#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/59/2225945.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_2225945
loop_
_publ_author_name
'Li, Xueshu'
'Parkin, Sean'
'Duffel, Michael W.'
'Robertson, Larry W.'
'Lehmler, Hans-Joachim'
_publ_section_title
;
 Biphenyl-4-yl 2,2,2-trichloroethyl sulfate
;
_journal_coeditor_code           OM2330
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1073
_journal_paper_doi               10.1107/S1600536810012845
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H11 Cl3 O4 S'
_chemical_formula_moiety         'C14 H11 Cl3 O4 S'
_chemical_formula_sum            'C14 H11 Cl3 O4 S'
_chemical_formula_weight         381.64
_chemical_name_systematic
;
Biphenyl-4-yl 2,2,2-trichloroethyl sulfate
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.181(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5761(2)
_cell_length_b                   5.8272(2)
_cell_length_c                   35.2679(11)
_cell_measurement_reflns_used    19102
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.00
_cell_volume                     1556.98(8)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELX97 (Sheldrick, 2008) and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_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  0.0787
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            15429
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker Nonius, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0538
_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)+(0.0617P)²+1.4460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                1939
_reflns_number_total             3041
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2330.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2225945
_cod_database_fobs_code          2225945
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.57446(13) 0.92450(18) 0.59262(3) 0.0208(3) Uani d . 1 . .
O O1 0.6710(3) 0.7616(5) 0.62196(7) 0.0220(7) Uani d . 1 . .
O O2 0.3875(3) 0.8117(5) 0.58864(7) 0.0209(6) Uani d . 1 . .
O O3 0.6713(4) 0.8999(5) 0.55880(7) 0.0261(7) Uani d . 1 . .
O O4 0.5421(4) 1.1419(5) 0.60895(7) 0.0261(7) Uani d . 1 . .
Cl Cl1 0.21565(14) 0.28054(18) 0.52992(3) 0.0281(3) Uani d . 1 . .
Cl Cl2 0.03163(13) 0.6724(2) 0.56132(3) 0.0289(3) Uani d . 1 . .
Cl Cl3 0.29160(14) 0.73955(18) 0.50317(3) 0.0260(3) Uani d . 1 . .
C C1 0.5167(5) 0.7417(7) 0.73623(11) 0.0193(9) Uani d . 1 . .
C C2 0.4726(5) 0.5655(7) 0.71089(11) 0.0234(10) Uani d . 1 . .
H H2 0.4087 0.4365 0.7199 0.028 Uiso calc R 1 . .
C C3 0.5198(6) 0.5746(7) 0.67315(10) 0.0248(10) Uani d . 1 . .
H H3 0.4888 0.4539 0.6563 0.030 Uiso calc R 1 . .
C C4 0.6121(5) 0.7612(7) 0.66051(10) 0.0192(9) Uani d . 1 . .
C C5 0.6597(5) 0.9377(8) 0.68381(11) 0.0262(10) Uani d . 1 . .
H H5 0.7243 1.0650 0.6743 0.031 Uiso calc R 1 . .
C C6 0.6116(5) 0.9270(7) 0.72177(11) 0.0242(10) Uani d . 1 . .
H H6 0.6441 1.0489 0.7383 0.029 Uiso calc R 1 . .
C C7 0.3776(5) 0.5798(7) 0.57323(10) 0.0202(9) Uani d . 1 . .
H H7A 0.3497 0.4696 0.5937 0.024 Uiso calc R 1 . .
H H7B 0.4928 0.5364 0.5621 0.024 Uiso calc R 1 . .
C C8 0.2351(5) 0.5715(7) 0.54294(10) 0.0203(9) Uani d . 1 . .
C C1' 0.4713(5) 0.7278(7) 0.77748(10) 0.0188(9) Uani d . 1 . .
C C2' 0.5201(6) 0.9018(7) 0.80282(11) 0.0268(10) Uani d . 1 . .
H H2' 0.5773 1.0352 0.7934 0.032 Uiso calc R 1 . .
C C3' 0.4867(6) 0.8833(8) 0.84125(12) 0.0304(11) Uani d . 1 . .
H H3' 0.5219 1.0033 0.8579 0.037 Uiso calc R 1 . .
C C4' 0.4027(5) 0.6923(8) 0.85568(11) 0.0265(10) Uani d . 1 . .
H H4' 0.3811 0.6788 0.8821 0.032 Uiso calc R 1 . .
C C5' 0.3503(6) 0.5199(8) 0.83080(11) 0.0330(11) Uani d . 1 . .
H H5' 0.2903 0.3887 0.8402 0.040 Uiso calc R 1 . .
C C6' 0.3851(5) 0.5385(8) 0.79256(11) 0.0305(11) Uani d . 1 . .
H H6' 0.3489 0.4184 0.7761 0.037 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'
S S 0.1246 0.1234 '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
O3 S1 O4 . . 121.83(18) ?
O3 S1 O2 . . 110.75(16) ?
O4 S1 O2 . . 104.74(16) ?
O3 S1 O1 . . 104.57(16) ?
O4 S1 O1 . . 110.58(15) ?
O2 S1 O1 . . 102.89(15) ?
C4 O1 S1 . . 118.5(2) ?
C7 O2 S1 . . 117.8(2) ?
C6 C1 C2 . . 117.1(4) ?
C6 C1 C1' . . 121.1(4) ?
C2 C1 C1' . . 121.7(4) ?
