# Electronic Supplementary Material (ESI) for CrystEngComm # 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_compound1 _database_code_depnum_ccdc_archive 'CCDC 917087' #TrackingRef 'web_deposit_cif_file_0_Jian-ZhenLiao_1356326008.compound1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Cd N10 O2' _chemical_formula_weight 364.62 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Fdd2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' _cell_length_a 15.916(3) _cell_length_b 19.127(4) _cell_length_c 8.2011(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2496.7(9) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2280 _cell_measurement_theta_min 3.3312 _cell_measurement_theta_max 27.4584 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.940 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1424 _exptl_absorpt_coefficient_mu 1.767 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.9223 _exptl_absorpt_correction_T_max 0.9617 _exptl_absorpt_process_details 'RAPID AUTO (Rigaku Corporation, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5047 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1293 _reflns_number_gt 1281 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007) (Rigaku, 2002)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-V (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0233P)^2^+3.5991P] 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 0.03(4) _refine_ls_number_reflns 1293 _refine_ls_number_parameters 87 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0199 _refine_ls_R_factor_gt 0.0196 _refine_ls_wR_factor_ref 0.0481 _refine_ls_wR_factor_gt 0.0476 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.153 _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 Cd1 Cd 0.2500 0.7500 1.92870(9) 0.02685(8) Uani 1 2 d S . . N2 N 0.06545(16) 0.81776(11) 1.9163(4) 0.0367(6) Uani 1 1 d . . . C1 C 0.14802(17) 0.89044(13) 2.0290(4) 0.0275(6) Uani 1 1 d . . . N1 N 0.14494(15) 0.82582(11) 1.9701(3) 0.0309(6) Uani 1 1 d . . . N4 N 0.07411(17) 0.92247(13) 2.0134(4) 0.0336(6) Uani 1 1 d . . . N3 N 0.02318(19) 0.87456(14) 1.9404(5) 0.0396(6) Uani 1 1 d . . . O1 O 0.30289(17) 0.82962(12) 2.1308(3) 0.0478(7) Uani 1 1 d . . . N5 N 0.21714(16) 0.92323(12) 2.0945(4) 0.0357(6) Uani 1 1 d . . . H5 H 0.2142 0.9679 2.1053 0.043 Uiso 1 1 calc R . . C2 C 0.2895(2) 0.89222(16) 2.1438(4) 0.0364(7) Uani 1 1 d . . . C3 C 0.3543(2) 0.94206(19) 2.2100(6) 0.0584(12) Uani 1 1 d . . . H3A H 0.3324 0.9888 2.2076 0.088 Uiso 1 1 calc R . . H3B H 0.4042 0.9396 2.1444 0.088 Uiso 1 1 calc R . . H3C H 0.3677 0.9295 2.3204 0.088 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 Cd1 0.02175(13) 0.01227(11) 0.04652(15) 0.000 0.000 0.00191(9) N2 0.0263(12) 0.0217(10) 0.0621(18) -0.0109(13) -0.0062(13) 0.0015(9) C1 0.0264(14) 0.0171(12) 0.0390(15) -0.0060(10) -0.0030(12) 0.0028(10) N1 0.0249(13) 0.0170(10) 0.0508(16) -0.0083(9) -0.0012(10) 0.0035(8) N4 0.0269(12) 0.0209(11) 0.0530(16) -0.0128(11) -0.0059(11) 0.0048(9) N3 0.0281(11) 0.0269(12) 0.0637(18) -0.0151(13) -0.0095(13) 0.0048(11) O1 0.0471(14) 0.0308(11) 0.0654(17) -0.0130(11) -0.0231(12) 0.0154(10) N5 0.0262(13) 0.0192(11) 0.0617(18) -0.0131(11) -0.0078(13) 0.0047(10) C2 0.0286(17) 0.0349(15) 0.0458(19) -0.0097(13) -0.0095(13) 0.0073(12) C3 0.042(2) 0.0441(19) 0.089(3) -0.023(2) -0.028(2) 0.0048(15) _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 Cd1 N1 2.239(2) 14_565 ? Cd1 N1 2.239(2) . ? Cd1 N4 2.330(3) 7_544 ? Cd1 N4 2.330(3) 8_564 ? Cd1 O1 2.403(2) . ? Cd1 O1 2.403(2) 14_565 ? N2 N3 1.293(3) . ? N2 N1 1.349(4) . ? C1 N1 1.328(3) . ? C1 N4 1.332(4) . ? C1 N5 1.376(4) . ? N4 N3 1.362(4) . ? N4 Cd1 2.330(3) 3 ? O1 C2 1.221(4) . ? N5 C2 1.356(4) . ? C2 C3 1.506(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 N1 Cd1 N1 162.57(15) 14_565 . ? N1 Cd1 N4 93.10(9) 14_565 7_544 ? N1 Cd1 N4 97.02(9) . 7_544 ? N1 Cd1 N4 97.02(9) 14_565 8_564 ? N1 Cd1 N4 93.10(9) . 8_564 ? N4 Cd1 N4 108.83(14) 7_544 8_564 ? N1 Cd1 O1 92.54(9) 14_565 . ? N1 Cd1 O1 75.33(8) . . ? N4 Cd1 O1 169.12(10) 7_544 . ? N4 Cd1 O1 79.67(10) 8_564 . ? N1 Cd1 O1 75.33(8) 14_565 14_565 ? N1 Cd1 O1 92.54(9) . 14_565 ? N4 Cd1 O1 79.67(10) 7_544 14_565 ? N4 Cd1 O1 169.12(10) 8_564 14_565 ? O1 Cd1 O1 92.78(14) . 