# 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_IFP-5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-methyl-imidazolate-4-amide-5-imidato)-cobalt(II) dimethylformamide solvate ; _chemical_formula_moiety 'C6 H6 Co N4 O2, 0.5(C3 H7 N O) ' _chemical_formula_sum 'C7.50 H9.50 Co N4.50 O2.50' _chemical_formula_weight 261.63 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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 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 17.7780(13) _cell_length_b 17.7780(13) _cell_length_c 18.6529(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5105.6(6) _cell_formula_units_Z 18 _cell_measurement_temperature 210(2) _cell_measurement_reflns_used 10025 _cell_measurement_theta_min 1.72 _cell_measurement_theta_max 26.97 _exptl_crystal_description prism _exptl_crystal_colour violet _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2394 _exptl_absorpt_coefficient_mu 1.506 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.7279 _exptl_absorpt_correction_T_max 0.8078 _exptl_absorpt_process_details 'X-Red (Stoe, 2004)' _exptl_special_details ; The crystal was embedded in perfluoropolyalkylether oil. ; _diffrn_ambient_temperature 210(2) _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_monochromator 'plane graphite' _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_type STOE _diffrn_detector_area_resol_mean 6.67 _diffrn_measurement_method '\w scan, \d \w = 1.0 deg' _diffrn_measurement_details ; 180 frames, 5 min exposure time ; _diffrn_reflns_number 11007 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2002 _reflns_number_gt 1304 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-AREA (Stoe, 2004)' _computing_cell_refinement 'X-AREA (Stoe, 2004)' _computing_data_reduction 'X-RED (Stoe, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0715P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2002 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_special_details ; The unit cell contains channels filled with disordered solvent molecules. In spite of several attempts, no chemically reasonable solution could be received for the solvent species in the channels of the crystal material. Very high displacement parameters, high esdimates and partial occupany due to the disorder make it impossible to determine accurate atomic positions for that molecules. PLATON/SQUEEZE calculated a solvent-accessible void volume in the unit cell of 2085.2 \%A^3^ (40.8 % of the total cell volume), corresponding to 362 electrons (residual electron density after the last refinement cycle) per cell. This number agrees with about 0.5 molecules of DMF (0.5x40x18=360) per asymmetric unit. The contributions of the disordered solvent species was subtracted from the structure factor calculations, but included in D(calc), F000 & Mol.Wght. The deposited atom data (cif) reflect only known cell content. ; 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 0.61806(4) -0.04069(4) 0.20922(2) 0.0602(3) Uani 1 1 d . . . . . O1 O 0.7344(2) 0.0748(2) 0.20491(13) 0.0731(10) Uani 1 1 d . . . . . O2 O 0.5155(2) -0.0411(2) 0.25205(13) 0.0733(10) Uani 1 1 d . . . . . N1 N 0.6076(2) -0.0313(2) 0.09670(15) 0.0585(10) Uani 1 1 d . . . . . N2 N 0.6638(3) -0.0345(3) 0.31390(15) 0.0588(9) Uani 1 1 d . . . . . N3 N 0.8472(3) 0.1756(3) 0.26940(19) 0.0845(15) Uani 1 1 d . . . . . H3A H 0.875(4) 0.189(4) 0.312(3) 0.101 Uiso 1 1 d . U . . . H3B H 0.881(4) 0.215(4) 0.235(4) 0.101 Uiso 1 1 d . U . . . N4 N 0.6083(3) -0.1520(3) 0.17860(16) 0.0685(12) Uani 1 1 d . . . . . H4 H 0.604(3) -0.191(3) 0.203(3) 0.082 Uiso 1 1 d . U . . . C1 C 0.6412(3) -0.0751(3) 0.37681(18) 0.0617(12) Uani 1 1 d . . . . . C2 C 0.7755(4) 0.1009(4) 0.26358(19) 0.0680(13) Uani 1 1 d . . . . . C3 C 0.7379(3) 0.0430(3) 0.32613(19) 0.0590(11) Uani 1 1 d . . . . . C4 C 0.6209(3) -0.0932(3) 0.06467(18) 0.0587(11) Uani 1 1 d . . . . . C5 C 0.6179(3) -0.1623(3) 0.1105(2) 0.0652(12) Uani 1 1 d . . . . . C6 C 0.5635(3) -0.1635(3) 0.3875(2) 0.0785(15) Uani 1 1 d . . . . . H6A H 0.5174 -0.1703 0.3565 0.118 Uiso 1 1 calc R U . . . H6B H 0.5448 -0.1699 0.4365 0.118 Uiso 1 1 calc R U . . . H6C H 0.5786 -0.2070 0.3762 0.118 Uiso 1 1 calc R U . . . 