# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_7072-9921_avv873
_database_code_depnum_ccdc_archive 'CCDC 1875102'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F3'
_chemical_formula_sum            'C23 H19 F3'
_chemical_formula_weight         352.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.7304(4)
_cell_length_b                   18.6098(5)
_cell_length_c                   9.9301(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.595(4)
_cell_angle_gamma                90
_cell_volume                     1788.36(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6880
_cell_measurement_theta_min      4.6050
_shelx_estimated_absorpt_T_max   0.784
_shelx_estimated_absorpt_T_min   0.710
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19190
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.993
_diffrn_reflns_theta_min         4.569
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -63.00   0.50    0.20    --  -41.35 -48.00 -32.00   78
  2  ω    -47.00  -9.00   0.50    0.20    --  -41.35  48.00 115.00   76
  3  ω    -56.00 -26.00   0.50    0.20    --  -41.35 -48.00 -32.00   60
  4  ω     51.00  78.00   0.50    0.20    --   41.35  48.00 115.00   54
  5  ω     38.00 105.00   0.50    0.66    --  101.00 -48.00 -32.00  134
  6  ω     91.00 154.00   0.50    0.66    --  101.00  48.00 115.00  126
  7  ω    -53.00  19.00   0.50    0.20    --  -41.35  43.00 -60.00  144
  8  ω    -61.00 -34.00   0.50    0.20    --  -41.35  11.00-120.00   54
  9  ω   -101.00 -25.00   0.50    0.20    --  -41.35 -65.00  90.00  152
 10  ω    -24.00   3.00   0.50    0.20    --  -41.35  11.00-120.00   54
 11  ω     56.00 106.00   0.50    0.20    --   41.35  32.00 -90.00  100
 12  ω     35.00  66.00   0.50    0.20    --   41.35  32.00   0.00   62
 13  ω     71.00  99.00   0.50    0.20    --   41.35  65.00-150.00   56
 14  ω     70.00  97.00   0.50    0.20    --   41.35  32.00   0.00   54
 15  ω     25.00  67.00   0.50    0.20    --   41.35  65.00-150.00   84
 16  ω     29.00  99.00   0.50    0.20    --   41.35  43.00-150.00  140
 17  ω      4.00  43.00   0.50    0.20    --   41.35 -48.00 -32.00   78
 18  ω     35.00 106.00   0.50    0.66    --  101.00 -25.00  90.00  142
 19  ω     51.00 109.00   0.50    0.66    --  101.00 -33.00 150.00  116
 20  ω     79.00 106.00   0.50    0.66    --  101.00 -25.00 -90.00   54
 21  ω     89.00 141.00   0.50    0.66    --  101.00  42.00  60.00  104
 22  ω     88.00 154.00   0.50    0.66    --  101.00  50.00  90.00  132
 23  ω     35.00  77.00   0.50    0.66    --  101.00 -25.00 -90.00   84
 24  ω     61.00 127.00   0.50    0.66    --  101.00 -77.00 120.00  132
 25  ω    109.00 149.00   0.50    0.66    --  101.00 133.00 -30.00   80
 26  ω     93.00 157.00   0.50    0.66    --  101.00  25.00  30.00  128
 27  ω     95.00 151.00   0.50    0.66    --  101.00  17.00 -90.00  112
 28  ω     59.00  96.00   0.50    0.66    --  101.00 -50.00-180.00   74
 29  ω     57.00  85.00   0.50    0.66    --  101.00 -33.00-120.00   56
 30  ω     50.00 112.00   0.50    0.66    --  101.00 -50.00  90.00  124
 31  ω    111.00 148.00   0.50    0.66    --  101.00  33.00-180.00   74
 32  ω   -103.00 -76.00   0.50    0.20    --  -41.35 -48.00 -32.00   54
 33  ω    -59.00 -24.00   0.50    0.20    --  -41.35 -54.00-180.00   70
 34  ω      3.00  28.00   0.50    0.20    --  -41.35  21.00 -90.00   50
 35  ω    -37.00 -10.00   0.50    0.20    --  -41.35  21.00 -90.00   54
 36  ω     32.00  57.00   0.50    0.20    --   41.35  54.00 -90.00   50
 37  ω     67.00  96.00   0.50    0.20    --   41.35  54.00 -90.00   58
 38  ω     37.00  64.00   0.50    0.20    --   41.35  32.00-180.00   54
 39  ω     51.00  94.00   0.50    0.20    --   41.35-138.00  30.00   86
 40  ω     17.00  42.00   0.50    0.20    --   41.35  77.00-120.00   50
 41  ω     82.00 107.00   0.50    0.20    --   41.35  32.00-180.00   50
 42  ω    131.00 157.00   0.50    0.66    --  101.00  77.00-120.00   52
 43  ω     82.00 119.00   0.50    0.66    --  101.00  -8.00 120.00   74
 44  ω     77.00 102.00   0.50    0.66    --  101.00  77.00-120.00   50
 45  ω     80.00 110.00   0.50    0.66    --  101.00  68.00-120.00   60
 46  ω     86.00 111.00   0.50    0.66    --  101.00  50.00-180.00   50
 47  ω     84.00 115.00   0.50    0.66    --  101.00  59.00 150.00   62
 48  ω     29.00  56.00   0.50    0.66    --  101.00  -8.00 120.00   54
 49  ω     96.00 150.00   0.50    0.66    --  101.00  33.00 150.00  108
 50  ω    132.00 157.00   0.50    0.66    --  101.00  77.00-150.00   50
 51  ω    122.00 149.00   0.50    0.66    --  101.00  73.00 177.21   54
 52  ω     76.00 103.00   0.50    0.66    --  101.00  77.00-180.00   54
 53  ω     83.00 109.00   0.50    0.66    --  101.00  59.00-120.00   52
 54  ω     83.00 109.00   0.50    0.66    --  101.00  59.00-180.00   52
 55  ω     83.00 110.00   0.50    0.66    --  101.00  59.00 -90.00   54
 56  ω    124.00 151.00   0.50    0.66    --  101.00  77.00 150.00   54
 57  ω     76.00 112.00   0.50    0.66    --  101.00  77.00 150.00   72
 58  ω     76.00 102.00   0.50    0.66    --  101.00  77.00-150.00   52
 59  ω     41.00  97.00   0.50    0.66    --  101.00 -68.00 -60.00  112
 60  ω    131.00 157.00   0.50    0.66    --  101.00  50.00  60.00   52
 61  ω     89.00 116.00   0.50    0.66    --  101.00  50.00 -90.00   54
 62  ω    131.00 157.00   0.50    0.66    --  101.00  50.00-180.00   52
 63  ω     47.00 109.00   0.50    0.66    --  101.00 -25.00 -30.00  124
 64  ω     80.00 137.00   0.50    0.66    --  101.00  68.00 -90.00  114
 65  ω     78.00 104.00   0.50    0.66    --  101.00  73.00 177.21   52
 66  ω    132.00 157.00   0.50    0.66    --  101.00  59.00-150.00   50
 67  ω     37.00  62.00   0.50    0.66    --  101.00 -33.00 -60.00   50
 68  ω     81.00 110.00   0.50    0.66    --  101.00  63.00-132.73   58
 69  ω     80.00 110.00   0.50    0.66    --  101.00  68.00-150.00   60
 70  ω    113.00 140.00   0.50    0.66    --  101.00  33.00  30.00   54
 71  ω     86.00 142.00   0.50    0.66    --  101.00  50.00-150.00  112
 72  ω     84.00 111.00   0.50    0.66    --  101.00  59.00-150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1124788000
_diffrn_orient_matrix_UB_12      -0.0365074000
_diffrn_orient_matrix_UB_13      -0.0332876000
_diffrn_orient_matrix_UB_21      -0.1123546000
_diffrn_orient_matrix_UB_22      -0.0323221000
_diffrn_orient_matrix_UB_23      -0.1441108000
_diffrn_orient_matrix_UB_31      0.0069985000
_diffrn_orient_matrix_UB_32      0.0669476000
_diffrn_orient_matrix_UB_33      -0.0878368000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2977
_reflns_number_total             3388
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.041
_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)+(0.0620P)²+0.4831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1107
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C9(H9), C13(H13), C18(H18), C20(H20), C14(H14), C21(H21), C8(H8),
 C15(H15), C16(H16), C6(H6), C22(H22), C12(H12)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F3 F 0.52584(8) 0.12439(5) 0.26132(9) 0.0333(2) Uani 1 1 d . . . . .
F1 F 0.41688(9) 0.17862(5) 0.05080(9) 0.0358(2) Uani 1 1 d . . . . .
F2 F 0.41990(8) 0.22426(4) 0.25177(10) 0.0343(2) Uani 1 1 d . . . . .
C2 C 0.27871(13) 0.12015(7) 0.15332(15) 0.0262(3) Uani 1 1 d . . . . .
C1 C 0.41003(14) 0.16176(8) 0.17920(15) 0.0289(3) Uani 1 1 d . . . . .
C4 C 0.03681(13) 0.11654(7) -0.04035(15) 0.0260(3) Uani 1 1 d . . . . .
H4 H -0.0119 0.0962 0.0171 0.031 Uiso 1 1 calc R . . . .
C11 C 0.28525(13) 0.09674(8) 0.30532(15) 0.0270(3) Uani 1 1 d . . . . .
C7 C 0.16972(14) -0.04798(7) -0.17754(16) 0.0285(3) Uani 1 1 d . . . . .
C19 C -0.12973(16) 0.21284(8) -0.41509(16) 0.0333(3) Uani 1 1 d . . . . .
H19 H -0.1029 0.2317 -0.4875 0.040 Uiso 1 1 calc R . . . .
C9 C 0.35016(14) 0.00529(8) 0.04564(16) 0.0284(3) Uani 1 1 d . . . . .
H9 H 0.4428 0.0053 0.1204 0.034 Uiso 1 1 calc R . . . .
C13 C 0.30766(15) 0.00409(9) 0.48613(17) 0.0344(3) Uani 1 1 d . . . . .
H13 H 0.3195 -0.0452 0.5140 0.041 Uiso 1 1 calc R . . . .
C18 C -0.03287(14) 0.17928(8) -0.28825(16) 0.0300(3) Uani 1 1 d . . . . .
H18 H 0.0600 0.1751 -0.2750 0.036 Uiso 1 1 calc R . . . .
C20 C -0.26638(16) 0.21884(8) -0.43626(17) 0.0356(3) Uani 1 1 d . . . . .
H20 H -0.3327 0.2421 -0.5226 0.043 Uiso 1 1 calc R . . . .
C3 C 0.15030(13) 0.16839(7) 0.06290(15) 0.0276(3) Uani 1 1 d . . . . .
H3A H 0.1197 0.1938 0.1310 0.033 Uiso 1 1 calc R . . . .
H3B H 0.1726 0.2045 0.0034 0.033 Uiso 1 1 calc R . . . .
C17 C -0.06954(13) 0.15162(7) -0.18024(15) 0.0256(3) Uani 1 1 d . . . . .
C14 C 0.29452(16) 0.05458(9) 0.58127(17) 0.0369(4) Uani 1 1 d . . . . .
H14 H 0.2971 0.0403 0.6743 0.044 Uiso 1 1 calc R . . . .
C21 C -0.30504(15) 0.19072(8) -0.33104(17) 0.0344(3) Uani 1 1 d . . . . .
H21 H -0.3984 0.1943 -0.3457 0.041 Uiso 1 1 calc R . . . .
C8 C 0.30519(14) -0.04714(8) -0.06481(16) 0.0293(3) Uani 1 1 d . . . . .
H8 H 0.3680 -0.0834 -0.0638 0.035 Uiso 1 1 calc R . . . .
C5 C 0.12144(13) 0.05705(7) -0.06510(15) 0.0249(3) Uani 1 1 d . . . . .
C15 C 0.27739(17) 0.12654(9) 0.53927(17) 0.0375(4) Uani 1 1 d . . . . .
H15 H 0.2687 0.1616 0.6042 0.045 Uiso 1 1 calc R . . . .
C16 C 0.27287(15) 0.14743(8) 0.40306(16) 0.0329(3) Uani 1 1 d . . . . .
H16 H 0.2612 0.1968 0.3758 0.039 Uiso 1 1 calc R . . . .
C6 C 0.07784(14) 0.00509(7) -0.17635(15) 0.0270(3) Uani 1 1 d . . . . .
H6 H -0.0145 0.0056 -0.2518 0.032 Uiso 1 1 calc R . . . .
C22 C -0.20738(14) 0.15714(8) -0.20328(16) 0.0290(3) Uani 1 1 d . . . . .
H22 H -0.2347 0.1379 -0.1315 0.035 Uiso 1 1 calc R . . . .
C10 C 0.25737(13) 0.05801(7) 0.04527(15) 0.0257(3) Uani 1 1 d . . . . .
C12 C 0.30364(14) 0.02502(8) 0.34949(16) 0.0294(3) Uani 1 1 d . . . . .
H12 H 0.3136 -0.0102 0.2856 0.035 Uiso 1 1 calc R . . . .
C23 C 0.12360(16) -0.10503(9) -0.29740(17) 0.0359(3) Uani 1 1 d . . . . .
H23A H 0.2041 -0.1322 -0.2912 0.054 Uiso 1 1 calc GR . . . .
H23B H 0.0780 -0.0822 -0.3957 0.054 Uiso 1 1 calc GR . . . .
H23C H 0.0587 -0.1377 -0.2831 0.054 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
F3 C1 1.3480(16) . ?
F1 C1 1.3456(17) . ?
F2 C1 1.3482(17) . ?
C2 C1 1.5291(19) . ?
C2 C11 1.5432(19) . ?
C2 C3 1.5626(18) . ?
C2 C10 1.5260(19) . ?
C4 C3 1.5449(18) . ?
C4 C17 1.5128(18) . ?
C4 C5 1.5177(19) . ?
C11 C16 1.400(2) . ?
C11 C12 1.392(2) . ?
C7 C8 1.400(2) . ?
C7 C6 1.399(2) . ?
C7 C23 1.510(2) . ?
C19 C18 1.388(2) . ?
C19 C20 1.393(2) . ?
C9 C8 1.390(2) . ?
C9 C10 1.3968(19) . ?
C13 C14 1.382(2) . ?
C13 C12 1.394(2) . ?
C18 C17 1.391(2) . ?
C20 C21 1.383(2) . ?
C17 C22 1.3993(19) . ?
C14 C15 1.391(2) . ?
C21 C22 1.396(2) . ?
C5 C6 1.388(2) . ?
C5 C10 1.3956(18) . ?
C15 C16 1.388(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C2 C11 109.23(11) . . ?
C1 C2 C3 109.00(11) . . ?
C11 C2 C3 112.36(11) . . ?
C10 C2 C1 110.45(11) . . ?
C10 C2 C11 113.78(11) . . ?
C10 C2 C3 101.78(10) . . ?
F3 C1 F2 106.42(11) . . ?
F3 C1 C2 112.47(11) . . ?
F1 C1 F3 106.26(11) . . ?
F1 C1 F2 106.34(11) . . ?
F1 C1 C2 112.48(11) . . ?
F2 C1 C2 112.37(12) . . ?
C17 C4 C3 113.92(11) . . ?
C17 C4 C5 115.65(11) . . ?
C5 C4 C3 101.99(10) . . ?
C16 C11 C2 120.65(13) . . ?
C12 C11 C2 121.28(13) . . ?
C12 C11 C16 118.07(13) . . ?
C8 C7 C23 120.77(13) . . ?
C6 C7 C8 118.51(13) . . ?
C6 C7 C23 120.72(13) . . ?
C18 C19 C20 119.99(14) . . ?
C8 C9 C10 119.15(12) . . ?
C14 C13 C12 120.39(14) . . ?
C19 C18 C17 121.07(13) . . ?
C21 C20 C19 119.70(13) . . ?
C4 C3 C2 105.61(11) . . ?
C18 C17 C4 121.02(12) . . ?
C18 C17 C22 118.55(12) . . ?
C22 C17 C4 120.43(13) . . ?
C13 C14 C15 119.26(14) . . ?
C20 C21 C22 120.24(14) . . ?
C9 C8 C7 121.70(13) . . ?
C6 C5 C4 128.12(12) . . ?
C6 C5 C10 120.82(12) . . ?
C10 C5 C4 111.03(12) . . ?
C16 C15 C14 120.42(15) . . ?
C15 C16 C11 120.85(14) . . ?
C5 C6 C7 120.12(12) . . ?
C21 C22 C17 120.45(14) . . ?
C9 C10 C2 129.80(12) . . ?
C5 C10 C2 110.51(12) . . ?
C5 C10 C9 119.67(13) . . ?
C11 C12 C13 120.99(14) . . ?

_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 1.153
_oxdiff_exptl_absorpt_empirical_full_min 0.886
####################################################################### 
# 
# 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_7072-9949_emt079_prism
_database_code_depnum_ccdc_archive 'CCDC 1875109'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 F3 O2'
_chemical_formula_sum            'C24 H21 F3 O2'
_chemical_formula_weight         398.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.28774(13)
_cell_length_b                   13.98378(18)
_cell_length_c                   16.25245(18)
_cell_angle_alpha                94.5890(10)
_cell_angle_beta                 106.2794(11)
_cell_angle_gamma                98.2135(11)
_cell_volume                     1989.34(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    33355
_cell_measurement_temperature    100(5)
_cell_measurement_theta_max      71.9530
_cell_measurement_theta_min      2.7880
_shelx_estimated_absorpt_T_max   0.789
_shelx_estimated_absorpt_T_min   0.664
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41358
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.116
_diffrn_reflns_theta_min         2.855
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  17.00   0.50    0.20    --   41.35 -84.00-120.00   74
  2  ω     25.00  68.00   0.50    0.20    --   41.35 -84.00-120.00   86
  3  ω     37.00 106.00   0.50    0.80    --  101.00 -84.00-120.00  138
  4  ω     78.00 109.00   0.50    0.80    --  101.00  84.00   0.00   62
  5  ω     -2.00  26.00   0.50    0.20    --  -41.35  21.00   0.00   56
  6  ω    -68.00 -42.00   0.50    0.20    --  -41.35  84.00   0.00   52
  7  ω    -49.00 -14.00   0.50    0.20    --  -41.35  21.00   0.00   70
  8  ω    -58.00  -4.00   0.50    0.20    --  -41.35  54.00  60.00  108
  9  ω    -39.00   0.00   0.50    0.20    --  -41.35  32.00-120.00   78
 10  ω    -68.00 -25.00   0.50    0.20    --  -41.35 -54.00  30.00   86
 11  ω    -90.00 -52.00   0.50    0.20    --  -41.35 138.00 -30.00   76
 12  ω    -53.00  19.00   0.50    0.20    --  -41.35  43.00-180.00  144
 13  ω    -91.00 -12.00   0.50    0.20    --  -41.35 138.00-180.00  158
 14  ω    -11.00  18.00   0.50    0.20    --  -41.35  84.00   0.00   58
 15  ω   -104.00 -36.00   0.50    0.20    --  -41.35 -43.00 -60.00  136
 16  ω   -100.00 -72.00   0.50    0.20    --  -41.35 -43.00  30.00   56
 17  ω    -54.00 -10.00   0.50    0.20    --  -41.35  54.00-150.00   88
 18  ω    -65.00 -40.00   0.50    0.20    --  -41.35 -43.00  30.00   50
 19  ω    -43.00  -4.00   0.50    0.20    --  -41.35  54.00 -60.00   78
 20  ω    -26.00   8.00   0.50    0.20    --   41.35 -11.00  90.00   68
 21  ω     13.00  64.00   0.50    0.20    --   41.35 -11.00  90.00  102
 22  ω     30.00 104.00   0.50    0.20    --   41.35  54.00  90.00  148
 23  ω     24.00  69.00   0.50    0.20    --   41.35-104.00 150.00   90
 24  ω    -14.00  18.00   0.50    0.20    --   41.35-104.00 150.00   64
 25  ω     50.00  77.00   0.50    0.20    --   41.35-138.00  90.00   54
 26  ω     50.00 105.00   0.50    0.20    --   41.35  32.00-120.00  110
 27  ω     43.00 100.00   0.50    0.80    --  101.00 -77.00  90.00  114
 28  ω     40.00 106.00   0.50    0.80    --  101.00 -25.00-180.00  132
 29  ω     88.00 157.00   0.50    0.80    --  101.00  42.00  60.00  138
 30  ω     97.00 129.00   0.50    0.80    --  101.00 -87.00 -60.00   64
 31  ω     47.00  81.00   0.50    0.80    --  101.00 -87.00 -60.00   68
 32  ω     42.00  68.00   0.50    0.80    --  101.00 -33.00 -30.00   52
 33  ω     64.00 108.00   0.50    0.80    --  101.00-111.00-180.00   88
 34  ω     50.00 113.00   0.50    0.80    --  101.00-111.00  90.00  126
 35  ω     92.00 124.00   0.50    0.80    --  101.00  25.00 120.00   64
 36  ω     48.00 110.00   0.50    0.80    --  101.00-111.00-120.00  124
 37  ω     35.00  91.00   0.50    0.80    --  101.00-111.00-150.00  112
 38  ω     48.00  82.00   0.50    0.80    --  101.00 -25.00 -90.00   68
 39  ω     61.00 114.00   0.50    0.80    --  101.00-111.00 -60.00  106
 40  ω     91.00 157.00   0.50    0.80    --  101.00 111.00 -90.00  132
 41  ω     82.00 156.00   0.50    0.80    --  101.00  93.00 -60.00  148
 42  ω     72.00 113.00   0.50    0.80    --  101.00-111.00   0.00   82
 43  ω     88.00 157.00   0.50    0.80    --  101.00  93.00 -30.00  138
 44  ω     51.00  98.00   0.50    0.80    --  101.00 -68.00  30.00   94
 45  ω     40.00 101.00   0.50    0.80    --  101.00-133.00-180.00  122
 46  ω     80.00 112.00   0.50    0.80    --  101.00  68.00  90.00   64
 47  ω    127.00 156.00   0.50    0.80    --  101.00  68.00  90.00   58
 48  ω     79.00 157.00   0.50    0.80    --  101.00   8.00  60.00  156
 49  ω     39.00 120.00   0.50    0.80    --  101.00 -59.00 -60.00  162
 50  ω     69.00  95.00   0.50    0.80    --  101.00 -33.00 120.00   52
 51  ω     76.00 125.00   0.50    0.80    --  101.00  77.00 150.00   98
 52  ω     82.00 108.00   0.50    0.80    --  101.00  93.00-150.00   52
 53  ω     74.00 103.00   0.50    0.80    --  101.00 -33.00 -30.00   58
 54  ω     44.00 107.00   0.50    0.80    --  101.00 -42.00-150.00  126
 55  ω    105.00 147.00   0.50    0.80    --  101.00 111.00-120.00   84
 56  ω    122.00 157.00   0.50    0.80    --  101.00  84.00   0.00   70
 57  ω    -65.00 -39.00   0.50    0.20    --  -41.35  84.00   0.00   52
 58  ω    -39.00 -14.00   0.50    0.20    --   12.00 129.00 144.37   50
 59  ω    -28.00  -3.00   0.50    0.20    --   16.00 119.00 -24.82   50
 60  ω    -13.00  12.00   0.50    0.20    --   24.00 106.00  18.84   50
 61  ω     -3.00  22.00   0.50    0.20    --   28.00  95.00 105.95   50
 62  ω     -2.00  23.00   0.50    0.20    --   28.00  93.00 171.65   50
 63  ω     -4.00  21.00   0.50    0.20    --   28.00  97.00 -25.01   50
 64  ω     -3.00  22.00   0.50    0.20    --   28.00  95.00-114.31   50
 65  ω      4.00  29.00   0.50    0.20    --   32.00  88.00  48.53   50
 66  ω      4.00  29.00   0.50    0.20    --   32.00  88.00-135.79   50
 67  ω      9.00  34.00   0.50    0.20    --   36.00  85.00-128.61   50
 68  ω      9.00  34.00   0.50    0.20    --   36.00  85.00 -42.35   50
 69  ω      9.00  34.00   0.50    0.20    --   36.00  85.00   3.08   50
 70  ω      9.00  34.00   0.50    0.20    --   36.00  84.00  91.85   50
 71  ω      9.00  46.00   0.50    0.20    --   41.35 -32.00   0.00   74
 72  ω     18.00  43.00   0.50    0.20    --   44.00  82.00 -14.44   50
 73  ω     19.00  44.00   0.50    0.20    --   44.00  81.00 -50.11   50
 74  ω     19.00  44.00   0.50    0.20    --   44.00  81.00  39.48   50
 75  ω     18.00  43.00   0.50    0.20    --   44.00  82.00 126.77   50
 76  ω     19.00  44.00   0.50    0.20    --   44.00  80.00  86.19   50
 77  ω     19.00  44.00   0.50    0.20    --   44.00  80.00 -84.89   50
 78  ω     18.00  43.00   0.50    0.20    --   44.00  82.00 164.81   50
 79  ω     25.00  51.00   0.50    0.20    --   48.00  77.00-153.24   52
 80  ω     27.00  52.00   0.50    0.20    --   52.00  77.00 -28.60   50
 81  ω     29.00  55.00   0.50    0.20    --   52.00  75.00 107.60   52
 82  ω     87.00 116.00   0.50    0.20    --   52.00  76.00-125.48   58
 83  ω     28.00  54.00   0.50    0.20    --   52.00  77.00 -68.51   52
 84  ω     27.00  53.00   0.50    0.20    --   52.00  76.00  16.84   52
 85  ω     27.00  53.00   0.50    0.20    --   52.00  76.00-125.48   52
 86  ω     31.00  57.00   0.50    0.20    --   56.00  77.00 134.56   52
 87  ω     32.00  58.00   0.50    0.20    --   56.00  77.00 171.00   52
 88  ω     32.00  58.00   0.50    0.20    --   56.00  77.00  38.39   52
 89  ω     95.00 120.00   0.50    0.20    --   56.00  74.00-119.58   50
 90  ω     35.00  61.00   0.50    0.20    --   56.00  74.00-119.58   52
 91  ω     41.00  80.00   0.50    0.20    --   60.00  73.00-109.17   78
 92  ω     41.00  70.00   0.50    0.20    --   64.00  72.00-169.67   58
 93  ω     44.00  70.00   0.50    0.20    --   64.00  66.00 100.50   52
 94  ω     42.00  68.00   0.50    0.20    --   64.00  69.00   1.65   52
 95  ω     45.00  84.00   0.50    0.20    --   68.00  73.00 -34.35   78
 96  ω     43.00 107.00   0.50    0.20    --   68.00  77.00 140.90  128
 97  ω     83.00 119.00   0.50    0.20    --   68.00  62.00-155.76   72
 98  ω     50.00  76.00   0.50    0.20    --   68.00  62.00-155.76   52
 99  ω     47.00  96.00   0.50    0.20    --   68.00  69.00  55.53   98
100  ω     97.00 130.00   0.50    0.20    --   68.00  76.00  96.78   66
101  ω     46.00  74.00   0.50    0.20    --   68.00  76.00  96.78   56
102  ω     53.00  87.00   0.50    0.80    --   76.00  72.00 -70.28   68
103  ω     57.00  86.00   0.50    0.80    --   80.00  74.00   3.10   58
104  ω     61.00  87.00   0.50    0.80    --   84.00  73.00  69.55   52
105  ω    104.00 130.00   0.50    0.80    --   88.00  75.00 119.79   52
106  ω     64.00  89.00   0.50    0.80    --   88.00  75.00 119.79   50
107  ω     38.00  63.00   0.50    0.80    --  101.00 -33.00   0.00   50
108  ω    129.00 155.00   0.50    0.80    --  101.00  77.00  60.00   52
109  ω     76.00 112.00   0.50    0.80    --  101.00  77.00  60.00   72
110  ω     76.00 150.00   0.50    0.80    --  101.00  77.00-120.00  148
111  ω     83.00 109.00   0.50    0.80    --  101.00  59.00 -30.00   52
112  ω     76.00 102.00   0.50    0.80    --  101.00  77.00-150.00   52
113  ω     76.00 113.00   0.50    0.80    --  101.00  77.00 -30.00   74
114  ω    127.00 153.00   0.50    0.80    --  101.00  59.00 -30.00   52
115  ω     81.00 117.00   0.50    0.80    --  101.00  68.00   0.00   72
116  ω    130.00 156.00   0.50    0.80    --  101.00  59.00  90.00   52
117  ω     71.00 100.00   0.50    0.80    --  101.00 -33.00 -90.00   58
118  ω     76.00 124.00   0.50    0.80    --  101.00  77.00  90.00   96
119  ω    127.00 154.00   0.50    0.80    --  101.00  77.00  90.00   54
120  ω     83.00 109.00   0.50    0.80    --  101.00  59.00  90.00   52
121  ω     95.00 120.00   0.50    0.80    --  101.00 -59.00 120.00   50
122  ω     42.00  68.00   0.50    0.80    --  101.00 -33.00 -90.00   52
123  ω     39.00  65.00   0.50    0.80    --  101.00 -59.00 120.00   52
124  ω    129.00 155.00   0.50    0.80    --  101.00  77.00 -60.00   52
125  ω     76.00 101.00   0.50    0.80    --  101.00  77.00 -60.00   50
126  ω     83.00 145.00   0.50    0.80    --  101.00  59.00-180.00  124
127  ω    129.00 154.00   0.50    0.80    --  101.00  77.00-180.00   50
128  ω     80.00 139.00   0.50    0.80    --  101.00  68.00 120.00  118
129  ω     83.00 157.00   0.50    0.80    --  101.00  59.00-150.00  148
130  ω    111.00 149.00   0.50    0.80    --  101.00  73.00-131.98   76
131  ω     76.00 101.00   0.50    0.80    --  101.00  77.00-180.00   50
132  ω    125.00 151.00   0.50    0.80    --  101.00  77.00 120.00   52
133  ω     77.00 114.00   0.50    0.80    --  101.00  77.00 120.00   74
134  ω     77.00 134.00   0.50    0.80    --  101.00  77.00  30.00  114
135  ω     78.00 104.00   0.50    0.80    --  101.00  73.00-131.98   52
136  ω    126.00 157.00   0.50    0.80    --  101.00  68.00 150.00   62
137  ω     80.00 121.00   0.50    0.80    --  101.00  68.00 150.00   82
138  ω     76.00 137.00   0.50    0.80    --  101.00  77.00 -90.00  122
139  ω     73.00  99.00   0.50    0.80    --  101.00 -33.00   0.00   52
140  ω     84.00 121.00   0.50    0.80    --  101.00  59.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1250423000
_diffrn_orient_matrix_UB_12      -0.0123648000
_diffrn_orient_matrix_UB_13      -0.0434008000
_diffrn_orient_matrix_UB_21      0.1183338000
_diffrn_orient_matrix_UB_22      0.0671931000
_diffrn_orient_matrix_UB_23      0.0759537000
_diffrn_orient_matrix_UB_31      0.0337540000
_diffrn_orient_matrix_UB_32      -0.0890115000
_diffrn_orient_matrix_UB_33      0.0475075000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7548
_reflns_number_total             7766
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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         0.646
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+1.0736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0962
_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:
 C1(H1), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C40(H40), C5(H5), C44(H44), C11(H11), C51(H51), C52(H52), C35(H35),
 C23(H23), C37(H37), C41(H41), C15(H15), C34(H34), C6(H6), C43(H43), C14(H14),
 C12(H12), C50(H50), C19(H19), C22(H22), C48(H48), C21(H21), C49(H49), C20(H20)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C29(H29A,H29B,H29C), C46(H46A,H46B,H46C), C58(H58A,H58B,
 H58C)
;
_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
F25 F 0.52468(9) 0.13294(6) 0.70841(5) 0.03004(18) Uani 1 1 d . . . . .
F54 F 0.23045(9) 0.37104(6) 0.74292(5) 0.03047(18) Uani 1 1 d . . . . .
F55 F 0.25533(10) 0.23328(6) 0.68366(5) 0.03073(18) Uani 1 1 d . . . . .
F26 F 0.73782(10) 0.19119(6) 0.68714(5) 0.03052(19) Uani 1 1 d . . . . .
F56 F 0.04771(9) 0.29052(6) 0.63638(5) 0.03113(19) Uani 1 1 d . . . . .
F27 F 0.64807(10) 0.03728(6) 0.65573(5) 0.0333(2) Uani 1 1 d . . . . .
O16 O 0.54691(11) -0.41349(7) 0.95204(6) 0.0267(2) Uani 1 1 d . . . . .
O28 O 1.25880(11) -0.09303(7) 0.83685(6) 0.0279(2) Uani 1 1 d . . . . .
O45 O 0.27572(12) 0.93259(7) 0.61364(6) 0.0298(2) Uani 1 1 d . . . . .
O57 O 0.86821(11) 0.57963(8) 0.72081(7) 0.0356(2) Uani 1 1 d . . . . .
C38 C 0.46366(14) 0.50551(9) 0.61800(8) 0.0201(3) Uani 1 1 d . . . . .
C4 C 0.89279(14) 0.05371(9) 0.80588(8) 0.0205(3) Uani 1 1 d . . . . .
C8 C 1.02381(14) -0.07283(9) 0.87052(8) 0.0205(2) Uani 1 1 d . . . . .
H8 H 1.0299 -0.1237 0.9062 0.025 Uiso 1 1 calc R . . . .
C9 C 0.90458(14) -0.01990(9) 0.85850(8) 0.0196(2) Uani 1 1 d . . . . .
C33 C 0.43407(14) 0.41391(9) 0.64401(8) 0.0202(3) Uani 1 1 d . . . . .
C7 C 1.13362(15) -0.04886(9) 0.82866(8) 0.0218(3) Uani 1 1 d . . . . .
C40 C 0.32744(15) 0.68726(10) 0.65385(8) 0.0236(3) Uani 1 1 d . . . . .
H40 H 0.3495 0.6527 0.7026 0.028 Uiso 1 1 calc R . . . .
C32 C 0.26643(14) 0.36828(9) 0.60256(8) 0.0208(3) Uani 1 1 d . . . . .
C39 C 0.30440(14) 0.63795(9) 0.57116(8) 0.0205(3) Uani 1 1 d . . . . .
C5 C 1.00291(15) 0.07680(9) 0.76347(8) 0.0232(3) Uani 1 1 d . . . . .
H5 H 0.9958 0.1272 0.7273 0.028 Uiso 1 1 calc R . . . .
C36 C 0.72743(15) 0.52152(10) 0.69827(8) 0.0233(3) Uani 1 1 d . . . . .
C44 C 0.27075(14) 0.69077(10) 0.50143(8) 0.0217(3) Uani 1 1 d . . . . .
H44 H 0.2549 0.6590 0.4449 0.026 Uiso 1 1 calc R . . . .
C11 C 0.70665(15) -0.15564(10) 0.99285(8) 0.0228(3) Uani 1 1 d . . . . .
H11 H 0.7375 -0.1054 1.0403 0.027 Uiso 1 1 calc R . . . .
C18 C 0.78911(15) 0.19576(9) 0.86592(8) 0.0216(3) Uani 1 1 d . . . . .
C51 C 0.33633(15) 0.18402(9) 0.43527(9) 0.0241(3) Uani 1 1 d . . . . .
H51 H 0.4178 0.1534 0.4281 0.029 Uiso 1 1 calc R . . . .
C47 C 0.24189(15) 0.29614(9) 0.52048(8) 0.0213(3) Uani 1 1 d . . . . .
C13 C 0.60509(14) -0.32352(9) 0.93566(8) 0.0212(3) Uani 1 1 d . . . . .
C1 C 0.77545(14) -0.03114(9) 0.89907(8) 0.0208(3) Uani 1 1 d . . . . .
H1 H 0.8107 0.0100 0.9566 0.025 Uiso 1 1 calc R . . . .
C52 C 0.35902(15) 0.24994(9) 0.50855(8) 0.0219(3) Uani 1 1 d . . . . .
H52 H 0.4558 0.2635 0.5510 0.026 Uiso 1 1 calc R . . . .
C31 C 0.19485(14) 0.46077(9) 0.58188(8) 0.0226(3) Uani 1 1 d . . . . .
H31A H 0.1012 0.4448 0.5322 0.027 Uiso 1 1 calc R . . . .
H31B H 0.1693 0.4898 0.6324 0.027 Uiso 1 1 calc R . . . .
C53 C 0.20042(15) 0.31583(10) 0.66585(9) 0.0240(3) Uani 1 1 d . . . . .
C35 C 0.69843(15) 0.43064(10) 0.72570(8) 0.0237(3) Uani 1 1 d . . . . .
H35 H 0.7788 0.4056 0.7630 0.028 Uiso 1 1 calc R . . . .
C23 C 0.67301(16) 0.23704(10) 0.88682(9) 0.0250(3) Uani 1 1 d . . . . .
H23 H 0.5704 0.2048 0.8638 0.030 Uiso 1 1 calc R . . . .
C2 C 0.65600(15) 0.01667(9) 0.83697(9) 0.0236(3) Uani 1 1 d . . . . .
H2A H 0.5897 0.0442 0.8674 0.028 Uiso 1 1 calc R . . . .
H2B H 0.5917 -0.0313 0.7877 0.028 Uiso 1 1 calc R . . . .
C37 C 0.60925(15) 0.56024(10) 0.64432(8) 0.0221(3) Uani 1 1 d . . . . .
H37 H 0.6286 0.6225 0.6263 0.027 Uiso 1 1 calc R . . . .
C10 C 0.71853(14) -0.13388(9) 0.91228(8) 0.0204(2) Uani 1 1 d . . . . .
C41 C 0.31861(15) 0.78496(10) 0.66574(8) 0.0233(3) Uani 1 1 d . . . . .
H41 H 0.3362 0.8170 0.7223 0.028 Uiso 1 1 calc R . . . .
C42 C 0.28394(15) 0.83666(9) 0.59468(9) 0.0228(3) Uani 1 1 d . . . . .
C24 C 0.66579(16) 0.11499(10) 0.71444(9) 0.0254(3) Uani 1 1 d . . . . .
C15 C 0.67636(15) -0.20985(10) 0.84454(8) 0.0229(3) Uani 1 1 d . . . . .
H15 H 0.6861 -0.1969 0.7897 0.027 Uiso 1 1 calc R . . . .
C34 C 0.55128(15) 0.37656(10) 0.69830(8) 0.0226(3) Uani 1 1 d . . . . .
H34 H 0.5313 0.3145 0.7167 0.027 Uiso 1 1 calc R . . . .
C6 C 1.12271(15) 0.02507(10) 0.77495(8) 0.0237(3) Uani 1 1 d . . . . .
H6 H 1.1977 0.0399 0.7462 0.028 Uiso 1 1 calc R . . . .
C43 C 0.25955(15) 0.78935(10) 0.51210(8) 0.0232(3) Uani 1 1 d . . . . .
H43 H 0.2355 0.8238 0.4633 0.028 Uiso 1 1 calc R . . . .
C14 C 0.62036(15) -0.30409(9) 0.85542(8) 0.0226(3) Uani 1 1 d . . . . .
H14 H 0.5927 -0.3549 0.8085 0.027 Uiso 1 1 calc R . . . .
C12 C 0.65069(15) -0.24921(10) 1.00480(8) 0.0238(3) Uani 1 1 d . . . . .
H12 H 0.6434 -0.2626 1.0600 0.029 Uiso 1 1 calc R . . . .
C50 C 0.19634(16) 0.16284(10) 0.37293(9) 0.0273(3) Uani 1 1 d . . . . .
H50 H 0.1802 0.1165 0.3238 0.033 Uiso 1 1 calc R . . . .
C30 C 0.31885(14) 0.53150(9) 0.55977(8) 0.0214(3) Uani 1 1 d . . . . .
H30 H 0.3142 0.5127 0.4983 0.026 Uiso 1 1 calc R . . . .
C3 C 0.75173(14) 0.09872(9) 0.80560(8) 0.0212(3) Uani 1 1 d . . . . .
C19 C 0.93828(16) 0.24458(11) 0.90120(10) 0.0314(3) Uani 1 1 d . . . . .
H19 H 1.0189 0.2178 0.8880 0.038 Uiso 1 1 calc R . . . .
C22 C 0.70600(17) 0.32466(10) 0.94080(9) 0.0287(3) Uani 1 1 d . . . . .
H22 H 0.6260 0.3517 0.9544 0.034 Uiso 1 1 calc R . . . .
C17 C 0.46294(19) -0.48258(10) 0.87844(9) 0.0321(3) Uani 1 1 d . . . . .
H17A H 0.3868 -0.4523 0.8393 0.048 Uiso 1 1 calc GR . . . .
H17B H 0.4117 -0.5391 0.8974 0.048 Uiso 1 1 calc GR . . . .
H17C H 0.5328 -0.5036 0.8482 0.048 Uiso 1 1 calc GR . . . .
C48 C 0.10173(16) 0.27583(11) 0.45610(10) 0.0309(3) Uani 1 1 d . . . . .
H48 H 0.0206 0.3073 0.4624 0.037 Uiso 1 1 calc R . . . .
C21 C 0.85521(18) 0.37278(11) 0.97483(10) 0.0340(3) Uani 1 1 d . . . . .
H21 H 0.8776 0.4331 1.0110 0.041 Uiso 1 1 calc R . . . .
C29 C 1.27524(19) -0.16866(12) 0.89102(10) 0.0358(3) Uani 1 1 d . . . . .
H29A H 1.1863 -0.2207 0.8694 0.054 Uiso 1 1 calc GR . . . .
H29B H 1.2833 -0.1423 0.9502 0.054 Uiso 1 1 calc GR . . . .
H29C H 1.3674 -0.1949 0.8907 0.054 Uiso 1 1 calc GR . . . .
C49 C 0.07956(17) 0.20998(12) 0.38295(10) 0.0342(3) Uani 1 1 d . . . . .
H49 H -0.0162 0.1972 0.3396 0.041 Uiso 1 1 calc R . . . .
C20 C 0.97122(18) 0.33230(12) 0.95567(11) 0.0394(4) Uani 1 1 d . . . . .
H20 H 1.0738 0.3643 0.9797 0.047 Uiso 1 1 calc R . . . .
C46 C 0.2380(2) 0.98781(11) 0.54286(11) 0.0430(4) Uani 1 1 d . . . . .
H46A H 0.1393 0.9572 0.5025 0.065 Uiso 1 1 calc GR . . . .
H46B H 0.3164 0.9898 0.5130 0.065 Uiso 1 1 calc GR . . . .
H46C H 0.2326 1.0543 0.5644 0.065 Uiso 1 1 calc GR . . . .
C58 C 0.99186(19) 0.54484(14) 0.77351(13) 0.0475(4) Uani 1 1 d . . . . .
H58A H 1.0024 0.4827 0.7453 0.071 Uiso 1 1 calc GR . . . .
H58B H 0.9745 0.5353 0.8293 0.071 Uiso 1 1 calc GR . . . .
H58C H 1.0852 0.5922 0.7828 0.071 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
F25 C24 1.3477(16) . ?
F54 C53 1.3531(15) . ?
F55 C53 1.3474(16) . ?
F26 C24 1.3484(17) . ?
F56 C53 1.3472(15) . ?
F27 C24 1.3467(15) . ?
O16 C13 1.3733(16) . ?
O16 C17 1.4315(16) . ?
O28 C7 1.3721(15) . ?
O28 C29 1.4271(18) . ?
O45 C42 1.3699(16) . ?
O45 C46 1.4267(19) . ?
O57 C36 1.3727(17) . ?
O57 C58 1.401(2) . ?
C38 C33 1.3950(18) . ?
C38 C37 1.3874(18) . ?
C38 C30 1.5224(17) . ?
C4 C9 1.3869(18) . ?
C4 C5 1.4006(19) . ?
C4 C3 1.5315(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3959(17) . ?
C8 C7 1.3940(19) . ?
C9 C1 1.5179(17) . ?
C33 C32 1.5312(17) . ?
C33 C34 1.3907(18) . ?
C7 C6 1.4020(19) . ?
C40 H40 0.9500 . ?
C40 C39 1.4057(17) . ?
C40 C41 1.3819(19) . ?
C32 C47 1.5485(17) . ?
C32 C31 1.5549(17) . ?
C32 C53 1.5224(19) . ?
C39 C44 1.3887(18) . ?
C39 C30 1.5150(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3898(19) . ?
C36 C35 1.395(2) . ?
C36 C37 1.4046(19) . ?
C44 H44 0.9500 . ?
C44 C43 1.3979(19) . ?
C11 H11 0.9500 . ?
C11 C10 1.3982(18) . ?
C11 C12 1.3866(19) . ?
C18 C23 1.4011(18) . ?
C18 C3 1.5443(17) . ?
C18 C19 1.391(2) . ?
C51 H51 0.9500 . ?
C51 C52 1.3931(18) . ?
C51 C50 1.381(2) . ?
C47 C52 1.3920(18) . ?
C47 C48 1.3976(19) . ?
C13 C14 1.3942(18) . ?
C13 C12 1.3937(18) . ?
C1 H1 1.0000 . ?
C1 C2 1.5456(18) . ?
C1 C10 1.5118(18) . ?
C52 H52 0.9500 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C30 1.5483(19) . ?
C35 H35 0.9500 . ?
C35 C34 1.3956(19) . ?
C23 H23 0.9500 . ?
C23 C22 1.3910(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5567(18) . ?
C37 H37 0.9500 . ?
C10 C15 1.3950(18) . ?
C41 H41 0.9500 . ?
C41 C42 1.3970(19) . ?
C42 C43 1.3910(18) . ?
C24 C3 1.5253(18) . ?
C15 H15 0.9500 . ?
C15 C14 1.3898(19) . ?
C34 H34 0.9500 . ?
C6 H6 0.9500 . ?
C43 H43 0.9500 . ?
C14 H14 0.9500 . ?
C12 H12 0.9500 . ?
C50 H50 0.9500 . ?
C50 C49 1.387(2) . ?
C30 H30 1.0000 . ?
C19 H19 0.9500 . ?
C19 C20 1.396(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.387(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C48 H48 0.9500 . ?
C48 C49 1.392(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.383(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C49 H49 0.9500 . ?
C20 H20 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?

