# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cu_14fg004_0m
_database_code_depnum_ccdc_archive 'CCDC 1577907'
_audit_update_record             
;
2017-10-03 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 F3 N O2 S'
_chemical_formula_weight         337.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.1745(5)
_cell_length_b                   10.1237(6)
_cell_length_c                   20.5314(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1699.10(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9745
_cell_measurement_theta_min      4.31
_cell_measurement_theta_max      74.57

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    2.026
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32217
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.31
_diffrn_reflns_theta_max         74.60
_reflns_number_total             3474
_reflns_number_gt                3356
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0439P)²+0.5049P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.050(15)
_refine_ls_number_reflns         3474
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.002
_chemical_absolute_configuration ad

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 0.21769(4) -0.06316(3) 0.251072(18) 0.01709(9) Uani 1 1 d . . .
F1 F 0.24696(13) -0.19147(9) 0.12129(5) 0.0255(2) Uani 1 1 d . . .
F2 F 0.41151(12) -0.04535(10) 0.08217(5) 0.0277(2) Uani 1 1 d . . .
F3 F 0.19126(14) -0.09658(11) 0.03059(5) 0.0291(2) Uani 1 1 d . . .
N1 N 0.23836(16) 0.04981(14) 0.19278(6) 0.0167(3) Uani 1 1 d . . .
O2 O 0.37126(15) -0.14380(12) 0.25452(6) 0.0267(3) Uani 1 1 d . . .
O1 O -0.42742(14) 0.13146(12) 0.17980(7) 0.0238(3) Uani 1 1 d . . .
C1 C 0.2218(2) -0.05138(18) 0.38064(8) 0.0265(4) Uani 1 1 d . . .
H14 H 0.2179 -0.0015 0.4215 0.040 Uiso 1 1 calc R . .
H15 H 0.3206 -0.1062 0.3798 0.040 Uiso 1 1 calc R . .
H1 H 0.1250 -0.1080 0.3774 0.040 Uiso 1 1 calc R . .
C2 C 0.2249(2) 0.04492(16) 0.32309(7) 0.0211(3) Uani 1 1 d . . .
C3 C 0.16058(19) 0.03390(16) 0.12850(7) 0.0166(3) Uani 1 1 d . . .
C4 C 0.17178(18) 0.16678(16) 0.09188(8) 0.0172(3) Uani 1 1 d . . .
C5 C 0.0991(2) 0.18006(17) 0.03073(8) 0.0205(3) Uani 1 1 d . . .
H4 H 0.0469 0.1060 0.0114 0.025 Uiso 1 1 calc R . .
C6 C 0.1017(2) 0.29977(18) -0.00232(8) 0.0231(3) Uani 1 1 d . . .
H7 H 0.0516 0.3068 -0.0439 0.028 Uiso 1 1 calc R . .
C7 C 0.1769(2) 0.40837(18) 0.02499(9) 0.0246(4) Uani 1 1 d . . .
H2 H 0.1793 0.4901 0.0023 0.030 Uiso 1 1 calc R . .
C8 C 0.3808(3) 0.1281(2) 0.32371(9) 0.0325(4) Uani 1 1 d . . .
H20 H 0.3746 0.1953 0.2895 0.049 Uiso 1 1 calc R . .
H19 H 0.4756 0.0710 0.3159 0.049 Uiso 1 1 calc R . .
H3 H 0.3923 0.1712 0.3662 0.049 Uiso 1 1 calc R . .
C9 C 0.2493(2) 0.39733(16) 0.08609(9) 0.0233(3) Uani 1 1 d . . .
H5 H 0.3010 0.4718 0.1053 0.028 Uiso 1 1 calc R . .
C10 C 0.2460(2) 0.27679(16) 0.11934(8) 0.0195(3) Uani 1 1 d . . .
H6 H 0.2951 0.2701 0.1612 0.023 Uiso 1 1 calc R . .
C11 C 0.2532(2) -0.07448(17) 0.09037(8) 0.0206(3) Uani 1 1 d . . .
C12 C -0.01912(19) -0.01162(16) 0.13518(8) 0.0187(3) Uani 1 1 d . . .
H8 H -0.0558 -0.0476 0.0928 0.022 Uiso 1 1 calc R . .
H9 H -0.0240 -0.0843 0.1674 0.022 Uiso 1 1 calc R . .
C13 C -0.1377(2) 0.09652(16) 0.15612(9) 0.0208(3) Uani 1 1 d . . .
H11 H -0.0880 0.1490 0.1917 0.025 Uiso 1 1 calc R . .
H10 H -0.1586 0.1565 0.1190 0.025 Uiso 1 1 calc R . .
C14 C -0.2988(2) 0.03772(17) 0.17945(9) 0.0240(3) Uani 1 1 d . . .
H12 H -0.3292 -0.0368 0.1507 0.029 Uiso 1 1 calc R . .
H13 H -0.2842 0.0024 0.2240 0.029 Uiso 1 1 calc R . .
C15 C 0.0709(3) 0.12892(18) 0.32227(9) 0.0298(4) Uani 1 1 d . . .
H18 H -0.0246 0.0721 0.3155 0.045 Uiso 1 1 calc R . .
H16 H 0.0780 0.1936 0.2869 0.045 Uiso 1 1 calc R . .
H17 H 0.0600 0.1752 0.3640 0.045 Uiso 1 1 calc R . .
H1N H 0.335(3) 0.080(2) 0.1927(10) 0.021(5) Uiso 1 1 d . . .
H1O H -0.400(3) 0.190(3) 0.2069(12) 0.041(7) 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
S1 O2 1.4991(12) . ?
S1 N1 1.6640(13) . ?
S1 C2 1.8403(16) . ?
F1 C11 1.3448(19) . ?
F2 C11 1.3382(19) . ?
F3 C11 1.3464(19) . ?
N1 C3 1.4738(19) . ?
N1 H1N 0.85(2) . ?
O1 C14 1.416(2) . ?
