# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_ig185dx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H28 Cl2 Cu2 N8 O12, 2(Cl O4)' _chemical_formula_sum 'C32 H28 Cl4 Cu2 N8 O20' _chemical_formula_weight 1113.50 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1560(2) _cell_length_b 10.4612(3) _cell_length_c 12.4373(4) _cell_angle_alpha 70.1270(10) _cell_angle_beta 84.695(2) _cell_angle_gamma 79.552(2) _cell_volume 980.88(5) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4666 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 31.51 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.885 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 562 _exptl_absorpt_coefficient_mu 1.454 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7640 _exptl_absorpt_correction_T_max 0.8537 _exptl_absorpt_process_details 'SADABS v.2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19451 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4497 _reflns_number_gt 3756 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Crystal Impact GbR, 2006)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0296P)^2^+1.1453P] 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 4497 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0781 _refine_ls_wR_factor_gt 0.0730 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.57132(3) 0.36419(3) -0.03397(2) 0.01419(9) Uani 1 1 d . . . Cl1 Cl 0.96874(7) 0.27570(6) -0.18455(5) 0.01720(12) Uani 1 1 d . . . Cl2 Cl 0.75067(7) 0.81251(6) -0.45773(5) 0.01922(13) Uani 1 1 d . . . O1 O 0.42412(19) 0.41243(15) -0.16124(14) 0.0168(3) Uani 1 1 d . . . O2 O 0.62094(19) 0.54880(15) -0.10594(13) 0.0150(3) Uani 1 1 d . . . O3 O 0.7896(2) 0.30459(18) -0.19461(15) 0.0239(4) Uani 1 1 d . . . O4 O 1.0288(2) 0.38564(19) -0.16534(17) 0.0287(4) Uani 1 1 d . . . O5 O 1.0141(2) 0.14896(18) -0.09336(16) 0.0298(4) Uani 1 1 d . . . O6 O 1.0418(2) 0.25972(18) -0.29227(14) 0.0219(4) Uani 1 1 d . . . O7 O 0.8637(2) 0.68716(18) -0.40674(16) 0.0285(4) Uani 1 1 d . . . O8 O 0.6466(2) 0.7907(2) -0.53485(16) 0.0326(4) Uani 1 1 d . . . O9 O 0.6469(2) 0.84816(17) -0.36669(14) 0.0220(4) Uani 1 1 d . . . O10 O 0.8437(3) 0.92173(19) -0.51607(17) 0.0348(5) Uani 1 1 d . . . N1 N 0.5472(2) 0.6002(2) -0.20950(16) 0.0146(4) Uani 1 1 d . . . H1A H 0.573(4) 0.675(3) -0.257(3) 0.026(8) Uiso 1 1 d . . . N2 N 0.1878(3) 0.6755(2) -0.53885(18) 0.0213(4) Uani 1 1 d . . . H2A H 0.132(3) 0.706(3) -0.599(2) 0.018(7) Uiso 1 1 d . . . N3 N 0.7530(2) 0.29540(19) 0.07552(16) 0.0141(4) Uani 1 1 d . . . N4 N 0.5057(2) 0.18437(18) 0.04970(16) 0.0140(4) Uani 1 1 d . . . C1 C 0.4473(3) 0.5285(2) -0.23298(19) 0.0143(4) Uani 1 1 d . . . C2 C 0.3594(3) 0.5845(2) -0.34285(19) 0.0150(4) Uani 1 1 d . . . C3 C 0.3233(3) 0.7248(2) -0.4026(2) 0.0171(5) Uani 1 1 d . . . H3 H 0.3595 0.7897 -0.3758 0.021 Uiso 1 1 calc R . . C4 C 0.2345(3) 0.7684(2) -0.5007(2) 0.0210(5) Uani 1 1 d . . . H4 H 0.2063 0.8639 -0.5413 0.025 Uiso 1 1 calc R . . C5 C 0.2220(3) 0.5396(3) -0.4845(2) 0.0233(5) Uani 1 1 d . . . H5 H 0.1875 0.4772 -0.5149 0.028 Uiso 1 1 calc R . . C6 C 0.3074(3) 0.4910(2) -0.3846(2) 0.0195(5) Uani 1 1 d . . . H6 H 0.3306 0.3949 -0.3445 0.023 Uiso 1 1 calc R . . C11 C 0.8722(3) 0.3644(2) 0.0840(2) 0.0164(5) Uani 1 1 d . . . H11 H 0.8686 0.4577 0.0366 0.020 Uiso 1 1 calc R . . C12 C 1.0003(3) 0.3035(2) 0.1600(2) 0.0188(5) Uani 1 1 d . . . H12 H 1.0822 0.3545 0.1661 0.023 Uiso 1 1 calc R . . C13 C 1.0060(3) 0.1668(2) 0.2267(2) 0.0198(5) Uani 1 1 d . . . H13 H 1.0941 0.1220 0.2780 0.024 Uiso 1 1 calc R . . C14 C 0.8830(3) 0.0949(2) 0.2185(2) 0.0176(5) Uani 1 1 d . . . H14 H 0.8857 0.0010 0.2640 0.021 Uiso 1 1 calc R . . C15 C 0.7562(3) 0.1626(2) 0.14290(19) 0.0142(4) Uani 1 1 d . . . C16 C 0.6114(3) 0.1011(2) 0.13168(19) 0.0141(4) Uani 1 1 d . . . C17 C 0.5807(3) -0.0282(2) 0.2000(2) 0.0179(5) Uani 1 1 d . . . H17 H 0.6566 -0.0861 0.2567 0.022 Uiso 1 1 calc R . . C18 C 0.4360(3) -0.0713(2) 0.1838(2) 0.0206(5) Uani 1 1 d . . . H18 H 0.4126 -0.1599 0.2293 0.025 Uiso 1 1 calc R . . C19 C 0.3266(3) 0.0148(2) 0.1015(2) 0.0187(5) Uani 1 1 d . . . H19 H 0.2266 -0.0130 0.0905 0.022 Uiso 1 1 calc R . . C20 C 0.3652(3) 0.1425(2) 0.0353(2) 0.0171(5) Uani 1 1 d . . . H20 H 0.2907 0.2020 -0.0218 0.021 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 0.01502(14) 0.01153(14) 0.01495(15) -0.00132(11) -0.00491(10) -0.00316(10) Cl1 0.0165(3) 0.0190(3) 0.0176(3) -0.0072(2) -0.0025(2) -0.0036(2) Cl2 0.0217(3) 0.0207(3) 0.0155(3) -0.0048(2) 0.0010(2) -0.0071(2) O1 0.0170(8) 0.0145(8) 0.0174(8) -0.0014(7) -0.0042(6) -0.0046(6) O2 0.0169(8) 0.0159(8) 0.0116(8) -0.0024(6) -0.0057(6) -0.0030(6) O3 0.0141(8) 0.0313(10) 0.0296(10) -0.0142(8) -0.0017(7) -0.0031(7) O4 0.0302(10) 0.0288(10) 0.0366(11) -0.0188(9) -0.0008(8) -0.0134(8) O5 0.0351(10) 0.0259(10) 0.0227(10) -0.0006(8) -0.0082(8) -0.0018(8) O6 0.0202(8) 0.0287(9) 0.0173(9) -0.0097(7) -0.0013(7) -0.0007(7) O7 0.0288(10) 0.0253(9) 0.0308(11) -0.0097(8) -0.0055(8) 0.0005(7) O8 0.0314(10) 0.0487(12) 0.0222(10) -0.0160(9) -0.0061(8) -0.0071(9) O9 0.0245(9) 0.0234(9) 0.0200(9) -0.0092(7) 0.0032(7) -0.0066(7) O10 0.0427(11) 0.0280(10) 0.0319(11) -0.0046(9) 0.0137(9) -0.0190(9) N1 0.0163(9) 0.0151(9) 0.0109(9) -0.0013(8) -0.0032(7) -0.0031(7) N2 0.0206(10) 0.0270(11) 0.0165(11) -0.0062(9) -0.0082(9) -0.0025(8) N3 0.0140(9) 0.0152(9) 0.0134(9) -0.0047(8) -0.0007(7) -0.0027(7) N4 0.0142(9) 0.0143(9) 0.0144(10) -0.0057(8) -0.0031(7) -0.0014(7) C1 0.0129(10) 0.0153(10) 0.0137(11) -0.0046(9) 0.0000(8) -0.0006(8) C2 0.0123(10) 0.0183(11) 0.0139(11) -0.0046(9) 0.0001(8) -0.0026(8) C3 0.0179(11) 0.0172(11) 0.0163(12) -0.0055(9) -0.0014(9) -0.0029(9) C4 0.0223(12) 0.0192(12) 0.0202(13) -0.0039(10) -0.0042(10) -0.0034(9) C5 0.0252(13) 0.0242(13) 0.0237(13) -0.0103(11) -0.0052(10) -0.0046(10) C6 0.0201(12) 0.0169(11) 0.0212(12) -0.0049(10) -0.0040(9) -0.0038(9) C11 0.0167(11) 0.0172(11) 0.0166(12) -0.0070(9) 0.0008(9) -0.0043(8) C12 0.0157(11) 0.0233(12) 0.0208(12) -0.0110(10) -0.0028(9) -0.0037(9) C13 0.0183(11) 0.0214(12) 0.0204(12) -0.0086(10) -0.0073(9) 0.0021(9) C14 0.0216(12) 0.0140(11) 0.0161(12) -0.0050(9) -0.0045(9) 0.0019(9) C15 0.0178(11) 0.0145(10) 0.0114(11) -0.0063(9) 0.0008(8) -0.0021(8) C16 0.0170(11) 0.0136(10) 0.0128(11) -0.0061(9) 0.0002(8) -0.0022(8) C17 0.0211(11) 0.0154(11) 0.0163(12) -0.0041(9) -0.0016(9) -0.0024(9) C18 0.0262(12) 0.0160(11) 0.0198(12) -0.0055(10) 0.0047(10) -0.0077(9) C19 0.0165(11) 0.0197(11) 0.0232(13) -0.0108(10) 0.0027(9) -0.0059(9) C20 0.0146(11) 0.0176(11) 0.0205(12) -0.0082(10) -0.0015(9) -0.0017(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 O2 1.9329(15) . ? Cu1 O1 1.9469(16) . ? Cu1 N4 1.9595(18) . ? Cu1 N3 1.9721(18) . ? Cu1 O2 2.5239(16) 2_665 ? Cu1 Cu1 3.2239(5) 2_665 ? Cl1 O4 1.4256(17) . ? Cl1 O5 1.4347(18) . ? Cl1 O3 1.4453(17) . ? Cl1 O6 1.4651(17) . ? Cl2 O10 1.4340(18) . ? Cl2 O8 1.4357(19) . ? Cl2 O7 1.4407(18) . ? Cl2 O9 1.4605(17) . ? O1 C1 1.274(3) . ? O2 N1 1.366(2) . ? N1 C1 1.314(3) . ? N1 H1A 0.86(3) . ? N2 C5 1.339(3) . ? N2 C4 1.340(3) . ? N2 H2A 0.84(3) . ? N3 C11 1.343(3) . ? N3 C15 1.353(3) . ? N4 C20 1.345(3) . ? N4 C16 1.352(3) . ? C1 C2 1.486(3) . ? C2 C3 1.391(3) . ? C2 C6 1.394(3) . ? C3 C4 1.373(3) . ? C3 H3 0.9500 . ? C4 H4 0.9500 . ? C5 C6 1.374(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C11 C12 1.387(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.388(3) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.482(3) . ? C16 C17 1.384(3) . ? C17 C18 1.391(3) . ? C17 H17 0.9500 . ? C18 C19 1.381(3) . ? C18 H18 0.9500 . ? C19 C20 1.385(3) . ? C19 H19 0.9500 . ? C20 H20 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 O2 Cu1 O1 84.36(6) . . ? O2 Cu1 N4 174.18(7) . . ? O1 Cu1 N4 96.62(7) . . ? O2 Cu1 N3 97.56(7) . . ? O1 Cu1 N3 167.82(7) . . ? N4 Cu1 N3 82.70(7) . . ? O2 Cu1 O2 88.31(6) . 2_665 ? O1 Cu1 O2 100.66(6) . 2_665 ? N4 Cu1 O2 85.86(6) . 2_665 ? N3 Cu1 O2 91.43(6) . 2_665 ? O2 Cu1 Cu1 51.49(5) . 2_665 ? O1 Cu1 Cu1 94.93(5) . 2_665 ? N4 Cu1 Cu1 122.68(5) . 2_665 ? N3 Cu1 Cu1 95.64(5) . 