# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_gbh34ltc_2o
_database_code_depnum_ccdc_archive 'CCDC 1490050'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 F N O2 S'
_chemical_formula_sum            'C14 H20 F N O2 S'
_chemical_formula_weight         285.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.93270(19)
_cell_length_b                   9.5312(2)
_cell_length_c                   19.6547(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.885(2)
_cell_angle_gamma                90.00
_cell_volume                     1459.33(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    99.9(1)
_cell_measurement_reflns_used    8916
_cell_measurement_theta_min      4.2140
_cell_measurement_theta_max      29.6250

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 SCALE3 ABSPACK
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2836
_diffrn_reflns_number            17380
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0222
_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       26
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         28.05
_reflns_number_total             3544
_reflns_number_gt                3147
_reflns_threshold_expression     I>2σ(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macraeet al., 2006)'

_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.
;
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.6645   57.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   28.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.6645   57.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00   64.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.6645   77.0000 -120.0000 108

#__ type_ start__ end____ width___ exp.time_
  4 omega  -87.00   17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.6645  -57.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
  5 omega  -91.00  -47.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.6645  -77.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega  -61.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       12.9770  -57.0000  150.0000 104 
;


_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)+(0.0416P)²+0.7758P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3544
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.68361(4) 0.82490(3) 0.536113(17) 0.02017(10) Uani 1 1 d . . .
F1 F 0.99496(12) 1.00465(10) 0.75176(5) 0.0334(2) Uani 1 1 d . . .
O1 O 0.84686(13) 0.75621(11) 0.54788(6) 0.0273(2) Uani 1 1 d . . .
O2 O 0.61505(13) 0.88040(11) 0.46838(5) 0.0246(2) Uani 1 1 d . . .
N1 N 0.69651(16) 0.95732(12) 0.58834(6) 0.0212(2) Uani 1 1 d . . .
C1 C 0.53283(17) 0.70583(14) 0.55781(7) 0.0197(3) Uani 1 1 d . . .
H1N H 0.612(2) 1.008(2) 0.5785(9) 0.030(5) Uiso 1 1 d . . .
C2 C 0.36067(18) 0.74608(16) 0.54670(8) 0.0248(3) Uani 1 1 d . . .
H2 H 0.325(2) 0.839(2) 0.5282(9) 0.031(5) Uiso 1 1 d . . .
C3 C 0.24044(19) 0.65173(17) 0.56153(8) 0.0273(3) Uani 1 1 d . . .
H3 H 0.123(2) 0.677(2) 0.5546(9) 0.032(5) Uiso 1 1 d . . .
C4 C 0.2877(2) 0.51783(16) 0.58651(7) 0.0258(3) Uani 1 1 d . . .
C5 C 0.4601(2) 0.48109(16) 0.59798(8) 0.0279(3) Uani 1 1 d . . .
H5 H 0.494(2) 0.389(2) 0.6149(10) 0.036(5) Uiso 1 1 d . . .
C6 C 0.58362(19) 0.57450(15) 0.58386(7) 0.0248(3) Uani 1 1 d . . .
H6 H 0.701(2) 0.5465(19) 0.5913(9) 0.030(5) Uiso 1 1 d . . .
C7 C 0.1524(2) 0.4162(2) 0.60018(9) 0.0357(4) Uani 1 1 d . . .
H7A H 0.096(3) 0.454(2) 0.6351(12) 0.049(6) Uiso 1 1 d . . .
H7B H 0.203(3) 0.327(3) 0.6193(13) 0.068(7) Uiso 1 1 d . . .
H7C H 0.072(3) 0.399(2) 0.5579(12) 0.056(6) Uiso 1 1 d . . .
C8 C 0.77032(18) 0.93832(15) 0.66269(7) 0.0233(3) Uani 1 1 d . . .
H8 H 0.818(2) 0.8424(19) 0.6681(8) 0.023(4) Uiso 1 1 d . . .
C9 C 0.6340(2) 0.95655(17) 0.70796(8) 0.0287(3) Uani 1 1 d . . .
H9A H 0.537(2) 0.893(2) 0.6897(9) 0.033(5) Uiso 1 1 d . . .
H9B H 0.687(2) 0.921(2) 0.7551(10) 0.037(5) Uiso 1 1 d . . .
C10 C 0.5738(2) 1.10793(18) 0.71031(8) 0.0311(3) Uani 1 1 d . . .
H10A H 0.513(2) 1.136(2) 0.6650(10) 0.035(5) Uiso 1 1 d . . .
H10B H 0.493(3) 1.115(2) 0.7427(10) 0.039(5) Uiso 1 1 d . . .
C11 C 0.7240(2) 1.20784(18) 0.73176(8) 0.0304(3) Uani 1 1 d . . .
H11A H 0.780(2) 1.188(2) 0.7801(11) 0.038(5) Uiso 1 1 d . . .
H11B H 0.685(2) 1.306(2) 0.7307(9) 0.031(5) Uiso 1 1 d . . .
C12 C 0.8559(2) 1.19183(16) 0.68489(8) 0.0280(3) Uani 1 1 d . . .
H12A H 0.957(3) 1.256(2) 0.6983(10) 0.039(5) Uiso 1 1 d . . .
H12B H 0.8043(18) 1.2264(15) 0.6378(8) 0.010(3) Uiso 1 1 d . . .
