# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

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

data_7a
_database_code_depnum_ccdc_archive 'CCDC 2088342'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-09 downloaded from the CCDC.
;
_audit_creation_date             2019-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H23 F3 N2 O3 S'
_chemical_formula_sum            'C33 H23 F3 N2 O3 S'
_chemical_formula_weight         584.59
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   14.8873(3)
_cell_length_b                   14.8873(3)
_cell_length_c                   13.6624(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3028.01(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5935
_cell_measurement_temperature    223(100)
_cell_measurement_theta_max      72.5660
_cell_measurement_theta_min      4.2250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10549
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.498
_diffrn_reflns_theta_min         4.392
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      223(100)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000 -180.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   92.0000   14.1736 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -33.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421    0.0000  -60.0000 138

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   91.00   1.0000    2.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega  100.00  178.00   1.0000    2.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 78

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000    2.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   90.00  175.00   1.0000    2.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   90.0000 85

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000    2.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   81.00  135.00   1.0000    2.1500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1023653000
_diffrn_orient_matrix_UB_12      -0.0045943000
_diffrn_orient_matrix_UB_13      0.0161178000
_diffrn_orient_matrix_UB_21      0.0070562000
_diffrn_orient_matrix_UB_22      -0.0737107000
_diffrn_orient_matrix_UB_23      -0.0787584000
_diffrn_orient_matrix_UB_31      0.0138876000
_diffrn_orient_matrix_UB_32      0.0724430000
_diffrn_orient_matrix_UB_33      -0.0790055000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                5469
_reflns_number_total             5627
_reflns_odcompleteness_completeness 98.55
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.506
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.155
_refine_ls_abs_structure_details 
;
 Flack x determined using 2343 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5627
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0789
_refine_ls_restrained_S_all      1.055
_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)+(0.1714P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1983
_refine_ls_wR_factor_ref         0.2009
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00F(H00F), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C015(H015)
2.c Idealised Me refined as rotating group:
 C016(H01A,H01B,H01C)
;
_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
S001 S 0.23484(7) 0.33525(6) 0.35749(7) 0.0238(3) Uani 1 1 d . . . . .
F002 F 0.0267(2) 0.7505(2) 0.5759(2) 0.0375(7) Uani 1 1 d . . . . .
F003 F 0.0968(2) 0.78318(19) 0.4436(3) 0.0388(7) Uani 1 1 d . . . . .
F004 F -0.0476(2) 0.7701(2) 0.4429(3) 0.0392(7) Uani 1 1 d . . . . .
O005 O 0.2600(2) 0.6661(2) 0.3908(3) 0.0290(7) Uani 1 1 d . . . . .
O006 O 0.3017(2) 0.3125(2) 0.4287(3) 0.0347(8) Uani 1 1 d . . . . .
O007 O 0.2579(2) 0.3228(2) 0.2572(3) 0.0330(8) Uani 1 1 d . . . . .
N008 N 0.1949(3) 0.4375(3) 0.3733(3) 0.0279(8) Uani 1 1 d . . . . .
C009 C 0.1260(3) 0.6134(3) 0.3089(3) 0.0281(9) Uani 1 1 d . . . . .
H009 H 0.1410 0.6113 0.2429 0.034 Uiso 1 1 calc R . . . .
C00A C 0.1320(3) 0.5953(3) 0.4834(3) 0.0210(8) Uani 1 1 d . . . . .
H00A H 0.1193 0.5313 0.4929 0.025 Uiso 1 1 calc R . . . .
C00B C 0.1728(3) 0.6241(3) 0.5808(3) 0.0255(9) Uani 1 1 d . . . . .
C00C C -0.0390(3) 0.5769(3) 0.4926(3) 0.0240(8) Uani 1 1 d . . . . .
C00D C 0.3410(3) 0.6248(3) 0.3814(3) 0.0275(9) Uani 1 1 d . . . . .
N00E N -0.0960(4) 0.6536(4) 0.2342(4) 0.0535(14) Uani 1 1 d . . . . .
C00F C -0.1055(3) 0.6057(3) 0.5560(3) 0.0288(9) Uani 1 1 d . . . . .
H00F H -0.1050 0.6646 0.5787 0.035 Uiso 1 1 calc R . . . .
C00G C 0.3365(3) 0.5315(3) 0.3707(3) 0.0259(9) Uani 1 1 d . . . . .
C00H C 0.0380(3) 0.6360(3) 0.4539(3) 0.0232(8) Uani 1 1 d . . . . .
C00I C 0.2429(3) 0.5085(3) 0.3764(3) 0.0243(8) Uani 1 1 d . . . . .
C00J C -0.0333(4) 0.6439(4) 0.2809(4) 0.0357(11) Uani 1 1 d . . . . .
C00K C 0.0275(3) 0.7350(3) 0.4823(4) 0.0320(10) Uani 1 1 d . . . . .
C00L C 0.0439(3) 0.6312(3) 0.3420(3) 0.0274(9) Uani 1 1 d . . . . .
C00M C 0.1357(3) 0.2750(3) 0.3836(4) 0.0297(9) Uani 1 1 d . . . . .
C00N C 0.2252(3) 0.7008(3) 0.5945(4) 0.0306(9) Uani 1 1 d . . . . .
H00N H 0.2361 0.7390 0.5419 0.037 Uiso 1 1 calc R . . . .
C00O C 0.0630(3) 0.2856(3) 0.3214(4) 0.0344(10) Uani 1 1 d . . . . .
H00O H 0.0659 0.3244 0.2681 0.041 Uiso 1 1 calc R . . . .
C00P C 0.4982(3) 0.6209(4) 0.3720(4) 0.0368(11) Uani 1 1 d . . . . .
H00P H 0.5535 0.6498 0.3729 0.044 Uiso 1 1 calc R . . . .
C00Q C 0.1923(3) 0.5970(3) 0.3906(3) 0.0236(8) Uani 1 1 d . . . . .
C00R C 0.2611(4) 0.7209(4) 0.6852(5) 0.0428(13) Uani 1 1 d . . . . .
H00R H 0.2968 0.7717 0.6932 0.051 Uiso 1 1 calc R . . . .
C00S C 0.1550(3) 0.5697(3) 0.6608(4) 0.0314(10) Uani 1 1 d . . . . .
H00S H 0.1188 0.5193 0.6533 0.038 Uiso 1 1 calc R . . . .
C00T C -0.0410(3) 0.4877(3) 0.4606(4) 0.0290(9) Uani 1 1 d . . . . .
H00T H 0.0027 0.4675 0.4173 0.035 Uiso 1 1 calc R . . . .
C00U C 0.4956(3) 0.5274(4) 0.3594(4) 0.0358(10) Uani 1 1 d . . . . .
H00U H 0.5490 0.4958 0.3516 0.043 Uiso 1 1 calc R . . . .
C00V C -0.1728(4) 0.5477(4) 0.5859(4) 0.0373(11) Uani 1 1 d . . . . .
H00V H -0.2176 0.5683 0.6277 0.045 Uiso 1 1 calc R . . . .
C00W C -0.1071(4) 0.4292(4) 0.4922(4) 0.0348(10) Uani 1 1 d . . . . .
H00W H -0.1065 0.3695 0.4720 0.042 Uiso 1 1 calc R . . . .
C00X C 0.1906(4) 0.5897(4) 0.7513(4) 0.0418(12) Uani 1 1 d . . . . .
H00X H 0.1789 0.5522 0.8042 0.050 Uiso 1 1 calc R . . . .
C00Y C 0.4157(3) 0.4820(3) 0.3582(4) 0.0300(9) Uani 1 1 d . . . . .
H00Y H 0.4140 0.4200 0.3495 0.036 Uiso 1 1 calc R . . . .
C00Z C 0.4216(4) 0.6707(4) 0.3832(4) 0.0350(11) Uani 1 1 d . . . . .
