#------------------------------------------------------------------------------ #$Date: 2024-11-13 00:36:27 +0200 (Wed, 13 Nov 2024) $ #$Revision: 295881 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/30/1573093.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_1573093 loop_ _publ_author_name 'Kardela, Marlena' 'Dziuk, B\/la\.zej' 'Szostak, Roman' 'Szostak, Michal' 'Bisz, Elwira' _publ_section_title ; IBzH (IBenzhydryl): Sterically-Flexible N-Aliphatic N-Heterocyclic Carbenes (NHC) for Iron-Catalyzed C(sp3)--C(sp2) Cross-Coupling of Unactivated Haloalkanes ; _journal_name_full 'Catalysis Science & Technology' _journal_paper_doi 10.1039/D4CY01315H _journal_year 2024 _chemical_formula_moiety 'C29 H24 Ag Cl N2' _chemical_formula_sum 'C29 H24 Ag Cl N2' _chemical_formula_weight 543.82 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2024-10-23 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2024-10-23 deposited with the CCDC. 2024-11-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.317(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.0868(11) _cell_length_b 15.0378(14) _cell_length_c 12.4442(9) _cell_measurement_reflns_used 4664 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.000 _cell_measurement_theta_min 2.063 _cell_volume 2448.3(4) _computing_cell_refinement 'CrysAlisCCD (Oxford Diffraction Ltd., 2008)' _computing_data_collection 'CrysAlisCCD (Oxford Diffraction Ltd., 2008)' _computing_data_reduction 'CrysAlisCCD (Oxford Diffraction Ltd., 2008)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2014/7 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'KM4 with Eos CCD' _diffrn_measurement_method \w--scan _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_unetI/netI 0.0471 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 4664 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.000 _diffrn_reflns_theta_min 2.063 _exptl_absorpt_coefficient_mu 0.952 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.75211 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015). ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.282 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.056 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 151 _refine_ls_number_reflns 2408 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0462 _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^)+(0.0284P)^2^+1.0620P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0758 _refine_ls_wR_factor_ref 0.0829 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1716 _reflns_number_total 2408 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4cy01315h2.cif _cod_data_source_block b125_1_a _cod_database_code 1573093 _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. ; _exptl_absorpt_special_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET) (compiled Apr 11 2014,15:12:41) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Ternary CH refined with riding coordinates: C3(H3) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C6(H6), C5(H5), C9(H9), C8(H8), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15) ; _shelx_res_file ; b125_1_a.res created by SHELXL-2014/7 TITL B125_1_a.res in C2/c REM Old TITL B125_1 in Cc REM SHELXT solution in C2/c REM R1 0.173, Rweak 0.420, Alpha 0.062, Orientation as input REM Formula found by SHELXT: C28 N3 Ag Cl CELL 0.71073 13.0868 15.0378 12.4442 90 91.317 90 ZERR 4 0.0011 0.0014 0.0009 0 0.007 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N Ag Cl UNIT 116 96 8 4 4 L.S. 10 PLAN 2 CONF HTAB BOND $H LIST 4 fmap 2 acta MORE -1 OMIT 0 52 REM REM REM WGHT 0.028400 1.062000 FVAR 0.26088 AG1 4 0.500000 0.360228 0.750000 10.50000 0.05950 0.08218 = 0.05157 0.00000 0.00784 0.00000 CL1 5 0.500000 0.513606 0.750000 10.50000 0.15026 0.08495 = 0.09794 0.00000 0.05690 0.00000 N1 3 0.525481 0.167661 0.668834 11.00000 0.06864 0.07816 = 0.03406 -0.00047 0.00236 -0.00436 C1 1 0.500000 0.222839 0.750000 10.50000 0.05325 0.08370 = 0.03679 0.00000 -0.00248 0.00000 C2 1 0.515669 0.079675 0.698678 11.00000 0.09521 0.07931 = 0.04260 -0.00183 0.00307 -0.00122 AFIX 43 H2 2 0.528204 0.030077 0.656329 11.00000 -1.20000 AFIX 0 C3 1 0.552272 0.200472 0.560942 11.00000 0.06165 0.08322 = 0.03925 0.00028 0.00359 -0.01661 AFIX 13 H3 2 0.578368 0.261118 0.570416 11.00000 -1.20000 AFIX 0 C6 1 0.804069 0.078492 0.547552 11.00000 0.06435 0.12730 = 0.16118 -0.00955 0.01779 -0.02203 AFIX 43 H6 2 0.858821 0.065862 0.594025 11.00000 -1.20000 AFIX 0 C5 1 0.722768 0.125890 0.583240 11.00000 0.06200 0.11593 = 0.09409 -0.01864 -0.00144 -0.01219 AFIX 43 H5 2 0.723468 0.145860 0.653984 11.00000 -1.20000 AFIX 0 C4 1 0.639486 0.145035 0.517268 11.00000 0.05625 0.08996 = 0.05755 -0.01069 0.01231 -0.02168 C9 1 0.640809 0.116248 0.412550 11.00000 0.07851 0.12767 = 0.06115 -0.01924 0.02337 -0.02569 AFIX 43 H9 2 0.585940 0.128549 0.366097 11.00000 -1.20000 AFIX 0 C8 1 0.725078 0.068240 0.375737 11.00000 0.11864 0.14355 = 0.09986 -0.02994 0.06262 -0.02772 AFIX 43 H8 2 0.726264 0.049101 0.304712 11.00000 -1.20000 AFIX 0 C7 1 0.805087 0.049679 0.443957 11.00000 0.07958 0.11320 = 0.18533 -0.00055 0.06754 -0.01649 AFIX 43 H7 2 0.860506 0.017259 0.419697 11.00000 -1.20000 AFIX 0 C10 1 0.458580 0.206672 0.487570 11.00000 0.05943 0.10351 = 0.03369 0.00608 0.00704 -0.01710 C11 1 0.383282 0.143201 0.483373 11.00000 0.07833 0.12435 = 0.05644 0.02604 -0.00926 -0.03437 AFIX 43 H11 2 0.388108 0.093857 0.528254 11.00000 -1.20000 AFIX 0 C12 1 0.300770 0.151585 0.413677 11.00000 0.08461 0.15393 = 0.07656 0.03736 -0.01391 -0.05708 AFIX 43 H12 2 0.250508 0.107862 0.411480 11.00000 -1.20000 AFIX 0 C13 1 0.292458 0.223299 0.348228 11.00000 0.07318 0.16237 = 0.07738 0.03827 -0.02214 -0.03427 AFIX 43 H13 2 0.236527 0.228687 0.301217 11.00000 -1.20000 AFIX 0 C14 1 0.365900 0.287616 0.351103 11.00000 0.08977 0.14560 = 0.09132 0.05092 -0.02398 -0.03913 AFIX 43 H14 2 0.360397 0.336717 0.305902 11.00000 -1.20000 AFIX 0 C15 1 0.448624 0.279460 0.421586 11.00000 0.07205 0.12702 = 0.07111 0.02746 -0.01394 -0.03873 AFIX 43 H15 2 0.498116 0.323834 0.424312 11.00000 -1.20000 AFIX 0 HKLF 4 REM B125_1_a.res in C2/c REM R1 = 0.0462 for 1716 Fo > 4sig(Fo) and 0.0761 for all 2408 data REM 151 parameters refined using 0 restraints