#------------------------------------------------------------------------------
#$Date: 2018-09-18 01:47:52 +0300 (Tue, 18 Sep 2018) $
#$Revision: 211033 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/15/7231526.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_7231526
loop_
_publ_author_name
'Behera, Jogendra Nath'
'Tiwari, Ranjay K.'
_publ_section_title
;
 Hybrid materials based on transition Metal-BTC-Benzimidazole: Solvent
 assisted crystallographic and structural switching
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C8CE01299G
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H9 N2 O6 Zn, C4 H12 N, H2 O'
_chemical_formula_sum            'C20 H23 N3 O7 Zn'
_chemical_formula_weight         482.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc1pycpp
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-08-03 deposited with the CCDC.
2018-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6345(8)
_cell_length_b                   11.2144(5)
_cell_length_c                   12.7553(6)
_cell_measurement_reflns_used    4158
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.5
_cell_measurement_theta_min      2.2
_cell_volume                     2236.41(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.235
_exptl_absorpt_coefficient_mu    1.143
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.004(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0237
_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)+(0.0399P)²+0.2194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0653
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3920
_reflns_number_total             4158
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01299g2.cif
_cod_data_source_block           5
_cod_database_code               7231526
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Zn1 Zn 0.39596(2) 0.33968(2) 0.46948(4) 0.02973(11) Uani 1 1 d . .
O1 O 0.47774(15) 0.27503(19) 0.57023(19) 0.0400(5) Uani 1 1 d . .
O4 O 0.62977(17) -0.2260(2) 0.8541(2) 0.0481(6) Uani 1 1 d . .
O5 O 0.83117(16) 0.0323(2) 0.6426(2) 0.0528(7) Uani 1 1 d . .
O6 O 0.77578(15) 0.1241(2) 0.50641(18) 0.0431(6) Uani 1 1 d . .
N1 N 0.46301(18) 0.4771(2) 0.4067(2) 0.0395(7) Uani 1 1 d . .
O2 O 0.38494(18) 0.1352(3) 0.6100(4) 0.0718(11) Uani 1 1 d . .
C5 C 0.6807(2) 0.0457(3) 0.6335(2) 0.0339(7) Uani 1 1 d . .
C4 C 0.6668(2) -0.0447(3) 0.7071(2) 0.0356(7) Uani 1 1 d . .
H4 H 0.7125 -0.0909 0.7301 0.043 Uiso 1 1 calc R U
C7 C 0.4579(3) 0.1736(3) 0.6055(3) 0.0378(9) Uani 1 1 d . .
C6 C 0.6128(2) 0.1167(3) 0.6015(3) 0.0331(7) Uani 1 1 d . .
H6 H 0.6220 0.1771 0.5529 0.040 Uiso 1 1 calc R U
O3 O 0.4920(2) -0.1864(3) 0.8448(3) 0.0654(9) Uani 1 1 d . .
C3 C 0.5856(2) -0.0656(3) 0.7456(3) 0.0359(7) Uani 1 1 d . .
C2 C 0.5184(2) 0.0070(3) 0.7135(3) 0.0353(8) Uani 1 1 d . .
H2 H 0.4639 -0.0056 0.7404 0.042 Uiso 1 1 calc R U
C8 C 0.5667(3) -0.1657(3) 0.8205(3) 0.0422(10) Uani 1 1 d . .
C1 C 0.5320(2) 0.0984(3) 0.6413(3) 0.0334(7) Uani 1 1 d . .
C15 C 0.4783(2) 0.5936(3) 0.4398(2) 0.0393(8) Uani 1 1 d . .
C9 C 0.7694(2) 0.0682(3) 0.5926(3) 0.0357(7) Uani 1 1 d . .
N2 N 0.5499(2) 0.5629(3) 0.2945(3) 0.0617(10) Uani 1 1 d . .
H2A H 0.5820 0.5715 0.2402 0.074 Uiso 1 1 calc R U
C16 C 0.5330(3) 0.6487(3) 0.3690(3) 0.0507(10) Uani 1 1 d . .
N3 N 0.7495(4) 0.0143(6) 0.1418(5) 0.1099(19) Uani 1 1 d . .
