# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_hamm
_database_code_depnum_ccdc_archive 'CCDC 1948156'
loop_
_audit_author_name
_audit_author_address
'Peter Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 N O S'
_chemical_formula_weight         203.25

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   10.9143(2)
_cell_length_b                   7.26579(18)
_cell_length_c                   12.4737(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.425(2)
_cell_angle_gamma                90.00
_cell_volume                     957.99(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11164
_cell_measurement_theta_min      4.1720
_cell_measurement_theta_max      76.0740

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    2.690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.3543
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20246
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.18
_diffrn_reflns_theta_max         75.86
_reflns_number_total             1990
_reflns_number_gt                1791
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0472P)²+0.3528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1990
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.72738(13) 0.0739(2) 0.20909(11) 0.0191(3) Uani 1 1 d . . .
C2 C 0.72333(13) 0.13049(19) 0.31522(12) 0.0186(3) Uani 1 1 d . . .
C3 C 0.46815(13) 0.15354(19) 0.22728(11) 0.0181(3) Uani 1 1 d . . .
C4 C 0.51816(13) 0.1716(2) 0.12572(11) 0.0198(3) Uani 1 1 d . . .
H4A H 0.4485 0.1494 0.0591 0.024 Uiso 1 1 calc R . .
H4B H 0.5493 0.2986 0.1213 0.024 Uiso 1 1 calc R . .
C5 C 0.84289(14) 0.0372(2) 0.18558(12) 0.0239(3) Uani 1 1 d . . .
H5 H 0.8453 -0.0031 0.1137 0.029 Uiso 1 1 calc R . .
C6 C 0.95432(13) 0.0590(2) 0.26655(13) 0.0258(3) Uani 1 1 d . . .
H6 H 1.0330 0.0325 0.2503 0.031 Uiso 1 1 calc R . .
C7 C 0.95158(14) 0.1200(2) 0.37200(13) 0.0243(3) Uani 1 1 d . . .
H7 H 1.0283 0.1375 0.4270 0.029 Uiso 1 1 calc R . .
C8 C 0.83648(14) 0.1548(2) 0.39620(12) 0.0214(3) Uani 1 1 d . . .
H8 H 0.8345 0.1953 0.4681 0.026 Uiso 1 1 calc R . .
C9 C 0.34419(13) 0.14024(19) 0.22494(11) 0.0190(3) Uani 1 1 d . . .
C10 C 0.30901(13) 0.1131(2) 0.32759(12) 0.0201(3) Uani 1 1 d . . .
C11 C 0.23524(14) 0.1504(2) 0.12315(12) 0.0230(3) Uani 1 1 d . . .
H11A H 0.2668 0.1873 0.0594 0.035 Uiso 1 1 calc R . .
H11B H 0.1734 0.2411 0.1350 0.035 Uiso 1 1 calc R . .
H11C H 0.1947 0.0295 0.1090 0.035 Uiso 1 1 calc R . .
N1 N 0.27838(11) 0.08595(19) 0.40787(10) 0.0257(3) Uani 1 1 d . . .
O1 O 0.61914(9) 0.04384(14) 0.12685(8) 0.0207(2) Uani 1 1 d . . .
S1 S 0.58052(3) 0.15677(5) 0.35532(3) 0.01998(13) Uani 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
C1 O1 1.3755(16) . ?
C1 C5 1.3896(19) . ?
C1 C2 1.3973(19) . ?
C2 C8 1.398(2) . ?
C2 S1 1.7620(14) . ?
C3 C9 1.349(2) . ?
C3 C4 1.5049(19) . ?
C3 S1 1.7549(14) . ?
C4 O1 1.4381(17) . ?
C5 C6 1.383(2) . ?
C6 C7 1.395(2) . ?
C7 C8 1.386(2) . ?
C9 C10 1.4390(19) . ?
C9 C11 1.5098(18) . ?
C10 N1 1.1489(19) . ?

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 C1 C5 117.90(12) . . ?
O1 C1 C2 121.96(12) . . ?
C5 C1 C2 120.06(13) . . ?
C1 C2 C8 119.40(13) . . ?
C1 C2 S1 122.67(11) . . ?
C8 C2 S1 117.76(11) . . ?
C9 C3 C4 124.06(13) . . ?
C9 C3 S1 119.36(11) . . ?
C4 C3 S1 116.56(10) . . ?
O1 C4 C3 111.93(11) . . ?
C6 C5 C1 120.19(13) . . ?
C5 C6 C7 120.23(13) . . ?
C8 C7 C6 119.78(14) . . ?
C7 C8 C2 120.31(14) . . ?
C3 C9 C10 118.62(13) . . ?
C3 C9 C11 126.16(13) . . ?
C10 C9 C11 115.22(12) . . ?
N1 C10 C9 177.53(16) . . ?
C1 O1 C4 114.74(10) . . ?
C3 S1 C2 101.96(7) . . ?

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 C1 C2 C8 178.52(13) . . . . ?
C5 C1 C2 C8 1.9(2) . . . . ?
O1 C1 C2 S1 3.3(2) . . . . ?
C5 C1 C2 S1 -173.29(11) . . . . ?
C9 C3 C4 O1 -131.24(14) . . . . ?
S1 C3 C4 O1 50.53(14) . . . . ?
O1 C1 C5 C6 -177.76(13) . . . . ?
C2 C1 C5 C6 -1.0(2) . . . . ?
C1 C5 C6 C7 -0.7(2) . . . . ?
C5 C6 C7 C8 1.4(2) . . . . ?
C6 C7 C8 C2 -0.5(2) . . . . ?
C1 C2 C8 C7 -1.1(2) . . . . ?
S1 C2 C8 C7 174.27(11) . . . . ?
C4 C3 C9 C10 176.50(13) . . . . ?
S1 C3 C9 C10 -5.32(18) . . . . ?
C4 C3 C9 C11 -3.3(2) . . . . ?
S1 C3 C9 C11 174.93(11) . . . . ?
C5 C1 O1 C4 -145.25(13) . . . . ?
C2 C1 O1 C4 38.03(18) . . . . ?
C3 C4 O1 C1 -65.75(15) . . . . ?
C9 C3 S1 C2 169.19(11) . . . . ?
C4 C3 S1 C2 -12.49(12) . . . . ?
C1 C2 S1 C3 -14.24(14) . . . . ?
C8 C2 S1 C3 170.52(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        75.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.048


# end of cif file
####################################################################### 
# 
# 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_seeburg
_database_code_depnum_ccdc_archive 'CCDC 1948158'
loop_
_audit_author_name
_audit_author_address
'Peter Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 N S Se Si'
_chemical_formula_weight         366.45

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'
Si Si 0.0817 0.0704 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   10.6588(4)
_cell_length_b                   8.0663(3)
_cell_length_c                   20.1272(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.886(3)
_cell_angle_gamma                90.00
_cell_volume                     1721.35(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18250
_cell_measurement_theta_min      2.5120
_cell_measurement_theta_max      30.7180

