# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C42 H38 Br Cu N5 P' _chemical_formula_sum 'C42 H38 Br Cu N5 P' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour yellow _diffrn_ambient_temperature 296(2) _chemical_formula_weight 787.19 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' P P 0.1023 0.0942 '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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.2558(4) _cell_length_b 13.1040(5) _cell_length_c 13.3930(5) _cell_angle_alpha 69.8400(10) _cell_angle_beta 79.4400(10) _cell_angle_gamma 82.6460(10) _cell_volume 1818.48(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4335 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 26.36 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.438 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 1.781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5509 _exptl_absorpt_correction_T_max 0.8147 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8Apex CCD area-detector' _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean 25 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12737 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.02 _reflns_number_total 7157 _reflns_number_gt 5682 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXTL (Bruker, 2004)' _computing_structure_refinement 'SHELXTL (Bruker, 2004)' _computing_molecular_graphics 'SHELXTL (Bruker, 2004)' _computing_publication_material 'SHELXTL (Bruker, 2004)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+0.5109P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7157 _refine_ls_number_parameters 496 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0762 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.73924(2) 0.14380(2) 0.24802(2) 0.03188(8) Uani 1 1 d . . . Cu1 Cu 0.79026(3) 0.28406(2) 0.30681(2) 0.02167(9) Uani 1 1 d . . . P1 P 0.77024(5) 0.27799(5) 0.47441(5) 0.02071(14) Uani 1 1 d . A . N13 N 0.68593(18) 0.41823(17) 0.21795(17) 0.0299(5) Uani 1 1 d . . . N11 N 0.92302(17) 0.38584(15) 0.20021(15) 0.0198(4) Uani 1 1 d . . . N12 N 0.87244(16) 0.48928(15) 0.15389(15) 0.0183(4) Uani 1 1 d . . . C13 C 0.9568(2) 0.56599(19) 0.12500(18) 0.0195(5) Uani 1 1 d . . . C21 C 0.8855(2) 0.21124(19) 0.56112(18) 0.0209(5) Uani 1 1 d . . . C14 C 0.7474(2) 0.49958(19) 0.14359(18) 0.0203(5) Uani 1 1 d . . . C15 C 0.6971(2) 0.58092(19) 0.06493(18) 0.0215(5) Uani 1 1 d . . . H15 H 0.7441 0.6318 0.0109 0.026 Uiso 1 1 calc R . . C116 C 1.0994(2) 0.19895(19) 0.24760(19) 0.0238(6) Uani 1 1 d . . . H116 H 1.0309 0.1893 0.2230 0.029 Uiso 1 1 calc R . . C132 C 1.0085(2) 0.7483(2) -0.00096(19) 0.0235(5) Uani 1 1 d . . . H132 H 1.0753 0.7151 -0.0330 0.028 Uiso 1 1 calc R . . C131 C 0.9301(2) 0.68484(19) 0.08406(18) 0.0196(5) Uani 1 1 d . . . C11 C 1.0394(2) 0.39793(19) 0.19745(18) 0.0196(5) Uani 1 1 d . . . C12 C 1.0640(2) 0.50865(19) 0.15123(19) 0.0233(6) Uani 1 1 d . . . H12 H 1.1385 0.5374 0.1406 0.028 Uiso 1 1 calc R . . C111 C 1.1226(2) 0.30242(19) 0.24213(18) 0.0200(5) Uani 1 1 d . . . N15 N 0.50674(18) 0.66301(18) 0.00124(17) 0.0301(5) Uani 1 1 d . . . C136 C 0.8320(2) 0.7363(2) 0.1323(2) 0.0250(6) Uani 1 1 d . . . H136 H 0.7804 0.6951 0.1909 0.030 Uiso 1 1 calc R . . C22 C 0.9749(2) 0.1404(2) 0.5296(2) 0.0290(6) Uani 1 1 d . . . H22 H 0.9765 0.1289 0.4647 0.035 Uiso 1 1 calc R . . C42 C 0.5670(2) 0.1638(2) 0.5145(2) 0.0272(6) Uani 1 1 d . A . H42 H 0.5919 0.1639 0.4443 0.033 Uiso 1 1 calc R . . C24 C 1.0606(2) 0.1035(2) 0.6912(2) 0.0295(6) Uani 1 1 d . . . H24 H 1.1189 0.0675 0.7347 0.035 Uiso 1 1 calc R . . C16 C 0.5700(2) 0.5845(2) 0.0693(2) 0.0269(6) Uani 1 1 d . . . N14 N 0.50648(19) 0.50357(19) 0.14445(19) 0.0422(7) Uani 1 1 d . . . C26 C 0.8860(2) 0.2289(2) 0.6580(2) 0.0301(6) Uani 1 1 d . . . H26 H 0.8280 0.2777 0.6791 0.036 Uiso 1 1 calc R . . C113 C 1.3012(2) 0.2249(2) 0.3243(2) 0.0339(7) Uani 1 1 d . . . H113 H 1.3683 0.2336 0.3512 0.041 Uiso 1 1 calc R . . C115 C 1.1779(2) 0.1098(2) 0.2896(2) 0.0288(6) Uani 1 1 d . . . H115 H 1.1627 0.0410 0.2914 0.035 Uiso 1 1 calc R . . C114 C 1.2781(2) 0.1224(2) 0.3287(2) 0.0308(6) Uani 1 1 d . . . H114 H 1.3299 0.0623 0.3577 0.037 Uiso 1 1 calc R . . C23 C 1.0619(2) 0.0869(2) 0.5946(2) 0.0334(7) Uani 1 1 d . . . H23 H 1.1214 0.0395 0.5730 0.040 Uiso 1 1 calc R . . C112 C 1.2252(2) 0.3149(2) 0.2803(2) 0.0290(6) Uani 1 1 d . . . H112 H 1.2427 0.3838 0.2761 0.035 Uiso 1 1 calc R . . C43 C 0.4648(2) 0.1092(2) 0.5734(2) 0.0346(7) Uani 1 1 d D . . C41 C 0.6315(2) 0.2165(3) 0.5552(2) 0.0360(7) Uani 1 1 d . . . C134 C 0.8883(3) 0.9104(2) 0.0076(2) 0.0338(7) Uani 1 1 d . . . H134 H 0.8734 0.9856 -0.0193 0.041 Uiso 1 1 calc R . . C161 C 0.5549(2) 0.7666(2) -0.0682(2) 0.0347(7) Uani 1 1 d . . . H16A H 0.5262 0.7887 -0.1371 0.042 Uiso 1 1 calc R . . H16B H 0.6427 0.7582 -0.0807 0.042 Uiso 1 1 calc R . . C135 C 0.8108(2) 0.8490(2) 0.0932(2) 0.0299(6) Uani 1 1 d . . . H135 H 0.7444 0.8830 0.1249 0.036 Uiso 1 1 calc R . . C133 C 0.9878(2) 0.8606(2) -0.0382(2) 0.0315(6) Uani 1 1 d . . . H133 H 1.0414 0.9025 -0.0944 0.038 Uiso 1 1 calc R . . C25 C 0.9720(3) 0.1742(2) 0.7227(2) 0.0330(6) Uani 1 1 d . . . H25 H 0.9704 0.1850 0.7880 0.040 Uiso 1 1 calc R . . C17 C 0.5680(2) 0.4259(2) 0.2101(2) 0.0451(9) Uani 1 1 d . . . H17 H 0.5241 0.3685 0.2575 0.054 Uiso 1 1 calc R . . C165 C 0.3731(2) 0.6704(2) 0.0186(2) 0.0385(7) Uani 1 1 d . . . H16C H 0.3440 0.5995 0.0613 0.046 Uiso 1 1 calc R . . H16D H 0.3437 0.6932 -0.0500 0.046 Uiso 1 1 calc R . . C164 C 0.3265(3) 0.7511(3) 0.0757(3) 0.0529(9) Uani 1 1 d . . . H16E H 0.3510 0.7252 0.1465 0.064 Uiso 1 1 calc R . . H16F H 0.2387 0.7580 0.0847 0.064 Uiso 1 1 calc R . . C162 C 0.5145(3) 0.8527(3) -0.0156(3) 0.0550(9) Uani 1 1 d . . . H16G H 0.5417 0.9225 -0.0641 0.066 Uiso 1 1 calc R . . H16H H 0.5506 0.8345 0.0493 0.066 Uiso 1 1 calc R . . C163 C 0.3752(3) 0.8611(3) 0.0126(3) 0.0606(10) Uani 1 1 d . . . H16I H 0.3515 0.9097 0.0546 0.073 Uiso 1 1 calc R . . H16J H 0.3399 0.8921 -0.0532 0.073 Uiso 1 1 calc R . . C44B C 0.4157(8) 0.1343(7) 0.6715(8) 0.047(2) Uani 0.50 1 d P A 1 H44B H 0.3496 0.0985 0.7160 0.056 Uiso 0.50 1 calc PR A 1 C46B C 0.5700(5) 0.2598(6) 0.6398(5) 0.0455(16) Uani 0.50 1 d P A 1 H46B H 0.5992 0.3170 0.6522 0.055 Uiso 0.50 1 calc PR A 1 C45B C 0.4656(6) 0.2111(7) 0.7007(5) 0.055(2) Uani 0.50 1 d P A 1 H45B H 0.4287 0.2294 0.7609 0.066 Uiso 0.50 1 calc PR A 1 C31 C 0.7592(2) 0.4164(2) 0.4790(2) 0.0300(6) Uani 1 1 d . . . C32 C 0.8565(3) 0.4743(3) 0.4410(3) 0.0728(13) Uani 1 1 d . A . H32 H 0.9288 0.4413 0.4168 0.087 Uiso 1 1 calc R . . C45A C 0.5124(5) 0.1170(5) 0.7291(4) 0.0302(13) Uani 0.50 1 d P A 2 H45A H 0.4952 0.1003 0.8034 0.036 Uiso 0.50 1 calc PR A 2 C46A C 0.6123(5) 0.1762(5) 0.6724(4) 0.0261(12) Uani 0.50 1 d P A 2 H46A H 0.6670 0.1901 0.7097 0.031 Uiso 0.50 1 calc PR A 2 C44A C 0.4399(8) 0.0835(6) 0.6774(8) 0.0285(18) Uani 0.50 1 d P A 2 H44A H 0.3740 0.0432 0.7155 0.034 Uiso 0.50 1 calc PR A 2 C34 C 0.7575(4) 0.6351(3) 0.4679(4) 0.0700(12) Uani 1 1 d D . . C33 C 0.8539(4) 0.5820(3) 0.4363(3) 0.0718(13) Uani 1 1 d . A . H33 H 0.9250 0.6179 0.4092 0.086 Uiso 1 1 calc R . . C36A C 0.6604(5) 0.4499(5) 0.5518(6) 0.0362(14) Uani 0.50 1 d P A 2 H36A H 0.6031 0.4022 0.5960 0.043 Uiso 0.50 1 calc PR A 2 C35A C 0.6567(6) 0.5554(6) 0.5516(7) 0.0525(18) Uani 0.50 1 d P A 2 H35A H 0.5981 0.5807 0.5979 0.063 Uiso 0.50 1 calc PR A 2 C36B C 0.6608(6) 0.4921(6) 0.4619(8) 0.058(2) Uani 0.50 1 d P A 1 H36B H 0.5892 0.4706 0.4526 0.070 Uiso 0.50 1 calc PR A 1 C35B C 0.6649(6) 0.5984(5) 0.4582(7) 0.068(2) Uani 0.50 1 d P A 1 H35B H 0.5952 0.6448 0.4479 0.082 Uiso 0.50 1 calc PR A 1 H43 H 0.4262 0.0655 0.5363 0.082 Uiso 1 1 d RD . . H34 H 0.7644 0.7176 0.4615 0.082 Uiso 1 1 d RD . . 