H00Z H 0.4238 0.7327 0.3916 0.042 Uiso 1 1 calc R . . . .
C010 C -0.1743(3) 0.4599(4) 0.5544(4) 0.0340(10) Uani 1 1 d . . . . .
H010 H -0.2199 0.4215 0.5745 0.041 Uiso 1 1 calc R . . . .
C011 C 0.1323(5) 0.2203(5) 0.4625(5) 0.0519(15) Uani 1 1 d . . . . .
H011 H 0.1818 0.2142 0.5035 0.062 Uiso 1 1 calc R . . . .
C012 C 0.2439(4) 0.6652(5) 0.7642(4) 0.0457(14) Uani 1 1 d . . . . .
H012 H 0.2678 0.6783 0.8254 0.055 Uiso 1 1 calc R . . . .
C013 C -0.0137(4) 0.2370(4) 0.3407(5) 0.0449(14) Uani 1 1 d . . . . .
H013 H -0.0628 0.2426 0.2989 0.054 Uiso 1 1 calc R . . . .
C014 C -0.0197(5) 0.1810(5) 0.4191(7) 0.0621(19) Uani 1 1 d . . . . .
C015 C 0.0536(7) 0.1733(7) 0.4812(7) 0.079(3) Uani 1 1 d . . . . .
H015 H 0.0500 0.1363 0.5359 0.095 Uiso 1 1 calc R . . . .
C016 C -0.1066(8) 0.1306(9) 0.4360(12) 0.108(5) Uani 1 1 d . . . . .
H01A H -0.1083 0.1088 0.5022 0.162 Uiso 1 1 calc GR . . . .
H01B H -0.1102 0.0807 0.3916 0.162 Uiso 1 1 calc GR . . . .
H01C H -0.1566 0.1701 0.4251 0.162 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 O006 1.432(4) . ?
S001 O007 1.424(4) . ?
S001 N008 1.649(4) . ?
S001 C00M 1.764(5) . ?
F002 C00K 1.300(6) . ?
F003 C00K 1.363(6) . ?
F004 C00K 1.347(6) . ?
O005 C00D 1.360(6) . ?
O005 C00Q 1.440(5) . ?
N008 C00I 1.276(6) . ?
C009 H009 0.9300 . ?
C009 C00L 1.330(7) . ?
C009 C00Q 1.509(6) . ?
C00A H00A 0.9800 . ?
C00A C00B 1.525(6) . ?
C00A C00H 1.578(6) . ?
C00A C00Q 1.553(6) . ?
C00B C00N 1.396(6) . ?
C00B C00S 1.385(7) . ?
C00C C00F 1.383(6) . ?
C00C C00H 1.539(6) . ?
C00C C00T 1.398(6) . ?
C00D C00G 1.397(6) . ?
C00D C00Z 1.382(7) . ?
N00E C00J 1.140(8) . ?
C00F H00F 0.9300 . ?
C00F C00V 1.385(8) . ?
C00G C00I 1.437(6) . ?
C00G C00Y 1.401(6) . ?
C00H C00K 1.532(6) . ?
C00H C00L 1.533(6) . ?
C00I C00Q 1.530(6) . ?
C00J C00L 1.433(7) . ?
C00M C00O 1.385(7) . ?
C00M C011 1.352(8) . ?
C00N H00N 0.9300 . ?
C00N C00R 1.382(7) . ?
C00O H00O 0.9300 . ?
C00O C013 1.377(8) . ?
C00P H00P 0.9300 . ?
C00P C00U 1.404(8) . ?
C00P C00Z 1.368(8) . ?
C00R H00R 0.9300 . ?
C00R C012 1.385(10) . ?
C00S H00S 0.9300 . ?
C00S C00X 1.378(8) . ?
C00T H00T 0.9300 . ?
C00T C00W 1.383(7) . ?
C00U H00U 0.9300 . ?
C00U C00Y 1.368(7) . ?
C00V H00V 0.9300 . ?
C00V C010 1.376(8) . ?
C00W H00W 0.9300 . ?
C00W C010 1.390(7) . ?
C00X H00X 0.9300 . ?
C00X C012 1.386(10) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C010 H010 0.9300 . ?
C011 H011 0.9300 . ?
C011 C015 1.389(10) . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C013 C014 1.361(12) . ?
C014 C015 1.388(14) . ?
C014 C016 1.513(9) . ?
C015 H015 0.9300 . ?
C016 H01A 0.9600 . ?
C016 H01B 0.9600 . ?
C016 H01C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O006 S001 N008 112.3(2) . . ?
O006 S001 C00M 108.9(2) . . ?
O007 S001 O006 117.1(2) . . ?
O007 S001 N008 109.4(2) . . ?
O007 S001 C00M 109.3(2) . . ?
N008 S001 C00M 98.1(2) . . ?
C00D O005 C00Q 107.3(3) . . ?
C00I N008 S001 124.5(3) . . ?
C00L C009 H009 123.8 . . ?
C00L C009 C00Q 112.4(4) . . ?
C00Q C009 H009 123.8 . . ?
C00B C00A H00A 103.6 . . ?
C00B C00A C00H 117.9(3) . . ?
C00B C00A C00Q 118.5(4) . . ?
C00H C00A H00A 103.6 . . ?
C00Q C00A H00A 103.6 . . ?
C00Q C00A C00H 107.3(3) . . ?
C00N C00B C00A 124.8(4) . . ?
C00S C00B C00A 116.6(4) . . ?
C00S C00B C00N 118.6(4) . . ?
C00F C00C C00H 124.8(4) . . ?
C00F C00C C00T 118.4(4) . . ?
C00T C00C C00H 116.8(4) . . ?
O005 C00D C00G 114.6(4) . . ?
O005 C00D C00Z 123.0(5) . . ?
C00Z C00D C00G 122.4(5) . . ?
C00C C00F H00F 119.7 . . ?
C00C C00F C00V 120.6(4) . . ?
C00V C00F H00F 119.7 . . ?
C00D C00G C00I 106.2(4) . . ?
C00D C00G C00Y 119.7(4) . . ?
C00Y C00G C00I 134.2(4) . . ?
C00C C00H C00A 110.7(3) . . ?
C00K C00H C00A 113.3(4) . . ?
C00K C00H C00C 112.8(4) . . ?
C00K C00H C00L 107.6(4) . . ?
C00L C00H C00A 100.7(3) . . ?
C00L C00H C00C 111.0(4) . . ?
N008 C00I C00G 137.6(4) . . ?
N008 C00I C00Q 116.2(4) . . ?
C00G C00I C00Q 106.2(4) . . ?
N00E C00J C00L 178.4(7) . . ?
F002 C00K F003 107.1(4) . . ?
F002 C00K F004 108.5(4) . . ?
F002 C00K C00H 114.9(4) . . ?
F003 C00K C00H 109.3(4) . . ?
F004 C00K F003 105.7(4) . . ?
F004 C00K C00H 110.9(4) . . ?
C009 C00L C00H 113.6(4) . . ?
C009 C00L C00J 124.4(5) . . ?
C00J C00L C00H 121.9(4) . . ?
C00O C00M S001 118.2(4) . . ?
C011 C00M S001 119.9(4) . . ?
C011 C00M C00O 121.9(5) . . ?
C00B C00N H00N 119.5 . . ?
C00R C00N C00B 120.9(5) . . ?
C00R C00N H00N 119.5 . . ?
C00M C00O H00O 121.0 . . ?
C013 C00O C00M 118.1(5) . . ?
C013 C00O H00O 121.0 . . ?
C00U C00P H00P 119.0 . . ?
C00Z C00P H00P 119.0 . . ?
C00Z C00P C00U 121.9(5) . . ?
O005 C00Q C009 110.1(3) . . ?
O005 C00Q C00A 114.5(3) . . ?
O005 C00Q C00I 105.7(3) . . ?
