# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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data_1471
_audit_block_doi                 10.5517/ccdc.csd.cc2cn2ns
_database_code_depnum_ccdc_archive 'CCDC 2194045'
loop_
_audit_author_name
_audit_author_address
lizhuoqin
;Xiangtan  University
China
;
_audit_update_record             
;
2022-08-01 deposited with the CCDC.	2024-07-04 downloaded from the CCDC.
;
_audit_creation_date             2022-07-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H15 F N2 O2 S'
_chemical_formula_sum            'C25 H15 F N2 O2 S'
_chemical_formula_weight         426.45
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.8743(5)
_cell_length_b                   20.4362(15)
_cell_length_c                   24.2525(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.218(4)
_cell_angle_gamma                90
_cell_volume                     3896.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4162
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      73.8030
_cell_measurement_theta_min      2.1570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light red'
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15433
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.681
_diffrn_reflns_theta_min         2.829
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  86.00   1.00    1.00    --   40.73  57.00 120.00   67
  2  ω     81.00 178.00   1.00    2.00    --  108.83  61.00 -60.00   97
  3  ω     69.00 128.00   1.00    2.00    --  108.83  15.00 -60.00   59
  4  ω     44.00 128.00   1.00    2.00    --  108.83 -30.00 -60.00   84
  5  ω     37.00 122.00   1.00    2.00    --  108.83-125.00 120.00   85
  6  ω     78.00 108.00   1.00    2.00    --  108.83 -95.00 120.00   30
  7  ω     35.00  99.00   1.00    2.00    --  108.83 -95.00 -90.00   64
  8  ω     28.00 102.00   1.00    2.00    --  108.83 -95.00-150.00   74
  9  ω    -65.00  34.00   1.00    1.00    --  -40.73  38.00 -90.00   99
 10  ω    -81.00 -11.00   1.00    1.00    --  -40.73 125.00 -60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0438940000
_diffrn_orient_matrix_UB_12      -0.0734665000
_diffrn_orient_matrix_UB_13      -0.0019120000
_diffrn_orient_matrix_UB_21      -0.0450974000
_diffrn_orient_matrix_UB_22      0.0027488000
_diffrn_orient_matrix_UB_23      0.0609127000
_diffrn_orient_matrix_UB_31      -0.1856840000
_diffrn_orient_matrix_UB_32      0.0166939000
_diffrn_orient_matrix_UB_33      -0.0181398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5412
_reflns_number_total             7670
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7670
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0865
_refine_ls_restrained_S_all      1.065
_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)+(0.0907P)²+9.2119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2183
_refine_ls_wR_factor_ref         0.2396
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C13(H13), C15(H15), C16(H16),
 C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C30(H30), C33(H33),
  C41(H41), C42(H42), C43(H43), C44(H44), C47(H47), C48(H48), C49(H49), C50(H50)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C34(H34A,H34B,H34C)
;
_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
S1 S 0.86384(15) 0.62947(6) 0.69116(4) 0.0389(3) Uani 1 1 d . . . . .
O1 O 0.8747(4) 0.76913(17) 0.52635(12) 0.0412(8) Uani 1 1 d . . . . .
O2 O 0.5456(4) 0.81975(18) 0.70822(12) 0.0427(8) Uani 1 1 d . . . . .
F1 F 1.0037(5) 0.93482(17) 0.81045(15) 0.0679(10) Uani 1 1 d . . . . .
N1 N 0.7645(5) 0.73280(19) 0.60567(13) 0.0320(8) Uani 1 1 d . . . . .
N2 N 0.7083(5) 0.7002(2) 0.85168(14) 0.0440(10) Uani 1 1 d . . . . .
C1 C 0.7917(5) 0.6153(2) 0.62232(16) 0.0342(9) Uani 1 1 d . . . . .
C2 C 0.7788(7) 0.5509(3) 0.6039(2) 0.0460(12) Uani 1 1 d . . . . .
H2 H 0.807410 0.516635 0.627867 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7230(7) 0.5379(3) 0.5495(2) 0.0494(12) Uani 1 1 d . . . . .
H3 H 0.719546 0.495089 0.536422 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6725(6) 0.5893(3) 0.51504(19) 0.0426(11) Uani 1 1 d . . . . .
