#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/86/4328639.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4328639
loop_
_publ_author_name
'Prankrishna Manna'
'Saikat Kumar Seth'
'Amrita Das'
'Joanna Hemming'
'Richard Prendergast'
'Madeleine Helliwell'
'Somnath Ray Choudhury'
'Antonio Frontera'
'Subrata Mukhopadhyay'
_publ_contact_author
; 
    Subrata Mukhopadhyay 
;
_publ_section_title
;
 Anion Induced Formation of Supramolecular Associations Involving Lone
 pair-π and Anion-π Interactions in Co(II) Malonate Complexes:
 Experimental Observations, Hirshfeld Surface Analyses and DFT Studies
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3557
_journal_page_last               3571
_journal_paper_doi               10.1021/ic202317f
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C6 H8 Co O10, 4(C5 H7 N2), 2(N O3)'
_chemical_formula_sum            'C26 H36 Co N10 O16'
_chemical_formula_weight         803.58
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-10-30 # Formatted by publCIF
;
_cell_angle_alpha                89.405(4)
_cell_angle_beta                 85.886(3)
_cell_angle_gamma                77.797(3)
_cell_formula_units_Z            1
_cell_length_a                   7.0790(13)
_cell_length_b                   10.7346(19)
_cell_length_c                   11.415(2)
_cell_measurement_reflns_used    823
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.63
_cell_volume                     845.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6739
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       block
_exptl_crystal_F_000             417
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0393P)²+0.3608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0792
_reflns_number_gt                3098
_reflns_number_total             3397
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic202317f_si_001_1.cif
_cod_data_source_block           m10ba
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               4328639
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Co1 Co 1.0000 0.5000 1.0000 0.01155(10) Uani 1 2 d S
O1 O 0.72478(16) 0.60827(11) 1.02760(10) 0.0153(2) Uani 1 1 d .
O2 O 0.42482(16) 0.69126(11) 0.98514(10) 0.0176(3) Uani 1 1 d .
O3 O 0.75394(17) 0.42738(11) 0.69631(10) 0.0168(3) Uani 1 1 d .
O4 O 0.91507(16) 0.42532(11) 0.85541(10) 0.0146(2) Uani 1 1 d .
O5 O 1.0972(2) 0.64631(13) 0.90139(12) 0.0218(3) Uani 1 1 d .
C1 C 0.5939(2) 0.63424(15) 0.95533(14) 0.0128(3) Uani 1 1 d .
C2 C 0.6455(2) 0.60188(16) 0.82623(15) 0.0142(3) Uani 1 1 d .
C3 C 0.7797(2) 0.47521(15) 0.79002(14) 0.0129(3) Uani 1 1 d .
N1 N 0.5808(2) 0.17388(15) 0.79161(14) 0.0187(3) Uani 1 1 d .
N2 N 0.3687(2) 0.35390(14) 0.73455(13) 0.0154(3) Uani 1 1 d .
C4 C 0.4942(2) 0.24370(16) 0.70594(15) 0.0158(3) Uani 1 1 d .
C5 C 0.5252(3) 0.20853(19) 0.58623(16) 0.0220(4) Uani 1 1 d .
C6 C 0.4363(3) 0.2889(2) 0.50461(17) 0.0272(4) Uani 1 1 d .
C7 C 0.3134(3) 0.4061(2) 0.53727(17) 0.0258(4) Uani 1 1 d .
C8 C 0.2804(3) 0.43523(17) 0.65285(16) 0.0192(4) Uani 1 1 d .
N3 N 0.0157(2) 0.19534(15) 0.62959(14) 0.0189(3) Uani 1 1 d .
N4 N 0.0703(2) 0.17150(14) 0.82633(12) 0.0153(3) Uani 1 1 d .
C9 C 0.0980(2) 0.12482(16) 0.71537(15) 0.0155(3) Uani 1 1 d .
C10 C 0.2169(3) 0.00145(17) 0.69785(16) 0.0187(4) Uani 1 1 d .
C11 C 0.2940(3) -0.06496(17) 0.79135(17) 0.0219(4) Uani 1 1 d .
C12 C 0.2592(3) -0.01326(17) 0.90537(17) 0.0212(4) Uani 1 1 d .
C13 C 0.1481(3) 0.10541(17) 0.92018(16) 0.0182(4) Uani 1 1 d .
N5 N 0.8755(2) 0.85958(13) 0.69136(12) 0.0169(3) Uani 1 1 d .
O6 O 0.8414(2) 0.92422(12) 0.60061(11) 0.0253(3) Uani 1 1 d .
O7 O 0.98774(18) 0.75177(11) 0.68434(11) 0.0220(3) Uani 1 1 d .
O8 O 0.79909(19) 0.90197(13) 0.78878(11) 0.0259(3) Uani 1 1 d .
H2 H 0.532(3) 0.6074(19) 0.7859(18) 0.021(5) Uiso 1 1 d .
H5 H 0.612(3) 0.129(2) 0.5685(19) 0.027(6) Uiso 1 1 d .
