# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_cho092p4nmm _database_code_depnum_ccdc_archive 'CCDC 729199' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 Cl2 N5 Ni O8' _chemical_formula_weight 507.81 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4/nmm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, y+1/2, -z' 'x+1/2, -y, -z' 'y+1/2, x+1/2, -z' '-y, -x, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' 'x, -y-1/2, z' '-x-1/2, y, z' '-y-1/2, -x-1/2, z' 'y, x, z' _cell_length_a 9.2584(6) _cell_length_b 9.2584(6) _cell_length_c 14.1473(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1212.68(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1470 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 20.00 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 502 _exptl_absorpt_coefficient_mu 1.065 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7472 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0542 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 28.24 _reflns_number_total 912 _reflns_number_gt 565 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1030P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens ? _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 912 _refine_ls_number_parameters 75 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1651 _refine_ls_wR_factor_gt 0.1594 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 Ni1 Ni 0.2500 0.2500 0.75269(7) 0.0423(4) Uani 1 8 d S . . Cl1 Cl 0.2500 0.2500 0.11623(17) 0.0618(7) Uani 1 8 d S . . Cl2 Cl 0.7500 0.2500 0.5000 0.0878(10) Uani 1 8 d S . . N2 N 0.2500 0.2500 0.6121(6) 0.068(2) Uani 1 8 d S . . N1 N 0.4058(3) 0.0942(3) 0.7821(3) 0.0736(13) Uani 1 2 d S . . C5 C 0.2500 0.2500 0.5352(8) 0.079(3) Uani 1 8 d S . . C4 C 0.4754(5) 0.0246(5) 0.7002(6) 0.112(2) Uani 1 2 d S . . O2 O 0.2500 0.2500 0.2120(9) 0.170(6) Uani 1 8 d S . . O1 O 0.2500 0.1064(10) 0.0843(7) 0.187(4) Uani 0.75 2 d SP . . C2 C 0.377(2) 0.0342(18) 0.8677(13) 0.075(5) Uani 0.25 1 d P . . O3 O 0.7500 0.0923(17) 0.5084(12) 0.216(9) Uani 0.50 2 d SP . . C1 C 0.3170(12) -0.0330(10) 0.8251(8) 0.165(5) Uani 0.75 1 d P . . O4 O 0.6836(19) 0.2500 0.4195(10) 0.201(11) Uani 0.50 2 d SP . . C6 C 0.2500 0.2500 0.4260(8) 0.126(6) Uani 1 8 d S . . C3 C 0.2500 -0.052(4) 0.8741(19) 0.088(8) Uani 0.25 2 d SP . . 