Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Md. Badruz Zaman' 'Konstantin Udachin' 'Md. Akhtaruzzaman' 'Yoshiro Yamashitab' 'John A. Ripmeester' _publ_contact_author_name 'Prof John Ripmeester' _publ_contact_author_address ; National Res Council Canada Steacie Inst Mol Sci, 100 Sussex Dr Ottawa ON K1A 0R6 CANADA ; _publ_contact_author_email '?' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Organic/Inorganic Supramolecular Channel Frameworks Containing Photosensitive Azobenzene as an Included Guest ; data_zam28 _database_code_CSD 181463 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cu(NO3)2(C14H10N2)(H2O)2*0.5(C12H10N2)' _chemical_melting_point ? _chemical_formula_moiety 'C14H12CuN4O8, C12H10N2' _chemical_formula_sum 'C20 H17 Cu N5 O8' _chemical_formula_weight 518.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 15.6870(10) _cell_length_b 7.8420(10) _cell_length_c 17.2560(10) _cell_angle_alpha 90.000(10) _cell_angle_beta 90.410(10) _cell_angle_gamma 90.000(10) _cell_volume 2122.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.624 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1060 _exptl_absorpt_coefficient_mu 1.089 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _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 24521 _diffrn_reflns_av_R_equivalents 0.0649 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 28.74 _reflns_number_total 5509 _reflns_number_gt 4177 _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^)+(0.0537P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5509 _refine_ls_number_parameters 357 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 0.979 _refine_ls_restrained_S_all 0.979 _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 0.0000 0.5000 0.5000 0.01811(9) Uani 1 2 d S . . Cu2 Cu -0.2500 0.90643(4) 0.7500 0.01913(9) Uani 1 2 d S . . O1 O -0.31096(10) 1.08455(17) 0.68869(8) 0.0239(3) Uani 1 1 d . . . H12 H -0.2837(18) 1.157(4) 0.6709(15) 0.057(9) Uiso 1 1 d . . . H11 H -0.3464(16) 1.121(3) 0.7179(14) 0.041(7) Uiso 1 1 d . . . O2 O -0.04959(10) 0.30054(17) 0.44172(8) 0.0231(3) Uani 1 1 d . . . H22 H -0.0211(15) 0.222(3) 0.4314(13) 0.032(7) Uiso 1 1 d . . . H21 H -0.0899(16) 0.274(3) 0.4683(14) 0.040(7) Uiso 1 1 d . . . O3 O -0.22096(9) 0.36611(18) 0.64953(8) 0.0305(3) Uani 1 1 d . . . O4 O -0.11141(9) 0.47396(16) 0.59191(8) 0.0257(3) Uani 1 1 d . . . O5 O -0.17557(9) 0.25070(19) 0.54371(8) 0.0337(3) Uani 1 1 d . . . O6 O -0.02058(9) 1.00358(17) 0.60266(9) 0.0331(3) Uani 1 1 d . . . O7 O -0.13552(9) 0.91069(17) 0.65776(8) 0.0285(3) Uani 1 1 d . . . O8 O -0.07150(9) 1.13806(18) 0.70108(8) 