# Electronic Supplementary Material (ESI) for ChemComm.
# 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_ndr-km
_audit_creation_date             2013-10-14
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H22 O6 S'
_chemical_formula_sum            'C22 H22 O6 S'
_chemical_formula_weight         414.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 O2 S1'
_chemical_oxdiff_usercomment     '298K, COLORLESS BLOCK, 0.4 0.3 0.2'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.107(3)
_cell_length_b                   8.543(3)
_cell_length_c                   34.204(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.99(2)
_cell_angle_gamma                90.00
_cell_volume                     2065.3(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    860
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.7056
_cell_measurement_theta_min      3.8203
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            11955
_diffrn_reflns_theta_full        29.77
_diffrn_reflns_theta_max         29.77
_diffrn_reflns_theta_min         3.83
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9892
_diffrn_measured_fraction_theta_max 0.9071
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   20.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522  -99.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -46.00  -21.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522   77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega    0.00   50.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522   77.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega  -61.00  -35.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522 -178.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -84.00  -54.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522  178.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00    0.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522  -99.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -25.00   10.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522  -99.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
  8 omega  -33.00   27.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522   57.0000    0.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega  -86.00  -51.00   1.0000   15.4700
omega____ theta____ kappa____ phi______ frames
    -      -17.6522  -57.0000 -180.0000 35
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0879032000
_diffrn_orient_matrix_UB_12      0.0373625000
_diffrn_orient_matrix_UB_13      -0.0050110000
_diffrn_orient_matrix_UB_21      -0.0098904000
_diffrn_orient_matrix_UB_22      -0.0414360000
_diffrn_orient_matrix_UB_23      -0.0182393000
_diffrn_orient_matrix_UB_31      -0.0464664000
_diffrn_orient_matrix_UB_32      -0.0620907000
_diffrn_orient_matrix_UB_33      0.0087113000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2950
_reflns_number_total             4782
_reflns_odcompleteness_completeness 98.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4782
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0664
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.672
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0403P)²+1.1483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1420
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 1.01329(10) 0.88164(11) 0.35300(2) 0.0579(3) Uani 1 1 d . . .
O18 O 0.5241(3) 0.9839(3) 0.42339(7) 0.0671(7) Uani 1 1 d . . .
O16 O 0.7558(3) 1.0601(2) 0.46517(6) 0.0582(6) Uani 1 1 d . . .
O20 O 0.8447(3) 0.7496(2) 0.49929(5) 0.0530(5) Uani 1 1 d . . .
O14 O 0.9375(2) 0.5261(2) 0.39089(6) 0.0514(5) Uani 1 1 d . . .
O23 O 1.1314(2) 0.7348(2) 0.43628(6) 0.0508(5) Uani 1 1 d . . .
H23 H 1.0958 0.6730 0.4187 0.076 Uiso 1 1 calc R . .
O22 O 0.6826(3) 0.5805(2) 0.46023(6) 0.0628(6) Uani 1 1 d . . .
C15 C 0.6757(3) 0.9627(3) 0.43908(7) 0.0341(6) Uani 1 1 d . . .
C13 C 0.7747(3) 0.5705(3) 0.38608(7) 0.0344(6) Uani 1 1 d . . .
C3 C 0.7208(3) 0.7418(3) 0.39242(7) 0.0309(5) Uani 1 1 d . . .
H3 H 0.5829 0.7431 0.3923 0.037 Uiso 1 1 calc R . .
C24 C 0.6285(3) 0.4583(3) 0.36963(7) 0.0353(6) Uani 1 1 d . . .
C19 C 0.7683(3) 0.7004(3) 0.46505(8) 0.0377(6) Uani 1 1 d . . .
C2 C 0.7649(3) 0.8417(3) 0.35609(7) 0.0378(6) Uani 1 1 d . . .
H2 H 0.7025 0.9431 0.3583 0.045 Uiso 1 1 calc R . .
C4 C 0.8007(3) 0.8173(3) 0.43195(7) 0.0318(5) Uani 1 1 d . . .
C6 C 1.0542(4) 0.9753(4) 0.40018(9) 0.0508(8) Uani 1 1 d . . .
H6A H 1.1852 1.0087 0.4044 0.061 Uiso 1 1 calc R . .
H6B H 0.9752 1.0678 0.4003 0.061 Uiso 1 1 calc R . .
C5 C 1.0115(3) 0.8670(3) 0.43384(8) 0.0409(6) Uani 1 1 d . . .
H5 H 1.0402 0.9261 0.4583 0.049 Uiso 1 1 calc R . .