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 Ni1 0.0410(5) 0.0410(5) 0.0450(7) 0.000 0.000 0.000 Cl1 0.0675(10) 0.0675(10) 0.0504(13) 0.000 0.000 0.000 Cl2 0.1017(16) 0.1017(16) 0.0602(19) 0.000 0.000 0.000 N2 0.079(4) 0.079(4) 0.046(5) 0.000 0.000 0.000 N1 0.0703(19) 0.0703(19) 0.080(3) 0.0019(15) -0.0019(15) 0.030(2) C5 0.090(5) 0.090(5) 0.057(7) 0.000 0.000 0.000 C4 0.113(4) 0.113(4) 0.110(5) -0.014(3) 0.014(3) 0.058(5) O2 0.214(10) 0.214(10) 0.084(7) 0.000 0.000 0.000 O1 0.212(9) 0.127(7) 0.221(9) -0.079(6) 0.000 0.000 C2 0.072(11) 0.066(11) 0.086(11) 0.042(8) 0.012(8) 0.025(9) O3 0.39(3) 0.105(10) 0.155(13) -0.001(10) 0.000 0.000 C1 0.141(11) 0.095(7) 0.260(15) 0.088(9) 0.061(9) 0.036(5) O4 0.26(3) 0.160(11) 0.180(12) 0.000 -0.152(17) 0.000 C6 0.166(10) 0.166(10) 0.045(7) 0.000 0.000 0.000 C3 0.10(2) 0.09(2) 0.072(16) 0.027(14) 0.000 0.000 _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 Ni1 N2 1.989(8) . ? Ni1 N1 2.082(4) . ? Ni1 N1 2.082(4) 3 ? Ni1 N1 2.082(4) 2 ? Ni1 N1 2.082(4) 4 ? Cl1 O2 1.355(12) . ? Cl1 O1 1.404(8) 2 ? Cl1 O1 1.404(8) 4 ? Cl1 O1 1.404(8) 3 ? Cl1 O1 1.404(8) . ? Cl2 O4 1.295(11) . ? Cl2 O4 1.295(11) 2_655 ? Cl2 O4 1.295(11) 11_666 ? Cl2 O4 1.295(11) 12_656 ? Cl2 O3 1.465(15) 11_666 ? Cl2 O3 1.465(15) 12_656 ? Cl2 O3 1.465(15) . ? Cl2 O3 1.465(15) 2_655 ? N2 C5 1.089(12) . ? N1 C2 1.359(18) 15_665 ? N1 C2 1.359(18) . ? N1 C4 1.475(8) . ? N1 C1 1.560(9) 15_665 ? N1 C1 1.560(9) . ? C5 C6 1.545(15) . ? C2 C1 1.03(2) . ? C2 C2 1.17(4) 15_665 ? C2 C3 1.42(3) . ? C2 C1 1.991(18) 14_655 ? O3 O4 1.325(17) 12_656 ? C1 C3 0.95(2) . ? C1 C1 1.24(2) 14_655 ? C1 C2 1.991(18) 14_655 ? O4 O4 1.23(4) 2_655 ? O4 O3 1.325(17) 11_666 ? C3 C1 0.95(2) 14_655 ? C3 C2 1.42(3) 14_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ni1 N1 101.54(13) . . ? N2 Ni1 N1 101.54(13) . 3 ? N1 Ni1 N1 87.71(5) . 3 ? N2 Ni1 N1 101.54(13) . 2 ? N1 Ni1 N1 156.9(3) . 2 ? N1 Ni1 N1 87.71(5) 3 2 ? N2 Ni1 N1 101.54(13) . 4 ? N1 Ni1 N1 87.71(5) . 4 ? N1 Ni1 N1 156.9(3) 3 4 ? N1 Ni1 N1 87.71(5) 2 4 ? O2 Cl1 O1 108.8(5) . 2 ? O2 Cl1 O1 108.8(5) . 4 ? O1 Cl1 O1 84.1(3) 2 4 ? O2 Cl1 O1 108.8(5) . 3 ? O1 Cl1 O1 84.1(3) 2 3 ? O1 Cl1 O1 142.5(10) 4 3 ? O2 Cl1 O1 108.8(5) . . ? O1 Cl1 O1 142.5(10) 2 . ? O1 Cl1 O1 84.1(3) 4 . ? O1 Cl1 O1 84.1(3) 3 . ? O4 Cl2 O4 56.7(18) . 2_655 ? O4 Cl2 O4 140.8(12) . 11_666 ? O4 Cl2 O4 140.8(12) 2_655 11_666 ? O4 Cl2 O4 140.8(12) . 12_656 ? O4 Cl2 O4 140.8(12) 2_655 12_656 ? O4 Cl2 O4 56.7(18) 11_666 12_656 ? O4 Cl2 O3 57.0(8) . 11_666 ? O4 Cl2 O3 113.7(14) 2_655 11_666 ? O4 Cl2 O3 94.1(6) 11_666 11_666 ? O4 Cl2 O3 94.1(6) 12_656 11_666 ? O4 Cl2 O3 113.7(14) . 12_656 ? O4 Cl2 O3 57.0(8) 2_655 12_656 ? O4 Cl2 O3 94.1(6) 11_666 12_656 ? O4 Cl2 O3 94.1(6) 12_656 12_656 ? O3 Cl2 O3 170.7(13) 11_666 12_656 ? O4 Cl2 O3 94.1(6) . . ? O4 Cl2 O3 94.1(6) 2_655 . ? O4 Cl2 O3 113.7(14) 11_666 . ? O4 Cl2 O3 57.0(8) 12_656 . ? O3 Cl2 O3 90.38(11) 11_666 . ? O3 Cl2 O3 90.38(11) 12_656 . ? O4 Cl2 O3 94.1(6) . 