#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229322.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_2229322
loop_
_publ_author_name
'Keypour, Hassan'
'Tamizi, Sareh'
'Dehghanpour, Saeed'
'Azadbakht, Reza'
'Khalaj, Mehdi'
_publ_section_title
;
 2-[1-(3-{2-[(2-Hydroxybenzylidene)amino]phenoxy}propyl)-1H-1,3-benzodiazol-2-yl]phenol
;
_journal_coeditor_code           BH2338
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o657
_journal_page_last               o658
_journal_paper_doi               10.1107/S1600536811005319
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C29 H25 N3 O3'
_chemical_formula_moiety         'C29 H25 N3 O3'
_chemical_formula_sum            'C29 H25 N3 O3'
_chemical_formula_weight         463.52
_chemical_name_systematic
;
2-[1-(3-{2-[(2-Hydroxybenzylidene)amino]phenoxy}propyl)-1H-
1,3-benzodiazol-2-yl]phenol
;
_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                 93.405(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1097(6)
_cell_length_b                   18.1946(11)
_cell_length_c                   13.7769(5)
_cell_measurement_reflns_used    16359
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     2279.5(2)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16359
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5135
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0553
_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)+(0.0536P)²+0.4485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                3083
_reflns_number_total             5135
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2338.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229322
_cod_database_fobs_code          2229322
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
O O1 0.98262(18) 0.22668(8) 0.88875(9) 0.0465(4) Uani d . 1 . .
H H1O 0.9212 0.1922 0.8864 0.070 Uiso calc R 1 . .
O O2 0.80830(16) 0.02045(7) 0.35975(9) 0.0369(4) Uani d . 1 . .
O O3 0.69646(17) -0.13681(8) 0.49252(9) 0.0418(4) Uani d . 1 . .
H H2O 0.7212 -0.1156 0.4418 0.063 Uiso calc R 1 . .
N N1 0.82575(18) 0.08636(9) 0.66217(11) 0.0352(4) Uani d . 1 . .
N N2 0.80517(19) 0.13040(9) 0.81279(11) 0.0378(4) Uani d . 1 . .
N N3 0.70199(18) -0.10938(9) 0.31140(11) 0.0323(4) Uani d . 1 . .
C C1 0.8674(2) 0.13987(11) 0.72906(13) 0.0348(5) Uani d U 1 . .
C C2 0.7258(2) 0.04118(11) 0.70695(14) 0.0355(5) Uani d . 1 . .
C C3 0.6454(2) -0.01894(12) 0.67220(16) 0.0424(5) Uani d . 1 . .
H H3A 0.6527 -0.0369 0.6079 0.051 Uiso calc R 1 . .
C C4 0.5538(2) -0.05139(12) 0.73642(17) 0.0461(6) Uani d . 1 . .
H H4A 0.4961 -0.0926 0.7155 0.055 Uiso calc R 1 . .
C C5 0.5439(2) -0.02520(12) 0.83139(17) 0.0462(6) Uani d . 1 . .
H H5A 0.4805 -0.0492 0.8736 0.055 Uiso calc R 1 . .
C C6 0.6241(2) 0.03446(12) 0.86451(16) 0.0428(5) Uani d . 1 . .
H H6A 0.6173 0.0520 0.9290 0.051 Uiso calc R 1 . .
C C7 0.7156(2) 0.06849(11) 0.80071(14) 0.0371(5) Uani d . 1 . .
C C8 0.9683(2) 0.20146(11) 0.71522(14) 0.0342(5) Uani d U 1 . .
C C9 1.0249(2) 0.24102(12) 0.79778(14) 0.0358(5) Uani d . 1 . .
C C10 1.1272(2) 0.29677(12) 0.78825(15) 0.0406(5) Uani d . 1 . .
H H10A 1.1682 0.3211 0.8445 0.049 Uiso calc R 1 . .
C C11 1.1694(2) 0.31703(12) 0.69784(16) 0.0433(5) Uani d . 1 . .
H H11A 1.2402 0.3549 0.6920 0.052 Uiso calc R 1 . .
C C12 1.1092(2) 0.28247(12) 0.61553(15) 0.0411(5) Uani d . 1 . .
H H12A 1.1353 0.2979 0.5530 0.049 Uiso calc R 1 . .
C C13 1.0116(2) 0.22574(11) 0.62434(14) 0.0375(5) Uani d . 1 . .
H H13A 0.9720 0.2021 0.5671 0.045 Uiso calc R 1 . .
C C14 0.8752(2) 0.07122(11) 0.56509(13) 0.0354(5) Uani d . 1 . .
H H14A 0.8771 0.0174 0.5545 0.042 Uiso calc R 1 . .
H H14B 0.9765 0.0900 0.5607 0.042 Uiso calc R 1 . .
C C15 0.7747(2) 0.10687(12) 0.48571(13) 0.0372(5) Uani d . 1 . .
H H15A 0.6749 0.0856 0.4877 0.045 Uiso calc R 1 . .
H H15B 0.7675 0.1602 0.4991 0.045 Uiso calc R 1 . .