2_665 ? O2 Cu1 Cu1 36.82(3) 2_665 2_665 ? O4 Cl1 O5 110.54(12) . . ? O4 Cl1 O3 110.99(11) . . ? O5 Cl1 O3 109.63(11) . . ? O4 Cl1 O6 109.46(11) . . ? O5 Cl1 O6 108.75(11) . . ? O3 Cl1 O6 107.38(10) . . ? O10 Cl2 O8 111.12(12) . . ? O10 Cl2 O7 109.70(12) . . ? O8 Cl2 O7 109.23(11) . . ? O10 Cl2 O9 108.87(11) . . ? O8 Cl2 O9 109.45(11) . . ? O7 Cl2 O9 108.41(11) . . ? C1 O1 Cu1 109.22(13) . . ? N1 O2 Cu1 106.96(12) . . ? C1 N1 O2 118.39(18) . . ? C1 N1 H1A 124(2) . . ? O2 N1 H1A 118(2) . . ? C5 N2 C4 122.8(2) . . ? C5 N2 H2A 119.9(18) . . ? C4 N2 H2A 117.3(18) . . ? C11 N3 C15 119.65(19) . . ? C11 N3 Cu1 126.57(15) . . ? C15 N3 Cu1 113.70(14) . . ? C20 N4 C16 119.58(19) . . ? C20 N4 Cu1 125.81(16) . . ? C16 N4 Cu1 114.54(14) . . ? O1 C1 N1 120.2(2) . . ? O1 C1 C2 120.16(19) . . ? N1 C1 C2 119.7(2) . . ? C3 C2 C6 119.5(2) . . ? C3 C2 C1 122.8(2) . . ? C6 C2 C1 117.7(2) . . ? C4 C3 C2 119.1(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? N2 C4 C3 119.7(2) . . ? N2 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N2 C5 C6 119.6(2) . . ? N2 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C2 119.1(2) . . ? C5 C6 H6 120.4 . . ? C2 C6 H6 120.4 . . ? N3 C11 C12 121.9(2) . . ? N3 C11 H11 119.0 . . ? C12 C11 H11 119.0 . . ? C13 C12 C11 118.4(2) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C14 120.0(2) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 118.8(2) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? N3 C15 C14 121.2(2) . . ? N3 C15 C16 114.50(19) . . ? C14 C15 C16 124.2(2) . . ? N4 C16 C17 121.6(2) . . ? N4 C16 C15 114.10(19) . . ? C17 C16 C15 124.3(2) . . ? C16 C17 C18 118.5(2) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? C19 C18 C17 119.8(2) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C20 118.8(2) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? N4 C20 C19 121.6(2) . . ? N4 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? 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 O9 0.86(3) 2.01(3) 2.869(3) 177(3) . N2 H2A O6 0.84(3) 1.96(3) 2.771(3) 163(3) 2_664 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.376 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 962652' ####################################################################### # # 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_n187ds _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 Cu N4 O2, Cl O4' _chemical_formula_sum 'C18 H13 Cl Cu N4 O6' _chemical_formula_weight 480.31 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.9852(3) _cell_length_b 24.5926(11) _cell_length_c 9.3471(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.870(3) _cell_angle_gamma 90.00 _cell_volume 1802.62(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5756 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.770 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 1.408 _exptl_absorpt_correction_type multi-scan' _exptl_absorpt_correction_T_min 0.7564 _exptl_absorpt_correction_T_max 0.8593 _exptl_absorpt_process_details 'SADABS v.2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24300 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.0461 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3928 _reflns_number_gt 3026 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Brandenburg, 2006)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0751P)^2^+5.6350P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3928 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1582 _refine_ls_wR_factor_gt 0.1444 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 0.12142(6) 0.12863(2) 0.92503(5) 0.02598(18) Uani 1 1 d . . . Cl2 Cl 0.54995(14) 0.13847(4) 0.47111(12) 0.0321(3) Uani 1 1 d . . . O1 O 0.0658(4) 0.15481(11) 0.7226(3) 0.0292(6) Uani 1 1 d . . . O2 O -0.0177(4) 0.18732(12) 0.9676(3) 0.0318(7) Uani 1 1 d . . . O3 O 0.6275(7) 0.16371(19) 0.6041(4) 0.0731(14) Uani 1 1 d . . . O4 O 0.3979(5) 0.16700(18) 0.4155(6) 0.0853(17) Uani 1 1 d . . . O5 O 0.6635(7) 0.1423(2) 0.3736(7) 0.103(2) Uani 1 1 d . . . O6 O 0.5047(6) 0.08345(15) 0.4929(5) 0.0630(11) Uani 1 1 d . . . N1 N 0.1162(4) 0.08999(14) 1.1123(4) 0.0294(8) Uani 1 1 d . . . N2 N 0.2305(4) 0.05964(14) 0.8769(4) 0.0284(8) Uani 1 1 d . . . N3 N 0.3519(4) 0.18413(15) 0.9656(4) 0.0327(8) Uani 1 1 d . . . N4 N -0.0354(4) 0.22047(14) 0.8490(4) 0.0310(8) Uani 1 1 d . . . H4N H -0.0556 0.2535 0.8637 0.046 Uiso 1 1 d R . . C1 C 0.0586(5) 0.1071(2) 1.2289(5) 0.0378(11) Uani 1 1 d . . . H1 H 0.0168 0.1432 1.2310 0.045 Uiso 1 1 calc R . . C2 C 0.0580(6) 0.0728(2) 1.3494(6) 0.0458(13) Uani 1 1 d . . . H2 H 0.0192 0.0860 1.4330 0.055 Uiso 1 1 calc R . . C3 C 0.1145(6) 0.0201(2) 1.3446(6) 0.0468(13) Uani 1 1 d . . . H3 H 0.1152 -0.0031 1.4259 0.056 Uiso 1 1 calc R . . C4 C 0.1705(6) 0.0004(2) 1.2223(6) 0.0407(12) Uani 1 1 d . . . C5 C 0.2265(6) -0.0544(2) 1.2026(7) 0.0527(16) Uani 1 1 d . . . H5 H 0.2234 -0.0804 1.2771 0.063 Uiso 1 1 calc R . . C6 C 0.2828(6) -0.0696(2) 1.0826(7) 0.0479(14) Uani 1 1 d . . . H6 H 0.3176 -0.1062 1.0735 0.057 Uiso 1 1 calc R . . C7 C 0.2916(5) -0.03205(19) 0.9681(6) 0.0397(11) Uani 1 1 d . . . C8 C 0.3569(6) -0.0440(2) 0.8419(6) 0.0443(13) Uani 1 1 d . . . H8 H 0.3998 -0.0793 0.8282 0.053 Uiso 1 1 calc R . . C9 C 0.3579(6) -0.0046(2) 0.7394(6) 0.0409(11) Uani 1 1 d . . . H9 H 0.4037 -0.0122 0.6548 0.049 Uiso 1 1 calc R . . C10 C 0.2917(5) 0.04698(18) 0.7585(5) 0.0335(10) Uani 1 1 d . . . H10 H 0.2904 0.0737 0.6848 0.040 Uiso 1 1 calc R . . C11 C 0.2321(5) 0.02161(17) 0.9812(5) 0.0299(9) Uani 1 1 d . . . C12 C 0.1719(5) 0.03762(17) 1.1088(5) 0.0301(9) Uani 1 1 d . . . C13 C 0.4356(5) 0.19618(19) 0.8588(5) 0.0355(10) Uani 1 1 d . . . H13 H 0.4217 0.1732 0.7757 0.043 Uiso 1 1 calc R . . C14 C 0.3745(5) 0.21643(18) 1.0817(5) 0.0309(9) Uani 1 1 d . . . H14 H 0.3152 0.2082 1.1581 0.037 Uiso 1 1 calc R . . C15 C 0.0041(5) 0.20280(17) 0.7275(5) 0.0284(9) Uani 1 1 d . . . C16 C -0.0192(5) 0.23833(17) 0.5969(5) 0.0283(9) Uani 1 1 d . . . C17 C 0.0661(6) 0.2261(2) 0.4853(6) 0.0414(11) Uani 1 1 d . . . H17 H 0.1398 0.1955 0.4920 0.050 Uiso 1 1 calc R . . C18 C 0.0423(6) 0.2589(2) 0.3650(6) 0.0427(12) Uani 1 1 d . . . H18 H 0.0982 0.2511 0.2863 0.051 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 0.0244(3) 0.0211(3) 0.0340(3) 0.0014(2) 0.0093(2) 0.00045(19) Cl2 0.0345(5) 0.0309(6) 0.0326(6) -0.0010(4) 0.0109(4) -0.0005(4) O1 0.0310(15) 0.0229(15) 0.0359(16) 0.0013(12) 0.0123(12) 0.0038(12) O2 0.0352(16) 0.0270(15) 0.0360(17) 0.0033(13) 0.0144(13) 0.0066(12) O3 0.111(4) 0.064(3) 0.045(2) -0.019(2) 0.015(2) -0.030(3) O4 0.050(2) 0.053(3) 0.136(5) 0.040(3) -0.026(3) -0.014(2) O5 0.085(3) 0.120(4) 0.128(5) -0.077(4) 0.080(3) -0.051(3) O6 0.087(3) 0.031(2) 0.066(3) 0.0029(18) 0.000(2) -0.0093(19) N1 0.0231(16) 0.0288(18) 0.036(2) 0.0043(15) 0.0052(14) -0.0059(14) N2 0.0194(16) 0.0253(18) 0.039(2) -0.0028(15) 0.0012(14) -0.0030(13) N3 0.0266(18) 0.0300(19) 0.044(2) -0.0054(16) 0.0121(16) -0.0046(15) N4 0.0324(18) 0.0238(18) 0.039(2) 0.0006(15) 0.0117(16) 0.0051(14) C1 0.026(2) 0.046(3) 0.042(3) -0.002(2) 0.0077(19) -0.009(2) C2 0.031(2) 0.068(4) 0.038(3) 0.006(2) 0.005(2) -0.016(2) C3 0.032(2) 0.060(3) 0.045(3) 0.023(3) -0.002(2) -0.016(2) C4 0.024(2) 0.042(3) 0.050(3) 0.018(2) -0.007(2) -0.0103(19) C5 0.035(3) 0.037(3) 0.074(4) 0.028(3) -0.021(3) -0.013(2) C6 0.035(3) 0.028(2) 0.071(4) 0.005(2) -0.013(3) -0.003(2) C7 0.024(2) 0.027(2) 0.061(3) -0.002(2) -0.010(2) -0.0025(17) C8 0.030(2) 0.027(2) 0.068(4) -0.016(2) -0.010(2) 0.0024(19) C9 0.029(2) 0.037(3) 0.054(3) -0.018(2) 0.002(2) 0.0008(19) C10 0.025(2) 0.031(2) 0.043(3) -0.0084(19) 0.0011(18) -0.0012(17) C11 0.0169(17) 0.025(2) 0.044(3) 0.0017(18) -0.0030(16) -0.0042(15) C12 0.0199(18) 0.026(2) 0.041(2) 0.0065(18) -0.0030(17) -0.0072(16) C13 0.028(2) 0.035(2) 0.046(3) -0.009(2) 0.0151(19) -0.0039(18) C14 0.028(2) 0.030(2) 0.038(2) -0.0034(18) 0.0128(18) -0.0030(17) C15 0.0253(19) 0.023(2) 0.037(2) 0.0041(17) 0.0079(17) 0.0001(16) C16 0.0219(19) 0.026(2) 0.038(2) 0.0036(18) 0.0084(17) 0.0007(16) C17 0.043(3) 0.033(2) 0.052(3) 0.006(2) 0.021(2) 0.013(2) C18 0.044(3) 0.044(3) 0.046(3) 0.010(2) 0.026(2) 0.014(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 O2 1.908(3) . yes Cu1 O1 1.969(3) . yes Cu1 N2 1.997(3) . yes Cu1 N1 1.999(4) . yes Cu1 N3 2.265(4) . yes Cl2 O5 1.405(5) . ? Cl2 O4 1.414(4) . ? Cl2 O3 1.423(4) . ? Cl2 O6 1.425(4) . ? O1 C15 1.283(5) . ? O2 N4 1.361(5) . ? N1 C1 1.329(6) . ? N1 C12 1.365(6) . ? N2 C10 1.328(6) . ? N2 C11 1.349(6) . ? N3 C14 1.329(6) . ? N3 C13 1.335(6) . ? N4 C15 1.309(5) . ? N4 H4N 0.8440 . ? C1 C2 1.406(7) . ? C1 H1 0.9500 . ? C2 C3 1.376(8) . ? C2 H2 0.9500 . ? C3 C4 1.391(8) . ? C3 H3 0.9500 . ? C4 C12 1.402(6) . ? C4 C5 1.442(8) . ? C5 C6 1.338(9) . ? C5 H5 0.9500 . ? C6 C7 1.426(8) . ? C6 H6 0.9500 . ? C7 C8 1.408(8) . ? C7 C11 1.415(6) . ? C8 C9 1.364(8) . ? C8 H8 0.9500 . ? C9 C10 1.399(6) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.424(6) . ? C13 C18 1.389(6) 4_666 ? C13 H13 0.9500 . ? C14 C16 1.390(6) 4_666 ? C14 H14 0.9500 . ? C15 C16 1.484(6) . ? C16 C17 1.382(6) . ? C16 C14 1.390(6) 4_565 ? C17 C18 1.368(7) . ? C17 H17 0.9500 . ? C18 C13 1.389(6) 4_565 ? C18 H18 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 O2 Cu1 O1 85.30(12) . . yes O2 Cu1 N2 170.18(13) . . ? O1 Cu1 N2 95.18(13) . . ? O2 Cu1 N1 93.91(14) . . ? O1 Cu1 N1 163.51(13) . . ? N2 Cu1 N1 82.84(15) . . yes O2 Cu1 N3 89.76(13) . . ? O1 Cu1 N3 89.60(13) . . ? N2 Cu1 N3 100.05(13) . . yes N1 Cu1 N3 106.88(14) . . yes O5 Cl2 O4 110.1(4) . . ? O5 Cl2 O3 108.1(3) . . ? O4 Cl2 O3 107.9(3) . . ? O5 Cl2 O6 111.6(3) . . ? O4 Cl2 O6 107.5(3) . . ? O3 Cl2 O6 111.7(3) . . ? C15 O1 Cu1 106.6(3) . . ? N4 O2 Cu1 105.0(2) . . ? C1 N1 C12 118.8(4) . . ? C1 N1 Cu1 129.5(3) . . ? C12 N1 Cu1 111.6(3) . . ? C10 N2 C11 119.0(4) . . ? C10 N2 Cu1 129.2(3) . . ? C11 N2 Cu1 111.8(3) . . ? C14 N3 C13 117.9(4) . . ? C14 N3 Cu1 118.5(3) . . ? C13 N3 Cu1 120.9(3) . . ? C15 N4 O2 120.1(3) . . yes C15 N4 H4N 123.0 . . ? O2 N4 H4N 116.0 . . ? N1 C1 C2 121.5(5) . . ? N1 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C3 C2 C1 119.1(5) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.9(5) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C3 C4 C12 116.4(5) . . ? C3 C4 C5 125.9(5) . . ? C12 C4 C5 117.8(5) . . ? C6 C5 C4 122.1(5) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 121.2(5) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C8 C7 C11 116.8(5) . . ? C8 C7 C6 124.9(5) . . ? C11 C7 C6 118.4(5) . . ? C9 C8 C7 119.5(4) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C10 120.2(5) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? N2 C10 C9 121.7(5) . . ? N2 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? N2 C11 C7 122.8(4) . . ? N2 C11 C12 117.1(4) . . ? C7 C11 C12 120.1(4) . . ? N1 C12 C4 123.3(4) . . ? N1 C12 C11 116.3(4) . . ? C4 C12 C11 120.4(4) . . ? N3 C13 C18 122.3(4) . 