14_565 ? N3 N2 N1 110.0(2) . . ? N1 C1 N4 111.1(3) . . ? N1 C1 N5 126.6(3) . . ? N4 C1 N5 122.3(2) . . ? C1 N1 N2 105.1(2) . . ? C1 N1 Cd1 129.1(2) . . ? N2 N1 Cd1 125.24(17) . . ? C1 N4 N3 105.0(2) . . ? C1 N4 Cd1 133.1(2) . 3 ? N3 N4 Cd1 112.5(2) . 3 ? N2 N3 N4 108.8(3) . . ? C2 O1 Cd1 128.3(2) . . ? C2 N5 C1 126.6(3) . . ? O1 C2 N5 123.5(3) . . ? O1 C2 C3 122.1(3) . . ? N5 C2 C3 114.4(3) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.221 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.077 data_compound2 _database_code_depnum_ccdc_archive 'CCDC 917088' #TrackingRef 'compound2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 N10 O2 Zn' _chemical_formula_sum 'C6 H8 N10 O3 Zn' _chemical_formula_weight 333.59 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 17.665(3) _cell_length_b 10.105(2) _cell_length_c 7.1333(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.73(3) _cell_angle_gamma 90.00 _cell_volume 1272.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2300 _cell_measurement_theta_min 3.6185 _cell_measurement_theta_max 27.4855 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.741 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 1.957 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.8201 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'RAPID AUTO (Rigaku Corporation, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5160 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1426 _reflns_number_gt 1391 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007) (Rigaku, 2002)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-V (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0307P)^2^+2.6231P] 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_number_reflns 1426 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _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 Zn1 Zn 0.0000 0.40526(4) 0.2500 0.02114(14) Uani 1 2 d S . . O1 O 0.06872(10) 0.24845(19) 0.3801(3) 0.0353(4) Uani 1 1 d . . . N1 N 0.07369(10) 0.37984(18) 0.0323(3) 0.0207(4) Uani 1 1 d . . . N2 N 0.07632(10) 0.4508(2) -0.1280(3) 0.0243(4) Uani 1 1 d . . . N3 N 0.14075(12) 0.4303(3) -0.2085(3) 0.0372(5) Uani 1 1 d . . . N4 N 0.18242(12) 0.3454(3) -0.1032(3) 0.0362(5) Uani 1 1 d . . . N5 N 0.16636(11) 0.2334(2) 0.1829(3) 0.0309(5) Uani 1 1 d . . . H5 H 0.2093 0.1958 0.1669 0.037 Uiso 1 1 d R . . C1 C 0.13993(13) 0.3177(2) 0.0420(3) 0.0239(5) Uani 1 1 d . . . C2 C 0.13113(14) 0.2031(3) 0.3413(4) 0.0308(5) Uani 1 1 d . . . C3 C 0.17216(19) 0.1078(3) 0.4694(5) 0.0518(9) Uani 1 1 d . . . H3A H 0.2194 0.0835 0.4162 0.078 Uiso 1 1 calc R . . H3B H 0.1417 0.0301 0.4849 0.078 Uiso 1 1 calc R . . H3C H 0.1816 0.1488 0.5893 0.078 Uiso 1 1 calc R . . OW1 O 0.5000 0.3797(11) 0.2500 0.113(4) Uani 0.50 2 d SP A 1 OW2 O 0.4791(6) 0.4429(11) 0.068(2) 0.083(4) Uani 0.25 1 d P . 2 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 Zn1 0.0145(2) 0.0271(2) 0.0221(2) 0.000 0.00419(13) 0.000 O1 0.0278(9) 0.0416(10) 0.0370(10) 0.0129(8) 0.0117(8) 0.0121(8) N1 0.0152(9) 0.0253(9) 0.0217(9) 0.0004(7) 0.0018(7) 0.0023(7) N2 0.0165(9) 0.0333(10) 0.0232(9) 0.0034(8) 0.0040(7) 0.0053(8) N3 0.0236(11) 0.0558(14) 0.0326(11) 0.0136(10) 0.0098(9) 0.0161(10) N4 0.0240(11) 0.0529(14) 0.0322(11) 0.0143(10) 0.0093(9) 0.0171(10) N5 0.0215(10) 0.0406(12) 0.0309(10) 0.0095(9) 0.0062(8) 0.0147(9) C1 0.0186(10) 0.0295(11) 0.0238(10) 0.0008(9) 0.0031(9) 0.0044(9) C2 0.0273(12) 0.0338(12) 0.0313(12) 0.0055(10) 0.0040(10) 0.0082(10) C3 0.0465(18) 0.066(2) 0.0438(17) 0.0256(15) 0.0095(14) 0.0246(16) OW1 0.147(11) 0.087(7) 0.108(9) 0.000 0.057(8) 0.000 OW2 0.058(7) 0.065(7) 0.126(11) -0.044(7) 0.004(7) 0.031(6) _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 Zn1 N1 2.0720(19) . ? Zn1 N1 2.0720(19) 2 ? Zn1 N2 2.1492(19) 6_566 ? Zn1 N2 2.1492(19) 5_565 ? Zn1 O1 2.1858(18) 2 ? Zn1 O1 2.1858(18) . ? O1 C2 1.233(3) . ? N1 C1 1.328(3) . ? N1 N2 1.352(3) . ? N2 N3 1.307(3) . ? N2 Zn1 2.1492(19) 5_565 ? N3 N4 1.345(3) . ? N4 C1 1.327(3) . ? N5 C2 1.342(3) . ? N5 C1 1.388(3) . ? N5 H5 0.8584 . ? C2 C3 1.500(4) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? OW2 OW2 1.69(3) 5_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N1 165.76(11) . 2 ? N1 Zn1 N2 89.24(7) . 6_566 ? N1 Zn1 N2 100.43(7) 2 6_566 ? N1 Zn1 N2 100.43(7) . 