# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1955424'
loop_
_audit_author_name
_audit_author_address
'Bulat Gabidullin'
;University of Ottawa
Canada
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 O S'
_chemical_formula_weight         364.44

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.250(6)
_cell_length_b                   15.787(19)
_cell_length_c                   20.19(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1673(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    455
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      16.29

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2380
_exptl_absorpt_correction_T_max  0.7443
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8311
_diffrn_reflns_av_unetI/netI     0.1735
_diffrn_reflns_av_R_equivalents  0.2097
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.637
_diffrn_reflns_theta_max         18.902
_diffrn_reflns_theta_full        18.902
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1322
_reflns_number_gt                689
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.616
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0939P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 171 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1322
_refine_ls_number_parameters     245
_refine_ls_number_restraints     192
_refine_ls_R_factor_all          0.1696
_refine_ls_R_factor_gt           0.0807
_refine_ls_wR_factor_ref         0.2370
_refine_ls_wR_factor_gt          0.1747
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.010(4) 0.6026(16) 0.4458(11) 0.044(7) Uani 1 1 d . U . . .
C2 C -0.206(5) 0.6392(15) 0.4868(11) 0.060(8) Uani 1 1 d . U . . .
H2 H -0.2356 0.6986 0.4870 0.073 Uiso 1 1 calc R U . . .
C3 C -0.349(5) 0.5867(18) 0.5252(11) 0.059(7) Uani 1 1 d . U . . .
H3 H -0.4769 0.6097 0.5530 0.071 Uiso 1 1 calc R U . . .
C4 C -0.310(6) 0.5023(18) 0.5242(12) 0.066(8) Uani 1 1 d . U . . .
H4 H -0.4143 0.4670 0.5510 0.079 Uiso 1 1 calc R U . . .
C5 C -0.125(5) 0.4660(15) 0.4854(12) 0.058(7) Uani 1 1 d . U . . .
H5 H -0.1024 0.4063 0.4861 0.070 Uiso 1 1 calc R U . . .
C6 C 0.035(4) 0.5170(17) 0.4438(11) 0.045(7) Uani 1 1 d . U . . .
C7 C 0.242(4) 0.4802(16) 0.4024(10) 0.043(6) Uani 1 1 d . U . . .
C8 C 0.266(4) 0.3949(17) 0.4026(11) 0.052(7) Uani 1 1 d . U . . .
H8 H 0.1490 0.3626 0.4280 0.063 Uiso 1 1 calc R U . . .
C9 C 0.460(4) 0.3509(15) 0.3662(11) 0.045(7) Uani 1 1 d . U . . .
C10 C 0.624(5) 0.3987(16) 0.3257(10) 0.039(6) Uani 1 1 d . U . . .
C11 C 0.828(5) 0.3562(17) 0.2860(11) 0.047(7) Uani 1 1 d . U . . .
C12 C 0.971(4) 0.4102(17) 0.2403(10) 0.038(6) Uani 1 1 d . U . . .
C13 C 1.157(5) 0.3715(14) 0.1996(10) 0.054(7) Uani 1 1 d . U . . .
H13 H 1.1722 0.3116 0.1992 0.064 Uiso 1 1 calc R U . . .
C14 C 1.315(5) 0.4195(17) 0.1609(10) 0.050(7) Uani 1 1 d . U . . .
H14 H 1.4363 0.3921 0.1334 0.060 Uiso 1 1 calc R U . . .
C15 C 1.302(5) 0.5068(16) 0.1608(11) 0.060(7) Uani 1 1 d . U . . .
H15 H 1.4192 0.5395 0.1356 0.072 Uiso 1 1 calc R U . . .
C16 C 1.114(4) 0.5455(17) 0.1983(10) 0.055(7) Uani 1 1 d . U . . .
H16 H 1.0953 0.6053 0.1968 0.066 Uiso 1 1 calc R U . . .
C17 C 0.953(4) 0.4984(17) 0.2379(10) 0.040(6) Uani 1 1 d . U . . .
C18 C 0.748(4) 0.5390(15) 0.2785(10) 0.037(6) Uani 1 1 d . U . . .
C19 C 0.713(4) 0.6254(15) 0.2764(10) 0.046(7) Uani 1 1 d . U . . .
H19 H 0.8217 0.6588 0.2494 0.055 Uiso 1 1 calc R U . . .
C20 C 0.524(4) 0.6646(17) 0.3123(11) 0.052(7) Uani 1 1 d . U . . .
H20 H 0.4975 0.7239 0.3080 0.062 Uiso 1 1 calc R U . . .
C21 C 0.369(5) 0.6169(16) 0.3552(10) 0.042(6) Uani 1 1 d . U . . .
C22 C 0.393(4) 0.5278(15) 0.3595(10) 0.033(6) Uani 1 1 d . U . . .
C23 C 0.594(4) 0.4885(15) 0.3209(10) 0.037(6) Uani 1 1 d . U . . .
C24 C 0.472(4) 0.2566(15) 0.3750(10) 0.055(7) Uani 1 1 d . U . . .
H24A H 0.5108 0.2298 0.3318 0.066 Uiso 1 1 calc R U . . .
H24B H 0.3032 0.2357 0.3897 0.066 Uiso 1 1 calc R U . . .
C25 C 0.674(5) 0.2305(13) 0.4257(9) 0.073(8) Uani 1 1 d . U . . .
H25A H 0.8432 0.2470 0.4095 0.110 Uiso 1 1 calc R U . . .
H25B H 0.6688 0.1690 0.4321 0.110 Uiso 1 1 calc R U . . .
H25C H 0.6405 0.2589 0.4680 0.110 Uiso 1 1 calc R U . . .
