# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_nc1081204
_database_code_depnum_ccdc_archive 'CCDC 2003255'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2019-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 F O4 S'
_chemical_formula_sum            'C19 H17 F O4 S'
_chemical_formula_weight         360.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H14 O4 F1 S1'
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'
F F 0.0171 0.0103 '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                   9.0958(2)
_cell_length_b                   11.0238(3)
_cell_length_c                   16.3016(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.035(2)
_cell_angle_gamma                90
_cell_volume                     1618.52(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8994
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9180
_cell_measurement_theta_min      2.2350
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16444
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.990
_diffrn_reflns_theta_min         2.237
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  31.00   0.50   23.00    --   10.60  42.00-177.00   56
  2  ω    -41.00 -16.00   0.50   23.00    --   10.60 -42.00  29.00   50
  3  ω     16.00  43.00   0.50   23.00    --  -10.90  42.00-177.00   54
  4  ω    -62.00 -37.00   0.50   23.00    --  -10.90 -42.00  29.00   50
  5  ω      2.00  28.00   0.50   23.00    --   10.60  77.00-180.00   52
  6  ω     30.00 100.00   0.50   23.00    --   10.60  57.00 -60.00  140
  7  ω    -17.00  69.00   0.50   23.00    --   10.60  82.00-120.00  172
  8  ω    -76.00 -47.00   0.50   23.00    --   10.60 -77.00 -90.00   58
  9  ω      7.00  32.00   0.50   23.00    --   10.60 -77.00 -90.00   50
 10  ω    -43.00  60.00   0.50   23.00    --  -10.90  38.00-150.00  206
 11  ω    -34.00  -9.00   0.50   23.00    --  -10.90  57.00-120.00   50
 12  ω    -36.00  77.00   0.50   23.00    --  -10.90  77.00  60.00  226
 13  ω     48.00  73.00   0.50   23.00    --  -10.90  57.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0602224000
_diffrn_orient_matrix_UB_12      -0.0094258000
_diffrn_orient_matrix_UB_13      0.0226036000
_diffrn_orient_matrix_UB_21      -0.0476066000
_diffrn_orient_matrix_UB_22      0.0323286000
_diffrn_orient_matrix_UB_23      -0.0305855000
_diffrn_orient_matrix_UB_31      -0.0176665000
_diffrn_orient_matrix_UB_32      -0.0548449000
_diffrn_orient_matrix_UB_33      -0.0219679000
_diffrn_oxdiff_digest_frames     
;
01ab3f5303e9dd7755bdd66db3ccbe9b15000251534
;
_diffrn_oxdiff_digest_hkl        
;
01a2edcfcd304c08a26753969439e8e16b027e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2923
_reflns_number_total             3383
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.037
_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)+(0.0288P)²+1.0171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.87634(4) 0.33792(3) 0.19927(2) 0.01586(10) Uani 1 1 d . . . . .
F1 F 0.47369(12) 0.86316(9) 0.00986(6) 0.0349(3) Uani 1 1 d . . . . .
O1 O 0.76927(11) 0.60132(10) 0.22125(7) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.39689(11) 0.40111(10) 0.12058(6) 0.0204(2) Uani 1 1 d . . . . .
O3 O 0.95563(11) 0.41455(10) 0.14884(7) 0.0214(3) Uani 1 1 d . . . . .
O4 O 0.85416(12) 0.21220(10) 0.17578(7) 0.0225(3) Uani 1 1 d . . . . .
C1 C 0.45575(19) 0.75004(15) 0.03962(10) 0.0239(4) Uani 1 1 d . . . . .
C2 C 0.56971(17) 0.69906(15) 0.09290(9) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.6589 0.7430 0.1090 0.024 Uiso 1 1 calc R . . . .
C3 C 0.55281(16) 0.58215(14) 0.12294(9) 0.0168(3) Uani 1 1 d . . . . .
C4 C 0.41957(16) 0.51943(15) 0.09735(9) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.30593(18) 0.57488(16) 0.04493(10) 0.0238(4) Uani 1 1 d . . . . .
H5 H 0.2155 0.5326 0.0288 0.029 Uiso 1 1 calc R . . . .
C6 C 0.32325(18) 0.69144(17) 0.01588(10) 0.0262(4) Uani 1 1 d . . . . .
H6 H 0.2453 0.7299 -0.0196 0.031 Uiso 1 1 calc R . . . .
C7 C 0.68001(15) 0.53352(14) 0.18275(9) 0.0162(3) Uani 1 1 d . . . . .
C8 C 0.68999(15) 0.39673(14) 0.19543(9) 0.0157(3) Uani 1 1 d . . . . .
H8 H 0.6288 0.3586 0.1464 0.019 Uiso 1 1 calc R . . . .
C9 C 0.61651(16) 0.36296(15) 0.27258(9) 0.0185(3) Uani 1 1 d . . . . .
H9A H 0.6024 0.2740 0.2744 0.022 Uiso 1 1 calc R . . . .
H9B H 0.6824 0.3874 0.3234 0.022 Uiso 1 1 calc R . . . .
C10 C 0.46758(16) 0.42581(14) 0.26978(9) 0.0177(3) Uani 1 1 d . . . . .
C11 C 0.34852(17) 0.38768(16) 0.20173(10) 0.0222(4) Uani 1 1 d . . . . .
H11A H 0.3220 0.3019 0.2101 0.027 Uiso 1 1 calc R . . . .
H11B H 0.2587 0.4377 0.2039 0.027 Uiso 1 1 calc R . . . .
C12 C 0.44391(18) 0.51212(16) 0.32256(11) 0.0241(4) Uani 1 1 d . . . . .
C13 C 0.96417(15) 0.34054(14) 0.30269(9) 0.0156(3) Uani 1 1 d . . . . .
C14 C 1.03066(16) 0.44663(15) 0.33502(10) 0.0189(3) Uani 1 1 d . . . . .
H14 H 1.0284 0.5178 0.3020 0.023 Uiso 1 1 calc R . . . .
C15 C 1.10059(16) 0.44717(15) 0.41638(10) 0.0209(3) Uani 1 1 d . . . . .
H15 H 1.1473 0.5193 0.4387 0.025 Uiso 1 1 calc R . . . .
C16 C 1.10352(16) 0.34387(15) 0.46595(9) 0.0205(3) Uani 1 1 d . . . . .
C17 C 1.03558(17) 0.23861(15) 0.43178(10) 0.0227(4) Uani 1 1 d . . . . .
H17 H 1.0370 0.1675 0.4648 0.027 Uiso 1 1 calc R . . . .
C18 C 0.96599(16) 0.23565(15) 0.35048(10) 0.0206(3) Uani 1 1 d . . . . .
H18 H 0.9203 0.1633 0.3278 0.025 Uiso 1 1 calc R . . . .
C19 C 1.17987(18) 0.34408(17) 0.55397(10) 0.0278(4) Uani 1 1 d . . . . .
H19A H 1.2078 0.4273 0.5707 0.042 Uiso 1 1 calc GR . . . .
H19B H 1.2692 0.2935 0.5582 0.042 Uiso 1 1 calc GR . . . .
H19C H 1.1124 0.3116 0.5904 0.042 Uiso 1 1 calc GR . . . .
H12A H 0.517(2) 0.5367(16) 0.3652(11) 0.026(5) Uiso 1 1 d . . . . .
H12B H 0.347(2) 0.5543(17) 0.3181(11) 0.031(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.4407(11) . ?
S1 O4 1.4445(12) . ?
S1 C8 1.8077(14) . ?
S1 C13 1.7620(15) . ?
F1 C1 1.3562(19) . ?
O1 C7 1.2121(18) . ?
O2 C4 1.3817(19) . ?
O2 C11 1.4588(18) . ?
C1 C2 1.376(2) . ?
C1 C6 1.374(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(2) . ?
C3 C4 1.407(2) . ?
C3 C7 1.504(2) . ?
C4 C5 1.388(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.523(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.550(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.517(2) . ?
C10 C11 1.498(2) . ?
C10 C12 1.321(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.935(18) . ?
C12 H12B 0.993(19) . ?
C13 C14 1.387(2) . ?
C13 C18 1.393(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.394(2) . ?
C16 C17 1.394(2) . ?
C16 C19 1.504(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
O3 S1 O4 118.28(7) . . ?
O3 S1 C8 108.16(7) . . ?
O3 S1 C13 109.89(7) . . ?
O4 S1 C8 103.85(7) . . ?
O4 S1 C13 107.29(7) . . ?
C13 S1 C8 108.95(7) . . ?
C4 O2 C11 114.82(12) . . ?
F1 C1 C2 118.93(15) . . ?
F1 C1 C6 118.43(15) . . ?
C6 C1 C2 122.64(16) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.26(15) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 118.86(14) . . ?
C2 C3 C7 116.39(13) . . ?
C4 C3 C7 124.74(14) . . ?
O2 C4 C3 122.55(13) . . ?
O2 C4 C5 117.24(14) . . ?
C5 C4 C3 120.18(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.55(15) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.47(15) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O1 C7 C3 120.99(14) . . ?
O1 C7 C8 121.16(13) . . ?
C3 C7 C8 117.82(13) . . ?
S1 C8 H8 107.0 . . ?
C7 C8 S1 113.43(10) . . ?
C7 C8 H8 107.0 . . ?
C7 C8 C9 108.89(12) . . ?
C9 C8 S1 113.22(10) . . ?
C9 C8 H8 107.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 C8 110.52(12) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C11 C10 C9 116.38(14) . . ?
C12 C10 C9 122.40(15) . . ?
C12 C10 C11 121.19(15) . . ?
O2 C11 C10 111.38(12) . . ?
O2 C11 H11A 109.4 . . ?
O2 C11 H11B 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C10 C12 H12A 121.9(11) . . ?
C10 C12 H12B 121.0(11) . . ?
H12A C12 H12B 117.1(15) . . ?
C14 C13 S1 119.53(12) . . ?
C14 C13 C18 121.14(14) . . ?
C18 C13 S1 119.33(12) . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 118.95(15) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.27(15) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C19 121.36(15) . . ?
C17 C16 C15 118.48(14) . . ?
C17 C16 C19 120.16(15) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.28(15) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 H18 120.6 . . ?
C17 C18 C13 118.88(15) . . ?
C17 C18 H18 120.6 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
S1 C8 C9 C10 174.02(11) . . . . ?
S1 C13 C14 C15 -179.45(11) . . . . ?
S1 C13 C18 C17 179.92(11) . . . . ?
F1 C1 C2 C3 -179.19(13) . . . . ?
F1 C1 C6 C5 178.71(14) . . . . ?
O1 C7 C8 S1 -44.56(17) . . . . ?
O1 C7 C8 C9 82.48(16) . . . . ?
O2 C4 C5 C6 -177.00(14) . . . . ?
O3 S1 C8 C7 -29.76(12) . . . . ?
O3 S1 C8 C9 -154.50(11) . . . . ?
O3 S1 C13 C14 34.79(14) . . . . ?
O3 S1 C13 C18 -144.99(12) . . . . ?
O4 S1 C8 C7 -156.24(10) . . . . ?
O4 S1 C8 C9 79.03(12) . . . . ?
O4 S1 C13 C14 164.60(11) . . . . ?
O4 S1 C13 C18 -15.17(14) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 C7 -178.33(14) . . . . ?
C2 C1 C6 C5 -2.0(2) . . . . ?
C2 C3 C4 O2 176.43(13) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
C2 C3 C7 O1 21.3(2) . . . . ?
C2 C3 C7 C8 -160.68(13) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C3 C7 C8 S1 137.42(11) . . . . ?
C3 C7 C8 C9 -95.54(15) . . . . ?
C4 O2 C11 C10 -66.63(17) . . . . ?
C4 C3 C7 O1 -157.32(14) . . . . ?
C4 C3 C7 C8 20.7(2) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C6 C1 C2 C3 1.5(2) . . . . ?
C7 C3 C4 O2 -5.0(2) . . . . ?
C7 C3 C4 C5 176.83(14) . . . . ?
C7 C8 C9 C10 46.86(16) . . . . ?
C8 S1 C13 C14 -83.55(13) . . . . ?
C8 S1 C13 C18 96.67(13) . . . . ?
C8 C9 C10 C11 66.09(17) . . . . ?
C8 C9 C10 C12 -111.98(17) . . . . ?
C9 C10 C11 O2 -55.74(18) . . . . ?
C11 O2 C4 C3 83.36(17) . . . . ?
C11 O2 C4 C5 -98.40(15) . . . . ?
C12 C10 C11 O2 122.35(16) . . . . ?
C13 S1 C8 C7 89.66(12) . . . . ?
C13 S1 C8 C9 -35.07(13) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C14 C13 C18 C17 0.1(2) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
C14 C15 C16 C19 179.69(14) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C13 -0.2(2) . . . . ?
C18 C13 C14 C15 0.3(2) . . . . ?