C3 C2 C1 . . 121.7(4) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
C4 C3 C2 . . 118.6(4) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C5 C4 C3 . . 122.5(4) ?
C5 C4 O1 . . 119.2(4) ?
C3 C4 O1 . . 118.2(3) ?
C4 C5 C6 . . 118.5(4) ?
C4 C5 H5 . . 120.8 ?
C6 C5 H5 . . 120.8 ?
C5 C6 C1 . . 121.6(4) ?
C5 C6 H6 . . 119.2 ?
C1 C6 H6 . . 119.2 ?
O2 C7 C8 . . 109.1(3) ?
O2 C7 H7A . . 109.9 ?
C8 C7 H7A . . 109.9 ?
O2 C7 H7B . . 109.9 ?
C8 C7 H7B . . 109.9 ?
H7A C7 H7B . . 108.3 ?
C7 C8 Cl1 . . 105.8(3) ?
C7 C8 Cl3 . . 111.6(3) ?
Cl1 C8 Cl3 . . 110.3(2) ?
C7 C8 Cl2 . . 110.5(3) ?
Cl1 C8 Cl2 . . 110.0(2) ?
Cl3 C8 Cl2 . . 108.6(2) ?
C6' C1' C2' . . 117.0(4) ?
C6' C1' C1 . . 121.6(4) ?
C2' C1' C1 . . 121.3(4) ?
C3' C2' C1' . . 121.3(4) ?
C3' C2' H2' . . 119.3 ?
C1' C2' H2' . . 119.3 ?
C4' C3' C2' . . 120.7(4) ?
C4' C3' H3' . . 119.7 ?
C2' C3' H3' . . 119.7 ?
C3' C4' C5' . . 118.7(4) ?
C3' C4' H4' . . 120.6 ?
C5' C4' H4' . . 120.6 ?
C6' C5' C4' . . 120.4(4) ?
C6' C5' H5' . . 119.8 ?
C4' C5' H5' . . 119.8 ?
C5' C6' C1' . . 121.9(4) ?
C5' C6' H6' . . 119.1 ?
C1' C6' H6' . . 119.1 ?
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
S1 O3 . 1.410(3) ?
S1 O4 . 1.414(3) ?
S1 O2 . 1.567(3) ?
S1 O1 . 1.582(3) ?
O1 C4 . 1.432(4) ?
O2 C7 . 1.459(5) ?
Cl1 C8 . 1.762(4) ?
Cl2 C8 . 1.774(4) ?
Cl3 C8 . 1.765(4) ?
C1 C6 . 1.395(6) ?
C1 C2 . 1.401(5) ?
C1 C1' . 1.498(5) ?
C2 C3 . 1.380(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.368(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.364(5) ?
C5 C6 . 1.390(5) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.518(5) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C1' C6' . 1.389(6) ?
C1' C2' . 1.400(5) ?
C2' C3' . 1.384(5) ?
C2' H2' . 0.9500 ?
C3' C4' . 1.380(6) ?
C3' H3' . 0.9500 ?
C4' C5' . 1.391(6) ?
C4' H4' . 0.9500 ?
C5' C6' . 1.379(5) ?
C5' H5' . 0.9500 ?
C6' H6' . 0.9500 ?
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
O3 S1 O1 C4 . . . . 175.2(3) ?
O4 S1 O1 C4 . . . . 42.4(3) ?
O2 S1 O1 C4 . . . . -69.0(3) ?
O3 S1 O2 C7 . . . . 48.4(3) ?
O4 S1 O2 C7 . . . . -178.5(2) ?
O1 S1 O2 C7 . . . . -62.8(3) ?
C6 C1 C2 C3 . . . . -0.4(6) ?
C1' C1 C2 C3 . . . . -177.7(4) ?
C1 C2 C3 C4 . . . . 0.1(6) ?
C2 C3 C4 C5 . . . . 0.3(6) ?
C2 C3 C4 O1 . . . . 175.7(3) ?
S1 O1 C4 C5 . . . . -77.2(4) ?
S1 O1 C4 C3 . . . . 107.2(4) ?
C3 C4 C5 C6 . . . . -0.3(6) ?
O1 C4 C5 C6 . . . . -175.7(3) ?
C4 C5 C6 C1 . . . . -0.1(6) ?
C2 C1 C6 C5 . . . . 0.4(6) ?
C1' C1 C6 C5 . . . . 177.7(4) ?
S1 O2 C7 C8 . . . . -132.5(3) ?
O2 C7 C8 Cl1 . . . . -173.5(2) ?
O2 C7 C8 Cl3 . . . . 66.5(3) ?
O2 C7 C8 Cl2 . . . . -54.5(4) ?
C6 C1 C1' C6' . . . . -176.6(4) ?
C2 C1 C1' C6' . . . . 0.7(6) ?
C6 C1 C1' C2' . . . . 1.0(6) ?
C2 C1 C1' C2' . . . . 178.2(4) ?
C6' C1' C2' C3' . . . . 1.2(6) ?
C1 C1' C2' C3' . . . . -176.4(4) ?
C1' C2' C3' C4' . . . . -0.5(7) ?
C2' C3' C4' C5' . . . . -0.8(7) ?
C3' C4' C5' C6' . . . . 1.2(7) ?
C4' C5' C6' C1' . . . . -0.5(7) ?
C2' C1' C6' C5' . . . . -0.8(6) ?
C1 C1' C6' C5' . . . . 176.9(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744848
