# 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_p091215b _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H8 Co N14, 2(O)' _chemical_formula_sum 'C8 H8 Co N14 O2' _chemical_formula_weight 391.22 _chemical_melting_point ? 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' Co Co 0.3494 0.9721 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1994(16) _cell_length_b 16.883(3) _cell_length_c 12.655(4) _cell_angle_alpha 90 _cell_angle_beta 129.974(19) _cell_angle_gamma 90 _cell_volume 1342.5(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 153(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 1.325 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.931 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description ? _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.01 _exptl_special_details ; ? ; _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0373 _diffrn_reflns_av_unetI/netI 0.0644 _diffrn_reflns_Laue_measured_fraction_full 0.839 _diffrn_reflns_Laue_measured_fraction_max 0.867 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3495 _diffrn_reflns_point_group_measured_fraction_full 0.839 _diffrn_reflns_point_group_measured_fraction_max 0.867 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.004 _diffrn_reflns_theta_min 2.762 _diffrn_ambient_temperature 153(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.839 _diffrn_measured_fraction_theta_max 0.867 _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source ? _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1603 _reflns_number_total 2047 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution ? _refine_diff_density_max 1.269 _refine_diff_density_min -2.584 _refine_diff_density_rms 0.229 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 235 _refine_ls_number_reflns 2047 _refine_ls_number_restraints 108 _refine_ls_R_factor_all 0.1349 _refine_ls_R_factor_gt 0.1184 _refine_ls_restrained_S_all 0.948 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0001P)^2^+107.1204P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2687 _refine_ls_wR_factor_ref 0.2759 _refine_special_details ; ? ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary ? _atom_sites_solution_secondary ? 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.5196(2) 0.74690(11) 0.37554(18) 0.0081(5) Uani 1 1 d . . . . . C1 C 0.5690(18) 0.7364(7) 0.6425(13) 0.0089(13) Uani 1 1 d . U . . . C2 C 0.696(2) 0.6654(8) 0.6814(13) 0.011(3) Uani 1 1 d . U . . . C3 C 0.866(2) 0.6362(8) 0.8105(15) 0.016(3) Uani 1 1 d . U . . . H3 H 0.9162 0.6562 0.8952 0.020 Uiso 1 1 calc R U . . . C4 C 0.689(2) 0.6125(8) 0.5897(15) 0.017(3) Uani 1 1 d . . . . . C5 C 0.0378(19) 0.7670(8) 0.1099(14) 0.013(3) Uani 1 1 d . . . . . C6 C 0.092(2) 0.8396(8) 0.0770(14) 0.011(3) Uani 1 1 d . U . . . C7 C -0.005(2) 0.8742(8) -0.0527(13) 0.014(3) Uani 1 1 d . . . . . H7 H -0.1275 0.8568 -0.1376 0.016 Uiso 1 1 calc R U . . . C8 C 0.277(2) 0.8853(8) 0.1655(14) 0.015(3) Uani 1 1 d . . . . . N1 N 0.4832(16) 0.7702(6) 0.5230(11) 0.0089(12) Uani 1 1 d . U . . . N2 N 0.3851(16) 0.8374(6) 0.5224(11) 0.0090(13) Uani 1 1 d . U . . . N3 N 0.4160(17) 0.8420(7) 0.6366(11) 0.013(2) Uani 1 1 d . . . . . N4 N 0.5343(16) 0.7778(6) 0.7143(11) 0.0090(13) Uani 1 1 d . U . . . N5 N 0.942(2) 0.5742(8) 0.7898(12) 0.029(4) Uani 1 1 d . . . . . H5 H 1.0515 0.5478 0.8562 0.035 Uiso 1 1 calc R U . . . N6 N 0.8344(19) 0.5563(7) 0.6559(11) 0.020(3) Uani 1 1 d . . . . . N7 N 0.5529(19) 0.6207(7) 0.4461(11) 0.020(3) Uani 1 1 d . . . . . H7A H 0.4132 0.6007 0.4068 0.024 Uiso 1 1 calc R U . . . H7B H 0.6067 0.5885 0.4110 0.024 Uiso 1 1 calc R U . . . N8 N 0.1886(16) 0.7269(6) 0.2270(11) 0.0104(14) Uani 1 1 d . U . . . N9 N 0.0890(16) 0.6623(6) 0.2253(11) 0.0106(14) Uani 1 1 d . U . . . N10 N -0.1104(16) 