C19 C16 C17 C18 -179.22(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.619
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_256
_database_code_depnum_ccdc_archive 'CCDC 2003257'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2020-01-01
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C22 H25 F O3 S)'
_chemical_formula_sum            'C11 H12.50 F0.50 O1.50 S0.50'
_chemical_formula_weight         194.24
_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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5216(3)
_cell_length_b                   14.9812(4)
_cell_length_c                   15.0603(3)
_cell_angle_alpha                114.737(2)
_cell_angle_beta                 100.424(2)
_cell_angle_gamma                104.503(2)
_cell_volume                     1974.08(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16189
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8360
_cell_measurement_theta_min      2.1060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            33783
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.076
_diffrn_reflns_theta_min         2.114
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00 -43.00   0.50   21.57    --   10.60 -36.00  37.00   54
  2  ω     12.00  37.00   0.50   21.57    --   10.60  36.00-166.00   50
  3  ω    -98.00 -71.00   0.50   21.57    --  -10.90 -36.00  37.00   54
  4  ω    -47.00 -12.00   0.50   21.57    --  -10.90 -36.00  37.00   70
  5  ω    -78.00  41.00   0.50   21.57    --   10.60 -57.00 -30.00  238
  6  ω    -16.00  13.00   0.50   21.57    --   10.60  82.00  60.00   58
  7  ω     -2.00  25.00   0.50   21.57    --   10.60  82.00 -90.00   54
  8  ω     42.00  99.00   0.50   21.57    --   10.60  82.00-120.00  114
  9  ω     48.00  75.00   0.50   21.57    --   10.60  82.00  60.00   54
 10  ω    -11.00  98.00   0.50   21.57    --   10.60  82.00 150.00  218
 11  ω    -12.00  17.00   0.50   21.57    --   10.60  82.00-120.00   58
 12  ω     -4.00  30.00   0.50   21.57    --   10.60  82.00  90.00   68
 13  ω    -19.00  36.00   0.50   21.57    --   10.60  57.00 150.00  110
 14  ω     52.00  77.00   0.50   21.57    --   10.60  57.00 150.00   50
 15  ω    -10.00  74.00   0.50   21.57    --   10.60  82.00 -60.00  168
 16  ω    -26.00  77.00   0.50   21.57    --  -10.90  82.00-180.00  206
 17  ω    -33.00  -6.00   0.50   21.57    --  -10.90 -77.00   0.00   54
 18  ω    -42.00 -17.00   0.50   21.57    --  -10.90 -77.00 -60.00   50
 19  ω    -44.00 -16.00   0.50   21.57    --  -10.90 -77.00 -30.00   56
 20  ω    -68.00  17.00   0.50   21.57    --  -10.90 -82.00-120.00  170
 21  ω    -92.00 -61.00   0.50   21.57    --  -10.90 -77.00 -60.00   62
 22  ω    -10.00  15.00   0.50   21.57    --  -10.90  36.00-166.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0200704000
_diffrn_orient_matrix_UB_12      -0.0369738000
_diffrn_orient_matrix_UB_13      0.0111404000
_diffrn_orient_matrix_UB_21      0.0528405000
_diffrn_orient_matrix_UB_22      0.0052792000
_diffrn_orient_matrix_UB_23      -0.0228045000
_diffrn_orient_matrix_UB_31      0.0471829000
_diffrn_orient_matrix_UB_32      0.0417200000
_diffrn_orient_matrix_UB_33      0.0486036000
_diffrn_oxdiff_digest_frames     
;
011cfcb5ccf321f6041f735e120babbcce00025f46d
;
_diffrn_oxdiff_digest_hkl        
;
0113b03b133e910161275d71d0324faedf3f93
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6292
_reflns_number_total             8215
_reflns_odcompleteness_completeness 99.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         8215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.079
_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)+(0.0613P)²+0.1245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1150
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C29(H29), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9B,H9A), C11(H11B,H11A), C12(H12B,H12A), C31(H31B,H31A), C33(H33B,H33A),
 C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18),
 C24(H24), C25(H25), C26(H26), C27(H27), C36(H36), C37(H37), C39(H39), C40(H40)
2.d Idealised Me refined as rotating group:
 C20(H20C,H20B,H20A), C21(H21B,H21A,H21C), C22(H22A,H22C,H22B), C42(H42A,H42C,
 H42B), C43(H43B,H43A,H43C), C44(H44B,H44A,H44C)
;
_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 0.54857(4) 0.55114(3) 0.68471(3) 0.02058(12) Uani 1 1 d . . . . .
F1 F 0.10770(10) 0.58278(7) 0.61626(7) 0.0308(2) Uani 1 1 d . . . . .
O1 O 0.08594(12) 0.33827(9) 0.61493(9) 0.0305(3) Uani 1 1 d . . . . .
O2 O 0.55348(12) 0.63410(8) 0.65886(8) 0.0255(3) Uani 1 1 d . . . . .
O3 O 0.61696(12) 0.47986(9) 0.63944(8) 0.0257(3) Uani 1 1 d . . . . .
C1 C 0.11662(18) 0.26505(14) 0.53623(13) 0.0275(4) Uani 1 1 d . . . . .
C2 C 0.0467(2) 0.15957(14) 0.50413(14) 0.0346(5) Uani 1 1 d . . . . .
H2 H -0.021111 0.140709 0.531671 0.042 Uiso 1 1 calc R . . . .
C3 C 0.0780(2) 0.08264(15) 0.43122(15) 0.0397(5) Uani 1 1 d . . . . .
H3 H 0.031429 0.011925 0.410077 0.048 Uiso 1 1 calc R . . . .
C4 C 0.1776(2) 0.10982(14) 0.38950(14) 0.0359(5) Uani 1 1 d . . . . .
H4 H 0.197818 0.057810 0.339830 0.043 Uiso 1 1 calc R . . . .
C5 C 0.24737(19) 0.21554(13) 0.42236(13) 0.0284(4) Uani 1 1 d . . . . .
H5 H 0.314398 0.233658 0.393935 0.034 Uiso 1 1 calc R . . . .
C6 C 0.21984(17) 0.29521(13) 0.49667(12) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.30194(17) 0.40968(12) 0.53296(12) 0.0213(4) Uani 1 1 d . . . . .
H7 H 0.373550 0.413904 0.499772 0.026 Uiso 1 1 calc R . . . .
C8 C 0.37148(17) 0.47356(13) 0.65325(12) 0.0207(4) Uani 1 1 d . . . . .
H8 H 0.367438 0.424154 0.680390 0.025 Uiso 1 1 calc R . . . .
C9 C 0.28645(17) 0.54111(14) 0.69692(12) 0.0252(4) Uani 1 1 d . . . . .
H9B H 0.259813 0.530908 0.751365 0.030 Uiso 1 1 calc R . . . .
H9A H 0.338948 0.615448 0.724217 0.030 Uiso 1 1 calc R . . . .
C10 C 0.15896(18) 0.50134(13) 0.60410(13) 0.0259(4) Uani 1 1 d . . . . .
C11 C 0.04003(19) 0.41244(14) 0.59515(14) 0.0297(4) Uani 1 1 d . . . . .
H11B H -0.006348 0.442240 0.643900 0.036 Uiso 1 1 calc R . . . .
H11A H -0.026876 0.375787 0.526152 0.036 Uiso 1 1 calc R . . . .
C12 C 0.21201(17) 0.46979(13) 0.51252(12) 0.0235(4) Uani 1 1 d . . . . .
H12B H 0.266686 0.531335 0.510832 0.028 Uiso 1 1 calc R . . . .
H12A H 0.136048 0.424800 0.447840 0.028 Uiso 1 1 calc R . . . .
C13 C 0.61362(17) 0.60701(12) 0.81980(12) 0.0194(4) Uani 1 1 d . . . . .
C14 C 0.65845(18) 0.54819(13) 0.85988(12) 0.0243(4) Uani 1 1 d . . . . .
H14 H 0.656180 0.481547 0.815918 0.029 Uiso 1 1 calc R . . . .
C15 C 0.70649(18) 0.58918(13) 0.96545(13) 0.0260(4) Uani 1 1 d . . . . .
H15 H 0.737371 0.549777 0.992243 0.031 Uiso 1 1 calc R . . . .
C16 C 0.70981(17) 0.68885(12) 1.03325(12) 0.0201(4) Uani 1 1 d . . . . .
C17 C 0.66377(17) 0.74613(12) 0.99086(12) 0.0226(4) Uani 1 1 d . . . . .
H17 H 0.664897 0.812473 1.034562 0.027 Uiso 1 1 calc R . . . .
C18 C 0.61599(17) 0.70619(12) 0.88428(12) 0.0219(4) Uani 1 1 d . . . . .
H18 H 0.586162 0.745518 0.856895 0.026 Uiso 1 1 calc R . . . .
C19 C 0.76443(18) 0.72975(13) 1.14977(12) 0.0237(4) Uani 1 1 d . . . . .
C20 C 0.9196(2) 0.74814(17) 1.18123(14) 0.0423(5) Uani 1 1 d . . . . .
H20C H 0.932716 0.683211 1.143438 0.063 Uiso 1 1 calc GR . . . .
H20B H 0.954462 0.772443 1.253987 0.063 Uiso 1 1 calc GR . . . .
H20A H 0.968741 0.800286 1.165959 0.063 Uiso 1 1 calc GR . . . .
C21 C 0.7465(2) 0.83307(13) 1.21199(13) 0.0332(5) Uani 1 1 d . . . . .
H21B H 0.777579 0.854028 1.284176 0.050 Uiso 1 1 calc GR . . . .
H21A H 0.650348 0.823888 1.190819 0.050 Uiso 1 1 calc GR . . . .
H21C H 0.800358 0.886613 1.200319 0.050 Uiso 1 1 calc GR . . . .
C22 C 0.6861(2) 0.64861(14) 1.17572(14) 0.0389(5) Uani 1 1 d . . . . .
H22A H 0.716081 0.676353 1.249266 0.058 Uiso 1 1 calc GR . . . .
H22C H 0.704506 0.585027 1.143129 0.058 Uiso 1 1 calc GR . . . .
H22B H 0.588276 0.633340 1.151130 0.058 Uiso 1 1 calc GR . . . .
S2 S 0.40526(5) 0.91799(3) 0.80763(3) 0.02224(12) Uani 1 1 d . . . . .
F2 F -0.00473(11) 0.97277(9) 0.86775(8) 0.0425(3) Uani 1 1 d . . . . .
O4 O -0.02001(13) 0.70632(9) 0.80042(9) 0.0349(3) Uani 1 1 d . . . . .
O5 O 0.42551(12) 1.02867(8) 0.86203(8) 0.0266(3) Uani 1 1 d . . . . .
O6 O 0.51024(12) 0.88329(9) 0.84225(9) 0.0293(3) Uani 1 1 d . . . . .
C23 C 0.06960(19) 0.69361(14) 0.87022(13) 0.0293(4) Uani 1 1 d . . . . .
C24 C 0.0227(2) 0.60060(14) 0.87356(15) 0.0357(5) Uani 1 1 d . . . . .
H24 H -0.067017 0.552373 0.833394 0.043 Uiso 1 1 calc R . . . .
C25 C 0.1083(2) 0.57912(15) 0.93610(16) 0.0395(5) Uani 1 1 d . . . . .
H25 H 0.076271 0.516542 0.938271 0.047 Uiso 1 1 calc R . . . .
C26 C 0.2420(2) 0.65052(15) 0.99575(15) 0.0374(5) Uani 1 1 d . . . . .
H26 H 0.299854 0.636521 1.038512 0.045 Uiso 1 1 calc R . . . .
C27 C 0.2887(2) 0.74300(14) 0.99120(13) 0.0316(4) Uani 1 1 d . . . . .
H27 H 0.378755 0.790659 1.031246 0.038 Uiso 1 1 calc R . . . .
C28 C 0.20485(19) 0.76654(13) 0.92847(12) 0.0256(4) Uani 1 1 d . . . . .
C29 C 0.26053(18) 0.86695(12) 0.92342(12) 0.0232(4) Uani 1 1 d . . . . .
H29 H 0.358626 0.904583 0.965938 0.028 Uiso 1 1 calc R . . . .
C30 C 0.24502(17) 0.84357(13) 0.80945(12) 0.0226(4) Uani 1 1 d . . . . .
H30 H 0.223439 0.768103 0.765121 0.027 Uiso 1 1 calc R . . . .
C31 C 0.12345(18) 0.87365(14) 0.77408(13) 0.0282(4) Uani 1 1 d . . . . .
H31B H 0.156301 0.935676 0.766345 0.034 Uiso 1 1 calc R . . . .
H31A H 0.056741 0.816015 0.708811 0.034 Uiso 1 1 calc R . . . .
C32 C 0.0593(2) 0.89614(14) 0.86036(14) 0.0319(4) Uani 1 1 d . . . . .
C33 C -0.0558(2) 0.79861(15) 0.84019(15) 0.0381(5) Uani 1 1 d . . . . .
H33B H -0.074427 0.810063 0.904078 0.046 Uiso 1 1 calc R . . . .
H33A H -0.139800 0.787148 0.790978 0.046 Uiso 1 1 calc R . . . .
C34 C 0.18063(19) 0.94061(13) 0.95724(13) 0.0298(4) Uani 1 1 d . . . . .
H34A H 0.149217 0.938599 1.013324 0.036 Uiso 1 1 calc R . . . .
H34B H 0.237260 1.012760 0.979013 0.036 Uiso 1 1 calc R . . . .
C35 C 0.38044(18) 0.88009(13) 0.67580(12) 0.0215(4) Uani 1 1 d . . . . .
C36 C 0.39756(18) 0.78815(13) 0.61306(13) 0.0260(4) Uani 1 1 d . . . . .
H36 H 0.420267 0.746132 0.639621 0.031 Uiso 1 1 calc R . . . .
C37 C 0.38046(18) 0.75965(13) 0.51041(13) 0.0268(4) Uani 1 1 d . . . . .
H37 H 0.391251 0.697634 0.468204 0.032 Uiso 1 1 calc R . . . .
C38 C 0.34752(17) 0.82127(13) 0.46856(12) 0.0212(4) Uani 1 1 d . . . . .
C39 C 0.33022(18) 0.91296(13) 0.53320(13) 0.0241(4) Uani 1 1 d . . . . .
H39 H 0.307747 0.955213 0.506872 0.029 Uiso 1 1 calc R . . . .
C40 C 0.34590(18) 0.94248(13) 0.63621(13) 0.0254(4) Uani 1 1 d . . . . .
H40 H 0.333309 1.003668 0.678343 0.030 Uiso 1 1 calc R . . . .
C41 C 0.33273(17) 0.78717(13) 0.35458(12) 0.0231(4) Uani 1 1 d . . . . .
C42 C 0.46843(19) 0.77519(14) 0.33628(13) 0.0316(4) Uani 1 1 d . . . . .
H42A H 0.544247 0.841432 0.380099 0.047 Uiso 1 1 calc GR . . . .
H42C H 0.460276 0.754113 0.265265 0.047 Uiso 1 1 calc GR . . . .
H42B H 0.485279 0.722557 0.352088 0.047 Uiso 1 1 calc GR . . . .
C43 C 0.21291(18) 0.67996(13) 0.28743(12) 0.0276(4) Uani 1 1 d . . . . .
H43B H 0.127903 0.687312 0.297754 0.041 Uiso 1 1 calc GR . . . .
H43A H 0.231184 0.629680 0.306565 0.041 Uiso 1 1 calc GR . . . .
H43C H 0.204707 0.655839 0.215965 0.041 Uiso 1 1 calc GR . . . .
C44 C 0.30341(19) 0.86630(13) 0.32296(13) 0.0292(4) Uani 1 1 d . . . . .
H44B H 0.293849 0.840970 0.251160 0.044 Uiso 1 1 calc GR . . . .
H44A H 0.378882 0.933174 0.363822 0.044 Uiso 1 1 calc GR . . . .
H44C H 0.219070 0.874538 0.334024 0.044 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4420(11) . ?
S1 O3 1.4408(11) . ?
S1 C8 1.7838(17) . ?
S1 C13 1.7584(16) . ?
F1 C10 1.4111(18) . ?
O1 C1 1.3928(19) . ?
O1 C11 1.432(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.397(2) . ?
C2 C3 1.380(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.387(2) . ?
C5 C6 1.390(2) . ?
C6 C7 1.513(2) . ?
C7 C8 1.566(2) . ?
C7 C12 1.534(2) . ?
C8 C9 1.538(2) . ?
C9 C10 1.527(2) . ?
C10 C11 1.520(2) . ?
C10 C12 1.517(2) . ?
C13 C14 1.383(2) . ?
C13 C18 1.384(2) . ?
C14 C15 1.377(2) . ?
C15 C16 1.399(2) . ?
C16 C17 1.390(2) . ?
C16 C19 1.531(2) . ?
C17 C18 1.393(2) . ?
C19 C20 1.533(2) . ?
C19 C21 1.518(2) . ?
