#------------------------------------------------------------------------------
#$Date: 2023-12-01 18:11:06 +0200 (Fri, 01 Dec 2023) $
#$Revision: 287938 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/16/7221659.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_7221659
loop_
_publ_author_name
'Zhang, Zhong'
'Feng, Yan-Fang'
'Wei, Qiu-Yu'
'Hu, Kun'
'Chen, Zi-Lu'
'Liang, Fu-Pei'
_publ_section_title
;
 Metal-controlled structural variations of coordination architectures
 constructed from flexible 1H-benzimidazole-1-propionic acid
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              6724
_journal_paper_doi               10.1039/C5CE01250C
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H18 N4 O4 Zn'
_chemical_formula_sum            'C20 H18 N4 O4 Zn'
_chemical_formula_weight         443.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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
_audit_update_record
;
2015-06-13 deposited with the CCDC.
2015-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.025(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2788(2)
_cell_length_b                   8.36930(10)
_cell_length_c                   16.8959(4)
_cell_measurement_reflns_used    6040
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      3.01
_cell_volume                     1836.51(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14749
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    1.374
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0271(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0349
_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)+(0.0397P)²+1.0200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0887
_reflns_number_gt                3218
_reflns_number_total             3803
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce01250c2.cif
_cod_data_source_block           66
_cod_depositor_comments
'Adding full bibliography for 7221656--7221661.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7221659
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
C1 C 0.89385(15) 0.6369(3) 0.99681(13) 0.0328(5) Uani 1 1 d .
C2 C 0.9042(2) 0.7314(3) 0.93113(16) 0.0441(6) Uani 1 1 d .
H2 H 0.9459 0.8218 0.9375 0.053 Uiso 1 1 calc R
C3 C 0.8502(2) 0.6848(3) 0.85703(15) 0.0493(6) Uani 1 1 d .
H3 H 0.8552 0.7454 0.8119 0.059 Uiso 1 1 calc R
C4 C 0.78750(19) 0.5492(3) 0.84671(15) 0.0482(6) Uani 1 1 d .
H4 H 0.7532 0.5205 0.7949 0.058 Uiso 1 1 calc R
C5 C 0.77554(18) 0.4573(3) 0.91171(14) 0.0402(5) Uani 1 1 d .
H5 H 0.7325 0.3685 0.9049 0.048 Uiso 1 1 calc R
C6 C 0.83029(15) 0.5021(2) 0.98803(13) 0.0322(5) Uani 1 1 d .
C7 C 0.89828(17) 0.5266(3) 1.11448(14) 0.0383(5) Uani 1 1 d .
H7 H 0.9157 0.5081 1.1699 0.046 Uiso 1 1 calc R
C8 C 1.01497(17) 0.7641(3) 1.11770(16) 0.0411(6) Uani 1 1 d .
H8A H 1.0432 0.8177 1.0763 0.049 Uiso 1 1 calc R
H8B H 1.0705 0.7057 1.1520 0.049 Uiso 1 1 calc R
H9A H 1.0343 0.9465 1.1990 0.049 Uiso 1 1 d R
H9B H 0.9425 0.8346 1.2067 0.049 Uiso 1 1 d R
C9 C 0.97567(17) 0.8886(3) 1.16822(14) 0.0401(5) Uani 1 1 d .
C10 C 0.90055(15) 1.0089(2) 1.12177(14) 0.0335(5) Uani 1 1 d .
C11 C 0.51895(15) 0.1030(2) 0.90209(13) 0.0321(5) Uani 1 1 d .
C12 C 0.41570(17) 0.1029(3) 0.86363(16) 0.0451(6) Uani 1 1 d .
H12 H 0.3913 0.0411 0.8179 0.054 Uiso 1 1 calc R
C13 C 0.35174(19) 0.1991(4) 0.89686(19) 0.0559(7) Uani 1 1 d .
H13 H 0.2821 0.2034 0.8727 0.067 Uiso 1 1 calc R
C14 C 0.3881(2) 0.2902(3) 0.96555(19) 0.0550(7) Uani 1 1 d .
