#------------------------------------------------------------------------------
#$Date: 2022-04-01 10:36:57 +0300 (Fri, 01 Apr 2022) $
#$Revision: 274196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/49/8104983.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_8104983
loop_
_publ_author_name
'Jin, Ze-Sen'
'Liu, Xiao-jing'
'Liu, E.'
'Jian, Fang-fang'
'Liang, Tongling'
_publ_section_title
;
 Crystal structure of 2-((E)-(((E)-2-hydroxy-4-methylbenzylidene)
 hydrazineylidene)methyl)-4-methylphenol, C16H16N2O2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              141
_journal_page_last               142
_journal_paper_doi               10.1515/ncrs-2021-0411
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_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     dual
_cell_angle_alpha                90
_cell_angle_beta                 96.1660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.67660(10)
_cell_length_b                   5.90390(10)
_cell_length_c                   13.3603(2)
_cell_measurement_reflns_used    5821
_cell_measurement_temperature    169.98(11)
_cell_measurement_theta_max      74.6190
_cell_measurement_theta_min      5.0970
_cell_volume                     680.432(17)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.98(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -114.00 -61.00   0.50    0.15    --  -47.57 -16.00  47.00  106
  2  ω    -21.00   4.00   0.50    0.15    --  -47.57  16.00-142.00   50
  3  ω     40.00  79.00   0.50    0.15    --   47.57  16.00-142.00   78
  4  ω     -8.00  18.00   0.50    0.15    --   47.57 -16.00  47.00   52
  5  ω   -142.00-116.00   0.50    0.30    --  -99.00 -16.00  47.00   52
  6  ω     96.00 167.00   0.50    0.30    --  103.25  16.00-142.00  142
  7  ω    -74.00 -33.00   0.50    0.15    --  -47.57 -57.00 -60.00   82
  8  ω    -62.00 -37.00   0.50    0.15    --  -47.57 -19.00 -60.00   50
  9  ω    -77.00 -30.00   0.50    0.15    --  -47.57 -77.00 -90.00   94
 10  ω    -63.00 -25.00   0.50    0.15    --  -47.57 -77.00 -30.00   76
 11  ω    -39.00  23.00   0.50    0.15    --  -47.57  38.00 -30.00  124
 12  ω    -78.00 -36.00   0.50    0.15    --  -47.57 -38.00 -30.00   84
 13  ω    -27.00  24.00   0.50    0.15    --   47.57 -19.00 -90.00  102
 14  ω    -26.00  28.00   0.50    0.15    --   47.57 -19.00 -30.00  108
 15  ω   -121.00 -87.00   0.50    0.30    --  -99.00 -47.00 -41.25   68
 16  ω   -101.00 -76.00   0.50    0.30    --  -99.00 -77.00  30.00   50
 17  ω   -168.00-108.00   0.50    0.30    --  -99.00 -77.00  30.00  120
 18  ω   -110.00 -82.00   0.50    0.30    --  -99.00 -62.00 -32.69   56
 19  ω   -113.00 -87.00   0.50    0.30    --  -99.00 -30.00   0.00   52
 20  ω   -102.00 -76.00   0.50    0.30    --  -99.00 -77.00 -30.00   52
 21  ω   -115.00 -85.00   0.50    0.30    --  -99.00 -56.00 -59.75   60
 22  ω   -110.00 -76.00   0.50    0.30    --  -99.00 -77.00   0.00   68
 23  ω   -111.00 -85.00   0.50    0.30    --  -99.00 -61.00 -64.27   52
 24  ω   -167.00-107.00   0.50    0.30    --  -99.00 -77.00 -60.00  120
 25  ω   -107.00 -82.00   0.50    0.30    --  -99.00 -63.00 -54.42   50
 26  ω   -165.00-135.00   0.50    0.30    --  -99.00 -77.00   0.00   60
 27  ω   -164.00-117.00   0.50    0.30    --  -99.00 -61.00 -64.27   94
