# 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_burtwi_5
_database_code_depnum_ccdc_archive 'CCDC 1969696'
loop_
_audit_author_name
_audit_author_address
'Peter G. Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 N S Si'
_chemical_formula_weight         309.49

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.52831(11)
_cell_length_b                   10.39109(14)
_cell_length_c                   11.21545(16)
_cell_angle_alpha                117.5842(14)
_cell_angle_beta                 92.3119(11)
_cell_angle_gamma                95.1854(11)
_cell_volume                     873.50(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    44470
_cell_measurement_theta_min      3.0460
_cell_measurement_theta_max      34.1460

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.247
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93004
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, Hy'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            12628
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.019
_diffrn_reflns_theta_max         34.093
_diffrn_reflns_theta_full        33.000
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             12628
_reflns_number_gt                11145
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-2017
_refine_special_details          
;Refined as a 2-component twin. The components were related by 180 degree
 rotation about the a axis. The relative volume of the smaller component
 refined to 0.4553(6).

 The dataset comprised non-overlapped reflections from both components as
 well as overlapped reflections.,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+0.0939P] 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         12628
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.16610(3) 0.65295(2) 0.57773(2) 0.01995(6) Uani 1 1 d . . . . .
Si1 Si 0.28905(3) 0.23571(2) 0.57593(2) 0.01915(6) Uani 1 1 d . . . . .
N1 N 0.29086(10) 0.34232(9) 0.29502(8) 0.02613(15) Uani 1 1 d . . . . .
C1 C 0.22171(10) 0.82580(8) 0.72237(8) 0.01771(13) Uani 1 1 d . . . . .
C2 C 0.38045(10) 0.88398(10) 0.75529(9) 0.02270(15) Uani 1 1 d . . . . .
H2 H 0.458512 0.831349 0.701068 0.027 Uiso 1 1 calc R U . . .
C3 C 0.42435(12) 1.01945(10) 0.86783(10) 0.02680(17) Uani 1 1 d . . . . .
H3 H 0.532573 1.059289 0.890719 0.032 Uiso 1 1 calc R U . . .
C4 C 0.30987(13) 1.09653(10) 0.94683(9) 0.02682(18) Uani 1 1 d . . . . .
H4 H 0.339925 1.188811 1.023902 0.032 Uiso 1 1 calc R U . . .
C5 C 0.15179(12) 1.03866(10) 0.91308(10) 0.02597(17) Uani 1 1 d . . . . .
H5 H 0.073809 1.092090 0.966771 0.031 Uiso 1 1 calc R U . . .
C6 C 0.10653(10) 0.90288(9) 0.80112(9) 0.02142(15) Uani 1 1 d . . . . .
H6 H -0.001735 0.863153 0.778614 0.026 Uiso 1 1 calc R U . . .
C7 C 0.22672(9) 0.53023(8) 0.63383(8) 0.01617(13) Uani 1 1 d . . . . .
C8 C 0.08157(10) 0.60288(9) 0.84051(8) 0.02007(15) Uani 1 1 d . . . . .
H8 H -0.012948 0.595560 0.788775 0.024 Uiso 1 1 calc R U . . .
C9 C 0.07927(11) 0.64112(10) 0.97675(9) 0.02344(16) Uani 1 1 d . . . . .
H9 H -0.017428 0.658216 1.017535 0.028 Uiso 1 1 calc R U . . .
C10 C 0.21773(12) 0.65449(10) 1.05361(9) 0.02517(17) Uani 1 1 d . . . . .
H10 H 0.215487 0.680423 1.146575 0.030 Uiso 1 1 calc R U . . .
C11 C 0.35942(11) 0.62984(10) 0.99420(9) 0.02369(16) Uani 1 1 d . . . . .
H11 H 0.454149 0.639741 1.046877 0.028 Uiso 1 1 calc R U . . .
C12 C 0.36290(10) 0.59054(9) 0.85721(8) 0.01975(14) Uani 1 1 d . . . . .
H12 H 0.459940 0.574311 0.816903 0.024 Uiso 1 1 calc R U . . .
C13 C 0.22354(9) 0.57519(8) 0.77981(8) 0.01683(13) Uani 1 1 d . . . . .
C14 C 0.26559(9) 0.39753(9) 0.54325(8) 0.01710(13) Uani 1 1 d . . . . .
C15 C 0.27774(10) 0.37075(9) 0.40652(8) 0.01935(14) Uani 1 1 d . . . . .
C16 C 0.16120(13) 0.23613(11) 0.70698(11) 0.02958(19) Uani 1 1 d . . . . .
H16A H 0.158763 0.142314 0.708259 0.044 Uiso 1 1 calc R U . . .
H16B H 0.053700 0.250715 0.685858 0.044 Uiso 1 1 calc R U . . .
H16C H 0.203912 0.315596 0.795721 0.044 Uiso 1 1 calc R U . . .
C17 C 0.50091(12) 0.23678(11) 0.62542(10) 0.02796(18) Uani 1 1 d . . . . .
H17A H 0.537823 0.328378 0.707210 0.042 Uiso 1 1 calc R U . . .
H17B H 0.564552 0.228659 0.551966 0.042 Uiso 1 1 calc R U . . .
H17C H 0.511602 0.153879 0.643079 0.042 Uiso 1 1 calc R U . . .
C18 C 0.22164(12) 0.06699(10) 0.41381(10) 0.02785(18) Uani 1 1 d . . . . .
H18A H 0.237258 -0.019580 0.424407 0.042 Uiso 1 1 calc R U . . .
H18B H 0.283084 0.067262 0.341933 0.042 Uiso 1 1 calc R U . . .
H18C H 0.109224 0.064788 0.390062 0.042 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 C7 1.7678(8) . ?
S1 C1 1.7799(8) . ?
Si1 C16 1.8636(10) . ?
Si1 C17 1.8661(10) . ?
Si1 C18 1.8686(10) . ?
Si1 C14 1.9046(8) . ?
N1 C15 1.1571(11) . ?
C1 C2 1.3927(12) . ?
C1 C6 1.3941(11) . ?
C2 C3 1.3914(13) . ?
C3 C4 1.3906(14) . ?
C4 C5 1.3870(15) . ?
C5 C6 1.3922(13) . ?
C7 C14 1.3623(11) . ?
C7 C13 1.4823(10) . ?
C8 C9 1.3909(11) . ?
C8 C13 1.4001(11) . ?
C9 C10 1.3907(14) . ?
C10 C11 1.3902(13) . ?
C11 C12 1.3974(11) . ?
C12 C13 1.3950(11) . ?
C14 C15 1.4361(11) . ?