0.6646(6) 0.1137(11) 0.0109(14) Uani 1 1 d . U . . . N11 N -0.1452(16) 0.7298(6) 0.0400(12) 0.013(3) Uani 1 1 d . . . . . N12 N 0.1134(18) 0.9364(7) -0.0302(12) 0.017(3) Uani 1 1 d . . . . . H12 H 0.0820 0.9681 -0.0940 0.020 Uiso 1 1 calc R U . . . N13 N 0.2888(17) 0.9444(7) 0.1045(12) 0.015(3) Uani 1 1 d . . . . . N14 N 0.4387(17) 0.8737(6) 0.3121(11) 0.012(3) Uani 1 1 d . . . . . H14A H 0.3906 0.8973 0.3578 0.015 Uiso 1 1 calc R U . . . H14B H 0.5667 0.9014 0.3437 0.015 Uiso 1 1 calc R U . . . O1 O 0.709(2) 0.5237(8) 0.1195(14) 0.047(3) Uani 1 1 d . U . . . O2 O 0.990(4) 0.7464(13) 0.376(3) 0.030(5) Uani 0.5 1 d . U P . . O3 O 0.224(3) 0.9921(12) 0.584(2) 0.021(5) Uani 0.5 1 d . U P . . 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 Co1 0.0050(8) 0.0151(9) 0.0039(8) 0.0000(7) 0.0026(7) 0.0003(7) C1 0.0090(13) 0.0092(14) 0.0088(13) -0.0002(7) 0.0059(9) 0.0002(7) C2 0.010(4) 0.013(5) 0.008(4) -0.003(4) 0.006(3) 0.002(3) C3 0.016(3) 0.016(3) 0.016(3) -0.0001(10) 0.010(2) 0.0003(10) C4 0.022(7) 0.011(7) 0.021(8) -0.004(6) 0.014(7) -0.003(6) C5 0.007(6) 0.020(7) 0.010(7) -0.005(6) 0.005(5) 0.000(5) C6 0.012(3) 0.011(3) 0.011(3) 0.0002(10) 0.0072(19) 0.0000(10) C7 0.017(7) 0.012(7) 0.005(6) -0.003(5) 0.004(6) -0.002(5) C8 0.012(6) 0.019(7) 0.013(7) 0.006(6) 0.007(6) 0.005(5) N1 0.0091(13) 0.0090(13) 0.0088(13) -0.0001(7) 0.0058(9) 0.0001(7) N2 0.0091(14) 0.0089(14) 0.0087(14) -0.0001(8) 0.0057(10) 0.0001(8) N3 0.017(6) 0.014(6) 0.007(5) -0.001(5) 0.007(5) 0.000(5) N4 0.0092(14) 0.0092(14) 0.0088(14) 0.0001(8) 0.0059(10) 0.0001(8) N5 0.025(7) 0.031(8) 0.006(6) 0.002(5) -0.001(6) 0.020(6) N6 0.020(6) 0.023(7) 0.003(5) 0.000(5) 0.001(5) 0.013(5) N7 0.017(6) 0.021(6) 0.007(6) -0.006(5) 0.000(5) 0.000(5) N8 0.0105(15) 0.0106(16) 0.0102(16) 0.0003(8) 0.0067(10) -0.0004(8) N9 0.0107(15) 0.0106(15) 0.0103(15) 0.0003(7) 0.0067(10) -0.0002(7) N10 0.0110(15) 0.0108(16) 0.0106(16) 0.0003(8) 0.0067(10) -0.0001(8) N11 0.006(5) 0.009(6) 0.014(6) 0.008(4) 0.002(5) -0.001(4) N12 0.024(6) 0.020(6) 0.010(6) 0.005(5) 0.013(6) 0.001(5) N13 0.010(5) 0.010(6) 0.011(6) -0.001(5) 0.001(5) -0.002(4) N14 0.015(6) 0.012(6) 0.005(5) -0.001(4) 0.004(5) -0.002(4) O1 0.046(4) 0.044(4) 0.047(4) 0.001(2) 0.029(3) 0.000(2) O2 0.031(5) 0.028(5) 0.028(5) 0.000(2) 0.018(3) 0.000(2) O3 0.021(5) 0.020(5) 0.021(5) -0.001(2) 0.013(3) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N1 2.107(11) . ? Co1 N4 2.160(12) 4_575 ? Co1 N7 2.258(13) . ? Co1 N8 2.112(11) . ? Co1 N11 2.166(10) 4_676 ? Co1 N14 2.232(11) . ? C1 C2 1.451(17) . ? C1 N1 1.319(17) . ? C1 N4 1.315(17) . ? C2 C3 1.388(19) . ? C2 C4 1.433(19) . ? C3 H3 0.9300 . ? C3 N5 1.331(19) . ? C4 N6 1.321(18) . ? C4 N7 1.401(18) . ? C5 C6 1.455(19) . ? C5 N8 1.352(17) . ? C5 N11 1.312(17) . ? C6 C7 1.411(18) . ? C6 C8 1.402(19) . ? C7 H7 0.9300 . ? C7 N12 1.328(18) . ? C8 N13 1.301(18) . ? C8 N14 1.442(17) . ? N1 N2 1.388(15) . ? N2 N3 1.299(16) . ? N3 N4 1.363(15) . ? N4 Co1 2.160(12) 4_576 ? N5 H5 0.8600 . ? N5 N6 1.349(17) . ? N7 H7A 0.9700 . ? N7 H7B 0.9700 . ? N8 N9 1.354(15) . ? N9 N10 1.305(15) . ? N10 N11 1.350(15) . ? N11 Co1 2.166(10) 4_475 ? N12 H12 0.8600 . ? N12 N13 1.357(16) . ? N14 H14A 0.9700 . ? N14 H14B 0.9700 . ? 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 Co1 N4 176.2(4) . 4_575 ? N1 Co1 N7 82.9(4) . . ? N1 Co1 N8 89.2(4) . . ? N1 Co1 N11 86.0(4) . 4_676 ? N1 Co1 N14 87.8(4) . . ? N4 Co1 N7 97.2(4) 4_575 . ? N4 Co1 N11 97.8(4) 4_575 4_676 ? N4 Co1 N14 91.7(4) 4_575 . ? N8 Co1 N4 87.0(4) . 4_575 ? N8 Co1 N7 87.8(4) . . ? N8 Co1 N11 175.1(5) . 