# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_bo2327_crystal_2a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 F3 N O4 S'
_chemical_formula_sum            'C18 H14 F3 N O4 S'
_chemical_formula_weight         397.36

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1171(13)
_cell_length_b                   9.6587(18)
_cell_length_c                   11.5594(18)
_cell_angle_alpha                98.125(13)
_cell_angle_beta                 103.944(10)
_cell_angle_gamma                117.147(8)
_cell_volume                     841.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3053
_cell_measurement_theta_min      2.477
_cell_measurement_theta_max      29.127

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.45
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.8809
_exptl_absorpt_correction_T_max  0.8958
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10513
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         29.14
_reflns_number_total             4426
_reflns_number_gt                3747
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0569P)²+0.1690P] 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       0.005(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4426
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.50611(5) 0.97873(4) 0.80279(3) 0.02159(11) Uani 1 1 d . . .
F1 F 0.45104(14) 0.40368(12) 0.74994(9) 0.0376(2) Uani 1 1 d . . .
F2 F 0.06816(12) 0.15385(10) 0.96028(9) 0.0342(2) Uani 1 1 d . . .
F3 F 0.10050(13) 0.43896(12) 1.05981(9) 0.0374(2) Uani 1 1 d . . .
O1 O 0.37483(15) 1.02120(13) 0.76308(11) 0.0325(3) Uani 1 1 d . . .
O2 O 0.63154(15) 1.05887(12) 0.92673(10) 0.0312(3) Uani 1 1 d . . .
O3 O 0.20502(15) 0.34502(12) 0.31661(10) 0.0334(3) Uani 1 1 d . . .
O4 O 0.10989(15) 0.36454(13) 0.47595(11) 0.0373(3) Uani 1 1 d . . .
N1 N 0.40479(15) 0.78256(13) 0.78106(10) 0.0188(2) Uani 1 1 d . . .
C1 C 0.62023(18) 1.00622(15) 0.69707(12) 0.0190(3) Uani 1 1 d . . .
C2 C 0.76171(19) 1.16182(16) 0.72053(13) 0.0239(3) Uani 1 1 d . . .
H2 H 0.7918 1.2469 0.7904 0.029 Uiso 1 1 calc R . .
C3 C 0.85786(19) 1.19184(16) 0.64200(14) 0.0258(3) Uani 1 1 d . . .
H3 H 0.9537 1.2978 0.6569 0.031 Uiso 1 1 calc R . .
C4 C 0.8134(2) 1.06591(17) 0.54096(14) 0.0268(3) Uani 1 1 d . . .
H4 H 0.8806 1.0857 0.4875 0.032 Uiso 1 1 calc R . .
C5 C 0.67175(19) 0.91162(17) 0.51735(13) 0.0249(3) Uani 1 1 d . . .
H5 H 0.6429 0.8276 0.4471 0.030 Uiso 1 1 calc R . .
C6 C 0.56993(17) 0.87621(15) 0.59435(12) 0.0186(3) Uani 1 1 d . . .
C7 C 0.41397(17) 0.71117(15) 0.56705(12) 0.0177(3) Uani 1 1 d . . .
C8 C 0.30225(17) 0.69084(15) 0.64867(12) 0.0199(3) Uani 1 1 d . . .
H8A H 0.2186 0.7269 0.6170 0.024 Uiso 1 1 calc R . .
H8B H 0.2327 0.5740 0.6418 0.024 Uiso 1 1 calc R . .
C9 C 0.50547(19) 0.71652(16) 0.84863(13) 0.0235(3) Uani 1 1 d . . .
H9A H 0.5938 0.7988 0.9283 0.028 Uiso 1 1 calc R . .
H9B H 0.5683 0.6910 0.7981 0.028 Uiso 1 1 calc R . .
C10 C 0.38258(18) 0.56457(16) 0.87404(12) 0.0201(3) Uani 1 1 d . . .
