##############################################################################
### ###
### 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 #
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# This file may be used for bona fide research purposes within the #
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data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
4'-Chlorobiphenyl-3-yl 2,2,2-trichloroethyl sulfate
;
_chemical_name_common ?
_chemical_formula_moiety 'C14 H10 Cl4 O4 S'
_chemical_formula_sum 'C14 H10 Cl4 O4 S'
_chemical_formula_iupac 'C14 H10 Cl4 O4 S'
_chemical_formula_weight 416.08
_chemical_melting_point ?
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_H-M 'I 2/a'
_symmetry_space_group_name_Hall '-I 2ya'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
_cell_length_a 21.1900(3)
_cell_length_b 5.85430(10)
_cell_length_c 26.6803(5)
_cell_angle_alpha 90.00
_cell_angle_beta 98.3040(10)
_cell_angle_gamma 90.00
_cell_volume 3275.06(10)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 4127
_cell_measurement_theta_min 1.00
_cell_measurement_theta_max 27.48
_cell_measurement_temperature 90.0(2)
_exptl_crystal_description plate
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.41
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.06
_exptl_crystal_density_diffrn 1.688
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1680
_exptl_absorpt_coefficient_mu 0.865
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.718
_exptl_absorpt_correction_T_max 0.950
_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 30021
_diffrn_reflns_av_R_equivalents 0.0410
_diffrn_reflns_av_sigmaI/netI 0.0274
_diffrn_reflns_theta_min 1.54
_diffrn_reflns_theta_max 27.49
_diffrn_reflns_theta_full 27.49
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min -27
_diffrn_reflns_limit_h_max 27
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_limit_l_max 34
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
2\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total 3759
_reflns_number_gt 3242
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0330
_refine_ls_R_factor_gt 0.0257
_refine_ls_wR_factor_gt 0.0641
_refine_ls_wR_factor_ref 0.0672
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_restrained_S_all 1.049
_refine_ls_number_reflns 3759
_refine_ls_number_parameters 208
_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^)+(0.0294P)^2^+3.9224P] 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 0.386
_refine_diff_density_min -0.383
_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
;
SHELXL97 (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 0.205499(17) 0.54226(7) 0.300571(14) 0.01597(9) Uani d . 1 . .
O O1 0.18726(5) 0.4208(2) 0.24808(4) 0.0172(2) Uani d . 1 . .
O O2 0.19895(5) 0.3440(2) 0.33919(4) 0.0183(2) Uani d . 1 . .
O O3 0.15849(5) 0.7045(2) 0.30865(4) 0.0221(2) Uani d . 1 . .
O O4 0.27060(5) 0.6040(2) 0.30274(4) 0.0248(3) Uani d . 1 . .
Cl Cl1 -0.064775(19) 1.32997(7) 0.026719(15) 0.02388(10) Uani d . 1 . .
Cl Cl2 0.279773(19) 0.45519(7) 0.437358(15) 0.02180(10) Uani d . 1 . .
Cl Cl3 0.333188(17) 0.00690(7) 0.427046(15) 0.02125(10) Uani d . 1 . .
Cl Cl4 0.199083(17) 0.05436(7) 0.434813(14) 0.01980(10) Uani d . 1 . .
C C1 0.01131(7) 0.7573(3) 0.13260(5) 0.0141(3) Uani d . 1 . .
C C2 -0.05371(7) 0.8102(3) 0.12421(6) 0.0169(3) Uani d . 1 . .
H H2 -0.0823 0.7255 0.1414 0.020 Uiso calc R 1 . .
C C3 -0.07744(7) 0.9834(3) 0.09145(6) 0.0182(3) Uani d . 1 . .
H H3 -0.1217 1.0176 0.0863 0.022 Uiso calc R 1 . .
C C4 -0.03566(7) 1.1058(3) 0.06635(6) 0.0173(3) Uani d . 1 . .
C C5 0.02901(7) 1.0572(3) 0.07324(6) 0.0179(3) Uani d . 1 . .
H H5 0.0571 1.1412 0.0555 0.021 Uiso calc R 1 . .
C C6 0.05201(7) 0.8843(3) 0.10634(6) 0.0169(3) Uani d . 1 . .