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
C13 O16 C17 116.62(10) . . ?
C7 O28 C29 117.34(11) . . ?
C42 O45 C46 117.21(11) . . ?
C36 O57 C58 118.04(13) . . ?
C33 C38 C30 110.70(11) . . ?
C37 C38 C33 121.22(12) . . ?
C37 C38 C30 128.08(12) . . ?
C9 C4 C5 119.87(12) . . ?
C9 C4 C3 110.02(11) . . ?
C5 C4 C3 130.11(12) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C7 C8 C9 117.98(12) . . ?
C4 C9 C8 121.80(12) . . ?
C4 C9 C1 110.95(11) . . ?
C8 C9 C1 127.24(12) . . ?
C38 C33 C32 110.14(11) . . ?
C34 C33 C38 119.95(12) . . ?
C34 C33 C32 129.88(12) . . ?
O28 C7 C8 123.97(12) . . ?
O28 C7 C6 115.20(12) . . ?
C8 C7 C6 120.82(12) . . ?
C39 C40 H40 119.3 . . ?
C41 C40 H40 119.3 . . ?
C41 C40 C39 121.41(12) . . ?
C33 C32 C47 112.42(10) . . ?
C33 C32 C31 100.74(10) . . ?
C47 C32 C31 112.40(10) . . ?
C53 C32 C33 111.56(10) . . ?
C53 C32 C47 108.90(10) . . ?
C53 C32 C31 110.67(10) . . ?
C40 C39 C30 120.58(11) . . ?
C44 C39 C40 117.57(12) . . ?
C44 C39 C30 121.84(11) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.11(12) . . ?
C6 C5 H5 120.4 . . ?
O57 C36 C35 124.34(12) . . ?
O57 C36 C37 115.00(12) . . ?
C35 C36 C37 120.66(12) . . ?
C39 C44 H44 119.1 . . ?
C39 C44 C43 121.83(12) . . ?
C43 C44 H44 119.1 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C12 C11 C10 121.23(12) . . ?
C23 C18 C3 120.66(12) . . ?
C19 C18 C23 118.09(12) . . ?
C19 C18 C3 121.25(12) . . ?
C52 C51 H51 119.8 . . ?
C50 C51 H51 119.8 . . ?
C50 C51 C52 120.49(12) . . ?
C52 C47 C32 120.94(11) . . ?
C52 C47 C48 118.09(12) . . ?
C48 C47 C32 120.97(11) . . ?
O16 C13 C14 123.78(11) . . ?
O16 C13 C12 116.40(11) . . ?
C12 C13 C14 119.82(12) . . ?
C9 C1 H1 108.2 . . ?
C9 C1 C2 101.49(10) . . ?
C2 C1 H1 108.2 . . ?
C10 C1 C9 115.61(10) . . ?
C10 C1 H1 108.2 . . ?
C10 C1 C2 114.75(10) . . ?
C51 C52 H52 119.5 . . ?
C47 C52 C51 120.94(12) . . ?
C47 C52 H52 119.5 . . ?
C32 C31 H31A 110.8 . . ?
C32 C31 H31B 110.8 . . ?
H31A C31 H31B 108.8 . . ?
C30 C31 C32 104.94(10) . . ?
C30 C31 H31A 110.8 . . ?
C30 C31 H31B 110.8 . . ?
F54 C53 C32 112.63(11) . . ?
F55 C53 F54 105.94(11) . . ?
F55 C53 C32 112.92(11) . . ?
F56 C53 F54 105.84(10) . . ?
F56 C53 F55 106.45(11) . . ?
F56 C53 C32 112.49(11) . . ?
C36 C35 H35 120.0 . . ?
C36 C35 C34 119.96(12) . . ?
C34 C35 H35 120.0 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.88(13) . . ?
C22 C23 H23 119.6 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.57(10) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C38 C37 C36 118.51(12) . . ?
C38 C37 H37 120.7 . . ?
C36 C37 H37 120.7 . . ?
C11 C10 C1 120.96(11) . . ?
C15 C10 C11 117.96(12) . . ?
C15 C10 C1 121.07(11) . . ?
C40 C41 H41 119.9 . . ?
C40 C41 C42 120.10(12) . . ?
C42 C41 H41 119.9 . . ?
O45 C42 C41 115.28(11) . . ?
O45 C42 C43 125.12(12) . . ?
C43 C42 C41 119.60(12) . . ?
F25 C24 F26 106.55(10) . . ?
F25 C24 C3 112.45(11) . . ?
F26 C24 C3 112.24(11) . . ?
F27 C24 F25 106.17(11) . . ?
F27 C24 F26 106.46(11) . . ?
F27 C24 C3 112.50(11) . . ?
C10 C15 H15 119.2 . . ?
C14 C15 C10 121.54(12) . . ?
C14 C15 H15 119.2 . . ?
C33 C34 C35 119.69(12) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.42(12) . . ?
C5 C6 H6 119.8 . . ?
C44 C43 H43 120.3 . . ?
C42 C43 C44 119.49(12) . . ?
C42 C43 H43 120.3 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.49(12) . . ?
C15 C14 H14 120.3 . . ?
C11 C12 C13 119.89(12) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C51 C50 H50 120.4 . . ?
C51 C50 C49 119.23(12) . . ?
C49 C50 H50 120.4 . . ?
C38 C30 C31 101.35(10) . . ?
C38 C30 H30 108.4 . . ?
C39 C30 C38 115.17(10) . . ?
C39 C30 C31 114.70(10) . . ?
C39 C30 H30 108.4 . . ?
C31 C30 H30 108.4 . . ?
C4 C3 C18 113.13(10) . . ?
C4 C3 C2 101.26(10) . . ?
C18 C3 C2 112.17(10) . . ?
C24 C3 C4 111.07(10) . . ?
C24 C3 C18 109.10(10) . . ?
C24 C3 C2 109.92(11) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.94(13) . . ?
C20 C19 H19 119.5 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.27(13) . . ?
C21 C22 H22 119.9 . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C47 C48 H48 119.6 . . ?
C49 C48 C47 120.79(13) . . ?
C49 C48 H48 119.6 . . ?
C22 C21 H21 120.3 . . ?
C20 C21 C22 119.50(13) . . ?
C20 C21 H21 120.3 . . ?
O28 C29 H29A 109.5 . . ?
O28 C29 H29B 109.5 . . ?
O28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C50 C49 C48 120.43(13) . . ?
C50 C49 H49 119.8 . . ?
C48 C49 H49 119.8 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.31(14) . . ?
C21 C20 H20 119.8 . . ?
O45 C46 H46A 109.5 . . ?
O45 C46 H46B 109.5 . . ?
O45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O57 C58 H58A 109.5 . . ?
O57 C58 H58B 109.5 . . ?
O57 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 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 1.188
_oxdiff_exptl_absorpt_empirical_full_min 0.774
####################################################################### 
# 
# 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_9926_emt074
_database_code_depnum_ccdc_archive 'CCDC 1875112'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 F4 O2'
_chemical_formula_sum            'C24 H20 F4 O2'
_chemical_formula_weight         416.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 F3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.76460(10)
_cell_length_b                   10.6788(2)
_cell_length_c                   20.8962(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.8210(10)
_cell_angle_gamma                90
_cell_volume                     1948.87(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7288
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      71.4460
_cell_measurement_theta_min      4.1210
_shelx_estimated_absorpt_T_max   0.843
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    0.979
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11506
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.277
_diffrn_reflns_theta_min         4.247
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00 -24.00   0.50    0.20    --  -41.22 -69.00-143.00  150
  2  ω    -32.00  -6.00   0.50    0.20    --  -41.22  69.00 -11.00   52
  3  ω     58.00 105.00   0.50    0.20    --   41.22  69.00 -11.00   94
  4  ω     20.00  55.00   0.50    0.20    --   41.22 -69.00-143.00   70
  5  ω     95.00 150.00   0.50    0.20    --  101.00  69.00 -11.00  110
  6  ω     69.00 120.00   0.50    0.20    --  101.00 -69.00-143.00  102
  7  ω    -49.00 -21.00   0.50    0.20    --  -41.22  21.00   0.00   56
  8  ω   -107.00 -33.00   0.50    0.20    --  -41.22 -32.00 120.00  148
  9  ω    -15.00  27.00   0.50    0.20    --  -41.22  21.00   0.00   84
 10  ω    -48.00  -9.00   0.50    0.20    --  -41.22  43.00-120.00   78
 11  ω    -25.00  24.00   0.50    0.20    --  -41.22  32.00 120.00   98
 12  ω     37.00 107.00   0.50    0.20    --   41.22  21.00 120.00  140
 13  ω     82.00 107.00   0.50    0.20    --   41.22  32.00 -30.00   50
 14  ω     24.00  53.00   0.50    0.20    --   41.22 -43.00 120.00   58
 15  ω    -19.00   9.00   0.50    0.20    --   41.22 -43.00 120.00   56
 16  ω    -16.00  58.00   0.50    0.20    --   41.22 -54.00-120.00  148
 17  ω     82.00 149.00   0.50    0.20    --  101.00  68.00 -60.00  134
 18  ω    109.00 152.00   0.50    0.20    --  101.00  93.00 -90.00   86
 19  ω     99.00 155.00   0.50    0.20    --  101.00  93.00 -60.00  112
 20  ω     44.00  97.00   0.50    0.20    --  101.00 -42.00 -90.00  106
 21  ω     40.00  98.00   0.50    0.20    --  101.00 -33.00 150.00  116
 22  ω     52.00 111.00   0.50    0.20    --  101.00 -50.00-180.00  118
 23  ω     90.00 155.00   0.50    0.20    --  101.00  50.00  30.00  130
 24  ω     56.00  82.00   0.50    0.20    --  101.00-133.00-180.00   52
 25  ω     89.00 117.00   0.50    0.20    --  101.00-133.00-180.00   56
 26  ω    113.00 147.00   0.50    0.20    --  101.00  17.00 -90.00   68
 27  ω     38.00 114.00   0.50    0.20    --  101.00 -42.00  30.00  152
 28  ω     97.00 125.00   0.50    0.20    --  101.00  33.00-180.00   56
 29  ω     49.00 109.00   0.50    0.20    --  101.00 -25.00-180.00  120
 30  ω     35.00 106.00   0.50    0.20    --  101.00 -17.00   0.00  142
 31  ω     94.00 119.00   0.50    0.20    --  101.00  69.00 -11.00   50
 32  ω    -51.00 -22.00   0.50    0.20    --  -41.22 -65.00  60.00   58
 33  ω    -92.00 -66.00   0.50    0.20    --  -41.22 -65.00  60.00   52
 34  ω    -90.00 -60.00   0.50    0.20    --  -41.22 -21.00 -90.00   60
 35  ω     80.00  86.50   0.50    0.20    --   41.22  65.00 150.00   13
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0482492000
_diffrn_orient_matrix_UB_12      0.0249149000
_diffrn_orient_matrix_UB_13      -0.0714562000
_diffrn_orient_matrix_UB_21      0.1000578000
_diffrn_orient_matrix_UB_22      -0.1104608000
_diffrn_orient_matrix_UB_23      -0.0188370000
_diffrn_orient_matrix_UB_31      -0.1371450000
_diffrn_orient_matrix_UB_32      -0.0893015000
_diffrn_orient_matrix_UB_33      0.0033741000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3377
_reflns_number_total             3803
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.55
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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         0.201
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.077
_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)+(0.0556P)²+0.3381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1010
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C14(H14), C25(H25), C6(H6), C21(H21), C15(H15), C5(H5),
 C24(H24), C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_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
F30 F 0.07557(9) 0.34809(7) 0.44379(4) 0.0303(2) Uani 1 1 d . . . . .
F27 F 0.29058(10) 0.50155(8) 0.74422(4) 0.0310(2) Uani 1 1 d . . . . .
F28 F 0.16600(9) 0.65604(8) 0.69906(4) 0.0334(2) Uani 1 1 d . . . . .
F29 F 0.38008(9) 0.68921(8) 0.75459(4) 0.0319(2) Uani 1 1 d . . . . .
O16 O 0.53539(11) 0.98850(8) 0.38040(4) 0.0246(2) Uani 1 1 d . . . . .
O18 O 0.25804(11) 1.07226(8) 0.36792(4) 0.0256(2) Uani 1 1 d . . . . .
C12 C 0.43611(14) 0.93188(11) 0.41840(6) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.29579(14) 0.51422(11) 0.60214(6) 0.0193(3) Uani 1 1 d . . . . .
C10 C 0.36545(14) 0.78252(11) 0.49804(6) 0.0200(3) Uani 1 1 d . . . . .
C11 C 0.47490(14) 0.83621(11) 0.46136(6) 0.0199(3) Uani 1 1 d . . . . .
H11 H 0.5774 0.8065 0.4660 0.024 Uiso 1 1 calc R . . . .
C9 C 0.31002(14) 0.56401(11) 0.54117(6) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.23663(15) 0.50856(12) 0.48685(6) 0.0212(3) Uani 1 1 d . . . . .
H8 H 0.2461 0.5414 0.4451 0.025 Uiso 1 1 calc R . . . .
C13 C 0.28458(15) 0.97689(11) 0.41088(6) 0.0207(3) Uani 1 1 d . . . . .
C20 C 0.54895(14) 0.53061(12) 0.67162(5) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.41154(14) 0.67919(11) 0.54521(6) 0.0201(3) Uani 1 1 d . . . . .
H1 H 0.5183 0.6526 0.5382 0.024 Uiso 1 1 calc R . . . .
C14 C 0.17592(15) 0.92359(12) 0.44693(6) 0.0225(3) Uani 1 1 d . . . . .
H14 H 0.0732 0.9527 0.4421 0.027 Uiso 1 1 calc R . . . .
C25 C 0.57713(15) 0.40446(12) 0.66038(6) 0.0225(3) Uani 1 1 d . . . . .
H25 H 0.4977 0.3537 0.6404 0.027 Uiso 1 1 calc R . . . .
C6 C 0.13125(15) 0.35294(12) 0.55569(6) 0.0241(3) Uani 1 1 d . . . . .
H6 H 0.0687 0.2812 0.5598 0.029 Uiso 1 1 calc R . . . .
C3 C 0.39218(14) 0.59052(11) 0.65238(6) 0.0197(3) Uani 1 1 d . . . . .
C7 C 0.14938(15) 0.40362(12) 0.49624(6) 0.0227(3) Uani 1 1 d . . . . .
C21 C 0.66763(15) 0.60237(13) 0.70156(6) 0.0250(3) Uani 1 1 d . . . . .
H21 H 0.6513 0.6887 0.7095 0.030 Uiso 1 1 calc R . . . .
C15 C 0.21663(15) 0.82710(12) 0.49043(6) 0.0223(3) Uani 1 1 d . . . . .
H15 H 0.1411 0.7917 0.5151 0.027 Uiso 1 1 calc R . . . .
C5 C 0.20644(14) 0.40889(12) 0.60978(6) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.1966 0.3753 0.6513 0.027 Uiso 1 1 calc R . . . .
C2 C 0.40697(15) 0.71659(12) 0.61647(6) 0.0218(3) Uani 1 1 d . . . . .
H2A H 0.3182 0.7715 0.6223 0.026 Uiso 1 1 calc R . . . .
H2B H 0.5020 0.7609 0.6323 0.026 Uiso 1 1 calc R . . . .
C17 C 0.69018(15) 0.94611(13) 0.38715(6) 0.0257(3) Uani 1 1 d . . . . .
H17A H 0.7526 0.9990 0.3613 0.039 Uiso 1 1 calc GR . . . .
H17B H 0.6948 0.8592 0.3724 0.039 Uiso 1 1 calc GR . . . .
H17C H 0.7296 0.9510 0.4324 0.039 Uiso 1 1 calc GR . . . .
C24 C 0.71960(16) 0.35152(13) 0.67789(6) 0.0262(3) Uani 1 1 d . . . . .
H24 H 0.7372 0.2656 0.6692 0.031 Uiso 1 1 calc R . . . .
C26 C 0.30724(15) 0.60947(13) 0.71205(6) 0.0243(3) Uani 1 1 d . . . . .
C23 C 0.83574(16) 0.42364(13) 0.70791(6) 0.0281(3) Uani 1 1 d . . . . .
H23 H 0.9328 0.3875 0.7202 0.034 Uiso 1 1 calc R . . . .
C22 C 0.80916(16) 0.54909(14) 0.71986(7) 0.0293(3) Uani 1 1 d . . . . .
H22 H 0.8882 0.5989 0.7407 0.035 Uiso 1 1 calc R . . . .
C19 C 0.10213(16) 1.10111(13) 0.34894(7) 0.0284(3) Uani 1 1 d . . . . .
H19A H 0.0973 1.1639 0.3146 0.043 Uiso 1 1 calc GR . . . .
H19B H 0.0531 1.1343 0.3858 0.043 Uiso 1 1 calc GR . . . .
H19C H 0.0488 1.0250 0.3333 0.043 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
F30 C7 1.3610(14) . ?
F27 C26 1.3483(15) . ?
F28 C26 1.3405(15) . ?
F29 C26 1.3517(15) . ?
O16 C12 1.3673(15) . ?
O16 C17 1.4260(15) . ?
O18 C13 1.3646(15) . ?
O18 C19 1.4242(16) . ?
C12 C11 1.3834(17) . ?
C12 C13 1.4087(18) . ?
C4 C9 1.3958(17) . ?
C4 C3 1.5266(17) . ?
C4 C5 1.3875(18) . ?
C10 C11 1.4000(17) . ?
C10 C1 1.5119(16) . ?
C10 C15 1.3851(18) . ?
C11 H11 0.9500 . ?
C9 C8 1.3892(17) . ?
C9 C1 1.5163(17) . ?
C8 H8 0.9500 . ?
C8 C7 1.3800(18) . ?
C13 C14 1.3852(18) . ?
C20 C25 1.3931(18) . ?
C20 C3 1.5382(17) . ?
C20 C21 1.3969(18) . ?
C1 H1 1.0000 . ?
C1 C2 1.5453(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.4003(17) . ?
C25 H25 0.9500 . ?
C25 C24 1.3914(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3764(18) . ?
C6 C5 1.3941(18) . ?
C3 C2 1.5521(17) . ?
C3 C26 1.5186(17) . ?
C21 H21 0.9500 . ?
C21 C22 1.3888(19) . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C24 H24 0.9500 . ?
C24 C23 1.384(2) . ?
C23 H23 0.9500 . ?
C23 C22 1.386(2) . ?
C22 H22 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C12 O16 C17 116.66(10) . . ?
C13 O18 C19 116.81(10) . . ?
O16 C12 C11 124.73(12) . . ?
O16 C12 C13 115.11(11) . . ?
C11 C12 C13 120.15(11) . . ?
C9 C4 C3 109.74(11) . . ?
C5 C4 C9 120.55(12) . . ?
C5 C4 C3 129.70(11) . . ?
C11 C10 C1 119.87(11) . . ?
C15 C10 C11 118.58(11) . . ?
C15 C10 C1 121.54(11) . . ?
C12 C11 C10 121.02(12) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C4 C9 C1 110.80(11) . . ?
C8 C9 C4 120.85(12) . . ?
C8 C9 C1 128.35(11) . . ?
C9 C8 H8 121.5 . . ?
C7 C8 C9 117.00(11) . . ?
C7 C8 H8 121.5 . . ?
O18 C13 C12 115.78(11) . . ?
O18 C13 C14 125.27(12) . . ?
C14 C13 C12 118.95(11) . . ?
C25 C20 C3 121.69(11) . . ?
C25 C20 C21 118.04(12) . . ?
C21 C20 C3 120.27(11) . . ?
C10 C1 C9 115.61(10) . . ?
C10 C1 H1 108.3 . . ?
C10 C1 C2 114.36(10) . . ?
C9 C1 H1 108.3 . . ?
C9 C1 C2 101.58(10) . . ?
C2 C1 H1 108.3 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.40(12) . . ?
C15 C14 H14 119.8 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.10(12) . . ?
C24 C25 H25 119.5 . . ?
C7 C6 H6 120.6 . . ?
C7 C6 C5 118.72(12) . . ?
C5 C6 H6 120.6 . . ?
C4 C3 C20 112.85(10) . . ?
C4 C3 C2 101.21(9) . . ?
C20 C3 C2 112.21(10) . . ?
C26 C3 C4 110.77(10) . . ?
C26 C3 C20 109.25(10) . . ?
C26 C3 C2 110.37(10) . . ?
F30 C7 C8 118.09(11) . . ?
F30 C7 C6 118.19(11) . . ?
C6 C7 C8 123.71(12) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.85(13) . . ?
C22 C21 H21 119.6 . . ?
C10 C15 C14 120.90(12) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C4 C5 C6 119.16(12) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C2 C3 104.57(10) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C25 C24 H24 119.9 . . ?
C23 C24 C25 120.18(13) . . ?
C23 C24 H24 119.9 . . ?
F27 C26 F29 106.00(10) . . ?
F27 C26 C3 112.12(10) . . ?
F28 C26 F27 106.34(10) . . ?
F28 C26 F29 106.05(10) . . ?
F28 C26 C3 113.03(10) . . ?
F29 C26 C3 112.76(11) . . ?
C24 C23 H23 120.3 . . ?
C24 C23 C22 119.41(13) . . ?
C22 C23 H23 120.3 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.41(13) . . ?
C23 C22 H22 119.8 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.713
####################################################################### 
# 
# 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_7072-9921_emt078
_database_code_depnum_ccdc_archive 'CCDC 1875106'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 F3'
_chemical_formula_sum            'C24 H21 F3'
_chemical_formula_weight         366.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'F3 C20'
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'
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                   9.7671(5)
_cell_length_b                   10.3099(4)
_cell_length_c                   19.8876(7)
_cell_angle_alpha                92.410(3)
_cell_angle_beta                 96.248(4)
_cell_angle_gamma                107.450(4)
_cell_volume                     1893.23(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6044
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3420
_cell_measurement_theta_min      3.0420
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.51
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24129
_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         27.499
_diffrn_reflns_theta_min         2.682
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  -57.0000  120.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega   54.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558 -133.0000   42.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega   48.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  178.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega   54.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558 -136.0000 -135.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega    5.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   57.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega   74.00  100.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  178.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   19.00   44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   57.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega  -49.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  -19.0000 -180.0000 106