O1 O 0.863(3) 0.2788(11) 0.2882(8) 0.068(6) Uani 1 1 d . U . . .
S1 S 0.1538(13) 0.6782(4) 0.3995(3) 0.070(2) Uani 1 1 d . 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
C1 C6 1.37(3) . ?
C1 C2 1.44(3) . ?
C1 S1 1.74(2) . ?
C2 C3 1.36(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.35(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.38(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.44(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.49(3) . ?
C7 C8 1.35(2) . ?
C7 C22 1.39(3) . ?
C8 C9 1.43(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.41(3) . ?
C9 C24 1.50(3) . ?
C10 C23 1.43(3) . ?
C10 C11 1.50(3) . ?
C11 O1 1.24(2) . ?
C11 C12 1.46(3) . ?
C12 C17 1.40(3) . ?
C12 C13 1.41(3) . ?
C13 C14 1.37(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.38(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.39(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.38(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.50(3) . ?
C18 C19 1.38(2) . ?
C18 C23 1.42(3) . ?
C19 C20 1.38(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.41(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.41(2) . ?
C21 S1 1.74(2) . ?
C22 C23 1.45(3) . ?
C24 C25 1.53(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122(2) . . ?
C6 C1 S1 125(2) . . ?
C2 C1 S1 113(2) . . ?
C3 C2 C1 118(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 121(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 122(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 121(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 116(2) . . ?
C1 C6 C7 122(2) . . ?
C5 C6 C7 122(2) . . ?
C8 C7 C22 119(2) . . ?
C8 C7 C6 117(2) . . ?
C22 C7 C6 124(2) . . ?
C7 C8 C9 123(2) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C10 C9 C8 118(2) . . ?
C10 C9 C24 125(2) . . ?
C8 C9 C24 117(2) . . ?
C9 C10 C23 120(2) . . ?
C9 C10 C11 121(2) . . ?
C23 C10 C11 119(2) . . ?
O1 C11 C12 122(3) . . ?
O1 C11 C10 122(3) . . ?
C12 C11 C10 116(2) . . ?
C17 C12 C13 117(2) . . ?
C17 C12 C11 125(2) . . ?
C13 C12 C11 118(2) . . ?
C14 C13 C12 121(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 122(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 118(2) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C17 C16 C15 121(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C12 121(2) . . ?
C16 C17 C18 122(2) . . ?
C12 C17 C18 117(2) . . ?
C19 C18 C23 120(2) . . ?
C19 C18 C17 120(2) . . ?
C23 C18 C17 120(2) . . ?
C20 C19 C18 122(2) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C19 C20 C21 120(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 121(2) . . ?
C20 C21 S1 113.2(19) . . ?
C22 C21 S1 126(2) . . ?
C7 C22 C21 122(2) . . ?
C7 C22 C23 121(2) . . ?
C21 C22 C23 117(2) . . ?
C18 C23 C10 122(2) . . ?
C18 C23 C22 120(2) . . ?
C10 C23 C22 118(2) . . ?
C9 C24 C25 112(2) . . ?
C9 C24 H24A 109.2 . . ?
C25 C24 H24A 109.2 . . ?
C9 C24 H24B 109.2 . . ?
C25 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C21 S1 C1 102.5(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1(3) . . . . ?
S1 C1 C2 C3 179.7(17) . . . . ?
C1 C2 C3 C4 -1(3) . . . . ?
C2 C3 C4 C5 1(4) . . . . ?
C3 C4 C5 C6 0(3) . . . . ?
C2 C1 C6 C5 0(3) . . . . ?
S1 C1 C6 C5 -179.0(15) . . . . ?
C2 C1 C6 C7 -178.7(18) . . . . ?
S1 C1 C6 C7 2(3) . . . . ?
C4 C5 C6 C1 0(3) . . . . ?
C4 C5 C6 C7 178.5(19) . . . . ?
C1 C6 C7 C8 -178(2) . . . . ?
C5 C6 C7 C8 3(3) . . . . ?
C1 C6 C7 C22 -4(3) . . . . ?
C5 C6 C7 C22 177.2(18) . . . . ?
C22 C7 C8 C9 7(3) . . . . ?
C6 C7 C8 C9 -178.7(18) . . . . ?
C7 C8 C9 C10 -3(3) . . . . ?
C7 C8 C9 C24 176(2) . . . . ?
C8 C9 C10 C23 -1(3) . . . . ?
C24 C9 C10 C23 180(2) . . . . ?
C8 C9 C10 C11 -179.5(19) . . . . ?
C24 C9 C10 C11 1(3) . . . . ?
C9 C10 C11 O1 -1(3) . . . . ?
C23 C10 C11 O1 -180(2) . . . . ?
C9 C10 C11 C12 174(2) . . . . ?
C23 C10 C11 C12 -5(3) . . . . ?
O1 C11 C12 C17 -176(2) . . . . ?
C10 C11 C12 C17 9(3) . . . . ?
O1 C11 C12 C13 -2(4) . . . . ?
C10 C11 C12 C13 -176.9(18) . . . . ?
C17 C12 C13 C14 1(3) . . . . ?
C11 C12 C13 C14 -173.2(19) . . . . ?
C12 C13 C14 C15 1(3) . . . . ?
C13 C14 C15 C16 -4(4) . . . . ?
C14 C15 C16 C17 4(3) . . . . ?
C15 C16 C17 C12 -1(3) . . . . ?
C15 C16 C17 C18 -179.6(19) . . . . ?
C13 C12 C17 C16 -1(3) . . . . ?
C11 C12 C17 C16 173(2) . . . . ?
C13 C12 C17 C18 177.1(17) . . . . ?
C11 C12 C17 C18 -9(3) . . . . ?
