# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Vadim Kukushkin' _publ_contact_author_email KUKUSHKIN@VK2100.SPB.EDU _publ_section_title ; Copper-mediated imine-nitrile coupling leading to unsymmetric 1,3,5-triazapentadienato complexes containing the incorporated iminoisoindolin-1-one moiety ; loop_ _publ_author_name 'Vadim Kukushkin' 'Matti Haukka' 'Maximilian N Kopylovich' 'Konstantin V Luzyanin' ; A.J.L.Pombeiro ; # Attachment 'all.cif' #TITLE #AUTHORS data_1 _database_code_depnum_ccdc_archive 'CCDC 682535' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 Cu N6 O2' _chemical_formula_sum 'C20 H16 Cu N6 O2' _chemical_formula_weight 435.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M '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 11.9682(14) _cell_length_b 3.8305(5) _cell_length_c 19.416(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.224(9) _cell_angle_gamma 90.00 _cell_volume 887.69(19) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2560 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 446 _exptl_absorpt_coefficient_mu 1.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6874 _exptl_absorpt_correction_T_max 0.9454 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _publ_section_exptl_refinement ; The Cu atom is located on a center of symmetry (inversion centre) and is coordinated by four N atoms in a slightly distorted square planar geometry. The NH hydrogen atom was located from the difference Fourier map and refined isotropically. Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-0.98 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 1.61 \%A from atom N3 and the deepest hole is located 0.82 \%A from atom Cu1. ; _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 7788 _diffrn_reflns_av_R_equivalents 0.0832 _diffrn_reflns_av_sigmaI/netI 0.0792 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1999 _reflns_number_gt 1352 _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.3.1e (Brandenburg, 2007)' _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^)+(0.0460P)^2^+0.7492P] 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 1999 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.0000 0.0000 0.0241(2) Uani 1 2 d S . . O1 O 0.19281(19) -0.2991(7) 0.12765(13) 0.0318(6) Uani 1 1 d . . . N1 N 0.0024(2) -0.2803(8) 0.08839(14) 0.0234(7) Uani 1 1 d . . . N2 N 0.1970(2) 0.3833(8) -0.09308(15) 0.0252(7) Uani 1 1 d . . . N3 N 0.1592(2) 0.0737(8) 0.00828(17) 0.0282(8) Uani 1 1 d . . . H3N H 0.191(3) -0.008(9) 0.0440(19) 0.019(9) Uiso 1 1 d . . . C1 C 0.0944(3) -0.3599(10) 0.13570(18) 0.0260(8) Uani 1 1 d . . . C2 C 0.0521(3) -0.5298(10) 0.19739(18) 0.0254(8) Uani 1 1 d . . . C3 C 0.1066(3) -0.6467(10) 0.25865(18) 0.0279(8) Uani 1 1 d . . . H3 H 0.1856 -0.6287 0.2670 0.033 Uiso 1 1 calc R . . C4 C 0.0410(3) -0.7905(10) 0.30694(19) 0.0309(9) Uani 1 1 d . . . H4 H 0.0758 -0.8707 0.3496 0.037 Uiso 1 1 calc R . . C5 C -0.0750(3) -0.8214(10) 0.29485(19) 0.0298(8) Uani 1 1 d . . . H5 H -0.1177 -0.9217 0.3291 0.036 Uiso 1 1 calc R . . C6 C -0.1287(3) -0.7058(10) 0.23272(18) 0.0273(8) Uani 1 1 d . . . H6 H -0.2074 -0.7299 0.2235 0.033 Uiso 1 1 calc R . . C7 C -0.0628(3) -0.5546(9) 0.18511(18) 0.0240(8) Uani 1 1 d . . . C8 C -0.0923(3) -0.3961(9) 0.11697(18) 0.0248(8) Uani 1 1 d . . . C9 C 0.3499(3) 0.2542(11) -0.0098(2) 0.0341(10) Uani 1 1 d . . . H9A H 0.3660 0.1511 0.0361 0.051 Uiso 1 1 calc R . . H9B H 0.3723 0.5003 -0.0087 0.051 Uiso 1 1 calc R . . H9C H 0.3918 0.1285 -0.0435 0.051 Uiso 1 1 calc R . . C10 C 0.2267(3) 0.2275(10) -0.02997(19) 0.0279(9) 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 0.0177(3) 0.0307(4) 0.0240(3) -0.0004(3) 0.0004(2) 0.0008(3) O1 0.0206(13) 0.0435(17) 0.0309(14) 0.0044(12) -0.0014(11) -0.0012(12) N1 0.0200(14) 0.0250(17) 0.0250(16) -0.0024(13) 0.0008(12) 0.0021(12) N2 0.0191(14) 0.0295(17) 0.0268(16) -0.0004(13) 0.0003(12) -0.0005(13) N3 0.0227(15) 0.037(2) 0.0244(16) 0.0019(14) -0.0050(13) 0.0001(14) C1 0.0224(18) 0.029(2) 0.0257(19) -0.0044(16) -0.0013(15) 0.0017(16) C2 0.0261(17) 0.0227(19) 0.0271(18) -0.0011(16) 0.0001(14) 0.0013(16) C3 0.0222(17) 0.031(2) 0.029(2) -0.0020(17) -0.0026(15) 0.0029(16) C4 0.036(2) 0.030(2) 0.026(2) -0.0009(17) -0.0020(16) 0.0023(17) C5 0.034(2) 0.029(2) 0.027(2) -0.0006(17) 0.0056(16) 0.0005(17) C6 0.0253(18) 0.029(2) 0.028(2) -0.0036(16) 0.0043(15) 0.0017(16) C7 0.0238(16) 0.023(2) 0.0252(18) -0.0006(15) 0.0004(14) 0.0010(15) C8 0.0253(18) 0.023(2) 0.0257(19) -0.0039(14) 0.0017(15) 0.0019(15) C9 0.0217(18) 0.040(2) 0.041(2) 0.0059(19) 0.0001(17) -0.0039(17) C10 0.0234(18) 0.031(2) 0.029(2) -0.0025(16) 0.0011(16) -0.0008(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 N3 1.921(3) 3 ? Cu1 N3 1.921(3) . yes Cu1 N1 2.023(3) 3 ? Cu1 N1 2.023(3) . yes O1 C1 1.222(4) . yes N1 C8 1.371(4) . ? N1 C1 1.414(4) . ? N2 C8 1.305(4) 3 yes N2 C10 1.386(5) . ? N3 C10 1.280(5) . ? N3 H3N 0.83(4) . ? C1 C2 1.484(5) . ? C2 C7 1.381(4) . ? C2 C3 1.388(5) . ? C3 C4 1.381(5) . ? C3 H3 0.9500 . ? C4 C5 1.396(5) . ? C4 H4 0.9500 . ? C5 C6 1.397(5) . ? C5 H5 0.9500 . ? C6 C7 1.386(5) . ? C6 H6 0.9500 . ? C7 C8 1.475(5) . ? C8 N2 1.305(4) 3 ? C9 C10 1.501(5) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 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 N3 Cu1 N3 180.0 3 . ? N3 Cu1 N1 93.15(12) 3 3 ? N3 Cu1 N1 86.85(12) . 3 ? N3 Cu1 N1 86.85(12) 3 . ? N3 Cu1 N1 93.15(12) . . yes N1 Cu1 N1 180.0 3 . ? C8 N1 C1 107.1(3) . . ? C8 N1 Cu1 123.7(2) . . ? C1 N1 Cu1 128.8(2) . . ? C8 N2 C10 120.5(3) 3 . yes C10 N3 Cu1 133.1(3) . . ? C10 N3 H3N 113(2) . . ? Cu1 N3 H3N 114(2) . . ? O1 C1 N1 126.0(3) . . ? O1 C1 C2 125.2(3) . . ? N1 C1 C2 108.9(3) . . ? C7 C2 C3 121.6(3) . . ? C7 C2 C1 106.6(3) . . ? C3 C2 C1 131.8(3) . . ? C4 C3 C2 117.1(3) . . ? C4 C3 H3 121.4 . . ? C2 C3 H3 121.4 . . ? C3 C4 C5 121.8(3) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C4 C5 C6 120.5(4) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 117.4(3) . . ? C7 C6 H6 121.3 . . ? C5 C6 H6 121.3 . . ? C2 C7 C6 121.5(3) . . ? C2 C7 C8 107.2(3) . . ? C6 C7 C8 131.3(3) . . ? N2 C8 N1 130.1(3) 3 . ? N2 C8 C7 119.6(3) 3 . ? N1 C8 C7 110.2(3) . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 N2 125.4(3) . . ? N3 C10 C9 122.0(3) . . ? N2 C10 C9 112.6(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N3 H3N O1 0.83(4) 1.97(4) 2.727(4) 152(3) . yes _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.396 _refine_diff_density_min -0.684 _refine_diff_density_rms 0.091 #===END======================================================================== data_2 _database_code_depnum_ccdc_archive 'CCDC 682536' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 Cu N6 O2, H2 O' _chemical_formula_sum 'C22 H22 Cu N6 O3' _chemical_formula_weight 482.00 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 '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 27.912(2) _cell_length_b 4.9750(2) _cell_length_c 17.4311(12) _cell_angle_alpha 90.00 _cell_angle_beta 124.989(2) _cell_angle_gamma 90.00 _cell_volume 1983.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6418 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 996 _exptl_absorpt_coefficient_mu 1.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8278 _exptl_absorpt_correction_T_max 0.9536 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _publ_section_exptl_refinement ; The Cu atom is located on a center of symmetry and is coordinated by four N atoms in a slightly distorted square planar geometry. The NH hydrogens were located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogens were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-0.99 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.78 \%A from atom H11A and the deepest hole is located 0.83 \%A from atom Cu1. ; _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 11792 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0422 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.43 _reflns_number_total 2186 _reflns_number_gt 1783 _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 'SIR97 (Altomare et al., 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^)+(0.0449P)^2^+6.7974P] 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 2186 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0435 _refine_ls_wR_factor_ref 0.1074 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.0000 0.5000 0.01696(16) Uani 1 2 d S . . O1 O -0.14551(8) -0.1157(4) 0.32574(14) 0.0270(5) Uani 1 1 d . . . O2 O 0.0000 0.9522(6) 0.2500 0.0333(7) Uani 1 2 d S . . H2O H 0.0041 0.8310 0.2994 0.050 Uiso 1 1 d R . . N1 N -0.06524(9) -0.2482(5) 0.47444(16) 0.0193(5) Uani 1 1 d . . . N2 N 0.01301(9) 0.5164(5) 0.38380(15) 0.0196(5) Uani 1 1 d . . . N3 N -0.04949(10) 0.1768(5) 0.38070(16) 0.0221(5) Uani 