C19 C22 1.524(2) . ?
S2 O5 1.4453(11) . ?
S2 O6 1.4380(12) . ?
S2 C30 1.7852(17) . ?
S2 C35 1.7685(16) . ?
F2 C32 1.4460(19) . ?
O4 C23 1.389(2) . ?
O4 C33 1.436(2) . ?
C23 C24 1.382(2) . ?
C23 C28 1.398(2) . ?
C24 C25 1.376(3) . ?
C25 C26 1.384(3) . ?
C26 C27 1.384(2) . ?
C27 C28 1.389(2) . ?
C28 C29 1.511(2) . ?
C29 C30 1.569(2) . ?
C29 C34 1.528(2) . ?
C30 C31 1.538(2) . ?
C31 C32 1.524(2) . ?
C32 C33 1.517(3) . ?
C32 C34 1.513(2) . ?
C35 C36 1.385(2) . ?
C35 C40 1.385(2) . ?
C36 C37 1.383(2) . ?
C37 C38 1.392(2) . ?
C38 C39 1.392(2) . ?
C38 C41 1.537(2) . ?
C39 C40 1.388(2) . ?
C41 C42 1.541(2) . ?
C41 C43 1.535(2) . ?
C41 C44 1.526(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
O2 S1 C8 108.85(7) . . ?
O2 S1 C13 109.18(7) . . ?
O3 S1 O2 118.68(7) . . ?
O3 S1 C8 107.59(7) . . ?
O3 S1 C13 108.14(7) . . ?
C13 S1 C8 103.32(7) . . ?
C1 O1 C11 117.33(12) . . ?
O1 C1 C6 122.35(15) . . ?
C2 C1 O1 116.42(16) . . ?
C2 C1 C6 121.04(16) . . ?
C3 C2 C1 119.82(18) . . ?
C4 C3 C2 120.48(18) . . ?
C3 C4 C5 119.29(18) . . ?
C4 C5 C6 121.77(17) . . ?
C1 C6 C7 122.42(15) . . ?
C5 C6 C1 117.57(16) . . ?
C5 C6 C7 120.01(15) . . ?
C6 C7 C8 111.49(12) . . ?
C6 C7 C12 113.54(14) . . ?
C12 C7 C8 102.87(12) . . ?
C7 C8 S1 109.46(10) . . ?
C9 C8 S1 112.64(11) . . ?
C9 C8 C7 107.14(12) . . ?
C10 C9 C8 104.13(12) . . ?
F1 C10 C9 110.00(13) . . ?
F1 C10 C11 105.49(13) . . ?
F1 C10 C12 111.29(13) . . ?
C11 C10 C9 111.86(14) . . ?
C12 C10 C9 104.27(13) . . ?
C12 C10 C11 114.02(14) . . ?
O1 C11 C10 112.43(14) . . ?
C10 C12 C7 102.74(12) . . ?
C14 C13 S1 118.37(12) . . ?
C14 C13 C18 120.92(14) . . ?
C18 C13 S1 120.68(12) . . ?
C15 C14 C13 119.43(15) . . ?
C14 C15 C16 121.41(15) . . ?
C15 C16 C19 118.77(14) . . ?
C17 C16 C15 117.95(14) . . ?
C17 C16 C19 123.28(14) . . ?
C16 C17 C18 121.36(14) . . ?
C13 C18 C17 118.93(15) . . ?
C16 C19 C20 108.81(13) . . ?
C21 C19 C16 112.15(13) . . ?
C21 C19 C20 108.33(15) . . ?
C21 C19 C22 108.16(14) . . ?
C22 C19 C16 109.59(14) . . ?
C22 C19 C20 109.77(15) . . ?
O5 S2 C30 108.38(7) . . ?
O5 S2 C35 108.18(7) . . ?
O6 S2 O5 118.69(7) . . ?
O6 S2 C30 107.62(7) . . ?
O6 S2 C35 108.14(7) . . ?
C35 S2 C30 105.01(8) . . ?
C23 O4 C33 117.60(14) . . ?
O4 C23 C28 122.19(15) . . ?
C24 C23 O4 116.63(17) . . ?
C24 C23 C28 120.98(17) . . ?
C25 C24 C23 120.23(18) . . ?
C24 C25 C26 120.07(17) . . ?
C25 C26 C27 119.39(18) . . ?
C26 C27 C28 121.79(18) . . ?
C23 C28 C29 122.12(16) . . ?
C27 C28 C23 117.53(16) . . ?
C27 C28 C29 120.34(16) . . ?
C28 C29 C30 111.53(13) . . ?
C28 C29 C34 113.84(14) . . ?
C34 C29 C30 102.79(13) . . ?
C29 C30 S2 108.62(11) . . ?
C31 C30 S2 112.78(11) . . ?
C31 C30 C29 106.96(12) . . ?
C32 C31 C30 104.16(13) . . ?
F2 C32 C31 110.42(14) . . ?
F2 C32 C33 105.69(14) . . ?
F2 C32 C34 110.53(14) . . ?
C33 C32 C31 112.10(15) . . ?
C34 C32 C31 104.38(15) . . ?
C34 C32 C33 113.81(16) . . ?
O4 C33 C32 111.92(14) . . ?
C32 C34 C29 102.99(13) . . ?
C36 C35 S2 119.27(13) . . ?
C36 C35 C40 120.49(15) . . ?
C40 C35 S2 120.23(12) . . ?
C37 C36 C35 119.15(15) . . ?
C36 C37 C38 121.79(15) . . ?
C37 C38 C39 117.85(14) . . ?
C37 C38 C41 119.67(14) . . ?
C39 C38 C41 122.47(14) . . ?
C40 C39 C38 121.21(15) . . ?
C35 C40 C39 119.49(15) . . ?
C38 C41 C42 108.87(14) . . ?
C43 C41 C38 108.26(13) . . ?
C43 C41 C42 109.19(13) . . ?
C44 C41 C38 112.75(13) . . ?
C44 C41 C42 108.62(14) . . ?
C44 C41 C43 109.10(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.278
_oxdiff_exptl_absorpt_empirical_full_min 0.645
####################################################################### 
# 
# 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_nc1217nbf
_database_code_depnum_ccdc_archive 'CCDC 2003261'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2020-02-26
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 O3 S'
_chemical_formula_sum            'C16 H22 O3 S'
_chemical_formula_weight         294.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H22 O4 S1'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5686(2)
_cell_length_b                   9.5682(3)
_cell_length_c                   15.1726(5)
_cell_angle_alpha                105.346(3)
_cell_angle_beta                 92.676(2)
_cell_angle_gamma                102.631(3)
_cell_volume                     756.02(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9121
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9310
_cell_measurement_theta_min      2.2610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.071
_diffrn_reflns_theta_min         2.274
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00 100.00   0.50   20.02    --   10.60  82.00-180.00  234
  2  ω    -20.00 100.00   0.50   20.02    --   10.60  57.00 120.00  240
  3  ω    -15.00 100.00   0.50   20.02    --   10.60  77.00-120.00  230
  4  ω    -79.00  48.00   0.50   20.02    --   10.60 -38.00 -90.00  254
  5  ω    -20.00 100.00   0.50   20.02    --   10.60  57.00  30.00  240
  6  ω   -100.00  17.00   0.50   20.02    --  -10.90 -82.00-180.00  234
  7  ω   -100.00  15.00   0.50   20.02    --  -10.90 -77.00  30.00  230
  8  ω   -100.00  17.00   0.50   20.02    --  -10.90 -82.00 -30.00  234
  9  ω   -100.00  15.00   0.50   20.02    --  -10.90 -77.00-120.00  230
 10  ω    -38.00  70.00   0.50   20.02    --  -10.90  82.00-150.00  216
 11  ω    -41.00  79.00   0.50   20.02    --  -10.90  57.00 150.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0369165000
_diffrn_orient_matrix_UB_12      -0.0669743000
_diffrn_orient_matrix_UB_13      -0.0364629000
_diffrn_orient_matrix_UB_21      -0.0035962000
_diffrn_orient_matrix_UB_22      0.0422189000
_diffrn_orient_matrix_UB_23      -0.0318519000
_diffrn_orient_matrix_UB_31      0.1260010000
_diffrn_orient_matrix_UB_32      0.0013782000
_diffrn_orient_matrix_UB_33      -0.0059427000
_diffrn_oxdiff_digest_frames     
;
01e73e7a99737e7d7d71da12b6d046517600025949e
;
_diffrn_oxdiff_digest_hkl        
;
0112c011c53c9855edf9b8ecf9c248db84e7cf
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2685
_reflns_number_total             3170
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.088
_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)+(0.0639P)²+0.8050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1489
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.52321(11) 0.24997(7) 0.60828(4) 0.0276(2) Uani 1 1 d . . . . .
O1 O 0.1778(3) 0.41358(19) 0.89146(12) 0.0291(4) Uani 1 1 d . . . . .
O2 O 0.5854(4) 0.1277(2) 0.63606(13) 0.0402(5) Uani 1 1 d . . . . .
O3 O 0.7184(3) 0.3522(2) 0.58289(12) 0.0402(5) Uani 1 1 d . . . . .
C1 C 0.2866(4) 0.5519(3) 0.88386(15) 0.0243(5) Uani 1 1 d . . . . .
C2 C 0.4906(4) 0.5768(3) 0.83435(15) 0.0236(5) Uani 1 1 d . . . . .
C3 C 0.5951(5) 0.7218(3) 0.83332(15) 0.0267(5) Uani 1 1 d . . . . .
H3 H 0.731304 0.740278 0.801227 0.032 Uiso 1 1 calc R . . . .
C4 C 0.5001(5) 0.8393(3) 0.87924(16) 0.0296(6) Uani 1 1 d . . . . .
H4 H 0.573161 0.936206 0.878646 0.035 Uiso 1 1 calc R . . . .
C5 C 0.2952(5) 0.8119(3) 0.92622(16) 0.0294(6) Uani 1 1 d . . . . .
H5 H 0.228657 0.890556 0.955980 0.035 Uiso 1 1 calc R . . . .
C6 C 0.1894(5) 0.6692(3) 0.92914(16) 0.0281(5) Uani 1 1 d . . . . .
H6 H 0.053257 0.651697 0.961393 0.034 Uiso 1 1 calc R . . . .
C7 C 0.2688(5) 0.2880(3) 0.83897(17) 0.0262(5) Uani 1 1 d . . . . .
C8 C 0.1843(5) 0.2561(3) 0.73679(17) 0.0284(5) Uani 1 1 d . . . . .
H8A H 0.025886 0.280264 0.728651 0.034 Uiso 1 1 calc R . . . .
H8B H 0.167440 0.151521 0.705085 0.034 Uiso 1 1 calc R . . . .
C9 C 0.3856(4) 0.3553(3) 0.69911(15) 0.0226(5) Uani 1 1 d . . . . .
H9 H 0.313632 0.426013 0.676774 0.027 Uiso 1 1 calc R . . . .
C10 C 0.5796(4) 0.4426(3) 0.78411(15) 0.0247(5) Uani 1 1 d . . . . .
H10 H 0.748490 0.468643 0.767691 0.030 Uiso 1 1 calc R . . . .
C11 C 0.5496(5) 0.3344(3) 0.84394(17) 0.0283(5) Uani 1 1 d . . . . .
C12 C 0.1678(5) 0.1621(3) 0.8795(2) 0.0371(6) Uani 1 1 d . . . . .
H12A H 0.231999 0.189543 0.943110 0.056 Uiso 1 1 calc GR . . . .
H12B H 0.216694 0.074057 0.846758 0.056 Uiso 1 1 calc GR . . . .
H12C H -0.009652 0.142486 0.874335 0.056 Uiso 1 1 calc GR . . . .
C13 C 0.2836(5) 0.1721(3) 0.51597(16) 0.0282(5) Uani 1 1 d . . . . .
H13A H 0.338171 0.099315 0.468665 0.034 Uiso 1 1 calc R . . . .
H13B H 0.140704 0.119042 0.538004 0.034 Uiso 1 1 calc R . . . .
C14 C 0.2024(4) 0.2823(3) 0.47234(16) 0.0251(5) Uani 1 1 d . . . . .
H14A H 0.344049 0.338702 0.451524 0.030 Uiso 1 1 calc R . . . .
H14B H 0.136271 0.351958 0.517652 0.030 Uiso 1 1 calc R . . . .
C15 C 0.0053(5) 0.2003(3) 0.39110(17) 0.0331(6) Uani 1 1 d . . . . .
H15A H 0.079304 0.141044 0.342705 0.040 Uiso 1 1 calc R . . . .
H15B H -0.123966 0.132554 0.410428 0.040 Uiso 1 1 calc R . . . .
C16 C -0.1096(6) 0.3046(3) 0.35293(19) 0.0404(7) Uani 1 1 d . . . . .
H16A H -0.225790 0.247657 0.300238 0.061 Uiso 1 1 calc GR . . . .
H16B H 0.017848 0.373866 0.335203 0.061 Uiso 1 1 calc GR . . . .
H16C H -0.193764 0.358461 0.399132 0.061 Uiso 1 1 calc GR . . . .
H11A H 0.609(5) 0.246(3) 0.8175(18) 0.026(7) Uiso 1 1 d . . . . .
H11B H 0.632(5) 0.383(3) 0.901(2) 0.032(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4458(19) . ?
S1 O3 1.435(2) . ?
S1 C9 1.790(2) . ?
S1 C13 1.771(2) . ?
O1 C1 1.367(3) . ?
O1 C7 1.460(3) . ?
C1 C2 1.402(3) . ?
C1 C6 1.385(3) . ?
C2 C3 1.387(3) . ?
C2 C10 1.507(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.387(4) . ?
C5 C6 1.377(4) . ?
C7 C8 1.529(3) . ?
C7 C11 1.522(3) . ?
C7 C12 1.507(4) . ?
C8 C9 1.538(3) . ?
C9 C10 1.560(3) . ?
C10 C11 1.536(4) . ?
C13 C14 1.518(3) . ?
C14 C15 1.524(3) . ?
C15 C16 1.514(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
O2 S1 C9 108.67(11) . . ?
O2 S1 C13 107.44(12) . . ?
O3 S1 O2 117.86(13) . . ?
O3 S1 C9 107.95(11) . . ?
O3 S1 C13 109.38(12) . . ?
C13 S1 C9 104.77(11) . . ?
C1 O1 C7 117.19(18) . . ?
O1 C1 C2 122.4(2) . . ?
O1 C1 C6 116.9(2) . . ?
C6 C1 C2 120.6(2) . . ?
C1 C2 C10 117.4(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 C10 124.1(2) . . ?
C4 C3 C2 121.0(2) . . ?
C3 C4 C5 119.6(2) . . ?
C6 C5 C4 120.5(2) . . ?
C5 C6 C1 119.7(2) . . ?
O1 C7 C8 109.22(19) . . ?
O1 C7 C11 109.3(2) . . ?
O1 C7 C12 104.88(19) . . ?
