# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_c1-4f-cl
_database_code_depnum_ccdc_archive 'CCDC 2116928'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2021-10-21 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;
_audit_creation_date             2020-12-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H7 Cl F4 O'
_chemical_formula_sum            'C15 H7 Cl F4 O'
_chemical_formula_weight         314.66
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H7ClF4O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.2618(3)
_cell_length_b                   7.4426(3)
_cell_length_c                   29.3159(10)
_cell_angle_alpha                90.733(3)
_cell_angle_beta                 92.011(3)
_cell_angle_gamma                97.051(4)
_cell_volume                     1354.87(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7188
_cell_measurement_temperature    299
_cell_measurement_theta_max      29.6470
_cell_measurement_theta_min      2.7000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
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    1.543
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -10 -1 0.2037
9 -1 -4 0.1912
0 10 -1 0.1187
-9 -1 4 0.1666
-2 -10 2 0.1700
0 0 41 0.0390
-8 5 2 0.2387
0 0 -41 0.0420
-2 -8 -22 0.1292
3 -9 -18 0.1719
0 -3 -40 0.0533
2 3 -39 0.0542

_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.081
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
4.3640 -9.6854 -1.1089 -0.0017 0.5965 0.8026
8.7959 -0.7673 -4.3524 -0.0008 -0.4472 0.8944
0.4539 10.3324 -1.3956 0.0015 -0.9353 -0.3539
-8.5173 -1.3986 4.4563 0.0004 0.6214 -0.7835
-1.8271 -9.9181 2.0418 -0.0013 0.9792 0.2029
0.2936 0.2374 41.1940 0.9993 0.0011 -0.0377
-8.0855 5.3550 1.8862 -0.0370 0.0006 -0.9993
-0.3158 -0.2227 -41.1887 -0.9994 -0.0011 0.0350
-1.9975 -7.9995 -21.9999 -0.5786 0.7978 0.1453
3.0055 -8.9987 -18.0002 -0.4242 0.5990 0.6669
0.0006 -3.0023 -39.9957 -0.9747 0.2259 0.1719
1.9987 2.9961 -38.9936 -0.9091 -0.4161 0.1332

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            19816
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.086
_diffrn_ambient_temperature      299
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     48.00  74.00   0.25    4.67    --    5.00  76.00-150.00  104
  2  ω     -5.00  21.00   0.25    4.67    --    5.00  76.00-150.00  104
  3  ω    -53.00  30.00   0.25    4.67    --  -11.60  76.00  30.00  332
  4  ω    -53.00  24.00   0.25    4.67    --  -11.60  76.00 120.00  308
  5  ω     52.00  77.00   0.25    4.67    --  -11.60  38.00   0.00  100
  6  ω     11.00  78.00   0.25    4.67    --  -11.60  57.00 -90.00  268
  7  ω    -47.00  20.00   0.25    4.67    --  -11.60  57.00 -60.00  268
  8  ω    -53.00  78.00   0.25    4.67    --  -11.60  76.00-180.00  524
  9  ω     53.00  78.00   0.25    4.67    --  -11.60  76.00  30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0121154000
_diffrn_orient_matrix_UB_12      0.0028711000
_diffrn_orient_matrix_UB_13      0.0241552000
_diffrn_orient_matrix_UB_21      -0.0580378000
_diffrn_orient_matrix_UB_22      -0.0878423000
_diffrn_orient_matrix_UB_23      0.0009455000
_diffrn_orient_matrix_UB_31      0.0976211000
_diffrn_orient_matrix_UB_32      -0.0387262000
_diffrn_orient_matrix_UB_33      -0.0013889000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3901
_reflns_number_total             6184
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_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         0.478
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0707
_refine_ls_restrained_S_all      1.060
_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)+(0.1420P)²+0.1516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2179
_refine_ls_wR_factor_ref         0.2402
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00L(H00L), C00N(H00N), C00V(H00V), C00X(H00X),
 C00Y(H00Y), C012(H012)
2.b Idealised Me refined as rotating group:
 C010(H01D,H01E,H01F), C016(H01A,H01B,H01C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.75472(16) 0.38111(12) 0.70727(3) 0.0906(3) Uani 1 1 d . . . . .
Cl02 Cl 1.2288(2) 0.22171(18) 0.76987(3) 0.1216(5) Uani 1 1 d . . . . .
F003 F 0.5736(3) 0.1491(2) 0.54682(6) 0.0733(4) Uani 1 1 d . . . . .
F004 F 1.2722(2) 0.4579(2) 0.58076(6) 0.0775(5) Uani 1 1 d . . . . .
F005 F 0.4791(2) 0.1986(2) 0.63478(6) 0.0773(5) Uani 1 1 d . . . . .
F006 F 1.1713(3) 0.5031(2) 0.66740(6) 0.0831(5) Uani 1 1 d . . . . .
F007 F 1.7547(3) 0.3880(3) 0.90086(7) 0.0982(6) Uani 1 1 d . . . . .
F008 F 1.0660(3) 0.1096(3) 0.93411(8) 0.1045(7) Uani 1 1 d . . . . .
O009 O 1.1938(4) 0.0898(3) 0.29725(7) 0.0843(6) Uani 1 1 d . . . . .
F00A F 0.9572(3) 0.0938(3) 0.84525(8) 0.1129(7) Uani 1 1 d . . . . .
F00B F 1.6456(4) 0.3750(4) 0.81242(7) 0.1159(8) Uani 1 1 d . . . . .