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
C7 S1 C1 102.20(4) . . ?
C16 Si1 C17 110.98(5) . . ?
C16 Si1 C18 107.98(5) . . ?
C17 Si1 C18 109.70(5) . . ?
C16 Si1 C14 111.41(4) . . ?
C17 Si1 C14 110.07(4) . . ?
C18 Si1 C14 106.58(4) . . ?
C2 C1 C6 120.37(8) . . ?
C2 C1 S1 119.60(6) . . ?
C6 C1 S1 120.03(7) . . ?
C3 C2 C1 119.79(8) . . ?
C4 C3 C2 120.02(9) . . ?
C5 C4 C3 119.99(8) . . ?
C4 C5 C6 120.50(8) . . ?
C5 C6 C1 119.33(8) . . ?
C14 C7 C13 122.73(7) . . ?
C14 C7 S1 120.10(6) . . ?
C13 C7 S1 117.07(6) . . ?
C9 C8 C13 119.83(8) . . ?
C10 C9 C8 120.37(8) . . ?
C11 C10 C9 119.91(8) . . ?
C10 C11 C12 120.19(8) . . ?
C13 C12 C11 119.84(8) . . ?
C12 C13 C8 119.84(7) . . ?
C12 C13 C7 119.80(7) . . ?
C8 C13 C7 120.37(7) . . ?
C7 C14 C15 117.78(7) . . ?
C7 C14 Si1 126.25(6) . . ?
C15 C14 Si1 115.75(6) . . ?
N1 C15 C14 176.32(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 S1 C1 C2 74.88(7) . . . . ?
C7 S1 C1 C6 -105.83(7) . . . . ?
C6 C1 C2 C3 0.35(13) . . . . ?
S1 C1 C2 C3 179.64(7) . . . . ?
C1 C2 C3 C4 -0.20(14) . . . . ?
C2 C3 C4 C5 -0.29(14) . . . . ?
C3 C4 C5 C6 0.63(14) . . . . ?
C4 C5 C6 C1 -0.48(13) . . . . ?
C2 C1 C6 C5 -0.01(12) . . . . ?
S1 C1 C6 C5 -179.30(6) . . . . ?
C1 S1 C7 C14 -152.99(7) . . . . ?
C1 S1 C7 C13 30.51(7) . . . . ?
C13 C8 C9 C10 1.11(13) . . . . ?
C8 C9 C10 C11 0.14(13) . . . . ?
C9 C10 C11 C12 -0.51(14) . . . . ?
C10 C11 C12 C13 -0.38(13) . . . . ?
C11 C12 C13 C8 1.63(12) . . . . ?
C11 C12 C13 C7 -178.62(8) . . . . ?
C9 C8 C13 C12 -1.99(12) . . . . ?
C9 C8 C13 C7 178.25(7) . . . . ?
C14 C7 C13 C12 63.80(11) . . . . ?
S1 C7 C13 C12 -119.80(7) . . . . ?
C14 C7 C13 C8 -116.45(9) . . . . ?
S1 C7 C13 C8 59.95(9) . . . . ?
C13 C7 C14 C15 -174.83(7) . . . . ?
S1 C7 C14 C15 8.88(10) . . . . ?
C13 C7 C14 Si1 10.73(11) . . . . ?
S1 C7 C14 Si1 -165.57(4) . . . . ?