C13 C 0.91943(19) 1.04218(15) 0.68252(7) 0.0246(3) Uani 1 1 d . . .
C14 C 1.0586(2) 1.02503(19) 0.64017(9) 0.0322(3) Uani 1 1 d . . .
H14A H 1.013(2) 1.057(2) 0.5939(10) 0.032(5) Uiso 1 1 d . . .
H14B H 1.091(2) 0.923(2) 0.6395(10) 0.038(5) Uiso 1 1 d . . .
H14C H 1.158(2) 1.084(2) 0.6591(10) 0.037(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 1.4304(10) . ?
S1 O2 1.4402(10) . ?
S1 N1 1.6179(12) . ?
S1 C1 1.7588(14) . ?
F1 C13 1.4251(16) . ?
N1 C8 1.4791(17) . ?
N1 H1N 0.821(19) . ?
C1 C6 1.3833(19) . ?
C1 C2 1.3955(19) . ?
C2 C3 1.381(2) . ?
C2 H2 0.980(19) . ?
C3 C4 1.393(2) . ?
C3 H3 0.947(19) . ?
C4 C5 1.388(2) . ?
C4 C7 1.507(2) . ?
C5 C6 1.390(2) . ?
C5 H5 0.96(2) . ?
C6 H6 0.953(18) . ?
C7 H7A 0.96(2) . ?
C7 H7B 0.99(3) . ?
C7 H7C 0.96(2) . ?
C8 C9 1.535(2) . ?
C8 C13 1.535(2) . ?
C8 H8 0.988(17) . ?
C9 C10 1.523(2) . ?
C9 H9A 0.994(19) . ?
C9 H9B 1.00(2) . ?
C10 C11 1.521(2) . ?
C10 H10A 0.967(19) . ?
C10 H10B 0.99(2) . ?
C11 C12 1.526(2) . ?
C11 H11A 0.99(2) . ?
C11 H11B 0.988(19) . ?
C12 C13 1.516(2) . ?
C12 H12A 1.00(2) . ?
C12 H12B 0.996(15) . ?
C13 C14 1.512(2) . ?
C14 H14A 0.962(19) . ?
C14 H14B 1.01(2) . ?
C14 H14C 0.98(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 O2 119.33(6) . . ?
O1 S1 N1 107.92(6) . . ?
O2 S1 N1 105.52(6) . . ?
O1 S1 C1 107.57(6) . . ?
O2 S1 C1 107.80(6) . . ?
N1 S1 C1 108.30(6) . . ?
C8 N1 S1 119.81(10) . . ?
C8 N1 H1N 117.4(13) . . ?
S1 N1 H1N 110.9(13) . . ?
C6 C1 C2 120.98(13) . . ?
C6 C1 S1 120.65(11) . . ?
C2 C1 S1 118.36(11) . . ?
C3 C2 C1 118.84(14) . . ?
C3 C2 H2 120.3(11) . . ?
C1 C2 H2 120.8(11) . . ?
C2 C3 C4 121.34(14) . . ?
C2 C3 H3 120.5(12) . . ?
C4 C3 H3 118.2(12) . . ?
C5 C4 C3 118.66(14) . . ?
C5 C4 C7 121.44(15) . . ?
C3 C4 C7 119.89(15) . . ?
C4 C5 C6 121.07(14) . . ?
C4 C5 H5 119.6(12) . . ?
C6 C5 H5 119.3(12) . . ?
C1 C6 C5 119.09(13) . . ?
C1 C6 H6 121.2(11) . . ?
C5 C6 H6 119.7(11) . . ?
C4 C7 H7A 109.5(13) . . ?
C4 C7 H7B 111.9(15) . . ?
H7A C7 H7B 105(2) . . ?
C4 C7 H7C 109.4(14) . . ?
H7A C7 H7C 111.0(19) . . ?
H7B C7 H7C 110(2) . . ?
N1 C8 C9 111.60(12) . . ?
N1 C8 C13 108.31(11) . . ?
C9 C8 C13 111.92(12) . . ?
N1 C8 H8 107.0(10) . . ?
C9 C8 H8 110.0(10) . . ?
C13 C8 H8 107.9(10) . . ?
C10 C9 C8 112.58(12) . . ?
C10 C9 H9A 111.4(11) . . ?
C8 C9 H9A 107.7(11) . . ?
C10 C9 H9B 111.9(11) . . ?
C8 C9 H9B 106.0(11) . . ?
H9A C9 H9B 106.9(15) . . ?
C11 C10 C9 111.58(14) . . ?
C11 C10 H10A 108.1(12) . . ?
C9 C10 H10A 109.7(11) . . ?
C11 C10 H10B 110.5(12) . . ?
C9 C10 H10B 109.1(12) . . ?
H10A C10 H10B 107.8(16) . . ?
C10 C11 C12 111.12(13) . . ?
C10 C11 H11A 109.4(11) . . ?
C12 C11 H11A 108.9(11) . . ?
C10 C11 H11B 111.3(11) . . ?
C12 C11 H11B 109.3(11) . . ?
H11A C11 H11B 106.7(16) . . ?
C13 C12 C11 112.48(13) . . ?
C13 C12 H12A 109.3(11) . . ?
C11 C12 H12A 112.6(11) . . ?
C13 C12 H12B 111.3(9) . . ?
C11 C12 H12B 108.7(8) . . ?
H12A C12 H12B 102.0(14) . . ?
F1 C13 C14 106.23(12) . . ?
F1 C13 C12 106.79(12) . . ?
C14 C13 C12 113.59(13) . . ?
F1 C13 C8 104.21(11) . . ?
C14 C13 C8 113.47(13) . . ?
C12 C13 C8 111.70(12) . . ?
C13 C14 H14A 107.7(11) . . ?
C13 C14 H14B 109.1(11) . . ?
H14A C14 H14B 110.3(15) . . ?
C13 C14 H14C 110.2(11) . . ?
H14A C14 H14C 107.6(16) . . ?
H14B C14 H14C 111.7(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C8 -48.59(12) . . . . ?
O2 S1 N1 C8 -177.20(10) . . . . ?
C1 S1 N1 C8 67.58(12) . . . . ?
O1 S1 C1 C6 2.42(13) . . . . ?
O2 S1 C1 C6 132.31(12) . . . . ?
N1 S1 C1 C6 -113.98(12) . . . . ?
O1 S1 C1 C2 -176.24(11) . . . . ?
O2 S1 C1 C2 -46.35(13) . . . . ?
N1 S1 C1 C2 67.36(12) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
S1 C1 C2 C3 178.00(11) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C2 C3 C4 C7 -178.24(14) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C7 C4 C5 C6 178.65(14) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
S1 C1 C6 C5 -177.58(11) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
S1 N1 C8 C9 -112.30(12) . . . . ?
S1 N1 C8 C13 124.06(11) . . . . ?
N1 C8 C9 C10 -69.88(16) . . . . ?
C13 C8 C9 C10 51.69(17) . . . . ?
C8 C9 C10 C11 -53.52(17) . . . . ?
C9 C10 C11 C12 54.81(17) . . . . ?
C10 C11 C12 C13 -55.56(18) . . . . ?
C11 C12 C13 F1 -59.49(16) . . . . ?
C11 C12 C13 C14 -176.26(13) . . . . ?
C11 C12 C13 C8 53.84(17) . . . . ?
N1 C8 C13 F1 -173.08(11) . . . . ?
C9 C8 C13 F1 63.47(15) . . . . ?
N1 C8 C13 C14 -57.98(16) . . . . ?
C9 C8 C13 C14 178.57(13) . . . . ?
N1 C8 C13 C12 71.99(15) . . . . ?
C9 C8 C13 C12 -51.46(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.048


