#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/27/2102736.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_2102736
loop_
_publ_author_name
'Bujak, Maciej'
'Dziubek, Kamil'
'Katrusiak, Andrzej'
_publ_section_title
;
 Halogen···halogen interactions in pressure-frozen
 ortho- and meta-dichlorobenzene isomers
;
_journal_coeditor_code           SO5006
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              124
_journal_page_last               131
_journal_paper_doi               10.1107/S0108768106046684
_journal_volume                  63
_journal_year                    2007
_chemical_formula_moiety         'C6 H4 Cl2'
_chemical_formula_sum            'C6 H4 Cl2'
_chemical_formula_weight         146.99
_chemical_melting_point          256.4
_chemical_name_common
;
 1,2-dichlorobenzene
 ortho-dichlorobenzene
;
_chemical_name_systematic
;
 1,2-dichlorobenzene
 ortho-dichlorobenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     Patterson
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.70(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9274(4)
_cell_length_b                   10.5678(10)
_cell_length_c                   15.199(9)
_cell_measurement_reflns_used    1765
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.34
_cell_volume                     626.5(4)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2004)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2004)'
_computing_data_reduction
'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A.  2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.390
_diffrn_measured_fraction_theta_max 0.390
_diffrn_measurement_device_type  'KM-4 CCD'
_diffrn_measurement_method       'φ- and 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  0.0693
_diffrn_reflns_av_sigmaI/netI    0.4872
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            3835
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         3.86
_exptl_absorpt_coefficient_mu    0.911
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
 Correction for absorption of the diamond-anvil cell and the sample
 were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
 Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
 219, 461-467).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.632
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         431
_refine_ls_number_restraints     111
_refine_ls_restrained_S_all      0.578
_refine_ls_R_factor_all          0.2098
_refine_ls_R_factor_gt           0.0309
_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)+(0.0138P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0325
_refine_ls_wR_factor_ref         0.0372
_reflns_number_gt                133
_reflns_number_total             431
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            so5006.cif
_cod_data_source_block           oDCB
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2102736
_cod_database_fobs_code          2102736
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
Cl Cl1 -0.0111(6) 0.80323(19) 0.7942(5) 0.100(4) Uani d U 1
Cl Cl2 -0.2769(4) 0.99043(12) 0.6415(3) 0.0646(19) Uani d U 1
C C1 0.0274(16) 0.7634(7) 0.6869(15) 0.051(4) Uani d DU 1
C C2 -0.103(3) 0.8469(7) 0.6220(11) 0.054(5) Uani d DU 1
C C3 -0.073(2) 0.8126(8) 0.5341(13) 0.060(5) Uani d DU 1
H H3 -0.1529 0.8670 0.4882 0.072 Uiso calc R 1
C C4 0.0759(13) 0.6978(6) 0.5150(10) 0.068(4) Uani d DU 1
H H4 0.0961 0.6751 0.4567 0.082 Uiso calc R 1
C C5 0.191(2) 0.6195(7) 0.5830(10) 0.065(5) Uani d DU 1
H H5 0.2894 0.5425 0.5705 0.078 Uiso calc R 1
C C6 0.166(2) 0.6512(6) 0.6701(11) 0.058(5) Uani d DU 1
H H6 0.2438 0.5963 0.7159 0.070 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.1007(15) 0.0817(13) 0.121(14) -0.0101(12) 0.024(3) -0.002(3)
Cl2 0.0658(7) 0.0566(8) 0.071(6) 0.0029(9) 0.0039(11) 0.004(2)
C1 0.044(3) 0.060(3) 0.047(13) -0.003(3) -0.002(8) -0.011(6)
C2 0.050(3) 0.051(3) 0.063(15) -0.003(3) 0.017(8) 0.005(6)
C3 0.052(4) 0.070(3) 0.054(13) -0.006(3) -0.009(9) 0.004(7)
C4 0.065(4) 0.082(3) 0.061(13) -0.014(3) 0.024(7) -0.016(6)
C5 0.056(4) 0.061(4) 0.079(14) 0.002(4) 0.018(8) -0.020(5)
C6 0.055(4) 0.051(3) 0.068(13) 0.000(3) 0.008(10) -0.002(5)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 C2 Cl2 124.7(13) y
C1 C2 C3 116.8(11) y
C1 C6 C5 118.2(14) y
C2 C1 Cl1 117.3(9) y
C3 C2 Cl2 118.4(9) y
C4 C3 C2 120.6(14) y
C4 C5 C6 121.8(9) y
C5 C4 C3 118.8(14) y
C6 C1 Cl1 118.9(14) y
C6 C1 C2 123.7(17) y
C1 C6 H6 120.9 ?