5_565 ? N1 Zn1 N2 89.24(7) 2 5_565 ? N2 Zn1 N2 94.83(11) 6_566 5_565 ? N1 Zn1 O1 86.87(7) . 2 ? N1 Zn1 O1 82.81(7) 2 2 ? N2 Zn1 O1 174.89(7) 6_566 2 ? N2 Zn1 O1 89.14(8) 5_565 2 ? N1 Zn1 O1 82.81(7) . . ? N1 Zn1 O1 86.87(7) 2 . ? N2 Zn1 O1 89.14(8) 6_566 . ? N2 Zn1 O1 174.89(7) 5_565 . ? O1 Zn1 O1 87.08(11) 2 . ? C2 O1 Zn1 131.52(17) . . ? C1 N1 N2 103.99(18) . . ? C1 N1 Zn1 126.33(15) . . ? N2 N1 Zn1 127.34(14) . . ? N3 N2 N1 109.88(18) . . ? N3 N2 Zn1 118.27(15) . 5_565 ? N1 N2 Zn1 131.64(14) . 5_565 ? N2 N3 N4 109.0(2) . . ? C1 N4 N3 104.93(19) . . ? C2 N5 C1 126.6(2) . . ? C2 N5 H5 116.4 . . ? C1 N5 H5 117.0 . . ? N4 C1 N1 112.2(2) . . ? N4 C1 N5 120.6(2) . . ? N1 C1 N5 127.2(2) . . ? O1 C2 N5 123.0(2) . . ? O1 C2 C3 121.4(2) . . ? N5 C2 C3 115.6(2) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? 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 Zn1 O1 C2 15.0(2) . . . . ? N1 Zn1 O1 C2 -174.9(2) 2 . . . ? N2 Zn1 O1 C2 -74.4(2) 6_566 . . . ? N2 Zn1 O1 C2 144.6(7) 5_565 . . . ? O1 Zn1 O1 C2 102.2(3) 2 . . . ? N1 Zn1 N1 C1 -60.04(18) 2 . . . ? N2 Zn1 N1 C1 73.1(2) 6_566 . . . ? N2 Zn1 N1 C1 167.87(19) 5_565 . . . ? O1 Zn1 N1 C1 -103.6(2) 2 . . . ? O1 Zn1 N1 C1 -16.14(19) . . . . ? N1 Zn1 N1 N2 140.16(18) 2 . . . ? N2 Zn1 N1 N2 -86.71(15) 6_566 . . . ? N2 Zn1 N1 N2 8.1(2) 5_565 . . . ? O1 Zn1 N1 N2 96.61(18) 2 . . . ? O1 Zn1 N1 N2 -175.94(19) . . . . ? C1 N1 N2 N3 0.4(3) . . . . ? Zn1 N1 N2 N3 163.79(17) . . . . ? C1 N1 N2 Zn1 -173.98(16) . . . 5_565 ? Zn1 N1 N2 Zn1 -10.6(3) . . . 5_565 ? N1 N2 N3 N4 -0.2(3) . . . . ? Zn1 N2 N3 N4 175.11(18) 5_565 . . . ? N2 N3 N4 C1 -0.2(3) . . . . ? N3 N4 C1 N1 0.5(3) . . . . ? N3 N4 C1 N5 -178.9(2) . . . . ? N2 N1 C1 N4 -0.6(3) . . . . ? Zn1 N1 C1 N4 -164.15(18) . . . . ? N2 N1 C1 N5 178.7(2) . . . . ? Zn1 N1 C1 N5 15.2(4) . . . . ? C2 N5 C1 N4 176.1(3) . . . . ? C2 N5 C1 N1 -3.2(4) . . . . ? Zn1 O1 C2 N5 -9.9(4) . . . . ? Zn1 O1 C2 C3 171.0(2) . . . . ? C1 N5 C2 O1 0.2(4) . . . . ? C1 N5 C2 C3 179.4(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 N5 H5 N4 0.86 2.02 2.861(3) 164.9 7 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.341 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.071 #end data_compound3 _database_code_depnum_ccdc_archive 'CCDC 917089' #TrackingRef 'web_deposit_cif_file_4_Jian-ZhenLiao_1356326008.compound3.cif' _audit_update_record ; 2012-06-25 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Cu N10 O2' _chemical_formula_weight 315.76 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 P21/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 7.0989(14) _cell_length_b 9.0946(18) _cell_length_c 8.1688(16) _cell_angle_alpha 90.00 _cell_angle_beta 102.65(3) _cell_angle_gamma 90.00 _cell_volume 514.59(18) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1737 _cell_measurement_theta_min 3.3982 _cell_measurement_theta_max 27.4816 _exptl_crystal_description Block _exptl_crystal_colour Blue _exptl_crystal_size_max 0.2500 _exptl_crystal_size_mid 0.1200 _exptl_crystal_size_min 0.1100 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.038 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 2.143 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7806 _exptl_absorpt_correction_T_max 0.8700 _exptl_absorpt_process_details 'RAPID AUTO (Rigaku Corporation, 1998)' _exptl_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4149 _diffrn_reflns_av_R_equivalents 0.0412 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1172 _reflns_number_gt 1126 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-V (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0292P)^2^+0.7168P] 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_number_reflns 1172 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0851 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _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 1.0000 0.5000 0.02229(16) Uani 1 2 d S . . O1 O 0.1722(3) 1.0397(2) 0.3433(2) 0.0231(4) Uani 1 1 d . . . N1 N 0.3804(3) 0.8469(2) 0.4004(3) 0.0224(5) Uani 1 1 d . . . H1 H 0.4682 0.7981 0.3663 0.027 Uiso 1 1 calc R . . N4 N 0.3506(3) 0.6960(2) 0.7809(3) 0.0241(5) Uani 1 1 d . . . N5 N 0.4434(3) 0.7085(2) 0.6533(3) 0.0245(5) Uani 1 1 d . . . N2 N 0.1882(3) 0.8546(2) 0.6102(3) 0.0196(4) Uani 