#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/31/2233125.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_2233125
loop_
_publ_author_name
'Hamzah, Nurasyikin'
'Ngah, Nurziana'
'Abd Hamid, Shafida'
'Abdul Rahim, Aisyah Saad'
_publ_section_title
;
 Ethyl
 1-(2-hydroxyethyl)-2-[2-(methylsulfanyl)ethyl]-1H-benzimidazole-5-carboxylate
;
_journal_coeditor_code           CV5217
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o197
_journal_page_last               o198
_journal_paper_doi               10.1107/S160053681105389X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H20 N2 O3 S'
_chemical_formula_moiety         'C15 H20 N2 O3 S'
_chemical_formula_sum            'C15 H20 N2 O3 S'
_chemical_formula_weight         308.39
_chemical_name_systematic
;
Ethyl 1-(2-hydroxyethyl)-2-[2-(methylsulfanyl)ethyl]-
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                110.2180(10)
_cell_angle_beta                 102.5290(10)
_cell_angle_gamma                99.1010(10)
_cell_formula_units_Z            2
_cell_length_a                   8.39090(10)
_cell_length_b                   8.8277(2)
_cell_length_c                   11.5025(2)
_cell_measurement_reflns_used    2401
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.9
_cell_volume                     754.78(2)
_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(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω scan'
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6027
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.9
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_correction_T_min  0.9408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2627
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0307P)²+0.5234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                2243
_reflns_number_total             2627
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv5217.cif
_cod_data_source_block           I
_cod_database_code               2233125
_cod_database_fobs_code          2233125
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_symmetry_multiplicity
S S1 1.33465(6) 0.81922(6) 0.91756(5) 0.02048(15) Uani d . 1 1
O O1 0.36330(17) -0.07772(17) 0.28863(14) 0.0244(3) Uani d . 1 1
O O2 0.46252(16) -0.29862(16) 0.19992(13) 0.0195(3) Uani d . 1 1
O O3 1.32576(17) 0.48466(17) 0.39325(14) 0.0213(3) Uani d D 1 1
H H3 1.2305(18) 0.505(3) 0.391(2) 0.035(7) Uiso d D 1 1
N N1 0.94054(19) 0.36073(19) 0.58614(15) 0.0151(3) Uani d . 1 1
N N2 1.14023(19) 0.26662(19) 0.50164(15) 0.0140(3) Uani d . 1 1
C C1 0.8668(2) 0.2070(2) 0.48209(18) 0.0140(4) Uani d . 1 1
C C2 0.6994(2) 0.1144(2) 0.43009(18) 0.0158(4) Uani d . 1 1
H H2 0.6138 0.1549 0.4640 0.019 Uiso calc R 1 1
C C3 0.6610(2) -0.0396(2) 0.32689(18) 0.0153(4) Uani d . 1 1
C C4 0.7890(2) -0.0998(2) 0.27731(18) 0.0166(4) Uani d . 1 1
H H4 0.7597 -0.2063 0.2081 0.020 Uiso calc R 1 1
C C5 0.9553(2) -0.0084(2) 0.32637(18) 0.0164(4) Uani d . 1 1
H H5 1.0408 -0.0485 0.2921 0.020 Uiso calc R 1 1
C C6 0.9912(2) 0.1465(2) 0.42935(18) 0.0141(4) Uani d . 1 1
C C7 1.1022(2) 0.3904(2) 0.59415(18) 0.0145(4) Uani d . 1 1
C C8 0.4814(2) -0.1364(2) 0.27111(18) 0.0169(4) Uani d . 1 1
C C9 0.2882(3) -0.3974(2) 0.1397(2) 0.0231(5) Uani d . 1 1
H H9A 0.2271 -0.3537 0.0798 0.028 Uiso calc R 1 1
H H9B 0.2301 -0.3927 0.2067 0.028 Uiso calc R 1 1
C C10 0.2919(3) -0.5719(3) 0.0675(2) 0.0391(6) Uani d . 1 1
H H10A 0.3534 -0.5743 0.0038 0.059 Uiso calc R 1 1
H H10B 0.1762 -0.6412 0.0227 0.059 Uiso calc R 1 1
H H10C 0.3486 -0.6153 0.1282 0.059 Uiso calc R 1 1
C C11 1.3032(2) 0.2629(2) 0.47536(19) 0.0165(4) Uani d . 1 1
H H11A 1.3195 0.1490 0.4552 0.020 Uiso calc R 1 1
H H11B 1.3949 0.3403 0.5538 0.020 Uiso calc R 1 1
C C12 1.3139(2) 0.3126(2) 0.36286(19) 0.0181(4) Uani d . 1 1
