#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:00:13 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301809 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/18/2311807.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_2311807
loop_
_publ_author_name
'Sparkes, Hazel A.'
'Sage, Henry J.'
'Yufit, Dmitry S.'
_publ_section_title
;
 In-situ cryocrystallization of 1,2-dimethyl-3-nitrobenzene and
 2,4-dimethyl-1-nitrobenzene.
;
_journal_issue                   'Pt 9'
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_page_first              872
_journal_page_last               875
_journal_paper_doi               10.1107/S2053229614017896
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C8 H9 N O2'
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_name_systematic
;
1,2-Dimethyl-3-nitrobenzene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9338(5)
_cell_length_b                   14.022(3)
_cell_length_c                   14.126(3)
_cell_measurement_reflns_used    1048
_cell_measurement_temperature    277(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.89
_cell_volume                     779.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      277(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.905
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5395
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         2.046
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0347
_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/[σ²(Fo²)+(0.0618P)²+0.1023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                744
_reflns_number_total             865
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gz3272sup1.cif
_cod_data_source_block           12-dimethyl-3-nitrobenzene
_cod_database_code               2311807
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           .2013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_occupancy
O O1 0.2726(8) 0.74176(13) 0.72084(14) 0.0978(8) Uani d 1
O O2 0.5030(9) 0.63406(15) 0.80610(12) 0.1066(11) Uani d 1
N N1 0.4050(7) 0.66406(14) 0.73069(14) 0.0677(6) Uani d 1
C C1 0.4585(7) 0.60547(14) 0.64549(14) 0.0504(6) Uani d 1
C C2 0.3744(7) 0.50913(13) 0.64624(14) 0.0485(6) Uani d 1
C C3 0.4354(8) 0.45899(14) 0.56239(15) 0.0532(6) Uani d 1
C C4 0.5762(8) 0.50585(17) 0.48559(15) 0.0646(7) Uani d 1
H H4 0.6218 0.4707 0.4295 0.077 Uiso calc 1
C C5 0.6519(9) 0.60098(19) 0.48771(17) 0.0684(8) Uani d 1
H H5 0.7465 0.6311 0.4335 0.082 Uiso calc 1
C C6 0.5912(8) 0.65258(16) 0.56797(16) 0.0611(7) Uani d 1
H H6 0.6388 0.7190 0.5704 0.073 Uiso calc 1
C C7 0.2173(8) 0.46018(18) 0.73060(17) 0.0671(7) Uani d 1
H H7A 0.3963 0.4301 0.7685 0.101 Uiso calc 1
H H7B 0.0572 0.4113 0.7088 0.101 Uiso calc 1
H H7C 0.0963 0.5072 0.7693 0.101 Uiso calc 1
C C8 0.3480(10) 0.35461(16) 0.5539(2) 0.0794(9) Uani d 1
H H8A 0.4189 0.3311 0.4916 0.119 Uiso calc 1
H H8B 0.1021 0.3462 0.5611 0.119 Uiso calc 1
H H8C 0.4665 0.3187 0.6034 0.119 Uiso calc 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 N1 C1 117.9(2)
O2 N1 O1 123.3(2)
O2 N1 C1 118.73(19)
C2 C1 N1 120.1(2)
C6 C1 N1 115.8(2)
C6 C1 C2 124.1(2)
C1 C2 C3 116.17(19)
C1 C2 C7 123.1(2)
C3 C2 C7 120.73(19)
C2 C3 C8 121.1(2)
C4 C3 C2 119.61(19)
C4 C3 C8 119.3(2)
C3 C4 H4 118.9
C5 C4 C3 122.2(2)
C5 C4 H4 118.9
C4 C5 H5 120.1
C6 C5 C4 119.8(2)
C6 C5 H5 120.1
C1 C6 H6 121.0
C5 C6 C1 118.1(2)
C5 C6 H6 121.0
C2 C7 H7A 109.5
C2 C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7B 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C3 C8 H8A 109.5
C3 C8 H8B 109.5
C3 C8 H8C 109.5
H8A C8 H8B 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.216(3)
O2 N1 1.208(3)
N1 C1 1.472(3)
C1 C2 1.391(3)
C1 C6 1.381(3)
C2 C3 1.398(3)
C2 C7 1.508(3)
C3 C4 1.384(3)
C3 C8 1.508(3)
C4 H4 0.9500
C4 C5 1.367(3)
C5 H5 0.9500
C5 C6 1.366(3)
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
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
C4 H4 O2 2_664 0.95 2.72 3.608(3) 156.7
C5 H5 O1 3_566 0.95 2.82 3.710(3) 156.8
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 N1 C1 C2 -134.4(3)
O1 N1 C1 C6 45.2(4)
O2 N1 C1 C2 47.7(4)
O2 N1 C1 C6 -132.7(3)
N1 C1 C2 C3 -179.7(2)
N1 C1 C2 C7 1.9(4)
N1 C1 C6 C5 178.7(2)
C1 C2 C3 C4 0.9(4)
C1 C2 C3 C8 -178.7(3)
C2 C1 C6 C5 -1.8(4)
C2 C3 C4 C5 -1.6(4)
C3 C4 C5 C6 0.6(5)
C4 C5 C6 C1 1.0(4)
C6 C1 C2 C3 0.8(4)
C6 C1 C2 C7 -177.6(3)
C7 C2 C3 C4 179.2(3)
C7 C2 C3 C8 -0.4(4)
C8 C3 C4 C5 178.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6739
