#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/75/2217526.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_2217526
loop_
_publ_author_name
'Betz, Richard'
'Klüfers, Peter'
'Reichvilser, Moritz M.'
_publ_section_title
;
 Dichlorodiphenoxymethane
;
_journal_coeditor_code           HG2358
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o354
_journal_page_last               o354
_journal_paper_doi               10.1107/S160053680706789X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H10 Cl2 O2'
_chemical_formula_moiety         'C13 H10 Cl2 O2'
_chemical_formula_sum            'C13 H10 Cl2 O2'
_chemical_formula_weight         269.11
_chemical_name_common            Dichlorodiphenoxymethane
_chemical_name_systematic        Dichlorodiphenoxymethane
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_cell_angle_alpha                90.00
_cell_angle_beta                 114.751(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8380(4)
_cell_length_b                   5.8973(2)
_cell_length_c                   14.2517(4)
_cell_measurement_reflns_used    12368
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     1208.85(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2004)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9193
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.288
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0373
_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)+(0.0387P)²+0.3721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                2138
_reflns_number_total             2766
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2358.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217526
_cod_database_fobs_code          2217526
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 0.22903(3) 0.81935(8) -0.00008(4) 0.04218(16) Uani d . 1
Cl Cl2 0.16437(3) 0.38393(9) 0.03397(4) 0.04247(16) Uani d . 1
O O1 0.26019(8) 0.4390(2) -0.07857(9) 0.0370(3) Uani d . 1
O O2 0.34125(8) 0.4761(2) 0.08404(9) 0.0367(3) Uani d . 1
C C1 0.25543(12) 0.5198(3) 0.00839(13) 0.0327(4) Uani d . 1
C C2 0.18098(12) 0.4454(3) -0.17458(13) 0.0323(4) Uani d . 1
C C3 0.12316(13) 0.2594(3) -0.20312(14) 0.0367(4) Uani d . 1
H H3 0.1345 0.1336 -0.1578 0.044 Uiso calc R 1
C C4 0.04817(13) 0.2588(4) -0.29911(14) 0.0379(4) Uani d . 1
H H4 0.0071 0.1327 -0.3198 0.046 Uiso calc R 1
C C5 0.03320(13) 0.4419(3) -0.36477(14) 0.0371(4) Uani d . 1
H H5 -0.0187 0.4424 -0.4301 0.045 Uiso calc R 1
C C6 0.09367(13) 0.6242(3) -0.33543(14) 0.0394(5) Uani d . 1
H H6 0.0836 0.7484 -0.3813 0.047 Uiso calc R 1
C C7 0.16881(13) 0.6273(3) -0.23968(14) 0.0375(4) Uani d . 1
H H7 0.2108 0.7516 -0.2194 0.045 Uiso calc R 1
C C8 0.36336(11) 0.5446(3) 0.18686(14) 0.0332(4) Uani d . 1
C C9 0.34856(13) 0.3947(3) 0.25296(15) 0.0404(5) Uani d . 1
H H9 0.3195 0.2525 0.2286 0.048 Uiso calc R 1
C C10 0.37686(13) 0.4557(4) 0.35513(16) 0.0448(5) Uani d . 1
H H10 0.3670 0.3547 0.4015 0.054 Uiso calc R 1
C C11 0.41948(12) 0.6623(4) 0.39062(15) 0.0418(5) Uani d . 1
H H11 0.4382 0.7039 0.4609 0.050 Uiso calc R 1
C C12 0.43477(13) 0.8085(3) 0.32332(15) 0.0411(5) Uani d . 1
H H12 0.4645 0.9500 0.3477 0.049 Uiso calc R 1
C C13 0.40687(12) 0.7493(3) 0.22053(15) 0.0377(4) Uani d . 1
H H13 0.4177 0.8486 0.1742 0.045 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'
O O 0.0106 0.0060 '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 O1 C2 120.43(13) ?
C1 O2 C8 119.92(13) ?
O1 C1 O2 103.77(13) y
O1 C1 Cl1 112.41(12) ?
O2 C1 Cl1 111.39(13) ?
O1 C1 Cl2 112.36(12) ?