O10 O 1.7079(4) 0.2498(4) 1.19374(7) 0.0968(7) Uani 1 1 d . . . . .
C00D C 1.0820(4) 0.2004(3) 0.43192(8) 0.0538(6) Uani 1 1 d . . . . .
C00E C 0.9304(4) 0.3011(3) 0.56164(8) 0.0538(6) Uani 1 1 d . . . . .
C00F C 0.6765(4) 0.2639(3) 0.62133(9) 0.0573(6) Uani 1 1 d . . . . .
C00G C 0.7276(4) 0.2386(3) 0.57669(8) 0.0554(6) Uani 1 1 d . . . . .
C00H C 0.9235(4) 0.1128(3) 0.40236(9) 0.0597(6) Uani 1 1 d . . . . .
H00H H 0.786865 0.076771 0.412929 0.072 Uiso 1 1 calc R U . . .
C00I C 1.2855(4) 0.2504(3) 0.41567(9) 0.0604(6) Uani 1 1 d . . . . .
H00I H 1.393456 0.307206 0.435349 0.073 Uiso 1 1 calc R U . . .
C00J C 1.1706(4) 0.1314(3) 0.34164(9) 0.0598(6) Uani 1 1 d . . . . .
C00K C 1.0226(4) 0.4161(3) 0.63792(9) 0.0580(6) Uani 1 1 d . . . . .
C00L C 1.3308(4) 0.2177(3) 0.37085(9) 0.0615(6) Uani 1 1 d . . . . .
H00L H 1.467747 0.253146 0.360328 0.074 Uiso 1 1 calc R U . . .
C00M C 1.0738(4) 0.3926(3) 0.59357(9) 0.0566(6) Uani 1 1 d . . . . .
C00N C 0.9662(4) 0.0790(4) 0.35787(9) 0.0634(6) Uani 1 1 d . . . . .
H00N H 0.858481 0.020792 0.338359 0.076 Uiso 1 1 calc R U . . .
C00O C 1.0336(4) 0.2386(3) 0.47826(9) 0.0605(6) Uani 1 1 d . . . . .
C00P C 0.9867(4) 0.2692(3) 0.51616(9) 0.0589(6) Uani 1 1 d . . . . .
C00Q C 0.8220(4) 0.3523(3) 0.65233(8) 0.0576(6) Uani 1 1 d . . . . .
C00R C 1.5757(5) 0.2570(4) 1.05480(9) 0.0673(7) Uani 1 1 d . . . . .
C00S C 1.4141(4) 0.2487(3) 0.92008(9) 0.0644(7) Uani 1 1 d . . . . .
C00T C 1.6751(5) 0.2572(4) 1.14736(10) 0.0698(7) Uani 1 1 d . . . . .
C00U C 1.2115(5) 0.1758(4) 0.90414(11) 0.0702(7) Uani 1 1 d . . . . .
C00V C 1.8313(5) 0.3198(4) 1.11801(10) 0.0738(8) Uani 1 1 d . . . . .
H00V H 1.969707 0.361987 1.129000 0.089 Uiso 1 1 calc R U . . .
C00W C 1.5246(5) 0.2557(4) 1.00702(11) 0.0773(8) Uani 1 1 d . . . . .
C00X C 1.7801(5) 0.3192(4) 1.07187(10) 0.0753(8) Uani 1 1 d . . . . .
H00X H 1.885720 0.361763 1.051787 0.090 Uiso 1 1 calc R U . . .
C00Y C 1.4219(5) 0.1935(4) 1.08536(10) 0.0743(8) Uani 1 1 d . . . . .
H00Y H 1.283503 0.149710 1.074614 0.089 Uiso 1 1 calc R U . . .
C00Z C 1.4741(5) 0.2547(4) 0.96717(11) 0.0755(8) Uani 1 1 d . . . . .
C010 C 1.9131(6) 0.3008(5) 1.21433(11) 0.0909(10) Uani 1 1 d . . . . .
H01D H 2.013869 0.227728 1.201900 0.136 Uiso 1 1 calc R U . . .
H01E H 1.906940 0.283305 1.246668 0.136 Uiso 1 1 calc R U . . .
H01F H 1.958508 0.425989 1.208469 0.136 Uiso 1 1 calc R U . . .
C011 C 1.5565(5) 0.3147(4) 0.88726(10) 0.0696(7) Uani 1 1 d . . . . .
C012 C 1.4710(5) 0.1945(4) 1.13122(11) 0.0779(8) Uani 1 1 d . . . . .
H012 H 1.365803 0.152562 1.151470 0.093 Uiso 1 1 calc R U . . .
C013 C 1.2974(6) 0.2324(4) 0.82651(11) 0.0782(8) Uani 1 1 d . . . . .
C014 C 1.1551(5) 0.1663(4) 0.85864(12) 0.0771(8) Uani 1 1 d . . . . .
C015 C 1.4995(5) 0.3074(4) 0.84197(10) 0.0774(8) Uani 1 1 d . . . . .
C016 C 1.4007(6) 0.1342(6) 0.27816(12) 0.1024(12) Uani 1 1 d . . . . .
H01A H 1.391901 0.102567 0.246238 0.154 Uiso 1 1 calc R U . . .
H01B H 1.503403 0.067997 0.293486 0.154 Uiso 1 1 calc R U . . .
H01C H 1.445354 0.261713 0.281953 0.154 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
Cl01 C00Q 1.697(3) . ?
Cl02 C013 1.699(3) . ?
F003 C00G 1.381(3) . ?
F004 C00M 1.345(3) . ?
