#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/53/2205320.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_2205320
loop_
_publ_author_name
'Gao, Shan'
'Huo, Li-Hua'
'Liu, Ji-Wei'
'Gu, Chang-Sheng'
_publ_section_title
catena-Poly[[bis(1H-benzimidazole-κN³)zinc(II)]-μ-3-carboxyphenoxyacetato-κ²O:O']
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m494
_journal_page_last               m495
_journal_paper_doi               10.1107/S1600536805003661
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Zn (C9 H6 O5) (C7 H6 N2)2]'
_chemical_formula_moiety         'C23 H18 N4 O5 Zn'
_chemical_formula_sum            'C23 H18 N4 O5 Zn'
_chemical_formula_weight         495.80
_chemical_name_systematic
;catena-Poly[[bis(1H-benzimidazole-\kN³)zinc(II)]-μ-3-carboxyphenoxyacetato-
κ²O:O']
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                116.06(2)
_cell_angle_beta                 100.32(2)
_cell_angle_gamma                104.936(14)
_cell_formula_units_Z            2
_cell_length_a                   10.580(3)
_cell_length_b                   11.356(3)
_cell_length_c                   11.492(3)
_cell_measurement_reflns_used    8851
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.42
_cell_volume                     1128.4(6)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10127
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.130
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0715P)²+0.3509P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                3129
_reflns_number_total             5055
_reflns_threshold_expression     I>2σ(I)'
_cod_data_source_file            ng6101.cif
_cod_data_source_block           I
_cod_database_code               2205320
_cod_database_fobs_code          2205320
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Zn1 0.74550(5) 0.89735(5) 0.68338(5) 0.05213(19) Uani d . 1 Zn
O1 0.8747(3) 0.8960(3) 0.8255(3) 0.0618(8) Uani d . 1 O
O2 0.8601(3) 0.6840(3) 0.6722(3) 0.0648(8) Uani d . 1 O
O3 0.9940(3) 0.6508(3) 0.8778(3) 0.0633(8) Uani d . 1 O
O4 0.7018(3) 0.0702(3) 0.7632(3) 0.0621(8) Uani d . 1 O
O5 0.9159(3) 0.1644(3) 0.7723(3) 0.0596(7) Uani d . 1 O
N1 0.5598(3) 0.7461(3) 0.6316(3) 0.0532(8) Uani d . 1 N
N2 0.3532(4) 0.5726(4) 0.5123(4) 0.0736(11) Uani d . 1 N
N3 0.7845(3) 0.8594(3) 0.5080(3) 0.0534(8) Uani d . 1 N
N4 0.9021(4) 0.8260(4) 0.3624(4) 0.0598(9) Uani d . 1 N
C1 0.4721(5) 0.6476(5) 0.5084(5) 0.0641(11) Uani d . 1 C
C2 0.4941(4) 0.7354(4) 0.7238(4) 0.0535(10) Uani d . 1 C
C3 0.5368(5) 0.8156(5) 0.8656(5) 0.0701(12) Uani d . 1 C
C4 0.4463(6) 0.7845(7) 0.9298(6) 0.0977(19) Uani d . 1 C
C5 0.3156(7) 0.6766(7) 0.8547(7) 0.0983(18) Uani d . 1 C