C11 C 0.36220(19) 0.41484(17) 0.82581(13) 0.0225(3) Uani 1 1 d . . .
C12 C 0.25753(19) 0.27434(16) 0.85178(13) 0.0248(3) Uani 1 1 d . . .
H12 H 0.2468 0.1737 0.8166 0.030 Uiso 1 1 calc R . .
C13 C 0.17015(18) 0.28626(16) 0.93022(13) 0.0229(3) Uani 1 1 d . . .
C14 C 0.18600(19) 0.43303(17) 0.98052(13) 0.0233(3) Uani 1 1 d . . .
C15 C 0.28903(19) 0.57061(16) 0.95232(13) 0.0231(3) Uani 1 1 d . . .
H15 H 0.2967 0.6702 0.9861 0.028 Uiso 1 1 calc R . .
C16 C 0.37103(19) 0.59038(16) 0.46911(13) 0.0235(3) Uani 1 1 d . . .
H16 H 0.4481 0.6136 0.4228 0.028 Uiso 1 1 calc R . .
C17 C 0.21529(19) 0.42415(16) 0.42581(13) 0.0236(3) Uani 1 1 d . . .
C18 C 0.0521(2) 0.18413(18) 0.25671(16) 0.0375(4) Uani 1 1 d . . .
H18A H 0.0452 0.1172 0.3138 0.045 Uiso 1 1 calc R . .
H18B H 0.0613 0.1341 0.1810 0.045 Uiso 1 1 calc R . .
H18C H -0.0540 0.1921 0.2348 0.045 Uiso 1 1 calc R . .


_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 O1 1.4311(11) . ?
S1 O2 1.4312(11) . ?
S1 N1 1.6318(11) . ?
S1 C1 1.7603(14) . ?
F1 C11 1.3536(16) . ?
F2 C13 1.3480(15) . ?
F3 C14 1.3495(17) . ?
O3 C17 1.3384(17) . ?
O3 C18 1.4464(17) . ?
O4 C17 1.2036(17) . ?
N1 C8 1.4739(17) . ?
N1 C9 1.4795(17) . ?
C1 C2 1.3940(18) . ?
C1 C6 1.4098(19) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3863(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4020(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4952(18) . ?
C7 C16 1.3388(19) . ?
C7 C8 1.5163(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5084(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3834(19) . ?
C10 C15 1.397(2) . ?
C11 C12 1.3834(19) . ?
C12 C13 1.368(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(2) . ?
C14 C15 1.3731(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.4814(18) . ?
C16 H16 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
O1 S1 O2 119.00(7) . . ?
O1 S1 N1 107.47(7) . . ?
O2 S1 N1 109.22(6) . . ?
O1 S1 C1 107.90(7) . . ?
O2 S1 C1 108.61(7) . . ?
N1 S1 C1 103.54(6) . . ?
C17 O3 C18 115.97(12) . . ?
C8 N1 C9 114.81(11) . . ?
C8 N1 S1 112.14(8) . . ?
C9 N1 S1 117.24(9) . . ?
C2 C1 C6 122.22(13) . . ?
C2 C1 S1 116.66(11) . . ?
C6 C1 S1 121.11(10) . . ?
C3 C2 C1 119.78(13) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.47(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.58(14) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.76(14) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 116.17(12) . . ?
C5 C6 C7 121.87(12) . . ?
C1 C6 C7 121.94(12) . . ?
C16 C7 C6 120.21(12) . . ?
C16 C7 C8 122.22(12) . . ?
C6 C7 C8 117.45(11) . . ?
N1 C8 C7 113.76(11) . . ?
N1 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
N1 C9 C10 109.91(11) . . ?
N1 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
N1 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C15 116.84(12) . . ?
C11 C10 C9 122.14(13) . . ?
C15 C10 C9 120.97(12) . . ?
F1 C11 C10 118.78(12) . . ?