C2 C3 H3 119.7 ?
C3 C4 H4 120.6 ?
C4 C3 H3 119.7 ?
C4 C5 H5 119.1 ?
C5 C4 H4 120.6 ?
C5 C6 H6 120.9 ?
C6 C5 H5 119.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.71(2) y
C1 C2 1.376(18) y
C1 C6 1.342(10) y
Cl2 C2 1.704(9) y
C2 C3 1.403(19) y
C3 C4 1.391(11) y
C4 C5 1.359(16) y
C5 C6 1.379(17) y
C3 H3 0.9300 ?
C4 H4 0.9300 ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
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
C1 C2 C3 C4 1.3(17)
C2 C1 C6 C5 2.3(15)
C2 C3 C4 C5 0.1(16)
C3 C4 C5 C6 -0.4(17)
C4 C5 C6 C1 -0.8(18)
C6 C1 C2 C3 -2.6(14)
C6 C1 C2 Cl2 -179.4(7)
Cl1 C1 C2 C3 -179.4(10)
Cl1 C1 C6 C5 179.1(8)
Cl1 C1 C2 Cl2 3.9(10)
Cl2 C2 C3 C4 178.3(4)
loop_
_refln_index_h
_refln_index_k
_refln_index_l
2 0 0
1 1 0
2 1 0
3 1 0
4 1 0
0 2 0
1 2 0
2 2 0
3 2 0
4 2 0
1 3 0
2 3 0
3 3 0
4 3 0
0 4 0
1 4 0
2 4 0
3 4 0
4 4 0
1 5 0
2 5 0
3 5 0
4 5 0
0 6 0
1 6 0
2 6 0
3 6 0
4 6 0
1 7 0
2 7 0
3 7 0
0 8 0
1 8 0
2 8 0
1 9 0
3 9 0
0 10 0
1 10 0
1 11 0
2 11 0
0 12 0
1 12 0
-3 0 1
-1 0 1
1 0 1
3 0 1
-4 1 1
-3 1 1
-2 1 1
-1 1 1
1 1 1
2 1 1
3 1 1
4 1 1
-4 2 1
-3 2 1
-2 2 1
-1 2 1
0 2 1
1 2 1
2 2 1
3 2 1
4 2 1
-4 3 1
-3 3 1
-2 3 1
-1 3 1
0 3 1
1 3 1
2 3 1
3 3 1
-4 4 1
-3 4 1
-2 4 1
0 4 1
1 4 1
2 4 1
3 4 1
4 4 1
-4 5 1
-3 5 1
-2 5 1
-1 5 1
0 5 1
1 5 1
2 5 1
3 5 1
4 5 1
-4 6 1
-3 6 1
-2 6 1
-1 6 1
0 6 1
1 6 1
2 6 1
3 6 1
4 6 1
-3 7 1
-2 7 1
-1 7 1
0 7 1
1 7 1
2 7 1
-3 8 1
-2 8 1
-1 8 1
0 8 1
1 8 1
2 8 1
3 8 1
-3 9 1
-2 9 1
-1 9 1
0 9 1
1 9 1
2 9 1
3 9 1
-2 10 1
-1 10 1
0 10 1
1 10 1
2 10 1
-2 11 1
-1 11 1
0 11 1
1 11 1
2 11 1
-1 12 1
0 12 1
1 12 1
-4 0 2
-2 0 2
2 0 2
4 0 2
-3 1 2
-2 1 2
-1 1 2
1 1 2
3 1 2
4 1 2
-4 2 2
-3 2 2
-2 2 2
-1 2 2
1 2 2
2 2 2
3 2 2
4 2 2
-4 3 2
-3 3 2
-2 3 2
-1 3 2
0 3 2
1 3 2
2 3 2
3 3 2
4 3 2
-4 4 2
-2 4 2
-1 4 2
0 4 2
1 4 2
2 4 2
4 4 2
-4 5 2
-3 5 2
-2 5 2
-1 5 2
