#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/68/2226864.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_2226864
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Braley, Adam N.'
'Samshuddin, S.'
'Narayana, B.'
'Yathirajan, H. S.'
_publ_section_title
;
 4-(1H-Benzimidazol-2-ylmethoxy)-3-ethoxybenzaldehyde trihydrate
;
_journal_coeditor_code           FL2307
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2052
_journal_paper_doi               10.1107/S1600536810027455
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H16 N2 O3, 3H2 O'
_chemical_formula_moiety         'C17 H16 N2 O3, 3(H2 O)'
_chemical_formula_sum            'C17 H22 N2 O6'
_chemical_formula_weight         350.37
_chemical_name_systematic
;
4-(1H-Benzimidazol-2-ylmethoxy)-3-ethoxybenzaldehyde trihydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3020(15)
_cell_length_b                   9.3170(19)
_cell_length_c                   25.950(5)
_cell_measurement_reflns_used    3976
_cell_measurement_temperature    100
_cell_measurement_theta_max      77.1800
_cell_measurement_theta_min      4.7423
_cell_volume                     1765.4(6)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur with a Ruby (Gemini CCD) detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            4635
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         77.38
_diffrn_reflns_theta_min         5.85
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisRED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.160
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0683P)²+0.1610P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1021
_reflns_number_gt                2030
_reflns_number_total             2130
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2307.cif
_cod_data_source_block           I
_cod_database_code               2226864
_cod_database_fobs_code          2226864
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 O1 0.1649(2) 0.05517(14) 0.09028(5) 0.0436(3) Uani d . 1 . .
N N1 0.1237(2) 0.36636(17) -0.10832(5) 0.0413(4) Uani d . 1 . .
C C1 0.1274(2) 0.1882(2) 0.10989(6) 0.0380(4) Uani d . 1 . .
O O2 0.1203(3) 0.3165(3) 0.26729(6) 0.0857(7) Uani d . 1 . .
N N2 0.0561(2) 0.15054(16) -0.07628(5) 0.0400(3) Uani d . 1 . .
H H2A 0.0291 0.0857 -0.0539 0.048 Uiso calc R 1 . .
C C2 0.0862(2) 0.2957(2) 0.07342(6) 0.0368(4) Uani d . 1 . .
O O3 0.0958(2) 0.25276(13) 0.02315(4) 0.0436(3) Uani d . 1 . .
C C3 0.0434(3) 0.4335(2) 0.08910(7) 0.0443(4) Uani d . 1 . .
H H3 0.0156 0.5040 0.0650 0.053 Uiso calc R 1 . .
C C4 0.0424(3) 0.4653(2) 0.14156(8) 0.0501(5) Uani d . 1 . .
H H4 0.0121 0.5574 0.1524 0.060 Uiso calc R 1 . .
C C5 0.0857(3) 0.3622(3) 0.17741(7) 0.0483(5) Uani d . 1 . .
C C6 0.1279(3) 0.2223(2) 0.16162(7) 0.0441(4) Uani d . 1 . .
H H6 0.1561 0.1525 0.1860 0.053 Uiso calc R 1 . .
C C7 0.2193(3) -0.0543(2) 0.12644(8) 0.0484(5) Uani d . 1 . .
H H7A 0.1208 -0.0732 0.1506 0.058 Uiso calc R 1 . .
H H7B 0.3260 -0.0231 0.1457 0.058 Uiso calc R 1 . .
C C8 0.2631(4) -0.1874(2) 0.09646(11) 0.0656(7) Uani d . 1 . .
H H8A 0.1546 -0.2210 0.0794 0.098 Uiso calc R 1 . .
H H8B 0.3073 -0.2602 0.1195 0.098 Uiso calc R 1 . .
H H8C 0.3554 -0.1661 0.0713 0.098 Uiso calc R 1 . .
C C9 0.0857(4) 0.3982(3) 0.23244(9) 0.0662(7) Uani d . 1 . .
H H9 0.0565 0.4922 0.2413 0.079 Uiso calc R 1 . .
C C10 0.0577(3) 0.35874(19) -0.01518(6) 0.0408(4) Uani d . 1 . .
H H10A 0.1400 0.4397 -0.0112 0.049 Uiso calc R 1 . .
H H10B -0.0671 0.3930 -0.0115 0.049 Uiso calc R 1 . .
C C11 0.0832(2) 0.29187(19) -0.06693(6) 0.0369(4) Uani d . 1 . .
C C12 0.1204(3) 0.2666(2) -0.14792(7) 0.0408(4) Uani d . 1 . .
C C13 0.0800(2) 0.1305(2) -0.12853(7) 0.0411(4) Uani d . 1 . .
