# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_cd17055
_audit_block_doi                 10.5517/ccdc.csd.cc1nf6q0
_database_code_depnum_ccdc_archive 'CCDC 1532042'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jacs.7b02027 2017
_audit_update_record             
;
2017-02-10 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H29 N O3 S'
_chemical_formula_weight         483.60

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   9.8296(13)
_cell_length_b                   13.4413(17)
_cell_length_c                   22.608(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.433(3)
_cell_angle_gamma                90
_cell_volume                     2978.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1706
_cell_measurement_theta_min      5.144
_cell_measurement_theta_max      38.958

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6428
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16120
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.764
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             5236
_reflns_number_gt                3268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0824P)²+0.0700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5236
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1781
_refine_ls_wR_factor_gt          0.1582
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.020 0.000 0.000 334 64 ' '
2 0.003 0.500 0.500 334 64 ' '
_platon_squeeze_details          
;
;


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 0.66065(9) 0.63137(7) 0.04912(4) 0.0660(3) Uani 1 1 d . . . . .
N1 N 0.6125(2) 0.52815(19) 0.07980(10) 0.0577(7) Uani 1 1 d . . . . .
O1 O 0.37013(19) 0.46429(16) 0.13127(9) 0.0597(6) Uani 1 1 d . . . . .
H1 H 0.3679 0.4472 0.0964 0.090 Uiso 1 1 calc R U . . .
O2 O 0.5783(2) 0.70916(18) 0.07003(11) 0.0843(7) Uani 1 1 d . . . . .
O3 O 0.6608(3) 0.6116(2) -0.01281(9) 0.0950(9) Uani 1 1 d . . . . .
C1 C 0.5030(3) 0.4459(2) 0.15927(12) 0.0480(7) Uani 1 1 d . . . . .
C2 C 0.5971(3) 0.5306(2) 0.14292(12) 0.0534(8) Uani 1 1 d . . . . .
H2A H 0.5586 0.5940 0.1536 0.064 Uiso 1 1 calc R U . . .
H2B H 0.6855 0.5234 0.1646 0.064 Uiso 1 1 calc R U . . .
C3 C 0.6775(3) 0.4372(2) 0.06053(13) 0.0611(8) Uani 1 1 d . . . . .
H3A H 0.7756 0.4443 0.0675 0.073 Uiso 1 1 calc R U . . .
H3B H 0.6565 0.4293 0.0182 0.073 Uiso 1 1 calc R U . . .
C4 C 0.6340(3) 0.3454(2) 0.09139(13) 0.0526(7) Uani 1 1 d . . . . .
C5 C 0.5579(3) 0.3473(2) 0.13788(12) 0.0478(7) Uani 1 1 d . . . . .
C6 C 0.5124(3) 0.2552(2) 0.16656(12) 0.0500(7) Uani 1 1 d . . . . .
C7 C 0.3632(3) 0.2370(2) 0.16591(16) 0.0739(10) Uani 1 1 d . . . . .
H7A H 0.3474 0.1704 0.1791 0.111 Uiso 1 1 calc R U . . .
H7B H 0.3221 0.2455 0.1263 0.111 Uiso 1 1 calc R U . . .
H7C H 0.3237 0.2835 0.1919 0.111 Uiso 1 1 calc R U . . .
C8 C 0.6020(3) 0.1899(2) 0.19098(13) 0.0588(8) Uani 1 1 d . . . . .
H8 H 0.6940 0.2062 0.1911 0.071 Uiso 1 1 calc R U . . .
C9 C 0.5690(3) 0.0982(3) 0.21661(14) 0.0615(8) Uani 1 1 d . . . . .
C10 C 0.5454(3) 0.0191(3) 0.23873(15) 0.0632(9) Uani 1 1 d . . . . .
C11 C 0.5233(3) -0.0731(2) 0.26786(15) 0.0564(8) Uani 1 1 d . . . . .
C12 C 0.5298(3) -0.1638(3) 0.23894(17) 0.0754(10) Uani 1 1 d . . . . .
H12 H 0.5448 -0.1660 0.1988 0.090 Uiso 1 1 calc R U . . .
C13 C 0.5136(4) -0.2514(3) 0.2704(2) 0.0869(12) Uani 1 1 d . . . . .
H13 H 0.5199 -0.3122 0.2512 0.104 Uiso 1 1 calc R U . . .
C14 C 0.4889(4) -0.2496(3) 0.3285(2) 0.0817(11) Uani 1 1 d . . . . .
H14 H 0.4777 -0.3086 0.3490 0.098 Uiso 1 1 calc R U . . .
C15 C 0.4809(4) -0.1616(3) 0.35585(17) 0.0796(10) Uani 1 1 d . . . . .
H15 H 0.4639 -0.1604 0.3957 0.096 Uiso 1 1 calc R U . . .
C16 C 0.4969(3) -0.0741(3) 0.32697(16) 0.0695(9) Uani 1 1 d . . . . .
H16 H 0.4900 -0.0143 0.3472 0.083 Uiso 1 1 calc R U . . .
C17 C 0.6807(3) 0.2531(3) 0.06197(15) 0.0752(10) Uani 1 1 d . . . . .
H17A H 0.6471 0.1957 0.0815 0.113 Uiso 1 1 calc R U . . .
H17B H 0.7786 0.2514 0.0645 0.113 Uiso 1 1 calc R U . . .
H17C H 0.6464 0.2529 0.0210 0.113 Uiso 1 1 calc R U . . .
C18 C 0.4916(3) 0.4514(2) 0.22572(12) 0.0490(7) Uani 1 1 d . . . . .
C19 C 0.3692(3) 0.4706(2) 0.24970(15) 0.0638(9) Uani 1 1 d . . . . .
H19 H 0.2899 0.4772 0.2248 0.077 Uiso 1 1 calc R U . . .
C20 C 0.3633(5) 0.4802(3) 0.30956(18) 0.0816(11) Uani 1 1 d . . . . .
H20 H 0.2798 0.4918 0.3251 0.098 Uiso 1 1 calc R U . . .
C21 C 0.4780(6) 0.4728(3) 0.34652(18) 0.0885(12) Uani 1 1 d . . . . .
H21 H 0.4734 0.4808 0.3872 0.106 Uiso 1 1 calc R U . . .
C22 C 0.6005(4) 0.4537(3) 0.32413(15) 0.0773(10) Uani 1 1 d . . . . .
H22 H 0.6792 0.4482 0.3495 0.093 Uiso 1 1 calc R U . . .
C23 C 0.6072(3) 0.4426(2) 0.26384(13) 0.0603(8) Uani 1 1 d . . . . .
H23 H 0.6906 0.4290 0.2487 0.072 Uiso 1 1 calc R U . . .
C24 C 0.8303(3) 0.6535(2) 0.07538(12) 0.0539(8) Uani 1 1 d . . . . .
C25 C 0.8601(3) 0.7001(2) 0.12887(13) 0.0547(8) Uani 1 1 d . . . . .
H25 H 0.7900 0.7205 0.1515 0.066 Uiso 1 1 calc R U . . .
C26 C 0.9930(3) 0.7162(2) 0.14875(14) 0.0582(8) Uani 1 1 d . . . . .
H26 H 1.0117 0.7474 0.1852 0.070 Uiso 1 1 calc R U . . .
C27 C 1.0992(3) 0.6882(2) 0.11720(16) 0.0634(9) Uani 1 1 d . . . . .
C28 C 1.0689(4) 0.6400(3) 0.06402(17) 0.0790(11) Uani 1 1 d . . . . .
H28 H 1.1399 0.6190 0.0421 0.095 Uiso 1 1 calc R U . . .
C29 C 0.9363(4) 0.6222(3) 0.04252(14) 0.0705(10) Uani 1 1 d . . . . .
H29 H 0.9178 0.5897 0.0065 0.085 Uiso 1 1 calc R U . . .
C30 C 1.2432(3) 0.7097(3) 0.1399(2) 0.1004(13) Uani 1 1 d . . . . .
H30A H 1.2621 0.7791 0.1347 0.151 Uiso 1 1 calc R U . . .
H30B H 1.3044 0.6707 0.1183 0.151 Uiso 1 1 calc R U . . .
H30C H 1.2554 0.6931 0.1813 0.151 Uiso 1 1 calc R U . . .