C16 C17 C18 C19 1(3) . . . . ?
C12 C17 C18 C19 -177.4(18) . . . . ?
C16 C17 C18 C23 -177.1(18) . . . . ?
C12 C17 C18 C23 5(3) . . . . ?
C23 C18 C19 C20 -3(3) . . . . ?
C17 C18 C19 C20 179.1(17) . . . . ?
C18 C19 C20 C21 3(3) . . . . ?
C19 C20 C21 C22 -4(3) . . . . ?
C19 C20 C21 S1 176.6(15) . . . . ?
C8 C7 C22 C21 177.3(18) . . . . ?
C6 C7 C22 C21 4(3) . . . . ?
C8 C7 C22 C23 -7(3) . . . . ?
C6 C7 C22 C23 179.4(16) . . . . ?
C20 C21 C22 C7 179.5(19) . . . . ?
S1 C21 C22 C7 -1(3) . . . . ?
C20 C21 C22 C23 4(3) . . . . ?
S1 C21 C22 C23 -177.0(15) . . . . ?
C19 C18 C23 C10 -179.2(19) . . . . ?
C17 C18 C23 C10 -1(3) . . . . ?
C19 C18 C23 C22 3(3) . . . . ?
C17 C18 C23 C22 -179.3(17) . . . . ?
C9 C10 C23 C18 -177.2(18) . . . . ?
C11 C10 C23 C18 2(3) . . . . ?
C9 C10 C23 C22 1(3) . . . . ?
C11 C10 C23 C22 179.6(17) . . . . ?
C7 C22 C23 C18 -178.9(19) . . . . ?
C21 C22 C23 C18 -3(3) . . . . ?
C7 C22 C23 C10 3(3) . . . . ?
C21 C22 C23 C10 178.9(19) . . . . ?
C10 C9 C24 C25 82(2) . . . . ?
C8 C9 C24 C25 -98(2) . . . . ?
C20 C21 S1 C1 178.9(15) . . . . ?
C22 C21 S1 C1 -1(2) . . . . ?
C6 C1 S1 C21 0(2) . . . . ?
C2 C1 S1 C21 -179.1(14) . . . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.073


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1955425'
loop_
_audit_author_name
_audit_author_address
'Bulat Gabidullin'
;University of Ottawa
Canada
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 O S'
_chemical_formula_weight         392.49

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.2279(10)
_cell_length_b                   19.702(4)
_cell_length_c                   18.914(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.686(6)
_cell_angle_gamma                90
_cell_volume                     1934.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1314
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.34

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.022
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6369
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11601
_diffrn_reflns_av_unetI/netI     0.2346
_diffrn_reflns_av_R_equivalents  0.1272
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.498
_diffrn_reflns_theta_max         24.129
_diffrn_reflns_theta_full        24.129
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3066
_reflns_number_gt                999
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0267P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3066
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2334
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.814
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.9042(3) 0.64554(8) 0.06954(8) 0.0707(5) Uani 1 1 d . . . . .
O1 O 0.5872(8) 0.74159(17) 0.44059(19) 0.0769(13) Uani 1 1 d . . . . .
C9 C 0.9092(10) 0.6660(2) 0.3564(3) 0.0357(14) Uani 1 1 d . . . . .
C22 C 0.8072(10) 0.6790(2) 0.2074(3) 0.0358(14) Uani 1 1 d . . . . .
C23 C 0.6583(9) 0.7165(2) 0.2533(3) 0.0297(13) Uani 1 1 d . . . . .
C18 C 0.4613(10) 0.7611(2) 0.2235(3) 0.0359(15) Uani 1 1 d . . . . .
C10 C 0.7106(9) 0.7084(2) 0.3289(3) 0.0330(14) Uani 1 1 d . . . . .
C7 C 1.0055(10) 0.6348(2) 0.2373(3) 0.0388(14) Uani 1 1 d . . . . .
C12 C 0.3605(10) 0.7934(2) 0.3432(3) 0.0378(14) Uani 1 1 d . . . . .
C8 C 1.0466(9) 0.6309(2) 0.3101(3) 0.0480(16) Uani 1 1 d . . . . .
H8 H 1.177294 0.602269 0.329867 0.058 Uiso 1 1 calc R U . . .
C11 C 0.5602(10) 0.7472(2) 0.3755(3) 0.0449(16) Uani 1 1 d . . . . .
C19 C 0.4162(10) 0.7673(3) 0.1507(3) 0.0529(17) Uani 1 1 d . . . . .
H19 H 0.286919 0.796386 0.131079 0.063 Uiso 1 1 calc R U . . .
C17 C 0.3073(10) 0.8006(2) 0.2696(3) 0.0341(14) Uani 1 1 d . . . . .
C13 C 0.2161(10) 0.8303(2) 0.3876(3) 0.0478(16) Uani 1 1 d . . . . .
H13 H 0.254926 0.826160 0.436670 0.057 Uiso 1 1 calc R U . . .
C24 C 0.9857(8) 0.6541(2) 0.4354(2) 0.0486(15) Uani 1 1 d . . . . .
H24A H 0.981009 0.697073 0.460307 0.058 Uiso 1 1 calc R U . . .
H24B H 1.161531 0.637519 0.442473 0.058 Uiso 1 1 calc R U . . .
C21 C 0.7466(10) 0.6876(3) 0.1324(3) 0.0451(16) Uani 1 1 d . . . . .
C6 C 1.1659(11) 0.5936(3) 0.1928(3) 0.0509(17) Uani 1 1 d . . . . .
C14 C 0.0188(11) 0.8725(3) 0.3613(3) 0.0590(18) Uani 1 1 d . . . . .
