# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_xcalibur
_database_code_depnum_ccdc_archive 'CCDC 2044374'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H13 Cl O5 S'
_chemical_formula_moiety         'C16 H13 Cl O5 S'
_chemical_formula_weight         352.79
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.5864(3)
_cell_length_b                   6.33745(13)
_cell_length_c                   16.8543(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.954(2)
_cell_angle_gamma                90.0000
_cell_volume                     1490.31(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6686
_cell_measurement_theta_min      5.44
_cell_measurement_theta_max      73.72
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_colour            nONE
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728.00
_exptl_absorpt_coefficient_mu    3.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            13115
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_theta_max         74.40
_diffrn_reflns_theta_min         5.479
_diffrn_reflns_theta_full        74.40
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3015
_reflns_number_gt                2797
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 2.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1334
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2797
_refine_ls_number_parameters     221
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[0.0040Fo² + 1.0000σ(Fo²)]/(4Fo²)'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.463
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl24 Cl 0.67918(3) 0.69601(7) 1.21109(2) 0.02635(13) Uani 1 4 d . . .
S2 S 0.83869(3) 0.33824(7) 0.85659(2) 0.02127(13) Uani 1 4 d . . .
O3 O 0.73987(8) 0.45022(19) 0.85305(7) 0.0219(3) Uani 1 4 d . . .
O4 O 0.90584(9) 0.5076(2) 0.87289(8) 0.0289(3) Uani 1 4 d . . .
O5 O 0.82534(9) 0.2117(2) 0.78392(8) 0.0281(3) Uani 1 4 d . . .
O6 O 0.54190(8) 0.60955(19) 0.82496(7) 0.0213(3) Uani 1 4 d . . .
O7 O 0.51692(9) 0.9286(2) 0.87224(8) 0.0275(3) Uani 1 4 d . . .
C8 C 0.54531(11) 0.7497(3) 0.88626(10) 0.0207(4) Uani 1 4 d . . .
C9 C 0.58939(11) 0.6458(3) 0.96664(10) 0.0190(4) Uani 1 4 d . . .
C10 C 0.65968(12) 0.3112(3) 1.01741(11) 0.0219(4) Uani 1 4 d . . .
C11 C 0.57821(11) 0.4032(3) 0.85947(10) 0.0197(4) Uani 1 4 d . . .
C12 C 0.90897(13) 0.2576(3) 1.02138(12) 0.0268(4) Uani 1 4 d . . .
C13 C 0.65427(11) 0.5976(3) 1.11090(10) 0.0213(4) Uani 1 4 d . . .
C14 C 0.86037(11) 0.1739(3) 0.94409(11) 0.0228(4) Uani 1 4 d . . .
C15 C 0.68138(11) 0.3922(3) 1.09754(10) 0.0227(4) Uani 1 4 d . . .
C16 C 0.60779(11) 0.7299(3) 1.04568(10) 0.0202(4) Uani 1 4 d . . .
C17 C 0.61215(11) 0.4409(3) 0.95169(10) 0.0192(4) Uani 1 4 d . . .
C18 C 0.65298(11) 0.3242(3) 0.82071(11) 0.0211(4) Uani 1 4 d . . .
C19 C 0.82718(12) -0.0332(3) 0.93636(11) 0.0256(4) Uani 1 4 d . . .
C20 C 0.84090(13) -0.1548(3) 1.00756(12) 0.0260(4) Uani 1 4 d . . .
C21 C 0.90646(15) -0.2087(4) 1.16300(13) 0.0337(5) Uani 1 4 d . . .
C22 C 0.88892(12) -0.0746(3) 1.08593(11) 0.0261(4) Uani 1 4 d . . .
C23 C 0.92347(13) 0.1324(3) 1.09112(11) 0.0292(4) Uani 1 4 d . . .
H1 H 0.67664 0.17403 1.00801 0.0269 Uiso 1 4 calc R . .
H2 H 0.93186 0.39535 1.02602 0.0315 Uiso 1 4 calc R . .
H3 H 0.71366 0.30909 1.14247 0.0274 Uiso 1 4 calc R . .
H4 H 0.58977 0.86653 1.05461 0.0249 Uiso 1 4 calc R . .
H5 H 0.52491 0.30256 0.84717 0.0232 Uiso 1 4 calc R . .
H6 H 0.63175 0.33975 0.76086 0.0245 Uiso 1 4 calc R . .
H7 H 0.66883 0.17757 0.83472 0.0252 Uiso 1 4 calc R . .
H8 H 0.79666 -0.08946 0.8844 0.0300 Uiso 1 4 calc R . .
H9 H 0.81714 -0.29188 1.00305 0.0309 Uiso 1 4 calc R . .
H10 H 0.88497 -0.13414 1.20387 0.0415 Uiso 1 4 calc R . .
H11 H 0.87166 -0.33872 1.14942 0.0412 Uiso 1 4 calc R . .
H12 H 0.97368 -0.23836 1.18478 0.0413 Uiso 1 4 calc R . .
H13 H 0.95639 0.18722 1.14276 0.0339 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
Cl24 C13 1.7364(17) yes .
S2 O3 1.5921(13) yes .
S2 O4 1.4246(14) yes .
S2 O5 1.4290(14) yes .
S2 C14 1.7573(18) yes .
O3 C18 1.4623(19) yes .
O6 C8 1.352(2) yes .
O6 C11 1.466(2) yes .
O7 C8 1.207(2) yes .
C8 C9 1.475(2) yes .
C9 C16 1.386(2) yes .
C9 C17 1.381(2) yes .
C10 C15 1.392(2) yes .
C10 C17 1.391(2) yes .
C11 C17 1.506(2) yes .
C11 C18 1.511(3) yes .
C12 C14 1.394(2) yes .
C12 C23 1.382(3) yes .
C13 C15 1.397(3) yes .
C13 C16 1.392(2) yes .
C14 C19 1.392(2) yes .
C19 C20 1.391(3) yes .
C20 C22 1.398(2) yes .
C21 C22 1.510(3) yes .
C22 C23 1.399(3) yes .
C10 H1 0.930 no .
C11 H5 0.980 no .
C12 H2 0.930 no .
C15 H3 0.930 no .
C16 H4 0.930 no .
C18 H6 0.970 no .
C18 H7 0.970 no .
C19 H8 0.930 no .
C20 H9 0.930 no .
C21 H10 0.960 no .
C21 H11 0.960 no .
C21 H12 0.960 no .
C23 H13 0.930 no .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3 S2 O4 103.62(7) yes . .
O3 S2 O5 108.81(7) yes . .
O3 S2 C14 103.60(8) yes . .
O4 S2 O5 120.15(9) yes . .
O4 S2 C14 109.84(7) yes . .
O5 S2 C14 109.44(8) yes . .
S2 O3 C18 116.57(10) yes . .
C8 O6 C11 110.75(12) yes . .
O6 C8 O7 122.25(15) yes . .
O6 C8 C9 108.51(14) yes . .
O7 C8 C9 129.24(16) yes . .
C8 C9 C16 128.41(15) yes . .
C8 C9 C17 108.41(14) yes . .
C16 C9 C17 123.17(15) yes . .
C15 C10 C17 118.28(16) yes . .
O6 C11 C17 103.88(13) yes . .
O6 C11 C18 110.30(14) yes . .
C17 C11 C18 115.93(13) yes . .
C14 C12 C23 119.11(18) yes . .
Cl24 C13 C15 120.17(12) yes . .
Cl24 C13 C16 117.86(13) yes . .
C15 C13 C16 121.97(15) yes . .
S2 C14 C12 118.48(14) yes . .
S2 C14 C19 120.52(13) yes . .
C12 C14 C19 120.98(17) yes . .
C10 C15 C13 120.33(14) yes . .
C9 C16 C13 116.14(15) yes . .
C9 C17 C10 120.04(15) yes . .
C9 C17 C11 108.25(13) yes . .
C10 C17 C11 131.70(16) yes . .
O3 C18 C11 108.32(13) yes . .
C14 C19 C20 118.90(16) yes . .
C19 C20 C22 121.34(17) yes . .
C20 C22 C21 121.37(17) yes . .
C20 C22 C23 118.18(17) yes . .
C21 C22 C23 120.41(16) yes . .
C12 C23 C22 121.46(16) yes . .
C15 C10 H1 120.901 no . .
C17 C10 H1 120.820 no . .
O6 C11 H5 108.915 no . .
C17 C11 H5 108.864 no . .
C18 C11 H5 108.721 no . .
C14 C12 H2 120.549 no . .
C23 C12 H2 120.336 no . .
C10 C15 H3 119.911 no . .
C13 C15 H3 119.762 no . .
C9 C16 H4 121.929 no . .
C13 C16 H4 121.931 no . .
O3 C18 H6 108.137 no . .
O3 C18 H7 108.260 no . .
C11 C18 H6 111.357 no . .
C11 C18 H7 111.294 no . .
H6 C18 H7 109.367 no . .
C14 C19 H8 120.506 no . .
C20 C19 H8 120.595 no . .
C19 C20 H9 119.384 no . .
C22 C20 H9 119.278 no . .
C22 C21 H10 109.360 no . .
C22 C21 H11 109.438 no . .
C22 C21 H12 109.704 no . .
H10 C21 H11 109.441 no . .
H10 C21 H12 109.441 no . .
H11 C21 H12 109.444 no . .
C12 C23 H13 119.399 no . .
C22 C23 H13 119.139 no . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O4 S2 O3 C18 168.05(9) no . . . .
O5 S2 O3 C18 39.11(11) no . . . .
O3 S2 C14 C12 -87.42(12) no . . . .
O3 S2 C14 C19 90.75(13) no . . . .
C14 S2 O3 C18 -77.25(9) no . . . .
O4 S2 C14 C12 22.76(15) no . . . .
O4 S2 C14 C19 -159.08(12) no . . . .
O5 S2 C14 C12 156.66(11) no . . . .
O5 S2 C14 C19 -25.17(15) no . . . .
S2 O3 C18 C11 152.16(9) no . . . .
C8 O6 C11 C17 -4.37(16) no . . . .
C8 O6 C11 C18 -129.24(12) no . . . .
C11 O6 C8 O7 -178.29(14) no . . . .
C11 O6 C8 C9 2.83(16) no . . . .
O6 C8 C9 C16 179.48(14) no . . . .
O6 C8 C9 C17 0.06(18) no . . . .
O7 C8 C9 C16 0.7(3) no . . . .
O7 C8 C9 C17 -178.72(17) no . . . .
C8 C9 C16 C13 -177.26(15) no . . . .
C8 C9 C17 C10 176.49(13) no . . . .
C8 C9 C17 C11 -2.81(18) no . . . .
C16 C9 C17 C10 -3.0(3) no . . . .
C16 C9 C17 C11 177.73(14) no . . . .
C17 C9 C16 C13 2.1(2) no . . . .
C15 C10 C17 C9 1.3(2) no . . . .
C15 C10 C17 C11 -179.62(15) no . . . .
C17 C10 C15 C13 1.1(2) no . . . .
O6 C11 C17 C9 4.31(16) no . . . .
O6 C11 C17 C10 -174.87(15) no . . . .
O6 C11 C18 O3 72.03(14) no . . . .
C17 C11 C18 O3 -45.63(18) no . . . .
C18 C11 C17 C9 125.48(14) no . . . .
C18 C11 C17 C10 -53.7(2) no . . . .
C14 C12 C23 C22 -1.2(3) no . . . .
C23 C12 C14 S2 177.67(15) no . . . .
C23 C12 C14 C19 -0.5(3) no . . . .
Cl24 C13 C15 C10 178.60(11) no . . . .
Cl24 C13 C16 C9 179.84(10) no . . . .
C15 C13 C16 C9 0.4(2) no . . . .
C16 C13 C15 C10 -2.0(3) no . . . .
S2 C14 C19 C20 -176.36(11) no . . . .
C12 C14 C19 C20 1.8(3) no . . . .
C14 C19 C20 C22 -1.4(3) no . . . .
C19 C20 C22 C21 -178.14(16) no . . . .
C19 C20 C22 C23 -0.2(3) no . . . .
C20 C22 C23 C12 1.5(3) no . . . .
C21 C22 C23 C12 179.48(17) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O3 O6 2.9640(17) no . .
O3 C8 3.591(2) no . .
O3 C9 3.531(2) no . .
O3 C10 3.422(2) no . .
O3 C12 3.397(2) no . .
O3 C17 2.836(2) no . .
O3 C19 3.455(2) no . .
O4 C12 2.951(2) no . .
O5 C18 2.850(2) no . .
O5 C19 2.995(2) no . .
O7 C11 3.471(2) no . .
O7 C16 3.103(2) no . .
O7 C17 3.492(2) no . .
C8 C18 3.460(3) no . .
C9 C15 2.743(2) no . .
C9 C18 3.520(3) no . .
C10 C16 2.837(2) no . .
C10 C18 3.289(3) no . .
C12 C20 2.781(3) no . .
C13 C17 2.757(2) no . .
C14 C18 3.273(2) no . .
C14 C22 2.791(3) no . .
C18 C19 3.535(2) no . .
C19 C23 2.782(2) no . .
Cl24 O3 3.2093(12) no . 4_576
Cl24 O5 3.3469(14) no . 4_566
Cl24 O6 3.3842(14) no . 4_576
O3 Cl24 3.2093(12) no . 4_575
O4 C12 3.143(2) no . 3_767
O4 C19 3.413(2) no . 1_565
O4 C20 3.447(3) no . 1_565
O4 C21 3.524(3) no . 3_757
O4 C23 3.300(2) no . 3_767
O5 Cl24 3.3469(14) no . 4_565
O5 C15 3.2961(19) no . 4_565
O6 Cl24 3.3842(14) no . 4_575
O6 O7 3.3814(17) no . 2_646
O6 C13 3.589(2) no . 3_667
O6 C18 3.4480(18) no . 2_656
O7 O6 3.3814(17) no . 2_656
O7 C11 3.163(2) no . 1_565
O7 C16 3.373(2) no . 3_677
O7 C18 3.462(2) no . 1_565
O7 C18 3.5292(19) no . 2_656
C8 C15 3.513(2) no . 3_667
C11 O7 3.163(2) no . 1_545
C11 C13 3.569(2) no . 3_667
C12 O4 3.143(2) no . 3_767
C13 O6 3.589(2) no . 3_667
C13 C11 3.569(2) no . 3_667
C15 O5 3.2961(19) no . 4_566
C15 C8 3.513(2) no . 3_667
C16 O7 3.373(2) no . 3_677
C16 C17 3.398(2) no . 3_667
C17 C16 3.398(2) no . 3_667
C18 O6 3.4480(18) no . 2_646
C18 O7 3.462(2) no . 1_545
C18 O7 3.5292(19) no . 2_646
C19 O4 3.413(2) no . 1_545
C20 O4 3.447(3) no . 1_545
C21 O4 3.524(3) no . 3_757
C23 O4 3.300(2) no . 3_767
Cl24 H3 2.8182 no . .
Cl24 H4 2.7961 no . .
S2 H2 2.8052 no . .
S2 H6 2.9790 no . .
S2 H7 2.6036 no . .
S2 H8 2.8478 no . .
O3 H1 3.4843 no . .
O3 H2 3.4207 no . .
O3 H5 3.2459 no . .
O3 H8 3.5225 no . .
O4 H2 2.5961 no . .
O5 H6 2.8536 no . .
O5 H7 2.6705 no . .
O5 H8 2.6644 no . .
O6 H6 2.5757 no . .
O6 H7 3.2821 no . .
O7 H4 2.9710 no . .
C8 H4 2.8189 no . .
C8 H5 2.9050 no . .
C9 H1 3.2444 no . .
C9 H5 2.9267 no . .
C10 H5 2.9683 no . .
C10 H7 3.2335 no . .
C11 H1 2.8883 no . .
C12 H1 3.3719 no . .
C12 H8 3.2626 no . .
C13 H1 3.2631 no . .
C14 H1 3.1665 no . .
C14 H7 2.8637 no . .
C14 H9 3.2346 no . .
C14 H13 3.2320 no . .
C15 H4 3.2832 no . .
C16 H3 3.2692 no . .
C17 H3 3.2331 no . .
C17 H4 3.2742 no . .
C17 H6 3.3725 no . .
C17 H7 2.8821 no . .
C18 H1 3.2179 no . .
C18 H8 3.3324 no . .
C19 H1 3.0905 no . .
C19 H2 3.2627 no . .
C19 H7 2.7832 no . .
C20 H1 3.1772 no . .
C20 H10 3.1839 no . .
C20 H11 2.5788 no . .
C20 H12 3.0950 no . .
C20 H13 3.2389 no . .
C21 H9 2.6823 no . .
C21 H13 2.6620 no . .
C22 H1 3.3799 no . .
C22 H2 3.2635 no . .
C22 H8 3.2698 no . .
C23 H1 3.4717 no . .
C23 H3 3.5935 no . .
C23 H9 3.2399 no . .
C23 H10 2.7208 no . .
C23 H11 3.2993 no . .
C23 H12 2.8064 no . .
H1 H3 2.3337 no . .
H1 H5 3.0678 no . .
H1 H7 2.8896 no . .
H1 H8 3.5101 no . .
H2 H13 2.3084 no . .
H5 H6 2.4336 no . .
H5 H7 2.3098 no . .
H7 H8 2.4761 no . .
H8 H9 2.3207 no . .
H9 H10 3.3884 no . .
H9 H11 2.3796 no . .
H9 H12 3.2606 no . .
H10 H13 2.6305 no . .
H11 H13 3.5680 no . .
H12 H13 2.7812 no . .
Cl24 H5 2.8498 no . 3_667
Cl24 H6 3.1901 no . 4_576
Cl24 H7 3.1864 no . 4_566
Cl24 H8 3.0009 no . 4_566
Cl24 H10 3.2244 no . 1_565
Cl24 H11 3.2731 no . 1_565
S2 H9 3.4842 no . 1_565
S2 H10 3.4075 no . 4_565
S2 H12 3.0806 no . 3_757
O3 H8 3.0365 no . 1_565
O3 H9 2.9447 no . 1_565
O4 H2 2.5561 no . 3_767
O4 H8 3.0457 no . 1_565
O4 H9 3.1237 no . 1_565
O4 H10 2.8889 no . 4_565
O4 H11 3.5399 no . 3_757
O4 H12 2.8178 no . 3_757
O4 H13 2.8563 no . 3_767
O5 H3 2.4677 no . 4_565
O5 H10 3.2293 no . 4_565
O5 H11 3.4750 no . 4_555
O5 H12 2.8283 no . 3_757
O5 H13 3.5181 no . 4_565
O6 H5 3.0354 no . 2_656
O6 H6 2.9154 no . 2_656
O6 H7 3.4717 no . 2_656
O7 H1 3.1580 no . 1_565
O7 H4 2.5973 no . 3_677
O7 H5 2.4158 no . 1_565
O7 H6 2.6861 no . 2_656
O7 H7 2.9352 no . 1_565
C8 H1 3.5803 no . 1_565
C8 H4 3.4547 no . 3_677
C8 H5 3.5614 no . 1_565
C8 H6 3.0675 no . 2_656
C8 H7 3.5022 no . 1_565
C9 H1 3.5772 no . 1_565
C9 H9 3.2218 no . 1_565
C10 H4 3.1221 no . 1_545
C10 H9 3.4620 no . 1_565
C12 H2 3.4567 no . 3_767
C12 H9 3.1308 no . 1_565
C12 H11 3.4906 no . 1_565
C13 H5 2.9679 no . 3_667
C13 H9 3.4580 no . 1_565
C13 H11 3.0723 no . 1_565
C15 H4 3.5841 no . 1_545
C15 H6 3.3801 no . 4_566
C15 H9 3.5077 no . 1_565
C15 H11 3.1559 no . 1_565
C16 H1 3.1156 no . 1_565
C16 H5 3.0148 no . 3_667
C16 H9 3.3376 no . 1_565
C17 H4 3.5072 no . 3_667
C17 H9 3.3238 no . 1_565
C18 H3 3.4745 no . 4_565
C20 H2 3.1214 no . 1_545
C21 H2 3.5020 no . 1_545
C21 H13 3.3668 no . 2_747
H1 O7 3.1580 no . 1_545
H1 C8 3.5803 no . 1_545
H1 C9 3.5772 no . 1_545
H1 C16 3.1156 no . 1_545
H1 H4 2.5692 no . 1_545
H2 O4 2.5561 no . 3_767
H2 C12 3.4567 no . 3_767
H2 C20 3.1214 no . 1_565
H2 C21 3.5020 no . 1_565
H2 H2 2.7381 no . 3_767
H2 H9 2.5497 no . 1_565
H2 H11 3.0004 no . 1_565
H2 H12 3.4596 no . 1_565
H3 O5 2.4677 no . 4_566
H3 C18 3.4745 no . 4_566
H3 H4 3.4299 no . 1_545
H3 H6 2.7729 no . 4_566
H3 H7 3.4885 no . 4_566
H3 H11 3.1858 no . 1_565
H4 O7 2.5973 no . 3_677
H4 C8 3.4547 no . 3_677
H4 C10 3.1221 no . 1_565
H4 C15 3.5841 no . 1_565
H4 C17 3.5072 no . 3_667
H4 H1 2.5692 no . 1_565
H4 H3 3.4299 no . 1_565
H4 H4 3.2089 no . 3_677
H4 H5 2.8813 no . 3_667
H5 Cl24 2.8498 no . 3_667
H5 O6 3.0354 no . 2_646
H5 O7 2.4158 no . 1_545
H5 C8 3.5614 no . 1_545
H5 C13 2.9679 no . 3_667
H5 C16 3.0148 no . 3_667
H5 H4 2.8813 no . 3_667
H6 Cl24 3.1901 no . 4_575
H6 O6 2.9154 no . 2_646
H6 O7 2.6861 no . 2_646
H6 C8 3.0675 no . 2_646
H6 C15 3.3801 no . 4_565
H6 H3 2.7729 no . 4_565
H7 Cl24 3.1864 no . 4_565
H7 O6 3.4717 no . 2_646
H7 O7 2.9352 no . 1_545
H7 C8 3.5022 no . 1_545
H7 H3 3.4885 no . 4_565
H8 Cl24 3.0009 no . 4_565
H8 O3 3.0365 no . 1_545
H8 O4 3.0457 no . 1_545
H9 S2 3.4842 no . 1_545
H9 O3 2.9447 no . 1_545
H9 O4 3.1237 no . 1_545
H9 C9 3.2218 no . 1_545
H9 C10 3.4620 no . 1_545
H9 C12 3.1308 no . 1_545
H9 C13 3.4580 no . 1_545
H9 C15 3.5077 no . 1_545
H9 C16 3.3376 no . 1_545
H9 C17 3.3238 no . 1_545
H9 H2 2.5497 no . 1_545
H10 Cl24 3.2244 no . 1_545
H10 S2 3.4075 no . 4_566
H10 O4 2.8889 no . 4_566
H10 O5 3.2293 no . 4_566
H10 H12 3.4362 no . 2_757
H10 H13 3.1352 no . 2_747
H11 Cl24 3.2731 no . 1_545
H11 O4 3.5399 no . 3_757
H11 O5 3.4750 no . 4_556
H11 C12 3.4906 no . 1_545
H11 C13 3.0723 no . 1_545
H11 C15 3.1559 no . 1_545
H11 H2 3.0004 no . 1_545
H11 H3 3.1858 no . 1_545
H11 H13 3.2630 no . 1_545
H12 S2 3.0806 no . 3_757
H12 O4 2.8178 no . 3_757
H12 O5 2.8283 no . 3_757
H12 H2 3.4596 no . 1_545
H12 H10 3.4362 no . 2_747
H12 H13 2.8253 no . 2_747
H13 O4 2.8563 no . 3_767
H13 O5 3.5181 no . 4_566
H13 C21 3.3668 no . 2_757
H13 H10 3.1352 no . 2_757
H13 H11 3.2630 no . 1_565
H13 H12 2.8253 no . 2_757

