# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email fangzhenlan@fjirsm.ac.cn loop_ _publ_author_name 'Zhen-Lan Fang' 'Wenbin Yang' 'Jian-Gang He' 'Kaining Ding' 'Xiao-Yuan Wu' 'Qisheng Zhang' 'Rong-Min Yu' 'Can-Zhong Lu' _publ_contact_author_name 'Can-Zhong Lu' data_1 _database_code_depnum_ccdc_archive 'CCDC 762251' #TrackingRef '1-2-revised-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Cu4 I5 N5' _chemical_formula_weight 1169.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 10.366(9) _cell_length_b 11.154(9) _cell_length_c 12.483(10) _cell_angle_alpha 96.342(10) _cell_angle_beta 105.741(6) _cell_angle_gamma 104.400(4) _cell_volume 1320.9(19) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2846 _cell_measurement_theta_min 2.2907 _cell_measurement_theta_max 27.4449 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.939 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 9.034 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.239 _exptl_absorpt_correction_T_max 0.338 _exptl_absorpt_process_details ? _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 ? _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 7985 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4442 _reflns_number_gt 3189 _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^)+(0.0882P)^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 4442 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_ref 0.1462 _refine_ls_wR_factor_gt 0.1311 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _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 -0.08290(19) 0.71419(16) -0.16716(19) 0.0766(6) Uani 1 1 d . . . Cu2 Cu 0.0694(2) 0.49373(16) 0.10717(16) 0.0719(5) Uani 1 1 d . . . Cu3 Cu -0.10165(15) 0.19237(14) 0.26614(15) 0.0588(4) Uani 1 1 d . . . Cu4 Cu -0.10449(15) -0.00639(14) 0.41593(13) 0.0566(4) Uani 1 1 d . . . I1 I 0.06878(8) 0.71381(7) 0.06371(6) 0.0436(2) Uani 1 1 d . . . I2 I 0.32254(8) 0.45450(8) 0.19846(7) 0.0573(3) Uani 1 1 d . . . I3 I -0.04042(7) 0.43278(6) 0.28403(6) 0.0422(2) Uani 1 1 d . . . I4 I 0.05738(8) 0.06470(7) 0.21418(7) 0.0463(2) Uani 1 1 d . . . I5 I 0.03001(8) 0.20651(7) 0.55606(7) 0.0494(2) Uani 1 1 d . . . N1 N -0.5167(9) -0.0049(8) 0.2473(7) 0.038(2) Uani 1 1 d . . . N2 N -0.3002(8) 0.0760(8) 0.2609(7) 0.0392(15) Uani 1 1 d . . . N3 N -0.2958(8) 0.0083(8) 0.3286(7) 0.0392(15) Uani 1 1 d . . . N4 N -0.5875(10) -0.2821(9) 0.5315(8) 0.045(2) Uani 1 1 d . . . N5 N -0.5956(11) 0.2342(8) -0.0745(7) 0.048(2) Uani 1 1 d . . . C1 C -0.6687(15) -0.5007(12) 0.5540(11) 0.074(4) Uani 1 1 d . . . H1A H -0.7056 -0.5543 0.6023 0.111 Uiso 1 1 calc R . . H1B H -0.5792 -0.5128 0.5510 0.111 Uiso 1 1 calc R . . H1C H -0.7356 -0.5236 0.4773 0.111 Uiso 1 1 calc R . . C2 C -0.6475(16) -0.3691(12) 0.6003(11) 0.066(4) Uani 1 1 d . . . H2A H -0.5833 -0.3475 0.6791 0.079 Uiso 1 1 calc R . . H2B H -0.7383 -0.3571 0.6026 0.079 Uiso 1 1 calc R . . C3 C -0.6731(13) -0.2598(11) 0.4391(10) 0.055(3) Uani 1 1 d . . . H3A H -0.7710 -0.2987 0.4194 0.066 Uiso 1 1 calc R . . C4 C -0.6234(12) -0.1822(11) 0.3719(10) 0.051(3) Uani 1 1 d . . . H4A H -0.6860 -0.1672 0.3071 0.061 Uiso 1 1 calc R . . C5 C -0.4782(11) -0.1255(10) 0.4008(9) 0.040(2) Uani 1 1 d . . . C6 C -0.3890(12) -0.1524(11) 0.4956(9) 0.047(3) Uani 1 1 d . . . H6A H -0.2902 -0.1192 0.5144 0.056 Uiso 1 1 calc R . . C7 C -0.4470(13) -0.2279(10) 0.5609(10) 0.051(3) Uani 1 1 d . . . H7A H -0.3875 -0.2423 0.6278 0.061 Uiso 1 1 calc R . . C8 C -0.4266(10) -0.0409(9) 0.3266(8) 0.034(2) Uani 1 1 d . . . C9 C -0.4284(10) 0.0726(9) 0.2046(8) 0.032(2) Uani 1 1 d . . . C10 C -0.4859(10) 0.1312(9) 0.1071(9) 0.037(2) Uani 1 1 d . . . C11 C -0.6291(13) 0.1123(10) 0.0681(10) 0.048(3) Uani 1 1 d . . . H11A H -0.6897 0.0626 0.1019 0.057 Uiso 1 1 calc R . . C12 C -0.6827(14) 0.1682(11) -0.0225(11) 0.057(3) Uani 1 1 d . . . H12A H -0.7801 0.1602 -0.0479 0.069 Uiso 1 1 calc R . . C13 C -0.4574(11) 0.2513(10) -0.0355(10) 0.047(3) Uani 1 1 d . . . H13A H -0.3980 0.2993 -0.0712 0.057 Uiso 1 1 calc R . . C14 C -0.4003(11) 0.2025(11) 0.0527(10) 0.048(3) Uani 1 1 d . . . H14A H -0.3019 0.2160 0.0784 0.057 Uiso 1 1 calc R . . C15 C -0.6564(17) 0.2941(12) -0.1697(11) 0.073(4) Uani 1 1 d . . . H15A H -0.5936 0.3069 -0.2173 0.087 Uiso 1 1 calc R . . H15B H -0.7478 0.2355 -0.2175 0.087 Uiso 1 1 calc R . . C16 C -0.6770(14) 0.4157(13) -0.1326(10) 0.063(4) Uani 1 1 d . . . H16A H -0.7161 0.4496 -0.1992 0.095 Uiso 1 1 calc R . . H16B H -0.5868 0.4749 -0.0863 0.095 Uiso 1 1 calc R . . H16C H -0.7418 0.4036 -0.0877 0.095 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 0.0605(11) 0.0548(10) 0.1354(17) 0.0474(11) 0.0484(11) 0.0213(8) Cu2 0.0753(12) 0.0551(10) 0.0839(12) 0.0306(9) 0.0093(10) 0.0262(9) Cu3 0.0356(8) 0.0490(8) 0.1010(13) 0.0255(8) 0.0322(8) 0.0114(7) Cu4 0.0342(8) 0.0508(8) 0.0706(10) 0.0113(7) -0.0117(7) 0.0182(7) I1 0.0493(4) 0.0392(4) 0.0405(4) 0.0118(3) 0.0084(3) 0.0139(3) I2 0.0368(4) 0.0709(6) 0.0660(5) 0.0278(4) 0.0148(4) 0.0137(4) I3 0.0450(4) 0.0403(4) 0.0519(4) 0.0178(3) 0.0233(3) 0.0178(3) I4 0.0445(4) 0.0396(4) 0.0625(5) 0.0159(4) 0.0209(4) 0.0183(3) I5 0.0433(4) 0.0373(4) 0.0590(5) 0.0074(3) 0.0001(3) 0.0145(3) N1 0.030(5) 0.053(5) 0.035(5) 0.012(4) 0.010(4) 0.015(4) N2 0.018(3) 0.035(4) 0.053(4) -0.005(3) -0.005(3) 