# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_fanxh0725_1
_audit_creation_date             2013-07-30
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H19 N O2 S'
_chemical_formula_sum            'C21 H19 N O2 S'
_chemical_formula_weight         349.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.5924(14)
_cell_length_b                   10.4758(18)
_cell_length_c                   10.797(2)
_cell_angle_alpha                97.496(15)
_cell_angle_beta                 111.360(17)
_cell_angle_gamma                90.383(14)
_cell_volume                     895.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1909
_cell_measurement_temperature    293.80(10)
_cell_measurement_theta_max      26.7220
_cell_measurement_theta_min      3.8150
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.3600
_exptl_crystal_size_mid          0.3400
_exptl_crystal_size_min          0.2800
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5643
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.19
_diffrn_ambient_temperature      293.80(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8762
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   25.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -99.0000 -120.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega   19.00   50.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700   57.0000 -120.0000 21

#__ type_ start__ end____ width___ exp.time_
  3 omega  -88.00  -17.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  -77.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00   48.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -57.0000  -30.0000 62

#__ type_ start__ end____ width___ exp.time_
  5 omega   50.00   84.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  178.0000    0.0000 23

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00   61.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075  -99.0000  120.0000 17

#__ type_ start__ end____ width___ exp.time_
  7 omega    0.00   93.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8075   57.0000  120.0000 62
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0517428000
_diffrn_orient_matrix_UB_12      -0.0538248000
_diffrn_orient_matrix_UB_13      -0.0417687000
_diffrn_orient_matrix_UB_21      0.0319318000
_diffrn_orient_matrix_UB_22      -0.0378040000
_diffrn_orient_matrix_UB_23      0.0528606000
_diffrn_orient_matrix_UB_31      -0.0647661000
_diffrn_orient_matrix_UB_32      0.0188946000
_diffrn_orient_matrix_UB_33      0.0234057000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2622
_reflns_number_total             3519
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0522P)²+0.4006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1524
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C13(H13)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C16(H16), C17(H17),
 C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.08672(9) 0.66180(7) 0.17386(7) 0.0438(2) Uani 1 1 d . . .
O1 O 0.1208(3) 0.7169(2) 0.3091(2) 0.0601(6) Uani 1 1 d . . .
O2 O -0.0796(2) 0.6088(2) 0.0908(2) 0.0527(5) Uani 1 1 d . . .
N1 N 0.2053(3) 0.5434(2) 0.1741(3) 0.0455(6) Uani 1 1 d . . .
H1 H 0.181(4) 0.496(3) 0.092(4) 0.075(11) Uiso 1 1 d . . .
C1 C 0.2960(4) 0.3454(3) 0.3886(3) 0.0425(7) Uani 1 1 d . . .
C2 C 0.1505(4) 0.3952(3) 0.4060(3) 0.0491(7) Uani 1 1 d . . .
H2 H 0.1139 0.4734 0.3773 0.059 Uiso 1 1 calc R . .
C3 C 0.0644(4) 0.3301(3) 0.4641(3) 0.0567(8) Uani 1 1 d . . .
H3 H -0.0300 0.3646 0.4750 0.068 Uiso 1 1 calc R . .
C4 C 0.1156(5) 0.2122(3) 0.5074(4) 0.0670(10) Uani 1 1 d . . .
H4 H 0.0549 0.1683 0.5461 0.080 Uiso 1 1 calc R . .
C5 C 0.2531(5) 0.1617(3) 0.4931(4) 0.0667(10) Uani 1 1 d . . .
H5 H 0.2856 0.0830 0.5224 0.080 Uiso 1 1 calc R . .
C6 C 0.3491(4) 0.2250(3) 0.4349(3) 0.0518(8) Uani 1 1 d . . .
C7 C 0.4967(5) 0.1767(3) 0.4229(4) 0.0661(10) Uani 1 1 d . . .
H7 H 0.5328 0.0997 0.4549 0.079 Uiso 1 1 calc R . .
C8 C 0.5876(4) 0.2377(3) 0.3670(4) 0.0636(9) Uani 1 1 d . . .
H8 H 0.6841 0.2027 0.3607 0.076 Uiso 1 1 calc R . .
C9 C 0.5350(4) 0.3548(3) 0.3184(3) 0.0495(7) Uani 1 1 d . . .
C10 C 0.3927(3) 0.4064(3) 0.3298(3) 0.0422(6) Uani 1 1 d . . .
C11 C 0.6054(4) 0.4396(3) 0.2527(3) 0.0571(8) Uani 1 1 d . . .
