# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2149790'
loop_
_audit_author_name
_audit_author_address
'Ai Ito'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;
_audit_creation_date             2021-12-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C21 H16 F5 N2 O, 0.5(H2 O)'
_chemical_formula_sum            'C21 H17 Cl F5 N2 O1.50'
_chemical_formula_weight         451.82
_chemical_absolute_configuration ?
_chemical_melting_point          439-441
_chemical_oxdiff_formula         C21H16Cl1F5N2O1
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'
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'
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'

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

_cell_length_a                   9.0543(2)
_cell_length_b                   13.0350(2)
_cell_length_c                   34.3367(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4052.51(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7141
_cell_measurement_temperature    93
_cell_measurement_theta_max      76.3550
_cell_measurement_theta_min      2.5630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.34a (Rigaku Oxford Diffraction, 2019)
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    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1848
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 1 4 0.1451
0 8 5 0.0335
0 0 22 0.0039
0 -8 -6 0.0558
-1 8 6 0.0281
-6 -1 4 0.0985
1 8 1 0.0500
0 0 -22 0.0231
0 -8 -6 0.0507
0 8 6 0.0363
6 2 -5 0.1392
-3 0 -19 0.0719

_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.031
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.7141 1.4310 3.6421 -0.0247 -0.9526 -0.3031
-0.0888 8.2800 4.6044 0.0043 0.1224 -0.9925
0.0239 0.2764 22.2690 0.9597 -0.1262 -0.2511
0.3125 -8.1810 -5.5876 -0.0551 -0.1526 0.9868
-0.6009 8.1296 5.7646 0.0715 0.1989 -0.9774
-5.7775 -0.5097 3.8850 0.3312 0.9353 0.1247
0.6350 8.3983 1.3373 -0.1593 0.0219 -0.9870
0.0268 0.3950 -22.2554 -0.9765 0.1285 0.1731
-0.0415 -8.1969 -5.5506 -0.0439 -0.0939 0.9946
0.0857 8.2010 5.5018 0.0406 0.0868 -0.9954
5.5881 1.6495 -5.3817 -0.4185 -0.8767 -0.2371
-2.8716 -0.1083 -19.4407 -0.7668 0.5888 0.2555

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            15075
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.772
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_temperature      93
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -15.00   0.50    1.25    --  -43.55 -19.00  62.00  166
  2  ω   -156.00-129.00   0.50    5.01    --  -97.00-109.00 -55.00   54
  3  ω   -154.00 -94.00   0.50    5.01    --  -97.00-121.00-140.00  120
  4  ω     89.00 173.00   0.50    5.01    --  113.46  19.00-129.00  168
  5  ω   -112.00 -63.00   0.50    1.25    --  -43.55-179.00-150.00   98
  6  ω    -29.00  22.00   0.50    1.25    --   43.55 -19.00 -60.00  102
  7  ω    -54.00 -23.00   0.50    5.01    --  -97.00  45.00-150.00   62
  8  ω    -57.00 -32.00   0.50    5.01    --  -97.00  61.00-150.00   50
  9  ω     41.00  67.00   0.50    5.01    --  113.46 -61.00-150.00   52
 10  ω     41.00  67.00   0.50    5.01    --  113.46 -94.00-120.00   52
 11  ω     52.00 100.00   0.50    5.01    --  113.46 -94.00 -60.00   96
 12  ω     42.00  67.00   0.50    5.01    --  113.46 -61.00  30.00   50
 13  ω     45.00  81.00   0.50    5.01    --  113.46 -94.00 -30.00   72
 14  ω     80.00 105.00   0.50    5.01    --  113.46 -94.00-120.00   50
 15  ω     40.00  68.00   0.50    5.01    --  113.46 -61.00-180.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0260127000
_diffrn_orient_matrix_UB_12      -0.0239109000
_diffrn_orient_matrix_UB_13      0.0434209000
_diffrn_orient_matrix_UB_21      -0.1671380000
_diffrn_orient_matrix_UB_22      0.0161505000
_diffrn_orient_matrix_UB_23      -0.0056881000
_diffrn_orient_matrix_UB_31      -0.0180783000
_diffrn_orient_matrix_UB_32      -0.1145903000
_diffrn_orient_matrix_UB_33      -0.0098327000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_reflns_Friedel_coverage         0.619
_reflns_Friedel_fraction_full    0.843
_reflns_Friedel_fraction_max     0.757
_reflns_number_gt                6611
_reflns_number_total             7498
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.41.34a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.34a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.34a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 2202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.394(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     557
_refine_ls_number_reflns         7498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.117
_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)+(0.0168P)²+8.6529P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1323
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 N4(H4), N2(H2)
2.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C37(H37), C30(H30), C13(H13), C16(H16), C15(H15), C9(H9), C19(H19),
 C18(H18), C39(H39), C12(H12), C10(H10), C40(H40), C11(H11), C34(H34), C31(H31),
  C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C42(H42A,H42B,
 H42C)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl2 Cl 0.82642(17) 1.10854(10) 0.53871(4) 0.0302(3) Uani 1 1 d . . . . .
Cl1 Cl 0.33406(17) 0.19610(9) 0.05823(4) 0.0302(3) Uani 1 1 d . . . . .
F8 F 0.8272(5) 0.4899(2) 0.22627(10) 0.0372(8) Uani 1 1 d . . . . .
F5 F 0.8041(4) 0.8927(3) 0.15778(10) 0.0426(9) Uani 1 1 d . . . . .
F1 F 0.4800(4) 0.7177(3) 0.24156(10) 0.0382(9) Uani 1 1 d . . . . .
F9 F 1.0430(4) 0.6297(3) 0.21480(10) 0.0381(8) Uani 1 1 d . . . . .
F10 F 1.0755(4) 0.7888(3) 0.26417(11) 0.0392(9) Uani 1 1 d . . . . .
F6 F 0.6774(4) 0.6655(3) 0.33865(10) 0.0418(9) Uani 1 1 d . . . . .
F2 F 0.4835(4) 0.8772(3) 0.29133(10) 0.0422(9) Uani 1 1 d . . . . .
F3 F 0.6508(5) 1.0438(2) 0.27504(11) 0.0466(10) Uani 1 1 d . . . . .
F7 F 0.6415(4) 0.5095(3) 0.28772(11) 0.0445(10) Uani 1 1 d . . . . .
F4 F 0.8114(6) 1.0517(3) 0.20832(12) 0.0573(12) Uani 1 1 d . . . . .
