# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_xc_viii_104_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N O'
_chemical_formula_sum            'C14 H19 N O'
_chemical_formula_weight         217.30
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   7.0592(2)
_cell_length_b                   9.6718(3)
_cell_length_c                   18.5618(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.179(2)
_cell_angle_gamma                90.00
_cell_volume                     1267.04(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    228(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8976
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      228(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6867
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.77
_diffrn_reflns_theta_max         65.96
_reflns_number_total             1913
_reflns_number_gt                1809
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008); OLEX2'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 (Bruker, 2010)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0696P)²+0.0917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(3)
_refine_ls_number_reflns         1913
_refine_ls_number_parameters     156
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.2539(3) 0.68310(19) -0.04139(9) 0.0411(4) Uani 1 1 d . . .
C2 C -0.2536(2) 0.7923(2) 0.00175(9) 0.0316(4) Uani 1 1 d . . .
C3 C -0.2621(2) 0.7599(2) 0.07987(9) 0.0346(4) Uani 1 1 d . . .
H3 H -0.2780 0.6614 0.0929 0.042 Uiso 1 1 calc R . .
C4 C -0.1395(3) 0.8474(2) 0.13096(9) 0.0338(4) Uani 1 1 d . . .
H4 H -0.0679 0.9227 0.1077 0.041 Uiso 1 1 calc R . .
C5 C -0.0404(2) 0.77922(19) 0.19268(8) 0.0317(4) Uani 1 1 d . . .
C6 C -0.1255(3) 0.6784(2) 0.23456(10) 0.0418(5) Uani 1 1 d . . .
H6 H -0.2509 0.6518 0.2238 0.050 Uiso 1 1 calc R . .
C7 C -0.0298(3) 0.6165(2) 0.29165(10) 0.0415(5) Uani 1 1 d . . .
H7 H -0.0921 0.5490 0.3188 0.050 Uiso 1 1 calc R . .
C8 C 0.1561(3) 0.65115(19) 0.31010(9) 0.0339(4) Uani 1 1 d . . .
C9 C 0.2588(3) 0.5885(2) 0.37591(10) 0.0418(5) Uani 1 1 d . . .
C10 C 0.4683(4) 0.5646(3) 0.36158(13) 0.0603(7) Uani 1 1 d . . .
H10A H 0.4808 0.5022 0.3210 0.090 Uiso 1 1 calc R . .
H10B H 0.5290 0.5242 0.4039 0.090 Uiso 1 1 calc R . .
H10C H 0.5283 0.6521 0.3507 0.090 Uiso 1 1 calc R . .
C11 C 0.1722(5) 0.4523(4) 0.3984(2) 0.0967(13) Uani 1 1 d . . .
H11A H 0.1779 0.3871 0.3588 0.145 Uiso 1 1 calc R . .
H11B H 0.0411 0.4669 0.4111 0.145 Uiso 1 1 calc R . .
H11C H 0.2420 0.4158 0.4397 0.145 Uiso 1 1 calc R . .
C12 C -0.3508(3) 0.8640(2) 0.12864(10) 0.0423(5) Uani 1 1 d . . .
H12A H -0.4216 0.8290 0.1697 0.051 Uiso 1 1 calc R . .
H12B H -0.4027 0.9483 0.1066 0.051 Uiso 1 1 calc R . .
C13 C 0.1449(3) 0.8141(2) 0.21083(10) 0.0349(4) Uani 1 1 d . . .
H13 H 0.2071 0.8818 0.1837 0.042 Uiso 1 1 calc R . .
C14 C 0.2405(3) 0.7516(2) 0.26791(10) 0.0370(4) Uani 1 1 d . . .
H14 H 0.3662 0.7778 0.2785 0.044 Uiso 1 1 calc R . .
C15 C 0.2457(4) 0.6942(3) 0.43782(12) 0.0635(7) Uani 1 1 d . . .
H15A H 0.3091 0.6576 0.4806 0.095 Uiso 1 1 calc R . .
H15B H 0.1136 0.7116 0.4480 0.095 Uiso 1 1 calc R . .
H15C H 0.3061 0.7799 0.4238 0.095 Uiso 1 1 calc R . .
O1 O -0.2465(2) 0.91199(14) -0.02137(7) 0.0408(3) Uani 1 1 d . . .
