# Electronic Supplementary Material (ESI) for ChemComm.
# 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_exp_3908
_database_code_depnum_ccdc_archive 'CCDC 2076659'
loop_
_audit_author_name
_audit_author_address
'Feng Wanzhong k'
;shandong normal university
China
;
_audit_update_record             
;
2021-04-11 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2020-10-09
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C18 H13 Cl F N O2 S)'
_chemical_formula_sum            'C36 H26 Cl2 F2 N2 O4 S2'
_chemical_formula_weight         723.61
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     CHNOCl
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.5995(5)
_cell_length_b                   11.0868(7)
_cell_length_c                   18.5904(14)
_cell_angle_alpha                96.689(6)
_cell_angle_beta                 101.847(6)
_cell_angle_gamma                99.853(5)
_cell_volume                     1687.83(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3031
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6730
_cell_measurement_theta_min      6.3290
_exptl_absorpt_coefficient_mu    3.345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11108
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.07
_diffrn_reflns_theta_min         4.10
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9776
_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  67.00   1.00    1.00    --    0.00  57.00-120.00   48
  2  ω     33.00  69.00   1.00    1.00    --    0.00  57.00 -60.00   36
  3  ω    -63.00 -27.00   1.00    1.00    --    0.00 -57.00 150.00   36
  4  ω    -16.00  21.00   1.00    1.00    --    0.00 -57.00 150.00   37
  5  ω     26.00 104.00   1.00    1.45    --   54.00-125.00-120.00   78
  6  ω    -18.00  75.00   1.00    1.45    --   54.00 -37.00  60.00   93
  7  ω     36.00  86.00   1.00    1.45    --   54.00-125.00  90.00   50
  8  ω     77.00 123.00   1.00    1.45    --   54.00  37.00-120.00   46
  9  ω     15.00  80.00   1.00    1.45    --   54.00 -37.00-150.00   65
 10  ω     29.00  57.00   1.00    1.45    --   54.00  37.00-120.00   28
 11  ω     30.00 126.00   1.00    1.45    --   54.00  37.00  30.00   96
 12  ω     79.00 106.00   1.00    1.45    --  108.00-111.00  90.00   27
 13  ω     65.00 112.00   1.00    1.45    --  108.00-111.00-180.00   47
 14  ω     93.00 171.00   1.00    1.45    --  108.00  77.00-120.00   78
 15  ω     63.00 129.00   1.00    1.45    --  108.00 -63.00 -90.00   66
 16  ω    102.00 178.00   1.00    1.45    --  108.00  37.00 -60.00   76
 17  ω     38.00  69.00   1.00    1.45    --  108.00 -77.00  30.00   31
 18  ω    131.00 175.00   1.00    1.45    --  108.00  63.00 -30.00   44
 19  ω     86.00 128.00   1.00    1.45    --  108.00  63.00 -30.00   42
 20  ω     44.00 142.00   1.00    1.45    --  108.00 -91.00-150.00   98
 21  ω    112.00 137.00   1.00    1.45    --  108.00 178.00 150.00   25
 22  ω     41.00  97.00   1.00    1.45    --  108.00 -50.00  90.00   56
 23  ω     85.00 111.00   1.00    1.45    --  108.00-111.00   0.00   26
 24  ω     66.00 102.00   1.00    1.45    --  108.00 178.00 150.00   36
 25  ω     83.00 120.00   1.00    1.45    --  108.00 178.00-180.00   37
 26  ω     91.00 116.00   1.00    1.45    --  108.00  63.00 120.00   25
 27  ω     38.00 128.00   1.00    1.45    --  108.00 -50.00-180.00   90
 28  ω     87.00 112.00   1.00    1.45    --  108.00 -77.00  30.00   25
 29  ω     87.00 166.00   1.00    1.45    --  108.00  37.00  30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0842983000
_diffrn_orient_matrix_UB_12      0.1311661000
_diffrn_orient_matrix_UB_13      -0.0066448000
_diffrn_orient_matrix_UB_21      -0.1040623000
_diffrn_orient_matrix_UB_22      -0.0137782000
_diffrn_orient_matrix_UB_23      -0.0796534000
_diffrn_orient_matrix_UB_31      -0.1302891000
_diffrn_orient_matrix_UB_32      0.0547775000
_diffrn_orient_matrix_UB_33      0.0310201000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4322
_reflns_number_total             6014
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6014
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0708P)²+0.1033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1447
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C11(H11), C14(H14), C15(H15),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27), C30(H30),
  C33(H33), C34(H34), C36(H36), C37(H37)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6061(4) 0.1348(4) 0.89038(17) 0.0773(9) Uani 1 1 d . . .
C2 C 0.7393(5) 0.0931(5) 0.9271(2) 0.0975(13) Uani 1 1 d . . .
H2 H 0.8423 0.1431 0.9385 0.117 Uiso 1 1 calc R . .
C3 C 0.7156(5) -0.0249(5) 0.9465(2) 0.1030(14) Uani 1 1 d . . .
H3 H 0.8034 -0.0532 0.9722 0.124 Uiso 1 1 calc R . .
C4 C 0.5675(5) -0.0988(4) 0.9285(2) 0.0945(12) Uani 1 1 d . . .
H4 H 0.5538 -0.1783 0.9407 0.113 Uiso 1 1 calc R . .
C5 C 0.4355(4) -0.0562(3) 0.89185(18) 0.0742(9) Uani 1 1 d . . .
H5 H 0.3338 -0.1083 0.8793 0.089 Uiso 1 1 calc R . .
C6 C 0.4510(3) 0.0618(3) 0.87341(16) 0.0615(7) Uani 1 1 d . . .
C7 C 0.3070(3) 0.1045(3) 0.83364(15) 0.0552(7) Uani 1 1 d . . .
C8 C 0.2175(3) 0.0401(3) 0.76491(15) 0.0579(7) Uani 1 1 d . . .
H8 H 0.2508 -0.0297 0.7455 0.070 Uiso 1 1 calc R . .
C10 C 0.0423(3) 0.1711(2) 0.75396(15) 0.0497(6) Uani 1 1 d . . .
C11 C 0.1185(4) 0.2425(3) 0.82175(16) 0.0622(7) Uani 1 1 d . . .
