# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_Cu(adtp)Cl2 #TrackingRef 'CCDC 869871.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H15 Cl2 Cu N3 O S2' _chemical_formula_weight 571.96 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' S S 0.1246 0.1234 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.241(3) _cell_length_b 10.290(3) _cell_length_c 23.602(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2487.3(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4749 _cell_measurement_theta_min 2.159 _cell_measurement_theta_max 22.2455 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1156 _exptl_absorpt_coefficient_mu 1.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7395 _exptl_absorpt_correction_T_max 0.7832 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCd' _diffrn_measurement_method '\w scan' _diffrn_reflns_number 19344 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4883 _reflns_number_gt 4100 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Bruker AXS Inc., 1998.' _computing_cell_refinement 'SAINT+ Ver. 6.22, Bruker AXS Inc., 2001.' _computing_data_reduction 'SAINT+ Ver. 6.22, Bruker AXS Inc., 2001.' _computing_structure_solution 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _computing_publication_material 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _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^)+(0.1030P)^2^+0.0000P] 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_abs_structure_details 'Flack (1983), 2104 Friedel pairs' _refine_ls_abs_structure_Flack -0.022(19) _refine_ls_number_reflns 4883 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1477 _refine_ls_wR_factor_gt 0.1383 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.000 _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 0.19644(6) 0.51479(6) 0.10180(2) 0.05004(19) Uani 1 1 d . . . Cl1 Cl 0.11187(17) 0.42591(16) 0.02434(6) 0.0770(5) Uani 1 1 d . . . Cl2 Cl 0.02904(13) 0.67553(13) 0.13375(6) 0.0575(3) Uani 1 1 d . . . S1 S 0.13085(16) 0.29819(15) 0.26217(7) 0.0747(4) Uani 1 1 d . . . S2 S 0.49970(14) 0.81921(15) 0.07570(6) 0.0616(4) Uani 1 1 d . . . N1 N 0.1377(5) 0.3779(4) 0.16070(19) 0.0597(11) Uani 1 1 d . . . N2 N 0.3134(4) 0.5566(4) 0.16689(15) 0.0439(8) Uani 1 1 d . . . N3 N 0.3217(4) 0.6476(4) 0.06640(16) 0.0515(9) Uani 1 1 d . . . C1 C 0.0474(6) 0.2830(6) 0.1620(3) 0.0701(16) Uani 1 1 d . . . H1A H 0.0001 0.2567 0.1288 0.084 Uiso 1 1 d R . . C2 C 0.0303(7) 0.2290(7) 0.2126(3) 0.086(2) Uani 1 1 d . . . H2A H -0.0302 0.1596 0.2197 0.103 Uiso 1 1 d R . . C3 C 0.1917(5) 0.3958(4) 0.2112(2) 0.0504(11) Uani 1 1 d . . . C4 C 0.2895(4) 0.4982(4) 0.21596(18) 0.0447(10) Uani 1 1 d . . . C5 C 0.3512(5) 0.5399(4) 0.26585(19) 0.0459(10) Uani 1 1 d . . . H5A H 0.3323 0.4983 0.3013 0.055 Uiso 1 1 d R . . C6 C 0.4382(4) 0.6450(4) 0.26311(19) 0.0448(10) Uani 1 1 d . . . C7 C 0.4636(4) 0.7001(5) 0.20943(18) 0.0450(10) Uani 1 1 d . . . H7A H 0.5273 0.7678 0.2050 0.054 Uiso 1 1 d R . . C8 C 0.3960(4) 0.6539(5) 0.16254(18) 0.0436(10) Uani 1 1 d . . . C9 C 0.4026(4) 0.7007(5) 0.1042(2) 0.0472(10) Uani 1 1 d . . . C10 C 0.4325(6) 0.7939(7) 0.0111(2) 0.0719(17) Uani 1 1 d . . . H10A H 0.4540 0.8421 -0.0225 0.086 Uiso 1 1 d R . . C11 C 0.3383(5) 0.6964(6) 0.0148(2) 0.0644(15) Uani 1 1 d . . . H11A H 0.2917 0.6651 -0.0177 0.077 Uiso 1 1 d R . . C12 C 0.4945(4) 0.6949(4) 0.31681(18) 0.0446(10) Uani 1 1 d . . . C13 C 0.6014(5) 0.6282(5) 0.34119(19) 0.0492(11) Uani 1 1 d . . . C14 C 0.6687(5) 0.5282(5) 0.3146(2) 0.0583(13) Uani 1 1 d . . . H14A H 0.6454 0.5037 0.2767 0.070 Uiso 1 1 d R . . C15 C 0.7676(6) 0.4604(6) 0.3415(3) 0.0708(17) Uani 1 1 d . . . H15A H 0.8124 0.3910 0.3225 0.085 Uiso 1 1 d R . . C16 C 0.8039(6) 0.4964(6) 0.3973(3) 0.0760(17) Uani 1 1 d . . . H16A H 0.8717 0.4476 0.4157 0.091 Uiso 1 1 d R . . C17 C 0.7469(6) 0.5941(7) 0.4246(3) 0.0747(17) Uani 1 1 d . . . H17A H 0.7756 0.6158 0.4622 0.090 Uiso 1 1 d R . . C18 C 0.6406(5) 0.6682(5) 0.3979(2) 0.0550(12) Uani 1 1 d . . . C19 C 0.5798(6) 0.7692(6) 0.4246(2) 0.0607(14) Uani 1 1 d . . . H19A H 0.6099 0.7951 0.4614 0.073 Uiso 1 1 d R . . C20 C 0.4740(5) 0.8349(5) 0.4004(2) 0.0560(12) Uani 1 1 d . . . C21 C 0.4033(7) 0.9410(6) 0.4286(2) 