# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mw488_1_a
_database_code_depnum_ccdc_archive 'CCDC 2068877'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H14 O S'
_chemical_formula_sum            'C23 H14 O S'
_chemical_formula_weight         338.40
_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'
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                   12.9474(18)
_cell_length_b                   11.1005(17)
_cell_length_c                   11.7019(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.279(5)
_cell_angle_gamma                90
_cell_volume                     1668.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9174
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.326
_cell_measurement_theta_min      2.425
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0544 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.9341.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.111
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22309
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.412
_diffrn_reflns_theta_min         1.586
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2523
_reflns_number_total             3417
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.027
_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)+(0.0373P)²+0.5874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_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
S1 S 0.23416(4) 0.60733(4) 0.60031(4) 0.04592(15) Uani 1 1 d . . . . .
O1 O 0.07737(12) 0.47688(14) 0.83251(12) 0.0651(4) Uani 1 1 d . . . . .
C1 C 0.22916(13) 0.66981(16) 0.82759(15) 0.0417(4) Uani 1 1 d . . . . .
H1 H 0.202472 0.655264 0.896428 0.050 Uiso 1 1 calc R U . . .
C2 C 0.19376(13) 0.60005(15) 0.73837(15) 0.0384(4) Uani 1 1 d . . . . .
C3 C 0.11758(14) 0.49865(16) 0.74689(16) 0.0422(4) Uani 1 1 d . . . . .
C4 C 0.10267(13) 0.43183(16) 0.63781(15) 0.0397(4) Uani 1 1 d . . . . .
C5 C 0.03972(14) 0.33068(17) 0.61296(18) 0.0508(5) Uani 1 1 d . . . . .
H5 H 0.000770 0.299870 0.667789 0.061 Uiso 1 1 calc R U . . .
C6 C 0.03593(16) 0.27715(18) 0.50670(19) 0.0575(6) Uani 1 1 d . . . . .
H6 H -0.005044 0.209121 0.489566 0.069 Uiso 1 1 calc R U . . .
C7 C 0.09298(17) 0.32442(19) 0.42535(19) 0.0582(6) Uani 1 1 d . . . . .
H7 H 0.089899 0.287161 0.353816 0.070 Uiso 1 1 calc R U . . .
C8 C 0.15467(16) 0.42578(18) 0.44728(17) 0.0510(5) Uani 1 1 d . . . . .
H8 H 0.191920 0.457407 0.391309 0.061 Uiso 1 1 calc R U . . .
C9 C 0.15930(14) 0.47881(15) 0.55524(16) 0.0404(4) Uani 1 1 d . . . . .
C10 C 0.30662(13) 0.76808(15) 0.82831(14) 0.0371(4) Uani 1 1 d . . . . .
C10A C 0.28732(13) 0.87030(15) 0.75702(14) 0.0378(4) Uani 1 1 d . . . . .
C11 C 0.45914(14) 0.94922(16) 0.82958(15) 0.0426(4) Uani 1 1 d . . . . .
H11 H 0.510400 1.007679 0.828047 0.051 Uiso 1 1 calc R U . . .
C11A C 0.36518(14) 0.96277(15) 0.75906(15) 0.0396(4) Uani 1 1 d . . . . .
C12A C 0.40036(13) 0.75884(15) 0.90393(14) 0.0372(4) Uani 1 1 d . . . . .
C12 C 0.42244(15) 0.66153(17) 0.98246(16) 0.0465(5) Uani 1 1 d . . . . .
H12 H 0.373424 0.600688 0.985120 0.056 Uiso 1 1 calc R U . . .
C13 C 0.51370(16) 0.65589(19) 1.05352(17) 0.0530(5) Uani 1 1 d . . . . .
H13 H 0.525725 0.591993 1.104895 0.064 Uiso 1 1 calc R U . . .
C14 C 0.59056(15) 0.74550(19) 1.05060(17) 0.0530(5) Uani 1 1 d . . . . .
H14 H 0.652881 0.739948 1.099471 0.064 Uiso 1 1 calc R U . . .
C15A C 0.47864(13) 0.85065(15) 0.90236(15) 0.0392(4) Uani 1 1 d . . . . .
C15 C 0.57404(14) 0.83899(18) 0.97736(16) 0.0482(5) Uani 1 1 d . . . . .
H15 H 0.625650 0.896983 0.975569 0.058 Uiso 1 1 calc R U . . .
C16 C 0.34388(16) 1.06731(17) 0.68911(17) 0.0501(5) Uani 1 1 d . . . . .
H16 H 0.394664 1.126507 0.688764 0.060 Uiso 1 1 calc R U . . .
C17 C 0.25103(17) 1.08173(19) 0.62328(18) 0.0558(5) Uani 1 1 d . . . . .
H17 H 0.238321 1.150600 0.578443 0.067 Uiso 1 1 calc R U . . .
C18 C 0.17327(16) 0.99220(18) 0.62259(17) 0.0520(5) Uani 1 1 d . . . . .
H18 H 0.109393 1.003130 0.577664 0.062 Uiso 1 1 calc R U . . .
C19 C 0.19053(14) 0.89079(17) 0.68641(15) 0.0446(4) Uani 1 1 d . . . . .
H19 H 0.138200 0.833136 0.684251 0.054 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 C2 1.7619(18) . ?
S1 C9 1.7673(18) . ?
O1 C3 1.211(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.334(2) . ?
C1 C10 1.481(2) . ?
C2 C3 1.508(2) . ?
C3 C4 1.468(3) . ?
C4 C5 1.396(2) . ?
C4 C9 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.388(3) . ?
C10 C10A 1.412(2) . ?
C10 C12A 1.412(2) . ?
C10A C11A 1.437(2) . ?
C10A C19 1.429(2) . ?
C11 H11 0.9300 . ?
C11 C11A 1.389(3) . ?
C11 C15A 1.390(2) . ?
C11A C16 1.427(3) . ?
C12A C12 1.423(2) . ?
C12A C15A 1.439(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.357(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.411(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.346(3) . ?
C15A C15 1.428(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.353(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.414(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.354(3) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C9 91.23(8) . . ?
C2 C1 H1 116.7 . . ?
C2 C1 C10 126.69(16) . . ?
C10 C1 H1 116.7 . . ?
C1 C2 S1 125.36(14) . . ?
C1 C2 C3 122.98(16) . . ?
C3 C2 S1 111.56(12) . . ?
O1 C3 C2 123.86(17) . . ?
O1 C3 C4 126.58(17) . . ?
C4 C3 C2 109.56(15) . . ?
C5 C4 C3 126.62(17) . . ?
C9 C4 C3 113.14(16) . . ?
C9 C4 C5 120.23(18) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 119.94(19) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.84(19) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 121.0 . . ?
C7 C8 C9 118.1(2) . . ?
C9 C8 H8 121.0 . . ?
C4 C9 S1 114.46(14) . . ?
C4 C9 C8 120.60(17) . . ?
C8 C9 S1 124.94(15) . . ?
C10A C10 C1 121.30(15) . . ?
C10A C10 C12A 120.16(15) . . ?
C12A C10 C1 118.53(15) . . ?
C10 C10A C11A 119.54(16) . . ?
C10 C10A C19 123.11(16) . . ?
C19 C10A C11A 117.25(16) . . ?
C11A C11 H11 119.1 . . ?
C11A C11 C15A 121.79(16) . . ?
C15A C11 H11 119.1 . . ?
C11 C11A C10A 119.50(16) . . ?
C11 C11A C16 121.34(17) . . ?
C16 C11A C10A 119.17(16) . . ?
C10 C12A C12 123.09(16) . . ?
C10 C12A C15A 119.43(16) . . ?
C12 C12A C15A 117.48(16) . . ?
C12A C12 H12 119.4 . . ?
C13 C12 C12A 121.24(18) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.97(19) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.24(18) . . ?
C15 C14 H14 119.9 . . ?
C11 C15A C12A 119.46(16) . . ?
C11 C15A C15 121.60(17) . . ?
C15 C15A C12A 118.94(17) . . ?
C14 C15 C15A 121.12(18) . . ?
C14 C15 H15 119.4 . . ?
C15A C15 H15 119.4 . . ?
C11A C16 H16 119.5 . . ?
C17 C16 C11A 121.08(18) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.06(19) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.91(18) . . ?
C19 C18 H18 119.5 . . ?
C10A C19 H19 119.2 . . ?
C18 C19 C10A 121.51(18) . . ?
C18 C19 H19 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C2 C3 O1 -178.63(16) . . . . ?
S1 C2 C3 C4 2.40(18) . . . . ?
