# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20150128-sai4
_database_code_depnum_ccdc_archive 'CCDC 1415530'
_audit_update_record             
;
2015-07-28 deposited with the CCDC.
2015-12-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C17 H23 F2 N O5 S'
_chemical_formula_moiety         'C17 H23 F2 N O5 S'
_chemical_formula_weight         391.43
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   38.0429(9)
_cell_length_b                   5.96446(15)
_cell_length_c                   19.5829(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 120.9238(7)
_cell_angle_gamma                90.0000
_cell_volume                     3811.84(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13082
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      27.45
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648.00
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            17940
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4346
_reflns_number_gt                3272
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1951
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4346
_refine_ls_number_parameters     235
_refine_ls_goodness_of_fit_ref   1.411
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.449214(17) 0.35099(10) 0.16585(4) 0.0436(3) Uani 1.0 8 d . . .
F1 F 0.38697(4) 0.1475(2) 0.16256(9) 0.0481(4) Uani 1.0 8 d . . .
F12 F 0.41213(6) 0.2007(5) 0.33593(14) 0.1010(8) Uani 1.0 8 d . . .
O2 O 0.37356(5) 0.6293(3) 0.04903(10) 0.0418(4) Uani 1.0 8 d . . .
O3 O 0.35722(5) 0.0385(3) 0.31965(11) 0.0510(5) Uani 1.0 8 d . . .
O11 O 0.33821(5) 0.3057(3) 0.01975(11) 0.0527(5) Uani 1.0 8 d . . .
O20 O 0.26096(5) 0.8389(3) 0.09895(10) 0.0393(4) Uani 1.0 8 d . . .
O21 O 0.23705(4) 0.5188(3) 0.15400(9) 0.0367(4) Uani 1.0 8 d . . .
N23 N 0.44073(7) 0.2279(4) 0.08096(15) 0.0516(6) Uani 1.0 8 d . . .
C1 C 0.29029(6) 0.6863(4) 0.14466(12) 0.0321(5) Uani 1.0 8 d . . .
C3 C 0.39808(6) 0.3605(4) 0.15032(14) 0.0355(5) Uani 1.0 8 d . . .
C4 C 0.27756(6) 0.5158(4) 0.17705(12) 0.0316(5) Uani 1.0 8 d . . .
C5 C 0.30578(7) 0.3631(4) 0.22852(13) 0.0346(5) Uani 1.0 8 d . . .
C6 C 0.32989(7) 0.6866(4) 0.15964(13) 0.0344(5) Uani 1.0 8 d . . .
C7 C 0.34651(7) 0.3671(4) 0.24529(12) 0.0369(5) Uani 1.0 8 d . . .
C8 C 0.36616(6) 0.4225(4) 0.06493(13) 0.0362(5) Uani 1.0 8 d . . .
C9 C 0.35852(6) 0.5258(4) 0.20842(12) 0.0363(5) Uani 1.0 8 d . . .
C10 C 0.39938(6) 0.5220(4) 0.21248(13) 0.0394(5) Uani 1.0 8 d . . .
C13 C 0.27076(8) 1.0066(4) 0.05919(15) 0.0440(6) Uani 1.0 8 d . . .
C14 C 0.37540(8) 0.2029(5) 0.30239(15) 0.0495(7) Uani 1.0 8 d . . .
C15 C 0.34464(9) 0.7152(5) -0.02930(16) 0.0572(7) Uani 1.0 8 d . . .
C16 C 0.45285(9) -0.0105(5) 0.0903(3) 0.0653(9) Uani 1.0 8 d . . .
C17 C 0.45227(12) 0.3693(5) 0.0345(3) 0.0708(10) Uani 1.0 8 d . . .
C18 C 0.49891(9) -0.0571(6) 0.1389(3) 0.0872(13) Uani 1.0 8 d . . .
C19 C 0.4341(2) 0.3050(9) -0.0492(3) 0.123(2) Uani 1.0 8 d . . .
C22 C 0.22192(7) 0.3315(4) 0.17662(15) 0.0427(6) Uani 1.0 8 d . . .
H5 H 0.2978 0.2535 0.2531 0.0415 Uiso 1.0 8 calc R . .
H6 H 0.3379 0.7994 0.1361 0.0413 Uiso 1.0 8 calc R . .
H10A H 0.4211 0.4745 0.2663 0.0473 Uiso 1.0 8 calc R . .
H10B H 0.4061 0.6748 0.2029 0.0473 Uiso 1.0 8 calc R . .
H13A H 0.2937 1.0978 0.0987 0.0528 Uiso 1.0 8 calc R . .
H13B H 0.2468 1.1027 0.0277 0.0528 Uiso 1.0 8 calc R . .
H13C H 0.2785 0.9343 0.0239 0.0528 Uiso 1.0 8 calc R . .
H15A H 0.3167 0.6940 -0.0401 0.0686 Uiso 1.0 8 calc R . .
H15B H 0.3479 0.6345 -0.0693 0.0686 Uiso 1.0 8 calc R . .
H15C H 0.3497 0.8754 -0.0316 0.0686 Uiso 1.0 8 calc R . .
H16A H 0.4418 -0.0761 0.0366 0.0783 Uiso 1.0 8 calc R . .
H16B H 0.4397 -0.0896 0.1157 0.0783 Uiso 1.0 8 calc R . .
H17A H 0.4825 0.3664 0.0600 0.0850 Uiso 1.0 8 calc R . .
H17B H 0.4442 0.5257 0.0367 0.0850 Uiso 1.0 8 calc R . .
H18A H 0.5036 -0.2194 0.1438 0.1046 Uiso 1.0 8 calc R . .
H18B H 0.5104 0.0088 0.1921 0.1046 Uiso 1.0 8 calc R . .
H18C H 0.5122 0.0095 0.1121 0.1046 Uiso 1.0 8 calc R . .
H19A H 0.4042 0.3131 -0.0759 0.1480 Uiso 1.0 8 calc R . .
H19B H 0.4423 0.1515 -0.0524 0.1480 Uiso 1.0 8 calc R . .
H19C H 0.4437 0.4075 -0.0754 0.1480 Uiso 1.0 8 calc R . .
H22A H 0.1926 0.3517 0.1562 0.0512 Uiso 1.0 8 calc R . .
H22B H 0.2367 0.3203 0.2348 0.0512 Uiso 1.0 8 calc R . .
H22C H 0.2261 0.1939 0.1543 0.0512 Uiso 1.0 8 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 N23 1.690(3) yes . .
S1 C3 1.809(3) yes . .
F1 C3 1.398(3) yes . .
F12 C14 1.200(4) yes . .
O2 C8 1.337(3) yes . .
O2 C15 1.446(3) yes . .
O3 C14 1.340(4) yes . .
O11 C8 1.197(3) yes . .
O20 C1 1.359(3) yes . .
O20 C13 1.430(4) yes . .
O21 C4 1.365(3) yes . .
O21 C22 1.427(4) yes . .
N23 C16 1.477(4) yes . .
N23 C17 1.464(6) yes . .
C1 C4 1.410(4) yes . .
C1 C6 1.379(4) yes . .
C3 C8 1.523(3) yes . .
C3 C10 1.533(4) yes . .
C4 C5 1.374(3) yes . .
C5 C7 1.409(4) yes . .
C6 C9 1.396(3) yes . .
C7 C9 1.402(4) yes . .
