# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_dasha4
_database_code_depnum_ccdc_archive 'CCDC 2062602'
loop_
_audit_author_name
_audit_author_address
'Olga Lodochnikova'
;Arbuzov Institute of Organic and Physical Chemistry
Russia
;
_audit_update_record             
;
2021-02-11 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;



# start Validation Reply
_vrf_RINTA01_dasha4              
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The studied crystal was grown from the melt 
as a thin plate. Crystal diffraction was very weak. 
;
_vrf_PLAT089_dasha4              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.33 Note  
RESPONSE: The studied crystal was grown from the melt 
as a thin plate. Crystal diffraction was very weak. 
;
_vrf_PLAT340_dasha4              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02556 Ang.  
RESPONSE: The studied crystal was grown from the melt 
as a thin plate. Crystal diffraction was very weak. 
;
# end Validation Reply

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H13 Cl2 N O2 S'
_chemical_formula_sum            'C17 H13 Cl2 N O2 S'
_exptl_crystal_recrystallization_method 'by slow cooling of the melt'
_chemical_melting_point          437.3

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         366.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'
_chemical_absolute_configuration ad

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'

_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.
;

_cell_length_a                   9.6734(7)
_cell_length_b                   9.6734(7)
_cell_length_c                   31.308(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2537.1(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1682
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      13.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    0.515
_shelx_estimated_absorpt_T_min   0.752
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7174
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Stalke et al., 2015)

