# 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_tol-5f-nb
_database_code_depnum_ccdc_archive 'CCDC 2118480'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_audit_creation_date             2020-12-01
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 F5 O2'
_chemical_formula_sum            'C17 H11 F5 O2'
_chemical_formula_weight         342.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H11F5O2
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'

_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                   8.9965(3)
_cell_length_b                   7.9831(3)
_cell_length_c                   21.5960(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.474(4)
_cell_angle_gamma                90
_cell_volume                     1546.30(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7136
_cell_measurement_temperature    299
_cell_measurement_theta_max      27.1040
_cell_measurement_theta_min      2.6960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25468
_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    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -8 20 0.3220
-2 -7 25 0.2922
-12 1 13 0.1481
-4 8 -20 0.3365
12 -2 -11 0.2013
0 -7 23 0.3066
-12 -1 9 0.0982
-3 7 -21 0.3561
3 7 -24 0.3678
12 1 -9 0.1602
-12 -2 5 0.1691
-12 -3 6 0.1623
12 -1 6 0.2858
-10 -7 -3 0.3062
9 1 19 0.3509
6 9 -10 0.3596
6 2 26 0.3498
3 11 -7 0.3775
6 -8 -17 0.2618
-6 5 25 0.2990
10 -3 -19 0.1980

_exptl_crystal_size_max          0.937
_exptl_crystal_size_mid          0.674
_exptl_crystal_size_min          0.259
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
3.8062 -7.5730 19.8106 -0.2276 -0.0248 0.9734
-2.0984 -6.5238 24.6067 0.2598 0.0270 0.9653
-11.8079 1.1116 12.8676 0.9870 0.1047 0.1222
-3.9001 7.5752 -19.6861 0.2355 0.0256 -0.9715
11.9562 -1.6306 -11.3521 -0.9930 -0.1054 -0.0529
-0.3961 -7.2273 23.3206 0.1112 0.0357 0.9932
-12.3435 -0.6551 9.0512 0.9436 0.3076 0.1228
-3.1899 7.2417 -21.3455 0.1607 0.0529 -0.9856
2.5465 6.9336 -23.5941 -0.2710 -0.0879 -0.9586
12.3446 0.6520 -9.0419 -0.9436 -0.3076 -0.1224
-11.9999 -2.0000 5.0006 0.8459 0.4570 0.1033
-11.9999 -3.0000 6.0006 0.8337 0.5018 0.1858
11.9999 -1.0000 5.9995 -0.7972 -0.4728 0.3438
-9.9999 -7.0000 -2.9997 0.5072 0.8546 0.2147
9.0000 1.0000 18.9999 -0.4038 -0.7381 0.5184
5.9999 9.0000 -10.0002 -0.3205 -0.5964 -0.6995
6.0000 2.0000 26.0002 -0.0970 -0.8272 0.6011
2.9999 11.0000 -7.0000 -0.0335 -0.6740 -0.7741
6.0000 -8.0000 -17.0008 -0.7821 0.6160 0.1056
-5.9999 5.0000 25.0008 0.7989 -0.5754 0.2667
9.9999 -3.0000 -19.0009 -0.9689 0.1944 -0.1869

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16469
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.271
_diffrn_ambient_temperature      299
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_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     47.00  74.00   0.25    1.21    --  -11.80  66.00  -2.00  108
  2  ω    -43.00 -18.00   0.25    1.21    --  -11.80  66.00  -2.00  100
  3  ω      9.00  35.00   0.25    1.21    --    5.00  57.00 -90.00  104
  4  ω     16.00  42.00   0.25    1.21    --    5.00  76.00-150.00  104
  5  ω      7.00  32.00   0.25    1.21    --    5.00  66.00  -2.00  100
  6  ω    -46.00  36.00   0.25    1.21    --  -11.80  57.00  60.00  328
  7  ω     21.00  71.00   0.25    1.21    --  -11.80  57.00-150.00  200
  8  ω     52.00  77.00   0.25    1.21    --  -11.80  57.00  60.00  100
  9  ω    -47.00  69.00   0.25    1.21    --  -11.80  57.00 -60.00  464
;
_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      -0.0698509000
_diffrn_orient_matrix_UB_12      0.0227693000
_diffrn_orient_matrix_UB_13      0.0106364000
_diffrn_orient_matrix_UB_21      -0.0353113000
_diffrn_orient_matrix_UB_22      -0.0635895000
_diffrn_orient_matrix_UB_23      -0.0187739000
_diffrn_orient_matrix_UB_31      0.0113851000
_diffrn_orient_matrix_UB_32      -0.0576207000
_diffrn_orient_matrix_UB_33      0.0249234000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                2396
_reflns_number_total             3541
_reflns_odcompleteness_completeness 99.84
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.095
_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)+(0.0790P)²+0.1650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1624
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00L(H00B,H00C), C00N(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00F(H00F), C00I(H00I)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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
O001 O 0.27878(13) 0.44720(15) 0.23476(5) 0.0725(3) Uani 1 1 d . . . . .
F002 F 0.93545(15) 0.60293(16) 0.55051(6) 0.0984(4) Uani 1 1 d . . . . .
F003 F 1.08240(13) 0.56068(18) 0.66169(6) 0.1037(4) Uani 1 1 d . . . . .
F004 F 1.01361(15) 0.30285(18) 0.73520(5) 0.1086(5) Uani 1 1 d . . . . .
F005 F 0.64991(17) 0.12431(18) 0.58435(7) 0.1155(5) Uani 1 1 d . . . . .
F006 F 0.7951(2) 0.08625(18) 0.69614(7) 0.1303(6) Uani 1 1 d . . . . .
C007 C 0.37187(17) 0.4446(2) 0.28737(7) 0.0601(4) Uani 1 1 d . . . . .
O2 O 0.2044(3) 0.3957(2) 0.10513(7) 0.1257(7) Uani 1 1 d . . . . .
C009 C 0.34202(17) 0.3216(2) 0.33015(7) 0.0622(4) Uani 1 1 d . . . . .
H009 H 0.2633 0.2476 0.3215 0.075 Uiso 1 1 calc R . . . .
C00A C 0.42789(18) 0.3091(2) 0.38500(8) 0.0668(4) Uani 1 1 d . . . . .
H00A H 0.4066 0.2266 0.4134 0.080 Uiso 1 1 calc R . . . .
C00B C 0.78943(18) 0.3631(2) 0.56300(8) 0.0674(4) Uani 1 1 d . . . . .
C00C C 0.54637(18) 0.4176(2) 0.39898(8) 0.0669(4) Uani 1 1 d . . . . .
C00D C 0.90160(19) 0.4712(2) 0.58490(8) 0.0681(4) Uani 1 1 d . . . . .
C00E C 0.97716(18) 0.4512(2) 0.64178(9) 0.0723(5) Uani 1 1 d . . . . .
C00F C 0.48970(19) 0.5532(2) 0.30058(9) 0.0716(4) Uani 1 1 d . . . . .
H00F H 0.5109 0.6355 0.2721 0.086 Uiso 1 1 calc R . . . .
C00G C 0.9426(2) 0.3219(2) 0.67929(8) 0.0760(5) Uani 1 1 d . . . . .
C00H C 0.6358(2) 0.4026(2) 0.45668(8) 0.0744(5) Uani 1 1 d . . . . .
C00I C 0.57550(19) 0.5396(2) 0.35589(9) 0.0740(5) Uani 1 1 d . . . . .
H00I H 0.6544 0.6134 0.3645 0.089 Uiso 1 1 calc R . . . .
C00J C 0.7081(2) 0.3854(2) 0.50456(8) 0.0758(5) Uani 1 1 d . . . . .
C00K C 0.7581(2) 0.2331(2) 0.60216(9) 0.0778(5) Uani 1 1 d . . . . .
C00L C 0.3063(2) 0.5675(2) 0.18808(9) 0.0789(5) Uani 1 1 d . . . . .
H00B H 0.4045 0.5500 0.1736 0.095 Uiso 1 1 calc R . . . .
H00C H 0.3024 0.6799 0.2050 0.095 Uiso 1 1 calc R . . . .
C00M C 0.8325(2) 0.2127(2) 0.65939(9) 0.0840(5) Uani 1 1 d . . . . .
C00N C 0.1907(3) 0.5472(2) 0.13600(9) 0.0858(6) Uani 1 1 d . . . . .
H00D H 0.0929 0.5532 0.1519 0.103 Uiso 1 1 calc R . . . .
H00E H 0.1985 0.6386 0.1068 0.103 Uiso 1 1 calc R . . . .
C10 C 0.2086(7) 0.3932(4) 0.04747(14) 0.192(2) Uani 1 1 d . . . . .
H10A H 0.1181 0.4400 0.0283 0.289 Uiso 1 1 calc GR . . . .
H10B H 0.2189 0.2796 0.0338 0.289 Uiso 1 1 calc GR . . . .
H10C H 0.2921 0.4579 0.0360 0.289 Uiso 1 1 calc GR . . . .