C11 C7 C8 103.3(2) . . ?
C12 C7 C8 114.4(2) . . ?
C12 C7 C11 115.6(2) . . ?
C7 C8 C9 106.13(19) . . ?
C8 C9 S1 112.75(16) . . ?
C8 C9 C10 104.53(18) . . ?
C10 C9 S1 111.44(15) . . ?
C2 C10 C9 107.10(18) . . ?
C2 C10 C11 107.40(19) . . ?
C11 C10 C9 102.46(19) . . ?
C7 C11 C10 100.72(19) . . ?
C14 C13 S1 115.77(17) . . ?
C13 C14 C15 110.43(19) . . ?
C16 C15 C14 113.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.617
_oxdiff_exptl_absorpt_empirical_full_min 0.593
####################################################################### 
# 
# 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_ncmsn19
_database_code_depnum_ccdc_archive 'CCDC 2003260'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2019-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 O4 S'
_chemical_formula_sum            'C13 H16 O4 S'
_chemical_formula_weight         268.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H16 O4 S1'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1912(3)
_cell_length_b                   6.0583(2)
_cell_length_c                   25.2332(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.806(4)
_cell_angle_gamma                90
_cell_volume                     1250.69(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5612
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.7240
_cell_measurement_theta_min      2.5760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10768
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.034
_diffrn_reflns_theta_min         2.580
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  -4.00   0.50    5.69    --   10.60 -73.00-114.00   52
  2  ω     31.00  57.00   0.50    5.69    --   10.60  73.00  14.00   52
  3  ω    -12.00  14.00   0.50    5.69    --  -10.90  73.00  14.00   52
  4  ω    -68.00 -43.00   0.50    5.69    --  -10.90 -73.00-114.00   50
  5  ω    -14.00  12.00   0.50    5.69    --   10.60  77.00 -30.00   52
  6  ω    -15.00 100.00   0.50    5.69    --   10.60  77.00 -60.00  230
  7  ω    -55.00  37.00   0.50    5.69    --   10.60 -57.00-180.00  184
  8  ω     -6.00  90.00   0.50    5.69    --   10.60  77.00  30.00  192
  9  ω   -100.00 -38.00   0.50    5.69    --  -10.90 -82.00 150.00  124
 10  ω    -32.00  -2.00   0.50    5.69    --  -10.90 -82.00 150.00   60
 11  ω     -7.00  18.00   0.50    5.69    --  -10.90  77.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0503405000
_diffrn_orient_matrix_UB_12      0.0608727000
_diffrn_orient_matrix_UB_13      0.0167882000
_diffrn_orient_matrix_UB_21      -0.0659755000
_diffrn_orient_matrix_UB_22      -0.0726745000
_diffrn_orient_matrix_UB_23      -0.0063936000
_diffrn_orient_matrix_UB_31      0.0250842000
_diffrn_orient_matrix_UB_32      -0.0686492000
_diffrn_orient_matrix_UB_33      0.0216754000
_diffrn_oxdiff_digest_frames     
;
01f71fb24bc7f4c6e6d79c471d793301580002509e5
;
_diffrn_oxdiff_digest_hkl        
;
015c616415bcaa2cc1ccaa31f44234f15fbf3b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2230
_reflns_number_total             2550
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.228
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0854
_refine_ls_restrained_S_all      1.195
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+12.5635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2050
_refine_ls_wR_factor_ref         0.2070
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.22592(15) 0.0852(2) 0.55569(5) 0.0131(3) Uani 1 1 d . . . . .
O1 O 0.4686(4) 0.7459(6) 0.64249(13) 0.0145(7) Uani 1 1 d . . . . .
C1 C 0.4734(6) 0.6203(8) 0.68883(19) 0.0135(10) Uani 1 1 d . . . . .
O2 O 0.1614(4) 0.5180(6) 0.62342(14) 0.0150(7) Uani 1 1 d . . . . .
H6 H 0.2123 0.6375 0.6206 0.022 Uiso 1 1 calc GR . . . .
C2 C 0.5645(6) 0.6931(9) 0.7332(2) 0.0176(11) Uani 1 1 d . . . . .
H1 H 0.6238 0.8276 0.7318 0.021 Uiso 1 1 calc R . . . .
O3 O 0.1105(5) -0.0265(6) 0.58801(14) 0.0210(8) Uani 1 1 d . . . . .
C3 C 0.5688(6) 0.5691(10) 0.7795(2) 0.0208(11) Uani 1 1 d . . . . .
H2 H 0.6314 0.6184 0.8099 0.025 Uiso 1 1 calc R . . . .
O4 O 0.3221(5) -0.0521(6) 0.52203(15) 0.0231(9) Uani 1 1 d . . . . .
C4 C 0.4815(7) 0.3724(10) 0.7813(2) 0.0209(12) Uani 1 1 d . . . . .
H3 H 0.4853 0.2861 0.8128 0.025 Uiso 1 1 calc R . . . .
C5 C 0.3888(6) 0.3035(9) 0.73694(19) 0.0166(10) Uani 1 1 d . . . . .
H4 H 0.3285 0.1698 0.7385 0.020 Uiso 1 1 calc R . . . .
C6 C 0.3821(6) 0.4270(8) 0.68983(18) 0.0116(9) Uani 1 1 d . . . . .
C7 C 0.2708(6) 0.3518(8) 0.64340(18) 0.0128(10) Uani 1 1 d . . . . .
H5 H 0.2003 0.2334 0.6578 0.015 Uiso 1 1 calc R . . . .
C8 C 0.3643(6) 0.2419(8) 0.59870(18) 0.0113(9) Uani 1 1 d . . . . .
H7 H 0.4411 0.1331 0.6163 0.014 Uiso 1 1 calc R . . . .
C9 C 0.4688(6) 0.3914(8) 0.56399(19) 0.0129(10) Uani 1 1 d . . . . .
H11 H 0.4997 0.3069 0.5324 0.015 Uiso 1 1 calc R . . . .
H12 H 0.4016 0.5185 0.5514 0.015 Uiso 1 1 calc R . . . .
C10 C 0.6237(6) 0.4780(8) 0.59285(18) 0.0132(10) Uani 1 1 d . . . . .
C11 C 0.6120(6) 0.7137(8) 0.6122(2) 0.0159(10) Uani 1 1 d . . . . .
H15 H 0.7109 0.7502 0.6346 0.019 Uiso 1 1 calc R . . . .
H16 H 0.6075 0.8150 0.5814 0.019 Uiso 1 1 calc R . . . .
C12 C 0.1187(6) 0.2776(9) 0.5153(2) 0.0192(11) Uani 1 1 d . . . . .
H8 H 0.0436 0.1995 0.4903 0.029 Uiso 1 1 calc GR . . . .
H9 H 0.1963 0.3643 0.4955 0.029 Uiso 1 1 calc GR . . . .
H10 H 0.0563 0.3763 0.5375 0.029 Uiso 1 1 calc GR . . . .
C13 C 0.7587(7) 0.3643(9) 0.5984(2) 0.0191(11) Uani 1 1 d . . . . .
H13 H 0.769(8) 0.230(13) 0.581(3) 0.037(19) Uiso 1 1 d . . . . .
H14 H 0.852(7) 0.435(10) 0.615(2) 0.015(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.446(4) . ?
S1 O4 1.449(4) . ?
S1 C8 1.801(5) . ?
S1 C12 1.756(5) . ?
O1 C1 1.394(6) . ?
O1 C11 1.446(6) . ?
C1 C2 1.386(7) . ?
C1 C6 1.390(7) . ?
O2 C7 1.424(6) . ?
C2 C3 1.388(8) . ?
C3 C4 1.392(8) . ?
C4 C5 1.386(7) . ?
C5 C6 1.404(7) . ?
C6 C7 1.519(6) . ?
C7 C8 1.545(6) . ?
C8 C9 1.547(6) . ?
C9 C10 1.525(7) . ?
C10 C11 1.514(7) . ?
C10 C13 1.304(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O4 116.8(2) . . ?
O3 S1 C8 108.4(2) . . ?
O3 S1 C12 108.4(2) . . ?
O4 S1 C8 108.2(2) . . ?
O4 S1 C12 108.1(2) . . ?
C12 S1 C8 106.4(2) . . ?
C1 O1 C11 112.3(4) . . ?
C2 C1 O1 119.7(4) . . ?
C2 C1 C6 121.5(5) . . ?
C6 C1 O1 118.8(4) . . ?
C1 C2 C3 119.9(5) . . ?
C2 C3 C4 120.0(5) . . ?
C5 C4 C3 119.6(5) . . ?
C4 C5 C6 121.3(5) . . ?
C1 C6 C5 117.8(4) . . ?
C1 C6 C7 122.8(4) . . ?
C5 C6 C7 119.4(4) . . ?
O2 C7 C6 113.9(4) . . ?
O2 C7 C8 111.8(4) . . ?
C6 C7 C8 113.1(4) . . ?
C7 C8 S1 110.4(3) . . ?
C7 C8 C9 117.9(4) . . ?
C9 C8 S1 108.5(3) . . ?
C10 C9 C8 113.7(4) . . ?
C11 C10 C9 114.5(4) . . ?
C13 C10 C9 123.4(5) . . ?
C13 C10 C11 122.0(5) . . ?
O1 C11 C10 111.3(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.506
####################################################################### 
# 
# 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_nc8rnb
_database_code_depnum_ccdc_archive 'CCDC 2003256'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2019-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 F O3 S'
_chemical_formula_sum            'C19 H19 F O3 S'
_chemical_formula_weight         346.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H19 O4 S1'
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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1798(3)
_cell_length_b                   8.2382(4)
_cell_length_c                   12.9438(7)
_cell_angle_alpha                88.093(4)
_cell_angle_beta                 81.665(4)
_cell_angle_gamma                73.510(4)
_cell_volume                     827.50(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6654
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8700
_cell_measurement_theta_min      2.5740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12519
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.055
_diffrn_reflns_theta_min         2.578
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  29.00   0.50    1.23    --   10.60 -80.00 -83.00   50
  2  ω     14.00  40.00   0.50    1.23    --   10.60  80.00  39.00   52
  3  ω    -67.00 -42.00   0.50    1.23    --  -10.90 -80.00 -83.00   50
  4  ω     16.00  42.00   0.50    1.23    --  -10.90  80.00  39.00   52
  5  ω     -3.00  72.00   0.50    1.23    --   10.60  82.00 -90.00  150
  6  ω    -16.00  21.00   0.50    1.23    --   10.60  82.00-120.00   74
  7  ω     33.00  70.00   0.50    1.23    --   10.60  82.00-120.00   74
  8  ω      0.00  26.00   0.50    1.23    --   10.60  82.00  90.00   52
  9  ω    -26.00  23.00   0.50    1.23    --   10.60  38.00 120.00   98
 10  ω     71.00 100.00   0.50    1.23    --   10.60  38.00 120.00   58
 11  ω     -7.00  22.00   0.50    1.23    --   10.60  82.00  60.00   58
 12  ω     51.00  97.00   0.50    1.23    --   10.60  82.00  60.00   92
 13  ω    -69.00  35.00   0.50    1.23    --   10.60 -82.00-150.00  208
 14  ω     14.00  75.00   0.50    1.23    --   10.60  77.00 150.00  122
 15  ω    -79.00 -34.00   0.50    1.23    --   10.60 -77.00-180.00   90
 16  ω     -9.00  17.00   0.50    1.23    --   10.60 -77.00-180.00   52
 17  ω    -10.00  38.00   0.50    1.23    --   10.60  82.00   0.00   96
 18  ω     20.00  60.00   0.50    1.23    --  -10.90  77.00 120.00   80
 19  ω    -36.00   2.00   0.50    1.23    --  -10.90  77.00 120.00   76
 20  ω    -96.00   6.00   0.50    1.23    --  -10.90 -82.00  60.00  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0059692000
_diffrn_orient_matrix_UB_12      0.0462940000
_diffrn_orient_matrix_UB_13      0.0438569000
_diffrn_orient_matrix_UB_21      0.0885243000
_diffrn_orient_matrix_UB_22      -0.0105440000
_diffrn_orient_matrix_UB_23      -0.0180642000
_diffrn_orient_matrix_UB_31      -0.0217466000
_diffrn_orient_matrix_UB_32      0.0762156000
_diffrn_orient_matrix_UB_33      -0.0285970000
_diffrn_oxdiff_digest_frames     
;
0187d8a2b1becebaa6ef6818b76f64d4bd00027ada2
;
_diffrn_oxdiff_digest_hkl        
;
0199f794fe159d59089b6d239a6b7ab34893af
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2907
_reflns_number_total             3425
_reflns_odcompleteness_completeness 98.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.060
_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)+(0.0397P)²+0.3883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0971
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.16475(5) 0.69863(5) 0.27068(3) 0.01776(13) Uani 1 1 d . . . . .
F1 F 0.54648(14) 1.01182(13) 0.12062(9) 0.0349(3) Uani 1 1 d . . . . .
O1 O 0.67483(15) 0.57814(16) 0.02759(9) 0.0272(3) Uani 1 1 d . . . . .
O2 O 0.02812(14) 0.71881(15) 0.20791(9) 0.0233(3) Uani 1 1 d . . . . .
O3 O 0.15494(15) 0.83493(14) 0.34087(9) 0.0235(3) Uani 1 1 d . . . . .
C1 C 0.6875(2) 0.7444(2) 0.04688(15) 0.0290(4) Uani 1 1 d . . . . .
H1A H 0.6799 0.8086 -0.0173 0.035 Uiso 1 1 calc R . . . .
H1B H 0.7992 0.7348 0.0675 0.035 Uiso 1 1 calc R . . . .
C2 C 0.5480(2) 0.8399(2) 0.13115(14) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.3707(2) 0.8202(2) 0.12104(14) 0.0214(4) Uani 1 1 d . . . . .
H3A H 0.3596 0.8055 0.0486 0.026 Uiso 1 1 calc R . . . .
H3B H 0.2797 0.9180 0.1499 0.026 Uiso 1 1 calc R . . . .
C4 C 0.36432(19) 0.6592(2) 0.18487(13) 0.0176(3) Uani 1 1 d . . . . .
H4 H 0.3754 0.5653 0.1373 0.021 Uiso 1 1 calc R . . . .
C5 C 0.52098(19) 0.6161(2) 0.24769(13) 0.0184(3) Uani 1 1 d . . . . .
H5 H 0.4817 0.5956 0.3208 0.022 Uiso 1 1 calc R . . . .
C6 C 0.5773(2) 0.7796(2) 0.24024(14) 0.0227(4) Uani 1 1 d . . . . .
H6A H 0.5075 0.8622 0.2923 0.027 Uiso 1 1 calc R . . . .
H6B H 0.6975 0.7569 0.2489 0.027 Uiso 1 1 calc R . . . .
C7 C 0.66048(19) 0.4622(2) 0.20299(13) 0.0194(4) Uani 1 1 d . . . . .