_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 O3 1.425(2) . ?
S1 O2 1.425(3) . ?
S1 N1 1.637(3) . ?
S1 C24 1.752(3) . ?
N1 C2 1.447(4) . ?
N1 C3 1.461(4) . ?
O1 C1 1.428(3) . ?
O1 H1 0.8200 . ?
C1 C18 1.517(4) . ?
C1 C5 1.524(4) . ?
C1 C2 1.530(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.496(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.337(4) . ?
C4 C17 1.497(4) . ?
C5 C6 1.482(4) . ?
C6 C8 1.332(4) . ?
C6 C7 1.486(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.411(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.205(4) . ?
C10 C11 1.429(5) . ?
C11 C16 1.381(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.391(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.354(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.340(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.360(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.377(4) . ?
C18 C19 1.382(4) . ?
C19 C20 1.365(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.354(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.373(4) . ?
C24 C29 1.390(4) . ?
C25 C26 1.366(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.362(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.378(5) . ?
C27 C30 1.496(4) . ?
C28 C29 1.377(5) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
O3 S1 O2 120.41(16) . . ?
O3 S1 N1 106.28(14) . . ?
O2 S1 N1 106.91(14) . . ?
O3 S1 C24 106.95(15) . . ?
O2 S1 C24 108.26(15) . . ?
N1 S1 C24 107.41(13) . . ?
C2 N1 C3 113.3(2) . . ?
C2 N1 S1 117.0(2) . . ?
C3 N1 S1 115.8(2) . . ?
C1 O1 H1 109.5 . . ?
O1 C1 C18 107.2(2) . . ?
O1 C1 C5 110.1(2) . . ?
C18 C1 C5 114.3(2) . . ?
O1 C1 C2 108.2(2) . . ?
C18 C1 C2 107.2(2) . . ?
C5 C1 C2 109.6(2) . . ?
N1 C2 C1 109.4(2) . . ?
N1 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 C4 113.8(2) . . ?
N1 C3 H3A 108.8 . . ?
C4 C3 H3A 108.8 . . ?
N1 C3 H3B 108.8 . . ?
C4 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 123.3(3) . . ?
C5 C4 C17 125.1(3) . . ?
C3 C4 C17 111.6(3) . . ?
C4 C5 C6 122.3(3) . . ?
C4 C5 C1 120.0(3) . . ?
C6 C5 C1 117.5(2) . . ?
C8 C6 C5 121.3(3) . . ?
C8 C6 C7 121.1(3) . . ?
C5 C6 C7 117.6(2) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 C9 125.4(3) . . ?
C6 C8 H8 117.3 . . ?
C9 C8 H8 117.3 . . ?
C10 C9 C8 177.8(3) . . ?
C9 C10 C11 176.5(3) . . ?
C16 C11 C12 117.8(3) . . ?
C16 C11 C10 120.1(3) . . ?
C12 C11 C10 122.1(3) . . ?
C11 C12 C13 119.5(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 121.1(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 121.9(4) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C11 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 118.2(3) . . ?
C23 C18 C1 119.7(3) . . ?
C19 C18 C1 122.0(3) . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 120.5(4) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 119.9(4) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 120.6(3) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C29 119.4(3) . . ?
C25 C24 S1 120.5(2) . . ?
C29 C24 S1 120.0(2) . . ?
C26 C25 C24 119.7(3) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C27 C26 C25 122.4(3) . . ?
C27 C26 H26 118.8 . . ?
C25 C26 H26 118.8 . . ?
C26 C27 C28 117.7(3) . . ?
C26 C27 C30 120.7(3) . . ?
C28 C27 C30 121.7(3) . . ?
C29 C28 C27 121.6(3) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C28 C29 C24 119.1(3) . . ?
C28 C29 H29 120.4 . . ?
C24 C29 H29 120.4 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
O3 S1 N1 C2 -176.8(2) . . . . ?
O2 S1 N1 C2 -47.0(2) . . . . ?
C24 S1 N1 C2 69.0(2) . . . . ?
O3 S1 N1 C3 45.6(2) . . . . ?
O2 S1 N1 C3 175.4(2) . . . . ?
C24 S1 N1 C3 -68.6(2) . . . . ?
C3 N1 C2 C1 -62.8(3) . . . . ?
S1 N1 C2 C1 158.51(19) . . . . ?
O1 C1 C2 N1 -65.2(3) . . . . ?
C18 C1 C2 N1 179.5(2) . . . . ?
C5 C1 C2 N1 54.9(3) . . . . ?
C2 N1 C3 C4 38.7(3) . . . . ?
S1 N1 C3 C4 177.90(18) . . . . ?
N1 C3 C4 C5 -8.8(4) . . . . ?
N1 C3 C4 C17 168.5(2) . . . . ?
C3 C4 C5 C6 178.0(3) . . . . ?
C17 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C5 C1 4.2(4) . . . . ?
C17 C4 C5 C1 -172.8(3) . . . . ?
O1 C1 C5 C4 92.2(3) . . . . ?
C18 C1 C5 C4 -147.1(3) . . . . ?
C2 C1 C5 C4 -26.8(3) . . . . ?
O1 C1 C5 C6 -82.0(3) . . . . ?
C18 C1 C5 C6 38.8(3) . . . . ?
C2 C1 C5 C6 159.1(2) . . . . ?
C4 C5 C6 C8 60.5(4) . . . . ?
C1 C5 C6 C8 -125.5(3) . . . . ?
C4 C5 C6 C7 -118.2(3) . . . . ?
C1 C5 C6 C7 55.8(3) . . . . ?
C5 C6 C8 C9 -176.7(3) . . . . ?
C7 C6 C8 C9 1.9(5) . . . . ?
C16 C11 C12 C13 -1.8(5) . . . . ?
C10 C11 C12 C13 177.0(3) . . . . ?
C11 C12 C13 C14 1.4(5) . . . . ?
C12 C13 C14 C15 -0.4(6) . . . . ?
C13 C14 C15 C16 0.0(6) . . . . ?
C14 C15 C16 C11 -0.5(5) . . . . ?
C12 C11 C16 C15 1.4(5) . . . . ?
C10 C11 C16 C15 -177.4(3) . . . . ?
O1 C1 C18 C23 -176.0(2) . . . . ?
C5 C1 C18 C23 61.7(3) . . . . ?
C2 C1 C18 C23 -60.0(3) . . . . ?
O1 C1 C18 C19 0.4(4) . . . . ?
C5 C1 C18 C19 -122.0(3) . . . . ?
C2 C1 C18 C19 116.4(3) . . . . ?
C23 C18 C19 C20 -0.3(4) . . . . ?
C1 C18 C19 C20 -176.7(3) . . . . ?
C18 C19 C20 C21 1.3(5) . . . . ?
C19 C20 C21 C22 -1.4(6) . . . . ?
C20 C21 C22 C23 0.5(5) . . . . ?
C19 C18 C23 C22 -0.6(4) . . . . ?
C1 C18 C23 C22 175.8(3) . . . . ?
C21 C22 C23 C18 0.6(5) . . . . ?
O3 S1 C24 C25 162.5(2) . . . . ?
O2 S1 C24 C25 31.4(3) . . . . ?
N1 S1 C24 C25 -83.7(3) . . . . ?
O3 S1 C24 C29 -18.6(3) . . . . ?
O2 S1 C24 C29 -149.8(3) . . . . ?
N1 S1 C24 C29 95.1(3) . . . . ?
C29 C24 C25 C26 0.8(4) . . . . ?
S1 C24 C25 C26 179.6(2) . . . . ?
C24 C25 C26 C27 0.4(5) . . . . ?
C25 C26 C27 C28 -1.5(5) . . . . ?
C25 C26 C27 C30 178.4(3) . . . . ?
C26 C27 C28 C29 1.3(5) . . . . ?
C30 C27 C28 C29 -178.5(3) . . . . ?
C27 C28 C29 C24 -0.2(5) . . . . ?
C25 C24 C29 C28 -0.9(5) . . . . ?
S1 C24 C29 C28 -179.8(3) . . . . ?

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
O1 H1 O3 0.82 2.05 2.860(3) 170.9 3_665
O1 H1 O3 0.82 2.05 2.860(3) 170.9 3_665

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_mo_d8v18177_0m
_database_code_depnum_ccdc_archive 'CCDC 1823053'
loop_
_audit_author_name
_audit_author_address
'Min Shi' 'Shanghai Institute of Organic Chemistry'
_audit_update_record             
;
2018-02-09 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H27 N O2 S'
_chemical_formula_weight         345.48

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_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                   5.8832(2)
_cell_length_b                   8.7875(2)
_cell_length_c                   37.5443(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1940.99(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5004
_cell_measurement_theta_min      6.351
_cell_measurement_theta_max      53.224

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.178
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6188
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10672
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         3.176
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3773
_reflns_number_gt                3176
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0695P)²+0.0867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.020(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1088 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.02(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3773
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.009