_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
O001 C007 1.3581(19) . ?
O001 C00L 1.428(2) . ?
F002 C00D 1.336(2) . ?
F003 C00E 1.335(2) . ?
F004 C00G 1.330(2) . ?
F005 C00K 1.338(2) . ?
F006 C00M 1.343(2) . ?
C007 C009 1.388(2) . ?
C007 C00F 1.382(2) . ?
O2 C00N 1.391(2) . ?
O2 C10 1.249(3) . ?
C009 H009 0.9300 . ?
C009 C00A 1.366(2) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.388(2) . ?
C00B C00D 1.383(2) . ?
C00B C00J 1.420(2) . ?
C00B C00K 1.381(3) . ?
C00C C00H 1.435(2) . ?
C00C C00I 1.386(3) . ?
C00D C00E 1.366(2) . ?
C00E C00G 1.362(3) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.375(3) . ?
C00G C00M 1.364(3) . ?
C00H C00J 1.186(2) . ?
C00I H00I 0.9300 . ?
C00K C00M 1.368(3) . ?
C00L H00B 0.9700 . ?
C00L H00C 0.9700 . ?
C00L C00N 1.480(3) . ?
C00N H00D 0.9700 . ?
C00N H00E 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C007 O001 C00L 118.12(13) . . ?
O001 C007 C009 115.41(13) . . ?
O001 C007 C00F 125.15(15) . . ?
C00F C007 C009 119.44(15) . . ?
C10 O2 C00N 120.2(2) . . ?
C007 C009 H009 119.9 . . ?
C00A C009 C007 120.20(15) . . ?
C00A C009 H009 119.9 . . ?
C009 C00A H00A 119.5 . . ?
C009 C00A C00C 121.02(16) . . ?
C00C C00A H00A 119.5 . . ?
C00D C00B C00J 122.50(18) . . ?
C00K C00B C00D 115.95(15) . . ?
C00K C00B C00J 121.54(17) . . ?
C00A C00C C00H 120.38(17) . . ?
C00I C00C C00A 118.33(16) . . ?
C00I C00C C00H 121.29(16) . . ?
F002 C00D C00B 119.53(15) . . ?
F002 C00D C00E 118.21(16) . . ?
C00E C00D C00B 122.23(17) . . ?
F003 C00E C00D 120.24(18) . . ?
F003 C00E C00G 119.56(17) . . ?
C00G C00E C00D 120.17(17) . . ?
C007 C00F H00F 120.0 . . ?
C00I C00F C007 119.93(17) . . ?
C00I C00F H00F 120.0 . . ?
F004 C00G C00E 120.72(18) . . ?
F004 C00G C00M 119.90(19) . . ?
C00E C00G C00M 119.37(17) . . ?
C00J C00H C00C 178.0(2) . . ?
C00C C00I H00I 119.5 . . ?
C00F C00I C00C 121.09(16) . . ?
C00F C00I H00I 119.5 . . ?
C00H C00J C00B 177.7(2) . . ?
F005 C00K C00B 119.34(17) . . ?
F005 C00K C00M 118.41(19) . . ?
C00M C00K C00B 122.24(18) . . ?
O001 C00L H00B 110.1 . . ?
O001 C00L H00C 110.1 . . ?
O001 C00L C00N 108.19(15) . . ?
H00B C00L H00C 108.4 . . ?
C00N C00L H00B 110.1 . . ?
C00N C00L H00C 110.1 . . ?
F006 C00M C00G 120.23(18) . . ?
F006 C00M C00K 119.7(2) . . ?
C00G C00M C00K 120.04(19) . . ?
O2 C00N C00L 112.08(18) . . ?
O2 C00N H00D 109.2 . . ?
O2 C00N H00E 109.2 . . ?
C00L C00N H00D 109.2 . . ?
C00L C00N H00E 109.2 . . ?
H00D C00N H00E 107.9 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_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 2.326
_oxdiff_exptl_absorpt_empirical_full_min 0.404
####################################################################### 
# 
# 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_tol-5f-mande-s
_database_code_depnum_ccdc_archive 'CCDC 2118482'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_audit_creation_date             2020-11-30
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 F5 O2'
_chemical_formula_sum            'C23 H15 F5 O2'
_chemical_formula_weight         418.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H15F5O2
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'

_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                   8.9679(5)
_cell_length_b                   9.2898(4)
_cell_length_c                   11.8018(5)
_cell_angle_alpha                88.321(4)
_cell_angle_beta                 83.008(4)
_cell_angle_gamma                84.421(4)
_cell_volume                     971.12(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5939
_cell_measurement_temperature    299
_cell_measurement_theta_max      27.1360
_cell_measurement_theta_min      2.1640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68481
_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    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12 -3 -2 0.2918
-2 2 16 0.1260
-11 1 -9 0.3049
0 -2 -16 0.1710
13 0 2 0.3189
9 -8 3 0.3101
-3 -13 2 0.2820
-11 -8 -1 0.3090
-13 -2 -2 0.3088
-1 13 -2 0.2242
1 -10 -10 0.1935
-10 -6 -10 0.3175
0 -5 -15 0.1761
1 5 -15 0.2117
-3 -4 14 0.2015
12 0 -4 0.2943

_exptl_crystal_size_max          0.713
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.335
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
11.6459 -2.6448 -2.4548 -0.2687 0.1183 0.9559
-1.8367 2.2346 15.8070 0.9031 -0.4008 -0.1541
-11.1805 1.2177 -8.8542 -0.3678 0.1643 -0.9153
-0.1581 -1.9016 -16.4048 -0.9139 0.4058 -0.0094
12.5998 0.1945 2.1406 -0.0745 -0.1679 0.9830
9.1526 -7.9780 2.9032 0.1923 0.4331 0.8806
-3.3407 -12.7697 1.5443 0.4058 0.9140 0.0003
-10.6943 -7.9490 -0.5244 0.2995 0.6747 -0.6746
-12.6313 -1.8274 -1.8749 0.1242 0.2799 -0.9519
-1.3802 12.6779 -2.3432 -0.3773 -0.8498 -0.3682
1.0000 -10.0000 -10.0000 -0.3913 0.8655 0.2579
-10.0000 -6.0000 -10.0000 -0.3036 0.6850 -0.6802
-0.0000 -5.0000 -15.0000 -0.7705 0.6015 0.0684
1.0000 5.0000 -15.0000 -0.9927 -0.1188 -0.0552
-3.0000 -4.0000 14.0000 0.9448 0.0830 -0.1230
12.0000 -0.0000 -4.0000 -0.4189 -0.0477 0.9269