F005 C00F 1.346(3) . ?
F006 C00K 1.347(3) . ?
F007 C011 1.338(3) . ?
F008 C00U 1.342(3) . ?
O009 C00J 1.351(3) . ?
O009 C016 1.432(4) . ?
F00A C014 1.333(4) . ?
F00B C015 1.339(4) . ?
O10 C00T 1.371(4) . ?
O10 C010 1.407(4) . ?
C00D C00H 1.388(4) . ?
C00D C00I 1.385(4) . ?
C00D C00O 1.435(3) . ?
C00E C00G 1.387(4) . ?
C00E C00M 1.386(4) . ?
C00E C00P 1.415(3) . ?
C00F C00G 1.374(3) . ?
C00F C00Q 1.367(4) . ?
C00H H00H 0.9300 . ?
C00H C00N 1.367(4) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.379(3) . ?
C00J C00L 1.385(4) . ?
C00J C00N 1.393(4) . ?
C00K C00M 1.364(4) . ?
C00K C00Q 1.370(4) . ?
C00L H00L 0.9300 . ?
C00N H00N 0.9300 . ?
C00O C00P 1.186(4) . ?
C00R C00W 1.425(4) . ?
C00R C00X 1.381(4) . ?
C00R C00Y 1.383(4) . ?
C00S C00U 1.380(4) . ?
C00S C00Z 1.416(4) . ?
C00S C011 1.388(4) . ?
C00T C00V 1.368(4) . ?
C00T C012 1.371(4) . ?
C00U C014 1.366(4) . ?
C00V H00V 0.9300 . ?
C00V C00X 1.379(4) . ?
C00W C00Z 1.199(4) . ?
C00X H00X 0.9300 . ?
C00Y H00Y 0.9300 . ?
C00Y C012 1.369(4) . ?
C010 H01D 0.9600 . ?
C010 H01E 0.9600 . ?
C010 H01F 0.9600 . ?
C011 C015 1.361(4) . ?
C012 H012 0.9300 . ?
C013 C014 1.374(5) . ?
C013 C015 1.378(5) . ?
C016 H01A 0.9600 . ?
C016 H01B 0.9600 . ?
C016 H01C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00J O009 C016 118.5(3) . . ?
C00T O10 C010 120.9(3) . . ?
C00H C00D C00O 120.1(2) . . ?
C00I C00D C00H 118.7(2) . . ?
C00I C00D C00O 121.2(2) . . ?
C00G C00E C00P 121.1(2) . . ?
C00M C00E C00G 116.5(2) . . ?
C00M C00E C00P 122.4(2) . . ?
F005 C00F C00G 119.0(2) . . ?
F005 C00F C00Q 119.5(2) . . ?
C00Q C00F C00G 121.5(2) . . ?
F003 C00G C00E 120.2(2) . . ?
C00F C00G F003 119.0(2) . . ?
C00F C00G C00E 120.9(2) . . ?
C00D C00H H00H 119.6 . . ?
C00N C00H C00D 120.7(2) . . ?
C00N C00H H00H 119.6 . . ?
C00D C00I H00I 119.4 . . ?
C00L C00I C00D 121.2(2) . . ?
C00L C00I H00I 119.4 . . ?
O009 C00J C00L 125.5(2) . . ?
O009 C00J C00N 114.9(2) . . ?
C00L C00J C00N 119.7(2) . . ?
F006 C00K C00M 119.3(2) . . ?
F006 C00K C00Q 120.3(2) . . ?
C00M C00K C00Q 120.4(2) . . ?
C00I C00L C00J 119.4(2) . . ?
C00I C00L H00L 120.3 . . ?
C00J C00L H00L 120.3 . . ?
F004 C00M C00E 119.1(2) . . ?
F004 C00M C00K 118.5(2) . . ?
C00K C00M C00E 122.4(2) . . ?
C00H C00N C00J 120.2(2) . . ?
C00H C00N H00N 119.9 . . ?
C00J C00N H00N 119.9 . . ?
C00P C00O C00D 177.9(3) . . ?
C00O C00P C00E 178.6(3) . . ?
C00F C00Q Cl01 120.5(2) . . ?
C00F C00Q C00K 118.4(2) . . ?
C00K C00Q Cl01 121.1(2) . . ?
C00X C00R C00W 121.2(3) . . ?
C00X C00R C00Y 118.1(3) . . ?
C00Y C00R C00W 120.7(3) . . ?
C00U C00S C00Z 122.0(3) . . ?
C00U C00S C011 116.1(3) . . ?
C011 C00S C00Z 121.8(3) . . ?
O10 C00T C012 115.3(3) . . ?
C00V C00T O10 124.0(3) . . ?
C00V C00T C012 120.6(3) . . ?
F008 C00U C00S 119.1(3) . . ?
F008 C00U C014 118.8(3) . . ?
C014 C00U C00S 122.0(3) . . ?
C00T C00V H00V 120.5 . . ?
C00T C00V C00X 118.9(3) . . ?
C00X C00V H00V 120.5 . . ?
C00Z C00W C00R 177.7(4) . . ?
C00R C00X H00X 119.2 . . ?
C00V C00X C00R 121.5(3) . . ?
C00V C00X H00X 119.2 . . ?
C00R C00Y H00Y 119.6 . . ?
C012 C00Y C00R 120.7(3) . . ?
C012 C00Y H00Y 119.6 . . ?
C00W C00Z C00S 178.5(3) . . ?
O10 C010 H01D 109.5 . . ?
O10 C010 H01E 109.5 . . ?
