Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Peter Hubberstey' 'Alexander J. Blake' 'Emma L. Cade' 'David J. Parker' 'Unchulee Suksangpanya' 'Claire Wilson' _publ_contact_author_name 'Dr Peter Hubberstey' _publ_contact_author_address ; School of Chemistry Nottingham University Nottingham NG7 2RD UNITED KINGDOM ; _publ_contact_author_email PETER.HUBBERSTEY@NOTTINGHAM.AC.UK _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Hydrogen-bonded supramolecular architectures in N-(methylpyridin-2-yl)-amidino-O-alkylurea)copper(II) halides ; data_CUPYBR _database_code_depnum_ccdc_archive 'CCDC 236514' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H17 Br2 Cu N5 O2' _chemical_formula_weight 462.65 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 8.6911(5) _cell_length_b 13.1827(7) _cell_length_c 13.2750(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.128(1) _cell_angle_gamma 90.00 _cell_volume 1518.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6372 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 28.4 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.023 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 6.708 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.189 _exptl_absorpt_correction_T_max 0.462 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 10718 _diffrn_reflns_av_R_equivalents 0.051 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 28.53 _reflns_number_total 3698 _reflns_number_gt 3019 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2000)' _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^)+(0.0474P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'difference Fourier' _atom_sites_solution_hydrogens 'C-H placed geometrically, N-H and O-H located by deltaF' _refine_ls_hydrogen_treatment 'C-H riding on parent atom, N-H and O-H refined with restraints' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3533 _refine_ls_number_parameters 198 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0251 _refine_ls_wR_factor_ref 0.0669 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _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 Cu Cu 0.64824(3) 0.04190(2) 0.62081(2) 0.01968(8) Uani 1 1 d . . . C100 C 0.3221(2) 0.05468(17) 0.65375(19) 0.0225(5) Uani 1 1 d . . . H10A H 0.2943 0.0555 0.7251 0.027 Uiso 1 1 calc R . . H10B H 0.2295 0.0351 0.6115 0.027 Uiso 1 1 calc R . . N101 N 0.4456(2) -0.01954(14) 0.64082(15) 0.0189(4) Uani 1 1 d . . . C102 C 0.4129(2) -0.11356(17) 0.65945(18) 0.0189(5) Uani 1 1 d . . . N103 N 0.5223(2) -0.18989(15) 0.65172(15) 0.0201(4) Uani 1 1 d D . . H103 H 0.493(3) -0.2534(9) 0.6580(19) 0.024 Uiso 1 1 d D . . C104 C 0.6753(2) -0.17822(17) 0.63757(17) 0.0193(5) Uani 1 1 d . . . N105 N 0.7399(2) -0.09293(14) 0.62339(17) 0.0226(4) Uani 1 1 d D . . H105 H 0.8371(13) -0.097(2) 0.614(2) 0.027 Uiso 1 1 d D . . N121 N 0.2769(2) -0.14749(16) 0.68804(17) 0.0231(4) Uani 1 1 d D . . H12A H 0.194(2) -0.1088(17) 0.691(2) 0.028 Uiso 1 1 d D . . H12B H 0.261(3) -0.2120(9) 0.695(2) 0.028 Uiso 1 1 d D . . O141 O 0.74301(17) -0.26931(12) 0.64130(13) 0.0228(4) Uani 1 1 d . . . C142 C 0.9090(3) -0.27218(19) 0.6367(2) 0.0294(6) Uani 1 1 d . . . H14A H 0.9383 -0.2431 0.5726 0.044 Uiso 1 1 calc R . . H14B H 0.9446 -0.3426 0.6417 0.044 Uiso 1 1 calc R . . H14C H 0.9565 -0.2327 0.6927 0.044 Uiso 1 1 calc R . . N201 N 0.5237(2) 0.16875(14) 0.60365(15) 0.0199(4) Uani 1 1 d . . . C211 C 0.3746(2) 0.15808(17) 0.62390(17) 0.0193(5) Uani 1 1 d . . . C212 C 0.2739(3) 0.24024(18) 0.62019(19) 0.0230(5) Uani 1 1 d . . . H212 H 0.1687 0.2310 0.6339 0.028 Uiso 1 1 calc R . . C213 C 0.3276(3) 0.33469(18) 0.59657(19) 0.0259(5) Uani 1 1 d . . . H213 H 0.2606 0.3917 0.5949 0.031 Uiso 1 1 calc R . . C214 C 0.4819(3) 0.34572(18) 0.5750(2) 0.0263(5) Uani 1 1 d . . . H214 H 0.5218 0.4102 0.5580 0.032 Uiso 1 1 calc R . . C215 C 0.5753(3) 0.26143(18) 0.57890(18) 0.0233(5) Uani 1 1 d . . . H215 H 0.6802 0.2688 0.5635 0.028 Uiso 1 1 calc R . . Br1 Br 0.89089(3) 0.113318(18) 0.57192(2) 0.02718(8) Uani 1 1 d . . . Br2 Br 0.70381(3) 0.097959(17) 0.836861(19) 0.02404(8) Uani 1 1 d . . . O1S O 1.0210(2) -0.04952(16) 0.78007(16) 0.0368(5) Uani 1 1 d D . . H1S H 0.955(3) -0.006(2) 0.777(3) 0.055 Uiso 1 1 d D . . C1S C 1.0715(3) -0.0649(2) 0.8814(2) 