H14 H -0.078060 0.896176 0.391386 0.071 Uiso 1 1 calc R U . . .
C20 C 0.5576(11) 0.7315(3) 0.1059(3) 0.0565(17) Uani 1 1 d . . . . .
H20 H 0.523398 0.737362 0.056947 0.068 Uiso 1 1 calc R U . . .
C15 C -0.0300(10) 0.8784(2) 0.2877(3) 0.0589(18) Uani 1 1 d . . . . .
H15 H -0.161452 0.907076 0.268497 0.071 Uiso 1 1 calc R U . . .
C25 C 0.8110(9) 0.6034(2) 0.4680(3) 0.0484(15) Uani 1 1 d . . . . .
H25A H 0.632972 0.617393 0.456894 0.058 Uiso 1 1 calc R U . . .
H25B H 0.829635 0.559029 0.446863 0.058 Uiso 1 1 calc R U . . .
C1 C 1.1255(10) 0.5939(3) 0.1197(3) 0.0546(17) Uani 1 1 d . . . . .
C16 C 0.1082(10) 0.8435(3) 0.2425(3) 0.0534(16) Uani 1 1 d . . . . .
H16 H 0.069032 0.848447 0.193532 0.064 Uiso 1 1 calc R U . . .
C5 C 1.3632(11) 0.5521(3) 0.2247(3) 0.0625(18) Uani 1 1 d . . . . .
H5 H 1.397909 0.551495 0.274084 0.075 Uiso 1 1 calc R U . . .
C4 C 1.5081(13) 0.5118(3) 0.1845(4) 0.084(3) Uani 1 1 d . . . . .
H4 H 1.639141 0.484491 0.206535 0.101 Uiso 1 1 calc R U . . .
C26 C 0.8751(10) 0.5982(2) 0.5483(3) 0.0625(18) Uani 1 1 d . . . . .
H26A H 1.051704 0.582834 0.558977 0.075 Uiso 1 1 calc R U . . .
H26B H 0.863039 0.642962 0.568898 0.075 Uiso 1 1 calc R U . . .
C3 C 1.4560(15) 0.5126(3) 0.1119(5) 0.092(3) Uani 1 1 d . . . . .
H3 H 1.549874 0.484608 0.084818 0.111 Uiso 1 1 calc R U . . .
C27 C 0.7005(10) 0.5503(3) 0.5827(3) 0.088(2) Uani 1 1 d . . . . .
H27A H 0.529262 0.568642 0.578481 0.133 Uiso 1 1 calc R U . . .
H27B H 0.763399 0.544826 0.632091 0.133 Uiso 1 1 calc R U . . .
H27C H 0.697823 0.506990 0.559324 0.133 Uiso 1 1 calc R U . . .
C2 C 1.2703(14) 0.5533(3) 0.0786(4) 0.088(2) Uani 1 1 d . . . . .
H2 H 1.239825 0.554191 0.029165 0.105 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 C21 1.734(5) . ?
S1 C1 1.737(5) . ?
O1 C11 1.227(5) . ?
C9 C8 1.382(6) . ?
C9 C10 1.386(6) . ?
C9 C24 1.520(5) . ?
C22 C7 1.420(6) . ?
C22 C21 1.427(6) . ?
C22 C23 1.437(6) . ?
C23 C18 1.420(6) . ?
C23 C10 1.432(6) . ?
C18 C19 1.375(6) . ?
C18 C17 1.474(6) . ?
C10 C11 1.463(6) . ?
C7 C8 1.371(6) . ?
C7 C6 1.494(6) . ?
C12 C17 1.395(6) . ?
C12 C13 1.397(6) . ?
C12 C11 1.465(6) . ?
C8 H8 0.9300 . ?
C19 C20 1.381(6) . ?
C19 H19 0.9300 . ?
C17 C16 1.391(6) . ?
C13 C14 1.372(6) . ?
C13 H13 0.9300 . ?
C24 C25 1.531(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C21 C20 1.364(6) . ?
C6 C1 1.375(6) . ?
C6 C5 1.397(6) . ?
C14 C15 1.391(6) . ?
C14 H14 0.9300 . ?
C20 H20 0.9300 . ?
C15 C16 1.367(6) . ?
C15 H15 0.9300 . ?
C25 C26 1.520(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C1 C2 1.398(7) . ?
C16 H16 0.9300 . ?
C5 C4 1.385(7) . ?
C5 H5 0.9300 . ?
C4 C3 1.369(8) . ?
C4 H4 0.9300 . ?
C26 C27 1.512(6) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C3 C2 1.357(8) . ?
C3 H3 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C2 H2 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
C21 S1 C1 104.2(3) . . ?
C8 C9 C10 119.1(5) . . ?
C8 C9 C24 116.7(5) . . ?
C10 C9 C24 124.2(5) . . ?
C7 C22 C21 122.4(5) . . ?
C7 C22 C23 119.8(5) . . ?
C21 C22 C23 117.8(5) . . ?
C18 C23 C10 120.7(5) . . ?
C18 C23 C22 119.8(5) . . ?
C10 C23 C22 119.5(5) . . ?
C19 C18 C23 118.9(5) . . ?
C19 C18 C17 120.2(5) . . ?
C23 C18 C17 120.8(5) . . ?
C9 C10 C23 119.3(5) . . ?
C9 C10 C11 121.3(5) . . ?
C23 C10 C11 119.3(5) . . ?
C8 C7 C22 117.1(5) . . ?
C8 C7 C6 120.2(6) . . ?
C22 C7 C6 122.7(5) . . ?
C17 C12 C13 119.3(5) . . ?
C17 C12 C11 121.9(5) . . ?
C13 C12 C11 118.8(5) . . ?