H1A H -0.243(3) 0.696(3) -0.0859(15) 0.044(6) Uiso 1 1 d . . .
H1B H -0.252(3) 0.599(3) -0.0242(13) 0.043(6) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0617(11) 0.0310(11) 0.0306(9) 0.0027(7) -0.0029(7) -0.0011(8)
C2 0.0305(7) 0.0305(10) 0.0337(8) 0.0014(7) -0.0023(6) -0.0022(7)
C3 0.0338(8) 0.0357(11) 0.0343(9) 0.0028(8) -0.0021(6) -0.0031(7)
C4 0.0364(9) 0.0348(10) 0.0301(8) -0.0006(7) 0.0021(7) -0.0030(7)
C5 0.0355(8) 0.0330(10) 0.0268(8) -0.0039(7) 0.0040(6) -0.0048(7)
C6 0.0336(9) 0.0513(13) 0.0402(10) 0.0067(9) -0.0031(7) -0.0125(8)
C7 0.0415(10) 0.0460(12) 0.0370(10) 0.0094(8) 0.0007(7) -0.0123(9)
C8 0.0379(9) 0.0335(11) 0.0302(9) -0.0022(7) 0.0018(7) -0.0052(7)
C9 0.0462(10) 0.0447(12) 0.0342(9) 0.0048(8) -0.0046(7) -0.0067(8)
C10 0.0568(13) 0.0695(18) 0.0543(13) 0.0056(11) -0.0030(10) 0.0159(11)
C11 0.101(2) 0.078(2) 0.109(3) 0.057(2) -0.0487(19) -0.0382(18)
C12 0.0369(10) 0.0543(13) 0.0359(10) 0.0028(8) 0.0055(7) 0.0043(8)
C13 0.0401(9) 0.0341(11) 0.0308(8) -0.0002(7) 0.0039(7) -0.0110(7)
C14 0.0343(8) 0.0423(12) 0.0342(9) -0.0016(8) -0.0030(7) -0.0108(8)
C15 0.0671(15) 0.089(2) 0.0341(10) -0.0044(12) -0.0056(9) 0.0132(13)
O1 0.0544(8) 0.0323(8) 0.0356(7) 0.0025(6) -0.0023(5) 0.0006(6)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.325(3) . ?
N1 H1A 0.84(3) . ?
N1 H1B 0.88(3) . ?
C2 O1 1.236(2) . ?
C2 C3 1.486(3) . ?
C3 C12 1.499(3) . ?
C3 C4 1.527(2) . ?
C3 H3 0.9900 . ?
C4 C5 1.485(2) . ?
C4 C12 1.499(3) . ?
C4 H4 0.9900 . ?
C5 C13 1.386(3) . ?
C5 C6 1.391(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9400 . ?
C8 C14 1.389(3) . ?
C8 C9 1.533(3) . ?
C9 C11 1.514(4) . ?
C9 C10 1.525(3) . ?
C9 C15 1.543(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9400 . ?
C14 H14 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1A 118.5(17) . . ?
C2 N1 H1B 121.4(15) . . ?
H1A N1 H1B 120(2) . . ?
O1 C2 N1 122.42(17) . . ?
O1 C2 C3 122.63(17) . . ?
N1 C2 C3 114.95(17) . . ?
C2 C3 C12 118.24(16) . . ?
C2 C3 C4 117.08(16) . . ?
C12 C3 C4 59.40(12) . . ?
C2 C3 H3 116.6 . . ?
C12 C3 H3 116.6 . . ?
C4 C3 H3 116.6 . . ?
C5 C4 C12 121.48(16) . . ?
C5 C4 C3 119.01(16) . . ?
C12 C4 C3 59.39(13) . . ?
C5 C4 H4 115.2 . . ?
C12 C4 H4 115.2 . . ?
C3 C4 H4 115.2 . . ?
C13 C5 C6 116.81(16) . . ?
C13 C5 C4 120.47(16) . . ?
C6 C5 C4 122.72(16) . . ?
C7 C6 C5 121.50(17) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 121.91(17) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C14 C8 C7 116.29(17) . . ?
C14 C8 C9 121.63(16) . . ?
C7 C8 C9 121.99(16) . . ?
C11 C9 C10 108.4(2) . . ?
C11 C9 C8 112.11(18) . . ?
C10 C9 C8 111.44(16) . . ?
