# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_3151
_database_code_depnum_ccdc_archive 'CCDC 1963163'
loop_
_audit_author_name
_audit_author_address
'Ze-Feng Xu'
;Department of Chemistry, Zhejiang Sci Tech University
China
;
_audit_update_record             
;
2019-11-02 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;
_audit_creation_date             2019-09-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N O2 S'
_chemical_formula_sum            'C23 H17 N O2 S'
_chemical_formula_weight         371.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2977(4)
_cell_length_b                   14.8655(6)
_cell_length_c                   12.4569(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.564(4)
_cell_angle_gamma                90
_cell_volume                     1906.82(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    99.96(10)
_cell_measurement_theta_max      30.1620
_cell_measurement_theta_min      1.9620
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.868
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22178
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.403
_diffrn_reflns_theta_min         2.133
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.96(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.868
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  20.00   0.50    2.18    --   10.30  37.00   0.00   66
  2  ω     49.00  86.00   0.50    2.18    --   10.30  37.00   0.00   74
  3  ω    -17.00  61.00   0.50    2.18    --   10.30  19.00-150.00  156
  4  ω    -30.00  57.00   0.50    2.18    --   -9.20  57.00  30.00  174
  5  ω    -26.00  12.00   0.50    2.18    --   -9.20 -99.00-180.00   76
  6  ω    -33.00   6.00   0.50    2.18    --   -9.20  77.00 -90.00   78
  7  ω     35.00  61.00   0.50    2.18    --   -9.20  77.00 -90.00   52
  8  ω    -50.00  33.00   0.50    2.18    --   10.30 -57.00-150.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0667805000
_diffrn_orient_matrix_UB_12      0.0024411000
_diffrn_orient_matrix_UB_13      0.0141503000
_diffrn_orient_matrix_UB_21      -0.0085733000
_diffrn_orient_matrix_UB_22      -0.0352135000
_diffrn_orient_matrix_UB_23      0.0377313000
_diffrn_orient_matrix_UB_31      0.0144470000
_diffrn_orient_matrix_UB_32      -0.0321101000
_diffrn_orient_matrix_UB_33      -0.0402516000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3996
_reflns_number_total             5005
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         5005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.3724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1091
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q)
2.c Idealised Me refined as rotating group:
 C00R(H00A,H00B,H00D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S01 S 0.28250(3) 0.55201(2) 0.70905(2) 0.02801(10) Uani 1 1 d . . . . .
O002 O 0.31381(11) 0.63353(7) 0.76536(8) 0.0379(2) Uani 1 1 d . . . . .
O003 O 0.20109(10) 0.48604(7) 0.75869(8) 0.0394(3) Uani 1 1 d . . . . .
N004 N 0.57581(13) 0.60493(8) 0.56725(10) 0.0387(3) Uani 1 1 d . . . . .
C005 C 0.50004(12) 0.45943(8) 0.77962(10) 0.0241(3) Uani 1 1 d . . . . .
C006 C 0.47122(13) 0.37190(8) 0.81549(10) 0.0269(3) Uani 1 1 d . . . . .
C007 C 0.21646(13) 0.22159(8) 0.64024(11) 0.0283(3) Uani 1 1 d . . . . .
C008 C 0.43513(12) 0.49371(8) 0.67818(10) 0.0244(3) Uani 1 1 d . . . . .
H008 H 0.414622 0.441911 0.632399 0.029 Uiso 1 1 calc R . . . .
C009 C 0.22301(12) 0.57869(9) 0.58073(10) 0.0269(3) Uani 1 1 d . . . . .
C00A C 0.38426(14) 0.31550(8) 0.75520(11) 0.0299(3) Uani 1 1 d . . . . .
C00B C 0.51564(13) 0.55583(9) 0.61685(10) 0.0279(3) Uani 1 1 d . . . . .
C00C C 0.58509(13) 0.51339(9) 0.83815(11) 0.0305(3) Uani 1 1 d . . . . .
H00C H 0.603626 0.571238 0.814351 0.037 Uiso 1 1 calc R . . . .
C00D C 0.30915(14) 0.27232(9) 0.70228(11) 0.0303(3) Uani 1 1 d . . . . .
C00E C 0.12979(15) 0.16367(9) 0.69052(12) 0.0364(3) Uani 1 1 d . . . . .
H00E H 0.131767 0.157852 0.764852 0.044 Uiso 1 1 calc R . . . .
C00F C 0.64232(14) 0.48164(10) 0.93153(11) 0.0352(3) Uani 1 1 d . . . . .