0.0719(17) Uani 1 1 d . . . H21A H 0.4345 0.9709 0.4647 0.086 Uiso 1 1 d R . . C22 C 0.3036(7) 0.9985(6) 0.4048(3) 0.082(2) Uani 1 1 d . . . H22A H 0.2609 1.0677 0.4248 0.099 Uiso 1 1 d R . . C23 C 0.2566(6) 0.9584(6) 0.3521(3) 0.0746(18) Uani 1 1 d . . . H23A H 0.1800 0.9982 0.3363 0.089 Uiso 1 1 d R . . C24 C 0.3184(5) 0.8615(5) 0.3234(2) 0.0605(13) Uani 1 1 d . . . H24A H 0.2874 0.8374 0.2865 0.073 Uiso 1 1 d R . . C25 C 0.4294(5) 0.7970(5) 0.34520(19) 0.0491(11) Uani 1 1 d . . . O4W O 0.1976(10) 0.4069(9) 0.3775(4) 0.074(2) Uiso 0.45 1 d P . . O3W O 0.1652(15) 0.5329(15) 0.3967(6) 0.072(4) Uiso 0.27 1 d P . . O2W O 0.262(3) 0.511(3) 0.4008(12) 0.060(7) Uiso 0.13 1 d P . . O1W O 0.180(3) 0.629(3) 0.4214(12) 0.075(7) Uiso 0.15 1 d P . . 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 0.0553(3) 0.0528(3) 0.0420(3) -0.0045(3) -0.0055(3) -0.0003(3) Cl1 0.0963(11) 0.0744(9) 0.0603(8) -0.0208(7) -0.0256(8) 0.0092(9) Cl2 0.0589(7) 0.0559(7) 0.0576(7) -0.0063(6) 0.0057(6) 0.0017(6) S1 0.0787(10) 0.0650(9) 0.0805(10) 0.0198(8) 0.0054(8) -0.0202(8) S2 0.0630(8) 0.0714(9) 0.0504(7) 0.0135(6) 0.0049(6) -0.0101(7) N1 0.065(3) 0.050(2) 0.065(3) -0.004(2) -0.001(2) -0.005(2) N2 0.049(2) 0.046(2) 0.0365(18) -0.0010(15) 0.0007(17) -0.0061(17) N3 0.052(2) 0.061(2) 0.041(2) 0.0019(18) -0.0005(18) 0.002(2) C1 0.067(4) 0.060(3) 0.083(4) -0.009(3) 0.002(3) -0.010(3) C2 0.079(4) 0.068(4) 0.111(6) 0.011(4) -0.004(4) -0.021(3) C3 0.056(3) 0.043(2) 0.052(3) -0.001(2) 0.005(2) 0.001(2) C4 0.049(2) 0.042(2) 0.043(2) 0.0010(19) -0.0056(18) 0.002(2) C5 0.058(3) 0.041(2) 0.039(2) 0.0075(18) 0.004(2) -0.0017(19) C6 0.045(2) 0.047(2) 0.043(2) 0.001(2) 0.0004(19) 0.0041(19) C7 0.045(2) 0.051(3) 0.039(2) 0.007(2) 0.0002(18) -0.006(2) C8 0.041(2) 0.051(3) 0.039(2) 0.0019(19) 0.0060(19) 0.003(2) C9 0.050(2) 0.051(2) 0.041(2) -0.001(2) 0.002(2) 0.004(2) C10 0.075(4) 0.104(5) 0.036(2) 0.021(3) 0.005(3) 0.000(4) C11 0.069(3) 0.088(4) 0.036(2) 0.002(3) -0.001(2) 0.003(3) C12 0.052(3) 0.044(2) 0.038(2) 0.0019(19) -0.001(2) -0.004(2) C13 0.055(3) 0.046(3) 0.047(2) 0.003(2) -0.001(2) -0.003(2) C14 0.053(3) 0.057(3) 0.065(3) 0.001(2) -0.008(2) 0.001(2) C15 0.065(4) 0.053(3) 0.095(5) 0.010(3) -0.008(3) 0.008(2) C16 0.065(3) 0.075(4) 0.088(4) 0.019(4) -0.022(3) -0.005(3) C17 0.084(4) 0.080(4) 0.061(3) 0.012(3) -0.021(3) -0.018(3) C18 0.061(3) 0.061(3) 0.042(2) 0.008(2) -0.008(2) -0.010(2) C19 0.076(4) 0.070(3) 0.035(2) -0.001(2) 0.002(2) -0.021(3) C20 0.066(3) 0.060(3) 0.042(2) -0.004(2) 0.011(2) -0.017(2) C21 0.092(5) 0.068(4) 0.056(3) -0.018(3) 0.025(3) -0.021(3) C22 0.078(4) 0.072(4) 0.097(5) -0.022(4) 0.037(4) 0.003(4) C23 0.071(4) 0.065(4) 0.088(5) -0.004(3) 0.014(3) 0.006(3) C24 0.068(3) 0.049(3) 0.064(3) 0.005(2) 0.010(3) 0.005(3) C25 0.055(3) 0.047(3) 0.046(2) 0.003(2) 0.005(2) -0.009(2) _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 N2 1.995(4) . ? Cu1 N3 2.052(4) . ? Cu1 N1 2.068(4) . ? Cu1 Cl1 2.2203(15) . ? Cu1 Cl2 2.4988(14) . ? S1 C3 1.686(5) . ? S1 C2 1.713(7) . ? S2 C10 1.694(6) . ? S2 C9 1.711(5) . ? N1 C1 1.346(7) . ? N1 C3 1.327(7) . ? N2 C8 1.314(6) . ? N2 C4 1.328(6) . ? N3 C9 1.334(6) . ? N3 C11 1.328(6) . ? C1 C2 1.328(10) . ? C1 H1A 0.9600 . ? C2 H2A 0.9599 . ? C3 C4 1.459(6) . ? C4 C5 1.404(6) . ? C5 C6 1.402(6) . ? C5 H5A 0.9599 . ? C6 C7 1.412(6) . ? C6 C12 1.484(6) . ? C7 C8 1.389(6) . ? C7 H7A 0.9600 . ? C8 C9 1.461(6) . ? C10 C11 1.394(8) . ? C10 H10A 0.9602 . ? C11 H11A 0.9599 . ? C12 C13 1.415(7) . ? C12 C25 1.414(7) . ? C13 C14 1.388(7) . ? C13 C18 1.456(7) . ? C14 C15 1.383(7) . ? C14 H14A 0.9600 . ? C15 C16 1.418(9) . ? C15 H15A 0.9600 . ? C16 C17 1.330(9) . ? C16 H16A 0.9600 . ? C17 C18 1.472(8) . ? C17 H17A 0.9603 . ? C18 C19 1.366(8) . ? C19 C20 1.398(8) . ? C19 H19A 0.9599 . ? C20 C25 1.435(7) . ? C20 C21 1.469(8) . ? C21 C22 1.307(9) . ? C21 H21A 0.9600 . ? C22 C23 1.396(9) . ? C22 H22A 0.9600 . ? C23 C24 1.361(8) . ? C23 H23A 0.9600 . ? C24 C25 1.413(7) . ? C24 H24A 0.9598 . ? O4W O2W 1.37(3) . ? O4W O3W 1.412(17) . ? O3W O2W 1.02(3) . ? O3W O1W 1.16(3) . ? O2W O1W 1.56(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 N2 Cu1 N3 78.14(15) . . ? N2 Cu1 N1 78.71(16) . . ? N3 Cu1 N1 155.36(17) . . ? N2 Cu1 Cl1 163.18(12) . . ? N3 