H11 H 0.0830 0.3121 0.8399 0.075 Uiso 1 1 calc R . .
C12 C 0.2495(4) 0.2047(3) 0.86067(15) 0.0624(7) Uani 1 1 d . . .
C13 C -0.0693(3) 0.2359(2) 0.61496(16) 0.0502(6) Uani 1 1 d . . .
C14 C -0.0994(3) 0.1392(3) 0.55683(17) 0.0625(7) Uani 1 1 d . . .
H14 H -0.1535 0.0610 0.5609 0.075 Uiso 1 1 calc R . .
C15 C -0.0488(4) 0.1592(3) 0.49282(18) 0.0677(8) Uani 1 1 d . . .
H15 H -0.0701 0.0943 0.4534 0.081 Uiso 1 1 calc R . .
C16 C 0.0334(3) 0.2748(3) 0.48631(18) 0.0656(8) Uani 1 1 d . . .
C17 C 0.0624(4) 0.3696(3) 0.5446(2) 0.0693(9) Uani 1 1 d . . .
H17 H 0.1169 0.4476 0.5405 0.083 Uiso 1 1 calc R . .
C18 C 0.0128(3) 0.3522(3) 0.60945(18) 0.0609(7) Uani 1 1 d . . .
H18 H 0.0340 0.4174 0.6487 0.073 Uiso 1 1 calc R . .
C19 C 0.0904(4) 0.2951(4) 0.4160(2) 0.0935(13) Uani 1 1 d . . .
H19A H 0.0461 0.3609 0.3956 0.140 Uiso 1 1 calc R . .
H19B H 0.0547 0.2204 0.3804 0.140 Uiso 1 1 calc R . .
H19C H 0.2067 0.3170 0.4276 0.140 Uiso 1 1 calc R . .
C20 C -0.0407(4) 0.3625(3) 0.09838(17) 0.0701(8) Uani 1 1 d . . .
C21 C -0.1773(5) 0.4005(4) 0.0619(2) 0.0938(12) Uani 1 1 d . . .
H21 H -0.1892 0.4125 0.0126 0.113 Uiso 1 1 calc R . .
C22 C -0.2954(5) 0.4202(4) 0.0998(3) 0.0937(12) Uani 1 1 d . . .
H22 H -0.3880 0.4447 0.0756 0.112 Uiso 1 1 calc R . .
C23 C -0.2771(4) 0.4039(3) 0.1726(2) 0.0865(10) Uani 1 1 d . . .
H23 H -0.3565 0.4179 0.1980 0.104 Uiso 1 1 calc R . .
C24 C -0.1417(4) 0.3672(3) 0.20773(18) 0.0686(8) Uani 1 1 d . . .
H24 H -0.1306 0.3562 0.2572 0.082 Uiso 1 1 calc R . .
C25 C -0.0204(3) 0.3457(3) 0.17222(15) 0.0543(6) Uani 1 1 d . . .
C26 C 0.1284(3) 0.3115(2) 0.21386(14) 0.0497(6) Uani 1 1 d . . .
C27 C 0.2470(4) 0.4000(3) 0.26328(16) 0.0618(7) Uani 1 1 d . . .
H27 H 0.2316 0.4813 0.2681 0.074 Uiso 1 1 calc R . .
C29 C 0.4007(3) 0.2612(2) 0.29708(14) 0.0480(6) Uani 1 1 d . . .
C30 C 0.2929(3) 0.1630(2) 0.25033(15) 0.0543(6) Uani 1 1 d . . .
H30 H 0.3106 0.0823 0.2473 0.065 Uiso 1 1 calc R . .
C31 C 0.1574(3) 0.1927(2) 0.20862(15) 0.0523(6) Uani 1 1 d . . .
C32 C 0.5355(3) 0.2448(2) 0.44400(14) 0.0453(6) Uani 1 1 d . . .
C33 C 0.4519(3) 0.1397(3) 0.46340(16) 0.0562(7) Uani 1 1 d . . .
H33 H 0.4214 0.0653 0.4306 0.067 Uiso 1 1 calc R . .
C34 C 0.4148(3) 0.1476(3) 0.53263(17) 0.0608(7) Uani 1 1 d . . .
H34 H 0.3604 0.0771 0.5463 0.073 Uiso 1 1 calc R . .
C35 C 0.4565(3) 0.2573(3) 0.58186(15) 0.0531(7) Uani 1 1 d . . .
C36 C 0.5384(3) 0.3601(3) 0.56121(16) 0.0609(7) Uani 1 1 d . . .
H36 H 0.5677 0.4346 0.5939 0.073 Uiso 1 1 calc R . .
C37 C 0.5782(3) 0.3549(3) 0.49242(16) 0.0567(7) Uani 1 1 d . . .
H37 H 0.6334 0.4255 0.4791 0.068 Uiso 1 1 calc R . .
C38 C 0.4150(4) 0.2629(4) 0.65724(17) 0.0778(10) Uani 1 1 d . . .
H38A H 0.4906 0.2281 0.6901 0.117 Uiso 1 1 calc R . .
H38B H 0.3072 0.2165 0.6520 0.117 Uiso 1 1 calc R . .
H38C H 0.4209 0.3477 0.6776 0.117 Uiso 1 1 calc R . .
Cl1 Cl 0.63686(13) 0.28080(12) 0.86417(6) 0.1142(4) Uani 1 1 d . . .
Cl2 Cl 0.10794(14) 0.33843(12) 0.05114(5) 0.1049(4) Uani 1 1 d . . .
F1 F 0.0468(2) 0.10196(16) 0.16110(11) 0.0785(5) Uani 1 1 d . . .
F2 F 0.3257(3) 0.26965(19) 0.92897(10) 0.0915(6) Uani 1 1 d . . .
N1 N 0.0870(3) 0.0711(2) 0.72469(12) 0.0555(6) Uani 1 1 d . . .
N2 N 0.3816(3) 0.3773(2) 0.30446(14) 0.0606(6) Uani 1 1 d . . .
O3 O 0.7089(2) 0.3391(2) 0.35805(12) 0.0766(6) Uani 1 1 d . . .
O4 O 0.5973(3) 0.1121(2) 0.33251(12) 0.0772(7) Uani 1 1 d . . .
O5 O -0.2598(2) 0.10602(18) 0.68191(12) 0.0665(5) Uani 1 1 d . . .
