############################################################################## ### ### ### 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. # # # ############################################################################## 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 ;