#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:01:59 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/52/2105260.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_2105260
loop_
_publ_author_name
'Britton, Doyle'
'Young, Jr, Victor G.'
'Noland, Wayland E.'
'Pinnow, Matthew J.'
'Clark, Christopher M.'
_publ_section_title
;
 Four polymorphs (polytypes) of 5,6-dimethylbenzofurazan 1-oxide
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              536
_journal_page_last               542
_journal_paper_doi               10.1107/S0108768112037457
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C10 H8 O3'
_chemical_formula_sum            'C10 H8 O3'
_chemical_formula_weight         176.16
_chemical_name_systematic
;
 4,5-dimethylphthalic anhydride
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.744(4)
_cell_length_b                   7.601(3)
_cell_length_c                   18.102(6)
_cell_measurement_reflns_used    3420
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     1615.9(10)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART 1K CCD area-detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0127
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17411
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        'less than 1'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS; Sheldrick, 2008; Blessing, 1995
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          .50
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .25
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.140
_refine_ls_extinction_coef       0.084(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.4380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                1772
_reflns_number_total             1857
_reflns_threshold_expression     '>2σ(I) '
_cod_data_source_file            ps5015.cif
_cod_data_source_block           Me2PA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               2105260
_cod_database_fobs_code          2105260
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
_atom_site_symmetry_multiplicity
C C1 0.05887(8) 0.21317(12) 0.48258(5) 0.0228(2) Uani d . 1 1
C C2 0.15461(8) 0.10774(13) 0.48559(5) 0.0232(2) Uani d . 1 1
C C3 0.20234(8) 0.05807(14) 0.55217(5) 0.0256(2) Uani d . 1 1
H H3 0.2689 -0.0129 0.5535 0.031 Uiso calc R 1 1
C C4 0.15040(8) 0.11466(13) 0.61746(5) 0.0248(2) Uani d . 1 1
C C5 0.05135(9) 0.22036(13) 0.61446(5) 0.0247(2) Uani d . 1 1
C C6 0.00614(8) 0.27159(13) 0.54630(5) 0.0248(2) Uani d . 1 1
H H6 -0.0593 0.3448 0.5439 0.030 Uiso calc R 1 1
C C7 0.02919(8) 0.23818(13) 0.40411(5) 0.0252(2) Uani d . 1 1
C C8 0.18618(9) 0.06185(13) 0.40921(5) 0.0261(2) Uani d . 1 1
C C9 0.19891(9) 0.05791(16) 0.69046(6) 0.0330(3) Uani d . 1 1
H H9A 0.1485 -0.0296 0.7131 0.049 Uiso calc R 1 1
H H9B 0.2054 0.1602 0.7232 0.049 Uiso calc R 1 1
H H9C 0.2744 0.0062 0.6828 0.049 Uiso calc R 1 1
C C10 -0.00697(10) 0.27670(16) 0.68445(6) 0.0328(3) Uani d . 1 1
H H10A -0.0751 0.3452 0.6722 0.049 Uiso calc R 1 1
H H10B 0.0451 0.3492 0.7138 0.049 Uiso calc R 1 1
H H10C -0.0290 0.1725 0.7129 0.049 Uiso calc R 1 1
O O11 -0.04487(7) 0.31905(11) 0.37500(4) 0.0350(2) Uani d . 1 1
O O12 0.26160(7) -0.02644(12) 0.38547(4) 0.0376(2) Uani d . 1 1
O O13 0.10748(6) 0.14088(9) 0.36216(4) 0.0276(2) Uani d . 1 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'
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 121.19(9)
C2 C1 C7 107.76(8)
C6 C1 C7 131.02(9)
C3 C2 C1 121.53(9)
C3 C2 C8 130.68(9)
C1 C2 C8 107.76(8)
C2 C3 C4 118.45(10)
C2 C3 H3 120.8
C4 C3 H3 120.8
C3 C4 C5 120.06(9)
C3 C4 C9 119.33(10)
C5 C4 C9 120.58(9)
C6 C5 C4 120.29(9)
C6 C5 C10 119.44(9)
C4 C5 C10 120.28(9)
C1 C6 C5 118.46(9)
C1 C6 H6 120.8
C5 C6 H6 120.8
O11 C7 O13 120.82(9)
O11 C7 C1 131.82(9)
O13 C7 C1 107.36(8)
O12 C8 O13 121.05(9)
O12 C8 C2 131.21(10)
O13 C8 C2 107.74(8)
C4 C9 H9A 109.5
C4 C9 H9B 109.5
H9A C9 H9B 109.5
C4 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C5 C10 H10A 109.5
C5 C10 H10B 109.5
H10A C10 H10B 109.5
C5 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C8 O13 C7 109.34(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3819(14)
C1 C6 1.3825(13)
C1 C7 1.4748(14)
C2 C3 1.3818(14)
C2 C8 1.4734(14)
C3 C4 1.3980(14)
C3 H3 0.9500
C4 C5 1.4147(15)
C4 C9 1.5023(13)
C5 C6 1.3984(14)
C5 C10 1.5027(14)
C6 H6 0.9500
C7 O11 1.1883(13)
C7 O13 1.4032(12)
C8 O12 1.1915(13)
C8 O13 1.3929(13)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
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 -0.76(15)
C7 C1 C2 C3 -178.93(9)
C6 C1 C2 C8 177.29(9)
C7 C1 C2 C8 -0.88(11)
C1 C2 C3 C4 1.03(15)
C8 C2 C3 C4 -176.52(9)
C2 C3 C4 C5 -0.04(15)
C2 C3 C4 C9 178.26(9)
C3 C4 C5 C6 -1.23(15)
C9 C4 C5 C6 -179.51(9)
C3 C4 C5 C10 178.03(9)
C9 C4 C5 C10 -0.25(15)
C2 C1 C6 C5 -0.52(15)
C7 C1 C6 C5 177.16(9)
C4 C5 C6 C1 1.50(15)
C10 C5 C6 C1 -177.77(9)
C2 C1 C7 O11 -179.21(11)
C6 C1 C7 O11 2.87(19)
C2 C1 C7 O13 1.77(10)
C6 C1 C7 O13 -176.15(10)
C3 C2 C8 O12 -1.61(19)
C1 C2 C8 O12 -179.42(11)
C3 C2 C8 O13 177.49(10)
C1 C2 C8 O13 -0.33(11)
O12 C8 O13 C7 -179.33(10)
C2 C8 O13 C7 1.46(10)
O11 C7 O13 C8 178.86(10)
C1 C7 O13 C8 -1.99(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 197112
2 PubChem 226644
