##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2012-05-18
_journal_date_accepted     2012-05-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      7
_journal_page_first     o1995
_journal_page_last     o1995
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812023884
_journal_coeditor_code     RZ2764
_publ_contact_author_name     'Abd Hamid, Shafida'
_publ_contact_author_address
;
 Kulliyah of Science, International Islamic University Malaysia
 Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia.
;
_publ_contact_author_email     'shafida@iium.edu.my'
_publ_contact_author_fax     '6 09 5716781'
_publ_contact_author_phone     '6 09 5716400'
_publ_section_title
;
2-sec-Butyl-1-(2-hydroxyethyl)-1H-benzimidazole-5-carboxylic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hamzah, Nurasyikin' ?
;     Kulliyyah of Science, International Islamic University Malaysia
      Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia
            School of Pharmaceutical Sciences,
       Universiti Sains Malaysia, 11800 Penang, Malaysia
;
    'Ngah, Nurziana' ?
;     Kulliyyah of Science, International Islamic University Malaysia
      Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia
;
    'Abd Hamid, Shafida' ?
;     Kulliyyah of Science, International Islamic University Malaysia
      Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia
;
    'Abdul Rahim, Aisyah Saad' ?
;      School of Pharmaceutical Sciences,
       Universiti Sains Malaysia, 11800 Penang, Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-sec-Butyl-1-(2-hydroxyethyl)-1H-benzimidazole-5-carboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H18 N2 O3'
_chemical_formula_sum     'C14 H18 N2 O3'
_chemical_formula_iupac     'C14 H18 N2 O3'
_chemical_formula_weight     262.30
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     8.9427(2)
_cell_length_b     8.2067(2)
_cell_length_c     18.3536(3)
_cell_angle_alpha     90.00
_cell_angle_beta     94.4150(10)
_cell_angle_gamma     90.00
_cell_volume     1342.97(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6388
_cell_measurement_theta_min     2.4
_cell_measurement_theta_max     25.5
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.36
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.297
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     560
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9554
_exptl_absorpt_correction_T_max     0.9859
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems Cobra
open=flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0(1) K.
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method     'φ and ω scan'
_diffrn_detector_area_resol_mean     83.66
_diffrn_reflns_number     11481
_diffrn_reflns_av_R_equivalents     0.0207
_diffrn_reflns_av_sigmaI/netI     0.0166
_diffrn_reflns_theta_min     2.4
_diffrn_reflns_theta_max     25.5
_diffrn_reflns_theta_full     25.5
_diffrn_measured_fraction_theta_max     1.00
_diffrn_measured_fraction_theta_full     1.00
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2491
_reflns_number_gt     2190
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0387
_refine_ls_R_factor_gt     0.0337
_refine_ls_wR_factor_gt     0.0837
_refine_ls_wR_factor_ref     0.0876
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.028
_refine_ls_number_reflns     2491
_refine_ls_number_parameters     200
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0428P)²+0.5356P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.20
_refine_diff_density_min     -0.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT  (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 -0.34306(10) 0.27634(12) 0.46443(5) 0.0256(2) Uani d . 1 1 . .
    O O2 -0.18373(11) 0.07220(12) 0.49284(5) 0.0287(2) Uani d . 1 1 . .
    O O3 0.20151(10) 0.42060(11) 0.12007(5) 0.0219(2) Uani d . 1 1 . .
    N N1 0.12053(11) 0.03383(12) 0.26410(5) 0.0190(2) Uani d . 1 1 . .
    N N2 -0.00305(11) 0.18127(12) 0.17645(5) 0.0180(2) Uani d . 1 1 . .
    C C1 -0.00646(13) 0.10204(14) 0.29170(6) 0.0170(3) Uani d . 1 1 . .
    C C2 -0.05883(13) 0.09255(15) 0.36115(6) 0.0180(3) Uani d . 1 1 . .
    H H2A -0.0087 0.0282 0.3985 0.022 Uiso calc R 1 1 . .
    C C3 -0.18717(13) 0.18066(15) 0.37392(7) 0.0186(3) Uani d . 1 1 . .
    C C4 -0.26332(14) 0.27436(16) 0.31848(7) 0.0211(3) Uani d . 1 1 . .
    H H4A -0.3507 0.3330 0.3290 0.025 Uiso calc R 1 1 . .
    C C5 -0.21368(14) 0.28282(16) 0.24910(7) 0.0214(3) Uani d . 1 1 . .
    H H5A -0.2653 0.3450 0.2114 0.026 Uiso calc R 1 1 . .
    C C6 -0.08397(13) 0.19556(15) 0.23719(6) 0.0176(3) Uani d . 1 1 . .