 Equivalent reflections defined by point group 6 for scaling and error model
 Restraint esd for equal adjacent scale factors =  0.0050
 Maximum odd and even orders for spherical harmonics =   3   6
 wR2(int) =  0.0854 (selected reflections only, after parameter refinement)
 Estimated minimum and maximum transmission:  0.7174  0.9281
 Additional spherical absorption correction applied with mu*r =  0.0500
 Lambda/2 correction factor = 0.00150
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed x-ray tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41369
_diffrn_reflns_av_unetI/netI     0.1383
_diffrn_reflns_av_R_equivalents  0.2486
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         24.405
_diffrn_reflns_theta_full        24.405
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2784
_reflns_number_gt                1104
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.956
_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       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX3 v2019.11-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009);
Olex2 (Dolomanov et al., 2009); Mercury (Macrae, 2020)
;
_computing_publication_material  
;
WinGX (Farrugia, 2012); PLATON (Spek, 2009);
Olex2 (Dolomanov et al., 2009); enCIFer (Allen, 2004)
;
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 379 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     267
_refine_ls_number_restraints     304
_refine_ls_R_factor_all          0.2147
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.038
_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
Cl1 Cl 0.4175(5) 0.1585(5) 0.62184(11) 0.1054(13) Uani 1 1 d . . . . .
Cl2 Cl 0.7899(8) 0.2594(6) 0.34437(13) 0.158(2) Uani 1 1 d . . . . .
S1 S 0.5470(5) 0.3227(5) 0.52385(11) 0.1085(15) Uani 1 1 d . . . . .
O2 O 0.7030(10) 0.1189(11) 0.6552(3) 0.093(3) Uani 1 1 d . . . . .
O5 O 0.9172(13) 0.4392(12) 0.5442(3) 0.084(3) Uani 1 1 d D . . . .
H5 H 0.982(9) 0.444(11) 0.527(2) 0.05(4) Uiso 1 1 d D . . . .
C2 C 0.713(2) 0.1772(16) 0.6195(5) 0.084(4) Uani 1 1 d . . . . .
C3 C 0.5943(15) 0.2040(14) 0.5968(5) 0.069(3) Uani 1 1 d . . . . .
C4 C 0.6418(16) 0.2598(15) 0.5592(4) 0.072(4) Uani 1 1 d . . . . .
C5 C 0.8052(17) 0.2809(16) 0.5514(4) 0.072(4) Uani 1 1 d . . . . .
H50 H 0.802808 0.213661 0.527714 0.086 Uiso 1 1 calc R U . . .
N1 N 0.8349(13) 0.2254(11) 0.5921(3) 0.066(3) Uani 1 1 d D . . . .
C6 C 0.9787(14) 0.2238(14) 0.6014(3) 0.072(3) Uani 1 1 d D U . . .
H6AA H 0.990914 0.224387 0.632194 0.086 Uiso 0.59(2) 1 calc R U P A 1
H6AB H 1.068417 0.320907 0.590338 0.086 Uiso 0.59(2) 1 calc R U P A 1
H6BC H 0.993082 0.227319 0.632153 0.086 Uiso 0.41(2) 1 calc R U P A 2
H6BD H 1.068539 0.318654 0.589428 0.086 Uiso 0.41(2) 1 calc R U P A 2
C7A C 0.985(2) 0.0815(19) 0.5831(6) 0.068(4) Uani 0.59(2) 1 d D U P A 1
C8A C 0.872(3) -0.074(2) 0.5941(8) 0.096(6) Uani 0.59(2) 1 d D U P A 1
H8A H 0.787913 -0.090879 0.612106 0.115 Uiso 0.59(2) 1 calc R U P A 1
C9A C 0.881(3) -0.205(2) 0.5784(8) 0.098(6) Uani 0.59(2) 1 d D U P A 1
H9A H 0.804563 -0.309011 0.585130 0.118 Uiso 0.59(2) 1 calc R U P A 1
C10A C 1.006(4) -0.171(3) 0.5533(9) 0.097(6) Uani 0.59(2) 1 d D U P A 1
H10A H 1.019057 -0.255726 0.544228 0.117 Uiso 0.59(2) 1 calc R U P A 1
C11A C 1.115(3) -0.023(3) 0.5405(7) 0.083(5) Uani 0.59(2) 1 d D U P A 1
H11A H 1.195656 -0.008184 0.521701 0.100 Uiso 0.59(2) 1 calc R U P A 1
C12A C 1.105(3) 0.107(2) 0.5558(7) 0.071(5) Uani 0.59(2) 1 d D U P A 1