4_676 ? N8 Co1 N14 85.3(4) . . ? N11 Co1 N7 92.0(4) 4_676 . ? N11 Co1 N14 94.1(4) 4_676 . ? N14 Co1 N7 168.4(5) . . ? N1 C1 C2 118.9(12) . . ? N4 C1 C2 129.2(12) . . ? N4 C1 N1 111.7(11) . . ? C3 C2 C1 130.6(12) . . ? C3 C2 C4 102.8(12) . . ? C4 C2 C1 126.3(12) . . ? C2 C3 H3 126.6 . . ? N5 C3 C2 106.8(13) . . ? N5 C3 H3 126.6 . . ? N6 C4 C2 112.6(13) . . ? N6 C4 N7 122.3(13) . . ? N7 C4 C2 125.0(13) . . ? N8 C5 C6 120.1(11) . . ? N11 C5 C6 129.7(12) . . ? N11 C5 N8 110.2(12) . . ? C7 C6 C5 129.4(12) . . ? C8 C6 C5 127.5(12) . . ? C8 C6 C7 102.4(12) . . ? C6 C7 H7 126.6 . . ? N12 C7 C6 106.8(11) . . ? N12 C7 H7 126.6 . . ? C6 C8 N14 125.6(13) . . ? N13 C8 C6 113.6(12) . . ? N13 C8 N14 120.7(12) . . ? C1 N1 Co1 131.3(9) . . ? C1 N1 N2 103.8(10) . . ? N2 N1 Co1 124.0(8) . . ? N3 N2 N1 110.2(10) . . ? N2 N3 N4 107.2(10) . . ? C1 N4 Co1 136.0(9) . 4_576 ? C1 N4 N3 107.0(11) . . ? N3 N4 Co1 112.9(8) . 4_576 ? C3 N5 H5 122.8 . . ? C3 N5 N6 114.3(12) . . ? N6 N5 H5 122.8 . . ? C4 N6 N5 103.4(12) . . ? Co1 N7 H7A 108.8 . . ? Co1 N7 H7B 108.8 . . ? C4 N7 Co1 113.6(9) . . ? C4 N7 H7A 108.8 . . ? C4 N7 H7B 108.8 . . ? H7A N7 H7B 107.7 . . ? C5 N8 Co1 130.0(9) . . ? C5 N8 N9 105.5(10) . . ? N9 N8 Co1 124.0(8) . . ? N10 N9 N8 108.5(10) . . ? N9 N10 N11 109.5(10) . . ? C5 N11 Co1 139.2(9) . 4_475 ? C5 N11 N10 106.4(10) . . ? N10 N11 Co1 112.7(8) . 4_475 ? C7 N12 H12 123.6 . . ? C7 N12 N13 112.7(11) . . ? N13 N12 H12 123.6 . . ? C8 N13 N12 104.3(11) . . ? Co1 N14 H14A 108.7 . . ? Co1 N14 H14B 108.7 . . ? C8 N14 Co1 114.1(8) . . ? C8 N14 H14A 108.7 . . ? C8 N14 H14B 108.7 . . ? H14A N14 H14B 107.6 . . ? _shelx_estimated_absorpt_T_max 0.987 _shelx_estimated_absorpt_T_min 0.778 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-2 _database_code_depnum_ccdc_archive 'CCDC 920058' ####################################################################### # # 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_p090928q _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 N14 O3 Zn' _chemical_formula_weight 417.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2502(7) _cell_length_b 16.8656(10) _cell_length_c 12.7981(10) _cell_angle_alpha 90.00 _cell_angle_beta 129.908(5) _cell_angle_gamma 90.00 _cell_volume 1366.00(18) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.031 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.854 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5242 _exptl_absorpt_correction_T_max 0.9130 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9219 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2323 _reflns_number_gt 2022 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0075P)^2^+97.1534P] 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 2323 _refine_ls_number_parameters 245 _refine_ls_number_restraints 102 _refine_ls_R_factor_all 0.1195 _refine_ls_R_factor_gt 0.1135 _refine_ls_wR_factor_ref 0.2821 _refine_ls_wR_factor_gt 0.2805 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_restrained_S_all 1.153 _refine_ls_shift/su_max 0.168 _refine_ls_shift/su_mean 0.008 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 0.7787(2) 0.75154(9) 0.12559(15) 0.0082(4) Uani 1 1 d . . . C1 C 0.290(2) 0.7625(7) -0.1430(13) 0.010(3) Uani 1 1 d . . . C2 C 0.343(2) 0.8328(8) -0.1807(13) 0.012(3) Uani 1 1 d . . . C3 C 0.514(2) 0.8855(8) -0.0900(14) 0.014(3) Uani 1 1 d . . . C4 C 0.258(2) 0.8608(8) -0.3083(14) 0.013(3) Uani 1 1 d . . . H4 H 0.1402 0.8409 -0.3916 0.015 Uiso 1 1 calc R . . C5 C 0.8240(19) 0.7334(7) 0.3904(13) 0.0099(12) Uani 1 1 d U . . C6 C 0.948(2) 0.6605(8) 0.4243(13) 0.0102(13) Uani 1 1 d U . . C7 C 0.950(2) 0.6130(8) 0.3349(14) 0.014(3) Uani 1 1 d . . . C8 C 1.102(2) 0.6260(8) 0.5520(14) 0.014(3) Uani 1 1 d . . . H8 H 1.1450 0.6433 0.6354 0.017 Uiso 1 1 calc R . . N1 N 0.4402(16) 0.7271(6) -0.0232(10) 0.0081(16) Uani 1 1 d U . . N2 N 0.3448(16) 0.6625(6) -0.0207(10) 0.0081(16) Uani 1 1 d U . . N3 N 0.1489(17) 0.6586(7) -0.1350(11) 0.012(2) Uani 1 1 d . . . N4 N 0.1098(17) 0.7228(6) -0.2144(11) 