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_gbh35lta_S2d
_database_code_depnum_ccdc_archive 'CCDC 1490051'

_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 F N O2 S'
_chemical_formula_sum            'C16 H18 F N O2 S'
_chemical_formula_weight         307.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab '


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

_cell_length_a                   8.2947(3)
_cell_length_b                   9.5293(2)
_cell_length_c                   18.8749(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1491.92(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    99.9(1)
_cell_measurement_reflns_used    8576
_cell_measurement_theta_min      3.8760
_cell_measurement_theta_max      29.7300

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.3 SCALE3 ABSPACK
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      99.9(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2836
_diffrn_reflns_number            16718
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0346
_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       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         28.06
_reflns_number_total             3614
_reflns_number_gt                3373
_reflns_threshold_expression     >2sigma(I)

_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -92.00    0.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4196  -77.0000 -120.0000 92

#__ type_ start__ end____ width___ exp.time_
  2 omega  -46.00   39.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7321  -57.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega  -92.00   20.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4196  -77.0000   90.0000 112

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00    9.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4196   57.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega  -60.00   15.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       13.7321  -57.0000  150.0000 75

;

_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macraeet al., 2006)'

_computing_publication_material  'PLATON (Spek, 2009)'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.
;

_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)+(0.0236P)²+0.7605P] 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
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 
; 
Flack H D (1983), Acta Cryst. A39, 876-881
;
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_number_reflns         3614
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0752
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42481(5) 0.59435(4) 0.24003(2) 0.01681(10) Uani 1 1 d . . .
F1 F 0.86750(14) 0.54176(11) 0.34667(6) 0.0252(3) Uani 1 1 d . . .
O1 O 0.41534(17) 0.73120(12) 0.27198(6) 0.0217(3) Uani 1 1 d . . .
O2 O 0.31176(16) 0.48893(12) 0.26184(7) 0.0225(3) Uani 1 1 d . . .
N1 N 0.60132(18) 0.53268(15) 0.25454(8) 0.0186(3) Uani 1 1 d . . .
H1N H 0.606(2) 0.448(2) 0.2495(10) 0.016(5) Uiso 1 1 d . . .
C1 C 0.4047(2) 0.61894(17) 0.14759(8) 0.0163(3) Uani 1 1 d . . .
C2 C 0.3096(2) 0.72918(18) 0.12341(10) 0.0193(4) Uani 1 1 d . . .
H2 H 0.266(2) 0.792(2) 0.1562(10) 0.015(5) Uiso 1 1 d . . .
C3 C 0.2836(3) 0.7433(2) 0.05091(10) 0.0215(4) Uani 1 1 d . . .
H3 H 0.220(3) 0.819(2) 0.0356(10) 0.016(5) Uiso 1 1 d . . .
C4 C 0.3522(2) 0.65001(19) 0.00285(10) 0.0207(4) Uani 1 1 d . . .
C5 C 0.4477(2) 0.54158(19) 0.02833(9) 0.0204(4) Uani 1 1 d . . .
H5 H 0.498(3) 0.474(2) -0.0028(12) 0.026(6) Uiso 1 1 d . . .
C6 C 0.4741(2) 0.52483(19) 0.10066(10) 0.0197(4) Uani 1 1 d . . .
H6 H 0.536(2) 0.448(2) 0.1166(10) 0.019(5) Uiso 1 1 d . . .
C7 C 0.3214(3) 0.6680(2) -0.07562(10) 0.0287(4) Uani 1 1 d . . .
H7C H 0.4030 0.6193 -0.1020 0.043 Uiso 1 1 calc R . .
H7A H 0.3241 0.7660 -0.0874 0.043 Uiso 1 1 calc R . .
H7B H 0.2174 0.6302 -0.0873 0.043 Uiso 1 1 calc R . .
C8 C 0.7444(2) 0.61839(19) 0.24113(10) 0.0193(4) Uani 1 1 d . . .
H8A H 0.713(3) 0.702(2) 0.2157(11) 0.023 Uiso 1 1 d . . .
H8B H 0.814(3) 0.566(2) 0.2124(11) 0.023 Uiso 1 1 d . . .
C9 C 0.8236(2) 0.66435(18) 0.30920(9) 0.0183(4) Uani 1 1 d . . .
H9 H 0.741(3) 0.716(2) 0.3406(11) 0.022 Uiso 1 1 d . . .
C10 C 0.9741(2) 0.7518(2) 0.29807(10) 0.0207(4) Uani 1 1 d . . .
H10A H 0.944(2) 0.826(2) 0.2682(11) 0.021(5) Uiso 1 1 d . . .
H10B H 1.051(3) 0.693(2) 0.2747(11) 0.021(5) Uiso 1 1 d . . .
C11 C 1.0404(2) 0.80677(19) 0.36753(9) 0.0190(4) Uani 1 1 d . . .
C12 C 1.1608(2) 0.73547(19) 0.40356(10) 0.0220(4) Uani 1 1 d . . .
H12 H 1.205(3) 0.654(2) 0.3846(12) 0.032(6) Uiso 1 1 d . . .
C13 C 1.2140(3) 0.7816(2) 0.46943(11) 0.0254(4) Uani 1 1 d . . .
H13 H 1.298(3) 0.729(2) 0.4911(12) 0.030(6) Uiso 1 1 d . . .
C14 C 1.1471(2) 0.9000(2) 0.49972(10) 0.0248(4) Uani 1 1 d . . .
H14 H 1.187(3) 0.932(2) 0.5461(11) 0.022(5) Uiso 1 1 d . . .
C15 C 1.0293(2) 0.9737(2) 0.46369(11) 0.0243(4) Uani 1 1 d . . .
H15 H 0.983(3) 1.051(2) 0.4841(12) 0.030(6) Uiso 1 1 d . . .
C16 C 0.9764(2) 0.9276(2) 0.39797(10) 0.0221(4) Uani 1 1 d . . .
H16 H 0.894(3) 0.976(2) 0.3753(12) 0.030(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 O2 1.4345(13) . ?
S1 O1 1.4388(12) . ?
S1 N1 1.6012(15) . ?
S1 C1 1.7683(16) . ?
F1 C9 1.413(2) . ?
N1 C8 1.463(2) . ?
N1 H1N 0.815(19) . ?
C1 C6 1.386(2) . ?
C1 C2 1.391(2) . ?
C2 C3 1.392(2) . ?
C2 H2 0.94(2) . ?
C3 C4 1.392(3) . ?
C3 H3 0.94(2) . ?
C4 C5 1.388(3) . ?
C4 C7 1.513(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.96(2) . ?
C6 H6 0.95(2) . ?
C7 H7C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C8 C9 1.508(2) . ?
C8 H8A 0.97(2) . ?
C8 H8B 0.94(2) . ?
C9 C10 1.516(3) . ?
C9 H9 1.03(2) . ?
C10 C11 1.515(2) . ?
C10 H10A 0.94(2) . ?
C10 H10B 0.95(2) . ?
C11 C12 1.386(3) . ?
C11 C16 1.392(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.93(2) . ?
C13 C14 1.381(3) . ?
C13 H13 0.95(2) . ?
C14 C15 1.383(3) . ?
C14 H14 0.98(2) . ?
C15 C16 1.387(3) . ?
C15 H15 0.92(2) . ?
C16 H16 0.93(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 O1 118.60(8) . . ?
O2 S1 N1 106.96(8) . . ?
O1 S1 N1 108.12(8) . . ?
O2 S1 C1 108.31(8) . . ?
O1 S1 C1 106.75(7) . . ?
N1 S1 C1 107.67(8) . . ?
C8 N1 S1 120.50(12) . . ?
C8 N1 H1N 119.8(14) . . ?
S1 N1 H1N 112.7(14) . . ?
C6 C1 C2 120.97(15) . . ?
C6 C1 S1 120.39(13) . . ?
C2 C1 S1 118.51(13) . . ?
C1 C2 C3 118.91(17) . . ?
C1 C2 H2 119.2(12) . . ?
C3 C2 H2 121.9(12) . . ?
C4 C3 C2 121.05(18) . . ?
C4 C3 H3 121.3(12) . . ?
C2 C3 H3 117.6(12) . . ?
C5 C4 C3 118.88(17) . . ?
C5 C4 C7 121.34(17) . . ?
C3 C4 C7 119.78(17) . . ?
C4 C5 C6 121.01(17) . . ?
C4 C5 H5 122.0(13) . . ?
C6 C5 H5 117.0(13) . . ?
C1 C6 C5 119.17(17) . . ?
C1 C6 H6 121.6(12) . . ?
C5 C6 H6 119.1(12) . . ?
C4 C7 H7C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C8 C9 111.60(15) . . ?
N1 C8 H8A 109.4(13) . . ?
C9 C8 H8A 107.3(12) . . ?
N1 C8 H8B 108.0(13) . . ?
C9 C8 H8B 112.2(13) . . ?
H8A C8 H8B 108.4(18) . . ?
F1 C9 C8 107.36(14) . . ?
F1 C9 C10 108.17(14) . . ?
C8 C9 C10 113.60(15) . . ?
F1 C9 H9 106.2(11) . . ?
C8 C9 H9 109.9(12) . . ?
C10 C9 H9 111.3(12) . . ?
C11 C10 C9 111.67(15) . . ?
C11 C10 H10A 110.8(12) . . ?
C9 C10 H10A 106.4(13) . . ?
C11 C10 H10B 111.1(12) . . ?
C9 C10 H10B 106.8(12) . . ?
H10A C10 H10B 109.9(17) . . ?
C12 C11 C16 118.54(17) . . ?
C12 C11 C10 121.11(17) . . ?
C16 C11 C10 120.29(17) . . ?
C11 C12 C13 120.82(18) . . ?
C11 C12 H12 120.1(14) . . ?
C13 C12 H12 119.0(14) . . ?
C14 C13 C12 120.06(19) . . ?
C14 C13 H13 123.0(14) . . ?
C12 C13 H13 116.9(14) . . ?
C13 C14 C15 119.70(18) . . ?
C13 C14 H14 119.3(13) . . ?
C15 C14 H14 121.0(13) . . ?
C14 C15 C16 120.17(19) . . ?
C14 C15 H15 120.0(14) . . ?
C16 C15 H15 119.8(14) . . ?
C15 C16 C11 120.68(18) . . ?
C15 C16 H16 119.1(14) . . ?
C11 C16 H16 120.1(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C8 -176.88(13) . . . . ?
O1 S1 N1 C8 -48.10(15) . . . . ?
C1 S1 N1 C8 66.90(14) . . . . ?
O2 S1 C1 C6 -78.93(16) . . . . ?
O1 S1 C1 C6 152.30(15) . . . . ?
N1 S1 C1 C6 36.41(16) . . . . ?
O2 S1 C1 C2 97.04(15) . . . . ?
O1 S1 C1 C2 -31.74(16) . . . . ?
N1 S1 C1 C2 -147.63(14) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
S1 C1 C2 C3 -175.41(15) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C3 C4 C7 179.89(18) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C7 C4 C5 C6 -179.32(18) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
S1 C1 C6 C5 175.89(14) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
S1 N1 C8 C9 108.21(15) . . . . ?
N1 C8 C9 F1 59.62(18) . . . . ?
N1 C8 C9 C10 179.17(15) . . . . ?
F1 C9 C10 C11 -66.22(19) . . . . ?
C8 C9 C10 C11 174.69(15) . . . . ?
C9 C10 C11 C12 94.7(2) . . . . ?
C9 C10 C11 C16 -82.6(2) . . . . ?
C16 C11 C12 C13 1.5(3) . . . . ?
C10 C11 C12 C13 -175.91(18) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C16 1.2(3) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C12 C11 C16 C15 -1.5(3) . . . . ?
C10 C11 C16 C15 175.90(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.06
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.053