H H6 0.0964 0.8512 0.1114 0.020 Uiso calc R 1 . .
C C1' 0.03627(7) 0.5740(3) 0.16854(5) 0.0139(3) Uani d . 1 . .
C C2' 0.09909(7) 0.5839(3) 0.19354(5) 0.0147(3) Uani d . 1 . .
H H2' 0.1259 0.7090 0.1881 0.018 Uiso calc R 1 . .
C C3' 0.12148(7) 0.4097(3) 0.22605(5) 0.0150(3) Uani d . 1 . .
C C4' 0.08533(7) 0.2238(3) 0.23630(6) 0.0169(3) Uani d . 1 . .
H H4' 0.1025 0.1062 0.2588 0.020 Uiso calc R 1 . .
C C5' 0.02240(7) 0.2170(3) 0.21209(6) 0.0175(3) Uani d . 1 . .
H H5' -0.0044 0.0935 0.2186 0.021 Uiso calc R 1 . .
C C6' -0.00152(7) 0.3877(3) 0.17880(5) 0.0155(3) Uani d . 1 . .
H H6' -0.0444 0.3785 0.1625 0.019 Uiso calc R 1 . .
C C7 0.25272(7) 0.1927(3) 0.35354(6) 0.0166(3) Uani d . 1 . .
H H7A 0.2910 0.2522 0.3406 0.020 Uiso calc R 1 . .
H H7B 0.2431 0.0387 0.3391 0.020 Uiso calc R 1 . .
C C8 0.26470(7) 0.1800(3) 0.41106(6) 0.0153(3) Uani d . 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 0.01324(17) 0.0176(2) 0.01656(19) -0.00114(14) 0.00035(13) 0.00386(14)
O1 0.0119(5) 0.0242(6) 0.0157(5) 0.0030(4) 0.0023(4) 0.0016(5)
O2 0.0130(5) 0.0241(6) 0.0179(5) 0.0007(4) 0.0025(4) 0.0087(5)
O3 0.0221(6) 0.0204(6) 0.0228(6) 0.0036(5) 0.0000(4) -0.0015(5)
O4 0.0158(5) 0.0291(7) 0.0282(6) -0.0073(5) -0.0011(4) 0.0095(5)
Cl1 0.0251(2) 0.0248(2) 0.0220(2) 0.00861(17) 0.00412(15) 0.00689(16)
Cl2 0.0263(2) 0.0171(2) 0.0219(2) -0.00104(15) 0.00333(15) -0.00356(15)
Cl3 0.01544(17) 0.0210(2) 0.0267(2) 0.00532(15) 0.00114(14) 0.00543(16)
Cl4 0.01582(17) 0.0237(2) 0.02059(19) -0.00115(15) 0.00512(14) 0.00656(15)
C1 0.0139(7) 0.0161(7) 0.0124(7) -0.0002(6) 0.0017(5) -0.0024(6)
C2 0.0122(7) 0.0210(8) 0.0178(7) -0.0024(6) 0.0032(5) -0.0008(6)
C3 0.0115(7) 0.0231(8) 0.0196(8) 0.0011(6) 0.0003(6) -0.0021(6)
C4 0.0196(7) 0.0177(8) 0.0137(7) 0.0047(6) 0.0000(6) 0.0007(6)
C5 0.0179(7) 0.0195(8) 0.0175(8) -0.0004(6) 0.0066(6) 0.0017(6)
C6 0.0120(7) 0.0203(8) 0.0190(7) 0.0020(6) 0.0048(5) -0.0003(6)
C1' 0.0127(6) 0.0173(8) 0.0123(7) 0.0005(6) 0.0034(5) -0.0017(6)
C2' 0.0132(7) 0.0170(8) 0.0149(7) -0.0011(6) 0.0050(5) -0.0005(6)
C3' 0.0109(6) 0.0199(8) 0.0144(7) 0.0023(6) 0.0027(5) -0.0021(6)
C4' 0.0213(7) 0.0158(8) 0.0143(7) 0.0018(6) 0.0051(6) 0.0006(6)
C5' 0.0215(8) 0.0166(8) 0.0155(7) -0.0053(6) 0.0067(6) -0.0028(6)
C6' 0.0145(7) 0.0186(8) 0.0138(7) -0.0019(6) 0.0034(5) -0.0033(6)
C7 0.0168(7) 0.0180(8) 0.0152(7) 0.0029(6) 0.0030(5) 0.0024(6)
C8 0.0136(7) 0.0145(7) 0.0180(7) 0.0016(6) 0.0031(5) 0.0009(6)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 . 1.4153(12) ?