4_666 ? N3 C13 H13 118.8 . . ? C18 C13 H13 118.8 4_666 . ? N3 C14 C16 123.2(4) . 4_666 ? N3 C14 H14 118.4 . . ? C16 C14 H14 118.4 4_666 . ? O1 C15 N4 119.5(4) . . yes O1 C15 C16 120.1(4) . . ? N4 C15 C16 120.3(4) . . ? C17 C16 C14 118.3(4) . 4_565 ? C17 C16 C15 119.3(4) . . ? C14 C16 C15 122.3(4) 4_565 . ? C18 C17 C16 118.7(4) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C17 C18 C13 119.5(4) . 4_565 ? C17 C18 H18 120.3 . . ? C13 C18 H18 120.3 4_565 . ? 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 _geom_hbond_publ_flag N4 H4N O4 0.84 2.06 2.907(5) 175.8 4_566 yes _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.467 _refine_diff_density_min -0.961 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 962653' ####################################################################### # # 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_ig300d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '4(C16 H13 Cu N4 O2), 13(H2 O), 4(H O)' _chemical_formula_sum 'C64 H82 Cu4 N16 O25' _chemical_formula_weight 1729.62 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.4187(6) _cell_length_b 12.5647(6) _cell_length_c 21.7018(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.669(3) _cell_angle_gamma 90.00 _cell_volume 3595.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11802 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1788 _exptl_absorpt_coefficient_mu 1.259 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8014 _exptl_absorpt_correction_T_max 0.9620 _exptl_absorpt_process_details 'Xprep in Shelxtl v.6.14-1 (Sheldrick, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34020 _diffrn_reflns_av_R_equivalents 0.0892 _diffrn_reflns_av_sigmaI/netI 0.0764 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 26.00 _reflns_number_total 7061 _reflns_number_gt 4418 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Brandenburg, 2006)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0350P)^2^+8.8279P] 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 7061 _refine_ls_number_parameters 496 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1060 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.07921(4) 0.73370(4) 0.11338(2) 0.01918(15) Uani 1 1 d . . . Cu1B Cu 0.40858(4) 0.72107(4) 0.38342(2) 0.01953(16) Uani 1 1 d . . . O1 O -0.0631(2) 0.6994(3) 0.09476(13) 0.0241(7) Uani 1 1 d . . . O2 O 0.0857(2) 0.6215(2) 0.17536(14) 0.0230(7) Uani 1 1 d . . . O3 O 0.4138(3) 0.4431(3) 0.49235(17) 0.0555(12) Uani 1 1 d . . . H3O H 0.4239 0.4033 0.5255 0.083 Uiso 1 1 d R . . H3P H 0.4698 0.4805 0.4968 0.083 Uiso 0.50 1 d PR . . H3C H 0.3919 0.4141 0.4570 0.083 Uiso 0.50 1 d PR . . O4 O 0.3071(3) 0.4297(3) 0.37129(17) 0.0391(9) Uani 1 1 d . . . H4O H 0.3407 0.4332 0.4090 0.059 Uiso 0.50 1 d PR . . H4P H 0.3308 0.4823 0.3535 0.059 Uiso 1 1 d R . . H4A H 0.2491 0.4526 0.3754 0.059 Uiso 0.50 1 d PR . . O5 O 0.1950(3) 0.4536(3) 0.12827(16) 0.0361(9) Uani 1 1 d . . . H5O H 0.1690 0.5108 0.1427 0.054 Uiso 1 1 d R . . O6 O 0.0816(3) 0.4382(3) 0.00880(17) 0.0462(10) Uani 1 1 d . . . H6O H 0.1312 0.4506 0.0399 0.069 Uiso 1 1 d R . . H6P H 0.1045 0.3908 -0.0135 0.069 Uiso 1 1 d R . . O7 O 0.2272(2) 0.1216(3) 0.09953(16) 0.0372(9) Uani 1 1 d . . . H7O H 0.2260 0.1474 0.0628 0.056 Uiso 1 1 d R . . O8 O 0.1897(3) 0.2638(3) 0.19125(17) 0.0449(10) Uani 1 1 d . . . H8O H 0.1917 0.3233 0.1720 0.067 Uiso 1 1 d R . . H8P H 0.2015 0.2115 0.1683 0.067 Uiso 1 1 d R . . O9 O 0.2774(3) 0.2308(4) 0.31646(19) 0.0666(14) Uani 1 1 d . . . H9O H 0.2486 0.2409 0.2782 0.100 Uiso 1 1 d R . . H9P H 0.2740 0.2925 0.3331 0.100 Uiso 1 1 d R . . O10 O 0.2352(3) 0.2817(4) 0.47673(19) 0.0548(12) Uani 1 1 d . . . H10D H 0.1808 0.2566 0.4566 0.082 Uiso 1 1 d R . . H10E H 0.2563 0.3289 0.4549 0.082 Uiso 1 1 d R . . O11 O -0.2784(11) 0.6041(14) 0.1041(9) 0.165(7) Uani 0.50 1 d P . . H11D H -0.2894 0.5379 0.0984 0.248 Uiso 0.50 1 d PR . . H11A H -0.2950 0.6360 0.0676 0.248 Uiso 0.50 1 d PR . . N1 N 0.2292(3) 0.7543(3) 0.12465(16) 0.0199(8) Uani 1 1 d . . . N2 N 0.0834(3) 0.8198(3) 0.03618(16) 0.0198(8) Uani 1 1 d . . . N3 N 0.0543(3) 0.8752(3) 0.17828(16) 0.0194(8) Uani 1 1 d . . . N4 N -0.0889(3) 0.6331(3) 0.14175(17) 0.0244(9) Uani 1 1 d . . . H4N H -0.1515 0.6176 0.1452 0.029 Uiso 1 1 calc R . . C1 C 0.3000(3) 0.7151(4) 0.1717(2) 0.0225(10) Uani 1 1 d . . . H1 H 0.2790 0.6683 0.2012 0.027 Uiso 1 1 calc R . . C2 C 0.4014(3) 0.7401(4) 0.1785(2) 0.0230(10) Uani 1 1 d . . . H2 H 0.4496 0.7111 0.2118 0.028 Uiso 1 1 calc R . . C3 C 0.4315(4) 0.8092(4) 0.1350(2) 0.0234(10) Uani 1 1 d . . . H3 H 0.5008 0.8282 0.1385 0.028 Uiso 1 1 calc R . . C4 C 0.3602(3) 0.8495(4) 0.0874(2) 0.0221(10) Uani 1 1 d . . . H4 H 0.3797 0.8970 0.0576 0.027 Uiso 1 1 calc R . . C5 C 0.2590(3) 0.8205(4) 0.0828(2) 0.0193(10) Uani 1 1 d . . . C6 C 0.1767(3) 0.8571(4) 0.03232(19) 0.0190(10) Uani 1 1 d . . . C7 C 0.1922(4) 0.9231(4) -0.0166(2) 0.0236(11) Uani 1 1 d . . . H7 H 0.2577 0.9501 -0.0183 0.028 Uiso 1 1 calc R . . C8 C 0.1095(4) 0.9485(4) -0.0627(2) 0.0248(11) Uani 1 1 d . . . H8 H 0.1185 0.9919 -0.0971 0.030 Uiso 1 1 calc R . . C9 C 0.0140(4) 0.9107(4) -0.0588(2) 0.0255(11) Uani 1 1 d . . . H9 H -0.0433 0.9282 -0.0899 0.031 Uiso 1 1 calc R . . C10 C 0.0045(4) 0.8468(4) -0.0084(2) 0.0225(10) Uani 1 1 d . . . H10 H -0.0609 0.8208 -0.0052 0.027 Uiso 1 1 calc R . . C11 C -0.0351(3) 0.8868(4) 0.1948(2) 0.0204(10) Uani 1 1 d . . . H11 H -0.0894 0.8428 0.1752 0.024 Uiso 1 1 calc R . . C12 C -0.0539(3) 0.9600(4) 0.23947(19) 0.0203(10) Uani 1 1 d . . . H12 H -0.1198 0.9664 0.2491 0.024 Uiso 1 1 calc R . . C13 C 0.0245(4) 1.0235(4) 0.2697(2) 0.0203(10) Uani 1 1 d . . . C14 C 0.1185(3) 1.0128(4) 0.2516(2) 0.0232(11) Uani 1 1 d . . . H14 H 0.1746 1.0551 0.2706 0.028 Uiso 1 1 calc R . . C15 C 0.1286(4) 0.9401(4) 0.2058(2) 0.0233(11) Uani 1 1 d . . . H15 H 0.1923 0.9355 0.1929 0.028 Uiso 1 1 calc R . . C16 C -0.0088(4) 0.5974(4) 0.1795(2) 0.0215(10) Uani 1 1 d . . . O1B O 0.5444(2) 0.6746(2) 0.40365(13) 0.0222(7) Uani 1 1 d . . . O2B O 0.3935(2) 0.6094(2) 0.31882(13) 0.0200(7) Uani 1 1 d . . . N1B N 0.2620(3) 0.7564(3) 0.37390(16) 0.0213(8) Uani 1 1 d . . . N2B N 0.4158(3) 0.8100(3) 0.46088(16) 0.0227(9) Uani 1 1 d . . . N3B N 0.4523(3) 0.8614(3) 0.32454(16) 0.0224(9) Uani 1 1 d . . . N4B N 0.5663(3) 0.6071(3) 0.35629(17) 0.0228(9) Uani 1 1 d . . . H4M H 0.6280 0.5854 0.3543 0.027 Uiso 1 1 calc R . . C1B C 0.1879(3) 0.7226(4) 0.3287(2) 0.0235(10) Uani 1 1 d . . . H1B H 0.2048 0.6767 0.2974 0.028 Uiso 1 1 calc R . . C2B C 0.0873(4) 0.7512(4) 0.3251(2) 0.0267(11) Uani 1 1 d . . . H2B H 0.0362 0.7251 0.2923 0.032 Uiso 1 1 calc R . . C3B C 0.0633(4) 0.8188(4) 0.3706(2) 0.0303(12) Uani 1 1 d . . . H3B H -0.0050 0.8397 0.3696 0.036 Uiso 1 1 calc R . . C4B C 0.1402(4) 0.8557(4) 0.4178(2) 0.0289(12) Uani 1 1 d . . . H4B H 0.1253 0.9034 0.4489 0.035 Uiso 1 1 calc R . . C5B C 0.2388(3) 0.8219(4) 0.41886(19) 0.0204(10) Uani 1 1 d . . . C6B C 0.3263(4) 0.8530(4) 0.4676(2) 0.0244(11) Uani 1 1 d . . . C7B C 0.3200(4) 0.9203(4) 0.5178(2) 0.0330(13) Uani 1 1 d . . . H7B H 0.2569 0.9507 0.5221 0.040 Uiso 1 1 calc R . . C8B C 0.4068(5) 0.9424(4) 0.5613(2) 0.0379(14) Uani 1 1 d . . . H8B H 0.4036 0.9877 0.5959 0.045 Uiso 1 1 calc R . . C9B C 0.4970(4) 0.8983(4) 0.5539(2) 0.0361(13) Uani 1 1 d . . . H9B H 0.5572 0.9123 0.5834 0.043 Uiso 1 1 calc R . . C10B C 0.4994(4) 0.8319(4) 0.5022(2) 0.0295(12) Uani 1 1 d . . . H10B H 0.5622 0.8021 0.4966 0.035 Uiso 1 1 calc R . . C11B C 0.5438(3) 0.8676(4) 0.3087(2) 0.0224(10) Uani 1 1 d . . . H11B H 0.5949 0.8197 0.3281 0.027 Uiso 1 1 calc R . . C12B C 0.5685(3) 0.9394(4) 0.2659(2) 0.0222(10) Uani 1 1 d . . . H12B H 0.6356 0.9423 0.2579 0.027 Uiso 1 1 calc R . . C13B C 0.4941(3) 1.0075(4) 0.23463(19) 0.0208(10) Uani 1 1 d . . . C14B C 0.3994(3) 1.0044(4) 0.2525(2) 0.0235(11) Uani 1 1 d . . . H14B H 0.3475 1.0526 0.2345 0.028 Uiso 1 1 calc R . . C15B C 0.3815(4) 0.9308(4) 0.2966(2) 