# Electronic Supplementary Material (ESI) for CrystEngComm # 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_p1-100K _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Cu2 I2 N4' _chemical_formula_weight 649.24 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.4648(10) _cell_length_b 18.9507(10) _cell_length_c 12.1406(7) _cell_angle_alpha 90.00 _cell_angle_beta 114.5222(10) _cell_angle_gamma 90.00 _cell_volume 3865.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 5.401 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.2941 _exptl_absorpt_correction_T_max 0.5634 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7733 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_sigmaI/netI 0.0743 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3763 _reflns_number_gt 3524 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1325P)^2^+14.3222P] 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 3763 _refine_ls_number_parameters 217 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1856 _refine_ls_wR_factor_gt 0.1832 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 0.43607(5) 0.15271(4) 0.63942(8) 0.0137(3) Uani 1 1 d . . . Cu2 Cu 0.55491(5) 0.25256(4) 0.70967(8) 0.0148(3) Uani 1 1 d . . . I1 I 0.57682(3) 0.11600(2) 0.65413(4) 0.0136(2) Uani 1 1 d . . . I2 I 0.41015(3) 0.28834(2) 0.55515(4) 0.0135(2) Uani 1 1 d . . . C1 C 0.2780(4) 0.0845(4) 0.5276(6) 0.0145(14) Uani 1 1 d . . . H1 H 0.2728 0.1050 0.5953 0.017 Uiso 1 1 calc R . . C2 C 0.2155(5) 0.0454(4) 0.4481(7) 0.0167(15) Uani 1 1 d . . . H2 H 0.1692 0.0383 0.4625 0.020 Uiso 1 1 calc R . . C3 C 0.2206(5) 0.0159(3) 0.3452(7) 0.0156(15) Uani 1 1 d . . . C4 C 0.2897(5) 0.0289(4) 0.3302(7) 0.0173(15) Uani 1 1 d . . . H4 H 0.2956 0.0112 0.2612 0.021 Uiso 1 1 calc R . . C5 C 0.3505(5) 0.0680(4) 0.4168(7) 0.0186(15) Uani 1 1 d . . . H5 H 0.3978 0.0755 0.4054 0.022 Uiso 1 1 calc R . . C6 C 0.1554(5) -0.0299(4) 0.2568(7) 0.0183(15) Uani 1 1 d . . . H6A H 0.1412 -0.0123 0.1737 0.022 Uiso 1 1 calc R . . H6B H 0.1756 -0.0787 0.2614 0.022 Uiso 1 1 calc R . . C7 C 0.0346(5) 0.0322(4) 0.2321(7) 0.0180(15) Uani 1 1 d . . . H7A H 0.0144 0.0330 0.1427 0.022 Uiso 1 1 calc R . . H7B H 0.0673 0.0750 0.2643 0.022 Uiso 1 1 calc R . . C8 C 0.0351(4) -0.0939(4) 0.2336(8) 0.0202(16) Uani 1 1 d . . . H8A H 0.0679 -0.1365 0.2677 0.024 Uiso 1 1 calc R . . H8B H 0.0159 -0.0956 0.1444 0.024 Uiso 1 1 calc R . . C9 C 0.6318(4) 0.3330(4) 0.5779(7) 0.0173(15) Uani 1 1 d . . . H9 H 0.5785 0.3439 0.5247 0.021 Uiso 1 1 calc R . . C10 C 0.6906(4) 0.3563(4) 0.5464(7) 0.0175(15) Uani 1 1 d . . . H10 H 0.6780 0.3829 0.4744 0.021 Uiso 1 1 calc R . . C11 C 0.7700(4) 0.3404(4) 0.6221(7) 0.0187(14) Uani 1 1 d U . . C12 C 0.7837(5) 0.3038(4) 0.7269(7) 0.0191(16) Uani 1 1 d . . . H12 H 0.8368 0.2930 0.7816 0.023 Uiso 1 1 calc R . . C13 C 0.7206(5) 0.2824(4) 0.7536(7) 0.0200(16) Uani 1 1 d . . . H13 H 0.7318 0.2578 0.8270 0.024 Uiso 1 1 calc R . . C14 C 0.8364(4) 0.3692(5) 0.5901(7) 0.0221(15) Uani 1 1 d U . . H14A H 0.8394 0.3402 0.5243 0.026 Uiso 1 1 calc R . . H14B H 0.8229 0.4181 0.5594 0.026 Uiso 1 1 calc R . . C15 C 0.9610(4) 0.4322(4) 0.6940(6) 0.0147(14) Uani 1 1 d . . . H15A H 0.9302 0.4751 0.6931 0.018 Uiso 1 1 calc R . . H15B H 0.9718 0.4326 0.6206 0.018 Uiso 1 1 calc R . . C16 C 0.9616(5) 0.3055(4) 0.6940(7) 0.0199(16) Uani 1 1 d . . . H16A H 0.9730 0.3053 0.6212 0.024 Uiso 1 1 calc R . . H16B H 0.9306 0.2626 0.6923 0.024 Uiso 1 1 calc R . . N1 N 0.3461(4) 0.0955(3) 0.5150(5) 0.0127(12) Uani 1 1 d . . . N2 N 0.6434(4) 0.2957(3) 0.6781(6) 0.0136(13) Uani 1 1 d . . . N3 N 0.9149(4) 0.3694(3) 0.6935(6) 0.0158(12) Uani 1 1 d . . . N4 N 0.0836(4) -0.0311(3) 0.2801(6) 0.0196(14) Uani 1 1 d . . . 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 0.0117(5) 0.0150(5) 0.0161(5) -0.0036(3) 0.0074(4) -0.0023(3) Cu2 0.0098(5) 0.0184(5) 0.0184(5) 0.0047(3) 0.0080(4) -0.0013(3) I1 0.0122(3) 0.0175(3) 0.0140(3) -0.00058(15) 0.0084(2) 0.00291(16) I2 0.0117(3) 0.0131(3) 0.0137(3) 0.00142(15) 0.0032(2) 0.00134(15) C1 0.015(4) 0.016(3) 0.012(3) -0.003(3) 0.006(3) -0.001(3) C2 0.017(4) 0.021(4) 0.016(3) -0.003(3) 0.010(3) -0.001(3) C3 0.018(4) 0.009(3) 0.019(4) 0.000(3) 0.007(3) 0.000(3) C4 0.028(4) 0.013(3) 0.018(4) 0.000(3) 0.016(3) 0.004(3) C5 0.017(4) 0.023(4) 0.022(4) -0.002(3) 0.015(3) 0.000(3) C6 0.015(4) 0.013(3) 0.021(4) -0.005(3) 0.002(3) 0.003(3) C7 0.018(4) 0.015(3) 0.017(3) -0.005(3) 0.004(3) 0.001(3) C8 0.010(4) 0.012(3) 0.031(4) -0.005(3) 0.002(3) -0.001(3) C9 0.011(3) 0.022(4) 0.014(3) 0.007(3) 0.000(3) -0.001(3) C10 0.013(4) 0.023(4) 0.016(3) 0.009(3) 0.005(3) 0.002(3) C11 0.009(3) 0.026(3) 0.018(3) 0.001(3) 0.003(3) -0.006(3) C12 0.008(4) 0.024(4) 0.024(4) 0.008(3) 0.006(3) 0.003(3) C13 0.018(4) 0.020(4) 0.020(4) 0.006(3) 0.006(3) -0.002(3) C14 0.006(3) 0.037(4) 0.020(3) 0.003(3) 0.002(3) -0.004(3) C15 0.015(4) 0.017(3) 0.014(3) 0.007(3) 0.008(3) 0.006(3) C16 0.016(4) 0.015(3) 0.026(4) 0.001(3) 0.006(4) -0.001(3) N1 0.009(3) 0.012(3) 0.016(3) 0.004(2) 0.004(2) 0.004(2) N2 0.009(3) 0.018(3) 0.016(3) 0.004(2) 0.007(3) -0.003(2) N3 0.005(3) 0.020(3) 0.022(3) 0.006(3) 0.005(3) -0.002(2) N4 0.018(3) 0.012(3) 0.030(4) -0.001(3) 0.011(3) -0.005(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 Cu1 N1 2.033(6) . ? Cu1 Cu2 2.5908(12) 2_656 ? Cu1 I1 2.6238(10) . ? Cu1 I1 2.7052(10) 2_656 ? Cu1 I2 2.7343(10) . ? Cu1 Cu1 2.7425(18) 2_656 ? Cu1 Cu2 2.7513(12) . ? Cu2 N2 2.001(6) . ? Cu2 Cu1 2.5908(12) 2_656 ? Cu2 Cu2 2.5920(17) 2_656 ? Cu2 I2 2.6384(10) . ? Cu2 I2 2.7385(10) 2_656 ? Cu2 I1 2.7463(10) . ? I1 Cu1 2.7052(10) 2_656 ? I2 Cu2 2.7385(10) 2_656 ? C1 N1 1.344(9) . ? C1 C2 1.374(10) . ? C1 H1 0.9500 . ? C2 C3 1.406(10) . ? C2 H2 0.9500 . ? C3 C4 1.385(11) . ? C3 C6 1.511(10) . ? C4 C5 1.390(11) . ? C4 H4 0.9500 . ? C5 N1 1.336(10) . ? C5 H5 0.9500 . ? C6 N4 1.465(10) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N4 1.470(10) . ? C7 C7 1.511(15) 2 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N4 1.456(9) . ? C8 C8 1.506(15) 2 ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.346(9) . ? C9 C10 1.366(10) . ? C9 H9 0.9500 . ? C10 C11 1.402(10) . ? C10 H10 0.9500 . ? C11 C12 1.378(11) . ? C11 C14 1.532(10) . ? C12 C13 1.393(11) . ? C12 H12 0.9500 . ? C13 N2 1.360(10) . ? C13 H13 0.9500 . ? C14 N3 1.472(9) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N3 1.462(9) . ? C15 C15 1.515(14) 2_756 ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N3 1.485(10) . ? C16 C16 1.502(15) 2_756 ? C16 H16A 0.9900 . ? C16 H16B 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 N1 Cu1 Cu2 135.03(17) . 