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_buerg8
_database_code_depnum_ccdc_archive 'CCDC 1969697'
loop_
_audit_author_name
_audit_author_address
'Peter G. Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O S'
_chemical_formula_weight         279.34

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                   20.6204(8)
_cell_length_b                   9.4103(3)
_cell_length_c                   16.7239(6)
_cell_angle_alpha                90
_cell_angle_beta                 120.205(5)
_cell_angle_gamma                90
_cell_volume                     2804.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    46029
_cell_measurement_theta_min      2.7870
_cell_measurement_theta_max      36.1180

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.225
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, Hy'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            70418
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.521
_diffrn_reflns_theta_max         36.042
_diffrn_reflns_theta_full        35.000
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             6266
_reflns_number_gt                5527
_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       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-2017
_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)+(0.0522P)²+1.1797P] 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         6266
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0897
_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_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 0.24782(2) 0.58911(2) 0.07112(2) 0.01602(5) Uani 1 1 d . . . . .
O1 O 0.31939(3) 0.31295(5) 0.06662(3) 0.01413(9) Uani 1 1 d . . . . .
C1 C 0.34204(3) 0.55990(7) 0.10185(4) 0.01255(10) Uani 1 1 d . . . . .
C2 C 0.38885(4) 0.67811(7) 0.12285(5) 0.01463(11) Uani 1 1 d . . . . .
H2 H 0.370869 0.769939 0.125474 0.018 Uiso 1 1 calc R U . . .
C3 C 0.46183(4) 0.66149(8) 0.13993(5) 0.01657(12) Uani 1 1 d . . . . .
H3 H 0.493088 0.742390 0.152604 0.020 Uiso 1 1 calc R U . . .
C4 C 0.48921(4) 0.52677(8) 0.13853(5) 0.01737(12) Uani 1 1 d . . . . .
H4 H 0.539468 0.515594 0.151850 0.021 Uiso 1 1 calc R U . . .
C5 C 0.44283(4) 0.40841(7) 0.11759(5) 0.01543(11) Uani 1 1 d . . . . .
H5 H 0.461494 0.316376 0.116952 0.019 Uiso 1 1 calc R U . . .
C6 C 0.36904(4) 0.42528(7) 0.09757(4) 0.01232(10) Uani 1 1 d . . . . .
C7 C 0.33032(4) 0.20959(7) 0.13541(5) 0.01460(11) Uani 1 1 d . . . . .
H7A H 0.377904 0.158220 0.155050 0.018 Uiso 1 1 calc R U . . .
H7B H 0.288978 0.139402 0.107754 0.018 Uiso 1 1 calc R U . . .