H00F H 0.699801 0.517879 0.970021 0.042 Uiso 1 1 calc R . . . .
C00G C 0.52909(14) 0.34149(9) 0.91062(11) 0.0333(3) Uani 1 1 d . . . . .
H00G H 0.510320 0.284095 0.935799 0.040 Uiso 1 1 calc R . . . .
C00H C 0.61405(14) 0.39584(10) 0.96779(11) 0.0358(3) Uani 1 1 d . . . . .
H00H H 0.652346 0.374687 1.030830 0.043 Uiso 1 1 calc R . . . .
C00I C 0.17388(14) 0.51053(9) 0.51575(12) 0.0333(3) Uani 1 1 d . . . . .
H00I H 0.166642 0.452071 0.541588 0.040 Uiso 1 1 calc R . . . .
C00J C 0.13595(15) 0.53131(10) 0.41192(12) 0.0381(3) Uani 1 1 d . . . . .
H00J H 0.102689 0.486145 0.367910 0.046 Uiso 1 1 calc R . . . .
C00K C 0.14643(14) 0.61808(10) 0.37195(11) 0.0353(3) Uani 1 1 d . . . . .
C00L C 0.23274(16) 0.66596(9) 0.54318(12) 0.0373(3) Uani 1 1 d . . . . .
H00L H 0.264951 0.711286 0.587483 0.045 Uiso 1 1 calc R . . . .
C00M C 0.21230(14) 0.22881(10) 0.52848(12) 0.0352(3) Uani 1 1 d . . . . .
H00M H 0.269362 0.267318 0.493780 0.042 Uiso 1 1 calc R . . . .
C00N C 0.19411(16) 0.68506(10) 0.43918(13) 0.0415(4) Uani 1 1 d . . . . .
H00N H 0.200140 0.743726 0.413796 0.050 Uiso 1 1 calc R . . . .
C00O C 0.12373(16) 0.17898(10) 0.46911(13) 0.0426(4) Uani 1 1 d . . . . .
H00O H 0.122321 0.183482 0.394640 0.051 Uiso 1 1 calc R . . . .
C00P C 0.04101(15) 0.11488(10) 0.63062(14) 0.0415(4) Uani 1 1 d . . . . .
H00P H -0.016787 0.076570 0.664806 0.050 Uiso 1 1 calc R . . . .
C00Q C 0.03762(15) 0.12270(10) 0.51995(14) 0.0428(4) Uani 1 1 d . . . . .
H00Q H -0.022722 0.090001 0.479916 0.051 Uiso 1 1 calc R . . . .
C00R C 0.10637(18) 0.63891(13) 0.25810(13) 0.0510(4) Uani 1 1 d . . . . .
H00A H 0.167795 0.612896 0.209648 0.076 Uiso 1 1 calc GR . . . .
H00B H 0.103996 0.702922 0.248046 0.076 Uiso 1 1 calc GR . . . .
H00D H 0.021767 0.614216 0.244014 0.076 Uiso 1 1 calc GR . . . .


_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
S01 O002 1.4353(10) . ?
S01 O003 1.4343(10) . ?
S01 C008 1.8388(13) . ?
S01 C009 1.7517(13) . ?
N004 C00B 1.1428(18) . ?
C005 C006 1.4084(17) . ?
C005 C008 1.5122(17) . ?
C005 C00C 1.3891(18) . ?
C006 C00A 1.4338(18) . ?
C006 C00G 1.3964(18) . ?
C007 C00D 1.4361(18) . ?
C007 C00E 1.3932(19) . ?
C007 C00M 1.3966(19) . ?
C008 C00B 1.4616(18) . ?
C009 C00I 1.3891(19) . ?
C009 C00L 1.3831(19) . ?
C00A C00D 1.1978(19) . ?
C00C C00F 1.382(2) . ?
C00E C00P 1.380(2) . ?
C00F C00H 1.385(2) . ?
C00G C00H 1.383(2) . ?
C00I C00J 1.382(2) . ?
C00J C00K 1.387(2) . ?
C00K C00N 1.388(2) . ?
C00K C00R 1.505(2) . ?
C00L C00N 1.381(2) . ?
C00M C00O 1.384(2) . ?
C00O C00Q 1.378(2) . ?
C00P C00Q 1.384(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
O002 S01 C008 108.17(6) . . ?
O002 S01 C009 109.25(6) . . ?
O003 S01 O002 119.74(7) . . ?
O003 S01 C008 105.80(6) . . ?
O003 S01 C009 110.34(7) . . ?
C009 S01 C008 101.99(6) . . ?
C006 C005 C008 118.93(11) . . ?