H11 H 0.7015 0.4246 0.2338 0.069 Uiso 1 1 calc R . .
C12 C 0.5139(4) 0.5414(3) 0.2233(3) 0.0536(8) Uani 1 1 d . . .
C13 C 0.3709(4) 0.5339(3) 0.2741(3) 0.0447(7) Uani 1 1 d . . .
H13 H 0.3900 0.6038 0.3487 0.054 Uiso 1 1 calc R . .
C14 C 0.5390(5) 0.6492(4) 0.1548(4) 0.0741(11) Uani 1 1 d . . .
H14A H 0.4449 0.6493 0.0723 0.111 Uiso 1 1 calc R . .
H14B H 0.6392 0.6386 0.1356 0.111 Uiso 1 1 calc R . .
H14C H 0.5491 0.7295 0.2120 0.111 Uiso 1 1 calc R . .
C15 C 0.1372(4) 0.7817(3) 0.0914(3) 0.0432(7) Uani 1 1 d U . .
C16 C 0.2148(5) 0.8974(3) 0.1620(4) 0.0649(9) Uani 1 1 d U . .
H16 H 0.2409 0.9146 0.2543 0.078 Uiso 1 1 calc R . .
C17 C 0.2540(5) 0.9891(3) 0.0937(4) 0.0754(11) Uani 1 1 d U . .
H17 H 0.3071 1.0676 0.1418 0.090 Uiso 1 1 calc R . .
C18 C 0.2167(4) 0.9672(3) -0.0417(4) 0.0637(9) Uani 1 1 d U . .
C19 C 0.1361(5) 0.8501(4) -0.1108(4) 0.0693(10) Uani 1 1 d U . .
H19 H 0.1086 0.8333 -0.2032 0.083 Uiso 1 1 calc R . .
C20 C 0.0958(4) 0.7581(3) -0.0456(3) 0.0581(8) Uani 1 1 d U . .
H20 H 0.0408 0.6803 -0.0940 0.070 Uiso 1 1 calc R . .
C21 C 0.2613(6) 1.0661(4) -0.1147(5) 0.1015(16) Uani 1 1 d U . .
H21A H 0.3510 1.0371 -0.1422 0.152 Uiso 1 1 calc R . .
H21B H 0.2959 1.1466 -0.0559 0.152 Uiso 1 1 calc R . .
H21C H 0.1654 1.0776 -0.1923 0.152 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.420(2) . ?
S1 O2 1.442(2) . ?
S1 N1 1.610(2) . ?
S1 C15 1.768(3) . ?
N1 H1 0.91(4) . ?
N1 C13 1.452(4) . ?
C1 C2 1.423(4) . ?
C1 C6 1.433(4) . ?
C1 C10 1.409(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.360(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.349(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.413(5) . ?
C6 C7 1.411(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.348(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.410(4) . ?
C9 C10 1.380(4) . ?
C9 C11 1.459(4) . ?
C10 C13 1.521(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.331(4) . ?
C12 C13 1.522(4) . ?
C12 C14 1.484(4) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.369(4) . ?
C15 C20 1.377(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.365(5) . ?
C18 C19 1.383(5) . ?
C18 C21 1.506(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(4) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.61(13) . . ?
O1 S1 N1 108.35(13) . . ?
O1 S1 C15 107.66(14) . . ?
O2 S1 N1 104.70(13) . . ?
O2 S1 C15 106.98(13) . . ?
N1 S1 C15 109.23(13) . . ?
S1 N1 H1 114(2) . . ?
C13 N1 S1 125.6(2) . . ?
C13 N1 H1 117(2) . . ?
C2 C1 C6 117.9(3) . . ?
C10 C1 C2 124.7(3) . . ?
C10 C1 C6 117.4(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.8(3) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 118.3(3) . . ?
C7 C6 C1 118.6(3) . . ?
C7 C6 C5 123.1(3) . . ?
C6 C7 H7 118.6 . . ?
C8 C7 C6 122.7(3) . . ?
C8 C7 H7 118.6 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C11 131.4(3) . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 C11 108.8(3) . . ?
C1 C10 C13 129.8(2) . . ?
C9 C10 C1 122.1(3) . . ?
C9 C10 C13 108.1(3) . . ?
C9 C11 H11 124.4 . . ?
C12 C11 C9 111.1(3) . . ?
C12 C11 H11 124.4 . . ?
C11 C12 C13 108.8(3) . . ?
C11 C12 C14 128.7(3) . . ?
