#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220774.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_2220774
loop_
_publ_author_name
'Rominger, Frank'
'Malathi, Mahalingam'
'Mohan, Palathurai Subramaniam'
'Ramamurthi Dondeti, Tanuja'
'Hashmi, A. Stephen K.'
_publ_section_title
;
 2-{2-[3-(1H-Benzimidazol-2-yl)quinolin-2-yloxy]ethoxy}ethanol
;
_journal_coeditor_code           FJ2184
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o401
_journal_paper_doi               10.1107/S1600536809002797
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H19 N3 O3'
_chemical_formula_moiety         'C20 H19 N3 O3'
_chemical_formula_sum            'C20 H19 N3 O3'
_chemical_formula_weight         349.38
_chemical_name_systematic
;
2-{2-[3-(1H-Benzimidazol-2-yl)quinolin-2-yloxy]ethoxy}ethanol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 118.7440(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9478(2)
_cell_length_b                   13.13380(10)
_cell_length_c                   12.4031(2)
_cell_measurement_reflns_used    7839
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.94
_cell_volume                     1706.47(4)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008a)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008a)'
_computing_structure_refinement  'SHELXTL ( Sheldrick, 2008a)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008a)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 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  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16400
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008b)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0440
_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)+(0.0424P)²+0.5312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                2890
_reflns_number_total             3920
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2184.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220774
_cod_database_fobs_code          2220774
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N N1 0.88443(12) 0.06208(10) 0.82383(11) 0.0329(3) Uani d . 1 . .
C C2 0.76960(14) 0.02903(11) 0.79014(13) 0.0292(3) Uani d . 1 . .
C C3 0.70017(13) 0.04708(11) 0.85560(13) 0.0280(3) Uani d . 1 . .
C C4 0.76217(14) 0.10173(11) 0.96231(13) 0.0296(3) Uani d . 1 . .
H H4 0.7203 0.1149 1.0094 0.036 Uiso calc R 1 . .
C C5 0.88674(14) 0.13885(11) 1.00364(13) 0.0313(3) Uani d . 1 . .
C C6 0.95367(16) 0.19686(13) 1.11232(15) 0.0390(4) Uani d . 1 . .
H H6 0.9141 0.2129 1.1608 0.047 Uiso calc R 1 . .
C C7 1.07435(17) 0.22987(14) 1.14778(16) 0.0453(4) Uani d . 1 . .
H H7 1.1192 0.2679 1.2216 0.054 Uiso calc R 1 . .
C C8 1.13282(17) 0.20803(14) 1.07591(17) 0.0452(4) Uani d . 1 . .
H H8 1.2171 0.2315 1.1015 0.054 Uiso calc R 1 . .
C C9 1.06998(16) 0.15334(13) 0.96934(16) 0.0401(4) Uani d . 1 . .
H H9 1.1105 0.1396 0.9212 0.048 Uiso calc R 1 . .
C C10 0.94551(14) 0.11733(11) 0.93079(14) 0.0315(3) Uani d . 1 . .
C C12 0.56784(13) 0.01642(11) 0.81376(13) 0.0276(3) Uani d . 1 . .
N N13 0.49537(12) 0.06596(9) 0.85027(11) 0.0306(3) Uani d . 1 . .
N N14 0.50501(12) -0.06326(9) 0.73809(11) 0.0296(3) Uani d . 1 . .
H H14 0.5367(18) -0.1089(15) 0.7031(17) 0.053(5) Uiso d . 1 . .
C C21 0.37911(14) 0.01587(11) 0.79551(13) 0.0300(3) Uani d . 1 . .
C C22 0.26652(15) 0.03860(13) 0.79847(15) 0.0376(4) Uani d . 1 . .
H H22 0.2627 0.0936 0.8463 0.045 Uiso calc R 1 . .
C C23 0.16163(16) -0.02100(14) 0.73012(16) 0.0427(4) Uani d . 1 . .
H H23 0.0837 -0.0065 0.7302 0.051 Uiso calc R 1 . .
C C24 0.16696(16) -0.10276(14) 0.66025(17) 0.0442(4) Uani d . 1 . .
H H24 0.0926 -0.1427 0.6143 0.053 Uiso calc R 1 . .
C C25 0.27764(16) -0.12678(13) 0.65644(15) 0.0395(4) Uani d . 1 . .
H H25 0.2813 -0.1825 0.6093 0.047 Uiso calc R 1 . .
C C26 0.38342(14) -0.06551(11) 0.72491(13) 0.0296(3) Uani d . 1 . .
O O31 0.70752(10) -0.02559(8) 0.68516(9) 0.0339(3) Uani d . 1 . .
C C32 0.77582(16) -0.04159(13) 0.61680(14) 0.0381(4) Uani d . 1 . .
H H32A 0.8550 -0.0808 0.6669 0.046 Uiso calc R 1 . .
H H32B 0.7993 0.0246 0.5951 0.046 Uiso calc R 1 . .