O6 O -0.1479(3) 0.32762(19) 0.73445(12) 0.0701(6) Uani 1 1 d . . .
S1 S 0.58102(8) 0.23627(7) 0.35666(4) 0.0564(2) Uani 1 1 d . . .
S2 S -0.12953(8) 0.21188(6) 0.69741(4) 0.0539(2) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.388(5) . ?
C1 C6 1.390(4) . ?
C1 Cl1 1.738(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.345(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 C7 1.487(4) . ?
C7 C8 1.390(4) . ?
C7 C12 1.375(4) . ?
C8 H8 0.9300 . ?
C8 N1 1.335(3) . ?
C10 C11 1.377(4) . ?
C10 N1 1.328(3) . ?
C10 S2 1.788(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(4) . ?
C12 F2 1.358(3) . ?
C13 C14 1.380(4) . ?
C13 C18 1.386(4) . ?
C13 S2 1.750(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(4) . ?
C16 C17 1.370(5) . ?
C16 C19 1.514(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(4) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.388(4) . ?
C20 C25 1.386(4) . ?
C20 Cl2 1.732(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.366(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.364(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(4) . ?
C25 C26 1.487(4) . ?
C26 C27 1.382(4) . ?
C26 C31 1.378(4) . ?
C27 H27 0.9300 . ?
C27 N2 1.330(3) . ?
C29 C30 1.380(4) . ?
C29 N2 1.321(3) . ?
C29 S1 1.794(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.374(4) . ?
C31 F1 1.348(3) . ?
C32 C33 1.386(4) . ?
C32 C37 1.375(4) . ?
C32 S1 1.742(2) . ?
C33 H33 0.9300 . ?
C33 C34 1.385(4) . ?
C34 H34 0.9300 . ?
C34 C35 1.379(4) . ?
C35 C36 1.371(4) . ?
C35 C38 1.513(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.388(4) . ?
C37 H37 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
O3 S1 1.436(2) . ?
O4 S1 1.437(2) . ?
O5 S2 1.433(2) . ?
O6 S2 1.433(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.5(4) . . ?
C2 C1 Cl1 118.5(3) . . ?
C6 C1 Cl1 120.0(3) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(4) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.7(4) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C7 122.3(3) . . ?
C5 C6 C1 117.3(3) . . ?
C5 C6 C7 120.4(3) . . ?
C8 C7 C6 120.1(3) . . ?
C12 C7 C6 124.7(3) . . ?
C12 C7 C8 115.2(3) . . ?
C7 C8 H8 117.6 . . ?
N1 C8 C7 124.8(3) . . ?
N1 C8 H8 117.6 . . ?
C11 C10 S2 120.0(2) . . ?
N1 C10 C11 125.2(2) . . ?
N1 C10 S2 114.8(2) . . ?
C10 C11 H11 122.1 . . ?
C12 C11 C10 115.8(3) . . ?
C12 C11 H11 122.1 . . ?
C11 C12 C7 122.9(3) . . ?
F2 C12 C7 119.0(3) . . ?
F2 C12 C11 118.1(3) . . ?
C14 C13 C18 120.4(3) . . ?
C14 C13 S2 120.3(2) . . ?
C18 C13 S2 119.3(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C19 120.3(3) . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 C19 120.9(3) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C13 C18 H18 120.6 . . ?
C17 C18 C13 118.8(3) . . ?
C17 C18 H18 120.6 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 Cl2 119.3(3) . . ?
C25 C20 C21 121.0(3) . . ?
C25 C20 Cl2 119.7(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(3) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(4) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 118.9 . . ?
C23 C24 C25 122.2(3) . . ?
C25 C24 H24 118.9 . . ?
C20 C25 C26 122.2(3) . . ?
C24 C25 C20 117.6(3) . . ?
C24 C25 C26 120.2(3) . . ?
C27 C26 C25 120.5(2) . . ?
C31 C26 C25 124.1(3) . . ?
C31 C26 C27 115.3(2) . . ?
C26 C27 H27 117.6 . . ?
N2 C27 C26 124.7(3) . . ?
N2 C27 H27 117.6 . . ?
C30 C29 S1 120.5(2) . . ?
N2 C29 C30 125.2(2) . . ?
N2 C29 S1 114.3(2) . . ?
C29 C30 H30 122.3 . . ?
C31 C30 C29 115.3(2) . . ?
C31 C30 H30 122.3 . . ?
C30 C31 C26 122.8(3) . . ?
F1 C31 C26 118.3(2) . . ?
F1 C31 C30 118.9(2) . . ?
C33 C32 S1 119.1(2) . . ?
C37 C32 C33 120.3(2) . . ?
C37 C32 S1 120.5(2) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 C32 118.7(3) . . ?
C34 C33 H33 120.6 . . ?
C33 C34 H34 119.1 . . ?
C35 C34 C33 121.8(3) . . ?
C35 C34 H34 119.1 . . ?
C34 C35 C38 120.5(3) . . ?
C36 C35 C34 118.4(3) . . ?
C36 C35 C38 121.1(3) . . ?
C35 C36 H36 119.4 . . ?
C35 C36 C37 121.2(3) . . ?
C37 C36 H36 119.4 . . ?
C32 C37 C36 119.6(3) . . ?
C32 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C10 N1 C8 116.2(2) . . ?
C29 N2 C27 116.7(2) . . ?
C32 S1 C29 103.59(11) . . ?
O3 S1 C29 107.24(13) . . ?
O3 S1 C32 108.72(13) . . ?
O3 S1 O4 119.99(14) . . ?
O4 S1 C29 106.82(13) . . ?
O4 S1 C32 109.23(13) . . ?
C13 S2 C10 103.94(12) . . ?
O5 S2 C10 107.26(12) . . ?
O5 S2 C13 109.06(14) . . ?
O6 S2 C10 106.38(13) . . ?
O6 S2 C13 109.01(13) . . ?
O6 S2 O5 119.99(13) . . ?

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
C1 C2 C3 C4 1.6(6) . . . . ?
C1 C6 C7 C8 118.5(3) . . . . ?
C1 C6 C7 C12 -63.2(4) . . . . ?