C8 C 0.7174(2) 0.3217(2) 0.26540(14) 0.0231(4) Uani 1 1 d . . . . .
H8 H 0.6707 0.3252 0.3355 0.028 Uiso 1 1 calc R . . . .
C9 C 0.8418(2) 0.1773(2) 0.22550(15) 0.0281(4) Uani 1 1 d . . . . .
H9 H 0.8773 0.0850 0.2684 0.034 Uiso 1 1 calc R . . . .
C10 C 0.9128(2) 0.1709(2) 0.12185(15) 0.0296(4) Uani 1 1 d . . . . .
H10 H 0.9966 0.0744 0.0948 0.036 Uiso 1 1 calc R . . . .
C11 C 0.8591(2) 0.3088(2) 0.05790(14) 0.0280(4) Uani 1 1 d . . . . .
H11 H 0.9070 0.3049 -0.0120 0.034 Uiso 1 1 calc R . . . .
C12 C 0.7339(2) 0.4520(2) 0.09854(13) 0.0229(4) Uani 1 1 d . . . . .
C13 C 0.18417(19) 0.5129(2) 0.34436(13) 0.0178(3) Uani 1 1 d . . . . .
C14 C 0.2188(2) 0.5111(2) 0.44645(13) 0.0220(4) Uani 1 1 d . . . . .
H14 H 0.2271 0.6088 0.4767 0.026 Uiso 1 1 calc R . . . .
C15 C 0.2407(2) 0.3624(2) 0.50265(14) 0.0245(4) Uani 1 1 d . . . . .
H15 H 0.2639 0.3609 0.5710 0.029 Uiso 1 1 calc R . . . .
C16 C 0.2286(2) 0.2150(2) 0.45868(13) 0.0212(4) Uani 1 1 d . . . . .
C17 C 0.1910(2) 0.2206(2) 0.35681(14) 0.0253(4) Uani 1 1 d . . . . .
H17 H 0.1809 0.1235 0.3269 0.030 Uiso 1 1 calc R . . . .
C18 C 0.1685(2) 0.3681(2) 0.29943(14) 0.0234(4) Uani 1 1 d . . . . .
H18 H 0.1431 0.3703 0.2316 0.028 Uiso 1 1 calc R . . . .
C19 C 0.2525(2) 0.0529(2) 0.52006(15) 0.0282(4) Uani 1 1 d . . . . .
H19A H 0.1448 0.0259 0.5344 0.042 Uiso 1 1 calc GR . . . .
H19B H 0.2919 0.0670 0.5846 0.042 Uiso 1 1 calc GR . . . .
H19C H 0.3361 -0.0374 0.4801 0.042 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4441(12) . ?
S1 O3 1.4451(12) . ?
S1 C4 1.7892(16) . ?
S1 C13 1.7566(17) . ?
F1 C2 1.4151(19) . ?
O1 C1 1.435(2) . ?
O1 C12 1.392(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.516(3) . ?
C2 C3 1.529(2) . ?
C2 C6 1.510(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.549(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.566(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.539(2) . ?
C5 C7 1.510(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.396(2) . ?
C7 C12 1.393(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(2) . ?
C13 C14 1.390(2) . ?
C13 C18 1.390(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(2) . ?
C16 C17 1.393(2) . ?
C16 C19 1.510(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
O2 S1 O3 118.16(7) . . ?
O2 S1 C4 108.17(7) . . ?
O2 S1 C13 109.34(7) . . ?
O3 S1 C4 108.04(7) . . ?
O3 S1 C13 107.89(7) . . ?
C13 S1 C4 104.36(7) . . ?
C12 O1 C1 117.49(13) . . ?
O1 C1 H1A 109.0 . . ?
O1 C1 H1B 109.0 . . ?
O1 C1 C2 112.79(14) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
F1 C2 C1 105.87(14) . . ?
F1 C2 C3 110.37(13) . . ?
F1 C2 C6 110.23(14) . . ?
C1 C2 C3 112.76(15) . . ?
C6 C2 C1 113.53(15) . . ?
C6 C2 C3 104.17(13) . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C2 C3 C4 103.67(13) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
S1 C4 H4 109.7 . . ?
C3 C4 S1 109.76(11) . . ?
C3 C4 H4 109.7 . . ?
C3 C4 C5 106.78(12) . . ?
C5 C4 S1 111.17(11) . . ?
C5 C4 H4 109.7 . . ?
C4 C5 H5 109.4 . . ?
C6 C5 C4 103.22(13) . . ?
C6 C5 H5 109.4 . . ?
C7 C5 C4 111.45(13) . . ?
C7 C5 H5 109.4 . . ?
C7 C5 C6 113.67(13) . . ?
C2 C6 C5 102.73(13) . . ?
C2 C6 H6A 111.2 . . ?
C2 C6 H6B 111.2 . . ?
C5 C6 H6A 111.2 . . ?
C5 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C5 120.55(15) . . ?
C12 C7 C5 122.02(15) . . ?
C12 C7 C8 117.41(15) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.62(16) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.74(17) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.97(17) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.76(17) . . ?
C12 C11 H11 120.1 . . ?
O1 C12 C7 121.88(15) . . ?
C11 C12 O1 116.37(15) . . ?
C11 C12 C7 121.50(16) . . ?
C14 C13 S1 119.58(13) . . ?
C14 C13 C18 120.61(16) . . ?
C18 C13 S1 119.79(13) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.26(16) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.15(16) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 118.53(16) . . ?
C15 C16 C19 121.10(16) . . ?
C17 C16 C19 120.35(15) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.17(16) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 H18 120.4 . . ?
C17 C18 C13 119.26(16) . . ?
C17 C18 H18 120.4 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
S1 C4 C5 C6 -104.59(13) . . . . ?
S1 C4 C5 C7 133.04(12) . . . . ?
S1 C13 C14 C15 -177.45(12) . . . . ?
S1 C13 C18 C17 177.37(13) . . . . ?
F1 C2 C3 C4 -153.22(14) . . . . ?
F1 C2 C6 C5 163.49(13) . . . . ?
O1 C1 C2 F1 -163.78(13) . . . . ?
O1 C1 C2 C3 -43.0(2) . . . . ?
O1 C1 C2 C6 75.17(18) . . . . ?
O2 S1 C4 C3 68.33(12) . . . . ?
O2 S1 C4 C5 -173.76(10) . . . . ?
O2 S1 C13 C14 -141.34(13) . . . . ?
O2 S1 C13 C18 40.03(15) . . . . ?
O3 S1 C4 C3 -60.67(13) . . . . ?
O3 S1 C4 C5 57.24(13) . . . . ?
O3 S1 C13 C14 -11.63(15) . . . . ?
O3 S1 C13 C18 169.74(12) . . . . ?
C1 O1 C12 C7 62.0(2) . . . . ?
C1 O1 C12 C11 -123.67(17) . . . . ?
C1 C2 C3 C4 88.61(16) . . . . ?
C1 C2 C6 C5 -77.93(16) . . . . ?
C2 C3 C4 S1 132.27(12) . . . . ?
C2 C3 C4 C5 11.67(17) . . . . ?
C3 C2 C6 C5 45.09(16) . . . . ?
C3 C4 C5 C6 15.10(16) . . . . ?
C3 C4 C5 C7 -107.27(15) . . . . ?
C4 S1 C13 C14 103.12(14) . . . . ?
C4 S1 C13 C18 -75.51(14) . . . . ?
C4 C5 C6 C2 -36.49(16) . . . . ?
C4 C5 C7 C8 -122.98(16) . . . . ?
C4 C5 C7 C12 55.3(2) . . . . ?
C5 C7 C8 C9 178.21(15) . . . . ?
C5 C7 C12 O1 -4.5(2) . . . . ?
C5 C7 C12 C11 -178.58(15) . . . . ?
C6 C2 C3 C4 -34.92(17) . . . . ?
C6 C5 C7 C8 120.88(17) . . . . ?
C6 C5 C7 C12 -60.9(2) . . . . ?
C7 C5 C6 C2 84.38(16) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C7 C12 O1 173.79(15) . . . . ?
C8 C7 C12 C11 -0.3(2) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 O1 -173.94(15) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C12 O1 C1 C2 -77.77(18) . . . . ?
C12 C7 C8 C9 -0.1(2) . . . . ?
C13 S1 C4 C3 -175.31(11) . . . . ?
C13 S1 C4 C5 -57.40(13) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C13 C18 C17 -1.2(2) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C14 C15 C16 C19 -179.98(15) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C18 C13 C14 C15 1.2(2) . . . . ?
C19 C16 C17 C18 179.92(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.526
_oxdiff_exptl_absorpt_empirical_full_min 0.726
####################################################################### 
# 
# 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_nc1202nb
_database_code_depnum_ccdc_archive 'CCDC 2003262'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2020-03-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H17 F O3 S'
_chemical_formula_sum            'C18 H17 F O3 S'
_chemical_formula_weight         332.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H17 S1 O3 F1'
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'
F F 0.0171 0.0103 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.87130(10)
_cell_length_b                   10.4176(3)
_cell_length_c                   11.8932(3)
_cell_angle_alpha                99.558(2)
_cell_angle_beta                 105.692(2)
_cell_angle_gamma                96.770(2)
_cell_volume                     796.26(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7422
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9860
_cell_measurement_theta_min      2.0070
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12550
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.82
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00 -20.00   0.50    7.15    --   10.60 -80.00  42.00   50
  2  ω     42.00  67.00   0.50    7.15    --   10.60  80.00 165.00   50
  3  ω      1.00  27.00   0.50    7.15    --   10.60  80.00 165.00   52
  4  ω    -67.00 -42.00   0.50    7.15    --  -10.90 -80.00  42.00   50
  5  ω      7.00  35.00   0.50    7.15    --   10.60 -77.00 -60.00   56
  6  ω    -62.00 -36.00   0.50    7.15    --   10.60 -77.00 -30.00   52
  7  ω    -12.00  14.00   0.50    7.15    --   10.60 -82.00  30.00   52
  8  ω    -16.00  99.00   0.50    7.15    --   10.60  82.00 -90.00  230
  9  ω    -78.00  36.00   0.50    7.15    --   10.60 -77.00  90.00  228
 10  ω    -17.00  71.00   0.50    7.15    --   10.60  82.00  30.00  176
 11  ω    -21.00  17.00   0.50    7.15    --   10.60 -77.00 -30.00   76
 12  ω    -14.00  11.00   0.50    7.15    --   10.60  82.00  90.00   50
 13  ω    -79.00 -51.00   0.50    7.15    --   10.60 -82.00  30.00   56
 14  ω    -72.00 -46.00   0.50    7.15    --   10.60 -77.00 -60.00   52
 15  ω    -25.00  17.00   0.50    7.15    --  -10.90 -82.00   0.00   84
 16  ω    -97.00   7.00   0.50    7.15    --  -10.90 -77.00-180.00  208
 17  ω    -64.00 -38.00   0.50    7.15    --  -10.90 -82.00   0.00   52
 18  ω    -74.00   4.00   0.50    7.15    --  -10.90 -82.00 120.00  156
 19  ω    -99.00 -65.00   0.50    7.15    --  -10.90 -77.00 -90.00   68
 20  ω     22.00  54.00   0.50    7.15    --  -10.90  80.00 165.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0350148000
_diffrn_orient_matrix_UB_12      -0.0611336000
_diffrn_orient_matrix_UB_13      0.0128733000
_diffrn_orient_matrix_UB_21      0.0163275000
_diffrn_orient_matrix_UB_22      -0.0341614000
_diffrn_orient_matrix_UB_23      -0.0525344000
_diffrn_orient_matrix_UB_31      0.1017463000
_diffrn_orient_matrix_UB_32      -0.0027018000
_diffrn_orient_matrix_UB_33      0.0329211000
_diffrn_oxdiff_digest_frames     
;
01542d3b515a656385ac5f93c1b47053d800025873e
;
_diffrn_oxdiff_digest_hkl        
;
011ee2d9e15e2f0085946a79a690dcb258a77e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_number_gt                2712
_reflns_number_total             3134
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0461P)²+0.5397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1059
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.72712(7) 0.59123(4) 0.90141(4) 0.02396(14) Uani 1 d . . .
F1 F 0.2892(2) 1.02809(12) 0.81327(13) 0.0481(4) Uani 1 d . . .
O1 O 0.5993(2) 0.16954(12) 0.63418(12) 0.0270(3) Uani 1 d . . .
O2 O 0.9231(2) 0.62531(13) 0.88278(14) 0.0337(4) Uani 1 d . . .
O3 O 0.7229(2) 0.57377(12) 1.01818(12) 0.0288(3) Uani 1 d . . .
C1 C 0.4239(3) 0.20929(18) 0.57378(17) 0.0245(4) Uani 1 d . . .
C2 C 0.4025(3) 0.34197(18) 0.58701(17) 0.0249(4) Uani 1 d . . .
C3 C 0.2196(3) 0.3736(2) 0.52195(18) 0.0300(5) Uani 1 d . . .
H3 H 0.2018 0.4634 0.5310 0.036 Uiso 1 calc . . R
C4 C 0.0642(3) 0.2777(2) 0.44493(18) 0.0317(5) Uani 1 d . . .
H4 H -0.0584 0.3012 0.4002 0.038 Uiso 1 calc . . R
C5 C 0.0884(3) 0.1453(2) 0.43312(19) 0.0335(5) Uani 1 d . . .
H5 H -0.0185 0.0784 0.3805 0.040 Uiso 1 calc . . R
C6 C 0.2677(3) 0.11119(19) 0.49791(18) 0.0301(5) Uani 1 d . . .
H6 H 0.2835 0.0211 0.4904 0.036 Uiso 1 calc . . R
C7 C 0.7633(3) 0.27281(17) 0.71672(17) 0.0237(4) Uani 1 d . . .
C8 C 0.6968(3) 0.32326(17) 0.82719(18) 0.0254(4) Uani 1 d . . .
H8A H 0.8175 0.3525 0.8989 0.030 Uiso 1 calc . . R
H8B H 0.6019 0.2530 0.8416 0.030 Uiso 1 calc . . R
C9 C 0.5870(3) 0.44160(17) 0.79798(17) 0.0228(4) Uani 1 d . . .
H9 H 0.4439 0.4248 0.8034 0.027 Uiso 1 calc . . R
C10 C 0.5820(3) 0.44390(18) 0.66821(18) 0.0260(4) Uani 1 d . . .
H10 H 0.5779 0.5339 0.6497 0.031 Uiso 1 calc . . R
C11 C 0.7789(3) 0.39236(19) 0.6596(2) 0.0295(5) Uani 1 d . . .
H11A H 0.7789 0.3668 0.5756 0.035 Uiso 1 calc . . R
H11B H 0.9030 0.4583 0.7049 0.035 Uiso 1 calc . . R
C12 C 0.9510(3) 0.20763(19) 0.74199(19) 0.0309(5) Uani 1 d . . .