2_656 ? N1 Cu1 I1 112.98(17) . . ? Cu2 Cu1 I1 111.98(4) 2_656 . ? N1 Cu1 I1 101.08(17) . 2_656 ? Cu2 Cu1 I1 62.43(3) 2_656 2_656 ? I1 Cu1 I1 109.53(3) . 2_656 ? N1 Cu1 I2 105.12(16) . . ? Cu2 Cu1 I2 61.83(3) 2_656 . ? I1 Cu1 I2 106.82(3) . . ? I1 Cu1 I2 121.29(3) 2_656 . ? N1 Cu1 Cu1 146.45(16) . 2_656 ? Cu2 Cu1 Cu1 62.03(3) 2_656 2_656 ? I1 Cu1 Cu1 60.50(3) . 2_656 ? I1 Cu1 Cu1 57.58(3) 2_656 2_656 ? I2 Cu1 Cu1 108.19(2) . 2_656 ? N1 Cu1 Cu2 153.85(17) . . ? Cu2 Cu1 Cu2 57.96(4) 2_656 . ? I1 Cu1 Cu2 61.40(3) . . ? I1 Cu1 Cu2 104.78(4) 2_656 . ? I2 Cu1 Cu2 57.50(3) . . ? Cu1 Cu1 Cu2 56.28(3) 2_656 . ? N2 Cu2 Cu1 127.99(18) . 2_656 ? N2 Cu2 Cu2 154.35(18) . 2_656 ? Cu1 Cu2 Cu2 64.12(3) 2_656 2_656 ? N2 Cu2 I2 115.21(18) . . ? Cu1 Cu2 I2 116.06(4) 2_656 . ? Cu2 Cu2 I2 63.14(4) 2_656 . ? N2 Cu2 I2 103.93(19) . 2_656 ? Cu1 Cu2 I2 61.66(3) 2_656 2_656 ? Cu2 Cu2 I2 59.26(3) 2_656 2_656 ? I2 Cu2 I2 114.11(3) . 2_656 ? N2 Cu2 I1 97.02(18) . . ? Cu1 Cu2 I1 60.83(3) 2_656 . ? Cu2 Cu2 I1 108.11(2) 2_656 . ? I2 Cu2 I1 106.06(3) . . ? I2 Cu2 I1 119.63(3) 2_656 . ? N2 Cu2 Cu1 146.20(19) . . ? Cu1 Cu2 Cu1 61.69(4) 2_656 . ? Cu2 Cu2 Cu1 57.92(3) 2_656 . ? I2 Cu2 Cu1 60.93(3) . . ? I2 Cu2 Cu1 107.82(4) 2_656 . ? I1 Cu2 Cu1 57.01(3) . . ? Cu1 I1 Cu1 61.92(3) . 2_656 ? Cu1 I1 Cu2 61.59(3) . . ? Cu1 I1 Cu2 56.75(3) 2_656 . ? Cu2 I2 Cu1 61.58(3) . . ? Cu2 I2 Cu2 57.60(3) . 2_656 ? Cu1 I2 Cu2 56.51(3) . 2_656 ? N1 C1 C2 123.8(6) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C1 C2 C3 119.5(7) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 116.8(7) . . ? C4 C3 C6 121.0(7) . . ? C2 C3 C6 122.1(7) . . ? C3 C4 C5 119.6(6) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 123.6(7) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? N4 C6 C3 112.9(6) . . ? N4 C6 H6A 109.0 . . ? C3 C6 H6A 109.0 . . ? N4 C6 H6B 109.0 . . ? C3 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? N4 C7 C7 109.9(5) . 2 ? N4 C7 H7A 109.7 . . ? C7 C7 H7A 109.7 2 . ? N4 C7 H7B 109.7 . . ? C7 C7 H7B 109.7 2 . ? H7A C7 H7B 108.2 . . ? N4 C8 C8 110.9(6) . 2 ? N4 C8 H8A 109.5 . . ? C8 C8 H8A 109.5 2 . ? N4 C8 H8B 109.5 . . ? C8 C8 H8B 109.5 2 . ? H8A C8 H8B 108.1 . . ? N2 C9 C10 125.2(7) . . ? N2 C9 H9 117.4 . . ? C10 C9 H9 117.4 . . ? C9 C10 C11 118.9(7) . . ? C9 C10 H10 120.6 . . ? C11 C10 H10 120.6 . . ? C12 C11 C10 117.1(7) . . ? C12 C11 C14 123.6(7) . . ? C10 C11 C14 119.1(7) . . ? C11 C12 C13 120.7(7) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? N2 C13 C12 122.3(7) . . ? N2 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? N3 C14 C11 113.1(6) . . ? N3 C14 H14A 109.0 . . ? C11 C14 H14A 109.0 . . ? N3 C14 H14B 109.0 . . ? C11 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? N3 C15 C15 109.8(5) . 2_756 ? N3 C15 H15A 109.7 . . ? C15 C15 H15A 109.7 2_756 . ? N3 C15 H15B 109.7 . . ? C15 C15 H15B 109.7 2_756 . ? H15A C15 H15B 108.2 . . ? N3 C16 C16 109.4(6) . 2_756 ? N3 C16 H16A 109.8 . . ? C16 C16 H16A 109.8 2_756 . ? N3 C16 H16B 109.8 . . ? C16 C16 H16B 109.8 2_756 . ? H16A C16 H16B 108.2 . . ? C5 N1 C1 116.6(6) . . ? C5 N1 Cu1 122.5(5) . . ? C1 N1 Cu1 120.9(5) . . ? C9 N2 C13 115.8(6) . . ? C9 N2 Cu2 123.5(5) . . ? C13 N2 Cu2 120.5(5) . . ? C15 N3 C14 111.8(6) . . ? C15 N3 C16 109.1(6) . . ? C14 N3 C16 111.6(6) . . ? C8 N4 C6 113.5(6) . . ? C8 N4 C7 109.5(6) . . ? C6 N4 C7 111.6(6) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.793 _refine_diff_density_min -1.880 _refine_diff_density_rms 0.398 _database_code_depnum_ccdc_archive 'CCDC 959782' ####################################################################### # # 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_p1-160K _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Cu2 I2 N4' _chemical_formula_weight 649.24 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.4469(10) _cell_length_b 18.9875(11) _cell_length_c 12.1745(7) _cell_angle_alpha 90.00 _cell_angle_beta 114.5462(10) _cell_angle_gamma 90.00 _cell_volume 3878.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 5.382 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.2951 _exptl_absorpt_correction_T_max 0.5644 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7757 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0717 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3763 _reflns_number_gt 3440 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1286P)^2^+4.4561P] 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 3763 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1777 _refine_ls_wR_factor_gt 0.1711 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.43587(5) 0.15240(4) 0.63951(8) 0.0215(3) Uani 1 1 d . . . Cu2 Cu 0.55496(5) 0.25243(4) 0.70976(8) 0.0231(3) Uani 1 1 d . . . I1 I 0.57682(3) 0.11604(2) 0.65436(4) 0.0205(2) Uani 1 1 d . . . I2 I 0.41005(3) 0.28790(2) 0.55560(4) 0.0208(2) Uani 1 1 d . . . C1 C 0.2779(5) 0.0840(4) 0.5274(6) 0.0231(15) Uani 1 1 d . . . H1 H 0.2726 0.1048 0.5948 0.028 Uiso 1 1 calc R . . C2 C 0.2152(5) 0.0444(4) 0.4492(6) 0.0243(15) Uani 1 1 d . . . H2 H 0.1697 0.0364 0.4653 0.029 Uiso 1 1 calc R . . C3 C 0.2192(4) 0.0161(3) 0.3461(6) 0.0178(14) Uani 1 1 d . . . C4 C 0.2886(5) 0.0285(4) 0.3307(7) 0.0269(16) Uani 1 1 d . . . H4 H 0.2942 0.0103 0.2618 0.032 Uiso 1 1 calc R . . C5 C 0.3507(5) 0.0679(4) 0.4170(7) 0.0246(15) Uani 1 1 d . . . H5 H 0.3979 0.0755 0.4053 0.030 Uiso 1 1 calc R . . C6 C 0.1545(5) -0.0301(4) 0.2581(7) 0.0269(16) Uani 1 1 d . . . H6A H 0.1409 -0.0131 0.1751 0.032 Uiso 1 1 calc R . . H6B H 0.1750 -0.0788 0.2640 0.032 Uiso 1 1 calc R . . C7 C 0.0349(4) 0.0323(3) 0.2333(6) 0.0232(15) Uani 1 1 d . . . H7A H 0.0155 0.0341 0.1443 0.028 Uiso 1 1 calc R . . H7B H 0.0681 0.0745 0.2676 0.028 Uiso 1 1 calc R . . C8 C 0.0362(4) -0.0939(4) 0.2337(7) 0.0282(17) Uani 1 1 d . . . H8A H 0.0695 -0.1359 0.2690 0.034 Uiso 1 1 calc R . . H8B H 0.0176 -0.0960 0.1449 0.034 Uiso 1 1 calc R . . C9 C 0.6304(5) 0.3328(4) 0.5782(7) 0.0270(16) Uani 1 1 d . . . H9 H 0.5769 0.3444 0.5266 0.032 Uiso 1 1 calc R . . C10 C 0.6912(5) 0.3552(4) 0.5475(7) 0.0274(17) Uani 1 1 d . . . H10 H 0.6787 0.3803 0.4744 0.033 Uiso 1 1 calc R . . C11 C 0.7689(4) 0.3414(4) 0.6219(7) 0.0233(15) Uani 1 1 d . . . C12 C 0.7853(5) 0.3038(4) 0.7278(7) 0.0268(16) Uani 1 1 d . . . H12 H 0.8385 0.2931 0.7821 0.032 Uiso 1 1 calc R . . C13 C 0.7204(4) 0.2820(4) 0.7516(7) 0.0266(17) Uani 1 1 d . . . H13 H 0.7308 0.2564 0.8237 0.032 Uiso 1 1 calc R . . C14 C 0.8363(5) 0.3687(5) 0.5898(7) 0.036(2) Uani 1 1 d . . . H14A H 0.8387 0.3393 0.5243 0.043 Uiso 1 1 calc R . . H14B H 0.8237 0.4175 0.5590 0.043 Uiso 1 1 calc R . . C15 C 0.9608(4) 0.4313(3) 0.6945(6) 0.0218(15) Uani 1 1 d . . . H15A H 0.9299 0.4739 0.6947 0.026 Uiso 1 1 calc R . . H15B H 0.9712 0.4326 0.6210 0.026 Uiso 1 1 calc R . . C16 C 0.9616(5) 0.3051(4) 0.6942(7) 0.0304(18) Uani 1 1 d . . . H16A H 0.9730 0.3048 0.6216 0.036 Uiso 1 1 calc R . . H16B H 0.9308 0.2621 0.6926 0.036 Uiso 1 1 calc R . . N1 N 0.3457(3) 0.0952(3) 0.5149(5) 0.0169(11) Uani 1 1 d . . . N2 N 0.6450(4) 0.2955(3) 0.6777(6) 0.0224(13) Uani 1 1 d . . . N3 N 0.9144(4) 0.3680(3) 0.6926(5) 0.0237(13) Uani 1 1 d . . . N4 N 0.0829(4) -0.0311(3) 0.2794(6) 0.0222(13) Uani 1 1 d . . . 