    C C7 0.11917(13) 0.08457(15) 0.19581(6) 0.0181(3) Uani d . 1 1 A .
    C C8 -0.24608(13) 0.18323(15) 0.44752(7) 0.0194(3) Uani d . 1 1 . .
    C C9 -0.03388(14) 0.27534(16) 0.10911(6) 0.0205(3) Uani d . 1 1 . .
    H H9A -0.1435 0.2911 0.1000 0.025 Uiso calc R 1 1 . .
    H H9B 0.0017 0.2136 0.0674 0.025 Uiso calc R 1 1 . .
    C C10 0.04292(14) 0.44020(16) 0.11404(7) 0.0217(3) Uani d . 1 1 . .
    H H10A 0.0124 0.5050 0.0699 0.026 Uiso calc R 1 1 . .
    H H10B 0.0116 0.5000 0.1572 0.026 Uiso calc R 1 1 . .
    C C11 0.23294(13) 0.03938(15) 0.14321(6) 0.0212(3) Uani d D 1 1 . .
    H H11A 0.2217 0.1164 0.1009 0.025 Uiso calc PR 0.484(4) 1 A 1
    H H11B 0.2149 0.1112 0.0994 0.025 Uiso d PR 0.516(4) 1 A 2
    C C12 0.3911(9) 0.061(4) 0.1808(11) 0.0279(10) Uani d PD 0.484(4) 1 A 1
    H H12A 0.4656 0.0439 0.1451 0.042 Uiso calc PR 0.484(4) 1 A 1
    H H12B 0.4070 -0.0189 0.2204 0.042 Uiso calc PR 0.484(4) 1 A 1
    H H12C 0.4015 0.1712 0.2010 0.042 Uiso calc PR 0.484(4) 1 A 1
    C C13 0.208(3) -0.135(2) 0.1137(10) 0.0288(5) Uani d PD 0.484(4) 1 A 1
    H H13A 0.2441 -0.2149 0.1513 0.035 Uiso calc PR 0.484(4) 1 A 1
    H H13B 0.0998 -0.1539 0.1012 0.035 Uiso calc PR 0.484(4) 1 A 1
    C C14 0.2951(4) -0.1541(4) 0.04528(15) 0.0302(8) Uani d PD 0.484(4) 1 A 1
    H H14A 0.2766 -0.2628 0.0244 0.045 Uiso calc PR 0.484(4) 1 A 1
    H H14B 0.4026 -0.1406 0.0586 0.045 Uiso calc PR 0.484(4) 1 A 1
    H H14C 0.2616 -0.0713 0.0092 0.045 Uiso calc PR 0.484(4) 1 A 1
    C C12X 0.202(2) -0.1350(18) 0.1179(9) 0.0288(5) Uani d PD 0.516(4) 1 A 2
    H H12D 0.2770 -0.1682 0.0847 0.043 Uiso calc PR 0.516(4) 1 A 2
    H H12E 0.1017 -0.1412 0.0924 0.043 Uiso calc PR 0.516(4) 1 A 2
    H H12F 0.2071 -0.2077 0.1604 0.043 Uiso calc PR 0.516(4) 1 A 2
    C C13X 0.3932(8) 0.068(4) 0.1744(10) 0.0279(10) Uani d PD 0.516(4) 1 A 2
    H H13C 0.4247 -0.0221 0.2081 0.033 Uiso calc PR 0.516(4) 1 A 2
    H H13D 0.3986 0.1709 0.2025 0.033 Uiso calc PR 0.516(4) 1 A 2
    C C14X 0.4982(3) 0.0770(3) 0.11315(15) 0.0282(8) Uani d PD 0.516(4) 1 A 2
    H H14D 0.6015 0.0908 0.1341 0.042 Uiso calc PR 0.516(4) 1 A 2
    H H14E 0.4702 0.1698 0.0814 0.042 Uiso calc PR 0.516(4) 1 A 2
    H H14F 0.4905 -0.0238 0.0845 0.042 Uiso calc PR 0.516(4) 1 A 2
    H H3 0.248(2) 0.459(2) 0.1644(11) 0.055(5) Uiso d . 1 1 . .
    H H2 -0.224(2) 0.080(2) 0.5373(11) 0.057(6) Uiso d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    O1 C8 . 1.2140(15) ?
    O2 C8 . 1.3273(16) ?
    O2 H2 . 0.92(2) ?
    O3 C10 . 1.4231(15) ?
    O3 H3 . 0.94(2) ?
    N1 C7 . 1.3199(16) ?
    N1 C1 . 1.3958(15) ?
    N2 C7 . 1.3750(16) ?
