#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/65/2226590.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_2226590
loop_
_publ_author_name
'Hamzah, Nurasyikin'
'Abd. Hamid, Shafida'
'Abdul Rahim, Aisyah Saad'
'Rosli, Mohd Mustaqim'
'Fun, Hoong-Kun'
_publ_section_title
;
 Ethyl
 1-(2-hydroxyethyl)-2-phenyl-1H-benzimidazole-5-carboxylate
;
_journal_coeditor_code           LH5069
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1824
_journal_page_last               o1825
_journal_paper_doi               10.1107/S1600536810023639
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H18 N2 O3'
_chemical_formula_moiety         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34
_chemical_name_common
;
Ethyl 1-(2-hydroxyethyl)-2-phenyl-1H-benzimidazole-5-carboxylate
;
_chemical_name_systematic
;
Ethyl 1-(2-hydroxyethyl)-2-phenyl-1H-benzimidazole-5-carboxylate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.764(6)
_cell_angle_beta                 107.202(6)
_cell_angle_gamma                102.929(6)
_cell_formula_units_Z            4
_cell_length_a                   8.997(2)
_cell_length_b                   12.988(3)
_cell_length_c                   15.030(3)
_cell_measurement_reflns_used    6508
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      31.10
_cell_measurement_theta_min      2.61
_cell_volume                     1545.5(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34907
_diffrn_reflns_theta_full        31.13
_diffrn_reflns_theta_max         31.13
_diffrn_reflns_theta_min         1.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.397
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         9838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0944P)²+0.2365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                6952
_reflns_number_total             9838
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5069.cif
_cod_data_source_block           I
_cod_database_code               2226590
_cod_database_fobs_code          2226590
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 O1A 1.15213(13) 0.95597(9) 0.66787(8) 0.0189(2) Uani d . 1 . .
O O2A 0.54072(14) 1.15419(10) 0.96176(9) 0.0311(3) Uani d . 1 . .
O O3A 0.78042(13) 1.28774(9) 1.05882(8) 0.0235(2) Uani d . 1 . .
N N1A 1.02010(14) 0.92733(10) 0.82790(8) 0.0147(2) Uani d . 1 . .
N N2A 0.74895(14) 0.84883(10) 0.78666(9) 0.0155(2) Uani d . 1 . .
C C1A 0.96687(16) 1.00752(11) 0.87590(10) 0.0148(2) Uani d . 1 . .
C C2A 1.05169(17) 1.11622(12) 0.94178(10) 0.0171(3) Uani d . 1 . .
H H2AA 1.1641 1.1480 0.9596 0.020 Uiso calc R 1 . .
C C3A 0.95920(17) 1.17389(12) 0.97904(10) 0.0171(3) Uani d . 1 . .
H H3AA 1.0110 1.2462 1.0233 0.021 Uiso calc R 1 . .
C C4A 0.78835(17) 1.12585(12) 0.95159(10) 0.0160(3) Uani d . 1 . .
C C5A 0.70664(17) 1.01725(12) 0.88665(10) 0.0161(3) Uani d . 1 . .
H H5AA 0.5943 0.9853 0.8689 0.019 Uiso calc R 1 . .
C C6A 0.79750(16) 0.95790(12) 0.84909(10) 0.0150(3) Uani d . 1 . .
C C7A 0.88525(16) 0.83316(11) 0.77649(10) 0.0149(3) Uani d . 1 . .
C C8A 0.88701(16) 0.72261(11) 0.72397(10) 0.0161(3) Uani d . 1 . .
C C9A 0.78407(17) 0.62979(12) 0.73233(11) 0.0192(3) Uani d . 1 . .
H H9AA 0.7178 0.6404 0.7686 0.023 Uiso calc R 1 . .
C C10A 0.78010(19) 0.52256(13) 0.68722(12) 0.0219(3) Uani d . 1 . .
H H10A 0.7113 0.4616 0.6931 0.026 Uiso calc R 1 . .
