# 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_1 #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C H Co N Na O' _chemical_formula_weight 124.95 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' Na Na 0.0362 0.0249 '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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 24.377(3) _cell_length_b 24.377(3) _cell_length_c 24.856(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 12792(4) _cell_formula_units_Z 120 _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 1.946 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 7200 _exptl_absorpt_coefficient_mu 3.931 _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 39154 _diffrn_reflns_av_R_equivalents 0.0795 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.87 _reflns_number_total 6791 _reflns_number_gt 4986 _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^)+(0.2000P)^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 6791 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2073 _refine_ls_R_factor_gt 0.1868 _refine_ls_wR_factor_ref 0.5476 _refine_ls_wR_factor_gt 0.5340 _refine_ls_goodness_of_fit_ref 2.188 _refine_ls_restrained_S_all 2.188 _refine_ls_shift/su_max 0.054 _refine_ls_shift/su_mean 0.014 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 C5 C 0.5836(4) 0.6755(5) 0.2703(4) 0.042(2) Uani 1 1 d . . . O5 O 0.5483(3) 0.6190(4) 0.2827(3) 0.0423(17) Uani 1 1 d . . . N5 N 0.5111(3) 0.6503(4) 0.1979(3) 0.0384(19) Uani 1 1 d . . . C6 C 0.5663(4) 0.6960(4) 0.2203(4) 0.036(2) Uani 1 1 d . . . Co1 Co 0.56633(6) 0.80188(5) 0.09496(4) 0.0294(5) Uani 1 1 d . . . Co2 Co 0.3333 0.6667 -0.04811(8) 0.0277(6) Uani 1 3 d S . . O1 O 0.6103(3) 0.7705(3) 0.0457(3) 0.0349(14) Uani 1 1 d . . . O3 O 0.3818(4) 0.6363(3) -0.0932(2) 0.0392(15) Uani 1 1 d . . . O8 O 0.6422(3) 0.8440(3) 0.1428(3) 0.0398(16) Uani 1 1 d . . . N4 N 0.5453(4) 0.7317(4) 0.1470(4) 0.044(2) Uani 1 1 d . . . N3 N 0.4160(4) 0.7063(3) -0.0084(3) 0.0335(17) Uani 1 1 d . . . N1 N 0.4974(4) 0.7533(4) 0.0418(3) 0.0337(17) Uani 1 1 d . . . O1W O 0.3792(4) 0.6322(4) 0.1186(3) 0.057(2) Uani 1 1 d . . . H1W H 0.3539 0.6064 0.0971 0.085 Uiso 1 1 calc R . . C1 C 0.4582(4) 0.6930(4) -0.0291(3) 0.0320(19) Uani 1 1 d . . . N2 N 0.4378(4) 0.7426(4) 0.0338(3) 