#------------------------------------------------------------------------------
#$Date: 2022-03-15 12:19:33 +0200 (Tue, 15 Mar 2022) $
#$Revision: 273694 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104757.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_8104757
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of 3,4-dichlorobenzoic acid chloride, C7H3Cl3O
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              531
_journal_page_last               532
_journal_paper_doi               10.1515/ncrs-2020-0561
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C7 H3 Cl3 O'
_chemical_formula_sum            'C7 H3 Cl3 O'
_chemical_formula_weight         209.44
_chemical_name_common            '3,4-dichlorobenzoic acid chloride'
_chemical_name_systematic        '3,4-dichlorobenzoic acid chloride'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 99.047(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0518(15)
_cell_length_b                   9.7403(11)
_cell_length_c                   6.9562(9)
_cell_measurement_reflns_used    3160
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.70
_cell_volume                     806.42(17)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.798
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.798
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2002
_diffrn_reflns_point_group_measured_fraction_full 0.798
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_min         1.711
_exptl_absorpt_coefficient_mu    1.066
_exptl_absorpt_correction_T_max  0.745686
_exptl_absorpt_correction_T_min  0.549503
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
twinabs 2008/2[6]                                         
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_description       rod
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         2002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0316
_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)+(0.0220P)²+0.4406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1808
_reflns_number_total             2002
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0561_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104757
_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.
;
_shelx_estimated_absorpt_t_min   0.593
_shelx_estimated_absorpt_t_max   0.899
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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.35680(6) 0.66021(8) 0.52956(16) 0.0565(3) Uani 1 1 d . . . . .
Cl2 Cl 0.40849(6) 0.11079(7) 0.56444(12) 0.0451(2) Uani 1 1 d . . . . .
Cl3 Cl 0.16817(6) -0.01885(6) 0.44037(10) 0.03717(16) Uani 1 1 d . . . . .
O1 O 0.14380(17) 0.66732(19) 0.4227(4) 0.0464(5) Uani 1 1 d . . . . .
C1 C 0.21339(18) 0.4394(2) 0.4596(4) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.30568(19) 0.3547(2) 0.5118(4) 0.0271(5) Uani 1 1 d . . . . .
H2 H 0.377974 0.393212 0.552342 0.033 Uiso 1 1 calc R U . . .
C3 C 0.29183(19) 0.2137(2) 0.5044(4) 0.0269(5) Uani 1 1 d . . . . .
C4 C 0.1860(2) 0.1570(2) 0.4483(4) 0.0267(5) Uani 1 1 d . . . . .
C5 C 0.09342(18) 0.2414(3) 0.3976(4) 0.0285(5) Uani 1 1 d . . . . .
H5 H 0.021008 0.202565 0.359513 0.034 Uiso 1 1 calc R U . . .
C6 C 0.10688(19) 0.3822(2) 0.4026(4) 0.0276(5) Uani 1 1 d . . . . .
H6 H 0.043666 0.440337 0.367211 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2206(2) 0.5910(2) 0.4619(4) 0.0308(5) 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'
O O 0.0106 0.0060 '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'
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 120.0(2) . .
C2 C1 C7 123.2(2) . .
C6 C1 C7 116.8(2) . .
C3 C2 C1 119.6(2) . .
C3 C2 H2 120.2 . .
C1 C2 H2 120.2 . .
C2 C3 C4 120.3(2) . .
C2 C3 Cl2 118.63(18) . .
C4 C3 Cl2 121.02(18) . .
C5 C4 C3 120.2(2) . .
C5 C4 Cl3 119.26(19) . .
C3 C4 Cl3 120.53(18) . .
C6 C5 C4 119.7(2) . .
C6 C5 H5 120.1 . .
C4 C5 H5 120.1 . .
C5 C6 C1 120.1(2) . .
C5 C6 H6 119.9 . .
C1 C6 H6 119.9 . .
O1 C7 C1 125.5(2) . .
O1 C7 Cl1 118.71(19) . .
C1 C7 Cl1 115.76(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C7 1.768(3) .
Cl2 C3 1.724(2) .
Cl3 C4 1.727(2) .
O1 C7 1.186(3) .
C1 C2 1.387(3) .
C1 C6 1.398(3) .
C1 C7 1.479(3) .
C2 C3 1.383(3) .
C2 H2 0.9500 .
C3 C4 1.388(3) .
C4 C5 1.387(3) .
C5 C6 1.380(4) .
C5 H5 0.9500 .
C6 H6 0.9500 .
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
C5 H5 O1 0.95 2.59 3.414(3) 145.7 2_545
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
C6 C1 C2 C3 0.9(4) . . . .
C7 C1 C2 C3 -179.6(2) . . . .
C1 C2 C3 C4 -1.1(4) . . . .
C1 C2 C3 Cl2 178.5(2) . . . .
C2 C3 C4 C5 0.5(4) . . . .
Cl2 C3 C4 C5 -179.0(2) . . . .
C2 C3 C4 Cl3 -179.58(18) . . . .
Cl2 C3 C4 Cl3 0.9(3) . . . .
C3 C4 C5 C6 0.2(4) . . . .
Cl3 C4 C5 C6 -179.71(19) . . . .
C4 C5 C6 C1 -0.3(4) . . . .
C2 C1 C6 C5 -0.2(4) . . . .
C7 C1 C6 C5 -179.7(2) . . . .
C2 C1 C7 O1 -178.3(3) . . . .
C6 C1 C7 O1 1.3(4) . . . .
C2 C1 C7 Cl1 1.8(3) . . . .
C6 C1 C7 Cl1 -178.69(19) . . . .