C8 C 0.33285(3) 0.27527(7) 0.21928(4) 0.01218(10) Uani 1 1 d . . . . .
C9 C 0.38392(4) 0.22213(7) 0.30696(5) 0.01536(11) Uani 1 1 d . . . . .
H9 H 0.416386 0.146385 0.312481 0.018 Uiso 1 1 calc R U . . .
C10 C 0.38791(4) 0.27847(8) 0.38623(5) 0.01864(13) Uani 1 1 d . . . . .
H10 H 0.422422 0.240381 0.445256 0.022 Uiso 1 1 calc R U . . .
C11 C 0.34137(5) 0.39051(8) 0.37895(5) 0.01953(13) Uani 1 1 d . . . . .
H11 H 0.344356 0.430009 0.432983 0.023 Uiso 1 1 calc R U . . .
C12 C 0.29027(4) 0.44469(8) 0.29202(5) 0.01653(12) Uani 1 1 d . . . . .
H12 H 0.258606 0.521561 0.287134 0.020 Uiso 1 1 calc R U . . .
C13 C 0.28510(4) 0.38710(7) 0.21186(4) 0.01238(10) Uani 1 1 d . . . . .
C14 C 0.22629(3) 0.44436(7) 0.12063(4) 0.01245(10) Uani 1 1 d . . . . .
C15 C 0.15428(4) 0.40000(7) 0.08115(5) 0.01455(11) Uani 1 1 d . . . . .
C16 C 0.12470(4) 0.29407(9) 0.12268(6) 0.02264(14) Uani 1 1 d . . . . .
H16A H 0.166213 0.258652 0.181291 0.034 Uiso 1 1 calc R U . . .
H16B H 0.101229 0.214482 0.079790 0.034 Uiso 1 1 calc R U . . .
H16C H 0.087437 0.340250 0.133946 0.034 Uiso 1 1 calc R U . . .
C17 C 0.09820(4) 0.45629(7) -0.00682(5) 0.01661(12) Uani 1 1 d . . . . .
N1 N 0.04970(4) 0.49370(7) -0.07760(5) 0.02254(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
S1 C14 1.7631(7) . ?
S1 C1 1.7634(6) . ?
O1 C6 1.3784(8) . ?
O1 C7 1.4352(8) . ?
C1 C2 1.3969(9) . ?
C1 C6 1.4000(9) . ?
C2 C3 1.3920(9) . ?
C3 C4 1.3928(10) . ?
C4 C5 1.3931(10) . ?
C5 C6 1.3929(9) . ?
C7 C8 1.5094(9) . ?
C8 C9 1.3984(9) . ?
C8 C13 1.4034(9) . ?
C9 C10 1.3912(10) . ?
C10 C11 1.3893(11) . ?
C11 C12 1.3937(10) . ?
C12 C13 1.3995(9) . ?
C13 C14 1.4923(9) . ?
C14 C15 1.3523(9) . ?
C15 C17 1.4389(10) . ?
C15 C16 1.5080(10) . ?
C17 N1 1.1551(10) . ?

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
C14 S1 C1 104.10(3) . . ?
C6 O1 C7 115.55(5) . . ?
C2 C1 C6 119.42(6) . . ?
C2 C1 S1 118.02(5) . . ?
C6 C1 S1 122.29(5) . . ?
C3 C2 C1 120.07(6) . . ?
C2 C3 C4 120.28(6) . . ?
C3 C4 C5 119.94(6) . . ?
C6 C5 C4 119.88(6) . . ?
O1 C6 C5 121.20(6) . . ?
O1 C6 C1 118.28(6) . . ?
C5 C6 C1 120.34(6) . . ?
O1 C7 C8 112.67(5) . . ?
C9 C8 C13 119.05(6) . . ?
C9 C8 C7 118.93(6) . . ?
C13 C8 C7 122.02(6) . . ?
C10 C9 C8 121.01(6) . . ?
C11 C10 C9 119.91(6) . . ?
C10 C11 C12 119.70(7) . . ?
C11 C12 C13 120.72(7) . . ?
C12 C13 C8 119.59(6) . . ?
C12 C13 C14 118.07(6) . . ?
C8 C13 C14 122.30(6) . . ?
C15 C14 C13 121.04(6) . . ?
C15 C14 S1 118.90(5) . . ?
C13 C14 S1 119.47(5) . . ?
C14 C15 C17 120.38(6) . . ?
C14 C15 C16 125.33(6) . . ?
C17 C15 C16 114.27(6) . . ?
N1 C17 C15 174.96(8) . . ?