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            88854
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         31.11
_reflns_number_total             5310
_reflns_number_gt                4690
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0285P)²+1.5587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5310
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0718
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.615097(15) 0.79624(2) 0.111414(9) 0.01906(6) Uani 1 1 d . . .
S1 S 0.51838(4) 1.07153(5) 0.20532(2) 0.01745(9) Uani 1 1 d . . .
Si1 Si 0.29183(4) 0.78070(6) 0.03864(2) 0.01610(9) Uani 1 1 d . . .
C1 C 0.48378(15) 0.9312(2) 0.13864(8) 0.0147(3) Uani 1 1 d . . .
C2 C 0.36268(15) 0.9186(2) 0.10980(8) 0.0154(3) Uani 1 1 d . . .
C3 C 0.73783(16) 0.8368(2) 0.18931(9) 0.0200(3) Uani 1 1 d . . .
H3A H 0.7016 0.8017 0.2304 0.024 Uiso 1 1 calc R . .
H3B H 0.8148 0.7703 0.1853 0.024 Uiso 1 1 calc R . .
C4 C 0.77143(15) 1.0161(2) 0.19412(8) 0.0144(3) Uani 1 1 d . . .
C5 C 0.67648(14) 1.1330(2) 0.20020(8) 0.0139(3) Uani 1 1 d . . .
C6 C 0.70378(16) 1.3015(2) 0.20545(8) 0.0167(3) Uani 1 1 d . . .
H6 H 0.6384 1.3797 0.2095 0.020 Uiso 1 1 calc R . .
C7 C 0.82797(16) 1.3540(2) 0.20467(9) 0.0191(3) Uani 1 1 d . . .
H7 H 0.8479 1.4684 0.2095 0.023 Uiso 1 1 calc R . .
C8 C 0.92241(16) 1.2403(2) 0.19689(9) 0.0182(3) Uani 1 1 d . . .
H8 H 1.0067 1.2772 0.1954 0.022 Uiso 1 1 calc R . .
C9 C 0.89461(15) 1.0722(2) 0.19130(8) 0.0169(3) Uani 1 1 d . . .
H9 H 0.9599 0.9950 0.1855 0.020 Uiso 1 1 calc R . .
N1 N 0.19554(14) 1.1066(2) 0.15634(9) 0.0241(3) Uani 1 1 d . . .
C10 C 0.27221(15) 1.0263(2) 0.13598(9) 0.0171(3) Uani 1 1 d . . .
C11 C 0.16111(18) 0.9037(3) -0.00543(10) 0.0287(4) Uani 1 1 d . . .
H11A H 0.1956 1.0032 -0.0248 0.043 Uiso 1 1 calc R . .
H11B H 0.1018 0.9363 0.0264 0.043 Uiso 1 1 calc R . .
H11C H 0.1170 0.8365 -0.0411 0.043 Uiso 1 1 calc R . .
C12 C 0.41008(18) 0.7335(2) -0.02060(9) 0.0222(3) Uani 1 1 d . . .
H12A H 0.3667 0.6940 -0.0629 0.033 Uiso 1 1 calc R . .
H12B H 0.4679 0.6475 -0.0015 0.033 Uiso 1 1 calc R . .
H12C H 0.4579 0.8340 -0.0286 0.033 Uiso 1 1 calc R . .
C13 C 0.23034(17) 0.5846(2) 0.07492(9) 0.0207(3) Uani 1 1 d . . .
C14 C 0.11972(19) 0.6257(3) 0.11603(10) 0.0284(4) Uani 1 1 d . . .
H14A H 0.0881 0.5233 0.1345 0.043 Uiso 1 1 calc R . .
H14B H 0.0519 0.6790 0.0871 0.043 Uiso 1 1 calc R . .
H14C H 0.1490 0.7010 0.1526 0.043 Uiso 1 1 calc R . .
C15 C 0.1847(2) 0.4649(3) 0.01772(10) 0.0315(4) Uani 1 1 d . . .
H15A H 0.2561 0.4336 -0.0067 0.047 Uiso 1 1 calc R . .
H15B H 0.1201 0.5198 -0.0128 0.047 Uiso 1 1 calc R . .
H15C H 0.1488 0.3654 0.0363 0.047 Uiso 1 1 calc R . .
C16 C 0.33608(19) 0.4995(2) 0.12083(10) 0.0258(4) Uani 1 1 d . . .
H16A H 0.3026 0.3996 0.1404 0.039 Uiso 1 1 calc R . .
H16B H 0.3676 0.5759 0.1566 0.039 Uiso 1 1 calc R . .
H16C H 0.4052 0.4689 0.0947 0.039 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C1 1.8977(16) . ?
Se1 C3 1.9636(17) . ?
S1 C1 1.7656(17) . ?
S1 C5 1.7697(16) . ?
Si1 C11 1.8600(19) . ?
Si1 C12 1.8611(18) . ?
Si1 C13 1.8873(18) . ?
Si1 C2 1.9071(17) . ?
C1 C2 1.364(2) . ?
C2 C10 1.437(2) . ?
C3 C4 1.491(2) . ?
C4 C9 1.395(2) . ?
C4 C5 1.398(2) . ?
C5 C6 1.392(2) . ?
C6 C7 1.392(2) . ?
C7 C8 1.383(2) . ?
C8 C9 1.390(2) . ?
N1 C10 1.151(2) . ?
C13 C14 1.544(3) . ?
C13 C16 1.543(3) . ?
C13 C15 1.543(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 C3 97.16(7) . . ?
C1 S1 C5 105.14(8) . . ?
C11 Si1 C12 109.09(9) . . ?
C11 Si1 C13 111.03(9) . . ?
C12 Si1 C13 111.17(9) . . ?
C11 Si1 C2 105.45(9) . . ?
C12 Si1 C2 111.00(8) . . ?
C13 Si1 C2 108.95(7) . . ?
C2 C1 S1 119.08(12) . . ?
C2 C1 Se1 121.90(12) . . ?
S1 C1 Se1 118.98(9) . . ?
C1 C2 C10 116.13(15) . . ?
C1 C2 Si1 130.37(13) . . ?
C10 C2 Si1 113.50(11) . . ?
C4 C3 Se1 110.44(11) . . ?
C9 C4 C5 118.53(15) . . ?
C9 C4 C3 122.20(15) . . ?
C5 C4 C3 119.26(14) . . ?
C6 C5 C4 121.18(14) . . ?
C6 C5 S1 117.52(12) . . ?
C4 C5 S1 121.24(12) . . ?
C7 C6 C5 119.23(15) . . ?
C8 C7 C6 120.24(16) . . ?
C7 C8 C9 120.31(15) . . ?
C8 C9 C4 120.45(15) . . ?
N1 C10 C2 176.74(18) . . ?
C14 C13 C16 109.00(15) . . ?
C14 C13 C15 109.53(15) . . ?
C16 C13 C15 108.87(16) . . ?
C14 C13 Si1 109.99(13) . . ?
C16 C13 Si1 110.08(12) . . ?
C15 C13 Si1 109.35(13) . . ?

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
C5 S1 C1 C2 -150.53(14) . . . . ?
C5 S1 C1 Se1 31.80(11) . . . . ?
C3 Se1 C1 C2 -164.16(14) . . . . ?
C3 Se1 C1 S1 13.43(11) . . . . ?
S1 C1 C2 C10 1.4(2) . . . . ?
Se1 C1 C2 C10 178.97(12) . . . . ?
S1 C1 C2 Si1 -179.19(10) . . . . ?
Se1 C1 C2 Si1 -1.6(2) . . . . ?
C11 Si1 C2 C1 -147.71(17) . . . . ?
C12 Si1 C2 C1 -29.70(19) . . . . ?
C13 Si1 C2 C1 93.05(17) . . . . ?
C11 Si1 C2 C10 31.74(15) . . . . ?
C12 Si1 C2 C10 149.75(12) . . . . ?
C13 Si1 C2 C10 -87.50(14) . . . . ?
C1 Se1 C3 C4 -61.80(13) . . . . ?
Se1 C3 C4 C9 -119.29(15) . . . . ?
Se1 C3 C4 C5 59.28(18) . . . . ?
C9 C4 C5 C6 -2.0(2) . . . . ?
C3 C4 C5 C6 179.40(15) . . . . ?
C9 C4 C5 S1 -179.07(12) . . . . ?
C3 C4 C5 S1 2.3(2) . . . . ?
C1 S1 C5 C6 133.47(13) . . . . ?
C1 S1 C5 C4 -49.33(15) . . . . ?
C4 C5 C6 C7 -0.1(2) . . . . ?
S1 C5 C6 C7 177.15(13) . . . . ?
C5 C6 C7 C8 1.8(3) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C7 C8 C9 C4 -0.6(3) . . . . ?
C5 C4 C9 C8 2.3(2) . . . . ?
C3 C4 C9 C8 -179.10(16) . . . . ?
C11 Si1 C13 C14 -50.54(15) . . . . ?
C12 Si1 C13 C14 -172.19(12) . . . . ?
C2 Si1 C13 C14 65.17(14) . . . . ?
C11 Si1 C13 C16 -170.67(13) . . . . ?
C12 Si1 C13 C16 67.69(14) . . . . ?
C2 Si1 C13 C16 -54.95(14) . . . . ?
C11 Si1 C13 C15 69.78(16) . . . . ?
C12 Si1 C13 C15 -51.87(16) . . . . ?
C2 Si1 C13 C15 -174.51(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.421
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.075


