# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_202405199b_auto
_database_code_depnum_ccdc_archive 'CCDC 2360355'
loop_
_audit_author_name
_audit_author_address
Liupan
;Zhengzhou University
China
;
_audit_update_record             
;
2024-06-04 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2024-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 F3 N2 S'
_chemical_formula_sum            'C13 H13 F3 N2 S'
_chemical_formula_weight         286.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H2N1O4S1F2
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'
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                   6.5464(4)
_cell_length_b                   13.7584(8)
_cell_length_c                   16.2007(10)
_cell_angle_alpha                67.284(6)
_cell_angle_beta                 85.636(5)
_cell_angle_gamma                87.696(5)
_cell_volume                     1341.98(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2645
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7140
_cell_measurement_theta_min      3.5960
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.688
_exptl_absorpt_coefficient_mu    2.381
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9426
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.483
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_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    -56.00  37.00   1.00    1.00    --  -33.50  37.00 -60.00   93
  2  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 126.00   93
  3  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00  60.00   87
  4  ω     18.00 105.00   1.00    1.00    --   36.47  57.00   0.00   87
  5  ω    -18.00  65.00   1.00    1.00    --   36.47 -77.00   0.00   83
  6  ω    -30.00  -4.00   1.00    1.00    --   36.47 -57.00-150.00   26
  7  ω    -12.00  15.00   1.00    1.00    --   36.47 -37.00-150.00   27
  8  ω     67.00 110.00   1.00    1.00    --   36.47 178.00-180.00   43
  9  ω     38.00  64.00   1.00    1.00    --   36.47 -99.00  30.00   26
 10  ω     -5.00  21.00   1.00    1.00    --   36.47 -77.00-150.00   26
 11  ω     34.00  59.00   1.00    1.00    --   36.47 -37.00-150.00   25
 12  ω     37.00  73.00   1.00    1.00    --   36.47 -99.00-120.00   36
 13  ω      6.00  34.00   1.00    1.00    --   36.47 -99.00  30.00   28
 14  ω      7.00  74.00   1.00    1.00    --   36.47 -99.00 120.00   67
 15  ω      6.00  55.00   1.00    1.00    --   36.47 -57.00-150.00   49
 16  ω     55.00  98.00   1.00    7.50    --  108.00 -94.00-180.00   43
 17  ω     37.00  92.00   1.00    7.50    --  108.00 -30.00 -30.00   55
 18  ω    149.00 176.00   1.00    7.50    --  108.00  61.00-150.00   27
 19  ω     38.00 128.00   1.00    7.50    --  108.00 -45.00-120.00   90
 20  ω     52.00 123.00   1.00    7.50    --  108.00 -61.00 -60.00   71
 21  ω     92.00 124.00   1.00    7.50    --  108.00  61.00-150.00   32
 22  ω     74.00 100.00   1.00    7.50    --  108.00-111.00  90.00   26
 23  ω     41.00 108.00   1.00    7.50    --  108.00-111.00 120.00   67
 24  ω     62.00 117.00   1.00    7.50    --  108.00 178.00 -60.00   55
 25  ω    113.00 169.00   1.00    7.50    --  108.00  77.00  30.00   56
 26  ω     48.00  74.00   1.00    7.50    --  108.00-111.00 -30.00   26