C00C C005 C006 120.04(12) . . ?
C00C C005 C008 121.01(11) . . ?
C005 C006 C00A 120.43(11) . . ?
C00G C006 C005 118.61(12) . . ?
C00G C006 C00A 120.96(12) . . ?
C00E C007 C00D 120.53(13) . . ?
C00E C007 C00M 118.82(13) . . ?
C00M C007 C00D 120.65(12) . . ?
C005 C008 S01 110.84(8) . . ?
C00B C008 S01 107.58(9) . . ?
C00B C008 C005 113.66(11) . . ?
C00I C009 S01 119.26(10) . . ?
C00L C009 S01 119.68(10) . . ?
C00L C009 C00I 120.95(12) . . ?
C00D C00A C006 176.60(14) . . ?
N004 C00B C008 178.19(15) . . ?
C00F C00C C005 120.40(13) . . ?
C00A C00D C007 178.56(15) . . ?
C00P C00E C007 120.37(14) . . ?
C00C C00F C00H 119.99(13) . . ?
C00H C00G C006 120.69(13) . . ?
C00G C00H C00F 120.26(13) . . ?
C00J C00I C009 118.70(13) . . ?
C00I C00J C00K 121.42(13) . . ?
C00J C00K C00N 118.61(13) . . ?
C00J C00K C00R 120.53(14) . . ?
C00N C00K C00R 120.86(14) . . ?
C00N C00L C009 119.27(13) . . ?
C00O C00M C007 120.36(13) . . ?
C00L C00N C00K 121.04(14) . . ?
C00Q C00O C00M 120.21(15) . . ?
C00E C00P C00Q 120.30(14) . . ?
C00O C00Q C00P 119.93(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.652
_oxdiff_exptl_absorpt_empirical_full_min 0.657
####################################################################### 
# 
# 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_exp_3188
_database_code_depnum_ccdc_archive 'CCDC 1963164'
loop_
_audit_author_name
_audit_author_address
'Ze-Feng Xu'
;Department of Chemistry, Zhejiang Sci Tech University
China
;
_audit_update_record             
;
2019-11-02 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;
_audit_creation_date             2019-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N O2 S'
_chemical_formula_sum            'C23 H17 N O2 S'
_chemical_formula_weight         371.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   13.4918(3)
_cell_length_b                   13.9452(2)
_cell_length_c                   19.7586(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3717.50(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6790
_cell_measurement_temperature    293
_cell_measurement_theta_max      74.6510
_cell_measurement_theta_min      4.4730
_shelx_estimated_absorpt_T_max   0.729
_shelx_estimated_absorpt_T_min   0.729
_exptl_absorpt_coefficient_mu    1.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12837
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.009
_diffrn_reflns_theta_min         4.476
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00 -33.00   0.50    0.08    --  -43.18 106.00  88.85  100
  2  ω    -72.00 -24.00   0.50    0.31    --  -90.25  50.00 -91.00   96
  3  ω    -93.00 -30.00   0.50    0.08    --  -43.18 -50.00 121.00  126
  4  ω     85.00 132.00   0.50    0.31    --  109.88  72.00  94.00   94
  5  ω     85.00 138.00   0.50    0.31    --  109.88 -77.00  30.00  106
  6  ω     80.00 106.00   0.50    0.31    --  109.88 -94.00 150.00   52
  7  ω     36.00  73.00   0.50    0.31    --  109.88 -94.00 150.00   74
  8  ω     37.00  78.00   0.50    0.31    --  109.88 -77.00  30.00   82
  9  ω     58.00  90.00   0.50    0.31    --  109.88 -94.00 -90.00   64
 10  ω     98.00 132.00   0.50    0.31    --  109.88 -61.00-150.00   68
 11  ω     45.00  71.00   0.50    0.31    --  109.88 -61.00-150.00   52
 12  ω   -115.00 -71.00   0.50    0.08    --  -43.18-125.00  90.00   88
 13  ω   -115.00 -80.00   0.50    0.08    --  -43.18-125.00 -60.00   70
 14  ω   -141.00 -84.00   0.50    0.31    --  -90.25-120.00-107.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0459418000
_diffrn_orient_matrix_UB_12      -0.0775597000
_diffrn_orient_matrix_UB_13      0.0458134000
_diffrn_orient_matrix_UB_21      0.1035690000
_diffrn_orient_matrix_UB_22      -0.0429967000
_diffrn_orient_matrix_UB_23      0.0120363000
_diffrn_orient_matrix_UB_31      0.0137584000
_diffrn_orient_matrix_UB_32      0.0658594000
_diffrn_orient_matrix_UB_33      0.0619855000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3347
_reflns_number_total             3727
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+1.1632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1370
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C005(H005), C00A(H00A), C00B(H00B), C00C(H00C), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R)
2.b Idealised Me refined as rotating group:
 C00K(H00D,H00E,H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S01 S 0.14091(3) 0.68060(3) 0.39291(2) 0.04822(16) Uani 1 1 d . . . . .