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 Br1 0.03332(16) 0.03383(16) 0.03537(16) -0.01780(12) -0.01416(12) 0.00415(12) Cu1 0.02075(16) 0.02079(16) 0.02010(16) -0.00277(12) -0.00275(12) -0.00113(12) P1 0.0171(3) 0.0229(3) 0.0238(3) -0.0098(3) -0.0013(2) -0.0041(3) N13 0.0176(11) 0.0258(12) 0.0331(12) 0.0059(10) -0.0025(9) -0.0007(9) N11 0.0168(10) 0.0190(11) 0.0206(10) -0.0033(8) -0.0033(8) 0.0016(8) N12 0.0151(10) 0.0182(10) 0.0193(10) -0.0031(8) -0.0042(8) 0.0008(8) C13 0.0178(12) 0.0229(13) 0.0177(12) -0.0059(10) -0.0022(9) -0.0040(10) C21 0.0220(13) 0.0186(12) 0.0201(12) -0.0032(10) -0.0010(10) -0.0065(10) C14 0.0150(12) 0.0217(13) 0.0222(12) -0.0053(10) -0.0020(9) -0.0009(10) C15 0.0177(12) 0.0227(13) 0.0196(12) -0.0009(10) -0.0024(10) -0.0033(10) C116 0.0181(13) 0.0261(14) 0.0259(13) -0.0070(11) -0.0028(10) -0.0022(10) C132 0.0229(13) 0.0265(14) 0.0225(13) -0.0085(11) -0.0050(10) -0.0035(11) C131 0.0187(12) 0.0203(12) 0.0209(12) -0.0056(10) -0.0089(10) -0.0005(10) C11 0.0166(12) 0.0227(13) 0.0186(12) -0.0056(10) -0.0035(9) 0.0003(10) C12 0.0181(13) 0.0251(13) 0.0247(13) -0.0049(11) -0.0019(10) -0.0048(10) C111 0.0142(12) 0.0229(13) 0.0199(12) -0.0050(10) -0.0012(9) 0.0021(10) N15 0.0166(11) 0.0352(13) 0.0301(12) 0.0011(10) -0.0079(9) 0.0015(9) C136 0.0223(13) 0.0285(14) 0.0246(13) -0.0087(11) -0.0051(10) -0.0015(11) C22 0.0269(14) 0.0329(15) 0.0272(14) -0.0109(12) -0.0023(11) -0.0015(12) C42 0.0234(14) 0.0245(14) 0.0314(15) -0.0086(11) 0.0009(11) -0.0027(11) C24 0.0259(14) 0.0266(14) 0.0322(15) -0.0009(12) -0.0093(11) -0.0058(11) C16 0.0193(13) 0.0299(15) 0.0272(14) -0.0038(11) -0.0045(10) -0.0012(11) N14 0.0149(11) 0.0405(14) 0.0505(15) 0.0116(12) -0.0046(10) -0.0036(10) C26 0.0361(16) 0.0265(14) 0.0268(14) -0.0095(11) -0.0057(12) 0.0039(12) C113 0.0205(14) 0.0375(17) 0.0399(16) -0.0045(13) -0.0120(12) -0.0016(12) C115 0.0293(15) 0.0223(14) 0.0307(14) -0.0059(11) -0.0013(11) -0.0004(11) C114 0.0239(14) 0.0265(15) 0.0315(15) 0.0008(12) -0.0039(11) 0.0062(11) C23 0.0245(14) 0.0336(16) 0.0407(17) -0.0119(13) -0.0053(12) 0.0034(12) C112 0.0227(14) 0.0268(14) 0.0362(15) -0.0066(12) -0.0099(11) 0.0000(11) C43 0.0247(15) 0.0263(15) 0.0485(19) -0.0084(13) -0.0020(13) -0.0031(11) C41 0.0256(15) 0.063(2) 0.0256(14) -0.0200(14) 0.0027(11) -0.0186(14) C134 0.0389(17) 0.0191(14) 0.0481(17) -0.0078(12) -0.0256(14) -0.0002(12) C161 0.0282(15) 0.0363(16) 0.0289(15) 0.0049(12) -0.0095(11) -0.0008(12) C135 0.0224(14) 0.0317(15) 0.0440(16) -0.0211(13) -0.0149(12) 0.0072(11) C133 0.0372(16) 0.0239(14) 0.0304(15) -0.0006(11) -0.0091(12) -0.0090(12) C25 0.0438(17) 0.0309(15) 0.0246(14) -0.0083(12) -0.0083(12) -0.0011(13) C17 0.0188(14) 0.0391(17) 0.0536(19) 0.0154(15) -0.0038(13) -0.0068(12) C165 0.0193(14) 0.0503(19) 0.0360(16) 0.0000(14) -0.0108(12) 0.0021(13) C164 0.0233(16) 0.099(3) 0.0414(18) -0.0323(19) -0.0117(13) 0.0131(17) C162 0.047(2) 0.052(2) 0.078(3) -0.0283(19) -0.0310(18) 0.0016(16) C163 0.046(2) 0.074(3) 0.092(3) -0.061(2) -0.0375(19) 0.0236(18) C44B 0.019(4) 0.072(7) 0.037(4) -0.001(6) 0.000(3) -0.014(5) C46B 0.030(3) 0.076(5) 0.040(4) -0.031(4) 0.001(3) -0.014(3) C45B 0.027(3) 0.105(6) 0.038(4) -0.035(4) 0.010(3) -0.018(4) C31 0.0270(14) 0.0296(15) 0.0427(16) -0.0197(13) -0.0173(12) 0.0051(12) C32 0.063(2) 0.0334(19) 0.108(3) -0.029(2) 0.042(2) -0.0190(17) C45A 0.025(3) 0.046(4) 0.018(3) -0.010(2) 0.007(2) -0.013(3) C46A 0.020(3) 0.038(3) 0.023(3) -0.011(2) -0.002(2) -0.011(2) C44A 0.019(4) 0.022(4) 0.039(4) -0.003(4) -0.002(3) -0.004(3) C34 0.064(3) 0.040(2) 0.136(4) -0.052(2) -0.056(3) 0.0148(19) C33 0.088(3) 0.0307(19) 0.086(3) -0.0149(18) 0.023(2) -0.032(2) C36A 0.027(3) 0.028(3) 0.057(4) -0.022(3) 0.001(3) -0.005(2) C35A 0.047(4) 0.045(4) 0.075(5) -0.038(4) 0.002(4) -0.003(3) C36B 0.029(4) 0.041(4) 0.116(7) -0.038(4) -0.022(4) 0.002(3) C35B 0.044(4) 0.027(4) 0.141(8) -0.042(5) -0.010(5) 0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Br1 Cu1 2.4003(4) . ? Cu1 N13 2.104(2) . ? Cu1 N11 2.1133(18) . ? Cu1 P1 2.1890(7) . ? P1 C31 1.823(3) . ? P1 C21 1.832(3) . ? P1 C41 1.833(2) . ? N13 C17 1.339(3) . ? N13 C14 1.346(3) . ? N11 C11 1.332(3) . ? N11 N12 1.378(3) . ? N12 C13 1.380(3) . ? N12 C14 1.424(3) . ? C13 C12 1.373(3) . ? C13 C131 1.473(3) . ? C21 C22 1.388(3) . ? C21 C26 1.395(4) . ? C14 C15 1.363(3) . ? C15 C16 1.416(3) . ? C116 C111 1.388(3) . ? C116 C115 1.389(3) . ? C132 C133 1.384(3) . ? C132 C131 1.390(3) . ? C131 C136 1.393(3) . ? C11 C12 1.409(3) . ? C11 C111 1.480(3) . ? C111 C112 1.394(3) . ? N15 C16 1.342(3) . ? N15 C161 1.461(3) . ? N15 C165 1.475(3) . ? C136 C135 1.391(4) . ? C22 C23 1.387(4) . ? C42 C41 1.354(4) . ? C42 C43 1.395(3) . ? C24 C25 1.381(4) . ? C24 C23 1.381(4) . ? C16 N14 1.358(3) . ? N14 C17 1.309(3) . ? C26 C25 1.380(4) . ? C113 C114 1.380(4) . ? C113 C112 1.384(4) . ? C115 C114 1.377(4) . ? C43 C44A 1.300(10) . ? C43 C44B 1.457(11) . ? C41 C46A 1.458(6) . ? C41 C46B 1.463(7) . ? C134 C133 1.376(4) . ? C134 C135 1.379(4) . ? C161 C162 1.508(4) . ? C165 C164 1.498(4) . ? C164 C163 1.512(5) . ? C162 C163 1.542(4) . ? C44B C45B 1.407(13) . ? C46B C45B 1.391(8) . ? C31 C32 1.333(4) . ? C31 C36B 1.385(7) . ? C31 C36A 1.468(6) . ? C32 C33 1.388(5) . ? C45A C44A 1.359(11) . ? C45A C46A 1.395(7) . ? C34 C35B 1.247(7) . ? C34 C33 1.297(5) . ? C34 C35A 1.632(8) . ? C36A C35A 1.377(8) . ? C36B C35B 1.383(8) . ? 