H8 H 0.201(3) 0.508(2) 0.6830(17) 0.019(5) Uiso 1 1 d .
H2N1 H 0.651(3) 0.101(2) 0.7800(18) 0.024(6) Uiso 1 1 d .
H2B H 0.707(3) 0.6658(19) 0.7960(17) 0.017(5) Uiso 1 1 d .
H2N3 H -0.059(3) 0.267(2) 0.6439(18) 0.022(5) Uiso 1 1 d .
H1N4 H 0.010(3) 0.248(2) 0.8349(18) 0.022(5) Uiso 1 1 d .
H10 H 0.234(3) -0.029(2) 0.623(2) 0.029(6) Uiso 1 1 d .
H13 H 0.116(3) 0.1495(19) 0.9928(18) 0.021(5) Uiso 1 1 d .
H1N3 H 0.042(3) 0.168(2) 0.558(2) 0.029(6) Uiso 1 1 d .
H2O5 H 1.059(3) 0.684(2) 0.844(2) 0.034(7) Uiso 1 1 d .
H12 H 0.309(3) -0.056(2) 0.9709(19) 0.023(5) Uiso 1 1 d .
H7 H 0.256(3) 0.460(2) 0.4828(19) 0.027(6) Uiso 1 1 d .
H6 H 0.460(3) 0.265(2) 0.424(2) 0.032(6) Uiso 1 1 d .
H1O5 H 1.203(4) 0.663(2) 0.920(2) 0.046(7) Uiso 1 1 d .
H1N1 H 0.577(3) 0.206(2) 0.858(2) 0.033(6) Uiso 1 1 d .
H11 H 0.371(3) -0.146(2) 0.7804(18) 0.024(5) Uiso 1 1 d .
H1N2 H 0.343(3) 0.372(2) 0.806(2) 0.029(6) Uiso 1 1 d .
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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O4 Co1 O4 180.00(3) 2_767 .
O4 Co1 O1 91.33(5) 2_767 .
O4 Co1 O1 88.67(5) . .
O4 Co1 O1 88.67(5) 2_767 2_767
O4 Co1 O1 91.33(5) . 2_767
O1 Co1 O1 180.0 . 2_767
O4 Co1 O5 87.58(5) 2_767 .
O4 Co1 O5 92.42(5) . .
O1 Co1 O5 92.41(5) . .
O1 Co1 O5 87.59(5) 2_767 .
O4 Co1 O5 92.42(5) 2_767 2_767
O4 Co1 O5 87.58(5) . 2_767
O1 Co1 O5 87.59(5) . 2_767
O1 Co1 O5 92.41(5) 2_767 2_767
O5 Co1 O5 179.999(1) . 2_767
C1 O1 Co1 128.24(10) . .
C3 O4 Co1 128.54(10) . .
Co1 O5 H2O5 132.0(17) . .
Co1 O5 H1O5 115.5(18) . .
H2O5 O5 H1O5 112(2) . .
O2 C1 O1 122.53(15) . .
O2 C1 C2 118.04(14) . .
O1 C1 C2 119.35(14) . .
C1 C2 C3 120.16(14) . .
C1 C2 H2 110.4(12) . .
C3 C2 H2 106.6(12) . .
C1 C2 H2B 105.8(12) . .
C3 C2 H2B 106.1(12) . .
H2 C2 H2B 107.1(17) . .
O3 C3 O4 123.14(15) . .
O3 C3 C2 117.39(14) . .
O4 C3 C2 119.45(14) . .
C4 N1 H2N1 122.8(14) . .
C4 N1 H1N1 119.5(16) . .
H2N1 N1 H1N1 117(2) . .
C4 N2 C8 122.94(16) . .
C4 N2 H1N2 117.8(15) . .
C8 N2 H1N2 119.2(15) . .
N1 C4 N2 118.52(16) . .
N1 C4 C5 123.66(16) . .
N2 C4 C5 117.82(16) . .
C6 C5 C4 119.28(17) . .
C6 C5 H5 124.5(13) . .
C4 C5 H5 116.2(13) . .
C5 C6 C7 121.27(18) . .
C5 C6 H6 118.9(14) . .
C7 C6 H6 119.8(14) . .
C8 C7 C6 118.19(18) . .
C8 C7 H7 120.8(14) . .
C6 C7 H7 121.0(14) . .
C7 C8 N2 120.35(17) . .
C7 C8 H8 124.9(13) . .
N2 C8 H8 114.8(13) . .
C9 N3 H2N3 120.8(14) . .
C9 N3 H1N3 118.5(15) . .
H2N3 N3 H1N3 121(2) . .
C9 N4 C13 123.29(15) . .
C9 N4 H1N4 116.5(14) . .
C13 N4 H1N4 119.9(14) . .
N3 C9 N4 119.22(16) . .
N3 C9 C10 123.58(16) . .
N4 C9 C10 117.20(15) . .
C11 C10 C9 119.64(17) . .
C11 C10 H10 123.9(14) . .