H12A H 1.180183 0.210164 0.547400 0.086 Uiso 0.59(2) 1 calc R U P A 1
C7B C 0.9779(14) 0.075(2) 0.5836(7) 0.075(5) Uani 0.41(2) 1 d D U P A 2
C8B C 0.935(4) -0.058(3) 0.6093(7) 0.086(6) Uani 0.41(2) 1 d D U P A 2
H8B H 0.907011 -0.057129 0.637647 0.104 Uiso 0.41(2) 1 calc R U P A 2
C9B C 0.934(4) -0.193(3) 0.5926(9) 0.093(7) Uani 0.41(2) 1 d D U P A 2
H9B H 0.907945 -0.281577 0.609733 0.112 Uiso 0.41(2) 1 calc R U P A 2
C10B C 0.972(4) -0.191(3) 0.5514(11) 0.092(7) Uani 0.41(2) 1 d D U P A 2
H10B H 0.964893 -0.283032 0.539938 0.110 Uiso 0.41(2) 1 calc R U P A 2
C11B C 1.019(4) -0.064(4) 0.5254(8) 0.086(6) Uani 0.41(2) 1 d D U P A 2
H11B H 1.046953 -0.066901 0.497142 0.103 Uiso 0.41(2) 1 calc R U P A 2
C12B C 1.024(4) 0.072(3) 0.5424(8) 0.078(6) Uani 0.41(2) 1 d D U P A 2
H12B H 1.058858 0.162295 0.525398 0.094 Uiso 0.41(2) 1 calc R U P A 2
C13 C 0.6194(17) 0.309(2) 0.4732(4) 0.074(4) Uani 1 1 d . . . . .
C14 C 0.5679(15) 0.164(2) 0.4564(5) 0.097(5) Uani 1 1 d . . . . .
H14 H 0.494862 0.074193 0.471384 0.117 Uiso 1 1 calc R U . . .
C15 C 0.621(2) 0.147(2) 0.4172(6) 0.115(5) Uani 1 1 d . . . . .
H15 H 0.588556 0.046500 0.406005 0.138 Uiso 1 1 calc R U . . .
C16 C 0.724(2) 0.282(3) 0.3948(4) 0.098(5) Uani 1 1 d . . . . .
C17 C 0.773(2) 0.426(2) 0.4112(6) 0.105(5) Uani 1 1 d . . . . .
H17 H 0.843592 0.517428 0.396165 0.127 Uiso 1 1 calc R U . . .
C18 C 0.717(2) 0.4379(19) 0.4510(5) 0.097(4) Uani 1 1 d . . . . .
H18 H 0.748114 0.538168 0.462327 0.117 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
Cl1 C3 1.726(12) . ?
Cl2 C16 1.759(15) . ?
S1 C4 1.731(12) . ?
S1 C13 1.767(12) . ?
O2 C2 1.232(15) . ?
O5 C5 1.382(14) . ?
O5 H5 0.817(15) . ?
C2 N1 1.338(15) . ?
C2 C3 1.483(18) . ?
C3 C4 1.281(14) . ?
C4 C5 1.509(16) . ?
C5 N1 1.465(14) . ?
C5 H50 0.9800 . ?
N1 C6 1.429(13) . ?
C6 C7A 1.521(17) . ?
C6 C7B 1.536(18) . ?
C6 H6AA 0.9700 . ?
C6 H6AB 0.9700 . ?
C6 H6BC 0.9700 . ?
C6 H6BD 0.9700 . ?
C7A C12A 1.365(18) . ?
C7A C8A 1.387(19) . ?
C8A C9A 1.405(19) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.34(2) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.34(2) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.39(2) . ?
C11A H11A 0.9300 . ?
C12A H12A 0.9300 . ?
C7B C12B 1.37(2) . ?
C7B C8B 1.40(2) . ?
C8B C9B 1.40(2) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.34(2) . ?
C9B H9B 0.9300 . ?
C10B C11B 1.35(2) . ?
C10B H10B 0.9300 . ?
C11B C12B 1.40(2) . ?
C11B H11B 0.9300 . ?
C12B H12B 0.9300 . ?
C13 C18 1.325(17) . ?
C13 C14 1.333(17) . ?
C14 C15 1.374(19) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.333(19) . ?
C17 C18 1.386(18) . ?
C17 H17 0.9300 . ?
C18 H18 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
C4 S1 C13 104.3(6) . . ?
C5 O5 H5 109(7) . . ?
O2 C2 N1 126.8(15) . . ?
O2 C2 C3 128.4(15) . . ?
N1 C2 C3 104.8(13) . . ?
C4 C3 C2 111.6(12) . . ?
C4 C3 Cl1 128.7(12) . . ?
C2 C3 Cl1 119.7(12) . . ?
C3 C4 C5 109.7(11) . . ?
C3 C4 S1 126.5(12) . . ?
C5 C4 S1 123.5(10) . . ?
O5 C5 N1 111.0(11) . . ?
O5 C5 C4 111.4(11) . . ?
N1 C5 C4 101.2(10) . . ?
O5 C5 H50 110.9 . . ?
N1 C5 H50 110.9 . . ?
C4 C5 H50 110.9 . . ?
C2 N1 C6 123.7(12) . . ?
C2 N1 C5 112.7(11) . . ?
C6 N1 C5 123.6(11) . . ?
N1 C6 C7A 114.3(12) . . ?
N1 C6 C7B 112.6(8) . . ?
N1 C6 H6AA 108.7 . . ?
C7A C6 H6AA 108.7 . . ?
N1 C6 H6AB 108.7 . . ?
C7A C6 H6AB 108.7 . . ?
H6AA C6 H6AB 107.6 . . ?
N1 C6 H6BC 109.1 . . ?
C7B C6 H6BC 109.1 . . ?
N1 C6 H6BD 109.1 . . ?