END WGHT 0.0284 1.0620 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.282, deepest hole -0.373, 1-sigma level 0.056 Q1 1 0.5000 0.5418 0.7500 10.50000 0.05 0.28 Q2 1 0.5313 0.3194 0.8207 11.00000 0.05 0.25 ; _shelx_res_checksum 9918 _shelx_hkl_file ; -16 0 -2 4.74 5.56 -16 0 -1 -4.53 6.23 -16 0 0 15.60 6.02 -16 0 1 0.06 5.87 -16 0 2 13.22 7.09 -16 0 3 8.31 5.61 -16 2 -3 10.34 6.10 -16 -2 -2 4.95 6.64 -16 2 -2 6.76 5.96 -16 2 -1 20.57 7.27 -16 -2 -1 9.41 6.12 -16 2 0 4.36 5.56 -16 -2 0 5.27 6.24 -16 -2 1 12.23 6.18 -16 2 1 21.96 7.37 -16 2 2 6.03 5.80 -16 -2 2 3.39 5.13 -16 2 3 17.86 6.62 -16 -2 3 22.33 6.53 -16 4 -3 6.22 6.90 -16 4 -2 -11.12 7.47 -16 -4 -1 5.47 6.04 -16 4 -1 -2.46 5.08 -16 -4 0 5.64 5.71 -16 4 0 12.32 6.85 -16 -4 1 -4.70 5.65 -16 4 1 -1.31 5.73 -16 -4 2 27.10 8.11 -16 4 2 16.42 7.07 -16 6 0 7.49 6.13 -16 6 1 21.33 7.27 -15 1 -6 3.40 6.24 -15 -1 -5 31.60 8.21 -15 1 -5 21.24 7.31 -15 -1 -4 19.63 7.53 -15 1 -4 5.53 5.94 -15 -1 -3 13.22 6.53 -15 1 -3 13.99 6.33 -15 -1 -2 6.82 5.11 -15 1 -2 8.84 5.37 -15 -1 -1 14.73 6.17 -15 1 -1 22.75 7.11 -15 1 0 11.23 5.53 -15 -1 0 10.01 5.71 -15 -1 1 5.75 5.89 -15 1 1 12.53 5.35 -15 -1 2 4.30 5.80 -15 1 2 11.57 5.50 -15 -1 3 27.42 7.20 -15 1 3 23.45 6.44 -15 -1 4 6.24 5.56 -15 1 4 20.59 6.27 -15 1 5 18.02 5.84 -15 -1 5 16.80 6.08 -15 1 6 8.63 5.45 -15 -1 6 3.25 4.47 -15 3 -6 5.02 6.98 -15 -3 -5 -0.11 6.09 -15 3 -5 1.26 5.85 -15 -3 -4 -0.11 5.71 -15 3 -4 12.67 6.25 -15 3 -3 9.46 5.42 -15 -3 -3 15.33 6.72 -15 3 -2 2.66 5.34 -15 -3 -2 15.66 6.41 -15 -3 -1 2.73 5.28 -15 3 -1 2.17 4.73 -15 3 0 -1.14 5.35 -15 -3 0 16.51 6.30 -15 -3 1 2.29 5.28 -15 3 1 -0.27 5.52 -15 -3 2 16.28 6.44 -15 3 2 30.91 7.41 -15 3 3 8.97 6.41 -15 -3 3 11.63 6.29 -15 -3 4 18.65 6.27 -15 3 4 16.45 5.85 -15 3 5 8.40 5.64 -15 -3 5 7.06 5.74 -15 -3 6 5.56 5.97 -15 3 6 -0.79 5.09 -15 -5 -4 3.01 5.41 -15 5 -3 2.85 5.67 -15 -5 -3 17.88 6.61 -15 -5 -2 -4.90 5.74 -15 5 -2 3.98 5.65 -15 -5 -1 19.16 6.46 -15 5 -1 12.40 5.95 -15 -5 0 3.03 5.37 -15 5 0 0.45 5.60 -15 5 1 8.05 6.31 -15 -5 1 2.75 4.72 -15 -5 2 -2.67 4.78 -15 5 2 1.56 5.50 -15 -5 3 18.11 6.23 -15 5 3 32.06 7.38 -15 -5 4 1.22 5.36 -15 5 4 -0.18 4.85 -15 5 5 9.48 5.76 -15 -7 -3 6.36 6.03 -15 -7 -2 21.50 7.57 -15 7 -2 24.64 7.71 -15 7 -1 7.23 6.19 -15 7 0 9.65 6.37 -15 7 1 7.10 6.40 -15 7 2 18.69 6.87 -15 7 3 7.35 6.22 -15 7 4 4.47 5.84 -14 0 -7 -2.15 5.92 -14 0 -6 13.45 6.34 -14 0 -5 6.97 6.03 -14 0 -4 35.16 7.47 -14 0 -3 2.23 5.13 -14 0 -2 28.71 7.06 -14 0 -1 1.43 5.21 -14 0 0 71.38 9.10 -14 0 1 1.86 5.31 -14 0 2 66.94 8.56 -14 0 3 8.73 5.57 -14 0 4 8.13 5.86 -14 0 5 4.85 4.83 -14 0 6 55.23 8.12 -14 0 7 -9.39 6.04 -14 0 8 28.31 6.62 -14 2 -8 -2.17 6.22 -14 2 -7 23.17 7.67 -14 -2 -7 15.02 7.02 -14 2 -6 3.79 5.07 -14 -2 -6 5.45 6.12 -14 -2 -5 3.77 5.02 -14 2 -5 10.19 5.49 -14 -2 -4 8.99 5.45 -14 2 -4 8.02 5.54 -14 -2 -3 27.08 7.14 -14 2 -3 33.90 7.14 -14 -2 -2 -2.00 4.79 -14 2 -2 5.02 4.88 -14 2 -1 8.83 5.54 -14 -2 -1 16.58 5.53 -14 2 0 0.96 5.19 -14 -2 0 4.52 4.74 -14 2 1 55.66 7.73 -14 -2 1 64.97 8.28 -14 -2 2 5.25 5.07 -14 2 2 12.96 5.42 -14 2 3 44.80 7.79 -14 -2 3 40.22 6.73 -14 -2 