# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name S.Das _publ_contact_author_name 'Dr. Samar K. Das' _publ_contact_author_email skdsc@uohyd.ernet.in data_sd7 _database_code_depnum_ccdc_archive 'CCDC 675111' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 Cu N4 O4 S, O1.37' _chemical_formula_sum 'C12 H18 Cu N4 O5 S' _chemical_formula_weight 393.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.6001(12) _cell_length_b 7.5076(5) _cell_length_c 21.9761(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3068.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7175 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 28.22 _exptl_crystal_description Needle _exptl_crystal_colour Purple _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 1.591 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.5282 _exptl_absorpt_correction_T_max 0.9391 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Area Detector' _diffrn_measurement_method 'Phi and Omega Scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17929 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.24 _reflns_number_total 3632 _reflns_number_gt 3159 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0357P)^2^+3.5997P] 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 3632 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 O4 O 0.18698(9) 0.0393(2) 0.32219(8) 0.0176(4) Uani 1 1 d . . . Cu1 Cu 0.089242(15) 0.59216(4) 0.299379(13) 0.01250(10) Uani 1 1 d . . . C1 C 0.17983(13) 0.6725(3) 0.19857(11) 0.0145(5) Uani 1 1 d . . . C2 C 0.23492(14) 0.7368(3) 0.16165(12) 0.0184(5) Uani 1 1 d . . . H2 H 0.2731 0.7995 0.1786 0.022 Uiso 1 1 calc R . . C3 C 0.23241(14) 0.7068(3) 0.09958(12) 0.0195(5) Uani 1 1 d . . . H3 H 0.2691 0.7496 0.0748 0.023 Uiso 1 1 calc R . . C4 C 0.17573(14) 0.6134(3) 0.07390(12) 0.0183(5) Uani 1 1 d . . . H4 H 0.1747 0.5932 0.0322 0.022 Uiso 1 1 calc R . . C5 C 0.12053(13) 0.5500(3) 0.11043(12) 0.0159(5) Uani 1 1 d . . . H5 H 0.0821 0.4886 0.0933 0.019 Uiso 1 1 calc R . . C6 C 0.12305(13) 0.5789(3) 0.17284(11) 0.0137(5) Uani 1 1 d . . . C7 C 0.03189(13) 0.6939(3) 0.41490(11) 0.0153(5) Uani 1 1 d . . . C8 C 0.02037(15) 0.7735(3) 0.47096(12) 0.0199(5) Uani 1 1 d . . . H8 H 0.0549 0.8496 0.4872 0.024 Uiso 1 1 calc R . . C9 C -0.04231(15) 0.7400(4) 0.50277(12) 0.0223(6) Uani 1 1 d . . . H9 H -0.0496 0.7916 0.5407 0.027 Uiso 1 1 calc R . . C10 C -0.09463(15) 0.6286(4) 0.47792(13) 0.0216(6) Uani 1 1 d . . . H10 H -0.1370 0.6070 0.4992 0.026 Uiso 1 1 calc R . . C11 C -0.08369(14) 0.5503(3) 0.42174(12) 0.0190(5) Uani 1 1 d . . . H11 H -0.1188 0.4772 0.4049 0.023 Uiso 1 1 calc R . . C12 C -0.02004(13) 0.5811(3) 0.39058(11) 0.0144(5) Uani 1 1 d . . . N1 N 0.17912(12) 0.6962(3) 0.26390(10) 0.0149(4) Uani 1 1 d . . . N2 N 0.06867(11) 0.5106(3) 0.21382(10) 0.0136(4) Uani 1 1 d . . . N3 N 0.09617(12) 0.7239(3) 0.37907(10) 0.0173(5) Uani 1 1 d . . . N4 N -0.00394(12) 0.4967(3) 0.33291(10) 0.0149(4) Uani 1 1 d . . . O1 O 0.14968(9) 0.3454(2) 0.32478(8) 0.0185(4) Uani 1 1 d . . . O2 O 0.06377(10) 0.1111(2) 0.34631(8) 