H12A H 0.9235 0.1302 0.7757 0.046 Uiso 1 calc . . GR
H12B H 1.0669 0.2704 0.7991 0.046 Uiso 1 calc . . GR
H12C H 0.9845 0.1800 0.6676 0.046 Uiso 1 calc . . GR
C13 C 0.5833(3) 0.71630(17) 0.86363(17) 0.0223(4) Uani 1 d . . .
C14 C 0.4096(3) 0.72473(18) 0.90010(17) 0.0258(4) Uani 1 d . . .
H14 H 0.3606 0.6588 0.9370 0.031 Uiso 1 calc . . R
C15 C 0.3077(3) 0.8303(2) 0.88234(19) 0.0311(5) Uani 1 d . . .
H15 H 0.1887 0.8388 0.9072 0.037 Uiso 1 calc . . R
C16 C 0.3839(3) 0.92224(18) 0.8277(2) 0.0323(5) Uani 1 d . . .
C17 C 0.5488(3) 0.9116(2) 0.7835(2) 0.0381(5) Uani 1 d . . .
H17 H 0.5908 0.9742 0.7414 0.046 Uiso 1 calc . . R
C18 C 0.6512(3) 0.8067(2) 0.8027(2) 0.0340(5) Uani 1 d . . .
H18 H 0.7665 0.7965 0.7745 0.041 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4364(14) . ?
S1 O3 1.4378(15) . ?
S1 C9 1.7996(19) . ?
S1 C13 1.7702(18) . ?
F1 C16 1.357(2) . ?
O1 C1 1.374(2) . ?
O1 C7 1.468(2) . ?
C1 C2 1.395(3) . ?
C1 C6 1.386(3) . ?
C2 C3 1.394(3) . ?
C2 C10 1.512(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.537(3) . ?
C7 C11 1.521(3) . ?
C7 C12 1.510(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.559(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.539(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.535(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.383(3) . ?
C13 C18 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.374(3) . ?
C16 C17 1.380(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9500 . ?

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
O2 S1 O3 118.25(9) . . ?
O2 S1 C9 109.99(9) . . ?
O2 S1 C13 107.28(8) . . ?
O3 S1 C9 106.81(8) . . ?
O3 S1 C13 108.21(8) . . ?
C13 S1 C9 105.60(9) . . ?
C1 O1 C7 117.14(14) . . ?
O1 C1 C2 122.04(18) . . ?
O1 C1 C6 116.94(16) . . ?
C6 C1 C2 121.02(18) . . ?
C1 C2 C10 118.08(17) . . ?
C3 C2 C1 118.24(19) . . ?
C3 C2 C10 123.65(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.50(18) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.38(19) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.63(18) . . ?
C5 C6 H6 120.2 . . ?
O1 C7 C8 108.83(15) . . ?
O1 C7 C11 108.58(16) . . ?
O1 C7 C12 104.84(14) . . ?
C11 C7 C8 103.88(14) . . ?
C12 C7 C8 114.62(16) . . ?
C12 C7 C11 115.90(16) . . ?
C7 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C7 C8 C9 105.39(15) . . ?
H8A C8 H8B 108.8 . . ?
C9 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
S1 C9 H9 109.8 . . ?
C8 C9 S1 109.73(13) . . ?
C8 C9 H9 109.8 . . ?
C10 C9 S1 113.02(12) . . ?
C10 C9 C8 104.45(14) . . ?
C10 C9 H9 109.8 . . ?
C2 C10 C9 107.89(15) . . ?
C2 C10 H10 112.8 . . ?
C2 C10 C11 107.36(15) . . ?
C9 C10 H10 112.8 . . ?
C11 C10 C9 102.68(15) . . ?
C11 C10 H10 112.8 . . ?
C7 C11 C10 100.72(15) . . ?
C7 C11 H11A 111.6 . . ?
C7 C11 H11B 111.6 . . ?
C10 C11 H11A 111.6 . . ?
C10 C11 H11B 111.6 . . ?
H11A C11 H11B 109.4 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 S1 118.71(14) . . ?
C14 C13 C18 121.56(17) . . ?
C18 C13 S1 119.67(15) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.38(18) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 117.98(19) . . ?
C16 C15 H15 121.0 . . ?
F1 C16 C15 118.44(19) . . ?
F1 C16 C17 117.81(19) . . ?
C15 C16 C17 123.73(18) . . ?
C16 C17 H17 121.1 . . ?
C16 C17 C18 117.88(19) . . ?
C18 C17 H17 121.1 . . ?
C13 C18 H18 120.4 . . ?
C17 C18 C13 119.23(19) . . ?
C17 C18 H18 120.4 . . ?

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 C9 C10 C2 -159.14(12) . . . . ?
S1 C9 C10 C11 87.65(15) . . . . ?
S1 C13 C14 C15 173.22(15) . . . . ?
S1 C13 C18 C17 -173.87(17) . . . . ?
F1 C16 C17 C18 177.29(19) . . . . ?
O1 C1 C2 C3 179.75(17) . . . . ?
O1 C1 C2 C10 1.7(3) . . . . ?
O1 C1 C6 C5 -178.96(18) . . . . ?
O1 C7 C8 C9 -91.05(16) . . . . ?
O1 C7 C11 C10 71.74(18) . . . . ?
O2 S1 C9 C8 66.92(14) . . . . ?
O2 S1 C9 C10 -49.21(15) . . . . ?
O2 S1 C13 C14 -164.69(15) . . . . ?
O2 S1 C13 C18 12.72(19) . . . . ?
O3 S1 C9 C8 -62.59(14) . . . . ?
O3 S1 C9 C10 -178.71(12) . . . . ?
O3 S1 C13 C14 -36.07(18) . . . . ?
O3 S1 C13 C18 141.34(17) . . . . ?
C1 O1 C7 C8 72.18(19) . . . . ?
C1 O1 C7 C11 -40.3(2) . . . . ?
C1 O1 C7 C12 -164.74(16) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C10 C9 -77.0(2) . . . . ?
C1 C2 C10 C11 33.1(2) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C2 C10 C11 C7 -66.78(18) . . . . ?
C3 C2 C10 C9 105.0(2) . . . . ?
C3 C2 C10 C11 -144.92(19) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C1 C2 C10 -178.01(17) . . . . ?
C7 O1 C1 C2 1.7(2) . . . . ?
C7 O1 C1 C6 -178.65(16) . . . . ?
C7 C8 C9 S1 -116.87(14) . . . . ?
C7 C8 C9 C10 4.56(19) . . . . ?
C8 C7 C11 C10 -43.97(19) . . . . ?
C8 C9 C10 C2 81.64(17) . . . . ?
C8 C9 C10 C11 -31.57(18) . . . . ?
C9 S1 C13 C14 78.01(17) . . . . ?
C9 S1 C13 C18 -104.58(18) . . . . ?
C9 C10 C11 C7 46.81(18) . . . . ?
C10 C2 C3 C4 176.92(17) . . . . ?
C11 C7 C8 C9 24.48(19) . . . . ?
C12 C7 C8 C9 151.95(16) . . . . ?
C12 C7 C11 C10 -170.64(16) . . . . ?
C13 S1 C9 C8 -177.63(12) . . . . ?
C13 S1 C9 C10 66.24(15) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C13 C18 C17 3.5(3) . . . . ?
C14 C15 C16 F1 -177.96(17) . . . . ?
C14 C15 C16 C17 3.8(3) . . . . ?
C15 C16 C17 C18 -4.5(3) . . . . ?
C16 C17 C18 C13 0.8(3) . . . . ?
C18 C13 C14 C15 -4.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.580
_oxdiff_exptl_absorpt_empirical_full_min 0.735
####################################################################### 
# 
# 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_nc1204nb
_database_code_depnum_ccdc_archive 'CCDC 2003258'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 F2 O3 S'
_chemical_formula_sum            'C19 H18 F2 O3 S'
_chemical_formula_weight         364.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H18 F2 O3 S1'
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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.88630(10)
_cell_length_b                   9.4890(2)
_cell_length_c                   29.6414(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1655.62(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19556
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9770
_cell_measurement_theta_min      2.2460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            31130
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.254
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
; 
List of Runs (angles in degrees, time in seconds): 
  
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames 
#-------------------------------------------------------------------------- 
  1  ω    -16.00  23.00   0.50    3.05    --   10.60  -8.00 145.00   78 
  2  ω     26.00  53.00   0.50    3.05    --  -10.90  -8.00 145.00   54 
  3  ω    -21.00   5.00   0.50    3.05    --  -10.90   8.00 -40.00   52 
  4  ω    -86.00 -60.00   0.50    3.05    --  -10.90  -8.00 145.00   52 
  5  ω     -1.00  98.00   0.50    3.05    --   10.60  82.00  30.00  198 
  6  ω     49.00  75.00   0.50    3.05    --   10.60  77.00-120.00   52 
  7  ω     26.00  51.00   0.50    3.05    --   10.60  77.00  60.00   50 
  8  ω    -14.00  11.00   0.50    3.05    --   10.60   8.00 -40.00   50 
  9  ω    -10.00  52.00   0.50    3.05    --   10.60  82.00-180.00  124 
 10  ω     28.00  67.00   0.50    3.05    --   10.60  82.00 150.00   78 
 11  ω     -5.00  39.00   0.50    3.05    --   10.60  82.00   0.00   88 
 12  ω     -5.00 100.00   0.50    3.05    --   10.60  82.00 -60.00  210 
 13  ω    -17.00  40.00   0.50    3.05    --   10.60  82.00-120.00  114 
 14  ω    -17.00  38.00   0.50    3.05    --   10.60  82.00  90.00  110 
 15  ω    -74.00 -48.00   0.50    3.05    --   10.60 -77.00-150.00   52 
 16  ω    -30.00  -5.00   0.50    3.05    --   10.60 -77.00-150.00   50 
 17  ω     21.00  46.00   0.50    3.05    --   10.60  77.00   0.00   50 
 18  ω    -36.00  79.00   0.50    3.05    --  -10.90  82.00 -30.00  230 
 19  ω   -100.00 -44.00   0.50    3.05    --  -10.90 -82.00 150.00  112 
 20  ω    -29.00  79.00   0.50    3.05    --  -10.90  77.00-120.00  216 
 21  ω    -86.00  -9.00   0.50    3.05    --  -10.90 -77.00  90.00  154 
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0575240000
_diffrn_orient_matrix_UB_12      -0.0654078000
_diffrn_orient_matrix_UB_13      -0.0017093000
_diffrn_orient_matrix_UB_21      -0.1057599000
_diffrn_orient_matrix_UB_22      -0.0352673000
_diffrn_orient_matrix_UB_23      -0.0020853000
_diffrn_orient_matrix_UB_31      0.0050766000
_diffrn_orient_matrix_UB_32      0.0077708000
_diffrn_orient_matrix_UB_33      -0.0237887000
_diffrn_oxdiff_digest_frames     
; 
015b094a7991dd23a321443653c4a036bc00025941b 
;
_diffrn_oxdiff_digest_hkl        
; 
0156f760f6395405aee6967eebea7ff7d1ed06 
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                3349
_reflns_number_total             3504
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1313 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     115
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+0.8298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0780
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2. Rigid bond restraints 
 F1, C2 
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 8 
3. Uiso/Uaniso restraints and constraints 
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim 
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) 
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, 
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) 
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, 
Uanis(C19) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001 
4.a Ternary CH refined with riding coordinates: 
 C4(H4), C5(H5) 
4.b Secondary CH2 refined with riding coordinates: 
 C1(H1A,H1B), C3(H3A,H3B), C12(H12A,H12B) 
4.c Aromatic/amide H refined with riding coordinates: 
 C7(H7), C9(H9), C10(H10), C14(H14), C15(H15), C17(H17), C18(H18) 
4.d Idealised Me refined as rotating group: 
 C19(H19A,H19B,H19C) 
;
_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 0.66647(10) 0.58934(6) 0.34036(2) 0.01759(14) Uani 1 1 d . . . . .
F1 F 0.4642(2) 0.13045(15) 0.38980(5) 0.0226(3) Uani 1 1 d . U . . .
F2 F 0.8045(3) 0.70257(16) 0.56977(5) 0.0334(4) Uani 1 1 d . . . . .
O1 O 0.2255(3) 0.40281(17) 0.46143(6) 0.0186(3) Uani 1 1 d . . . . .
O2 O 0.7367(3) 0.72876(19) 0.35368(6) 0.0263(4) Uani 1 1 d . . . . .
O3 O 0.8388(3) 0.48859(18) 0.32761(6) 0.0234(4) Uani 1 1 d . . . . .
C1 C 0.2990(4) 0.2652(2) 0.44742(8) 0.0178(5) Uani 1 1 d . U . . .
H1A H 0.1644 0.2084 0.4390 0.021 Uiso 1 1 calc R . . . .
H1B H 0.3747 0.2177 0.4731 0.021 Uiso 1 1 calc R . . . .
C2 C 0.4624(4) 0.2705(2) 0.40753(8) 0.0171(5) Uani 1 1 d . U . . .
C3 C 0.3896(4) 0.3766(2) 0.37155(8) 0.0169(5) Uani 1 1 d . U . . .
H3A H 0.2224 0.3874 0.3711 0.020 Uiso 1 1 calc R . . . .
H3B H 0.4418 0.3467 0.3413 0.020 Uiso 1 1 calc R . . . .
C4 C 0.5055(4) 0.5147(2) 0.38589(7) 0.0154(5) Uani 1 1 d . U . . .
H4 H 0.3895 0.5837 0.3968 0.019 Uiso 1 1 calc R . . . .
C5 C 0.6759(4) 0.4775(2) 0.42487(7) 0.0152(4) Uani 1 1 d . U . . .
H5 H 0.8255 0.5238 0.4189 0.018 Uiso 1 1 calc R . . . .
C6 C 0.5916(4) 0.5189(2) 0.47105(8) 0.0154(5) Uani 1 1 d . U . . .
C7 C 0.7334(4) 0.5961(3) 0.49964(8) 0.0186(5) Uani 1 1 d . U . . .
H7 H 0.8792 0.6254 0.4896 0.022 Uiso 1 1 calc R . . . .
C8 C 0.6599(5) 0.6295(2) 0.54264(8) 0.0211(5) Uani 1 1 d . U . . .
C9 C 0.4492(4) 0.5940(3) 0.55881(8) 0.0217(5) Uani 1 1 d . U . . .
H9 H 0.4020 0.6209 0.5882 0.026 Uiso 1 1 calc R . . . .
C10 C 0.3079(4) 0.5175(2) 0.53062(8) 0.0204(5) Uani 1 1 d . U . . .
H10 H 0.1607 0.4914 0.5408 0.024 Uiso 1 1 calc R . . . .
C11 C 0.3786(4) 0.4785(2) 0.48769(8) 0.0158(5) Uani 1 1 d . U . . .
C12 C 0.7009(4) 0.3166(2) 0.41991(8) 0.0169(5) Uani 1 1 d . U . . .