O1 H1O 0.84(3) . ?
C1 C2 1.532(2) . ?
C1 H14 0.9800 . ?
C1 H15 0.9800 . ?
C1 H1 0.9800 . ?
C2 C15 1.519(2) . ?
C2 C8 1.527(3) . ?
C3 C4 1.544(2) . ?
C3 C12 1.546(2) . ?
C3 C11 1.546(2) . ?
C4 C10 1.388(2) . ?
C4 C5 1.395(2) . ?
C5 C6 1.389(2) . ?
C5 H4 0.9500 . ?
C6 C7 1.379(3) . ?
C6 H7 0.9500 . ?
C7 C9 1.392(3) . ?
C7 H2 0.9500 . ?
C8 H20 0.9800 . ?
C8 H19 0.9800 . ?
C8 H3 0.9800 . ?
C9 C10 1.399(2) . ?
C9 H5 0.9500 . ?
C10 H6 0.9500 . ?
C12 C13 1.524(2) . ?
C12 H8 0.9900 . ?
C12 H9 0.9900 . ?
C13 C14 1.523(2) . ?
C13 H11 0.9900 . ?
C13 H10 0.9900 . ?
C14 H12 0.9900 . ?
C14 H13 0.9900 . ?
C15 H18 0.9800 . ?
C15 H16 0.9800 . ?
C15 H17 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 N1 108.86(7) . . ?
O2 S1 C2 105.00(8) . . ?
N1 S1 C2 99.55(7) . . ?
C3 N1 S1 121.68(11) . . ?
C3 N1 H1N 116.1(14) . . ?
S1 N1 H1N 110.2(14) . . ?
C14 O1 H1O 106.0(18) . . ?
C2 C1 H14 109.5 . . ?
C2 C1 H15 109.5 . . ?
H14 C1 H15 109.5 . . ?
C2 C1 H1 109.5 . . ?
H14 C1 H1 109.5 . . ?
H15 C1 H1 109.5 . . ?
C15 C2 C8 112.52(15) . . ?
C15 C2 C1 110.54(15) . . ?
C8 C2 C1 110.98(15) . . ?
C15 C2 S1 107.29(12) . . ?
C8 C2 S1 111.18(12) . . ?
C1 C2 S1 103.93(11) . . ?
N1 C3 C4 108.38(13) . . ?
N1 C3 C12 111.29(13) . . ?
C4 C3 C12 111.06(12) . . ?
N1 C3 C11 108.65(12) . . ?
C4 C3 C11 110.05(13) . . ?
C12 C3 C11 107.37(13) . . ?
C10 C4 C5 118.32(15) . . ?
C10 C4 C3 121.82(14) . . ?
C5 C4 C3 119.79(15) . . ?
C6 C5 C4 121.13(16) . . ?
C6 C5 H4 119.4 . . ?
C4 C5 H4 119.4 . . ?
C7 C6 C5 120.26(15) . . ?
C7 C6 H7 119.9 . . ?
C5 C6 H7 119.9 . . ?
C6 C7 C9 119.48(16) . . ?
C6 C7 H2 120.3 . . ?
C9 C7 H2 120.3 . . ?
C2 C8 H20 109.5 . . ?
C2 C8 H19 109.5 . . ?
H20 C8 H19 109.5 . . ?
C2 C8 H3 109.5 . . ?
H20 C8 H3 109.5 . . ?
H19 C8 H3 109.5 . . ?
C7 C9 C10 120.14(16) . . ?
C7 C9 H5 119.9 . . ?
C10 C9 H5 119.9 . . ?
C4 C10 C9 120.67(15) . . ?
C4 C10 H6 119.7 . . ?
C9 C10 H6 119.7 . . ?
F2 C11 F1 106.85(13) . . ?
F2 C11 F3 106.58(13) . . ?
F1 C11 F3 105.65(14) . . ?
F2 C11 C3 112.39(14) . . ?
F1 C11 C3 111.57(13) . . ?
F3 C11 C3 113.31(13) . . ?
C13 C12 C3 114.53(13) . . ?
C13 C12 H8 108.6 . . ?
C3 C12 H8 108.6 . . ?
C13 C12 H9 108.6 . . ?
C3 C12 H9 108.6 . . ?
H8 C12 H9 107.6 . . ?
C14 C13 C12 110.98(13) . . ?
C14 C13 H11 109.4 . . ?
C12 C13 H11 109.4 . . ?
C14 C13 H10 109.4 . . ?
C12 C13 H10 109.4 . . ?
H11 C13 H10 108.0 . . ?
O1 C14 C13 112.45(13) . . ?
O1 C14 H12 109.1 . . ?
C13 C14 H12 109.1 . . ?
O1 C14 H13 109.1 . . ?
C13 C14 H13 109.1 . . ?
H12 C14 H13 107.8 . . ?
C2 C15 H18 109.5 . . ?
C2 C15 H16 109.5 . . ?
H18 C15 H16 109.5 . . ?
C2 C15 H17 109.5 . . ?
H18 C15 H17 109.5 . . ?
H16 C15 H17 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 C3 102.50(13) . . . . ?
C2 S1 N1 C3 -147.93(13) . . . . ?
O2 S1 C2 C15 -179.72(11) . . . . ?
N1 S1 C2 C15 67.67(12) . . . . ?
O2 S1 C2 C8 56.85(14) . . . . ?
N1 S1 C2 C8 -55.76(13) . . . . ?
O2 S1 C2 C1 -62.60(13) . . . . ?
N1 S1 C2 C1 -175.21(12) . . . . ?
S1 N1 C3 C4 167.89(10) . . . . ?
S1 N1 C3 C12 45.48(17) . . . . ?
S1 N1 C3 C11 -72.54(15) . . . . ?
N1 C3 C4 C10 0.2(2) . . . . ?
C12 C3 C4 C10 122.78(16) . . . . ?
C11 C3 C4 C10 -118.46(16) . . . . ?
N1 C3 C4 C5 -176.67(13) . . . . ?
C12 C3 C4 C5 -54.13(19) . . . . ?
C11 C3 C4 C5 64.64(18) . . . . ?
C10 C4 C5 C6 0.5(2) . . . . ?
C3 C4 C5 C6 177.53(15) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C9 -0.4(3) . . . . ?
C6 C7 C9 C10 0.2(3) . . . . ?
C5 C4 C10 C9 -0.7(2) . . . . ?
C3 C4 C10 C9 -177.66(14) . . . . ?
C7 C9 C10 C4 0.4(3) . . . . ?
N1 C3 C11 F2 -59.05(16) . . . . ?
C4 C3 C11 F2 59.47(17) . . . . ?
C12 C3 C11 F2 -179.53(13) . . . . ?
N1 C3 C11 F1 60.95(17) . . . . ?
C4 C3 C11 F1 179.47(12) . . . . ?
C12 C3 C11 F1 -59.53(17) . . . . ?
N1 C3 C11 F3 -179.95(13) . . . . ?
C4 C3 C11 F3 -61.43(17) . . . . ?
C12 C3 C11 F3 59.57(17) . . . . ?
N1 C3 C12 C13 75.82(17) . . . . ?
C4 C3 C12 C13 -45.02(19) . . . . ?
C11 C3 C12 C13 -165.39(13) . . . . ?
C3 C12 C13 C14 -164.34(14) . . . . ?
C12 C13 C14 O1 -161.45(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H14 F3 0.98 2.56 3.497(2) 160.0 4
C12 H9 S1 0.99 2.63 3.1116(17) 110.2 .
C14 H12 F2 0.99 2.55 3.210(2) 124.4 1_455