O10 C010 H01F 109.5 . . ?
H01D C010 H01E 109.5 . . ?
H01D C010 H01F 109.5 . . ?
H01E C010 H01F 109.5 . . ?
F007 C011 C00S 118.6(3) . . ?
F007 C011 C015 119.5(3) . . ?
C015 C011 C00S 121.8(3) . . ?
C00T C012 H012 120.0 . . ?
C00Y C012 C00T 120.1(3) . . ?
C00Y C012 H012 120.0 . . ?
C014 C013 Cl02 121.6(3) . . ?
C014 C013 C015 117.3(3) . . ?
C015 C013 Cl02 121.0(3) . . ?
F00A C014 C00U 119.4(3) . . ?
F00A C014 C013 119.4(3) . . ?
C00U C014 C013 121.2(3) . . ?
F00B C015 C011 118.3(3) . . ?
F00B C015 C013 120.3(3) . . ?
C011 C015 C013 121.4(3) . . ?
O009 C016 H01A 109.5 . . ?
O009 C016 H01B 109.5 . . ?
O009 C016 H01C 109.5 . . ?
H01A C016 H01B 109.5 . . ?
H01A C016 H01C 109.5 . . ?
H01B C016 H01C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl02 C013 C014 F00A -0.8(4) . . . . ?
Cl02 C013 C014 C00U -179.8(2) . . . . ?
Cl02 C013 C015 F00B 0.6(4) . . . . ?
Cl02 C013 C015 C011 -179.3(2) . . . . ?
F005 C00F C00G F003 1.0(3) . . . . ?
F005 C00F C00G C00E -178.9(2) . . . . ?
F005 C00F C00Q Cl01 -0.5(3) . . . . ?
F005 C00F C00Q C00K 179.4(2) . . . . ?
F006 C00K C00M F004 -0.1(3) . . . . ?
F006 C00K C00M C00E 178.6(2) . . . . ?
F006 C00K C00Q Cl01 0.2(3) . . . . ?
F006 C00K C00Q C00F -179.7(2) . . . . ?
F007 C011 C015 F00B -0.2(5) . . . . ?
F007 C011 C015 C013 179.7(3) . . . . ?
F008 C00U C014 F00A 0.8(5) . . . . ?
F008 C00U C014 C013 179.8(3) . . . . ?
O009 C00J C00L C00I -179.4(2) . . . . ?
O009 C00J C00N C00H 179.6(2) . . . . ?
O10 C00T C00V C00X 179.4(3) . . . . ?
O10 C00T C012 C00Y -179.1(3) . . . . ?
C00D C00H C00N C00J 0.3(4) . . . . ?
C00D C00I C00L C00J -0.7(4) . . . . ?
C00G C00E C00M F004 -179.3(2) . . . . ?
C00G C00E C00M C00K 1.9(3) . . . . ?
C00G C00F C00Q Cl01 -179.81(18) . . . . ?
C00G C00F C00Q C00K 0.0(4) . . . . ?
C00H C00D C00I C00L 1.1(4) . . . . ?
C00I C00D C00H C00N -1.0(4) . . . . ?
C00L C00J C00N C00H 0.2(4) . . . . ?
C00M C00E C00G F003 178.8(2) . . . . ?
C00M C00E C00G C00F -1.4(3) . . . . ?
C00M C00K C00Q Cl01 -179.68(18) . . . . ?
C00M C00K C00Q C00F 0.5(4) . . . . ?
C00N C00J C00L C00I 0.0(4) . . . . ?
C00O C00D C00H C00N 178.6(2) . . . . ?
C00O C00D C00I C00L -178.4(2) . . . . ?
C00P C00E C00G F003 -2.4(3) . . . . ?
C00P C00E C00G C00F 177.5(2) . . . . ?
C00P C00E C00M F004 1.8(3) . . . . ?
C00P C00E C00M C00K -177.0(2) . . . . ?
C00Q C00F C00G F003 -179.7(2) . . . . ?
C00Q C00F C00G C00E 0.4(4) . . . . ?
C00Q C00K C00M F004 179.7(2) . . . . ?
C00Q C00K C00M C00E -1.5(4) . . . . ?
C00R C00Y C012 C00T -0.6(5) . . . . ?
C00S C00U C014 F00A 179.7(3) . . . . ?
C00S C00U C014 C013 -1.3(5) . . . . ?
C00S C011 C015 F00B 179.6(3) . . . . ?
C00S C011 C015 C013 -0.5(5) . . . . ?
C00T C00V C00X C00R -0.1(5) . . . . ?
C00U C00S C011 F007 179.5(3) . . . . ?
C00U C00S C011 C015 -0.2(4) . . . . ?
C00V C00T C012 C00Y 0.2(5) . . . . ?
C00W C00R C00X C00V -179.5(3) . . . . ?
C00W C00R C00Y C012 179.9(3) . . . . ?
C00X C00R C00Y C012 0.7(5) . . . . ?
C00Y C00R C00X C00V -0.4(5) . . . . ?
C00Z C00S C00U F008 0.4(4) . . . . ?
C00Z C00S C00U C014 -178.5(3) . . . . ?
C00Z C00S C011 F007 -0.9(4) . . . . ?
C00Z C00S C011 C015 179.4(3) . . . . ?
C010 O10 C00T C00V -2.7(5) . . . . ?
C010 O10 C00T C012 176.5(3) . . . . ?
C011 C00S C00U F008 -180.0(3) . . . . ?
C011 C00S C00U C014 1.1(4) . . . . ?