O002 O 0.07743(11) 0.65719(11) 0.33748(8) 0.0628(4) Uani 1 1 d . . . . .
O003 O 0.11698(12) 0.64459(11) 0.45878(7) 0.0628(4) Uani 1 1 d . . . . .
N004 N -0.03963(14) 0.86336(16) 0.42375(10) 0.0693(5) Uani 1 1 d . . . . .
C005 C 0.28988(15) 0.64371(14) 0.30423(9) 0.0535(4) Uani 1 1 d . . . . .
H005 H 0.244065 0.657290 0.270397 0.064 Uiso 1 1 calc R . . . .
C006 C 0.26319(14) 0.65042(12) 0.37193(9) 0.0470(4) Uani 1 1 d . . . . .
C007 C 0.45432(15) 0.59612(14) 0.33773(10) 0.0543(4) Uani 1 1 d . . . . .
C008 C 0.04034(15) 0.84205(14) 0.41279(10) 0.0532(4) Uani 1 1 d . . . . .
C009 C 0.14420(14) 0.81388(13) 0.40199(10) 0.0494(4) Uani 1 1 d . . . . .
C00A C 0.33059(16) 0.63035(14) 0.42276(10) 0.0543(4) Uani 1 1 d . . . . .
H00A H 0.312379 0.635174 0.468025 0.065 Uiso 1 1 calc R . . . .
C00B C 0.38508(16) 0.61669(15) 0.28783(10) 0.0574(5) Uani 1 1 d . . . . .
H00B H 0.403290 0.612136 0.242547 0.069 Uiso 1 1 calc R . . . .
C00C C 0.42542(16) 0.60303(16) 0.40495(10) 0.0574(5) Uani 1 1 d . . . . .
H00C H 0.471019 0.588919 0.438814 0.069 Uiso 1 1 calc R . . . .
C00D C 0.21108(15) 0.83900(14) 0.46205(10) 0.0543(4) Uani 1 1 d . . . . .
C00E C 0.16214(17) 0.86312(14) 0.27152(10) 0.0555(5) Uani 1 1 d . . . . .
C00F C 0.19638(14) 0.86286(13) 0.34235(10) 0.0517(4) Uani 1 1 d . . . . .
C00G C 0.29198(16) 0.88885(14) 0.43799(11) 0.0584(5) Uani 1 1 d . . . . .
C00H C 0.27944(16) 0.90373(14) 0.36547(12) 0.0607(5) Uani 1 1 d . . . . .
H00H H 0.323834 0.937568 0.338528 0.073 Uiso 1 1 calc R . . . .
C00I C 0.06429(18) 0.84098(17) 0.25266(11) 0.0646(5) Uani 1 1 d . . . . .
H00I H 0.018409 0.823542 0.285558 0.078 Uiso 1 1 calc R . . . .
C00J C 0.20031(18) 0.81729(17) 0.52917(11) 0.0664(6) Uani 1 1 d . . . . .
H00J H 0.144100 0.785947 0.545076 0.080 Uiso 1 1 calc R . . . .
C00K C 0.55824(16) 0.56721(19) 0.31956(13) 0.0722(6) Uani 1 1 d . . . . .
H00D H 0.557826 0.534025 0.276989 0.108 Uiso 1 1 calc GR . . . .
H00E H 0.584264 0.525749 0.354028 0.108 Uiso 1 1 calc GR . . . .
H00F H 0.599031 0.623399 0.316035 0.108 Uiso 1 1 calc GR . . . .
C00L C 0.2278(2) 0.88649(19) 0.21979(13) 0.0768(7) Uani 1 1 d . . . . .
H00L H 0.293499 0.899501 0.230642 0.092 Uiso 1 1 calc R . . . .
C00M C 0.36740(18) 0.91546(17) 0.48126(15) 0.0751(7) Uani 1 1 d . . . . .
H00M H 0.422251 0.948870 0.465239 0.090 Uiso 1 1 calc R . . . .
C00N C 0.0357(2) 0.84499(19) 0.18520(12) 0.0739(6) Uani 1 1 d . . . . .
H00N H -0.028886 0.829556 0.172976 0.089 Uiso 1 1 calc R . . . .
