#------------------------------------------------------------------------------ #$Date: 2019-02-15 03:52:07 +0200 (Fri, 15 Feb 2019) $ #$Revision: 213656 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/81/7058165.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_7058165 loop_ _publ_author_name 'Nar, Ilg\?in' 'Atsay, Arma\(gan' 'Buyruk, Ali' 'Pekbelgin Karao\(glu, Hande' 'Kalkan Burat, Ayfer' 'Hamuryudan, Esin' _publ_section_title ; BODIPY-ortho-Carborane-Tetraphenylethylene Triad: Synthesis, Characterization, and Properties ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C9NJ00177H _journal_year 2019 _chemical_formula_sum 'C47 H37 B F2 N2' _chemical_formula_weight 678.59 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-01-16 deposited with the CCDC. 2019-02-14 downloaded from the CCDC. ; _cell_angle_alpha 80.996(3) _cell_angle_beta 83.209(3) _cell_angle_gamma 76.283(3) _cell_formula_units_Z 2 _cell_length_a 8.4917(9) _cell_length_b 10.9196(11) _cell_length_c 20.148(2) _cell_measurement_reflns_used 9991 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 28.09 _cell_measurement_theta_min 2.31 _cell_volume 1786.2(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 120(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type Bruker_D8_Venture _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0539 _diffrn_reflns_av_unetI/netI 0.0463 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 70562 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.548 _diffrn_reflns_theta_min 1.937 _diffrn_source Sealed_Tube _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.7257 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.262 _exptl_crystal_description block _exptl_crystal_F_000 712 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.603 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 473 _refine_ls_number_reflns 9033 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0596 _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^)+(0.0583P)^2^+1.2729P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1294 _refine_ls_wR_factor_ref 0.1453 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6318 _reflns_number_total 9033 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9nj00177h2.cif _cod_data_source_block 701Armagan_0m_a _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi_Scan' changed to 'multi-scan' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 7058165 _shelx_shelxl_version_number 2014/7 _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_min 0.969 _shelx_estimated_absorpt_t_max 0.998 _shelx_res_file ; 701Armagan_0m_a.res created by SHELXL-2014/7 TITL 701Armagan_0m_a.res in P-1 CELL 0.71073 8.4917 10.9196 20.1484 80.996 83.209 76.283 ZERR 2.000 0.0009 0.0011 0.0021 0.003 0.003 0.003 LATT 1 SFAC C H B F N UNIT 94 74 2 4 4 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 15 BOND $H ACTA FMAP 2 PLAN 20 SIZE 0.03 0.20 0.40 TEMP -153.160 WGHT 0.058300 1.272900 FVAR 0.37053 F001 4 -0.199642 -0.055722 0.490700 11.00000 0.03186 0.02086 = 0.02441 0.00330 0.00056 -0.01091 F002 4 -0.319043 0.030919 0.393788 11.00000 0.02414 0.03447 = 0.03014 -0.00374 -0.00584 -0.01491 N003 5 -0.029960 0.008402 0.393486 11.00000 0.02164 0.01633 = 0.01900 -0.00045 -0.00266 -0.00886 N004 5 -0.225360 0.169016 0.454897 11.00000 0.01638 0.01822 = 0.02262 0.00004 -0.00060 -0.00621 C005 1 0.061946 0.099672 0.370022 11.00000 0.01929 0.01939 = 0.01637 0.00078 -0.00266 -0.00895 C006 1 -0.134040 0.258796 0.427556 11.00000 0.02137 0.01621 = 0.01890 0.00146 -0.00230 -0.00747 C007 1 0.008806 0.222839 0.385776 11.00000 0.02108 0.01826 = 0.01434 0.00146 -0.00503 -0.00774 C008 1 0.113084 0.315492 0.361032 11.00000 0.02029 0.01548 = 0.01994 -0.00207 0.00154 -0.00705 C009 1 1.183003 1.024199 0.094019 11.00000 0.01394 0.01743 = 0.02714 0.00053 0.00156 -0.00225 C00A 1 -0.206408 0.373615 0.454666 11.00000 0.02273 0.01854 = 0.02353 -0.00065 -0.00389 -0.00481 C00B 1 0.928481 0.973423 0.153970 11.00000 0.02039 0.01820 = 0.01811 -0.00057 -0.00110 -0.00656 C00C 1 0.232296 0.324534 0.400468 11.00000 0.03106 0.02345 = 0.01837 0.00105 -0.00297 -0.01404 AFIX 43 H00C 2 0.242797 0.274547 0.443431 11.00000 -1.20000 AFIX 0 C00D 1 0.824360 0.884669 0.186005 11.00000 0.02127 0.01903 = 0.01657 -0.00295 0.00310 -0.00724 C00E 1 0.621111 0.720518 0.244276 11.00000 0.02408 0.01974 = 0.02216 -0.00461 0.00658 -0.01009 C00F 1 0.208562 0.038238 0.334747 11.00000 0.02306 0.02272 = 0.01851 -0.00351 -0.00164 -0.00797 C00G 1 0.657771 0.917648 0.177306 11.00000 0.01809 0.01922 = 0.02345 -0.00223 0.00005 -0.00324 AFIX 43 H00G 2 0.612938 0.996186 0.151539 11.00000 -1.20000 AFIX 0 C00H 1 0.051472 -0.102966 0.374147 11.00000 0.02548 0.01817 = 0.02255 -0.00234 -0.00572 -0.00759 C00I 1 -0.346514 0.223319 0.497504 11.00000 0.01799 0.02492 = 0.02286 -0.00029 -0.00222 -0.00331 C00J 1 1.072303 0.935271 0.117473 11.00000 0.02043 0.01758 = 0.01870 -0.00027 -0.00172 -0.00560 C00K 1 -0.336673 0.348696 0.498902 11.00000 0.02000 0.02148 = 0.02879 -0.00219 0.00127 -0.00219 AFIX 43 H00K 2 -0.407120 0.406996 0.525579 11.00000 -1.20000 AFIX 0 C00L 1 1.130407 0.803676 0.098881 11.00000 0.02635 0.01920 = 0.01784 0.00062 0.00341 -0.00527 C00M 1 0.335910 0.405564 0.377845 11.00000 0.02663 0.02398 = 0.02517 -0.00582 -0.00158 -0.01170 AFIX 43 H00M 2 0.418221 0.409891 0.404928 11.00000 -1.20000 AFIX 0 C00N 1 0.857720 1.108860 0.164101 11.00000 0.01711 0.01991 = 0.02254 -0.00397 0.00181 -0.00652 C00O 1 0.426299 0.566152 0.291822 11.00000 0.02368 0.01801 = 0.02879 -0.00491 0.00631 -0.00600 C00P 1 1.224775 1.094849 0.139127 11.00000 0.02125 0.02451 = 0.02494 0.00102 -0.00164 -0.00717 AFIX 43 H00P 2 1.182257 1.086259 0.184974 11.00000 -1.20000 AFIX 0 C00Q 1 0.786344 0.689870 0.254359 11.00000 0.02675 0.02024 = 0.02421 0.00305 0.00043 -0.00749 AFIX 43 H00Q 2 0.830797 0.612408 0.281112 11.00000 -1.20000 AFIX 0 C00R 1 0.841664 1.206758 0.110227 11.00000 0.02764 0.02182 = 0.02380 -0.00285 0.00399 -0.00435 AFIX 43 H00R 2 0.879927 1.188203 0.065860 11.00000 -1.20000 AFIX 0 C00S 1 0.097408 0.389253 0.298205 11.00000 0.02328 0.02228 = 0.02409 0.00140 -0.00367 -0.00766 AFIX 43 H00S 2 0.016384 0.383244 0.270904 11.00000 -1.20000 AFIX 0 C00T 1 0.886169 0.770749 0.225928 11.00000 0.01930 0.02610 = 0.02309 0.00087 -0.00008 -0.00602 AFIX 43 H00T 2 0.998242 0.748538 0.233652 11.00000 -1.20000 AFIX 0 C00U 1 0.200181 0.471625 0.275424 11.00000 0.02739 0.02001 = 0.02362 0.00429 0.00105 -0.00667 AFIX 43 H00U 2 0.189119 0.521826 0.232538 11.00000 -1.20000 AFIX 0 C00V 1 0.197673 -0.086905 0.337380 