0.010(2) Uani 1 1 d . . . N5 N 0.3758(18) 0.9211(7) -0.2897(11) 0.019(3) Uani 1 1 d . . . H5 H 0.3562 0.9462 -0.3555 0.022 Uiso 1 1 calc R . . N6 N 0.5328(19) 0.9397(6) -0.1551(12) 0.014(2) Uani 1 1 d . . . N7 N 0.6646(18) 0.8801(7) 0.0537(11) 0.015(3) Uani 1 1 d . . . H7A H 0.6066 0.8982 0.0894 0.018 Uiso 1 1 calc R . . H7B H 0.7762 0.9111 0.0846 0.018 Uiso 1 1 calc R . . N8 N 0.7406(17) 0.7734(6) 0.2731(11) 0.0099(12) Uani 1 1 d U . . N9 N 0.6418(17) 0.8378(6) 0.2745(10) 0.009(2) Uani 1 1 d . . . N10 N 0.6706(17) 0.8362(6) 0.3863(11) 0.0104(12) Uani 1 1 d U . . N11 N 0.7846(17) 0.7708(6) 0.4617(11) 0.0100(12) Uani 1 1 d U . . N12 N 1.1747(18) 0.5632(7) 0.5299(11) 0.016(3) Uani 1 1 d . . . H12 H 1.2694 0.5316 0.5932 0.019 Uiso 1 1 calc R . . N13 N 1.0835(19) 0.5546(7) 0.3972(12) 0.017(3) Uani 1 1 d . . . N14 N 0.8205(16) 0.6259(6) 0.1894(10) 0.009(2) Uani 1 1 d . . . H14A H 0.6921 0.6047 0.1479 0.010 Uiso 1 1 calc R . . H14B H 0.8791 0.5995 0.1598 0.010 Uiso 1 1 calc R . . O1 O 0.4568(19) 0.9748(8) 0.3723(12) 0.036(3) Uani 1 1 d U . . O2 O 0.046(2) 0.9905(8) 0.4064(14) 0.044(3) Uani 1 1 d U . . O3 O 0.252(9) 0.752(3) 0.120(5) 0.108(8) Uani 0.50(4) 1 d PU A 1 O3' O 0.125(8) 0.748(3) 0.128(5) 0.108(8) Uani 0.50(4) 1 d PU A 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 0.0069(7) 0.0125(8) 0.0046(7) -0.0002(6) 0.0033(6) -0.0002(6) C1 0.012(6) 0.008(6) 0.011(6) -0.006(5) 0.008(6) -0.007(5) C2 0.015(7) 0.010(6) 0.010(6) 0.005(5) 0.007(6) 0.000(5) C3 0.016(7) 0.008(6) 0.021(7) -0.004(6) 0.013(6) 0.000(5) C4 0.008(6) 0.015(7) 0.011(6) -0.001(5) 0.004(6) -0.006(5) C5 0.0100(12) 0.0102(12) 0.0100(12) 0.0001(6) 0.0065(8) 0.0001(6) C6 0.0102(14) 0.0102(14) 0.0101(14) 0.0002(8) 0.0064(9) 0.0000(8) C7 0.016(7) 0.016(7) 0.015(7) 0.003(6) 0.012(6) -0.001(6) C8 0.020(7) 0.011(7) 0.010(6) -0.001(5) 0.010(6) 0.002(5) N1 0.0081(17) 0.0082(17) 0.0080(17) 0.0001(8) 0.0051(12) -0.0002(8) N2 0.0082(17) 0.0081(17) 0.0080(17) 0.0002(8) 0.0052(12) -0.0002(8) N3 0.012(5) 0.014(6) 0.007(5) 0.004(4) 0.005(5) 0.001(4) N4 0.008(5) 0.007(5) 0.011(5) 0.002(4) 0.005(5) 0.001(4) N5 0.017(6) 0.023(7) 0.004(5) 0.003(5) 0.002(5) -0.008(5) N6 0.021(6) 0.007(5) 0.013(6) 0.000(4) 0.012(5) -0.003(5) N7 0.014(6) 0.024(6) 0.007(5) -0.004(5) 0.006(5) -0.005(5) N8 0.0100(14) 0.0101(14) 0.0099(13) 0.0000(8) 0.0065(9) 0.0002(8) N9 0.010(5) 0.011(5) 0.003(5) 0.000(4) 0.002(4) 0.003(4) N10 0.0104(14) 0.0102(14) 0.0102(14) 0.0001(8) 0.0065(9) 0.0001(8) N11 0.0102(13) 0.0101(13) 0.0100(13) 0.0001(7) 0.0066(9) 0.0001(7) N12 0.018(6) 0.014(6) 0.010(5) 0.005(5) 0.006(5) 0.011(5) N13 0.023(6) 0.013(6) 0.016(6) 0.002(5) 0.014(6) 0.007(5) N14 0.005(5) 0.010(5) 0.009(5) -0.001(4) 0.004(5) 0.002(4) O1 0.036(3) 0.036(3) 0.036(3) 0.0002(10) 0.023(2) 0.0002(10) O2 0.044(3) 0.044(3) 0.044(3) 0.0001(10) 0.029(2) 0.0005(10) O3 0.108(8) 0.108(8) 0.108(8) 0.0000(8) 0.069(5) 0.0000(8) O3' 0.108(8) 0.108(8) 0.108(8) 0.0000(8) 0.069(5) 0.0000(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N8 2.136(11) . ? Zn1 N4 2.160(11) 4_676 ? Zn1 N11 2.162(11) 4_575 ? Zn1 N1 2.185(10) . ? Zn1 N14 2.217(11) . ? Zn1 N7 2.307(12) . ? C1 N4 1.325(17) . ? C1 N1 1.343(17) . ? C1 C2 1.447(18) . ? C2 C4 1.383(18) . ? C2 C3 1.426(19) . ? C3 N6 1.311(18) . ? C3 N7 1.415(18) . ? C4 N5 1.317(18) . ? C4 H4 0.9300 . ? C5 N11 1.311(17) . ? C5 N8 1.362(16) . ? C5 C6 1.475(17) . ? C6 C8 1.400(18) . ? C6 C7 1.404(19) . ? C7 N13 1.303(18) . ? C7 N14 1.450(17) . ? C8 N12 1.333(18) . ? C8 H8 0.9300 . ? N1 N2 1.355(15) . ? N2 N3 1.312(15) . ? N3 N4 1.375(15) . ? N4 Zn1 2.160(11) 4_475 ? N5 N6 1.371(16) . ? N5 H5 0.8600 . ? N7 H7A 0.9000 . ? N7 H7B 0.9000 . ? N8 N9 1.364(15) . ? N9 N10 1.292(15) . ? N10 N11 1.367(15) . ? N11 Zn1 2.162(11) 4_576 ? N12 N13 1.354(16) . ? N12 H12 0.8600 . ? N14 H14A 0.9000 . ? N14 H14B 0.9000 . ? 