C11 C9 C15 109.9(2) . . ?
C10 C9 C15 107.68(19) . . ?
C8 C9 C15 107.27(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 C4 61.21(12) . . ?
C3 C12 H12A 117.6 . . ?
C4 C12 H12A 117.6 . . ?
C3 C12 H12B 117.6 . . ?
C4 C12 H12B 117.6 . . ?
H12A C12 H12B 114.8 . . ?
C14 C13 C5 121.53(17) . . ?
C14 C13 H13 119.2 . . ?
C5 C13 H13 119.2 . . ?
C13 C14 C8 121.96(16) . . ?
C13 C14 H14 119.0 . . ?
C8 C14 H14 119.0 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C12 28.2(2) . . . . ?
N1 C2 C3 C12 -151.94(17) . . . . ?
O1 C2 C3 C4 -39.8(2) . . . . ?
N1 C2 C3 C4 140.04(18) . . . . ?
C2 C3 C4 C5 -140.19(17) . . . . ?
C12 C3 C4 C5 111.45(19) . . . . ?
C2 C3 C4 C12 108.36(19) . . . . ?
C12 C4 C5 C13 -152.07(19) . . . . ?
C3 C4 C5 C13 138.00(18) . . . . ?
C12 C4 C5 C6 28.3(3) . . . . ?
C3 C4 C5 C6 -41.7(3) . . . . ?
C13 C5 C6 C7 0.2(3) . . . . ?
C4 C5 C6 C7 179.91(19) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C14 0.0(3) . . . . ?
C6 C7 C8 C9 176.6(2) . . . . ?
C14 C8 C9 C11 -161.1(3) . . . . ?
C7 C8 C9 C11 22.5(3) . . . . ?
C14 C8 C9 C10 -39.4(3) . . . . ?
C7 C8 C9 C10 144.2(2) . . . . ?
C14 C8 C9 C15 78.2(2) . . . . ?
C7 C8 C9 C15 -98.2(2) . . . . ?
C2 C3 C12 C4 -106.43(18) . . . . ?
C5 C4 C12 C3 -107.4(2) . . . . ?
C6 C5 C13 C14 0.0(3) . . . . ?
C4 C5 C13 C14 -179.73(17) . . . . ?
C5 C13 C14 C8 -0.2(3) . . . . ?
C7 C8 C14 C13 0.2(3) . . . . ?
C9 C8 C14 C13 -176.38(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        65.96
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.033
_database_code_depnum_ccdc_archive 'CCDC 1020629'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_xc_vii_129_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 O4 S'
_chemical_formula_sum            'C12 H14 O4 S'
_chemical_formula_weight         254.29
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.70370(10)
_cell_length_b                   10.0938(2)
_cell_length_c                   9.5452(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.1320(10)
_cell_angle_gamma                90.00
_cell_volume                     613.81(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    2.370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_T_max  0.6486
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6686
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.87
_diffrn_reflns_theta_max         68.16
_reflns_number_total             2144
_reflns_number_gt                2033
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008); OLEX2 (2009)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 (Bruker, 2010)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0449P)²+0.0153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0073(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(19)
_refine_ls_number_reflns         2144
_refine_ls_number_parameters     156
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.11517(7) 0.60986(5) 0.43726(6) 0.03182(16) Uani 1 1 d . . .
O1 O 0.4858(3) 0.47378(16) 0.32220(18) 0.0349(4) Uani 1 1 d . . .
O2 O 0.3061(3) 0.30364(18) 0.3733(2) 0.0418(4) Uani 1 1 d . . .
O3 O 0.1791(3) 0.74480(18) 0.4717(2) 0.0487(5) Uani 1 1 d . . .
O4 O 0.0078(3) 0.5758(2) 0.2872(2) 0.0520(5) Uani 1 1 d . . .
C1 C 0.5220(5) 0.3983(3) 0.2038(3) 0.0469(7) Uani 1 1 d . . .
H1A H 0.5920 0.3159 0.2425 0.070 Uiso 1 1 calc R . .
H1B H 0.6094 0.4492 0.1595 0.070 Uiso 1 1 calc R . .
H1C H 0.3887 0.3792 0.1299 0.070 Uiso 1 1 calc R . .
C2 C 0.3750(3) 0.4142(2) 0.3973(2) 0.0272(4) Uani 1 1 d . . .
