#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:09:31 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179559 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/28/4502829.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_4502829
loop_
_publ_author_name
'Li, Yun-Wu'
'Ma, Hong'
'Chen, Yong-Qiang'
'He, Kun-Huan'
'Li, Zuo-Xi'
'Bu, Xian-He'
_publ_section_title
;
 Structure Modulation in Zn(II)--1,4-Bis(imidazol-1-yl)benzene Frameworks
 by Varying Dicarboxylate Anions
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              189
_journal_paper_doi               10.1021/cg200926z
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C14 H10 N3 O4 Zn'
_chemical_formula_weight         349.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.48(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1487(16)
_cell_length_b                   14.991(3)
_cell_length_c                   11.733(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1351.2(5)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  SCX-MINI
_diffrn_measurement_method       multi-scan
_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  0.1567
_diffrn_reflns_av_sigmaI/netI    0.1201
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11242
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    1.840
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.332
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1400
_refine_ls_R_factor_gt           0.0819
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²+2.8374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1720
_reflns_number_gt                1527
_reflns_number_total             2373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200926z_si_002.cif
_cod_data_source_block           2
_cod_original_cell_volume        1351.2(4)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4502829
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Zn1 Zn 0.00783(11) 0.02351(6) 0.15197(8) 0.0267(3) Uani 1 1 d .
O1 O 0.0454(9) 0.1777(4) 0.2622(6) 0.058(2) Uani 1 1 d .
O2 O 0.2012(7) 0.1061(4) 0.1713(5) 0.0421(16) Uani 1 1 d .
O3 O 0.7881(7) 0.4465(4) 0.5265(5) 0.0381(15) Uani 1 1 d .
O4 O 0.8789(7) 0.4113(4) 0.3732(5) 0.0392(16) Uani 1 1 d .
N2 N -0.0771(8) -0.0208(5) 0.2829(6) 0.0310(16) Uani 1 1 d .
N1 N -0.2371(8) -0.0340(4) 0.3997(6) 0.0282(16) Uani 1 1 d .
N3 N 0.2039(11) 0.3022(6) 0.4257(8) 0.064(3) Uani 1 1 d .
H3B H 0.2141 0.3382 0.4848 0.076 Uiso 1 1 calc R
H3C H 0.1126 0.2694 0.3983 0.076 Uiso 1 1 calc R
C13 C 0.1823(12) 0.1703(6) 0.2368(8) 0.035(2) Uani 1 1 d .
C7 C 0.3285(10) 0.2347(5) 0.2850(7) 0.029(2) Uani 1 1 d .
C12 C 0.4690(10) 0.2296(6) 0.2421(7) 0.034(2) Uani 1 1 d .
H12A H 0.4656 0.1884 0.1821 0.041 Uiso 1 1 calc R
C11 C 0.6128(11) 0.2843(6) 0.2868(7) 0.035(2) Uani 1 1 d .
H11A H 0.7055 0.2798 0.2576 0.042 Uiso 1 1 calc R
C10 C 0.6166(10) 0.3467(5) 0.3768(7) 0.029(2) Uani 1 1 d .
C9 C 0.4780(10) 0.3509(5) 0.4216(7) 0.0270(19) Uani 1 1 d .
H9A H 0.4831 0.3905 0.4837 0.032 Uiso 1 1 calc R
C8 C 0.3337(10) 0.2971(5) 0.3752(7) 0.027(2) Uani 1 1 d .
C14 C 0.7742(10) 0.4053(5) 0.4306(8) 0.030(2) Uani 1 1 d .
C5 C -0.0252(10) -0.0950(6) 0.3555(7) 0.032(2) Uani 1 1 d .
H5A H 0.0631 -0.1339 0.3541 0.038 Uiso 1 1 calc R
C6 C -0.1204(10) -0.1029(5) 0.4277(8) 0.032(2) Uani 1 1 d .
H6A H -0.1097 -0.1467 0.4859 0.038 Uiso 1 1 calc R
C4 C -0.2063(11) 0.0136(6) 0.3121(8) 0.036(2) Uani 1 1 d .
H4A H -0.2681 0.0643 0.2767 0.043 Uiso 1 1 calc R
C1 C -0.3707(10) -0.0154(6) 0.4509(7) 0.033(2) Uani 1 1 d .