11.00000 0.02703 0.02068 = 0.02570 -0.00596 0.00157 -0.00608 AFIX 43 H00V 2 0.276302 -0.151324 0.317544 11.00000 -1.20000 AFIX 0 C00W 1 0.319725 0.481070 0.315222 11.00000 0.02194 0.01589 = 0.02616 -0.00562 0.00676 -0.00743 C00X 1 -0.160700 0.500054 0.439853 11.00000 0.03609 0.01778 = 0.03046 -0.00520 0.00443 -0.00909 AFIX 137 H00A 2 -0.217453 0.554132 0.473735 11.00000 -1.50000 H00B 2 -0.191809 0.540901 0.394984 11.00000 -1.50000 H00D 2 -0.042934 0.487853 0.441148 11.00000 -1.50000 AFIX 0 C00Y 1 1.388457 1.191783 0.049786 11.00000 0.02334 0.02105 = 0.03875 0.00256 0.00445 -0.01064 AFIX 43 H00Y 2 1.456904 1.249643 0.034549 11.00000 -1.20000 AFIX 0 C00Z 1 0.798122 1.138447 0.229009 11.00000 0.02732 0.02732 = 0.02507 -0.00481 0.00289 -0.00898 AFIX 43 H00Z 2 0.805585 1.072140 0.265932 11.00000 -1.20000 AFIX 0 C010 1 -0.009238 -0.223052 0.391865 11.00000 0.03282 0.02016 = 0.02949 -0.00280 -0.00187 -0.01292 AFIX 137 H01A 2 -0.009303 -0.249616 0.440633 11.00000 -1.50000 H01B 2 0.062003 -0.290000 0.368128 11.00000 -1.50000 H01C 2 -0.120137 -0.208115 0.378426 11.00000 -1.50000 AFIX 0 C011 1 0.557783 0.836550 0.206013 11.00000 0.01823 0.02329 = 0.02885 -0.00381 0.00167 -0.00705 AFIX 43 H011 2 0.444950 0.859989 0.199647 11.00000 -1.20000 AFIX 0 C012 1 -0.470602 0.155989 0.534095 11.00000 0.01928 0.02741 = 0.03871 -0.00240 0.00361 -0.00795 AFIX 137 H01D 2 -0.527159 0.128161 0.501506 11.00000 -1.50000 H01E 2 -0.549335 0.213662 0.561065 11.00000 -1.50000 H01F 2 -0.417141 0.081742 0.563846 11.00000 -1.50000 AFIX 0 C013 1 1.247666 1.038053 0.027481 11.00000 0.02334 0.02527 = 0.02667 -0.00469 0.00251 -0.00527 AFIX 43 H013 2 1.222634 0.989579 -0.003478 11.00000 -1.20000 AFIX 0 C014 1 1.327775 1.177112 0.117116 11.00000 0.02597 0.02464 = 0.03460 -0.00272 -0.00334 -0.01087 AFIX 43 H014 2 1.356956 1.223537 0.148071 11.00000 -1.20000 AFIX 0 C015 1 0.728863 1.262000 0.240268 11.00000 0.03140 0.03142 = 0.03156 -0.01569 0.00887 -0.00573 AFIX 43 H015 2 0.691935 1.281246 0.284625 11.00000 -1.20000 AFIX 0 C016 1 0.352595 0.091419 0.304965 11.00000 0.02234 0.02636 = 0.02953 -0.00757 0.00436 -0.00859 AFIX 137 H01G 2 0.403828 0.114191 0.340988 11.00000 -1.50000 H01H 2 0.316869 0.167363 0.272724 11.00000 -1.50000 H01I 2 0.431243 0.027466 0.281713 11.00000 -1.50000 AFIX 0 C017 1 0.516100 0.636072 0.271732 11.00000 0.02485 0.02036 = 0.02820 -0.00622 0.00565 -0.00712 C018 1 1.024919 0.738693 0.078396 11.00000 0.03420 0.02685 = 0.02663 -0.00491 0.00390 -0.01038 AFIX 43 H018 2 0.913996 0.780011 0.074355 11.00000 -1.20000 AFIX 0 C019 1 1.349247 1.122594 0.005544 11.00000 0.02561 0.03159 = 0.02821 0.00206 0.00726 -0.00872 AFIX 43 H019 2 1.391388 1.132162 -0.040328 11.00000 -1.20000 AFIX 0 C01A 1 1.293353 0.740822 0.101093 11.00000 0.02822 0.03023 = 0.02967 -0.00101 0.00212 0.00064 AFIX 43 H01J 2 1.369015 0.783758 0.112859 11.00000 -1.20000 AFIX 0 C01B 1 0.770782 1.330249 0.120726 11.00000 0.04125 0.02345 = 0.03558 -0.00064 0.00269 -0.00040 AFIX 43 H01K 2 0.760847 1.396241 0.083631 11.00000 -1.20000 AFIX 0 C01C 1 0.713935 1.358577 0.185161 11.00000 0.04191 0.02228 = 0.04349 -0.01175 0.00449 0.00171 AFIX 43 H01L 2 0.664638 1.443824 0.192005 11.00000 -1.20000 AFIX 0 B01D 3 -0.197577 0.033853 0.434008 11.00000 0.02092 0.01848 = 0.01996 0.00124 -0.00250 -0.00962 C01E 1 1.079579 0.615379 0.063956 11.00000 0.06204 0.02865 = 0.03756 -0.01271 0.01076 -0.02019 AFIX 43 H01M 2 1.005589 0.572448 0.050816 11.00000 -1.20000 AFIX 0 C01F 1 1.239906 0.554233 0.068417 11.00000 0.07345 0.02000 = 0.04168 -0.00698 0.01362 -0.00346 AFIX 43 H01N 2 1.276362 0.468980 0.059059 11.00000 -1.20000 AFIX 0 C01G 1 1.347469 0.617180 0.086524 11.00000 0.04502 0.03390 = 0.03998 -0.00118 0.00752 0.01038 AFIX 43 H01O 2 1.458834 0.575805 0.089028 11.00000 -1.20000 AFIX 0 HKLF 4 REM 701Armagan_0m_a.res in P-1 REM R1 = 0.0596 for 6318 Fo > 4sig(Fo) and 0.0977 for all 9033 data REM 473 parameters refined using 0 restraints END WGHT 0.0588 1.2624 REM Highest difference peak 0.603, deepest hole -0.265, 1-sigma level 0.058 Q1 1 0.8325 1.4487 0.1543 11.00000 0.05 0.60 Q2 1 0.7011 1.2603 0.1168 11.00000 0.05 0.49 Q3 1 0.0908 -0.0329 0.3218 11.00000 0.05 0.42 Q4 1 1.1571 1.0117 0.0503 11.00000 0.05 0.38 Q5 1 0.0706 0.3306 0.2697 11.00000 0.05 0.37 Q6 1 0.6881 0.7348 0.2703 11.00000 0.05 0.36 Q7 1 1.1575 1.1253 0.1706 11.00000 0.05 0.36 Q8 1 -0.2508 0.2651 0.4017 11.00000 0.05 0.35 Q9 1 0.0815 -0.2836 0.3802 11.00000 0.05 0.34 Q10 1 1.3205 1.2145 0.0186 11.00000 0.05 0.32 Q11 1 0.3577 0.1923 0.3368 11.00000 0.05 0.31 Q12 1 -0.3318 0.3758 0.5341 11.00000 0.05 0.30 Q13 1 1.4391 0.4990 0.0344 11.00000 0.05 0.29 Q14 1 -0.0904 0.5082 0.4056 11.00000 0.05 0.29 Q15 1 -0.1481 0.3231 0.4409 11.00000 0.05 0.27 Q16 1 -0.3070 0.3762 0.4688 11.00000 0.05 0.24 Q17 1 0.9733 0.8507 0.2184 11.00000 0.05 0.24 Q18 1 0.6526 1.3012 0.2127 11.00000 0.05 0.24 Q19 1 0.0141 -0.1592 0.3792 11.00000 0.05 0.24 Q20 1 1.1190 0.4867 0.1030 11.00000 0.05 0.23 ; _shelx_res_checksum 84207 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 F001 F -0.19964(14) -0.05572(10) 0.49070(5) 0.0258(3) Uani 1 1 d . . F002 F -0.31904(13) 0.03092(11) 0.39379(6) 0.0279(3) Uani 1 1 d . . N003 N -0.02996(18) 0.00840(14) 0.39349(7) 0.0183(3) Uani 1 1 d . . N004 N -0.22536(18) 0.16902(14) 0.45490(8) 0.0191(3) Uani 1 1 d . . C005 C 0.0619(2) 0.09967(16) 0.37002(9) 0.0178(4) Uani 1 1 d . . C006 C -0.1340(2) 0.25880(16) 0.42756(9) 0.0186(4) Uani 1 1 d . . C007 C 0.0088(2) 0.22284(16) 0.38578(9) 0.0174(4) Uani 1 1 d . . C008 C 0.1131(2) 0.31549(16) 0.36103(9) 0.0183(4) Uani 1 1 d . . C009 C 1.1830(2) 1.02420(17) 0.09402(10) 0.0204(4) Uani 1 1 d . . C00A C -0.2064(2) 0.37362(17) 0.45467(9) 0.0216(4) Uani 1 1 d . . C00B C 0.9285(2) 0.97342(16) 0.15397(9) 0.0188(4) Uani 1 1 d . . C00C C 0.2323(2) 0.32453(18) 0.40047(9) 0.0233(4) Uani 1 1 d . . H00C H 0.2428 0.2745 0.4434 0.028 Uiso 1 1 calc R U C00D C 0.8244(2) 0.88467(17) 0.18600(9) 0.0188(4) Uani 1 1 d . . C00E C 0.6211(2) 0.72052(17) 0.24428(9) 0.0216(4) Uani 1 1 d . . C00F C 0.2086(2) 0.03824(17) 0.33475(9) 0.0209(4) Uani 1 1 d . . C00G C 0.6578(2) 0.91765(17) 0.17731(9) 0.0206(4) Uani 1 1 d . . H00G H 0.6129 0.9962 0.1515 0.025 Uiso 1 1 calc R U C00H C 0.0515(2) -0.10297(17) 0.37415(9) 0.0213(4) Uani 1 1 d . . C00I C -0.3465(2) 0.22332(18) 0.49750(9) 0.0225(4) Uani 1 1 d . . C00J C 1.0723(2) 0.93527(16) 0.11747(9) 0.0189(4) Uani 1 1 d . . C00K C -0.3367(2) 0.34870(18) 0.49890(10) 0.0242(4) Uani 1 1 d . . H00K H -0.4071 0.4070 0.5256 0.029 Uiso 1 1 calc R U C00L C 1.1304(2) 0.80368(17) 0.09888(9) 0.0219(4) Uani 