0.0370(6) Uani 1 1 d . . . H1SA H 1.1680 -0.0279 0.8958 0.055 Uiso 1 1 calc R . . H1SB H 1.0887 -0.1375 0.8935 0.055 Uiso 1 1 calc R . . H1SC H 0.9931 -0.0401 0.9256 0.055 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 Cu 0.01517(13) 0.01338(15) 0.03062(17) 0.00050(11) 0.00239(11) -0.00049(10) C100 0.0170(10) 0.0173(11) 0.0332(14) 0.0000(10) 0.0025(9) 0.0012(9) N101 0.0157(8) 0.0141(9) 0.0269(11) -0.0010(8) 0.0005(7) 0.0019(7) C102 0.0178(10) 0.0185(11) 0.0201(12) -0.0021(9) -0.0015(8) 0.0012(8) N103 0.0199(9) 0.0127(9) 0.0277(11) 0.0008(8) 0.0005(8) -0.0009(7) C104 0.0197(10) 0.0195(11) 0.0185(11) -0.0018(9) -0.0001(8) 0.0028(9) N105 0.0160(9) 0.0154(9) 0.0365(12) 0.0002(8) 0.0033(8) 0.0001(7) N121 0.0178(9) 0.0138(10) 0.0380(12) 0.0033(9) 0.0045(8) 0.0002(8) O141 0.0201(8) 0.0149(8) 0.0336(10) 0.0005(7) 0.0045(7) 0.0017(6) C142 0.0188(11) 0.0231(13) 0.0466(17) 0.0001(12) 0.0042(11) 0.0046(9) N201 0.0199(9) 0.0163(9) 0.0233(10) 0.0001(8) -0.0007(7) -0.0005(7) C211 0.0190(10) 0.0172(11) 0.0216(12) -0.0034(9) -0.0006(9) -0.0009(9) C212 0.0207(11) 0.0204(12) 0.0278(13) -0.0014(10) -0.0008(9) 0.0013(9) C213 0.0287(12) 0.0160(11) 0.0327(14) -0.0023(10) -0.0019(10) 0.0038(9) C214 0.0296(12) 0.0140(11) 0.0349(14) 0.0013(10) -0.0008(10) -0.0024(9) C215 0.0226(11) 0.0189(12) 0.0283(13) 0.0013(10) -0.0002(9) -0.0037(9) Br1 0.01832(12) 0.02181(13) 0.04201(17) 0.00316(10) 0.00697(10) -0.00234(9) Br2 0.02645(13) 0.01529(12) 0.03052(15) 0.00013(9) 0.00287(10) 0.00287(9) O1S 0.0290(10) 0.0400(12) 0.0413(12) -0.0030(9) -0.0002(8) 0.0142(8) C1S 0.0336(14) 0.0363(16) 0.0413(17) 0.0028(13) 0.0050(12) 0.0061(12) _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 Cu N105 1.9473(19) . y Cu N101 1.9694(18) . y Cu N201 1.9983(19) . y Cu Br1 2.4299(4) . y C100 N101 1.469(3) . ? C100 C211 1.497(3) . ? C100 H10A 0.9900 . ? C100 H10B 0.9900 . ? N101 C102 1.299(3) . ? C102 N121 1.338(3) . ? C102 N103 1.392(3) . ? N103 C104 1.362(3) . ? N103 H103 0.880(10) . ? C104 N105 1.275(3) . ? C104 O141 1.337(3) . ? N105 H105 0.863(10) . ? N121 H12A 0.882(10) . ? N121 H12B 0.867(10) . ? O141 C142 1.448(3) . ? C142 H14A 0.9800 . ? C142 H14B 0.9800 . ? C142 H14C 0.9800 . ? N201 C211 1.345(3) . ? N201 C215 1.348(3) . ? C211 C212 1.391(3) . ? C212 C213 1.372(3) . ? C212 H212 0.9500 . ? C213 C214 1.394(3) . ? C213 H213 0.9500 . ? C214 C215 1.375(3) . ? C214 H214 0.9500 . ? C215 H215 0.9500 . ? O1S C1S 1.407(4) . ? O1S H1S 0.811(10) . ? C1S H1SA 0.9800 . ? C1S H1SB 0.9800 . ? C1S H1SC 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 N105 Cu N101 89.43(8) . . y N105 Cu N201 169.85(8) . . y N101 Cu N201 82.92(8) . . y N105 Cu Br1 89.90(6) . . y N101 Cu Br1 172.23(6) . . y N201 Cu Br1 96.78(5) . . y N101 C100 C211 109.90(18) . . ? N101 C100 H10A 109.7 . . ? C211 C100 H10A 109.7 . . ? N101 C100 H10B 109.7 . . ? C211 C100 H10B 109.7 . . ? H10A C100 H10B 108.2 . . ? C102 N101 C100 116.37(18) . . ? C102 N101 Cu 128.70(15) . . ? C100 N101 Cu 113.96(14) . . ? N101 C102 N121 125.4(2) . . ? N101 C102 N103 121.2(2) . . ? N121 C102 N103 113.4(2) . . ? C104 N103 C102 127.21(19) . . ? C104 N103 H103 114.2(17) . . ? C102 N103 H103 118.5(17) . . ? N105 C104 O141 126.9(2) . . ? N105 C104 N103 124.1(2) . . ? O141 C104 N103 108.94(19) . . ? C104 N105 Cu 128.65(16) . . ? C104 N105 H105 113.7(18) . . ? Cu N105 H105 117.6(18) . . ? C102 N121 H12A 123.4(18) . . ? C102 N121 H12B 120.5(18) . . ? H12A N121 H12B 115(2) . . ? C104 O141 C142 117.36(18) . . ? O141 C142 H14A 109.5 . . ? O141 C142 H14B 109.5 . . ? H14A C142 H14B 109.5 . . ? O141 C142 H14C 109.5 . . ? H14A C142 H14C 109.5 . . ? H14B C142 H14C 109.5 . . ? C211 N201 C215 118.7(2) . . ? C211 N201 Cu 114.30(15) . . ? C215 N201 Cu 126.91(16) . . ? N201 C211 C212 121.5(2) . . ? N201 C211 C100 117.29(19) . . ? C212 C211 C100 121.2(2) . . ? C213 C212 C211 119.6(2) . . ? C213 C212 H212 120.2 . . ? C211 C212 H212 120.2 . . ? C212 C213 C214 119.0(2) . . ? C212 C213 H213 120.5 . . ? C214 C213 H213 120.5 . . ? C215 C214 C213 118.7(2) . . ? C215 C214 H214 120.6 . . ? C213 C214 H214 120.6 . . ? N201 C215 C214 122.5(2) . . ? N201 C215 H215 118.7 . . ? C214 C215 H215 118.7 . . ? C1S O1S H1S 110(2) . . ? O1S C1S H1SA 109.5 . . ? O1S C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? O1S