#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220709.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_2220709
loop_
_publ_author_name
'Cantillana, Tatiana'
'Eriksson, Lars'
_publ_section_title
;
 (2S)-1,1-Dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane
;
_journal_coeditor_code           BQ2116
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o297
_journal_paper_doi               10.1107/S160053680804405X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H10 Cl4'
_chemical_formula_moiety         'C14 H10 Cl4'
_chemical_formula_sum            'C14 H10 Cl4'
_chemical_formula_weight         320.02
_chemical_name_systematic
;
(2S)-1,1-Dichloro-2-(2-chlorophenyl)-2-(4-chlorophenyl)ethane
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
'Manual editing of the cif file from SHELXL-97'
_cell_angle_alpha                90.00
_cell_angle_beta                 103.5490(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.13530(10)
_cell_length_b                   12.0715(2)
_cell_length_c                   9.4525(2)
_cell_measurement_reflns_used    11963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.14
_cell_measurement_theta_min      3.80
_cell_volume                     680.59(2)
_computing_cell_refinement       'Crysalis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'Crysalis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'Crysalis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'DIAMOND (Bergerhoff, 1996)'
_computing_publication_material
'PLATON (Spek, 2003) and SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.54
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type
'Oxford Diffraction Xcalibur-3 κ-diffractometer with Sapphire-III CCD'
_diffrn_measurement_method       'ω scans at different φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18569
_diffrn_reflns_theta_full        32.24
_diffrn_reflns_theta_max         32.24
_diffrn_reflns_theta_min         3.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.306
_refine_ls_abs_structure_details 'Flack (1983), 1755 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0259
_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)+(0.0358P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0598
_reflns_number_gt                3935
_reflns_number_total             4258
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bq2116.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2220709
_cod_database_fobs_code          2220709
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_disorder_assembly
_atom_site_disorder_group
C C1 0.5723(2) 0.58327(13) 0.35281(15) 0.0153(3) Uani d . 1 . .
H H1 0.4179 0.5513 0.3360 0.018 Uiso calc R 1 . .
C C2 0.5682(2) 0.70231(12) 0.40708(16) 0.0136(3) Uani d . 1 . .
H H2 0.7233 0.7330 0.4219 0.016 Uiso calc R 1 . .
Cl Cl1 0.75951(6) 0.50047(3) 0.48348(4) 0.02031(8) Uani d . 1 . .
Cl Cl2 0.66068(6) 0.58092(3) 0.18581(4) 0.02172(9) Uani d . 1 . .
C C3 0.4118(2) 0.77539(12) 0.29597(15) 0.0143(3) Uani d . 1 . .
C C4 0.4896(3) 0.87540(13) 0.25332(16) 0.0178(3) Uani d . 1 . .
H H4 0.6434 0.8943 0.2871 0.021 Uiso calc R 1 . .
C C5 0.3459(3) 0.94815(14) 0.16209(16) 0.0196(3) Uani d . 1 . .
H H5 0.4006 1.0162 0.1335 0.024 Uiso calc R 1 . .
C C6 0.1222(3) 0.92006(14) 0.11361(15) 0.0174(3) Uani d . 1 . .
C C7 0.0412(3) 0.81928(14) 0.15077(17) 0.0197(3) Uani d . 1 . .
H H7 -0.1116 0.7996 0.1141 0.024 Uiso calc R 1 . .
C C8 0.1859(2) 0.74824(14) 0.24185(17) 0.0185(3) Uani d . 1 . .
H H8 0.1310 0.6796 0.2683 0.022 Uiso calc R 1 . .
Cl Cl3 -0.06289(6) 1.01373(3) 0.00690(4) 0.02230(9) Uani d . 1 . .
C C9 0.5012(2) 0.70772(12) 0.55256(16) 0.0149(3) Uani d . 1 . .
C C10 0.3199(3) 0.64714(13) 0.57858(16) 0.0177(3) Uani d . 1 . .
H H10 0.2424 0.5974 0.5062 0.021 Uiso calc R 1 . .
C C11 0.2503(3) 0.65801(14) 0.70765(17) 0.0192(3) Uani d . 1 . .
H H11 0.1263 0.6162 0.7223 0.023 Uiso calc R 1 . .
C C12 0.3609(3) 0.72933(15) 0.81459(17) 0.0212(3) Uani d . 1 . .
H H12 0.3129 0.7366 0.9026 0.025 Uiso calc R 1 . .
C C13 0.5417(3) 0.79019(14) 0.79373(17) 0.0207(3) Uani d . 1 . .
H H13 0.6192 0.8389 0.8674 0.025 Uiso calc R 1 . .
C C14 0.6088(2) 0.77922(13) 0.66334(16) 0.0157(3) Uani d . 1 . .
Cl Cl4 0.83309(6) 0.86142(3) 0.64058(4) 0.02012(8) Uani d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 Cl1 . . 110.68(10) ?
