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

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#                                CCDC 
# 
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# 
#  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.
#
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#  fide research purposes only. It may contain copyright material
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data_tang20
_audit_creation_date             2014-05-22
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H22 N2 O2 S'
_chemical_formula_sum            'C25 H22 N2 O2 S'
_chemical_formula_weight         414.50
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.247(3)
_cell_length_b                   11.312(3)
_cell_length_c                   14.218(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.780(16)
_cell_angle_gamma                90
_cell_volume                     2005.0(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9673
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.316
_cell_measurement_theta_min      2.357
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0908 before and 0.0351 after correction.
The Ratio of minimum to maximum transmission is 0.9442.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.41
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            48251
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         1.817
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.5\ ω and 0.5\ φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4730
_reflns_number_total             4971
_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       'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 Ver. 2014.1-1 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²+1.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1014
_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:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C20(H20), C21(H21), C22(H22), C23(H23), C25(H25)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.52035(2) 0.29069(2) 0.78214(2) 0.01603(9) Uani 1 1 d . . . . .
O1 O 0.44265(7) 0.33996(8) 0.82083(6) 0.02049(18) Uani 1 1 d . . . . .
O2 O 0.61237(7) 0.23232(8) 0.84898(6) 0.02152(19) Uani 1 1 d . . . . .
N1 N 0.56725(8) 0.40224(9) 0.73236(7) 0.01715(19) Uani 1 1 d . . . . .
N2 N 0.49416(9) 0.68342(10) 0.95821(8) 0.0210(2) Uani 1 1 d . . . . .
H2 H 0.5253(14) 0.6801(16) 1.0233(14) 0.030(4) Uiso 1 1 d . . . . .
C1 C 0.45424(9) 0.19433(10) 0.68463(8) 0.0156(2) Uani 1 1 d . . . . .
C2 C 0.50690(9) 0.09301(11) 0.67114(9) 0.0185(2) Uani 1 1 d . . . . .
H2A H 0.5784 0.0772 0.7130 0.022 Uiso 1 1 calc R . . . .
C3 C 0.45290(10) 0.01533(11) 0.59517(9) 0.0207(2) Uani 1 1 d . . . . .
H3 H 0.4880 -0.0545 0.5854 0.025 Uiso 1 1 calc R . . . .
C4 C 0.34810(10) 0.03801(11) 0.53291(9) 0.0203(2) Uani 1 1 d . . . . .
C5 C 0.29708(10) 0.14071(11) 0.54865(9) 0.0208(2) Uani 1 1 d . . . . .
H5 H 0.2258 0.1571 0.5065 0.025 Uiso 1 1 calc R . . . .
C6 C 0.34886(9) 0.21879(10) 0.62462(9) 0.0187(2) Uani 1 1 d . . . . .
H6 H 0.3134 0.2876 0.6357 0.022 Uiso 1 1 calc R . . . .
C7 C 0.28982(11) -0.04818(13) 0.45212(11) 0.0298(3) Uani 1 1 d . . . . .
H7A H 0.3389 -0.1116 0.4488 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.2636 -0.0070 0.3877 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.2290 -0.0821 0.4673 0.045 Uiso 1 1 calc GR . . . .
C8 C 0.65620(9) 0.38872(10) 0.69891(9) 0.0178(2) Uani 1 1 d . . . . .
C9 C 0.73595(10) 0.30236(11) 0.72069(10) 0.0219(2) Uani 1 1 d . . . . .
H9 H 0.7364 0.2376 0.7633 0.026 Uiso 1 1 calc R . . . .
C10 C 0.81499(10) 0.31541(12) 0.67709(11) 0.0256(3) Uani 1 1 d . . . . .
H10 H 0.8706 0.2582 0.6903 0.031 Uiso 1 1 calc R . . . .
C11 C 0.81451(10) 0.41062(13) 0.61437(11) 0.0267(3) Uani 1 1 d . . . . .
H11 H 0.8696 0.4170 0.5859 0.032 Uiso 1 1 calc R . . . .
