#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/33/2223320.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_2223320
loop_
_publ_author_name
'Cai, Ying'
_publ_section_title
;(1R,2S,3R,5S)-5-(1H-Benzimidazol-2-yl)cyclohexane-1,2,3,5-tetraol
 monohydrate
;
_journal_coeditor_code           BX2237
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2547
_journal_paper_doi               10.1107/S1600536809037957
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H16 N2 O4, H2 O'
_chemical_formula_moiety         'C13 H16 N2 O4, H2 O'
_chemical_formula_sum            'C13 H18 N2 O5'
_chemical_formula_weight         282.29
_chemical_name_systematic
;
(1R,2S,3R,5S)-5-(1H-Benzimidazol-2-
yl)cyclohexane-1,2,3,5-tetraol monohydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9684(14)
_cell_length_b                   9.4809(15)
_cell_length_c                   15.278(4)
_cell_measurement_reflns_used    3450
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.56
_cell_volume                     1299.1(4)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12121
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9060
_exptl_absorpt_correction_T_min  0.8172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.181
_refine_ls_extinction_coef       0.0476(15)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         1716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.2437P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0786
_reflns_number_gt                1646
_reflns_number_total             1716
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2237.cif
_cod_data_source_block           I
_cod_original_cell_volume        1299.0(4)
_cod_database_code               2223320
_cod_database_fobs_code          2223320
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O5 0.72771(16) 0.24370(18) 0.64625(9) 0.0354(3) Uani d . 1 . .
C C11 0.6615(2) 0.3526(2) 0.86815(13) 0.0301(4) Uani d . 1 . .
O O3 0.07767(15) 0.25080(16) 0.51676(10) 0.0348(3) Uani d . 1 . .
O O1 0.31588(16) 0.45480(17) 0.50248(9) 0.0356(3) Uani d . 1 . .
N N1 0.57765(19) 0.33374(19) 0.79210(11) 0.0348(4) Uani d . 1 . .
N N2 0.43215(18) 0.42648(18) 0.89530(10) 0.0292(3) Uani d . 1 . .
O O2 0.01088(17) 0.3204(2) 0.69454(10) 0.0435(4) Uani d . 1 . .
C C1 0.1920(2) 0.2640(2) 0.58171(12) 0.0276(4) Uani d . 1 . .
C C2 0.4434(2) 0.3787(2) 0.81175(12) 0.0286(4) Uani d . 1 . .
C C3 0.3703(2) 0.4282(2) 0.65804(12) 0.0280(4) Uani d . 1 . .
C C4 0.5722(2) 0.41153(19) 0.93338(12) 0.0264(4) Uani d . 1 . .
C C5 0.2540(2) 0.4136(2) 0.58515(11) 0.0258(4) Uani d . 1 . .
C C6 0.3142(2) 0.3786(2) 0.74770(12) 0.0266(4) Uani d . 1 . .
C C7 0.2462(3) 0.2298(2) 0.74082(13) 0.0347(4) Uani d . 1 . .
C C8 0.6284(2) 0.4454(2) 1.01561(13) 0.0332(4) Uani d . 1 . .
C C9 0.8684(2) 0.3580(2) 0.96474(15) 0.0368(5) Uani d . 1 . .
C C10 0.7779(2) 0.4184(2) 1.02923(14) 0.0351(4) Uani d . 1 . .
C C12 0.8121(2) 0.3239(2) 0.88366(15) 0.0371(5) Uani d . 1 . .
C C13 0.1264(2) 0.2240(2) 0.66954(13) 0.0340(4) Uani d . 1 . .
O O4 0.20679(15) 0.47505(16) 0.78330(10) 0.0363(3) Uani d . 1 . .
H H1 0.272(2) 0.196(2) 0.5665(14) 0.029(5) Uiso d . 1 . .
H H2 0.328(3) 0.161(3) 0.7259(17) 0.045(7) Uiso d . 1 . .
H H3 0.456(3) 0.376(2) 0.6402(15) 0.033(6) Uiso d . 1 . .
H H4 0.976(3) 0.341(2) 0.9775(15) 0.038(6) Uiso d . 1 . .
H H5 0.173(3) 0.477(2) 0.5973(13) 0.026(5) Uiso d . 1 . .
H H6 0.347(3) 0.459(3) 0.9186(16) 0.042(7) Uiso d . 1 . .
H H7 0.824(3) 0.440(3) 1.0846(16) 0.041(6) Uiso d . 1 . .
H H8 0.875(3) 0.290(3) 0.8364(19) 0.061(8) Uiso d . 1 . .
H H9 0.198(3) 0.206(3) 0.8007(16) 0.042(6) Uiso d . 1 . .
H H10 0.401(3) 0.527(3) 0.6663(15) 0.043(7) Uiso d . 1 . .