# end of cif file
####################################################################### 
# 
# 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_burgelb
_database_code_depnum_ccdc_archive 'CCDC 1948160'
loop_
_audit_author_name
_audit_author_address
'Peter Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 N S'
_chemical_formula_weight         333.47

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   13.9373(6)
_cell_length_b                   7.7203(3)
_cell_length_c                   17.0136(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.984(5)
_cell_angle_gamma                90.00
_cell_volume                     1759.90(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9491
_cell_measurement_theta_min      2.9070
_cell_measurement_theta_max      29.8650

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95448
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            53738
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         30.03
_reflns_number_total             5123
_reflns_number_gt                4316
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0403P)²+0.8842P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5123
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65904(10) -0.03335(18) 0.66959(9) 0.0211(3) Uani 1 1 d . . .
H1 H 0.6812 -0.1455 0.6596 0.025 Uiso 1 1 calc R . .
C2 C 0.71397(10) 0.06404(19) 0.73523(8) 0.0224(3) Uani 1 1 d . . .
H2 H 0.7738 0.0186 0.7704 0.027 Uiso 1 1 calc R . .
C3 C 0.68123(10) 0.22795(18) 0.74932(8) 0.0202(3) Uani 1 1 d . . .
H3 H 0.7202 0.2947 0.7936 0.024 Uiso 1 1 calc R . .
C4 C 0.59233(9) 0.29698(17) 0.70000(7) 0.0160(2) Uani 1 1 d . . .
C5 C 0.53772(9) 0.19744(17) 0.63383(7) 0.0148(2) Uani 1 1 d . . .
C6 C 0.57183(9) 0.03395(17) 0.61868(8) 0.0173(2) Uani 1 1 d . . .
H6 H 0.5349 -0.0315 0.5731 0.021 Uiso 1 1 calc R . .
C7 C 0.55573(9) 0.47329(17) 0.71526(8) 0.0182(3) Uani 1 1 d . . .
H7A H 0.6119 0.5410 0.7499 0.022 Uiso 1 1 calc R . .
H7B H 0.5044 0.4612 0.7452 0.022 Uiso 1 1 calc R . .
C8 C 0.51120(9) 0.57067(17) 0.63503(7) 0.0169(2) Uani 1 1 d . . .
H8A H 0.4962 0.6912 0.6476 0.020 Uiso 1 1 calc R . .
H8B H 0.5613 0.5752 0.6036 0.020 Uiso 1 1 calc R . .
C9 C 0.41738(9) 0.48776(16) 0.58313(7) 0.0147(2) Uani 1 1 d . . .
C10 C 0.33630(9) 0.58075(16) 0.54378(7) 0.0138(2) Uani 1 1 d . . .
C11 C 0.33785(9) 0.77833(16) 0.53864(8) 0.0161(2) Uani 1 1 d . . .
H11A H 0.3921 0.8180 0.5157 0.019 Uiso 1 1 calc R . .
H11B H 0.3474 0.8309 0.5933 0.019 Uiso 1 1 calc R . .
C12 C 0.23543(9) 0.82645(16) 0.48174(8) 0.0180(2) Uani 1 1 d . . .
H12A H 0.2399 0.9310 0.4492 0.022 Uiso 1 1 calc R . .
H12B H 0.1865 0.8476 0.5132 0.022 Uiso 1 1 calc R . .
C13 C 0.20640(9) 0.66645(16) 0.42640(8) 0.0161(2) Uani 1 1 d . . .
H13A H 0.1334 0.6604 0.4015 0.019 Uiso 1 1 calc R . .
H13B H 0.2407 0.6655 0.3826 0.019 Uiso 1 1 calc R . .
C14 C 0.24250(9) 0.52054(16) 0.48678(7) 0.0136(2) Uani 1 1 d . . .
C15 C 0.18775(9) 0.38038(16) 0.49550(7) 0.0143(2) Uani 1 1 d . . .
C16 C 0.19799(9) 0.27649(16) 0.57313(8) 0.0168(2) Uani 1 1 d . . .
H16A H 0.2411 0.3366 0.6215 0.020 Uiso 1 1 calc R . .
H16B H 0.2253 0.1595 0.5689 0.020 Uiso 1 1 calc R . .
C17 C 0.08902(10) 0.26754(19) 0.57702(9) 0.0236(3) Uani 1 1 d . . .
H17A H 0.0786 0.1657 0.6091 0.028 Uiso 1 1 calc R . .
H17B H 0.0708 0.3736 0.6023 0.028 Uiso 1 1 calc R . .
C18 C 0.02702(10) 0.25175(19) 0.48741(9) 0.0254(3) Uani 1 1 d . . .
H18A H 0.0104 0.1291 0.4727 0.030 Uiso 1 1 calc R . .
H18B H -0.0357 0.3188 0.4776 0.030 Uiso 1 1 calc R . .
C19 C 0.09340(9) 0.32558(16) 0.43826(8) 0.0177(2) Uani 1 1 d . . .
C20 C 0.06961(10) 0.31888(17) 0.35572(8) 0.0200(3) Uani 1 1 d . . .
C21 C -0.02797(12) 0.2506(2) 0.30231(10) 0.0340(4) Uani 1 1 d . . .
H21A H -0.0159 0.1438 0.2754 0.051 Uiso 1 1 calc R . .
H21B H -0.0583 0.3373 0.2608 0.051 Uiso 1 1 calc R . .
H21C H -0.0732 0.2263 0.3360 0.051 Uiso 1 1 calc R . .
C22 C 0.14104(10) 0.36532(17) 0.31238(8) 0.0201(3) Uani 1 1 d . . .
N1 N 0.19409(9) 0.39657(17) 0.27309(7) 0.0261(3) Uani 1 1 d . . .
S1 S 0.42123(2) 0.26171(4) 0.568995(19) 0.01697(8) Uani 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
C1 C6 1.3848(18) . ?
C1 C2 1.388(2) . ?
C2 C3 1.388(2) . ?
C3 C4 1.3966(18) . ?
C4 C5 1.4019(18) . ?
C4 C7 1.5012(18) . ?
C5 C6 1.3975(18) . ?
C5 S1 1.7643(12) . ?
C7 C8 1.5319(18) . ?
C8 C9 1.5045(17) . ?
C9 C10 1.3505(17) . ?
C9 S1 1.7645(13) . ?
C10 C14 1.4723(16) . ?
C10 C11 1.5285(17) . ?
C11 C12 1.5335(18) . ?
C12 C13 1.5382(18) . ?
C13 C14 1.5142(17) . ?
C14 C15 1.3555(17) . ?
C15 C19 1.4668(17) . ?
C15 C16 1.5179(17) . ?
C16 C17 1.5399(18) . ?
C17 C18 1.536(2) . ?
C18 C19 1.5186(18) . ?
C19 C20 1.3521(19) . ?
C20 C22 1.4380(19) . ?
C20 C21 1.5074(19) . ?
C22 N1 1.1506(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.63(13) . . ?
C3 C2 C1 119.86(12) . . ?
C2 C3 C4 121.56(13) . . ?
C3 C4 C5 117.97(12) . . ?
C3 C4 C7 121.98(12) . . ?
C5 C4 C7 120.05(11) . . ?
C6 C5 C4 120.41(12) . . ?
C6 C5 S1 116.09(10) . . ?
C4 C5 S1 123.41(10) . . ?
C1 C6 C5 120.53(12) . . ?
C4 C7 C8 111.37(10) . . ?
C9 C8 C7 112.80(10) . . ?
C10 C9 C8 122.56(11) . . ?
C10 C9 S1 120.72(9) . . ?
C8 C9 S1 116.53(9) . . ?
C9 C10 C14 128.96(11) . . ?
C9 C10 C11 122.40(11) . . ?
C14 C10 C11 107.54(10) . . ?
C10 C11 C12 104.63(10) . . ?
C11 C12 C13 103.54(10) . . ?
C14 C13 C12 101.53(10) . . ?
C15 C14 C10 127.19(11) . . ?
C15 C14 C13 125.19(11) . . ?
C10 C14 C13 106.32(10) . . ?
C14 C15 C19 125.89(11) . . ?
C14 C15 C16 126.60(11) . . ?
C19 C15 C16 106.12(10) . . ?
C15 C16 C17 101.75(10) . . ?
C18 C17 C16 104.64(11) . . ?
C19 C18 C17 104.79(11) . . ?
C20 C19 C15 128.26(12) . . ?
C20 C19 C18 123.04(12) . . ?
C15 C19 C18 108.26(11) . . ?
C19 C20 C22 121.11(12) . . ?
C19 C20 C21 124.19(13) . . ?
C22 C20 C21 114.53(13) . . ?
N1 C22 C20 175.26(14) . . ?
C5 S1 C9 104.49(6) . . ?