1 1 d . . . N3 N 0.1999(3) 0.7822(2) 0.7568(3) 0.0228(5) Uani 1 1 d . . . C1 C 0.3511(4) 0.9761(3) 0.1390(4) 0.0279(6) Uani 1 1 d . . . H1A H 0.4454 0.9031 0.1285 0.042 Uiso 1 1 calc R . . H1B H 0.4053 1.0723 0.1344 0.042 Uiso 1 1 calc R . . H1C H 0.2397 0.9653 0.0490 0.042 Uiso 1 1 calc R . . C2 C 0.2934(4) 0.9569(3) 0.3028(3) 0.0202(5) Uani 1 1 d . . . C3 C 0.3389(3) 0.8062(3) 0.5525(3) 0.0189(5) 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 0.0211(3) 0.0259(3) 0.0227(2) 0.00750(17) 0.01082(18) 0.00721(17) O1 0.0240(9) 0.0233(9) 0.0251(9) 0.0033(7) 0.0121(8) 0.0038(7) N1 0.0234(11) 0.0264(11) 0.0197(10) 0.0027(8) 0.0101(9) 0.0062(9) N4 0.0242(11) 0.0262(12) 0.0217(10) 0.0039(9) 0.0049(9) 0.0009(9) N5 0.0243(11) 0.0279(12) 0.0214(11) 0.0045(9) 0.0055(9) 0.0043(9) N2 0.0200(10) 0.0223(10) 0.0178(9) 0.0014(8) 0.0067(8) 0.0014(8) N3 0.0238(11) 0.0249(11) 0.0210(10) 0.0044(8) 0.0078(9) 0.0009(9) C1 0.0304(15) 0.0338(15) 0.0226(12) 0.0050(11) 0.0129(11) 0.0052(11) C2 0.0200(12) 0.0221(12) 0.0193(11) 0.0005(9) 0.0058(10) -0.0033(10) C3 0.0184(11) 0.0202(12) 0.0178(11) -0.0007(9) 0.0033(9) -0.0001(9) _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 N2 1.954(2) . ? Cu1 N2 1.954(2) 3_576 ? Cu1 O1 1.9873(19) 3_576 ? Cu1 O1 1.9873(19) . ? O1 C2 1.242(3) . ? N1 C2 1.343(3) . ? N1 C3 1.388(3) . ? N4 N3 1.306(3) . ? N4 N5 1.355(3) . ? N5 C3 1.323(3) . ? N2 C3 1.334(3) . ? N2 N3 1.353(3) . ? C1 C2 1.492(4) . ? 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 Cu1 N2 180.000(1) . 3_576 ? N2 Cu1 O1 92.01(8) . 3_576 ? N2 Cu1 O1 87.99(8) 3_576 3_576 ? N2 Cu1 O1 87.99(8) . . ? N2 Cu1 O1 92.01(8) 3_576 . ? O1 Cu1 O1 180.0 3_576 . ? C2 O1 Cu1 128.39(17) . . ? C2 N1 C3 124.7(2) . . ? N3 N4 N5 110.8(2) . . ? C3 N5 N4 103.5(2) . . ? C3 N2 N3 104.7(2) . . ? C3 N2 Cu1 125.51(17) . . ? N3 N2 Cu1 129.79(17) . . ? N4 N3 N2 108.3(2) . . ? O1 C2 N1 123.3(2) . . ? O1 C2 C1 120.6(2) . . ? N1 C2 C1 116.0(2) . . ? N5 C3 N2 112.7(2) . . ? N5 C3 N1 122.4(2) . . ? N2 C3 N1 124.9(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N3 0.86 2.16 3.010(3) 168.2 4_675 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.469 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.079 data_compound4 _database_code_depnum_ccdc_archive 'CCDC 917090' #TrackingRef 'web_deposit_cif_file_6_Jian-ZhenLiao_1356326008.compound4.cif' _audit_update_record ; 2012-06-25 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 Mn N10 O2' _chemical_formula_weight 307.16 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y, z+1/2' 'x+1/2, -y, z+1/2' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1' 'x+1/2, -y+1/2, z+1' _cell_length_a 9.3707(19) _cell_length_b 12.181(2) _cell_length_c 9.1857(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1048.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 1580 _cell_measurement_theta_min 3.3450 _cell_measurement_theta_max 27.4932 _exptl_crystal_description Block _exptl_crystal_colour White _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.946 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 1.280 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9331 _exptl_absorpt_correction_T_max 0.9607 _exptl_absorpt_process_details 'RAPID AUTO (Rigaku Corporation, 1998)' _exptl_special_details ? _diffrn_ambient_temperature 113(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 'Rigaku Mercury CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4135 _diffrn_reflns_av_R_equivalents 0.0565 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1160 _reflns_number_gt 1115 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-V (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+11.9992P] 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 0.0(4) _refine_ls_number_reflns 1160 _refine_ls_number_parameters 70 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0705 _refine_ls_wR_factor_ref 0.1888 _refine_ls_wR_factor_gt 0.1862 _refine_ls_goodness_of_fit_ref 1.303 _refine_ls_restrained_S_all 1.302 _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 Mn1 Mn 0.0000 0.0000 0.6262(4) 0.0137(4) Uani 1 2 d S . . N3 N 0.1690(8) -0.0392(6) 0.7944(8) 0.0164(14) Uani 1 1 d . . . N4 N 0.2456(12) 0.0214(4) 0.8690(12) 0.0159(9) Uani 1 1 d . . . N2 N 0.1956(8) -0.1511(6) 0.8255(7) 