4 4.41 4.89 -14 2 4 -8.34 5.41 -14 -2 5 15.60 5.38 -14 2 5 16.82 6.23 -14 2 6 -1.22 4.47 -14 -2 6 4.07 5.76 -14 -2 7 17.88 5.83 -14 2 7 31.77 6.91 -14 2 8 3.79 5.28 -14 -2 8 -4.04 4.83 -14 -4 -7 8.97 6.45 -14 4 -7 4.96 5.97 -14 4 -6 22.82 7.14 -14 4 -6 7.92 5.75 -14 -4 -6 31.21 7.84 -14 -4 -5 6.70 5.85 -14 4 -5 5.97 5.74 -14 -4 -4 20.93 6.74 -14 4 -4 16.96 5.63 -14 -4 -3 12.87 6.57 -14 4 -3 2.48 5.04 -14 -4 -2 14.38 5.90 -14 4 -2 16.06 5.75 -14 -4 -1 7.46 5.06 -14 4 -1 4.98 4.91 -14 -4 0 31.11 6.65 -14 4 0 46.90 7.80 -14 4 1 -1.89 5.04 -14 -4 1 -9.92 5.97 -14 -4 2 7.22 5.12 -14 4 2 -4.05 4.69 -14 4 3 17.67 5.60 -14 -4 3 17.68 5.84 -14 4 4 25.10 6.51 -14 -4 4 26.41 6.26 -14 -4 5 11.64 5.52 -14 4 5 8.57 5.51 -14 -4 6 17.29 5.45 -14 4 6 11.96 5.88 -14 4 7 2.16 5.54 -14 -4 7 16.98 6.54 -14 6 -6 9.75 6.35 -14 -6 -6 10.42 5.83 -14 6 -5 14.58 7.10 -14 -6 -5 8.59 5.95 -14 -6 -4 2.94 5.15 -14 -6 -3 15.03 6.33 -14 -6 -2 8.41 5.49 -14 -6 -1 4.92 4.74 -14 6 -1 16.91 6.35 -14 6 0 9.36 5.88 -14 -6 0 7.38 4.45 -14 -6 1 27.36 6.47 -14 6 1 24.62 6.90 -14 6 2 4.66 5.71 -14 6 3 35.91 7.87 -14 6 4 11.45 6.44 -14 6 4 12.62 6.09 -14 6 5 7.66 5.24 -14 6 5 32.42 7.63 -14 6 6 16.45 6.96 -14 6 6 24.55 6.84 -14 6 7 17.98 6.45 -14 6 7 17.69 7.42 -14 -8 -5 3.53 5.91 -14 8 -4 0.19 6.33 -14 8 -3 11.17 6.19 -14 8 -2 7.74 5.29 -14 8 -1 10.01 6.67 -14 8 0 4.87 5.55 -14 8 1 19.17 6.46 -14 8 2 11.65 6.19 -14 8 3 10.98 5.70 -14 8 4 17.37 6.62 -14 8 5 -6.26 6.51 -14 8 6 8.85 6.17 -14 10 -2 12.41 6.27 -13 -1 -9 -1.56 5.60 -13 1 -9 9.24 6.11 -13 -1 -8 7.49 5.69 -13 1 -8 4.76 5.70 -13 1 -7 13.11 6.93 -13 -1 -7 11.71 6.29 -13 1 -6 6.12 5.47 -13 -1 -6 16.44 6.76 -13 1 -5 40.22 7.68 -13 -1 -5 43.05 7.60 -13 -1 -4 4.21 5.04 -13 1 -4 10.89 5.25 -13 -1 -3 54.23 8.29 -13 1 -3 51.10 7.63 -13 -1 -2 32.65 6.79 -13 1 -2 31.22 7.12 -13 -1 -1 57.09 8.17 -13 1 -1 51.29 7.36 -13 -1 0 14.77 5.62 -13 1 0 13.55 5.16 -13 -1 1 43.39 6.96 -13 1 1 49.69 7.26 -13 1 2 49.91 7.05 -13 -1 2 55.26 7.17 -13 1 3 13.72 5.72 -13 -1 3 8.97 4.84 -13 -1 4 39.76 7.00 -13 1 4 54.40 7.62 -13 1 5 35.16 6.67 -13 -1 5 34.53 6.84 -13 1 6 6.12 4.99 -13 -1 6 5.69 4.22 -13 1 7 37.93 7.26 -13 -1 7 33.17 6.96 -13 1 8 35.60 7.27 -13 -1 8 24.67 6.30 -13 -1 9 15.66 5.55 -13 1 9 36.07 6.88 -13 1 10 9.43 6.43 -13 3 -9 0.76 6.01 -13 -3 -8 9.64 6.05 -13 3 -8 3.01 6.10 -13 3 -7 -3.72 5.30 -13 -3 -7 13.81 5.94 -13 -3 -6 5.62 5.75 -13 3 -6 10.54 5.69 -13 3 -5 9.58 6.03 -13 -3 -5 8.31 6.23 -13 3 -4 12.28 5.77 -13 -3 -4 11.48 5.70 -13 -3 -3 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-5 -13 38.15 7.22 5 -5 -12 11.04 4.99 5 -5 -11 93.20 9.11 5 5 -2 39.02 4.62 5 5 -1 652.02 13.38 5 -5 0 128.51 7.85 5 5 0 128.52 5.98 5 -5 1 901.60 18.29 5 -7 -13 1.14 4.52 5 -7 -12 51.51 8.38 5 -7 -11 4.49 4.84 5 -7 -10 60.56 7.74 5 7 -3 96.11 6.84 5 7 -2 813.56 17.14 5 7 -1 57.12 5.16 5 7 0 764.70 15.55 5 7 1 1.89 2.37 5 7 2 588.65 13.45 5 7 3 0.98 2.22 5 7 4 435.01 11.86 5 -9 -13 11.63 6.33 5 -9 -12 -0.51 4.38 5 -9 -11 44.98 8.01 5 -9 -10 6.27 4.89 5 -9 -9 50.10 7.12 5 9 -6 10.04 4.71 5 9 -5 111.18 8.25 5 9 -4 10.42 4.31 5 9 -3 96.08 7.29 5 9 -2 12.43 3.98 5 9 -1 