C7 C14 1.468(4) yes . .
C9 C10 1.515(4) yes . .
C16 C18 1.530(4) yes . .
C17 C19 1.465(7) yes . .
C5 H5 0.950 no . .
C6 H6 0.950 no . .
C10 H10A 0.990 no . .
C10 H10B 0.990 no . .
C13 H13A 0.980 no . .
C13 H13B 0.980 no . .
C13 H13C 0.980 no . .
C15 H15A 0.980 no . .
C15 H15B 0.980 no . .
C15 H15C 0.980 no . .
C16 H16A 0.990 no . .
C16 H16B 0.990 no . .
C17 H17A 0.990 no . .
C17 H17B 0.990 no . .
C18 H18A 0.980 no . .
C18 H18B 0.980 no . .
C18 H18C 0.980 no . .
C19 H19A 0.980 no . .
C19 H19B 0.980 no . .
C19 H19C 0.980 no . .
C22 H22A 0.980 no . .
C22 H22B 0.980 no . .
C22 H22C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N23 S1 C3 101.71(12) yes . . .
C8 O2 C15 115.95(18) yes . . .
C1 O20 C13 118.1(3) yes . . .
C4 O21 C22 117.00(16) yes . . .
S1 N23 C16 114.0(3) yes . . .
S1 N23 C17 113.23(19) yes . . .
C16 N23 C17 117.2(4) yes . . .
O20 C1 C4 115.1(2) yes . . .
O20 C1 C6 125.2(3) yes . . .
C4 C1 C6 119.71(18) yes . . .
S1 C3 F1 109.67(14) yes . . .
S1 C3 C8 112.0(2) yes . . .
S1 C3 C10 107.04(13) yes . . .
F1 C3 C8 105.55(15) yes . . .
F1 C3 C10 108.9(3) yes . . .
C8 C3 C10 113.66(18) yes . . .
O21 C4 C1 115.62(17) yes . . .
O21 C4 C5 125.1(3) yes . . .
C1 C4 C5 119.3(3) yes . . .
C4 C5 C7 120.7(3) yes . . .
C1 C6 C9 121.8(3) yes . . .
C5 C7 C9 120.12(19) yes . . .
C5 C7 C14 118.0(3) yes . . .
C9 C7 C14 121.9(3) yes . . .
O2 C8 O11 125.3(2) yes . . .
O2 C8 C3 109.58(16) yes . . .
O11 C8 C3 125.1(3) yes . . .
C6 C9 C7 118.0(3) yes . . .
C6 C9 C10 117.7(3) yes . . .
C7 C9 C10 124.07(19) yes . . .
C3 C10 C9 110.73(17) yes . . .
F12 C14 O3 117.4(3) yes . . .
F12 C14 C7 129.0(3) yes . . .
O3 C14 C7 113.5(3) yes . . .
N23 C16 C18 115.9(3) yes . . .
N23 C17 C19 115.2(4) yes . . .
C4 C5 H5 119.647 no . . .
C7 C5 H5 119.632 no . . .
C1 C6 H6 119.084 no . . .
C9 C6 H6 119.078 no . . .
C3 C10 H10A 109.495 no . . .
C3 C10 H10B 109.485 no . . .
C9 C10 H10A 109.513 no . . .
C9 C10 H10B 109.510 no . . .
H10A C10 H10B 108.061 no . . .
O20 C13 H13A 109.471 no . . .
O20 C13 H13B 109.484 no . . .
O20 C13 H13C 109.474 no . . .
H13A C13 H13B 109.470 no . . .
H13A C13 H13C 109.456 no . . .
H13B C13 H13C 109.471 no . . .
O2 C15 H15A 109.473 no . . .
O2 C15 H15B 109.479 no . . .
O2 C15 H15C 109.475 no . . .
H15A C15 H15B 109.458 no . . .
H15A C15 H15C 109.458 no . . .
H15B C15 H15C 109.485 no . . .
N23 C16 H16A 108.317 no . . .
N23 C16 H16B 108.305 no . . .
C18 C16 H16A 108.309 no . . .
C18 C16 H16B 108.305 no . . .
H16A C16 H16B 107.410 no . . .
N23 C17 H17A 108.489 no . . .
N23 C17 H17B 108.477 no . . .
C19 C17 H17A 108.492 no . . .
C19 C17 H17B 108.479 no . . .
H17A C17 H17B 107.497 no . . .
C16 C18 H18A 109.467 no . . .
C16 C18 H18B 109.466 no . . .
C16 C18 H18C 109.460 no . . .
H18A C18 H18B 109.476 no . . .
H18A C18 H18C 109.481 no . . .
H18B C18 H18C 109.477 no . . .
C17 C19 H19A 109.475 no . . .
C17 C19 H19B 109.464 no . . .
C17 C19 H19C 109.465 no . . .
H19A C19 H19B 109.470 no . . .
H19A C19 H19C 109.483 no . . .
H19B C19 H19C 109.470 no . . .
O21 C22 H22A 109.468 no . . .
O21 C22 H22B 109.466 no . . .
O21 C22 H22C 109.480 no . . .
H22A C22 H22B 109.474 no . . .
H22A C22 H22C 109.468 no . . .
H22B C22 H22C 109.471 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N23 S1 C3 F1 76.43(17) no . . . .
N23 S1 C3 C8 -40.38(15) no . . . .
N23 S1 C3 C10 -165.56(13) no . . . .
C3 S1 N23 C16 -103.50(17) no . . . .
C3 S1 N23 C17 119.09(15) no . . . .
C15 O2 C8 O11 0.7(5) no . . . .
C15 O2 C8 C3 -177.6(3) no . . . .
C13 O20 C1 C4 -175.31(17) no . . . .
C13 O20 C1 C6 3.7(3) no . . . .
C22 O21 C4 C1 171.50(18) no . . . .
C22 O21 C4 C5 -8.9(3) no . . . .
S1 N23 C16 C18 -69.3(4) no . . . .
S1 N23 C17 C19 -161.4(2) no . . . .
C16 N23 C17 C19 62.6(4) no . . . .
C17 N23 C16 C18 66.3(4) no . . . .
O20 C1 C4 O21 4.1(3) no . . . .
O20 C1 C4 C5 -175.50(17) no . . . .
O20 C1 C6 C9 178.95(19) no . . . .
C4 C1 C6 C9 -2.1(4) no . . . .
C6 C1 C4 O21 -175.02(19) no . . . .
C6 C1 C4 C5 5.4(4) no . . . .
S1 C3 C8 O2 -63.2(3) no . . . .
S1 C3 C8 O11 118.4(3) no . . . .
S1 C3 C10 C9 -175.28(13) no . . . .
F1 C3 C8 O2 177.6(2) no . . . .
F1 C3 C8 O11 -0.8(4) no . . . .
F1 C3 C10 C9 -56.78(19) no . . . .
C8 C3 C10 C9 60.6(3) no . . . .
C10 C3 C8 O2 58.3(3) no . . . .
C10 C3 C8 O11 -120.1(3) no . . . .
O21 C4 C5 C7 176.58(19) no . . . .
C1 C4 C5 C7 -3.9(4) no . . . .
C4 C5 C7 C9 -1.0(4) no . . . .
C4 C5 C7 C14 178.45(19) no . . . .
C1 C6 C9 C7 -2.8(4) no . . . .
C1 C6 C9 C10 172.14(19) no . . . .