C C11A 0.87878(19) 0.50601(13) 0.63319(12) 0.0234(3) Uani d . 1 . .
H H11A 0.8785 0.4342 0.6043 0.028 Uiso calc R 1 . .
C C12A 0.97797(19) 0.59712(13) 0.62236(12) 0.0235(3) Uani d . 1 . .
H H12A 1.0425 0.5858 0.5850 0.028 Uiso calc R 1 . .
C C13A 0.98171(18) 0.70472(12) 0.66663(11) 0.0195(3) Uani d . 1 . .
H H13A 1.0474 0.7651 0.6582 0.023 Uiso calc R 1 . .
C C14A 1.19033(16) 0.94750(12) 0.83426(10) 0.0170(3) Uani d . 1 . .
H H14A 1.2089 0.8763 0.8138 0.020 Uiso calc R 1 . .
H H14B 1.2633 0.9868 0.9023 0.020 Uiso calc R 1 . .
C C15A 1.23125(17) 1.01573(12) 0.77022(10) 0.0178(3) Uani d . 1 . .
H H15A 1.1993 1.0824 0.7850 0.021 Uiso calc R 1 . .
H H15B 1.3490 1.0392 0.7867 0.021 Uiso calc R 1 . .
C C16A 0.68862(19) 1.18841(12) 0.98976(11) 0.0195(3) Uani d . 1 . .
C C17A 0.6900(2) 1.35453(14) 1.09824(13) 0.0270(3) Uani d . 1 . .
H H17A 0.6001 1.3559 1.0441 0.032 Uiso calc R 1 . .
H H17B 0.7622 1.4307 1.1334 0.032 Uiso calc R 1 . .
C C18A 0.6227(2) 1.30985(16) 1.16688(13) 0.0309(4) Uani d . 1 . .
H H18A 0.5706 1.3591 1.1944 0.046 Uiso calc R 1 . .
H H18B 0.7105 1.3051 1.2190 0.046 Uiso calc R 1 . .
H H18C 0.5438 1.2369 1.1310 0.046 Uiso calc R 1 . .
O O1B 0.44589(13) 0.70587(9) 0.63176(8) 0.0198(2) Uani d . 1 . .
O O2B 0.98042(13) 1.37266(9) 0.85047(9) 0.0261(2) Uani d . 1 . .
O O3B 0.72718(13) 1.37041(9) 0.84618(8) 0.0218(2) Uani d . 1 . .
N N1B 0.56260(14) 0.88812(10) 0.55835(8) 0.0146(2) Uani d . 1 . .
N N2B 0.83526(14) 0.96642(10) 0.60695(9) 0.0159(2) Uani d . 1 . .
C C1B 0.60025(16) 0.99572(11) 0.61970(10) 0.0144(2) Uani d . 1 . .
C C2B 0.50052(16) 1.05442(12) 0.64814(10) 0.0163(3) Uani d . 1 . .
H H2BA 0.3873 1.0224 0.6255 0.020 Uiso calc R 1 . .
C C3B 0.57926(17) 1.16295(12) 0.71190(10) 0.0170(3) Uani d . 1 . .
H H3BA 0.5174 1.2055 0.7320 0.020 Uiso calc R 1 . .
C C4B 0.75098(17) 1.21029(11) 0.74702(10) 0.0158(3) Uani d . 1 . .
C C5B 0.84839(16) 1.15126(11) 0.71697(10) 0.0155(3) Uani d . 1 . .
H H5BA 0.9618 1.1830 0.7404 0.019 Uiso calc R 1 . .
C C6B 0.77088(16) 1.04313(11) 0.65068(10) 0.0146(2) Uani d . 1 . .
C C7B 0.70751(16) 0.87512(11) 0.55223(10) 0.0150(3) Uani d . 1 . .
C C8B 0.72348(17) 0.77623(12) 0.48846(10) 0.0169(3) Uani d . 1 . .
C C9B 0.83211(19) 0.79407(13) 0.43951(12) 0.0235(3) Uani d . 1 . .