C3 C 0.3462(3) 0.5051(2) 0.5149(2) 0.0269(4) Uani 1 1 d . . .
H3 H 0.4720 0.5619 0.5525 0.032 Uiso 1 1 calc R . .
C4 C 0.3054(3) 0.4322(2) 0.6449(2) 0.0276(4) Uani 1 1 d . . .
H4 H 0.2352 0.3475 0.6066 0.033 Uiso 1 1 calc R . .
C5 C 0.5037(3) 0.3991(2) 0.7690(2) 0.0299(5) Uani 1 1 d . . .
C6 C 0.5350(4) 0.2711(3) 0.8217(3) 0.0445(6) Uani 1 1 d . . .
H6 H 0.4359 0.2052 0.7785 0.053 Uiso 1 1 calc R . .
C7 C 0.7132(5) 0.2389(3) 0.9387(3) 0.0567(8) Uani 1 1 d . . .
H7 H 0.7341 0.1511 0.9730 0.068 Uiso 1 1 calc R . .
C8 C 0.8565(4) 0.3334(4) 1.0035(3) 0.0559(9) Uani 1 1 d . . .
H8 H 0.9756 0.3113 1.0828 0.067 Uiso 1 1 calc R . .
C9 C -0.0236(3) 0.5551(3) 0.5580(3) 0.0368(5) Uani 1 1 d . . .
H9A H -0.1100 0.6265 0.5782 0.044 Uiso 1 1 calc R . .
H9B H -0.1139 0.4793 0.5162 0.044 Uiso 1 1 calc R . .
C10 C 0.1486(3) 0.5160(2) 0.6961(3) 0.0351(5) Uani 1 1 d . . .
H10A H 0.0911 0.4642 0.7615 0.042 Uiso 1 1 calc R . .
H10B H 0.2178 0.5949 0.7494 0.042 Uiso 1 1 calc R . .
C11 C 0.6508(4) 0.4950(3) 0.8357(3) 0.0426(6) Uani 1 1 d . . .
H11 H 0.6314 0.5829 0.8016 0.051 Uiso 1 1 calc R . .
C12 C 0.8260(4) 0.4618(4) 0.9523(3) 0.0540(8) Uani 1 1 d . . .
H12 H 0.9250 0.5274 0.9968 0.065 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0308(2) 0.0297(3) 0.0338(3) 0.0009(2) 0.00834(17) 0.0054(2)
O1 0.0422(9) 0.0322(8) 0.0379(9) 0.0027(7) 0.0235(7) -0.0002(7)
O2 0.0518(10) 0.0345(9) 0.0479(10) -0.0105(7) 0.0282(8) -0.0108(8)
O3 0.0515(11) 0.0287(8) 0.0693(13) 0.0030(8) 0.0238(9) 0.0047(8)
O4 0.0415(9) 0.0707(15) 0.0360(9) -0.0006(8) 0.0009(7) 0.0143(9)
C1 0.0613(17) 0.0471(15) 0.0444(14) 0.0023(12) 0.0342(13) 0.0063(14)
C2 0.0242(9) 0.0281(10) 0.0300(10) 0.0009(9) 0.0097(7) 0.0002(9)
C3 0.0238(9) 0.0259(10) 0.0305(10) -0.0015(8) 0.0079(7) -0.0017(8)
C4 0.0263(10) 0.0287(10) 0.0282(10) -0.0020(8) 0.0089(8) -0.0029(8)
C5 0.0283(10) 0.0393(13) 0.0239(10) -0.0017(9) 0.0110(8) 0.0027(10)
C6 0.0486(14) 0.0405(14) 0.0370(13) -0.0032(11) 0.0023(10) 0.0097(12)
C7 0.0615(18) 0.0595(17) 0.0407(14) 0.0024(13) 0.0037(13) 0.0261(15)
C8 0.0352(14) 0.100(3) 0.0295(12) 0.0025(15) 0.0053(10) 0.0182(15)
C9 0.0279(10) 0.0371(11) 0.0481(14) -0.0016(10) 0.0159(9) 0.0026(10)
C10 0.0317(11) 0.0405(12) 0.0367(12) -0.0034(10) 0.0161(9) 0.0014(10)
C11 0.0375(12) 0.0564(16) 0.0327(12) 0.0010(11) 0.0092(9) -0.0132(12)
C12 0.0363(13) 0.095(2) 0.0303(12) -0.0068(15) 0.0104(10) -0.0191(15)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.4306(19) . ?