O1 C3 C4 C5 -0.3(3) . . . . ?
O1 C3 C4 C9 179.87(19) . . . . ?
C1 C2 C3 O1 4.8(3) . . . . ?
C1 C2 C3 C4 -174.15(17) . . . . ?
C1 C10 C10A C11A -179.07(15) . . . . ?
C1 C10 C10A C19 4.7(3) . . . . ?
C1 C10 C12A C12 -2.3(2) . . . . ?
C1 C10 C12A C15A 177.25(15) . . . . ?
C2 S1 C9 C4 1.67(14) . . . . ?
C2 S1 C9 C8 -178.40(16) . . . . ?
C2 C1 C10 C10A 61.8(3) . . . . ?
C2 C1 C10 C12A -119.4(2) . . . . ?
C2 C3 C4 C5 178.68(17) . . . . ?
C2 C3 C4 C9 -1.2(2) . . . . ?
C3 C4 C5 C6 -178.77(17) . . . . ?
C3 C4 C9 S1 -0.5(2) . . . . ?
C3 C4 C9 C8 179.55(16) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C5 C4 C9 S1 179.59(13) . . . . ?
C5 C4 C9 C8 -0.3(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C8 C9 S1 179.40(14) . . . . ?
C7 C8 C9 C4 -0.7(3) . . . . ?
C9 S1 C2 C1 174.16(17) . . . . ?
C9 S1 C2 C3 -2.29(13) . . . . ?
C9 C4 C5 C6 1.1(3) . . . . ?
C10 C1 C2 S1 1.5(3) . . . . ?
C10 C1 C2 C3 177.59(16) . . . . ?
C10 C10A C11A C11 1.2(2) . . . . ?
C10 C10A C11A C16 -178.29(16) . . . . ?
C10 C10A C19 C18 177.32(17) . . . . ?
C10 C12A C12 C13 179.82(17) . . . . ?
C10 C12A C15A C11 2.4(2) . . . . ?
C10 C12A C15A C15 -178.61(16) . . . . ?
C10A C10 C12A C12 176.55(16) . . . . ?
C10A C10 C12A C15A -3.9(2) . . . . ?
C10A C11A C16 C17 1.5(3) . . . . ?
C11 C11A C16 C17 -177.95(18) . . . . ?
C11 C15A C15 C14 177.47(17) . . . . ?
C11A C10A C19 C18 1.0(3) . . . . ?
C11A C11 C15A C12A 1.0(3) . . . . ?
C11A C11 C15A C15 -177.98(16) . . . . ?
C11A C16 C17 C18 -0.3(3) . . . . ?
C12A C10 C10A C11A 2.2(2) . . . . ?
C12A C10 C10A C19 -174.09(15) . . . . ?
C12A C12 C13 C14 -1.0(3) . . . . ?
C12A C15A C15 C14 -1.5(3) . . . . ?
C12 C12A C15A C11 -178.05(16) . . . . ?
C12 C12A C15A C15 0.9(2) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C15A 0.8(3) . . . . ?
C15A C11 C11A C10A -2.8(3) . . . . ?
C15A C11 C11A C16 176.71(16) . . . . ?
C15A C12A C12 C13 0.3(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C10A 0.2(3) . . . . ?
C19 C10A C11A C11 177.65(16) . . . . ?
C19 C10A C11A C16 -1.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mw482_1
_database_code_depnum_ccdc_archive 'CCDC 2068881'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_mw482_1             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Low quality crystal as a result from continuous heating
at 180 celcius.
;
# end Validation Reply Form
_audit_creation_date             2021-02-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H14 O S'
_chemical_formula_sum            'C23 H14 O S'
_chemical_formula_weight         338.40
_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'
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                   10.453(3)
_cell_length_b                   13.935(4)
_cell_length_c                   11.229(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.990(8)
_cell_angle_gamma                90
_cell_volume                     1593.9(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6855
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.483
_cell_measurement_theta_min      2.366
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_correction_T_min  0.6415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1241 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.8613.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17901
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        22.515
_diffrn_reflns_theta_max         22.515
_diffrn_reflns_theta_min         1.999
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.99
_diffrn_source_power             0.0495
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1568
_reflns_number_total             2085
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2085
_refine_ls_number_restraints     485
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      0.953
_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)+(0.0341P)²+0.3775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0799
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C3B-C9
 1.45 with sigma of 0.02
 C3B-C2
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(S1B)=Sof(O1B)=Sof(C3B)=1-FVAR(1)
 Sof(S1A)=Sof(O1A)=Sof(C3A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_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
C1 C 0.3161(2) 0.57457(17) 0.4951(2) 0.0217(6) Uani 1 1 d . U . . .
H1 H 0.353542 0.570912 0.580283 0.026 Uiso 1 1 calc R U . . .
C2 C 0.2722(2) 0.66125(17) 0.4549(2) 0.0208(6) Uani 1 1 d D U . . .
C4 C 0.1495(2) 0.79053(16) 0.3356(2) 0.0207(6) Uani 1 1 d . U . . .
C5 C 0.0693(2) 0.84182(17) 0.2412(2) 0.0251(6) Uani 1 1 d . U . . .
H5 H 0.038190 0.813197 0.163301 0.030 Uiso 1 1 calc R U . . .
C6 C 0.0357(2) 0.93499(17) 0.2628(2) 0.0246(6) Uani 1 1 d . U . . .
H6 H -0.019819 0.970782 0.199763 0.029 Uiso 1 1 calc R U . . .
C7 C 0.0829(2) 0.97620(17) 0.3760(2) 0.0245(6) Uani 1 1 d . U . . .
H7 H 0.058550 1.040258 0.389654 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1644(2) 0.92699(17) 0.4699(2) 0.0240(6) Uani 1 1 d . U . . .
H8 H 0.197355 0.956518 0.546918 0.029 Uiso 1 1 calc R U . . .
C9 C 0.1966(2) 0.83294(17) 0.4482(2) 0.0221(6) Uani 1 1 d D U . . .
C10A C 0.2591(2) 0.40249(16) 0.4716(2) 0.0206(6) Uani 1 1 d . U . . .
C10 C 0.3157(2) 0.48349(16) 0.4280(2) 0.0188(6) Uani 1 1 d . U . . .
C11 C 0.3381(2) 0.30164(17) 0.3270(2) 0.0235(6) Uani 1 1 d . U . . .
H11 H 0.346722 0.240005 0.293537 0.028 Uiso 1 1 calc R U . . .
C11A C 0.2709(2) 0.31030(16) 0.4195(2) 0.0205(6) Uani 1 1 d . U . . .
C12A C 0.3820(2) 0.47354(16) 0.3324(2) 0.0195(6) Uani 1 1 d . U . . .
C12 C 0.4450(2) 0.55147(17) 0.2850(2) 0.0235(6) Uani 1 1 d . U . . .
H12 H 0.440277 0.614137 0.317087 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5108(2) 0.53780(18) 0.1957(2) 0.0275(6) Uani 1 1 d . U . . .
H13 H 0.550242 0.591222 0.165472 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5223(2) 0.44564(18) 0.1464(2) 0.0280(6) Uani 1 1 d . U . . .
H14 H 0.569945 0.437052 0.084446 0.034 Uiso 1 1 calc R U . . .
C15A C 0.3934(2) 0.38035(16) 0.2818(2) 0.0204(6) Uani 1 1 d . U . . .
C15 C 0.4646(2) 0.36978(18) 0.1886(2) 0.0255(6) Uani 1 1 d . U . . .
H15 H 0.471854 0.307968 0.155040 0.031 Uiso 1 1 calc R U . . .
C16 C 0.2113(2) 0.22953(17) 0.4643(2) 0.0260(6) Uani 1 1 d . U . . .
H16 H 0.219179 0.167809 0.430744 0.031 Uiso 1 1 calc R U . . .
C17 C 0.1442(2) 0.23908(18) 0.5530(2) 0.0281(6) Uani 1 1 d . U . . .
H17 H 0.105397 0.184478 0.581323 0.034 Uiso 1 1 calc R U . . .
C18 C 0.1316(2) 0.33065(18) 0.6040(2) 0.0283(6) Uani 1 1 d . U . . .
H18 H 0.083804 0.337067 0.666169 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1869(2) 0.40923(17) 0.5651(2) 0.0242(6) Uani 1 1 d . U . . .
H19 H 0.177395 0.469911 0.600678 0.029 Uiso 1 1 calc R U . . .
