#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/27/2102737.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_2102737
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          248.3
_chemical_name_common
;
 1,3-dichlorobenzene
 meta-dichlorobenzene
;
_chemical_name_systematic
;
 1,3-dichlorobenzene
 meta-dichlorobenzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 93.098(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   3.9163(6)
_cell_length_b                   12.532(5)
_cell_length_c                   25.849(5)
_cell_measurement_reflns_used    2167
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.57
_cell_measurement_theta_min      2.26
_cell_volume                     1266.8(6)
_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 0.357
_diffrn_measured_fraction_theta_max 0.357
_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  0.0910
_diffrn_reflns_av_sigmaI/netI    0.0890
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4205
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_correction_T_min  0.40
_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    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.186
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.468
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         800
_refine_ls_number_restraints     222
_refine_ls_restrained_S_all      1.294
_refine_ls_R_factor_all          0.1726
_refine_ls_R_factor_gt           0.1091
_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)+(0.0230P)²+1.9560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                627
_reflns_number_total             800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            so5006.cif
_cod_data_source_block           mDCB
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2102737
_cod_database_fobs_code          2102737
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.2856(7) 0.5602(4) 0.09131(11) 0.076(2) Uani d U 1
Cl Cl2 -0.2206(7) 0.2061(4) 0.17370(10) 0.0707(19) Uani d U 1
Cl Cl3 0.4221(7) 1.0049(4) 0.25859(9) 0.076(2) Uani d U 1
Cl Cl4 0.3740(7) 0.9352(4) 0.05431(10) 0.0797(19) Uani d U 1
C C1 0.153(2) 0.4284(15) 0.0842(4) 0.050(4) Uani d DU 1
C C2 0.030(2) 0.3750(13) 0.1259(4) 0.045(4) Uani d DU 1
H H2 0.0177 0.4096 0.1576 0.054 Uiso calc R 1
C C3 -0.074(2) 0.2716(13) 0.1208(4) 0.045(4) Uani d DU 1
C C4 -0.050(2) 0.2198(12) 0.0746(4) 0.057(4) Uani d DU 1
H H4 -0.1155 0.1487 0.0710 0.069 Uiso calc R 1
C C5 0.074(3) 0.2752(13) 0.0334(4) 0.063(4) Uani d DU 1
H H5 0.0860 0.2406 0.0017 0.076 Uiso calc R 1
C C6 0.180(3) 0.3784(14) 0.0373(4) 0.061(4) Uani d DU 1
H H6 0.2684 0.4137 0.0093 0.074 Uiso calc R 1
C C7 0.510(2) 0.9219(13) 0.2060(4) 0.048(4) Uani d DU 1
C C8 0.410(2) 0.9590(13) 0.1571(3) 0.047(4) Uani d DU 1
H H8 0.2969 1.0235 0.1516 0.057 Uiso calc R 1
C C9 0.493(2) 0.8925(13) 0.1168(4) 0.048(4) Uani d DU 1
C C10 0.664(3) 0.7977(13) 0.1237(4) 0.058(4) Uani d DU 1
H H10 0.7198 0.7566 0.0954 0.069 Uiso calc R 1
C C11 0.752(3) 0.7650(13) 0.1732(4) 0.062(4) Uani d DU 1
H H11 0.8634 0.7001 0.1788 0.074 Uiso calc R 1
C C12 0.677(3) 0.8283(13) 0.2149(4) 0.057(4) Uani d DU 1
H H12 0.7392 0.8070 0.2486 0.069 Uiso calc R 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'
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
C2 C3 Cl2 119.2(9) y
C3 C2 C1 120.1(12) y
C5 C6 C1 117.5(13) y
C2 C1 Cl1 119.5(10) y
C4 C3 Cl2 120.6(11) y
C2 C3 C4 120.1(11) y
C6 C5 C4 122.7(13) y
C3 C4 C5 118.6(14) y
C6 C1 Cl1 119.4(10) y
C6 C1 C2 121.1(15) y
C1 C2 H2 120.0 ?
C1 C6 H6 121.3 ?
C3 C2 H2 120.0 ?
C3 C4 H4 120.7 ?
C4 C5 H5 118.7 ?
C5 C4 H4 120.7 ?
C5 C6 H6 121.3 ?
C6 C5 H5 118.7 ?
C8 C9 Cl4 116.8(11) y
C7 C8 C9 114.8(12) y
C7 C12 C11 119.0(12) y
C8 C7 Cl3 116.8(11) y
C10 C9 Cl4 119.4(9) y
C10 C9 C8 123.8(12) y
C10 C11 C12 120.2(14) y
C11 C10 C9 118.5(12) y
C12 C7 Cl3 119.5(9) y
C12 C7 C8 123.7(12) y
C7 C8 H8 122.6 ?
C7 C12 H12 120.5 ?
C9 C8 H8 122.6 ?
C9 C10 H10 120.7 ?
C10 C11 H11 119.9 ?
C11 C10 H10 120.7 ?
C11 C12 H12 120.5 ?
C12 C11 H11 119.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.739(17) y
C1 C2 1.380(13) y
C1 C6 1.373(13) y
Cl2 C3 1.719(12) y
C2 C3 1.362(15) y
C3 C4 1.368(12) y
C4 C5 1.382(13) y
C5 C6 1.360(16) y
C2 H2 0.9300 ?
C4 H4 0.9300 ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
Cl3 C7 1.761(13) y
C7 C8 1.383(11) y
C7 C12 1.357(15) y
Cl4 C9 1.741(11) y
C8 C9 1.384(13) y
C9 C10 1.372(15) y
C10 C11 1.369(11) y
C11 C12 1.383(13) y
C8 H8 0.9300 ?
C10 H10 0.9300 ?
C11 H11 0.9300 ?
C12 H12 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 1.5(17)
C1 C2 C3 Cl2 179.0(7)
C2 C1 C6 C5 1.5(18)
C2 C3 C4 C5 -1.5(17)
C3 C4 C5 C6 1.5(18)
C4 C5 C6 C1 -2(2)
C6 C1 C2 C3 -1.5(16)
C7 C8 C9 C10 -1.0(17)
C7 C8 C9 Cl4 180.0(8)
C8 C7 C12 C11 -0.4(19)
C8 C9 C10 C11 1.7(19)
C9 C10 C11 C12 -1.7(18)
C10 C11 C12 C7 1.1(17)
Cl1 C1 C2 C3 -179.9(10)
Cl1 C1 C6 C5 179.9(11)
Cl2 C3 C4 C5 -178.9(8)
C12 C7 C8 C9 0.3(16)
Cl3 C7 C8 C9 178.2(8)
Cl3 C7 C12 C11 -178.2(8)
Cl4 C9 C10 C11 -179.3(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13857694