C5 C7 C9 C6 4.3(4) no . . . .
C5 C7 C9 C10 -170.27(19) no . . . .
C5 C7 C14 F12 -165.2(3) no . . . .
C5 C7 C14 O3 12.9(4) no . . . .
C9 C7 C14 F12 14.3(5) no . . . .
C9 C7 C14 O3 -167.7(3) no . . . .
C14 C7 C9 C6 -175.1(2) no . . . .
C14 C7 C9 C10 10.3(4) no . . . .
C6 C9 C10 C3 -92.0(3) no . . . .
C7 C9 C10 C3 82.6(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 O2 3.0830(16) no . .
S1 C18 3.286(5) no . .
F1 F12 3.034(4) no . .
F1 O2 3.507(3) no . .
F1 O11 2.612(3) no . .
F1 N23 3.213(4) no . .
F1 C7 3.045(4) no . .
F1 C9 2.840(3) no . .
F1 C14 3.007(4) no . .
F1 C16 3.581(5) no . .
F12 C3 3.523(4) no . .
F12 C9 2.987(3) no . .
F12 C10 2.924(4) no . .
O2 N23 3.318(3) no . .
O2 C6 3.357(4) no . .
O2 C9 3.505(4) no . .
O2 C10 2.896(4) no . .
O2 C17 3.511(6) no . .
O3 C5 2.678(3) no . .
O11 N23 3.473(4) no . .
O11 C10 3.507(3) no . .
O11 C15 2.682(4) no . .
O20 O21 2.577(3) no . .
O20 C5 3.599(3) no . .
N23 C8 2.929(4) no . .
C1 C7 2.784(3) no . .
C3 C6 3.322(4) no . .
C3 C7 3.326(5) no . .
C4 C9 2.815(4) no . .
C5 C6 2.767(4) no . .
C5 C22 2.813(4) no . .
C6 C8 3.234(4) no . .
C6 C13 2.833(3) no . .
C8 C9 3.033(4) no . .
C10 C14 3.034(5) no . .
C16 C19 3.084(7) no . .
C17 C18 3.174(5) no . .
S1 S1 3.5643(7) no . 2_655
F1 C6 3.485(3) no . 1_545
F12 C18 3.514(5) no . 2_655
F12 C19 3.595(6) no . 4_555
F12 C19 3.538(6) no . 4_565
O2 C16 3.444(4) no . 1_565
O3 C6 3.458(3) no . 1_545
O3 C15 3.548(5) no . 4_565
O3 C19 3.410(6) no . 4_555
O3 C22 3.289(4) no . 6_545
O11 C13 3.521(4) no . 1_545
O11 C22 3.413(3) no . 7_555
O20 C13 3.384(3) no . 7_565
O20 C15 3.532(4) no . 7_565
O21 C15 3.215(3) no . 7_565
O21 C22 3.405(3) no . 6_555
C4 C22 3.420(4) no . 6_555
C5 C13 3.571(4) no . 1_545
C6 F1 3.485(3) no . 1_565
C6 O3 3.458(3) no . 1_565
C13 O11 3.521(4) no . 1_565
C13 O20 3.384(3) no . 7_565
C13 C5 3.571(4) no . 1_565
C13 C13 3.540(3) no . 7_575
C15 O3 3.548(5) no . 4_564
C15 O20 3.532(4) no . 7_565
C15 O21 3.215(3) no . 7_565
C16 O2 3.444(4) no . 1_545
C18 F12 3.514(5) no . 2_655
C19 F12 3.595(6) no . 4_554
C19 F12 3.538(6) no . 4_564
C19 O3 3.410(6) no . 4_554
C22 O3 3.289(4) no . 6_555
C22 O11 3.413(3) no . 7_555
C22 O21 3.405(3) no . 6_545
C22 C4 3.420(4) no . 6_545
S1 H10A 2.7772 no . .
S1 H10B 2.8582 no . .
S1 H16A 3.4991 no . .
S1 H16B 2.7633 no . .
S1 H17A 2.9333 no . .
S1 H17B 2.6505 no . .
S1 H18B 2.9369 no . .
F1 H10A 2.6282 no . .
F1 H10B 3.2332 no . .
F1 H16B 2.9580 no . .
F12 H10A 2.2636 no . .
O2 H6 2.8551 no . .
O2 H10B 2.6168 no . .
O2 H17B 2.8859 no . .
O3 H5 2.3302 no . .
O11 H15A 2.5345 no . .
O11 H15B 2.7722 no . .
O20 H6 2.6395 no . .
O21 H5 2.6452 no . .
N23 H18A 3.3655 no . .
N23 H18B 2.7466 no . .
N23 H18C 2.7843 no . .
N23 H19A 2.6900 no . .
N23 H19B 2.6824 no . .
N23 H19C 3.3001 no . .
C1 H5 3.2609 no . .
C1 H13A 2.6399 no . .
C1 H13B 3.2021 no . .
C1 H13C 2.6255 no . .
C3 H6 3.3932 no . .
C3 H16B 3.3572 no . .
C4 H6 3.2661 no . .
C4 H22A 3.1964 no . .
C4 H22B 2.6209 no . .
C4 H22C 2.6117 no . .
C5 H22B 2.7069 no . .
C5 H22C 2.7909 no . .
C6 H10A 3.2499 no . .
C6 H10B 2.5693 no . .
C6 H13A 2.7657 no . .
C6 H13C 2.7802 no . .
C7 H6 3.2570 no . .
C7 H10A 2.7275 no . .
C7 H10B 3.3362 no . .
C8 H6 3.1129 no . .
C8 H10A 3.3978 no . .
C8 H10B 2.7659 no . .
C8 H15A 2.5335 no . .
C8 H15B 2.6672 no . .
C8 H15C 3.1693 no . .
C8 H17B 3.3445 no . .
C9 H5 3.2897 no . .
C10 H6 2.6166 no . .
C13 H6 2.5238 no . .
C14 H5 2.6108 no . .
C14 H10A 2.7230 no . .
C15 H6 3.4148 no . .
C15 H13C 3.4370 no . .
C15 H17B 3.5015 no . .
C16 H17A 2.7134 no . .
C16 H17B 3.3295 no . .
C16 H19A 3.3984 no . .
C16 H19B 2.7838 no . .
C17 H16A 2.6896 no . .
C17 H16B 3.3228 no . .
C17 H18B 3.4680 no . .
C17 H18C 2.9244 no . .
C18 H17A 2.8580 no . .
C18 H19B 3.4541 no . .
C19 H16A 2.7515 no . .
C19 H18C 3.5025 no . .
C22 H5 2.5184 no . .
H5 H22A 3.4852 no . .
H5 H22B 2.1987 no . .
H5 H22C 2.4244 no . .
H6 H10A 3.4616 no . .
H6 H10B 2.3454 no . .
H6 H13A 2.2962 no . .
H6 H13B 3.4968 no . .
H6 H13C 2.3409 no . .
H6 H15A 3.1772 no . .
H6 H15C 3.5641 no . .
H13C H15A 2.7578 no . .
H13C H15C 3.4148 no . .
H15B H17B 3.2139 no . .
H15B H19A 2.9256 no . .
H16A H17A 2.9725 no . .
H16A H17B 3.5906 no . .
H16A H18A 2.3641 no . .
H16A H18B 2.8583 no . .
H16A H18C 2.3539 no . .