#__ type_ start__ end____ width___ exp.time_
  9 omega   12.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   57.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
 10 omega   51.00   96.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558  178.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
 11 omega   -6.00   59.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       24.4558   77.0000   90.0000 65
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0762012000
_diffrn_orient_matrix_UB_12      -0.0262208000
_diffrn_orient_matrix_UB_13      -0.0083031000
_diffrn_orient_matrix_UB_21      0.0080706000
_diffrn_orient_matrix_UB_22      -0.0004461000
_diffrn_orient_matrix_UB_23      -0.0350169000
_diffrn_orient_matrix_UB_31      0.0043385000
_diffrn_orient_matrix_UB_32      -0.0674209000
_diffrn_orient_matrix_UB_33      0.0004198000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6685
_reflns_number_total             8686
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         8686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.028
_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)+(0.0469P)²+1.3111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1314
_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:
 C4(H4), C4B(H4B)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3B(H3BA,H3BB)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C15(H15), C6B(H6B), C14(H14), C20(H20), C19B(H19B),
 C8B(H8B), C17(H17), C22B(H22D), C21(H21), C12(H12), C9B(H9B), C6(H6), C9(H9),
 C18B(H18B), C18(H18), C21B(H21B), C8(H8), C14B(H14B), C16B(H16B), C12B(H12B),
 C15B(H15B), C13B(H13B)
2.d Idealised Me refined as rotating group:
 C23B(H23D,H23E,H23F), C24B(H24A,H24B,H24C), C23(H23A,H23B,H23C), C22(H22A,
 H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F2 F 0.53168(13) 0.54600(10) 0.22956(5) 0.0310(3) Uani 1 1 d . . . . .
F1 F 0.31682(13) 0.40596(12) 0.22591(6) 0.0377(3) Uani 1 1 d . . . . .
F1B F 0.12230(17) -0.41654(11) 0.41616(6) 0.0504(4) Uani 1 1 d . . . . .
F3B F -0.03216(15) -0.30768(12) 0.42511(6) 0.0462(3) Uani 1 1 d . . . . .
F2B F 0.17377(15) -0.23958(11) 0.48668(5) 0.0395(3) Uani 1 1 d . . . . .
F3 F 0.43536(14) 0.41020(12) 0.14060(6) 0.0403(3) Uani 1 1 d . . . . .
C10 C 0.53665(19) 0.33911(16) 0.31589(9) 0.0216(4) Uani 1 1 d . . . . .
C11 C 0.4200(2) 0.30448(18) 0.35372(10) 0.0283(4) Uani 1 1 d . . . . .
H11 H 0.3250 0.2627 0.3312 0.034 Uiso 1 1 calc R . . . .
C13 C 0.5785(2) 0.38974(18) 0.45730(10) 0.0289(4) Uani 1 1 d . . . . .
H13 H 0.5930 0.4059 0.5053 0.035 Uiso 1 1 calc R . . . .
C15 C 0.67368(19) 0.40132(16) 0.35057(9) 0.0219(4) Uani 1 1 d . . . . .
H15 H 0.7544 0.4277 0.3260 0.026 Uiso 1 1 calc R . . . .
C16 C 0.44287(18) -0.04775(16) 0.15871(9) 0.0197(3) Uani 1 1 d . . . . .
C6B C 0.03046(19) 0.07024(17) 0.29980(9) 0.0228(4) Uani 1 1 d . . . . .
H6B H 0.0007 0.0899 0.2553 0.027 Uiso 1 1 calc R . . . .
C14 C 0.6945(2) 0.42558(18) 0.42061(9) 0.0260(4) Uani 1 1 d . . . . .
H14 H 0.7894 0.4672 0.4435 0.031 Uiso 1 1 calc R . . . .
C20 C 0.3323(2) -0.29108(17) 0.13520(10) 0.0274(4) Uani 1 1 d . . . . .
H20 H 0.3033 -0.3792 0.1515 0.033 Uiso 1 1 calc R . . . .
C4 C 0.50919(19) 0.07584(16) 0.20865(9) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.5304 0.0442 0.2544 0.025 Uiso 1 1 calc R . . . .
C19B C -0.2613(2) -0.23474(18) 0.13854(10) 0.0291(4) Uani 1 1 d . . . . .
H19B H -0.3620 -0.2610 0.1422 0.035 Uiso 1 1 calc R . . . .
C8B C 0.0719(2) 0.12382(18) 0.42014(9) 0.0256(4) Uani 1 1 d . . . . .
H8B H 0.0694 0.1809 0.4585 0.031 Uiso 1 1 calc R . . . .
C1 C 0.4495(2) 0.41801(19) 0.20858(9) 0.0284(4) Uani 1 1 d . . . . .
C2 C 0.51236(19) 0.31168(17) 0.23826(9) 0.0228(4) Uani 1 1 d . . . . .
C17 C 0.41646(19) -0.03399(17) 0.08965(9) 0.0236(4) Uani 1 1 d . . . . .
H17 H 0.4454 0.0542 0.0733 0.028 Uiso 1 1 calc R . . . .
C22B C 0.0312(2) -0.1575(2) 0.12995(9) 0.0334(4) Uani 1 1 d . . . . .
H22D H 0.1319 -0.1304 0.1265 0.040 Uiso 1 1 calc R . . . .
C7B C 0.0252(2) 0.15403(18) 0.35586(9) 0.0253(4) Uani 1 1 d . . . . .
C19 C 0.3050(2) -0.27740(18) 0.06664(10) 0.0282(4) Uani 1 1 d . . . . .
C20B C -0.2147(2) -0.2218(2) 0.07471(10) 0.0356(5) Uani 1 1 d . . . . .
C17B C -0.01549(19) -0.17243(16) 0.19327(8) 0.0217(4) Uani 1 1 d . . . . .
C10B C 0.12445(19) -0.07093(16) 0.37352(9) 0.0216(4) Uani 1 1 d . . . . .
C7 C 0.8780(2) 0.25711(19) 0.15065(9) 0.0258(4) Uani 1 1 d . . . . .
C21 C 0.40135(19) -0.17853(17) 0.18069(9) 0.0226(4) Uani 1 1 d . . . . .
H21 H 0.4205 -0.1911 0.2274 0.027 Uiso 1 1 calc R . . . .
C5B C 0.07886(19) -0.04113(16) 0.30914(8) 0.0207(3) Uani 1 1 d . . . . .
C12 C 0.4411(2) 0.33010(19) 0.42337(10) 0.0313(4) Uani 1 1 d . . . . .
H12 H 0.3605 0.3065 0.4482 0.038 Uiso 1 1 calc R . . . .
C9B C 0.1220(2) 0.01252(18) 0.42990(9) 0.0259(4) Uani 1 1 d . . . . .
H9B H 0.1539 -0.0063 0.4742 0.031 Uiso 1 1 calc R . . . .
C3AA C 0.64855(19) 0.31028(17) 0.20742(8) 0.0219(4) Uani 1 1 d . . . . .
C1B C 0.1097(3) -0.29045(19) 0.42418(10) 0.0350(5) Uani 1 1 d . . . . .
C4B C 0.0942(2) -0.14370(16) 0.25591(8) 0.0224(4) Uani 1 1 d . . . . .
H4B H 0.1925 -0.1077 0.2414 0.027 Uiso 1 1 calc R . . . .
C23B C -0.0295(3) 0.2746(2) 0.34619(11) 0.0413(5) Uani 1 1 d . . . . .
H23D H 0.0433 0.3470 0.3276 0.062 Uiso 1 1 calc GR . . . .
H23E H -0.0481 0.3085 0.3900 0.062 Uiso 1 1 calc GR . . . .
H23F H -0.1194 0.2469 0.3146 0.062 Uiso 1 1 calc GR . . . .
C5 C 0.64580(19) 0.17682(17) 0.19110(8) 0.0210(3) Uani 1 1 d . . . . .
C6 C 0.75940(19) 0.15000(18) 0.16311(8) 0.0225(4) Uani 1 1 d . . . . .
H6 H 0.7564 0.0584 0.1524 0.027 Uiso 1 1 calc R . . . .
C11B C 0.3351(2) -0.17279(19) 0.37545(9) 0.0284(4) Uani 1 1 d . . . . .
C9 C 0.7656(2) 0.41824(18) 0.19474(9) 0.0259(4) Uani 1 1 d . . . . .
H9 H 0.7680 0.5097 0.2051 0.031 Uiso 1 1 calc R . . . .
C18B C -0.1632(2) -0.20986(17) 0.19659(9) 0.0254(4) Uani 1 1 d . . . . .
H18B H -0.1974 -0.2185 0.2396 0.030 Uiso 1 1 calc R . . . .
C2B C 0.1703(2) -0.20000(17) 0.36941(9) 0.0267(4) Uani 1 1 d . . . . .
C18 C 0.3487(2) -0.14648(19) 0.04415(9) 0.0268(4) Uani 1 1 d . . . . .
H18 H 0.3319 -0.1344 -0.0028 0.032 Uiso 1 1 calc R . . . .
C3 C 0.4094(2) 0.16619(17) 0.21436(10) 0.0263(4) Uani 1 1 d . . . . .
H3A H 0.3413 0.1326 0.2477 0.032 Uiso 1 1 calc R . . . .
H3B H 0.3530 0.1664 0.1699 0.032 Uiso 1 1 calc R . . . .
C21B C -0.0672(3) -0.1815(3) 0.07144(10) 0.0444(6) Uani 1 1 d . . . . .
H21B H -0.0327 -0.1701 0.0285 0.053 Uiso 1 1 calc R . . . .
C24B C -0.3221(3) -0.2512(3) 0.01173(13) 0.0621(8) Uani 1 1 d . . . . .
H24A H -0.3707 -0.3497 0.0043 0.093 Uiso 1 1 calc GR . . . .
H24B H -0.2718 -0.2193 -0.0273 0.093 Uiso 1 1 calc GR . . . .
H24C H -0.3941 -0.2039 0.0170 0.093 Uiso 1 1 calc GR . . . .
C3B C 0.0932(2) -0.26585(18) 0.29789(9) 0.0294(4) Uani 1 1 d . . . . .
H3BA H 0.1464 -0.3225 0.2778 0.035 Uiso 1 1 calc R . . . .
H3BB H -0.0071 -0.3234 0.3006 0.035 Uiso 1 1 calc R . . . .
C23 C 0.2290(3) -0.4001(2) 0.01784(13) 0.0473(6) Uani 1 1 d . . . . .
H23A H 0.2360 -0.4828 0.0386 0.071 Uiso 1 1 calc GR . . . .
H23B H 0.2746 -0.3915 -0.0239 0.071 Uiso 1 1 calc GR . . . .
H23C H 0.1269 -0.4057 0.0072 0.071 Uiso 1 1 calc GR . . . .
C22 C 1.0015(2) 0.2295(2) 0.11993(10) 0.0354(5) Uani 1 1 d . . . . .
H22A H 1.0845 0.2450 0.1551 0.053 Uiso 1 1 calc GR . . . .
H22B H 1.0287 0.2907 0.0839 0.053 Uiso 1 1 calc GR . . . .
H22C H 0.9718 0.1346 0.1008 0.053 Uiso 1 1 calc GR . . . .
C8 C 0.8790(2) 0.39073(19) 0.16670(9) 0.0291(4) Uani 1 1 d . . . . .
H8 H 0.9592 0.4645 0.1582 0.035 Uiso 1 1 calc R . . . .
C14B C 0.6368(3) -0.1241(3) 0.38548(11) 0.0473(6) Uani 1 1 d . . . . .
H14B H 0.7384 -0.1075 0.3887 0.057 Uiso 1 1 calc R . . . .
C16B C 0.4307(2) -0.0439(2) 0.39459(10) 0.0321(4) Uani 1 1 d . . . . .
H16B H 0.3938 0.0290 0.4049 0.038 Uiso 1 1 calc R . . . .
C12B C 0.3950(3) -0.2780(2) 0.36155(9) 0.0373(5) Uani 1 1 d . . . . .
H12B H 0.3327 -0.3676 0.3480 0.045 Uiso 1 1 calc R . . . .
C15B C 0.5801(3) -0.0190(2) 0.39905(11) 0.0423(5) Uani 1 1 d . . . . .
H15B H 0.6435 0.0707 0.4115 0.051 Uiso 1 1 calc R . . . .
C13B C 0.5435(3) -0.2523(3) 0.36737(10) 0.0455(6) Uani 1 1 d . . . . .
H13B H 0.5814 -0.3252 0.3586 0.055 Uiso 1 1 calc R . . . .


_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
F2 C1 1.344(2) . ?
F1 C1 1.348(2) . ?
F1B C1B 1.346(2) . ?
F3B C1B 1.346(3) . ?
F2B C1B 1.338(2) . ?
F3 C1 1.341(2) . ?
C10 C11 1.398(3) . ?
C10 C15 1.388(2) . ?
C10 C2 1.537(2) . ?
C11 C12 1.380(3) . ?
C13 C14 1.380(3) . ?
C13 C12 1.381(3) . ?
C15 C14 1.387(2) . ?
C16 C4 1.513(2) . ?
C16 C17 1.391(2) . ?
C16 C21 1.391(2) . ?
C6B C7B 1.396(2) . ?
C6B C5B 1.379(2) . ?
C20 C19 1.382(3) . ?
C20 C21 1.389(2) . ?
C4 C5 1.512(2) . ?
C4 C3 1.546(2) . ?
C19B C20B 1.393(3) . ?
C19B C18B 1.380(3) . ?
C8B C7B 1.389(3) . ?
C8B C9B 1.389(3) . ?
C1 C2 1.519(2) . ?
C2 C3AA 1.528(3) . ?
C2 C3 1.555(2) . ?
C17 C18 1.387(2) . ?
C22B C17B 1.384(3) . ?
C22B C21B 1.388(3) . ?
C7B C23B 1.504(3) . ?
C19 C18 1.397(3) . ?
C19 C23 1.507(3) . ?
C20B C21B 1.384(3) . ?
C20B C24B 1.501(3) . ?
C17B C4B 1.508(2) . ?
C17B C18B 1.387(3) . ?
C10B C5B 1.387(2) . ?
C10B C9B 1.391(2) . ?
C10B C2B 1.528(2) . ?
C7 C6 1.393(3) . ?
C7 C22 1.504(3) . ?
C7 C8 1.398(3) . ?
C5B C4B 1.515(2) . ?
C3AA C5 1.392(2) . ?
C3AA C9 1.390(3) . ?
C1B C2B 1.517(3) . ?
C4B C3B 1.538(2) . ?
C5 C6 1.387(2) . ?
C11B C2B 1.539(3) . ?
C11B C16B 1.385(3) . ?
C11B C12B 1.409(3) . ?
C9 C8 1.389(3) . ?
C2B C3B 1.559(2) . ?
C14B C15B 1.386(3) . ?
C14B C13B 1.369(4) . ?
C16B C15B 1.396(3) . ?
C12B C13B 1.385(3) . ?

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
C11 C10 C2 120.73(16) . . ?
C15 C10 C11 117.83(16) . . ?
C15 C10 C2 121.43(16) . . ?
C12 C11 C10 120.95(18) . . ?
C14 C13 C12 119.19(18) . . ?
C14 C15 C10 121.02(17) . . ?
C17 C16 C4 121.11(15) . . ?
C21 C16 C4 121.02(15) . . ?
C21 C16 C17 117.83(15) . . ?
C5B C6B C7B 119.85(16) . . ?
C13 C14 C15 120.46(18) . . ?
C19 C20 C21 121.33(16) . . ?
C16 C4 C3 112.96(14) . . ?
C5 C4 C16 115.60(14) . . ?
C5 C4 C3 101.94(13) . . ?
C18B C19B C20B 120.84(18) . . ?
C9B C8B C7B 121.81(16) . . ?
F2 C1 F1 106.21(14) . . ?
F2 C1 C2 112.46(15) . . ?
F1 C1 C2 112.39(16) . . ?
F3 C1 F2 106.33(15) . . ?
F3 C1 F1 106.22(15) . . ?
F3 C1 C2 112.72(15) . . ?
C10 C2 C3 112.64(15) . . ?
C1 C2 C10 107.92(14) . . ?
C1 C2 C3AA 111.18(15) . . ?
C1 C2 C3 109.90(15) . . ?
C3AA C2 C10 113.76(14) . . ?
C3AA C2 C3 101.37(13) . . ?
C18 C17 C16 121.29(16) . . ?
C17B C22B C21B 120.94(19) . . ?
C6B C7B C23B 120.20(17) . . ?
C8B C7B C6B 118.65(16) . . ?
C8B C7B C23B 121.15(16) . . ?
C20 C19 C18 118.02(16) . . ?
C20 C19 C23 120.87(18) . . ?
C18 C19 C23 121.11(19) . . ?
C19B C20B C24B 120.6(2) . . ?
C21B C20B C19B 117.99(18) . . ?
C21B C20B C24B 121.5(2) . . ?
C22B C17B C4B 119.63(17) . . ?
C22B C17B C18B 118.04(16) . . ?
C18B C17B C4B 122.30(16) . . ?
C5B C10B C9B 119.87(16) . . ?
C5B C10B C2B 110.30(14) . . ?
C9B C10B C2B 129.83(16) . . ?
C6 C7 C22 120.66(17) . . ?
C6 C7 C8 118.58(17) . . ?
C8 C7 C22 120.76(17) . . ?
C20 C21 C16 120.87(17) . . ?
C6B C5B C10B 121.09(15) . . ?
C6B C5B C4B 128.41(15) . . ?
C10B C5B C4B 110.48(14) . . ?
C11 C12 C13 120.53(18) . . ?
C8B C9B C10B 118.71(16) . . ?
C5 C3AA C2 110.40(15) . . ?
C9 C3AA C2 129.88(15) . . ?
C9 C3AA C5 119.72(17) . . ?
F1B C1B C2B 113.00(17) . . ?
F3B C1B F1B 106.03(16) . . ?
F3B C1B C2B 111.89(17) . . ?
F2B C1B F1B 106.55(16) . . ?
F2B C1B F3B 105.81(17) . . ?
F2B C1B C2B 113.01(16) . . ?
C17B C4B C5B 115.22(14) . . ?
C17B C4B C3B 116.13(14) . . ?
C5B C4B C3B 101.53(14) . . ?
C3AA C5 C4 111.06(15) . . ?
C6 C5 C4 128.13(15) . . ?
C6 C5 C3AA 120.80(16) . . ?
C5 C6 C7 120.12(16) . . ?
C16B C11B C2B 121.42(16) . . ?
C16B C11B C12B 117.2(2) . . ?
C12B C11B C2B 121.34(18) . . ?
C8 C9 C3AA 119.20(16) . . ?
C19B C18B C17B 121.20(17) . . ?
C10B C2B C11B 114.06(14) . . ?
C10B C2B C3B 100.97(14) . . ?
C1B C2B C10B 109.55(16) . . ?
C1B C2B C11B 109.38(16) . . ?
C1B C2B C3B 110.51(15) . . ?
C11B C2B C3B 112.12(15) . . ?
C17 C18 C19 120.65(17) . . ?
C4 C3 C2 105.45(14) . . ?
C20B C21B C22B 120.97(19) . . ?
C4B C3B C2B 104.40(13) . . ?
C9 C8 C7 121.57(17) . . ?
C13B C14B C15B 118.8(2) . . ?
C11B C16B C15B 121.34(19) . . ?
C13B C12B C11B 120.8(2) . . ?
C14B C15B C16B 120.5(2) . . ?
C14B C13B C12B 121.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_7072-10064_b38_ab_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1875108'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 F3 O2'
_chemical_formula_sum            'C24 H21 F3 O2'
_chemical_formula_weight         398.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 F3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.8501(9)
_cell_length_b                   10.1181(12)
_cell_length_c                   11.7209(10)
_cell_angle_alpha                98.214(9)
_cell_angle_beta                 105.322(9)
_cell_angle_gamma                103.258(9)
_cell_volume                     961.86(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1895
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.5790
_cell_measurement_theta_min      3.9410
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6591
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.973
_diffrn_reflns_theta_min         4.006
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -38.00   0.50    8.00    --  -41.22 -39.00 -84.00  128
  2  ω    -18.00  30.00   0.50    8.00    --   41.22 -39.00 -84.00   96
  3  ω     32.00  69.00   0.50    8.00    --   41.22  39.00  70.00   74
  4  ω     71.00 102.00   0.50    8.00    --   41.22  39.00  70.00   62
  5  ω     89.00 153.00   0.50   20.00    --  100.29  39.00  70.00  128
  6  ω     38.00 111.00   0.50   20.00    --  100.29 -39.00 -84.00  146
  7  ω    -96.00 -31.00   0.50    8.00    --  -41.22 138.00-150.00  130
  8  ω    -95.00 -24.00   0.50    8.00    --  -41.22 -54.00  90.00  142
  9  ω    -14.00  18.00   0.50    8.00    --  -41.22  32.00-150.00   64
 10  ω    -61.00  23.00   0.50    8.00    --  -41.22  65.00-120.00  168
 11  ω    -72.00 -43.00   0.50    8.00    --  -41.22 138.00  60.00   58
 12  ω    -45.00 -20.00   0.50    8.00    --  -41.22  32.00-150.00   50
 13  ω   -100.00 -62.00   0.50    8.00    --  -41.22 -32.00   0.00   76
 14  ω    -50.00   2.00   0.50    8.00    --  -41.22  39.00  70.00  104
 15  ω    -36.00 -11.00   0.50    8.00    --  -41.22 138.00  60.00   50
 16  ω    -29.00  11.00   0.50    8.00    --   41.22 -11.00 120.00   80
 17  ω     24.00  65.00   0.50    8.00    --   41.22 -11.00 120.00   82
 18  ω     32.00  78.00   0.50    8.00    --   41.22-138.00 150.00   92
 19  ω     34.00  94.00   0.50    8.00    --   41.22-138.00  60.00  120
 20  ω     -5.00  35.00   0.50    8.00    --   41.22 -65.00 -90.00   80
 21  ω     36.00  63.00   0.50    8.00    --   41.22  32.00-120.00   54
 22  ω     92.00 156.00   0.50   20.00    --  100.29  25.00  60.00  128
 23  ω     70.00 117.00   0.50   20.00    --  100.29-117.00-120.00   94
 24  ω     83.00 112.00   0.50   20.00    --  100.29 -42.00   0.00   58
 25  ω     92.00 129.00   0.50   20.00    --  100.29  25.00 120.00   74
 26  ω     57.00 108.00   0.50   20.00    --  100.29 -42.00 150.00  102
 27  ω    106.00 131.00   0.50   20.00    --  100.29-145.00 -60.00   50
 28  ω     81.00 108.00   0.50   20.00    --  100.29 -96.00 -60.00   54
 29  ω     83.00 110.00   0.50   20.00    --  100.29-117.00  60.00   54
 30  ω     91.00 147.00   0.50   20.00    --  100.29  17.00 -30.00  112
 31  ω     88.00 114.00   0.50   20.00    --  100.29  17.00-120.00   52
 32  ω     80.00 105.00   0.50   20.00    --  100.29  77.00   0.00   50
 33  ω     42.00 115.00   0.50   20.00    --  100.29 -77.00 -30.00  146
 34  ω     38.00  63.00   0.50   20.00    --  100.29-145.00 -60.00   50
 35  ω     85.00 111.00   0.50   20.00    --  100.29-117.00-180.00   52
 36  ω     58.00 109.00   0.50   20.00    --  100.29 -50.00-150.00  102
 37  ω     40.00 125.00   0.50   20.00    --  100.29 -77.00-150.00  170
 38  ω     35.00  86.00   0.50   20.00    --  100.29 -25.00-150.00  102
 39  ω    129.00 156.00   0.50   20.00    --  100.29  59.00 120.00   54
 40  ω     97.00 124.00   0.50   20.00    --  100.29  59.00 120.00   54
 41  ω     95.00 129.00   0.50   20.00    --  100.29-145.00  30.00   68
 42  ω     33.00 106.00   0.50   20.00    --  100.29 -96.00  90.00  146
 43  ω     56.00 116.00   0.50   20.00    --  100.29 -50.00 -30.00  120
 44  ω     37.00 111.00   0.50   20.00    --  100.29 -42.00  90.00  148
 45  ω     88.00 107.50   0.50   20.00    --  100.29  17.00  30.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0306810000
_diffrn_orient_matrix_UB_12      -0.1165001000
_diffrn_orient_matrix_UB_13      0.0695061000
_diffrn_orient_matrix_UB_21      -0.1701361000
_diffrn_orient_matrix_UB_22      0.0185648000
_diffrn_orient_matrix_UB_23      -0.0076616000
_diffrn_orient_matrix_UB_31      -0.0740979000
_diffrn_orient_matrix_UB_32      -0.1085496000
_diffrn_orient_matrix_UB_33      -0.1206656000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4435
_reflns_number_total             6591
_reflns_special_details          
;
 _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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         6591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0868
_refine_ls_restrained_S_all      1.028
_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)+(0.1785P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2319
_refine_ls_wR_factor_ref         0.2604
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.707(2)
 0.293(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C20(H20), C16(H16), C6(H6), C9(H9), C13(H13), C21(H21),
 C12(H12), C18(H18), C14(H14), C22(H22)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F3 F 0.2980(3) -0.0080(2) 0.7162(2) 0.0332(6) Uani 1 1 d . . . . .
F1 F 0.1193(3) 0.1060(2) 0.6868(2) 0.0352(6) Uani 1 1 d . . . . .
O1 O 0.1802(3) 0.6974(3) 0.5969(2) 0.0271(6) Uani 1 1 d . . . . .
F2 F 0.3254(3) 0.1735(2) 0.8493(2) 0.0345(6) Uani 1 1 d . . . . .
O2 O 0.2416(3) 0.6539(3) 0.8122(2) 0.0308(7) Uani 1 1 d . . . . .
C7 C 0.2255(4) 0.5783(4) 0.6090(4) 0.0241(8) Uani 1 1 d . . . . .
C3 C 0.3279(5) 0.1452(4) 0.5286(3) 0.0254(8) Uani 1 1 d . . . . .
H3A H 0.3998 0.0871 0.5142 0.030 Uiso 1 1 calc R . . . .
H3B H 0.2132 0.0869 0.4983 0.030 Uiso 1 1 calc R . . . .
C17 C 0.2702(5) 0.2337(4) 0.3309(3) 0.0261(8) Uani 1 1 d . . . . .
C24 C 0.2924(5) 0.6407(4) 0.9352(4) 0.0329(9) Uani 1 1 d . . . . .
H24A H 0.2230 0.5547 0.9443 0.049 Uiso 1 1 calc GR . . . .
H24B H 0.2829 0.7205 0.9882 0.049 Uiso 1 1 calc GR . . . .
H24C H 0.4062 0.6377 0.9577 0.049 Uiso 1 1 calc GR . . . .
C15 C 0.8312(5) 0.4086(4) 0.8125(4) 0.0294(9) Uani 1 1 d . . . . .
H15 H 0.8986 0.5018 0.8384 0.035 Uiso 1 1 calc R . . . .
C23 C 0.1446(5) 0.7274(4) 0.4785(4) 0.0284(9) Uani 1 1 d . . . . .
H23A H 0.0548 0.6513 0.4218 0.043 Uiso 1 1 calc GR . . . .
H23B H 0.2416 0.7371 0.4515 0.043 Uiso 1 1 calc GR . . . .
H23C H 0.1132 0.8143 0.4811 0.043 Uiso 1 1 calc GR . . . .
C10 C 0.3202(4) 0.3456(4) 0.6585(3) 0.0244(8) Uani 1 1 d . . . . .
C4 C 0.3512(5) 0.2704(4) 0.4671(3) 0.0263(8) Uani 1 1 d . . . . .
H4 H 0.4710 0.3094 0.4823 0.032 Uiso 1 1 calc R . . . .
C19 C 0.2988(6) 0.1811(4) 0.1313(4) 0.0355(10) Uani 1 1 d . . . . .
H19 H 0.3659 0.1700 0.0814 0.043 Uiso 1 1 calc R . . . .
C8 C 0.2575(4) 0.5547(4) 0.7280(3) 0.0240(8) Uani 1 1 d . . . . .
C20 C 0.1340(6) 0.1621(4) 0.0799(4) 0.0361(10) Uani 1 1 d . . . . .
H20 H 0.0870 0.1374 -0.0057 0.043 Uiso 1 1 calc R . . . .
C16 C 0.6629(5) 0.3823(4) 0.7647(3) 0.0265(8) Uani 1 1 d . . . . .
H16 H 0.6164 0.4579 0.7585 0.032 Uiso 1 1 calc R . . . .
C6 C 0.2474(5) 0.4893(4) 0.5177(4) 0.0264(8) Uani 1 1 d . . . . .
H6 H 0.2292 0.5072 0.4386 0.032 Uiso 1 1 calc R . . . .
C9 C 0.3030(5) 0.4365(4) 0.7522(4) 0.0252(8) Uani 1 1 d . . . . .
H9 H 0.3220 0.4180 0.8312 0.030 Uiso 1 1 calc R . . . .
C13 C 0.8016(5) 0.1637(4) 0.7847(4) 0.0299(9) Uani 1 1 d . . . . .
H13 H 0.8486 0.0887 0.7924 0.036 Uiso 1 1 calc R . . . .
C21 C 0.0372(6) 0.1789(5) 0.1526(4) 0.0379(10) Uani 1 1 d . . . . .
H21 H -0.0761 0.1662 0.1168 0.045 Uiso 1 1 calc R . . . .
C12 C 0.6347(5) 0.1369(4) 0.7357(4) 0.0264(8) Uani 1 1 d . . . . .
H12 H 0.5684 0.0434 0.7084 0.032 Uiso 1 1 calc R . . . .
C18 C 0.3657(5) 0.2166(4) 0.2562(4) 0.0302(9) Uani 1 1 d . . . . .
H18 H 0.4792 0.2294 0.2915 0.036 Uiso 1 1 calc R . . . .
C14 C 0.9011(5) 0.2998(4) 0.8227(4) 0.0304(9) Uani 1 1 d . . . . .
H14 H 1.0160 0.3181 0.8553 0.036 Uiso 1 1 calc R . . . .
C22 C 0.1040(5) 0.2140(4) 0.2775(4) 0.0318(9) Uani 1 1 d . . . . .
H22 H 0.0363 0.2248 0.3269 0.038 Uiso 1 1 calc R . . . .
C5 C 0.2967(5) 0.3727(4) 0.5437(3) 0.0250(8) Uani 1 1 d . . . . .
C11 C 0.5614(5) 0.2456(4) 0.7256(3) 0.0252(8) Uani 1 1 d . . . . .
C2 C 0.3760(5) 0.2141(4) 0.6653(3) 0.0242(8) Uani 1 1 d . . . . .
C1 C 0.2803(5) 0.1211(4) 0.7291(4) 0.0273(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 C1 1.344(4) . ?
F1 C1 1.343(4) . ?
O1 C7 1.369(4) . ?
O1 C23 1.432(5) . ?
F2 C1 1.349(5) . ?
O2 C24 1.428(5) . ?
O2 C8 1.363(4) . ?
C7 C8 1.415(5) . ?
C7 C6 1.381(5) . ?
C3 C4 1.545(5) . ?
C3 C2 1.555(5) . ?
C17 C4 1.518(5) . ?
C17 C18 1.387(6) . ?
C17 C22 1.392(6) . ?
C15 C16 1.392(6) . ?
C15 C14 1.385(5) . ?
C10 C9 1.393(5) . ?
C10 C5 1.384(5) . ?
C10 C2 1.526(5) . ?
C4 C5 1.517(5) . ?
C19 C20 1.379(6) . ?
C19 C18 1.385(6) . ?
C8 C9 1.389(5) . ?
C20 C21 1.378(7) . ?
C16 C11 1.401(6) . ?
C6 C5 1.394(5) . ?
C13 C12 1.382(5) . ?
C13 C14 1.390(6) . ?
C21 C22 1.384(6) . ?
C12 C11 1.402(5) . ?
C11 C2 1.542(5) . ?
C2 C1 1.527(5) . ?