191.78 9.19 5 9 0 3.10 2.71 5 9 1 110.49 7.04 5 9 2 1.49 2.60 5 9 3 51.09 5.11 5 9 4 -0.15 2.56 5 9 5 120.01 7.45 5 11 -11 17.11 6.05 5 11 -10 21.51 5.89 5 11 -9 20.39 5.94 5 11 -8 21.75 5.36 5 11 -7 15.66 4.97 5 11 -6 17.49 5.06 5 11 -5 -2.91 4.17 5 11 -4 76.74 7.25 5 11 -3 28.48 4.91 5 11 -2 21.53 4.38 5 11 -1 25.42 5.13 5 11 0 84.27 7.03 5 11 1 20.68 4.11 5 11 2 75.12 6.53 5 11 3 38.13 5.20 5 11 4 51.13 5.76 5 11 5 2.94 3.31 5 13 -10 3.50 4.16 5 13 -9 24.11 5.88 5 13 -8 4.39 3.84 5 13 -7 13.94 4.71 5 13 -6 -4.75 4.61 5 13 -5 78.48 8.14 5 13 -4 24.60 5.20 5 13 -3 36.57 6.29 5 13 -2 5.56 4.30 5 13 -1 57.96 6.85 5 13 0 7.42 3.75 5 13 1 42.82 6.13 5 13 2 -0.08 3.46 5 13 3 42.06 5.92 5 13 4 0.24 3.49 5 13 5 25.78 5.32 5 15 -8 0.48 5.09 5 15 -7 -10.69 5.93 5 15 -6 -10.83 5.36 5 15 -5 1.31 3.76 5 15 -4 9.73 5.25 5 15 -3 11.69 4.85 5 15 -2 15.40 5.26 5 15 -1 3.98 3.69 5 15 0 7.09 4.11 5 15 1 -3.92 3.88 5 15 2 8.80 4.48 5 15 3 3.97 4.28 5 15 4 15.35 5.10 5 15 5 7.93 4.42 5 17 -4 1.89 3.86 5 17 -3 -0.38 4.28 5 17 -2 9.26 4.93 5 17 -1 6.65 4.10 5 17 0 7.44 5.57 5 17 1 0.71 3.96 5 17 2 3.20 3.99 5 17 3 0.92 4.25 5 17 4 9.56 5.18 5 17 5 7.63 5.11 6 0 -14 43.67 7.91 6 0 -13 -3.45 4.37 6 0 -12 108.51 9.75 6 -2 -14 -1.67 5.01 6 2 -13 19.24 5.73 6 -2 -13 26.48 6.97 6 -2 -12 -3.30 4.27 6 2 -12 2.11 3.74 6 -4 -14 10.13 5.51 6 -4 -13 3.58 5.48 6 -4 -12 40.86 7.24 6 4 -1 155.72 6.88 6 -6 -13 28.29 7.19 6 -6 -12 10.25 5.25 6 -6 -11 51.66 7.56 6 6 -2 110.72 6.90 6 6 -1 603.10 14.05 6 6 0 220.68 8.37 6 6 1 365.58 10.24 6 6 2 197.21 7.55 6 -8 -13 8.76 5.68 6 -8 -12 14.73 6.30 6 -8 -11 3.51 4.68 6 -8 -10 39.31 6.96 6 8 -5 176.49 9.97 6 8 -4 157.22 9.20 6 8 -3 144.91 8.57 6 8 -2 133.40 7.85 6 8 -1 88.85 6.43 6 8 0 133.63 7.41 6 8 1 64.15 5.34 6 8 2 147.89 7.45 6 8 3 52.77 4.84 6 -10 -12 6.80 5.85 6 -10 -11 1.87 5.10 6 10 -8 17.66 5.69 6 10 -7 34.39 6.11 6 10 -6 67.77 7.24 6 10 -5 6.62 4.52 6 10 -4 32.21 5.50 6 10 -3 2.06 3.74 6 10 -2 9.99 3.82 6 10 -1 55.41 5.96 6 10 0 75.12 6.47 6 10 1 38.22 4.82 6 10 2 39.27 5.06 6 10 3 39.31 4.80 6 10 4 75.96 6.47 6 12 -10 10.48 5.71 6 12 -9 30.24 6.59 6 12 -8 9.14 5.10 6 12 -7 38.96 6.73 6 12 -6 6.26 4.59 6 12 -5 21.54 5.19 6 12 -4 15.19 4.96 6 12 -3 59.10 6.62 6 12 -2 7.30 3.91 6 12 -1 36.68 5.76 6 12 0 -1.46 3.08 6 12 1 47.25 5.94 6 12 2 9.88 3.75 6 12 3 45.80 5.93 6 12 4 1.98 3.35 6 14 -8 3.04 4.79 6 14 -7 3.13 4.52 6 14 -6 7.94 4.51 6 14 -5 -3.05 4.69 6 14 -4 18.95 5.63 6 14 -3 4.93 4.41 6 14 -2 36.14 6.22 6 14 -1 6.97 4.34 6 14 0 20.52 5.41 6 14 1 -1.86 3.84 6 14 2 11.80 4.52 6 14 3 4.29 4.23 6 14 4 9.48 4.15 6 14 5 5.81 3.74 6 16 -5 1.46 3.90 6 16 -4 5.88 4.74 6 16 -3 8.32 5.21 6 16 -2 -0.96 3.97 6 16 -1 9.33 5.02 6 16 0 0.03 3.88 6 16 1 1.38 4.52 6 16 2 5.82 4.90 6 16 3 10.28 5.02 6 16 4 6.77 4.25 6 16 5 -0.14 3.99 7 -1 -14 17.46 6.55 7 1 -14 9.59 5.44 7 -1 -13 46.48 7.46 7 1 -13 42.35 7.12 7 -3 -14 11.68 6.10 7 -3 -13 1.58 4.85 7 -5 -13 37.03 7.56 7 -5 -12 -1.08 4.84 7 5 -2 20.42 4.32 7 5 -1 287.39 9.82 7 5 0 9.93 2.67 7 -7 -12 44.27 8.07 7 7 -3 50.14 6.09 7 7 -2 358.48 12.30 7 7 -1 29.03 4.33 7 7 0 261.58 9.81 7 7 1 3.90 2.66 7 -9 -12 0.33 