C009 C00Q C00A 103.2(3) . . ?
C009 C00Q C00I 111.6(4) . . ?
C00I C00Q C00A 111.9(3) . . ?
C00N C00R H00R 120.1 . . ?
C00N C00R C012 119.8(5) . . ?
C012 C00R H00R 120.1 . . ?
C00B C00S H00S 119.7 . . ?
C00X C00S C00B 120.5(5) . . ?
C00X C00S H00S 119.7 . . ?
C00C C00T H00T 119.5 . . ?
C00W C00T C00C 121.0(4) . . ?
C00W C00T H00T 119.5 . . ?
C00P C00U H00U 119.5 . . ?
C00Y C00U C00P 121.0(5) . . ?
C00Y C00U H00U 119.5 . . ?
C00F C00V H00V 119.6 . . ?
C010 C00V C00F 120.7(5) . . ?
C010 C00V H00V 119.6 . . ?
C00T C00W H00W 120.2 . . ?
C00T C00W C010 119.7(5) . . ?
C010 C00W H00W 120.2 . . ?
C00S C00X H00X 119.7 . . ?
C00S C00X C012 120.6(5) . . ?
C012 C00X H00X 119.7 . . ?
C00G C00Y H00Y 121.0 . . ?
C00U C00Y C00G 118.1(4) . . ?
C00U C00Y H00Y 121.0 . . ?
C00D C00Z H00Z 121.5 . . ?
C00P C00Z C00D 116.9(5) . . ?
C00P C00Z H00Z 121.5 . . ?
C00V C010 C00W 119.5(5) . . ?
C00V C010 H010 120.2 . . ?
C00W C010 H010 120.2 . . ?
C00M C011 H011 120.6 . . ?
C00M C011 C015 118.8(7) . . ?
C015 C011 H011 120.6 . . ?
C00R C012 C00X 119.5(5) . . ?
C00R C012 H012 120.2 . . ?
C00X C012 H012 120.2 . . ?
C00O C013 H013 119.1 . . ?
C014 C013 C00O 121.8(6) . . ?
C014 C013 H013 119.1 . . ?
C013 C014 C015 118.7(6) . . ?
C013 C014 C016 118.7(9) . . ?
C015 C014 C016 122.6(9) . . ?
C011 C015 H015 119.7 . . ?
C014 C015 C011 120.7(7) . . ?
C014 C015 H015 119.7 . . ?
C014 C016 H01A 109.5 . . ?
C014 C016 H01B 109.5 . . ?
C014 C016 H01C 109.5 . . ?
H01A C016 H01B 109.5 . . ?
H01A C016 H01C 109.5 . . ?
H01B C016 H01C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-04-24
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ent-5a
_database_code_depnum_ccdc_archive 'CCDC 2088343'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-09 downloaded from the CCDC.
;
_audit_creation_date             2018-12-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H23 F3 N2 O2 S2'
_chemical_formula_sum            'C33 H23 F3 N2 O2 S2'
_chemical_formula_weight         600.65
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.71838(15)
_cell_length_b                   13.40753(16)
_cell_length_c                   18.3196(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2878.27(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8764
_cell_measurement_temperature    204(6)
_cell_measurement_theta_max      72.7740
_cell_measurement_theta_min      3.7460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16816
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.726
_diffrn_reflns_theta_min         4.086
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      204(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00    1.00    --  -36.29  57.00-120.00   84
  2  ω     23.00  90.00   1.00    1.00    --   36.29-125.00 -30.00   67
  3  ω    -31.00  53.00   1.00    1.00    --   36.29 -57.00 -60.00   84
  4  ω     23.00  90.00   1.00    1.00    --   36.29-125.00 120.00   67
  5  ω    -31.00  63.00   1.00    1.00    --   36.29 -77.00 150.00   94
  6  ω     91.00 176.00   1.00    2.59    --  108.71  61.00 150.00   85
  7  ω     37.00 147.00   1.00    2.59    --  108.71 -15.00  90.00  110
  8  ω     39.00 109.00   1.00    2.59    --  108.71 -94.00 -60.00   70
  9  ω     42.00 127.00   1.00    2.59    --  108.71 -61.00  90.00   85
 10  ω    100.00 178.00   1.00    2.59    --  108.71 111.00-153.00   78
 11  ω     39.00 109.00   1.00    2.59    --  108.71 -94.00-120.00   70
 12  ω     39.00 130.00   1.00    2.59    --  108.71 -30.00   0.00   91
 13  ω   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00  90.00   84
 14  ω   -103.00 -15.00   1.00    1.00    --  -36.29 -68.00  -6.00   88
 15  ω   -104.00 -61.00   1.00    1.00    --  -36.29 -57.00-180.00   43
 16  ω   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00-120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1211700000
_diffrn_orient_matrix_UB_12      0.0435658000
_diffrn_orient_matrix_UB_13      0.0071351000
_diffrn_orient_matrix_UB_21      -0.0446156000
_diffrn_orient_matrix_UB_22      0.0779072000
_diffrn_orient_matrix_UB_23      0.0548561000
_diffrn_orient_matrix_UB_31      0.0250367000
_diffrn_orient_matrix_UB_32      -0.0723460000
_diffrn_orient_matrix_UB_33      0.0632902000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                5432
_reflns_number_total             5640
_reflns_odcompleteness_completeness 99.93
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.318
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.145
_refine_ls_abs_structure_details 
;
 Flack x determined using 2276 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.009(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.057
_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)+(0.0978P)²+0.2374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1289
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y), C00Z(H00Z),
 C010(H010), C011(H011), C012(H012), C014(H014), C015(H015), C016(H016)
2.c Idealised Me refined as rotating group:
 C013(H01A,H01B,H01C)
;
_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
S001 S 0.34105(6) 0.55138(5) 0.74600(4) 0.02820(19) Uani 1 1 d . . . . .
S002 S 0.23826(8) 0.18400(6) 0.69849(5) 0.0383(2) Uani 1 1 d . . . . .
O003 O 0.4429(2) 0.60909(17) 0.73954(13) 0.0378(5) Uani 1 1 d . . . . .
O004 O 0.2666(2) 0.56752(19) 0.80632(12) 0.0402(6) Uani 1 1 d . . . . .
F005 F 0.8054(2) 0.4304(3) 0.80489(16) 0.0734(9) Uani 1 1 d . . . . .
N006 N 0.3858(2) 0.43274(19) 0.75073(14) 0.0261(5) Uani 1 1 d . . . . .
F007 F 0.8210(3) 0.3099(3) 0.7318(2) 0.0955(13) Uani 1 1 d . . . . .
N008 N 0.5819(3) 0.3150(2) 0.85708(17) 0.0451(8) Uani 1 1 d . . . . .
C009 C 0.2032(3) 0.3310(3) 0.79220(17) 0.0315(7) Uani 1 1 d . . . . .
C00A C 0.5898(3) 0.3532(2) 0.80156(17) 0.0301(6) Uani 1 1 d . . . . .
C00B C 0.5915(3) 0.4021(2) 0.73129(16) 0.0270(6) Uani 1 1 d . . . . .
C00C C 0.4752(2) 0.4065(2) 0.69557(16) 0.0250(5) Uani 1 1 d . . . . .
H00C H 0.4758 0.4565 0.6566 0.030 Uiso 1 1 calc R . . . .
C00D C 0.4425(3) 0.2992(2) 0.58025(17) 0.0301(6) Uani 1 1 d . . . . .
C00E C 0.4429(3) 0.3012(2) 0.66284(17) 0.0271(6) Uani 1 1 d . . . . .
H00E H 0.4982 0.2519 0.6804 0.033 Uiso 1 1 calc R . . . .
C00F C 0.6888(3) 0.4312(3) 0.69942(19) 0.0343(7) Uani 1 1 d . . . . .
C00G C 0.3099(3) 0.6014(2) 0.60321(18) 0.0333(7) Uani 1 1 d . . . . .