S1A S 0.29848(12) 0.76037(7) 0.55895(12) 0.0208(6) Uani 0.820(7) 1 d . U P A 1
O1A O 0.1542(4) 0.6319(3) 0.2504(4) 0.0247(10) Uani 0.820(7) 1 d . U P A 1
C3A C 0.1900(7) 0.6899(5) 0.3379(5) 0.0174(13) Uani 0.820(7) 1 d . U P A 1
S1B S 0.1753(8) 0.6693(6) 0.2882(7) 0.027(2) Uani 0.180(7) 1 d . U P A 2
O1B O 0.335(2) 0.7561(12) 0.620(2) 0.088(7) Uani 0.180(7) 1 d . U P A 2
C3B C 0.265(3) 0.7493(12) 0.5150(19) 0.040(5) Uani 0.180(7) 1 d D U P A 2


_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 H1 0.9500 . ?
C1 C2 1.334(3) . ?
C1 C10 1.476(3) . ?
C2 S1A 1.790(2) . ?
C2 C3A 1.455(6) . ?
C2 S1B 1.922(8) . ?
C2 C3B 1.410(16) . ?
C4 C5 1.392(3) . ?
C4 C9 1.382(3) . ?
C4 C3A 1.463(6) . ?
C4 S1B 1.810(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.381(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(3) . ?
C9 S1A 1.763(3) . ?
C9 C3B 1.482(16) . ?
C10A C10 1.413(3) . ?
C10A C11A 1.428(3) . ?
C10A C19 1.427(3) . ?
C10 C12A 1.409(3) . ?
C11 H11 0.9500 . ?
C11 C11A 1.384(3) . ?
C11 C15A 1.388(3) . ?
C11A C16 1.432(3) . ?
C12A C12 1.433(3) . ?
C12A C15A 1.433(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.351(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.414(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.354(3) . ?
C15A C15 1.421(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.347(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.417(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.356(3) . ?
C19 H19 0.9500 . ?
O1A C3A 1.263(9) . ?
O1B C3B 1.24(4) . ?

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 H1 114.9 . . ?
C2 C1 C10 130.2(2) . . ?
C10 C1 H1 114.9 . . ?
C1 C2 S1A 119.18(19) . . ?
C1 C2 C3A 130.0(3) . . ?
C1 C2 S1B 116.6(3) . . ?
C1 C2 C3B 132.6(8) . . ?
C3A C2 S1A 110.5(3) . . ?
C3B C2 S1B 110.1(8) . . ?
C5 C4 C3A 128.9(3) . . ?
C5 C4 S1B 111.0(3) . . ?
C9 C4 C5 120.5(2) . . ?
C9 C4 C3A 110.6(3) . . ?
C9 C4 S1B 128.5(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(2) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 121.1 . . ?
C7 C8 C9 117.9(2) . . ?
C9 C8 H8 121.1 . . ?
C4 C9 C8 120.9(2) . . ?
C4 C9 S1A 115.76(18) . . ?
C4 C9 C3B 99.2(8) . . ?
C8 C9 S1A 123.3(2) . . ?
C8 C9 C3B 139.7(8) . . ?
C10 C10A C11A 119.7(2) . . ?
C10 C10A C19 122.3(2) . . ?
C19 C10A C11A 118.0(2) . . ?
C10A C10 C1 117.6(2) . . ?
C12A C10 C1 121.9(2) . . ?
C12A C10 C10A 120.1(2) . . ?
C11A C11 H11 119.0 . . ?
C11A C11 C15A 122.0(2) . . ?
C15A C11 H11 119.0 . . ?
C10A C11A C16 118.6(2) . . ?
C11 C11A C10A 119.4(2) . . ?
C11 C11A C16 122.0(2) . . ?
C10 C12A C12 123.6(2) . . ?
C10 C12A C15A 119.4(2) . . ?
C12 C12A C15A 116.9(2) . . ?
C12A C12 H12 119.3 . . ?
C13 C12 C12A 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 H14 120.4 . . ?
C11 C15A C12A 119.5(2) . . ?
C11 C15A C15 121.2(2) . . ?
C15 C15A C12A 119.3(2) . . ?
C14 C15 C15A 121.6(2) . . ?
C14 C15 H15 119.2 . . ?
C15A C15 H15 119.2 . . ?
C11A C16 H16 119.3 . . ?
C17 C16 C11A 121.5(2) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.9(2) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C10A C19 H19 119.4 . . ?
C18 C19 C10A 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C9 S1A C2 90.15(13) . . ?
C2 C3A C4 112.9(4) . . ?
O1A C3A C2 122.6(5) . . ?
O1A C3A C4 124.4(5) . . ?
C4 S1B C2 81.3(3) . . ?
C2 C3B C9 120.9(14) . . ?
O1B C3B C2 116.0(15) . . ?
O1B C3B C9 122.3(16) . . ?

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
C1 C2 S1A C9 -171.65(19) . . . . ?
C1 C2 C3A C4 172.4(3) . . . . ?
C1 C2 C3A O1A -4.9(10) . . . . ?
C1 C2 C3B C9 -172.8(11) . . . . ?
C1 C2 C3B O1B 17(4) . . . . ?
C1 C10 C12A C12 -5.6(4) . . . . ?
C1 C10 C12A C15A 171.5(2) . . . . ?
C2 C1 C10 C10A -126.5(3) . . . . ?
C2 C1 C10 C12A 60.6(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C4 C9 S1A C2 -3.51(19) . . . . ?
C4 C9 C3B C2 3(3) . . . . ?
C4 C9 C3B O1B 173(3) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C5 C4 C9 S1A -179.34(18) . . . . ?
C5 C4 C9 C3B 176.2(13) . . . . ?
C5 C4 C3A C2 -178.5(3) . . . . ?
C5 C4 C3A O1A -1.3(10) . . . . ?
C5 C4 S1B C2 -177.8(2) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C7 C8 C9 C4 0.6(3) . . . . ?
C7 C8 C9 S1A -179.52(17) . . . . ?
C7 C8 C9 C3B -173(2) . . . . ?
C8 C9 S1A C2 176.6(2) . . . . ?
C8 C9 C3B C2 177.8(9) . . . . ?
C8 C9 C3B O1B -13(5) . . . . ?
C9 C4 C5 C6 -1.2(3) . . . . ?
C9 C4 C3A C2 -2.0(6) . . . . ?
C9 C4 C3A O1A 175.3(7) . . . . ?
C9 C4 S1B C2 1.2(5) . . . . ?
C10A C10 C12A C12 -178.4(2) . . . . ?
C10A C10 C12A C15A -1.2(3) . . . . ?
C10A C11A C16 C17 0.5(3) . . . . ?
C10 C1 C2 S1A -175.35(19) . . . . ?
C10 C1 C2 C3A 12.2(5) . . . . ?
C10 C1 C2 S1B 7.9(4) . . . . ?
C10 C1 C2 C3B 177.1(18) . . . . ?
C10 C10A C11A C11 0.2(3) . . . . ?
C10 C10A C11A C16 -179.3(2) . . . . ?
C10 C10A C19 C18 178.9(2) . . . . ?
C10 C12A C12 C13 177.9(2) . . . . ?
C10 C12A C15A C11 0.5(3) . . . . ?
C10 C12A C15A C15 -177.6(2) . . . . ?
C11 C11A C16 C17 -178.9(2) . . . . ?
C11 C15A C15 C14 -178.0(2) . . . . ?
C11A C10A C10 C1 -172.2(2) . . . . ?
C11A C10A C10 C12A 0.8(3) . . . . ?
C11A C10A C19 C18 0.4(3) . . . . ?
C11A C11 C15A C12A 0.5(4) . . . . ?
C11A C11 C15A C15 178.6(2) . . . . ?
C11A C16 C17 C18 0.0(4) . . . . ?
C12A C12 C13 C14 -1.0(4) . . . . ?
C12A C15A C15 C14 0.1(3) . . . . ?
C12 C12A C15A C11 177.9(2) . . . . ?
C12 C12A C15A C15 -0.3(3) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C13 C14 C15 C15A -0.4(4) . . . . ?
C15A C11 C11A C10A -0.9(3) . . . . ?
C15A C11 C11A C16 178.5(2) . . . . ?
C15A C12A C12 C13 0.7(3) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C10A 0.2(4) . . . . ?
C19 C10A C10 C1 9.3(3) . . . . ?
C19 C10A C10 C12A -177.7(2) . . . . ?
C19 C10A C11A C11 178.8(2) . . . . ?
C19 C10A C11A C16 -0.7(3) . . . . ?
S1A C2 C3A C4 -0.5(6) . . . . ?
S1A C2 C3A O1A -177.8(7) . . . . ?
C3A C2 S1A C9 2.2(3) . . . . ?