2_655 ? O4 Cl2 O3 94.1(6) 2_655 2_655 ? O4 Cl2 O3 57.0(8) 11_666 2_655 ? O4 Cl2 O3 113.7(14) 12_656 2_655 ? O3 Cl2 O3 90.38(11) 11_666 2_655 ? O3 Cl2 O3 90.38(11) 12_656 2_655 ? O3 Cl2 O3 170.7(13) . 2_655 ? C5 N2 Ni1 180.000(2) . . ? C2 N1 C2 50.9(15) 15_665 . ? C2 N1 C4 127.5(8) 15_665 . ? C2 N1 C4 127.5(8) . . ? C2 N1 C1 40.5(8) 15_665 15_665 ? C2 N1 C1 91.1(10) . 15_665 ? C4 N1 C1 101.9(5) . 15_665 ? C2 N1 C1 91.1(10) 15_665 . ? C2 N1 C1 40.5(8) . . ? C4 N1 C1 101.9(5) . . ? C1 N1 C1 130.1(10) 15_665 . ? C2 N1 Ni1 108.9(9) 15_665 . ? C2 N1 Ni1 108.9(9) . . ? C4 N1 Ni1 116.6(4) . . ? C1 N1 Ni1 103.6(4) 15_665 . ? C1 N1 Ni1 103.6(4) . . ? N2 C5 C6 180.000(4) . . ? C1 C2 C2 143.9(15) . 15_665 ? C1 C2 N1 80.3(15) . . ? C2 C2 N1 64.6(8) 15_665 . ? C1 C2 C3 41.7(17) . . ? C2 C2 C3 168.6(13) 15_665 . ? N1 C2 C3 116.7(17) . . ? C1 C2 C1 31.7(11) . 14_655 ? C2 C2 C1 149.1(6) 15_665 14_655 ? N1 C2 C1 92.1(10) . 14_655 ? C3 C2 C1 26.0(11) . 14_655 ? O4 O3 Cl2 55.0(8) 12_656 . ? C3 C1 C2 92(3) . . ? C3 C1 C1 49.1(14) . 14_655 ? C2 C1 C1 122.5(16) . 14_655 ? C3 C1 N1 140(3) . . ? C2 C1 N1 59.2(12) . . ? C1 C1 N1 121.8(4) 14_655 . ? C3 C1 C2 41.1(17) . 14_655 ? C2 C1 C2 97(2) . 14_655 ? C1 C1 C2 25.8(7) 14_655 14_655 ? N1 C1 C2 110.9(8) . 14_655 ? O4 O4 Cl2 61.6(9) 2_655 . ? O4 O4 O3 129.7(10) 2_655 11_666 ? Cl2 O4 O3 68.0(10) . 11_666 ? C1 C3 C1 82(3) . 14_655 ? C1 C3 C2 113(3) . 14_655 ? C1 C3 C2 46.3(15) 14_655 14_655 ? C1 C3 C2 46.3(15) . . ? C1 C3 C2 113(3) 14_655 . ? C2 C3 C2 111(2) 14_655 . ? 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 N1 Ni1 N2 C5 33(100) . . . . ? N1 Ni1 N2 C5 123(100) 3 . . . ? N1 Ni1 N2 C5 -147(100) 2 . . . ? N1 Ni1 N2 C5 -57(100) 4 . . . ? N2 Ni1 N1 C2 153.0(8) . . . 15_665 ? N1 Ni1 N1 C2 51.7(9) 3 . . 15_665 ? N1 Ni1 N1 C2 -27.0(8) 2 . . 15_665 ? N1 Ni1 N1 C2 -105.7(8) 4 . . 15_665 ? N2 Ni1 N1 C2 -153.0(8) . . . . ? N1 Ni1 N1 C2 105.7(8) 3 . . . ? N1 Ni1 N1 C2 27.0(8) 2 . . . ? N1 Ni1 N1 C2 -51.7(9) 4 . . . ? N2 Ni1 N1 C4 0.000(1) . . . . ? N1 Ni1 N1 C4 -101.31(12) 3 . . . ? N1 Ni1 N1 C4 180.000(2) 2 . . . ? N1 Ni1 N1 C4 101.31(12) 4 . . . ? N2 Ni1 N1 C1 111.1(5) . . . 15_665 ? N1 Ni1 N1 C1 9.8(6) 3 . . 15_665 ? N1 Ni1 N1 C1 -68.9(5) 2 . . 15_665 ? N1 Ni1 N1 C1 -147.6(5) 4 . . 15_665 ? N2 Ni1 N1 C1 -111.1(5) . . . . ? N1 Ni1 N1 C1 147.6(5) 3 . . . ? N1 Ni1 N1 C1 68.9(5) 2 . . . ? N1 Ni1 N1 C1 -9.8(6) 4 . . . ? Ni1 N2 C5 C6 0(100) . . . . ? C2 N1 C2 C1 -171.6(10) 15_665 . . . ? C4 N1 C2 C1 -60.2(18) . . . . ? C1 N1 C2 C1 -166.2(17) 15_665 . . . ? Ni1 N1 C2 C1 89.0(14) . . . . ? C4 N1 C2 C2 111.4(9) . . . 15_665 ? C1 N1 C2 C2 5.4(7) 15_665 . . 15_665 ? C1 N1 C2 C2 171.6(10) . . . 