H4 H 0.632710 0.580549 0.478959 0.051 Uiso 1 1 calc R U . . .
C5 C 0.6803(5) 0.6528(2) 0.53335(16) 0.0344(10) Uani 1 1 d . . . . .
H5 H 0.641620 0.686617 0.510277 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7470(5) 0.6666(2) 0.58702(16) 0.0329(9) Uani 1 1 d . . . . .
C7 C 0.7238(5) 0.7463(2) 0.66164(15) 0.0317(9) Uani 1 1 d . . . . .
C8 C 0.7674(5) 0.7050(2) 0.70364(16) 0.0319(9) Uani 1 1 d . . . . .
C9 C 0.7556(6) 0.7179(2) 0.76222(16) 0.0348(10) Uani 1 1 d . . . . .
C10 C 0.6986(6) 0.6743(3) 0.80028(17) 0.0421(11) Uani 1 1 d . . . . .
H10 H 0.658677 0.632429 0.791774 0.051 Uiso 1 1 calc R U . . .
C11 C 0.7759(6) 0.7625(3) 0.84853(17) 0.0445(12) Uani 1 1 d . . . . .
C12 C 0.8089(6) 0.7753(2) 0.79312(16) 0.0368(10) Uani 1 1 d . . . . .
C13 C 0.8850(6) 0.8347(3) 0.77958(19) 0.0424(11) Uani 1 1 d . . . . .
H13 H 0.906513 0.845252 0.743325 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9260(7) 0.8766(3) 0.8224(2) 0.0488(13) Uani 1 1 d . . . . .
C15 C 0.8935(8) 0.8651(3) 0.8774(2) 0.0587(16) Uani 1 1 d . . . . .
H15 H 0.920652 0.896324 0.904364 0.070 Uiso 1 1 calc R U . . .
C16 C 0.8203(7) 0.8065(3) 0.89103(19) 0.0543(15) Uani 1 1 d . . . . .
H16 H 0.800995 0.796474 0.927552 0.065 Uiso 1 1 calc R U . . .
C17 C 0.6460(7) 0.6699(4) 0.9009(2) 0.0618(17) Uani 1 1 d . . . . .
H17A H 0.735887 0.668452 0.929329 0.093 Uiso 1 1 calc R U . . .
H17B H 0.608243 0.626217 0.892367 0.093 Uiso 1 1 calc R U . . .
H17C H 0.552799 0.695026 0.913571 0.093 Uiso 1 1 calc R U . . .
C18 C 0.6433(5) 0.8108(2) 0.67155(15) 0.0341(10) Uani 1 1 d . . . . .
C19 C 0.6993(6) 0.8643(2) 0.63540(17) 0.0355(10) Uani 1 1 d . . . . .
C20 C 0.7829(6) 0.8497(2) 0.58816(17) 0.0348(10) Uani 1 1 d . . . . .
C21 C 0.8144(5) 0.7812(2) 0.57058(16) 0.0328(9) Uani 1 1 d . . . . .
C22 C 0.8329(6) 0.9007(2) 0.55427(18) 0.0393(10) Uani 1 1 d . . . . .
H22 H 0.887505 0.891467 0.522146 0.047 Uiso 1 1 calc R U . . .
C23 C 0.8012(7) 0.9647(3) 0.5685(2) 0.0495(13) Uani 1 1 d . . . . .
H23 H 0.834594 0.998525 0.545882 0.059 Uiso 1 1 calc R U . . .
C24 C 0.7195(7) 0.9789(3) 0.6165(2) 0.0492(12) Uani 1 1 d . . . . .
H24 H 0.699804 1.022191 0.626079 0.059 Uiso 1 1 calc R U . . .
C25 C 0.6677(6) 0.9291(3) 0.6498(2) 0.0445(11) Uani 1 1 d . . . . .
H25 H 0.612086 0.938524 0.681707 0.053 Uiso 1 1 calc R U . . .
S2 S 0.15675(15) 0.61845(6) 0.53079(4) 0.0399(3) Uani 1 1 d . . . . .
F2 F 0.0086(4) 0.90853(16) 0.39075(14) 0.0623(9) Uani 1 1 d . . . . .
O5 O 0.4674(4) 0.80910(18) 0.50414(12) 0.0437(8) Uani 1 1 d . . . . .