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 0.61890(14) 0.27703(11) 0.66942(2) 0.0687(3) Uani 1 1 d . . . . .
N1 N 0.4810(4) 0.3642(3) 0.63795(6) 0.0595(6) Uani 1 1 d . . . . .
O1 O 0.6523(5) 0.1239(3) 0.65754(6) 0.0900(8) Uani 1 1 d . . . . .
O2 O 0.8110(4) 0.3701(4) 0.67794(7) 0.0936(9) Uani 1 1 d . . . . .
C1 C 0.4220(6) 0.5252(3) 0.64315(8) 0.0616(8) Uani 1 1 d . . . . .
H1A H 0.5255 0.5718 0.6600 0.074 Uiso 1 1 calc R U . . .
H1B H 0.2685 0.5341 0.6523 0.074 Uiso 1 1 calc R U . . .
C2 C 0.4402(5) 0.6033(3) 0.60721(8) 0.0568(7) Uani 1 1 d . . . . .
C3 C 0.3213(7) 0.7578(4) 0.60522(10) 0.0750(9) Uani 1 1 d . . . . .
H3A H 0.1860 0.7591 0.6200 0.090 Uiso 1 1 calc R U . . .
H3B H 0.4222 0.8388 0.6129 0.090 Uiso 1 1 calc R U . . .
C4 C 0.2609(7) 0.7748(4) 0.56659(10) 0.0826(10) Uani 1 1 d . . . . .
H4A H 0.1157 0.8261 0.5642 0.099 Uiso 1 1 calc R U . . .
H4B H 0.3755 0.8349 0.5544 0.099 Uiso 1 1 calc R U . . .
C5 C 0.2487(6) 0.6234(4) 0.55109(9) 0.0677(9) Uani 1 1 d . . . . .
C6 C 0.3104(5) 0.5132(3) 0.57938(7) 0.0504(6) Uani 1 1 d . . . . .
C7 C 0.2484(5) 0.3684(3) 0.58366(7) 0.0482(6) Uani 1 1 d . . . . .
C8 C 0.3122(5) 0.2821(3) 0.61715(7) 0.0550(7) Uani 1 1 d . . . . .
H8A H 0.1773 0.2662 0.6315 0.066 Uiso 1 1 calc R U . . .
H8B H 0.3722 0.1831 0.6107 0.066 Uiso 1 1 calc R U . . .
C9 C 0.6923(6) 0.6186(5) 0.59638(11) 0.0805(10) Uani 1 1 d . . . . .
H9A H 0.7656 0.5214 0.5984 0.121 Uiso 1 1 calc R U . . .
H9B H 0.7661 0.6903 0.6118 0.121 Uiso 1 1 calc R U . . .
H9C H 0.7019 0.6536 0.5722 0.121 Uiso 1 1 calc R U . . .
C10 C 0.1960(11) 0.5969(6) 0.51595(11) 0.1011(16) Uani 1 1 d . . . . .
C11 C 0.1112(5) 0.2760(3) 0.55693(7) 0.0558(7) Uani 1 1 d . . . . .
H11 H 0.0318 0.3485 0.5415 0.067 Uiso 1 1 calc R U . . .
C12 C 0.2703(7) 0.1841(4) 0.53337(9) 0.0704(9) Uani 1 1 d . . . . .
H12A H 0.3691 0.2518 0.5206 0.106 Uiso 1 1 calc R U . . .
H12B H 0.1827 0.1254 0.5167 0.106 Uiso 1 1 calc R U . . .
H12C H 0.3596 0.1169 0.5479 0.106 Uiso 1 1 calc R U . . .
C13 C -0.0686(6) 0.1743(4) 0.57377(9) 0.0763(10) Uani 1 1 d . . . . .
H13A H 0.0036 0.1011 0.5890 0.114 Uiso 1 1 calc R U . . .
H13B H -0.1514 0.1224 0.5554 0.114 Uiso 1 1 calc R U . . .
H13C H -0.1714 0.2354 0.5875 0.114 Uiso 1 1 calc R U . . .
C14 C 0.4433(5) 0.2724(4) 0.70750(7) 0.0575(7) Uani 1 1 d . . . . .
C15 C 0.2561(6) 0.1766(4) 0.70822(8) 0.0708(9) Uani 1 1 d . . . . .
H15 H 0.2227 0.1147 0.6888 0.085 Uiso 1 1 calc R U . . .
C16 C 0.1198(6) 0.1747(4) 0.73826(9) 0.0765(10) Uani 1 1 d . . . . .
H16 H -0.0077 0.1122 0.7387 0.092 Uiso 1 1 calc R U . . .
C17 C 0.1694(6) 0.2638(4) 0.76763(8) 0.0722(9) Uani 1 1 d . . . . .
C18 C 0.3548(8) 0.3572(5) 0.76606(9) 0.0805(10) Uani 1 1 d . . . . .
H18 H 0.3899 0.4180 0.7856 0.097 Uiso 1 1 calc R U . . .
C19 C 0.4911(7) 0.3635(5) 0.73621(8) 0.0753(9) Uani 1 1 d . . . . .
H19 H 0.6150 0.4292 0.7355 0.090 Uiso 1 1 calc R U . . .
C20 C 0.0218(8) 0.2576(6) 0.80053(11) 0.1081(15) Uani 1 1 d . . . . .
H20A H -0.1345 0.2472 0.7936 0.162 Uiso 1 1 calc R U . . .
H20B H 0.0407 0.3495 0.8140 0.162 Uiso 1 1 calc R U . . .
H20C H 0.0654 0.1720 0.8149 0.162 Uiso 1 1 calc R U . . .
H10A H 0.178(6) 0.678(4) 0.5028(10) 0.081(12) Uiso 1 1 d . . . . .
H10B H 0.233(11) 0.504(6) 0.5056(13) 0.15(2) 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 1.431(3) . ?
S1 O2 1.431(3) . ?
S1 N1 1.625(2) . ?
S1 C14 1.764(3) . ?
N1 C8 1.455(4) . ?
N1 C1 1.469(4) . ?
C1 C2 1.518(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C6 1.517(4) . ?
C2 C3 1.530(4) . ?
C2 C9 1.544(5) . ?
C3 C4 1.501(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.454(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.375(5) . ?
C5 C6 1.483(4) . ?
C6 C7 1.333(4) . ?
C7 C8 1.516(4) . ?
C7 C11 1.522(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.87(4) . ?
C10 H10B 0.93(5) . ?
C11 C12 1.520(4) . ?
C11 C13 1.522(5) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.372(5) . ?
C14 C15 1.386(5) . ?
C15 C16 1.384(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(6) . ?
C17 C20 1.511(5) . ?
C18 C19 1.380(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 119.90(19) . . ?
O1 S1 N1 106.57(14) . . ?
O2 S1 N1 106.68(16) . . ?
O1 S1 C14 108.13(16) . . ?
O2 S1 C14 107.13(15) . . ?
N1 S1 C14 107.93(13) . . ?
C8 N1 C1 112.8(2) . . ?
C8 N1 S1 119.8(2) . . ?
C1 N1 S1 118.4(2) . . ?
N1 C1 C2 107.5(2) . . ?
N1 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
N1 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C6 C2 C1 109.9(2) . . ?
C6 C2 C3 101.5(2) . . ?
C1 C2 C3 114.4(3) . . ?
C6 C2 C9 110.4(3) . . ?
C1 C2 C9 110.0(3) . . ?
C3 C2 C9 110.4(3) . . ?
C4 C3 C2 104.1(3) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 109.0 . . ?
C5 C4 C3 107.9(3) . . ?
C5 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C10 C5 C4 123.3(4) . . ?
C10 C5 C6 129.2(4) . . ?
C4 C5 C6 107.4(3) . . ?
C7 C6 C5 130.0(3) . . ?
C7 C6 C2 123.6(2) . . ?
C5 C6 C2 106.0(3) . . ?
C6 C7 C8 120.6(3) . . ?
C6 C7 C11 125.1(2) . . ?
C8 C7 C11 114.3(2) . . ?
N1 C8 C7 111.5(2) . . ?
N1 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 116(2) . . ?
C5 C10 H10B 120(3) . . ?
H10A C10 H10B 121(4) . . ?
C12 C11 C13 111.0(3) . . ?
C12 C11 C7 109.9(3) . . ?
C13 C11 C7 114.0(2) . . ?
C12 C11 H11 107.2 . . ?
C13 C11 H11 107.2 . . ?
C7 C11 H11 107.2 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 120.1(3) . . ?
C19 C14 S1 120.2(3) . . ?
C15 C14 S1 119.7(2) . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 118.3(3) . . ?
C18 C17 C20 121.1(4) . . ?
C16 C17 C20 120.6(4) . . ?
C17 C18 C19 121.5(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C18 119.7(3) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C8 35.0(3) . . . . ?
O2 S1 N1 C8 164.2(2) . . . . ?
C14 S1 N1 C8 -81.0(2) . . . . ?
O1 S1 N1 C1 179.7(2) . . . . ?
O2 S1 N1 C1 -51.1(3) . . . . ?
C14 S1 N1 C1 63.8(3) . . . . ?
C8 N1 C1 C2 -68.6(3) . . . . ?
S1 N1 C1 C2 144.3(2) . . . . ?
N1 C1 C2 C6 49.9(3) . . . . ?
N1 C1 C2 C3 163.3(3) . . . . ?
N1 C1 C2 C9 -71.8(3) . . . . ?
C6 C2 C3 C4 -34.7(3) . . . . ?
C1 C2 C3 C4 -153.0(3) . . . . ?
C9 C2 C3 C4 82.4(3) . . . . ?
C2 C3 C4 C5 23.7(4) . . . . ?
C3 C4 C5 C10 179.7(4) . . . . ?
C3 C4 C5 C6 -2.3(4) . . . . ?
C10 C5 C6 C7 -30.1(6) . . . . ?
C4 C5 C6 C7 152.2(3) . . . . ?
C10 C5 C6 C2 157.5(5) . . . . ?
C4 C5 C6 C2 -20.3(4) . . . . ?
C1 C2 C6 C7 -17.7(4) . . . . ?
C3 C2 C6 C7 -139.1(3) . . . . ?
C9 C2 C6 C7 103.8(3) . . . . ?
C1 C2 C6 C5 155.3(2) . . . . ?
C3 C2 C6 C5 33.9(3) . . . . ?
C9 C2 C6 C5 -83.2(3) . . . . ?
C5 C6 C7 C8 -173.1(3) . . . . ?
C2 C6 C7 C8 -1.8(4) . . . . ?
C5 C6 C7 C11 6.6(5) . . . . ?
C2 C6 C7 C11 177.8(2) . . . . ?
C1 N1 C8 C7 48.2(3) . . . . ?
S1 N1 C8 C7 -165.20(19) . . . . ?
C6 C7 C8 N1 -12.4(4) . . . . ?
C11 C7 C8 N1 168.0(2) . . . . ?
C6 C7 C11 C12 95.4(3) . . . . ?
C8 C7 C11 C12 -84.9(3) . . . . ?
C6 C7 C11 C13 -139.2(3) . . . . ?
C8 C7 C11 C13 40.4(3) . . . . ?
O1 S1 C14 C19 137.9(3) . . . . ?
O2 S1 C14 C19 7.3(3) . . . . ?
N1 S1 C14 C19 -107.2(3) . . . . ?
O1 S1 C14 C15 -42.4(3) . . . . ?
O2 S1 C14 C15 -173.0(3) . . . . ?
N1 S1 C14 C15 72.5(3) . . . . ?
C19 C14 C15 C16 -0.1(5) . . . . ?
S1 C14 C15 C16 -179.8(3) . . . . ?
C14 C15 C16 C17 -1.3(5) . . . . ?
C15 C16 C17 C18 1.4(5) . . . . ?
C15 C16 C17 C20 -178.6(3) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C20 C17 C18 C19 179.8(4) . . . . ?
C15 C14 C19 C18 1.3(5) . . . . ?
S1 C14 C19 C18 -179.0(3) . . . . ?
C17 C18 C19 C14 -1.1(6) . . . . ?

_refine_diff_density_max         0.134
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cd17267
_database_code_depnum_ccdc_archive 'CCDC 1549540'
_audit_update_record             
;
2017-05-12 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H29 N O2 S'
_chemical_formula_weight         371.52

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_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                   8.8700(16)
_cell_length_b                   10.6671(18)
_cell_length_c                   21.508(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2035.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1317
_cell_measurement_theta_min      4.968
_cell_measurement_theta_max      38.969

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.174
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6245
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11111
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_av_R_equivalents  0.0649
_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       22
_diffrn_reflns_theta_min         1.894
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3602
_reflns_number_gt                2508
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.977

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 833 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.03(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3602
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1128
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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_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 0.41258(13) 0.67685(9) 0.81108(6) 0.0543(3) Uani 1 1 d . . . . .
N1 N 0.4312(4) 0.7358(3) 0.88024(15) 0.0536(10) Uani 1 1 d . . . . .
O1 O 0.3568(3) 0.5521(2) 0.81826(16) 0.0667(9) Uani 1 1 d . . . . .
O2 O 0.3270(4) 0.7663(3) 0.77623(14) 0.0664(9) Uani 1 1 d . . . . .
C1 C 0.4518(5) 0.7031(4) 0.9899(2) 0.0539(12) Uani 1 1 d . . . . .
H1 H 0.3436 0.6853 0.9928 0.065 Uiso 1 1 calc R U . . .
C2 C 0.5305(6) 0.6459(4) 1.0474(2) 0.0705(15) Uani 1 1 d . . . . .
H2A H 0.4731 0.5763 1.0642 0.085 Uiso 1 1 calc R U . . .
H2B H 0.6316 0.6177 1.0375 0.085 Uiso 1 1 calc R U . . .
C3 C 0.5335(6) 0.7531(5) 1.0913(2) 0.0700(14) Uani 1 1 d . . . . .
H3 H 0.5537 0.7443 1.1335 0.084 Uiso 1 1 calc R U . . .
C4 C 0.5048(5) 0.8625(4) 1.0647(2) 0.0540(11) Uani 1 1 d . . . . .
C5 C 0.4746(4) 0.8426(4) 0.99802(19) 0.0462(10) Uani 1 1 d . . . . .
C6 C 0.4771(5) 0.9195(4) 0.94897(19) 0.0451(10) Uani 1 1 d . . . . .
C7 C 0.4600(6) 0.8701(3) 0.8838(2) 0.0612(13) Uani 1 1 d . . . . .
H7A H 0.3775 0.9141 0.8638 0.073 Uiso 1 1 calc R U . . .
H7B H 0.5512 0.8888 0.8607 0.073 Uiso 1 1 calc R U . . .
C8 C 0.5074(5) 0.6586(4) 0.9274(2) 0.0583(12) Uani 1 1 d . . . . .
H8A H 0.6159 0.6686 0.9244 0.070 Uiso 1 1 calc R U . . .
H8B H 0.4830 0.5707 0.9215 0.070 Uiso 1 1 calc R U . . .
C9 C 0.5124(6) 0.9843(4) 1.0987(2) 0.0790(16) Uani 1 1 d . . . . .
H9A H 0.5262 0.9686 1.1423 0.119 Uiso 1 1 calc R U . . .
H9B H 0.4203 1.0298 1.0924 0.119 Uiso 1 1 calc R U . . .
H9C H 0.5957 1.0327 1.0832 0.119 Uiso 1 1 calc R U . . .
C10 C 0.5107(5) 1.0599(3) 0.95210(19) 0.0442(10) Uani 1 1 d . . . . .
H10 H 0.4875 1.0878 0.9944 0.053 Uiso 1 1 calc R U . . .
C11 C 0.4160(5) 1.1391(3) 0.9076(2) 0.0579(12) Uani 1 1 d . . . . .
H11A H 0.4341 1.1116 0.8652 0.069 Uiso 1 1 calc R U . . .
H11B H 0.3100 1.1267 0.9167 0.069 Uiso 1 1 calc R U . . .
C12 C 0.4539(5) 1.2778(4) 0.9131(2) 0.0617(13) Uani 1 1 d . . . . .
H12A H 0.3952 1.3251 0.8831 0.074 Uiso 1 1 calc R U . . .
H12B H 0.4281 1.3074 0.9544 0.074 Uiso 1 1 calc R U . . .
C13 C 0.6207(6) 1.2983(4) 0.9012(2) 0.0653(14) Uani 1 1 d . . . . .
H13A H 0.6445 1.2745 0.8588 0.078 Uiso 1 1 calc R U . . .
H13B H 0.6443 1.3866 0.9061 0.078 Uiso 1 1 calc R U . . .
C14 C 0.7143(6) 1.2233(4) 0.9451(2) 0.0676(14) Uani 1 1 d . . . . .
H14A H 0.6971 1.2523 0.9872 0.081 Uiso 1 1 calc R U . . .
H14B H 0.8202 1.2356 0.9354 0.081 Uiso 1 1 calc R U . . .
C15 C 0.6768(5) 1.0850(4) 0.9408(2) 0.0592(13) Uani 1 1 d . . . . .
H15A H 0.7359 1.0394 0.9713 0.071 Uiso 1 1 calc R U . . .
H15B H 0.7042 1.0543 0.8999 0.071 Uiso 1 1 calc R U . . .
C16 C 0.5934(5) 0.6667(4) 0.77704(19) 0.0511(10) Uani 1 1 d . . . . .
C17 C 0.6613(6) 0.7728(4) 0.7527(2) 0.0607(13) Uani 1 1 d . . . . .
H17 H 0.6123 0.8498 0.7540 0.073 Uiso 1 1 calc R U . . .
C18 C 0.8011(7) 0.7628(5) 0.7267(2) 0.0696(15) Uani 1 1 d . . . . .
H18 H 0.8461 0.8343 0.7103 0.084 Uiso 1 1 calc R U . . .
C19 C 0.8780(6) 0.6508(5) 0.7237(2) 0.0698(14) Uani 1 1 d . . . . .
C20 C 0.8064(6) 0.5455(5) 0.7478(2) 0.0642(13) Uani 1 1 d . . . . .
H20 H 0.8536 0.4678 0.7452 0.077 Uiso 1 1 calc R U . . .
C21 C 0.6680(6) 0.5543(4) 0.7753(2) 0.0581(12) Uani 1 1 d . . . . .
H21 H 0.6241 0.4836 0.7930 0.070 Uiso 1 1 calc R U . . .
C22 C 1.0289(6) 0.6405(6) 0.6925(3) 0.112(2) Uani 1 1 d . . . . .
H22A H 1.0588 0.7213 0.6772 0.168 Uiso 1 1 calc R U . . .
H22B H 1.0223 0.5826 0.6584 0.168 Uiso 1 1 calc R U . . .
H22C H 1.1022 0.6109 0.7219 0.168 Uiso 1 1 calc R U . . .