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_609
_database_code_depnum_ccdc_archive 'CCDC 2044376'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2019-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 Cl O5 S'
_chemical_formula_sum            'C16 H13 Cl O5 S'
_chemical_formula_weight         352.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H13 Cl1 O2 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   8.0999(3)
_cell_length_b                   12.5418(5)
_cell_length_c                   15.0076(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.647(4)
_cell_angle_gamma                90
_cell_volume                     1517.18(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2410
_cell_measurement_temperature    123
_cell_measurement_theta_max      67.8360
_cell_measurement_theta_min      4.5820
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.807
_exptl_absorpt_coefficient_mu    3.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (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    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7515
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.924
_diffrn_reflns_theta_min         4.604
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  25.00   0.50    0.05    --    0.00  81.00 -47.00   96
  2  ω     43.00  68.00   0.50    0.05    --    0.00  81.00 -47.00   50
  3  ω     72.00 130.00   0.50    0.05    --   53.00 125.00-120.00  116
  4  ω     93.00 152.00   0.50    0.05    --   96.50 111.00-120.00  118
  5  ω     41.00  88.00   0.50    0.05    --    0.00 178.00-150.00   94
  6  ω    -42.00 -17.00   0.50    0.05    -- -106.00 111.00-180.00   50
  7  ω    -61.00 -33.00   0.50    0.05    --  -53.00  81.00 -47.00   56
  8  ω    -95.00 -54.00   0.50    0.05    -- -106.00  81.00 -47.00   82
  9  ω   -104.00 -41.00   0.50    0.05    -- -106.00 111.00 -60.00  126
 10  ω   -111.00 -68.00   0.50    0.05    -- -106.00 111.00-180.00   86
 11  ω   -122.00  -7.00   0.50    0.05    --  -53.00 -81.00-169.00  230
 12  ω    -47.00 -22.00   0.50    0.05    --    0.00 -81.00-169.00   50
 13  ω      6.00  31.00   0.50    0.05    --   53.00 -81.00-169.00   50
 14  ω     49.00  74.00   0.50    0.05    --   96.50 -81.00-169.00   50
 15  ω   -101.00 -75.00   0.50    0.05    --  -53.00-125.00 120.00   52
 16  ω   -119.00 -84.00   0.50    0.05    --  -53.00 -99.00 150.00   70
 17  ω   -138.00 -92.00   0.50    0.05    -- -106.00 -91.00  90.00   92
 18  ω   -111.00 -65.00   0.50    0.05    -- -106.00 -63.00 150.00   92
 19  ω   -142.00 -94.00   0.50    0.05    --  -53.00 -99.00 120.00   96
 20  ω   -155.00-116.00   0.50    0.05    -- -106.00 -63.00 150.00   78
 21  ω   -176.00-144.00   0.50    0.05    -- -106.00 -91.00  90.00   64
 22  ω   -177.00 -76.00   0.50    0.05    -- -106.00 -91.00 120.00  202
 23  ω   -158.00-126.00   0.50    0.05    -- -106.00 -91.00 -60.00   64
 24  ω   -110.00 -83.00   0.50    0.05    -- -106.00 -91.00 -60.00   54
 25  ω    -90.00 -62.00   0.50    0.05    -- -106.00 -81.00-169.00   56
 26  ω   -148.00 -84.00   0.50    0.05    --  -53.00 -99.00 -90.00  128
 27  ω   -148.00-120.00   0.50    0.05    --  -53.00 -99.00-150.00   56
 28  ω   -177.00-100.00   0.50    0.05    -- -106.00 -81.00-169.00  154
 29  ω   -172.00 -83.00   0.50    0.05    -- -106.00-111.00-120.00  178
 30  ω    -86.00 -52.00   0.50    0.05    -- -106.00  77.00 120.00   68
 31  ω    -65.00 -38.00   0.50    0.05    -- -106.00 111.00  90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1103902000
_diffrn_orient_matrix_UB_12      -0.0338175000
_diffrn_orient_matrix_UB_13      -0.0730848000
_diffrn_orient_matrix_UB_21      0.0531433000
_diffrn_orient_matrix_UB_22      -0.1006312000
_diffrn_orient_matrix_UB_23      0.0543282000
_diffrn_orient_matrix_UB_31      -0.1466111000
_diffrn_orient_matrix_UB_32      -0.0620480000
_diffrn_orient_matrix_UB_33      -0.0482371000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2416
_reflns_number_total             2730
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (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    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      0.940
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1243
_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:
 C013(H013)
2.b Secondary CH2 refined with riding coordinates:
 C012(H01A,H01B)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C016(H016), C018(H018), C020(H020), C021(H021),
 C023(H023)
2.d Idealised Me refined as rotating group:
 C022(H02A,H02B,H02C)
;
_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
Cl01 Cl 0.47211(5) 0.05022(4) 0.23708(3) 0.02342(18) Uani 1 1 d . . . . .
S002 S 0.67563(6) -0.35704(4) -0.06024(3) 0.02180(19) Uani 1 1 d . . . . .
O2 O 0.79371(16) -0.24738(10) 0.19970(9) 0.0189(3) Uani 1 1 d . . . . .
O3 O 0.61331(16) -0.33041(11) 0.03418(9) 0.0206(3) Uani 1 1 d . . . . .
O4 O 0.7079(2) -0.46930(12) -0.06414(11) 0.0307(4) Uani 1 1 d . . . . .
O1 O 0.81877(16) -0.07039(11) 0.21767(10) 0.0239(3) Uani 1 1 d . . . . .
O5 O 0.55400(18) -0.30844(14) -0.12259(10) 0.0312(4) Uani 1 1 d . . . . .
C008 C 0.2597(2) -0.11518(17) 0.20894(13) 0.0193(4) Uani 1 1 d . . . . .
H008 H 0.173837 -0.064490 0.213699 0.023 Uiso 1 1 calc R . . . .
C009 C 0.3430(2) -0.29844(16) 0.18690(13) 0.0194(4) Uani 1 1 d . . . . .
H009 H 0.315545 -0.371259 0.176192 0.023 Uiso 1 1 calc R . . . .
C010 C 0.5067(2) -0.26476(15) 0.19688(12) 0.0154(4) Uani 1 1 d . . . . .
C011 C 0.7306(2) -0.14785(15) 0.21135(13) 0.0169(4) Uani 1 1 d . . . . .
C012 C 0.6742(2) -0.39444(15) 0.11122(13) 0.0192(4) Uani 1 1 d . . . . .
H01A H 0.790417 -0.416301 0.106264 0.023 Uiso 1 1 calc R . . . .
H01B H 0.605755 -0.459481 0.114268 0.023 Uiso 1 1 calc R . . . .
C013 C 0.6643(2) -0.32779(15) 0.19389(13) 0.0163(4) Uani 1 1 d . . . . .
H013 H 0.680145 -0.374831 0.247861 0.020 Uiso 1 1 calc R . . . .
C014 C 0.5484(2) -0.15880(15) 0.21056(13) 0.0152(4) Uani 1 1 d . . . . .
C015 C 0.4250(2) -0.08267(16) 0.21782(13) 0.0164(4) Uani 1 1 d . . . . .
C016 C 1.1599(3) -0.28150(19) -0.03667(15) 0.0276(5) Uani 1 1 d . . . . .
H016 H 1.262979 -0.317510 -0.025193 0.033 Uiso 1 1 calc R . . . .
C017 C 0.8629(2) -0.28668(17) -0.05844(13) 0.0204(4) Uani 1 1 d . . . . .
C018 C 1.0137(3) -0.33997(18) -0.04190(15) 0.0244(5) Uani 1 1 d . . . . .
H018 H 1.016528 -0.415166 -0.034310 0.029 Uiso 1 1 calc R . . . .
C019 C 1.1589(3) -0.17115(19) -0.04789(13) 0.0249(5) Uani 1 1 d . . . . .
C020 C 1.0062(3) -0.12052(18) -0.06733(15) 0.0287(5) Uani 1 1 d . . . . .
H020 H 1.003195 -0.045723 -0.077367 0.034 Uiso 1 1 calc R . . . .
C021 C 0.8586(3) -0.17746(18) -0.07229(15) 0.0277(5) Uani 1 1 d . . . . .
H021 H 0.755529 -0.141820 -0.085069 0.033 Uiso 1 1 calc R . . . .
C022 C 1.3170(3) -0.1083(2) -0.03748(16) 0.0346(6) Uani 1 1 d . . . . .
H02A H 1.358863 -0.105048 0.025993 0.052 Uiso 1 1 calc GR . . . .
H02B H 1.295856 -0.035819 -0.060290 0.052 Uiso 1 1 calc GR . . . .
H02C H 1.399611 -0.142791 -0.071327 0.052 Uiso 1 1 calc GR . . . .
C023 C 0.2205(2) -0.22199(16) 0.19310(14) 0.0205(4) Uani 1 1 d . . . . .
H023 H 0.107286 -0.243132 0.186371 0.025 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C015 1.728(2) . ?
S002 O3 1.5859(14) . ?
S002 O4 1.4343(16) . ?
S002 O5 1.4270(16) . ?
S002 C017 1.753(2) . ?
O2 C011 1.367(2) . ?
O2 C013 1.451(2) . ?
O3 C012 1.454(2) . ?
O1 C011 1.204(2) . ?
C008 C015 1.393(3) . ?
C008 C023 1.392(3) . ?
C009 C010 1.386(3) . ?
C009 C023 1.390(3) . ?
C010 C013 1.506(2) . ?
C010 C014 1.381(3) . ?
C011 C014 1.481(2) . ?
C012 C013 1.505(3) . ?
C014 C015 1.394(3) . ?
C016 C018 1.388(3) . ?
C016 C019 1.394(3) . ?
C017 C018 1.393(3) . ?
C017 C021 1.385(3) . ?
C019 C020 1.395(3) . ?
C019 C022 1.499(3) . ?
C020 C021 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
O3 S002 C017 103.37(9) . . ?
O4 S002 O3 108.57(9) . . ?
O4 S002 C017 109.49(10) . . ?
O5 S002 O3 103.65(8) . . ?
O5 S002 O4 120.63(10) . . ?
O5 S002 C017 109.61(10) . . ?
C011 O2 C013 111.44(14) . . ?
C012 O3 S002 118.78(12) . . ?
C023 C008 C015 119.94(18) . . ?
C010 C009 C023 117.70(18) . . ?
C009 C010 C013 129.91(18) . . ?
C014 C010 C009 121.77(18) . . ?
C014 C010 C013 108.31(16) . . ?
O2 C011 C014 107.41(15) . . ?
O1 C011 O2 121.38(17) . . ?
O1 C011 C014 131.17(18) . . ?
O3 C012 C013 107.91(15) . . ?
O2 C013 C010 104.04(14) . . ?
O2 C013 C012 109.80(16) . . ?
C012 C013 C010 115.49(15) . . ?
C010 C014 C011 108.60(17) . . ?
C010 C014 C015 120.26(17) . . ?
C015 C014 C011 131.10(17) . . ?
C008 C015 Cl01 119.52(15) . . ?
C008 C015 C014 118.79(18) . . ?
C014 C015 Cl01 121.68(15) . . ?
C018 C016 C019 121.5(2) . . ?
C018 C017 S002 120.24(17) . . ?
C021 C017 S002 119.12(16) . . ?
C021 C017 C018 120.63(19) . . ?
C016 C018 C017 119.0(2) . . ?
C016 C019 C020 118.1(2) . . ?
C016 C019 C022 121.0(2) . . ?
C020 C019 C022 120.9(2) . . ?
C021 C020 C019 121.2(2) . . ?
C017 C021 C020 119.5(2) . . ?
C009 C023 C008 121.52(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 1.329
_oxdiff_exptl_absorpt_empirical_full_min 0.820
####################################################################### 
# 
# 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_1057
_database_code_depnum_ccdc_archive 'CCDC 2044377'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2020-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 Cl O5 S'
_chemical_formula_sum            'C16 H13 Cl O5 S'
_chemical_formula_weight         352.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H13 Cl1 O5 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   6.63800(10)
_cell_length_b                   16.3754(2)
_cell_length_c                   13.9858(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.9710(10)
_cell_angle_gamma                90
_cell_volume                     1519.36(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8776
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.0960
_cell_measurement_theta_min      4.1190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.732
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14872
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.418
_diffrn_reflns_theta_min         4.158
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00   1.00   0.50    0.05    --  -42.80  57.00   0.00  130
  2  ω    -53.00 -28.00   0.50    0.05    --  -42.80 100.00  31.00   50
  3  ω    -56.00 -31.00   0.50    0.21    -- -106.00  37.00  60.00   50
  4  ω    -57.00 -32.00   0.50    0.21    -- -106.00  77.00   0.00   50
  5  ω    -80.00 -41.00   0.50    0.21    -- -106.00 100.00  31.00   78
  6  ω    -85.00 -59.00   0.50    0.21    -- -106.00  47.00  64.81   52
  7  ω    -81.00 -47.00   0.50    0.21    -- -106.00  77.00  30.00   68
  8  ω    -77.00 -29.00   0.50    0.21    -- -106.00   0.00 -30.00   96
  9  ω    -70.00 -36.00   0.50    0.21    -- -106.00  37.00 -90.00   68
 10  ω    -77.00 -44.00   0.50    0.21    -- -106.00  57.00-120.00   66
 11  ω    -69.00 -43.00   0.50    0.21    -- -106.00 125.00-120.00   52
 12  ω   -108.00 -32.00   0.50    0.21    -- -106.00 125.00 -60.00  152
 13  ω   -117.00 -85.00   0.50    0.21    -- -106.00 125.00-120.00   64
 14  ω   -120.00 -88.00   0.50    0.21    -- -106.00  77.00-150.00   64
 15  ω   -120.00 -87.00   0.50    0.21    -- -106.00  37.00 -90.00   66
 16  ω   -124.00 -97.00   0.50    0.21    -- -106.00  57.00-120.00   54
 17  ω   -135.00 -70.00   0.50    0.21    -- -106.00  77.00   0.00  130
 18  ω   -127.00 -87.00   0.50    0.21    -- -106.00  47.00  64.81   80
 19  ω   -107.00 -55.00   0.50    0.21    -- -106.00  77.00 120.00  104
 20  ω   -138.00 -84.00   0.50    0.21    -- -106.00 -37.00  90.00  108
 21  ω   -122.00 -92.00   0.50    0.21    -- -106.00 -57.00  30.00   60
 22  ω   -107.00 -82.00   0.50    0.21    -- -106.00-100.00 -72.00   50
 23  ω   -124.00 -97.00   0.50    0.21    -- -106.00 -99.00 -60.00   54
 24  ω   -123.00 -97.00   0.50    0.21    -- -106.00 -37.00 -90.00   52
 25  ω   -135.00 -78.00   0.50    0.21    -- -106.00 -77.00-150.00  114
 26  ω   -110.00 -85.00   0.50    0.21    -- -106.00 -99.00-180.00   50
 27  ω   -115.00 -71.00   0.50    0.05    --  -42.80-125.00 -90.00   88
 28  ω   -115.00 -86.00   0.50    0.05    --  -42.80-125.00-180.00   58
 29  ω   -153.00-127.00   0.50    0.21    -- -106.00 -77.00 -60.00   52
 30  ω   -157.00-116.00   0.50    0.21    -- -106.00 -57.00-120.00   82
 31  ω   -169.00-144.00   0.50    0.21    -- -106.00   0.00 -30.00   50
 32  ω   -175.00-150.00   0.50    0.21    -- -106.00 -57.00  30.00   50
 33  ω   -142.00 -92.00   0.50    0.21    -- -106.00 -99.00   0.00  100
 34  ω   -171.00-136.00   0.50    0.21    -- -106.00-100.00 -72.00   70
 35  ω   -164.00-138.00   0.50    0.21    -- -106.00 -99.00-180.00   52
 36  ω   -177.00-143.00   0.50    0.21    -- -106.00 -77.00-120.00   68
 37  ω   -177.00-151.00   0.50    0.21    -- -106.00 -37.00 -90.00   52
 38  ω   -119.00 -94.00   0.50    0.21    -- -106.00  37.00  60.00   50
 39  ω   -127.00-102.00   0.50    0.21    -- -106.00  77.00  30.00   50
 40  ω     29.00  54.00   0.50    0.05    --   42.80-100.00 -72.00   50
 41  ω     74.00  99.00   0.50    0.21    --   76.50-100.00 -72.00   50
 42  ω     91.00 136.00   0.50    0.21    --   76.50 100.00  31.00   90
 43  ω     71.00  96.00   0.50    0.05    --   42.80 125.00-120.00   50
 44  ω     72.00 105.00   0.50    0.05    --   42.80 125.00 -90.00   66
 45  ω     71.00 112.00   0.50    0.05    --   42.80 125.00 150.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0453439000
_diffrn_orient_matrix_UB_12      0.0837676000
_diffrn_orient_matrix_UB_13      -0.0461758000
_diffrn_orient_matrix_UB_21      0.0762045000
_diffrn_orient_matrix_UB_22      -0.0316608000
_diffrn_orient_matrix_UB_23      -0.0959960000
_diffrn_orient_matrix_UB_31      -0.2144255000
_diffrn_orient_matrix_UB_32      -0.0288560000
_diffrn_orient_matrix_UB_33      -0.0286117000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2886
_reflns_number_total             3067
_reflns_odcompleteness_completeness 98.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (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         0.558
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.063
_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)+(0.0771P)²+0.6545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1244
_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:
 C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00B,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00G(H00G), C00I(H00I), C00K(H00K),
 C00L(H00L)
2.d Idealised Me refined as rotating group:
 C00N(H00H,H00J,H00M)
;
_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 0.64627(7) 0.34417(2) 0.39211(3) 0.02131(16) Uani 1 1 d . . . . .
Cl02 Cl 0.72679(8) 0.65419(3) 0.12037(3) 0.03162(17) Uani 1 1 d . . . . .
O003 O 0.48511(19) 0.35521(7) 0.30680(9) 0.0203(3) Uani 1 1 d . . . . .
O004 O 0.22913(19) 0.29812(8) 0.14824(10) 0.0272(3) Uani 1 1 d . . . . .
O005 O 0.5278(2) 0.34834(9) 0.47506(10) 0.0325(4) Uani 1 1 d . . . . .
O006 O 0.7667(2) 0.27351(8) 0.37410(11) 0.0314(3) Uani 1 1 d . . . . .
O007 O -0.0232(2) 0.37795(9) 0.10388(10) 0.0305(3) Uani 1 1 d . . . . .
C008 C 0.7978(3) 0.43143(11) 0.38335(11) 0.0203(4) Uani 1 1 d . . . . .
C009 C 0.4954(3) 0.43351(11) 0.16186(12) 0.0207(4) Uani 1 1 d . . . . .
C00A C 0.6272(3) 0.49935(11) 0.16197(12) 0.0219(4) Uani 1 1 d . . . . .
H00A H 0.760580 0.494313 0.188138 0.026 Uiso 1 1 calc R . . . .
C00B C 0.2982(3) 0.44170(11) 0.12246(12) 0.0204(4) Uani 1 1 d . . . . .
C00C C 0.7151(3) 0.50742(11) 0.40278(12) 0.0228(4) Uani 1 1 d . . . . .
H00C H 0.581761 0.511614 0.424869 0.027 Uiso 1 1 calc R . . . .
C00D C 0.9950(3) 0.42365(11) 0.35344(12) 0.0230(4) Uani 1 1 d . . . . .
H00D H 1.051700 0.371389 0.342259 0.028 Uiso 1 1 calc R . . . .
C00E C 0.5532(3) 0.35335(10) 0.20740(12) 0.0209(4) Uani 1 1 d . . . . .
H00E H 0.702327 0.344947 0.206331 0.025 Uiso 1 1 calc R . . . .
C00F C 0.1560(3) 0.37159(11) 0.12259(12) 0.0217(4) Uani 1 1 d . . . . .
C00G C 0.8300(3) 0.57707(11) 0.38948(13) 0.0240(4) Uani 1 1 d . . . . .
H00G H 0.774975 0.629154 0.403227 0.029 Uiso 1 1 calc R . . . .
C00H C 1.0263(3) 0.57151(12) 0.35599(12) 0.0235(4) Uani 1 1 d . . . . .
C00I C 0.2339(3) 0.51679(12) 0.08626(12) 0.0253(4) Uani 1 1 d . . . . .
H00I H 0.099722 0.522711 0.061367 0.030 Uiso 1 1 calc R . . . .
C00J C 0.5595(3) 0.57262(11) 0.12299(12) 0.0230(4) Uani 1 1 d . . . . .
C00K C 1.1066(3) 0.49435(12) 0.34039(13) 0.0246(4) Uani 1 1 d . . . . .
H00K H 1.241430 0.489871 0.320274 0.029 Uiso 1 1 calc R . . . .
C00L C 0.3638(3) 0.58297(11) 0.08620(13) 0.0260(4) Uani 1 1 d . . . . .
H00L H 0.320172 0.634319 0.061583 0.031 Uiso 1 1 calc R . . . .
C00M C 0.4436(3) 0.28413(11) 0.15739(14) 0.0252(4) Uani 1 1 d . . . . .
H00B H 0.498005 0.276912 0.092907 0.030 Uiso 1 1 calc R . . . .
H00F H 0.468706 0.233045 0.193734 0.030 Uiso 1 1 calc R . . . .
C00N C 1.1456(3) 0.64701(13) 0.33627(16) 0.0327(5) Uani 1 1 d . . . . .
H00H H 1.115937 0.665248 0.270553 0.049 Uiso 1 1 calc GR . . . .
H00J H 1.289845 0.634982 0.344331 0.049 Uiso 1 1 calc GR . . . .
H00M H 1.109155 0.690164 0.381040 0.049 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 O003 1.5852(13) . ?
S1 O005 1.4252(15) . ?
S1 O006 1.4335(14) . ?
S1 C008 1.7540(18) . ?
Cl02 C00J 1.7380(19) . ?
O003 C00E 1.477(2) . ?
O004 C00F 1.342(2) . ?
O004 C00M 1.443(2) . ?
O007 C00F 1.214(2) . ?
C008 C00C 1.391(2) . ?
C008 C00D 1.394(3) . ?
C009 C00A 1.388(3) . ?
C009 C00B 1.409(3) . ?
C009 C00E 1.503(2) . ?
C00A C00J 1.386(3) . ?
C00B C00F 1.487(3) . ?
C00B C00I 1.391(3) . ?
C00C C00G 1.388(3) . ?
C00D C00K 1.390(3) . ?
C00E C00M 1.506(3) . ?
C00G C00H 1.403(3) . ?
C00H C00K 1.392(3) . ?
C00H C00N 1.499(3) . ?
C00I C00L 1.385(3) . ?
C00J C00L 1.391(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
O003 S1 C008 103.19(7) . . ?
O005 S1 O003 103.32(8) . . ?
O005 S1 O006 120.54(9) . . ?
O005 S1 C008 110.58(8) . . ?
O006 S1 O003 109.01(8) . . ?
O006 S1 C008 108.71(9) . . ?
C00E O003 S1 119.06(11) . . ?
C00F O004 C00M 120.86(14) . . ?
C00C C008 S1 118.97(14) . . ?
C00C C008 C00D 121.42(16) . . ?
C00D C008 S1 119.56(14) . . ?
C00A C009 C00B 120.22(16) . . ?
C00A C009 C00E 121.75(16) . . ?
C00B C009 C00E 117.96(16) . . ?
C00J C00A C009 118.44(17) . . ?
C009 C00B C00F 120.51(16) . . ?
C00I C00B C009 119.73(17) . . ?
C00I C00B C00F 119.72(16) . . ?
C00G C00C C008 119.13(16) . . ?
C00K C00D C008 118.28(16) . . ?
O003 C00E C009 107.39(13) . . ?
O003 C00E C00M 107.11(14) . . ?
C009 C00E C00M 110.39(15) . . ?
O004 C00F C00B 117.95(15) . . ?
O007 C00F O004 118.54(17) . . ?
O007 C00F C00B 123.47(17) . . ?
C00C C00G C00H 120.82(16) . . ?
C00G C00H C00N 120.72(17) . . ?
C00K C00H C00G 118.47(17) . . ?
C00K C00H C00N 120.81(17) . . ?
C00L C00I C00B 120.56(17) . . ?
C00A C00J Cl02 118.36(15) . . ?
C00A C00J C00L 122.45(17) . . ?
C00L C00J Cl02 119.19(14) . . ?
C00D C00K C00H 121.79(16) . . ?
C00I C00L C00J 118.55(16) . . ?
O004 C00M C00E 112.39(15) . . ?

_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 3.501
_oxdiff_exptl_absorpt_empirical_full_min 0.358
####################################################################### 
# 
# 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_485
_database_code_depnum_ccdc_archive 'CCDC 2044375'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2020-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 Cl O5 S'
_chemical_formula_sum            'C16 H13 Cl O5 S'
_chemical_formula_weight         352.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H13 Cl1 O5 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'
Cl Cl 0.1484 0.1585 '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                   13.4210(7)
_cell_length_b                   7.0455(3)
_cell_length_c                   16.8841(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.499(5)
_cell_angle_gamma                90
_cell_volume                     1514.03(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6916
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.3830
_cell_measurement_theta_min      2.5270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.818
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.761
_diffrn_reflns_theta_min         2.339
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.818
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  25.00   0.50   10.03    --    5.34-112.00  -5.00   50
  2  ω    -23.00  18.00   0.50   10.03    --   -5.03 -99.00 -90.00   82
  3  ω    -21.00  27.00   0.50   10.03    --   -5.03 -99.00-150.00   96
  4  ω    -25.00  28.00   0.50   10.03    --    5.34 -99.00 -60.00  106
  5  ω    -15.00  26.00   0.50   10.03    --   -5.03 -99.00  90.00   82
  6  ω    -12.00  21.00   0.50   10.03    --   -5.03 -99.00 150.00   66
  7  ω    -18.00   7.00   0.50   10.03    --   -5.03 -99.00 120.00   50
  8  ω    -22.00   3.00   0.50   10.03    --    5.34 -99.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0369875000
_diffrn_orient_matrix_UB_12      -0.0751155000
_diffrn_orient_matrix_UB_13      -0.0098876000
_diffrn_orient_matrix_UB_21      0.0394939000
_diffrn_orient_matrix_UB_22      -0.0638534000
_diffrn_orient_matrix_UB_23      0.0229157000
_diffrn_orient_matrix_UB_31      -0.0133478000
_diffrn_orient_matrix_UB_32      0.0197191000
_diffrn_orient_matrix_UB_33      0.0366493000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3050
_reflns_number_total             3862
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.410
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      0.911
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1284
_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:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00J(H00J), C00K(H00K),
 C00L(H00L)
2.d Idealised Me refined as rotating group:
 C00N(H00H,H00I,H00M)
;
_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 0.43546(3) 0.33797(6) 0.63872(2) 0.02203(14) Uani 1 1 d . . . . .
Cl02 Cl -0.01008(4) 0.73984(7) 0.27940(3) 0.03428(15) Uani 1 1 d . . . . .
O003 O 0.35068(9) 0.50230(16) 0.61995(7) 0.0212(3) Uani 1 1 d . . . . .
O004 O 0.21808(10) 0.77199(16) 0.67087(7) 0.0244(3) Uani 1 1 d . . . . .
O005 O 0.14842(10) 1.00803(17) 0.58741(8) 0.0298(3) Uani 1 1 d . . . . .
O006 O 0.42649(10) 0.22365(18) 0.70620(7) 0.0292(3) Uani 1 1 d . . . . .
O007 O 0.53094(9) 0.4357(2) 0.64645(7) 0.0298(3) Uani 1 1 d . . . . .
C008 C 0.13556(13) 0.7048(2) 0.52388(10) 0.0207(3) Uani 1 1 d . . . . .
C009 C 0.16564(13) 0.8404(2) 0.59523(10) 0.0226(3) Uani 1 1 d . . . . .
C00A C 0.17060(12) 0.5165(2) 0.53427(9) 0.0194(3) Uani 1 1 d . . . . .
C00B C 0.24204(12) 0.4571(2) 0.61835(10) 0.0208(3) Uani 1 1 d . . . . .
H00B H 0.234583 0.318250 0.627307 0.025 Uiso 1 1 calc R . . . .
C00C C 0.08497(13) 0.4621(3) 0.38724(10) 0.0258(4) Uani 1 1 d . . . . .
H00C H 0.065992 0.379254 0.340424 0.031 Uiso 1 1 calc R . . . .
C00D C 0.39753(13) 0.2045(3) 0.54655(10) 0.0225(3) Uani 1 1 d . . . . .
C00E C 0.07737(13) 0.7727(2) 0.44534(10) 0.0237(3) Uani 1 1 d . . . . .
H00E H 0.053448 0.900403 0.438281 0.028 Uiso 1 1 calc R . . . .
C00F C 0.38973(14) 0.2961(3) 0.47180(10) 0.0252(4) Uani 1 1 d . . . . .
H00F H 0.407357 0.426564 0.471234 0.030 Uiso 1 1 calc R . . . .
C00G C 0.14309(13) 0.3951(2) 0.46595(10) 0.0234(3) Uani 1 1 d . . . . .
H00G H 0.164008 0.265720 0.472944 0.028 Uiso 1 1 calc R . . . .
C00H C 0.22097(13) 0.5703(2) 0.68656(10) 0.0235(3) Uani 1 1 d . . . . .
H00A H 0.152862 0.530177 0.692219 0.028 Uiso 1 1 calc R . . . .
H00D H 0.276425 0.543046 0.740052 0.028 Uiso 1 1 calc R . . . .
C00I C 0.05521(13) 0.6512(3) 0.37817(10) 0.0241(4) Uani 1 1 d . . . . .
C00J C 0.37558(13) 0.0125(3) 0.54853(11) 0.0259(4) Uani 1 1 d . . . . .
H00J H 0.383310 -0.049672 0.600075 0.031 Uiso 1 1 calc R . . . .
C00K C 0.34219(14) -0.0870(3) 0.47401(12) 0.0299(4) Uani 1 1 d . . . . .
H00K H 0.327864 -0.218925 0.474763 0.036 Uiso 1 1 calc R . . . .
C00L C 0.35572(14) 0.1931(3) 0.39824(11) 0.0279(4) Uani 1 1 d . . . . .
H00L H 0.350472 0.254099 0.346906 0.034 Uiso 1 1 calc R . . . .
C00M C 0.32922(14) 0.0032(3) 0.39785(11) 0.0289(4) Uani 1 1 d . . . . .
C00N C 0.28591(16) -0.1019(3) 0.31645(13) 0.0404(5) Uani 1 1 d . . . . .
H00H H 0.285071 -0.238333 0.327485 0.061 Uiso 1 1 calc GR . . . .
H00I H 0.330279 -0.077431 0.281315 0.061 Uiso 1 1 calc GR . . . .
H00M H 0.214207 -0.058269 0.287597 0.061 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 O003 1.5832(12) . ?
S1 O006 1.4312(12) . ?
S1 O007 1.4236(13) . ?
S1 C00D 1.7501(17) . ?
Cl02 C00I 1.7353(16) . ?
O003 C00B 1.4842(19) . ?
O004 C009 1.337(2) . ?
O004 C00H 1.444(2) . ?
O005 C009 1.203(2) . ?
C008 C009 1.489(2) . ?
C008 C00A 1.400(2) . ?
C008 C00E 1.393(2) . ?
C00A C00B 1.499(2) . ?
C00A C00G 1.389(2) . ?
C00B C00H 1.500(2) . ?
C00C C00G 1.393(2) . ?
C00C C00I 1.385(3) . ?
C00D C00F 1.392(2) . ?
C00D C00J 1.387(3) . ?
C00E C00I 1.376(2) . ?
C00F C00L 1.385(2) . ?
C00J C00K 1.385(3) . ?
C00K C00M 1.395(3) . ?
C00L C00M 1.383(3) . ?
C00M C00N 1.506(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
O003 S1 C00D 103.13(7) . . ?
O006 S1 O003 109.53(7) . . ?
O006 S1 C00D 109.34(8) . . ?
O007 S1 O003 103.51(7) . . ?
O007 S1 O006 119.98(8) . . ?
O007 S1 C00D 109.92(8) . . ?
C00B O003 S1 119.10(10) . . ?
C009 O004 C00H 120.34(13) . . ?
C00A C008 C009 120.82(14) . . ?
C00E C008 C009 118.44(15) . . ?
C00E C008 C00A 120.62(15) . . ?
O004 C009 C008 117.84(14) . . ?
O005 C009 O004 118.89(15) . . ?
O005 C009 C008 123.20(15) . . ?
C008 C00A C00B 118.15(14) . . ?
C00G C00A C008 119.31(14) . . ?
C00G C00A C00B 122.44(14) . . ?
O003 C00B C00A 106.68(12) . . ?
O003 C00B C00H 107.19(12) . . ?
C00A C00B C00H 111.05(13) . . ?
C00I C00C C00G 119.08(16) . . ?
C00F C00D S1 118.30(14) . . ?
C00J C00D S1 120.45(13) . . ?
C00J C00D C00F 121.24(16) . . ?
C00I C00E C008 118.71(16) . . ?
C00L C00F C00D 118.60(17) . . ?
C00A C00G C00C 120.30(16) . . ?
O004 C00H C00B 112.53(13) . . ?
C00C C00I Cl02 119.50(13) . . ?
C00E C00I Cl02 118.64(13) . . ?
C00E C00I C00C 121.86(15) . . ?
C00K C00J C00D 118.80(16) . . ?
C00J C00K C00M 121.11(17) . . ?
C00M C00L C00F 121.48(17) . . ?
C00K C00M C00N 121.08(18) . . ?
C00L C00M C00K 118.65(16) . . ?
C00L C00M C00N 120.26(18) . . ?

_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 1.207
_oxdiff_exptl_absorpt_empirical_full_min 0.778
####################################################################### 
# 
# 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_644
_database_code_depnum_ccdc_archive 'CCDC 2044380'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 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     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 F3 O5 S'
_chemical_formula_sum            'C17 H13 F3 O5 S'
_chemical_formula_weight         386.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H13 F3 O5 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.2174(3)
_cell_length_b                   7.3404(2)
_cell_length_c                   15.8342(6)
_cell_angle_alpha                97.483(3)
_cell_angle_beta                 102.711(3)
_cell_angle_gamma                92.093(3)
_cell_volume                     809.50(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7693
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.0700
_cell_measurement_theta_min      5.7510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (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_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12405
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.225
_diffrn_reflns_theta_min         5.788
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -51.00   0.50    0.12    --  -42.80-154.00 171.00   72
  2  ω    -79.00 -53.00   0.50    0.12    --  -42.80 120.00  53.00   52
  3  ω    -48.00  -8.00   0.50    0.12    --  -42.80 120.00  53.00   80
  4  ω    -93.00 -68.00   0.50    0.12    --  -42.80 154.00-148.00   50
  5  ω     60.00 107.00   0.50    0.12    --   42.80 154.00-148.00   94
  6  ω     53.00  92.00   0.50    0.12    --   42.80-154.00 171.00   78
  7  ω      7.00  92.00   0.50    0.12    --   42.80-120.00 -30.00  170
  8  ω     88.00 113.00   0.50    0.48    --   76.50 120.00  53.00   50
  9  ω     77.00 102.00   0.50    0.48    --   76.50 154.00-148.00   50
 10  ω     36.00  61.00   0.50    0.48    --   76.50-120.00 -30.00   50
 11  ω   -133.00-108.00   0.50    0.48    -- -106.00-154.00 171.00   50
 12  ω    -84.00 -59.00   0.50    0.48    -- -106.00 154.00-148.00   50
 13  ω   -101.00 -75.00   0.50    0.48    -- -106.00 120.00  53.00   52
 14  ω   -150.00-125.00   0.50    0.48    -- -106.00-120.00 -30.00   50
 15  ω   -116.00 -16.00   0.50    0.12    --  -42.80 -77.00 -90.00  200
 16  ω     57.00 115.00   0.50    0.12    --   42.80  77.00-180.00  116
 17  ω     16.00  53.00   0.50    0.12    --   42.80  77.00-180.00   74
 18  ω     47.00 146.00   0.50    0.48    --   76.50  19.00-150.00  198
 19  ω     57.00  82.00   0.50    0.48    --   76.50-154.00 171.00   50
 20  ω   -117.00 -72.00   0.50    0.48    -- -106.00 125.00 -60.00   90
 21  ω    -84.00 -33.00   0.50    0.48    -- -106.00 125.00-150.00  102
 22  ω   -113.00 -88.00   0.50    0.48    -- -106.00 125.00 120.00   50
 23  ω   -115.00 -89.00   0.50    0.48    -- -106.00 125.00-150.00   52
 24  ω   -121.00 -83.00   0.50    0.48    -- -106.00 -57.00  30.00   76
 25  ω   -116.00 -60.00   0.50    0.48    -- -106.00 125.00-180.00  112
 26  ω   -170.00-130.00   0.50    0.48    -- -106.00-125.00   0.00   80
 27  ω   -111.00 -71.00   0.50    0.48    -- -106.00-125.00   0.00   80
 28  ω   -176.00-132.00   0.50    0.48    -- -106.00 -57.00 150.00   88
 29  ω   -112.00 -80.00   0.50    0.48    -- -106.00 -77.00  90.00   64
 30  ω   -172.00-123.00   0.50    0.48    -- -106.00-125.00  60.00   98
 31  ω   -120.00 -94.00   0.50    0.48    -- -106.00  77.00 150.00   52
 32  ω   -174.00-133.00   0.50    0.48    -- -106.00 -57.00  30.00   82
 33  ω   -108.00 -81.00   0.50    0.48    -- -106.00-125.00  60.00   54
 34  ω   -147.00 -78.00   0.50    0.48    -- -106.00 -22.00  34.96  138
 35  ω   -129.00-104.00   0.50    0.48    -- -106.00  77.00 -90.00   50
 36  ω   -118.00 -54.00   0.50    0.48    -- -106.00  57.00   0.00  128
 37  ω    -92.00 -42.00   0.50    0.48    -- -106.00  77.00-150.00  100
 38  ω   -100.00 -46.00   0.50    0.48    -- -106.00  57.00-150.00  108
 39  ω   -131.00-105.00   0.50    0.48    -- -106.00  28.00-120.67   52
 40  ω    -99.00 -73.00   0.50    0.48    -- -106.00  28.00-120.67   52
 41  ω   -174.00-111.00   0.50    0.48    -- -106.00-125.00 -90.00  126
 42  ω    -96.00 -33.00   0.50    0.48    -- -106.00 125.00 -90.00  126
 43  ω   -113.00 -77.00   0.50    0.48    -- -106.00 -19.00  90.00   72
 44  ω   -157.00-132.00   0.50    0.48    -- -106.00 -19.00  90.00   50
 45  ω    -92.00 -41.00   0.50    0.48    -- -106.00 125.00 -30.00  102
 46  ω    -67.00 -34.00   0.50    0.48    -- -106.00 125.00 -60.00   66
 47  ω   -109.00 -84.00   0.50    0.48    -- -106.00  98.00-115.24   50
 48  ω   -100.00 -74.00   0.50    0.48    -- -106.00 125.00  30.00   52
 49  ω   -104.00 -32.00   0.50    0.48    -- -106.00 125.00  60.00  144
 50  ω   -122.00 -93.00   0.50    0.48    -- -106.00 136.00 -79.96   58
 51  ω    -62.00 -34.00   0.50    0.48    -- -106.00 136.00 -79.96   56
 52  ω   -175.00-140.00   0.50    0.48    -- -106.00 -99.00  90.00   70
 53  ω   -111.00 -83.00   0.50    0.48    -- -106.00  58.00  66.59   56
 54  ω   -117.00 -91.00   0.50    0.48    -- -106.00  60.00 156.85   52
 55  ω    -61.00 -36.00   0.50    0.48    -- -106.00  60.00 156.85   50
 56  ω   -119.00 -93.00   0.50    0.48    -- -106.00  65.00 -26.04   52
 57  ω   -145.00-119.00   0.50    0.48    -- -106.00 -77.00  90.00   52
 58  ω   -175.00 -86.00   0.50    0.48    -- -106.00 -37.00-150.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0777746000
_diffrn_orient_matrix_UB_12      0.0713256000
_diffrn_orient_matrix_UB_13      0.0978274000
_diffrn_orient_matrix_UB_21      -0.0088803000
_diffrn_orient_matrix_UB_22      -0.1987684000
_diffrn_orient_matrix_UB_23      0.0210568000
_diffrn_orient_matrix_UB_31      0.2048648000
_diffrn_orient_matrix_UB_32      -0.0203888000
_diffrn_orient_matrix_UB_33      -0.0117554000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3134
_reflns_number_total             3273
_reflns_odcompleteness_completeness 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0051P)²+1.9751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1323
_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:
 C0BA(H0BA)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2AA(H2AA), C7AA(H7AA), C1BA(H1BA), C3BA(H3BA), C(H), C1(H1), C2(H2)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S0AA S 0.10733(11) 0.44965(10) 0.18704(5) 0.02667(19) Uani 1 1 d . . . . .
O3 O 0.1949(3) 0.3381(3) 0.26421(12) 0.0248(4) Uani 1 1 d . . . . .
F0AA F 0.0498(3) 0.2128(3) 0.62265(14) 0.0443(5) Uani 1 1 d . . . . .
O4 O 0.4372(3) 0.0431(3) 0.29164(14) 0.0275(5) Uani 1 1 d . . . . .
F1AA F 0.0817(4) 0.4868(3) 0.59947(16) 0.0525(6) Uani 1 1 d . . . . .
O0AA O 0.1879(4) 0.6333(3) 0.21882(15) 0.0368(6) Uani 1 1 d . . . . .
O1AA O 0.7468(3) 0.1227(3) 0.34929(16) 0.0360(5) Uani 1 1 d . . . . .
O2AA O -0.0937(3) 0.4127(4) 0.16354(15) 0.0403(6) Uani 1 1 d . . . . .
C2AA C 0.2024(4) 0.1992(4) 0.47137(18) 0.0209(6) Uani 1 1 d . . . . .
H2AA H 0.068127 0.174976 0.456556 0.025 Uiso 1 1 calc R . . . .
C3AA C 0.5857(4) 0.1195(4) 0.3582(2) 0.0262(6) Uani 1 1 d . . . . .
C4AA C 0.3132(4) 0.1507(4) 0.41175(18) 0.0195(5) Uani 1 1 d . . . . .
C10 C 0.1211(4) 0.1480(4) 0.25587(19) 0.0266(6) Uani 1 1 d . . . . .
H10A H 0.109560 0.085933 0.195375 0.032 Uiso 1 1 calc R . . . .
H10B H -0.006321 0.143435 0.269437 0.032 Uiso 1 1 calc R . . . .
C5AA C 0.2976(4) 0.2851(4) 0.55411(18) 0.0207(6) Uani 1 1 d . . . . .
F F 0.2864(3) 0.3869(5) 0.70001(14) 0.0836(11) Uani 1 1 d . . . . .
C7AA C 0.4947(4) 0.3214(4) 0.57701(19) 0.0241(6) Uani 1 1 d . . . . .
H7AA H 0.554887 0.379266 0.634208 0.029 Uiso 1 1 calc R . . . .
C8AA C 0.5077(4) 0.1871(4) 0.43421(19) 0.0207(6) Uani 1 1 d . . . . .
C9AA C 0.2047(4) 0.3549(4) 0.10050(18) 0.0246(6) Uani 1 1 d . . . . .
C0BA C 0.2575(4) 0.0539(4) 0.31889(18) 0.0235(6) Uani 1 1 d . . . . .
H0BA H 0.203330 -0.073469 0.318764 0.028 Uiso 1 1 calc R . . . .
C1BA C 0.0852(5) 0.2803(5) 0.0213(2) 0.0357(7) Uani 1 1 d . . . . .
H1BA H -0.048986 0.275451 0.014709 0.043 Uiso 1 1 calc R . . . .
C2BA C 0.3575(6) 0.2187(6) -0.0398(2) 0.0427(9) Uani 1 1 d . . . . .
C3BA C 0.6027(4) 0.2730(4) 0.51628(19) 0.0244(6) Uani 1 1 d . . . . .
H3BA H 0.736894 0.297796 0.530392 0.029 Uiso 1 1 calc R . . . .
C4BA C 0.1820(4) 0.3432(4) 0.61952(19) 0.0285(7) Uani 1 1 d . . . . .
C C 0.1630(5) 0.2132(5) -0.0478(2) 0.0384(8) Uani 1 1 d . . . . .
H H 0.080999 0.162071 -0.101921 0.046 Uiso 1 1 calc R . . . .
C1 C 0.3995(5) 0.3617(6) 0.1102(2) 0.0463(10) Uani 1 1 d . . . . .
H1 H 0.481604 0.412613 0.164303 0.056 Uiso 1 1 calc R . . . .
C2 C 0.4735(6) 0.2931(8) 0.0398(3) 0.0640(14) Uani 1 1 d . . . . .
H2 H 0.607715 0.297337 0.046340 0.077 Uiso 1 1 calc R . . . .
C3 C 0.4407(8) 0.1484(8) -0.1168(3) 0.0699(15) Uani 1 1 d . . . . .
H3A H 0.392369 0.020625 -0.138876 0.105 Uiso 1 1 calc GR . . . .
H3B H 0.579832 0.154070 -0.098093 0.105 Uiso 1 1 calc GR . . . .
H3C H 0.403798 0.224933 -0.163276 0.105 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
S0AA O3 1.588(2) . ?
S0AA O0AA 1.430(2) . ?
S0AA O2AA 1.423(2) . ?
S0AA C9AA 1.751(3) . ?
O3 C10 1.455(4) . ?
F0AA C4BA 1.340(4) . ?
O4 C3AA 1.371(4) . ?
O4 C0BA 1.456(3) . ?
F1AA C4BA 1.333(4) . ?
O1AA C3AA 1.201(4) . ?
C2AA C4AA 1.387(4) . ?
C2AA C5AA 1.394(4) . ?
C3AA C8AA 1.475(4) . ?
C4AA C8AA 1.377(4) . ?
C4AA C0BA 1.508(4) . ?
C10 C0BA 1.496(4) . ?
C5AA C7AA 1.395(4) . ?
C5AA C4BA 1.498(4) . ?
F C4BA 1.322(4) . ?
C7AA C3BA 1.385(4) . ?
C8AA C3BA 1.385(4) . ?
C9AA C1BA 1.388(4) . ?
C9AA C1 1.378(5) . ?
C1BA C 1.380(5) . ?
C2BA C 1.380(5) . ?
C2BA C2 1.382(5) . ?
C2BA C3 1.515(5) . ?
C1 C2 1.385(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S0AA C9AA 103.69(13) . . ?
O0AA S0AA O3 103.29(12) . . ?
O0AA S0AA C9AA 109.95(15) . . ?
O2AA S0AA O3 109.16(14) . . ?
O2AA S0AA O0AA 120.33(15) . . ?
O2AA S0AA C9AA 109.05(14) . . ?
C10 O3 S0AA 116.51(17) . . ?
C3AA O4 C0BA 110.9(2) . . ?
C4AA C2AA C5AA 116.8(3) . . ?
O4 C3AA C8AA 108.0(2) . . ?
O1AA C3AA O4 121.4(3) . . ?
O1AA C3AA C8AA 130.6(3) . . ?
C2AA C4AA C0BA 130.4(3) . . ?
C8AA C4AA C2AA 120.9(3) . . ?
C8AA C4AA C0BA 108.7(2) . . ?
O3 C10 C0BA 107.6(2) . . ?
C2AA C5AA C7AA 122.4(3) . . ?
C2AA C5AA C4BA 118.2(3) . . ?
C7AA C5AA C4BA 119.4(3) . . ?
C3BA C7AA C5AA 120.0(3) . . ?
C4AA C8AA C3AA 108.4(3) . . ?
C4AA C8AA C3BA 122.5(3) . . ?
C3BA C8AA C3AA 129.1(3) . . ?
C1BA C9AA S0AA 119.8(2) . . ?
C1 C9AA S0AA 119.8(2) . . ?
C1 C9AA C1BA 120.3(3) . . ?
O4 C0BA C4AA 103.9(2) . . ?
O4 C0BA C10 109.2(2) . . ?
C10 C0BA C4AA 116.1(2) . . ?
C C1BA C9AA 119.5(3) . . ?
C C2BA C2 118.1(3) . . ?
C C2BA C3 120.7(4) . . ?
C2 C2BA C3 121.1(4) . . ?
C7AA C3BA C8AA 117.5(3) . . ?
F0AA C4BA C5AA 112.8(2) . . ?
F1AA C4BA F0AA 103.9(3) . . ?
F1AA C4BA C5AA 112.1(3) . . ?
F C4BA F0AA 106.7(3) . . ?
F C4BA F1AA 107.8(3) . . ?
F C4BA C5AA 113.0(3) . . ?
C1BA C C2BA 121.3(3) . . ?
C9AA C1 C2 119.0(3) . . ?
C2BA C2 C1 121.8(4) . . ?