Cu1 Cl1 100.53(12) . . ? N1 Cu1 Cl1 99.17(13) . . ? N2 Cu1 Cl2 92.11(12) . . ? N3 Cu1 Cl2 96.38(12) . . ? N1 Cu1 Cl2 92.78(13) . . ? Cl1 Cu1 Cl2 104.69(6) . . ? C3 S1 C2 89.0(3) . . ? C10 S2 C9 90.4(3) . . ? C1 N1 C3 111.5(5) . . ? C1 N1 Cu1 135.2(4) . . ? C3 N1 Cu1 112.8(3) . . ? C8 N2 C4 122.1(4) . . ? C8 N2 Cu1 119.4(3) . . ? C4 N2 Cu1 117.6(3) . . ? C9 N3 C11 112.2(4) . . ? C9 N3 Cu1 112.9(3) . . ? C11 N3 Cu1 134.9(4) . . ? C2 C1 N1 114.5(6) . . ? C2 C1 H1A 123.3 . . ? N1 C1 H1A 122.1 . . ? C1 C2 S1 111.2(5) . . ? C1 C2 H2A 123.6 . . ? S1 C2 H2A 125.3 . . ? N1 C3 C4 117.1(4) . . ? N1 C3 S1 113.8(4) . . ? C4 C3 S1 129.0(4) . . ? N2 C4 C5 120.7(4) . . ? N2 C4 C3 112.7(4) . . ? C5 C4 C3 126.5(4) . . ? C4 C5 C6 118.9(4) . . ? C4 C5 H5A 120.3 . . ? C6 C5 H5A 120.8 . . ? C5 C6 C7 117.9(4) . . ? C5 C6 C12 118.3(4) . . ? C7 C6 C12 123.8(4) . . ? C8 C7 C6 119.1(4) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.9 . . ? N2 C8 C7 121.2(4) . . ? N2 C8 C9 110.7(4) . . ? C7 C8 C9 128.0(4) . . ? N3 C9 C8 117.8(4) . . ? N3 C9 S2 113.0(3) . . ? C8 C9 S2 129.2(4) . . ? C11 C10 S2 109.6(4) . . ? C11 C10 H10A 125.6 . . ? S2 C10 H10A 124.8 . . ? N3 C11 C10 114.8(5) . . ? N3 C11 H11A 122.8 . . ? C10 C11 H11A 122.3 . . ? C13 C12 C25 122.2(4) . . ? C13 C12 C6 118.7(4) . . ? C25 C12 C6 118.6(4) . . ? C14 C13 C12 124.1(4) . . ? C14 C13 C18 119.2(5) . . ? C12 C13 C18 116.7(4) . . ? C13 C14 C15 122.0(5) . . ? C13 C14 H14A 119.5 . . ? C15 C14 H14A 118.5 . . ? C14 C15 C16 119.1(6) . . ? C14 C15 H15A 120.7 . . ? C16 C15 H15A 120.2 . . ? C17 C16 C15 122.2(6) . . ? C17 C16 H16A 119.5 . . ? C15 C16 H16A 118.3 . . ? C16 C17 C18 120.6(6) . . ? C16 C17 H17A 119.3 . . ? C18 C17 H17A 120.2 . . ? C19 C18 C17 122.2(5) . . ? C19 C18 C13 120.9(5) . . ? C17 C18 C13 116.9(5) . . ? C18 C19 C20 122.2(5) . . ? C18 C19 H19A 118.9 . . ? C20 C19 H19A 118.9 . . ? C25 C20 C19 119.0(5) . . ? C25 C20 C21 117.1(5) . . ? C19 C20 C21 123.8(5) . . ? C22 C21 C20 121.8(6) . . ? C22 C21 H21A 119.7 . . ? C20 C21 H21A 118.4 . . ? C21 C22 C23 121.2(6) . . ? C21 C22 H22A 118.7 . . ? C23 C22 H22A 120.0 . . ? C24 C23 C22 120.0(6) . . ? C24 C23 H23A 119.9 . . ? C22 C23 H23A 120.1 . . ? C23 C24 C25 122.5(6) . . ? C23 C24 H24A 119.1 . . ? C25 C24 H24A 118.3 . . ? C20 C25 C12 118.8(5) . . ? C20 C25 C24 117.3(5) . . ? C12 C25 C24 123.8(5) . . ? O2W O4W O3W 42.9(13) . . ? O2W O3W O4W 66(2) . . ? O2W O3W O1W 91(3) . . ? O4W O3W O1W 156(2) . . ? O3W O2W O4W 71(2) . . ? O3W O2W O1W 48.2(19) . . ? O4W O2W O1W 118(2) . . ? O3W O1W O2W 40.9(16) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.714 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 869871' ####################################################################### # # 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_Cu(bfdtp)Cl2 #TrackingRef 'CCDC 869872.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H11 Cl2 Cu N3 O S2' _chemical_formula_weight 495.87 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' S S 0.1246 0.1234 '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' O O 0.0106 0.0060 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9078(11) _cell_length_b 11.1470(16) _cell_length_c 11.5729(16) _cell_angle_alpha 111.368(2) _cell_angle_beta 92.003(2) _cell_angle_gamma 90.218(2) _cell_volume 949.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2675 _cell_measurement_theta_min 2.5775 _cell_measurement_theta_max 26.487 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.735 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 1.668 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7104 _exptl_absorpt_correction_T_max 0.8124 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCd' _diffrn_measurement_method '\w scan' _diffrn_reflns_number 7452 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3688 _reflns_number_gt 3068 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Bruker AXS Inc., 1998.' _computing_cell_refinement 'SAINT+ Ver. 6.22, Bruker AXS Inc., 2001.' _computing_data_reduction 'SAINT+ Ver. 6.22, Bruker AXS Inc., 2001.' _computing_structure_solution 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _computing_publication_material 