#------------------------------------------------------------------------------
#$Date: 2023-02-07 11:53:08 +0200 (Tue, 07 Feb 2023) $
#$Revision: 280804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106704.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106704
loop_
_publ_author_name
'Yang, Yu-Hua'
'Akogun, Sunday Folaranmi'
'Dong, Wen-Kui'
_publ_section_title
;
 Crystal structure of
 (E)-1-(2-hydroxy-3-{[2-hydroxybenzylidene]amino}phenyl)ethan-1-one,
 C15H13NO3
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              867
_journal_page_last               868
_journal_paper_doi               10.1515/ncrs-2017-0033
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.243(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5158(6)
_cell_length_b                   6.3940(5)
_cell_length_c                   25.881(3)
_cell_measurement_reflns_used    1032
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.5810
_cell_measurement_theta_min      3.9580
_cell_volume                     1241.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   16.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000   30.0000 20

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   90.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   19.0000   90.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega   18.00   91.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000  150.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0587301000
_diffrn_orient_matrix_UB_12      0.0329981000
_diffrn_orient_matrix_UB_13      0.0208294000
_diffrn_orient_matrix_UB_21      0.0704525000
_diffrn_orient_matrix_UB_22      0.0068278000
_diffrn_orient_matrix_UB_23      -0.0170391000
_diffrn_orient_matrix_UB_31      -0.0228048000
_diffrn_orient_matrix_UB_32      0.1057338000
_diffrn_orient_matrix_UB_33      -0.0053780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4274
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.56
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0547
_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)+(0.0639P)²+0.2288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1582
_reflns_number_gt                1626
_reflns_number_total             2430
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0033_suppl.cif
_cod_data_source_block           d645
_cod_original_cell_volume        1241.74(19)
_cod_database_code               8106704
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.1617(2) 0.6715(3) 0.33013(6) 0.0451(5) Uani 1 d . . .
H1 H 0.2499 0.6836 0.3501 0.068 Uiso 1 calc . . GR
O2 O 0.38250(18) 0.7432(2) 0.45362(5) 0.0300(4) Uani 1 d . . .
H2A H 0.3615 0.7483 0.4843 0.045 Uiso 1 calc . . GR
O3 O 0.4504(2) 0.7575(2) 0.55070(6) 0.0347(4) Uani 1 d . . .
N1 N 0.4910(2) 0.7272(3) 0.35802(7) 0.0264(4) Uani 1 d . . .
C1 C 0.2100(3) 0.6927(4) 0.28098(8) 0.0323(5) Uani 1 d . . .
C2 C 0.0808(3) 0.6716(4) 0.24065(9) 0.0416(6) Uani 1 d . . .
H2 H -0.0363 0.6420 0.2478 0.050 Uiso 1 calc . . R
C3 C 0.1258(3) 0.6944(4) 0.19022(9) 0.0446(7) Uani 1 d . . .
H3 H 0.0378 0.6805 0.1637 0.053 Uiso 1 calc . . R
C4 C 0.2986(3) 0.7375(3) 0.17807(9) 0.0404(6) Uani 1 d . . .
H4 H 0.3271 0.7530 0.1438 0.048 Uiso 1 calc . . R
C5 C 0.4278(3) 0.7569(3) 0.21762(8) 0.0330(5) Uani 1 d . . .
H5 H 0.5446 0.7848 0.2097 0.040 Uiso 1 calc . . R
C6 C 0.3872(3) 0.7357(3) 0.26959(8) 0.0261(5) Uani 1 d . . .
C7 C 0.5255(3) 0.7525(3) 0.31029(8) 0.0269(5) Uani 1 d . . .
H7 H 0.6416 0.7821 0.3019 0.032 Uiso 1 calc . . R
C8 C 0.6227(3) 0.7349(3) 0.39886(8) 0.0246(5) Uani 1 d . . .
C9 C 0.5603(3) 0.7423(3) 0.44895(8) 0.0241(5) Uani 1 d . . .
C10 C 0.6816(3) 0.7503(3) 0.49268(8) 0.0259(5) Uani 1 d . . .