C6 0.2712(6) 0.5965(6) 0.7155(7) 0.0877(16) Uani d . 1 C
C7 0.3644(5) 0.6274(4) 0.6507(5) 0.0614(11) Uani d . 1 C
C8 0.8739(5) 0.8060(4) 0.4632(4) 0.0571(10) Uani d . 1 C
C9 0.7527(4) 0.9218(4) 0.4316(4) 0.0531(10) Uani d . 1 C
C10 0.6675(5) 0.9974(5) 0.4371(5) 0.0660(12) Uani d . 1 C
C11 0.6634(5) 1.0514(6) 0.3517(6) 0.0813(15) Uani d . 1 C
C12 0.7383(5) 1.0324(5) 0.2624(6) 0.0766(14) Uani d . 1 C
C13 0.8208(5) 0.9568(5) 0.2539(5) 0.0678(12) Uani d . 1 C
C14 0.8274(4) 0.9014(4) 0.3399(4) 0.0546(10) Uani d . 1 C
C15 0.8993(4) 0.7841(4) 0.7909(4) 0.0528(10) Uani d . 1 C
C16 0.9893(5) 0.7856(4) 0.9107(5) 0.0645(12) Uani d . 1 C
C17 0.8795(4) 0.5500(4) 0.8631(4) 0.0523(10) Uani d . 1 C
C18 0.7565(5) 0.5656(4) 0.8766(5) 0.0616(11) Uani d . 1 C
C19 0.6478(5) 0.4537(5) 0.8582(5) 0.0671(12) Uani d . 1 C
C20 0.6589(5) 0.3245(5) 0.8251(5) 0.0597(11) Uani d . 1 C
C21 0.7840(4) 0.3102(4) 0.8158(4) 0.0497(9) Uani d . 1 C
C22 0.8927(4) 0.4221(4) 0.8339(4) 0.0505(9) Uani d . 1 C
C23 0.8044(5) 0.1736(4) 0.7828(4) 0.0509(9) Uani d . 1 C
H1 0.4901 0.6314 0.4276 0.077 Uiso calc R 1 H
H3 0.6240 0.8883 0.9161 0.084 Uiso calc R 1 H
H4 0.4732 0.8366 1.0253 0.117 Uiso calc R 1 H
H5 0.2568 0.6588 0.9013 0.118 Uiso calc R 1 H
H6 0.1834 0.5247 0.6656 0.105 Uiso calc R 1 H
H8 0.9138 0.7590 0.4978 0.068 Uiso calc R 1 H
H10 0.6157 1.0106 0.4959 0.079 Uiso calc R 1 H
H11 0.6078 1.1032 0.3537 0.098 Uiso calc R 1 H
H12 0.7322 1.0721 0.2071 0.092 Uiso calc R 1 H
H13 0.8705 0.9430 0.1932 0.081 Uiso calc R 1 H
H16A 1.0831 0.8531 0.9411 0.077 Uiso calc R 1 H
H16B 0.9540 0.8179 0.9865 0.077 Uiso calc R 1 H
H18 0.7471 0.6513 0.8982 0.074 Uiso calc R 1 H
H19 0.5657 0.4651 0.8680 0.081 Uiso calc R 1 H
H20 0.5839 0.2486 0.8094 0.072 Uiso calc R 1 H
H22 0.9758 0.4118 0.8266 0.061 Uiso calc R 1 H
H24 0.2833 0.5037 0.4425 0.088 Uiso calc R 1 H
H25 0.9567 0.7971 0.3197 0.072 Uiso calc R 1 H
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
_geom_angle_publ_flag
O1 Zn1 O4 . 1_565 110.49(12) yes
O1 Zn1 N1 . . 105.98(13) yes
O1 Zn1 N3 . . 119.11(13) yes
O4 Zn1 N1 1_565 . 100.62(12) yes
O4 Zn1 N3 1_565 . 111.56(12) yes
N3 Zn1 N1 . . 107.20(14) yes
O1 C15 C16 . . 113.4(4) no
O2 C15 O1 . . 125.0(4) no
O2 C15 C16 . . 121.5(4) no
O3 C16 C15 . . 113.4(3) no
O3 C16 H16A . . 108.9 no
O3 C16 H16B . . 108.9 no
O3 C17 C18 . . 126.0(3) no
O3 C17 C22 . . 114.8(4) no
O4 C23 C21 . . 117.5(4) no
O5 C23 O4 . . 122.8(3) no
O5 C23 C21 . . 119.8(4) no
N1 C1 N2 . . 112.4(4) no
N1 C1 H1 . . 123.8 no
N2 C1 H1 . . 123.8 no
N2 C7 C6 . . 132.5(5) no
N3 C8 N4 . . 113.4(4) no
N3 C8 H8 . . 123.3 no
N3 C9 C14 . . 108.8(4) no
N4 C8 H8 . . 123.3 no
N4 C14 C9 . . 105.5(3) no