C7B C6 H6BD 109.1 . . ?
H6BC C6 H6BD 107.8 . . ?
C12A C7A C8A 119.6(16) . . ?
C12A C7A C6 119.3(15) . . ?
C8A C7A C6 121.1(15) . . ?
C7A C8A C9A 121.0(17) . . ?
C7A C8A H8A 119.5 . . ?
C9A C8A H8A 119.5 . . ?
C10A C9A C8A 116.5(19) . . ?
C10A C9A H9A 121.7 . . ?
C8A C9A H9A 121.7 . . ?
C9A C10A C11A 124.2(19) . . ?
C9A C10A H10A 117.9 . . ?
C11A C10A H10A 117.9 . . ?
C10A C11A C12A 119.4(17) . . ?
C10A C11A H11A 120.3 . . ?
C12A C11A H11A 120.3 . . ?
C7A C12A C11A 119.1(16) . . ?
C7A C12A H12A 120.4 . . ?
C11A C12A H12A 120.4 . . ?
C12B C7B C8B 118.1(17) . . ?
C12B C7B C6 120.9(17) . . ?
C8B C7B C6 121.0(17) . . ?
C7B C8B C9B 120.6(18) . . ?
C7B C8B H8B 119.7 . . ?
C9B C8B H8B 119.7 . . ?
C10B C9B C8B 118(2) . . ?
C10B C9B H9B 121.0 . . ?
C8B C9B H9B 121.0 . . ?
C9B C10B C11B 124(2) . . ?
C9B C10B H10B 117.9 . . ?
C11B C10B H10B 117.9 . . ?
C10B C11B C12B 118(2) . . ?
C10B C11B H11B 121.2 . . ?
C12B C11B H11B 121.2 . . ?
C7B C12B C11B 121.5(19) . . ?
C7B C12B H12B 119.3 . . ?
C11B C12B H12B 119.3 . . ?
C18 C13 C14 119.9(13) . . ?
C18 C13 S1 121.4(14) . . ?
C14 C13 S1 118.7(14) . . ?
C13 C14 C15 120.8(14) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 118.6(14) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C17 C16 C15 120.7(15) . . ?
C17 C16 Cl2 120.8(15) . . ?
C15 C16 Cl2 118.5(16) . . ?
C16 C17 C18 118.8(15) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C13 C18 C17 121.1(15) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 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
O2 C2 C3 C4 -176.6(12) . . . . ?
N1 C2 C3 C4 1.2(15) . . . . ?
O2 C2 C3 Cl1 2.8(18) . . . . ?
N1 C2 C3 Cl1 -179.3(8) . . . . ?
C2 C3 C4 C5 -0.8(15) . . . . ?
Cl1 C3 C4 C5 179.8(10) . . . . ?
C2 C3 C4 S1 -174.4(9) . . . . ?
Cl1 C3 C4 S1 6.2(18) . . . . ?
C13 S1 C4 C3 -157.3(13) . . . . ?
C13 S1 C4 C5 30.0(13) . . . . ?
C3 C4 C5 O5 -117.9(12) . . . . ?
S1 C4 C5 O5 55.9(15) . . . . ?
C3 C4 C5 N1 0.2(13) . . . . ?
S1 C4 C5 N1 174.0(9) . . . . ?
O2 C2 N1 C6 -4(2) . . . . ?
C3 C2 N1 C6 178.5(10) . . . . ?
O2 C2 N1 C5 176.8(12) . . . . ?
C3 C2 N1 C5 -1.1(14) . . . . ?
O5 C5 N1 C2 119.0(12) . . . . ?
C4 C5 N1 C2 0.6(13) . . . . ?
O5 C5 N1 C6 -60.6(15) . . . . ?
C4 C5 N1 C6 -178.9(11) . . . . ?
C2 N1 C6 C7A 99.5(14) . . . . ?
C5 N1 C6 C7A -81.0(16) . . . . ?
C2 N1 C6 C7B 97.6(15) . . . . ?
C5 N1 C6 C7B -82.8(16) . . . . ?
N1 C6 C7A C12A 121.5(19) . . . . ?
N1 C6 C7A C8A -59(2) . . . . ?
C12A C7A C8A C9A 2(3) . . . . ?
C6 C7A C8A C9A -177(2) . . . . ?
C7A C8A C9A C10A 1(4) . . . . ?
C8A C9A C10A C11A -4(5) . . . . ?
C9A C10A C11A C12A 4(5) . . . . ?
C8A C7A C12A C11A -2(3) . . . . ?
C6 C7A C12A C11A 177.1(18) . . . . ?
C10A C11A C12A C7A -1(4) . . . . ?
N1 C6 C7B C12B 85.4(18) . . . . ?
N1 C6 C7B C8B -96.5(17) . . . . ?
C12B C7B C8B C9B -2.2(19) . . . . ?
C6 C7B C8B C9B 179.7(13) . . . . ?
C7B C8B C9B C10B -1(3) . . . . ?
C8B C9B C10B C11B 4(4) . . . . ?
C9B C10B C11B C12B -2(4) . . . . ?
C8B C7B C12B C11B 4(3) . . . . ?
C6 C7B C12B C11B -178.0(17) . . . . ?
C10B C11B C12B C7B -2(4) . . . . ?
C4 S1 C13 C18 -110.3(12) . . . . ?
C4 S1 C13 C14 73.0(12) . . . . ?
C18 C13 C14 C15 4(2) . . . . ?
S1 C13 C14 C15 -179.7(12) . . . . ?
C13 C14 C15 C16 -3(2) . . . . ?
C14 C15 C16 C17 1(3) . . . . ?
C14 C15 C16 Cl2 -179.3(12) . . . . ?
C15 C16 C17 C18 -1(3) . . . . ?
Cl2 C16 C17 C18 179.7(11) . . . . ?
C14 C13 C18 C17 -3(2) . . . . ?
S1 C13 C18 C17 -179.8(11) . . . . ?
C16 C17 C18 C13 2(2) . . . . ?