H H12A 1.4139 0.2852 0.3363 0.022 Uiso calc R 1 1
H H12B 1.2125 0.2463 0.2884 0.022 Uiso calc R 1 1
C C13 1.2355(2) 0.5380(2) 0.69567(18) 0.0171(4) Uani d . 1 1
H H13A 1.2923 0.6013 0.6533 0.021 Uiso calc R 1 1
H H13B 1.3214 0.4989 0.7436 0.021 Uiso calc R 1 1
C C14 1.1634(2) 0.6532(2) 0.79092(18) 0.0179(4) Uani d . 1 1
H H14A 1.0995 0.5893 0.8293 0.022 Uiso calc R 1 1
H H14B 1.0850 0.7012 0.7452 0.022 Uiso calc R 1 1
C C15 1.2132(3) 0.9482(3) 0.9979(2) 0.0253(5) Uani d . 1 1
H H15A 1.1466 0.9862 0.9373 0.038 Uiso calc R 1 1
H H15B 1.2896 1.0452 1.0725 0.038 Uiso calc R 1 1
H H15C 1.1373 0.8836 1.0275 0.038 Uiso calc R 1 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'
S S 0.1246 0.1234 '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
C15 S1 C14 99.19(10)
C8 O2 C9 114.83(15)
C12 O3 H3 110.8(17)
C7 N1 C1 104.86(15)
C7 N2 C6 106.81(14)
C7 N2 C11 128.13(16)
C6 N2 C11 124.94(15)
C2 C1 N1 130.07(17)
C2 C1 C6 120.17(17)
N1 C1 C6 109.76(16)
C1 C2 C3 118.05(17)
C1 C2 H2 121.0
C3 C2 H2 121.0
C2 C3 C4 120.76(17)
C2 C3 C8 117.54(17)
C4 C3 C8 121.69(17)
C5 C4 C3 121.96(18)
C5 C4 H4 119.0
C3 C4 H4 119.0
C4 C5 C6 116.42(17)
C4 C5 H5 121.8
C6 C5 H5 121.8
N2 C6 C5 131.88(17)
N2 C6 C1 105.50(16)
C5 C6 C1 122.61(17)
N1 C7 N2 113.06(17)
N1 C7 C13 124.93(16)
N2 C7 C13 121.95(16)
O1 C8 O2 122.83(18)
O1 C8 C3 124.28(18)
O2 C8 C3 112.88(16)
O2 C9 C10 107.31(17)
O2 C9 H9A 110.3
C10 C9 H9A 110.3
O2 C9 H9B 110.3
C10 C9 H9B 110.3
H9A C9 H9B 108.5
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N2 C11 C12 111.81(15)
N2 C11 H11A 109.3
C12 C11 H11A 109.3
N2 C11 H11B 109.3
C12 C11 H11B 109.3
H11A C11 H11B 107.9
O3 C12 C11 113.02(16)
O3 C12 H12A 109.0
C11 C12 H12A 109.0
O3 C12 H12B 109.0
C11 C12 H12B 109.0
H12A C12 H12B 107.8
C7 C13 C14 112.12(15)
C7 C13 H13A 109.2
C14 C13 H13A 109.2
C7 C13 H13B 109.2
C14 C13 H13B 109.2
H13A C13 H13B 107.9
C13 C14 S1 109.23(13)
C13 C14 H14A 109.8
S1 C14 H14A 109.8
C13 C14 H14B 109.8
S1 C14 H14B 109.8
H14A C14 H14B 108.3
S1 C15 H15A 109.5
S1 C15 H15B 109.5
H15A C15 H15B 109.5
S1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C15 1.799(2)
S1 C14 1.812(2)
O1 C8 1.212(2)
O2 C8 1.345(2)
O2 C9 1.456(2)
O3 C12 1.417(2)
O3 H3 0.843(10)
N1 C7 1.317(2)
N1 C1 1.395(2)
N2 C7 1.372(2)
N2 C6 1.379(2)
N2 C11 1.466(2)
C1 C2 1.391(3)
C1 C6 1.403(2)
C2 C3 1.393(3)
C2 H2 0.9500
C3 C4 1.414(3)
C3 C8 1.485(3)
C4 C5 1.379(3)
C4 H4 0.9500
C5 C6 1.400(3)
C5 H5 0.9500
C7 C13 1.495(3)
C9 C10 1.485(3)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.518(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.521(3)
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
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
O3 H3 N1 2_766 0.844(17) 2.01(2) 2.808(2) 159(2) yes
C11 H11A O1 1_655 0.99 2.39 3.224(2) 142 yes
C11 H11B O3 2_866 0.99 2.42 3.222(2) 138 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
C7 N1 C1 C2 179.65(19)
C7 N1 C1 C6 0.33(19)
N1 C1 C2 C3 -178.17(17)
C6 C1 C2 C3 1.1(3)
C1 C2 C3 C4 0.4(3)
C1 C2 C3 C8 -179.23(16)
C2 C3 C4 C5 -1.4(3)
C8 C3 C4 C5 178.19(17)
C3 C4 C5 C6 0.8(3)
C7 N2 C6 C5 -177.37(19)
C11 N2 C6 C5 6.4(3)
C7 N2 C6 C1 1.00(19)
C11 N2 C6 C1 -175.20(16)
C4 C5 C6 N2 178.81(18)
C4 C5 C6 C1 0.7(3)
C2 C1 C6 N2 179.76(16)
N1 C1 C6 N2 -0.84(19)
C2 C1 C6 C5 -1.7(3)
N1 C1 C6 C5 177.72(16)
C1 N1 C7 N2 0.3(2)
C1 N1 C7 C13 -177.00(17)
C6 N2 C7 N1 -0.9(2)
C11 N2 C7 N1 175.16(16)
C6 N2 C7 C13 176.55(16)
C11 N2 C7 C13 -7.4(3)
C9 O2 C8 O1 3.0(3)
C9 O2 C8 C3 -178.05(15)
C2 C3 C8 O1 16.9(3)
C4 C3 C8 O1 -162.71(18)
C2 C3 C8 O2 -162.02(16)
C4 C3 C8 O2 18.4(2)
C8 O2 C9 C10 -179.17(17)
C7 N2 C11 C12 -98.5(2)
C6 N2 C11 C12 76.8(2)
N2 C11 C12 O3 70.8(2)
N1 C7 C13 C14 0.0(3)
N2 C7 C13 C14 -177.14(16)
C7 C13 C14 S1 175.48(13)
C15 S1 C14 C13 171.67(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657312