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
C7 O1 C23 117.0(3) . . ?
C8 O2 C24 116.4(3) . . ?
O1 C7 C8 113.9(3) . . ?
O1 C7 C6 125.2(3) . . ?
C6 C7 C8 120.8(3) . . ?
C4 C3 C2 103.6(3) . . ?
C18 C17 C4 118.5(3) . . ?
C18 C17 C22 118.5(4) . . ?
C22 C17 C4 123.0(4) . . ?
C14 C15 C16 120.5(4) . . ?
C9 C10 C2 127.9(3) . . ?
C5 C10 C9 121.3(3) . . ?
C5 C10 C2 110.7(3) . . ?
C17 C4 C3 114.2(3) . . ?
C5 C4 C3 101.3(3) . . ?
C5 C4 C17 118.3(3) . . ?
C20 C19 C18 119.4(4) . . ?
O2 C8 C7 115.7(3) . . ?
O2 C8 C9 124.6(3) . . ?
C9 C8 C7 119.7(3) . . ?
C21 C20 C19 120.1(4) . . ?
C15 C16 C11 120.6(4) . . ?
C7 C6 C5 118.9(4) . . ?
C8 C9 C10 118.8(4) . . ?
C12 C13 C14 120.4(4) . . ?
C20 C21 C22 120.5(4) . . ?
C13 C12 C11 121.1(4) . . ?
C19 C18 C17 121.3(4) . . ?
C15 C14 C13 119.4(4) . . ?
C21 C22 C17 120.2(4) . . ?
C10 C5 C4 109.6(3) . . ?
C10 C5 C6 120.3(3) . . ?
C6 C5 C4 129.7(4) . . ?
C16 C11 C12 118.0(4) . . ?
C16 C11 C2 121.4(3) . . ?
C12 C11 C2 120.5(3) . . ?
C10 C2 C3 101.2(3) . . ?
C10 C2 C11 112.8(3) . . ?
C10 C2 C1 110.4(3) . . ?
C11 C2 C3 110.6(3) . . ?
C1 C2 C3 110.3(3) . . ?
C1 C2 C11 111.2(3) . . ?
F3 C1 F2 106.4(3) . . ?
F3 C1 C2 113.5(3) . . ?
F1 C1 F3 106.2(3) . . ?
F1 C1 F2 106.3(3) . . ?
F1 C1 C2 111.9(3) . . ?
F2 C1 C2 112.1(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 2.934
_oxdiff_exptl_absorpt_empirical_full_min 0.448
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.707(2) 6522 606 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.293(2) 6619 606 nmt 1.0037 0.0114 0.0056 -0.5109 -1.0022 0.0007 -0.7011
-0.0051 -1.0031

_twin_special_details            
;
Component 2 rotated by -179.9090° 
 around [0.92 -0.23 -0.32] (reciprocal) or [1.00 0.01 0.00] (direct)
;
####################################################################### 
# 
# 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_7072-9926_b-15a
_database_code_depnum_ccdc_archive 'CCDC 1875107'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F3 O'
_chemical_formula_sum            'C23 H19 F3 O'
_chemical_formula_weight         368.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C48 H40 F6 O1 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.9918(2)
_cell_length_b                   10.2089(2)
_cell_length_c                   10.5751(2)
_cell_angle_alpha                91.174(2)
_cell_angle_beta                 116.274(2)
_cell_angle_gamma                107.926(2)
_cell_volume                     904.65(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11409
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7490
_cell_measurement_theta_min      4.5710
_shelx_estimated_absorpt_T_max   0.834
_shelx_estimated_absorpt_T_min   0.704
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16434
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.964
_diffrn_reflns_theta_min         4.631
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00 -57.00   0.50    0.50    --  -41.49 127.00-173.00   52
  2  ω    -45.00  -8.00   0.50    0.50    --  -41.49 127.00-173.00   74
  3  ω    -93.00 -41.00   0.50    0.50    --  -41.49 143.00  -3.00  104
  4  ω     30.00  70.00   0.50    0.50    --   41.49-143.00 -58.00   80
  5  ω     46.00  91.00   0.50    0.50    --   41.49-127.00 110.00   90
  6  ω     70.00 103.00   0.50    1.50    --  101.00-127.00 110.00   66
  7  ω     83.00 116.00   0.50    1.50    --  101.00-143.00 -58.00   66
  8  ω    104.00 130.00   0.50    1.50    --  101.00 127.00-173.00   52
  9  ω    -35.00  24.00   0.50    0.50    --  -41.49  32.00   0.00  118
 10  ω    -67.00   1.00   0.50    0.50    --  -41.49  77.00   0.00  136
 11  ω    -51.00   2.00   0.50    0.50    --  -41.49  43.00  90.00  106
 12  ω    -92.00 -57.00   0.50    0.50    --  -41.49 -43.00   0.00   70
 13  ω     17.00  69.00   0.50    0.50    --   41.49 -89.00  90.00  104
 14  ω     34.00  93.00   0.50    0.50    --   41.49  32.00-180.00  118
 15  ω    -12.00  14.00   0.50    0.50    --   41.49 -43.00 150.00   52
 16  ω     74.00 103.00   0.50    0.50    --   41.49  43.00-120.00   58
 17  ω     40.00 105.00   0.50    0.50    --   41.49  32.00 -60.00  130
 18  ω     28.00  60.00   0.50    0.50    --   41.49  43.00-120.00   64
 19  ω     -8.00  45.00   0.50    0.50    --   41.49 -32.00 150.00  106
 20  ω    -14.00  12.00   0.50    0.50    --   41.49 -89.00  90.00   52
 21  ω     25.00  50.00   0.50    0.50    --   41.49 -43.00 150.00   50
 22  ω     76.00 101.00   0.50    0.50    --   41.49  32.00 150.00   50
 23  ω    -22.00  44.00   0.50    0.50    --   41.49 -32.00  30.00  132
 24  ω     93.00 134.00   0.50    1.50    --  101.00  33.00-120.00   82
 25  ω     82.00 155.00   0.50    1.50    --  101.00  68.00 120.00  146
 26  ω    116.00 157.00   0.50    1.50    --  101.00  93.00-120.00   82
 27  ω    101.00 153.00   0.50    1.50    --  101.00  33.00 -60.00  104
 28  ω     37.00 127.00   0.50    1.50    --  101.00 -87.00  90.00  180
 29  ω     82.00 107.00   0.50    1.50    --  101.00  93.00-120.00   50
 30  ω     94.00 157.00   0.50    1.50    --  101.00  77.00  90.00  126
 31  ω     38.00 125.00   0.50    1.50    --  101.00 -77.00 -60.00  174
 32  ω     40.00 112.00   0.50    1.50    --  101.00 -42.00  90.00  144
 33  ω     41.00 117.00   0.50    1.50    --  101.00 -50.00-180.00  152
 34  ω     53.00  78.00   0.50    1.50    --  101.00-111.00-120.00   50
 35  ω     93.00 119.00   0.50    1.50    --  101.00  33.00 120.00   52
 36  ω     64.00  89.00   0.50    1.50    --  101.00 -77.00 -90.00   50
 37  ω     92.00 152.00   0.50    1.50    --  101.00  25.00  60.00  120
 38  ω    103.00 129.00   0.50    1.50    --  101.00  59.00 -30.00   52
 39  ω    123.00 154.00   0.50    1.50    --  101.00  33.00-180.00   62
 40  ω     41.00 112.00   0.50    1.50    --  101.00 -42.00 -30.00  142
 41  ω     48.00 101.00   0.50    1.50    --  101.00 -42.00 -90.00  106
 42  ω     97.00 148.00   0.50    1.50    --  101.00  59.00-120.00  102
 43  ω     75.00 122.00   0.50    1.50    --  101.00-133.00  60.00   94
 44  ω     69.00 113.00   0.50    1.50    --  101.00-111.00 150.00   88
 45  ω     53.00 104.00   0.50    1.50    --  101.00-111.00 -60.00  102
 46  ω     95.00 124.00   0.50    1.50    --  101.00-133.00 -90.00   58
 47  ω     92.00 141.00   0.50    1.50    --  101.00  68.00-180.00   98
 48  ω     42.00 111.00   0.50    1.50    --  101.00 -59.00  90.00  138
 49  ω    100.00 156.00   0.50    1.50    --  101.00  59.00 150.00  112
 50  ω     86.00 111.00   0.50    1.50    --  101.00 143.00  -3.00   50
 51  ω     19.00  45.00   0.50    0.50    --   41.49  77.00-180.00   52
 52  ω    -42.00 -17.00   0.50    0.50    --    4.00 121.00  99.36   50
 53  ω    -27.00   4.00   0.50    0.50    --   16.00 116.00-105.70   62
 54  ω    -12.00  13.00   0.50    0.50    --   24.00 104.00  60.23   50
 55  ω    -40.00 -15.00   0.50    0.50    --   24.00 150.00-170.85   50
 56  ω     -3.00  22.00   0.50    0.50    --   28.00  95.00-120.68   50
 57  ω      3.00  28.00   0.50    0.50    --   32.00  89.00 -43.43   50
 58  ω      2.00  27.00   0.50    0.50    --   32.00  91.00 148.77   50
 59  ω      9.00  34.00   0.50    0.50    --   36.00  85.00 -94.02   50
 60  ω     10.00  35.00   0.50    0.50    --   36.00  82.00  32.15   50
 61  ω     15.00  40.00   0.50    0.50    --   40.00  79.00 -33.47   50
 62  ω     14.00  39.00   0.50    0.50    --   40.00  82.00  94.48   50
 63  ω     15.00  40.00   0.50    0.50    --   40.00  79.00-153.03   50
 64  ω     16.00  41.00   0.50    0.50    --   41.49  78.00 149.15   50
 65  ω     17.00  43.00   0.50    0.50    --   41.49  77.00 -90.00   52
 66  ω     18.00  43.00   0.50    0.50    --   44.00  82.00  -1.59   50
 67  ω     19.00  45.00   0.50    0.50    --   44.00  80.00  66.12   52
 68  ω     25.00  51.00   0.50    0.50    --   48.00  75.00 119.74   52
 69  ω     29.00  55.00   0.50    0.50    --   52.00  76.00  -7.14   52
 70  ω     28.00  54.00   0.50    0.50    --   52.00  75.00 -61.65   52
 71  ω     33.00  59.00   0.50    0.50    --   52.00  75.00  31.36   52
 72  ω     34.00  60.00   0.50    0.50    --   56.00  71.00-161.18   52
 73  ω     38.00  64.00   0.50    0.50    --   56.00  75.00 155.92   52
 74  ω     32.00  58.00   0.50    0.50    --   56.00  77.00 -58.68   52
 75  ω     40.00  65.00   0.50    0.50    --   60.00  65.00  82.66   50
 76  ω     41.00  67.00   0.50    0.50    --   60.00  65.00-106.54   52
 77  ω     35.00  66.00   0.50    0.50    --   60.00  77.00 135.39   62
 78  ω     71.00 113.00   0.50    0.50    --   60.00  65.00  82.66   84
 79  ω     42.00 102.00   0.50    0.50    --   64.00  73.00 -27.74  120
 80  ω     98.00 124.00   0.50    0.50    --   64.00  64.00 129.41   52
 81  ω     49.00  78.00   0.50    0.50    --   64.00  64.00 129.41   58
 82  ω     98.00 124.00   0.50    0.50    --   68.00  67.00  25.10   52
 83  ω     47.00  88.00   0.50    0.50    --   68.00  67.00  25.10   82
 84  ω     45.00  96.00   0.50    0.50    --   68.00  75.00 -43.07  102
 85  ω     43.00  79.00   0.50    0.50    --   68.00  77.00-150.16   72
 86  ω     54.00  79.00   0.50    1.50    --   76.00  70.00-108.05   50
 87  ω     53.00  97.00   0.50    1.50    --   76.00  73.00 172.06   88
 88  ω     53.00  79.00   0.50    1.50    --   76.00  72.00  88.99   52
 89  ω     60.00  86.00   0.50    1.50    --   76.00  53.00 173.82   52
 90  ω     93.00 134.00   0.50    1.50    --   84.00  73.00 -74.09   82
 91  ω     61.00  88.00   0.50    1.50    --   84.00  73.00 -74.09   54
 92  ω     64.00  90.00   0.50    1.50    --   88.00  76.00  87.95   52
 93  ω    123.00 149.00   0.50    1.50    --  101.00  77.00-150.00   52
 94  ω     76.00 102.00   0.50    1.50    --  101.00  77.00-150.00   52
 95  ω    120.00 156.00   0.50    1.50    --  101.00  77.00 -60.00   72
 96  ω     94.00 120.00   0.50    1.50    --  101.00  -8.00-180.00   52
 97  ω     76.00 116.00   0.50    1.50    --  101.00  77.00 -60.00   80
 98  ω     28.00  93.00   0.50    1.50    --  101.00  -8.00-180.00  130
 99  ω     73.00 109.00   0.50    1.50    --  101.00 -25.00 -30.00   72
100  ω     36.00  64.00   0.50    1.50    --  101.00 -25.00 -30.00   56
101  ω    117.00 153.00   0.50    1.50    --  101.00  77.00 -30.00   72
102  ω     76.00 103.00   0.50    1.50    --  101.00  77.00 -90.00   54
103  ω     77.00 103.00   0.50    1.50    --  101.00  77.00 -30.00   52
104  ω    122.00 148.00   0.50    1.50    --  101.00  77.00-180.00   52
105  ω    132.00 157.00   0.50    1.50    --  101.00  77.00   0.00   50
106  ω     76.00 117.00   0.50    1.50    --  101.00  77.00   0.00   82
107  ω     78.00 104.00   0.50    1.50    --  101.00  77.00-180.00   52
108  ω     76.00 129.00   0.50    1.50    --  101.00  77.00  60.00  106
109  ω     83.00 135.00   0.50    1.50    --  101.00  59.00-150.00  104
110  ω     76.00 101.00   0.50    1.50    --  101.00  77.00  90.00   50
111  ω     76.00 121.00   0.50    1.50    --  101.00  77.00  30.00   90
112  ω    132.00 157.00   0.50    1.50    --  101.00  77.00 120.00   50
113  ω     77.00 103.00   0.50    1.50    --  101.00 -33.00 120.00   52
114  ω     76.00 108.00   0.50    1.50    --  101.00  77.00 120.00   64
115  ω     41.00 105.00   0.50    1.50    --  101.00 -25.00-180.00  128
116  ω     77.00 103.00   0.50    1.50    --  101.00 -17.00  60.00   52
117  ω     76.00 102.00   0.50    1.50    --  101.00  77.00-120.00   52
118  ω     31.00  67.00   0.50    1.50    --  101.00 -17.00  60.00   72
119  ω    127.00 153.00   0.50    1.50    --  101.00  59.00   0.00   52
120  ω     85.00 111.00   0.50    1.50    --  101.00  59.00   0.00   52
121  ω     77.00 106.00   0.50    1.50    --  101.00  77.00 150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0332437000
_diffrn_orient_matrix_UB_12      -0.1370636000
_diffrn_orient_matrix_UB_13      0.0283627000
_diffrn_orient_matrix_UB_21      0.1715588000
_diffrn_orient_matrix_UB_22      0.0846473000
_diffrn_orient_matrix_UB_23      0.1160279000
_diffrn_orient_matrix_UB_31      -0.0569938000
_diffrn_orient_matrix_UB_32      -0.0090621000
_diffrn_orient_matrix_UB_33      0.1142319000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3338
_reflns_number_total             3535
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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         0.281
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.058
_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)+(0.0493P)²+0.2809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0897
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C17(H17), C19(H19), C20(H20), C11(H11), C18(H18), C14(H14),
 C21(H21), C8(H8), C13(H13), C12(H12), C15(H15)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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
F23 F 0.03776(7) 0.40356(7) 0.73481(7) 0.02467(16) Uani 1 1 d . . . . .
F24 F 0.10689(8) 0.22382(7) 0.73424(8) 0.02843(17) Uani 1 1 d . . . . .
F25 F 0.25213(8) 0.39661(8) 0.91340(7) 0.02740(17) Uani 1 1 d . . . . .
O26 O 0.67306(9) 0.16625(8) 0.66686(8) 0.02284(19) Uani 1 1 d . . . . .
C9 C 0.37336(12) 0.35323(11) 0.70179(11) 0.0168(2) Uani 1 1 d . . . . .
C16 C 0.14793(12) 0.30491(11) 0.30739(11) 0.0167(2) Uani 1 1 d . . . . .
C6 C 0.56992(12) 0.22767(11) 0.66949(12) 0.0185(2) Uani 1 1 d . . . . .
C4 C 0.36581(12) 0.32794(10) 0.56882(11) 0.0164(2) Uani 1 1 d . . . . .
C5 C 0.46261(12) 0.26433(11) 0.54981(11) 0.0177(2) Uani 1 1 d . . . . .
H5 H 0.4558 0.2465 0.4582 0.021 Uiso 1 1 calc R . . . .
C7 C 0.57824(12) 0.25367(11) 0.80430(11) 0.0193(2) Uani 1 1 d . . . . .
H7 H 0.6517 0.2282 0.8847 0.023 Uiso 1 1 calc R . . . .
C3 C 0.25190(12) 0.38835(11) 0.45900(11) 0.0166(2) Uani 1 1 d . . . . .
H3 H 0.3157 0.4835 0.4545 0.020 Uiso 1 1 calc R . . . .
C1 C 0.26329(12) 0.43166(11) 0.69524(11) 0.0170(2) Uani 1 1 d . . . . .
C17 C 0.07304(13) 0.15946(11) 0.28167(12) 0.0198(2) Uani 1 1 d . . . . .
H17 H 0.0927 0.1110 0.3600 0.024 Uiso 1 1 calc R . . . .
C10 C 0.35388(12) 0.58962(11) 0.75693(11) 0.0168(2) Uani 1 1 d . . . . .
C22 C 0.16615(13) 0.36477(12) 0.76990(12) 0.0205(2) Uani 1 1 d . . . . .
C19 C -0.06038(13) 0.15543(12) 0.02665(12) 0.0220(2) Uani 1 1 d . . . . .
H19 H -0.1310 0.1048 -0.0685 0.026 Uiso 1 1 calc R . . . .
C20 C 0.01304(13) 0.29971(12) 0.05095(12) 0.0214(2) Uani 1 1 d . . . . .
H20 H -0.0077 0.3479 -0.0276 0.026 Uiso 1 1 calc R . . . .
C2 C 0.15141(12) 0.40623(11) 0.53054(11) 0.0180(2) Uani 1 1 d . . . . .
H2A H 0.0558 0.3209 0.5006 0.022 Uiso 1 1 calc R . . . .
H2B H 0.1166 0.4870 0.5038 0.022 Uiso 1 1 calc R . . . .
C11 C 0.27598(13) 0.67821(12) 0.77059(12) 0.0205(2) Uani 1 1 d . . . . .
H11 H 0.1660 0.6399 0.7450 0.025 Uiso 1 1 calc R . . . .
C18 C -0.03021(13) 0.08504(12) 0.14203(12) 0.0223(2) Uani 1 1 d . . . . .
H18 H -0.0800 -0.0138 0.1256 0.027 Uiso 1 1 calc R . . . .
C14 C 0.59719(13) 0.79305(12) 0.84435(12) 0.0220(2) Uani 1 1 d . . . . .
H14 H 0.7069 0.8320 0.8689 0.026 Uiso 1 1 calc R . . . .
C21 C 0.11734(12) 0.37408(11) 0.19059(12) 0.0187(2) Uani 1 1 d . . . . .
H21 H 0.1680 0.4727 0.2064 0.022 Uiso 1 1 calc R . . . .
C8 C 0.48068(13) 0.31593(11) 0.82133(11) 0.0187(2) Uani 1 1 d . . . . .
H8 H 0.4864 0.3331 0.9126 0.022 Uiso 1 1 calc R . . . .
C13 C 0.51916(14) 0.87914(12) 0.85852(12) 0.0243(2) Uani 1 1 d . . . . .
H13 H 0.5752 0.9768 0.8935 0.029 Uiso 1 1 calc R . . . .
C12 C 0.35796(14) 0.82127(12) 0.82106(12) 0.0239(2) Uani 1 1 d . . . . .
H12 H 0.3038 0.8798 0.8300 0.029 Uiso 1 1 calc R . . . .
C15 C 0.51514(13) 0.64947(11) 0.79416(11) 0.0188(2) Uani 1 1 d . . . . .
H15 H 0.5699 0.5915 0.7852 0.023 Uiso 1 1 calc R . . . .
C27 C 0.68101(14) 0.15092(13) 0.53565(13) 0.0247(2) Uani 1 1 d . . . . .
H27A H 0.5771 0.0890 0.4596 0.037 Uiso 1 1 calc GR . . . .
H27B H 0.7623 0.1104 0.5488 0.037 Uiso 1 1 calc GR . . . .
H27C H 0.7090 0.2429 0.5088 0.037 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
F23 C22 1.3555(12) . ?
F24 C22 1.3487(13) . ?
F25 C22 1.3417(13) . ?
O26 C6 1.3706(13) . ?
O26 C27 1.4326(14) . ?
C9 C4 1.3888(15) . ?
C9 C1 1.5272(14) . ?
C9 C8 1.4014(14) . ?
C16 C3 1.5166(14) . ?
C16 C17 1.3993(15) . ?
C16 C21 1.3972(15) . ?
C6 C5 1.3987(15) . ?
C6 C7 1.4056(16) . ?
C4 C5 1.3969(15) . ?
C4 C3 1.5218(14) . ?
C5 H5 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.3852(15) . ?
C3 H3 1.0000 . ?
C3 C2 1.5471(15) . ?
C1 C10 1.5431(14) . ?
C1 C22 1.5246(15) . ?
C1 C2 1.5588(14) . ?
C17 H17 0.9500 . ?
C17 C18 1.3946(15) . ?
C10 C11 1.4043(15) . ?
C10 C15 1.3953(15) . ?
C19 H19 0.9500 . ?
C19 C20 1.3879(17) . ?
C19 C18 1.3927(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.3956(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C12 1.3905(16) . ?
C18 H18 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.3866(16) . ?
C14 C15 1.3948(15) . ?
C21 H21 0.9500 . ?
C8 H8 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.3928(17) . ?
C12 H12 0.9500 . ?
C15 H15 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C6 O26 C27 117.27(8) . . ?
C4 C9 C1 110.98(9) . . ?
C4 C9 C8 120.18(10) . . ?
C8 C9 C1 128.69(10) . . ?
C17 C16 C3 121.15(9) . . ?
C21 C16 C3 119.97(9) . . ?
C21 C16 C17 118.76(10) . . ?
O26 C6 C5 124.36(10) . . ?
O26 C6 C7 115.17(9) . . ?
C5 C6 C7 120.47(10) . . ?
C9 C4 C5 121.54(9) . . ?
C9 C4 C3 110.73(9) . . ?
C5 C4 C3 127.56(9) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 C6 118.10(10) . . ?
C4 C5 H5 121.0 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.79(10) . . ?
C8 C7 H7 119.6 . . ?
C16 C3 C4 117.79(9) . . ?
C16 C3 H3 108.2 . . ?
C16 C3 C2 111.92(8) . . ?
C4 C3 H3 108.2 . . ?
C4 C3 C2 102.03(8) . . ?
C2 C3 H3 108.2 . . ?
C9 C1 C10 112.73(8) . . ?
C9 C1 C2 101.53(8) . . ?
C10 C1 C2 110.89(8) . . ?
C22 C1 C9 110.49(9) . . ?
C22 C1 C10 111.07(9) . . ?
C22 C1 C2 109.75(8) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.58(10) . . ?
C18 C17 H17 119.7 . . ?
C11 C10 C1 121.51(9) . . ?
C15 C10 C1 120.30(9) . . ?
C15 C10 C11 118.11(10) . . ?
F23 C22 C1 113.00(9) . . ?
F24 C22 F23 105.40(8) . . ?
F24 C22 C1 111.94(9) . . ?
F25 C22 F23 106.61(9) . . ?
F25 C22 F24 106.72(9) . . ?
F25 C22 C1 112.65(9) . . ?
C20 C19 H19 120.1 . . ?
C20 C19 C18 119.84(10) . . ?
C18 C19 H19 120.1 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.12(10) . . ?
C21 C20 H20 119.9 . . ?
C3 C2 C1 105.62(8) . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.79(10) . . ?
C12 C11 H11 119.6 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.07(10) . . ?
C19 C18 H18 120.0 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.22(10) . . ?
C15 C14 H14 119.9 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.65(10) . . ?
C20 C21 H21 119.7 . . ?
C9 C8 H8 120.5 . . ?
C7 C8 C9 118.92(10) . . ?
C7 C8 H8 120.5 . . ?
C14 C13 H13 120.3 . . ?
C14 C13 C12 119.47(10) . . ?
C12 C13 H13 120.3 . . ?
C11 C12 C13 120.34(10) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.07(10) . . ?
C14 C15 H15 119.5 . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.770
####################################################################### 
# 
# 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_7072-9926_b-9a
_database_code_depnum_ccdc_archive 'CCDC 1875110'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 F3'
_chemical_formula_sum            'C24 H21 F3'
_chemical_formula_weight         366.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.9463(3)
_cell_length_b                   10.2875(3)
_cell_length_c                   11.0964(3)
_cell_angle_alpha                70.184(2)
_cell_angle_beta                 86.437(2)
_cell_angle_gamma                76.947(2)
_cell_volume                     935.84(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8382
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.3960
_cell_measurement_theta_min      4.1860
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.777
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17525
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.028
_diffrn_reflns_theta_min         4.236
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  28.00   0.50    0.23    --   41.22 -99.00-107.00   90
  2  ω     36.00  69.00   0.50    0.23    --   41.22 -99.00-107.00   66
  3  ω     75.00 109.00   0.50    0.93    --  101.00 -99.00-107.00   68
  4  ω    110.00 153.00   0.50    0.93    --  101.00  99.00  -1.00   86
  5  ω    -22.00  13.00   0.50    0.23    --  -41.22  77.00 -30.00   70
  6  ω   -108.00 -36.00   0.50    0.23    --  -41.22 -21.00 -90.00  144
  7  ω     -8.00  18.00   0.50    0.23    --  -41.22  99.00  -1.00   52
  8  ω    -69.00 -26.00   0.50    0.23    --  -41.22 -11.00-180.00   86
  9  ω    -40.00 -14.00   0.50    0.23    --  -41.22  21.00-120.00   52
 10  ω    -88.00 -62.00   0.50    0.23    --  -41.22 138.00  90.00   52
 11  ω    -64.00 -18.00   0.50    0.23    --  -41.22 138.00   0.00   92
 12  ω    -91.00 -66.00   0.50    0.23    --  -41.22 138.00   0.00   50
 13  ω    -53.00 -20.00   0.50    0.23    --  -41.22 138.00  90.00   66
 14  ω    -46.00 -19.00   0.50    0.23    --  -41.22  65.00-120.00   54
 15  ω     -7.00  28.00   0.50    0.23    --  -41.22  21.00-120.00   70
 16  ω   -115.00 -73.00   0.50    0.23    --  -41.22 -11.00-180.00   84
 17  ω    -61.00 -36.00   0.50    0.23    --  -41.22  77.00 -30.00   50
 18  ω    -16.00  14.00   0.50    0.23    --   41.22 -77.00  60.00   60
 19  ω    -19.00  11.00   0.50    0.23    --   41.22 -65.00 120.00   60
 20  ω     42.00  67.00   0.50    0.23    --   41.22 -77.00  60.00   50
 21  ω    -13.00  55.00   0.50    0.23    --   41.22 -54.00 -60.00  136
 22  ω     74.00 100.00   0.50    0.23    --   41.22  65.00 -90.00   52
 23  ω     25.00  65.00   0.50    0.23    --   41.22  65.00 -90.00   80
 24  ω     16.00  48.00   0.50    0.23    --   41.22 -65.00 120.00   64
 25  ω     53.00 121.00   0.50    0.93    --  101.00 -77.00 -90.00  136
 26  ω     92.00 156.00   0.50    0.93    --  101.00  42.00-150.00  128
 27  ω     38.00  66.00   0.50    0.93    --  101.00 -59.00 150.00   56
 28  ω     86.00 156.00   0.50    0.93    --  101.00  50.00  60.00  140
 29  ω     89.00 126.00   0.50    0.93    --  101.00 -87.00 -60.00   74
 30  ω     47.00 124.00   0.50    0.93    --  101.00-133.00  90.00  154
 31  ω     83.00 125.00   0.50    0.93    --  101.00 111.00 -30.00   84
 32  ω    132.00 157.00   0.50    0.93    --  101.00 111.00 -30.00   50
 33  ω     58.00  84.00   0.50    0.93    --  101.00-133.00 150.00   52
 34  ω     76.00 110.00   0.50    0.93    --  101.00 -25.00 -90.00   68
 35  ω     61.00 116.00   0.50    0.93    --  101.00 -59.00  30.00  110
 36  ω     50.00 118.00   0.50    0.93    --  101.00 -59.00 -90.00  136
 37  ω     37.00 127.00   0.50    0.93    --  101.00 -87.00  60.00  180
 38  ω     81.00 110.00   0.50    0.93    --  101.00 -33.00-120.00   58
 39  ω     41.00  67.00   0.50    0.93    --  101.00 -33.00-120.00   52
 40  ω     95.00 147.00   0.50    0.93    --  101.00 111.00-120.00  104
 41  ω    112.00 145.00   0.50    0.93    --  101.00  68.00 150.00   66
 42  ω    106.00 151.00   0.50    0.93    --  101.00 111.00-150.00   90
 43  ω     75.00 113.00   0.50    0.93    --  101.00-111.00 150.00   76
 44  ω     94.00 130.00   0.50    0.93    --  101.00 -93.00-180.00   72
 45  ω    132.00 157.00   0.50    0.93    --  101.00  59.00-120.00   50
 46  ω    101.00 127.00   0.50    0.93    --  101.00  59.00-120.00   52
 47  ω     63.00  88.00   0.50    0.93    --  101.00 -93.00-180.00   50
 48  ω     81.00 106.00   0.50    0.93    --  101.00  68.00 150.00   50
 49  ω     92.00 156.00   0.50    0.93    --  101.00  93.00  30.00  128
 50  ω     34.00  69.00   0.50    0.93    --  101.00 -25.00 -90.00   70
 51  ω     97.00 149.00   0.50    0.93    --  101.00  68.00 120.00  104
 52  ω     45.00 115.00   0.50    0.93    --  101.00-111.00-120.00  140
 53  ω     34.00  59.00   0.50    0.93    --  101.00 -93.00-180.00   50
 54  ω     91.00 116.00   0.50    0.93    --  101.00-133.00 150.00   50
 55  ω     82.00 120.00   0.50    0.93    --  101.00 -59.00 150.00   76
 56  ω     95.00 121.00   0.50    0.93    --  101.00  42.00-180.00   52
 57  ω    100.00 125.00   0.50    0.93    --  101.00  42.00 -30.00   50
 58  ω     78.00 153.00   0.50    0.93    --  101.00  77.00 -90.00  150
 59  ω    107.00 133.00   0.50    0.93    --  101.00  99.00  -1.00   52
 60  ω    -35.00   0.00   0.50    0.23    --    4.00 109.00-136.05   70
 61  ω    -17.00   9.00   0.50    0.23    --   20.00 106.00 -13.24   52
 62  ω    -43.00 -18.00   0.50    0.23    --   24.00 153.00  58.15   50
 63  ω     -2.00  23.00   0.50    0.23    --   28.00  92.00-110.77   50
 64  ω      3.00  28.00   0.50    0.23    --   32.00  89.00   7.52   50
 65  ω      3.00  28.00   0.50    0.23    --   32.00  90.00 -49.88   50
 66  ω      9.00  34.00   0.50    0.23    --   36.00  84.00-179.91   50
 67  ω     15.00  40.00   0.50    0.23    --   40.00  80.00 -13.19   50
 68  ω     15.00  40.00   0.50    0.23    --   40.00  81.00 -76.75   50
 69  ω     19.00  44.00   0.50    0.23    --   44.00  81.00-159.25   50
 70  ω     19.00  44.00   0.50    0.23    --   44.00  79.00 -41.99   50
 71  ω     18.00  43.00   0.50    0.23    --   44.00  82.00 127.84   50
 72  ω     19.00  44.00   0.50    0.23    --   44.00  80.00 160.01   50
 73  ω     19.00  44.00   0.50    0.23    --   44.00  79.00 108.72   50
 74  ω     18.00  43.00   0.50    0.23    --   44.00  82.00  68.70   50
 75  ω     19.00  44.00   0.50    0.23    --   44.00  79.00  32.25   50
 76  ω     23.00  49.00   0.50    0.23    --   48.00  76.00 -99.05   52
 77  ω     35.00  61.00   0.50    0.23    --   52.00  64.00 -81.33   52
 78  ω     27.00  54.00   0.50    0.23    --   52.00  77.00 158.71   54
 79  ω     29.00  55.00   0.50    0.23    --   52.00  73.00  15.97   52
 80  ω     75.00 101.00   0.50    0.23    --   52.00  77.00 158.71   52
 81  ω     57.00  84.00   0.50    0.23    --   52.00  73.00  15.97   54
 82  ω     37.00  63.00   0.50    0.23    --   52.00  72.00 118.44   52
 83  ω     27.00  53.00   0.50    0.23    --   52.00  76.00 -18.11   52
 84  ω     29.00  55.00   0.50    0.23    --   52.00  76.00-152.86   52
 85  ω     31.00  61.00   0.50    0.23    --   56.00  76.00  65.51   60
 86  ω     46.00  86.00   0.50    0.23    --   60.00  62.00 161.37   80
 87  ω     39.00  69.00   0.50    0.23    --   64.00  77.00-145.35   60
 88  ω     42.00  68.00   0.50    0.23    --   64.00  74.00 -66.43   52
 89  ω     40.00  92.00   0.50    0.23    --   64.00  76.00  27.22  104
 90  ω     47.00  73.00   0.50    0.23    --   64.00  58.00 150.53   52
 91  ω     52.00  99.00   0.50    0.23    --   68.00  66.00 111.94   94
 92  ω     50.00  83.00   0.50    0.23    --   68.00  62.00 102.39   66
 93  ω     50.00  75.00   0.50    0.93    --   72.00  70.00-119.56   50
 94  ω     53.00 112.00   0.50    0.93    --   76.00  74.00 -15.64  118
 95  ω     59.00  86.00   0.50    0.93    --   76.00  61.00 -30.36   54
 96  ω    105.00 138.00   0.50    0.93    --   76.00  77.00  51.52   66
 97  ω     52.00 101.00   0.50    0.93    --   76.00  77.00  51.52   98
 98  ω     57.00  83.00   0.50    0.93    --   80.00  73.00 -67.68   52
 99  ω     64.00 115.00   0.50    0.93    --   84.00  67.00-104.32  102
100  ω     70.00  96.00   0.50    0.93    --   88.00  62.00 -89.70   52
101  ω     73.00  99.00   0.50    0.93    --   96.00  73.00 -68.93   52
102  ω    109.00 157.00   0.50    0.93    --  101.00 111.00 -90.00   96
103  ω     84.00 119.00   0.50    0.93    --  101.00  59.00  30.00   70
104  ω     83.00 136.00   0.50    0.93    --  101.00  59.00-180.00  106
105  ω    122.00 148.00   0.50    0.93    --  101.00  68.00   0.00   52
106  ω     72.00  98.00   0.50    0.93    --  101.00 -33.00  30.00   52
107  ω     36.00  62.00   0.50    0.93    --  101.00 -33.00  30.00   52
108  ω     81.00 110.00   0.50    0.93    --  101.00  68.00   0.00   58
109  ω     76.00 102.00   0.50    0.93    --  101.00  77.00 120.00   52
110  ω     78.00 105.00   0.50    0.93    --  101.00  77.00   0.00   54
111  ω     76.00 140.00   0.50    0.93    --  101.00  77.00 -30.00  128
112  ω     66.00 110.00   0.50    0.93    --  101.00 -33.00 -60.00   88
113  ω     77.00 123.00   0.50    0.93    --  101.00  77.00  84.38   92
114  ω    115.00 141.00   0.50    0.93    --  101.00  77.00 150.00   52
115  ω     77.00 102.00   0.50    0.93    --  101.00  77.00 150.00   50
116  ω    132.00 157.00   0.50    0.93    --  101.00  77.00  60.00   50
117  ω     78.00 103.00   0.50    0.93    --  101.00 -42.00-180.00   50
118  ω     77.00 127.00   0.50    0.93    --  101.00  77.00  60.00  100
119  ω    120.00 156.00   0.50    0.93    --  101.00  77.00 -60.00   72
120  ω    124.00 155.00   0.50    0.93    --  101.00  59.00  30.00   62
121  ω     71.00 107.00   0.50    0.93    --  101.00 -25.00  90.00   72
122  ω     77.00 151.00   0.50    0.93    --  101.00  77.00  90.00  148
123  ω     85.00 121.00   0.50    0.93    --  101.00  59.00 -90.00   72
124  ω    123.00 150.00   0.50    0.93    --  101.00  77.00-150.00   54
125  ω    132.00 157.00   0.50    0.93    --  101.00  77.00  30.00   50
126  ω     76.00 117.00   0.50    0.93    --  101.00  77.00-150.00   82
127  ω     78.00 105.00   0.50    0.93    --  101.00  77.00 -60.00   54
128  ω    124.00 150.00   0.50    0.93    --  101.00  77.00-180.00   52
129  ω     76.00 102.00   0.50    0.93    --  101.00  77.00  30.00   52
130  ω     76.00 102.00   0.50    0.93    --  101.00  77.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0611597000
_diffrn_orient_matrix_UB_12      -0.1308664000
_diffrn_orient_matrix_UB_13      0.0812643000
_diffrn_orient_matrix_UB_21      -0.0996670000
_diffrn_orient_matrix_UB_22      0.0155631000
_diffrn_orient_matrix_UB_23      -0.1144994000
_diffrn_orient_matrix_UB_31      0.1325935000
_diffrn_orient_matrix_UB_32      -0.0960935000
_diffrn_orient_matrix_UB_33      -0.0454875000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3123
_reflns_number_total             3653
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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         0.754
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3653
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.072
_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)+(0.0700P)²+0.3791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1375
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C23(H23), C11(H11), C19(H19), C22(H22), C21(H21), C12(H12),
 C15(H15), C20(H20), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_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
F3 F 0.96602(13) 0.14101(11) 0.32421(11) 0.0447(3) Uani 1 1 d . . . . .
F1 F 0.84426(13) 0.24451(11) 0.14320(9) 0.0428(3) Uani 1 1 d . . . . .
F2 F 0.80636(14) 0.04269(10) 0.26820(10) 0.0436(3) Uani 1 1 d . . . . .
C4 C 0.70444(18) 0.36987(16) 0.47736(15) 0.0292(3) Uani 1 1 d . . . . .
C5 C 0.74720(19) 0.36737(16) 0.35558(15) 0.0290(3) Uani 1 1 d . . . . .
C9 C 0.73345(19) 0.47530(16) 0.51937(15) 0.0310(4) Uani 1 1 d . . . . .
H9 H 0.7034 0.4768 0.6026 0.037 Uiso 1 1 calc R . . . .
C18 C 0.65596(19) 0.18760(16) 0.69085(15) 0.0291(3) Uani 1 1 d . . . . .
C3 C 0.6257(2) 0.24965(17) 0.54726(15) 0.0310(4) Uani 1 1 d . . . . .
H3 H 0.5125 0.2855 0.5321 0.037 Uiso 1 1 calc R . . . .
C8 C 0.8065(2) 0.57850(17) 0.43926(16) 0.0330(4) Uani 1 1 d . . . . .
C1 C 0.7005(2) 0.24345(17) 0.33254(15) 0.0310(4) Uani 1 1 d . . . . .
C6 C 0.8196(2) 0.46959(17) 0.27431(16) 0.0322(4) Uani 1 1 d . . . . .
H6 H 0.8482 0.4678 0.1909 0.039 Uiso 1 1 calc R . . . .
C10 C 0.5483(2) 0.28811(18) 0.25574(15) 0.0332(4) Uani 1 1 d . . . . .
C23 C 0.8023(2) 0.12033(18) 0.74028(17) 0.0350(4) Uani 1 1 d . . . . .
H23 H 0.8852 0.1111 0.6838 0.042 Uiso 1 1 calc R . . . .
C2 C 0.6834(2) 0.14616(17) 0.47268(15) 0.0342(4) Uani 1 1 d . . . . .
H2A H 0.6084 0.0873 0.4766 0.041 Uiso 1 1 calc R . . . .
H2B H 0.7832 0.0832 0.5079 0.041 Uiso 1 1 calc R . . . .
C24 C 0.8288(2) 0.16874(18) 0.26693(16) 0.0363(4) Uani 1 1 d . . . . .
C7 C 0.8501(2) 0.57551(17) 0.31604(16) 0.0339(4) Uani 1 1 d . . . . .
C11 C 0.4702(2) 0.1862(2) 0.25182(17) 0.0389(4) Uani 1 1 d . . . . .
H11 H 0.5133 0.0887 0.2940 0.047 Uiso 1 1 calc R . . . .
C19 C 0.5372(2) 0.20201(19) 0.77488(17) 0.0390(4) Uani 1 1 d . . . . .
H19 H 0.4362 0.2480 0.7422 0.047 Uiso 1 1 calc R . . . .
C22 C 0.8289(2) 0.0662(2) 0.87190(17) 0.0415(4) Uani 1 1 d . . . . .
H22 H 0.9293 0.0183 0.9048 0.050 Uiso 1 1 calc R . . . .
C17 C 0.8351(2) 0.69323(19) 0.48568(19) 0.0414(4) Uani 1 1 d . . . . .
H17A H 0.7777 0.7856 0.4312 0.062 Uiso 1 1 calc GR . . . .
H17B H 0.9450 0.6927 0.4815 0.062 Uiso 1 1 calc GR . . . .
H17C H 0.8012 0.6758 0.5744 0.062 Uiso 1 1 calc GR . . . .
C21 C 0.7105(3) 0.0814(2) 0.95484(17) 0.0446(5) Uani 1 1 d . . . . .
H21 H 0.7294 0.0450 1.0447 0.054 Uiso 1 1 calc R . . . .
C12 C 0.3304(2) 0.2256(2) 0.18694(18) 0.0462(5) Uani 1 1 d . . . . .
H12 H 0.2789 0.1552 0.1844 0.055 Uiso 1 1 calc R . . . .
C15 C 0.4816(2) 0.4311(2) 0.19310(17) 0.0418(4) Uani 1 1 d . . . . .
H15 H 0.5330 0.5019 0.1946 0.050 Uiso 1 1 calc R . . . .
C20 C 0.5640(3) 0.1499(2) 0.90679(19) 0.0469(5) Uani 1 1 d . . . . .
H20 H 0.4820 0.1614 0.9635 0.056 Uiso 1 1 calc R . . . .
C13 C 0.2661(2) 0.3678(3) 0.12580(19) 0.0512(5) Uani 1 1 d . . . . .
H13 H 0.1703 0.3946 0.0818 0.061 Uiso 1 1 calc R . . . .
C16 C 0.9276(3) 0.6859(2) 0.22832(19) 0.0468(5) Uani 1 1 d . . . . .
H16A H 0.8634 0.7801 0.2171 0.070 Uiso 1 1 calc GR . . . .
H16B H 0.9430 0.6719 0.1450 0.070 Uiso 1 1 calc GR . . . .
H16C H 1.0272 0.6779 0.2655 0.070 Uiso 1 1 calc GR . . . .
C14 C 0.3411(2) 0.4709(2) 0.12870(19) 0.0506(5) Uani 1 1 d . . . . .
H14 H 0.2969 0.5682 0.0869 0.061 Uiso 1 1 calc R . . . .