15_665 ? Ni1 N1 C2 C2 -99.4(5) . . . 15_665 ? C2 N1 C2 C3 167.4(15) 15_665 . . . ? C4 N1 C2 C3 -81.2(19) . . . . ? C1 N1 C2 C3 172.9(18) 15_665 . . . ? C1 N1 C2 C3 -21.0(17) . . . . ? Ni1 N1 C2 C3 68.1(18) . . . . ? C2 N1 C2 C1 158.9(4) 15_665 . . 14_655 ? C4 N1 C2 C1 -89.7(10) . . . 14_655 ? C1 N1 C2 C1 164.3(9) 15_665 . . 14_655 ? C1 N1 C2 C1 -29.5(10) . . . 14_655 ? Ni1 N1 C2 C1 59.5(8) . . . 14_655 ? O4 Cl2 O3 O4 -151.6(9) . . . 12_656 ? O4 Cl2 O3 O4 151.6(9) 2_655 . . 12_656 ? O4 Cl2 O3 O4 0.000(5) 11_666 . . 12_656 ? O3 Cl2 O3 O4 -94.6(7) 11_666 . . 12_656 ? O3 Cl2 O3 O4 94.6(7) 12_656 . . 12_656 ? O3 Cl2 O3 O4 0.000(14) 2_655 . . 12_656 ? C2 C2 C1 C3 -164(2) 15_665 . . . ? N1 C2 C1 C3 -151.3(18) . . . . ? C1 C2 C1 C3 -41.0(19) 14_655 . . . ? C2 C2 C1 C1 -123.3(18) 15_665 . . 14_655 ? N1 C2 C1 C1 -110.3(9) . . . 14_655 ? C3 C2 C1 C1 41.0(19) . . . 14_655 ? C2 C2 C1 N1 -13.0(15) 15_665 . . . ? C3 C2 C1 N1 151.3(18) . . . . ? C1 C2 C1 N1 110.3(9) 14_655 . . . ? C2 C2 C1 C2 -123.3(18) 15_665 . . 14_655 ? N1 C2 C1 C2 -110.3(9) . . . 14_655 ? C3 C2 C1 C2 41.0(19) . . . 14_655 ? C1 C2 C1 C2 -0.002(5) 14_655 . . 14_655 ? C2 N1 C1 C3 55(3) 15_665 . . . ? C2 N1 C1 C3 49(3) . . . . ? C4 N1 C1 C3 -176(3) . . . . ? C1 N1 C1 C3 67(3) 15_665 . . . ? Ni1 N1 C1 C3 -54(3) . . . . ? C2 N1 C1 C2 6.5(8) 15_665 . . . ? C4 N1 C1 C2 135.2(15) . . . . ? C1 N1 C1 C2 18(2) 15_665 . . . ? Ni1 N1 C1 C2 -103.2(16) . . . . ? C2 N1 C1 C1 118.0(9) 15_665 . . 14_655 ? C2 N1 C1 C1 111.5(16) . . . 14_655 ? C4 N1 C1 C1 -113.3(4) . . . 14_655 ? C1 N1 C1 C1 129.8(7) 15_665 . . 14_655 ? Ni1 N1 C1 C1 8.3(5) . . . 14_655 ? C2 N1 C1 C2 91.8(14) 15_665 . . 14_655 ? C2 N1 C1 C2 85(2) . . . 14_655 ? C4 N1 C1 C2 -139.4(9) . . . 14_655 ? C1 N1 C1 C2 103.6(9) 15_665 . . 14_655 ? Ni1 N1 C1 C2 -17.9(10) . . . 14_655 ? O4 Cl2 O4 O4 131.4(2) 11_666 . . 2_655 ? O4 Cl2 O4 O4 -131.3(2) 12_656 . . 2_655 ? O3 Cl2 O4 O4 180.000(3) 11_666 . . 2_655 ? O3 Cl2 O4 O4 0.000(2) 12_656 . . 2_655 ? O3 Cl2 O4 O4 -92.2(3) . . . 2_655 ? O3 Cl2 O4 O4 92.2(3) 2_655 . . 2_655 ? O4 Cl2 O4 O3 180.000(2) 2_655 . . 11_666 ? O4 Cl2 O4 O3 -48.7(2) 11_666 . . 11_666 ? O4 Cl2 O4 O3 48.7(2) 12_656 . . 11_666 ? O3 Cl2 O4 O3 180.000(2) 12_656 . . 11_666 ? O3 Cl2 O4 O3 87.8(3) . . . 11_666 ? O3 Cl2 O4 O3 -87.8(3) 2_655 . . 11_666 ? C2 C1 C3 C1 133(2) . . . 14_655 ? N1 C1 C3 C1 93(3) . . . 14_655 ? C2 C1 C3 C1 35.0(12) 14_655 . . 14_655 ? C2 C1 C3 C2 98(3) . . . 14_655 ? C1 C1 C3 C2 -35.0(12) 14_655 . . 14_655 ? N1 C1 C3 C2 58(4) . . . 14_655 ? C1 C1 C3 C2 -133(2) 14_655 . . . ? N1 C1 C3 C2 -40.3(19) . . . . ? C2 C1 C3 C2 -98(3) 14_655 . . . ? C2 C2 C3 C1 126(6) 15_665 . . . ? N1 C2 C3 C1 32(2) . . . . ? C1 C2 C3 C1 52(3) 14_655 . . . ? C1 C2 C3 C1 -52(3) . . . 