H16A H19A 3.0083 no . .
H16A H19B 2.2166 no . .
H16B H18A 2.3332 no . .
H16B H18B 2.3856 no . .
H16B H18C 2.8572 no . .
H17A H18B 3.0893 no . .
H17A H18C 2.3804 no . .
H17A H19A 2.8114 no . .
H17A H19B 2.3159 no . .
H17A H19C 2.2897 no . .
H17B H19A 2.3096 no . .
H17B H19B 2.8114 no . .
H17B H19C 2.2960 no . .
H18C H19B 3.0595 no . .
S1 H16B 3.4438 no . 1_565
S1 H18A 3.4575 no . 1_565
S1 H18B 3.1422 no . 2_655
F1 H6 2.6585 no . 1_545
F1 H10B 2.9172 no . 1_545
F1 H13A 3.1128 no . 1_545
F1 H18B 3.5498 no . 2_655
F12 H16A 3.5647 no . 4_555
F12 H17A 3.5790 no . 2_655
F12 H18B 3.4565 no . 2_655
F12 H18C 2.7598 no . 2_655
F12 H19A 3.4670 no . 4_565
F12 H19B 2.8162 no . 4_555
F12 H19C 2.7889 no . 4_565
O2 H16A 3.2473 no . 1_565
O2 H16B 2.7323 no . 1_565
O3 H6 3.5748 no . 1_545
O3 H15B 3.0743 no . 4_565
O3 H15C 3.1129 no . 4_565
O3 H19A 2.8319 no . 4_555
O3 H19B 3.1156 no . 4_555
O3 H22A 2.4445 no . 6_545
O3 H22B 3.4165 no . 6_545
O11 H13A 3.0809 no . 1_545
O11 H13B 2.9219 no . 7_565
O11 H13C 3.2028 no . 1_545
O11 H15C 2.8706 no . 1_545
O11 H22A 3.1593 no . 7_555
O11 H22C 3.0062 no . 7_555
O20 H5 3.5838 no . 1_565
O20 H13B 3.5248 no . 7_565
O20 H13C 2.6427 no . 7_565
O20 H15A 2.5676 no . 7_565
O20 H22B 3.2120 no . 6_555
O20 H22C 2.9829 no . 1_565
O21 H5 3.0824 no . 6_555
O21 H13C 3.2317 no . 7_565
O21 H15A 2.7203 no . 7_565
O21 H15B 3.4590 no . 7_565
O21 H15C 2.9845 no . 7_565
O21 H22B 2.5955 no . 6_555
O21 H22C 3.4256 no . 6_555
C1 H13B 3.3860 no . 7_565
C1 H13C 3.0634 no . 7_565
C1 H15A 3.5635 no . 7_565
C1 H22B 3.1223 no . 6_555
C4 H13A 3.1484 no . 1_545
C4 H13B 3.5318 no . 1_545
C4 H13C 3.3905 no . 7_565
C4 H22A 3.4859 no . 6_555
C4 H22B 2.7439 no . 6_555
C4 H22C 3.5387 no . 6_555
C5 H13A 2.8240 no . 1_545
C5 H15B 3.4243 no . 4_565
C5 H22B 3.4279 no . 6_555
C7 H13A 2.9885 no . 1_545
C7 H19A 3.5804 no . 4_565
C9 H13A 3.4309 no . 1_545
C13 H13B 2.7575 no . 7_575
C13 H13C 3.1534 no . 7_565
C13 H15A 3.3706 no . 7_565
C13 H22C 3.2953 no . 1_565
C14 H15B 3.3241 no . 4_565
C14 H19A 3.5399 no . 4_565
C14 H19B 3.4052 no . 4_555
C14 H19C 3.3896 no . 4_565
C15 H16A 3.4618 no . 1_565
C15 H16B 3.4552 no . 1_565
C15 H22A 3.3523 no . 7_565
C15 H22C 3.5245 no . 7_555
C16 H15C 3.4539 no . 1_545
C16 H17B 2.9163 no . 1_545
C17 H16A 3.3344 no . 1_565
C17 H18A 3.1809 no . 1_565
C18 H17B 3.2017 no . 1_545
C18 H18B 3.5274 no . 2_655
C18 H19B 3.4756 no . 3_655
C19 H18C 3.4346 no . 3_655
C22 H5 3.1385 no . 6_555
C22 H15C 3.2551 no . 7_565
C22 H22B 3.4613 no . 6_545
C22 H22B 3.3438 no . 6_555
C22 H22C 3.5794 no . 6_555
H5 O20 3.5838 no . 1_545
H5 O21 3.0824 no . 6_545
H5 C22 3.1385 no . 6_545
H5 H13A 3.0891 no . 1_545
H5 H15B 3.0605 no . 4_565
H5 H22A 2.8915 no . 6_545
H5 H22B 2.9610 no . 6_545
H5 H22C 3.5642 no . 6_555
H6 F1 2.6585 no . 1_565
H6 O3 3.5748 no . 1_565
H10A H17A 3.5516 no . 2_655
H10A H18A 3.0739 no . 2_665
H10A H19C 2.8475 no . 4_565
H10B F1 2.9172 no . 1_565
H10B H16B 2.9593 no . 1_565
H10B H18A 3.2584 no . 2_665
H10B H18B 3.4018 no . 2_665
H13A F1 3.1128 no . 1_565
H13A O11 3.0809 no . 1_565
H13A C4 3.1484 no . 1_565
H13A C5 2.8240 no . 1_565
H13A C7 2.9885 no . 1_565
H13A C9 3.4309 no . 1_565
H13A H5 3.0891 no . 1_565
H13A H13B 2.7880 no . 7_575
H13A H22C 3.3165 no . 1_565
H13B O11 2.9219 no . 7_565
H13B O20 3.5248 no . 7_565
H13B C1 3.3860 no . 7_565
H13B C4 3.5318 no . 1_565
H13B C13 2.7575 no . 7_575
H13B H13A 2.7880 no . 7_575
H13B H13B 2.1434 no . 7_575
H13B H13C 3.3482 no . 7_565
H13B H13C 2.9282 no . 7_575
H13B H15A 3.1035 no . 7_565
H13B H22C 3.0122 no . 1_565
H13C O11 3.2028 no . 1_565
H13C O20 2.6427 no . 7_565
H13C O21 3.2317 no . 7_565
H13C C1 3.0634 no . 7_565
H13C C4 3.3905 no . 7_565
H13C C13 3.1534 no . 7_565
H13C H13B 3.3482 no . 7_565
H13C H13B 2.9282 no . 7_575
H13C H13C 2.8865 no . 7_565
H15A O20 2.5676 no . 7_565
H15A O21 2.7203 no . 7_565
H15A C1 3.5635 no . 7_565
H15A C13 3.3706 no . 7_565
H15A H13B 3.1035 no . 7_565
H15A H22A 3.4366 no . 7_565
H15A H22C 3.0436 no . 7_555
H15B O3 3.0743 no . 4_564
H15B O21 3.4590 no . 7_565
H15B C5 3.4243 no . 4_564
H15B C14 3.3241 no . 4_564
H15B H5 3.0605 no . 4_564
H15B H16A 3.5256 no . 1_565
H15B H22A 3.3153 no . 7_555
H15B H22A 3.4593 no . 7_565
H15B H22C 3.1182 no . 7_555
H15C O3 3.1129 no . 4_564
H15C O11 2.8706 no . 1_565
H15C O21 2.9845 no . 7_565
H15C C16 3.4539 no . 1_565
H15C C22 3.2551 no . 7_565
H15C H16A 3.0564 no . 1_565
H15C H16B 3.1513 no . 1_565
H15C H22A 2.6761 no . 7_565
H16A F12 3.5647 no . 4_554
H16A O2 3.2473 no . 1_545
H16A C15 3.4618 no . 1_545
H16A C17 3.3344 no . 1_545
H16A H15B 3.5256 no . 1_545
H16A H15C 3.0564 no . 1_545
H16A H17A 3.5959 no . 1_545
H16A H17B 2.3766 no . 1_545
H16B S1 3.4438 no . 1_545
H16B O2 2.7323 no . 1_545