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 N13 Cu1 N11 77.08(7) . . ? N13 Cu1 P1 110.68(7) . . ? N11 Cu1 P1 115.02(6) . . ? N13 Cu1 Br1 100.28(7) . . ? N11 Cu1 Br1 115.18(6) . . ? P1 Cu1 Br1 125.31(2) . . ? C31 P1 C21 101.49(12) . . ? C31 P1 C41 106.21(13) . . ? C21 P1 C41 102.87(12) . . ? C31 P1 Cu1 109.29(9) . . ? C21 P1 Cu1 122.81(8) . . ? C41 P1 Cu1 112.61(9) . . ? C17 N13 C14 113.6(2) . . ? C17 N13 Cu1 128.52(17) . . ? C14 N13 Cu1 116.53(16) . . ? C11 N11 N12 105.44(18) . . ? C11 N11 Cu1 136.09(16) . . ? N12 N11 Cu1 110.75(13) . . ? N11 N12 C13 111.27(18) . . ? N11 N12 C14 117.20(18) . . ? C13 N12 C14 131.53(19) . . ? C12 C13 N12 105.8(2) . . ? C12 C13 C131 128.8(2) . . ? N12 C13 C131 125.2(2) . . ? C22 C21 C26 118.9(2) . . ? C22 C21 P1 118.93(19) . . ? C26 C21 P1 122.14(19) . . ? N13 C14 C15 124.1(2) . . ? N13 C14 N12 112.4(2) . . ? C15 C14 N12 123.5(2) . . ? C14 C15 C16 116.9(2) . . ? C111 C116 C115 120.3(2) . . ? C133 C132 C131 120.4(2) . . ? C132 C131 C136 118.9(2) . . ? C132 C131 C13 119.4(2) . . ? C136 C131 C13 121.6(2) . . ? N11 C11 C12 110.6(2) . . ? N11 C11 C111 120.5(2) . . ? C12 C11 C111 128.8(2) . . ? C13 C12 C11 106.8(2) . . ? C116 C111 C112 118.9(2) . . ? C116 C111 C11 120.7(2) . . ? C112 C111 C11 120.4(2) . . ? C16 N15 C161 123.4(2) . . ? C16 N15 C165 121.2(2) . . ? C161 N15 C165 111.7(2) . . ? C135 C136 C131 120.3(2) . . ? C23 C22 C21 120.3(3) . . ? C41 C42 C43 122.9(3) . . ? C25 C24 C23 119.5(3) . . ? N15 C16 N14 116.7(2) . . ? N15 C16 C15 123.8(2) . . ? N14 C16 C15 119.5(2) . . ? C17 N14 C16 116.9(2) . . ? C25 C26 C21 120.3(2) . . ? C114 C113 C112 120.6(3) . . ? C114 C115 C116 120.5(2) . . ? C115 C114 C113 119.5(2) . . ? C24 C23 C22 120.4(3) . . ? C113 C112 C111 120.2(2) . . ? C44A C43 C42 122.2(5) . . ? C44A C43 C44B 27.3(4) . . ? C42 C43 C44B 114.6(4) . . ? C42 C41 C46A 111.6(3) . . ? C42 C41 C46B 118.9(3) . . ? C46A C41 C46B 44.6(3) . . ? C42 C41 P1 119.4(2) . . ? C46A C41 P1 123.2(3) . . ? C46B C41 P1 117.6(3) . . ? C133 C134 C135 120.1(2) . . ? N15 C161 C162 109.8(2) . . ? C134 C135 C136 120.0(2) . . ? C134 C133 C132 120.2(2) . . ? C26 C25 C24 120.5(3) . . ? N14 C17 N13 128.6(2) . . ? N15 C165 C164 109.5(2) . . ? C165 C164 C163 110.6(3) . . ? C161 C162 C163 110.4(3) . . ? C164 C163 C162 111.8(3) . . ? C45B C44B C43 121.9(7) . . ? C45B C46B C41 116.6(6) . . ? C46B C45B C44B 120.1(7) . . ? C32 C31 C36B 105.4(4) . . ? C32 C31 C36A 119.0(3) . . ? C36B C31 C36A 46.9(4) . . ? C32 C31 P1 118.9(2) . . ? C36B C31 P1 127.0(3) . . ? C36A C31 P1 119.4(3) . . ? C31 C32 C33 122.4(3) . . ? C44A C45A C46A 121.0(6) . . ? C45A C46A C41 120.4(4) . . ? C43 C44A C45A 118.4(7) . . ? C35B C34 C33 110.2(4) . . ? C35B C34 C35A 45.7(5) . . ? C33 C34 C35A 113.1(4) . . ? C34 C33 C32 123.3(3) . . ? C35A C36A C31 116.8(5) . . ? C36A C35A C34 118.3(5) . . ? C35B C36B C31 122.6(6) . . ? C34 C35B C36B 123.3(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.533 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 915216' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C42 H38 Cl Cu N5 P' _chemical_formula_sum 'C42 H38 Cl Cu N5 P' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour yellow _diffrn_ambient_temperature 150(2) _chemical_formula_weight 742.73 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' Cl Cl 0.1484 0.1585 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1677(4) _cell_length_b 13.1184(7) _cell_length_c 13.3150(7) _cell_angle_alpha 69.3970(10) _cell_angle_beta 79.4040(10) _cell_angle_gamma 82.5140(10) _cell_volume 1790.22(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4151 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 26.35 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.768 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8312 _exptl_absorpt_correction_T_max 0.8935 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8Apex CCD area-detector' _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean 25 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 10358 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 26.37 _reflns_number_total 7270 _reflns_number_gt 5156 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXTL (Bruker, 2004)' _computing_structure_refinement 'SHELXTL (Bruker, 2004)' _computing_molecular_graphics 'SHELXTL (Bruker, 2004)' _computing_publication_material 'SHELXTL (Bruker, 2004)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+0.6302P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7270 _refine_ls_number_parameters 486 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0799 _refine_ls_wR_factor_gt 0.0756 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.78898(3) 0.27941(2) 0.30482(2) 0.01874(8) Uani 1 1 d . . . Cl1 Cl 0.74436(5) 0.14802(4) 0.24533(4) 0.02356(13) Uani 1 1 d . . . P1 P 0.77044(5) 0.27214(4) 0.47376(4) 0.01803(13) Uani 1 1 d . A . N11 N 0.92230(17) 0.38448(13) 0.19837(13) 0.0171(4) Uani 1 1 d . . . N12 N 0.87025(16) 0.48817(13) 0.15269(13) 0.0163(4) Uani 1 1 d . . . N13 N 0.68226(17) 0.41654(13) 0.21562(14) 0.0213(4) Uani 1 1 d . . . N14 N 0.50132(18) 0.50323(15) 0.14140(16) 0.0300(5) Uani 1 1 d . . . N15 N 0.50248(18) 0.66484(15) -0.00221(14) 0.0250(4) Uani 1 1 d . . . C11 C 1.0384(2) 0.39604(16) 0.19786(16) 0.0180(4) Uani 1 1 d . . . C12 C 1.0630(2) 0.50746(16) 0.15240(16) 0.0202(5) Uani 1 1 d . . . H12 H 1.1393 0.5368 0.1427 0.024 Uiso 1 1 calc R . . C13 C 0.9553(2) 0.56497(16) 0.12506(16) 0.0176(4) Uani 1 1 d . . . C14 C 0.7453(2) 0.49823(16) 0.14178(16) 0.0170(4) Uani 1 1 d . . . C15 C 0.6943(2) 0.58148(16) 0.06276(16) 0.0187(5) Uani 1 1 d . . . H15 H 0.7424 0.6346 0.0079 0.022 Uiso 1 1 calc R . . C16 C 0.5673(2) 0.58468(17) 0.06657(17) 0.0211(5) Uani 1 1 d . . . C17 C 0.5646(2) 0.42415(18) 0.2078(2) 0.0316(6) Uani 1 1 d . . . H17 H 0.5197 0.3649 0.2563 0.038 Uiso 1 1 calc R . . C21 C 0.8882(2) 0.20686(16) 0.55994(16) 0.0181(4) Uani 1 1 d . . . C22 C 0.9771(2) 0.13472(18) 0.52954(17) 0.0246(5) Uani 1 1 d . . . H22 H 0.9777 0.1218 0.4636 0.029 Uiso 1 1 calc R . . C23 C 1.0658(2) 0.08102(18) 0.59517(19) 0.0290(5) Uani 1 1 d . . . H23 H 1.1266 0.0318 0.5737 0.035 Uiso 1 1 calc R . . C24 C 1.0655(2) 0.09918(18) 0.69111(18) 0.0267(5) Uani 1 1 d . . . H24 H 1.1255 0.0619 0.7360 0.032 Uiso 1 1 calc R . . C25 C 0.9778(2) 0.17158(18) 0.72225(18) 0.0269(5) Uani 1 1 d . . . H25 H 0.9776 0.1841 0.7884 0.032 Uiso 1 1 calc R . . C26 C 0.8905(2) 0.22570(17) 0.65653(17) 0.0244(5) Uani 1 1 d . . . H26 H 0.8313 0.2763 0.6774 0.029 Uiso 1 1 calc R . . C31 C 0.7576(2) 0.41020(18) 0.47988(18) 0.0257(5) Uani 1 1 d D . . C41 C 0.6326(2) 0.20707(19) 0.55594(17) 0.0266(5) Uani 1 1 d . . . C42 C 0.5643(2) 0.15995(16) 0.51039(17) 0.0220(5) Uani 1 1 d . A 1 H42 H 0.5870 0.1660 0.4363 0.026 Uiso 1 1 calc R A 1 C111 C 1.1228(2) 0.30086(16) 0.24232(16) 0.0186(4) Uani 1 1 d . . . C112 C 1.2238(2) 0.31264(18) 0.28335(18) 0.0264(5) Uani 1 1 d . . . H112 H 1.2403 0.3828 0.2810 0.032 Uiso 1 1 calc R . . C113 C 1.3009(2) 0.22199(19) 0.32791(19) 0.0302(6) Uani 1 1 d . . . H113 H 1.3692 0.2305 0.3568 0.036 Uiso 1 1 calc R . . C114 C 1.2792(2) 0.11979(18) 0.33060(18) 