C9 C10 H10 116.5(14) . .
C10 C11 C12 121.16(17) . .
C10 C11 H11 119.9(13) . .
C12 C11 H11 118.9(13) . .
C13 C12 C11 118.40(17) . .
C13 C12 H12 118.2(13) . .
C11 C12 H12 123.4(13) . .
C12 C13 N4 120.29(17) . .
C12 C13 H13 125.4(12) . .
N4 C13 H13 114.3(12) . .
O8 N5 O6 120.17(14) . .
O8 N5 O7 119.99(14) . .
O6 N5 O7 119.84(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 O4 2.0252(11) 2_767
Co1 O4 2.0253(11) .
Co1 O1 2.0514(11) .
Co1 O1 2.0514(11) 2_767
Co1 O5 2.1253(13) .
Co1 O5 2.1253(13) 2_767
O1 C1 1.270(2) .
O2 C1 1.249(2) .
O3 C3 1.233(2) .
O4 C3 1.2803(19) .
O5 H2O5 0.80(3) .
O5 H1O5 0.85(3) .
C1 C2 1.518(2) .
C2 C3 1.527(2) .
C2 H2 0.95(2) .
C2 H2B 0.94(2) .
N1 C4 1.330(2) .
N1 H2N1 0.84(2) .
N1 H1N1 0.83(2) .
N2 C4 1.348(2) .
N2 C8 1.363(2) .
N2 H1N2 0.84(2) .
C4 C5 1.411(2) .
C5 C6 1.359(3) .
C5 H5 0.95(2) .
C6 C7 1.407(3) .
C6 H6 0.96(2) .
C7 C8 1.351(3) .
C7 H7 0.90(2) .
C8 H8 0.92(2) .
N3 C9 1.323(2) .
N3 H2N3 0.84(2) .
N3 H1N3 0.86(2) .
N4 C9 1.353(2) .
N4 C13 1.363(2) .
N4 H1N4 0.85(2) .
C9 C10 1.418(2) .
C10 C11 1.360(3) .
C10 H10 0.91(2) .
C11 C12 1.405(3) .
C11 H11 0.93(2) .
C12 C13 1.353(3) .
C12 H12 0.92(2) .
C13 H13 0.95(2) .
N5 O8 1.2477(19) .
N5 O6 1.2501(19) .
N5 O7 1.2574(18) .
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
O5 H1O5 O2 0.85(3) 1.87(3) 2.7065(18) 171(3) 1_655
N4 H1N4 O4 0.85(2) 1.89(2) 2.7280(19) 171(2) 1_455
N1 H1N1 O2 0.83(2) 2.11(3) 2.938(2) 172(2) 2_667
N3 H2N3 O3 0.84(2) 2.01(2) 2.847(2) 173(2) 1_455
N2 H1N2 O1 0.84(2) 1.92(2) 2.7614(19) 173(2) 2_667
O5 H2O5 O7 0.80(3) 2.01(3) 2.8048(19) 170(2) .
N3 H1N3 O6 0.86(2) 2.10(2) 2.952(2) 168(2) 2_666
N1 H2N1 O8 0.84(2) 2.17(2) 2.999(2) 167(2) 1_545
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
O4 Co1 O1 C1 162.60(13) 2_767
O4 Co1 O1 C1 -17.40(13) .
O1 Co1 O1 C1 -103(28) 2_767
O5 Co1 O1 C1 74.97(14) .
O5 Co1 O1 C1 -105.04(14) 2_767
O4 Co1 O4 C3 117(64) 2_767
O1 Co1 O4 C3 26.67(13) .
O1 Co1 O4 C3 -153.33(13) 2_767
O5 Co1 O4 C3 -65.69(14) .
O5 Co1 O4 C3 114.31(14) 2_767
Co1 O1 C1 O2 172.94(11) .
Co1 O1 C1 C2 -10.6(2) .
O2 C1 C2 C3 -141.68(15) .
O1 C1 C2 C3 41.7(2) .
Co1 O4 C3 O3 171.60(11) .
Co1 O4 C3 C2 -6.6(2) .
C1 C2 C3 O3 149.00(15) .
C1 C2 C3 O4 -32.7(2) .
C8 N2 C4 N1 176.50(16) .
C8 N2 C4 C5 -4.0(2) .
N1 C4 C5 C6 -177.22(18) .
N2 C4 C5 C6 3.3(3) .
C4 C5 C6 C7 -0.3(3) .
C5 C6 C7 C8 -2.2(3) .
C6 C7 C8 N2 1.7(3) .
C4 N2 C8 C7 1.5(3) .
C13 N4 C9 N3 179.53(16) .
C13 N4 C9 C10 -0.9(2) .
N3 C9 C10 C11 -179.29(17) .
N4 C9 C10 C11 1.2(3) .
C9 C10 C11 C12 -0.4(3) .
C10 C11 C12 C13 -0.7(3) .
C11 C12 C13 N4 1.0(3) .
C9 N4 C13 C12 -0.2(3) .