H14 H 0.3423 0.3547 0.9857 0.066 Uiso 1 1 calc R
C15 C 0.49022(19) 0.2877(3) 1.00475(16) 0.0434(6) Uani 1 1 d .
H15 H 0.5140 0.3481 1.0511 0.052 Uiso 1 1 calc R
C16 C 0.55602(16) 0.1907(3) 0.97180(13) 0.0324(5) Uani 1 1 d .
C17 C 0.68390(16) 0.0579(2) 0.94434(13) 0.0331(5) Uani 1 1 d .
H17 H 0.7495 0.0162 0.9471 0.040 Uiso 1 1 calc R
C18 C 0.60046(18) -0.0866(3) 0.81719(13) 0.0368(5) Uani 1 1 d .
H18A H 0.5449 -0.1628 0.8148 0.044 Uiso 1 1 calc R
H18B H 0.6646 -0.1458 0.8254 0.044 Uiso 1 1 calc R
H19A H 0.5340 0.0849 0.7373 0.044 Uiso 1 1 d R
H19B H 0.5584 -0.0713 0.6942 0.044 Uiso 1 1 d R
C19 C 0.58537(17) 0.0028(3) 0.73756(13) 0.0367(5) Uani 1 1 d .
C20 C 0.68103(17) 0.0806(3) 0.71904(13) 0.0368(5) Uani 1 1 d .
N1 N 0.93619(13) 0.6493(2) 1.07831(11) 0.0350(4) Uani 1 1 d .
N2 N 0.83446(14) 0.4355(2) 1.06425(11) 0.0361(4) Uani 1 1 d .
N3 N 0.60274(13) 0.0210(2) 0.88554(10) 0.0312(4) Uani 1 1 d .
N4 N 0.66129(13) 0.1593(2) 0.99783(11) 0.0346(4) Uani 1 1 d .
O1 O 0.85126(13) 1.09217(19) 1.16490(10) 0.0462(4) Uani 1 1 d .
O2 O 0.89112(12) 1.0247(2) 1.04864(10) 0.0449(4) Uani 1 1 d .
O3 O 0.66078(13) 0.1848(2) 0.66235(10) 0.0487(4) Uani 1 1 d .
O4 O 0.76684(13) 0.0398(2) 0.75403(12) 0.0617(5) Uani 1 1 d .
Zn1 Zn 0.75883(2) 0.24399(3) 1.098033(15) 0.03599(12) Uani 1 1 d .
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
N1 C1 C2 131.8(2) . .
N1 C1 C6 106.14(18) . .
C2 C1 C6 122.1(2) . .
C3 C2 C1 116.7(2) . .
C3 C2 H2 121.7 . .
C1 C2 H2 121.7 . .
C2 C3 C4 122.2(2) . .
C2 C3 H3 118.9 . .
C4 C3 H3 118.9 . .
C5 C4 C3 121.3(2) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C4 C5 C6 117.6(2) . .
C4 C5 H5 121.2 . .
C6 C5 H5 121.2 . .
C5 C6 N2 131.3(2) . .
C5 C6 C1 120.2(2) . .
N2 C6 C1 108.54(19) . .
N2 C7 N1 113.7(2) . .
N2 C7 H7 123.1 . .
N1 C7 H7 123.1 . .
N1 C8 C9 114.19(18) . .
N1 C8 H8A 108.7 . .
C9 C8 H8A 108.7 . .
N1 C8 H8B 108.7 . .
C9 C8 H8B 108.7 . .
H8A C8 H8B 107.6 . .
C8 C9 C10 115.72(19) . .
C8 C9 H9A 108.3 . .
C10 C9 H9A 108.3 . .
C8 C9 H9B 108.4 . .
C10 C9 H9B 108.4 . .
H9A C9 H9B 107.4 . .
O2 C10 O1 123.9(2) . .
O2 C10 C9 120.9(2) . .
O1 C10 C9 115.2(2) . .
N3 C11 C16 106.01(18) . .
N3 C11 C12 131.4(2) . .
C16 C11 C12 122.5(2) . .