_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
F3 C24 1.345(2) . ?
F1 C24 1.346(2) . ?
F2 C24 1.3514(19) . ?
C4 C5 1.389(2) . ?
C4 C9 1.395(2) . ?
C4 C3 1.517(2) . ?
C5 C1 1.530(2) . ?
C5 C6 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.395(2) . ?
C18 C3 1.518(2) . ?
C18 C23 1.384(2) . ?
C18 C19 1.386(3) . ?
C3 H3 1.0000 . ?
C3 C2 1.543(2) . ?
C8 C7 1.407(3) . ?
C8 C17 1.513(2) . ?
C1 C10 1.545(2) . ?
C1 C2 1.558(2) . ?
C1 C24 1.521(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.403(2) . ?
C10 C11 1.398(2) . ?
C10 C15 1.402(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.390(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C7 C16 1.496(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.376(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C20 1.383(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.392(3) . ?
C20 H20 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.387(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C4 C9 120.32(15) . . ?
C5 C4 C3 110.88(14) . . ?
C9 C4 C3 128.79(15) . . ?
C4 C5 C1 109.99(14) . . ?
C4 C5 C6 120.41(15) . . ?
C6 C5 C1 129.59(15) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 120.06(15) . . ?
C8 C9 H9 120.0 . . ?
C23 C18 C3 121.09(15) . . ?
C23 C18 C19 118.80(15) . . ?
C19 C18 C3 120.08(15) . . ?
C4 C3 C18 114.84(13) . . ?
C4 C3 H3 108.3 . . ?
C4 C3 C2 101.45(13) . . ?
C18 C3 H3 108.3 . . ?
C18 C3 C2 115.21(13) . . ?
C2 C3 H3 108.3 . . ?
C9 C8 C7 119.51(15) . . ?
C9 C8 C17 119.36(16) . . ?
C7 C8 C17 121.12(16) . . ?
C5 C1 C10 112.96(13) . . ?
C5 C1 C2 101.07(12) . . ?
C10 C1 C2 111.37(14) . . ?
C24 C1 C5 110.38(14) . . ?
C24 C1 C10 110.68(13) . . ?
C24 C1 C2 110.03(14) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.67(16) . . ?
C7 C6 H6 120.2 . . ?
C11 C10 C1 120.40(15) . . ?
C11 C10 C15 118.27(16) . . ?
C15 C10 C1 121.27(15) . . ?
C18 C23 H23 119.7 . . ?
C18 C23 C22 120.51(18) . . ?
C22 C23 H23 119.7 . . ?
C3 C2 C1 104.53(12) . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
F3 C24 F1 106.57(15) . . ?
F3 C24 F2 106.02(13) . . ?
F3 C24 C1 112.20(13) . . ?
F1 C24 F2 106.26(13) . . ?
F1 C24 C1 112.96(14) . . ?
F2 C24 C1 112.34(15) . . ?
C8 C7 C16 120.33(15) . . ?
C6 C7 C8 120.02(15) . . ?
C6 C7 C16 119.65(16) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.86(18) . . ?
C12 C11 H11 119.6 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.77(18) . . ?
C20 C19 H19 119.6 . . ?
C23 C22 H22 119.8 . . ?
C21 C22 C23 120.40(18) . . ?
C21 C22 H22 119.8 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 C21 H21 120.1 . . ?
C22 C21 C20 119.73(17) . . ?
C20 C21 H21 120.1 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.97(18) . . ?
C13 C12 H12 120.0 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 120.97(18) . . ?
C14 C15 H15 119.5 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.77(18) . . ?
C21 C20 H20 120.1 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.23(18) . . ?
C14 C13 H13 119.9 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C14 H14 120.2 . . ?
C13 C14 C15 119.7(2) . . ?
C13 C14 H14 120.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.384
_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_7072-9921_emt048
_database_code_depnum_ccdc_archive 'CCDC 1875114'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 Cl F3 O2'
_chemical_formula_sum            'C24 H20 Cl F3 O2'
_chemical_formula_weight         432.85
_chemical_melting_point          ?
_chemical_oxdiff_formula         'F3 C20'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.0216(4)
_cell_length_b                   9.9831(4)
_cell_length_c                   11.9107(5)
_cell_angle_alpha                77.527(4)
_cell_angle_beta                 82.086(4)
_cell_angle_gamma                74.544(4)
_cell_volume                     1005.86(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5511
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.6870
_cell_measurement_theta_min      3.7860
_shelx_estimated_absorpt_T_max   0.563
_shelx_estimated_absorpt_T_min   0.415
_exptl_absorpt_coefficient_mu    2.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95456
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9416
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_min         3.815
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00 -56.00   0.50    0.20    --  -41.22 112.00 164.00   50
  2  ω    -19.00   8.00   0.50    0.20    --  -41.22 112.00 164.00   54
  3  ω    -48.00 -21.00   0.50    0.20    --  -41.22 112.00 164.00   54
  4  ω     93.00 142.00   0.50    0.20    --  101.00 112.00 164.00   98
  5  ω   -101.00 -30.00   0.50    0.20    --  -41.22 -43.00  90.00  142
  6  ω   -102.00 -61.00   0.50    0.20    --  -41.22 -65.00   0.00   82
  7  ω    -54.00 -23.00   0.50    0.20    --  -41.22 -65.00   0.00   62
  8  ω    -91.00 -16.00   0.50    0.20    --  -41.22 -77.00  60.00  150
  9  ω    -83.00 -50.00   0.50    0.20    --  -41.22 138.00  60.00   66
 10  ω   -102.00 -33.00   0.50    0.20    --  -41.22 -32.00-150.00  138
 11  ω    -38.00  20.00   0.50    0.20    --  -41.22  43.00-150.00  116
 12  ω     12.00  97.00   0.50    0.20    --   41.22-138.00   0.00  170
 13  ω      0.00  26.00   0.50    0.20    --   41.22 -21.00 -90.00   52
 14  ω     25.00  59.00   0.50    0.20    --   41.22 -65.00-150.00   68
 15  ω    -18.00   7.00   0.50    0.20    --   41.22 -65.00-150.00   50
 16  ω     58.00  87.00   0.50    0.20    --   41.22-138.00  60.00   58
 17  ω     -6.00  21.00   0.50    0.20    --   41.22-112.00  70.00   54
 18  ω     43.00  68.00   0.50    0.20    --   41.22-112.00  70.00   50
 19  ω     18.00  53.00   0.50    0.20    --   41.22 -43.00  60.00   70
 20  ω      5.00  39.00   0.50    0.20    --   41.22 -32.00 -60.00   68
 21  ω     61.00 104.00   0.50    0.20    --   41.22  32.00 -60.00   86
 22  ω    -11.00  15.00   0.50    0.20    --   41.22 -43.00  60.00   52
 23  ω     93.00 153.00   0.50    0.20    --  101.00  33.00 120.00  120
 24  ω     36.00  88.00   0.50    0.20    --  101.00-111.00-150.00  104
 25  ω     61.00 127.00   0.50    0.20    --  101.00 -77.00-150.00  132
 26  ω     72.00 121.00   0.50    0.20    --  101.00-133.00-150.00   98
 27  ω    127.00 153.00   0.50    0.20    --  101.00  77.00 150.00   52
 28  ω     81.00 155.00   0.50    0.20    --  101.00  68.00-150.00  148
 29  ω     39.00 113.00   0.50    0.20    --  101.00 -42.00  30.00  148
 30  ω     77.00 102.00   0.50    0.20    --  101.00  77.00 150.00   50
 31  ω     45.00  71.00   0.50    0.20    --  101.00 -77.00 -90.00   52
 32  ω     79.00 115.00   0.50    0.20    --  101.00 -77.00 -90.00   72
 33  ω    101.00 155.00   0.50    0.20    --  101.00  33.00 -90.00  108
 34  ω     94.00 130.00   0.50    0.20    --  101.00  42.00 150.00   72
 35  ω     89.00 115.00   0.50    0.20    --  101.00-111.00 -30.00   52
 36  ω    118.00 144.00   0.50    0.20    --  101.00 133.00 120.00   52
 37  ω     42.00  67.00   0.50    0.20    --  101.00-111.00 -30.00   50
 38  ω     87.00 112.00   0.50    0.20    --  101.00-111.00  90.00   50
 39  ω     38.00  93.00   0.50    0.20    --  101.00 -77.00  90.00  110
 40  ω     75.00 109.00   0.50    0.20    --  101.00 -33.00-180.00   68
 41  ω     35.00  83.00   0.50    0.20    --  101.00-111.00  90.00   96
 42  ω     86.00 156.00   0.50    0.20    --  101.00  68.00 -30.00  140
 43  ω     75.00 122.00   0.50    0.20    --  101.00 -68.00  30.00   94
 44  ω     35.00 114.00   0.50    0.20    --  101.00-111.00-120.00  158
 45  ω     92.00 141.00   0.50    0.20    --  101.00  17.00  90.00   98
 46  ω     40.00 113.00   0.50    0.20    --  101.00 -42.00 -90.00  146
 47  ω     64.00 116.00   0.50    0.20    --  101.00 -59.00 -60.00  104
 48  ω     96.00 145.00   0.50    0.20    --  101.00  33.00-180.00   98
 49  ω     46.00 113.00   0.50    0.20    --  101.00 -50.00 150.00  134
 50  ω     97.00 141.00   0.50    0.20    --  101.00 178.00 120.00   88
 51  ω     93.00 146.00   0.50    0.20    --  101.00  33.00 -30.00  106
 52  ω     95.00 120.00   0.50    0.20    --  101.00  33.00 -60.00   50
 53  ω     40.00  65.00   0.50    0.20    --  101.00 -33.00-180.00   50
 54  ω     75.00  97.50   0.50    0.20    --  101.00-112.00  70.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1492724000
_diffrn_orient_matrix_UB_12      -0.0341266000
_diffrn_orient_matrix_UB_13      0.0608937000
_diffrn_orient_matrix_UB_21      0.0864694000
_diffrn_orient_matrix_UB_22      0.0519899000
_diffrn_orient_matrix_UB_23      -0.1151728000
_diffrn_orient_matrix_UB_31      -0.0431229000
_diffrn_orient_matrix_UB_32      0.1506791000
_diffrn_orient_matrix_UB_33      0.0265195000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3457
_reflns_number_total             3799
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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         0.938
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.052
_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)+(0.0453P)²+0.6162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1008
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C9(H9), C6(H6), C13(H13), C16(H16), C21(H21), C22(H22), C14(H14),
 C15(H15), C19(H19), C18(H18)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.06513(6) 0.95828(5) 0.81637(4) 0.03704(14) Uani 1 1 d . . . . .
F3 F 0.37326(12) 0.89314(10) 0.02532(9) 0.0297(2) Uani 1 1 d . . . . .
F1 F 0.19135(11) 0.78898(11) 0.09694(9) 0.0282(2) Uani 1 1 d . . . . .
F2 F 0.39224(12) 0.68002(11) 0.00276(8) 0.0266(2) Uani 1 1 d . . . . .
O1 O 0.18616(14) 0.28344(13) 0.49751(10) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.24654(14) 0.25292(13) 0.28588(10) 0.0250(3) Uani 1 1 d . . . . .
C10 C 0.36148(18) 0.58655(17) 0.26318(14) 0.0189(3) Uani 1 1 d . . . . .
C11 C 0.60099(19) 0.66885(17) 0.16387(13) 0.0197(3) Uani 1 1 d . . . . .
C12 C 0.68011(19) 0.77495(18) 0.11843(14) 0.0209(3) Uani 1 1 d . . . . .
H12 H 0.6241 0.8712 0.1035 0.025 Uiso 1 1 calc R . . . .
C9 C 0.33401(19) 0.47123(17) 0.22731(14) 0.0203(3) Uani 1 1 d . . . . .
H9 H 0.3542 0.4616 0.1487 0.024 Uiso 1 1 calc R . . . .
C17 C 0.30349(19) 0.79591(17) 0.49468(14) 0.0209(3) Uani 1 1 d . . . . .
C6 C 0.27805(19) 0.49960(18) 0.46065(14) 0.0214(3) Uani 1 1 d . . . . .
H6 H 0.2607 0.5088 0.5394 0.026 Uiso 1 1 calc R . . . .
C8 C 0.27656(18) 0.37131(17) 0.30918(14) 0.0199(3) Uani 1 1 d . . . . .
C7 C 0.24544(19) 0.38705(17) 0.42591(14) 0.0207(3) Uani 1 1 d . . . . .
C13 C 0.8395(2) 0.74056(19) 0.09516(14) 0.0236(4) Uani 1 1 d . . . . .
H13 H 0.8916 0.8133 0.0641 0.028 Uiso 1 1 calc R . . . .
C2 C 0.42442(19) 0.70906(17) 0.19137(14) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.33691(19) 0.59916(17) 0.37776(14) 0.0204(3) Uani 1 1 d . . . . .
C16 C 0.6863(2) 0.52860(18) 0.18538(15) 0.0244(4) Uani 1 1 d . . . . .
H16 H 0.6350 0.4553 0.2164 0.029 Uiso 1 1 calc R . . . .
C21 C 0.0718(2) 0.86147(18) 0.62047(15) 0.0253(4) Uani 1 1 d . . . . .
H21 H -0.0357 0.8699 0.6391 0.030 Uiso 1 1 calc R . . . .
C22 C 0.1458(2) 0.80937(18) 0.52333(15) 0.0241(4) Uani 1 1 d . . . . .
H22 H 0.0877 0.7822 0.4751 0.029 Uiso 1 1 calc R . . . .
C14 C 0.9228(2) 0.60075(19) 0.11698(15) 0.0257(4) Uani 1 1 d . . . . .
H14 H 1.0318 0.5775 0.1013 0.031 Uiso 1 1 calc R . . . .
C1 C 0.34568(19) 0.76732(18) 0.07962(14) 0.0222(3) Uani 1 1 d . . . . .
C23 C 0.1407(2) 0.3024(2) 0.61436(14) 0.0260(4) Uani 1 1 d . . . . .
H23A H 0.0622 0.3916 0.6150 0.039 Uiso 1 1 calc GR . . . .
H23B H 0.2308 0.3048 0.6507 0.039 Uiso 1 1 calc GR . . . .
H23C H 0.0980 0.2237 0.6572 0.039 Uiso 1 1 calc GR . . . .
C4 C 0.3874(2) 0.72682(18) 0.39502(15) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.4994 0.6945 0.4087 0.028 Uiso 1 1 calc R . . . .
C3 C 0.3749(2) 0.81863(17) 0.27386(14) 0.0218(3) Uani 1 1 d . . . . .
H3A H 0.4448 0.8831 0.2595 0.026 Uiso 1 1 calc R . . . .
H3B H 0.2678 0.8755 0.2637 0.026 Uiso 1 1 calc R . . . .
C15 C 0.8460(2) 0.49499(19) 0.16180(16) 0.0281(4) Uani 1 1 d . . . . .
H15 H 0.9028 0.3990 0.1765 0.034 Uiso 1 1 calc R . . . .
C19 C 0.3128(2) 0.89450(19) 0.66210(16) 0.0293(4) Uani 1 1 d . . . . .
H19 H 0.3691 0.9253 0.7091 0.035 Uiso 1 1 calc R . . . .
C18 C 0.3852(2) 0.84208(18) 0.56403(16) 0.0261(4) Uani 1 1 d . . . . .
H18 H 0.4918 0.8376 0.5440 0.031 Uiso 1 1 calc R . . . .
C20 C 0.1572(2) 0.90097(18) 0.68996(15) 0.0254(4) Uani 1 1 d . . . . .
C24 C 0.2746(2) 0.23431(19) 0.16857(15) 0.0268(4) Uani 1 1 d . . . . .
H24A H 0.2151 0.3176 0.1194 0.040 Uiso 1 1 calc GR . . . .
H24B H 0.2430 0.1500 0.1616 0.040 Uiso 1 1 calc GR . . . .
H24C H 0.3848 0.2226 0.1442 0.040 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
Cl1 C20 1.7489(18) . ?
F3 C1 1.3526(19) . ?
F1 C1 1.3444(19) . ?
F2 C1 1.348(2) . ?
O1 C7 1.3680(19) . ?
O1 C23 1.434(2) . ?
O2 C8 1.3711(19) . ?
O2 C24 1.429(2) . ?
C10 C9 1.401(2) . ?
C10 C2 1.528(2) . ?
C10 C5 1.380(2) . ?
C11 C12 1.405(2) . ?
C11 C2 1.542(2) . ?
C11 C16 1.394(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.390(2) . ?
C17 C22 1.394(2) . ?
C17 C4 1.512(2) . ?
C17 C18 1.397(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(2) . ?
C6 C5 1.399(2) . ?
C8 C7 1.414(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C2 C1 1.523(2) . ?
C2 C3 1.563(2) . ?
C5 C4 1.524(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.393(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(2) . ?
C21 C20 1.383(3) . ?
C22 H22 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.387(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C4 H4 1.0000 . ?
C4 C3 1.534(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C15 H15 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.392(3) . ?
C19 C20 1.384(3) . ?
C18 H18 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C7 O1 C23 116.32(13) . . ?
C8 O2 C24 116.79(12) . . ?
C9 C10 C2 128.84(14) . . ?
C5 C10 C9 121.08(14) . . ?
C5 C10 C2 110.04(14) . . ?
C12 C11 C2 120.01(15) . . ?
C16 C11 C12 118.40(15) . . ?
C16 C11 C2 121.58(14) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.67(16) . . ?
C13 C12 H12 119.7 . . ?
C10 C9 H9 120.7 . . ?
C8 C9 C10 118.60(15) . . ?
C8 C9 H9 120.7 . . ?
C22 C17 C4 121.58(15) . . ?
C22 C17 C18 118.28(15) . . ?
C18 C17 C4 120.08(15) . . ?
C7 C6 H6 120.5 . . ?
C7 C6 C5 118.95(15) . . ?
C5 C6 H6 120.5 . . ?
O2 C8 C9 124.46(15) . . ?
O2 C8 C7 115.15(14) . . ?
C9 C8 C7 120.39(15) . . ?
O1 C7 C6 124.97(15) . . ?
O1 C7 C8 114.79(14) . . ?
C6 C7 C8 120.22(15) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.32(15) . . ?
C14 C13 H13 119.8 . . ?
C10 C2 C11 113.16(13) . . ?
C10 C2 C3 100.87(12) . . ?
C11 C2 C3 111.59(13) . . ?
C1 C2 C10 110.72(13) . . ?
C1 C2 C11 109.70(13) . . ?
C1 C2 C3 110.55(13) . . ?
C10 C5 C6 120.67(15) . . ?
C10 C5 C4 110.62(14) . . ?
C6 C5 C4 128.67(15) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.58(16) . . ?
C15 C16 H16 119.7 . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C20 C21 C22 118.83(16) . . ?
C17 C22 H22 119.3 . . ?
C21 C22 C17 121.44(16) . . ?
C21 C22 H22 119.3 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.57(16) . . ?
C15 C14 H14 120.2 . . ?
F3 C1 C2 112.56(13) . . ?
F1 C1 F3 106.06(13) . . ?
F1 C1 F2 106.31(13) . . ?
F1 C1 C2 112.45(13) . . ?
F2 C1 F3 106.27(13) . . ?
F2 C1 C2 112.67(14) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C4 C5 116.13(14) . . ?
C17 C4 H4 107.4 . . ?
C17 C4 C3 116.89(14) . . ?
C5 C4 H4 107.4 . . ?
C5 C4 C3 100.91(13) . . ?
C3 C4 H4 107.4 . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 C2 103.99(13) . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.46(17) . . ?
C14 C15 H15 119.8 . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C20 C19 C18 118.85(16) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.00(16) . . ?
C19 C18 H18 119.5 . . ?
C21 C20 Cl1 118.58(14) . . ?
C21 C20 C19 121.50(16) . . ?
C19 C20 Cl1 119.92(14) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 1.119
_oxdiff_exptl_absorpt_empirical_full_min 0.927
####################################################################### 
# 
# 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_7072-9949_emt002
_database_code_depnum_ccdc_archive 'CCDC 1875113'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 F3'
_chemical_formula_sum            'C25 H23 F3'
_chemical_formula_weight         380.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 F3'
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'
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                   10.5544(4)
_cell_length_b                   15.4584(6)
_cell_length_c                   12.2743(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.702(4)
_cell_angle_gamma                90
_cell_volume                     1953.59(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5028
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.2380
_cell_measurement_theta_min      3.1280
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18127
_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         27.499
_diffrn_reflns_theta_min         2.635
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -80.00   21.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  -19.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00   45.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -77.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega   38.00  100.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       24.2996  178.0000 -120.0000 62