S1 O4 . 1.4191(11) ?
S1 O1 . 1.5685(11) ?
S1 O2 . 1.5714(11) ?
O1 C3' . 1.4338(17) ?
O2 C7 . 1.4503(18) ?
Cl1 C4 . 1.7412(16) ?
Cl2 C8 . 1.7677(16) ?
Cl3 C8 . 1.7710(15) ?
Cl4 C8 . 1.7693(15) ?
C1 C2 . 1.398(2) ?
C1 C6 . 1.401(2) ?
C1 C1' . 1.485(2) ?
C2 C3 . 1.385(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.385(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.386(2) ?
C5 C6 . 1.385(2) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C1' C2' . 1.401(2) ?
C1' C6' . 1.403(2) ?
C2' C3' . 1.378(2) ?
C2' H2' . 0.9500 ?
C3' C4' . 1.381(2) ?
C4' C5' . 1.396(2) ?
C4' H4' . 0.9500 ?
C5' C6' . 1.384(2) ?
C5' H5' . 0.9500 ?
C6' H6' . 0.9500 ?
C7 C8 . 1.521(2) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
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 . . 121.62(8) ?
O3 S1 O1 . . 110.62(6) ?
O4 S1 O1 . . 105.34(7) ?
O3 S1 O2 . . 105.39(7) ?
O4 S1 O2 . . 109.79(6) ?
O1 S1 O2 . . 102.53(6) ?
C3' O1 S1 . . 119.08(9) ?
C7 O2 S1 . . 118.95(9) ?
C2 C1 C6 . . 117.78(14) ?
C2 C1 C1' . . 120.96(13) ?
C6 C1 C1' . . 121.26(13) ?
C3 C2 C1 . . 121.53(14) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
C2 C3 C4 . . 119.01(14) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C3 C4 C5 . . 121.24(15) ?
C3 C4 Cl1 . . 119.25(12) ?
C5 C4 Cl1 . . 119.48(12) ?
C6 C5 C4 . . 119.01(14) ?
C6 C5 H5 . . 120.5 ?
C4 C5 H5 . . 120.5 ?
C5 C6 C1 . . 121.43(14) ?
C5 C6 H6 . . 119.3 ?
C1 C6 H6 . . 119.3 ?
C2' C1' C6' . . 117.97(14) ?
C2' C1' C1 . . 120.18(13) ?
C6' C1' C1 . . 121.85(13) ?
C3' C2' C1' . . 119.08(14) ?
C3' C2' H2' . . 120.5 ?
C1' C2' H2' . . 120.5 ?
C2' C3' C4' . . 123.88(14) ?
C2' C3' O1 . . 116.77(13) ?
C4' C3' O1 . . 119.27(14) ?
C3' C4' C5' . . 116.82(14) ?
C3' C4' H4' . . 121.6 ?
C5' C4' H4' . . 121.6 ?
C6' C5' C4' . . 120.90(14) ?
C6' C5' H5' . . 119.6 ?
C4' C5' H5' . . 119.6 ?
C5' C6' C1' . . 121.33(14) ?
C5' C6' H6' . . 119.3 ?
C1' C6' H6' . . 119.3 ?
O2 C7 C8 . . 107.85(12) ?
O2 C7 H7A . . 110.1 ?
C8 C7 H7A . . 110.1 ?
O2 C7 H7B . . 110.1 ?
C8 C7 H7B . . 110.1 ?
H7A C7 H7B . . 108.5 ?
C7 C8 Cl2 . . 110.51(11) ?
C7 C8 Cl4 . . 110.88(11) ?
Cl2 C8 Cl4 . . 110.07(8) ?
C7 C8 Cl3 . . 106.40(10) ?