C13 C12 C11 116.3(2) . .
C13 C12 H12 121.9 . .
C11 C12 H12 121.9 . .
C12 C13 C14 121.8(2) . .
C12 C13 H13 119.1 . .
C14 C13 H13 119.1 . .
C15 C14 C13 122.0(2) . .
C15 C14 H14 119.0 . .
C13 C14 H14 119.0 . .
C14 C15 C16 116.9(2) . .
C14 C15 H15 121.5 . .
C16 C15 H15 121.5 . .
C11 C16 C15 120.5(2) . .
C11 C16 N4 108.75(18) . .
C15 C16 N4 130.8(2) . .
N4 C17 N3 113.16(18) . .
N4 C17 H17 123.4 . .
N3 C17 H17 123.4 . .
N3 C18 C19 112.03(17) . .
N3 C18 H18A 109.2 . .
C19 C18 H18A 109.2 . .
N3 C18 H18B 109.2 . .
C19 C18 H18B 109.2 . .
H18A C18 H18B 107.9 . .
C18 C19 C20 115.70(18) . .
C18 C19 H19A 108.5 . .
C20 C19 H19A 108.3 . .
C18 C19 H19B 108.4 . .
C20 C19 H19B 108.2 . .
H19A C19 H19B 107.5 . .
O4 C20 O3 125.7(2) . .
O4 C20 C19 121.2(2) . .
O3 C20 C19 113.09(19) . .
C7 N1 C1 106.45(18) . .
C7 N1 C8 126.2(2) . .
C1 N1 C8 127.12(19) . .
C7 N2 C6 105.13(19) . .
C7 N2 Zn1 124.50(16) . .
C6 N2 Zn1 130.34(15) . .
C17 N3 C11 106.97(17) . .
C17 N3 C18 127.54(18) . .
C11 N3 C18 125.48(18) . .
C17 N4 C16 105.10(17) . .
C17 N4 Zn1 126.76(14) . .
C16 N4 Zn1 128.11(14) . .
C10 O1 Zn1 111.00(14) . 1_565
C20 O3 Zn1 124.23(15) . 4_565
O1 Zn1 O3 106.72(7) 1_545 4_566
O1 Zn1 N4 117.97(7) 1_545 .
O3 Zn1 N4 100.76(7) 4_566 .
O1 Zn1 N2 112.76(7) 1_545 .
O3 Zn1 N2 109.91(8) 4_566 .
N4 Zn1 N2 107.89(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.379(3) .
C1 C2 1.393(3) .
C1 C6 1.398(3) .
C2 C3 1.364(4) .
C2 H2 0.9300 .
C3 C4 1.397(4) .
C3 H3 0.9300 .
C4 C5 1.377(3) .
C4 H4 0.9300 .
C5 C6 1.393(3) .
C5 H5 0.9300 .
C6 N2 1.394(3) .
C7 N2 1.311(3) .
C7 N1 1.345(3) .
C7 H7 0.9300 .
C8 N1 1.473(3) .
C8 C9 1.507(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 C10 1.516(3) .
C9 H9A 0.9710 .
C9 H9B 0.9694 .
C10 O2 1.223(3) .
C10 O1 1.282(3) .
C11 N3 1.385(3) .
C11 C16 1.388(3) .
C11 C12 1.389(3) .
C12 C13 1.372(4) .
C12 H12 0.9300 .
C13 C14 1.388(4) .
C13 H13 0.9300 .
C14 C15 1.379(4) .
C14 H14 0.9300 .
C15 C16 1.391(3) .
C15 H15 0.9300 .
C16 N4 1.400(3) .
C17 N4 1.319(3) .
C17 N3 1.341(3) .
C17 H17 0.9300 .
C18 N3 1.459(3) .
C18 C19 1.516(3) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.517(3) .
C19 H19A 0.9682 .
C19 H19B 0.9705 .
C20 O4 1.218(3) .
C20 O3 1.282(3) .
N2 Zn1 2.0351(18) .
N4 Zn1 2.0329(18) .
