#------------------------------------------------------------------------------ #$Date: 2024-05-26 01:14:09 +0300 (Sun, 26 May 2024) $ #$Revision: 292038 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/17/1571708.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1571708 loop_ _publ_author_name 'Prajapati, Bibek' 'Kwenda, Tendai' 'Lis, Tadeusz' 'Chmielewski, Piotr Jan' 'Gomez Garcia, Carlos J.' 'Majewski, Marcin A.' 'St\;epie\'n, Marcin' _publ_section_title ; Difluorenoheteroles: Topological Control of \p Conjugation in Diradicaloids and Mixed-Valence Radical Ions ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC02459A _journal_year 2024 _chemical_formula_moiety 'C60 H67 N' _chemical_formula_sum 'C60 H67 N' _chemical_formula_weight 802.14 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2023-06-28 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2023-10-22 deposited with the CCDC. 2024-05-21 downloaded from the CCDC. ; _cell_angle_alpha 105.22(4) _cell_angle_beta 91.86(4) _cell_angle_gamma 99.67(3) _cell_formula_units_Z 2 _cell_length_a 9.141(2) _cell_length_b 16.305(4) _cell_length_c 16.996(5) _cell_measurement_reflns_used 9733 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 50 _cell_measurement_theta_min 2.7 _cell_volume 2401.8(12) _computing_cell_refinement 'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type 'HyPix-Arc 150' _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.944 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix-Arc 150' _diffrn_measurement_method 'omega scan' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_unetI/netI 0.0713 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.944 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 31595 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.944 _diffrn_reflns_theta_full 67.000 _diffrn_reflns_theta_max 74.412 _diffrn_reflns_theta_min 2.703 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.467 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.600 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour red-pink _exptl_crystal_density_diffrn 1.109 _exptl_crystal_description needle _exptl_crystal_F_000 868 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.013 _refine_diff_density_max 0.438 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.092 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 567 _refine_ls_number_reflns 9269 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.1595 _refine_ls_R_factor_gt 0.1176 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+17.5749P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3186 _refine_ls_wR_factor_ref 0.3408 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5899 _reflns_number_total 9269 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02459a3.cif _cod_data_source_block tw044a _cod_depositor_comments ; The following automatic conversions were performed: data item '_atom_sites_solution_primary' value 'direct methods' was changed to 'direct'. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_database_code 1571708 _shelxl_version_number 2013-2 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.994 _shelx_estimated_absorpt_t_min 0.835 _olex2_refinement_description ; 1. Shared sites {C23A, C23C} 2. Uiso/Uaniso restraints and constraints Uanis(C23A) = Uanis(C23C) 3. Others Sof(C23C)=Sof(H23C)=Sof(C25C)=Sof(H25G)=Sof(H25H)=Sof(H25I)=1-FVAR(1) Sof(C23A)=Sof(H23A)=Sof(C25A)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1) 4.a Ternary CH refined with riding coordinates: C20A(H20A), C23A(H23A), C23C(H23C), C26A(H26A), C20B(H20B), C23B(H23B), C26B(H26B) 4.b Secondary CH2 refined with riding coordinates: C1(H11,H12), C2(H21,H22), C3(H31,H32) 4.c Me refined with riding coordinates: C24A(H24A,H24B,H24C), C25C(H25G,H25H,H25I) 4.d Aromatic/amide H refined with riding coordinates: C3A(H3A), C6A(H6A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C16A(H16A), C18A(H18A), C3B(H3B), C6B(H6B), C8B(H8B), C9B(H9B), C10B(H10B), C11B(H11B), C16B(H16B), C18B(H18B) 4.e Idealised Me refined as rotating group: C21A(H21A,H21B,H21C), C22A(H22A,H22B,H22C), C25A(H25A,H25B,H25C), C27A(H27A, H27B,H27C), C28A(H28A,H28B,H28C), C21B(H21D,H21E,H21F), C22B(H22D,H22E,H22F), C24B(H24D,H24E,H24F), C25B(H25D,H25E,H25F), C27B(H27D,H27E,H27F), C28B(H28D, H28E,H28F), C4(H41,H42,H43) ; _shelx_res_file ; TITL tw044 in P-1 CELL 1.54184 9.141 16.305 16.996 105.22 91.86 99.67 ZERR 2 0.002 0.004 0.005 0.04 0.04 0.03 LATT 1 SFAC C H N UNIT 120 134 2 acta 134 L.S. 10 size 0.013 0.03 0.40 PLAN 20 TEMP -173 BOND $H fmap 2 WGHT 0.077600 17.574900 FVAR 3.56512 0.80735 N1 3 0.273709 0.256494 0.614706 11.00000 0.03308 0.01544 = 0.03774 0.00900 -0.00320 -0.00197 C1A 1 0.387406 0.315337 0.666485 11.00000 0.02465 0.02799 = 0.03070 0.00696 -0.00055 0.00434 C2A 1 0.402265 0.394949 0.642969 11.00000 0.02845 0.02034 = 0.03228 0.00274 -0.00449 0.00006 C3A 1 0.511187 0.467650 0.685648 11.00000 0.02627 0.01979 = 0.03394 0.00469 0.00094 0.00152 AFIX 43 H3A 2 0.523285 0.520277 0.670396 11.00000 -1.20000 AFIX 0 C4A 1 0.597255 0.459489 0.748812 11.00000 0.03143 0.02492 = 0.03026 0.00451 -0.00312 0.00493 C5A 1 0.581279 0.378495 0.772618 11.00000 0.02888 0.02379 = 0.03507 0.01065 -0.00017 0.00032 C6A 1 0.473913 0.305829 0.730259 11.00000 0.02976 0.02382 = 0.03355 0.00837 0.00063 0.00296 AFIX 43 H6A 2 0.462021 0.252970 0.745087 11.00000 -1.20000 AFIX 0 C7A 1 0.718806 0.520179 0.802971 11.00000 0.02827 0.01965 = 0.03276 0.00632 0.00051 0.00087 C8A 1 0.785569 0.603328 0.807746 11.00000 0.03840 0.02500 = 0.03178 0.00375 -0.00190 0.00375 AFIX 43 H8A 2 0.751106 0.633241 0.771940 11.00000 -1.20000 AFIX 0 C9A 1 0.906952 0.644102 0.866967 11.00000 0.04285 0.03069 = 0.03703 0.00396 -0.00301 -0.00028 AFIX 43 H9A 2 0.953908 0.701767 0.870868 11.00000 -1.20000 AFIX 0 C10A 1 0.957277 0.600741 0.918865 11.00000 0.03983 0.03631 = 0.04068 0.00433 -0.00713 -0.00236 AFIX 43 H10A 2 1.039708 0.628508 0.957580 11.00000 -1.20000 AFIX 0 C11A 1 0.888690 0.516735 0.915188 11.00000 0.03833 0.03524 = 0.03869 0.00893 -0.01182 -0.00090 AFIX 43 H11A 2 0.921572 0.487570 0.952101 11.00000 -1.20000 AFIX 0 C12A 1 0.771307 0.476397 0.856539 11.00000 0.03800 0.02605 = 0.03193 0.00715 -0.00165 0.00063 C13A 1 0.685127 0.388871 0.837141 11.00000 0.03144 0.02276 = 0.03459 0.00872 -0.00077 0.00278 C14A 1 0.717777 0.323248 0.879329 11.00000 0.03144 0.02677 = 0.03202 0.01028 -0.00233 0.00294 C15A 1 0.648095 0.313045 0.949405 11.00000 0.03961 0.03584 = 0.03666 0.01176 0.00460 0.00576 C16A 1 0.686276 0.251729 0.986804 11.00000 0.04677 0.03703 = 0.04078 0.01795 0.00429 0.00361 AFIX 43 H16A 2 0.637570 0.243724 1.033484 11.00000 -1.20000 AFIX 0 C17A 1 0.793708 0.201858 0.957765 11.00000 0.04518 0.03058 = 0.04131 0.00867 -0.01005 0.00207 C18A 1 0.863458 0.215521 0.889875 11.00000 0.04124 0.03095 = 0.04899 0.00999 -0.00029 0.00971 AFIX 43 H18A 2 0.937049 0.182446 0.869464 11.00000 -1.20000 AFIX 0 C19A 1 0.830256 0.275537 0.850453 11.00000 0.03753 0.03274 = 0.03815 0.00915 -0.00084 0.00823 C20A 1 0.539014 0.369827 0.987894 11.00000 0.05064 0.06171 = 0.05570 0.02812 0.01747 0.02127 AFIX 13 H20A 2 0.528632 0.409409 0.952811 11.00000 -1.20000 AFIX 0 C21A 1 0.598633 0.426641 1.072665 11.00000 0.07931 0.05155 = 0.08034 -0.00165 0.02193 0.01831 AFIX 137 H21A 2 0.607034 0.390246 1.109619 11.00000 -1.50000 H21B 2 0.530369 0.466236 1.093384 11.00000 -1.50000 H21C 2 0.696940 0.460077 1.069656 11.00000 -1.50000 AFIX 0 C22A 1 0.385234 0.317962 0.988441 11.00000 0.04862 0.09840 = 0.08459 0.00424 0.00994 0.01343 AFIX 137 H22A 2 0.352235 0.280555 0.933323 11.00000 -1.50000 H22B 2 0.315348 0.357452 1.005797 11.00000 -1.50000 H22C 2 0.388678 0.282339 1.026558 11.00000 -1.50000 AFIX 0 part 1 C23A 1 0.835747 0.138336 1.001187 21.00000 0.05564 0.03545 = 0.05557 0.02168 -0.01470 -0.00039 AFIX 13 H23A 2 0.828925 0.161595 1.061295 21.00000 -1.20000 AFIX 0 part 0 C24A 1 0.994305 0.118562 0.985997 11.00000 0.08725 0.06955 = 0.07049 0.01900 -0.01280 0.02541 AFIX 33 H24A 2 1.018189 0.081293 1.019543 11.00000 -1.50000 H24B 2 1.066869 0.172790 1.000791 11.00000 -1.50000 H24C 2 0.997974 0.089118 0.928066 11.00000 -1.50000 AFIX 0 part 1 C25A 1 0.729716 0.052665 0.970586 21.00000 0.09185 0.03680 = 0.12965 0.05242 -0.05824 -0.02580 AFIX 137 H25A 2 0.727310 0.032831 0.910825 21.00000 -1.50000 H25B 2 0.629657 0.059849 0.986666 21.00000 -1.50000 H25C 2 0.763548 0.009860 0.994457 21.00000 -1.50000 AFIX 0 part 2 eadp c23a c23c exyz c23a c23c C23C 1 0.835747 0.138336 1.001187 -21.00000 0.05564 0.03545 = 0.05557 0.02168 -0.01470 -0.00039 AFIX 13 H23C 2 0.774400 0.083465 0.966111 -21.00000 -1.20000 AFIX 0 C25C 1 0.755282 0.145359 1.086916 -21.00000 0.04506 AFIX 33 H25G 2 0.785034 0.103477 1.113478 -21.00000 -1.50000 H25H 2 0.646917 0.132909 1.075224 -21.00000 -1.50000 H25I 2 0.785791 0.203889 1.123294 -21.00000 -1.50000 AFIX 0 part 0 C26A 1 0.914088 0.291592 0.779386 11.00000 0.04229 0.03613 = 0.05331 0.01451 0.01028 0.00864 AFIX 13 H26A 2 0.889564 0.345811 0.769660 11.00000 -1.20000 AFIX 0 C27A 1 0.864125 0.219301 0.700756 11.00000 0.05793 0.04614 = 0.05243 0.01734 0.01116 0.01426 AFIX 137 H27A 2 0.879450 0.164095 0.709282 11.00000 -1.50000 H27B 2 0.922576 0.231388 0.656437 11.00000 -1.50000 H27C 2 0.758317 0.216072 0.686136 11.00000 -1.50000 AFIX 0 C28A 1 1.083242 0.306922 0.797945 11.00000 0.04273 0.06223 = 0.07237 0.01459 0.01215 0.00124 AFIX 137 H28A 2 1.112760 0.354348 0.847829 11.00000 -1.50000 H28B 2 1.132968 0.322015 0.752100 11.00000 -1.50000 H28C 2 1.112137 0.254202 0.805772 11.00000 -1.50000 AFIX 0 C1B 1 0.216790 0.294373 