C3A C4 C5 C6 175.0(4) . . . . ?
C3A C4 C9 C8 -176.4(4) . . . . ?
C3A C4 C9 S1A 3.8(4) . . . . ?
S1B C2 C3B C9 -3(3) . . . . ?
S1B C2 C3B O1B -173(3) . . . . ?
S1B C4 C5 C6 177.9(4) . . . . ?
S1B C4 C9 C8 -178.5(4) . . . . ?
S1B C4 C9 C3B -2.8(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mw488_2_a
_database_code_depnum_ccdc_archive 'CCDC 2068878'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H14 O S'
_chemical_formula_sum            'C23 H14 O S'
_chemical_formula_weight         338.40
_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'
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                   13.183(11)
_cell_length_b                   11.272(8)
_cell_length_c                   11.792(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.60(3)
_cell_angle_gamma                90
_cell_volume                     1737(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5197
_cell_measurement_temperature    400
_cell_measurement_theta_max      25.191
_cell_measurement_theta_min      2.386
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.8778.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.111
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18361
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.905
_diffrn_reflns_theta_min         1.558
_diffrn_ambient_temperature      400
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1864
_reflns_number_total             3576
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_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
S1 S 0.76499(5) 0.60690(6) 0.39800(5) 0.0725(2) Uani 1 1 d . . . . .
O1 O 0.91938(15) 0.47804(17) 0.16752(15) 0.1032(7) Uani 1 1 d . . . . .
C1 C 0.76966(17) 0.6700(2) 0.17312(18) 0.0653(6) Uani 1 1 d . . . . .
H1 H 0.795930 0.656015 0.104933 0.078 Uiso 1 1 calc R U . . .
C2 C 0.80483(16) 0.60047(19) 0.26134(18) 0.0599(6) Uani 1 1 d . . . . .
C3 C 0.87950(18) 0.4997(2) 0.2526(2) 0.0668(6) Uani 1 1 d . . . . .
C4 C 0.89508(17) 0.4330(2) 0.36096(18) 0.0608(6) Uani 1 1 d . . . . .
C5 C 0.95726(19) 0.3331(2) 0.3858(2) 0.0794(7) Uani 1 1 d . . . . .
H5 H 0.994997 0.302468 0.331277 0.095 Uiso 1 1 calc R U . . .
C6 C 0.9619(2) 0.2808(2) 0.4918(3) 0.0895(8) Uani 1 1 d . . . . .
H6 H 1.002446 0.214047 0.509115 0.107 Uiso 1 1 calc R U . . .
C7 C 0.9061(2) 0.3276(3) 0.5723(2) 0.0903(8) Uani 1 1 d . . . . .
H7 H 0.909652 0.291121 0.643468 0.108 Uiso 1 1 calc R U . . .
C8 C 0.8449(2) 0.4275(2) 0.5503(2) 0.0806(7) Uani 1 1 d . . . . .
H8 H 0.808533 0.458447 0.605961 0.097 Uiso 1 1 calc R U . . .
C9 C 0.83947(17) 0.47982(19) 0.44287(19) 0.0614(6) Uani 1 1 d . . . . .
C10A C 0.71288(17) 0.86887(19) 0.24236(17) 0.0584(6) Uani 1 1 d . . . . .
C10 C 0.69301(17) 0.76747(19) 0.17160(17) 0.0566(6) Uani 1 1 d . . . . .
C11 C 0.54227(19) 0.9469(2) 0.17026(19) 0.0678(6) Uani 1 1 d . . . . .
H11 H 0.492231 1.004789 0.171793 0.081 Uiso 1 1 calc R U . . .
C11A C 0.63576(18) 0.95998(19) 0.24077(18) 0.0612(6) Uani 1 1 d . . . . .
C12A C 0.59940(17) 0.75858(19) 0.09652(17) 0.0569(6) Uani 1 1 d . . . . .
C12 C 0.5770(2) 0.6626(2) 0.01825(19) 0.0730(7) Uani 1 1 d . . . . .
H12 H 0.625087 0.602731 0.015192 0.088 Uiso 1 1 calc R U . . .
C13 C 0.4858(2) 0.6573(2) -0.0525(2) 0.0822(8) Uani 1 1 d . . . . .
H13 H 0.473559 0.594316 -0.103409 0.099 Uiso 1 1 calc R U . . .
C14 C 0.4097(2) 0.7459(3) -0.0498(2) 0.0832(7) Uani 1 1 d . . . . .
H14 H 0.348206 0.740497 -0.098244 0.100 Uiso 1 1 calc R U . . .
C15 C 0.42696(19) 0.8379(2) 0.0231(2) 0.0762(7) Uani 1 1 d . . . . .
H15 H 0.376423 0.895096 0.025321 0.091 Uiso 1 1 calc R U . . .
C15A C 0.52192(18) 0.8493(2) 0.09764(18) 0.0601(6) Uani 1 1 d . . . . .
C16 C 0.6574(2) 1.0635(2) 0.3103(2) 0.0780(7) Uani 1 1 d . . . . .
H16 H 0.607889 1.122206 0.310686 0.094 Uiso 1 1 calc R U . . .
C17 C 0.7498(2) 1.0770(3) 0.3760(2) 0.0876(8) Uani 1 1 d . . . . .
H17 H 0.762657 1.144405 0.421023 0.105 Uiso 1 1 calc R U . . .
C18 C 0.8264(2) 0.9890(2) 0.3760(2) 0.0824(8) Uani 1 1 d . . . . .
H18 H 0.889485 1.000007 0.420352 0.099 Uiso 1 1 calc R U . . .
C19 C 0.80924(19) 0.8890(2) 0.31250(18) 0.0698(6) Uani 1 1 d . . . . .
H19 H 0.860707 0.832345 0.314279 0.084 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 C2 1.761(2) . ?
S1 C9 1.777(2) . ?
O1 C3 1.218(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.336(3) . ?
C1 C10 1.491(3) . ?
C2 C3 1.516(3) . ?
C3 C4 1.473(3) . ?
C4 C5 1.401(3) . ?
C4 C9 1.391(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(3) . ?
C10A C10 1.419(3) . ?
C10A C11A 1.443(3) . ?
C10A C19 1.439(3) . ?
C10 C12A 1.424(3) . ?
C11 H11 0.9300 . ?
C11 C11A 1.400(3) . ?
C11 C15A 1.398(3) . ?
C11A C16 1.434(3) . ?
C12A C12 1.427(3) . ?
C12A C15A 1.447(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.418(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.347(3) . ?
C15 H15 0.9300 . ?
C15 C15A 1.437(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.362(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.414(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.356(3) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C9 91.11(11) . . ?
C2 C1 H1 116.3 . . ?
C2 C1 C10 127.3(2) . . ?
C10 C1 H1 116.3 . . ?
C1 C2 S1 125.01(18) . . ?
C1 C2 C3 123.3(2) . . ?
C3 C2 S1 111.58(16) . . ?
O1 C3 C2 124.1(2) . . ?
O1 C3 C4 125.9(2) . . ?
C4 C3 C2 109.9(2) . . ?
C5 C4 C3 127.0(2) . . ?
C9 C4 C3 112.5(2) . . ?
C9 C4 C5 120.5(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.8(3) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.0(3) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 120.9 . . ?
C7 C8 C9 118.2(3) . . ?
C9 C8 H8 120.9 . . ?
C4 C9 S1 114.83(17) . . ?
C8 C9 S1 125.0(2) . . ?
C8 C9 C4 120.2(2) . . ?
C10 C10A C11A 119.4(2) . . ?
C10 C10A C19 123.0(2) . . ?
C19 C10A C11A 117.5(2) . . ?
C10A C10 C1 121.0(2) . . ?
C10A C10 C12A 120.0(2) . . ?
C12A C10 C1 119.1(2) . . ?
C11A C11 H11 119.0 . . ?
C15A C11 H11 119.0 . . ?
C15A C11 C11A 122.0(2) . . ?
C11 C11A C10A 119.7(2) . . ?
C11 C11A C16 121.3(2) . . ?
C16 C11A C10A 119.0(2) . . ?
C10 C12A C12 122.9(2) . . ?
C10 C12A C15A 120.0(2) . . ?
C12 C12A C15A 117.1(2) . . ?
C12A C12 H12 119.5 . . ?
C13 C12 C12A 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C15A 121.3(2) . . ?
C15A C15 H15 119.4 . . ?
C11 C15A C12A 118.9(2) . . ?
C11 C15A C15 121.7(2) . . ?
C15 C15A C12A 119.4(2) . . ?
C11A C16 H16 119.6 . . ?