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
C14 S1 C1 C2 -143.49(5) . . . . ?
C14 S1 C1 C6 42.48(6) . . . . ?
C6 C1 C2 C3 -0.43(10) . . . . ?
S1 C1 C2 C3 -174.64(5) . . . . ?
C1 C2 C3 C4 -1.64(10) . . . . ?
C2 C3 C4 C5 1.68(11) . . . . ?
C3 C4 C5 C6 0.37(11) . . . . ?
C7 O1 C6 C5 74.58(8) . . . . ?
C7 O1 C6 C1 -110.18(7) . . . . ?
C4 C5 C6 O1 172.69(6) . . . . ?
C4 C5 C6 C1 -2.46(10) . . . . ?
C2 C1 C6 O1 -172.80(6) . . . . ?
S1 C1 C6 O1 1.15(8) . . . . ?
C2 C1 C6 C5 2.48(9) . . . . ?
S1 C1 C6 C5 176.43(5) . . . . ?
C6 O1 C7 C8 52.99(7) . . . . ?
O1 C7 C8 C9 -141.07(6) . . . . ?
O1 C7 C8 C13 39.50(8) . . . . ?
C13 C8 C9 C10 -0.05(10) . . . . ?
C7 C8 C9 C10 -179.49(6) . . . . ?
C8 C9 C10 C11 -0.86(10) . . . . ?
C9 C10 C11 C12 0.76(11) . . . . ?
C10 C11 C12 C13 0.25(11) . . . . ?
C11 C12 C13 C8 -1.16(10) . . . . ?
C11 C12 C13 C14 176.58(6) . . . . ?
C9 C8 C13 C12 1.05(9) . . . . ?
C7 C8 C13 C12 -179.53(6) . . . . ?
C9 C8 C13 C14 -176.59(6) . . . . ?
C7 C8 C13 C14 2.83(9) . . . . ?
C12 C13 C14 C15 -80.90(8) . . . . ?
C8 C13 C14 C15 96.78(8) . . . . ?
C12 C13 C14 S1 90.25(7) . . . . ?
C8 C13 C14 S1 -92.07(7) . . . . ?
C1 S1 C14 C15 -152.72(5) . . . . ?
C1 S1 C14 C13 35.94(6) . . . . ?
C13 C14 C15 C17 179.96(6) . . . . ?
S1 C14 C15 C17 8.76(9) . . . . ?
C13 C14 C15 C16 1.23(11) . . . . ?
S1 C14 C15 C16 -169.97(6) . . . . ?

_refine_diff_density_max         0.528
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_buerg9
_database_code_depnum_ccdc_archive 'CCDC 1969698'
loop_
_audit_author_name
_audit_author_address
'Peter G. Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2019-12-03 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O S'
_chemical_formula_weight         293.37

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   13.1964(2)
_cell_length_b                   13.3812(2)
_cell_length_c                   16.7048(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2949.80(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    134348
_cell_measurement_theta_min      2.8480
_cell_measurement_theta_max      36.1200