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_gbh36_S1d
_database_code_depnum_ccdc_archive 'CCDC 1490052'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O2 S'
_chemical_formula_sum            'C16 H17 N O2 S'
_chemical_formula_weight         287.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb  '

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

_cell_length_a                   7.3082(2)
_cell_length_b                   12.6670(4)
_cell_length_c                   7.9739(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.802(3)
_cell_angle_gamma                90.00
_cell_volume                     719.82(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.5(6)
_cell_measurement_reflns_used    13646
_cell_measurement_theta_min      4.1050
_cell_measurement_theta_max      30.4610

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 SCALE3 ABSPACK.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100.5(6)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_detector_area_resol_mean 10.2836
_diffrn_reflns_number            17424
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.28
_diffrn_reflns_theta_max         28.16
_reflns_number_total             3518
_reflns_number_gt                3455
_reflns_threshold_expression     >2sigma(I)

_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -93.00   19.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7759  -77.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
  2 omega  -89.00    2.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7759  -57.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -44.00  -12.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.0884  -77.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega   -9.00   43.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.0884  -77.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega  -51.00  -12.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.0884  -57.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -44.00   27.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7759   57.0000 -120.0000 71

#__ type_ start__ end____ width___ exp.time_
  7 omega  -89.00   15.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7759  -57.0000 -180.0000 104

#__ type_ start__ end____ width___ exp.time_
  8 omega  -44.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7759   57.0000  150.0000 103

#__ type_ start__ end____ width___ exp.time_
  9 omega  -48.00   64.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.7759   77.0000  -60.0000 112

#__ type_ start__ end____ width___ exp.time_
 10 omega  -59.00   45.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.0884  -57.0000  -90.0000 104

#__ type_ start__ end____ width___ exp.time_
 11 omega  -59.00   45.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       15.0884  -57.0000   30.0000 104

;
_diffrn_measurement_method       'ω scans'

_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macraeet al., 2006)'

_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.
;