#__ type_ start__ end____ width___ exp.time_
  4 omega  -79.00   -9.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  -57.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00   -3.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  -57.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega  -35.00   42.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3621   38.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
  7 omega  -36.00   -1.00   1.0000   26.0000
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -38.0000  -30.0000 35
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0132015000
_diffrn_orient_matrix_UB_12      0.0423542000
_diffrn_orient_matrix_UB_13      -0.0217486000
_diffrn_orient_matrix_UB_21      -0.0651967000
_diffrn_orient_matrix_UB_22      -0.0038414000
_diffrn_orient_matrix_UB_23      0.0057074000
_diffrn_orient_matrix_UB_31      0.0179212000
_diffrn_orient_matrix_UB_32      0.0172283000
_diffrn_orient_matrix_UB_33      0.0548009000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3834
_reflns_number_total             4490
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.032
_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)+(0.0405P)²+0.8642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0984
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C18(H18), C15(H15), C22(H22), C8(H8), C13(H13), C14(H14),
 C20(H20), C19(H19), C21(H21)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F2 F 0.11238(8) 0.43304(5) 0.16463(6) 0.02564(19) Uani 1 1 d . . . . .
F3 F 0.20859(7) 0.35397(5) 0.06342(6) 0.02385(18) Uani 1 1 d . . . . .
F1 F 0.32061(8) 0.43483(5) 0.19168(6) 0.02709(19) Uani 1 1 d . . . . .
C1 C 0.21681(12) 0.38216(8) 0.16867(10) 0.0193(3) Uani 1 1 d . . . . .
C17 C 0.55185(12) 0.22899(8) 0.41098(10) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.25144(12) 0.34723(7) 0.37052(9) 0.0159(2) Uani 1 1 d . . . . .
C5 C 0.38349(12) 0.34684(7) 0.42204(10) 0.0160(2) Uani 1 1 d . . . . .
C11 C 0.11682(12) 0.24399(8) 0.22694(10) 0.0168(2) Uani 1 1 d . . . . .
C4 C 0.46490(11) 0.30078(8) 0.35194(10) 0.0166(2) Uani 1 1 d . . . . .
H4 H 0.5188 0.3442 0.3221 0.020 Uiso 1 1 calc R . . . .
C2 C 0.22950(12) 0.30844(8) 0.25285(9) 0.0156(2) Uani 1 1 d . . . . .
C7 C 0.33818(13) 0.42209(8) 0.57997(10) 0.0198(3) Uani 1 1 d . . . . .
C6 C 0.42980(12) 0.38623(7) 0.52576(10) 0.0179(2) Uani 1 1 d . . . . .
C3 C 0.36142(12) 0.26281(8) 0.25429(10) 0.0173(2) Uani 1 1 d . . . . .
H3A H 0.3530 0.1997 0.2646 0.021 Uiso 1 1 calc R . . . .
H3B H 0.3875 0.2727 0.1826 0.021 Uiso 1 1 calc R . . . .
C9 C 0.15897(12) 0.38162(8) 0.42449(10) 0.0188(3) Uani 1 1 d . . . . .
C12 C 0.12326(12) 0.17402(8) 0.30012(10) 0.0199(3) Uani 1 1 d . . . . .
H12 H 0.1955 0.1691 0.3616 0.024 Uiso 1 1 calc R . . . .
C16 C 0.00917(12) 0.24996(9) 0.13866(10) 0.0217(3) Uani 1 1 d . . . . .
H16 H 0.0022 0.2969 0.0877 0.026 Uiso 1 1 calc R . . . .
C18 C 0.67055(13) 0.21107(10) 0.38429(11) 0.0254(3) Uani 1 1 d . . . . .
H18 H 0.7007 0.2466 0.3321 0.031 Uiso 1 1 calc R . . . .
C15 C -0.08834(13) 0.18784(10) 0.12429(11) 0.0269(3) Uani 1 1 d . . . . .
H15 H -0.1618 0.1933 0.0641 0.032 Uiso 1 1 calc R . . . .
C22 C 0.51006(13) 0.17543(9) 0.48719(11) 0.0225(3) Uani 1 1 d . . . . .
H22 H 0.4286 0.1862 0.5056 0.027 Uiso 1 1 calc R . . . .
C23 C 0.57344(13) 0.39095(9) 0.57735(11) 0.0235(3) Uani 1 1 d . . . . .
H23A H 0.5960 0.3469 0.6358 0.035 Uiso 1 1 calc GR . . . .
H23B H 0.5947 0.4484 0.6101 0.035 Uiso 1 1 calc GR . . . .
H23C H 0.6228 0.3806 0.5197 0.035 Uiso 1 1 calc GR . . . .
C8 C 0.20648(13) 0.41749(8) 0.52981(10) 0.0208(3) Uani 1 1 d . . . . .
H8 H 0.1459 0.4400 0.5694 0.025 Uiso 1 1 calc R . . . .
C13 C 0.02676(13) 0.11177(9) 0.28500(11) 0.0247(3) Uani 1 1 d . . . . .
H13 H 0.0337 0.0645 0.3355 0.030 Uiso 1 1 calc R . . . .
C24 C 0.38077(15) 0.46696(9) 0.69148(11) 0.0268(3) Uani 1 1 d . . . . .
H24A H 0.4405 0.4293 0.7430 0.040 Uiso 1 1 calc GR . . . .
H24B H 0.3046 0.4794 0.7223 0.040 Uiso 1 1 calc GR . . . .
H24C H 0.4249 0.5212 0.6814 0.040 Uiso 1 1 calc GR . . . .
C25 C 0.01410(13) 0.38011(9) 0.37765(11) 0.0251(3) Uani 1 1 d . . . . .
H25A H -0.0052 0.4069 0.3035 0.038 Uiso 1 1 calc GR . . . .
H25B H -0.0299 0.4124 0.4274 0.038 Uiso 1 1 calc GR . . . .
H25C H -0.0166 0.3201 0.3717 0.038 Uiso 1 1 calc GR . . . .
C14 C -0.08008(13) 0.11817(9) 0.19632(12) 0.0270(3) Uani 1 1 d . . . . .
H14 H -0.1464 0.0755 0.1853 0.032 Uiso 1 1 calc R . . . .
C20 C 0.70354(16) 0.08947(10) 0.50964(13) 0.0369(4) Uani 1 1 d . . . . .
H20 H 0.7553 0.0423 0.5433 0.044 Uiso 1 1 calc R . . . .
C19 C 0.74563(14) 0.14128(11) 0.43365(13) 0.0346(4) Uani 1 1 d . . . . .
H19 H 0.8264 0.1295 0.4146 0.042 Uiso 1 1 calc R . . . .
C21 C 0.58553(16) 0.10637(9) 0.53687(12) 0.0316(3) Uani 1 1 d . . . . .
H21 H 0.5561 0.0708 0.5894 0.038 Uiso 1 1 calc R . . . .


_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
F2 C1 1.3460(15) . ?
F3 C1 1.3480(14) . ?
F1 C1 1.3442(15) . ?
C1 C2 1.5242(17) . ?
C17 C4 1.5187(17) . ?
C17 C18 1.3907(18) . ?
C17 C22 1.3917(18) . ?
C10 C5 1.3981(17) . ?
C10 C2 1.5337(16) . ?
C10 C9 1.3994(17) . ?
C5 C4 1.5201(17) . ?
C5 C6 1.3989(16) . ?
C11 C2 1.5304(17) . ?
C11 C12 1.3980(17) . ?
C11 C16 1.3900(17) . ?
C4 C3 1.5486(16) . ?
C2 C3 1.5576(16) . ?
C7 C6 1.4029(18) . ?
C7 C8 1.3928(19) . ?
C7 C24 1.5119(17) . ?
C6 C23 1.5108(18) . ?
C9 C8 1.3946(17) . ?
C9 C25 1.5108(18) . ?
C12 C13 1.3838(18) . ?
C16 C15 1.3902(19) . ?
C18 C19 1.396(2) . ?
C15 C14 1.384(2) . ?
C22 C21 1.3901(19) . ?
C13 C14 1.3879(19) . ?
C20 C19 1.375(2) . ?
C20 C21 1.384(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 C1 F3 105.90(9) . . ?
F2 C1 C2 114.27(10) . . ?
F3 C1 C2 112.67(10) . . ?
F1 C1 F2 106.07(10) . . ?
F1 C1 F3 105.96(10) . . ?
F1 C1 C2 111.37(10) . . ?
C18 C17 C4 120.96(12) . . ?
C18 C17 C22 118.35(12) . . ?
C22 C17 C4 120.52(11) . . ?
C5 C10 C2 110.69(10) . . ?
C5 C10 C9 121.14(11) . . ?
C9 C10 C2 128.15(11) . . ?
C10 C5 C4 112.17(10) . . ?
C10 C5 C6 121.59(11) . . ?
C6 C5 C4 126.24(11) . . ?
C12 C11 C2 116.38(10) . . ?
C16 C11 C2 125.69(11) . . ?
C16 C11 C12 117.92(11) . . ?
C17 C4 C5 115.45(10) . . ?
C17 C4 C3 109.98(10) . . ?
C5 C4 C3 103.03(9) . . ?
C1 C2 C10 108.58(10) . . ?
C1 C2 C11 113.42(10) . . ?
C1 C2 C3 106.94(10) . . ?
C10 C2 C3 102.53(9) . . ?
C11 C2 C10 113.57(10) . . ?
C11 C2 C3 111.06(10) . . ?
C6 C7 C24 120.79(12) . . ?
C8 C7 C6 119.68(11) . . ?
C8 C7 C24 119.52(12) . . ?
C5 C6 C7 117.66(11) . . ?
C5 C6 C23 121.34(12) . . ?
C7 C6 C23 121.00(11) . . ?
C4 C3 C2 108.28(9) . . ?
C10 C9 C25 124.53(11) . . ?
C8 C9 C10 116.35(12) . . ?
C8 C9 C25 119.10(11) . . ?
C13 C12 C11 121.43(12) . . ?
C11 C16 C15 120.56(12) . . ?
C17 C18 C19 120.44(14) . . ?
C14 C15 C16 121.04(12) . . ?
C21 C22 C17 121.07(13) . . ?
C7 C8 C9 123.40(12) . . ?
C12 C13 C14 120.18(12) . . ?
C15 C14 C13 118.86(13) . . ?
C19 C20 C21 119.74(14) . . ?
C20 C19 C18 120.49(14) . . ?
C20 C21 C22 119.90(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_7072-9926_b-10a
_database_code_depnum_ccdc_archive 'CCDC 1875111'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 F3'
_chemical_formula_sum            'C24 H21 F3'
_chemical_formula_weight         366.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.6641(3)
_cell_length_b                   9.1396(2)
_cell_length_c                   17.3076(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.883(2)
_cell_angle_gamma                90
_cell_volume                     1835.36(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16756
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      71.8120
_cell_measurement_theta_min      4.3250
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.819
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39863
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.844
_diffrn_reflns_theta_min         4.371
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_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    -62.00 -36.00   0.50    1.00    --  -41.35  74.00-166.00   52
  2  ω    -92.00 -22.00   0.50    1.00    --  -41.35 -74.00  64.00  140
  3  ω    -13.00  14.00   0.50    1.00    --  -41.35  74.00-166.00   54
  4  ω     23.00  48.00   0.50    1.00    --   41.35 -74.00  64.00   50
  5  ω     37.00 123.00   0.50    4.00    --  101.00 -74.00  64.00  172
  6  ω     94.00 153.00   0.50    4.00    --  101.00  74.00-166.00  118
  7  ω    -57.00 -30.00   0.50    1.00    --  -41.35  11.00  60.00   54
  8  ω      4.00  30.00   0.50    1.00    --  -41.35  11.00  60.00   52
  9  ω   -100.00 -75.00   0.50    1.00    --  -41.35 -43.00 -30.00   50
 10  ω    -68.00 -29.00   0.50    1.00    --  -41.35 -43.00 -30.00   78
 11  ω    -96.00 -70.00   0.50    1.00    --  -41.35 -43.00  30.00   52
 12  ω     36.00  61.00   0.50    1.00    --   41.35  32.00 150.00   50
 13  ω     19.00  45.00   0.50    1.00    --   41.35  74.00-166.00   52
 14  ω     17.00  46.00   0.50    1.00    --   41.35  77.00  90.00   58
 15  ω    -22.00  10.00   0.50    1.00    --   41.35 -65.00 120.00   64
 16  ω     14.00  54.00   0.50    1.00    --   41.35 -65.00 120.00   80
 17  ω     73.00 104.00   0.50    1.00    --   41.35  65.00 -90.00   62
 18  ω     82.00 107.00   0.50    1.00    --   41.35  32.00 150.00   50
 19  ω     22.00  70.00   0.50    1.00    --   41.35  65.00 -90.00   96
 20  ω     72.00  98.00   0.50    1.00    --   41.35  74.00-166.00   52
 21  ω     75.00 100.00   0.50    1.00    --   41.35  77.00  90.00   50
 22  ω     86.00 112.00   0.50    4.00    --  101.00 -50.00  90.00   52
 23  ω     45.00  81.00   0.50    4.00    --  101.00 -50.00  90.00   72
 24  ω     44.00 107.00   0.50    4.00    --  101.00 -33.00  30.00  126
 25  ω     95.00 148.00   0.50    4.00    --  101.00  33.00  90.00  106
 26  ω     39.00 118.00   0.50    4.00    --  101.00 -68.00-120.00  158
 27  ω    114.00 147.00   0.50    4.00    --  101.00  33.00 120.00   66
 28  ω     77.00 104.00   0.50    4.00    --  101.00 -42.00-150.00   54
 29  ω     41.00  67.00   0.50    4.00    --  101.00 -42.00-150.00   52
 30  ω     92.00 134.00   0.50    4.00    --  101.00  33.00-180.00   84
 31  ω     41.00 101.00   0.50    4.00    --  101.00 -50.00 -60.00  120
 32  ω    111.00 154.00   0.50    4.00    --  101.00  93.00 150.00   86
 33  ω     84.00 130.00   0.50    4.00    --  101.00  68.00 120.00   92
 34  ω    127.00 152.00   0.50    4.00    --  101.00  17.00 -30.00   50
 35  ω     97.00 122.00   0.50    4.00    --  101.00  17.00 -30.00   50
 36  ω     58.00  84.00   0.50    4.00    --  101.00 -87.00 150.00   52
 37  ω    119.00 145.00   0.50    4.00    --  101.00  33.00-120.00   52
 38  ω    132.00 157.00   0.50    4.00    --  101.00  77.00-150.00   50
 39  ω    104.00 129.00   0.50    4.00    --  101.00 -87.00 150.00   50
 40  ω     77.00 116.00   0.50    4.00    --  101.00  77.00-150.00   78
 41  ω     81.00 107.00   0.50    4.00    --  101.00  93.00 150.00   52
 42  ω     48.00  75.00   0.50    1.00    --   41.35  77.00-180.00   54
 43  ω    -18.00   8.00   0.50    1.00    --  -41.35 104.00 120.00   52
 44  ω    -61.00 -26.00   0.50    1.00    --  -41.35 104.00 120.00   70
 45  ω    -59.00 -33.00   0.50    1.00    --  -41.35 -32.00-120.00   52
 46  ω    -19.00  12.00   0.50    1.00    --   41.35 -54.00-180.00   62
 47  ω     21.00  55.00   0.50    1.00    --   41.35 -54.00-180.00   68
 48  ω     70.00  96.00   0.50    1.00    --   41.35  54.00 -30.00   52
 49  ω    -23.00   3.00   0.50    1.00    --   41.35 -32.00-120.00   52
 50  ω     32.00  66.00   0.50    1.00    --   41.35  54.00 -30.00   68
 51  ω     77.00 104.00   0.50    1.00    --   41.35  43.00 120.00   54
 52  ω     -1.00  50.00   0.50    1.00    --   41.35 -32.00-150.00  102
 53  ω     48.00  74.00   0.50    4.00    --  101.00 -42.00 120.00   52
 54  ω     35.00  61.00   0.50    4.00    --  101.00 -25.00  60.00   52
 55  ω     28.00  54.00   0.50    4.00    --  101.00  -8.00-180.00   52
 56  ω     86.00 126.00   0.50    4.00    --  101.00  -8.00-180.00   80
 57  ω     89.00 114.00   0.50    4.00    --  101.00  17.00 150.00   50
 58  ω    118.00 151.00   0.50    4.00    --  101.00  68.00-120.00   66
 59  ω     39.00  94.00   0.50    4.00    --  101.00-111.00  90.00  110
 60  ω    125.00 151.00   0.50    4.00    --  101.00  50.00-180.00   52
 61  ω    131.00 157.00   0.50    4.00    --  101.00  68.00 -90.00   52
 62  ω     82.00 108.00   0.50    4.00    --  101.00  68.00-120.00   52
 63  ω     85.00 119.00   0.50    4.00    --  101.00  50.00-180.00   68
 64  ω     81.00 109.00   0.50    4.00    --  101.00-111.00 150.00   56
 65  ω     80.00 113.00   0.50    4.00    --  101.00  68.00 -90.00   66
 66  ω    132.00 157.00   0.50    4.00    --  101.00  17.00 150.00   50
 67  ω     53.00  79.00   0.50    4.00    --  101.00-111.00 150.00   52
 68  ω     71.00 110.00   0.50    4.00    --  101.00 -25.00  60.00   78
 69  ω     76.00 102.00   0.50    4.00    --  101.00  77.00 -90.00   52
 70  ω     88.00 117.00   0.50    4.00    --  101.00  50.00 -30.00   58
 71  ω     74.00 114.00   0.50    4.00    --  101.00 -68.00   0.00   80
 72  ω     80.00 128.00   0.50    4.00    --  101.00  68.00 -30.00   96
 73  ω     76.00 102.00   0.50    4.00    --  101.00  77.00 -60.00   52
 74  ω     81.00 107.00   0.50    4.00    --  101.00 -42.00 120.00   52
 75  ω    132.00 157.00   0.50    4.00    --  101.00  50.00 -30.00   50
 76  ω     84.00 133.00   0.50    4.00    --  101.00  59.00 -60.00   98
 77  ω     65.00 104.00   0.50    4.00    --  101.00 -25.00 -30.00   78
 78  ω     94.00 120.00   0.50    4.00    --  101.00  42.00 -60.00   52
 79  ω    120.00 146.00   0.50    4.00    --  101.00  50.00 -90.00   52
 80  ω     80.00 106.00   0.50    4.00    --  101.00  68.00 -60.00   52
 81  ω    125.00 150.00   0.50    4.00    --  101.00  68.00 -60.00   50
 82  ω     87.00 112.00   0.50    4.00    --  101.00  50.00 -90.00   50
 83  ω    -67.00 -41.00   0.50    1.00    --  -41.35  88.00  77.00   52
 84  ω    -87.00 -45.00   0.50    1.00    --  -41.35 138.00 -90.00   84
 85  ω    -38.00 -11.00   0.50    1.00    --  -41.35 138.00 -90.00   54
 86  ω     48.00  74.00   0.50    1.00    --   41.35-138.00  90.00   52
 87  ω     50.00  94.00   0.50    1.00    --   41.35-138.00   0.00   88
 88  ω     69.00  95.00   0.50    1.00    --   41.35  32.00-120.00   52
 89  ω     40.00  87.00   0.50    4.00    --  101.00-133.00  90.00   94
 90  ω     85.00 115.00   0.50    4.00    --  101.00-111.00 120.00   60
 91  ω     37.00  79.00   0.50    4.00    --  101.00-111.00  30.00   84
 92  ω     81.00 114.00   0.50    4.00    --  101.00-111.00 -30.00   66
 93  ω     71.00 124.00   0.50    4.00    --  101.00-133.00-120.00  106
 94  ω     40.00  65.00   0.50    4.00    --  101.00-133.00-120.00   50
 95  ω     98.00 123.00   0.50    4.00    --  101.00 -68.00-180.00   50
 96  ω    123.00 149.00   0.50    4.00    --  101.00  42.00   0.00   52
 97  ω     93.00 119.00   0.50    4.00    --  101.00-133.00  90.00   52
 98  ω     57.00  92.00   0.50    4.00    --  101.00-111.00-120.00   70
 99  ω     58.00  84.00   0.50    4.00    --  101.00 178.00 120.00   52
100  ω    118.00 143.00   0.50    4.00    --  101.00 178.00 120.00   50
101  ω     80.00 113.00   0.50    4.00    --  101.00-111.00 -90.00   66
102  ω     40.00  74.00   0.50    4.00    --  101.00-111.00 -90.00   68
103  ω     14.00  59.00   0.50    1.00    --   41.35 -88.00 -39.00   90
104  ω    -42.00 -17.00   0.50    1.00    --    4.00 122.00 177.40   50
105  ω    -37.00  -8.00   0.50    1.00    --    8.00 127.00  -3.35   58
106  ω    -11.00  14.00   0.50    1.00    --   24.00 102.00  27.49   50
107  ω    -43.00 -18.00   0.50    1.00    --   24.00 153.00 168.33   50
108  ω     -4.00  21.00   0.50    1.00    --   28.00  97.00 128.69   50
109  ω     -3.00  22.00   0.50    1.00    --   28.00  95.00-153.78   50
110  ω      3.00  28.00   0.50    1.00    --   32.00  89.00 -35.21   50
111  ω      3.00  28.00   0.50    1.00    --   32.00  89.00  41.70   50
112  ω      3.00  28.00   0.50    1.00    --   32.00  89.00 166.18   50
113  ω      2.00  27.00   0.50    1.00    --   32.00  91.00 102.88   50
114  ω      4.00  29.00   0.50    1.00    --   32.00  88.00 -93.05   50
115  ω      9.00  34.00   0.50    1.00    --   36.00  85.00 142.69   50
116  ω     14.00  39.00   0.50    1.00    --   40.00  82.00  -4.43   50
117  ω     15.00  40.00   0.50    1.00    --   40.00  80.00  27.24   50
118  ω     16.00  41.00   0.50    1.00    --   41.35  82.00-145.90   50
119  ω     19.00  44.00   0.50    1.00    --   44.00  80.00 -85.51   50
120  ω     18.00  43.00   0.50    1.00    --   44.00  82.00 179.21   50
121  ω     19.00  44.00   0.50    1.00    --   44.00  81.00 155.08   50
122  ω     19.00  44.00   0.50    1.00    --   44.00  80.00  86.43   50
123  ω     18.00  43.00   0.50    1.00    --   44.00  82.00 -57.57   50
124  ω     19.00  44.00   0.50    1.00    --   44.00  80.00  45.59   50
125  ω     18.00  43.00   0.50    1.00    --   44.00  82.00 123.27   50
126  ω     18.00  43.00   0.50    1.00    --   44.00  82.00-133.22   50
127  ω     28.00  54.00   0.50    1.00    --   52.00  75.00-166.26   52
128  ω     27.00  53.00   0.50    1.00    --   52.00  77.00 102.47   52
129  ω     28.00  56.00   0.50    1.00    --   52.00  76.00 144.67   56
130  ω     36.00  62.00   0.50    1.00    --   56.00  69.00 -33.53   52
131  ω     33.00  59.00   0.50    1.00    --   56.00  77.00  60.93   52
132  ω     31.00  57.00   0.50    1.00    --   56.00  77.00-133.04   52
133  ω     93.00 119.00   0.50    1.00    --   56.00  77.00-133.04   52
134  ω     33.00  59.00   0.50    1.00    --   56.00  74.00  14.27   52
135  ω     31.00  57.00   0.50    1.00    --   56.00  77.00 -89.42   52
136  ω     36.00  62.00   0.50    1.00    --   60.00  75.00  -2.42   52
137  ω     41.00  67.00   0.50    1.00    --   60.00  65.00  46.45   52
138  ω    100.00 125.00   0.50    1.00    --   60.00  77.00 176.37   50
139  ω     35.00  61.00   0.50    1.00    --   60.00  77.00 176.37   52
140  ω     43.00  69.00   0.50    1.00    --   60.00  65.00  97.75   52
141  ω     44.00  78.00   0.50    1.00    --   64.00  66.00   2.18   68
142  ω     96.00 122.00   0.50    1.00    --   64.00  66.00   2.18   52
143  ω     48.00  74.00   0.50    1.00    --   68.00  68.00-127.90   52
144  ω     47.00  83.00   0.50    1.00    --   68.00  68.00 107.69   72
145  ω     52.00  78.00   0.50    1.00    --   68.00  52.00 -23.15   52
146  ω    100.00 127.00   0.50    1.00    --   68.00  68.00-127.90   54
147  ω     52.00  81.00   0.50    4.00    --   72.00  70.00 -99.38   58
148  ω     49.00  75.00   0.50    4.00    --   72.00  72.00-121.77   52
149  ω     53.00  79.00   0.50    4.00    --   72.00  67.00 -64.51   52
150  ω     53.00  79.00   0.50    4.00    --   76.00  72.00-173.81   52
151  ω     52.00 100.00   0.50    4.00    --   76.00  75.00  53.88   96
152  ω     61.00  93.00   0.50    4.00    --   76.00  50.00  -3.21   64
153  ω    114.00 140.00   0.50    4.00    --   76.00  72.00-173.81   52
154  ω    116.00 142.00   0.50    4.00    --   80.00  50.00 153.53   52
155  ω     61.00  93.00   0.50    4.00    --   80.00  60.00 109.38   64
156  ω     64.00 113.00   0.50    4.00    --   80.00  50.00 153.53   98
157  ω    109.00 146.00   0.50    4.00    --   92.00  76.00-149.20   74
158  ω     67.00 102.00   0.50    4.00    --   92.00  76.00-149.20   70
159  ω     76.00 101.00   0.50    4.00    --  101.00 -42.00-120.00   50
160  ω     38.00  64.00   0.50    4.00    --  101.00 -42.00-120.00   52
161  ω    130.00 156.00   0.50    4.00    --  101.00  77.00  30.00   52
162  ω     76.00 102.00   0.50    4.00    --  101.00  77.00-120.00   52
163  ω     76.00 102.00   0.50    4.00    --  101.00  77.00  30.00   52
164  ω     76.00 108.00   0.50    4.00    --  101.00  77.00-180.00   64
165  ω    118.00 144.00   0.50    4.00    --  101.00  77.00   0.00   52
166  ω     76.00 102.00   0.50    4.00    --  101.00  77.00   0.00   52
167  ω    116.00 142.00   0.50    4.00    --  101.00  77.00 -30.00   52
168  ω     78.00 104.00   0.50    4.00    --  101.00  77.00 -30.00   52
169  ω    130.00 156.00   0.50    4.00    --  101.00  77.00 120.00   52
170  ω    127.00 154.00   0.50    4.00    --  101.00  59.00 150.00   54
171  ω     77.00 103.00   0.50    4.00    --  101.00  77.00 120.00   52
172  ω     76.00 102.00   0.50    4.00    --  101.00  77.00 150.00   52
173  ω     83.00 109.00   0.50    4.00    --  101.00  59.00 150.00   52
174  ω     76.00 112.00   0.50    4.00    --  101.00  77.00  60.00   72
175  ω     76.00 104.00   0.50    4.00    --  101.00  77.00  90.00   56
176  ω     65.00 103.00   0.50    4.00    --  101.00 -25.00 120.00   76
177  ω    131.00 156.00   0.50    4.00    --  101.00  59.00  60.00   50
178  ω     83.00 109.00   0.50    4.00    --  101.00  59.00  60.00   52
179  ω     81.00 114.00   0.50    4.00    --  101.00  68.00-180.00   66
180  ω     37.00  83.00   0.50    4.00    --  101.00 -33.00-120.00   92
181  ω     85.00 143.00   0.50    4.00    --  101.00  59.00   0.00  116
182  ω     83.00 144.00   0.50    4.00    --  101.00  59.00  30.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0027487000
_diffrn_orient_matrix_UB_12      -0.0873299000
_diffrn_orient_matrix_UB_13      -0.0759688000
_diffrn_orient_matrix_UB_21      0.0902015000
_diffrn_orient_matrix_UB_22      0.1069961000
_diffrn_orient_matrix_UB_23      -0.0264711000
_diffrn_orient_matrix_UB_31      0.0974232000
_diffrn_orient_matrix_UB_32      -0.0966364000
_diffrn_orient_matrix_UB_33      0.0391426000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3158
_reflns_number_total             3601
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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         0.303
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.055
_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)+(0.0578P)²+0.5919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1051
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C11(H11), C21(H21), C12(H12), C13(H13), C14(H14), C15(H15),
 C20(H20), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_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
F2 F 0.13556(8) 0.33831(9) 0.51957(5) 0.0337(2) Uani 1 1 d . . . . .
F3 F 0.20813(9) 0.18912(9) 0.44112(5) 0.0377(2) Uani 1 1 d . . . . .
F1 F 0.31649(8) 0.29040(10) 0.53442(5) 0.0394(2) Uani 1 1 d . . . . .
C10 C 0.48207(11) 0.45205(14) 0.28288(7) 0.0205(3) Uani 1 1 d . . . . .
C7 C 0.10899(11) 0.44648(13) 0.18457(7) 0.0232(3) Uani 1 1 d . . . . .
C9 C 0.26223(11) 0.46727(13) 0.28827(7) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.18656(11) 0.43395(13) 0.34390(7) 0.0216(3) Uani 1 1 d . . . . .
C6 C 0.03420(11) 0.41668(14) 0.24073(8) 0.0237(3) Uani 1 1 d . . . . .
H6 H -0.0449 0.4004 0.2239 0.028 Uiso 1 1 calc R . . . .
C8 C 0.22450(11) 0.47320(14) 0.20948(7) 0.0220(3) Uani 1 1 d . . . . .
H8 H 0.2772 0.4954 0.1728 0.026 Uiso 1 1 calc R . . . .
C11 C 0.48524(11) 0.31202(14) 0.25046(7) 0.0225(3) Uani 1 1 d . . . . .
H11 H 0.4235 0.2459 0.2552 0.027 Uiso 1 1 calc R . . . .
C16 C 0.23710(11) 0.59039(15) 0.46638(7) 0.0227(3) Uani 1 1 d . . . . .
C21 C 0.15989(12) 0.69495(14) 0.43377(7) 0.0243(3) Uani 1 1 d . . . . .
H21 H 0.1142 0.6737 0.3865 0.029 Uiso 1 1 calc R . . . .
C5 C 0.06943(11) 0.40944(14) 0.32053(8) 0.0233(3) Uani 1 1 d . . . . .
C1 C 0.38218(11) 0.50029(14) 0.32642(7) 0.0223(3) Uani 1 1 d . . . . .
H1 H 0.3886 0.6082 0.3353 0.027 Uiso 1 1 calc R . . . .
C12 C 0.57807(11) 0.26863(14) 0.21128(7) 0.0235(3) Uani 1 1 d . . . . .
H12 H 0.5789 0.1735 0.1892 0.028 Uiso 1 1 calc R . . . .
C13 C 0.66947(11) 0.36381(15) 0.20434(7) 0.0244(3) Uani 1 1 d . . . . .
H13 H 0.7325 0.3341 0.1774 0.029 Uiso 1 1 calc R . . . .
C3 C 0.25283(11) 0.44249(14) 0.42569(7) 0.0239(3) Uani 1 1 d . . . . .
C14 C 0.66808(12) 0.50248(15) 0.23701(8) 0.0271(3) Uani 1 1 d . . . . .
H14 H 0.7305 0.5677 0.2328 0.032 Uiso 1 1 calc R . . . .
C15 C 0.57497(12) 0.54574(14) 0.27590(8) 0.0243(3) Uani 1 1 d . . . . .
H15 H 0.5747 0.6408 0.2981 0.029 Uiso 1 1 calc R . . . .
C20 C 0.14844(12) 0.83023(15) 0.46933(8) 0.0280(3) Uani 1 1 d . . . . .
H20 H 0.0954 0.9003 0.4462 0.034 Uiso 1 1 calc R . . . .
C2 C 0.37928(12) 0.42441(17) 0.40577(8) 0.0283(3) Uani 1 1 d . . . . .
H2A H 0.4338 0.4717 0.4457 0.034 Uiso 1 1 calc R . . . .
H2B H 0.3997 0.3196 0.4024 0.034 Uiso 1 1 calc R . . . .
C17 C 0.30258(12) 0.62437(16) 0.53640(8) 0.0276(3) Uani 1 1 d . . . . .
H17 H 0.3554 0.5544 0.5599 0.033 Uiso 1 1 calc R . . . .
C23 C 0.06436(13) 0.44956(16) 0.09949(8) 0.0298(3) Uani 1 1 d . . . . .
H23A H 0.0835 0.3572 0.0751 0.045 Uiso 1 1 calc GR . . . .
H23B H 0.1001 0.5310 0.0740 0.045 Uiso 1 1 calc GR . . . .
H23C H -0.0195 0.4625 0.0942 0.045 Uiso 1 1 calc GR . . . .
C24 C -0.02000(12) 0.37655(16) 0.37524(8) 0.0309(3) Uani 1 1 d . . . . .
H24A H -0.0083 0.2772 0.3959 0.046 Uiso 1 1 calc GR . . . .
H24B H -0.0971 0.3842 0.3472 0.046 Uiso 1 1 calc GR . . . .
H24C H -0.0127 0.4469 0.4182 0.046 Uiso 1 1 calc GR . . . .
C18 C 0.29124(13) 0.75931(17) 0.57193(8) 0.0314(3) Uani 1 1 d . . . . .
H18 H 0.3364 0.7808 0.6194 0.038 Uiso 1 1 calc R . . . .
C22 C 0.22695(13) 0.31601(15) 0.47987(8) 0.0295(3) Uani 1 1 d . . . . .
C19 C 0.21441(13) 0.86274(16) 0.53849(8) 0.0312(3) Uani 1 1 d . . . . .
H19 H 0.2071 0.9550 0.5627 0.037 Uiso 1 1 calc R . . . .


