Crystal structure of 2-((E)-(((E)-2-hydroxy-4-methylbenzylidene) hydrazineylidene)methyl)-4-methylphenol, C16H16N2O2
Jin, Ze-Sen; Liu, Xiao-jing; Liu, E.; Jian, Fang-fang; Liang, Tongling; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 141–142; doi:10.1515/ncrs-2021-0411

data_8104983
_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 f\"ur 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  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -114.00 -61.00   0.50    0.15    --  -47.57 -16.00  47.00  106
  2  \w    -21.00   4.00   0.50    0.15    --  -47.57  16.00-142.00   50
  3  \w     40.00  79.00   0.50    0.15    --   47.57  16.00-142.00   78
  4  \w     -8.00  18.00   0.50    0.15    --   47.57 -16.00  47.00   52
  5  \w   -142.00-116.00   0.50    0.30    --  -99.00 -16.00  47.00   52
  6  \w     96.00 167.00   0.50    0.30    --  103.25  16.00-142.00  142
  7  \w    -74.00 -33.00   0.50    0.15    --  -47.57 -57.00 -60.00   82
  8  \w    -62.00 -37.00   0.50    0.15    --  -47.57 -19.00 -60.00   50
  9  \w    -77.00 -30.00   0.50    0.15    --  -47.57 -77.00 -90.00   94
 10  \w    -63.00 -25.00   0.50    0.15    --  -47.57 -77.00 -30.00   76
 11  \w    -39.00  23.00   0.50    0.15    --  -47.57  38.00 -30.00  124
 12  \w    -78.00 -36.00   0.50    0.15    --  -47.57 -38.00 -30.00   84
 13  \w    -27.00  24.00   0.50    0.15    --   47.57 -19.00 -90.00  102
 14  \w    -26.00  28.00   0.50    0.15    --   47.57 -19.00 -30.00  108
 15  \w   -121.00 -87.00   0.50    0.30    --  -99.00 -47.00 -41.25   68
 16  \w   -101.00 -76.00   0.50    0.30    --  -99.00 -77.00  30.00   50
 17  \w   -168.00-108.00   0.50    0.30    --  -99.00 -77.00  30.00  120
 18  \w   -110.00 -82.00   0.50    0.30    --  -99.00 -62.00 -32.69   56
 19  \w   -113.00 -87.00   0.50    0.30    --  -99.00 -30.00   0.00   52
 20  \w   -102.00 -76.00   0.50    0.30    --  -99.00 -77.00 -30.00   52
 21  \w   -115.00 -85.00   0.50    0.30    --  -99.00 -56.00 -59.75   60
 22  \w   -110.00 -76.00   0.50    0.30    --  -99.00 -77.00   0.00   68
 23  \w   -111.00 -85.00   0.50    0.30    --  -99.00 -61.00 -64.27   52
 24  \w   -167.00-107.00   0.50    0.30    --  -99.00 -77.00 -60.00  120
 25  \w   -107.00 -82.00   0.50    0.30    --  -99.00 -63.00 -54.42   50
 26  \w   -165.00-135.00   0.50    0.30    --  -99.00 -77.00   0.00   60
 27  \w   -164.00-117.00   0.50    0.30    --  -99.00 -61.00 -64.27   94
 28  \w   -133.00 -87.00   0.50    0.30    --  -99.00 -47.00 -58.58   92
 29  \w   -105.00 -77.00   0.50    0.30    --  -99.00 -75.00  14.05   56
 30  \w   -151.00-125.00   0.50    0.30    --  -99.00 -77.00 -94.05   52
 31  \w   -163.00-132.00   0.50    0.30    --  -99.00 -75.00  14.05   62
 32  \w   -102.00 -76.00   0.50    0.30    --  -99.00 -77.00 -60.00   52
 33  \w   -155.00-129.00   0.50    0.30    --  -99.00 -77.00 -30.00   52
 34  \w   -116.00 -83.00   0.50    0.30    --  -99.00 -61.00 -90.00   66
 35  \w    -69.00 -26.00   0.50    0.30    --  -99.00 125.00 -30.00   86
 36  \w   -111.00 -86.00   0.50    0.30    --  -99.00 -55.00  16.47   50
 37  \w   -115.00 -80.00   0.50    0.30    --  -99.00 -71.00 -81.03   70
 38  \w   -103.00 -78.00   0.50    0.30    --  -99.00 -77.00 -94.05   50
 39  \w   -112.00 -82.00   0.50    0.30    --  -99.00 -63.00 -66.96   60
 40  \w   -101.00 -75.00   0.50    0.30    --  -99.00 -79.00 -81.89   52
 41  \w   -167.00-142.00   0.50    0.30    --  -99.00 -63.00 -54.42   50
 42  \w     76.00 111.00   0.50    0.30    --  103.25-125.00  30.00   70
 43  \w     39.00  71.00   0.50    0.30    --  103.25-125.00  30.00   64
 44  \w     47.00  73.00   0.50    0.30    --  103.25 -61.00 -60.00   52
 45  \w     31.00  74.00   0.50    0.30    --  103.25 -61.00  90.00   86
 46  \w     82.00 111.00   0.50    0.30    --  103.25  77.00-120.00   58
 47  \w     68.00 104.00   0.50    0.30    --  103.25 -94.00  30.00   72
 48  \w     32.00  58.00   0.50    0.30    --  103.25 -94.00  30.00   52
 49  \w     32.00  70.00   0.50    0.30    --  103.25 -61.00-120.00   76
 50  \w     31.00  75.00   0.50    0.30    --  103.25 -61.00-150.00   88
 51  \w     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       '\w 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/[\s^2^(Fo^2^)+(0.0673P)^2^+0.1947P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_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)
;