#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/17/2231776.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_2231776
loop_
_publ_author_name
'Johnston, Dean H.'
'Crather, Heather M.'
_publ_section_title
;
 2,5-Dimethyl-1,3-dinitrobenzene
;
_journal_coeditor_code           ZL2394
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2276
_journal_page_last               o2277
_journal_paper_doi               10.1107/S1600536811031424
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C8 H8 N2 O4'
_chemical_formula_moiety         'C8 H8 N2 O4'
_chemical_formula_sum            'C8 H8 N2 O4'
_chemical_formula_weight         196.16
_chemical_melting_point          398.40(10)
_chemical_name_common            2,6-dinitro-p-xylene
_chemical_name_systematic
;
2,5-Dimethyl-1,3-dinitrobenzene
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2011.4-1'
_cell_angle_alpha                90
_cell_angle_beta                 91.963(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.582(3)
_cell_length_b                   9.3868(17)
_cell_length_c                   7.3565(14)
_cell_measurement_reflns_used    2569
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      24.6966
_cell_measurement_theta_min      3.5161
_cell_volume                     868.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'GIS (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and
POV-Ray (Cason, 2004)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART X2S benchtop'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2868
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Bruker, 2009)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.153
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1540
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0385
_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)+(0.0667P)²+0.0091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                1307
_reflns_number_total             1540
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2394.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231776
_cod_database_fobs_code          2231776
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
C C1 0.26217(13) 0.14793(18) 0.1233(2) 0.0281(4) Uani d . 1.0
C C2 0.16617(13) 0.22131(17) 0.1367(2) 0.0295(4) Uani d . 1.0
C C3 0.15567(13) 0.36737(19) 0.1375(2) 0.0323(4) Uani d . 1.0
H H3 0.0873 0.409 0.1472 0.039 Uiso calc R 1.0
C C4 0.24416(13) 0.45384(18) 0.1243(2) 0.0304(4) Uani d . 1.0
C C5 0.34132(13) 0.38694(17) 0.1104(2) 0.0302(4) Uani d . 1.0
H H5 0.4038 0.4426 0.0995 0.036 Uiso calc R 1.0
C C6 0.34884(11) 0.2402(2) 0.1123(2) 0.0279(4) Uani d . 1.0
C C7 0.26878(16) -0.01147(18) 0.1075(2) 0.0402(5) Uani d . 1.0
H H7A 0.2846 -0.0527 0.2278 0.06 Uiso calc R 1.0
H H7B 0.3253 -0.0369 0.0251 0.06 Uiso calc R 1.0
H H7C 0.2007 -0.0488 0.0594 0.06 Uiso calc R 1.0
C C8 0.23407(16) 0.61384(19) 0.1237(3) 0.0438(5) Uani d . 1.0
H H8A 0.1999 0.6449 0.0087 0.066 Uiso calc PR 0.616(19)
H H8B 0.3049 0.6568 0.1369 0.066 Uiso calc PR 0.616(19)
H H8C 0.1908 0.6439 0.2252 0.066 Uiso calc PR 0.616(19)
H H8D 0.2639 0.6521 0.2385 0.066 Uiso calc PR 0.384(19)
H H8E 0.1589 0.6403 0.1103 0.066 Uiso calc PR 0.384(19)
H H8F 0.273 0.6532 0.022 0.066 Uiso calc PR 0.384(19)
N N1 0.06685(12) 0.14007(19) 0.1519(2) 0.0426(4) Uani d . 1.0
N N2 0.45679(12) 0.18168(17) 0.1043(2) 0.0400(4) Uani d . 1.0
O O1 0.06653(12) 0.03920(18) 0.25790(19) 0.0589(5) Uani d . 1.0
O O2 -0.00966(11) 0.17884(17) 0.0609(2) 0.0687(5) Uani d . 1.0
O O3 0.47671(12) 0.07044(16) 0.18286(19) 0.0563(4) Uani d . 1.0
O O4 0.52229(10) 0.2493(2) 0.0219(3) 0.0705(5) Uani d . 1.0
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
C2 C1 C6 112.13(15)
C2 C1 C7 123.13(15)
C6 C1 C7 124.56(15)
C3 C2 C1 125.06(15)
C3 C2 N1 115.70(15)
C1 C2 N1 119.24(15)
C2 C3 C4 120.39(15)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 117.05(15)
C5 C4 C8 121.84(15)
C3 C4 C8 121.11(15)
C6 C5 C4 120.89(15)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C1 124.46(15)
C5 C6 N2 115.87(15)
C1 C6 N2 119.67(15)
C1 C7 H7A 109.5
C1 C7 H7B 109.5
H7A C7 H7B 109.5
C1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C4 C8 H8A 109.5
C4 C8 H8B 109.5
H8A C8 H8B 109.5
C4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C4 C8 H8D 109.5
H8A C8 H8D 141.1
H8B C8 H8D 56.3
H8C C8 H8D 56.3
C4 C8 H8E 109.5
H8A C8 H8E 56.3
H8B C8 H8E 141.1
H8C C8 H8E 56.3
H8D C8 H8E 109.5
C4 C8 H8F 109.5
H8A C8 H8F 56.3
H8B C8 H8F 56.3
H8C C8 H8F 141.1
H8D C8 H8F 109.5
H8E C8 H8F 109.5
O2 N1 O1 124.35(16)
O2 N1 C2 117.61(17)
O1 N1 C2 118.03(15)
O3 N2 O4 123.52(15)
O3 N2 C6 118.60(16)
O4 N2 C6 117.87(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.397(2)
C1 C6 1.397(2)
C1 C7 1.503(2)
C2 C3 1.377(3)
C2 N1 1.471(2)
C3 C4 1.384(2)
C3 H3 0.95
C4 C5 1.381(2)
C4 C8 1.507(2)
C5 C6 1.380(2)
C5 H5 0.95
C6 N2 1.468(2)
C7 H7A 0.98
C7 H7B 0.98
C7 H7C 0.98
C8 H8A 0.98
C8 H8B 0.98
C8 H8C 0.98
C8 H8D 0.98
C8 H8E 0.98
C8 H8F 0.98
N1 O2 1.210(2)
N1 O1 1.227(2)
N2 O3 1.2154(19)
N2 O4 1.218(2)
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
C3 H3 O1 2 0.95 2.41 3.340(2) 165.4
C5 H5 O3 2_655 0.95 2.47 3.207(2) 134.4
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
C6 C1 C2 C3 0.6(2)
C7 C1 C2 C3 -174.82(17)
C6 C1 C2 N1 -179.20(14)
C7 C1 C2 N1 5.4(2)
C1 C2 C3 C4 0.1(3)
N1 C2 C3 C4 179.84(15)
C2 C3 C4 C5 0.0(2)
C2 C3 C4 C8 179.58(16)
C3 C4 C5 C6 -0.8(2)
C8 C4 C5 C6 179.64(16)
C4 C5 C6 C1 1.6(3)
C4 C5 C6 N2 -177.55(14)
C2 C1 C6 C5 -1.4(2)
C7 C1 C6 C5 173.92(17)
C2 C1 C6 N2 177.72(14)
C7 C1 C6 N2 -7.0(2)
C3 C2 N1 O2 44.2(2)
C1 C2 N1 O2 -136.03(18)
C3 C2 N1 O1 -134.69(17)
C1 C2 N1 O1 45.1(2)
C5 C6 N2 O3 147.42(16)
C1 C6 N2 O3 -31.8(2)
C5 C6 N2 O4 -31.1(2)
C1 C6 N2 O4 149.73(18)