H H9BA 0.8894 0.8666 0.4467 0.028 Uiso calc R 1 . .
C C10B 0.8546(2) 0.70370(15) 0.38006(13) 0.0299(4) Uani d . 1 . .
H H10B 0.9284 0.7160 0.3486 0.036 Uiso calc R 1 . .
C C11B 0.7677(2) 0.59535(14) 0.36748(13) 0.0270(3) Uani d . 1 . .
H H11B 0.7813 0.5352 0.3264 0.032 Uiso calc R 1 . .
C C12B 0.66018(19) 0.57676(13) 0.41618(12) 0.0224(3) Uani d . 1 . .
H H12B 0.6027 0.5040 0.4082 0.027 Uiso calc R 1 . .
C C13B 0.63813(17) 0.66645(12) 0.47681(11) 0.0187(3) Uani d . 1 . .
H H13B 0.5666 0.6536 0.5097 0.022 Uiso calc R 1 . .
C C14B 0.39725(16) 0.80879(12) 0.51552(10) 0.0166(3) Uani d . 1 . .
H H14C 0.3917 0.7454 0.4636 0.020 Uiso calc R 1 . .
H H14D 0.3204 0.8442 0.4864 0.020 Uiso calc R 1 . .
C C15B 0.34895(17) 0.76807(12) 0.59306(11) 0.0187(3) Uani d . 1 . .
H H15C 0.3599 0.8320 0.6463 0.022 Uiso calc R 1 . .
H H15D 0.2347 0.7220 0.5639 0.022 Uiso calc R 1 . .
C C16B 0.83472(18) 1.32504(12) 0.81937(10) 0.0179(3) Uani d . 1 . .
C C17B 0.7947(2) 1.48136(13) 0.91805(12) 0.0243(3) Uani d . 1 . .
H H17C 0.8708 1.5301 0.9000 0.029 Uiso calc R 1 . .
H H17D 0.8527 1.4787 0.9827 0.029 Uiso calc R 1 . .
C C18B 0.6526(2) 1.52376(16) 0.91910(15) 0.0354(4) Uani d . 1 . .
H H18D 0.6924 1.5977 0.9659 0.053 Uiso calc R 1 . .
H H18E 0.5786 1.4750 0.9374 0.053 Uiso calc R 1 . .
H H18F 0.5960 1.5256 0.8547 0.053 Uiso calc R 1 . .
H H1OA 1.061(3) 0.9613(18) 0.6519(16) 0.033(6) Uiso d . 1 . .
H H1OB 0.551(3) 0.753(2) 0.6837(18) 0.048(7) 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 0.0016 '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'
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
C15A O1A H1OA . . 106.6(15) ?
C16A O3A C17A . . 115.62(13) ?
C7A N1A C1A . . 106.75(11) ?
C7A N1A C14A . . 130.19(12) ?
C1A N1A C14A . . 123.05(12) ?
C7A N2A C6A . . 105.31(11) ?
N1A C1A C2A . . 131.57(13) ?
N1A C1A C6A . . 105.94(12) ?
C2A C1A C6A . . 122.46(13) ?
C3A C2A C1A . . 116.44(13) ?
C3A C2A H2AA . . 121.8 ?
C1A C2A H2AA . . 121.8 ?
C2A C3A C4A . . 121.80(13) ?
C2A C3A H3AA . . 119.1 ?
C4A C3A H3AA . . 119.1 ?
C5A C4A C3A . . 120.83(13) ?
C5A C4A C16A . . 117.33(13) ?
C3A C4A C16A . . 121.83(13) ?
C6A C5A C4A . . 118.18(13) ?
C6A C5A H5AA . . 120.9 ?
C4A C5A H5AA . . 120.9 ?
N2A C6A C5A . . 130.04(13) ?
N2A C6A C1A . . 109.67(12) ?
C5A C6A C1A . . 120.28(13) ?
N2A C7A N1A . . 112.31(12) ?
N2A C7A C8A . . 121.48(12) ?
N1A C7A C8A . . 125.92(12) ?