C25 C 0.6858(4) 0.3353(3) 0.34630(8) 0.0454(7) Uani 1 1 d . . .
H25 H 0.8128 0.3250 0.3425 0.055 Uiso 1 1 calc R . .
C29 C 0.4404(4) 0.4705(4) 0.37626(9) 0.0512(7) Uani 1 1 d . . .
H29 H 0.4007 0.5512 0.3917 0.061 Uiso 1 1 calc R . .
C17 C 0.6477(5) 1.1976(4) 0.47470(11) 0.0706(10) Uani 1 1 d . . .
H17A H 0.6240 1.2624 0.4518 0.106 Uiso 1 1 calc R . .
H17B H 0.7185 1.2559 0.4953 0.106 Uiso 1 1 calc R . .
H17C H 0.5295 1.1650 0.4833 0.106 Uiso 1 1 calc R . .
C21 C 0.8316(5) 0.6443(4) 0.53249(9) 0.0700(10) Uani 1 1 d . . .
H21A H 0.7759 0.5470 0.5232 0.105 Uiso 1 1 calc R . .
H21B H 0.7543 0.6913 0.5507 0.105 Uiso 1 1 calc R . .
H21C H 0.9559 0.6251 0.5454 0.105 Uiso 1 1 calc R . .
C26 C 0.5572(5) 0.2309(4) 0.32917(9) 0.0559(8) Uani 1 1 d . . .
H26 H 0.5949 0.1522 0.3129 0.067 Uiso 1 1 calc R . .
C7 C 0.6819(4) 0.7694(3) 0.31795(8) 0.0432(7) Uani 1 1 d . . .
C12 C 0.7844(5) 0.6703(4) 0.29516(9) 0.0614(9) Uani 1 1 d . . .
H12 H 0.9124 0.6532 0.3026 0.074 Uiso 1 1 calc R . .
C27 C 0.3711(5) 0.2438(4) 0.33632(10) 0.0616(9) Uani 1 1 d . . .
H27 H 0.2831 0.1719 0.3252 0.074 Uiso 1 1 calc R . .
C8 C 0.4953(5) 0.7952(4) 0.30658(9) 0.0639(9) Uani 1 1 d . . .
H8 H 0.4249 0.8608 0.3212 0.077 Uiso 1 1 calc R . .
C28 C 0.3128(4) 0.3622(4) 0.35987(11) 0.0650(9) Uani 1 1 d . . .
H28 H 0.1865 0.3686 0.3646 0.078 Uiso 1 1 calc R . .
C11 C 0.6984(7) 0.5980(5) 0.26206(10) 0.0832(12) Uani 1 1 d . . .
H11 H 0.7672 0.5320 0.2473 0.100 Uiso 1 1 calc R . .
C9 C 0.4122(7) 0.7227(6) 0.27313(13) 0.0967(14) Uani 1 1 d . . .
H9 H 0.2850 0.7407 0.2651 0.116 Uiso 1 1 calc R . .
C10 C 0.5141(8) 0.6240(6) 0.25138(12) 0.1010(15) Uani 1 1 d . . .
H10 H 0.4545 0.5751 0.2291 0.121 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 C2 1.812(3) . ?
S1 C6 1.797(3) . ?
O18 C15 1.167(3) . ?
O16 C15 1.306(3) . ?
O16 C17 1.459(3) . ?
O20 C19 1.308(3) . ?
O20 C21 1.460(3) . ?
O14 C13 1.213(3) . ?
O23 C5 1.412(3) . ?
O22 C19 1.194(3) . ?
C15 C4 1.561(3) . ?
C13 C3 1.534(3) . ?
C13 C24 1.481(3) . ?
C3 C2 1.566(3) . ?
C3 C4 1.551(3) . ?
C24 C25 1.405(4) . ?
C24 C29 1.383(4) . ?
C19 C4 1.545(4) . ?
C2 C7 1.507(4) . ?
C4 C5 1.552(3) . ?
C6 C5 1.532(4) . ?
C25 C26 1.365(4) . ?
C29 C28 1.373(4) . ?
C26 C27 1.374(4) . ?
C7 C12 1.405(4) . ?
C7 C8 1.360(4) . ?
C12 C11 1.375(5) . ?
C27 C28 1.383(5) . ?
C8 C9 1.379(5) . ?
C11 C10 1.341(6) . ?
C9 C10 1.379(6) . ?

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
C6 S1 C2 95.68(13) . . ?
C15 O16 C17 117.6(2) . . ?
C19 O20 C21 116.4(2) . . ?
O18 C15 O16 122.1(2) . . ?
O18 C15 C4 124.4(2) . . ?