H3A H 0.7309 0.0531 0.1982 0.132 Uiso 1 1 calc R U
H3B H 0.7077 -0.0348 0.1223 0.132 Uiso 1 1 calc R U
C11 C 0.5601(4) 0.7649(4) 0.3808(4) 0.0706(13) Uani 1 1 d . .
H11 H 0.5960 0.8010 0.3322 0.085 Uiso 1 1 calc R U
C14 C 0.4493(4) 0.6556(4) 0.5268(3) 0.0610(12) Uani 1 1 d . .
H14 H 0.4132 0.6202 0.5757 0.073 Uiso 1 1 calc R U
C12 C 0.5314(4) 0.8244(4) 0.4673(7) 0.0892(16) Uani 1 1 d . .
H12 H 0.5497 0.9021 0.4792 0.107 Uiso 1 1 calc R U
C10 C 0.5080(3) 0.4653(4) 0.3213(3) 0.0545(10) Uani 1 1 d . .
H10 H 0.5103 0.3949 0.2829 0.065 Uiso 1 1 calc R U
C13 C 0.4759(4) 0.7715(5) 0.5378(5) 0.0902(18) Uani 1 1 d . .
H13 H 0.4560 0.8159 0.5944 0.108 Uiso 1 1 calc R U
O1W O 0.6771(4) 0.1351(10) 0.3137(5) 0.208(5) Uani 1 1 d G .
H1WA H 0.7203 0.1219 0.3524 0.313 Uiso 1 1 d G U
H1WB H 0.6382 0.0905 0.3386 0.313 Uiso 1 1 d G U
C18 C 0.7987(6) -0.1379(10) 0.2618(8) 0.145(4) Uani 1 1 d . .
H18A H 0.7545 -0.1919 0.2400 0.217 Uiso 1 1 calc R U
H18B H 0.7786 -0.0911 0.3198 0.217 Uiso 1 1 calc R U
H18C H 0.8482 -0.1825 0.2828 0.217 Uiso 1 1 calc R U
C17 C 0.8208(5) -0.0599(12) 0.1754(11) 0.164(4) Uani 1 1 d . .
H17A H 0.8401 -0.1079 0.1167 0.197 Uiso 1 1 calc R U
H17B H 0.8679 -0.0090 0.1966 0.197 Uiso 1 1 calc R U
C19 C 0.7600(10) 0.1086(19) 0.0526(9) 0.245(8) Uani 1 1 d . .
H19A H 0.8125 0.1539 0.0598 0.294 Uiso 1 1 calc R U
H19B H 0.7116 0.1627 0.0492 0.294 Uiso 1 1 calc R U
C20 C 0.7630(13) 0.019(2) -0.0477(10) 0.43(2) Uani 1 1 d . .
H20A H 0.7751 -0.0607 -0.0241 0.641 Uiso 1 1 calc R U
H20B H 0.8069 0.0443 -0.0953 0.641 Uiso 1 1 calc R U
H20C H 0.7087 0.0200 -0.0829 0.641 Uiso 1 1 calc R U
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
O1 Zn1 O6 122.77(11) . 3_455
O1 Zn1 O4 112.44(10) . 2_654
O6 Zn1 O4 96.64(11) 3_455 2_654
O1 Zn1 N1 101.73(11) . .
O6 Zn1 N1 115.39(11) 3_455 .
O4 Zn1 N1 107.43(12) 2_654 .
C7 O1 Zn1 114.1(2) . .
C8 O4 Zn1 115.7(3) . 2_655
C9 O6 Zn1 112.4(2) . 3
C10 N1 C15 104.8(3) . .
C10 N1 Zn1 122.1(3) . .
C15 N1 Zn1 132.9(2) . .
C6 C5 C4 119.7(3) . .
C6 C5 C9 120.5(3) . .
C4 C5 C9 119.8(3) . .
C3 C4 C5 120.3(3) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
O2 C7 O1 124.3(4) . .
O2 C7 C1 120.5(3) . .
O1 C7 C1 115.2(3) . .
C1 C6 C5 120.5(3) . .
C1 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
C4 C3 C2 119.3(3) . .
C4 C3 C8 122.3(3) . .