C17 C16 C11A 120.7(2) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C10A C19 H19 119.4 . . ?
C18 C19 C10A 121.2(2) . . ?
C18 C19 H19 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C2 C3 O1 -178.7(2) . . . . ?
S1 C2 C3 C4 1.7(2) . . . . ?
O1 C3 C4 C5 -0.5(4) . . . . ?
O1 C3 C4 C9 179.6(2) . . . . ?
C1 C2 C3 O1 5.2(4) . . . . ?
C1 C2 C3 C4 -174.3(2) . . . . ?
C1 C10 C12A C12 -2.9(3) . . . . ?
C1 C10 C12A C15A 177.00(18) . . . . ?
C2 S1 C9 C4 1.17(18) . . . . ?
C2 S1 C9 C8 -178.9(2) . . . . ?
C2 C1 C10 C10A 62.4(3) . . . . ?
C2 C1 C10 C12A -118.5(3) . . . . ?
C2 C3 C4 C5 179.1(2) . . . . ?
C2 C3 C4 C9 -0.9(3) . . . . ?
C3 C4 C5 C6 -179.2(2) . . . . ?
C3 C4 C9 S1 -0.3(3) . . . . ?
C3 C4 C9 C8 179.8(2) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C4 C9 S1 179.72(17) . . . . ?
C5 C4 C9 C8 -0.2(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C9 0.9(4) . . . . ?
C7 C8 C9 S1 179.51(19) . . . . ?
C7 C8 C9 C4 -0.6(3) . . . . ?
C9 S1 C2 C1 174.4(2) . . . . ?
C9 S1 C2 C3 -1.64(17) . . . . ?
C9 C4 C5 C6 0.7(4) . . . . ?
C10A C10 C12A C12 176.18(18) . . . . ?
C10A C10 C12A C15A -3.9(3) . . . . ?
C10A C11A C16 C17 0.9(3) . . . . ?
C10 C1 C2 S1 1.6(4) . . . . ?
C10 C1 C2 C3 177.1(2) . . . . ?
C10 C10A C11A C11 0.5(3) . . . . ?
C10 C10A C11A C16 -178.44(19) . . . . ?
C10 C10A C19 C18 177.8(2) . . . . ?
C10 C12A C12 C13 179.9(2) . . . . ?
C10 C12A C15A C11 2.3(3) . . . . ?
C10 C12A C15A C15 -178.69(18) . . . . ?
C11 C11A C16 C17 -178.0(2) . . . . ?
C11A C10A C10 C1 -178.38(18) . . . . ?
C11A C10A C10 C12A 2.5(3) . . . . ?
C11A C10A C19 C18 1.0(3) . . . . ?
C11A C11 C15A C12A 0.8(3) . . . . ?
C11A C11 C15A C15 -178.2(2) . . . . ?
C11A C16 C17 C18 0.4(4) . . . . ?
C12A C12 C13 C14 -0.8(4) . . . . ?
C12 C12A C15A C11 -177.82(18) . . . . ?
C12 C12A C15A C15 1.2(3) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C15A 0.9(4) . . . . ?
C14 C15 C15A C11 177.3(2) . . . . ?
C14 C15 C15A C12A -1.7(3) . . . . ?
C15A C11 C11A C10A -2.1(3) . . . . ?
C15A C11 C11A C16 176.72(19) . . . . ?
C15A C12A C12 C13 0.0(3) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
C17 C18 C19 C10A 0.3(4) . . . . ?
C19 C10A C10 C1 4.9(3) . . . . ?
C19 C10A C10 C12A -174.20(18) . . . . ?
C19 C10A C11A C11 177.37(19) . . . . ?
C19 C10A C11A C16 -1.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mw469_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2068880'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H14 O S'
_chemical_formula_sum            'C23 H14 O S'
_chemical_formula_weight         338.40
_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'
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                   10.351(12)
_cell_length_b                   13.886(17)
_cell_length_c                   11.185(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.99(3)
_cell_angle_gamma                90
_cell_volume                     1567(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5476
_cell_measurement_temperature    133
_cell_measurement_theta_max      26.370
_cell_measurement_theta_min      2.361
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0942 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.8999.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.254
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17973
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.563
_diffrn_reflns_theta_min         2.019
_diffrn_ambient_temperature      133
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.99
_diffrn_source_power             0.0495
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2758
_reflns_number_total             3260
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3260
_refine_ls_number_restraints     485
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²+0.8439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0825
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C2-C3B
 1.492 with sigma of 0.02
 S2B-C2
 1.75 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(S2B)=Sof(O1B)=Sof(C3B)=1-FVAR(1)
 Sof(S1A)=Sof(O1A)=Sof(C3A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C7(H7), C6(H6), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_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
C1 C 0.68383(15) 0.42544(11) 0.50417(14) 0.0185(3) Uani 1 1 d . U . . .
H1 H 0.646452 0.429540 0.418596 0.022 Uiso 1 1 calc R U . . .
C2 C 0.72730(15) 0.33858(11) 0.54404(14) 0.0189(3) Uani 1 1 d D U . . .
C9 C 0.85009(15) 0.20935(11) 0.66354(14) 0.0191(3) Uani 1 1 d . U . . .
C8 C 0.93007(16) 0.15855(12) 0.75782(14) 0.0228(3) Uani 1 1 d . U . . .
H8 H 0.961252 0.187519 0.835928 0.027 Uiso 1 1 calc R U . . .
C7 C 0.96406(16) 0.06506(12) 0.73690(15) 0.0229(3) Uani 1 1 d . U . . .
H7 H 1.019843 0.029272 0.800557 0.028 Uiso 1 1 calc R U . . .
C6 C 0.91678(16) 0.02344(11) 0.62304(15) 0.0225(3) Uani 1 1 d . U . . .
H6 H 0.941302 -0.040900 0.609556 0.027 Uiso 1 1 calc R U . . .
C5 C 0.83528(16) 0.07278(12) 0.52898(15) 0.0220(3) Uani 1 1 d . U . . .
H5 H 0.802282 0.043204 0.451537 0.026 Uiso 1 1 calc R U . . .
C4 C 0.80279(15) 0.16681(11) 0.55055(14) 0.0195(3) Uani 1 1 d . U . . .
C10 C 0.68467(15) 0.51604(11) 0.57197(13) 0.0172(3) Uani 1 1 d . U . . .
C10A C 0.61817(15) 0.52574(11) 0.66761(13) 0.0175(3) Uani 1 1 d . U . . .
C11 C 0.66242(15) 0.69784(11) 0.67335(14) 0.0212(3) Uani 1 1 d . U . . .
H11 H 0.654078 0.759622 0.707308 0.025 Uiso 1 1 calc R U . . .
C11A C 0.60666(15) 0.61882(11) 0.71821(14) 0.0190(3) Uani 1 1 d . U . . .
C12 C 0.81346(16) 0.59024(12) 0.43520(14) 0.0226(3) Uani 1 1 d . U . . .
H12 H 0.822977 0.529393 0.399307 0.027 Uiso 1 1 calc R U . . .
C12A C 0.74130(15) 0.59693(11) 0.52852(13) 0.0182(3) Uani 1 1 d . U . . .
C13 C 0.86911(16) 0.66917(13) 0.39630(15) 0.0267(4) Uani 1 1 d . U . . .
H13 H 0.917377 0.662867 0.333825 0.032 Uiso 1 1 calc R U . . .
C14 C 0.85630(16) 0.76070(12) 0.44742(15) 0.0271(4) Uani 1 1 d . U . . .
H14 H 0.895276 0.815598 0.419001 0.032 Uiso 1 1 calc R U . . .
C15 C 0.78885(16) 0.76999(12) 0.53635(15) 0.0243(4) Uani 1 1 d . U . . .
H15 H 0.780528 0.831799 0.570237 0.029 Uiso 1 1 calc R U . . .
C15A C 0.72973(15) 0.68902(11) 0.58064(14) 0.0194(3) Uani 1 1 d . U . . .
C16 C 0.53560(16) 0.62975(12) 0.81181(14) 0.0237(4) Uani 1 1 d . U . . .
H16 H 0.528421 0.691697 0.845780 0.028 Uiso 1 1 calc R U . . .
C17 C 0.47811(17) 0.55361(12) 0.85329(15) 0.0260(4) Uani 1 1 d . U . . .
H17 H 0.430289 0.561993 0.915762 0.031 Uiso 1 1 calc R U . . .
C18 C 0.48903(16) 0.46142(12) 0.80381(15) 0.0248(4) Uani 1 1 d . U . . .
H18 H 0.448933 0.407876 0.834035 0.030 Uiso 1 1 calc R U . . .