O6 O 0.1465(4) 0.76908(17) 0.68831(11) 0.0401(8) Uani 1 1 d . . . . .
N3 N 0.3257(5) 0.6749(2) 0.36698(15) 0.0446(10) Uani 1 1 d . . . . .
N4 N 0.2539(5) 0.72718(19) 0.60987(13) 0.0329(8) Uani 1 1 d . . . . .
C26 C 0.2563(6) 0.7369(3) 0.36567(17) 0.0403(11) Uani 1 1 d . . . . .
C27 C 0.2190(7) 0.7771(3) 0.32034(18) 0.0518(14) Uani 1 1 d . . . . .
H27 H 0.246026 0.764766 0.284987 0.062 Uiso 1 1 calc R U . . .
C28 C 0.1406(7) 0.8359(3) 0.3298(2) 0.0527(14) Uani 1 1 d . . . . .
H28 H 0.117464 0.865217 0.300992 0.063 Uiso 1 1 calc R U . . .
C29 C 0.0963(7) 0.8508(3) 0.3832(2) 0.0475(12) Uani 1 1 d . . . . .
C30 C 0.1329(6) 0.8135(2) 0.42865(18) 0.0393(10) Uani 1 1 d . . . . .
H30 H 0.104846 0.826602 0.463713 0.047 Uiso 1 1 calc R U . . .
C31 C 0.2158(5) 0.7538(2) 0.41951(16) 0.0337(10) Uani 1 1 d . . . . .
C32 C 0.2687(6) 0.7000(2) 0.45482(16) 0.0355(10) Uani 1 1 d . . . . .
C33 C 0.3320(6) 0.6535(3) 0.42029(17) 0.0412(11) Uani 1 1 d . . . . .
H33 H 0.373531 0.612847 0.431831 0.049 Uiso 1 1 calc R U . . .
C34 C 0.3881(7) 0.6399(3) 0.3199(2) 0.0581(16) Uani 1 1 d . . . . .
H34A H 0.301824 0.639654 0.290316 0.087 Uiso 1 1 calc R U . . .
H34B H 0.415405 0.595715 0.330488 0.087 Uiso 1 1 calc R U . . .
H34C H 0.488088 0.661262 0.307886 0.087 Uiso 1 1 calc R U . . .
C35 C 0.2529(5) 0.6924(2) 0.51425(17) 0.0334(9) Uani 1 1 d . . . . .
C36 C 0.2930(5) 0.7376(2) 0.55363(15) 0.0325(9) Uani 1 1 d . . . . .
C37 C 0.3683(6) 0.8018(2) 0.54038(16) 0.0355(10) Uani 1 1 d . . . . .
C38 C 0.3074(6) 0.8575(2) 0.57247(17) 0.0359(10) Uani 1 1 d . . . . .
C39 C 0.2263(5) 0.8455(2) 0.62133(17) 0.0345(10) Uani 1 1 d . . . . .
C40 C 0.2040(5) 0.7786(2) 0.64316(16) 0.0334(9) Uani 1 1 d . . . . .
C41 C 0.1740(6) 0.8988(3) 0.65256(19) 0.0417(11) Uani 1 1 d . . . . .
H41 H 0.123254 0.891717 0.685745 0.050 Uiso 1 1 calc R U . . .
C42 C 0.1977(7) 0.9616(3) 0.6342(2) 0.0486(12) Uani 1 1 d . . . . .
H42 H 0.164123 0.996729 0.655389 0.058 Uiso 1 1 calc R U . . .
C43 C 0.2712(7) 0.9732(3) 0.5844(2) 0.0512(13) Uani 1 1 d . . . . .
H43 H 0.281719 1.015796 0.571559 0.061 Uiso 1 1 calc R U . . .
C44 C 0.3285(7) 0.9215(3) 0.5540(2) 0.0449(12) Uani 1 1 d . . . . .
H44 H 0.381044 0.929215 0.521204 0.054 Uiso 1 1 calc R U . . .
C45 C 0.2788(6) 0.6630(2) 0.63241(17) 0.0358(10) Uani 1 1 d . . . . .
C46 C 0.2356(6) 0.6091(2) 0.59983(17) 0.0353(10) Uani 1 1 d . . . . .
