#------------------------------------------------------------------------------
#$Date: 2019-03-03 21:49:33 +0100 (Sun 03 de Mar de 2019) $
#$Revision: 213936 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/14/2021457.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_2021457
loop_
_publ_author_name
'Chen, Ning-Ning'
'Ni, Jian-Ning'
'Wang, Jun'
'Tao, Jian-Qing'
_publ_section_title
;
 A new two-dimensional ZnII coordination polymer based on
 1,3-bis(2-methyl-1H-imidazol-1-yl)benzene and
 5-nitrobenzene-1,3-dicarboxylic acid: synthesis, crystal structure and
 physical properties
;
_journal_coeditor_code           QS3078
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              196
_journal_page_last               199
_journal_paper_doi               10.1107/S2053229619000986
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          '[Zn (C8 H3 N1 O6) (C14 H14 N4)]'
_chemical_formula_moiety         'C22 H17 N5 O6 Zn'
_chemical_formula_sum            'C22 H17 N5 O6 Zn'
_chemical_formula_weight         512.80
_chemical_name_systematic
Poly[[μ-1,3-bis(2-methyl-1H-imidazol-1-yl)benzene](μ-5-nitrobenzene-1,3-dicarboxylato)zinc(II)]
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 110.912(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.568(6)
_cell_length_b                   13.324(7)
_cell_length_c                   14.207(7)
_cell_measurement_reflns_used    9121
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.73
_cell_volume                     2222.3(19)
_computing_cell_refinement
;
SMART (Bruker, 2001)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2009)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2010)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22595
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.166
_diffrn_source                   'x-ray tube'
_exptl_absorpt_coefficient_mu    1.155
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0402P)²+1.0538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0751
_reflns_number_gt                4022
_reflns_number_total             4359
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qs3078sup1.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2021457.cif.'
_cod_database_code               2021457
_cod_database_fobs_code          2021457
_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   0.793
_shelx_estimated_absorpt_t_max   0.828
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C22 1.13159(19) -0.11355(16) 0.7143(2) 0.0572(6) Uani d 1
H H22A 1.2090 -0.1085 0.7175 0.086 Uiso calc 1
H H22B 1.1292 -0.1060 0.7807 0.086 Uiso calc 1
H H22C 1.0868 -0.0617 0.6713 0.086 Uiso calc 1
C C21 1.08495(15) -0.21308(12) 0.67325(14) 0.0346(4) Uani d 1
