#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/46/2014659.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_2014659
loop_
_publ_author_name
'Bai, Yue-Ling'
'Tao, Jun'
'Huang, Rong-Bin'
'Zheng, Lan-Sun'
_publ_section_title
;
 A three-dimensional supramolecular network built with the zigzag chain
 complex bis(5-carboxy-1H-imidazole-4-carboxylato)copper(II)
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m98
_journal_page_last               m100
_journal_paper_doi               10.1107/S0108270104034158
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Cu (C10 H6 N4 O8)]'
_chemical_formula_moiety         'C10 H6 Cu N4 O8'
_chemical_formula_sum            'C10 H6 Cu N4 O8'
_chemical_formula_weight         373.73
_chemical_name_systematic
;
poly[copper(II)-μ-5-carboxy-1H-imidazole-4-carboxylato],
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.65(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1120(10)
_cell_length_b                   14.676(3)
_cell_length_c                   12.145(2)
_cell_measurement_reflns_used    2318
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3.18
_cell_volume                     1259.1(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction
'teXsan (Molecular Structure Corporation & Rigaku Corporation, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 1997) in WinGX (Farrugia, 1999)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4554
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    1.791
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.376
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.1086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                2318
_reflns_number_total             3038
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1804.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2014659
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
Cu1 0.38859(5) 0.57768(3) 0.61124(3) 0.02405(12) Uani d . 1 . . Cu
O1 0.5549(3) 0.61073(16) 0.49365(17) 0.0271(5) Uani d . 1 . . O
O2 0.5450(3) 0.69413(16) 0.33820(17) 0.0297(5) Uani d . 1 . . O
O3 0.2731(3) 0.77558(18) 0.20750(19) 0.0373(6) Uani d . 1 . . O
H3 0.3585 0.7533 0.2502 0.045 Uiso calc R 1 . . H
O4 -0.0463(3) 0.78344(16) 0.19586(19) 0.0364(6) Uani d . 1 . . O
N1 -0.0564(3) 0.67896(18) 0.3874(2) 0.0271(6) Uani d . 1 . . N
H1 -0.1691 0.6935 0.3595 0.033 Uiso calc R 1 . . H
N3 0.1800(3) 0.62062(19) 0.4997(2) 0.0259(5) Uani d . 1 . . N
C2 -0.0097(4) 0.6333(2) 0.4825(2) 0.0292(7) Uani d . 1 . . C
H2 -0.0952 0.6134 0.5296 0.035 Uiso calc R 1 . . H
C4 0.2560(4) 0.6611(2) 0.4129(2) 0.0222(6) Uani d . 1 . . C
C5 0.1096(4) 0.6985(2) 0.3421(2) 0.0233(6) Uani d . 1 . . C
C6 0.4674(4) 0.6563(2) 0.4138(2) 0.0233(6) Uani d . 1 . . C
C7 0.1067(4) 0.7553(2) 0.2418(3) 0.0298(7) Uani d . 1 . . C
O11 0.6017(3) 0.51959(15) 0.71053(16) 0.0275(5) Uani d . 1 . . O
O12 0.6598(3) 0.44032(16) 0.86885(18) 0.0322(5) Uani d . 1 . . O
O13 0.4420(4) 0.3655(2) 1.0074(2) 0.0453(7) Uani d . 1 . . O
H13 0.5063 0.3800 0.9583 0.054 Uiso calc R 1 . . H
O14 0.1284(4) 0.3671(2) 1.0292(2) 0.0488(7) Uani d . 1 . . O
N11 0.0408(4) 0.47378(19) 0.8368(2) 0.0307(6) Uani d . 1 . . N
H11 -0.0599 0.4608 0.8665 0.037 Uiso calc R 1 . . H
N13 0.2295(3) 0.52994(18) 0.7218(2) 0.0257(5) Uani d . 1 . . N
C12 0.0488(4) 0.5242(2) 0.7457(3) 0.0320(7) Uani d . 1 . . C
H12 -0.0548 0.5514 0.7048 0.038 Uiso calc R 1 . . H
C14 0.3387(4) 0.4817(2) 0.8027(2) 0.0233(6) Uani d . 1 . . C
C15 0.2235(4) 0.4461(2) 0.8752(2) 0.0247(6) Uani d . 1 . . C
C16 0.5482(4) 0.4798(2) 0.7956(2) 0.0246(6) Uani d . 1 . . C
C17 0.2592(5) 0.3895(3) 0.9771(3) 0.0348(7) Uani d . 1 . . C
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'
S S 0.1246 0.1234 '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'
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
N13 Cu1 N3 . . 97.68(10) y
N13 Cu1 O11 . . 83.90(9) y
N3 Cu1 O11 . . 172.26(10) y
N13 Cu1 O1 . . 173.20(10) y
N3 Cu1 O1 . . 83.93(9) y
O11 Cu1 O1 . . 93.64(8) y
N13 Cu1 O4 . 4_676 96.40(10) ?