0.011(3) N3 0.018(3) 0.035(4) 0.053(4) -0.005(3) -0.005(3) 0.011(3) N4 0.051(6) 0.050(5) 0.047(5) 0.017(4) 0.028(5) 0.020(5) N5 0.062(7) 0.039(5) 0.039(5) 0.014(4) 0.005(4) 0.015(5) C1 0.081(11) 0.061(8) 0.069(9) 0.026(7) 0.027(8) -0.007(7) C2 0.097(11) 0.062(8) 0.067(9) 0.035(7) 0.058(8) 0.030(8) C3 0.045(7) 0.061(8) 0.062(8) 0.019(6) 0.019(6) 0.013(6) C4 0.041(7) 0.056(7) 0.049(7) 0.025(6) 0.004(5) 0.007(5) C5 0.034(6) 0.039(6) 0.048(6) 0.015(5) 0.008(5) 0.019(5) C6 0.032(6) 0.059(7) 0.055(7) 0.028(6) 0.014(5) 0.014(5) C7 0.061(8) 0.047(7) 0.047(7) 0.020(5) 0.013(6) 0.019(6) C8 0.024(5) 0.036(5) 0.039(5) 0.007(4) 0.008(4) 0.004(4) C9 0.029(5) 0.030(5) 0.036(5) 0.012(4) 0.009(4) 0.006(4) C10 0.026(5) 0.038(5) 0.047(6) 0.007(5) 0.006(4) 0.012(4) C11 0.053(7) 0.041(6) 0.060(7) 0.033(6) 0.022(6) 0.018(5) C12 0.049(7) 0.051(7) 0.073(9) 0.020(6) 0.014(6) 0.020(6) C13 0.036(6) 0.047(6) 0.065(8) 0.022(6) 0.023(6) 0.008(5) C14 0.030(6) 0.056(7) 0.064(7) 0.032(6) 0.017(5) 0.013(5) C15 0.091(11) 0.056(8) 0.056(8) 0.025(7) -0.016(7) 0.033(8) C16 0.064(9) 0.094(10) 0.053(7) 0.029(7) 0.018(6) 0.053(8) _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 Cu2 2.539(3) 2_565 ? Cu1 I4 2.565(3) 2_565 ? Cu1 Cu3 2.617(3) 2_565 ? Cu1 I2 2.617(2) 2_565 ? Cu1 I3 2.824(2) 2_565 ? Cu1 I1 2.885(3) . ? Cu2 Cu1 2.539(3) 2_565 ? Cu2 I1 2.573(3) . ? Cu2 Cu2 2.710(4) 2_565 ? Cu2 I2 2.727(3) . ? Cu2 I1 2.750(3) 2_565 ? Cu2 I3 2.818(3) . ? Cu3 N2 2.122(8) . ? Cu3 I3 2.567(3) . ? Cu3 I4 2.590(2) . ? Cu3 Cu1 2.617(3) 2_565 ? Cu3 Cu4 3.054(3) . ? Cu4 N3 2.044(8) . ? Cu4 Cu4 2.536(3) 2_556 ? Cu4 I5 2.566(2) 2_556 ? Cu4 I5 2.599(2) . ? I1 Cu2 2.750(3) 2_565 ? I2 Cu1 2.617(2) 2_565 ? I3 Cu1 2.824(2) 2_565 ? I4 Cu1 2.565(3) 2_565 ? I5 Cu4 2.566(2) 2_556 ? N1 C8 1.337(12) . ? N1 C9 1.357(12) . ? N2 N3 1.194(12) . ? N2 C9 1.313(12) . ? N3 C8 1.322(12) . ? N4 C3 1.341(15) . ? N4 C7 1.358(15) . ? N4 C2 1.497(13) . ? N5 C13 1.339(14) . ? N5 C12 1.369(15) . ? N5 C15 1.495(13) . ? C1 C2 1.457(17) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.375(15) . ? C3 H3A 0.9500 . ? C4 C5 1.406(15) . ? C4 H4A 0.9500 . ? C5 C6 1.403(14) . ? C5 C8 1.499(14) . ? C6 C7 1.380(15) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C9 C10 1.496(13) . ? C10 C11 1.384(15) . ? C10 C14 1.405(14) . ? C11 C12 1.401(15) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C14 1.341(15) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.469(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 Cu2 Cu1 I4 171.58(10) 2_565 2_565 ? Cu2 Cu1 Cu3 114.47(9) 2_565 2_565 ? I4 Cu1 Cu3 59.98(5) 2_565 2_565 ? Cu2 Cu1 I2 63.82(7) 2_565 2_565 ? I4 Cu1 I2 124.52(8) 2_565 2_565 ? Cu3 Cu1 I2 143.89(10) 2_565 2_565 ? Cu2 Cu1 I3 63.14(8) 2_565 2_565 ? I4 Cu1 I3 113.83(8) 2_565 2_565 ? Cu3 Cu1 I3 56.14(7) 2_565 2_565 ? I2 Cu1 I3 99.01(9) 2_565 2_565 ? Cu2 Cu1 I1 60.52(6) 2_565 . ? I4 Cu1 I1 113.85(8) 2_565 . ? Cu3 Cu1 I1 107.45(9) 2_565 . ? I2 Cu1 I1 102.10(7) 2_565 . ? I3 Cu1 I1 99.90(8) 2_565 . ? Cu1 Cu2 I1 175.11(10) 2_565 . ? Cu1 Cu2 Cu2 122.21(12) 2_565 2_565 ? I1 Cu2 Cu2 62.68(6) . 2_565 ? Cu1 Cu2 I2 59.48(6) 2_565 . ? I1 Cu2 I2 117.68(8) . . ? Cu2 Cu2 I2 131.87(12) 2_565 . ? Cu1 Cu2 I1 65.98(9) 2_565 2_565 ? I1 Cu2 I1 118.90(8) . 2_565 ? Cu2 Cu2 I1 56.23(8) 2_565 2_565 ? I2 Cu2 I1 102.89(7) . 2_565 ? Cu1 Cu2 I3 63.38(6) 2_565 . ? I1 Cu2 I3 114.16(7) . . ? Cu2 Cu2 I3 128.62(13) 2_565 . ? I2 Cu2 I3 96.59(7) . . ? I1 Cu2 I3 103.42(8) 2_565 . ? N2 Cu3 I3 123.9(2) . . ? N2 Cu3 I4 112.9(2) . . ? I3 Cu3 I4 122.30(7) . . ? N2 Cu3 Cu1 151.6(3) . 2_565 ? I3 Cu3 Cu1 66.02(6) . 2_565 ? I4 Cu3 Cu1 59.00(7) . 2_565 ? N2 Cu3 Cu4 62.8(2) . . ? I3 Cu3 Cu4 139.91(8) . . ? I4 Cu3 Cu4 74.69(7) . . ? Cu1 Cu3 Cu4 129.78(8) 2_565 . ? N3 Cu4 Cu4 158.7(3) . 2_556 ? N3 Cu4 I5 128.6(2) . 2_556 ? Cu4 Cu4 I5 61.25(6) 2_556 2_556 ? N3 Cu4 I5 107.1(2) . . ? Cu4 Cu4 I5 59.94(7) 2_556 . ? I5 Cu4 I5 121.19(7) 2_556 . ? N3 Cu4 Cu3 64.0(3) . . ? Cu4 Cu4 Cu3 122.34(10) 2_556 . ? I5 Cu4 Cu3 141.67(8) 2_556 . ? I5 Cu4 Cu3 75.37(8) . . ? Cu2 I1 Cu2 61.10(8) . 2_565 ? Cu2 I1 Cu1 114.59(6) . . ? Cu2 I1 Cu1 53.49(6) 2_565 . ? Cu1 I2 Cu2 56.69(8) 2_565 . ? Cu3 I3 Cu2 107.16(6) . . ? Cu3 I3 Cu1 57.85(6) . 2_565 ? Cu2 I3 Cu1 53.49(6) . 2_565 ? Cu1 I4 Cu3 61.01(6) 2_565 . ? Cu4 I5 Cu4 58.81(7) 2_556 . ? C8 N1 C9 101.4(8) . . ? N3 N2 C9 113.1(9) . . ? N3 N2 Cu3 114.4(6) . . ? C9 N2 Cu3 132.0(7) . . ? N2 N3 C8 106.3(8) . . ? N2 N3 Cu4 118.1(7) . . ? C8 N3 Cu4 135.6(8) . . ? C3 N4 C7 120.0(10) . . ? C3 N4 C2 119.6(11) . . ? C7 N4 C2 120.4(10) . . ? C13 N5 C12 120.1(9) . . ? C13 N5 C15 120.9(11) . . ? C12 N5 C15 118.8(11) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C1 C2 N4 111.9(10) . . ? C1 C2 H2A 109.2 . . ? N4 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? N4 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? N4 C3 C4 122.0(11) . . ? N4 C3 H3A 119.0 . . ? C4 C3 H3A 119.0 . . ? C3 C4 C5 118.8(11) . . ? C3 C4 H4A 120.6 . . ? C5 C4 H4A 120.6 . . ? C6 C5 C4 118.8(10) . . ? C6 C5 C8 123.3(9) . . ? C4 C5 C8 117.8(9) . . ? C7 C6 C5 118.9(11) . . ? C7 C6 H6A 120.5 . . ? C5 C6 H6A 120.5 . . ? N4 C7 C6 121.3(11) . . ? N4 C7 H7A 119.4 . . ? C6 C7 H7A 119.4 . . ? N3 C8 N1 111.6(9) . . ? N3 C8 C5 128.0(9) . . ? N1 C8 C5 120.5(8) . . ? N2 C9 N1 107.5(8) . . ? N2 