0.0190(4) Uani 1 1 d . . . O3 O 0.10787(10) 0.1521(2) 0.24419(8) 0.0192(4) Uani 1 1 d . . . O5A O 0.2293(6) 0.4278(19) 0.4298(5) 0.054(3) Uani 0.32 1 d P . . O5B O 0.2397(4) 0.6497(16) 0.4303(4) 0.0445(18) Uani 0.38 1 d P . . O5D O 0.2483(7) 0.280(3) 0.4254(5) 0.054(3) Uani 0.24 1 d P . . O5E O 0.2301(5) 0.5323(14) 0.4277(4) 0.049(2) Uani 0.43 1 d P . . S1 S 0.12682(3) 0.16232(8) 0.30921(3) 0.01233(13) Uani 1 1 d . . . H2A H 0.0720(16) 0.395(4) 0.2147(13) 0.013(7) Uiso 1 1 d . . . H4B H 0.0002(16) 0.384(4) 0.3398(13) 0.016(7) Uiso 1 1 d . . . H3B H 0.1024(17) 0.840(5) 0.3718(14) 0.022(8) Uiso 1 1 d . . . H2B H 0.026(2) 0.523(5) 0.1966(14) 0.029(9) Uiso 1 1 d . . . H1A H 0.1863(17) 0.809(5) 0.2737(14) 0.024(8) Uiso 1 1 d . . . H4A H -0.0379(18) 0.515(4) 0.3097(14) 0.022(8) Uiso 1 1 d . . . H3A H 0.1325(18) 0.685(4) 0.3950(14) 0.020(8) Uiso 1 1 d . . . H1B H 0.2136(18) 0.644(4) 0.2816(14) 0.021(8) Uiso 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 O4 0.0121(8) 0.0127(8) 0.0280(10) -0.0013(7) -0.0034(7) 0.0034(7) Cu1 0.00941(15) 0.01141(16) 0.01670(16) -0.00108(11) -0.00108(11) 0.00035(11) C1 0.0122(11) 0.0108(11) 0.0206(13) 0.0001(9) -0.0017(10) 0.0027(9) C2 0.0131(12) 0.0122(12) 0.0300(14) -0.0014(10) 0.0012(11) -0.0001(10) C3 0.0136(12) 0.0187(13) 0.0263(14) 0.0045(10) 0.0049(11) 0.0005(10) C4 0.0188(13) 0.0184(13) 0.0177(13) 0.0007(10) 0.0015(10) 0.0035(10) C5 0.0129(12) 0.0147(12) 0.0202(12) 0.0001(9) -0.0018(10) -0.0015(9) C6 0.0090(11) 0.0107(11) 0.0213(13) 0.0016(9) -0.0003(10) 0.0006(9) C7 0.0144(12) 0.0148(12) 0.0167(12) 0.0025(9) -0.0018(10) 0.0047(9) C8 0.0220(14) 0.0177(12) 0.0199(13) -0.0012(10) -0.0073(11) 0.0040(10) C9 0.0293(15) 0.0217(13) 0.0158(13) 0.0006(10) -0.0013(11) 0.0100(12) C10 0.0203(13) 0.0215(14) 0.0229(14) 0.0053(10) 0.0041(11) 0.0058(10) C11 0.0169(13) 0.0155(12) 0.0245(14) 0.0035(10) 0.0007(11) 0.0000(10) C12 0.0158(11) 0.0118(11) 0.0157(11) 0.0033(9) -0.0010(9) 0.0049(9) N1 0.0112(10) 0.0125(11) 0.0210(11) -0.0022(8) -0.0015(9) 0.0004(8) N2 0.0087(10) 0.0132(11) 0.0189(11) 0.0021(8) -0.0011(8) -0.0017(8) N3 0.0128(11) 0.0187(12) 0.0204(11) 0.0005(9) -0.0019(9) -0.0018(9) N4 0.0121(10) 0.0129(11) 0.0196(11) 0.0004(8) -0.0021(9) 0.0006(8) O1 0.0160(9) 0.0109(8) 0.0287(10) -0.0025(7) -0.0065(8) 0.0012(7) O2 0.0140(8) 0.0227(10) 0.0201(9) -0.0011(7) 0.0023(7) -0.0016(7) O3 0.0207(9) 0.0178(9) 0.0190(9) -0.0009(7) -0.0010(7) -0.0030(7) O5A 0.043(6) 0.072(8) 0.048(6) -0.024(7) 0.016(5) -0.012(7) O5B 0.032(4) 0.057(5) 0.045(4) 0.010(5) -0.004(3) 0.007(5) O5D 0.042(7) 0.077(10) 0.044(7) 0.006(8) -0.002(5) -0.006(7) O5E 0.052(5) 0.052(5) 0.043(4) 0.033(6) 0.017(4) 0.024(6) S1 0.0094(3) 0.0104(3) 0.0172(3) -0.0016(2) -0.0011(2) 0.0006(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 O4 S1 1.4789(18) . ? Cu1 N1 2.003(2) . ? Cu1 N2 2.014(2) . ? Cu1 N4 2.015(2) . ? Cu1 N3 2.015(2) . ? Cu1 O1 2.2376(18) . ? C1 C6 1.389(3) . ? C1 C2 1.393(4) . ? C1 N1 1.447(3) . ? C2 C3 1.383(4) . ? C2 H2 0.9300 . ? C3 C4 1.386(4) . ? C3 H3 0.9300 . ? C4 C5 1.387(4) . ? C4 H4 0.9300 . ? C5 C6 1.389(4) . ? C5 H5 0.9300 . ? C6 N2 1.448(3) . ? C7 C8 1.386(4) . ? C7 C12 1.391(3) . ? C7 N3 1.449(3) . ? C8 C9 1.383(4) . ? C8 H8 0.9300 . ? C9 C10 1.394(4) . ? C9 H9 0.9300 . ? C10 C11 1.383(4) . ? C10 H10 0.9300 . ? C11 C12 1.387(4) . ? C11 H11 0.9300 . ? C12 N4 1.448(3) . ? N1 H1A 0.89(3) . ? N1 H1B 0.85(3) . ? N2 H2A 0.87(3) . ? N2 H2B 0.88(4) . ? N3 H3B 0.89(4) . ? N3 H3A 0.81(3) . ? N4 H4B 0.86(3) . ? N4 H4A 0.82(3) . ? O1 S1 1.4789(18) . ? O2 S1 1.4792(19) . ? O3 S1 1.4737(19) . ? O5A O5E 0.786(12) . ? O5A O5D 1.167(17) . ? O5A O5B 1.677(14) . ? O5B O5E 0.901(10) . ? O5B O5D 1.011(16) 8_665 ? O5D O5B 1.011(16) 8_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 N1 Cu1 N2 85.05(9) . . ? N1 Cu1 N4 177.20(10) . . ? N2 Cu1 N4 94.01(9) . . ? N1 Cu1 N3 95.37(9) . . ? N2 Cu1 N3 166.54(10) . . ? N4 Cu1 N3 84.93(9) . . ? N1 Cu1 O1 90.03(8) . . ? N2 Cu1 O1 94.40(8) . . ? N4 Cu1 O1 92.67(8) . . ? N3 Cu1 O1 99.05(9) . . ? C6 C1 C2 119.8(2) . . ? C6 C1 N1 117.3(2) . . ? C2 C1 N1 122.8(2) . . ? C3 C2 C1 119.5(2) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.6(2) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 119.5(2) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 120.4(2) . . ? C1 C6 N2 117.2(2) . . ? C5 C6 N2 122.3(2) . . ? C8 C7 C12 119.8(2) . . ? C8 C7 N3 122.9(2) . . ? C12 C7 N3 117.3(2) . . ? C9 C8 C7 120.1(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.1(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 119.7(2) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C7 120.3(2) . . ? C11 C12 N4 122.4(2) . . ? C7 C12 N4 117.3(2) . . ? C1 N1 Cu1 110.24(16) . . ? C1 N1 H1A 111(2) . . ? Cu1 N1 H1A 114(2) . . ? C1 N1 H1B 113(2) . . ? Cu1 N1 H1B 106(2) . . ? H1A N1 H1B 102(3) . . ? C6 N2 Cu1 109.89(16) . . ? C6 N2 H2A 109(2) . . ? Cu1 N2 H2A 105.5(19) . . ? C6 N2 H2B 109(2) . . ? Cu1 N2 H2B 123(2) . . ? H2A N2 H2B 100(3) . . ? C7 N3 Cu1 110.08(16) . . ? C7 N3 H3B 111(2) . . ? Cu1 N3 H3B 109(2) . . ? C7 N3 H3A 113(2) . . ? Cu1 N3 H3A 105(2) . . ? H3B N3 H3A 108(3) . . ? C12 N4 Cu1 110.02(16) . . ? C12 N4 H4B 107.2(19) . . ? Cu1 N4 H4B 110(2) . . ? C12 N4 H4A 108(2) . . ? Cu1 N4 H4A 112(2) . . ? H4B N4 H4A 110(3) . . ? S1 O1 Cu1 124.57(10) . . ? O5E O5A O5D 159.6(17) . . ? O5E O5A O5B 6.7(10) . . ? O5D O5A O5B 155.4(11) . . ? O5E O5B O5D 170.1(13) . 8_665 ? O5E O5B O5A 5.9(8) . . ? O5D O5B O5A 171.0(11) 8_665 . ? O5B O5D O5A 168.0(15) 8_655 . ? O5A O5E O5B 167.4(18) . . ? O3 S1 O1 109.96(11) . . ? O3 S1 O4 109.61(11) . . ? O1 S1 O4 108.57(10) . . ? O3 S1 O2 109.35(11) . . ? O1 S1 O2 110.00(11) . . ? O4 S1 O2 109.34(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A O3 0.82(3) 2.04(3) 2.823(3) 159(3) 3 N3 H3B O2 0.89(4) 2.23(4) 3.055(3) 153(3) 1_565 N2 H2B O2 0.88(4) 2.03(4) 2.895(3) 166(3) 3 N1 H1A O4 0.89(3) 2.03(3) 2.880(3) 161(3) 1_565 N1 H1B O4 0.85(3) 2.20(4) 3.038(3) 172(3) 8_665 N4 H4B O2 0.86(3) 2.37(3) 3.171(3) 154(3) . N2 H2A O3 0.87(3) 2.05(3) 2.867(3) 157(3) . _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 1.022 