 28  ω   -133.00 -87.00   0.50    0.30    --  -99.00 -47.00 -58.58   92
 29  ω   -105.00 -77.00   0.50    0.30    --  -99.00 -75.00  14.05   56
 30  ω   -151.00-125.00   0.50    0.30    --  -99.00 -77.00 -94.05   52
 31  ω   -163.00-132.00   0.50    0.30    --  -99.00 -75.00  14.05   62
 32  ω   -102.00 -76.00   0.50    0.30    --  -99.00 -77.00 -60.00   52
 33  ω   -155.00-129.00   0.50    0.30    --  -99.00 -77.00 -30.00   52
 34  ω   -116.00 -83.00   0.50    0.30    --  -99.00 -61.00 -90.00   66
 35  ω    -69.00 -26.00   0.50    0.30    --  -99.00 125.00 -30.00   86
 36  ω   -111.00 -86.00   0.50    0.30    --  -99.00 -55.00  16.47   50
 37  ω   -115.00 -80.00   0.50    0.30    --  -99.00 -71.00 -81.03   70
 38  ω   -103.00 -78.00   0.50    0.30    --  -99.00 -77.00 -94.05   50
 39  ω   -112.00 -82.00   0.50    0.30    --  -99.00 -63.00 -66.96   60
 40  ω   -101.00 -75.00   0.50    0.30    --  -99.00 -79.00 -81.89   52
 41  ω   -167.00-142.00   0.50    0.30    --  -99.00 -63.00 -54.42   50
 42  ω     76.00 111.00   0.50    0.30    --  103.25-125.00  30.00   70
 43  ω     39.00  71.00   0.50    0.30    --  103.25-125.00  30.00   64
 44  ω     47.00  73.00   0.50    0.30    --  103.25 -61.00 -60.00   52
 45  ω     31.00  74.00   0.50    0.30    --  103.25 -61.00  90.00   86
 46  ω     82.00 111.00   0.50    0.30    --  103.25  77.00-120.00   58
 47  ω     68.00 104.00   0.50    0.30    --  103.25 -94.00  30.00   72
 48  ω     32.00  58.00   0.50    0.30    --  103.25 -94.00  30.00   52
 49  ω     32.00  70.00   0.50    0.30    --  103.25 -61.00-120.00   76
 50  ω     31.00  75.00   0.50    0.30    --  103.25 -61.00-150.00   88
 51  ω     34.00  74.00   0.50    0.30    --  103.25 -61.00 -90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1746422000
_diffrn_orient_matrix_UB_12      -0.0368966000
_diffrn_orient_matrix_UB_13      -0.0298302000
_diffrn_orient_matrix_UB_21      0.0232915000
_diffrn_orient_matrix_UB_22      0.0409705000
_diffrn_orient_matrix_UB_23      -0.1112344000
_diffrn_orient_matrix_UB_31      0.0288927000
_diffrn_orient_matrix_UB_32      -0.2551618000
_diffrn_orient_matrix_UB_33      -0.0135740000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8108
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.087
_diffrn_reflns_theta_min         5.127
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0673P)²+0.1947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1195
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1277
_reflns_number_total             1353
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0411_suppl.cif
_cod_data_source_block           tx9545
_cod_database_code               8104983
_chemical_oxdiff_formula         CHNOFe
_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.
;
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C3(H3), C5(H5), C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
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
O1 O 0.30212(10) 0.90728(14) 0.59710(6) 0.0360(3) Uani 1 1 d . . . . .
H1 H 0.353891 0.839600 0.558820 0.054 Uiso 1 1 calc R U . . .
N1 N 0.45803(11) 0.56189(17) 0.53242(7) 0.0300(3) Uani 1 1 d . . . . .
C1 C 0.27845(13) 0.7713(2) 0.67565(8) 0.0279(3) Uani 1 1 d . . . . .
C2 C 0.34302(12) 0.55183(19) 0.68682(8) 0.0268(3) Uani 1 1 d . . . . .