0.0401(19) Uani 1 1 d . . . C8 C 0.5884(4) 0.7483(4) 0.1876(4) 0.035(2) Uani 1 1 d . . . C2 C 0.5118(4) 0.7240(4) 0.0037(3) 0.0328(19) Uani 1 1 d . . . C3 C 0.4371(6) 0.6521(5) -0.0774(4) 0.047(3) Uani 1 1 d . . . O2 O 0.5963(4) 0.7086(4) -0.0247(3) 0.057(2) Uani 1 1 d . . . O4 O 0.4726(5) 0.6355(5) -0.1011(3) 0.067(3) Uani 1 1 d . . . O6 O 0.6320(4) 0.7127(5) 0.2966(4) 0.088(4) Uani 1 1 d . . . C4 C 0.5765(5) 0.7326(5) 0.0076(4) 0.036(2) Uani 1 1 d . . . O7 O 0.6837(5) 0.8350(4) 0.2217(5) 0.090(4) Uani 1 1 d . . . C7 C 0.6432(5) 0.8149(5) 0.1841(5) 0.048(3) Uani 1 1 d . . . Na1 Na 0.5450(2) 0.6098(2) -0.06651(16) 0.0502(12) Uani 1 1 d . . . N6 N 0.4992(3) 0.6732(4) 0.1526(4) 0.041(2) Uani 1 1 d . . . O3W O 0.4807(6) 0.5588(5) 0.0078(4) 0.092(4) Uani 1 1 d . . . O2W O 0.6111(6) 0.6646(6) -0.1419(4) 0.087(3) Uani 1 1 d . . . Co3 Co 0.3333 0.6667 0.1667 0.0472(9) Uani 1 6 d S . . 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 C5 0.025(4) 0.052(6) 0.039(5) -0.018(4) -0.012(4) 0.013(4) O5 0.028(3) 0.063(5) 0.038(4) -0.012(3) -0.014(3) 0.023(3) N5 0.022(3) 0.045(4) 0.047(5) -0.022(4) -0.008(3) 0.016(3) C6 0.023(4) 0.040(5) 0.045(5) -0.011(4) -0.004(4) 0.016(4) Co1 0.0365(8) 0.0261(7) 0.0306(8) -0.0046(4) -0.0071(4) 0.0192(5) Co2 0.0255(7) 0.0255(7) 0.0321(11) 0.000 0.000 0.0128(4) O1 0.035(3) 0.037(3) 0.038(3) 0.001(3) 0.004(3) 0.022(3) O3 0.053(4) 0.043(4) 0.028(3) -0.007(3) 0.004(3) 0.029(3) O8 0.024(3) 0.035(3) 0.059(4) -0.015(3) -0.006(3) 0.014(3) N4 0.034(4) 0.060(5) 0.051(5) -0.028(4) -0.024(4) 0.033(4) N3 0.038(4) 0.032(4) 0.040(4) 0.013(3) 0.015(3) 0.024(3) N1 0.049(4) 0.033(4) 0.029(4) 0.006(3) 0.015(3) 0.027(4) O1W 0.060(5) 0.070(6) 0.050(5) -0.011(4) -0.002(4) 0.040(4) C1 0.036(4) 0.038(4) 0.028(4) 0.005(3) 0.016(3) 0.023(4) N2 0.055(5) 0.039(4) 0.035(4) 0.010(3) 0.021(4) 0.030(4) C8 0.024(4) 0.037(5) 0.048(5) -0.014(4) -0.013(4) 0.019(4) C2 0.043(5) 0.039(5) 0.024(4) 0.001(3) 0.007(3) 0.027(4) C3 0.066(7) 0.057(6) 0.039(5) 0.000(4) 0.013(5) 0.047(6) O2 0.075(5) 0.064(5) 0.056(5) -0.015(4) 0.008(4) 0.052(5) O4 0.102(7) 0.103(7) 0.046(4) -0.001(4) 0.014(4) 0.089(6) O6 0.048(5) 0.091(7) 0.066(6) 0.005(5) -0.036(4) -0.010(5) C4 0.047(5) 0.044(5) 0.029(4) 0.006(4) 0.010(4) 0.031(4) O7 0.079(6) 0.054(5) 0.133(10) -0.047(6) -0.085(7) 0.030(5) C7 