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14654
_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         27.484
_diffrn_reflns_theta_min         2.203
_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     40.00  75.00   0.25    0.73    --    5.00  76.00-180.00  140
  2  ω     44.00  72.00   0.25    0.73    --    5.00  57.00 -30.00  112
  3  ω     -9.00  27.00   0.25    0.73    --    5.00  76.00-180.00  144
  4  ω    -47.00 -10.00   0.25    0.73    --  -11.80  57.00  60.00  148
  5  ω    -46.00  24.00   0.25    0.73    --  -11.80  57.00 -60.00  280
  6  ω    -48.00   8.00   0.25    0.73    --  -11.80  76.00  90.00  224
  7  ω    -53.00  68.00   0.25    0.73    --  -11.80  76.00 150.00  484
  8  ω    -88.00  75.00   0.25    0.73    --  -11.80  -1.00 120.00  652
;
_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      -0.0154908000
_diffrn_orient_matrix_UB_12      -0.0206802000
_diffrn_orient_matrix_UB_13      0.0582570000
_diffrn_orient_matrix_UB_21      -0.0094437000
_diffrn_orient_matrix_UB_22      -0.0710863000
_diffrn_orient_matrix_UB_23      -0.0164042000
_diffrn_orient_matrix_UB_31      0.0779598000
_diffrn_orient_matrix_UB_32      -0.0201559000
_diffrn_orient_matrix_UB_33      0.0021580000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                3115
_reflns_number_total             4447
_reflns_odcompleteness_completeness 99.71
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.064
_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)+(0.0700P)²+0.0750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1381
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00B,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00F(H00F), C00I(H00I), C00J(H00J), C00O(H00O),
 C00R(H00R), C00S(H00S), C00T(H00T)
2.d Idealised Me refined as rotating group:
 C00U(H00G,H00H,H00K)
;
_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
O001 O 0.41380(11) 1.01935(10) 0.20062(9) 0.0602(3) Uani 1 1 d . . . . .
F002 F 0.91913(12) 0.55322(11) 0.66739(9) 0.0839(3) Uani 1 1 d . . . . .
F003 F 0.75086(13) 0.17682(12) 0.47487(9) 0.0913(3) Uani 1 1 d . . . . .
F004 F 0.89492(14) -0.01777(11) 0.60492(10) 0.1013(4) Uani 1 1 d . . . . .
F005 F 1.06604(13) 0.35732(16) 0.79631(9) 0.1059(4) Uani 1 1 d . . . . .
F006 F 1.05713(14) 0.07260(14) 0.76470(10) 0.1110(4) Uani 1 1 d . . . . .
O007 O 0.36617(14) 1.39513(11) 0.13147(11) 0.0830(4) Uani 1 1 d . . . . .
C008 C 0.48589(15) 0.91493(14) 0.26362(11) 0.0521(3) Uani 1 1 d . . . . .
C009 C 0.61346(15) 1.17983(13) 0.15634(11) 0.0524(3) Uani 1 1 d . . . . .
C00A C 0.45216(16) 1.16571(14) 0.20421(12) 0.0573(3) Uani 1 1 d . . . . .
H00A H 0.4345 1.1994 0.2830 0.069 Uiso 1 1 calc R . . . .
C00B C 0.83020(15) 0.37076(15) 0.56713(12) 0.0563(3) Uani 1 1 d . . . . .
C00C C 0.61706(16) 0.68418(15) 0.38447(12) 0.0574(3) Uani 1 1 d . . . . .
C00D C 0.67408(17) 1.11022(16) 0.05729(12) 0.0610(4) Uani 1 1 d . . . . .
H00D H 0.6154 1.0523 0.0217 0.073 Uiso 1 1 calc R . . . .
C00E C 0.56861(17) 0.94115(15) 0.35082(12) 0.0610(4) Uani 1 1 d . . . . .
H00E H 0.5806 1.0356 0.3693 0.073 Uiso 1 1 calc R . . . .
C00F C 0.46891(16) 0.77346(15) 0.23663(13) 0.0582(3) Uani 1 1 d . . . . .
H00F H 0.4136 0.7557 0.1776 0.070 Uiso 1 1 calc R . . . .
C00G C 0.82795(17) 0.22396(17) 0.55367(12) 0.0621(4) Uani 1 1 d . . . . .
C00H C 0.91224(17) 0.41212(16) 0.65125(13) 0.0622(4) Uani 1 1 d . . . . .
C00I C 0.53308(17) 0.65964(15) 0.29624(13) 0.0623(4) Uani 1 1 d . . . . .
H00I H 0.5204 0.5654 0.2776 0.075 Uiso 1 1 calc R . . . .
C00J C 0.63344(18) 0.82634(16) 0.41043(12) 0.0623(4) Uani 1 1 d . . . . .
H00J H 0.6892 0.8445 0.4691 0.075 Uiso 1 1 calc R . . . .
C00K C 0.75154(16) 0.47582(16) 0.50045(13) 0.0614(4) Uani 1 1 d . . . . .
C00L C 0.68837(17) 0.56832(16) 0.44685(13) 0.0620(4) Uani 1 1 d . . . . .
C00M C 0.34085(18) 1.24903(16) 0.13340(15) 0.0674(4) Uani 1 1 d . . . . .
H00B H 0.3546 1.2126 0.0563 0.081 Uiso 1 1 calc R . . . .
H00C H 0.2383 1.2371 0.1666 0.081 Uiso 1 1 calc R . . . .
C00N C 0.9017(2) 0.12325(17) 0.61932(14) 0.0704(4) Uani 1 1 d . . . . .
C00O C 0.7031(2) 1.26472(16) 0.20754(15) 0.0720(4) Uani 1 1 d . . . . .
H00O H 0.6654 1.3123 0.2747 0.086 Uiso 1 1 calc R . . . .
C00P C 0.98730(18) 0.3130(2) 0.71688(13) 0.0703(4) Uani 1 1 d . . . . .
C00Q C 0.98252(19) 0.1686(2) 0.70135(14) 0.0742(5) Uani 1 1 d . . . . .
C00R C 0.81960(19) 1.1249(2) 0.01034(16) 0.0770(5) Uani 1 1 d . . . . .
H00R H 0.8583 1.0767 -0.0564 0.092 Uiso 1 1 calc R . . . .
C00S C 0.8514(2) 1.2789(2) 0.1577(2) 0.0929(7) Uani 1 1 d . . . . .
H00S H 0.9119 1.3367 0.1917 0.111 Uiso 1 1 calc R . . . .
C00T C 0.9068(2) 1.2084(2) 0.0599(2) 0.0904(6) Uani 1 1 d . . . . .
H00T H 1.0052 1.2179 0.0272 0.108 Uiso 1 1 calc R . . . .
C00U C 0.2898(2) 1.4752(2) 0.04986(19) 0.0939(6) Uani 1 1 d . . . . .
H00G H 0.3140 1.4299 -0.0230 0.141 Uiso 1 1 calc GR . . . .
H00H H 0.3203 1.5717 0.0444 0.141 Uiso 1 1 calc GR . . . .
H00K H 0.1830 1.4789 0.0724 0.141 Uiso 1 1 calc GR . . . .


