#------------------------------------------------------------------------------ #$Date: 2020-06-03 04:58:42 +0300 (Wed, 03 Jun 2020) $ #$Revision: 252560 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/45/7704572.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_7704572 loop_ _publ_author_name 'Kordestani, Nazanin' 'Amiri Rudbari, Hadi' 'Bruno, Giuseppe' 'Scopelliti, Rosario' 'Braun, Jason D.' 'Herbert, David E.' 'Blacque, Olivier' 'Correia, Isabel' 'Zaman, Mohammad Al-moktadir' 'Bindu, Mortuza Mamun' 'Janiak, Christoph' 'Enamullah, Mohammed' _publ_section_title ; Solid-state to solution helicity inversion of pseudotetrahedral chiral copper(II) complexes with 2,4-dihalo-salicylaldiminate ligands ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D0DT01649G _journal_year 2020 _chemical_absolute_configuration rmad _chemical_formula_sum 'C30 H24 Cu I4 N2 O2' _chemical_formula_weight 1015.65 _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2019-07-26 deposited with the CCDC. 2020-06-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 118.2090(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 14.5586(3) _cell_length_b 11.1467(2) _cell_length_c 10.6165(2) _cell_measurement_reflns_used 9868 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 40.13 _cell_measurement_theta_min 2.42 _cell_volume 1518.23(5) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_unetI/netI 0.0256 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 39452 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 42.233 _diffrn_reflns_theta_min 2.420 _exptl_absorpt_coefficient_mu 4.817 _exptl_absorpt_correction_T_max 0.617 _exptl_absorpt_correction_T_min 0.449 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS; Bruker, 2008' _exptl_crystal_colour green _exptl_crystal_density_diffrn 2.222 _exptl_crystal_description irregular _exptl_crystal_F_000 950 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _refine_diff_density_max 1.915 _refine_diff_density_min -0.827 _refine_diff_density_rms 0.209 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.022(18) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 178 _refine_ls_number_reflns 10671 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0329 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+0.3211P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0801 _refine_ls_wR_factor_ref 0.0844 _reflns_Friedel_coverage 0.931 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.997 _reflns_number_gt 9091 _reflns_number_total 10671 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt01649g2.cif _cod_data_source_block shelx_CCDC4 _cod_original_cell_volume 1518.22(5) _cod_original_sg_symbol_H-M 'C 2' _cod_database_code 7704572 _shelx_shelxl_version_number 2016/6 _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_res_file ; TITL SIR97 run in space group C 2 