F1 C11 C12 117.31(12) . . ?
C10 C11 C12 123.91(13) . . ?
C13 C12 C11 117.29(13) . . ?
C13 C12 H12 121.4 . . ?
C11 C12 H12 121.4 . . ?
F2 C13 C12 119.94(13) . . ?
F2 C13 C14 119.11(13) . . ?
C12 C13 C14 120.94(13) . . ?
F3 C14 C15 120.66(13) . . ?
F3 C14 C13 118.54(13) . . ?
C15 C14 C13 120.78(13) . . ?
C14 C15 C10 120.22(13) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C7 C16 C17 126.48(13) . . ?
C7 C16 H16 116.8 . . ?
C17 C16 H16 116.8 . . ?
O4 C17 O3 123.14(13) . . ?
O4 C17 C16 127.89(13) . . ?
O3 C17 C16 108.97(12) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 S1 N1 C8 62.02(11) . . . . ?
O2 S1 N1 C8 -167.58(9) . . . . ?
C1 S1 N1 C8 -52.02(11) . . . . ?
O1 S1 N1 C9 -162.01(10) . . . . ?
O2 S1 N1 C9 -31.61(12) . . . . ?
C1 S1 N1 C9 83.96(11) . . . . ?
O1 S1 C1 C2 86.44(12) . . . . ?
O2 S1 C1 C2 -43.84(12) . . . . ?
N1 S1 C1 C2 -159.84(11) . . . . ?
O1 S1 C1 C6 -93.71(12) . . . . ?
O2 S1 C1 C6 136.01(11) . . . . ?
N1 S1 C1 C6 20.01(13) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
S1 C1 C2 C3 179.54(11) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C4 C5 C6 C7 178.20(13) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
S1 C1 C6 C5 -179.14(10) . . . . ?
C2 C1 C6 C7 -177.67(12) . . . . ?
S1 C1 C6 C7 2.49(18) . . . . ?
C5 C6 C7 C16 2.2(2) . . . . ?
C1 C6 C7 C16 -179.52(13) . . . . ?
C5 C6 C7 C8 -173.82(12) . . . . ?
C1 C6 C7 C8 4.45(19) . . . . ?
C9 N1 C8 C7 -71.97(14) . . . . ?
S1 N1 C8 C7 65.12(13) . . . . ?
C16 C7 C8 N1 145.48(13) . . . . ?
C6 C7 C8 N1 -38.58(16) . . . . ?
C8 N1 C9 C10 -74.43(14) . . . . ?
S1 N1 C9 C10 150.74(10) . . . . ?
N1 C9 C10 C11 118.00(15) . . . . ?
N1 C9 C10 C15 -64.68(16) . . . . ?
C15 C10 C11 F1 -179.73(12) . . . . ?
C9 C10 C11 F1 -2.3(2) . . . . ?
C15 C10 C11 C12 -0.7(2) . . . . ?
C9 C10 C11 C12 176.73(13) . . . . ?
F1 C11 C12 C13 178.88(12) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 F2 -179.08(12) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
F2 C13 C14 F3 1.0(2) . . . . ?
C12 C13 C14 F3 -178.36(13) . . . . ?
F2 C13 C14 C15 179.84(13) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
F3 C14 C15 C10 177.44(13) . . . . ?
C13 C14 C15 C10 -1.4(2) . . . . ?
C11 C10 C15 C14 1.4(2) . . . . ?
C9 C10 C15 C14 -176.02(13) . . . . ?
C6 C7 C16 C17 -176.06(13) . . . . ?
C8 C7 C16 C17 -0.2(2) . . . . ?
C18 O3 C17 O4 3.6(2) . . . . ?
C18 O3 C17 C16 -175.57(13) . . . . ?
C7 C16 C17 O4 -7.0(3) . . . . ?