N4 C14 C13 . . 132.6(4) no
C1 N1 Zn1 . . 128.4(3) no
C1 N1 C2 . . 105.9(4) no
C1 N2 C7 . . 107.3(4) no
C1 N2 H24 . . 126.3 no
C2 N1 Zn1 . . 125.4(3) no
C2 C3 H3 . . 121.0 no
C2 C7 N2 . . 105.2(4) no
C2 C7 C6 . . 122.1(5) no
C3 C2 N1 . . 130.7(4) no
C3 C4 C5 . . 121.1(5) no
C3 C4 H4 . . 119.4 no
C4 C3 C2 . . 118.0(5) no
C4 C3 H3 . . 121.0 no
C4 C5 H5 . . 119.0 no
C5 C4 H4 . . 119.4 no
C5 C6 C7 . . 116.6(5) no
C5 C6 H6 . . 121.7 no
C6 C5 C4 . . 122.0(5) no
C6 C5 H5 . . 119.0 no
C7 N2 H24 . . 126.3 no
C7 C2 C3 . . 120.1(4) no
C7 C2 N1 . . 109.1(4) no
C7 C6 H6 . . 121.7 no
C8 N3 Zn1 . . 127.4(3) no
C8 N3 C9 . . 105.0(3) no
C8 N4 C14 . . 107.3(3) no
C8 N4 H25 . . 126.4 no
C9 N3 Zn1 . . 125.2(3) no
C9 C10 H10 . . 121.7 no
C10 C9 N3 . . 130.8(4) no
C10 C9 C14 . . 120.3(4) no
C10 C11 C12 . . 122.9(5) no
C10 C11 H11 . . 118.5 no
C11 C10 C9 . . 116.6(4) no
C11 C10 H10 . . 121.7 no
C11 C12 H12 . . 119.3 no
C12 C11 H11 . . 118.5 no
C12 C13 C14 . . 116.9(4) no
C12 C13 H13 . . 121.6 no
C13 C12 C11 . . 121.4(5) no
C13 C12 H12 . . 119.3 no
C13 C14 C9 . . 121.9(4) no
C14 N4 H25 . . 126.4 no
C14 C13 H13 . . 121.6 no
C15 O1 Zn1 . . 116.7(3) no
C15 C16 H16A . . 108.9 no
C15 C16 H16B . . 108.9 no
C17 O3 C16 . . 118.0(3) no
C17 C18 H18 . . 120.1 no
C17 C22 H22 . . 119.5 no
C18 C17 C22 . . 119.3(4) no
C18 C19 C20 . . 121.2(4) no
C18 C19 H19 . . 119.4 no
C19 C18 C17 . . 119.9(4) no
C19 C18 H18 . . 120.1 no
C19 C20 C21 . . 119.0(4) no
C19 C20 H20 . . 120.5 no
C20 C19 H19 . . 119.4 no
C20 C21 C23 . . 121.9(4) no
C21 C20 H20 . . 120.5 no
C21 C22 C17 . . 120.9(4) no
C21 C22 H22 . . 119.5 no
C22 C21 C20 . . 119.8(3) no
C22 C21 C23 . . 118.3(4) no
C23 O4 Zn1 . 1_545 107.7(2) no
H16A C16 H16B . . 107.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Zn1 O1 . 1.942(3) yes
Zn1 O4 1_565 1.986(3) yes
Zn1 N1 . 2.027(3) yes
Zn1 N3 . 2.011(3) yes
O1 C15 . 1.266(4) yes
O2 C15 . 1.231(5) yes
O4 C23 . 1.277(5) yes
O5 C23 . 1.232(5) yes
O3 C16 . 1.424(4) no
O3 C17 . 1.360(5) no
O4 Zn1 1_545 1.986(3) no
N1 C1 . 1.311(5) no
N1 C2 . 1.398(5) no
N2 C1 . 1.346(6) no
N2 C7 . 1.399(6) no
N2 H24 . 0.8600 no
N3 C8 . 1.313(5) no
N3 C9 . 1.397(5) no
N4 C8 . 1.343(5) no
N4 C14 . 1.377(5) no
N4 H25 . 0.8600 no
C1 H1 . 0.9300 no
C2 C7 . 1.381(6) no
C2 C3 . 1.381(6) no
C3 C4 . 1.377(7) no
C3 H3 . 0.9300 no
C4 C5 . 1.388(8) no
C4 H4 . 0.9300 no
C5 C6 . 1.356(8) no
C5 H5 . 0.9300 no
C6 C7 . 1.401(7) no
C6 H6 . 0.9300 no
C8 H8 . 0.9300 no
C9 C10 . 1.388(6) no
C9 C14 . 1.402(6) no
C10 C11 . 1.367(7) no
C10 H10 . 0.9300 no
C11 C12 . 1.383(7) no
C11 H11 . 0.9300 no
C12 C13 . 1.361(7) no
C12 H12 . 0.9300 no
C13 C14 . 1.386(6) no
C13 H13 . 0.9300 no
C15 C16 . 1.518(6) no