 27  ω     42.00 119.00   1.00    7.50    --  108.00 -45.00  60.00   77
 28  ω     66.00 104.00   1.00    7.50    --  108.00 -94.00 -30.00   38
 29  ω     45.00  71.00   1.00    7.50    --  108.00 -61.00  60.00   26
 30  ω     42.00 109.00   1.00    7.50    --  108.00-111.00 -90.00   67
 31  ω     41.00 173.00   1.00    7.50    --  108.00   0.00   0.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1768513000
_diffrn_orient_matrix_UB_12      -0.0421558000
_diffrn_orient_matrix_UB_13      -0.0457434000
_diffrn_orient_matrix_UB_21      -0.1523465000
_diffrn_orient_matrix_UB_22      -0.0677461000
_diffrn_orient_matrix_UB_23      -0.0219021000
_diffrn_orient_matrix_UB_31      -0.0350024000
_diffrn_orient_matrix_UB_32      0.0914902000
_diffrn_orient_matrix_UB_33      -0.0900064000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3273
_reflns_number_total             4763
_reflns_odcompleteness_completeness 99.79
_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 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_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         0.679
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         4763
_refine_ls_number_restraints     113
_refine_ls_R_factor_all          0.1330
_refine_ls_R_factor_gt           0.1078
_refine_ls_restrained_S_all      1.283
_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)+(0.2300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3296
_refine_ls_wR_factor_ref         0.3717
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C10'-C9'
 1.64 with sigma of 0.02
 C10'-C11'
 1.64 with sigma of 0.02
 C10B-C11'
 1.54 with sigma of 0.02
 C9'A-C10B
 1.54 with sigma of 0.02
 S1'A-C13B
 1.78 with sigma of 0.02
 F2'A-S1'A
 2.5 with sigma of 0.02
 C11A-C10A
 1.54 with sigma of 0.02
 S1A-C12A
 1.78 with sigma of 0.02
 C8A-C12A
 1.54 with sigma of 0.02
 C10-C9
 1.54 with sigma of 0.02
 C9A-C8A
 1.54 with sigma of 0.02
 C10A-C9A
 1.54 with sigma of 0.02
 S1A-F2A
 2.2 with sigma of 0.02
 S1A-F3A
 2.3 with sigma of 0.02
 C11A-N2
 1.45 with sigma of 0.02
 S1'A-F3'A
 2.3 with sigma of 0.02
 S1'A-F1'A
 2.3 with sigma of 0.02
 F3A-F2A
 1.8 with sigma of 0.02
 F3A-F1A
 1.8 with sigma of 0.02
 C13B-F1'A = C13B-F3'A = C13B-F2'A
 1.35 with sigma of 0.02
 C13A-F3A
 1.35 with sigma of 0.02
 C8'-C12'
 1.68 with sigma of 0.02
 C8'A-C12B
 1.54 with sigma of 0.02
 C9'-C8'
 1.78 with sigma of 0.02
 C9'A-C8'A
 1.54 with sigma of 0.02
 S1'-C12'
 1.78 with sigma of 0.02
 C7'-C8'A
 1.54 with sigma of 0.02
 F3'-F1' \\sim F3'-F2' \\sim F1'-F2'
 with sigma of 0.04
 C13'-F3' \\sim C13'-F1' \\sim C13'-F2'
 with sigma of 0.02
 F1'A-F3'A \\sim F1'A-F2'A \\sim F3'A-F2'A
 with sigma of 0.04
 C13B-F1'A \\sim C13B-F3'A \\sim C13B-F2'A
 with sigma of 0.02
 F3A-F2A \\sim F3A-F1A \\sim F2A-F1A
 with sigma of 0.04
 C13A-F3A \\sim C13A-F2A \\sim C13A-F1A
 with sigma of 0.02
 F1-F2 \\sim F1-F3 \\sim F2-F3
 with sigma of 0.04
 C13-F1 \\sim C13-F2 \\sim C13-F3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C10B) \\sim Ueq, Uanis(C10') \\sim Ueq, Uanis(C9'A) \\sim Ueq, Uanis(C9')
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2'A) \\sim Ueq, Uanis(F2') \\sim Ueq, Uanis(F3') \\sim Ueq, Uanis(F3'A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C8') \\sim Ueq, Uanis(C8'A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C10') = Uanis(C10B)