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 0.0186(5) 0.0257(5) 0.0194(5) -0.0064(3) 0.0071(4) -0.0044(3) Cu2 0.0165(5) 0.0300(5) 0.0236(5) 0.0076(3) 0.0090(4) -0.0022(3) I1 0.0192(3) 0.0275(3) 0.0171(3) -0.00074(15) 0.0097(2) 0.00450(16) I2 0.0189(3) 0.0215(3) 0.0164(3) 0.00198(15) 0.0019(2) 0.00208(16) C1 0.027(4) 0.028(3) 0.012(3) -0.003(3) 0.005(3) -0.001(3) C2 0.018(4) 0.033(4) 0.019(3) -0.004(3) 0.005(3) -0.004(3) C3 0.011(3) 0.016(3) 0.017(3) -0.001(2) -0.003(3) 0.001(2) C4 0.036(5) 0.028(3) 0.020(3) -0.006(3) 0.014(3) 0.004(3) C5 0.022(4) 0.029(3) 0.025(3) -0.005(3) 0.012(3) -0.007(3) C6 0.023(4) 0.028(3) 0.023(4) -0.008(3) 0.002(3) 0.002(3) C7 0.023(4) 0.015(3) 0.023(3) -0.004(2) 0.002(3) -0.004(3) C8 0.024(4) 0.020(3) 0.031(4) -0.007(3) 0.001(3) 0.000(3) C9 0.019(4) 0.038(4) 0.024(4) 0.010(3) 0.008(3) -0.002(3) C10 0.021(4) 0.039(4) 0.019(3) 0.012(3) 0.004(3) -0.004(3) C11 0.016(4) 0.030(4) 0.024(3) -0.002(3) 0.008(3) -0.005(3) C12 0.016(4) 0.040(4) 0.023(4) 0.010(3) 0.007(3) 0.002(3) C13 0.014(4) 0.038(4) 0.026(4) 0.015(3) 0.005(3) -0.003(3) C14 0.015(4) 0.063(5) 0.028(4) 0.017(4) 0.008(3) -0.007(4) C15 0.025(4) 0.021(3) 0.022(3) 0.008(3) 0.012(3) 0.006(3) C16 0.032(5) 0.021(3) 0.035(4) 0.004(3) 0.010(4) -0.003(3) N1 0.011(3) 0.020(3) 0.021(3) -0.001(2) 0.007(2) -0.005(2) N2 0.018(3) 0.027(3) 0.022(3) 0.004(2) 0.008(3) -0.003(2) N3 0.010(3) 0.035(3) 0.020(3) 0.007(3) 0.000(2) -0.005(3) N4 0.013(3) 0.019(3) 0.028(3) -0.005(2) 0.002(2) -0.002(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 N1 2.036(6) . ? Cu1 Cu2 2.5972(11) 2_656 ? Cu1 I1 2.6227(10) . ? Cu1 I1 2.7050(9) 2_656 ? Cu1 I2 2.7360(10) . ? Cu1 Cu1 2.7471(17) 2_656 ? Cu1 Cu2 2.7575(12) . ? Cu2 N2 2.030(6) . ? Cu2 Cu2 2.5925(18) 2_656 ? Cu2 Cu1 2.5972(11) 2_656 ? Cu2 I2 2.6368(10) . ? Cu2 I2 2.7383(10) 2_656 ? Cu2 I1 2.7477(10) . ? I1 Cu1 2.7050(9) 2_656 ? I2 Cu2 2.7383(10) 2_656 ? C1 N1 1.340(9) . ? C1 C2 1.376(10) . ? C1 H1 0.9500 . ? C2 C3 1.396(10) . ? C2 H2 0.9500 . ? C3 C4 1.389(10) . ? C3 C6 1.510(9) . ? C4 C5 1.406(10) . ? C4 H4 0.9500 . ? C5 N1 1.338(9) . ? C5 H5 0.9500 . ? C6 N4 1.448(10) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N4 1.461(9) . ? C7 C7 1.503(15) 2 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N4 1.439(9) . ? C8 C8 1.542(16) 2 ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.331(9) . ? C9 C10 1.387(10) . ? C9 H9 0.9500 . ? C10 C11 1.365(11) . ? C10 H10 0.9500 . ? C11 C12 1.394(10) . ? C11 C14 1.539(10) . ? C12 C13 1.406(10) . ? C12 H12 0.9500 . ? C13 N2 1.330(10) . ? C13 H13 0.9500 . ? C14 N3 1.464(10) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N3 1.471(9) . ? C15 C15 1.515(14) 2_756 ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N3 1.473(10) . ? C16 C16 1.502(16) 2_756 ? C16 H16A 0.9900 . ? C16 H16B 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 N1 Cu1 Cu2 135.17(17) . 2_656 ? N1 Cu1 I1 112.98(16) . . ? Cu2 Cu1 I1 111.84(4) 2_656 . ? N1 Cu1 I1 101.33(16) . 2_656 ? Cu2 Cu1 I1 62.39(3) 2_656 2_656 ? I1 Cu1 I1 109.53(3) . 2_656 ? N1 Cu1 I2 105.15(16) . . ? Cu2 Cu1 I2 61.72(3) 2_656 . ? I1 Cu1 I2 106.68(3) . . ? I1 Cu1 I2 121.17(3) 2_656 . ? N1 Cu1 Cu1 146.50(16) . 2_656 ? Cu2 Cu1 Cu1 62.05(3) 2_656 2_656 ? I1 Cu1 Cu1 60.44(3) . 2_656 ? I1 Cu1 Cu1 57.50(3) 2_656 2_656 ? I2 Cu1 Cu1 108.13(2) . 2_656 ? N1 Cu1 Cu2 153.74(16) . . ? Cu2 Cu1 Cu2 57.82(4) 2_656 . ? I1 Cu1 Cu2 61.36(3) . . ? I1 Cu1 Cu2 104.65(3) 2_656 . ? I2 Cu1 Cu2 57.37(3) . . ? Cu1 Cu1 Cu2 56.31(3) 2_656 . ? N2 Cu2 Cu2 154.65(17) . 2_656 ? N2 Cu2 Cu1 127.75(18) . 2_656 ? Cu2 Cu2 Cu1 64.19(3) 2_656 2_656 ? N2 Cu2 I2 115.40(18) . . ? Cu2 Cu2 I2 63.15(4) 2_656 . ? Cu1 Cu2 I2 116.03(4) 2_656 . ? N2 Cu2 I2 104.15(18) . 2_656 ? Cu2 Cu2 I2 59.22(3) 2_656 2_656 ? Cu1 Cu2 I2 61.63(3) 2_656 2_656 ? I2 Cu2 I2 114.19(3) . 2_656 ? N2 Cu2 I1 96.73(17) . . ? Cu2 Cu2 I1 108.08(2) 2_656 . ? Cu1 Cu2 I1 60.73(3) 2_656 . ? I2 Cu2 I1 105.94(3) . . ? I2 Cu2 I1 119.53(3) 2_656 . ? N2 Cu2 Cu1 145.91(18) . . ? Cu2 Cu2 Cu1 57.99(3) 2_656 . ? Cu1 Cu2 Cu1 61.64(4) 2_656 . ? I2 Cu2 Cu1 60.91(3) . . ? I2 Cu2 Cu1 107.77(3) 2_656 . ? I1 Cu2 Cu1 56.90(3) . . ? Cu1 I1 Cu1 62.06(3) . 2_656 ? Cu1 I1 Cu2 61.74(3) . . ? Cu1 I1 Cu2 56.88(3) 2_656 . ? Cu2 I2 Cu1 61.73(3) . . ? Cu2 I2 Cu2 57.64(3) . 2_656 ? Cu1 I2 Cu2 56.65(3) . 2_656 ? N1 C1 C2 124.4(6) . . ? N1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C1 C2 C3 119.3(7) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 116.9(6) . . ? C4 C3 C6 120.3(6) . . ? C2 C3 C6 122.6(7) . . ? C3 C4 C5 120.0(6) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? N1 C5 C4 122.5(7) . . ? N1 C5 H5 118.8 . . ? C4 C5 H5 118.8 . . ? N4 C6 C3 113.2(6) . . ? N4 C6 H6A 108.9 . . ? C3 C6 H6A 108.9 . . ? N4 C6 H6B 108.9 . . ? C3 C6 H6B 108.9 . . ? H6A C6 H6B 107.8 . . ? N4 C7 C7 110.3(5) . 2 ? N4 C7 H7A 109.6 . . ? C7 C7 H7A 109.6 2 . ? N4 C7 H7B 109.6 . . ? C7 C7 H7B 109.6 2 . ? H7A C7 H7B 108.1 . . ? N4 C8 C8 110.1(5) . 2 ? N4 C8 H8A 109.6 . . ? C8 C8 H8A 109.6 2 . ? N4 C8 H8B 109.6 . . ? C8 C8 H8B 109.6 2 . ? H8A C8 H8B 108.2 . . ? N2 C9 C10 121.8(7) . . ? N2 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C11 C10 C9 120.4(7) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C10 C11 C12 118.5(7) . . ? C10 C11 C14 120.2(7) . . ? C12 C11 C14 121.3(7) . . ? C11 C12 C13 117.7(7) . . ? C11 C12 H12 121.1 . . ? C13 C12 H12 121.1 . . ? N2 C13 C12 123.0(7) . . ? N2 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? N3 C14 C11 113.0(6) . . ? N3 C14 H14A 109.0 . . ? C11 C14 H14A 109.0 . . ? N3 C14 H14B 109.0 . . ? C11 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? N3 C15 C15 110.4(5) . 2_756 ? N3 C15 H15A 109.6 . . ? C15 C15 H15A 109.6 2_756 . ? N3 C15 H15B 109.6 . . ? C15 C15 H15B 109.6 2_756 . ? H15A C15 H15B 108.1 . . ? N3 C16 C16 110.1(6) . 