O16 C15 C4 113.5(2) . . ?
O14 C13 C3 121.9(2) . . ?
O14 C13 C24 118.1(2) . . ?
C24 C13 C3 119.7(2) . . ?
C13 C3 C2 109.5(2) . . ?
C13 C3 C4 116.48(19) . . ?
C4 C3 C2 112.3(2) . . ?
C25 C24 C13 117.8(2) . . ?
C29 C24 C13 122.7(2) . . ?
C29 C24 C25 119.5(3) . . ?
O20 C19 C4 111.6(2) . . ?
O22 C19 O20 123.9(3) . . ?
O22 C19 C4 124.5(2) . . ?
C3 C2 S1 115.21(17) . . ?
C7 C2 S1 108.82(18) . . ?
C7 C2 C3 111.8(2) . . ?
C3 C4 C15 107.74(18) . . ?
C3 C4 C5 114.4(2) . . ?
C19 C4 C15 105.63(19) . . ?
C19 C4 C3 107.5(2) . . ?
C19 C4 C5 111.29(19) . . ?
C5 C4 C15 109.8(2) . . ?
C5 C6 S1 112.3(2) . . ?
O23 C5 C4 111.0(2) . . ?
O23 C5 C6 111.2(2) . . ?
C6 C5 C4 113.6(2) . . ?
C26 C25 C24 120.8(3) . . ?
C28 C29 C24 119.4(3) . . ?
C25 C26 C27 119.0(3) . . ?
C12 C7 C2 123.3(3) . . ?
C8 C7 C2 117.6(3) . . ?
C8 C7 C12 119.0(3) . . ?
C11 C12 C7 121.0(3) . . ?
C26 C27 C28 121.0(3) . . ?
C7 C8 C9 119.0(4) . . ?
C29 C28 C27 120.3(3) . . ?
C10 C11 C12 119.2(4) . . ?
C8 C9 C10 121.3(4) . . ?
C11 C10 C9 120.5(4) . . ?

_database_code_depnum_ccdc_archive 'CCDC 981071'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 F O3 S'
_chemical_formula_weight         368.41

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'
F F 0.0171 0.0103 '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                   9.10000(10)
_cell_length_b                   9.21500(10)
_cell_length_c                   11.4230(2)
_cell_angle_alpha                81.7180(10)
_cell_angle_beta                 70.6370(10)
_cell_angle_gamma                77.6340(10)
_cell_volume                     879.97(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8426
_cell_measurement_theta_min      2.411
_cell_measurement_theta_max      30.799

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9156
_exptl_absorpt_correction_T_max  0.9489
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15170
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3092
_reflns_number_gt                2735
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'



_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)+(0.0497P)²+0.2867P] 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_number_reflns         3092
_refine_ls_number_parameters     249
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_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
C1 C -0.09038(17) 0.20924(17) 0.54064(14) 0.0343(3) Uani 1 1 d . . .
C2 C 0.06114(17) 0.22511(16) 0.46531(14) 0.0329(3) Uani 1 1 d . . .
C3 C 0.17630(17) 0.16907(16) 0.52807(14) 0.0331(3) Uani 1 1 d . . .
C4 C 0.10958(18) 0.11651(17) 0.64867(15) 0.0352(3) Uani 1 1 d . . .
C5 C -0.23434(19) 0.2324(2) 0.50738(18) 0.0431(4) Uani 1 1 d . . .
C6 C 0.09413(17) 0.29590(17) 0.33681(14) 0.0339(3) Uani 1 1 d . . .
C7 C 0.0121(2) 0.43738(19) 0.31441(16) 0.0440(4) Uani 1 1 d . . .
H7 H -0.0597 0.4884 0.3807 0.053 Uiso 1 1 calc R . .
C8 C 0.0365(2) 0.5023(2) 0.19482(18) 0.0561(5) Uani 1 1 d . . .
H8 H -0.0194 0.5967 0.1809 0.067 Uiso 1 1 calc R . .
C9 C 0.1425(2) 0.4291(2) 0.09631(18) 0.0582(5) Uani 1 1 d . . .
H9 H 0.1571 0.4728 0.0156 0.070 Uiso 1 1 calc R . .
C10 C 0.2273(2) 0.2905(2) 0.11693(17) 0.0530(5) Uani 1 1 d . . .
H10 H 0.3007 0.2414 0.0501 0.064 Uiso 1 1 calc R . .
C11 C 0.2037(2) 0.22424(19) 0.23633(16) 0.0421(4) Uani 1 1 d . . .
H11 H 0.2618 0.1307 0.2496 0.051 Uiso 1 1 calc R . .
