#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/02/2210251.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_2210251
loop_
_publ_author_name
'Xuan Huang'
'Li-Ping Xiao'
'Duan-Jun Xu'
_publ_section_title
;
 Bis(benzimidazole-κN)bis(3,5-dihydroxybenzoato-κO)copper(II)
 trihydrate
;
_journal_coeditor_code           HB2116
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2246
_journal_page_last               m2248
_journal_paper_doi               10.1107/S1600536806032417
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu (C7 H5 O4)2 (C7 H6 N2)2], 3H2 O'
_chemical_formula_moiety         'C28 H22 Cu N4 O8, 3H2 O'
_chemical_formula_sum            'C28 H28 Cu N4 O11'
_chemical_formula_weight         660.08
_chemical_name_systematic
;
Bis(benzimidazole-\kN)bis(3,5-dihydroxybenzoato-\kO)copper(II)
trihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.605(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.313(5)
_cell_length_b                   9.740(2)
_cell_length_c                   17.838(5)
_cell_measurement_reflns_used    16422
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.2
_cell_volume                     2809.3(13)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_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     0.71075
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_sigmaI/netI    0.042
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26824
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1364
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.51
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.065
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²+1.3478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.105
_reflns_number_gt                4732
_reflns_number_total             6430
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2116.cif
_cod_data_source_block           I
_cod_original_cell_volume        2809.4(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2210251
_cod_database_fobs_code          2210251
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_refinement_flags
_atom_site_occupancy
Cu Cu 0.523352(16) 0.23846(3) 0.728768(17) 0.02705(9) Uani d . 1
O O1 0.64223(9) 0.21813(17) 0.75022(10) 0.0323(4) Uani d . 1
O O2 0.63678(10) 0.02912(17) 0.81960(10) 0.0348(4) Uani d . 1
O O3 0.93650(10) -0.09567(17) 0.89023(10) 0.0371(4) Uani d . 1
H H3 0.9907 -0.0880 0.8979 0.056 Uiso d R 1
O O4 0.94352(10) 0.30999(17) 0.74467(10) 0.0332(4) Uani d . 1
H H4 0.9127 0.3865 0.7181 0.050 Uiso d R 1
O O5 0.40469(10) 0.26706(18) 0.70583(10) 0.0357(4) Uani d . 1
O O6 0.40430(10) 0.41995(19) 0.61298(11) 0.0385(4) Uani d . 1
O O7 0.11162(12) 0.5796(2) 0.56279(13) 0.0568(6) Uani d . 1
H H7 0.0610 0.5945 0.5742 0.085 Uiso d R 1
O O8 0.11454(12) 0.2475(2) 0.76162(12) 0.0518(5) Uani d . 1
H H8 0.0599 0.2537 0.7509 0.078 Uiso d R 1
N N31 0.51434(12) 0.08665(19) 0.65349(12) 0.0294(4) Uani d . 1
N N33 0.45771(13) -0.0984(2) 0.59546(12) 0.0356(5) Uani d . 1
H H33 0.4215 -0.1605 0.5812 0.043 Uiso calc R 1
N N41 0.53075(12) 0.3764(2) 0.81251(12) 0.0321(5) Uani d . 1
N N43 0.58761(14) 0.5522(2) 0.87933(12) 0.0389(5) Uani d . 1
H H43 0.6245 0.6104 0.8979 0.047 Uiso calc R 1