C13A C8A C9A . . 118.79(13) ?
C13A C8A C7A . . 124.62(13) ?
C9A C8A C7A . . 116.59(12) ?
C10A C9A C8A . . 120.72(14) ?
C10A C9A H9AA . . 119.6 ?
C8A C9A H9AA . . 119.6 ?
C9A C10A C11A . . 119.98(14) ?
C9A C10A H10A . . 120.0 ?
C11A C10A H10A . . 120.0 ?
C10A C11A C12A . . 119.75(14) ?
C10A C11A H11A . . 120.1 ?
C12A C11A H11A . . 120.1 ?
C13A C12A C11A . . 120.63(14) ?
C13A C12A H12A . . 119.7 ?
C11A C12A H12A . . 119.7 ?
C12A C13A C8A . . 120.08(13) ?
C12A C13A H13A . . 120.0 ?
C8A C13A H13A . . 120.0 ?
N1A C14A C15A . . 112.25(11) ?
N1A C14A H14A . . 109.2 ?
C15A C14A H14A . . 109.2 ?
N1A C14A H14B . . 109.2 ?
C15A C14A H14B . . 109.2 ?
H14A C14A H14B . . 107.9 ?
O1A C15A C14A . . 113.10(12) ?
O1A C15A H15A . . 109.0 ?
C14A C15A H15A . . 109.0 ?
O1A C15A H15B . . 109.0 ?
C14A C15A H15B . . 109.0 ?
H15A C15A H15B . . 107.8 ?
O2A C16A O3A . . 123.39(14) ?
O2A C16A C4A . . 123.88(14) ?
O3A C16A C4A . . 112.73(13) ?
O3A C17A C18A . . 112.42(14) ?
O3A C17A H17A . . 109.1 ?
C18A C17A H17A . . 109.1 ?
O3A C17A H17B . . 109.1 ?
C18A C17A H17B . . 109.1 ?
H17A C17A H17B . . 107.9 ?
C17A C18A H18A . . 109.5 ?
C17A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
C17A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
C15B O1B H1OB . . 112.7(14) ?
C16B O3B C17B . . 116.69(12) ?
C7B N1B C1B . . 106.88(11) ?
C7B N1B C14B . . 130.48(12) ?
C1B N1B C14B . . 122.60(11) ?
C7B N2B C6B . . 105.39(11) ?
N1B C1B C2B . . 131.25(12) ?
N1B C1B C6B . . 105.80(12) ?
C2B C1B C6B . . 122.93(13) ?
C3B C2B C1B . . 116.39(13) ?
C3B C2B H2BA . . 121.8 ?
C1B C2B H2BA . . 121.8 ?
C2B C3B C4B . . 121.44(13) ?
C2B C3B H3BA . . 119.3 ?
C4B C3B H3BA . . 119.3 ?
C5B C4B C3B . . 121.46(13) ?
C5B C4B C16B . . 117.66(12) ?
C3B C4B C16B . . 120.88(13) ?
C4B C5B C6B . . 117.88(12) ?
C4B C5B H5BA . . 121.1 ?
C6B C5B H5BA . . 121.1 ?
N2B C6B C5B . . 130.50(12) ?
N2B C6B C1B . . 109.69(12) ?
C5B C6B C1B . . 119.80(12) ?
N2B C7B N1B . . 112.22(12) ?
N2B C7B C8B . . 122.11(12) ?
N1B C7B C8B . . 125.54(12) ?
C9B C8B C13B . . 119.22(13) ?
C9B C8B C7B . . 117.73(13) ?
C13B C8B C7B . . 123.04(12) ?
C10B C9B C8B . . 120.14(14) ?
C10B C9B H9BA . . 119.9 ?
C8B C9B H9BA . . 119.9 ?
C11B C10B C9B . . 120.35(15) ?
C11B C10B H10B . . 119.8 ?
C9B C10B H10B . . 119.8 ?
C10B C11B C12B . . 119.94(15) ?