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
C6 C1 C2 C3 -0.07(19) . . . . ?
C1 C2 C3 C4 1.59(19) . . . . ?
C2 C3 C4 C5 -1.71(18) . . . . ?
C2 C3 C4 C7 179.34(12) . . . . ?
C3 C4 C5 C6 0.34(17) . . . . ?
C7 C4 C5 C6 179.31(11) . . . . ?
C3 C4 C5 S1 176.79(9) . . . . ?
C7 C4 C5 S1 -4.23(16) . . . . ?
C2 C1 C6 C5 -1.28(19) . . . . ?
C4 C5 C6 C1 1.15(18) . . . . ?
S1 C5 C6 C1 -175.56(10) . . . . ?
C3 C4 C7 C8 139.90(12) . . . . ?
C5 C4 C7 C8 -39.03(15) . . . . ?
C4 C7 C8 C9 66.18(13) . . . . ?
C7 C8 C9 C10 137.44(12) . . . . ?
C7 C8 C9 S1 -47.51(13) . . . . ?
C8 C9 C10 C14 175.33(11) . . . . ?
S1 C9 C10 C14 0.49(18) . . . . ?
C8 C9 C10 C11 8.89(18) . . . . ?
S1 C9 C10 C11 -165.95(9) . . . . ?
C9 C10 C11 C12 174.16(11) . . . . ?
C14 C10 C11 C12 5.18(13) . . . . ?
C10 C11 C12 C13 -27.95(12) . . . . ?
C11 C12 C13 C14 39.70(11) . . . . ?
C9 C10 C14 C15 44.8(2) . . . . ?
C11 C10 C14 C15 -147.14(12) . . . . ?
C9 C10 C14 C13 -147.79(12) . . . . ?
C11 C10 C14 C13 20.22(12) . . . . ?
C12 C13 C14 C15 130.49(12) . . . . ?
C12 C13 C14 C10 -37.20(12) . . . . ?
C10 C14 C15 C19 178.74(12) . . . . ?
C13 C14 C15 C19 13.6(2) . . . . ?
C10 C14 C15 C16 14.1(2) . . . . ?
C13 C14 C15 C16 -151.00(12) . . . . ?
C14 C15 C16 C17 130.52(13) . . . . ?
C19 C15 C16 C17 -36.57(13) . . . . ?
C15 C16 C17 C18 36.10(13) . . . . ?
C16 C17 C18 C19 -22.76(14) . . . . ?
C14 C15 C19 C20 43.5(2) . . . . ?
C16 C15 C19 C20 -149.35(13) . . . . ?
C14 C15 C19 C18 -144.06(13) . . . . ?
C16 C15 C19 C18 23.15(14) . . . . ?
C17 C18 C19 C20 173.05(13) . . . . ?
C17 C18 C19 C15 0.08(14) . . . . ?
C15 C19 C20 C22 1.4(2) . . . . ?
C18 C19 C20 C22 -170.10(12) . . . . ?
C15 C19 C20 C21 176.33(13) . . . . ?
C18 C19 C20 C21 4.8(2) . . . . ?
C6 C5 S1 C9 -163.35(9) . . . . ?
C4 C5 S1 C9 20.06(12) . . . . ?
C10 C9 S1 C5 -178.29(10) . . . . ?
C8 C9 S1 C5 6.56(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.054


# end of cif file
####################################################################### 
# 
# 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_tschiis
_database_code_depnum_ccdc_archive 'CCDC 1948162'
loop_
_audit_author_name
_audit_author_address
'Peter Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 S'
_chemical_formula_weight         304.43

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_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                   7.5133(2)
_cell_length_b                   25.6215(7)
_cell_length_c                   8.2645(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.591(3)
_cell_angle_gamma                90.00
_cell_volume                     1563.84(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    102(2)
_cell_measurement_reflns_used    23724
_cell_measurement_theta_min      2.6370
_cell_measurement_theta_max      30.7530

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95543
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      102(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            82578
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         31.04
_reflns_number_total             4812
_reflns_number_gt                4324
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0374P)²+0.8754P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4812
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.70492(3) 0.179624(10) 0.58117(3) 0.01345(7) Uani 1 1 d . . .
C1 C 0.87759(15) 0.06140(5) 0.32921(14) 0.0180(2) Uani 1 1 d . . .
H1 H 0.9464 0.0575 0.2444 0.022 Uiso 1 1 calc R . .
C2 C 0.81177(15) 0.01755(4) 0.39840(15) 0.0181(2) Uani 1 1 d . . .
H2 H 0.8344 -0.0163 0.3597 0.022 Uiso 1 1 calc R . .
C3 C 0.71289(15) 0.02317(4) 0.52405(14) 0.0158(2) Uani 1 1 d . . .
H3 H 0.6699 -0.0070 0.5713 0.019 Uiso 1 1 calc R . .
C4 C 0.67584(14) 0.07238(4) 0.58176(13) 0.01319(19) Uani 1 1 d . . .
C5 C 0.74078(14) 0.11627(4) 0.50964(13) 0.01287(19) Uani 1 1 d . . .
C6 C 0.84221(15) 0.11086(4) 0.38477(14) 0.0157(2) Uani 1 1 d . . .
H6 H 0.8868 0.1409 0.3380 0.019 Uiso 1 1 calc R . .
C7 C 0.56460(15) 0.08056(4) 0.71334(13) 0.0148(2) Uani 1 1 d . . .
H7A H 0.6439 0.0928 0.8154 0.018 Uiso 1 1 calc R . .
H7B H 0.5098 0.0470 0.7377 0.018 Uiso 1 1 calc R . .
C8 C 0.41479(15) 0.12071(4) 0.65862(14) 0.0158(2) Uani 1 1 d . . .
H8A H 0.3353 0.1077 0.5577 0.019 Uiso 1 1 calc R . .
H8B H 0.3403 0.1237 0.7454 0.019 Uiso 1 1 calc R . .
C9 C 0.48301(14) 0.17450(4) 0.62446(13) 0.01286(19) Uani 1 1 d . . .
C10 C 0.37761(14) 0.21715(4) 0.62570(13) 0.01313(19) Uani 1 1 d . . .
C11 C 0.17973(15) 0.21256(4) 0.64224(15) 0.0183(2) Uani 1 1 d . . .
H11A H 0.1690 0.1973 0.7501 0.022 Uiso 1 1 calc R . .
H11B H 0.1123 0.1903 0.5538 0.022 Uiso 1 1 calc R . .
C12 C 0.10684(15) 0.26859(4) 0.62739(15) 0.0179(2) Uani 1 1 d . . .
H12A H 0.1076 0.2838 0.7376 0.021 Uiso 1 1 calc R . .
H12B H -0.0185 0.2694 0.5640 0.021 Uiso 1 1 calc R . .
C13 C 0.23568(14) 0.29865(4) 0.53668(14) 0.0151(2) Uani 1 1 d . . .
H13A H 0.1965 0.2959 0.4159 0.018 Uiso 1 1 calc R . .
H13B H 0.2418 0.3360 0.5682 0.018 Uiso 1 1 calc R . .
C14 C 0.41653(14) 0.27203(4) 0.59255(13) 0.01289(19) Uani 1 1 d . . .
C15 C 0.58277(14) 0.29440(4) 0.62189(13) 0.01353(19) Uani 1 1 d . . .
H15 H 0.6799 0.2725 0.6708 0.016 Uiso 1 1 calc R . .
C16 C 0.63152(14) 0.34821(4) 0.58751(13) 0.01295(19) Uani 1 1 d . . .
C17 C 0.53163(15) 0.37893(4) 0.46190(13) 0.0148(2) Uani 1 1 d . . .
H17 H 0.4265 0.3648 0.3946 0.018 Uiso 1 1 calc R . .
C18 C 0.58459(15) 0.42968(4) 0.43485(14) 0.0176(2) Uani 1 1 d . . .
H18 H 0.5135 0.4502 0.3513 0.021 Uiso 1 1 calc R . .
C19 C 0.74096(16) 0.45075(4) 0.52904(15) 0.0190(2) Uani 1 1 d . . .
H19 H 0.7763 0.4855 0.5105 0.023 Uiso 1 1 calc R . .
C20 C 0.84502(16) 0.42028(4) 0.65077(15) 0.0184(2) Uani 1 1 d . . .
H20 H 0.9534 0.4340 0.7138 0.022 Uiso 1 1 calc R . .
C21 C 0.79034(15) 0.36985(4) 0.68001(14) 0.0157(2) Uani 1 1 d . . .
H21 H 0.8616 0.3496 0.7641 0.019 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C5 1.7652(11) . ?
S1 C9 1.7731(11) . ?
C1 C6 1.3902(15) . ?
C1 C2 1.3919(16) . ?
C2 C3 1.3910(16) . ?
C3 C4 1.3942(15) . ?
C4 C5 1.4015(14) . ?
C4 C7 1.5030(15) . ?
C5 C6 1.3979(15) . ?
C7 C8 1.5305(15) . ?
C8 C9 1.5149(14) . ?
C9 C10 1.3506(14) . ?
C10 C14 1.4721(14) . ?
C10 C11 1.5224(15) . ?
C11 C12 1.5333(16) . ?
C12 C13 1.5360(15) . ?
C13 C14 1.5147(14) . ?
C14 C15 1.3551(14) . ?
C15 C16 1.4675(14) . ?
C16 C17 1.4050(15) . ?
C16 C21 1.4073(15) . ?
C17 C18 1.3900(15) . ?
C18 C19 1.3934(16) . ?
C19 C20 1.3941(17) . ?
C20 C21 1.3904(15) . ?