C7 C8 C9 125.2(5) . . ?
C7 C8 H8 117.4 . . ?
C9 C8 H8 117.4 . . ?
O1 C11 C10 123.4(5) . . ?
O1 C11 C12 117.9(5) . . ?
C10 C11 C12 118.7(5) . . ?
C18 C19 C20 121.8(5) . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C16 C17 C12 118.8(5) . . ?
C16 C17 C18 122.6(5) . . ?
C12 C17 C18 118.5(5) . . ?
C14 C13 C12 122.2(5) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C9 C24 C25 113.3(4) . . ?
C9 C24 H24A 108.9 . . ?
C25 C24 H24A 108.9 . . ?
C9 C24 H24B 108.9 . . ?
C25 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C20 C21 C22 120.5(5) . . ?
C20 C21 S1 115.6(4) . . ?
C22 C21 S1 123.8(5) . . ?
C1 C6 C5 117.1(6) . . ?
C1 C6 C7 122.2(6) . . ?
C5 C6 C7 120.6(6) . . ?
C13 C14 C15 117.2(6) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C21 C20 C19 121.0(5) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C16 C15 C14 122.3(5) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C26 C25 C24 111.9(4) . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25B 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C6 C1 C2 121.8(6) . . ?
C6 C1 S1 124.5(5) . . ?
C2 C1 S1 113.6(6) . . ?
C15 C16 C17 120.2(5) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C4 C5 C6 121.5(6) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C3 C4 C5 119.1(7) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C27 C26 C25 113.5(4) . . ?
C27 C26 H26A 108.9 . . ?
C25 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C25 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C2 C3 C4 121.4(8) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C3 C2 C1 119.0(7) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C22 C23 C18 179.5(4) . . . . ?
C21 C22 C23 C18 -1.0(7) . . . . ?
C7 C22 C23 C10 -0.4(7) . . . . ?
C21 C22 C23 C10 179.0(4) . . . . ?
C10 C23 C18 C19 -179.7(5) . . . . ?
C22 C23 C18 C19 0.3(7) . . . . ?
C10 C23 C18 C17 0.5(7) . . . . ?
C22 C23 C18 C17 -179.5(4) . . . . ?
C8 C9 C10 C23 -2.1(7) . . . . ?
C24 C9 C10 C23 179.1(4) . . . . ?
C8 C9 C10 C11 -179.6(5) . . . . ?
C24 C9 C10 C11 1.6(7) . . . . ?
C18 C23 C10 C9 -178.1(4) . . . . ?
C22 C23 C10 C9 1.9(7) . . . . ?
C18 C23 C10 C11 -0.5(7) . . . . ?
C22 C23 C10 C11 179.4(4) . . . . ?
C21 C22 C7 C8 179.8(5) . . . . ?
C23 C22 C7 C8 -0.8(7) . . . . ?
C21 C22 C7 C6 -0.1(7) . . . . ?
C23 C22 C7 C6 179.3(5) . . . . ?
C22 C7 C8 C9 0.6(8) . . . . ?
C6 C7 C8 C9 -179.5(5) . . . . ?
C10 C9 C8 C7 0.8(8) . . . . ?
C24 C9 C8 C7 179.8(5) . . . . ?
C9 C10 C11 O1 -4.9(8) . . . . ?
C23 C10 C11 O1 177.6(5) . . . . ?
C9 C10 C11 C12 177.3(5) . . . . ?
C23 C10 C11 C12 -0.2(7) . . . . ?
C17 C12 C11 O1 -176.8(5) . . . . ?
C13 C12 C11 O1 1.9(8) . . . . ?
C17 C12 C11 C10 1.1(7) . . . . ?
C13 C12 C11 C10 179.8(5) . . . . ?
C23 C18 C19 C20 -0.2(8) . . . . ?
C17 C18 C19 C20 179.6(5) . . . . ?
C13 C12 C17 C16 -1.2(7) . . . . ?
C11 C12 C17 C16 177.5(5) . . . . ?
C13 C12 C17 C18 -179.8(5) . . . . ?
C11 C12 C17 C18 -1.1(7) . . . . ?
C19 C18 C17 C16 2.0(8) . . . . ?
C23 C18 C17 C16 -178.2(5) . . . . ?
C19 C18 C17 C12 -179.4(5) . . . . ?
C23 C18 C17 C12 0.4(7) . . . . ?
C17 C12 C13 C14 1.5(8) . . . . ?
C11 C12 C13 C14 -177.3(5) . . . . ?
C8 C9 C24 C25 -99.0(5) . . . . ?
C10 C9 C24 C25 79.9(6) . . . . ?
C7 C22 C21 C20 -178.9(5) . . . . ?
C23 C22 C21 C20 1.7(8) . . . . ?
C7 C22 C21 S1 0.2(7) . . . . ?
C23 C22 C21 S1 -179.2(4) . . . . ?
C1 S1 C21 C20 -179.3(4) . . . . ?
C1 S1 C21 C22 1.6(5) . . . . ?
C8 C7 C6 C1 177.5(5) . . . . ?
C22 C7 C6 C1 -2.5(8) . . . . ?
C8 C7 C6 C5 -1.6(8) . . . . ?
C22 C7 C6 C5 178.4(5) . . . . ?
C12 C13 C14 C15 -1.2(8) . . . . ?
C22 C21 C20 C19 -1.6(9) . . . . ?
S1 C21 C20 C19 179.2(4) . . . . ?
C18 C19 C20 C21 0.9(9) . . . . ?
C13 C14 C15 C16 0.7(9) . . . . ?
C9 C24 C25 C26 -174.0(4) . . . . ?
C5 C6 C1 C2 1.6(8) . . . . ?