_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 1.428(3) . ?
S1 O2 1.431(3) . ?
S1 N1 1.623(4) . ?
S1 C16 1.766(5) . ?
N1 C7 1.458(5) . ?
N1 C8 1.471(5) . ?
C1 C8 1.509(6) . ?
C1 C5 1.511(5) . ?
C1 C2 1.546(6) . ?
C1 H1 0.9800 . ?
C2 C3 1.482(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.325(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.473(6) . ?
C4 C9 1.492(6) . ?
C5 C6 1.336(5) . ?
C6 C7 1.505(6) . ?
C6 C10 1.528(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.517(6) . ?
C10 C11 1.528(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.521(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.517(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.490(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.515(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.369(6) . ?
C16 C17 1.385(6) . ?
C17 C18 1.364(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(7) . ?
C19 C22 1.502(7) . ?
C20 C21 1.366(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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 119.6(2) . . ?
O1 S1 N1 107.3(2) . . ?
O2 S1 N1 106.02(18) . . ?
O1 S1 C16 107.59(19) . . ?
O2 S1 C16 107.8(2) . . ?
N1 S1 C16 108.1(2) . . ?
C7 N1 C8 115.7(4) . . ?
C7 N1 S1 116.5(3) . . ?
C8 N1 S1 117.5(3) . . ?
C8 C1 C5 111.7(3) . . ?
C8 C1 C2 116.2(4) . . ?
C5 C1 C2 103.6(4) . . ?
C8 C1 H1 108.4 . . ?
C5 C1 H1 108.4 . . ?
C2 C1 H1 108.4 . . ?
C3 C2 C1 102.3(4) . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2B 111.3 . . ?
C1 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C4 C3 C2 113.7(4) . . ?
C4 C3 H3 123.2 . . ?
C2 C3 H3 123.2 . . ?
C3 C4 C5 109.1(4) . . ?
C3 C4 C9 123.1(4) . . ?
C5 C4 C9 127.7(4) . . ?
C6 C5 C4 132.6(4) . . ?
C6 C5 C1 121.0(4) . . ?
C4 C5 C1 106.2(4) . . ?
C5 C6 C7 121.3(4) . . ?
C5 C6 C10 124.7(4) . . ?
C7 C6 C10 113.8(3) . . ?
N1 C7 C6 114.2(4) . . ?
N1 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C1 106.7(3) . . ?
N1 C8 H8A 110.4 . . ?
C1 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C1 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 109.6(4) . . ?
C15 C10 C6 110.8(3) . . ?
C11 C10 C6 114.0(3) . . ?
C15 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C6 C10 H10 107.4 . . ?
C12 C11 C10 111.6(4) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 110.0(4) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 111.1(4) . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 111.3(4) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C10 112.1(4) . . ?
C14 C15 H15A 109.2 . . ?
C10 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C10 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C21 C16 C17 119.6(4) . . ?
C21 C16 S1 120.2(3) . . ?
C17 C16 S1 120.1(4) . . ?
C18 C17 C16 119.1(4) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 122.4(5) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C20 117.2(5) . . ?
C18 C19 C22 121.7(5) . . ?
C20 C19 C22 121.0(5) . . ?
C21 C20 C19 121.1(5) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C16 120.4(4) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C7 -168.9(3) . . . . ?
O2 S1 N1 C7 -40.0(4) . . . . ?
C16 S1 N1 C7 75.3(4) . . . . ?
O1 S1 N1 C8 47.3(4) . . . . ?
O2 S1 N1 C8 176.2(3) . . . . ?
C16 S1 N1 C8 -68.5(4) . . . . ?
C8 C1 C2 C3 144.1(4) . . . . ?
C5 C1 C2 C3 21.2(5) . . . . ?
C1 C2 C3 C4 -14.7(6) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
C2 C3 C4 C9 -175.6(4) . . . . ?
C3 C4 C5 C6 -160.7(5) . . . . ?
C9 C4 C5 C6 15.9(8) . . . . ?
C3 C4 C5 C1 13.3(5) . . . . ?
C9 C4 C5 C1 -170.1(4) . . . . ?
C8 C1 C5 C6 27.7(6) . . . . ?
C2 C1 C5 C6 153.4(4) . . . . ?
C8 C1 C5 C4 -147.2(4) . . . . ?
C2 C1 C5 C4 -21.4(5) . . . . ?
C4 C5 C6 C7 172.2(5) . . . . ?
C1 C5 C6 C7 -1.1(6) . . . . ?
C4 C5 C6 C10 -2.1(8) . . . . ?
C1 C5 C6 C10 -175.4(4) . . . . ?
C8 N1 C7 C6 -35.2(6) . . . . ?
S1 N1 C7 C6 -179.7(3) . . . . ?
C5 C6 C7 N1 3.8(6) . . . . ?
C10 C6 C7 N1 178.7(4) . . . . ?
C7 N1 C8 C1 60.5(5) . . . . ?
S1 N1 C8 C1 -155.4(3) . . . . ?
C5 C1 C8 N1 -54.5(5) . . . . ?
C2 C1 C8 N1 -173.1(4) . . . . ?
C5 C6 C10 C15 93.6(5) . . . . ?
C7 C6 C10 C15 -81.1(5) . . . . ?
C5 C6 C10 C11 -142.2(4) . . . . ?
C7 C6 C10 C11 43.1(5) . . . . ?
C15 C10 C11 C12 -55.4(5) . . . . ?
C6 C10 C11 C12 179.7(4) . . . . ?
C10 C11 C12 C13 57.0(5) . . . . ?
C11 C12 C13 C14 -57.3(5) . . . . ?
C12 C13 C14 C15 56.8(5) . . . . ?
C13 C14 C15 C10 -56.1(6) . . . . ?
C11 C10 C15 C14 54.6(5) . . . . ?
C6 C10 C15 C14 -178.7(4) . . . . ?
O1 S1 C16 C21 -14.5(4) . . . . ?
O2 S1 C16 C21 -144.7(4) . . . . ?
N1 S1 C16 C21 101.1(4) . . . . ?
O1 S1 C16 C17 166.4(3) . . . . ?
O2 S1 C16 C17 36.1(4) . . . . ?
N1 S1 C16 C17 -78.1(4) . . . . ?
C21 C16 C17 C18 0.8(7) . . . . ?
S1 C16 C17 C18 179.9(4) . . . . ?
C16 C17 C18 C19 -0.1(8) . . . . ?
C17 C18 C19 C20 0.8(8) . . . . ?
C17 C18 C19 C22 177.4(5) . . . . ?
C18 C19 C20 C21 -2.3(7) . . . . ?
C22 C19 C20 C21 -178.9(5) . . . . ?
C19 C20 C21 C16 3.1(7) . . . . ?
C17 C16 C21 C20 -2.3(7) . . . . ?
S1 C16 C21 C20 178.6(4) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_mo_d8v18422_0m
_database_code_depnum_ccdc_archive 'CCDC 1845295'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2018-05-25 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 N O2 S'
_chemical_formula_weight         329.44

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

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

_cell_length_a                   35.164(3)
_cell_length_b                   8.6573(6)
_cell_length_c                   11.5114(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.241(2)
_cell_angle_gamma                90
_cell_volume                     3494.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2512
_cell_measurement_theta_min      4.646
_cell_measurement_theta_max      51.631