O3 O 0.3413(5) -0.0291(3) 0.02134(13) 0.0331(9) Uani 1 1 d G . . . .
H3A H 0.334843 0.032118 0.029713 0.050 Uiso 1 1 d G U . . .
H3B H 0.427166 -0.048545 0.028088 0.050 Uiso 1 1 d G U . . .
O1 O 0.7527(5) 0.6553(3) 0.17011(13) 0.0394(11) Uani 1 1 d . . . . .
O2 O 0.7852(5) 0.8919(4) 0.32269(13) 0.0464(13) Uani 1 1 d . . . . .
N3 N 0.9765(5) 0.8295(3) 0.35770(13) 0.0210(9) Uani 1 1 d . . . . .
N4 N 0.9095(5) 1.1712(3) 0.45753(14) 0.0222(9) Uani 1 1 d . . . . .
H4 H 0.884953 1.143351 0.483884 0.027 Uiso 1 1 calc R U . . .
N1 N 0.5271(5) 0.7007(3) 0.14707(13) 0.0216(9) Uani 1 1 d . . . . .
N2 N 0.5432(5) 0.3706(3) 0.03964(14) 0.0245(9) Uani 1 1 d . . . . .
H2 H 0.472000 0.317866 0.049413 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5278(6) 0.6161(4) 0.11918(15) 0.0223(10) Uani 1 1 d . . . . .
C35 C 0.9693(6) 0.9167(4) 0.38397(15) 0.0221(11) Uani 1 1 d . . . . .
C38 C 0.9393(6) 1.0822(4) 0.43203(15) 0.0218(11) Uani 1 1 d . . . . .
C6 C 0.6414(6) 0.8021(4) 0.19833(16) 0.0231(11) Uani 1 1 d . . . . .
C36 C 0.9213(6) 0.9019(4) 0.42155(16) 0.0239(11) Uani 1 1 d . . . . .
H36 H 0.900108 0.834672 0.430682 0.029 Uiso 1 1 calc R U . . .
C17 C 0.5360(6) 0.4582(4) 0.06699(16) 0.0236(11) Uani 1 1 d . . . . .
C27 C 0.8764(6) 0.7308(4) 0.30280(16) 0.0215(11) Uani 1 1 d . . . . .
C29 C 1.0835(6) 0.7506(4) 0.36581(16) 0.0234(11) Uani 1 1 d . . . . .
C37 C 0.9043(6) 0.9853(4) 0.44592(16) 0.0252(11) Uani 1 1 d . . . . .
H37 H 0.869098 0.976409 0.471771 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4073(6) 0.7742(4) 0.14551(16) 0.0216(11) Uani 1 1 d . . . . .
C7 C 0.6455(6) 0.7114(4) 0.17075(16) 0.0255(12) Uani 1 1 d . . . . .
C30 C 1.0429(7) 0.6664(4) 0.38822(17) 0.0268(12) Uani 1 1 d . . . . .
H30 H 0.943579 0.657413 0.396479 0.032 Uiso 1 1 calc R U . . .
C2 C 0.5644(6) 0.8801(4) 0.25869(17) 0.0272(12) Uani 1 1 d . . . . .
C13 C 0.4253(6) 0.8646(4) 0.12447(16) 0.0243(11) Uani 1 1 d . . . . .
H13 H 0.515945 0.878695 0.111611 0.029 Uiso 1 1 calc R U . . .
C16 C 0.4562(7) 0.4471(4) 0.10109(16) 0.0271(12) Uani 1 1 d . . . . .
H16 H 0.404740 0.385053 0.106295 0.033 Uiso 1 1 calc R U . . .
C23 C 0.7491(6) 0.5777(4) 0.28239(17) 0.0268(12) Uani 1 1 d . . . . .
C15 C 0.4522(7) 0.5271(4) 0.12755(16) 0.0269(12) Uani 1 1 d . . . . .
H15 H 0.398024 0.520790 0.151132 0.032 Uiso 1 1 calc R U . . .
C25 C 0.9513(6) 0.6395(4) 0.24501(16) 0.0256(12) Uani 1 1 d . . . . .
C24 C 0.8430(7) 0.5681(4) 0.25080(16) 0.0253(11) Uani 1 1 d . . . . .
C26 C 0.9672(6) 0.7199(4) 0.27085(16) 0.0252(11) Uani 1 1 d . . . . .
C9 C 0.2757(6) 0.7523(4) 0.16424(17) 0.0264(12) Uani 1 1 d . . . . .
H9 H 0.264312 0.690375 0.178509 0.032 Uiso 1 1 calc R U . . .
C19 C 0.6068(6) 0.6280(4) 0.08486(17) 0.0264(12) Uani 1 1 d . . . . .
H19 H 0.657433 0.690333 0.079622 0.032 Uiso 1 1 calc R U . . .
C22 C 0.7678(6) 0.6576(4) 0.30801(16) 0.0256(12) Uani 1 1 d . . . . .
C1 C 0.5620(6) 0.7997(4) 0.23279(17) 0.0262(12) Uani 1 1 d . . . . .
C18 C 0.6110(6) 0.5476(4) 0.05815(18) 0.0276(12) Uani 1 1 d . . . . .
H18 H 0.664158 0.553987 0.034429 0.033 Uiso 1 1 calc R U . . .
C41 C 0.7780(7) 1.2304(4) 0.44404(18) 0.0305(12) Uani 1 1 d . . . . .
H41A H 0.794120 1.253811 0.417255 0.046 Uiso 1 1 calc R U . . .
H41B H 0.763232 1.289929 0.461049 0.046 Uiso 1 1 calc R U . . .
H41C H 0.690317 1.186415 0.444975 0.046 Uiso 1 1 calc R U . . .
C39 C 0.9931(7) 1.0971(4) 0.39481(16) 0.0281(12) Uani 1 1 d . . . . .
H39 H 1.018801 1.163817 0.385979 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3091(7) 0.9339(4) 0.12252(17) 0.0280(12) Uani 1 1 d . . . . .
H12 H 0.320085 0.995926 0.108312 0.034 Uiso 1 1 calc R U . . .
C28 C 0.8764(6) 0.8249(4) 0.32855(16) 0.0256(12) Uani 1 1 d . . . . .
C5 C 0.7266(6) 0.8873(5) 0.19117(16) 0.0299(12) Uani 1 1 d . . . . .
C10 C 0.1607(8) 0.8223(4) 0.16184(17) 0.0329(13) Uani 1 1 d . . . . .
H10 H 0.069624 0.808091 0.174472 0.039 Uiso 1 1 calc R U . . .