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
C5 S1 C9 101.92(5) . . ?
C6 C1 C2 119.75(10) . . ?
C3 C2 C1 120.14(10) . . ?
C2 C3 C4 121.10(10) . . ?
C3 C4 C5 118.24(10) . . ?
C3 C4 C7 123.10(9) . . ?
C5 C4 C7 118.63(9) . . ?
C6 C5 C4 120.94(10) . . ?
C6 C5 S1 118.41(8) . . ?
C4 C5 S1 120.59(8) . . ?
C1 C6 C5 119.83(10) . . ?
C4 C7 C8 110.88(9) . . ?
C9 C8 C7 114.26(9) . . ?
C10 C9 C8 121.04(9) . . ?
C10 C9 S1 121.07(8) . . ?
C8 C9 S1 117.90(7) . . ?
C9 C10 C14 129.39(10) . . ?
C9 C10 C11 121.46(9) . . ?
C14 C10 C11 108.73(9) . . ?
C10 C11 C12 105.12(9) . . ?
C11 C12 C13 105.11(9) . . ?
C14 C13 C12 103.64(9) . . ?
C15 C14 C10 125.38(10) . . ?
C15 C14 C13 127.56(10) . . ?
C10 C14 C13 106.81(9) . . ?
C14 C15 C16 128.14(10) . . ?
C17 C16 C21 117.72(10) . . ?
C17 C16 C15 123.42(9) . . ?
C21 C16 C15 118.81(10) . . ?
C18 C17 C16 120.87(10) . . ?
C17 C18 C19 120.63(10) . . ?
C18 C19 C20 119.32(10) . . ?
C21 C20 C19 120.09(10) . . ?
C20 C21 C16 121.32(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.80(17) . . . . ?
C1 C2 C3 C4 0.78(17) . . . . ?
C2 C3 C4 C5 0.07(16) . . . . ?
C2 C3 C4 C7 177.96(10) . . . . ?
C3 C4 C5 C6 -0.89(15) . . . . ?
C7 C4 C5 C6 -178.88(10) . . . . ?
C3 C4 C5 S1 -177.99(8) . . . . ?
C7 C4 C5 S1 4.02(14) . . . . ?
C9 S1 C5 C6 144.86(9) . . . . ?
C9 S1 C5 C4 -37.97(10) . . . . ?
C2 C1 C6 C5 -0.02(17) . . . . ?
C4 C5 C6 C1 0.88(16) . . . . ?
S1 C5 C6 C1 178.04(8) . . . . ?
C3 C4 C7 C8 -129.17(11) . . . . ?
C5 C4 C7 C8 48.71(13) . . . . ?
C4 C7 C8 C9 -61.48(12) . . . . ?
C7 C8 C9 C10 -159.16(10) . . . . ?
C7 C8 C9 S1 21.34(12) . . . . ?
C5 S1 C9 C10 -156.02(9) . . . . ?
C5 S1 C9 C8 23.48(9) . . . . ?
C8 C9 C10 C14 -178.56(10) . . . . ?
S1 C9 C10 C14 0.93(16) . . . . ?
C8 C9 C10 C11 -6.93(16) . . . . ?
S1 C9 C10 C11 172.55(8) . . . . ?
C9 C10 C11 C12 -176.53(10) . . . . ?
C14 C10 C11 C12 -3.36(12) . . . . ?
C10 C11 C12 C13 22.01(12) . . . . ?
C11 C12 C13 C14 -32.10(11) . . . . ?
C9 C10 C14 C15 -29.93(18) . . . . ?
C11 C10 C14 C15 157.60(11) . . . . ?
C9 C10 C14 C13 155.44(11) . . . . ?
C11 C10 C14 C13 -17.02(11) . . . . ?
C12 C13 C14 C15 -144.10(11) . . . . ?
C12 C13 C14 C10 30.37(11) . . . . ?
C10 C14 C15 C16 178.07(10) . . . . ?
C13 C14 C15 C16 -8.43(18) . . . . ?
C14 C15 C16 C17 -27.00(17) . . . . ?
C14 C15 C16 C21 155.67(11) . . . . ?
C21 C16 C17 C18 -2.52(15) . . . . ?
C15 C16 C17 C18 -179.88(10) . . . . ?
C16 C17 C18 C19 1.74(17) . . . . ?
C17 C18 C19 C20 0.33(17) . . . . ?
C18 C19 C20 C21 -1.54(17) . . . . ?
C19 C20 C21 C16 0.71(17) . . . . ?
C17 C16 C21 C20 1.31(16) . . . . ?
C15 C16 C21 C20 178.79(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.053


# end of cif file
####################################################################### 
# 
# 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_thiete
_database_code_depnum_ccdc_archive 'CCDC 1948161'
loop_
_audit_author_name
_audit_author_address
'Peter Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 N S'
_chemical_formula_weight         173.23

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   6.9027(6)
_cell_length_b                   7.3743(6)
_cell_length_c                   9.3503(7)
_cell_angle_alpha                68.861(8)
_cell_angle_beta                 73.292(8)
_cell_angle_gamma                84.246(6)
_cell_volume                     425.18(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7083
_cell_measurement_theta_min      3.0660
_cell_measurement_theta_max      29.8490