H H11 0.567(3) 0.488(3) 1.0588(18) 0.045(7) Uiso d . 1 . .
H H12 0.126(3) 0.252(3) 0.4704(19) 0.058(9) Uiso d . 1 . .
H H13 0.119(3) 0.445(3) 0.7643(18) 0.054(8) Uiso d . 1 . .
H H14 -0.069(3) 0.299(3) 0.6691(18) 0.055(8) Uiso d . 1 . .
H H15 0.393(3) 0.403(3) 0.4937(18) 0.055(8) Uiso d . 1 . .
H H16 0.088(3) 0.123(2) 0.6650(14) 0.029(6) Uiso d . 1 . .
H H17 0.745(4) 0.156(4) 0.661(2) 0.074(10) Uiso d . 1 . .
H H18 0.673(4) 0.272(4) 0.695(2) 0.077(10) Uiso d . 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
H17 O5 H18 . . 99(3) ?
C4 C11 N1 . . 109.71(16) ?
C4 C11 C12 . . 120.72(19) ?
N1 C11 C12 . . 129.55(19) ?
C1 O3 H12 . . 102.6(19) ?
C5 O1 H15 . . 107.0(19) ?
C2 N1 C11 . . 105.19(16) ?
C2 N2 C4 . . 106.96(16) ?
C2 N2 H6 . . 123.3(16) ?
C4 N2 H6 . . 129.7(16) ?
C13 O2 H14 . . 110(2) ?
O3 C1 C13 . . 108.30(15) ?
O3 C1 C5 . . 111.52(15) ?
C13 C1 C5 . . 110.17(15) ?
O3 C1 H1 . . 107.5(12) ?
C13 C1 H1 . . 109.1(12) ?
C5 C1 H1 . . 110.2(12) ?
N1 C2 N2 . . 113.06(17) ?
N1 C2 C6 . . 123.58(17) ?
N2 C2 C6 . . 123.37(16) ?
C5 C3 C6 . . 113.48(15) ?
C5 C3 H3 . . 107.0(14) ?
C6 C3 H3 . . 111.0(14) ?
C5 C3 H10 . . 111.7(14) ?
C6 C3 H10 . . 105.6(14) ?
H3 C3 H10 . . 107.9(19) ?
C8 C4 N2 . . 132.89(18) ?
C8 C4 C11 . . 122.02(17) ?
N2 C4 C11 . . 105.07(16) ?
O1 C5 C1 . . 111.36(15) ?
O1 C5 C3 . . 110.63(14) ?
C1 C5 C3 . . 110.96(15) ?
O1 C5 H5 . . 107.1(12) ?
C1 C5 H5 . . 108.0(13) ?
C3 C5 H5 . . 108.7(12) ?
O4 C6 C2 . . 105.52(14) ?
O4 C6 C3 . . 111.29(16) ?
C2 C6 C3 . . 109.00(15) ?
O4 C6 C7 . . 110.09(16) ?
C2 C6 C7 . . 110.33(15) ?
C3 C6 C7 . . 110.49(15) ?
C13 C7 C6 . . 111.08(16) ?
C13 C7 H2 . . 109.1(15) ?
C6 C7 H2 . . 108.6(15) ?
C13 C7 H9 . . 109.1(15) ?
C6 C7 H9 . . 107.7(13) ?
H2 C7 H9 . . 111(2) ?
C10 C8 C4 . . 116.39(19) ?
C10 C8 H11 . . 122.5(16) ?
C4 C8 H11 . . 121.1(16) ?
C12 C9 C10 . . 121.11(19) ?
C12 C9 H4 . . 119.5(14) ?
C10 C9 H4 . . 119.4(14) ?
C8 C10 C9 . . 122.24(19) ?
C8 C10 H7 . . 120.5(16) ?
C9 C10 H7 . . 117.3(16) ?
C9 C12 C11 . . 117.5(2) ?
C9 C12 H8 . . 122.3(17) ?
C11 C12 H8 . . 120.0(17) ?
O2 C13 C1 . . 110.91(17) ?
O2 C13 C7 . . 107.13(16) ?
C1 C13 C7 . . 110.40(16) ?
O2 C13 H16 . . 111.8(13) ?
C1 C13 H16 . . 107.9(13) ?
C7 C13 H16 . . 108.7(13) ?
C6 O4 H13 . . 105.7(18) ?
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
O5 H17 . 0.88(3) ?
O5 H18 . 0.93(4) ?
C11 C4 . 1.395(3) ?
C11 N1 . 1.395(2) ?
C11 C12 . 1.398(3) ?
O3 C1 . 1.432(2) ?
O3 H12 . 0.83(3) ?
O1 C5 . 1.434(2) ?
O1 H15 . 0.86(3) ?