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        74.60
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_cu_15fg012_0m
_database_code_depnum_ccdc_archive 'CCDC 1577911'
_audit_update_record             
;
2017-10-03 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H22 F3 N O3 S'
_chemical_formula_weight         317.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.535(5)
_cell_length_b                   10.972(5)
_cell_length_c                   9.930(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 99.961(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     808.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9835
_cell_measurement_theta_min      4.03
_cell_measurement_theta_max      72.21

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    2.138
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26501
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.52
_diffrn_reflns_theta_max         72.20
_reflns_number_total             3182
_reflns_number_gt                3128
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0396P)²+0.0824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.047(11)
_refine_ls_number_reflns         3182
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_chemical_absolute_configuration ad

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 0.17076(4) 0.10737(3) 0.26662(3) 0.02262(8) Uani 1 1 d . . .
F2 F 0.23829(12) 0.49985(8) 0.32489(9) 0.0319(2) Uani 1 1 d . . .
F3 F -0.04244(13) 0.53326(8) 0.24652(10) 0.0361(2) Uani 1 1 d . . .
F1 F 0.03489(14) 0.40597(9) 0.41153(9) 0.0375(2) Uani 1 1 d . . .
O2 O 0.44979(13) 0.38751(9) 0.11937(11) 0.0269(2) Uani 1 1 d . . .
O3 O 0.31832(13) 0.56302(9) 0.04147(10) 0.0246(2) Uani 1 1 d . . .
O1 O 0.19909(14) 0.04043(9) 0.14163(11) 0.0287(2) Uani 1 1 d . . .
N1 N 0.21454(16) 0.25518(10) 0.25391(12) 0.0214(2) Uani 1 1 d . . .
C2 C 0.12436(17) 0.39632(12) 0.05509(14) 0.0200(3) Uani 1 1 d . . .
C4 C 0.0760(2) 0.44551(13) 0.29319(15) 0.0263(3) Uani 1 1 d . . .
C3 C 0.31536(19) 0.44613(12) 0.07739(13) 0.0206(3) Uani 1 1 d . . .
C5 C -0.11339(19) 0.28715(13) 0.16263(17) 0.0282(3) Uani 1 1 d . . .
H5A H -0.1170 0.2195 0.1009 0.042 Uiso 1 1 calc R . .
H5B H -0.1981 0.3480 0.1230 0.042 Uiso 1 1 calc R . .
H5C H -0.1442 0.2597 0.2475 0.042 Uiso 1 1 calc R . .
C1 C 0.07658(18) 0.34170(12) 0.18892(14) 0.0207(3) Uani 1 1 d . . .
C8 C 0.49620(19) 0.61685(15) 0.05588(14) 0.0295(3) Uani 1 1 d . . .
H8A H 0.5522 0.6155 0.1504 0.044 Uiso 1 1 calc R . .
H8B H 0.4861 0.6996 0.0240 0.044 Uiso 1 1 calc R . .
H8C H 0.5682 0.5711 0.0029 0.044 Uiso 1 1 calc R . .
C9 C 0.3686(2) 0.07050(13) 0.39820(14) 0.0255(3) Uani 1 1 d . . .
C12 C 0.54249(17) 0.10826(17) 0.35169(13) 0.0275(3) Uani 1 1 d . . .
H12A H 0.5526 0.1955 0.3540 0.041 Uiso 1 1 calc R . .
H12B H 0.5414 0.0799 0.2601 0.041 Uiso 1 1 calc R . .
H12C H 0.6432 0.0732 0.4116 0.041 Uiso 1 1 calc R . .
C6 C 0.1049(2) 0.30177(14) -0.06194(14) 0.0253(3) Uani 1 1 d . . .
H6A H 0.1707 0.2287 -0.0289 0.030 Uiso 1 1 calc R . .
H6B H -0.0212 0.2799 -0.0876 0.030 Uiso 1 1 calc R . .
C11 C 0.3431(2) 0.13331(15) 0.53047(15) 0.0330(3) Uani 1 1 d . . .
H11A H 0.2283 0.1109 0.5525 0.050 Uiso 1 1 calc R . .
H11B H 0.3477 0.2201 0.5190 0.050 Uiso 1 1 calc R . .
H11C H 0.4372 0.1085 0.6032 0.050 Uiso 1 1 calc R . .
C7 C 0.1740(2) 0.34791(15) -0.18792(15) 0.0324(3) Uani 1 1 d . . .
H7A H 0.1157 0.4235 -0.2173 0.049 Uiso 1 1 calc R . .
H7B H 0.1481 0.2888 -0.2600 0.049 Uiso 1 1 calc R . .
H7C H 0.3018 0.3605 -0.1659 0.049 Uiso 1 1 calc R . .
C10 C 0.3595(2) -0.06781(15) 0.41224(18) 0.0372(4) Uani 1 1 d . . .
H10A H 0.4515 -0.0944 0.4856 0.056 Uiso 1 1 calc R . .
H10B H 0.3779 -0.1055 0.3285 0.056 Uiso 1 1 calc R . .
H10C H 0.2434 -0.0906 0.4314 0.056 Uiso 1 1 calc R . .
H1N H 0.320(3) 0.2687(19) 0.2304(18) 0.028(5) Uiso 1 1 d . . .
H2 H 0.044(2) 0.4610(15) 0.0264(16) 0.014(4) 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
S1 O1 1.4889(12) . ?
S1 N1 1.6642(14) . ?
S1 C9 1.8490(17) . ?
F2 C4 1.3479(19) . ?
F3 C4 1.3398(18) . ?
F1 C4 1.3383(18) . ?
O2 C3 1.2114(18) . ?
O3 C3 1.3324(18) . ?
O3 C8 1.4489(18) . ?
N1 C1 1.4718(18) . ?
C2 C3 1.519(2) . ?
C2 C6 1.546(2) . ?
C2 C1 1.5558(19) . ?
C4 C1 1.5398(19) . ?
C5 C1 1.532(2) . ?
C9 C12 1.520(2) . ?
C9 C11 1.525(2) . ?
C9 C10 1.527(2) . ?
C6 C7 1.523(2) . ?

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 N1 111.02(6) . . ?
O1 S1 C9 105.48(7) . . ?
N1 S1 C9 96.93(6) . . ?
C3 O3 C8 115.08(11) . . ?
C1 N1 S1 121.84(10) . . ?
C3 C2 C6 108.38(11) . . ?
C3 C2 C1 111.55(10) . . ?
C6 C2 C1 112.19(12) . . ?
F3 C4 F1 107.17(12) . . ?
F3 C4 F2 106.62(12) . . ?
F1 C4 F2 106.07(12) . . ?
F3 C4 C1 112.22(12) . . ?
F1 C4 C1 112.26(12) . . ?
F2 C4 C1 112.10(11) . . ?
O2 C3 O3 123.47(13) . . ?
O2 C3 C2 125.01(13) . . ?
O3 C3 C2 111.50(11) . . ?
N1 C1 C5 113.02(12) . . ?
N1 C1 C4 105.44(11) . . ?
C5 C1 C4 107.00(12) . . ?
N1 C1 C2 111.89(11) . . ?
C5 C1 C2 110.64(11) . . ?
C4 C1 C2 108.51(11) . . ?
C12 C9 C11 112.47(13) . . ?
C12 C9 C10 110.69(14) . . ?
C11 C9 C10 110.88(13) . . ?
C12 C9 S1 110.95(10) . . ?
C11 C9 S1 107.67(11) . . ?
C10 C9 S1 103.81(11) . . ?
C7 C6 C2 113.15(13) . . ?

_diffrn_measured_fraction_theta_max 1.001
_diffrn_reflns_theta_full        72.20
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_cu_14fg005bis_0m
_database_code_depnum_ccdc_archive 'CCDC 1577908'
_audit_update_record             
;
2017-10-03 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H18 F3 N O S'
_chemical_formula_weight         257.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   P3(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   9.6709(5)
_cell_length_b                   9.6709(5)
_cell_length_c                   12.3901(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     1003.55(9)
_cell_formula_units_Z            3
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    8873
_cell_measurement_theta_min      5.28
_cell_measurement_theta_max      72.04

