#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225678.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_2225678
loop_
_publ_author_name
'Wang, Chao-Hsiang'
'Liu, Yi-Chang'
'Lin, Chia-Her'
'Ko, Bao-Tsan'
_publ_section_title
;
 (E)-N-{2-[1-(Benzylimino)ethyl]phenyl}benzamide
;
_journal_coeditor_code           RK2194
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o745
_journal_paper_doi               10.1107/S1600536810007610
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H20 N2 O'
_chemical_formula_moiety         'C22 H20 N2 O'
_chemical_formula_sum            'C22 H20 N2 O'
_chemical_formula_weight         328.40
_chemical_name_systematic
;
(E)-N-{2-[1-(Benzylimino)ethyl]phenyl}benzamide
;
_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                 114.394(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4213(4)
_cell_length_b                   17.0799(7)
_cell_length_c                   10.8028(5)
_cell_measurement_reflns_used    1657
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.330
_cell_measurement_theta_min      1.66
_cell_volume                     1751.18(13)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_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      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20052
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0531
_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)+(0.0710P)²+0.1853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1609
_reflns_number_gt                2414
_reflns_number_total             4263
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rk2194.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225678
_cod_database_fobs_code          2225678
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 0.81960(13) 0.10603(8) 0.23208(15) 0.0812(4) Uani d . 1 . .
N N1 0.34187(14) 0.01877(8) 0.15594(15) 0.0574(4) Uani d . 1 . .
N N2 0.60695(13) 0.06148(8) 0.21381(14) 0.0539(4) Uani d . 1 . .
H H2B 0.5180 0.0649 0.1640 0.065 Uiso calc R 1 . .
C C1 0.1425(2) 0.16265(13) 0.0401(2) 0.0861(6) Uani d . 1 . .
H H1A 0.1731 0.1658 0.1339 0.103 Uiso calc R 1 . .
C C2 0.0954(3) 0.22894(14) -0.0374(3) 0.1020(8) Uani d . 1 . .
H H2A 0.0960 0.2765 0.0047 0.122 Uiso calc R 1 . .
C C3 0.0482(2) 0.22600(14) -0.1736(3) 0.0894(7) Uani d . 1 . .
H H3A 0.0147 0.2710 -0.2255 0.107 Uiso calc R 1 . .
C C4 0.0501(2) 0.15672(16) -0.2343(2) 0.0881(7) Uani d . 1 . .
H H4A 0.0183 0.1543 -0.3283 0.106 Uiso calc R 1 . .
C C5 0.09905(19) 0.08970(12) -0.1574(2) 0.0710(5) Uani d . 1 . .
H H5A 0.1006 0.0427 -0.2003 0.085 Uiso calc R 1 . .
C C6 0.14522(16) 0.09148(10) -0.01899(19) 0.0572(4) Uani d . 1 . .
C C7 0.19123(18) 0.01887(11) 0.0651(2) 0.0694(5) Uani d . 1 . .
H H7A 0.1371 0.0135 0.1191 0.083 Uiso calc R 1 . .
H H7B 0.1708 -0.0261 0.0051 0.083 Uiso calc R 1 . .
C C8 0.2975(2) -0.09913(11) 0.2593(2) 0.0810(6) Uani d . 1 . .
H H8A 0.2029 -0.0924 0.1920 0.122 Uiso calc R 1 . .
H H8B 0.2981 -0.0969 0.3484 0.122 Uiso calc R 1 . .
H H8C 0.3330 -0.1490 0.2468 0.122 Uiso calc R 1 . .
C C9 0.38926(17) -0.03509(9) 0.24489(18) 0.0539(4) Uani d . 1 . .
C C10 0.54103(17) -0.03557(9) 0.34125(17) 0.0528(4) Uani d . 1 . .
C C11 0.5834(2) -0.08470(11) 0.4543(2) 0.0687(5) Uani d . 1 . .
H H11A 0.5159 -0.1155 0.4664 0.082 Uiso calc R 1 . .
C C12 0.7205(2) -0.08954(13) 0.5482(2) 0.0807(6) Uani d . 1 . .
H H12A 0.7449 -0.1231 0.6222 0.097 Uiso calc R 1 . .
C C13 0.8209(2) -0.04467(14) 0.5322(2) 0.0804(6) Uani d . 1 . .
H H13A 0.9141 -0.0478 0.5954 0.096 Uiso calc R 1 . .
C C14 0.78470(19) 0.00524(11) 0.4231(2) 0.0684(5) Uani d . 1 . .