2_756 ? N3 C16 H16A 109.6 . . ? C16 C16 H16A 109.6 2_756 . ? N3 C16 H16B 109.6 . . ? C16 C16 H16B 109.6 2_756 . ? H16A C16 H16B 108.2 . . ? C5 N1 C1 116.9(6) . . ? C5 N1 Cu1 122.2(5) . . ? C1 N1 Cu1 120.9(4) . . ? C13 N2 C9 118.5(7) . . ? C13 N2 Cu2 120.1(5) . . ? C9 N2 Cu2 121.2(5) . . ? C14 N3 C15 111.4(6) . . ? C14 N3 C16 112.7(7) . . ? C15 N3 C16 109.0(6) . . ? C8 N4 C6 112.7(6) . . ? C8 N4 C7 111.4(6) . . ? C6 N4 C7 111.8(6) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.325 _refine_diff_density_min -1.791 _refine_diff_density_rms 0.342 _database_code_depnum_ccdc_archive 'CCDC 959783' ####################################################################### # # 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_p1-200K _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Cu2 I2 N4' _chemical_formula_weight 649.24 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.4558(11) _cell_length_b 19.0332(11) _cell_length_c 12.2097(8) _cell_angle_alpha 90.00 _cell_angle_beta 114.5550(10) _cell_angle_gamma 90.00 _cell_volume 3901.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 5.351 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.2966 _exptl_absorpt_correction_T_max 0.5660 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8096 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0721 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3806 _reflns_number_gt 3457 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0839P)^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 3806 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1383 _refine_ls_wR_factor_gt 0.1356 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 0.43564(4) 0.15224(4) 0.63962(6) 0.0254(2) Uani 1 1 d . . . Cu2 Cu 0.55492(4) 0.25235(4) 0.70962(7) 0.0274(2) Uani 1 1 d . . . I1 I 0.57676(2) 0.116030(19) 0.65435(3) 0.02418(16) Uani 1 1 d . . . I2 I 0.40997(2) 0.287688(19) 0.55591(3) 0.02439(16) Uani 1 1 d . . . C1 C 0.2780(3) 0.0833(3) 0.5286(5) 0.0256(12) Uani 1 1 d . . . H1 H 0.2735 0.1025 0.5973 0.031 Uiso 1 1 calc R . . C2 C 0.2153(4) 0.0449(3) 0.4492(5) 0.0276(13) Uani 1 1 d . . . H2 H 0.1687 0.0383 0.4629 0.033 Uiso 1 1 calc R . . C3 C 0.2207(3) 0.0158(3) 0.3478(5) 0.0217(11) Uani 1 1 d . . . C4 C 0.2887(4) 0.0285(3) 0.3323(5) 0.0283(13) Uani 1 1 d . . . H4 H 0.2939 0.0108 0.2632 0.034 Uiso 1 1 calc R . . C5 C 0.3501(4) 0.0673(3) 0.4171(5) 0.0300(13) Uani 1 1 d . . . H5 H 0.3974 0.0743 0.4054 0.036 Uiso 1 1 calc R . . C6 C 0.1560(4) -0.0300(3) 0.2597(6) 0.0299(13) Uani 1 1 d . . . H6A H 0.1425 -0.0127 0.1770 0.036 Uiso 1 1 calc R . . H6B H 0.1765 -0.0785 0.2650 0.036 Uiso 1 1 calc R . . C7 C 0.0342(3) 0.0319(3) 0.2332(5) 0.0272(13) Uani 1 1 d . . . H7A H 0.0144 0.0331 0.1444 0.033 Uiso 1 1 calc R . . H7B H 0.0669 0.0745 0.2660 0.033 Uiso 1 1 calc R . . C8 C 0.0349(4) -0.0927(3) 0.2332(6) 0.0331(14) Uani 1 1 d . . . H8A H 0.0672 -0.1355 0.2655 0.040 Uiso 1 1 calc R . . H8B H 0.0153 -0.0934 0.1444 0.040 Uiso 1 1 calc R . . C9 C 0.6308(4) 0.3322(3) 0.5772(6) 0.0307(13) Uani 1 1 d . . . H9 H 0.5774 0.3435 0.5249 0.037 Uiso 1 1 calc R . . C10 C 0.6910(4) 0.3541(4) 0.5467(6) 0.0339(15) Uani 1 1 d . . . H10 H 0.6786 0.3790 0.4737 0.041 Uiso 1 1 calc R . . C11 C 0.7702(4) 0.3400(3) 0.6225(5) 0.0278(13) Uani 1 1 d . . . C12 C 0.7842(4) 0.3037(3) 0.7282(6) 0.0296(13) Uani 1 1 d . . . H12 H 0.8372 0.2933 0.7838 0.036 Uiso 1 1 calc R . . C13 C 0.7200(4) 0.2828(3) 0.7516(6) 0.0316(14) Uani 1 1 d . . . H13 H 0.7305 0.2580 0.8242 0.038 Uiso 1 1 calc R . . C14 C 0.8367(4) 0.3678(4) 0.5910(6) 0.0395(17) Uani 1 1 d . . . H14A H 0.8393 0.3387 0.5256 0.047 Uiso 1 1 calc R . . H14B H 0.8235 0.4164 0.5602 0.047 Uiso 1 1 calc R . . C15 C 0.9604(4) 0.4308(3) 0.6946(5) 0.0267(13) Uani 1 1 d . . . H15A H 0.9294 0.4731 0.6955 0.032 Uiso 1 1 calc R . . H15B H 0.9704 0.4324 0.6210 0.032 Uiso 1 1 calc R . . C16 C 0.9615(4) 0.3052(3) 0.6945(6) 0.0333(14) Uani 1 1 d . . . H16A H 0.9726 0.3047 0.6219 0.040 Uiso 1 1 calc R . . H16B H 0.9306 0.2625 0.6934 0.040 Uiso 1 1 calc R . . N1 N 0.3456(3) 0.0954(2) 0.5149(4) 0.0205(9) Uani 1 1 d . . . N2 N 0.6443(3) 0.2955(3) 0.6776(5) 0.0254(11) Uani 1 1 d . . . N3 N 0.9147(3) 0.3678(3) 0.6927(5) 0.0264(10) Uani 1 1 d . . . N4 N 0.0841(3) -0.0313(2) 0.2806(5) 0.0265(11) Uani 1 1 d . . . 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 0.0198(4) 0.0317(4) 0.0254(4) -0.0076(3) 0.0100(3) -0.0046(3) Cu2 0.0170(4) 0.0371(4) 0.0303(4) 0.0091(3) 0.0121(3) -0.0021(3) I1 0.0214(3) 0.0333(3) 0.0220(2) -0.00054(14) 0.01319(19) 0.00557(14) I2 0.0199(3) 0.0268(2) 0.0215(2) 0.00227(13) 0.00362(18) 0.00283(13) C1 0.019(3) 0.040(3) 0.018(3) -0.006(2) 0.007(2) 0.003(3) C2 0.020(3) 0.038(3) 0.022(3) -0.007(2) 0.006(2) -0.005(2) C3 0.020(3) 0.022(3) 0.018(3) 0.001(2) 0.004(2) 0.008(2) C4 0.033(3) 0.031(3) 0.024(3) -0.007(2) 0.016(3) 0.003(3) C5 0.027(3) 0.039(3) 0.028(3) 0.000(3) 0.016(3) -0.005(3) C6 0.021(3) 0.037(3) 0.028(3) -0.006(3) 0.006(3) 0.003(3) C7 0.018(3) 0.023(3) 0.029(3) 0.001(2) -0.002(2) 0.002(2) C8 0.029(4) 0.019(3) 0.036(3) -0.003(2) -0.001(3) 0.005(2) C9 0.021(3) 0.041(3) 0.028(3) 0.012(3) 0.008(3) -0.003(3) C10 0.021(3) 0.054(4) 0.024(3) 0.017(3) 0.006(3) -0.005(3) C11 0.022(3) 0.038(3) 0.027(3) 0.005(3) 0.014(3) -0.005(3) C12 0.011(3) 0.045(4) 0.028(3) 0.010(3) 0.004(2) -0.001(2) C13 0.020(3) 0.048(4) 0.024(3) 0.011(3) 0.006(3) -0.006(3) C14 0.016(3) 0.069(5) 0.035(4) 0.021(3) 0.012(3) -0.003(3) C15 0.028(3) 0.027(3) 0.031(3) 0.007(2) 0.019(3) 0.005(2) C16 0.034(4) 0.023(3) 0.042(4) -0.002(3) 0.014(3) -0.006(3) N1 0.013(2) 0.024(2) 0.022(2) -0.0037(18) 0.0057(19) -0.0026(18) N2 0.016(3) 0.037(3) 0.024(3) 0.006(2) 0.009(2) -0.0045(19) N3 0.012(2) 0.039(3) 0.027(3) 0.011(2) 0.007(2) -0.001(2) N4 0.018(2) 0.025(2) 0.026(2) -0.003(2) 0.000(2) -0.002(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 N1 2.037(5) . ? Cu1 Cu2 2.6043(10) 2_656 ? Cu1 I1 2.6271(8) . ? Cu1 I1 2.7082(8) 2_656 ? Cu1 I2 2.7409(8) . ? Cu1 Cu1 2.7544(15) 2_656 ? Cu1 Cu2 2.7646(10) . ? Cu2 N2 2.021(5) . ? Cu2 Cu2 2.5966(14) 2_656 ? Cu2 Cu1 2.6043(10) 2_656 ? Cu2 I2 2.6379(8) . ? Cu2 I2 2.7434(8) 2_656 ? Cu2 I1 2.7525(8) . ? I1 Cu1 2.7082(8) 2_656 ? I2 Cu2 2.7434(8) 2_656 ? C1 N1 1.344(7) . ? C1 C2 1.371(8) . ? C1 H1 0.9500 . ? C2 C3 1.398(8) . ? C2 H2 0.9500 . ? C3 C4 1.365(8) . ? C3 C6 1.508(8) . ? C4 C5 1.388(9) . ? C4 H4 0.9500 . ? C5 N1 1.343(7) . ? C5 H5 0.9500 . ? C6 N4 1.453(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N4 1.479(7) . ? C7 C7 1.482(12) 2 ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N4 1.444(7) . ? C8 C8 1.507(13) 2 ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.341(7) . ? C9 C10 1.375(8) . ? C9 H9 0.9500 . ? C10 C11 1.393(9) . ? C10 H10 0.9500 . ? C11 C12 1.390(8) . ? C11 C14 1.526(8) . ? C12 C13 1.388(8) . ? C12 H12 0.9500 . ? C13 N2 1.333(8) . ? C13 H13 0.9500 . ? C14 N3 1.460(8) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 N3 1.461(8) . ? C15 C15 1.524(12) 2_756 ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N3 1.465(8) . ? C16 C16 1.503(13) 2_756 ? C16 H16A 0.9900 . ? C16 H16B 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 N1 Cu1 Cu2 135.32(13) . 