C C16 0.8287(2) 0.09626(11) 0.38527(14) 0.0375(5) Uani d . 1 . .
H H16A 0.7725 0.1280 0.3380 0.045 Uiso calc R 1 . .
H H16B 0.9341 0.1095 0.3847 0.045 Uiso calc R 1 . .
C C17 0.8190(2) 0.00152(11) 0.26392(13) 0.0319(5) Uani d . 1 . .
C C18 0.8766(2) 0.04669(12) 0.19473(14) 0.0382(5) Uani d . 1 . .
H H18A 0.9154 0.0936 0.2127 0.046 Uiso calc R 1 . .
C C19 0.8774(2) 0.02298(12) 0.09868(15) 0.0420(5) Uani d . 1 . .
H H19A 0.9156 0.0542 0.0510 0.050 Uiso calc R 1 . .
C C20 0.8233(2) -0.04524(12) 0.07220(14) 0.0408(5) Uani d . 1 . .
H H20A 0.8249 -0.0611 0.0066 0.049 Uiso calc R 1 . .
C C21 0.7667(2) -0.09051(12) 0.14125(14) 0.0367(5) Uani d . 1 . .
H H21A 0.7311 -0.1379 0.1230 0.044 Uiso calc R 1 . .
C C22 0.7614(2) -0.06751(11) 0.23715(13) 0.0320(5) Uani d . 1 . .
C C23 0.5987(2) -0.15625(11) 0.29380(14) 0.0344(5) Uani d . 1 . .
H H23A 0.5604 -0.1634 0.2288 0.041 Uiso calc R 1 . .
C C24 0.5396(2) -0.19841(11) 0.37172(14) 0.0339(5) Uani d . 1 . .
C C25 0.4292(2) -0.25061(12) 0.35230(16) 0.0403(5) Uani d . 1 . .
H H25A 0.3930 -0.2584 0.2870 0.048 Uiso calc R 1 . .
C C26 0.3717(2) -0.29106(12) 0.42569(17) 0.0458(6) Uani d . 1 . .
H H26A 0.2965 -0.3263 0.4114 0.055 Uiso calc R 1 . .
C C27 0.4258(2) -0.27940(12) 0.52143(16) 0.0444(6) Uani d . 1 . .
H H27A 0.3875 -0.3073 0.5725 0.053 Uiso calc R 1 . .
C C28 0.5338(2) -0.22813(12) 0.54275(15) 0.0407(5) Uani d . 1 . .
H H28A 0.5687 -0.2206 0.6083 0.049 Uiso calc R 1 . .
C C29 0.5923(2) -0.18717(11) 0.46906(14) 0.0340(5) Uani 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
C9 O1 H1O . . 109.5 ?
C17 O2 C16 . . 117.50(14) ?
C29 O3 H2O . . 109.5 ?
C1 N1 C2 . . 106.32(16) ?
C1 N1 C14 . . 131.09(17) ?
C2 N1 C14 . . 122.48(16) ?
C1 N2 C7 . . 106.17(16) ?
C23 N3 C22 . . 122.11(16) ?
N2 C1 N1 . . 112.02(18) ?
N2 C1 C8 . . 121.00(17) ?
N1 C1 C8 . . 126.98(18) ?
C3 C2 C7 . . 122.6(2) ?
C3 C2 N1 . . 131.05(19) ?
C7 C2 N1 . . 106.32(18) ?
C4 C3 C2 . . 116.2(2) ?
C4 C3 H3A . . 121.9 ?
C2 C3 H3A . . 121.9 ?
C3 C4 C5 . . 121.8(2) ?
C3 C4 H4A . . 119.1 ?
C5 C4 H4A . . 119.1 ?
C6 C5 C4 . . 121.2(2) ?
C6 C5 H5A . . 119.4 ?
C4 C5 H5A . . 119.4 ?
C5 C6 C7 . . 118.0(2) ?
C5 C6 H6A . . 121.0 ?
C7 C6 H6A . . 121.0 ?
C6 C7 C2 . . 120.2(2) ?
C6 C7 N2 . . 130.68(19) ?
C2 C7 N2 . . 109.13(17) ?
C13 C8 C9 . . 116.56(19) ?
C13 C8 C1 . . 124.48(18) ?
C9 C8 C1 . . 118.95(18) ?
O1 C9 C10 . . 117.15(18) ?
O1 C9 C8 . . 122.22(19) ?
C10 C9 C8 . . 120.63(18) ?
C11 C10 C9 . . 120.45(19) ?
C11 C10 H10A . . 119.8 ?
C9 C10 H10A . . 119.8 ?
C10 C11 C12 . . 120.2(2) ?
C10 C11 H11A . . 119.9 ?
C12 C11 H11A . . 119.9 ?
C13 C12 C11 . . 119.8(2) ?
C13 C12 H12A . . 120.1 ?
C11 C12 H12A . . 120.1 ?
C12 C13 C8 . . 122.18(18) ?
C12 C13 H13A . . 118.9 ?
C8 C13 H13A . . 118.9 ?