C14 C12 C13 122.5(3) . . ?
N1 C13 C10 113.3(2) . . ?
N1 C13 C12 114.9(2) . . ?
N1 C13 H13 108.4 . . ?
C10 C13 C12 103.1(2) . . ?
C10 C13 H13 108.4 . . ?
C12 C13 H13 108.4 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 S1 120.7(2) . . ?
C16 C15 C20 120.1(3) . . ?
C20 C15 S1 119.3(2) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(3) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 C19 117.7(3) . . ?
C17 C18 C21 121.7(4) . . ?
C19 C18 C21 120.6(4) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.4(3) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
S1 N1 C13 C10 129.9(2) . . . . ?
S1 N1 C13 C12 -111.9(3) . . . . ?
S1 C15 C16 C17 179.4(3) . . . . ?
S1 C15 C20 C19 -179.3(3) . . . . ?
O1 S1 N1 C13 -30.3(3) . . . . ?
O1 S1 C15 C16 7.3(3) . . . . ?
O1 S1 C15 C20 -171.9(2) . . . . ?
O2 S1 N1 C13 -159.0(2) . . . . ?
O2 S1 C15 C16 137.1(3) . . . . ?
O2 S1 C15 C20 -42.1(3) . . . . ?
N1 S1 C15 C16 -110.1(3) . . . . ?
N1 S1 C15 C20 70.7(3) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C1 C6 C7 C8 -1.5(5) . . . . ?
C1 C10 C13 N1 -53.9(4) . . . . ?
C1 C10 C13 C12 -178.8(3) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
C2 C1 C6 C7 -177.7(3) . . . . ?
C2 C1 C10 C9 178.5(3) . . . . ?
C2 C1 C10 C13 0.7(5) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C4 C5 C6 C7 177.7(4) . . . . ?
C5 C6 C7 C8 179.9(4) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C6 C1 C10 C9 -1.1(4) . . . . ?
C6 C1 C10 C13 -178.9(3) . . . . ?
C6 C7 C8 C9 0.2(6) . . . . ?
C7 C8 C9 C10 0.8(5) . . . . ?
C7 C8 C9 C11 -179.1(3) . . . . ?
C8 C9 C10 C1 -0.3(5) . . . . ?
C8 C9 C10 C13 177.9(3) . . . . ?
C8 C9 C11 C12 -180.0(3) . . . . ?
C9 C10 C13 N1 128.0(3) . . . . ?
C9 C10 C13 C12 3.2(3) . . . . ?
C9 C11 C12 C13 1.9(4) . . . . ?
C9 C11 C12 C14 -178.8(3) . . . . ?
C10 C1 C2 C3 -179.9(3) . . . . ?
C10 C1 C6 C5 -179.5(3) . . . . ?
C10 C1 C6 C7 1.9(4) . . . . ?
C10 C9 C11 C12 0.2(4) . . . . ?
C11 C9 C10 C1 179.6(3) . . . . ?
C11 C9 C10 C13 -2.2(3) . . . . ?
C11 C12 C13 N1 -126.8(3) . . . . ?
C11 C12 C13 C10 -3.1(3) . . . . ?
C14 C12 C13 N1 53.9(4) . . . . ?
C14 C12 C13 C10 177.6(3) . . . . ?
C15 S1 N1 C13 86.7(2) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
C16 C15 C20 C19 1.5(5) . . . . ?
C16 C17 C18 C19 0.7(6) . . . . ?
C16 C17 C18 C21 -179.2(3) . . . . ?
C17 C18 C19 C20 -0.5(6) . . . . ?
C18 C19 C20 C15 -0.5(6) . . . . ?
C20 C15 C16 C17 -1.4(5) . . . . ?