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
_geom_hbond_publ_flag
O5 H5 O2 0.817(15) 1.90(3) 2.710(13) 170(10) 5_664 yes

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.054



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

data_dasha5
_database_code_depnum_ccdc_archive 'CCDC 2062603'
loop_
_audit_author_name
_audit_author_address
'Olga Lodochnikova'
;Arbuzov Institute of Organic and Physical Chemistry
Russia
;
_audit_update_record             
;
2021-02-11 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H13 Cl2 N O2 S'
_chemical_formula_sum            'C17 H13 Cl2 N O2 S'
_exptl_crystal_recrystallization_method 'from a benzene solution'
_chemical_melting_point          421.2

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         366.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_chemical_absolute_configuration ad

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

_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.
;

_cell_length_a                   9.0476(8)
_cell_length_b                   8.5404(8)
_cell_length_c                   11.4193(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.152(6)
_cell_angle_gamma                90
_cell_volume                     811.31(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1570
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      20.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.542
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.164
_exptl_absorpt_coefficient_mu    0.536
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6507
_exptl_absorpt_correction_T_max  0.7780
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Stalke et al., 2015)

 Equivalent reflections defined by point group 2 for scaling and error model
 Restraint esd for equal adjacent scale factors =  0.0050
 Maximum odd and even orders for spherical harmonics =   3   6
 wR2(int) =  0.0675 (selected reflections only, after parameter refinement)
 Estimated minimum and maximum transmission:  0.6507  0.7780
 Additional spherical absorption correction applied with mu*r =  0.1500
 Lambda/2 correction factor = 0.00150
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed x-ray tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12856
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         25.331
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2928
_reflns_number_gt                2139
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.990

