##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Biphenyl-4-yl 2,2,2-trichloroethyl sulfate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 Cl3 O4 S'
_chemical_formula_sum     'C14 H11 Cl3 O4 S'
_chemical_formula_iupac     'C14 H11 Cl3 O4 S'
_chemical_formula_weight     381.64
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     7.5761(2)
_cell_length_b     5.8272(2)
_cell_length_c     35.2679(11)
_cell_angle_alpha     90.00
_cell_angle_beta     90.181(2)
_cell_angle_gamma     90.00
_cell_volume     1556.98(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     19102
_cell_measurement_theta_min     1.00
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     slab
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.628
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     776
_exptl_absorpt_coefficient_mu     0.736
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker Nonius, 2006)'
_exptl_absorpt_correction_T_min     0.699
_exptl_absorpt_correction_T_max     0.944
_exptl_special_details
;
;
_diffrn_ambient_temperature     90.0(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Nonius KappaCCD diffractometer'
_diffrn_measurement_method     '\w scans at fixed \c = 55\%'
_diffrn_detector_area_resol_mean     18
_diffrn_reflns_number     15429
_diffrn_reflns_av_R_equivalents     0.0787
_diffrn_reflns_av_sigmaI/netI     0.0697
_diffrn_reflns_theta_min     2.31
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -43
_diffrn_reflns_limit_l_max     43
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
wR and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
2\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. <i>R</i>-factors
based on <i>F</i>^2^ are statistically about twice as large as those based on
<i>F</i>, and <i>R</i>- factors based on ALL data will be even larger.
;
_reflns_number_total     3041
_reflns_number_gt     1939
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1028
_refine_ls_R_factor_gt     0.0538
_refine_ls_wR_factor_gt     0.1154
_refine_ls_wR_factor_ref     0.1370
_refine_ls_goodness_of_fit_ref     1.091
_refine_ls_restrained_S_all     1.091
_refine_ls_number_reflns     3041
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[\s^2^(Fo^2^)+(0.0617P)^2^+1.4460P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.620
_refine_diff_density_min     -0.460
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELX97 (Sheldrick, 2008) and local procedures
;
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_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0235(6) 0.0200(6) 0.0188(5) 0.0022(5) -0.0014(4) 0.0011(4)
    O1 0.0250(16) 0.0222(17) 0.0187(14) 0.0051(13) -0.0025(12) 0.0031(12)
    O2 0.0179(15) 0.0206(16) 0.0242(15) 0.0040(13) -0.0021(11) -0.0042(12)
    O3 0.0283(16) 0.0268(18) 0.0232(14) 0.0012(14) 0.0034(12) 0.0018(13)
    O4 0.0368(17) 0.0170(16) 0.0245(15) 0.0058(14) -0.0058(13) -0.0071(13)
    Cl1 0.0364(6) 0.0211(6) 0.0267(5) -0.0025(5) -0.0040(5) -0.0021(4)
    Cl2 0.0223(6) 0.0371(7) 0.0274(6) 0.0027(5) 0.0009(4) -0.0017(5)
    Cl3 0.0353(6) 0.0243(6) 0.0186(5) -0.0011(5) 0.0026(4) 0.0022(4)
    C1 0.014(2) 0.021(2) 0.023(2) 0.0037(18) -0.0018(16) 0.0023(18)
    C2 0.032(2) 0.011(2) 0.027(2) -0.0016(19) -0.0028(18) 0.0027(18)
    C3 0.038(3) 0.018(2) 0.019(2) -0.004(2) -0.0042(19) 0.0019(18)
    C4 0.018(2) 0.022(2) 0.0171(19) 0.0096(18) -0.0041(16) -0.0004(18)
    C5 0.024(2) 0.029(3) 0.026(2) -0.009(2) -0.0031(18) 0.0021(19)
    C6 0.022(2) 0.026(3) 0.024(2) -0.0067(19) -0.0041(17) -0.0071(19)
    C7 0.028(2) 0.015(2) 0.0177(19) 0.0027(18) -0.0002(17) -0.0003(16)
    C8 0.024(2) 0.016(2) 0.021(2) 0.0034(18) 0.0002(17) -0.0008(17)
    C1' 0.016(2) 0.018(2) 0.022(2) -0.0012(18) -0.0009(16) -0.0024(17)
    C2' 0.034(3) 0.022(3) 0.024(2) -0.003(2) 0.0029(19) 0.0009(19)
    C3' 0.037(3) 0.030(3) 0.024(2) -0.004(2) 0.005(2) -0.006(2)
    C4' 0.026(2) 0.034(3) 0.019(2) 0.005(2) 0.0074(18) -0.0019(19)
    C5' 0.043(3) 0.030(3) 0.026(2) -0.013(2) 0.012(2) -0.001(2)
    C6' 0.031(3) 0.031(3) 0.030(2) -0.009(2) 0.006(2) -0.008(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell esds are taken into
account individually in the estimation of esds in distances, angles and
torsion angles; correlations between esds in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) ?
data_global
_journal_date_recd_electronic     2010-03-19
_journal_date_accepted     2010-04-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      5
_journal_page_first     o1073
_journal_page_last     o1073
_journal_paper_category     QO
_journal_coeditor_code     OM2330
_publ_contact_author_name     'Hans-Joachim Lehmler'
_publ_contact_author_address
;
Department of Occupational and Environmental Health
University of Iowa
100 Oakdale Campus, 124 IREH
Iowa City
IA 52242-5000
USA
;
_publ_contact_author_email     hans-joachim-lehmler@uiowa.edu
_publ_contact_author_fax     '1 (319) 335-4290'
_publ_contact_author_phone     '1 (319) 335-4211'
_publ_section_title
;
Biphenyl-4-yl 2,2,2-trichloroethyl sulfate
;
loop_
    _publ_author_name
    _publ_author_address
    'Li, Xueshu'
;
Department of Occupational and Environmental Health
University of Iowa
100 Oakdale Campus, 124 IREH
Iowa City
IA 52242-5000
USA
;
    'Parkin, Sean'
;
Department of Chemistry
University of Kentucky
Lexington
KY 40506-0055
USA
;
    'Duffel, Michael W.'
;
College of Pharmacy
Division of Medicinal and Natural Products Chemistry
University of Iowa
Iowa City
IA 52242
USA
;
    'Robertson, Larry W.'
;
Department of Occupational and Environmental Health
University of Iowa
100 Oakdale Campus, 124 IREH
Iowa City
IA 52242-5000
USA
;
    'Lehmler, Hans-Joachim'
;
Department of Occupational and Environmental Health
University of Iowa
100 Oakdale Campus, 124 IREH
Iowa City
IA 52242-5000
USA
;