C12 C 0.18270(19) 0.04834(18) 0.74572(15) 0.0390(4) Uani 1 1 d . . .
C13 C 0.3057(2) 0.1021(2) 0.76239(17) 0.0470(4) Uani 1 1 d . A .
H13 H 0.3439 0.1835 0.7125 0.056 Uiso 1 1 calc R . .
C14 C 0.3695(2) 0.0326(3) 0.85397(19) 0.0602(6) Uani 1 1 d D . .
C15 C 0.3142(3) -0.0841(3) 0.9320(2) 0.0693(6) Uani 1 1 d . A .
H15 H 0.3585 -0.1281 0.9940 0.083 Uiso 1 1 calc R . .
C16 C 0.1918(3) -0.1345(3) 0.9164(2) 0.0670(6) Uani 1 1 d D . .
C17 C 0.1269(2) -0.0712(2) 0.82401(17) 0.0509(4) Uani 1 1 d . A .
H17 H 0.0451 -0.1088 0.8139 0.061 Uiso 1 1 calc R . .
C18 C 0.35033(17) 0.16582(17) 0.46515(15) 0.0360(3) Uani 1 1 d . . .
H18A H 0.4078 0.1139 0.5213 0.043 Uiso 1 1 calc R . .
H18B H 0.3844 0.1103 0.3919 0.043 Uiso 1 1 calc R . .
C19 C 0.39122(17) 0.31832(18) 0.42713(15) 0.0369(4) Uani 1 1 d . . .
C20 C 0.5672(2) 0.4600(2) 0.27793(19) 0.0574(5) Uani 1 1 d . . .
H20A H 0.6803 0.4446 0.2355 0.069 Uiso 1 1 calc R . .
H20B H 0.5449 0.5221 0.3457 0.069 Uiso 1 1 calc R . .
C21 C 0.4816(3) 0.5360(3) 0.1899(2) 0.0788(7) Uani 1 1 d . . .
H21A H 0.5147 0.6299 0.1577 0.118 Uiso 1 1 calc R . .
H21B H 0.3697 0.5525 0.2325 0.118 Uiso 1 1 calc R . .
H21C H 0.5046 0.4748 0.1226 0.118 Uiso 1 1 calc R . .
O1 O -0.35733(14) 0.20087(16) 0.57795(13) 0.0567(4) Uani 1 1 d . . .
O2 O 0.32067(15) 0.42696(14) 0.48013(13) 0.0594(4) Uani 1 1 d . . .
O3 O 0.51880(13) 0.31720(14) 0.32747(11) 0.0473(3) Uani 1 1 d . . .
S1 S -0.09207(5) 0.13174(5) 0.68628(4) 0.04072(15) Uani 1 1 d . . .
F1 F 0.4862(2) 0.0728(3) 0.87287(19) 0.0681(7) Uani 0.593(3) 1 d PD A 1
F1' F 0.1514(5) -0.2389(4) 0.9858(3) 0.0949(15) Uani 0.407(3) 1 d PD A 2
H5 H -0.228(2) 0.278(2) 0.4228(18) 0.049(5) Uiso 1 1 d . . .


_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
C1 C2 1.388(2) . ?
C1 C5 1.447(2) . ?
C1 S1 1.7098(16) . ?
C2 C3 1.428(2) . ?
C2 C6 1.479(2) . ?
C3 C4 1.371(2) . ?
C3 C18 1.502(2) . ?
C4 C12 1.475(2) . ?
C4 S1 1.7193(15) . ?
C5 O1 1.208(2) . ?
C5 H5 0.985(19) . ?
C6 C11 1.388(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.376(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.388(2) . ?
C12 C13 1.393(2) . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 F1 1.286(3) . ?
C14 C15 1.365(3) . ?
C15 C16 1.365(3) . ?
C15 H15 0.9300 . ?
C16 F1' 1.195(4) . ?
C16 C17 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.498(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O2 1.193(2) . ?
C19 O3 1.3288(19) . ?
C20 O3 1.454(2) . ?
C20 C21 1.480(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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 C1 C5 128.89(15) . . ?
C2 C1 S1 111.77(11) . . ?
C5 C1 S1 118.89(12) . . ?
C1 C2 C3 111.95(14) . . ?
C1 C2 C6 122.61(13) . . ?
C3 C2 C6 125.42(13) . . ?
C4 C3 C2 112.27(13) . . ?
C4 C3 C18 125.13(14) . . ?
C2 C3 C18 122.58(14) . . ?
C3 C4 C12 130.70(14) . . ?
C3 C4 S1 112.01(12) . . ?