2_656 ? N1 Cu1 I1 112.94(13) . . ? Cu2 Cu1 I1 111.74(3) 2_656 . ? N1 Cu1 I1 101.61(13) . 2_656 ? Cu2 Cu1 I1 62.38(2) 2_656 2_656 ? I1 Cu1 I1 109.50(3) . 2_656 ? N1 Cu1 I2 105.07(14) . . ? Cu2 Cu1 I2 61.70(2) 2_656 . ? I1 Cu1 I2 106.57(3) . . ? I1 Cu1 I2 121.17(3) 2_656 . ? N1 Cu1 Cu1 146.67(13) . 2_656 ? Cu2 Cu1 Cu1 62.04(3) 2_656 2_656 ? I1 Cu1 Cu1 60.37(3) . 2_656 ? I1 Cu1 Cu1 57.49(2) 2_656 2_656 ? I2 Cu1 Cu1 108.064(18) . 2_656 ? N1 Cu1 Cu2 153.50(13) . . ? Cu2 Cu1 Cu2 57.75(3) 2_656 . ? I1 Cu1 Cu2 61.33(2) . . ? I1 Cu1 Cu2 104.60(3) 2_656 . ? I2 Cu1 Cu2 57.26(2) . . ? Cu1 Cu1 Cu2 56.31(2) 2_656 . ? N2 Cu2 Cu2 154.45(15) . 2_656 ? N2 Cu2 Cu1 127.87(15) . 2_656 ? Cu2 Cu2 Cu1 64.22(3) 2_656 2_656 ? N2 Cu2 I2 115.25(15) . . ? Cu2 Cu2 I2 63.21(3) 2_656 . ? Cu1 Cu2 I2 116.08(3) 2_656 . ? N2 Cu2 I2 104.15(15) . 2_656 ? Cu2 Cu2 I2 59.13(3) 2_656 2_656 ? Cu1 Cu2 I2 61.60(2) 2_656 2_656 ? I2 Cu2 I2 114.20(3) . 2_656 ? N2 Cu2 I1 96.96(15) . . ? Cu2 Cu2 I1 108.067(17) 2_656 . ? Cu1 Cu2 I1 60.66(2) 2_656 . ? I2 Cu2 I1 105.93(3) . . ? I2 Cu2 I1 119.46(3) 2_656 . ? N2 Cu2 Cu1 146.03(15) . . ? Cu2 Cu2 Cu1 58.02(3) 2_656 . ? Cu1 Cu2 Cu1 61.64(3) 2_656 . ? I2 Cu2 Cu1 60.92(2) . . ? I2 Cu2 Cu1 107.70(3) 2_656 . ? I1 Cu2 Cu1 56.87(2) . . ? Cu1 I1 Cu1 62.14(3) . 2_656 ? Cu1 I1 Cu2 61.80(2) . . ? Cu1 I1 Cu2 56.96(2) 2_656 . ? Cu2 I2 Cu1 61.82(2) . . ? Cu2 I2 Cu2 57.66(3) . 2_656 ? Cu1 I2 Cu2 56.70(2) . 2_656 ? N1 C1 C2 123.9(5) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C1 C2 C3 119.2(5) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 117.4(5) . . ? C4 C3 C6 120.3(5) . . ? C2 C3 C6 122.3(5) . . ? C3 C4 C5 120.2(5) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? N1 C5 C4 122.8(5) . . ? N1 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? N4 C6 C3 113.3(5) . . ? N4 C6 H6A 108.9 . . ? C3 C6 H6A 108.9 . . ? N4 C6 H6B 108.9 . . ? C3 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N4 C7 C7 110.8(4) . 2 ? N4 C7 H7A 109.5 . . ? C7 C7 H7A 109.5 2 . ? N4 C7 H7B 109.5 . . ? C7 C7 H7B 109.5 2 . ? H7A C7 H7B 108.1 . . ? N4 C8 C8 110.9(5) . 2 ? N4 C8 H8A 109.5 . . ? C8 C8 H8A 109.5 2 . ? N4 C8 H8B 109.5 . . ? C8 C8 H8B 109.5 2 . ? H8A C8 H8B 108.0 . . ? N2 C9 C10 122.7(6) . . ? N2 C9 H9 118.6 . . ? C10 C9 H9 118.6 . . ? C9 C10 C11 120.3(6) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C12 116.9(5) . . ? C10 C11 C14 119.8(5) . . ? C12 C11 C14 123.2(6) . . ? C13 C12 C11 119.2(6) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? N2 C13 C12 123.5(6) . . ? N2 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? N3 C14 C11 113.5(5) . . ? N3 C14 H14A 108.9 . . ? C11 C14 H14A 108.9 . . ? N3 C14 H14B 108.9 . . ? C11 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? N3 C15 C15 110.4(4) . 2_756 ? N3 C15 H15A 109.6 . . ? C15 C15 H15A 109.6 2_756 . ? N3 C15 H15B 109.6 . . ? C15 C15 H15B 109.6 2_756 . ? H15A C15 H15B 108.1 . . ? N3 C16 C16 110.1(5) . 2_756 ? N3 C16 H16A 109.6 . . ? C16 C16 H16A 109.6 2_756 . ? N3 C16 H16B 109.6 . . ? C16 C16 H16B 109.6 2_756 . ? H16A C16 H16B 108.1 . . ? C1 N1 C5 116.5(5) . . ? C1 N1 Cu1 120.6(4) . . ? C5 N1 Cu1 122.9(4) . . ? C13 N2 C9 117.3(5) . . ? C13 N2 Cu2 120.3(4) . . ? C9 N2 Cu2 122.1(4) . . ? C14 N3 C15 111.9(5) . . ? C14 N3 C16 112.3(6) . . ? C15 N3 C16 109.6(5) . . ? C8 N4 C6 114.3(5) . . ? C8 N4 C7 108.5(5) . . ? C6 N4 C7 112.5(5) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.277 _refine_diff_density_min -1.869 _refine_diff_density_rms 0.335 _database_code_depnum_ccdc_archive 'CCDC 959784' ####################################################################### # # 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_p1-298K _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 Cu2 I2 N4' _chemical_formula_weight 649.24 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.4183(15) _cell_length_b 19.1626(16) _cell_length_c 12.2780(10) _cell_angle_alpha 90.00 _cell_angle_beta 114.6330(10) _cell_angle_gamma 90.00 _cell_volume 3939.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.190 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 5.300 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.2993 _exptl_absorpt_correction_T_max 0.5688 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8555 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3795 _reflns_number_gt 3174 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0297P)^2^+1.8445P] 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 3795 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0654 _refine_ls_wR_factor_gt 0.0620 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 0.43525(3) 0.15155(3) 0.64017(5) 0.04723(14) Uani 1 1 d . . . Cu2 Cu 0.55502(3) 0.25192(3) 0.70944(5) 0.05064(15) Uani 1 1 d . . . I1 I 0.576790(16) 0.116119(15) 0.65480(2) 0.04422(9) Uani 1 1 d . . . I2 I 0.409771(16) 0.286565(14) 0.55718(2) 0.04477(9) Uani 1 1 d . . . C1 C 0.2782(2) 0.0831(2) 0.5291(4) 0.0440(10) Uani 1 1 d . . . H1 H 0.2728 0.1027 0.5946 0.053 Uiso 1 1 calc R . . C2 C 0.2158(2) 0.0437(2) 0.4500(4) 0.0463(10) Uani 1 1 d . . . H2 H 0.1706 0.0362 0.4640 0.056 Uiso 1 1 calc R . . C3 C 0.2210(2) 0.0156(2) 0.3499(4) 0.0407(9) Uani 1 1 d . . . C4 C 0.2900(3) 0.0287(2) 0.3361(4) 0.0504(11) Uani 1 1 d . . . H4 H 0.2960 0.0114 0.2695 0.060 Uiso 1 1 calc R . . C5 C 0.3500(3) 0.0670(2) 0.4198(4) 0.0487(11) Uani 1 1 d . . . H5 H 0.3964 0.0741 0.4085 0.058 Uiso 1 1 calc R . . C6 C 0.1562(3) -0.0300(2) 0.2627(4) 0.0559(12) Uani 1 1 d . . . H6A H 0.1435 -0.0139 0.1819 0.067 Uiso 1 1 calc R . . H6B H 0.1762 -0.0774 0.2692 0.067 Uiso 1 1 calc R . . C7 C 0.0349(3) 0.0315(2) 0.2334(4) 0.0506(11) Uani 1 1 d . . . H7A H 0.0157 0.0320 0.1469 0.061 Uiso 1 1 calc R . . H7B H 0.0668 0.0731 0.2650 0.061 Uiso 1 1 calc R . . C8 C 0.0352(3) -0.0924(2) 0.2341(4) 0.0579(13) Uani 1 1 d . . . H8A H 0.0672 -0.1339 0.2666 0.069 Uiso 1 1 calc R . . H8B H 0.0167 -0.0934 0.1477 0.069 Uiso 1 1 calc R . . C9 C 0.6317(2) 0.3308(2) 0.5787(4) 0.0519(12) Uani 1 1 d . . . H9 H 0.5792 0.3412 0.5272 0.062 Uiso 1 1 calc R . . C10 C 0.6919(3) 0.3530(3) 0.5486(4) 0.0522(12) Uani 1 1 d . . . H10 H 0.6796 0.3769 0.4773 0.063 Uiso 1 1 calc R . . C11 C 0.7704(2) 0.3397(2) 0.6241(4) 0.0449(10) Uani 1 1 d . . . C12 C 0.7841(2) 0.3035(2) 0.7282(4) 0.0513(11) Uani 1 1 d . . . H12 H 0.8360 0.2929 0.7819 0.062 Uiso 1 1 calc R . . C13 C 0.7208(3) 0.2834(2) 0.7517(4) 0.0531(12) Uani 1 1 d . . . H13 H 0.7313 0.2601 0.8232 0.064 Uiso 1 1 calc R . . C14 C 0.8365(3) 0.3670(3) 0.5927(4) 0.0681(15) Uani 1 1 d . . . H14A H 0.8389 0.3386 0.5289 0.082 Uiso 1 1 calc R . . H14B H 0.8236 0.4143 0.5627 0.082 Uiso 1 1 calc R . . C15 C 0.9607(2) 0.4285(2) 0.6951(4) 0.0456(10) Uani 1 1 d . . . H15A H 0.9303 0.4698 0.6952 0.055 Uiso 1 1 calc R . . H15B H 0.9706 0.4295 0.6234 0.055 Uiso 1 1 calc R . . C16 C 0.9610(3) 0.3049(2) 0.6956(4) 0.0576(12) Uani 1 1 d . . . H16A H 0.9709 0.3036 0.6239 0.069 Uiso 1 1 calc R . . H16B H 0.9306 0.2636 0.6960 0.069 Uiso 1 1 calc R . . N1 N 0.34585(19) 0.09477(17) 0.5171(3) 0.0382(8) Uani 1 1 d . . . N2 N 0.6450(2) 0.29520(18) 0.6777(3) 0.0443(8) Uani 1 1 d . . . N3 N 0.9153(2) 0.36692(19) 0.6941(3) 0.0458(9) Uani 1 1 d . . . N4 N 0.0839(2) -0.03052(17) 0.2821(3) 0.0462(9) Uani 1 1 d . . . 