_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
F2 C22 1.3416(16) . ?
F3 C22 1.3464(17) . ?
F1 C22 1.3546(17) . ?
C10 C11 1.3994(18) . ?
C10 C1 1.5166(17) . ?
C10 C15 1.3960(18) . ?
C7 C6 1.3977(18) . ?
C7 C8 1.3935(19) . ?
C7 C23 1.5110(18) . ?
C9 C4 1.4045(17) . ?
C9 C8 1.3903(18) . ?
C9 C1 1.5150(18) . ?
C4 C5 1.4025(19) . ?
C4 C3 1.5439(18) . ?
C6 H6 0.9500 . ?
C6 C5 1.4016(19) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.3928(18) . ?
C16 C21 1.3923(19) . ?
C16 C3 1.5438(18) . ?
C16 C17 1.3996(19) . ?
C21 H21 0.9500 . ?
C21 C20 1.3936(19) . ?
C5 C24 1.5092(17) . ?
C1 H1 1.0000 . ?
C1 C2 1.5420(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3907(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(2) . ?
C3 C2 1.5575(18) . ?
C3 C22 1.5377(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3924(19) . ?
C15 H15 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.387(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C18 1.390(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.388(2) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C10 C1 121.22(11) . . ?
C15 C10 C11 118.27(12) . . ?
C15 C10 C1 120.49(11) . . ?
C6 C7 C23 120.27(12) . . ?
C8 C7 C6 118.14(12) . . ?
C8 C7 C23 121.59(12) . . ?
C4 C9 C1 111.20(11) . . ?
C8 C9 C4 121.52(12) . . ?
C8 C9 C1 127.23(11) . . ?
C9 C4 C3 109.08(11) . . ?
C5 C4 C9 119.93(12) . . ?
C5 C4 C3 130.83(11) . . ?
C7 C6 H6 118.2 . . ?
C7 C6 C5 123.62(12) . . ?
C5 C6 H6 118.2 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.70(12) . . ?
C9 C8 H8 120.2 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.62(12) . . ?
C12 C11 H11 119.7 . . ?
C21 C16 C3 121.22(11) . . ?
C21 C16 C17 118.14(12) . . ?
C17 C16 C3 120.62(12) . . ?
C16 C21 H21 119.4 . . ?
C16 C21 C20 121.14(12) . . ?
C20 C21 H21 119.4 . . ?
C4 C5 C24 124.50(12) . . ?
C6 C5 C4 117.07(11) . . ?
C6 C5 C24 118.43(12) . . ?
C10 C1 H1 108.3 . . ?
C10 C1 C2 113.57(10) . . ?
C9 C1 C10 116.60(10) . . ?
C9 C1 H1 108.3 . . ?
C9 C1 C2 101.25(10) . . ?
C2 C1 H1 108.3 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.33(12) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.65(12) . . ?
C14 C13 H13 120.2 . . ?
C4 C3 C16 113.00(10) . . ?
C4 C3 C2 100.84(10) . . ?
C16 C3 C2 110.69(11) . . ?
C22 C3 C4 114.21(11) . . ?
C22 C3 C16 109.89(10) . . ?
C22 C3 C2 107.75(11) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.89(12) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.23(12) . . ?
C14 C15 H15 119.4 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 120.09(13) . . ?
C19 C20 H20 120.0 . . ?
C1 C2 C3 104.90(10) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.76(13) . . ?
C18 C17 H17 119.6 . . ?
C7 C23 H23A 109.5 . . ?
C7 C23 H23B 109.5 . . ?
C7 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 C24 H24A 109.5 . . ?
C5 C24 H24B 109.5 . . ?
C5 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.43(13) . . ?
C19 C18 H18 119.8 . . ?
F2 C22 F3 106.77(12) . . ?
F2 C22 F1 105.40(10) . . ?
F2 C22 C3 114.46(11) . . ?
F3 C22 F1 105.84(11) . . ?
F3 C22 C3 112.08(11) . . ?
F1 C22 C3 111.67(12) . . ?
C20 C19 C18 119.43(13) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?

_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 3.923
_oxdiff_exptl_absorpt_empirical_full_min 0.738
####################################################################### 
# 
# 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_7072-9949_emt105
_database_code_depnum_ccdc_archive 'CCDC 1875117'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 Br F3'
_chemical_formula_sum            'C22 H16 Br F3'
_chemical_formula_weight         417.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 F3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.02917(20)
_cell_length_b                   9.25385(19)
_cell_length_c                   11.1048(2)
_cell_angle_alpha                87.5911(16)
_cell_angle_beta                 80.5904(18)
_cell_angle_gamma                78.3143(18)
_cell_volume                     896.36(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9589
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      71.4980
_cell_measurement_theta_min      3.9720
_shelx_estimated_absorpt_T_max   0.495
_shelx_estimated_absorpt_T_min   0.280
_exptl_absorpt_coefficient_mu    3.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             420
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16363
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.987
_diffrn_reflns_theta_min         4.035
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -59.00   0.50    0.20    --  -41.35 -13.00-151.00   98
  2  ω    -24.00   7.00   0.50    0.20    --   41.35 -13.00-151.00   62
  3  ω     21.00  55.00   0.50    0.20    --   41.35 -13.00-151.00   68
  4  ω     68.00 113.00   0.50    0.20    --   41.35  13.00  20.00   90
  5  ω     45.00  91.00   0.50    0.20    --  101.00 -13.00-151.00   92
  6  ω     94.00 121.00   0.50    0.20    --  101.00  13.00  20.00   54
  7  ω     -7.00  31.00   0.50    0.20    --  -41.35  13.00  20.00   76
  8  ω    -53.00 -16.00   0.50    0.20    --  -41.35  13.00  20.00   74
  9  ω    -67.00 -19.00   0.50    0.20    --  -41.35  77.00  30.00   96
 10  ω     -3.00  22.00   0.50    0.20    --  -41.35  77.00  30.00   50
 11  ω     13.00  94.00   0.50    0.20    --   41.35-138.00-180.00  162
 12  ω     -8.00  27.00   0.50    0.20    --   41.35 -65.00-150.00   70
 13  ω     24.00  49.00   0.50    0.20    --   41.35 -32.00 120.00   50
 14  ω     46.00  72.00   0.50    0.20    --   41.35  32.00 -60.00   52
 15  ω     79.00 104.00   0.50    0.20    --   41.35  43.00 120.00   50
 16  ω     34.00  62.00   0.50    0.20    --   41.35 -65.00-150.00   56
 17  ω     74.00  99.00   0.50    0.20    --   41.35  32.00 120.00   50
 18  ω    -11.00  18.00   0.50    0.20    --   41.35 -32.00 120.00   58
 19  ω     32.00  90.00   0.50    0.20    --   41.35-138.00  90.00  116
 20  ω    -14.00  39.00   0.50    0.20    --   41.35 -32.00 -30.00  106
 21  ω     23.00  66.00   0.50    0.20    --   41.35-138.00-120.00   86
 22  ω     28.00  69.00   0.50    0.20    --   41.35  43.00 120.00   82
 23  ω     33.00  58.00   0.50    0.20    --   41.35 -54.00-180.00   50
 24  ω    -15.00  13.00   0.50    0.20    --   41.35 -54.00-180.00   56
 25  ω     76.00 123.00   0.50    0.20    --  101.00  77.00-120.00   94
 26  ω     44.00 117.00   0.50    0.20    --  101.00 -77.00  30.00  146
 27  ω     34.00 108.00   0.50    0.20    --  101.00 -25.00  60.00  148
 28  ω     86.00 111.00   0.50    0.20    --  101.00-111.00  30.00   50
 29  ω     36.00  62.00   0.50    0.20    --  101.00-111.00  30.00   52
 30  ω     42.00  98.00   0.50    0.20    --  101.00 -68.00-180.00  112
 31  ω     41.00 110.00   0.50    0.20    --  101.00 -33.00 120.00  138
 32  ω     39.00 123.00   0.50    0.20    --  101.00 -68.00 -90.00  168
 33  ω     39.00  65.00   0.50    0.20    --  101.00-133.00 150.00   52
 34  ω     97.00 154.00   0.50    0.20    --  101.00  59.00 120.00  114
 35  ω     74.00 105.00   0.50    0.20    --  101.00-111.00-120.00   62
 36  ω     81.00 131.00   0.50    0.20    --  101.00  93.00 -30.00  100
 37  ω     77.00 105.00   0.50    0.20    --  101.00 -42.00-120.00   56
 38  ω     88.00 157.00   0.50    0.20    --  101.00  42.00  30.00  138
 39  ω     51.00 104.00   0.50    0.20    --  101.00-111.00-180.00  106
 40  ω     45.00 110.00   0.50    0.20    --  101.00-111.00 -60.00  130
 41  ω     39.00  96.00   0.50    0.20    --  101.00 -68.00 120.00  114
 42  ω     94.00 143.00   0.50    0.20    --  101.00  33.00  90.00   98
 43  ω     83.00 129.00   0.50    0.20    --  101.00 -93.00 -60.00   92
 44  ω     99.00 127.00   0.50    0.20    --  101.00  93.00  30.00   56
 45  ω     36.00 105.00   0.50    0.20    --  101.00 -33.00-150.00  138
 46  ω     71.00 117.00   0.50    0.20    --  101.00 -50.00   0.00   92
 47  ω     39.00  73.00   0.50    0.20    --  101.00-133.00 -90.00   68
 48  ω    100.00 125.00   0.50    0.20    --  101.00  33.00   0.00   50
 49  ω    111.00 154.00   0.50    0.20    --  101.00  17.00 -90.00   86
 50  ω     83.00 137.00   0.50    0.20    --  101.00  68.00-180.00  108
 51  ω     48.00 105.00   0.50    0.20    --  101.00 -33.00 -30.00  114
 52  ω     64.00  89.00   0.50    0.20    --  101.00-111.00 150.00   50
 53  ω     95.00 124.00   0.50    0.20    --  101.00-133.00 150.00   58
 54  ω     16.00  42.00   0.50    0.20    --   41.35  77.00-150.00   52
 55  ω    -35.00 -10.00   0.50    0.20    --    8.00 116.00  52.26   50
 56  ω    -35.00 -10.00   0.50    0.20    --   16.00 129.00-112.05   50
 57  ω     -3.00  22.00   0.50    0.20    --   28.00  94.00-152.05   50
 58  ω     -3.00  22.00   0.50    0.20    --   28.00  96.00   7.76   50
 59  ω     -4.00  21.00   0.50    0.20    --   28.00  97.00 -49.33   50
 60  ω     -4.00  21.00   0.50    0.20    --   28.00  97.00 120.04   50
 61  ω      3.00  28.00   0.50    0.20    --   32.00  90.00-107.65   50
 62  ω      3.00  28.00   0.50    0.20    --   32.00  90.00  -7.52   50
 63  ω     15.00  40.00   0.50    0.20    --   40.00  81.00 102.37   50
 64  ω     14.00  39.00   0.50    0.20    --   40.00  82.00 155.86   50
 65  ω     19.00  44.00   0.50    0.20    --   44.00  78.00 -92.22   50
 66  ω     19.00  44.00   0.50    0.20    --   44.00  80.00 -71.15   50
 67  ω     19.00  44.00   0.50    0.20    --   44.00  79.00  44.91   50
 68  ω     18.00  43.00   0.50    0.20    --   44.00  82.00-142.93   50
 69  ω     19.00  44.00   0.50    0.20    --   44.00  81.00  61.67   50
 70  ω     18.00  43.00   0.50    0.20    --   44.00  82.00   7.64   50
 71  ω     92.00 117.00   0.50    0.20    --   52.00  77.00  55.07   50
 72  ω     32.00  78.00   0.50    0.20    --   52.00  77.00  55.07   92
 73  ω     28.00  54.00   0.50    0.20    --   52.00  76.00 159.26   52
 74  ω     28.00  53.00   0.50    0.20    --   52.00  77.00 119.76   50
 75  ω     31.00  78.00   0.50    0.20    --   56.00  77.00  25.29   94
 76  ω     79.00 105.00   0.50    0.20    --   56.00  73.00 -64.60   52
 77  ω     32.00  58.00   0.50    0.20    --   56.00  76.00 -39.28   52
 78  ω     92.00 118.00   0.50    0.20    --   56.00  76.00-114.64   52
 79  ω     35.00  61.00   0.50    0.20    --   56.00  76.00-114.64   52
 80  ω     31.00  72.00   0.50    0.20    --   56.00  76.00  91.66   82
 81  ω     34.00  60.00   0.50    0.20    --   56.00  75.00-160.17   52
 82  ω     34.00  65.00   0.50    0.20    --   56.00  73.00 -64.60   62
 83  ω     41.00  67.00   0.50    0.20    --   60.00  74.00-140.97   52
 84  ω    102.00 127.00   0.50    0.20    --   64.00  55.00 145.77   50
 85  ω     47.00  73.00   0.50    0.20    --   64.00  55.00 145.77   52
 86  ω     40.00  76.00   0.50    0.20    --   64.00  75.00 -17.86   72
 87  ω     45.00  87.00   0.50    0.20    --   64.00  68.00-179.44   84
 88  ω     57.00 110.00   0.50    0.20    --   72.00  53.00  32.21  106
 89  ω     47.00  76.00   0.50    0.20    --   72.00  77.00-163.95   58
 90  ω     59.00  85.00   0.50    0.20    --   76.00  62.00 -43.14   52
 91  ω     65.00  91.00   0.50    0.20    --   84.00  60.00 145.59   52
 92  ω    101.00 126.00   0.50    0.20    --   84.00  77.00-129.67   50
 93  ω     59.00  85.00   0.50    0.20    --   84.00  77.00-129.67   52
 94  ω     85.00 114.00   0.50    0.20    --  101.00  59.00  90.00   58
 95  ω     85.00 134.00   0.50    0.20    --  101.00  59.00 -90.00   98
 96  ω     81.00 107.00   0.50    0.20    --  101.00  68.00  30.00   52
 97  ω    121.00 154.00   0.50    0.20    --  101.00  77.00 120.00   66
 98  ω     78.00 114.00   0.50    0.20    --  101.00  77.00 120.00   72
 99  ω    107.00 133.00   0.50    0.20    --  101.00  77.00-180.00   52
100  ω    109.00 135.00   0.50    0.20    --  101.00  77.00 150.00   52
101  ω     76.00 102.00   0.50    0.20    --  101.00  77.00-180.00   52
102  ω     79.00 105.00   0.50    0.20    --  101.00  77.00 150.00   52
103  ω    120.00 147.00   0.50    0.20    --  101.00  59.00   0.00   54
104  ω     85.00 111.00   0.50    0.20    --  101.00  59.00   0.00   52
105  ω     80.00 154.00   0.50    0.20    --  101.00  68.00 -90.00  148
106  ω     85.00 136.00   0.50    0.20    --  101.00  59.00-150.00  102
107  ω     77.00 124.00   0.50    0.20    --  101.00  77.00 -60.00   94
108  ω    129.00 155.00   0.50    0.20    --  101.00  77.00  30.00   52
109  ω     85.00 111.00   0.50    0.20    --  101.00 -59.00 150.00   52
110  ω     40.00  66.00   0.50    0.20    --  101.00 -59.00 150.00   52
111  ω     77.00 102.00   0.50    0.20    --  101.00  77.00  60.00   50
112  ω     76.00 108.00   0.50    0.20    --  101.00  77.00  30.00   64
113  ω     80.00 145.00   0.50    0.20    --  101.00  68.00 150.00  130
114  ω     66.00 103.00   0.50    0.20    --  101.00 -17.00 -60.00   74
115  ω    121.00 147.00   0.50    0.20    --  101.00  59.00 -60.00   52
116  ω     86.00 117.00   0.50    0.20    --  101.00  59.00 -60.00   62
117  ω     32.00  63.00   0.50    0.20    --  101.00 -17.00 -60.00   62
118  ω    122.00 148.00   0.50    0.20    --  101.00  77.00 -30.00   52
119  ω     76.00 102.00   0.50    0.20    --  101.00  77.00 -90.00   52
120  ω     76.00 102.00   0.50    0.20    --  101.00  77.00 -30.00   52
121  ω     76.00 119.00   0.50    0.20    --  101.00  77.00  90.00   86
122  ω    132.00 157.00   0.50    0.20    --  101.00  68.00  60.00   50
123  ω     80.00 106.00   0.50    0.20    --  101.00  68.00  60.00   52
124  ω     76.00 102.00   0.50    0.20    --  101.00  77.00   0.00   52
125  ω     85.00 110.00   0.50    0.20    --  101.00 -33.00 -30.00   50
126  ω     41.00  67.00   0.50    0.20    --  101.00 -33.00 -30.00   52
127  ω     78.00 150.00   0.50    0.20    --  101.00  77.00-150.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0313728000
_diffrn_orient_matrix_UB_12      0.1579702000
_diffrn_orient_matrix_UB_13      -0.0096572000
_diffrn_orient_matrix_UB_21      -0.1736482000
_diffrn_orient_matrix_UB_22      0.0628360000
_diffrn_orient_matrix_UB_23      0.0209902000
_diffrn_orient_matrix_UB_31      0.0001241000
_diffrn_orient_matrix_UB_32      -0.0001013000
_diffrn_orient_matrix_UB_33      0.1387165000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3179
_reflns_number_total             3388
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0247
_refine_ls_restrained_S_all      1.058
_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)+(0.0279P)²+0.4765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0615
_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:
 C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C17(H17), C19(H19), C21(H21), C26(H26), C30(H30), C32(H32),
 C34(H34), C35(H35), C38(H38), C39(H39), C42(H42)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.13303(2) 1.34052(2) 0.95171(2) 0.02498(7) Uani 1 1 d . . . . .
F2 F 0.31475(12) 0.62344(11) 0.81841(9) 0.0248(2) Uani 1 1 d . . . . .
F3 F 0.51616(11) 0.67441(12) 0.70522(11) 0.0279(2) Uani 1 1 d . . . . .
F6 F 0.39861(12) 0.51622(11) 0.64457(10) 0.0286(3) Uani 1 1 d . . . . .
C8 C 0.17687(19) 1.16673(18) 0.85584(16) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.27671(18) 0.77017(18) 0.63907(15) 0.0159(3) Uani 1 1 d . . . . .
C3 C 0.10151(18) 0.77777(17) 0.49731(16) 0.0155(3) Uani 1 1 d . . . . .
C5 C 0.35701(18) 0.79584(19) 0.50732(16) 0.0176(3) Uani 1 1 d . . . . .
H5A H 0.4264 0.8661 0.5071 0.021 Uiso 1 1 calc R . . . .
H5B H 0.4169 0.7019 0.4709 0.021 Uiso 1 1 calc R . . . .
C7 C 0.24151(18) 0.91062(17) 0.71733(15) 0.0153(3) Uani 1 1 d . . . . .
C9 C 0.0315(2) 0.64958(18) 0.68660(17) 0.0194(4) Uani 1 1 d . . . . .
H9 H 0.0518 0.6136 0.7648 0.023 Uiso 1 1 calc R . . . .
C11 C 0.13093(18) 0.72559(17) 0.61261(16) 0.0158(3) Uani 1 1 d . . . . .
C14 C 0.31914(19) 1.12834(19) 0.78275(16) 0.0197(4) Uani 1 1 d . . . . .
H14 H 0.3936 1.1882 0.7796 0.024 Uiso 1 1 calc R . . . .
C16 C 0.26910(18) 0.84932(18) 0.29971(16) 0.0171(3) Uani 1 1 d . . . . .
C17 C 0.06765(19) 1.08034(18) 0.86216(16) 0.0182(3) Uani 1 1 d . . . . .
H17 H -0.0288 1.1080 0.9129 0.022 Uiso 1 1 calc R . . . .
C19 C -0.02777(19) 0.75446(18) 0.45371(17) 0.0192(4) Uani 1 1 d . . . . .
H19 H -0.0472 0.7889 0.3749 0.023 Uiso 1 1 calc R . . . .
C21 C -0.0987(2) 0.62752(19) 0.64305(17) 0.0219(4) Uani 1 1 d . . . . .
H21 H -0.1681 0.5764 0.6924 0.026 Uiso 1 1 calc R . . . .
C23 C 0.3756(2) 0.64626(19) 0.70187(17) 0.0206(4) Uani 1 1 d . . . . .
C26 C -0.12813(19) 0.67950(19) 0.52803(18) 0.0221(4) Uani 1 1 d . . . . .
H26 H -0.2174 0.6637 0.4999 0.027 Uiso 1 1 calc R . . . .
C27 C 0.22410(18) 0.86031(18) 0.43682(15) 0.0160(3) Uani 1 1 d . . . . .
H27 H 0.1887 0.9670 0.4580 0.019 Uiso 1 1 calc R . . . .
C30 C 0.34985(19) 1.00008(19) 0.71431(16) 0.0188(4) Uani 1 1 d . . . . .
H30 H 0.4468 0.9726 0.6643 0.023 Uiso 1 1 calc R . . . .
C32 C 0.28227(18) 0.97594(19) 0.22895(17) 0.0192(4) Uani 1 1 d . . . . .
H32 H 0.2584 1.0697 0.2670 0.023 Uiso 1 1 calc R . . . .
C34 C 0.3300(2) 0.9663(2) 0.10323(17) 0.0230(4) Uani 1 1 d . . . . .
H34 H 0.3394 1.0532 0.0564 0.028 Uiso 1 1 calc R . . . .
C35 C 0.10082(18) 0.95210(18) 0.79314(15) 0.0163(3) Uani 1 1 d . . . . .
H35 H 0.0264 0.8919 0.7978 0.020 Uiso 1 1 calc R . . . .
C38 C 0.30403(19) 0.71283(19) 0.24131(17) 0.0203(4) Uani 1 1 d . . . . .
H38 H 0.2959 0.6256 0.2880 0.024 Uiso 1 1 calc R . . . .
C39 C 0.3639(2) 0.8305(2) 0.04620(17) 0.0252(4) Uani 1 1 d . . . . .
H39 H 0.3959 0.8241 -0.0396 0.030 Uiso 1 1 calc R . . . .
C42 C 0.3505(2) 0.7035(2) 0.11555(18) 0.0246(4) Uani 1 1 d . . . . .
H42 H 0.3732 0.6102 0.0769 0.029 Uiso 1 1 calc R . . . .


_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 C8 1.9038(17) . ?
F2 C23 1.346(2) . ?
F3 C23 1.353(2) . ?
F6 C23 1.348(2) . ?
C8 C14 1.391(2) . ?
C8 C17 1.381(2) . ?
C2 C5 1.554(2) . ?
C2 C7 1.544(2) . ?
C2 C11 1.532(2) . ?
C2 C23 1.523(2) . ?
C3 C11 1.396(2) . ?
C3 C19 1.393(2) . ?
C3 C27 1.522(2) . ?
C5 C27 1.545(2) . ?
C7 C30 1.399(2) . ?
C7 C35 1.396(2) . ?
C9 C11 1.394(2) . ?
C9 C21 1.396(2) . ?
C14 C30 1.392(2) . ?
C16 C27 1.513(2) . ?
C16 C32 1.397(2) . ?
C16 C38 1.399(2) . ?
C17 C35 1.394(2) . ?
C19 C26 1.395(2) . ?
C21 C26 1.393(3) . ?
C32 C34 1.393(3) . ?
C34 C39 1.386(3) . ?
C38 C42 1.392(3) . ?
C39 C42 1.393(3) . ?

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
C14 C8 Br1 119.20(13) . . ?
C17 C8 Br1 119.25(13) . . ?
C17 C8 C14 121.54(16) . . ?
C7 C2 C5 112.28(13) . . ?
C11 C2 C5 100.75(13) . . ?
C11 C2 C7 112.27(13) . . ?
C23 C2 C5 110.37(13) . . ?
C23 C2 C7 109.18(14) . . ?
C23 C2 C11 111.81(14) . . ?
C11 C3 C27 110.51(14) . . ?
C19 C3 C11 120.62(15) . . ?
C19 C3 C27 128.85(16) . . ?
C27 C5 C2 104.39(13) . . ?
C30 C7 C2 120.90(15) . . ?
C35 C7 C2 121.02(14) . . ?
C35 C7 C30 118.08(16) . . ?
C11 C9 C21 118.45(17) . . ?
C3 C11 C2 109.80(14) . . ?
C9 C11 C2 129.37(16) . . ?
C9 C11 C3 120.79(16) . . ?
C8 C14 C30 118.43(16) . . ?
C32 C16 C27 120.29(15) . . ?
C32 C16 C38 118.47(16) . . ?
C38 C16 C27 121.19(15) . . ?
C8 C17 C35 119.13(16) . . ?
C3 C19 C26 118.68(17) . . ?
C26 C21 C9 120.81(16) . . ?
F2 C23 F3 106.20(14) . . ?
F2 C23 F6 106.57(14) . . ?
F2 C23 C2 113.00(14) . . ?
F3 C23 C2 111.90(14) . . ?
F6 C23 F3 106.29(14) . . ?
F6 C23 C2 112.39(14) . . ?
C21 C26 C19 120.65(16) . . ?
C3 C27 C5 101.04(13) . . ?
C16 C27 C3 117.67(14) . . ?
C16 C27 C5 113.44(13) . . ?
C14 C30 C7 121.66(16) . . ?
C34 C32 C16 120.76(17) . . ?
C39 C34 C32 120.30(17) . . ?
C17 C35 C7 121.14(15) . . ?
C42 C38 C16 120.72(16) . . ?
C34 C39 C42 119.54(17) . . ?
C38 C42 C39 120.21(17) . . ?