C2 C1 C6 C5 -2.6(5) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
C2 C3 C4 C5 -1.6(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C1 2.6(5) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C5 C6 C7 C8 -58.4(4) . . . . ?
C5 C6 C7 C12 119.9(4) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C6 C7 C8 N1 -179.7(3) . . . . ?
C6 C7 C12 C11 178.7(3) . . . . ?
C6 C7 C12 F2 -1.1(5) . . . . ?
C7 C8 N1 C10 -0.1(4) . . . . ?
C8 C7 C12 C11 -3.0(5) . . . . ?
C8 C7 C12 F2 177.2(3) . . . . ?
C10 C11 C12 C7 2.3(5) . . . . ?
C10 C11 C12 F2 -177.9(3) . . . . ?
C11 C10 N1 C8 -0.7(4) . . . . ?
C11 C10 S2 C13 120.1(2) . . . . ?
C11 C10 S2 O5 -124.4(2) . . . . ?
C11 C10 S2 O6 5.1(3) . . . . ?
C12 C7 C8 N1 1.9(4) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C13 C18 C17 0.5(4) . . . . ?
C14 C13 S2 C10 90.7(2) . . . . ?
C14 C13 S2 O5 -23.5(3) . . . . ?
C14 C13 S2 O6 -156.2(2) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C14 C15 C16 C19 179.1(3) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C13 -0.4(4) . . . . ?
C18 C13 C14 C15 -0.7(4) . . . . ?
C18 C13 S2 C10 -87.6(2) . . . . ?
C18 C13 S2 O5 158.2(2) . . . . ?
C18 C13 S2 O6 25.5(2) . . . . ?
C19 C16 C17 C18 -179.3(3) . . . . ?
C20 C21 C22 C23 0.8(6) . . . . ?
C20 C25 C26 C27 101.7(4) . . . . ?
C20 C25 C26 C31 -80.2(4) . . . . ?
C21 C20 C25 C24 0.6(5) . . . . ?
C21 C20 C25 C26 -176.8(3) . . . . ?
C21 C22 C23 C24 -0.4(6) . . . . ?
C22 C23 C24 C25 0.2(6) . . . . ?
C23 C24 C25 C20 -0.2(5) . . . . ?
C23 C24 C25 C26 177.1(3) . . . . ?
C24 C25 C26 C27 -75.5(4) . . . . ?
C24 C25 C26 C31 102.5(3) . . . . ?
C25 C20 C21 C22 -0.8(6) . . . . ?
C25 C26 C27 N2 178.0(3) . . . . ?
C25 C26 C31 C30 -177.0(2) . . . . ?
C25 C26 C31 F1 2.2(4) . . . . ?
C26 C27 N2 C29 -0.4(5) . . . . ?
C27 C26 C31 C30 1.1(4) . . . . ?
C27 C26 C31 F1 -179.7(2) . . . . ?
C29 C30 C31 C26 -1.3(4) . . . . ?
C29 C30 C31 F1 179.5(2) . . . . ?
C30 C29 N2 C27 0.1(4) . . . . ?
C30 C29 S1 C32 -103.4(2) . . . . ?
C30 C29 S1 O3 141.7(2) . . . . ?
C30 C29 S1 O4 11.9(3) . . . . ?
C31 C26 C27 N2 -0.2(4) . . . . ?
C32 C33 C34 C35 1.1(4) . . . . ?
C33 C32 C37 C36 0.6(4) . . . . ?
C33 C32 S1 C29 84.8(2) . . . . ?
C33 C32 S1 O3 -161.4(2) . . . . ?
C33 C32 S1 O4 -28.8(2) . . . . ?
C33 C34 C35 C36 -0.7(4) . . . . ?
C33 C34 C35 C38 -179.7(3) . . . . ?
C34 C35 C36 C37 0.3(4) . . . . ?
C35 C36 C37 C32 -0.2(4) . . . . ?
C37 C32 C33 C34 -1.0(4) . . . . ?
C37 C32 S1 C29 -93.6(2) . . . . ?
C37 C32 S1 O3 20.3(2) . . . . ?
C37 C32 S1 O4 152.9(2) . . . . ?
C38 C35 C36 C37 179.3(3) . . . . ?
Cl1 C1 C2 C3 -178.4(3) . . . . ?
Cl1 C1 C6 C5 176.3(2) . . . . ?
Cl1 C1 C6 C7 -0.6(4) . . . . ?
Cl2 C20 C21 C22 -179.7(3) . . . . ?
Cl2 C20 C25 C24 179.4(2) . . . . ?
Cl2 C20 C25 C26 2.1(4) . . . . ?
N1 C10 C11 C12 -0.3(4) . . . . ?
N1 C10 S2 C13 -59.1(2) . . . . ?
N1 C10 S2 O5 56.3(2) . . . . ?
N1 C10 S2 O6 -174.1(2) . . . . ?
N2 C29 C30 C31 0.7(4) . . . . ?
N2 C29 S1 C32 74.6(2) . . . . ?
N2 C29 S1 O3 -40.3(2) . . . . ?
N2 C29 S1 O4 -170.1(2) . . . . ?
S1 C29 C30 C31 178.53(19) . . . . ?
S1 C29 N2 C27 -177.8(2) . . . . ?
S1 C32 C33 C34 -179.3(2) . . . . ?
S1 C32 C37 C36 178.9(2) . . . . ?
S2 C10 C11 C12 -179.5(2) . . . . ?
S2 C10 N1 C8 178.5(2) . . . . ?
S2 C13 C14 C15 -178.9(2) . . . . ?