H16B C15 3.4552 no . 1_545
H16B H10B 2.9593 no . 1_545
H16B H15C 3.1513 no . 1_545
H16B H17B 2.8220 no . 1_545
H16B H18B 3.2818 no . 2_655
H17A F12 3.5790 no . 2_655
H17A H10A 3.5516 no . 2_655
H17A H16A 3.5959 no . 1_565
H17A H18A 2.8442 no . 1_565
H17A H19C 2.9877 no . 3_665
H17B C16 2.9163 no . 1_565
H17B C18 3.2017 no . 1_565
H17B H16A 2.3766 no . 1_565
H17B H16B 2.8220 no . 1_565
H17B H18A 2.6359 no . 1_565
H18A S1 3.4575 no . 1_545
H18A C17 3.1809 no . 1_545
H18A H10A 3.0739 no . 2_645
H18A H10B 3.2584 no . 2_645
H18A H17A 2.8442 no . 1_545
H18A H17B 2.6359 no . 1_545
H18A H19B 3.3734 no . 3_655
H18A H19C 3.1352 no . 3_655
H18B S1 3.1422 no . 2_655
H18B F1 3.5498 no . 2_655
H18B F12 3.4565 no . 2_655
H18B C18 3.5274 no . 2_655
H18B H10B 3.4018 no . 2_645
H18B H16B 3.2818 no . 2_655
H18B H18B 2.7624 no . 2_655
H18C F12 2.7598 no . 2_655
H18C C19 3.4346 no . 3_655
H18C H19B 2.7140 no . 3_655
H18C H19C 3.2802 no . 3_655
H19A F12 3.4670 no . 4_564
H19A O3 2.8319 no . 4_554
H19A C7 3.5804 no . 4_564
H19A C14 3.5399 no . 4_564
H19A H22A 3.3236 no . 7_555
H19B F12 2.8162 no . 4_554
H19B O3 3.1156 no . 4_554
H19B C14 3.4052 no . 4_554
H19B C18 3.4756 no . 3_655
H19B H18A 3.3734 no . 3_655
H19B H18C 2.7140 no . 3_655
H19C F12 2.7889 no . 4_564
H19C C14 3.3896 no . 4_564
H19C H10A 2.8475 no . 4_564
H19C H17A 2.9877 no . 3_665
H19C H18A 3.1352 no . 3_655
H19C H18C 3.2802 no . 3_655
H22A O3 2.4445 no . 6_555
H22A O11 3.1593 no . 7_555
H22A C4 3.4859 no . 6_545
H22A C15 3.3523 no . 7_565
H22A H5 2.8915 no . 6_555
H22A H15A 3.4366 no . 7_565
H22A H15B 3.3153 no . 7_555
H22A H15B 3.4593 no . 7_565
H22A H15C 2.6761 no . 7_565
H22A H19A 3.3236 no . 7_555
H22B O3 3.4165 no . 6_555
H22B O20 3.2120 no . 6_545
H22B O21 2.5955 no . 6_545
H22B C1 3.1223 no . 6_545
H22B C4 2.7439 no . 6_545
H22B C5 3.4279 no . 6_545
H22B C22 3.3438 no . 6_545
H22B C22 3.4613 no . 6_555
H22B H5 2.9610 no . 6_555
H22B H22B 3.1076 no . 6_545
H22B H22B 3.1076 no . 6_555
H22B H22C 2.9198 no . 6_555
H22C O11 3.0062 no . 7_555
H22C O20 2.9829 no . 1_545
H22C O21 3.4256 no . 6_545
H22C C4 3.5387 no . 6_545
H22C C13 3.2953 no . 1_545
H22C C15 3.5245 no . 7_555
H22C C22 3.5794 no . 6_545
H22C H5 3.5642 no . 6_545
H22C H13A 3.3165 no . 1_545
H22C H13B 3.0122 no . 1_545
H22C H15A 3.0436 no . 7_555
H22C H15B 3.1182 no . 7_555
H22C H22B 2.9198 no . 6_545

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20150501saiSCF3-3
_database_code_depnum_ccdc_archive 'CCDC 1415531'
_audit_update_record             
;
2015-07-28 deposited with the CCDC.
2015-12-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H14 F4 O5 S'
_chemical_formula_moiety         'C14 H14 F4 O5 S'
_chemical_formula_weight         370.32
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.1328(3)
_cell_length_b                   19.0087(6)
_cell_length_c                   10.7270(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.6528(9)
_cell_angle_gamma                90.0000
_cell_volume                     1604.40(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13126
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.45
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760.00
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15522
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3656
_reflns_number_gt                3121
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1568
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3656
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.268
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.490
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.35401(5) 0.11812(2) 0.44050(4) 0.04194(18) Uani 1.0 4 d . . .
F1 F 0.44198(19) 0.23295(6) 0.99033(13) 0.0673(4) Uani 1.0 4 d . . .
F2 F 0.3415(2) 0.25494(6) 0.46997(16) 0.0767(5) Uani 1.0 4 d . . .
F3 F 0.2600(3) 0.21619(7) 0.27846(15) 0.0959(7) Uani 1.0 4 d . . .
F4 F 0.5267(3) 0.22214(8) 0.3792(2) 0.0951(6) Uani 1.0 4 d . . .
O1 O 0.34643(17) 0.21001(7) 0.78562(14) 0.0509(4) Uani 1.0 4 d . . .
O2 O 0.70540(16) 0.04417(6) 0.55170(13) 0.0439(3) Uani 1.0 4 d . . .
O3 O 0.78906(14) 0.14183(6) 0.66698(12) 0.0395(3) Uani 1.0 4 d . . .
O4 O 0.83893(16) -0.04840(6) 1.03144(12) 0.0439(3) Uani 1.0 4 d . . .
O5 O 0.83910(17) 0.04705(7) 1.20079(12) 0.0464(4) Uani 1.0 4 d . . .
C1 C 0.53441(19) 0.12638(8) 0.91979(16) 0.0340(4) Uani 1.0 4 d . . .
C2 C 0.53051(18) 0.07371(8) 0.82741(15) 0.0317(4) Uani 1.0 4 d . . .
C3 C 0.63417(19) 0.01459(8) 0.86485(15) 0.0324(4) Uani 1.0 4 d . . .
C4 C 0.73645(19) 0.00729(8) 0.98850(15) 0.0341(4) Uani 1.0 4 d . . .
C5 C 0.7365(2) 0.05987(9) 1.08138(15) 0.0365(4) Uani 1.0 4 d . . .
C6 C 0.6377(2) 0.11884(8) 1.04632(16) 0.0364(4) Uani 1.0 4 d . . .