N3 Cu1 O4 . 4_676 96.82(10) ?
O11 Cu1 O4 . 4_676 90.51(9) ?
O1 Cu1 O4 . 4_676 89.95(9) ?
O1 Cu1 O4 3_666 4_676 161.07(9) y
C6 O1 Cu1 . . 112.91(18) ?
C7 O3 H3 . . 109.5 ?
C7 O4 Cu1 . 4_575 128.2(2) ?
C2 N1 C5 . . 107.8(2) ?
C2 N1 H1 . . 126.1 ?
C5 N1 H1 . . 126.1 ?
C2 N3 C4 . . 107.2(2) ?
C2 N3 Cu1 . . 143.1(2) ?
C4 N3 Cu1 . . 109.27(18) ?
N1 C2 N3 . . 110.2(3) ?
N1 C2 H2 . . 124.9 ?
N3 C2 H2 . . 124.9 ?
N3 C4 C5 . . 108.3(2) ?
N3 C4 C6 . . 117.2(2) ?
C5 C4 C6 . . 134.6(3) ?
C4 C5 N1 . . 106.5(2) ?
C4 C5 C7 . . 132.5(3) ?
N1 C5 C7 . . 120.9(3) ?
O2 C6 O1 . . 124.8(3) ?
O2 C6 C4 . . 119.9(3) ?
O1 C6 C4 . . 115.3(2) ?
O4 C7 O3 . . 123.5(3) ?
O4 C7 C5 . . 119.3(3) ?
O3 C7 C5 . . 117.2(3) ?
C16 O11 Cu1 . . 113.71(18) ?
C17 O13 H13 . . 109.5 ?
C12 N11 C15 . . 108.2(2) ?
C12 N11 H11 . . 125.9 ?
C15 N11 H11 . . 125.9 ?
C12 N13 C14 . . 106.7(2) ?
C12 N13 Cu1 . . 143.0(2) ?
C14 N13 Cu1 . . 110.26(18) ?
N11 C12 N13 . . 110.2(3) ?
N11 C12 H12 . . 124.9 ?
N13 C12 H12 . . 124.9 ?
C15 C14 N13 . . 108.9(2) ?
C15 C14 C16 . . 134.4(3) ?
N13 C14 C16 . . 116.7(2) ?
C14 C15 N11 . . 106.1(3) ?
C14 C15 C17 . . 133.5(3) ?
N11 C15 C17 . . 120.4(3) ?
O12 C16 O11 . . 123.7(3) ?
O12 C16 C14 . . 121.0(3) ?
O11 C16 C14 . . 115.3(2) ?
O14 C17 O13 . . 123.4(3) ?
O14 C17 C15 . . 120.7(3) ?
O13 C17 C15 . . 115.9(3) ?
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 N13 . 1.982(3) y
Cu1 N3 . 1.992(2) y
Cu1 O11 . 2.014(2) y
Cu1 O1 . 2.016(2) y
Cu1 O4 4_676 2.305(2) y
Cu1 O1 3_666 3.090(2) y
O1 C6 . 1.279(4) ?
O2 C6 . 1.254(4) ?
O3 C7 . 1.333(4) ?
O3 H3 . 0.82 ?
O4 C7 . 1.235(4) ?
O4 Cu1 4_575 2.305(2) ?
N1 C2 . 1.343(4) ?
N1 C5 . 1.389(4) ?
N1 H1 . 0.86 ?
N3 C2 . 1.354(4) ?
N3 C4 . 1.374(4) ?
C2 H2 . 0.93 ?
C4 C5 . 1.385(4) ?
C4 C6 . 1.505(4) ?
C5 C7 . 1.475(4) ?
O11 C16 . 1.283(4) ?
O12 C16 . 1.262(3) ?
O13 C17 . 1.356(4) ?
O13 H13 . 0.82 ?
O14 C17 . 1.229(4) ?
N11 C12 . 1.338(4) ?
N11 C15 . 1.389(4) ?