_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       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'APEX3 v2019.11-0 (Bruker AXS)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
WinGX (Farrugia, 2012); ORTEP-3 (Farrugia, 2012); PLATON (Spek, 2009);
Olex2 (Dolomanov et al., 2009); Mercury (Macrae, 2020)
;
_computing_publication_material  
;
WinGX (Farrugia, 2012); PLATON (Spek, 2009);
Olex2 (Dolomanov et al., 2009); enCIFer (Allen, 2004)
;
_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_number_reflns         2928
_refine_ls_number_parameters     212
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_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
Cl1 Cl 0.29080(18) 0.45107(17) 0.62948(14) 0.0495(4) Uani 1 1 d . . . . .
Cl2 Cl 0.8862(2) 0.8178(2) 0.95492(17) 0.0681(6) Uani 1 1 d . . . . .
S1 S 0.3892(2) 0.6869(2) 0.40304(15) 0.0496(5) Uani 1 1 d . . . . .
O2 O -0.0805(5) 0.4387(5) 0.4890(4) 0.0476(11) Uani 1 1 d . . . . .
O5 O 0.0322(5) 0.8188(5) 0.2718(4) 0.0425(10) Uani 1 1 d D . . . .
H5 H 0.040(8) 0.875(6) 0.333(4) 0.06(2) Uiso 1 1 d D . . . .
N1 N -0.0642(5) 0.5842(5) 0.3255(4) 0.0356(11) Uani 1 1 d . . . . .
C2 C -0.0042(7) 0.5104(6) 0.4389(5) 0.0358(14) Uani 1 1 d . . . . .
C3 C 0.1715(6) 0.5339(6) 0.4886(5) 0.0319(13) Uani 1 1 d . . . . .
C4 C 0.2126(6) 0.6171(6) 0.4063(5) 0.0346(13) Uani 1 1 d . . . . .
C5 C 0.0582(6) 0.6599(6) 0.2922(5) 0.0339(13) Uani 1 1 d . . . . .
H50 H 0.060235 0.610984 0.215223 0.041 Uiso 1 1 calc R U . . .
C6 C -0.2320(6) 0.5780(7) 0.2370(5) 0.0413(15) Uani 1 1 d . . . . .
H6A H -0.262362 0.678542 0.194801 0.050 Uiso 1 1 calc R U . . .
H6B H -0.298773 0.559441 0.284508 0.050 Uiso 1 1 calc R U . . .
C7 C -0.2638(6) 0.4511(7) 0.1374(5) 0.0347(13) Uani 1 1 d . . . . .
C8 C -0.2284(7) 0.2950(7) 0.1721(6) 0.0440(16) Uani 1 1 d . . . . .
H8 H -0.186315 0.267327 0.257753 0.053 Uiso 1 1 calc R U . . .
C9 C -0.2553(7) 0.1809(8) 0.0804(6) 0.0545(17) Uani 1 1 d . . . . .
H9 H -0.230740 0.076882 0.104080 0.065 Uiso 1 1 calc R U . . .
C10 C -0.3180(8) 0.2216(9) -0.0452(7) 0.061(2) Uani 1 1 d . . . . .
H10 H -0.335203 0.144799 -0.106891 0.073 Uiso 1 1 calc R U . . .
C11 C -0.3560(9) 0.3737(10) -0.0814(7) 0.070(2) Uani 1 1 d . . . . .
H11 H -0.398640 0.400075 -0.167318 0.084 Uiso 1 1 calc R U . . .
C12 C -0.3306(7) 0.4890(8) 0.0106(6) 0.0500(18) Uani 1 1 d . . . . .
H12 H -0.359058 0.592182 -0.014112 0.060 Uiso 1 1 calc R U . . .
C13 C 0.5219(7) 0.7075(7) 0.5640(5) 0.0390(14) Uani 1 1 d . . . . .
C14 C 0.4780(7) 0.7896(7) 0.6491(6) 0.0432(16) Uani 1 1 d . . . . .
H14 H 0.372811 0.824739 0.624899 0.052 Uiso 1 1 calc R U . . .
C15 C 0.5895(7) 0.8197(8) 0.7700(6) 0.0448(15) Uani 1 1 d . . . . .
H15 H 0.559644 0.873136 0.828241 0.054 Uiso 1 1 calc R U . . .
C16 C 0.7452(7) 0.7702(7) 0.8039(6) 0.0439(16) Uani 1 1 d . . . . .
C17 C 0.7911(7) 0.6870(8) 0.7216(6) 0.0522(17) Uani 1 1 d . . . . .
H17 H 0.896688 0.652810 0.746404 0.063 Uiso 1 1 calc R U . . .
C18 C 0.6787(7) 0.6546(7) 0.6011(6) 0.0475(16) Uani 1 1 d . . . . .
H18 H 0.708126 0.597005 0.544602 0.057 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
Cl1 C3 1.699(5) . ?
Cl2 C16 1.742(6) . ?
S1 C4 1.720(6) . ?
S1 C13 1.765(6) . ?
O2 C2 1.220(6) . ?
O5 C5 1.381(7) . ?
O5 H5 0.824(14) . ?
N1 C2 1.347(7) . ?
N1 C5 1.456(7) . ?
N1 C6 1.457(6) . ?
C2 C3 1.477(8) . ?
C3 C4 1.342(8) . ?
C4 C5 1.533(7) . ?
C5 H50 0.9800 . ?