5.29 7 -9 -11 17.18 6.44 7 9 -6 23.19 6.15 7 9 -5 41.73 6.14 7 9 -4 2.78 4.11 7 9 -3 105.32 8.12 7 9 -2 3.52 4.04 7 9 -1 79.24 6.44 7 9 0 5.51 3.47 7 9 1 56.88 5.42 7 11 -10 19.87 6.08 7 11 -9 10.28 5.72 7 11 -8 26.80 6.46 7 11 -7 14.83 5.44 7 11 -6 5.90 3.75 7 11 -5 1.97 3.97 7 11 -4 21.46 4.74 7 11 -3 -4.82 4.45 7 11 -2 43.65 5.87 7 11 -1 14.93 4.37 7 11 0 44.49 5.57 7 11 1 36.15 5.51 7 11 2 55.15 6.08 7 13 -9 22.23 6.24 7 13 -8 0.67 4.89 7 13 -7 24.35 6.07 7 13 -6 3.67 4.60 7 13 -5 24.54 5.88 7 13 -4 5.81 4.00 7 13 -3 52.55 7.19 7 13 -2 13.66 4.65 7 13 -1 29.18 5.65 7 13 0 5.52 4.25 7 13 1 16.68 4.29 7 13 2 2.14 3.52 7 13 3 13.99 4.45 7 15 -6 6.17 5.34 7 15 -5 1.10 4.46 7 15 -4 8.41 5.14 7 15 -3 6.02 4.81 7 15 -2 13.48 5.00 7 15 -1 4.51 4.61 7 15 0 -3.25 4.44 7 15 1 2.02 4.28 7 15 2 3.92 4.79 7 15 3 -1.65 3.72 7 17 -2 4.84 5.38 7 17 -1 3.15 5.09 7 17 0 0.71 4.23 7 17 1 6.36 5.35 7 17 2 -2.39 4.66 7 17 3 -3.28 4.65 7 17 4 -0.55 1.67 8 0 -14 69.88 9.28 8 -4 -13 18.45 6.90 8 6 -3 154.81 8.79 8 6 -2 35.91 5.19 8 6 -1 262.60 10.11 8 -8 -12 15.42 6.03 8 8 -5 29.67 5.79 8 8 -4 157.91 9.48 8 8 -3 91.41 7.54 8 8 -2 76.56 6.68 8 8 -1 45.04 5.41 8 10 -8 63.65 8.25 8 10 -7 18.61 5.85 8 10 -6 22.68 5.85 8 10 -5 9.40 4.82 8 10 -4 33.39 5.61 8 10 -3 9.16 4.35 8 10 -2 9.00 4.34 8 10 -1 5.35 3.88 8 10 0 69.80 6.55 8 12 -9 26.55 6.96 8 12 -8 14.69 6.07 8 12 -7 23.52 6.03 8 12 -6 6.71 4.80 8 12 -5 31.39 5.77 8 12 -4 4.49 3.86 8 12 -3 7.69 4.73 8 12 -2 17.12 5.05 8 12 -1 40.29 6.05 8 12 0 3.03 3.82 8 12 1 14.37 4.29 8 14 -7 2.23 5.12 8 14 -6 2.03 4.94 8 14 -5 0.67 4.37 8 14 -4 11.58 4.42 8 14 -3 4.15 4.32 8 14 -2 13.45 5.33 8 14 -1 2.31 4.40 8 14 0 14.80 4.81 8 14 1 -2.04 3.91 8 16 -3 8.41 5.19 8 16 -2 -2.36 4.37 8 16 -1 4.65 5.30 8 16 0 -5.67 4.73 8 16 1 5.56 4.39 8 16 2 -0.98 4.50 9 7 -4 145.14 9.44 9 7 -3 16.00 4.72 9 9 -7 107.21 9.35 9 9 -6 7.52 5.11 9 9 -5 48.69 6.75 9 9 -4 8.16 4.91 9 9 -3 66.13 6.80 9 9 -2 11.74 4.17 9 11 -9 22.99 7.40 9 11 -8 20.20 6.37 9 11 -7 19.58 5.86 9 11 -6 14.95 5.72 9 11 -5 1.22 4.25 9 11 -4 11.13 4.70 9 11 -3 3.87 4.44 9 11 -2 12.97 4.64 9 11 -1 2.20 3.23 9 13 -7 11.69 5.84 9 13 -6 -2.13 5.01 9 13 -5 6.10 5.27 9 13 -4 5.54 4.30 9 13 -3 15.24 5.53 9 13 -2 -0.39 3.89 9 13 -1 28.04 5.78 9 15 -4 12.13 5.58 9 15 -3 1.97 4.68 9 15 -2 4.72 4.87 9 15 -1 2.47 4.28 9 15 0 7.82 4.76 10 8 -5 61.63 7.59 10 8 -4 59.30 7.06 10 10 -9 20.71 6.81 10 10 -8 27.81 6.96 10 10 -7 30.91 6.88 10 10 -6 22.64 5.63 10 10 -5 3.74 4.80 10 10 -4 10.43 5.07 10 12 -7 10.05 4.67 10 12 -6 7.48 4.47 10 12 -5 20.14 5.95 10 12 -4 2.43 4.74 10 12 -3 8.83 4.09 10 14 -5 -5.14 6.07 10 14 -4 -3.84 5.28 10 14 -3 0.61 4.16 11 9 -8 31.62 7.33 11 9 -7 29.99 7.01 11 9 -6 10.61 5.48 11 11 -8 8.00 5.56 11 11 -7 6.80 5.63 11 11 -6 6.04 5.05 11 11 -5 -2.06 4.87 11 13 -5 0.21 5.50 12 10 -7 5.19 5.68 TITL B125_1 in Cc REM Cc (#9 in standard setting) CELL 0.71073 13.086765 15.037768 12.444226 90.0000 91.3168 90.0000 ZERR 11.00 0.001107 0.001430 0.000945 0.0000 0.0075 0.0000 LATT -7 SYMM x,-y, z+1/2 SFAC C H N O UNIT 121.00 110.00 11.00 11.00 TREF HKLF 4 END _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' ; _shelx_hkl_checksum 22830 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 Ag1 Ag 0.5000 0.36023(3) 0.7500 0.06432(18) Uani 1 2 d S T P . . Cl1 Cl 0.5000 0.51361(12) 0.7500 0.1102(7) Uani 1 2 d S T P . . N1 N 0.5255(2) 0.1677(2) 0.6688(2) 0.0603(8) Uani 1 1 d . . . . . C1 C 0.5000 0.2228(4) 0.7500 0.0580(14) Uani 1 2 d S T P . . C2 C 0.5157(3) 0.0797(3) 0.6987(3) 0.0724(11) Uani 1 1 d . . . . . H2 H 0.5282 0.0301 0.6563 0.087 Uiso 1 1 calc R U . . . C3 C 0.5523(3) 0.2005(3) 0.5609(3) 0.0613(10) Uani 1 1 d . . . . . H3 H 0.5784 0.2611 0.5704 0.074 Uiso 1 1 calc R U . . . C6 C 0.8041(4) 0.0785(4) 0.5476(6) 0.1174(19) Uani 1 1 d . . . . . H6 H 0.8588 0.0659 0.5940 0.141 Uiso 1 1 calc R U . . . C5 C 0.7228(3) 0.1259(3) 0.5832(4) 0.0907(14) Uani 1 1 d . . . . . H5 H 0.7235 0.1459 0.6540 0.109 Uiso 1 1 calc R U . . . C4 C 0.6395(3) 0.1450(3) 0.5173(3) 0.0678(10) Uani 1 1 d . . . . . C9 C 0.6408(3) 0.1162(3) 0.4125(3) 0.0888(14) Uani 1 1 d . . . . . H9 H 0.5859 0.1285 0.3661 0.107 Uiso 1 1 calc R U . . . C8 C 0.7251(5) 0.0682(4) 0.3757(5) 0.120(2) Uani 1 1 d . . . . . H8 H 0.7263 0.0491 0.3047 0.144 Uiso 1 1 calc R U . . . C7 C 0.8051(5) 0.0497(4) 0.4440(7) 0.125(2) Uani 1 1 d . . . . . H7 H 0.8605 0.0173 0.4197 0.150 Uiso 1 1 calc R U . . . C10 C 0.4586(3) 0.2067(3) 0.4876(3) 0.0655(11) Uani 1 1 d . . . . . C11 C 0.3833(3) 0.1432(3) 0.4834(3) 0.0865(14) Uani 1 1 d . . . . . H11 H 0.3881 0.0939 0.5283 0.104 Uiso 1 1 calc R U . . . C12 C 0.3008(4) 0.1516(4) 0.4137(4) 0.1053(17) Uani 1 1 d . . . . . H12 H 0.2505 0.1079 0.4115 0.126 Uiso 1 1 calc R U . . . C13 C 0.2925(4) 0.2233(4) 0.3482(4) 0.1047(17) Uani 1 1 d . . . . . H13 H 0.2365 0.2287 0.3012 0.126 Uiso 1 1 calc R U . . . C14 C 0.3659(4) 0.2876(4) 0.3511(4) 0.1093(18) Uani 1 1 d . . . . . H14 H 0.3604 0.3367 0.3059 0.131 Uiso 1 1 calc R U . . . C15 C 0.4486(3) 0.2795(3) 0.4216(3) 0.0903(15) Uani 1 1 d . . . . . H15 H 0.4981 0.3238 0.4243 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 Ag1 0.0595(3) 0.0822(3) 0.0516(3) 0.000 0.00784(18) 0.000 Cl1 0.1503(17) 0.0850(11) 0.0979(13) 0.000 0.0569(12) 0.000 N1 0.069(2) 0.078(2) 0.0341(15) -0.0005(15) 0.0024(14) -0.0044(16) C1 0.053(3) 0.084(4) 0.037(3) 0.000 -0.002(2) 0.000 C2 0.095(3) 0.079(3) 0.043(2) -0.002(2) 0.003(2) -0.001(2) C3 0.062(2) 0.083(3) 0.0392(19) 0.0003(19) 0.0036(17) -0.017(2) C6 0.064(3) 0.127(5) 0.161(6) -0.010(5) 0.018(4) -0.022(3) C5 0.062(3) 0.116(4) 0.094(3) -0.019(3) -0.001(3) -0.012(3) C4 0.056(2) 0.090(3) 0.058(2) -0.011(2) 0.0123(18) -0.022(2) C9 0.079(3) 0.128(4) 0.061(3) -0.019(3) 0.023(2) -0.026(3) C8 0.119(5) 0.144(5) 0.100(4) -0.030(4) 0.063(4) -0.028(4) C7 0.080(4) 0.113(5) 0.185(8) -0.001(5) 0.068(5) -0.016(4) C10 0.059(2) 0.104(3) 0.0337(19) 0.006(2) 0.0070(17) -0.017(2) C11 0.078(3) 0.124(4) 0.056(2) 0.026(3) -0.009(2) -0.034(3) C12 0.085(3) 0.154(5) 0.077(3) 0.037(3) -0.014(3) -0.057(3) C13 0.073(3) 0.162(5) 0.077(3) 0.038(3) -0.022(2) -0.034(3) C14 0.090(4) 0.146(5) 0.091(4) 0.051(3) -0.024(3) -0.039(4) C15 0.072(3) 0.127(4) 0.071(3) 0.027(3) -0.014(2) -0.039(3) 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 