14_655 ? C2 C2 C3 C1 74(8) 15_665 . . 14_655 ? N1 C2 C3 C1 -20(4) . . . 14_655 ? C1 C2 C3 C2 -102(3) . . . 14_655 ? C2 C2 C3 C2 24(8) 15_665 . . 14_655 ? N1 C2 C3 C2 -70(3) . . . 14_655 ? C1 C2 C3 C2 -50(2) 14_655 . . 14_655 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.612 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.099 data_chem173 _database_code_depnum_ccdc_archive 'CCDC 900983' #TrackingRef 'Chem173.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H33 Cl N5 Ni O6' _chemical_formula_weight 473.62 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 7.7299(2) _cell_length_b 7.7263(2) _cell_length_c 17.8514(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.673(2) _cell_angle_gamma 90.00 _cell_volume 1047.70(5) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 2365 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 23.04 _exptl_crystal_description Block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 502 _exptl_absorpt_coefficient_mu 1.095 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8108 _exptl_absorpt_correction_T_max 0.8984 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8344 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_av_sigmaI/netI 0.0575 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3604 _reflns_number_gt 3188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.021(14) _refine_ls_number_reflns 3604 _refine_ls_number_parameters 258 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0801 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 Ni1 Ni 1.00111(4) 0.21251(5) 0.25593(3) 0.01812(12) Uani 1 1 d . . . Cl1 Cl 0.50379(12) 0.66138(13) 0.05367(6) 0.0311(2) Uani 1 1 d . . . O1 O 1.1067(3) -0.0069(3) 0.28024(15) 0.0270(6) Uani 1 1 d . . . O2 O 1.2293(4) 0.1248(4) 0.29506(16) 0.0280(7) Uani 1 1 d . . . O3 O 0.5334(6) 0.5571(7) 0.1200(3) 0.1054(19) Uani 1 1 d . . . O4 O 0.3976(6) 0.8031(5) 0.0677(3) 0.0614(12) Uani 1 1 d . . . O5 O 0.4143(6) 0.5630(8) -0.0058(3) 0.125(2) Uani 1 1 d . . . O6 O 0.6714(5) 0.7152(5) 0.0414(2) 0.0624(10) Uani 1 1 d . . . N4 N 1.0072(4) 0.1937(4) 0.13292(18) 0.0234(7) Uani 1 1 d . . . N1 N 0.7449(4) 0.1362(5) 0.22283(18) 0.0220(8) Uani 1 1 d . . . N2 N 0.9145(4) 0.2606(4) 0.36426(17) 0.0226(7) Uani 1 1 d . . . N3 N 1.0559(4) 0.4758(4) 0.26044(18) 0.0223(7) Uani 1 1 d . . . N5 N 0.6699(7) 0.2570(5) 0.9045(3) 0.0583(12) Uani 1 1 d . . . C12 C 0.8536(5) 0.0801(5) 0.1060(2) 0.0286(9) Uani 1 1 d . . . H12A H 0.8823 -0.0405 0.1225 0.034 Uiso 1 1 calc R . . H12B H 0.8245 0.0819 0.0496 0.034 Uiso 1 1 