_olex2_submission_original_sample_id 641
_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 1.747
_oxdiff_exptl_absorpt_empirical_full_min 0.629
####################################################################### 
# 
# 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_xcalibur_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2044382'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C17 H16 O5 S'
_chemical_formula_moiety         'C17 H16 O5 S'
_chemical_formula_weight         332.37
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.08417(16)
_cell_length_b                   7.1589(2)
_cell_length_c                   15.9037(4)
_cell_angle_alpha                97.204(2)
_cell_angle_beta                 101.828(2)
_cell_angle_gamma                96.290(2)
_cell_volume                     775.56(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6186
_cell_measurement_theta_min      6.26
_cell_measurement_theta_max      73.65
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_colour            nONE
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348.00
_exptl_absorpt_coefficient_mu    2.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            11729
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_theta_max         74.20
_diffrn_reflns_theta_min         5.752
_diffrn_reflns_theta_full        74.20
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3118
_reflns_number_gt                2822
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 2.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2822
_refine_ls_number_parameters     224
_refine_ls_goodness_of_fit_ref   2.435
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     'w = 1/σ²(Fo²)'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.388
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.38229(6) 0.03863(6) 0.80809(2) 0.02761(11) Uani 1 2 d . . .
O2 O 0.41306(16) 0.15210(16) 0.73178(7) 0.0276(3) Uani 1 2 d . . .
O3 O 0.20311(17) 0.0724(2) 0.83080(8) 0.0370(3) Uani 1 2 d . . .
O4 O 0.65823(17) 0.46916(18) 0.69961(8) 0.0319(3) Uani 1 2 d . . .
O5 O 0.91358(17) 0.4019(2) 0.64414(9) 0.0423(4) Uani 1 2 d . . .
O6 O 0.4116(2) -0.14949(18) 0.77771(8) 0.0375(3) Uani 1 2 d . . .
C7 C 0.4060(2) 0.3361(2) 0.58103(10) 0.0241(4) Uani 1 2 d . . .
C8 C 0.4176(3) 0.1617(2) 0.41825(11) 0.0303(4) Uani 1 2 d . . .
C9 C 0.5817(2) 0.3121(2) 0.55967(10) 0.0257(4) Uani 1 2 d . . .
C10 C 0.5748(2) 0.1412(2) 0.89536(10) 0.0260(4) Uani 1 2 d . . .
C11 C 0.5915(3) 0.2249(2) 0.47788(11) 0.0298(4) Uani 1 2 d . . .
C12 C 0.2379(2) 0.1829(2) 0.43882(10) 0.0280(4) Uani 1 2 d . . .
C13 C 0.2306(2) 0.2720(2) 0.52138(10) 0.0261(4) Uani 1 2 d . . .
C14 C 0.4467(2) 0.4417(2) 0.67225(10) 0.0271(4) Uani 1 2 d . . .
C15 C 0.8794(3) 0.2854(3) 1.03738(12) 0.0390(5) Uani 1 2 d . . .
C16 C 0.7400(2) 0.3941(3) 0.63483(11) 0.0303(4) Uani 1 2 d . . .
C17 C 0.6904(3) 0.3048(3) 1.04049(11) 0.0380(5) Uani 1 2 d . . .
C18 C 0.3625(2) 0.3448(2) 0.73767(10) 0.0289(4) Uani 1 2 d . . .
C19 C 0.0523(3) 0.1130(3) 0.37143(12) 0.0403(5) Uani 1 2 d . . .
C20 C 0.5361(3) 0.2341(3) 0.97027(11) 0.0349(4) Uani 1 2 d . . .
C21 C 0.7638(3) 0.1215(3) 0.88965(12) 0.0421(5) Uani 1 2 d . . .
C22 C 0.9142(3) 0.1933(4) 0.96105(14) 0.0526(6) Uani 1 2 d . . .
C23 C 1.0432(4) 0.3565(4) 1.11584(15) 0.0585(7) Uani 1 2 d . . .
H1 H 0.42018 0.10275 0.36303 0.0360 Uiso 1 2 calc R . .
H2 H 0.71041 0.21036 0.46353 0.0372 Uiso 1 2 calc R . .
H3 H 0.11181 0.28717 0.53573 0.0305 Uiso 1 2 calc R . .
H4 H 0.40263 0.56653 0.67067 0.0311 Uiso 1 2 calc R . .
H5 H 0.66426 0.36721 1.09087 0.0443 Uiso 1 2 calc R . .
H6 H 0.22168 0.3369 0.7247 0.0339 Uiso 1 2 calc R . .
H7 H 0.41519 0.41017 0.79643 0.0346 Uiso 1 2 calc R . .
H8 H -0.01785 0.21758 0.35957 0.0458 Uiso 1 2 calc R . .
H9 H 0.08418 0.05636 0.31906 0.0460 Uiso 1 2 calc R . .
H10 H -0.02726 0.0199 0.39232 0.0459 Uiso 1 2 calc R . .
H11 H 0.40886 0.24847 0.9736 0.0411 Uiso 1 2 calc R . .
H12 H 0.79027 0.06172 0.8388 0.0499 Uiso 1 2 calc R . .
H13 H 1.04136 0.17933 0.95746 0.0617 Uiso 1 2 calc R . .
H14 H 1.13684 0.44721 1.1013 0.0661 Uiso 1 2 calc R . .
H15 H 0.9919 0.41577 1.16225 0.0660 Uiso 1 2 calc R . .
H16 H 1.10498 0.25099 1.13401 0.0662 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
S1 O2 1.5802(13) yes .
S1 O3 1.4260(14) yes .
S1 O6 1.4246(14) yes .
S1 C10 1.7536(14) yes .
O2 C18 1.459(2) yes .
O4 C14 1.4558(19) yes .
O4 C16 1.364(2) yes .
O5 C16 1.202(2) yes .
C7 C9 1.378(2) yes .
C7 C13 1.392(2) yes .
C7 C14 1.505(2) yes .
C8 C11 1.383(2) yes .
C8 C12 1.397(3) yes .
C9 C11 1.389(2) yes .
C9 C16 1.470(2) yes .
C10 C20 1.383(2) yes .
C10 C21 1.382(3) yes .
C12 C13 1.400(2) yes .
C12 C19 1.507(2) yes .
C14 C18 1.505(3) yes .
C15 C17 1.372(3) yes .
C15 C22 1.388(3) yes .
C15 C23 1.510(3) yes .
C17 C20 1.391(2) yes .
C21 C22 1.388(3) yes .
C8 H1 0.930 no .
C11 H2 0.930 no .
C13 H3 0.930 no .
C14 H4 0.980 no .
C17 H5 0.930 no .
C18 H6 0.970 no .
C18 H7 0.970 no .
C19 H8 0.960 no .
C19 H9 0.960 no .
C19 H10 0.960 no .
C20 H11 0.930 no .
C21 H12 0.930 no .
C22 H13 0.930 no .
C23 H14 0.960 no .
C23 H15 0.960 no .
C23 H16 0.960 no .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 S1 O3 109.26(8) yes . .
O2 S1 O6 103.65(7) yes . .
O2 S1 C10 104.24(7) yes . .
O3 S1 O6 120.20(9) yes . .
O3 S1 C10 108.70(8) yes . .
O6 S1 C10 109.58(8) yes . .
S1 O2 C18 116.66(10) yes . .
C14 O4 C16 110.94(12) yes . .
C9 C7 C13 121.10(15) yes . .
C9 C7 C14 108.19(12) yes . .
C13 C7 C14 130.67(16) yes . .
C11 C8 C12 121.81(16) yes . .
C7 C9 C11 121.61(14) yes . .
C7 C9 C16 108.83(14) yes . .
C11 C9 C16 129.55(16) yes . .
S1 C10 C20 119.94(13) yes . .
S1 C10 C21 119.34(13) yes . .
C20 C10 C21 120.67(14) yes . .
C8 C11 C9 117.51(17) yes . .
C8 C12 C13 119.98(14) yes . .
C8 C12 C19 119.89(15) yes . .
C13 C12 C19 120.12(16) yes . .
C7 C13 C12 117.99(16) yes . .
O4 C14 C7 104.10(13) yes . .
O4 C14 C18 108.78(13) yes . .
C7 C14 C18 116.98(13) yes . .
C17 C15 C22 117.94(16) yes . .
C17 C15 C23 120.71(19) yes . .
C22 C15 C23 121.32(19) yes . .
O4 C16 O5 121.57(14) yes . .
O4 C16 C9 107.92(14) yes . .
O5 C16 C9 130.51(17) yes . .
C15 C17 C20 121.87(18) yes . .
O2 C18 C14 107.67(14) yes . .
C10 C20 C17 118.94(18) yes . .
C10 C21 C22 118.85(19) yes . .
C15 C22 C21 121.7(2) yes . .
C11 C8 H1 119.182 no . .
C12 C8 H1 119.008 no . .
C8 C11 H2 121.169 no . .
C9 C11 H2 121.322 no . .
C7 C13 H3 121.309 no . .
C12 C13 H3 120.703 no . .
O4 C14 H4 108.637 no . .
C7 C14 H4 109.028 no . .
C18 C14 H4 108.998 no . .
C15 C17 H5 119.225 no . .
C20 C17 H5 118.907 no . .
O2 C18 H6 108.501 no . .
O2 C18 H7 108.779 no . .
C14 C18 H6 110.753 no . .
C14 C18 H7 111.645 no . .
H6 C18 H7 109.408 no . .
C12 C19 H8 109.805 no . .
C12 C19 H9 108.968 no . .
C12 C19 H10 109.724 no . .
H8 C19 H9 109.439 no . .
H8 C19 H10 109.444 no . .
H9 C19 H10 109.447 no . .
C10 C20 H11 120.406 no . .
C17 C20 H11 120.655 no . .
C10 C21 H12 120.738 no . .
C22 C21 H12 120.413 no . .
C15 C22 H13 119.315 no . .
C21 C22 H13 118.956 no . .
C15 C23 H14 109.793 no . .
C15 C23 H15 109.606 no . .
C15 C23 H16 109.097 no . .
H14 C23 H15 109.444 no . .
H14 C23 H16 109.444 no . .
H15 C23 H16 109.443 no . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 S1 O2 C18 41.39(9) no . . . .
O6 S1 O2 C18 170.67(8) no . . . .
O2 S1 C10 C20 116.91(12) no . . . .
O2 S1 C10 C21 -65.70(13) no . . . .
C10 S1 O2 C18 -74.66(9) no . . . .
O3 S1 C10 C20 0.47(15) no . . . .
O3 S1 C10 C21 177.87(11) no . . . .
O6 S1 C10 C20 -132.69(12) no . . . .
O6 S1 C10 C21 44.71(15) no . . . .
S1 O2 C18 C14 166.52(7) no . . . .
C14 O4 C16 O5 179.95(15) no . . . .
C14 O4 C16 C9 0.19(18) no . . . .
C16 O4 C14 C7 0.69(17) no . . . .
C16 O4 C14 C18 126.10(13) no . . . .
C9 C7 C13 C12 -0.2(2) no . . . .
C13 C7 C9 C11 0.5(2) no . . . .
C13 C7 C9 C16 179.72(14) no . . . .
C9 C7 C14 O4 -1.37(17) no . . . .
C9 C7 C14 C18 -121.38(15) no . . . .
C14 C7 C9 C11 -177.67(13) no . . . .
C14 C7 C9 C16 1.52(18) no . . . .
C13 C7 C14 O4 -179.33(16) no . . . .
C13 C7 C14 C18 60.7(2) no . . . .
C14 C7 C13 C12 177.58(15) no . . . .
C11 C8 C12 C13 0.7(3) no . . . .
C11 C8 C12 C19 179.54(15) no . . . .
C12 C8 C11 C9 -0.4(3) no . . . .
C7 C9 C11 C8 -0.3(2) no . . . .
C7 C9 C16 O4 -1.10(19) no . . . .
C7 C9 C16 O5 179.17(18) no . . . .
C11 C9 C16 O4 178.00(16) no . . . .
C11 C9 C16 O5 -1.7(3) no . . . .
C16 C9 C11 C8 -179.26(16) no . . . .
S1 C10 C20 C17 176.32(11) no . . . .
S1 C10 C21 C22 -176.19(13) no . . . .
C20 C10 C21 C22 1.2(3) no . . . .
C21 C10 C20 C17 -1.0(3) no . . . .
C8 C12 C13 C7 -0.5(2) no . . . .
C19 C12 C13 C7 -179.26(15) no . . . .
O4 C14 C18 O2 -67.75(14) no . . . .
C7 C14 C18 O2 49.75(17) no . . . .
C17 C15 C22 C21 -0.3(4) no . . . .
C22 C15 C17 C20 0.5(3) no . . . .
C23 C15 C17 C20 -177.52(19) no . . . .
C23 C15 C22 C21 177.7(2) no . . . .
C15 C17 C20 C10 0.2(3) no . . . .
C10 C21 C22 C15 -0.5(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O2 O4 2.8674(17) no . .
O2 C7 2.871(2) no . .
O2 C9 3.473(2) no . .
O2 C13 3.5770(19) no . .
O2 C16 3.464(2) no . .
O2 C21 3.198(2) no . .
O3 C18 2.863(2) no . .
O3 C20 2.9048(19) no . .
O5 C7 3.4913(19) no . .
O5 C11 3.1395(19) no . .
O5 C14 3.464(2) no . .
O6 C21 3.068(2) no . .
C7 C8 2.751(2) no . .
C9 C12 2.761(2) no . .
C9 C18 3.492(2) no . .
C10 C15 2.784(2) no . .
C10 C18 3.244(2) no . .
C11 C13 2.825(3) no . .
C13 C18 3.332(2) no . .
C16 C18 3.418(3) no . .
C17 C21 2.760(3) no . .
C20 C22 2.757(3) no . .
O2 C8 3.549(2) no . 2_656
O2 C19 3.577(2) no . 2_556
O3 C15 3.580(3) no . 2_657
O3 C19 3.376(2) no . 2_556
O3 C21 3.469(2) no . 1_455
O3 C22 3.303(3) no . 1_455
O4 C8 3.454(2) no . 2_666
O4 C23 3.256(2) no . 2_767
O5 C12 3.582(2) no . 2_666
O5 C13 3.394(2) no . 1_655
O5 C18 3.315(2) no . 1_655
O5 C19 3.498(3) no . 2_666
O6 C8 3.562(2) no . 2_656
O6 C14 3.247(2) no . 1_545
O6 C17 3.406(2) no . 2_657
O6 C18 3.562(2) no . 1_545
C7 C9 3.578(2) no . 2_666
C7 C11 3.389(2) no . 2_666
C8 O2 3.549(2) no . 2_656
C8 O4 3.454(2) no . 2_666
C8 O6 3.562(2) no . 2_656
C8 C9 3.454(2) no . 2_656
C8 C11 3.398(3) no . 2_656
C8 C14 3.471(3) no . 2_666
C9 C7 3.578(2) no . 2_666
C9 C8 3.454(2) no . 2_656
C11 C7 3.389(2) no . 2_666
C11 C8 3.398(3) no . 2_656
C11 C11 3.546(2) no . 2_656
C11 C12 3.581(2) no . 2_656
C11 C14 3.574(3) no . 2_666
C12 O5 3.582(2) no . 2_666
C12 C11 3.581(2) no . 2_656
C12 C16 3.381(3) no . 2_666
C13 O5 3.394(2) no . 1_455
C14 O6 3.247(2) no . 1_565
C14 C8 3.471(3) no . 2_666
C14 C11 3.574(3) no . 2_666
C15 O3 3.580(3) no . 2_657
C16 C12 3.381(3) no . 2_666
C17 O6 3.406(2) no . 2_657
C18 O5 3.315(2) no . 1_455
C18 O6 3.562(2) no . 1_565
C19 O2 3.577(2) no . 2_556
C19 O3 3.376(2) no . 2_556
C19 O5 3.498(3) no . 2_666
C21 O3 3.469(2) no . 1_655
C22 O3 3.303(3) no . 1_655
C22 C22 3.414(4) no . 2_757
C22 C23 3.591(4) no . 2_767
C23 O4 3.256(2) no . 2_767
C23 C22 3.591(4) no . 2_767
S1 H6 2.8700 no . .
S1 H7 2.6775 no . .
S1 H11 2.8220 no . .
S1 H12 2.8135 no . .
O2 H4 3.2395 no . .
O2 H12 3.0409 no . .
O3 H6 2.6995 no . .
O3 H7 2.8766 no . .
O3 H11 2.5285 no . .
O4 H6 3.2525 no . .
O4 H7 2.5699 no . .
O5 H2 3.0144 no . .
O6 H12 2.8462 no . .
C7 H2 3.2569 no . .
C7 H6 2.8544 no . .
C7 H7 3.3862 no . .
C8 H3 3.2643 no . .
C8 H8 3.1195 no . .
C8 H9 2.5338 no . .
C8 H10 3.1295 no . .
C9 H1 3.2122 no . .
C9 H3 3.2545 no . .
C9 H4 2.9429 no . .
C10 H5 3.2238 no . .
C10 H7 2.8229 no . .
C10 H13 3.2202 no . .
C12 H2 3.2701 no . .
C13 H1 3.2544 no . .
C13 H4 2.9261 no . .
C13 H6 3.2232 no . .
C13 H8 2.7593 no . .
C13 H9 3.2936 no . .
C13 H10 2.7604 no . .
C14 H3 2.8772 no . .
C15 H11 3.2506 no . .
C15 H12 3.2602 no . .
C16 H2 2.8290 no . .
C16 H4 2.9308 no . .
C17 H13 3.2049 no . .
C17 H14 3.1259 no . .
C17 H15 2.5477 no . .
C17 H16 3.0965 no . .
C18 H3 3.2874 no . .
C19 H1 2.6455 no . .
C19 H3 2.6789 no . .
C20 H7 3.1790 no . .
C20 H12 3.2432 no . .
C21 H7 3.5993 no . .
C21 H11 3.2411 no . .
C22 H5 3.2066 no . .
C22 H14 2.7711 no . .
C22 H15 3.2993 no . .
C22 H16 2.7628 no . .
C23 H5 2.6427 no . .
C23 H13 2.6713 no . .
H1 H2 2.3178 no . .
H1 H8 3.2876 no . .
H1 H9 2.3133 no . .
H1 H10 3.2983 no . .
H3 H4 3.0096 no . .
H3 H6 2.9114 no . .
H3 H8 2.7268 no . .
H3 H9 3.5871 no . .
H3 H10 2.7212 no . .
H4 H6 2.3298 no . .
H4 H7 2.4024 no . .
H5 H11 2.3144 no . .
H5 H14 3.3003 no . .
H5 H15 2.3326 no . .
H5 H16 3.2779 no . .
H7 H11 3.1843 no . .
H12 H13 2.3090 no . .
H13 H14 2.7110 no . .
H13 H15 3.5792 no . .
H13 H16 2.7238 no . .
S1 H1 3.4014 no . 2_656
S1 H5 3.5086 no . 2_657
S1 H8 3.4718 no . 2_556
S1 H9 3.4489 no . 2_556
S1 H10 3.5788 no . 2_556
O2 H1 2.7405 no . 2_656
O2 H8 3.5634 no . 2_556
O2 H9 3.5591 no . 2_556
O2 H10 3.0533 no . 2_556
O3 H8 3.3758 no . 2_556
O3 H9 2.7788 no . 2_556
O3 H10 3.4640 no . 2_556
O3 H12 2.9464 no . 1_455
O3 H13 2.5900 no . 1_455
O3 H16 3.1867 no . 2_657
O4 H1 3.4066 no . 2_666
O4 H8 3.5589 no . 2_666
O4 H14 3.1529 no . 2_767
O4 H15 2.9180 no . 2_767
O4 H16 3.1533 no . 2_767
O5 H3 2.5513 no . 1_655
O5 H4 3.4571 no . 1_655
O5 H6 2.4181 no . 1_655
O5 H8 2.7547 no . 2_666
O5 H9 3.4049 no . 2_656
O5 H10 3.2228 no . 2_656
O5 H15 3.0966 no . 2_767
O6 H1 2.7814 no . 2_656
O6 H4 2.4687 no . 1_545
O6 H5 2.8601 no . 2_657
O6 H7 3.2057 no . 1_545
O6 H8 3.1182 no . 2_556
C7 H2 3.5566 no . 2_666
C8 H2 3.5884 no . 2_656
C8 H4 2.8797 no . 2_666
C9 H1 3.3537 no . 2_656
C10 H14 3.3843 no . 2_767
C11 H3 3.5748 no . 1_655
C11 H4 2.9536 no . 2_666
C12 H2 3.3998 no . 2_656
C13 H2 3.5742 no . 1_455
C13 H2 3.5555 no . 2_656
C13 H10 3.0328 no . 2_556
C14 H1 3.4411 no . 2_666
C15 H13 3.4419 no . 2_757
C15 H14 3.0897 no . 2_767
C16 H3 3.4421 no . 1_655
C16 H6 3.5081 no . 1_655
C16 H8 3.2055 no . 2_666
C16 H15 3.4195 no . 2_767
C17 H7 3.3544 no . 2_667
C17 H11 3.3735 no . 2_667
C17 H14 3.3757 no . 2_767
C18 H5 3.2573 no . 2_667
C18 H10 3.4647 no . 2_556
C19 H2 3.1724 no . 1_455
C19 H3 3.5737 no . 2_556
C19 H6 3.5574 no . 2_556
C20 H5 3.4822 no . 2_667
C20 H13 3.4449 no . 1_455
C20 H14 3.5273 no . 2_767
C21 H14 3.0695 no . 2_767
C21 H16 2.9240 no . 2_757
C22 H11 3.4450 no . 1_655
C22 H13 3.1275 no . 2_757
C22 H14 2.9038 no . 2_767
C22 H16 3.3224 no . 2_757
C23 H12 3.4417 no . 2_757
H1 S1 3.4014 no . 2_656
H1 O2 2.7405 no . 2_656
H1 O4 3.4066 no . 2_666
H1 O6 2.7814 no . 2_656
H1 C9 3.3537 no . 2_656
H1 C14 3.4411 no . 2_666
H1 H4 2.7224 no . 2_666
H1 H12 3.2585 no . 2_656
H2 C7 3.5566 no . 2_666
H2 C8 3.5884 no . 2_656
H2 C12 3.3998 no . 2_656
H2 C13 3.5742 no . 1_655
H2 C13 3.5555 no . 2_656
H2 C19 3.1724 no . 1_655
H2 H3 2.8049 no . 1_655
H2 H4 2.8604 no . 2_666
H2 H8 2.7832 no . 1_655
H2 H10 2.7615 no . 1_655
H2 H10 3.5581 no . 2_656
H3 O5 2.5513 no . 1_455
H3 C11 3.5748 no . 1_455
H3 C16 3.4421 no . 1_455
H3 C19 3.5737 no . 2_556
H3 H2 2.8049 no . 1_455
H3 H10 2.6691 no . 2_556
H4 O5 3.4571 no . 1_455
H4 O6 2.4687 no . 1_565
H4 C8 2.8797 no . 2_666
H4 C11 2.9536 no . 2_666
H4 H1 2.7224 no . 2_666
H4 H2 2.8604 no . 2_666
H4 H8 3.2592 no . 2_566
H5 S1 3.5086 no . 2_657
H5 O6 2.8601 no . 2_657
H5 C18 3.2573 no . 2_667
H5 C20 3.4822 no . 2_667
H5 H6 3.2921 no . 2_667
H5 H7 2.4419 no . 2_667
H5 H11 3.1131 no . 2_667
H6 O5 2.4181 no . 1_455
H6 C16 3.5081 no . 1_455
H6 C19 3.5574 no . 2_556
H6 H5 3.2921 no . 2_667
H6 H9 3.2648 no . 2_556
H6 H10 2.9784 no . 2_556
H6 H15 3.0920 no . 2_667
H7 O6 3.2057 no . 1_565
H7 C17 3.3544 no . 2_667
H7 H5 2.4419 no . 2_667
H7 H14 3.2429 no . 2_767
H7 H15 3.4147 no . 2_667
H8 S1 3.4718 no . 2_556
H8 O2 3.5634 no . 2_556
H8 O3 3.3758 no . 2_556
H8 O4 3.5589 no . 2_666
H8 O5 2.7547 no . 2_666
H8 O6 3.1182 no . 2_556
H8 C16 3.2055 no . 2_666
H8 H2 2.7832 no . 1_455
H8 H4 3.2592 no . 2_566
H9 S1 3.4489 no . 2_556
H9 O2 3.5591 no . 2_556
H9 O3 2.7788 no . 2_556
H9 O5 3.4049 no . 2_656
H9 H6 3.2648 no . 2_556
H9 H12 2.8907 no . 2_656
H9 H16 3.4330 no . 1_454
H10 S1 3.5788 no . 2_556
H10 O2 3.0533 no . 2_556
H10 O3 3.4640 no . 2_556
H10 O5 3.2228 no . 2_656
H10 C13 3.0328 no . 2_556
H10 C18 3.4647 no . 2_556
H10 H2 2.7615 no . 1_455
H10 H2 3.5581 no . 2_656
H10 H3 2.6691 no . 2_556
H10 H6 2.9784 no . 2_556
H10 H10 3.4187 no . 2_556
H11 C17 3.3735 no . 2_667
H11 C22 3.4450 no . 1_455
H11 H5 3.1131 no . 2_667
H11 H13 2.5496 no . 1_455
H11 H14 3.3679 no . 1_455
H12 O3 2.9464 no . 1_655
H12 C23 3.4417 no . 2_757
H12 H1 3.2585 no . 2_656
H12 H9 2.8907 no . 2_656
H12 H14 3.4776 no . 2_767
H12 H16 2.4949 no . 2_757
H13 O3 2.5900 no . 1_655
H13 C15 3.4419 no . 2_757
H13 C20 3.4449 no . 1_655
H13 C22 3.1275 no . 2_757
H13 H11 2.5496 no . 1_655
H13 H13 3.1038 no . 2_757
H13 H14 3.2400 no . 2_767
H13 H16 3.1999 no . 2_757
H14 O4 3.1529 no . 2_767
H14 C10 3.3843 no . 2_767
H14 C15 3.0897 no . 2_767
H14 C17 3.3757 no . 2_767
H14 C20 3.5273 no . 2_767
H14 C21 3.0695 no . 2_767
H14 C22 2.9038 no . 2_767
H14 H7 3.2429 no . 2_767
H14 H11 3.3679 no . 1_655
H14 H12 3.4776 no . 2_767
H14 H13 3.2400 no . 2_767
H15 O4 2.9180 no . 2_767
H15 O5 3.0966 no . 2_767
H15 C16 3.4195 no . 2_767
H15 H6 3.0920 no . 2_667
H15 H7 3.4147 no . 2_667
H16 O3 3.1867 no . 2_657
H16 O4 3.1533 no . 2_767
H16 C21 2.9240 no . 2_757
H16 C22 3.3224 no . 2_757
H16 H9 3.4330 no . 1_656
H16 H12 2.4949 no . 2_757
H16 H13 3.1999 no . 2_757