C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.971 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.112 data_cucytn _database_code_depnum_ccdc_archive 'CCDC 236515' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point unknown _chemical_formula_moiety '(C10H15N5O) Cu(II) Cl2' _chemical_formula_sum 'C10 H15 Cl2 Cu N5 O' _chemical_formula_weight 355.71 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 12.0090(6) _cell_length_b 8.5819(4) _cell_length_c 13.9542(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.305(2) _cell_angle_gamma 90.00 _cell_volume 1399.52(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 14135 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 1.941 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 0.995 _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 graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'phi and omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean '9.091 pixels/mm' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time 120 _diffrn_standards_decay_% none _diffrn_reflns_number 10261 _diffrn_reflns_av_R_equivalents 0.0764 _diffrn_reflns_av_sigmaI/netI 0.0930 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3192 _reflns_number_gt 2055 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1999); DENZO (Otwinowski and Minor, 1997)' _computing_cell_refinement 'COLLECT; DENZO' _computing_data_reduction 'COLLECT; DENZO; SORTAV' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce and Prout, 1993)' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2001)' _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^)+(0.0459P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3192 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0985 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1094 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _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 0.13803(4) 0.25806(5) 0.68709(3) 0.01894(16) Uani 1 1 d . . . Cl1 Cl 0.16356(8) 0.00075(10) 0.73170(7) 0.0228(2) Uani 1 1 d . . . Cl2 Cl 0.23331(8) 0.26354(10) 0.52846(7) 0.0225(2) Uani 1 1 d . . . N2 N 0.1061(2) 0.4828(3) 0.6836(2) 0.0177(7) Uani 1 1 d . . . C1 C 0.2010(3) 0.5815(4) 0.7327(3) 0.0210(9) Uani 1 1 d . . . H1A H 0.1768 0.6470 0.7808 0.025 Uiso 1 1 calc R . . H1B H 0.2240 0.6486 0.6847 0.025 Uiso 1 1 calc R . . C3 C 0.0166(3) 0.5544(4) 0.6328(3) 0.0179(8) Uani 1 1 d . . . N31 N 0.0041(3) 0.7092(3) 0.6248(2) 0.0224(8) Uani 1 1 d . . . H31A H 0.0581 0.7696 0.6547 0.027 Uiso 1 1 calc R . . H31B H -0.0580 0.7483 0.5896 0.027 Uiso 1 1 calc R . . N4 N -0.0775(2) 0.4743(3) 0.5798(2) 0.0192(7) Uani 1 1 d . . . H4 H -0.1316 0.5301 0.5452 0.023 Uiso 1 1 calc R . . C5 C -0.0946(3) 0.3168(4) 0.5760(3) 0.0189(8) Uani 1 1 d . . . O51 O -0.1999(2) 0.2877(3) 0.52255(19) 0.0218(6) Uani 1 1 d . . . C52 C -0.2326(3) 0.1266(4) 0.5005(3) 0.0231(9) Uani 1 1 d . . . H52A H -0.2329 0.0700 0.5607 0.028 Uiso 1 1 calc R . . H52B H -0.1794 0.0762 0.4677 0.028 Uiso 1 1 calc R . . C53 C -0.3511(3) 0.1295(4) 0.4342(3) 0.0266(10) Uani 1 1 d . . . H53A H -0.4037 0.1739 0.4691 0.040 Uiso 1 1 calc R . . H53B H -0.3745 0.0252 0.4144 0.040 Uiso 1 1 calc R . . H53C H -0.3505 0.1914 0.3770 0.040 Uiso 1 1 calc R . . N6 N -0.0202(3) 0.2185(3) 0.6183(2) 0.0208(7) Uani 1 1 d . . . H6 H -0.0422 0.1229 0.6162 0.025 Uiso 1 1 calc R . . N11 N 0.2879(3) 0.3292(4) 0.7711(2) 0.0196(7) Uani 1 1 d . . . C12 C 0.2993(3) 0.4839(4) 0.7825(3) 0.0195(8) Uani 1 1 d . . . C13 C 0.3992(3) 0.5505(4) 0.8376(3) 0.0229(9) Uani 1 1 d . . . H13 H 0.4048 0.6580 0.8462 0.027 Uiso 1 1 calc R . . C14 C 0.4901(3) 0.4555(5) 0.8792(3) 0.0268(9) Uani 1 1 d . . . H14 H 0.5581 0.4978 0.9155 0.032 Uiso 1 1 calc R . . C15 C 0.4781(3) 0.2970(5) 0.8661(3) 0.0257(9) Uani 1 1 d . . . H15 H 0.5386 0.2309 0.8931 0.031 Uiso 1 1 calc R . . C16 C 0.3770(3) 0.2367(4) 0.8131(3) 0.0223(9) Uani 1 1 d . . . H16 H 0.3693 0.1293 0.8059 0.027 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 0.0122(3) 0.0188(3) 0.0221(3) -0.00044(19) -0.00387(19) -0.00008(18) Cl1 0.0181(5) 0.0196(5) 0.0267(5) -0.0006(4) -0.0032(4) 0.0002(4) Cl2 0.0136(5) 0.0251(5) 0.0249(5) -0.0001(4) -0.0038(4) 0.0016(4) N2 0.0120(16) 0.0151(16) 0.0239(18) -0.0011(13) 0.0000(14) 0.0006(12) C1 0.015(2) 0.025(2) 0.019(2) -0.0004(15) -0.0030(17) 