C7 C16 C17 O3 172.14(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 982259'
#######################################################################
#
#                 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_bo2326_crystal_4a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H14 F3 N O4 S'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C18 H14 F3 N O4 S'
_chemical_formula_weight         397.36
_chemical_melting_point          ?

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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.947(5)
_cell_length_b                   8.529(2)
_cell_length_c                   22.067(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.800(3)
_cell_angle_gamma                90.00
_cell_volume                     3333.8(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5980
_cell_measurement_theta_min      2.682
_cell_measurement_theta_max      29.127

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   multiiscans
_exptl_absorpt_correction_T_min  0.8633
_exptl_absorpt_correction_T_max  0.9202
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17852
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         29.13
_reflns_number_total             4476
_reflns_number_gt                4114
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0681P)²+2.3600P] 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       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4476
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.433426(19) 0.45134(4) 0.588127(17) 0.02185(12) Uani 1 1 d . . .
F1 F 0.52472(7) 0.98739(13) 0.57148(5) 0.0432(3) Uani 1 1 d . . .
F2 F 0.59846(7) 1.12414(16) 0.79182(7) 0.0603(4) Uani 1 1 d . . .
F3 F 0.61385(6) 0.81867(17) 0.82452(5) 0.0512(3) Uani 1 1 d . . .
O1 O 0.45696(6) 0.32852(13) 0.55483(6) 0.0315(3) Uani 1 1 d . . .
O2 O 0.46244(7) 0.44377(14) 0.65745(5) 0.0348(3) Uani 1 1 d . . .
O3 O 0.27522(7) 0.71296(13) 0.29579(5) 0.0289(2) Uani 1 1 d . . .
O4 O 0.29496(7) 0.48468(13) 0.34970(5) 0.0322(3) Uani 1 1 d . . .
N1 N 0.45661(6) 0.62343(14) 0.56659(6) 0.0220(3) Uani 1 1 d . . .
C1 C 0.33518(8) 0.46315(16) 0.55668(6) 0.0192(3) Uani 1 1 d . . .
C2 C 0.29617(8) 0.36961(17) 0.58590(7) 0.0232(3) Uani 1 1 d . . .
H2 H 0.3225 0.3151 0.6250 0.028 Uiso 1 1 calc R . .
C3 C 0.21831(9) 0.35690(18) 0.55733(7) 0.0255(3) Uani 1 1 d . . .
H3 H 0.1908 0.2935 0.5766 0.031 Uiso 1 1 calc R . .
C4 C 0.18091(8) 0.43812(17) 0.50013(8) 0.0251(3) Uani 1 1 d . . .
H4 H 0.1276 0.4291 0.4804 0.030 Uiso 1 1 calc R . .
C5 C 0.21993(8) 0.53165(17) 0.47154(7) 0.0219(3) Uani 1 1 d . . .
H5 H 0.1929 0.5860 0.4326 0.026 Uiso 1 1 calc R . .
C6 C 0.29897(8) 0.54782(15) 0.49904(6) 0.0186(3) Uani 1 1 d . . .
C7 C 0.34199(8) 0.64970(16) 0.47185(6) 0.0190(3) Uani 1 1 d . . .
C8 C 0.41467(8) 0.68378(16) 0.50540(6) 0.0208(3) Uani 1 1 d . . .
H8 H 0.4394 0.7541 0.4861 0.025 Uiso 1 1 calc R . .
C9 C 0.53798(8) 0.66477(18) 0.59684(7) 0.0256(3) Uani 1 1 d . . .
H9A H 0.5562 0.7045 0.5628 0.031 Uiso 1 1 calc R . .
H9B H 0.5670 0.5688 0.6154 0.031 Uiso 1 1 calc R . .
C10 C 0.55319(7) 0.78635(18) 0.64936(7) 0.0236(3) Uani 1 1 d . . .
C11 C 0.54641(9) 0.94470(19) 0.63472(8) 0.0295(3) Uani 1 1 d . . .