H12A H 0.8105 0.2923 0.3958 0.020 Uiso 1 1 calc R . . . .
H12B H 0.7509 0.2728 0.4486 0.020 Uiso 1 1 calc R . . . .
C13 C 0.4686(4) 0.6026(3) 0.29606(8) 0.0180(5) Uani 1 1 d . U . . .
C14 C 0.2948(4) 0.7016(3) 0.29820(9) 0.0232(5) Uani 1 1 d . U . . .
H14 H 0.2830 0.7635 0.3233 0.028 Uiso 1 1 calc R . . . .
C15 C 0.1392(5) 0.7084(3) 0.26325(9) 0.0271(6) Uani 1 1 d . U . . .
H15 H 0.0201 0.7758 0.2646 0.033 Uiso 1 1 calc R . . . .
C16 C 0.1536(5) 0.6186(3) 0.22624(9) 0.0270(6) Uani 1 1 d . U . . .
C17 C 0.3278(5) 0.5198(3) 0.22497(9) 0.0291(6) Uani 1 1 d . U . . .
H17 H 0.3394 0.4577 0.2000 0.035 Uiso 1 1 calc R . . . .
C18 C 0.4851(5) 0.5106(3) 0.25974(9) 0.0255(6) Uani 1 1 d . U . . .
H18 H 0.6028 0.4422 0.2587 0.031 Uiso 1 1 calc R . . . .
C19 C -0.0162(5) 0.6270(4) 0.18849(11) 0.0392(7) Uani 1 1 d . U . . .
H19A H -0.0360 0.7255 0.1794 0.059 Uiso 1 1 calc GR . . . .
H19B H -0.1621 0.5888 0.1987 0.059 Uiso 1 1 calc GR . . . .
H19C H 0.0387 0.5720 0.1627 0.059 Uiso 1 1 calc GR . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4411(18) . ?
S1 O3 1.4441(18) . ?
S1 C4 1.794(2) . ?
S1 C13 1.760(2) . ?
F1 C2 1.429(3) . ?
F2 C8 1.361(3) . ?
O1 C1 1.437(3) . ?
O1 C11 1.390(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.525(3) . ?
C2 C3 1.528(3) . ?
C2 C12 1.516(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.537(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.570(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.508(3) . ?
C5 C12 1.541(3) . ?
C6 C7 1.397(3) . ?
C6 C11 1.401(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(3) . ?
C8 C9 1.372(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.390(3) . ?
C13 C18 1.389(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(4) . ?
C16 C17 1.390(4) . ?
C16 C19 1.502(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(4) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
O2 S1 O3 118.56(11) . . ?
O2 S1 C4 107.93(11) . . ?
O2 S1 C13 109.19(11) . . ?
O3 S1 C4 107.83(11) . . ?
O3 S1 C13 108.47(11) . . ?
C13 S1 C4 103.88(11) . . ?
C11 O1 C1 115.86(17) . . ?
O1 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
O1 C1 C2 112.57(18) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
F1 C2 C1 105.02(18) . . ?
F1 C2 C3 110.98(18) . . ?
F1 C2 C12 110.50(18) . . ?
C1 C2 C3 112.72(19) . . ?
C12 C2 C1 114.0(2) . . ?
C12 C2 C3 103.80(19) . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
C2 C3 C4 104.14(18) . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
S1 C4 H4 110.2 . . ?
C3 C4 S1 111.28(16) . . ?
C3 C4 H4 110.2 . . ?
C3 C4 C5 107.17(18) . . ?
C5 C4 S1 107.76(15) . . ?
C5 C4 H4 110.2 . . ?
C4 C5 H5 109.5 . . ?
C6 C5 C4 113.55(19) . . ?
C6 C5 H5 109.5 . . ?
C6 C5 C12 112.11(19) . . ?
C12 C5 C4 102.33(18) . . ?
C12 C5 H5 109.5 . . ?
C7 C6 C5 119.4(2) . . ?
C7 C6 C11 117.7(2) . . ?
C11 C6 C5 122.8(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.5(2) . . ?
C8 C7 H7 120.2 . . ?
F2 C8 C7 117.8(2) . . ?
F2 C8 C9 118.9(2) . . ?
C9 C8 C7 123.3(2) . . ?
C8 C9 H9 121.3 . . ?
C8 C9 C10 117.4(2) . . ?
C10 C9 H9 121.3 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
O1 C11 C6 121.6(2) . . ?
C10 C11 O1 117.2(2) . . ?
C10 C11 C6 121.2(2) . . ?
C2 C12 C5 102.73(18) . . ?
C2 C12 H12A 111.2 . . ?
C2 C12 H12B 111.2 . . ?
C5 C12 H12A 111.2 . . ?
C5 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
C14 C13 S1 120.09(19) . . ?
C18 C13 S1 119.16(19) . . ?
C18 C13 C14 120.7(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(3) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C19 120.9(3) . . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 C19 120.4(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 H18 120.4 . . ?
C17 C18 C13 119.3(2) . . ?
C17 C18 H18 120.4 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
; 
Empirical correction (ABSPACK) includes: 
- Absorption correction using spherical harmonics 
- Frame scaling 
;
_oxdiff_exptl_absorpt_empirical_full_max 1.897
_oxdiff_exptl_absorpt_empirical_full_min 0.701
####################################################################### 
# 
# 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_nco115nb
_database_code_depnum_ccdc_archive 'CCDC 2003259'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-05-11 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2020-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H18 Cl F O3 S'
_chemical_formula_sum            'C19 H18 Cl F O3 S'
_chemical_formula_weight         380.84
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H18 O3 Cl1 F1 S1'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   14.9529(3)
_cell_length_b                   7.52540(10)
_cell_length_c                   15.8144(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.409(2)
_cell_angle_gamma                90.00
_cell_volume                     1707.06(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18945
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9380
_cell_measurement_theta_min      2.6480
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.36a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31146
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.66
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00   7.00   0.50    3.66    --   10.60 -79.00 -30.00   86
  2  ω     16.00  99.00   0.50    3.66    --   10.60  79.00  93.00  166
  3  ω    -43.00 -13.00   0.50    3.66    --  -10.90 -79.00 -30.00   60
  4  ω    -31.00  -6.00   0.50    3.66    --  -10.90  79.00  93.00   50
  5  ω     -3.00  23.00   0.50    3.66    --   10.60  82.00-180.00   52
  6  ω    -77.00 -51.00   0.50    3.66    --   10.60 -77.00   0.00   52
  7  ω     19.00 100.00   0.50    3.66    --   10.60  77.00-150.00  162
  8  ω     -9.00  37.00   0.50    3.66    --   10.60  82.00-120.00   92
  9  ω    -17.00 100.00   0.50    3.66    --   10.60  82.00 150.00  234
 10  ω     23.00  48.00   0.50    3.66    --   10.60  77.00 -90.00   50
 11  ω     19.00  91.00   0.50    3.66    --   10.60  82.00   0.00  144
 12  ω    -17.00 100.00   0.50    3.66    --   10.60  82.00  60.00  234
 13  ω    -50.00 -21.00   0.50    3.66    --  -10.90 -82.00 -90.00   58
 14  ω     54.00  79.00   0.50    3.66    --  -10.90  77.00 120.00   50
 15  ω    -33.00  -8.00   0.50    3.66    --  -10.90  57.00  60.00   50
 16  ω    -34.00  -8.00   0.50    3.66    --  -10.90  77.00 120.00   52
 17  ω    -31.00  79.00   0.50    3.66    --  -10.90  77.00  30.00  220
 18  ω    -14.00  17.00   0.50    3.66    --  -10.90 -82.00 -90.00   62
 19  ω    -33.00  53.00   0.50    3.66    --  -10.90  77.00 -60.00  172
 20  ω     22.00  72.00   0.50    3.66    --  -10.90  57.00  60.00  100
 21  ω    -50.00   8.00   0.50    3.66    --  -10.90 -77.00-150.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0393438000
_diffrn_orient_matrix_UB_12      -0.0294666000
_diffrn_orient_matrix_UB_13      -0.0337832000
_diffrn_orient_matrix_UB_21      0.0298885000
_diffrn_orient_matrix_UB_22      -0.0448796000
_diffrn_orient_matrix_UB_23      -0.0206734000
_diffrn_orient_matrix_UB_31      -0.0023312000
_diffrn_orient_matrix_UB_32      -0.0773961000
_diffrn_orient_matrix_UB_33      0.0248753000
_diffrn_oxdiff_digest_frames     
;
017417dda8dd145a762ff1d34b10eab0d4000253299
;
_diffrn_oxdiff_digest_hkl        
;
01b0e261cff2fff9c603219d8776f85245c412
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_number_gt                3062
_reflns_number_total             3362
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.36a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0338P)²+1.1332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0799
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.33207(3) 1.02666(6) 0.08997(3) 0.03320(13) Uani 1 d . . .
S1 S 0.81880(3) 0.87843(5) 0.23854(2) 0.01919(11) Uani 1 d . . .
F1 F 0.76035(7) 0.34226(15) 0.06076(7) 0.0352(3) Uani 1 d . . .
O1 O 0.59167(8) 0.42641(15) 0.18304(8) 0.0279(3) Uani 1 d . . .
O2 O 0.76810(8) 1.03451(15) 0.25123(7) 0.0251(3) Uani 1 d . . .
O3 O 0.87000(8) 0.88387(16) 0.17386(7) 0.0281(3) Uani 1 d . . .
C1 C 0.53242(11) 0.5694(2) 0.15735(10) 0.0219(3) Uani 1 d . . .
C2 C 0.44320(12) 0.5527(2) 0.16680(10) 0.0262(4) Uani 1 d . . .
H2 H 0.4249 0.4439 0.1874 0.031 Uiso 1 calc . . R
C3 C 0.38103(12) 0.6920(2) 0.14664(10) 0.0257(4) Uani 1 d . . .
H3 H 0.3199 0.6804 0.1529 0.031 Uiso 1 calc . . R
C4 C 0.40971(11) 0.8492(2) 0.11705(10) 0.0228(3) Uani 1 d . . .
C5 C 0.49893(11) 0.8694(2) 0.10876(10) 0.0195(3) Uani 1 d . . .
H5 H 0.5169 0.9791 0.0888 0.023 Uiso 1 calc . . R
C6 C 0.56232(11) 0.7297(2) 0.12957(9) 0.0185(3) Uani 1 d . . .
C7 C 0.66014(11) 0.7540(2) 0.12259(10) 0.0191(3) Uani 1 d . . .
H7 H 0.6694 0.8802 0.1072 0.023 Uiso 1 calc . . R
C8 C 0.73555(11) 0.7022(2) 0.21059(10) 0.0199(3) Uani 1 d . . .
H8 H 0.7048 0.6875 0.2587 0.024 Uiso 1 calc . . R
C9 C 0.77783(12) 0.5235(2) 0.19403(11) 0.0270(4) Uani 1 d . . .
H9A H 0.8420 0.5396 0.1894 0.032 Uiso 1 calc . . R
H9B H 0.7792 0.4379 0.2419 0.032 Uiso 1 calc . . R
C10 C 0.71235(12) 0.4599(2) 0.10653(11) 0.0280(4) Uani 1 d . . .
C11 C 0.63173(13) 0.3509(2) 0.11905(12) 0.0312(4) Uani 1 d . . .
H11A H 0.5830 0.3415 0.0619 0.037 Uiso 1 calc . . R
H11B H 0.6540 0.2294 0.1378 0.037 Uiso 1 calc . . R
C12 C 0.68315(12) 0.6294(2) 0.05474(11) 0.0247(4) Uani 1 d . . .
H12A H 0.6279 0.6096 0.0037 0.030 Uiso 1 calc . . R
H12B H 0.7345 0.6778 0.0335 0.030 Uiso 1 calc . . R
C13 C 0.89574(10) 0.8182(2) 0.34072(10) 0.0184(3) Uani 1 d . . .
C14 C 0.86882(11) 0.8455(2) 0.41731(10) 0.0206(3) Uani 1 d . . .
H14 H 0.8095 0.8947 0.4142 0.025 Uiso 1 calc . . R
C15 C 0.92988(11) 0.8001(2) 0.49777(10) 0.0231(3) Uani 1 d . . .
H15 H 0.9119 0.8179 0.5501 0.028 Uiso 1 calc . . R
C16 C 1.01732(11) 0.7286(2) 0.50343(11) 0.0233(3) Uani 1 d . . .
C17 C 1.04202(11) 0.7017(2) 0.42598(12) 0.0272(4) Uani 1 d . . .
H17 H 1.1012 0.6518 0.4289 0.033 Uiso 1 calc . . R
C18 C 0.98216(11) 0.7462(2) 0.34481(11) 0.0246(4) Uani 1 d . . .
H18 H 1.0001 0.7277 0.2924 0.030 Uiso 1 calc . . R
C19 C 1.08373(13) 0.6836(2) 0.59159(12) 0.0321(4) Uani 1 d . . .
H19A H 1.1291 0.7799 0.6103 0.048 Uiso 1 calc . . GR
H19B H 1.1165 0.5729 0.5868 0.048 Uiso 1 calc . . GR
H19C H 1.0488 0.6688 0.6351 0.048 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.7417(17) . ?
S1 O2 1.4424(12) . ?
S1 O3 1.4410(11) . ?
S1 C8 1.7869(16) . ?
S1 C13 1.7578(16) . ?
F1 C10 1.4547(19) . ?
O1 C1 1.3802(19) . ?
O1 C11 1.431(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.399(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(2) . ?
C4 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C6 C7 1.509(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.573(2) . ?
C7 C12 1.535(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.540(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.529(2) . ?
C10 C11 1.516(3) . ?
C10 C12 1.513(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.395(2) . ?
C13 C18 1.386(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.393(2) . ?
C16 C17 1.390(2) . ?
C16 C19 1.504(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
O2 S1 C8 106.38(7) . . ?
O2 S1 C13 108.37(7) . . ?
O3 S1 O2 118.76(7) . . ?
O3 S1 C8 108.55(7) . . ?
O3 S1 C13 108.60(7) . . ?
C13 S1 C8 105.39(7) . . ?
C1 O1 C11 117.61(12) . . ?
O1 C1 C2 116.99(14) . . ?
O1 C1 C6 121.93(14) . . ?
C2 C1 C6 120.89(15) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.81(15) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.38(15) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 Cl1 119.32(13) . . ?
C3 C4 C5 121.63(15) . . ?
C5 C4 Cl1 119.05(13) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.31(14) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 122.00(14) . . ?
C5 C6 C1 117.95(14) . . ?
C5 C6 C7 120.05(13) . . ?
C6 C7 H7 109.7 . . ?
C6 C7 C8 111.89(12) . . ?
C6 C7 C12 112.98(13) . . ?
C8 C7 H7 109.7 . . ?
C12 C7 H7 109.7 . . ?
C12 C7 C8 102.77(12) . . ?
S1 C8 H8 109.4 . . ?
C7 C8 S1 108.07(10) . . ?