0.0279(5) Uani 1 1 d . . . H114 H 1.3324 0.0582 0.3610 0.033 Uiso 1 1 calc R . . C115 C 1.1794(2) 0.10755(17) 0.28880(17) 0.0252(5) Uani 1 1 d . . . H115 H 1.1650 0.0376 0.2891 0.030 Uiso 1 1 calc R . . C116 C 1.1002(2) 0.19712(17) 0.24637(16) 0.0219(5) Uani 1 1 d . . . H116 H 1.0304 0.1878 0.2200 0.026 Uiso 1 1 calc R . . C131 C 0.9286(2) 0.68440(16) 0.08393(16) 0.0172(4) Uani 1 1 d . . . C132 C 1.0100(2) 0.74772(17) -0.00055(16) 0.0208(5) Uani 1 1 d . . . H132 H 1.0792 0.7134 -0.0323 0.025 Uiso 1 1 calc R . . C133 C 0.9902(2) 0.86046(17) -0.03833(18) 0.0266(5) Uani 1 1 d . . . H133 H 1.0462 0.9032 -0.0956 0.032 Uiso 1 1 calc R . . C134 C 0.8894(2) 0.91080(17) 0.00708(18) 0.0270(5) Uani 1 1 d . . . H134 H 0.8749 0.9879 -0.0202 0.032 Uiso 1 1 calc R . . C135 C 0.8093(2) 0.84871(18) 0.09245(19) 0.0257(5) Uani 1 1 d . . . H135 H 0.7406 0.8835 0.1242 0.031 Uiso 1 1 calc R . . C136 C 0.8291(2) 0.73591(17) 0.13174(17) 0.0214(5) Uani 1 1 d . . . H136 H 0.7749 0.6938 0.1912 0.026 Uiso 1 1 calc R . . C161 C 0.5528(2) 0.76813(19) -0.07197(18) 0.0313(6) Uani 1 1 d . . . H16C H 0.5234 0.7922 -0.1430 0.038 Uiso 1 1 calc R . . H16D H 0.6431 0.7584 -0.0846 0.038 Uiso 1 1 calc R . . C162 C 0.5131(3) 0.8536(2) -0.0179(3) 0.0515(8) Uani 1 1 d . . . H16G H 0.5421 0.9249 -0.0672 0.062 Uiso 1 1 calc R . . H16H H 0.5505 0.8332 0.0491 0.062 Uiso 1 1 calc R . . C163 C 0.3742(3) 0.8639(3) 0.0105(3) 0.0559(9) Uani 1 1 d . . . H16I H 0.3513 0.9128 0.0542 0.067 Uiso 1 1 calc R . . H16J H 0.3377 0.8973 -0.0572 0.067 Uiso 1 1 calc R . . C164 C 0.3230(3) 0.7537(3) 0.0739(2) 0.0465(8) Uani 1 1 d . . . H16E H 0.3481 0.7257 0.1469 0.056 Uiso 1 1 calc R . . H16F H 0.2327 0.7620 0.0830 0.056 Uiso 1 1 calc R . . C165 C 0.3687(2) 0.6733(2) 0.01541(19) 0.0318(6) Uani 1 1 d . . . H16A H 0.3381 0.6008 0.0591 0.038 Uiso 1 1 calc R . . H16B H 0.3381 0.6979 -0.0552 0.038 Uiso 1 1 calc R . . C32A C 0.8567(3) 0.4697(2) 0.4346(2) 0.0502(8) Uani 0.707(7) 1 d PD B 1 H32A H 0.9314 0.4357 0.4104 0.060 Uiso 1 1 calc R B 1 C33A C 0.8503(10) 0.5796(5) 0.4232(6) 0.0476(16) Uani 0.707(7) 1 d PD B 1 H33A H 0.9143 0.6242 0.3805 0.057 Uiso 0.707(7) 1 calc PR B 1 C34A C 0.7497(9) 0.6217(9) 0.4747(15) 0.057(2) Uani 0.707(7) 1 d PD B 1 H34A H 0.7472 0.6956 0.4710 0.068 Uiso 0.707(7) 1 calc PR B 1 C35A C 0.6500(5) 0.5607(4) 0.5328(6) 0.0661(19) Uani 0.707(7) 1 d PD B 1 H35A H 0.5818 0.5922 0.5687 0.079 Uiso 0.707(7) 1 calc PR B 1 C36A C 0.6531(4) 0.4523(4) 0.5370(5) 0.0462(13) Uani 0.707(7) 1 d PD B 1 H36A H 0.5877 0.4080 0.5765 0.055 Uiso 0.707(7) 1 calc PR B 1 C43A C 0.4631(2) 0.10375(18) 0.57008(19) 0.0271(5) Uani 0.684(10) 1 d P A 1 H43A H 0.4130 0.0804 0.5331 0.033 Uiso 1 1 calc R A 1 C44A C 0.4329(4) 0.0808(5) 0.6776(4) 0.0250(10) Uani 0.684(10) 1 d P A 1 H44A H 0.3647 0.0401 0.7171 0.030 Uiso 0.684(10) 1 calc PR A 1 C45A C 0.5060(5) 0.1194(5) 0.7287(3) 0.0349(13) Uani 0.684(10) 1 d P A 1 H45A H 0.4875 0.1052 0.8047 0.042 Uiso 0.684(10) 1 calc PR A 1 C46A C 0.6052(5) 0.1783(5) 0.6699(3) 0.0329(12) Uani 0.684(10) 1 d P A 1 H46A H 0.6564 0.2000 0.7073 0.039 Uiso 0.684(10) 1 calc PR A 1 C32B C 0.8567(3) 0.4697(2) 0.4346(2) 0.0502(8) Uani 0.293(7) 1 d PD B 2 C33B C 0.871(3) 0.5711(14) 0.4494(16) 0.0476(16) Uani 0.293(7) 1 d PD B 2 H33B H 0.9483 0.5892 0.4546 0.057 Uiso 0.293(7) 1 calc PR B 2 C34B C 0.769(2) 0.641(3) 0.456(4) 0.057(2) Uani 0.293(7) 1 d PD B 2 H34B H 0.7709 0.7130 0.4554 0.068 Uiso 0.293(7) 1 calc PR B 2 C35B C 0.6668(15) 0.5928(11) 0.4624(14) 0.0661(19) Uani 0.293(7) 1 d PD B 2 H35B H 0.5917 0.6363 0.4615 0.079 Uiso 0.293(7) 1 calc PR B 2 C36B C 0.6631(11) 0.4847(9) 0.4705(12) 0.0462(13) Uani 0.293(7) 1 d PD B 2 H36B H 0.5863 0.4617 0.4692 0.055 Uiso 0.293(7) 1 calc PR B 2 C43B C 0.4631(2) 0.10375(18) 0.57008(19) 0.0271(5) Uani 0.316(10) 1 d P A 2 C44B C 0.4180(11) 0.1240(9) 0.6721(10) 0.0250(10) Uani 0.316(10) 1 d P A 2 H44B H 0.3479 0.0895 0.7165 0.030 Uiso 0.316(10) 1 calc PR A 2 C45B C 0.4734(10) 0.1914(14) 0.7063(8) 0.048(4) Uani 0.316(10) 1 d P A 2 H45B H 0.4403 0.2017 0.7734 0.058 Uiso 0.316(10) 1 calc PR A 2 C46B C 0.5742(9) 0.2436(13) 0.6466(8) 0.034(3) Uani 0.316(10) 1 d P A 2 H46B H 0.6045 0.2997 0.6626 0.041 Uiso 0.316(10) 1 calc PR A 2 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 Cu1 0.01987(18) 0.01694(14) 0.01768(14) -0.00316(10) -0.00300(10) -0.00260(10) Cl1 0.0282(4) 0.0205(3) 0.0254(3) -0.0102(2) -0.0090(2) 0.0006(2) P1 0.0174(3) 0.0187(3) 0.0192(3) -0.0073(2) -0.0030(2) -0.0025(2) N11 0.0180(11) 0.0144(8) 0.0176(8) -0.0032(7) -0.0052(7) 0.0012(7) N12 0.0146(11) 0.0137(8) 0.0183(8) -0.0023(7) -0.0040(7) 0.0003(7) N13 0.0138(12) 0.0181(9) 0.0259(10) -0.0005(7) -0.0013(8) -0.0018(7) N14 0.0133(13) 0.0276(11) 0.0388(11) 0.0027(9) -0.0066(9) -0.0017(8) N15 0.0163(12) 0.0272(10) 0.0261(10) -0.0022(8) -0.0058(8) 0.0014(8) C11 0.0154(14) 0.0196(10) 0.0183(10) -0.0058(8) -0.0025(8) -0.0009(8) C12 0.0157(14) 0.0201(11) 0.0229(11) -0.0041(9) -0.0034(9) -0.0031(8) C13 0.0166(14) 0.0181(10) 0.0165(10) -0.0032(8) -0.0017(8) -0.0041(8) C14 0.0132(13) 0.0180(10) 0.0204(10) -0.0078(8) -0.0006(8) -0.0020(8) C15 0.0174(14) 0.0191(10) 0.0179(10) -0.0037(8) -0.0026(8) -0.0023(8) C16 0.0190(15) 0.0222(11) 0.0216(11) -0.0068(9) -0.0039(9) 0.0000(9) C17 0.0183(16) 0.0251(12) 0.0390(14) 0.0049(10) -0.0016(11) -0.0068(9) C21 0.0176(13) 0.0166(10) 0.0179(10) -0.0026(8) -0.0008(8) -0.0058(8) C22 0.0232(15) 0.0277(12) 0.0221(11) -0.0083(9) -0.0016(9) -0.0020(9) C23 0.0232(16) 0.0267(12) 0.0336(13) -0.0084(10) -0.0023(10) 0.0030(9) C24 0.0249(15) 0.0235(12) 0.0277(12) -0.0001(9) -0.0094(10) -0.0043(9) C25 0.0299(16) 0.0282(12) 0.0237(12) -0.0075(10) -0.0087(10) -0.0028(10) C26 0.0271(15) 0.0223(11) 0.0236(11) -0.0076(9) -0.0053(10) 0.0003(9) C31 0.0279(16) 0.0241(12) 0.0317(12) -0.0138(10) -0.0163(11) 0.0049(9) C41 0.0202(16) 0.0399(14) 0.0222(11) -0.0135(10) 0.0003(9) -0.0073(10) C42 0.0230(15) 0.0197(11) 0.0217(11) -0.0063(9) -0.0016(9) -0.0001(9) C111 0.0143(13) 0.0200(10) 0.0180(10) -0.0036(8) -0.0009(8) 0.0010(8) C112 0.0210(15) 0.0223(11) 0.0340(13) -0.0059(10) -0.0065(10) -0.0020(9) C113 0.0196(16) 0.0303(13) 0.0366(13) -0.0027(10) -0.0124(11) -0.0004(10) C114 0.0221(15) 0.0241(12) 0.0274(12) 0.0008(9) -0.0033(10) 0.0064(9) C115 0.0235(15) 0.0201(11) 0.0271(12) -0.0041(9) -0.0008(10) 0.0002(9) C116 0.0199(14) 0.0238(11) 0.0207(11) -0.0056(9) -0.0047(9) -0.0001(9) C131 0.0178(14) 0.0156(10) 0.0186(10) -0.0042(8) -0.0064(9) -0.0020(8) C132 0.0200(14) 0.0226(11) 0.0204(11) -0.0069(9) -0.0035(9) -0.0033(9) C133 0.0318(16) 0.0227(11) 0.0239(11) -0.0029(9) -0.0049(10) -0.0097(10) C134 0.0335(17) 0.0152(11) 0.0339(13) -0.0052(9) -0.0156(11) -0.0012(9) C135 0.0189(15) 0.0239(12) 0.0399(13) -0.0168(10) -0.0094(10) 0.0036(9) C136 0.0184(14) 