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             180
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22785
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         30.97
_reflns_number_total             2532
_reflns_number_gt                2286
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0351P)²+0.1941P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2532
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0813
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6813(2) 0.27485(17) 0.11670(14) 0.0235(3) Uani 1 1 d . . .
H1 H 0.7089 0.2884 0.0078 0.028 Uiso 1 1 calc R . .
C2 C 0.83488(19) 0.21287(17) 0.19396(14) 0.0217(2) Uani 1 1 d . . .
H2 H 0.9655 0.1862 0.1364 0.026 Uiso 1 1 calc R . .
C3 C 0.79934(17) 0.18986(16) 0.35292(13) 0.0177(2) Uani 1 1 d . . .
H3 H 0.9041 0.1473 0.4047 0.021 Uiso 1 1 calc R . .
C4 C 0.60643(16) 0.23031(15) 0.43604(12) 0.0147(2) Uani 1 1 d . . .
C5 C 0.45395(17) 0.29421(15) 0.35718(13) 0.0165(2) Uani 1 1 d . . .
C6 C 0.4899(2) 0.31668(16) 0.19669(13) 0.0210(2) Uani 1 1 d . . .
H6 H 0.3860 0.3594 0.1440 0.025 Uiso 1 1 calc R . .
C7 C 0.53091(17) 0.21426(15) 0.60136(12) 0.0152(2) Uani 1 1 d . . .
C8 C 0.33189(17) 0.26385(15) 0.64455(13) 0.0164(2) Uani 1 1 d . . .
C9 C 0.65256(17) 0.15056(16) 0.71072(13) 0.0183(2) Uani 1 1 d . . .
C10 C 0.20834(18) 0.26248(17) 0.80485(14) 0.0211(2) Uani 1 1 d . . .
H10A H 0.2792 0.1887 0.8850 0.032 Uiso 1 1 calc R . .
H10B H 0.0769 0.2016 0.8309 0.032 Uiso 1 1 calc R . .
H10C H 0.1879 0.3963 0.8039 0.032 Uiso 1 1 calc R . .
N1 N 0.75174(17) 0.09893(17) 0.79757(13) 0.0258(2) Uani 1 1 d . . .
S1 S 0.22770(4) 0.33266(4) 0.48490(3) 0.01811(9) Uani 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
C1 C6 1.3845(18) . ?
C1 C2 1.3997(18) . ?
C2 C3 1.3837(16) . ?
C3 C4 1.3996(15) . ?
C4 C5 1.4035(16) . ?
C4 C7 1.4465(14) . ?
C5 C6 1.3985(15) . ?
C5 S1 1.7403(12) . ?
C7 C8 1.3678(15) . ?
C7 C9 1.4281(15) . ?
C8 C10 1.4933(15) . ?
C8 S1 1.7323(12) . ?
C9 N1 1.1478(16) . ?

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
C6 C1 C2 120.97(11) . . ?
C3 C2 C1 120.99(11) . . ?
C2 C3 C4 118.87(11) . . ?
C3 C4 C5 119.74(10) . . ?
C3 C4 C7 129.41(10) . . ?
C5 C4 C7 110.84(10) . . ?
C6 C5 C4 121.31(11) . . ?
C6 C5 S1 127.30(9) . . ?
C4 C5 S1 111.38(8) . . ?
C1 C6 C5 118.11(11) . . ?
C8 C7 C9 122.76(10) . . ?
C8 C7 C4 114.16(10) . . ?
C9 C7 C4 123.08(10) . . ?
C7 C8 C10 127.68(11) . . ?
C7 C8 S1 111.22(8) . . ?
C10 C8 S1 121.10(9) . . ?
N1 C9 C7 179.36(13) . . ?
C8 S1 C5 92.40(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
C6 C1 C2 C3 0.61(18) . . . . ?
C1 C2 C3 C4 -0.21(17) . . . . ?
C2 C3 C4 C5 -0.41(16) . . . . ?
C2 C3 C4 C7 178.67(11) . . . . ?
C3 C4 C5 C6 0.66(16) . . . . ?
C7 C4 C5 C6 -178.58(10) . . . . ?
C3 C4 C5 S1 179.43(8) . . . . ?
C7 C4 C5 S1 0.19(11) . . . . ?
C2 C1 C6 C5 -0.36(17) . . . . ?
C4 C5 C6 C1 -0.28(17) . . . . ?
S1 C5 C6 C1 -178.83(9) . . . . ?
C3 C4 C7 C8 -179.24(11) . . . . ?
C5 C4 C7 C8 -0.09(13) . . . . ?
C3 C4 C7 C9 0.22(18) . . . . ?
C5 C4 C7 C9 179.37(10) . . . . ?
C9 C7 C8 C10 0.23(18) . . . . ?
C4 C7 C8 C10 179.70(10) . . . . ?
C9 C7 C8 S1 -179.51(8) . . . . ?
C4 C7 C8 S1 -0.05(12) . . . . ?
C7 C8 S1 C5 0.13(9) . . . . ?
C10 C8 S1 C5 -179.63(9) . . . . ?
C6 C5 S1 C8 178.49(11) . . . . ?
C4 C5 S1 C8 -0.18(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.938
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.055


# end of cif file
####################################################################### 
# 
# 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_veji
_database_code_depnum_ccdc_archive 'CCDC 1948157'
loop_
_audit_author_name
_audit_author_address
'Peter Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 N O S'
_chemical_formula_weight         265.32

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   12.2557(2)
_cell_length_b                   9.5626(2)
_cell_length_c                   21.5616(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2526.94(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    24382
_cell_measurement_theta_min      5.4530
_cell_measurement_theta_max      76.0140

_exptl_crystal_description       'irregular tablet'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    2.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.3543
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49411
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.10
_diffrn_reflns_theta_max         76.08
_reflns_number_total             2638
_reflns_number_gt                2422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0442P)²+0.8618P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2638
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.55543(10) 0.78760(12) 0.47008(6) 0.0227(2) Uani 1 1 d . . .
C2 C 0.66336(10) 0.77214(13) 0.45087(5) 0.0236(3) Uani 1 1 d . . .
C3 C 0.60486(9) 0.59254(12) 0.55732(5) 0.0223(2) Uani 1 1 d . . .
C4 C 0.68682(10) 0.56526(13) 0.50714(6) 0.0240(3) Uani 1 1 d . . .
H4A H 0.7448 0.5035 0.5237 0.029 Uiso 1 1 calc R . .
H4B H 0.6505 0.5153 0.4726 0.029 Uiso 1 1 calc R . .
C5 C 0.70049(10) 0.84300(14) 0.39850(6) 0.0280(3) Uani 1 1 d . . .
H5 H 0.7740 0.8326 0.3852 0.034 Uiso 1 1 calc R . .
C6 C 0.62949(11) 0.92890(14) 0.36586(6) 0.0303(3) Uani 1 1 d . . .
H6 H 0.6551 0.9791 0.3308 0.036 Uiso 1 1 calc R . .
C7 C 0.52118(11) 0.94206(14) 0.38410(6) 0.0289(3) Uani 1 1 d . . .
H7 H 0.4727 0.9995 0.3610 0.035 Uiso 1 1 calc R . .
C8 C 0.48415(10) 0.87129(14) 0.43596(6) 0.0267(3) Uani 1 1 d . . .
H8 H 0.4101 0.8797 0.4483 0.032 Uiso 1 1 calc R . .
C9 C 0.59959(9) 0.52087(13) 0.61115(5) 0.0228(2) Uani 1 1 d . . .
C10 C 0.51336(9) 0.54300(13) 0.65926(6) 0.0220(2) Uani 1 1 d . . .
C11 C 0.49891(10) 0.67446(14) 0.68644(6) 0.0248(3) Uani 1 1 d . . .
H11 H 0.5453 0.7500 0.6753 0.030 Uiso 1 1 calc R . .
C12 C 0.41648(10) 0.69430(14) 0.72979(6) 0.0269(3) Uani 1 1 d . . .
H12 H 0.4057 0.7841 0.7476 0.032 Uiso 1 1 calc R . .
C13 C 0.34964(10) 0.58382(14) 0.74733(6) 0.0273(3) Uani 1 1 d . . .
H13 H 0.2935 0.5981 0.7770 0.033 Uiso 1 1 calc R . .
C14 C 0.36523(10) 0.45249(13) 0.72130(6) 0.0270(3) Uani 1 1 d . . .
H14 H 0.3203 0.3765 0.7337 0.032 Uiso 1 1 calc R . .
C15 C 0.44650(10) 0.43205(13) 0.67717(6) 0.0245(3) Uani 1 1 d . . .
H15 H 0.4565 0.3423 0.6592 0.029 Uiso 1 1 calc R . .
C16 C 0.67947(10) 0.41453(13) 0.62431(6) 0.0263(3) Uani 1 1 d . . .
N1 N 0.74268(10) 0.33090(13) 0.63736(5) 0.0351(3) Uani 1 1 d . . .
O1 O 0.73579(7) 0.69033(10) 0.48355(4) 0.0265(2) Uani 1 1 d . . .
S1 S 0.50650(2) 0.71849(3) 0.540704(13) 0.02414(11) Uani 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
C1 C2 1.3939(17) . ?
C1 C8 1.3946(18) . ?
C1 S1 1.7650(12) . ?
C2 O1 1.3771(15) . ?
C2 C5 1.3933(17) . ?
C3 C9 1.3495(17) . ?
C3 C4 1.4992(16) . ?
C3 S1 1.7413(12) . ?
C4 O1 1.4315(15) . ?
C5 C6 1.3883(19) . ?
C6 C7 1.3902(19) . ?
C7 C8 1.3835(18) . ?
C9 C16 1.4397(17) . ?
C9 C10 1.4960(16) . ?
C10 C15 1.3951(17) . ?
C10 C11 1.3982(18) . ?
C11 C12 1.3893(17) . ?
C12 C13 1.3894(18) . ?
C13 C14 1.3888(18) . ?
C14 C15 1.3913(18) . ?
C16 N1 1.1484(17) . ?

