Crystal structure of (E)-1-(2-nitrophenyl)-N-(o-tolyl)methanimine, C14H12N2O2
Olagboye, Sulaiman A.; Yusuf, Tunde L.; Oladipo, Segun D.; Zamisa, Sizwe J.; Zeitschrift für Kristallographie - New Crystal Structures 235 (2020) 833–836; doi:10.1515/ncrs-2020-0034

data_8105301
_publ_section_title
;
 Crystal structure of (E)-1-(2-nitrophenyl)-N-(o-tolyl)methanimine,
 C14H12N2O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              833
_journal_page_last               836
_journal_paper_doi               10.1515/ncrs-2020-0034
_journal_volume                  235
_journal_year                    2020
_chemical_absolute_configuration .
_chemical_formula_moiety         'C14 H12 N2 O2'
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 94.7860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.38440(10)
_cell_length_b                   20.0465(3)
_cell_length_c                   14.0511(2)
_cell_measurement_reflns_used    7160
_cell_measurement_temperature    150.02
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      4.48
_cell_volume                     2353.44(6)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.02
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0129
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14543
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.037
_diffrn_reflns_theta_min         2.438
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0348 before and 0.0273 after correction. The Ratio of minimum to maximum transmission is 0.9241. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 3440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         9464
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0573P)^2^+0.3691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_full    0.893
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                8295
_reflns_number_total             9464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2020-0034_suppl.cif
_cod_data_source_block           NOTO
_cod_database_code               8105301
_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
2. Rigid bond restraints
 C1C, C2C
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C14B(H14B), C11B(H11B), C12B(H12B), C6B(H6B), C13B(H13B), C8B(H8B), C5B(H5B),
 C3B(H3B), C4B(H4B), C8A(H8A), C3A(H3A), C4A(H4A), C11A(H11A), C6A(H6A),
 C5A(H5A), C13A(H13A), C12A(H12A), C14A(H14A), C8C(H8C), C3C(H3C), C4C(H4C),
 C11C(H11C), C6C(H6C), C5C(H5C), C12C(H12C), C14C(H14C), C13C(H13C), C14D(H14D),
  C6D(H6D), C13D(H13D), C11D(H11D), C8D(H8D), C12D(H12D), C5D(H5D), C3D(H3D),
 C4D(H4D)
3.b Idealised Me refined as rotating group:
 C1B(H1BA,H1BB,H1BC), C1A(H1AA,H1AB,H1AC), C1C(H1CA,H1CB,H1CC), C1D(H1DA,H1DB,
 H1DC)
;