C3 C 0.6511(8) 0.9648(4) 0.25059(17) 0.0310(13) Uani 1 1 d . . . . .
C40 C 1.0087(6) 1.0124(4) 0.37053(16) 0.0258(12) Uani 1 1 d . . . . .
H40 H 1.046341 1.020502 0.344887 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1775(7) 0.9127(4) 0.14120(17) 0.0321(13) Uani 1 1 d . . . . .
H11 H 0.098278 0.960384 0.139872 0.039 Uiso 1 1 calc R U . . .
C34 C 1.2273(7) 0.7645(5) 0.35363(19) 0.0335(14) Uani 1 1 d . . . . .
H34 H 1.253207 0.822612 0.338393 0.040 Uiso 1 1 calc R U . . .
C21 C 0.4959(7) 0.3976(5) -0.00085(16) 0.0324(13) Uani 1 1 d . . . . .
H21A H 0.397704 0.429228 -0.000068 0.049 Uiso 1 1 calc R U . . .
H21B H 0.492235 0.335309 -0.016791 0.049 Uiso 1 1 calc R U . . .
H21C H 0.566657 0.446004 -0.012185 0.049 Uiso 1 1 calc R U . . .
C31 C 1.1524(8) 0.5948(4) 0.39836(19) 0.0388(15) Uani 1 1 d . . . . .
H31 H 1.127246 0.536107 0.413341 0.047 Uiso 1 1 calc R U . . .
C20 C 0.6928(7) 0.3217(4) 0.03986(18) 0.0319(13) Uani 1 1 d . . . . .
H20A H 0.765662 0.370082 0.029502 0.048 Uiso 1 1 calc R U . . .
H20B H 0.691095 0.259855 0.023619 0.048 Uiso 1 1 calc R U . . .
H20C H 0.719463 0.303051 0.066600 0.048 Uiso 1 1 calc R U . . .
C4 C 0.7307(8) 0.9690(4) 0.21643(19) 0.0374(15) Uani 1 1 d . . . . .
C42 C 1.0396(6) 1.2398(4) 0.46244(19) 0.0304(12) Uani 1 1 d . . . . .
H42A H 1.127145 1.198510 0.468422 0.046 Uiso 1 1 calc R U . . .
H42B H 1.021052 1.287928 0.483827 0.046 Uiso 1 1 calc R U . . .
H42C H 1.056326 1.278255 0.438306 0.046 Uiso 1 1 calc R U . . .
C32 C 1.2953(8) 0.6097(5) 0.3866(2) 0.0436(17) Uani 1 1 d . . . . .
H32 H 1.369039 0.562037 0.394372 0.052 Uiso 1 1 calc R U . . .
C33 C 1.3344(7) 0.6925(6) 0.3639(2) 0.0470(18) Uani 1 1 d . . . . .
H33 H 1.433461 0.700372 0.355241 0.056 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
F8 C24 1.330(6) . ?
F5 C5 1.346(7) . ?
F1 C1 1.335(7) . ?
F9 C25 1.335(6) . ?
F10 C26 1.350(6) . ?
F6 C22 1.337(6) . ?
F2 C2 1.339(7) . ?
F3 C3 1.329(6) . ?
F7 C23 1.332(6) . ?
F4 C4 1.332(7) . ?
O3 H3A 0.8498 . ?
O3 H3B 0.8504 . ?
O1 C7 1.215(7) . ?
O2 C28 1.218(7) . ?
N3 C35 1.452(6) . ?
N3 C29 1.440(7) . ?
N3 C28 1.352(7) . ?
N4 H4 1.0000 . ?
N4 C38 1.478(7) . ?
N4 C41 1.492(7) . ?
N4 C42 1.489(7) . ?
N1 C14 1.461(6) . ?
N1 C8 1.448(7) . ?
N1 C7 1.352(7) . ?
N2 H2 1.0000 . ?
N2 C17 1.480(7) . ?
N2 C21 1.497(7) . ?
N2 C20 1.497(7) . ?
C14 C15 1.377(8) . ?
C14 C19 1.387(7) . ?
C35 C36 1.375(8) . ?
C35 C40 1.378(7) . ?
C38 C37 1.387(7) . ?
C38 C39 1.381(8) . ?
C6 C7 1.515(7) . ?
C6 C1 1.385(8) . ?
C6 C5 1.375(8) . ?
C36 H36 0.9500 . ?
C36 C37 1.381(8) . ?
C17 C16 1.383(8) . ?
C17 C18 1.382(8) . ?
C27 C26 1.378(8) . ?
C27 C22 1.381(8) . ?
C27 C28 1.512(7) . ?
C29 C30 1.390(8) . ?
C29 C34 1.380(8) . ?
C37 H37 0.9500 . ?
C8 C13 1.391(7) . ?
C8 C9 1.384(8) . ?
C30 H30 0.9500 . ?
C30 C31 1.405(8) . ?
C2 C1 1.375(8) . ?
C2 C3 1.383(9) . ?
C13 H13 0.9500 . ?
C13 C12 1.388(8) . ?
C16 H16 0.9500 . ?
C16 C15 1.384(8) . ?
C23 C24 1.384(8) . ?
C23 C22 1.375(8) . ?
C15 H15 0.9500 . ?
C25 C24 1.366(8) . ?
C25 C26 1.380(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(8) . ?
C19 H19 0.9500 . ?
C19 C18 1.394(8) . ?
C18 H18 0.9500 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C39 H39 0.9500 . ?
C39 C40 1.391(8) . ?
C12 H12 0.9500 . ?
C12 C11 1.381(9) . ?
C5 C4 1.374(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(8) . ?
C3 C4 1.378(10) . ?
C40 H40 0.9500 . ?
C11 H11 0.9500 . ?
C34 H34 0.9500 . ?
C34 C33 1.395(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 H31 0.9500 . ?
C31 C32 1.369(10) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C32 H32 0.9500 . ?
C32 C33 1.379(11) . ?
C33 H33 0.9500 . ?

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
H3A O3 H3B 104.5 . . ?
C29 N3 C35 118.0(4) . . ?
C28 N3 C35 117.7(4) . . ?
C28 N3 C29 124.2(4) . . ?
C38 N4 H4 106.9 . . ?
C38 N4 C41 111.6(4) . . ?
C38 N4 C42 113.2(4) . . ?
C41 N4 H4 106.9 . . ?
C42 N4 H4 106.9 . . ?
C42 N4 C41 110.8(4) . . ?
C8 N1 C14 118.6(4) . . ?