0.0229(11) 0.0231(11) -0.0069(9) -0.0033(9) -0.0036(9) C161 0.0252(16) 0.0309(13) 0.0262(12) 0.0050(10) -0.0062(10) 0.0011(10) C162 0.044(2) 0.0370(16) 0.083(2) -0.0249(15) -0.0276(17) 0.0044(13) C163 0.043(2) 0.060(2) 0.090(2) -0.0538(19) -0.0321(18) 0.0204(15) C164 0.0214(19) 0.087(2) 0.0379(15) -0.0324(15) -0.0111(12) 0.0137(14) C165 0.0206(16) 0.0373(14) 0.0318(13) -0.0034(11) -0.0094(11) 0.0029(10) C32A 0.063(2) 0.0276(14) 0.0529(18) -0.0134(13) 0.0186(15) -0.0159(13) C33A 0.093(5) 0.0254(18) 0.025(4) -0.002(2) -0.013(3) -0.019(2) C34A 0.083(5) 0.021(4) 0.084(8) -0.026(5) -0.045(5) 0.006(3) C35A 0.047(3) 0.057(3) 0.118(6) -0.065(4) -0.013(4) 0.015(2) C36A 0.034(3) 0.040(3) 0.076(4) -0.038(3) 0.001(3) -0.0031(18) C43A 0.0199(15) 0.0258(12) 0.0355(13) -0.0093(10) -0.0055(10) -0.0019(9) C44A 0.017(2) 0.020(3) 0.0328(16) -0.006(2) 0.0026(13) -0.001(2) C45A 0.029(3) 0.056(3) 0.0193(19) -0.013(2) 0.0060(17) -0.016(2) C46A 0.030(3) 0.050(3) 0.027(2) -0.021(2) -0.0016(17) -0.013(2) C32B 0.063(2) 0.0276(14) 0.0529(18) -0.0134(13) 0.0186(15) -0.0159(13) C33B 0.093(5) 0.0254(18) 0.025(4) -0.002(2) -0.013(3) -0.019(2) C34B 0.083(5) 0.021(4) 0.084(8) -0.026(5) -0.045(5) 0.006(3) C35B 0.047(3) 0.057(3) 0.118(6) -0.065(4) -0.013(4) 0.015(2) C36B 0.034(3) 0.040(3) 0.076(4) -0.038(3) 0.001(3) -0.0031(18) C43B 0.0199(15) 0.0258(12) 0.0355(13) -0.0093(10) -0.0055(10) -0.0019(9) C44B 0.017(2) 0.020(3) 0.0328(16) -0.006(2) 0.0026(13) -0.001(2) C45B 0.028(7) 0.091(11) 0.029(5) -0.027(6) 0.007(4) -0.015(6) C46B 0.016(6) 0.062(8) 0.035(5) -0.032(6) 0.009(4) -0.015(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cu1 N11 2.1234(17) . ? Cu1 N13 2.1273(17) . ? Cu1 P1 2.1897(6) . ? Cu1 Cl1 2.2752(5) . ? P1 C31 1.827(2) . ? P1 C21 1.830(2) . ? P1 C41 1.834(2) . ? N11 C11 1.324(3) . ? N11 N12 1.378(2) . ? N12 C13 1.383(3) . ? N12 C14 1.413(3) . ? N13 C17 1.325(3) . ? N13 C14 1.346(3) . ? N14 C17 1.323(3) . ? N14 C16 1.365(3) . ? N15 C16 1.355(3) . ? N15 C161 1.461(3) . ? N15 C165 1.464(3) . ? C11 C12 1.414(3) . ? C11 C111 1.475(3) . ? C12 C13 1.370(3) . ? C12 H12 0.9500 . ? C13 C131 1.476(3) . ? C14 C15 1.369(3) . ? C15 C16 1.405(3) . ? C15 H15 0.9500 . ? C17 H17 0.9500 . ? C21 C22 1.387(3) . ? C21 C26 1.398(3) . ? C22 C23 1.394(3) . ? C22 H22 0.9500 . ? C23 C24 1.379(3) . ? C23 H23 0.9500 . ? C24 C25 1.385(3) . ? C24 H24 0.9500 . ? C25 C26 1.385(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C36B 1.334(10) . ? C31 C32A 1.359(4) . ? C31 C36A 1.431(5) . ? C41 C42 1.374(3) . ? C41 C46A 1.413(5) . ? C41 C46B 1.466(10) . ? C42 C43A 1.388(3) . ? C42 H42 0.9500 . ? C111 C112 1.387(3) . ? C111 C116 1.397(3) . ? C112 C113 1.390(3) . ? C112 H112 0.9500 . ? C113 C114 1.380(3) . ? C113 H113 0.9500 . ? C114 C115 1.384(3) . ? C114 H114 0.9500 . ? C115 C116 1.388(3) . ? C115 H115 0.9500 . ? C116 H116 0.9500 . ? C131 C136 1.394(3) . ? C131 C132 1.395(3) . ? C132 C133 1.386(3) . ? C132 H132 0.9500 . ? C133 C134 1.381(3) . ? C133 H133 0.9500 . ? C134 C135 1.385(3) . ? C134 H134 0.9500 . ? C135 C136 1.387(3) . ? C135 H135 0.9500 . ? C136 H136 0.9500 . ? C161 C162 1.515(4) . ? C161 H16C 0.9900 . ? C161 H16D 0.9900 . ? C162 C163 1.527(4) . ? C162 H16G 0.9900 . ? C162 H16H 0.9900 . ? C163 C164 1.520(4) . ? C163 H16I 0.9900 . ? C163 H16J 0.9900 . ? C164 C165 1.507(4) . ? C164 H16E 0.9900 . ? C164 H16F 0.9900 . ? C165 H16A 0.9900 . ? C165 H16B 0.9900 . ? C32A C33A 1.389(7) . ? C32A H32A 0.9500 . ? C33A C34A 1.364(11) . ? C33A H33A 0.9500 . ? C34A C35A 1.399(10) . ? C34A H34A 0.9500 . ? C35A C36A 1.400(6) . ? C35A H35A 0.9500 . ? C36A H36A 0.9500 . ? C43A C44A 1.342(5) . ? C43A H43A 0.9500 . ? C44A C45A 1.393(7) . ? C44A H44A 0.9500 . ? C45A C46A 1.384(6) . ? C45A H45A 0.9500 . ? C46A H46A 0.9500 . ? C33B C34B 1.366(19) . ? C33B H33B 0.9500 . ? C34B C35B 1.350(19) . ? C34B H34B 0.9500 . ? C35B C36B 1.390(13) . ? C35B H35B 0.9500 . ? C36B H36B 0.9500 . ? C44B C45B 1.378(16) . ? C44B H44B 0.9500 . ? C45B C46B 1.364(13) . ? C45B H45B 0.9500 . ? C46B H46B 0.9500 . ? 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 N11 Cu1 N13 76.75(7) . . ? N11 Cu1 P1 113.79(5) . . ? N13 Cu1 P1 110.28(5) . . ? N11 Cu1 Cl1 114.85(5) . . ? N13 Cu1 Cl1 100.88(5) . . ? P1 Cu1 Cl1 126.67(2) . . ? C31 P1 C21 100.75(10) . . ? C31 P1 C41 106.69(11) . . ? C21 P1 C41 102.86(10) . . ? C31 P1 Cu1 109.89(7) . . ? C21 P1 Cu1 122.98(7) . . ? C41 P1 Cu1 112.14(7) . . ? C11 N11 N12 106.07(16) . . ? C11 N11 Cu1 135.16(13) . . ? N12 N11 Cu1 110.87(13) . . ? N11 N12 C13 110.75(17) . . ? N11 N12 C14 117.36(16) . . ? C13 N12 C14 131.89(17) . . ? C17 N13 C14 114.52(18) . . ? C17 N13 Cu1 128.33(14) . . ? C14 N13 Cu1 115.79(15) . . ? C17 N14 C16 115.7(2) . . ? C16 N15 C161 122.6(2) . . ? C16 N15 C165 121.56(19) . . ? C161 N15 C165 112.20(18) . . ? N11 C11 C12 110.42(18) . . ? N11 C11 C111 121.18(18) . . ? C12 C11 C111 128.4(2) . . ? C13 C12 C11 106.78(19) . . ? C13 C12 H12 126.6 . . ? C11 C12 H12 126.6 . . ? C12 C13 N12 105.97(18) . . ? C12 C13 C131 128.55(19) . . ? N12 C13 C131 125.3(2) . . ? N13 C14 C15 123.4(2) . . ? N13 C14 N12 113.16(18) . . ? C15 C14 N12 123.39(18) . . ? C14 C15 C16 116.87(19) . . ? C14 C15 H15 121.6 . . ? C16 C15 H15 121.6 . . ? N15 C16 N14 115.6(2) . . ? N15 C16 C15 123.9(2) . . ? N14 C16 C15 120.46(19) . . ? N14 C17 N13 128.7(2) . . ? N14 C17 H17 115.7 . . ? N13 C17 H17 115.7 . . ? C22 C21 C26 118.7(2) . . ? C22 C21 P1 119.01(16) . . ? C26 C21 P1 122.28(17) . . ? C21 C22 C23 120.4(2) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 120.1(2) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 120.2(2) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C24 C25 C26 119.7(2) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C25 C26 C21 120.9(2) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C36B C31 C32A 104.3(6) . . ? C36B C31 C36A 34.7(5) . . ? C32A C31 C36A 120.4(3) . . ? C36B C31 P1 130.4(5) . . ? C32A C31 P1 116.9(2) . . ? C36A C31 P1 122.5(2) . . ? C42 C41 C46A 115.0(3) . . ? C42 C41 C46B 119.4(4) . . ? C46A C41 C46B 34.4(5) . . ? C42 C41 P1 118.67(17) . . ? C46A C41 P1 124.6(2) . . ? C46B C41 P1 117.5(4) . . ? C41 C42 C43A 121.6(2) . . ? C41 C42 H42 119.2 . . ? C43A C42 H42 119.2 . . ? C112 C111 C116 119.12(19) . . ? C112 C111 C11 120.48(19) . . ? C116 C111 C11 120.38(19) . . ? C111 C112 C113 120.1(2) . . ? C111 C112 H112 120.0 . . ? C113 C112 H112 120.0 . . ? C114 C113 C112 120.7(2) . . ? C114 C113 H113 119.7 . . ? C112 C113 H113 119.7 . . ? C113 C114 C115 119.6(2) . . ? C113 C114 H114 120.2 . . ? C115 C114 H114 120.2 . . ? C114 C115 C116 120.2(2) . . ? C114 C115 H115 119.9 . . ? C116 C115 H115 119.9 . . ? C115 C116 C111 120.3(2) . . ? C115 C116 H116 119.9 . . ? C111 C116 H116 119.9 . . ? C136 C131 C132 119.25(19) . . ? C136 