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_613
_database_code_depnum_ccdc_archive 'CCDC 2044378'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2019-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F O5 S'
_chemical_formula_sum            'C16 H13 F O5 S'
_chemical_formula_weight         336.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H13 F1 O5 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   15.6045(4)
_cell_length_b                   5.62357(12)
_cell_length_c                   17.4711(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.938(2)
_cell_angle_gamma                90
_cell_volume                     1481.33(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4224
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.7800
_cell_measurement_theta_min      4.3780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.278
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (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    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10781
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.085
_diffrn_reflns_theta_min         3.390
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00 118.00   0.50    0.05    --   42.80  -4.00 -12.00  308
  2  ω    121.00 149.00   0.50    0.15    --   76.50   4.00 164.00   56
  3  ω      2.00  33.00   0.50    0.15    --   76.50 -57.00 -60.00   62
  4  ω    -44.00 -19.00   0.50    0.05    --  -42.80  -4.00 -12.00   50
  5  ω    -63.00  14.00   0.50    0.05    --  -42.80  57.00-120.00  154
  6  ω    -69.00 -43.00   0.50    0.15    -- -106.00  -4.00 -12.00   52
  7  ω    -82.00 -32.00   0.50    0.15    -- -106.00  57.00 -60.00  100
  8  ω    -81.00 -32.00   0.50    0.15    -- -106.00  77.00  30.00   98
  9  ω    -74.00 -44.00   0.50    0.15    -- -106.00 125.00  90.00   60
 10  ω   -109.00 -84.00   0.50    0.15    -- -106.00 125.00  90.00   50
 11  ω   -128.00-102.00   0.50    0.15    -- -106.00  77.00  30.00   52
 12  ω   -134.00 -41.00   0.50    0.15    -- -106.00  77.00 -30.00  186
 13  ω   -113.00 -72.00   0.50    0.05    --  -42.80  -4.00 -12.00   82
 14  ω   -134.00 -87.00   0.50    0.15    -- -106.00  -4.00 -12.00   94
 15  ω   -127.00 -30.00   0.50    0.15    -- -106.00  37.00 -60.00  194
 16  ω    -95.00 -69.00   0.50    0.15    -- -106.00 125.00-180.00   52
 17  ω   -129.00 -64.00   0.50    0.15    -- -106.00  77.00 -90.00  130
 18  ω   -169.00-144.00   0.50    0.15    -- -106.00  -4.00 -12.00   50
 19  ω   -157.00-118.00   0.50    0.15    -- -106.00 -57.00  90.00   78
 20  ω   -108.00 -83.00   0.50    0.15    -- -106.00 -57.00  90.00   50
 21  ω   -126.00-101.00   0.50    0.15    -- -106.00   4.00 164.00   50
 22  ω   -124.00 -75.00   0.50    0.15    -- -106.00 -19.00 120.00   98
 23  ω   -177.00 -84.00   0.50    0.15    -- -106.00 -37.00 150.00  186
 24  ω   -176.00-145.00   0.50    0.15    -- -106.00 -19.00 120.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0041428000
_diffrn_orient_matrix_UB_12      -0.0036212000
_diffrn_orient_matrix_UB_13      -0.0871452000
_diffrn_orient_matrix_UB_21      -0.1019474000
_diffrn_orient_matrix_UB_22      -0.0146155000
_diffrn_orient_matrix_UB_23      -0.0270075000
_diffrn_orient_matrix_UB_31      -0.0053949000
_diffrn_orient_matrix_UB_32      0.2735383000
_diffrn_orient_matrix_UB_33      -0.0025590000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2633
_reflns_number_total             2957
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1246
_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:
 C9AA(H9AA)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C4AA(H4AA), C6AA(H6AA), C0BA(H0BA), C2BA(H2BA), C3BA(H3BA),
 C4BA(H4BA)
2.d Idealised Me refined as rotating group:
 C(HA,HB,HC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S0AA S 0.42967(2) 0.12584(6) 0.64691(2) 0.02301(16) Uani 1 1 d . . . . .
O4 O 0.19426(7) 0.2955(2) 0.68043(6) 0.0246(3) Uani 1 1 d . . . . .
F0AA F 0.13197(8) 0.8206(2) 0.37928(6) 0.0400(3) Uani 1 1 d . . . . .
O0AA O 0.34501(7) 0.2894(2) 0.61693(6) 0.0239(3) Uani 1 1 d . . . . .
O1AA O 0.41771(9) -0.0547(2) 0.58745(7) 0.0309(3) Uani 1 1 d . . . . .
O2AA O 0.43718(9) 0.0613(2) 0.72746(7) 0.0310(3) Uani 1 1 d . . . . .
O3AA O 0.09384(8) 0.0125(2) 0.63149(7) 0.0326(3) Uani 1 1 d . . . . .
C1AA C 0.61745(12) 0.4596(3) 0.56945(10) 0.0308(4) Uani 1 1 d . . . . .
H1AA H 0.640634 0.453439 0.524266 0.037 Uiso 1 1 calc R . . . .
C2AA C 0.51845(10) 0.3109(3) 0.64216(9) 0.0236(3) Uani 1 1 d . . . . .
C3AA C 0.18092(10) 0.5245(3) 0.56713(9) 0.0234(3) Uani 1 1 d . . . . .
C4AA C 0.55049(11) 0.3045(3) 0.57480(10) 0.0281(3) Uani 1 1 d . . . . .
H4AA H 0.526737 0.195438 0.533226 0.034 Uiso 1 1 calc R . . . .
C5AA C 0.13031(12) 0.6584(3) 0.43619(10) 0.0286(4) Uani 1 1 d . . . . .
C6AA C 0.55281(11) 0.4695(3) 0.70356(9) 0.0296(4) Uani 1 1 d . . . . .
H6AA H 0.531416 0.470391 0.749780 0.036 Uiso 1 1 calc R . . . .
C7AA C 0.12380(10) 0.3338(3) 0.54830(9) 0.0230(3) Uani 1 1 d . . . . .
C8AA C 0.65157(11) 0.6245(3) 0.62880(10) 0.0296(4) Uani 1 1 d . . . . .
C9AA C 0.23019(10) 0.5079(3) 0.65313(9) 0.0235(3) Uani 1 1 d . . . . .
H9AA H 0.216418 0.649953 0.682296 0.028 Uiso 1 1 calc R . . . .
C0BA C 0.07231(11) 0.4674(3) 0.41524(9) 0.0285(4) Uani 1 1 d . . . . .
H0BA H 0.035946 0.452003 0.362739 0.034 Uiso 1 1 calc R . . . .
C C 0.72195(13) 0.7997(4) 0.62081(13) 0.0413(5) Uani 1 1 d . . . . .
HA H 0.776881 0.767489 0.661592 0.062 Uiso 1 1 calc GR . . . .
HB H 0.701814 0.961691 0.627388 0.062 Uiso 1 1 calc GR . . . .
HC H 0.732865 0.783732 0.568271 0.062 Uiso 1 1 calc GR . . . .
C1BA C 0.13161(10) 0.1914(3) 0.62062(9) 0.0241(3) Uani 1 1 d . . . . .
C2BA C 0.61887(12) 0.6263(3) 0.69612(11) 0.0324(4) Uani 1 1 d . . . . .
H2BA H 0.642207 0.736649 0.737413 0.039 Uiso 1 1 calc R . . . .
C3BA C 0.06871(10) 0.3006(3) 0.47232(9) 0.0261(3) Uani 1 1 d . . . . .
H3BA H 0.030016 0.167612 0.460281 0.031 Uiso 1 1 calc R . . . .
C4BA C 0.18622(11) 0.6942(3) 0.51057(10) 0.0271(3) Uani 1 1 d . . . . .
H4BA H 0.225622 0.825808 0.522341 0.033 Uiso 1 1 calc R . . . .
C1 C 0.32977(11) 0.4796(3) 0.66866(9) 0.0246(3) Uani 1 1 d . . . . .
H1A H 0.356954 0.629582 0.656783 0.030 Uiso 1 1 calc R . . . .
H1B H 0.356163 0.437817 0.724851 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S0AA O0AA 1.5838(11) . ?
S0AA O1AA 1.4300(12) . ?
S0AA O2AA 1.4287(12) . ?
S0AA C2AA 1.7515(16) . ?
O4 C9AA 1.4513(19) . ?
O4 C1BA 1.3651(19) . ?
F0AA C5AA 1.3544(19) . ?
O0AA C1 1.4589(18) . ?
O3AA C1BA 1.206(2) . ?
C1AA C4AA 1.383(2) . ?
C1AA C8AA 1.391(3) . ?
C2AA C4AA 1.393(2) . ?
C2AA C6AA 1.392(2) . ?
C3AA C7AA 1.379(2) . ?
C3AA C9AA 1.504(2) . ?
C3AA C4BA 1.392(2) . ?
C5AA C0BA 1.392(3) . ?
C5AA C4BA 1.381(2) . ?
C6AA C2BA 1.388(2) . ?
C7AA C1BA 1.474(2) . ?
C7AA C3BA 1.396(2) . ?
C8AA C 1.508(2) . ?
C8AA C2BA 1.398(2) . ?
C9AA C1 1.515(2) . ?
C0BA C3BA 1.381(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
O0AA S0AA C2AA 104.00(7) . . ?
O1AA S0AA O0AA 103.32(7) . . ?
O1AA S0AA C2AA 110.13(7) . . ?
O2AA S0AA O0AA 108.84(7) . . ?
O2AA S0AA O1AA 119.83(7) . . ?
O2AA S0AA C2AA 109.42(8) . . ?
C1BA O4 C9AA 111.25(11) . . ?
C1 O0AA S0AA 118.44(9) . . ?
C4AA C1AA C8AA 121.40(15) . . ?
C4AA C2AA S0AA 119.03(12) . . ?
C6AA C2AA S0AA 119.77(12) . . ?
C6AA C2AA C4AA 121.11(15) . . ?
C7AA C3AA C9AA 108.83(13) . . ?
C7AA C3AA C4BA 121.14(15) . . ?
C4BA C3AA C9AA 130.03(15) . . ?
C1AA C4AA C2AA 118.89(15) . . ?
F0AA C5AA C0BA 117.46(15) . . ?
F0AA C5AA C4BA 117.76(16) . . ?
C4BA C5AA C0BA 124.79(15) . . ?
C2BA C6AA C2AA 118.88(15) . . ?
C3AA C7AA C1BA 108.21(13) . . ?
C3AA C7AA C3BA 122.20(15) . . ?
C3BA C7AA C1BA 129.57(15) . . ?
C1AA C8AA C 120.96(16) . . ?
C1AA C8AA C2BA 118.67(15) . . ?
C2BA C8AA C 120.36(16) . . ?
O4 C9AA C3AA 103.77(12) . . ?
O4 C9AA C1 108.64(12) . . ?
C3AA C9AA C1 114.95(13) . . ?
C3BA C0BA C5AA 118.64(15) . . ?
O4 C1BA C7AA 107.93(13) . . ?
O3AA C1BA O4 121.33(14) . . ?
O3AA C1BA C7AA 130.74(15) . . ?
C6AA C2BA C8AA 121.01(16) . . ?
C0BA C3BA C7AA 117.79(15) . . ?
C5AA C4BA C3AA 115.43(15) . . ?
O0AA C1 C9AA 106.84(12) . . ?

_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 1.547
_oxdiff_exptl_absorpt_empirical_full_min 0.575
####################################################################### 
# 
# 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_xcalibur_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2044391'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H13 N O7 S'
_chemical_formula_moiety         'C16 H13 N O7 S'
_chemical_formula_weight         363.34
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.71410(4)
_cell_length_b                   8.87131(5)
_cell_length_c                   13.74570(7)
_cell_angle_alpha                102.3397(5)
_cell_angle_beta                 90.4626(5)
_cell_angle_gamma                99.7363(5)
_cell_volume                     787.467(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    46591
_cell_measurement_theta_min      5.16
_cell_measurement_theta_max      74.15
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_colour            nONE
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376.00
_exptl_absorpt_coefficient_mu    2.216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            69031
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_theta_max         74.34
_diffrn_reflns_theta_min         3.295
_diffrn_reflns_theta_full        74.34
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3210
_reflns_number_gt                3166
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 2.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1674
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3166
_refine_ls_number_parameters     239
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[0.0069Fo² + 1.0000σ(Fo²)]/(4Fo²)'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.545
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.74778(4) 0.10596(3) 1.09291(2) 0.01784(14) Uani 1 2 d . . .
O2 O 0.79833(14) -0.04668(10) 1.08075(7) 0.0246(3) Uani 1 2 d . . .
O3 O 0.79136(12) 0.15279(10) 0.98991(6) 0.0185(2) Uani 1 2 d . . .
O4 O 0.54895(14) 0.12958(11) 1.12065(7) 0.0246(2) Uani 1 2 d . . .
O5 O 1.30700(14) 0.35343(11) 0.83216(8) 0.0280(3) Uani 1 2 d . . .
O6 O 1.00923(13) 0.38996(10) 0.89838(7) 0.0244(3) Uani 1 2 d . . .
O7 O 1.09454(19) -0.15889(14) 0.53067(9) 0.0401(3) Uani 1 2 d . . .
O8 O 0.7759(2) -0.24950(14) 0.50471(9) 0.0461(3) Uani 1 2 d . . .
N26 N 0.9174(2) -0.15625(14) 0.55093(9) 0.0309(3) Uani 1 2 d . . .
C10 C 1.03692(19) 0.07364(14) 0.68448(10) 0.0229(3) Uani 1 2 d . . .
C11 C 0.79602(18) 0.32464(14) 0.87826(10) 0.0216(3) Uani 1 2 d . . .
C12 C 1.2058(2) 0.45357(15) 1.31033(10) 0.0248(3) Uani 1 2 d . . .
C13 C 0.99002(19) 0.18543(14) 0.76303(10) 0.0202(3) Uani 1 2 d . . .
C14 C 0.70141(17) 0.28201(13) 0.97056(9) 0.0201(3) Uani 1 2 d . . .
C15 C 0.79338(19) 0.19079(14) 0.78997(10) 0.0201(3) Uani 1 2 d . . .
C16 C 1.1282(2) 0.25043(15) 1.15915(10) 0.0221(3) Uani 1 2 d . . .
C17 C 0.8580(2) 0.33517(16) 1.26048(10) 0.0247(3) Uani 1 2 d . . .
C18 C 1.0007(2) 0.44118(16) 1.32680(10) 0.0266(3) Uani 1 2 d . . .
C19 C 0.92477(19) 0.24085(13) 1.17709(9) 0.0189(3) Uani 1 2 d . . .
C20 C 1.2671(2) 0.35714(15) 1.22602(11) 0.0248(3) Uani 1 2 d . . .
C21 C 0.6314(2) 0.08259(16) 0.73836(10) 0.0258(3) Uani 1 2 d . . .
C22 C 1.12561(19) 0.31323(15) 0.83079(10) 0.0218(3) Uani 1 2 d . . .
C23 C 0.8755(2) -0.03408(14) 0.63458(10) 0.0248(3) Uani 1 2 d . . .
C24 C 1.3614(2) 0.56841(19) 1.38169(12) 0.0351(4) Uani 1 2 d . . .
C25 C 0.6746(2) -0.03138(15) 0.65991(11) 0.0260(3) Uani 1 2 d . . .
H1 H 1.16937 0.07073 0.66596 0.0278 Uiso 1 2 calc R . .
H2 H 0.72761 0.40331 0.8584 0.0269 Uiso 1 2 calc R . .
H3 H 0.55612 0.2484 0.96077 0.0234 Uiso 1 2 calc R . .
H4 H 0.73077 0.3689 1.02792 0.0241 Uiso 1 2 calc R . .
H5 H 1.17194 0.18657 1.10361 0.0259 Uiso 1 2 calc R . .
H6 H 0.72065 0.3277 1.27164 0.0285 Uiso 1 2 calc R . .
H7 H 0.95715 0.50416 1.38278 0.0307 Uiso 1 2 calc R . .
H8 H 1.40425 0.36478 1.21424 0.0301 Uiso 1 2 calc R . .
H9 H 0.49908 0.08749 0.75643 0.0308 Uiso 1 2 calc R . .
H10 H 1.43756 0.641 1.34735 0.0417 Uiso 1 2 calc R . .
H11 H 1.29371 0.62475 1.43517 0.0420 Uiso 1 2 calc R . .
H12 H 1.45125 0.51228 1.40827 0.0417 Uiso 1 2 calc R . .
H13 H 0.57088 -0.10539 0.6236 0.0295 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
S1 O2 1.4270(10) yes .
S1 O3 1.5747(9) yes .
S1 O4 1.4283(10) yes .
S1 C19 1.7573(11) yes .
O3 C14 1.4531(16) yes .
O5 C22 1.2086(15) yes .
O6 C11 1.4512(14) yes .
O6 C22 1.3632(16) yes .
O7 N26 1.2268(19) yes .
O8 N26 1.2209(16) yes .
N26 C23 1.4668(17) yes .
C10 C13 1.3791(17) yes .
C10 C23 1.3841(16) yes .
C11 C14 1.5143(19) yes .
C11 C15 1.5032(17) yes .
C12 C18 1.3868(19) yes .
C12 C20 1.3955(19) yes .
C12 C24 1.5125(18) yes .
C13 C15 1.3799(18) yes .
C13 C22 1.4723(16) yes .
C15 C21 1.3967(16) yes .
C16 C19 1.3817(19) yes .
C16 C20 1.3878(17) yes .
C17 C18 1.3956(17) yes .
C17 C19 1.3928(18) yes .
C21 C25 1.3811(19) yes .
C23 C25 1.399(2) yes .
C10 H1 0.930 no .
C11 H2 0.980 no .
C14 H3 0.970 no .
C14 H4 0.970 no .
C16 H5 0.930 no .
C17 H6 0.930 no .
C18 H7 0.930 no .
C20 H8 0.930 no .
C21 H9 0.930 no .
C24 H10 0.960 no .
C24 H11 0.960 no .
C24 H12 0.960 no .
C25 H13 0.930 no .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 S1 O3 104.80(5) yes . .
O2 S1 O4 119.49(6) yes . .
O2 S1 C19 109.35(6) yes . .
O3 S1 O4 109.39(6) yes . .
O3 S1 C19 103.92(5) yes . .
O4 S1 C19 108.75(6) yes . .
S1 O3 C14 116.64(7) yes . .
C11 O6 C22 111.33(9) yes . .
O7 N26 O8 123.18(12) yes . .
O7 N26 C23 117.85(11) yes . .
O8 N26 C23 118.97(13) yes . .
C13 C10 C23 116.19(12) yes . .
O6 C11 C14 110.56(10) yes . .
O6 C11 C15 103.93(10) yes . .
C14 C11 C15 115.79(10) yes . .
C18 C12 C20 118.59(11) yes . .
C18 C12 C24 121.27(12) yes . .
C20 C12 C24 120.14(12) yes . .
C10 C13 C15 122.04(11) yes . .
C10 C13 C22 129.32(12) yes . .
C15 C13 C22 108.64(11) yes . .
O3 C14 C11 106.65(9) yes . .
C11 C15 C13 108.38(10) yes . .
C11 C15 C21 130.34(12) yes . .
C13 C15 C21 121.28(11) yes . .
C19 C16 C20 118.68(12) yes . .
C18 C17 C19 118.90(12) yes . .
C12 C18 C17 120.93(12) yes . .
S1 C19 C16 119.02(9) yes . .
S1 C19 C17 119.65(10) yes . .
C16 C19 C17 121.33(10) yes . .
C12 C20 C16 121.57(12) yes . .
C15 C21 C25 117.78(12) yes . .
O5 C22 O6 121.75(11) yes . .
O5 C22 C13 130.57(12) yes . .
O6 C22 C13 107.67(10) yes . .
N26 C23 C10 118.36(12) yes . .
N26 C23 C25 118.56(11) yes . .
C10 C23 C25 123.08(12) yes . .
C21 C25 C23 119.61(11) yes . .
C13 C10 H1 121.992 no . .
C23 C10 H1 121.815 no . .
O6 C11 H2 108.692 no . .
C14 C11 H2 108.909 no . .
C15 C11 H2 108.696 no . .
O3 C14 H3 108.835 no . .
O3 C14 H4 108.630 no . .
C11 C14 H3 111.843 no . .
C11 C14 H4 111.391 no . .
H3 C14 H4 109.383 no . .
C19 C16 H5 120.944 no . .
C20 C16 H5 120.377 no . .
C18 C17 H6 120.616 no . .
C19 C17 H6 120.482 no . .
C12 C18 H7 119.765 no . .
C17 C18 H7 119.309 no . .
C12 C20 H8 119.226 no . .
C16 C20 H8 119.201 no . .
C15 C21 H9 120.879 no . .
C25 C21 H9 121.345 no . .
C12 C24 H10 109.860 no . .
C12 C24 H11 109.233 no . .
C12 C24 H12 109.410 no . .
H10 C24 H11 109.445 no . .
H10 C24 H12 109.439 no . .
H11 C24 H12 109.440 no . .
C21 C25 H13 120.356 no . .
C23 C25 H13 120.027 no . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O2 S1 O3 C14 163.20(5) no . . . .
O2 S1 C19 C16 54.32(11) no . . . .
O2 S1 C19 C17 -125.38(9) no . . . .
O4 S1 O3 C14 33.95(7) no . . . .
O3 S1 C19 C16 -57.15(10) no . . . .
O3 S1 C19 C17 123.15(9) no . . . .
C19 S1 O3 C14 -82.05(7) no . . . .
O4 S1 C19 C16 -173.60(9) no . . . .
O4 S1 C19 C17 6.70(11) no . . . .
S1 O3 C14 C11 169.36(5) no . . . .
C11 O6 C22 O5 177.14(12) no . . . .
C11 O6 C22 C13 -2.24(14) no . . . .
C22 O6 C11 C14 126.88(10) no . . . .
C22 O6 C11 C15 2.00(14) no . . . .
O7 N26 C23 C10 1.6(2) no . . . .
O7 N26 C23 C25 -178.73(12) no . . . .
O8 N26 C23 C10 -178.14(13) no . . . .
O8 N26 C23 C25 1.6(2) no . . . .
C13 C10 C23 N26 -179.52(12) no . . . .
C13 C10 C23 C25 0.8(2) no . . . .
C23 C10 C13 C15 -0.6(2) no . . . .
C23 C10 C13 C22 179.16(12) no . . . .
O6 C11 C14 O3 -67.15(10) no . . . .
O6 C11 C15 C13 -0.96(14) no . . . .
O6 C11 C15 C21 178.62(12) no . . . .
C14 C11 C15 C13 -122.41(11) no . . . .
C14 C11 C15 C21 57.16(19) no . . . .
C15 C11 C14 O3 50.69(13) no . . . .
C18 C12 C20 C16 0.0(2) no . . . .
C20 C12 C18 C17 -0.3(2) no . . . .
C24 C12 C18 C17 179.85(13) no . . . .
C24 C12 C20 C16 179.92(13) no . . . .
C10 C13 C15 C11 179.47(12) no . . . .
C10 C13 C15 C21 -0.2(2) no . . . .
C10 C13 C22 O5 2.5(3) no . . . .
C10 C13 C22 O6 -178.19(14) no . . . .
C15 C13 C22 O5 -177.74(14) no . . . .
C15 C13 C22 O6 1.56(16) no . . . .
C22 C13 C15 C11 -0.31(15) no . . . .
C22 C13 C15 C21 -179.93(11) no . . . .
C11 C15 C21 C25 -178.84(13) no . . . .
C13 C15 C21 C25 0.7(2) no . . . .
C19 C16 C20 C12 0.2(2) no . . . .
C20 C16 C19 S1 -179.94(11) no . . . .
C20 C16 C19 C17 -0.2(2) no . . . .
C18 C17 C19 S1 179.72(11) no . . . .
C18 C17 C19 C16 0.0(2) no . . . .
C19 C17 C18 C12 0.2(2) no . . . .
C15 C21 C25 C23 -0.5(2) no . . . .
N26 C23 C25 C21 -179.96(12) no . . . .
C10 C23 C25 C21 -0.3(2) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O2 C16 3.1285(14) no . .
O3 O6 2.8757(13) no . .
O3 C13 3.4513(16) no . .
O3 C15 2.8394(17) no . .
O3 C16 3.1094(15) no . .
O3 C21 3.5058(16) no . .
O3 C22 3.4894(16) no . .
O4 C14 2.8091(16) no . .
O4 C17 2.9129(15) no . .
O5 C10 3.1360(14) no . .
O5 C11 3.4706(15) no . .
O5 C15 3.4982(15) no . .
O7 C10 2.7007(17) no . .
O7 C25 3.5617(19) no . .
O8 C10 3.5495(15) no . .
O8 C25 2.7315(18) no . .
C10 C21 2.8369(19) no . .
C12 C19 2.7817(16) no . .
C13 C14 3.4975(18) no . .
C13 C25 2.7571(17) no . .
C14 C19 3.3168(18) no . .
C14 C21 3.2892(17) no . .
C14 C22 3.4538(18) no . .
C15 C23 2.7232(17) no . .
C16 C18 2.7860(18) no . .
C17 C20 2.7720(19) no . .
S1 O4 3.5817(9) no . 2_657
O2 O3 3.1541(13) no . 2_757
O2 O4 3.4766(13) no . 2_657
O2 O5 3.1771(14) no . 2_757
O2 O6 3.5671(14) no . 2_757
O2 C10 3.4723(17) no . 2_757
O2 C13 3.1333(18) no . 2_757
O2 C16 3.4878(16) no . 2_757
O2 C22 2.9930(18) no . 2_757
O3 O2 3.1541(13) no . 2_757
O3 O4 3.1916(11) no . 2_657
O4 S1 3.5817(9) no . 2_657
O4 O2 3.4766(13) no . 2_657
O4 O3 3.1916(11) no . 2_657
O4 O4 3.5936(12) no . 2_657
O4 C16 3.1961(17) no . 1_455
O4 C20 3.1371(17) no . 1_455
O4 C21 3.0970(18) no . 2_657
O4 C25 3.5867(18) no . 2_657
O5 O2 3.1771(14) no . 2_757
O5 C11 3.4009(16) no . 1_655
O5 C14 3.4691(16) no . 1_655
O5 C21 3.5596(17) no . 1_655
O6 O2 3.5671(14) no . 2_757
O6 O6 3.0640(12) no . 2_767
O6 C14 3.3584(13) no . 2_767
O7 O7 3.533(2) no . 2_756
O7 N26 3.2396(19) no . 2_756
O7 C10 3.352(2) no . 2_756
O7 C17 3.586(2) no . 2_757
O7 C18 3.478(2) no . 2_757
O7 C23 3.112(2) no . 2_756
O7 C24 3.559(2) no . 1_544
O8 C10 3.4497(19) no . 2_756
O8 C12 3.434(2) no . 2_757
O8 C24 3.2326(19) no . 1_444
O8 C24 3.510(2) no . 2_757
N26 O7 3.2396(19) no . 2_756
N26 N26 3.3942(19) no . 2_756
N26 C10 3.4721(19) no . 2_756
N26 C12 3.566(2) no . 2_757
N26 C18 3.433(2) no . 2_757
N26 C23 3.5200(19) no . 2_756
C10 O2 3.4723(17) no . 2_757
C10 O7 3.352(2) no . 2_756
C10 O8 3.4497(19) no . 2_756
C10 N26 3.4721(19) no . 2_756
C11 O5 3.4009(16) no . 1_455
C11 C12 3.575(2) no . 2_767
C11 C20 3.511(2) no . 2_767
C12 O8 3.434(2) no . 2_757
C12 N26 3.566(2) no . 2_757
C12 C11 3.575(2) no . 2_767
C13 O2 3.1333(18) no . 2_757
C14 O5 3.4691(16) no . 1_455
C14 O6 3.3584(13) no . 2_767
C16 O2 3.4878(16) no . 2_757
C16 O4 3.1961(17) no . 1_655
C17 O7 3.586(2) no . 2_757
C17 C22 3.588(2) no . 2_767
C18 O7 3.478(2) no . 2_757
C18 N26 3.433(2) no . 2_757
C18 C22 3.574(2) no . 2_767
C20 O4 3.1371(17) no . 1_655
C20 C11 3.511(2) no . 2_767
C21 O4 3.0970(18) no . 2_657
C21 O5 3.5596(17) no . 1_455
C22 O2 2.9930(18) no . 2_757
C22 C17 3.588(2) no . 2_767
C22 C18 3.574(2) no . 2_767
C23 O7 3.112(2) no . 2_756
C23 N26 3.5200(19) no . 2_756
C24 O7 3.559(2) no . 1_566
C24 O8 3.2326(19) no . 1_666
C24 O8 3.510(2) no . 2_757
C25 O4 3.5867(18) no . 2_657
S1 H3 2.8364 no . .
S1 H4 2.6891 no . .
S1 H5 2.8112 no . .
S1 H6 2.8287 no . .
O2 H5 2.9371 no . .
O3 H2 3.2275 no . .
O3 H5 2.9220 no . .
O4 H3 2.6302 no . .
O4 H4 2.8156 no . .
O4 H6 2.5382 no . .
O5 H1 3.0159 no . .
O6 H3 3.2830 no . .
O6 H4 2.6036 no . .
O7 H1 2.4248 no . .
O8 H13 2.4367 no . .
N26 H1 2.6194 no . .
N26 H13 2.6102 no . .
C10 H13 3.2745 no . .
C11 H9 2.8683 no . .
C12 H5 3.2661 no . .
C12 H6 3.2599 no . .
C13 H2 2.9436 no . .
C13 H9 3.2590 no . .
C14 H9 3.2339 no . .
C15 H1 3.2582 no . .
C15 H3 2.8520 no . .
C15 H4 3.3778 no . .
C15 H13 3.2271 no . .
C16 H6 3.2556 no . .
C17 H4 3.3897 no . .
C17 H5 3.2599 no . .
C18 H8 3.2302 no . .
C18 H10 3.1367 no . .
C18 H11 2.5638 no . .
C18 H12 3.1305 no . .
C19 H4 2.9401 no . .
C19 H7 3.2393 no . .
C19 H8 3.2202 no . .
C20 H7 3.2348 no . .
C20 H10 2.7626 no . .
C20 H11 3.2961 no . .
C20 H12 2.7567 no . .
C21 H2 2.9308 no . .
C21 H3 3.1812 no . .
C22 H1 2.8265 no . .
C22 H2 2.9210 no . .
C23 H9 3.2518 no . .
C24 H7 2.6780 no . .
C24 H8 2.6559 no . .
C25 H1 3.2875 no . .
H2 H3 2.3477 no . .
H2 H4 2.4143 no . .
H2 H9 3.0002 no . .
H3 H9 2.8562 no . .
H4 H6 3.4467 no . .
H5 H8 2.3119 no . .
H6 H7 2.3246 no . .
H7 H10 3.3269 no . .
H7 H11 2.3656 no . .
H7 H12 3.3201 no . .
H8 H10 2.7008 no . .
H8 H11 3.5657 no . .
H8 H12 2.6982 no . .
H9 H13 2.3349 no . .
S1 H3 3.3771 no . 2_657
S1 H5 3.4384 no . 2_757
S1 H9 3.2548 no . 2_657
O2 H1 3.5405 no . 2_757
O2 H3 2.7005 no . 2_657
O2 H5 2.5980 no . 2_757
O2 H9 3.0498 no . 2_657
O3 H5 3.0625 no . 2_757
O4 H3 3.2523 no . 2_657
O4 H5 2.6817 no . 1_455
O4 H8 2.5517 no . 1_455
O4 H9 2.8030 no . 2_657
O5 H2 2.7917 no . 1_655
O5 H3 2.8239 no . 1_655
O5 H4 2.8329 no . 2_767
O5 H6 3.4599 no . 2_767
O5 H8 3.0784 no . 2_867
O5 H9 2.8834 no . 1_655
O5 H10 3.0206 no . 2_867
O6 H4 2.5361 no . 2_767
O7 H1 3.5145 no . 2_756
O7 H7 3.2185 no . 1_544
O7 H7 3.4817 no . 2_757
O7 H11 2.6486 no . 1_544
O7 H13 3.3536 no . 1_655
O8 H1 3.0921 no . 2_756
O8 H7 2.9041 no . 1_544
O8 H10 3.0096 no . 1_444
O8 H11 3.3030 no . 1_444
O8 H11 3.5552 no . 2_757
O8 H12 2.8586 no . 1_444
O8 H12 3.0347 no . 2_757
N26 H1 3.3002 no . 2_756
N26 H7 3.4344 no . 1_544
C10 H9 3.2236 no . 1_655
C11 H10 3.5576 no . 2_767
C12 H2 2.8766 no . 2_767
C15 H10 3.1833 no . 2_767
C16 H2 3.1218 no . 2_767
C17 H8 3.1729 no . 1_455
C18 H2 3.5264 no . 2_767
C20 H2 2.6255 no . 2_767
C20 H6 3.1691 no . 1_655
C21 H1 3.2280 no . 1_455
C21 H10 3.0373 no . 2_767
C22 H3 3.5771 no . 1_655
C22 H4 3.0599 no . 2_767
C22 H9 3.4940 no . 1_655
C24 H2 3.4182 no . 2_767
C24 H12 3.4000 no . 2_868
H1 O2 3.5405 no . 2_757
H1 O7 3.5145 no . 2_756
H1 O8 3.0921 no . 2_756
H1 N26 3.3002 no . 2_756
H1 C21 3.2280 no . 1_655
H1 H9 2.4969 no . 1_655
H1 H10 3.3858 no . 2_867
H1 H13 3.3329 no . 1_655
H2 O5 2.7917 no . 1_455
H2 C12 2.8766 no . 2_767
H2 C16 3.1218 no . 2_767
H2 C18 3.5264 no . 2_767
H2 C20 2.6255 no . 2_767
H2 C24 3.4182 no . 2_767
H2 H5 3.5096 no . 2_767
H2 H8 2.7374 no . 2_767
H2 H10 2.9512 no . 2_767
H3 S1 3.3771 no . 2_657
H3 O2 2.7005 no . 2_657
H3 O4 3.2523 no . 2_657
H3 O5 2.8239 no . 1_455
H3 C22 3.5771 no . 1_455
H3 H5 3.2974 no . 1_455
H4 O5 2.8329 no . 2_767
H4 O6 2.5361 no . 2_767
H4 C22 3.0599 no . 2_767
H4 H8 3.3868 no . 1_455
H5 S1 3.4384 no . 2_757
H5 O2 2.5980 no . 2_757
H5 O3 3.0625 no . 2_757
H5 O4 2.6817 no . 1_655
H5 H2 3.5096 no . 2_767
H5 H3 3.2974 no . 1_655
H6 O5 3.4599 no . 2_767
H6 C20 3.1691 no . 1_455
H6 H8 2.3588 no . 1_455
H6 H12 3.0368 no . 1_455
H6 H13 3.1222 no . 2_657
H7 O7 3.2185 no . 1_566
H7 O7 3.4817 no . 2_757
H7 O8 2.9041 no . 1_566
H7 N26 3.4344 no . 1_566
H7 H7 3.2875 no . 2_768
H7 H11 3.3236 no . 2_768
H7 H12 3.4288 no . 1_455
H8 O4 2.5517 no . 1_655
H8 O5 3.0784 no . 2_867
H8 C17 3.1729 no . 1_655
H8 H2 2.7374 no . 2_767
H8 H4 3.3868 no . 1_655
H8 H6 2.3588 no . 1_655
H8 H13 3.5507 no . 2_757
H9 S1 3.2548 no . 2_657
H9 O2 3.0498 no . 2_657
H9 O4 2.8030 no . 2_657
H9 O5 2.8834 no . 1_455
H9 C10 3.2236 no . 1_455
H9 C22 3.4940 no . 1_455
H9 H1 2.4969 no . 1_455
H9 H10 3.0248 no . 2_767
H10 O5 3.0206 no . 2_867
H10 O8 3.0096 no . 1_666
H10 C11 3.5576 no . 2_767
H10 C15 3.1833 no . 2_767
H10 C21 3.0373 no . 2_767
H10 H1 3.3858 no . 2_867
H10 H2 2.9512 no . 2_767
H10 H9 3.0248 no . 2_767
H11 O7 2.6486 no . 1_566
H11 O8 3.3030 no . 1_666
H11 O8 3.5552 no . 2_757
H11 H7 3.3236 no . 2_768
H11 H12 3.2869 no . 2_868
H11 H13 3.4159 no . 1_666
H12 O8 2.8586 no . 1_666
H12 O8 3.0347 no . 2_757
H12 C24 3.4000 no . 2_868
H12 H6 3.0368 no . 1_655
H12 H7 3.4288 no . 1_655
H12 H11 3.2869 no . 2_868
H12 H12 2.6631 no . 2_868
H12 H13 3.5193 no . 2_757
H13 O7 3.3536 no . 1_455
H13 H1 3.3329 no . 1_455
H13 H6 3.1222 no . 2_657
H13 H8 3.5507 no . 2_757
H13 H11 3.4159 no . 1_444
H13 H12 3.5193 no . 2_757