C7 N1 C14 118.0(4) . . ?
C7 N1 C8 123.2(4) . . ?
C17 N2 H2 106.8 . . ?
C17 N2 C21 113.3(4) . . ?
C17 N2 C20 111.4(4) . . ?
C21 N2 H2 106.8 . . ?
C20 N2 H2 106.8 . . ?
C20 N2 C21 111.3(5) . . ?
C15 C14 N1 119.8(5) . . ?
C15 C14 C19 121.9(5) . . ?
C19 C14 N1 118.3(5) . . ?
C36 C35 N3 119.2(5) . . ?
C36 C35 C40 121.5(5) . . ?
C40 C35 N3 119.3(5) . . ?
C37 C38 N4 118.0(5) . . ?
C39 C38 N4 120.1(5) . . ?
C39 C38 C37 121.8(5) . . ?
C1 C6 C7 121.9(5) . . ?
C5 C6 C7 120.3(5) . . ?
C5 C6 C1 117.6(5) . . ?
C35 C36 H36 120.2 . . ?
C35 C36 C37 119.6(5) . . ?
C37 C36 H36 120.2 . . ?
C16 C17 N2 118.6(5) . . ?
C18 C17 N2 119.3(5) . . ?
C18 C17 C16 122.1(5) . . ?
C26 C27 C22 117.1(5) . . ?
C26 C27 C28 123.3(5) . . ?
C22 C27 C28 119.0(5) . . ?
C30 C29 N3 119.6(5) . . ?
C34 C29 N3 118.9(5) . . ?
C34 C29 C30 121.4(5) . . ?
C38 C37 H37 120.6 . . ?
C36 C37 C38 118.9(5) . . ?
C36 C37 H37 120.6 . . ?
C13 C8 N1 119.5(5) . . ?
C9 C8 N1 119.4(5) . . ?
C9 C8 C13 121.1(5) . . ?
O1 C7 N1 124.0(5) . . ?
O1 C7 C6 120.0(5) . . ?
N1 C7 C6 115.9(5) . . ?
C29 C30 H30 120.8 . . ?
C29 C30 C31 118.3(6) . . ?
C31 C30 H30 120.8 . . ?
F2 C2 C1 120.8(5) . . ?
F2 C2 C3 120.0(5) . . ?
C1 C2 C3 119.2(5) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 C8 119.2(5) . . ?
C12 C13 H13 120.4 . . ?
C17 C16 H16 120.3 . . ?
C17 C16 C15 119.4(5) . . ?
C15 C16 H16 120.3 . . ?
F7 C23 C24 119.8(5) . . ?
F7 C23 C22 120.6(5) . . ?
C22 C23 C24 119.6(5) . . ?
C14 C15 C16 119.0(5) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
F9 C25 C24 119.6(5) . . ?
F9 C25 C26 120.5(5) . . ?
C24 C25 C26 119.9(5) . . ?
F8 C24 C23 120.0(5) . . ?
F8 C24 C25 120.5(5) . . ?
C25 C24 C23 119.6(5) . . ?
F10 C26 C27 120.0(5) . . ?
F10 C26 C25 118.1(5) . . ?
C27 C26 C25 121.9(5) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.9(5) . . ?
C10 C9 H9 120.6 . . ?
C14 C19 H19 120.4 . . ?
C14 C19 C18 119.3(5) . . ?
C18 C19 H19 120.4 . . ?
F6 C22 C27 119.0(5) . . ?
F6 C22 C23 119.1(5) . . ?
C23 C22 C27 121.9(5) . . ?
F1 C1 C6 120.0(5) . . ?
F1 C1 C2 118.2(5) . . ?
C2 C1 C6 121.8(5) . . ?
C17 C18 C19 118.4(5) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
N4 C41 H41A 109.5 . . ?
N4 C41 H41B 109.5 . . ?
N4 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C39 H39 120.7 . . ?
C38 C39 C40 118.6(5) . . ?
C40 C39 H39 120.7 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 119.9 . . ?
O2 C28 N3 123.0(5) . . ?
O2 C28 C27 119.0(5) . . ?
N3 C28 C27 118.0(5) . . ?
F5 C5 C6 119.2(5) . . ?
F5 C5 C4 118.9(6) . . ?
C4 C5 C6 121.9(6) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(6) . . ?
C11 C10 H10 119.7 . . ?
F3 C3 C2 119.4(6) . . ?
F3 C3 C4 120.5(6) . . ?
C4 C3 C2 120.0(5) . . ?
C35 C40 C39 119.5(5) . . ?
C35 C40 H40 120.3 . . ?
C39 C40 H40 120.3 . . ?
C12 C11 C10 120.2(6) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C29 C34 H34 120.3 . . ?
C29 C34 C33 119.4(6) . . ?
C33 C34 H34 120.3 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0(6) . . ?
C32 C31 H31 120.0 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
F4 C4 C5 120.7(6) . . ?
F4 C4 C3 119.9(6) . . ?
C5 C4 C3 119.5(6) . . ?
N4 C42 H42A 109.5 . . ?
N4 C42 H42B 109.5 . . ?
N4 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C31 C32 H32 119.3 . . ?
C31 C32 C33 121.4(6) . . ?
C33 C32 H32 119.3 . . ?
C34 C33 H33 120.3 . . ?
C32 C33 C34 119.4(6) . . ?
C32 C33 H33 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
F5 C5 C4 F4 -0.8(9) . . . . ?
F5 C5 C4 C3 179.5(5) . . . . ?
F9 C25 C24 F8 -0.9(8) . . . . ?
F9 C25 C24 C23 179.3(5) . . . . ?
F9 C25 C26 F10 1.3(8) . . . . ?
F9 C25 C26 C27 -178.6(5) . . . . ?
F2 C2 C1 F1 -1.7(8) . . . . ?
F2 C2 C1 C6 178.1(5) . . . . ?
F2 C2 C3 F3 -1.4(8) . . . . ?
F2 C2 C3 C4 -178.0(5) . . . . ?
F3 C3 C4 F4 1.9(9) . . . . ?
F3 C3 C4 C5 -178.5(6) . . . . ?
F7 C23 C24 F8 -1.2(8) . . . . ?
F7 C23 C24 C25 178.6(5) . . . . ?
F7 C23 C22 F6 0.7(8) . . . . ?
F7 C23 C22 C27 -178.6(5) . . . . ?
N3 C35 C36 C37 -175.5(5) . . . . ?
N3 C35 C40 C39 175.9(5) . . . . ?