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    2.347
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10966
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.28
_diffrn_reflns_theta_max         72.04
_reflns_number_total             2596
_reflns_number_gt                2500
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0365P)²+0.1132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.048(14)
_refine_ls_number_reflns         2596
_refine_ls_number_parameters     153
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0686
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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 0.29705(5) 0.83703(5) 0.29781(3) 0.02506(10) Uani 1 1 d . . .
F1 F -0.02744(18) 0.8836(2) 0.02265(14) 0.0624(4) Uani 1 1 d . . .
F2 F 0.15838(16) 1.04271(15) 0.13061(11) 0.0469(3) Uani 1 1 d . . .
F3 F 0.21893(17) 0.96409(17) -0.01481(10) 0.0511(3) Uani 1 1 d . . .
O1 O 0.28205(17) 0.68521(17) 0.33862(10) 0.0381(3) Uani 1 1 d . . .
N1 N 0.26164(16) 0.82436(17) 0.16757(11) 0.0241(3) Uani 1 1 d . . .
C1 C 0.5377(3) 1.1327(2) 0.2437(3) 0.0537(7) Uani 1 1 d . . .
H14 H 0.6492 1.2171 0.2526 0.081 Uiso 1 1 calc R . .
H1 H 0.4674 1.1657 0.2779 0.081 Uiso 1 1 calc R . .
H13 H 0.5124 1.1138 0.1666 0.081 Uiso 1 1 calc R . .
C2 C 0.5132(2) 0.9809(2) 0.29604(15) 0.0341(4) Uani 1 1 d . . .
C3 C 0.1002(2) 0.7725(2) 0.12635(14) 0.0279(4) Uani 1 1 d . . .
C4 C 0.0522(2) 0.6347(2) 0.04518(14) 0.0337(4) Uani 1 1 d . . .
H9 H -0.0478 0.6126 0.0085 0.040 Uiso 1 1 calc R . .
H8 H 0.1365 0.6685 -0.0104 0.040 Uiso 1 1 calc R . .
C5 C 0.0278(2) 0.4853(2) 0.09699(16) 0.0388(4) Uani 1 1 d . . .
H7 H 0.1065 0.4936 0.1466 0.047 Uiso 1 1 calc R . .
C6 C -0.0956(3) 0.3423(3) 0.0787(2) 0.0531(6) Uani 1 1 d . . .
H2 H -0.1765 0.3297 0.0296 0.064 Uiso 1 1 calc R . .
H6 H -0.1036 0.2518 0.1147 0.064 Uiso 1 1 calc R . .
C7 C 0.5569(3) 1.0054(4) 0.4164(2) 0.0637(8) Uani 1 1 d . . .
H19 H 0.6705 1.0842 0.4244 0.096 Uiso 1 1 calc R . .
H18 H 0.5351 0.9038 0.4484 0.096 Uiso 1 1 calc R . .
H3 H 0.4928 1.0439 0.4532 0.096 Uiso 1 1 calc R . .
C8 C -0.0252(2) 0.7250(2) 0.21499(16) 0.0359(4) Uani 1 1 d . . .
H10 H -0.0301 0.6370 0.2574 0.054 Uiso 1 1 calc R . .
H11 H -0.1297 0.6906 0.1822 0.054 Uiso 1 1 calc R . .
H12 H 0.0037 0.8167 0.2623 0.054 Uiso 1 1 calc R . .
C9 C 0.1133(2) 0.9165(3) 0.06593(17) 0.0394(4) Uani 1 1 d . . .
C10 C 0.6040(2) 0.9118(2) 0.23868(15) 0.0322(4) Uani 1 1 d . . .
H15 H 0.5818 0.9050 0.1611 0.048 Uiso 1 1 calc R . .
H16 H 0.5699 0.8049 0.2670 0.048 Uiso 1 1 calc R . .
H17 H 0.7188 0.9810 0.2510 0.048 Uiso 1 1 calc R . .
H1N H 0.314(3) 0.796(3) 0.130(2) 0.032(6) 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
S1 O1 1.4898(14) . ?
S1 N1 1.6415(14) . ?
S1 C2 1.843(2) . ?
F1 C9 1.344(2) . ?
F2 C9 1.338(3) . ?
F3 C9 1.337(3) . ?
N1 C3 1.472(2) . ?
N1 H1N 0.83(2) . ?
C1 C2 1.512(3) . ?
C1 H14 0.9800 . ?
C1 H1 0.9800 . ?
C1 H13 0.9800 . ?
C2 C10 1.519(3) . ?
C2 C7 1.535(3) . ?
C3 C8 1.527(2) . ?
C3 C9 1.530(3) . ?
C3 C4 1.544(2) . ?
C4 C5 1.488(3) . ?
C4 H9 0.9900 . ?
C4 H8 0.9900 . ?
C5 C6 1.318(3) . ?
C5 H7 0.9500 . ?
C6 H2 0.9500 . ?
C6 H6 0.9500 . ?
C7 H19 0.9800 . ?
C7 H18 0.9800 . ?
C7 H3 0.9800 . ?
C8 H10 0.9800 . ?
C8 H11 0.9800 . ?
C8 H12 0.9800 . ?
C10 H15 0.9800 . ?
C10 H16 0.9800 . ?
C10 H17 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 N1 110.26(8) . . ?
O1 S1 C2 105.22(9) . . ?
N1 S1 C2 99.22(8) . . ?
C3 N1 S1 120.85(11) . . ?
C3 N1 H1N 114.5(16) . . ?
S1 N1 H1N 115.9(16) . . ?
C2 C1 H14 109.5 . . ?
C2 C1 H1 109.5 . . ?
H14 C1 H1 109.5 . . ?
C2 C1 H13 109.5 . . ?
H14 C1 H13 109.5 . . ?
H1 C1 H13 109.5 . . ?
C1 C2 C10 112.46(18) . . ?
C1 C2 C7 111.7(2) . . ?
C10 C2 C7 110.35(17) . . ?
C1 C2 S1 107.80(13) . . ?
C10 C2 S1 111.13(13) . . ?
C7 C2 S1 103.03(15) . . ?
N1 C3 C8 113.60(14) . . ?
N1 C3 C9 105.61(14) . . ?
C8 C3 C9 108.53(16) . . ?
N1 C3 C4 109.28(14) . . ?
C8 C3 C4 110.95(15) . . ?
C9 C3 C4 108.63(15) . . ?
C5 C4 C3 112.97(15) . . ?
C5 C4 H9 109.0 . . ?
C3 C4 H9 109.0 . . ?
C5 C4 H8 109.0 . . ?
C3 C4 H8 109.0 . . ?
H9 C4 H8 107.8 . . ?
C6 C5 C4 124.4(2) . . ?
C6 C5 H7 117.8 . . ?
C4 C5 H7 117.8 . . ?
C5 C6 H2 120.0 . . ?
C5 C6 H6 120.0 . . ?
H2 C6 H6 120.0 . . ?
C2 C7 H19 109.5 . . ?
C2 C7 H18 109.5 . . ?
H19 C7 H18 109.5 . . ?
C2 C7 H3 109.5 . . ?
H19 C7 H3 109.5 . . ?
H18 C7 H3 109.5 . . ?
C3 C8 H10 109.5 . . ?
C3 C8 H11 109.5 . . ?
H10 C8 H11 109.5 . . ?
C3 C8 H12 109.5 . . ?
H10 C8 H12 109.5 . . ?
H11 C8 H12 109.5 . . ?
F3 C9 F2 106.86(18) . . ?
F3 C9 F1 106.99(18) . . ?
F2 C9 F1 106.58(17) . . ?
F3 C9 C3 112.34(16) . . ?
F2 C9 C3 112.22(16) . . ?
F1 C9 C3 111.49(17) . . ?
C2 C10 H15 109.5 . . ?
C2 C10 H16 109.5 . . ?
H15 C10 H16 109.5 . . ?
C2 C10 H17 109.5 . . ?
H15 C10 H17 109.5 . . ?
H16 C10 H17 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 C3 92.88(14) . . . . ?
C2 S1 N1 C3 -157.03(14) . . . . ?
O1 S1 C2 C1 173.87(15) . . . . ?
N1 S1 C2 C1 59.81(15) . . . . ?
O1 S1 C2 C10 50.20(15) . . . . ?
N1 S1 C2 C10 -63.86(15) . . . . ?
O1 S1 C2 C7 -67.97(16) . . . . ?
N1 S1 C2 C7 177.97(15) . . . . ?
S1 N1 C3 C8 -3.3(2) . . . . ?
S1 N1 C3 C9 115.50(14) . . . . ?
S1 N1 C3 C4 -127.81(14) . . . . ?
N1 C3 C4 C5 68.26(19) . . . . ?
C8 C3 C4 C5 -57.8(2) . . . . ?
C9 C3 C4 C5 -176.98(15) . . . . ?
C3 C4 C5 C6 133.3(2) . . . . ?
N1 C3 C9 F3 59.1(2) . . . . ?
C8 C3 C9 F3 -178.79(16) . . . . ?
C4 C3 C9 F3 -58.1(2) . . . . ?
N1 C3 C9 F2 -61.38(19) . . . . ?
C8 C3 C9 F2 60.8(2) . . . . ?
C4 C3 C9 F2 -178.51(16) . . . . ?
N1 C3 C9 F1 179.15(16) . . . . ?
C8 C3 C9 F1 -58.7(2) . . . . ?
C4 C3 C9 F1 62.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.83(2) 2.09(3) 2.8955(19) 165(2) 3_564
C4 H8 O1 0.99 2.38 3.111(2) 129.7 3_564
C8 H12 F1 0.98 2.57 3.536(2) 168.8 2_675
C10 H15 S1 0.98 3.02 3.8413(19) 142.0 3_564
C10 H15 O1 0.98 2.62 3.465(2) 144.7 3_564

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        72.04
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_cu_15fg015_0m
_database_code_depnum_ccdc_archive 'CCDC 1577912'
_audit_update_record             
;
2017-10-03 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H44 F6 N2 O2 S2'
_chemical_formula_weight         546.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.071(5)
_cell_length_b                   16.862(5)
_cell_length_c                   19.003(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2907(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9935
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      72.31