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6205
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10407
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.323
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3190
_reflns_number_gt                2042
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+1.9104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3190
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.008
_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_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 0.65675(2) 0.90241(10) 0.78867(6) 0.0681(3) Uani 1 1 d . . . . .
O1 O 0.64416(6) 1.0587(3) 0.7923(2) 0.0901(7) Uani 1 1 d . . . . .
O2 O 0.66367(6) 0.8175(3) 0.89428(16) 0.0874(7) Uani 1 1 d . . . . .
N1 N 0.62494(6) 0.8053(3) 0.70852(18) 0.0622(6) Uani 1 1 d . . . . .
C1 C 0.61094(8) 0.8758(4) 0.5965(2) 0.0685(8) Uani 1 1 d . . . . .
H1A H 0.6289 0.8564 0.5382 0.082 Uiso 1 1 calc R U . . .
H1B H 0.6085 0.9867 0.6057 0.082 Uiso 1 1 calc R U . . .
C2 C 0.57238(8) 0.8063(4) 0.5575(3) 0.0719(9) Uani 1 1 d . . . . .
C3 C 0.55994(10) 0.8383(5) 0.4288(3) 0.1022(13) Uani 1 1 d . . . . .
H3A H 0.5819 0.8545 0.3842 0.123 Uiso 1 1 calc R U . . .
H3B H 0.5437 0.9289 0.4214 0.123 Uiso 1 1 calc R U . . .
C4 C 0.53778(11) 0.6924(6) 0.3863(3) 0.1222(16) Uani 1 1 d . . . . .
H4A H 0.5109 0.7021 0.3989 0.147 Uiso 1 1 calc R U . . .
H4B H 0.5404 0.6747 0.3041 0.147 Uiso 1 1 calc R U . . .
C5 C 0.55567(10) 0.5640(6) 0.4582(3) 0.0955(12) Uani 1 1 d . . . . .
C6 C 0.55664(13) 0.4117(7) 0.4416(4) 0.1192(17) Uani 1 1 d . . . . .
H6 H 0.5444 0.3684 0.3749 0.143 Uiso 1 1 calc R U . . .
C7 C 0.57746(13) 0.3107(6) 0.5304(5) 0.1220(16) Uani 1 1 d . . . . .
H7A H 0.5873 0.2218 0.4911 0.146 Uiso 1 1 calc R U . . .
H7B H 0.5594 0.2731 0.5836 0.146 Uiso 1 1 calc R U . . .
C8 C 0.61000(10) 0.3882(4) 0.6002(3) 0.0954(11) Uani 1 1 d . . . . .
H8A H 0.6143 0.3349 0.6741 0.114 Uiso 1 1 calc R U . . .
H8B H 0.6329 0.3774 0.5588 0.114 Uiso 1 1 calc R U . . .
C9 C 0.60370(8) 0.5558(4) 0.6234(3) 0.0671(8) Uani 1 1 d . . . . .
C10 C 0.57759(8) 0.6347(4) 0.5578(2) 0.0694(8) Uani 1 1 d . . . . .
C11 C 0.63067(8) 0.6367(4) 0.7087(2) 0.0686(8) Uani 1 1 d . . . . .
H11A H 0.6274 0.5970 0.7862 0.082 Uiso 1 1 calc R U . . .
H11B H 0.6566 0.6145 0.6904 0.082 Uiso 1 1 calc R U . . .
C12 C 0.54190(9) 0.8606(5) 0.6384(3) 0.0969(12) Uani 1 1 d . . . . .
H12A H 0.5499 0.8348 0.7175 0.145 Uiso 1 1 calc R U . . .
H12B H 0.5181 0.8105 0.6164 0.145 Uiso 1 1 calc R U . . .
H12C H 0.5387 0.9705 0.6315 0.145 Uiso 1 1 calc R U . . .
C13 C 0.69900(8) 0.9022(3) 0.7163(2) 0.0561(7) Uani 1 1 d . . . . .
C14 C 0.70240(8) 0.9953(3) 0.6202(2) 0.0634(8) Uani 1 1 d . . . . .
H14 H 0.6823 1.0593 0.5940 0.076 Uiso 1 1 calc R U . . .
C15 C 0.73525(9) 0.9936(4) 0.5636(2) 0.0689(8) Uani 1 1 d . . . . .
H15 H 0.7370 1.0554 0.4981 0.083 Uiso 1 1 calc R U . . .
C16 C 0.76608(9) 0.9016(4) 0.6017(3) 0.0688(8) Uani 1 1 d . . . . .
C17 C 0.76225(9) 0.8093(4) 0.6971(3) 0.0741(9) Uani 1 1 d . . . . .
H17 H 0.7825 0.7467 0.7239 0.089 Uiso 1 1 calc R U . . .
C18 C 0.72921(9) 0.8071(4) 0.7539(2) 0.0682(8) Uani 1 1 d . . . . .
H18 H 0.7271 0.7421 0.8174 0.082 Uiso 1 1 calc R U . . .
C19 C 0.80225(10) 0.9040(5) 0.5399(3) 0.0997(12) Uani 1 1 d . . . . .
H19A H 0.7973 0.8642 0.4624 0.150 Uiso 1 1 calc R U . . .
H19B H 0.8211 0.8412 0.5817 0.150 Uiso 1 1 calc R U . . .
H19C H 0.8114 1.0083 0.5361 0.150 Uiso 1 1 calc R U . . .


_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 1.425(2) . ?
S1 O2 1.426(2) . ?
S1 N1 1.630(2) . ?
S1 C13 1.757(3) . ?
N1 C11 1.474(4) . ?
N1 C1 1.478(3) . ?
C1 C2 1.521(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C10 1.497(4) . ?
C2 C3 1.538(4) . ?
C2 C12 1.544(4) . ?
C3 C4 1.544(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.496(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.334(6) . ?
C5 C10 1.467(5) . ?
C6 C7 1.495(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.506(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.496(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.333(4) . ?
C9 C11 1.488(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.381(4) . ?
C13 C18 1.388(4) . ?
C14 C15 1.368(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(4) . ?
C16 C19 1.503(4) . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 119.86(14) . . ?
O1 S1 N1 107.73(14) . . ?
O2 S1 N1 106.48(13) . . ?
O1 S1 C13 106.89(14) . . ?
O2 S1 C13 107.87(14) . . ?
N1 S1 C13 107.46(12) . . ?
C11 N1 C1 116.6(2) . . ?
C11 N1 S1 114.95(19) . . ?
C1 N1 S1 116.84(19) . . ?
N1 C1 C2 109.1(2) . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C10 C2 C1 106.6(2) . . ?
C10 C2 C3 102.0(3) . . ?
C1 C2 C3 113.4(2) . . ?
C10 C2 C12 113.0(3) . . ?
C1 C2 C12 110.2(3) . . ?
C3 C2 C12 111.4(3) . . ?
C2 C3 C4 105.0(3) . . ?
C2 C3 H3A 110.7 . . ?
C4 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C5 C4 C3 104.5(3) . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C6 C5 C10 120.5(4) . . ?
C6 C5 C4 132.0(4) . . ?
C10 C5 C4 107.4(4) . . ?
C5 C6 C7 119.7(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 114.8(4) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 114.2(3) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C11 120.8(3) . . ?
C10 C9 C8 120.0(3) . . ?
C11 C9 C8 118.6(3) . . ?
C9 C10 C5 122.0(4) . . ?
C9 C10 C2 126.1(3) . . ?
C5 C10 C2 110.7(3) . . ?
N1 C11 C9 112.6(3) . . ?
N1 C11 H11A 109.1 . . ?
C9 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C9 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 119.1(3) . . ?
C14 C13 S1 120.4(2) . . ?
C18 C13 S1 120.5(2) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 121.5(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 117.8(3) . . ?
C17 C16 C19 121.6(3) . . ?
C15 C16 C19 120.6(3) . . ?
C16 C17 C18 121.7(3) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C13 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_d8v18866
_database_code_depnum_ccdc_archive 'CCDC 1875219'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2018-10-25 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H33 N O2 S'
_chemical_formula_weight         387.56

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   19.505(3)
_cell_length_b                   8.6857(13)
_cell_length_c                   13.1687(16)
_cell_angle_alpha                90
_cell_angle_beta                 92.309(4)
_cell_angle_gamma                90
_cell_volume                     2229.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8221
_cell_measurement_theta_min      4.475
_cell_measurement_theta_max      54.762

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5844
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24173
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.567
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4380
_reflns_number_gt                2654
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²+0.7717P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4380
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1912
_refine_ls_wR_factor_gt          0.1559
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_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_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 0.35138(4) 0.33324(10) 0.18342(6) 0.0725(3) Uani 1 1 d . . . . .
O1 O 0.32286(11) 0.1826(3) 0.17692(18) 0.0845(7) Uani 1 1 d . . . . .
O2 O 0.37288(12) 0.4095(3) 0.09386(16) 0.0991(8) Uani 1 1 d . . . . .
N1 N 0.29366(11) 0.4440(3) 0.23145(18) 0.0661(6) Uani 1 1 d . . . . .
C1 C 0.25464(13) 0.3816(3) 0.3155(2) 0.0641(7) Uani 1 1 d . . . . .
H1A H 0.2856 0.3643 0.3739 0.077 Uiso 1 1 calc R U . . .
H1B H 0.2350 0.2831 0.2954 0.077 Uiso 1 1 calc R U . . .
C2 C 0.19809(14) 0.4884(3) 0.3452(2) 0.0620(7) Uani 1 1 d . . . . .
C3 C 0.19502(16) 0.6315(4) 0.3098(2) 0.0720(8) Uani 1 1 d . . . . .
C4 C 0.1487(2) 0.7612(5) 0.3432(3) 0.1076(14) Uani 1 1 d . . . . .
H4 H 0.1479 0.7595 0.4175 0.129 Uiso 1 1 calc R U . . .
C5 C 0.1871(3) 0.9080(5) 0.3112(4) 0.150(2) Uani 1 1 d . . . . .
H5A H 0.1633 0.9559 0.2534 0.180 Uiso 1 1 calc R U . . .
H5B H 0.1895 0.9813 0.3668 0.180 Uiso 1 1 calc R U . . .
C6 C 0.2576(3) 0.8608(5) 0.2839(4) 0.1294(16) Uani 1 1 d . . . . .
H6A H 0.2885 0.8581 0.3434 0.155 Uiso 1 1 calc R U . . .
H6B H 0.2759 0.9303 0.2341 0.155 Uiso 1 1 calc R U . . .
C7 C 0.24652(19) 0.6992(4) 0.2393(3) 0.0815(9) Uani 1 1 d . . . . .
C8 C 0.31152(16) 0.6071(4) 0.2451(3) 0.0807(9) Uani 1 1 d . . . . .
H8A H 0.3417 0.6398 0.1924 0.097 Uiso 1 1 calc R U . . .
H8B H 0.3351 0.6224 0.3106 0.097 Uiso 1 1 calc R U . . .
C9 C 0.2177(2) 0.7023(5) 0.1284(3) 0.1083(13) Uani 1 1 d . . . . .
H9A H 0.2126 0.5988 0.1037 0.162 Uiso 1 1 calc R U . . .
H9B H 0.2488 0.7574 0.0869 0.162 Uiso 1 1 calc R U . . .
H9C H 0.1739 0.7527 0.1256 0.162 Uiso 1 1 calc R U . . .
C10 C 0.0769(3) 0.7536(7) 0.3021(4) 0.167(2) Uani 1 1 d . . . . .
H10A H 0.0765 0.7547 0.2291 0.251 Uiso 1 1 calc R U . . .
H10B H 0.0518 0.8407 0.3257 0.251 Uiso 1 1 calc R U . . .
H10C H 0.0558 0.6604 0.3247 0.251 Uiso 1 1 calc R U . . .
C11 C 0.14896(15) 0.4214(4) 0.4197(2) 0.0682(8) Uani 1 1 d . . . . .
H11 H 0.1239 0.5080 0.4484 0.082 Uiso 1 1 calc R U . . .
C12 C 0.18469(18) 0.3367(4) 0.5087(2) 0.0864(10) Uani 1 1 d . . . . .
H12A H 0.2114 0.2522 0.4829 0.104 Uiso 1 1 calc R U . . .
H12B H 0.2160 0.4067 0.5445 0.104 Uiso 1 1 calc R U . . .
C13 C 0.1333(2) 0.2741(6) 0.5827(3) 0.1110(13) Uani 1 1 d . . . . .
H13A H 0.1577 0.2169 0.6362 0.133 Uiso 1 1 calc R U . . .
H13B H 0.1099 0.3593 0.6139 0.133 Uiso 1 1 calc R U . . .
C14 C 0.0819(2) 0.1720(5) 0.5309(3) 0.1121(14) Uani 1 1 d . . . . .
H14A H 0.0486 0.1393 0.5792 0.134 Uiso 1 1 calc R U . . .
H14B H 0.1048 0.0809 0.5063 0.134 Uiso 1 1 calc R U . . .
C15 C 0.04548(19) 0.2521(5) 0.4432(3) 0.1093(13) Uani 1 1 d . . . . .
H15A H 0.0181 0.3357 0.4688 0.131 Uiso 1 1 calc R U . . .
H15B H 0.0147 0.1801 0.4083 0.131 Uiso 1 1 calc R U . . .
C16 C 0.09592(15) 0.3159(4) 0.3682(2) 0.0822(10) Uani 1 1 d . . . . .
H16A H 0.1192 0.2311 0.3363 0.099 Uiso 1 1 calc R U . . .
H16B H 0.0708 0.3727 0.3153 0.099 Uiso 1 1 calc R U . . .
C17 C 0.42168(13) 0.3283(3) 0.2714(2) 0.0640(7) Uani 1 1 d . . . . .
C18 C 0.47786(16) 0.4210(4) 0.2581(3) 0.0840(9) Uani 1 1 d . . . . .
H18 H 0.4796 0.4839 0.2011 0.101 Uiso 1 1 calc R U . . .
C19 C 0.53154(17) 0.4204(5) 0.3293(3) 0.0976(11) Uani 1 1 d . . . . .
H19 H 0.5694 0.4829 0.3194 0.117 Uiso 1 1 calc R U . . .
C20 C 0.53064(17) 0.3302(5) 0.4143(3) 0.0891(11) Uani 1 1 d . . . . .
C21 C 0.47389(18) 0.2369(4) 0.4272(3) 0.0875(10) Uani 1 1 d . . . . .
H21 H 0.4723 0.1747 0.4845 0.105 Uiso 1 1 calc R U . . .
C22 C 0.41989(15) 0.2348(4) 0.3567(3) 0.0761(9) Uani 1 1 d . . . . .
H22 H 0.3824 0.1710 0.3662 0.091 Uiso 1 1 calc R U . . .
C23 C 0.5889(2) 0.3322(6) 0.4932(3) 0.1356(18) Uani 1 1 d . . . . .
H23A H 0.5734 0.3771 0.5548 0.203 Uiso 1 1 calc R U . . .
H23B H 0.6261 0.3920 0.4687 0.203 Uiso 1 1 calc R U . . .
H23C H 0.6042 0.2288 0.5064 0.203 Uiso 1 1 calc R U . . .


