Crystal structure of a new monoclinic polymorph of <i>N</i>-(4-methylphenyl)-3-nitropyridin-2-amine
Aznan, Aina Mardia Akhmad; Abdullah, Zanariah; Lee, Vannajan Sanghiran; Tiekink, Edward R. T.; Acta Crystallographica Section E 70 (2014) 58–61; doi:10.1107/S1600536814012227

data_2239782
_publ_section_title
;
 Crystal structure of a new monoclinic polymorph of
 <i>N</i>-(4-methylphenyl)-3-nitropyridin-2-amine
;
_journal_coeditor_code           HB0011
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              58
_journal_page_last               61
_journal_paper_doi               10.1107/S1600536814012227
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H11 N3 O2'
_chemical_formula_moiety         'C12 H11 N3 O2'
_chemical_formula_sum            'C12 H11 N3 O2'
_chemical_formula_weight         229.24
_chemical_name_systematic
;
<i>N</i>-(4-methylphenyl)-3-nitropyridin-2-amine
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.387(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.4079(6)
_cell_length_b                   13.1968(8)
_cell_length_c                   14.3681(7)
_cell_measurement_reflns_used    4609
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3710
_cell_measurement_theta_min      3.0923
_cell_volume                     2149.7(2)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), <i>QMol</i> (Gans & Shalloway,
2001)
and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24994
_diffrn_reflns_theta_full        74.96
_diffrn_reflns_theta_max         74.96
_diffrn_reflns_theta_min         3.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2013)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     629
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0775P)^2^+0.0456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1236
_reflns_number_gt                3633
_reflns_number_total             4623
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            hb0011sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2239782
_cod_database_fobs_code          2239782