C C14 0.0735(3) 0.0092(3) -0.15962(9) 0.0543(5) Uani d . 1 . .
H H14 0.0505 -0.0814 -0.1461 0.065 Uiso calc R 1 . .
C C15 0.1030(3) 0.0301(3) -0.21162(9) 0.0644(6) Uani d . 1 . .
H H15 0.1000 -0.0484 -0.2337 0.077 Uiso calc R 1 . .
C C16 0.1372(4) 0.1668(3) -0.23188(8) 0.0655(7) Uani d . 1 . .
H H16 0.1525 0.1772 -0.2673 0.079 Uiso calc R 1 . .
C C17 0.1488(3) 0.2858(3) -0.20093(7) 0.0541(5) Uani d . 1 . .
H H17 0.1746 0.3759 -0.2146 0.065 Uiso calc R 1 . .
O O1W -0.0115(3) -0.06193(16) -0.00113(5) 0.0539(4) Uani d D 1 . .
H H1W1 -0.080(4) -0.128(3) 0.0094(11) 0.081 Uiso d D 1 . .
H H1W2 0.025(4) -0.027(3) 0.0264(9) 0.081 Uiso d D 1 . .
O O2W 0.2184(4) 0.65334(19) -0.13309(7) 0.0814(7) Uani d D 1 . .
H H2W1 0.266(5) 0.660(4) -0.1614(10) 0.122 Uiso d D 1 . .
H H2W2 0.206(6) 0.569(2) -0.1259(15) 0.122 Uiso d D 1 . .
O O3W 0.2942(3) 0.7793(2) -0.04092(7) 0.0720(5) Uani d D 1 . .
H H3W1 0.272(5) 0.749(4) -0.0708(9) 0.108 Uiso d D 1 . .
H H3W2 0.198(4) 0.820(4) -0.0315(13) 0.108 Uiso d 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O1 C7 . . 117.02(14) ?
C11 N1 C12 . . 104.39(15) ?
O1 C1 C6 . . 124.79(17) ?
O1 C1 C2 . . 115.88(14) ?
C6 C1 C2 . . 119.33(17) ?
C11 N2 C13 . . 106.84(15) ?
C11 N2 H2A . . 126.6 ?
C13 N2 H2A . . 126.6 ?
O3 C2 C3 . . 124.35(16) ?
O3 C2 C1 . . 114.97(15) ?
C3 C2 C1 . . 120.67(16) ?
C2 O3 C10 . . 116.91(14) ?
C2 C3 C4 . . 119.09(18) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C5 C4 C3 . . 120.76(19) ?
C5 C4 H4 . . 119.6 ?
C3 C4 H4 . . 119.6 ?
C4 C5 C6 . . 120.21(17) ?
C4 C5 C9 . . 119.9(2) ?
C6 C5 C9 . . 119.8(2) ?
C1 C6 C5 . . 119.92(19) ?
C1 C6 H6 . . 120.0 ?
C5 C6 H6 . . 120.0 ?
O1 C7 C8 . . 107.84(16) ?
O1 C7 H7A . . 110.1 ?
C8 C7 H7A . . 110.1 ?
O1 C7 H7B . . 110.1 ?
C8 C7 H7B . . 110.1 ?
H7A C7 H7B . . 108.5 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O2 C9 C5 . . 125.8(3) ?
O2 C9 H9 . . 117.1 ?
C5 C9 H9 . . 117.1 ?
O3 C10 C11 . . 108.28(14) ?
O3 C10 H10A . . 110.0 ?
C11 C10 H10A . . 110.0 ?
O3 C10 H10B . . 110.0 ?
C11 C10 H10B . . 110.0 ?
H10A C10 H10B . . 108.4 ?
N1 C11 N2 . . 113.62(16) ?
N1 C11 C10 . . 122.95(16) ?
N2 C11 C10 . . 123.31(15) ?
N1 C12 C13 . . 110.22(15) ?
N1 C12 C17 . . 129.7(2) ?
C13 C12 C17 . . 120.0(2) ?
N2 C13 C14 . . 132.61(19) ?
N2 C13 C12 . . 104.93(16) ?
C14 C13 C12 . . 122.45(17) ?
C15 C14 C13 . . 116.6(2) ?
C15 C14 H14 . . 121.7 ?
C13 C14 H14 . . 121.7 ?
C14 C15 C16 . . 121.5(2) ?
C14 C15 H15 . . 119.2 ?
C16 C15 H15 . . 119.2 ?
C17 C16 C15 . . 121.76(19) ?
C17 C16 H16 . . 119.1 ?
C15 C16 H16 . . 119.1 ?
C16 C17 C12 . . 117.5(2) ?
C16 C17 H17 . . 121.2 ?