C9 C10 132.4(9) . . ? N1 C9 C10 120.1(9) . . ? C11 C10 C14 119.0(9) . . ? C11 C10 C9 118.5(9) . . ? C14 C10 C9 122.5(9) . . ? C10 C11 C12 118.5(10) . . ? C10 C11 H11A 120.8 . . ? C12 C11 H11A 120.8 . . ? N5 C12 C11 120.4(12) . . ? N5 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? N5 C13 C14 121.8(10) . . ? N5 C13 H13A 119.1 . . ? C14 C13 H13A 119.1 . . ? C13 C14 C10 120.2(10) . . ? C13 C14 H14A 119.9 . . ? C10 C14 H14A 119.9 . . ? C16 C15 N5 114.0(11) . . ? C16 C15 H15A 108.8 . . ? N5 C15 H15A 108.8 . . ? C16 C15 H15B 108.8 . . ? N5 C15 H15B 108.8 . . ? H15A C15 H15B 107.7 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 2.309 _refine_diff_density_min -1.564 _refine_diff_density_rms 0.228 #=================================END data_2 _database_code_depnum_ccdc_archive 'CCDC 853330' #TrackingRef '1-2-revised-new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H24 Br3 Cu6 N15' _chemical_formula_weight 1287.67 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' _cell_length_a 31.754(12) _cell_length_b 10.712(4) _cell_length_c 21.206(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 7213(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4992 _exptl_absorpt_coefficient_mu 6.855 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7469 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _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 ? _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 13795 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3271 _reflns_number_gt 2909 _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^)+(0.0993P)^2^+215.4288P] 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 H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.12(4) _refine_ls_number_reflns 3271 _refine_ls_number_parameters 232 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0633 _refine_ls_wR_factor_ref 0.1831 _refine_ls_wR_factor_gt 0.1752 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.19640(4) -0.26073(15) 0.70754(8) 0.0364(4) Uani 1 1 d . . . Cu2 Cu 0.22165(5) -0.49202(16) 0.82317(8) 0.0436(4) Uani 1 1 d . . . Cu3 Cu 0.11724(4) -0.47999(14) 0.82668(8) 0.0343(4) Uani 1 1 d . . . Br1 Br 0.2500 -0.2500 0.79723(10) 0.0403(5) Uani 1 2 d S . . Br2 Br 0.16855(4) -0.49163(12) 0.73515(8) 0.0450(4) Uani 1 1 d . . . N3 N 0.1907(3) -0.4850(8) 0.9019(5) 0.0282(6) Uani 1 1 d . . . N2 N 0.1480(3) -0.5185(9) 0.9011(5) 0.0282(6) Uani 1 1 d . . . N1 N 0.1684(2) -0.4993(8) 1.0015(6) 0.0282(6) Uani 1 1 d . . . N4 N 0.3166(2) -0.3389(8) 1.0400(5) 0.0282(6) Uani 1 1 d . . . N5 N 0.0201(2) -0.6695(9) 1.0336(5) 0.0282(6) Uani 1 1 d . . . N7 N 