_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 1.423(2) . ?
S1 O2 1.430(2) . ?
S1 N1 1.628(2) . ?
S1 C17 1.760(3) . ?
N1 C8 1.468(4) . ?
N1 C1 1.472(3) . ?
C1 C2 1.505(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.328(4) . ?
C2 C11 1.515(4) . ?
C3 C7 1.514(4) . ?
C3 C4 1.521(4) . ?
C4 C10 1.483(6) . ?
C4 C5 1.546(6) . ?
C4 H4 0.9800 . ?
C5 C6 1.492(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.533(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.499(4) . ?
C7 C9 1.544(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.521(4) . ?
C11 C12 1.528(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.527(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.484(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.502(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.527(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.377(4) . ?
C17 C22 1.388(4) . ?
C18 C19 1.378(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(5) . ?
C20 C23 1.509(5) . ?
C21 C22 1.375(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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 120.21(15) . . ?
O1 S1 N1 106.96(12) . . ?
O2 S1 N1 106.10(14) . . ?
O1 S1 C17 108.03(14) . . ?
O2 S1 C17 107.92(14) . . ?
N1 S1 C17 106.92(13) . . ?
C8 N1 C1 113.0(2) . . ?
C8 N1 S1 116.95(19) . . ?
C1 N1 S1 117.48(18) . . ?
N1 C1 C2 112.0(2) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 C11 124.5(3) . . ?
C1 C2 C11 114.9(2) . . ?
C2 C3 C7 123.9(3) . . ?
C2 C3 C4 127.6(3) . . ?
C7 C3 C4 107.8(3) . . ?
C10 C4 C3 115.1(4) . . ?
C10 C4 C5 113.5(4) . . ?
C3 C4 C5 103.4(3) . . ?
C10 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C6 C5 C4 107.5(4) . . ?
C6 C5 H5A 110.2 . . ?
C4 C5 H5A 110.2 . . ?
C6 C5 H5B 110.2 . . ?
C4 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
C5 C6 C7 103.1(4) . . ?
C5 C6 H6A 111.1 . . ?
C7 C6 H6A 111.1 . . ?
C5 C6 H6B 111.1 . . ?
C7 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C3 110.0(3) . . ?
C8 C7 C6 111.3(3) . . ?
C3 C7 C6 102.0(3) . . ?
C8 C7 C9 109.4(3) . . ?
C3 C7 C9 111.2(3) . . ?
C6 C7 C9 112.7(3) . . ?
N1 C8 C7 108.2(3) . . ?
N1 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
N1 C8 H8B 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 C16 112.2(2) . . ?
C2 C11 C12 113.6(2) . . ?
C16 C11 C12 109.5(3) . . ?
C2 C11 H11 107.0 . . ?
C16 C11 H11 107.0 . . ?
C12 C11 H11 107.0 . . ?
C13 C12 C11 111.7(3) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 111.6(3) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 111.5(4) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 111.6(3) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C11 C16 C15 112.0(3) . . ?
C11 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C11 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 C22 119.5(3) . . ?
C18 C17 S1 120.3(2) . . ?
C22 C17 S1 120.2(2) . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 121.7(3) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 118.1(3) . . ?
C19 C20 C23 121.5(4) . . ?
C21 C20 C23 120.3(4) . . ?
C22 C21 C20 121.3(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C17 119.6(3) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C8 -179.7(2) . . . . ?
O2 S1 N1 C8 -50.3(2) . . . . ?
C17 S1 N1 C8 64.7(2) . . . . ?
O1 S1 N1 C1 41.0(2) . . . . ?
O2 S1 N1 C1 170.4(2) . . . . ?
C17 S1 N1 C1 -74.6(2) . . . . ?
C8 N1 C1 C2 45.3(3) . . . . ?
S1 N1 C1 C2 -173.83(19) . . . . ?
N1 C1 C2 C3 -11.5(4) . . . . ?
N1 C1 C2 C11 170.9(2) . . . . ?
C1 C2 C3 C7 -0.5(4) . . . . ?
C11 C2 C3 C7 176.9(3) . . . . ?
C1 C2 C3 C4 -170.1(3) . . . . ?
C11 C2 C3 C4 7.3(5) . . . . ?
C2 C3 C4 C10 -78.4(5) . . . . ?
C7 C3 C4 C10 110.6(4) . . . . ?
C2 C3 C4 C5 157.2(4) . . . . ?
C7 C3 C4 C5 -13.7(4) . . . . ?
C10 C4 C5 C6 -137.6(4) . . . . ?
C3 C4 C5 C6 -12.1(5) . . . . ?
C4 C5 C6 C7 32.8(5) . . . . ?
C2 C3 C7 C8 -19.7(4) . . . . ?
C4 C3 C7 C8 151.7(3) . . . . ?
C2 C3 C7 C6 -137.9(3) . . . . ?
C4 C3 C7 C6 33.5(4) . . . . ?
C2 C3 C7 C9 101.7(4) . . . . ?
C4 C3 C7 C9 -86.9(3) . . . . ?
C5 C6 C7 C8 -157.4(3) . . . . ?
C5 C6 C7 C3 -40.1(4) . . . . ?
C5 C6 C7 C9 79.2(4) . . . . ?
C1 N1 C8 C7 -66.5(3) . . . . ?
S1 N1 C8 C7 152.5(2) . . . . ?
C3 C7 C8 N1 50.6(3) . . . . ?
C6 C7 C8 N1 162.8(3) . . . . ?
C9 C7 C8 N1 -71.9(3) . . . . ?
C3 C2 C11 C16 103.1(3) . . . . ?
C1 C2 C11 C16 -79.4(3) . . . . ?
C3 C2 C11 C12 -132.1(3) . . . . ?
C1 C2 C11 C12 45.5(3) . . . . ?
C2 C11 C12 C13 178.9(3) . . . . ?
C16 C11 C12 C13 -54.7(4) . . . . ?
C11 C12 C13 C14 56.2(5) . . . . ?
C12 C13 C14 C15 -55.7(5) . . . . ?
C13 C14 C15 C16 55.1(5) . . . . ?
C2 C11 C16 C15 -178.6(3) . . . . ?
C12 C11 C16 C15 54.3(4) . . . . ?
C14 C15 C16 C11 -55.0(5) . . . . ?
O1 S1 C17 C18 146.6(3) . . . . ?
O2 S1 C17 C18 15.1(3) . . . . ?
N1 S1 C17 C18 -98.6(3) . . . . ?
O1 S1 C17 C22 -35.7(3) . . . . ?
O2 S1 C17 C22 -167.1(2) . . . . ?
N1 S1 C17 C22 79.2(3) . . . . ?
C22 C17 C18 C19 -0.1(5) . . . . ?
S1 C17 C18 C19 177.7(3) . . . . ?
C17 C18 C19 C20 -0.4(5) . . . . ?
C18 C19 C20 C21 0.5(5) . . . . ?
C18 C19 C20 C23 -178.7(3) . . . . ?
C19 C20 C21 C22 0.0(5) . . . . ?
C23 C20 C21 C22 179.2(3) . . . . ?
C20 C21 C22 C17 -0.5(5) . . . . ?
C18 C17 C22 C21 0.6(5) . . . . ?
S1 C17 C22 C21 -177.2(2) . . . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cd17159
_database_code_depnum_ccdc_archive 'CCDC 1540623'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H26 Br N O2 S'
_chemical_formula_weight         436.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

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

_cell_length_a                   10.888(3)
_cell_length_b                   8.651(2)
_cell_length_c                   10.910(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.500(5)
_cell_angle_gamma                90
_cell_volume                     1018.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1772
_cell_measurement_theta_min      4.971
_cell_measurement_theta_max      40.047

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.135
_shelx_estimated_absorpt_T_min   0.675
_shelx_estimated_absorpt_T_max   0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5762
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5861
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.883
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3723
_reflns_number_gt                2766
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.969