shelx.res created by SHELXL-2016/6 at 09:49:12 on 17-May-2019 CELL 0.71073 14.5586 11.1467 10.6165 90.000 118.209 90.000 ZERR 2.00 0.0003 0.0002 0.0002 0.000 0.001 0.000 LATT -7 SYMM - X, Y, - Z SFAC C H N O CU I UNIT 60 48 4 4 2 8 MERG 2 FMAP 2 PLAN 25 TWIN ACTA BOND $H CONF L.S. 10 TEMP 0.00 WGHT 0.045900 0.321100 BASF 0.02172 FVAR 0.08477 I1 6 0.820880 1.006848 0.889138 11.00000 0.02471 0.04124 = 0.03160 -0.01348 0.00795 -0.00082 I2 6 1.051250 0.654383 0.717339 11.00000 0.02909 0.06997 = 0.04351 0.00540 0.01526 0.02428 CU1 5 0.500000 0.834534 0.500000 10.50000 0.01486 0.03710 = 0.01773 0.00000 0.00573 0.00000 C1 1 0.634513 0.728483 0.399519 11.00000 0.02173 0.03749 = 0.02242 -0.00626 0.00808 0.00313 AFIX 43 H1 2 0.645900 0.678551 0.338082 11.00000 -1.20000 AFIX 0 N1 3 0.539172 0.757796 0.359809 11.00000 0.02059 0.03590 = 0.01957 -0.00671 0.00656 -0.00072 O1 4 0.636809 0.887944 0.621113 11.00000 0.01442 0.03858 = 0.02627 -0.00922 0.00655 0.00164 C2 1 0.725611 0.764436 0.528628 11.00000 0.01824 0.03595 = 0.02155 -0.00449 0.00748 0.00193 C7 1 0.722375 0.847093 0.628033 11.00000 0.01487 0.02918 = 0.02108 -0.00192 0.00611 0.00230 C4 1 0.913109 0.745058 0.668663 11.00000 0.01936 0.04410 = 0.02889 -0.00013 0.00960 0.00888 C3 1 0.820886 0.712838 0.552109 11.00000 0.02263 0.04380 = 0.02743 -0.00336 0.01133 0.00743 AFIX 43 H3 2 0.821353 0.656320 0.487974 11.00000 -1.20000 AFIX 0 C6 1 0.820107 0.883950 0.739924 11.00000 0.01622 0.03309 = 0.02290 -0.00455 0.00566 0.00125 C10 1 0.378479 0.640345 0.224332 11.00000 0.02866 0.03507 = 0.02320 -0.00807 0.00605 -0.00350 C5 1 0.913592 0.834046 0.762095 11.00000 0.01516 0.04284 = 0.02692 -0.00235 0.00521 0.00512 AFIX 43 H5 2 0.976071 0.859323 0.838214 11.00000 -1.20000 AFIX 0 C15 1 0.409764 0.541928 0.317731 11.00000 0.05426 0.03944 = 0.04333 0.00206 0.00811 -0.00454 AFIX 43 H15 2 0.480267 0.524522 0.372428 11.00000 -1.20000 AFIX 0 C8 1 0.461681 0.715557 0.214576 11.00000 0.02482 0.04254 = 0.01961 -0.00812 0.00712 -0.00163 AFIX 13 H8 2 0.498764 0.663087 0.179641 11.00000 -1.20000 AFIX 0 C11 1 0.272717 0.659206 0.139413 11.00000 0.02917 0.04377 = 0.03298 -0.01090 0.00842 -0.00512 AFIX 43 H11 2 0.250354 0.722906 0.075215 11.00000 -1.20000 AFIX 0 C13 1 0.232083 0.490670 0.243513 11.00000 0.06628 0.05875 = 0.06724 -0.01355 0.02980 -0.03317 AFIX 43 H13 2 0.183100 0.440791 0.249539 11.00000 -1.20000 AFIX 0 C12 1 0.199380 0.585065 0.148074 11.00000 0.03846 0.06073 = 0.05116 -0.01947 0.01655 -0.01830 AFIX 43 H12 2 0.128618 0.598885 0.089927 11.00000 -1.20000 AFIX 0 C14 1 0.335509 0.470094 0.328846 11.00000 0.07712 0.04817 = 0.06422 0.00621 0.02553 -0.01814 AFIX 43 H14 2 0.356792 0.407799 0.394932 11.00000 -1.20000 AFIX 0 C9 1 0.422510 0.822516 0.114641 11.00000 0.03989 0.04937 = 0.02723 0.00330 0.01319 -0.00272 AFIX 33 H9A 2 0.372589 0.796029 0.020930 11.00000 -1.50000 H9B 2 0.390113 