C7 C6 C1 C2 -177.6(5) . . . . ?
C5 C6 C1 S1 -176.0(4) . . . . ?
C7 C6 C1 S1 4.9(7) . . . . ?
C21 S1 C1 C6 -4.2(5) . . . . ?
C21 S1 C1 C2 178.1(4) . . . . ?
C14 C15 C16 C17 -0.5(9) . . . . ?
C12 C17 C16 C15 0.7(8) . . . . ?
C18 C17 C16 C15 179.3(5) . . . . ?
C1 C6 C5 C4 -1.4(8) . . . . ?
C7 C6 C5 C4 177.7(5) . . . . ?
C6 C5 C4 C3 -0.2(10) . . . . ?
C24 C25 C26 C27 178.0(4) . . . . ?
C5 C4 C3 C2 1.8(11) . . . . ?
C4 C3 C2 C1 -1.6(11) . . . . ?
C6 C1 C2 C3 -0.1(10) . . . . ?
S1 C1 C2 C3 177.7(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C20 H20 O1 0.93 2.30 3.193(6) 160.5 4_575
C20 H20 O1 0.93 2.30 3.193(6) 160.5 4_575

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1955426'
loop_
_audit_author_name
_audit_author_address
'Bulat Gabidullin'
;University of Ottawa
Canada
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 O S'
_chemical_formula_weight         378.46

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.901(2)
_cell_length_b                   9.670(2)
_cell_length_c                   11.362(3)
_cell_angle_alpha                66.024(7)
_cell_angle_beta                 85.750(8)
_cell_angle_gamma                82.761(7)
_cell_volume                     886.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    621
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.39

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.197
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14119
_diffrn_reflns_av_unetI/netI     0.2600
_diffrn_reflns_av_R_equivalents  0.2036
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.962
_diffrn_reflns_theta_max         25.240
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3219
_reflns_number_gt                994
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX II (Bruker, 2009)'
_computing_cell_refinement       'APEX II (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0794P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3219
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2805
_refine_ls_R_factor_gt           0.0824
_refine_ls_wR_factor_ref         0.2332
_refine_ls_wR_factor_gt          0.1561
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.4365(3) 0.2721(3) 0.2795(2) 0.0497(7) Uani 1 1 d . . . . .
O1 O 0.5314(7) 0.3049(6) 0.9311(5) 0.071(2) Uani 1 1 d . . . . .
C23 C 0.4248(8) 0.3273(8) 0.6196(6) 0.0285(19) Uani 1 1 d . . . . .
C20 C 0.2722(8) 0.4365(7) 0.3865(7) 0.0338(19) Uani 1 1 d . . . . .
H20 H 0.2199 0.4755 0.3078 0.041 Uiso 1 1 calc R U . . .
C9 C 0.6283(8) 0.1544(7) 0.7609(6) 0.0296(19) Uani 1 1 d . . . . .
C6 C 0.6660(8) 0.1023(8) 0.4462(6) 0.0329(19) Uani 1 1 d . . . . .
C18 C 0.2956(8) 0.4338(8) 0.5985(7) 0.037(2) Uani 1 1 d . . . . .
C21 C 0.3945(8) 0.3304(8) 0.4033(6) 0.0335(19) Uani 1 1 d . . . . .
C22 C 0.4799(8) 0.2699(8) 0.5220(6) 0.0322(19) Uani 1 1 d . . . . .
C12 C 0.3186(8) 0.4401(8) 0.8134(7) 0.037(2) Uani 1 1 d . . . . .
C7 C 0.6058(9) 0.1617(8) 0.5431(6) 0.037(2) Uani 1 1 d . . . . .
C24 C 0.7185(8) 0.0796(8) 0.8846(6) 0.038(2) Uani 1 1 d . . . . .
H24 H 0.6464 0.0785 0.9567 0.045 Uiso 1 1 calc R U . . .
C10 C 0.5074(8) 0.2691(8) 0.7402(7) 0.0323(19) Uani 1 1 d . . . . .
C1 C 0.5999(8) 0.1444(7) 0.3269(7) 0.033(2) Uani 1 1 d . . . . .
C5 C 0.7967(8) -0.0019(8) 0.4680(6) 0.040(2) Uani 1 1 d . . . . .
H5 H 0.8482 -0.0319 0.5463 0.048 Uiso 1 1 calc R U . . .
C19 C 0.2207(9) 0.4904(8) 0.4832(7) 0.046(2) Uani 1 1 d . . . . .
H19 H 0.1356 0.5647 0.4688 0.055 Uiso 1 1 calc R U . . .
C4 C 0.8533(8) -0.0623(8) 0.3819(7) 0.041(2) Uani 1 1 d . . . . .
H4 H 0.9405 -0.1344 0.4018 0.050 Uiso 1 1 calc R U . . .
C8 C 0.6722(8) 0.1067(8) 0.6612(6) 0.039(2) Uani 1 1 d . . . . .
H8 H 0.7550 0.0298 0.6765 0.047 Uiso 1 1 calc R U . . .
C15 C 0.0592(9) 0.6376(8) 0.7801(8) 0.050(2) Uani 1 1 d . . . . .
H15 H -0.0307 0.7056 0.7684 0.060 Uiso 1 1 calc R U . . .
C11 C 0.4587(9) 0.3332(9) 0.8339(7) 0.046(2) Uani 1 1 d . . . . .
C2 C 0.6579(9) 0.0861(8) 0.2373(7) 0.041(2) Uani 1 1 d . . . . .
H2 H 0.6106 0.1186 0.1568 0.049 Uiso 1 1 calc R U . . .
C3 C 0.7827(9) -0.0177(8) 0.2653(7) 0.046(2) Uani 1 1 d . . . . .