C012 C00T C00V C00X 0.2(5) . . . . ?
C014 C013 C015 F00B -179.7(3) . . . . ?
C014 C013 C015 C011 0.4(5) . . . . ?
C015 C013 C014 F00A 179.5(3) . . . . ?
C015 C013 C014 C00U 0.5(5) . . . . ?
C016 O009 C00J C00L 1.2(4) . . . . ?
C016 O009 C00J C00N -178.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.614
_oxdiff_exptl_absorpt_empirical_full_min 0.430
####################################################################### 
# 
# 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_c1_4f_i
_database_code_depnum_ccdc_archive 'CCDC 2116930'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2021-10-21 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;
_audit_creation_date             2020-10-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H7 F4 I O'
_chemical_formula_sum            'C15 H7 F4 I O'
_chemical_formula_weight         406.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H7F4IO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   16.2038(6)
_cell_length_b                   6.1025(2)
_cell_length_c                   28.4996(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2818.15(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8350
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.6460
_cell_measurement_theta_min      2.4700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.312
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
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    1.914
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -9 -2 0.2646
-23 0 1 0.3131
-13 7 2 0.2942
-1 9 2 0.2737
23 1 -1 0.2940
-1 0 -40 0.0181
1 0 40 0.0767
-4 0 40 0.1187
-4 1 39 0.1231
-15 0 31 0.2296
15 -1 -31 0.2043
-10 1 -36 0.1395

_exptl_crystal_size_max          0.619
_exptl_crystal_size_mid          0.538
_exptl_crystal_size_min          0.096
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
1.2483 -8.5796 -2.0859 -0.0340 -0.1610 0.9864
-22.8273 -0.1961 0.9798 0.2052 0.9701 0.1295
-13.2818 6.9725 2.2467 0.1382 0.6535 -0.7442
-1.2483 8.5796 2.0859 0.0340 0.1610 -0.9864
22.7849 0.5796 -0.8872 -0.2038 -0.9635 -0.1736
-0.7718 -0.2546 -40.1365 -0.9750 0.2062 0.0824
0.7598 0.2130 40.1428 0.9754 -0.2063 -0.0775
-4.0000 -0.0000 40.0005 1.0102 -0.0049 -0.0302
-4.0000 1.0000 39.0005 0.9826 0.0132 -0.1444
-15.0000 -0.0000 31.0003 0.8771 0.5056 0.0329
15.0000 -1.0000 -31.0003 -0.8739 -0.5192 0.0825
-10.0000 1.0000 -36.0005 -0.8048 0.6001 -0.0238

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            17132
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.514
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  19.00   0.25    0.60    --    5.00   9.00-168.00  100
  2  ω    -23.00   3.00   0.25    0.60    --  -11.80   9.00-168.00  104
  3  ω    -28.00  -3.00   0.25    0.60    --    5.00  57.00 -90.00  100
  4  ω    -47.00  77.00   0.25    0.60    --  -11.80  57.00 -60.00  496
  5  ω    -47.00  -6.00   0.25    0.60    --  -11.80  57.00-120.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0079105000
_diffrn_orient_matrix_UB_12      -0.0031327000
_diffrn_orient_matrix_UB_13      0.0244648000
_diffrn_orient_matrix_UB_21      -0.0428042000
_diffrn_orient_matrix_UB_22      0.0136057000
_diffrn_orient_matrix_UB_23      -0.0044017000
_diffrn_orient_matrix_UB_31      -0.0047341000
_diffrn_orient_matrix_UB_32      -0.1153563000
_diffrn_orient_matrix_UB_33      -0.0012295000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2502
_reflns_number_total             3217
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_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         0.761
_refine_diff_density_min         -0.851
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.100
_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)+(0.0467P)²+1.2443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0983
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C6(H6), C3(H3)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
I1 I 0.40073(2) 1.13169(4) 0.23311(2) 0.06501(14) Uani 1 1 d . . . . .
F2 F 0.46874(14) 1.2517(3) 0.33547(8) 0.0769(6) Uani 1 1 d . . . . .
F3 F 0.31673(16) 0.6862(4) 0.26426(7) 0.0796(6) Uani 1 1 d . . . . .
F1 F 0.45516(14) 1.0508(4) 0.41782(7) 0.0786(6) Uani 1 1 d . . . . .
F4 F 0.30528(14) 0.4818(3) 0.34640(8) 0.0788(6) Uani 1 1 d . . . . .
O1 O 0.37406(17) 0.1280(3) 0.63784(8) 0.0627(6) Uani 1 1 d . . . . .
C2 C 0.3709(2) 0.2211(5) 0.59408(10) 0.0499(6) Uani 1 1 d . . . . .
C13 C 0.39356(17) 0.9756(5) 0.29756(11) 0.0497(7) Uani 1 1 d . . . . .
C14 C 0.35249(18) 0.7770(5) 0.30185(10) 0.0517(7) Uani 1 1 d . . . . .
C10 C 0.37957(18) 0.7592(5) 0.38472(11) 0.0510(7) Uani 1 1 d . . . . .
C5 C 0.37155(19) 0.4388(5) 0.50854(11) 0.0532(7) Uani 1 1 d . . . . .
C15 C 0.34633(19) 0.6730(5) 0.34415(12) 0.0535(7) Uani 1 1 d . . . . .
C11 C 0.4208(2) 0.9591(5) 0.38003(11) 0.0548(7) Uani 1 1 d . . . . .
C7 C 0.3290(2) 0.1326(5) 0.55643(11) 0.0564(8) Uani 1 1 d . . . . .
