#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/69/2016917.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2016917
loop_
_publ_author_name
'Koner, Rajesh'
'Goldberg, Israel'
_publ_section_title
;
 Probing the supramolecular interaction synthons of
 1-benzofuran-2,3-dicarboxylic acid in its monoanionic form
;
_journal_coeditor_code           FG3067
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m37
_journal_page_last               m41
_journal_paper_doi               10.1107/S0108270108040419
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C10 H5 O5)2 (C3 H4 N2)4]'
_chemical_formula_moiety         'C32 H26 Cu N8 O10'
_chemical_formula_sum            'C32 H26 Cu N8 O10'
_chemical_formula_weight         746.15
_chemical_name_systematic
;
Bis(3-carboxy-1-benzofuran-2-carboxylato-\kO³)tetrakis(1H-imidazole-
\kN³)copper(II)
;
_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           SHELXL97
_cell_angle_alpha                107.5049(12)
_cell_angle_beta                 108.4826(14)
_cell_angle_gamma                99.4472(9)
_cell_formula_units_Z            1
_cell_length_a                   8.1383(2)
_cell_length_b                   9.9782(3)
_cell_length_c                   11.3225(2)
_cell_measurement_reflns_used    2893
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      3.01
_cell_volume                     796.68(4)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1 deg. φ and ω 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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8773
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         3.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_max  0.8329
_exptl_absorpt_correction_T_min  0.7264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             383
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.619
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0367
_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)+(0.0470P)²+0.6699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                3386
_reflns_number_total             3753
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3067.cif
_cod_data_source_block           II
_cod_database_code               2016917
_cod_database_fobs_code          2016917
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.0000 0.0000 0.0000 0.01492(10) Uani d S 1 . .
N N2 -0.1003(2) 0.14435(16) 0.10111(14) 0.0161(3) Uani d . 1 . .
C C3 -0.0127(2) 0.26220(19) 0.21309(17) 0.0176(3) Uani d . 1 . .
H H3 0.1132 0.2892 0.2654 0.021 Uiso calc R 1 . .
N N4 -0.1246(2) 0.33810(17) 0.24289(15) 0.0190(3) Uani d . 1 . .
H H4 -0.0950 0.4194 0.3131 0.023 Uiso calc R 1 . .
C C5 -0.2946(3) 0.2662(2) 0.14391(18) 0.0208(4) Uani d . 1 . .
H H5 -0.4019 0.2948 0.1376 0.025 Uiso calc R 1 . .
C C6 -0.2783(2) 0.1463(2) 0.05704(18) 0.0194(4) Uani d . 1 . .
H H6 -0.3742 0.0751 -0.0215 0.023 Uiso calc R 1 . .
N N7 0.1092(2) 0.15281(16) -0.05753(14) 0.0163(3) Uani d . 1 . .
C C8 0.2159(3) 0.2953(2) 0.01880(18) 0.0213(4) Uani d . 1 . .
H H8 0.2724 0.3365 0.1142 0.026 Uiso calc R 1 . .
C C9 0.2272(3) 0.3676(2) -0.06459(19) 0.0257(4) Uani d . 1 . .
H H9 0.2913 0.4670 -0.0390 0.031 Uiso calc R 1 . .
N N10 0.1270(2) 0.26745(18) -0.19280(16) 0.0219(3) Uani d . 1 . .
H H10 0.1103 0.2836 -0.2674 0.026 Uiso calc R 1 . .
C C11 0.0593(3) 0.1408(2) -0.18408(18) 0.0200(4) Uani d . 1 . .
H H11 -0.0150 0.0535 -0.2592 0.024 Uiso calc R 1 . .
O O12 0.27000(17) 0.07457(14) 0.20648(12) 0.0204(3) Uani d . 1 . .
C C13 0.4126(2) 0.16088(19) 0.29453(16) 0.0155(3) Uani d . 1 . .
O O14 0.44501(17) 0.30256(14) 0.32920(12) 0.0181(3) Uani d . 1 . .
H H14 0.5612 0.3544 0.3987 0.022 Uiso d R 1 . .
C C15 0.5536(2) 0.10199(18) 0.36470(16) 0.0140(3) Uani d . 1 . .
C C16 0.5292(2) -0.05151(18) 0.34538(16) 0.0151(3) Uani d . 1 . .
C C17 0.3887(2) -0.1824(2) 0.26711(17) 0.0187(3) Uani d . 1 . .
H H17 0.2769 -0.1834 0.2058 0.022 Uiso calc R 1 . .
C C18 0.4188(3) -0.3100(2) 0.28246(19) 0.0223(4) Uani d . 1 . .
H H18 0.3250 -0.3996 0.2311 0.027 Uiso calc R 1 . .
C C19 0.5835(3) -0.3109(2) 0.37144(19) 0.0217(4) Uani d . 1 . .
H H19 0.5987 -0.4008 0.3789 0.026 Uiso calc R 1 . .
C C20 0.7249(3) -0.1830(2) 0.44888(18) 0.0187(3) Uani d . 1 . .
H H20 0.8373 -0.1822 0.5094 0.022 Uiso calc R 1 . .
C C21 0.6917(2) -0.05642(18) 0.43239(16) 0.0152(3) Uani d . 1 . .
O O22 0.81303(16) 0.08149(13) 0.50042(12) 0.0156(2) Uani d . 1 . .
C C23 0.7251(2) 0.17508(18) 0.45845(16) 0.0142(3) Uani d . 1 . .
C C24 0.8332(2) 0.33294(19) 0.52317(16) 0.0148(3) Uani d . 1 . .