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.0566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1058 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.037(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3723
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_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
Br1 Br -0.12768(8) 1.41885(10) 0.19788(8) 0.1010(4) Uani 1 1 d . . . . .
S1 S 0.14591(13) 0.76913(19) 0.28600(13) 0.0547(4) Uani 1 1 d . . . . .
N1 N 0.2886(4) 0.8037(6) 0.3440(4) 0.0512(12) Uani 1 1 d . . . . .
O1 O 0.0890(4) 0.6922(6) 0.3795(4) 0.0711(12) Uani 1 1 d . . . . .
O2 O 0.1501(4) 0.6994(5) 0.1687(4) 0.0679(12) Uani 1 1 d . . . . .
C1 C 0.3110(5) 0.8730(7) 0.4681(5) 0.0544(15) Uani 1 1 d . . . . .
H1A H 0.2484 0.8391 0.5178 0.065 Uiso 1 1 calc R U . . .
H1B H 0.3082 0.9848 0.4624 0.065 Uiso 1 1 calc R U . . .
C2 C 0.4364(5) 0.8207(7) 0.5250(5) 0.0465(13) Uani 1 1 d . . . . .
H2 H 0.4328 0.7102 0.5440 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4911(6) 0.9071(10) 0.6416(5) 0.0635(16) Uani 1 1 d . . . . .
H3A H 0.4727 1.0167 0.6350 0.076 Uiso 1 1 calc R U . . .
H3B H 0.4599 0.8660 0.7143 0.076 Uiso 1 1 calc R U . . .
C4 C 0.6265(7) 0.8782(9) 0.6463(6) 0.070(2) Uani 1 1 d . . . . .
H4A H 0.6732 0.9652 0.6842 0.084 Uiso 1 1 calc R U . . .
H4B H 0.6500 0.7863 0.6948 0.084 Uiso 1 1 calc R U . . .
C5 C 0.6524(6) 0.8573(7) 0.5200(5) 0.0535(15) Uani 1 1 d . . . . .
C6 C 0.5328(5) 0.8459(6) 0.4397(5) 0.0419(12) Uani 1 1 d . . . . .
C7 C 0.5041(5) 0.8709(6) 0.3192(5) 0.0430(12) Uani 1 1 d . . . . .
C8 C 0.3708(5) 0.8625(8) 0.2595(5) 0.0526(15) Uani 1 1 d . . . . .
H8A H 0.3436 0.9649 0.2317 0.063 Uiso 1 1 calc R U . . .
H8B H 0.3656 0.7958 0.1875 0.063 Uiso 1 1 calc R U . . .
C9 C 0.7686(6) 0.8427(11) 0.4892(7) 0.084(2) Uani 1 1 d . . . . .
H9A H 0.8366 0.8459 0.5504 0.100 Uiso 1 1 calc R U . . .
H9B H 0.7803 0.8295 0.4069 0.100 Uiso 1 1 calc R U . . .
C10 C 0.5957(4) 0.9059(7) 0.2309(4) 0.0450(12) Uani 1 1 d . . . . .
H10 H 0.6687 0.9511 0.2800 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6386(6) 0.7600(8) 0.1734(6) 0.0646(16) Uani 1 1 d . . . . .
H11A H 0.5684 0.7107 0.1248 0.078 Uiso 1 1 calc R U . . .
H11B H 0.6712 0.6889 0.2384 0.078 Uiso 1 1 calc R U . . .
C12 C 0.7388(7) 0.7932(10) 0.0904(7) 0.083(2) Uani 1 1 d . . . . .
H12A H 0.8124 0.8315 0.1410 0.100 Uiso 1 1 calc R U . . .
H12B H 0.7605 0.6977 0.0520 0.100 Uiso 1 1 calc R U . . .
C13 C 0.6985(7) 0.9067(14) -0.0060(6) 0.083(2) Uani 1 1 d . . . . .
H13A H 0.6317 0.8634 -0.0633 0.100 Uiso 1 1 calc R U . . .
H13B H 0.7667 0.9303 -0.0518 0.100 Uiso 1 1 calc R U . . .
C14 C 0.6547(7) 1.0531(12) 0.0496(8) 0.094(3) Uani 1 1 d . . . . .
H14A H 0.6236 1.1240 -0.0161 0.113 Uiso 1 1 calc R U . . .
H14B H 0.7239 1.1023 0.0997 0.113 Uiso 1 1 calc R U . . .
C15 C 0.5536(6) 1.0201(9) 0.1287(6) 0.0673(18) Uani 1 1 d . . . . .
H15A H 0.4818 0.9788 0.0771 0.081 Uiso 1 1 calc R U . . .
H15B H 0.5292 1.1159 0.1650 0.081 Uiso 1 1 calc R U . . .
C16 C 0.0730(4) 0.9497(8) 0.2603(5) 0.0522(16) Uani 1 1 d . . . . .
C17 C 0.0679(5) 1.0223(9) 0.1479(5) 0.0626(17) Uani 1 1 d . . . . .
H17 H 0.1044 0.9762 0.0845 0.075 Uiso 1 1 calc R U . . .
C18 C 0.0094(6) 1.1626(9) 0.1282(6) 0.070(2) Uani 1 1 d . . . . .
H18 H 0.0056 1.2118 0.0520 0.084 Uiso 1 1 calc R U . . .
C19 C -0.0433(5) 1.2286(8) 0.2231(6) 0.0609(16) Uani 1 1 d . . . . .
C20 C -0.0392(6) 1.1572(9) 0.3353(6) 0.0667(19) Uani 1 1 d . . . . .
H20 H -0.0756 1.2037 0.3985 0.080 Uiso 1 1 calc R U . . .
C21 C 0.0186(5) 1.0173(8) 0.3543(5) 0.0582(16) Uani 1 1 d . . . . .
H21 H 0.0212 0.9679 0.4303 0.070 Uiso 1 1 calc R U . . .


_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
Br1 C19 1.888(7) . ?
S1 O2 1.421(4) . ?
S1 O1 1.426(5) . ?
S1 N1 1.627(5) . ?
S1 C16 1.758(7) . ?
N1 C8 1.459(7) . ?
N1 C1 1.471(7) . ?
C1 C2 1.495(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C6 1.507(7) . ?
C2 C3 1.527(8) . ?
C2 H2 0.9800 . ?
C3 C4 1.489(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.454(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C9 1.357(9) . ?
C5 C6 1.474(8) . ?
C6 C7 1.329(7) . ?
C7 C10 1.505(7) . ?
C7 C8 1.513(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?
C10 C11 1.510(9) . ?
C10 C15 1.515(8) . ?
C10 H10 0.9800 . ?
C11 C12 1.533(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.464(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.509(14) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.511(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.373(8) . ?
C16 C21 1.379(8) . ?
C17 C18 1.374(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.366(9) . ?
C20 C21 1.368(10) . ?
C20 H20 0.9300 . ?
C21 H21 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 121.0(3) . . ?
O2 S1 N1 106.7(2) . . ?
O1 S1 N1 106.8(2) . . ?
O2 S1 C16 107.5(3) . . ?
O1 S1 C16 107.4(3) . . ?
N1 S1 C16 106.7(3) . . ?
C8 N1 C1 113.5(4) . . ?
C8 N1 S1 116.9(3) . . ?
C1 N1 S1 117.9(3) . . ?
N1 C1 C2 106.9(4) . . ?
N1 C1 H1A 110.3 . . ?
C2 C1 H1A 110.3 . . ?
N1 C1 H1B 110.3 . . ?
C2 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
C1 C2 C6 111.8(4) . . ?
C1 C2 C3 115.7(5) . . ?
C6 C2 C3 102.5(4) . . ?
C1 C2 H2 108.8 . . ?
C6 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C4 C3 C2 102.9(5) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C5 C4 C3 107.5(5) . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C9 C5 C4 123.3(6) . . ?
C9 C5 C6 128.8(6) . . ?
C4 C5 C6 107.8(5) . . ?
C7 C6 C5 130.7(5) . . ?
C7 C6 C2 122.8(5) . . ?
C5 C6 C2 105.9(4) . . ?
C6 C7 C10 125.2(5) . . ?
C6 C7 C8 120.5(5) . . ?
C10 C7 C8 114.4(4) . . ?
N1 C8 C7 112.2(4) . . ?
N1 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C5 C9 H9A 120.0 . . ?
C5 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C7 C10 C11 111.4(5) . . ?
C7 C10 C15 116.1(5) . . ?
C11 C10 C15 108.7(5) . . ?
C7 C10 H10 106.7 . . ?
C11 C10 H10 106.7 . . ?
C15 C10 H10 106.7 . . ?
C10 C11 C12 111.8(6) . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 112.4(6) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 110.8(6) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 111.3(7) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C10 111.7(5) . . ?
C14 C15 H15A 109.3 . . ?
C10 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C10 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C21 119.9(6) . . ?
C17 C16 S1 120.9(5) . . ?
C21 C16 S1 119.1(5) . . ?
C16 C17 C18 120.5(6) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 118.7(6) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C20 C19 C18 121.3(7) . . ?
C20 C19 Br1 118.9(5) . . ?
C18 C19 Br1 119.8(5) . . ?
C19 C20 C21 119.7(6) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 119.8(6) . . ?
C20 C21 H21 120.1 . . ?
C16 C21 H21 120.1 . . ?

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 40.9(5) . . . . ?
O1 S1 N1 C8 171.6(4) . . . . ?
C16 S1 N1 C8 -73.7(5) . . . . ?
O2 S1 N1 C1 -178.5(4) . . . . ?
O1 S1 N1 C1 -47.8(5) . . . . ?
C16 S1 N1 C1 66.9(5) . . . . ?
C8 N1 C1 C2 -66.4(6) . . . . ?
S1 N1 C1 C2 151.7(4) . . . . ?
N1 C1 C2 C6 49.8(6) . . . . ?
N1 C1 C2 C3 166.7(5) . . . . ?
C1 C2 C3 C4 -158.1(5) . . . . ?
C6 C2 C3 C4 -36.1(6) . . . . ?
C2 C3 C4 C5 28.7(7) . . . . ?
C3 C4 C5 C9 173.8(7) . . . . ?
C3 C4 C5 C6 -9.6(7) . . . . ?
C9 C5 C6 C7 -25.7(11) . . . . ?
C4 C5 C6 C7 157.9(6) . . . . ?
C9 C5 C6 C2 162.5(7) . . . . ?
C4 C5 C6 C2 -13.9(6) . . . . ?
C1 C2 C6 C7 -17.0(7) . . . . ?
C3 C2 C6 C7 -141.6(6) . . . . ?
C1 C2 C6 C5 155.6(5) . . . . ?
C3 C2 C6 C5 31.0(6) . . . . ?
C5 C6 C7 C10 5.7(9) . . . . ?
C2 C6 C7 C10 176.3(5) . . . . ?
C5 C6 C7 C8 -175.5(6) . . . . ?
C2 C6 C7 C8 -4.9(8) . . . . ?
C1 N1 C8 C7 45.0(6) . . . . ?
S1 N1 C8 C7 -172.7(4) . . . . ?
C6 C7 C8 N1 -8.5(7) . . . . ?
C10 C7 C8 N1 170.5(5) . . . . ?
C6 C7 C10 C11 91.5(6) . . . . ?
C8 C7 C10 C11 -87.5(6) . . . . ?
C6 C7 C10 C15 -143.5(6) . . . . ?
C8 C7 C10 C15 37.6(7) . . . . ?
C7 C10 C11 C12 -175.9(5) . . . . ?
C15 C10 C11 C12 54.9(7) . . . . ?
C10 C11 C12 C13 -55.8(9) . . . . ?
C11 C12 C13 C14 54.5(9) . . . . ?
C12 C13 C14 C15 -55.5(9) . . . . ?
C13 C14 C15 C10 57.3(9) . . . . ?
C7 C10 C15 C14 177.1(7) . . . . ?
C11 C10 C15 C14 -56.5(8) . . . . ?
O2 S1 C16 C17 -21.3(6) . . . . ?
O1 S1 C16 C17 -152.9(5) . . . . ?
N1 S1 C16 C17 92.8(5) . . . . ?
O2 S1 C16 C21 157.7(4) . . . . ?
O1 S1 C16 C21 26.0(5) . . . . ?
N1 S1 C16 C21 -88.2(5) . . . . ?
C21 C16 C17 C18 0.3(9) . . . . ?
S1 C16 C17 C18 179.2(5) . . . . ?
C16 C17 C18 C19 0.2(9) . . . . ?
C17 C18 C19 C20 -0.4(9) . . . . ?
C17 C18 C19 Br1 -178.5(5) . . . . ?
C18 C19 C20 C21 0.1(9) . . . . ?
Br1 C19 C20 C21 178.2(5) . . . . ?
C19 C20 C21 C16 0.4(9) . . . . ?
C17 C16 C21 C20 -0.6(9) . . . . ?
S1 C16 C21 C20 -179.6(5) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_d8v18391
_database_code_depnum_ccdc_archive 'CCDC 1842625'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2018-05-11 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Br N O2 S'
_chemical_formula_weight         396.33

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'
Br Br -0.2901 2.4595 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   12.551(3)
_cell_length_b                   11.012(2)
_cell_length_c                   14.276(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.904(5)
_cell_angle_gamma                90
_cell_volume                     1804.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2444
_cell_measurement_theta_min      4.840
_cell_measurement_theta_max      47.122