C19 C 0.55528(16) 0.44788(11) 0.71446(14) 0.0213(3) Uani 1 1 d . U . . .
H19 H 0.560095 0.385068 0.682096 0.026 Uiso 1 1 calc R U . . .
S1A S 0.70150(7) 0.23985(4) 0.44053(7) 0.0178(3) Uani 0.838(4) 1 d . U P A 1
O1A O 0.8461(2) 0.36740(16) 0.74899(19) 0.0203(4) Uani 0.838(4) 1 d . U P A 1
C3A C 0.8099(4) 0.3099(3) 0.6620(3) 0.0177(7) Uani 0.838(4) 1 d . U P A 1
S2B S 0.8235(5) 0.3299(4) 0.7100(5) 0.0340(18) Uani 0.162(4) 1 d D U P A 2
O1B O 0.6673(15) 0.2443(9) 0.3778(16) 0.077(5) Uani 0.162(4) 1 d . U P A 2
C3B C 0.7325(19) 0.2511(11) 0.4850(17) 0.034(3) Uani 0.162(4) 1 d D U P A 2


_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 H1 0.9500 . ?
C1 C2 1.329(2) . ?
C1 C10 1.468(2) . ?
C2 S1A 1.775(2) . ?
C2 C3A 1.457(4) . ?
C2 S2B 1.902(6) . ?
C2 C3B 1.389(14) . ?
C9 C8 1.379(2) . ?
C9 C4 1.381(2) . ?
C9 C3A 1.456(4) . ?
C9 S2B 1.793(6) . ?
C8 H8 0.9500 . ?
C8 C7 1.379(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.374(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.383(3) . ?
C4 S1A 1.750(2) . ?
C4 C3B 1.482(16) . ?
C10 C10A 1.403(2) . ?
C10 C12A 1.403(2) . ?
C10A C11A 1.427(3) . ?
C10A C19 1.421(2) . ?
C11 H11 0.9500 . ?
C11 C11A 1.385(2) . ?
C11 C15A 1.379(3) . ?
C11A C16 1.416(2) . ?
C12 H12 0.9500 . ?
C12 C12A 1.417(2) . ?
C12 C13 1.355(3) . ?
C12A C15A 1.421(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.412(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.344(3) . ?
C15 H15 0.9500 . ?
C15 C15A 1.421(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.346(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.409(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.346(2) . ?
C19 H19 0.9500 . ?
O1A C3A 1.250(4) . ?
O1B C3B 1.24(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
C2 C1 H1 115.0 . . ?
C2 C1 C10 129.96(15) . . ?
C10 C1 H1 115.0 . . ?
C1 C2 S1A 119.47(14) . . ?
C1 C2 C3A 129.62(19) . . ?
C1 C2 S2B 116.6(2) . . ?
C1 C2 C3B 132.9(8) . . ?
C3A C2 S1A 110.54(18) . . ?
C3B C2 S2B 109.9(8) . . ?
C8 C9 C4 120.61(16) . . ?
C8 C9 C3A 128.35(18) . . ?
C8 C9 S2B 111.2(2) . . ?
C4 C9 C3A 110.96(18) . . ?
C4 C9 S2B 128.2(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 C9 118.95(16) . . ?
C7 C8 H8 120.5 . . ?
C8 C7 H7 120.0 . . ?
C8 C7 C6 119.90(15) . . ?
C6 C7 H7 120.0 . . ?
C7 C6 H6 119.2 . . ?
C5 C6 C7 121.70(16) . . ?
C5 C6 H6 119.2 . . ?
C6 C5 H5 121.0 . . ?
C6 C5 C4 117.94(16) . . ?
C4 C5 H5 121.0 . . ?
C9 C4 C5 120.89(15) . . ?
C9 C4 S1A 115.38(14) . . ?
C9 C4 C3B 98.5(6) . . ?
C5 C4 S1A 123.73(13) . . ?
C5 C4 C3B 140.4(6) . . ?
C10A C10 C1 121.97(14) . . ?
C10A C10 C12A 120.14(15) . . ?
C12A C10 C1 117.48(15) . . ?
C10 C10A C11A 119.25(14) . . ?
C10 C10A C19 123.51(15) . . ?
C19 C10A C11A 117.18(15) . . ?
C11A C11 H11 119.2 . . ?
C15A C11 H11 119.2 . . ?
C15A C11 C11A 121.62(15) . . ?
C11 C11A C10A 119.68(16) . . ?
C11 C11A C16 120.72(15) . . ?
C16 C11A C10A 119.59(14) . . ?
C12A C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C13 C12 C12A 121.09(16) . . ?
C10 C12A C12 122.22(15) . . ?
C10 C12A C15A 119.85(16) . . ?
C12 C12A C15A 117.92(14) . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.84(17) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.86(16) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C15A 121.21(16) . . ?
C15A C15 H15 119.4 . . ?
C11 C15A C12A 119.46(14) . . ?
C11 C15A C15 121.46(15) . . ?
C15 C15A C12A 119.08(16) . . ?
C11A C16 H16 119.5 . . ?
C17 C16 C11A 120.93(16) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.83(17) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.17(16) . . ?
C19 C18 H18 119.4 . . ?
C10A C19 H19 119.4 . . ?
C18 C19 C10A 121.29(16) . . ?
C18 C19 H19 119.4 . . ?
C4 S1A C2 90.60(11) . . ?
C9 C3A C2 112.4(2) . . ?
O1A C3A C2 122.8(3) . . ?
O1A C3A C9 124.7(3) . . ?
C9 S2B C2 81.8(3) . . ?
C2 C3B C4 121.5(12) . . ?
O1B C3B C2 117.1(14) . . ?
O1B C3B C4 121.2(12) . . ?

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
C1 C2 S1A C4 171.55(13) . . . . ?
C1 C2 C3A C9 -172.28(18) . . . . ?
C1 C2 C3A O1A 4.7(5) . . . . ?
C1 C2 C3B C4 172.0(7) . . . . ?
C1 C2 C3B O1B -13(3) . . . . ?
C1 C10 C10A C11A -171.13(14) . . . . ?
C1 C10 C10A C19 5.9(2) . . . . ?
C1 C10 C12A C12 -9.6(2) . . . . ?
C1 C10 C12A C15A 171.92(13) . . . . ?
C2 C1 C10 C10A -60.4(2) . . . . ?
C2 C1 C10 C12A 127.08(19) . . . . ?
C9 C8 C7 C6 -0.7(2) . . . . ?
C9 C4 S1A C2 3.39(13) . . . . ?
C9 C4 C3B C2 -2.0(16) . . . . ?
C9 C4 C3B O1B -176.3(19) . . . . ?
C8 C9 C4 C5 -0.5(2) . . . . ?
C8 C9 C4 S1A 179.49(12) . . . . ?
C8 C9 C4 C3B -177.0(8) . . . . ?
C8 C9 C3A C2 178.46(18) . . . . ?
C8 C9 C3A O1A 1.6(5) . . . . ?
C8 C9 S2B C2 177.73(14) . . . . ?
C8 C7 C6 C5 -0.4(2) . . . . ?
C7 C6 C5 C4 1.0(2) . . . . ?
C6 C5 C4 C9 -0.5(2) . . . . ?
C6 C5 C4 S1A 179.46(12) . . . . ?
C6 C5 C4 C3B 173.9(12) . . . . ?
C5 C4 S1A C2 -176.58(14) . . . . ?
C5 C4 C3B C2 -177.2(6) . . . . ?
C5 C4 C3B O1B 9(3) . . . . ?
C4 C9 C8 C7 1.1(2) . . . . ?
C4 C9 C3A C2 1.9(3) . . . . ?
C4 C9 C3A O1A -175.0(3) . . . . ?
C4 C9 S2B C2 -1.4(3) . . . . ?
C10 C1 C2 S1A 175.42(13) . . . . ?
C10 C1 C2 C3A -12.3(3) . . . . ?
C10 C1 C2 S2B -7.9(3) . . . . ?
C10 C1 C2 C3B -178.1(11) . . . . ?
C10 C10A C11A C11 -0.7(2) . . . . ?
C10 C10A C11A C16 177.76(14) . . . . ?
C10 C10A C19 C18 -177.86(15) . . . . ?
C10 C12A C15A C11 -0.2(2) . . . . ?
C10 C12A C15A C15 179.37(14) . . . . ?
C10A C10 C12A C12 177.70(14) . . . . ?
C10A C10 C12A C15A -0.8(2) . . . . ?
C10A C11A C16 C17 -0.4(2) . . . . ?
C11 C11A C16 C17 178.13(16) . . . . ?