N N4 1.14047(12) -0.28589(10) 0.64756(12) 0.0354(3) Uani d 1
C C20 1.06470(17) -0.36404(15) 0.6134(2) 0.0540(6) Uani d 1
H H20 1.0811 -0.4254 0.5904 0.065 Uiso calc 1
C C19 0.96355(19) -0.33822(16) 0.6184(2) 0.0613(7) Uani d 1
H H19 0.8979 -0.3772 0.5996 0.074 Uiso calc 1
N N3 0.97671(13) -0.24200(12) 0.65710(14) 0.0404(4) Uani d 1
C C17 0.89046(15) -0.17656(13) 0.66832(15) 0.0383(4) Uani d 1
C C16 0.87098(18) -0.17327(15) 0.75749(16) 0.0466(5) Uani d 1
H H16 0.9100 -0.2160 0.8103 0.056 Uiso calc 1
C C15 0.79188(19) -0.10500(16) 0.76769(16) 0.0495(5) Uani d 1
H H15 0.7768 -0.1033 0.8272 0.059 Uiso calc 1
Zn Zn1 0.69472(2) 0.27715(2) 0.34318(2) 0.02960(8) Uani d 1
O O1 0.63764(11) 0.40797(9) 0.36525(10) 0.0387(3) Uani d 1
O O2 0.76641(15) 0.39284(13) 0.51902(12) 0.0633(5) Uani d 1
O O3 0.39155(12) 0.70809(9) 0.28248(9) 0.0397(3) Uani d 1
O O4 0.42046(13) 0.83278(9) 0.39240(11) 0.0471(3) Uani d 1
O O6 0.74405(17) 0.61513(14) 0.78460(11) 0.0703(5) Uani d 1
O O5 0.61084(16) 0.72622(13) 0.75137(12) 0.0616(4) Uani d 1
N N1 0.67650(12) 0.15549(11) 0.42241(11) 0.0334(3) Uani d 1
N N2 0.70400(13) 0.02398(11) 0.52039(11) 0.0360(3) Uani d 1
N N5 0.66318(15) 0.66121(13) 0.72578(12) 0.0442(4) Uani d 1
C C1 0.68582(15) 0.43617(13) 0.45671(14) 0.0355(4) Uani d 1
C C18 0.83326(16) -0.11390(14) 0.58925(15) 0.0388(4) Uani d 1
H H18 0.8454 -0.1182 0.5285 0.047 Uiso calc 1
C C2 0.43737(14) 0.74757(13) 0.36904(12) 0.0297(3) Uani d 1
C C5 0.51988(13) 0.67903(12) 0.44649(12) 0.0284(3) Uani d 1
C C3 0.63867(14) 0.53008(12) 0.48752(13) 0.0299(3) Uani d 1
C C4 0.56069(14) 0.59160(12) 0.41710(12) 0.0292(3) Uani d 1
H H4 0.5353 0.5742 0.3493 0.035 Uiso calc 1
C C8 0.67298(14) 0.55369(13) 0.58900(13) 0.0324(3) Uani d 1
H H8 0.7243 0.5129 0.6372 0.039 Uiso calc 1
C C6 0.55464(15) 0.70326(12) 0.54799(13) 0.0318(3) Uani d 1
H H6 0.5284 0.7612 0.5691 0.038 Uiso calc 1
C C11 0.74495(15) 0.11483(13) 0.50702(14) 0.0353(4) Uani d 1
C C13 0.75728(15) -0.04436(13) 0.60172(14) 0.0359(4) Uani d 1
C C9 0.58795(15) 0.08804(14) 0.38118(14) 0.0378(4) Uani d 1
H H9 0.5269 0.0978 0.3212 0.045 Uiso calc 1
C C10 0.60323(16) 0.00658(14) 0.44041(14) 0.0396(4) Uani d 1
H H10 0.5563 -0.0494 0.4300 0.047 Uiso calc 1
C C14 0.73531(17) -0.03944(14) 0.68993(15) 0.0426(4) Uani d 1
H H14 0.6835 0.0070 0.6973 0.051 Uiso calc 1
C C7 0.62931(14) 0.63912(13) 0.61724(12) 0.0325(3) Uani d 1
C C12 0.85115(18) 0.16005(16) 0.57886(17) 0.0535(5) Uani d 1
H H12A 0.9161 0.1284 0.5709 0.080 Uiso calc 1
H H12B 0.8537 0.1503 0.6466 0.080 Uiso calc 1
H H12C 0.8522 0.2306 0.5655 0.080 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C21 C22 H22A . . 109.5
C21 C22 H22B . . 109.5
H22A C22 H22B . . 109.5
C21 C22 H22C . . 109.5
H22A C22 H22C . . 109.5
H22B C22 H22C . . 109.5