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    2.187
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            48644
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         72.44
_reflns_number_total             5748
_reflns_number_gt                5551
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0365P)²+0.2711P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(9)
_refine_ls_number_reflns         5748
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0601
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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 0.98299(3) 0.313858(17) 0.128895(15) 0.01834(7) Uani 1 1 d . . .
S1' S 0.78585(4) 0.580858(18) 0.224508(16) 0.02018(7) Uani 1 1 d . . .
F3' F 0.66065(10) 0.82055(6) 0.20160(5) 0.0392(2) Uani 1 1 d . . .
F1' F 0.53671(10) 0.71364(6) 0.18407(5) 0.0380(2) Uani 1 1 d . . .
O1 O 1.00627(11) 0.29005(5) 0.20387(5) 0.0261(2) Uani 1 1 d . . .
F2 F 1.06269(11) 0.52264(6) 0.00870(5) 0.0403(2) Uani 1 1 d . . .
F1 F 1.06681(11) 0.39989(6) -0.02252(5) 0.0417(2) Uani 1 1 d . . .
F2' F 0.58425(11) 0.79118(6) 0.09724(6) 0.0468(3) Uani 1 1 d . . .
O1' O 0.92053(11) 0.53216(6) 0.21137(5) 0.0266(2) Uani 1 1 d . . .
F3 F 1.26587(11) 0.46806(7) -0.02497(5) 0.0440(2) Uani 1 1 d . . .
N1 N 1.02617(12) 0.40805(6) 0.11706(6) 0.0185(2) Uani 1 1 d . . .
C2 C 1.23141(15) 0.50114(7) 0.13311(7) 0.0205(3) Uani 1 1 d . . .
C8 C 0.78062(14) 0.31854(8) 0.11821(6) 0.0207(2) Uani 1 1 d . . .
N1' N 0.81958(13) 0.67549(7) 0.21079(6) 0.0215(2) Uani 1 1 d . . .
C1 C 1.17244(14) 0.43037(8) 0.08899(7) 0.0200(3) Uani 1 1 d . . .
C11 C 0.71159(16) 0.37383(9) 0.17187(8) 0.0285(3) Uani 1 1 d . . .
H11A H 0.7372 0.4276 0.1608 0.043 Uiso 1 1 calc R . .
H11B H 0.7475 0.3609 0.2180 0.043 Uiso 1 1 calc R . .
H11C H 0.6063 0.3680 0.1708 0.043 Uiso 1 1 calc R . .
C10' C 0.91444(17) 0.59525(9) 0.35595(7) 0.0291(3) Uani 1 1 d . . .
H10A H 0.9495 0.6472 0.3439 0.044 Uiso 1 1 calc R . .
H10B H 0.9836 0.5562 0.3397 0.044 Uiso 1 1 calc R . .
H10C H 0.9042 0.5912 0.4061 0.044 Uiso 1 1 calc R . .
C11' C 0.65259(17) 0.64424(10) 0.34129(8) 0.0307(3) Uani 1 1 d . . .
H11D H 0.6289 0.6393 0.3903 0.046 Uiso 1 1 calc R . .
H11E H 0.5649 0.6371 0.3137 0.046 Uiso 1 1 calc R . .
H11F H 0.6929 0.6959 0.3325 0.046 Uiso 1 1 calc R . .
C3' C 1.05522(17) 0.72303(9) 0.10992(8) 0.0283(3) Uani 1 1 d . . .
H3'1 H 1.0563 0.6757 0.1389 0.034 Uiso 1 1 calc R . .
H3'2 H 1.0518 0.7063 0.0611 0.034 Uiso 1 1 calc R . .
C5' C 0.64239(18) 0.76045(9) 0.15641(8) 0.0322(3) Uani 1 1 d . . .
C3 C 1.26716(16) 0.47482(9) 0.20843(7) 0.0273(3) Uani 1 1 d . . .
H3A H 1.1901 0.4396 0.2250 0.033 Uiso 1 1 calc R . .
H3B H 1.3590 0.4454 0.2083 0.033 Uiso 1 1 calc R . .
C8' C 0.76561(16) 0.58116(8) 0.32123(7) 0.0244(3) Uani 1 1 d . . .
C7 C 1.36395(17) 0.54378(9) 0.10036(8) 0.0317(3) Uani 1 1 d . . .
H7A H 1.3973 0.5848 0.1316 0.048 Uiso 1 1 calc R . .
H7B H 1.3354 0.5669 0.0562 0.048 Uiso 1 1 calc R . .
H7C H 1.4422 0.5064 0.0927 0.048 Uiso 1 1 calc R . .
C6' C 0.75631(18) 0.65462(9) 0.08424(7) 0.0316(3) Uani 1 1 d . . .
H6'1 H 0.8386 0.6191 0.0802 0.047 Uiso 1 1 calc R . .
H6'2 H 0.7432 0.6825 0.0407 0.047 Uiso 1 1 calc R . .
H6'3 H 0.6688 0.6249 0.0948 0.047 Uiso 1 1 calc R . .
C5 C 1.14211(17) 0.45608(10) 0.01252(8) 0.0307(3) Uani 1 1 d . . .
C7' C 0.8859(2) 0.83129(10) 0.06793(9) 0.0375(4) Uani 1 1 d . . .
H7'1 H 0.9738 0.8613 0.0587 0.056 Uiso 1 1 calc R . .
H7'2 H 0.8085 0.8665 0.0824 0.056 Uiso 1 1 calc R . .
H7'3 H 0.8566 0.8038 0.0260 0.056 Uiso 1 1 calc R . .
C9' C 0.7081(2) 0.49831(9) 0.33805(8) 0.0390(4) Uani 1 1 d . . .
H9'1 H 0.7793 0.4595 0.3234 0.058 Uiso 1 1 calc R . .
H9'2 H 0.6171 0.4895 0.3135 0.058 Uiso 1 1 calc R . .
H9'3 H 0.6918 0.4937 0.3878 0.058 Uiso 1 1 calc R . .
C1' C 0.78553(16) 0.71423(8) 0.14342(7) 0.0239(3) Uani 1 1 d . . .
C6 C 1.28073(17) 0.36112(8) 0.08716(9) 0.0310(3) Uani 1 1 d . . .
H6A H 1.2892 0.3386 0.1334 0.046 Uiso 1 1 calc R . .
H6B H 1.3755 0.3797 0.0720 0.046 Uiso 1 1 calc R . .
H6C H 1.2456 0.3215 0.0550 0.046 Uiso 1 1 calc R . .
C9 C 0.73138(17) 0.23299(8) 0.13105(9) 0.0329(3) Uani 1 1 d . . .
H9A H 0.7520 0.2185 0.1789 0.049 Uiso 1 1 calc R . .
H9B H 0.7838 0.1982 0.0999 0.049 Uiso 1 1 calc R . .
H9C H 0.6274 0.2285 0.1225 0.049 Uiso 1 1 calc R . .
C2' C 0.91624(16) 0.77106(8) 0.12662(7) 0.0240(3) Uani 1 1 d . . .
C10 C 0.74903(17) 0.34338(10) 0.04276(8) 0.0311(3) Uani 1 1 d . . .
H10D H 0.6455 0.3380 0.0334 0.047 Uiso 1 1 calc R . .
H10E H 0.8036 0.3101 0.0111 0.047 Uiso 1 1 calc R . .
H10F H 0.7780 0.3976 0.0362 0.047 Uiso 1 1 calc R . .
C4' C 1.19681(18) 0.76932(10) 0.12242(9) 0.0360(3) Uani 1 1 d . . .
H4'1 H 1.1952 0.8171 0.0950 0.054 Uiso 1 1 calc R . .
H4'2 H 1.2798 0.7375 0.1087 0.054 Uiso 1 1 calc R . .
H4'3 H 1.2048 0.7825 0.1714 0.054 Uiso 1 1 calc R . .
C4 C 1.28080(19) 0.54475(11) 0.25914(8) 0.0415(4) Uani 1 1 d . . .
H4A H 1.3617 0.5778 0.2450 0.062 Uiso 1 1 calc R . .
H4B H 1.2980 0.5253 0.3059 0.062 Uiso 1 1 calc R . .
H4C H 1.1912 0.5751 0.2584 0.062 Uiso 1 1 calc R . .
H2' H 0.9320(17) 0.8017(9) 0.1718(8) 0.020(4) Uiso 1 1 d . . .
H2 H 1.1497(17) 0.5372(9) 0.1361(8) 0.017(4) Uiso 1 1 d . . .
H1N H 0.9914(19) 0.4407(10) 0.1475(9) 0.027(4) Uiso 1 1 d . . .
H1'N H 0.876(2) 0.6992(11) 0.2356(10) 0.033(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
S1 O1 1.4953(10) . ?
S1 N1 1.6513(11) . ?
S1 C8 1.8486(17) . ?
S1' O1' 1.4930(11) . ?
S1' N1' 1.6455(12) . ?
S1' C8' 1.8472(14) . ?
F3' C5' 1.3387(18) . ?
F1' C5' 1.3484(19) . ?
F2 C5 1.336(2) . ?
F1 C5 1.3445(18) . ?
F2' C5' 1.3457(19) . ?
F3 C5 1.3449(18) . ?
N1 C1 1.4786(17) . ?
C2 C7 1.5329(19) . ?
C2 C3 1.5332(19) . ?
C2 C1 1.5535(17) . ?
C8 C11 1.5169(19) . ?
C8 C10 1.5210(18) . ?
C8 C9 1.5298(19) . ?
N1' C1' 1.4700(17) . ?
C1 C6 1.5263(19) . ?
C1 C5 1.541(2) . ?
C10' C8' 1.521(2) . ?
C11' C8' 1.526(2) . ?
C3' C4' 1.522(2) . ?
C3' C2' 1.532(2) . ?
C5' C1' 1.534(2) . ?
C3 C4 1.528(2) . ?
C8' C9' 1.525(2) . ?
C6' C1' 1.5314(18) . ?
C7' C2' 1.5332(19) . ?
C1' C2' 1.558(2) . ?