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _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^)+(0.0520P)^2^+0.5017P] 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 3688 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _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 0.10255(4) 0.87005(3) 0.09657(3) 0.03458(13) Uani 1 1 d . . . Cl1 Cl 0.24104(9) 0.79428(7) 0.25000(7) 0.04170(19) Uani 1 1 d . . . Cl2 Cl 0.26513(10) 0.79188(8) -0.06710(8) 0.0496(2) Uani 1 1 d . . . S1 S 0.16488(10) 1.29447(7) 0.29172(8) 0.0412(2) Uani 1 1 d . . . S2 S -0.37344(10) 0.64789(8) 0.07587(9) 0.0467(2) Uani 1 1 d . . . N1 N 0.1910(3) 1.0572(2) 0.1594(2) 0.0367(6) Uani 1 1 d . . . N2 N -0.0865(3) 0.9643(2) 0.1977(2) 0.0328(5) Uani 1 1 d . . . N3 N -0.0878(3) 0.7328(2) 0.0432(2) 0.0335(5) Uani 1 1 d . . . O1 O -0.4521(2) 1.28720(18) 0.49055(18) 0.0383(5) Uani 1 1 d . . . C1 C 0.3312(4) 1.1175(3) 0.1387(3) 0.0426(7) Uani 1 1 d . . . H1A H 0.4145 1.0739 0.0853 0.051 Uiso 1 1 calc R . . C2 C 0.3383(4) 1.2459(3) 0.2025(3) 0.0436(8) Uani 1 1 d . . . H2A H 0.4254 1.3005 0.1986 0.052 Uiso 1 1 calc R . . C3 C 0.0922(3) 1.1393(3) 0.2390(3) 0.0329(6) Uani 1 1 d . . . C4 C -0.0677(3) 1.0892(3) 0.2668(3) 0.0316(6) Uani 1 1 d . . . C5 C -0.1896(3) 1.1554(3) 0.3468(3) 0.0346(6) Uani 1 1 d . . . H5A H -0.1730 1.2418 0.3963 0.042 Uiso 1 1 calc R . . C6 C -0.3384(3) 1.0900(3) 0.3518(3) 0.0330(6) Uani 1 1 d . . . C7 C -0.3594(4) 0.9597(3) 0.2745(3) 0.0332(6) Uani 1 1 d . . . H7A H -0.4585 0.9146 0.2747 0.040 Uiso 1 1 calc R . . C8 C -0.2304(3) 0.9002(3) 0.1986(3) 0.0315(6) Uani 1 1 d . . . C9 C -0.2243(3) 0.7673(3) 0.1088(3) 0.0330(6) Uani 1 1 d . . . C10 C -0.2443(4) 0.5463(3) -0.0322(3) 0.0475(8) Uani 1 1 d . . . H10A H -0.2706 0.4609 -0.0806 0.057 Uiso 1 1 calc R . . C11 C -0.0995(4) 0.6081(3) -0.0366(3) 0.0399(7) Uani 1 1 d . . . H11A H -0.0142 0.5687 -0.0901 0.048 Uiso 1 1 calc R . . C12 C -0.4729(4) 1.1552(3) 0.4321(3) 0.0331(6) Uani 1 1 d . . . C13 C -0.5962(4) 1.3284(3) 0.5554(3) 0.0364(7) Uani 1 1 d . . . C14 C -0.6352(4) 1.4550(3) 0.6221(3) 0.0494(8) Uani 1 1 d . . . H14A H -0.5598 1.5225 0.6316 0.059 Uiso 1 1 calc R . . C15 C -0.7916(5) 1.4759(3) 0.6737(3) 0.0548(9) Uani 1 1 d . . . H15A H -0.8236 1.5598 0.7182 0.066 Uiso 1 1 calc R . . C16 C -0.9031(4) 1.3746(3) 0.6610(3) 0.0507(9) Uani 1 1 d . . . H16A H -1.0076 1.3925 0.6975 0.061 Uiso 1 1 calc R . . C17 C -0.8621(4) 1.2482(3) 0.5954(3) 0.0402(7) Uani 1 1 d . . . H17A H -0.9366 1.1808 0.5881 0.048 Uiso 1 1 calc R . . C18 C -0.7048(4) 1.2247(3) 0.5403(3) 0.0337(6) Uani 1 1 d . . . C19 C -0.6209(3) 1.1133(3) 0.4597(3) 0.0338(6) Uani 1 1 d . . . H19A H -0.6607 1.0285 0.4319 0.041 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 Cu1 0.02615(19) 0.0339(2) 0.0408(2) 0.00951(16) 0.00837(15) -0.00011(14) Cl1 0.0369(4) 0.0405(4) 0.0475(5) 0.0160(4) 0.0003(3) -0.0038(3) Cl2 0.0398(4) 0.0580(5) 0.0449(5) 0.0101(4) 0.0163(3) 0.0007(4) S1 0.0378(4) 0.0337(4) 0.0502(5) 0.0131(4) 0.0036(3) -0.0061(3) S2 0.0330(4) 0.0347(4) 0.0647(6) 0.0083(4) 0.0097(4) -0.0066(3) N1 0.0288(12) 0.0364(13) 0.0439(15) 0.0131(12) 0.0065(11) -0.0021(10) N2 0.0250(11) 0.0304(12) 0.0407(14) 0.0096(11) 0.0071(10) -0.0016(9) N3 0.0282(12) 0.0321(13) 0.0370(13) 0.0087(11) 0.0042(10) 0.0014(10) O1 0.0368(11) 0.0305(11) 0.0411(12) 0.0046(9) 0.0107(9) -0.0017(8) C1 0.0286(15) 0.052(2) 0.0495(19) 0.0204(16) 0.0061(13) -0.0041(13) C2 0.0324(16) 0.0491(19) 0.052(2) 0.0215(16) 0.0022(14) -0.0107(14) C3 0.0286(14) 0.0319(15) 0.0379(16) 0.0122(13) 0.0044(12) -0.0012(11) C4 0.0249(13) 0.0334(15) 0.0360(16) 0.0121(13) 0.0016(11) -0.0032(11) C5 0.0318(14) 0.0303(15) 0.0384(16) 0.0082(13) 0.0036(12) -0.0009(12) C6 0.0311(14) 0.0328(15) 0.0353(16) 0.0121(13) 0.0041(12) 0.0015(12) C7 0.0295(14) 0.0322(15) 0.0385(16) 0.0133(13) 0.0061(12) -0.0033(11) C8 0.0277(14) 0.0290(14) 0.0374(16) 0.0116(12) 0.0029(12) -0.0010(11) C9 0.0258(13) 0.0331(15) 0.0402(17) 0.0132(13) 0.0036(12) -0.0005(11) C10 0.0408(17) 0.0315(16) 0.057(2) 0.0011(15) 0.0005(15) -0.0028(13) C11 0.0383(16) 0.0355(16) 0.0420(18) 0.0090(14) 0.0070(13) 0.0059(13) C12 0.0350(15) 0.0289(14) 0.0328(15) 0.0081(12) 0.0037(12) 0.0006(12) C13 0.0344(15) 0.0377(16) 0.0344(16) 0.0095(13) 0.0089(12) -0.0009(12) C14 0.051(2) 0.0345(17) 0.053(2) 