_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)+(0.0169P)²+0.2712P] 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       ?
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_number_reflns         3518
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0585
_refine_ls_wR_factor_gt          0.0581
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 1.10608(4) 0.33968(2) 0.34631(4) 0.01881(7) Uani 1 1 d . . .
O1 O 1.14245(16) 0.25351(9) 0.46614(13) 0.0291(2) Uani 1 1 d . . .
O2 O 1.26047(13) 0.40693(9) 0.33076(13) 0.0254(2) Uani 1 1 d . . .
N1 N 0.92996(16) 0.40753(9) 0.39491(14) 0.0183(2) Uani 1 1 d . . .
C1 C 0.99813(17) 0.29348(10) 0.14065(16) 0.0166(2) Uani 1 1 d . . .
C2 C 0.87641(19) 0.20793(11) 0.12424(18) 0.0210(3) Uani 1 1 d . . .
H2 H 0.849(2) 0.1738(15) 0.227(2) 0.024(4) Uiso 1 1 d . . .
C3 C 0.78736(19) 0.17461(11) -0.03857(19) 0.0222(3) Uani 1 1 d . . .
H3 H 0.706(2) 0.1181(15) -0.049(2) 0.025(5) Uiso 1 1 d . . .
C4 C 0.81665(18) 0.22574(11) -0.18527(17) 0.0198(3) Uani 1 1 d . . .
C5 C 0.94325(18) 0.30958(11) -0.16452(17) 0.0203(3) Uani 1 1 d . . .
H5 H 0.969(2) 0.3414(15) -0.262(2) 0.025(4) Uiso 1 1 d . . .
C6 C 1.03367(17) 0.34450(12) -0.00228(15) 0.0184(2) Uani 1 1 d . . .
H6 H 1.120(2) 0.4013(13) 0.0122(19) 0.017(4) Uiso 1 1 d . . .
C7 C 0.7100(2) 0.19506(12) -0.36228(19) 0.0266(3) Uani 1 1 d . . .
H7A H 0.6807 0.1211 -0.3641 0.040 Uiso 1 1 calc R . .
H7B H 0.7853 0.2094 -0.4442 0.040 Uiso 1 1 calc R . .
H7C H 0.5958 0.2351 -0.3916 0.040 Uiso 1 1 calc R . .
C8 C 0.9856(2) 0.50011(11) 0.51171(18) 0.0218(3) Uani 1 1 d . . .
H8A H 0.911(3) 0.5097(14) 0.591(2) 0.026(4) Uiso 1 1 d . . .
H8B H 1.112(2) 0.5105(13) 0.555(2) 0.024(4) Uiso 1 1 d . . .
C9 C 0.90550(19) 0.51768(10) 0.32754(17) 0.0183(2) Uani 1 1 d . . .
H9 H 0.986(2) 0.5381(12) 0.2596(19) 0.011(3) Uiso 1 1 d . . .
C10 C 0.70469(19) 0.55121(12) 0.26222(18) 0.0219(3) Uani 1 1 d . . .
H10A H 0.631(2) 0.5170(13) 0.332(2) 0.018(4) Uiso 1 1 d . . .
H10B H 0.695(2) 0.6259(14) 0.277(2) 0.023(4) Uiso 1 1 d . . .
C11 C 0.63511(17) 0.52494(11) 0.07412(17) 0.0190(3) Uani 1 1 d . . .
C12 C 0.67098(19) 0.59355(12) -0.05091(19) 0.0229(3) Uani 1 1 d . . .
H12 H 0.733(2) 0.6601(14) -0.016(2) 0.027(4) Uiso 1 1 d . . .
C13 C 0.6107(2) 0.57018(13) -0.22472(19) 0.0263(3) Uani 1 1 d . . .
H13 H 0.634(3) 0.6196(16) -0.312(3) 0.038(5) Uiso 1 1 d . . .
C14 C 0.5135(2) 0.47744(13) -0.27485(19) 0.0265(3) Uani 1 1 d . . .
H14 H 0.478(2) 0.4607(13) -0.391(2) 0.023(4) Uiso 1 1 d . . .
C15 C 0.47746(19) 0.40865(12) -0.1510(2) 0.0256(3) Uani 1 1 d . . .
H15 H 0.409(3) 0.3439(18) -0.184(2) 0.040(5) Uiso 1 1 d . . .
C16 C 0.53848(18) 0.43154(11) 0.02261(19) 0.0221(3) Uani 1 1 d . . .
H16 H 0.515(2) 0.3838(14) 0.111(2) 0.028(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 1.4361(11) . ?
S1 O2 1.4409(11) . ?
S1 N1 1.6633(11) . ?
S1 C1 1.7552(13) . ?
N1 C9 1.4917(17) . ?
N1 C8 1.4968(18) . ?
C1 C6 1.3840(18) . ?
C1 C2 1.3897(18) . ?
C2 C3 1.383(2) . ?
C2 H2 0.989(18) . ?
C3 C4 1.395(2) . ?
C3 H3 0.924(19) . ?
C4 C5 1.3940(18) . ?
C4 C7 1.5044(19) . ?
C5 C6 1.3882(17) . ?
C5 H5 0.930(17) . ?
C6 H6 0.946(16) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.4724(19) . ?
C8 H8A 0.930(18) . ?
C8 H8B 0.921(17) . ?
C9 C10 1.5056(18) . ?
C9 H9 0.923(15) . ?
C10 C11 1.5103(18) . ?
C10 H10A 0.963(17) . ?
C10 H10B 0.958(18) . ?
C11 C12 1.391(2) . ?
C11 C16 1.3924(19) . ?
C12 C13 1.390(2) . ?
C12 H12 0.968(18) . ?
C13 C14 1.385(2) . ?
C13 H13 0.98(2) . ?
C14 C15 1.386(2) . ?
C14 H14 0.926(17) . ?
C15 C16 1.387(2) . ?
C15 H15 0.97(2) . ?
C16 H16 0.970(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.27(7) . . ?
O1 S1 N1 106.04(6) . . ?
O2 S1 N1 112.07(6) . . ?
O1 S1 C1 110.29(7) . . ?
O2 S1 C1 108.37(6) . . ?
N1 S1 C1 100.32(6) . . ?
C9 N1 C8 59.03(8) . . ?
C9 N1 S1 115.89(9) . . ?
C8 N1 S1 115.62(9) . . ?
C6 C1 C2 121.31(12) . . ?
C6 C1 S1 119.09(10) . . ?
C2 C1 S1 119.59(10) . . ?
C3 C2 C1 118.99(12) . . ?
C3 C2 H2 120.5(10) . . ?
C1 C2 H2 120.4(10) . . ?
C2 C3 C4 121.19(13) . . ?
C2 C3 H3 118.9(11) . . ?
C4 C3 H3 119.9(11) . . ?
C5 C4 C3 118.39(12) . . ?
C5 C4 C7 120.03(13) . . ?
C3 C4 C7 121.54(13) . . ?
C6 C5 C4 121.31(13) . . ?
C6 C5 H5 119.7(11) . . ?
C4 C5 H5 119.0(11) . . ?
C1 C6 C5 118.77(13) . . ?
C1 C6 H6 119.7(9) . . ?
C5 C6 H6 121.5(9) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N1 60.31(8) . . ?
C9 C8 H8A 119.8(11) . . ?
N1 C8 H8A 114.0(11) . . ?
C9 C8 H8B 119.5(11) . . ?
N1 C8 H8B 117.0(11) . . ?
H8A C8 H8B 114.7(15) . . ?
C8 C9 N1 60.66(9) . . ?
C8 C9 C10 121.96(12) . . ?
N1 C9 C10 114.73(11) . . ?
C8 C9 H9 117.6(9) . . ?
N1 C9 H9 115.6(10) . . ?
C10 C9 H9 114.8(9) . . ?
C9 C10 C11 111.67(11) . . ?
C9 C10 H10A 107.6(9) . . ?
C11 C10 H10A 111.6(9) . . ?
C9 C10 H10B 109.1(10) . . ?
C11 C10 H10B 108.6(10) . . ?
H10A C10 H10B 108.1(14) . . ?
C12 C11 C16 118.90(13) . . ?
C12 C11 C10 119.93(13) . . ?
C16 C11 C10 121.15(12) . . ?
C13 C12 C11 120.89(13) . . ?
C13 C12 H12 119.8(10) . . ?
C11 C12 H12 119.2(10) . . ?
C14 C13 C12 119.83(14) . . ?
C14 C13 H13 119.7(12) . . ?
C12 C13 H13 120.5(12) . . ?
C13 C14 C15 119.60(14) . . ?
C13 C14 H14 119.7(11) . . ?
C15 C14 H14 120.7(11) . . ?
C14 C15 C16 120.65(14) . . ?
C14 C15 H15 120.6(11) . . ?
C16 C15 H15 118.8(11) . . ?
C15 C16 C11 120.12(13) . . ?
C15 C16 H16 121.5(10) . . ?
C11 C16 H16 118.4(10) . . ?

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 C9 161.44(9) . . . . ?
O2 S1 N1 C9 31.03(11) . . . . ?
C1 S1 N1 C9 -83.77(10) . . . . ?
O1 S1 N1 C8 95.12(10) . . . . ?
O2 S1 N1 C8 -35.30(11) . . . . ?
C1 S1 N1 C8 -150.10(10) . . . . ?
O1 S1 C1 C6 -147.78(10) . . . . ?
O2 S1 C1 C6 -16.87(12) . . . . ?
N1 S1 C1 C6 100.70(11) . . . . ?
O1 S1 C1 C2 33.38(12) . . . . ?
O2 S1 C1 C2 164.29(10) . . . . ?
N1 S1 C1 C2 -78.14(11) . . . . ?
C6 C1 C2 C3 -1.01(19) . . . . ?
S1 C1 C2 C3 177.81(11) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 2.1(2) . . . . ?
C2 C3 C4 C7 -175.53(13) . . . . ?
C3 C4 C5 C6 -2.31(19) . . . . ?
C7 C4 C5 C6 175.37(13) . . . . ?
C2 C1 C6 C5 0.82(19) . . . . ?
S1 C1 C6 C5 -178.01(10) . . . . ?
C4 C5 C6 C1 0.88(19) . . . . ?
S1 N1 C8 C9 106.08(10) . . . . ?
N1 C8 C9 C10 102.41(14) . . . . ?
S1 N1 C9 C8 -105.62(11) . . . . ?
C8 N1 C9 C10 -114.18(13) . . . . ?
S1 N1 C9 C10 140.20(10) . . . . ?
C8 C9 C10 C11 -158.53(13) . . . . ?
N1 C9 C10 C11 -88.93(14) . . . . ?
C9 C10 C11 C12 -84.00(16) . . . . ?
C9 C10 C11 C16 94.55(15) . . . . ?
C16 C11 C12 C13 0.5(2) . . . . ?
C10 C11 C12 C13 179.04(13) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C11 0.8(2) . . . . ?
C12 C11 C16 C15 -0.82(19) . . . . ?
C10 C11 C16 C15 -179.39(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.16
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_gbh33rta_2l
_database_code_depnum_ccdc_archive 'CCDC 1490053'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2016-10-19 downloaded from the CCDC.
;
_audit_creation_method           
;
 CrysAlis PRO (Agilent, 2013) 
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H36 F2 N2 O6 S2'
_chemical_formula_sum            'C26 H36 F2 N2 O6 S2'
_chemical_formula_weight         574.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.3281(4)
_cell_length_b                   12.8693(9)
_cell_length_c                   17.8671(10)
_cell_angle_alpha                105.544(6)
_cell_angle_beta                 93.657(5)
_cell_angle_gamma                100.435(5)
_cell_volume                     1368.94(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5568
_cell_measurement_theta_min      3.5210
_cell_measurement_theta_max      25.8890