0.0309(3) Uani 1 1 d . . . N1 N 0.07771(9) 0.34917(19) 0.56121(8) 0.0189(3) Uani 1 1 d . . . N2 N -0.31493(9) 0.73189(18) 0.68876(8) 0.0191(3) Uani 1 1 d . . . N3 N -0.16966(10) 0.3637(2) 0.59500(9) 0.0227(3) Uani 1 1 d . . . N5 N -0.07597(10) 1.01725(19) 0.65383(9) 0.0222(3) Uani 1 1 d . . . C1 C 0.12951(11) 0.2561(2) 0.68486(10) 0.0213(4) Uani 1 1 d . . . C2 C 0.17731(12) 0.1283(2) 0.64919(11) 0.0241(4) Uani 1 1 d . . . H2 H 0.2110(13) 0.052(3) 0.6784(11) 0.021(5) Uiso 1 1 d . . . C3 C 0.17485(12) 0.1158(2) 0.56926(11) 0.0232(4) Uani 1 1 d . . . H3 H 0.2013(13) 0.035(3) 0.5470(12) 0.023(5) Uiso 1 1 d . . . C4 C 0.12535(12) 0.2284(2) 0.52724(10) 0.0217(4) Uani 1 1 d . . . H4 H 0.1231(12) 0.224(2) 0.4709(11) 0.022(5) Uiso 1 1 d . . . C5 C 0.08019(11) 0.3628(2) 0.63853(10) 0.0206(4) Uani 1 1 d . . . H6 H 0.0464(14) 0.444(3) 0.6615(13) 0.033(6) Uiso 1 1 d . . . C6 C 0.12963(12) 0.2796(2) 0.76724(11) 0.0247(4) Uani 1 1 d . . . C7 C 0.12926(12) 0.3024(2) 0.83589(11) 0.0257(4) Uani 1 1 d . . . C8 C -0.37005(12) 0.6737(2) 0.41488(11) 0.0260(4) Uani 1 1 d . . . C9 C -0.36897(12) 0.6526(2) 0.48373(11) 0.0250(4) Uani 1 1 d . . . C10 C -0.36706(11) 0.6318(2) 0.56601(10) 0.0223(4) Uani 1 1 d . . . C11 C -0.31856(12) 0.7427(2) 0.61125(10) 0.0212(4) Uani 1 1 d . . . H11' H -0.2878(12) 0.827(3) 0.5891(11) 0.019(5) Uiso 1 1 d . . . C12 C -0.36034(12) 0.6095(2) 0.72373(11) 0.0218(4) Uani 1 1 d . . . H12' H -0.3593(13) 0.609(3) 0.7781(12) 0.027(6) Uiso 1 1 d . . . C13 C -0.41057(12) 0.4954(2) 0.68324(12) 0.0241(4) Uani 1 1 d . . . H13 H -0.4409(13) 0.416(3) 0.7073(12) 0.028(6) Uiso 1 1 d . . . C14 C -0.41425(12) 0.5050(2) 0.60302(12) 0.0251(4) Uani 1 1 d . . . H14 H -0.4477(13) 0.423(3) 0.5725(12) 0.024(5) Uiso 1 1 d . . . N1A N -0.46707(13) 1.0414(3) 0.50428(16) 0.0567(7) Uani 1 1 d . . . C1A C -0.43302(17) 1.1059(3) 0.43317(18) 0.0517(7) Uani 1 1 d . . . C2A C -0.35611(17) 0.1940(3) 0.43962(18) 0.0555(8) Uani 1 1 d . . . H2A H -0.3299 0.2066 0.4891 0.067 Uiso 1 1 calc R . . C3A C -0.31795(18) 0.2621(4) 0.3762(2) 0.0617(8) Uani 1 1 d . . . H3A H -0.2651 0.3202 0.3815 0.074 Uiso 1 1 calc R . . C4A C 0.14401(18) 0.7531(4) 0.80371(19) 0.0624(8) Uani 1 1 d . . . H4A H 0.1703 0.7051 0.7593 0.075 Uiso 1 1 calc R . . C5A C 0.06662(18) -0.1602(4) 0.79679(18) 0.0597(8) Uani 1 1 d . . . H5A H 0.0401 -0.1504 0.7473 0.072 Uiso 1 1 calc R . . C6A C 0.02867(18) -0.0896(4) 0.85955(19) 0.0591(8) Uani 1 1 d . . . H6A H -0.0236 -0.0294 0.8538 0.071 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 0.02118(16) 0.01997(15) 0.01317(16) -0.00007(11) -0.00076(12) 0.00045(11) Cu2 0.02256(16) 