0.0251(11) Uani 1 1 d . . . H15B H 0.3162 0.9290 0.3076 0.030 Uiso 1 1 calc R . . C16B C 0.4873(3) 0.5799(4) 0.3161(2) 0.0199(10) 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 0.0251(3) 0.0183(3) 0.0154(3) 0.0013(2) 0.0068(2) -0.0003(2) Cu1B 0.0229(3) 0.0206(3) 0.0158(3) -0.0018(2) 0.0054(2) 0.0006(2) O1 0.0332(18) 0.0232(19) 0.0151(16) 0.0065(13) 0.0028(13) -0.0050(14) O2 0.0277(18) 0.0219(19) 0.0208(17) 0.0022(13) 0.0082(13) 0.0020(14) O3 0.068(3) 0.071(3) 0.032(2) 0.025(2) 0.022(2) 0.036(2) O4 0.040(2) 0.039(2) 0.042(2) -0.0036(17) 0.0162(17) -0.0121(18) O5 0.033(2) 0.035(2) 0.042(2) -0.0075(17) 0.0106(16) 0.0047(16) O6 0.065(3) 0.043(3) 0.031(2) -0.0145(18) 0.0104(19) -0.007(2) O7 0.0266(19) 0.052(3) 0.033(2) -0.0008(17) 0.0048(15) -0.0013(17) O8 0.057(2) 0.041(2) 0.037(2) 0.0017(18) 0.0094(18) 0.001(2) O9 0.090(3) 0.055(3) 0.044(3) -0.021(2) -0.017(2) 0.025(3) O10 0.036(2) 0.070(3) 0.060(3) -0.023(2) 0.0119(19) -0.016(2) O11 0.116(12) 0.134(15) 0.23(2) -0.046(13) 0.001(12) -0.015(11) N1 0.026(2) 0.019(2) 0.0147(18) 0.0008(16) 0.0048(15) 0.0018(17) N2 0.026(2) 0.018(2) 0.017(2) -0.0021(15) 0.0077(16) 0.0000(17) N3 0.025(2) 0.018(2) 0.0158(19) -0.0024(15) 0.0046(16) -0.0004(16) N4 0.026(2) 0.028(2) 0.021(2) 0.0043(17) 0.0075(17) -0.0090(18) C1 0.033(3) 0.022(3) 0.016(2) -0.0001(18) 0.0109(19) 0.004(2) C2 0.022(2) 0.026(3) 0.020(2) -0.002(2) 0.0012(18) 0.002(2) C3 0.025(2) 0.023(3) 0.022(2) -0.008(2) 0.0049(19) -0.003(2) C4 0.030(3) 0.019(3) 0.018(2) 0.0005(18) 0.0070(19) -0.004(2) C5 0.026(2) 0.015(3) 0.018(2) -0.0005(18) 0.0059(19) 0.0009(19) C6 0.027(2) 0.017(3) 0.015(2) -0.0025(18) 0.0072(19) -0.001(2) C7 0.024(3) 0.027(3) 0.021(2) 0.002(2) 0.009(2) 0.002(2) C8 0.034(3) 0.022(3) 0.020(2) 0.0036(19) 0.009(2) 0.000(2) C9 0.030(3) 0.025(3) 0.020(2) 0.000(2) 0.003(2) 0.005(2) C10 0.027(2) 0.020(3) 0.022(2) -0.0024(19) 0.0066(19) -0.003(2) C11 0.021(2) 0.023(3) 0.017(2) 0.0009(19) 0.0048(18) 0.002(2) C12 0.021(2) 0.025(3) 0.016(2) 0.0000(19) 0.0050(18) 0.005(2) C13 0.031(3) 0.016(3) 0.014(2) -0.0021(18) 0.0057(19) 0.004(2) C14 0.025(3) 0.021(3) 0.024(3) -0.0032(19) 0.005(2) -0.003(2) C15 0.026(3) 0.023(3) 0.022(3) -0.004(2) 0.009(2) -0.001(2) C16 0.031(3) 0.016(3) 0.017(2) -0.0013(18) 0.005(2) 0.000(2) O1B 0.0269(17) 0.0243(19) 0.0145(16) -0.0042(13) 0.0012(13) 0.0015(14) O2B 0.0182(16) 0.0228(19) 0.0197(16) -0.0028(13) 0.0056(12) 0.0043(13) N1B 0.027(2) 0.020(2) 0.0194(19) 0.0020(16) 0.0097(16) -0.0006(17) N2B 0.032(2) 0.019(2) 0.017(2) 0.0012(16) 0.0055(17) -0.0025(18) N3B 0.028(2) 0.022(2) 0.018(2) -0.0011(16) 0.0053(17) -0.0020(18) N4B 0.021(2) 0.028(2) 0.021(2) -0.0025(17) 0.0069(16) 0.0063(17) C1B 0.030(3) 0.023(3) 0.019(2) 0.0030(19) 0.0083(19) 0.003(2) C2B 0.027(2) 0.026(3) 0.027(3) 0.008(2) 0.005(2) 0.000(2) C3B 0.030(3) 0.024(3) 0.041(3) 0.011(2) 0.015(2) 0.009(2) C4B 0.039(3) 0.023(3) 0.031(3) 0.007(2) 0.022(2) 0.008(2) C5B 0.031(3) 0.016(3) 0.017(2) 0.0032(18) 0.0096(19) 0.001(2) C6B 0.039(3) 0.016(3) 0.021(2) 0.0010(19) 0.011(2) -0.004(2) C7B 0.054(4) 0.022(3) 0.029(3) -0.003(2) 0.024(3) -0.002(3) C8B 0.069(4) 0.026(3) 0.021(3) -0.009(2) 0.014(3) -0.014(3) C9B 0.054(4) 0.034(3) 0.020(3) -0.003(2) 0.005(2) -0.019(3) C10B 0.038(3) 0.028(3) 0.022(3) 0.004(2) 0.006(2) -0.011(2) C11B 0.024(2) 0.024(3) 0.019(2) -0.0016(19) 0.0016(19) 0.002(2) C12B 0.019(2) 0.025(3) 0.023(2) -0.001(2) 0.0049(19) -0.002(2) C13B 0.028(3) 0.022(3) 0.013(2) -0.0044(18) 0.0051(19) -0.003(2) C14B 0.023(2) 0.025(3) 0.024(3) 0.003(2) 0.0067(19) 0.001(2) C15B 0.026(3) 0.023(3) 0.028(3) 0.000(2) 0.010(2) -0.003(2) C16B 0.028(3) 0.017(3) 0.015(2) 0.0030(18) 0.0033(19) 0.004(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 O1 1.926(3) . ? Cu1 O2 1.939(3) . ? Cu1 N1 1.999(4) . ? Cu1 N2 2.004(4) . ? Cu1 N3 2.330(4) . ? Cu1B O1B 1.887(3) . ? Cu1B O2B 1.967(3) . ? Cu1B N1B 1.990(4) . ? Cu1B N2B 2.006(4) . ? Cu1B N3B 2.316(4) . ? O1 N4 1.408(4) . ? O2 C16 1.324(5) . ? O3 H3O 0.8650 . ? O3 H3P 0.8764 . ? O3 H3C 0.8501 . ? O4 H4O 0.8596 . ? O4 H4P 0.8560 . ? O4 H4A 0.8500 . ? O5 H5O 0.8808 . ? O6 H6O 0.8703 . ? O6 H6P 0.8591 . ? O7 H7O 0.8573 . ? O8 H8O 0.8592 . ? O8 H8P 0.8565 . ? O9 H9O 0.8587 . ? O9 H9P 0.8599 . ? O10 H10D 0.8400 . ? O10 H10E 0.8400 . ? O11 H11D 0.8500 . ? O11 H11A 0.8787 . ? N1 C5 1.347(6) . ? N1 C1 1.352(6) . ? N2 C10 1.339(6) . ? N2 C6 1.354(6) . ? N3 C11 1.323(6) . ? N3 C15 1.339(6) . ? N4 C16 1.304(6) . ? N4 H4N 0.8800 . ? C1 C2 1.377(6) . ? C1 H1 0.9500 . ? C2 C3 1.395(6) . ? C2 H2 0.9500 . ? C3 C4 1.369(6) . ? C3 H3 0.9500 . ? C4 C5 1.391(6) . ? C4 H4 0.9500 . ? C5 C6 1.477(6) . ? C6 C7 1.392(6) . ? C7 C8 1.387(6) . ? C7 H7 0.9500 . ? C8 C9 1.384(7) . ? C8 H8 0.9500 . ? C9 C10 1.382(6) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.393(6) . ? C11 H11 0.9500 . ? C12 C13 1.385(6) . ? C12 H12 0.9500 . ? C13 C14 1.395(6) . ? C13 C16 1.486(6) 2 ? C14 C15 1.375(6) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C13 1.486(6) 2_545 ? O1B N4B 1.405(5) . ? O2B C16B 1.324(5) . ? N1B C1B 1.330(6) . ? N1B C5B 1.355(6) . ? N2B C10B 1.329(6) . ? N2B C6B 1.348(6) . ? N3B C11B 1.338(6) . ? N3B C15B 1.349(6) . ? N4B C16B 1.289(6) . ? N4B H4M 0.8800 . ? C1B C2B 1.385(6) . ? C1B H1B 0.9500 . ? C2B C3B 1.385(7) . ? C2B H2B 0.9500 . ? C3B C4B 1.393(7) . ? C3B H3B 0.9500 . ? C4B C5B 1.386(7) . ? C4B H4B 0.9500 . ? C5B C6B 1.479(6) . ? C6B C7B 1.394(6) . ? C7B C8B 1.384(8) . ? C7B H7B 0.9500 . ? C8B C9B 1.367(8) . ? C8B H8B 0.9500 . ? C9B C10B 1.403(7) . ? C9B H9B 0.9500 . ? C10B H10B 0.9500 . ? C11B C12B 1.377(6) . ? C11B H11B 0.9500 . ? C12B C13B 1.393(6) . ? C12B H12B 0.9500 . ? C13B C14B 1.396(6) . ? C13B C16B 1.484(6) 2_655 ? C14B C15B 1.383(6) . ? C14B H14B 0.9500 . ? C15B H15B 0.9500 . ? C16B C13B 1.484(6) 2_645 ? 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 O1 Cu1 O2 84.17(13) . . ? O1 Cu1 N1 172.46(14) . . ? O2 Cu1 N1 95.40(14) . . ? O1 Cu1 N2 97.23(14) . . ? O2 Cu1 N2 165.39(14) . . ? N1 Cu1 N2 81.30(15) . . ? O1 Cu1 N3 92.89(13) . . ? O2 Cu1 N3 97.39(13) . . ? N1 Cu1 N3 94.63(14) . . ? N2 Cu1 N3 97.06(14) . . ? O1B Cu1B O2B 84.98(12) . . ? O1B Cu1B N1B 170.82(14) . . ? O2B Cu1B N1B 96.66(14) . . ? O1B Cu1B N2B 94.76(14) . . ? O2B Cu1B N2B 167.73(14) . . ? N1B Cu1B N2B 81.71(16) . . ? O1B Cu1B N3B 91.81(14) . . ? O2B Cu1B N3B 98.81(13) . . ? N1B Cu1B N3B 96.85(14) . . ? N2B Cu1B N3B 93.46(14) . . ? N4 O1 Cu1 110.3(2) . . ? C16 O2 Cu1 107.0(3) . . ? H3O O3 H3P 102.6 . . ? H3O O3 H3C 118.4 . . ? H3P O3 H3C 118.4 . . ? H4O O4 H4P 102.5 . . ? H4O O4 H4A 102.1 . . ? H4P O4 H4A 102.1 . . ? H6O O6 H6P 105.1 . . ? H8O O8 H8P 111.0 . . ? H9O O9 H9P 102.9 . . ? H10D O10 H10E 108.9 . . ? H11D O11 H11A 107.9 . . ? C5 N1 C1 118.7(4) . . ? C5 N1 Cu1 114.6(3) . . ? C1 N1 Cu1 126.6(3) . . ? C10 N2 C6 119.0(4) . . ? C10 N2 Cu1 126.9(3) . . ? C6 N2 Cu1 114.1(3) . . ? C11 N3 C15 116.7(4) . . ? C11 N3 Cu1 119.1(3) . . ? C15 N3 Cu1 123.8(3) . . ? C16 N4 O1 112.0(4) . . ? C16 N4 H4N 124.0 . . ? O1 N4 H4N 124.0 . . ? N1 C1 C2 122.6(4) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 118.3(4) . . ? C1 C2 H2 120.9 . . ? C3 C2 H2 120.9 . . ? C4 C3 C2 119.5(4) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 119.5(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 121.4(4) . . ? N1 C5 C6 114.7(4) . . ? C4 C5 C6 123.9(4) . . ? N2 C6 C7 121.6(4) . . ? N2 C6 C5 114.8(4) . . ? C7 C6 C5 123.6(4) . . ? C8 C7 C6 118.4(4) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C9 C8 C7 120.2(4) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 118.0(4) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? N2 C10 C9 122.9(4) . . ? N2 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? N3 C11 C12 123.5(4) . . ? N3 C11 H11 118.3 . . ? C12 C11 H11 118.3 . . ? C13 C12 C11 119.4(4) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 117.3(4) . . ? C12 C13 C16 120.8(4) . 2 ? C14 C13 C16 121.9(4) . 2 ? C15 C14 C13 118.8(4) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? N3 C15 C14 124.3(4) . . ? N3 C15 H15 117.9 . . ? C14 C15 H15 117.9 . . ? N4 C16 O2 124.5(4) . . ? N4 C16 C13 117.9(4) . 2_545 ? O2 C16 C13 117.6(4) . 2_545 ? N4B O1B Cu1B 109.9(2) . . ? C16B O2B Cu1B 105.0(3) . . ? C1B N1B C5B 119.0(4) . . ? C1B N1B Cu1B 126.5(3) . . ? C5B N1B Cu1B 114.5(3) . . ? C10B N2B C6B 120.1(4) . . ? C10B N2B Cu1B 125.7(3) . . ? C6B N2B Cu1B 114.1(3) . . ? C11B N3B C15B 116.8(4) . . ? C11B N3B Cu1B 121.6(3) . . ? C15B N3B Cu1B 120.7(3) . . ? C16B N4B O1B 113.5(4) . . ? C16B N4B H4M 123.3 . . ? O1B N4B H4M 123.3 . . ? N1B C1B C2B 123.1(4) . . ? N1B C1B H1B 118.4 . . ? C2B C1B H1B 118.4 . . ? C1B C2B C3B 118.1(5) . . ? C1B C2B H2B 121.0 . . ? C3B C2B H2B 121.0 . . ? C2B C3B C4B 119.4(5) . . ? C2B C3B H3B 120.3 . . ? C4B C3B H3B 120.3 . . ? C5B C4B C3B 119.0(5) . . ? C5B C4B H4B 120.5 . . ? C3B C4B H4B 120.5 . . ? N1B C5B C4B 121.3(4) . . ? N1B C5B C6B 114.7(4) . . ? C4B C5B C6B 124.0(4) . . ? N2B C6B C7B 120.7(5) . . ? N2B C6B C5B 114.9(4) . . ? C7B C6B C5B 124.4(5) . . ? C8B C7B C6B 119.3(5) . . ? C8B C7B H7B 120.3 . . ? C6B C7B H7B 120.3 . . ? C9B C8B C7B 119.4(5) . . ? C9B C8B H8B 120.3 . . ? C7B C8B H8B 120.3 . . ? C8B C9B C10B 119.1(5) . . ? C8B C9B H9B 120.5 . . ? C10B C9B H9B 120.5 . . ? N2B C10B C9B 121.4(5) . . ? N2B C10B H10B 119.3 . . ? C9B C10B H10B 119.3 . . ? N3B C11B C12B 123.9(4) . . ? N3B C11B H11B 118.0 . . ? C12B C11B H11B 118.0 . . ? C11B C12B C13B 119.4(4) . . ? C11B C12B H12B 120.3 . . ? C13B C12B H12B 120.3 . . ? C12B C13B C14B 117.0(4) . . ? C12B C13B C16B 122.3(4) . 