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 0.0803(5) 0.0865(5) 0.0160(3) -0.0005(2) 0.0010(2) 0.0433(4) O1 0.095(2) 0.089(2) 0.0182(13) 0.0042(12) -0.0056(13) 0.0331(19) O2 0.089(2) 0.123(3) 0.0194(12) -0.0073(14) -0.0049(14) 0.061(2) N1 0.081(3) 0.081(2) 0.0188(14) -0.0016(15) -0.0020(14) 0.044(2) N2 0.077(2) 0.078(3) 0.0167(14) -0.0014(14) 0.0001(15) 0.035(2) N3 0.102(4) 0.094(3) 0.0204(16) 0.0118(18) -0.0057(18) 0.021(3) N4 0.111(3) 0.085(3) 0.0171(15) 0.0068(15) 0.0040(16) 0.055(3) C1 0.084(3) 0.081(3) 0.0206(18) -0.0015(18) -0.0041(18) 0.041(3) C2 0.090(4) 0.087(4) 0.0199(19) 0.0047(19) 0.003(2) 0.039(3) C3 0.079(3) 0.081(3) 0.0209(17) 0.0049(19) 0.0029(18) 0.043(3) C4 0.079(3) 0.074(3) 0.0216(17) -0.0009(18) 0.0019(17) 0.037(2) C5 0.095(4) 0.085(3) 0.0210(17) 0.0027(19) 0.0046(19) 0.049(3) C6 0.096(4) 0.084(4) 0.034(2) 0.001(2) -0.007(2) 0.030(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 Co1 N4 1.982(4) . ? Co1 O2 1.988(3) . ? Co1 O1 2.062(3) . ? Co1 N2 2.097(3) . ? Co1 N1 2.121(3) . ? O1 C2 1.268(5) . ? O2 C5 1.279(5) 15_445 ? N1 C1 1.365(5) 9_654 ? N1 C4 1.374(6) . ? N2 C1 1.330(5) . ? N2 C3 1.368(6) . ? N3 C2 1.307(7) . ? N3 H3A 0.91(6) . ? N3 H3B 0.91(6) . ? N4 C5 1.307(5) . ? N4 H4 0.81(5) . ? C1 N1 1.365(5) 5_545 ? C1 C6 1.500(7) . ? C2 C3 1.476(6) . ? C3 C4 1.388(5) 5_545 ? C4 C3 1.388(5) 9_654 ? C4 C5 1.474(6) . ? C5 O2 1.279(5) 14 ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? 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 N4 Co1 O2 119.36(17) . . ? N4 Co1 O1 121.78(16) . . ? O2 Co1 O1 118.70(15) . . ? N4 Co1 N2 99.12(14) . . ? O2 Co1 N2 87.54(13) . . ? O1 Co1 N2 79.32(13) . . ? N4 Co1 N1 79.98(13) . . ? O2 Co1 N1 106.34(13) . . ? O1 Co1 N1 88.11(12) . . ? N2 Co1 N1 164.67(15) . . ? C2 O1 Co1 116.0(3) . . ? C5 O2 Co1 130.8(2) 15_445 . ? C1 N1 C4 105.6(3) 9_654 . ? C1 N1 Co1 142.6(3) 9_654 . ? C4 N1 Co1 108.1(2) . . ? C1 N2 C3 106.0(3) . . ? C1 N2 Co1 142.1(3) . . ? C3 N2 Co1 111.1(2) . . ? C2 N3 H3A 118(4) . . ? C2 N3 H3B 131(4) . . ? H3A N3 H3B 110(5) . . ? C5 N4 Co1 117.9(3) . . ? C5 N4 H4 112(4) . . ? Co1 N4 H4 129(4) . . ? N2 C1 N1 112.2(4) . 5_545 ? N2 C1 C6 123.7(4) . . ? N1 C1 C6 124.0(3) 5_545 . ? O1 C2 N3 122.3(4) . . ? O1 C2 C3 116.8(5) . . ? N3 C2 C3 121.0(4) . . ? N2 C3 C4 108.7(4) . 5_545 ? N2 C3 C2 116.3(4) . . ? C4 C3 C2 135.0(5) 5_545 . ? N1 C4 C3 107.4(4) . 9_654 ? N1 C4 C5 117.8(3) . . ? C3 C4 C5 134.8(4) 9_654 . ? O2 C5 N4 127.5(4) 14 . ? O2 C5 C4 118.9(3) 14 . ? N4 C5 C4 113.5(4) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 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 C3 N2 C1 N1 -0.6(5) . . . 5_545 ? Co1 N2 C1 N1 -169.6(4) . . . 5_545 ? C3 N2 C1 C6 -179.3(5) . . . . ? Co1 N2 C1 C6 11.7(8) . . . . ? Co1 O1 C2 N3 -175.5(4) . . . . ? Co1 O1 C2 C3 3.6(6) . . . . ? C1 N2 C3 C4 0.8(5) . . . 5_545 ? Co1 N2 C3 C4 173.5(3) . . . 5_545 ? C1 N2 C3 C2 -179.4(4) . . . . ? Co1 N2 C3 C2 -6.6(5) . . . . ? O1 C2 C3 N2 2.2(6) . . . . ? N3 C2 C3 N2 -178.6(5) . . . . ? O1 C2 C3 C4 -177.9(5) . . . 5_545 ? N3 C2 C3 C4 1.2(9) . . . 5_545 ? C1 N1 C4 C3 0.2(5) 9_654 . . 9_654 ? Co1 N1 C4 C3 -163.4(3) . . . 9_654 ? C1 N1 C4 C5 177.8(4) 9_654 . . . ? Co1 N1 C4 C5 14.2(5) . . . . ? Co1 N4 C5 O2 169.9(4) . . . 14 ? Co1 N4 C5 C4 -9.3(6) . . . . ? N1 C4 C5 O2 176.3(4) . . . 14 ? C3 C4 C5 O2 -7.0(9) 9_654 . . 14 ? N1 C4 C5 N4 -4.4(6) . . . . ? C3 C4 C5 N4 172.2(5) 9_654 . . . ? 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 N3 H3A O2 0.91(6) 1.94(6) 2.800(4) 157(5) 18_545 N3 H3B O1 0.91(6) 2.17(7) 3.024(5) 156(5) 13_655 N4 H4 N1 0.81(5) 2.44(5) 3.189(5) 156(5) 14 _refine_diff_density_max 0.766 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.062 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.000 -0.002 693 120 ' ' 2 0.333 0.667 0.681 694 121 ' ' 3 0.667 0.333 0.347 694 121 ' ' # === END _database_code_depnum_ccdc_archive 'CCDC 942281'