0.0221(2) -0.0160(9) 0.8791(5) 0.0282(6) Uani 1 1 d . . . N8 N 0.0000 0.0000 0.7765(8) 0.0282(6) Uani 1 2 d S . . N6 N 0.1467(3) -0.1688(9) 0.7434(5) 0.0282(6) Uani 1 1 d . . . C5 C 0.3106(3) -0.3422(13) 0.9769(7) 0.040(3) Uani 1 1 d . . . H2 H 0.3317 -0.3100 0.9495 0.048 Uiso 1 1 calc R . . C4 C 0.2737(3) -0.3926(12) 0.9517(6) 0.038(3) Uani 1 1 d . . . H13 H 0.2709 -0.3966 0.9071 0.045 Uiso 1 1 calc R . . C3 C 0.2416(3) -0.4361(10) 0.9882(6) 0.029(2) Uani 1 1 d . . . C2 C 0.2480(3) -0.4349(11) 1.0526(7) 0.034(3) Uani 1 1 d . . . H5 H 0.2267 -0.4650 1.0802 0.041 Uiso 1 1 calc R . . C1 C 0.2861(3) -0.3888(10) 1.0771(7) 0.036(3) Uani 1 1 d . . . H18 H 0.2907 -0.3928 1.1213 0.043 Uiso 1 1 calc R . . C6 C 0.2006(3) -0.4731(10) 0.9641(6) 0.026(2) Uani 1 1 d . . . C7 C 0.1370(3) -0.5255(10) 0.9618(6) 0.024(2) Uani 1 1 d . . . C8 C 0.0953(3) -0.5692(10) 0.9837(6) 0.029(2) Uani 1 1 d . . . C9 C 0.0834(4) -0.5466(11) 1.0463(7) 0.038(3) Uani 1 1 d . . . H14 H 0.1006 -0.4972 1.0732 0.046 Uiso 1 1 calc R . . C10 C 0.0457(4) -0.5983(13) 1.0686(7) 0.043(3) Uani 1 1 d . . . H12 H 0.0378 -0.5818 1.1110 0.052 Uiso 1 1 calc R . . C11 C 0.0311(4) -0.6863(12) 0.9735(6) 0.036(3) Uani 1 1 d . . . H17 H 0.0133 -0.7357 0.9476 0.043 Uiso 1 1 calc R . . C12 C 0.0674(4) -0.6353(13) 0.9464(6) 0.040(3) Uani 1 1 d . . . H15 H 0.0729 -0.6460 0.9027 0.048 Uiso 1 1 calc R . . C13 C 0.1417(3) -0.1629(11) 0.8054(6) 0.034(3) Uani 1 1 d . . . H1 H 0.1635 -0.1938 0.8317 0.041 Uiso 1 1 calc R . . C14 C 0.1055(3) -0.1130(11) 0.8338(7) 0.036(3) Uani 1 1 d . . . H16 H 0.1031 -0.1094 0.8784 0.043 Uiso 1 1 calc R . . C15 C 0.0729(3) -0.0681(9) 0.7949(6) 0.022(2) Uani 1 1 d . . . C18 C 0.0319(3) -0.0242(9) 0.8190(6) 0.022(2) Uani 1 1 d . . . C16 C 0.0809(4) -0.0669(13) 0.7302(6) 0.036(3) Uani 1 1 d . . . H7 H 0.0616 -0.0280 0.7021 0.043 Uiso 1 1 calc R . . C17 C 0.1163(3) -0.1218(11) 0.7077(6) 0.032(2) Uani 1 1 d . . . H11 H 0.1196 -0.1268 0.6632 0.038 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 0.0193(6) 0.0593(10) 0.0305(9) -0.0092(7) 0.0056(6) 0.0003(6) Cu2 0.0219(6) 0.0763(11) 0.0328(10) -0.0081(9) 0.0044(7) 0.0017(6) Cu3 0.0238(6) 0.0456(7) 0.0336(9) 0.0079(7) -0.0091(6) 0.0008(5) Br1 0.0313(9) 0.0521(11) 0.0374(12) 0.000 0.000 -0.0007(6) Br2 0.0354(7) 0.0542(8) 0.0453(10) 0.0037(6) 0.0000(6) -0.0006(5) N3 0.0161(12) 0.0390(15) 0.0294(17) 0.0021(15) 0.0004(14) -0.0009(14) N2 0.0161(12) 0.0390(15) 0.0294(17) 0.0021(15) 0.0004(14) -0.0009(14) N1 0.0161(12) 0.0390(15) 0.0294(17) 0.0021(15) 0.0004(14) -0.0009(14) N4 0.0161(12) 0.0390(15) 0.0294(17) 0.0021(15) 0.0004(14) -0.0009(14) N5 0.0161(12) 0.0390(15) 0.0294(17) 