0.02109(16) 0.01373(15) 0.000 -0.00134(12) 0.000 O1 0.0260(7) 0.0235(7) 0.0222(7) 0.0046(6) 0.0012(6) -0.0004(6) O2 0.0256(7) 0.0219(7) 0.0219(7) -0.0038(5) 0.0008(6) 0.0005(6) O3 0.0288(7) 0.0304(7) 0.0325(8) -0.0027(6) 0.0155(6) -0.0040(6) O4 0.0291(7) 0.0255(7) 0.0228(7) -0.0008(5) 0.0067(6) -0.0069(6) O5 0.0318(8) 0.0370(8) 0.0324(8) -0.0139(6) 0.0055(6) -0.0078(6) O6 0.0297(8) 0.0323(8) 0.0375(9) -0.0087(6) 0.0155(7) -0.0031(6) O7 0.0317(7) 0.0290(7) 0.0248(7) -0.0042(6) 0.0091(6) -0.0099(6) O8 0.0307(7) 0.0298(7) 0.0322(8) -0.0137(6) 0.0077(6) -0.0059(6) N1 0.0203(7) 0.0223(7) 0.0140(7) 0.0008(6) 0.0003(6) 0.0005(6) N2 0.0207(7) 0.0227(7) 0.0140(7) 0.0001(6) 0.0004(6) -0.0010(6) N3 0.0217(8) 0.0249(8) 0.0216(8) 0.0017(6) 0.0020(6) 0.0010(6) N5 0.0199(7) 0.0236(8) 0.0233(8) -0.0009(6) 0.0034(6) 0.0016(6) C1 0.0213(8) 0.0258(9) 0.0166(9) 0.0005(7) -0.0007(7) -0.0013(7) C2 0.0227(9) 0.0264(9) 0.0232(9) 0.0022(7) -0.0034(7) 0.0011(7) C3 0.0222(9) 0.0241(9) 0.0233(10) -0.0036(7) 0.0028(7) 0.0032(7) C4 0.0239(9) 0.0253(9) 0.0159(9) -0.0030(7) 0.0005(7) -0.0020(7) C5 0.0215(9) 0.0236(9) 0.0169(9) -0.0014(7) 0.0014(7) -0.0005(7) C6 0.0257(9) 0.0281(10) 0.0204(9) 0.0019(7) -0.0037(7) 0.0026(7) C7 0.0282(10) 0.0281(9) 0.0208(9) 0.0017(8) -0.0048(7) 0.0049(8) C8 0.0276(10) 0.0289(10) 0.0214(9) -0.0015(8) -0.0043(7) -0.0036(8) C9 0.0254(9) 0.0275(9) 0.0221(9) -0.0030(8) -0.0025(7) -0.0033(8) C10 0.0234(9) 0.0259(9) 0.0175(9) -0.0005(7) -0.0013(7) 0.0003(7) C11 0.0225(9) 0.0253(9) 0.0157(9) 0.0024(7) 0.0014(7) -0.0017(7) C12 0.0237(9) 0.0259(9) 0.0159(9) 0.0032(7) 0.0022(7) 0.0015(7) C13 0.0238(9) 0.0253(9) 0.0232(10) 0.0036(7) 0.0031(8) -0.0035(7) C14 0.0228(9) 0.0293(10) 0.0231(10) -0.0024(8) -0.0012(8) -0.0030(8) N1A 0.0412(12) 0.0500(13) 0.0787(17) -0.0278(13) -0.0232(12) 0.0146(10) C1A 0.0446(14) 0.0442(14) 0.0661(18) -0.0227(13) -0.0143(13) 0.0213(12) C2A 0.0438(15) 0.0483(15) 0.074(2) -0.0258(14) -0.0207(14) 0.0180(12) C3A 0.0450(15) 0.0492(16) 0.091(2) -0.0238(16) -0.0136(16) 0.0108(13) C4A 0.0543(17) 0.0532(16) 0.080(2) 0.0152(15) -0.0071(15) -0.0181(14) C5A 0.0561(17) 0.0571(17) 0.066(2) 0.0225(15) -0.0175(15) -0.0188(14) C6A 0.0423(15) 0.0544(17) 0.080(2) 0.0284(15) -0.0207(15) -0.0151(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.9956(14) . ? Cu1 N1 1.9956(14) 3_566 ? Cu1 O2 2.0130(13) 3_566 ? Cu1 O2 2.0130(13) . ? Cu1 O4 2.3773(13) . ? Cu1 O4 2.3773(13) 3_566 ? Cu2 O1 1.9926(14) 2_456 ? Cu2 O1 1.9926(14) . ? Cu2 N2 2.0031(14) . ? Cu2 N2 2.0031(14) 2_456 ? Cu2 O7 2.4085(14) . ? Cu2 O7 2.4085(14) 2_456 ? O3 N3 1.243(2) . ? O4 N3 1.259(2) . ? O5 N3 1.255(2) . ? O6 