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Version 1.171.36.32 SCALE3 ABSPACK
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_detector_area_resol_mean 10.2836
_diffrn_reflns_number            18222
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         25.68
_reflns_number_total             5177
_reflns_number_gt                3840
_reflns_threshold_expression     I>2σ(I)

_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -21.00   17.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.0884  -57.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega   12.00   37.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.4009  -77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega   30.00   56.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.4009   57.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -19.00   38.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.4009  -57.0000  -90.0000 57

#__ type_ start__ end____ width___ exp.time_
  5 omega  -60.00   26.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.4009  -57.0000   60.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega   -7.00   88.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.4009   77.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
  7 omega  -83.00   14.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       -9.0884  -57.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
  8 omega  -65.00   39.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -        9.4009  -57.0000 -150.0000 104

;

_computing_cell_refinement       'CrysAlis PRO (Agilent, 2013)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 1997) and Mercury (Macraeet al., 2006)'

_computing_publication_material  'PLATON (Spek, 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.
;

_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)+(0.0146P)²+0.7143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5177
_refine_ls_number_parameters     476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61638(8) 0.49996(4) 0.25542(3) 0.04061(14) Uani 1 1 d . . .
O1 O 0.7080(3) 0.52093(13) 0.33449(9) 0.0567(4) Uani 1 1 d . . .
O2 O 0.3897(2) 0.49761(12) 0.24039(10) 0.0553(4) Uani 1 1 d . . .
O3 O 0.6900(2) 0.79546(12) 0.20580(9) 0.0451(4) Uani 1 1 d . . .
H30 H 0.619(4) 0.841(2) 0.2193(14) 0.058(8) Uiso 1 1 d . . .
F1 F 0.9965(2) 0.54588(11) 0.09654(8) 0.0661(4) Uani 1 1 d . . .
N1 N 0.7477(3) 0.59321(14) 0.22260(10) 0.0395(4) Uani 1 1 d . . .
H1N H 0.873(3) 0.6169(17) 0.2436(12) 0.043(6) Uiso 1 1 d . . .
C1 C 0.6862(3) 0.60750(16) 0.14608(12) 0.0373(5) Uani 1 1 d . . .
H1 H 0.598(3) 0.5420(16) 0.1150(11) 0.039(5) Uiso 1 1 d . . .
C2 C 0.5566(3) 0.69838(16) 0.15330(12) 0.0389(5) Uani 1 1 d . . .
H2 H 0.425(3) 0.6777(15) 0.1772(11) 0.036(5) Uiso 1 1 d . . .
C3 C 0.5008(4) 0.7157(2) 0.07452(15) 0.0522(6) Uani 1 1 d . . .
H3A H 0.422(3) 0.7726(18) 0.0823(12) 0.048(6) Uiso 1 1 d . . .
H3B H 0.400(4) 0.651(2) 0.0408(14) 0.059(7) Uiso 1 1 d . . .
C4 C 0.7014(5) 0.7393(2) 0.03469(17) 0.0584(7) Uani 1 1 d . . .
H4A H 0.793(4) 0.808(2) 0.0641(14) 0.054(7) Uiso 1 1 d . . .
H4B H 0.661(4) 0.7446(19) -0.0148(15) 0.060(7) Uiso 1 1 d . . .
C5 C 0.8279(5) 0.6478(2) 0.02711(15) 0.0574(6) Uani 1 1 d . . .
H5A H 0.737(4) 0.579(2) -0.0047(14) 0.065(8) Uiso 1 1 d . . .
H5B H 0.958(4) 0.664(2) 0.0056(14) 0.065(7) Uiso 1 1 d . . .
C6 C 0.8850(4) 0.63288(17) 0.10574(13) 0.0425(5) Uani 1 1 d . . .
H6 H 0.981(3) 0.6948(16) 0.1392(11) 0.034(5) Uiso 1 1 d . . .
C7 C 0.6582(3) 0.37079(16) 0.19988(12) 0.0372(5) Uani 1 1 d . . .
C8 C 0.8568(4) 0.36091(19) 0.17405(15) 0.0498(6) Uani 1 1 d . . .
H8 H 0.962(3) 0.4214(19) 0.1842(13) 0.051(6) Uiso 1 1 d . . .
C9 C 0.8870(4) 0.2588(2) 0.13229(15) 0.0548(6) Uani 1 1 d . . .
H9 H 1.023(4) 0.255(2) 0.1136(14) 0.069(8) Uiso 1 1 d . . .
C10 C 0.7241(4) 0.16609(18) 0.11606(13) 0.0517(6) Uani 1 1 d . . .
C11 C 0.5278(4) 0.17761(19) 0.14358(14) 0.0530(6) Uani 1 1 d . . .
H11 H 0.415(4) 0.115(2) 0.1336(14) 0.071(8) Uiso 1 1 d . . .
C12 C 0.4941(4) 0.27913(18) 0.18504(13) 0.0444(5) Uani 1 1 d . . .
H12 H 0.362(4) 0.2836(18) 0.2034(13) 0.056(7) Uiso 1 1 d . . .
C13 C 0.7626(5) 0.0551(2) 0.07069(18) 0.0857(10) Uani 1 1 d . . .
H13A H 0.7655 0.0523 0.0165 0.128 Uiso 1 1 calc R . .
H13B H 0.6482 -0.0021 0.0755 0.128 Uiso 1 1 calc R . .
H13C H 0.8986 0.0446 0.0912 0.128 Uiso 1 1 calc R . .
S2 S 0.25831(8) 0.96810(4) 0.24533(3) 0.04114(15) Uani 1 1 d . . .
O4 O 0.4826(2) 0.96633(11) 0.26037(10) 0.0551(4) Uani 1 1 d . . .
O5 O 0.1651(3) 0.94820(12) 0.16639(9) 0.0547(4) Uani 1 1 d . . .
O6 O 0.1795(2) 0.67462(12) 0.29645(9) 0.0435(4) Uani 1 1 d . . .
H6O H 0.253(4) 0.630(2) 0.2856(15) 0.068(9) Uiso 1 1 d . . .
F2 F -0.1399(2) 0.92558(11) 0.39910(8) 0.0690(4) Uani 1 1 d . . .
N2 N 0.1211(3) 0.87609(14) 0.27768(11) 0.0453(5) Uani 1 1 d . . .
H2N H -0.005(4) 0.8549(18) 0.2573(13) 0.047(7) Uiso 1 1 d . . .
C14 C 0.1756(3) 0.86279(17) 0.35486(13) 0.0413(5) Uani 1 1 d . . .
H14 H 0.261(3) 0.9276(16) 0.3867(11) 0.038(5) Uiso 1 1 d . . .
C15 C 0.3068(3) 0.77286(17) 0.35000(12) 0.0393(5) Uani 1 1 d . . .
H15 H 0.439(3) 0.7932(15) 0.3286(11) 0.036(5) Uiso 1 1 d . . .
C16 C 0.3548(4) 0.7567(2) 0.42974(14) 0.0492(6) Uani 1 1 d . . .
H16A H 0.450(4) 0.8259(19) 0.4644(13) 0.057(7) Uiso 1 1 d . . .
H16B H 0.439(4) 0.6975(19) 0.4237(13) 0.058(7) Uiso 1 1 d . . .
C17 C 0.1489(4) 0.7326(2) 0.46670(16) 0.0534(6) Uani 1 1 d . . .
H17A H 0.059(3) 0.6626(18) 0.4359(13) 0.049(6) Uiso 1 1 d . . .
H17B H 0.186(4) 0.7267(19) 0.5186(15) 0.062(7) Uiso 1 1 d . . .
C18 C 0.0218(5) 0.8230(2) 0.47216(15) 0.0583(7) Uani 1 1 d . . .
H18A H -0.115(4) 0.8067(19) 0.4943(14) 0.065(7) Uiso 1 1 d . . .
H18B H 0.103(4) 0.889(2) 0.5029(15) 0.071(8) Uiso 1 1 d . . .
C19 C -0.0278(4) 0.83752(17) 0.39276(13) 0.0448(5) Uani 1 1 d . . .
H19 H -0.131(3) 0.7729(16) 0.3578(11) 0.033(5) Uiso 1 1 d . . .
C20 C 0.2292(3) 1.09992(15) 0.29958(12) 0.0358(5) Uani 1 1 d . . .
C21 C 0.4018(4) 1.17227(18) 0.34832(13) 0.0455(5) Uani 1 1 d . . .