C12 C 0.73478(10) 0.49592(12) 0.59309(10) 0.0235(3) Uani 1 1 d . . . . .
H12 H 0.7347 0.5606 0.5504 0.028 Uiso 1 1 calc R . . . .
C13 C 0.65440(9) 0.48462(10) 0.63584(9) 0.0184(2) Uani 1 1 d . . . . .
C14 C 0.56187(9) 0.55648(10) 0.62834(8) 0.0180(2) Uani 1 1 d . . . . .
C15 C 0.53323(11) 0.66910(11) 0.57007(10) 0.0235(2) Uani 1 1 d . . . . .
H15A H 0.5893 0.7281 0.5990 0.035 Uiso 1 1 calc GR . . . .
H15B H 0.4647 0.6986 0.5727 0.035 Uiso 1 1 calc GR . . . .
H15C H 0.5269 0.6543 0.5004 0.035 Uiso 1 1 calc GR . . . .
C16 C 0.50923(9) 0.50547(10) 0.68475(8) 0.0169(2) Uani 1 1 d . . . . .
C17 C 0.41144(9) 0.55137(11) 0.70312(9) 0.0184(2) Uani 1 1 d . . . . .
H17A H 0.3657 0.4835 0.7065 0.022 Uiso 1 1 calc R . . . .
H17B H 0.3701 0.6007 0.6455 0.022 Uiso 1 1 calc R . . . .
C18 C 0.43458(9) 0.62353(10) 0.79740(9) 0.0178(2) Uani 1 1 d . . . . .
C19 C 0.39894(9) 0.74262(11) 0.80243(9) 0.0180(2) Uani 1 1 d . . . . .
C20 C 0.33922(10) 0.82427(11) 0.73120(10) 0.0217(2) Uani 1 1 d . . . . .
H20 H 0.3119 0.8035 0.6624 0.026 Uiso 1 1 calc R . . . .
C21 C 0.32046(11) 0.93557(12) 0.76229(10) 0.0248(3) Uani 1 1 d . . . . .
H21 H 0.2813 0.9919 0.7142 0.030 Uiso 1 1 calc R . . . .
C22 C 0.35854(10) 0.96638(11) 0.86402(10) 0.0250(3) Uani 1 1 d . . . . .
H22 H 0.3442 1.0432 0.8834 0.030 Uiso 1 1 calc R . . . .
C23 C 0.41628(10) 0.88759(11) 0.93650(10) 0.0218(2) Uani 1 1 d . . . . .
H23 H 0.4410 0.9082 1.0053 0.026 Uiso 1 1 calc R . . . .
C24 C 0.43684(9) 0.77648(11) 0.90436(9) 0.0187(2) Uani 1 1 d . . . . .
C25 C 0.49202(10) 0.59173(11) 0.89363(9) 0.0201(2) Uani 1 1 d . . . . .
H25 H 0.5256 0.5172 0.9131 0.024 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 1.4339(9) . ?
S1 O2 1.4287(9) . ?
S1 N1 1.6664(11) . ?
S1 C1 1.7480(12) . ?
N1 C8 1.4204(15) . ?
N1 C16 1.4354(15) . ?
N2 H2 0.877(18) . ?
N2 C24 1.3703(16) . ?
N2 C25 1.3793(16) . ?
C1 C2 1.3885(16) . ?
C1 C6 1.3954(16) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3884(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3947(17) . ?
C4 C5 1.3997(18) . ?
C4 C7 1.5054(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3842(17) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.3947(17) . ?
C8 C13 1.4026(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3935(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.397(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3863(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.3992(17) . ?
C13 C14 1.4444(16) . ?
C14 C15 1.4969(17) . ?
C14 C16 1.3569(16) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.4984(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5096(16) . ?
C18 C19 1.4373(16) . ?
C18 C25 1.3696(17) . ?
C19 C20 1.4009(17) . ?
C19 C24 1.4165(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.3846(18) . ?
C21 H21 0.9500 . ?
C21 C22 1.405(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.3814(19) . ?
C23 H23 0.9500 . ?