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 N1 110.77(5) . . ?
O1 S1 C8 104.85(6) . . ?
N1 S1 C8 100.34(6) . . ?
O1' S1' N1' 110.77(6) . . ?
O1' S1' C8' 104.43(6) . . ?
N1' S1' C8' 99.99(6) . . ?
C1 N1 S1 120.45(9) . . ?
C7 C2 C3 110.42(11) . . ?
C7 C2 C1 114.28(11) . . ?
C3 C2 C1 110.74(11) . . ?
C11 C8 C10 112.75(12) . . ?
C11 C8 C9 110.60(12) . . ?
C10 C8 C9 110.79(12) . . ?
C11 C8 S1 111.25(9) . . ?
C10 C8 S1 107.60(9) . . ?
C9 C8 S1 103.42(10) . . ?
C1' N1' S1' 122.00(9) . . ?
N1 C1 C6 113.02(11) . . ?
N1 C1 C5 104.57(11) . . ?
C6 C1 C5 107.98(12) . . ?
N1 C1 C2 108.04(10) . . ?
C6 C1 C2 112.24(11) . . ?
C5 C1 C2 110.74(11) . . ?
C4' C3' C2' 113.03(12) . . ?
F3' C5' F2' 107.03(13) . . ?
F3' C5' F1' 106.32(13) . . ?
F2' C5' F1' 105.82(12) . . ?
F3' C5' C1' 112.52(12) . . ?
F2' C5' C1' 113.13(13) . . ?
F1' C5' C1' 111.53(13) . . ?
C4 C3 C2 112.49(13) . . ?
C10' C8' C9' 110.84(13) . . ?
C10' C8' C11' 112.28(12) . . ?
C9' C8' C11' 110.89(13) . . ?
C10' C8' S1' 110.10(10) . . ?
C9' C8' S1' 103.88(10) . . ?
C11' C8' S1' 108.50(10) . . ?
F2 C5 F1 106.93(13) . . ?
F2 C5 F3 107.17(13) . . ?
F1 C5 F3 105.52(12) . . ?
F2 C5 C1 112.58(12) . . ?
F1 C5 C1 111.06(12) . . ?
F3 C5 C1 113.13(12) . . ?
N1' C1' C6' 112.59(11) . . ?
N1' C1' C5' 105.28(11) . . ?
C6' C1' C5' 107.76(12) . . ?
N1' C1' C2' 106.98(11) . . ?
C6' C1' C2' 112.65(12) . . ?
C5' C1' C2' 111.39(12) . . ?
C3' C2' C7' 110.31(13) . . ?
C3' C2' C1' 110.10(11) . . ?
C7' C2' C1' 114.85(12) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        72.44
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_cu_14fg009_0m
_database_code_depnum_ccdc_archive 'CCDC 1577909'
_audit_update_record             
;
2017-10-03 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H40 F6 N2 O4 S2'
_chemical_formula_weight         574.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   11.039(5)
_cell_length_b                   12.316(5)
_cell_length_c                   21.359(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2903.9(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      4.14
_cell_measurement_theta_max      65.16

