#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:28:40 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199126 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242151.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_2242151
loop_
_publ_author_name
'Reuter, Hans'
'Okio, Coco K. Y. A.'
_publ_section_title
;
 Crystal structure of (E)-2-hydroxy-1,2-diphenylethan-1-one oxime
;
_journal_coeditor_code           WM5397
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1062
_journal_page_last               1065
_journal_paper_doi               10.1107/S2056989017008866
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C14 H13 N O2'
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_name_systematic
;
(E)-2-Hydroxy-1,2-diphenylethan-1-one oxime
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.042(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.1434(9)
_cell_length_b                   10.5348(4)
_cell_length_c                   8.9006(4)
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.43
_cell_measurement_theta_min      3.08
_cell_volume                     2260.64(16)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al., 2006)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            50071
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.110
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.322
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0361P)²+2.1083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                1765
_reflns_number_total             2005
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5397sup1.cif
_cod_data_source_block           I
_cod_database_code               2242151
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.968
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_occupancy
O O1 0.43413(4) 0.17890(9) 0.80605(10) 0.0241(2) Uani d 1
H H1 0.4693 0.1776 0.8619 0.029(3) Uiso d 1
C C1 0.41037(6) 0.14256(12) 0.55975(15) 0.0203(3) Uani d 1
N N1 0.44993(5) 0.16404(11) 0.65751(12) 0.0214(3) Uani d 1
O O2 0.48687(4) 0.10235(9) 0.40164(11) 0.0252(3) Uani d 1
H H3 0.4938 0.0231 0.4524 0.029(3) Uiso d 0.5
H H4 0.4959 0.0973 0.2981 0.029(3) Uiso d 0.5
C C2 0.42878(6) 0.12695(13) 0.39955(15) 0.0217(3) Uani d 1
H H2 0.4086 0.0531 0.3519 0.029(3) Uiso calc 1
C C11 0.35015(6) 0.13354(13) 0.58375(15) 0.0210(3) Uani d 1
C C12 0.31705(6) 0.04617(14) 0.50248(16) 0.0253(3) Uani d 1
H H12 0.3332 -0.0072 0.4307 0.0306(19) Uiso calc 1
C C13 0.26100(6) 0.03627(15) 0.52511(17) 0.0302(4) Uani d 1
H H13 0.2391 -0.0245 0.4700 0.0306(19) Uiso calc 1
C C14 0.23671(6) 0.11432(16) 0.62737(17) 0.0311(4) Uani d 1
H H14 0.1982 0.1071 0.6432 0.0306(19) Uiso calc 1
C C15 0.26863(6) 0.20283(15) 0.70637(17) 0.0283(3) Uani d 1
H H15 0.2518 0.2576 0.7755 0.0306(19) Uiso calc 1
C C16 0.32497(6) 0.21281(14) 0.68598(16) 0.0247(3) Uani d 1
H H16 0.3466 0.2738 0.7417 0.0306(19) Uiso calc 1
C C21 0.41529(5) 0.24451(14) 0.30732(15) 0.0223(3) Uani d 1
C C22 0.43786(6) 0.36078(15) 0.34820(17) 0.0292(3) Uani d 1
H H22 0.4627 0.3671 0.4344 0.040(2) Uiso calc 1
C C23 0.42453(7) 0.46786(16) 0.2644(2) 0.0373(4) Uani d 1
H H23 0.4397 0.5478 0.2940 0.040(2) Uiso calc 1
C C24 0.38915(7) 0.45886(17) 0.13770(19) 0.0402(4) Uani d 1
H H24 0.3797 0.5327 0.0807 0.040(2) Uiso calc 1
C C25 0.36771(7) 0.34293(18) 0.09425(18) 0.0404(4) Uani d 1
H H25 0.3440 0.3362 0.0059 0.040(2) Uiso calc 1
C C26 0.38058(6) 0.23623(16) 0.17912(17) 0.0312(4) Uani d 1
H H26 0.3654 0.1564 0.1491 0.040(2) Uiso calc 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
_geom_angle_publ_flag
N1 O1 H1 102.1 ?
N1 C1 C11 128.03(12) ?
N1 C1 C2 114.30(10) yes
C11 C1 C2 117.70(10) yes
C1 N1 O1 115.50(10) yes
C2 O2 H3 108.1 ?
C2 O2 H4 105.7 ?
H3 O2 H4 111.2 ?
O2 C2 C21 109.84(11) ?
O2 C2 C1 110.10(10) yes
C21 C2 C1 110.75(11) ?