N5 1.248(2) . ? O7 N5 1.256(2) . ? O8 N5 1.2517(19) . ? N1 C5 1.339(2) . ? N1 C4 1.344(2) . ? N2 C11 1.341(2) . ? N2 C12 1.341(2) . ? C1 C5 1.389(2) . ? C1 C2 1.397(3) . ? C1 C6 1.434(2) . ? C2 C3 1.383(3) . ? C3 C4 1.378(3) . ? C6 C7 1.198(3) . ? C7 C8 1.376(3) 4_666 ? C8 C9 1.200(3) . ? C8 C7 1.376(3) 4_565 ? C9 C10 1.429(2) . ? C10 C11 1.391(3) . ? C10 C14 1.397(3) . ? C12 C13 1.379(3) . ? C13 C14 1.387(3) . ? N1A N1A 1.228(4) 3_476 ? N1A C1A 1.434(4) . ? C1A C2A 1.394(4) 1_565 ? C1A C6A 1.407(4) 4_565 ? C2A C3A 1.361(4) . ? C2A C1A 1.394(4) 1_545 ? C3A C4A 1.387(4) 4_565 ? C4A C3A 1.387(4) 4_666 ? C4A C5A 1.396(4) 1_565 ? C5A C6A 1.357(4) . ? C5A C4A 1.396(4) 1_545 ? C6A C1A 1.407(4) 4_666 ? 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 N1 180.00(7) . 3_566 ? N1 Cu1 O2 87.92(6) . 3_566 ? N1 Cu1 O2 92.08(6) 3_566 3_566 ? N1 Cu1 O2 92.08(6) . . ? N1 Cu1 O2 87.92(6) 3_566 . ? O2 Cu1 O2 180.00(5) 3_566 . ? N1 Cu1 O4 92.59(5) . . ? N1 Cu1 O4 87.41(5) 3_566 . ? O2 Cu1 O4 90.96(5) 3_566 . ? O2 Cu1 O4 89.04(5) . . ? N1 Cu1 O4 87.41(5) . 3_566 ? N1 Cu1 O4 92.59(5) 3_566 3_566 ? O2 Cu1 O4 89.04(5) 3_566 3_566 ? O2 Cu1 O4 90.96(5) . 3_566 ? O4 Cu1 O4 180.0 . 3_566 ? O1 Cu2 O1 90.98(8) 2_456 . ? O1 Cu2 N2 178.06(6) 2_456 . ? O1 Cu2 N2 87.63(6) . . ? O1 Cu2 N2 87.63(6) 2_456 2_456 ? O1 Cu2 N2 178.06(6) . 2_456 ? N2 Cu2 N2 93.79(8) . 2_456 ? O1 Cu2 O7 89.08(6) 2_456 . ? O1 Cu2 O7 89.81(6) . . ? N2 Cu2 O7 92.27(5) . . ? N2 Cu2 O7 88.82(5) 2_456 . ? O1 Cu2 O7 89.81(6) 2_456 2_456 ? O1 Cu2 O7 89.08(6) . 2_456 ? N2 Cu2 O7 88.82(5) . 2_456 ? N2 Cu2 O7 92.27(5) 2_456 2_456 ? O7 Cu2 O7 178.41(6) . 2_456 ? N3 O4 Cu1 128.63(11) . . ? N5 O7 Cu2 127.12(11) . . ? C5 N1 C4 118.60(15) . . ? C5 N1 Cu1 119.57(12) . . ? C4 N1 Cu1 121.77(12) . . ? C11 N2 C12 118.37(15) . . ? C11 N2 Cu2 120.05(12) . . ? C12 N2 Cu2 121.42(12) . . ? O3 N3 O5 119.98(16) . . ? O3 N3 O4 119.70(15) . . ? O5 N3 O4 120.31(16) . . ? O6 N5 O8 119.33(15) . . ? O6 N5 O7 120.21(15) . . ? O8 N5 O7 120.45(16) . . ? C5 C1 C2 118.50(16) . . ? C5 C1 C6 119.35(17) . . ? C2 C1 C6 122.15(16) . . ? C3 C2 C1 118.61(17) . . ? C4 C3 C2 119.40(18) . . ? N1 C4 C3 122.34(17) . . ? N1 C5 C1 122.52(17) . . ? C7 C6 C1 178.8(2) . . ? C6 C7 C8 179.0(2) . 4_666 ? C9 C8 C7 179.6(2) . 4_565 ? C8 C9 C10 178.5(2) . . ? C11 C10 C14 118.54(17) . . ? C11 C10 C9 119.59(17) . . ? C14 C10 C9 121.85(17) . . ? N2 C11 C10 122.63(17) . . ? N2 C12 C13 122.66(17) . . ? C12 C13 C14 119.33(18) . . ? C13 C14 C10 118.47(17) . . ? N1A N1A C1A 113.7(3) 3_476 . ? C2A C1A C6A 118.7(3) 1_565 4_565 ? C2A C1A N1A 115.7(2) 1_565 . ? C6A C1A N1A 125.5(3) 4_565 . ? C3A C2A C1A 121.0(3) . 