calc R . . C13 C 0.6978(5) 0.1431(5) 0.1386(2) 0.0293(9) Uani 1 1 d . . . H13A H 0.6679 0.2632 0.1217 0.035 Uiso 1 1 calc R . . H13B H 0.5941 0.0688 0.1205 0.035 Uiso 1 1 calc R . . C2 C 0.6413(5) 0.2520(5) 0.2623(2) 0.0278(9) Uani 1 1 d . . . H2A H 0.5172 0.2129 0.2535 0.033 Uiso 1 1 calc R . . H2B H 0.6442 0.3709 0.2418 0.033 Uiso 1 1 calc R . . C3 C 0.7165(5) 0.2522(5) 0.3476(2) 0.0319(10) Uani 1 1 d . . . H3A H 0.6688 0.3528 0.3715 0.038 Uiso 1 1 calc R . . H3B H 0.6779 0.1459 0.3708 0.038 Uiso 1 1 calc R . . C5 C 0.9763(6) 0.4355(5) 0.3874(2) 0.0306(10) Uani 1 1 d . . . H5A H 1.1007 0.4306 0.4137 0.037 Uiso 1 1 calc R . . H5B H 0.9056 0.4831 0.4235 0.037 Uiso 1 1 calc R . . C6 C 0.9602(6) 0.5529(6) 0.3183(2) 0.0258(10) Uani 1 1 d . . . H6A H 0.8344 0.5686 0.2954 0.031 Uiso 1 1 calc R . . H6B H 1.0104 0.6679 0.3342 0.031 Uiso 1 1 calc R . . C7 C 1.2474(5) 0.4999(6) 0.2881(2) 0.0339(10) Uani 1 1 d . . . H7A H 1.3129 0.4454 0.2523 0.051 Uiso 1 1 calc R . . H7B H 1.2813 0.4463 0.3384 0.051 Uiso 1 1 calc R . . H7C H 1.2746 0.6238 0.2918 0.051 Uiso 1 1 calc R . . C8 C 1.0044(6) 0.5775(5) 0.1885(2) 0.0292(10) Uani 1 1 d . . . H8A H 1.0432 0.6988 0.1983 0.035 Uiso 1 1 calc R . . H8B H 0.8744 0.5778 0.1740 0.035 Uiso 1 1 calc R . . C9 C 1.0809(6) 0.5087(6) 0.1223(2) 0.0332(10) Uani 1 1 d . . . H9A H 1.0777 0.6012 0.0837 0.040 Uiso 1 1 calc R . . H9B H 1.2057 0.4772 0.1407 0.040 Uiso 1 1 calc R . . C10 C 0.9844(6) 0.3541(5) 0.0856(2) 0.0301(9) Uani 1 1 d . . . H10A H 0.8574 0.3821 0.0730 0.036 Uiso 1 1 calc R . . H10B H 1.0248 0.3305 0.0371 0.036 Uiso 1 1 calc R . . C4 C 0.9856(6) 0.1386(6) 0.4261(2) 0.0334(10) Uani 1 1 d . . . H4A H 1.1145 0.1396 0.4342 0.050 Uiso 1 1 calc R . . H4B H 0.9424 0.0217 0.4118 0.050 Uiso 1 1 calc R . . H4C H 0.9469 0.1736 0.4731 0.050 Uiso 1 1 calc R . . C1 C 0.7184(6) -0.0471(5) 0.2467(3) 0.0369(10) Uani 1 1 d . . . H1A H 0.7647 -0.0599 0.3014 0.055 Uiso 1 1 calc R . . H1B H 0.7808 -0.1263 0.2180 0.055 Uiso 1 1 calc R . . H1C H 0.5925 -0.0746 0.2363 0.055 Uiso 1 1 calc R . . C11 C 1.1704(5) 0.1058(6) 0.1213(2) 0.0332(10) Uani 1 1 d . . . H11A H 1.1910 0.0036 0.1542 0.050 Uiso 1 1 calc R . . H11B H 1.2702 0.1855 0.1340 0.050 Uiso 1 1 calc R . . H11C H 1.1581 0.0702 0.0678 0.050 Uiso 1 1 calc R . . C14 C 0.5426(6) 0.2139(6) 0.9219(3) 0.0331(11) Uani 1 1 d . . . C15 C 0.3868(7) 0.1541(7) 0.9461(3) 0.0455(12) Uani 1 1 d . . . H15A H 0.4139 0.0495 0.9771 0.068 Uiso 1 1 calc R . . H15B H 0.2966 0.1275 0.9013 0.068 Uiso 1 1 calc R . . H15C H 0.3430 0.2442 0.9764 0.068 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 Ni1 0.0140(2) 0.0195(2) 0.0209(2) 0.0002(3) 0.00337(14) 