Cl2 C8 Cl3 . . 109.34(8) ?
Cl4 C8 Cl3 . . 109.56(8) ?
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 C3' . . . . -24.84(13) ?
O4 S1 O1 C3' . . . . -158.01(11) ?
O2 S1 O1 C3' . . . . 87.12(11) ?
O3 S1 O2 C7 . . . . -158.44(11) ?
O4 S1 O2 C7 . . . . -25.84(13) ?
O1 S1 O2 C7 . . . . 85.75(11) ?
C6 C1 C2 C3 . . . . -0.5(2) ?
C1' C1 C2 C3 . . . . 178.90(14) ?
C1 C2 C3 C4 . . . . 0.2(2) ?
C2 C3 C4 C5 . . . . 0.4(2) ?
C2 C3 C4 Cl1 . . . . -177.88(12) ?
C3 C4 C5 C6 . . . . -0.7(2) ?
Cl1 C4 C5 C6 . . . . 177.54(12) ?
C4 C5 C6 C1 . . . . 0.4(2) ?
C2 C1 C6 C5 . . . . 0.2(2) ?
C1' C1 C6 C5 . . . . -179.25(14) ?
C2 C1 C1' C2' . . . . -152.01(15) ?
C6 C1 C1' C2' . . . . 27.4(2) ?
C2 C1 C1' C6' . . . . 27.7(2) ?
C6 C1 C1' C6' . . . . -152.88(15) ?
C6' C1' C2' C3' . . . . 1.4(2) ?
C1 C1' C2' C3' . . . . -178.90(13) ?
C1' C2' C3' C4' . . . . -0.8(2) ?
C1' C2' C3' O1 . . . . 176.06(13) ?
S1 O1 C3' C2' . . . . 91.88(14) ?
S1 O1 C3' C4' . . . . -91.13(15) ?
C2' C3' C4' C5' . . . . -0.5(2) ?
O1 C3' C4' C5' . . . . -177.25(13) ?
C3' C4' C5' C6' . . . . 1.2(2) ?
C4' C5' C6' C1' . . . . -0.6(2) ?
C2' C1' C6' C5' . . . . -0.7(2) ?
C1 C1' C6' C5' . . . . 179.55(14) ?
S1 O2 C7 C8 . . . . 129.66(11) ?
O2 C7 C8 Cl2 . . . . -58.24(14) ?
O2 C7 C8 Cl4 . . . . 64.09(14) ?
O2 C7 C8 Cl3 . . . . -176.84(10) ?
data_global
_journal_date_recd_electronic 2010-07-21
_journal_date_accepted 2010-08-04
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2010
_journal_volume 66
_journal_issue 9
_journal_page_first o2306
_journal_page_last o2306
_journal_paper_category QO
_journal_coeditor_code OM2350
_publ_contact_author_name 'Hans-Joachim Lehmler'
_publ_contact_author_address
;
The University of Iowa
Department of Occupational and Environmental Health
100 Oakdale Campus, 124 IREH
Iowa City, IA 52242-5000
USA
;
_publ_contact_author_email 'hans-joachim-lehmler@uiowa.edu'
_publ_contact_author_fax ?
_publ_contact_author_phone ?
_publ_section_title
;
4'-Chlorobiphenyl-3-yl 2,2,2-trichloroethyl sulfate
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Li, Xueshu' .
;
The University of Iowa
Department of Occupational and Environmental Health
UI Research Campus, 124 IREH
Iowa City, IA 52242-5000
USA
;
'Parkin, Sean' .
;
University of Kentucky
Department of Chemistry
Lexington, KY 40506-0055
USA
;
'Duffel, Michael W.' .
;
Division of Medicinal and Natural Products Chemistry, College of Pharmacy,
University of Iowa, Iowa City, IA 52242, USA
;
'Robertson, Larry W.' .
;
The University of Iowa
Department of Occupational and Environmental Health
UI Research Campus, 124 IREH
Iowa City, IA 52242-5000
USA
;
'Lehmler, Hans-Joachim' .
;
The University of Iowa
Department of Occupational and Environmental Health
UI Research Campus, 124 IREH
Iowa City, IA 52242-5000
USA
;