C23 C24 1.3954(17) . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 106.72(5) . . ?
O1 S1 C1 108.34(6) . . ?
O2 S1 O1 119.08(6) . . ?
O2 S1 N1 106.01(6) . . ?
O2 S1 C1 108.97(6) . . ?
N1 S1 C1 107.11(5) . . ?
C8 N1 S1 122.10(8) . . ?
C8 N1 C16 107.59(9) . . ?
C16 N1 S1 126.82(8) . . ?
C24 N2 H2 126.6(12) . . ?
C24 N2 C25 108.85(11) . . ?
C25 N2 H2 124.5(12) . . ?
C2 C1 S1 118.95(9) . . ?
C2 C1 C6 121.65(11) . . ?
C6 C1 S1 119.36(9) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 C1 118.64(11) . . ?
C3 C2 H2A 120.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.16(11) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 118.82(11) . . ?
C3 C4 C7 120.56(12) . . ?
C5 C4 C7 120.59(11) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.05(11) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 120.7 . . ?
C5 C6 C1 118.66(11) . . ?
C5 C6 H6 120.7 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N1 130.77(11) . . ?
C9 C8 C13 122.11(11) . . ?
C13 C8 N1 107.11(10) . . ?
C8 C9 H9 121.5 . . ?
C10 C9 C8 116.99(12) . . ?
C10 C9 H9 121.5 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.59(12) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.97(12) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.50(12) . . ?
C13 C12 H12 120.7 . . ?
C8 C13 C14 108.24(10) . . ?
C12 C13 C8 119.84(11) . . ?
C12 C13 C14 131.92(12) . . ?
C13 C14 C15 124.73(11) . . ?
C16 C14 C13 108.06(11) . . ?
C16 C14 C15 127.18(11) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 123.79(10) . . ?
C14 C16 N1 108.94(10) . . ?
C14 C16 C17 127.10(11) . . ?
C16 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C16 C17 C18 114.48(10) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C19 C18 C17 125.42(11) . . ?
C25 C18 C17 128.48(11) . . ?
C25 C18 C19 106.10(10) . . ?
C20 C19 C18 134.16(12) . . ?
C20 C19 C24 118.64(11) . . ?
C24 C19 C18 107.20(10) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.16(12) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 120.91(12) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.54(12) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 H23 121.4 . . ?
C22 C23 C24 117.20(12) . . ?
C24 C23 H23 121.4 . . ?
N2 C24 C19 107.55(10) . . ?
N2 C24 C23 129.91(12) . . ?
C23 C24 C19 122.53(11) . . ?
N2 C25 H25 124.9 . . ?
C18 C25 N2 110.29(11) . . ?
C18 C25 H25 124.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.877(18) 2.123(19) 2.9766(16) 164.2(16) 3_667

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 C8 C9 -18.46(17) . . . . ?
S1 N1 C8 C13 162.66(8) . . . . ?
S1 N1 C16 C14 -161.64(9) . . . . ?
S1 N1 C16 C17 22.74(16) . . . . ?
S1 C1 C2 C3 178.36(9) . . . . ?
S1 C1 C6 C5 -179.06(9) . . . . ?
O1 S1 N1 C8 171.33(9) . . . . ?
O1 S1 N1 C16 -32.44(11) . . . . ?
O1 S1 C1 C2 -145.08(9) . . . . ?
O1 S1 C1 C6 32.69(11) . . . . ?
O2 S1 N1 C8 43.43(10) . . . . ?
O2 S1 N1 C16 -160.33(9) . . . . ?
O2 S1 C1 C2 -14.13(11) . . . . ?
O2 S1 C1 C6 163.64(9) . . . . ?
N1 S1 C1 C2 100.13(10) . . . . ?
N1 S1 C1 C6 -82.10(10) . . . . ?
N1 C8 C9 C10 -178.53(12) . . . . ?
N1 C8 C13 C12 178.66(10) . . . . ?
N1 C8 C13 C14 -1.42(12) . . . . ?
N1 C16 C17 C18 80.51(14) . . . . ?