C11A C10A C19 C18 -0.8(2) . . . . ?
C11A C11 C15A C12A 0.7(2) . . . . ?
C11A C11 C15A C15 -178.86(15) . . . . ?
C11A C16 C17 C18 0.4(3) . . . . ?
C12 C12A C15A C11 -178.73(14) . . . . ?
C12 C12A C15A C15 0.8(2) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C12A C10 C10A C11A 1.2(2) . . . . ?
C12A C10 C10A C19 178.28(14) . . . . ?
C12A C12 C13 C14 -0.3(2) . . . . ?
C13 C12 C12A C10 -178.86(15) . . . . ?
C13 C12 C12A C15A -0.4(2) . . . . ?
C13 C14 C15 C15A 0.1(2) . . . . ?
C14 C15 C15A C11 178.84(15) . . . . ?
C14 C15 C15A C12A -0.7(2) . . . . ?
C15A C11 C11A C10A -0.2(2) . . . . ?
C15A C11 C11A C16 -178.71(14) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 C10A 0.8(2) . . . . ?
C19 C10A C11A C11 -177.98(14) . . . . ?
C19 C10A C11A C16 0.5(2) . . . . ?
S1A C2 C3A C9 0.5(3) . . . . ?
S1A C2 C3A O1A 177.5(3) . . . . ?
C3A C2 S1A C4 -2.10(19) . . . . ?
C3A C9 C8 C7 -175.1(2) . . . . ?
C3A C9 C4 C5 176.3(2) . . . . ?
C3A C9 C4 S1A -3.6(2) . . . . ?
S2B C2 C3B C4 1.3(18) . . . . ?
S2B C2 C3B O1B 175.8(17) . . . . ?
S2B C9 C8 C7 -178.1(2) . . . . ?
S2B C9 C4 C5 178.6(3) . . . . ?
S2B C9 C4 C3B 2.1(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mw458_a
_database_code_depnum_ccdc_archive 'CCDC 2068879'
loop_
_audit_author_name
_audit_author_address
'Duane Hean'
;University of British Columbia
Canada
;
_audit_update_record             
;
2021-03-08 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H14 O S'
_chemical_formula_sum            'C23 H14 O S'
_chemical_formula_weight         338.40
_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'
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                   10.4430(4)
_cell_length_b                   13.9757(5)
_cell_length_c                   11.2410(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.9160(10)
_cell_angle_gamma                90
_cell_volume                     1599.09(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.921
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0482 before and 0.0433 after correction.
The Ratio of minimum to maximum transmission is 0.9471.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.254
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_min         2.001
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4060
_reflns_number_total             4866
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4866
_refine_ls_number_restraints     486
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.6542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C3B-O1B
 1.236 with sigma of 0.02
 C2-C3B
 1.492 with sigma of 0.02
 S1B-C2
 1.8 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(S1B)=Sof(O1B)=Sof(C3B)=1-FVAR(1)
 Sof(S1A)=Sof(O1A)=Sof(C3A)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_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
C1 C 0.31667(11) 0.42585(8) 0.49763(10) 0.0143(2) Uani 1 1 d . U . . .
H1 H 0.353481 0.430427 0.582726 0.017 Uiso 1 1 calc R U . . .
C2 C 0.27361(11) 0.33809(8) 0.45786(10) 0.0141(2) Uani 1 1 d D U . . .
C4 C 0.19778(11) 0.16584(8) 0.45103(10) 0.0143(2) Uani 1 1 d . U . . .
C5 C 0.16445(11) 0.07142(8) 0.47156(11) 0.0169(2) Uani 1 1 d . U . . .
H5 H 0.196919 0.041401 0.548195 0.020 Uiso 1 1 calc R U . . .
C6 C 0.08233(11) 0.02274(8) 0.37642(11) 0.0174(2) Uani 1 1 d . U . . .
H6 H 0.057361 -0.041180 0.389019 0.021 Uiso 1 1 calc R U . . .
C7 C 0.03556(12) 0.06567(8) 0.26252(11) 0.0185(2) Uani 1 1 d . U . . .
H7 H -0.019911 0.030655 0.198809 0.022 Uiso 1 1 calc R U . . .
C8 C 0.06996(11) 0.15934(8) 0.24227(10) 0.0169(2) Uani 1 1 d . U . . .
H8 H 0.039104 0.188691 0.164940 0.020 Uiso 1 1 calc R U . . .
C9 C 0.15072(11) 0.20951(8) 0.33769(10) 0.0138(2) Uani 1 1 d . U . . .
C10A C 0.38173(11) 0.52570(8) 0.33272(10) 0.0137(2) Uani 1 1 d . U . . .
C10 C 0.31517(11) 0.51590(8) 0.42874(10) 0.0135(2) Uani 1 1 d . U . . .
C11 C 0.33719(11) 0.69831(8) 0.32662(11) 0.0170(2) Uani 1 1 d . U . . .
H11 H 0.345318 0.759652 0.292639 0.020 Uiso 1 1 calc R U . . .
C11A C 0.39306(11) 0.61909(8) 0.28191(10) 0.0152(2) Uani 1 1 d . U . . .
C12A C 0.25840(11) 0.59710(8) 0.47214(10) 0.0145(2) Uani 1 1 d . U . . .
C12 C 0.18597(11) 0.59014(9) 0.56597(11) 0.0182(2) Uani 1 1 d . U . . .
H12 H 0.176670 0.529674 0.601719 0.022 Uiso 1 1 calc R U . . .
C13 C 0.12994(12) 0.66935(9) 0.60490(11) 0.0216(2) Uani 1 1 d . U . . .
H13 H 0.082017 0.663066 0.667047 0.026 Uiso 1 1 calc R U . . .
C14 C 0.14258(12) 0.76115(9) 0.55341(12) 0.0221(3) Uani 1 1 d . U . . .
H14 H 0.103564 0.815621 0.581476 0.027 Uiso 1 1 calc R U . . .
C15A C 0.26989(11) 0.68942(8) 0.41982(10) 0.0158(2) Uani 1 1 d . U . . .
C15 C 0.21058(12) 0.77061(9) 0.46403(11) 0.0202(2) Uani 1 1 d . U . . .
H15 H 0.218918 0.832027 0.430347 0.024 Uiso 1 1 calc R U . . .
C16 C 0.46431(12) 0.63008(9) 0.18809(11) 0.0191(2) Uani 1 1 d . U . . .
H16 H 0.471441 0.691677 0.154416 0.023 Uiso 1 1 calc R U . . .
C17 C 0.52219(12) 0.55372(9) 0.14611(11) 0.0207(2) Uani 1 1 d . U . . .
H17 H 0.569457 0.562128 0.083811 0.025 Uiso 1 1 calc R U . . .
C18 C 0.51150(12) 0.46125(9) 0.19605(11) 0.0199(2) Uani 1 1 d . U . . .
H18 H 0.551781 0.408147 0.166305 0.024 Uiso 1 1 calc R U . . .
C19 C 0.44447(11) 0.44744(8) 0.28589(11) 0.0168(2) Uani 1 1 d . U . . .
H19 H 0.439285 0.385002 0.317891 0.020 Uiso 1 1 calc R U . . .
S1A S 0.29827(4) 0.23949(2) 0.56004(4) 0.01540(11) Uani 0.923(2) 1 d . U P A 1
O1A O 0.15480(11) 0.36749(9) 0.25131(11) 0.0172(2) Uani 0.923(2) 1 d . U P A 1
C3A C 0.19006(18) 0.31056(12) 0.33715(15) 0.0125(3) Uani 0.923(2) 1 d . U P A 1
S1B S 0.1786(7) 0.3313(6) 0.2919(7) 0.0310(19) Uani 0.077(2) 1 d D U P A 2
O1B O 0.329(2) 0.2433(12) 0.6279(17) 0.063(6) Uani 0.077(2) 1 d D U P A 2
C3B C 0.264(3) 0.2510(14) 0.5229(19) 0.033(5) Uani 0.077(2) 1 d D U P A 2


_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 H1 0.9500 . ?
C1 C2 1.3477(15) . ?
C1 C10 1.4760(15) . ?
C2 S1A 1.7754(11) . ?
C2 C3A 1.490(2) . ?
C2 S1B 1.909(8) . ?
C2 C3B 1.435(16) . ?
C4 C5 1.3970(15) . ?
C4 C9 1.3990(15) . ?
C4 S1A 1.7571(11) . ?
C4 C3B 1.51(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3900(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3994(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3897(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3960(15) . ?
C9 C3A 1.471(2) . ?
C9 S1B 1.821(8) . ?