C21 C18 C19 C20 179.4(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 965332'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_fanxh0802
_audit_creation_date             2013-08-02
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H19 N O2 S'
_chemical_formula_sum            'C21 H19 N O2 S'
_chemical_formula_weight         349.43
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   10.2086(5)
_cell_length_b                   7.3342(6)
_cell_length_c                   23.4547(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1756.09(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1069
_cell_measurement_temperature    301.19(10)
_cell_measurement_theta_max      24.6620
_cell_measurement_theta_min      3.8230
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4431
_diffrn_reflns_point_group_measured_fraction_full 0.690
_diffrn_reflns_point_group_measured_fraction_max 0.686
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.420
_diffrn_ambient_temperature      301.19(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9962
_diffrn_measured_fraction_theta_max 0.6027
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00   93.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  178.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega   37.00   73.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   38.0000 -150.0000 24

#__ type_ start__ end____ width___ exp.time_
  3 omega  -35.00   35.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000  -90.0000 47
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0019727000
_diffrn_orient_matrix_UB_12      -0.0023889000
_diffrn_orient_matrix_UB_13      -0.0302195000
_diffrn_orient_matrix_UB_21      -0.0595286000
_diffrn_orient_matrix_UB_22      -0.0496444000
_diffrn_orient_matrix_UB_23      0.0011092000
_diffrn_orient_matrix_UB_31      -0.0357436000
_diffrn_orient_matrix_UB_32      0.0828884000
_diffrn_orient_matrix_UB_33      -0.0001900000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.339
_reflns_Friedel_fraction_full    0.366
_reflns_Friedel_fraction_max     0.356
_reflns_number_gt                1700
_reflns_number_total             2372
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 377 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.15(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0238P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C17(H17), C20(H20), C4(H4), C1(H1), C2(H2), C7(H7),
 C8(H8), C3(H3A)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.22796(12) -0.22185(15) -0.66493(6) 0.0435(3) Uani 1 1 d . . . . .
O2 O -0.1522(4) -0.0784(4) -0.68994(14) 0.0587(11) Uani 1 1 d . . . . .
O1 O -0.3616(3) -0.1900(4) -0.64797(15) 0.0559(11) Uani 1 1 d . . . . .
C15 C -0.2287(5) -0.4099(7) -0.7118(2) 0.0402(12) Uani 1 1 d . . . . .
C16 C -0.3243(5) -0.5423(7) -0.7056(2) 0.0486(14) Uani 1 1 d . . . . .
H16 H -0.3916 -0.5271 -0.6793 0.058 Uiso 1 1 calc R U . . .
C19 C -0.1270(6) -0.5891(8) -0.7839(2) 0.0571(16) Uani 1 1 d . . . . .
H19 H -0.0610 -0.6034 -0.8109 0.069 Uiso 1 1 calc R U . . .
C17 C -0.3184(6) -0.6972(8) -0.7390(2) 0.0559(15) Uani 1 1 d . . . . .
H17 H -0.3833 -0.7854 -0.7350 0.067 Uiso 1 1 calc R U . . .
C20 C -0.1296(5) -0.4325(7) -0.7511(2) 0.0478(14) Uani 1 1 d . . . . .
H20 H -0.0654 -0.3437 -0.7554 0.057 Uiso 1 1 calc R U . . .
C5 C -0.4925(5) -0.4460(8) -0.4481(2) 0.0438(13) Uani 1 1 d . . . . .
C13 C -0.1952(5) -0.4312(7) -0.5740(2) 0.0378(12) Uani 1 1 d . . . . .
C10 C -0.3199(5) -0.5763(6) -0.5057(2) 0.0375(12) Uani 1 1 d . . . . .
C18 C -0.2197(6) -0.7249(8) -0.7778(2) 0.0461(15) Uani 1 1 d . . . . .
C11 C -0.2276(5) -0.7137(7) -0.5309(2) 0.0404(14) Uani 1 1 d . . . . .
H11A H -0.2752 -0.8139 -0.5482 0.048 Uiso 1 1 calc R U . . .
H11B H -0.1687 -0.7618 -0.5022 0.048 Uiso 1 1 calc R U . . .
N3 N -0.1475(5) -0.2840(6) -0.60763(18) 0.0400(11) Uani 1 1 d . . . . .
C12 C -0.1532(5) -0.6056(7) -0.5754(2) 0.0376(12) Uani 1 1 d . . . . .
C6 C -0.4159(5) -0.6000(7) -0.4633(2) 0.0413(13) Uani 1 1 d . . . . .
C14 C -0.0521(5) -0.6910(7) -0.6129(2) 0.0492(14) Uani 1 1 d . . . . .
H14A H -0.0933 -0.7777 -0.6378 0.074 Uiso 1 1 calc R U . . .
H14B H 0.0119 -0.7520 -0.5898 0.074 Uiso 1 1 calc R U . . .
H14C H -0.0101 -0.5983 -0.6352 0.074 Uiso 1 1 calc R U . . .
C9 C -0.3002(5) -0.4096(6) -0.53120(19) 0.0371(12) Uani 1 1 d . . . . .
C4 C -0.5928(6) -0.4685(9) -0.4061(2) 0.0601(16) Uani 1 1 d . . . . .
H4 H -0.6456 -0.3699 -0.3965 0.072 Uiso 1 1 calc R U . . .
