#------------------------------------------------------------------------------
#$Date: 2023-03-01 11:24:38 +0200 (Wed, 01 Mar 2023) $
#$Revision: 281206 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/67/8106792.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106792
loop_
_publ_author_name
'Qu, Hai-Tao'
'Fu, Ying'
'Ye, Fei'
_publ_section_title
;
 Crystal structure of 2,4-dichlorobenzene anhydride, C14H6Cl4O3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              85
_journal_page_last               86
_journal_paper_doi               10.1515/ncrs-2015-0036
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety
;
 'C14 H6 Cl4 O3'  
;
_chemical_formula_sum            'C14 H6 Cl4 O3'
_chemical_formula_weight         363.99
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.884(2)
_cell_length_b                   11.902(2)
_cell_length_c                   10.509(2)
_cell_measurement_reflns_used    8707
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     1486.4(5)
_computing_cell_refinement       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_collection       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10417
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.10
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  0.8833
_exptl_absorpt_correction_T_min  0.8361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
ABSCOR (Higashi, 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0440
_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)+(0.0463P)²+0.7257P] where P=(Fo²+2Fc²)/3'
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1033
_reflns_number_total             1303
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0036_Suppl.cif
_cod_data_source_block           1
_cod_database_code               8106792
_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.
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.09041(8) 0.25896(6) 1.07622(10) 0.0800(4) Uani 1 1 d . . .
Cl2 Cl -0.00610(8) 0.51465(8) 0.67797(8) 0.0770(3) Uani 1 1 d . . .
O1 O 0.14234(18) 0.70622(18) 0.67949(19) 0.0637(6) Uani 1 1 d . . .
C1 C 0.0757(2) 0.4965(2) 0.8124(2) 0.0480(7) Uani 1 1 d . . .
O2 O 0.2500 0.7500 0.8473(3) 0.0657(8) Uani 1 2 d S . .
C7 C 0.1789(2) 0.6794(2) 0.7799(3) 0.0468(6) Uani 1 1 d . . .
C2 C 0.0571(2) 0.3995(2) 0.8808(3) 0.0536(7) Uani 1 1 d . . .
H2 H 0.0039 0.3476 0.8534 0.064 Uiso 1 1 calc R . .
C5 C 0.2162(2) 0.5517(2) 0.9631(3) 0.0480(6) Uani 1 1 d . . .
H5 H 0.2700 0.6027 0.9912 0.058 Uiso 1 1 calc R . .
C6 C 0.1564(2) 0.57491(19) 0.8518(2) 0.0427(6) Uani 1 1 d . . .
C4 C 0.1976(2) 0.4555(2) 1.0325(3) 0.0549(7) Uani 1 1 d . . .
H4 H 0.2382 0.4415 1.1065 0.066 Uiso 1 1 calc R . .
C3 C 0.1180(2) 0.3801(2) 0.9903(3) 0.0523(7) Uani 1 1 d . . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 120.9(3) . .
C2 C1 Cl2 116.2(2) . .
C6 C1 Cl2 122.9(2) . .
C7 O2 C7 118.6(3) . 2_565
O1 C7 O2 121.0(2) . .
O1 C7 C6 128.0(3) . .
O2 C7 C6 111.0(2) . .
C1 C2 C3 119.4(2) . .
C1 C2 H2 120.3 . .
C3 C2 H2 120.3 . .
C4 C5 C6 121.8(3) . .
C4 C5 H5 119.1 . .
C6 C5 H5 119.1 . .
C5 C6 C1 117.6(2) . .
C5 C6 C7 120.2(2) . .
C1 C6 C7 122.2(2) . .
C5 C4 C3 118.8(3) . .
C5 C4 H4 120.6 . .
C3 C4 H4 120.6 . .
C4 C3 C2 121.4(2) . .
C4 C3 Cl1 120.3(2) . .
C2 C3 Cl1 118.4(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C3 1.732(3) .
Cl2 C1 1.728(3) .
O1 C7 1.185(3) .
C1 C2 1.378(4) .
C1 C6 1.401(4) .
O2 C7 1.386(3) .
O2 C7 1.386(3) 2_565
C7 C6 1.479(4) .
C2 C3 1.378(4) .
C2 H2 0.9300 .
C5 C4 1.375(4) .
C5 C6 1.396(4) .
C5 H5 0.9300 .
C4 C3 1.377(4) .
C4 H4 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O1 0.93 2.44 3.363(3) 170.1 3_546
C5 H5 O1 0.93 2.55 3.374(3) 147.3 8_656
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
Cl1 C3 C4 C5 -178.99(21) . . . .
Cl1 C3 C2 C1 178.53(20) . . . .
Cl2 C1 C2 C3 -179.00(20) . . . .
Cl2 C1 C6 C7 -0.768(330) . . . .
Cl2 C1 C6 C5 179.09(19) . . . .
O1 C7 O2 C7 -31.64(36) . . . .
C7 O2 C7 C6 149.87(21) . . . .
O1 C7 C6 C5 173.19(27) . . . .
O1 C7 C6 C1 -7.0(4) . . . .