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.403
_shelx_estimated_absorpt_T_min   0.714
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4416
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25856
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_av_R_equivalents  0.1817
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.564
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3162
_reflns_number_gt                1504
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1090P)²+2.4096P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3162
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1743
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2575
_refine_ls_wR_factor_gt          0.1987
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_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
Br1 Br 1.05176(10) 0.25228(9) 0.67071(8) 0.0900(6) Uani 1 1 d . . . . .
S1 S 0.5435(3) 0.7383(2) 0.2484(2) 0.0801(8) Uani 1 1 d . . . . .
O1 O 0.6046(7) 0.7936(7) 0.1932(7) 0.108(3) Uani 1 1 d . . . . .
O2 O 0.5037(7) 0.8104(6) 0.3096(6) 0.096(2) Uani 1 1 d . . . . .
N1 N 0.6307(6) 0.6358(6) 0.3245(5) 0.0578(18) Uani 1 1 d . . . . .
C1 C 0.6858(8) 0.5529(7) 0.2790(6) 0.061(2) Uani 1 1 d . . . . .
H1A H 0.7236 0.5994 0.2434 0.073 Uiso 1 1 calc R U . . .
H1B H 0.6264 0.5028 0.2288 0.073 Uiso 1 1 calc R U . . .
C2 C 0.7749(7) 0.4718(7) 0.3569(6) 0.0474(19) Uani 1 1 d . . . . .
C3 C 0.7866(6) 0.4689(6) 0.4536(6) 0.0451(19) Uani 1 1 d . . . . .
C4 C 0.7096(7) 0.5418(7) 0.4910(6) 0.054(2) Uani 1 1 d . . . . .
C5 C 0.5980(8) 0.5780(8) 0.4017(7) 0.068(2) Uani 1 1 d . . . . .
H5A H 0.5503 0.5069 0.3729 0.081 Uiso 1 1 calc R U . . .
H5B H 0.5537 0.6341 0.4243 0.081 Uiso 1 1 calc R U . . .
C6 C 0.6860(9) 0.4513(9) 0.5622(7) 0.082(3) Uani 1 1 d . . . . .
H6A H 0.6228 0.3966 0.5237 0.098 Uiso 1 1 calc R U . . .
H6B H 0.6670 0.4932 0.6132 0.098 Uiso 1 1 calc R U . . .
C7 C 0.8030(9) 0.3815(10) 0.6130(8) 0.088(3) Uani 1 1 d . . . . .
H7A H 0.8514 0.4174 0.6786 0.106 Uiso 1 1 calc R U . . .
H7B H 0.7892 0.2969 0.6235 0.106 Uiso 1 1 calc R U . . .
C8 C 0.8598(8) 0.3927(7) 0.5396(6) 0.058(2) Uani 1 1 d . . . . .
C9 C 0.9624(8) 0.3433(8) 0.5535(6) 0.065(2) Uani 1 1 d . . . . .
H9 H 0.9909 0.3544 0.5032 0.078 Uiso 1 1 calc R U . . .
C10 C 0.8421(9) 0.3939(8) 0.3123(6) 0.071(3) Uani 1 1 d . . . . .
H10A H 0.7901 0.3641 0.2464 0.107 Uiso 1 1 calc R U . . .
H10B H 0.8764 0.3265 0.3572 0.107 Uiso 1 1 calc R U . . .
H10C H 0.9024 0.4415 0.3051 0.107 Uiso 1 1 calc R U . . .
C11 C 0.7714(9) 0.6538(9) 0.5484(8) 0.084(3) Uani 1 1 d . . . . .
H11A H 0.8472 0.6318 0.5982 0.126 Uiso 1 1 calc R U . . .
H11B H 0.7270 0.6896 0.5824 0.126 Uiso 1 1 calc R U . . .
H11C H 0.7794 0.7112 0.5010 0.126 Uiso 1 1 calc R U . . .
C12 C 0.4243(8) 0.6590(8) 0.1582(7) 0.069(3) Uani 1 1 d . . . . .
C13 C 0.3321(10) 0.6296(10) 0.1827(8) 0.084(3) Uani 1 1 d . . . . .
H13 H 0.3338 0.6524 0.2461 0.100 Uiso 1 1 calc R U . . .
C14 C 0.2380(10) 0.5674(11) 0.1151(9) 0.092(3) Uani 1 1 d . . . . .
H14 H 0.1760 0.5493 0.1326 0.111 Uiso 1 1 calc R U . . .
C15 C 0.2340(11) 0.5311(10) 0.0212(9) 0.084(3) Uani 1 1 d . . . . .
C16 C 0.3252(14) 0.5598(12) -0.0018(8) 0.108(5) Uani 1 1 d . . . . .
H16 H 0.3235 0.5359 -0.0649 0.129 Uiso 1 1 calc R U . . .
C17 C 0.4204(11) 0.6228(12) 0.0644(9) 0.098(4) Uani 1 1 d . . . . .
H17 H 0.4818 0.6410 0.0461 0.118 Uiso 1 1 calc R U . . .
C18 C 0.1302(11) 0.4627(10) -0.0541(9) 0.114(4) Uani 1 1 d . . . . .
H18A H 0.1063 0.4020 -0.0184 0.171 Uiso 1 1 calc R U . . .
H18B H 0.1513 0.4244 -0.1046 0.171 Uiso 1 1 calc R U . . .
H18C H 0.0672 0.5183 -0.0872 0.171 Uiso 1 1 calc R U . . .


_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
Br1 C9 1.882(8) . ?
S1 O2 1.413(7) . ?
S1 O1 1.438(7) . ?
S1 N1 1.639(7) . ?
S1 C12 1.761(10) . ?
N1 C1 1.449(10) . ?
N1 C5 1.467(10) . ?
C1 C2 1.509(11) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.327(10) . ?
C2 C10 1.513(11) . ?
C3 C8 1.464(11) . ?
C3 C4 1.510(10) . ?
C4 C11 1.510(11) . ?
C4 C5 1.517(11) . ?
C4 C6 1.536(12) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.551(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.492(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.337(12) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.377(13) . ?
C12 C17 1.378(14) . ?
C13 C14 1.369(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(14) . ?
C14 H14 0.9300 . ?
C15 C16 1.350(16) . ?
C15 C18 1.512(15) . ?
C16 C17 1.375(16) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
O2 S1 O1 120.1(5) . . ?
O2 S1 N1 106.6(4) . . ?
O1 S1 N1 107.1(4) . . ?
O2 S1 C12 108.8(5) . . ?
O1 S1 C12 107.0(5) . . ?
N1 S1 C12 106.5(4) . . ?
C1 N1 C5 113.1(6) . . ?
C1 N1 S1 116.6(5) . . ?
C5 N1 S1 118.8(6) . . ?
N1 C1 C2 112.8(7) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C1 121.2(7) . . ?
C3 C2 C10 125.3(7) . . ?
C1 C2 C10 113.5(7) . . ?
C2 C3 C8 130.7(7) . . ?
C2 C3 C4 122.5(7) . . ?
C8 C3 C4 106.4(7) . . ?
C11 C4 C3 111.3(7) . . ?
C11 C4 C5 109.8(7) . . ?
C3 C4 C5 110.3(7) . . ?
C11 C4 C6 111.5(7) . . ?
C3 C4 C6 102.2(7) . . ?
C5 C4 C6 111.6(7) . . ?
N1 C5 C4 107.5(7) . . ?
N1 C5 H5A 110.2 . . ?
C4 C5 H5A 110.2 . . ?
N1 C5 H5B 110.2 . . ?
C4 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
C4 C6 C7 103.4(8) . . ?
C4 C6 H6A 111.1 . . ?
C7 C6 H6A 111.1 . . ?
C4 C6 H6B 111.1 . . ?
C7 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C6 105.2(7) . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 C3 126.7(8) . . ?
C9 C8 C7 124.6(8) . . ?
C3 C8 C7 108.6(8) . . ?
C8 C9 Br1 122.7(7) . . ?
C8 C9 H9 118.7 . . ?
Br1 C9 H9 118.7 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.5(11) . . ?
C13 C12 S1 118.9(8) . . ?
C17 C12 S1 122.7(9) . . ?
C14 C13 C12 120.8(10) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.7(12) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 117.9(12) . . ?
C16 C15 C18 121.0(12) . . ?
C14 C15 C18 121.1(12) . . ?
C15 C16 C17 122.5(11) . . ?
C15 C16 H16 118.7 . . ?
C17 C16 H16 118.8 . . ?
C16 C17 C12 119.6(11) . . ?
C16 C17 H17 120.2 . . ?
C12 C17 H17 120.2 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 N1 C1 -178.0(7) . . . . ?
O1 S1 N1 C1 -48.3(8) . . . . ?
C12 S1 N1 C1 65.9(7) . . . . ?
O2 S1 N1 C5 41.0(8) . . . . ?
O1 S1 N1 C5 170.7(7) . . . . ?
C12 S1 N1 C5 -75.1(7) . . . . ?
C5 N1 C1 C2 -43.6(10) . . . . ?
S1 N1 C1 C2 173.3(5) . . . . ?
N1 C1 C2 C3 8.4(11) . . . . ?
N1 C1 C2 C10 -174.0(7) . . . . ?
C1 C2 C3 C8 175.2(8) . . . . ?
C10 C2 C3 C8 -2.1(14) . . . . ?
C1 C2 C3 C4 2.5(11) . . . . ?
C10 C2 C3 C4 -174.8(8) . . . . ?
C2 C3 C4 C11 -102.1(9) . . . . ?
C8 C3 C4 C11 83.6(8) . . . . ?
C2 C3 C4 C5 20.0(10) . . . . ?
C8 C3 C4 C5 -154.2(7) . . . . ?
C2 C3 C4 C6 138.8(8) . . . . ?
C8 C3 C4 C6 -35.5(8) . . . . ?
C1 N1 C5 C4 66.3(9) . . . . ?
S1 N1 C5 C4 -151.4(6) . . . . ?
C11 C4 C5 N1 71.3(8) . . . . ?
C3 C4 C5 N1 -51.8(9) . . . . ?
C6 C4 C5 N1 -164.7(7) . . . . ?
C11 C4 C6 C7 -82.7(9) . . . . ?
C3 C4 C6 C7 36.3(9) . . . . ?
C5 C4 C6 C7 154.2(8) . . . . ?
C4 C6 C7 C8 -24.6(10) . . . . ?
C2 C3 C8 C9 28.9(14) . . . . ?
C4 C3 C8 C9 -157.5(8) . . . . ?
C2 C3 C8 C7 -153.1(9) . . . . ?
C4 C3 C8 C7 20.5(9) . . . . ?
C6 C7 C8 C9 -178.9(9) . . . . ?
C6 C7 C8 C3 2.9(10) . . . . ?
C3 C8 C9 Br1 177.2(6) . . . . ?
C7 C8 C9 Br1 -0.6(13) . . . . ?
O2 S1 C12 C13 -28.9(9) . . . . ?
O1 S1 C12 C13 -160.1(8) . . . . ?
N1 S1 C12 C13 85.6(8) . . . . ?
O2 S1 C12 C17 152.4(8) . . . . ?
O1 S1 C12 C17 21.2(9) . . . . ?
N1 S1 C12 C17 -93.1(8) . . . . ?
C17 C12 C13 C14 -0.8(15) . . . . ?
S1 C12 C13 C14 -179.6(8) . . . . ?
C12 C13 C14 C15 0.9(16) . . . . ?
C13 C14 C15 C16 -0.5(16) . . . . ?
C13 C14 C15 C18 -179.8(10) . . . . ?
C14 C15 C16 C17 0.1(17) . . . . ?
C18 C15 C16 C17 179.3(10) . . . . ?
C15 C16 C17 C12 -0.1(17) . . . . ?
C13 C12 C17 C16 0.4(15) . . . . ?
S1 C12 C17 C16 179.1(8) . . . . ?

_refine_diff_density_max         0.851
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.102

_shelxl_version_number           2013-4