Uanis(C9') = Uanis(C9'A)
Uanis(C8') = Uanis(C8'A)
Uanis(C12') = Uanis(C12B)
Uanis(S1') = Uanis(S1'A)
Uanis(C13') = Uanis(C13B)
Uanis(F1') = Uanis(F1'A)
Uanis(F3') = Uanis(F3'A)
Uanis(F2') = Uanis(F2'A)
Uanis(C11) = Uanis(C11A)
Uanis(C10) = Uanis(C10A)
Uanis(C9) = Uanis(C9A)
Uanis(C8) = Uanis(C8A)
Uanis(C12) = Uanis(C12A)
Uanis(S1) = Uanis(S1A)
Uanis(C13) = Uanis(C13A)
Uanis(F3) = Uanis(F3A)
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
4. Others
 Sof(S1'A)=Sof(F1'A)=Sof(F2'A)=Sof(F3'A)=Sof(C8'A)=Sof(H8'A)=Sof(C9'A)=
 Sof(H9'C)=Sof(H9'D)=Sof(C10B)=Sof(H10G)=Sof(H10H)=Sof(H11G)=Sof(H11H)=
 Sof(C12B)=Sof(H12G)=Sof(H12H)=Sof(C13B)=1-FVAR(1)
 Sof(S1')=Sof(F1')=Sof(F2')=Sof(F3')=Sof(C8')=Sof(H8')=Sof(C9')=Sof(H9'A)=
 Sof(H9'B)=Sof(C10')=Sof(H10E)=Sof(H10F)=Sof(H11E)=Sof(H11F)=Sof(C12')=
 Sof(H12E)=Sof(H12F)=Sof(C13')=FVAR(1)
 Sof(S1A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9AA)=
 Sof(H9AB)=Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11C)=Sof(H11D)=
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=1-FVAR(2)
 Sof(S1)=Sof(F1)=Sof(F2)=Sof(F3)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9A)=Sof(H9B)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=
 Sof(H12B)=Sof(C13)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C8A(H8A), C8'(H8'), C8'A(H8'A)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB), C10(H10A,H10B), C10A(H10C,H10D), C11(H11A,H11B),
 C11A(H11C,H11D), C12(H12A,H12B), C12A(H12C,H12D), C9'(H9'A,H9'B), C9'A(H9'C,
 H9'D), C10'(H10E,H10F), C10B(H10G,H10H), C11'(H11E,H11F), C11'(H11G,H11H),
 C12'(H12E,H12F), C12B(H12G,H12H)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4')
;
_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 0.4703(4) 0.7016(3) 0.3879(2) 0.1071(8) Uani 0.832(7) 1 d . . P A 1
S1A S 0.456(3) 0.6710(13) 0.4237(10) 0.1071(8) Uani 0.168(7) 1 d D . P A 2
F1 F 0.0744(10) 0.6702(6) 0.3949(5) 0.134(2) Uani 0.832(7) 1 d D . P A 1
F1A F 0.085(5) 0.646(3) 0.447(3) 0.134(2) Uani 0.168(7) 1 d D . P A 2
F2 F 0.2733(12) 0.5448(5) 0.3855(5) 0.142(2) Uani 0.832(7) 1 d D . P A 1
F2A F 0.236(5) 0.578(2) 0.387(2) 0.142(2) Uani 0.168(7) 1 d D . P A 2
F3 F 0.2249(17) 0.5689(6) 0.5109(5) 0.169(3) Uani 0.832(7) 1 d D . P A 1
F3A F 0.240(6) 0.534(2) 0.507(2) 0.169(3) Uani 0.168(7) 1 d D . P A 2
N1 N 0.2446(7) 0.8894(4) 0.5604(3) 0.0869(12) Uani 1 1 d . . . . .
N2 N 0.5171(6) 0.8470(3) 0.6420(2) 0.0684(9) Uani 1 1 d D . . . .
C1 C 0.4282(10) 0.9563(4) 0.7353(4) 0.0863(14) Uani 1 1 d . . . . .
H1 H 0.5419 0.9387 0.7696 0.104 Uiso 1 1 calc R . . . .
C2 C 0.2790(11) 1.0227(4) 0.7468(4) 0.0954(17) Uani 1 1 d . . . . .
H2 H 0.2909 1.0505 0.7902 0.114 Uiso 1 1 calc R . . . .
C3 C 0.1089(10) 1.0502(4) 0.6951(4) 0.0894(15) Uani 1 1 d . . . . .
H3 H 0.0102 1.0958 0.7048 0.107 Uiso 1 1 calc R . . . .
C4 C 0.0839(8) 1.0113(4) 0.6302(3) 0.0805(12) Uani 1 1 d . . . . .
H4 H -0.0289 1.0304 0.5955 0.097 Uiso 1 1 calc R . . . .
C5 C 0.2341(7) 0.9422(3) 0.6185(3) 0.0697(10) Uani 1 1 d . . . . .
C6 C 0.4030(7) 0.9155(3) 0.6695(3) 0.0681(10) Uani 1 1 d . . . . .
C7 C 0.4106(8) 0.8327(4) 0.5784(3) 0.0787(12) Uani 1 1 d . . . . .