C131 C13 121.89(18) . . ? C132 C131 C13 118.7(2) . . ? C133 C132 C131 120.3(2) . . ? C133 C132 H132 119.9 . . ? C131 C132 H132 119.9 . . ? C134 C133 C132 120.2(2) . . ? C134 C133 H133 119.9 . . ? C132 C133 H133 119.9 . . ? C133 C134 C135 119.9(2) . . ? C133 C134 H134 120.0 . . ? C135 C134 H134 120.0 . . ? C134 C135 C136 120.3(2) . . ? C134 C135 H135 119.9 . . ? C136 C135 H135 119.9 . . ? C135 C136 C131 120.0(2) . . ? C135 C136 H136 120.0 . . ? C131 C136 H136 120.0 . . ? N15 C161 C162 109.3(2) . . ? N15 C161 H16C 109.8 . . ? C162 C161 H16C 109.8 . . ? N15 C161 H16D 109.8 . . ? C162 C161 H16D 109.8 . . ? H16C C161 H16D 108.3 . . ? C161 C162 C163 110.9(2) . . ? C161 C162 H16G 109.5 . . ? C163 C162 H16G 109.5 . . ? C161 C162 H16H 109.5 . . ? C163 C162 H16H 109.5 . . ? H16G C162 H16H 108.0 . . ? C164 C163 C162 111.7(2) . . ? C164 C163 H16I 109.3 . . ? C162 C163 H16I 109.3 . . ? C164 C163 H16J 109.3 . . ? C162 C163 H16J 109.3 . . ? H16I C163 H16J 107.9 . . ? C165 C164 C163 110.5(2) . . ? C165 C164 H16E 109.5 . . ? C163 C164 H16E 109.5 . . ? C165 C164 H16F 109.5 . . ? C163 C164 H16F 109.5 . . ? H16E C164 H16F 108.1 . . ? N15 C165 C164 109.3(2) . . ? N15 C165 H16A 109.8 . . ? C164 C165 H16A 109.8 . . ? N15 C165 H16B 109.8 . . ? C164 C165 H16B 109.8 . . ? H16A C165 H16B 108.3 . . ? C31 C32A C33A 120.8(5) . . ? C31 C32A H32A 119.6 . . ? C33A C32A H32A 119.6 . . ? C34A C33A C32A 118.3(9) . . ? C34A C33A H33A 120.9 . . ? C32A C33A H33A 120.9 . . ? C33A C34A C35A 122.8(9) . . ? C33A C34A H34A 118.6 . . ? C35A C34A H34A 118.6 . . ? C34A C35A C36A 118.5(7) . . ? C34A C35A H35A 120.7 . . ? C36A C35A H35A 120.7 . . ? C35A C36A C31 118.0(4) . . ? C35A C36A H36A 121.0 . . ? C31 C36A H36A 121.0 . . ? C44A C43A C42 123.1(3) . . ? C44A C43A H43A 118.5 . . ? C42 C43A H43A 118.5 . . ? C43A C44A C45A 117.0(4) . . ? C43A C44A H44A 121.5 . . ? C45A C44A H44A 121.5 . . ? C46A C45A C44A 120.7(4) . . ? C46A C45A H45A 119.6 . . ? C44A C45A H45A 119.6 . . ? C45A C46A C41 121.9(3) . . ? C45A C46A H46A 119.1 . . ? C41 C46A H46A 119.1 . . ? C34B C33B H33B 120.7 . . ? C35B C34B C33B 111(3) . . ? C35B C34B H34B 124.5 . . ? C33B C34B H34B 124.5 . . ? C34B C35B C36B 124.7(19) . . ? C34B C35B H35B 117.6 . . ? C36B C35B H35B 117.6 . . ? C31 C36B C35B 125.9(11) . . ? C31 C36B H36B 117.0 . . ? C35B C36B H36B 117.0 . . ? C45B C44B H44B 118.7 . . ? C46B C45B C44B 121.9(9) . . ? C46B C45B H45B 119.1 . . ? C44B C45B H45B 119.1 . . ? C45B C46B C41 115.2(8) . . ? C45B C46B H46B 122.4 . . ? C41 C46B H46B 122.4 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.379 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.053 _database_code_depnum_ccdc_archive 'CCDC 915217' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C42 H38 Cu I N5 P' _chemical_formula_sum 'C42 H38 Cu I N5 P' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour yellow _diffrn_ambient_temperature 150(2) _chemical_formula_weight 834.18 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' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5244(3) _cell_length_b 17.7367(7) _cell_length_c 20.6698(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.1900(10) _cell_angle_gamma 90.00 _cell_volume 3740.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8214 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 26.35 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 1.489 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5804 _exptl_absorpt_correction_T_max 0.6238 _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius X8Apex CCD area-detector' _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean 25 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 21289 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 26.02 _reflns_number_total 7302 _reflns_number_gt 5703 _reflns_threshold_expression >2\s(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT (Bruker, 2004)' _computing_structure_solution 'SHELXTL (Bruker, 2004)' _computing_structure_refinement 'SHELXTL (Bruker, 2004)' _computing_molecular_graphics 'SHELXTL (Bruker, 2004)' _computing_publication_material 'SHELXTL (Bruker, 2004)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0283P)^2^+1.4054P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7302 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0256 _refine_ls_wR_factor_ref 0.0615 _refine_ls_wR_factor_gt 0.0583 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.232888(15) 0.519277(9) 0.185742(8) 0.02654(6) Uani 1 1 d . . . Cu1 Cu 0.18098(3) 0.528881(15) 0.302257(14) 0.02000(8) Uani 1 1 d . . . P1 P 0.17468(6) 0.42562(3) 0.36028(3) 0.01982(13) Uani 1 1 d . . . N13 N 0.32198(17) 0.60805(10) 0.35104(10) 0.0203(4) Uani 1 1 d . . . N14 N 0.53678(18) 0.66111(11) 0.38093(10) 0.0237(4) Uani 1 1 d . . . N11 N 0.06545(17) 0.62402(10) 0.30523(9) 0.0178(4) Uani 1 1 d . . . N12 N 0.13513(17) 0.67847(10) 0.34703(9) 0.0168(4) Uani 1 1 d . . . N15 N 0.57273(18) 0.78612(11) 0.41077(12) 0.0323(5) Uani 1 1 d . . . C41 C 0.3207(2) 0.36694(13) 0.36667(12) 0.0235(5) Uani 1 1 d . . . C135 C 0.1790(2) 0.83906(15) 0.51974(13) 0.0310(6) Uani 1 1 d . . . H135 H 0.2251 0.8285 0.5644 0.037 Uiso 1 1 calc R . . C131 C 0.0896(2) 0.79731(13) 0.40672(12) 0.0191(5) Uani 1 1 d . . . C12 C -0.0678(2) 0.71858(13) 0.32022(11) 0.0204(5) Uani 1 1 d . . . H12 H -0.1450 0.7479 0.3158 0.025 Uiso 1 1 calc R . . C11 C -0.0581(2) 0.64848(12) 0.28947(11) 0.0189(5) Uani 1 1 d . . . C36 C -0.0800(2) 0.38635(14) 0.29745(12) 0.0276(6) Uani 1 1 d . . . H36 H -0.0898 0.4384 0.2866 0.033 Uiso 1 1 calc R . . C165 C 0.7136(2) 0.77717(14) 0.41712(13) 0.0288(6) Uani 1 1 d . . . H16A H 0.7399 0.8070 0.3821 0.035 Uiso 1 1 calc R . . H16B H 0.7335 0.7235 0.4107 0.035 Uiso 1 1 calc R . . C14 C 0.2740(2) 0.67617(12) 0.36055(11) 0.0178(5) Uani 1 1 d . . . C31 C 0.0412(2) 0.35868(13) 0.33216(12) 0.0208(5) Uani 1 1 d . . . C115 C -0.2621(2) 0.52193(14) 0.15658(14) 0.0315(6) Uani 1 1 d . . . H115 H -0.2516 0.4879 0.1228 0.038 Uiso 1 1 calc R . . C13 C 0.0543(2) 0.73634(12) 0.35740(11) 0.0191(5) Uani 1 1 d . . . C24 C 0.1817(3) 0.47578(16) 0.58051(14) 0.0435(8) Uani 1 1 d . . . H24 H 0.1845 0.4868 0.6258 0.052 Uiso 1 1 calc R . . C22 C 0.2580(3) 0.49826(15) 0.48199(14) 0.0366(7) Uani 1 1 d . . . H22 H 0.3126 0.5254 0.4598 0.044 Uiso 1 1 calc R . . C21 C 0.1741(2) 0.44233(14) 0.44764(12) 0.0261(6) Uani 1 1 d . . . C32 C 0.0531(2) 0.28155(13) 0.34624(13) 0.0270(6) Uani 1 1 d . . . H32 H 0.1358 0.2614 0.3687 0.032 Uiso 1 1 calc R . . C112 C -0.2939(2) 0.61986(16) 0.25519(14) 0.0348(7) Uani 1 1 d . . . H112 H -0.3054 0.6531 0.2893 0.042 Uiso 1 1 calc R . . C33 C -0.0545(3) 0.23408(14) 0.32780(13) 0.0316(6) Uani 1 1 d . . . H33 H -0.0454 0.1819 0.3383 0.038 Uiso 1 1 calc R . . C113 C -0.4011(2) 0.58497(17) 