C47 C 0.2567(7) 0.5460(3) 0.6207(2) 0.0495(12) Uani 1 1 d . . . . .
H47 H 0.229665 0.510045 0.598324 0.059 Uiso 1 1 calc R U . . .
C48 C 0.3184(7) 0.5368(3) 0.6751(2) 0.0512(13) Uani 1 1 d . . . . .
H48 H 0.328025 0.494931 0.689961 0.061 Uiso 1 1 calc R U . . .
C49 C 0.3656(7) 0.5913(3) 0.7069(2) 0.0480(12) Uani 1 1 d . . . . .
H49 H 0.408896 0.585388 0.743039 0.058 Uiso 1 1 calc R U . . .
C50 C 0.3493(6) 0.6540(3) 0.68583(17) 0.0389(10) Uani 1 1 d . . . . .
H50 H 0.385157 0.689831 0.707100 0.047 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
S1 C1 1.757(4) . ?
S1 C8 1.754(5) . ?
O1 C21 1.222(5) . ?
O2 C18 1.222(5) . ?
F1 C14 1.377(7) . ?
N1 C6 1.431(6) . ?
N1 C7 1.439(5) . ?
N1 C21 1.377(6) . ?
N2 C10 1.353(6) . ?
N2 C11 1.383(7) . ?
N2 C17 1.455(6) . ?
C1 C2 1.392(7) . ?
C1 C6 1.386(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.404(6) . ?
C7 C8 1.353(6) . ?
C7 C18 1.487(6) . ?
C8 C9 1.453(5) . ?
C9 C10 1.377(6) . ?
C9 C12 1.441(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.408(6) . ?
C11 C16 1.398(7) . ?
C12 C13 1.401(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(7) . ?
C14 C15 1.391(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(9) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.485(6) . ?
C19 C20 1.385(6) . ?
C19 C25 1.395(7) . ?
C20 C21 1.489(6) . ?
C20 C22 1.397(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.378(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.393(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.375(7) . ?
C25 H25 0.9300 . ?
S2 C35 1.747(5) . ?
S2 C46 1.763(4) . ?
F2 C29 1.384(7) . ?
O5 C37 1.217(5) . ?
O6 C40 1.224(5) . ?
N3 C26 1.380(7) . ?
N3 C33 1.363(6) . ?
N3 C34 1.456(6) . ?
N4 C36 1.431(5) . ?
N4 C40 1.395(6) . ?
N4 C45 1.430(6) . ?
C26 C27 1.391(7) . ?
C26 C31 1.404(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.375(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.395(8) . ?
C29 C30 1.358(7) . ?
C30 H30 0.9300 . ?
C30 C31 1.408(7) . ?
C31 C32 1.441(6) . ?
C32 C33 1.378(6) . ?
C32 C35 1.462(5) . ?
C33 H33 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.354(6) . ?
C36 C37 1.482(7) . ?
C37 C38 1.474(6) . ?
C38 C39 1.399(6) . ?
C38 C44 1.395(7) . ?
C39 C40 1.481(7) . ?
C39 C41 1.402(6) . ?
C41 H41 0.9300 . ?
C41 C42 1.374(7) . ?
C42 H42 0.9300 . ?
C42 C43 1.389(8) . ?
C43 H43 0.9300 . ?
C43 C44 1.379(8) . ?
C44 H44 0.9300 . ?
C45 C46 1.386(6) . ?
C45 C50 1.393(6) . ?
C46 C47 1.393(7) . ?
C47 H47 0.9300 . ?
C47 C48 1.394(7) . ?
C48 H48 0.9300 . ?
C48 C49 1.393(8) . ?
C49 H49 0.9300 . ?
C49 C50 1.383(7) . ?
C50 H50 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
C8 S1 C1 100.9(2) . . ?
C6 N1 C7 117.2(4) . . ?
C21 N1 C6 120.7(3) . . ?
C21 N1 C7 122.1(4) . . ?
C10 N2 C11 108.2(4) . . ?
C10 N2 C17 125.8(5) . . ?
C11 N2 C17 125.9(5) . . ?
C2 C1 S1 118.3(4) . . ?
C6 C1 S1 121.3(4) . . ?
C6 C1 C2 120.3(4) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.9(5) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 N1 120.2(4) . . ?