C8 C 0.4802(10) 0.7512(5) 0.5403(4) 0.0796(16) Uani 0.832(7) 1 d . . P A 1
H8 H 0.4092 0.6854 0.5763 0.096 Uiso 0.832(7) 1 calc R . P A 1
C8A C 0.539(4) 0.806(3) 0.504(2) 0.0796(16) Uani 0.168(7) 1 d D . P A 2
H8A H 0.6108 0.8620 0.4538 0.096 Uiso 0.168(7) 1 calc R . P A 2
C9 C 0.7132(11) 0.7299(7) 0.5497(5) 0.086(2) Uani 0.832(7) 1 d D . P A 1
H9A H 0.7531 0.6705 0.5337 0.103 Uiso 0.832(7) 1 calc R . P A 1
H9B H 0.7881 0.7910 0.5087 0.103 Uiso 0.832(7) 1 calc R . P A 1
C9A C 0.662(6) 0.714(3) 0.570(3) 0.086(2) Uani 0.168(7) 1 d D . P A 2
H9AA H 0.5704 0.6697 0.6184 0.103 Uiso 0.168(7) 1 calc R . P A 2
H9AB H 0.7243 0.6712 0.5387 0.103 Uiso 0.168(7) 1 calc R . P A 2
C10 C 0.7679(12) 0.7068(6) 0.6436(5) 0.094(2) Uani 0.832(7) 1 d D . P A 1
H10A H 0.9134 0.6909 0.6480 0.113 Uiso 0.832(7) 1 calc R . P A 1
H10B H 0.6942 0.6451 0.6844 0.113 Uiso 0.832(7) 1 calc R . P A 1
C10A C 0.828(6) 0.758(3) 0.607(3) 0.094(2) Uani 0.168(7) 1 d D . P A 2
H10C H 0.8916 0.8198 0.5611 0.113 Uiso 0.168(7) 1 calc R . P A 2
H10D H 0.9331 0.7052 0.6330 0.113 Uiso 0.168(7) 1 calc R . P A 2
C11 C 0.7162(19) 0.8001(14) 0.6724(8) 0.086(3) Uani 0.832(7) 1 d . . P A 1
H11A H 0.7137 0.7756 0.7372 0.103 Uiso 0.832(7) 1 calc R . P A 1
H11B H 0.8216 0.8530 0.6472 0.103 Uiso 0.832(7) 1 calc R . P A 1
C11A C 0.698(11) 0.785(9) 0.679(4) 0.086(3) Uani 0.168(7) 1 d D . P A 2
H11C H 0.6556 0.7204 0.7279 0.103 Uiso 0.168(7) 1 calc R . P A 2
H11D H 0.7800 0.8243 0.7022 0.103 Uiso 0.168(7) 1 calc R . P A 2
C12 C 0.4106(12) 0.7886(5) 0.4441(4) 0.0850(18) Uani 0.832(7) 1 d . . P A 1
H12A H 0.4731 0.8561 0.4089 0.102 Uiso 0.832(7) 1 calc R . P A 1
H12B H 0.2634 0.7999 0.4461 0.102 Uiso 0.832(7) 1 calc R . P A 1
C12A C 0.359(5) 0.748(2) 0.486(2) 0.0850(18) Uani 0.168(7) 1 d D . P A 2
H12C H 0.2591 0.7986 0.4525 0.102 Uiso 0.168(7) 1 calc R . P A 2
H12D H 0.2928 0.7021 0.5426 0.102 Uiso 0.168(7) 1 calc R . P A 2
C13 C 0.2412(14) 0.6148(6) 0.4233(5) 0.100(2) Uani 0.832(7) 1 d D . P A 1
C13A C 0.279(6) 0.625(2) 0.4394(19) 0.100(2) Uani 0.168(7) 1 d D . P A 2
S1' S 0.0748(6) 0.8111(2) 0.1409(3) 0.1434(13) Uani 0.824(4) 1 d D . P B 1
S1'A S 0.222(3) 0.7900(9) 0.1749(11) 0.1434(13) Uani 0.176(4) 1 d D . P B 2
F1' F 0.2947(16) 0.9130(7) -0.0018(5) 0.178(3) Uani 0.824(4) 1 d D . P B 1
F1'A F 0.069(5) 0.899(3) 0.0540(17) 0.178(3) Uani 0.176(4) 1 d D . P B 2
F2' F 0.4727(12) 0.8446(7) 0.1089(8) 0.181(3) Uani 0.824(4) 1 d D U P B 1
F2'A F 0.433(5) 0.886(3) 0.036(2) 0.181(3) Uani 0.176(4) 1 d D U P B 2
F3' F 0.271(2) 0.9793(6) 0.0937(7) 0.186(4) Uani 0.824(4) 1 d D U P B 1
F3'A F 0.287(9) 0.964(2) 0.130(3) 0.186(4) Uani 0.176(4) 1 d D U P B 2
N1' N 0.2384(6) 0.5043(3) 0.0964(3) 0.0779(10) Uani 1 1 d . . . . .