H3 H 0.8214 -0.0594 0.2052 0.055 Uiso 1 1 calc R U . . .
C17 C 0.2378(9) 0.4879(8) 0.7009(7) 0.036(2) Uani 1 1 d . . . . .
C13 C 0.2680(9) 0.4957(8) 0.9080(7) 0.045(2) Uani 1 1 d . . . . .
H13 H 0.3242 0.4656 0.9839 0.054 Uiso 1 1 calc R U . . .
C25 C 0.8406(8) 0.1744(7) 0.8827(6) 0.044(2) Uani 1 1 d . . . . .
H25A H 0.9157 0.1765 0.8145 0.067 Uiso 1 1 calc R U . . .
H25B H 0.8900 0.1302 0.9662 0.067 Uiso 1 1 calc R U . . .
H25C H 0.7959 0.2783 0.8661 0.067 Uiso 1 1 calc R U . . .
C16 C 0.1062(9) 0.5870(8) 0.6858(7) 0.046(2) Uani 1 1 d . . . . .
H16 H 0.0490 0.6195 0.6101 0.055 Uiso 1 1 calc R U . . .
C14 C 0.1379(9) 0.5930(8) 0.8906(7) 0.049(2) Uani 1 1 d . . . . .
H14 H 0.1026 0.6293 0.9549 0.059 Uiso 1 1 calc R U . . .
C26 C 0.7803(9) -0.0836(8) 0.9156(7) 0.053(2) Uani 1 1 d . . . . .
H26A H 0.8670 -0.0866 0.8580 0.079 Uiso 1 1 calc R U . . .
H26B H 0.7012 -0.1385 0.9039 0.079 Uiso 1 1 calc R U . . .
H26C H 0.8128 -0.1318 1.0052 0.079 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 C21 1.718(7) . ?
S1 C1 1.748(7) . ?
O1 C11 1.236(8) . ?
C23 C18 1.408(9) . ?
C23 C22 1.460(9) . ?
C23 C10 1.467(9) . ?
C20 C21 1.366(9) . ?
C20 C19 1.421(9) . ?
C20 H20 0.9500 . ?
C9 C8 1.400(9) . ?
C9 C10 1.403(9) . ?
C9 C24 1.529(8) . ?
C6 C1 1.400(8) . ?
C6 C5 1.406(9) . ?
C6 C7 1.476(9) . ?
C18 C19 1.383(8) . ?
C18 C17 1.493(9) . ?
C21 C22 1.462(8) . ?
C22 C7 1.395(9) . ?
C12 C17 1.392(9) . ?
C12 C13 1.408(9) . ?
C12 C11 1.483(10) . ?
C7 C8 1.375(9) . ?
C24 C25 1.501(9) . ?
C24 C26 1.508(8) . ?
C24 H24 1.0000 . ?
C10 C11 1.451(10) . ?
C1 C2 1.391(9) . ?
C5 C4 1.366(8) . ?
C5 H5 0.9500 . ?
C19 H19 0.9500 . ?
C4 C3 1.388(9) . ?
C4 H4 0.9500 . ?
C8 H8 0.9500 . ?
C15 C14 1.367(9) . ?
C15 C16 1.368(9) . ?
C15 H15 0.9500 . ?
C2 C3 1.362(9) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C17 C16 1.390(9) . ?
C13 C14 1.369(9) . ?
C13 H13 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C16 H16 0.9500 . ?
C14 H14 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C21 S1 C1 104.8(4) . . ?
C18 C23 C22 120.7(7) . . ?
C18 C23 C10 121.5(7) . . ?
C22 C23 C10 117.8(6) . . ?
C21 C20 C19 122.0(7) . . ?
C21 C20 H20 119.0 . . ?
C19 C20 H20 119.0 . . ?
C8 C9 C10 118.3(6) . . ?
C8 C9 C24 117.4(6) . . ?
C10 C9 C24 124.3(7) . . ?
C1 C6 C5 114.9(6) . . ?
C1 C6 C7 123.6(7) . . ?
C5 C6 C7 121.5(6) . . ?
C19 C18 C23 120.9(7) . . ?
C19 C18 C17 119.0(7) . . ?
C23 C18 C17 120.1(7) . . ?
C20 C21 C22 120.7(7) . . ?
C20 C21 S1 115.9(5) . . ?
C22 C21 S1 123.4(6) . . ?
C7 C22 C23 121.2(6) . . ?
C7 C22 C21 122.6(7) . . ?
C23 C22 C21 116.2(7) . . ?
C17 C12 C13 119.6(7) . . ?
C17 C12 C11 120.8(8) . . ?
C13 C12 C11 119.6(7) . . ?
C8 C7 C22 117.5(7) . . ?
C8 C7 C6 119.7(7) . . ?
C22 C7 C6 122.8(7) . . ?
C25 C24 C26 111.7(6) . . ?
C25 C24 C9 110.8(6) . . ?
C26 C24 C9 114.1(6) . . ?
C25 C24 H24 106.6 . . ?
C26 C24 H24 106.6 . . ?
C9 C24 H24 106.6 . . ?
C9 C10 C11 122.8(7) . . ?
C9 C10 C23 119.4(7) . . ?
C11 C10 C23 117.8(7) . . ?
C2 C1 C6 122.7(7) . . ?
C2 C1 S1 114.6(5) . . ?
C6 C1 S1 122.7(6) . . ?
C4 C5 C6 123.1(7) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C18 C19 C20 119.5(7) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C5 C4 C3 119.7(7) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C7 C8 C9 125.6(7) . . ?
C7 C8 H8 117.2 . . ?
C9 C8 H8 117.2 . . ?