H00G H 0.3818 0.6307 0.6054 0.040 Uiso 1 1 calc R . . . .
C00H C 0.3033(3) 0.3538(2) 0.74986(17) 0.0275(6) Uani 1 1 d . . . . .
C00I C 0.6958(3) 0.4845(3) 0.62802(19) 0.0369(7) Uani 1 1 d . . . . .
C00J C 0.3313(3) 0.2834(2) 0.70036(17) 0.0287(6) Uani 1 1 d . . . . .
F00K F 0.8869(2) 0.4521(5) 0.7062(2) 0.1213(19) Uani 1 1 d . . . . .
C00L C 0.2492(3) 0.6007(3) 0.53833(18) 0.0377(7) Uani 1 1 d . . . . .
H00L H 0.2798 0.6318 0.4973 0.045 Uiso 1 1 calc R . . . .
C00M C 0.3562(3) 0.3459(3) 0.54103(18) 0.0355(7) Uani 1 1 d . . . . .
H00M H 0.2960 0.3761 0.5656 0.043 Uiso 1 1 calc R . . . .
C00N C 0.1552(3) 0.5133(2) 0.66157(18) 0.0324(6) Uani 1 1 d . . . . .
H00N H 0.1233 0.4851 0.7032 0.039 Uiso 1 1 calc R . . . .
C00O C 0.2628(3) 0.5583(2) 0.66443(16) 0.0291(6) Uani 1 1 d . . . . .
C00P C 0.0970(3) 0.5113(3) 0.5962(2) 0.0384(8) Uani 1 1 d . . . . .
H00P H 0.0258 0.4808 0.5938 0.046 Uiso 1 1 calc R . . . .
C00Q C 0.6560(3) 0.5819(3) 0.6228(2) 0.0431(8) Uani 1 1 d . . . . .
H00Q H 0.6225 0.6126 0.6630 0.052 Uiso 1 1 calc R . . . .
C00R C 0.1470(3) 0.3807(3) 0.84893(19) 0.0400(8) Uani 1 1 d . . . . .
H00R H 0.1751 0.4409 0.8666 0.048 Uiso 1 1 calc R . . . .
C00S C 0.1433(3) 0.5543(3) 0.53353(19) 0.0382(7) Uani 1 1 d . . . . .
C00T C 0.1578(3) 0.2395(3) 0.7674(2) 0.0385(8) Uani 1 1 d . . . . .
C00U C 0.0060(3) 0.2503(4) 0.8533(3) 0.0550(11) Uani 1 1 d . . . . .
H00U H -0.0598 0.2242 0.8744 0.066 Uiso 1 1 calc R . . . .
C00V C 0.5301(4) 0.2531(3) 0.5426(2) 0.0502(10) Uani 1 1 d . . . . .
H00V H 0.5875 0.2203 0.5682 0.060 Uiso 1 1 calc R . . . .
C00W C 0.0578(3) 0.1998(3) 0.7981(3) 0.0508(10) Uani 1 1 d . . . . .
H00W H 0.0275 0.1401 0.7810 0.061 Uiso 1 1 calc R . . . .
C00X C 0.8017(3) 0.4055(3) 0.7349(2) 0.0464(9) Uani 1 1 d . . . . .
C00Y C 0.0494(3) 0.3395(4) 0.8785(2) 0.0504(10) Uani 1 1 d . . . . .
H00Y H 0.0122 0.3726 0.9162 0.061 Uiso 1 1 calc R . . . .
C00Z C 0.7443(4) 0.4405(4) 0.5673(2) 0.0549(10) Uani 1 1 d . . . . .
H00Z H 0.7705 0.3751 0.5697 0.066 Uiso 1 1 calc R . . . .
C010 C 0.4476(5) 0.3024(4) 0.4282(2) 0.0613(13) Uani 1 1 d . . . . .
H010 H 0.4494 0.3037 0.3775 0.074 Uiso 1 1 calc R . . . .
C011 C 0.3594(4) 0.3477(3) 0.4655(2) 0.0509(10) Uani 1 1 d . . . . .
H011 H 0.3017 0.3796 0.4397 0.061 Uiso 1 1 calc R . . . .
C012 C 0.6666(4) 0.6332(4) 0.5572(3) 0.0589(12) Uani 1 1 d . . . . .
H012 H 0.6398 0.6983 0.5539 0.071 Uiso 1 1 calc R . . . .
C013 C 0.0781(4) 0.5515(5) 0.4629(2) 0.0603(12) Uani 1 1 d . . . . .
H01A H 0.0077 0.5874 0.4684 0.090 Uiso 1 1 calc GR . . . .
H01B H 0.0620 0.4835 0.4501 0.090 Uiso 1 1 calc GR . . . .
H01C H 0.1228 0.5818 0.4250 0.090 Uiso 1 1 calc GR . . . .
C014 C 0.7539(5) 0.4948(5) 0.5023(2) 0.0693(15) Uani 1 1 d . . . . .
H014 H 0.7872 0.4649 0.4617 0.083 Uiso 1 1 calc R . . . .
C015 C 0.5328(5) 0.2554(4) 0.4668(3) 0.0672(14) Uani 1 1 d . . . . .
H015 H 0.5926 0.2250 0.4420 0.081 Uiso 1 1 calc R . . . .
C016 C 0.7158(4) 0.5897(5) 0.4974(2) 0.0667(15) Uani 1 1 d . . . . .
H016 H 0.7229 0.6249 0.4539 0.080 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
S001 O003 1.427(3) . ?
S001 O004 1.424(2) . ?
S001 N006 1.677(3) . ?
S001 C00O 1.756(3) . ?
S002 C00J 1.722(3) . ?
S002 C00T 1.743(4) . ?
F005 C00X 1.326(5) . ?
N006 C00C 1.497(4) . ?
N006 C00H 1.434(4) . ?
F007 C00X 1.302(6) . ?
N008 C00A 1.143(5) . ?
C009 C00H 1.439(4) . ?
C009 C00R 1.398(5) . ?
C009 C00T 1.413(5) . ?
C00A C00B 1.444(4) . ?
C00B C00C 1.513(4) . ?
C00B C00F 1.339(5) . ?
C00C H00C 0.9800 . ?
C00C C00E 1.580(4) . ?
C00D C00E 1.513(4) . ?
C00D C00M 1.389(5) . ?
C00D C00V 1.382(5) . ?
C00E H00E 0.9800 . ?
C00E C00J 1.496(4) . ?
C00F C00I 1.493(5) . ?
C00F C00X 1.514(5) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.385(5) . ?
C00G C00O 1.377(4) . ?
C00H C00J 1.350(5) . ?
C00I C00Q 1.389(6) . ?
C00I C00Z 1.381(5) . ?
F00K C00X 1.290(5) . ?
C00L H00L 0.9300 . ?
C00L C00S 1.392(5) . ?
C00M H00M 0.9300 . ?
C00M C011 1.385(5) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.399(5) . ?
C00N C00P 1.378(5) . ?
C00P H00P 0.9300 . ?
C00P C00S 1.395(5) . ?
C00Q H00Q 0.9300 . ?
C00Q C012 1.390(5) . ?
C00R H00R 0.9300 . ?
C00R C00Y 1.381(5) . ?
C00S C013 1.503(5) . ?
C00T C00W 1.405(5) . ?
C00U H00U 0.9300 . ?
C00U C00W 1.360(7) . ?
C00U C00Y 1.379(7) . ?
C00V H00V 0.9300 . ?
C00V C015 1.390(6) . ?
C00W H00W 0.9300 . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C00Z C014 1.401(7) . ?
C010 H010 0.9300 . ?
C010 C011 1.378(7) . ?
C010 C015 1.376(8) . ?
C011 H011 0.9300 . ?
C012 H012 0.9300 . ?
C012 C016 1.368(8) . ?
C013 H01A 0.9600 . ?