O2 C2 H2 108.7 ?
C21 C2 H2 108.7 ?
C1 C2 H2 108.7 ?
C12 C11 C16 118.33(13) ?
C12 C11 C1 120.41(12) ?
C16 C11 C1 121.26(13) ?
C13 C12 C11 120.81(13) ?
C13 C12 H12 119.6 ?
C11 C12 H12 119.6 ?
C14 C13 C12 120.31(14) ?
C14 C13 H13 119.8 ?
C12 C13 H13 119.8 ?
C15 C14 C13 119.58(14) ?
C15 C14 H14 120.2 ?
C13 C14 H14 120.2 ?
C14 C15 C16 120.70(14) ?
C14 C15 H15 119.6 ?
C16 C15 H15 119.6 ?
C15 C16 C11 120.25(14) ?
C15 C16 H16 119.9 ?
C11 C16 H16 119.9 ?
C22 C21 C26 119.12(14) ?
C22 C21 C2 120.85(13) ?
C26 C21 C2 120.02(13) ?
C23 C22 C21 120.32(15) ?
C23 C22 H22 119.8 ?
C21 C22 H22 119.8 ?
C22 C23 C24 120.07(16) ?
C22 C23 H23 120.0 ?
C24 C23 H23 120.0 ?
C25 C24 C23 119.88(15) ?
C25 C24 H24 120.1 ?
C23 C24 H24 120.1 ?
C24 C25 C26 119.95(16) ?
C24 C25 H25 120.0 ?
C26 C25 H25 120.0 ?
C25 C26 C21 120.62(16) ?
C25 C26 H26 119.7 ?
C21 C26 H26 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 1.4040(10) yes
O1 H1 0.9600 ?
C1 N1 1.278(2) yes
C1 C11 1.484(2) ?
C1 C2 1.525(2) yes
O2 C2 1.425(2) yes
O2 H3 0.9600 ?
O2 H4 0.9600 ?
C2 C21 1.512(2) ?
C2 H2 1.0000 ?
C11 C12 1.396(2) ?
C11 C16 1.398(2) ?
C12 C13 1.383(2) ?
C12 H12 0.9500 ?
C13 C14 1.380(2) ?
C13 H13 0.9500 ?
C14 C15 1.378(2) ?
C14 H14 0.9500 ?
C15 C16 1.386(2) ?
C15 H15 0.9500 ?
C16 H16 0.9500 ?
C21 C22 1.381(2) ?
C21 C26 1.382(2) ?
C22 C23 1.381(2) ?
C22 H22 0.9500 ?
C23 C24 1.382(3) ?
C23 H23 0.9500 ?
C24 C25 1.374(3) ?
C24 H24 0.9500 ?
C25 C26 1.380(2) ?
C25 H25 0.9500 ?
C26 H26 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
O1 H1 N1 2_656 0.96 1.97 2.805(2) 143.7
O2 H3 O2 5_656 0.96 1.89 2.829(2) 163.8
O2 H4 O2 2_655 0.96 1.85 2.806(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
C11 C1 N1 O1 1.1(2)
C2 C1 N1 O1 179.96(10)
N1 C1 C2 O2 17.34(16)
C11 C1 C2 O2 -163.64(11)
N1 C1 C2 C21 -104.31(14)
C11 C1 C2 C21 74.72(15)
N1 C1 C11 C12 -143.31(15)
C2 C1 C11 C12 37.82(18)
N1 C1 C11 C16 37.6(2)
C2 C1 C11 C16 -141.28(13)
C16 C11 C12 C13 -1.5(2)
C1 C11 C12 C13 179.39(13)
C11 C12 C13 C14 0.9(2)
C12 C13 C14 C15 0.3(2)
C13 C14 C15 C16 -1.1(2)
C14 C15 C16 C11 0.5(2)
C12 C11 C16 C15 0.8(2)
C1 C11 C16 C15 179.89(13)
O2 C2 C21 C22 -61.09(16)
C1 C2 C21 C22 60.68(16)
O2 C2 C21 C26 118.01(14)
C1 C2 C21 C26 -120.23(14)
C26 C21 C22 C23 1.9(2)
C2 C21 C22 C23 -178.96(13)
C21 C22 C23 C24 -1.0(2)
C22 C23 C24 C25 -0.7(2)
C23 C24 C25 C26 1.4(2)
C24 C25 C26 C21 -0.5(2)
C22 C21 C26 C25 -1.2(2)
C2 C21 C26 C25 179.69(13)

_cod_database_fobs_code 2242151
