#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/02/2220238.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220238
loop_
_publ_author_name
'Han, Guo-zhi'
'Han, Lu-na'
'Lu, Ran-zhe'
'Zhang, Min'
'Wang, Hai-bo'
_publ_section_title
;
 2-Methyl-3-nitrobenzonitrile
;
_journal_coeditor_code           HK2576
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2468
_journal_paper_doi               10.1107/S1600536808039354
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C8 H6 N2 O2'
_chemical_formula_moiety         'C8 H6 N2 O2'
_chemical_formula_sum            'C8 H6 N2 O2'
_chemical_formula_weight         162.15
_chemical_name_systematic
;
2-Methyl-3-nitrobenzonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.80(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.025(3)
_cell_length_b                   7.3860(15)
_cell_length_c                   15.515(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1573.2(6)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0691
_diffrn_reflns_av_sigmaI/netI    0.0809
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2974
_diffrn_reflns_theta_full        25.28
_diffrn_reflns_theta_max         25.28
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.0762
_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/[σ²(Fo²)+(0.04P)²+1.75P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                1481
_reflns_number_total             2852
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2576.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220238
_cod_database_fobs_code          2220238
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.8903(3) 0.3923(5) 0.9651(2) 0.1022(11) Uani d . 1
O O2 0.8075(3) 0.2944(5) 0.8476(2) 0.1053(12) Uani d . 1
O O3 -0.2355(3) -0.1305(6) 0.2733(2) 0.1165(13) Uani d . 1
O O4 -0.2358(2) 0.0205(5) 0.3874(2) 0.0933(10) Uani d . 1
N N1 0.9792(3) -0.4285(6) 0.7823(3) 0.0911(13) Uani d . 1
N N2 0.8813(3) 0.2924(5) 0.9055(2) 0.0679(9) Uani d . 1
N N3 0.1646(3) 0.3683(6) 0.4808(3) 0.0913(12) Uani d . 1
N N4 -0.1954(3) -0.0405(6) 0.3328(3) 0.0848(12) Uani d . 1
C C1 0.8268(3) -0.0774(7) 0.8368(3) 0.0923(16) Uani d . 1
H H1A 0.7835 0.0171 0.8470 0.139 Uiso calc R 1
H H1B 0.8181 -0.1816 0.8713 0.139 Uiso calc R 1
H H1C 0.8128 -0.1092 0.7755 0.139 Uiso calc R 1
C C2 0.9291(3) -0.0132(5) 0.8624(2) 0.0510(9) Uani d U 1
C C3 0.9574(2) 0.1578(5) 0.8973(2) 0.0485(9) Uani d U 1
C C4 1.0540(3) 0.2126(6) 0.9250(2) 0.0674(11) Uani d U 1
H H4A 1.0702 0.3263 0.9494 0.081 Uiso calc R 1
C C5 1.1250(3) 0.0870(7) 0.9140(3) 0.0735(12) Uani d U 1
H H5A 1.1903 0.1195 0.9309 0.088 Uiso calc R 1
C C6 1.1036(3) -0.0738(6) 0.8811(3) 0.0687(11) Uani d U 1
H H6A 1.1534 -0.1538 0.8760 0.082 Uiso calc R 1
C C7 1.0072(3) -0.1268(5) 0.8534(2) 0.0538(9) Uani d U 1