1 1 d . . C00M C 0.3359(2) 0.40556(18) 0.37784(10) 0.0240(4) Uani 1 1 d . . H00M H 0.4182 0.4099 0.4049 0.029 Uiso 1 1 calc R U C00N C 0.8577(2) 1.10886(17) 0.16410(9) 0.0196(4) Uani 1 1 d . . C00O C 0.4263(2) 0.56615(17) 0.29182(10) 0.0238(4) Uani 1 1 d . . C00P C 1.2248(2) 1.09485(18) 0.13913(10) 0.0237(4) Uani 1 1 d . . H00P H 1.1823 1.0863 0.1850 0.028 Uiso 1 1 calc R U C00Q C 0.7863(2) 0.68987(18) 0.25436(10) 0.0242(4) Uani 1 1 d . . H00Q H 0.8308 0.6124 0.2811 0.029 Uiso 1 1 calc R U C00R C 0.8417(2) 1.20676(18) 0.11023(10) 0.0251(4) Uani 1 1 d . . H00R H 0.8799 1.1882 0.0659 0.030 Uiso 1 1 calc R U C00S C 0.0974(2) 0.38925(17) 0.29821(10) 0.0231(4) Uani 1 1 d . . H00S H 0.0164 0.3832 0.2709 0.028 Uiso 1 1 calc R U C00T C 0.8862(2) 0.77075(18) 0.22593(9) 0.0233(4) Uani 1 1 d . . H00T H 0.9982 0.7485 0.2337 0.028 Uiso 1 1 calc R U C00U C 0.2002(2) 0.47163(18) 0.27542(10) 0.0245(4) Uani 1 1 d . . H00U H 0.1891 0.5218 0.2325 0.029 Uiso 1 1 calc R U C00V C 0.1977(2) -0.08690(18) 0.33738(10) 0.0243(4) Uani 1 1 d . . H00V H 0.2763 -0.1513 0.3175 0.029 Uiso 1 1 calc R U C00W C 0.3197(2) 0.48107(16) 0.31522(10) 0.0212(4) Uani 1 1 d . . C00X C -0.1607(3) 0.50005(18) 0.43985(11) 0.0280(4) Uani 1 1 d . . H00A H -0.2175 0.5541 0.4737 0.042 Uiso 1 1 calc R U H00B H -0.1918 0.5409 0.3950 0.042 Uiso 1 1 calc R U H00D H -0.0429 0.4879 0.4411 0.042 Uiso 1 1 calc R U C00Y C 1.3885(2) 1.19178(18) 0.04979(11) 0.0281(4) Uani 1 1 d . . H00Y H 1.4569 1.2496 0.0345 0.034 Uiso 1 1 calc R U C00Z C 0.7981(2) 1.13845(19) 0.22901(10) 0.0264(4) Uani 1 1 d . . H00Z H 0.8056 1.0721 0.2659 0.032 Uiso 1 1 calc R U C010 C -0.0092(3) -0.22305(18) 0.39186(10) 0.0264(4) Uani 1 1 d . . H01A H -0.0093 -0.2496 0.4406 0.040 Uiso 1 1 calc R U H01B H 0.0620 -0.2900 0.3681 0.040 Uiso 1 1 calc R U H01C H -0.1201 -0.2081 0.3784 0.040 Uiso 1 1 calc R U C011 C 0.5578(2) 0.83655(18) 0.20601(10) 0.0233(4) Uani 1 1 d . . H011 H 0.4449 0.8600 0.1996 0.028 Uiso 1 1 calc R U C012 C -0.4706(2) 0.15599(19) 0.53410(11) 0.0287(4) Uani 1 1 d . . H01D H -0.5272 0.1282 0.5015 0.043 Uiso 1 1 calc R U H01E H -0.5493 0.2137 0.5611 0.043 Uiso 1 1 calc R U H01F H -0.4171 0.0817 0.5638 0.043 Uiso 1 1 calc R U C013 C 1.2477(2) 1.03805(18) 0.02748(10) 0.0254(4) Uani 1 1 d . . H013 H 1.2226 0.9896 -0.0035 0.030 Uiso 1 1 calc R U C014 C 1.3278(2) 1.17711(18) 0.11712(11) 0.0276(4) Uani 1 1 d . . H014 H 1.3570 1.2235 0.1481 0.033 Uiso 1 1 calc R U C015 C 0.7289(3) 1.2620(2) 0.24027(11) 0.0314(5) Uani 1 1 d . . H015 H 0.6919 1.2812 0.2846 0.038 Uiso 1 1 calc R U C016 C 0.3526(2) 0.09142(19) 0.30496(10) 0.0257(4) Uani 1 1 d . . H01G H 0.4038 0.1142 0.3410 0.038 Uiso 1 1 calc R U H01H H 0.3169 0.1674 0.2727 0.038 Uiso 1 1 calc R U H01I H 0.4312 0.0275 0.2817 0.038 Uiso 1 1 calc R U C017 C 0.5161(2) 0.63607(18) 0.27173(10) 0.0244(4) Uani 1 1 d . . C018 C 1.0249(3) 0.73869(19) 0.07840(10) 0.0290(4) Uani 1 1 d . . H018 H 0.9140 0.7800 0.0744 0.035 Uiso 1 1 calc R U C019 C 1.3492(2) 1.12259(19) 0.00554(11) 0.0295(5) Uani 1 1 d . . H019 H 1.3914 1.1322 -0.0403 0.035 Uiso 1 1 calc R U C01A C 1.2934(3) 0.7408(2) 0.10109(11) 0.0313(5) Uani 1 1 d . . H01J H 1.3690 0.7838 0.1129 0.038 Uiso 1 1 calc R U C01B C 0.7708(3) 1.3302(2) 0.12073(12) 0.0354(5) Uani 1 1 d . . H01K H 0.7608 1.3962 