C6 C7 1.515(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C12 1.371(8) . ?
C7 C8 1.392(8) . ?
C8 C9 1.380(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.377(8) . ?
C13 C18 1.387(8) . ?
C14 C15 1.376(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(9) . ?
C17 C18 1.380(8) . ?
C17 H17 0.9300 . ?
C18 H18 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
C4 S1 C13 105.6(3) . . ?
C5 O5 H5 119(5) . . ?
C2 N1 C5 113.5(4) . . ?
C2 N1 C6 124.4(5) . . ?
C5 N1 C6 121.8(4) . . ?
O2 C2 N1 126.7(5) . . ?
O2 C2 C3 127.6(5) . . ?
N1 C2 C3 105.8(5) . . ?
C4 C3 C2 110.8(5) . . ?
C4 C3 Cl1 129.5(4) . . ?
C2 C3 Cl1 119.6(4) . . ?
C3 C4 C5 108.1(5) . . ?
C3 C4 S1 135.6(4) . . ?
C5 C4 S1 116.3(4) . . ?
O5 C5 N1 112.6(5) . . ?
O5 C5 C4 114.6(4) . . ?
N1 C5 C4 101.8(4) . . ?
O5 C5 H50 109.2 . . ?
N1 C5 H50 109.2 . . ?
C4 C5 H50 109.2 . . ?
N1 C6 C7 112.6(5) . . ?
N1 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C12 C7 C8 118.9(5) . . ?
C12 C7 C6 119.9(5) . . ?
C8 C7 C6 121.2(5) . . ?
C9 C8 C7 120.5(6) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 119.6(6) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.8(6) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 119.8(6) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.2(6) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C18 119.6(5) . . ?
C14 C13 S1 121.3(4) . . ?
C18 C13 S1 118.7(4) . . ?
C15 C14 C13 120.1(5) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 119.5(6) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 121.4(5) . . ?
C17 C16 Cl2 120.0(5) . . ?
C15 C16 Cl2 118.6(5) . . ?
C16 C17 C18 119.1(6) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C13 120.3(6) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 O2 179.7(6) . . . . ?
C6 N1 C2 O2 -6.1(9) . . . . ?
C5 N1 C2 C3 -0.5(6) . . . . ?
C6 N1 C2 C3 173.7(5) . . . . ?
O2 C2 C3 C4 179.1(6) . . . . ?
N1 C2 C3 C4 -0.7(6) . . . . ?
O2 C2 C3 Cl1 1.9(8) . . . . ?
N1 C2 C3 Cl1 -177.8(4) . . . . ?
C2 C3 C4 C5 1.5(6) . . . . ?
Cl1 C3 C4 C5 178.2(4) . . . . ?
C2 C3 C4 S1 179.3(5) . . . . ?
Cl1 C3 C4 S1 -3.9(9) . . . . ?
C13 S1 C4 C3 -25.9(7) . . . . ?
C13 S1 C4 C5 151.8(4) . . . . ?
C2 N1 C5 O5 -121.8(5) . . . . ?
C6 N1 C5 O5 63.8(6) . . . . ?
C2 N1 C5 C4 1.3(6) . . . . ?
C6 N1 C5 C4 -173.1(5) . . . . ?
C3 C4 C5 O5 120.1(5) . . . . ?
S1 C4 C5 O5 -58.2(6) . . . . ?
C3 C4 C5 N1 -1.7(6) . . . . ?
S1 C4 C5 N1 -180.0(4) . . . . ?
C2 N1 C6 C7 -94.2(6) . . . . ?
C5 N1 C6 C7 79.6(6) . . . . ?
N1 C6 C7 C12 -123.2(6) . . . . ?
N1 C6 C7 C8 57.7(7) . . . . ?
C12 C7 C8 C9 2.1(9) . . . . ?
C6 C7 C8 C9 -178.9(5) . . . . ?
C7 C8 C9 C10 -0.5(9) . . . . ?
C8 C9 C10 C11 -0.6(11) . . . . ?
C9 C10 C11 C12 0.0(12) . . . . ?
C8 C7 C12 C11 -2.7(10) . . . . ?
C6 C7 C12 C11 178.2(6) . . . . ?
C10 C11 C12 C7 1.7(11) . . . . ?
C4 S1 C13 C14 -52.0(6) . . . . ?
C4 S1 C13 C18 135.1(5) . . . . ?
C18 C13 C14 C15 0.4(9) . . . . ?
S1 C13 C14 C15 -172.4(5) . . . . ?
C13 C14 C15 C16 1.4(9) . . . . ?
C14 C15 C16 C17 -2.1(10) . . . . ?
C14 C15 C16 Cl2 177.0(5) . . . . ?
C15 C16 C17 C18 1.0(11) . . . . ?
Cl2 C16 C17 C18 -178.1(5) . . . . ?
C16 C17 C18 C13 0.8(10) . . . . ?
C14 C13 C18 C17 -1.5(9) . . . . ?
S1 C13 C18 C17 171.5(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
_geom_hbond_publ_flag
O5 H5 O2 0.824(14) 2.00(3) 2.787(6) 160(6) 2_556 yes

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.051