C1 S1 N1 C8 -72.81(10) . . . . ?
C1 S1 N1 C16 83.42(11) . . . . ?
C1 C2 C3 C4 0.32(18) . . . . ?
C2 C1 C6 C5 -1.35(18) . . . . ?
C2 C3 C4 C5 -0.55(18) . . . . ?
C2 C3 C4 C7 -178.82(12) . . . . ?
C3 C4 C5 C6 -0.19(19) . . . . ?
C4 C5 C6 C1 1.11(18) . . . . ?
C6 C1 C2 C3 0.64(18) . . . . ?
C7 C4 C5 C6 178.08(12) . . . . ?
C8 N1 C16 C14 -2.63(13) . . . . ?
C8 N1 C16 C17 -178.24(10) . . . . ?
C8 C9 C10 C11 -0.01(19) . . . . ?
C8 C13 C14 C15 178.20(11) . . . . ?
C8 C13 C14 C16 -0.20(13) . . . . ?
C9 C8 C13 C12 -0.34(18) . . . . ?
C9 C8 C13 C14 179.58(11) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C11 C12 C13 -0.05(19) . . . . ?
C11 C12 C13 C8 0.25(18) . . . . ?
C11 C12 C13 C14 -179.65(12) . . . . ?
C12 C13 C14 C15 -1.9(2) . . . . ?
C12 C13 C14 C16 179.71(12) . . . . ?
C13 C8 C9 C10 0.21(18) . . . . ?
C13 C14 C16 N1 1.73(13) . . . . ?
C13 C14 C16 C17 177.17(11) . . . . ?
C14 C16 C17 C18 -94.30(14) . . . . ?
C15 C14 C16 N1 -176.62(11) . . . . ?
C15 C14 C16 C17 -1.2(2) . . . . ?
C16 N1 C8 C9 -178.67(12) . . . . ?
C16 N1 C8 C13 2.44(12) . . . . ?
C16 C17 C18 C19 123.67(12) . . . . ?
C16 C17 C18 C25 -56.27(17) . . . . ?
C17 C18 C19 C20 -0.9(2) . . . . ?
C17 C18 C19 C24 179.35(11) . . . . ?
C17 C18 C25 N2 -179.92(11) . . . . ?
C18 C19 C20 C21 -178.79(12) . . . . ?
C18 C19 C24 N2 1.01(13) . . . . ?
C18 C19 C24 C23 -179.74(11) . . . . ?
C19 C18 C25 N2 0.13(14) . . . . ?
C19 C20 C21 C22 -1.32(19) . . . . ?
C20 C19 C24 N2 -178.77(10) . . . . ?
C20 C19 C24 C23 0.49(17) . . . . ?
C20 C21 C22 C23 0.3(2) . . . . ?
C21 C22 C23 C24 1.02(18) . . . . ?
C22 C23 C24 N2 177.63(12) . . . . ?
C22 C23 C24 C19 -1.44(18) . . . . ?
C24 N2 C25 C18 0.51(14) . . . . ?
C24 C19 C20 C21 0.91(17) . . . . ?
C25 N2 C24 C19 -0.94(13) . . . . ?
C25 N2 C24 C23 179.88(12) . . . . ?
C25 C18 C19 C20 179.03(13) . . . . ?
C25 C18 C19 C24 -0.69(13) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1016687'
#######################################################################
#
#                 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_tang21
_audit_creation_date             2014-05-22
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C31 H26 N2 O2 S'
_chemical_formula_sum            'C31 H26 N2 O2 S'
_chemical_formula_weight         490.60
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.1262(11)
_cell_length_b                   9.3818(5)
_cell_length_c                   20.2526(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.247(5)
_cell_angle_gamma                90
_cell_volume                     2549.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9384
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.88
_cell_measurement_theta_min      3.294
_shelx_estimated_absorpt_T_max   0.584
_shelx_estimated_absorpt_T_min   0.514
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.6746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0430 before and 0.0295 after correction.