N2' N -0.0714(5) 0.4406(3) 0.1572(2) 0.0699(9) Uani 1 1 d . . . . .
C1' C -0.0363(9) 0.2658(4) 0.1393(4) 0.0846(13) Uani 1 1 d . . . . .
H1' H -0.1645 0.2392 0.1648 0.101 Uiso 1 1 calc R . . . .
C2' C 0.1013(11) 0.2092(4) 0.1079(4) 0.0966(17) Uani 1 1 d . . . . .
H2' H 0.0661 0.1425 0.1123 0.116 Uiso 1 1 calc R . . . .
C3' C 0.2917(10) 0.2483(4) 0.0698(4) 0.0903(15) Uani 1 1 d . . . . .
H3' H 0.3816 0.2070 0.0496 0.108 Uiso 1 1 calc R . . . .
C4' C 0.3520(8) 0.3461(4) 0.0608(3) 0.0783(12) Uani 1 1 d . . . . .
H4' H 0.4801 0.3718 0.0343 0.094 Uiso 1 1 calc R . . . .
C5' C 0.2154(7) 0.4061(3) 0.0926(3) 0.0653(10) Uani 1 1 d . . . . .
C6' C 0.0232(6) 0.3651(3) 0.1316(3) 0.0640(9) Uani 1 1 d . . . . .
C7' C 0.0639(7) 0.5206(4) 0.1354(3) 0.0739(11) Uani 1 1 d D . . . .
C8' C 0.0191(14) 0.6119(6) 0.1634(6) 0.099(2) Uani 0.824(4) 1 d D U P B 1
H8' H 0.0941 0.5866 0.2181 0.119 Uiso 0.824(4) 1 calc R . P B 1
C8'A C -0.033(6) 0.630(2) 0.124(3) 0.099(2) Uani 0.176(4) 1 d D U P B 2
H8'A H -0.0612 0.6704 0.0610 0.119 Uiso 0.176(4) 1 calc R . P B 2
C9' C -0.1875(15) 0.6121(9) 0.2046(8) 0.117(3) Uani 0.824(4) 1 d D U P B 1
H9'A H -0.2569 0.6745 0.1652 0.140 Uiso 0.824(4) 1 calc R . P B 1
H9'B H -0.1725 0.6222 0.2599 0.140 Uiso 0.824(4) 1 calc R . P B 1
C9'A C -0.229(8) 0.603(4) 0.183(3) 0.117(3) Uani 0.176(4) 1 d D U P B 2
H9'C H -0.3383 0.6112 0.1434 0.140 Uiso 0.176(4) 1 calc R . P B 2
H9'D H -0.2504 0.6582 0.2063 0.140 Uiso 0.176(4) 1 calc R . P B 2
C10' C -0.3288(14) 0.5239(7) 0.2267(8) 0.119(3) Uani 0.824(4) 1 d D U P B 1
H10E H -0.4548 0.5533 0.1985 0.143 Uiso 0.824(4) 1 calc R . P B 1
H10F H -0.3611 0.4977 0.2910 0.143 Uiso 0.824(4) 1 calc R . P B 1
C10B C -0.264(8) 0.498(3) 0.263(3) 0.119(3) Uani 0.176(4) 1 d D U P B 2
H10G H -0.3912 0.4970 0.2979 0.143 Uiso 0.176(4) 1 calc R . P B 2
H10H H -0.1503 0.4772 0.3012 0.143 Uiso 0.176(4) 1 calc R . P B 2
C11' C -0.2745(8) 0.4313(6) 0.2043(4) 0.0976(17) Uani 1 1 d D . . . .
