#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/46/2224689.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_2224689
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Chidan Kumar, C. S.'
'Yathirajan, H. S.'
'Narayana, B.'
_publ_section_title
;
 2,4-Dichloro-1-[1-(2,4-dichlorobenzyloxy)ethyl]benzene
;
_journal_coeditor_code           IS2502
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o165
_journal_page_last               o166
_journal_paper_doi               10.1107/S1600536809053422
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H12 Cl4 O'
_chemical_formula_moiety         'C15 H12 Cl4 O'
_chemical_formula_sum            'C15 H12 Cl4 O'
_chemical_formula_weight         350.05
_chemical_name_systematic
;
2,4-Dichloro-1-[1-(2,4-dichlorobenzyloxy)ethyl]benzene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                62.313(3)
_cell_angle_beta                 70.246(4)
_cell_angle_gamma                71.467(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3755(4)
_cell_length_b                   9.9229(4)
_cell_length_c                   9.9667(4)
_cell_measurement_reflns_used    5527
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.4370
_cell_measurement_theta_min      4.7183
_cell_volume                     758.22(6)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_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  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10547
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.52
_diffrn_reflns_theta_min         4.73
_diffrn_standards_decay_%        <2%
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisRed; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0307
_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)+(0.0476P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0800
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                3334
_reflns_number_total             4961
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2502.cif
_cod_data_source_block           I
_cod_original_cell_volume        758.22(5)
_cod_database_code               2224689
_cod_database_fobs_code          2224689
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl Cl1 0.36865(4) 1.29719(4) 0.57705(4) 0.03911(9) Uani d . 1 . .
Cl Cl2 0.69931(4) 1.09520(4) 0.12662(4) 0.03879(10) Uani d . 1 . .
Cl Cl3 0.62657(4) 0.54530(4) 1.05029(5) 0.04802(11) Uani d . 1 . .
Cl Cl4 1.07650(5) 0.37832(4) 1.34956(4) 0.05247(12) Uani d . 1 . .
O O1 0.75079(10) 1.00830(9) 0.81884(9) 0.0308(2) Uani d . 1 . .
C C1 0.65742(14) 1.12007(12) 0.58044(13) 0.0267(2) Uani d . 1 . .
C C2 0.53833(14) 1.19326(12) 0.50167(14) 0.0267(2) Uani d . 1 . .
C C3 0.54921(14) 1.18650(12) 0.36200(13) 0.0281(3) Uani d . 1 . .
H H3A 0.4666 1.2370 0.3100 0.034 Uiso calc R 1 . .
C C4 0.68305(15) 1.10458(13) 0.30135(13) 0.0286(3) Uani d . 1 . .
C C5 0.80410(15) 1.02893(14) 0.37548(14) 0.0323(3) Uani d . 1 . .
H H5A 0.8951 0.9720 0.3324 0.039 Uiso calc R 1 . .
C C6 0.78960(14) 1.03809(14) 0.51481(14) 0.0308(3) Uani d . 1 . .
H H6A 0.8724 0.9869 0.5665 0.037 Uiso calc R 1 . .
C C7 0.64875(15) 1.13389(13) 0.72917(13) 0.0298(3) Uani d . 1 . .
H H7A 0.5404 1.1344 0.7932 0.036 Uiso calc R 1 . .
C C8 0.6967(2) 1.28197(15) 0.69213(17) 0.0428(3) Uani d . 1 . .
H H8A 0.6857 1.2908 0.7892 0.064 Uiso calc R 1 . .
H H8B 0.6307 1.3714 0.6291 0.064 Uiso calc R 1 . .
H H8C 0.8046 1.2794 0.6342 0.064 Uiso calc R 1 . .
C C9 0.69843(15) 0.86580(13) 0.89183(14) 0.0301(3) Uani d . 1 . .
H H9A 0.7024 0.8313 0.8118 0.036 Uiso calc R 1 . .
H H9B 0.5899 0.8804 0.9504 0.036 Uiso calc R 1 . .
C C10 0.79787(14) 0.74457(13) 1.00075(13) 0.0259(2) Uani d . 1 . .
C C11 0.77114(14) 0.59377(14) 1.08286(14) 0.0298(3) Uani d . 1 . .
C C12 0.85496(15) 0.47887(14) 1.19003(14) 0.0330(3) Uani d . 1 . .
H H12A 0.8339 0.3769 1.2447 0.040 Uiso calc R 1 . .
C C13 0.97003(15) 0.51798(14) 1.21437(14) 0.0343(3) Uani d . 1 . .
C C14 1.00324(16) 0.66490(15) 1.13334(15) 0.0354(3) Uani d . 1 . .
H H14A 1.0845 0.6889 1.1500 0.042 Uiso calc R 1 . .
C C15 0.91710(15) 0.77740(14) 1.02725(14) 0.0298(3) Uani d . 1 . .
H H15A 0.9399 0.8787 0.9717 0.036 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O1 C7 . . 112.73(9) ?
C6 C1 C2 . . 117.47(11) ?
C6 C1 C7 . . 120.34(10) ?
C2 C1 C7 . . 122.13(11) ?
C1 C2 C3 . . 122.11(11) ?
C1 C2 Cl1 . . 120.19(9) ?
C3 C2 Cl1 . . 117.69(9) ?
C4 C3 C2 . . 118.14(11) ?
C4 C3 H3A . . 120.9 ?
C2 C3 H3A . . 120.9 ?