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
C2 C1 C8 119.90(11) . . ?
C2 C1 S1 122.62(10) . . ?
C8 C1 S1 117.21(9) . . ?
O1 C2 C5 118.70(11) . . ?
O1 C2 C1 121.33(11) . . ?
C5 C2 C1 119.95(12) . . ?
C9 C3 C4 124.36(11) . . ?
C9 C3 S1 119.68(9) . . ?
C4 C3 S1 115.83(9) . . ?
O1 C4 C3 113.08(10) . . ?
C6 C5 C2 119.60(12) . . ?
C5 C6 C7 120.57(12) . . ?
C8 C7 C6 119.84(12) . . ?
C7 C8 C1 120.10(12) . . ?
C3 C9 C16 119.71(11) . . ?
C3 C9 C10 123.94(11) . . ?
C16 C9 C10 116.34(11) . . ?
C15 C10 C11 119.56(11) . . ?
C15 C10 C9 119.95(11) . . ?
C11 C10 C9 120.48(11) . . ?
C12 C11 C10 119.79(12) . . ?
C11 C12 C13 120.53(12) . . ?
C14 C13 C12 119.77(12) . . ?
C13 C14 C15 120.13(12) . . ?
C14 C15 C10 120.20(12) . . ?
N1 C16 C9 177.18(13) . . ?
C2 O1 C4 112.71(9) . . ?
C3 S1 C1 101.61(6) . . ?

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
C8 C1 C2 O1 179.96(11) . . . . ?
S1 C1 C2 O1 6.14(17) . . . . ?
C8 C1 C2 C5 1.55(18) . . . . ?
S1 C1 C2 C5 -172.27(9) . . . . ?
C9 C3 C4 O1 -134.12(12) . . . . ?
S1 C3 C4 O1 50.07(12) . . . . ?
O1 C2 C5 C6 -178.32(11) . . . . ?
C1 C2 C5 C6 0.13(18) . . . . ?
C2 C5 C6 C7 -1.58(19) . . . . ?
C5 C6 C7 C8 1.3(2) . . . . ?
C6 C7 C8 C1 0.38(19) . . . . ?
C2 C1 C8 C7 -1.81(19) . . . . ?
S1 C1 C8 C7 172.34(10) . . . . ?
C4 C3 C9 C16 2.97(18) . . . . ?
S1 C3 C9 C16 178.62(9) . . . . ?
C4 C3 C9 C10 -176.12(11) . . . . ?
S1 C3 C9 C10 -0.47(16) . . . . ?
C3 C9 C10 C15 121.32(13) . . . . ?
C16 C9 C10 C15 -57.80(15) . . . . ?
C3 C9 C10 C11 -58.52(17) . . . . ?
C16 C9 C10 C11 122.36(13) . . . . ?
C15 C10 C11 C12 -1.65(18) . . . . ?
C9 C10 C11 C12 178.20(11) . . . . ?
C10 C11 C12 C13 1.35(19) . . . . ?
C11 C12 C13 C14 -0.07(19) . . . . ?
C12 C13 C14 C15 -0.89(19) . . . . ?
C13 C14 C15 C10 0.58(18) . . . . ?
C11 C10 C15 C14 0.69(18) . . . . ?
C9 C10 C15 C14 -179.16(11) . . . . ?
C5 C2 O1 C4 -142.95(11) . . . . ?
C1 C2 O1 C4 38.62(15) . . . . ?
C3 C4 O1 C2 -68.36(13) . . . . ?
C9 C3 S1 C1 175.87(10) . . . . ?
C4 C3 S1 C1 -8.12(10) . . . . ?
C2 C1 S1 C3 -19.52(12) . . . . ?
C8 C1 S1 C3 166.50(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        75.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.044


# end of cif file
####################################################################### 
# 
# 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_bulrush
_database_code_depnum_ccdc_archive 'CCDC 1948159'
loop_
_audit_author_name
_audit_author_address
'Peter Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N S'
_chemical_formula_weight         267.38

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   11.1885(7)
_cell_length_b                   11.2630(4)
_cell_length_c                   12.1884(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.756(8)
_cell_angle_gamma                90.00
_cell_volume                     1371.50(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6960
_cell_measurement_theta_min      2.5940
_cell_measurement_theta_max      28.4130

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96983
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31457
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         29.12
_reflns_number_total             3577
_reflns_number_gt                3013
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