H11E H -0.2770 0.3685 0.2590 0.117 Uiso 0.824(4) 1 calc R . P B 1
H11F H -0.3762 0.4234 0.1669 0.117 Uiso 0.824(4) 1 calc R . P B 1
H11G H -0.3041 0.3583 0.2416 0.117 Uiso 0.176(4) 1 calc R . P B 2
H11H H -0.3798 0.4588 0.1619 0.117 Uiso 0.176(4) 1 calc R . P B 2
C12' C 0.148(2) 0.7024(8) 0.1096(9) 0.131(4) Uani 0.824(4) 1 d D . P B 1
H12E H 0.1307 0.7214 0.0464 0.157 Uiso 0.824(4) 1 calc R . P B 1
H12F H 0.2912 0.6844 0.1202 0.157 Uiso 0.824(4) 1 calc R . P B 1
C12B C 0.152(9) 0.674(5) 0.150(5) 0.131(4) Uani 0.176(4) 1 d D . P B 2
H12G H 0.2564 0.6756 0.1042 0.157 Uiso 0.176(4) 1 calc R . P B 2
H12H H 0.1908 0.6158 0.2038 0.157 Uiso 0.176(4) 1 calc R . P B 2
C13' C 0.2864(19) 0.8843(8) 0.0893(8) 0.139(3) Uani 0.824(4) 1 d D . P B 1
C13B C 0.261(5) 0.908(2) 0.0785(18) 0.139(3) Uani 0.176(4) 1 d D . P B 2


_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 C12 1.779(6) . ?
S1 C13 1.868(11) . ?
S1A C12A 1.790(18) . ?
S1A C13A 1.30(4) . ?
F1 C13 1.313(9) . ?
F1A C13A 1.30(3) . ?
F2 C13 1.328(7) . ?
F2A C13A 1.30(2) . ?
F3 C13 1.310(9) . ?
F3A C13A 1.321(19) . ?
N1 C5 1.390(6) . ?
N1 C7 1.296(6) . ?
N2 C6 1.364(6) . ?
N2 C7 1.366(6) . ?
N2 C11 1.464(9) . ?
N2 C11A 1.45(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.362(8) . ?
C1 C6 1.405(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(7) . ?
C5 C6 1.383(6) . ?
C7 C8 1.515(7) . ?
C7 C8A 1.57(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.549(10) . ?
C8 C12 1.540(9) . ?
C8A H8A 0.9800 . ?
C8A C9A 1.55(2) . ?
C8A C12A 1.55(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.498(10) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.53(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.543(17) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A C11A 1.55(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
S1' C12' 1.792(10) . ?
S1' C13' 1.708(13) . ?
S1'A C12B 1.86(5) . ?
S1'A C13B 1.78(2) . ?
F1' C13' 1.370(11) . ?
F1'A C13B 1.366(15) . ?
F2' C13' 1.326(11) . ?
F2'A C13B 1.366(15) . ?
F3' C13' 1.336(9) . ?
F3'A C13B 1.363(15) . ?
N1' C5' 1.391(6) . ?
N1' C7' 1.317(6) . ?
N2' C6' 1.368(6) . ?
N2' C7' 1.361(6) . ?
N2' C11' 1.467(6) . ?
C1' H1' 0.9300 . ?
C1' C2' 1.362(9) . ?
C1' C6' 1.393(7) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.380(9) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.367(8) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.395(6) . ?
C5' C6' 1.401(6) . ?
C7' C8' 1.504(8) . ?
C7' C8'A 1.554(19) . ?
C8' H8' 0.9800 . ?
C8' C9' 1.463(10) . ?
C8' C12' 1.469(11) . ?
C8'A H8'A 0.9800 . ?
C8'A C9'A 1.51(2) . ?
C8'A C12B 1.54(2) . ?
C9' H9'A 0.9700 . ?
C9' H9'B 0.9700 . ?
C9' C10' 1.469(11) . ?
C9'A H9'C 0.9700 . ?
C9'A H9'D 0.9700 . ?
C9'A C10B 1.54(2) . ?
C10' H10E 0.9700 . ?
C10' H10F 0.9700 . ?
C10' C11' 1.478(10) . ?
C10B H10G 0.9700 . ?
C10B H10H 0.9700 . ?
C10B C11' 1.56(2) . ?
C11' H11E 0.9700 . ?
C11' H11F 0.9700 . ?
C11' H11G 0.9700 . ?
C11' H11H 0.9700 . ?
C12' H12E 0.9700 . ?
C12' H12F 0.9700 . ?
C12B H12G 0.9700 . ?
C12B H12H 0.9700 . ?

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
C12 S1 C13 101.3(3) . . ?
C13A S1A C12A 89.0(19) . . ?
C7 N1 C5 104.8(4) . . ?
C6 N2 C7 106.2(4) . . ?
C6 N2 C11 127.3(7) . . ?