0.559402 11.00000 0.02763 0.02488 = 0.03050 0.00788 0.00244 -0.00019 C2B 1 0.297623 0.382701 0.576794 11.00000 0.02793 0.02118 = 0.03173 0.00921 -0.00026 0.00189 C3B 1 0.260484 0.437365 0.529162 11.00000 0.02902 0.01852 = 0.03262 0.00651 0.00437 0.00166 AFIX 43 H3B 2 0.312499 0.495185 0.539588 11.00000 -1.20000 AFIX 0 C4B 1 0.150746 0.405504 0.469417 11.00000 0.02446 0.01880 = 0.03307 0.00674 0.00451 -0.00105 C5B 1 0.068988 0.315624 0.451131 11.00000 0.02603 0.01921 = 0.03368 0.00404 0.00280 -0.00294 C6B 1 0.104807 0.260870 0.498319 11.00000 0.03225 0.02203 = 0.03686 0.00541 -0.00185 0.00009 AFIX 43 H6B 2 0.052972 0.203015 0.487929 11.00000 -1.20000 AFIX 0 C7B 1 0.084303 0.444589 0.411178 11.00000 0.02188 0.02597 = 0.03526 0.01278 0.00249 0.00280 C8B 1 0.112534 0.527833 0.402896 11.00000 0.03096 0.03155 = 0.03618 0.00984 0.00258 0.00245 AFIX 43 H8B 2 0.187644 0.570683 0.437516 11.00000 -1.20000 AFIX 0 C9B 1 0.028197 0.547675 0.342471 11.00000 0.03151 0.03490 = 0.04157 0.01878 0.00405 0.00578 AFIX 43 H9B 2 0.046417 0.604495 0.335876 11.00000 -1.20000 AFIX 0 C10B 1 -0.082439 0.484673 0.291832 11.00000 0.03890 0.03227 = 0.03909 0.01522 0.00346 0.00643 AFIX 43 H10B 2 -0.138597 0.498895 0.250910 11.00000 -1.20000 AFIX 0 C11B 1 -0.111338 0.400484 0.300913 11.00000 0.02835 0.03603 = 0.03607 0.00896 0.00308 -0.00025 AFIX 43 H11B 2 -0.186749 0.357725 0.266430 11.00000 -1.20000 AFIX 0 C12B 1 -0.029364 0.380624 0.360211 11.00000 0.02947 0.02829 = 0.03229 0.00602 0.00045 0.00662 C13B 1 -0.035734 0.300916 0.385377 11.00000 0.02580 0.02271 = 0.03886 0.00905 0.00323 0.00439 C14B 1 -0.136045 0.217730 0.343135 11.00000 0.02674 0.02744 = 0.03666 0.00594 -0.00138 0.00201 C15B 1 -0.292380 0.211827 0.344831 11.00000 0.03216 0.02229 = 0.04055 0.00704 -0.00096 0.00052 C16B 1 -0.384456 0.135675 0.300956 11.00000 0.02780 0.03323 = 0.04740 0.01014 -0.00536 -0.00367 AFIX 43 H16B 2 -0.489114 0.131893 0.302542 11.00000 -1.20000 AFIX 0 C17B 1 -0.330901 0.064730 0.254841 11.00000 0.03546 0.03323 = 0.04390 0.01039 -0.00589 -0.00602 C18B 1 -0.176099 0.071794 0.255367 11.00000 0.03713 0.02615 = 0.03991 0.00341 -0.00304 0.00054 AFIX 43 H18B 2 -0.136215 0.023948 0.225161 11.00000 -1.20000 AFIX 0 C19B 1 -0.077655 0.146992 0.298896 11.00000 0.02708 0.03131 = 0.03288 0.00908 -0.00092 0.00129 C20B 1 -0.359279 0.283269 0.400306 11.00000 0.02603 0.02963 = 0.04984 0.00882 0.00378 0.00415 AFIX 13 H20B 2 -0.284060 0.337934 0.411492 11.00000 -1.20000 AFIX 0 C21B 1 -0.501531 0.299070 0.361253 11.00000 0.03845 0.04706 = 0.08981 0.00601 -0.00888 0.01873 AFIX 137 H21D 2 -0.481783 0.310312 0.308356 11.00000 -1.50000 H21E 2 -0.533981 0.349118 0.397339 11.00000 -1.50000 H21F 2 -0.579883 0.247893 0.353066 11.00000 -1.50000 AFIX 0 C22B 1 -0.389176 0.264677 0.481993 11.00000 0.05271 0.03519 = 0.06313 0.01817 0.02060 0.01123 AFIX 137 H22D 2 -0.462043 0.210997 0.473005 11.00000 -1.50000 H22E 2 -0.428541 0.312526 0.517274 11.00000 -1.50000 H22F 2 -0.296212 0.258524 0.508351 11.00000 -1.50000 AFIX 0 C23B 1 -0.438598 -0.015465 0.206851 11.00000 0.04130 0.03486 = 0.04892 0.00556 -0.00799 -0.00686 AFIX 13 H23B 2 -0.511893 0.002373 0.172664 11.00000 -1.20000 AFIX 0 C24B 1 -0.523699 -0.059993 0.264716 11.00000 0.04248 0.04232 = 0.08774 0.01431 -0.00402 -0.00721 AFIX 137 H24D 2 -0.453936 -0.080793 0.296520 11.00000 -1.50000 H24E 2 -0.598018 -0.109008 0.232811 11.00000 -1.50000 H24F 2 -0.573730 -0.018741 0.301934 11.00000 -1.50000 AFIX 0 C25B 1 -0.362586 -0.084000 0.149840 11.00000 0.08348 0.04901 = 0.07000 -0.00929 -0.00578 -0.01202 AFIX 137 H25D 2 -0.295321 -0.105059 0.182849 11.00000 -1.50000 H25E 2 -0.305662 -0.057788 0.111922 11.00000 -1.50000 H25F 2 -0.438757 -0.132450 0.118732 11.00000 -1.50000 AFIX 0 C26B 1 0.087898 0.147582 0.293628 11.00000 0.03183 0.03062 = 0.03854 0.00517 -0.00043 0.00117 AFIX 13 H26B 2 0.141755 0.202384 0.332614 11.00000 -1.20000 AFIX 0 C27B 1 0.135052 0.072686 0.319751 11.00000 0.03835 0.04816 = 0.06104 0.02194 0.00306 0.01256 AFIX 137 H27D 2 0.109014 0.075688 0.375792 11.00000 -1.50000 H27E 2 0.242878 0.076402 0.317440 11.00000 -1.50000 H27F 2 0.083581 0.017815 0.282816 11.00000 -1.50000 AFIX 0 C28B 1 0.134975 0.147731 0.208636 11.00000 0.05050 0.04495 = 0.04891 0.01694 0.01122 0.00557 AFIX 137 H28D 2 0.088031 0.093324 0.169283 11.00000 -1.50000 H28E 2 0.243482 0.153686 0.208881 11.00000 -1.50000 H28F 2 0.103742 0.196279 0.192986 11.00000 -1.50000 AFIX 0 C1 1 0.221711 0.167366 0.616746 11.00000 0.02573 0.02552 = 0.04193 0.01282 0.00102 0.00090 AFIX 23 H11 2 0.112217 0.153159 0.605012 11.00000 -1.20000 H12 2 0.244366 0.162704 0.672596 11.00000 -1.20000 AFIX 0 C2 1 0.290570 0.102087 0.556636 11.00000 0.04427 0.02224 = 0.04316 0.00756 0.00060 0.00221 AFIX 23 H21 2 0.398244 0.110495 0.572764 11.00000 -1.20000 H22 2 0.279626 