C00O C 0.2766(2) 0.8439(2) 0.57286(13) 0.0785(7) Uani 1 1 d . . . . .
H00O H 0.271454 0.829348 0.618667 0.094 Uiso 1 1 calc R . . . .
C00P C 0.3596(2) 0.8912(2) 0.54962(15) 0.0823(8) Uani 1 1 d . . . . .
H00P H 0.410384 0.906891 0.579449 0.099 Uiso 1 1 calc R . . . .
C00Q C 0.1029(3) 0.8717(2) 0.13653(13) 0.0848(8) Uani 1 1 d . . . . .
H00Q H 0.083021 0.876847 0.091611 0.102 Uiso 1 1 calc R . . . .
C00R C 0.1991(3) 0.8909(2) 0.15395(14) 0.0934(9) Uani 1 1 d . . . . .
H00R H 0.244907 0.907044 0.120660 0.112 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
S01 O002 1.4281(15) . ?
S01 O003 1.4319(14) . ?
S01 C006 1.7523(19) . ?
S01 C009 1.8678(19) . ?
N004 C008 1.140(3) . ?
C005 C006 1.388(3) . ?
C005 C00B 1.377(3) . ?
C006 C00A 1.383(3) . ?
C007 C00B 1.388(3) . ?
C007 C00C 1.388(3) . ?
C007 C00K 1.502(3) . ?
C008 C009 1.471(3) . ?
C009 C00D 1.531(3) . ?
C009 C00F 1.533(3) . ?
C00A C00C 1.381(3) . ?
C00D C00G 1.379(3) . ?
C00D C00J 1.368(3) . ?
C00E C00F 1.474(3) . ?
C00E C00I 1.406(3) . ?
C00E C00L 1.391(3) . ?
C00F C00H 1.338(3) . ?
C00G C00H 1.458(3) . ?
C00G C00M 1.380(3) . ?
C00I C00N 1.389(3) . ?
C00J C00O 1.394(3) . ?
C00L C00R 1.359(4) . ?
C00M C00P 1.397(4) . ?
C00N C00Q 1.373(4) . ?
C00O C00P 1.378(4) . ?
C00Q C00R 1.369(5) . ?

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
O002 S01 O003 118.79(10) . . ?
O002 S01 C006 109.17(9) . . ?
O002 S01 C009 108.39(9) . . ?
O003 S01 C006 110.06(9) . . ?
O003 S01 C009 105.49(9) . . ?
C006 S01 C009 103.85(8) . . ?
C00B C005 C006 119.15(18) . . ?
C005 C006 S01 119.22(15) . . ?
C00A C006 S01 119.72(15) . . ?
C00A C006 C005 121.01(18) . . ?
C00B C007 C00K 120.91(19) . . ?
C00C C007 C00B 118.45(19) . . ?
C00C C007 C00K 120.64(19) . . ?
N004 C008 C009 177.4(2) . . ?
C008 C009 S01 104.89(13) . . ?
C008 C009 C00D 112.82(16) . . ?
C008 C009 C00F 115.47(16) . . ?
C00D C009 S01 108.42(13) . . ?
C00D C009 C00F 102.89(16) . . ?
C00F C009 S01 112.36(13) . . ?
C00C C00A C006 118.69(18) . . ?
C005 C00B C007 121.13(18) . . ?
C00A C00C C007 121.57(19) . . ?
C00G C00D C009 108.34(18) . . ?
C00J C00D C009 129.6(2) . . ?
C00J C00D C00G 122.0(2) . . ?
C00I C00E C00F 123.07(19) . . ?
C00L C00E C00F 119.9(2) . . ?
C00L C00E C00I 117.0(2) . . ?
C00E C00F C009 125.94(17) . . ?
C00H C00F C009 108.17(18) . . ?
C00H C00F C00E 125.87(19) . . ?
C00D C00G C00H 108.59(19) . . ?
C00D C00G C00M 120.4(2) . . ?
C00M C00G C00H 131.0(2) . . ?
C00F C00H C00G 111.86(19) . . ?
C00N C00I C00E 120.4(2) . . ?
C00D C00J C00O 117.6(2) . . ?
C00R C00L C00E 122.2(3) . . ?
C00G C00M C00P 118.6(2) . . ?
C00Q C00N C00I 120.0(3) . . ?
C00P C00O C00J 121.4(2) . . ?
C00O C00P C00M 120.0(2) . . ?
C00R C00Q C00N 120.2(3) . . ?
C00L C00R C00Q 120.1(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.691
_oxdiff_exptl_absorpt_empirical_full_min 0.571