N4 C21 N3 . . 110.04(15)
N4 C21 C22 . . 126.32(17)
N3 C21 C22 . . 123.65(16)
C21 N4 C20 . . 106.60(15)
C21 N4 Zn1 . 3_756 124.56(12)
C20 N4 Zn1 . 3_756 128.83(12)
C19 C20 N4 . . 109.65(18)
C19 C20 H20 . . 125.2
N4 C20 H20 . . 125.2
C20 C19 N3 . . 106.12(18)
C20 C19 H19 . . 126.9
N3 C19 H19 . . 126.9
C21 N3 C19 . . 107.59(16)
C21 N3 C17 . . 123.96(16)
C19 N3 C17 . . 128.06(16)
C16 C17 C18 . . 121.29(17)
C16 C17 N3 . . 120.60(17)
C18 C17 N3 . . 118.01(17)
C17 C16 C15 . . 119.04(18)
C17 C16 H16 . . 120.5
C15 C16 H16 . . 120.5
C14 C15 C16 . . 120.66(19)
C14 C15 H15 . . 119.7
C16 C15 H15 . . 119.7
O1 Zn1 O3 . 2_645 116.79(6)
O1 Zn1 N4 . 3_756 111.28(6)
O3 Zn1 N4 2_645 3_756 107.83(6)
O1 Zn1 N1 . . 120.17(6)
O3 Zn1 N1 2_645 . 89.71(7)
N4 Zn1 N1 3_756 . 108.89(6)
C1 O1 Zn1 . . 110.96(11)
C2 O3 Zn1 . 2_655 126.90(12)
C11 N1 C9 . . 106.42(15)
C11 N1 Zn1 . . 131.79(12)
C9 N1 Zn1 . . 120.99(12)
C11 N2 C10 . . 108.43(15)
C11 N2 C13 . . 126.02(15)
C10 N2 C13 . . 125.52(15)
O5 N5 O6 . . 123.86(17)
O5 N5 C7 . . 117.93(16)
O6 N5 C7 . . 118.19(16)
O2 C1 O1 . . 124.40(16)
O2 C1 C3 . . 119.22(17)
O1 C1 C3 . . 116.38(15)
C17 C18 C13 . . 118.91(17)
C17 C18 H18 . . 120.5
C13 C18 H18 . . 120.5
O4 C2 O3 . . 125.76(16)
O4 C2 C5 . . 120.11(15)
O3 C2 C5 . . 114.13(15)
C6 C5 C4 . . 119.49(15)
C6 C5 C2 . . 119.58(14)
C4 C5 C2 . . 120.94(15)
C8 C3 C4 . . 119.51(15)
C8 C3 C1 . . 118.67(15)
C4 C3 C1 . . 121.81(15)
C3 C4 C5 . . 121.11(15)
C3 C4 H4 . . 119.4
C5 C4 H4 . . 119.4
C7 C8 C3 . . 118.69(15)
C7 C8 H8 . . 120.7
C3 C8 H8 . . 120.7
C7 C6 C5 . . 118.47(15)
C7 C6 H6 . . 120.8
C5 C6 H6 . . 120.8
N1 C11 N2 . . 109.74(16)
N1 C11 C12 . . 126.32(17)
N2 C11 C12 . . 123.94(16)
C14 C13 C18 . . 121.25(17)
C14 C13 N2 . . 120.98(16)
C18 C13 N2 . . 117.76(16)
C10 C9 N1 . . 110.18(16)
C10 C9 H9 . . 124.9
N1 C9 H9 . . 124.9
C9 C10 N2 . . 105.23(16)
C9 C10 H10 . . 127.4
N2 C10 H10 . . 127.4
C13 C14 C15 . . 118.80(17)
C13 C14 H14 . . 120.6
C15 C14 H14 . . 120.6
C8 C7 C6 . . 122.67(15)
C8 C7 N5 . . 118.08(15)
C6 C7 N5 . . 119.25(15)
C11 C12 H12A . . 109.5
C11 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C11 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C22 C21 . 1.483(3)
C22 H22A . 0.9600
C22 H22B . 0.9600
C22 H22C . 0.9600
C21 N4 . 1.320(2)
C21 N3 . 1.352(2)
N4 C20 . 1.377(2)
N4 Zn1 3_756 2.0315(18)
C20 C19 . 1.343(3)
C20 H20 . 0.9300
C19 N3 . 1.381(3)
C19 H19 . 0.9300
N3 C17 . 1.444(2)
C17 C16 . 1.374(3)
C17 C18 . 1.378(3)
C16 C15 . 1.393(3)
C16 H16 . 0.9300
C15 C14 . 1.389(3)
C15 H15 . 0.9300
Zn1 O1 . 1.9524(14)
Zn1 O3 2_645 1.9563(14)
Zn1 N4 3_756 2.0315(18)
Zn1 N1 . 2.0326(16)
O1 C1 . 1.279(2)
O2 C1 . 1.226(2)
O3 C2 . 1.271(2)
O3 Zn1 2_655 1.9563(14)
O4 C2 . 1.223(2)
O6 N5 . 1.226(2)
O5 N5 . 1.219(2)
N1 C11 . 1.319(2)