C12 C17 H17 . . 121.2 ?
H1W1 O1W H1W2 . . 102(2) ?
H2W1 O2W H2W2 . . 109(3) ?
H3W1 O3W H3W2 . . 105(3) ?
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 C1 . 1.367(2) ?
O1 C7 . 1.442(2) ?
N1 C11 . 1.313(2) ?
N1 C12 . 1.386(2) ?
C1 C6 . 1.380(2) ?
C1 C2 . 1.410(2) ?
O2 C9 . 1.209(4) ?
N2 C11 . 1.354(2) ?
N2 C13 . 1.380(2) ?
N2 H2A . 0.8600 ?
C2 O3 . 1.3660(19) ?
C2 C3 . 1.383(3) ?
O3 C10 . 1.429(2) ?
C3 C4 . 1.393(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.374(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.400(3) ?
C5 C9 . 1.467(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.498(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9 . 0.9300 ?
C10 C11 . 1.492(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C12 C13 . 1.397(3) ?
C12 C17 . 1.402(2) ?
C13 C14 . 1.389(3) ?
C14 C15 . 1.380(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.400(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.372(4) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
O1W H1W1 . 0.840(17) ?
O1W H1W2 . 0.829(17) ?
O2W H2W1 . 0.815(18) ?
O2W H2W2 . 0.809(19) ?
O3W H3W1 . 0.842(18) ?
O3W H3W2 . 0.832(18) ?
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
N2 H2A O1W . 0.86 1.96 2.822(2) 175.3
O1W H1W1 O3W 4_455 0.840(17) 1.869(18) 2.703(2) 171(3)
O1W H1W2 O1 . 0.829(17) 2.092(18) 2.911(2) 170(3)
O2W H2W1 O2 2_564 0.815(18) 2.040(18) 2.855(2) 178(4)
O2W H2W2 N1 . 0.809(19) 2.04(2) 2.836(3) 169(5)
O3W H3W1 O2W . 0.842(18) 1.886(19) 2.721(3) 171(4)
O3W H3W2 O1W 1_565 0.832(18) 2.045(18) 2.870(3) 171(4)
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 O1 C1 C6 . . . . -3.9(3) ?
C7 O1 C1 C2 . . . . 175.99(16) ?
O1 C1 C2 O3 . . . . -2.2(2) ?
C6 C1 C2 O3 . . . . 177.71(16) ?
O1 C1 C2 C3 . . . . 178.95(16) ?
C6 C1 C2 C3 . . . . -1.1(3) ?
C3 C2 O3 C10 . . . . -0.3(3) ?
C1 C2 O3 C10 . . . . -179.14(16) ?
O3 C2 C3 C4 . . . . -178.37(18) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C2 C3 C4 C5 . . . . 0.9(3) ?
C3 C4 C5 C6 . . . . -1.3(3) ?
C3 C4 C5 C9 . . . . 179.4(2) ?
O1 C1 C6 C5 . . . . -179.41(18) ?
C2 C1 C6 C5 . . . . 0.7(3) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C9 C5 C6 C1 . . . . 179.83(19) ?
C1 O1 C7 C8 . . . . -176.90(18) ?
C4 C5 C9 O2 . . . . 179.5(3) ?
C6 C5 C9 O2 . . . . 0.2(4) ?
C2 O3 C10 C11 . . . . 177.64(15) ?
C12 N1 C11 N2 . . . . 0.8(2) ?
C12 N1 C11 C10 . . . . -175.35(17) ?
C13 N2 C11 N1 . . . . -0.3(2) ?
C13 N2 C11 C10 . . . . 175.87(16) ?
O3 C10 C11 N1 . . . . -154.73(17) ?
O3 C10 C11 N2 . . . . 29.4(2) ?
C11 N1 C12 C13 . . . . -1.1(2) ?
C11 N1 C12 C17 . . . . 178.2(2) ?
C11 N2 C13 C14 . . . . 178.3(2) ?
C11 N2 C13 C12 . . . . -0.4(2) ?
N1 C12 C13 N2 . . . . 0.9(2) ?
C17 C12 C13 N2 . . . . -178.49(18) ?
N1 C12 C13 C14 . . . . -177.95(18) ?
C17 C12 C13 C14 . . . . 2.7(3) ?
N2 C13 C14 C15 . . . . 179.3(2) ?
C12 C13 C14 C15 . . . . -2.2(3) ?
C13 C14 C15 C16 . . . . -0.1(4) ?
C14 C15 C16 C17 . . . . 2.1(4) ?
C15 C16 C17 C12 . . . . -1.6(4) ?
N1 C12 C17 C16 . . . . -179.9(2) ?
C13 C12 C17 C16 . . . . -0.7(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656153