C3 C -0.4563(11) -0.0873(6) 0.4810(7) 0.034(2) Uani 1 1 d .
H3A H -0.4266 -0.1454 0.4679 0.040 Uiso 1 1 calc R
C2 C -0.4145(11) 0.0717(6) 0.4697(8) 0.038(2) Uani 1 1 d .
H2A H -0.3568 0.1194 0.4491 0.046 Uiso 1 1 calc R
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'
Zn Zn 0.2839 1.4301 '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
O3 Zn1 O2 116.2(3) 4_465 .
O3 Zn1 O4 115.9(3) 4_465 2_645
O2 Zn1 O4 99.0(2) . 2_645
O3 Zn1 N2 101.0(2) 4_465 .
O2 Zn1 N2 126.4(3) . .
O4 Zn1 N2 97.4(3) 2_645 .
O3 Zn1 O1 95.5(2) 4_465 .
O2 Zn1 O1 55.0(2) . .
O4 Zn1 O1 146.9(2) 2_645 .
N2 Zn1 O1 85.8(3) . .
C13 O1 Zn1 76.8(5) . .
C13 O2 Zn1 107.1(5) . .
C14 O3 Zn1 125.0(5) . 4_666
C14 O4 Zn1 124.9(5) . 2_655
C4 N2 C5 105.2(6) . .
C4 N2 Zn1 125.6(6) . .
C5 N2 Zn1 129.1(5) . .
C4 N1 C6 107.1(6) . .
C4 N1 C1 125.4(7) . .
C6 N1 C1 127.5(7) . .
C8 N3 H3B 120.0 . .
C8 N3 H3C 120.0 . .
H3B N3 H3C 120.0 . .
O1 C13 O2 120.5(8) . .
O1 C13 C7 121.1(8) . .
O2 C13 C7 118.4(8) . .
C12 C7 C8 119.1(7) . .
C12 C7 C13 118.4(8) . .
C8 C7 C13 122.5(7) . .
C11 C12 C7 121.6(8) . .
C11 C12 H12A 119.2 . .
C7 C12 H12A 119.2 . .
C12 C11 C10 118.9(8) . .
C12 C11 H11A 120.5 . .
C10 C11 H11A 120.5 . .
C9 C10 C11 119.7(7) . .
C9 C10 C14 119.9(7) . .
C11 C10 C14 120.3(7) . .
C8 C9 C10 121.0(7) . .
C8 C9 H9A 119.5 . .
C10 C9 H9A 119.5 . .
N3 C8 C9 118.3(8) . .
N3 C8 C7 121.9(8) . .
C9 C8 C7 119.7(7) . .
O4 C14 O3 124.9(8) . .
O4 C14 C10 117.0(8) . .
O3 C14 C10 118.0(7) . .
C6 C5 N2 110.0(7) . .
C6 C5 H5A 125.0 . .
N2 C5 H5A 125.0 . .
C5 C6 N1 106.6(7) . .
C5 C6 H6A 126.7 . .
N1 C6 H6A 126.7 . .
N2 C4 N1 111.2(7) . .
N2 C4 H4A 124.4 . .
N1 C4 H4A 124.4 . .
C2 C1 C3 120.7(8) . .
C2 C1 N1 121.3(7) . .
C3 C1 N1 118.0(8) . .
C2 C3 C1 119.5(8) 3_456 .
C2 C3 H3A 120.3 3_456 .
C1 C3 H3A 120.3 . .
C3 C2 C1 119.8(8) 3_456 .
C3 C2 H2A 120.1 3_456 .
C1 C2 H2A 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O3 1.954(6) 4_465
Zn1 O2 1.957(5) .
Zn1 O4 1.987(5) 2_645
Zn1 N2 1.997(6) .
Zn1 O1 2.616(7) .
O1 C13 1.252(10) .
O2 C13 1.273(10) .
O3 C14 1.255(9) .
O3 Zn1 1.954(6) 4_666
O4 C14 1.254(9) .
O4 Zn1 1.987(5) 2_655
N2 C4 1.316(9) .
N2 C5 1.379(10) .
N1 C4 1.341(10) .
N1 C6 1.367(9) .
N1 C1 1.436(10) .
N3 C8 1.376(10) .
N3 H3B 0.8600 .
N3 H3C 0.8600 .
C13 C7 1.490(11) .
C7 C12 1.398(11) .