H H14A 0.8540 0.0359 0.4139 0.082 Uiso calc R 1 . .
C C15 0.64589(17) 0.01073(9) 0.32591(17) 0.0519(4) Uani d . 1 . .
C C16 0.69092(17) 0.10573(9) 0.17378(18) 0.0551(4) Uani d . 1 . .
C C17 0.61755(17) 0.15684(9) 0.05235(18) 0.0524(4) Uani d . 1 . .
C C18 0.6931(2) 0.21764(12) 0.0312(2) 0.0797(6) Uani d . 1 . .
H H18A 0.7863 0.2253 0.0921 0.096 Uiso calc R 1 . .
C C19 0.6337(3) 0.26723(13) -0.0778(3) 0.0901(7) Uani d . 1 . .
H H19A 0.6864 0.3082 -0.0893 0.108 Uiso calc R 1 . .
C C20 0.4985(2) 0.25675(12) -0.1688(2) 0.0795(6) Uani d . 1 . .
H H20A 0.4584 0.2902 -0.2428 0.095 Uiso calc R 1 . .
C C21 0.4218(2) 0.19642(14) -0.1506(2) 0.0801(6) Uani d . 1 . .
H H21A 0.3294 0.1886 -0.2132 0.096 Uiso calc R 1 . .
C C22 0.48016(18) 0.14713(11) -0.0403(2) 0.0674(5) Uani d . 1 . .
H H22A 0.4262 0.1069 -0.0284 0.081 Uiso calc R 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 N1 C7 . . 118.67(14) ?
C16 N2 C15 . . 128.61(14) ?
C16 N2 H2B . . 115.7 ?
C15 N2 H2B . . 115.7 ?
C2 C1 C6 . . 121.0(2) ?
C2 C1 H1A . . 119.5 ?
C6 C1 H1A . . 119.5 ?
C3 C2 C1 . . 120.9(2) ?
C3 C2 H2A . . 119.6 ?
C1 C2 H2A . . 119.6 ?
C2 C3 C4 . . 119.3(2) ?
C2 C3 H3A . . 120.3 ?
C4 C3 H3A . . 120.3 ?
C3 C4 C5 . . 120.4(2) ?
C3 C4 H4A . . 119.8 ?
C5 C4 H4A . . 119.8 ?
C6 C5 C4 . . 121.0(2) ?
C6 C5 H5A . . 119.5 ?
C4 C5 H5A . . 119.5 ?
C5 C6 C1 . . 117.39(18) ?
C5 C6 C7 . . 121.67(18) ?
C1 C6 C7 . . 120.88(19) ?
N1 C7 C6 . . 113.17(14) ?
N1 C7 H7A . . 108.9 ?
C6 C7 H7A . . 108.9 ?
N1 C7 H7B . . 108.9 ?
C6 C7 H7B . . 108.9 ?
H7A C7 H7B . . 107.8 ?
C9 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C9 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C10 . . 119.97(14) ?
N1 C9 C8 . . 122.63(16) ?
C10 C9 C8 . . 117.40(15) ?
C11 C10 C15 . . 117.31(16) ?
C11 C10 C9 . . 118.39(15) ?
C15 C10 C9 . . 124.30(15) ?
C12 C11 C10 . . 122.73(18) ?
C12 C11 H11A . . 118.6 ?
C10 C11 H11A . . 118.6 ?
C13 C12 C11 . . 119.44(19) ?
C13 C12 H12A . . 120.3 ?
C11 C12 H12A . . 120.3 ?
C12 C13 C14 . . 120.24(19) ?
C12 C13 H13A . . 119.9 ?
C14 C13 H13A . . 119.9 ?
C13 C14 C15 . . 121.23(18) ?
C13 C14 H14A . . 119.4 ?
C15 C14 H14A . . 119.4 ?
C14 C15 N2 . . 122.02(15) ?
C14 C15 C10 . . 119.03(16) ?
N2 C15 C10 . . 118.95(14) ?
O1 C16 N2 . . 123.57(16) ?
O1 C16 C17 . . 120.22(15) ?
N2 C16 C17 . . 116.21(14) ?
C22 C17 C18 . . 117.66(17) ?
C22 C17 C16 . . 124.64(15) ?
C18 C17 C16 . . 117.69(16) ?
C19 C18 C17 . . 121.37(19) ?
C19 C18 H18A . . 119.3 ?
C17 C18 H18A . . 119.3 ?
C20 C19 C18 . . 120.40(19) ?
C20 C19 H19A . . 119.8 ?