C013 H01B 0.9600 . ?
C013 H01C 0.9600 . ?
C014 H014 0.9300 . ?
C014 C016 1.351(8) . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O003 S001 N006 104.89(13) . . ?
O003 S001 C00O 109.73(15) . . ?
O004 S001 O003 119.60(15) . . ?
O004 S001 N006 107.20(14) . . ?
O004 S001 C00O 109.42(15) . . ?
N006 S001 C00O 104.91(13) . . ?
C00J S002 C00T 89.88(16) . . ?
C00C N006 S001 114.00(19) . . ?
C00H N006 S001 119.2(2) . . ?
C00H N006 C00C 106.9(2) . . ?
C00R C009 C00H 133.1(3) . . ?
C00R C009 C00T 118.4(3) . . ?
C00T C009 C00H 108.5(3) . . ?
N008 C00A C00B 176.2(4) . . ?
C00A C00B C00C 113.0(3) . . ?
C00F C00B C00A 122.2(3) . . ?
C00F C00B C00C 124.5(3) . . ?
N006 C00C C00B 110.3(2) . . ?
N006 C00C H00C 109.7 . . ?
N006 C00C C00E 107.3(2) . . ?
C00B C00C H00C 109.7 . . ?
C00B C00C C00E 110.2(2) . . ?
C00E C00C H00C 109.7 . . ?
C00M C00D C00E 120.8(3) . . ?
C00V C00D C00E 120.3(3) . . ?
C00V C00D C00M 119.0(3) . . ?
C00C C00E H00E 108.6 . . ?
C00D C00E C00C 113.3(2) . . ?
C00D C00E H00E 108.6 . . ?
C00J C00E C00C 100.3(2) . . ?
C00J C00E C00D 117.0(3) . . ?
C00J C00E H00E 108.6 . . ?
C00B C00F C00I 124.7(3) . . ?
C00B C00F C00X 119.4(3) . . ?
C00I C00F C00X 115.9(3) . . ?
C00L C00G H00G 120.3 . . ?
C00O C00G H00G 120.3 . . ?
C00O C00G C00L 119.4(3) . . ?
N006 C00H C009 134.4(3) . . ?
C00J C00H N006 111.1(3) . . ?
C00J C00H C009 114.4(3) . . ?
C00Q C00I C00F 119.5(3) . . ?
C00Z C00I C00F 121.5(4) . . ?
C00Z C00I C00Q 119.0(4) . . ?
C00E C00J S002 131.9(2) . . ?
C00H C00J S002 113.6(2) . . ?
C00H C00J C00E 114.2(3) . . ?
C00G C00L H00L 119.5 . . ?
C00G C00L C00S 121.0(3) . . ?
C00S C00L H00L 119.5 . . ?
C00D C00M H00M 119.8 . . ?
C011 C00M C00D 120.3(4) . . ?
C011 C00M H00M 119.8 . . ?
C00O C00N H00N 120.4 . . ?
C00P C00N H00N 120.4 . . ?
C00P C00N C00O 119.1(3) . . ?
C00G C00O S001 120.4(3) . . ?
C00G C00O C00N 120.8(3) . . ?
C00N C00O S001 118.7(2) . . ?
C00N C00P H00P 119.5 . . ?
C00N C00P C00S 121.0(3) . . ?
C00S C00P H00P 119.5 . . ?
C00I C00Q H00Q 120.2 . . ?
C00I C00Q C012 119.6(4) . . ?
C012 C00Q H00Q 120.2 . . ?
C009 C00R H00R 120.3 . . ?
C00Y C00R C009 119.4(4) . . ?
C00Y C00R H00R 120.3 . . ?
C00L C00S C00P 118.7(3) . . ?
C00L C00S C013 121.3(4) . . ?
C00P C00S C013 120.0(4) . . ?
C009 C00T S002 113.6(3) . . ?
C00W C00T S002 125.4(3) . . ?
C00W C00T C009 121.0(4) . . ?
C00W C00U H00U 119.5 . . ?
C00W C00U C00Y 121.0(4) . . ?
C00Y C00U H00U 119.5 . . ?
C00D C00V H00V 119.8 . . ?
C00D C00V C015 120.3(4) . . ?
C015 C00V H00V 119.8 . . ?
C00T C00W H00W 120.6 . . ?
C00U C00W C00T 118.8(4) . . ?
C00U C00W H00W 120.6 . . ?
F005 C00X C00F 112.7(3) . . ?
F007 C00X F005 106.6(4) . . ?
F007 C00X C00F 110.9(3) . . ?
F00K C00X F005 104.3(4) . . ?
F00K C00X F007 109.0(5) . . ?
F00K C00X C00F 113.0(3) . . ?
C00R C00Y H00Y 119.3 . . ?
C00U C00Y C00R 121.4(4) . . ?
C00U C00Y H00Y 119.3 . . ?
C00I C00Z H00Z 120.1 . . ?
C00I C00Z C014 119.7(5) . . ?
C014 C00Z H00Z 120.1 . . ?
C011 C010 H010 120.3 . . ?
C015 C010 H010 120.3 . . ?
C015 C010 C011 119.4(4) . . ?
C00M C011 H011 119.8 . . ?
C010 C011 C00M 120.5(4) . . ?
C010 C011 H011 119.8 . . ?
C00Q C012 H012 119.4 . . ?
C016 C012 C00Q 121.3(5) . . ?
C016 C012 H012 119.4 . . ?
C00S C013 H01A 109.5 . . ?
C00S C013 H01B 109.5 . . ?
C00S C013 H01C 109.5 . . ?
H01A C013 H01B 109.5 . . ?
H01A C013 H01C 109.5 . . ?
H01B C013 H01C 109.5 . . ?
C00Z C014 H014 119.4 . . ?
C016 C014 C00Z 121.2(5) . . ?
C016 C014 H014 119.4 . . ?
C00V C015 H015 119.8 . . ?
C010 C015 C00V 120.5(4) . . ?
C010 C015 H015 119.8 . . ?
C012 C016 H016 120.4 . . ?
C014 C016 C012 119.2(4) . . ?
C014 C016 H016 120.4 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2018-12-29
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.805
####################################################################### 
# 
# 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_8a
_database_code_depnum_ccdc_archive 'CCDC 2088344'
loop_
_audit_author_name
_audit_author_address
'Ying-Chun Chen'
;Sichuan University
China
;
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2021-08-09 downloaded from the CCDC.
;
_audit_creation_date             2021-03-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H22 F3 N3 O2 S3'
_chemical_formula_sum            'C34 H22 F3 N3 O2 S3'
_chemical_formula_weight         657.72
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.6266(7)
_cell_length_b                   18.4175(16)
_cell_length_c                   19.2928(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3065.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5492
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      22.007
_cell_measurement_theta_min      2.384
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1354 before and 0.0782 after correction.
The Ratio of minimum to maximum transmission is 0.7162.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_unetI/netI     0.0992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25772
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.111
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3862
_reflns_number_total             7055
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         7055
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.006
_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)+(0.0578P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1485
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00I(H00I)
2.b Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00X(H00X), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018)
2.c Idealised Me refined as rotating group:
 C019(H01A,H01B,H01C)
;
_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 0.14357(18) 0.44371(10) 0.36906(8) 0.0576(4) Uani 1 1 d . . . . .
S002 S 0.66994(17) 0.41720(9) 0.48670(9) 0.0587(4) Uani 1 1 d . . . . .
S003 S 0.5608(2) 0.50959(10) 0.69513(9) 0.0645(5) Uani 1 1 d . . . . .
F004 F 0.2376(4) 0.63538(18) 0.5591(2) 0.0701(11) Uani 1 1 d . . . . .
F005 F 0.4394(4) 0.63496(17) 0.6237(2) 0.0649(10) Uani 1 1 d . . . . .
