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#$Date: 2022-12-08 10:43:26 +0200 (Thu, 08 Dec 2022) $
#$Revision: 279803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106369.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_8106369
loop_
_publ_author_name
'Fu, Tao'
'Ma, Jin-Xia'
'Li, Qing-Lin'
'Wei, Ping'
'Zhao, Ji-Xing'
'Zhao, Li'
_publ_section_title
;
 Crystal structure of
 (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one
 O-methyl oxime, C16H14Cl2N2O2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              979
_journal_page_last               980
_journal_paper_doi               10.1515/ncrs-2017-0405
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C16 H14 Cl2 N2 O2'
_chemical_formula_sum            'C16 H14 Cl2 N2 O2'
_chemical_formula_weight         337.19
_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
_cell_angle_alpha                90
_cell_angle_beta                 103.651(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9157(6)
_cell_length_b                   13.4533(8)
_cell_length_c                   14.8459(10)
_cell_measurement_reflns_used    9713
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.58
_cell_measurement_theta_min      2.37
_cell_volume                     1536.31(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.495
_diffrn_reflns_theta_min         2.648
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description
;
;
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0410
_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)+(0.0583P)²+0.5204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2757
_reflns_number_total             3168
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0405_suppl.cif
_cod_data_source_block           1
_cod_database_code               8106369
_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_max   0.930
_shelx_estimated_absorpt_t_min   0.911
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C13(H13), C3(H3), C12(H12), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_shelxl_version_number     2017/1
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.24332(7) 0.22160(3) 0.14590(3) 0.03503(16) Uani 1 1 d . . . . .
Cl2 Cl 0.14421(7) -0.16966(3) 0.07978(3) 0.03444(16) Uani 1 1 d . . . . .
O1 O 0.49137(19) 0.15795(8) 0.31249(9) 0.0287(3) Uani 1 1 d . . . . .
H1 H 0.561644 0.136953 0.358252 0.043 Uiso 1 1 calc GR . . . .
C7 C 0.5685(2) -0.04118(12) 0.37640(11) 0.0239(4) Uani 1 1 d . . . . .
H7 H 0.587403 -0.107330 0.394091 0.029 Uiso 1 1 calc R . . . .
N2 N 1.1974(2) 0.04531(12) 0.81615(10) 0.0287(4) Uani 1 1 d . . . . .
C11 C 1.0063(2) -0.02266(13) 0.68669(11) 0.0234(4) Uani 1 1 d . . . . .
O2 O 1.32073(19) 0.02804(10) 0.89959(9) 0.0337(3) Uani 1 1 d . . . . .
C5 C 0.3653(2) -0.09510(12) 0.23222(11) 0.0240(4) Uani 1 1 d . . . . .
H5 H 0.388583 -0.160929 0.249979 0.029 Uiso 1 1 calc R . . . .
C1 C 0.4138(2) 0.08144(11) 0.26176(11) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.2930(2) 0.09937(12) 0.17812(11) 0.0225(4) Uani 1 1 d . . . . .
C6 C 0.4491(2) -0.01814(12) 0.28910(11) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.6488(2) 0.02689(10) 0.43001(9) 0.0230(3) Uani 1 1 d . . . . .
C14 C 1.1361(2) -0.03553(13) 0.77589(11) 0.0246(4) Uani 1 1 d . . . . .
C8 C 0.7659(2) 0.00524(12) 0.51566(11) 0.0223(4) Uani 1 1 d . . . . .
C4 C 0.2489(2) -0.07352(12) 0.15030(11) 0.0235(4) Uani 1 1 d . . . . .
C13 C 0.8484(3) 0.08568(13) 0.56588(12) 0.0291(4) Uani 1 1 d . . . . .
H13 H 0.824381 0.149581 0.542454 0.035 Uiso 1 1 calc R . . . .
C3 C 0.2099(2) 0.02362(12) 0.12210(11) 0.0231(4) Uani 1 1 d . . . . .
H3 H 0.129761 0.037462 0.066820 0.028 Uiso 1 1 calc R . . . .
C12 C 0.9653(3) 0.07256(13) 0.64981(12) 0.0302(4) Uani 1 1 d . . . . .
H12 H 1.017812 0.127764 0.682527 0.036 Uiso 1 1 calc R . . . .
C9 C 0.8022(3) -0.08943(13) 0.55294(12) 0.0310(4) Uani 1 1 d . . . . .
H9 H 0.746378 -0.144315 0.521144 0.037 Uiso 1 1 calc R . . . .
C10 C 0.9209(3) -0.10260(13) 0.63699(12) 0.0299(4) Uani 1 1 d . . . . .
H10 H 0.943869 -0.166495 0.660637 0.036 Uiso 1 1 calc R . . . .
C16 C 1.3795(3) 0.12249(15) 0.93907(13) 0.0366(5) Uani 1 1 d . . . . .
H16A H 1.424305 0.160614 0.895228 0.055 Uiso 1 1 calc GR . . . .
H16B H 1.469484 0.112788 0.994317 0.055 Uiso 1 1 calc GR . . . .
H16C H 1.284071 0.157453 0.954152 0.055 Uiso 1 1 calc GR . . . .
C15 C 1.1900(3) -0.13686(15) 0.81399(13) 0.0342(4) Uani 1 1 d . . . . .
H15A H 1.300134 -0.132507 0.858026 0.051 Uiso 1 1 calc GR . . . .
H15B H 1.200152 -0.180422 0.764317 0.051 Uiso 1 1 calc GR . . . .