0.036(5) 0.038(5) 0.076(8) -0.023(5) -0.026(5) 0.023(4) Na1 0.062(3) 0.062(3) 0.048(2) -0.006(2) 0.015(2) 0.046(2) N6 0.022(3) 0.050(5) 0.054(5) -0.020(4) -0.009(3) 0.020(4) O3W 0.139(10) 0.088(7) 0.078(7) 0.030(6) 0.050(7) 0.080(8) O2W 0.111(9) 0.098(8) 0.068(7) 0.020(6) 0.039(6) 0.063(7) Co3 0.0461(13) 0.0461(13) 0.049(2) 0.000 0.000 0.0230(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 C5 O6 1.254(12) . ? C5 O5 1.244(13) . ? C5 C6 1.478(15) . ? O5 Co1 2.027(6) 14_455 ? N5 N6 1.351(12) . ? N5 C6 1.364(11) . ? N5 Co1 1.993(9) 14_455 ? C6 C8 1.375(14) . ? Co1 N5 1.993(9) 15 ? Co1 N1 1.995(8) . ? Co1 O8 1.997(7) . ? Co1 N4 1.997(10) . ? Co1 O1 2.013(6) . ? Co1 O5 2.027(6) 15 ? Co2 N3 2.005(8) 2_665 ? Co2 N3 2.005(8) . ? Co2 N3 2.005(8) 3_565 ? Co2 O3 2.018(6) 2_665 ? Co2 O3 2.018(6) 3_565 ? Co2 O3 2.018(6) . ? O1 C4 1.293(12) . ? O3 C3 1.265(14) . ? O8 C7 1.256(14) . ? N4 N6 1.309(12) . ? N4 C8 1.364(11) . ? N3 N2 1.302(12) . ? N3 C1 1.327(11) . ? N1 C2 1.334(11) . ? N1 N2 1.358(12) . ? O1W Co3 2.080(8) . ? C1 C2 1.399(13) . ? C1 C3 1.479(14) . ? C8 C7 1.503(14) . ? C2 C4 1.488(13) . ? C3 O4 1.270(12) . ? O2 C4 1.224(11) . ? O2 Na1 2.330(9) . ? O4 Na1 2.313(9) . ? O6 Na1 2.314(10) 6_565 ? O7 C7 1.265(13) . ? O7 Na1 2.290(10) 6_565 ? Na1 O7 2.290(10) 8_654 ? Na1 O6 2.314(10) 8_654 ? Na1 O3W 2.338(11) . ? Na1 O2W 2.397(11) . ? Co3 O1W 2.080(8) 14_455 ? Co3 O1W 2.080(8) 15 ? Co3 O1W 2.080(8) 3_565 ? Co3 O1W 2.080(8) 2_665 ? Co3 O1W 2.080(8) 13_565 ? 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 O6 C5 O5 123.6(11) . . ? O6 C5 C6 121.1(10) . . ? O5 C5 C6 115.3(8) . . ? C5 O5 Co1 117.2(6) . 14_455 ? N6 N5 C6 109.4(8) . . ? N6 N5 Co1 136.0(6) . 14_455 ? C6 N5 Co1 114.6(7) . 14_455 ? N5 C6 C8 106.5(8) . . ? N5 C6 C5 113.5(9) . . ? C8 C6 C5 140.0(8) . . ? N5 Co1 N1 99.5(3) 15 . ? N5 Co1 O8 89.5(3) 15 . ? N1 Co1 O8 171.0(3) . . ? N5 Co1 N4 97.7(3) 15 . ? N1 Co1 N4 98.1(3) . . ? O8 Co1 N4 80.2(3) . . ? N5 Co1 O1 170.8(3) 15 . ? N1 Co1 O1 79.7(3) . . ? O8 Co1 O1 91.4(3) . . ? N4 Co1 O1 91.5(3) . . ? N5 Co1 O5 79.0(3) 15 15 ? N1 Co1 O5 90.0(3) . 15 ? O8 Co1 O5 92.1(3) . 15 ? N4 Co1 O5 171.7(3) . 15 ? O1 Co1 O5 91.8(3) . 15 ? N3 Co2 N3 97.8(3) 2_665 . ? N3 Co2 N3 97.8(3) 2_665 3_565 ? N3 Co2 N3 97.8(3) . 3_565 ? N3 Co2 O3 79.6(3) 2_665 2_665 ? N3 Co2 O3 90.8(3) . 