S1 O3 1.4350(19) . ?
S1 C9 1.780(3) . ?
S1 C3 1.831(2) . ?
O1 C2 1.327(3) . ?
O1 C1 1.444(3) . ?
O2 C2 1.202(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.507(3) . ?
C3 C4 1.538(3) . ?
C3 H3 0.9900 . ?
C4 C5 1.517(3) . ?
C4 C10 1.543(3) . ?
C4 H4 0.9900 . ?
C5 C6 1.379(4) . ?
C5 C11 1.387(4) . ?
C6 C7 1.397(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.358(5) . ?
C7 H7 0.9400 . ?
C8 C12 1.379(5) . ?
C8 H8 0.9400 . ?
C9 C10 1.510(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O3 118.62(13) . . ?
O4 S1 C9 111.89(12) . . ?
O3 S1 C9 108.96(12) . . ?
O4 S1 C3 111.41(11) . . ?
O3 S1 C3 107.52(11) . . ?
C9 S1 C3 96.05(10) . . ?
C2 O1 C1 116.26(19) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 124.3(2) . . ?
O2 C2 C3 125.20(19) . . ?
O1 C2 C3 110.47(18) . . ?
C2 C3 C4 113.95(18) . . ?
C2 C3 S1 109.77(14) . . ?
C4 C3 S1 105.21(14) . . ?
C2 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
S1 C3 H3 109.3 . . ?
C5 C4 C3 113.73(17) . . ?
C5 C4 C10 113.05(18) . . ?
C3 C4 C10 107.66(18) . . ?
C5 C4 H4 107.4 . . ?
C3 C4 H4 107.4 . . ?
C10 C4 H4 107.4 . . ?
C6 C5 C11 118.8(2) . . ?
C6 C5 C4 119.2(2) . . ?
C11 C5 C4 122.0(2) . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C12 119.5(2) . . ?
C7 C8 H8 120.2 . . ?
C12 C8 H8 120.2 . . ?
C10 C9 S1 103.59(15) . . ?
C10 C9 H9A 111.0 . . ?
S1 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
S1 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C9 C10 C4 106.14(18) . . ?
C9 C10 H10A 110.5 . . ?
C4 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
C4 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C12 C11 C5 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C5 C11 H11 119.9 . . ?
C8 C12 C11 120.5(3) . . ?
C8 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 O2 0.4(3) . . . . ?
C1 O1 C2 C3 -178.9(2) . . . . ?
O2 C2 C3 C4 24.9(3) . . . . ?
O1 C2 C3 C4 -155.79(17) . . . . ?
O2 C2 C3 S1 -92.8(2) . . . . ?
O1 C2 C3 S1 86.52(18) . . . . ?
O4 S1 C3 C2 3.89(19) . . . . ?
O3 S1 C3 C2 -127.65(16) . . . . ?
C9 S1 C3 C2 120.26(16) . . . . ?
O4 S1 C3 C4 -119.11(16) . . . . ?
O3 S1 C3 C4 109.35(16) . . . . ?
C9 S1 C3 C4 -2.74(16) . . . . ?
C2 C3 C4 C5 90.0(2) . . . . ?
S1 C3 C4 C5 -149.74(16) . . . . ?
C2 C3 C4 C10 -143.95(18) . . . . ?
S1 C3 C4 C10 -23.7(2) . . . . ?
C3 C4 C5 C6 -128.8(2) . . . . ?
C10 C4 C5 C6 108.0(2) . . . . ?
C3 C4 C5 C11 54.1(3) . . . . ?
C10 C4 C5 C11 -69.1(3) . . . . ?
C11 C5 C6 C7 -0.8(4) . . . . ?
C4 C5 C6 C7 -178.1(2) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C6 C7 C8 C12 -0.5(4) . . . . ?
O4 S1 C9 C10 144.43(16) . . . . ?
O3 S1 C9 C10 -82.43(18) . . . . ?
C3 S1 C9 C10 28.45(17) . . . . ?
S1 C9 C10 C4 -46.3(2) . . . . ?
C5 C4 C10 C9 172.62(19) . . . . ?
C3 C4 C10 C9 46.1(2) . . . . ?