1_545 ? C2A C3A C4A 120.2(3) . 4_565 ? C3A C4A C5A 119.2(3) 4_666 1_565 ? C6A C5A C4A 121.1(3) . 1_545 ? C5A C6A C1A 119.8(3) . 4_666 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.74 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.524 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.085 data_z34 _database_code_CSD 181464 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cu(NO3)2*2(C14H10N2)*0.29(C10H10N2)' _chemical_melting_point ? _chemical_formula_moiety '4[Cu(NO3)2],(2C14H10N2),1.16(C10H10N2)' _chemical_formula_sum 'C123.52 H73.60 Cu4 N25.92 O24' _chemical_formula_weight 639.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M C222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 14.0360(10) _cell_length_b 22.980(2) _cell_length_c 9.0330(10) _cell_angle_alpha 90.000(10) _cell_angle_beta 90.000(10) _cell_angle_gamma 90.000(10) _cell_volume 2913.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.806 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _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 17393 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 28.73 _reflns_number_total 3776 _reflns_number_gt 3468 _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^)+(0.0724P)^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 mixed _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 0.002(16) _refine_ls_number_reflns 3776 _refine_ls_number_parameters 235 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.229 _refine_ls_shift/su_max 0.413 _refine_ls_shift/su_mean 0.029 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 1.0000 0.783233(2) 0.7500 0.01743(1) Uani 1 2 d S . . O1 O 1.13002(3) 0.796045(13) 0.35411(3) 0.05927(10) Uani 1 1 d . . . O2 O 1.137401(14) 0.785676(10) 0.59286(2) 0.02970(5) Uani 1 1 d . . . O3 O 1.146603(19) 0.709897(11) 0.44893(3) 0.04505(7) Uani 1 1 d . . . N1 N 0.929515(16) 0.721756(9) 0.63159(2) 0.02033(5) Uani 1 1 d . . . N2 N 1.057155(15) 0.845778(9) 0.88026(2) 0.01869(5) Uani 1 1 d . . . N3 N 1.139332(18) 0.763902(12) 0.46314(3) 0.03130(7) Uani 1 1 d . . . C1 C 0.82986(2) 0.635312(12) 0.47962(3) 0.02565(7) Uani 1 1 d . . . C2 C 0.87389(2) 0.680073(12) 0.40396(3) 0.02624(7) Uani 1 1 d . . . H2 H 0.8702 0.6820 0.2991 0.031 Uiso 1 1 calc R . . C3 C 0.92337(2) 0.721988(12) 0.48181(3) 0.02319(6) Uani 1 1 d . . . H3 H 0.9543 0.7522 0.4284 0.028 Uiso 1 1 calc R . . C4 C 0.88544(2) 0.678326(12) 0.70554(3) 0.02768(7) Uani 1 1 d . . . H4 H 0.8896 0.6773 0.8105 0.033 Uiso 1 1 calc R . . C5 C 0.83487(2) 0.635509(13) 0.63406(3) 0.03159(8) Uani 1 1 d . . . H5 H 0.8034 0.6061 