0.0034(15) 0.0117(16) -0.0042(15) C15 0.063(2) 0.0369(18) 0.052(2) -0.0005(16) 0.0194(17) 0.0109(16) C16 0.0451(19) 0.050(2) 0.051(2) 0.0103(17) 0.0193(16) 0.0108(16) C17 0.0340(15) 0.0462(18) 0.0399(17) 0.0141(14) 0.0130(13) 0.0030(13) C18 0.0371(15) 0.0333(15) 0.0302(15) 0.0104(13) 0.0041(12) 0.0026(12) C19 0.0337(15) 0.0306(14) 0.0357(16) 0.0098(13) 0.0073(12) 0.0000(12) _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 N2 1.987(2) . ? Cu1 N1 2.054(2) . ? Cu1 N3 2.053(2) . ? Cu1 Cl2 2.2307(9) . ? Cu1 Cl1 2.4556(9) . ? S1 C3 1.701(3) . ? S1 C2 1.714(3) . ? S2 C9 1.702(3) . ? S2 C10 1.719(3) . ? N1 C3 1.319(4) . ? N1 C1 1.367(4) . ? N2 C4 1.334(3) . ? N2 C8 1.344(3) . ? N3 C9 1.318(4) . ? N3 C11 1.361(4) . ? O1 C13 1.372(3) . ? O1 C12 1.384(3) . ? C1 C2 1.350(4) . ? C1 H1A 0.9300 . ? C2 H2A 0.9300 . ? C3 C4 1.473(4) . ? C4 C5 1.378(4) . ? C5 C6 1.396(4) . ? C5 H5A 0.9300 . ? C6 C7 1.407(4) . ? C6 C12 1.450(4) . ? C7 C8 1.377(4) . ? C7 H7A 0.9300 . ? C8 C9 1.469(4) . ? C10 C11 1.346(4) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 C19 1.350(4) . ? C13 C14 1.382(4) . ? C13 C18 1.392(4) . ? C14 C15 1.376(5) . ? C14 H14A 0.9300 . ? C15 C16 1.391(5) . ? C15 H15A 0.9300 . ? C16 C17 1.382(4) . ? C16 H16A 0.9300 . ? C17 C18 1.399(4) . ? C17 H17A 0.9300 . ? C18 C19 1.435(4) . ? C19 H19A 0.9300 . ? 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 N2 Cu1 N1 78.01(9) . . ? N2 Cu1 N3 78.18(9) . . ? N1 Cu1 N3 152.75(9) . . ? N2 Cu1 Cl2 158.36(8) . . ? N1 Cu1 Cl2 97.76(7) . . ? N3 Cu1 Cl2 99.48(7) . . ? N2 Cu1 Cl1 98.57(7) . . ? N1 Cu1 Cl1 100.39(7) . . ? N3 Cu1 Cl1 96.09(7) . . ? Cl2 Cu1 Cl1 103.06(3) . . ? C3 S1 C2 89.55(15) . . ? C9 S2 C10 89.58(15) . . ? C3 N1 C1 111.5(3) . . ? C3 N1 Cu1 113.75(19) . . ? C1 N1 Cu1 134.7(2) . . ? C4 N2 C8 120.7(2) . . ? C4 N2 Cu1 119.88(18) . . ? C8 N2 Cu1 119.39(19) . . ? C9 N3 C11 111.6(2) . . ? C9 N3 Cu1 113.75(19) . . ? C11 N3 Cu1 134.25(19) . . ? C13 O1 C12 105.6(2) . . ? C2 C1 N1 114.2(3) . . ? C2 C1 H1A 122.9 . . ? N1 C1 H1A 122.9 . . ? C1 C2 S1 110.6(2) . . ? C1 C2 H2A 124.7 . . ? S1 C2 H2A 124.7 . . ? N1 C3 C4 117.8(3) . . ? N1 C3 S1 114.0(2) . . ? C4 C3 S1 128.1(2) . . ? N2 C4 C5 121.7(2) . . ? N2 C4 C3 109.9(2) . . ? C5 C4 C3 128.3(3) . . ? C4 C5 C6 118.6(3) . . ? C4 C5 H5A 120.7 . . ? C6 C5 H5A 120.7 . . ? C5 C6 C7 119.0(3) . . ? C5 C6 C12 121.2(3) . . ? C7 C6 C12 119.8(3) . . ? C8 C7 C6 118.7(3) . . ? C8 C7 H7A 120.6 . . ? C6 C7 H7A 120.6 . . ? N2 C8 C7 121.2(3) . . ? N2 C8 C9 110.2(2) . . ? C7 C8 C9 128.7(3) . . ? N3 C9 C8 117.8(2) . . ? N3 C9 S2 113.8(2) . . ? C8 C9 S2 128.4(2) . . ? C11 C10 S2 110.2(2) . . ? C11 C10 H10A 124.9 . . ? S2 C10 H10A 124.9 . . ? C10 C11 N3 114.8(3) . . ? C10 C11 H11A 122.6 . . ? N3 C11 H11A 122.6 . . ? C19 C12 O1 111.6(2) . . ? C19 C12 C6 132.6(3) . . ? O1 C12 C6 115.7(2) . . ? O1 C13 C14 125.8(3) . . ? O1 C13 C18 110.7(2) . . ? C14 C13 C18 123.5(3) . . ? C15 C14 C13 116.4(3) . . ? C15 C14 H14A 121.8 . . ? C13 C14 H14A 121.8 . . ? C14 C15 C16 121.7(3) . . ? C14 C15 H15A 119.1 . . ? C16 C15 H15A 119.1 . . ? C17 C16 C15 121.4(3) . . ? C17 C16 H16A 119.3 . . ? C15 C16 H16A 119.3 . . ? C16 C17 C18 117.9(3) . . ? C16 C17 H17A 121.1 . . ? C18 C17 H17A 121.1 . . ? C13 C18 C17 119.1(3) . . ? C13 C18 C19 105.4(3) . . ? C17 C18 C19 135.4(3) . . ? C12 C19 C18 106.8(3) . . ? C12 C19 H19A 126.6 . . ? C18 C19 H19A 126.6 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.523 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.073 _database_code_depnum_ccdc_archive 'CCDC 869872' ####################################################################### # # 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_Cu(pdtp)Cl2 #TrackingRef 'CCDC 869873.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H22 Cl4 Cu2 N6 S4' _chemical_formula_weight 911.70 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 18.5932(18) _cell_length_b 8.4641(8) _cell_length_c 23.526(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.327(2) _cell_angle_gamma 90.00 _cell_volume 3617.