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_643
_database_code_depnum_ccdc_archive 'CCDC 2044390'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 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     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 O5 S'
_chemical_formula_sum            'C17 H16 O5 S'
_chemical_formula_weight         332.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H13 F3 O5 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.1303(4)
_cell_length_b                   7.39046(10)
_cell_length_c                   16.1869(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.3621(15)
_cell_angle_gamma                90
_cell_volume                     3157.71(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8178
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.7280
_cell_measurement_theta_min      5.6380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (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_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14773
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.238
_diffrn_reflns_theta_min         3.349
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  58.00   0.50    0.88    --   42.80 -71.00  93.00   78
  2  ω     28.00  53.00   0.50    2.17    --   76.50 -71.00  93.00   50
  3  ω     68.00  94.00   0.50    0.88    --   42.80  71.00-135.00   52
  4  ω     71.00  96.00   0.50    0.88    --   42.80 125.00-180.00   50
  5  ω     73.00 117.00   0.50    0.88    --   42.80 125.00-150.00   88
  6  ω     72.00 117.00   0.50    0.88    --   42.80 125.00 -30.00   90
  7  ω     71.00 108.00   0.50    0.88    --   42.80 125.00  90.00   74
  8  ω     79.00 110.00   0.50    0.88    --   42.80 125.00 150.00   62
  9  ω    -55.00 -29.00   0.50    2.17    -- -106.00  37.00-120.00   52
 10  ω    -79.00 -35.00   0.50    2.17    -- -106.00  71.00-135.00   88
 11  ω    -61.00   3.00   0.50    0.88    --  -42.80  71.00-135.00  128
 12  ω    -65.00 -39.00   0.50    2.17    -- -106.00  57.00   0.00   52
 13  ω    -86.00 -34.00   0.50    2.17    -- -106.00  37.00  90.00  104
 14  ω    -99.00 -56.00   0.50    2.17    -- -106.00 125.00 150.00   86
 15  ω   -101.00 -75.00   0.50    2.17    -- -106.00  37.00  60.00   52
 16  ω   -119.00 -91.00   0.50    2.17    -- -106.00  57.00   0.00   56
 17  ω   -116.00 -90.00   0.50    2.17    -- -106.00 125.00  60.00   52
 18  ω   -117.00 -45.00   0.50    2.17    -- -106.00 125.00 -30.00  144
 19  ω   -122.00 -97.00   0.50    2.17    -- -106.00  71.00-135.00   50
 20  ω   -128.00 -72.00   0.50    2.17    -- -106.00  37.00-120.00  112
 21  ω    -98.00 -60.00   0.50    2.17    -- -106.00  58.00-174.41   76
 22  ω   -172.00-146.00   0.50    2.17    -- -106.00 -57.00-180.00   52
 23  ω   -175.00-148.00   0.50    2.17    -- -106.00 -37.00-120.00   54
 24  ω   -175.00 -91.00   0.50    2.17    -- -106.00 -57.00-150.00  168
 25  ω   -139.00-113.00   0.50    2.17    -- -106.00 -99.00-150.00   52
 26  ω   -165.00-129.00   0.50    2.17    -- -106.00 -99.00 -30.00   72
 27  ω   -175.00-115.00   0.50    2.17    -- -106.00-125.00  60.00  120
 28  ω    -96.00 -71.00   0.50    2.17    -- -106.00-125.00  60.00   50
 29  ω   -114.00 -89.00   0.50    2.17    -- -106.00 -77.00 120.00   50
 30  ω   -128.00-103.00   0.50    2.17    -- -106.00 -71.00  93.00   50
 31  ω   -137.00-111.00   0.50    2.17    -- -106.00 -37.00  60.00   52
 32  ω   -155.00-129.00   0.50    2.17    -- -106.00 -77.00  90.00   52
 33  ω   -135.00-110.00   0.50    2.17    -- -106.00 -37.00 150.00   50
 34  ω   -155.00-129.00   0.50    2.17    -- -106.00 -19.00 150.00   52
 35  ω   -173.00-120.00   0.50    2.17    -- -106.00 -77.00 120.00  106
 36  ω   -174.00-110.00   0.50    2.17    -- -106.00 -57.00  90.00  128
 37  ω   -108.00 -74.00   0.50    0.88    --  -42.80-125.00 150.00   68
 38  ω   -173.00-126.00   0.50    2.17    -- -106.00 -19.00 120.00   94
 39  ω   -174.00 -91.00   0.50    2.17    -- -106.00 -57.00 150.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0259941000
_diffrn_orient_matrix_UB_12      0.1552094000
_diffrn_orient_matrix_UB_13      -0.0373083000
_diffrn_orient_matrix_UB_21      -0.0270171000
_diffrn_orient_matrix_UB_22      -0.0593006000
_diffrn_orient_matrix_UB_23      -0.0903630000
_diffrn_orient_matrix_UB_31      -0.0447407000
_diffrn_orient_matrix_UB_32      0.1257834000
_diffrn_orient_matrix_UB_33      0.0034557000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2948
_reflns_number_total             3206
_reflns_odcompleteness_completeness 99.06
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.046
_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     210
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1221
_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:
 C2BA(H2BA)
2.b Secondary CH2 refined with riding coordinates:
 C(HA,HB)
2.c Aromatic/amide H refined with riding coordinates:
 C6AA(H6AA), C7AA(H7AA), C8AA(H8AA), C0BA(H0BA), C1BA(H1BA), C4BA(H4BA),
 C5BA(H5BA)
2.d Idealised Me refined as rotating group:
 C3BA(H3BA,H3BB,H3BC), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S0AA S 0.41678(2) 0.14864(4) 0.31355(2) 0.02420(15) Uani 1 1 d . . . . .
O O 0.27061(3) 0.38732(11) 0.19888(6) 0.0233(2) Uani 1 1 d . . . . .
O0AA O 0.28141(4) 0.65244(12) 0.13891(7) 0.0295(2) Uani 1 1 d . . . . .
O1AA O 0.45127(4) 0.29685(14) 0.32062(6) 0.0340(3) Uani 1 1 d . . . . .
O2AA O 0.41197(4) 0.05147(15) 0.38779(6) 0.0322(2) Uani 1 1 d . . . . .
O3AA O 0.36377(3) 0.23743(12) 0.27123(6) 0.0238(2) Uani 1 1 d . . . . .
C1AA C 0.30312(4) 0.36748(15) 0.07956(8) 0.0197(3) Uani 1 1 d . . . . .
C2AA C 0.28506(4) 0.49032(16) 0.13815(8) 0.0220(3) Uani 1 1 d . . . . .
C3AA C 0.42737(4) -0.00667(19) 0.23778(8) 0.0249(3) Uani 1 1 d . . . . .
C4AA C 0.29951(4) 0.19214(16) 0.10718(7) 0.0196(3) Uani 1 1 d . . . . .
C C 0.31830(5) 0.12854(16) 0.26433(8) 0.0219(3) Uani 1 1 d . . . . .
HA H 0.304886 0.142239 0.315904 0.026 Uiso 1 1 calc R . . . .
HB H 0.325860 -0.000898 0.257468 0.026 Uiso 1 1 calc R . . . .
C5AA C 0.32174(4) 0.40742(16) 0.00744(8) 0.0221(3) Uani 1 1 d . . . . .
C6AA C 0.33330(5) 0.08191(17) -0.00528(8) 0.0237(3) Uani 1 1 d . . . . .
H6AA H 0.344197 -0.015421 -0.035022 0.028 Uiso 1 1 calc R . . . .
C7AA C 0.33677(5) 0.25870(17) -0.03360(8) 0.0233(3) Uani 1 1 d . . . . .
H7AA H 0.349819 0.278324 -0.082503 0.028 Uiso 1 1 calc R . . . .
C8AA C 0.44186(5) 0.0577(2) 0.16593(8) 0.0298(3) Uani 1 1 d . . . . .
H8AA H 0.444495 0.183954 0.156870 0.036 Uiso 1 1 calc R . . . .
C9AA C 0.44872(6) -0.2518(2) 0.12053(10) 0.0395(4) Uani 1 1 d . . . . .
C0BA C 0.42287(6) -0.1902(2) 0.25100(9) 0.0361(3) Uani 1 1 d . . . . .
H0BA H 0.412648 -0.232437 0.299900 0.043 Uiso 1 1 calc R . . . .
C1BA C 0.31416(4) 0.04523(16) 0.06581(8) 0.0224(3) Uani 1 1 d . . . . .
H1BA H 0.311316 -0.075050 0.084884 0.027 Uiso 1 1 calc R . . . .
C2BA C 0.28019(4) 0.19677(15) 0.18705(7) 0.0204(3) Uani 1 1 d . . . . .
H2BA H 0.247956 0.126326 0.178989 0.025 Uiso 1 1 calc R . . . .
C3BA C 0.32503(5) 0.59723(18) -0.02402(9) 0.0285(3) Uani 1 1 d . . . . .
H3BA H 0.291046 0.650491 -0.039086 0.043 Uiso 1 1 calc GR . . . .
H3BB H 0.339475 0.595232 -0.074190 0.043 Uiso 1 1 calc GR . . . .
H3BC H 0.346703 0.669813 0.020675 0.043 Uiso 1 1 calc GR . . . .
C4BA C 0.45232(5) -0.0660(2) 0.10804(9) 0.0346(3) Uani 1 1 d . . . . .
H4BA H 0.462140 -0.023407 0.058837 0.042 Uiso 1 1 calc R . . . .
C5BA C 0.43342(7) -0.3119(2) 0.19226(11) 0.0457(4) Uani 1 1 d . . . . .
H5BA H 0.430178 -0.438043 0.201031 0.055 Uiso 1 1 calc R . . . .
C1 C 0.46307(8) -0.3855(3) 0.05985(12) 0.0564(5) Uani 1 1 d . . . . .
H1A H 0.462506 -0.325384 0.005674 0.085 Uiso 1 1 calc GR . . . .
H1B H 0.438850 -0.485995 0.050445 0.085 Uiso 1 1 calc GR . . . .
H1C H 0.497183 -0.432045 0.083954 0.085 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
S0AA O1AA 1.4278(10) . ?
S0AA O2AA 1.4316(10) . ?
S0AA O3AA 1.5852(9) . ?
S0AA C3AA 1.7514(13) . ?
O C2AA 1.3702(15) . ?
O C2BA 1.4527(14) . ?
O0AA C2AA 1.2026(16) . ?
O3AA C 1.4554(14) . ?
C1AA C2AA 1.4759(16) . ?
C1AA C4AA 1.3816(16) . ?
C1AA C5AA 1.4063(16) . ?
C3AA C8AA 1.3944(17) . ?
C3AA C0BA 1.383(2) . ?
C4AA C1BA 1.3814(17) . ?
C4AA C2BA 1.5035(16) . ?
C C2BA 1.5133(16) . ?
C5AA C7AA 1.3932(17) . ?
C5AA C3BA 1.5020(16) . ?
C6AA C7AA 1.3950(18) . ?
C6AA C1BA 1.3941(17) . ?
C8AA C4BA 1.384(2) . ?
C9AA C4BA 1.395(3) . ?
C9AA C5BA 1.393(2) . ?
C9AA C1 1.506(2) . ?
C0BA C5BA 1.386(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
O1AA S0AA O2AA 120.18(6) . . ?
O1AA S0AA O3AA 103.26(6) . . ?
O1AA S0AA C3AA 110.39(6) . . ?
O2AA S0AA O3AA 108.71(5) . . ?
O2AA S0AA C3AA 108.71(6) . . ?
O3AA S0AA C3AA 104.36(5) . . ?
C2AA O C2BA 110.75(9) . . ?
C O3AA S0AA 118.20(7) . . ?
C4AA C1AA C2AA 108.06(10) . . ?
C4AA C1AA C5AA 122.10(11) . . ?
C5AA C1AA C2AA 129.83(11) . . ?
O C2AA C1AA 108.17(10) . . ?
O0AA C2AA O 120.55(11) . . ?
O0AA C2AA C1AA 131.28(12) . . ?
C8AA C3AA S0AA 118.96(11) . . ?
C0BA C3AA S0AA 119.98(10) . . ?
C0BA C3AA C8AA 121.03(12) . . ?
C1AA C4AA C1BA 122.03(11) . . ?
C1AA C4AA C2BA 108.77(10) . . ?
C1BA C4AA C2BA 129.14(11) . . ?
O3AA C C2BA 106.52(9) . . ?
C1AA C5AA C3BA 122.57(11) . . ?
C7AA C5AA C1AA 115.54(11) . . ?
C7AA C5AA C3BA 121.89(11) . . ?
C1BA C6AA C7AA 121.31(11) . . ?
C5AA C7AA C6AA 122.19(12) . . ?
C4BA C8AA C3AA 118.74(14) . . ?
C4BA C9AA C1 120.93(16) . . ?
C5BA C9AA C4BA 118.63(13) . . ?
C5BA C9AA C1 120.40(17) . . ?
C3AA C0BA C5BA 119.39(14) . . ?
C4AA C1BA C6AA 116.81(11) . . ?
O C2BA C4AA 104.12(9) . . ?
O C2BA C 108.84(9) . . ?
C4AA C2BA C 113.32(10) . . ?
C8AA C4BA C9AA 121.31(13) . . ?
C0BA C5BA C9AA 120.88(16) . . ?

_olex2_submission_original_sample_id 633
_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 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.783
####################################################################### 
# 
# 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_448
_database_code_depnum_ccdc_archive 'CCDC 2044379'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2020-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 F O5 S'
_chemical_formula_sum            'C16 H13 F O5 S'
_chemical_formula_weight         336.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H13 F1 O5 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      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                   6.1490(2)
_cell_length_b                   14.5378(5)
_cell_length_c                   16.3353(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.812(3)
_cell_angle_gamma                90
_cell_volume                     1449.95(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5999
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.7740
_cell_measurement_theta_min      2.5100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_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  0.0304
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.805
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10047
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.839
_diffrn_reflns_theta_min         2.511
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.805
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  66.00   0.50    3.44    --   -5.34  38.00  30.00  148
  2  ω      2.00  76.00   0.50    3.44    --    5.49  57.00 -60.00  148
  3  ω    -26.00  23.00   0.50    3.44    --   -5.34 -99.00-150.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0433176000
_diffrn_orient_matrix_UB_12      0.0109544000
_diffrn_orient_matrix_UB_13      -0.0410519000
_diffrn_orient_matrix_UB_21      -0.0104285000
_diffrn_orient_matrix_UB_22      -0.0475273000
_diffrn_orient_matrix_UB_23      -0.0094015000
_diffrn_orient_matrix_UB_31      -0.1072684000
_diffrn_orient_matrix_UB_32      0.0002706000
_diffrn_orient_matrix_UB_33      0.0118601000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3149
_reflns_number_total             3671
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.351
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.069
_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)+(0.0531P)²+0.4327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1050
_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:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00I(H00I), C00K(H00K),
 C00L(H00L)
2.d Idealised Me refined as rotating group:
 C00N(H00F,H00H,H00J)
;
_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
S001 S 0.43465(5) 0.70896(2) 0.62368(2) 0.01670(11) Uani 1 1 d . . . . .
F002 F 0.61012(17) 0.47793(7) 0.93229(6) 0.0352(2) Uani 1 1 d . . . . .
O003 O 0.28639(14) 0.62202(6) 0.63594(6) 0.0181(2) Uani 1 1 d . . . . .
O004 O 0.28541(17) 0.78382(7) 0.62270(6) 0.0236(2) Uani 1 1 d . . . . .
O005 O 0.05377(17) 0.45190(8) 0.58267(6) 0.0260(2) Uani 1 1 d . . . . .
O006 O 0.55341(17) 0.69253(7) 0.55520(6) 0.0246(2) Uani 1 1 d . . . . .
O007 O -0.19329(16) 0.40704(8) 0.66010(7) 0.0302(3) Uani 1 1 d . . . . .
C008 C 0.5441(2) 0.74027(9) 0.78684(8) 0.0185(3) Uani 1 1 d . . . . .
H008 H 0.400624 0.764659 0.786446 0.022 Uiso 1 1 calc R . . . .
C009 C 0.1560(2) 0.44548(9) 0.73058(9) 0.0199(3) Uani 1 1 d . . . . .
C00A C 0.6182(2) 0.71057(9) 0.71429(8) 0.0162(3) Uani 1 1 d . . . . .
C00B C 0.8298(2) 0.67698(9) 0.71319(9) 0.0193(3) Uani 1 1 d . . . . .
H00B H 0.879509 0.658150 0.662902 0.023 Uiso 1 1 calc R . . . .
C00C C 0.9668(2) 0.67152(10) 0.78684(9) 0.0220(3) Uani 1 1 d . . . . .
H00C H 1.111216 0.648277 0.786890 0.026 Uiso 1 1 calc R . . . .
C00D C 0.5075(2) 0.50103(10) 0.79204(9) 0.0209(3) Uani 1 1 d . . . . .
H00D H 0.643757 0.530364 0.787743 0.025 Uiso 1 1 calc R . . . .
C00E C 0.4577(3) 0.46812(10) 0.86629(9) 0.0242(3) Uani 1 1 d . . . . .
C00F C 0.3538(2) 0.49033(9) 0.72343(8) 0.0187(3) Uani 1 1 d . . . . .
C00G C 0.3889(2) 0.53004(9) 0.64138(8) 0.0187(3) Uani 1 1 d . . . . .
H00G H 0.549163 0.535190 0.636713 0.022 Uiso 1 1 calc R . . . .
C00H C -0.0074(2) 0.43224(10) 0.65719(9) 0.0219(3) Uani 1 1 d . . . . .
C00I C 0.6834(2) 0.73368(10) 0.86002(9) 0.0213(3) Uani 1 1 d . . . . .
H00I H 0.633293 0.752615 0.910203 0.026 Uiso 1 1 calc R . . . .
C00J C 0.8957(2) 0.69967(10) 0.86087(9) 0.0224(3) Uani 1 1 d . . . . .
C00K C 0.1094(2) 0.41430(10) 0.80728(10) 0.0253(3) Uani 1 1 d . . . . .
H00K H -0.026423 0.384964 0.812312 0.030 Uiso 1 1 calc R . . . .
C00L C 0.2614(3) 0.42612(11) 0.87621(10) 0.0281(3) Uani 1 1 d . . . . .
H00L H 0.231176 0.405809 0.928967 0.034 Uiso 1 1 calc R . . . .
C00M C 0.2793(2) 0.47252(10) 0.57264(9) 0.0234(3) Uani 1 1 d . . . . .
H00A H 0.284137 0.505421 0.519826 0.028 Uiso 1 1 calc R . . . .
H00E H 0.361172 0.414184 0.569886 0.028 Uiso 1 1 calc R . . . .
C00N C 1.0470(3) 0.69434(13) 0.94009(11) 0.0362(4) Uani 1 1 d . . . . .
H00F H 1.089957 0.630198 0.951151 0.054 Uiso 1 1 calc GR . . . .
H00H H 0.971913 0.717856 0.985442 0.054 Uiso 1 1 calc GR . . . .
H00J H 1.177933 0.731484 0.935302 0.054 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
S001 O003 1.5850(10) . ?
S001 O004 1.4223(10) . ?
S001 O006 1.4267(11) . ?
S001 C00A 1.7520(14) . ?
F002 C00E 1.3496(17) . ?
O003 C00G 1.4765(16) . ?
O005 C00H 1.3466(18) . ?
O005 C00M 1.4471(17) . ?
O007 C00H 1.2068(18) . ?
C008 C00A 1.3882(19) . ?
C008 C00I 1.3887(19) . ?
C009 C00F 1.3967(19) . ?
C009 C00H 1.483(2) . ?
C009 C00K 1.394(2) . ?
C00A C00B 1.3919(19) . ?
C00B C00C 1.3866(19) . ?
C00C C00J 1.395(2) . ?
C00D C00E 1.372(2) . ?
C00D C00F 1.387(2) . ?
C00E C00L 1.379(2) . ?
C00F C00G 1.4983(19) . ?
C00G C00M 1.4949(19) . ?
C00I C00J 1.394(2) . ?
C00J C00N 1.504(2) . ?
C00K C00L 1.386(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
O003 S001 C00A 103.09(6) . . ?
O004 S001 O003 103.39(6) . . ?
O004 S001 O006 120.59(7) . . ?
O004 S001 C00A 110.45(6) . . ?
O006 S001 O003 108.73(6) . . ?
O006 S001 C00A 109.04(6) . . ?
C00G O003 S001 118.81(8) . . ?
C00H O005 C00M 121.36(11) . . ?
C00A C008 C00I 118.81(12) . . ?
C00F C009 C00H 120.40(13) . . ?
C00K C009 C00F 120.06(13) . . ?
C00K C009 C00H 119.53(13) . . ?
C008 C00A S001 118.78(10) . . ?
C008 C00A C00B 121.49(13) . . ?
C00B C00A S001 119.60(10) . . ?
C00C C00B C00A 118.78(13) . . ?
C00B C00C C00J 120.97(13) . . ?
C00E C00D C00F 118.24(14) . . ?
F002 C00E C00D 117.57(14) . . ?
F002 C00E C00L 119.16(13) . . ?
C00D C00E C00L 123.27(14) . . ?
C009 C00F C00G 118.31(12) . . ?
C00D C00F C009 120.10(13) . . ?
C00D C00F C00G 121.52(13) . . ?
O003 C00G C00F 107.27(10) . . ?
O003 C00G C00M 108.06(11) . . ?
C00M C00G C00F 110.87(12) . . ?
O005 C00H C009 117.93(12) . . ?
O007 C00H O005 117.86(13) . . ?
O007 C00H C009 124.18(14) . . ?
C008 C00I C00J 120.94(13) . . ?
C00C C00J C00N 120.33(14) . . ?
C00I C00J C00C 119.00(13) . . ?
C00I C00J C00N 120.67(14) . . ?
C00L C00K C009 119.94(14) . . ?
C00E C00L C00K 118.33(14) . . ?
O005 C00M C00G 112.56(12) . . ?

_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 1.135
_oxdiff_exptl_absorpt_empirical_full_min 0.822
####################################################################### 
# 
# 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_1058
_database_code_depnum_ccdc_archive 'CCDC 2044392'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2020-05-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N O7 S'
_chemical_formula_sum            'C16 H13 N O7 S'
_chemical_formula_weight         363.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H13 N1 O7 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.6324(3)
_cell_length_b                   7.12450(10)
_cell_length_c                   16.0400(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1557.87(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5080
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.9450
_cell_measurement_theta_min      5.5010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7903
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.308
_diffrn_reflns_theta_min         5.516
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    0.17    --  -42.80  30.00  14.00   52
  2  ω    -34.00  18.00   0.50    0.17    --  -42.80  57.00 -30.00  104
  3  ω    -21.00  65.00   0.50    0.17    --   42.80 -57.00 150.00  172
  4  ω     32.00  57.00   0.50    0.68    --   76.50 -94.00  41.00   50
  5  ω     81.00 112.00   0.50    0.17    --   42.80 125.00 -90.00   62
  6  ω    -72.00 -37.00   0.50    0.68    -- -106.00 125.00  30.00   70
  7  ω    -70.00 -33.00   0.50    0.68    -- -106.00  57.00  30.00   74
  8  ω    -82.00 -33.00   0.50    0.68    -- -106.00  37.00  30.00   98
  9  ω    -88.00 -43.00   0.50    0.68    -- -106.00  94.00 152.00   90
 10  ω    -71.00 -32.00   0.50    0.68    -- -106.00  57.00 150.00   78
 11  ω    -79.00 -53.00   0.50    0.68    -- -106.00 125.00 150.00   52
 12  ω   -120.00 -88.00   0.50    0.68    -- -106.00  37.00  30.00   64
 13  ω   -115.00 -90.00   0.50    0.68    -- -106.00  57.00  30.00   50
 14  ω   -110.00 -85.00   0.50    0.68    -- -106.00 125.00   0.00   50
 15  ω    -88.00 -63.00   0.50    0.68    -- -106.00  57.00 -90.00   50
 16  ω    -89.00 -64.00   0.50    0.68    -- -106.00 122.00-129.00   50
 17  ω   -107.00 -82.00   0.50    0.68    -- -106.00 125.00-120.00   50
 18  ω   -122.00 -97.00   0.50    0.68    -- -106.00  57.00 -90.00   50
 19  ω   -170.00-132.00   0.50    0.68    -- -106.00 -30.00-146.00   76
 20  ω   -177.00 -88.00   0.50    0.68    -- -106.00 -57.00 -60.00  178
 21  ω   -174.00-142.00   0.50    0.68    -- -106.00 -99.00 -30.00   64
 22  ω   -127.00 -86.00   0.50    0.68    -- -106.00  57.00 150.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0131724000
_diffrn_orient_matrix_UB_12      -0.0338579000
_diffrn_orient_matrix_UB_13      -0.0941946000
_diffrn_orient_matrix_UB_21      -0.1039826000
_diffrn_orient_matrix_UB_22      0.0766897000
_diffrn_orient_matrix_UB_23      -0.0159682000
_diffrn_orient_matrix_UB_31      0.0422240000
_diffrn_orient_matrix_UB_32      0.1993411000
_diffrn_orient_matrix_UB_33      -0.0098519000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.742
_reflns_Friedel_fraction_max     0.709
_reflns_number_gt                2628
_reflns_number_total             2719
_reflns_odcompleteness_completeness 98.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (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         0.270
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.048
_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)+(0.0837P)²+0.2073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00E(H00E), C00H(H00H), C00J(H00J), C00K(H00K), C00M(H00M),
 C00O(H00O)
2.d Idealised Me refined as rotating group:
 C00P(H00D,H00F,H00I)
;
_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
S001 S 0.27507(5) 0.29740(9) 0.57280(6) 0.0277(2) Uani 1 1 d . . . . .
O002 O 0.4050(2) 0.3354(4) 0.33593(19) 0.0385(6) Uani 1 1 d . . . . .
O003 O 0.3331(2) 0.1989(4) 0.6326(2) 0.0413(7) Uani 1 1 d . . . . .
O004 O 0.5535(2) 0.4125(4) 0.2938(2) 0.0427(7) Uani 1 1 d . . . . .
O005 O 0.35493(16) 0.3951(3) 0.51466(17) 0.0289(5) Uani 1 1 d . . . . .
O006 O 0.68723(19) 1.0379(4) 0.3605(2) 0.0396(6) Uani 1 1 d . . . . .
O007 O 0.2078(2) 0.1947(3) 0.5229(2) 0.0362(6) Uani 1 1 d . . . . .
N10 N 0.6203(2) 1.0707(4) 0.4094(2) 0.0314(6) Uani 1 1 d . . . . .
O8 O 0.6152(2) 1.2112(4) 0.4526(2) 0.0426(7) Uani 1 1 d . . . . .
C00A C 0.3959(2) 0.6661(4) 0.4355(2) 0.0250(6) Uani 1 1 d . . . . .
C00B C 0.1144(3) 0.5085(5) 0.6082(2) 0.0309(7) Uani 1 1 d . . . . .
H00B H 0.077331 0.414848 0.580210 0.037 Uiso 1 1 calc R . . . .
C00C C 0.4815(3) 0.4550(5) 0.3317(2) 0.0313(7) Uani 1 1 d . . . . .
C00D C 0.5406(2) 0.9311(4) 0.4165(2) 0.0265(7) Uani 1 1 d . . . . .
C00E C 0.4657(3) 0.9649(5) 0.4726(2) 0.0288(7) Uani 1 1 d . . . . .
H00E H 0.464522 1.077107 0.504606 0.035 Uiso 1 1 calc R . . . .
C00F C 0.2154(2) 0.4893(4) 0.6178(2) 0.0254(6) Uani 1 1 d . . . . .
C00G C 0.3204(2) 0.5136(4) 0.4453(2) 0.0272(7) Uani 1 1 d . . . . .
H00G H 0.255432 0.570179 0.459756 0.033 Uiso 1 1 calc R . . . .
C00H C 0.2710(3) 0.6230(5) 0.6598(2) 0.0350(8) Uani 1 1 d . . . . .
H00H H 0.339380 0.605710 0.668158 0.042 Uiso 1 1 calc R . . . .
C00I C 0.4725(2) 0.6352(4) 0.3794(2) 0.0262(7) Uani 1 1 d . . . . .
C00J C 0.5461(2) 0.7698(5) 0.3690(2) 0.0265(6) Uani 1 1 d . . . . .
H00J H 0.598185 0.750866 0.330591 0.032 Uiso 1 1 calc R . . . .
C00K C 0.3920(2) 0.8312(5) 0.4813(2) 0.0281(7) Uani 1 1 d . . . . .
H00K H 0.339022 0.852912 0.518545 0.034 Uiso 1 1 calc R . . . .
C00L C 0.1221(4) 0.8070(5) 0.6785(3) 0.0444(11) Uani 1 1 d . . . . .
C00M C 0.0689(3) 0.6673(5) 0.6403(3) 0.0382(8) Uani 1 1 d . . . . .
H00M H -0.000267 0.679732 0.635739 0.046 Uiso 1 1 calc R . . . .
C00N C 0.3116(3) 0.4002(5) 0.3664(3) 0.0356(8) Uani 1 1 d . . . . .
H00A H 0.268752 0.290492 0.376920 0.043 Uiso 1 1 calc R . . . .
H00C H 0.279917 0.478034 0.322878 0.043 Uiso 1 1 calc R . . . .
C00O C 0.2237(4) 0.7823(5) 0.6891(3) 0.0463(12) Uani 1 1 d . . . . .
H00O H 0.260607 0.876443 0.716955 0.056 Uiso 1 1 calc R . . . .
C00P C 0.0731(6) 0.9855(6) 0.7067(4) 0.071(2) Uani 1 1 d . . . . .
H00D H 0.087070 1.085940 0.666746 0.107 Uiso 1 1 calc GR . . . .
H00F H 0.098195 1.020891 0.761773 0.107 Uiso 1 1 calc GR . . . .
H00I H 0.002043 0.965628 0.710065 0.107 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
S001 O003 1.428(3) . ?
S001 O005 1.594(2) . ?
S001 O007 1.421(3) . ?
S001 C00F 1.747(3) . ?
O002 C00C 1.349(5) . ?
O002 C00N 1.440(5) . ?
O004 C00C 1.195(5) . ?
O005 C00G 1.473(4) . ?
O006 N10 1.226(4) . ?
N10 O8 1.219(4) . ?
N10 C00D 1.477(4) . ?
C00A C00G 1.505(4) . ?
C00A C00I 1.395(5) . ?
C00A C00K 1.388(5) . ?
C00B C00F 1.392(5) . ?
C00B C00M 1.389(5) . ?
C00C C00I 1.499(5) . ?
C00D C00E 1.382(5) . ?
C00D C00J 1.381(5) . ?
C00E C00K 1.391(5) . ?
C00F C00H 1.391(5) . ?
C00G C00N 1.508(6) . ?
C00H C00O 1.388(6) . ?
C00I C00J 1.398(4) . ?
C00L C00M 1.375(7) . ?
C00L C00O 1.406(8) . ?
C00L C00P 1.507(6) . ?