C12 C 0.56031(10) 1.0614(2) 0.68058(10) 0.0377(4) Uani 1 1 d . . .
H12 H 0.5540 1.1689 0.6686 0.045 Uiso 1 1 calc R . .
C13 C 0.58370(10) 1.0158(2) 0.74448(9) 0.0385(4) Uani 1 1 d . . .
C14 C 0.59138(9) 0.8594(2) 0.76121(8) 0.0345(4) Uani 1 1 d . . .
C15 C 0.57594(8) 0.7441(2) 0.71467(7) 0.0279(3) Uani 1 1 d . . .
H15 H 0.5807 0.6367 0.7269 0.033 Uiso 1 1 calc R . .
C16 C 0.30488(8) 0.73047(17) 0.40765(6) 0.0221(3) Uani 1 1 d . . .
H16A H 0.3370 0.8196 0.4047 0.026 Uiso 1 1 calc R . .
H16B H 0.2558 0.7737 0.4062 0.026 Uiso 1 1 calc R . .
C17 C 0.29146(7) 0.62547(17) 0.34934(6) 0.0206(3) Uani 1 1 d . . .
C18 C 0.26519(10) 0.6300(2) 0.23606(7) 0.0328(4) Uani 1 1 d . . .
H18A H 0.3140 0.5891 0.2372 0.039 Uiso 1 1 calc R . .
H18B H 0.2449 0.7019 0.1993 0.039 Uiso 1 1 calc R . .
H18C H 0.2299 0.5428 0.2313 0.039 Uiso 1 1 calc R . .


_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 O2 1.4316(12) . ?
S1 O1 1.4383(12) . ?
S1 N1 1.6497(13) . ?
S1 C1 1.7434(15) . ?
F1 C11 1.357(2) . ?
F2 C13 1.3474(19) . ?
F3 C14 1.353(2) . ?
O3 C17 1.3378(17) . ?
O3 C18 1.4478(18) . ?
O4 C17 1.2025(19) . ?
N1 C8 1.3992(17) . ?
N1 C9 1.4886(17) . ?
C1 C2 1.392(2) . ?
C1 C6 1.4109(19) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4088(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4583(19) . ?
C7 C8 1.3434(19) . ?
C7 C16 1.5063(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.505(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.384(2) . ?
C10 C15 1.397(2) . ?
C11 C12 1.377(2) . ?
C12 C13 1.376(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C14 C15 1.376(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.5133(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 116.23(7) . . ?
O2 S1 N1 107.91(7) . . ?
O1 S1 N1 109.77(7) . . ?
O2 S1 C1 112.23(7) . . ?
O1 S1 C1 108.64(7) . . ?
N1 S1 C1 100.95(6) . . ?
C17 O3 C18 116.51(12) . . ?
C8 N1 C9 119.24(12) . . ?
C8 N1 S1 119.16(10) . . ?
C9 N1 S1 114.89(10) . . ?
C2 C1 C6 122.88(13) . . ?
C2 C1 S1 116.75(11) . . ?
C6 C1 S1 119.80(11) . . ?
C3 C2 C1 119.22(13) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.32(14) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.20(14) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.25(13) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 116.13(13) . . ?
C5 C6 C7 123.04(12) . . ?
C1 C6 C7 120.80(12) . . ?
C8 C7 C6 121.03(12) . . ?
C8 C7 C16 117.66(13) . . ?
C6 C7 C16 121.13(12) . . ?
C7 C8 N1 124.89(13) . . ?
C7 C8 H8 117.6 . . ?
N1 C8 H8 117.6 . . ?
N1 C9 C10 113.15(12) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 117.48(14) . . ?
C11 C10 C9 121.08(14) . . ?
C15 C10 C9 121.43(14) . . ?
F1 C11 C12 118.10(15) . . ?
F1 C11 C10 118.10(14) . . ?