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 N8 Zn1 N4 86.6(4) . 4_676 ? N8 Zn1 N11 174.5(4) . 4_575 ? N4 Zn1 N11 98.8(4) 4_676 4_575 ? N8 Zn1 N1 88.4(4) . . ? N4 Zn1 N1 175.0(4) 4_676 . ? N11 Zn1 N1 86.2(4) 4_575 . ? N8 Zn1 N14 85.2(4) . . ? N4 Zn1 N14 92.2(4) 4_676 . ? N11 Zn1 N14 95.5(4) 4_575 . ? N1 Zn1 N14 87.1(4) . . ? N8 Zn1 N7 86.4(4) . . ? N4 Zn1 N7 97.7(4) 4_676 . ? N11 Zn1 N7 92.0(4) 4_575 . ? N1 Zn1 N7 82.2(4) . . ? N14 Zn1 N7 166.5(4) . . ? N4 C1 N1 111.5(11) . . ? N4 C1 C2 128.9(12) . . ? N1 C1 C2 119.5(11) . . ? C4 C2 C3 103.5(12) . . ? C4 C2 C1 129.9(12) . . ? C3 C2 C1 126.3(12) . . ? N6 C3 N7 120.6(12) . . ? N6 C3 C2 112.1(12) . . ? N7 C3 C2 127.1(13) . . ? N5 C4 C2 107.1(12) . . ? N5 C4 H4 126.4 . . ? C2 C4 H4 126.4 . . ? N11 C5 N8 110.6(11) . . ? N11 C5 C6 129.2(12) . . ? N8 C5 C6 120.1(12) . . ? C8 C6 C7 103.8(12) . . ? C8 C6 C5 129.0(12) . . ? C7 C6 C5 127.1(12) . . ? N13 C7 C6 112.4(12) . . ? N13 C7 N14 122.3(13) . . ? C6 C7 N14 125.3(12) . . ? N12 C8 C6 106.1(12) . . ? N12 C8 H8 127.0 . . ? C6 C8 H8 127.0 . . ? C1 N1 N2 105.2(10) . . ? C1 N1 Zn1 129.5(9) . . ? N2 N1 Zn1 124.6(8) . . ? N3 N2 N1 109.5(10) . . ? N2 N3 N4 108.7(10) . . ? C1 N4 N3 105.2(10) . . ? C1 N4 Zn1 137.0(9) . 4_475 ? N3 N4 Zn1 114.4(8) . 4_475 ? C4 N5 N6 113.4(11) . . ? C4 N5 H5 123.3 . . ? N6 N5 H5 123.3 . . ? C3 N6 N5 103.7(11) . . ? C3 N7 Zn1 111.8(8) . . ? C3 N7 H7A 109.2 . . ? Zn1 N7 H7A 109.2 . . ? C3 N7 H7B 109.2 . . ? Zn1 N7 H7B 109.2 . . ? H7A N7 H7B 107.9 . . ? C5 N8 N9 105.3(10) . . ? C5 N8 Zn1 129.1(9) . . ? N9 N8 Zn1 125.2(8) . . ? N10 N9 N8 108.2(10) . . ? N9 N10 N11 110.6(10) . . ? C5 N11 N10 105.2(10) . . ? C5 N11 Zn1 139.6(9) . 4_576 ? N10 N11 Zn1 113.1(8) . 4_576 ? C8 N12 N13 112.9(11) . . ? C8 N12 H12 123.6 . . ? N13 N12 H12 123.6 . . ? C7 N13 N12 104.8(11) . . ? C7 N14 Zn1 115.4(8) . . ? C7 N14 H14A 108.4 . . ? Zn1 N14 H14A 108.4 . . ? C7 N14 H14B 108.4 . . ? Zn1 N14 H14B 108.4 . . ? H14A N14 H14B 107.5 . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.905 _refine_diff_density_min -4.460 _refine_diff_density_rms 0.304 _database_code_depnum_ccdc_archive 'CCDC 920059' ####################################################################### # # 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_p091013k #TrackingRef 'P091013K.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H3 Cu0.50 N7' _chemical_formula_weight 180.91 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.6277(6) _cell_length_b 6.4382(4) _cell_length_c 9.7615(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.393(5) _cell_angle_gamma 90.00 _cell_volume 602.39(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.995 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 1.843 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2210 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0459 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1061 _reflns_number_gt 865 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0477P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1061 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0885 _refine_ls_wR_factor_gt 0.0861 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _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 0.5000 0.5000 0.0090(2) Uani 1 2 d S . . N1 N 0.1089(3) 0.3341(4) 0.3754(3) 0.0082(6) Uani 1 1 d . . . N2 N 0.0568(3) 0.1656(5) 0.3054(3) 0.0124(7) Uani 1 1 d . . . N3 N 0.1388(3) 0.1209(5) 0.2093(3) 0.0136(7) Uani 1 1 d . . . N4 N 0.2454(3) 0.2587(5) 0.2135(3) 0.0136(7) Uani 1 1 d . . . N5 N 0.4816(3) 0.7808(5) 0.4183(3) 0.0135(7) Uani 1 1 d . . . N6 N 0.3703(3) 0.8579(5) 0.4799(3) 0.0135(7) Uani 1 1 d . . . N7 N 0.1311(3) 0.7533(4) 0.4902(3) 0.0109(7) Uani 1 1 d . . . H7A H 0.1413 0.8114 0.5744 0.013 Uiso 1 