H21 H 0.528(4) 1.1495(18) 0.3562(13) 0.055(7) Uiso 1 1 d . . .
C22 C 0.3822(4) 1.27826(18) 0.38542(14) 0.0509(6) Uani 1 1 d . . .
H22 H 0.504(4) 1.327(2) 0.4174(14) 0.068(8) Uiso 1 1 d . . .
C23 C 0.1925(4) 1.31363(17) 0.37487(13) 0.0480(6) Uani 1 1 d . . .
C24 C 0.0202(4) 1.23924(19) 0.32683(14) 0.0505(6) Uani 1 1 d . . .
H24 H -0.110(4) 1.2612(18) 0.3196(13) 0.058(7) Uiso 1 1 d . . .
C25 C 0.0356(4) 1.13290(19) 0.28929(14) 0.0454(5) Uani 1 1 d . . .
H25 H -0.077(4) 1.0863(18) 0.2565(13) 0.053(7) Uiso 1 1 d . . .
C26 C 0.1764(7) 1.4308(2) 0.4136(3) 0.0755(9) Uani 1 1 d . . .
H26A H 0.292(6) 1.478(3) 0.408(2) 0.138(16) Uiso 1 1 d . . .
H26B H 0.191(6) 1.444(3) 0.466(2) 0.130(16) Uiso 1 1 d . . .
H26C H 0.047(6) 1.441(3) 0.402(2) 0.113(14) 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 1.4282(16) . ?
S1 O2 1.4357(15) . ?
S1 N1 1.5977(18) . ?
S1 C7 1.7684(19) . ?
O3 C2 1.429(2) . ?
O3 H30 0.80(2) . ?
F1 C6 1.407(2) . ?
N1 C1 1.465(3) . ?
N1 H1N 0.82(2) . ?
C1 C6 1.518(3) . ?
C1 C2 1.529(3) . ?
C1 H1 0.93(2) . ?
C2 C3 1.513(3) . ?
C2 H2 0.985(19) . ?
C3 C4 1.517(4) . ?
C3 H3A 0.94(2) . ?
C3 H3B 0.97(2) . ?
C4 C5 1.522(4) . ?
C4 H4A 0.96(2) . ?
C4 H4B 0.93(3) . ?
C5 C6 1.499(3) . ?
C5 H5A 0.97(2) . ?
C5 H5B 0.94(2) . ?
C6 H6 0.941(19) . ?
C7 C12 1.376(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.379(3) . ?
C8 H8 0.90(2) . ?
C9 C10 1.379(3) . ?
C9 H9 0.95(2) . ?
C10 C11 1.383(3) . ?
C10 C13 1.513(3) . ?
C11 C12 1.380(3) . ?
C11 H11 0.94(3) . ?
C12 H12 0.92(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
S2 O5 1.4312(16) . ?
S2 O4 1.4333(15) . ?
S2 N2 1.5965(19) . ?
S2 C20 1.7624(19) . ?
O6 C15 1.431(2) . ?
O6 H6O 0.80(3) . ?
F2 C19 1.426(2) . ?
N2 C14 1.462(3) . ?
N2 H2N 0.82(2) . ?
C14 C19 1.516(3) . ?
C14 C15 1.529(3) . ?
C14 H14 0.93(2) . ?
C15 C16 1.514(3) . ?
C15 H15 0.967(19) . ?
C16 C17 1.518(3) . ?
C16 H16A 1.00(2) . ?
C16 H16B 0.99(2) . ?
C17 C18 1.516(4) . ?
C17 H17A 0.97(2) . ?
C17 H17B 0.97(3) . ?
C18 C19 1.501(3) . ?
C18 H18A 0.98(2) . ?
C18 H18B 0.91(3) . ?
C19 H19 0.989(19) . ?
C20 C21 1.377(3) . ?
C20 C25 1.384(3) . ?
C21 C22 1.379(3) . ?
C21 H21 0.91(2) . ?
C22 C23 1.378(3) . ?
C22 H22 0.94(2) . ?
C23 C24 1.380(3) . ?
C23 C26 1.506(3) . ?
C24 C25 1.377(3) . ?
C24 H24 0.93(2) . ?
C25 H25 0.90(2) . ?
C26 H26A 0.89(4) . ?
C26 H26B 0.91(4) . ?
C26 H26C 0.87(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.43(10) . . ?
O1 S1 N1 106.66(10) . . ?
O2 S1 N1 108.10(10) . . ?
O1 S1 C7 108.98(10) . . ?
O2 S1 C7 106.18(9) . . ?
N1 S1 C7 108.15(9) . . ?
C2 O3 H30 109.4(17) . . ?
C1 N1 S1 123.19(15) . . ?
C1 N1 H1N 119.9(15) . . ?
S1 N1 H1N 113.5(15) . . ?
N1 C1 C6 110.62(17) . . ?
N1 C1 C2 111.53(16) . . ?
C6 C1 C2 110.02(17) . . ?
N1 C1 H1 108.6(12) . . ?
C6 C1 H1 108.5(12) . . ?
C2 C1 H1 107.5(12) . . ?
O3 C2 C3 111.22(18) . . ?
O3 C2 C1 105.99(16) . . ?
C3 C2 C1 111.27(18) . . ?
O3 C2 H2 108.9(11) . . ?
C3 C2 H2 111.3(11) . . ?
C1 C2 H2 108.0(11) . . ?
C2 C3 C4 111.6(2) . . ?
C2 C3 H3A 107.8(13) . . ?
C4 C3 H3A 112.7(13) . . ?
C2 C3 H3B 110.3(14) . . ?
C4 C3 H3B 109.5(14) . . ?
H3A C3 H3B 104.7(18) . . ?
C3 C4 C5 110.7(2) . . ?
C3 C4 H4A 110.2(14) . . ?
C5 C4 H4A 109.0(14) . . ?
C3 C4 H4B 109.4(15) . . ?
C5 C4 H4B 109.1(14) . . ?
H4A C4 H4B 108(2) . . ?
C6 C5 C4 110.5(2) . . ?
C6 C5 H5A 107.3(15) . . ?
C4 C5 H5A 108.8(14) . . ?
C6 C5 H5B 107.8(16) . . ?
C4 C5 H5B 111.4(15) . . ?
H5A C5 H5B 111(2) . . ?
F1 C6 C5 109.11(17) . . ?
F1 C6 C1 109.07(17) . . ?
C5 C6 C1 112.1(2) . . ?
F1 C6 H6 105.2(12) . . ?
C5 C6 H6 112.4(12) . . ?
C1 C6 H6 108.7(12) . . ?
C12 C7 C8 120.1(2) . . ?
C12 C7 S1 119.55(16) . . ?
C8 C7 S1 120.35(16) . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 121.7(14) . . ?
C7 C8 H8 119.0(14) . . ?
C10 C9 C8 121.6(2) . . ?
C10 C9 H9 120.8(15) . . ?
C8 C9 H9 117.6(15) . . ?
C9 C10 C11 118.1(2) . . ?
C9 C10 C13 120.4(2) . . ?
C11 C10 C13 121.5(2) . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.5(15) . . ?
C10 C11 H11 119.4(15) . . ?
C7 C12 C11 119.8(2) . . ?
C7 C12 H12 121.3(14) . . ?
C11 C12 H12 118.8(14) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 S2 O4 119.15(10) . . ?
O5 S2 N2 106.02(10) . . ?
O4 S2 N2 107.78(10) . . ?
O5 S2 C20 108.31(9) . . ?
O4 S2 C20 105.56(9) . . ?
N2 S2 C20 109.86(10) . . ?
C15 O6 H6O 108.7(18) . . ?
C14 N2 S2 123.10(15) . . ?
C14 N2 H2N 118.7(16) . . ?
S2 N2 H2N 113.7(16) . . ?
N2 C14 C19 110.46(18) . . ?
N2 C14 C15 111.40(17) . . ?
C19 C14 C15 110.50(17) . . ?
N2 C14 H14 109.5(12) . . ?
C19 C14 H14 108.2(12) . . ?
C15 C14 H14 106.7(12) . . ?
O6 C15 C16 111.22(18) . . ?
O6 C15 C14 106.45(16) . . ?
C16 C15 C14 110.96(18) . . ?
O6 C15 H15 108.6(11) . . ?
C16 C15 H15 110.7(12) . . ?
C14 C15 H15 108.8(11) . . ?
C15 C16 C17 111.4(2) . . ?
C15 C16 H16A 108.5(13) . . ?
C17 C16 H16A 108.7(13) . . ?
C15 C16 H16B 108.2(13) . . ?
C17 C16 H16B 112.9(13) . . ?
H16A C16 H16B 107.0(18) . . ?
C18 C17 C16 111.0(2) . . ?
C18 C17 H17A 109.3(13) . . ?
C16 C17 H17A 109.9(13) . . ?
C18 C17 H17B 109.4(14) . . ?
C16 C17 H17B 109.3(14) . . ?
H17A C17 H17B 108.0(19) . . ?
C19 C18 C17 110.4(2) . . ?
C19 C18 H18A 109.0(15) . . ?
C17 C18 H18A 111.5(14) . . ?
C19 C18 H18B 107.0(17) . . ?
C17 C18 H18B 109.9(16) . . ?
H18A C18 H18B 109(2) . . ?
F2 C19 C18 109.82(17) . . ?
F2 C19 C14 108.56(18) . . ?
C18 C19 C14 112.0(2) . . ?
F2 C19 H19 103.6(11) . . ?
C18 C19 H19 111.9(11) . . ?
C14 C19 H19 110.6(11) . . ?
C21 C20 C25 120.01(19) . . ?
C21 C20 S2 120.26(15) . . ?
C25 C20 S2 119.60(16) . . ?
C20 C21 C22 119.7(2) . . ?
C20 C21 H21 119.7(14) . . ?
C22 C21 H21 120.6(14) . . ?
C23 C22 C21 121.4(2) . . ?
C23 C22 H22 120.8(15) . . ?
C21 C22 H22 117.9(15) . . ?
C22 C23 C24 118.0(2) . . ?
C22 C23 C26 120.6(3) . . ?
C24 C23 C26 121.3(3) . . ?
C25 C24 C23 121.7(2) . . ?
C25 C24 H24 119.0(14) . . ?
C23 C24 H24 119.3(14) . . ?
C24 C25 C20 119.2(2) . . ?
C24 C25 H25 120.5(14) . . ?
C20 C25 H25 120.2(14) . . ?
C23 C26 H26A 110(2) . . ?
C23 C26 H26B 110(2) . . ?
H26A C26 H26B 101(3) . . ?
C23 C26 H26C 111(2) . . ?
H26A C26 H26C 120(3) . . ?
H26B C26 H26C 104(3) . . ?