The Ratio of minimum to maximum transmission is 0.8951.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.44
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            46397
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         72.995
_diffrn_reflns_theta_min         3.294
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.7 φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'equatorially mounted graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, K FFCU 2K 90'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4978
_reflns_number_total             4996
_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       'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 Ver. 2014.1-1 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4996
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+1.3787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0893
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C26(H26), C27(H27), C28(H28),
  C29(H29), C31(H31)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.73663(2) 0.53993(3) 0.63188(2) 0.01513(9) Uani 1 1 d . . . . .
O1 O 0.80592(7) 0.58732(10) 0.69612(5) 0.0232(2) Uani 1 1 d . . . . .
O2 O 0.63533(6) 0.58877(9) 0.61187(5) 0.01966(19) Uani 1 1 d . . . . .
N1 N 0.72560(8) 0.36700(11) 0.63358(5) 0.0161(2) Uani 1 1 d . . . . .
H1 H 0.6676(12) 0.3411(17) 0.6097(8) 0.019 Uiso 1 1 d R . . . .
N2 N 0.57538(8) 0.31144(12) 0.40334(6) 0.0211(2) Uani 1 1 d . . . . .
H2 H 0.5264(13) 0.3537(18) 0.3736(9) 0.025 Uiso 1 1 d R . . . .
C1 C 0.78778(9) 0.57984(13) 0.56543(6) 0.0174(2) Uani 1 1 d . . . . .
C2 C 0.72587(10) 0.57753(13) 0.49673(7) 0.0207(3) Uani 1 1 d . . . . .
H2A H 0.6570 0.5560 0.4861 0.025 Uiso 1 1 calc R . . . .
C3 C 0.76602(11) 0.60706(14) 0.44420(7) 0.0256(3) Uani 1 1 d . . . . .
H3 H 0.7242 0.6060 0.3972 0.031 Uiso 1 1 calc R . . . .
C4 C 0.86686(12) 0.63829(17) 0.45904(8) 0.0315(3) Uani 1 1 d . . . . .
C5 C 0.92717(11) 0.63886(19) 0.52799(9) 0.0349(4) Uani 1 1 d . . . . .
H5 H 0.9962 0.6589 0.5385 0.042 Uiso 1 1 calc R . . . .
C6 C 0.88846(10) 0.61066(16) 0.58175(7) 0.0264(3) Uani 1 1 d . . . . .
H6 H 0.9301 0.6124 0.6288 0.032 Uiso 1 1 calc R . . . .
C7 C 0.90971(14) 0.6719(2) 0.40132(10) 0.0508(5) Uani 1 1 d . . . . .
H7A H 0.8901 0.5976 0.3656 0.076 Uiso 1 1 calc GR . . . .
H7B H 0.9826 0.6757 0.4202 0.076 Uiso 1 1 calc GR . . . .
H7C H 0.8843 0.7643 0.3807 0.076 Uiso 1 1 calc GR . . . .
C8 C 0.80229(9) 0.26331(13) 0.64568(6) 0.0164(2) Uani 1 1 d . . . . .
C9 C 0.89766(9) 0.29417(15) 0.68972(6) 0.0218(3) Uani 1 1 d . . . . .
H9 H 0.9121 0.3864 0.7098 0.026 Uiso 1 1 calc R . . . .
C10 C 0.97170(10) 0.19082(17) 0.70448(7) 0.0271(3) Uani 1 1 d . . . . .
H10 H 1.0369 0.2125 0.7340 0.033 Uiso 1 1 calc R . . . .
C11 C 0.95011(11) 0.05630(17) 0.67604(7) 0.0295(3) Uani 1 1 d . . . . .
H11 H 1.0004 -0.0150 0.6864 0.035 Uiso 1 1 calc R . . . .
C12 C 0.85508(11) 0.02524(15) 0.63241(7) 0.0256(3) Uani 1 1 d . . . . .
H12 H 0.8411 -0.0681 0.6137 0.031 Uiso 1 1 calc R . . . .
C13 C 0.77943(9) 0.12747(14) 0.61520(6) 0.0181(3) Uani 1 1 d . . . . .