C12 C4 S1 117.27(12) . . ?
O1 C5 C1 123.30(17) . . ?
O1 C5 H5 120.5(11) . . ?
C1 C5 H5 116.2(11) . . ?
C11 C6 C7 118.44(15) . . ?
C11 C6 C2 121.84(14) . . ?
C7 C6 C2 119.71(14) . . ?
C8 C7 C6 120.47(16) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.47(18) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.86(18) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.18(17) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.54(16) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C17 C12 C13 118.70(16) . . ?
C17 C12 C4 119.58(15) . . ?
C13 C12 C4 121.71(16) . . ?
C14 C13 C12 118.76(19) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
F1 C14 C15 114.7(2) . . ?
F1 C14 C13 122.5(2) . . ?
C15 C14 C13 122.8(2) . . ?
C16 C15 C14 118.06(19) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
F1' C16 C15 114.7(3) . . ?
F1' C16 C17 124.0(3) . . ?
C15 C16 C17 121.3(2) . . ?
C16 C17 C12 120.37(19) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C3 112.84(12) . . ?
C19 C18 H18A 109.0 . . ?
C3 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C3 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
O2 C19 O3 123.91(15) . . ?
O2 C19 C18 124.77(15) . . ?
O3 C19 C18 111.31(13) . . ?
O3 C20 C21 110.23(16) . . ?
O3 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
O3 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 O3 C20 116.73(14) . . ?
C1 S1 C4 91.99(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
C5 C1 C2 C3 -170.52(15) . . . . ?
S1 C1 C2 C3 1.52(17) . . . . ?
C5 C1 C2 C6 11.0(3) . . . . ?
S1 C1 C2 C6 -176.99(11) . . . . ?
C1 C2 C3 C4 -1.59(19) . . . . ?
C6 C2 C3 C4 176.87(14) . . . . ?
C1 C2 C3 C18 176.82(14) . . . . ?
C6 C2 C3 C18 -4.7(2) . . . . ?
C2 C3 C4 C12 179.28(15) . . . . ?
C18 C3 C4 C12 0.9(3) . . . . ?
C2 C3 C4 S1 0.95(17) . . . . ?
C18 C3 C4 S1 -177.41(12) . . . . ?
C2 C1 C5 O1 172.28(17) . . . . ?
S1 C1 C5 O1 0.7(2) . . . . ?
C1 C2 C6 C11 -125.65(17) . . . . ?
C3 C2 C6 C11 56.0(2) . . . . ?
C1 C2 C6 C7 53.3(2) . . . . ?
C3 C2 C6 C7 -124.96(17) . . . . ?
C11 C6 C7 C8 1.8(2) . . . . ?
C2 C6 C7 C8 -177.27(16) . . . . ?
C6 C7 C8 C9 -0.4(3) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C9 C10 C11 C6 0.2(3) . . . . ?
C7 C6 C11 C10 -1.7(2) . . . . ?
C2 C6 C11 C10 177.31(15) . . . . ?
C3 C4 C12 C17 -140.22(18) . . . . ?
S1 C4 C12 C17 38.0(2) . . . . ?
C3 C4 C12 C13 40.7(3) . . . . ?
S1 C4 C12 C13 -141.06(14) . . . . ?
C17 C12 C13 C14 1.4(2) . . . . ?
C4 C12 C13 C14 -179.46(16) . . . . ?
C12 C13 C14 F1 177.95(19) . . . . ?
C12 C13 C14 C15 -2.1(3) . . . . ?
F1 C14 C15 C16 -179.1(2) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 F1' 178.4(3) . . . . ?
C14 C15 C16 C17 0.8(3) . . . . ?
F1' C16 C17 C12 -178.8(3) . . . . ?
C15 C16 C17 C12 -1.4(3) . . . . ?
C13 C12 C17 C16 0.3(3) . . . . ?
C4 C12 C17 C16 -178.86(18) . . . . ?
C4 C3 C18 C19 -116.93(17) . . . . ?
C2 C3 C18 C19 64.88(19) . . . . ?
C3 C18 C19 O2 30.4(2) . . . . ?
C3 C18 C19 O3 -150.81(13) . . . . ?
O2 C19 O3 C20 -3.6(2) . . . . ?
C18 C19 O3 C20 177.54(14) . . . . ?
C21 C20 O3 C19 -86.4(2) . . . . ?
C2 C1 S1 C4 -0.85(12) . . . . ?
C5 C1 S1 C4 172.09(13) . . . . ?
C3 C4 S1 C1 -0.07(13) . . . . ?
C12 C4 S1 C1 -178.65(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 981072'