O2 C1 Cl2 111.80(12) ?
Cl1 C1 Cl2 105.29(9) y
C3 C2 C7 122.22(17) ?
C3 C2 O1 118.32(16) ?
C7 C2 O1 119.22(16) ?
C2 C3 C4 118.85(18) ?
C2 C3 H3 120.6 ?
C4 C3 H3 120.6 ?
C5 C4 C3 119.95(18) ?
C5 C4 H4 120.0 ?
C3 C4 H4 120.0 ?
C4 C5 C6 120.11(18) ?
C4 C5 H5 119.9 ?
C6 C5 H5 119.9 ?
C5 C6 C7 120.59(18) ?
C5 C6 H6 119.7 ?
C7 C6 H6 119.7 ?
C2 C7 C6 118.23(18) ?
C2 C7 H7 120.9 ?
C6 C7 H7 120.9 ?
C13 C8 C9 121.85(18) ?
C13 C8 O2 118.89(16) ?
C9 C8 O2 118.98(17) ?
C10 C9 C8 118.69(19) ?
C10 C9 H9 120.7 ?
C8 C9 H9 120.7 ?
C9 C10 C11 120.60(19) ?
C9 C10 H10 119.7 ?
C11 C10 H10 119.7 ?
C10 C11 C12 119.71(19) ?
C10 C11 H11 120.1 ?
C12 C11 H11 120.1 ?
C11 C12 C13 120.33(19) ?
C11 C12 H12 119.8 ?
C13 C12 H12 119.8 ?
C8 C13 C12 118.81(18) ?
C8 C13 H13 120.6 ?
C12 C13 H13 120.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1.8078(18) ?
Cl2 C1 1.8154(18) ?
O1 C1 1.359(2) y
O1 C2 1.418(2) ?
O2 C1 1.360(2) y
O2 C8 1.415(2) ?
C2 C3 1.377(3) ?
C2 C7 1.378(3) ?
C3 C4 1.386(3) ?
C3 H3 0.9500 ?
C4 C5 1.383(3) ?
C4 H4 0.9500 ?
C5 C6 1.383(3) ?
C5 H5 0.9500 ?
C6 C7 1.385(3) ?
C6 H6 0.9500 ?
C7 H7 0.9500 ?
C8 C13 1.373(3) ?
C8 C9 1.381(3) ?
C9 C10 1.380(3) ?
C9 H9 0.9500 ?
C10 C11 1.382(3) ?
C10 H10 0.9500 ?
C11 C12 1.384(3) ?
C11 H11 0.9500 ?
C12 C13 1.386(3) ?
C12 H12 0.9500 ?
C13 H13 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
C3 H3 Cl1 1_545 0.95 2.81 3.723(2) 161
C10 H10 O1 4_566 0.95 2.52 3.345(3) 145
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
C2 O1 C1 O2 177.16(14)
C2 O1 C1 Cl1 -62.36(19)
C2 O1 C1 Cl2 56.20(19)
C8 O2 C1 O1 178.00(15)
C8 O2 C1 Cl1 56.83(19)
C8 O2 C1 Cl2 -60.67(19)
C1 O1 C2 C3 -91.8(2)
C1 O1 C2 C7 93.7(2)
C7 C2 C3 C4 -2.4(3)
O1 C2 C3 C4 -176.73(15)
C2 C3 C4 C5 0.8(3)
C3 C4 C5 C6 0.9(3)
C4 C5 C6 C7 -1.0(3)
C3 C2 C7 C6 2.3(3)
O1 C2 C7 C6 176.56(16)
C5 C6 C7 C2 -0.6(3)
C1 O2 C8 C13 -94.4(2)
C1 O2 C8 C9 91.6(2)
C13 C8 C9 C10 1.3(3)
O2 C8 C9 C10 175.07(16)
C8 C9 C10 C11 -0.2(3)
C9 C10 C11 C12 -0.7(3)
C10 C11 C12 C13 0.5(3)
C9 C8 C13 C12 -1.4(3)
O2 C8 C13 C12 -175.20(16)
C11 C12 C13 C8 0.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4291793