0.878807 0.149773 11.00000 -1.50000 H9C 2 0.480035 0.860412 0.109964 11.00000 -1.50000 AFIX 0 HKLF 4 REM SIR97 run in space group C 2 REM R1 = 0.0329 for 9091 Fo > 4sig(Fo) and 0.0418 for all 10671 data REM 178 parameters refined using 1 restraints END WGHT 0.0458 0.3310 REM Highest difference peak 1.915, deepest hole -0.827, 1-sigma level 0.209 Q1 1 1.0491 0.7061 0.6928 11.00000 0.05 1.91 Q2 1 1.0363 0.6542 0.7606 11.00000 0.05 1.82 Q3 1 0.8089 0.9936 0.8321 11.00000 0.05 1.78 Q4 1 0.8141 1.0032 0.9374 11.00000 0.05 1.49 Q5 1 1.0313 0.6186 0.6743 11.00000 0.05 1.45 Q6 1 1.0109 0.6831 0.7054 11.00000 0.05 1.03 Q7 1 0.4998 0.8596 0.5498 11.00000 0.05 0.92 Q8 1 0.5183 0.7866 0.5415 11.00000 0.05 0.66 Q9 1 0.1507 0.4719 0.2534 11.00000 0.05 0.61 Q10 1 0.1077 0.5080 0.1247 11.00000 0.05 0.54 Q11 1 0.3778 0.4985 0.3076 11.00000 0.05 0.53 Q12 1 0.3811 0.4497 0.3401 11.00000 0.05 0.53 Q13 1 0.5007 0.9993 0.1230 11.00000 0.05 0.53 Q14 1 0.0470 0.5082 0.0093 11.00000 0.05 0.51 Q15 1 0.1975 0.5081 0.1422 11.00000 0.05 0.50 Q16 1 0.1091 0.4696 0.1867 11.00000 0.05 0.48 Q17 1 0.0513 0.5048 0.0812 11.00000 0.05 0.48 Q18 1 0.8484 0.8292 0.7205 11.00000 0.05 0.47 Q19 1 0.7625 0.6900 0.6670 11.00000 0.05 0.47 Q20 1 0.5000 0.9872 0.0000 10.50000 0.05 0.47 Q21 1 0.1301 0.4582 0.1550 11.00000 0.05 0.46 Q22 1 0.4918 0.9875 0.0516 11.00000 0.05 0.46 Q23 1 0.2211 0.4402 0.2430 11.00000 0.05 0.46 Q24 1 0.3834 0.5837 0.2835 11.00000 0.05 0.46 Q25 1 0.2431 0.6196 0.1283 11.00000 0.05 0.46 ; _shelx_res_checksum 45589 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -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 I1 I 0.82088(2) 1.00685(2) 0.88914(2) 0.03469(5) Uani 1 1 d . . . . . I2 I 1.05125(2) 0.65438(3) 0.71734(3) 0.04829(8) Uani 1 1 d . . . . . Cu1 Cu 0.500000 0.83453(5) 0.500000 0.02403(8) Uani 1 2 d S T P . . C1 C 0.6345(2) 0.7285(3) 0.3995(3) 0.0282(5) Uani 1 1 d . . . . . H1 H 0.645900 0.678551 0.338082 0.034 Uiso 1 1 calc R U . . . N1 N 0.53917(19) 0.7578(2) 0.3598(3) 0.0265(4) Uani 1 1 d . . . . . O1 O 0.63681(15) 0.8879(2) 0.6211(2) 0.0277(4) Uani 1 1 d . . . . . C2 C 0.7256(2) 0.7644(3) 0.5286(3) 0.0260(4) Uani 1 1 d . . . . . C7 C 0.72237(17) 0.8471(2) 0.6280(3) 0.0227(4) Uani 1 1 d . . . . . C4 C 0.9131(2) 0.7451(3) 0.6687(3) 0.0315(5) Uani 1 1 d . . . . . C3 C 0.8209(2) 0.7128(3) 0.5521(3) 0.0315(5) Uani 1 1 d . . . . . H3 H 0.821353 0.656320 0.487974 0.038 Uiso 1 1 calc R U . . . C6 C 0.82011(19) 0.8840(3) 0.7399(3) 0.0255(4) Uani 1 1 d . . . . . C10 C 0.3785(2) 0.6403(3) 0.2243(3) 0.0315(5) Uani 1 1 d . . . . . C5 C 0.91359(19) 0.8340(3) 0.7621(3) 0.0302(5) Uani 1 1 d . . . . . H5 H 0.976071 0.859323 0.838214 0.036 Uiso 1 1 calc R U . . . C15 C 0.4098(5) 0.5419(4) 0.3177(6) 0.0517(11) Uani 1 1 d . . . . . H15 H 0.480267 0.524522 0.372428 0.062 Uiso 1 1 calc R U . . . C8 C 0.4617(2) 0.7156(3) 0.2146(3) 