##############################################################################
#                                                                            #
# 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     2011-08-15
_journal_date_accepted     2011-09-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     10
_journal_page_first     o2704
_journal_page_last     o2704
_journal_paper_category     QO
_journal_coeditor_code     BH2376
_publ_contact_author_name     'Abd Hamid, Shafida'
_publ_contact_author_address
;
 Kulliiyah of Science, International Islamic University Malaysia
 Bandar Indera Mahkota, 25200 Kuantan Pahang
;
_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
;
Ethyl 1-(2-hydroxyethyl)-2-propyl-1H-benzimidazole-5-carboxylate
;
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
and
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
;
Ethyl 1-(2-hydroxyethyl)-2-propyl-1H-benzimidazole-5-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H20 N2 O3'
_chemical_formula_sum     'C15 H20 N2 O3'
_chemical_formula_iupac     'C15 H20 N2 O3'
_chemical_formula_weight     276.33
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.5081(3)
_cell_length_b     8.5573(3)
_cell_length_c     10.0117(4)
_cell_angle_alpha     94.671(3)
_cell_angle_beta     106.903(2)
_cell_angle_gamma     98.334(3)
_cell_volume     684.16(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5332
_cell_measurement_theta_min     2.1
_cell_measurement_theta_max     25.0
_cell_measurement_temperature     100(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.341
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     296
_exptl_absorpt_coefficient_mu     0.094
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9461
_exptl_absorpt_correction_T_max     0.9935
_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
;
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     83.66
_diffrn_reflns_number     10526
_diffrn_reflns_av_R_equivalents     0.0259
_diffrn_reflns_av_sigmaI/netI     0.0240
_diffrn_reflns_theta_min     2.1
_diffrn_reflns_theta_max     25.0
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     1.0
_diffrn_measured_fraction_theta_full     1.0
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     2401
_reflns_number_gt     2075
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0433
_refine_ls_R_factor_gt     0.0358
_refine_ls_wR_factor_gt     0.0827
_refine_ls_wR_factor_ref     0.0865
_refine_ls_goodness_of_fit_ref     1.082
_refine_ls_restrained_S_all     1.082
_refine_ls_number_reflns     2401
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0378P)²+0.2619P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.20
_refine_diff_density_min     -0.25
_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 0.27470(12) 0.59246(12) 0.65294(11) 0.0183(3) Uani d . 1 1 . .
    O O2 0.45117(13) 0.43517(13) 0.75699(12) 0.0241(3) Uani d . 1 1 . .
    O O3 -0.40580(13) -0.06135(12) 0.88681(11) 0.0184(3) Uani d . 1 1 . .
    H H3A -0.315(3) -0.088(2) 0.879(2) 0.045(6) Uiso d . 1 1 . .
    N N1 -0.14250(14) 0.23821(13) 0.99931(12) 0.0132(3) Uani d . 1 1 . .
    N N2 0.12077(14) 0.19893(14) 1.09005(12) 0.0138(3) Uani d . 1 1 . .
    C C1 0.11012(17) 0.28238(16) 0.97476(15) 0.0134(3) Uani d . 1 1 . .
    C C2 0.23274(18) 0.33848(16) 0.91519(15) 0.0145(3) Uani d . 1 1 . .
    H H2A 0.3441 0.3213 0.9524 0.017 Uiso calc R 1 1 . .
    C C3 0.18718(18) 0.42060(16) 0.79936(15) 0.0146(3) Uani d . 1 1 . .
    C C4 0.02190(18) 0.44787(17) 0.74524(15) 0.0152(3) Uani d . 1 1 . .
    H H4A -0.0053 0.5061 0.6673 0.018 Uiso calc R 1 1 . .
    C C5 -0.10116(18) 0.39202(16) 0.80289(15) 0.0149(3) Uani d . 1 1 . .
    H H5A -0.2123 0.4100 0.7663 0.018 Uiso calc R 1 1 . .
    C C6 -0.05419(17) 0.30799(16) 0.91746(14) 0.0130(3) Uani d . 1 1 . .
    C C7 -0.03154(17) 0.17548(16) 1.10106(15) 0.0134(3) Uani d . 1 1 . .
    C C8 0.31874(18) 0.48006(17) 0.73628(15) 0.0160(3) Uani d . 1 1 . .
    C C9 0.39782(19) 0.65961(18) 0.58856(17) 0.0207(4) Uani d . 1 1 . .
    H H9A 0.3987 0.5840 0.5086 0.025 Uiso calc R 1 1 . .
    H H9B 0.5106 0.6813 0.6582 0.025 Uiso calc R 1 1 . .