0.0170(14) Uani 1 1 d . . . N1 N 0.3483(7) -0.2412(6) 0.9765(7) 0.0244(14) Uani 1 1 d . . . H1 H 0.3025 -0.3014 0.9517 0.029 Uiso 1 1 calc R . . N5 N 0.3387(8) -0.0433(6) 0.9527(8) 0.0159(9) Uani 1 1 d . . . O1 O 0.5419(5) -0.1724(4) 1.1260(16) 0.0444(18) Uani 1 1 d . . . C1 C 0.4895(6) -0.3629(4) 1.1290(19) 0.0208(9) Uani 1 1 d . . . H1A H 0.4288 -0.4158 1.0778 0.031 Uiso 1 1 calc R . . H1B H 0.4656 -0.3629 1.2328 0.031 Uiso 1 1 calc R . . H1C H 0.5899 -0.3834 1.1165 0.031 Uiso 1 1 calc R . . C2 C 0.4656(8) -0.2504(6) 1.0676(8) 0.0208(9) Uani 1 1 d . . . C3 C 0.3002(11) -0.1432(8) 0.9231(10) 0.0208(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 Mn1 0.0093(5) 0.0116(6) 0.0203(6) 0.000 0.000 0.0006(4) N3 0.011(3) 0.018(3) 0.020(3) 0.002(3) -0.003(3) 0.001(3) N4 0.0128(17) 0.0132(17) 0.022(2) -0.004(2) -0.0045(17) 0.004(3) N2 0.013(3) 0.019(3) 0.019(3) 0.006(2) 0.000(2) 0.003(2) N1 0.026(3) 0.021(3) 0.027(3) 0.002(3) -0.004(3) -0.001(3) N5 0.0128(17) 0.0132(17) 0.022(2) -0.004(2) -0.0045(17) 0.004(3) O1 0.0091(18) 0.015(2) 0.109(5) -0.025(5) -0.004(6) -0.0002(16) C1 0.024(2) 0.0084(18) 0.030(2) 0.0017(19) 0.002(2) -0.0003(14) C2 0.024(2) 0.0084(18) 0.030(2) 0.0017(19) 0.002(2) -0.0003(14) C3 0.024(2) 0.0084(18) 0.030(2) 0.0017(19) 0.002(2) -0.0003(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 Mn1 O1 2.136(5) 4_454 ? Mn1 O1 2.136(5) 3_554 ? Mn1 N5 2.259(8) 4_454 ? Mn1 N5 2.259(8) 3_554 ? Mn1 N3 2.264(8) . ? Mn1 N3 2.264(8) 2 ? N3 N4 1.237(12) . ? N3 N2 1.414(10) . ? N4 N5 1.405(11) . ? N2 C3 1.332(8) . ? N1 C3 1.367(11) . ? N1 C2 1.386(10) . ? N5 C3 1.297(11) . ? N5 Mn1 2.259(8) 3 ? O1 C2 1.305(10) . ? O1 Mn1 2.136(5) 3 ? C1 C2 1.498(11) . ? 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 Mn1 O1 179.9(8) 4_454 3_554 ? O1 Mn1 N5 83.8(4) 4_454 4_454 ? O1 Mn1 N5 96.1(4) 3_554 4_454 ? O1 Mn1 N5 96.1(4) 4_454 3_554 ? O1 Mn1 N5 83.8(4) 3_554 3_554 ? N5 Mn1 N5 90.2(4) 4_454 3_554 ? O1 Mn1 N3 94.6(4) 4_454 . ? O1 Mn1 N3 85.5(4) 3_554 . ? N5 Mn1 N3 177.5(4) 4_454 . ? N5 Mn1 N3 87.95(17) 3_554 . ? O1 Mn1 N3 85.5(4) 4_454 2 ? O1 Mn1 N3 94.6(4) 3_554 2 ? N5 Mn1 N3 87.95(17) 4_454 2 ? N5 Mn1 N3 177.5(4) 3_554 2 ? N3 Mn1 N3 93.9(4) . 2 ? N4 N3 N2 111.2(7) . . ? N4 N3 Mn1 131.2(6) . . ? N2 N3 Mn1 117.7(5) . . ? N3 N4 N5 109.2(4) . . ? C3 N2 N3 101.3(8) . . ? C3 N1 C2 123.3(7) . . ? C3 N5 N4 103.8(7) . . ? C3 N5 Mn1 123.6(7) . 3 ? N4 N5 Mn1 132.1(5) . 3 ? C2 O1 Mn1 128.0(6) . 3 ? O1 C2 N1 128.6(7) . . ? O1 C2 C1 115.4(8) . . ? N1 C2 C1 114.9(7) . . ? N5 C3 N2 114.4(10) . . ? N5 C3 N1 130.7(9) . . ? N2 C3 N1 114.9(9) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N4 0.88 2.33 3.180(9) 161.8 7_544 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.375 _refine_diff_density_min -0.696 _refine_diff_density_rms 0.167 data_compound5 _database_code_depnum_ccdc_archive 'CCDC 917091' #TrackingRef 'web_deposit_cif_file_8_Jian-ZhenLiao_1356326008.compound5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 Cd N10 O2' _chemical_formula_weight 392.68 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' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 9.4928(19) _cell_length_b 18.587(4) _cell_length_c 8.9107(18) _cell_angle_alpha 90.00 _cell_angle_beta 115.98(3) _cell_angle_gamma 90.00 _cell_volume 1413.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2631 _cell_measurement_theta_min 3.3577 _cell_measurement_theta_max 27.4546 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.845 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 1.568 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8815 _exptl_absorpt_correction_T_max 0.9281 _exptl_absorpt_process_details 'RAPID AUTO (Rigaku Corporation, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5833 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2475 _reflns_number_gt 2457 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-V (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0074P)^2^+3.1547P] 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 0.00(18) _refine_ls_number_reflns 2475 _refine_ls_number_parameters 191 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0231 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0481 _refine_ls_wR_factor_gt 0.0480 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.034 _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 Cd1 Cd 0.26906(5) 0.369976(10) 0.09242(5) 0.02791(7) Uani 1 1 d . . . N9 N 0.1009(5) 0.55663(18) 0.2286(4) 0.0374(8) Uani 1 1 d . . . N10 N 0.2164(4) 0.54919(16) 0.3868(4) 0.0323(8) Uani 1 1 d . . . N8 N 0.0846(5) 0.4979(2) 0.1472(4) 0.0422(9) Uani 1 1 d . . . N7 N 0.1901(4) 0.44856(18) 0.2465(4) 0.0379(8) Uani 1 1 d . . . N6 N 0.3833(5) 0.4492(2) 0.5284(4) 0.0419(9) Uani 1 1 d . . . H6 H 0.3912 0.4033 0.5232 0.050 Uiso 1 1 calc R . . O2 O 0.4861(4) 0.54672(17) 0.6975(4) 0.0541(9) Uani 1 1 d . . . O1 O 0.3959(4) 0.29315(16) -0.0257(4) 0.0484(8) Uani 1 1 d . . . N2 N 0.4109(4) 0.29386(16) 0.3012(4) 0.0323(8) Uani 1 1 d . . . N3 N 0.4416(5) 0.30425(19) 0.4631(4) 0.0420(9) Uani 1 1 d . . . N1 N 0.4887(5) 0.2012(2) 0.1619(4) 0.0361(8) Uani 1 1 d . . . H1 H 0.5181 0.1570 0.1735 0.043 Uiso 1 1 calc R . . N5 N 0.5608(4) 0.20657(17) 0.4530(4) 0.0337(8) Uani 1 1 d . . . N4 N 0.5304(5) 0.2530(2) 0.5531(4) 0.0423(9) Uani 1 1 d . . . C1 C 0.3251(10) 0.1616(5) -0.2501(11) 0.134(4) Uani 1 1 d . . . H1A H 0.3463 0.1310 -0.3247 0.201 Uiso 1 1 calc R . . H1B H 0.2683 0.2033 -0.3096 0.201 Uiso 1 1 calc R . . H1C H 0.2638 0.1358 -0.2064 0.201 Uiso 1 1 calc R . . C2 C 0.4725(6) 0.1840(3) -0.1132(5) 0.0532(13) Uani 1 1 d . . . H2A H 0.5343 0.2097 -0.1583 0.064 Uiso 1 1 calc R . . H2B H 0.5310 0.1416 -0.0561 0.064 Uiso 1 1 calc R . . C3 C 0.4493(5) 0.2317(2) 0.0114(5) 0.0392(10) Uani 1 1 d . . . C4 C 0.4862(5) 0.2349(2) 0.2997(4) 0.0305(8) Uani 1 1 d . . . C5 C 0.7462(9) 0.4297(6) 0.7723(12) 0.148(4) Uani 1 1 d . . . H5A H 0.8194 0.3968 0.8510 0.223 Uiso 1 1 calc R . . H5B H 0.7920 0.4768 0.7893 0.223 Uiso 1 1 calc R . . H5C H 0.7209 0.4139 0.6609 0.223 Uiso 1 1 calc R . . C6 C 0.6071(7) 0.4321(3) 0.7958(6) 0.0706(18) Uani 1 1 d . . . H6A H 0.6326 0.4483 0.9082 0.085 Uiso 1 1 calc R . . H6B H 0.5629 0.3841 0.7826 0.085 Uiso 1 1 calc R . . C7 C 0.4877(6) 0.4823(3) 0.6715(6) 0.0458(12) Uani 1 1 d . . . C8 C 0.2668(5) 0.4824(2) 0.3918(5) 0.0309(8) 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 Cd1 0.03719(12) 0.01687(11) 0.02386(10) 0.00102(18) 0.00801(8) 0.0007(2) N9 0.046(2) 0.0311(19) 0.0274(16) -0.0005(14) 0.0090(15) 0.0107(16) N10 0.047(2) 0.0193(16) 0.0256(15) -0.0040(12) 0.0112(15) 0.0059(14) N8 0.049(2) 0.035(2) 0.0318(18) -0.0056(15) 0.0070(16) 0.0134(18) N7 0.047(2) 0.0278(18) 0.0295(17) -0.0054(13) 0.0079(16) 0.0100(15) N6 0.055(2) 0.0259(19) 0.0320(18) -0.0016(14) 0.0071(17) 0.0133(17) O2 0.0441(19) 0.0395(18) 0.0516(19) -0.0141(15) -0.0040(15) 0.0096(15) O1 0.076(2) 0.0400(18) 0.0392(16) 0.0156(13) 0.0347(17) 0.0223(16) N2 0.047(2) 0.0218(17) 0.0228(15) 0.0053(12) 0.0105(14) 0.0104(15) N3 0.066(3) 0.0291(19) 0.0267(17) 0.0053(14) 0.0164(18) 0.0184(19) N1 0.058(2) 0.0249(19) 0.0266(17) 0.0070(14) 0.0192(17) 0.0180(18) N5 0.047(2) 0.0247(18) 0.0262(16) 0.0043(13) 0.0129(15) 0.0118(15) N4 0.062(3) 0.036(2) 0.0244(17) 0.0046(15) 0.0148(17) 0.0220(19) C1 0.107(7) 0.160(8) 0.146(8) -0.110(7) 0.066(6) -0.043(6) C2 0.077(4) 0.056(3) 0.035(2) 0.007(2) 0.033(3) 0.025(3) C3 0.049(3) 0.040(3) 0.034(2) 0.0072(18) 0.023(2) 0.015(2) C4 0.039(2) 0.025(2) 0.0257(19) 0.0024(14) 0.0124(16) 0.0055(16) C5 0.067(5) 0.176(10) 0.153(9) -0.001(7) 0.003(5) 0.049(6) C6 0.068(4) 0.065(4) 0.047(3) -0.007(3) -0.004(3) 0.033(3) C7 0.044(3) 0.044(3) 0.040(2) -0.0077(19) 0.010(2) 0.015(2) C8 0.036(2) 0.023(2) 0.0307(19) -0.0008(14) 0.0119(16) 0.0056(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 Cd1 N10 2.250(3) 2_564 ? Cd1 N2 2.254(3) . ? Cd1 N5 2.308(3) 4_454 ? Cd1 N7 2.341(3) . ? Cd1 O1 2.388(3) . ? Cd1 O2 2.414(3) 2_564 ? N9 N8 1.283(5) . ? N9 N10 1.362(4) . ? N10 C8 1.323(5) . ? N10 Cd1 2.250(3) 2_565 ? N8 N7 1.360(5) . ? N7 C8 1.333(5) . ? N6 C7 1.370(6) . ? N6 C8 1.381(5) . ? O2 C7 1.222(5) . ? O2 Cd1 2.414(3) 2_565 ? O1 C3 1.235(5) . ? N2 C4 1.312(5) . ? N2 N3 1.354(4) . ? N3 N4 1.292(5) . ? N1 C3 1.348(5) . ? N1 C4 1.388(5) . ? N5 C4 1.340(5) . ? N5 N4 1.360(5) . ? N5 Cd1 2.308(3) 4 ? C1 C2 1.457(9) . ? C2 C3 1.510(6) . ? C5 C6 1.425(11) . ? C6 C7 1.510(6) . ? 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 N10 Cd1 N2 158.52(13) 2_564 . ? N10 Cd1 N5 98.11(12) 2_564 4_454 ? N2 Cd1 N5 96.81(12) . 