2_655 ? C14B C13B C16B 120.7(4) . 2_655 ? C15B C14B C13B 119.6(4) . . ? C15B C14B H14B 120.2 . . ? C13B C14B H14B 120.2 . . ? N3B C15B C14B 123.1(4) . . ? N3B C15B H15B 118.5 . . ? C14B C15B H15B 118.5 . . ? N4B C16B O2B 124.4(4) . . ? N4B C16B C13B 115.7(4) . 2_645 ? O2B C16B C13B 119.8(4) . 2_645 ? 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 O3 H3O O1B 0.87 1.81 2.669(5) 175.1 3_666 O3 H3O N4B 0.87 2.55 3.307(5) 146.8 3_666 O3 H3P O3 0.88 1.81 2.687(9) 178.9 3_666 O4 H4O O3 0.86 1.90 2.755(5) 179.1 . O4 H4P O2B 0.86 2.01 2.868(5) 175.2 . O5 H5O O2 0.88 1.99 2.863(5) 168.4 . O6 H6O O5 0.87 1.95 2.760(5) 154.1 . O6 H6P O1 0.86 2.08 2.809(5) 141.9 3_565 O7 H7O O10 0.86 2.09 2.949(5) 174.7 4_565 O8 H8O O5 0.86 1.90 2.756(5) 179.1 . O8 H8P O7 0.86 1.95 2.789(5) 165.0 . O9 H9O O8 0.86 1.93 2.785(5) 177.5 . O9 H9P O4 0.86 1.93 2.765(6) 163.7 . O10 H10E O3 0.84 2.56 3.110(6) 124.2 . O10 H10E O4 0.84 2.41 3.231(6) 165.0 . O10 H10D O1 0.84 1.90 2.736(5) 175.3 2_545 O11 H11A O10 0.88 2.28 2.96(2) 134.1 2 N4 H4N O11 0.88 1.78 2.549(15) 145.1 . N4 H4N O9 0.88 2.47 3.095(6) 128.7 2 N4B H4M O7 0.88 2.06 2.765(5) 135.8 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.926 _refine_diff_density_min -0.756 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 962654' ####################################################################### # # 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_ig80d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H17 Cu N2 O4 S2, Cl O4' _chemical_formula_sum 'C10 H17 Cl Cu N2 O8 S2' _chemical_formula_weight 456.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7094(3) _cell_length_b 9.5978(3) _cell_length_c 10.6996(3) _cell_angle_alpha 96.294(2) _cell_angle_beta 102.423(2) _cell_angle_gamma 95.889(2) _cell_volume 860.82(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3729 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 466 _exptl_absorpt_coefficient_mu 1.707 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7648 _exptl_absorpt_correction_T_max 0.9030 _exptl_absorpt_process_details 'Xprep in Shelxtl v.6.14-1 (Sheldrick, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16273 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3935 _reflns_number_gt 3115 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Crystal Impact GbR, 2006)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0363P)^2^+0.8806P] 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 3935 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0778 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 -0.12786(3) 0.03691(3) 0.85283(3) 0.01563(10) Uani 1 1 d . . . Cl1 Cl 0.29936(8) -0.47480(7) 0.73335(6) 0.02506(16) Uani 1 1 d . . . S1 S -0.10800(8) -0.27485(7) 0.76737(6) 0.02033(15) Uani 1 1 d . . . S2 S -0.25149(9) 0.08802(8) 0.52019(7) 0.02864(18) Uani 1 1 d . . . O1 O -0.0435(2) 0.23580(19) 0.86708(18) 0.0198(4) Uani 1 1 d . . . O2 O 0.0906(2) 0.00583(19) 0.87545(18) 0.0194(4) Uani 1 1 d . . . O3 O -0.1890(2) -0.17068(19) 0.84275(17) 0.0181(4) Uani 1 1 d . . . O4 O -0.2036(3) -0.0040(2) 0.62382(18) 0.0282(5) Uani 1 1 d . . . O5 O 0.3726(3) -0.3379(3) 0.7260(2) 0.0493(7) Uani 1 1 d . . . O6 O 0.3848(4) -0.5814(3) 0.6929(2) 0.0563(8) Uani 1 1 d . . . O7 O 0.2800(3) -0.4852(2) 0.86367(18) 0.0287(5) Uani 1 1 d . . . O8 O 0.1424(3) -0.4953(3) 0.6478(2) 0.0471(6) Uani 1 1 d . . . N1 N -0.3442(2) 0.0753(2) 0.8647(2) 0.0157(4) Uani 1 1 d . . . N2 N 0.1157(2) 0.2393(2) 0.8700(2) 0.0168(4) Uani 1 1 d . . . H2N H 0.164(4) 0.321(3) 0.865(3) 0.018(7) Uiso 1 1 d . . . C1 C 0.1775(3) 0.1210(3) 0.8751(2) 0.0161(5) Uani 1 1 d . . . C2 C 0.3473(3) 0.1151(3) 0.8741(2) 0.0160(5) Uani 1 1 d . . . C3 C 0.3815(3) -0.0145(3) 0.8225(2) 0.0158(5) Uani 1 1 d . . . H3 H 0.2995 -0.0914 0.7907 0.019 Uiso 1 1 calc R . . C4 C -0.4640(3) -0.0299(3) 0.8181(2) 0.0182(5) Uani 1 1 d . . . H4 H -0.4415 -0.1178 0.7809 0.022 Uiso 1 1 calc R . . C5 C -0.3768(3) 0.1998(3) 0.9161(2) 0.0168(5) Uani 1 1 d . . . H5 H -0.2920 0.2739 0.9499 0.020 Uiso 1 1 calc R . . C6 C 0.4698(3) 0.2245(3) 0.9217(3) 0.0179(5) Uani 1 1 d . . . H6 H 0.4497 0.3140 0.9573 0.022 Uiso 1 1 calc R . . C7 C -0.0760(4) 0.1976(4) 0.5145(4) 0.0408(8) Uani 1 1 d . . . H7A H -0.0235 0.2436 0.6018 0.061 Uiso 1 1 calc R . . H7B H -0.1037 0.2698 0.4586 0.061 Uiso 1 1 calc R . . H7C H -0.0042 0.1398 0.4801 0.061 Uiso 1 1 calc R . . C8 C -0.3504(4) 0.2220(4) 0.5851(3) 0.0380(8) Uani 1 1 d . . . H8A H -0.4499 0.1789 0.6013 0.057 Uiso 1 1 calc R . . H8B H -0.3732 0.2896 0.5233 0.057 Uiso 1 1 calc R . . H8C H -0.2825 0.2714 0.6663 0.057 Uiso 1 1 calc R . . C9 C -0.1142(4) -0.4265(3) 0.8492(3) 0.0282(6) Uani 1 1 d . . . H9A H -0.0440 -0.4044 0.9355 0.042 Uiso 1 1 calc R . . H9B H -0.0790 -0.5046 0.8002 0.042 Uiso 1 1 calc R . . H9C H -0.2229 -0.4541 0.8568 0.042 Uiso 1 1 calc R . . C10 C -0.2536(4) -0.3447(3) 0.6241(3) 0.0294(7) Uani 1 1 d . . . H10A H -0.3493 -0.3867 0.6472 0.044 Uiso 1 1 calc R . . H10B H -0.2119 -0.4173 0.5739 0.044 Uiso 1 1 calc R . . H10C H -0.2796 -0.2686 0.5724 0.044 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 0.01085(15) 0.01456(16) 0.02169(17) 0.00215(12) 0.00408(12) 0.00218(11) Cl1 0.0330(4) 0.0177(3) 0.0262(3) 0.0018(3) 0.0123(3) 0.0007(3) S1 0.0185(3) 0.0176(3) 0.0256(3) -0.0004(3) 0.0081(3) 0.0026(3) S2 0.0386(4) 0.0279(4) 0.0180(3) 0.0048(3) 0.0038(3) 0.0015(3) O1 0.0112(8) 0.0191(9) 0.0305(10) 0.0033(8) 0.0071(8) 0.0035(7) O2 0.0127(8) 0.0161(9) 0.0299(10) 0.0033(8) 0.0058(8) 0.0029(7) O3 0.0175(9) 0.0173(9) 0.0216(9) 0.0025(7) 0.0083(7) 0.0044(7) O4 0.0440(12) 0.0222(10) 0.0204(10) 0.0059(8) 0.0091(9) 0.0060(9) O5 0.0641(17) 0.0321(13) 0.0521(15) 0.0067(11) 0.0239(13) -0.0156(12) O6 0.091(2) 0.0541(17) 0.0372(13) 0.0095(12) 0.0242(14) 0.0486(16) O7 0.0403(12) 0.0228(10) 0.0229(10) 0.0008(8) 0.0105(9) -0.0008(9) O8 0.0372(13) 0.0625(17) 0.0353(13) 0.0030(12) -0.0004(11) 0.0007(12) N1 0.0103(9) 0.0196(11) 0.0170(10) 0.0043(9) 0.0028(8) 0.0005(8) N2 0.0110(10) 0.0164(11) 0.0235(11) 0.0031(9) 0.0055(9) 0.0000(9) C1 0.0119(11) 0.0215(13) 0.0158(12) 0.0026(10) 0.0047(10) 0.0036(10) C2 0.0133(11) 0.0210(13) 0.0150(12) 0.0046(10) 0.0046(10) 0.0036(10) C3 0.0120(11) 0.0165(12) 0.0177(12) -0.0001(10) 0.0029(10) -0.0004(9) C4 0.0154(12) 0.0177(13) 0.0216(13) 0.0006(10) 0.0051(10) 0.0035(10) C5 0.0143(12) 0.0161(12) 0.0201(13) 0.0031(10) 0.0047(10) 0.0000(10) C6 0.0157(12) 0.0168(13) 0.0218(13) 0.0022(10) 0.0050(10) 0.0036(10) C7 0.0399(19) 0.0411(19) 0.053(2) 0.0263(17) 0.0244(17) 0.0108(16) C8 0.0373(18) 0.0417(19) 0.0426(19) 0.0203(16) 0.0136(15) 0.0152(15) C9 0.0379(16) 0.0180(13) 0.0287(15) 0.0026(12) 0.0042(13) 0.0110(12) C10 0.0409(17) 0.0247(15) 0.0192(13) -0.0009(12) 0.0023(13) 0.0027(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 O2 1.9238(17) . ? Cu1 O1 1.9511(18) . ? Cu1 N1 1.984(2) . ? Cu1 O3 1.9938(18) . ? Cu1 O4 2.3736(19) . ? Cl1 O6 1.409(2) . ? Cl1 O5 1.418(2) . ? Cl1 O7 1.453(2) . ? Cl1 O8 1.454(2) . ? S1 O3 1.5362(18) . ? S1 C9 1.781(3) . ? S1 C10 1.781(3) . ? S2 O4 1.508(2) . ? S2 C8 1.779(3) . ? S2 C7 1.780(3) . ? O1 N2 1.377(3) . ? O2 C1 1.275(3) . ? N1 C5 1.343(3) . ? N1 C4 1.344(3) . ? N2 C1 1.307(3) . ? N2 H2N 0.86(3) . ? C1 C2 1.488(3) . ? C2 C6 1.385(4) . ? C2 C3 1.392(4) . ? C3 C4 1.378(3) 1_655 ? C3 H3 0.9500 . ? C4 C3 1.378(3) 1_455 ? C4 H4 0.9500 . ? C5 C6 1.393(3) 1_455 ? C5 H5 0.9500 . ? C6 C5 1.393(3) 1_655 ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 O2 Cu1 O1 84.37(7) . . ? O2 Cu1 N1 169.47(8) . . ? O1 Cu1 N1 94.61(8) . . ? O2 Cu1 O3 89.26(7) . . ? O1 Cu1 O3 173.60(7) . . ? N1 Cu1 O3 91.55(8) . . ? O2 Cu1 O4 98.91(8) . . ? O1 Cu1 O4 96.45(7) . . ? N1 Cu1 O4 91.62(8) . . ? O3 Cu1 O4 85.09(7) . . ? O6 Cl1 O5 111.86(18) . . ? O6 Cl1 O7 110.69(14) . . ? O5 Cl1 O7 110.28(13) . . ? O6 Cl1 O8 108.24(17) . . ? O5 Cl1 O8 107.77(17) . . ? O7 Cl1 O8 107.84(14) . . ? O3 S1 C9 103.46(12) . . ? O3 S1 C10 105.18(13) . . ? C9 S1 C10 98.15(14) . . ? O4 S2 C8 107.43(14) . . ? O4 S2 C7 106.39(15) . . ? C8 S2 C7 97.71(17) . . ? N2 O1 Cu1 106.32(14) . . ? C1 O2 Cu1 110.28(15) . . ? S1 O3 Cu1 119.96(10) . . ? S2 O4 Cu1 134.33(11) . . ? C5 N1 C4 118.7(2) . . ? C5 N1 Cu1 123.69(17) . . ? C4 N1 Cu1 117.64(17) . . ? C1 N2 O1 118.3(2) . . ? C1 N2 H2N 127(2) . . ? O1 N2 H2N 115(2) . . ? O2 C1 N2 120.1(2) . . ? O2 C1 C2 118.3(2) . . ? N2 C1 C2 121.6(2) . . ? C6 C2 C3 119.1(2) . . ? C6 C2 C1 125.8(2) . . ? C3 C2 C1 115.1(2) . . ? C4 C3 C2 119.1(2) 1_655 . ? C4 C3 H3 120.4 1_655 . ? C2 C3 H3 120.4 . . ? N1 C4 C3 122.3(2) . 