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3154 _cell_measurement_theta_min 2.5645 _cell_measurement_theta_max 23.359 _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1832 _exptl_absorpt_coefficient_mu 1.739 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7224 _exptl_absorpt_correction_T_max 0.7805 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex CCd' _diffrn_measurement_method '\w scan' _diffrn_reflns_number 15196 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7026 _reflns_number_gt 4888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART Bruker AXS Inc., 1998.' _computing_cell_refinement 'SAINT+ Ver. 6.22, Bruker AXS Inc., 2001.' _computing_data_reduction 'SAINT+ Ver. 6.22, Bruker AXS Inc., 2001.' _computing_structure_solution 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _computing_publication_material 'SHELXTL Ver. 6.12, (Sheldrick, 2000)' _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^)+(0.0694P)^2^+0.0000P] 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 7026 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1318 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 0.07437(2) 0.42812(5) 0.154687(19) 0.04300(15) Uani 1 1 d . . . Cu2 Cu 0.39120(3) 0.37080(6) -0.00392(2) 0.05267(17) Uani 1 1 d . . . S1 S 0.26224(6) 0.10399(13) 0.15138(5) 0.0574(3) Uani 1 1 d . . . S2 S -0.13190(5) 0.45139(13) 0.01826(5) 0.0527(3) Uani 1 1 d . . . S4 S 0.56997(7) 0.14146(14) -0.07465(5) 0.0601(3) Uani 1 1 d . . . S3 S 0.39565(7) 0.43708(16) 0.18451(6) 0.0683(3) Uani 1 1 d . . . Cl1 Cl 0.13951(5) 0.66450(12) 0.13062(4) 0.0536(3) Uani 1 1 d . . . Cl2 Cl 0.05581(6) 0.47717(15) 0.24454(4) 0.0605(3) Uani 1 1 d . . . Cl3 Cl 0.32550(7) 0.54580(15) -0.06379(6) 0.0750(4) Uani 1 1 d . . . Cl4 Cl 0.30660(6) 0.14720(13) -0.00409(5) 0.0605(3) Uani 1 1 d . . . N1 N 0.16675(17) 0.2894(4) 0.17799(13) 0.0470(8) Uani 1 1 d . . . N3 N -0.02776(16) 0.4814(4) 0.10749(13) 0.0419(7) Uani 1 1 d . . . N6 N 0.45725(19) 0.2910(4) -0.05735(15) 0.0538(9) Uani 1 1 d . . . N4 N 0.37160(18) 0.4507(4) 0.07437(16) 0.0543(9) Uani 1 1 d . . . C15 C 0.0677(3) -0.1332(6) -0.1735(2) 0.0754(15) Uani 1 1 d . . . H15A H 0.0672 -0.1903 -0.2073 0.090 Uiso 1 1 calc R . . C32 C 0.7529(4) -0.1047(7) 0.2557(3) 0.098(2) Uani 1 1 d . . . H32A H 0.7904 -0.1523 0.2829 0.118 Uiso 1 1 calc R . . N2 N 0.07018(16) 0.3004(3) 0.08368(12) 0.0400(7) Uani 1 1 d . . . N5 N 0.47627(17) 0.2831(4) 0.05261(14) 0.0463(8) Uani 1 1 d . . . C34 C 0.7033(3) -0.0225(7) 0.1584(2) 0.0953(19) Uani 1 1 d . . . H34A H 0.7081 -0.0163 0.1199 0.114 Uiso 1 1 calc R . . C9 C -0.0449(2) 0.4107(4) 0.05629(15) 0.0411(9) Uani 1 1 d . . . C33 C 0.7567(4) -0.0979(9) 0.1988(3) 0.122(3) Uani 1 1 d . . . H33A H 0.7962 -0.1451 0.1869 0.147 Uiso 1 1 calc R . . C8 C 0.01120(19) 0.3074(4) 0.03998(15) 0.0384(8) Uani 1 1 d . . . C2 C 0.2756(2) 0.1746(5) 0.22077(17) 0.0553(11) Uani 1 1 d . . . H2A H 0.3158 0.1493 0.2503 0.066 Uiso 1 1 calc R . . C4 C 0.1272(2) 0.2073(4) 0.07944(15) 0.0424(9) Uani 1 1 d . . . C29 C 0.6427(2) 0.0440(5) 0.17434(19) 0.0514(10) Uani 1 1 d . . . C1 C 0.2205(2) 0.2717(5) 0.22731(17) 0.0497(10) Uani 1 1 d . . . H1A H 0.2192 0.3223 0.2622 0.060 Uiso 1 1 calc R . . C26 C 0.5162(2) 0.2131(5) -0.02987(17) 0.0485(10) Uani 1 1 d . . . C21 C 0.4787(2) 0.2930(5) 0.10944(17) 0.0476(9) Uani 1 1 d . . . C5 C 0.1276(2) 0.1204(4) 0.02956(16) 0.0460(9) Uani 1 1 d . . . H5A H 0.1675 0.0560 0.0276 0.055 Uiso 1 1 calc R . . C24 C 0.5831(2) 0.1211(4) 0.07169(18) 0.0487(10) Uani 1 1 d . . . H24A H 0.6181 0.0633 0.0576 0.058 Uiso 1 1 calc R . . C20 C 0.4168(2) 0.3919(5) 0.11954(19) 0.0503(10) Uani 1 1 d . . . C7 C 0.0082(2) 0.2254(4) -0.01152(16) 0.0436(9) Uani 1 1 d . . . H7A H -0.0329 0.2335 -0.0418 0.052 Uiso 1 1 calc R . . C10 C -0.1460(2) 0.5692(5) 0.07395(18) 0.0560(11) Uani 1 1 d . . . H10A H -0.1893 0.6238 0.0743 0.067 Uiso 1 1 calc R . . C12 C 0.0680(2) 0.0409(4) -0.07193(16) 0.0486(10) Uani 1 1 d . . . C3 C 0.1818(2) 0.2064(4) 0.13459(16) 0.0435(9) Uani 1 1 d . . . C13 C 0.0060(3) 0.0376(5) -0.11735(18) 0.0611(12) Uani 1 1 d . . . H13A H -0.0360 0.0939 -0.1144 0.073 Uiso 1 1 calc R . . C23 C 0.5858(2) 0.1279(4) 0.13186(17) 0.0456(9) Uani 1 1 d . . . C14 C 0.0075(3) -0.0502(6) -0.1670(2) 0.0762(15) Uani 1 1 d . . . H14A H -0.0343 -0.0522 -0.1968 0.091 Uiso 1 1 calc R . . C11 C -0.0851(2) 0.5715(5) 0.11750(18) 0.0491(10) Uani 1 1 d . . . H11A H -0.0825 0.6295 0.1515 0.059 Uiso 1 1 calc