1 d R . . H7B H 0.0868 0.8469 0.4332 0.013 Uiso 1 1 d R . . C1 C 0.2250(4) 0.3864(5) 0.3174(3) 0.0097(7) Uani 1 1 d . . . C2 C 0.3095(4) 0.5608(5) 0.3643(3) 0.0102(8) Uani 1 1 d . . . C3 C 0.2683(4) 0.7241(5) 0.4467(3) 0.0091(7) Uani 1 1 d . . . C4 C 0.4479(4) 0.6036(6) 0.3481(3) 0.0126(8) Uani 1 1 d . . . H4 H 0.5068 0.5252 0.2982 0.015 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 0.0084(3) 0.0084(3) 0.0111(3) -0.0017(2) 0.0059(2) -0.0020(3) N1 0.0077(14) 0.0085(15) 0.0083(14) 0.0007(11) 0.0006(11) -0.0020(13) N2 0.0109(15) 0.0116(16) 0.0151(15) -0.0020(12) 0.0032(12) -0.0016(14) N3 0.0114(15) 0.0152(17) 0.0152(15) -0.0048(12) 0.0062(12) -0.0033(14) N4 0.0103(15) 0.0163(17) 0.0147(15) -0.0035(13) 0.0042(12) -0.0020(14) N5 0.0115(15) 0.0160(17) 0.0137(15) -0.0006(12) 0.0050(12) -0.0006(14) N6 0.0123(16) 0.0118(16) 0.0169(15) -0.0011(12) 0.0042(12) -0.0030(14) N7 0.0118(15) 0.0097(15) 0.0113(14) -0.0016(11) 0.0021(12) -0.0008(14) C1 0.0083(17) 0.0105(19) 0.0103(17) 0.0019(14) 0.0014(14) 0.0026(16) C2 0.0100(18) 0.0111(18) 0.0099(16) 0.0011(13) 0.0024(14) -0.0034(16) C3 0.0091(17) 0.0097(18) 0.0092(16) 0.0032(13) 0.0049(14) -0.0023(15) C4 0.0125(18) 0.0125(19) 0.0135(18) 0.0003(15) 0.0053(14) -0.0016(17) _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 N1 1.990(3) . ? Cu1 N1 1.990(3) 3_566 ? Cu1 N7 2.070(3) 3_566 ? Cu1 N7 2.070(3) . ? Cu1 N3 2.460(3) 2 ? Cu1 N3 2.460(3) 4_566 ? N1 C1 1.343(4) . ? N1 N2 1.353(4) . ? N2 N3 1.314(4) . ? N3 N4 1.355(4) . ? N3 Cu1 2.460(3) 2_545 ? N4 C1 1.334(4) . ? N5 C4 1.355(4) . ? N5 N6 1.370(4) . ? N6 C3 1.324(4) . ? N7 C3 1.437(4) . ? N7 H7A 0.9000 . ? N7 H7B 0.9000 . ? C1 C2 1.436(5) . ? C2 C4 1.384(5) . ? C2 C3 1.404(5) . ? C4 H4 0.9300 . ? 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 Cu1 N1 180.000(1) . 3_566 ? N1 Cu1 N7 87.94(11) . 3_566 ? N1 Cu1 N7 92.06(11) 3_566 3_566 ? N1 Cu1 N7 92.06(11) . . ? N1 Cu1 N7 87.94(11) 3_566 . ? N7 Cu1 N7 180.0 3_566 . ? N1 Cu1 N3 86.46(10) . 2 ? N1 Cu1 N3 93.54(10) 3_566 2 ? N7 Cu1 N3 90.08(10) 3_566 2 ? N7 Cu1 N3 89.92(10) . 2 ? N1 Cu1 N3 93.54(10) . 4_566 ? N1 Cu1 N3 86.46(10) 3_566 4_566 ? N7 Cu1 N3 89.92(10) 3_566 4_566 ? N7 Cu1 N3 90.08(10) . 4_566 ? N3 Cu1 N3 180.00(8) 2 4_566 ? C1 N1 N2 105.8(3) . . ? C1 N1 Cu1 129.1(2) . . ? N2 N1 Cu1 123.2(2) . . ? N3 N2 N1 108.5(3) . . ? N2 N3 N4 109.8(3) . . ? N2 N3 Cu1 110.3(2) . 2_545 ? N4 N3 Cu1 125.7(2) . 2_545 ? C1 N4 N3 105.2(3) . . ? C4 N5 N6 111.6(3) . . ? C3 N6 N5 104.4(3) . . ? C3 N7 Cu1 119.5(2) . . ? C3 N7 H7A 107.5 . . ? Cu1 N7 H7A 107.5 . . ? C3 N7 H7B 107.5 . . ? Cu1 N7 H7B 107.5 . . ? H7A N7 H7B 107.0 . . ? N4 C1 N1 110.7(3) . . ? N4 C1 C2 127.2(3) . . ? N1 C1 C2 122.1(3) . . ? C4 C2 C3 104.1(3) . . ? C4 C2 C1 129.9(3) . . ? C3 C2 C1 125.9(3) . . ? N6 C3 C2 112.6(3) . . ? N6 C3 N7 121.6(3) . . ? C2 C3 N7 125.8(3) . . ? N5 C4 C2 107.3(3) . . ? N5 C4 H4 126.4 . . ? C2 C4 H4 126.4 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.863 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 920060' ####################################################################### # # 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_shelx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 Cd N14 O2.50' _chemical_formula_weight 452.69 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' Cd Cd -0.8075 1.2024 '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' H H 0.0000 0.0000 '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/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.3955(17) _cell_length_b 16.678(3) _cell_length_c 13.398(4) _cell_angle_alpha 90.00 _cell_angle_beta 128.62(2) _cell_angle_gamma 90.00 _cell_volume 1465.