#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/89/2018913.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_2018913
loop_
_publ_author_name
'Patra, Ranjan'
'Goldberg, Israel'
_publ_section_title
;
 A one-dimensional coordination polymer of
 5-[(imidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid with CuII
 cations
;
_journal_coeditor_code           KU3092
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              344
_journal_page_last               347
_journal_paper_doi               10.1107/S0108270113005313
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Cu (C12 H9 N2 O4)2] , 2C3 H7 N O'
_chemical_formula_moiety         'C24 H18 Cu N4 O8, 2(C3 H7 N O)'
_chemical_formula_sum            'C30 H32 Cu N6 O10'
_chemical_formula_weight         700.17
_chemical_name_systematic
'catena-poly[[copper(II)-bis[μ-3-carboxy-5-[(imidazol-1-yl)methyl]benzoato]] dimethylformamide disolvate]'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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           SHELXL2012
_cell_angle_alpha                90
_cell_angle_beta                 105.2590(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.55550(10)
_cell_length_b                   21.9603(5)
_cell_length_c                   9.8497(2)
_cell_measurement_reflns_used    3437
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.83
_cell_volume                     1576.66(5)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material  'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1° φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12428
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.808
_diffrn_reflns_theta_min         2.835
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  0.8328
_exptl_absorpt_correction_T_min  0.8042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       prism
_exptl_crystal_F_000             726
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.888
_refine_diff_density_min         -0.569
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0892P)²+0.9016P], where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1552
_reflns_number_gt                2639
_reflns_number_total             3689
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ku3092.cif
_cod_data_source_block           I
_cod_database_code               2018913
_cod_database_fobs_code          2018913
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined by the
following loop, which should always be used as a source of symmetry information
in preference to the above space-group names. They are only intended as
comments.
;
_shelx_estimated_absorpt_t_min   0.804
_shelx_estimated_absorpt_t_max   0.833
_shelxl_version_number           .002012
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_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_occupancy
Cu Cu1 1.0000 0.0000 1.0000 0.01997(17) Uani d 1
O O2 0.8865(3) 0.01891(9) 0.7991(2) 0.0219(4) Uani d 1
O O3 1.0407(3) 0.10340(9) 0.8724(2) 0.0265(5) Uani d 1
C C4 0.9250(4) 0.07429(13) 0.7813(3) 0.0211(6) Uani d 1
C C5 0.8188(4) 0.10403(13) 0.6471(3) 0.0223(6) Uani d 1
C C6 0.8110(4) 0.16732(13) 0.6368(3) 0.0225(6) Uani d 1
H H6 0.8764 0.1915 0.7136 0.027 Uiso calc 1
C C7 0.7084(4) 0.19521(13) 0.5149(3) 0.0238(6) Uani d 1
C C8 0.7049(4) 0.26335(14) 0.5099(3) 0.0274(7) Uani d 1
O O9 0.7652(3) 0.29491(10) 0.6109(2) 0.0361(6) Uani d 1
O O10 0.6367(4) 0.28468(11) 0.3815(2) 0.0452(6) Uani d 1
H H10 0.6062 0.3213 0.3859 0.068 Uiso calc 1
C C11 0.6091(4) 0.16024(14) 0.4024(3) 0.0240(6) Uani d 1
H H11 0.5391 0.1795 0.3191 0.029 Uiso calc 1
C C12 0.6132(4) 0.09634(14) 0.4127(3) 0.0229(6) Uani d 1
C C13 0.7189(4) 0.06904(14) 0.5341(3) 0.0225(6) Uani d 1
H H13 0.7234 0.0259 0.5407 0.027 Uiso calc 1
C C14 0.5056(4) 0.05795(15) 0.2918(3) 0.0248(6) Uani d 1