C1 C -0.4400(5) -0.7672(7) -0.4352(2) 0.0535(15) Uani 1 1 d . . . . .
H1 H -0.3899 -0.8690 -0.4442 0.064 Uiso 1 1 calc R U . . .
C2 C -0.5364(6) -0.7810(9) -0.3949(3) 0.0669(19) Uani 1 1 d . . . . .
H2 H -0.5514 -0.8924 -0.3771 0.080 Uiso 1 1 calc R U . . .
C7 C -0.4690(6) -0.2768(8) -0.4746(2) 0.0554(16) Uani 1 1 d . . . . .
H7 H -0.5197 -0.1768 -0.4641 0.066 Uiso 1 1 calc R U . . .
C21 C -0.2105(7) -0.8963(7) -0.8135(2) 0.0703(19) Uani 1 1 d . . . . .
H21A H -0.2113 -0.8643 -0.8532 0.105 Uiso 1 1 calc R U . . .
H21B H -0.2838 -0.9740 -0.8053 0.105 Uiso 1 1 calc R U . . .
H21C H -0.1306 -0.9593 -0.8047 0.105 Uiso 1 1 calc R U . . .
C8 C -0.3743(5) -0.2548(6) -0.5150(2) 0.0463(14) Uani 1 1 d . . . . .
H8 H -0.3588 -0.1414 -0.5314 0.056 Uiso 1 1 calc R U . . .
C3 C -0.6122(7) -0.6313(11) -0.3801(2) 0.0693(19) Uani 1 1 d . . . . .
H3A H -0.6764 -0.6426 -0.3522 0.083 Uiso 1 1 calc R U . . .
H3 H -0.065(5) -0.290(6) -0.6143(19) 0.040(15) 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 1.432(3) . ?
S1 O1 1.440(3) . ?
S1 C15 1.763(5) . ?
S1 N3 1.639(4) . ?
C15 C16 1.385(6) . ?
C15 C20 1.378(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.384(7) . ?
C19 C18 1.382(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(8) . ?
C20 H20 0.9300 . ?
C5 C6 1.419(7) . ?
C5 C4 1.430(7) . ?
C5 C7 1.408(7) . ?
C13 N3 1.424(6) . ?
C13 C12 1.350(6) . ?
C13 C9 1.476(6) . ?
C10 C11 1.501(6) . ?
C10 C6 1.408(6) . ?
C10 C9 1.376(6) . ?
C18 C21 1.514(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.514(7) . ?
N3 H3 0.86(5) . ?
C12 C14 1.493(7) . ?
C6 C1 1.414(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C9 C8 1.416(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.355(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.369(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(7) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C8 H8 0.9300 . ?
C3 H3A 0.9300 . ?

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 120.4(2) . . ?
O2 S1 C15 108.8(2) . . ?
O2 S1 N3 105.6(2) . . ?
O1 S1 C15 107.2(2) . . ?
O1 S1 N3 107.1(2) . . ?
N3 S1 C15 107.2(2) . . ?
C16 C15 S1 119.0(4) . . ?
C20 C15 S1 120.5(4) . . ?
C20 C15 C16 120.2(5) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.1(5) . . ?
C17 C16 H16 120.4 . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.8(5) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(6) . . ?
C18 C17 H17 119.0 . . ?
C15 C20 C19 119.1(5) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C6 C5 C4 118.4(5) . . ?
C7 C5 C6 119.8(5) . . ?
C7 C5 C4 121.8(6) . . ?
N3 C13 C9 122.9(4) . . ?
C12 C13 N3 126.6(5) . . ?
C12 C13 C9 110.5(4) . . ?
C6 C10 C11 129.2(4) . . ?
C9 C10 C11 109.5(4) . . ?
C9 C10 C6 121.3(5) . . ?
C19 C18 C21 119.9(5) . . ?
C17 C18 C19 117.7(5) . . ?
C17 C18 C21 122.4(6) . . ?
C10 C11 H11A 111.0 . . ?
C10 C11 H11B 111.0 . . ?
C10 C11 C12 103.6(4) . . ?
H11A C11 H11B 109.0 . . ?
C12 C11 H11A 111.0 . . ?
C12 C11 H11B 111.0 . . ?
S1 N3 H3 111(3) . . ?
C13 N3 S1 119.6(4) . . ?
C13 N3 H3 113(3) . . ?
C13 C12 C11 108.6(4) . . ?
C13 C12 C14 129.2(5) . . ?
C14 C12 C11 122.2(4) . . ?