C6 C5 C11 C12 0.4(4) . . . . ?
C4 C5 C11 C12 177.6(2) . . . . ?
C7 C8 C12 C11 0.1(4) . . . . ?
C5 C11 C12 C8 0.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        68.16
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 1020630'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_xc_viii_167_1_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 Cl2 F O4 S'
_chemical_formula_sum            'C12 H11 Cl2 F O4 S'
_chemical_formula_weight         341.17
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.7539(3)
_cell_length_b                   8.4364(3)
_cell_length_c                   22.2865(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1457.87(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    228(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    5.556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4895
_exptl_absorpt_correction_T_max  0.8970
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      228(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17397
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         68.23
_reflns_number_total             2634
_reflns_number_gt                2272
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'APEX2 (Bruker, 2010); SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009);XPREP(Sheldrick,2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008); OLEX2 (2009)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX2 (Bruker, 2010)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0227P)²+0.4814P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_number_reflns         2634
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.82735(15) 0.08278(16) 0.55851(4) 0.0737(4) Uani 1 1 d . . .
S1 S 0.86391(12) 0.30623(10) 0.23656(3) 0.0450(2) Uani 1 1 d . . .
Cl2 Cl 0.22493(16) -0.0585(2) 0.45310(6) 0.1030(6) Uani 1 1 d . . .
O1 O 1.0442(3) 0.3000(4) 0.22401(12) 0.0617(7) Uani 1 1 d . . .
O2 O 0.7677(4) 0.4400(4) 0.21693(11) 0.0681(8) Uani 1 1 d . . .
F3 F 0.9945(2) 0.2981(3) 0.34526(8) 0.0473(5) Uani 1 1 d . . .
O4 O 0.5652(3) 0.4175(3) 0.33264(11) 0.0524(6) Uani 1 1 d . . .
C1 C 0.5331(5) 0.0187(5) 0.49943(15) 0.0543(10) Uani 1 1 d . . .
H1 H 0.4852 -0.0053 0.5371 0.065 Uiso 1 1 calc R . .
C2 C 0.7012(5) 0.0681(5) 0.49391(15) 0.0506(9) Uani 1 1 d . . .
C3 C 0.7738(5) 0.1033(4) 0.43921(14) 0.0440(8) Uani 1 1 d . . .
H3 H 0.8894 0.1365 0.4369 0.053 Uiso 1 1 calc R . .
C4 C 0.6753(4) 0.0894(4) 0.38715(13) 0.0379(7) Uani 1 1 d . . .
C5 C 0.7585(4) 0.1190(4) 0.32706(14) 0.0387(7) Uani 1 1 d . . .
H5 H 0.8575 0.0452 0.3247 0.046 Uiso 1 1 calc R . .
C6 C 0.8340(4) 0.2852(4) 0.31983(13) 0.0383(7) Uani 1 1 d . . .
C7 C 0.7182(5) 0.4208(4) 0.34042(13) 0.0401(7) Uani 1 1 d . . .
O8 O 0.8081(4) 0.5350(3) 0.36545(11) 0.0530(6) Uani 1 1 d . . .
C9 C 0.4380(5) 0.0058(5) 0.44789(17) 0.0573(10) Uani 1 1 d . . .
C10 C 0.5040(5) 0.0420(5) 0.39214(15) 0.0490(9) Uani 1 1 d . . .
H10 H 0.4340 0.0347 0.3578 0.059 Uiso 1 1 calc R . .
C11 C 0.7583(5) 0.1267(5) 0.21669(16) 0.0517(10) Uani 1 1 d . . .
H11A H 0.6858 0.1417 0.1811 0.062 Uiso 1 1 calc R . .
H11B H 0.8424 0.0428 0.2085 0.062 Uiso 1 1 calc R . .
C12 C 0.6486(5) 0.0856(4) 0.27152(13) 0.0495(8) Uani 1 1 d . . .
H12A H 0.6149 -0.0263 0.2704 0.059 Uiso 1 1 calc R . .
H12B H 0.5438 0.1506 0.2722 0.059 Uiso 1 1 calc R . .
C8 C 0.7084(7) 0.6745(5) 0.38151(19) 0.0672(12) Uani 1 1 d . . .
H8A H 0.6544 0.7179 0.3458 0.101 Uiso 1 1 calc R . .