R . . C22 C 0.5318(2) 0.2175(5) 0.15007(17) 0.0502(10) Uani 1 1 d . . . H22A H 0.5317 0.2262 0.1895 0.060 Uiso 1 1 calc R . . C6 C 0.0681(2) 0.1299(4) -0.01759(15) 0.0429(9) Uani 1 1 d . . . C25 C 0.5281(2) 0.2009(5) 0.03354(17) 0.0460(9) Uani 1 1 d . . . C17 C 0.1295(3) -0.0434(5) -0.0789(2) 0.0641(12) Uani 1 1 d . . . H17A H 0.1718 -0.0414 -0.0494 0.077 Uiso 1 1 calc R . . C19 C 0.3207(3) 0.5395(6) 0.1481(2) 0.0725(14) Uani 1 1 d . . . H19A H 0.2872 0.5917 0.1658 0.087 Uiso 1 1 calc R . . C18 C 0.3168(2) 0.5343(5) 0.0908(2) 0.0643(13) Uani 1 1 d . . . H18A H 0.2796 0.5840 0.0641 0.077 Uiso 1 1 calc R . . C16 C 0.1293(3) -0.1313(6) -0.1293(2) 0.0780(15) Uani 1 1 d . . . H16A H 0.1708 -0.1885 -0.1328 0.094 Uiso 1 1 calc R . . C28 C 0.4536(3) 0.2944(5) -0.11585(19) 0.0619(12) Uani 1 1 d . . . H28A H 0.4156 0.3439 -0.1419 0.074 Uiso 1 1 calc R . . C30 C 0.6398(3) 0.0312(6) 0.2316(2) 0.0752(14) Uani 1 1 d . . . H30A H 0.5994 0.0732 0.2437 0.090 Uiso 1 1 calc R . . C27 C 0.5097(3) 0.2198(5) -0.13292(19) 0.0658(13) Uani 1 1 d . . . H27A H 0.5148 0.2121 -0.1713 0.079 Uiso 1 1 calc R . . C31 C 0.6943(3) -0.0415(7) 0.2722(2) 0.0879(17) Uani 1 1 d . . . H31A H 0.6905 -0.0468 0.3109 0.105 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 Cu1 0.0402(3) 0.0564(3) 0.0297(3) -0.0003(2) 0.0016(2) -0.0005(2) Cu2 0.0467(3) 0.0623(3) 0.0483(3) -0.0078(2) 0.0086(2) -0.0071(2) S1 0.0534(6) 0.0681(7) 0.0453(6) 0.0008(5) -0.0014(5) 0.0154(5) S2 0.0373(5) 0.0679(7) 0.0472(6) 0.0029(5) -0.0038(5) -0.0031(5) S4 0.0666(7) 0.0666(7) 0.0547(7) -0.0117(5) 0.0299(6) -0.0117(6) S3 0.0641(7) 0.0895(9) 0.0569(8) -0.0184(6) 0.0254(6) -0.0021(7) Cl1 0.0461(5) 0.0645(6) 0.0459(6) 0.0078(5) 0.0000(5) -0.0057(5) Cl2 0.0528(6) 0.0937(8) 0.0367(6) -0.0064(5) 0.0133(5) -0.0111(6) Cl3 0.0592(7) 0.0758(8) 0.0841(9) 0.0171(6) 0.0022(6) -0.0123(6) Cl4 0.0541(6) 0.0651(7) 0.0663(7) -0.0124(5) 0.0220(5) -0.0138(5) N1 0.0491(19) 0.0549(19) 0.0333(18) -0.0005(15) 0.0005(15) 0.0042(16) N3 0.0402(17) 0.0527(18) 0.0314(17) 0.0024(14) 0.0047(14) -0.0072(15) N6 0.058(2) 0.061(2) 0.045(2) -0.0079(17) 0.0156(17) -0.0121(18) N4 0.0429(19) 0.064(2) 0.056(2) -0.0183(18) 0.0105(17) -0.0016(17) C15 0.105(4) 0.075(3) 0.048(3) -0.022(2) 0.024(3) -0.016(3) C32 0.099(5) 0.114(5) 0.086(5) 0.043(4) 0.031(4) 0.043(4) N2 0.0419(17) 0.0460(17) 0.0297(16) 0.0006(13) 0.0023(14) -0.0033(14) N5 0.0444(18) 0.0551(19) 0.0407(19) -0.0092(15) 0.0118(15) -0.0103(16) C34 0.088(4) 0.138(5) 0.068(4) 0.017(3) 0.034(3) 0.043(4) C9 0.036(2) 0.053(2) 0.031(2) 0.0076(17) 0.0008(16) -0.0085(17) C33 0.109(5) 0.179(7) 0.087(5) 0.041(5) 0.037(4) 0.088(5) C8 0.041(2) 0.0403(19) 0.032(2) 0.0015(16) 0.0033(16) -0.0089(16) C2 0.059(3) 0.061(3) 0.037(2) 0.0079(19) -0.009(2) 0.006(2) C4 0.046(2) 0.048(2) 0.032(2) 0.0026(17) 0.0050(17) 0.0017(18) C29 0.049(2) 0.054(2) 0.053(3) -0.001(2) 0.017(2) -0.011(2) C1 0.053(2) 0.058(2) 0.033(2) 0.0043(18) -0.0036(18) 0.000(2) C26 0.050(2) 0.053(2) 0.045(2) -0.0129(19) 0.017(2) -0.016(2) C21 0.046(2) 0.057(2) 0.043(2) -0.0112(19) 0.0165(19) -0.0066(19) C5 0.048(2) 0.048(2) 0.040(2) 0.0002(18) 0.0050(18) 0.0008(18) C24 0.045(2) 0.048(2) 0.057(3) -0.0092(19) 0.019(2) -0.0088(18) C20 0.045(2) 0.061(2) 0.047(2) -0.013(2) 0.015(2) -0.010(2) C7 0.045(2) 0.049(2) 0.031(2) 0.0049(17) -0.0040(17) -0.0095(18) C10 0.043(2) 0.073(3) 0.053(3) 0.004(2) 0.011(2) 0.002(2) C12 0.062(3) 0.048(2) 0.034(2) 0.0003(17) 0.0064(19) -0.013(2) C3 0.044(2) 0.049(2) 0.035(2) 0.0007(18) 0.0042(17) 0.0009(18) C13 0.072(3) 0.065(3) 0.042(3) -0.004(2) 0.003(2) -0.002(2) C23 0.044(2) 0.046(2) 0.049(2) -0.0047(18) 0.0145(19) -0.0126(18) C14 0.103(4) 0.080(3) 0.037(3) -0.007(2) -0.004(3) -0.021(3) C11 0.045(2) 0.062(3) 0.041(2) 0.0016(19) 0.0106(19) -0.003(2) C22 0.050(2) 0.064(3) 0.040(2) -0.0095(19) 0.0145(19) -0.008(2) C6 0.051(2) 0.046(2) 0.030(2) 0.0034(16) 0.0049(17) -0.0106(18) C25 0.044(2) 0.054(2) 0.043(2) -0.0123(19) 0.0172(19) -0.0138(19) C17 0.065(3) 0.074(3) 0.052(3) -0.018(2) 0.010(2) -0.008(2) C19 0.059(3) 0.081(3) 0.082(4) -0.027(3) 0.027(3) -0.002(3) C18 0.047(3) 0.071(3) 0.074(3) -0.019(3) 0.009(2) -0.001(2) C16 0.088(4) 0.086(4) 0.063(3) -0.026(3) 0.022(3) -0.006(3) C28 0.075(3) 0.067(3) 0.043(3) -0.001(2) 