4_454 ? N10 Cd1 N7 92.68(12) 2_564 . ? N2 Cd1 N7 97.86(12) . . ? N5 Cd1 N7 106.36(13) 4_454 . ? N10 Cd1 O1 90.89(11) 2_564 . ? N2 Cd1 O1 75.77(11) . . ? N5 Cd1 O1 82.67(12) 4_454 . ? N7 Cd1 O1 169.70(12) . . ? N10 Cd1 O2 74.63(11) 2_564 2_564 ? N2 Cd1 O2 89.01(12) . 2_564 ? N5 Cd1 O2 171.33(12) 4_454 2_564 ? N7 Cd1 O2 79.07(13) . 2_564 ? O1 Cd1 O2 92.59(13) . 2_564 ? N8 N9 N10 110.0(3) . . ? C8 N10 N9 104.2(3) . . ? C8 N10 Cd1 130.6(3) . 2_565 ? N9 N10 Cd1 124.5(2) . 2_565 ? N9 N8 N7 109.5(3) . . ? C8 N7 N8 104.3(3) . . ? C8 N7 Cd1 133.3(3) . . ? N8 N7 Cd1 111.9(2) . . ? C7 N6 C8 126.4(4) . . ? C7 O2 Cd1 129.4(3) . 2_565 ? C3 O1 Cd1 131.5(3) . . ? C4 N2 N3 105.4(3) . . ? C4 N2 Cd1 130.4(3) . . ? N3 N2 Cd1 124.2(2) . . ? N4 N3 N2 109.5(3) . . ? C3 N1 C4 125.9(4) . . ? C4 N5 N4 104.5(3) . . ? C4 N5 Cd1 137.4(3) . 4 ? N4 N5 Cd1 114.6(2) . 4 ? N3 N4 N5 109.2(3) . . ? C1 C2 C3 112.8(5) . . ? O1 C3 N1 123.8(4) . . ? O1 C3 C2 121.4(4) . . ? N1 C3 C2 114.7(4) . . ? N2 C4 N5 111.4(3) . . ? N2 C4 N1 127.3(4) . . ? N5 C4 N1 121.3(4) . . ? C5 C6 C7 111.0(6) . . ? O2 C7 N6 123.5(4) . . ? O2 C7 C6 122.3(4) . . ? N6 C7 C6 114.2(4) . . ? N10 C8 N7 112.0(3) . . ? N10 C8 N6 125.9(3) . . ? N7 C8 N6 122.1(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 N6 H6 N3 0.86 2.03 2.862(5) 161.7 . N1 H1 N9 0.86 2.00 2.856(5) 173.3 3_545 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.484 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.060 data_compound6 _database_code_depnum_ccdc_archive 'CCDC 917092' #TrackingRef 'web_deposit_cif_file_0_Jian-ZhenLiao_1356326179.compound6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 Mn N10 O2' _chemical_formula_weight 335.22 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 9.811(2) _cell_length_b 18.035(4) _cell_length_c 8.8072(18) _cell_angle_alpha 90.00 _cell_angle_beta 117.44(3) _cell_angle_gamma 90.00 _cell_volume 1383.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2146 _cell_measurement_theta_min 3.4488 _cell_measurement_theta_max 27.4816 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.978 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9456 _exptl_absorpt_correction_T_max 0.9663 _exptl_absorpt_process_details 'RAPID AUTO (Rigaku Corporation, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD area-detector' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5681 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0694 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3028 _reflns_number_gt 2829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-V (Sheldrick, 1998)' _computing_publication_material 'SHELXL-97/2 (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^)+(0.0478P)^2^+12.8083P] 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 0.00(5) _refine_ls_number_reflns 3028 _refine_ls_number_parameters 191 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0747 _refine_ls_wR_factor_ref 0.1809 _refine_ls_wR_factor_gt 0.1766 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.128 _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 Mn1 Mn -0.86350(12) -0.36926(5) -0.40975(12) 0.0270(2) Uani 1 1 d . . . N1 N -0.9986(7) -0.2934(3) -0.6218(7) 0.0305(13) Uani 1 1 d . . . O2 O -1.0646(7) -0.4466(3) -0.5149(8) 0.0486(16) Uani 1 1 d . . . O1 O -0.9698(7) -0.2956(3) -0.2908(7) 0.0409(14) Uani 1 1 d . . . N2 N -1.0383(9) -0.3018(3) -0.7893(8) 0.0385(16) Uani 1 1 d . . . N3 N -1.1287(8) -0.2508(4) -0.8804(8) 0.0375(15) Uani 1 1 d . . . N4 N -1.1570(7) -0.2041(3) -0.7770(7) 0.0274(13) Uani 1 1 d . . . N5 N -1.0679(8) -0.1996(3) -0.4736(7) 0.0350(15) Uani 1 1 d . . . H5 H -1.0953 -0.1538 -0.4822 0.042 Uiso 1 1 calc R . . N6 N -0.7980(7) -0.4518(3) -0.2009(8) 0.0310(13) Uani 1 1 d . . . N7 N -0.6843(8) -0.4464(4) -0.0416(8) 0.0380(16) Uani 1 1 d . . . N10 N -0.9790(9) -0.5499(4) -0.3513(8) 0.0427(18) Uani 1 1 d . . . H10 H -0.9942 -0.5968 -0.3490 0.051 Uiso 1 1 calc R . . N8 N -0.6756(8) -0.5064(4) 0.0418(9) 0.0407(17) Uani 1 1 d . . . C1 C -1.0742(8) -0.2329(4) -0.6194(9) 0.0277(14) Uani 1 1 d . . . C2 C -1.0226(10) -0.2325(4) -0.3192(11) 0.0390(18) Uani 1 1 d . . . C3 C -1.0402(12) -0.1870(5) -0.1883(12) 0.051(2) Uani 1 1 d . . . H3A H -1.1112 -0.2117 -0.1566 0.061 Uiso 1 1 calc R . . H3B H -1.0844 -0.1394 -0.2380 0.061 Uiso 1 1 calc R . . C4 C -0.8893(17) -0.1741(10) -0.0281(17) 0.105(5) Uani 1 1 d . . . H4A H -0.9076 -0.1447 0.0516 0.157 Uiso 1 1 calc R . . H4B H -0.8193 -0.1485 -0.0580 0.157 Uiso 1 1 calc R . . H4C H -0.8458 -0.2209 0.0231 0.157 Uiso 1 1 calc R . . C5 C -0.8575(8) -0.5186(4) -0.2097(9) 0.0280(15) Uani 1 1 d . . . C6 C -1.0750(9) -0.5121(4) -0.4923(10) 0.0376(18) Uani 1 1 d . . . C7 C -1.2053(13) -0.5591(6) -0.6217(12) 0.060(3) Uani 1 1 d . . . H7A H -1.1679 -0.6088 -0.6230 0.072 Uiso 1 1 calc R . . H7B H -1.2409 -0.5380 -0.7350 0.072 Uiso 1 1 calc R . . C8 C -1.3378(14) -0.5631(9) -0.5785(17) 0.098(5) Uani 1 1 d . . . H8A H -1.4184 -0.5930 -0.6620 0.147 Uiso 1 1 calc R . . H8B H -1.3759 -0.5140 -0.5788 0.147 Uiso 1 1 calc R . . H8C H -1.3030 -0.5847 -0.4672 0.147 Uiso 1 1 calc R . . N9 N -0.7842(8) -0.5551(3) -0.0601(8) 0.0352(15) 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 Mn1 0.0334(5) 0.0173(4) 0.0230(4) 0.0006(5) 0.0069(3) 0.0000(5) N1 0.045(4) 0.019(3) 0.026(3) 0.004(2) 0.015(3) 0.010(2) O2 0.046(3) 0.034(3) 0.047(3) 0.006(3) 0.005(3) -0.011(3) O1 0.061(4) 0.035(3) 0.033(3) 0.011(2) 0.028(3) 0.018(3) N2 0.061(5) 0.027(3) 0.026(3) 0.006(3) 0.018(3) 0.018(3) N3 0.045(4) 0.035(3) 0.026(3) 0.006(3) 0.011(3) 0.018(3) N4 0.029(3) 0.022(3) 0.025(3) 0.001(2) 0.008(2) 0.006(2) N5 0.054(4) 0.025(3) 0.024(3) 0.003(2) 0.015(3) 0.016(3) N6 0.039(3) 0.020(3) 0.026(3) 0.002(2) 0.008(3) -0.005(2) N7 0.043(4) 0.030(3) 0.029(3) 0.003(3) 0.006(3) -0.010(3) N10 0.062(5) 0.022(3) 0.028(3) 0.004(2) 0.008(3) -0.012(3) N8 0.038(4) 0.036(4) 0.033(3) 0.007(3) 0.004(3) -0.013(3) C1 0.032(3) 0.021(3) 0.028(3) 0.002(2) 0.012(3) 0.003(3) C2 0.044(4) 0.035(4) 0.036(4) 0.007(3) 0.017(4) 0.008(3) C3 0.077(7) 0.047(5) 0.044(5) 0.005(4) 0.040(5) 0.028(5) C4 0.102(12) 0.132(13) 0.075(9) -0.053(9) 0.036(9) -0.028(10) C5 0.036(4) 0.022(3) 0.026(3) 0.006(3) 0.015(3) -0.006(3) C6 0.036(4) 0.038(4) 0.030(4) 0.007(3) 0.008(3) -0.008(3) C7 0.068(7) 0.055(6) 0.035(5) -0.002(4) 0.004(5) -0.031(5) C8 0.053(7) 0.122(12) 0.089(10) 0.015(9) 0.007(7) -0.042(8) N9 0.041(4) 0.024(3) 0.030(3) 0.006(2) 0.007(3) -0.006(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 Mn1 N1 2.199(6) . ? Mn1 N6 2.218(6) . ? Mn1 O1 2.227(5) . ? Mn1 O2 2.238(6) . ? Mn1 N4 2.245(6) 4_545 ? Mn1 N9 2.274(6) 2_544 ? N1 C1 1.326(9) . ? N1 N2 1.349(9) . ? O2 C6 1.210(9) . ? O1 C2 1.227(9) . ? N2 N3 1.274(9) . ? N3 N4 1.359(9) . ? N4 C1 1.348(9) . ? N4 Mn1 2.245(6) 4_444 ? N5 C2 1.357(9) . ? N5 C1 1.393(9) . ? N6 C5 1.326(8) . ? N6 N7 1.334(8) . ? N7 N8 1.288(9) . ? N10 C6 1.348(10) . ? N10 C5 1.388(9) . ? N8 N9 1.354(9) . ? C2 C3 1.489(11) . ? C3 C4 1.520(16) . ? C5 N9 1.346(9) . ? C6 C7 1.520(11) . ? C7 C8 1.515(17) . ? N9 Mn1 2.274(6) 2_545 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Mn1 N6 162.3(2) . . ? N1 Mn1 O1 78.4(2) . . ? N6 Mn1 O1 91.7(2) . . ? N1 Mn1 O2 88.0(2) . . ? N6 Mn1 O2 77.8(2) . . ? O1 Mn1 O2 93.0(3) . . ? N1 Mn1 N4 97.0(2) . 4_545 ? N6 Mn1 N4 96.7(2) . 4_545 ? O1 Mn1 N4 84.8(2) . 4_545 ? O2 Mn1 N4 174.0(2) . 4_545 ? N1 Mn1 N9 96.5(2) . 2_544 ? N6 Mn1 N9 92.0(2) . 2_544 ? O1 Mn1 N9 172.9(2) . 2_544 ? O2 Mn1 N9 81.8(3) . 2_544 ? N4 Mn1 N9 100.8(2) 4_545 2_544 ? C1 N1 N2 103.2(6) . . ? C1 N1 Mn1 128.4(5) . . ? N2 N1 Mn1 128.0(4) . . ? C6 O2 Mn1 131.7(6) . . ? C2 O1 Mn1 134.6(5) . . ? N3 N2 N1 111.9(6) . . ? N2 N3 N4 108.9(6) . . ? C1 N4 N3 103.9(5) . . ? C1 N4 Mn1 137.2(5) . 4_444 ? N3 N4 Mn1 115.5(4) . 4_444 ? C2 N5 C1 126.1(6) . . ? C5 N6 N7 105.1(6) . . ? C5 N6 Mn1 127.6(5) . . ? N7 N6 Mn1 127.3(4) . . ? N8 N7 N6 110.0(6) . . ? C6 N10 C5 124.6(6) . . ? N7 N8 N9 110.0(6) . . ? N1 C1 N4 112.1(6) . . ? N1 C1 N5 125.6(6) . . ? N4 C1 N5 122.3(6) . . ? O1 C2 N5 121.6(7) . . ? O1 C2 C3 122.8(7) . . ? N5 C2 C3 115.7(7) . . ? C2 C3 C4 113.1(9) . . ? N6 C5 N9 111.4(6) . . ? N6 C5 N10 126.5(6) . . ? N9 C5 N10 122.1(6) . . ? O2 C6 N10 124.8(7) . . ? O2 C6 C7 121.8(7) . . ? N10 C6 C7 113.4(7) . . ? C6 C7 C8 111.1(9) . . ? C5 N9 N8 103.5(6) . . ? C5 N9 Mn1 133.7(5) . 2_545 ? N8 N9 Mn1 112.3(5) . 2_545 ? 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 N5 H5 N7 0.86 1.97 2.822(9) 170.2 4_444 N10 H10 N2 0.86 2.00 2.842(9) 164.5 2_545 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.152 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.116