H7 H 0.300284 0.001574 0.559644 0.068 Uiso 1 1 calc R U . . .
C12 C 0.4273(2) 1.0621(5) 0.33764(11) 0.0537(7) Uani 1 1 d . . . . .
C4 C 0.41336(19) 0.5233(5) 0.54684(12) 0.0575(8) Uani 1 1 d . . . . .
H4 H 0.441798 0.654914 0.543852 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3303(2) 0.2406(5) 0.51410(11) 0.0589(8) Uani 1 1 d . . . . .
H6 H 0.302975 0.179576 0.488560 0.071 Uiso 1 1 calc R U . . .
C3 C 0.4135(2) 0.4161(6) 0.58907(12) 0.0571(8) Uani 1 1 d . . . . .
H3 H 0.442305 0.474441 0.614386 0.069 Uiso 1 1 calc R U . . .
C9 C 0.3739(2) 0.6483(5) 0.42843(13) 0.0576(8) Uani 1 1 d . . . . .
C8 C 0.3717(2) 0.5507(6) 0.46462(12) 0.0588(7) Uani 1 1 d . . . . .
C1 C 0.3260(3) -0.0630(6) 0.64615(13) 0.0746(10) Uani 1 1 d . . . . .
H1A H 0.342380 -0.176425 0.624740 0.112 Uiso 1 1 calc R U . . .
H1B H 0.268662 -0.029683 0.641526 0.112 Uiso 1 1 calc R U . . .
H1C H 0.334458 -0.112000 0.677798 0.112 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
I1 C13 2.072(3) . ?
F2 C12 1.339(4) . ?
F3 C14 1.338(3) . ?
F1 C11 1.336(3) . ?
F4 C15 1.345(3) . ?
O1 C2 1.371(4) . ?
O1 C1 1.422(4) . ?
C2 C7 1.380(4) . ?
C2 C3 1.383(4) . ?
C13 C14 1.388(4) . ?
C13 C12 1.372(4) . ?
C14 C15 1.366(4) . ?
C10 C15 1.380(4) . ?
C10 C11 1.397(5) . ?
C10 C9 1.421(5) . ?
C5 C4 1.384(4) . ?
C5 C6 1.391(5) . ?
C5 C8 1.426(4) . ?
C11 C12 1.366(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.375(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.370(5) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C9 C8 1.191(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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 O1 C1 118.1(3) . . ?
O1 C2 C7 124.3(3) . . ?
O1 C2 C3 115.6(3) . . ?
C7 C2 C3 120.1(3) . . ?
C14 C13 I1 120.4(2) . . ?
C12 C13 I1 122.6(2) . . ?
C12 C13 C14 117.0(3) . . ?
F3 C14 C13 119.9(3) . . ?
F3 C14 C15 118.8(3) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C10 C11 116.1(3) . . ?
C15 C10 C9 121.9(3) . . ?
C11 C10 C9 122.0(3) . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 C8 120.8(3) . . ?
C6 C5 C8 121.2(3) . . ?
F4 C15 C14 118.8(3) . . ?
F4 C15 C10 118.9(3) . . ?
C14 C15 C10 122.3(3) . . ?
F1 C11 C10 119.2(3) . . ?
F1 C11 C12 119.2(3) . . ?
C12 C11 C10 121.6(3) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 C2 119.2(3) . . ?
C6 C7 H7 120.4 . . ?
F2 C12 C13 119.6(3) . . ?
F2 C12 C11 118.5(3) . . ?
C11 C12 C13 121.9(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C8 C9 C10 177.5(4) . . ?
C9 C8 C5 177.9(4) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C13 C14 F3 -0.5(4) . . . . ?
I1 C13 C14 C15 -179.2(2) . . . . ?
I1 C13 C12 F2 -1.9(4) . . . . ?
I1 C13 C12 C11 178.8(2) . . . . ?
F3 C14 C15 F4 0.7(5) . . . . ?
F3 C14 C15 C10 -178.2(3) . . . . ?
F1 C11 C12 F2 0.5(5) . . . . ?
F1 C11 C12 C13 179.8(3) . . . . ?
O1 C2 C7 C6 -179.9(3) . . . . ?
O1 C2 C3 C4 -179.3(3) . . . . ?
C2 C7 C6 C5 -1.2(5) . . . . ?
C13 C14 C15 F4 179.5(3) . . . . ?
C13 C14 C15 C10 0.6(5) . . . . ?
C14 C13 C12 F2 179.0(3) . . . . ?
C14 C13 C12 C11 -0.3(5) . . . . ?
C10 C11 C12 F2 -179.0(3) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C5 C4 C3 C2 -0.5(5) . . . . ?
C15 C10 C11 F1 -179.3(3) . . . . ?
C15 C10 C11 C12 0.1(5) . . . . ?
C11 C10 C15 F4 -179.4(3) . . . . ?
C11 C10 C15 C14 -0.5(5) . . . . ?
C7 C2 C3 C4 0.8(5) . . . . ?
C12 C13 C14 F3 178.6(3) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C4 C5 C6 C7 1.5(5) . . . . ?
C6 C5 C4 C3 -0.6(5) . . . . ?
C3 C2 C7 C6 0.0(5) . . . . ?
C9 C10 C15 F4 2.1(5) . . . . ?
C9 C10 C15 C14 -179.0(3) . . . . ?
C9 C10 C11 F1 -0.9(5) . . . . ?
C9 C10 C11 C12 178.6(3) . . . . ?
C8 C5 C4 C3 -179.9(3) . . . . ?