0.011(2) -0.014(3) C30 0.071(3) 0.100(4) 0.060(3) 0.010(3) 0.027(3) 0.022(3) C27 0.085(3) 0.072(3) 0.046(3) -0.012(2) 0.027(2) -0.023(3) C31 0.105(5) 0.100(4) 0.066(4) 0.025(3) 0.034(3) 0.026(4) _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 N2 1.977(3) . ? Cu1 N3 2.035(3) . ? Cu1 N1 2.056(3) . ? Cu1 Cl2 2.2520(11) . ? Cu1 Cl1 2.4665(11) . ? Cu2 N5 1.981(3) . ? Cu2 N6 2.050(3) . ? Cu2 N4 2.066(3) . ? Cu2 Cl3 2.2217(13) . ? Cu2 Cl4 2.4604(11) . ? S1 C3 1.701(4) . ? S1 C2 1.706(4) . ? S2 C9 1.708(4) . ? S2 C10 1.711(5) . ? S4 C27 1.708(5) . ? S4 C26 1.710(4) . ? S3 C20 1.701(4) . ? S3 C19 1.708(5) . ? N1 C3 1.317(5) . ? N1 C1 1.369(4) . ? N3 C9 1.322(5) . ? N3 C11 1.372(5) . ? N6 C26 1.324(5) . ? N6 C28 1.364(5) . ? N4 C20 1.304(5) . ? N4 C18 1.362(5) . ? C15 C14 1.357(7) . ? C15 C16 1.373(7) . ? C32 C31 1.344(8) . ? C32 C33 1.356(8) . ? N2 C4 1.341(5) . ? N2 C8 1.335(4) . ? N5 C21 1.331(5) . ? N5 C25 1.342(5) . ? C34 C29 1.381(6) . ? C34 C33 1.376(7) . ? C9 C8 1.473(5) . ? C8 C7 1.387(5) . ? C2 C1 1.347(6) . ? C4 C5 1.386(5) . ? C4 C3 1.467(5) . ? C29 C30 1.364(6) . ? C29 C23 1.473(6) . ? C26 C25 1.464(5) . ? C21 C22 1.377(5) . ? C21 C20 1.482(5) . ? C5 C6 1.392(5) . ? C24 C25 1.384(6) . ? C24 C23 1.407(5) . ? C7 C6 1.407(5) . ? C10 C11 1.355(6) . ? C12 C17 1.386(6) . ? C12 C13 1.395(6) . ? C12 C6 1.484(5) . ? C13 C14 1.389(6) . ? C23 C22 1.397(5) . ? C17 C16 1.399(6) . ? C19 C18 1.335(7) . ? C28 C27 1.352(6) . ? C30 C31 1.381(7) . ? 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 N2 Cu1 N3 78.26(12) . . ? N2 Cu1 N1 78.05(12) . . ? N3 Cu1 N1 154.30(12) . . ? N2 Cu1 Cl2 155.17(9) . . ? N3 Cu1 Cl2 99.16(9) . . ? N1 Cu1 Cl2 98.15(9) . . ? N2 Cu1 Cl1 100.50(9) . . ? N3 Cu1 Cl1 98.14(9) . . ? N1 Cu1 Cl1 95.81(9) . . ? Cl2 Cu1 Cl1 104.30(4) . . ? N5 Cu2 N6 77.95(14) . . ? N5 Cu2 N4 77.97(14) . . ? N6 Cu2 N4 153.77(14) . . ? N5 Cu2 Cl3 158.08(9) . . ? N6 Cu2 Cl3 98.71(11) . . ? N4 Cu2 Cl3 99.74(11) . . ? N5 Cu2 Cl4 97.56(9) . . ? N6 Cu2 Cl4 102.24(10) . . ? N4 Cu2 Cl4 91.08(10) . . ? Cl3 Cu2 Cl4 104.30(5) . . ? C3 S1 C2 89.1(2) . . ? C9 S2 C10 90.0(2) . . ? C27 S4 C26 89.3(2) . . ? C20 S3 C19 89.1(2) . . ? C3 N1 C1 111.2(3) . . ? C3 N1 Cu1 113.7(2) . . ? C1 N1 Cu1 134.9(3) . . ? C9 N3 C11 111.3(3) . . ? C9 N3 Cu1 114.3(3) . . ? C11 N3 Cu1 134.3(3) . . ? C26 N6 C28 111.2(4) . . ? C26 N6 Cu2 114.0(3) . . ? C28 N6 Cu2 134.8(3) . . ? C20 N4 C18 110.9(4) . . ? C20 N4 Cu2 113.3(3) . . ? C18 N4 Cu2 135.1(3) . . ? C14 C15 C16 118.9(5) . . ? C31 C32 C33 119.0(5) . . ? C4 N2 C8 120.1(3) . . ? C4 N2 Cu1 119.7(2) . . ? C8 N2 Cu1 120.3(3) . . ? C21 N5 C25 119.8(3) . . ? C21 N5 Cu2 120.1(3) . . ? C25 N5 Cu2 119.9(3) . . ? C29 C34 C33 120.7(5) . . ? N3 C9 C8 117.4(3) . . ? N3 C9 S2 113.8(3) . . ? C8 C9 S2 128.8(3) . . ? C32 C33 C34 121.3(6) . . ? N2 C8 C7 121.6(4) . . ? N2 C8 C9 109.7(3) . . ? C7 C8 C9 128.8(3) . . ? C1 C2 S1 111.3(3) . . ? N2 C4 C5 121.4(3) . . ? N2 C4 C3 110.2(3) . . ? C5 C4 C3 128.2(4) . . ? C30 C29 C34 116.3(4) . . ? C30 C29 C23 122.2(4) . . ? C34 C29 C23 121.4(4) . . ? C2 C1 N1 113.9(4) . . ? N6 C26 C25 117.5(4) . . ? N6 C26 S4 114.1(3) . . ? C25 C26 S4 128.4(3) . . ? N5 C21 C22 122.2(4) . . ? N5 C21 C20 109.6(4) . . ? C22 C21 C20 128.1(4) . . ? C4 C5 C6 119.8(4) . . ? C25 C24 C23 119.7(4) . . ? N4 C20 C21 118.1(4) . . ? N4 C20 S3 114.5(3) . . ? C21 C20 S3 127.4(3) . . ? C8 C7 C6 119.4(3) . . ? C11 C10 S2 110.3(3) . . ? C17 C12 C13 117.9(4) . . ? C17 C12 C6 120.9(4) . . ? C13 C12 C6 121.2(4) . . ? N1 C3 C4 117.5(3) . . ? N1 C3 S1 114.4(3) . . ? C4 C3 S1 128.0(3) . . ? C14 C13 C12 119.5(5) . . ? C22 C23 C24 117.2(4) . . ? C22 C23 C29 120.9(4) . . ? C24 C23 C29 122.0(4) . . ? C15 C14 C13 122.5(5) . . ? C10 C11 N3 114.6(4) . . ? C21 C22 C23 119.7(4) . . ? C5 C6 C7 117.6(3) . . ? C5 C6 C12 120.8(4) . . ? C7 C6 C12 121.6(3) . . ? N5 C25 C24 121.4(4) . . ? N5 C25 C26 109.9(4) . . ? C24 C25 C26 128.7(4) . . ? C12 C17 C16 121.3(5) . . ? C18 C19 S3 110.6(4) . . ? C19 C18 N4 114.9(5) . . ? C15 C16 C17 119.9(5) . . ? C27 C28 N6 114.5(4) . . ? C29 C30 C31 122.7(5) . . ? C28 C27 S4 111.0(3) . . ? C32 C31 C30 119.9(5) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.703 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 869873'