0.111210 0.501569 11.00000 -1.20000 AFIX 0 C3 1 0.217420 0.010615 0.553503 11.00000 0.04298 0.02380 = 0.05254 0.01099 -0.00312 -0.00009 AFIX 23 H31 2 0.229269 0.002051 0.608746 11.00000 -1.20000 H32 2 0.109482 0.003254 0.538599 11.00000 -1.20000 AFIX 0 C4 1 0.279977 -0.057792 0.493643 11.00000 0.08940 0.02526 = 0.09334 0.00203 0.02383 0.00856 AFIX 137 H41 2 0.269134 -0.049761 0.438734 11.00000 -1.50000 H42 2 0.225894 -0.115060 0.493548 11.00000 -1.50000 H43 2 0.385661 -0.053124 0.509644 11.00000 -1.50000 AFIX 0 HKLF 4 REM tw044 in P-1 REM R1 = 0.1176 for 5899 Fo > 4sig(Fo) and 0.1595 for all 9269 data REM 567 parameters refined using 0 restraints END WGHT 0.0856 15.9163 REM Highest difference peak 0.438, deepest hole -0.492, 1-sigma level 0.092 Q1 1 -0.4195 -0.0277 0.1129 11.00000 0.05 0.44 Q2 1 0.4602 -0.0136 0.4809 11.00000 0.05 0.40 Q3 1 0.2284 0.4183 0.4001 11.00000 0.05 0.40 Q4 1 -0.1657 0.5633 0.2045 11.00000 0.05 0.39 Q5 1 0.0577 0.1462 0.5991 11.00000 0.05 0.38 Q6 1 0.5000 0.0000 0.5000 10.50000 0.05 0.37 Q7 1 -0.3626 0.2923 0.6043 11.00000 0.05 0.35 Q8 1 1.0516 0.1661 0.8011 11.00000 0.05 0.34 Q9 1 0.3153 0.1147 0.3406 11.00000 0.05 0.34 Q10 1 1.0098 0.2132 0.6664 11.00000 0.05 0.34 Q11 1 -0.1793 0.2049 0.2878 11.00000 0.05 0.34 Q12 1 0.0192 0.1740 0.4851 11.00000 0.05 0.33 Q13 1 0.2403 0.1144 0.2552 11.00000 0.05 0.32 Q14 1 0.0143 0.2001 0.4278 11.00000 0.05 0.32 Q15 1 0.9118 0.2358 1.0363 11.00000 0.05 0.32 Q16 1 0.2016 -0.0458 0.3148 11.00000 0.05 0.32 Q17 1 -0.5842 0.1622 0.3836 11.00000 0.05 0.32 Q18 1 -0.0183 0.3585 0.2341 11.00000 0.05 0.32 Q19 1 0.8572 0.0454 0.9489 11.00000 0.05 0.32 Q20 1 0.1016 0.1591 0.5181 11.00000 0.05 0.32 ; _shelx_res_checksum 64360 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.732 _oxdiff_exptl_absorpt_empirical_full_min 0.685 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.2737(5) 0.2565(3) 0.6147(3) 0.0293(10) Uani 1 1 d . . . . . C1A C 0.3874(6) 0.3153(3) 0.6665(3) 0.0281(11) Uani 1 1 d . . . . . C2A C 0.4023(6) 0.3949(3) 0.6430(3) 0.0286(12) Uani 1 1 d . . . . . C3A C 0.5112(6) 0.4677(3) 0.6856(3) 0.0275(11) Uani 1 1 d . . . . . H3A H 0.5233 0.5203 0.6704 0.033 Uiso 1 1 calc R U . . . C4A C 0.5973(6) 0.4595(3) 0.7488(3) 0.0296(12) Uani 1 1 d . . . . . C5A C 0.5813(6) 0.3785(3) 0.7726(3) 0.0293(12) Uani 1 1 d . . . . . C6A C 0.4739(6) 0.3058(3) 0.7303(3) 0.0292(12) Uani 1 1 d . . . . . H6A H 0.4620 0.2530 0.7451 0.035 Uiso 1 1 calc R U . . . C7A C 0.7188(6) 0.5202(3) 0.8030(3) 0.0275(11) Uani 1 1 d . . . . . C8A C 0.7856(7) 0.6033(3) 0.8077(3) 0.0328(13) Uani 1 1 d . . . . . H8A H 0.7511 0.6332 0.7719 0.039 Uiso 1 1 calc R U . . . C9A C 0.9070(7) 0.6441(4) 0.8670(4) 0.0388(14) Uani 1 1 d . . . . . H9A H 0.9539 0.7018 0.8709 0.047 Uiso 1 1 calc R U . . . C10A C 0.9573(7) 0.6007(4) 0.9189(4) 0.0415(15) Uani 1 1 d . . . . . H10A H 1.0397 0.6285 0.9576 0.050 Uiso 1 1 calc R U . . . C11A C 0.8887(7) 0.5167(4) 0.9152(4) 0.0389(14) Uani 1 1 d . . . . . H11A H 0.9216 0.4876 0.9521 0.047 Uiso 1 1 calc R U . . . C12A C 0.7713(7) 0.4764(4) 0.8565(3) 0.0329(13) Uani 1 1 d . . . . . C13A C 0.6851(6) 0.3889(3) 0.8371(3) 0.0298(12) Uani 1 1 d . . . . . C14A C 0.7178(6) 0.3232(3) 0.8793(3) 0.0300(12) Uani 1 1 d . . . . . C15A C 0.6481(7) 0.3130(4) 0.9494(4) 0.0371(13) Uani 1 1 d . . . . . C16A C 0.6863(7) 0.2517(4) 0.9868(4) 0.0406(14) Uani 1 1 d . . . . . H16A H 0.6376 0.2437 1.0335 0.049 Uiso 1 1 calc R U . . . C17A C 0.7937(7) 0.2019(4) 0.9578(4) 0.0401(14) Uani 1 1 d . . . . . C18A C 0.8635(7) 0.2155(4) 0.8899(4) 0.0403(14) Uani 1 1 d . . . . . H18A H 0.9370 0.1824 0.8695 0.048 Uiso 1 1 calc R U . . . C19A C 0.8303(7) 0.2755(4) 0.8505(4) 0.0361(13) Uani 1 1 d . . . . . C20A C 0.5390(8) 0.3698(5) 0.9879(5) 0.0521(18) Uani 1 1 d . . . . . H20A H 0.5286 0.4094 0.9528 0.062 Uiso 1 1 calc R U . . . C21A C 0.5986(10) 0.4266(5) 1.0727(5) 0.073(3) Uani 1 1 d . . . . . H21A H 0.6070 0.3902 1.1096 0.110 Uiso 1 1 calc R U . . . H21B H 0.5304 0.4662 1.0934 0.110 Uiso 1 1 calc R U . . . H21C H 0.6969 0.4601 1.0697 0.110 Uiso 1 1 calc R U . . . C22A C 0.3852(9) 0.3180(7) 0.9884(6) 0.081(3) Uani 1 1 d . . . . . H22A H 0.3522 0.2806 0.9333 0.122 Uiso 1 1 calc R U . . . H22B H 0.3153 0.3575 1.0058 0.122 Uiso 1 1 calc R U . . . H22C H 0.3887 0.2823 1.0266 0.122 Uiso 1 1 calc R U . . . C23A C 0.8357(8) 0.1383(4) 1.0012(5) 0.0486(17) Uani 0.807(15) 1 d . . P A 1 H23A H 0.8289 0.1616 1.0613 0.058 Uiso 0.807(15) 1 calc R U P A 1 C24A C 0.9943(11) 0.1186(6) 0.9860(6) 0.075(3) Uani 1 1 d . . . . . H24A H 1.0182 0.0813 1.0195 0.112 Uiso 1 1 calc R U . A 1 H24B H 1.0669 0.1728 1.0008 0.112 Uiso 1 1 calc R U . A 1 H24C H 0.9980 0.0891 0.9281 0.112 Uiso 1 1 calc R U . A 1 C25A C 0.7297(13) 0.0527(6) 0.9706(8) 0.086(5) Uani 0.807(15) 1 d . . P A 1 H25A H 0.7273 0.0328 