C2 C3 C8 118.4(3) . .
C3 C2 C1 120.7(3) . .
C3 C2 H2 119.7 . .
C1 C2 H2 119.7 . .
O3 C8 O4 123.5(3) . .
O3 C8 C3 119.2(4) . .
O4 C8 C3 117.3(4) . .
C6 C1 C2 119.5(3) . .
C6 C1 C7 120.7(3) . .
C2 C1 C7 119.8(3) . .
C14 C15 C16 119.9(3) . .
C14 C15 N1 131.1(3) . .
C16 C15 N1 109.0(3) . .
O5 C9 O6 123.5(3) . .
O5 C9 C5 119.4(3) . .
O6 C9 C5 117.1(3) . .
C10 N2 C16 107.8(3) . .
C10 N2 H2A 126.1 . .
C16 N2 H2A 126.1 . .
N2 C16 C11 132.6(4) . .
N2 C16 C15 104.8(3) . .
C11 C16 C15 122.6(4) . .
C17 N3 C19 121.4(9) . .
C17 N3 H3A 107.0 . .
C19 N3 H3A 107.0 . .
C17 N3 H3B 107.0 . .
C19 N3 H3B 107.0 . .
H3A N3 H3B 106.7 . .
C12 C11 C16 116.7(5) . .
C12 C11 H11 121.6 . .
C16 C11 H11 121.6 . .
C13 C14 C15 117.3(5) . .
C13 C14 H14 121.4 . .
C15 C14 H14 121.4 . .
C11 C12 C13 121.5(4) . .
C11 C12 H12 119.3 . .
C13 C12 H12 119.3 . .
N1 C10 N2 113.6(4) . .
N1 C10 H10 123.2 . .
N2 C10 H10 123.2 . .
C14 C13 C12 122.0(5) . .
C14 C13 H13 119.0 . .
C12 C13 H13 119.0 . .
H1WA O1W H1WB 104.5 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C18 C17 N3 112.7(8) . .
C18 C17 H17A 109.1 . .
N3 C17 H17A 109.1 . .
C18 C17 H17B 109.1 . .
N3 C17 H17B 109.1 . .
H17A C17 H17B 107.8 . .
N3 C19 C20 99.0(14) . .
N3 C19 H19A 112.0 . .
C20 C19 H19A 112.0 . .
N3 C19 H19B 112.0 . .
C20 C19 H19B 112.0 . .
H19A C19 H19B 109.6 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.952(2) .
Zn1 O6 1.979(2) 3_455
Zn1 O4 1.988(2) 2_654
Zn1 N1 2.028(3) .
O1 C7 1.262(4) .
O4 C8 1.270(5) .
O4 Zn1 1.988(2) 2_655
O5 C9 1.226(4) .
O6 C9 1.269(4) .
O6 Zn1 1.979(2) 3
N1 C10 1.304(5) .
N1 C15 1.393(4) .
O2 C7 1.221(5) .
C5 C6 1.387(4) .
C5 C4 1.399(4) .
C5 C9 1.504(5) .
C4 C3 1.382(5) .
C4 H4 0.9300 .
C7 C1 1.503(5) .
C6 C1 1.378(5) .
C6 H6 0.9300 .
O3 C8 1.230(6) .
C3 C2 1.391(5) .
C3 C8 1.504(5) .
C2 C1 1.393(5) .
C2 H2 0.9300 .
C15 C14 1.386(5) .
C15 C16 1.389(5) .
N2 C10 1.321(5) .
N2 C16 1.378(5) .
N2 H2A 0.8600 .
C16 C11 1.378(6) .
N3 C17 1.456(12) .
N3 C19 1.562(15) .
N3 H3A 0.8900 .
N3 H3B 0.8900 .
C11 C12 1.365(9) .
C11 H11 0.9300 .
C14 C13 1.372(6) .
C14 H14 0.9300 .
C12 C13 1.383(9) .
C12 H12 0.9300 .
C10 H10 0.9300 .
C13 H13 0.9300 .
O1W H1WA 0.8500 .
O1W H1WB 0.8499 .
C18 C17 1.449(15) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C19 C20 1.63(2) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