C C11 0.76880(13) 0.1190(2) 0.80193(13) 0.0241(5) Uani d . 1
C C12 0.81087(14) 0.0147(2) 0.84402(13) 0.0268(5) Uani d . 1
H H12 0.7820 -0.0523 0.8668 0.032 Uiso calc R 1
C C13 0.89640(14) 0.0121(2) 0.85153(13) 0.0263(5) Uani d . 1
C C14 0.93993(14) 0.1118(2) 0.81898(13) 0.0266(5) Uani d . 1
H H14 0.9974 0.1095 0.8249 0.032 Uiso calc R 1
C C15 0.89723(14) 0.2160(2) 0.77721(13) 0.0256(5) Uani d . 1
C C16 0.81150(14) 0.2207(2) 0.76868(14) 0.0264(5) Uani d . 1
H H16 0.7831 0.2910 0.7411 0.032 Uiso calc R 1
C C17 0.67608(14) 0.1203(2) 0.79039(13) 0.0269(5) Uani d . 1
C C21 0.27723(14) 0.3700(2) 0.65894(14) 0.0303(5) Uani d . 1
C C22 0.23475(15) 0.4643(3) 0.61048(16) 0.0386(6) Uani d . 1
H H22 0.2621 0.5119 0.5760 0.046 Uiso calc R 1
C C23 0.15182(15) 0.4877(3) 0.61338(15) 0.0366(6) Uani d . 1
C C24 0.11065(15) 0.4177(3) 0.66457(15) 0.0356(6) Uani d . 1
H H24 0.0551 0.4355 0.6674 0.043 Uiso calc R 1
C C25 0.15299(15) 0.3210(3) 0.71149(15) 0.0347(6) Uani d . 1
C C26 0.23621(14) 0.2964(3) 0.70876(15) 0.0333(5) Uani d . 1
H H26 0.2643 0.2308 0.7402 0.040 Uiso calc R 1
C C27 0.36874(14) 0.3519(2) 0.65853(14) 0.0301(5) Uani d . 1
C C32 0.44767(15) 0.0082(3) 0.64041(14) 0.0334(6) Uani d . 1
H H32 0.3989 0.0255 0.6605 0.040 Uiso calc R 1
C C34 0.53641(16) -0.0911(2) 0.57598(14) 0.0321(5) Uani d . 1
C C35 0.57805(18) -0.1762(3) 0.53173(15) 0.0408(6) Uani d . 1
H H35 0.5534 -0.2542 0.5086 0.049 Uiso calc R 1
C C36 0.65745(18) -0.1396(3) 0.52377(16) 0.0453(7) Uani d . 1
H H36 0.6880 -0.1947 0.4951 0.054 Uiso calc R 1
C C37 0.69352(17) -0.0213(3) 0.55772(16) 0.0441(7) Uani d . 1
H H37 0.7471 0.0015 0.5500 0.053 Uiso calc R 1
C C38 0.65220(16) 0.0630(3) 0.60235(15) 0.0362(6) Uani d . 1
H H38 0.6769 0.1415 0.6248 0.043 Uiso calc R 1
C C39 0.57236(15) 0.0256(2) 0.61231(14) 0.0300(5) Uani d . 1
C C42 0.59862(16) 0.4501(3) 0.83210(14) 0.0348(6) Uani d . 1
H H42 0.6488 0.4322 0.8146 0.042 Uiso calc R 1
C C44 0.50637(17) 0.5482(3) 0.89323(14) 0.0383(6) Uani d . 1
C C45 0.4638(2) 0.6299(3) 0.93876(17) 0.0512(8) Uani d . 1
H H45 0.4888 0.7035 0.9660 0.061 Uiso calc R 1
C C46 0.3832(2) 0.5959(4) 0.94130(18) 0.0618(10) Uani d . 1
H H46 0.3518 0.6488 0.9703 0.074 Uiso calc R 1
C C47 0.3466(2) 0.4839(4) 0.90144(18) 0.0593(9) Uani d . 1
H H47 0.2917 0.4633 0.9053 0.071 Uiso calc R 1
C C48 0.38901(18) 0.4023(3) 0.85641(16) 0.0485(7) Uani d . 1
H H48 0.3641 0.3274 0.8303 0.058 Uiso calc R 1
C C49 0.47086(16) 0.4374(3) 0.85178(14) 0.0347(6) Uani d . 1
O O1W 0.81032(18) 0.2677(3) 0.54857(18) 0.0909(10) Uani d . 1
H H1A 0.8270 0.3205 0.5130 0.136 Uiso d R 1
H H1B 0.7535 0.2637 0.5293 0.136 Uiso d R 1
O O2W 0.62801(13) 0.3305(2) 0.47268(12) 0.0493(5) Uani d . 1
H H2A 0.6189 0.4136 0.4479 0.074 Uiso d R 1
H H2B 0.6043 0.3554 0.5147 0.074 Uiso d R 1
O O3W -0.04935(13) 0.6018(3) 0.56466(12) 0.0622(6) Uani d . 1
H H3A -0.0833 0.5430 0.5288 0.093 Uiso d R 1
H H3B -0.0783 0.5827 0.6072 0.093 Uiso d R 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'
Cu Cu 0.3201 1.2651 '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_publ_flag
O1 Cu O5 177.50(7) y
O1 Cu N31 92.29(7) y
O5 Cu N31 88.96(8) y
O1 Cu N41 87.78(8) y
O5 Cu N41 91.19(8) y
N31 Cu N41 174.07(8) y
C17 O1 Cu 122.41(15) ?