C18 C19 H19A . . 119.8 ?
C19 C20 C21 . . 119.3(2) ?
C19 C20 H20A . . 120.4 ?
C21 C20 H20A . . 120.4 ?
C20 C21 C22 . . 120.6(2) ?
C20 C21 H21A . . 119.7 ?
C22 C21 H21A . . 119.7 ?
C17 C22 C21 . . 120.66(17) ?
C17 C22 H22A . . 119.7 ?
C21 C22 H22A . . 119.7 ?
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 C16 . 1.2237(19) ?
N1 C9 . 1.273(2) ?
N1 C7 . 1.468(2) ?
N2 C16 . 1.355(2) ?
N2 C15 . 1.406(2) ?
N2 H2B . 0.8600 ?
C1 C2 . 1.373(3) ?
C1 C6 . 1.379(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.346(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.357(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.382(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.369(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.494(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.503(2) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.492(2) ?
C10 C11 . 1.394(2) ?
C10 C15 . 1.413(2) ?
C11 C12 . 1.371(3) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.364(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.375(3) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.396(2) ?
C14 H14A . 0.9300 ?
C16 C17 . 1.496(2) ?
C17 C22 . 1.377(2) ?
C17 C18 . 1.378(2) ?
C18 C19 . 1.373(3) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.356(3) ?
C19 H19A . 0.9300 ?
C20 C21 . 1.367(3) ?
C20 H20A . 0.9300 ?
C21 C22 . 1.378(3) ?
C21 H21A . 0.9300 ?
C22 H22A . 0.9300 ?
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 H2B N1 . 0.86 1.966 2.670(2) 138
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
C6 C1 C2 C3 . . . . 1.1(4) ?
C1 C2 C3 C4 . . . . -1.3(4) ?
C2 C3 C4 C5 . . . . 0.4(3) ?
C3 C4 C5 C6 . . . . 0.6(3) ?
C4 C5 C6 C1 . . . . -0.8(3) ?
C4 C5 C6 C7 . . . . 176.70(17) ?
C2 C1 C6 C5 . . . . -0.1(3) ?
C2 C1 C6 C7 . . . . -177.6(2) ?
C9 N1 C7 C6 . . . . 170.89(16) ?
C5 C6 C7 N1 . . . . 114.16(19) ?
C1 C6 C7 N1 . . . . -68.4(2) ?
C7 N1 C9 C10 . . . . -178.33(15) ?
C7 N1 C9 C8 . . . . 0.8(3) ?
N1 C9 C10 C11 . . . . 166.75(16) ?
C8 C9 C10 C11 . . . . -12.5(2) ?
N1 C9 C10 C15 . . . . -13.2(2) ?
C8 C9 C10 C15 . . . . 167.56(16) ?
C15 C10 C11 C12 . . . . -0.3(3) ?
C9 C10 C11 C12 . . . . 179.70(17) ?
C10 C11 C12 C13 . . . . 0.2(3) ?
C11 C12 C13 C14 . . . . 0.3(3) ?
C12 C13 C14 C15 . . . . -0.7(3) ?
C13 C14 C15 N2 . . . . 179.93(17) ?
C13 C14 C15 C10 . . . . 0.5(3) ?
C16 N2 C15 C14 . . . . 6.6(3) ?
C16 N2 C15 C10 . . . . -174.05(15) ?
C11 C10 C15 C14 . . . . -0.1(2) ?
C9 C10 C15 C14 . . . . 179.92(15) ?
C11 C10 C15 N2 . . . . -179.47(14) ?
C9 C10 C15 N2 . . . . 0.5(2) ?
C15 N2 C16 O1 . . . . 1.6(3) ?
C15 N2 C16 C17 . . . . -177.54(14) ?
O1 C16 C17 C22 . . . . 162.53(18) ?
N2 C16 C17 C22 . . . . -18.3(2) ?
O1 C16 C17 C18 . . . . -17.0(3) ?
N2 C16 C17 C18 . . . . 162.18(17) ?
C22 C17 C18 C19 . . . . 0.4(3) ?
C16 C17 C18 C19 . . . . 179.96(19) ?
C17 C18 C19 C20 . . . . -0.8(4) ?
C18 C19 C20 C21 . . . . 0.2(4) ?
C19 C20 C21 C22 . . . . 0.7(3) ?
C18 C17 C22 C21 . . . . 0.6(3) ?
C16 C17 C22 C21 . . . . -178.98(17) ?
C20 C21 C22 C17 . . . . -1.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744612