0.6895 0.038 Uiso 1 1 calc R . . C6 C 0.78097(2) 0.589322(13) 0.40415(3) 0.02849(8) Uani 1 1 d . . . C7 C 0.74362(2) 0.549930(13) 0.33922(3) 0.02990(8) Uani 1 1 d . . . C8 C 0.703385(19) 0.505884(10) 0.25684(4) 0.02764(6) Uani 1 1 d . . . C9 C 1.16985(2) 0.968703(12) 1.17914(3) 0.02942(8) Uani 1 1 d . . . C10 C 1.13217(2) 0.926302(11) 1.08011(3) 0.02395(7) Uani 1 1 d . . . C11 C 1.03368(2) 0.924245(12) 1.05042(3) 0.02595(7) Uani 1 1 d . . . H11 H 0.9917 0.9505 1.0987 0.031 Uiso 1 1 calc R . . C12 C 0.99811(2) 0.883811(9) 0.95049(3) 0.02254(6) Uani 1 1 d . . . H12 H 0.9316 0.8827 0.9309 0.027 Uiso 1 1 calc R . . C13 C 1.151681(19) 0.847833(11) 0.90809(3) 0.02184(6) Uani 1 1 d . . . H13 H 1.1928 0.8217 0.8575 0.026 Uiso 1 1 calc R . . C14 C 1.19028(2) 0.886697(12) 1.00759(3) 0.02484(7) Uani 1 1 d . . . H14 H 1.2569 0.8864 1.0265 0.030 Uiso 1 1 calc R . . N1A N 0.50829(6) 0.02489(5) -0.23359(14) 0.194(2) Uani 0.12 1 d PGU A -1 N2A N 0.51604(7) -0.01660(5) -0.14658(15) 0.194(2) Uani 0.12 1 d PGU A -1 C1A C 0.52540(6) 0.00986(5) -0.38476(14) 0.0434(8) Uani 0.12 1 d PGU A -1 C2A C 0.52773(7) 0.05650(6) -0.48361(15) 0.1187(16) Uani 0.12 1 d PGU A -1 H2A H 0.5184 0.0951 -0.4486 0.142 Uiso 0.12 1 calc PR A -1 C3A C 0.54370(8) 0.04650(7) -0.63388(14) 0.1506(12) Uani 0.12 1 d PGU A -1 H3A H 0.5453 0.0783 -0.7012 0.181 Uiso 0.12 1 calc PR A -1 C4A C 0.55740(9) -0.01015(8) -0.68539(15) 0.0657(9) Uani 0.12 1 d PGU A -1 H4A H 0.5684 -0.0170 -0.7877 0.079 Uiso 0.12 1 calc PR A -1 C5A C 0.55497(12) -0.05676(7) -0.58660(16) 0.1506(12) Uani 0.12 1 d PGU A -1 H5A H 0.5642 -0.0953 -0.6216 0.181 Uiso 0.12 1 calc PR A -1 C6A C 0.53895(10) -0.04675(6) -0.43623(15) 0.0692(8) Uani 0.12 1 d PGU A -1 H6A H 0.5373 -0.0785 -0.3689 0.083 Uiso 0.12 1 calc PR A -1 C7A C 0.49893(7) -0.00157(6) 0.00458(14) 0.0890(12) Uani 0.12 1 d PGU A -1 C8A C 0.49660(11) -0.04821(6) 0.10344(15) 0.1187(16) Uani 0.12 1 d PGDU A -1 H8A H 0.5059 -0.0868 0.0684 0.142 Uiso 0.12 1 calc PR A -1 C9A C 0.48063(11) -0.03822(8) 0.25371(15) 0.1506(12) Uani 0.12 1 d PGDU A -1 H9A H 0.4791 -0.0700 0.3210 0.181 Uiso 0.12 1 calc PR A -1 C10A C 0.46693(9) 0.01844(8) 0.30522(14) 0.0657(9) Uani 0.12 1 d PGDU A -1 H10A H 0.4560 0.0252 0.4075 0.079 Uiso 0.12 1 calc PR A -1 C11A C 0.46936(9) 0.06505(7) 0.20642(15) 0.1506(12) Uani 0.12 1 d PGDU A -1 H11A H 0.4601 0.1036 0.2415 0.181 Uiso 0.12 1 calc PR A -1 C12A C 0.48538(8) 0.05504(6) 0.05606(15) 0.0692(8) Uani 0.12 1 d PGDU A -1 H12A H 0.4871 0.0868 -0.0112 0.083 Uiso 0.12 1 calc PR A -1 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 0.02189(2) 0.01310(1) 0.01730(1) 0.000 -0.00738(2) 0.000 O1 0.0887(2) 0.05941(16) 0.02971(11) 0.01224(11) 0.00057(13) -0.00655(16) O2 0.02929(9) 0.03335(9) 0.02645(9) -0.00411(9) 0.00192(8) 0.00267(9) O3 0.06392(14) 0.04291(11) 0.02832(10) -0.00863(10) -0.00442(10) 0.02393(11) N1 0.02498(10) 0.01642(9) 0.01959(9) 0.00113(8) -0.00626(8) -0.00195(8) N2 0.02366(10) 0.01431(8) 0.01810(9) -0.00097(8) -0.00500(8) -0.00022(8) N3 0.02672(12) 0.04225(13) 0.02493(11) 0.00145(11) -0.00028(10) 0.00298(10) C1 0.02676(12) 0.02420(12) 0.02597(12) -0.00433(10) -0.00770(11) -0.00214(10) C2 0.03316(14) 0.02724(12) 0.01830(11) -0.00344(10) -0.00842(11) -0.00265(11) C3 0.03017(12) 0.02032(11) 0.01907(10) -0.00170(10) -0.00324(10) -0.00183(10) C4 0.04156(15) 0.02317(12) 0.01829(11) -0.00027(9) -0.00229(11) -0.00878(11) C5 0.04313(15) 0.02683(12) 0.02481(13) 0.00038(11) -0.00088(12) -0.01513(12) C6 0.02981(14) 0.02589(12) 0.02978(13) -0.00385(11) -0.00482(12) -0.00400(11) C7 0.03576(15) 0.02663(12) 0.02731(13) -0.00371(11) -0.00778(12) -0.00044(11) C8 0.03361(12) 0.02133(10) 0.02798(12) -0.00353(14) -0.00584(14) -0.00221(9) C9 0.03767(15) 0.02280(12) 0.02780(13) -0.00255(11) -0.00643(12) -0.00155(12) C10 0.03103(13) 0.01956(11) 0.02127(11) -0.00319(9) -0.00779(11) -0.00442(10) C11 0.03006(13) 0.02490(12) 0.02287(12) -0.00570(10) -0.00327(11) 0.00070(10) C12 0.02305(10) 0.01831(9) 0.02626(10) -0.00234(8) -0.00082(13) 0.00241(13) C13 0.02136(11) 0.02052(11) 0.02364(11) -0.00121(10) -0.00254(10) 0.00088(9) C14 0.02186(12) 0.02281(11) 0.02985(13) -0.00323(11) -0.00426(11) -0.00198(10) N1A 0.155(3) 0.110(2) 0.317(5) 0.015(4) -0.073(4) 0.044(3) N2A 0.155(3) 0.110(2) 0.317(5) 0.015(4) -0.073(4) 0.044(3) C1A 0.0315(13) 0.0275(11) 0.0712(18) -0.0167(11) 0.0211(11) 0.0089(9) C2A 0.144(3) 0.140(3) 0.072(2) 0.002(2) 0.021(2) 0.031(3) C3A 0.0283(8) 0.278(3) 0.146(2) 0.023(2) 0.0543(9) 0.0010(14) C4A 0.0631(13) 0.0440(12) 0.090(2) -0.0066(14) -0.0027(13) -0.0296(9) C5A 0.0283(8) 0.278(3) 0.146(2) 0.023(2) 0.0543(9) 0.0010(14) C6A 0.0384(13) 0.0934(16) 0.0759(13) -0.0005(17) -0.0283(11) -0.0203(11) C7A 0.0841(18) 0.0513(13) 0.132(3) -0.0024(16) -0.005(8) 0.011(6) C8A 0.144(3) 0.140(3) 0.072(2) 0.002(2) 0.021(2) 0.031(3) C9A 0.0283(8) 0.278(3) 0.146(2) 0.023(2) 0.0543(9) 0.0010(14) C10A 0.0631(13) 0.0440(12) 0.090(2) -0.0066(14) -0.0027(13) -0.0296(9) C11A 0.0283(8) 0.278(3) 0.146(2) 0.023(2) 0.0543(9) 0.0010(14) C12A 0.0384(13) 0.0934(16) 0.0759(13) -0.0005(17) -0.0283(11) -0.0203(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N2 2.0233(3) . ? Cu1 N2 2.0233(3) 3_756 ? Cu1 N1 2.0295(3) . ? Cu1 N1 2.0295(3) 3_756 ? Cu1 O2 2.3953(3) . ? Cu1 