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 0.0363(3) 0.0560(3) 0.0485(3) -0.0118(3) 0.0168(3) -0.0082(2) Cu2 0.0345(3) 0.0635(4) 0.0566(3) 0.0149(3) 0.0217(3) -0.0044(3) I1 0.03979(17) 0.05604(18) 0.04235(16) -0.00070(12) 0.02261(13) 0.00875(13) I2 0.03787(17) 0.04625(16) 0.04109(16) 0.00376(12) 0.00742(13) 0.00491(13) C1 0.037(2) 0.055(3) 0.040(2) -0.011(2) 0.0151(19) -0.001(2) C2 0.027(2) 0.065(3) 0.045(2) -0.007(2) 0.0131(19) -0.006(2) C3 0.035(2) 0.040(2) 0.039(2) -0.0035(18) 0.0064(18) 0.0101(18) C4 0.055(3) 0.056(3) 0.044(2) -0.010(2) 0.024(2) 0.005(2) C5 0.042(3) 0.061(3) 0.047(3) -0.010(2) 0.021(2) -0.006(2) C6 0.049(3) 0.055(3) 0.051(3) -0.013(2) 0.008(2) 0.003(2) C7 0.049(3) 0.041(2) 0.051(3) 0.001(2) 0.010(2) -0.002(2) C8 0.045(3) 0.038(2) 0.065(3) -0.006(2) -0.003(2) 0.002(2) C9 0.027(2) 0.071(3) 0.050(3) 0.020(2) 0.008(2) -0.005(2) C10 0.036(3) 0.079(3) 0.038(2) 0.019(2) 0.011(2) -0.006(2) C11 0.032(2) 0.063(3) 0.039(2) 0.010(2) 0.0136(19) -0.006(2) C12 0.024(2) 0.076(3) 0.048(3) 0.017(2) 0.0091(19) -0.004(2) C13 0.036(3) 0.073(3) 0.047(3) 0.021(2) 0.015(2) -0.005(2) C14 0.034(3) 0.108(4) 0.060(3) 0.028(3) 0.018(2) -0.009(3) C15 0.046(3) 0.048(2) 0.050(3) 0.007(2) 0.027(2) 0.005(2) C16 0.059(3) 0.043(2) 0.066(3) -0.001(2) 0.022(2) -0.013(2) N1 0.0310(18) 0.0418(18) 0.0409(19) -0.0027(15) 0.0139(16) 0.0003(15) N2 0.032(2) 0.056(2) 0.044(2) 0.0118(17) 0.0143(17) -0.0065(16) N3 0.0294(19) 0.059(2) 0.051(2) 0.0098(18) 0.0187(17) -0.0029(17) N4 0.031(2) 0.0402(19) 0.051(2) -0.0061(16) 0.0005(16) -0.0011(15) _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 N1 2.026(3) . y Cu1 Cu2 2.6203(8) 2_656 ? Cu1 I1 2.6265(6) . y Cu1 I1 2.7043(6) 2_656 y Cu1 I2 2.7484(7) . y Cu1 Cu1 2.7568(11) 2_656 ? Cu1 Cu2 2.7794(8) . ? Cu2 N2 2.030(3) . y Cu2 Cu2 2.6044(10) 2_656 ? Cu2 Cu1 2.6203(7) 2_656 ? Cu2 I2 2.6312(6) . y Cu2 I2 2.7429(7) 2_656 y Cu2 I1 2.7581(7) . y I1 Cu1 2.7043(6) 2_656 ? I2 Cu2 2.7429(7) 2_656 ? C1 N1 1.332(5) . ? C1 C2 1.380(6) . ? C1 H1 0.9300 . ? C2 C3 1.382(5) . ? C2 H2 0.9300 . ? C3 C4 1.374(6) . ? C3 C6 1.505(6) . ? C4 C5 1.367(6) . ? C4 H4 0.9300 . ? C5 N1 1.340(5) . ? C5 H5 0.9300 . ? C6 N4 1.447(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N4 1.462(5) . ? C7 C7 1.500(8) 2 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N4 1.455(5) . ? C8 C8 1.503(9) 2 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.324(5) . ? C9 C10 1.374(5) . ? C9 H9 0.9300 . ? C10 C11 1.377(6) . ? C10 H10 0.9300 . ? C11 C12 1.382(5) . ? C11 C14 1.515(5) . ? C12 C13 1.369(5) . ? C12 H12 0.9300 . ? C13 N2 1.330(5) . ? C13 H13 0.9300 . ? C14 N3 1.466(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N3 1.443(5) . ? C15 C15 1.513(8) 2_756 ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N3 1.452(5) . ? C16 C16 1.500(9) 2_756 ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? 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 N1 Cu1 Cu2 135.67(9) . 2_656 ? N1 Cu1 I1 112.79(9) . . y Cu2 Cu1 I1 111.54(2) 2_656 . ? N1 Cu1 I1 101.69(9) . 2_656 y Cu2 Cu1 I1 62.373(19) 2_656 2_656 ? I1 Cu1 I1 109.61(2) . 2_656 y N1 Cu1 I2 105.61(9) . . y Cu2 Cu1 I2 61.39(2) 2_656 . ? I1 Cu1 I2 106.26(2) . . y I1 Cu1 I2 120.92(2) 2_656 . y N1 Cu1 Cu1 146.34(9) . 2_656 ? Cu2 Cu1 Cu1 62.19(2) 2_656 2_656 ? I1 Cu1 Cu1 60.252(19) . 2_656 ? I1 Cu1 Cu1 57.485(19) 2_656 2_656 ? I2 Cu1 Cu1 107.886(13) . 2_656 ? N1 Cu1 Cu2 153.47(9) . . ? Cu2 Cu1 Cu2 57.58(2) 2_656 . ? I1 Cu1 Cu2 61.278(18) . . ? I1 Cu1 Cu2 104.56(2) 2_656 . ? I2 Cu1 Cu2 56.845(17) . . ? Cu1 Cu1 Cu2 56.495(18) 2_656 . ? N2 Cu2 Cu2 154.24(10) . 2_656 ? N2 Cu2 Cu1 127.84(10) . 2_656 ? Cu2 Cu2 Cu1 64.28(2) 2_656 2_656 ? N2 Cu2 I2 115.47(10) . . y Cu2 Cu2 I2 63.18(2) 2_656 . ? Cu1 Cu2 I2 115.88(2) 2_656 . ? N2 Cu2 I2 104.18(10) . 2_656 y Cu2 Cu2 I2 58.89(2) 2_656 2_656 ? Cu1 Cu2 I2 61.606(19) 2_656 2_656 ? I2 Cu2 I2 114.13(2) . 2_656 y N2 Cu2 I1 97.23(10) . . y Cu2 Cu2 I1 107.952(12) 2_656 . ? Cu1 Cu2 I1 60.306(19) 2_656 . ? I2 Cu2 I1 105.85(2) . . y I2 Cu2 I1 119.17(2) 2_656 . y N2 Cu2 Cu1 146.21(11) . . ? Cu2 Cu2 Cu1 58.139(19) 2_656 . ? Cu1 Cu2 Cu1 61.32(3) 2_656 . ? I2 Cu2 Cu1 60.985(18) . . ? I2 Cu2 Cu1 107.40(2) 2_656 . ? I1 Cu2 Cu1 56.627(17) . . ? Cu1 I1 Cu1 62.26(2) . 2_656 ? Cu1 I1 Cu2 62.095(17) . . ? Cu1 I1 Cu2 57.321(16) 2_656 . ? Cu2 I2 Cu2 57.930(19) . 2_656 ? Cu2 I2 Cu1 62.170(17) . . ? Cu2 I2 Cu1 57.001(17) 2_656 . ? N1 C1 C2 123.9(4) . . ? N1 C1 H1 118.1 . . ? C2 C1 H1 118.1 . . ? C1 C2 C3 119.6(4) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 116.6(4) . . ? C4 C3 C6 121.2(4) . . ? C2 C3 C6 122.1(4) . . ? C5 C4 C3 120.4(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? N1 C5 C4 123.7(4) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? N4 C6 C3 113.4(4) . . ? N4 C6 H6A 108.9 . . ? C3 C6 H6A 108.9 . . ? N4 C6 H6B 108.9 . . ? C3 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N4 C7 C7 110.0(3) . 2 ? N4 C7 H7A 109.7 . . ? C7 C7 H7A 109.7 2 . ? N4 C7 H7B 109.7 . . ? C7 C7 H7B 109.7 2 . ? H7A C7 H7B 108.2 . . ? N4 C8 C8 110.4(3) . 2 ? N4 C8 H8A 109.6 . . ? C8 C8 H8A 109.6 2 . ? N4 C8 H8B 109.6 . . ? C8 C8 H8B 109.6 2 . ? H8A C8 H8B 108.1 . . ? N2 C9 C10 123.1(4) . . ? N2 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? C11 C10 C9 120.1(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 116.7(4) . . ? C10 C11 C14 119.7(4) . . ? C12 C11 C14 123.5(4) . . ? C13 C12 C11 119.6(4) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? N2 C13 C12 123.5(4) . . ? N2 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? N3 C14 C11 113.6(4) . . ? N3 C14 H14A 108.9 . . ? C11 C14 H14A 108.9 . . ? N3 C14 H14B 108.9 . . ? C11 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? N3 C15 C15 110.1(3) . 