C14 C 0.67552(9) 0.09303(13) 0.56360(6) 0.0176(2) Uani 1 1 d . . . . .
C15 C 0.59904(9) 0.12421(13) 0.59765(6) 0.0185(3) Uani 1 1 d . . . . .
C16 C 0.53964(9) 0.15715(13) 0.62627(6) 0.0188(3) Uani 1 1 d . . . . .
C17 C 0.47215(9) 0.19721(13) 0.66346(6) 0.0174(2) Uani 1 1 d . . . . .
C18 C 0.48926(10) 0.32130(14) 0.70388(7) 0.0209(3) Uani 1 1 d . . . . .
H18 H 0.5436 0.3818 0.7049 0.025 Uiso 1 1 calc R . . . .
C19 C 0.42680(10) 0.35577(14) 0.74241(7) 0.0235(3) Uani 1 1 d . . . . .
H19 H 0.4385 0.4401 0.7697 0.028 Uiso 1 1 calc R . . . .
C20 C 0.34731(10) 0.26790(15) 0.74133(7) 0.0234(3) Uani 1 1 d . . . . .
H20 H 0.3050 0.2919 0.7680 0.028 Uiso 1 1 calc R . . . .
C21 C 0.32970(10) 0.14475(15) 0.70121(7) 0.0234(3) Uani 1 1 d . . . . .
H21 H 0.2753 0.0846 0.7005 0.028 Uiso 1 1 calc R . . . .
C22 C 0.39130(10) 0.10942(14) 0.66223(7) 0.0205(3) Uani 1 1 d . . . . .
H22 H 0.3787 0.0255 0.6346 0.025 Uiso 1 1 calc R . . . .
C23 C 0.66458(11) -0.06588(14) 0.54205(8) 0.0256(3) Uani 1 1 d . . . . .
H23A H 0.6746 -0.1255 0.5834 0.038 Uiso 1 1 calc GR . . . .
H23B H 0.7145 -0.0902 0.5195 0.038 Uiso 1 1 calc GR . . . .
H23C H 0.5977 -0.0826 0.5096 0.038 Uiso 1 1 calc GR . . . .
C24 C 0.65565(9) 0.18216(12) 0.49762(6) 0.0160(2) Uani 1 1 d . . . . .
C25 C 0.71668(9) 0.18849(13) 0.45248(6) 0.0177(2) Uani 1 1 d . . . . .
C26 C 0.80934(10) 0.13001(15) 0.45445(7) 0.0248(3) Uani 1 1 d . . . . .
H26 H 0.8473 0.0758 0.4934 0.030 Uiso 1 1 calc R . . . .
C27 C 0.84403(12) 0.15299(18) 0.39866(8) 0.0328(3) Uani 1 1 d . . . . .
H27 H 0.9060 0.1127 0.3993 0.039 Uiso 1 1 calc R . . . .
C28 C 0.78975(12) 0.23455(18) 0.34112(8) 0.0335(3) Uani 1 1 d . . . . .
H28 H 0.8160 0.2492 0.3038 0.040 Uiso 1 1 calc R . . . .
C29 C 0.69912(11) 0.29373(15) 0.33782(7) 0.0271(3) Uani 1 1 d . . . . .
H29 H 0.6624 0.3491 0.2990 0.033 Uiso 1 1 calc R . . . .
C30 C 0.66329(10) 0.26928(13) 0.39368(6) 0.0199(3) Uani 1 1 d . . . . .
C31 C 0.57105(9) 0.25750(13) 0.46541(6) 0.0187(2) Uani 1 1 d . . . . .
H31 H 0.5170 0.2707 0.4833 0.022 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 1.4321(9) . ?
S1 O2 1.4347(9) . ?
S1 N1 1.6313(11) . ?
S1 C1 1.7557(12) . ?
N1 H1 0.846(17) . ?
N1 C8 1.4191(15) . ?
N2 H2 0.859(18) . ?
N2 C30 1.3743(18) . ?
N2 C31 1.3743(17) . ?