2_665 ? N3 Co2 O3 171.3(3) 3_565 2_665 ? N3 Co2 O3 90.8(3) 2_665 3_565 ? N3 Co2 O3 171.3(3) . 3_565 ? N3 Co2 O3 79.6(3) 3_565 3_565 ? O3 Co2 O3 92.2(3) 2_665 3_565 ? N3 Co2 O3 171.3(3) 2_665 . ? N3 Co2 O3 79.6(3) . . ? N3 Co2 O3 90.8(3) 3_565 . ? O3 Co2 O3 92.2(3) 2_665 . ? O3 Co2 O3 92.2(3) 3_565 . ? C4 O1 Co1 116.7(6) . . ? C3 O3 Co2 116.5(6) . . ? C7 O8 Co1 118.1(6) . . ? N6 N4 C8 111.1(9) . . ? N6 N4 Co1 135.6(6) . . ? C8 N4 Co1 113.3(7) . . ? N2 N3 C1 112.0(8) . . ? N2 N3 Co2 134.0(6) . . ? C1 N3 Co2 114.0(6) . . ? C2 N1 N2 109.6(8) . . ? C2 N1 Co1 114.8(6) . . ? N2 N1 Co1 135.6(6) . . ? N3 C1 C2 105.7(8) . . ? N3 C1 C3 115.4(8) . . ? C2 C1 C3 138.9(8) . . ? N3 N2 N1 106.5(7) . . ? N4 C8 C6 106.0(8) . . ? N4 C8 C7 114.5(9) . . ? C6 C8 C7 139.5(9) . . ? N1 C2 C1 106.2(8) . . ? N1 C2 C4 115.0(8) . . ? C1 C2 C4 138.8(8) . . ? O4 C3 O3 123.5(10) . . ? O4 C3 C1 121.9(11) . . ? O3 C3 C1 114.5(8) . . ? C4 O2 Na1 130.5(8) . . ? C3 O4 Na1 130.4(8) . . ? C5 O6 Na1 130.0(9) . 6_565 ? O2 C4 O1 124.1(9) . . ? O2 C4 C2 122.3(9) . . ? O1 C4 C2 113.5(7) . . ? C7 O7 Na1 131.3(7) . 6_565 ? O8 C7 O7 128.0(11) . . ? O8 C7 C8 113.6(8) . . ? O7 C7 C8 118.4(11) . . ? O7 Na1 O4 91.6(4) 8_654 . ? O7 Na1 O2 176.8(4) 8_654 . ? O4 Na1 O2 88.5(4) . . ? O7 Na1 O6 87.8(4) 8_654 8_654 ? O4 Na1 O6 176.6(4) . 8_654 ? O2 Na1 O6 91.9(4) . 8_654 ? O7 Na1 O3W 89.4(4) 8_654 . ? O4 Na1 O3W 92.2(4) . . ? O2 Na1 O3W 93.9(4) . . ? O6 Na1 O3W 91.2(4) 8_654 . ? O7 Na1 O2W 92.0(4) 8_654 . ? O4 Na1 O2W 87.1(4) . . ? O2 Na1 O2W 84.8(4) . . ? O6 Na1 O2W 89.5(5) 8_654 . ? O3W Na1 O2W 178.5(4) . . ? N4 N6 N5 107.0(7) . . ? O1W Co3 O1W 90.3(3) 14_455 15 ? O1W Co3 O1W 89.7(3) 14_455 3_565 ? O1W Co3 O1W 179.997(1) 15 3_565 ? O1W Co3 O1W 179.997(1) 14_455 2_665 ? O1W Co3 O1W 89.7(3) 15 2_665 ? O1W Co3 O1W 90.3(3) 3_565 2_665 ? O1W Co3 O1W 89.7(3) 14_455 . ? O1W Co3 O1W 89.7(3) 15 . ? O1W Co3 O1W 90.3(3) 3_565 . ? O1W Co3 O1W 90.3(3) 2_665 . ? O1W Co3 O1W 90.3(3) 14_455 13_565 ? O1W Co3 O1W 90.3(3) 15 13_565 ? O1W Co3 O1W 89.7(3) 3_565 13_565 ? O1W Co3 O1W 89.7(3) 2_665 13_565 ? O1W Co3 O1W 180.0(4) . 13_565 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 4.466 _refine_diff_density_min -2.003 _refine_diff_density_rms 0.351 _database_code_depnum_ccdc_archive 'CCDC 917264'