C11 C 0.8643(3) 0.7468(3) 0.48478(9) 0.0332(6) Uani 1 d . . .
H11 H 0.9458 0.7529 0.5131 0.040 Uiso 1 calc . . R
C12 C 0.9252(3) 0.7344(3) 0.43580(9) 0.0365(6) Uani 1 d . . .
H12 H 1.0470 0.7299 0.4313 0.044 Uiso 1 calc . . R
C13 C 0.8050(3) 0.7286(3) 0.39309(9) 0.0316(5) Uani 1 d . . .
H13 H 0.8474 0.7203 0.3601 0.038 Uiso 1 calc . . R
C14 C 0.6119(3) 0.7611(3) 0.54474(8) 0.0298(5) Uani 1 d . . .
C15 C 0.7390(3) 0.7770(4) 0.59150(9) 0.0413(6) Uani 1 d . . .
H15A H 0.8114 0.6534 0.5941 0.062 Uiso 1 calc . . GR
H15B H 0.6728 0.7904 0.6220 0.062 Uiso 1 calc . . GR
H15C H 0.8139 0.8974 0.5883 0.062 Uiso 1 calc . . GR
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_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O1 H1 109.5 . .
C9 O2 H2A 109.5 . .
C7 N1 C8 122.99(18) . .
O1 C1 C2 119.0(2) . .
O1 C1 C6 121.68(18) . .
C2 C1 C6 119.4(2) . .
C1 C2 H2 119.9 . .
C3 C2 C1 120.3(2) . .
C3 C2 H2 119.9 . .
C2 C3 H3 119.3 . .
C2 C3 C4 121.5(2) . .
C4 C3 H3 119.3 . .
C3 C4 H4 120.6 . .
C5 C4 C3 118.8(2) . .
C5 C4 H4 120.6 . .
C4 C5 H5 119.3 . .
C4 C5 C6 121.4(2) . .
C6 C5 H5 119.3 . .
C1 C6 C7 120.91(19) . .
C5 C6 C1 118.67(19) . .
C5 C6 C7 120.4(2) . .
N1 C7 C6 121.02(19) . .
N1 C7 H7 119.5 . .
C6 C7 H7 119.5 . .
C9 C8 N1 115.89(18) . .
C13 C8 N1 125.13(19) . .
C13 C8 C9 118.94(18) . .
O2 C9 C8 117.87(17) . .
O2 C9 C10 121.69(18) . .
C8 C9 C10 120.44(19) . .
C9 C10 C14 119.17(19) . .
C11 C10 C9 118.41(19) . .
C11 C10 C14 122.42(18) . .
C10 C11 H11 119.5 . .
C12 C11 C10 121.07(19) . .
C12 C11 H11 119.5 . .
C11 C12 H12 120.0 . .
C11 C12 C13 120.1(2) . .
C13 C12 H12 120.0 . .
C8 C13 C12 121.0(2) . .
C8 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
O3 C14 C10 121.10(18) . .
O3 C14 C15 119.1(2) . .
C10 C14 C15 119.8(2) . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.8200 .
O1 C1 1.349(2) .
O2 H2A 0.8200 .
O2 C9 1.349(2) .
O3 C14 1.233(3) .
N1 C7 1.287(3) .
N1 C8 1.408(3) .
C1 C2 1.391(3) .
C1 C6 1.407(3) .
C2 H2 0.9300 .
C2 C3 1.374(3) .
C3 H3 0.9300 .
C3 C4 1.381(3) .
C4 H4 0.9300 .
C4 C5 1.376(3) .
C5 H5 0.9300 .
C5 C6 1.403(3) .
C6 C7 1.442(3) .
C7 H7 0.9300 .
C8 C9 1.404(3) .
C8 C13 1.387(3) .
C9 C10 1.413(3) .
C10 C11 1.400(3) .
C10 C14 1.474(3) .
C11 H11 0.9300 .
C11 C12 1.374(3) .
C12 H12 0.9300 .
C12 C13 1.388(3) .
C13 H13 0.9300 .
C14 C15 1.502(3) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