N1 C2 . 1.312(2) ?
N2 C2 . 1.358(2) ?
N2 C4 . 1.392(2) ?
N2 H6 . 0.90(3) ?
O2 C13 . 1.434(3) ?
O2 H14 . 0.84(3) ?
C1 C13 . 1.514(3) ?
C1 C5 . 1.524(3) ?
C1 H1 . 0.99(2) ?
C2 C6 . 1.517(3) ?
C3 C5 . 1.532(2) ?
C3 C6 . 1.533(3) ?
C3 H3 . 0.95(2) ?
C3 H10 . 0.98(3) ?
C4 C8 . 1.391(3) ?
C5 H5 . 0.96(2) ?
C6 O4 . 1.435(2) ?
C6 C7 . 1.540(3) ?
C7 C13 . 1.531(3) ?
C7 H2 . 1.01(3) ?
C7 H9 . 1.04(2) ?
C8 C10 . 1.381(3) ?
C8 H11 . 0.95(3) ?
C9 C12 . 1.376(3) ?
C9 C10 . 1.399(3) ?
C9 H4 . 1.00(2) ?
C10 H7 . 0.96(2) ?
C12 H8 . 0.97(3) ?
C13 H16 . 1.02(2) ?
O4 H13 . 0.89(3) ?
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
N2 H6 O1 2_565 0.90(3) 2.11(3) 2.983(2) 164(2)
O3 H12 O5 4_456 0.83(3) 2.00(3) 2.831(2) 176(3)
O4 H13 O2 . 0.89(3) 1.87(3) 2.660(2) 148(3)
O2 H14 O5 1_455 0.84(3) 1.93(3) 2.743(2) 163(3)
O1 H15 O3 4_556 0.86(3) 2.21(3) 3.066(2) 172(3)
O5 H17 O4 3_646 0.88(3) 1.96(4) 2.827(2) 169(3)
O5 H18 N1 . 0.93(4) 1.81(4) 2.740(2) 176(3)
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 C11 N1 C2 . . . . -0.5(2) ?
C12 C11 N1 C2 . . . . -179.1(2) ?
C11 N1 C2 N2 . . . . 0.2(2) ?
C11 N1 C2 C6 . . . . 179.75(17) ?
C4 N2 C2 N1 . . . . 0.2(2) ?
C4 N2 C2 C6 . . . . -179.36(17) ?
C2 N2 C4 C8 . . . . 178.1(2) ?
C2 N2 C4 C11 . . . . -0.5(2) ?
N1 C11 C4 C8 . . . . -178.15(18) ?
C12 C11 C4 C8 . . . . 0.6(3) ?
N1 C11 C4 N2 . . . . 0.6(2) ?
C12 C11 C4 N2 . . . . 179.4(2) ?
O3 C1 C5 O1 . . . . -59.24(19) ?
C13 C1 C5 O1 . . . . -179.53(15) ?
O3 C1 C5 C3 . . . . 177.05(15) ?
C13 C1 C5 C3 . . . . 56.76(19) ?
C6 C3 C5 O1 . . . . -177.00(16) ?
C6 C3 C5 C1 . . . . -52.9(2) ?
N1 C2 C6 O4 . . . . -161.58(19) ?
N2 C2 C6 O4 . . . . 17.9(2) ?
N1 C2 C6 C3 . . . . -42.0(3) ?
N2 C2 C6 C3 . . . . 137.55(19) ?
N1 C2 C6 C7 . . . . 79.5(2) ?
N2 C2 C6 C7 . . . . -101.0(2) ?
C5 C3 C6 O4 . . . . -71.7(2) ?
C5 C3 C6 C2 . . . . 172.34(15) ?
C5 C3 C6 C7 . . . . 50.9(2) ?
O4 C6 C7 C13 . . . . 69.8(2) ?
C2 C6 C7 C13 . . . . -174.09(16) ?
C3 C6 C7 C13 . . . . -53.5(2) ?
N2 C4 C8 C10 . . . . -178.0(2) ?
C11 C4 C8 C10 . . . . 0.4(3) ?
C4 C8 C10 C9 . . . . -1.0(3) ?
C12 C9 C10 C8 . . . . 0.7(3) ?
C10 C9 C12 C11 . . . . 0.3(3) ?
C4 C11 C12 C9 . . . . -0.9(3) ?
N1 C11 C12 C9 . . . . 177.6(2) ?
O3 C1 C13 O2 . . . . -64.01(19) ?
C5 C1 C13 O2 . . . . 58.20(19) ?
O3 C1 C13 C7 . . . . 177.41(16) ?
C5 C1 C13 C7 . . . . -60.4(2) ?
C6 C7 C13 O2 . . . . -61.7(2) ?
C6 C7 C13 C1 . . . . 59.1(2) ?