    N2 C6 . 1.3799(15) ?
    N2 C9 . 1.4653(15) ?
    C1 C2 . 1.3936(17) ?
    C1 C6 . 1.4013(17) ?
    C2 C3 . 1.3916(17) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.4084(18) ?
    C3 C8 . 1.4873(16) ?
    C4 C5 . 1.3822(17) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.3947(17) ?
    C5 H5A . 0.9500 ?
    C7 C11 . 1.5019(16) ?
    C9 C10 . 1.5169(18) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C13X . 1.520(11) ?
    C11 C12X . 1.523(11) ?
    C11 C12 . 1.535(12) ?
    C11 C13 . 1.537(12) ?
    C11 H11A . 1.0000 ?
    C11 H11B . 1.0000 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 C14 . 1.536(12) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C12X H12D . 0.9800 ?
    C12X H12E . 0.9800 ?
    C12X H12F . 0.9800 ?
    C13X C14X . 1.521(11) ?
    C13X H13C . 0.9900 ?
    C13X H13D . 0.9900 ?
    C14X H14D . 0.9800 ?
    C14X H14E . 0.9800 ?
    C14X H14F . 0.9800 ?
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
    C8 O2 H2 . . 109.3(12) ?
    C10 O3 H3 . . 113.7(12) ?
    C7 N1 C1 . . 105.66(10) ?
    C7 N2 C6 . . 107.23(9) ?
    C7 N2 C9 . . 128.04(10) ?
    C6 N2 C9 . . 124.07(10) ?
    C2 C1 N1 . . 130.52(11) ?
    C2 C1 C6 . . 120.07(11) ?
    N1 C1 C6 . . 109.39(10) ?
    C3 C2 C1 . . 117.68(11) ?
    C3 C2 H2A . . 121.2 ?
    C1 C2 H2A . . 121.2 ?
    C2 C3 C4 . . 121.41(11) ?
    C2 C3 C8 . . 120.98(11) ?
    C4 C3 C8 . . 117.58(11) ?
    C5 C4 C3 . . 121.42(11) ?
    C5 C4 H4A . . 119.3 ?
    C3 C4 H4A . . 119.3 ?
    C4 C5 C6 . . 116.65(11) ?
    C4 C5 H5A . . 121.7 ?
    C6 C5 H5A . . 121.7 ?
    N2 C6 C5 . . 131.64(11) ?
    N2 C6 C1 . . 105.60(10) ?
    C5 C6 C1 . . 122.75(11) ?
    N1 C7 N2 . . 112.11(10) ?
    N1 C7 C11 . . 125.12(11) ?
    N2 C7 C11 . . 122.74(10) ?
    O1 C8 O2 . . 123.08(11) ?
    O1 C8 C3 . . 123.44(11) ?
    O2 C8 C3 . . 113.48(10) ?
    N2 C9 C10 . . 111.39(10) ?
    N2 C9 H9A . . 109.3 ?
    C10 C9 H9A . . 109.3 ?
    N2 C9 H9B . . 109.3 ?
    C10 C9 H9B . . 109.3 ?
    H9A C9 H9B . . 108.0 ?
    O3 C10 C9 . . 110.35(10) ?
    O3 C10 H10A . . 109.6 ?
    C9 C10 H10A . . 109.6 ?
    O3 C10 H10B . . 109.6 ?
    C9 C10 H10B . . 109.6 ?
    H10A C10 H10B . . 108.1 ?
    C7 C11 C13X . . 112.7(7) ?
    C7 C11 C12X . . 108.1(6) ?
    C13X C11 C12X . . 113.8(16) ?
    C7 C11 C12 . . 109.2(7) ?
    C12X C11 C12 . . 112.6(16) ?
    C7 C11 C13 . . 111.6(6) ?
    C13X C11 C13 . . 112.5(15) ?
    C12 C11 C13 . . 111.6(16) ?
    C7 C11 H11A . . 108.1 ?
    C13X C11 H11A . . 103.3 ?
    C12X C11 H11A . . 110.6 ?
    C12 C11 H11A . . 108.1 ?
    C13 C11 H11A . . 108.1 ?
    C7 C11 H11B . . 107.2 ?
    C13X C11 H11B . . 107.5 ?
    C12X C11 H11B . . 107.1 ?
    C12 C11 H11B . . 112.3 ?
    C13 C11 H11B . . 104.7 ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    C14 C13 C11 . . 108.4(12) ?
    C14 C13 H13A . . 110.0 ?
    C11 C13 H13A . . 110.0 ?
    C14 C13 H13B . . 110.0 ?
    C11 C13 H13B . . 110.0 ?