C13 O3 H3 114.5 ?
C15 O4 H4 115.9 ?
C27 O5 Cu 126.38(16) ?
C23 O7 H7 109.5 ?
C25 O8 H8 111.0 ?
C32 N31 C39 104.9(2) ?
C32 N31 Cu 122.23(18) ?
C39 N31 Cu 132.29(16) ?
C32 N33 C34 107.7(2) ?
C32 N33 H33 126.1 ?
C34 N33 H33 126.1 ?
C42 N41 C49 104.5(2) ?
C42 N41 Cu 121.71(17) ?
C49 N41 Cu 132.69(17) ?
C42 N43 C44 107.8(2) ?
C42 N43 H43 126.1 ?
C44 N43 H43 126.1 ?
C12 C11 C16 120.8(2) ?
C12 C11 C17 119.9(2) ?
C16 C11 C17 119.3(2) ?
C13 C12 C11 119.1(2) ?
C13 C12 H12 120.5 ?
C11 C12 H12 120.5 ?
O3 C13 C14 120.9(2) ?
O3 C13 C12 118.0(2) ?
C14 C13 C12 121.1(2) ?
C13 C14 C15 119.4(2) ?
C13 C14 H14 120.3 ?
C15 C14 H14 120.3 ?
O4 C15 C16 122.5(2) ?
O4 C15 C14 116.8(2) ?
C16 C15 C14 120.6(2) ?
C15 C16 C11 119.0(2) ?
C15 C16 H16 120.5 ?
C11 C16 H16 120.5 ?
O2 C17 O1 123.9(2) ?
O2 C17 C11 120.1(2) ?
O1 C17 C11 116.0(2) ?
C26 C21 C22 120.1(2) ?
C26 C21 C27 120.5(2) ?
C22 C21 C27 119.4(2) ?
C23 C22 C21 119.9(2) ?
C23 C22 H22 120.0 ?
C21 C22 H22 120.0 ?
O7 C23 C22 117.9(2) ?
O7 C23 C24 121.6(2) ?
C22 C23 C24 120.5(2) ?
C23 C24 C25 119.2(2) ?
C23 C24 H24 120.4 ?
C25 C24 H24 120.4 ?
O8 C25 C24 121.3(2) ?
O8 C25 C26 118.1(2) ?
C24 C25 C26 120.6(2) ?
C21 C26 C25 119.6(2) ?
C21 C26 H26 120.2 ?
C25 C26 H26 120.2 ?
O6 C27 O5 124.4(2) ?
O6 C27 C21 119.2(2) ?
O5 C27 C21 116.4(2) ?
N31 C32 N33 113.0(2) ?
N31 C32 H32 123.5 ?
N33 C32 H32 123.5 ?
N33 C34 C35 131.2(2) ?
N33 C34 C39 105.9(2) ?
C35 C34 C39 123.0(3) ?
C36 C35 C34 116.5(3) ?
C36 C35 H35 121.8 ?
C34 C35 H35 121.8 ?
C35 C36 C37 121.4(3) ?
C35 C36 H36 119.3 ?
C37 C36 H36 119.3 ?
C38 C37 C36 122.1(3) ?
C38 C37 H37 118.9 ?
C36 C37 H37 118.9 ?
C37 C38 C39 117.2(2) ?
C37 C38 H38 121.4 ?
C39 C38 H38 121.4 ?
C38 C39 C34 119.8(2) ?
C38 C39 N31 131.7(2) ?
C34 C39 N31 108.4(2) ?
N41 C42 N43 113.2(2) ?
N41 C42 H42 123.4 ?
N43 C42 H42 123.4 ?
N43 C44 C45 131.0(3) ?
N43 C44 C49 105.6(2) ?
C45 C44 C49 123.4(3) ?
C46 C45 C44 116.2(3) ?
C46 C45 H45 121.9 ?
C44 C45 H45 121.9 ?
C45 C46 C47 121.5(3) ?