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.051 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 1.537 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7485 _exptl_absorpt_correction_T_max 0.9848 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8195 _diffrn_reflns_av_R_equivalents 0.0432 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2573 _reflns_number_gt 2070 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0311P)^2^+18.5130P] 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 2573 _refine_ls_number_parameters 245 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0609 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1319 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.185 _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 0.53687(9) 0.75298(4) 0.36970(5) 0.0211(2) Uani 1 1 d . . . C1 C 0.5777(11) 0.7579(5) 0.6325(7) 0.0186(17) Uani 1 1 d . . . C2 C 0.8814(14) 0.8478(6) 0.7915(9) 0.030(2) Uani 1 1 d . . . H2 H 0.9335 0.8215 0.8674 0.036 Uiso 1 1 calc R . . C3 C 0.7064(12) 0.8276(5) 0.6702(8) 0.0210(18) Uani 1 1 d . . . C4 C 0.6968(12) 0.8857(5) 0.5906(8) 0.0223(18) Uani 1 1 d . . . C5 C 0.0560(11) 0.7341(5) 0.1103(8) 0.0206(19) Uani 1 1 d . . . C6 C 0.0118(14) 0.6294(6) -0.0449(9) 0.033(2) Uani 1 1 d . . . H6 H -0.1078 0.6481 -0.1208 0.039 Uiso 1 1 calc R . . C7 C 0.1073(12) 0.6625(5) 0.0746(7) 0.0206(18) Uani 1 1 d . . . C8 C 0.2783(12) 0.6113(5) 0.1554(8) 0.0226(18) Uani 1 1 d . . . N1 N 0.4771(10) 0.7252(4) 0.5176(7) 0.0237(16) Uani 1 1 d . . . N2 N 0.3794(11) 0.6605(4) 0.5164(7) 0.0264(17) Uani 1 1 d . . . N3 N 0.4208(11) 0.6548(4) 0.6280(7) 0.0260(17) Uani 1 1 d . . . N4 N 0.5437(11) 0.7159(4) 0.7031(6) 0.0219(16) Uani 1 1 d . . . N5 N 0.9603(11) 0.9122(5) 0.7779(7) 0.0313(18) Uani 1 1 d . . . H5 H 1.0704 0.9354 0.8405 0.038 Uiso 1 1 calc R . . N6 N 0.8481(11) 0.9375(4) 0.6543(7) 0.0271(17) Uani 1 1 d . . . N7 N 0.5552(12) 0.8880(5) 0.4549(7) 0.0295(18) Uani 1 1 d . . . H7A H 0.5952 0.9244 0.4251 0.035 Uiso 1 1 calc R . . H7B H 0.4314 0.9024 0.4293 0.035 Uiso 1 1 calc R . . N8 N 0.1873(10) 0.7733(4) 0.2194(6) 0.0239(16) Uani 1 1 d . . . N9 N 0.0884(11) 0.8375(5) 0.2175(7) 0.0278(17) Uani 1 1 d . . . N10 N -0.0957(11) 0.8375(4) 0.1094(7) 0.0280(17) Uani 1 1 d . . . N11 N -0.1231(10) 0.7721(4) 0.0383(7) 0.0230(16) Uani 1 1 d . . . N12 N 0.1186(12) 0.5667(5) -0.0338(7) 0.036(2) Uani 1 1 d . . . H12 H 0.0876 0.5383 -0.0973 0.044 Uiso 1 1 calc R . . N13 N 0.2833(12) 0.5523(5) 0.0900(7) 0.0311(18) Uani 1 1 d . . . N14 N 0.4303(11) 0.6180(4) 0.2907(7) 0.0279(17) Uani 1 1 d . . . H14A H 0.5404 0.5896 0.3147 0.034 Uiso 1 1 calc R . . H14B H 0.3820 0.5955 0.3281 0.034 Uiso 1 1 calc R . . O1 O 0.2280(15) 0.9915(6) 0.1095(9) 0.072(3) Uani 1 1 d U . . O2 O 0.7128(15) 0.9787(6) 0.1073(10) 0.074(3) Uani 1 1 d U . . O3 O 0.698(5) 0.750(2) 0.361(3) 0.061(6) Uani 0.258(12) 1 d PU . 1 O3' O 0.868(5) 0.750(2) 0.366(3) 0.061(6) Uani 0.242(12) 1 d PU . 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 Cd1 0.0170(3) 0.0312(4) 0.0109(3) -0.0004(3) 0.0066(2) 0.0006(3) C1 0.016(4) 0.025(4) 0.014(4) -0.001(3) 0.009(3) 0.001(3) C2 0.029(5) 0.035(5) 0.019(5) 0.006(4) 0.012(4) -0.004(4) C3 0.020(4) 0.028(5) 0.015(4) -0.005(3) 0.011(4) -0.005(4) C4 0.019(4) 0.026(5) 0.018(4) -0.005(3) 0.010(4) -0.004(3) C5 0.012(4) 0.026(5) 0.019(4) 0.001(3) 0.007(3) 0.000(3) C6 0.025(5) 0.039(6) 0.021(5) -0.008(4) 0.007(4) 0.009(4) C7 0.020(4) 0.029(5) 0.012(4) -0.002(3) 0.010(4) 0.000(4) C8 0.020(4) 0.024(5) 0.022(5) 0.001(4) 0.012(4) 0.000(3) N1 0.018(3) 0.034(4) 0.018(4) -0.002(3) 0.011(3) -0.003(3) N2 0.028(4) 0.026(4) 0.023(4) -0.006(3) 0.015(3) -0.010(3) N3 0.028(4) 0.029(4) 0.023(4) -0.006(3) 0.017(3) -0.009(3) N4 0.027(4) 0.026(4) 0.017(4) -0.002(3) 0.015(3) -0.005(3) N5 0.028(4) 0.036(5) 0.021(4) -0.006(3) 0.011(3) -0.014(3) N6 0.031(4) 0.027(4) 0.021(4) 0.001(3) 0.015(3) -0.003(3) N7 0.033(4) 0.032(4) 0.023(4) 