C7 C 0.4321(3) 0.19063(8) 0.88618(18) 0.0411(4) Uani 1.0 4 d . . .
C8 C 0.42093(19) 0.07531(8) 0.69096(15) 0.0336(4) Uani 1.0 4 d . . .
C9 C 0.49616(19) 0.12240(7) 0.60204(15) 0.0316(4) Uani 1.0 4 d . . .
C10 C 0.3732(3) 0.20650(9) 0.3914(2) 0.0513(5) Uani 1.0 4 d . . .
C11 C 0.67386(19) 0.09745(7) 0.60121(15) 0.0301(3) Uani 1.0 4 d . . .
C12 C 0.9645(2) 0.12228(10) 0.68032(19) 0.0463(5) Uani 1.0 4 d . . .
C13 C 0.8463(3) -0.10239(10) 0.93926(19) 0.0492(5) Uani 1.0 4 d . . .
C14 C 0.8483(4) 0.09976(13) 1.29638(19) 0.0615(6) Uani 1.0 4 d . . .
H1A H 0.3065 0.0929 0.6914 0.0404 Uiso 1.0 4 calc R . .
H2B H 0.4081 0.0268 0.6561 0.0404 Uiso 1.0 4 calc R . .
H3 H 0.5023 0.1720 0.6338 0.0380 Uiso 1.0 4 calc R . .
H4A H 0.9869 0.1196 0.5949 0.0556 Uiso 1.0 4 calc R . .
H5B H 0.9863 0.0763 0.7227 0.0556 Uiso 1.0 4 calc R . .
H6C H 1.0391 0.1576 0.7324 0.0556 Uiso 1.0 4 calc R . .
H7 H 0.6342 -0.0215 0.8036 0.0389 Uiso 1.0 4 calc R . .
H8A H 0.8765 -0.0814 0.8646 0.0591 Uiso 1.0 4 calc R . .
H9B H 0.7352 -0.1253 0.9112 0.0591 Uiso 1.0 4 calc R . .
H10C H 0.9323 -0.1373 0.9790 0.0591 Uiso 1.0 4 calc R . .
H11C H 0.8914 0.1435 1.2682 0.0738 Uiso 1.0 4 calc R . .
H12A H 0.9251 0.0842 1.3775 0.0738 Uiso 1.0 4 calc R . .
H13B H 0.7348 0.1079 1.3093 0.0738 Uiso 1.0 4 calc R . .
H14 H 0.6389 0.1549 1.1079 0.0437 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C9 1.8255(15) yes . .
S1 C10 1.7792(19) yes . .
F1 C7 1.362(3) yes . .
F2 C10 1.317(3) yes . .
F3 C10 1.336(3) yes . .
F4 C10 1.321(3) yes . .
O1 C7 1.185(3) yes . .
O2 C11 1.201(2) yes . .
O3 C11 1.3239(18) yes . .
O3 C12 1.446(2) yes . .
O4 C4 1.3540(19) yes . .
O4 C13 1.437(3) yes . .
O5 C5 1.3624(19) yes . .
O5 C14 1.422(3) yes . .
C1 C2 1.403(3) yes . .
C1 C6 1.411(3) yes . .
C1 C7 1.471(3) yes . .
C2 C3 1.401(2) yes . .
C2 C8 1.509(2) yes . .
C3 C4 1.383(2) yes . .
C4 C5 1.411(3) yes . .
C5 C6 1.375(3) yes . .
C8 C9 1.543(3) yes . .
C9 C11 1.523(3) yes . .
C3 H7 0.950 no . .
C6 H14 0.950 no . .
C8 H1A 0.990 no . .
C8 H2B 0.990 no . .
C9 H3 1.000 no . .
C12 H4A 0.980 no . .
C12 H5B 0.980 no . .
C12 H6C 0.980 no . .
C13 H8A 0.980 no . .
C13 H9B 0.980 no . .
C13 H10C 0.980 no . .
C14 H11C 0.980 no . .
C14 H12A 0.980 no . .
C14 H13B 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C9 S1 C10 99.04(8) yes . . .
C11 O3 C12 115.88(14) yes . . .
C4 O4 C13 116.97(13) yes . . .
C5 O5 C14 117.38(15) yes . . .
C2 C1 C6 120.56(14) yes . . .
C2 C1 C7 120.60(14) yes . . .
C6 C1 C7 118.84(15) yes . . .
C1 C2 C3 117.73(13) yes . . .
C1 C2 C8 124.95(14) yes . . .
C3 C2 C8 117.32(14) yes . . .
C2 C3 C4 121.85(15) yes . . .
O4 C4 C3 125.02(15) yes . . .
O4 C4 C5 115.05(13) yes . . .
C3 C4 C5 119.91(14) yes . . .
O5 C5 C4 115.32(15) yes . . .
O5 C5 C6 125.43(16) yes . . .
C4 C5 C6 119.25(14) yes . . .
C1 C6 C5 120.68(15) yes . . .
F1 C7 O1 117.53(15) yes . . .
F1 C7 C1 112.14(14) yes . . .
O1 C7 C1 130.33(18) yes . . .
C2 C8 C9 112.46(13) yes . . .
S1 C9 C8 107.82(10) yes . . .
S1 C9 C11 110.77(12) yes . . .
C8 C9 C11 110.38(12) yes . . .
S1 C10 F2 115.14(17) yes . . .
S1 C10 F3 107.86(13) yes . . .
S1 C10 F4 113.42(14) yes . . .
F2 C10 F3 106.41(17) yes . . .
F2 C10 F4 104.39(17) yes . . .
F3 C10 F4 109.3(2) yes . . .
O2 C11 O3 124.85(15) yes . . .
O2 C11 C9 125.05(13) yes . . .
O3 C11 C9 110.06(13) yes . . .
C2 C3 H7 119.069 no . . .
C4 C3 H7 119.082 no . . .
C1 C6 H14 119.660 no . . .
C5 C6 H14 119.659 no . . .
C2 C8 H1A 109.109 no . . .
C2 C8 H2B 109.109 no . . .
C9 C8 H1A 109.102 no . . .
C9 C8 H2B 109.104 no . . .
H1A C8 H2B 107.848 no . . .
S1 C9 H3 109.277 no . . .
C8 C9 H3 109.288 no . . .
C11 C9 H3 109.283 no . . .
O3 C12 H4A 109.470 no . . .
O3 C12 H5B 109.475 no . . .
O3 C12 H6C 109.477 no . . .
H4A C12 H5B 109.472 no . . .
H4A C12 H6C 109.469 no . . .
H5B C12 H6C 109.466 no . . .
O4 C13 H8A 109.472 no . . .
O4 C13 H9B 109.474 no . . .
O4 C13 H10C 109.474 no . . .
H8A C13 H9B 109.466 no . . .
H8A C13 H10C 109.464 no . . .
H9B C13 H10C 109.476 no . . .
O5 C14 H11C 109.472 no . . .
O5 C14 H12A 109.470 no . . .
O5 C14 H13B 109.475 no . . .
H11C C14 H12A 109.471 no . . .
H11C C14 H13B 109.468 no . . .
H12A C14 H13B 109.472 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C9 S1 C10 F2 -53.96(15) no . . . .
C9 S1 C10 F3 -172.59(14) no . . . .
C9 S1 C10 F4 66.20(15) no . . . .
C10 S1 C9 C8 144.02(11) no . . . .