C1 C6 C5 119.3(4) . . ?
C5 C6 N1 120.5(4) . . ?
N1 C7 C18 116.2(4) . . ?
C8 C7 N1 122.0(4) . . ?
C8 C7 C18 121.6(4) . . ?
C7 C8 S1 120.9(3) . . ?
C7 C8 C9 126.5(4) . . ?
C9 C8 S1 112.4(3) . . ?
C10 C9 C8 125.3(5) . . ?
C10 C9 C12 106.0(4) . . ?
C12 C9 C8 128.6(4) . . ?
N2 C10 C9 111.1(5) . . ?
N2 C10 H10 124.5 . . ?
C9 C10 H10 124.5 . . ?
N2 C11 C12 108.5(4) . . ?
N2 C11 C16 129.2(5) . . ?
C16 C11 C12 122.1(6) . . ?
C11 C12 C9 106.3(4) . . ?
C13 C12 C9 134.4(4) . . ?
C13 C12 C11 119.3(4) . . ?
C12 C13 H13 121.7 . . ?
C14 C13 C12 116.6(5) . . ?
C14 C13 H13 121.7 . . ?
F1 C14 C15 117.1(5) . . ?
C13 C14 F1 117.9(5) . . ?
C13 C14 C15 125.0(6) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.6(5) . . ?
C16 C15 H15 120.7 . . ?
C11 C16 H16 120.9 . . ?
C15 C16 C11 118.3(5) . . ?
C15 C16 H16 120.9 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 C7 122.8(4) . . ?
O2 C18 C19 122.7(4) . . ?
C19 C18 C7 114.4(4) . . ?
C20 C19 C18 120.0(4) . . ?
C20 C19 C25 120.8(5) . . ?
C25 C19 C18 119.2(4) . . ?
C19 C20 C21 122.3(4) . . ?
C19 C20 C22 119.3(5) . . ?
C22 C20 C21 118.4(4) . . ?
O1 C21 N1 122.4(4) . . ?
O1 C21 C20 121.4(4) . . ?
N1 C21 C20 116.2(4) . . ?
C20 C22 H22 120.0 . . ?
C23 C22 C20 119.9(5) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.4(5) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.2(5) . . ?
C25 C24 H24 119.9 . . ?
C19 C25 H25 120.3 . . ?
C24 C25 C19 119.5(5) . . ?
C24 C25 H25 120.3 . . ?
C35 S2 C46 100.2(2) . . ?
C26 N3 C34 125.7(4) . . ?
C33 N3 C26 108.1(4) . . ?
C33 N3 C34 126.1(5) . . ?
C40 N4 C36 121.5(4) . . ?
C40 N4 C45 120.4(3) . . ?
C45 N4 C36 118.0(4) . . ?
N3 C26 C27 128.8(5) . . ?
N3 C26 C31 108.3(4) . . ?
C27 C26 C31 122.8(5) . . ?
C26 C27 H27 121.3 . . ?
C28 C27 C26 117.5(5) . . ?
C28 C27 H27 121.3 . . ?
C27 C28 H28 120.5 . . ?
C27 C28 C29 118.9(5) . . ?
C29 C28 H28 120.5 . . ?
F2 C29 C28 117.5(5) . . ?
C30 C29 F2 117.1(5) . . ?
C30 C29 C28 125.4(6) . . ?
C29 C30 H30 122.0 . . ?
C29 C30 C31 116.0(5) . . ?
C31 C30 H30 122.0 . . ?
C26 C31 C30 119.4(4) . . ?
C26 C31 C32 107.0(4) . . ?
C30 C31 C32 133.6(4) . . ?
C31 C32 C35 129.0(4) . . ?
C33 C32 C31 105.5(4) . . ?
C33 C32 C35 125.4(4) . . ?
N3 C33 C32 111.1(5) . . ?
N3 C33 H33 124.5 . . ?
C32 C33 H33 124.5 . . ?
N3 C34 H34A 109.5 . . ?
N3 C34 H34B 109.5 . . ?
N3 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C35 S2 112.4(3) . . ?
C36 C35 S2 121.0(3) . . ?
C36 C35 C32 126.4(4) . . ?
N4 C36 C37 116.7(4) . . ?
C35 C36 N4 121.1(4) . . ?