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    2.272
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26534
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         65.16
_reflns_number_total             4953
_reflns_number_gt                4509
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0680P)²+1.0886P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.077(19)
_refine_ls_number_reflns         4953
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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 -0.08507(6) -0.07846(6) 0.04738(4) 0.02256(18) Uani 1 1 d . . .
S1' S 0.24408(7) 0.20066(7) 0.18976(4) 0.02805(19) Uani 1 1 d . . .
F2 F -0.09904(18) 0.20114(16) 0.09489(9) 0.0363(5) Uani 1 1 d . . .
F3 F -0.28034(19) 0.26515(15) 0.09135(10) 0.0404(5) Uani 1 1 d . . .
O2 O -0.3259(2) 0.0726(2) -0.07809(11) 0.0314(5) Uani 1 1 d . . .
F1 F -0.17924(19) 0.24036(15) 0.00625(10) 0.0362(5) Uani 1 1 d . . .
F1' F 0.29217(18) -0.03453(17) 0.32240(10) 0.0407(5) Uani 1 1 d . . .
O1 O -0.1427(2) -0.18552(18) 0.03299(11) 0.0323(5) Uani 1 1 d . . .
F3' F 0.1536(2) -0.14392(15) 0.28956(11) 0.0436(5) Uani 1 1 d . . .
O1' O 0.1661(2) 0.2987(2) 0.18226(12) 0.0398(6) Uani 1 1 d . . .
F2' F 0.2876(2) -0.07982(18) 0.22631(11) 0.0505(6) Uani 1 1 d . . .
N1 N -0.1683(2) 0.0208(2) 0.01970(14) 0.0241(6) Uani 1 1 d . . .
O2' O 0.1795(3) 0.1688(3) 0.37759(13) 0.0457(7) Uani 1 1 d . . .
N1' N 0.2124(2) 0.1375(2) 0.25456(13) 0.0253(6) Uani 1 1 d . . .
C7 C -0.2031(3) 0.1975(3) 0.06332(15) 0.0297(7) Uani 1 1 d . . .
C1 C -0.2533(3) 0.0820(3) 0.05927(14) 0.0230(6) Uani 1 1 d . . .
C5 C -0.3975(3) 0.1296(3) -0.03361(16) 0.0305(8) Uani 1 1 d . . .
H5A H -0.4819 0.1269 -0.0461 0.037 Uiso 1 1 calc R . .
H5B H -0.3728 0.2052 -0.0325 0.037 Uiso 1 1 calc R . .
C3 C -0.4354(3) -0.0332(3) 0.03273(16) 0.0287(7) Uani 1 1 d . . .
C2 C -0.3837(3) 0.0802(3) 0.03122(16) 0.0269(7) Uani 1 1 d . . .
C1' C 0.1331(3) 0.0425(3) 0.26012(15) 0.0266(7) Uani 1 1 d . . .
C6 C -0.2582(3) 0.0379(3) 0.12634(14) 0.0297(7) Uani 1 1 d . . .
H6A H -0.2858 -0.0360 0.1257 0.045 Uiso 1 1 calc R . .
H6B H -0.3131 0.0811 0.1507 0.045 Uiso 1 1 calc R . .
H6C H -0.1788 0.0410 0.1446 0.045 Uiso 1 1 calc R . .
C9' C 0.3816(3) 0.3286(3) 0.26915(18) 0.0403(9) Uani 1 1 d . . .
H9D H 0.3578 0.2866 0.3049 0.061 Uiso 1 1 calc R . .
H9E H 0.3211 0.3827 0.2607 0.061 Uiso 1 1 calc R . .
H9F H 0.4577 0.3636 0.2775 0.061 Uiso 1 1 calc R . .
C9 C 0.0048(4) -0.0964(3) -0.07280(16) 0.0366(8) Uani 1 1 d . . .
H9A H 0.0748 -0.1021 -0.0993 0.055 Uiso 1 1 calc R . .
H9B H -0.0469 -0.0394 -0.0879 0.055 Uiso 1 1 calc R . .
H9C H -0.0387 -0.1639 -0.0732 0.055 Uiso 1 1 calc R . .
C5' C 0.0947(4) 0.0811(3) 0.37832(16) 0.0369(8) Uani 1 1 d . . .
H5'A H 0.0301 0.0977 0.4076 0.044 Uiso 1 1 calc R . .
H5'B H 0.1351 0.0158 0.3929 0.044 Uiso 1 1 calc R . .
C8 C 0.0443(3) -0.0709(3) -0.00658(16) 0.0292(7) Uani 1 1 d . . .
C7' C 0.2170(3) -0.0541(3) 0.27474(17) 0.0328(8) Uani 1 1 d . . .
C3' C -0.0475(3) 0.1474(3) 0.2966(2) 0.0429(10) Uani 1 1 d . . .
C6' C 0.0682(4) 0.0163(3) 0.19882(17) 0.0416(9) Uani 1 1 d . . .
H6'A H 0.0209 0.0779 0.1860 0.062 Uiso 1 1 calc R . .
H6'B H 0.0159 -0.0451 0.2049 0.062 Uiso 1 1 calc R . .
H6'C H 0.1269 -0.0003 0.1671 0.062 Uiso 1 1 calc R . .
C2' C 0.0404(3) 0.0598(3) 0.31384(17) 0.0286(7) Uani 1 1 d . . .
C10 C 0.1294(3) -0.1582(3) 0.0185(2) 0.0416(9) Uani 1 1 d . . .
H10A H 0.0912 -0.2279 0.0151 0.062 Uiso 1 1 calc R . .
H10B H 0.1477 -0.1435 0.0616 0.062 Uiso 1 1 calc R . .
H10C H 0.2031 -0.1581 -0.0054 0.062 Uiso 1 1 calc R . .
C11 C 0.1018(3) 0.0406(3) -0.0005(2) 0.0395(9) Uani 1 1 d . . .
H11A H 0.1790 0.0408 -0.0212 0.059 Uiso 1 1 calc R . .
H11B H 0.1128 0.0576 0.0430 0.059 Uiso 1 1 calc R . .
H11C H 0.0500 0.0939 -0.0194 0.059 Uiso 1 1 calc R . .
C8' C 0.3947(3) 0.2545(3) 0.21277(16) 0.0312(8) Uani 1 1 d . . .
C10' C 0.4361(3) 0.3169(3) 0.15538(19) 0.0440(10) Uani 1 1 d . . .
H10D H 0.5188 0.3391 0.1608 0.066 Uiso 1 1 calc R . .
H10E H 0.3859 0.3798 0.1499 0.066 Uiso 1 1 calc R . .
H10F H 0.4299 0.2711 0.1191 0.066 Uiso 1 1 calc R . .
C11' C 0.4759(3) 0.1581(3) 0.22597(19) 0.0412(9) Uani 1 1 d . . .
H11D H 0.5581 0.1825 0.2305 0.062 Uiso 1 1 calc R . .
H11E H 0.4709 0.1075 0.1919 0.062 Uiso 1 1 calc R . .
H11F H 0.4503 0.1233 0.2639 0.062 Uiso 1 1 calc R . .
C4 C -0.5413(3) -0.0586(3) 0.0553(2) 0.0424(9) Uani 1 1 d . . .
C4' C -0.1647(4) 0.1399(4) 0.3037(3) 0.085(2) Uani 1 1 d . . .
H4'B H -0.1983 0.0771 0.3205 0.102 Uiso 1 1 calc R . .
H4'A H -0.2145 0.1973 0.2920 0.102 Uiso 1 1 calc R . .
H2N H 0.213(3) 0.168(3) 0.2914(18) 0.031(10) Uiso 1 1 d . . .
H1N H -0.186(4) 0.019(3) -0.015(2) 0.044(13) Uiso 1 1 d . . .
H3 H -0.387(3) -0.087(3) 0.0128(17) 0.031(9) Uiso 1 1 d . . .
H4B H -0.568(4) -0.134(3) 0.0523(19) 0.042(11) Uiso 1 1 d . . .
H3' H -0.010(4) 0.206(4) 0.285(2) 0.063(14) Uiso 1 1 d . . .
H2' H -0.008(3) -0.004(3) 0.3147(17) 0.032(10) Uiso 1 1 d . . .
H2 H -0.433(3) 0.122(3) 0.0577(17) 0.026(9) Uiso 1 1 d . . .
H4A H -0.592(4) -0.006(3) 0.0770(18) 0.036(10) Uiso 1 1 d . . .
H2O H 0.162(4) 0.212(4) 0.397(2) 0.040(14) Uiso 1 1 d . . .
H1O H -0.321(5) 0.111(4) -0.106(3) 0.072(18) 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
S1 O1 1.496(2) . ?
S1 N1 1.640(3) . ?
S1 C8 1.838(3) . ?
S1' O1' 1.491(3) . ?
S1' N1' 1.626(3) . ?
S1' C8' 1.856(3) . ?
F2 C7 1.333(4) . ?
F3 C7 1.334(4) . ?
O2 C5 1.422(4) . ?
F1 C7 1.354(4) . ?
F1' C7' 1.335(4) . ?
F3' C7' 1.347(4) . ?
F2' C7' 1.333(4) . ?
N1 C1 1.471(4) . ?
O2' C5' 1.430(5) . ?
N1' C1' 1.466(4) . ?
C7 C1 1.529(5) . ?
C1 C6 1.533(4) . ?
C1 C2 1.559(4) . ?
C5 C2 1.520(5) . ?
C3 C4 1.303(5) . ?
C3 C2 1.509(5) . ?
C1' C6' 1.527(5) . ?
C1' C7' 1.540(5) . ?
C1' C2' 1.553(5) . ?
C9' C8' 1.518(5) . ?
C9 C8 1.513(5) . ?
C5' C2' 1.525(5) . ?
C8 C11 1.518(5) . ?
C8 C10 1.525(5) . ?
C3' C4' 1.306(6) . ?
C3' C2' 1.497(5) . ?
C8' C11' 1.514(5) . ?
C8' C10' 1.517(5) . ?

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 N1 110.17(14) . . ?
O1 S1 C8 104.27(15) . . ?
N1 S1 C8 99.87(15) . . ?
O1' S1' N1' 110.77(14) . . ?
O1' S1' C8' 104.85(15) . . ?
N1' S1' C8' 97.94(15) . . ?
C1 N1 S1 122.2(2) . . ?
C1' N1' S1' 125.4(2) . . ?
F2 C7 F3 107.6(3) . . ?
F2 C7 F1 105.9(3) . . ?
F3 C7 F1 106.5(3) . . ?
F2 C7 C1 111.9(3) . . ?
F3 C7 C1 112.0(3) . . ?
F1 C7 C1 112.5(3) . . ?
N1 C1 C7 106.1(2) . . ?
N1 C1 C6 112.2(3) . . ?
C7 C1 C6 106.8(3) . . ?
N1 C1 C2 111.2(3) . . ?
C7 C1 C2 111.7(3) . . ?
C6 C1 C2 108.8(3) . . ?
O2 C5 C2 110.8(3) . . ?
C4 C3 C2 124.7(4) . . ?
C3 C2 C5 110.6(3) . . ?
C3 C2 C1 110.7(3) . . ?
C5 C2 C1 115.9(3) . . ?
N1' C1' C6' 112.3(3) . . ?
N1' C1' C7' 105.9(2) . . ?
C6' C1' C7' 107.0(3) . . ?
N1' C1' C2' 110.1(3) . . ?
C6' C1' C2' 110.7(3) . . ?
C7' C1' C2' 110.7(3) . . ?
O2' C5' C2' 112.2(3) . . ?
C9 C8 C11 112.9(3) . . ?
C9 C8 C10 111.1(3) . . ?
C11 C8 C10 110.5(3) . . ?
C9 C8 S1 110.6(2) . . ?
C11 C8 S1 108.5(2) . . ?
C10 C8 S1 102.9(2) . . ?
F2' C7' F1' 105.8(3) . . ?
F2' C7' F3' 107.0(3) . . ?
F1' C7' F3' 107.0(3) . . ?
F2' C7' C1' 112.2(3) . . ?
F1' C7' C1' 112.9(3) . . ?
F3' C7' C1' 111.7(3) . . ?
C4' C3' C2' 124.2(4) . . ?
C3' C2' C5' 110.7(3) . . ?
C3' C2' C1' 110.1(3) . . ?
C5' C2' C1' 115.6(3) . . ?
C11' C8' C10' 111.7(3) . . ?
C11' C8' C9' 112.3(3) . . ?
C10' C8' C9' 111.4(3) . . ?
C11' C8' S1' 107.4(2) . . ?
C10' C8' S1' 103.7(2) . . ?
C9' C8' S1' 109.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        65.16
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_cu_15fg010_0m
_database_code_depnum_ccdc_archive 'CCDC 1577910'
_audit_update_record             
;
2017-10-03 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H24 F3 N O2 S'
_chemical_formula_weight         351.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.212(5)
_cell_length_b                   9.456(5)
_cell_length_c                   10.583(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 112.258(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     853.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      4.51
_cell_measurement_theta_max      74.50