N11 H11 . 0.86 ?
N13 C12 . 1.352(4) ?
N13 C14 . 1.376(4) ?
C12 H12 . 0.93 ?
C14 C15 . 1.374(4) ?
C14 C16 . 1.502(4) ?
C15 C17 . 1.487(4) ?
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
O3 H3 O2 . 0.82 1.82 2.642(3) 175
O13 H13 O12 . 0.82 1.85 2.653(3) 165
N1 H1 O2 1_455 0.86 2.02 2.837(3) 158
N11 H11 O12 1_455 0.86 2.02 2.825(3) 156
C2 H2 O1 1_455 0.93 2.48 3.133(4) 128
C12 H12 O11 1_455 0.93 2.50 3.160(4) 129
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_site_symmetry_1
_geom_torsion
N3 Cu1 O1 C6 . 11.1(2)
O11 Cu1 O1 C6 . -176.2(2)
O4 Cu1 O1 C6 4_676 -85.7(2)
N13 Cu1 N3 C2 . 7.7(4)
O1 Cu1 N3 C2 . -179.0(4)
O4 Cu1 N3 C2 4_676 -89.7(4)
N13 Cu1 N3 C4 . 177.9(2)
O1 Cu1 N3 C4 . -8.8(2)
O4 Cu1 N3 C4 4_676 80.4(2)
C5 N1 C2 N3 . -1.4(4)
C4 N3 C2 N1 . 1.0(4)
Cu1 N3 C2 N1 . 171.2(3)
C2 N3 C4 C5 . -0.2(3)
Cu1 N3 C4 C5 . -174.0(2)
C2 N3 C4 C6 . 179.8(3)
Cu1 N3 C4 C6 . 5.9(3)
N3 C4 C5 N1 . -0.6(3)
C6 C4 C5 N1 . 179.5(3)
N3 C4 C5 C7 . 174.6(3)
C6 C4 C5 C7 . -5.3(6)
C2 N1 C5 C4 . 1.2(4)
C2 N1 C5 C7 . -174.7(3)
Cu1 O1 C6 O2 . 170.8(2)
Cu1 O1 C6 C4 . -10.6(3)
N3 C4 C6 O2 . -178.1(3)
C5 C4 C6 O2 . 1.8(5)
N3 C4 C6 O1 . 3.2(4)
C5 C4 C6 O1 . -176.9(3)
Cu1 O4 C7 O3 4_575 -34.9(5)
Cu1 O4 C7 C5 4_575 143.2(2)
C4 C5 C7 O4 . -176.8(3)
N1 C5 C7 O4 . -2.2(5)
C4 C5 C7 O3 . 1.3(5)
N1 C5 C7 O3 . 176.0(3)
N13 Cu1 O11 C16 . 0.0(2)
O1 Cu1 O11 C16 . -173.6(2)
O4 Cu1 O11 C16 4_676 96.4(2)
N3 Cu1 N13 C12 . -6.2(4)
O11 Cu1 N13 C12 . -178.5(4)
O4 Cu1 N13 C12 4_676 91.6(4)
N3 Cu1 N13 C14 . 170.3(2)
O11 Cu1 N13 C14 . -2.0(2)
O4 Cu1 N13 C14 4_676 -91.9(2)
C15 N11 C12 N13 . 0.7(4)
C14 N13 C12 N11 . -0.7(4)
Cu1 N13 C12 N11 . 175.8(3)
C12 N13 C14 C15 . 0.5(4)
Cu1 N13 C14 C15 . -177.3(2)
C12 N13 C14 C16 . -178.6(3)
Cu1 N13 C14 C16 . 3.6(3)
N13 C14 C15 N11 . -0.1(3)
C16 C14 C15 N11 . 178.8(3)
N13 C14 C15 C17 . -179.7(3)
C16 C14 C15 C17 . -0.8(6)
C12 N11 C15 C14 . -0.4(4)
C12 N11 C15 C17 . 179.3(3)
Cu1 O11 C16 O12 . -179.1(2)
Cu1 O11 C16 C14 . 1.9(3)
C15 C14 C16 O12 . -1.7(6)
N13 C14 C16 O12 . 177.1(3)
C15 C14 C16 O11 . 177.4(3)
N13 C14 C16 O11 . -3.7(4)
C14 C15 C17 O14 . 179.0(4)
N11 C15 C17 O14 . -0.6(5)
C14 C15 C17 O13 . -0.9(6)
N11 C15 C17 O13 . 179.6(3)