0.0836 0.043 Uiso 1 1 calc R U C01C C 0.7139(3) 1.3586(2) 0.18516(12) 0.0373(5) Uani 1 1 d . . H01L H 0.6646 1.4438 0.1920 0.045 Uiso 1 1 calc R U B01D B -0.1976(3) 0.03385(19) 0.43401(10) 0.0193(4) Uani 1 1 d . . C01E C 1.0796(3) 0.6154(2) 0.06396(12) 0.0414(6) Uani 1 1 d . . H01M H 1.0056 0.5724 0.0508 0.050 Uiso 1 1 calc R U C01F C 1.2399(4) 0.5542(2) 0.06842(13) 0.0474(7) Uani 1 1 d . . H01N H 1.2764 0.4690 0.0591 0.057 Uiso 1 1 calc R U C01G C 1.3475(3) 0.6172(2) 0.08652(12) 0.0442(6) Uani 1 1 d . . H01O H 1.4588 0.5758 0.0890 0.053 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 F001 0.0319(6) 0.0209(5) 0.0244(6) 0.0033(4) 0.0006(5) -0.0109(5) F002 0.0241(6) 0.0345(6) 0.0301(6) -0.0037(5) -0.0058(5) -0.0149(5) N003 0.0216(8) 0.0163(7) 0.0190(8) -0.0004(6) -0.0027(6) -0.0089(6) N004 0.0164(7) 0.0182(7) 0.0226(8) 0.0000(6) -0.0006(6) -0.0062(6) C005 0.0193(9) 0.0194(8) 0.0164(8) 0.0008(7) -0.0027(7) -0.0089(7) C006 0.0214(9) 0.0162(8) 0.0189(9) 0.0015(7) -0.0023(7) -0.0075(7) C007 0.0211(9) 0.0183(8) 0.0143(8) 0.0015(7) -0.0050(7) -0.0077(7) C008 0.0203(9) 0.0155(8) 0.0199(9) -0.0021(7) 0.0015(7) -0.0071(7) C009 0.0139(8) 0.0174(8) 0.0271(10) 0.0005(7) 0.0016(7) -0.0023(7) C00A 0.0227(9) 0.0185(9) 0.0235(9) -0.0007(7) -0.0039(7) -0.0048(7) C00B 0.0204(9) 0.0182(8) 0.0181(9) -0.0006(7) -0.0011(7) -0.0066(7) C00C 0.0311(10) 0.0234(9) 0.0184(9) 0.0011(7) -0.0030(8) -0.0140(8) C00D 0.0213(9) 0.0190(8) 0.0166(9) -0.0030(7) 0.0031(7) -0.0072(7) C00E 0.0241(9) 0.0197(9) 0.0222(9) -0.0046(7) 0.0066(7) -0.0101(8) C00F 0.0231(9) 0.0227(9) 0.0185(9) -0.0035(7) -0.0016(7) -0.0080(8) C00G 0.0181(9) 0.0192(9) 0.0234(9) -0.0022(7) 0.0001(7) -0.0032(7) C00H 0.0255(10) 0.0182(9) 0.0225(9) -0.0023(7) -0.0057(8) -0.0076(7) C00I 0.0180(9) 0.0249(9) 0.0229(9) -0.0003(8) -0.0022(7) -0.0033(8) C00J 0.0204(9) 0.0176(8) 0.0187(9) -0.0003(7) -0.0017(7) -0.0056(7) C00K 0.0200(9) 0.0215(9) 0.0288(10) -0.0022(8) 0.0013(8) -0.0022(8) C00L 0.0264(10) 0.0192(9) 0.0178(9) 0.0006(7) 0.0034(7) -0.0053(8) C00M 0.0266(10) 0.0240(9) 0.0252(10) -0.0058(8) -0.0016(8) -0.0117(8) C00N 0.0171(9) 0.0199(9) 0.0225(9) -0.0040(7) 0.0018(7) -0.0065(7) C00O 0.0237(10) 0.0180(9) 0.0288(10) -0.0049(8) 0.0063(8) -0.0060(8) C00P 0.0212(9) 0.0245(9) 0.0249(10) 0.0010(8) -0.0016(8) -0.0072(8) C00Q 0.0268(10) 0.0202(9) 0.0242(10) 0.0030(7) 0.0004(8) -0.0075(8) C00R 0.0276(10) 0.0218(9) 0.0238(10) -0.0028(8) 0.0040(8) -0.0043(8) C00S 0.0233(9) 0.0223(9) 0.0241(10) 0.0014(8) -0.0037(8) -0.0077(8) C00T 0.0193(9) 0.0261(10) 0.0231(10) 0.0009(8) -0.0001(7) -0.0060(8) C00U 0.0274(10) 0.0200(9) 0.0236(10) 0.0043(7) 0.0011(8) -0.0067(8) C00V 0.0270(10) 0.0207(9) 0.0257(10) -0.0060(8) 0.0016(8) -0.0061(8) C00W 0.0219(9) 0.0159(8) 0.0262(10) -0.0056(7) 0.0068(7) -0.0074(7) C00X 0.0361(11) 0.0178(9) 0.0305(11) -0.0052(8) 0.0044(9) -0.0091(8) C00Y 0.0233(10) 0.0210(9) 0.0388(12) 0.0026(8) 0.0045(9) -0.0106(8) C00Z 0.0273(10) 0.0273(10) 0.0251(10) -0.0048(8) 0.0029(8) -0.0090(8) C010 0.0328(11) 0.0202(9) 0.0295(10) -0.0028(8) -0.0019(8) -0.0129(8) C011 0.0182(9) 0.0233(9) 0.0288(10) -0.0038(8) 0.0017(8) -0.0071(8) C012 0.0193(10) 0.0274(10) 0.0387(12) -0.0024(9) 0.0036(8) -0.0080(8) C013 0.0233(10) 0.0253(10) 0.0267(10) -0.0047(8) 0.0025(8) -0.0053(8) C014 0.0260(10) 