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.086 #***********************End of Crystal data of Compound 1********************* #***************Crystal data of Compound 2***************************** data_s99 _database_code_depnum_ccdc_archive 'CCDC 675112' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 Cu N8' _chemical_formula_sum 'C6 H8 Cu N8' _chemical_formula_weight 255.74 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' 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 'P2(1)2(1)2(1) ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.9976(4) _cell_length_b 7.8816(6) _cell_length_c 19.2462(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 909.78(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2818 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 28.32 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.867 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 2.379 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6476 _exptl_absorpt_correction_T_max 0.9108 _exptl_absorpt_process_details 'Bruker 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5665 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.51 _reflns_number_total 2112 _reflns_number_gt 2013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.0' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0339P)^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 0.007(16) _refine_ls_number_reflns 2112 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0669 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.002 _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 0.22937(5) 0.15113(4) 0.189195(16) 0.01143(10) Uani 1 1 d . . . C1 C -0.0556(5) 0.0107(3) 0.08538(16) 0.0110(6) Uani 1 1 d . . . C2 C -0.2212(5) -0.0821(3) 0.05110(15) 0.0140(6) Uani 1 1 d . . . C3 C -0.2061(5) -0.1103(3) -0.01970(16) 0.0162(6) Uani 1 1 d . . . C4 C -0.0238(5) -0.0497(4) -0.05683(16) 0.0168(6) Uani 1 1 d . . . C5 C 0.1414(5) 0.0411(4) -0.02309(16) 0.0153(6) Uani 1 1 d . . . C6 C 0.1243(5) 0.0716(3) 0.04744(15) 0.0129(6) Uani 1 1 d . . . N1 N -0.0599(4) 0.0394(3) 0.15928(13) 0.0117(5) Uani 1 1 d . . . N2 N 0.2914(4) 0.1623(3) 0.08633(12) 0.0130(5) Uani 1 1 d . . . N3 N 0.1404(4) 0.1693(3) 0.28780(12) 0.0144(5) Uani 1 1 d . . . N4 N 0.0475(4) 0.0527(3) 0.31522(13) 0.0131(5) Uani 1 1 d . . . N5 N -0.0402(5) -0.0581(3) 0.34371(14) 0.0215(6) Uani 1 1 d . . . N6 N 0.5339(4) 0.2416(3) 0.20699(13) 0.0165(5) Uani 1 1 d . . . N7 N 0.5800(4) 0.2977(3) 0.26319(13) 0.0138(5) Uani 1 1 d . . . N8 N 0.6305(4) 0.3542(3) 0.31617(13) 0.0176(5) Uani 1 1 d . . . H2 H -0.327(5) -0.133(4) 0.0755(16) 0.016(8) Uiso 1 1 d . . . H3 H -0.313(5) -0.166(4) -0.0411(15) 0.008(7) Uiso 1 1 d . . . H4 H -0.016(5) -0.052(4) -0.1081(18) 0.015(8) Uiso 1 1 d . . . H5 H 0.255(7) 0.076(5) -0.0449(18) 0.030(10) Uiso 1 1 d . . . H1A H -0.171(7) 0.101(5) 0.1704(18) 0.032(11) Uiso 1 1 d . . . H1B H -0.076(5) -0.066(5) 0.1765(17) 0.021(9) Uiso 1 1 d . . . H2B H 0.427(7) 0.133(5) 0.068(2) 0.039(11) Uiso 1 1 d . . . H2A H 0.288(6) 0.253(5) 0.0784(19) 0.026(10) Uiso 