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, Hy'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            221112
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.487
_diffrn_reflns_theta_max         36.045
_diffrn_reflns_theta_full        35.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6774
_reflns_number_gt                5965
_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       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-2017
_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)+(0.0483P)²+0.7287P] 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         6774
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_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 0.54644(2) 0.56548(2) 0.34224(2) 0.01709(5) Uani 1 1 d . . . . .
O1 O 0.42184(4) 0.68391(4) 0.22559(3) 0.01613(9) Uani 1 1 d . . . . .
C1 C 0.46492(5) 0.51899(5) 0.26713(4) 0.01391(10) Uani 1 1 d . . . . .
C2 C 0.45933(5) 0.41574(5) 0.25618(4) 0.01620(11) Uani 1 1 d . . . . .
H2 H 0.495604 0.372528 0.291030 0.019 Uiso 1 1 calc R U . . .
C3 C 0.40110(5) 0.37552(5) 0.19468(4) 0.01797(12) Uani 1 1 d . . . . .
H3 H 0.398489 0.305230 0.186971 0.022 Uiso 1 1 calc R U . . .
C4 C 0.34667(6) 0.43894(5) 0.14449(4) 0.01831(12) Uani 1 1 d . . . . .
H4 H 0.306269 0.411702 0.102781 0.022 Uiso 1 1 calc R U . . .
C5 C 0.35113(5) 0.54216(5) 0.15511(4) 0.01632(11) Uani 1 1 d . . . . .
H5 H 0.313578 0.585004 0.120810 0.020 Uiso 1 1 calc R U . . .
C6 C 0.41066(5) 0.58264(5) 0.21603(4) 0.01342(10) Uani 1 1 d . . . . .
C7 C 0.32988(5) 0.74208(5) 0.23301(4) 0.01600(11) Uani 1 1 d . . . . .
H7A H 0.272384 0.705066 0.209130 0.019 Uiso 1 1 calc R U . . .
H7B H 0.337460 0.806150 0.203988 0.019 Uiso 1 1 calc R U . . .
C8 C 0.30892(5) 0.76221(5) 0.32135(4) 0.01527(11) Uani 1 1 d . . . . .
H8A H 0.369789 0.792224 0.346278 0.018 Uiso 1 1 calc R U . . .
H8B H 0.252585 0.810690 0.326219 0.018 Uiso 1 1 calc R U . . .
C9 C 0.28152(5) 0.66733(5) 0.36518(4) 0.01337(10) Uani 1 1 d . . . . .
C10 C 0.18064(5) 0.63421(5) 0.36364(4) 0.01663(11) Uani 1 1 d . . . . .
H10 H 0.130972 0.673575 0.337180 0.020 Uiso 1 1 calc R U . . .
C11 C 0.15167(5) 0.54525(6) 0.39989(4) 0.01870(12) Uani 1 1 d . . . . .
H11 H 0.082953 0.524240 0.397993 0.022 Uiso 1 1 calc R U . . .
C12 C 0.22382(5) 0.48692(5) 0.43907(4) 0.01782(11) Uani 1 1 d . . . . .
H12 H 0.204443 0.426358 0.464496 0.021 Uiso 1 1 calc R U . . .
C13 C 0.32429(5) 0.51800(5) 0.44065(4) 0.01561(11) Uani 1 1 d . . . . .
H13 H 0.373617 0.477902 0.466808 0.019 Uiso 1 1 calc R U . . .
C14 C 0.35380(4) 0.60770(5) 0.40416(4) 0.01265(10) Uani 1 1 d . . . . .
C15 C 0.46367(4) 0.63282(5) 0.40605(4) 0.01231(10) Uani 1 1 d . . . . .
C16 C 0.50550(4) 0.69705(5) 0.45928(4) 0.01344(10) Uani 1 1 d . . . . .
C17 C 0.44953(5) 0.75452(7) 0.52254(5) 0.02345(15) Uani 1 1 d . . . . .
H17A H 0.377292 0.737798 0.520183 0.035 Uiso 1 1 calc R U . . .
H17B H 0.458375 0.826320 0.513352 0.035 Uiso 1 1 calc R U . . .
H17C H 0.476391 0.736944 0.575396 0.035 Uiso 1 1 calc R U . . .
C18 C 0.61337(5) 0.71036(5) 0.45753(4) 0.01393(10) Uani 1 1 d . . . . .
N1 N 0.70019(5) 0.72098(5) 0.45683(4) 0.01906(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
S1 C1 1.7659(6) . ?
S1 C15 1.7724(6) . ?
O1 C6 1.3724(8) . ?
O1 C7 1.4471(8) . ?
C1 C2 1.3956(9) . ?
C1 C6 1.4024(9) . ?
C2 C3 1.3912(10) . ?
C3 C4 1.3925(10) . ?
C4 C5 1.3937(10) . ?
C5 C6 1.3952(9) . ?
C7 C8 1.5253(9) . ?
C8 C9 1.5095(9) . ?
C9 C10 1.4033(9) . ?
C9 C14 1.4038(9) . ?
C10 C11 1.3892(10) . ?
C11 C12 1.3943(10) . ?
C12 C13 1.3898(9) . ?
C13 C14 1.4014(9) . ?
C14 C15 1.4887(8) . ?
C15 C16 1.3542(8) . ?
C16 C18 1.4349(9) . ?
C16 C17 1.5013(9) . ?
C18 N1 1.1545(8) . ?