C C33 0.68995(17) -0.09925(12) 0.50313(14) 0.0396(4) Uani d . 1 . .
H H33A 0.6050 -0.0662 0.4615 0.048 Uiso calc R 1 . .
H H33B 0.7258 -0.0988 0.4459 0.048 Uiso calc R 1 . .
O O34 0.67706(11) -0.20130(8) 0.53374(10) 0.0383(3) Uani d . 1 . .
C C35 0.56108(17) -0.24765(13) 0.44759(15) 0.0427(4) Uani d . 1 . .
H H35A 0.5703 -0.3225 0.4563 0.051 Uiso calc R 1 . .
H H35B 0.5436 -0.2298 0.3634 0.051 Uiso calc R 1 . .
C C36 0.44979(17) -0.21515(14) 0.46430(17) 0.0470(4) Uani d . 1 . .
H H36A 0.4319 -0.1422 0.4429 0.056 Uiso calc R 1 . .
H H36B 0.3732 -0.2544 0.4074 0.056 Uiso calc R 1 . .
O O37 0.47303(13) -0.23023(9) 0.58596(12) 0.0464(3) Uani d . 1 . .
H H37 0.486(2) -0.300(2) 0.604(2) 0.077(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
C2 N1 C10 . . 118.33(13) ?
N1 C2 O31 . . 119.41(13) ?
N1 C2 C3 . . 124.84(14) ?
O31 C2 C3 . . 115.75(13) ?
C4 C3 C2 . . 116.32(13) ?
C4 C3 C12 . . 118.51(13) ?
C2 C3 C12 . . 125.09(13) ?
C3 C4 C5 . . 121.31(14) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C4 C5 C10 . . 117.46(14) ?
C4 C5 C6 . . 123.21(14) ?
C10 C5 C6 . . 119.33(14) ?
C7 C6 C5 . . 120.36(16) ?
C7 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C6 C7 C8 . . 120.28(16) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C9 C8 C7 . . 120.81(16) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C10 . . 120.26(16) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
N1 C10 C9 . . 119.30(14) ?
N1 C10 C5 . . 121.74(13) ?
C9 C10 C5 . . 118.95(15) ?
N13 C12 N14 . . 112.21(13) ?
N13 C12 C3 . . 121.05(13) ?
N14 C12 C3 . . 126.73(13) ?
C12 N13 C21 . . 105.40(12) ?
C12 N14 C26 . . 107.28(12) ?
C12 N14 H14 . . 127.4(12) ?
C26 N14 H14 . . 125.3(12) ?
N13 C21 C22 . . 129.64(14) ?
N13 C21 C26 . . 109.88(13) ?
C22 C21 C26 . . 120.41(14) ?
C23 C22 C21 . . 117.88(15) ?
C23 C22 H22 . . 121.1 ?
C21 C22 H22 . . 121.1 ?
C22 C23 C24 . . 121.35(16) ?
C22 C23 H23 . . 119.3 ?
C24 C23 H23 . . 119.3 ?
C25 C24 C23 . . 121.67(16) ?
C25 C24 H24 . . 119.2 ?
C23 C24 H24 . . 119.2 ?
C24 C25 C26 . . 116.78(15) ?
C24 C25 H25 . . 121.6 ?
C26 C25 H25 . . 121.6 ?
N14 C26 C25 . . 132.82(14) ?
N14 C26 C21 . . 105.24(13) ?
C25 C26 C21 . . 121.90(14) ?
C2 O31 C32 . . 115.99(12) ?
O31 C32 C33 . . 107.60(13) ?
O31 C32 H32A . . 110.2 ?
C33 C32 H32A . . 110.2 ?
O31 C32 H32B . . 110.2 ?
C33 C32 H32B . . 110.2 ?
H32A C32 H32B . . 108.5 ?
O34 C33 C32 . . 109.88(13) ?
O34 C33 H33A . . 109.7 ?
C32 C33 H33A . . 109.7 ?
O34 C33 H33B . . 109.7 ?
C32 C33 H33B . . 109.7 ?
H33A C33 H33B . . 108.2 ?
C35 O34 C33 . . 113.32(12) ?
O34 C35 C36 . . 112.53(14) ?
O34 C35 H35A . . 109.1 ?
C36 C35 H35A . . 109.1 ?
O34 C35 H35B . . 109.1 ?
C36 C35 H35B . . 109.1 ?
H35A C35 H35B . . 107.8 ?
O37 C36 C35 . . 112.06(15) ?
O37 C36 H36A . . 109.2 ?
C35 C36 H36A . . 109.2 ?
O37 C36 H36B . . 109.2 ?
C35 C36 H36B . . 109.2 ?
H36A C36 H36B . . 107.9 ?
C36 O37 H37 . . 108.8(14) ?
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
N1 C2 . 1.3015(19) ?
N1 C10 . 1.374(2) ?
C2 O31 . 1.3532(17) ?
C2 C3 . 1.432(2) ?
C3 C4 . 1.368(2) ?
C3 C12 . 1.464(2) ?