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 0.01014(15) 0.01354(16) 0.01063(16) -0.00098(14) 0.00057(12) -0.00230(13) C1 0.0147(13) 0.0076(13) 0.0107(14) -0.0003(9) -0.0014(12) 0.0026(10) C2 0.0151(14) 0.0090(12) 0.0180(14) 0.0002(10) -0.0017(12) -0.0019(11) C3 0.0162(14) 0.0149(14) 0.0174(14) -0.0009(11) -0.0058(12) -0.0005(11) C4 0.0250(16) 0.0118(13) 0.0136(16) -0.0024(12) -0.0054(12) 0.0051(12) C5 0.0164(14) 0.0117(13) 0.0176(16) 0.0024(12) 0.0011(12) 0.0018(11) C6 0.0138(13) 0.0068(13) 0.0182(15) 0.0030(11) -0.0013(11) 0.0024(10) N1 0.0115(11) 0.0099(12) 0.0138(13) -0.0002(10) 0.0013(9) 0.0000(10) N2 0.0133(11) 0.0111(12) 0.0145(11) 0.0002(10) 0.0006(9) -0.0024(11) N3 0.0178(11) 0.0131(12) 0.0124(12) -0.0018(10) 0.0020(9) -0.0031(10) N4 0.0132(10) 0.0145(11) 0.0115(12) -0.0055(11) -0.0032(11) 0.0015(9) N5 0.0275(14) 0.0167(13) 0.0202(14) -0.0013(11) 0.0063(11) -0.0046(11) N6 0.0124(12) 0.0219(13) 0.0152(13) -0.0064(10) 0.0005(10) -0.0010(10) N7 0.0095(12) 0.0123(12) 0.0197(14) 0.0013(10) 0.0009(10) -0.0002(8) N8 0.0158(10) 0.0200(12) 0.0171(13) -0.0039(13) 0.0008(10) -0.0037(10) _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 N3 1.976(2) . ? Cu1 N6 1.990(2) . ? Cu1 N2 2.016(2) . ? Cu1 N1 2.029(2) . ? C1 C6 1.388(4) . ? C1 C2 1.399(4) . ? C1 N1 1.440(4) . ? C2 C3 1.384(4) . ? C2 H2 0.88(3) . ? C3 C4 1.391(4) . ? C3 H3 0.88(3) . ? C4 C5 1.384(4) . ? C4 H4 0.99(3) . ? C5 C6 1.382(4) . ? C5 H5 0.85(4) . ? C6 N2 1.441(4) . ? N1 H1A 0.85(4) . ? N1 H1B 0.90(4) . ? N2 H2B 0.91(4) . ? N2 H2A 0.73(4) . ? N3 N4 1.197(3) . ? N4 N5 1.157(3) . ? N6 N7 1.201(3) . ? N7 N8 1.153(3) . ? 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 N3 Cu1 N6 93.24(10) . . ? N3 Cu1 N2 171.65(11) . . ? N6 Cu1 N2 89.08(10) . . ? N3 Cu1 N1 94.19(10) . . ? N6 Cu1 N1 171.47(10) . . ? N2 Cu1 N1 84.15(10) . . ? C6 C1 C2 119.0(3) . . ? C6 C1 N1 118.6(3) . . ? C2 C1 N1 122.3(3) . . ? C3 C2 C1 120.2(3) . . ? C3 C2 H2 120(2) . . ? C1 C2 H2 120(2) . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 119.6(19) . . ? C4 C3 H3 120.3(19) . . ? C5 C4 C3 120.0(3) . . ? C5 C4 H4 116.3(19) . . ? C3 C4 H4 123.0(18) . . ? C6 C5 C4 119.8(3) . . ? C6 C5 H5 119(2) . . ? C4 C5 H5 121(2) . . ? C5 C6 C1 120.9(3) . . ? C5 C6 N2 123.0(3) . . ? C1 C6 N2 116.0(3) . . ? C1 N1 Cu1 109.44(18) . . ? C1 N1 H1A 111(2) . . ? Cu1 N1 H1A 111(3) . . ? C1 N1 H1B 103(2) . . ? Cu1 N1 H1B 113(2) . . ? H1A N1 H1B 110(3) . . ? C6 N2 Cu1 111.11(18) . . ? C6 N2 H2B 107(3) . . ? Cu1 N2 H2B 122(3) . . ? C6 N2 H2A 111(3) . . ? Cu1 N2 H2A 104(3) . . ? H2B N2 H2A 101(4) . . ? N4 N3 Cu1 119.56(19) . . ? N5 N4 N3 177.9(3) . . ? N7 N6 Cu1 119.9(2) . . ? N8 N7 N6 177.7(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N6 0.85(4) 2.20(4) 3.052(4) 174(3) 1_455 N1 H1B N3 0.90(4) 2.23(4) 3.128(4) 175(3) 3_545 _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 28.51 _diffrn_measured_fraction_theta_full 0.943 _refine_diff_density_max 0.804 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.097 #**************End of Crystal data of Compound 2*******************************