S2 C13 C18 C17 178.8(2) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.024
_oxdiff_exptl_absorpt_empirical_full_min 0.686

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

data_exp_18
_database_code_depnum_ccdc_archive 'CCDC 2076898'
loop_
_audit_author_name
_audit_author_address
'FengWanzhong p'
;shandong normal university
China
;
_audit_update_record             
;
2021-04-11 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2020-11-25
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H16 F N O4 S'
_chemical_formula_sum            'C20 H16 F N O4 S'
_chemical_formula_weight         385.40
_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'
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   6.0579(2)
_cell_length_b                   15.5439(5)
_cell_length_c                   9.8183(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.620(3)
_cell_angle_gamma                90.00
_cell_volume                     923.56(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6650
_cell_measurement_theta_min      10.1960
_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3793
_diffrn_reflns_theta_full        70.35
_diffrn_reflns_theta_max         70.36
_diffrn_reflns_theta_min         5.33
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9930
_diffrn_measured_fraction_theta_max 0.7265
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  24.00   1.00    1.00    --    0.00  81.00 117.00   26
  2  ω    -16.00  67.00   1.00    1.00    --   54.00 -81.00  -5.00   83
  3  ω    139.00 164.00   1.00    1.00    --  108.00  81.00 117.00   25
  4  ω    107.00 134.00   1.00    1.00    --  108.00 -81.00  -5.00   27
  5  ω     43.00  80.00   1.00    1.00    --  108.00 -81.00  -5.00   37
  6  ω    -21.00  29.00   1.00    1.00    --    0.00 -81.00  -5.00   50
  7  ω    -17.00  32.00   1.00    1.00    --    0.00  77.00-150.00   49
  8  ω     31.00  56.00   1.00    1.00    --   54.00  37.00 -60.00   25
  9  ω     38.00  64.00   1.00    1.00    --   54.00-125.00 -30.00   26
 10  ω      9.00  75.00   1.00    1.00    --   54.00 -37.00   0.00   66
 11  ω     91.00 120.00   1.00    1.00    --   54.00  37.00 -60.00   29
 12  ω    -17.00  76.00   1.00    1.00    --   54.00 -37.00 120.00   93
 13  ω     37.00  65.00   1.00    1.00    --  108.00-111.00 -60.00   28
 14  ω     37.00 109.00   1.00    1.00    --  108.00-111.00-180.00   72
 15  ω    116.00 160.00   1.00    1.00    --  108.00 111.00 -60.00   44
 16  ω     38.00 107.00   1.00    1.00    --  108.00-111.00 -30.00   69
 17  ω     54.00  99.00   1.00    1.00    --  108.00 -91.00  60.00   45
 18  ω     36.00  91.00   1.00    1.00    --  108.00 -91.00-120.00   55
 19  ω     87.00 171.00   1.00    1.00    --  108.00  37.00 150.00   84
 20  ω    104.00 134.00   1.00    1.00    --  108.00 111.00  30.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2108177000
_diffrn_orient_matrix_UB_12      -0.0484971000
_diffrn_orient_matrix_UB_13      -0.0369432000
_diffrn_orient_matrix_UB_21      -0.1426630000
_diffrn_orient_matrix_UB_22      -0.0701808000
_diffrn_orient_matrix_UB_23      -0.0714556000
_diffrn_orient_matrix_UB_31      0.0041088000
_diffrn_orient_matrix_UB_32      0.0504523000
_diffrn_orient_matrix_UB_33      -0.1349070000
_diffrn_oxdiff_digest_frames     
;
015f691d374eb623ece29f956535fcd821000286224
;
_diffrn_oxdiff_digest_hkl        
;
01b5a48ad5001fa4109ffec8960cc32ff09a41
;
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2476
_reflns_number_total             2576
_reflns_odcompleteness_completeness 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.029(18)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0350
_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     
'calc w=1/[σ²(Fo²)+(0.0601P)²+0.0140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C15(H15), C16(H16), C18(H18),
 C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1730(4) 0.8441(2) -0.3403(3) 0.0591(7) Uani 1 1 d . . .
H1 H -0.2743 0.8680 -0.2828 0.071 Uiso 1 1 calc R . .
C2 C -0.2270(6) 0.8355(3) -0.4779(3) 0.0751(10) Uani 1 1 d . . .
H2 H -0.3652 0.8530 -0.5127 0.090 Uiso 1 1 calc R . .
C3 C -0.0750(6) 0.8009(3) -0.5640(3) 0.0789(11) Uani 1 1 d . . .
H3 H -0.1104 0.7955 -0.6568 0.095 Uiso 1 1 calc R . .
C4 C 0.1260(7) 0.7747(2) -0.5123(3) 0.0755(10) Uani 1 1 d . . .
H4 H 0.2270 0.7512 -0.5704 0.091 Uiso 1 1 calc R . .
C5 C 0.1829(5) 0.7824(2) -0.3751(3) 0.0597(7) Uani 1 1 d . . .
H5 H 0.3211 0.7646 -0.3410 0.072 Uiso 1 1 calc R . .
C6 C 0.0310(4) 0.81732(18) -0.2879(2) 0.0470(6) Uani 1 1 d . . .
C7 C 0.0931(4) 0.83184(17) -0.1417(2) 0.0421(5) Uani 1 1 d . . .
C8 C -0.0108(4) 0.79497(18) -0.0322(2) 0.0444(5) Uani 1 1 d . . .
C9 C 0.1876(5) 0.8726(2) 0.1274(3) 0.0555(7) Uani 1 1 d . . .
H9 H 0.2136 0.8883 0.2181 0.067 Uiso 1 1 calc R . .
C10 C 0.3164(4) 0.91042(18) 0.0303(3) 0.0468(5) Uani 1 1 d . . .
C11 C 0.2612(4) 0.88879(17) -0.1036(2) 0.0457(6) Uani 1 1 d . . .
C12 C 0.5059(4) 0.9678(2) 0.0693(3) 0.0590(7) Uani 1 1 d . . .
C13 C 0.6932(7) 1.0410(4) 0.2485(5) 0.1015(15) Uani 1 1 d . . .
H13A H 0.8315 1.0200 0.2180 0.152 Uiso 1 1 calc R . .
H13B H 0.6985 1.0432 0.3463 0.152 Uiso 1 1 calc R . .
H13C H 0.6664 1.0977 0.2125 0.152 Uiso 1 1 calc R . .
C14 C -0.2118(4) 0.65886(16) 0.1016(3) 0.0451(6) Uani 1 1 d . . .
C15 C -0.0316(4) 0.60946(18) 0.1448(3) 0.0526(6) Uani 1 1 d . . .
H15 H 0.0867 0.6022 0.0888 0.063 Uiso 1 1 calc R . .
C16 C -0.0291(5) 0.5712(2) 0.2712(3) 0.0626(8) Uani 1 1 d . . .
H16 H 0.0925 0.5386 0.3008 0.075 Uiso 1 1 calc R . .
C17 C -0.2051(6) 0.5807(2) 0.3550(3) 0.0616(7) Uani 1 1 d . . .