H15C H 1.104296 -0.162554 0.844025 0.051 Uiso 1 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'
Cl Cl 0.1484 0.1585 '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 . .
C6 C7 H7 119.1 . .
N1 C7 H7 119.1 . .
N1 C7 C6 121.86(16) . .
C14 N2 O2 112.29(15) . .
C12 C11 C14 120.25(16) . .
C10 C11 C14 122.20(16) . .
C10 C11 C12 117.55(16) . .
N2 O2 C16 107.79(14) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
C4 C5 C6 120.10(15) . .
O1 C1 C2 119.66(14) . .
O1 C1 C6 122.46(16) . .
C2 C1 C6 117.88(15) . .
C1 C2 Cl1 118.19(13) . .
C3 C2 Cl1 119.32(13) . .
C3 C2 C1 122.47(15) . .
C5 C6 C7 119.90(15) . .
C5 C6 C1 119.73(16) . .
C1 C6 C7 120.36(15) . .
C7 N1 C8 122.36(15) . .
N2 C14 C11 115.11(16) . .
N2 C14 C15 123.63(17) . .
C11 C14 C15 121.26(16) . .
C13 C8 N1 116.60(15) . .
C13 C8 C9 118.26(17) . .
C9 C8 N1 125.14(16) . .
C5 C4 Cl2 119.95(13) . .
C5 C4 C3 121.51(15) . .
C3 C4 Cl2 118.53(13) . .
C8 C13 H13 119.4 . .
C12 C13 C8 121.14(16) . .
C12 C13 H13 119.4 . .
C2 C3 C4 118.30(16) . .
C2 C3 H3 120.8 . .
C4 C3 H3 120.8 . .
C11 C12 H12 119.5 . .
C13 C12 C11 121.01(17) . .
C13 C12 H12 119.5 . .
C8 C9 H9 119.7 . .
C10 C9 C8 120.54(17) . .
C10 C9 H9 119.7 . .
C11 C10 H10 119.3 . .
C9 C10 C11 121.47(16) . .
C9 C10 H10 119.3 . .
O2 C16 H16A 109.5 . .
O2 C16 H16B 109.5 . .
O2 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
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
Cl1 C2 1.7317(16) .
Cl2 C4 1.7453(17) .
O1 H1 0.8200 .
O1 C1 1.3361(19) .
C7 H7 0.9300 .
C7 C6 1.446(2) .
C7 N1 1.280(2) .
N2 O2 1.4036(19) .
N2 C14 1.280(2) .
C11 C14 1.482(2) .
C11 C12 1.401(2) .
C11 C10 1.386(3) .
O2 C16 1.430(2) .
C5 H5 0.9300 .
C5 C6 1.400(2) .
C5 C4 1.373(2) .
C1 C2 1.398(2) .
C1 C6 1.409(2) .
C2 C3 1.380(2) .
N1 C8 1.416(2) .
C14 C15 1.499(3) .
C8 C13 1.387(2) .
C8 C9 1.391(2) .
C4 C3 1.385(2) .
C13 H13 0.9300 .
C13 C12 1.377(3) .
C3 H3 0.9300 .
C12 H12 0.9300 .
C9 H9 0.9300 .
C9 C10 1.385(3) .
C10 H10 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Cl1 C2 C3 C4 -178.58(12) . . . .
Cl2 C4 C3 C2 179.99(12) . . . .
O1 C1 C2 Cl1 -2.3(2) . . . .
O1 C1 C2 C3 179.29(15) . . . .
O1 C1 C6 C7 2.2(2) . . . .
O1 C1 C6 C5 -179.11(15) . . . .
C7 N1 C8 C13 178.10(16) . . . .
C7 N1 C8 C9 -2.6(3) . . . .
O2 N2 C14 C11 -179.39(13) . . . .
O2 N2 C14 C15 0.1(2) . . . .
C5 C4 C3 C2 0.8(3) . . . .
C1 C2 C3 C4 -0.2(3) . . . .
C2 C1 C6 C7 -177.92(15) . . . .
C2 C1 C6 C5 0.7(2) . . . .
C6 C7 N1 C8 179.97(14) . . . .
C6 C5 C4 Cl2 -179.80(13) . . . .
C6 C5 C4 C3 -0.6(3) . . . .
C6 C1 C2 Cl1 177.84(12) . . . .
C6 C1 C2 C3 -0.6(2) . . . .
N1 C7 C6 C5 179.40(16) . . . .
N1 C7 C6 C1 -1.9(3) . . . .
N1 C8 C13 C12 -179.68(16) . . . .
N1 C8 C9 C10 179.20(16) . . . .
C14 N2 O2 C16 -179.51(15) . . . .
C14 C11 C12 C13 178.29(17) . . . .
C14 C11 C10 C9 -178.84(17) . . . .
C8 C13 C12 C11 0.8(3) . . . .
C8 C9 C10 C11 0.3(3) . . . .
C4 C5 C6 C7 178.49(15) . . . .
C4 C5 C6 C1 -0.2(3) . . . .
C13 C8 C9 C10 -1.5(3) . . . .
C12 C11 C14 N2 3.2(2) . . . .
C12 C11 C14 C15 -176.33(17) . . . .
C12 C11 C10 C9 1.4(3) . . . .
C9 C8 C13 C12 0.9(3) . . . .
C10 C11 C14 N2 -176.52(17) . . . .
C10 C11 C14 C15 3.9(3) . . . .
C10 C11 C12 C13 -2.0(3) . . . .