F006 F 0.2244(4) 0.5967(2) 0.6632(2) 0.0708(11) Uani 1 1 d . . . . .
O007 O 0.2219(5) 0.3965(2) 0.3219(2) 0.0682(13) Uani 1 1 d . . . . .
O008 O -0.0186(5) 0.4387(3) 0.3802(2) 0.0775(14) Uani 1 1 d . . . . .
N009 N 0.4213(6) 0.4045(3) 0.6314(2) 0.0506(12) Uani 1 1 d . . . . .
N00A N 0.2245(5) 0.4279(2) 0.4477(2) 0.0463(12) Uani 1 1 d . . . . .
C00B C 0.3498(6) 0.5207(3) 0.5798(3) 0.0391(12) Uani 1 1 d . . . . .
C00C C 0.1931(6) 0.4845(3) 0.5632(3) 0.0398(12) Uani 1 1 d . . . . .
C00D C 0.4874(6) 0.4554(3) 0.4815(3) 0.0411(13) Uani 1 1 d . . . . .
C00E C 0.3858(6) 0.4101(3) 0.4527(3) 0.0424(13) Uani 1 1 d . . . . .
C00F C 0.4339(6) 0.4751(3) 0.6327(3) 0.0422(13) Uani 1 1 d . . . . .
C00G C 0.4467(7) 0.3398(3) 0.4338(3) 0.0490(14) Uani 1 1 d . . . . .
N00H N -0.0179(6) 0.4807(3) 0.6573(3) 0.0683(16) Uani 1 1 d . . . . .
C00I C 0.4442(6) 0.5289(3) 0.5088(3) 0.0394(12) Uani 1 1 d . . . . .
H00I H 0.3682 0.5476 0.4756 0.047 Uiso 1 1 calc R U . . .
C00J C 0.5765(6) 0.5835(3) 0.5069(3) 0.0433(13) Uani 1 1 d . . . . .
C00K C 0.6044(7) 0.3377(3) 0.4493(3) 0.0528(16) Uani 1 1 d . . . . .
C00L C 0.3129(7) 0.5963(3) 0.6065(3) 0.0502(15) Uani 1 1 d . . . . .
C00M C 0.7148(6) 0.5747(3) 0.5425(3) 0.0532(16) Uani 1 1 d . . . . .
H00M H 0.7295 0.5340 0.5702 0.064 Uiso 1 1 calc R U . . .
C00N C 0.1917(7) 0.5334(3) 0.3498(3) 0.0542(16) Uani 1 1 d . . . . .
C00O C 0.5175(7) 0.3733(4) 0.6811(3) 0.0546(16) Uani 1 1 d . . . . .
C00P C 0.0775(6) 0.4839(3) 0.6171(3) 0.0491(14) Uani 1 1 d . . . . .
C00Q C 0.5586(8) 0.6442(3) 0.4655(3) 0.0508(15) Uani 1 1 d . . . . .
H00Q H 0.4673 0.6505 0.4405 0.061 Uiso 1 1 calc R U . . .
C00R C 0.1417(6) 0.4518(3) 0.5052(3) 0.0450(13) Uani 1 1 d . . . . .
H00R H 0.0352 0.4440 0.5033 0.054 Uiso 1 1 calc R U . . .
C00S C 0.3740(9) 0.2783(3) 0.4064(3) 0.0619(18) Uani 1 1 d . . . . .
H00S H 0.2680 0.2784 0.3975 0.074 Uiso 1 1 calc R U . . .
C00T C 0.8310(7) 0.6260(4) 0.5370(4) 0.0658(19) Uani 1 1 d . . . . .
H00T H 0.9234 0.6196 0.5610 0.079 Uiso 1 1 calc R U . . .
C00U C 0.6730(9) 0.6952(4) 0.4607(4) 0.0669(19) Uani 1 1 d . . . . .
H00U H 0.6579 0.7362 0.4334 0.080 Uiso 1 1 calc R U . . .
C00V C 0.3136(7) 0.5476(4) 0.3038(3) 0.0620(17) Uani 1 1 d . . . . .
H00V H 0.3704 0.5099 0.2841 0.074 Uiso 1 1 calc R U . . .
C00W C 0.6027(6) 0.4224(4) 0.7200(3) 0.0591(17) Uani 1 1 d . . . . .
C00X C 0.6918(9) 0.2758(4) 0.4350(4) 0.071(2) Uani 1 1 d . . . . .
H00X H 0.7975 0.2750 0.4445 0.086 Uiso 1 1 calc R U . . .
C00Y C 0.2682(9) 0.6759(4) 0.3175(4) 0.0681(19) Uani 1 1 d . . . . .
C00Z C 0.3467(9) 0.6191(4) 0.2886(4) 0.0670(18) Uani 1 1 d . . . . .
H00Z H 0.4258 0.6290 0.2572 0.080 Uiso 1 1 calc R U . . .
C010 C 0.8110(8) 0.6864(4) 0.4962(4) 0.069(2) Uani 1 1 d . . . . .
H010 H 0.8892 0.7210 0.4925 0.083 Uiso 1 1 calc R U . . .
C011 C 0.1123(7) 0.5899(4) 0.3799(3) 0.0647(18) Uani 1 1 d . . . . .
H011 H 0.0325 0.5807 0.4111 0.078 Uiso 1 1 calc R U . . .
C012 C 0.4618(10) 0.2180(4) 0.3930(4) 0.072(2) Uani 1 1 d . . . . .
H012 H 0.4147 0.1771 0.3741 0.087 Uiso 1 1 calc R U . . .
C013 C 0.5339(9) 0.2997(4) 0.6914(4) 0.073(2) Uani 1 1 d . . . . .
H013 H 0.4757 0.2669 0.6655 0.088 Uiso 1 1 calc R U . . .
C014 C 0.1524(9) 0.6611(4) 0.3631(4) 0.072(2) Uani 1 1 d . . . . .
H014 H 0.0988 0.6993 0.3836 0.086 Uiso 1 1 calc R U . . .
C015 C 0.6207(10) 0.2166(4) 0.4069(4) 0.075(2) Uani 1 1 d . . . . .
H015 H 0.6782 0.1752 0.3970 0.090 Uiso 1 1 calc R U . . .
C016 C 0.7207(10) 0.3250(6) 0.7789(4) 0.094(3) Uani 1 1 d . . . . .
H016 H 0.7898 0.3074 0.8118 0.113 Uiso 1 1 calc R U . . .
C017 C 0.6368(11) 0.2753(5) 0.7401(4) 0.090(3) Uani 1 1 d . . . . .
H017 H 0.6504 0.2257 0.7471 0.109 Uiso 1 1 calc R U . . .
C018 C 0.7071(8) 0.3985(6) 0.7712(4) 0.082(2) Uani 1 1 d . . . . .
H018 H 0.7636 0.4308 0.7982 0.099 Uiso 1 1 calc R U . . .
C019 C 0.3087(12) 0.7534(4) 0.2990(5) 0.100(3) Uani 1 1 d . . . . .
H01A H 0.4123 0.7639 0.3141 0.151 Uiso 1 1 calc R U . . .
H01B H 0.2375 0.7858 0.3214 0.151 Uiso 1 1 calc R U . . .
H01C H 0.3020 0.7596 0.2497 0.151 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O007 1.428(4) . ?
S001 O008 1.418(4) . ?
S001 N00A 1.695(5) . ?
S001 C00N 1.742(7) . ?
S002 C00D 1.728(5) . ?
S002 C00K 1.727(6) . ?
S003 C00F 1.747(5) . ?
S003 C00W 1.715(7) . ?
F004 C00L 1.333(7) . ?
F005 C00L 1.345(7) . ?
F006 C00L 1.333(6) . ?
N009 C00F 1.304(7) . ?
N009 C00O 1.392(7) . ?
N00A C00E 1.433(7) . ?
N00A C00R 1.390(7) . ?
C00B C00C 1.540(7) . ?