C18 C -0.3857(5) 0.6288(2) 0.3079(3) 0.0622(8) Uani 1 1 d . . .
H18 H -0.5062 0.6345 0.3625 0.075 Uiso 1 1 calc R . .
C19 C -0.3910(4) 0.6683(2) 0.1821(3) 0.0545(7) Uani 1 1 d . . .
H19 H -0.5129 0.7007 0.1521 0.065 Uiso 1 1 calc R . .
C20 C -0.2024(8) 0.5389(4) 0.4939(4) 0.0951(13) Uani 1 1 d . . .
H20A H -0.0846 0.4976 0.5013 0.143 Uiso 1 1 calc R . .
H20B H -0.3408 0.5104 0.5056 0.143 Uiso 1 1 calc R . .
H20C H -0.1800 0.5821 0.5630 0.143 Uiso 1 1 calc R . .
F1 F 0.3753(2) 0.92314(12) -0.20305(15) 0.0571(4) Uani 1 1 d . . .
N1 N 0.0279(4) 0.81498(17) 0.0980(2) 0.0548(6) Uani 1 1 d . . .
O1 O -0.4256(3) 0.74655(15) -0.0887(2) 0.0659(6) Uani 1 1 d . . .
O2 O -0.1231(4) 0.65111(15) -0.1561(2) 0.0644(5) Uani 1 1 d . . .
O3 O 0.5158(4) 0.98371(18) 0.2008(2) 0.0795(7) Uani 1 1 d . . .
O4 O 0.6352(5) 0.9940(2) -0.0085(3) 0.1084(12) Uani 1 1 d . . .
S1 S -0.21092(9) 0.70934(4) -0.05917(6) 0.04718(16) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.381(4) . ?
C1 C6 1.381(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(3) . ?
C6 C7 1.485(3) . ?
C7 C8 1.394(3) . ?
C7 C11 1.388(3) . ?
C8 N1 1.326(3) . ?
C8 S1 1.811(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(4) . ?
C9 N1 1.340(4) . ?
C10 C11 1.383(4) . ?
C10 C12 1.490(4) . ?
C11 F1 1.334(3) . ?
C12 O3 1.313(4) . ?
C12 O4 1.191(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 O3 1.456(4) . ?
C14 C15 1.385(4) . ?
C14 C19 1.379(3) . ?
C14 S1 1.763(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 C18 1.386(5) . ?
C17 C20 1.510(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(4) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O1 S1 1.441(2) . ?
O2 S1 1.434(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C6 C1 C2 120.2(3) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 C7 119.8(2) . . ?
C5 C6 C7 120.5(2) . . ?
C8 C7 C6 125.5(2) . . ?
C11 C7 C6 120.5(2) . . ?
C11 C7 C8 114.0(2) . . ?
C7 C8 S1 120.80(19) . . ?
N1 C8 C7 125.5(2) . . ?
N1 C8 S1 113.66(18) . . ?
C10 C9 H9 118.1 . . ?
N1 C9 H9 118.1 . . ?
N1 C9 C10 123.9(2) . . ?
C9 C10 C12 121.8(2) . . ?
C11 C10 C9 115.5(2) . . ?
C11 C10 C12 122.7(2) . . ?
C10 C11 C7 123.6(2) . . ?
F1 C11 C7 117.2(2) . . ?
F1 C11 C10 119.2(2) . . ?
O3 C12 C10 111.4(2) . . ?
O4 C12 C10 124.2(3) . . ?
O4 C12 O3 124.4(3) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
C15 C14 S1 119.10(18) . . ?
C19 C14 C15 120.9(2) . . ?
C19 C14 S1 120.0(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 120.9(3) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 118.4(3) . . ?
C16 C17 C20 121.0(3) . . ?
C18 C17 C20 120.6(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.7(3) . . ?
C19 C18 H18 119.2 . . ?
C14 C19 H19 120.7 . . ?
C18 C19 C14 118.6(3) . . ?
C18 C19 H19 120.7 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 N1 C9 117.3(2) . . ?
C12 O3 C13 115.5(3) . . ?
C14 S1 C8 103.01(11) . . ?
O1 S1 C8 109.04(13) . . ?
O1 S1 C14 108.64(12) . . ?
O2 S1 C8 107.15(12) . . ?
O2 S1 C14 109.27(13) . . ?
O2 S1 O1 118.60(14) . . ?

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
C1 C2 C3 C4 0.6(6) . . . . ?
C1 C6 C7 C8 64.4(4) . . . . ?
C1 C6 C7 C11 -112.7(3) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
C2 C1 C6 C7 176.1(3) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C4 C5 C6 C7 -175.9(3) . . . . ?
C5 C6 C7 C8 -120.2(3) . . . . ?
C5 C6 C7 C11 62.7(4) . . . . ?
C6 C1 C2 C3 -0.8(5) . . . . ?
C6 C7 C8 N1 -172.1(3) . . . . ?
C6 C7 C8 S1 10.3(4) . . . . ?
C6 C7 C11 C10 174.9(2) . . . . ?
C6 C7 C11 F1 -5.9(3) . . . . ?
C7 C8 N1 C9 -3.3(4) . . . . ?
C7 C8 S1 C14 158.4(2) . . . . ?
C7 C8 S1 O1 -86.3(2) . . . . ?
C7 C8 S1 O2 43.2(2) . . . . ?
C8 C7 C11 C10 -2.6(4) . . . . ?
C8 C7 C11 F1 176.7(2) . . . . ?
C9 C10 C11 C7 -1.5(4) . . . . ?
C9 C10 C11 F1 179.2(2) . . . . ?
C9 C10 C12 O3 -6.7(4) . . . . ?
C9 C10 C12 O4 171.5(4) . . . . ?
C10 C9 N1 C8 -1.6(5) . . . . ?
C10 C12 O3 C13 -178.6(3) . . . . ?
C11 C7 C8 N1 5.2(4) . . . . ?
C11 C7 C8 S1 -172.39(19) . . . . ?
C11 C10 C12 O3 175.5(3) . . . . ?
C11 C10 C12 O4 -6.3(5) . . . . ?
C12 C10 C11 C7 176.4(2) . . . . ?