C8 C5 C6 C7 -179.3(3) . . . . ?
C1 O1 C2 C7 -5.1(5) . . . . ?
C1 O1 C2 C3 175.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.933
_oxdiff_exptl_absorpt_empirical_full_min 0.406
####################################################################### 
# 
# 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_c1_4f_br
_database_code_depnum_ccdc_archive 'CCDC 2116929'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2021-10-21 deposited with the CCDC.	2022-01-20 downloaded from the CCDC.
;
_audit_creation_date             2020-10-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H7 Br F4 O'
_chemical_formula_sum            'C15 H7 Br F4 O'
_chemical_formula_weight         359.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H7BrF4O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5810(5)
_cell_length_b                   28.9757(12)
_cell_length_c                   6.4309(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.322(7)
_cell_angle_gamma                90
_cell_volume                     1389.78(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4099
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.2090
_cell_measurement_theta_min      2.7690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.998
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
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    1.716
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 4 8 0.1792
-10 -3 0 0.3136
0 -4 -9 0.1945
3 4 8 0.1821
-11 -3 0 0.3241
11 2 -1 0.3027
-2 -12 9 0.2318
0 -41 0 0.0736
0 41 0 0.0782
0 -13 9 0.1873
0 17 8 0.1793

_exptl_crystal_size_max          0.687
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.156
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
3.2038 3.9963 7.9713 -0.4675 0.0981 0.8785
-10.4346 -2.8979 -0.2280 0.9782 -0.2069 -0.0185
-0.1012 -3.5137 -8.8676 0.1970 -0.0408 -0.9795
3.4972 4.0254 7.8445 -0.4922 0.1034 0.8643
-10.5200 -2.7706 0.1542 0.9781 -0.2069 0.0238
10.6545 2.4133 -1.1550 -0.9695 0.2051 -0.1345
-2.0966 -11.9873 8.6656 0.1116 0.3446 0.9321
-0.3919 -40.8370 0.1074 0.3075 0.9496 -0.0609
0.3594 40.8396 0.0343 -0.3071 -0.9486 0.0765
-0.0000 -13.0001 9.0000 -0.0796 0.4275 0.9646
-0.0001 17.0008 8.0000 -0.2621 -0.2901 0.9086

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11352
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.731
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  49.00   0.50    4.19    --    5.00  57.00 150.00  152
  2  ω    -52.00  21.00   0.50    4.19    --  -11.60  76.00-150.00  146
  3  ω     25.00  57.00   0.50    4.19    --  -11.60  76.00-150.00   64
  4  ω    -44.00  76.00   0.50    4.19    --  -11.60  57.00 -60.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0914807000
_diffrn_orient_matrix_UB_12      -0.0066998000
_diffrn_orient_matrix_UB_13      -0.0185208000
_diffrn_orient_matrix_UB_21      0.0260438000
_diffrn_orient_matrix_UB_22      -0.0234678000
_diffrn_orient_matrix_UB_23      0.0136068000
_diffrn_orient_matrix_UB_31      -0.0011262000
_diffrn_orient_matrix_UB_32      0.0017906000
_diffrn_orient_matrix_UB_33      0.1097662000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1870
_reflns_number_total             3172
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_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         0.435
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.009
_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)+(0.0400P)²+0.7382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C6(H6), C4(H4)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
Br1 Br 0.59548(6) 0.71379(2) 0.80298(7) 0.0892(2) Uani 1 1 d . . . . .
F3 F 0.8402(3) 0.54883(7) 0.9438(3) 0.0817(6) Uani 1 1 d . . . . .
F4 F 0.7868(3) 0.63516(7) 1.0607(3) 0.0813(6) Uani 1 1 d . . . . .
F1 F 0.5355(3) 0.58166(8) 0.2585(3) 0.0848(6) Uani 1 1 d . . . . .
F2 F 0.4821(3) 0.66816(7) 0.3740(3) 0.0905(6) Uani 1 1 d . . . . .
O1 O 0.9279(3) 0.30394(8) 0.2206(3) 0.0747(7) Uani 1 1 d . . . . .
C10 C 0.6920(4) 0.56248(10) 0.5964(5) 0.0538(7) Uani 1 1 d . . . . .
C5 C 0.8049(4) 0.43521(10) 0.4004(5) 0.0561(8) Uani 1 1 d . . . . .
C7 C 0.9372(4) 0.36071(11) 0.4759(5) 0.0608(8) Uani 1 1 d . . . . .
H7 H 1.000993 0.340105 0.571937 0.073 Uiso 1 1 calc R U . . .
C3 C 0.7882(4) 0.37822(11) 0.1264(5) 0.0618(8) Uani 1 1 d . . . . .
H3 H 0.750734 0.369668 -0.013984 0.074 Uiso 1 1 calc R U . . .
C15 C 0.7508(4) 0.57793(11) 0.8003(5) 0.0572(8) Uani 1 1 d . . . . .
C14 C 0.7225(4) 0.62215(11) 0.8616(5) 0.0578(8) Uani 1 1 d . . . . .
C12 C 0.5714(4) 0.63867(11) 0.5176(5) 0.0608(8) Uani 1 1 d . . . . .
C6 C 0.8995(4) 0.40384(11) 0.5411(5) 0.0596(8) Uani 1 1 d . . . . .
H6 H 0.937721 0.412321 0.681378 0.072 Uiso 1 1 calc R U . . .
C2 C 0.8811(4) 0.34744(10) 0.2683(5) 0.0562(8) Uani 1 1 d . . . . .