C35 C36 C37 122.1(4) . . ?
O5 C37 C36 123.1(4) . . ?
O5 C37 C38 121.8(4) . . ?
C38 C37 C36 115.1(4) . . ?
C39 C38 C37 119.3(4) . . ?
C44 C38 C37 120.4(4) . . ?
C44 C38 C39 120.3(5) . . ?
C38 C39 C40 122.3(4) . . ?
C38 C39 C41 118.9(5) . . ?
C41 C39 C40 118.7(4) . . ?
O6 C40 N4 121.9(4) . . ?
O6 C40 C39 121.6(4) . . ?
N4 C40 C39 116.5(4) . . ?
C39 C41 H41 120.0 . . ?
C42 C41 C39 120.1(5) . . ?
C42 C41 H41 120.0 . . ?
C41 C42 H42 119.6 . . ?
C41 C42 C43 120.8(5) . . ?
C43 C42 H42 119.6 . . ?
C42 C43 H43 120.0 . . ?
C44 C43 C42 119.9(5) . . ?
C44 C43 H43 120.0 . . ?
C38 C44 H44 120.1 . . ?
C43 C44 C38 119.8(5) . . ?
C43 C44 H44 120.1 . . ?
C46 C45 N4 119.1(4) . . ?
C46 C45 C50 119.9(4) . . ?
C50 C45 N4 121.0(4) . . ?
C45 C46 S2 121.2(4) . . ?
C45 C46 C47 120.6(4) . . ?
C47 C46 S2 118.2(4) . . ?
C46 C47 H47 120.1 . . ?
C48 C47 C46 119.8(5) . . ?
C48 C47 H47 120.1 . . ?
C47 C48 H48 120.5 . . ?
C49 C48 C47 119.0(5) . . ?
C49 C48 H48 120.5 . . ?
C48 C49 H49 119.3 . . ?
C50 C49 C48 121.3(5) . . ?
C50 C49 H49 119.3 . . ?
C45 C50 H50 120.3 . . ?
C49 C50 C45 119.3(5) . . ?
C49 C50 H50 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 -179.7(4) . . . . ?
S1 C1 C6 N1 2.2(6) . . . . ?
S1 C1 C6 C5 -176.2(3) . . . . ?
S1 C8 C9 C10 -47.0(6) . . . . ?
S1 C8 C9 C12 128.7(4) . . . . ?
O2 C18 C19 C20 -167.6(4) . . . . ?
O2 C18 C19 C25 12.8(6) . . . . ?
F1 C14 C15 C16 -178.2(5) . . . . ?
N1 C7 C8 S1 -4.4(6) . . . . ?
N1 C7 C8 C9 170.3(4) . . . . ?
N1 C7 C18 O2 150.9(4) . . . . ?
N1 C7 C18 C19 -32.6(5) . . . . ?
N2 C11 C12 C9 0.8(5) . . . . ?
N2 C11 C12 C13 -177.4(4) . . . . ?
N2 C11 C16 C15 177.0(5) . . . . ?
C1 S1 C8 C7 -24.9(4) . . . . ?
C1 S1 C8 C9 159.8(3) . . . . ?
C1 C2 C3 C4 -3.3(8) . . . . ?
C2 C1 C6 N1 -178.4(4) . . . . ?
C2 C1 C6 C5 3.2(7) . . . . ?
C2 C3 C4 C5 1.5(8) . . . . ?
C3 C4 C5 C6 2.7(7) . . . . ?
C4 C5 C6 N1 176.6(4) . . . . ?
C4 C5 C6 C1 -5.0(7) . . . . ?
C6 N1 C7 C8 39.8(6) . . . . ?
C6 N1 C7 C18 -144.8(4) . . . . ?
C6 N1 C21 O1 -13.5(6) . . . . ?
C6 N1 C21 C20 163.5(4) . . . . ?
C6 C1 C2 C3 0.9(7) . . . . ?
C7 N1 C6 C1 -38.1(6) . . . . ?
C7 N1 C6 C5 140.3(4) . . . . ?
C7 N1 C21 O1 168.1(4) . . . . ?
C7 N1 C21 C20 -14.9(6) . . . . ?
C7 C8 C9 C10 138.0(5) . . . . ?
