#------------------------------------------------------------------------------
#$Date: 2015-06-06 05:28:16 +0300 (Sat, 06 Jun 2015) $
#$Revision: 138432 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/08/2240801.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_2240801
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Azcárate, Alexis'
'Kennedy, Alan R.'
_publ_section_title
;
 Crystal structure of 2-methyl-3-nitrobenzoic anhydride
;
_journal_coeditor_code           LH5768
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o451
_journal_paper_doi               10.1107/S2056989015010531
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C16 H12 N2 O7'
_chemical_formula_moiety         'C16 H12 N2 O7'
_chemical_formula_sum            'C16 H12 N2 O7'
_chemical_formula_weight         344.28
_chemical_melting_point          428.0(10)
_chemical_name_common            '2-Methyl-3-nitrobenzoic anhydride'
_chemical_name_systematic        '2-Methyl-3-nitrobenzoic anhydride'
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.930(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6332(5)
_cell_length_b                   11.6961(4)
_cell_length_c                   12.7934(6)
_cell_measurement_reflns_used    5209
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.18
_cell_measurement_theta_min      5.87
_cell_volume                     1475.95(13)
_computing_cell_refinement
;
CrysAlisPro (Oxford Diffraction, 2010)
;
_computing_data_collection
;
CrysAlisPro (Oxford Diffraction, 2010)
;
_computing_data_reduction
;
CrysAlisPro (Oxford Diffraction, 2010)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare et al., 1994)
;
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_sigmaI/netI    0.0600
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5209
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         73.181
_diffrn_reflns_theta_min         5.868
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.329
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0592
_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)+(0.0933P)²+1.5216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                1384
_reflns_number_total             1466
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5768sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1475.95(12)
_cod_database_code               2240801
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_occupancy
O O1 -0.22053(15) 0.30472(11) 0.21092(12) 0.0323(4) Uani d 1
O O2 -0.15352(15) 0.13946(12) 0.17543(12) 0.0348(4) Uani d 1
O O3 0.03327(14) 0.37124(12) 0.65687(11) 0.0303(4) Uani d 1
O O4 0.0000 0.21684(16) 0.7500 0.0270(5) Uani d 1
N N1 -0.17462(15) 0.20860(13) 0.23928(13) 0.0247(4) Uani d 1
C C1 -0.08126(16) 0.24457(15) 0.44518(15) 0.0214(4) Uani d 1
C C2 -0.14895(17) 0.17107(15) 0.35513(15) 0.0223(4) Uani d 1
C C3 -0.19730(18) 0.06382(15) 0.36540(16) 0.0254(4) Uani d 1
H H3 -0.2393 0.0172 0.3009 0.031 Uiso calc 1
C C4 -0.18356(18) 0.02561(16) 0.47094(16) 0.0275(4) Uani d 1
H H4 -0.2150 -0.0482 0.4804 0.033 Uiso calc 1
C C5 -0.12307(18) 0.09647(16) 0.56351(15) 0.0252(4) Uani d 1
H H5 -0.1164 0.0716 0.6361 0.030 Uiso calc 1
C C6 -0.07208(17) 0.20339(14) 0.55154(15) 0.0219(4) Uani d 1
C C7 -0.0176(2) 0.35437(16) 0.42891(16) 0.0284(5) Uani d 1
H H7A -0.0092 0.3536 0.3552 0.043 Uiso calc 1
H H7B 0.0724 0.3623 0.4883 0.043 Uiso calc 1
H H7C -0.0747 0.4189 0.4326 0.043 Uiso calc 1
C C8 -0.00896(18) 0.27684(16) 0.65334(15) 0.0231(4) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C8 O4 C8 2_556 119.5(2)
O1 N1 O2 . 123.96(16)
O1 N1 C2 . 118.41(15)
O2 N1 C2 . 117.56(15)
C2 C1 C6 . 114.35(16)
C2 C1 C7 . 122.01(16)
C6 C1 C7 . 123.55(15)
C3 C2 C1 . 125.05(17)
C3 C2 N1 . 115.58(15)
C1 C2 N1 . 119.37(15)
C4 C3 C2 . 118.77(16)
C4 C3 H3 . 120.6
C2 C3 H3 . 120.6
C3 C4 C5 . 119.17(17)
C3 C4 H4 . 120.4
C5 C4 H4 . 120.4
C4 C5 C6 . 121.08(17)
C4 C5 H5 . 119.5
C6 C5 H5 . 119.5
C5 C6 C1 . 121.47(16)
C5 C6 C8 . 119.12(16)
C1 C6 C8 . 119.39(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
O3 C8 O4 . 122.37(16)
O3 C8 C6 . 127.50(16)
O4 C8 C6 . 110.09(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 N1 . 1.225(2)
O2 N1 . 1.228(2)
O3 C8 . 1.186(2)
O4 C8 . 1.3939(19)
O4 C8 2_556 1.3939(19)
N1 C2 . 1.470(2)
C1 C2 . 1.402(2)
C1 C6 . 1.412(3)
C1 C7 . 1.502(2)
C2 C3 . 1.380(2)
C3 C4 . 1.377(3)
C3 H3 . 0.9500
C4 C5 . 1.391(3)
C4 H4 . 0.9500
C5 C6 . 1.394(2)
C5 H5 . 0.9500
C6 C8 . 1.494(2)
C7 H7A . 0.9800
C7 H7B . 0.9800
C7 H7C . 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
C3 H3 O1 4_445 0.95 2.52 3.204(2) 129.2
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_site_symmetry_1
_geom_torsion
C6 C1 C2 C3 . -3.8(3)
C7 C1 C2 C3 . 172.93(16)
C6 C1 C2 N1 . 175.09(14)
C7 C1 C2 N1 . -8.2(2)
O1 N1 C2 C3 . 132.42(17)
O2 N1 C2 C3 . -44.8(2)
O1 N1 C2 C1 . -46.6(2)
O2 N1 C2 C1 . 136.26(17)
C1 C2 C3 C4 . 2.4(3)
N1 C2 C3 C4 . -176.46(16)
C2 C3 C4 C5 . 0.8(3)
C3 C4 C5 C6 . -2.3(3)
C4 C5 C6 C1 . 0.8(3)
C4 C5 C6 C8 . 179.52(16)
C2 C1 C6 C5 . 2.1(2)
C7 C1 C6 C5 . -174.58(16)
C2 C1 C6 C8 . -176.64(14)
C7 C1 C6 C8 . 6.7(3)
C8 O4 C8 O3 2_556 25.06(14)
C8 O4 C8 C6 2_556 -157.20(15)
C5 C6 C8 O3 . -176.29(18)
C1 C6 C8 O3 . 2.5(3)
C5 C6 C8 O4 . 6.1(2)
C1 C6 C8 O4 . -175.15(14)

_cod_database_fobs_code 2240801