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 S1 C15 103.36(3) . . ?
C6 O1 C7 116.80(5) . . ?
C2 C1 C6 119.63(6) . . ?
C2 C1 S1 118.31(5) . . ?
C6 C1 S1 121.97(5) . . ?
C3 C2 C1 120.60(6) . . ?
C2 C3 C4 119.59(6) . . ?
C3 C4 C5 120.37(6) . . ?
C4 C5 C6 120.09(6) . . ?
O1 C6 C5 121.92(6) . . ?
O1 C6 C1 118.29(6) . . ?
C5 C6 C1 119.72(6) . . ?
O1 C7 C8 109.27(5) . . ?
C9 C8 C7 111.36(5) . . ?
C10 C9 C14 118.27(6) . . ?
C10 C9 C8 118.94(6) . . ?
C14 C9 C8 122.71(6) . . ?
C11 C10 C9 121.58(6) . . ?
C10 C11 C12 119.76(6) . . ?
C13 C12 C11 119.52(6) . . ?
C12 C13 C14 120.87(6) . . ?
C13 C14 C9 119.99(6) . . ?
C13 C14 C15 117.05(5) . . ?
C9 C14 C15 122.91(6) . . ?
C16 C15 C14 123.66(5) . . ?
C16 C15 S1 117.80(5) . . ?
C14 C15 S1 118.21(4) . . ?
C15 C16 C18 118.02(6) . . ?
C15 C16 C17 125.93(6) . . ?
C18 C16 C17 116.03(5) . . ?
N1 C18 C16 179.40(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
C15 S1 C1 C2 -120.91(5) . . . . ?
C15 S1 C1 C6 62.61(6) . . . . ?
C6 C1 C2 C3 0.52(10) . . . . ?
S1 C1 C2 C3 -176.05(5) . . . . ?
C1 C2 C3 C4 -1.05(10) . . . . ?
C2 C3 C4 C5 0.65(11) . . . . ?
C3 C4 C5 C6 0.28(11) . . . . ?
C7 O1 C6 C5 54.56(8) . . . . ?
C7 O1 C6 C1 -128.47(6) . . . . ?
C4 C5 C6 O1 176.11(6) . . . . ?
C4 C5 C6 C1 -0.81(10) . . . . ?
C2 C1 C6 O1 -176.62(6) . . . . ?
S1 C1 C6 O1 -0.19(8) . . . . ?
C2 C1 C6 C5 0.41(9) . . . . ?
S1 C1 C6 C5 176.85(5) . . . . ?
C6 O1 C7 C8 98.09(6) . . . . ?
O1 C7 C8 C9 -67.94(7) . . . . ?
C7 C8 C9 C10 -84.53(7) . . . . ?
C7 C8 C9 C14 92.07(7) . . . . ?
C14 C9 C10 C11 0.41(10) . . . . ?
C8 C9 C10 C11 177.16(6) . . . . ?
C9 C10 C11 C12 0.13(10) . . . . ?
C10 C11 C12 C13 -0.69(10) . . . . ?
C11 C12 C13 C14 0.71(10) . . . . ?
C12 C13 C14 C9 -0.16(10) . . . . ?
C12 C13 C14 C15 -177.59(6) . . . . ?
C10 C9 C14 C13 -0.39(9) . . . . ?
C8 C9 C14 C13 -177.02(6) . . . . ?
C10 C9 C14 C15 176.88(6) . . . . ?
C8 C9 C14 C15 0.25(9) . . . . ?
C13 C14 C15 C16 -99.25(8) . . . . ?
C9 C14 C15 C16 83.41(8) . . . . ?
C13 C14 C15 S1 73.90(7) . . . . ?
C9 C14 C15 S1 -103.44(6) . . . . ?
C1 S1 C15 C16 -164.82(5) . . . . ?
C1 S1 C15 C14 21.62(6) . . . . ?
C14 C15 C16 C18 176.52(6) . . . . ?
S1 C15 C16 C18 3.34(8) . . . . ?
C14 C15 C16 C17 -1.63(11) . . . . ?
S1 C15 C16 C17 -174.81(6) . . . . ?

_refine_diff_density_max         0.533
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.053