_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
O001 C008 1.3655(16) . ?
O001 C00A 1.4376(16) . ?
F002 C00H 1.3385(17) . ?
F003 C00G 1.3319(18) . ?
F004 C00N 1.3341(19) . ?
F005 C00P 1.3369(19) . ?
F006 C00Q 1.3301(17) . ?
O007 C00M 1.3968(19) . ?
O007 C00U 1.403(2) . ?
C008 C00E 1.380(2) . ?
C008 C00F 1.3881(19) . ?
C009 C00A 1.504(2) . ?
C009 C00D 1.379(2) . ?
C009 C00O 1.379(2) . ?
C00A H00A 0.9800 . ?
C00A C00M 1.519(2) . ?
C00B C00G 1.380(2) . ?
C00B C00H 1.389(2) . ?
C00B C00K 1.4233(19) . ?
C00C C00I 1.393(2) . ?
C00C C00J 1.390(2) . ?
C00C C00L 1.430(2) . ?
C00D H00D 0.9300 . ?
C00D C00R 1.372(2) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.380(2) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.371(2) . ?
C00G C00N 1.369(2) . ?
C00H C00P 1.366(2) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K C00L 1.192(2) . ?
C00M H00B 0.9700 . ?
C00M H00C 0.9700 . ?
C00N C00Q 1.376(3) . ?
C00O H00O 0.9300 . ?
C00O C00S 1.404(3) . ?
C00P C00Q 1.364(2) . ?
C00R H00R 0.9300 . ?
C00R C00T 1.346(3) . ?
C00S H00S 0.9300 . ?
C00S C00T 1.360(3) . ?
C00T H00T 0.9300 . ?
C00U H00G 0.9600 . ?
C00U H00H 0.9600 . ?
C00U H00K 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
C008 O001 C00A 118.92(10) . . ?
C00M O007 C00U 112.15(14) . . ?
O001 C008 C00E 124.89(13) . . ?
O001 C008 C00F 115.40(12) . . ?
C00E C008 C00F 119.69(12) . . ?
C00D C009 C00A 120.13(12) . . ?
C00D C009 C00O 118.28(14) . . ?
C00O C009 C00A 121.57(14) . . ?
O001 C00A C009 111.97(11) . . ?
O001 C00A H00A 109.7 . . ?
O001 C00A C00M 103.10(11) . . ?
C009 C00A H00A 109.7 . . ?
C009 C00A C00M 112.34(12) . . ?
C00M C00A H00A 109.7 . . ?
C00G C00B C00H 116.42(13) . . ?
C00G C00B C00K 122.58(14) . . ?
C00H C00B C00K 120.99(14) . . ?
C00I C00C C00L 122.11(13) . . ?
C00J C00C C00I 118.35(13) . . ?
C00J C00C C00L 119.53(13) . . ?
C009 C00D H00D 119.4 . . ?
C00R C00D C009 121.10(15) . . ?
C00R C00D H00D 119.4 . . ?
C008 C00E H00E 120.2 . . ?
C008 C00E C00J 119.62(13) . . ?
C00J C00E H00E 120.2 . . ?
C008 C00F H00F 119.7 . . ?
C00I C00F C008 120.54(13) . . ?
C00I C00F H00F 119.7 . . ?
F003 C00G C00B 119.54(13) . . ?
F003 C00G C00N 118.05(15) . . ?
C00N C00G C00B 122.40(15) . . ?
F002 C00H C00B 118.91(13) . . ?
F002 C00H C00P 119.19(15) . . ?
C00P C00H C00B 121.89(15) . . ?
C00C C00I H00I 119.7 . . ?
C00F C00I C00C 120.51(13) . . ?
C00F C00I H00I 119.7 . . ?
C00C C00J H00J 119.4 . . ?
C00E C00J C00C 121.28(13) . . ?
C00E C00J H00J 119.4 . . ?
C00L C00K C00B 177.17(17) . . ?
C00K C00L C00C 177.22(17) . . ?
O007 C00M C00A 108.52(13) . . ?
O007 C00M H00B 110.0 . . ?
O007 C00M H00C 110.0 . . ?
C00A C00M H00B 110.0 . . ?
C00A C00M H00C 110.0 . . ?
H00B C00M H00C 108.4 . . ?
F004 C00N C00G 120.63(17) . . ?
F004 C00N C00Q 119.96(15) . . ?
C00G C00N C00Q 119.40(15) . . ?
C009 C00O H00O 120.2 . . ?
C009 C00O C00S 119.70(17) . . ?
C00S C00O H00O 120.2 . . ?
F005 C00P C00H 120.02(17) . . ?
F005 C00P C00Q 119.84(15) . . ?
C00Q C00P C00H 120.14(15) . . ?
F006 C00Q C00N 120.38(17) . . ?
F006 C00Q C00P 119.87(18) . . ?
C00P C00Q C00N 119.75(14) . . ?
C00D C00R H00R 119.7 . . ?
C00T C00R C00D 120.65(19) . . ?
C00T C00R H00R 119.7 . . ?
C00O C00S H00S 119.9 . . ?
C00T C00S C00O 120.13(17) . . ?
C00T C00S H00S 119.9 . . ?
C00R C00T C00S 120.14(18) . . ?
C00R C00T H00T 119.9 . . ?
C00S C00T H00T 119.9 . . ?
O007 C00U H00G 109.5 . . ?
O007 C00U H00H 109.5 . . ?
O007 C00U H00K 109.5 . . ?
H00G C00U H00H 109.5 . . ?
H00G C00U H00K 109.5 . . ?
H00H C00U H00K 109.5 . . ?

_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.575
####################################################################### 
# 
# 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_346
_database_code_depnum_ccdc_archive 'CCDC 2118481'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-01-25 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         'C18 H13 F5 O2'
_chemical_formula_sum            'C18 H13 F5 O2'
_chemical_formula_weight         356.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H13F5O2
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'

_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                   7.5715(6)
_cell_length_b                   10.6727(6)
_cell_length_c                   11.9855(7)
_cell_angle_alpha                65.696(6)
_cell_angle_beta                 71.888(6)
_cell_angle_gamma                76.943(6)
_cell_volume                     833.57(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4270
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1430
_cell_measurement_theta_min      2.8270
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81370
_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    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 -7 7 0.3331
10 3 11 0.3215
8 12 9 0.2689
0 14 0 0.1771
-10 -7 -11 0.2997
0 -14 0 0.2451
11 3 4 0.2603
0 6 16 0.2610
-11 -4 -5 0.2623
-1 -6 -16 0.2173
0 -6 11 0.2226
8 9 0 0.2128
9 9 3 0.2284
-8 -9 0 0.2904
0 -15 -7 0.2704
8 -7 3 0.3217
9 6 -1 0.1995
-1 -2 14 0.2188

