Crystal structure, DFT calculations and Hirshfeld surface analysis of 3-(4-methylphenyl)-6-nitro-1<i>H</i>-indazole
Ben-Yahia, Ali; El Bakri, Youness; Lai, Chin-Hung; Essassi, El Mokhtar; Mague, Joel T.; Acta Crystallographica Section E 74 (2018) 1857–1861; doi:10.1107/S205698901801647X

data_2242749
_publ_section_title
;
 Crystal structure, DFT calculations and Hirshfeld surface analysis of
 3-(4-methylphenyl)-6-nitro-1<i>H</i>-indazole
;
_journal_coeditor_code           FF2156
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1857
_journal_page_last               1861
_journal_paper_doi               10.1107/S205698901801647X
_journal_volume                  74
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C14 H11 N3 O3'
_chemical_formula_moiety         'C14 H11 N3 O3'
_chemical_formula_sum            'C14 H11 N3 O3'
_chemical_formula_weight         269.26
_chemical_name_systematic
;
3-(4-Methylphenyl)-6-nitro-1<i>H</i>-indazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.681(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1447(14)
_cell_length_b                   11.8380(12)
_cell_length_c                   7.4252(8)
_cell_measurement_reflns_used    1994
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.8
_cell_measurement_theta_min      3.37
_cell_volume                     1234.9(2)
_computing_cell_refinement
;
<i>SAINT</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>SAINT</i>  (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>DIAMOND</i> (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
<i>SHELXTL</i> (Sheldrick, 2008)
;
_computing_structure_refinement
;
<i>SHELXL2018</i> (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       \w-\f
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1105
_diffrn_reflns_av_unetI/netI     0.1621
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            25051
_diffrn_reflns_theta_full        30.500
_diffrn_reflns_theta_max         30.534
_diffrn_reflns_theta_min         1.720
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.317
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 891 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6667
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.1992
_refine_ls_R_factor_gt           0.0639
_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^)+(0.0622P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1584
_reflns_number_gt                2803
_reflns_number_total             6667
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ff2156sup1.cif
_cod_data_source_block           I
_cod_database_code               2242749
_cod_database_fobs_code          2242749
_shelx_hkl_checksum              11280
_shelx_res_checksum              55065