0 5 2
1 5 2
2 5 2
3 5 2
4 5 2
-4 6 2
-3 6 2
-2 6 2
-1 6 2
0 6 2
1 6 2
2 6 2
3 6 2
-3 7 2
-2 7 2
-1 7 2
0 7 2
1 7 2
2 7 2
-3 8 2
-2 8 2
-1 8 2
0 8 2
1 8 2
2 8 2
3 8 2
-3 9 2
-2 9 2
-1 9 2
0 9 2
1 9 2
2 9 2
3 9 2
-2 10 2
-1 10 2
0 10 2
1 10 2
2 10 2
-1 11 2
0 11 2
1 11 2
2 11 2
-1 12 2
0 12 2
1 12 2
-3 0 3
3 0 3
-4 1 3
-3 1 3
-2 1 3
2 1 3
3 1 3
4 1 3
-4 2 3
-3 2 3
-2 2 3
2 2 3
3 2 3
4 2 3
-4 3 3
-3 3 3
-2 3 3
-1 3 3
1 3 3
2 3 3
3 3 3
4 3 3
-4 4 3
-3 4 3
-2 4 3
-1 4 3
0 4 3
1 4 3
2 4 3
3 4 3
4 4 3
-4 5 3
-3 5 3
-2 5 3
-1 5 3
0 5 3
1 5 3
2 5 3
3 5 3
4 5 3
-4 6 3
-3 6 3
-2 6 3
-1 6 3
0 6 3
1 6 3
2 6 3
3 6 3
-3 7 3
-2 7 3
-1 7 3
0 7 3
1 7 3
2 7 3
3 7 3
-3 8 3
-2 8 3
-1 8 3
0 8 3
1 8 3
2 8 3
3 8 3
-3 9 3
-2 9 3
-1 9 3
0 9 3
1 9 3
2 9 3
-2 10 3
-1 10 3
0 10 3
1 10 3
2 10 3
-2 11 3
-1 11 3
0 11 3
1 11 3
2 11 3
-1 12 3
0 12 3
1 12 3
-4 0 4
4 0 4
-4 1 4
-3 1 4
-2 1 4
2 1 4
3 1 4
4 1 4
-4 2 4
-3 2 4
-2 2 4
2 2 4
3 2 4
4 2 4
-4 3 4
-3 3 4
-2 3 4
2 3 4
3 3 4
4 3 4
-4 4 4
-3 4 4
-2 4 4
1 4 4
2 4 4
3 4 4
4 4 4
-4 5 4
-3 5 4
-1 5 4
0 5 4
1 5 4
2 5 4
3 5 4
4 5 4
-4 6 4
-3 6 4
-2 6 4
-1 6 4
0 6 4
1 6 4
2 6 4
3 6 4
-3 7 4
-2 7 4
-1 7 4
0 7 4
1 7 4
2 7 4
3 7 4
-3 8 4
-2 8 4
-1 8 4
0 8 4
1 8 4
2 8 4
3 8 4
-3 9 4
-2 9 4
-1 9 4
0 9 4
1 9 4
2 9 4
-2 10 4
-1 10 4
1 10 4
2 10 4
-2 11 4
-1 11 4
0 11 4
1 11 4
-1 12 4
3 0 5
3 1 5
4 1 5
3 2 5
4 2 5
-4 3 5
-3 3 5
2 3 5
3 3 5
4 3 5
-4 4 5
-3 4 5
2 4 5
3 4 5
4 4 5
-4 5 5
-3 5 5
-2 5 5
1 5 5
2 5 5
3 5 5
-4 6 5
-3 6 5
-2 6 5
-1 6 5
0 6 5
1 6 5
2 6 5
3 6 5
-3 7 5
-2 7 5
-1 7 5
0 7 5
1 7 5
2 7 5
3 7 5
-3 8 5
-2 8 5
-1 8 5
0 8 5
1 8 5
2 8 5
3 8 5
-3 9 5
-2 9 5
-1 9 5
0 9 5
1 9 5
2 9 5
-2 10 5
-1 10 5
1 10 5
2 10 5
-1 11 5
0 11 5
1 11 5
0 12 5
2 8 6
0 9 6
1 9 6
2 9 6
-1 10 6
0 10 6
1 10 6
0 11 6
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13837988
2 PubChem 7239