0.21490(15) 0.0400(7) Uani 1 1 d . . . H113 H -0.4861 0.5944 0.2212 0.048 Uiso 1 1 calc R . . C136 C 0.1565(2) 0.78187(14) 0.47237(12) 0.0251(5) Uani 1 1 d . . . H136 H 0.1868 0.7322 0.4847 0.030 Uiso 1 1 calc R . . C26 C 0.0938(2) 0.40464(14) 0.48097(13) 0.0301(6) Uani 1 1 d . . . H26 H 0.0354 0.3669 0.4584 0.036 Uiso 1 1 calc R . . C114 C -0.3857(3) 0.53648(15) 0.16542(15) 0.0347(7) Uani 1 1 d . . . H114 H -0.4602 0.5130 0.1373 0.042 Uiso 1 1 calc R . . C133 C 0.0667(2) 0.92652(13) 0.43727(13) 0.0263(6) Uani 1 1 d . . . H133 H 0.0351 0.9761 0.4254 0.032 Uiso 1 1 calc R . . C35 C -0.1868(3) 0.33834(17) 0.27863(14) 0.0369(7) Uani 1 1 d . . . H35 H -0.2692 0.3577 0.2548 0.044 Uiso 1 1 calc R . . C164 C 0.7900(2) 0.80295(15) 0.48448(14) 0.0350(6) Uani 1 1 d . . . H16C H 0.8850 0.7986 0.4872 0.042 Uiso 1 1 calc R . . H16D H 0.7695 0.7702 0.5193 0.042 Uiso 1 1 calc R . . C15 C 0.3493(2) 0.73899(13) 0.37845(11) 0.0199(5) Uani 1 1 d . . . H15 H 0.3113 0.7867 0.3828 0.024 Uiso 1 1 calc R . . C17 C 0.4529(2) 0.60604(14) 0.36162(12) 0.0253(6) Uani 1 1 d . . . H17 H 0.4894 0.5588 0.3542 0.030 Uiso 1 1 calc R . . C116 C -0.1532(2) 0.55704(13) 0.19703(12) 0.0243(5) Uani 1 1 d . . . H116 H -0.0684 0.5469 0.1908 0.029 Uiso 1 1 calc R . . C134 C 0.1346(2) 0.91124(14) 0.50204(13) 0.0299(6) Uani 1 1 d . . . H134 H 0.1508 0.9504 0.5344 0.036 Uiso 1 1 calc R . . C16 C 0.4866(2) 0.72960(13) 0.39020(12) 0.0221(5) Uani 1 1 d . . . C34 C -0.1744(3) 0.26255(16) 0.29430(13) 0.0344(7) Uani 1 1 d . . . H34 H -0.2483 0.2301 0.2820 0.041 Uiso 1 1 calc R . . C132 C 0.0443(2) 0.86998(13) 0.38958(12) 0.0216(5) Uani 1 1 d . . . H132 H -0.0021 0.8809 0.3451 0.026 Uiso 1 1 calc R . . C23 C 0.2622(3) 0.51446(17) 0.54804(15) 0.0451(8) Uani 1 1 d . . . H23 H 0.3203 0.5521 0.5711 0.054 Uiso 1 1 calc R . . C162 C 0.6101(3) 0.89283(17) 0.48871(16) 0.0457(8) Uani 1 1 d . . . H16E H 0.5831 0.8645 0.5244 0.055 Uiso 1 1 calc R . . H16F H 0.5890 0.9467 0.4930 0.055 Uiso 1 1 calc R . . C111 C -0.1677(2) 0.60680(13) 0.24636(12) 0.0202(5) Uani 1 1 d . . . C45 C 0.4603(3) 0.30301(19) 0.30775(16) 0.0531(9) Uani 1 1 d . . . H45 H 0.4816 0.2904 0.2670 0.064 Uiso 1 1 calc R . . C46 C 0.3537(3) 0.34847(15) 0.30721(14) 0.0356(7) Uani 1 1 d . . . H46 H 0.3023 0.3673 0.2660 0.043 Uiso 1 1 calc R . . C25 C 0.0979(3) 0.42155(17) 0.54714(14) 0.0414(7) Uani 1 1 d . . . H25 H 0.0423 0.3953 0.5694 0.050 Uiso 1 1 calc R . . C43 C 0.5048(3) 0.29420(19) 0.42608(17) 0.0521(9) Uani 1 1 d . . . H43 H 0.5572 0.2754 0.4670 0.063 Uiso 1 1 calc R . . C44 C 0.5358(3) 0.2760(2) 0.36706(17) 0.0601(10) Uani 1 1 d . . . H44 H 0.6093 0.2448 0.3673 0.072 Uiso 1 1 calc R . . C42 C 0.3979(2) 0.33974(16) 0.42635(14) 0.0345(7) Uani 1 1 d . . . H42 H 0.3776 0.3523 0.4674 0.041 Uiso 1 1 calc R . . C161 C 0.5355(2) 0.86386(14) 0.42147(17) 0.0431(8) Uani 1 1 d . . . H16G H 0.4403 0.8660 0.4186 0.052 Uiso 1 1 calc R . . H16H H 0.5537 0.8965 0.3860 0.052 Uiso 1 1 calc R . . C163 C 0.7570(3) 0.88400(17) 0.49691(16) 0.0447(8) Uani 1 1 d . . . H16I H 0.7861 0.9175 0.4650 0.054 Uiso 1 1 calc R . . H16J H 0.8041 0.8990 0.5427 0.054 Uiso 1 1 calc R . . 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 0.02509(9) 0.03546(10) 0.01918(10) -0.00131(7) 0.00562(8) -0.00215(7) Cu1 0.02376(15) 0.01624(14) 0.01975(17) -0.00025(11) 0.00487(14) -0.00038(11) P1 0.0236(3) 0.0175(3) 0.0186(3) 0.0005(2) 0.0057(3) 0.0001(2) N13 0.0188(9) 0.0179(10) 0.0225(12) -0.0022(8) 0.0016(9) 0.0022(8) N14 0.0193(9) 0.0210(10) 0.0297(13) -0.0072(9) 0.0036(9) 0.0026(8) N11 0.0171(9) 0.0194(10) 0.0156(11) -0.0010(8) 0.0017(9) -0.0020(8) N12 0.0162(9) 0.0170(10) 0.0152(11) -0.0032(8) -0.0001(8) 0.0002(7) N15 0.0173(10) 0.0219(11) 0.0543(16) -0.0143(10) 0.0019(11) -0.0004(8) C41 0.0226(12) 0.0213(12) 0.0262(15) 0.0047(10) 0.0051(12) 0.0012(10) C135 0.0298(13) 0.0406(16) 0.0197(15) -0.0056(12) 0.0005(12) 0.0054(12) C131 0.0146(11) 0.0240(12) 0.0189(14) -0.0037(10) 0.0044(11) 0.0010(9) C12 0.0180(11) 0.0238(12) 0.0193(14) 0.0003(10) 0.0040(11) 0.0043(9) C11 0.0185(11) 0.0212(12) 0.0169(13) 0.0005(9) 0.0042(10) -0.0008(9) C36 0.0294(13) 0.0280(14) 0.0243(15) 0.0013(11) 0.0043(12) 0.0018(11) C165 0.0190(12) 0.0264(13) 0.0420(17) -0.0063(12) 0.0091(12) -0.0016(10) C14 0.0177(11) 0.0220(12) 0.0126(12) 0.0013(9) 0.0017(10) 0.0031(9) C31 0.0247(12) 0.0220(12) 0.0171(13) -0.0003(10) 0.0076(11) -0.0016(10) C115 0.0314(14) 0.0306(14) 0.0309(16) -0.0092(12) 0.0043(13) -0.0021(11) C13 0.0198(11) 0.0207(12) 0.0179(13) 0.0013(10) 0.0069(11) 0.0033(9) C24 0.068(2) 0.0428(18) 0.0204(16) 0.0027(13) 0.0120(16) 0.0209(16) C22 0.0476(17) 0.0344(15) 0.0271(16) -0.0016(12) 0.0076(15) -0.0038(13) C21 0.0312(13) 0.0248(13) 0.0208(14) 0.0021(11) 0.0036(12) 0.0065(11) C32 0.0330(13) 0.0243(13) 0.0247(15) 0.0004(11) 0.0092(12) 0.0002(11) C112 0.0235(13) 0.0459(17) 0.0363(17) -0.0167(13) 0.0099(13) -0.0068(12) C33 0.0476(16) 0.0225(13) 0.0304(16) -0.0070(11) 0.0203(14) -0.0095(12) C113 0.0210(13) 0.0501(18) 0.050(2) -0.0145(15) 0.0103(14) -0.0065(12) C136 0.0253(12) 0.0250(13) 0.0245(15) -0.0006(11) 0.0053(12) 0.0069(10) C26 0.0378(14) 0.0293(14) 0.0246(15) 0.0036(11) 0.0106(13) 0.0062(11) C114 0.0259(13) 0.0349(15) 0.0383(18) -0.0084(13) -0.0017(13) -0.0089(11) C133 0.0279(13) 0.0204(12) 0.0313(16) -0.0022(11) 0.0086(13) 0.0028(10) C35 0.0268(13) 0.0478(18) 0.0339(17) -0.0055(13) 0.0032(13) -0.0046(12) C164 0.0238(13) 0.0393(16) 0.0392(18) -0.0024(13) 0.0027(13) -0.0047(11) C15 0.0194(11) 0.0182(12) 0.0206(13) -0.0044(10) 0.0022(11) 0.0029(9) C17 0.0218(12) 0.0228(13) 0.0296(15) -0.0061(11) 0.0030(12) 0.0044(10) C116 0.0209(12) 0.0229(13) 0.0272(15) -0.0029(11) 0.0025(12) 0.0008(10) C134 0.0322(13) 0.0309(14) 0.0270(16) -0.0118(11) 0.0078(13) -0.0002(11) C16 0.0208(12) 0.0241(12) 0.0205(14) -0.0030(10) 0.0031(11) 0.0015(10) C34 0.0345(15) 0.0421(17) 0.0298(16) -0.0120(13) 0.0140(13) -0.0163(13) C132 0.0196(11) 0.0259(13) 0.0187(14) -0.0012(10) 0.0040(11) 0.0018(10) C23 0.062(2) 0.0430(18) 0.0241(17) -0.0077(13) -0.0004(16) 0.0056(15) C162 0.0397(16) 0.0356(16) 0.064(2) -0.0240(15) 0.0167(16) -0.0041(13) C111 0.0194(11) 0.0210(12) 0.0187(13) 0.0019(10) 0.0019(11) -0.0004(9) C45 0.0539(19) 0.064(2) 0.050(2) 0.0156(17) 0.0299(18) 0.0280(17) C46 0.0365(14) 0.0392(16) 0.0317(17) 0.0071(12) 0.0092(14) 0.0156(12) C25 0.0584(18) 0.0417(17) 0.0306(17) 0.0090(14) 0.0232(16) 0.0135(15) C43 0.0329(15) 0.075(2) 0.048(2) 0.0346(18) 0.0100(16) 0.0220(15) C44 0.0448(18) 0.079(3) 0.063(2) 0.031(2) 0.0271(18) 0.0410(18) C42 0.0275(13) 0.0456(17) 0.0309(17) 0.0111(13) 0.0083(13) 0.0032(12) C161 0.0243(13) 0.0241(14) 0.075(2) -0.0133(14) 0.0009(15) 0.0028(11) C163 0.0342(15) 0.0442(18) 0.051(2) -0.0209(15) 0.0010(15) -0.0067(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cu1 