C10B C11B H11B . . 120.0 ?
C12B C11B H11B . . 120.0 ?
C11B C12B C13B . . 120.24(14) ?
C11B C12B H12B . . 119.9 ?
C13B C12B H12B . . 119.9 ?
C12B C13B C8B . . 120.10(13) ?
C12B C13B H13B . . 120.0 ?
C8B C13B H13B . . 120.0 ?
N1B C14B C15B . . 111.15(11) ?
N1B C14B H14C . . 109.4 ?
C15B C14B H14C . . 109.4 ?
N1B C14B H14D . . 109.4 ?
C15B C14B H14D . . 109.4 ?
H14C C14B H14D . . 108.0 ?
O1B C15B C14B . . 112.51(11) ?
O1B C15B H15C . . 109.1 ?
C14B C15B H15C . . 109.1 ?
O1B C15B H15D . . 109.1 ?
C14B C15B H15D . . 109.1 ?
H15C C15B H15D . . 107.8 ?
O2B C16B O3B . . 123.64(14) ?
O2B C16B C4B . . 124.81(14) ?
O3B C16B C4B . . 111.55(12) ?
O3B C17B C18B . . 106.85(14) ?
O3B C17B H17C . . 110.4 ?
C18B C17B H17C . . 110.4 ?
O3B C17B H17D . . 110.4 ?
C18B C17B H17D . . 110.4 ?
H17C C17B H17D . . 108.6 ?
C17B C18B H18D . . 109.5 ?
C17B C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
C17B C18B H18F . . 109.5 ?
H18D C18B H18F . . 109.5 ?
H18E C18B H18F . . 109.5 ?
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
O1A C15A . 1.4186(18) ?
O1A H1OA . 0.81(2) ?
O2A C16A . 1.2085(19) ?
O3A C16A . 1.3427(18) ?
O3A C17A . 1.4564(18) ?
N1A C7A . 1.3772(18) ?
N1A C1A . 1.3801(17) ?
N1A C14A . 1.4647(18) ?
N2A C7A . 1.3328(18) ?
N2A C6A . 1.3879(18) ?
C1A C2A . 1.4007(19) ?
C1A C6A . 1.4048(19) ?
C2A C3A . 1.386(2) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.413(2) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.393(2) ?
C4A C16A . 1.484(2) ?
C5A C6A . 1.3889(19) ?
C5A H5AA . 0.9300 ?
C7A C8A . 1.471(2) ?
C8A C13A . 1.396(2) ?
C8A C9A . 1.4030(19) ?
C9A C10A . 1.384(2) ?
C9A H9AA . 0.9300 ?
C10A C11A . 1.387(2) ?
C10A H10A . 0.9300 ?
C11A C12A . 1.389(2) ?
C11A H11A . 0.9300 ?
C12A C13A . 1.386(2) ?
C12A H12A . 0.9300 ?
C13A H13A . 0.9300 ?
C14A C15A . 1.522(2) ?
C14A H14A . 0.9700 ?
C14A H14B . 0.9700 ?
C15A H15A . 0.9700 ?
C15A H15B . 0.9700 ?
C17A C18A . 1.505(2) ?
C17A H17A . 0.9700 ?
C17A H17B . 0.9700 ?
C18A H18A . 0.9600 ?
C18A H18B . 0.9600 ?
C18A H18C . 0.9600 ?
O1B C15B . 1.4109(18) ?
O1B H1OB . 0.98(3) ?
O2B C16B . 1.2069(18) ?
O3B C16B . 1.3484(18) ?
O3B C17B . 1.4463(19) ?
N1B C7B . 1.3779(17) ?
N1B C1B . 1.3815(18) ?
N1B C14B . 1.4563(17) ?
N2B C7B . 1.3306(18) ?
N2B C6B . 1.3900(18) ?
C1B C2B . 1.3953(19) ?
C1B C6B . 1.4037(18) ?
C2B C3B . 1.384(2) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.408(2) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.3892(19) ?
C4B C16B . 1.488(2) ?