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    2.039
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31009
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.51
_diffrn_reflns_theta_max         74.51
_reflns_number_total             3464
_reflns_number_gt                3424
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0405P)²+0.1597P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.046(9)
_refine_ls_number_reflns         3464
_refine_ls_number_parameters     224
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0553
_refine_ls_wR_factor_gt          0.0552
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_chemical_absolute_configuration ad

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 0.25904(3) 0.63186(3) 0.32660(2) 0.01653(7) Uani 1 1 d . . .
F1 F -0.00849(8) 0.75995(9) 0.56445(8) 0.02794(17) Uani 1 1 d . . .
F2 F 0.17216(9) 0.73353(9) 0.76419(7) 0.02656(17) Uani 1 1 d . . .
F3 F 0.07044(9) 0.55146(8) 0.63928(8) 0.02459(17) Uani 1 1 d . . .
O2 O 0.33230(10) 0.49188(10) 0.31979(9) 0.02238(19) Uani 1 1 d . . .
O1 O 0.72852(11) 0.74453(11) 0.83793(9) 0.02511(19) Uani 1 1 d . . .
N1 N 0.17736(10) 0.62007(12) 0.44335(10) 0.01709(18) Uani 1 1 d . . .
C1 C 0.40553(12) 0.63152(14) 0.67952(10) 0.01509(19) Uani 1 1 d . . .
C8 C 0.53997(12) 0.64229(14) 0.62671(11) 0.0172(2) Uani 1 1 d . . .
H8A H 0.5293 0.5670 0.5616 0.021 Uiso 1 1 calc R . .
H8B H 0.5322 0.7317 0.5797 0.021 Uiso 1 1 calc R . .
C9 C 0.70048(13) 0.63185(16) 0.74248(11) 0.0215(2) Uani 1 1 d . . .
H9A H 0.7078 0.5426 0.7897 0.026 Uiso 1 1 calc R . .
H9B H 0.7811 0.6327 0.7044 0.026 Uiso 1 1 calc R . .
C2 C 0.39536(13) 0.48150(13) 0.72694(12) 0.0168(2) Uani 1 1 d . . .
C4 C 0.37411(15) 0.22868(14) 0.68784(14) 0.0233(2) Uani 1 1 d . . .
H4 H 0.3614 0.1523 0.6292 0.028 Uiso 1 1 calc R . .
C13 C 0.08101(13) 0.64366(14) 0.17015(11) 0.0186(2) Uani 1 1 d . . .
C10 C 0.24781(13) 0.69423(12) 0.57511(12) 0.0161(2) Uani 1 1 d . . .
C3 C 0.37750(14) 0.36519(13) 0.64083(13) 0.0197(2) Uani 1 1 d . . .
H3 H 0.3678 0.3794 0.5510 0.024 Uiso 1 1 calc R . .
C14 C -0.02876(15) 0.52025(13) 0.15888(13) 0.0227(3) Uani 1 1 d . . .
H14A H -0.0660 0.5248 0.2321 0.034 Uiso 1 1 calc R . .
H14B H 0.0266 0.4330 0.1643 0.034 Uiso 1 1 calc R . .
H14C H -0.1162 0.5250 0.0731 0.034 Uiso 1 1 calc R . .
C6 C 0.40708(15) 0.31965(16) 0.90817(14) 0.0272(3) Uani 1 1 d . . .
H6 H 0.4168 0.3046 0.9979 0.033 Uiso 1 1 calc R . .
C7 C 0.41005(14) 0.45674(14) 0.86126(12) 0.0221(3) Uani 1 1 d . . .
H7 H 0.4220 0.5327 0.9201 0.027 Uiso 1 1 calc R . .
C15 C 0.00484(15) 0.78572(14) 0.17636(14) 0.0233(3) Uani 1 1 d . . .
H15A H -0.0815 0.8022 0.0915 0.035 Uiso 1 1 calc R . .
H15B H 0.0807 0.8599 0.1919 0.035 Uiso 1 1 calc R . .
H15C H -0.0326 0.7843 0.2496 0.035 Uiso 1 1 calc R . .
C12 C 0.26834(15) 0.85171(13) 0.55174(13) 0.0221(2) Uani 1 1 d . . .
H12A H 0.3413 0.8624 0.5074 0.033 Uiso 1 1 calc R . .
H12B H 0.3075 0.9000 0.6380 0.033 Uiso 1 1 calc R . .
H12C H 0.1690 0.8914 0.4952 0.033 Uiso 1 1 calc R . .
C5 C 0.38958(15) 0.20564(14) 0.82132(15) 0.0262(3) Uani 1 1 d . . .
H5 H 0.3883 0.1140 0.8527 0.031 Uiso 1 1 calc R . .
C16 C 0.14243(15) 0.64219(18) 0.05402(12) 0.0260(3) Uani 1 1 d . . .
H16A H 0.1910 0.5526 0.0528 0.039 Uiso 1 1 calc R . .
H16B H 0.2180 0.7165 0.0682 0.039 Uiso 1 1 calc R . .
H16C H 0.0567 0.6566 -0.0316 0.039 Uiso 1 1 calc R . .
C11 C 0.12020(15) 0.68465(13) 0.63629(13) 0.0204(2) Uani 1 1 d . . .
H1N H 0.144(2) 0.535(2) 0.4479(18) 0.029(4) Uiso 1 1 d . . .
H1 H 0.4298(17) 0.6909(15) 0.7544(16) 0.014(3) Uiso 1 1 d . . .
H1O H 0.713(2) 0.811(2) 0.796(2) 0.038(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
S1 O2 1.4999(11) . ?
S1 N1 1.6762(11) . ?
S1 C13 1.8402(13) . ?
F1 C11 1.3445(15) . ?
F2 C11 1.3357(16) . ?
F3 C11 1.3448(16) . ?
O1 C9 1.4229(17) . ?
N1 C10 1.4737(16) . ?
C1 C2 1.5194(18) . ?
C1 C8 1.5430(15) . ?
C1 C10 1.5708(16) . ?
C8 C9 1.5247(16) . ?
C2 C7 1.3957(18) . ?
C2 C3 1.3977(18) . ?
C4 C5 1.382(2) . ?
C4 C3 1.3880(19) . ?
C13 C14 1.5189(18) . ?
C13 C15 1.5285(19) . ?
C13 C16 1.5355(16) . ?
C10 C12 1.5329(18) . ?
C10 C11 1.5447(17) . ?
C6 C5 1.386(2) . ?
C6 C7 1.392(2) . ?

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 N1 108.21(6) . . ?
O2 S1 C13 105.91(6) . . ?
N1 S1 C13 99.86(6) . . ?
C10 N1 S1 120.40(8) . . ?
C2 C1 C8 109.86(10) . . ?
C2 C1 C10 115.37(9) . . ?
C8 C1 C10 112.07(9) . . ?
C9 C8 C1 111.83(10) . . ?
O1 C9 C8 112.46(11) . . ?
C7 C2 C3 118.30(12) . . ?
C7 C2 C1 119.92(11) . . ?
C3 C2 C1 121.74(11) . . ?
C5 C4 C3 120.35(12) . . ?
C14 C13 C15 112.07(11) . . ?
C14 C13 C16 111.49(11) . . ?
C15 C13 C16 110.90(11) . . ?
C14 C13 S1 111.35(9) . . ?
C15 C13 S1 106.37(9) . . ?
C16 C13 S1 104.27(9) . . ?
N1 C10 C12 110.28(10) . . ?
N1 C10 C11 103.67(10) . . ?
C12 C10 C11 106.53(9) . . ?
N1 C10 C1 116.39(10) . . ?
C12 C10 C1 110.03(10) . . ?
C11 C10 C1 109.33(10) . . ?
C4 C3 C2 120.74(12) . . ?
C5 C6 C7 120.06(13) . . ?
C6 C7 C2 120.80(12) . . ?
C4 C5 C6 119.75(12) . . ?
F2 C11 F3 107.14(10) . . ?
F2 C11 F1 106.89(10) . . ?
F3 C11 F1 105.89(10) . . ?
F2 C11 C10 111.53(11) . . ?
F3 C11 C10 112.65(9) . . ?
F1 C11 C10 112.33(11) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        74.51
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.035