N3 C29 C30 C31 -174.9(5) . . . . ?
N3 C29 C34 C33 175.1(5) . . . . ?
N4 C38 C37 C36 175.4(5) . . . . ?
N4 C38 C39 C40 -174.9(5) . . . . ?
N1 C14 C15 C16 -178.9(5) . . . . ?
N1 C14 C19 C18 178.9(5) . . . . ?
N1 C8 C13 C12 178.9(5) . . . . ?
N1 C8 C9 C10 -178.6(5) . . . . ?
N2 C17 C16 C15 178.0(5) . . . . ?
N2 C17 C18 C19 -177.9(5) . . . . ?
C14 N1 C8 C13 -94.7(6) . . . . ?
C14 N1 C8 C9 83.8(6) . . . . ?
C14 N1 C7 O1 0.4(8) . . . . ?
C14 N1 C7 C6 178.3(5) . . . . ?
C14 C19 C18 C17 -0.1(9) . . . . ?
C35 N3 C29 C30 92.3(6) . . . . ?
C35 N3 C29 C34 -82.7(7) . . . . ?
C35 N3 C28 O2 2.8(9) . . . . ?
C35 N3 C28 C27 -175.8(5) . . . . ?
C35 C36 C37 C38 -1.4(9) . . . . ?
C38 C39 C40 C35 0.6(9) . . . . ?
C6 C5 C4 F4 -178.4(6) . . . . ?
C6 C5 C4 C3 2.0(9) . . . . ?
C36 C35 C40 C39 -3.2(9) . . . . ?
C17 C16 C15 C14 0.0(9) . . . . ?
C29 N3 C35 C36 -67.3(7) . . . . ?
C29 N3 C35 C40 113.6(6) . . . . ?
C29 N3 C28 O2 178.7(6) . . . . ?
C29 N3 C28 C27 0.1(8) . . . . ?
C29 C30 C31 C32 0.9(9) . . . . ?
C29 C34 C33 C32 -1.3(10) . . . . ?
C37 C38 C39 C40 1.5(9) . . . . ?
C8 N1 C14 C15 -86.6(6) . . . . ?
C8 N1 C14 C19 93.9(6) . . . . ?
C8 N1 C7 O1 -173.5(6) . . . . ?
C8 N1 C7 C6 4.4(7) . . . . ?
C8 C13 C12 C11 -0.2(8) . . . . ?
C8 C9 C10 C11 -0.3(9) . . . . ?
C7 N1 C14 C15 99.2(6) . . . . ?
C7 N1 C14 C19 -80.2(6) . . . . ?
C7 N1 C8 C13 79.1(7) . . . . ?
C7 N1 C8 C9 -102.3(6) . . . . ?
C7 C6 C1 F1 -3.5(8) . . . . ?
C7 C6 C1 C2 176.7(5) . . . . ?
C7 C6 C5 F5 5.4(8) . . . . ?
C7 C6 C5 C4 -177.0(5) . . . . ?
C30 C29 C34 C33 0.2(9) . . . . ?
C30 C31 C32 C33 -2.0(10) . . . . ?
C2 C3 C4 F4 178.5(6) . . . . ?
C2 C3 C4 C5 -1.9(9) . . . . ?
C13 C8 C9 C10 -0.1(8) . . . . ?
C13 C12 C11 C10 -0.2(9) . . . . ?
C16 C17 C18 C19 0.8(9) . . . . ?
C15 C14 C19 C18 -0.5(9) . . . . ?
C24 C23 C22 F6 -179.3(5) . . . . ?
C24 C23 C22 C27 1.4(9) . . . . ?
C24 C25 C26 F10 180.0(5) . . . . ?
C24 C25 C26 C27 0.1(9) . . . . ?
C26 C27 C22 F6 -180.0(5) . . . . ?
C26 C27 C22 C23 -0.7(8) . . . . ?
C26 C27 C28 O2 96.3(7) . . . . ?
C26 C27 C28 N3 -85.0(7) . . . . ?
C26 C25 C24 F8 -179.5(5) . . . . ?
C26 C25 C24 C23 0.6(9) . . . . ?
C9 C8 C13 C12 0.3(8) . . . . ?
C9 C10 C11 C12 0.4(9) . . . . ?
C19 C14 C15 C16 0.6(9) . . . . ?
C22 C27 C26 F10 -179.9(5) . . . . ?
C22 C27 C26 C25 0.0(8) . . . . ?
C22 C27 C28 O2 -74.8(7) . . . . ?
C22 C27 C28 N3 103.8(6) . . . . ?
C22 C23 C24 F8 178.8(5) . . . . ?
C22 C23 C24 C25 -1.3(8) . . . . ?
C1 C6 C7 O1 -101.9(7) . . . . ?
C1 C6 C7 N1 80.1(7) . . . . ?
C1 C6 C5 F5 -179.4(5) . . . . ?
C1 C6 C5 C4 -1.8(9) . . . . ?
C1 C2 C3 F3 178.3(5) . . . . ?
C1 C2 C3 C4 1.6(9) . . . . ?
C18 C17 C16 C15 -0.7(9) . . . . ?
C41 N4 C38 C37 -105.7(6) . . . . ?
C41 N4 C38 C39 70.9(7) . . . . ?
C39 C38 C37 C36 -1.1(9) . . . . ?
C28 N3 C35 C36 108.9(6) . . . . ?
C28 N3 C35 C40 -70.3(7) . . . . ?
C28 N3 C29 C30 -83.6(7) . . . . ?
C28 N3 C29 C34 101.4(7) . . . . ?
C28 C27 C26 F10 8.8(8) . . . . ?
C28 C27 C26 C25 -171.3(5) . . . . ?
C28 C27 C22 F6 -8.3(8) . . . . ?
C28 C27 C22 C23 171.0(5) . . . . ?
C5 C6 C7 O1 73.1(8) . . . . ?
C5 C6 C7 N1 -104.9(6) . . . . ?
C5 C6 C1 F1 -178.6(5) . . . . ?
C5 C6 C1 C2 1.6(8) . . . . ?
C3 C2 C1 F1 178.7(5) . . . . ?
C3 C2 C1 C6 -1.5(8) . . . . ?
C40 C35 C36 C37 3.6(9) . . . . ?
C34 C29 C30 C31 0.0(8) . . . . ?
C21 N2 C17 C16 125.9(6) . . . . ?
C21 N2 C17 C18 -55.4(7) . . . . ?
C31 C32 C33 C34 2.2(10) . . . . ?
C20 N2 C17 C16 -107.7(6) . . . . ?