C5B C6B . 1.3915(19) ?
C5B H5BA . 0.9300 ?
C7B C8B . 1.472(2) ?
C8B C9B . 1.398(2) ?
C8B C13B . 1.402(2) ?
C9B C10B . 1.390(2) ?
C9B H9BA . 0.9300 ?
C10B C11B . 1.386(2) ?
C10B H10B . 0.9300 ?
C11B C12B . 1.388(2) ?
C11B H11B . 0.9300 ?
C12B C13B . 1.390(2) ?
C12B H12B . 0.9300 ?
C13B H13B . 0.9300 ?
C14B C15B . 1.5221(19) ?
C14B H14C . 0.9700 ?
C14B H14D . 0.9700 ?
C15B H15C . 0.9700 ?
C15B H15D . 0.9700 ?
C17B C18B . 1.504(2) ?
C17B H17C . 0.9700 ?
C17B H17D . 0.9700 ?
C18B H18D . 0.9600 ?
C18B H18E . 0.9600 ?
C18B H18F . 0.9600 ?
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
O1A H1OA N2B . 0.81(3) 1.96(3) 2.7700(19) 177(3) yes
O1B H1OB N2A . 0.98(3) 1.89(3) 2.8680(18) 177(2) yes
C2B H2BA O1A 1_455 0.9300 2.4200 3.238(2) 146.00 yes
C12B H12B O1B 2_666 0.9300 2.5500 3.416(2) 155.00 yes
C13A H13A O1A . 0.9300 2.4000 3.273(2) 157.00 yes
C13B H13B O1B . 0.9300 2.4300 3.300(2) 155.00 yes
C15A H15B O2A 1_655 0.9700 2.5300 3.135(2) 120.00 yes
C17B H17D O2B 2_787 0.9700 2.5400 3.282(2) 133.00 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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7A N1A C1A C2A . . . . 176.50(14) ?
C14A N1A C1A C2A . . . . -4.2(2) ?
C7A N1A C1A C6A . . . . -1.25(14) ?
C14A N1A C1A C6A . . . . 178.06(12) ?
N1A C1A C2A C3A . . . . -178.13(13) ?
C6A C1A C2A C3A . . . . -0.7(2) ?
C1A C2A C3A C4A . . . . -0.4(2) ?
C2A C3A C4A C5A . . . . 1.0(2) ?
C2A C3A C4A C16A . . . . -178.65(13) ?
C3A C4A C5A C6A . . . . -0.5(2) ?
C16A C4A C5A C6A . . . . 179.14(12) ?
C7A N2A C6A C5A . . . . -178.09(14) ?
C7A N2A C6A C1A . . . . 0.21(15) ?
C4A C5A C6A N2A . . . . 177.63(13) ?
C4A C5A C6A C1A . . . . -0.5(2) ?
N1A C1A C6A N2A . . . . 0.67(15) ?
C2A C1A C6A N2A . . . . -177.34(12) ?
N1A C1A C6A C5A . . . . 179.17(12) ?
C2A C1A C6A C5A . . . . 1.2(2) ?
C6A N2A C7A N1A . . . . -1.05(15) ?
C6A N2A C7A C8A . . . . 173.07(12) ?
C1A N1A C7A N2A . . . . 1.49(15) ?
C14A N1A C7A N2A . . . . -177.76(12) ?
C1A N1A C7A C8A . . . . -172.31(12) ?
C14A N1A C7A C8A . . . . 8.4(2) ?
N2A C7A C8A C13A . . . . 145.39(14) ?
N1A C7A C8A C13A . . . . -41.3(2) ?
N2A C7A C8A C9A . . . . -33.94(19) ?
N1A C7A C8A C9A . . . . 139.34(14) ?
C13A C8A C9A C10A . . . . 2.0(2) ?
C7A C8A C9A C10A . . . . -178.61(13) ?
C8A C9A C10A C11A . . . . 0.1(2) ?
C9A C10A C11A C12A . . . . -1.8(2) ?