O1 Zn1 1.9544(16) 1_565
O3 Zn1 1.9546(16) 4_565
Zn1 O1 1.9544(16) 1_545
Zn1 O3 1.9546(16) 4_566
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_4
N1 C1 C2 C3 -179.8(2) .
C6 C1 C2 C3 -0.9(3) .
C1 C2 C3 C4 -0.1(4) .
C2 C3 C4 C5 1.4(4) .
C3 C4 C5 C6 -1.6(3) .
C4 C5 C6 N2 179.8(2) .
C4 C5 C6 C1 0.6(3) .
N1 C1 C6 C5 179.80(18) .
C2 C1 C6 C5 0.7(3) .
N1 C1 C6 N2 0.4(2) .
C2 C1 C6 N2 -178.73(19) .
N1 C8 C9 C10 -68.1(3) .
C8 C9 C10 O2 -15.5(3) .
C8 C9 C10 O1 165.94(19) .
N3 C11 C12 C13 179.5(2) .
C16 C11 C12 C13 2.1(3) .
C11 C12 C13 C14 -0.6(4) .
C12 C13 C14 C15 -0.8(4) .
C13 C14 C15 C16 0.7(4) .
N3 C11 C16 C15 179.9(2) .
C12 C11 C16 C15 -2.2(3) .
N3 C11 C16 N4 -1.1(2) .
C12 C11 C16 N4 176.9(2) .
C14 C15 C16 C11 0.7(3) .
C14 C15 C16 N4 -178.2(2) .
N3 C18 C19 C20 80.0(2) .
C18 C19 C20 O4 18.5(3) .
C18 C19 C20 O3 -164.15(19) .
N2 C7 N1 C1 -0.4(2) .
N2 C7 N1 C8 -175.13(19) .
C2 C1 N1 C7 179.0(2) .
C6 C1 N1 C7 0.0(2) .
C2 C1 N1 C8 -6.4(4) .
C6 C1 N1 C8 174.64(18) .
C9 C8 N1 C7 -76.0(3) .
C9 C8 N1 C1 110.4(2) .
N1 C7 N2 C6 0.6(2) .
N1 C7 N2 Zn1 -177.81(14) .
C5 C6 N2 C7 -179.9(2) .
C1 C6 N2 C7 -0.6(2) .
C5 C6 N2 Zn1 -1.6(3) .
C1 C6 N2 Zn1 177.70(14) .
N4 C17 N3 C11 -0.9(2) .
N4 C17 N3 C18 179.97(18) .
C16 C11 N3 C17 1.2(2) .
C12 C11 N3 C17 -176.6(2) .
C16 C11 N3 C18 -179.69(18) .
C12 C11 N3 C18 2.6(4) .
C19 C18 N3 C17 -110.1(2) .
C19 C18 N3 C11 71.0(3) .
N3 C17 N4 C16 0.3(2) .
N3 C17 N4 Zn1 178.46(14) .
C11 C16 N4 C17 0.5(2) .
C15 C16 N4 C17 179.5(2) .
C11 C16 N4 Zn1 -177.65(14) .
C15 C16 N4 Zn1 1.3(3) .
O2 C10 O1 Zn1 0.7(3) 1_565
C9 C10 O1 Zn1 179.21(14) 1_565
O4 C20 O3 Zn1 18.6(4) 4_565
C19 C20 O3 Zn1 -158.65(15) 4_565
C17 N4 Zn1 O1 -44.1(2) 1_545
C16 N4 Zn1 O1 133.68(17) 1_545
C17 N4 Zn1 O3 -159.73(18) 4_566
C16 N4 Zn1 O3 18.06(19) 4_566
C17 N4 Zn1 N2 85.08(19) .
C16 N4 Zn1 N2 -97.14(18) .
C7 N2 Zn1 O1 -52.88(19) 1_545
C6 N2 Zn1 O1 129.08(17) 1_545
C7 N2 Zn1 O3 66.06(19) 4_566
C6 N2 Zn1 O3 -111.98(18) 4_566
C7 N2 Zn1 N4 175.06(17) .
C6 N2 Zn1 N4 -2.98(19) .