1 1 d . . . H3N H -0.0903 0.1106 0.3398 0.033 Uiso 1 1 d R . . C1 C -0.12345(11) -0.2546(6) 0.39648(19) 0.0204(6) Uani 1 1 d . . . C2 C -0.15597(12) -0.4631(6) 0.41083(19) 0.0205(6) Uani 1 1 d . . . C3 C -0.21432(12) -0.5338(6) 0.3562(2) 0.0237(6) Uani 1 1 d . . . H3 H -0.2415 -0.4475 0.2982 0.028 Uiso 1 1 calc R . . C4 C -0.23135(13) -0.7375(6) 0.3903(2) 0.0282(7) Uani 1 1 d . . . H4 H -0.2712 -0.7910 0.3553 0.034 Uiso 1 1 calc R . . C5 C -0.19095(12) -0.8649(6) 0.4752(2) 0.0255(6) Uani 1 1 d . . . H5 H -0.2039 -1.0047 0.4964 0.031 Uiso 1 1 calc R . . C6 C -0.13224(12) -0.7920(6) 0.5295(2) 0.0228(6) Uani 1 1 d . . . H6 H -0.1048 -0.8795 0.5870 0.027 Uiso 1 1 calc R . . C7 C -0.11553(11) -0.5859(6) 0.49586(18) 0.0196(6) Uani 1 1 d . . . C8 C -0.05899(11) -0.4473(5) 0.53467(19) 0.0187(6) Uani 1 1 d . . . C9 C -0.08380(13) 0.4596(6) 0.2416(2) 0.0291(7) Uani 1 1 d . . . H9A H -0.0924 0.6523 0.2425 0.035 Uiso 1 1 calc R . . H9B H -0.0663 0.4430 0.2059 0.035 Uiso 1 1 calc R . . C10 C -0.03865(13) 0.3703(6) 0.3417(2) 0.0265(6) Uani 1 1 d . . . C11 C -0.14054(13) 0.3077(7) 0.1904(2) 0.0346(7) Uani 1 1 d . . . H11A H -0.1592 0.3275 0.2236 0.052 Uiso 1 1 calc R . . H11B H -0.1330 0.1170 0.1872 0.052 Uiso 1 1 calc R . . H11C H -0.1665 0.3796 0.1268 0.052 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 0.0135(2) 0.0170(3) 0.0176(2) 0.00151(19) 0.00734(18) -0.00027(18) O1 0.0198(10) 0.0310(11) 0.0238(10) 0.0061(9) 0.0088(8) -0.0036(8) O2 0.0389(17) 0.0285(17) 0.0349(17) 0.000 0.0226(15) 0.000 N1 0.0163(10) 0.0185(11) 0.0204(11) -0.0006(9) 0.0091(9) -0.0013(9) N2 0.0155(10) 0.0210(12) 0.0204(11) 0.0032(10) 0.0092(9) -0.0009(9) N3 0.0203(11) 0.0220(12) 0.0203(11) 0.0006(10) 0.0096(10) 0.0014(9) C1 0.0165(12) 0.0202(14) 0.0236(14) -0.0005(11) 0.0111(11) -0.0013(10) C2 0.0178(12) 0.0222(14) 0.0212(13) -0.0018(11) 0.0109(11) -0.0013(11) C3 0.0177(12) 0.0270(15) 0.0208(13) -0.0013(12) 0.0076(11) -0.0035(11) C4 0.0204(13) 0.0297(16) 0.0299(15) -0.0026(13) 0.0117(12) -0.0067(12) C5 0.0264(15) 0.0241(15) 0.0281(15) -0.0019(12) 0.0168(13) -0.0082(12) C6 0.0237(14) 0.0215(14) 0.0231(14) -0.0001(11) 0.0134(12) -0.0013(11) C7 0.0178(13) 0.0213(13) 0.0188(13) -0.0033(11) 0.0100(11) -0.0023(10) C8 0.0171(12) 0.0205(14) 0.0213(13) -0.0019(11) 0.0126(11) -0.0003(10) C9 0.0291(15) 0.0289(17) 0.0278(15) 0.0064(13) 0.0155(13) 0.0065(12) C10 0.0230(14) 0.0256(16) 0.0294(15) -0.0017(13) 0.0140(13) 0.0026(12) C11 0.0288(16) 0.0359(18) 0.0262(16) -0.0001(14) 0.0081(13) 0.0105(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 N3 1.927(2) 5_556 ? Cu1 N3 1.927(2) . yes Cu1 N1 2.027(2) . yes Cu1 N1 2.027(2) 5_556 ? O1 C1 1.227(3) . yes O2 H2O 1.0025 . ? N1 C8 1.380(3) . yes N1 C1 1.398(3) . yes N2 C8 1.301(3) 5_556 yes N2 C10 1.390(4) . yes N3 C10 1.310(4) . yes N3 H3N 0.9910 . ? C1 C2 1.491(4) . ? C2 C3 1.380(4) . ? C2 C7 1.387(4) . ? C3 C4 1.390(4) . ? C3 H3 0.9500 . ? C4 C5 1.396(4) . ? C4 H4 0.9500 . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 C7 1.387(4) . ? C6 H6 0.9500 . ? C7 C8 1.483(4) . ? C8 N2 1.301(3) 5_556 ? C9 C11 1.502(4) . ? C9 C10 1.519(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 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 N3 Cu1 N3 179.997(1) 5_556 . ? N3 Cu1 N1 87.53(10) 5_556 . ? N3 Cu1 N1 92.47(10) . . yes N3 Cu1 N1 92.47(10) 5_556 5_556 ? N3 Cu1 N1 87.53(10) . 5_556 ? N1 Cu1 N1 180.00(9) . 5_556 ? C8 N1 C1 107.0(2) . . ? C8 N1 Cu1 124.36(18) . . ? C1 N1 Cu1 128.61(18) . . ? C8 N2 C10 120.9(2) 5_556 . yes C10 N3 Cu1 131.3(2) . . ? C10 N3 H3N 112.5 . . ? Cu1 N3 H3N 116.2 . . ? O1 C1 N1 126.7(2) . . ? O1 C1 C2 123.9(2) . . ? N1 C1 C2 109.4(2) . . ? C3 C2 C7 122.7(3) . . ? C3 C2 C1 130.7(3) . . ? C7 C2 C1 106.6(2) . . ? C2 C3 C4 116.6(3) . . ? C2 C3 H3 121.7 . . ? C4 C3 H3 121.7 . . ? C3 C4 C5 121.2(3) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C6 C5 C4 121.5(3) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C7 C6 C5 117.1(3) . . ? C7 C6 H6 121.4 . . ? C5 C6 H6 121.4 . . ? C6 C7 C2 120.8(3) . . ? C6 C7 C8 132.7(3) . . ? C2 C7 C8 106.5(2) . . ? N2 C8 N1 129.5(2) 5_556 . ? N2 C8 C7 120.0(2) 5_556 . ? N1 C8 C7 110.5(2) . . ? C11 C9 C10 115.7(3) . . ? C11 C9 H9A 108.4 . . ? C10 C9 H9A 108.4 . . ? C11 C9 H9B 108.4 . . ? C10 C9 H9B 108.4 . . ? H9A C9 H9B 107.4 . . ? N3 C10 N2 126.1(3) . . ? N3 C10 C9 121.6(3) . . ? N2 C10 C9 112.3(3) . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 _geom_hbond_publ_flag O2 H2O N2 1.00 2.06 3.050(3) 167.5 . yes N3 H3N O1 0.99 1.81 2.697(3) 147.4 . yes _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.919 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.111 #===END======================================================================== data_4 _database_code_depnum_ccdc_archive 'CCDC 682537' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Cu N6 O2' _chemical_formula_sum 'C24 H24 Cu N6 O2' _chemical_formula_weight 492.03 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/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 10.7199(7) _cell_length_b 5.2390(3) _cell_length_c 18.9373(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.191(3) _cell_angle_gamma 90.00 _cell_volume 1060.70(11) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 17298 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.541 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 510 _exptl_absorpt_coefficient_mu 1.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7893 _exptl_absorpt_correction_T_max 0.9516 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _publ_section_exptl_refinement ; The Cu atom is located on a center of symmetry (inversion centre) and is coordinated by four N atoms in a slightly distorted square planar geometry. The NH hydrogen atom was located from the difference Fourier map but constrained to ride on their parent atom, with U~iso~ = 1.5 