C00B C00F 1.509(7) . ?
C00B C00I 1.600(7) . ?
C00B C00L 1.517(8) . ?
C00C C00P 1.439(8) . ?
C00C C00R 1.347(7) . ?
C00D C00E 1.332(7) . ?
C00D C00I 1.500(7) . ?
C00E C00G 1.444(7) . ?
C00G C00K 1.393(8) . ?
C00G C00S 1.398(8) . ?
N00H C00P 1.133(7) . ?
C00I H00I 0.9800 . ?
C00I C00J 1.521(7) . ?
C00J C00M 1.386(8) . ?
C00J C00Q 1.383(7) . ?
C00K C00X 1.395(8) . ?
C00M H00M 0.9300 . ?
C00M C00T 1.382(8) . ?
C00N C00V 1.400(9) . ?
C00N C011 1.375(8) . ?
C00O C00W 1.385(8) . ?
C00O C013 1.378(9) . ?
C00Q H00Q 0.9300 . ?
C00Q C00U 1.365(8) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00S C012 1.370(9) . ?
C00T H00T 0.9300 . ?
C00T C010 1.374(10) . ?
C00U H00U 0.9300 . ?
C00U C010 1.382(10) . ?
C00V H00V 0.9300 . ?
C00V C00Z 1.379(9) . ?
C00W C018 1.407(9) . ?
C00X H00X 0.9300 . ?
C00X C015 1.363(10) . ?
C00Y C00Z 1.367(9) . ?
C00Y C014 1.359(10) . ?
C00Y C019 1.511(10) . ?
C00Z H00Z 0.9300 . ?
C010 H010 0.9300 . ?
C011 H011 0.9300 . ?
C011 C014 1.394(9) . ?
C012 H012 0.9300 . ?
C012 C015 1.397(11) . ?
C013 H013 0.9300 . ?
C013 C017 1.369(10) . ?
C014 H014 0.9300 . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C016 C017 1.386(12) . ?
C016 C018 1.367(12) . ?
C017 H017 0.9300 . ?
C018 H018 0.9300 . ?
C019 H01A 0.9600 . ?
C019 H01B 0.9600 . ?
C019 H01C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O007 S001 N00A 105.7(3) . . ?
O007 S001 C00N 109.1(3) . . ?
O008 S001 O007 121.6(3) . . ?
O008 S001 N00A 105.0(3) . . ?
O008 S001 C00N 109.2(3) . . ?
N00A S001 C00N 104.8(3) . . ?
C00K S002 C00D 91.3(3) . . ?
C00W S003 C00F 89.1(3) . . ?
C00F N009 C00O 110.3(5) . . ?
C00E N00A S001 119.9(4) . . ?
C00R N00A S001 116.6(4) . . ?
C00R N00A C00E 121.2(4) . . ?
C00C C00B C00I 108.1(4) . . ?
C00F C00B C00C 108.7(4) . . ?
C00F C00B C00I 112.7(4) . . ?
C00F C00B C00L 112.4(5) . . ?
C00L C00B C00C 106.5(4) . . ?
C00L C00B C00I 108.2(4) . . ?
C00P C00C C00B 117.5(5) . . ?
C00R C00C C00B 130.9(5) . . ?
C00R C00C C00P 111.6(5) . . ?
C00E C00D S002 111.7(4) . . ?
C00E C00D C00I 123.3(5) . . ?
C00I C00D S002 125.0(4) . . ?
N00A C00E C00G 122.8(5) . . ?
C00D C00E N00A 121.6(5) . . ?
C00D C00E C00G 115.3(5) . . ?
N009 C00F S003 115.4(4) . . ?
N009 C00F C00B 120.1(5) . . ?
C00B C00F S003 124.4(4) . . ?
C00K C00G C00E 109.0(5) . . ?
C00K C00G C00S 119.8(6) . . ?
C00S C00G C00E 131.1(6) . . ?
C00B C00I H00I 104.6 . . ?
C00D C00I C00B 110.0(4) . . ?
C00D C00I H00I 104.6 . . ?
C00D C00I C00J 113.7(4) . . ?
C00J C00I C00B 117.7(4) . . ?
C00J C00I H00I 104.7 . . ?
C00M C00J C00I 123.8(5) . . ?
C00Q C00J C00I 117.7(5) . . ?
C00Q C00J C00M 118.4(5) . . ?
C00G C00K S002 112.7(4) . . ?
C00G C00K C00X 120.5(6) . . ?
C00X C00K S002 126.7(5) . . ?
F004 C00L F005 106.1(5) . . ?
F004 C00L C00B 111.3(5) . . ?
F005 C00L C00B 113.5(4) . . ?
F006 C00L F004 106.3(5) . . ?
F006 C00L F005 105.0(5) . . ?
F006 C00L C00B 113.9(5) . . ?
C00J C00M H00M 119.8 . . ?
C00T C00M C00J 120.5(6) . . ?
C00T C00M H00M 119.8 . . ?
C00V C00N S001 119.4(5) . . ?
C011 C00N S001 120.6(5) . . ?
C011 C00N C00V 120.0(6) . . ?
C00W C00O N009 114.9(5) . . ?
C013 C00O N009 124.5(6) . . ?
C013 C00O C00W 120.6(6) . . ?
N00H C00P C00C 176.2(7) . . ?
C00J C00Q H00Q 119.5 . . ?
C00U C00Q C00J 121.0(6) . . ?
C00U C00Q H00Q 119.5 . . ?
N00A C00R H00R 115.3 . . ?
C00C C00R N00A 129.4(5) . . ?
C00C C00R H00R 115.3 . . ?
C00G C00S H00S 120.7 . . ?
C012 C00S C00G 118.7(7) . . ?
C012 C00S H00S 120.7 . . ?
C00M C00T H00T 119.8 . . ?
C010 C00T C00M 120.4(6) . . ?
C010 C00T H00T 119.8 . . ?
C00Q C00U H00U 119.7 . . ?
C00Q C00U C010 120.6(6) . . ?
C010 C00U H00U 119.7 . . ?
C00N C00V H00V 121.0 . . ?
C00Z C00V C00N 118.0(6) . . ?
C00Z C00V H00V 121.0 . . ?
C00O C00W S003 110.3(4) . . ?
C00O C00W C018 121.0(7) . . ?
C018 C00W S003 128.6(6) . . ?
C00K C00X H00X 120.4 . . ?
C015 C00X C00K 119.3(7) . . ?
C015 C00X H00X 120.4 . . ?
C00Z C00Y C019 120.8(8) . . ?
C014 C00Y C00Z 118.3(7) . . ?
C014 C00Y C019 120.9(7) . . ?
C00V C00Z H00Z 118.6 . . ?
C00Y C00Z C00V 122.9(7) . . ?
C00Y C00Z H00Z 118.6 . . ?
C00T C010 C00U 119.1(6) . . ?
C00T C010 H010 120.4 . . ?
C00U C010 H010 120.4 . . ?
C00N C011 H011 120.3 . . ?
C00N C011 C014 119.4(7) . . ?
C014 C011 H011 120.3 . . ?
C00S C012 H012 119.3 . . ?
C00S C012 C015 121.4(7) . . ?
C015 C012 H012 119.3 . . ?
C00O C013 H013 120.4 . . ?
C017 C013 C00O 119.2(8) . . ?
C017 C013 H013 120.4 . . ?
C00Y C014 C011 121.5(7) . . ?
C00Y C014 H014 119.3 . . ?
C011 C014 H014 119.3 . . ?
C00X C015 C012 120.2(7) . . ?
C00X C015 H015 119.9 . . ?
C012 C015 H015 119.9 . . ?
C017 C016 H016 118.3 . . ?
C018 C016 H016 118.3 . . ?
C018 C016 C017 123.4(8) . . ?
C013 C017 C016 119.5(8) . . ?
C013 C017 H017 120.2 . . ?