H H14A 0.4991 0.0156 0.3247 0.030 Uiso calc 1
H H14B 0.3788 0.0738 0.2599 0.030 Uiso calc 1
N N15 0.5888(3) 0.05786(11) 0.1726(2) 0.0221(5) Uani d 1
C C16 0.7474(4) 0.03079(14) 0.1726(3) 0.0251(6) Uani d 1
H H16 0.8234 0.0099 0.2509 0.030 Uiso calc 1
N N17 0.7851(3) 0.03691(11) 0.0488(2) 0.0228(5) Uani d 1
C C18 0.6374(4) 0.06878(16) -0.0345(3) 0.0318(7) Uani d 1
H H18 0.6227 0.0796 -0.1302 0.038 Uiso calc 1
C C19 0.5170(4) 0.08215(16) 0.0423(3) 0.0313(7) Uani d 1
H H19 0.4052 0.1040 0.0114 0.038 Uiso calc 1
O O20 0.2857(5) 0.07385(14) 0.6088(3) 0.0649(9) Uani d 1
C C21 0.2918(6) 0.1295(2) 0.6124(5) 0.0593(12) Uani d 1
H H21 0.3629 0.1481 0.6962 0.071 Uiso calc 1
N N22 0.2068(4) 0.16587(16) 0.5085(4) 0.0501(9) Uani d 1
C C23 0.2170(7) 0.2311(2) 0.5154(8) 0.088(2) Uani d 1
H H23A 0.2934 0.2435 0.6079 0.132 Uiso calc 1
H H23B 0.0934 0.2480 0.5012 0.132 Uiso calc 1
H H23C 0.2713 0.2463 0.4419 0.132 Uiso calc 1
C C24 0.0989(6) 0.1401(3) 0.3784(6) 0.0689(14) Uani d 1
H H24A 0.1138 0.0958 0.3810 0.103 Uiso calc 1
H H24B 0.1402 0.1568 0.2997 0.103 Uiso calc 1
H H24C -0.0307 0.1503 0.3662 0.103 Uiso calc 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
O2 Cu1 O2 3_757 . 180.00(11)
O2 Cu1 N17 3_757 3_756 89.40(9)
O2 Cu1 N17 . 3_756 90.60(9)
O2 Cu1 N17 3_757 1_556 90.60(9)
O2 Cu1 N17 . 1_556 89.40(9)
N17 Cu1 N17 3_756 1_556 180.0
C4 O2 Cu1 . . 106.43(17)
O3 C4 O2 . . 122.1(3)
O3 C4 C5 . . 121.3(3)
O2 C4 C5 . . 116.6(2)
C6 C5 C13 . . 119.1(3)
C6 C5 C4 . . 120.0(3)
C13 C5 C4 . . 120.8(3)
C7 C6 C5 . . 120.4(3)
C7 C6 H6 . . 119.8
C5 C6 H6 . . 119.8
C6 C7 C11 . . 120.4(3)
C6 C7 C8 . . 118.1(3)
C11 C7 C8 . . 121.5(3)
O9 C8 O10 . . 123.8(3)
O9 C8 C7 . . 123.4(3)
O10 C8 C7 . . 112.7(3)
C8 O10 H10 . . 109.5
C7 C11 C12 . . 119.7(3)
C7 C11 H11 . . 120.2
C12 C11 H11 . . 120.2
C13 C12 C11 . . 119.4(3)
C13 C12 C14 . . 120.5(3)
C11 C12 C14 . . 120.2(3)
C12 C13 C5 . . 121.1(3)
C12 C13 H13 . . 119.5
C5 C13 H13 . . 119.5
N15 C14 C12 . . 112.1(2)
N15 C14 H14A . . 109.2
C12 C14 H14A . . 109.2
N15 C14 H14B . . 109.2
C12 C14 H14B . . 109.2
H14A C14 H14B . . 107.9
C16 N15 C19 . . 107.9(2)
C16 N15 C14 . . 124.9(2)
C19 N15 C14 . . 127.1(2)
N17 C16 N15 . . 111.3(3)
N17 C16 H16 . . 124.3
N15 C16 H16 . . 124.3
C16 N17 C18 . . 105.1(2)
C16 N17 Cu1 . 1_554 124.6(2)
C18 N17 Cu1 . 1_554 130.2(2)
C19 C18 N17 . . 109.4(3)
C19 C18 H18 . . 125.3
N17 C18 H18 . . 125.3
C18 C19 N15 . . 106.3(3)
C18 C19 H19 . . 126.8
N15 C19 H19 . . 126.8
O20 C21 N22 . . 125.0(5)
O20 C21 H21 . . 117.5
N22 C21 H21 . . 117.5
C21 N22 C23 . . 123.8(5)
C21 N22 C24 . . 119.8(4)
C23 N22 C24 . . 116.4(4)
N22 C23 H23A . . 109.5
N22 C23 H23B . . 109.5
H23A C23 H23B . . 109.5
N22 C23 H23C . . 109.5
H23A C23 H23C . . 109.5
H23B C23 H23C . . 109.5
N22 C24 H24A . . 109.5
N22 C24 H24B . . 109.5
H24A C24 H24B . . 109.5
N22 C24 H24C . . 109.5
H24A C24 H24C . . 109.5
H24B C24 H24C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 O2 3_757 1.9828(19)
Cu1 O2 . 1.9828(19)
Cu1 N17 3_756 1.983(2)
Cu1 N17 1_556 1.983(2)
Cu1 O3 . 2.652(2)
Cu1 O3 3_757 2.652(2)
O2 C4 . 1.273(3)
O3 C4 . 1.251(3)
C4 C5 . 1.503(4)
C5 C6 . 1.394(4)
C5 C13 . 1.399(4)
C6 C7 . 1.388(4)
C6 H6 . 0.9500
C7 C11 . 1.394(4)
C7 C8 . 1.497(4)
C8 O9 . 1.200(4)
C8 O10 . 1.319(4)
O10 H10 . 0.8400
C11 C12 . 1.407(4)
C11 H11 . 0.9500
C12 C13 . 1.387(4)
C12 C14 . 1.510(4)
C13 H13 . 0.9500
C14 N15 . 1.470(4)
C14 H14A . 0.9900
C14 H14B . 0.9900
N15 C16 . 1.338(4)
N15 C19 . 1.364(4)
C16 N17 . 1.330(4)
C16 H16 . 0.9500
N17 C18 . 1.388(4)
N17 Cu1 1_554 1.983(2)
C18 C19 . 1.359(4)
C18 H18 . 0.9500
C19 H19 . 0.9500
O20 C21 . 1.224(5)
C21 N22 . 1.323(6)
C21 H21 . 0.9500
N22 C23 . 1.435(6)
N22 C24 . 1.441(6)
C23 H23A . 0.9800
C23 H23B . 0.9800
C23 H23C . 0.9800
C24 H24A . 0.9800
C24 H24B . 0.9800
C24 H24C . 0.9800
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
O10 H10 O3 4_565 0.84 1.72 2.557(3) 172.8