 The atom C12 is disordered over two positions with relative occupancy
 ca. 80:20. Appropriate restraints were used to improve refinement
 stability, but the dimensions of disordered groups should be interpreted
 with caution.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0356P)²+0.7938P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3577
_refine_ls_number_parameters     178
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44407(3) 0.16565(3) 0.59947(3) 0.01456(10) Uani 1 1 d . . .
N1 N 0.14783(13) 0.05938(11) 0.45647(12) 0.0226(3) Uani 1 1 d . . .
C1 C 0.84693(14) 0.13950(12) 0.76017(13) 0.0179(3) Uani 1 1 d . . .
H1 H 0.9129 0.0994 0.7453 0.022 Uiso 1 1 calc R . .
C2 C 0.88510(14) 0.21155(13) 0.86329(13) 0.0194(3) Uani 1 1 d . . .
H2 H 0.9773 0.2218 0.9179 0.023 Uiso 1 1 calc R . .
C3 C 0.78896(14) 0.26826(12) 0.88646(13) 0.0187(3) Uani 1 1 d . . .
H3 H 0.8158 0.3179 0.9566 0.022 Uiso 1 1 calc R . .
C4 C 0.65322(14) 0.25331(12) 0.80800(12) 0.0162(3) Uani 1 1 d . . .
C5 C 0.61640(13) 0.18377(11) 0.70261(12) 0.0140(3) Uani 1 1 d . . .
C6 C 0.71211(14) 0.12625(12) 0.67891(12) 0.0155(3) Uani 1 1 d . . .
H6 H 0.6857 0.0782 0.6077 0.019 Uiso 1 1 calc R . .
C7 C 0.54412(15) 0.30705(14) 0.83095(13) 0.0217(3) Uani 1 1 d . . .
H7A H 0.5842 0.3591 0.9041 0.026 Uiso 1 1 calc R . .
H7B H 0.4942 0.2432 0.8483 0.026 Uiso 1 1 calc R . .
C8 C 0.44750(15) 0.37922(13) 0.72078(13) 0.0210(3) Uani 1 1 d . . .
H8A H 0.3735 0.4074 0.7375 0.025 Uiso 1 1 calc R . .
H8B H 0.4953 0.4501 0.7127 0.025 Uiso 1 1 calc R . .
C9 C 0.38784(14) 0.31323(12) 0.59916(13) 0.0158(3) Uani 1 1 d . . .
C10 C 0.29828(14) 0.36705(12) 0.49596(13) 0.0169(3) Uani 1 1 d . A .
C11 C 0.26343(17) 0.49785(13) 0.49210(14) 0.0266(3) Uani 1 1 d D . .
H11A H 0.1723 0.5089 0.4846 0.032 Uiso 0.814(8) 1 calc PR A 1
H11B H 0.3286 0.5401 0.5662 0.032 Uiso 0.814(8) 1 calc PR A 1
H11C H 0.3453 0.5451 0.5398 0.032 Uiso 0.186(8) 1 calc PR A 2
H11D H 0.2007 0.5102 0.5280 0.032 Uiso 0.186(8) 1 calc PR A 2
C12 C 0.2718(3) 0.53940(16) 0.3786(2) 0.0268(7) Uani 0.814(8) 1 d PD A 1
H12A H 0.3652 0.5601 0.3979 0.032 Uiso 0.814(8) 1 calc PR A 1
H12B H 0.2147 0.6102 0.3436 0.032 Uiso 0.814(8) 1 calc PR A 1
C13 C 0.22209(16) 0.43497(13) 0.28727(14) 0.0225(3) Uani 1 1 d D . .
H13A H 0.1279 0.4471 0.2257 0.027 Uiso 0.814(8) 1 calc PR A 1
H13B H 0.2781 0.4256 0.2440 0.027 Uiso 0.814(8) 1 calc PR A 1
H13C H 0.3050 0.4477 0.2787 0.027 Uiso 0.186(8) 1 calc PR A 2
H13D H 0.1458 0.4261 0.2046 0.027 Uiso 0.186(8) 1 calc PR A 2
C12' C 0.1985(13) 0.5360(7) 0.3574(8) 0.023(3) Uiso 0.186(8) 1 d PD A 2
H12C H 0.1014 0.5497 0.3276 0.028 Uiso 0.186(8) 1 calc PR A 2
H12D H 0.2399 0.6101 0.3470 0.028 Uiso 0.186(8) 1 calc PR A 2
C14 C 0.23483(13) 0.32735(12) 0.36712(12) 0.0160(3) Uani 1 1 d . A .
C15 C 0.17853(14) 0.22158(12) 0.32112(12) 0.0165(3) Uani 1 1 d . . .
C16 C 0.10781(15) 0.19452(14) 0.18502(13) 0.0237(3) Uani 1 1 d . A .
H16A H 0.0110 0.2030 0.1551 0.035 Uiso 1 1 calc R . .
H16B H 0.1283 0.1130 0.1709 0.035 Uiso 1 1 calc R . .
H16C H 0.1383 0.2500 0.1409 0.035 Uiso 1 1 calc R . .
C17 C 0.16588(13) 0.13189(12) 0.39917(12) 0.0166(3) Uani 1 1 d . A .


_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 C9 1.7767(14) . ?
S1 C5 1.7768(14) . ?
N1 C17 1.1500(19) . ?
C1 C6 1.3905(19) . ?
C1 C2 1.392(2) . ?
C2 C3 1.385(2) . ?
C3 C4 1.3934(19) . ?
C4 C5 1.3988(19) . ?
C4 C7 1.497(2) . ?
C5 C6 1.3887(19) . ?
C7 C8 1.525(2) . ?
C8 C9 1.5181(19) . ?
C9 C10 1.3487(19) . ?
C10 C14 1.4717(19) . ?
C10 C11 1.5192(19) . ?
C11 C12 1.503(2) . ?
C11 C12' 1.528(8) . ?
C12 C13 1.541(3) . ?
C13 C12' 1.516(8) . ?
C13 C14 1.5205(19) . ?
C14 C15 1.346(2) . ?
C15 C17 1.438(2) . ?
C15 C16 1.5130(19) . ?

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
C9 S1 C5 99.47(6) . . ?
C6 C1 C2 119.95(13) . . ?
C3 C2 C1 120.15(13) . . ?
C2 C3 C4 120.72(13) . . ?
C3 C4 C5 118.51(13) . . ?
C3 C4 C7 123.45(13) . . ?
C5 C4 C7 118.04(12) . . ?
C6 C5 C4 121.09(12) . . ?
C6 C5 S1 119.47(10) . . ?
C4 C5 S1 119.42(10) . . ?
C5 C6 C1 119.51(13) . . ?
C4 C7 C8 111.43(12) . . ?
C9 C8 C7 115.13(12) . . ?
C10 C9 C8 120.41(12) . . ?
C10 C9 S1 122.43(11) . . ?
C8 C9 S1 117.15(10) . . ?
C9 C10 C14 131.11(12) . . ?
C9 C10 C11 122.50(13) . . ?
C14 C10 C11 105.53(11) . . ?
C12 C11 C10 102.06(13) . . ?
C12 C11 C12' 28.3(4) . . ?
C10 C11 C12' 107.3(3) . . ?
C11 C12 C13 105.98(15) . . ?
C12' C13 C14 103.2(3) . . ?
C12' C13 C12 28.1(4) . . ?
C14 C13 C12 104.30(12) . . ?
C13 C12' C11 106.0(5) . . ?
C15 C14 C10 128.59(13) . . ?
C15 C14 C13 123.19(13) . . ?
C10 C14 C13 107.58(12) . . ?
C14 C15 C17 120.88(13) . . ?
C14 C15 C16 123.41(13) . . ?
C17 C15 C16 115.17(12) . . ?
N1 C17 C15 175.87(15) . . ?

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
C6 C1 C2 C3 1.3(2) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C3 C4 C5 -2.6(2) . . . . ?
C2 C3 C4 C7 176.85(13) . . . . ?
C3 C4 C5 C6 2.9(2) . . . . ?
C7 C4 C5 C6 -176.64(12) . . . . ?
C3 C4 C5 S1 -178.78(10) . . . . ?
C7 C4 C5 S1 1.70(17) . . . . ?
C9 S1 C5 C6 -140.29(11) . . . . ?
C9 S1 C5 C4 41.35(12) . . . . ?
C4 C5 C6 C1 -1.1(2) . . . . ?
S1 C5 C6 C1 -179.41(10) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C3 C4 C7 C8 126.32(14) . . . . ?
C5 C4 C7 C8 -54.18(17) . . . . ?
C4 C7 C8 C9 53.74(17) . . . . ?
C7 C8 C9 C10 178.18(13) . . . . ?
C7 C8 C9 S1 -3.19(17) . . . . ?
C5 S1 C9 C10 139.60(12) . . . . ?
C5 S1 C9 C8 -38.99(12) . . . . ?
C8 C9 C10 C14 174.39(14) . . . . ?
S1 C9 C10 C14 -4.2(2) . . . . ?
C8 C9 C10 C11 6.6(2) . . . . ?
S1 C9 C10 C11 -171.95(11) . . . . ?
C9 C10 C11 C12 132.59(18) . . . . ?
C14 C10 C11 C12 -37.89(18) . . . . ?
C9 C10 C11 C12' 161.4(5) . . . . ?
C14 C10 C11 C12' -9.1(5) . . . . ?
C10 C11 C12 C13 34.9(2) . . . . ?
C12' C11 C12 C13 -69.3(7) . . . . ?
C11 C12 C13 C12' 71.8(7) . . . . ?
C11 C12 C13 C14 -19.4(2) . . . . ?
C14 C13 C12' C11 26.6(8) . . . . ?
C12 C13 C12' C11 -69.2(7) . . . . ?
C12 C11 C12' C13 71.9(8) . . . . ?
C10 C11 C12' C13 -11.4(8) . . . . ?
C9 C10 C14 C15 46.2(2) . . . . ?
C11 C10 C14 C15 -144.46(15) . . . . ?
C9 C10 C14 C13 -142.90(16) . . . . ?
C11 C10 C14 C13 26.43(15) . . . . ?
C12' C13 C14 C15 138.1(5) . . . . ?
C12 C13 C14 C15 167.04(16) . . . . ?
C12' C13 C14 C10 -33.4(5) . . . . ?
C12 C13 C14 C10 -4.45(18) . . . . ?
C10 C14 C15 C17 4.5(2) . . . . ?
C13 C14 C15 C17 -165.08(13) . . . . ?
C10 C14 C15 C16 175.66(13) . . . . ?
C13 C14 C15 C16 6.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.056


# end of cif file