_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.481
_exptl_crystal_size_min          0.43
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
6.3615 -6.9098 7.3243 -0.7167 0.3175 0.6209
9.6875 2.9499 10.9813 -0.1843 0.0808 0.9795
7.8073 12.4470 8.7211 0.5295 -0.2359 0.8149
-0.0807 13.5221 -0.2648 0.9136 -0.4057 0.0260
-9.7511 -6.9328 -11.0027 -0.0814 0.0372 -0.9960
-0.3316 -13.7371 -0.2014 -0.9118 0.4049 -0.0680
10.6377 3.3722 3.9897 -0.1871 -0.4216 0.8873
0.4631 5.8929 16.2679 0.3661 0.8246 0.4313
-10.6603 -3.5859 -4.5764 0.1741 0.3922 -0.9033
-0.5891 -5.9347 -16.3203 -0.3640 -0.8199 -0.4419
0.0000 -6.0000 11.0000 -0.4125 0.8649 0.2403
8.0000 9.0000 -0.0000 0.2968 -0.6934 0.6153
9.0000 9.0000 3.0000 0.2558 -0.5591 0.7593
-8.0000 -9.0000 0.0000 -0.2968 0.6934 -0.6153
-0.0000 -15.0000 -7.0000 -1.0044 -0.0029 -0.2061
8.0000 -7.0000 3.0000 -0.7827 -0.0396 0.6403
9.0000 6.0000 -1.0000 0.0570 -0.7228 0.6572
-1.0000 -2.0000 14.0000 -0.1069 0.9908 0.2481

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10966
_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         2.270
_diffrn_ambient_temperature      293(2)
_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    -14.00  27.00   0.25    0.80    --    5.00  76.00  90.00  164
  2  ω    -53.00  -1.00   0.25    0.80    --  -11.60  76.00 -30.00  208
  3  ω     48.00  74.00   0.25    0.80    --  -11.60  76.00 -30.00  104
  4  ω    -47.00  43.00   0.25    0.80    --  -11.60  57.00  90.00  360
  5  ω    -44.00  54.00   0.25    0.80    --  -11.60  57.00-180.00  392
  6  ω    -94.00  74.00   0.25    0.80    --  -11.60  19.00   0.00  672
;
_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      -0.0386389000
_diffrn_orient_matrix_UB_12      0.0673212000
_diffrn_orient_matrix_UB_13      -0.0007800000
_diffrn_orient_matrix_UB_21      -0.0539462000
_diffrn_orient_matrix_UB_22      -0.0290937000
_diffrn_orient_matrix_UB_23      0.0627623000
_diffrn_orient_matrix_UB_31      0.0737407000
_diffrn_orient_matrix_UB_32      0.0028240000
_diffrn_orient_matrix_UB_33      0.0233901000
_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                2271
_reflns_number_total             3806
_reflns_odcompleteness_completeness 99.66
_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         0.853
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1695
_refine_ls_R_factor_gt           0.1432
_refine_ls_restrained_S_all      1.933
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4805
_refine_ls_wR_factor_ref         0.5001
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00B,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00E(H00E), C00H(H00H)
2.d Idealised Me refined as rotating group:
 C00N(H00F,H00G,H00J), C2(H2A,H2B,H2C)
;
_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
O001 O 0.4427(5) 1.0898(3) 0.1424(3) 0.0978(10) Uani 1 1 d . . . . .
F002 F 0.7151(7) 0.4002(5) 0.7737(4) 0.1603(18) Uani 1 1 d . . . . .
F003 F 1.0286(5) -0.0406(3) 0.8427(4) 0.1439(14) Uani 1 1 d . . . . .
F004 F 0.9817(7) 0.2517(4) 0.4373(4) 0.1522(16) Uani 1 1 d . . . . .
C005 C 0.8409(5) 0.3345(4) 0.5998(4) 0.0800(11) Uani 1 1 d . . . . .
C006 C 0.5077(6) 0.9666(4) 0.2232(4) 0.0842(11) Uani 1 1 d . . . . .
F007 F 1.1018(7) 0.0079(4) 0.5929(6) 0.1666(18) Uani 1 1 d . . . . .
C008 C 0.6441(5) 0.7075(4) 0.3737(4) 0.0803(11) Uani 1 1 d . . . . .
F009 F 0.8438(7) 0.1577(6) 0.9316(3) 0.186(2) Uani 1 1 d . . . . .
C00A C 0.4820(7) 0.9354(5) 0.3509(4) 0.0878(12) Uani 1 1 d . . . . .
H00A H 0.417187 1.000170 0.386796 0.105 Uiso 1 1 calc R U . . .
C00B C 0.9390(6) 0.2305(5) 0.5596(4) 0.0916(13) Uani 1 1 d . . . . .
C00C C 0.5537(7) 0.8062(5) 0.4253(4) 0.0933(13) Uani 1 1 d . . . . .
H00C H 0.540466 0.786219 0.510463 0.112 Uiso 1 1 calc R U . . .
C00D C 0.8115(6) 0.3053(6) 0.7267(4) 0.0988(14) Uani 1 1 d . . . . .
C00E C 0.5988(6) 0.8696(4) 0.1730(4) 0.0841(11) Uani 1 1 d . . . . .
H00E H 0.617297 0.891254 0.086933 0.101 Uiso 1 1 calc R U . . .
C00F C 0.7156(5) 0.5740(4) 0.4517(4) 0.0870(12) Uani 1 1 d . . . . .
C00G C 0.7729(6) 0.4671(4) 0.5183(4) 0.0885(12) Uani 1 1 d . . . . .
C00H C 0.6648(6) 0.7394(5) 0.2467(4) 0.0879(12) Uani 1 1 d . . . . .
H00H H 0.722860 0.673438 0.210827 0.105 Uiso 1 1 calc R U . . .
C00I C 0.3787(7) 1.2063(5) 0.1800(5) 0.0983(13) Uani 1 1 d . . . . .
H00I H 0.296448 1.178971 0.265362 0.118 Uiso 1 1 calc R U . . .
C00J C 0.9658(6) 0.0817(5) 0.7637(5) 0.0966(14) Uani 1 1 d . . . . .
C00K C 1.0040(7) 0.1061(5) 0.6379(6) 0.1026(15) Uani 1 1 d . . . . .
C00L C 0.8724(7) 0.1813(6) 0.8075(4) 0.1084(17) Uani 1 1 d . . . . .
C00M C 0.5442(13) 1.2621(8) 0.1761(8) 0.148(3) Uani 1 1 d . . . . .
H00B H 0.646329 1.187902 0.183579 0.177 Uiso 1 1 calc R U . . .
H00D H 0.579815 1.332910 0.093019 0.177 Uiso 1 1 calc R U . . .
C00N C 0.2651(16) 1.3045(7) 0.0816(9) 0.178(4) Uani 1 1 d . . . . .