O O25 0.99497(17) 0.36447(14) 0.59757(12) 0.0177(3) Uani d . 1 . .
O O26 0.75168(17) 0.42565(13) 0.49777(13) 0.0185(3) Uani d . 1 . .
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'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 Cu1 N2 2 . 180.00(6) ?
N2 Cu1 N7 2 . 89.79(6) ?
N2 Cu1 N7 . . 90.21(6) ?
N2 Cu1 N7 2 2 90.21(6) ?
N2 Cu1 N7 . 2 89.79(6) ?
N7 Cu1 N7 . 2 180.0 ?
C3 N2 C6 . . 105.90(15) ?
C3 N2 Cu1 . . 128.81(13) ?
C6 N2 Cu1 . . 125.00(12) ?
N2 C3 N4 . . 111.14(16) ?
N2 C3 H3 . . 124.4 ?
N4 C3 H3 . . 124.4 ?
C3 N4 C5 . . 107.61(15) ?
C3 N4 H4 . . 126.2 ?
C5 N4 H4 . . 126.2 ?
C6 C5 N4 . . 106.21(16) ?
C6 C5 H5 . . 126.9 ?
N4 C5 H5 . . 126.9 ?
C5 C6 N2 . . 109.13(16) ?
C5 C6 H6 . . 125.4 ?
N2 C6 H6 . . 125.4 ?
C11 N7 C8 . . 105.94(15) ?
C11 N7 Cu1 . . 123.34(12) ?
C8 N7 Cu1 . . 129.56(12) ?
C9 C8 N7 . . 109.11(16) ?
C9 C8 H8 . . 125.4 ?
N7 C8 H8 . . 125.4 ?
C8 C9 N10 . . 106.00(17) ?
C8 C9 H9 . . 127.0 ?
N10 C9 H9 . . 127.0 ?
C11 N10 C9 . . 107.73(15) ?
C11 N10 H10 . . 126.1 ?
C9 N10 H10 . . 126.1 ?
N7 C11 N10 . . 111.22(16) ?
N7 C11 H11 . . 124.4 ?
N10 C11 H11 . . 124.4 ?
O12 C13 O14 . . 122.31(16) ?
O12 C13 C15 . . 118.91(16) ?
O14 C13 C15 . . 118.78(15) ?
C13 O14 H14 . . 112.2 ?
C23 C15 C16 . . 106.14(14) ?
C23 C15 C13 . . 129.32(16) ?
C16 C15 C13 . . 124.54(15) ?
C21 C16 C17 . . 118.86(16) ?
C21 C16 C15 . . 105.25(15) ?
C17 C16 C15 . . 135.88(16) ?
C18 C17 C16 . . 117.65(17) ?
C18 C17 H17 . . 121.2 ?
C16 C17 H17 . . 121.2 ?
C17 C18 C19 . . 121.99(17) ?
C17 C18 H18 . . 119.0 ?
C19 C18 H18 . . 119.0 ?
C20 C19 C18 . . 121.32(17) ?
C20 C19 H19 . . 119.3 ?
C18 C19 H19 . . 119.3 ?
C21 C20 C19 . . 115.76(17) ?
C21 C20 H20 . . 122.1 ?
C19 C20 H20 . . 122.1 ?
O22 C21 C20 . . 124.88(16) ?
O22 C21 C16 . . 110.70(14) ?
C20 C21 C16 . . 124.42(16) ?
C23 O22 C21 . . 106.19(13) ?
C15 C23 O22 . . 111.71(15) ?
C15 C23 C24 . . 133.42(15) ?
O22 C23 C24 . . 114.87(14) ?
O25 C24 O26 . . 124.71(16) ?
O25 C24 C23 . . 118.13(15) ?
O26 C24 C23 . . 117.16(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N2 2 2.0095(14) ?
Cu1 N2 . 2.0095(14) ?
Cu1 N7 . 2.0146(15) ?
Cu1 N7 2 2.0146(15) ?
N2 C3 . 1.324(2) ?
N2 C6 . 1.380(2) ?
C3 N4 . 1.336(2) ?
C3 H3 . 0.9500 ?
N4 C5 . 1.375(2) ?
N4 H4 . 0.8800 ?
C5 C6 . 1.358(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
N7 C11 . 1.321(2) ?
N7 C8 . 1.379(2) ?
C8 C9 . 1.365(3) ?
C8 H8 . 0.9500 ?
C9 N10 . 1.371(2) ?
C9 H9 . 0.9500 ?
N10 C11 . 1.339(2) ?
N10 H10 . 0.8800 ?
C11 H11 . 0.9500 ?
O12 C13 . 1.226(2) ?
C13 O14 . 1.304(2) ?
C13 C15 . 1.489(2) ?
O14 H14 . 0.9508 ?
C15 C23 . 1.367(2) ?
C15 C16 . 1.451(2) ?
C16 C21 . 1.395(2) ?
C16 C17 . 1.403(2) ?
C17 C18 . 1.386(3) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.402(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.388(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.388(2) ?
C20 H20 . 0.9500 ?
C21 O22 . 1.377(2) ?
O22 C23 . 1.371(2) ?
C23 C24 . 1.495(2) ?
C24 O25 . 1.243(2) ?
C24 O26 . 1.272(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O14 H14 O26 . 0.95 1.49 2.4380(17) 174
N4 H4 O25 2_666 0.88 1.98 2.779(2) 150
N10 H10 O25 1_454 0.88 1.99 2.799(2) 153