N1 C14 C15 . . 111.78(16) ?
N1 C14 H14A . . 109.3 ?
C15 C14 H14A . . 109.3 ?
N1 C14 H14B . . 109.3 ?
C15 C14 H14B . . 109.3 ?
H14A C14 H14B . . 107.9 ?
C16 C15 C14 . . 112.85(17) ?
C16 C15 H15A . . 109.0 ?
C14 C15 H15A . . 109.0 ?
C16 C15 H15B . . 109.0 ?
C14 C15 H15B . . 109.0 ?
H15A C15 H15B . . 107.8 ?
O2 C16 C15 . . 107.68(16) ?
O2 C16 H16A . . 110.2 ?
C15 C16 H16A . . 110.2 ?
O2 C16 H16B . . 110.2 ?
C15 C16 H16B . . 110.2 ?
H16A C16 H16B . . 108.5 ?
O2 C17 C18 . . 124.33(18) ?
O2 C17 C22 . . 115.51(17) ?
C18 C17 C22 . . 120.12(17) ?
C17 C18 C19 . . 119.6(2) ?
C17 C18 H18A . . 120.2 ?
C19 C18 H18A . . 120.2 ?
C20 C19 C18 . . 120.6(2) ?
C20 C19 H19A . . 119.7 ?
C18 C19 H19A . . 119.7 ?
C19 C20 C21 . . 119.83(19) ?
C19 C20 H20A . . 120.1 ?
C21 C20 H20A . . 120.1 ?
C20 C21 C22 . . 120.7(2) ?
C20 C21 H21A . . 119.6 ?
C22 C21 H21A . . 119.6 ?
C21 C22 C17 . . 119.08(18) ?
C21 C22 N3 . . 124.35(18) ?
C17 C22 N3 . . 116.57(16) ?
N3 C23 C24 . . 120.85(18) ?
N3 C23 H23A . . 119.6 ?
C24 C23 H23A . . 119.6 ?
C25 C24 C29 . . 118.71(18) ?
C25 C24 C23 . . 120.85(18) ?
C29 C24 C23 . . 120.43(18) ?
C26 C25 C24 . . 121.5(2) ?
C26 C25 H25A . . 119.2 ?
C24 C25 H25A . . 119.2 ?
C25 C26 C27 . . 118.9(2) ?
C25 C26 H26A . . 120.6 ?
C27 C26 H26A . . 120.6 ?
C28 C27 C26 . . 120.9(2) ?
C28 C27 H27A . . 119.6 ?
C26 C27 H27A . . 119.6 ?
C27 C28 C29 . . 120.5(2) ?
C27 C28 H28A . . 119.7 ?
C29 C28 H28A . . 119.7 ?
O3 C29 C28 . . 119.03(18) ?
O3 C29 C24 . . 121.48(18) ?
C28 C29 C24 . . 119.48(19) ?
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 C9 . 1.358(2) ?
O1 H1O . 0.8400 ?
O2 C17 . 1.373(2) ?
O2 C16 . 1.433(2) ?
O3 C29 . 1.344(2) ?
O3 H2O . 0.8400 ?
N1 C1 . 1.378(2) ?
N1 C2 . 1.397(3) ?
N1 C14 . 1.462(2) ?
N2 C1 . 1.326(2) ?
N2 C7 . 1.395(3) ?
N3 C23 . 1.282(2) ?
N3 C22 . 1.409(2) ?
C1 C8 . 1.469(3) ?
C2 C3 . 1.386(3) ?
C2 C7 . 1.392(3) ?
C3 C4 . 1.384(3) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.400(3) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.371(3) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.392(3) ?
C6 H6A . 0.9500 ?
C8 C13 . 1.406(3) ?
C8 C9 . 1.417(3) ?
C9 C10 . 1.388(3) ?
C10 C11 . 1.376(3) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.381(3) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.372(3) ?
C12 H12A . 0.9500 ?
C13 H13A . 0.9500 ?
C14 C15 . 1.528(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 C16 . 1.508(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.385(3) ?
C17 C22 . 1.402(3) ?
C18 C19 . 1.392(3) ?
C18 H18A . 0.9500 ?
C19 C20 . 1.377(3) ?
C19 H19A . 0.9500 ?
C20 C21 . 1.381(3) ?
C20 H20A . 0.9500 ?
C21 C22 . 1.390(3) ?
C21 H21A . 0.9500 ?
C23 C24 . 1.449(3) ?
C23 H23A . 0.9500 ?
C24 C25 . 1.397(3) ?
C24 C29 . 1.412(3) ?
C25 C26 . 1.379(3) ?
C25 H25A . 0.9500 ?
C26 C27 . 1.397(3) ?
C26 H26A . 0.9500 ?
C27 C28 . 1.374(3) ?
C27 H27A . 0.9500 ?
C28 C29 . 1.391(3) ?
C28 H28A . 0.9500 ?
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
O1 H1O N2 . 0.84 1.81 2.564(2) 148 yes
O3 H2O N3 . 0.84 1.80 2.548(2) 148 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656510