0.0021(15) 0.0004(14) -0.0009(14) N7 0.0161(12) 0.0390(15) 0.0294(17) 0.0021(15) 0.0004(14) -0.0009(14) N8 0.0161(12) 0.0390(15) 0.0294(17) 0.0021(15) 0.0004(14) -0.0009(14) N6 0.0161(12) 0.0390(15) 0.0294(17) 0.0021(15) 0.0004(14) -0.0009(14) C5 0.016(4) 0.064(8) 0.040(8) -0.001(6) 0.008(5) -0.003(5) C4 0.026(5) 0.058(7) 0.029(7) 0.006(6) 0.001(5) -0.009(5) C3 0.016(4) 0.028(5) 0.041(7) 0.003(5) -0.011(5) 0.002(4) C2 0.018(4) 0.041(6) 0.042(8) 0.001(6) 0.002(5) -0.007(4) C1 0.031(5) 0.042(6) 0.035(7) 0.013(5) -0.009(5) -0.009(5) C6 0.025(5) 0.035(5) 0.019(6) 0.007(4) 0.001(4) -0.005(4) C7 0.016(4) 0.031(4) 0.026(6) 0.007(4) -0.010(4) 0.001(4) C8 0.030(5) 0.037(5) 0.018(5) 0.004(4) 0.002(5) -0.004(4) C9 0.033(6) 0.041(6) 0.040(7) -0.001(5) 0.002(5) -0.016(5) C10 0.033(5) 0.065(8) 0.032(7) 0.001(6) 0.011(6) -0.009(5) C11 0.029(5) 0.055(7) 0.023(6) -0.006(5) -0.008(5) -0.007(5) C12 0.033(5) 0.069(8) 0.018(6) -0.008(6) 0.001(5) -0.013(6) C13 0.023(5) 0.050(6) 0.030(7) 0.000(5) 0.005(5) 0.013(4) C14 0.023(5) 0.053(6) 0.031(7) 0.003(5) 0.006(5) 0.013(4) C15 0.019(4) 0.025(4) 0.024(6) 0.005(4) 0.005(4) 0.002(3) C18 0.015(4) 0.027(4) 0.026(6) -0.003(4) 0.001(4) 0.007(4) C16 0.035(6) 0.056(7) 0.016(6) -0.001(5) 0.001(5) 0.003(5) C17 0.027(5) 0.051(7) 0.018(6) -0.002(5) 0.007(4) 0.014(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N7 1.942(11) 7_544 ? Cu1 N6 2.010(9) . ? Cu1 Br1 2.555(2) . ? Cu1 Br2 2.691(2) . ? Cu2 N3 1.938(11) . ? Cu2 N5 1.992(9) 8_534 ? Cu2 Br2 2.515(2) . ? Cu2 Br1 2.799(2) . ? Cu3 N2 1.902(10) . ? Cu3 N4 1.933(9) 12_444 ? Cu3 Br2 2.537(2) . ? Br1 Cu1 2.555(2) 14_545 ? Br1 Cu2 2.799(2) 14_545 ? N3 C6 1.363(16) . ? N3 N2 1.404(12) . ? N2 C7 1.335(15) . ? N1 C6 1.324(14) . ? N1 C7 1.336(14) . ? N4 C5 1.352(16) . ? N4 C1 1.357(15) . ? N4 Cu3 1.933(9) 4_545 ? N5 C11 1.333(15) . ? N5 C10 1.339(16) . ? N5 Cu2 1.992(9) 16_435 ? N7 C18 1.315(16) . ? N7 N7 1.445(16) 2 ? N7 Cu1 1.942(11) 3 ? N8 C18 1.382(15) . ? N8 C18 1.382(15) 2 ? N6 C13 1.325(16) . ? N6 C17 1.327(14) . ? C5 C4 1.398(16) . ? C5 H2 0.9500 . ? C4 C3 1.363(16) . ? C4 H13 0.9500 . ? C3 C2 1.382(19) . ? C3 C6 1.452(14) . ? C2 C1 1.407(14) . ? C2 H5 0.9500 . ? C1 H18 0.9500 . ? C7 C8 1.481(14) . ? C8 C12 1.382(16) . ? C8 C9 1.401(17) . ? C9 C10 1.403(15) . ? C9 H14 0.9500 . ? C10 H12 0.9500 . ? C11 C12 1.401(16) . ? C11 H17 0.9500 . ? C12 H15 0.9500 . ? C13 C14 1.401(14) . ? C13 H1 0.9500 . ? C14 C15 1.409(15) . ? C14 H16 0.9500 . ? C15 C16 1.397(16) . ? C15 C18 1.473(13) . ? C16 C17 1.356(15) . ? C16 H7 0.9500 . ? C17 H11 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N7 Cu1 N6 138.0(4) 7_544 . ? N7 Cu1 Br1 107.2(3) 7_544 . ? N6 Cu1 Br1 102.7(3) . . ? N7 Cu1 Br2 109.2(3) 7_544 . ? N6 Cu1 Br2 96.3(3) . . ? Br1 Cu1 Br2 95.64(7) . . ? N3 Cu2 N5 140.6(4) . 