C12 C10 C11 F1 -2.9(4) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C15 C14 C19 C18 1.2(4) . . . . ?
C15 C14 S1 C8 -72.2(2) . . . . ?
C15 C14 S1 O1 172.2(2) . . . . ?
C15 C14 S1 O2 41.4(3) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
C15 C16 C17 C20 -179.9(3) . . . . ?
C16 C17 C18 C19 -1.3(5) . . . . ?
C17 C18 C19 C14 0.4(5) . . . . ?
C19 C14 C15 C16 -1.8(4) . . . . ?
C19 C14 S1 C8 108.3(2) . . . . ?
C19 C14 S1 O1 -7.3(3) . . . . ?
C19 C14 S1 O2 -138.1(2) . . . . ?
C20 C17 C18 C19 179.3(4) . . . . ?
N1 C8 S1 C14 -19.5(2) . . . . ?
N1 C8 S1 O1 95.8(2) . . . . ?
N1 C8 S1 O2 -134.7(2) . . . . ?
N1 C9 C10 C11 3.9(4) . . . . ?
N1 C9 C10 C12 -174.1(3) . . . . ?
O4 C12 O3 C13 3.2(6) . . . . ?
S1 C8 N1 C9 174.5(2) . . . . ?
S1 C14 C15 C16 178.8(2) . . . . ?
S1 C14 C19 C18 -179.3(2) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.814

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

data_exp_3690
_database_code_depnum_ccdc_archive 'CCDC 2076661'
loop_
_audit_author_name
_audit_author_address
'FengWanzhong c'
;shandong normal university
China
;
_audit_update_record             
;
2021-04-11 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H11 Cl F N O2'
_chemical_formula_sum            'C14 H11 Cl F N O2'
_chemical_formula_weight         279.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1 Cl1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.3135(7)
_cell_length_b                   7.6484(6)
_cell_length_c                   12.3996(11)
_cell_angle_alpha                103.627(7)
_cell_angle_beta                 97.874(8)
_cell_angle_gamma                98.131(7)
_cell_volume                     656.75(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1601
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8190
_cell_measurement_theta_min      6.2200
_exptl_absorpt_coefficient_mu    2.675
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3825
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.01
_diffrn_reflns_theta_min         3.73
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9868
_diffrn_measured_fraction_theta_max 0.9697
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00 -44.00   1.00    1.00    --    0.00 -37.00-150.00   26
  2  ω    -23.00  24.00   1.00    1.00    --    0.00 -37.00-150.00   47
  3  ω      5.00  58.00   1.00    1.00    --    0.00  57.00   0.00   53
  4  ω    -13.00  64.00   1.00    1.00    --   54.00 -57.00-180.00   77
  5  ω     23.00 102.00   1.00    1.00    --   54.00-125.00-180.00   79
  6  ω     72.00  98.00   1.00    1.00    --   54.00  57.00 120.00   26
  7  ω     75.00 100.00   1.00    1.00    --   54.00  57.00-150.00   25
  8  ω    -11.00  79.00   1.00    1.00    --   54.00 -77.00 -60.00   90
  9  ω     76.00 121.00   1.00    1.00    --   54.00  57.00 -30.00   45
 10  ω     28.00 121.00   1.00    1.00    --   54.00  37.00  90.00   93
 11  ω     41.00 129.00   1.00    1.00    --  108.00 -50.00 120.00   88
 12  ω     36.00 109.00   1.00    1.00    --  108.00-111.00 -30.00   73
 13  ω     85.00 151.00   1.00    1.00    --  108.00  37.00-120.00   66
 14  ω     39.00  74.00   1.00    1.00    --  108.00 -91.00 150.00   35
 15  ω    138.00 169.00   1.00    1.00    --  108.00  63.00 -90.00   31
 16  ω     86.00 121.00   1.00    1.00    --  108.00  63.00 -90.00   35
 17  ω     54.00 120.00   1.00    1.00    --  108.00 -77.00 -30.00   66
 18  ω     63.00 133.00   1.00    1.00    --  108.00 -37.00 -30.00   70
 19  ω     36.00 133.00   1.00    1.00    --  108.00 -37.00 -90.00   97
 20  ω     52.00 112.00   1.00    1.00    --  108.00-111.00 120.00   60
 21  ω    142.00 177.00   1.00    1.00    --  108.00  25.00  90.00   35
 22  ω    101.00 127.00   1.00    1.00    --  108.00 111.00 -30.00   26
 23  ω     82.00 143.00   1.00    1.00    --  108.00 -91.00 150.00   61
 24  ω    115.00 171.00   1.00    1.00    --  108.00  37.00 -30.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2082058000
_diffrn_orient_matrix_UB_12      -0.0189862000
_diffrn_orient_matrix_UB_13      0.0171620000
_diffrn_orient_matrix_UB_21      -0.0206459000
_diffrn_orient_matrix_UB_22      -0.0561415000
_diffrn_orient_matrix_UB_23      0.1097753000
_diffrn_orient_matrix_UB_31      -0.0544686000
_diffrn_orient_matrix_UB_32      -0.2022092000
_diffrn_orient_matrix_UB_33      -0.0672836000
_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'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1864
_reflns_number_total             2312
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0814P)²+0.1469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1547
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4142(3) 0.3987(3) 0.7589(2) 0.0611(6) Uani 1 1 d . . .
H1 H 0.5147 0.3409 0.7741 0.073 Uiso 1 1 calc R . .
C2 C 0.4128(4) 0.4939(4) 0.6776(2) 0.0672(7) Uani 1 1 d . . .
H2 H 0.5124 0.5020 0.6386 0.081 Uiso 1 1 calc R . .
C3 C 0.2622(4) 0.5771(3) 0.65461(19) 0.0611(6) Uani 1 1 d . . .
C4 C 0.1172(4) 0.5735(3) 0.7139(2) 0.0637(6) Uani 1 1 d . . .
H4 H 0.0183 0.6334 0.6988 0.076 Uiso 1 1 calc R . .
C5 C 0.1205(3) 0.4794(3) 0.7963(2) 0.0592(6) Uani 1 1 d . . .
H5 H 0.0232 0.4774 0.8373 0.071 Uiso 1 1 calc R . .
C6 C 0.2666(3) 0.3876(3) 0.81901(18) 0.0519(5) Uani 1 1 d . . .