C3 C 0.31559(13) 0.4268(2) 0.77212(9) 0.0297(3) Uani 1 1 d . . . . .
H3 H 0.358807 0.283174 0.781215 0.036 Uiso 1 1 calc R U . . .
C4 C 0.15906(13) 0.7263(2) 0.83028(9) 0.0316(3) Uani 1 1 d . . . . .
C5 C 0.18639(13) 0.8530(2) 0.74673(9) 0.0315(3) Uani 1 1 d . . . . .
H5 H 0.142139 0.996017 0.737928 0.038 Uiso 1 1 calc R U . . .
C6 C 0.05916(15) 0.8211(3) 0.90552(10) 0.0416(4) Uani 1 1 d . . . . .
H6A H 0.122887 0.901629 0.956921 0.062 Uiso 1 1 calc R U . . .
H6B H 0.006817 0.699536 0.935541 0.062 Uiso 1 1 calc R U . . .
H6C H -0.015986 0.922749 0.872127 0.062 Uiso 1 1 calc R U . . .
C7 C 0.43169(13) 0.4520(2) 0.61207(9) 0.0278(3) Uani 1 1 d . . . . .
H7 H 0.470294 0.305800 0.621841 0.033 Uiso 1 1 calc R U . . .
C8 C 0.22629(14) 0.5107(2) 0.84307(9) 0.0323(3) Uani 1 1 d . . . . .
H8 H 0.210639 0.424396 0.899337 0.039 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 . .
C7 N1 N1 113.56(12) . 3_666
O1 C1 C2 122.27(10) . .
O1 C1 C5 118.00(10) . .
C5 C1 C2 119.73(11) . .
C1 C2 C7 122.26(10) . .
C3 C2 C1 117.99(10) . .
C3 C2 C7 119.73(10) . .
C2 C3 H3 119.1 . .
C8 C3 C2 121.85(11) . .
C8 C3 H3 119.1 . .
C5 C4 C6 119.91(12) . .
C5 C4 C8 118.89(10) . .
C8 C4 C6 121.21(12) . .
C1 C5 H5 119.2 . .
C4 C5 C1 121.58(11) . .
C4 C5 H5 119.2 . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
N1 C7 C2 121.26(11) . .
N1 C7 H7 119.4 . .
C2 C7 H7 119.4 . .
C3 C8 C4 119.92(11) . .
C3 C8 H8 120.0 . .
C4 C8 H8 120.0 . .
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 1.3544(14) .
N1 N1 1.3965(18) 3_666
N1 C7 1.2876(16) .
C1 C2 1.4132(17) .
C1 C5 1.3910(16) .
C2 C3 1.3994(16) .
C2 C7 1.4497(15) .
C3 H3 0.9300 .
C3 C8 1.3791(16) .
C4 C5 1.3850(17) .
C4 C6 1.5041(16) .
C4 C8 1.4032(18) .
C5 H5 0.9300 .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 H7 0.9300 .
C8 H8 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.82 1.92 2.6431(12) 146.1 . yes
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
O1 C1 C2 C3 178.17(10) . . . .
O1 C1 C2 C7 -3.60(17) . . . .
O1 C1 C5 C4 -178.71(10) . . . .
N1 N1 C7 C2 -178.55(10) 3_666 . . .
C1 C2 C3 C8 1.14(18) . . . .
C1 C2 C7 N1 1.30(18) . . . .
C2 C1 C5 C4 1.64(18) . . . .
C2 C3 C8 C4 0.51(19) . . . .
C3 C2 C7 N1 179.50(10) . . . .
C5 C1 C2 C3 -2.19(17) . . . .
C5 C1 C2 C7 176.03(10) . . . .
C5 C4 C8 C3 -1.12(18) . . . .
C6 C4 C5 C1 179.83(10) . . . .
C6 C4 C8 C3 179.09(11) . . . .
C7 C2 C3 C8 -177.13(10) . . . .
C8 C4 C5 C1 0.04(18) . . . .