C6 N2 C11A 130(3) . . ?
C7 N2 C11 126.5(7) . . ?
C7 N2 C11A 123(4) . . ?
C2 C1 H1 121.4 . . ?
C2 C1 C6 117.2(5) . . ?
C6 C1 H1 121.4 . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.7(5) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.5(5) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.4(5) . . ?
C5 C4 H4 121.3 . . ?
N1 C5 C4 129.5(4) . . ?
C6 C5 N1 109.5(4) . . ?
C6 C5 C4 121.0(4) . . ?
N2 C6 C1 132.7(4) . . ?
N2 C6 C5 106.1(4) . . ?
C5 C6 C1 121.2(5) . . ?
N1 C7 N2 113.4(4) . . ?
N1 C7 C8 125.8(5) . . ?
N1 C7 C8A 121.0(11) . . ?
N2 C7 C8 120.7(5) . . ?
N2 C7 C8A 116.9(11) . . ?
C7 C8 H8 107.7 . . ?
C7 C8 C9 109.8(6) . . ?
C7 C8 C12 108.1(5) . . ?
C9 C8 H8 107.7 . . ?
C12 C8 H8 107.7 . . ?
C12 C8 C9 115.5(6) . . ?
C7 C8A H8A 120.0 . . ?
C9A C8A C7 96(3) . . ?
C9A C8A H8A 120.0 . . ?
C9A C8A C12A 102(3) . . ?
C12A C8A C7 93.5(18) . . ?
C12A C8A H8A 120.0 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.2(6) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8A C9A H9AA 109.7 . . ?
C8A C9A H9AB 109.7 . . ?
H9AA C9A H9AB 108.2 . . ?
C10A C9A C8A 110(3) . . ?
C10A C9A H9AA 109.7 . . ?
C10A C9A H9AB 109.7 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C9 C10 C11 112.2(7) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9A C10A H10C 111.8 . . ?
C9A C10A H10D 111.8 . . ?
C9A C10A C11A 100(5) . . ?
H10C C10A H10D 109.5 . . ?
C11A C10A H10C 111.8 . . ?
C11A C10A H10D 111.8 . . ?
N2 C11 C10 110.8(11) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
N2 C11A C10A 111(3) . . ?
N2 C11A H11C 109.3 . . ?
N2 C11A H11D 109.3 . . ?
C10A C11A H11C 109.3 . . ?
C10A C11A H11D 109.3 . . ?
H11C C11A H11D 108.0 . . ?
S1 C12 H12A 108.4 . . ?
S1 C12 H12B 108.4 . . ?
C8 C12 S1 115.5(4) . . ?
C8 C12 H12A 108.4 . . ?
C8 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
S1A C12A H12C 109.8 . . ?
S1A C12A H12D 109.8 . . ?
C8A C12A S1A 110(2) . . ?
C8A C12A H12C 109.8 . . ?
C8A C12A H12D 109.8 . . ?
H12C C12A H12D 108.2 . . ?
F1 C13 S1 110.4(6) . . ?
F1 C13 F2 110.1(7) . . ?
F2 C13 S1 105.9(7) . . ?
F3 C13 S1 109.3(6) . . ?
F3 C13 F1 109.6(8) . . ?
F3 C13 F2 111.5(7) . . ?
S1A C13A F3A 123(3) . . ?
F1A C13A S1A 140(3) . . ?
F1A C13A F2A 89(3) . . ?
F1A C13A F3A 86(2) . . ?
F2A C13A S1A 117(2) . . ?
F2A C13A F3A 87(2) . . ?
C13' S1' C12' 95.2(4) . . ?
C13B S1'A C12B 114(3) . . ?
C7' N1' C5' 104.1(4) . . ?
C6' N2' C11' 125.4(4) . . ?
C7' N2' C6' 106.8(3) . . ?
C7' N2' C11' 127.7(5) . . ?
C2' C1' H1' 121.4 . . ?
C2' C1' C6' 117.2(5) . . ?
C6' C1' H1' 121.4 . . ?
C1' C2' H2' 119.2 . . ?
C1' C2' C3' 121.7(5) . . ?
C3' C2' H2' 119.2 . . ?
C2' C3' H3' 119.0 . . ?
C4' C3' C2' 121.9(5) . . ?
C4' C3' H3' 119.0 . . ?
C3' C4' H4' 121.0 . . ?
C3' C4' C5' 118.0(5) . . ?