0.0009(16) C3 0.012(2) 0.024(2) 0.017(2) -0.0006(16) 0.0015(16) -0.0012(15) N31 0.0107(17) 0.0235(19) 0.028(2) 0.0008(14) -0.0055(14) 0.0000(13) N4 0.0130(16) 0.0174(16) 0.0225(18) -0.0010(13) -0.0056(14) 0.0009(13) C5 0.016(2) 0.023(2) 0.016(2) -0.0011(16) 0.0009(17) -0.0007(16) O51 0.0120(14) 0.0245(15) 0.0243(15) -0.0007(11) -0.0052(12) -0.0033(11) C52 0.016(2) 0.022(2) 0.028(2) -0.0018(17) -0.0015(18) 0.0009(15) C53 0.018(2) 0.022(2) 0.035(3) -0.0004(18) -0.0040(19) -0.0019(16) N6 0.0138(17) 0.0165(16) 0.0270(19) 0.0037(13) -0.0060(14) -0.0043(13) N11 0.0144(17) 0.0232(17) 0.0182(18) 0.0010(13) -0.0025(14) -0.0009(13) C12 0.016(2) 0.028(2) 0.014(2) 0.0013(16) 0.0007(16) 0.0022(16) C13 0.017(2) 0.023(2) 0.026(2) -0.0041(16) 0.0006(17) -0.0036(16) C14 0.012(2) 0.035(2) 0.029(2) -0.0009(18) -0.0049(18) -0.0008(17) C15 0.014(2) 0.035(2) 0.025(2) 0.0022(18) -0.0033(18) 0.0004(17) C16 0.015(2) 0.024(2) 0.025(2) 0.0003(17) 0.0002(17) -0.0003(16) _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 N6 1.951(3) . ? Cu1 N2 1.965(3) . ? Cu1 N11 2.004(3) . ? Cu1 Cl1 2.2956(10) . ? Cu1 Cl2 2.7161(11) . ? N2 C3 1.298(4) . ? N2 C1 1.458(4) . ? C1 C12 1.484(5) . ? C3 N31 1.339(5) . ? C3 N4 1.383(4) . ? N4 C5 1.366(5) . ? C5 N6 1.271(5) . ? C5 O51 1.336(4) . ? O51 C52 1.450(4) . ? C52 C53 1.508(5) . ? N11 C12 1.340(5) . ? N11 C16 1.352(5) . ? C12 C13 1.390(5) . ? C13 C14 1.379(5) . ? C14 C15 1.376(6) . ? C15 C16 1.370(5) . ? 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 N6 Cu1 N2 89.80(12) . . ? N6 Cu1 N11 169.34(13) . . ? N2 Cu1 N11 81.91(12) . . ? N6 Cu1 Cl1 91.15(9) . . ? N2 Cu1 Cl1 164.60(9) . . ? N11 Cu1 Cl1 95.08(9) . . ? N6 Cu1 Cl2 98.44(10) . . ? N2 Cu1 Cl2 94.54(9) . . ? N11 Cu1 Cl2 88.93(9) . . ? Cl1 Cu1 Cl2 100.52(3) . . ? C3 N2 C1 116.2(3) . . ? C3 N2 Cu1 127.6(2) . . ? C1 N2 Cu1 115.6(2) . . ? N2 C1 C12 110.1(3) . . ? N2 C3 N31 125.3(3) . . ? N2 C3 N4 121.9(3) . . ? N31 C3 N4 112.7(3) . . ? C5 N4 C3 127.5(3) . . ? N6 C5 O51 127.5(3) . . ? N6 C5 N4 123.8(3) . . ? O51 C5 N4 108.7(3) . . ? C5 O51 C52 118.2(3) . . ? O51 C52 C53 106.6(3) . . ? C5 N6 Cu1 127.8(3) . . ? C12 N11 C16 118.8(3) . . ? C12 N11 Cu1 115.1(2) . . ? C16 N11 Cu1 126.1(3) . . ? N11 C12 C13 121.7(3) . . ? N11 C12 C1 117.1(3) . . ? C13 C12 C1 121.3(3) . . ? C14 C13 C12 119.2(4) . . ? C15 C14 C13 118.7(4) . . ? C16 C15 C14 119.8(4) . . ? N11 C16 C15 121.8(4) . . ? 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 N6 Cu1 N2 C3 -12.1(3) . . . . ? N11 Cu1 N2 C3 174.6(3) . . . . ? Cl1 Cu1 N2 C3 -105.7(4) . . . . ? Cl2 Cu1 N2 C3 86.4(3) . . . . ? N6 Cu1 N2 C1 177.4(3) . . . . ? N11 Cu1 N2 C1 4.1(2) . . . . ? Cl1 Cu1 N2 C1 83.8(4) . . . . ? Cl2 Cu1 N2 C1 -84.2(2) . . . . ? C3 N2 C1 C12 -176.6(3) . . . . ? Cu1 N2 C1 C12 -4.9(4) . . . . ? C1 N2 C3 N31 -2.0(5) . . . . ? Cu1 N2 C3 N31 -172.5(3) . . . . ? C1 N2 C3 N4 177.6(3) . . . . ? Cu1 N2 C3 N4 7.1(5) . . . . ? N2 C3 N4 C5 3.7(6) . . . . ? N31 C3 N4 C5 -176.7(3) . . . . ? C3 N4 C5 N6 -4.3(6) . . . . ? C3 N4 C5 O51 175.3(3) . . . . ? N6 C5 O51 C52 -6.5(6) . . . . ? N4 C5 O51 C52 174.0(3) . . . . ? C5 O51 C52 C53 -176.1(3) . . . . ? O51 C5 N6 Cu1 174.4(3) . . . . ? N4 C5 N6 Cu1 -6.2(6) . . . . ? N2 Cu1 N6 C5 11.6(4) . . . . ? N11 Cu1 N6 C5 50.4(9) . . . . ? Cl1 Cu1 N6 C5 176.3(3) . . . . ? Cl2 Cu1 N6 C5 -82.9(3) . . . . ? N6 Cu1 N11 C12 -41.6(8) . . . . ? N2 Cu1 N11 C12 -2.4(3) . . . . ? Cl1 Cu1 N11 C12 -167.2(2) . . . . ? Cl2 Cu1 N11 C12 92.3(3) . . . . ? N6 Cu1 N11 C16 140.6(6) . . . . ? N2 Cu1 N11 C16 179.8(3) . . . . ? Cl1 Cu1 N11 C16 15.1(3) . . . . ? Cl2 Cu1 N11 C16 -85.4(3) . . . . ? C16 N11 C12 C13 -1.1(5) . . . . ? Cu1 N11 C12 C13 -179.0(3) . . . . ? C16 N11 C12 C1 178.2(3) . . . . ? Cu1 N11 C12 C1 0.2(4) . . . . ? N2 C1 C12 N11 3.0(5) . . . . ? N2 C1 C12 C13 -177.8(3) . . . . ? N11 C12 C13 C14 1.8(6) . . . . ? C1 C12 C13 C14 -177.4(4) . . . . ? C12 C13 C14 C15 -0.9(6) . . . . ? C13 C14 C15 C16 -0.6(6) . . . . ? C12 N11 C16 C15 -0.5(6) . . . . ? Cu1 N11 C16 C15 177.2(3) . . . . ? C14 C15 C16 N11 1.