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
O003 S001 O005 103.24(14) . . ?
O003 S001 C00F 111.42(19) . . ?
O005 S001 C00F 102.60(14) . . ?
O007 S001 O003 118.90(17) . . ?
O007 S001 O005 109.66(16) . . ?
O007 S001 C00F 109.59(16) . . ?
C00C O002 C00N 119.9(3) . . ?
C00G O005 S001 118.27(19) . . ?
O006 N10 C00D 118.0(3) . . ?
O8 N10 O006 124.2(3) . . ?
O8 N10 C00D 117.9(3) . . ?
C00I C00A C00G 117.7(3) . . ?
C00K C00A C00G 122.0(3) . . ?
C00K C00A C00I 120.2(3) . . ?
C00M C00B C00F 118.7(3) . . ?
O002 C00C C00I 116.9(3) . . ?
O004 C00C O002 120.1(3) . . ?
O004 C00C C00I 123.0(3) . . ?
C00E C00D N10 118.4(3) . . ?
C00J C00D N10 118.5(3) . . ?
C00J C00D C00E 123.0(3) . . ?
C00D C00E C00K 118.6(3) . . ?
C00B C00F S001 119.5(3) . . ?
C00H C00F S001 118.8(3) . . ?
C00H C00F C00B 121.6(3) . . ?
O005 C00G C00A 105.9(3) . . ?
O005 C00G C00N 110.6(3) . . ?
C00A C00G C00N 110.7(3) . . ?
C00O C00H C00F 118.1(4) . . ?
C00A C00I C00C 121.7(3) . . ?
C00A C00I C00J 120.4(3) . . ?
C00J C00I C00C 117.9(3) . . ?
C00D C00J C00I 117.8(3) . . ?
C00A C00K C00E 120.0(3) . . ?
C00M C00L C00O 118.9(4) . . ?
C00M C00L C00P 120.7(5) . . ?
C00O C00L C00P 120.4(5) . . ?
C00L C00M C00B 121.2(4) . . ?
O002 C00N C00G 112.7(3) . . ?
C00H C00O C00L 121.2(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 3.167
_oxdiff_exptl_absorpt_empirical_full_min 0.432
####################################################################### 
# 
# 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_xcalibur_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2044394'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C19 H20 B F4 I N2 O4'
_chemical_formula_moiety         'C19 H20 B F4 I N2 O4'
_chemical_formula_weight         554.09
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+Y,1/2-Z
5 -X,-Y,-Z
6 +X,-Y,-1/2+Z
7 -1/2-X,-1/2-Y,-Z
8 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   23.8548(10)
_cell_length_b                   8.5878(3)
_cell_length_c                   22.9628(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 112.852(5)
_cell_angle_gamma                90.0000
_cell_volume                     4334.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11831
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      30.82
_cell_measurement_temperature    433
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_colour            nONE
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2192.00
_exptl_absorpt_coefficient_mu    1.540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      433
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            20700
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_theta_max         30.86
_diffrn_reflns_theta_min         2.090
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_max 0.805
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5515
_reflns_number_gt                4886
_reflns_threshold_expression     F>2.0σ(F)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F > 2.0 sigma(F).
    The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are 
    based on F, with F set to zero for negative F. The threshold expression of
    F > 2.0 sigma(F) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4886
_refine_ls_number_parameters     300
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[0.0178Fo² + 1.0000σ(Fo²)]'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         3.900
_refine_diff_density_min         -4.910
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.553170(10) 0.76169(3) 0.504070(10) 0.02330(13) Uani 1 8 d . . .
F3 F 0.88383(19) 1.2268(5) 0.6988(2) 0.0573(11) Uani 1 8 d . . .
F17 F 0.7935(2) 1.1030(8) 0.6628(2) 0.1037(18) Uani 1 8 d . . .
F21 F 0.8623(2) 1.0126(6) 0.6409(2) 0.0878(16) Uani 1 8 d . . .
F34 F 0.8272(4) 1.2263(6) 0.5916(3) 0.095(2) Uani 1 8 d . . .
O2 O 0.46231(14) 0.6819(5) 0.54455(17) 0.0419(10) Uani 1 8 d . . .
O7 O 0.57178(12) 0.8644(4) 0.42821(13) 0.0317(8) Uani 1 8 d . . .
O8 O 0.47759(12) 0.9510(5) 0.40615(14) 0.0389(8) Uani 1 8 d . . .
O9 O 0.56175(12) 0.6430(4) 0.59024(13) 0.0318(8) Uani 1 8 d . . .
N5 N 0.67448(13) 0.9023(4) 0.67028(14) 0.0222(7) Uani 1 8 d . . .
N10 N 0.66356(13) 1.0681(4) 0.59321(15) 0.0226(7) Uani 1 8 d . . .
C4 C 0.5261(3) 1.0181(8) 0.3362(2) 0.0526(16) Uani 1 8 d . . .
C6 C 0.65504(16) 1.1501(5) 0.64063(19) 0.0242(9) Uani 1 8 d . . .
C11 C 0.69081(18) 0.7892(5) 0.57746(18) 0.0203(9) Uani 1 8 d . . .
C12 C 0.67570(15) 0.9176(4) 0.61199(16) 0.0198(8) Uani 1 8 d . . .
C13 C 0.66248(17) 1.0452(5) 0.68937(18) 0.0258(9) Uani 1 8 d . . .
C14 C 0.76514(17) 0.6226(5) 0.56578(19) 0.0284(10) Uani 1 8 d . . .
C15 C 0.66418(18) 1.1338(5) 0.5344(2) 0.0305(10) Uani 1 8 d . . .
C16 C 0.7517(2) 0.7509(4) 0.5933(3) 0.0257(12) Uani 1 8 d . . .
C18 C 0.6880(3) 0.7594(4) 0.7072(3) 0.0300(12) Uani 1 8 d . . .
C19 C 0.6397(3) 1.2431(5) 0.7488(3) 0.0389(14) Uani 1 8 d . . .
C20 C 0.65917(17) 0.5721(5) 0.50467(17) 0.0250(9) Uani 1 8 d . . .
C22 C 0.72033(18) 0.5323(5) 0.52232(18) 0.0274(10) Uani 1 8 d . . .
C23 C 0.64512(16) 0.6997(5) 0.53239(18) 0.0212(8) Uani 1 8 d . . .
C24 C 0.65381(18) 1.0878(5) 0.74453(19) 0.0315(10) Uani 1 8 d . . .
C25 C 0.63619(19) 1.3481(6) 0.7005(2) 0.0371(11) Uani 1 8 d . . .
C26 C 0.64314(19) 1.3068(6) 0.6459(2) 0.0328(11) Uani 1 8 d . . .
C27 C 0.50680(18) 0.6342(6) 0.5898(2) 0.0334(11) Uani 1 8 d . . .
C28 C 0.5009(2) 0.5609(7) 0.6469(2) 0.0472(15) Uani 1 8 d . . .
C29 C 0.52281(17) 0.9417(5) 0.39252(18) 0.0307(10) Uani 1 8 d . . .
B32 B 0.8377(2) 1.1634(9) 0.6485(3) 0.0452(16) Uani 1 8 d . . .
H1 H 0.80565 0.59616 0.57589 0.0356 Uiso 1 8 calc R . .
H2 H 0.78243 0.80948 0.62282 0.0310 Uiso 1 8 calc R . .
H3 H 0.63292 1.2772 0.78395 0.0433 Uiso 1 8 calc R . .
H4 H 0.62889 0.51346 0.4746 0.0306 Uiso 1 8 calc R . .
H5 H 0.73083 0.44498 0.50479 0.0365 Uiso 1 8 calc R . .
H6 H 0.65712 1.0165 0.77617 0.0380 Uiso 1 8 calc R . .
H7 H 0.62882 1.45201 0.70643 0.0421 Uiso 1 8 calc R . .
H8 H 0.63918 1.3769 0.61372 0.0393 Uiso 1 8 calc R . .
H9 H 0.5209 1.12869 0.33755 0.0625 Uiso 1 8 calc R . .
H10 H 0.56556 0.99624 0.33614 0.0626 Uiso 1 8 calc R . .
H11 H 0.49533 0.97653 0.29859 0.0626 Uiso 1 8 calc R . .
H12 H 0.63548 1.07938 0.49877 0.0359 Uiso 1 8 calc R . .
H13 H 0.65337 1.24201 0.5318 0.0358 Uiso 1 8 calc R . .
H14 H 0.70419 1.12347 0.53425 0.0362 Uiso 1 8 calc R . .
H15 H 0.72875 0.72599 0.71516 0.0389 Uiso 1 8 calc R . .
H16 H 0.68411 0.77791 0.74671 0.0391 Uiso 1 8 calc R . .
H17 H 0.65984 0.67987 0.68424 0.0391 Uiso 1 8 calc R . .
H18 H 0.47544 0.47034 0.63455 0.0579 Uiso 1 8 calc R . .
H19 H 0.54067 0.53144 0.67627 0.0581 Uiso 1 8 calc R . .
H20 H 0.48353 0.63472 0.66644 0.0579 Uiso 1 8 calc R . .



#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
I1 O7 2.147(3) yes .
I1 O9 2.164(3) yes .
I1 C23 2.100(4) yes .
F3 B32 1.361(6) yes .
F17 B32 1.327(9) yes .
F21 B32 1.460(9) yes .
F34 B32 1.344(9) yes .
O2 C27 1.232(5) yes .
O7 C29 1.316(5) yes .
O8 C29 1.237(6) yes .
O9 C27 1.309(6) yes .
N5 C12 1.356(5) yes .
N5 C13 1.371(6) yes .
N5 C18 1.455(5) yes .
N10 C6 1.376(6) yes .
N10 C12 1.358(5) yes .
N10 C15 1.469(6) yes .
C4 C29 1.478(8) yes .
C6 C13 1.393(6) yes .
C6 C26 1.390(6) yes .
C11 C12 1.482(6) yes .
C11 C16 1.393(7) yes .
C11 C23 1.405(5) yes .
C13 C24 1.409(7) yes .
C14 C16 1.368(7) yes .
C14 C22 1.383(5) yes .
C19 C24 1.388(7) yes .
C19 C25 1.406(8) yes .
C20 C22 1.397(6) yes .
C20 C23 1.373(6) yes .
C25 C26 1.373(8) yes .
C27 C28 1.507(8) yes .
C4 H9 0.960 no .
C4 H10 0.960 no .
C4 H11 0.960 no .
C14 H1 0.930 no .
C15 H12 0.960 no .
C15 H13 0.960 no .
C15 H14 0.960 no .
C16 H2 0.930 no .
C18 H15 0.960 no .
C18 H16 0.960 no .
C18 H17 0.960 no .
C19 H3 0.930 no .
C20 H4 0.930 no .
C22 H5 0.930 no .
C24 H6 0.930 no .
C25 H7 0.930 no .
C26 H8 0.930 no .
C28 H18 0.960 no .
C28 H19 0.960 no .
C28 H20 0.960 no .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O7 I1 O9 163.65(10) yes . .
O7 I1 C23 80.51(14) yes . .
O9 I1 C23 83.17(14) yes . .
I1 O7 C29 107.4(3) yes . .
I1 O9 C27 106.4(2) yes . .
C12 N5 C13 108.4(3) yes . .
C12 N5 C18 124.9(4) yes . .
C13 N5 C18 126.6(4) yes . .
C6 N10 C12 108.3(3) yes . .
C6 N10 C15 126.0(3) yes . .
C12 N10 C15 125.5(4) yes . .
N10 C6 C13 107.0(3) yes . .
N10 C6 C26 131.5(4) yes . .
C13 C6 C26 121.5(4) yes . .
C12 C11 C16 118.8(3) yes . .
C12 C11 C23 121.4(4) yes . .
C16 C11 C23 119.6(4) yes . .
N5 C12 N10 108.8(3) yes . .
N5 C12 C11 124.0(3) yes . .
N10 C12 C11 127.2(4) yes . .
N5 C13 C6 107.4(4) yes . .
N5 C13 C24 129.9(4) yes . .
C6 C13 C24 122.5(4) yes . .
C16 C14 C22 122.1(4) yes . .
C11 C16 C14 118.5(4) yes . .
C24 C19 C25 120.1(6) yes . .
C22 C20 C23 118.5(3) yes . .
C14 C22 C20 120.0(4) yes . .
I1 C23 C11 120.5(3) yes . .
I1 C23 C20 118.2(2) yes . .
C11 C23 C20 121.3(4) yes . .
C13 C24 C19 115.9(5) yes . .
C19 C25 C26 124.2(5) yes . .
C6 C26 C25 115.5(5) yes . .
O2 C27 O9 121.2(5) yes . .
O2 C27 C28 122.1(4) yes . .
O9 C27 C28 116.6(3) yes . .
O7 C29 O8 121.7(4) yes . .
O7 C29 C4 115.6(4) yes . .
O8 C29 C4 122.7(4) yes . .
F3 B32 F17 113.9(5) yes . .
F3 B32 F21 103.1(4) yes . .
F3 B32 F34 116.6(6) yes . .
F17 B32 F21 94.5(6) yes . .
F17 B32 F34 122.1(5) yes . .
F21 B32 F34 99.9(5) yes . .
C29 C4 H9 111.104 no . .
C29 C4 H10 107.498 no . .
C29 C4 H11 109.900 no . .
H9 C4 H10 109.436 no . .
H9 C4 H11 109.429 no . .
H10 C4 H11 109.441 no . .
C16 C14 H1 119.217 no . .
C22 C14 H1 118.719 no . .
N10 C15 H12 109.753 no . .
N10 C15 H13 109.311 no . .
N10 C15 H14 109.436 no . .
H12 C15 H13 109.443 no . .
H12 C15 H14 109.446 no . .
H13 C15 H14 109.438 no . .
C11 C16 H2 120.577 no . .
C14 C16 H2 120.859 no . .
N5 C18 H15 109.990 no . .
N5 C18 H16 109.261 no . .
N5 C18 H17 109.252 no . .
H15 C18 H16 109.440 no . .
H15 C18 H17 109.443 no . .
H16 C18 H17 109.440 no . .
C24 C19 H3 119.519 no . .
C25 C19 H3 120.336 no . .
C22 C20 H4 120.350 no . .
C23 C20 H4 121.175 no . .
C14 C22 H5 120.122 no . .
C20 C22 H5 119.901 no . .
C13 C24 H6 122.256 no . .
C19 C24 H6 121.807 no . .
C19 C25 H7 117.195 no . .
C26 C25 H7 118.561 no . .
C6 C26 H8 121.213 no . .
C25 C26 H8 123.219 no . .
C27 C28 H18 110.158 no . .
C27 C28 H19 108.795 no . .
C27 C28 H20 109.541 no . .
H18 C28 H19 109.443 no . .
H18 C28 H20 109.439 no . .
H19 C28 H20 109.448 no . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O7 I1 C23 C11 97.5(3) no . . . .
O7 I1 C23 C20 -81.1(3) no . . . .
C23 I1 O7 C29 -174.9(2) no . . . .
O9 I1 C23 C11 -81.5(3) no . . . .
O9 I1 C23 C20 99.9(3) no . . . .
C23 I1 O9 C27 -172.0(2) no . . . .
I1 O7 C29 O8 2.6(5) no . . . .
I1 O7 C29 C4 -178.5(2) no . . . .
I1 O9 C27 O2 3.2(5) no . . . .
I1 O9 C27 C28 -177.7(3) no . . . .
C12 N5 C13 C6 1.1(4) no . . . .
C12 N5 C13 C24 176.6(3) no . . . .
C13 N5 C12 N10 -1.1(4) no . . . .
C13 N5 C12 C11 176.4(3) no . . . .
C18 N5 C12 N10 -177.1(3) no . . . .
C18 N5 C12 C11 0.4(5) no . . . .
C18 N5 C13 C6 177.1(4) no . . . .
C18 N5 C13 C24 -7.5(6) no . . . .
C6 N10 C12 N5 0.6(3) no . . . .
C6 N10 C12 C11 -176.8(3) no . . . .
C12 N10 C6 C13 0.1(3) no . . . .
C12 N10 C6 C26 178.2(3) no . . . .
C15 N10 C6 C13 -175.5(3) no . . . .
C15 N10 C6 C26 2.5(6) no . . . .
C15 N10 C12 N5 176.2(3) no . . . .
C15 N10 C12 C11 -1.1(5) no . . . .
N10 C6 C13 N5 -0.8(4) no . . . .
N10 C6 C13 C24 -176.6(3) no . . . .
N10 C6 C26 C25 178.9(3) no . . . .
C13 C6 C26 C25 -3.3(5) no . . . .
C26 C6 C13 N5 -179.1(3) no . . . .
C26 C6 C13 C24 5.1(5) no . . . .
C12 C11 C16 C14 173.5(4) no . . . .
C16 C11 C12 N5 -79.7(5) no . . . .
C16 C11 C12 N10 97.3(5) no . . . .
C12 C11 C23 I1 7.5(6) no . . . .
C12 C11 C23 C20 -174.0(3) no . . . .
C23 C11 C12 N5 96.1(4) no . . . .
C23 C11 C12 N10 -86.9(5) no . . . .
C16 C11 C23 I1 -176.7(4) no . . . .
C16 C11 C23 C20 1.8(7) no . . . .
C23 C11 C16 C14 -2.4(7) no . . . .
N5 C13 C24 C19 -177.4(3) no . . . .
C6 C13 C24 C19 -2.5(5) no . . . .
C16 C14 C22 C20 0.8(7) no . . . .
C22 C14 C16 C11 1.1(7) no . . . .
C24 C19 C25 C26 3.2(7) no . . . .
C25 C19 C24 C13 -1.5(7) no . . . .
C22 C20 C23 I1 178.7(3) no . . . .
C22 C20 C23 C11 0.1(6) no . . . .
C23 C20 C22 C14 -1.4(6) no . . . .
C19 C25 C26 C6 -0.8(6) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
I1 O2 2.756(4) no . .
I1 O8 2.793(3) no . .
I1 C12 3.294(3) no . .
O7 C11 3.559(4) no . .
O7 C15 3.461(5) no . .
O7 C20 3.300(5) no . .
O9 N5 3.424(4) no . .
O9 C11 3.441(6) no . .
O9 C12 3.485(5) no . .
O9 C18 3.317(5) no . .
N5 C16 3.278(7) no . .
N5 C23 3.438(5) no . .
N5 C26 3.551(6) no . .
N10 C16 3.441(6) no . .
N10 C23 3.417(5) no . .
N10 C24 3.576(6) no . .
C6 C19 2.765(9) no . .
C11 C15 3.106(6) no . .
C11 C18 3.017(8) no . .
C11 C22 2.768(6) no . .
C12 C24 3.593(6) no . .
C12 C26 3.585(6) no . .
C13 C25 2.711(6) no . .
C14 C23 2.742(5) no . .
C15 C26 3.165(8) no . .
C16 C18 3.500(10) no . .
C16 C20 2.807(6) no . .
C18 C24 3.146(7) no . .
C24 C26 2.877(7) no . .
I1 O8 3.472(4) no . 5_676
F3 C4 3.377(8) no . 7_786
F3 C18 3.248(9) no . 4_656
F17 N5 3.382(7) no . .
F17 N10 2.899(5) no . .
F17 C6 3.166(6) no . .
F17 C12 3.041(6) no . .
F17 C13 3.445(7) no . .
F17 C15 3.349(5) no . .
F17 C16 3.384(7) no . .
F17 C18 3.143(8) no . 4_656
F21 C16 3.312(7) no . .
F21 C19 3.446(8) no . 4_646
F21 C20 3.261(6) no . 7_776
F21 C22 3.513(6) no . 7_776
F21 C28 3.282(8) no . 3_555
F34 C15 3.213(8) no . 7_786
F34 C20 3.481(8) no . 7_776
F34 C22 3.576(7) no . 1_565
F34 C22 3.280(7) no . 7_776
O2 O8 3.467(5) no . 5_676
O2 C15 3.263(5) no . 5_676
O2 C20 3.448(5) no . 5_666
O2 C29 3.502(6) no . 5_676
O8 I1 3.472(4) no . 5_676
O8 O2 3.467(5) no . 5_676
O8 N5 3.589(4) no . 5_676
O8 N10 3.377(5) no . 5_676
O8 C6 3.046(5) no . 5_676
O8 C13 3.207(4) no . 5_676
O8 C26 3.457(5) no . 5_676
O8 C27 3.579(6) no . 5_676
O9 C25 3.534(5) no . 1_545
O9 C26 3.438(5) no . 1_545
N5 F17 3.382(7) no . .
N5 O8 3.589(4) no . 5_676
N10 F17 2.899(5) no . .
N10 O8 3.377(5) no . 5_676
C4 F3 3.377(8) no . 7_786
C6 F17 3.166(6) no . .
C6 O8 3.046(5) no . 5_676
C12 F17 3.041(6) no . .
C13 F17 3.445(7) no . .
C13 O8 3.207(4) no . 5_676
C14 C14 3.570(6) no . 7_776
C15 F17 3.349(5) no . .
C15 F34 3.213(8) no . 7_786
C15 O2 3.263(5) no . 5_676
C16 F17 3.384(7) no . .
C16 F21 3.312(7) no . .
C16 C19 3.546(7) no . 4_646
C16 C22 3.512(8) no . 7_776
C18 F3 3.248(9) no . 4_646
C18 F17 3.143(8) no . 4_646
C19 F21 3.446(8) no . 4_656
C19 C16 3.546(7) no . 4_656
C20 F21 3.261(6) no . 7_776
C20 F34 3.481(8) no . 7_776
C20 O2 3.448(5) no . 5_666
C22 F21 3.513(6) no . 7_776
C22 F34 3.576(7) no . 1_545
C22 F34 3.280(7) no . 7_776
C22 C16 3.512(8) no . 7_776
C25 O9 3.534(5) no . 1_565
C25 C28 3.490(7) no . 1_565
C26 O8 3.457(5) no . 5_676
C26 O9 3.438(5) no . 1_565
C27 O8 3.579(6) no . 5_676
C28 F21 3.282(8) no . 3_445
C28 C25 3.490(7) no . 1_545
C29 O2 3.502(6) no . 5_676
I1 H4 3.0355 no . .
I1 H12 3.3910 no . .
O2 H18 2.6769 no . .
O2 H19 3.1496 no . .
O2 H20 2.6746 no . .
O7 H4 3.3089 no . .
O7 H9 2.9991 no . .
O7 H10 2.3514 no . .
O7 H11 2.9826 no . .
O7 H12 2.5356 no . .
O8 H9 2.6723 no . .
O8 H10 3.1240 no . .
O8 H11 2.6719 no . .
O9 H17 2.5123 no . .
O9 H18 3.0168 no . .
O9 H19 2.4178 no . .
O9 H20 3.0140 no . .
N5 H2 3.2610 no . .
N5 H6 2.7979 no . .
N10 H2 3.4551 no . .
N10 H8 2.7939 no . .
C6 H6 3.2993 no . .
C6 H7 3.1831 no . .
C6 H12 3.1650 no . .
C6 H13 2.6063 no . .
C6 H14 3.1014 no . .
C11 H1 3.2143 no . .
C11 H4 3.2649 no . .
C11 H12 3.0600 no . .
C11 H14 3.0938 no . .
C11 H15 2.9815 no . .
C11 H17 2.9744 no . .
C12 H2 2.6295 no . .
C12 H12 2.7700 no . .
C12 H13 3.2672 no . .
C12 H14 2.7779 no . .
C12 H15 2.7555 no . .
C12 H16 3.2507 no . .
C12 H17 2.7479 no . .
C13 H3 3.2206 no . .
C13 H8 3.2696 no . .
C13 H15 3.1046 no . .
C13 H16 2.5965 no . .
C13 H17 3.1395 no . .
C14 H4 3.2466 no . .
C15 H8 2.9791 no . .
C16 H5 3.2388 no . .
C16 H14 3.4878 no . .
C16 H15 3.0614 no . .
C18 H2 3.5218 no . .
C18 H6 2.9718 no . .
C19 H8 3.3033 no . .
C20 H1 3.2386 no . .
C22 H2 3.2454 no . .
C23 H2 3.2628 no . .
C23 H5 3.2210 no . .
C23 H12 3.3377 no . .
C23 H17 3.3704 no . .
C24 H7 3.2398 no . .
C24 H16 2.7534 no . .
C25 H6 3.2713 no . .
C26 H3 3.2813 no . .
C26 H13 2.7812 no . .
C27 H17 3.4691 no . .
C29 H12 3.0791 no . .
H1 H2 2.2995 no . .
H1 H5 2.2964 no . .
H2 H14 3.4558 no . .
H2 H15 2.9595 no . .
H3 H6 2.3362 no . .
H3 H7 2.3015 no . .
H4 H5 2.3303 no . .
H6 H16 2.3257 no . .
H6 H17 3.5950 no . .
H7 H8 2.3276 no . .
H8 H13 2.3430 no . .
H8 H14 3.5595 no . .
H10 H12 3.5213 no . .
H17 H19 3.0554 no . .
I1 H18 3.5890 no . 5_666
F3 H6 2.8131 no . 4_656
F3 H7 3.3026 no . 4_646
F3 H9 2.9789 no . 7_786
F3 H10 2.9173 no . 7_786
F3 H16 2.4419 no . 4_656
F3 H17 3.2616 no . 4_656
F3 H19 3.2058 no . 4_656
F3 H20 2.8642 no . 3_555
F3 H20 3.5510 no . 4_656
F17 H2 2.6607 no . .
F17 H3 3.2770 no . 4_646
F17 H7 3.1321 no . 4_646
F17 H14 2.8981 no . .
F17 H15 3.2254 no . 4_656
F17 H16 2.4486 no . 4_656
F17 H17 3.3126 no . 4_656
F21 H2 2.4968 no . .
F21 H3 2.6323 no . 4_646
F21 H4 2.7489 no . 7_776
F21 H5 3.2380 no . 7_776
F21 H7 3.4692 no . 4_646
F21 H18 2.7819 no . 3_555
F21 H20 2.9130 no . 3_555
F34 H1 3.2158 no . 1_565
F34 H4 2.9805 no . 7_776
F34 H5 3.0382 no . 1_565
F34 H5 2.5693 no . 7_776
F34 H9 3.5700 no . 7_786
F34 H10 3.4170 no . 7_786
F34 H12 3.0529 no . 7_786
F34 H13 3.0562 no . 7_786
F34 H14 2.8507 no . .
F34 H14 2.9832 no . 7_786
F34 H20 3.5350 no . 3_555
O2 H4 2.6451 no . 5_666
O2 H8 3.5341 no . 5_676
O2 H9 3.0488 no . 5_676
O2 H12 2.9721 no . 5_676
O2 H13 2.7127 no . 5_676
O7 H1 2.9810 no . 7_776
O7 H18 3.2172 no . 5_666
O9 H7 3.0090 no . 1_545
O9 H8 2.8553 no . 1_545
C4 H11 2.9573 no . 2_655
C4 H20 2.9893 no . 5_676
C6 H15 3.4563 no . 4_656
C13 H15 3.0871 no . 4_656
C14 H6 3.4947 no . 4_646
C14 H14 3.4031 no . 7_776
C15 H1 3.4997 no . 7_776
C15 H4 3.5109 no . 1_565
C15 H5 3.3122 no . 1_565
C15 H5 3.0481 no . 7_776
C16 H3 3.0903 no . 4_646
C16 H5 3.5766 no . 7_776
C16 H6 3.5648 no . 4_646
C18 H7 2.9905 no . 1_545
C19 H2 2.8661 no . 4_656
C19 H11 3.5203 no . 5_676
C19 H15 2.9220 no . 4_656
C19 H19 3.3809 no . 1_565
C20 H8 3.1994 no . 1_545
C20 H13 2.9174 no . 1_545
C20 H18 3.5624 no . 5_666
C22 H2 3.5761 no . 7_776
C22 H13 3.0136 no . 1_545
C22 H14 3.5538 no . 1_545
C22 H14 2.9214 no . 7_776
C23 H1 3.5919 no . 7_776
C23 H8 3.3764 no . 1_545
C24 H2 3.4082 no . 4_656
C24 H10 3.5802 no . 6_576
C24 H11 3.3477 no . 5_676
C24 H15 2.8458 no . 4_656
C25 H15 3.2223 no . 4_656
C25 H17 2.9566 no . 1_565
C25 H19 2.6452 no . 1_565
C26 H15 3.5246 no . 4_656
C26 H17 3.3056 no . 1_565
C26 H19 3.3920 no . 1_565
C27 H4 3.2487 no . 5_666
C27 H7 3.4693 no . 1_545
C27 H9 2.8670 no . 5_676
C28 H4 3.3270 no . 5_666
C28 H7 2.9683 no . 1_545
C28 H9 2.7658 no . 5_676
C29 H18 3.5959 no . 5_666
B32 H2 3.2743 no . .
B32 H4 3.5610 no . 7_776
B32 H5 3.3856 no . 7_776
B32 H6 3.4695 no . 4_656
B32 H14 3.2648 no . .
B32 H16 2.8286 no . 4_656
B32 H20 3.3486 no . 3_555
H1 F34 3.2158 no . 1_545
H1 O7 2.9810 no . 7_776
H1 C15 3.4997 no . 7_776
H1 C23 3.5919 no . 7_776
H1 H3 3.3556 no . 4_646
H1 H6 3.2332 no . 4_646
H1 H10 3.0543 no . 7_776
H1 H12 3.0090 no . 7_776
H1 H14 3.0900 no . 7_776
H2 F17 2.6607 no . .
H2 F21 2.4968 no . .
H2 C19 2.8661 no . 4_646
H2 C22 3.5761 no . 7_776
H2 C24 3.4082 no . 4_646
H2 B32 3.2743 no . .
H2 H3 2.3195 no . 4_646
H2 H5 3.5232 no . 7_776
H2 H6 3.3455 no . 4_646
H3 F17 3.2770 no . 4_656
H3 F21 2.6323 no . 4_656
H3 C16 3.0903 no . 4_656
H3 H1 3.3556 no . 4_656
H3 H2 2.3195 no . 4_656
H3 H10 3.3209 no . 6_576
H3 H15 3.3212 no . 4_656
H3 H19 3.3908 no . 1_565
H4 F21 2.7489 no . 7_776
H4 F34 2.9805 no . 7_776
H4 O2 2.6451 no . 5_666
H4 C15 3.5109 no . 1_545
H4 C27 3.2487 no . 5_666
H4 C28 3.3270 no . 5_666
H4 B32 3.5610 no . 7_776
H4 H8 3.3214 no . 1_545
H4 H13 2.6277 no . 1_545
H4 H18 2.7659 no . 5_666
H4 H20 3.5432 no . 5_666
H5 F21 3.2380 no . 7_776
H5 F34 3.0382 no . 1_545
H5 F34 2.5693 no . 7_776
H5 C15 3.3122 no . 1_545
H5 C15 3.0481 no . 7_776
H5 C16 3.5766 no . 7_776
H5 B32 3.3856 no . 7_776
H5 H2 3.5232 no . 7_776
H5 H5 3.5009 no . 7_766
H5 H12 3.2286 no . 7_776
H5 H13 2.7798 no . 1_545
H5 H13 3.5663 no . 7_776
H5 H14 2.9697 no . 1_545
H5 H14 2.1520 no . 7_776
H6 F3 2.8131 no . 4_646
H6 C14 3.4947 no . 4_656
H6 C16 3.5648 no . 4_656
H6 B32 3.4695 no . 4_646
H6 H1 3.2332 no . 4_656
H6 H2 3.3455 no . 4_656
H6 H10 3.0025 no . 6_576
H6 H11 3.3656 no . 5_676
H6 H15 3.2043 no . 4_656
H7 F3 3.3026 no . 4_656
H7 F17 3.1321 no . 4_656
H7 F21 3.4692 no . 4_656
H7 O9 3.0090 no . 1_565
H7 C18 2.9905 no . 1_565
H7 C27 3.4693 no . 1_565
H7 C28 2.9683 no . 1_565
H7 H15 3.2996 no . 1_565
H7 H16 3.0791 no . 1_565
H7 H17 2.2202 no . 1_565
H7 H18 3.3831 no . 1_565
H7 H19 2.0581 no . 1_565
H7 H20 3.5841 no . 1_565
H8 O2 3.5341 no . 5_676
H8 O9 2.8553 no . 1_565
H8 C20 3.1994 no . 1_565
H8 C23 3.3764 no . 1_565
H8 H4 3.3214 no . 1_565
H8 H17 3.0025 no . 1_565
H8 H19 3.4595 no . 1_565
H9 F3 2.9789 no . 7_786
H9 F34 3.5700 no . 7_786
H9 O2 3.0488 no . 5_676
H9 C27 2.8670 no . 5_676
H9 C28 2.7658 no . 5_676
H9 H11 3.2696 no . 2_655
H9 H18 3.4974 no . 5_676
H9 H19 3.2272 no . 5_676
H9 H20 2.0347 no . 5_676
H10 F3 2.9173 no . 7_786
H10 F34 3.4170 no . 7_786
H10 C24 3.5802 no . 6_575
H10 H1 3.0543 no . 7_776
H10 H3 3.3209 no . 6_575
H10 H6 3.0025 no . 6_575
H10 H11 2.8670 no . 2_655
H10 H20 3.3712 no . 5_676
H11 C4 2.9573 no . 2_655
H11 C19 3.5203 no . 5_676
H11 C24 3.3477 no . 5_676
H11 H6 3.3656 no . 5_676
H11 H9 3.2696 no . 2_655
H11 H10 2.8670 no . 2_655
H11 H11 2.3271 no . 2_655
H11 H20 3.4249 no . 5_676
H12 F34 3.0529 no . 7_786
H12 O2 2.9721 no . 5_676
H12 H1 3.0090 no . 7_776
H12 H5 3.2286 no . 7_776
H13 F34 3.0562 no . 7_786
H13 O2 2.7127 no . 5_676
H13 C20 2.9174 no . 1_565
H13 C22 3.0136 no . 1_565
H13 H4 2.6277 no . 1_565
H13 H5 2.7798 no . 1_565
H13 H5 3.5663 no . 7_776
H14 F17 2.8981 no . .
H14 F34 2.8507 no . .
H14 F34 2.9832 no . 7_786
H14 C14 3.4031 no . 7_776
H14 C22 3.5538 no . 1_565
H14 C22 2.9214 no . 7_776
H14 B32 3.2648 no . .
H14 H1 3.0900 no . 7_776
H14 H5 2.9697 no . 1_565
H14 H5 2.1520 no . 7_776
H15 F17 3.2254 no . 4_646
H15 C6 3.4563 no . 4_646
H15 C13 3.0871 no . 4_646
H15 C19 2.9220 no . 4_646
H15 C24 2.8458 no . 4_646
H15 C25 3.2223 no . 4_646
H15 C26 3.5246 no . 4_646
H15 H3 3.3212 no . 4_646
H15 H6 3.2043 no . 4_646
H15 H7 3.2996 no . 1_545
H16 F3 2.4419 no . 4_646
H16 F17 2.4486 no . 4_646
H16 B32 2.8286 no . 4_646
H16 H7 3.0791 no . 1_545
H17 F3 3.2616 no . 4_646
H17 F17 3.3126 no . 4_646
H17 C25 2.9566 no . 1_545
H17 C26 3.3056 no . 1_545
H17 H7 2.2202 no . 1_545
H17 H8 3.0025 no . 1_545
H18 I1 3.5890 no . 5_666
H18 F21 2.7819 no . 3_445
H18 O7 3.2172 no . 5_666
H18 C20 3.5624 no . 5_666
H18 C29 3.5959 no . 5_666
H18 H4 2.7659 no . 5_666
H18 H7 3.3831 no . 1_545
H18 H9 3.4974 no . 5_676
H19 F3 3.2058 no . 4_646
H19 C19 3.3809 no . 1_545
H19 C25 2.6452 no . 1_545
H19 C26 3.3920 no . 1_545
H19 H3 3.3908 no . 1_545
H19 H7 2.0581 no . 1_545
H19 H8 3.4595 no . 1_545
H19 H9 3.2272 no . 5_676
H20 F3 2.8642 no . 3_445
H20 F3 3.5510 no . 4_646
H20 F21 2.9130 no . 3_445
H20 F34 3.5350 no . 3_445
H20 C4 2.9893 no . 5_676
H20 B32 3.3486 no . 3_445
H20 H4 3.5432 no . 5_666
H20 H7 3.5841 no . 1_545
H20 H9 2.0347 no . 5_676
H20 H10 3.3712 no . 5_676
H20 H11 3.4249 no . 5_676