O2 2.3953(3) 3_756 ? O1 N3 1.2380(4) . ? O2 N3 1.2744(4) . ? O3 N3 1.2518(4) . ? N1 C4 1.3509(4) . ? N1 C3 1.3557(4) . ? N2 C13 1.3512(4) . ? N2 C12 1.3614(4) . ? C1 C2 1.3810(4) . ? C1 C5 1.3968(4) . ? C1 C6 1.4327(4) . ? C2 C3 1.3801(4) . ? C4 C5 1.3744(4) . ? C6 C7 1.1992(4) . ? C7 C8 1.3774(4) . ? C8 C9 1.2018(4) 5_444 ? C9 C8 1.2018(4) 5_556 ? C9 C10 1.4245(4) . ? C10 C14 1.3866(4) . ? C10 C11 1.4090(4) . ? C11 C12 1.3883(4) . ? C13 C14 1.3780(4) . ? N1A N2A 1.2404 . ? N1A C1A 1.4288 . ? N2A C7A 1.4288 . ? C1A C6A 1.3946 . ? C1A C2A 1.3954 . ? C2A C3A 1.3948 . ? C3A C4A 1.3958 . ? C4A C5A 1.3946 . ? C5A C6A 1.3958 . ? C7A C12A 1.3944 . ? C7A C8A 1.3954 . ? C8A C9A 1.3948 . ? C9A C10A 1.3958 . ? C10A C11A 1.3946 . ? C11A C12A 1.3959 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Cu1 N2 89.470(14) . 3_756 ? N2 Cu1 N1 173.866(9) . . ? N2 Cu1 N1 89.697(12) 3_756 . ? N2 Cu1 N1 89.697(11) . 3_756 ? N2 Cu1 N1 173.866(9) 3_756 3_756 ? N1 Cu1 N1 91.768(15) . 3_756 ? N2 Cu1 O2 90.500(12) . . ? N2 Cu1 O2 87.591(12) 3_756 . ? N1 Cu1 O2 95.536(12) . . ? N1 Cu1 O2 86.340(12) 3_756 . ? N2 Cu1 O2 87.591(12) . 3_756 ? N2 Cu1 O2 90.500(12) 3_756 3_756 ? N1 Cu1 O2 86.340(12) . 3_756 ? N1 Cu1 O2 95.536(12) 3_756 3_756 ? O2 Cu1 O2 177.313(11) . 3_756 ? N3 O2 Cu1 123.559(18) . . ? C4 N1 C3 117.86(2) . . ? C4 N1 Cu1 118.480(19) . . ? C3 N1 Cu1 123.66(2) . . ? C13 N2 C12 119.25(2) . . ? C13 N2 Cu1 121.490(19) . . ? C12 N2 Cu1 119.06(2) . . ? O1 N3 O3 121.23(3) . . ? O1 N3 O2 119.67(3) . . ? O3 N3 O2 119.03(3) . . ? C2 C1 C5 117.99(3) . . ? C2 C1 C6 121.89(3) . . ? C5 C1 C6 120.12(3) . . ? C3 C2 C1 119.53(3) . . ? N1 C3 C2 122.54(3) . . ? N1 C4 C5 122.21(3) . . ? C4 C5 C1 119.84(3) . . ? C7 C6 C1 177.30(3) . . ? C6 C7 C8 176.49(3) . . ? C9 C8 C7 176.95(4) 5_444 . ? C8 C9 C10 176.82(3) 5_556 . ? C14 C10 C11 117.72(3) . . ? C14 C10 C9 121.82(3) . . ? C11 C10 C9 120.45(3) . . ? C12 C11 C10 119.94(3) . . ? N2 C12 C11 120.91(3) . . ? N2 C13 C14 122.01(3) . . ? C13 C14 C10 120.15(3) . . ? N2A N1A C1A 113.9 . . ? N1A N2A C7A 113.9 . . ? C6A C1A C2A 120.0 . . ? C6A C1A N1A 124.5 . . ? C2A C1A N1A 115.5 . . ? C3A C2A C1A 120.0 . . ? C2A C3A C4A 120.0 . . ? C5A C4A C3A 120.0 . . ? C4A C5A C6A 120.0 . . ? C1A C6A C5A 120.0 . . ? C12A C7A C8A 120.0 . . ? C12A C7A N2A 124.5 . . ? C8A C7A N2A 115.5 . . ? C9A C8A C7A 120.0 . . ? C8A C9A C10A 120.0 . . ? C11A C10A C9A 120.0 . . ? C10A C11A C12A 120.0 . . ? C7A C12A C11A 120.0 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.73 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.745 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.091