C10 S1 C9 C11 -95.11(11) no . . . .
C12 O3 C11 O2 -1.3(3) no . . . .
C12 O3 C11 C9 176.55(13) no . . . .
C13 O4 C4 C3 2.7(3) no . . . .
C13 O4 C4 C5 -178.44(14) no . . . .
C14 O5 C5 C4 177.68(16) no . . . .
C14 O5 C5 C6 -1.7(3) no . . . .
C2 C1 C6 C5 0.1(3) no . . . .
C6 C1 C2 C3 -1.0(3) no . . . .
C6 C1 C2 C8 177.99(14) no . . . .
C2 C1 C7 F1 175.22(14) no . . . .
C2 C1 C7 O1 -5.1(3) no . . . .
C7 C1 C2 C3 178.48(14) no . . . .
C7 C1 C2 C8 -2.5(3) no . . . .
C6 C1 C7 F1 -5.3(3) no . . . .
C6 C1 C7 O1 174.46(18) no . . . .
C7 C1 C6 C5 -179.42(15) no . . . .
C1 C2 C3 C4 0.5(3) no . . . .
C1 C2 C8 C9 79.5(2) no . . . .
C3 C2 C8 C9 -101.46(16) no . . . .
C8 C2 C3 C4 -178.55(13) no . . . .
C2 C3 C4 O4 179.67(15) no . . . .
C2 C3 C4 C5 0.9(3) no . . . .
O4 C4 C5 O5 -0.1(3) no . . . .
O4 C4 C5 C6 179.28(14) no . . . .
C3 C4 C5 O5 178.81(14) no . . . .
C3 C4 C5 C6 -1.8(3) no . . . .
O5 C5 C6 C1 -179.35(15) no . . . .
C4 C5 C6 C1 1.3(3) no . . . .
C2 C8 C9 S1 178.88(11) no . . . .
C2 C8 C9 C11 57.77(16) no . . . .
S1 C9 C11 O2 -48.61(18) no . . . .
S1 C9 C11 O3 133.58(10) no . . . .
C8 C9 C11 O2 70.73(19) no . . . .
C8 C9 C11 O3 -107.08(13) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 O2 3.1371(13) no . .
F1 C6 2.667(2) no . .
F2 O1 3.482(3) no . .
F2 C9 3.0058(19) no . .
F4 C9 3.110(3) no . .
F4 C11 3.359(3) no . .
O1 C2 2.969(2) no . .
O1 C8 2.875(2) no . .
O1 C9 3.057(3) no . .
O2 C3 3.594(3) no . .
O2 C8 3.112(3) no . .
O2 C12 2.660(2) no . .
O3 C2 3.300(3) no . .
O3 C8 3.319(2) no . .
O4 O5 2.5673(19) no . .
O4 C6 3.598(2) no . .
C1 C4 2.785(2) no . .
C1 C9 3.344(3) no . .
C2 C5 2.826(2) no . .
C2 C11 2.980(3) no . .
C3 C6 2.773(3) no . .
C3 C9 3.436(2) no . .
C3 C11 3.323(3) no . .
C3 C13 2.804(3) no . .
C6 C14 2.817(3) no . .
C7 C8 3.017(3) no . .
C7 C9 3.471(3) no . .
C10 C11 3.544(3) no . .
S1 O2 3.1269(13) no . 3_656
F1 F2 3.319(3) no . 4_555
F1 F4 3.394(3) no . 4_455
F1 O3 3.4634(19) no . 4_455
F1 C12 3.402(3) no . 4_455
F2 F1 3.319(3) no . 4_454
F2 C1 3.307(2) no . 4_454
F2 C6 3.141(3) no . 4_454
F2 C7 3.384(3) no . 4_454
F3 O3 2.9854(19) no . 4_454
F3 C13 3.140(3) no . 3_656
F4 F1 3.394(3) no . 4_554
F4 O1 3.279(3) no . 4_554
O1 F4 3.279(3) no . 4_455
O1 C12 3.454(3) no . 1_455
O2 S1 3.1269(13) no . 3_656
O2 C8 3.411(2) no . 3_656
O2 C14 3.403(3) no . 1_554
O3 F1 3.4634(19) no . 4_554
O3 F3 2.9854(19) no . 4_555
O4 O4 3.4057(19) no . 3_757
O4 C1 3.535(3) no . 3_657
O4 C4 3.599(2) no . 3_757
O4 C12 3.404(3) no . 3_757
O5 C8 3.532(3) no . 3_657
O5 C13 3.443(3) no . 3_757
C1 F2 3.307(2) no . 4_555
C1 O4 3.535(3) no . 3_657
C3 C5 3.507(3) no . 3_657
C4 O4 3.599(2) no . 3_757
C5 C3 3.507(3) no . 3_657
C5 C13 3.549(3) no . 3_757
C6 F2 3.141(3) no . 4_555
C7 F2 3.384(3) no . 4_555
C8 O2 3.411(2) no . 3_656
C8 O5 3.532(3) no . 3_657
C12 F1 3.402(3) no . 4_554
C12 O1 3.454(3) no . 1_655
C12 O4 3.404(3) no . 3_757
C13 F3 3.140(3) no . 3_656
C13 O5 3.443(3) no . 3_757
C13 C5 3.549(3) no . 3_757
C14 O2 3.403(3) no . 1_556
S1 H1A 2.8546 no . .
S1 H2B 2.8356 no . .
F1 H14 2.3102 no . .
F2 H3 2.4733 no . .
F4 H3 2.9457 no . .
O1 H1A 2.4324 no . .
O1 H3 2.4135 no . .
O2 H2B 2.9294 no . .
O2 H3 3.1856 no . .
O2 H4A 2.6417 no . .
O2 H5B 2.6150 no . .
O2 H7 3.1598 no . .
O3 H3 2.3402 no . .
O4 H7 2.6364 no . .
O5 H14 2.6502 no . .
C1 H1A 2.7469 no . .
C1 H2B 3.3415 no . .
C1 H3 3.1352 no . .
C1 H7 3.2594 no . .
C2 H3 2.7604 no . .
C2 H14 3.2969 no . .
C3 H1A 3.2048 no . .
C3 H2B 2.5230 no . .
C3 H8A 2.6855 no . .
C3 H9B 2.7913 no . .
C4 H8A 2.5821 no . .
C4 H9B 2.6533 no . .
C4 H10C 3.1910 no . .
C4 H14 3.2641 no . .
C5 H7 3.2726 no . .
C5 H11C 2.6181 no . .
C5 H12A 3.1929 no . .
C5 H13B 2.6131 no . .
C6 H11C 2.7671 no . .
C6 H13B 2.7386 no . .
C7 H1A 2.7893 no . .
C7 H3 2.9265 no . .
C7 H14 2.6316 no . .
C8 H7 2.6061 no . .
C9 H7 3.4908 no . .
C10 H3 2.6287 no . .
C11 H1A 3.3663 no . .
C11 H2B 2.7324 no . .
C11 H4A 2.5987 no . .
C11 H5B 2.5772 no . .
C11 H6C 3.1620 no . .
C11 H7 3.2065 no . .
C13 H7 2.4880 no . .
C14 H14 2.5185 no . .
H1A H3 2.3829 no . .
H1A H7 3.4138 no . .
H2B H3 2.8907 no . .
H2B H7 2.2923 no . .