0.0246(10) 0.0346(11) -0.0027(8) -0.0033(8) -0.0109(8) C015 0.0314(11) 0.0314(11) 0.0316(11) -0.0157(9) 0.0089(9) -0.0057(9) C016 0.0223(10) 0.0264(10) 0.0295(10) -0.0076(8) 0.0044(8) -0.0086(8) C017 0.0248(10) 0.0204(9) 0.0282(10) -0.0062(8) 0.0057(8) -0.0071(8) C018 0.0342(11) 0.0269(10) 0.0266(10) -0.0049(8) 0.0039(9) -0.0104(9) C019 0.0256(10) 0.0316(11) 0.0282(11) 0.0021(9) 0.0073(8) -0.0087(9) C01A 0.0282(11) 0.0302(11) 0.0297(11) -0.0010(9) 0.0021(9) 0.0006(9) C01B 0.0413(13) 0.0235(10) 0.0356(12) -0.0006(9) 0.0027(10) -0.0004(9) C01C 0.0419(13) 0.0223(10) 0.0435(13) -0.0118(9) 0.0045(10) 0.0017(9) B01D 0.0209(10) 0.0185(9) 0.0200(10) 0.0012(8) -0.0025(8) -0.0096(8) C01E 0.0620(17) 0.0287(11) 0.0376(13) -0.0127(10) 0.0108(11) -0.0202(12) C01F 0.0735(19) 0.0200(10) 0.0417(14) -0.0070(10) 0.0136(13) -0.0035(12) C01G 0.0450(14) 0.0339(12) 0.0400(13) -0.0012(10) 0.0075(11) 0.0104(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 C00H N003 C005 108.50(15) C00H N003 B01D 126.34(15) C005 N003 B01D 125.15(14) C00I N004 C006 108.38(15) C00I N004 B01D 126.66(15) C006 N004 B01D 124.77(15) C007 C005 N003 120.47(16) C007 C005 C00F 131.62(16) N003 C005 C00F 107.80(15) N004 C006 C007 119.87(15) N004 C006 C00A 107.74(15) C007 C006 C00A 132.19(16) C005 C007 C006 121.58(15) C005 C007 C008 118.37(16) C006 C007 C008 119.92(15) C00C C008 C00S 119.58(16) C00C C008 C007 119.08(16) C00S C008 C007 121.29(16) C013 C009 C00P 118.56(17) C013 C009 C00J 120.82(17) C00P C009 C00J 120.61(16) C00K C00A C006 106.25(16) C00K C00A C00X 124.35(17) C006 C00A C00X 129.38(17) C00J C00B C00D 123.10(16) C00J C00B C00N 123.26(16) C00D C00B C00N 113.62(15) C00M C00C C008 120.68(17) C00M C00C H00C 119.7 C008 C00C H00C 119.7 C00T C00D C00G 118.62(16) C00T C00D C00B 122.30(16) C00G C00D C00B 119.07(16) C00Q C00E C011 118.49(16) C00Q C00E C017 121.73(17) C011 C00E C017 119.77(17) C00V C00F C005 105.73(16) C00V C00F C016 125.35(17) C005 C00F C016 128.77(16) C011 C00G C00D 120.46(17) C011 C00G H00G 119.8 C00D C00G H00G 119.8 N003 C00H C00V 109.18(16) N003 C00H C010 123.17(17) C00V C00H C010 127.64(17) N004 C00I C00K 109.27(16) N004 C00I C012 122.89(17) C00K C00I C012 127.81(18) C00B C00J C009 121.06(16) C00B C00J C00L 122.91(16) C009 C00J C00L 116.03(15) C00A C00K C00I 108.34(17) C00A C00K H00K 125.8 C00I C00K H00K 125.8 C01A C00L C018 117.19(18) C01A C00L C00J 120.95(18) C018 C00L C00J 121.86(17) C00C C00M C00W 120.11(18) C00C C00M H00M 119.9 C00W C00M H00M 119.9 C00R C00N C00Z 118.60(17) C00R C00N C00B 121.81(16) C00Z C00N C00B 119.51(16) C017 C00O C00W 179.2(2) C014 C00P C009 120.38(18) C014 C00P H00P 119.8 C009 C00P H00P 119.8 C00T C00Q C00E 120.83(17) C00T C00Q H00Q 119.6 C00E C00Q H00Q 119.6 C01B C00R C00N 120.60(18) C01B C00R H00R 119.7 C00N C00R H00R 119.7 C00U C00S C008 120.04(18) C00U C00S H00S 120.0 C008 C00S H00S 120.0 C00Q C00T C00D 120.79(17) C00Q C00T H00T 119.6 C00D C00T H00T 119.6 C00S C00U C00W 120.38(17) C00S C00U H00U 119.8 C00W C00U H00U 119.8 C00F C00V C00H 108.76(17) C00F C00V H00V 125.6 C00H C00V H00V 125.6 C00U C00W C00M 119.20(16) C00U C00W C00O 120.55(17) C00M C00W C00O 120.25(18) C00A C00X H00A 109.5 C00A C00X H00B 109.5 H00A C00X H00B 109.5 C00A C00X H00D 109.5 H00A C00X H00D 109.5 H00B C00X H00D 109.5 C019 C00Y C014 119.84(18) C019 