C1 Ag1 Cl1 180.0 . . ? C1 N1 C2 111.1(3) . . ? C1 N1 C3 122.7(3) . . ? C2 N1 C3 126.1(3) . . ? N1 C1 Ag1 127.8(2) . . ? N1 C1 Ag1 127.8(2) 2_656 . ? N1 C1 N1 104.5(4) 2_656 . ? N1 C2 H2 126.7 . . ? C2 C2 N1 106.65(18) 2_656 . ? C2 C2 H2 126.7 2_656 . ? N1 C3 H3 106.9 . . ? N1 C3 C4 109.6(3) . . ? N1 C3 C10 111.2(3) . . ? C4 C3 H3 106.9 . . ? C10 C3 H3 106.9 . . ? C10 C3 C4 114.9(3) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C7 C6 C5 120.0(6) . . ? C6 C5 H5 119.1 . . ? C6 C5 C4 121.8(5) . . ? C4 C5 H5 119.1 . . ? C5 C4 C3 119.3(3) . . ? C9 C4 C3 122.5(4) . . ? C9 C4 C5 118.1(4) . . ? C4 C9 H9 120.0 . . ? C4 C9 C8 119.9(5) . . ? C8 C9 H9 120.0 . . ? C9 C8 H8 120.0 . . ? C7 C8 C9 120.0(5) . . ? C7 C8 H8 120.0 . . ? C6 C7 C8 120.1(6) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C11 C10 C3 123.4(4) . . ? C11 C10 C15 118.3(4) . . ? C15 C10 C3 118.3(4) . . ? C10 C11 H11 119.6 . . ? C10 C11 C12 120.9(4) . . ? C12 C11 H11 119.6 . . ? C11 C12 H12 119.9 . . ? C13 C12 C11 120.2(4) . . ? C13 C12 H12 119.9 . . ? C12 C13 H13 119.9 . . ? C12 C13 C14 120.2(5) . . ? C14 C13 H13 119.9 . . ? C13 C14 H14 120.2 . . ? C13 C14 C15 119.7(5) . . ? C15 C14 H14 120.2 . . ? C10 C15 C14 120.8(4) . . ? C10 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? 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 Ag1 Cl1 2.3065(18) . ? Ag1 C1 2.066(5) . ? N1 C1 1.355(4) . ? N1 C2 1.381(5) . ? N1 C3 1.480(4) . ? C1 N1 1.355(4) 2_656 ? C2 C2 1.351(7) 2_656 ? C2 H2 0.9300 . ? C3 H3 0.9800 . ? C3 C4 1.524(5) . ? C3 C10 1.515(5) . ? C6 H6 0.9300 . ? C6 C5 1.363(7) . ? C6 C7 1.360(8) . ? C5 H5 0.9300 . ? C5 C4 1.380(6) . ? C4 C9 1.374(5) . ? C9 H9 0.9300 . ? C9 C8 1.404(7) . ? C8 H8 0.9300 . ? C8 C7 1.362(8) . ? C7 H7 0.9300 . ? C10 C11 1.372(5) . ? C10 C15 1.373(5) . ? C11 H11 0.9300 . ? C11 C12 1.375(6) . ? C12 H12 0.9300 . ? C12 C13 1.354(6) . ? C13 H13 0.9300 . ? C13 C14 1.363(6) . ? C14 H14 0.9300 . ? C14 C15 1.383(6) . ? C15 H15 0.9300 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C3 C4 C5 -45.7(5) . . . . ? N1 C3 C4 C9 137.2(4) . . . . ? N1 C3 C10 C11 -41.6(5) . . . . ? N1 C3 C10 C15 138.6(4) . . . . ? C1 N1 C2 C2 -0.6(5) . . . 2_656 ? C1 N1 C3 C4 141.3(3) . . . . ? C1 N1 C3 C10 -90.5(4) . . . . ? C2 N1 C1 Ag1 -179.8(2) . . . . ? C2 N1 C1 N1 0.2(2) . . . 2_656 ? C2 N1 C3 C4 -43.6(5) . . . . ? C2 N1 C3 C10 84.6(4) . . . . ? C3 N1 C1 Ag1 -4.0(3) . . . . ? C3 N1 C1 N1 176.0(3) . . . 2_656 ? C3 N1 C2 C2 -176.2(4) . . . 2_656 ? C3 C4 C9 C8 177.6(4) . . . . ? C3 C10 C11 C12 -178.8(4) . . . . ? C3 C10 C15 C14 178.5(4) . . . . ? C6 C5 C4 C3 -178.3(4) . . . . ? C6 C5 C4 C9 -1.1(7) . . . . ? C5 C6 C7 C8 0.1(9) . . . . ? C5 C4 C9 C8 0.5(6) . . . . ? C4 C3 C10 C11 83.7(4) . . . . ? C4 C3 C10 C15 -96.1(5) . . . . ? C4 C9 C8 C7 0.5(8) . . . . ? C9 C8 C7 C6 -0.8(9) . . . . ? C7 C6 C5 C4 0.8(8) . . . . ? C10 C3 C4 C5 -171.8(4) . . . . ? C10 C3 C4 C9 11.1(5) . . . . ? C10 C11 C12 C13 -0.3(8) . . . . ? C11 C10 C15 C14 -1.3(7) . . . . ? C11 C12 C13 C14 0.0(8) . . . . ? C12 C13 C14 C15 -0.3(9) . . . . ? C13 C14 C15 C10 1.0(8) . . . . ? C15 C10 C11 C12 1.0(7) . . . . ?