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_1389
_database_code_depnum_ccdc_archive 'CCDC 2049845'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-12-12 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2020-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 F3 O5 S'
_chemical_formula_sum            'C17 H13 F3 O5 S'
_chemical_formula_weight         386.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H13 F3 O5 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   6.49130(10)
_cell_length_b                   9.9728(2)
_cell_length_c                   13.5507(2)
_cell_angle_alpha                98.9150(10)
_cell_angle_beta                 101.8730(10)
_cell_angle_gamma                107.362(2)
_cell_volume                     797.06(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6850
_cell_measurement_temperature    123
_cell_measurement_theta_max      74.2400
_cell_measurement_theta_min      4.7670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.389
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (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_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12166
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.335
_diffrn_reflns_theta_min         3.426
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00 -22.00   0.50    0.06    --  -42.93 116.00  85.00   66
  2  ω    -80.00 -54.00   0.50    0.26    -- -106.00 125.00 -30.00   52
  3  ω    -95.00 -33.00   0.50    0.26    -- -106.00  77.00  30.00  124
  4  ω    -63.00 -34.00   0.50    0.26    -- -106.00  77.00 -30.00   58
  5  ω    -76.00 -47.00   0.50    0.26    -- -106.00  77.00 -60.00   58
  6  ω    -68.00 -33.00   0.50    0.26    -- -106.00  57.00 -60.00   70
  7  ω    -89.00 -26.00   0.50    0.26    -- -106.00  19.00  30.00  126
  8  ω    -96.00 -70.00   0.50    0.26    -- -106.00  -4.00  56.97   52
  9  ω   -124.00 -72.00   0.50    0.26    -- -106.00  57.00  90.00  104
 10  ω   -102.00 -76.00   0.50    0.26    -- -106.00  77.00  90.00   52
 11  ω   -110.00 -71.00   0.50    0.26    -- -106.00 116.00  85.00   78
 12  ω    -98.00 -72.00   0.50    0.26    -- -106.00 125.00 120.00   52
 13  ω    -63.00 -37.00   0.50    0.26    -- -106.00 125.00 150.00   52
 14  ω    -96.00 -63.00   0.50    0.26    -- -106.00 125.00  60.00   66
 15  ω   -114.00 -88.00   0.50    0.26    -- -106.00 125.00 -30.00   52
 16  ω    -98.00 -72.00   0.50    0.26    -- -106.00 125.00 -60.00   52
 17  ω   -102.00 -77.00   0.50    0.26    -- -106.00 125.00 -90.00   50
 18  ω   -119.00 -82.00   0.50    0.26    -- -106.00  77.00 -30.00   74
 19  ω    -92.00 -30.00   0.50    0.26    -- -106.00  37.00 -90.00  124
 20  ω    -85.00 -33.00   0.50    0.26    -- -106.00  77.00-180.00  104
 21  ω    -91.00 -66.00   0.50    0.26    -- -106.00  57.00 -90.00   50
 22  ω   -109.00 -82.00   0.50    0.26    -- -106.00  57.00 -60.00   54
 23  ω   -120.00 -94.00   0.50    0.26    -- -106.00  37.00 -90.00   52
 24  ω   -118.00 -75.00   0.50    0.26    -- -106.00 -19.00 -60.00   86
 25  ω   -102.00 -77.00   0.50    0.26    -- -106.00 -77.00-150.00   50
 26  ω   -105.00 -79.00   0.50    0.06    --  -42.93-163.00-152.00   52
 27  ω   -127.00-102.00   0.50    0.26    -- -106.00-163.00-152.00   50
 28  ω   -167.00-129.00   0.50    0.26    -- -106.00 -99.00-180.00   76
 29  ω   -161.00-105.00   0.50    0.26    -- -106.00 -99.00-120.00  112
 30  ω   -151.00-126.00   0.50    0.26    -- -106.00-116.00  -2.00   50
 31  ω   -158.00-133.00   0.50    0.26    -- -106.00 -93.00  70.01   50
 32  ω   -122.00 -83.00   0.50    0.26    -- -106.00 -99.00 120.00   78
 33  ω   -107.00 -81.00   0.50    0.26    -- -106.00 -93.00  70.01   52
 34  ω   -133.00 -73.00   0.50    0.26    -- -106.00-125.00  90.00  120
 35  ω   -139.00 -89.00   0.50    0.26    -- -106.00 -37.00  30.00  100
 36  ω   -144.00-112.00   0.50    0.26    -- -106.00 -37.00 120.00   64
 37  ω   -147.00-122.00   0.50    0.26    -- -106.00  -4.00  56.97   50
 38  ω   -174.00-125.00   0.50    0.26    -- -106.00 -57.00 120.00   98
 39  ω   -176.00 -95.00   0.50    0.26    -- -106.00 -37.00  90.00  162
 40  ω   -131.00-104.00   0.50    0.26    -- -106.00  77.00 -60.00   54
 41  ω   -127.00 -66.00   0.50    0.26    -- -106.00  47.00-132.05  122
 42  ω   -117.00 -40.00   0.50    0.26    -- -106.00 125.00  30.00  154
 43  ω   -115.00 -80.00   0.50    0.26    -- -106.00 125.00 150.00   70
 44  ω   -117.00 -86.00   0.50    0.26    -- -106.00 125.00  90.00   62
 45  ω   -129.00-104.00   0.50    0.26    -- -106.00 141.00 132.92   50
 46  ω   -124.00 -99.00   0.50    0.26    -- -106.00  80.00  47.97   50
 47  ω   -120.00 -75.00   0.50    0.06    --  -42.93 163.00-125.00   90
 48  ω     72.00 117.00   0.50    0.06    --   42.93 125.00 120.00   90
 49  ω     89.00 114.00   0.50    0.26    --   76.50 116.00  85.00   50
 50  ω     86.00 117.00   0.50    0.06    --   42.93 125.00  30.00   62
 51  ω     78.00 103.00   0.50    0.06    --   42.93 125.00   0.00   50
 52  ω     62.00 100.00   0.50    0.06    --   42.93 163.00-125.00   76
 53  ω     74.00  99.00   0.50    0.26    --   76.50 163.00-125.00   50
 54  ω     71.00 115.00   0.50    0.06    --   42.93 125.00-180.00   88
 55  ω     71.00 117.00   0.50    0.06    --   42.93 125.00-150.00   92
 56  ω     19.00 116.00   0.50    0.06    --   42.93  77.00-180.00  194
 57  ω     34.00  89.00   0.50    0.06    --   42.93-116.00  -2.00  110
 58  ω     34.00  59.00   0.50    0.26    --   76.50-116.00  -2.00   50
 59  ω     75.00 100.00   0.50    0.06    --   42.93-163.00-152.00   50
 60  ω     62.00  87.00   0.50    0.26    --   76.50-163.00-152.00   50
 61  ω   -135.00-109.00   0.50    0.26    -- -106.00 163.00-125.00   52
 62  ω   -177.00 -99.00   0.50    0.26    -- -106.00 -37.00 150.00  156
 63  ω   -166.00-141.00   0.50    0.26    -- -106.00-125.00 150.00   50
 64  ω   -167.00-126.00   0.50    0.26    -- -106.00 -77.00-150.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0051498000
_diffrn_orient_matrix_UB_12      -0.1186819000
_diffrn_orient_matrix_UB_13      -0.0889806000
_diffrn_orient_matrix_UB_21      -0.0413147000
_diffrn_orient_matrix_UB_22      0.0930322000
_diffrn_orient_matrix_UB_23      -0.0776016000
_diffrn_orient_matrix_UB_31      0.2546611000
_diffrn_orient_matrix_UB_32      0.0702891000
_diffrn_orient_matrix_UB_33      0.0179491000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2910
_reflns_number_total             3220
_reflns_odcompleteness_completeness 98.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (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         0.442
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.093
_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)+(0.1104P)²+0.0967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1573
_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:
 C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00H(H00H), C00J(H00J), C00L(H00L), C00M(H00M),
 C00O(H00O)
2.d Idealised Me refined as rotating group:
 C00Q(H00C,H00G,H00I)
;
_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
S001 S 0.41621(6) -0.06918(4) 0.21348(3) 0.02256(19) Uani 1 1 d . . . . .
F002 F 0.4806(2) 0.56254(15) 0.24600(13) 0.0426(4) Uani 1 1 d . . . . .
O003 O 1.0148(2) 0.13321(15) 0.47377(12) 0.0291(3) Uani 1 1 d . . . . .
O004 O 1.3380(2) 0.28140(15) 0.47098(12) 0.0298(3) Uani 1 1 d . . . . .
O005 O 0.2945(2) -0.13350(14) 0.28109(12) 0.0291(3) Uani 1 1 d . . . . .
F006 F 0.7923(2) 0.73535(14) 0.28983(15) 0.0516(4) Uani 1 1 d . . . . .
O007 O 0.65346(19) 0.04143(13) 0.28150(10) 0.0225(3) Uani 1 1 d . . . . .
O008 O 0.4692(2) -0.15579(15) 0.13541(12) 0.0322(3) Uani 1 1 d . . . . .
F009 F 0.6995(3) 0.5764(2) 0.14802(12) 0.0609(5) Uani 1 1 d . . . . .
C00A C 0.7860(3) 0.29137(18) 0.36563(14) 0.0205(4) Uani 1 1 d . . . . .
C00B C 1.0195(3) 0.34304(19) 0.40260(14) 0.0212(4) Uani 1 1 d . . . . .
C00C C 0.8066(3) 0.50542(19) 0.30242(15) 0.0229(4) Uani 1 1 d . . . . .
C00D C 0.6783(3) 0.37450(19) 0.31617(15) 0.0220(4) Uani 1 1 d . . . . .
H00D H 0.519514 0.341855 0.292316 0.026 Uiso 1 1 calc R . . . .
C00E C 1.1465(3) 0.47437(19) 0.38794(15) 0.0236(4) Uani 1 1 d . . . . .
H00E H 1.305104 0.508474 0.413208 0.028 Uiso 1 1 calc R . . . .
C00F C 0.6603(3) 0.14276(18) 0.37469(15) 0.0214(4) Uani 1 1 d . . . . .
H00F H 0.504897 0.135264 0.377989 0.026 Uiso 1 1 calc R . . . .
C00G C 1.1382(3) 0.25353(19) 0.45263(15) 0.0236(4) Uani 1 1 d . . . . .
C00H C 0.3730(3) 0.1125(2) 0.08704(16) 0.0267(4) Uani 1 1 d . . . . .
H00H H 0.490513 0.091598 0.063438 0.032 Uiso 1 1 calc R . . . .
C00I C 0.2873(3) 0.04442(19) 0.15966(15) 0.0228(4) Uani 1 1 d . . . . .
C00J C 1.0404(3) 0.55498(19) 0.33630(16) 0.0247(4) Uani 1 1 d . . . . .
H00J H 1.125756 0.643259 0.323992 0.030 Uiso 1 1 calc R . . . .
C00K C 0.1112(3) 0.2421(2) 0.08450(16) 0.0274(4) Uani 1 1 d . . . . .
C00L C 0.1104(3) 0.0702(2) 0.19302(15) 0.0255(4) Uani 1 1 d . . . . .
H00L H 0.049312 0.020709 0.240573 0.031 Uiso 1 1 calc R . . . .
C00M C 0.2849(3) 0.2106(2) 0.04990(16) 0.0281(4) Uani 1 1 d . . . . .
H00M H 0.342455 0.257373 0.000416 0.034 Uiso 1 1 calc R . . . .
C00N C 0.6942(3) 0.5954(2) 0.24638(16) 0.0267(4) Uani 1 1 d . . . . .
C00O C 0.0260(3) 0.1698(2) 0.15501(16) 0.0285(4) Uani 1 1 d . . . . .
H00O H -0.093433 0.189176 0.177764 0.034 Uiso 1 1 calc R . . . .
C00P C 0.7792(3) 0.1046(2) 0.46761(16) 0.0255(4) Uani 1 1 d . . . . .
H00A H 0.765055 0.161008 0.531171 0.031 Uiso 1 1 calc R . . . .
H00B H 0.706477 0.000885 0.464378 0.031 Uiso 1 1 calc R . . . .
C00Q C 0.0228(4) 0.3537(3) 0.04693(19) 0.0368(5) Uani 1 1 d . . . . .
H00C H 0.122411 0.450254 0.086688 0.055 Uiso 1 1 calc GR . . . .
H00G H -0.127669 0.337532 0.056376 0.055 Uiso 1 1 calc GR . . . .
H00I H 0.016082 0.345864 -0.026732 0.055 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
S001 O005 1.4325(14) . ?
S001 O007 1.5891(13) . ?
S001 O008 1.4240(15) . ?
S001 C00I 1.7570(18) . ?
F002 C00N 1.325(2) . ?
O003 C00G 1.338(2) . ?
O003 C00P 1.452(2) . ?
O004 C00G 1.205(2) . ?
F006 C00N 1.327(2) . ?
O007 C00F 1.474(2) . ?
F009 C00N 1.326(3) . ?
C00A C00B 1.398(2) . ?
C00A C00D 1.397(3) . ?
C00A C00F 1.501(2) . ?
C00B C00E 1.392(2) . ?
C00B C00G 1.494(2) . ?
C00C C00D 1.387(2) . ?
C00C C00J 1.398(3) . ?
C00C C00N 1.513(2) . ?
C00E C00J 1.385(3) . ?
C00F C00P 1.500(3) . ?
C00H C00I 1.395(3) . ?
C00H C00M 1.380(3) . ?
C00I C00L 1.394(2) . ?
C00K C00M 1.405(3) . ?
C00K C00O 1.390(3) . ?
C00K C00Q 1.504(3) . ?
C00L C00O 1.386(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
O005 S001 O007 108.71(8) . . ?
O005 S001 C00I 109.04(8) . . ?
O007 S001 C00I 102.50(7) . . ?
O008 S001 O005 120.79(9) . . ?
O008 S001 O007 103.80(7) . . ?
O008 S001 C00I 110.34(9) . . ?
C00G O003 C00P 121.03(14) . . ?
C00F O007 S001 117.99(10) . . ?
C00B C00A C00F 118.21(15) . . ?
C00D C00A C00B 119.64(16) . . ?
C00D C00A C00F 122.03(15) . . ?
C00A C00B C00G 120.39(16) . . ?
C00E C00B C00A 120.81(16) . . ?
C00E C00B C00G 118.69(15) . . ?
C00D C00C C00J 121.43(17) . . ?
C00D C00C C00N 120.00(16) . . ?
C00J C00C C00N 118.54(16) . . ?
C00C C00D C00A 118.98(16) . . ?
C00J C00E C00B 119.61(16) . . ?
O007 C00F C00A 106.58(13) . . ?
O007 C00F C00P 107.83(14) . . ?
C00P C00F C00A 111.52(15) . . ?
O003 C00G C00B 118.13(15) . . ?
O004 C00G O003 118.59(16) . . ?
O004 C00G C00B 123.21(17) . . ?
C00M C00H C00I 119.19(16) . . ?
C00H C00I S001 118.42(13) . . ?
C00L C00I S001 120.14(15) . . ?
C00L C00I C00H 121.38(17) . . ?
C00E C00J C00C 119.47(16) . . ?
C00M C00K C00Q 120.33(18) . . ?
C00O C00K C00M 118.65(18) . . ?
C00O C00K C00Q 121.02(17) . . ?
C00O C00L C00I 118.25(17) . . ?
C00H C00M C00K 120.70(18) . . ?
F002 C00N F006 106.65(16) . . ?
F002 C00N F009 106.59(18) . . ?
F002 C00N C00C 112.46(15) . . ?
F006 C00N C00C 111.78(17) . . ?
F009 C00N F006 107.56(17) . . ?
F009 C00N C00C 111.48(15) . . ?
C00L C00O C00K 121.78(16) . . ?
O003 C00P C00F 112.24(15) . . ?

_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 3.630
_oxdiff_exptl_absorpt_empirical_full_min 0.309
####################################################################### 
# 
# 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_xcalibur_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2044652'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-11-14 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H21 B F4 I N O4'
_chemical_formula_moiety         'C18 H21 B F4 I N O4'
_chemical_formula_weight         529.08
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.2481
_cell_length_b                   8.6049
_cell_length_c                   16.0914
_cell_angle_alpha                92.5940
_cell_angle_beta                 94.6460
_cell_angle_gamma                114.1890
_cell_volume                     1034.5014
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6314
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      29.25
_cell_measurement_temperature    213
#------------------------------------------------------------------------------
_exptl_crystal_description       nONE
_exptl_crystal_colour            nONE
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524.00
_exptl_absorpt_coefficient_mu    1.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_T_max  1.000