C2 C1 Cl2 . . 110.12(10) ?
Cl1 C1 Cl2 . . 108.88(8) ?
C2 C1 H1 . . 109.0 ?
Cl1 C1 H1 . . 109.0 ?
Cl2 C1 H1 . . 109.0 ?
C9 C2 C3 . . 109.67(11) ?
C9 C2 C1 . . 111.82(12) ?
C3 C2 C1 . . 111.69(12) ?
C9 C2 H2 . . 107.8 ?
C3 C2 H2 . . 107.8 ?
C1 C2 H2 . . 107.8 ?
C4 C3 C8 . . 118.35(14) ?
C4 C3 C2 . . 119.83(13) ?
C8 C3 C2 . . 121.69(13) ?
C5 C4 C3 . . 121.07(14) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C6 C5 C4 . . 119.09(15) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C5 C6 C7 . . 121.11(15) ?
C5 C6 Cl3 . . 119.54(13) ?
C7 C6 Cl3 . . 119.33(12) ?
C8 C7 C6 . . 119.01(14) ?
C8 C7 H7 . . 120.5 ?
C6 C7 H7 . . 120.5 ?
C7 C8 C3 . . 121.31(14) ?
C7 C8 H8 . . 119.3 ?
C3 C8 H8 . . 119.3 ?
C14 C9 C10 . . 116.49(13) ?
C14 C9 C2 . . 121.46(13) ?
C10 C9 C2 . . 121.92(13) ?
C11 C10 C9 . . 121.65(15) ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
C12 C11 C10 . . 120.19(15) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 120.04(14) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C12 C13 C14 . . 119.25(15) ?
C12 C13 H13 . . 120.4 ?
C14 C13 H13 . . 120.4 ?
C13 C14 C9 . . 122.37(15) ?
C13 C14 Cl4 . . 117.29(12) ?
C9 C14 Cl4 . . 120.33(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.528(2) ?
C1 Cl1 . 1.7831(15) ?
C1 Cl2 . 1.7855(14) ?
C1 H1 . 1.0000 ?
C2 C9 . 1.526(2) ?
C2 C3 . 1.526(2) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.392(2) ?
C3 C8 . 1.399(2) ?
C4 C5 . 1.391(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.383(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.390(2) ?
C6 Cl3 . 1.7462(16) ?
C7 C8 . 1.381(2) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C14 . 1.398(2) ?
C9 C10 . 1.400(2) ?
C10 C11 . 1.390(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.379(2) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.382(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.394(2) ?
C13 H13 . 0.9500 ?
C14 Cl4 . 1.7503(16) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 Cl4 3.4370(5) . 2_746 y
Cl2 Cl3 3.4888(5) . 2_645 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cl1 C1 C2 C9 . . . . -57.58(13) ?
Cl2 C1 C2 C9 . . . . -178.02(9) ?
Cl1 C1 C2 C3 . . . . 179.08(9) ?
Cl2 C1 C2 C3 . . . . 58.64(13) ?
C9 C2 C3 C4 . . . . 107.05(15) ?
C1 C2 C3 C4 . . . . -128.40(14) ?
C9 C2 C3 C8 . . . . -68.77(17) ?
C1 C2 C3 C8 . . . . 55.78(18) ?
C8 C3 C4 C5 . . . . 1.6(2) ?
C2 C3 C4 C5 . . . . -174.36(14) ?
C3 C4 C5 C6 . . . . 0.1(2) ?
C4 C5 C6 C7 . . . . -2.1(2) ?
C4 C5 C6 Cl3 . . . . 176.66(12) ?
C5 C6 C7 C8 . . . . 2.3(2) ?
Cl3 C6 C7 C8 . . . . -176.42(12) ?
C6 C7 C8 C3 . . . . -0.6(2) ?
C4 C3 C8 C7 . . . . -1.3(2) ?
C2 C3 C8 C7 . . . . 174.53(14) ?
C3 C2 C9 C14 . . . . -96.67(15) ?
C1 C2 C9 C14 . . . . 138.85(14) ?
C3 C2 C9 C10 . . . . 78.99(17) ?
C1 C2 C9 C10 . . . . -45.48(18) ?
C14 C9 C10 C11 . . . . 0.2(2) ?
C2 C9 C10 C11 . . . . -175.63(14) ?
C9 C10 C11 C12 . . . . -0.3(2) ?
C10 C11 C12 C13 . . . . -0.1(2) ?
C11 C12 C13 C14 . . . . 0.6(2) ?
C12 C13 C14 C9 . . . . -0.7(2) ?
C12 C13 C14 Cl4 . . . . 178.08(12) ?
C10 C9 C14 C13 . . . . 0.3(2) ?
C2 C9 C14 C13 . . . . 176.15(14) ?
C10 C9 C14 Cl4 . . . . -178.44(11) ?
C2 C9 C14 Cl4 . . . . -2.55(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5036084