N1 C9 . 1.387(2)
N2 C11 . 1.355(2)
N2 C10 . 1.386(2)
N2 C13 . 1.435(2)
N5 C7 . 1.476(2)
C1 C3 . 1.514(2)
C18 C13 . 1.387(2)
C18 H18 . 0.9300
C2 C5 . 1.518(2)
C5 C6 . 1.387(2)
C5 C4 . 1.395(2)
C3 C8 . 1.385(2)
C3 C4 . 1.390(2)
C4 H4 . 0.9300
C8 C7 . 1.384(2)
C8 H8 . 0.9300
C6 C7 . 1.386(2)
C6 H6 . 0.9300
C11 C12 . 1.488(3)
C13 C14 . 1.378(3)
C9 C10 . 1.344(3)
C9 H9 . 0.9300
C10 H10 . 0.9300
C14 H14 . 0.9300
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
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
C12 H12C O2 . 0.96 2.40 3.291(3) 154.1
C9 H9 O3 2_645 0.93 2.54 2.908(2) 103.8
C10 H10 O4 1_545 0.93 2.24 3.160(3) 170.8
C22 H22A O3 4_666 0.96 2.52 3.308(3) 138.9
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_site_symmetry_4
_geom_torsion
N3 C21 N4 C20 . . 0.2(2)
C22 C21 N4 C20 . . 180.0(2)
N3 C21 N4 Zn1 . 3_756 179.29(13)
C22 C21 N4 Zn1 . 3_756 -0.9(3)
C21 N4 C20 C19 . . 0.1(3)
Zn1 N4 C20 C19 3_756 . -178.92(17)
N4 C20 C19 N3 . . -0.4(3)
N4 C21 N3 C19 . . -0.4(2)
C22 C21 N3 C19 . . 179.8(2)
N4 C21 N3 C17 . . -173.85(17)
C22 C21 N3 C17 . . 6.4(3)
C20 C19 N3 C21 . . 0.5(3)
C20 C19 N3 C17 . . 173.5(2)
C21 N3 C17 C16 . . -94.0(2)
C19 N3 C17 C16 . . 94.0(3)
C21 N3 C17 C18 . . 82.5(3)
C19 N3 C17 C18 . . -89.6(3)
C18 C17 C16 C15 . . -0.1(3)
N3 C17 C16 C15 . . 176.22(19)
C17 C16 C15 C14 . . -1.5(3)
Zn1 O1 C1 O2 . . 8.1(2)
Zn1 O1 C1 C3 . . -172.39(11)
C16 C17 C18 C13 . . 2.0(3)
N3 C17 C18 C13 . . -174.43(17)
Zn1 O3 C2 O4 2_655 . 12.5(3)
Zn1 O3 C2 C5 2_655 . -167.11(11)
O4 C2 C5 C6 . . 15.5(2)
O3 C2 C5 C6 . . -164.86(15)
O4 C2 C5 C4 . . -164.98(16)
O3 C2 C5 C4 . . 14.7(2)
O2 C1 C3 C8 . . -12.1(3)
O1 C1 C3 C8 . . 168.31(16)
O2 C1 C3 C4 . . 169.14(18)
O1 C1 C3 C4 . . -10.4(2)
C8 C3 C4 C5 . . 2.7(2)
C1 C3 C4 C5 . . -178.62(15)
C6 C5 C4 C3 . . -2.2(2)
C2 C5 C4 C3 . . 178.21(15)
C4 C3 C8 C7 . . -0.8(2)
C1 C3 C8 C7 . . -179.55(15)
C4 C5 C6 C7 . . 0.0(2)
C2 C5 C6 C7 . . 179.52(15)
C9 N1 C11 N2 . . 0.68(19)
Zn1 N1 C11 N2 . . -168.85(12)
C9 N1 C11 C12 . . -178.95(19)
Zn1 N1 C11 C12 . . 11.5(3)
C10 N2 C11 N1 . . -0.8(2)
C13 N2 C11 N1 . . 177.48(16)
C10 N2 C11 C12 . . 178.89(19)
C13 N2 C11 C12 . . -2.9(3)
C17 C18 C13 C14 . . -2.3(3)
C17 C18 C13 N2 . . 176.34(16)
C11 N2 C13 C14 . . 89.3(2)
C10 N2 C13 C14 . . -92.7(2)
C11 N2 C13 C18 . . -89.3(2)
C10 N2 C13 C18 . . 88.6(2)
C11 N1 C9 C10 . . -0.4(2)
Zn1 N1 C9 C10 . . 170.53(12)
N1 C9 C10 N2 . . -0.1(2)
C11 N2 C10 C9 . . 0.5(2)
C13 N2 C10 C9 . . -177.75(16)
C18 C13 C14 C15 . . 0.8(3)
N2 C13 C14 C15 . . -177.86(18)
C16 C15 C14 C13 . . 1.2(3)
C3 C8 C7 C6 . . -1.5(3)
C3 C8 C7 N5 . . 177.69(16)
C5 C6 C7 C8 . . 1.9(3)
C5 C6 C7 N5 . . -177.26(15)
O5 N5 C7 C8 . . -168.03(18)
O6 N5 C7 C8 . . 13.9(3)
O5 N5 C7 C6 . . 11.2(3)
O6 N5 C7 C6 . . -166.90(19)