C10A C10 1.4150(16) . ?
C10A C11A 1.4402(15) . ?
C10A C19 1.4341(15) . ?
C10 C12A 1.4165(15) . ?
C11 H11 0.9500 . ?
C11 C11A 1.3963(16) . ?
C11 C15A 1.3916(17) . ?
C11A C16 1.4285(17) . ?
C12A C12 1.4320(16) . ?
C12A C15A 1.4340(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3688(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.4257(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3602(19) . ?
C15A C15 1.4338(16) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.3617(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.4233(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.3649(17) . ?
C19 H19 0.9500 . ?
O1A C3A 1.2413(18) . ?
O1B C3B 1.227(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 H1 115.2 . . ?
C2 C1 C10 129.67(10) . . ?
C10 C1 H1 115.2 . . ?
C1 C2 S1A 120.15(8) . . ?
C1 C2 C3A 128.39(11) . . ?
C1 C2 S1B 115.5(2) . . ?
C1 C2 C3B 131.2(9) . . ?
C3A C2 S1A 111.06(9) . . ?
C3B C2 S1B 112.0(9) . . ?
C5 C4 C9 120.84(10) . . ?
C5 C4 S1A 124.76(9) . . ?
C5 C4 C3B 139.0(6) . . ?
C9 C4 S1A 114.39(8) . . ?
C9 C4 C3B 99.7(6) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 117.96(10) . . ?
C6 C5 H5 121.0 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.55(11) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.24(10) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.76(11) . . ?
C9 C8 H8 120.6 . . ?
C4 C9 C3A 112.39(11) . . ?
C4 C9 S1B 128.3(2) . . ?
C8 C9 C4 120.63(10) . . ?
C8 C9 C3A 126.88(11) . . ?
C8 C9 S1B 111.1(2) . . ?
C10 C10A C11A 119.21(10) . . ?
C10 C10A C19 123.29(10) . . ?
C19 C10A C11A 117.44(10) . . ?
C10A C10 C1 122.23(10) . . ?
C10A C10 C12A 120.00(10) . . ?
C12A C10 C1 117.30(10) . . ?
C11A C11 H11 119.3 . . ?
C15A C11 H11 119.3 . . ?
C15A C11 C11A 121.47(10) . . ?
C11 C11A C10A 119.87(10) . . ?
C11 C11A C16 120.60(10) . . ?
C16 C11A C10A 119.52(10) . . ?
C10 C12A C12 122.00(10) . . ?
C10 C12A C15A 119.98(10) . . ?
C12 C12A C15A 118.00(10) . . ?
C12A C12 H12 119.5 . . ?
C13 C12 C12A 120.96(11) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.86(12) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.89(11) . . ?
C15 C14 H14 120.1 . . ?
C11 C15A C12A 119.46(10) . . ?
C11 C15A C15 121.35(11) . . ?
C15 C15A C12A 119.19(11) . . ?
C14 C15 C15A 121.09(12) . . ?
C14 C15 H15 119.5 . . ?
C15A C15 H15 119.5 . . ?
C11A C16 H16 119.5 . . ?
C17 C16 C11A 121.09(11) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.66(11) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.24(11) . . ?
C19 C18 H18 119.4 . . ?
C10A C19 H19 119.5 . . ?
C18 C19 C10A 121.04(11) . . ?
C18 C19 H19 119.5 . . ?
C4 S1A C2 91.48(5) . . ?
C9 C3A C2 110.56(12) . . ?
O1A C3A C2 123.63(16) . . ?
O1A C3A C9 125.73(16) . . ?
C9 S1B C2 81.4(4) . . ?
C2 C3B C4 118.1(13) . . ?
O1B C3B C2 118.5(17) . . ?
O1B C3B C4 122.1(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
C1 C2 S1A C4 171.27(10) . . . . ?
C1 C2 C3A C9 -172.05(12) . . . . ?
C1 C2 C3A O1A 4.9(3) . . . . ?
C1 C2 C3B C4 174.1(9) . . . . ?
C1 C2 C3B O1B -19(4) . . . . ?
C1 C10 C12A C12 -10.10(15) . . . . ?
C1 C10 C12A C15A 171.43(10) . . . . ?
C2 C1 C10 C10A -60.46(17) . . . . ?
C2 C1 C10 C12A 127.48(13) . . . . ?
C4 C5 C6 C7 1.03(18) . . . . ?
C4 C9 C3A C2 1.74(17) . . . . ?
C4 C9 C3A O1A -175.09(17) . . . . ?
C4 C9 S1B C2 -1.6(4) . . . . ?
C5 C4 C9 C8 -0.40(17) . . . . ?
C5 C4 C9 C3A 176.37(12) . . . . ?
C5 C4 C9 S1B 178.7(3) . . . . ?
C5 C4 S1A C2 -176.57(10) . . . . ?
C5 C4 C3B C2 -178.9(7) . . . . ?
C5 C4 C3B O1B 15(4) . . . . ?
C5 C6 C7 C8 -0.49(18) . . . . ?
C6 C7 C8 C9 -0.52(18) . . . . ?
C7 C8 C9 C4 0.95(17) . . . . ?
C7 C8 C9 C3A -175.31(13) . . . . ?
C7 C8 C9 S1B -178.3(3) . . . . ?
C8 C9 C3A C2 178.26(12) . . . . ?
C8 C9 C3A O1A 1.4(3) . . . . ?
C8 C9 S1B C2 177.52(13) . . . . ?
C9 C4 C5 C6 -0.59(17) . . . . ?
C9 C4 S1A C2 3.19(9) . . . . ?
C9 C4 C3B C2 -8(2) . . . . ?
C9 C4 C3B O1B -174(3) . . . . ?
C10A C10 C12A C12 177.65(10) . . . . ?
C10A C10 C12A C15A -0.82(15) . . . . ?
C10A C11A C16 C17 -0.24(17) . . . . ?
C10 C1 C2 S1A 175.54(9) . . . . ?
C10 C1 C2 C3A -12.4(2) . . . . ?
C10 C1 C2 S1B -8.0(3) . . . . ?
C10 C1 C2 C3B -174.3(16) . . . . ?
C10 C10A C11A C11 -0.78(16) . . . . ?
C10 C10A C11A C16 177.68(10) . . . . ?
C10 C10A C19 C18 -177.62(11) . . . . ?
C10 C12A C12 C13 -178.80(11) . . . . ?
C10 C12A C15A C11 -0.09(16) . . . . ?
C10 C12A C15A C15 179.34(10) . . . . ?
C11 C11A C16 C17 178.22(11) . . . . ?
C11 C15A C15 C14 178.62(11) . . . . ?
C11A C10A C10 C1 -170.61(10) . . . . ?
C11A C10A C10 C12A 1.24(15) . . . . ?
C11A C10A C19 C18 -0.40(16) . . . . ?
C11A C11 C15A C12A 0.56(16) . . . . ?
C11A C11 C15A C15 -178.86(11) . . . . ?
C11A C16 C17 C18 0.16(18) . . . . ?
C12A C12 C13 C14 -0.25(18) . . . . ?
C12A C15A C15 C14 -0.80(17) . . . . ?
C12 C12A C15A C11 -178.62(10) . . . . ?
C12 C12A C15A C15 0.81(15) . . . . ?
C12 C13 C14 C15 0.28(18) . . . . ?
C13 C14 C15 C15A 0.25(18) . . . . ?
C15A C11 C11A C10A -0.12(16) . . . . ?
C15A C11 C11A C16 -178.57(11) . . . . ?
C15A C12A C12 C13 -0.30(16) . . . . ?
C16 C17 C18 C19 -0.21(19) . . . . ?
C17 C18 C19 C10A 0.34(18) . . . . ?
C19 C10A C10 C1 6.56(16) . . . . ?
C19 C10A C10 C12A 178.41(10) . . . . ?
C19 C10A C11A C11 -178.12(10) . . . . ?
C19 C10A C11A C16 0.35(15) . . . . ?
S1A C2 C3A C9 0.58(16) . . . . ?
S1A C2 C3A O1A 177.49(16) . . . . ?
S1A C4 C5 C6 179.15(9) . . . . ?
S1A C4 C9 C8 179.83(9) . . . . ?
S1A C4 C9 C3A -3.40(14) . . . . ?
C3A C2 S1A C4 -2.05(11) . . . . ?
S1B C2 C3B C4 7(2) . . . . ?
S1B C2 C3B O1B 175(2) . . . . ?
C3B C4 C5 C6 169.4(17) . . . . ?
C3B C4 C9 C8 -173.7(11) . . . . ?
C3B C4 C9 S1B 5.3(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