C8 C 0.7636(4) 0.48032(12) 0.4694(5) 0.0618(8) Uani 1 1 d . . . . .
C9 C 0.7283(4) 0.51735(11) 0.5297(5) 0.0621(8) Uani 1 1 d . . . . .
C13 C 0.6330(4) 0.65327(10) 0.7202(5) 0.0576(8) Uani 1 1 d . . . . .
C11 C 0.5988(4) 0.59444(11) 0.4577(5) 0.0587(8) Uani 1 1 d . . . . .
C4 C 0.7510(4) 0.42157(11) 0.1928(5) 0.0628(8) Uani 1 1 d . . . . .
H4 H 0.688309 0.442213 0.096070 0.075 Uiso 1 1 calc R U . . .
C1 C 0.8715(6) 0.28761(12) 0.0094(6) 0.0903(12) Uani 1 1 d . . . . .
H1A H 0.922260 0.306759 -0.086549 0.135 Uiso 1 1 calc R U . . .
H1B H 0.743098 0.288716 -0.026202 0.135 Uiso 1 1 calc R U . . .
H1C H 0.911375 0.256377 -0.000906 0.135 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
Br1 C13 1.869(3) . ?
F3 C15 1.341(3) . ?
F4 C14 1.340(3) . ?
F1 C11 1.337(3) . ?
F2 C12 1.348(3) . ?
O1 C2 1.359(4) . ?
O1 C1 1.430(4) . ?
C10 C15 1.382(4) . ?
C10 C9 1.418(4) . ?
C10 C11 1.388(4) . ?
C5 C6 1.388(4) . ?
C5 C8 1.433(4) . ?
C5 C4 1.382(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.365(4) . ?
C7 C2 1.381(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.376(4) . ?
C3 C4 1.372(4) . ?
C15 C14 1.369(4) . ?
C14 C13 1.371(4) . ?
C12 C13 1.370(4) . ?
C12 C11 1.365(4) . ?
C6 H6 0.9300 . ?
C8 C9 1.188(4) . ?
C4 H4 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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 O1 C1 118.4(3) . . ?
C15 C10 C9 122.6(3) . . ?
C15 C10 C11 115.7(3) . . ?
C11 C10 C9 121.7(3) . . ?
C6 C5 C8 120.8(3) . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 C8 121.1(3) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C2 120.4(3) . . ?
C2 C7 H7 119.8 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.7(3) . . ?
F3 C15 C10 119.1(3) . . ?
F3 C15 C14 118.5(3) . . ?
C14 C15 C10 122.4(3) . . ?
F4 C14 C15 119.3(3) . . ?
F4 C14 C13 120.0(3) . . ?
C15 C14 C13 120.6(3) . . ?
F2 C12 C13 120.0(3) . . ?
F2 C12 C11 119.0(3) . . ?
C11 C12 C13 121.0(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
O1 C2 C7 115.4(3) . . ?
O1 C2 C3 125.1(3) . . ?
C3 C2 C7 119.5(3) . . ?
C9 C8 C5 178.8(4) . . ?
C8 C9 C10 177.3(4) . . ?
C14 C13 Br1 120.7(2) . . ?
C12 C13 Br1 121.1(2) . . ?
C12 C13 C14 118.1(3) . . ?
F1 C11 C10 119.0(3) . . ?
F1 C11 C12 118.9(3) . . ?
C12 C11 C10 122.1(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F3 C15 C14 F4 1.0(4) . . . . ?
F3 C15 C14 C13 179.5(3) . . . . ?
F4 C14 C13 Br1 -1.1(4) . . . . ?
F4 C14 C13 C12 179.3(3) . . . . ?
F2 C12 C13 Br1 0.1(4) . . . . ?
F2 C12 C13 C14 179.7(3) . . . . ?
F2 C12 C11 F1 -0.3(5) . . . . ?
F2 C12 C11 C10 179.0(3) . . . . ?
C10 C15 C14 F4 -178.5(3) . . . . ?
C10 C15 C14 C13 0.0(5) . . . . ?
C15 C10 C11 F1 -179.0(3) . . . . ?
C15 C10 C11 C12 1.8(5) . . . . ?
C15 C14 C13 Br1 -179.6(2) . . . . ?
C15 C14 C13 C12 0.8(5) . . . . ?
C6 C5 C4 C3 0.5(5) . . . . ?
C6 C7 C2 O1 179.2(3) . . . . ?
C6 C7 C2 C3 0.6(5) . . . . ?
C2 C7 C6 C5 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C8 C5 C6 C7 179.3(3) . . . . ?
C8 C5 C4 C3 -179.1(3) . . . . ?
C9 C10 C15 F3 -2.4(5) . . . . ?
C9 C10 C15 C14 177.0(3) . . . . ?
C9 C10 C11 F1 2.7(5) . . . . ?
C9 C10 C11 C12 -176.5(3) . . . . ?
C13 C12 C11 F1 179.7(3) . . . . ?
C13 C12 C11 C10 -1.0(5) . . . . ?
C11 C10 C15 F3 179.3(3) . . . . ?
C11 C10 C15 C14 -1.3(5) . . . . ?
C11 C12 C13 Br1 -179.9(3) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C4 C3 C2 O1 -179.0(3) . . . . ?
C4 C3 C2 C7 -0.5(5) . . . . ?
C1 O1 C2 C7 178.9(3) . . . . ?
C1 O1 C2 C3 -2.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.805
_oxdiff_exptl_absorpt_empirical_full_min 0.566