0.0032(2) Cl1 0.0228(5) 0.0255(5) 0.0437(6) -0.0020(5) 0.0026(4) -0.0004(4) O1 0.0245(14) 0.0200(14) 0.0361(15) 0.0023(12) 0.0046(11) 0.0035(11) O2 0.0177(15) 0.0271(17) 0.0382(16) 0.0038(14) 0.0027(12) 0.0046(13) O3 0.055(3) 0.121(4) 0.146(4) 0.108(4) 0.033(3) 0.033(3) O4 0.057(3) 0.040(2) 0.087(3) -0.002(2) 0.012(2) 0.0199(18) O5 0.057(3) 0.150(5) 0.154(5) -0.122(4) -0.014(3) -0.009(3) O6 0.036(2) 0.087(3) 0.067(2) 0.006(2) 0.0158(18) -0.0147(19) N4 0.0226(18) 0.023(2) 0.0256(18) 0.0005(15) 0.0058(14) 0.0066(14) N1 0.0145(17) 0.0252(19) 0.0253(17) 0.0016(15) 0.0012(13) 0.0015(14) N2 0.0245(18) 0.0227(18) 0.0211(16) 0.0029(14) 0.0051(13) 0.0081(14) N3 0.0164(16) 0.0223(16) 0.0275(16) -0.0012(14) 0.0022(14) 0.0016(12) N5 0.062(3) 0.056(3) 0.064(3) -0.013(2) 0.028(2) -0.014(2) C12 0.030(2) 0.031(2) 0.0238(19) -0.0045(17) 0.0039(16) 0.0019(18) C13 0.023(2) 0.036(2) 0.027(2) -0.0031(18) 0.0008(16) -0.0050(18) C2 0.0182(19) 0.029(2) 0.036(2) -0.0049(17) 0.0065(16) 0.0023(16) C3 0.028(2) 0.037(3) 0.034(2) 0.0009(18) 0.0149(17) 0.0056(18) C5 0.037(2) 0.029(2) 0.025(2) -0.0036(19) 0.0044(18) 0.008(2) C6 0.025(2) 0.022(2) 0.030(2) -0.0077(18) 0.0015(17) 0.0056(18) C7 0.024(2) 0.029(2) 0.048(3) -0.003(2) 0.0040(18) -0.0019(18) C8 0.030(2) 0.022(2) 0.034(2) 0.000(2) 0.0035(18) -0.0010(19) C9 0.031(2) 0.035(3) 0.035(2) 0.009(2) 0.0091(18) -0.002(2) C10 0.036(2) 0.033(2) 0.023(2) 0.0082(18) 0.0083(17) 0.003(2) C4 0.041(3) 0.035(2) 0.026(2) 0.0052(19) 0.0087(18) 0.009(2) C1 0.035(2) 0.029(2) 0.046(3) 0.000(2) 0.0053(19) -0.0054(19) C11 0.028(2) 0.041(3) 0.034(2) -0.0024(19) 0.0145(18) 0.0098(19) C14 0.035(3) 0.031(2) 0.034(2) -0.006(2) 0.010(2) -0.002(2) C15 0.045(3) 0.052(3) 0.041(3) 0.008(2) 0.009(2) -0.017(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 Ni1 O1 1.897(3) . ? Ni1 O2 1.898(3) . ? Ni1 N1 2.046(3) . ? Ni1 N3 2.076(3) . ? Ni1 N2 2.192(3) . ? Ni1 N4 2.210(3) . ? Cl1 O5 1.382(4) . ? Cl1 O6 1.416(4) . ? Cl1 O3 1.416(4) . ? Cl1 O4 1.418(4) . ? O1 O2 1.383(4) . ? N4 C11 1.481(5) . ? N4 C12 1.483(5) . ? N4 C10 1.492(5) . ? N1 C2 1.466(5) . ? N1 C13 1.482(5) . ? N1 C1 1.504(5) . ? N2 C5 1.467(5) . ? N2 C4 1.478(5) . ? N2 C3 1.506(5) . ? N3 C7 1.483(5) . ? N3 C8 1.496(5) . ? N3 C6 1.501(5) . ? N5 C14 1.135(7) . ? C12 C13 1.512(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C2 C3 1.527(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C6 1.516(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.512(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.494(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C14 C15 1.430(7) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 O1 Ni1 O2 