U~eq~(parent atom). Other hydrogen atoms were positioned geometrically and were also constrained to ride on their parent atoms, with C---H = 0.95-1.00 \%A, and U~iso~ = 1.2-1.5 U~eq~(parent atom). The highest peak is located 0.70 \%A from atom C8 and the deepest hole is located 0.74 \%A from atom Cu1. ; _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 14215 _diffrn_reflns_av_R_equivalents 0.0791 _diffrn_reflns_av_sigmaI/netI 0.0522 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.53 _reflns_number_total 2434 _reflns_number_gt 1840 _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.3.1e (Brandenburg, 2007)' _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^)+(0.0488P)^2^+0.5932P] 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 2434 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.1014 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.5000 0.0000 1.0000 0.01933(15) Uani 1 2 d S . . O1 O 0.77428(16) -0.3357(3) 0.97949(9) 0.0261(4) Uani 1 1 d . . . N1 N 0.56123(18) -0.2946(4) 0.94316(10) 0.0200(4) Uani 1 1 d . . . N2 N 0.63284(19) 0.3942(4) 1.12705(10) 0.0220(5) Uani 1 1 d . . . N3 N 0.6619(2) 0.0514(4) 1.04876(11) 0.0240(5) Uani 1 1 d . . . H3N H 0.7262 -0.0586 1.0351 0.033(8) Uiso 1 1 d R . . C1 C 0.6813(2) -0.4035(5) 0.94312(12) 0.0219(5) Uani 1 1 d . . . C2 C 0.6780(2) -0.6168(5) 0.89063(12) 0.0215(5) Uani 1 1 d . . . C3 C 0.7711(2) -0.7808(5) 0.87151(12) 0.0245(5) Uani 1 1 d . . . H3 H 0.8543 -0.7695 0.8923 0.029 Uiso 1 1 calc R . . C4 C 0.7363(2) -0.9639(5) 0.82010(13) 0.0256(6) Uani 1 1 d . . . H4 H 0.7973 -1.0798 0.8052 0.031 Uiso 1 1 calc R . . C5 C 0.6135(2) -0.9793(5) 0.79031(13) 0.0242(5) Uani 1 1 d . . . H5 H 0.5924 -1.1061 0.7556 0.029 Uiso 1 1 calc R . . C6 C 0.5213(2) -0.8132(5) 0.81033(12) 0.0229(5) Uani 1 1 d . . . H6 H 0.4377 -0.8239 0.7902 0.027 Uiso 1 1 calc R . . C7 C 0.5571(2) -0.6307(5) 0.86107(12) 0.0205(5) Uani 1 1 d . . . C8 C 0.4850(2) -0.4249(5) 0.89410(12) 0.0206(5) Uani 1 1 d . . . C9 C 0.8364(2) 0.1890(5) 1.13094(13) 0.0230(5) Uani 1 1 d . . . H9 H 0.8519 0.3391 1.1630 0.028 Uiso 1 1 calc R . . C10 C 0.7027(2) 0.2066(5) 1.09843(12) 0.0217(5) Uani 1 1 d . . . C11 C 0.8521(3) -0.0520(6) 1.17561(16) 0.0400(8) Uani 1 1 d . . . H11A H 0.7943 -0.0471 1.2134 0.060 Uiso 1 1 calc R . . H11B H 0.9383 -0.0623 1.1966 0.060 Uiso 1 1 calc R . . H11C H 0.8338 -0.2018 1.1456 0.060 Uiso 1 1 calc R . . C12 C 0.9322(3) 0.1968(7) 1.07519(15) 0.0421(8) Uani 1 1 d . . . H12A H 0.9274 0.0382 1.0477 0.063 Uiso 1 1 calc R . . H12B H 1.0164 0.2149 1.0986 0.063 Uiso 1 1 calc R . . H12C H 0.9144 0.3422 1.0435 0.063 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 0.0196(2) 0.0208(2) 0.0176(2) -0.00163(18) 0.00113(15) 0.00110(18) O1 0.0224(9) 0.0278(10) 0.0277(9) -0.0049(8) -0.0005(7) 0.0017(8) N1 0.0198(10) 0.0214(11) 0.0189(9) 0.0004(8) 0.0028(8) 0.0006(8) N2 0.0233(11) 0.0219(11) 0.0209(10) -0.0015(9) 0.0027(8) 0.0011(9) N3 