H00F H 0.345406 1.325721 -0.002005 0.266 Uiso 1 1 calc R U . . .
H00G H 0.216770 1.388420 0.097451 0.266 Uiso 1 1 calc R U . . .
H00J H 0.163313 1.259644 0.088835 0.266 Uiso 1 1 calc R U . . .
O00O O 0.5340(17) 1.3072(17) 0.2469(9) 0.279(6) Uani 1 1 d . . . . .
C2 C 0.676(3) 1.376(2) 0.2422(13) 0.259(8) Uani 1 1 d . . . . .
H2A H 0.675465 1.466052 0.176007 0.389 Uiso 1 1 calc R U . . .
H2B H 0.795160 1.323496 0.225706 0.389 Uiso 1 1 calc R U . . .
H2C H 0.654029 1.386308 0.321540 0.389 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
O001 C006 1.365(5) . ?
O001 C00I 1.428(5) . ?
F002 C00D 1.325(6) . ?
F003 C00J 1.345(5) . ?
F004 C00B 1.330(6) . ?
C005 C00B 1.365(6) . ?
C005 C00D 1.374(6) . ?
C005 C00G 1.438(5) . ?
C006 C00A 1.383(6) . ?
C006 C00E 1.358(6) . ?
F007 C00K 1.344(6) . ?
C008 C00C 1.381(7) . ?
C008 C00F 1.438(6) . ?
C008 C00H 1.381(6) . ?
F009 C00L 1.355(7) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.393(6) . ?
C00B C00K 1.360(7) . ?
C00C H00C 0.9300 . ?
C00D C00L 1.360(7) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.383(6) . ?
C00F C00G 1.170(6) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9800 . ?
C00I C00M 1.485(10) . ?
C00I C00N 1.560(10) . ?
C00J C00K 1.365(8) . ?
C00J C00L 1.341(8) . ?
C00M H00B 0.9700 . ?
C00M H00D 0.9700 . ?
C00M O00O 1.112(11) . ?
C00N H00F 0.9600 . ?
C00N H00G 0.9600 . ?
C00N H00J 0.9600 . ?
O00O C2 1.410(13) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
C006 O001 C00I 120.2(3) . . ?
C00B C005 C00D 115.2(4) . . ?
C00B C005 C00G 124.0(4) . . ?
C00D C005 C00G 120.8(4) . . ?
O001 C006 C00A 124.1(4) . . ?
C00E C006 O001 116.4(4) . . ?
C00E C006 C00A 119.4(4) . . ?
C00C C008 C00F 120.1(4) . . ?
C00H C008 C00C 119.0(4) . . ?
C00H C008 C00F 120.9(4) . . ?
C006 C00A H00A 120.2 . . ?
C006 C00A C00C 119.6(4) . . ?
C00C C00A H00A 120.2 . . ?
F004 C00B C005 119.3(4) . . ?
F004 C00B C00K 117.3(5) . . ?
C00K C00B C005 123.3(4) . . ?
C008 C00C C00A 120.6(4) . . ?
C008 C00C H00C 119.7 . . ?
C00A C00C H00C 119.7 . . ?
F002 C00D C005 119.0(4) . . ?
F002 C00D C00L 118.1(4) . . ?
C00L C00D C005 122.9(5) . . ?
C006 C00E H00E 119.2 . . ?
C006 C00E C00H 121.5(4) . . ?
C00H C00E H00E 119.2 . . ?
C00G C00F C008 177.8(5) . . ?
C00F C00G C005 178.9(4) . . ?
C008 C00H C00E 119.8(4) . . ?
C008 C00H H00H 120.1 . . ?
C00E C00H H00H 120.1 . . ?
O001 C00I H00I 110.3 . . ?
O001 C00I C00M 108.4(5) . . ?
O001 C00I C00N 102.4(4) . . ?
C00M C00I H00I 110.3 . . ?
C00M C00I C00N 114.9(6) . . ?
C00N C00I H00I 110.3 . . ?
F003 C00J C00K 119.9(5) . . ?
C00L C00J F003 120.0(5) . . ?
C00L C00J C00K 120.0(4) . . ?
F007 C00K C00B 120.7(5) . . ?
F007 C00K C00J 120.3(5) . . ?
C00B C00K C00J 118.9(5) . . ?
F009 C00L C00D 121.1(6) . . ?
C00J C00L F009 119.3(5) . . ?
C00J C00L C00D 119.7(5) . . ?
C00I C00M H00B 107.5 . . ?
C00I C00M H00D 107.5 . . ?
H00B C00M H00D 107.0 . . ?
O00O C00M C00I 119.2(8) . . ?
O00O C00M H00B 107.5 . . ?
O00O C00M H00D 107.5 . . ?
C00I C00N H00F 109.5 . . ?
C00I C00N H00G 109.5 . . ?
C00I C00N H00J 109.5 . . ?
H00F C00N H00G 109.5 . . ?
H00F C00N H00J 109.5 . . ?
H00G C00N H00J 109.5 . . ?
C00M O00O C2 123.2(12) . . ?
O00O C2 H2A 109.5 . . ?
O00O C2 H2B 109.5 . . ?
O00O C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 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
O001 C006 C00A C00C 179.8(4) . . . . ?
O001 C006 C00E C00H -177.6(4) . . . . ?
O001 C00I C00M O00O -145.6(12) . . . . ?
F002 C00D C00L F009 -3.3(9) . . . . ?
F002 C00D C00L C00J 178.1(5) . . . . ?
F003 C00J C00K F007 1.0(7) . . . . ?
F003 C00J C00K C00B 179.9(4) . . . . ?
F003 C00J C00L F009 0.6(8) . . . . ?
F003 C00J C00L C00D 179.2(4) . . . . ?
F004 C00B C00K F007 -2.3(7) . . . . ?
F004 C00B C00K C00J 178.8(4) . . . . ?
C005 C00B C00K F007 -179.2(4) . . . . ?
C005 C00B C00K C00J 1.8(7) . . . . ?
C005 C00D C00L F009 178.6(5) . . . . ?
C005 C00D C00L C00J 0.1(8) . . . . ?
C006 O001 C00I C00M 74.8(6) . . . . ?
C006 O001 C00I C00N -163.4(5) . . . . ?
C006 C00A C00C C008 -2.4(7) . . . . ?
C006 C00E C00H C008 -2.3(7) . . . . ?
C00A C006 C00E C00H 0.8(7) . . . . ?
C00B C005 C00D F002 -179.1(5) . . . . ?
C00B C005 C00D C00L -1.0(7) . . . . ?
C00C C008 C00H C00E 1.4(6) . . . . ?
C00D C005 C00B F004 -176.9(4) . . . . ?
C00D C005 C00B C00K 0.1(7) . . . . ?
C00E C006 C00A C00C 1.5(7) . . . . ?
C00F C008 C00C C00A -179.3(3) . . . . ?
C00F C008 C00H C00E -178.5(4) . . . . ?
C00G C005 C00B F004 2.4(6) . . . . ?
C00G C005 C00B C00K 179.3(4) . . . . ?
C00G C005 C00D F002 1.7(7) . . . . ?
C00G C005 C00D C00L 179.7(4) . . . . ?
C00H C008 C00C C00A 0.9(6) . . . . ?
C00I O001 C006 C00A 14.0(6) . . . . ?
C00I O001 C006 C00E -167.7(4) . . . . ?
C00I C00M O00O C2 -172.7(13) . . . . ?
C00K C00J C00L F009 -176.7(5) . . . . ?
C00K C00J C00L C00D 1.9(8) . . . . ?
C00L C00J C00K F007 178.3(5) . . . . ?
C00L C00J C00K C00B -2.8(7) . . . . ?
C00N C00I C00M O00O 100.5(13) . . . . ?