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.727 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.117 data_CUPYIM _database_code_depnum_ccdc_archive 'CCDC 236516' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H17 Cl2 Cu N5 O2' _chemical_formula_weight 373.73 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 P2(1)/n 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 11.810(2) _cell_length_b 8.2394(12) _cell_length_c 16.073(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.282(3) _cell_angle_gamma 90.00 _cell_volume 1515.6(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2489 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.4 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 1.801 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.461 _exptl_absorpt_correction_T_max 0.756 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 6978 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.43 _reflns_number_total 3548 _reflns_number_gt 2400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2000)' _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^)+(0.0507P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'difference Fourier' _atom_sites_solution_hydrogens ; C-H placed geometrically, N-H and O-H located by deltaF ; _refine_ls_hydrogen_treatment ; C-H riding on parent atom, N-H and O-H refined with restraints ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3326 _refine_ls_number_parameters 200 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0575 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.936 _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 Cu Cu 0.30265(3) 0.40543(4) 0.40883(2) 0.01886(12) Uani 1 1 d . . . C100 C 0.4396(2) 0.3209(4) 0.58171(18) 0.0215(6) Uani 1 1 d . . . H10A H 0.4166 0.2349 0.6154 0.026 Uiso 1 1 calc R . . H10B H 0.4923 0.3932 0.6206 0.026 Uiso 1 1 calc R . . N101 N 0.33595(19) 0.4109(3) 0.53563(15) 0.0184(5) Uani 1 1 d . . . C102 C 0.2746(2) 0.4792(4) 0.58341(18) 0.0194(6) Uani 1 1 d . . . N103 N 0.1770(2) 0.5745(3) 0.54732(16) 0.0224(6) Uani 1 1 d D . . H103 H 0.144(3) 0.628(3) 0.5816(16) 0.027 Uiso 1 1 d D . . C104 C 0.1358(2) 0.6173(4) 0.46328(19) 0.0219(6) Uani 1 1 d . . . N105 N 0.1763(2) 0.5638(3) 0.40162(16) 0.0234(6) Uani 1 1 d D . . H105 H 0.140(2) 0.602(4) 0.3519(11) 0.028 Uiso 1 1 d D . . N121 N 0.2985(2) 0.4702(3) 0.66942(16) 0.0268(6) Uani 1 1 d D . . H12A H 0.340(3) 0.390(3) 0.6977(19) 0.032 Uiso 1 1 d D . . H12B H 0.251(2) 0.514(4) 0.6964(19) 0.032 Uiso 1 1 d D . . O141 O 0.04833(18) 0.7248(3) 0.45837(13) 0.0281(5) Uani 1 1 d . . . C142 C -0.0162(3) 0.7847(4) 0.37468(19) 0.0264(7) Uani 1 1 d . . . H14A H -0.0507 0.6954 0.3377 0.032 Uiso 1 1 calc R . . H14B H 0.0349 0.8449 0.3470 0.032 Uiso 1 1 calc R . . C143 C -0.1102(3) 0.8941(4) 0.3927(2) 0.0321(8) Uani 1 1 d . . . H14C H -0.1524 0.8373 0.4277 0.048 Uiso 1 1 calc R . . H14D H -0.1631 0.9249 0.3396 0.048 Uiso 1 1 calc R . . H14E H -0.0749 0.9895 0.4224 0.048 Uiso 1 1 calc R . . N201 N 0.4512(2) 0.2725(3) 0.43449(15) 0.0195(5) Uani 1 1 d . . . C211 C 0.5012(2) 0.2489(3) 0.51822(18) 0.0183(6) Uani 1 1 d . . . C212 C 0.6051(3) 0.1611(4) 0.5470(2) 0.0242(7) Uani 1 1 d . . . H212 H 0.6382 0.1473 0.6054 0.029 Uiso 1 1 calc R . . C213 C 0.6575(3) 0.0950(4) 0.4861(2) 0.0263(7) Uani 1 1 d . . . H213 H 0.7266 0.0361 0.5033 0.032 Uiso 1 1 calc R . . C214 C 0.6059(3) 0.1177(4) 0.3997(2) 0.0260(7) Uani 1 1 d . . . H214 H 0.6396 0.0738 0.3582 0.031 Uiso 1 1 calc R . . C215 C 0.5033(3) 0.2067(4) 0.3757(2) 0.0253(7) Uani 1 1 d . . . H215 H 0.4690 0.2219 0.3176 0.030 Uiso 1 1 calc R . . Cl1 Cl 0.29553(7) 0.44112(10) 0.26517(5) 0.02731(19) Uani 1 1 d . . . Cl2 Cl 0.07892(6) 0.66595(10) 0.70847(5) 0.02628(18) Uani 1 1 d . . . O1W O 0.17291(18) 0.1838(3) 0.38416(14) 0.0261(5) Uani 1 1 d D . . H1WA H 0.179(3) 0.128(4) 0.3437(16) 0.039 Uiso 1 1 d D . . H1WB H 0.1091(17) 0.229(4) 0.366(2) 0.039 Uiso 1 1 d 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 Cu 0.01814(19) 0.0255(2) 0.01423(19) 0.00062(15) 0.00635(14) 0.00187(15) C100 0.0217(15) 0.0272(17) 0.0169(15) 0.0013(12) 0.0075(12) 0.0008(12) N101 0.0151(11) 0.0246(13) 0.0161(12) 0.0013(10) 0.0053(10) 0.0017(10) C102 0.0197(15) 0.0222(15) 0.0173(15) 0.0017(12) 0.0067(12) -0.0018(12) N103 0.0216(13) 0.0305(15) 0.0174(13) -0.0013(11) 0.0094(10) 0.0078(11) C104 0.0178(14) 0.0235(16) 0.0238(16) -0.0007(12) 0.0041(12) -0.0002(12) N105 0.0225(13) 0.0338(16) 0.0133(12) -0.0007(11) 0.0029(10) 0.0065(11) N121 0.0299(15) 0.0367(16) 0.0159(13) 0.0018(12) 0.0093(11) 