C3 C4 C5 . . 122.02(11) ?
C3 C4 Cl2 . . 118.89(9) ?
C5 C4 Cl2 . . 119.09(10) ?
C4 C5 C6 . . 118.40(12) ?
C4 C5 H5A . . 120.8 ?
C6 C5 H5A . . 120.8 ?
C1 C6 C5 . . 121.85(11) ?
C1 C6 H6A . . 119.1 ?
C5 C6 H6A . . 119.1 ?
O1 C7 C8 . . 106.63(10) ?
O1 C7 C1 . . 111.59(10) ?
C8 C7 C1 . . 110.86(10) ?
O1 C7 H7A . . 109.2 ?
C8 C7 H7A . . 109.2 ?
C1 C7 H7A . . 109.2 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O1 C9 C10 . . 110.07(9) ?
O1 C9 H9A . . 109.6 ?
C10 C9 H9A . . 109.6 ?
O1 C9 H9B . . 109.6 ?
C10 C9 H9B . . 109.6 ?
H9A C9 H9B . . 108.2 ?
C11 C10 C15 . . 117.12(11) ?
C11 C10 C9 . . 120.55(10) ?
C15 C10 C9 . . 122.31(10) ?
C12 C11 C10 . . 123.01(11) ?
C12 C11 Cl3 . . 118.03(9) ?
C10 C11 Cl3 . . 118.96(9) ?
C13 C12 C11 . . 117.65(11) ?
C13 C12 H12A . . 121.2 ?
C11 C12 H12A . . 121.2 ?
C14 C13 C12 . . 121.51(11) ?
C14 C13 Cl4 . . 119.22(10) ?
C12 C13 Cl4 . . 119.27(10) ?
C13 C14 C15 . . 119.47(12) ?
C13 C14 H14A . . 120.3 ?
C15 C14 H14A . . 120.3 ?
C14 C15 C10 . . 121.21(11) ?
C14 C15 H15A . . 119.4 ?
C10 C15 H15A . . 119.4 ?
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
Cl1 C2 . 1.7401(13) ?
Cl2 C4 . 1.7398(12) ?
Cl3 C11 . 1.7409(12) ?
Cl4 C13 . 1.7398(12) ?
O1 C9 . 1.4189(14) ?
O1 C7 . 1.4325(13) ?
C1 C6 . 1.3896(17) ?
C1 C2 . 1.3920(16) ?
C1 C7 . 1.5242(16) ?
C2 C3 . 1.3926(16) ?
C3 C4 . 1.3770(18) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.3811(17) ?
C5 C6 . 1.3917(17) ?
C5 H5A . 0.9500 ?
C6 H6A . 0.9500 ?
C7 C8 . 1.5170(16) ?
C7 H7A . 1.0000 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.5008(16) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.3905(16) ?
C10 C15 . 1.3915(17) ?
C11 C12 . 1.3873(16) ?
C12 C13 . 1.3799(18) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.3780(18) ?
C14 C15 . 1.3869(17) ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C12 H12A Cg1 1_546 0.95 2.97 3.8888(15) 162
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
C6 C1 C2 C3 . . . . -0.25(17) ?
C7 C1 C2 C3 . . . . 176.98(10) ?
C6 C1 C2 Cl1 . . . . 179.61(9) ?
C7 C1 C2 Cl1 . . . . -3.16(15) ?
C1 C2 C3 C4 . . . . -0.16(17) ?
Cl1 C2 C3 C4 . . . . 179.98(8) ?
C2 C3 C4 C5 . . . . 0.65(17) ?
C2 C3 C4 Cl2 . . . . -179.79(8) ?
C3 C4 C5 C6 . . . . -0.72(18) ?
Cl2 C4 C5 C6 . . . . 179.73(9) ?
C2 C1 C6 C5 . . . . 0.18(18) ?
C7 C1 C6 C5 . . . . -177.10(11) ?
C4 C5 C6 C1 . . . . 0.28(19) ?
C9 O1 C7 C8 . . . . 166.43(10) ?
C9 O1 C7 C1 . . . . -72.37(12) ?
C6 C1 C7 O1 . . . . -24.78(15) ?
C2 C1 C7 O1 . . . . 158.07(10) ?
C6 C1 C7 C8 . . . . 93.92(14) ?
C2 C1 C7 C8 . . . . -83.23(14) ?
C7 O1 C9 C10 . . . . -172.27(9) ?
O1 C9 C10 C11 . . . . -178.34(11) ?
O1 C9 C10 C15 . . . . 3.20(17) ?
C15 C10 C11 C12 . . . . 1.43(19) ?
C9 C10 C11 C12 . . . . -177.11(12) ?
C15 C10 C11 Cl3 . . . . -178.37(10) ?
C9 C10 C11 Cl3 . . . . 3.10(16) ?
C10 C11 C12 C13 . . . . -0.2(2) ?
Cl3 C11 C12 C13 . . . . 179.57(10) ?
C11 C12 C13 C14 . . . . -1.24(19) ?
C11 C12 C13 Cl4 . . . . 179.17(10) ?
C12 C13 C14 C15 . . . . 1.4(2) ?
Cl4 C13 C14 C15 . . . . -178.97(10) ?
C13 C14 C15 C10 . . . . -0.2(2) ?
C11 C10 C15 C14 . . . . -1.21(18) ?
C9 C10 C15 C14 . . . . 177.29(12) ?