1_455 ? N1 C4 H4 118.9 . . ? C3 C4 H4 118.9 1_455 . ? N1 C5 C6 122.5(2) . 1_455 ? N1 C5 H5 118.8 . . ? C6 C5 H5 118.8 1_455 . ? C2 C6 C5 118.4(2) . 1_655 ? C2 C6 H6 120.8 . . ? C5 C6 H6 120.8 1_655 . ? S2 C7 H7A 109.5 . . ? S2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? S2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? S2 C8 H8A 109.5 . . ? S2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? S1 C9 H9A 109.5 . . ? S1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? S1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? S1 C10 H10A 109.5 . . ? S1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? S1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? 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 N2 H2N O7 0.86(3) 2.03(3) 2.890(3) 177(3) 1_565 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.799 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 962655' ####################################################################### # # 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_ig79dx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H11 Cl Cu N2 O7 S, C2 H6 O S' _chemical_formula_sum 'C10 H17 Cl Cu N2 O8 S2' _chemical_formula_weight 456.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.9002(3) _cell_length_b 12.4076(4) _cell_length_c 12.8803(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.500(2) _cell_angle_gamma 90.00 _cell_volume 1722.87(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7408 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 1.706 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7591 _exptl_absorpt_correction_T_max 0.9226 _exptl_absorpt_process_details 'SADABS v.2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35744 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3953 _reflns_number_gt 3325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Brandenburg, 2006)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0298P)^2^+2.1788P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3953 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.58850(3) 0.07471(2) 0.44608(2) 0.01407(9) Uani 1 1 d . . . Cl1 Cl 0.84242(5) 0.11505(5) 0.27866(4) 0.01978(13) Uani 1 1 d . . . S1 S 0.81755(5) 0.02506(5) 0.60819(4) 0.01617(13) Uani 1 1 d . . . S2 S 0.81000(6) -0.26330(5) 0.48671(5) 0.02099(14) Uani 1 1 d . . . O1 O 0.49672(14) 0.03542(12) 0.30821(12) 0.0152(3) Uani 1 1 d . . . O2 O 0.59541(14) -0.07921(12) 0.46741(12) 0.0151(3) Uani 1 1 d . . . O3 O 0.70031(15) 0.09366(13) 0.57869(12) 0.0178(3) Uani 1 1 d . . . O4 O 0.70276(16) -0.31006(14) 0.41163(15) 0.0280(4) Uani 1 1 d . . . O5 O 0.79080(18) 0.05018(17) 0.35424(16) 0.0343(5) Uani 1 1 d . . . O6 O 0.85984(19) 0.04998(19) 0.19016(15) 0.0419(5) Uani 1 1 d . . . O7 O 0.96146(18) 0.15494(18) 0.32735(16) 0.0378(5) Uani 1 1 d . . . O8 O 0.76119(19) 0.20295(17) 0.24636(16) 0.0380(5) Uani 1 1 d . . . N1 N 0.56243(18) -0.12644(16) 0.37050(14) 0.0137(4) Uani 1 1 d . . . N2 N 0.41993(17) -0.26689(15) 0.07758(14) 0.0137(4) Uani 1 1 d . . . C1 C 0.5109(2) -0.06561(17) 0.29352(17) 0.0129(4) Uani 1 1 d . . . C2 C 0.4660(2) -0.11363(18) 0.18977(17) 0.0132(4) Uani 1 1 d . . . C3 C 0.4635(2) -0.22427(17) 0.17167(17) 0.0141(4) Uani 1 1 d . . . H3 H 0.4937 -0.2713 0.2279 0.017 Uiso 1 1 calc R . . C4 C 0.3765(2) -0.19959(19) -0.00158(18) 0.0174(5) Uani 1 1 d . . . H4 H 0.3463 -0.2293 -0.0685 0.021 Uiso 1 1 calc R . . C5 C 0.3741(2) -0.08923(19) 0.01098(18) 0.0196(5) Uani 1 1 d . . . H5 H 0.3418 -0.0440 -0.0461 0.024 Uiso 1 1 calc R . . C6 C 0.4196(2) -0.04528(19) 0.10783(18) 0.0169(5) Uani 1 1 d . . . H6 H 0.4190 0.0305 0.1181 0.020 Uiso 1 1 calc R . . C7 C 0.8283(2) 0.0151(2) 0.74697(18) 0.0231(5) Uani 1 1 d . . . H7A H 0.8145 0.0862 0.7763 0.035 Uiso 1 1 calc R . . H7B H 0.9110 -0.0110 0.7765 0.035 Uiso 1 1 calc R . . H7C H 0.7655 -0.0354 0.7646 0.035 Uiso 1 1 calc R . . C8 C 0.9413(2) 0.1176(2) 0.6018(2) 0.0232(5) Uani 1 1 d . . . H8A H 0.9429 0.1381 0.5285 0.035 Uiso 1 1 calc R . . H8B H 1.0202 0.0835 0.6303 0.035 Uiso 1 1 calc R . . H8C H 0.9287 0.1820 0.6429 0.035 Uiso 1 1 calc R . . C9 C 0.9268(2) -0.3659(2) 0.5030(2) 0.0278(6) Uani 1 1 d . . . H9A H 0.8899 -0.4343 0.5208 0.042 Uiso 1 1 calc R . . H9B H 0.9928 -0.3453 0.5597 0.042 Uiso 1 1 calc R . . H9C H 0.9615 -0.3743 0.4375 0.042 Uiso 1 1 calc R . . C10 C 0.7665(3) -0.2714(2) 0.6143(2) 0.0282(6) Uani 1 1 d . . . H10A H 0.6977 -0.2217 0.6191 0.042 Uiso 1 1 calc R . . H10B H 0.8374 -0.2518 0.6669 0.042 Uiso 1 1 calc R . . H10C H 0.7404 -0.3452 0.6272 0.042 Uiso 1 1 calc R . . H2N H 0.589(2) -0.190(2) 0.365(2) 0.018(7) 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 0.01855(15) 0.01038(14) 0.01229(15) 0.00036(10) -0.00097(10) -0.00058(11) Cl1 0.0181(3) 0.0244(3) 0.0168(3) 0.0011(2) 0.0023(2) 0.0026(2) S1 0.0173(3) 0.0152(3) 0.0151(3) 0.0012(2) -0.0005(2) 0.0005(2) S2 0.0196(3) 0.0154(3) 0.0265(3) 0.0006(2) -0.0015(2) -0.0007(2) O1 0.0202(8) 0.0097(7) 0.0147(8) -0.0005(6) -0.0004(6) 0.0005(6) O2 0.0206(8) 0.0124(8) 0.0109(7) -0.0023(6) -0.0018(6) -0.0002(6) O3 0.0179(8) 0.0163(8) 0.0173(8) 0.0005(6) -0.0030(6) 0.0023(7) O4 0.0248(10) 0.0162(9) 0.0384(11) -0.0048(8) -0.0109(8) 0.0019(7) O5 0.0293(11) 0.0383(11) 0.0372(11) 0.0164(9) 0.0112(9) 0.0030(9) O6 0.0362(12) 0.0623(15) 0.0258(10) -0.0191(10) 0.0000(9) 0.0137(11) O7 0.0257(10) 0.0454(13) 0.0407(12) -0.0075(10) -0.0004(9) -0.0101(9) O8 0.0397(12) 0.0391(12) 0.0371(12) 0.0152(9) 0.0121(9) 0.0194(10) N1 0.0180(10) 0.0094(9) 0.0129(9) -0.0026(7) -0.0002(7) 0.0001(8) N2 0.0159(10) 0.0105(9) 0.0149(9) -0.0001(7) 0.0036(7) 0.0000(7) C1 0.0118(10) 0.0116(10) 0.0154(11) 0.0001(8) 0.0027(8) -0.0002(8) C2 0.0140(11) 0.0129(10) 0.0131(11) -0.0008(8) 0.0032(8) -0.0007(8) C3 0.0144(11) 0.0124(10) 0.0154(11) 0.0005(8) 0.0024(8) 0.0006(8) C4 0.0208(12) 0.0174(11) 0.0131(11) -0.0010(9) -0.0010(9) -0.0012(9) C5 0.0258(13) 0.0174(12) 0.0148(11) 0.0033(9) -0.0002(9) 0.0025(10) C6 0.0197(12) 0.0132(11) 0.0175(11) 0.0003(9) 0.0019(9) 0.0017(9) C7 0.0201(12) 0.0319(14) 0.0172(12) 0.0079(10) 0.0021(9) 0.0059(10) C8 0.0191(12) 0.0255(13) 0.0244(13) 0.0056(10) 0.0014(10) -0.0030(10) C9 0.0232(13) 0.0267(14) 0.0319(15) 0.0000(11) -0.0006(11) 0.0056(11) C10 0.0243(14) 0.0271(14) 0.0343(15) 0.0004(11) 0.0075(11) -0.0008(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 O2 1.9293(15) . ? Cu1 O3 1.9602(16) . ? Cu1 O1 1.9664(15) . ? Cu1 N2 1.9888(18) 2_655 ? Cu1 O2 2.4340(16) 3_656 ? Cu1 O5 2.6693(19) . ? Cu1 Cu1 3.1435(5) 3_656 ? Cl1 O8 1.427(2) . ? Cl1 O6 1.432(2) . ? Cl1 O5 1.4402(19) . ? Cl1 O7 1.443(2) . ? S1 O3 1.5358(16) . ? S1 C7 1.778(2) . ? S1 C8 1.782(2) . ? S2 O4 1.5178(18) . ? S2 C10 1.779(3) . ? S2 C9 1.791(3) . ? O1 C1 1.281(3) . ? O2 N1 1.378(2) . ? O2 Cu1 2.4340(16) 3_656 ? N1 C1 1.305(3) . ? N1 H2N 0.85(3) . ? N2 C3 1.343(3) . ? N2 C4 1.349(3) . ? N2 Cu1 1.9888(18) 2_645 ? C1 C2 1.479(3) . ? C2 C6 1.390(3) . ? C2 C3 1.392(3) . ? C3 H3 0.9500 . ? C4 C5 1.379(3) . ? C4 H4 0.9500 . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 O2 Cu1 O3 89.34(6) . . ? O2 Cu1 O1 83.52(6) . . ? O3 Cu1 O1 169.87(6) . . ? O2 Cu1 N2 179.30(7) . 2_655 ? O3 Cu1 N2 91.36(7) . 2_655 ? O1 Cu1 N2 95.79(7) . 2_655 ? O2 Cu1 O2 88.56(6) . 3_656 ? O3 Cu1 O2 92.66(6) . 3_656 ? O1 Cu1 O2 94.33(6) . 3_656 ? N2 Cu1 O2 91.43(6) 2_655 3_656 ? O2 Cu1 O5 86.15(6) . . ? O3 Cu1 O5 87.24(7) . . ? O1 Cu1 O5 85.12(6) . . ? N2 Cu1 O5 93.86(7) 2_655 . ? O2 Cu1 O5 174.71(6) 3_656 . ? O2 Cu1 Cu1 50.72(5) . 3_656 ? O3 Cu1 Cu1 91.65(5) . 3_656 ? O1 Cu1 Cu1 89.38(5) . 3_656 ? N2 Cu1 Cu1 129.27(5) 2_655 3_656 ? O2 Cu1 Cu1 37.85(4) 3_656 3_656 ? O5 Cu1 Cu1 136.86(5) . 3_656 ? O2 Cu1 Cu1 148.50(5) . 2_655 ? O3 Cu1 Cu1 120.97(5) . 2_655 ? O1 Cu1 Cu1 65.28(4) . 2_655 ? N2 Cu1 Cu1 30.82(5) 2_655 2_655 ? O2 Cu1 Cu1 97.60(4) 3_656 2_655 ? O5 Cu1 Cu1 86.96(4) . 2_655 ? Cu1 Cu1 Cu1 128.737(13) 3_656 2_655 ? O8 Cl1 O6 110.38(13) . . ? O8 Cl1 O5 109.66(12) . . ? O6 Cl1 O5 109.50(14) . . ? O8 Cl1 O7 110.12(14) . . ? O6 Cl1 O7 108.84(13) . . ? O5 Cl1 O7 108.31(12) . . ? O3 S1 C7 102.49(11) . . ? O3 S1 C8 103.84(11) . . ? C7 S1 C8 98.83(12) . . ? O4 S2 C10 106.35(12) . . ? O4 S2 C9 105.67(12) . . ? C10 S2 C9 97.66(13) . . ? C1 O1 Cu1 108.64(14) . . ? N1 O2 Cu1 107.02(12) . . ? N1 O2 Cu1 107.59(12) . 3_656 ? Cu1 O2 Cu1 91.44(6) . 3_656 ? S1 O3 Cu1 122.45(10) . . ? Cl1 O5 Cu1 131.81(11) . . ? C1 N1 O2 117.88(18) . . ? C1 N1 H2N 125.9(18) . . ? O2 N1 H2N 115.4(18) . . ? C3 N2 C4 118.44(19) . . ? C3 N2 Cu1 121.97(15) . 2_645 ? C4 N2 Cu1 119.53(15) . 