C1 C2 1.3927(18) . ?
C1 C6 1.3861(18) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3813(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(2) . ?
C4 C5 1.390(2) . ?
C4 C7 1.509(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.3935(18) . ?
C8 C13 1.4088(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3884(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.3965(18) . ?
C13 C14 1.5461(17) . ?
C14 C15 1.4815(17) . ?
C14 C23 1.5475(17) . ?
C14 C24 1.5260(17) . ?
C15 C16 1.2000(19) . ?
C16 C17 1.4377(17) . ?
C17 C18 1.4000(18) . ?
C17 C22 1.4021(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.3867(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3876(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.3858(19) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.4409(17) . ?
C24 C31 1.3656(17) . ?
C25 C26 1.4082(18) . ?
C25 C30 1.4140(18) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.404(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.378(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.3953(19) . ?
C31 H31 0.9500 . ?

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 119.67(5) . . ?
O1 S1 N1 109.40(6) . . ?
O1 S1 C1 107.57(6) . . ?
O2 S1 N1 103.31(5) . . ?
O2 S1 C1 109.20(6) . . ?
N1 S1 C1 107.05(6) . . ?
S1 N1 H1 110.8(11) . . ?
C8 N1 S1 127.78(9) . . ?
C8 N1 H1 116.8(11) . . ?
C30 N2 H2 126.8(11) . . ?
C31 N2 H2 123.7(11) . . ?
C31 N2 C30 108.98(11) . . ?
C2 C1 S1 118.82(10) . . ?
C6 C1 S1 119.97(10) . . ?
C6 C1 C2 121.19(12) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 C1 119.05(12) . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.01(13) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C7 120.57(15) . . ?
C5 C4 C3 118.80(13) . . ?
C5 C4 C7 120.62(15) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.29(14) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.65(13) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N1 120.06(12) . . ?
C9 C8 C13 120.76(12) . . ?
C13 C8 N1 119.12(11) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.32(13) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.69(13) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.05(13) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.80(14) . . ?
C13 C12 H12 119.1 . . ?
C8 C13 C14 121.61(11) . . ?
C12 C13 C8 117.35(12) . . ?
C12 C13 C14 121.03(12) . . ?
C13 C14 C23 112.45(10) . . ?
C15 C14 C13 108.69(10) . . ?
C15 C14 C23 107.37(10) . . ?
C15 C14 C24 109.78(10) . . ?
C24 C14 C13 110.65(10) . . ?
C24 C14 C23 107.83(10) . . ?
C16 C15 C14 176.17(13) . . ?
C15 C16 C17 177.40(13) . . ?
C18 C17 C16 120.16(11) . . ?
C18 C17 C22 119.30(12) . . ?
C22 C17 C16 120.48(11) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.95(12) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.46(12) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.94(12) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.18(12) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.17(12) . . ?
C21 C22 H22 119.9 . . ?
C14 C23 H23A 109.5 . . ?
C14 C23 H23B 109.5 . . ?
C14 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C14 126.55(11) . . ?
C31 C24 C14 126.54(11) . . ?
C31 C24 C25 106.47(11) . . ?
C26 C25 C24 134.55(12) . . ?
C26 C25 C30 118.59(12) . . ?
C30 C25 C24 106.81(11) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 C25 118.71(13) . . ?
C27 C26 H26 120.6 . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.49(14) . . ?
C28 C27 H27 119.3 . . ?
C27 C28 H28 119.4 . . ?
C29 C28 C27 121.15(13) . . ?
C29 C28 H28 119.4 . . ?
C28 C29 H29 121.2 . . ?
C28 C29 C30 117.51(13) . . ?
C30 C29 H29 121.2 . . ?
N2 C30 C25 107.56(11) . . ?
N2 C30 C29 129.89(13) . . ?
C29 C30 C25 122.53(13) . . ?
N2 C31 H31 124.9 . . ?
C24 C31 N2 110.16(11) . . ?
C24 C31 H31 124.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O2 0.859(18) 2.453(17) 3.0426(15) 126.4(14) 3_666

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 C8 C9 32.08(16) . . . . ?