2_756 ? N3 C15 H15A 109.6 . . ? C15 C15 H15A 109.6 2_756 . ? N3 C15 H15B 109.6 . . ? C15 C15 H15B 109.6 2_756 . ? H15A C15 H15B 108.2 . . ? N3 C16 C16 110.2(3) . 2_756 ? N3 C16 H16A 109.6 . . ? C16 C16 H16A 109.6 2_756 . ? N3 C16 H16B 109.6 . . ? C16 C16 H16B 109.6 2_756 . ? H16A C16 H16B 108.1 . . ? C1 N1 C5 115.8(3) . . ? C1 N1 Cu1 121.0(3) . . ? C5 N1 Cu1 123.2(3) . . ? C9 N2 C13 117.0(4) . . ? C9 N2 Cu2 122.2(3) . . ? C13 N2 Cu2 120.5(3) . . ? C15 N3 C16 109.8(3) . . ? C15 N3 C14 111.7(3) . . ? C16 N3 C14 112.0(4) . . ? C6 N4 C8 113.1(3) . . ? C6 N4 C7 112.4(3) . . ? C8 N4 C7 109.0(3) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.580 _refine_diff_density_min -0.657 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 959785' ####################################################################### # # 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_p2-298K _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 Cu2 I2 N6' _chemical_formula_weight 783.42 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' 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 17.9843(18) _cell_length_b 14.9569(14) _cell_length_c 22.464(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.631(2) _cell_angle_gamma 90.00 _cell_volume 5617.1(9) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3040 _exptl_absorpt_coefficient_mu 3.736 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6042 _exptl_absorpt_correction_T_max 0.7543 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13763 _diffrn_reflns_av_R_equivalents 0.1046 _diffrn_reflns_av_sigmaI/netI 0.0993 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4934 _reflns_number_gt 2949 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0274P)^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 4934 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0800 _refine_ls_goodness_of_fit_ref 0.856 _refine_ls_restrained_S_all 0.856 _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 0.24761(5) 0.32473(6) 0.35732(4) 0.0558(3) Uani 1 1 d . . . Cu2 Cu 0.19532(5) 0.21701(6) 0.43131(4) 0.0604(3) Uani 1 1 d . . . I1 I 0.23356(3) 0.38859(3) 0.46447(2) 0.05105(16) Uani 1 1 d . . . I2 I 0.22908(3) 0.15105(3) 0.33473(2) 0.05892(17) Uani 1 1 d . . . C1 C 0.3946(5) 0.3281(7) 0.3243(4) 0.109(4) Uani 1 1 d . . . H1 H 0.3620 0.2932 0.2904 0.130 Uiso 1 1 calc R . . C2 C 0.4721(5) 0.3433(8) 0.3287(4) 0.110(4) Uani 1 1 d . . . H2 H 0.4909 0.3173 0.2993 0.133 Uiso 1 1 calc R . . C3 C 0.5214(4) 0.3971(5) 0.3768(4) 0.058(2) Uani 1 1 d . . . C4 C 0.4900(4) 0.4301(5) 0.4179(4) 0.060(2) Uani 1 1 d . . . H4 H 0.5211 0.4666 0.4513 0.072 Uiso 1 1 calc R . . C5 C 0.4111(4) 0.4103(5) 0.4114(4) 0.058(2) Uani 1 1 d . . . H5 H 0.3920 0.4340 0.4413 0.070 Uiso 1 1 calc R . . C6 C 0.6076(4) 0.4187(5) 0.3829(4) 0.079(3) Uani 1 1 d . . . H6A H 0.6065 0.4677 0.3543 0.094 Uiso 1 1 calc R . . H6B H 0.6377 0.4384 0.4263 0.094 Uiso 1 1 calc R . . C7 C 0.6599(4) 0.2706(5) 0.4130(3) 0.0540(19) Uani 1 1 d . . . H7A H 0.6083 0.2499 0.4119 0.065 Uiso 1 1 calc R . . H7B H 0.6902 0.2917 0.4560 0.065 Uiso 1 1 calc R . . C8 C 0.7043(4) 0.1935(5) 0.3967(4) 0.060(2) Uani 1 1 d . . . H8A H 0.7108 0.1451 0.4269 0.072 Uiso 1 1 calc R . . H8B H 0.6733 0.1713 0.3541 0.072 Uiso 1 1 calc R . . C9 C 0.7715(4) 0.2965(5) 0.3542(3) 0.0532(19) Uani 1 1 d . . . H9A H 0.7413 0.2755 0.3111 0.064 Uiso 1 1 calc R . . H9B H 0.8231 0.3172 0.3553 0.064 Uiso 1 1 calc R . . C10 C 0.7274(4) 0.3735(5) 0.3697(4) 0.065(2) Uani 1 1 d . . . H10A H 0.7585 0.3967 0.4119 0.078 Uiso 1 1 calc R . . H10B H 0.7203 0.4212 0.3388 0.078 Uiso 1 1 calc R . . C11 C 0.8248(4) 0.1468(5) 0.3828(4) 0.066(2) Uani 1 1 d . . . H11A H 0.7968 0.1304 0.3384 0.079 Uiso 1 1 calc R . . H11B H 0.8236 0.0958 0.4091 0.079 Uiso 1 1 calc R . . C12 C 1.0254(4) 0.1570(5) 0.3611(3) 0.0535(19) Uani 1 1 d . . . H12 H 1.0460 0.1370 0.3311 0.064 Uiso 1 1 calc R . . C13 C 0.9455(4) 0.1402(5) 0.3502(3) 0.0544(19) Uani 1 1 d . . . H13 H 0.9142 0.1092 0.3137 0.065 Uiso 1 1 calc R . . C14 C 0.9120(4) 0.1693(4) 0.3934(4) 0.0513(18) Uani 1 1 d . . . C15 C 0.9618(4) 0.2158(5) 0.4457(4) 0.059(2) Uani 1 1 d . . . H15 H 0.9420 0.2368 0.4760 0.070 Uiso 1 1 calc R . . C16 C 1.0417(4) 0.2321(5) 0.4544(3) 0.0539(19) Uani 1 1 d . . . H16 H 1.0734 0.2652 0.4897 0.065 Uiso 1 1 calc R . . C17 C 0.1649(5) 0.4782(6) 0.2767(4) 0.090(3) Uani 1 1 d . . . H17 H 0.2065 0.5086 0.3075 0.108 Uiso 1 1 calc R . . C18 C 0.1123(5) 0.5269(5) 0.2267(4) 0.092(3) Uani 1 1 d . . . H18 H 0.1188 0.5884 0.2247 0.110 Uiso 1 1 calc R . . C19 C 0.0503(4) 0.4845(5) 0.1799(3) 0.0438(17) Uani 1 1 d . . . C20 C 0.0427(4) 0.3950(5) 0.1874(3) 0.0530(18) Uani 1 1 d . . . H20 H 0.0006 0.3635 0.1579 0.064 Uiso 1 1 calc R . . C21 C 0.0980(4) 0.3510(5) 0.2393(3) 0.0468(17) Uani 1 1 d . . . H21 H 0.0910 0.2900 0.2431 0.056 Uiso 1 1 calc R . . C22 C -0.0070(4) 0.5336(5) 0.1216(3) 0.060(2) Uani 1 1 d . . . H22A H -0.0607 0.5302 0.1218 0.071 Uiso 1 1 calc R . . H22B H 0.0081 0.5961 0.1240 0.071 Uiso 1 1 calc R . . C23 C 0.0709(3) 0.5080(5) 0.0542(3) 0.054(2) Uani 1 1 d . . . H23A H 0.1133 0.4821 0.0906 0.065 Uiso 1 1 calc R . . H23B H 0.0816 0.5714 0.0531 0.065 Uiso 1 1 calc R . . C24 C -0.0703(4) 0.5348(5) 0.0059(3) 0.0514(19) Uani 1 1 d . . . H24A H -0.0615 0.5986 0.0043 0.062 Uiso 1 1 calc R . . H24B H -0.1217 0.5260 0.0099 0.062 Uiso 1 1 calc R . . N1 N 0.3630(3) 0.3601(4) 0.3654(3) 0.0581(16) Uani 1 1 d . . . N2 N 0.6486(3) 0.3430(4) 0.3681(3) 0.0517(15) Uani 1 1 d . . . N3 N 0.7832(3) 0.2230(4) 0.3990(3) 0.0460(14) Uani 1 1 d . . . N4 N 1.0741(3) 0.2009(4) 0.4129(3) 0.0473(14) Uani 1 1 d . . . N5 N 0.1596(3) 0.3895(4) 0.2834(2) 0.0454(14) Uani 1 1 d . . . N6 N -0.0062(3) 0.4955(4) 0.0620(2) 0.0471(14) Uani 1 1 d . . . 