C20 N2 C17 C18 71.1(7) . . . . ?
C42 N4 C38 C37 128.4(6) . . . . ?
C42 N4 C38 C39 -55.0(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 2.406
_oxdiff_exptl_absorpt_empirical_full_min 0.520
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: iPrOH'
####################################################################### 
# 
# 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_ai518-211119-3ry13a-ca
_database_code_depnum_ccdc_archive 'CCDC 2149791'
loop_
_audit_author_name
_audit_author_address
'Ai Ito'
;Showa Pharmaceutical University
Japan
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;
_audit_creation_date             2021-11-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C21 H16 F5 N2 O'
_chemical_formula_sum            'C21 H16 Cl F5 N2 O'
_chemical_formula_weight         442.81
_chemical_melting_point          435-437
_chemical_oxdiff_formula         C21H16ClF5N2O
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'
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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.1986(3)
_cell_length_b                   9.3685(3)
_cell_length_c                   32.0246(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3959.88(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8823
_cell_measurement_temperature    93
_cell_measurement_theta_max      76.1700
_cell_measurement_theta_min      2.7770
_shelx_estimated_absorpt_T_max   0.758
_shelx_estimated_absorpt_T_min   0.548
_exptl_absorpt_coefficient_mu    2.279
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.63a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1808
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -6 5 0.0961
1 -2 20 0.0506
8 -1 4 0.0752
0 -1 20 0.0385
-2 -1 -20 0.0969
-8 0 -3 0.1501
-4 1 18 0.0873
4 5 -3 0.0380
6 -2 -12 0.0804
1 0 -20 0.0800
-1 1 -20 0.0892

_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.129
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.5521 -5.8337 4.5807 0.0245 0.9455 0.3247
0.6895 -1.8586 19.7269 0.8368 0.3462 0.4241
8.2492 -1.2232 3.7368 -0.0063 -0.2694 0.9630
0.4336 -1.1642 20.3756 0.8966 0.2658 0.3542
-2.1370 -0.8578 -19.8982 -0.9206 0.1209 -0.3714
-8.4542 0.3927 -3.0777 0.0099 0.4031 -0.9151
-4.1721 0.5060 18.0705 0.9261 0.2745 -0.2588
4.2991 5.1842 -3.1380 -0.0263 -0.9995 0.0160
6.4934 -1.5673 -12.4535 -0.7421 -0.2203 0.6330
1.4781 -0.1903 -20.4587 -0.9814 -0.1818 -0.0624
-1.3256 0.8120 -20.3441 -0.8934 -0.1651 -0.4178

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            15262
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.512
_diffrn_reflns_theta_min         2.760
_diffrn_ambient_temperature      93
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  25.00   0.50    0.06    --   48.95 -19.00  30.00   56
  2  ω    -20.00  24.00   0.50    0.06    --   48.95 -19.00-150.00   88
  3  ω     89.00 116.00   0.50    0.06    --   48.95 125.00 -30.00   54
  4  ω    135.00 175.00   0.50    0.24    --  107.74  86.00 -16.00   80
  5  ω    -69.00 -43.00   0.50    0.24    --  -97.00  57.00 -90.00   52
  6  ω    -70.00 -45.00   0.50    0.24    --  -97.00  57.00-150.00   50
  7  ω    -69.00 -37.00   0.50    0.24    --  -97.00  57.00-180.00   64
  8  ω    -62.00 -26.00   0.50    0.24    --  -97.00  57.00   0.00   72
  9  ω    -70.00 -25.00   0.50    0.24    --  -97.00  57.00 150.00   90
 10  ω    -51.00 -26.00   0.50    0.24    --  -97.00  40.00 150.00   50
 11  ω   -164.00 -99.00   0.50    0.24    --  -97.00 -40.00  -3.00  130
 12  ω   -153.00-127.00   0.50    0.24    --  -97.00-108.00 138.00   52
 13  ω   -120.00 -51.00   0.50    0.06    --  -48.95 -40.00  -3.00  138
 14  ω    -96.00 -24.00   0.50    0.24    --  -97.00 125.00-150.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0163736000
_diffrn_orient_matrix_UB_12      0.0366247000
_diffrn_orient_matrix_UB_13      0.0464442000
_diffrn_orient_matrix_UB_21      -0.0565179000
_diffrn_orient_matrix_UB_22      -0.1422279000
_diffrn_orient_matrix_UB_23      0.0061236000
_diffrn_orient_matrix_UB_31      0.1008007000
_diffrn_orient_matrix_UB_32      -0.0738293000
_diffrn_orient_matrix_UB_33      0.0110198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3448
_reflns_number_total             3865
_reflns_odcompleteness_completeness 99.98
_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 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3865
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+1.8568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0934
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C16 \\sim C19 \\sim C17 \\sim C1 \\sim C9 \\sim C7: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 1.7A
C4 \\sim C20 \\sim C14 \\sim C18 \\sim C6 \\sim C8: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 1.7A
C12 \\sim C21 \\sim C13 \\sim C2 \\sim C5 \\sim C11: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 1.7A
3. Rigid body (RIGU) restrains
 C16, C19, C17, C1, C9, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, C20, C14, C18, F1, C6, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, C21, C13, C2, C5, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 N2(H2)
4.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C11(H11), C13(H13), C7(H7), C2(H2A), C17(H17), C9(H9), C19(H19),
 C5(H5)
4.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C15(H15A,H15B,H15C)
;
_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
Cl1 Cl 0.12818(3) 0.51237(4) 0.20836(2) 0.02604(12) Uani 1 1 d . . . . .
F1 F 0.60721(8) 0.57865(10) 0.40618(3) 0.0300(2) Uani 1 1 d . . . . .
F4 F 0.62878(7) 0.22393(10) 0.53964(3) 0.0289(2) Uani 1 1 d . . . . .
F5 F 0.77669(7) 0.41961(11) 0.52601(3) 0.0311(2) Uani 1 1 d . . . . .
F3 F 0.46826(7) 0.20884(10) 0.48779(3) 0.0293(2) Uani 1 1 d . . . . .
F2 F 0.76317(8) 0.60125(11) 0.46037(3) 0.0359(3) Uani 1 1 d . . . . .
O1 O 0.38673(9) 0.49342(12) 0.41588(4) 0.0306(3) Uani 1 1 d . . . . .
N1 N 0.43368(9) 0.27686(13) 0.39084(4) 0.0180(3) Uani 1 1 d . . . . .