    H13A C13 H13B . . 108.4 ?
    C11 C12X H12D . . 109.5 ?
    C11 C12X H12E . . 109.5 ?
    H12D C12X H12E . . 109.5 ?
    C11 C12X H12F . . 109.5 ?
    H12D C12X H12F . . 109.5 ?
    H12E C12X H12F . . 109.5 ?
    C11 C13X C14X . . 110.3(11) ?
    C11 C13X H13C . . 109.6 ?
    C14X C13X H13C . . 109.6 ?
    C11 C13X H13D . . 109.6 ?
    C14X C13X H13D . . 109.6 ?
    H13C C13X H13D . . 108.1 ?
    C13X C14X H14D . . 109.5 ?
    C13X C14X H14E . . 109.5 ?
    H14D C14X H14E . . 109.5 ?
    C13X C14X H14F . . 109.5 ?
    H14D C14X H14F . . 109.5 ?
    H14E C14X H14F . . 109.5 ?
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
    C7 N1 C1 C2 . . . . -178.32(12) ?
    C7 N1 C1 C6 . . . . 0.04(13) ?
    N1 C1 C2 C3 . . . . 177.08(12) ?
    C6 C1 C2 C3 . . . . -1.13(17) ?
    C1 C2 C3 C4 . . . . 0.97(18) ?
    C1 C2 C3 C8 . . . . -177.09(11) ?
    C2 C3 C4 C5 . . . . -0.06(19) ?
    C8 C3 C4 C5 . . . . 178.06(11) ?
    C3 C4 C5 C6 . . . . -0.67(18) ?
    C7 N2 C6 C5 . . . . 177.59(13) ?
    C9 N2 C6 C5 . . . . 6.3(2) ?
    C7 N2 C6 C1 . . . . -1.03(13) ?
    C9 N2 C6 C1 . . . . -172.36(11) ?
    C4 C5 C6 N2 . . . . -177.92(12) ?
    C4 C5 C6 C1 . . . . 0.50(18) ?
    C2 C1 C6 N2 . . . . 179.18(11) ?
    N1 C1 C6 N2 . . . . 0.62(13) ?
    C2 C1 C6 C5 . . . . 0.41(18) ?
    N1 C1 C6 C5 . . . . -178.15(11) ?
    C1 N1 C7 N2 . . . . -0.72(14) ?
    C1 N1 C7 C11 . . . . -178.65(11) ?
    C6 N2 C7 N1 . . . . 1.13(14) ?
    C9 N2 C7 N1 . . . . 172.02(11) ?
    C6 N2 C7 C11 . . . . 179.12(11) ?
    C9 N2 C7 C11 . . . . -10.00(19) ?
    C2 C3 C8 O1 . . . . 168.54(12) ?
    C4 C3 C8 O1 . . . . -9.59(18) ?
    C2 C3 C8 O2 . . . . -12.30(16) ?
    C4 C3 C8 O2 . . . . 169.57(11) ?
    C7 N2 C9 C10 . . . . -84.32(15) ?
    C6 N2 C9 C10 . . . . 85.16(14) ?
    N2 C9 C10 O3 . . . . 64.65(12) ?
    N1 C7 C11 C13X . . . . -51.4(13) ?
    N2 C7 C11 C13X . . . . 130.8(13) ?
    N1 C7 C11 C12X . . . . 75.2(10) ?
    N2 C7 C11 C12X . . . . -102.5(10) ?
    N1 C7 C11 C12 . . . . -47.6(13) ?
    N2 C7 C11 C12 . . . . 134.7(13) ?
    N1 C7 C11 C13 . . . . 76.3(11) ?
    N2 C7 C11 C13 . . . . -101.4(11) ?
    C7 C11 C13 C14 . . . . 163.5(10) ?
    C13X C11 C13 C14 . . . . -68.6(16) ?
    C12X C11 C13 C14 . . . .  18E1(10)
                                      ?
    C12 C11 C13 C14 . . . . -73.9(18) ?
    C7 C11 C13X C14X . . . . -160.6(13) ?
    C12X C11 C13X C14X . . . . 76(2) ?
    C12 C11 C13X C14X . . . .  15E1(3)
                                      ?
    C13 C11 C13X C14X . . . . 72(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    O2 H2 O3 . . 4_566 0.92(2) 1.71(2) 2.6227(13) 175.8(16) yes
    O3 H3 N1 . . 2_555 0.94(2) 1.801(19) 2.7193(13) 165.1(17) yes
    C9 H9B O1 . . 4_665 0.99 2.43 3.2925(15) 145 yes
    C12X H12E O1 . . 2_445 0.98 2.55 3.517(18) 167 yes