C7 C8 1.403(11) .
C12 C11 1.382(11) .
C12 H12A 0.9300 .
C11 C10 1.404(11) .
C11 H11A 0.9300 .
C10 C9 1.397(10) .
C10 C14 1.510(11) .
C9 C8 1.379(10) .
C9 H9A 0.9300 .
C5 C6 1.332(10) .
C5 H5A 0.9300 .
C6 H6A 0.9300 .
C4 H4A 0.9300 .
C1 C2 1.391(12) .
C1 C3 1.392(11) .
C3 C2 1.381(11) 3_456
C3 H3A 0.9300 .
C2 C3 1.381(11) 3_456
C2 H2A 0.9300 .
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_4
O3 Zn1 O1 C13 -123.0(5) 4_465 .
O2 Zn1 O1 C13 -4.7(5) . .
O4 Zn1 O1 C13 39.1(7) 2_645 .
N2 Zn1 O1 C13 136.3(5) . .
O3 Zn1 O2 C13 82.4(6) 4_465 .
O4 Zn1 O2 C13 -152.8(5) 2_645 .
N2 Zn1 O2 C13 -46.5(7) . .
O1 Zn1 O2 C13 4.7(5) . .
O3 Zn1 N2 C4 -39.4(7) 4_465 .
O2 Zn1 N2 C4 95.2(7) . .
O4 Zn1 N2 C4 -157.8(7) 2_645 .
O1 Zn1 N2 C4 55.4(7) . .
O3 Zn1 N2 C5 135.7(7) 4_465 .
O2 Zn1 N2 C5 -89.6(7) . .
O4 Zn1 N2 C5 17.4(7) 2_645 .
O1 Zn1 N2 C5 -129.5(7) . .
Zn1 O1 C13 O2 6.9(7) . .
Zn1 O1 C13 C7 -171.3(8) . .
Zn1 O2 C13 O1 -9.4(10) . .
Zn1 O2 C13 C7 168.9(6) . .
O1 C13 C7 C12 -172.4(8) . .
O2 C13 C7 C12 9.3(12) . .
O1 C13 C7 C8 10.4(12) . .
O2 C13 C7 C8 -167.9(8) . .
C8 C7 C12 C11 0.3(12) . .
C13 C7 C12 C11 -177.0(8) . .
C7 C12 C11 C10 -0.4(13) . .
C12 C11 C10 C9 1.6(12) . .
C12 C11 C10 C14 177.9(8) . .
C11 C10 C9 C8 -2.7(12) . .
C14 C10 C9 C8 -179.1(7) . .
C10 C9 C8 N3 177.9(8) . .
C10 C9 C8 C7 2.6(12) . .
C12 C7 C8 N3 -176.5(8) . .
C13 C7 C8 N3 0.7(12) . .
C12 C7 C8 C9 -1.4(11) . .
C13 C7 C8 C9 175.8(7) . .
Zn1 O4 C14 O3 -39.5(12) 2_655 .
Zn1 O4 C14 C10 138.1(6) 2_655 .
Zn1 O3 C14 O4 -33.8(12) 4_666 .
Zn1 O3 C14 C10 148.6(6) 4_666 .
C9 C10 C14 O4 -167.0(7) . .
C11 C10 C14 O4 16.6(11) . .
C9 C10 C14 O3 10.7(11) . .
C11 C10 C14 O3 -165.6(8) . .
C4 N2 C5 C6 -1.2(9) . .
Zn1 N2 C5 C6 -177.1(6) . .
N2 C5 C6 N1 1.2(9) . .
C4 N1 C6 C5 -0.7(9) . .
C1 N1 C6 C5 178.2(8) . .
C5 N2 C4 N1 0.8(9) . .
Zn1 N2 C4 N1 176.9(5) . .
C6 N1 C4 N2 -0.1(10) . .
C1 N1 C4 N2 -179.0(7) . .
C4 N1 C1 C2 -37.1(12) . .
C6 N1 C1 C2 144.1(8) . .
C4 N1 C1 C3 142.6(9) . .
C6 N1 C1 C3 -36.2(12) . .
C2 C1 C3 C2 -0.2(14) . 3_456
N1 C1 C3 C2 -179.9(7) . 3_456
C3 C1 C2 C3 0.2(14) . 3_456
N1 C1 C2 C3 179.9(8) . 3_456