_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 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.814
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rac-cn
_database_code_depnum_ccdc_archive 'CCDC 2118483'
loop_
_audit_author_name
_audit_author_address
'Masato Morita'
;Kyoto Institute of Technology
Japan
;
_audit_update_record             
;
2021-10-29 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;
_audit_creation_date             2020-10-18
_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         'C19 H11 F4 N O2'
_chemical_formula_sum            'C19 H11 F4 N O2'
_chemical_formula_weight         361.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H11F4NO2
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'
N N 0.0061 0.0033 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.1206(3)
_cell_length_b                   22.0913(10)
_cell_length_c                   11.8054(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.582(5)
_cell_angle_gamma                90
_cell_volume                     1582.28(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5779
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.2160
_cell_measurement_theta_min      2.7690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83662
_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    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-9 1 0 0.2716
0 -2 17 0.1648
9 0 -2 0.2239
0 2 -16 0.1692
-8 0 -1 0.2716
0 -31 -1 0.0945
0 31 1 0.0945
0 -26 9 0.1521
0 26 -9 0.1428
0 14 -15 0.1455
0 -14 15 0.1593
-1 17 14 0.1277
0 -17 -14 0.1570
0 19 13 0.1243

_exptl_crystal_size_max          0.522
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.197
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
-8.5320 0.6929 -0.2359 -0.0058 0.0271 0.9996
-0.4006 -1.9620 16.5548 -0.2072 0.9699 -0.1275
8.6245 -0.4059 -2.2075 0.0364 -0.1705 -0.9847
-0.0350 1.9847 -16.4617 0.2056 -0.9624 0.1775
-8.4924 -0.2623 -0.7391 0.0319 0.0062 0.9995
-0.1264 -31.0798 -1.0325 0.9779 0.2089 0.0007
-0.1432 31.0885 1.0097 -0.9775 -0.2088 0.0311
0.0000 -26.0000 9.0000 0.6580 0.7407 -0.1147
-0.0000 26.0000 -9.0000 -0.6580 -0.7407 0.1147
-0.0000 14.0000 -15.0000 -0.1897 -0.9821 0.1677
0.0000 -14.0000 15.0000 0.1897 0.9821 -0.1677
-1.0000 17.0000 14.0000 -0.7513 0.6633 -0.0157
0.0000 -17.0000 -14.0000 0.7527 -0.6578 0.1325
-0.0000 19.0000 13.0000 -0.7983 0.5831 -0.1205