    C C10 0.3502(2) 0.81088(19) 0.53830(17) 0.0239(4) Uani d . 1 1 . .
    H H10A 0.4265 0.8557 0.4888 0.036 Uiso calc R 1 1 . .
    H H10B 0.3571 0.8873 0.6191 0.036 Uiso calc R 1 1 . .
    H H10C 0.2357 0.7889 0.4741 0.036 Uiso calc R 1 1 . .
    C C11 -0.32301(17) 0.22441(17) 0.97243(15) 0.0147(3) Uani d . 1 1 . .
    H H11A -0.3564 0.3274 0.9492 0.018 Uiso calc R 1 1 . .
    H H11B -0.3508 0.2007 1.0589 0.018 Uiso calc R 1 1 . .
    C C12 -0.42069(18) 0.09446(17) 0.85251(15) 0.0162(3) Uani d . 1 1 . .
    H H12A -0.5400 0.1044 0.8252 0.019 Uiso calc R 1 1 . .
    H H12B -0.3809 0.1103 0.7701 0.019 Uiso calc R 1 1 . .
    C C13 -0.08488(18) 0.09237(17) 1.21037(15) 0.0158(3) Uani d . 1 1 . .
    H H13A -0.1637 -0.0071 1.1638 0.019 Uiso calc R 1 1 . .
    H H13B -0.1456 0.1610 1.2540 0.019 Uiso calc R 1 1 . .
    C C14 0.05897(19) 0.05117(18) 1.32650(16) 0.0184(3) Uani d . 1 1 . .
    H H14A 0.0130 -0.0277 1.3786 0.022 Uiso calc R 1 1 . .
    H H14B 0.1328 0.0009 1.2827 0.022 Uiso calc R 1 1 . .
    C C15 0.1621(2) 0.19530(19) 1.43011(16) 0.0238(4) Uani d . 1 1 . .
    H H15A 0.2517 0.1615 1.5019 0.036 Uiso calc R 1 1 . .
    H H15B 0.0904 0.2445 1.4754 0.036 Uiso calc R 1 1 . .
    H H15C 0.2107 0.2727 1.3797 0.036 Uiso calc R 1 1 . .
_geom_special_details     ?
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 . 1.3471(17) ?
    O1 C9 . 1.4565(18) ?
    O2 C8 . 1.2094(18) ?
    O3 C12 . 1.4177(17) ?
    O3 H3A . 0.86(2) ?
    N1 C7 . 1.3762(18) ?
    N1 C6 . 1.3785(19) ?
    N1 C11 . 1.4653(18) ?
    N2 C7 . 1.3202(18) ?
    N2 C1 . 1.3937(18) ?
    C1 C2 . 1.392(2) ?
    C1 C6 . 1.405(2) ?
    C2 C3 . 1.393(2) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.414(2) ?
    C3 C8 . 1.486(2) ?
    C4 C5 . 1.382(2) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.394(2) ?
    C5 H5A . 0.9500 ?
    C7 C13 . 1.494(2) ?
    C9 C10 . 1.494(2) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 C12 . 1.518(2) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.529(2) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C15 . 1.522(2) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 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 O1 C9 . . 115.89(11) ?
    C12 O3 H3A . . 111.6(14) ?
    C7 N1 C6 . . 106.93(11) ?
    C7 N1 C11 . . 127.84(12) ?
    C6 N1 C11 . . 125.05(12) ?
    C7 N2 C1 . . 105.09(11) ?
    C2 C1 N2 . . 130.08(13) ?
    C2 C1 C6 . . 120.14(13) ?
    N2 C1 C6 . . 109.77(12) ?
    C1 C2 C3 . . 117.98(13) ?
    C1 C2 H2A . . 121.0 ?
    C3 C2 H2A . . 121.0 ?
    C2 C3 C4 . . 120.92(13) ?
    C2 C3 C8 . . 117.67(13) ?
    C4 C3 C8 . . 121.40(13) ?
    C5 C4 C3 . . 121.66(13) ?
    C5 C4 H4A . . 119.2 ?
    C3 C4 H4A . . 119.2 ?
    C4 C5 C6 . . 116.73(13) ?
    C4 C5 H5A . . 121.6 ?
    C6 C5 H5A . . 121.6 ?
    N1 C6 C5 . . 131.94(13) ?
    N1 C6 C1 . . 105.49(12) ?
    C5 C6 C1 . . 122.55(13) ?
    N2 C7 N1 . . 112.72(12) ?
    N2 C7 C13 . . 125.88(13) ?
    N1 C7 C13 . . 121.40(12) ?