2_645 ? O1 C1 N1 120.1(2) . . ? O1 C1 C2 119.79(19) . . ? N1 C1 C2 120.08(19) . . ? C6 C2 C3 118.6(2) . . ? C6 C2 C1 118.4(2) . . ? C3 C2 C1 123.0(2) . . ? N2 C3 C2 122.3(2) . . ? N2 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? N2 C4 C5 122.4(2) . . ? N2 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C4 C5 C6 119.1(2) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C2 119.1(2) . . ? C5 C6 H6 120.5 . . ? C2 C6 H6 120.5 . . ? S1 C7 H7A 109.5 . . ? S1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? S1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? S1 C8 H8A 109.5 . . ? S1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? S2 C9 H9A 109.5 . . ? S2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? S2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? S2 C10 H10A 109.5 . . ? S2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? S2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? 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 H2N O4 0.85(3) 1.98(3) 2.752(3) 152(3) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.527 _refine_diff_density_min -0.526 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 962656' ####################################################################### # # 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_ig188dm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H13 Cu N4 O2, Cl O4' _chemical_formula_sum 'C18 H13 Cl Cu N4 O6' _chemical_formula_weight 480.31 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M '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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 16.1013(4) _cell_length_b 12.1614(2) _cell_length_c 18.9485(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3710.39(15) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 13625 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1944 _exptl_absorpt_coefficient_mu 1.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7801 _exptl_absorpt_correction_T_max 0.8552 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42119 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3633 _reflns_number_gt 2897 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond v.3.1d (Crystal Impact GbR, 2006)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0654P)^2^+5.5738P] 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 3633 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1275 _refine_ls_wR_factor_gt 0.1155 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 0.45986(3) 0.12624(3) 0.53569(2) 0.02813(15) Uani 1 1 d . . . Cl1 Cl 0.72348(6) 0.43166(9) 0.22264(5) 0.0448(3) Uani 1 1 d . . . O1 O 0.44944(14) 0.07622(19) 0.63198(13) 0.0306(5) Uani 1 1 d . . . O2 O 0.40338(14) -0.01207(18) 0.51270(12) 0.0281(5) Uani 1 1 d . . . O3 O 0.6817(2) 0.3408(3) 0.25231(18) 0.0640(9) Uani 1 1 d . . . O4 O 0.7103(2) 0.4461(3) 0.15027(16) 0.0719(10) Uani 1 1 d . . . O5 O 0.8076(2) 0.4427(3) 0.24303(19) 0.0753(11) Uani 1 1 d . . . O6 O 0.6835(3) 0.5327(3) 0.2538(2) 0.0934(14) Uani 1 1 d . . . N1 N 0.46880(17) 0.1866(2) 0.43767(16) 0.0287(6) Uani 1 1 d . . . N2 N 0.53349(17) 0.2521(2) 0.55921(16) 0.0295(6) Uani 1 1 d . . . N3 N 0.38989(18) -0.0037(2) 0.63007(17) 0.0291(6) Uani 1 1 d . . . H3A H 0.366(2) -0.007(3) 0.667(2) 0.028(10) Uiso 1 1 d . . . N4 N 0.17285(18) -0.2816(2) 0.54818(15) 0.0303(6) Uani 1 1 d . . . C1 C 0.4366(2) 0.1508(3) 0.3775(2) 0.0342(8) Uani 1 1 d . . . H1 H 0.4084 0.0823 0.3769 0.041 Uiso 1 1 calc R . . C2 C 0.4429(2) 0.2112(3) 0.3143(2) 0.0395(9) Uani 1 1 d . . . H2 H 0.4190 0.1835 0.2720 0.047 Uiso 1 1 calc R . . C3 C 0.4838(2) 0.3103(3) 0.3141(2) 0.0401(9) Uani 1 1 d . . . H3 H 0.4868 0.3525 0.2720 0.048 Uiso 1 1 calc R . . C4 C 0.5210(2) 0.3492(3) 0.3760(2) 0.0352(8) Uani 1 1 d . . . C5 C 0.5675(2) 0.4496(3) 0.3820(2) 0.0406(9) Uani 1 1 d . . . H5 H 0.5735 0.4954 0.3417 0.049 Uiso 1 1 calc R . . C6 C 0.6030(2) 0.4805(3) 0.4437(2) 0.0402(9) Uani 1 1 d . . . H6 H 0.6341 0.5467 0.4455 0.048 Uiso 1 1 calc R . . C7 C 0.5946(2) 0.4153(3) 0.5067(2) 0.0353(8) Uani 1 1 d . . . C8 C 0.6307(2) 0.4399(3) 0.5720(2) 0.0411(9) Uani 1 1 d . . . H8 H 0.6636 0.5041 0.5773 0.049 Uiso 1 1 calc R . . C9 C 0.6183(2) 0.3708(3) 0.6287(2) 0.0400(9) Uani 1 1 d . . . H9 H 0.6430 0.3866 0.6731 0.048 Uiso 1 1 calc R . . C10 C 0.5692(2) 0.2774(3) 0.6201(2) 0.0357(8) Uani 1 1 d . . . H10 H 0.5609 0.2301 0.6594 0.043 Uiso 1 1 calc R . . C11 C 0.5462(2) 0.3191(3) 0.50285(19) 0.0301(7) Uani 1 1 d . . . C12 C 0.5106(2) 0.2848(3) 0.43732(19) 0.0302(7) Uani 1 1 d . . . C13 C 0.3684(2) -0.0462(3) 0.56891(18) 0.0274(7) Uani 1 1 d . . . C14 C 0.3033(2) -0.1326(3) 0.56545(19) 0.0278(7) Uani 1 1 d . . . C15 C 0.2643(2) -0.1793(3) 0.62358(19) 0.0315(7) Uani 1 1 d . . . H15 H 0.2817 -0.1615 0.6701 0.038 Uiso 1 1 calc R . . C16 C 0.1997(2) -0.2520(3) 0.61250(19) 0.0336(8) Uani 1 1 d . . . H16 H 0.1728 -0.2828 0.6525 0.040 Uiso 1 1 calc R . . C17 C 0.2136(2) -0.2402(3) 0.49253(19) 0.0324(7) Uani 1 1 d . . . H17 H 0.1974 -0.2632 0.4466 0.039 Uiso 1 1 calc R . . C18 C 0.2780(2) -0.1657(3) 0.49869(18) 0.0298(7) Uani 1 1 d . . . H18 H 0.3047 -0.1375 0.4578 0.036 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 0.0272(2) 0.0261(2) 0.0311(3) 0.00098(16) -0.00002(17) -0.00268(16) Cl1 0.0397(5) 0.0626(6) 0.0320(5) 0.0097(4) -0.0047(4) -0.0133(5) O1 0.0286(13) 0.0298(12) 0.0333(13) 0.0021(10) -0.0021(10) -0.0052(10) O2 0.0261(12) 0.0275(11) 0.0308(12) 0.0004(9) 0.0024(10) -0.0018(9) O3 0.071(2) 0.0570(18) 0.064(2) 0.0117(16) -0.0041(17) -0.0181(17) O4 0.069(2) 0.110(3) 0.0361(17) 0.0073(18) -0.0117(16) -0.021(2) O5 0.058(2) 0.104(3) 0.064(2) 0.012(2) -0.0173(18) -0.020(2) O6 0.112(4) 0.070(2) 0.098(3) -0.009(2) 0.029(3) 0.000(2) N1 0.0241(14) 0.0286(14) 0.0333(15) -0.0004(12) 0.0011(12) 0.0006(11) N2 0.0251(14) 0.0290(14) 0.0346(15) -0.0007(12) 0.0027(12) 0.0013(12) N3 0.0264(15) 0.0315(15) 0.0296(16) 0.0021(12) 0.0015(13) -0.0015(12) N4 0.0259(15) 0.0292(14) 0.0359(16) -0.0013(12) 0.0002(12) -0.0013(11) C1 0.0318(19) 0.0335(18) 0.037(2) -0.0028(15) 0.0025(16) -0.0001(15) C2 0.040(2) 0.045(2) 0.033(2) -0.0017(16) 0.0009(16) 0.0031(17) C3 0.041(2) 0.042(2) 0.037(2) 0.0084(16) 0.0071(17) 0.0024(17) C4 0.0303(18) 0.0364(19) 0.039(2) 0.0046(15) 0.0057(16) 0.0026(15) C5 0.036(2) 0.0352(19) 0.050(2) 0.0118(17) 0.0086(18) -0.0014(16) C6 0.0314(19) 0.0313(17) 0.058(2) 0.0039(17) 0.0070(18) -0.0056(15) C7 0.0264(18) 0.0311(17) 0.048(2) -0.0027(16) 0.0040(16) -0.0004(14) C8 0.0318(19) 0.0347(18) 0.057(2) -0.0075(17) -0.0010(18) -0.0063(16) C9 0.036(2) 0.040(2) 0.044(2) -0.0061(17) -0.0069(17) -0.0045(16) C10 0.0337(19) 0.0368(19) 0.037(2) -0.0003(15) -0.0023(16) 0.0004(15) C11 0.0236(17) 0.0273(16) 0.039(2) 0.0005(15) 0.0044(14) 0.0003(13) C12 0.0235(16) 0.0295(16) 0.0376(18) -0.0008(14) 0.0037(15) 0.0051(14) C13 0.0219(16) 0.0257(15) 0.0345(18) 0.0009(13) -0.0007(14) 0.0034(13) C14 0.0208(16) 0.0262(16) 0.0364(18) 0.0013(13) 0.0003(14) 0.0035(13) C15 0.0315(18) 0.0315(17) 0.0314(18) 0.0029(14) -0.0022(15) -0.0034(15) C16 0.0321(18) 0.0336(18) 0.0351(19) 0.0048(15) 0.0032(15) -0.0020(15) C17 0.0287(18) 0.0366(17) 0.0318(18) -0.0038(15) -0.0010(15) 0.0008(15) C18 0.0266(17) 0.0325(16) 0.0303(18) -0.0001(14) 0.0028(14) 0.0011(14) _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 O1 1.930(2) . ? Cu1 O2 1.961(2) . ? Cu1 N2 1.987(3) . ? Cu1 N1 2.002(3) . ? Cu1 N4 2.425(3) 7_665 ? Cl1 O4 1.399(3) . ? Cl1 O3 1.410(3) . ? Cl1 O5 1.414(4) . ? Cl1 O6 1.507(4) . ? O1 N3 1.365(4) . ? O2 C13 1.274(4) . ? N1 C1 1.327(5) . ? N1 C12 1.370(4) . ? N2 C10 1.325(5) . ? N2 C11 1.358(5) . ? N3 C13 1.315(4) . ? N3 H3A 0.79(4) . ? N4 C17 1.340(4) . ? N4 C16 1.342(5) . ? N4 Cu1 2.425(3) 7_655 ? C1 C2 1.408(5) . ? C1 H1 0.9500 . ? C2 C3 1.373(5) . ? C2 H2 0.9500 . ? C3 C4 1.399(6) . ? C3 H3 0.9500 . ? C4 C12 1.411(5) . ? C4 C5 1.437(5) . ? C5 C6 1.355(6) . ? C5 H5 0.9500 . ? C6 C7 1.437(5) . ? C6 H6 0.9500 . ? C7 C8 1.400(6) . ? C7 C11 1.409(5) . ? C8 C9 1.378(6) . ? C8 H8 0.9500 . ? C9 C10 1.394(5) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.430(5) . ? C13 C14 1.486(5) . ? C14 C18 1.388(5) . ? C14 C15 1.389(5) . ? C15 C16 1.382(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.383(5) . ? C17 H17 0.9500 . ? C18 H18 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 O1 Cu1 O2 84.23(10) . . ? O1 Cu1 N2 94.75(11) . . ? O2 Cu1 N2 170.88(10) . . ? O1 Cu1 N1 176.76(11) . . ? O2 Cu1 N1 98.15(10) . . ? N2 Cu1 N1 83.25(12) . . ? O1 Cu1 N4 88.68(10) . 7_665 ? O2 Cu1 N4 90.56(10) . 7_665 ? N2 Cu1 N4 98.49(10) . 7_665 ? N1 Cu1 N4 89.10(10) . 7_665 ? O4 Cl1 O3 114.7(2) . . ? O4 Cl1 O5 113.6(2) . . ? O3 Cl1 O5 115.0(2) . . ? O4 Cl1 O6 102.6(3) . . ? O3 Cl1 O6 106.2(2) . . ? O5 Cl1 O6 102.9(3) . . ? N3 O1 Cu1 105.08(19) . . ? C13 O2 Cu1 107.4(2) . . ? C1 N1 C12 118.3(3) . . ? C1 N1 Cu1 130.5(2) . . ? C12 N1 Cu1 111.1(2) . . ? C10 N2 C11 118.7(3) . . ? C10 N2 Cu1 129.2(3) . . ? C11 N2 Cu1 112.0(2) . . ? C13 N3 O1 119.2(3) . . ? C13 N3 H3A 129(3) . . ? O1 N3 H3A 111(3) . . ? C17 N4 C16 117.2(3) . . ? C17 N4 Cu1 121.9(2) . 7_655 ? C16 N4 Cu1 119.7(2) . 