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      213
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            12244
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_theta_max         30.87
_diffrn_reflns_theta_min         2.549
_diffrn_reflns_theta_full        27.05
_diffrn_measured_fraction_theta_max 0.783
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5100
_reflns_number_gt                4486
_reflns_threshold_expression     F>2.0σ(F)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F > 2.0 sigma(F).
    The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are 
    based on F, with F set to zero for negative F. The threshold expression of
    F > 2.0 sigma(F) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0391
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4486
_refine_ls_number_parameters     283
_refine_ls_goodness_of_fit_ref   1.530
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     'w = 1/σ²(Fo)'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         1.320
_refine_diff_density_min         -0.686
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.73856(3) 0.57034(3) 0.412650(10) 0.02961(6) Uani 1 2 d . . .
F4 F 1.0715(4) 0.1502(5) 0.1317(2) 0.0926(12) Uani 1 2 d . . .
F22 F 1.2087(5) -0.0248(5) 0.1581(3) 0.1146(15) Uani 1 2 d . . .
F23 F 1.3313(5) 0.1901(7) 0.0867(3) 0.1391(19) Uani 1 2 d . . .
F31 F 1.3211(5) 0.2314(6) 0.2215(3) 0.1328(17) Uani 1 2 d . . .
O3 O 0.6413(3) 0.2931(3) 0.39057(16) 0.0376(7) Uani 1 2 d . . .
O7 O 0.4324(4) 0.3016(4) 0.4645(2) 0.0549(9) Uani 1 2 d . . .
O9 O 0.7448(5) 0.8377(4) 0.2971(2) 0.0853(12) Uani 1 2 d . . .
O10 O 0.8861(3) 0.8355(3) 0.41997(16) 0.0377(7) Uani 1 2 d . . .
N27 N 0.7310(4) 0.3940(4) 0.12627(19) 0.0357(8) Uani 1 2 d . . .
C5 C 0.7834(7) 0.6920(6) 0.1010(3) 0.0642(16) Uani 1 2 d . . .
C6 C 0.4892(5) 0.2206(5) 0.4214(2) 0.0365(10) Uani 1 2 d . . .
C8 C 0.9439(4) 0.5570(4) 0.3483(2) 0.0284(8) Uani 1 2 d . . .
C11 C 1.0604(5) 0.4939(5) 0.2288(3) 0.0397(10) Uani 1 2 d . . .
C12 C 0.8494(5) 0.9134(5) 0.3573(3) 0.0410(11) Uani 1 2 d . . .
C13 C 1.2274(5) 0.5449(5) 0.2747(3) 0.0434(11) Uani 1 2 d . . .
C14 C 0.9562(6) 1.1028(5) 0.3684(3) 0.0495(12) Uani 1 2 d . . .
C15 C 0.7553(5) 0.5162(5) 0.0710(3) 0.0424(11) Uani 1 2 d . . .
C16 C 1.1079(4) 0.6073(5) 0.3953(2) 0.0345(10) Uani 1 2 d . . .
C17 C 0.9154(4) 0.4981(5) 0.2639(2) 0.0308(9) Uani 1 2 d . . .
C18 C 0.7135(5) 0.1925(6) 0.0186(3) 0.0473(12) Uani 1 2 d . . .
C19 C 0.7086(5) 0.2331(5) 0.1020(3) 0.0395(11) Uani 1 2 d . . .
C20 C 0.7318(4) 0.4422(6) 0.2162(2) 0.0394(10) Uani 1 2 d . . .
C21 C 1.2491(5) 0.5993(5) 0.3578(3) 0.0415(11) Uani 1 2 d . . .
C24 C 0.7347(6) 0.3103(6) -0.0382(3) 0.0541(13) Uani 1 2 d . . .
C26 C 0.3919(6) 0.0318(5) 0.3982(3) 0.0568(13) Uani 1 2 d . . .
C28 C 0.7538(6) 0.4707(6) -0.0118(3) 0.0512(13) Uani 1 2 d . . .
C29 C 0.6793(6) 0.1045(6) 0.1641(3) 0.0554(14) Uani 1 2 d . . .
B25 B 1.2283(6) 0.1394(7) 0.1495(4) 0.0552(16) Uani 1 2 d . . .
H1 H 1.04537 0.45447 0.1727 0.0477 Uiso 1 2 calc R . .
H2 H 1.32341 0.54285 0.24883 0.0521 Uiso 1 2 calc R . .
H3 H 1.12198 0.64611 0.45149 0.0414 Uiso 1 2 calc R . .
H4 H 0.70268 0.08399 0.00092 0.0556 Uiso 1 2 calc R . .
H5 H 1.3599 0.63205 0.38871 0.0501 Uiso 1 2 calc R . .
H6 H 0.73543 0.28218 -0.09463 0.0618 Uiso 1 2 calc R . .
H7 H 0.76681 0.55077 -0.0506 0.0606 Uiso 1 2 calc R . .
H8 H 0.87455 0.73239 0.14771 0.0788 Uiso 1 2 calc R . .
H9 H 0.82092 0.76594 0.0568 0.0789 Uiso 1 2 calc R . .
H10 H 0.6745 0.69176 0.11809 0.0789 Uiso 1 2 calc R . .
H11 H 1.03921 1.13219 0.41804 0.0586 Uiso 1 2 calc R . .
H12 H 1.02065 1.13988 0.32076 0.0586 Uiso 1 2 calc R . .
H13 H 0.87702 1.15828 0.37362 0.0585 Uiso 1 2 calc R . .
H14 H 0.69465 0.53543 0.21943 0.0470 Uiso 1 2 calc R . .
H15 H 0.64583 0.34399 0.23969 0.0470 Uiso 1 2 calc R . .
H16 H 0.47289 -0.02115 0.40875 0.0643 Uiso 1 2 calc R . .
H17 H 0.29298 -0.01672 0.43059 0.0644 Uiso 1 2 calc R . .
H18 H 0.34849 0.01246 0.33975 0.0643 Uiso 1 2 calc R . .
H19 H 0.56538 0.07707 0.18453 0.0675 Uiso 1 2 calc R . .
H20 H 0.68154 0.00286 0.13816 0.0676 Uiso 1 2 calc R . .
H21 H 0.77221 0.15061 0.20992 0.0676 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
I1 O3 2.184(3) yes .
I1 O10 2.092(2) yes .
I1 C8 2.095(4) yes .
F4 B25 1.343(7) yes .
F22 B25 1.370(8) yes .
F23 B25 1.344(7) yes .
F31 B25 1.354(7) yes .
O3 C6 1.303(4) yes .
O7 C6 1.209(6) yes .
O9 C12 1.207(5) yes .
O10 C12 1.317(5) yes .
N27 C15 1.370(6) yes .
N27 C19 1.354(6) yes .
N27 C20 1.486(5) yes .
C5 C15 1.484(7) yes .
C6 C26 1.500(5) yes .
C8 C16 1.384(5) yes .
C8 C17 1.394(5) yes .
C11 C13 1.395(5) yes .
C11 C17 1.376(6) yes .
C12 C14 1.495(5) yes .
C13 C21 1.368(6) yes .
C15 C28 1.370(6) yes .
C16 C21 1.380(6) yes .
C17 C20 1.515(5) yes .
C18 C19 1.380(6) yes .
C18 C24 1.362(7) yes .
C19 C29 1.483(7) yes .
C24 C28 1.367(8) yes .
C5 H8 0.960 no .
C5 H9 0.960 no .
C5 H10 0.960 no .
C11 H1 0.930 no .
C13 H2 0.930 no .
C14 H11 0.960 no .
C14 H12 0.960 no .
C14 H13 0.960 no .
C16 H3 0.930 no .
C18 H4 0.930 no .
C20 H14 0.970 no .
C20 H15 0.970 no .
C21 H5 0.930 no .
C24 H6 0.930 no .
C26 H16 0.960 no .
C26 H17 0.960 no .
C26 H18 0.960 no .
C28 H7 0.930 no .
C29 H19 0.960 no .
C29 H20 0.960 no .
C29 H21 0.960 no .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3 I1 O10 165.78(11) yes . .
O3 I1 C8 80.33(11) yes . .
O10 I1 C8 85.48(12) yes . .
I1 O3 C6 109.0(3) yes . .
I1 O10 C12 115.7(2) yes . .
C15 N27 C19 122.5(3) yes . .
C15 N27 C20 118.2(4) yes . .
C19 N27 C20 119.3(3) yes . .
O3 C6 O7 121.7(3) yes . .
O3 C6 C26 114.6(4) yes . .
O7 C6 C26 123.6(3) yes . .
I1 C8 C16 115.6(3) yes . .
I1 C8 C17 121.9(2) yes . .
C16 C8 C17 122.5(4) yes . .
C13 C11 C17 122.2(4) yes . .
O9 C12 O10 122.9(4) yes . .
O9 C12 C14 124.6(4) yes . .
O10 C12 C14 112.4(3) yes . .
C11 C13 C21 119.5(4) yes . .
N27 C15 C5 120.5(4) yes . .
N27 C15 C28 117.8(4) yes . .
C5 C15 C28 121.7(4) yes . .
C8 C16 C21 119.1(3) yes . .
C8 C17 C11 116.5(3) yes . .
C8 C17 C20 119.9(3) yes . .
C11 C17 C20 123.6(3) yes . .
C19 C18 C24 120.6(5) yes . .
N27 C19 C18 118.4(4) yes . .
N27 C19 C29 120.4(4) yes . .
C18 C19 C29 121.3(4) yes . .
N27 C20 C17 111.8(3) yes . .
C13 C21 C16 120.2(3) yes . .
C18 C24 C28 119.5(4) yes . .
C15 C28 C24 121.1(5) yes . .
F4 B25 F22 112.8(4) yes . .
F4 B25 F23 111.0(5) yes . .
F4 B25 F31 113.1(6) yes . .
F22 B25 F23 104.6(6) yes . .
F22 B25 F31 105.9(5) yes . .
F23 B25 F31 109.0(4) yes . .
C15 C5 H8 108.910 no . .
C15 C5 H9 109.482 no . .
C15 C5 H10 110.104 no . .
H8 C5 H9 109.445 no . .
H8 C5 H10 109.442 no . .
H9 C5 H10 109.442 no . .
C13 C11 H1 119.351 no . .
C17 C11 H1 118.453 no . .
C11 C13 H2 120.052 no . .
C21 C13 H2 120.421 no . .
C12 C14 H11 109.566 no . .
C12 C14 H12 109.613 no . .
C12 C14 H13 109.320 no . .
H11 C14 H12 109.445 no . .
H11 C14 H13 109.441 no . .
H12 C14 H13 109.442 no . .
C8 C16 H3 120.100 no . .
C21 C16 H3 120.818 no . .
C19 C18 H4 119.744 no . .
C24 C18 H4 119.626 no . .
N27 C20 H14 107.689 no . .
N27 C20 H15 108.011 no . .
C17 C20 H14 109.558 no . .
C17 C20 H15 110.217 no . .
H14 C20 H15 109.450 no . .
C13 C21 H5 119.706 no . .
C16 C21 H5 120.047 no . .
C18 C24 H6 120.630 no . .
C28 C24 H6 119.871 no . .
C6 C26 H16 109.088 no . .
C6 C26 H17 110.226 no . .
C6 C26 H18 109.180 no . .
H16 C26 H17 109.441 no . .
H16 C26 H18 109.447 no . .
H17 C26 H18 109.443 no . .
C15 C28 H7 119.218 no . .
C24 C28 H7 119.635 no . .
C19 C29 H19 109.614 no . .
C19 C29 H20 109.576 no . .
C19 C29 H21 109.309 no . .
H19 C29 H20 109.438 no . .
H19 C29 H21 109.443 no . .
H20 C29 H21 109.448 no . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 I1 C8 C16 -111.0(2) no . . . .
O3 I1 C8 C17 67.8(2) no . . . .
C8 I1 O3 C6 -179.05(18) no . . . .
O10 I1 C8 C16 68.0(2) no . . . .
O10 I1 C8 C17 -113.2(2) no . . . .
C8 I1 O10 C12 89.5(2) no . . . .
I1 O3 C6 O7 -9.0(4) no . . . .
I1 O3 C6 C26 170.2(2) no . . . .
I1 O10 C12 O9 -3.8(5) no . . . .
I1 O10 C12 C14 178.2(2) no . . . .
C15 N27 C19 C18 1.1(5) no . . . .
C15 N27 C19 C29 -178.8(3) no . . . .
C19 N27 C15 C5 -178.6(3) no . . . .
C19 N27 C15 C28 1.0(5) no . . . .
C15 N27 C20 C17 -94.1(4) no . . . .
C20 N27 C15 C5 0.6(5) no . . . .
C20 N27 C15 C28 -179.8(3) no . . . .
C19 N27 C20 C17 85.2(4) no . . . .
C20 N27 C19 C18 -178.2(3) no . . . .
C20 N27 C19 C29 2.0(5) no . . . .
I1 C8 C16 C21 178.9(2) no . . . .
I1 C8 C17 C11 -179.4(2) no . . . .
I1 C8 C17 C20 0.2(5) no . . . .
C16 C8 C17 C11 -0.7(5) no . . . .
C16 C8 C17 C20 179.0(3) no . . . .
C17 C8 C16 C21 0.0(5) no . . . .
C13 C11 C17 C8 0.3(6) no . . . .
C13 C11 C17 C20 -179.4(3) no . . . .
C17 C11 C13 C21 0.8(6) no . . . .
C11 C13 C21 C16 -1.4(6) no . . . .
N27 C15 C28 C24 -2.1(6) no . . . .
C5 C15 C28 C24 177.4(4) no . . . .
C8 C16 C21 C13 1.0(6) no . . . .
C8 C17 C20 N27 176.5(3) no . . . .
C11 C17 C20 N27 -3.9(6) no . . . .
C19 C18 C24 C28 0.9(6) no . . . .
C24 C18 C19 N27 -2.0(6) no . . . .
C24 C18 C19 C29 177.8(3) no . . . .
C18 C24 C28 C15 1.2(6) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
I1 O7 2.855(3) no . .
I1 O9 3.010(4) no . .
I1 C20 3.289(4) no . .
O3 C17 3.191(4) no . .
O3 C20 3.155(5) no . .
O9 C5 3.430(7) no . .
O9 C8 3.524(6) no . .
O9 C20 3.545(6) no . .
O10 C16 3.216(5) no . .
N27 C11 2.842(5) no . .
N27 C24 2.717(6) no . .
C5 C17 3.502(7) no . .
C5 C20 2.824(7) no . .
C8 C12 3.460(6) no . .
C8 C13 2.742(6) no . .
C11 C15 3.496(6) no . .
C11 C16 2.751(5) no . .
C11 C19 3.303(5) no . .
C11 C29 3.566(5) no . .
C15 C17 3.309(6) no . .
C15 C18 2.746(7) no . .
C17 C19 3.233(5) no . .
C17 C21 2.803(5) no . .
C17 C29 3.382(5) no . .
C19 C28 2.738(7) no . .
C20 C29 2.832(7) no . .
I1 O7 2.940(4) no . 2_666
F4 C11 3.320(6) no . .
F4 C18 3.498(6) no . .
F4 C19 3.353(6) no . .
F4 C29 3.185(6) no . .
F22 C5 3.370(6) no . 1_545
F22 C18 3.356(7) no . 2_755
F22 C24 3.261(7) no . 2_755
F22 C29 3.564(6) no . 1_655
F23 N27 3.028(4) no . 1_655
F23 C5 3.414(7) no . 2_765
F23 C15 3.512(5) no . 1_655
F23 C18 3.413(7) no . 1_655
F23 C18 3.500(8) no . 2_755
F23 C19 2.967(6) no . 1_655
F23 C20 3.544(5) no . 1_655
F23 C28 3.511(8) no . 2_765
F23 C29 3.400(7) no . 1_655
F31 O3 3.495(5) no . 1_655
F31 N27 3.591(5) no . 1_655
F31 C6 3.419(6) no . 1_655
F31 C13 3.196(7) no . .
F31 C20 3.131(5) no . 1_655
F31 C26 3.516(7) no . 1_655
O3 F31 3.495(5) no . 1_455
O7 I1 2.940(4) no . 2_666
O7 O7 3.245(4) no . 2_666
O7 O10 3.194(4) no . 2_666
O7 C21 3.540(5) no . 2_766
O9 C29 3.379(7) no . 1_565
O10 O7 3.194(4) no . 2_666
O10 O10 3.518(3) no . 2_776
O10 C14 3.482(5) no . 2_776
N27 F23 3.028(4) no . 1_455
N27 F31 3.591(5) no . 1_455
C5 F22 3.370(6) no . 1_565
C5 F23 3.414(7) no . 2_765
C6 F31 3.419(6) no . 1_455
C11 F4 3.320(6) no . .
C13 F31 3.196(7) no . .
C14 O10 3.482(5) no . 2_776
C15 F23 3.512(5) no . 1_455
C16 C26 3.433(5) no . 1_665
C18 F4 3.498(6) no . .
C18 F22 3.356(7) no . 2_755
C18 F23 3.413(7) no . 1_455
C18 F23 3.500(8) no . 2_755
C19 F4 3.353(6) no . .
C19 F23 2.967(6) no . 1_455
C20 F23 3.544(5) no . 1_455
C20 F31 3.131(5) no . 1_455
C21 O7 3.540(5) no . 2_766
C21 C26 3.424(6) no . 1_665
C24 F22 3.261(7) no . 2_755
C26 F31 3.516(7) no . 1_455
C26 C16 3.433(5) no . 1_445
C26 C21 3.424(6) no . 1_445
C28 F23 3.511(8) no . 2_765
C29 F4 3.185(6) no . .
C29 F22 3.564(6) no . 1_455
C29 F23 3.400(7) no . 1_455
C29 O9 3.379(7) no . 1_545
I1 H3 2.9615 no . .
I1 H14 3.0874 no . .
I1 H15 3.1731 no . .
O3 H14 3.4769 no . .
O3 H15 2.4870 no . .
O3 H16 2.5273 no . .
O3 H17 3.1552 no . .
O3 H18 2.6562 no . .
O3 H21 3.5200 no . .
O7 H16 3.0350 no . .
O7 H17 2.5109 no . .
O7 H18 2.9341 no . .
O9 H8 2.9597 no . .
O9 H10 3.0026 no . .
O9 H11 3.1387 no . .
O9 H12 2.6468 no . .
O9 H13 2.7065 no . .
O9 H14 2.6905 no . .
O10 H3 3.0347 no . .
O10 H11 2.3420 no . .
O10 H12 2.9873 no . .
O10 H13 2.9371 no . .
N27 H1 2.4692 no . .
N27 H4 3.1882 no . .
N27 H7 3.1882 no . .
N27 H8 2.6490 no . .
N27 H9 3.2490 no . .
N27 H10 2.7927 no . .
N27 H19 2.7511 no . .
N27 H20 3.2367 no . .
N27 H21 2.6604 no . .
C5 H7 2.6432 no . .
C5 H14 2.3734 no . .
C6 H15 3.3346 no . .
C8 H1 3.1973 no . .
C8 H5 3.2248 no . .
C8 H14 2.7422 no . .
C8 H15 2.7888 no . .
C11 H5 3.2284 no . .
C11 H8 3.2805 no . .
C11 H14 3.1730 no . .
C11 H15 3.1451 no . .
C11 H21 2.9183 no . .
C12 H14 3.5523 no . .
C13 H3 3.2251 no . .
C15 H1 3.0284 no . .
C15 H6 3.2188 no . .
C15 H14 2.4914 no . .
C15 H15 3.1692 no . .
C16 H2 3.2243 no . .
C17 H2 3.2572 no . .
C17 H3 3.2673 no . .
C17 H8 2.9101 no . .
C17 H21 2.7923 no . .
C18 H1 3.4731 no . .
C18 H7 3.1958 no . .
C18 H19 3.0633 no . .
C18 H20 2.5397 no . .
C18 H21 3.1380 no . .
C19 H1 2.7557 no . .
C19 H6 3.2243 no . .
C19 H14 3.1918 no . .
C19 H15 2.5470 no . .
C20 H1 2.6955 no . .
C20 H8 2.6243 no . .
C20 H10 2.8890 no . .
C20 H19 2.8675 no . .
C20 H21 2.6616 no . .
C21 H1 3.2223 no . .
C28 H4 3.1963 no . .
C28 H8 3.1433 no . .
C28 H9 2.5449 no . .
C28 H10 3.0496 no . .
C29 H1 3.2631 no . .
C29 H4 2.6515 no . .
C29 H15 2.4687 no . .
H1 H2 2.3172 no . .
H1 H8 3.2592 no . .
H1 H14 3.3727 no . .
H1 H15 3.3206 no . .
H1 H21 2.7936 no . .
H2 H5 2.3001 no . .
H3 H5 2.3218 no . .
H4 H6 2.2962 no . .
H4 H19 3.2432 no . .
H4 H20 2.3445 no . .
H4 H21 3.3484 no . .
H6 H7 2.2896 no . .
H7 H8 3.3714 no . .
H7 H9 2.3499 no . .
H7 H10 3.1959 no . .
H8 H14 2.1908 no . .
H8 H15 3.5571 no . .
H9 H14 3.3295 no . .
H10 H14 2.1987 no . .
H10 H15 3.5868 no . .
H15 H18 3.4738 no . .
H15 H19 2.2304 no . .
H15 H20 3.4242 no . .
H15 H21 2.3485 no . .
H18 H19 3.1277 no . .
I1 H3 3.3598 no . 2_766
I1 H5 3.3716 no . 1_455
I1 H11 3.4712 no . 2_776
F4 H1 2.7687 no . .
F4 H2 3.5101 no . .
F4 H4 3.3826 no . .
F4 H7 2.8064 no . 2_765
F4 H8 3.3162 no . 1_545
F4 H9 3.2083 no . 1_545
F4 H9 3.2585 no . 2_765
F4 H12 3.1048 no . 1_545
F4 H20 2.9477 no . .
F4 H21 2.8616 no . .
F22 H4 2.7991 no . 2_755
F22 H6 2.6212 no . 2_755
F22 H8 2.6763 no . 1_545
F22 H9 3.2092 no . 1_545
F22 H18 3.0067 no . 1_655
F22 H19 2.6938 no . 1_655
F23 H4 2.5932 no . 2_755
F23 H7 2.7359 no . 2_765
F23 H9 2.6559 no . 2_765
F23 H10 3.4954 no . 2_765
F23 H15 3.2241 no . 1_655
F23 H19 2.8869 no . 1_655
F31 H1 3.5916 no . .
F31 H2 2.6885 no . .
F31 H7 3.5864 no . 2_765
F31 H12 2.9097 no . 1_545
F31 H14 3.1240 no . 1_655
F31 H15 2.4330 no . 1_655
F31 H18 2.7968 no . 1_655
F31 H19 2.9141 no . 1_655
O3 H3 2.9638 no . 2_766
O3 H5 3.5823 no . 2_766
O3 H13 2.6658 no . 1_545
O7 H5 3.3939 no . 1_455
O7 H5 2.6949 no . 2_766
O7 H11 2.9727 no . 1_445
O7 H16 3.5111 no . 2_656
O9 H2 3.3581 no . 1_455
O9 H5 3.4311 no . 1_455
O9 H16 3.5241 no . 1_565
O9 H19 3.4806 no . 1_565
O9 H20 3.0909 no . 1_565
O9 H21 3.0271 no . 1_565
O10 H11 2.6048 no . 2_776
O10 H17 3.0491 no . 1_665
O10 H17 3.5386 no . 2_666
C5 H20 3.1622 no . 1_565
C6 H3 3.3899 no . 2_766
C6 H5 3.1982 no . 2_766
C6 H11 3.4652 no . 1_445
C6 H13 3.5887 no . 1_545
C6 H16 3.3518 no . 2_656
C8 H13 3.2949 no . 1_545
C11 H6 3.0848 no . 2_765
C11 H7 3.3781 no . 2_765
C11 H12 3.3533 no . 1_545
C12 H16 3.5290 no . 1_565
C12 H17 3.5454 no . 1_665
C12 H21 3.3849 no . 1_565
C13 H6 3.2970 no . 2_765
C13 H12 3.3420 no . 1_545
C14 H17 3.4294 no . 1_665
C14 H21 2.9926 no . 1_565
C16 H3 3.5043 no . 2_766
C16 H13 3.5241 no . 1_545
C16 H16 3.3579 no . 1_665
C16 H17 2.9603 no . 1_665
C16 H18 3.4339 no . 1_665
C17 H13 3.4012 no . 1_545
C18 H4 3.2568 no . 2_655
C19 H4 3.5765 no . 2_655
C21 H16 3.0523 no . 1_665
C21 H17 3.3197 no . 1_665
C21 H18 3.3372 no . 1_665
C24 H1 3.1774 no . 2_765
C24 H10 3.5057 no . 2_665
C24 H20 3.5729 no . 2_655
C26 H3 3.3496 no . 1_445
C26 H5 3.3360 no . 1_445
C26 H11 3.3902 no . 1_445
C26 H16 3.2334 no . 2_656
C28 H1 3.1354 no . 2_765
C28 H10 3.4806 no . 2_665
C29 H10 3.5789 no . 1_545
C29 H12 3.5293 no . 1_545
C29 H13 3.5485 no . 1_545
B25 H2 3.5049 no . .
B25 H4 3.2520 no . 2_755
B25 H7 3.1534 no . 2_765
B25 H8 3.5192 no . 1_545
B25 H9 3.4843 no . 2_765
B25 H12 3.3615 no . 1_545
B25 H15 3.3254 no . 1_655
B25 H18 3.5003 no . 1_655
B25 H19 3.0551 no . 1_655
H1 F4 2.7687 no . .
H1 F31 3.5916 no . .
H1 C24 3.1774 no . 2_765
H1 C28 3.1354 no . 2_765
H1 H6 2.6926 no . 2_765
H1 H7 2.6085 no . 2_765
H2 F4 3.5101 no . .
H2 F31 2.6885 no . .
H2 O9 3.3581 no . 1_655
H2 B25 3.5049 no . .
H2 H6 3.0661 no . 2_765
H2 H7 3.2045 no . 2_765
H2 H10 3.5558 no . 1_655
H2 H14 3.1617 no . 1_655
H3 I1 3.3598 no . 2_766
H3 O3 2.9638 no . 2_766
H3 C6 3.3899 no . 2_766
H3 C16 3.5043 no . 2_766
H3 C26 3.3496 no . 1_665
H3 H3 3.0866 no . 2_766
H3 H11 3.4616 no . 2_776
H3 H13 3.2108 no . 2_776
H3 H16 3.2799 no . 1_665
H3 H17 2.7077 no . 1_665
H3 H18 3.5905 no . 1_665
H4 F4 3.3826 no . .
H4 F22 2.7991 no . 2_755
H4 F23 2.5932 no . 2_755
H4 C18 3.2568 no . 2_655
H4 C19 3.5765 no . 2_655
H4 B25 3.2520 no . 2_755
H4 H4 3.0477 no . 2_655
H4 H9 3.3938 no . 1_545
H4 H19 3.4293 no . 2_655
H4 H20 3.5170 no . 2_655
H5 I1 3.3716 no . 1_655
H5 O3 3.5823 no . 2_766
H5 O7 3.3939 no . 1_655
H5 O7 2.6949 no . 2_766
H5 O9 3.4311 no . 1_655
H5 C6 3.1982 no . 2_766
H5 C26 3.3360 no . 1_665
H5 H16 2.7318 no . 1_665
H5 H17 3.3371 no . 1_665
H5 H18 3.4378 no . 1_665
H6 F22 2.6212 no . 2_755
H6 C11 3.0848 no . 2_765
H6 C13 3.2970 no . 2_765
H6 H1 2.6926 no . 2_765
H6 H2 3.0661 no . 2_765
H6 H8 3.4438 no . 2_765
H6 H10 3.4709 no . 2_665
H6 H19 3.2455 no . 2_655
H6 H20 3.2979 no . 2_655
H7 F4 2.8064 no . 2_765
H7 F23 2.7359 no . 2_765
H7 F31 3.5864 no . 2_765
H7 C11 3.3781 no . 2_765
H7 B25 3.1534 no . 2_765
H7 H1 2.6085 no . 2_765
H7 H2 3.2045 no . 2_765
H7 H10 3.4225 no . 2_665
H8 F4 3.3162 no . 1_565
H8 F22 2.6763 no . 1_565
H8 B25 3.5192 no . 1_565
H8 H6 3.4438 no . 2_765
H8 H20 3.3172 no . 1_565
H9 F4 3.2083 no . 1_565
H9 F4 3.2585 no . 2_765
H9 F22 3.2092 no . 1_565
H9 F23 2.6559 no . 2_765
H9 B25 3.4843 no . 2_765
H9 H4 3.3938 no . 1_565
H9 H20 3.0191 no . 1_565
H10 F23 3.4954 no . 2_765
H10 C24 3.5057 no . 2_665
H10 C28 3.4806 no . 2_665
H10 C29 3.5789 no . 1_565
H10 H2 3.5558 no . 1_455
H10 H6 3.4709 no . 2_665
H10 H7 3.4225 no . 2_665
H10 H20 2.6581 no . 1_565
H11 I1 3.4712 no . 2_776
H11 O7 2.9727 no . 1_665
H11 O10 2.6048 no . 2_776
H11 C6 3.4652 no . 1_665
H11 C26 3.3902 no . 1_665
H11 H3 3.4616 no . 2_776
H11 H11 3.4878 no . 2_776
H11 H17 2.8665 no . 1_665
H11 H18 3.4224 no . 1_665
H12 F4 3.1048 no . 1_565
H12 F31 2.9097 no . 1_565
H12 C11 3.3533 no . 1_565
H12 C13 3.3420 no . 1_565
H12 C29 3.5293 no . 1_565
H12 B25 3.3615 no . 1_565
H12 H17 3.4695 no . 1_665
H12 H18 3.3066 no . 1_665
H12 H21 2.6394 no . 1_565
H13 O3 2.6658 no . 1_565
H13 C6 3.5887 no . 1_565
H13 C8 3.2949 no . 1_565
H13 C16 3.5241 no . 1_565
H13 C17 3.4012 no . 1_565
H13 C29 3.5485 no . 1_565
H13 H3 3.2108 no . 2_776
H13 H16 3.1593 no . 1_565
H13 H21 2.6943 no . 1_565
H14 F31 3.1240 no . 1_455
H14 H2 3.1617 no . 1_455
H15 F23 3.2241 no . 1_455
H15 F31 2.4330 no . 1_455
H15 B25 3.3254 no . 1_455
H16 O7 3.5111 no . 2_656
H16 O9 3.5241 no . 1_545
H16 C6 3.3518 no . 2_656
H16 C12 3.5290 no . 1_545
H16 C16 3.3579 no . 1_445
H16 C21 3.0523 no . 1_445
H16 C26 3.2334 no . 2_656
H16 H3 3.2799 no . 1_445
H16 H5 2.7318 no . 1_445
H16 H13 3.1593 no . 1_545
H16 H16 2.9178 no . 2_656
H16 H17 3.0196 no . 2_656
H17 O10 3.0491 no . 1_445
H17 O10 3.5386 no . 2_666
H17 C12 3.5454 no . 1_445
H17 C14 3.4294 no . 1_445
H17 C16 2.9603 no . 1_445
H17 C21 3.3197 no . 1_445
H17 H3 2.7077 no . 1_445
H17 H5 3.3371 no . 1_445
H17 H11 2.8665 no . 1_445
H17 H12 3.4695 no . 1_445
H17 H16 3.0196 no . 2_656
H18 F22 3.0067 no . 1_455
H18 F31 2.7968 no . 1_455
H18 C16 3.4339 no . 1_445
H18 C21 3.3372 no . 1_445
H18 B25 3.5003 no . 1_455
H18 H3 3.5905 no . 1_445
H18 H5 3.4378 no . 1_445
H18 H11 3.4224 no . 1_445
H18 H12 3.3066 no . 1_445
H19 F22 2.6938 no . 1_455
H19 F23 2.8869 no . 1_455
H19 F31 2.9141 no . 1_455
H19 O9 3.4806 no . 1_545
H19 B25 3.0551 no . 1_455
H19 H4 3.4293 no . 2_655
H19 H6 3.2455 no . 2_655
H20 F4 2.9477 no . .
H20 O9 3.0909 no . 1_545
H20 C5 3.1622 no . 1_545
H20 C24 3.5729 no . 2_655
H20 H4 3.5170 no . 2_655
H20 H6 3.2979 no . 2_655
H20 H8 3.3172 no . 1_545
H20 H9 3.0191 no . 1_545
H20 H10 2.6581 no . 1_545
H21 F4 2.8616 no . .
H21 O9 3.0271 no . 1_545
H21 C12 3.3849 no . 1_545
H21 C14 2.9926 no . 1_545
H21 H12 2.6394 no . 1_545
H21 H13 2.6943 no . 1_545

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_1390
_database_code_depnum_ccdc_archive 'CCDC 2049846'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-12-12 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2020-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 Cl O5 S'
_chemical_formula_sum            'C10 H9 Cl O5 S'
_chemical_formula_weight         276.68
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H9 Cl1 O5 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   20.5084(7)
_cell_length_b                   8.4737(2)
_cell_length_c                   6.6391(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1153.76(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2848
_cell_measurement_temperature    123
_cell_measurement_theta_max      73.2650
_cell_measurement_theta_min      4.3150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (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_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6009
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.312
_diffrn_reflns_theta_min         4.312
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     78.00 144.00   0.50    0.88    --   76.50  89.00  58.00  132
  2  ω     -1.00  33.00   0.50    0.88    --   76.50 -33.00 111.00   68
  3  ω     86.00 111.00   0.50    0.88    --   76.50 126.00 131.00   50
  4  ω   -173.00-115.00   0.50    0.88    -- -106.00 -89.00 -56.00  116
  5  ω    -82.00 -57.00   0.50    0.88    -- -106.00 145.00 -60.00   50
  6  ω   -175.00-150.00   0.50    0.88    -- -106.00-126.00  54.00   50
  7  ω    -65.00 -31.00   0.50    0.24    --  -42.93 125.00  30.00   68
  8  ω    -93.00 -68.00   0.50    0.24    --  -42.93 125.00  30.00   50
  9  ω     78.00 113.00   0.50    0.24    --   42.93 125.00 150.00   70
 10  ω     72.00 116.00   0.50    0.24    --   42.93 125.00 -30.00   88
 11  ω   -177.00-138.00   0.50    0.88    -- -106.00 -77.00-150.00   78
 12  ω   -129.00 -77.00   0.50    0.88    -- -106.00 -77.00-150.00  104
 13  ω    -78.00 -52.00   0.50    0.88    -- -106.00  96.00  88.24   52
 14  ω    -85.00 -38.00   0.50    0.88    -- -106.00  57.00 120.00   94
 15  ω   -177.00-107.00   0.50    0.88    -- -106.00 -57.00 -30.00  140
 16  ω    -72.00 -32.00   0.50    0.88    -- -106.00 125.00  90.00   80
 17  ω   -111.00 -36.00   0.50    0.88    -- -106.00 125.00 -60.00  150
 18  ω   -153.00-111.00   0.50    0.88    -- -106.00 -37.00 -30.00   84
 19  ω   -100.00 -75.00   0.50    0.88    -- -106.00 125.00   0.00   50
 20  ω    -94.00 -69.00   0.50    0.88    -- -106.00  57.00  90.00   50
 21  ω   -104.00 -79.00   0.50    0.88    -- -106.00  96.00  88.24   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0034822000
_diffrn_orient_matrix_UB_12      0.2104822000
_diffrn_orient_matrix_UB_13      -0.0761354000
_diffrn_orient_matrix_UB_21      0.0748605000
_diffrn_orient_matrix_UB_22      0.0025833000
_diffrn_orient_matrix_UB_23      -0.0154588000
_diffrn_orient_matrix_UB_31      -0.0053450000
_diffrn_orient_matrix_UB_32      -0.0977606000
_diffrn_orient_matrix_UB_33      -0.1642940000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.581
_reflns_Friedel_fraction_full    0.744
_reflns_Friedel_fraction_max     0.694
_reflns_number_gt                1849
_reflns_number_total             2022
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (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         0.996
_refine_diff_density_min         -1.055
_refine_diff_density_rms         0.154
_refine_ls_abs_structure_details 
;
 Flack x determined using 580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.50(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2022
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.1023
_refine_ls_restrained_S_all      1.071
_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)+(0.0724P)²+12.1897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2539
_refine_ls_wR_factor_ref         0.2606
_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:
 C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00F,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00D(H00D)
2.d Idealised Me refined as rotating group:
 C00F(H00A,H00C,H00E)
;
_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 0.74100(11) 0.4371(2) 0.6689(5) 0.0285(6) Uani 1 1 d . . . . .
Cl02 Cl 0.35549(15) 0.0605(4) 0.1832(14) 0.092(2) Uani 1 1 d . . . . .
O003 O 0.4968(4) 0.6408(9) 0.175(2) 0.048(2) Uani 1 1 d . . . . .
O004 O 0.6996(6) 0.4381(14) 0.4785(19) 0.051(3) Uani 1 1 d . . . . .
O005 O 0.7866(4) 0.5630(9) 0.7017(13) 0.037(2) Uani 1 1 d . . . . .
O6 O 0.5926(4) 0.5170(9) 0.161(4) 0.086(5) Uani 1 1 d . . . . .
C007 C 0.5039(5) 0.3538(11) 0.163(2) 0.030(2) Uani 1 1 d . . . . .
C008 C 0.5577(5) 0.2566(11) 0.153(3) 0.042(3) Uani 1 1 d . . . . .
C009 C 0.4402(5) 0.3014(12) 0.161(3) 0.041(3) Uani 1 1 d . . . . .
H009 H 0.403928 0.371137 0.164195 0.049 Uiso 1 1 calc R . . . .
C00A C 0.5272(5) 0.5197(12) 0.163(3) 0.044(3) Uani 1 1 d . . . . .
C00B C 0.5492(5) 0.0927(12) 0.148(3) 0.037(3) Uani 1 1 d . . . . .
H00B H 0.585431 0.022815 0.146424 0.044 Uiso 1 1 calc R . . . .
O00C O 0.6980(6) 0.4351(15) 0.847(3) 0.073(5) Uani 1 1 d . . . . .
C00D C 0.4868(5) 0.0378(11) 0.147(2) 0.031(2) Uani 1 1 d . . . . .
H00D H 0.479490 -0.072781 0.141203 0.037 Uiso 1 1 calc R . . . .
C00E C 0.4335(5) 0.1385(12) 0.155(3) 0.037(3) Uani 1 1 d . . . . .
C00F C 0.7833(6) 0.2582(13) 0.680(3) 0.045(3) Uani 1 1 d . . . . .
H00A H 0.754260 0.175208 0.729636 0.068 Uiso 1 1 calc GR . . . .
H00C H 0.820721 0.268839 0.770547 0.068 Uiso 1 1 calc GR . . . .
H00E H 0.798796 0.230149 0.544543 0.068 Uiso 1 1 calc GR . . . .
C00G C 0.6171(6) 0.3578(13) 0.227(2) 0.037(3) Uani 1 1 d . . . . .
H00G H 0.653444 0.332038 0.131563 0.045 Uiso 1 1 calc R . . . .
C00H C 0.6450(6) 0.3294(15) 0.435(2) 0.036(3) Uani 1 1 d . . . . .
H00F H 0.610270 0.344540 0.537188 0.043 Uiso 1 1 calc R . . . .
H00H H 0.660544 0.219024 0.445349 0.043 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O004 1.523(12) . ?
S1 O005 1.435(8) . ?
S1 O00C 1.475(14) . ?
S1 C00F 1.749(10) . ?
Cl02 C00E 1.740(11) . ?
O003 C00A 1.203(13) . ?
O004 C00H 1.478(16) . ?
O6 C00A 1.341(14) . ?
O6 C00G 1.505(16) . ?
C007 C008 1.378(14) . ?
C007 C009 1.380(14) . ?
C007 C00A 1.485(14) . ?
C008 C00B 1.399(14) . ?
C008 C00G 1.569(15) . ?
C009 C00E 1.388(15) . ?
C00B C00D 1.363(15) . ?
C00D C00E 1.387(15) . ?
C00G C00H 1.519(19) . ?

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
O004 S1 C00F 108.4(9) . . ?
O005 S1 O004 119.0(6) . . ?
O005 S1 O00C 106.1(7) . . ?
O005 S1 C00F 108.3(6) . . ?
O00C S1 O004 109.4(6) . . ?
O00C S1 C00F 104.7(8) . . ?
C00H O004 S1 125.4(9) . . ?
C00A O6 C00G 110.2(10) . . ?
C008 C007 C009 124.4(9) . . ?
C008 C007 C00A 108.0(9) . . ?
C009 C007 C00A 127.5(9) . . ?
C007 C008 C00B 119.6(10) . . ?
C007 C008 C00G 106.3(9) . . ?
C00B C008 C00G 130.2(10) . . ?
C007 C009 C00E 114.5(9) . . ?
O003 C00A O6 122.2(10) . . ?
O003 C00A C007 129.9(10) . . ?
O6 C00A C007 107.8(9) . . ?
C00D C00B C008 117.1(9) . . ?
C00B C00D C00E 122.0(9) . . ?
C009 C00E Cl02 117.8(9) . . ?
C00D C00E Cl02 119.6(8) . . ?
C00D C00E C009 122.3(10) . . ?
O6 C00G C008 98.0(9) . . ?
O6 C00G C00H 122.2(13) . . ?
C00H C00G C008 119.4(11) . . ?
O004 C00H C00G 111.3(10) . . ?

_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 3.060
_oxdiff_exptl_absorpt_empirical_full_min 0.449
####################################################################### 
# 
# 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_520
_database_code_depnum_ccdc_archive 'CCDC 2049847'
loop_
_audit_author_name
_audit_author_address
'Yoshihiro Nishimoto'
;Osaka University
Japan
;
_audit_update_record             
;
2020-12-12 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2020-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H9 Cl O5 S'
_chemical_formula_sum            'C10 H9 Cl O5 S'
_chemical_formula_weight         276.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H9 Cl1 O5 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'
Cl Cl 0.1484 0.1585 '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                   6.9697(3)
_cell_length_b                   13.7195(5)
_cell_length_c                   11.4237(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.265(3)
_cell_angle_gamma                90
_cell_volume                     1090.57(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5634
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.5510
_cell_measurement_theta_min      2.3240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9586
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.745
_diffrn_reflns_theta_min         2.322
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.797
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  64.00   0.50    1.20    --   -5.03  48.00 114.00  158
  2  ω    -26.00  28.00   0.50    1.20    --   -5.03 -99.00 150.00  108
  3  ω    -13.00  13.00   0.50    1.20    --   -5.03 -99.00   0.00   52
  4  ω    -26.00   1.00   0.50    1.20    --   -5.03 -99.00 -90.00   54
  5  ω    -75.00 -12.00   0.50    1.20    --   -5.03 -48.00 -33.00  126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0879226000
_diffrn_orient_matrix_UB_12      0.0235056000
_diffrn_orient_matrix_UB_13      -0.0106946000
_diffrn_orient_matrix_UB_21      0.0035790000
_diffrn_orient_matrix_UB_22      0.0197443000
_diffrn_orient_matrix_UB_23      0.0574824000
_diffrn_orient_matrix_UB_31      0.0514481000
_diffrn_orient_matrix_UB_32      -0.0415718000
_diffrn_orient_matrix_UB_33      0.0212769000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2411
_reflns_number_total             2708
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.409
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.068
_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)+(0.0370P)²+0.6024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0833
_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:
 C00D(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00E(H00E), C00G(H00G)
2.d Idealised Me refined as rotating group:
 C00H(H00C,H00F,H00H)
;
_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
S001 S 0.23753(5) 0.53614(3) 0.11641(3) 0.01592(11) Uani 1 1 d . . . . .
Cl02 Cl 0.90281(6) 0.28773(3) 0.58515(3) 0.02109(11) Uani 1 1 d . . . . .
O003 O 0.61325(16) 0.69257(8) 0.36943(10) 0.0194(2) Uani 1 1 d . . . . .
O004 O 0.37286(16) 0.56307(8) 0.22667(10) 0.0181(2) Uani 1 1 d . . . . .
O005 O 0.66703(17) 0.65717(8) 0.55652(10) 0.0235(3) Uani 1 1 d . . . . .
O006 O 0.05252(17) 0.57054(9) 0.14422(11) 0.0258(3) Uani 1 1 d . . . . .
O007 O 0.32035(18) 0.57160(9) 0.01323(10) 0.0232(3) Uani 1 1 d . . . . .
C008 C 0.7801(2) 0.46363(10) 0.50899(13) 0.0148(3) Uani 1 1 d . . . . .
H008 H 0.802711 0.484960 0.587686 0.018 Uiso 1 1 calc R . . . .
C009 C 0.7072(2) 0.52751(10) 0.42211(13) 0.0144(3) Uani 1 1 d . . . . .
C00A C 0.6715(2) 0.49498(11) 0.30724(13) 0.0158(3) Uani 1 1 d . . . . .
C00B C 0.6638(2) 0.62962(11) 0.45668(14) 0.0160(3) Uani 1 1 d . . . . .
C00C C 0.8185(2) 0.36881(11) 0.47754(13) 0.0153(3) Uani 1 1 d . . . . .
C00D C 0.5847(2) 0.56583(11) 0.21906(14) 0.0169(3) Uani 1 1 d . . . . .
H00D H 0.620923 0.548437 0.138214 0.020 Uiso 1 1 calc R . . . .
C00E C 0.7162(2) 0.39931(11) 0.27769(14) 0.0192(3) Uani 1 1 d . . . . .
H00E H 0.695204 0.377540 0.199063 0.023 Uiso 1 1 calc R . . . .
C00F C 0.6480(2) 0.66756(11) 0.24975(14) 0.0203(3) Uani 1 1 d . . . . .
H00A H 0.787008 0.674001 0.237799 0.024 Uiso 1 1 calc R . . . .
H00B H 0.578380 0.714017 0.196352 0.024 Uiso 1 1 calc R . . . .
C00G C 0.7913(2) 0.33611(11) 0.36293(14) 0.0189(3) Uani 1 1 d . . . . .
H00G H 0.823728 0.271132 0.343168 0.023 Uiso 1 1 calc R . . . .
C00H C 0.2388(3) 0.40884(12) 0.11577(17) 0.0279(4) Uani 1 1 d . . . . .
H00C H 0.366921 0.385448 0.098218 0.042 Uiso 1 1 calc GR . . . .
H00F H 0.144072 0.384986 0.055852 0.042 Uiso 1 1 calc GR . . . .
H00H H 0.206276 0.384645 0.192880 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
S001 O004 1.5739(11) . ?
S001 O006 1.4259(12) . ?
S001 O007 1.4272(12) . ?
S001 C00H 1.7466(17) . ?
Cl02 C00C 1.7353(15) . ?
O003 C00B 1.3503(19) . ?
O003 C00F 1.443(2) . ?
O004 C00D 1.4847(19) . ?
O005 C00B 1.2005(19) . ?
C008 C009 1.398(2) . ?
C008 C00C 1.380(2) . ?
C009 C00A 1.395(2) . ?
C009 C00B 1.491(2) . ?
C00A C00D 1.502(2) . ?
C00A C00E 1.395(2) . ?
C00C C00G 1.387(2) . ?
C00D C00F 1.499(2) . ?
C00E C00G 1.384(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O004 S001 C00H 103.59(7) . . ?
O006 S001 O004 104.62(7) . . ?
O006 S001 O007 118.99(7) . . ?
O006 S001 C00H 109.69(9) . . ?
O007 S001 O004 109.20(7) . . ?
O007 S001 C00H 109.57(8) . . ?
C00B O003 C00F 119.76(12) . . ?
C00D O004 S001 120.79(10) . . ?
C00C C008 C009 118.32(14) . . ?
C008 C009 C00B 118.17(13) . . ?
C00A C009 C008 120.36(13) . . ?
C00A C009 C00B 121.45(13) . . ?
C009 C00A C00D 117.86(13) . . ?
C00E C00A C009 119.89(14) . . ?
C00E C00A C00D 122.25(14) . . ?
O003 C00B C009 116.98(13) . . ?
O005 C00B O003 119.34(14) . . ?
O005 C00B C009 123.66(14) . . ?
C008 C00C Cl02 118.87(12) . . ?
C008 C00C C00G 122.18(14) . . ?
C00G C00C Cl02 118.95(12) . . ?
O004 C00D C00A 107.93(12) . . ?
O004 C00D C00F 106.88(12) . . ?
C00F C00D C00A 110.11(13) . . ?
C00G C00E C00A 120.00(15) . . ?
O003 C00F C00D 112.32(12) . . ?
C00E C00G C00C 119.17(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 1.208
_oxdiff_exptl_absorpt_empirical_full_min 0.874