C12 C11 C10 123.80(16) . . ?
C13 C12 C11 117.20(17) . . ?
C13 C12 H12 121.4 . . ?
C11 C12 H12 121.4 . . ?
F2 C13 C12 120.24(19) . . ?
F2 C13 C14 118.88(18) . . ?
C12 C13 C14 120.88(15) . . ?
F3 C14 C15 119.49(17) . . ?
F3 C14 C13 119.34(16) . . ?
C15 C14 C13 121.17(16) . . ?
C14 C15 C10 119.45(16) . . ?
C14 C15 H15 120.3 . . ?
C10 C15 H15 120.3 . . ?
C7 C16 C17 114.23(12) . . ?
C7 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C7 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
O4 C17 O3 123.90(13) . . ?
O4 C17 C16 126.38(13) . . ?
O3 C17 C16 109.72(12) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O2 S1 N1 C8 -157.74(11) . . . . ?
O1 S1 N1 C8 74.69(12) . . . . ?
C1 S1 N1 C8 -39.86(12) . . . . ?
O2 S1 N1 C9 51.15(12) . . . . ?
O1 S1 N1 C9 -76.43(11) . . . . ?
C1 S1 N1 C9 169.02(10) . . . . ?
O2 S1 C1 C2 -40.80(13) . . . . ?
O1 S1 C1 C2 89.14(12) . . . . ?
N1 S1 C1 C2 -155.47(11) . . . . ?
O2 S1 C1 C6 147.55(11) . . . . ?
O1 S1 C1 C6 -82.52(12) . . . . ?
N1 S1 C1 C6 32.88(12) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
S1 C1 C2 C3 -170.81(11) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C7 -177.63(13) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
S1 C1 C6 C5 170.51(10) . . . . ?
C2 C1 C6 C7 177.27(13) . . . . ?
S1 C1 C6 C7 -11.60(18) . . . . ?
C5 C6 C7 C8 167.88(13) . . . . ?
C1 C6 C7 C8 -9.9(2) . . . . ?
C5 C6 C7 C16 -7.2(2) . . . . ?
C1 C6 C7 C16 175.10(12) . . . . ?
C6 C7 C8 N1 2.5(2) . . . . ?
C16 C7 C8 N1 177.71(13) . . . . ?
C9 N1 C8 C7 176.87(13) . . . . ?
S1 N1 C8 C7 27.01(19) . . . . ?
C8 N1 C9 C10 103.37(15) . . . . ?
S1 N1 C9 C10 -105.55(13) . . . . ?
N1 C9 C10 C11 -84.75(17) . . . . ?
N1 C9 C10 C15 96.41(16) . . . . ?
C15 C10 C11 F1 179.67(13) . . . . ?
C9 C10 C11 F1 0.8(2) . . . . ?
C15 C10 C11 C12 -0.4(2) . . . . ?
C9 C10 C11 C12 -179.27(15) . . . . ?
F1 C11 C12 C13 -178.72(15) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C11 C12 C13 F2 179.84(15) . . . . ?
C11 C12 C13 C14 -1.1(3) . . . . ?
F2 C13 C14 F3 -0.3(2) . . . . ?
C12 C13 C14 F3 -179.39(15) . . . . ?
F2 C13 C14 C15 179.04(15) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
F3 C14 C15 C10 -179.62(13) . . . . ?
C13 C14 C15 C10 1.0(2) . . . . ?
C11 C10 C15 C14 -0.8(2) . . . . ?
C9 C10 C15 C14 178.09(14) . . . . ?
C8 C7 C16 C17 106.98(15) . . . . ?
C6 C7 C16 C17 -77.82(16) . . . . ?
C18 O3 C17 O4 -3.1(2) . . . . ?
C18 O3 C17 C16 176.48(12) . . . . ?
C7 C16 C17 O4 13.9(2) . . . . ?
C7 C16 C17 O3 -165.64(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 982260'