0.9108 0.130 Uiso 0.807(15) 1 calc R U P A 1 H25B H 0.6297 0.0598 0.9867 0.130 Uiso 0.807(15) 1 calc R U P A 1 H25C H 0.7635 0.0099 0.9945 0.130 Uiso 0.807(15) 1 calc R U P A 1 C23C C 0.8357(8) 0.1383(4) 1.0012(5) 0.0486(17) Uani 0.193(15) 1 d . . P A 2 H23C H 0.7744 0.0835 0.9661 0.058 Uiso 0.193(15) 1 calc R U P A 2 C25C C 0.755(4) 0.145(2) 1.087(2) 0.045(10) Uiso 0.193(15) 1 d . . P A 2 H25G H 0.7850 0.1035 1.1135 0.068 Uiso 0.193(15) 1 calc R U P A 2 H25H H 0.6469 0.1329 1.0752 0.068 Uiso 0.193(15) 1 calc R U P A 2 H25I H 0.7858 0.2039 1.1233 0.068 Uiso 0.193(15) 1 calc R U P A 2 C26A C 0.9141(7) 0.2916(4) 0.7794(4) 0.0431(15) Uani 1 1 d . . . . . H26A H 0.8896 0.3458 0.7697 0.052 Uiso 1 1 calc R U . . . C27A C 0.8641(8) 0.2193(4) 0.7008(4) 0.0507(17) Uani 1 1 d . . . . . H27A H 0.8794 0.1641 0.7093 0.076 Uiso 1 1 calc R U . . . H27B H 0.9226 0.2314 0.6564 0.076 Uiso 1 1 calc R U . . . H27C H 0.7583 0.2161 0.6861 0.076 Uiso 1 1 calc R U . . . C28A C 1.0832(8) 0.3069(5) 0.7979(5) 0.061(2) Uani 1 1 d . . . . . H28A H 1.1128 0.3543 0.8478 0.091 Uiso 1 1 calc R U . . . H28B H 1.1330 0.3220 0.7521 0.091 Uiso 1 1 calc R U . . . H28C H 1.1121 0.2542 0.8058 0.091 Uiso 1 1 calc R U . . . C1B C 0.2168(6) 0.2944(3) 0.5594(3) 0.0282(11) Uani 1 1 d . . . . . C2B C 0.2976(6) 0.3827(3) 0.5768(3) 0.0269(11) Uani 1 1 d . . . . . C3B C 0.2605(6) 0.4374(3) 0.5292(3) 0.0271(11) Uani 1 1 d . . . . . H3B H 0.3125 0.4952 0.5396 0.033 Uiso 1 1 calc R U . . . C4B C 0.1507(6) 0.4055(3) 0.4694(3) 0.0261(11) Uani 1 1 d . . . . . C5B C 0.0690(6) 0.3156(3) 0.4511(3) 0.0278(11) Uani 1 1 d . . . . . C6B C 0.1048(6) 0.2609(3) 0.4983(3) 0.0316(12) Uani 1 1 d . . . . . H6B H 0.0530 0.2030 0.4879 0.038 Uiso 1 1 calc R U . . . C7B C 0.0843(6) 0.4446(3) 0.4112(3) 0.0270(11) Uani 1 1 d . . . . . C8B C 0.1125(6) 0.5278(4) 0.4029(4) 0.0332(12) Uani 1 1 d . . . . . H8B H 0.1876 0.5707 0.4375 0.040 Uiso 1 1 calc R U . . . C9B C 0.0282(6) 0.5477(4) 0.3425(4) 0.0344(13) Uani 1 1 d . . . . . H9B H 0.0464 0.6045 0.3359 0.041 Uiso 1 1 calc R U . . . C10B C -0.0824(7) 0.4847(4) 0.2918(4) 0.0357(13) Uani 1 1 d . . . . . H10B H -0.1386 0.4989 0.2509 0.043 Uiso 1 1 calc R U . . . C11B C -0.1113(6) 0.4005(4) 0.3009(4) 0.0344(13) Uani 1 1 d . . . . . H11B H -0.1867 0.3577 0.2664 0.041 Uiso 1 1 calc R U . . . C12B C -0.0294(6) 0.3806(3) 0.3602(3) 0.0303(12) Uani 1 1 d . . . . . C13B C -0.0357(6) 0.3009(3) 0.3854(3) 0.0290(12) Uani 1 1 d . . . . . C14B C -0.1360(6) 0.2177(3) 0.3431(3) 0.0313(12) Uani 1 1 d . . . . . C15B C -0.2924(6) 0.2118(3) 0.3448(4) 0.0326(12) Uani 1 1 d . . . . . C16B C -0.3845(7) 0.1357(4) 0.3010(4) 0.0376(14) Uani 1 1 d . . . . . H16B H -0.4891 0.1319 0.3025 0.045 Uiso 1 1 calc R U . . . C17B C -0.3309(7) 0.0647(4) 0.2548(4) 0.0392(14) Uani 1 1 d . . . . . C18B C -0.1761(7) 0.0718(4) 0.2554(4) 0.0362(13) Uani 1 1 d . . . . . H18B H -0.1362 0.0239 0.2252 0.043 Uiso 1 1 calc R U . . . C19B C -0.0777(6) 0.1470(4) 0.2989(3) 0.0309(12) Uani 1 1 d . . . . . C20B C -0.3593(6) 0.2833(4) 0.4003(4) 0.0356(13) Uani 1 1 d . . . . . H20B H -0.2841 0.3379 0.4115 0.043 Uiso 1 1 calc R U . . . C21B C -0.5015(8) 0.2991(5) 0.3613(5) 0.060(2) Uani 1 1 d . . . . . H21D H -0.4818 0.3103 0.3084 0.090 Uiso 1 1 calc R U . . . H21E H -0.5340 0.3491 0.3973 0.090 Uiso 1 1 calc R U . . . H21F H -0.5799 0.2479 0.3531 0.090 Uiso 1 1 calc R U . . . C22B C -0.3892(8) 0.2647(4) 0.4820(4) 0.0487(17) Uani 1 1 d . . . . . H22D H -0.4620 0.2110 0.4730 0.073 Uiso 1 1 calc R U . . . H22E H -0.4285 0.3125 0.5173 0.073 Uiso 1 1 calc R U . . . H22F H -0.2962 0.2585 0.5084 0.073 Uiso 1 1 calc R U . . . C23B C -0.4386(7) -0.0155(4) 0.2069(4) 0.0447(16) Uani 1 1 d . . . . . H23B H -0.5119 0.0024 0.1727 0.054 Uiso 1 1 calc R U . . . C24B C -0.5237(8) -0.0600(5) 0.2647(5) 0.060(2) Uani 1 1 d . . . . . H24D H -0.4539 -0.0808 0.2965 0.090 Uiso 1 1 calc R U . . . H24E H -0.5980 -0.1090 0.2328 0.090 Uiso 1 1 calc R U . . . H24F H -0.5737 -0.0187 0.3019 0.090 Uiso 1 1 calc R U . . . C25B C -0.3626(11) -0.0840(5) 0.1498(5) 0.076(3) Uani 1 1 d . . . . . H25D H -0.2953 -0.1051 0.1828 0.113 Uiso 1 1 calc R U . . . H25E H -0.3057 -0.0578 0.1119 0.113 Uiso 1 1 calc R U . . . H25F H -0.4388 -0.1324 0.1187 0.113 Uiso 1 1 calc R U . . . C26B C 0.0879(6) 0.1476(4) 0.2936(4) 0.0351(13) Uani 1 1 d . . . . . H26B H 0.1418 0.2024 0.3326 0.042 Uiso 1 1 calc R U . . . C27B C 0.1351(7) 0.0727(4) 0.3198(5) 0.0473(16) Uani 1 1 d . . . . . H27D H 0.1090 0.0757 0.3758 0.071 Uiso 1 1 calc R U . . . H27E H 0.2429 0.0764 0.3174 0.071 Uiso 1 1 calc R U . . . H27F H 0.0836 0.0178 0.2828 0.071 Uiso 1 1 calc R U . . . C28B C 0.1350(8) 0.1477(4) 0.2086(4) 0.0475(16) Uani 1 1 d . . . . . H28D H 0.0880 0.0933 0.1693 0.071 Uiso 1 1 calc R U . . . H28E H 0.2435 0.1537 0.2089 0.071 Uiso 1 1 calc R U . . . H28F H 0.1037 0.1963 0.1930 0.071 Uiso 1 1 calc R U . . . C1 C 0.2217(6) 0.1674(3) 0.6167(4) 0.0309(12) Uani 1 1 d . . . . . H11 H 0.1122 0.1532 0.6050 0.037 Uiso 1 1 calc R U . . . H12 H 0.2444 0.1627 0.6726 0.037 Uiso 1 1 calc R U . . . C2 C 0.2906(7) 0.1021(3) 0.5566(4) 0.0373(14) Uani 1 1 d . . . . . H21 H 0.3982 0.1105 0.5728 0.045 Uiso 1 1 calc R U . . . H22 H 0.2796 0.1112 0.5016 0.045 Uiso 1 1 calc R U . . . C3 C 0.2174(7) 0.0106(4) 0.5535(4) 0.0406(15) Uani 1 1 d . . . . . H31 H 0.2293 0.0021 0.6087 0.049 Uiso 1 1 calc R U . . . H32 H 0.1095 0.0033 0.5386 0.049 Uiso 1 1 calc R U . . . C4 C 0.2800(10) -0.0578(4) 0.4936(6) 0.072(3) Uani 1 1 d . . . . . H41 H 0.2691 -0.0498 0.4387 0.108 Uiso 1 1 calc R U . . . H42 H 0.2259 -0.1151 0.4935 0.108 Uiso 1 1 calc R U . . . H43 H 0.3857 -0.0531 0.5096 0.108 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.033(2) 0.015(2) 0.038(3) 0.0090(18) -0.003(2) -0.0020(18) C1A 0.025(3) 0.028(3) 0.031(3) 0.007(2) -0.001(2) 0.004(2) C2A 0.028(3) 0.020(3) 0.032(3) 0.003(2) -0.004(2) 0.000(2) C3A 0.026(3) 0.020(2) 0.034(3) 0.005(2) 0.001(2) 0.002(2) C4A 0.031(3) 0.025(3) 0.030(3) 0.005(2) -0.003(2) 0.005(2) C5A 0.029(3) 0.024(3) 0.035(3) 0.011(2) 0.000(2) 0.000(2) C6A 0.030(3) 0.024(3) 0.034(3) 0.008(2) 0.001(2) 0.003(2) C7A 0.028(3) 0.020(2) 0.033(3) 0.006(2) 0.001(2) 0.001(2) C8A 0.038(3) 0.025(3) 0.032(3) 0.004(2) -0.002(2) 0.004(2) C9A 0.043(4) 0.031(3) 0.037(3) 0.004(3) -0.003(3) 0.000(3) C10A 0.040(3) 0.036(3) 0.041(4) 0.004(3) -0.007(3) -0.002(3) C11A 0.038(3) 0.035(3) 0.039(3) 0.009(3) -0.012(3) -0.001(3) C12A 0.038(3) 0.026(3) 0.032(3) 0.007(2) -0.002(2) 0.001(2) C13A 0.031(3) 0.023(3) 0.035(3) 0.009(2) -0.001(2) 0.003(2) C14A 0.031(3) 0.027(3) 0.032(3) 0.010(2) -0.002(2) 0.003(2) C15A 0.040(3) 0.036(3) 0.037(3) 0.012(3) 0.005(3) 0.006(3) C16A 0.047(4) 0.037(3) 0.041(3) 0.018(3) 0.004(3) 0.004(3) C17A 0.045(4) 0.031(3) 0.041(4) 0.009(3) -0.010(3) 0.002(3) C18A 0.041(3) 0.031(3) 0.049(4) 0.010(3) 0.000(3) 0.010(3) C19A 0.038(3) 0.033(3) 0.038(3) 0.009(3) -0.001(3) 0.008(2) C20A 0.051(4) 0.062(5) 0.056(4) 0.028(4) 0.017(3) 0.021(4) C21A 0.079(6) 0.052(5) 0.080(6) -0.002(4) 0.022(5) 0.018(4) C22A 0.049(5) 0.098(7) 0.085(7) 0.004(5) 0.010(4) 0.013(5) C23A 0.056(4) 0.035(3) 0.056(4) 0.022(3) -0.015(3) 0.000(3) C24A 0.087(7) 0.070(6) 0.070(6) 0.019(5) -0.013(5) 0.025(5) C25A 0.092(8) 0.037(5) 0.130(10) 0.052(6) -0.058(7) -0.026(5) C23C 0.056(4) 0.035(3) 0.056(4) 0.022(3) -0.015(3) 0.000(3) C26A 0.042(4) 0.036(3) 0.053(4) 0.015(3) 0.010(3) 0.009(3) C27A 0.058(4) 0.046(4) 0.052(4) 0.017(3) 0.011(3) 0.014(3) C28A 0.043(4) 0.062(5) 0.072(5) 0.015(4) 0.012(4) 0.001(3) C1B 0.028(3) 0.025(3) 0.030(3) 0.008(2) 0.002(2) 0.000(2) C2B 0.028(3) 0.021(2) 0.032(3) 0.009(2) 0.000(2) 0.002(2) C3B 0.029(3) 0.019(2) 0.033(3) 0.007(2) 0.004(2) 0.002(2) C4B 0.024(3) 0.019(2) 0.033(3) 0.007(2) 0.005(2) -0.001(2) C5B 0.026(3) 0.019(2) 0.034(3) 0.004(2) 0.003(2) -0.003(2) C6B 0.032(3) 0.022(3) 0.037(3) 0.005(2) -0.002(2) 0.000(2) C7B 0.022(3) 0.026(3) 0.035(3) 0.013(2) 0.002(2) 0.003(2) C8B 0.031(3) 0.032(3) 0.036(3) 0.010(2) 0.003(2) 0.002(2) C9B 0.032(3) 0.035(3) 0.042(3) 0.019(3) 0.004(2) 0.006(2) C10B 0.039(3) 0.032(3) 0.039(3) 0.015(3) 0.003(3) 0.006(2) C11B 0.028(3) 0.036(3) 0.036(3) 0.009(2) 0.003(2) 0.000(2) C12B 0.029(3) 0.028(3) 0.032(3) 0.006(2) 0.000(2) 0.007(2) C13B 0.026(3) 0.023(3) 0.039(3) 0.009(2) 0.003(2) 0.004(2) C14B 0.027(3) 0.027(3) 0.037(3) 0.006(2) -0.001(2) 0.002(2) C15B 0.032(3) 0.022(3) 0.041(3) 0.007(2) -0.001(2) 0.001(2) C16B 0.028(3) 0.033(3) 0.047(4) 0.010(3) -0.005(3) -0.004(2) C17B 0.035(3) 0.033(3) 0.044(4) 0.010(3) -0.006(3) -0.006(3) C18B 0.037(3) 0.026(3) 0.040(3) 0.003(2) -0.003(3) 0.001(2) C19B 0.027(3) 0.031(3) 0.033(3) 0.009(2) -0.001(2) 0.001(2) C20B 0.026(3) 0.030(3) 0.050(4) 0.009(3) 0.004(3) 0.004(2) C21B 0.038(4) 0.047(4) 0.090(6) 0.006(4) -0.009(4) 0.019(3) C22B 0.053(4) 0.035(3) 0.063(5) 0.018(3) 0.021(3) 0.011(3) C23B 0.041(4) 0.035(3) 0.049(4) 0.006(3) -0.008(3) -0.007(3) C24B 0.042(4) 0.042(4) 0.088(6) 0.014(4) -0.004(4) -0.007(3) C25B 0.083(6) 0.049(5) 0.070(6) -0.009(4) -0.006(5) -0.012(4) C26B 0.032(3) 0.031(3) 0.039(3) 0.005(2) 0.000(2) 0.001(2) C27B 0.038(4) 0.048(4) 0.061(4) 0.022(3) 0.003(3) 0.013(3) C28B 0.050(4) 0.045(4) 0.049(4) 0.017(3) 0.011(3) 0.006(3) C1 0.026(3) 0.026(3) 0.042(3) 0.013(2) 0.001(2) 0.001(2) C2 0.044(4) 0.022(3) 0.043(3) 0.008(2) 0.001(3) 0.002(2) C3 0.043(4) 0.024(3) 0.053(4) 0.011(3) -0.003(3) 0.000(3) C4 0.089(6) 0.025(3) 0.093(6) 0.002(4) 0.024(5) 0.009(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1A N1 C1 125.7(4) . . ? C1B N1 C1A 110.0(4) . . ? C1B N1 C1 124.3(4) . . ? N1 C1A C2A 107.3(4) . . ? C6A C1A N1 129.9(5) . . ? C6A C1A C2A 122.8(5) . . ? C3A C2A C1A 120.0(5) . . ? C2B