N2 N 0.10858(9) 0.30091(13) 0.27587(4) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.127206 0.379490 0.256180 0.023 Uiso 1 1 calc R U . . .
C1 C 0.35079(11) 0.27783(15) 0.36133(5) 0.0181(3) Uani 1 1 d . U . . .
C4 C 0.53440(11) 0.39173(15) 0.44521(5) 0.0187(3) Uani 1 1 d . U . . .
C6 C 0.62231(11) 0.31234(16) 0.50712(5) 0.0208(3) Uani 1 1 d . U . . .
C8 C 0.54180(11) 0.30436(15) 0.47982(5) 0.0195(3) Uani 1 1 d . U . . .
C10 C 0.44460(11) 0.39176(16) 0.41594(5) 0.0207(3) Uani 1 1 d . . . . .
C12 C 0.50691(11) 0.16259(15) 0.38778(5) 0.0187(3) Uani 1 1 d . U . . .
C14 C 0.69117(12) 0.50255(16) 0.46652(5) 0.0233(3) Uani 1 1 d . U . . .
C16 C 0.19169(11) 0.29046(15) 0.30632(5) 0.0186(3) Uani 1 1 d . U . . .
C18 C 0.69746(11) 0.41192(16) 0.50020(5) 0.0216(3) Uani 1 1 d . U . . .
C20 C 0.61071(12) 0.49166(15) 0.43928(5) 0.0212(3) Uani 1 1 d . U . . .
C21 C 0.59619(11) 0.18450(17) 0.36581(5) 0.0223(3) Uani 1 1 d . U . . .
H21 H 0.610304 0.274737 0.353589 0.027 Uiso 1 1 calc R U . . .
C11 C 0.48509(12) 0.03158(16) 0.40576(5) 0.0244(3) Uani 1 1 d . U . . .
H11 H 0.423507 0.017882 0.420582 0.029 Uiso 1 1 calc R U . . .
C3 C 0.09904(12) 0.16873(16) 0.25016(5) 0.0242(3) Uani 1 1 d . . . . .
H3A H 0.165224 0.144231 0.238278 0.036 Uiso 1 1 calc R U . . .
H3B H 0.050421 0.185104 0.227528 0.036 Uiso 1 1 calc R U . . .
H3C H 0.075217 0.090065 0.267774 0.036 Uiso 1 1 calc R U . . .
C13 C 0.66492(12) 0.07215(19) 0.36192(5) 0.0284(4) Uani 1 1 d . U . . .
H13 H 0.726321 0.085558 0.346945 0.034 Uiso 1 1 calc R U . . .
C7 C 0.28380(11) 0.34859(18) 0.29507(5) 0.0265(4) Uani 1 1 d . U . . .
H7 H 0.292209 0.392003 0.268484 0.032 Uiso 1 1 calc R U . . .
C15 C 0.00957(11) 0.34236(17) 0.29513(5) 0.0246(3) Uani 1 1 d . . . . .
H15A H -0.015606 0.263614 0.312392 0.037 Uiso 1 1 calc R U . . .
H15B H -0.039633 0.363317 0.273042 0.037 Uiso 1 1 calc R U . . .
H15C H 0.019098 0.427287 0.312553 0.037 Uiso 1 1 calc R U . . .
C2 C 0.64369(13) -0.05867(19) 0.37986(6) 0.0302(4) Uani 1 1 d . U . . .
H2A H 0.690621 -0.134984 0.377111 0.036 Uiso 1 1 calc R U . . .
C17 C 0.25923(12) 0.21645(19) 0.37191(5) 0.0270(3) Uani 1 1 d . U . . .
H17 H 0.251323 0.170173 0.398106 0.032 Uiso 1 1 calc R U . . .
C9 C 0.36425(11) 0.34286(19) 0.32313(5) 0.0267(4) Uani 1 1 d . U . . .
H9 H 0.427901 0.383449 0.316010 0.032 Uiso 1 1 calc R U . . .
C19 C 0.17877(12) 0.22275(19) 0.34405(5) 0.0281(4) Uani 1 1 d . U . . .
H19 H 0.115453 0.180734 0.350967 0.034 Uiso 1 1 calc R U . . .
C5 C 0.55409(13) -0.07934(17) 0.40190(6) 0.0304(4) Uani 1 1 d . U . . .
H5 H 0.540146 -0.169335 0.414304 0.036 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
F1 C20 1.3376(18) . ?
F4 C6 1.3333(18) . ?
F5 C18 1.3348(17) . ?
F3 C8 1.3446(17) . ?
F2 C14 1.3405(18) . ?
O1 C10 1.2208(19) . ?
N1 C1 1.4457(18) . ?
N1 C10 1.351(2) . ?
N1 C12 1.4456(18) . ?
N2 H2 1.0000 . ?
N2 C16 1.4710(18) . ?
N2 C3 1.4925(19) . ?
N2 C15 1.4962(19) . ?
C1 C17 1.381(2) . ?
C1 C9 1.378(2) . ?
C4 C8 1.381(2) . ?
C4 C10 1.511(2) . ?
C4 C20 1.388(2) . ?
C6 C8 1.378(2) . ?
C6 C18 1.380(2) . ?
C12 C21 1.388(2) . ?
C12 C11 1.386(2) . ?
C14 C18 1.375(2) . ?
C14 C20 1.378(2) . ?
C16 C7 1.380(2) . ?
C16 C19 1.375(2) . ?
C21 H21 0.9500 . ?
C21 C13 1.395(2) . ?
C11 H11 0.9500 . ?
C11 C5 1.387(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C2 1.382(3) . ?
C7 H7 0.9500 . ?
C7 C9 1.392(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C2 H2A 0.9500 . ?
C2 C5 1.391(3) . ?
C17 H17 0.9500 . ?
C17 C19 1.388(2) . ?
C9 H9 0.9500 . ?
C19 H19 0.9500 . ?
C5 H5 0.9500 . ?

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
C10 N1 C1 117.68(12) . . ?
C10 N1 C12 123.99(12) . . ?
C12 N1 C1 117.79(12) . . ?
C16 N2 H2 106.5 . . ?
C16 N2 C3 111.92(11) . . ?
C16 N2 C15 113.29(12) . . ?
C3 N2 H2 106.5 . . ?
C3 N2 C15 111.66(12) . . ?
C15 N2 H2 106.5 . . ?
C17 C1 N1 119.95(13) . . ?
C9 C1 N1 119.04(13) . . ?
C9 C1 C17 120.99(14) . . ?
C8 C4 C10 123.60(13) . . ?