0.0129(12) O141 0.0300(12) 0.0369(13) 0.0188(11) 0.0020(9) 0.0086(9) 0.0159(10) C142 0.0267(16) 0.0338(18) 0.0189(15) 0.0028(13) 0.0061(13) 0.0046(14) C143 0.0299(17) 0.039(2) 0.0262(17) 0.0065(15) 0.0051(14) 0.0138(15) N201 0.0193(12) 0.0253(13) 0.0170(12) 0.0019(10) 0.0101(10) -0.0005(10) C211 0.0188(14) 0.0169(14) 0.0203(15) -0.0005(11) 0.0068(12) -0.0029(11) C212 0.0209(15) 0.0297(17) 0.0220(16) 0.0030(13) 0.0055(13) -0.0033(13) C213 0.0199(15) 0.0256(16) 0.0362(19) 0.0018(14) 0.0122(14) 0.0031(13) C214 0.0258(15) 0.0307(18) 0.0260(17) -0.0011(14) 0.0152(13) 0.0020(13) C215 0.0295(17) 0.0298(17) 0.0195(15) -0.0006(13) 0.0117(13) 0.0017(13) Cl1 0.0295(4) 0.0382(5) 0.0162(4) 0.0044(3) 0.0092(3) 0.0036(3) Cl2 0.0236(4) 0.0359(4) 0.0211(4) -0.0057(3) 0.0088(3) 0.0026(3) O1W 0.0242(11) 0.0314(13) 0.0232(12) -0.0043(10) 0.0069(10) 0.0023(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N105 1.964(2) . y Cu N101 1.979(2) . y Cu N201 2.022(2) . y Cu Cl1 2.3086(8) . y Cu O1W 2.354(2) . y C100 N101 1.466(3) . ? C100 C211 1.512(4) . ? C100 H10A 0.9700 . ? C100 H10B 0.9700 . ? N101 C102 1.306(4) . ? C102 N121 1.343(4) . ? C102 N103 1.396(4) . ? N103 C104 1.364(4) . ? N103 H103 0.868(10) . ? C104 N105 1.280(4) . ? C104 O141 1.348(3) . ? N105 H105 0.868(10) . ? N121 H12A 0.875(10) . ? N121 H12B 0.868(10) . ? O141 C142 1.459(3) . ? C142 C143 1.513(4) . ? C142 H14A 0.9700 . ? C142 H14B 0.9700 . ? C143 H14C 0.9600 . ? C143 H14D 0.9600 . ? C143 H14E 0.9600 . ? N201 C211 1.344(4) . ? N201 C215 1.361(4) . ? C211 C212 1.402(4) . ? C212 C213 1.392(4) . ? C212 H212 0.9300 . ? C213 C214 1.385(4) . ? C213 H213 0.9300 . ? C214 C215 1.387(4) . ? C214 H214 0.9300 . ? C215 H215 0.9300 . ? O1W H1WA 0.813(10) . ? O1W H1WB 0.824(10) . ? 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 N105 Cu N101 90.04(10) . . y N105 Cu N201 168.52(10) . . y N101 Cu N201 81.97(9) . . y N105 Cu Cl1 90.96(8) . . y N101 Cu Cl1 167.49(7) . . y N201 Cu Cl1 95.09(7) . . y N105 Cu O1W 92.99(9) . . y N101 Cu O1W 98.45(9) . . y N201 Cu O1W 96.31(9) . . y Cl1 Cu O1W 93.95(6) . . y N101 C100 C211 109.8(2) . . ? N101 C100 H10A 109.7 . . ? C211 C100 H10A 109.7 . . ? N101 C100 H10B 109.7 . . ? C211 C100 H10B 109.7 . . ? H10A C100 H10B 108.2 . . ? C102 N101 C100 115.9(2) . . ? C102 N101 Cu 128.12(19) . . ? C100 N101 Cu 115.96(17) . . ? N101 C102 N121 125.1(3) . . ? N101 C102 N103 121.2(3) . . ? N121 C102 N103 113.6(3) . . ? C104 N103 C102 127.8(3) . . ? C104 N103 H103 113(2) . . ? C102 N103 H103 118(2) . . ? N105 C104 O141 127.4(3) . . ? N105 C104 N103 124.6(3) . . ? O141 C104 N103 108.0(2) . . ? C104 N105 Cu 127.3(2) . . ? C104 N105 H105 113(2) . . ? Cu N105 H105 119(2) . . ? C102 N121 H12A 122(2) . . ? C102 N121 H12B 120(2) . . ? H12A N121 H12B 113(3) . . ? C104 O141 C142 119.7(2) . . ? O141 C142 C143 105.4(2) . . ? O141 C142 H14A 110.7 . . ? C143 C142 H14A 110.7 . . ? O141 C142 H14B 110.7 . . ? C143 C142 H14B 110.7 . . ? H14A C142 H14B 108.8 . . ? C142 C143 H14C 109.5 . . ? C142 C143 H14D 109.5 . . ? H14C C143 H14D 109.5 . . ? C142 C143 H14E 109.5 . . ? H14C C143 H14E 109.5 . . ? H14D C143 H14E 109.5 . . ? C211 N201 C215 118.4(3) . . ? C211 N201 Cu 115.31(19) . . ? C215 N201 Cu 126.3(2) . . ? N201 C211 C212 122.6(3) . . ? N201 C211 C100 117.0(2) . . ? C212 C211 C100 120.5(3) . . ? C213 C212 C211 118.4(3) . . ? C213 C212 H212 120.8 . . ? C211 C212 H212 120.8 . . ? C214 C213 C212 119.3(3) . . ? C214 C213 H213 120.3 . . ? C212 C213 H213 120.3 . . ? C213 C214 C215 119.3(3) . . ? C213 C214 H214 120.4 . . ? C215 C214 H214 120.4 . . ? N201 C215 C214 122.1(3) . . ? N201 C215 H215 118.9 . . ? C214 C215 H215 118.9 . . ? Cu O1W H1WA 113(3) . . ? Cu O1W H1WB 102(3) . . ? H1WA O1W H1WB 103(3) . . ? 