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12912
_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         27.485
_diffrn_reflns_theta_min         1.969
_diffrn_ambient_temperature      298
_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      9.00  35.00   0.25    0.93    --    5.00  57.00  90.00  104
  2  ω     41.00  71.00   0.25    0.93    --    5.00  57.00  90.00  120
  3  ω    -50.00  24.00   0.25    0.93    --  -11.80  76.00 150.00  296
  4  ω     29.00  76.00   0.25    0.93    --  -11.80  76.00 150.00  188
  5  ω     -5.00  74.00   0.25    0.93    --  -11.80  76.00-120.00  316
  6  ω    -53.00  -9.00   0.25    0.93    --  -11.80  76.00-120.00  176
;
_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      -0.0013850000
_diffrn_orient_matrix_UB_12      -0.0309209000
_diffrn_orient_matrix_UB_13      -0.0162152000
_diffrn_orient_matrix_UB_21      -0.0054687000
_diffrn_orient_matrix_UB_22      -0.0086081000
_diffrn_orient_matrix_UB_23      0.0574374000
_diffrn_orient_matrix_UB_31      -0.1168073000
_diffrn_orient_matrix_UB_32      0.0007999000
_diffrn_orient_matrix_UB_33      -0.0104356000
_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                2663
_reflns_number_total             3607
_reflns_odcompleteness_completeness 99.60
_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         0.432
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.101
_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)+(0.0736P)²+0.2798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1503
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00N(H00N)
2.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00P(H00C,H00D), C00Q(H00F,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00G(H00G), C00I(H00I), C00K(H00K)
;
_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
F001 F 0.40864(18) 0.36512(5) 0.36843(10) 0.0659(3) Uani 1 1 d . . . . .
F002 F 1.22069(18) 0.28400(5) 0.53573(11) 0.0676(3) Uani 1 1 d . . . . .
F003 F 1.0130(2) 0.36077(5) 0.65928(10) 0.0686(3) Uani 1 1 d . . . . .
F004 F 0.6201(2) 0.28911(5) 0.24398(10) 0.0703(3) Uani 1 1 d . . . . .
O7 O -0.0155(2) 0.60704(6) 0.83883(11) 0.0627(4) Uani 1 1 d . . . . .
O006 O -0.2838(3) 0.65093(9) 1.01584(17) 0.0926(6) Uani 1 1 d . . . . .
C007 C 0.7055(3) 0.36625(7) 0.51675(14) 0.0472(4) Uani 1 1 d . . . . .
C008 C 0.3788(3) 0.48732(7) 0.68803(14) 0.0465(4) Uani 1 1 d . . . . .
C009 C 0.1246(3) 0.56834(7) 0.79492(14) 0.0474(4) Uani 1 1 d . . . . .
C00A C 0.9253(3) 0.28531(7) 0.38696(15) 0.0483(4) Uani 1 1 d . . . . .
C00B C 0.6098(3) 0.34606(7) 0.41019(15) 0.0479(4) Uani 1 1 d . . . . .
C00C C 0.7173(3) 0.30687(7) 0.34643(14) 0.0482(4) Uani 1 1 d . . . . .
C00D C 1.0209(3) 0.30425(7) 0.49383(16) 0.0487(4) Uani 1 1 d . . . . .
C00E C 0.1594(3) 0.49801(8) 0.64503(14) 0.0496(4) Uani 1 1 d . . . . .
H00E H 0.096914 0.477646 0.579733 0.059 Uiso 1 1 calc R U . . .
C00F C 0.9137(3) 0.34359(7) 0.55754(15) 0.0486(4) Uani 1 1 d . . . . .
C00G C 0.0339(3) 0.53798(8) 0.69719(14) 0.0496(4) Uani 1 1 d . . . . .
H00G H -0.112232 0.544763 0.667054 0.060 Uiso 1 1 calc R U . . .
C10 C 0.5036(3) 0.44484(8) 0.63147(16) 0.0523(4) Uani 1 1 d . . . . .
C00I C 0.4685(3) 0.51858(8) 0.78490(17) 0.0558(4) Uani 1 1 d . . . . .
H00I H 0.615309 0.512304 0.814268 0.067 Uiso 1 1 calc R U . . .
C00J C 0.5971(3) 0.40874(8) 0.58095(16) 0.0542(4) Uani 1 1 d . . . . .
C00K C 0.3434(3) 0.55893(8) 0.83865(17) 0.0574(5) Uani 1 1 d . . . . .
H00K H 0.405645 0.579602 0.903635 0.069 Uiso 1 1 calc R U . . .
C00L C 1.0401(3) 0.24460(9) 0.32104(17) 0.0612(5) Uani 1 1 d . . . . .
N00M N 1.1356(4) 0.21331(9) 0.26930(19) 0.0888(6) Uani 1 1 d . . . . .
C00N C 0.0530(4) 0.63681(8) 0.94500(18) 0.0627(5) Uani 1 1 d . . . . .
H00N H 0.195999 0.656833 0.945611 0.075 Uiso 1 1 calc R U . . .
C00O C -0.1276(4) 0.68134(10) 0.9609(2) 0.0811(7) Uani 1 1 d . . . . .
H00A H -0.067659 0.715384 1.006743 0.097 Uiso 1 1 calc R U . . .
H00B H -0.194988 0.696478 0.887348 0.097 Uiso 1 1 calc R U . . .
C00P C 0.0509(5) 0.59461(11) 1.04555(19) 0.0821(7) Uani 1 1 d . . . . .
H00C H 0.085241 0.553466 1.025265 0.099 Uiso 1 1 calc R U . . .
H00D H 0.155860 0.607534 1.109815 0.099 Uiso 1 1 calc R U . . .
C00Q C -0.1771(5) 0.59923(19) 1.0723(2) 0.1169(12) Uani 1 1 d . . . . .
H00F H -0.257970 0.562795 1.047404 0.140 Uiso 1 1 calc R U . . .
H00H H -0.175903 0.603084 1.154269 0.140 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
F001 C00B 1.3327(19) . ?
F002 C00D 1.334(2) . ?
F003 C00F 1.328(2) . ?
F004 C00C 1.335(2) . ?
O7 C009 1.361(2) . ?
O7 C00N 1.429(2) . ?
O006 C00O 1.396(3) . ?
O006 C00Q 1.435(4) . ?
C007 C00B 1.389(2) . ?
C007 C00F 1.394(2) . ?
C007 C00J 1.424(2) . ?
C008 C00E 1.392(2) . ?
C008 C10 1.430(2) . ?
C008 C00I 1.386(3) . ?
C009 C00G 1.386(2) . ?
C009 C00K 1.386(3) . ?
C00A C00C 1.384(3) . ?
C00A C00D 1.384(3) . ?
C00A C00L 1.433(2) . ?
C00B C00C 1.371(2) . ?
C00D C00F 1.372(2) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.369(2) . ?
C00G H00G 0.9300 . ?
C10 C00J 1.187(2) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.383(2) . ?
C00K H00K 0.9300 . ?
C00L N00M 1.134(2) . ?
C00N H00N 0.9800 . ?
C00N C00O 1.510(3) . ?
C00N C00P 1.511(3) . ?
C00O H00A 0.9700 . ?
C00O H00B 0.9700 . ?
C00P H00C 0.9700 . ?
C00P H00D 0.9700 . ?
C00P C00Q 1.475(4) . ?
C00Q H00F 0.9700 . ?
C00Q H00H 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C009 O7 C00N 119.76(15) . . ?
C00O O006 C00Q 107.5(2) . . ?
C00B C007 C00F 117.04(15) . . ?
C00B C007 C00J 121.53(16) . . ?
C00F C007 C00J 121.43(16) . . ?
C00E C008 C10 119.36(16) . . ?
C00I C008 C00E 118.31(15) . . ?
C00I C008 C10 122.33(16) . . ?
O7 C009 C00G 114.67(15) . . ?
O7 C009 C00K 125.38(16) . . ?
C00G C009 C00K 119.94(15) . . ?
C00C C00A C00L 121.52(17) . . ?
C00D C00A C00C 118.04(15) . . ?
C00D C00A C00L 120.44(17) . . ?
F001 C00B C007 119.49(15) . . ?
F001 C00B C00C 118.90(16) . . ?
C00C C00B C007 121.61(16) . . ?
F004 C00C C00A 119.47(15) . . ?
F004 C00C C00B 119.62(16) . . ?
C00B C00C C00A 120.91(16) . . ?
F002 C00D C00A 119.55(15) . . ?
F002 C00D C00F 119.37(17) . . ?
C00F C00D C00A 121.07(16) . . ?
C008 C00E H00E 119.4 . . ?
C00G C00E C008 121.14(15) . . ?
C00G C00E H00E 119.4 . . ?
F003 C00F C007 119.89(15) . . ?
F003 C00F C00D 118.80(16) . . ?
C00D C00F C007 121.30(16) . . ?
C009 C00G H00G 120.0 . . ?
C00E C00G C009 119.98(16) . . ?
C00E C00G H00G 120.0 . . ?
C00J C10 C008 176.5(2) . . ?
C008 C00I H00I 119.4 . . ?
C00K C00I C008 121.15(17) . . ?
C00K C00I H00I 119.4 . . ?
C10 C00J C007 178.0(2) . . ?
C009 C00K H00K 120.3 . . ?
C00I C00K C009 119.47(17) . . ?
C00I C00K H00K 120.3 . . ?
N00M C00L C00A 178.2(2) . . ?
O7 C00N H00N 111.9 . . ?
O7 C00N C00O 105.90(19) . . ?
O7 C00N C00P 111.93(16) . . ?
C00O C00N H00N 111.9 . . ?
C00O C00N C00P 102.85(19) . . ?
C00P C00N H00N 111.9 . . ?
O006 C00O C00N 107.54(18) . . ?
O006 C00O H00A 110.2 . . ?
O006 C00O H00B 110.2 . . ?
C00N C00O H00A 110.2 . . ?
C00N C00O H00B 110.2 . . ?
H00A C00O H00B 108.5 . . ?
C00N C00P H00C 111.1 . . ?
C00N C00P H00D 111.1 . . ?
H00C C00P H00D 109.0 . . ?
C00Q C00P C00N 103.4(2) . . ?
C00Q C00P H00C 111.1 . . ?
C00Q C00P H00D 111.1 . . ?
O006 C00Q C00P 109.9(2) . . ?
O006 C00Q H00F 109.7 . . ?
O006 C00Q H00H 109.7 . . ?
C00P C00Q H00F 109.7 . . ?
C00P C00Q H00H 109.7 . . ?
H00F C00Q H00H 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C00B C00C F004 0.6(2) . . . . ?
F001 C00B C00C C00A -179.20(14) . . . . ?
F002 C00D C00F F003 0.4(2) . . . . ?
F002 C00D C00F C007 179.49(14) . . . . ?
O7 C009 C00G C00E 179.75(15) . . . . ?
O7 C009 C00K C00I -179.40(17) . . . . ?
O7 C00N C00O O006 87.7(2) . . . . ?
O7 C00N C00P C00Q -87.3(3) . . . . ?
C007 C00B C00C F004 -179.33(14) . . . . ?
C007 C00B C00C C00A 0.8(2) . . . . ?
C008 C00E C00G C009 -0.4(3) . . . . ?
C008 C00I C00K C009 0.0(3) . . . . ?
C009 O7 C00N C00O 173.23(15) . . . . ?
C009 O7 C00N C00P -75.4(2) . . . . ?
C00A C00D C00F F003 -179.52(14) . . . . ?
C00A C00D C00F C007 -0.5(3) . . . . ?
C00B C007 C00F F003 -179.43(14) . . . . ?
C00B C007 C00F C00D 1.5(2) . . . . ?
C00C C00A C00D F002 179.57(14) . . . . ?
C00C C00A C00D C00F -0.5(2) . . . . ?
C00D C00A C00C F004 -179.55(14) . . . . ?
C00D C00A C00C C00B 0.3(2) . . . . ?
C00E C008 C00I C00K 0.7(3) . . . . ?
C00F C007 C00B F001 178.32(14) . . . . ?
C00F C007 C00B C00C -1.7(2) . . . . ?
C00G C009 C00K C00I -0.8(3) . . . . ?
C10 C008 C00E C00G 179.51(16) . . . . ?
C10 C008 C00I C00K -179.30(17) . . . . ?
C00I C008 C00E C00G -0.5(2) . . . . ?
C00J C007 C00B F001 -2.4(2) . . . . ?
C00J C007 C00B C00C 177.57(15) . . . . ?
C00J C007 C00F F003 1.3(2) . . . . ?
C00J C007 C00F C00D -177.75(16) . . . . ?
C00K C009 C00G C00E 1.1(3) . . . . ?
C00L C00A C00C F004 0.5(2) . . . . ?
C00L C00A C00C C00B -179.67(16) . . . . ?
C00L C00A C00D F002 -0.5(2) . . . . ?
C00L C00A C00D C00F 179.49(16) . . . . ?
C00N O7 C009 C00G 174.42(15) . . . . ?
C00N O7 C009 C00K -7.0(3) . . . . ?
C00N C00P C00Q O006 -14.7(3) . . . . ?
C00O O006 C00Q C00P -3.9(3) . . . . ?
C00O C00N C00P C00Q 26.0(3) . . . . ?
C00P C00N C00O O006 -29.9(3) . . . . ?
C00Q O006 C00O C00N 21.3(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 1.336
_oxdiff_exptl_absorpt_empirical_full_min 0.636