C7 C8 C9 C12 -46.3(7) . . . . ?
C7 C18 C19 C20 15.9(5) . . . . ?
C7 C18 C19 C25 -163.7(4) . . . . ?
C8 S1 C1 C2 -153.4(4) . . . . ?
C8 S1 C1 C6 25.9(4) . . . . ?
C8 C7 C18 O2 -33.7(7) . . . . ?
C8 C7 C18 C19 142.7(4) . . . . ?
C8 C9 C10 N2 177.9(4) . . . . ?
C8 C9 C12 C11 -177.7(4) . . . . ?
C8 C9 C12 C13 0.1(9) . . . . ?
C9 C12 C13 C14 -176.2(5) . . . . ?
C10 N2 C11 C12 0.1(5) . . . . ?
C10 N2 C11 C16 -175.3(5) . . . . ?
C10 C9 C12 C11 -1.4(5) . . . . ?
C10 C9 C12 C13 176.4(5) . . . . ?
C11 N2 C10 C9 -1.0(6) . . . . ?
C11 C12 C13 C14 1.3(7) . . . . ?
C12 C9 C10 N2 1.5(5) . . . . ?
C12 C11 C16 C15 2.2(7) . . . . ?
C12 C13 C14 F1 178.9(4) . . . . ?
C12 C13 C14 C15 -1.9(8) . . . . ?
C13 C14 C15 C16 2.6(8) . . . . ?
C14 C15 C16 C11 -2.6(8) . . . . ?
C16 C11 C12 C9 176.6(4) . . . . ?
C16 C11 C12 C13 -1.6(7) . . . . ?
C17 N2 C10 C9 174.6(4) . . . . ?
C17 N2 C11 C12 -175.5(4) . . . . ?
C17 N2 C11 C16 9.1(8) . . . . ?
C18 C7 C8 S1 -179.5(3) . . . . ?
C18 C7 C8 C9 -4.9(7) . . . . ?
C18 C19 C20 C21 2.2(6) . . . . ?
C18 C19 C20 C22 179.2(4) . . . . ?
C18 C19 C25 C24 179.9(4) . . . . ?
C19 C20 C21 O1 173.4(4) . . . . ?
C19 C20 C21 N1 -3.6(6) . . . . ?
C19 C20 C22 C23 1.0(6) . . . . ?
C20 C19 C25 C24 0.4(7) . . . . ?
C20 C22 C23 C24 0.0(7) . . . . ?
C21 N1 C6 C1 143.4(4) . . . . ?
C21 N1 C6 C5 -38.2(6) . . . . ?
C21 N1 C7 C8 -141.7(4) . . . . ?
C21 N1 C7 C18 33.7(6) . . . . ?
C21 C20 C22 C23 178.1(4) . . . . ?
C22 C20 C21 O1 -3.6(6) . . . . ?
C22 C20 C21 N1 179.3(4) . . . . ?
C22 C23 C24 C25 -0.8(8) . . . . ?
C23 C24 C25 C19 0.6(7) . . . . ?
C25 C19 C20 C21 -178.2(4) . . . . ?
C25 C19 C20 C22 -1.2(6) . . . . ?
S2 C35 C36 N4 -1.7(6) . . . . ?
S2 C35 C36 C37 -177.5(3) . . . . ?
S2 C46 C47 C48 -179.9(4) . . . . ?
F2 C29 C30 C31 177.4(4) . . . . ?
O5 C37 C38 C39 -165.4(4) . . . . ?
O5 C37 C38 C44 15.5(6) . . . . ?
N3 C26 C27 C28 176.3(5) . . . . ?
N3 C26 C31 C30 -176.0(4) . . . . ?
N3 C26 C31 C32 1.9(5) . . . . ?
N4 C36 C37 O5 149.1(4) . . . . ?
N4 C36 C37 C38 -33.9(5) . . . . ?
N4 C45 C46 S2 1.9(6) . . . . ?
N4 C45 C46 C47 -179.4(4) . . . . ?
N4 C45 C50 C49 177.6(4) . . . . ?
C26 N3 C33 C32 -0.2(6) . . . . ?
C26 C27 C28 C29 -2.7(7) . . . . ?
C26 C31 C32 C33 -1.9(5) . . . . ?
C26 C31 C32 C35 -178.9(4) . . . . ?