C4 C5 . 1.408(2) ?
C4 H4 . 0.9500 ?
C5 C10 . 1.414(2) ?
C5 C6 . 1.414(2) ?
C6 C7 . 1.360(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.401(3) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.368(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.407(2) ?
C9 H9 . 0.9500 ?
C12 N13 . 1.3248(18) ?
C12 N14 . 1.3646(19) ?
N13 C21 . 1.3843(19) ?
N14 C26 . 1.3818(19) ?
N14 H14 . 0.92(2) ?
C21 C22 . 1.396(2) ?
C21 C26 . 1.398(2) ?
C22 C23 . 1.371(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.400(3) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.382(2) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.391(2) ?
C25 H25 . 0.9500 ?
O31 C32 . 1.4472(18) ?
C32 C33 . 1.491(2) ?
C32 H32A . 0.9900 ?
C32 H32B . 0.9900 ?
C33 O34 . 1.4215(19) ?
C33 H33A . 0.9900 ?
C33 H33B . 0.9900 ?
O34 C35 . 1.417(2) ?
C35 C36 . 1.503(3) ?
C35 H35A . 0.9900 ?
C35 H35B . 0.9900 ?
C36 O37 . 1.411(2) ?
C36 H36A . 0.9900 ?
C36 H36B . 0.9900 ?
O37 H37 . 0.94(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
N14 H14 O37 1_555 0.92(2) 2.04(2) 2.797(2) 138.3(19)
O37 H37 N13 2_646 0.94(3) 1.83(3) 2.765(2) 175(2)
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
C10 N1 C2 O31 . . . . -179.98(13) ?
C10 N1 C2 C3 . . . . 0.9(2) ?
N1 C2 C3 C4 . . . . -1.2(2) ?
O31 C2 C3 C4 . . . . 179.63(13) ?
N1 C2 C3 C12 . . . . 175.39(14) ?
O31 C2 C3 C12 . . . . -3.7(2) ?
C2 C3 C4 C5 . . . . 0.8(2) ?
C12 C3 C4 C5 . . . . -176.08(13) ?
C3 C4 C5 C10 . . . . -0.1(2) ?
C3 C4 C5 C6 . . . . 179.06(14) ?
C4 C5 C6 C7 . . . . 179.50(15) ?
C10 C5 C6 C7 . . . . -1.3(2) ?
C5 C6 C7 C8 . . . . 1.0(3) ?
C6 C7 C8 C9 . . . . 0.0(3) ?
C7 C8 C9 C10 . . . . -0.6(3) ?
C2 N1 C10 C9 . . . . 179.66(14) ?
C2 N1 C10 C5 . . . . -0.2(2) ?
C8 C9 C10 N1 . . . . -179.64(15) ?
C8 C9 C10 C5 . . . . 0.2(2) ?
C4 C5 C10 N1 . . . . -0.2(2) ?
C6 C5 C10 N1 . . . . -179.44(14) ?
C4 C5 C10 C9 . . . . 179.96(14) ?
C6 C5 C10 C9 . . . . 0.7(2) ?
C4 C3 C12 N13 . . . . 22.5(2) ?
C2 C3 C12 N13 . . . . -154.07(14) ?
C4 C3 C12 N14 . . . . -156.31(14) ?
C2 C3 C12 N14 . . . . 27.1(2) ?
N14 C12 N13 C21 . . . . 0.02(16) ?
C3 C12 N13 C21 . . . . -178.94(12) ?
N13 C12 N14 C26 . . . . -0.11(16) ?
C3 C12 N14 C26 . . . . 178.78(13) ?
C12 N13 C21 C22 . . . . -176.95(16) ?
C12 N13 C21 C26 . . . . 0.07(16) ?
N13 C21 C22 C23 . . . . 176.58(15) ?
C26 C21 C22 C23 . . . . -0.2(2) ?
C21 C22 C23 C24 . . . . 0.6(3) ?
C22 C23 C24 C25 . . . . -0.3(3) ?
C23 C24 C25 C26 . . . . -0.3(3) ?
C12 N14 C26 C25 . . . . 177.47(16) ?
C12 N14 C26 C21 . . . . 0.15(15) ?
C24 C25 C26 N14 . . . . -176.25(16) ?
C24 C25 C26 C21 . . . . 0.7(2) ?
N13 C21 C26 N14 . . . . -0.14(16) ?
C22 C21 C26 N14 . . . . 177.20(13) ?
N13 C21 C26 C25 . . . . -177.82(14) ?
C22 C21 C26 C25 . . . . -0.5(2) ?
N1 C2 O31 C32 . . . . -0.87(19) ?
C3 C2 O31 C32 . . . . 178.30(13) ?
C2 O31 C32 C33 . . . . -177.84(12) ?
O31 C32 C33 O34 . . . . -71.36(16) ?
C32 C33 O34 C35 . . . . 153.87(13) ?
C33 O34 C35 C36 . . . . -78.72(17) ?
O34 C35 C36 O37 . . . . -53.58(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741641