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 C1 -172.83(15) . . . . ?
O2 S1 N1 C1 -44.46(18) . . . . ?
C7 S1 N1 C1 70.09(18) . . . . ?
S1 N1 C1 C6 -139.26(16) . . . . ?
S1 N1 C1 C2 97.95(18) . . . . ?
N1 C1 C2 O3 56.8(2) . . . . ?
C6 C1 C2 O3 -66.3(2) . . . . ?
N1 C1 C2 C3 177.86(18) . . . . ?
C6 C1 C2 C3 54.7(2) . . . . ?
O3 C2 C3 C4 62.7(3) . . . . ?
C1 C2 C3 C4 -55.3(3) . . . . ?
C2 C3 C4 C5 55.7(3) . . . . ?
C3 C4 C5 C6 -56.4(3) . . . . ?
C4 C5 C6 F1 178.4(2) . . . . ?
C4 C5 C6 C1 57.5(3) . . . . ?
N1 C1 C6 F1 59.0(2) . . . . ?
C2 C1 C6 F1 -177.36(17) . . . . ?
N1 C1 C6 C5 179.89(18) . . . . ?
C2 C1 C6 C5 -56.4(2) . . . . ?
O1 S1 C7 C12 98.40(19) . . . . ?
O2 S1 C7 C12 -30.2(2) . . . . ?
N1 S1 C7 C12 -146.03(18) . . . . ?
O1 S1 C7 C8 -79.1(2) . . . . ?
O2 S1 C7 C8 152.28(18) . . . . ?
N1 S1 C7 C8 36.5(2) . . . . ?
C12 C7 C8 C9 1.1(3) . . . . ?
S1 C7 C8 C9 178.58(18) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C8 C9 C10 C13 -179.5(2) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C13 C10 C11 C12 179.9(2) . . . . ?
C8 C7 C12 C11 -0.7(3) . . . . ?
S1 C7 C12 C11 -178.23(17) . . . . ?
C10 C11 C12 C7 -0.4(4) . . . . ?
O5 S2 N2 C14 175.19(16) . . . . ?
O4 S2 N2 C14 46.56(19) . . . . ?
C20 S2 N2 C14 -67.99(19) . . . . ?
S2 N2 C14 C19 140.00(16) . . . . ?
S2 N2 C14 C15 -96.79(19) . . . . ?
N2 C14 C15 O6 -56.6(2) . . . . ?
C19 C14 C15 O6 66.6(2) . . . . ?
N2 C14 C15 C16 -177.77(18) . . . . ?
C19 C14 C15 C16 -54.6(2) . . . . ?
O6 C15 C16 C17 -63.2(3) . . . . ?
C14 C15 C16 C17 55.1(3) . . . . ?
C15 C16 C17 C18 -56.2(3) . . . . ?
C16 C17 C18 C19 56.5(3) . . . . ?
C17 C18 C19 F2 -177.8(2) . . . . ?
C17 C18 C19 C14 -57.1(3) . . . . ?
N2 C14 C19 F2 -58.7(2) . . . . ?
C15 C14 C19 F2 177.56(16) . . . . ?
N2 C14 C19 C18 179.85(18) . . . . ?
C15 C14 C19 C18 56.1(2) . . . . ?
O5 S2 C20 C21 -133.23(17) . . . . ?
O4 S2 C20 C21 -4.6(2) . . . . ?
N2 S2 C20 C21 111.39(18) . . . . ?
O5 S2 C20 C25 42.8(2) . . . . ?
O4 S2 C20 C25 171.47(17) . . . . ?
N2 S2 C20 C25 -72.57(19) . . . . ?
C25 C20 C21 C22 -1.4(3) . . . . ?
S2 C20 C21 C22 174.63(18) . . . . ?
C20 C21 C22 C23 0.1(4) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C21 C22 C23 C26 -177.9(3) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
C26 C23 C24 C25 178.0(3) . . . . ?
C23 C24 C25 C20 -0.4(3) . . . . ?
C21 C20 C25 C24 1.5(3) . . . . ?
S2 C20 C25 C24 -174.50(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.038


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