C16 H16A . 0.9700 no
C16 H16B . 0.9700 no
C17 C18 . 1.384(6) no
C17 C22 . 1.391(5) no
C18 C19 . 1.379(6) no
C18 H18 . 0.9300 no
C19 C20 . 1.389(6) no
C19 H19 . 0.9300 no
C20 C21 . 1.391(6) no
C20 H20 . 0.9300 no
C21 C22 . 1.382(5) no
C21 C23 . 1.511(5) no
C22 H22 . 0.9300 no
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
_geom_hbond_publ_flag
N2 H24 O2 2_666 0.86 1.93 2.747(5) 158 yes
N4 H25 O5 2_766 0.86 1.93 2.688(4) 146 yes
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
_geom_torsion_publ_flag
Zn1 O1 C15 O2 . 8.5(5) no
Zn1 O1 C15 C16 . -174.1(3) no
Zn1 O4 C23 O5 1_545 -10.1(5) no
Zn1 O4 C23 C21 1_545 167.9(3) no
Zn1 N1 C1 N2 . -174.6(3) no
Zn1 N1 C2 C3 . -2.8(6) no
Zn1 N1 C2 C7 . 174.7(3) no
Zn1 N3 C8 N4 . -164.1(3) no
Zn1 N3 C9 C10 . -14.3(6) no
Zn1 N3 C9 C14 . 164.0(3) no
O1 Zn1 N1 C2 . 52.6(3) no
O1 Zn1 N1 C1 . -133.8(4) no
O1 Zn1 N3 C8 . 14.4(4) no
O1 Zn1 N3 C9 . -145.6(3) no
O1 C15 C16 O3 . 168.1(4) no
O2 C15 C16 O3 . -14.4(6) no
O3 C17 C18 C19 . 179.6(4) no
O3 C17 C22 C21 . -179.7(4) no
O4 Zn1 N1 C1 1_565 111.1(4) no
O4 Zn1 N1 C2 1_565 -62.5(3) no
O4 Zn1 O1 C15 1_565 172.5(3) no
O4 Zn1 N3 C8 1_565 145.0(3) no
O4 Zn1 N3 C9 1_565 -15.0(4) no
N1 Zn1 N3 C8 . -105.7(3) no
N1 Zn1 N3 C9 . 94.3(3) no
N1 Zn1 O1 C15 . 64.4(3) no
N1 C2 C3 C4 . 177.0(5) no
N1 C2 C7 N2 . 0.2(5) no
N1 C2 C7 C6 . -176.6(4) no
N3 Zn1 N1 C1 . -5.6(4) no
N3 Zn1 N1 C2 . -179.2(3) no
N3 Zn1 O1 C15 . -56.4(3) no
N3 C9 C10 C11 . 176.9(4) no
N3 C9 C14 N4 . 0.4(4) no
N3 C9 C14 C13 . -177.5(4) no
C1 N1 C2 C3 . -177.6(5) no
C1 N1 C2 C7 . -0.1(5) no
C1 N2 C7 C2 . -0.2(5) no
C1 N2 C7 C6 . 176.2(5) no
C2 N1 C1 N2 . 0.0(5) no
C2 C3 C4 C5 . -0.5(9) no
C3 C2 C7 N2 . 178.0(4) no
C3 C2 C7 C6 . 1.2(7) no
C3 C4 C5 C6 . 0.5(10) no
C4 C5 C6 C7 . 0.4(9) no
C5 C6 C7 N2 . -177.0(5) no
C5 C6 C7 C2 . -1.2(8) no
C7 N2 C1 N1 . 0.1(5) no
C7 C2 C3 C4 . -0.3(7) no
C8 N3 C9 C10 . -178.0(5) no
C8 N3 C9 C14 . 0.3(4) no
C8 N4 C14 C9 . -0.9(4) no
C8 N4 C14 C13 . 176.6(5) no
C9 N3 C8 N4 . -1.0(5) no
C9 C10 C11 C12 . 0.5(8) no
C10 C9 C14 N4 . 178.9(4) no
C10 C9 C14 C13 . 1.0(6) no
C10 C11 C12 C13 . 0.5(9) no
C11 C12 C13 C14 . -0.7(8) no
C12 C13 C14 N4 . -177.2(5) no
C12 C13 C14 C9 . 0.0(7) no
C14 N4 C8 N3 . 1.2(5) no
C14 C9 C10 C11 . -1.2(7) no
C16 O3 C17 C18 . 0.3(6) no
C16 O3 C17 C22 . -178.7(3) no
C17 O3 C16 C15 . -73.2(5) no
C17 C18 C19 C20 . -0.4(7) no
C18 C17 C22 C21 . 1.3(6) no
C18 C19 C20 C21 . 2.4(7) no
C19 C20 C21 C22 . -2.6(6) no
C19 C20 C21 C23 . 178.9(4) no
C20 C21 C22 C17 . 0.7(6) no
C20 C21 C23 O4 . 0.2(6) no
C20 C21 C23 O5 . 178.3(4) no
C22 C17 C18 C19 . -1.5(6) no
C22 C21 C23 O4 . -178.4(4) no
C22 C21 C23 O5 . -0.3(6) no
C23 C21 C22 C17 . 179.4(4) no