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 C211 C100 N101 C102 179.9(2) . . . . ? C211 C100 N101 Cu 2.6(3) . . . . ? N105 Cu N101 C102 9.7(3) . . . . ? N201 Cu N101 C102 -178.6(3) . . . . ? Cl1 Cu N101 C102 104.3(4) . . . . ? O1W Cu N101 C102 -83.3(3) . . . . ? N105 Cu N101 C100 -173.4(2) . . . . ? N201 Cu N101 C100 -1.63(19) . . . . ? Cl1 Cu N101 C100 -78.8(4) . . . . ? O1W Cu N101 C100 93.61(19) . . . . ? C100 N101 C102 N121 -1.1(4) . . . . ? Cu N101 C102 N121 175.8(2) . . . . ? C100 N101 C102 N103 177.0(3) . . . . ? Cu N101 C102 N103 -6.1(4) . . . . ? N101 C102 N103 C104 -3.8(5) . . . . ? N121 C102 N103 C104 174.6(3) . . . . ? C102 N103 C104 N105 6.2(5) . . . . ? C102 N103 C104 O141 -173.0(3) . . . . ? O141 C104 N105 Cu -179.3(2) . . . . ? N103 C104 N105 Cu 1.7(5) . . . . ? N101 Cu N105 C104 -7.5(3) . . . . ? N201 Cu N105 C104 -53.1(7) . . . . ? Cl1 Cu N105 C104 -175.0(3) . . . . ? O1W Cu N105 C104 91.0(3) . . . . ? N105 C104 O141 C142 4.1(5) . . . . ? N103 C104 O141 C142 -176.7(2) . . . . ? C104 O141 C142 C143 177.1(3) . . . . ? N105 Cu N201 C211 46.4(6) . . . . ? N101 Cu N201 C211 0.2(2) . . . . ? Cl1 Cu N201 C211 167.98(19) . . . . ? O1W Cu N201 C211 -97.5(2) . . . . ? N105 Cu N201 C215 -133.5(5) . . . . ? N101 Cu N201 C215 -179.8(3) . . . . ? Cl1 Cu N201 C215 -12.0(2) . . . . ? O1W Cu N201 C215 82.5(2) . . . . ? C215 N201 C211 C212 0.7(4) . . . . ? Cu N201 C211 C212 -179.3(2) . . . . ? C215 N201 C211 C100 -178.8(3) . . . . ? Cu N201 C211 C100 1.2(3) . . . . ? N101 C100 C211 N201 -2.4(4) . . . . ? N101 C100 C211 C212 178.1(2) . . . . ? N201 C211 C212 C213 -0.5(4) . . . . ? C100 C211 C212 C213 179.0(3) . . . . ? C211 C212 C213 C214 -0.1(4) . . . . ? C212 C213 C214 C215 0.4(5) . . . . ? C211 N201 C215 C214 -0.4(4) . . . . ? Cu N201 C215 C214 179.6(2) . . . . ? C213 C214 C215 N201 -0.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.678 _refine_diff_density_min -0.867 _refine_diff_density_rms 0.095 data_CUCLN3 _database_code_depnum_ccdc_archive 'CCDC 236517' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H13 Cl2 Cu N5 O' _chemical_formula_weight 341.68 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 P2(1)/n 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 11.4766(11) _cell_length_b 8.7847(8) _cell_length_c 13.5378(12) _cell_angle_alpha 90.00 _cell_angle_beta 109.089(1) _cell_angle_gamma 90.00 _cell_volume 1289.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4002 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 28.79 _exptl_crystal_description 'Irregular plate' _exptl_crystal_colour Blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.760 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 2.102 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.672 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 9284 _diffrn_reflns_av_R_equivalents 0.034 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.89 _reflns_number_total 3237 _reflns_number_gt 2425 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2001)' _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^)+(0.0684P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'difference Fourier' _atom_sites_solution_hydrogens 'placed geometrically' _refine_ls_hydrogen_treatment 'riding on parent atom' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3044 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.1021 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 Cu Cu 0.75631(3) 0.19190(4) 0.04863(2) 0.01896(12) Uani 1 1 d . . . C100 C 0.9974(3) 0.2914(3) 0.1821(2) 0.0233(6) Uani 1 1 d . . . H10A H 1.0542 0.3278 0.1458 0.028 Uiso 1 1 calc R . . H10B H 1.0469 0.2647 0.2547 0.028 Uiso 1 1 calc R . . N101 N 0.9314(2) 0.1575(3) 0.12894(17) 0.0190(5) Uani 1 1 d . . . C102 C 0.9965(2) 0.0366(3) 0.13188(19) 0.0176(5) Uani 1 1 d . . . N103 N 0.9450(2) -0.0956(3) 0.07884(17) 0.0197(5) Uani 1 1 d . . . H103 H 0.9963 -0.1715 0.0824 0.024 Uiso 1 1 calc R . . C104 C 0.8244(2) -0.1219(3) 0.02187(19) 0.0184(5) Uani 1 1 d . . . N105 N 0.7386(2) -0.0228(3) 0.00827(18) 0.0216(5) Uani 1 1 d . . . H105 H 0.6629 -0.0551 -0.0229 0.026 Uiso 1 1 calc R . . N121 N 1.1184(2) 0.0239(3) 0.18240(17) 0.0225(5) Uani 1 1 d . . . H12A H 1.1601 0.1020 0.2171 0.027 Uiso 1 1 calc R . . H12B H 1.1563 -0.0627 0.1807 0.027 Uiso 1 1 calc R . . O141 O 0.81383(18) -0.2641(2) -0.01341(14) 0.0218(4) Uani 1 1 d . . . C142 C 0.6964(3) -0.3111(3) -0.0871(2) 0.0239(6) Uani 1 1 d . . . H14A H 0.7015 -0.4176 -0.1067 0.036 Uiso 1 1 calc R . . H14B H 0.6764 -0.2469 -0.1497 0.036 Uiso 1 1 calc R . . H14C H 0.6319 -0.3004 -0.0548 0.036 Uiso 1 1 calc R . . N201 N 0.7885(2) 0.3916(2) 0.12575(16) 0.0187(5) Uani 1 1 d . . . C211 C 0.9076(2) 0.4150(3) 0.18300(19) 0.0194(5) Uani 1 1 d . . . C212 C 0.9465(3) 0.5461(3) 0.2419(2) 0.0237(6) Uani 1 1 d . . . H212 H 1.0311 0.5599 0.2812 0.028 Uiso 1 1 