C8 C4 C20 117.28(13) . . ?
C20 C4 C10 118.94(13) . . ?
F4 C6 C8 120.75(13) . . ?
F4 C6 C18 119.97(13) . . ?
C8 C6 C18 119.28(14) . . ?
F3 C8 C4 119.72(13) . . ?
F3 C8 C6 118.17(13) . . ?
C6 C8 C4 122.10(13) . . ?
O1 C10 N1 123.63(14) . . ?
O1 C10 C4 119.46(13) . . ?
N1 C10 C4 116.91(12) . . ?
C21 C12 N1 119.51(13) . . ?
C11 C12 N1 119.26(13) . . ?
C11 C12 C21 121.20(14) . . ?
F2 C14 C18 119.89(14) . . ?
F2 C14 C20 120.28(15) . . ?
C18 C14 C20 119.83(14) . . ?
C7 C16 N2 117.24(13) . . ?
C19 C16 N2 121.37(13) . . ?
C19 C16 C7 121.38(14) . . ?
F5 C18 C6 120.02(14) . . ?
F5 C18 C14 119.97(14) . . ?
C14 C18 C6 120.01(14) . . ?
F1 C20 C4 119.63(14) . . ?
F1 C20 C14 118.89(14) . . ?
C14 C20 C4 121.48(14) . . ?
C12 C21 H21 120.5 . . ?
C12 C21 C13 119.07(15) . . ?
C13 C21 H21 120.5 . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C5 119.34(15) . . ?
C5 C11 H11 120.3 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C21 C13 H13 120.0 . . ?
C2 C13 C21 120.00(15) . . ?
C2 C13 H13 120.0 . . ?
C16 C7 H7 120.4 . . ?
C16 C7 C9 119.22(15) . . ?
C9 C7 H7 120.4 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C2 H2A 119.8 . . ?
C13 C2 C5 120.45(15) . . ?
C5 C2 H2A 119.8 . . ?
C1 C17 H17 120.2 . . ?
C1 C17 C19 119.60(14) . . ?
C19 C17 H17 120.2 . . ?
C1 C9 C7 119.46(14) . . ?
C1 C9 H9 120.3 . . ?
C7 C9 H9 120.3 . . ?
C16 C19 C17 119.31(14) . . ?
C16 C19 H19 120.3 . . ?
C17 C19 H19 120.3 . . ?
C11 C5 C2 119.94(16) . . ?
C11 C5 H5 120.0 . . ?
C2 C5 H5 120.0 . . ?

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
F4 C6 C8 F3 2.5(2) . . . . ?
F4 C6 C8 C4 -178.16(13) . . . . ?
F4 C6 C18 F5 0.1(2) . . . . ?
F4 C6 C18 C14 179.59(13) . . . . ?
F2 C14 C18 F5 -1.9(2) . . . . ?
F2 C14 C18 C6 178.57(13) . . . . ?
F2 C14 C20 F1 1.6(2) . . . . ?
F2 C14 C20 C4 -179.12(14) . . . . ?
N1 C1 C17 C19 177.48(15) . . . . ?
N1 C1 C9 C7 -177.83(15) . . . . ?
N1 C12 C21 C13 -178.00(13) . . . . ?
N1 C12 C11 C5 178.30(14) . . . . ?
N2 C16 C7 C9 179.14(15) . . . . ?
N2 C16 C19 C17 -179.54(15) . . . . ?
C1 N1 C10 O1 2.4(2) . . . . ?
C1 N1 C10 C4 -177.33(12) . . . . ?
C1 N1 C12 C21 96.01(16) . . . . ?
C1 N1 C12 C11 -81.96(18) . . . . ?
C1 C17 C19 C16 -0.1(3) . . . . ?
C8 C4 C10 O1 108.96(18) . . . . ?
C8 C4 C10 N1 -71.33(19) . . . . ?
C8 C4 C20 F1 179.85(13) . . . . ?
C8 C4 C20 C14 0.6(2) . . . . ?
C8 C6 C18 F5 -179.01(13) . . . . ?
C8 C6 C18 C14 0.5(2) . . . . ?
C10 N1 C1 C17 -93.53(18) . . . . ?
C10 N1 C1 C9 85.30(18) . . . . ?
C10 N1 C12 C21 -75.38(19) . . . . ?
C10 N1 C12 C11 106.65(17) . . . . ?
C10 C4 C8 F3 2.9(2) . . . . ?
C10 C4 C8 C6 -176.48(14) . . . . ?
C10 C4 C20 F1 -4.9(2) . . . . ?
C10 C4 C20 C14 175.86(14) . . . . ?
C12 N1 C1 C17 94.53(17) . . . . ?
C12 N1 C1 C9 -86.64(17) . . . . ?
C12 N1 C10 O1 173.76(15) . . . . ?
C12 N1 C10 C4 -5.9(2) . . . . ?
C12 C21 C13 C2 -0.1(2) . . . . ?
C12 C11 C5 C2 -0.5(3) . . . . ?
C16 C7 C9 C1 0.8(3) . . . . ?
C18 C6 C8 F3 -178.40(13) . . . . ?
C18 C6 C8 C4 1.0(2) . . . . ?
C18 C14 C20 F1 -178.48(13) . . . . ?
C18 C14 C20 C4 0.7(2) . . . . ?
C20 C4 C8 F3 177.86(13) . . . . ?
C20 C4 C8 C6 -1.5(2) . . . . ?
C20 C4 C10 O1 -66.0(2) . . . . ?
C20 C4 C10 N1 113.74(16) . . . . ?
C20 C14 C18 F5 178.18(13) . . . . ?
C20 C14 C18 C6 -1.3(2) . . . . ?
C21 C12 C11 C5 0.4(2) . . . . ?
C21 C13 C2 C5 -0.1(3) . . . . ?
C11 C12 C21 C13 -0.1(2) . . . . ?
C3 N2 C16 C7 96.04(16) . . . . ?
C3 N2 C16 C19 -82.55(18) . . . . ?
C13 C2 C5 C11 0.4(3) . . . . ?
C7 C16 C19 C17 1.9(3) . . . . ?
C15 N2 C16 C7 -136.63(14) . . . . ?
C15 N2 C16 C19 44.79(19) . . . . ?
C17 C1 C9 C7 1.0(2) . . . . ?
C9 C1 C17 C19 -1.3(3) . . . . ?
C19 C16 C7 C9 -2.3(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 2.008
_oxdiff_exptl_absorpt_empirical_full_min 0.523
_exptl_crystal_recrystallization_method Sublimation