C2A C1A 108.1(4) . . ? C2B C2A C3A 131.9(5) . . ? C2A C3A H3A 121.0 . . ? C4A C3A C2A 118.0(5) . . ? C4A C3A H3A 121.0 . . ? C3A C4A C5A 121.7(5) . . ? C3A C4A C7A 131.4(5) . . ? C7A C4A C5A 106.8(4) . . ? C6A C5A C4A 120.6(5) . . ? C13A C5A C4A 108.7(5) . . ? C13A C5A C6A 130.6(5) . . ? C1A C6A C5A 116.8(5) . . ? C1A C6A H6A 121.6 . . ? C5A C6A H6A 121.6 . . ? C8A C7A C4A 133.0(5) . . ? C8A C7A C12A 119.9(5) . . ? C12A C7A C4A 107.1(4) . . ? C7A C8A H8A 120.5 . . ? C7A C8A C9A 119.0(5) . . ? C9A C8A H8A 120.5 . . ? C8A C9A H9A 119.7 . . ? C10A C9A C8A 120.6(6) . . ? C10A C9A H9A 119.7 . . ? C9A C10A H10A 119.6 . . ? C9A C10A C11A 120.7(6) . . ? C11A C10A H10A 119.6 . . ? C10A C11A H11A 120.6 . . ? C12A C11A C10A 118.7(6) . . ? C12A C11A H11A 120.6 . . ? C7A C12A C13A 109.0(5) . . ? C11A C12A C7A 121.0(5) . . ? C11A C12A C13A 130.0(5) . . ? C5A C13A C12A 108.4(5) . . ? C5A C13A C14A 128.6(5) . . ? C12A C13A C14A 122.8(5) . . ? C15A C14A C13A 121.7(5) . . ? C15A C14A C19A 120.0(5) . . ? C19A C14A C13A 118.1(5) . . ? C14A C15A C20A 121.7(5) . . ? C16A C15A C14A 118.7(6) . . ? C16A C15A C20A 119.5(6) . . ? C15A C16A H16A 118.9 . . ? C17A C16A C15A 122.3(6) . . ? C17A C16A H16A 118.9 . . ? C16A C17A C23A 120.9(6) . . ? C18A C17A C16A 117.4(6) . . ? C18A C17A C23A 121.6(6) . . ? C17A C18A H18A 118.6 . . ? C17A C18A C19A 122.8(6) . . ? C19A C18A H18A 118.6 . . ? C14A C19A C26A 120.1(5) . . ? C18A C19A C14A 118.8(6) . . ? C18A C19A C26A 121.1(6) . . ? C15A C20A H20A 106.9 . . ? C21A C20A C15A 111.7(6) . . ? C21A C20A H20A 106.9 . . ? C22A C20A C15A 112.3(7) . . ? C22A C20A H20A 106.9 . . ? C22A C20A C21A 111.8(7) . . ? C20A C21A H21A 109.5 . . ? C20A C21A H21B 109.5 . . ? C20A C21A H21C 109.5 . . ? H21A C21A H21B 109.5 . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? C20A C22A H22A 109.5 . . ? C20A C22A H22B 109.5 . . ? C20A C22A H22C 109.5 . . ? H22A C22A H22B 109.5 . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? C17A C23A H23A 109.1 . . ? C17A C23A C24A 113.5(6) . . ? C17A C23A C25A 109.7(6) . . ? C24A C23A H23A 109.1 . . ? C25A C23A H23A 109.1 . . ? C25A C23A C24A 106.2(8) . . ? C23A C24A H24A 109.5 . . ? C23A C24A H24B 109.5 . . ? C23A C24A H24C 109.5 . . ? H24A C24A H24B 109.5 . . ? H24A C24A H24C 109.5 . . ? H24B C24A H24C 109.5 . . ? C23A C25A H25A 109.5 . . ? C23A C25A H25B 109.5 . . ? C23A C25A H25C 109.5 . . ? H25A C25A H25B 109.5 . . ? H25A C25A H25C 109.5 . . ? H25B C25A H25C 109.5 . . ? H25G C25C H25H 109.5 . . ? H25G C25C H25I 109.5 . . ? H25H C25C H25I 109.5 . . ? C19A C26A H26A 107.1 . . ? C19A C26A C27A 111.9(5) . . ? C19A C26A C28A 112.4(6) . . ? C27A C26A H26A 107.1 . . ? C27A C26A C28A 111.0(6) . . ? C28A C26A H26A 107.1 . . ? C26A C27A H27A 109.5 . . ? C26A C27A H27B 109.5 . . ? C26A C27A H27C 109.5 . . ? H27A C27A H27B 109.5 . . ? H27A C27A H27C 109.5 . . ? H27B C27A H27C 109.5 . . ? C26A C28A H28A 109.5 . . ? C26A C28A H28B 109.5 . . ? C26A C28A H28C 109.5 . . ? H28A C28A H28B 109.5 . . ? H28A C28A H28C 109.5 . . ? H28B C28A H28C 109.5 . . ? N1 C1B C2B 107.7(4) . . ? C6B C1B N1 129.9(5) . . ? C6B C1B C2B 122.4(5) . . ? C2A C2B C1B 106.9(4) . . ? C2A C2B C3B 133.4(5) . . ? C3B C2B C1B 119.7(5) . . ? C2B C3B H3B 120.7 . . ? C4B C3B C2B 118.5(5) . . ? C4B C3B H3B 120.7 . . ? C3B C4B C5B 122.0(5) . . ? C3B C4B C7B 132.0(5) . . ? C7B C4B C5B 106.0(4) . . ? C6B C5B C4B 119.9(5) . . ? C13B C5B C4B 108.8(5) . . ? C13B C5B C6B 131.3(5) . . ? C1B C6B C5B 117.5(5) . . ? C1B C6B H6B 121.2 . . ? C5B C6B H6B 121.2 . . ? C8B C7B C4B 131.0(5) . . ? C8B C7B C12B 120.8(5) . . ? C12B C7B C4B 108.1(4) . . ? C7B C8B H8B 120.7 . . ? C7B C8B C9B 118.7(5) . . ? C9B C8B H8B 120.7 . . ? C8B C9B H9B 119.7 . . ? C10B C9B C8B 120.6(5) . . ? C10B C9B H9B 119.7 . . ? C9B C10B H10B 119.7 . . ? C9B C10B C11B 120.5(5) . . ? C11B C10B H10B 119.7 . . ? C10B C11B H11B 120.4 . . ? C12B C11B C10B 119.2(5) . . ? C12B C11B H11B 120.4 . . ? C7B C12B C13B 108.0(5) . . ? C11B C12B C7B 120.2(5) . . ? C11B C12B C13B 131.8(5) . . ? C5B C13B C12B 109.1(5) . . ? C5B C13B C14B 127.1(5) . . ? C12B C13B C14B 123.8(5) . . ? C15B C14B C13B 119.4(5) . . ? C19B C14B C13B 120.6(5) . . ? C19B C14B C15B 119.8(5) . . ? C14B C15B C20B 121.2(5) . . ? C16B C15B C14B 118.7(5) . . ? C16B C15B C20B 119.8(5) . . ? C15B C16B H16B 118.4 . . ? C15B C16B C17B 123.2(6) . . ? C17B C16B H16B 118.4 . . ? C16B C17B C18B 116.9(5) . . ? C16B C17B C23B 120.1(6) . . ? C18B C17B C23B 123.0(6) . . ? C17B C18B H18B 118.8 . . ? C17B C18B C19B 122.4(6) . . ? C19B C18B H18B 118.8 . . ? C14B C19B C18B 118.9(5) . . ? C14B C19B C26B 123.4(5) . . ? C18B C19B C26B 117.6(5) . . ? C15B C20B H20B 107.5 . . ? C15B C20B C21B 113.1(5) . . ? C21B C20B H20B 107.5 . . ? C22B C20B C15B 111.0(5) . . ? C22B C20B H20B 107.5 . . ? C22B C20B C21B 109.9(6) . . ? C20B C21B H21D 109.5 . . ? C20B C21B H21E 109.5 . . ? C20B C21B H21F 109.5 . . ? H21D C21B H21E 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? C20B C22B H22D 109.5 . . ? C20B C22B H22E 109.5 . . ? C20B C22B H22F 109.5 . . ? H22D C22B H22E 109.5 . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? C17B C23B H23B 108.5 . . ? C17B C23B C24B 110.6(6) . . ? C17B C23B C25B 113.8(6) . . ? C24B C23B H23B 108.5 . . ? C24B C23B C25B 106.8(6) . . ? C25B C23B H23B 108.5 . . ? C23B C24B H24D 109.5 . . ? C23B C24B H24E 109.5 . . ? C23B C24B H24F 109.5 . . ? H24D C24B H24E 109.5 . . ? H24D C24B H24F 109.5 . . ? H24E C24B H24F 109.5 . . ? C23B C25B H25D 109.5 . . ? C23B C25B H25E 109.5 . . ? C23B C25B H25F 109.5 . . ? H25D C25B H25E 109.5 . . ? H25D C25B H25F 109.5 . . ? H25E C25B H25F 109.5 . . ? C19B C26B H26B 107.4 . . ? C19B C26B C27B 111.8(5) . . ? C19B C26B C28B 111.7(5) . . ? C27B C26B H26B 107.4 . . ? C28B C26B H26B 107.4 . . ? C28B C26B C27B 110.7(5) . . ? C26B C27B H27D 109.5 . . ? C26B C27B H27E 109.5 . . ? C26B C27B H27F 109.5 . . ? H27D C27B H27E 109.5 . . ? H27D C27B H27F 109.5 . . ? H27E C27B H27F 109.5 . . ? C26B C28B H28D 109.5 . . ? C26B C28B H28E 109.5 . . ? C26B C28B H28F 109.5 . . ? H28D C28B H28E 109.5 . . ? H28D C28B H28F 109.5 . . ? H28E C28B H28F 109.5 . . ? N1 C1 H11 108.8 . . ? N1 C1 H12 108.8 . . ? N1 C1 C2 113.7(5) . . ? H11 C1 H12 107.7 . . ? C2 C1 H11 108.8 . . ? C2 C1 H12 108.8 . . ? C1 C2 H21 109.4 . . ? C1 C2 H22 109.4 . . ? C1 C2 C3 111.1(5) . . ? H21 C2 H22 108.0 . . ? C3 C2 H21 109.4 . . ? C3 C2 H22 109.4 . . ? C2 C3 H31 108.8 . . ? C2 C3 H32 108.8 . . ? H31 C3 H32 107.7 . . ? C4 C3 C2 113.8(6) . . ? C4 C3 H31 108.8 . . ? C4 C3 H32 108.8 . . ? C3 C4 H41 109.5 . . ? C3 C4 H42 109.5 . . ? C3 C4 H43 109.5 . . ? H41 C4 H42 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1A 1.392(7) . ? N1 C1B 1.384(7) . ? N1 C1 1.461(6) . ? C1A C2A 1.442(7) . ? C1A C6A 1.378(7) . ? C2A C3A 1.424(7) . ? C2A C2B 1.403(7) . ? C3A H3A 0.9500 . ? C3A C4A 1.358(8) . ? C4A C5A 1.466(7) . ? C4A C7A 1.465(7) . ? C5A C6A 1.415(7) . ? C5A C13A 1.383(8) . ? C6A H6A 0.9500 . ? C7A C8A 1.370(7) . ? C7A C12A 1.413(8) . ? C8A H8A 0.9500 . ? C8A C9A 1.419(8) . ? C9A H9A 0.9500 . ? C9A C10A 1.378(9) . ? C10A H10A 0.9500 . ? C10A C11A 1.392(8) . ? C11A H11A 0.9500 . ? C11A C12A 1.388(8) . ? C12A C13A 1.458(7) . ? C13A C14A 1.498(7) . ? C14A C15A 1.403(8) . ? C14A C19A 1.416(8) . ? C15A C16A 1.401(8) . ? C15A C20A 1.521(9) . ? C16A H16A 0.9500 . ? C16A C17A 1.399(9) . ? C17A C18A 1.387(9) . ? C17A C23A 1.511(8) . ? C18A H18A 0.9500 . ? C18A C19A 1.389(8) . ? C19A C26A 1.508(9) . ? C20A H20A 1.0000 . ? C20A C21A 1.520(11) . ? C20A C22A 1.516(11) . ? C21A H21A 0.9800 . ? C21A H21B 0.9800 . ? C21A H21C 0.9800 . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C23A H23A 1.0000 . ? C23A C24A 1.552(11) . ? C23A C25A 1.514(11) . ? C24A H24A 0.9800 . ? C24A H24B 0.9800 . ? C24A H24C 0.9800 . ? C25A H25A 0.9800 . ? C25A H25B 0.9800 . ? C25A H25C 0.9800 . ? C25C H25G 0.9800 . ? C25C H25H 0.9800 . ? C25C H25I 0.9800 . ? C26A H26A 1.0000 . ? C26A C27A 1.529(9) . ? C26A C28A 1.533(10) . ? C27A H27A 0.9800 . ? C27A H27B 0.9800 . ? C27A H27C 0.9800 . ? C28A H28A 0.9800 . ? C28A H28B 0.9800 . ? C28A H28C 0.9800 . ? C1B C2B 1.453(7) . ? C1B C6B 1.367(8) . ? C2B C3B 1.424(7) . ? C3B H3B 0.9500 . ? C3B C4B 1.338(8) . ? C4B C5B 1.477(7) . ? C4B C7B 1.475(7) . ? C5B C6B 1.416(8) . ? C5B C13B 1.391(8) . ? C6B H6B 0.9500 . ? C7B C8B 1.383(7) . ? C7B C12B 1.422(7) . ? C8B H8B 0.9500 . ? C8B C9B 1.400(8) . ? C9B H9B 0.9500 . ? C9B C10B 1.396(8) . ? C10B H10B 0.9500 . ? C10B C11B 1.404(8) . ? C11B H11B 0.9500 . ? C11B C12B 1.373(8) . ? C12B C13B 1.464(7) . ? C13B C14B 1.491(7) . ? C14B C15B 1.418(8) . ? C14B C19B 1.399(8) . ? C15B C16B 1.389(8) . ? C15B C20B 1.523(8) . ? C16B H16B 0.9500 . ? C16B C17B 1.390(9) . ? C17B C18B 1.400(8) . ? C17B C23B 1.516(8) . ? C18B H18B 0.9500 . ? C18B C19B 1.404(8) . ? C19B C26B 1.517(8) . ? C20B H20B 1.0000 . ? C20B C21B 1.531(8) . ? C20B C22B 1.521(9) . ? C21B H21D 0.9800 . ? C21B H21E 0.9800 . ? C21B H21F 0.9800 . ? C22B H22D 0.9800 . ? C22B H22E 0.9800 . ? C22B H22F 0.9800 . ? C23B H23B 1.0000 . ? C23B C24B 1.528(10) . ? C23B C25B 1.551(11) . ? C24B H24D 0.9800 . ? C24B H24E 0.9800 . ? C24B H24F 0.9800 . ? C25B H25D 0.9800 . ? C25B H25E 0.9800 . ? C25B H25F 0.9800 . ? C26B H26B 1.0000 . ? C26B C27B 1.524(8) . ? C26B C28B 1.521(9) . ? C27B H27D 0.9800 . ? C27B H27E 0.9800 . ? C27B H27F 0.9800 . ? C28B H28D 0.9800 . ? C28B H28E 0.9800 . ? C28B H28F 0.9800 . ? C1 H11 0.9900 . ? C1 H12 0.9900 . ? C1 C2 1.506(8) . ? C2 H21 0.9900 . ? C2 H22 0.9900 . ? C2 C3 1.515(8) . ? C3 H31 0.9900 . ? C3 H32 0.9900 . ? C3 C4 1.504(9) . ? C4 H41 0.9800 . ? C4 H42 0.9800 . ? C4 H43 0.9800 . ?