C10 C6 C5 117.6(5) . . ?
C10 C6 C1 123.9(5) . . ?
C1 C6 C5 118.5(5) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C9 C13 107.8(4) . . ?
C10 C9 C8 121.2(4) . . ?
C8 C9 C13 131.0(5) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 C5 121.1(6) . . ?
C3 C4 H4 119.4 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.8(6) . . ?
C2 C1 H1 119.6 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(6) . . ?
C3 C2 H2 119.5 . . ?
C5 C7 H7 119.0 . . ?
C8 C7 C5 122.1(5) . . ?
C8 C7 H7 119.0 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 C8 H8 121.0 . . ?
C7 C8 C9 118.1(5) . . ?
C7 C8 H8 121.0 . . ?
C4 C3 C2 120.2(6) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?

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
S1 C15 C16 C17 -174.5(4) . . . . ?
S1 C15 C20 C19 174.6(4) . . . . ?
O2 S1 C15 C16 -161.1(4) . . . . ?
O2 S1 C15 C20 24.0(5) . . . . ?
O2 S1 N3 C13 -177.5(4) . . . . ?
O1 S1 C15 C16 -29.5(5) . . . . ?
O1 S1 C15 C20 155.6(4) . . . . ?
O1 S1 N3 C13 53.1(4) . . . . ?
C15 S1 N3 C13 -61.6(4) . . . . ?
C15 C16 C17 C18 0.7(8) . . . . ?
C16 C15 C20 C19 -0.2(7) . . . . ?
C16 C17 C18 C19 -1.9(8) . . . . ?
C16 C17 C18 C21 178.4(5) . . . . ?
C20 C15 C16 C17 0.4(8) . . . . ?
C20 C19 C18 C17 2.1(8) . . . . ?
C20 C19 C18 C21 -178.2(5) . . . . ?
C5 C6 C1 C2 0.9(8) . . . . ?
C5 C4 C3 C2 -1.6(9) . . . . ?
C5 C7 C8 C9 1.4(8) . . . . ?
C13 C9 C8 C7 178.2(5) . . . . ?
C10 C11 C12 C13 1.7(5) . . . . ?
C10 C11 C12 C14 -178.0(4) . . . . ?
C10 C6 C1 C2 -179.1(5) . . . . ?
C10 C9 C8 C7 -2.1(7) . . . . ?
C18 C19 C20 C15 -1.1(8) . . . . ?
C11 C10 C6 C5 -178.6(5) . . . . ?
C11 C10 C6 C1 1.4(8) . . . . ?
C11 C10 C9 C13 0.2(6) . . . . ?
C11 C10 C9 C8 -179.6(4) . . . . ?
N3 S1 C15 C16 85.1(5) . . . . ?
N3 S1 C15 C20 -89.8(4) . . . . ?
N3 C13 C12 C11 177.8(5) . . . . ?
N3 C13 C12 C14 -2.5(9) . . . . ?
N3 C13 C9 C10 -178.6(4) . . . . ?
N3 C13 C9 C8 1.2(8) . . . . ?
C12 C13 N3 S1 98.9(6) . . . . ?
C12 C13 C9 C10 0.9(6) . . . . ?
C12 C13 C9 C8 -179.3(5) . . . . ?
C6 C5 C4 C3 1.9(8) . . . . ?
C6 C5 C7 C8 0.2(8) . . . . ?
C6 C10 C11 C12 178.2(5) . . . . ?
C6 C10 C9 C13 -179.1(4) . . . . ?
C6 C10 C9 C8 1.1(7) . . . . ?
C6 C1 C2 C3 -0.6(9) . . . . ?
C9 C13 N3 S1 -81.7(5) . . . . ?
C9 C13 C12 C11 -1.6(6) . . . . ?
C9 C13 C12 C14 178.0(5) . . . . ?
C9 C10 C11 C12 -1.1(6) . . . . ?
C9 C10 C6 C5 0.6(7) . . . . ?
C9 C10 C6 C1 -179.4(5) . . . . ?
C4 C5 C6 C10 178.4(5) . . . . ?
C4 C5 C6 C1 -1.5(7) . . . . ?
C4 C5 C7 C8 -179.4(5) . . . . ?
C1 C2 C3 C4 0.9(10) . . . . ?
C7 C5 C6 C10 -1.3(7) . . . . ?
C7 C5 C6 C1 178.8(5) . . . . ?
C7 C5 C4 C3 -178.4(6) . . . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-2
_database_code_depnum_ccdc_archive 'CCDC 965333'