C7 C 0.2617(3) 0.2802(3) 0.90350(19) 0.0514(5) Uani 1 1 d . . .
C8 C 0.2853(3) 0.1003(3) 0.88227(19) 0.0564(6) Uani 1 1 d . . .
C9 C 0.2719(3) 0.0008(3) 0.9598(2) 0.0572(6) Uani 1 1 d . . .
H9 H 0.2859 -0.1211 0.9432 0.069 Uiso 1 1 calc R . .
C10 C 0.2367(3) 0.0878(3) 1.06379(19) 0.0517(5) Uani 1 1 d . . .
C11 C 0.2260(4) 0.3522(3) 1.01120(19) 0.0575(6) Uani 1 1 d . . .
H11 H 0.2097 0.4735 1.0293 0.069 Uiso 1 1 calc R . .
C12 C 0.2260(3) -0.0192(3) 1.1499(2) 0.0590(6) Uani 1 1 d . . .
C13 C 0.2048(7) -0.0147(4) 1.3394(3) 0.1024(12) Uani 1 1 d . . .
H13A H 0.0905 -0.1045 1.3248 0.123 Uiso 1 1 calc R . .
H13B H 0.3106 -0.0779 1.3425 0.123 Uiso 1 1 calc R . .
C14 C 0.2172(6) 0.1161(5) 1.4439(3) 0.1044(12) Uani 1 1 d . . .
H14A H 0.3234 0.2116 1.4542 0.157 Uiso 1 1 calc R . .
H14B H 0.2318 0.0575 1.5043 0.157 Uiso 1 1 calc R . .
H14C H 0.1047 0.1674 1.4438 0.157 Uiso 1 1 calc R . .
Cl1 Cl 0.25497(13) 0.68525(11) 0.54539(6) 0.0911(4) Uani 1 1 d . . .
N1 N 0.2133(3) 0.2623(2) 1.09026(16) 0.0579(5) Uani 1 1 d . . .
O1 O 0.2377(3) -0.1786(2) 1.13029(17) 0.0782(6) Uani 1 1 d . . .
O2 O 0.2046(3) 0.0784(2) 1.24868(15) 0.0768(6) Uani 1 1 d . . .
F1 F 0.3180(3) 0.01702(19) 0.77951(13) 0.0827(5) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.376(4) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C3 C4 1.371(4) . ?
C3 Cl1 1.744(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(3) . ?
C6 C7 1.477(3) . ?
C7 C8 1.379(3) . ?
C7 C11 1.394(3) . ?
C8 C9 1.365(3) . ?
C8 F1 1.353(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(3) . ?
C10 C12 1.494(3) . ?
C10 N1 1.339(3) . ?
C11 H11 0.9300 . ?
C11 N1 1.329(3) . ?
C12 O1 1.203(3) . ?
C12 O2 1.319(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.421(4) . ?
C13 O2 1.466(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C2 C1 H1 119.5 . . ?
C2 C1 C6 120.9(2) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 Cl1 118.8(2) . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 Cl1 119.6(2) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.9(2) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 121.8(2) . . ?
C5 C6 C1 118.1(2) . . ?
C5 C6 C7 120.1(2) . . ?
C8 C7 C6 123.5(2) . . ?
C8 C7 C11 114.4(2) . . ?
C11 C7 C6 122.12(19) . . ?
C9 C8 C7 122.6(2) . . ?
F1 C8 C7 118.9(2) . . ?
F1 C8 C9 118.45(19) . . ?
C8 C9 H9 121.2 . . ?
C8 C9 C10 117.56(19) . . ?
C10 C9 H9 121.2 . . ?
C9 C10 C12 117.80(19) . . ?
N1 C10 C9 122.9(2) . . ?
N1 C10 C12 119.3(2) . . ?
C7 C11 H11 117.2 . . ?
N1 C11 C7 125.5(2) . . ?
N1 C11 H11 117.2 . . ?
O1 C12 C10 122.8(2) . . ?
O1 C12 O2 123.8(2) . . ?
O2 C12 C10 113.42(19) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C14 C13 O2 109.4(2) . . ?
O2 C13 H13A 109.8 . . ?
O2 C13 H13B 109.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 N1 C10 116.98(19) . . ?
C12 O2 C13 116.5(2) . . ?

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
C1 C2 C3 C4 2.6(4) . . . . ?
C1 C2 C3 Cl1 -176.05(18) . . . . ?
C1 C6 C7 C8 -51.2(3) . . . . ?
C1 C6 C7 C11 131.0(2) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C1 C6 C7 177.6(2) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C1 2.3(3) . . . . ?
C4 C5 C6 C7 -176.8(2) . . . . ?
C5 C6 C7 C8 127.9(2) . . . . ?
C5 C6 C7 C11 -49.9(3) . . . . ?
C6 C1 C2 C3 -0.8(4) . . . . ?
C6 C7 C8 C9 -177.0(2) . . . . ?
C6 C7 C8 F1 1.1(3) . . . . ?
C6 C7 C11 N1 177.7(2) . . . . ?
C7 C8 C9 C10 -1.3(4) . . . . ?
C7 C11 N1 C10 0.0(4) . . . . ?
C8 C7 C11 N1 -0.3(4) . . . . ?
C8 C9 C10 C12 -178.7(2) . . . . ?
C8 C9 C10 N1 0.9(3) . . . . ?
C9 C10 C12 O1 -3.6(4) . . . . ?
C9 C10 C12 O2 175.7(2) . . . . ?
C9 C10 N1 C11 -0.3(3) . . . . ?
C10 C12 O2 C13 -176.3(3) . . . . ?
C11 C7 C8 C9 1.0(3) . . . . ?
C11 C7 C8 F1 179.1(2) . . . . ?
C12 C10 N1 C11 179.3(2) . . . . ?
C14 C13 O2 C12 168.8(3) . . . . ?
Cl1 C3 C4 C5 176.78(18) . . . . ?
N1 C10 C12 O1 176.7(2) . . . . ?
N1 C10 C12 O2 -3.9(3) . . . . ?
O1 C12 O2 C13 3.0(4) . . . . ?
F1 C8 C9 C10 -179.4(2) . . . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.670
_oxdiff_exptl_absorpt_empirical_full_min 0.675