C C8 0.9868(3) -0.3022(6) 0.8160(3) 0.0743(13) Uani d . 1
C C9 -0.0871(3) 0.2856(5) 0.4071(3) 0.0707(11) Uani d . 1
H H9A -0.0390 0.3709 0.4351 0.106 Uiso calc R 1
H H9B -0.1311 0.2595 0.4455 0.106 Uiso calc R 1
H H9C -0.1228 0.3360 0.3531 0.106 Uiso calc R 1
C C10 -0.0378(3) 0.1138(5) 0.3880(2) 0.0472(8) Uani d U 1
C C11 -0.0849(3) -0.0391(6) 0.3503(2) 0.0573(10) Uani d U 1
C C12 -0.0389(3) -0.1889(6) 0.3260(2) 0.0669(11) Uani d U 1
H H12A -0.0752 -0.2850 0.2977 0.080 Uiso calc R 1
C C13 0.0618(3) -0.1963(6) 0.3435(3) 0.0733(12) Uani d U 1
H H13A 0.0943 -0.2984 0.3295 0.088 Uiso calc R 1
C C14 0.1137(3) -0.0442(5) 0.3834(2) 0.0609(10) Uani d U 1
H H14A 0.1814 -0.0446 0.3950 0.073 Uiso calc R 1
C C15 0.0650(3) 0.1033(5) 0.4049(2) 0.0509(9) Uani d U 1
C C16 0.1190(3) 0.2561(6) 0.4443(3) 0.0646(11) Uani d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 N2 O2 120.7(4)
O1 N2 C3 121.9(4)
O2 N2 C3 117.4(4)
O3 N4 O4 122.9(5)
O3 N4 C11 116.7(4)
O4 N4 C11 119.0(4)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C7 114.3(3)
C3 C2 C1 125.0(4)
C7 C2 C1 120.7(4)
C4 C3 C2 124.2(3)
C4 C3 N2 116.7(3)
C2 C3 N2 119.1(3)
C3 C4 C5 116.3(4)
C3 C4 H4A 121.9
C5 C4 H4A 121.9
C6 C5 C4 122.7(4)
C6 C5 H5A 118.7
C4 C5 H5A 118.7
C5 C6 C7 120.7(4)
C5 C6 H6A 119.7
C7 C6 H6A 119.7
C6 C7 C2 121.9(4)
C6 C7 C8 119.0(4)
C2 C7 C8 119.0(4)
N1 C8 C7 171.6(6)
C10 C9 H9A 109.5
C10 C9 H9B 109.5
H9A C9 H9B 109.5
C10 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C11 C10 C15 114.6(3)
C11 C10 C9 125.2(3)
C15 C10 C9 120.2(3)
C12 C11 C10 124.5(4)
C12 C11 N4 117.8(4)
C10 C11 N4 117.7(4)
C11 C12 C13 119.7(4)
C11 C12 H12A 120.1
C13 C12 H12A 120.1
C12 C13 C14 118.0(4)
C12 C13 H13A 121.0
C14 C13 H13A 121.0
C15 C14 C13 120.3(4)
C15 C14 H14A 119.9
C13 C14 H14A 119.9
C14 C15 C10 122.8(3)
C14 C15 C16 119.3(3)
C10 C15 C16 117.9(3)
N3 C16 C15 174.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.169(4)
O2 N2 1.224(4)
O3 N4 1.182(5)
O4 N4 1.200(5)
N1 C8 1.063(5)
N2 C3 1.483(4)
N3 C16 1.125(5)
N4 C11 1.518(5)
C1 C2 1.485(5)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.399(5)
C2 C7 1.410(5)
C3 C4 1.396(5)
C4 C5 1.396(6)
C4 H4A 0.9300
C5 C6 1.304(6)
C5 H5A 0.9300
C6 C7 1.388(5)
C6 H6A 0.9300
C7 C8 1.425(6)
C9 C10 1.504(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 C11 1.376(5)
C10 C15 1.414(5)
C11 C12 1.372(5)
C12 C13 1.384(5)
C12 H12A 0.9300
C13 C14 1.410(5)
C13 H13A 0.9300
C14 C15 1.363(5)
C14 H14A 0.9300
C15 C16 1.426(5)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C1 H1A O2 . 0.96 2.08 2.768(6) 128.00
C1 H1C O2 2_646 0.96 2.38 3.229(6) 147.00
C4 H4A O1 3_767 0.93 2.47 3.390(6) 171.00
C9 H9B O4 . 0.96 2.35 2.831(5) 110.00
C9 H9C O3 2_455 0.96 2.50 3.400(4) 156.00
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13969780
2 PubChem 139075660