C5' C4' H4' 121.0 . . ?
N1' C5' C4' 130.5(4) . . ?
N1' C5' C6' 110.0(4) . . ?
C4' C5' C6' 119.5(4) . . ?
N2' C6' C1' 132.8(4) . . ?
N2' C6' C5' 105.5(4) . . ?
C1' C6' C5' 121.7(5) . . ?
N1' C7' N2' 113.7(4) . . ?
N1' C7' C8' 124.9(5) . . ?
N1' C7' C8'A 126.0(14) . . ?
N2' C7' C8' 121.1(5) . . ?
N2' C7' C8'A 115.3(15) . . ?
C7' C8' H8' 98.4 . . ?
C9' C8' C7' 114.0(7) . . ?
C9' C8' H8' 98.4 . . ?
C9' C8' C12' 128.5(9) . . ?
C12' C8' C7' 111.1(6) . . ?
C12' C8' H8' 98.4 . . ?
C7' C8'A H8'A 111.0 . . ?
C9'A C8'A C7' 104(3) . . ?
C9'A C8'A H8'A 111.0 . . ?
C9'A C8'A C12B 121(5) . . ?
C12B C8'A C7' 97(3) . . ?
C12B C8'A H8'A 111.0 . . ?
C8' C9' H9'A 106.7 . . ?
C8' C9' H9'B 106.7 . . ?
C8' C9' C10' 122.6(8) . . ?
H9'A C9' H9'B 106.6 . . ?
C10' C9' H9'A 106.7 . . ?
C10' C9' H9'B 106.7 . . ?
C8'A C9'A H9'C 106.5 . . ?
C8'A C9'A H9'D 106.5 . . ?
C8'A C9'A C10B 123(4) . . ?
H9'C C9'A H9'D 106.5 . . ?
C10B C9'A H9'C 106.5 . . ?
C10B C9'A H9'D 106.5 . . ?
C9' C10' H10E 106.9 . . ?
C9' C10' H10F 106.9 . . ?
C9' C10' C11' 121.8(7) . . ?
H10E C10' H10F 106.7 . . ?
C11' C10' H10E 106.9 . . ?
C11' C10' H10F 106.9 . . ?
C9'A C10B H10G 112.7 . . ?
C9'A C10B H10H 112.7 . . ?
C9'A C10B C11' 95(3) . . ?
H10G C10B H10H 110.2 . . ?
C11' C10B H10G 112.7 . . ?
C11' C10B H10H 112.7 . . ?
N2' C11' C10' 112.3(6) . . ?
N2' C11' C10B 105.2(18) . . ?
N2' C11' H11E 109.1 . . ?
N2' C11' H11F 109.1 . . ?
N2' C11' H11G 110.7 . . ?
N2' C11' H11H 110.7 . . ?
C10' C11' H11E 109.1 . . ?
C10' C11' H11F 109.1 . . ?
C10B C11' H11G 110.7 . . ?
C10B C11' H11H 110.7 . . ?
H11E C11' H11F 107.9 . . ?
H11G C11' H11H 108.8 . . ?
S1' C12' H12E 109.9 . . ?
S1' C12' H12F 109.9 . . ?
C8' C12' S1' 108.8(7) . . ?
C8' C12' H12E 109.9 . . ?
C8' C12' H12F 109.9 . . ?
H12E C12' H12F 108.3 . . ?
S1'A C12B H12G 102.0 . . ?
S1'A C12B H12H 102.0 . . ?
C8'A C12B S1'A 140(4) . . ?
C8'A C12B H12G 102.0 . . ?
C8'A C12B H12H 102.0 . . ?
H12G C12B H12H 104.8 . . ?
F1' C13' S1' 111.8(9) . . ?
F2' C13' S1' 120.5(9) . . ?
F2' C13' F1' 102.0(10) . . ?
F2' C13' F3' 109.7(10) . . ?
F3' C13' S1' 110.7(9) . . ?
F3' C13' F1' 99.9(9) . . ?
F1'A C13B S1'A 89.8(14) . . ?
F1'A C13B F2'A 122(2) . . ?
F2'A C13B S1'A 102.9(17) . . ?
F3'A C13B S1'A 91.5(15) . . ?
F3'A C13B F1'A 120(2) . . ?
F3'A C13B F2'A 116(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.721
_oxdiff_exptl_absorpt_empirical_full_min 0.737