2.6024(3) . ? Cu1 N11 2.0896(18) . ? Cu1 N13 2.1111(19) . ? Cu1 P1 2.1992(6) . ? P1 C31 1.822(2) . ? P1 C21 1.831(2) . ? P1 C41 1.833(2) . ? N13 C17 1.341(3) . ? N13 C14 1.343(3) . ? N14 C17 1.312(3) . ? N14 C16 1.357(3) . ? N11 C11 1.333(3) . ? N11 N12 1.381(2) . ? N12 C13 1.383(3) . ? N12 C14 1.420(3) . ? N15 C16 1.349(3) . ? N15 C165 1.465(3) . ? N15 C161 1.465(3) . ? C41 C42 1.387(3) . ? C41 C46 1.396(3) . ? C135 C134 1.381(4) . ? C135 C136 1.389(3) . ? C135 H135 0.9500 . ? C131 C132 1.390(3) . ? C131 C136 1.394(3) . ? C131 C13 1.470(3) . ? C12 C13 1.363(3) . ? C12 C11 1.411(3) . ? C12 H12 0.9500 . ? C11 C111 1.472(3) . ? C36 C35 1.388(3) . ? C36 C31 1.391(3) . ? C36 H36 0.9500 . ? C165 C164 1.498(4) . ? C165 H16A 0.9900 . ? C165 H16B 0.9900 . ? C14 C15 1.365(3) . ? C31 C32 1.398(3) . ? C115 C114 1.381(4) . ? C115 C116 1.390(3) . ? C115 H115 0.9500 . ? C24 C25 1.371(4) . ? C24 C23 1.385(4) . ? C24 H24 0.9500 . ? C22 C23 1.385(4) . ? C22 C21 1.400(4) . ? C22 H22 0.9500 . ? C21 C26 1.386(3) . ? C32 C33 1.387(3) . ? C32 H32 0.9500 . ? C112 C113 1.374(3) . ? C112 C111 1.404(3) . ? C112 H112 0.9500 . ? C33 C34 1.378(4) . ? C33 H33 0.9500 . ? C113 C114 1.376(4) . ? C113 H113 0.9500 . ? C136 H136 0.9500 . ? C26 C25 1.391(4) . ? C26 H26 0.9500 . ? C114 H114 0.9500 . ? C133 C134 1.381(4) . ? C133 C132 1.385(3) . ? C133 H133 0.9500 . ? C35 C34 1.381(4) . ? C35 H35 0.9500 . ? C164 C163 1.516(4) . ? C164 H16C 0.9900 . ? C164 H16D 0.9900 . ? C15 C16 1.415(3) . ? C15 H15 0.9500 . ? C17 H17 0.9500 . ? C116 C111 1.385(3) . ? C116 H116 0.9500 . ? C134 H134 0.9500 . ? C34 H34 0.9500 . ? C132 H132 0.9500 . ? C23 H23 0.9500 . ? C162 C161 1.509(4) . ? C162 C163 1.522(4) . ? C162 H16E 0.9900 . ? C162 H16F 0.9900 . ? C45 C44 1.373(4) . ? C45 C46 1.380(4) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C25 H25 0.9500 . ? C43 C44 1.376(4) . ? C43 C42 1.386(4) . ? C43 H43 0.9500 . ? C44 H44 0.9500 . ? C42 H42 0.9500 . ? C161 H16G 0.9900 . ? C161 H16H 0.9900 . ? C163 H16I 0.9900 . ? C163 H16J 0.9900 . ? 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 N11 Cu1 N13 78.16(7) . . ? N11 Cu1 P1 124.13(5) . . ? N13 Cu1 P1 113.90(6) . . ? N11 Cu1 I1 109.62(5) . . ? N13 Cu1 I1 101.72(5) . . ? P1 Cu1 I1 119.432(19) . . ? C31 P1 C21 103.39(11) . . ? C31 P1 C41 102.70(10) . . ? C21 P1 C41 103.06(11) . . ? C31 P1 Cu1 119.51(8) . . ? C21 P1 Cu1 114.25(8) . . ? C41 P1 Cu1 112.04(8) . . ? C17 N13 C14 114.09(19) . . ? C17 N13 Cu1 129.33(15) . . ? C14 N13 Cu1 115.02(14) . . ? C17 N14 C16 116.94(19) . . ? C11 N11 N12 105.19(17) . . ? C11 N11 Cu1 142.68(16) . . ? N12 N11 Cu1 111.08(12) . . ? N11 N12 C13 111.33(17) . . ? N11 N12 C14 117.80(17) . . ? C13 N12 C14 129.30(19) . . ? C16 N15 C165 122.37(19) . . ? C16 N15 C161 124.27(19) . . ? C165 N15 C161 113.00(19) . . ? C42 C41 C46 118.9(2) . . ? C42 C41 P1 124.03(19) . . ? C46 C41 P1 117.06(19) . . ? C134 C135 C136 120.1(2) . . ? C134 C135 H135 119.9 . . ? C136 C135 H135 119.9 . . ? C132 C131 C136 119.3(2) . . ? C132 C131 C13 119.5(2) . . ? C136 C131 C13 120.8(2) . . ? C13 C12 C11 107.15(19) . . ? C13 C12 H12 126.4 . . ? C11 C12 H12 126.4 . . ? N11 C11 C12 110.5(2) . . ? N11 C11 C111 123.9(2) . . ? C12 C11 C111 125.6(2) . . ? C35 C36 C31 120.4(2) . . ? C35 C36 H36 119.8 . . ? C31 C36 H36 119.8 . . ? N15 C165 C164 110.6(2) . . ? N15 C165 H16A 109.5 . . ? C164 C165 H16A 109.5 . . ? N15 C165 H16B 109.5 . . ? C164 C165 H16B 109.5 . . ? H16A C165 H16B 108.1 . . ? N13 C14 C15 124.1(2) . . ? N13 C14 N12 113.77(19) . . ? C15 C14 N12 122.1(2) . . ? C36 C31 C32 118.5(2) . . ? C36 C31 P1 118.20(18) . . ? C32 C31 P1 123.28(18) . . ? C114 C115 C116 120.1(2) . . ? C114 C115 H115 120.0 . . ? C116 C115 H115 120.0 . . ? C12 C13 N12 105.78(19) . . ? C12 C13 C131 127.16(19) . . ? N12 C13 C131 126.4(2) . . ? C25 C24 C23 119.9(3) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C23 C22 C21 120.7(3) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C26 C21 C22 118.4(2) . . ? C26 C21 P1 124.2(2) . . ? C22 C21 P1 117.44(19) . . ? C33 C32 C31 120.8(2) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C113 C112 C111 120.6(2) . . ? C113 C112 H112 119.7 . . ? C111 C112 H112 119.7 . . ? C34 C33 C32 120.1(2) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C112 C113 C114 120.2(2) . . ? C112 C113 H113 119.9 . . ? C114 C113 H113 119.9 . . ? C135 C136 C131 120.0(2) . . ? C135 C136 H136 120.0 . . ? C131 C136 H136 120.0 . . ? C21 C26 C25 120.6(3) . . ? C21 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C113 C114 C115 120.1(2) . . ? C113 C114 H114 120.0 . . ? C115 C114 H114 120.0 . . ? C134 C133 C132 120.3(2) . . ? C134 C133 H133 119.8 . . ? C132 C133 H133 119.8 . . ? C34 C35 C36 120.5(3) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C165 C164 C163 110.7(2) . . ? C165 C164 H16C 109.5 . . ? C163 C164 H16C 109.5 . . ? C165 C164 H16D 109.5 . . ? C163 C164 H16D 109.5 . . ? H16C C164 H16D 108.1 . . ? C14 C15 C16 116.8(2) . . ? C14 C15 H15 121.6 . . ? C16 C15 H15 121.6 . . ? N14 C17 N13 128.2(2) . . ? N14 C17 H17 115.9 . . ? N13 C17 H17 115.9 . . ? C111 C116 C115 120.3(2) . . ? C111 C116 H116 119.8 . . ? C115 C116 H116 119.8 . . ? C135 C134 C133 120.0(2) . . ? C135 C134 H134 120.0 . . ? C133 C134 H134 120.0 . . ? N15 C16 N14 117.04(19) . . ? N15 C16 C15 123.1(2) . . ? N14 C16 C15 119.9(2) . . ? C33 C34 C35 119.8(2) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C133 C132 C131 120.1(2) . . ? C133 C132 H132 119.9 . . ? C131 C132 H132 119.9 . . ? C24 C23 C22 120.0(3) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C161 C162 C163 110.6(2) . . ? C161 C162 H16E 109.5 . . ? C163 C162 H16E 109.5 . . ? C161 C162 H16F 109.5 . . ? C163 C162 H16F 109.5 . . ? H16E C162 H16F 108.1 . . ? C116 C111 C112 118.6(2) . . ? C116 C111 C11 123.7(2) . . ? C112 C111 C11 117.7(2) . . ? C44 C45 C46 120.1(3) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C45 C46 C41 120.5(3) . . ? C45 C46 H46 119.7 . . ? C41 C46 H46 119.7 . . ? C24 C25 C26 120.5(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C44 C43 C42 120.6(3) . . ? C44 C43 H43 119.7 . . ? C42 C43 H43 119.7 . . ? C45 C44 C43 120.0(3) . . ? C45 C44 H44 120.0 . . ? C43 C44 H44 120.0 . . ? C43 C42 C41 119.9(3) . . ? C43 C42 H42 120.0 . . ? C41 C42 H42 120.0 . . ? N15 C161 C162 111.2(2) . . ? N15 C161 H16G 109.4 . . ? C162 C161 H16G 109.4 . . ? N15 C161 H16H 109.4 . . ? C162 C161 H16H 109.4 . . ? H16G C161 H16H 108.0 . . ? C164 C163 C162 110.3(2) . . ? C164 C163 H16I 109.6 . . ? C162 C163 H16I 109.6 . . ? C164 C163 H16J 109.6 . . ? C162 C163 H16J 109.6 . . ? H16I C163 H16J 108.1 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.348 _refine_diff_density_min -0.365 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 915218'