    O2 C8 O1 . . 123.07(13) ?
    O2 C8 C3 . . 124.77(13) ?
    O1 C8 C3 . . 112.16(12) ?
    O1 C9 C10 . . 107.38(12) ?
    O1 C9 H9A . . 110.2 ?
    C10 C9 H9A . . 110.2 ?
    O1 C9 H9B . . 110.2 ?
    C10 C9 H9B . . 110.2 ?
    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 ?
    N1 C11 C12 . . 111.97(11) ?
    N1 C11 H11A . . 109.2 ?
    C12 C11 H11A . . 109.2 ?
    N1 C11 H11B . . 109.2 ?
    C12 C11 H11B . . 109.2 ?
    H11A C11 H11B . . 107.9 ?
    O3 C12 C11 . . 113.35(12) ?
    O3 C12 H12A . . 108.9 ?
    C11 C12 H12A . . 108.9 ?
    O3 C12 H12B . . 108.9 ?
    C11 C12 H12B . . 108.9 ?
    H12A C12 H12B . . 107.7 ?
    C7 C13 C14 . . 114.12(12) ?
    C7 C13 H13A . . 108.7 ?
    C14 C13 H13A . . 108.7 ?
    C7 C13 H13B . . 108.7 ?
    C14 C13 H13B . . 108.7 ?
    H13A C13 H13B . . 107.6 ?
    C15 C14 C13 . . 113.25(12) ?
    C15 C14 H14A . . 108.9 ?
    C13 C14 H14A . . 108.9 ?
    C15 C14 H14B . . 108.9 ?
    C13 C14 H14B . . 108.9 ?
    H14A C14 H14B . . 107.7 ?
    C14 C15 H15A . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C14 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 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 N2 C1 C2 . . . . 179.98(14) ?
    C7 N2 C1 C6 . . . . 0.06(15) ?
    N2 C1 C2 C3 . . . . -179.43(14) ?
    C6 C1 C2 C3 . . . . 0.5(2) ?
    C1 C2 C3 C4 . . . . 0.8(2) ?
    C1 C2 C3 C8 . . . . -179.97(12) ?
    C2 C3 C4 C5 . . . . -1.2(2) ?
    C8 C3 C4 C5 . . . . 179.59(13) ?
    C3 C4 C5 C6 . . . . 0.3(2) ?
    C7 N1 C6 C5 . . . . -178.15(14) ?
    C11 N1 C6 C5 . . . . 6.4(2) ?
    C7 N1 C6 C1 . . . . 0.39(14) ?
    C11 N1 C6 C1 . . . . -175.07(12) ?
    C4 C5 C6 N1 . . . . 179.43(13) ?
    C4 C5 C6 C1 . . . . 1.1(2) ?
    C2 C1 C6 N1 . . . . 179.78(12) ?
    N2 C1 C6 N1 . . . . -0.28(15) ?
    C2 C1 C6 C5 . . . . -1.5(2) ?
    N2 C1 C6 C5 . . . . 178.43(12) ?
    C1 N2 C7 N1 . . . . 0.20(15) ?
    C1 N2 C7 C13 . . . . -179.22(13) ?
    C6 N1 C7 N2 . . . . -0.39(15) ?
    C11 N1 C7 N2 . . . . 174.91(12) ?
    C6 N1 C7 C13 . . . . 179.07(12) ?
    C11 N1 C7 C13 . . . . -5.6(2) ?
    C9 O1 C8 O2 . . . . -0.5(2) ?
    C9 O1 C8 C3 . . . . 178.95(12) ?
    C2 C3 C8 O2 . . . . 16.6(2) ?
    C4 C3 C8 O2 . . . . -164.22(14) ?
    C2 C3 C8 O1 . . . . -162.86(12) ?
    C4 C3 C8 O1 . . . . 16.34(19) ?
    C8 O1 C9 C10 . . . . -163.28(12) ?
    C7 N1 C11 C12 . . . . -98.59(16) ?
    C6 N1 C11 C12 . . . . 75.92(16) ?
    N1 C11 C12 O3 . . . . 70.35(16) ?
    N2 C7 C13 C14 . . . . 7.5(2) ?
    N1 C7 C13 C14 . . . . -171.87(12) ?
    C7 C13 C14 C15 . . . . 73.93(16) ?
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
    O3 H3A N2 . . 2_557 0.86(3) 1.98(2) 2.8047(17) 159.6(17) yes
    C11 H11A O2 . . 1_455 0.99 2.48 3.2901(19) 139 yes
    C11 H11B O3 . . 2_457 0.99 2.46 3.2457(19) 136 no
