Crystal structure of 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
Liu, Yingfan; Wang, Mengfei; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 995–997; doi:10.1515/ncrs-2023-0316

data_8107621
_publ_section_title
;
 Crystal structure of
 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile, C12H14N2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              995
_journal_page_last               997
_journal_paper_doi               10.1515/ncrs-2023-0316
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C12 H14 N2'
_chemical_formula_sum            'C12 H14 N2'
_chemical_formula_weight         186.25
_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                 95.9100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.16290(10)
_cell_length_b                   8.25800(10)
_cell_length_c                   13.4328(2)
_cell_measurement_reflns_used    2766
_cell_measurement_temperature    293.88(10)
_cell_measurement_theta_max      71.5950
_cell_measurement_theta_min      5.1760
_cell_volume                     1121.36(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.88(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.976
_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    -57.00   -19.00  1.00     1.00    --    0.00  -57.00  -180.00   38 
  2  \w    -18.00     7.00  1.00     1.00    --    0.00   57.00   -30.00   25 
  3  \w     19.00    50.00  1.00     1.00    --    0.00   57.00   -30.00   31 
  4  \w   -122.00   -87.00  1.00     1.00    --  -55.52  -99.00   -60.00   35 
  5  \w   -128.00   -86.00  1.00     1.00    --  -55.52 -125.00  -150.00   42 
  6  \w   -100.00   -36.00  1.00     1.00    --  -55.52  -57.00   -90.00   64 
  7  \w   -125.00   -79.00  1.00     1.00    --  -55.52  -99.00    90.00   46 
  8  \w      8.00   109.00  1.00     1.00    --   55.52   19.00  -150.00  101 
  9  \w     60.00    91.00  1.00    10.00    --  111.05 -111.00  -120.00   31 
  10 \w     46.00    84.00  1.00    10.00    --  111.05  -38.00     0.00   38 
  11 \w    100.00   161.00  1.00    10.00    --  111.05  111.00    90.00   61 
  12 \w     87.00   129.00  1.00    10.00    --  111.05  -38.00     0.00   42 
  13 \w    152.00   178.00  1.00    10.00    --  111.05   38.00  -120.00   26 
  14 \w     89.00   172.00  1.00    10.00    --  111.05   50.00  -180.00   83 
  15 \w     44.00   107.00  1.00    10.00    --  111.05 -111.00    60.00   63 
  16 \w     62.00   116.00  1.00    10.00    --  111.05  -64.00    90.00   54 
  17 \w     45.00   123.00  1.00    10.00    --  111.05  -50.00  -180.00   78'
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1189820000
_diffrn_orient_matrix_UB_12      -0.0643967000
_diffrn_orient_matrix_UB_13      -0.0689826000
_diffrn_orient_matrix_UB_21      0.0493695000
_diffrn_orient_matrix_UB_22      0.0913607000
_diffrn_orient_matrix_UB_23      -0.0890642000
_diffrn_orient_matrix_UB_31      0.0814731000
_diffrn_orient_matrix_UB_32      -0.1492763000
_diffrn_orient_matrix_UB_33      -0.0246446000
_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  0.0076
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3671
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.568
_diffrn_reflns_theta_min         6.301
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.512
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.024
_refine_ls_extinction_coef       0.0177(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2139
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0380
_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/[\s^2^(Fo^2^)+(0.0591P)^2^+0.1187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1960
_reflns_number_total             2139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0316_suppl_001.cif
_cod_data_source_block           hyj
_cod_database_code               8107621
_chemical_oxdiff_formula         'C1 H1 N1 '
_shelx_estimated_absorpt_t_max   0.814
_shelx_estimated_absorpt_t_min   0.749
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              71334
_shelx_hkl_checksum              6487
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.170
_oxdiff_exptl_absorpt_empirical_full_min 0.849