C14 C15 C16 121.8(8) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
O1 C11 C10 122.6(8) . . ?
O1 C11 C12 117.4(7) . . ?
C10 C11 C12 120.0(7) . . ?
C3 C2 C1 119.8(7) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.8(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C16 C17 C12 119.1(7) . . ?
C16 C17 C18 121.6(7) . . ?
C12 C17 C18 119.4(7) . . ?
C14 C13 C12 120.1(7) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C15 C16 C17 119.9(7) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C15 C14 C13 119.5(8) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 C23 C18 C19 -2.1(11) . . . . ?
C10 C23 C18 C19 178.5(7) . . . . ?
C22 C23 C18 C17 178.2(6) . . . . ?
C10 C23 C18 C17 -1.2(11) . . . . ?
C19 C20 C21 C22 -1.3(11) . . . . ?
C19 C20 C21 S1 177.4(6) . . . . ?
C1 S1 C21 C20 177.8(6) . . . . ?
C1 S1 C21 C22 -3.6(7) . . . . ?
C18 C23 C22 C7 -178.6(7) . . . . ?
C10 C23 C22 C7 0.8(10) . . . . ?
C18 C23 C22 C21 0.5(10) . . . . ?
C10 C23 C22 C21 179.9(6) . . . . ?
C20 C21 C22 C7 -179.8(7) . . . . ?
S1 C21 C22 C7 1.6(10) . . . . ?
C20 C21 C22 C23 1.2(10) . . . . ?
S1 C21 C22 C23 -177.4(5) . . . . ?
C23 C22 C7 C8 2.6(11) . . . . ?
C21 C22 C7 C8 -176.4(6) . . . . ?
C23 C22 C7 C6 -179.3(6) . . . . ?
C21 C22 C7 C6 1.7(11) . . . . ?
C1 C6 C7 C8 175.8(7) . . . . ?
C5 C6 C7 C8 -4.6(11) . . . . ?
C1 C6 C7 C22 -2.3(11) . . . . ?
C5 C6 C7 C22 177.3(7) . . . . ?
C8 C9 C24 C25 95.2(8) . . . . ?
C10 C9 C24 C25 -83.5(9) . . . . ?
C8 C9 C24 C26 -31.9(10) . . . . ?
C10 C9 C24 C26 149.5(7) . . . . ?
C8 C9 C10 C11 -176.2(7) . . . . ?
C24 C9 C10 C11 2.5(11) . . . . ?
C8 C9 C10 C23 4.2(10) . . . . ?
C24 C9 C10 C23 -177.2(6) . . . . ?
C18 C23 C10 C9 175.1(7) . . . . ?
C22 C23 C10 C9 -4.3(10) . . . . ?
C18 C23 C10 C11 -4.5(10) . . . . ?
C22 C23 C10 C11 176.1(7) . . . . ?
C5 C6 C1 C2 0.8(10) . . . . ?
C7 C6 C1 C2 -179.5(7) . . . . ?
C5 C6 C1 S1 179.8(5) . . . . ?
C7 C6 C1 S1 -0.6(10) . . . . ?
C21 S1 C1 C2 -177.9(5) . . . . ?
C21 S1 C1 C6 3.1(7) . . . . ?
C1 C6 C5 C4 -2.1(11) . . . . ?
C7 C6 C5 C4 178.3(7) . . . . ?
C23 C18 C19 C20 2.0(11) . . . . ?
C17 C18 C19 C20 -178.2(7) . . . . ?
C21 C20 C19 C18 -0.3(11) . . . . ?
C6 C5 C4 C3 1.6(12) . . . . ?
C22 C7 C8 C9 -2.8(12) . . . . ?
C6 C7 C8 C9 179.0(7) . . . . ?
C10 C9 C8 C7 -0.6(11) . . . . ?
C24 C9 C8 C7 -179.4(7) . . . . ?
C9 C10 C11 O1 9.0(12) . . . . ?
C23 C10 C11 O1 -171.3(7) . . . . ?
C9 C10 C11 C12 -172.4(7) . . . . ?
C23 C10 C11 C12 7.2(11) . . . . ?
C17 C12 C11 O1 174.4(7) . . . . ?
C13 C12 C11 O1 -4.6(12) . . . . ?
C17 C12 C11 C10 -4.3(11) . . . . ?
C13 C12 C11 C10 176.8(7) . . . . ?
C6 C1 C2 C3 0.8(11) . . . . ?
S1 C1 C2 C3 -178.2(6) . . . . ?
C1 C2 C3 C4 -1.3(12) . . . . ?
C5 C4 C3 C2 0.2(12) . . . . ?
C13 C12 C17 C16 -1.7(11) . . . . ?
C11 C12 C17 C16 179.4(7) . . . . ?
C13 C12 C17 C18 177.4(7) . . . . ?
C11 C12 C17 C18 -1.6(11) . . . . ?
C19 C18 C17 C16 3.6(11) . . . . ?
C23 C18 C17 C16 -176.6(7) . . . . ?
C19 C18 C17 C12 -175.4(7) . . . . ?
C23 C18 C17 C12 4.3(11) . . . . ?
C17 C12 C13 C14 1.8(11) . . . . ?
C11 C12 C13 C14 -179.3(7) . . . . ?
C14 C15 C16 C17 -0.3(12) . . . . ?
C12 C17 C16 C15 0.9(11) . . . . ?
C18 C17 C16 C15 -178.1(7) . . . . ?
C16 C15 C14 C13 0.4(12) . . . . ?
C12 C13 C14 C15 -1.1(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O1 0.95 2.55 3.442(8) 156.0 1_554
C2 H2 O1 0.95 2.55 3.442(8) 156.0 1_554

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