C016 C017 H017 120.2 . . ?
C00W C018 H018 121.9 . . ?
C016 C018 C00W 116.2(8) . . ?
C016 C018 H018 121.9 . . ?
C00Y C019 H01A 109.5 . . ?
C00Y C019 H01B 109.5 . . ?
C00Y C019 H01C 109.5 . . ?
H01A C019 H01B 109.5 . . ?
H01A C019 H01C 109.5 . . ?
H01B C019 H01C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S001 N00A C00E C00D 112.0(5) . . . . ?
S001 N00A C00E C00G -74.7(6) . . . . ?
S001 N00A C00R C00C -138.6(5) . . . . ?
S001 C00N C00V C00Z 178.7(5) . . . . ?
S001 C00N C011 C014 -179.5(5) . . . . ?
S002 C00D C00E N00A 175.3(4) . . . . ?
S002 C00D C00E C00G 1.4(6) . . . . ?
S002 C00D C00I C00B -103.6(5) . . . . ?
S002 C00D C00I C00J 30.9(6) . . . . ?
S002 C00K C00X C015 178.1(6) . . . . ?
S003 C00W C018 C016 -178.2(6) . . . . ?
O007 S001 N00A C00E 34.0(5) . . . . ?
O007 S001 N00A C00R -162.8(4) . . . . ?
O007 S001 C00N C00V -11.6(6) . . . . ?
O007 S001 C00N C011 169.1(5) . . . . ?
O008 S001 N00A C00E 163.7(4) . . . . ?
O008 S001 N00A C00R -33.1(5) . . . . ?
O008 S001 C00N C00V -146.6(5) . . . . ?
O008 S001 C00N C011 34.1(6) . . . . ?
N009 C00O C00W S003 0.8(7) . . . . ?
N009 C00O C00W C018 -178.7(6) . . . . ?
N009 C00O C013 C017 177.4(6) . . . . ?
N00A S001 C00N C00V 101.3(5) . . . . ?
N00A S001 C00N C011 -78.0(5) . . . . ?
N00A C00E C00G C00K -175.6(5) . . . . ?
N00A C00E C00G C00S 2.5(10) . . . . ?
C00B C00C C00R N00A 14.6(10) . . . . ?
C00B C00I C00J C00M 69.7(7) . . . . ?
C00B C00I C00J C00Q -112.2(5) . . . . ?
C00C C00B C00F S003 -148.8(4) . . . . ?
C00C C00B C00F N009 35.1(7) . . . . ?
C00C C00B C00I C00D -66.8(5) . . . . ?
C00C C00B C00I C00J 160.8(4) . . . . ?
C00C C00B C00L F004 -60.6(6) . . . . ?
C00C C00B C00L F005 179.7(5) . . . . ?
C00C C00B C00L F006 59.5(6) . . . . ?
C00D S002 C00K C00G -0.7(5) . . . . ?
C00D S002 C00K C00X 179.9(6) . . . . ?
C00D C00E C00G C00K -1.9(7) . . . . ?
C00D C00E C00G C00S 176.2(6) . . . . ?
C00D C00I C00J C00M -61.1(7) . . . . ?
C00D C00I C00J C00Q 117.0(6) . . . . ?
C00E N00A C00R C00C 24.3(9) . . . . ?
C00E C00D C00I C00B 73.4(6) . . . . ?
C00E C00D C00I C00J -152.1(5) . . . . ?
C00E C00G C00K S002 1.5(7) . . . . ?
C00E C00G C00K C00X -179.0(6) . . . . ?
C00E C00G C00S C012 179.7(6) . . . . ?
C00F S003 C00W C00O -1.1(5) . . . . ?
C00F S003 C00W C018 178.4(6) . . . . ?
C00F N009 C00O C00W 0.2(7) . . . . ?
C00F N009 C00O C013 -178.1(6) . . . . ?
C00F C00B C00C C00P 68.5(6) . . . . ?
C00F C00B C00C C00R -111.4(6) . . . . ?
C00F C00B C00I C00D 53.4(6) . . . . ?
C00F C00B C00I C00J -79.0(5) . . . . ?
C00F C00B C00L F004 -179.5(4) . . . . ?
C00F C00B C00L F005 60.7(6) . . . . ?
C00F C00B C00L F006 -59.4(6) . . . . ?
C00G C00K C00X C015 -1.3(10) . . . . ?
C00G C00S C012 C015 0.9(11) . . . . ?
C00I C00B C00C C00P -168.8(5) . . . . ?
C00I C00B C00C C00R 11.2(7) . . . . ?
C00I C00B C00F S003 91.4(5) . . . . ?
C00I C00B C00F N009 -84.7(6) . . . . ?
C00I C00B C00L F004 55.3(6) . . . . ?
C00I C00B C00L F005 -64.4(6) . . . . ?
C00I C00B C00L F006 175.5(4) . . . . ?
C00I C00D C00E N00A -2.0(8) . . . . ?
C00I C00D C00E C00G -175.9(5) . . . . ?
C00I C00J C00M C00T 178.6(5) . . . . ?
C00I C00J C00Q C00U -179.4(5) . . . . ?
C00J C00M C00T C010 0.0(10) . . . . ?
C00J C00Q C00U C010 1.4(10) . . . . ?
C00K S002 C00D C00E -0.4(5) . . . . ?
C00K S002 C00D C00I 176.8(5) . . . . ?
C00K C00G C00S C012 -2.4(10) . . . . ?
C00K C00X C015 C012 -0.3(11) . . . . ?
C00L C00B C00C C00P -52.8(6) . . . . ?
C00L C00B C00C C00R 127.2(6) . . . . ?
C00L C00B C00F S003 -31.2(6) . . . . ?
C00L C00B C00F N009 152.8(5) . . . . ?
C00L C00B C00I C00D 178.3(4) . . . . ?
C00L C00B C00I C00J 45.9(6) . . . . ?
C00M C00J C00Q C00U -1.3(9) . . . . ?
C00M C00T C010 C00U 0.0(10) . . . . ?
C00N S001 N00A C00E -81.3(5) . . . . ?
C00N S001 N00A C00R 81.9(4) . . . . ?
C00N C00V C00Z C00Y 1.5(10) . . . . ?
C00N C011 C014 C00Y 0.2(10) . . . . ?
C00O N009 C00F S003 -1.0(6) . . . . ?
C00O N009 C00F C00B 175.3(5) . . . . ?
C00O C00W C018 C016 1.2(10) . . . . ?
C00O C013 C017 C016 1.0(11) . . . . ?
C00P C00C C00R N00A -165.4(5) . . . . ?
C00Q C00J C00M C00T 0.6(9) . . . . ?
C00Q C00U C010 C00T -0.7(10) . . . . ?
C00R N00A C00E C00D -50.4(7) . . . . ?
C00R N00A C00E C00G 122.9(6) . . . . ?
C00S C00G C00K S002 -176.9(5) . . . . ?
C00S C00G C00K C00X 2.6(10) . . . . ?
C00S C012 C015 C00X 0.5(12) . . . . ?
C00V C00N C011 C014 1.2(9) . . . . ?
C00W S003 C00F N009 1.2(5) . . . . ?
C00W S003 C00F C00B -174.9(5) . . . . ?
C00W C00O C013 C017 -0.7(10) . . . . ?
C00Z C00Y C014 C011 -0.7(11) . . . . ?
C011 C00N C00V C00Z -2.0(9) . . . . ?
C013 C00O C00W S003 179.1(5) . . . . ?
C013 C00O C00W C018 -0.5(10) . . . . ?
C014 C00Y C00Z C00V -0.2(11) . . . . ?
C017 C016 C018 C00W -0.9(12) . . . . ?
C018 C016 C017 C013 -0.2(13) . . . . ?
C019 C00Y C00Z C00V -179.8(7) . . . . ?
C019 C00Y C014 C011 179.0(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