H8B H 0.7840 0.7535 0.3991 0.101 Uiso 1 1 calc R . .
H8C H 0.6201 0.6454 0.4103 0.101 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0818(7) 0.1034(9) 0.0359(4) 0.0063(5) -0.0123(5) -0.0160(7)
S1 0.0536(5) 0.0473(4) 0.0340(4) 0.0027(4) 0.0059(4) 0.0003(4)
Cl2 0.0566(6) 0.1845(17) 0.0678(7) 0.0350(9) 0.0037(6) -0.0282(8)
O1 0.0560(16) 0.0741(18) 0.0550(15) -0.0069(15) 0.0160(13) -0.0115(14)
O2 0.100(2) 0.0620(18) 0.0421(13) 0.0104(12) 0.0041(14) 0.0200(16)
F3 0.0429(10) 0.0498(11) 0.0491(10) -0.0001(10) -0.0069(9) -0.0012(9)
O4 0.0497(14) 0.0577(16) 0.0497(13) -0.0008(12) 0.0027(12) 0.0131(12)
C1 0.060(2) 0.066(2) 0.0375(17) 0.0109(17) 0.0091(18) 0.0031(19)
C2 0.062(2) 0.053(2) 0.0371(16) 0.0014(16) -0.0079(17) 0.0018(18)
C3 0.0479(19) 0.045(2) 0.0387(16) 0.0006(15) -0.0038(16) -0.0005(15)
C4 0.0481(18) 0.0300(16) 0.0355(14) 0.0000(13) 0.0018(15) 0.0018(14)
C5 0.0439(18) 0.0396(18) 0.0327(15) -0.0021(13) -0.0015(14) 0.0007(14)
C6 0.0421(18) 0.0396(18) 0.0330(14) -0.0017(13) -0.0041(15) 0.0042(15)
C7 0.054(2) 0.0370(18) 0.0292(14) 0.0017(13) 0.0009(15) 0.0041(15)
O8 0.0709(17) 0.0370(13) 0.0511(13) -0.0065(11) -0.0067(13) 0.0052(11)
C9 0.049(2) 0.073(3) 0.050(2) 0.012(2) 0.0038(19) 0.0004(19)
C10 0.050(2) 0.059(2) 0.0377(16) 0.0037(16) -0.0055(16) 0.0001(17)
C11 0.063(2) 0.057(2) 0.0357(16) -0.0069(15) 0.0033(17) -0.0071(19)
C12 0.059(2) 0.055(2) 0.0344(15) -0.0035(16) 0.0021(17) -0.0116(18)
C8 0.100(3) 0.037(2) 0.064(2) -0.0079(18) 0.003(2) 0.010(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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.745(4) . ?
S1 O2 1.422(3) . ?
S1 O1 1.427(3) . ?
S1 C11 1.778(4) . ?
S1 C6 1.879(3) . ?
Cl2 C9 1.743(4) . ?
F3 C6 1.372(4) . ?
O4 C7 1.199(4) . ?
C1 C9 1.369(5) . ?
C1 C2 1.374(6) . ?
C1 H1 0.9400 . ?
C2 C3 1.375(5) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9400 . ?
C4 C10 1.392(5) . ?
C4 C5 1.507(4) . ?
C5 C6 1.528(4) . ?
C5 C12 1.529(4) . ?
C5 H5 0.9900 . ?
C6 C7 1.525(4) . ?
C7 O8 1.314(4) . ?
O8 C8 1.454(5) . ?
C9 C10 1.378(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.529(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.9(2) . . ?
O2 S1 C11 110.97(19) . . ?
O1 S1 C11 111.78(18) . . ?
O2 S1 C6 108.32(15) . . ?
O1 S1 C6 108.13(16) . . ?
C11 S1 C6 96.24(16) . . ?
C9 C1 C2 117.4(3) . . ?
C9 C1 H1 121.3 . . ?
C2 C1 H1 121.3 . . ?
C1 C2 C3 122.2(3) . . ?
C1 C2 Cl1 118.7(3) . . ?
C3 C2 Cl1 119.1(3) . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C10 C4 C3 118.7(3) . . ?
C10 C4 C5 121.8(3) . . ?
C3 C4 C5 119.4(3) . . ?
C4 C5 C6 114.2(3) . . ?