42.73(12) . . ? O1 Ni1 N1 99.26(13) . . ? O2 Ni1 N1 141.94(11) . . ? O1 Ni1 N3 142.25(12) . . ? O2 Ni1 N3 99.58(12) . . ? N1 Ni1 N3 118.25(13) . . ? O1 Ni1 N2 97.96(11) . . ? O2 Ni1 N2 98.67(12) . . ? N1 Ni1 N2 82.32(13) . . ? N3 Ni1 N2 83.86(12) . . ? O1 Ni1 N4 94.65(11) . . ? O2 Ni1 N4 98.79(12) . . ? N1 Ni1 N4 83.79(13) . . ? N3 Ni1 N4 93.51(12) . . ? N2 Ni1 N4 162.54(11) . . ? O5 Cl1 O6 112.6(3) . . ? O5 Cl1 O3 108.1(4) . . ? O6 Cl1 O3 106.6(2) . . ? O5 Cl1 O4 109.7(3) . . ? O6 Cl1 O4 112.1(3) . . ? O3 Cl1 O4 107.5(3) . . ? O2 O1 Ni1 68.69(16) . . ? O1 O2 Ni1 68.58(16) . . ? C11 N4 C12 109.6(3) . . ? C11 N4 C10 108.4(3) . . ? C12 N4 C10 107.7(3) . . ? C11 N4 Ni1 110.2(2) . . ? C12 N4 Ni1 101.4(2) . . ? C10 N4 Ni1 119.1(2) . . ? C2 N1 C13 114.3(3) . . ? C2 N1 C1 108.9(3) . . ? C13 N1 C1 107.5(3) . . ? C2 N1 Ni1 105.7(2) . . ? C13 N1 Ni1 109.0(2) . . ? C1 N1 Ni1 111.4(3) . . ? C5 N2 C4 108.8(3) . . ? C5 N2 C3 111.2(3) . . ? C4 N2 C3 110.1(3) . . ? C5 N2 Ni1 105.5(2) . . ? C4 N2 Ni1 114.7(2) . . ? C3 N2 Ni1 106.5(2) . . ? C7 N3 C8 108.1(3) . . ? C7 N3 C6 108.1(3) . . ? C8 N3 C6 107.2(3) . . ? C7 N3 Ni1 108.7(2) . . ? C8 N3 Ni1 117.5(2) . . ? C6 N3 Ni1 107.0(2) . . ? N4 C12 C13 109.4(3) . . ? N4 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? N4 C12 H12B 109.8 . . ? C13 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? N1 C13 C12 108.4(3) . . ? N1 C13 H13A 110.0 . . ? C12 C13 H13A 110.0 . . ? N1 C13 H13B 110.0 . . ? C12 C13 H13B 110.0 . . ? H13A C13 H13B 108.4 . . ? N1 C2 C3 109.8(3) . . ? N1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? N1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? N2 C3 C2 112.4(3) . . ? N2 C3 H3A 109.1 . . ? C2 C3 H3A 109.1 . . ? N2 C3 H3B 109.1 . . ? C2 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? N2 C5 C6 110.4(3) . . ? N2 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? N2 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? N3 C6 C5 110.2(3) . . ? N3 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N3 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N3 C7 H7A 109.5 . . ? N3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C9 113.9(3) . . ? N3 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? N3 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C10 C9 C8 112.9(3) . . ? C10 C9 H9A 109.0 . . ? C8 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? N4 C10 C9 114.7(3) . . ? N4 C10 H10A 108.6 . . ? C9 C10 H10A 108.6 . . ? N4 C10 H10B 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N5 C14 C15 177.4(6) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.362 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.061