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 0.0358(5) 0.0780(7) 0.0482(5) 0.0022(5) 0.0090(4) 0.0041(5) Cu2 0.0430(5) 0.0779(7) 0.0611(6) 0.0051(5) 0.0200(5) 0.0050(5) I1 0.0494(3) 0.0616(3) 0.0418(3) 0.0030(2) 0.0164(2) 0.0095(2) I2 0.0596(3) 0.0661(4) 0.0516(3) 0.0041(3) 0.0212(3) 0.0152(3) C1 0.047(5) 0.218(12) 0.062(6) -0.064(7) 0.021(5) -0.030(6) C2 0.047(6) 0.207(12) 0.087(7) -0.066(7) 0.036(5) -0.016(7) C3 0.029(4) 0.073(6) 0.073(5) 0.000(5) 0.020(4) 0.009(4) C4 0.034(4) 0.068(5) 0.071(5) -0.016(4) 0.013(4) -0.008(4) C5 0.052(5) 0.062(5) 0.071(5) -0.018(4) 0.034(4) -0.004(4) C6 0.039(5) 0.068(6) 0.125(8) -0.006(5) 0.026(5) -0.008(4) C7 0.038(4) 0.063(5) 0.066(5) -0.004(4) 0.025(4) -0.006(4) C8 0.041(4) 0.064(5) 0.077(5) 0.013(4) 0.022(4) -0.012(4) C9 0.034(4) 0.067(5) 0.064(5) 0.010(4) 0.024(4) 0.002(4) C10 0.038(4) 0.069(5) 0.097(6) 0.007(5) 0.035(4) 0.002(4) C11 0.044(5) 0.056(5) 0.096(6) 0.000(5) 0.024(4) -0.008(4) C12 0.043(5) 0.061(5) 0.055(5) -0.008(4) 0.017(4) -0.003(4) C13 0.047(5) 0.054(5) 0.054(5) -0.005(4) 0.009(4) -0.003(4) C14 0.039(4) 0.043(4) 0.066(5) -0.001(4) 0.013(4) 0.004(3) C15 0.046(5) 0.066(5) 0.068(5) -0.006(4) 0.027(4) 0.006(4) C16 0.037(4) 0.062(5) 0.060(5) -0.009(4) 0.015(4) 0.002(4) C17 0.081(7) 0.069(6) 0.073(6) 0.016(5) -0.027(5) -0.032(5) C18 0.096(7) 0.054(5) 0.079(6) 0.016(5) -0.022(5) -0.018(5) C19 0.047(4) 0.050(5) 0.033(4) 0.005(3) 0.013(3) 0.007(4) C20 0.046(4) 0.052(5) 0.047(4) -0.003(4) 0.002(4) -0.008(4) C21 0.047(4) 0.044(4) 0.040(4) 0.007(3) 0.004(4) 0.001(4) C22 0.061(5) 0.061(5) 0.058(5) 0.016(4) 0.023(4) 0.009(4) C23 0.021(4) 0.091(6) 0.041(4) 0.020(4) 0.000(3) 0.003(4) C24 0.030(4) 0.074(5) 0.042(4) 0.022(4) 0.004(3) 0.007(3) N1 0.038(4) 0.088(5) 0.047(4) -0.004(3) 0.014(3) 0.004(3) N2 0.033(3) 0.051(4) 0.073(4) 0.002(3) 0.023(3) 0.001(3) N3 0.028(3) 0.048(4) 0.061(4) 0.000(3) 0.015(3) -0.003(3) N4 0.037(3) 0.053(4) 0.047(3) 0.008(3) 0.010(3) 0.010(3) N5 0.036(3) 0.056(4) 0.038(3) -0.001(3) 0.007(3) -0.008(3) N6 0.032(3) 0.070(4) 0.034(3) 0.018(3) 0.007(3) 0.006(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 Cu1 N5 2.065(5) . y Cu1 N1 2.084(5) . y Cu1 I2 2.6442(11) . y Cu1 I1 2.6868(9) . y Cu1 Cu2 2.7195(12) . ? Cu2 N4 2.078(5) 1_455 y Cu2 I2 2.6495(10) . y Cu2 I1 2.6900(11) . y Cu2 I1 2.7211(10) 7_556 y I1 Cu2 2.7211(10) 7_556 ? C1 N1 1.338(9) . ? C1 C2 1.379(10) . ? C1 H1 0.9300 . ? C2 C3 1.377(11) . ? C2 H2 0.9300 . ? C3 C4 1.343(9) . ? C3 C6 1.539(9) . ? C4 C5 1.403(8) . ? C4 H4 0.9300 . ? C5 N1 1.312(8) . ? C5 H5 0.9300 . ? C6 N2 1.455(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N2 1.442(8) . ? C7 C8 1.523(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N3 1.468(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N3 1.453(8) . ? C9 C10 1.510(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.476(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N3 1.481(8) . ? C11 C14 1.534(9) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N4 1.342(8) . ? C12 C13 1.388(8) . ? C12 H12 0.9300 . ? C13 C14 1.389(9) . ? C13 H13 0.9300 . ? C14 C15 1.375(9) . ? C15 C16 1.399(8) . ? C15 H15 0.9300 . ? C16 N4 1.351(8) . ? C16 H16 0.9300 . ? C17 N5 1.343(9) . ? C17 C18 1.380(10) . ? C17 H17 0.9300 . ? C18 C19 1.373(9) . ? C18 H18 0.9300 . ? C19 C20 1.363(8) . ? C19 C22 1.523(9) . ? C20 C21 1.387(8) . ? C20 H20 0.9300 . ? C21 N5 1.316(7) . ? C21 H21 0.9300 . ? C22 N6 1.459(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 N6 1.472(7) . ? C23 C24 1.491(9) 5_565 ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 N6 1.480(7) . ? C24 C23 1.491(9) 5_565 ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? N4 Cu2 2.078(5) 1_655 ? 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 N5 Cu1 N1 113.3(2) . . y N5 Cu1 I2 107.55(16) . . y N1 Cu1 I2 108.49(18) . . y N5 Cu1 I1 104.84(15) . . y N1 Cu1 I1 104.55(17) . . y I2 Cu1 I1 118.32(4) . . y N5 Cu1 Cu2 115.71(15) . . ? N1 Cu1 Cu2 130.90(16) . . ? I2 Cu1 Cu2 59.19(3) . . ? I1 Cu1 Cu2 59.68(3) . . ? N4 Cu2 I2 109.52(16) 1_455 . y N4 Cu2 I1 107.95(16) 1_455 . y I2 Cu2 I1 118.01(3) . . y N4 Cu2 Cu1 121.38(15) 1_455 . ? I2 Cu2 Cu1 58.99(3) . . ? I1 Cu2 Cu1 59.56(3) . . ? N4 Cu2 I1 103.30(14) 1_455 7_556 y I2 Cu2 I1 108.15(3) . 7_556 y I1 Cu2 I1 108.93(3) . 7_556 y Cu1 Cu2 I1 135.32(4) . 7_556 ? Cu1 I1 Cu2 60.76(3) . . ? Cu1 I1 Cu2 113.26(3) . 7_556 ? Cu2 I1 Cu2 71.07(3) . 7_556 ? Cu1 I2 Cu2 61.82(3) . . ? N1 C1 C2 124.5(8) . . ? N1 C1 H1 117.7 . . ? C2 C1 H1 117.7 . . ? C3 C2 C1 119.6(7) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 116.3(7) . . ? C4 C3 C6 121.7(7) . . ? C2 C3 C6 122.0(7) . . ? C3 C4 C5 121.1(7) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? N1 C5 C4 123.4(6) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? N2 C6 C3 113.2(6) . . ? N2 C6 H6A 108.9 . . ? C3 C6 H6A 108.9 . . ? N2 C6 H6B 108.9 . . ? C3 C6 H6B 108.9 . . ? H6A C6 H6B 107.8 . . ? N2 C7 C8 110.6(5) . . ? N2 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? N3 C8 C7 110.4(6) . . ? N3 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? N3 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N3 C9 C10 111.8(6) . . ? N3 C9 H9A 109.3 . . ? C10 C9 H9A 109.3 . . ? N3 C9 H9B 109.3 . . ? C10 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? N2 C10 C9 109.8(6) . . ? N2 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? N2 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N3 C11 C14 111.9(5) . . ? N3 C11 H11A 109.2 . . ? C14 C11 H11A 109.2 . . ? N3 C11 H11B 109.2 . . ? C14 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? N4 C12 C13 122.9(6) . . ? N4 C12 H12 118.5 . . ? C13 C12 H12 118.5 . . ? C12 C13 C14 120.5(7) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 116.2(6) . . ? C15 C14 C11 123.4(7) . . ? C13 C14 C11 120.4(7) . . ? C14 C15 C16 121.3(7) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? N4 C16 C15 121.7(6) . . ? N4 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? N5 C17 C18 123.9(7) . . ? N5 C17 H17 118.0 . . ? C18 C17 H17 118.0 . . ? C19 C18 C17 119.9(7) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C20 C19 C18 116.8(6) . . ? C20 C19 C22 120.8(6) . . ? C18 C19 C22 122.4(7) . . ? C19 C20 C21 119.7(6) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? N5 C21 C20 124.7(6) . . ? N5 C21 H21 117.6 . . ? C20 C21 H21 117.6 . . ? N6 C22 C19 111.7(5) . . ? N6 C22 H22A 109.3 . . ? C19 C22 H22A 109.3 . . ? N6 C22 H22B 109.3 . . ? C19 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? N6 C23 C24 111.2(5) . 5_565 ? N6 C23 H23A 109.4 . . ? C24 C23 H23A 109.4 5_565 . ? N6 C23 H23B 109.4 . . ? C24 C23 H23B 109.4 5_565 . ? H23A C23 H23B 108.0 . . ? N6 C24 C23 110.1(5) . 5_565 ? N6 C24 H24A 109.6 . . ? C23 C24 H24A 109.6 5_565 . ? N6 C24 H24B 109.6 . . ? C23 C24 H24B 109.6 5_565 . ? H24A C24 H24B 108.2 . . ? C5 N1 C1 115.1(6) . . ? C5 N1 Cu1 124.1(5) . . ? C1 N1 Cu1 120.8(5) . . ? C7 N2 C6 112.1(6) . . ? C7 N2 C10 109.1(5) . . ? C6 N2 C10 108.4(5) . . ? C9 N3 C8 108.2(5) . . ? C9 N3 C11 111.7(5) . . ? C8 N3 C11 109.2(5) . . ? C12 N4 C16 117.3(6) . . ? C12 N4 Cu2 122.1(5) . 1_655 ? C16 N4 Cu2 120.6(5) . 1_655 ? C21 N5 C17 115.0(6) . . ? C21 N5 Cu1 125.7(5) . . ? C17 N5 Cu1 119.3(5) . . ? C22 N6 C23 112.8(5) . . ? C22 N6 C24 111.1(5) . . ? C23 N6 C24 108.6(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.600 _refine_diff_density_min -0.901 _refine_diff_density_rms 0.132 _database_code_depnum_ccdc_archive 'CCDC 959786'