8_534 ? N3 Cu2 Br2 107.4(3) . . ? N5 Cu2 Br2 101.9(3) 8_534 . ? N3 Cu2 Br1 107.2(3) . . ? N5 Cu2 Br1 96.3(3) 8_534 . ? Br2 Cu2 Br1 93.91(7) . . ? N2 Cu3 N4 147.6(4) . 12_444 ? N2 Cu3 Br2 107.1(3) . . ? N4 Cu3 Br2 104.2(3) 12_444 . ? Cu1 Br1 Cu1 83.78(10) . 14_545 ? Cu1 Br1 Cu2 113.72(6) . 14_545 ? Cu1 Br1 Cu2 83.71(6) 14_545 14_545 ? Cu1 Br1 Cu2 83.71(6) . . ? Cu1 Br1 Cu2 113.72(6) 14_545 . ? Cu2 Br1 Cu2 157.33(11) 14_545 . ? Cu2 Br2 Cu3 82.12(8) . . ? Cu2 Br2 Cu1 86.72(7) . . ? Cu3 Br2 Cu1 109.41(7) . . ? C6 N3 N2 104.9(9) . . ? C6 N3 Cu2 136.1(8) . . ? N2 N3 Cu2 118.1(8) . . ? C7 N2 N3 104.8(9) . . ? C7 N2 Cu3 132.7(7) . . ? N3 N2 Cu3 116.7(7) . . ? C6 N1 C7 104.1(11) . . ? C5 N4 C1 117.6(10) . . ? C5 N4 Cu3 121.6(7) . 4_545 ? C1 N4 Cu3 120.7(9) . 4_545 ? C11 N5 C10 116.6(10) . . ? C11 N5 Cu2 122.8(8) . 16_435 ? C10 N5 Cu2 120.3(9) . 16_435 ? C18 N7 N7 104.3(5) . 2 ? C18 N7 Cu1 135.2(7) . 3 ? N7 N7 Cu1 119.6(3) 2 3 ? C18 N8 C18 98.5(14) . 2 ? C13 N6 C17 117.4(9) . . ? C13 N6 Cu1 119.6(7) . . ? C17 N6 Cu1 122.8(8) . . ? N4 C5 C4 120.4(11) . . ? N4 C5 H2 119.8 . . ? C4 C5 H2 119.8 . . ? C3 C4 C5 122.9(13) . . ? C3 C4 H13 118.5 . . ? C5 C4 H13 118.5 . . ? C4 C3 C2 116.6(10) . . ? C4 C3 C6 124.4(12) . . ? C2 C3 C6 118.8(10) . . ? C3 C2 C1 119.7(11) . . ? C3 C2 H5 120.1 . . ? C1 C2 H5 120.1 . . ? N4 C1 C2 122.5(12) . . ? N4 C1 H18 118.7 . . ? C2 C1 H18 118.7 . . ? N1 C6 N3 112.5(10) . . ? N1 C6 C3 122.6(11) . . ? N3 C6 C3 124.9(10) . . ? N2 C7 N1 113.7(9) . . ? N2 C7 C8 123.6(9) . . ? N1 C7 C8 122.5(11) . . ? C12 C8 C9 117.4(10) . . ? C12 C8 C7 123.7(11) . . ? C9 C8 C7 118.9(10) . . ? C8 C9 C10 118.7(11) . . ? C8 C9 H14 120.6 . . ? C10 C9 H14 120.6 . . ? N5 C10 C9 123.8(13) . . ? N5 C10 H12 118.1 . . ? C9 C10 H12 118.1 . . ? N5 C11 C12 123.8(11) . . ? N5 C11 H17 118.1 . . ? C12 C11 H17 118.1 . . ? C8 C12 C11 119.4(11) . . ? C8 C12 H15 120.3 . . ? C11 C12 H15 120.3 . . ? N6 C13 C14 122.9(11) . . ? N6 C13 H1 118.6 . . ? C14 C13 H1 118.6 . . ? C13 C14 C15 118.8(12) . . ? C13 C14 H16 120.6 . . ? C15 C14 H16 120.6 . . ? C16 C15 C14 116.3(10) . . ? C16 C15 C18 119.9(10) . . ? C14 C15 C18 123.8(11) . . ? N7 C18 N8 116.4(9) . . ? N7 C18 C15 124.5(10) . . ? N8 C18 C15 118.8(11) . . ? C17 C16 C15 119.5(11) . . ? C17 C16 H7 120.2 . . ? C15 C16 H7 120.2 . . ? N6 C17 C16 124.6(12) . . ? N6 C17 H11 117.7 . . ? C16 C17 H11 117.7 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.267 _refine_diff_density_min -1.798 _refine_diff_density_rms 0.184