H5B H8A 3.5759 no . .
H7 H8A 2.2260 no . .
H7 H9B 2.3296 no . .
H7 H10C 3.4582 no . .
H11C H14 2.3304 no . .
H12A H14 3.4902 no . .
H13B H14 2.2853 no . .
S1 H7 3.2196 no . 3_656
S1 H8A 3.4076 no . 3_656
S1 H12A 3.4418 no . 1_454
F1 H4A 3.0061 no . 4_455
F1 H6C 3.2642 no . 4_455
F1 H9B 2.8537 no . 3_657
F1 H11C 3.2962 no . 4_454
F2 H10C 2.7148 no . 2_656
F2 H14 3.0126 no . 4_454
F3 H3 3.1097 no . 4_454
F3 H6C 3.4231 no . 4_454
F3 H8A 3.0489 no . 3_656
F3 H9B 2.6766 no . 3_656
F3 H10C 3.1842 no . 3_656
F3 H11C 3.2771 no . 1_454
F4 H6C 2.7918 no . 4_454
F4 H10C 3.0507 no . 2_656
F4 H13B 2.9643 no . 1_554
F4 H14 3.5046 no . 1_554
O1 H4A 3.5579 no . 1_455
O1 H6C 2.6158 no . 1_455
O1 H11C 2.8201 no . 4_454
O1 H14 3.3838 no . 4_454
O2 H2B 2.5695 no . 3_656
O2 H12A 2.9920 no . 1_554
O2 H13B 2.9321 no . 1_554
O4 H1A 3.5683 no . 3_657
O4 H5B 2.7130 no . 3_757
O4 H6C 3.2313 no . 3_757
O4 H8A 3.3730 no . 3_757
O5 H1A 3.2418 no . 3_657
O5 H2B 3.1511 no . 3_657
O5 H5B 2.7569 no . 3_757
O5 H8A 2.6625 no . 3_757
O5 H10C 3.4545 no . 3_757
C1 H9B 3.1786 no . 3_657
C4 H8A 3.4444 no . 3_757
C5 H8A 3.0804 no . 3_757
C5 H10C 3.2751 no . 3_757
C6 H7 3.5646 no . 3_657
C6 H9B 3.1804 no . 3_657
C6 H10C 3.5930 no . 3_757
C7 H6C 3.2651 no . 1_455
C7 H9B 3.0996 no . 3_657
C7 H11C 3.3818 no . 4_454
C8 H4A 3.5198 no . 1_455
C10 H6C 3.5447 no . 4_454
C10 H9B 3.4996 no . 3_656
C10 H10C 3.4841 no . 2_656
C11 H2B 3.5658 no . 3_656
C11 H12A 3.5323 no . 1_554
C11 H13B 3.2974 no . 1_554
C12 H1A 2.8099 no . 1_655
C12 H10C 3.5478 no . 3_757
C12 H12A 3.2635 no . 1_554
C13 H5B 3.5706 no . 3_757
C13 H6C 3.5659 no . 3_757
C13 H11C 3.5377 no . 3_757
C14 H2B 3.3068 no . 3_657
C14 H4A 3.1370 no . 1_556
C14 H8A 3.1734 no . 3_757
H1A O4 3.5683 no . 3_657
H1A O5 3.2418 no . 3_657
H1A C12 2.8099 no . 1_455
H1A H4A 2.5928 no . 1_455
H1A H5B 2.7267 no . 1_455
H1A H6C 2.6306 no . 1_455
H2B O2 2.5695 no . 3_656
H2B O5 3.1511 no . 3_657
H2B C11 3.5658 no . 3_656
H2B C14 3.3068 no . 3_657
H2B H12A 3.3813 no . 3_657
H2B H13B 2.8742 no . 3_657
H3 F3 3.1097 no . 4_555
H4A F1 3.0061 no . 4_554
H4A O1 3.5579 no . 1_655
H4A C8 3.5198 no . 1_655
H4A C14 3.1370 no . 1_554
H4A H1A 2.5928 no . 1_655
H4A H11C 3.4229 no . 1_554
H4A H12A 2.3558 no . 1_554
H4A H13B 3.2343 no . 1_554
H5B O4 2.7130 no . 3_757
H5B O5 2.7569 no . 3_757
H5B C13 3.5706 no . 3_757
H5B H1A 2.7267 no . 1_655
H5B H10C 3.3085 no . 3_757
H5B H12A 3.3731 no . 3_757
H6C F1 3.2642 no . 4_554
H6C F3 3.4231 no . 4_555
H6C F4 2.7918 no . 4_555
H6C O1 2.6158 no . 1_655
H6C O4 3.2313 no . 3_757
H6C C7 3.2651 no . 1_655
H6C C10 3.5447 no . 4_555
H6C C13 3.5659 no . 3_757
H6C H1A 2.6306 no . 1_655
H6C H10C 3.0695 no . 3_757
H7 S1 3.2196 no . 3_656
H7 C6 3.5646 no . 3_657
H7 H13B 3.3658 no . 3_657
H8A S1 3.4076 no . 3_656
H8A F3 3.0489 no . 3_656
H8A O4 3.3730 no . 3_757
H8A O5 2.6625 no . 3_757
H8A C4 3.4444 no . 3_757
H8A C5 3.0804 no . 3_757
H8A C14 3.1734 no . 3_757
H8A H11C 2.8899 no . 3_757
H8A H12A 3.3873 no . 3_757
H9B F1 2.8537 no . 3_657
H9B F3 2.6766 no . 3_656
H9B C1 3.1786 no . 3_657
H9B C6 3.1804 no . 3_657
H9B C7 3.0996 no . 3_657
H9B C10 3.4996 no . 3_656
H9B H14 3.0493 no . 3_657
H10C F2 2.7148 no . 2_646
H10C F3 3.1842 no . 3_656
H10C F4 3.0507 no . 2_646
H10C O5 3.4545 no . 3_757
H10C C5 3.2751 no . 3_757
H10C C6 3.5930 no . 3_757
H10C C10 3.4841 no . 2_646
H10C C12 3.5478 no . 3_757
H10C H5B 3.3085 no . 3_757
H10C H6C 3.0695 no . 3_757
H10C H11C 3.3204 no . 3_757
H11C F1 3.2962 no . 4_555
H11C F3 3.2771 no . 1_656
H11C O1 2.8201 no . 4_555
H11C C7 3.3818 no . 4_555
H11C C13 3.5377 no . 3_757
H11C H4A 3.4229 no . 1_556
H11C H8A 2.8899 no . 3_757
H11C H10C 3.3204 no . 3_757
H12A S1 3.4418 no . 1_656
H12A O2 2.9920 no . 1_556
H12A C11 3.5323 no . 1_556
H12A C12 3.2635 no . 1_556
H12A H2B 3.3813 no . 3_657
H12A H4A 2.3558 no . 1_556
H12A H5B 3.3731 no . 3_757
H12A H8A 3.3873 no . 3_757
H13B F4 2.9643 no . 1_556
H13B O2 2.9321 no . 1_556
H13B C11 3.2974 no . 1_556
H13B H2B 2.8742 no . 3_657
H13B H4A 3.2343 no . 1_556
H13B H7 3.3658 no . 3_657
H14 F2 3.0126 no . 4_555
H14 F4 3.5046 no . 1_556
H14 O1 3.3838 no . 4_555
H14 H9B 3.0493 no . 3_657

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