C7 C8 H8 109.4 . . ?
C9 C8 S1 113.55(11) . . ?
C9 C8 C7 106.99(12) . . ?
C9 C8 H8 109.4 . . ?
C8 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 C8 103.81(12) . . ?
C10 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
F1 C10 C9 111.17(13) . . ?
F1 C10 C11 104.96(13) . . ?
F1 C10 C12 110.57(14) . . ?
C11 C10 C9 112.37(15) . . ?
C12 C10 C9 103.84(13) . . ?
C12 C10 C11 114.10(14) . . ?
O1 C11 C10 112.63(13) . . ?
O1 C11 H11A 109.1 . . ?
O1 C11 H11B 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C7 C12 H12A 111.2 . . ?
C7 C12 H12B 111.2 . . ?
C10 C12 C7 102.94(13) . . ?
C10 C12 H12A 111.2 . . ?
C10 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
C14 C13 S1 119.06(12) . . ?
C18 C13 S1 120.21(12) . . ?
C18 C13 C14 120.73(14) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.99(15) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.21(15) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C19 120.55(15) . . ?
C17 C16 C15 118.53(15) . . ?
C17 C16 C19 120.92(15) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.28(15) . . ?
C18 C17 H17 119.4 . . ?
C13 C18 H18 120.4 . . ?
C17 C18 C13 119.25(15) . . ?
C17 C18 H18 120.4 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Cl1 C4 C5 C6 -179.73(11) . . . . ?
S1 C8 C9 C10 -131.02(12) . . . . ?
S1 C13 C14 C15 -179.24(12) . . . . ?
S1 C13 C18 C17 179.26(13) . . . . ?
F1 C10 C11 O1 164.18(12) . . . . ?
F1 C10 C12 C7 -164.70(12) . . . . ?
O1 C1 C2 C3 176.97(14) . . . . ?
O1 C1 C6 C5 -177.09(13) . . . . ?
O1 C1 C6 C7 2.4(2) . . . . ?
O2 S1 C8 C7 61.17(11) . . . . ?
O2 S1 C8 C9 179.70(11) . . . . ?
O2 S1 C13 C14 34.24(14) . . . . ?
O2 S1 C13 C18 -145.15(13) . . . . ?
O3 S1 C8 C7 -67.70(12) . . . . ?
O3 S1 C8 C9 50.82(13) . . . . ?
O3 S1 C13 C14 164.54(12) . . . . ?
O3 S1 C13 C18 -14.86(15) . . . . ?
C1 O1 C11 C10 77.97(17) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C1 C6 C7 C8 -52.78(19) . . . . ?
C1 C6 C7 C12 62.63(18) . . . . ?
C2 C1 C6 C5 -2.2(2) . . . . ?
C2 C1 C6 C7 177.25(14) . . . . ?
C2 C3 C4 Cl1 179.32(12) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 -178.46(14) . . . . ?
C5 C6 C7 C8 126.70(14) . . . . ?
C5 C6 C7 C12 -117.89(15) . . . . ?
C6 C1 C2 C3 1.9(2) . . . . ?
C6 C7 C8 S1 -130.96(11) . . . . ?
C6 C7 C8 C9 106.41(14) . . . . ?
C6 C7 C12 C10 -84.13(15) . . . . ?
C7 C8 C9 C10 -11.87(17) . . . . ?
C8 S1 C13 C14 -79.31(14) . . . . ?
C8 S1 C13 C18 101.30(14) . . . . ?
C8 C7 C12 C10 36.62(16) . . . . ?
C8 C9 C10 F1 154.00(13) . . . . ?
C8 C9 C10 C11 -88.69(16) . . . . ?
C8 C9 C10 C12 35.09(17) . . . . ?
C9 C10 C11 O1 43.24(18) . . . . ?
C9 C10 C12 C7 -45.38(17) . . . . ?
C11 O1 C1 C2 123.55(16) . . . . ?
C11 O1 C1 C6 -61.41(19) . . . . ?
C11 C10 C12 C7 77.27(17) . . . . ?
C12 C7 C8 S1 107.54(12) . . . . ?
C12 C7 C8 C9 -15.09(16) . . . . ?
C12 C10 C11 O1 -74.62(18) . . . . ?
C13 S1 C8 C7 176.11(10) . . . . ?
C13 S1 C8 C9 -65.37(12) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C14 C15 C16 C19 178.62(15) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C18 C13 C14 C15 0.2(2) . . . . ?
C19 C16 C17 C18 -178.59(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.720
####################################################################### 
# 
# 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_k10906-myc-d
_database_code_depnum_ccdc_archive 'CCDC 2008547'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2020-06-08 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2020-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H23 Cl O4 S'
_chemical_formula_sum            'C19 H23 Cl O4 S'
_chemical_formula_weight         382.88
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H21 O4 S'
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'
Cl Cl 0.1484 0.1585 '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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.5435(3)
_cell_length_b                   6.0581(2)
_cell_length_c                   20.5872(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.464(2)
_cell_angle_gamma                90.00
_cell_volume                     1810.54(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    23575
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.9690
_cell_measurement_theta_min      2.7930
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35564
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00 100.00   0.50    8.15    --   10.60  82.00  60.00  234
  2  ω    -17.00 100.00   0.50    8.15    --   10.60  82.00-150.00  234
  3  ω    -15.00 100.00   0.50    8.15    --   10.60  77.00  90.00  230
  4  ω    -20.00 100.00   0.50    8.15    --   10.60  57.00 -30.00  240
  5  ω    -79.00  36.00   0.50    8.15    --   10.60 -77.00   0.00  230
  6  ω    -79.00  41.00   0.50    8.15    --   10.60 -57.00 120.00  240
  7  ω    -17.00 100.00   0.50    8.15    --   10.60  82.00 -30.00  234
  8  ω   -100.00  17.00   0.50    8.15    --  -10.90 -82.00-120.00  234
  9  ω   -100.00  17.00   0.50    8.15    --  -10.90 -82.00 120.00  234
 10  ω   -100.00  17.00   0.50    8.15    --  -10.90 -82.00  30.00  234
 11  ω    -54.00  -1.00   0.50    8.15    --  -10.90 -77.00 -60.00  106
 12  ω    -26.00  50.00   0.50    8.15    --  -10.90  57.00-150.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0482982000
_diffrn_orient_matrix_UB_12      0.0146565000
_diffrn_orient_matrix_UB_13      0.0008854000
_diffrn_orient_matrix_UB_21      -0.0025110000
_diffrn_orient_matrix_UB_22      0.0297604000
_diffrn_orient_matrix_UB_23      -0.0333799000
_diffrn_orient_matrix_UB_31      -0.0069789000
_diffrn_orient_matrix_UB_32      -0.1122807000
_diffrn_orient_matrix_UB_33      -0.0087338000
_diffrn_oxdiff_digest_frames     
;
01ced5631da8e27aff867c009b04ba821b000254522
;
_diffrn_oxdiff_digest_hkl        
;
01bd6e6d0efb06e28eacbd398a6573a5c040e7
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_number_gt                2911
_reflns_number_total             3191
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0392P)²+1.3265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0838
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4A), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.03533(3) 0.68893(9) 0.41849(2) 0.03253(14) Uani 1 d . . .
S1 S 0.33549(3) 0.57977(7) 0.570660(19) 0.01680(12) Uani 1 d . . .
O1 O 0.42633(8) 0.6653(2) 0.58880(6) 0.0219(3) Uani 1 d . . .
O2 O 0.32242(8) 0.3438(2) 0.57219(6) 0.0239(3) Uani 1 d . . .
O3 O 0.35735(9) 0.3316(2) 0.43572(6) 0.0268(3) Uani 1 d . . .
H3 H 0.3659 0.2621 0.4709 0.040 Uiso 1 calc . . GR
O4 O 0.47316(8) 0.94135(19) 0.43498(5) 0.0193(3) Uani 1 d . . .
H4 H 0.4986 1.0634 0.4288 0.029 Uiso 1 calc . . GR
C1 C 0.30727(10) 0.6711(3) 0.48842(8) 0.0150(3) Uani 1 d . . .
H1 H 0.3162 0.8345 0.4864 0.018 Uiso 1 calc . . R
C2 C 0.25758(11) 0.7019(3) 0.62206(8) 0.0169(3) Uani 1 d . . .
C3 C 0.17767(11) 0.5898(3) 0.63663(8) 0.0197(4) Uani 1 d . . .
H3A H 0.1652 0.4466 0.6195 0.024 Uiso 1 calc . . R
C4 C 0.11694(11) 0.6900(3) 0.67640(8) 0.0221(4) Uani 1 d . . .
H4A H 0.0623 0.6147 0.6864 0.027 Uiso 1 calc . . R
C5 C 0.13441(12) 0.9003(3) 0.70214(8) 0.0212(4) Uani 1 d . . .
C6 C 0.21578(12) 1.0064(3) 0.68752(8) 0.0210(4) Uani 1 d . . .
H6 H 0.2292 1.1482 0.7054 0.025 Uiso 1 calc . . R
C7 C 0.27721(11) 0.9094(3) 0.64760(8) 0.0189(4) Uani 1 d . . .
H7 H 0.3322 0.9839 0.6378 0.023 Uiso 1 calc . . R
C8 C 0.06713(13) 1.0101(4) 0.74464(9) 0.0304(4) Uani 1 d . . .
H8A H 0.0931 1.1500 0.7611 0.046 Uiso 1 calc . . GR
H8B H 0.0553 0.9131 0.7813 0.046 Uiso 1 calc . . GR
H8C H 0.0093 1.0386 0.7191 0.046 Uiso 1 calc . . GR
C9 C 0.20704(11) 0.6170(3) 0.46498(8) 0.0176(3) Uani 1 d . . .
H9A H 0.2083 0.5174 0.4269 0.021 Uiso 1 calc . . R
H9B H 0.1781 0.5349 0.5000 0.021 Uiso 1 calc . . R
C10 C 0.14603(11) 0.8159(3) 0.44599(8) 0.0206(4) Uani 1 d . . .
C11 C 0.12771(12) 0.9676(3) 0.50263(9) 0.0250(4) Uani 1 d . . .
H11A H 0.0838 1.0825 0.4879 0.038 Uiso 1 calc . . GR
H11B H 0.1856 1.0364 0.5189 0.038 Uiso 1 calc . . GR
H11C H 0.1020 0.8816 0.5375 0.038 Uiso 1 calc . . GR
C12 C 0.17719(13) 0.9465(3) 0.38893(9) 0.0272(4) Uani 1 d . . .
H12A H 0.1850 0.8470 0.3521 0.041 Uiso 1 calc . . GR
H12B H 0.2360 1.0188 0.4011 0.041 Uiso 1 calc . . GR
H12C H 0.1308 1.0586 0.3765 0.041 Uiso 1 calc . . GR
C13 C 0.37954(11) 0.5571(3) 0.44605(8) 0.0181(4) Uani 1 d . . .
H13 H 0.4418 0.5678 0.4692 0.022 Uiso 1 calc . . R
C14 C 0.38176(11) 0.6714(3) 0.38143(8) 0.0171(3) Uani 1 d . . .
C15 C 0.42910(11) 0.8712(3) 0.37833(8) 0.0169(3) Uani 1 d . . .
C16 C 0.42924(11) 0.9898(3) 0.32065(8) 0.0216(4) Uani 1 d . . .
H16 H 0.4617 1.1255 0.3190 0.026 Uiso 1 calc . . R
C17 C 0.38134(12) 0.9077(3) 0.26546(8) 0.0262(4) Uani 1 d . . .
H17 H 0.3801 0.9894 0.2260 0.031 Uiso 1 calc . . R
C18 C 0.33554(12) 0.7087(3) 0.26736(9) 0.0270(4) Uani 1 d . . .
H18 H 0.3035 0.6531 0.2292 0.032 Uiso 1 calc . . R
C19 C 0.33632(11) 0.5897(3) 0.32501(9) 0.0227(4) Uani 1 d . . .
H19 H 0.3056 0.4514 0.3260 0.027 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.8422(17) . ?
S1 O1 1.4468(12) . ?
S1 O2 1.4430(13) . ?
S1 C1 1.8047(16) . ?
S1 C2 1.7596(17) . ?
O3 C13 1.417(2) . ?
O4 C15 1.364(2) . ?
C1 C9 1.543(2) . ?
C1 C13 1.566(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.385(2) . ?
C3 C4 1.381(2) . ?
C4 C5 1.397(3) . ?
C5 C6 1.396(2) . ?
C5 C8 1.506(2) . ?
C6 C7 1.381(2) . ?
C9 C10 1.533(2) . ?
C10 C11 1.521(2) . ?
C10 C12 1.509(3) . ?
C13 C14 1.502(2) . ?
C14 C15 1.396(2) . ?
C14 C19 1.392(2) . ?
C15 C16 1.388(2) . ?
C16 C17 1.389(3) . ?
C17 C18 1.379(3) . ?
C18 C19 1.388(3) . ?

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
O1 S1 C1 106.55(7) . . ?
O1 S1 C2 107.78(8) . . ?
O2 S1 O1 117.94(7) . . ?
O2 S1 C1 107.54(8) . . ?
O2 S1 C2 108.25(8) . . ?
C2 S1 C1 108.48(7) . . ?
C9 C1 S1 112.66(11) . . ?
C9 C1 C13 112.67(13) . . ?
C13 C1 S1 105.38(11) . . ?
C3 C2 S1 119.99(13) . . ?
C7 C2 S1 118.97(13) . . ?
C7 C2 C3 121.04(16) . . ?
C4 C3 C2 118.99(16) . . ?
C3 C4 C5 121.18(16) . . ?
C4 C5 C8 120.89(16) . . ?
C6 C5 C4 118.40(16) . . ?
C6 C5 C8 120.72(17) . . ?
C7 C6 C5 121.30(16) . . ?
C6 C7 C2 119.09(16) . . ?
C10 C9 C1 115.73(14) . . ?
C9 C10 Cl1 103.41(12) . . ?
C11 C10 Cl1 107.31(12) . . ?
C11 C10 C9 113.89(14) . . ?
C12 C10 Cl1 106.13(12) . . ?
C12 C10 C9 114.48(14) . . ?
C12 C10 C11 110.78(16) . . ?
O3 C13 C1 110.74(13) . . ?
O3 C13 C14 109.16(14) . . ?
C14 C13 C1 109.97(13) . . ?
C15 C14 C13 118.50(14) . . ?
C19 C14 C13 122.74(16) . . ?
C19 C14 C15 118.73(16) . . ?
O4 C15 C14 116.00(14) . . ?
O4 C15 C16 123.05(16) . . ?
C16 C15 C14 120.94(15) . . ?
C15 C16 C17 119.21(17) . . ?
C18 C17 C16 120.61(17) . . ?
C17 C18 C19 119.95(16) . . ?
C18 C19 C14 120.51(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.712
_oxdiff_exptl_absorpt_empirical_full_min 0.453