calc R . . C213 C 0.8609(3) 0.6561(3) 0.2425(2) 0.0262(6) Uani 1 1 d . . . H213 H 0.8856 0.7467 0.2821 0.031 Uiso 1 1 calc R . . C214 C 0.7379(3) 0.6322(3) 0.1841(2) 0.0251(6) Uani 1 1 d . . . H214 H 0.6771 0.7060 0.1835 0.030 Uiso 1 1 calc R . . C215 C 0.7055(2) 0.4998(3) 0.1270(2) 0.0214(5) Uani 1 1 d . . . H215 H 0.6213 0.4841 0.0870 0.026 Uiso 1 1 calc R . . Cl1 Cl 0.55022(6) 0.22689(8) -0.02699(5) 0.02728(18) Uani 1 1 d . . . Cl2 Cl 0.82047(6) 0.31071(8) -0.12209(5) 0.02409(16) 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 Cu 0.01746(19) 0.02030(19) 0.01853(18) -0.00326(12) 0.00507(13) 0.00307(12) C100 0.0213(14) 0.0263(15) 0.0225(13) -0.0049(11) 0.0076(11) 0.0014(11) N101 0.0184(11) 0.0216(11) 0.0171(10) -0.0022(9) 0.0058(9) 0.0016(9) C102 0.0209(13) 0.0218(13) 0.0118(11) 0.0013(9) 0.0077(10) 0.0007(10) N103 0.0194(11) 0.0188(11) 0.0212(11) -0.0006(9) 0.0072(9) 0.0048(9) C104 0.0227(13) 0.0209(13) 0.0133(11) 0.0016(9) 0.0083(10) 0.0002(10) N105 0.0178(11) 0.0237(12) 0.0224(11) -0.0051(9) 0.0051(9) 0.0002(9) N121 0.0217(12) 0.0207(12) 0.0231(11) -0.0044(9) 0.0046(9) 0.0045(9) O141 0.0225(10) 0.0195(9) 0.0224(9) -0.0021(7) 0.0060(8) 0.0046(8) C142 0.0249(14) 0.0224(14) 0.0241(14) -0.0058(11) 0.0074(11) -0.0007(11) N201 0.0239(11) 0.0200(11) 0.0148(10) -0.0002(8) 0.0099(9) 0.0015(9) C211 0.0243(14) 0.0211(13) 0.0150(12) 0.0003(10) 0.0094(10) 0.0030(11) C212 0.0242(14) 0.0235(14) 0.0229(13) -0.0046(11) 0.0068(11) -0.0010(11) C213 0.0337(16) 0.0242(14) 0.0229(14) -0.0056(11) 0.0123(12) 0.0010(12) C214 0.0321(16) 0.0222(14) 0.0238(14) -0.0011(11) 0.0128(12) 0.0047(12) C215 0.0210(13) 0.0249(14) 0.0199(12) 0.0007(10) 0.0088(11) 0.0026(11) Cl1 0.0190(3) 0.0325(4) 0.0284(4) -0.0053(3) 0.0051(3) 0.0054(3) Cl2 0.0262(3) 0.0245(3) 0.0219(3) 0.0014(2) 0.0083(3) 0.0084(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu N105 1.955(2) . y Cu N101 1.970(2) . y Cu N201 2.013(2) . y Cu Cl1 2.2701(8) . y C100 N101 1.456(3) . ? C100 C211 1.500(4) . ? C100 H10A 0.9900 . ? C100 H10B 0.9900 . ? N101 C102 1.291(3) . ? C102 N121 1.346(3) . ? C102 N103 1.392(3) . ? N103 C104 1.366(3) . ? N103 H103 0.8800 . ? C104 N105 1.282(3) . ? C104 O141 1.329(3) . ? N105 H105 0.8800 . ? N121 H12A 0.8800 . ? N121 H12B 0.8800 . ? O141 C142 1.450(3) . ? C142 H14A 0.9800 . ? C142 H14B 0.9800 . ? C142 H14C 0.9800 . ? N201 C211 1.348(3) . ? N201 C215 1.350(3) . ? C211 C212 1.388(4) . ? C212 C213 1.380(4) . ? C212 H212 0.9500 . ? C213 C214 1.390(4) . ? C213 H213 0.9500 . ? C214 C215 1.379(4) . ? C214 H214 0.9500 . ? C215 H215 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 N105 Cu N101 90.01(9) . . y N105 Cu N201 165.97(9) . . y N101 Cu N201 82.34(9) . . y N105 Cu Cl1 90.39(7) . . y N101 Cu Cl1 173.60(7) . . y N201 Cu Cl1 95.92(7) . . y N101 C100 C211 110.0(2) . . ? N101 C100 H10A 109.7 . . ? C211 C100 H10A 109.7 . . ? N101 C100 H10B 109.7 . . ? C211 C100 H10B 109.7 . . ? H10A C100 H10B 108.2 . . ? C102 N101 C100 116.5(2) . . ? C102 N101 Cu 128.23(19) . . ? C100 N101 Cu 114.86(17) . . ? N101 C102 N121 125.4(2) . . ? N101 C102 N103 121.7(2) . . ? N121 C102 N103 112.9(2) . . ? C104 N103 C102 127.9(2) . . ? C104 N103 H103 116.1 . . ? C102 N103 H103 116.1 . . ? N105 C104 O141 127.7(2) . . ? N105 C104 N103 123.7(2) . . ? O141 C104 N103 108.6(2) . . ? C104 N105 Cu 127.63(19) . . ? C104 N105 H105 116.2 . . ? Cu N105 H105 116.2 . . ? C102 N121 H12A 120.0 . . ? C102 N121 H12B 120.0 . . ? H12A N121 H12B 120.0 . . ? C104 O141 C142 118.0(2) . . ? O141 C142 H14A 109.5 . . ? O141 C142 H14B 109.5 . . ? H14A C142 H14B 109.5 . . ? O141 C142 H14C 109.5 . . ? H14A C142 H14C 109.5 . . ? H14B C142 H14C 109.5 . . ? C211 N201 C215 118.2(2) . . ? C211 N201 Cu 114.23(17) . . ? C215 N201 Cu 127.56(18) . . ? N201 C211 C212 122.1(2) . . ? N201 C211 C100 117.1(2) . . ? C212 C211 C100 120.8(2) . . ? C213 C212 C211 119.2(3) . . ? C213 C212 H212 120.4 . . ? C211 C212 H212 120.4 . . ? C212 C213 C214 118.9(3) . . ? C212 C213 H213 120.5 . . ? C214 C213 H213 120.5 . . ? C215 C214 C213 118.9(3) . . ? C215 C214 H214 120.5 . . ? C213 C214 H214 120.5 . . ? N201 C215 C214 122.6(2) . . ? N201 C215 H215 118.7 . . ? C214 C215 H215 118.7 . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.090 _refine_diff_density_min -0.891 _refine_diff_density_rms 0.147