0.0304(5) Uani 1 1 d . . . . . H8 H 0.498764 0.663087 0.179641 0.036 Uiso 1 1 calc R U . . . C11 C 0.2727(3) 0.6592(4) 0.1394(4) 0.0379(6) Uani 1 1 d . . . . . H11 H 0.250354 0.722906 0.075215 0.045 Uiso 1 1 calc R U . . . C13 C 0.2321(5) 0.4907(5) 0.2435(7) 0.0648(15) Uani 1 1 d . . . . . H13 H 0.183100 0.440791 0.249539 0.078 Uiso 1 1 calc R U . . . C12 C 0.1994(4) 0.5851(5) 0.1481(6) 0.0520(11) Uani 1 1 d . . . . . H12 H 0.128618 0.598885 0.089927 0.062 Uiso 1 1 calc R U . . . C14 C 0.3355(6) 0.4701(5) 0.3288(7) 0.0664(15) Uani 1 1 d . . . . . H14 H 0.356792 0.407799 0.394932 0.080 Uiso 1 1 calc R U . . . C9 C 0.4225(3) 0.8225(4) 0.1146(4) 0.0399(7) Uani 1 1 d . . . . . H9A H 0.372589 0.796029 0.020930 0.060 Uiso 1 1 calc R U . . . H9B H 0.390113 0.878807 0.149773 0.060 Uiso 1 1 calc R U . . . H9C H 0.480035 0.860412 0.109964 0.060 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 I1 0.02471(7) 0.04124(9) 0.03160(9) -0.01348(8) 0.00795(6) -0.00082(7) I2 0.02909(9) 0.06997(18) 0.04351(13) 0.00540(11) 0.01526(9) 0.02428(11) Cu1 0.01486(14) 0.0371(2) 0.01773(17) 0.000 0.00573(13) 0.000 C1 0.0217(9) 0.0375(12) 0.0224(11) -0.0063(9) 0.0081(8) 0.0031(9) N1 0.0206(8) 0.0359(11) 0.0196(9) -0.0067(8) 0.0066(7) -0.0007(8) O1 0.0144(6) 0.0386(10) 0.0263(9) -0.0092(7) 0.0066(6) 0.0016(6) C2 0.0182(9) 0.0360(12) 0.0216(10) -0.0045(9) 0.0075(8) 0.0019(8) C7 0.0149(7) 0.0292(10) 0.0211(9) -0.0019(8) 0.0061(7) 0.0023(7) C4 0.0194(9) 0.0441(15) 0.0289(13) -0.0001(11) 0.0096(9) 0.0089(10) C3 0.0226(10) 0.0438(15) 0.0274(12) -0.0034(11) 0.0113(9) 0.0074(10) C6 0.0162(8) 0.0331(11) 0.0229(10) -0.0045(8) 0.0057(7) 0.0013(7) C10 0.0287(12) 0.0351(13) 0.0232(11) -0.0081(10) 0.0060(9) -0.0035(10) C5 0.0152(8) 0.0428(14) 0.0269(11) -0.0023(10) 0.0052(8) 0.0051(9) C15 0.054(2) 0.0394(16) 0.043(2) 0.0021(16) 0.0081(19) -0.0045(17) C8 0.0248(10) 0.0425(14) 0.0196(10) -0.0081(10) 0.0071(9) -0.0016(10) C11 0.0292(13) 0.0438(16) 0.0330(15) -0.0109(13) 0.0084(11) -0.0051(12) C13 0.066(3) 0.059(3) 0.067(3) -0.014(2) 0.030(3) -0.033(3) C12 0.0385(19) 0.061(3) 0.051(2) -0.019(2) 0.0166(18) -0.0183(18) C14 0.077(4) 0.048(2) 0.064(3) 0.006(2) 0.026(3) -0.018(2) C9 0.0399(16) 0.0494(19) 0.0272(14) 0.0033(13) 0.0132(12) -0.0027(14) 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 O1 Cu1 O1 143.18(15) . 2_656 ? O1 Cu1 N1 101.92(10) . 2_656 ? O1 Cu1 N1 93.50(9) 2_656 2_656 ? O1 Cu1 N1 93.50(9) . . ? O1 Cu1 N1 101.92(10) 2_656 . ? N1 Cu1 N1 129.86(16) 2_656 . ? N1 C1 C2 127.3(3) . . ? N1 C1 H1 116.4 . . ? C2 C1 H1 116.4 . . ? C1 N1 C8 115.4(2) . . ? C1 N1 Cu1 120.2(2) . . ? C8 N1 Cu1 123.81(19) . . ? C7 O1 Cu1 127.25(18) . . ? C3 C2 C7 120.6(3) . . ? C3 C2 C1 116.1(2) . . ? C7 C2 C1 123.3(2) . . ? O1 C7 C6 120.2(2) . . ? O1 C7 C2 123.7(2) . . ? C6 C7 C2 116.0(2) . . ? C3 C4 C5 119.9(2) . . ? C3 C4 I2 120.9(2) . . ? C5 C4 I2 119.1(2) . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C6 C7 122.9(2) . . ? C5 C6 I1 118.8(2) . . ? C7 C6 I1 117.97(17) . . ? C11 C10 C15 118.0(4) . . ? C11 C10 C8 123.4(3) . . ? C15 C10 C8 118.5(4) . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C14 C15 C10 120.2(5) . . ? C14 C15 H15 119.9 . . ? C10 C15 H15 119.9 . . ? N1 C8 C10 110.0(3) . . ? N1 C8 C9 109.0(3) . . ? C10 C8 C9 115.7(3) . . ? N1 C8 H8 107.3 . . ? C10 C8 H8 107.3 . . ? C9 C8 H8 107.3 . . ? C10 C11 C12 121.4(5) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C14 C13 C12 120.4(5) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C12 C11 119.6(5) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C13 C14 C15 120.3(5) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 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 I1 C6 2.090(3) . ? I2 C4 2.086(3) . ? Cu1 O1 1.885(2) . ? Cu1 O1 1.885(2) 2_656 ? Cu1 N1 2.018(2) 2_656 ? Cu1 N1 2.019(2) . ? C1 N1 1.288(4) . ? C1 C2 1.442(4) . ? C1 H1 0.9300 . ? N1 C8 1.492(4) . ? O1 C7 1.295(3) . ? C2 C3 1.411(4) . ? C2 C7 1.418(4) . ? C7 C6 1.417(3) . ? C4 C3 1.376(4) . ? C4 C5 1.400(4) . ? C3 H3 0.9300 . ? C6 C5 1.384(4) . ? C10 C11 1.384(5) . ? C10 C15 1.403(6) . ? C10 C8 1.516(5) . ? C5 H5 0.9300 . ? C15 C14 1.394(8) . ? C15 H15 0.9300 . ? C8 C9 1.517(5) . ? C8 H8 0.9800 . ? C11 C12 1.387(6) . ? C11 H11 0.9300 . ? C13 C14 1.361(9) . ? C13 C12 1.380(9) . ? C13 H13 0.9300 . ? C12 H12 0.9300 . ? C14 H14 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? 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 C2 C1 N1 C8 175.0(3) . . . . ? C2 C1 N1 Cu1 -13.3(5) . . . . ? O1 Cu1 O1 C7 -135.9(3) 2_656 . . . ? N1 Cu1 O1 C7 111.3(3) 2_656 . . . ? N1 Cu1 O1 C7 -20.7(3) . . . . ? N1 C1 C2 C3 175.6(3) . . . . ? N1 C1 C2 C7 -4.7(5) . . . . ? Cu1 O1 C7 C6 -170.1(2) . . . . ? Cu1 O1 C7 C2 9.5(4) . . . . ? C3 C2 C7 O1 -172.4(3) . . . . ? C1 C2 C7 O1 7.9(5) . . . . ? C3 C2 C7 C6 7.2(4) . . . . ? C1 C2 C7 C6 -172.5(3) . . . . ? C5 C4 C3 C2 -2.9(5) . . . . ? I2 C4 C3 C2 172.5(3) . . . . ? C7 C2 C3 C4 -2.6(5) . . . . ? C1 C2 C3 C4 177.1(3) . . . . ? O1 C7 C6 C5 172.8(3) . . . . ? C2 C7 C6 C5 -6.8(4) . . . . ? O1 C7 C6 I1 -0.9(4) . . . . ? C2 C7 C6 I1 179.5(2) . . . . ? C7 C6 C5 C4 1.6(5) . . . . ? I1 C6 C5 C4 175.3(3) . . . . ? C3 C4 C5 C6 3.4(5) . . . . ? I2 C4 C5 C6 -172.1(3) . . . . ? C11 C10 C15 C14 -3.4(7) . . . . ? C8 C10 C15 C14 -179.5(5) . . . . ? C1 N1 C8 C10 123.0(3) . . . . ? Cu1 N1 C8 C10 -48.3(4) . . . . ? C1 N1 C8 C9 -109.1(3) . . . . ? Cu1 N1 C8 C9 79.6(3) . . . . ? C11 C10 C8 N1 129.8(3) . . . . ? C15 C10 C8 N1 -54.3(4) . . . . ? C11 C10 C8 C9 5.7(5) . . . . ? C15 C10 C8 C9 -178.4(3) . . . . ? C15 C10 C11 C12 1.4(6) . . . . ? C8 C10 C11 C12 177.4(4) . . . . ? C14 C13 C12 C11 0.0(9) . . . . ? C10 C11 C12 C13 0.2(7) . . . . ? C12 C13 C14 C15 -2.0(10) . . . . ? C10 C15 C14 C13 3.7(10) . . . . ?