C10A C11A C12A C13A . . . . 1.3(2) ?
C11A C12A C13A C8A . . . . 0.9(2) ?
C9A C8A C13A C12A . . . . -2.5(2) ?
C7A C8A C13A C12A . . . . 178.16(14) ?
C7A N1A C14A C15A . . . . 102.15(16) ?
C1A N1A C14A C15A . . . . -76.99(16) ?
N1A C14A C15A O1A . . . . -69.79(15) ?
C17A O3A C16A O2A . . . . -0.9(2) ?
C17A O3A C16A C4A . . . . 178.92(12) ?
C5A C4A C16A O2A . . . . -6.3(2) ?
C3A C4A C16A O2A . . . . 173.36(14) ?
C5A C4A C16A O3A . . . . 173.93(12) ?
C3A C4A C16A O3A . . . . -6.43(19) ?
C16A O3A C17A C18A . . . . 73.83(18) ?
C7B N1B C1B C2B . . . . 177.03(14) ?
C14B N1B C1B C2B . . . . -5.3(2) ?
C7B N1B C1B C6B . . . . -1.51(14) ?
C14B N1B C1B C6B . . . . 176.20(11) ?
N1B C1B C2B C3B . . . . 179.89(13) ?
C6B C1B C2B C3B . . . . -1.8(2) ?
C1B C2B C3B C4B . . . . -1.0(2) ?
C2B C3B C4B C5B . . . . 1.9(2) ?
C2B C3B C4B C16B . . . . -176.95(13) ?
C3B C4B C5B C6B . . . . 0.0(2) ?
C16B C4B C5B C6B . . . . 178.85(12) ?
C7B N2B C6B C5B . . . . 178.20(14) ?
C7B N2B C6B C1B . . . . -0.70(15) ?
C4B C5B C6B N2B . . . . 178.57(13) ?
C4B C5B C6B C1B . . . . -2.63(19) ?
N1B C1B C6B N2B . . . . 1.40(14) ?
C2B C1B C6B N2B . . . . -177.30(12) ?
N1B C1B C6B C5B . . . . -177.64(12) ?
C2B C1B C6B C5B . . . . 3.7(2) ?
C6B N2B C7B N1B . . . . -0.29(15) ?
C6B N2B C7B C8B . . . . 175.92(12) ?
C1B N1B C7B N2B . . . . 1.17(15) ?
C14B N1B C7B N2B . . . . -176.30(12) ?
C1B N1B C7B C8B . . . . -174.89(12) ?
C14B N1B C7B C8B . . . . 7.6(2) ?
N2B C7B C8B C9B . . . . -37.4(2) ?
N1B C7B C8B C9B . . . . 138.34(15) ?
N2B C7B C8B C13B . . . . 141.16(14) ?
N1B C7B C8B C13B . . . . -43.1(2) ?
C13B C8B C9B C10B . . . . 0.0(2) ?
C7B C8B C9B C10B . . . . 178.61(15) ?
C8B C9B C10B C11B . . . . 1.1(3) ?
C9B C10B C11B C12B . . . . -1.4(3) ?
C10B C11B C12B C13B . . . . 0.6(3) ?
C11B C12B C13B C8B . . . . 0.5(2) ?
C9B C8B C13B C12B . . . . -0.8(2) ?
C7B C8B C13B C12B . . . . -179.33(13) ?
C7B N1B C14B C15B . . . . 104.85(16) ?
C1B N1B C14B C15B . . . . -72.28(16) ?
N1B C14B C15B O1B . . . . -64.92(15) ?
C17B O3B C16B O2B . . . . -1.5(2) ?
C17B O3B C16B C4B . . . . 178.76(12) ?
C5B C4B C16B O2B . . . . 3.6(2) ?
C3B C4B C16B O2B . . . . -177.50(14) ?
C5B C4B C16B O3B . . . . -176.65(12) ?
C3B C4B C16B O3B . . . . 2.24(19) ?
C16B O3B C17B C18B . . . . 167.61(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079152