C4 C5 C12 116.8(3) . . ?
C6 C5 C12 107.3(3) . . ?
C4 C5 H5 105.9 . . ?
C6 C5 H5 105.9 . . ?
C12 C5 H5 105.9 . . ?
F3 C6 C7 110.5(3) . . ?
F3 C6 C5 112.1(3) . . ?
C7 C6 C5 115.5(3) . . ?
F3 C6 S1 106.8(2) . . ?
C7 C6 S1 107.4(2) . . ?
C5 C6 S1 103.8(2) . . ?
O4 C7 O8 127.1(3) . . ?
O4 C7 C6 121.5(3) . . ?
O8 C7 C6 111.5(3) . . ?
C7 O8 C8 114.6(3) . . ?
C1 C9 C10 122.6(4) . . ?
C1 C9 Cl2 118.6(3) . . ?
C10 C9 Cl2 118.7(3) . . ?
C9 C10 C4 119.3(3) . . ?
C9 C10 H10 120.3 . . ?
C4 C10 H10 120.3 . . ?
C12 C11 S1 104.5(2) . . ?
C12 C11 H11A 110.9 . . ?
S1 C11 H11A 110.9 . . ?
C12 C11 H11B 110.9 . . ?
S1 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C11 C12 C5 107.1(3) . . ?
C11 C12 H12A 110.3 . . ?
C5 C12 H12A 110.3 . . ?
C11 C12 H12B 110.3 . . ?
C5 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
O8 C8 H8A 109.5 . . ?
O8 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O8 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 -0.2(6) . . . . ?
C9 C1 C2 Cl1 -179.0(3) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
Cl1 C2 C3 C4 178.9(3) . . . . ?
C2 C3 C4 C10 0.8(5) . . . . ?
C2 C3 C4 C5 -176.5(3) . . . . ?
C10 C4 C5 C6 123.0(3) . . . . ?
C3 C4 C5 C6 -59.8(4) . . . . ?
C10 C4 C5 C12 -3.3(5) . . . . ?
C3 C4 C5 C12 174.0(3) . . . . ?
C4 C5 C6 F3 81.8(3) . . . . ?
C12 C5 C6 F3 -147.1(3) . . . . ?
C4 C5 C6 C7 -46.0(4) . . . . ?
C12 C5 C6 C7 85.0(3) . . . . ?
C4 C5 C6 S1 -163.3(2) . . . . ?
C12 C5 C6 S1 -32.2(3) . . . . ?
O2 S1 C6 F3 -119.6(2) . . . . ?
O1 S1 C6 F3 10.4(3) . . . . ?
C11 S1 C6 F3 125.8(2) . . . . ?
O2 S1 C6 C7 -1.1(3) . . . . ?
O1 S1 C6 C7 129.0(2) . . . . ?
C11 S1 C6 C7 -115.6(3) . . . . ?
O2 S1 C6 C5 121.7(2) . . . . ?
O1 S1 C6 C5 -108.2(2) . . . . ?
C11 S1 C6 C5 7.2(2) . . . . ?
F3 C6 C7 O4 -166.3(3) . . . . ?
C5 C6 C7 O4 -37.6(4) . . . . ?
S1 C6 C7 O4 77.6(4) . . . . ?
F3 C6 C7 O8 14.7(4) . . . . ?
C5 C6 C7 O8 143.4(3) . . . . ?
S1 C6 C7 O8 -101.4(3) . . . . ?
O4 C7 O8 C8 -4.0(5) . . . . ?
C6 C7 O8 C8 174.9(3) . . . . ?
C2 C1 C9 C10 -0.8(7) . . . . ?
C2 C1 C9 Cl2 179.3(3) . . . . ?
C1 C9 C10 C4 1.8(6) . . . . ?
Cl2 C9 C10 C4 -178.3(3) . . . . ?
C3 C4 C10 C9 -1.8(5) . . . . ?
C5 C4 C10 C9 175.5(3) . . . . ?
O2 S1 C11 C12 -92.8(3) . . . . ?
O1 S1 C11 C12 131.9(3) . . . . ?
C6 S1 C11 C12 19.6(3) . . . . ?
S1 C11 C12 C5 -41.8(3) . . . . ?
C4 C5 C12 C11 179.0(3) . . . . ?
C6 C5 C12 C11 49.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        68.23
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 1020631'