C45 C46 H46 119.2 ?
C47 C46 H46 119.2 ?
C48 C47 C46 122.3(3) ?
C48 C47 H47 118.8 ?
C46 C47 H47 118.8 ?
C47 C48 C49 116.9(3) ?
C47 C48 H48 121.5 ?
C49 C48 H48 121.5 ?
C44 C49 C48 119.6(3) ?
C44 C49 N41 108.9(2) ?
C48 C49 N41 131.4(3) ?
H1A O1W H1B 98.1 ?
H2A O2W H2B 95.8 ?
H3A O3W H3B 96.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu O1 1.9365(17) y
Cu O5 1.9449(17) y
Cu N31 1.990(2) y
Cu N41 2.001(2) y
C17 O1 1.274(3) y
C17 O2 1.249(3) y
C27 O5 1.268(3) y
C27 O6 1.249(3) y
O3 C13 1.373(3) ?
O3 H3 0.8804 ?
O4 C15 1.364(3) ?
O4 H4 0.9841 ?
O7 C23 1.374(3) ?
O7 H7 0.8890 ?
O8 C25 1.361(3) ?
O8 H8 0.8889 ?
N31 C32 1.325(3) ?
N31 C39 1.405(3) ?
N33 C32 1.335(3) ?
N33 C34 1.375(3) ?
N33 H33 0.8600 ?
N41 C42 1.327(3) ?
N41 C49 1.407(3) ?
N43 C42 1.331(3) ?
N43 C44 1.381(3) ?
N43 H43 0.8600 ?
C11 C12 1.389(3) ?
C11 C16 1.389(3) ?
C11 C17 1.499(3) ?
C12 C13 1.384(3) ?
C12 H12 0.9300 ?
C13 C14 1.376(3) ?
C14 C15 1.390(3) ?
C14 H14 0.9300 ?
C15 C16 1.388(3) ?
C16 H16 0.9300 ?
C21 C26 1.382(4) ?
C21 C22 1.383(4) ?
C21 C27 1.504(3) ?
C22 C23 1.380(3) ?
C22 H22 0.9300 ?
C23 C24 1.383(4) ?
C24 C25 1.383(4) ?
C24 H24 0.9300 ?
C25 C26 1.386(3) ?
C26 H26 0.9300 ?
C32 H32 0.9300 ?
C34 C35 1.383(4) ?
C34 C39 1.398(3) ?
C35 C36 1.369(4) ?
C35 H35 0.9300 ?
C36 C37 1.395(4) ?
C36 H36 0.9300 ?
C37 C38 1.380(4) ?
C37 H37 0.9300 ?
C38 C39 1.386(3) ?
C38 H38 0.9300 ?
C42 H42 0.9300 ?
C44 C45 1.388(4) ?
C44 C49 1.390(4) ?
C45 C46 1.362(5) ?
C45 H45 0.9300 ?
C46 C47 1.393(5) ?
C46 H46 0.9300 ?
C47 C48 1.379(4) ?
C47 H47 0.9300 ?
C48 C49 1.391(4) ?
C48 H48 0.9300 ?
O1W H1A 0.8873 ?
O1W H1B 0.9458 ?
O2W H2A 0.9250 ?
O2W H2B 0.9195 ?
O3W H3A 0.9747 ?
O3W H3B 0.9634 ?
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
N33 H33 O2W 3_656 0.86 2.03 2.845(3) 158 y
N43 H43 O1W 2_656 0.86 2.03 2.875(4) 167 y
O3 H3 O6 2_646 0.88 1.75 2.610(2) 165 y
O4 H4 O2 2_656 0.98 1.70 2.681(3) 174 y
O7 H7 O3W . 0.89 1.79 2.639(3) 160 y
O8 H8 O4 1_455 0.89 1.97 2.832(3) 165 y
O1W H1A O7 3_666 0.89 2.03 2.907(4) 168 y
O1W H1B O2W . 0.95 2.26 3.160(4) 160 y
O2W H2A O6 3_666 0.92 1.96 2.882(3) 175 y
O2W H2B O3 2_656 0.92 1.96 2.878(3) 175 y
O3W H3A O7 3_566 0.97 2.03 2.951(3) 158 y
O3W H3B O2 2_556 0.96 1.79 2.753(3) 173 y