7_655 ? N1 C1 C2 122.1(3) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 119.6(4) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C12 116.8(3) . . ? C3 C4 C5 125.2(4) . . ? C12 C4 C5 117.9(4) . . ? C6 C5 C4 121.6(4) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C7 121.6(3) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C8 C7 C11 116.9(3) . . ? C8 C7 C6 125.3(3) . . ? C11 C7 C6 117.8(3) . . ? C9 C8 C7 120.0(3) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 119.2(4) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? N2 C10 C9 122.5(4) . . ? N2 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? N2 C11 C7 122.8(3) . . ? N2 C11 C12 116.6(3) . . ? C7 C11 C12 120.6(3) . . ? N1 C12 C4 123.1(3) . . ? N1 C12 C11 116.5(3) . . ? C4 C12 C11 120.4(3) . . ? O2 C13 N3 119.5(3) . . ? O2 C13 C14 120.4(3) . . ? N3 C13 C14 120.2(3) . . ? C18 C14 C15 118.2(3) . . ? C18 C14 C13 116.9(3) . . ? C15 C14 C13 125.0(3) . . ? C16 C15 C14 118.8(3) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? N4 C16 C15 123.5(3) . . ? N4 C16 H16 118.3 . . ? C15 C16 H16 118.3 . . ? N4 C17 C18 123.2(3) . . ? N4 C17 H17 118.4 . . ? C18 C17 H17 118.4 . . ? C17 C18 C14 119.1(3) . . ? C17 C18 H18 120.4 . . ? C14 C18 H18 120.4 . . ? 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 N3 H3A O5 0.79(4) 2.11(4) 2.844(5) 155(4) 3_456 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.068 _refine_diff_density_min -0.837 _refine_diff_density_rms 0.133 _database_code_depnum_ccdc_archive 'CCDC 962657' ####################################################################### # # 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_97dx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 Cl2 Cu N4 O12' _chemical_formula_sum 'C12 H12 Cl2 Cu N4 O12' _chemical_formula_weight 538.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_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 14.1287(7) _cell_length_b 8.6553(3) _cell_length_c 15.7370(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.535(2) _cell_angle_gamma 90.00 _cell_volume 1802.17(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6668 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour green _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 1.985 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 1.587 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7097 _exptl_absorpt_correction_T_max 0.8324 _exptl_absorpt_process_details 'SADABS v.2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_method '\f scans and \w scans with \k offset' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10729 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.51 _reflns_number_total 2057 _reflns_number_gt 1746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0530P)^2^+2.0829P] 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 2057 _refine_ls_number_parameters 178 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0912 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.2500 0.7500 0.5000 0.01757(14) Uani 1 2 d S . . Cl1 Cl -0.03389(4) 0.76488(5) 0.40513(4) 0.02137(16) Uani 1 1 d D . . O1 O 0.27029(11) 0.88460(16) 0.60226(9) 0.0197(3) Uani 1 1 d . . . O2 O 0.29805(11) 0.92226(15) 0.44917(9) 0.0190(3) Uani 1 1 d . . . O3 O 0.05127(13) 0.8602(2) 0.41080(13) 0.0376(4) Uani 1 1 d . A . O4 O -0.0112(15) 0.6128(14) 0.3842(13) 0.038(3) Uani 0.48(4) 1 d PD A 1 O5 O -0.1253(9) 0.819(2) 0.3407(12) 0.043(3) Uani 0.48(4) 1 d PD A 1 O6 O -0.0343(14) 0.7627(19) 0.4973(6) 0.037(3) Uani 0.48(4) 1 d PD A 1 O4B O -0.0174(14) 0.6030(11) 0.4091(13) 0.039(3) Uani 0.52(4) 1 d PD A 2 O5B O -0.1136(11) 0.799(2) 0.3198(8) 0.041(2) Uani 0.52(4) 1 d PD A 2 O6B O -0.0794(17) 0.8070(14) 0.4730(12) 0.047(4) Uani 0.52(4) 1 d PD A 2 N1 N 0.32457(13) 1.03670(19) 0.51363(11) 0.0167(3) Uani 1 1 d . . . H1N H 0.360(2) 1.110(3) 0.5040(17) 0.027(6) Uiso 1 1 d . . . N2 N 0.36369(13) 1.1779(2) 0.81671(11) 0.0178(3) Uani 1 1 d . . . H2N H 0.3600(19) 1.147(3) 0.8662(18) 0.029(7) Uiso 1 1 d . . . C1 C 0.30986(14) 1.0108(2) 0.59012(13) 0.0162(4) Uani 1 1 d . . . C2 C 0.33853(14) 1.1282(2) 0.66305(13) 0.0160(4) Uani 1 1 d . . . C3 C 0.35754(16) 1.2836(2) 0.65181(14) 0.0185(4) Uani 1 1 d . . . H3 H 0.3556 1.3205 0.5944 0.022 Uiso 1 1 calc R . . C4 C 0.37929(15) 1.3842(2) 0.72515(15) 0.0203(4) Uani 1 1 d . . . H4 H 0.3922 1.4903 0.7182 0.024 Uiso 1 1 calc R . . C5 C 0.38190(15) 1.3281(2) 0.80821(14) 0.0196(4) Uani 1 1 d . . . H5 H 0.3965 1.3955 0.8589 0.024 Uiso 1 1 calc R . . C6 C 0.34182(14) 1.0780(2) 0.74764(13) 0.0178(4) Uani 1 1 d . . . H6 H 0.3286 0.9728 0.7566 0.021 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 0.0231(2) 0.0171(2) 0.0166(2) -0.00280(12) 0.01207(16) -0.00409(12) Cl1 0.0266(3) 0.0175(3) 0.0242(3) 0.00224(17) 0.0143(2) -0.00120(17) O1 0.0255(7) 0.0182(7) 0.0192(7) -0.0028(5) 0.0128(6) -0.0051(6) O2 0.0247(7) 0.0182(7) 0.0172(7) -0.0046(5) 0.0110(6) -0.0050(6) O3 0.0312(9) 0.0339(9) 0.0533(11) -0.0009(8) 0.0218(8) -0.0089(7) O4 0.030(4) 0.024(3) 0.046(7) -0.010(3) -0.003(4) 0.004(3) O5 0.016(2) 0.039(5) 0.072(6) 0.024(5) 0.013(4) 0.014(2) O6 0.045(6) 0.050(5) 0.022(3) -0.007(2) 0.019(3) -0.024(4) O4B 0.031(3) 0.019(2) 0.058(7) 0.011(3) 0.002(5) 0.0050(17) O5B 0.036(4) 0.032(4) 0.055(4) 0.014(3) 0.013(3) 0.007(3) O6B 0.066(8) 0.047(4) 0.045(5) -0.016(3) 0.042(6) -0.020(4) N1 0.0184(8) 0.0168(8) 0.0176(8) -0.0024(6) 0.0098(7) -0.0024(6) N2 0.0211(9) 0.0193(8) 0.0154(8) -0.0001(7) 0.0094(7) -0.0011(7) C1 0.0157(9) 0.0164(9) 0.0176(9) 0.0008(7) 0.0073(7) 0.0021(7) C2 0.0152(9) 0.0179(9) 0.0163(10) -0.0002(7) 0.0072(7) 0.0016(7) C3 0.0188(10) 0.0202(9) 0.0193(10) 0.0016(8) 0.0102(8) 0.0010(8) C4 0.0211(10) 0.0171(9) 0.0261(10) -0.0007(8) 0.0126(8) -0.0006(8) C5 0.0196(10) 0.0185(10) 0.0222(10) -0.0037(8) 0.0093(8) -0.0009(8) C6 0.0182(10) 0.0167(9) 0.0208(10) -0.0008(7) 0.0098(8) -0.0010(7) _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 O1 1.9250(13) . ? Cu1 O1 1.9250(13) 7_566 n Cu1 O2 1.9248(14) . ? Cu1 O2 1.9248(14) 7_566 n Cu1 O3 2.8282(18) . ? Cl1 O5 1.412(10) . ? Cl1 O4B 1.418(9) . ? Cl1 O4 1.420(10) . ? Cl1 O3 1.4356(16) . ? Cl1 O5B 1.449(10) . ? Cl1 O6 1.453(5) . ? Cl1 O6B 1.473(6) . ? O1 C1 1.272(2) . ? O2 N1 1.373(2) . ? N1 C1 1.311(3) . ? N1 H1N 0.86(3) . n N2 C6 1.337(3) . ? N2 C5 1.341(3) . ? N2 H2N 0.84(3) . n C1 C2 1.479(3) . ? C2 C6 1.385(3) . ? C2 C3 1.395(3) . ? C3 C4 1.391(3) . ? C3 H3 0.9500 . n C4 C5 1.383(3) . ? C4 H4 0.9500 . n C5 H5 0.9500 . n C6 H6 0.9500 . n 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 O2 Cu1 O2 180.00(5) . 7_566 ? O2 Cu1 O1 84.71(6) . . ? O2 Cu1 O1 95.29(6) 7_566 . ? O2 Cu1 O1 95.29(6) . 7_566 n O2 Cu1 O1 84.71(6) 7_566 7_566 n O1 Cu1 O1 180.0 . 7_566 ? O2 Cu1 O3 88.05(5) . . ? O2 Cu1 O3 91.95(5) 7_566 . ? O1 Cu1 O3 92.39(6) . . ? O1 Cu1 O3 87.61(6) 7_566 . ? O5 Cl1 O4 111.2(11) . . ? O5 Cl1 O3 113.0(8) . . ? O4 Cl1 O3 107.1(9) . . ? O4B Cl1 O5B 107.8(10) . . n O5 Cl1 O6 113.5(5) . . ? O4 Cl1 O6 107.5(5) . . ? O3 Cl1 O6 104.0(3) . . ? O4B Cl1 O6B 108.6(5) . . n O5B Cl1 O6B 103.1(6) . . n C1 O1 Cu1 109.79(12) . . n N1 O2 Cu1 107.25(10) . . n Cl1 O3 Cu1 120.10(10) . . n C1 N1 O2 117.72(16) . . ? C1 N1 H1N 125.5(17) . . n O2 N1 H1N 115.6(17) . . n C6 N2 C5 122.90(18) . . ? C6 N2 H2N 118.2(18) . . n C5 N2 H2N 118.6(18) . . n O1 C1 N1 120.31(17) . . ? O1 C1 C2 119.25(17) . . ? N1 C1 C2 120.43(17) . . ? C6 C2 C3 118.76(18) . . ? C6 C2 C1 115.97(17) . . ? C3 C2 C1 125.21(18) . . ? C4 C3 C2 119.64(19) . . ? C4 C3 H3 120.2 . . n C2 C3 H3 120.2 . . n C5 C4 C3 119.30(19) . . ? C5 C4 H4 120.3 . . n C3 C4 H4 120.3 . . n N2 C5 C4 119.48(18) . . ? N2 C5 H5 120.3 . . n C4 C5 H5 120.3 . . n N2 C6 C2 119.91(18) . . ? N2 C6 H6 120.0 . . n C2 C6 H6 120.0 . . n loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cu1 O1 C1 -4.25(13) . . . . n O2 Cu1 O1 C1 175.75(13) 7_566 . . . n O3 Cu1 O1 C1 -92.07(13) . . . . n O1 Cu1 O2 N1 3.42(11) . . . . n O1 Cu1 O2 N1 -176.58(11) 7_566 . . . n O3 Cu1 O2 N1 95.99(11) . . . . n O5 Cl1 O3 Cu1 -165.3(10) . . . . n O4B Cl1 O3 Cu1 -26.0(9) . . . . n O4 Cl1 O3 Cu1 -42.4(8) . . . . n O5B Cl1 O3 Cu1 -147.0(7) . . . . n O6 Cl1 O3 Cu1 71.2(10) . . . . n O6B Cl1 O3 Cu1 100.2(11) . . . . n O2 Cu1 O3 Cl1 168.24(12) . . . . n O2 Cu1 O3 Cl1 -11.76(12) 7_566 . . . n O1 Cu1 O3 Cl1 -107.14(11) . . . . n O1 Cu1 O3 Cl1 72.86(11) 7_566 . . . n Cu1 O2 N1 C1 -2.21(19) . . . . n Cu1 O1 C1 N1 4.3(2) . . . . n Cu1 O1 C1 C2 -176.03(13) . . . . n O2 N1 C1 O1 -1.5(3) . . . . n O2 N1 C1 C2 178.89(16) . . . . n O1 C1 C2 C6 14.5(3) . . . . n N1 C1 C2 C6 -165.83(17) . . . . n O1 C1 C2 C3 -162.50(19) . . . . n N1 C1 C2 C3 17.1(3) . . . . n C6 C2 C3 C4 0.0(3) . . . . n C1 C2 C3 C4 176.98(19) . . . . n C2 C3 C4 C5 0.1(3) . . . . n C6 N2 C5 C4 -0.7(3) . . . . n C3 C4 C5 N2 0.2(3) . . . . n C5 N2 C6 C2 0.8(3) . . . . n C3 C2 C6 N2 -0.5(3) . . . . n C1 C2 C6 N2 -177.73(17) . . . . n 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 H1N O6 0.86(3) 2.02(3) 2.868(6) 169(3) 3 N1 H1N O6B 0.86(3) 2.04(3) 2.886(7) 170(3) 3 N2 H2N O2 0.84(3) 1.90(3) 2.704(2) 158(2) 6_576 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.461 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.078 _database_code_depnum_ccdc_archive 'CCDC 962658'