S1 N1 C8 C13 -150.78(10) . . . . ?
S1 C1 C2 C3 -179.18(10) . . . . ?
S1 C1 C6 C5 178.66(12) . . . . ?
O1 S1 N1 C8 -56.14(11) . . . . ?
O1 S1 C1 C2 -164.22(10) . . . . ?
O1 S1 C1 C6 16.80(13) . . . . ?
O2 S1 N1 C8 175.35(10) . . . . ?
O2 S1 C1 C2 -32.91(12) . . . . ?
O2 S1 C1 C6 148.10(11) . . . . ?
N1 S1 C1 C2 78.29(11) . . . . ?
N1 S1 C1 C6 -100.69(11) . . . . ?
N1 C8 C9 C10 176.81(11) . . . . ?
N1 C8 C13 C12 -175.46(11) . . . . ?
N1 C8 C13 C14 5.70(17) . . . . ?
C1 S1 N1 C8 60.14(11) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C2 C3 C4 C7 -179.34(15) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C6 C1 C2 C3 -0.21(19) . . . . ?
C7 C4 C5 C6 178.82(16) . . . . ?
C8 C9 C10 C11 -0.89(19) . . . . ?
C8 C13 C14 C15 -56.09(14) . . . . ?
C8 C13 C14 C23 -174.83(11) . . . . ?
C8 C13 C14 C24 64.52(14) . . . . ?
C9 C8 C13 C12 1.65(17) . . . . ?
C9 C8 C13 C14 -177.19(11) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C11 C12 C13 C8 -1.95(19) . . . . ?
C11 C12 C13 C14 176.91(12) . . . . ?
C12 C13 C14 C15 125.11(12) . . . . ?
C12 C13 C14 C23 6.37(16) . . . . ?
C12 C13 C14 C24 -114.28(13) . . . . ?
C13 C8 C9 C10 -0.28(18) . . . . ?
C13 C14 C24 C25 56.04(15) . . . . ?
C13 C14 C24 C31 -132.53(13) . . . . ?
C14 C24 C25 C26 -4.7(2) . . . . ?
C14 C24 C25 C30 172.53(11) . . . . ?
C14 C24 C31 N2 -173.26(11) . . . . ?
C15 C14 C24 C25 176.00(11) . . . . ?
C15 C14 C24 C31 -12.57(17) . . . . ?
C16 C17 C18 C19 -176.78(12) . . . . ?
C16 C17 C22 C21 176.49(12) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C17 C22 C21 -0.61(19) . . . . ?
C18 C19 C20 C21 -0.3(2) . . . . ?
C19 C20 C21 C22 0.0(2) . . . . ?
C20 C21 C22 C17 0.5(2) . . . . ?
C22 C17 C18 C19 0.32(19) . . . . ?
C23 C14 C24 C25 -67.32(15) . . . . ?
C23 C14 C24 C31 104.11(14) . . . . ?
C24 C25 C26 C27 176.52(14) . . . . ?
C24 C25 C30 N2 0.91(13) . . . . ?
C24 C25 C30 C29 -178.07(12) . . . . ?
C25 C24 C31 N2 -0.43(14) . . . . ?
C25 C26 C27 C28 0.9(2) . . . . ?
C26 C25 C30 N2 178.67(11) . . . . ?
C26 C25 C30 C29 -0.31(19) . . . . ?
C26 C27 C28 C29 -0.6(2) . . . . ?
C27 C28 C29 C30 -0.2(2) . . . . ?
C28 C29 C30 N2 -178.11(13) . . . . ?
C28 C29 C30 C25 0.6(2) . . . . ?
C30 N2 C31 C24 1.03(14) . . . . ?
C30 C25 C26 C27 -0.47(19) . . . . ?
C31 N2 C30 C25 -1.19(14) . . . . ?
C31 N2 C30 C29 177.69(13) . . . . ?
C31 C24 C25 C26 -177.54(14) . . . . ?
C31 C24 C25 C30 -0.30(13) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 1016688'