C27 C26 C31 C30 0.4(7) . . . . ?
C27 C26 C31 C32 178.3(4) . . . . ?
C27 C28 C29 F2 -176.3(4) . . . . ?
C27 C28 C29 C30 4.1(8) . . . . ?
C28 C29 C30 C31 -2.9(8) . . . . ?
C29 C30 C31 C26 0.6(6) . . . . ?
C29 C30 C31 C32 -176.6(5) . . . . ?
C30 C31 C32 C33 175.5(5) . . . . ?
C30 C31 C32 C35 -1.4(8) . . . . ?
C31 C26 C27 C28 0.7(7) . . . . ?
C31 C32 C33 N3 1.3(5) . . . . ?
C31 C32 C35 S2 128.0(4) . . . . ?
C31 C32 C35 C36 -46.9(7) . . . . ?
C32 C35 C36 N4 172.8(4) . . . . ?
C32 C35 C36 C37 -3.0(7) . . . . ?
C33 N3 C26 C27 -177.3(5) . . . . ?
C33 N3 C26 C31 -1.1(5) . . . . ?
C33 C32 C35 S2 -48.4(6) . . . . ?
C33 C32 C35 C36 136.7(5) . . . . ?
C34 N3 C26 C27 5.2(8) . . . . ?
C34 N3 C26 C31 -178.6(4) . . . . ?
C34 N3 C33 C32 177.3(4) . . . . ?
C35 S2 C46 C45 28.0(4) . . . . ?
C35 S2 C46 C47 -150.8(4) . . . . ?
C35 C32 C33 N3 178.4(4) . . . . ?
C35 C36 C37 O5 -34.9(7) . . . . ?
C35 C36 C37 C38 142.0(4) . . . . ?
C36 N4 C40 O6 169.1(4) . . . . ?
C36 N4 C40 C39 -11.7(6) . . . . ?
C36 N4 C45 C46 -39.7(6) . . . . ?
C36 N4 C45 C50 138.7(4) . . . . ?
C36 C37 C38 C39 17.6(5) . . . . ?
C36 C37 C38 C44 -161.5(4) . . . . ?
C37 C38 C39 C40 2.0(6) . . . . ?
C37 C38 C39 C41 177.9(4) . . . . ?
C37 C38 C44 C43 -179.9(4) . . . . ?
C38 C39 C40 O6 173.4(4) . . . . ?
C38 C39 C40 N4 -5.8(6) . . . . ?
C38 C39 C41 C42 2.1(7) . . . . ?
C39 C38 C44 C43 0.9(7) . . . . ?
C39 C41 C42 C43 0.9(7) . . . . ?
C40 N4 C36 C35 -144.0(4) . . . . ?
C40 N4 C36 C37 32.0(6) . . . . ?
C40 N4 C45 C46 144.5(4) . . . . ?
C40 N4 C45 C50 -37.1(6) . . . . ?
C40 C39 C41 C42 178.1(4) . . . . ?
C41 C39 C40 O6 -2.4(6) . . . . ?
C41 C39 C40 N4 178.4(4) . . . . ?
C41 C42 C43 C44 -3.0(8) . . . . ?
C42 C43 C44 C38 2.1(8) . . . . ?
C44 C38 C39 C40 -178.8(4) . . . . ?
C44 C38 C39 C41 -3.0(6) . . . . ?
C45 N4 C36 C35 40.3(6) . . . . ?
C45 N4 C36 C37 -143.7(4) . . . . ?
C45 N4 C40 O6 -15.3(6) . . . . ?
C45 N4 C40 C39 163.9(4) . . . . ?
C45 C46 C47 C48 1.3(8) . . . . ?
C46 S2 C35 C32 156.6(3) . . . . ?
C46 S2 C35 C36 -28.2(4) . . . . ?
C46 C45 C50 C49 -4.0(7) . . . . ?
C46 C47 C48 C49 -3.0(8) . . . . ?
C47 C48 C49 C50 1.2(8) . . . . ?
C48 C49 C50 C45 2.3(8) . . . . ?
C50 C45 C46 S2 -176.5(3) . . . . ?
C50 C45 C46 C47 2.2(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.205
_oxdiff_exptl_absorpt_empirical_full_min 0.605
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