0.0228(11) 0.0269(12) 0.0224(10) -0.0049(9) 0.0021(8) 0.0045(9) C1 0.0255(13) 0.0212(12) 0.0192(12) 0.0022(10) 0.0039(10) 0.0015(11) C2 0.0265(13) 0.0211(12) 0.0173(11) 0.0025(10) 0.0039(10) 0.0002(11) C3 0.0255(13) 0.0249(13) 0.0233(12) 0.0029(11) 0.0033(10) 0.0028(11) C4 0.0288(14) 0.0255(14) 0.0237(12) 0.0008(10) 0.0095(10) 0.0036(11) C5 0.0315(14) 0.0219(13) 0.0195(11) -0.0020(11) 0.0048(10) -0.0016(11) C6 0.0250(13) 0.0238(13) 0.0199(11) 0.0001(10) 0.0022(10) -0.0015(11) C7 0.0231(13) 0.0197(13) 0.0190(12) 0.0033(10) 0.0045(10) 0.0039(10) C8 0.0230(13) 0.0224(12) 0.0170(11) 0.0033(9) 0.0049(10) -0.0010(10) C9 0.0228(13) 0.0229(13) 0.0229(12) -0.0024(10) -0.0011(10) -0.0006(10) C10 0.0227(13) 0.0224(13) 0.0203(11) 0.0040(10) 0.0031(9) -0.0010(10) C11 0.0371(17) 0.0393(18) 0.0409(16) 0.0088(13) -0.0152(13) -0.0039(13) C12 0.0224(14) 0.065(2) 0.0388(16) 0.0075(16) 0.0020(12) 0.0044(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 N3 1.924(2) 3_657 ? Cu1 N3 1.924(2) . yes Cu1 N1 2.019(2) 3_657 ? Cu1 N1 2.019(2) . yes O1 C1 1.222(3) . yes N1 C8 1.373(3) . ? N1 C1 1.408(3) . ? N2 C8 1.307(3) 3_657 yes N2 C10 1.371(3) . ? N3 C10 1.295(3) . ? N3 H3N 0.9481 . ? C1 C2 1.494(4) . ? C2 C7 1.376(3) . ? C2 C3 1.385(3) . ? C3 C4 1.398(4) . ? C3 H3 0.9500 . ? C4 C5 1.397(4) . ? C4 H4 0.9500 . ? C5 C6 1.390(3) . ? C5 H5 0.9500 . ? C6 C7 1.389(3) . ? C6 H6 0.9500 . ? C7 C8 1.490(3) . ? C8 N2 1.307(3) 3_657 ? C9 C10 1.521(3) . ? C9 C11 1.522(4) . ? C9 C12 1.526(4) . ? C9 H9 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 N3 Cu1 N3 179.998(1) 3_657 . ? N3 Cu1 N1 92.62(8) 3_657 3_657 ? N3 Cu1 N1 87.38(8) . 3_657 ? N3 Cu1 N1 87.38(8) 3_657 . ? N3 Cu1 N1 92.62(8) . . yes N1 Cu1 N1 179.999(1) 3_657 . ? C8 N1 C1 107.3(2) . . ? C8 N1 Cu1 122.71(16) . . ? C1 N1 Cu1 130.02(16) . . ? C8 N2 C10 120.7(2) 3_657 . yes C10 N3 Cu1 132.91(18) . . ? C10 N3 H3N 111.5 . . ? Cu1 N3 H3N 115.6 . . ? O1 C1 N1 126.2(2) . . ? O1 C1 C2 124.8(2) . . ? N1 C1 C2 109.1(2) . . ? C7 C2 C3 122.4(2) . . ? C7 C2 C1 106.6(2) . . ? C3 C2 C1 131.0(2) . . ? C2 C3 C4 116.6(2) . . ? C2 C3 H3 121.7 . . ? C4 C3 H3 121.7 . . ? C5 C4 C3 121.1(2) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 121.4(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C7 C6 C5 117.0(2) . . ? C7 C6 H6 121.5 . . ? C5 C6 H6 121.5 . . ? C2 C7 C6 121.5(2) . . ? C2 C7 C8 107.0(2) . . ? C6 C7 C8 131.5(2) . . ? N2 C8 N1 131.3(2) 3_657 . ? N2 C8 C7 118.6(2) 3_657 . ? N1 C8 C7 110.0(2) . . ? C10 C9 C11 109.7(2) . . ? C10 C9 C12 112.4(2) . . ? C11 C9 C12 110.7(2) . . ? C10 C9 H9 108.0 . . ? C11 C9 H9 108.0 . . ? C12 C9 H9 108.0 . . ? N3 C10 N2 124.9(2) . . ? N3 C10 C9 120.9(2) . . ? N2 C10 C9 114.1(2) . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 _geom_hbond_publ_flag N3 H3N O1 0.95 1.89 2.741(3) 148.5 . yes _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.334 _refine_diff_density_min -0.537 _refine_diff_density_rms 0.078