0.004(3) 0.017(4) -0.002(3) N8 0.017(3) 0.034(4) 0.013(4) -0.004(3) 0.005(3) 0.003(3) N9 0.020(4) 0.034(4) 0.022(4) -0.008(3) 0.009(3) 0.001(3) N10 0.020(4) 0.026(4) 0.020(4) -0.005(3) 0.004(3) -0.002(3) N11 0.019(4) 0.023(4) 0.022(4) -0.005(3) 0.010(3) -0.001(3) N12 0.035(5) 0.041(5) 0.024(4) -0.012(4) 0.014(4) 0.004(4) N13 0.037(4) 0.025(4) 0.030(4) -0.002(3) 0.020(4) 0.001(3) N14 0.024(4) 0.030(4) 0.015(4) 0.001(3) 0.005(3) 0.000(3) O1 0.071(3) 0.071(3) 0.072(3) -0.0012(10) 0.0446(18) 0.0009(10) O2 0.072(3) 0.072(3) 0.075(3) -0.0011(10) 0.0453(18) 0.0004(10) O3 0.061(6) 0.061(6) 0.061(6) 0.0000(10) 0.038(4) 0.0000(10) O3' 0.061(6) 0.061(6) 0.061(6) 0.0000(10) 0.038(4) 0.0000(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N11 2.319(7) 4_676 ? Cd1 N8 2.325(7) . ? Cd1 N4 2.327(7) 4_575 ? Cd1 N1 2.373(7) . ? Cd1 N14 2.410(7) . ? Cd1 N7 2.486(8) . ? C1 N1 1.325(10) . ? C1 N4 1.343(10) . ? C1 C3 1.447(11) . ? C2 N5 1.332(12) . ? C2 C3 1.390(12) . ? C2 H2 0.9300 . ? C3 C4 1.406(12) . ? C4 N6 1.317(11) . ? C4 N7 1.421(11) . ? C5 N8 1.330(10) . ? C5 N11 1.335(10) . ? C5 C7 1.448(11) . ? C6 N12 1.324(12) . ? C6 C7 1.382(12) . ? C6 H6 0.9300 . ? C7 C8 1.422(12) . ? C8 N13 1.335(11) . ? C8 N14 1.427(11) . ? N1 N2 1.349(10) . ? N2 N3 1.311(10) . ? N3 N4 1.349(10) . ? N4 O3 1.75(3) 4_576 ? N4 Cd1 2.327(7) 4_576 ? N5 N6 1.363(10) . ? N5 H5 0.8600 . ? N7 H7A 0.9000 . ? N7 H7B 0.9000 . ? N8 N9 1.345(10) . ? N9 N10 1.301(10) . ? N10 N11 1.371(10) . ? N11 Cd1 2.319(7) 4_475 ? N12 N13 1.363(11) . ? N12 H12 0.8600 . ? N14 H14A 0.9000 . ? N14 H14B 0.9000 . ? O3 N4 1.75(3) 4_575 ? 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 N11 Cd1 N8 172.3(3) 4_676 . ? N11 Cd1 N4 102.8(2) 4_676 4_575 ? N8 Cd1 N4 84.9(2) . 4_575 ? N11 Cd1 N1 85.7(2) 4_676 . ? N8 Cd1 N1 86.6(2) . . ? N4 Cd1 N1 171.5(2) 4_575 . ? N11 Cd1 N14 98.8(2) 4_676 . ? N8 Cd1 N14 80.4(2) . . ? N4 Cd1 N14 90.7(3) 4_575 . ? N1 Cd1 N14 88.3(3) . . ? N11 Cd1 N7 91.7(2) 4_676 . ? N8 Cd1 N7 87.0(2) . . ? N4 Cd1 N7 101.9(2) 4_575 . ? N1 Cd1 N7 77.2(2) . . ? N14 Cd1 N7 161.4(3) . . ? N1 C1 N4 110.0(7) . . ? N1 C1 C3 122.1(7) . . ? N4 C1 C3 127.9(7) . . ? N5 C2 C3 106.8(8) . . ? N5 C2 H2 126.6 . . ? C3 C2 H2 126.6 . . ? C2 C3 C4 103.8(7) . . ? C2 C3 C1 128.2(8) . . ? C4 C3 C1 127.7(7) . . ? N6 C4 C3 112.6(7) . . ? N6 C4 N7 120.7(8) . . ? C3 C4 N7 126.5(7) . . ? N8 C5 N11 110.3(7) . . ? N8 C5 C7 123.8(7) . . ? N11 C5 C7 125.9(7) . . ? N12 C6 C7 108.8(8) . . ? N12 C6 H6 125.6 . . ? C7 C6 H6 125.6 . . ? C6 C7 C8 102.8(8) . . ? C6 C7 C5 129.4(8) . . ? C8 C7 C5 127.7(7) . . ? N13 C8 C7 111.9(8) . . ? N13 C8 N14 121.5(8) . . ? C7 C8 N14 126.6(8) . . ? C1 N1 N2 106.5(7) . . ? C1 N1 Cd1 125.2(5) . . ? N2 N1 Cd1 126.1(5) . . ? N3 N2 N1 108.6(7) . . ? N2 N3 N4 109.2(7) . . ? C1 N4 N3 105.6(7) . . ? C1 N4 O3 111.0(12) . 4_576 ? N3 N4 O3 142.5(13) . 4_576 ? C1 N4 Cd1 134.6(6) . 4_576 ? N3 N4 Cd1 114.7(5) . 4_576 ? O3 N4 Cd1 37.8(11) 4_576 4_576 ? C2 N5 N6 112.9(7) . . ? C2 N5 H5 123.5 . . ? N6 N5 H5 123.5 . . ? C4 N6 N5 103.9(7) . . ? C4 N7 Cd1 109.0(5) . . ? C4 N7 H7A 109.9 . . ? Cd1 N7 H7A 109.9 . . ? C4 N7 H7B 109.9 . . ? Cd1 N7 H7B 109.9 . . ? H7A N7 H7B 108.3 . . ? C5 N8 N9 107.0(6) . . ? C5 N8 Cd1 127.7(5) . . ? N9 N8 Cd1 124.2(5) . . ? N10 N9 N8 108.1(7) . . ? N9 N10 N11 109.9(7) . . ? C5 N11 N10 104.5(7) . . ? C5 N11 Cd1 139.9(6) . 4_475 ? N10 N11 Cd1 113.0(5) . 4_475 ? C6 N12 N13 112.2(7) . . ? C6 N12 H12 123.9 . . ? N13 N12 H12 123.9 . . ? C8 N13 N12 104.2(7) . . ? C8 N14 Cd1 115.1(5) . . ? C8 N14 H14A 108.5 . . ? Cd1 N14 H14A 108.5 . . ? C8 N14 H14B 108.5 . . ? Cd1 N14 H14B 108.5 . . ? H14A N14 H14B 107.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.779 _refine_diff_density_min -2.628 _refine_diff_density_rms 0.157 _database_code_depnum_ccdc_archive 'CCDC 920061'