C00Y H00Y 120.1 C014 C00Y H00Y 120.1 C015 C00Z C00N 121.30(19) C015 C00Z H00Z 119.3 C00N C00Z H00Z 119.3 C00H C010 H01A 109.5 C00H C010 H01B 109.5 H01A C010 H01B 109.5 C00H C010 H01C 109.5 H01A C010 H01C 109.5 H01B C010 H01C 109.5 C00G C011 C00E 120.75(17) C00G C011 H011 119.6 C00E C011 H011 119.6 C00I C012 H01D 109.5 C00I C012 H01E 109.5 H01D C012 H01E 109.5 C00I C012 H01F 109.5 H01D C012 H01F 109.5 H01E C012 H01F 109.5 C009 C013 C019 120.64(19) C009 C013 H013 119.7 C019 C013 H013 119.7 C00P C014 C00Y 120.16(19) C00P C014 H014 119.9 C00Y C014 H014 119.9 C00Z C015 C01C 118.89(19) C00Z C015 H015 120.6 C01C C015 H015 120.6 C00F C016 H01G 109.5 C00F C016 H01H 109.5 H01G C016 H01H 109.5 C00F C016 H01I 109.5 H01G C016 H01I 109.5 H01H C016 H01I 109.5 C00O C017 C00E 177.1(2) C01E C018 C00L 121.0(2) C01E C018 H018 119.5 C00L C018 H018 119.5 C00Y C019 C013 120.39(19) C00Y C019 H019 119.8 C013 C019 H019 119.8 C01G C01A C00L 121.5(2) C01G C01A H01J 119.3 C00L C01A H01J 119.3 C00R C01B C01C 120.3(2) C00R C01B H01K 119.9 C01C C01B H01K 119.9 C01B C01C C015 120.29(19) C01B C01C H01L 119.9 C015 C01C H01L 119.9 F001 B01D F002 109.88(15) F001 B01D N003 110.44(15) F002 B01D N003 110.08(15) F001 B01D N004 110.21(15) F002 B01D N004 109.47(15) N003 B01D N004 106.71(14) C01F C01E C018 120.6(2) C01F C01E H01M 119.7 C018 C01E H01M 119.7 C01E C01F C01G 119.6(2) C01E C01F H01N 120.2 C01G C01F H01N 120.2 C01F C01G C01A 120.0(2) C01F C01G H01O 120.0 C01A C01G H01O 120.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F001 B01D 1.384(2) F002 B01D 1.394(2) N003 C00H 1.340(2) N003 C005 1.400(2) N003 B01D 1.542(3) N004 C00I 1.345(2) N004 C006 1.399(2) N004 B01D 1.555(2) C005 C007 1.388(2) C005 C00F 1.431(3) C006 C007 1.404(3) C006 C00A 1.420(3) C007 C008 1.490(2) C008 C00C 1.389(3) C008 C00S 1.392(3) C009 C013 1.387(3) C009 C00P 1.404(3) C009 C00J 1.495(2) C00A C00K 1.388(3) C00A C00X 1.498(3) C00B C00J 1.359(3) C00B C00D 1.488(2) C00B C00N 1.495(2) C00C C00M 1.383(3) C00C H00C 0.9500 C00D C00T 1.395(3) C00D C00G 1.400(3) C00E C00Q 1.395(3) C00E C011 1.399(3) C00E C017 1.437(2) C00F C00V 1.384(3) C00F C016 1.499(3) C00G C011 1.386(3) C00G H00G 0.9500 C00H C00V 1.402(3) C00H C010 1.498(2) C00I C00K 1.396(3) C00I C012 1.486(3) C00J C00L 1.496(2) C00K H00K 0.9500 C00L C01A 1.394(3) C00L C018 1.399(3) C00M C00W 1.397(3) C00M H00M 0.9500 C00N C00R 1.394(3) C00N C00Z 1.403(3) C00O C017 1.198(3) C00O C00W 1.437(2) C00P C014 1.387(3) C00P H00P 0.9500 C00Q C00T 1.382(3) C00Q H00Q 0.9500 C00R C01B 1.378(3) C00R H00R 0.9500 C00S C00U 1.389(3) C00S H00S 0.9500 C00T H00T 0.9500 C00U C00W 1.397(3) C00U H00U 0.9500 C00V H00V 0.9500 C00X H00A 0.9800 C00X H00B 0.9800 C00X H00D 0.9800 C00Y C019 1.370(3) C00Y C014 1.392(3) C00Y H00Y 0.9500 C00Z C015 1.380(3) C00Z H00Z 0.9500 C010 H01A 0.9800 C010 H01B 0.9800 C010 H01C 0.9800 C011 H011 0.9500 C012 H01D 0.9800 C012 H01E 0.9800 C012 H01F 0.9800 C013 C019 1.397(3) C013 H013 0.9500 C014 H014 0.9500 C015 C01C 1.402(3) C015 H015 0.9500 C016 H01G 0.9800 C016 H01H 0.9800 C016 H01I 0.9800 C018 C01E 1.381(3) C018 H018 0.9500 C019 H019 0.9500 C01A C01G 1.385(3) C01A H01J 0.9500 C01B C01C 1.386(3) C01B H01K 0.9500 C01C H01L 0.9500 C01E C01F 1.373(4) C01E H01M 0.9500 C01F C01G 1.377(4) C01F H01N 0.9500 C01G H01O 0.9500