_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 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.858
####################################################################### 
# 
# 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_7072-9926_emt073
_database_code_depnum_ccdc_archive 'CCDC 1875115'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 Cl2 F3 O2'
_chemical_formula_sum            'C24 H19 Cl2 F3 O2'
_chemical_formula_weight         467.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.2224(5)
_cell_length_b                   10.2968(5)
_cell_length_c                   11.9735(5)
_cell_angle_alpha                74.791(4)
_cell_angle_beta                 80.463(4)
_cell_angle_gamma                72.449(5)
_cell_volume                     1041.48(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7152
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.5640
_cell_measurement_theta_min      3.7710
_shelx_estimated_absorpt_T_max   0.719
_shelx_estimated_absorpt_T_min   0.417
_exptl_absorpt_coefficient_mu    3.217
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.983
_diffrn_reflns_theta_min         3.843
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_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   -106.00 -36.00   0.50    0.50    --  -41.35 -31.00  22.00  140
  2  ω    -27.00   0.00   0.50    0.50    --  -41.35  31.00-177.00   54
  3  ω     -6.00  49.00   0.50    0.50    --   41.35 -31.00  22.00  110
  4  ω     37.00 103.00   0.50    0.50    --   41.35  31.00-177.00  132
  5  ω     94.00 148.00   0.50    2.00    --  101.00  31.00-177.00  108
  6  ω     35.00 109.00   0.50    2.00    --  101.00 -31.00  22.00  148
  7  ω    -56.00 -16.00   0.50    0.50    --  -41.35  54.00-180.00   80
  8  ω    -10.00  16.00   0.50    0.50    --  -41.35  54.00  60.00   52
  9  ω    -10.00  17.00   0.50    0.50    --  -41.35  54.00-180.00   54
 10  ω    -56.00 -16.00   0.50    0.50    --  -41.35  54.00  60.00   80
 11  ω    -39.00   6.00   0.50    0.50    --  -41.35  43.00   0.00   90
 12  ω    -11.00  15.00   0.50    0.50    --   41.35 -89.00 -30.00   52
 13  ω     49.00  92.00   0.50    0.50    --   41.35  43.00-120.00   86
 14  ω    -23.00  62.00   0.50    0.50    --   41.35 -77.00 -90.00  170
 15  ω     42.00  67.00   0.50    0.50    --   41.35  32.00 -30.00   50
 16  ω     17.00  54.00   0.50    0.50    --   41.35  77.00-120.00   74
 17  ω    -18.00  65.00   0.50    0.50    --   41.35 -77.00   0.00  166
 18  ω    -19.00   8.00   0.50    0.50    --   41.35 -65.00 120.00   54
 19  ω     22.00  48.00   0.50    0.50    --   41.35 -54.00 150.00   52
 20  ω     31.00  56.00   0.50    0.50    --   41.35 -89.00 -30.00   50
 21  ω    -12.00  13.00   0.50    0.50    --   41.35 -54.00 150.00   50
 22  ω     59.00 105.00   0.50    0.50    --   41.35  77.00-120.00   92
 23  ω     52.00  95.00   0.50    0.50    --   41.35-138.00-180.00   86
 24  ω     34.00  59.00   0.50    0.50    --   41.35 -65.00 120.00   50
 25  ω    112.00 156.00   0.50    2.00    --  101.00  42.00 150.00   88
 26  ω     47.00  90.00   0.50    2.00    --  101.00-111.00-150.00   86
 27  ω    123.00 155.00   0.50    2.00    --  101.00  25.00  60.00   64
 28  ω     40.00  85.00   0.50    2.00    --  101.00 -68.00  60.00   90
 29  ω     72.00  97.00   0.50    2.00    --  101.00-133.00  30.00   50
 30  ω     41.00  67.00   0.50    2.00    --  101.00-133.00  30.00   52
 31  ω     47.00 101.00   0.50    2.00    --  101.00 -25.00 120.00  108
 32  ω     88.00 114.00   0.50    2.00    --  101.00 -68.00  60.00   52
 33  ω     42.00 110.00   0.50    2.00    --  101.00 -25.00-150.00  136
 34  ω     85.00 149.00   0.50    2.00    --  101.00  59.00   0.00  128
 35  ω     81.00 116.00   0.50    2.00    --  101.00 -50.00 150.00   70
 36  ω     85.00 111.00   0.50    2.00    --  101.00  59.00  60.00   52
 37  ω     39.00 115.00   0.50    2.00    --  101.00-111.00  60.00  152
 38  ω     97.00 155.00   0.50    2.00    --  101.00  25.00 120.00  116
 39  ω    103.00 154.00   0.50    2.00    --  101.00  42.00  30.00  102
 40  ω     53.00 117.00   0.50    2.00    --  101.00 -50.00  60.00  128
 41  ω     82.00 116.00   0.50    2.00    --  101.00 -87.00  60.00   68
 42  ω     47.00  73.00   0.50    2.00    --  101.00 -59.00-120.00   52
 43  ω    128.00 153.00   0.50    2.00    --  101.00  68.00 -60.00   50
 44  ω     38.00 115.00   0.50    2.00    --  101.00 -50.00 -60.00  154
 45  ω     92.00 153.00   0.50    2.00    --  101.00  33.00 -90.00  122
 46  ω     65.00 105.00   0.50    2.00    --  101.00-111.00-120.00   80
 47  ω     38.00 123.00   0.50    2.00    --  101.00 -77.00-150.00  170
 48  ω     37.00  79.00   0.50    2.00    --  101.00 -87.00  60.00   84
 49  ω     77.00 114.00   0.50    2.00    --  101.00-111.00-180.00   74
 50  ω     44.00  79.00   0.50    2.00    --  101.00-133.00   0.00   70
 51  ω     91.00 116.00   0.50    2.00    --  101.00-133.00   0.00   50
 52  ω     45.00  71.00   0.50    2.00    --  101.00 -50.00 150.00   52
 53  ω     40.00 122.00   0.50    2.00    --  101.00-133.00  60.00  164
 54  ω     47.00  73.00   0.50    2.00    --  101.00-133.00-160.00   52
 55  ω    -32.00  -7.00   0.50    0.50    --    8.00 112.00  53.28   50
 56  ω    -22.00   3.00   0.50    0.50    --   16.00 108.00-115.27   50
 57  ω    -43.00 -18.00   0.50    0.50    --   24.00 153.00  26.46   50
 58  ω     -3.00  22.00   0.50    0.50    --   28.00  94.00-101.99   50
 59  ω      3.00  28.00   0.50    0.50    --   32.00  90.00-117.85   50
 60  ω      2.00  27.00   0.50    0.50    --   32.00  91.00  35.56   50
 61  ω      3.00  28.00   0.50    0.50    --   32.00  90.00 174.27   50
 62  ω      3.00  28.00   0.50    0.50    --   32.00  90.00 112.01   50
 63  ω      4.00  29.00   0.50    0.50    --   32.00  88.00 -27.59   50
 64  ω     10.00  35.00   0.50    0.50    --   36.00  83.00  81.59   50
 65  ω     10.00  35.00   0.50    0.50    --   36.00  83.00 132.27   50
 66  ω      9.00  34.00   0.50    0.50    --   36.00  85.00 -65.61   50
 67  ω     14.00  39.00   0.50    0.50    --   40.00  82.00  -6.09   50
 68  ω     46.00  72.00   0.50    0.50    --   41.35-104.00-150.00   52
 69  ω     19.00  44.00   0.50    0.50    --   44.00  81.00 138.27   50
 70  ω     19.00  44.00   0.50    0.50    --   44.00  79.00 102.47   50
 71  ω     19.00  44.00   0.50    0.50    --   44.00  80.00-171.04   50
 72  ω     18.00  43.00   0.50    0.50    --   44.00  82.00  25.66   50
 73  ω     19.00  44.00   0.50    0.50    --   44.00  80.00  55.87   50
 74  ω     19.00  44.00   0.50    0.50    --   44.00  81.00 -47.50   50
 75  ω     19.00  44.00   0.50    0.50    --   44.00  80.00-118.98   50
 76  ω     28.00  54.00   0.50    0.50    --   48.00  77.00 -97.97   52
 77  ω     27.00  53.00   0.50    0.50    --   52.00  76.00 -12.47   52
 78  ω     27.00  53.00   0.50    0.50    --   52.00  77.00 120.53   52
 79  ω     27.00  53.00   0.50    0.50    --   52.00  77.00 152.04   52
 80  ω     29.00  55.00   0.50    0.50    --   52.00  76.00-136.53   52
 81  ω     29.00  69.00   0.50    0.50    --   52.00  74.00  23.76   80
 82  ω     28.00  54.00   0.50    0.50    --   52.00  77.00-176.62   52
 83  ω     31.00  57.00   0.50    0.50    --   56.00  77.00  68.94   52
 84  ω     42.00  68.00   0.50    0.50    --   60.00  67.00-118.35   52
 85  ω     40.00  86.00   0.50    0.50    --   60.00  64.00  79.84   92
 86  ω    103.00 128.00   0.50    0.50    --   64.00  72.00 -52.70   50
 87  ω     42.00  92.00   0.50    0.50    --   64.00  72.00 -52.70  100
 88  ω     41.00  72.00   0.50    0.50    --   64.00  77.00 120.97   62
 89  ω     41.00  77.00   0.50    0.50    --   64.00  72.00 175.63   72
 90  ω     80.00 106.00   0.50    0.50    --   64.00  72.00 175.63   52
 91  ω     43.00  69.00   0.50    0.50    --   64.00  72.00-148.40   52
 92  ω     39.00  64.00   0.50    0.50    --   64.00  77.00 -93.83   50
 93  ω     43.00 116.00   0.50    0.50    --   68.00  77.00 -19.83  146
 94  ω    104.00 130.00   0.50    0.50    --   68.00  66.00  32.08   52
 95  ω     56.00  82.00   0.50    0.50    --   68.00  66.00  32.08   52
 96  ω     46.00  72.00   0.50    0.50    --   68.00  74.00  98.04   52
 97  ω     47.00  91.50   0.50    2.00    --   72.00  76.00   5.48   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0298432000
_diffrn_orient_matrix_UB_12      -0.1515860000
_diffrn_orient_matrix_UB_13      -0.0115775000
_diffrn_orient_matrix_UB_21      -0.1646617000
_diffrn_orient_matrix_UB_22      0.0012165000
_diffrn_orient_matrix_UB_23      0.0520099000
_diffrn_orient_matrix_UB_31      -0.0544758000
_diffrn_orient_matrix_UB_32      0.0544396000
_diffrn_orient_matrix_UB_33      -0.1228685000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3470
_reflns_number_total             3943
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.059
_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)+(0.0994P)²+0.6549P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1574
_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:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C18(H18), C9(H9), C6(H6), C13(H13), C22(H22), C14(H14),
 C21(H21), C15(H15)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.04782(7) 0.46209(7) 0.79600(5) 0.0336(2) Uani 1 1 d . . . . .
Cl1 Cl 0.39272(7) 0.46150(7) 0.71373(6) 0.0353(2) Uani 1 1 d . . . . .
F2 F 0.18768(16) 0.28779(16) 0.08819(12) 0.0312(3) Uani 1 1 d . . . . .
F1 F 0.36471(18) 0.39028(15) 0.01315(12) 0.0321(4) Uani 1 1 d . . . . .
F3 F 0.39045(17) 0.18110(15) -0.00502(11) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.2377(2) -0.23433(18) 0.28932(14) 0.0266(4) Uani 1 1 d . . . . .
O1 O 0.1869(2) -0.21260(18) 0.50311(14) 0.0266(4) Uani 1 1 d . . . . .
C19 C 0.2935(3) 0.3971(2) 0.6391(2) 0.0245(5) Uani 1 1 d . . . . .
C20 C 0.1409(3) 0.4010(2) 0.6737(2) 0.0251(5) Uani 1 1 d . . . . .
C17 C 0.2933(3) 0.2874(2) 0.4842(2) 0.0233(5) Uani 1 1 d . . . . .
C5 C 0.3596(3) 0.0838(2) 0.2584(2) 0.0221(5) Uani 1 1 d . . . . .
C16 C 0.6827(3) 0.0307(3) 0.1795(2) 0.0277(5) Uani 1 1 d . . . . .
H16 H 0.6352 -0.0430 0.2097 0.033 Uiso 1 1 calc R . . . .
C3 C 0.3804(3) 0.2192(2) 0.3861(2) 0.0242(5) Uani 1 1 d . . . . .
H3 H 0.4914 0.1884 0.3986 0.029 Uiso 1 1 calc R . . . .
C12 C 0.6665(3) 0.2753(3) 0.11075(19) 0.0244(5) Uani 1 1 d . . . . .
H12 H 0.6073 0.3700 0.0933 0.029 Uiso 1 1 calc R . . . .
C18 C 0.3696(3) 0.3403(2) 0.5458(2) 0.0237(5) Uani 1 1 d . . . . .
H18 H 0.4741 0.3372 0.5237 0.028 Uiso 1 1 calc R . . . .
C4 C 0.3363(3) 0.0939(2) 0.3733(2) 0.0229(5) Uani 1 1 d . . . . .
C9 C 0.2803(3) -0.0048(2) 0.4594(2) 0.0234(5) Uani 1 1 d . . . . .
H9 H 0.2656 0.0016 0.5384 0.028 Uiso 1 1 calc R . . . .
C8 C 0.2465(3) -0.1126(2) 0.42803(19) 0.0221(5) Uani 1 1 d . . . . .
C11 C 0.5930(3) 0.1684(2) 0.15618(19) 0.0226(5) Uani 1 1 d . . . . .
C6 C 0.3313(3) -0.0260(2) 0.22573(19) 0.0231(5) Uani 1 1 d . . . . .
H6 H 0.3510 -0.0338 0.1470 0.028 Uiso 1 1 calc R . . . .
C2 C 0.3631(3) 0.3120(2) 0.2632(2) 0.0240(5) Uani 1 1 d . . . . .
H2A H 0.4279 0.3774 0.2457 0.029 Uiso 1 1 calc R . . . .
H2B H 0.2555 0.3666 0.2540 0.029 Uiso 1 1 calc R . . . .
C13 C 0.8253(3) 0.2434(3) 0.0911(2) 0.0274(5) Uani 1 1 d . . . . .
H13 H 0.8738 0.3165 0.0611 0.033 Uiso 1 1 calc R . . . .
C24 C 0.2617(3) -0.2487(3) 0.1715(2) 0.0266(5) Uani 1 1 d . . . . .
H24A H 0.2029 -0.1633 0.1223 0.040 Uiso 1 1 calc GR . . . .
H24B H 0.2280 -0.3286 0.1669 0.040 Uiso 1 1 calc GR . . . .
H24C H 0.3705 -0.2640 0.1447 0.040 Uiso 1 1 calc GR . . . .
C1 C 0.4171(3) 0.2064(2) 0.18283(19) 0.0213(5) Uani 1 1 d . . . . .
C22 C 0.1382(3) 0.2976(3) 0.5164(2) 0.0259(5) Uani 1 1 d . . . . .
H22 H 0.0837 0.2660 0.4730 0.031 Uiso 1 1 calc R . . . .
C7 C 0.2738(3) -0.1241(2) 0.3106(2) 0.0217(5) Uani 1 1 d . . . . .
C14 C 0.9129(3) 0.1054(3) 0.1154(2) 0.0301(5) Uani 1 1 d . . . . .
H14 H 1.0211 0.0839 0.1021 0.036 Uiso 1 1 calc R . . . .
C21 C 0.0626(3) 0.3529(3) 0.6106(2) 0.0270(5) Uani 1 1 d . . . . .
H21 H -0.0426 0.3580 0.6320 0.032 Uiso 1 1 calc R . . . .
C23 C 0.1414(3) -0.1934(3) 0.6194(2) 0.0272(5) Uani 1 1 d . . . . .
H23A H 0.0667 -0.1023 0.6176 0.041 Uiso 1 1 calc GR . . . .
H23B H 0.2311 -0.1972 0.6554 0.041 Uiso 1 1 calc GR . . . .
H23C H 0.0954 -0.2676 0.6648 0.041 Uiso 1 1 calc GR . . . .
C10 C 0.3401(3) 0.2657(3) 0.0701(2) 0.0251(5) Uani 1 1 d . . . . .
C15 C 0.8419(3) -0.0008(3) 0.1592(2) 0.0329(6) Uani 1 1 d . . . . .
H15 H 0.9016 -0.0954 0.1755 0.039 Uiso 1 1 calc R . . . .


_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
Cl2 C20 1.738(2) . ?
Cl1 C19 1.738(2) . ?
F2 C10 1.344(3) . ?
F1 C10 1.352(3) . ?
F3 C10 1.346(3) . ?
O2 C24 1.431(3) . ?
O2 C7 1.368(3) . ?
O1 C8 1.365(3) . ?
O1 C23 1.434(3) . ?
C19 C20 1.391(3) . ?
C19 C18 1.385(3) . ?
C20 C21 1.389(4) . ?
C17 C3 1.517(3) . ?
C17 C18 1.396(3) . ?
C17 C22 1.399(3) . ?
C5 C4 1.382(3) . ?
C5 C6 1.394(3) . ?
C5 C1 1.529(3) . ?
C16 C11 1.391(4) . ?
C16 C15 1.399(4) . ?
C3 C4 1.515(3) . ?
C3 C2 1.534(3) . ?
C12 C11 1.407(3) . ?
C12 C13 1.395(3) . ?
C4 C9 1.398(3) . ?
C9 C8 1.392(3) . ?
C8 C7 1.417(3) . ?
C11 C1 1.549(3) . ?
C6 C7 1.393(3) . ?
C2 C1 1.556(3) . ?
C13 C14 1.388(4) . ?
C1 C10 1.524(3) . ?
C22 C21 1.386(3) . ?
C14 C15 1.384(4) . ?

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
C7 O2 C24 117.07(17) . . ?
C8 O1 C23 115.99(18) . . ?
C20 C19 Cl1 120.47(18) . . ?
C18 C19 Cl1 118.88(18) . . ?
C18 C19 C20 120.6(2) . . ?
C19 C20 Cl2 121.01(19) . . ?
C21 C20 Cl2 119.48(18) . . ?
C21 C20 C19 119.5(2) . . ?
C18 C17 C3 119.6(2) . . ?
C18 C17 C22 118.5(2) . . ?
C22 C17 C3 121.9(2) . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 C1 109.60(19) . . ?
C6 C5 C1 129.2(2) . . ?
C11 C16 C15 120.9(2) . . ?
C17 C3 C2 115.6(2) . . ?
C4 C3 C17 116.31(19) . . ?
C4 C3 C2 100.79(18) . . ?
C13 C12 C11 120.6(2) . . ?
C19 C18 C17 120.3(2) . . ?
C5 C4 C3 110.8(2) . . ?
C5 C4 C9 120.5(2) . . ?
C9 C4 C3 128.7(2) . . ?
C8 C9 C4 119.2(2) . . ?
O1 C8 C9 124.8(2) . . ?
O1 C8 C7 115.2(2) . . ?
C9 C8 C7 120.0(2) . . ?
C16 C11 C12 118.3(2) . . ?
C16 C11 C1 121.9(2) . . ?
C12 C11 C1 119.8(2) . . ?
C7 C6 C5 118.8(2) . . ?
C3 C2 C1 103.94(18) . . ?
C14 C13 C12 120.2(2) . . ?
C5 C1 C11 113.02(19) . . ?
C5 C1 C2 100.72(17) . . ?
C11 C1 C2 110.75(18) . . ?
C10 C1 C5 111.11(18) . . ?
C10 C1 C11 110.22(18) . . ?
C10 C1 C2 110.71(19) . . ?
C21 C22 C17 121.1(2) . . ?
O2 C7 C8 115.28(19) . . ?
O2 C7 C6 124.5(2) . . ?
C6 C7 C8 120.2(2) . . ?
C15 C14 C13 119.7(2) . . ?
C22 C21 C20 119.8(2) . . ?
F2 C10 F1 106.10(19) . . ?
F2 C10 F3 106.81(18) . . ?
F2 C10 C1 112.37(19) . . ?
F1 C10 C1 112.08(19) . . ?
F3 C10 F1 106.34(18) . . ?
F3 C10 C1 112.67(19) . . ?
C14 C15 C16 120.3(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 2.623
_oxdiff_exptl_absorpt_empirical_full_min 0.662
####################################################################### 
# 
# 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_7072-9921_emt072
_database_code_depnum_ccdc_archive 'CCDC 1875116'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 Cl2 F3'
_chemical_formula_sum            'C22 H15 Cl2 F3'
_chemical_formula_weight         407.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'F3 C20'
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'
Cl Cl 0.1484 0.1585 '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           15
_space_group_name_H-M_alt        'I 1 2/c 1'
_space_group_name_Hall           '-I 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   21.8668(5)
_cell_length_b                   10.36934(16)
_cell_length_c                   18.0539(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.947(3)
_cell_angle_gamma                90
_cell_volume                     3741.24(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9556
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.9260
_cell_measurement_theta_min      2.9920
_shelx_estimated_absorpt_T_max   0.882
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.34
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23048
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.738
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -97.00  -70.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.2058  178.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   46.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.2058   57.0000 -180.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   48.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.2058   19.0000  -60.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00  -19.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.2058   19.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega    8.00   38.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1433   57.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  6 omega  -37.00   -8.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.2058  -77.0000  -90.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega  -83.00  -53.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.2058 -178.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega    4.00   91.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1433   57.0000   60.0000 87

#__ type_ start__ end____ width___ exp.time_
  9 omega  -12.00   53.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1433   19.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 10 omega  -52.00  -26.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.2058   19.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  -12.00   13.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1433   90.0000   -7.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   16.00   65.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1433  -99.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
 13 omega   20.00   66.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       24.1433  -99.0000 -120.0000 46
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0139782000
_diffrn_orient_matrix_UB_12      -0.0131643000
_diffrn_orient_matrix_UB_13      -0.0422022000
_diffrn_orient_matrix_UB_21      0.0292234000
_diffrn_orient_matrix_UB_22      0.0246672000
_diffrn_orient_matrix_UB_23      -0.0028282000
_diffrn_orient_matrix_UB_31      0.0144935000
_diffrn_orient_matrix_UB_32      -0.0624177000
_diffrn_orient_matrix_UB_33      0.0077558000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3740
_reflns_number_total             4297
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.030
_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)+(0.0441P)²+8.3240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1068
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C22(H22), C9(H9), C7(H7), C12(H12), C14(H14), C18(H18), C16(H16),
 C8(H8), C15(H15), C19(H19), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.55104(3) 0.28703(5) 0.96739(3) 0.03079(14) Uani 1 1 d . . . . .
Cl1 Cl 0.52370(3) 0.58076(6) 0.91467(3) 0.03763(16) Uani 1 1 d . . . . .
F1 F 0.63168(6) -0.22839(11) 0.68220(8) 0.0317(3) Uani 1 1 d . . . . .
F2 F 0.53863(6) -0.12532(13) 0.62328(8) 0.0340(3) Uani 1 1 d . . . . .
F3 F 0.58439(7) -0.14181(12) 0.75376(8) 0.0351(3) Uani 1 1 d . . . . .
C5 C 0.70352(8) 0.14000(17) 0.80102(10) 0.0163(3) Uani 1 1 d . . . . .
C10 C 0.69814(9) 0.01451(17) 0.77132(10) 0.0175(3) Uani 1 1 d . . . . .
C17 C 0.61800(9) 0.31376(17) 0.79242(10) 0.0176(3) Uani 1 1 d . . . . .
C20 C 0.56227(9) 0.47924(19) 0.87026(12) 0.0246(4) Uani 1 1 d . . . . .
C11 C 0.65165(9) 0.01120(17) 0.61664(10) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.63525(9) 0.00179(17) 0.69209(10) 0.0184(4) Uani 1 1 d . . . . .
C21 C 0.57276(9) 0.35029(19) 0.89235(11) 0.0216(4) Uani 1 1 d . . . . .
C4 C 0.64458(9) 0.22144(17) 0.74766(10) 0.0177(3) Uani 1 1 d . . . . .
H4 H 0.6575 0.2715 0.7089 0.021 Uiso 1 1 calc R . . . .
C6 C 0.75799(9) 0.17691(19) 0.87069(11) 0.0207(4) Uani 1 1 d . . . . .
H6 H 0.7616 0.2626 0.8906 0.025 Uiso 1 1 calc R . . . .
C22 C 0.60061(9) 0.26827(17) 0.85377(11) 0.0194(4) Uani 1 1 d . . . . .
H22 H 0.6079 0.1802 0.8694 0.023 Uiso 1 1 calc R . . . .
C3 C 0.59301(9) 0.11713(18) 0.70019(11) 0.0200(4) Uani 1 1 d . . . . .
H3A H 0.5628 0.1496 0.6461 0.024 Uiso 1 1 calc R . . . .
H3B H 0.5658 0.0911 0.7301 0.024 Uiso 1 1 calc R . . . .
C9 C 0.74662(10) -0.07654(19) 0.81234(11) 0.0238(4) Uani 1 1 d . . . . .
H9 H 0.7426 -0.1627 0.7931 0.029 Uiso 1 1 calc R . . . .
C7 C 0.80716(9) 0.0861(2) 0.91069(11) 0.0254(4) Uani 1 1 d . . . . .
H7 H 0.8451 0.1103 0.9579 0.030 Uiso 1 1 calc R . . . .
C12 C 0.60654(9) 0.06523(19) 0.54446(11) 0.0232(4) Uani 1 1 d . . . . .
H12 H 0.5645 0.0959 0.5411 0.028 Uiso 1 1 calc R . . . .
C14 C 0.68275(10) 0.0286(2) 0.48064(11) 0.0253(4) Uani 1 1 d . . . . .
H14 H 0.6934 0.0355 0.4348 0.030 Uiso 1 1 calc R . . . .
C1 C 0.59782(10) -0.1234(2) 0.68797(12) 0.0257(4) Uani 1 1 d . . . . .
C18 C 0.60867(9) 0.44395(18) 0.77188(11) 0.0223(4) Uani 1 1 d . . . . .
H18 H 0.6213 0.4766 0.7309 0.027 Uiso 1 1 calc R . . . .
C16 C 0.71225(9) -0.03555(19) 0.61929(11) 0.0224(4) Uani 1 1 d . . . . .
H16 H 0.7435 -0.0733 0.6678 0.027 Uiso 1 1 calc R . . . .
C8 C 0.80127(10) -0.0398(2) 0.88211(11) 0.0283(4) Uani 1 1 d . . . . .
H8 H 0.8348 -0.1013 0.9104 0.034 Uiso 1 1 calc R . . . .
C15 C 0.72762(10) -0.0277(2) 0.55156(11) 0.0265(4) Uani 1 1 d . . . . .
H15 H 0.7689 -0.0610 0.5540 0.032 Uiso 1 1 calc R . . . .
C19 C 0.58099(10) 0.52673(19) 0.81090(12) 0.0262(4) Uani 1 1 d . . . . .
H19 H 0.5750 0.6155 0.7968 0.031 Uiso 1 1 calc R . . . .
C13 C 0.62229(10) 0.0747(2) 0.47719(11) 0.0269(4) Uani 1 1 d . . . . .
H13 H 0.5913 0.1132 0.4287 0.032 Uiso 1 1 calc R . . . .


_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
Cl2 C21 1.7359(19) . ?
Cl1 C20 1.7353(18) . ?
F1 C1 1.344(2) . ?
F2 C1 1.346(2) . ?
F3 C1 1.348(2) . ?
C5 C10 1.394(2) . ?
C5 C4 1.515(2) . ?
C5 C6 1.390(3) . ?
C10 C2 1.535(2) . ?
C10 C9 1.388(2) . ?
C17 C4 1.513(2) . ?
C17 C22 1.391(2) . ?
C17 C18 1.393(3) . ?
C20 C21 1.387(3) . ?
C20 C19 1.384(3) . ?
C11 C2 1.546(2) . ?
C11 C12 1.393(3) . ?
C11 C16 1.393(2) . ?
C2 C3 1.554(2) . ?
C2 C1 1.520(3) . ?
C21 C22 1.387(2) . ?
C4 C3 1.546(3) . ?
C6 C7 1.390(3) . ?
C9 C8 1.392(3) . ?
C7 C8 1.390(3) . ?
C12 C13 1.394(3) . ?
C14 C15 1.387(3) . ?
C14 C13 1.383(3) . ?
C18 C19 1.395(3) . ?
C16 C15 1.396(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C5 C4 111.01(15) . . ?
C6 C5 C10 120.85(16) . . ?
C6 C5 C4 128.13(16) . . ?
C5 C10 C2 110.02(15) . . ?
C9 C10 C5 120.18(17) . . ?
C9 C10 C2 129.79(17) . . ?
C22 C17 C4 119.94(16) . . ?
C22 C17 C18 118.86(16) . . ?
C18 C17 C4 121.17(16) . . ?
C21 C20 Cl1 120.42(16) . . ?
C19 C20 Cl1 119.60(16) . . ?
C19 C20 C21 119.95(17) . . ?
C12 C11 C2 121.33(16) . . ?
C12 C11 C16 118.32(16) . . ?
C16 C11 C2 120.35(16) . . ?
C10 C2 C11 112.02(14) . . ?
C10 C2 C3 100.84(13) . . ?
C11 C2 C3 113.18(15) . . ?
C1 C2 C10 112.32(15) . . ?
C1 C2 C11 108.88(14) . . ?
C1 C2 C3 109.45(15) . . ?
C20 C21 Cl2 121.52(14) . . ?
C22 C21 Cl2 118.37(15) . . ?
C22 C21 C20 120.11(17) . . ?
C5 C4 C3 101.73(14) . . ?
C17 C4 C5 115.17(14) . . ?
C17 C4 C3 112.76(14) . . ?
C5 C6 C7 118.79(18) . . ?
C21 C22 C17 120.62(17) . . ?
C4 C3 C2 105.24(14) . . ?
C10 C9 C8 119.07(18) . . ?
C8 C7 C6 120.49(18) . . ?
C11 C12 C13 120.78(17) . . ?
C13 C14 C15 119.49(17) . . ?
F1 C1 F2 106.65(16) . . ?
F1 C1 F3 106.10(16) . . ?
F1 C1 C2 113.14(15) . . ?
F2 C1 F3 106.60(16) . . ?
F2 C1 C2 111.35(16) . . ?
F3 C1 C2 112.54(16) . . ?
C17 C18 C19 120.58(18) . . ?
C11 C16 C15 120.89(17) . . ?
C7 C8 C9 120.60(18) . . ?
C14 C15 C16 120.10(18) . . ?
C20 C19 C18 119.84(18) . . ?
C14 C13 C12 120.40(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_7072-9911_emt086
_database_code_depnum_ccdc_archive 'CCDC 1875118'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 F3'
_chemical_formula_sum            'C24 H21 F3'
_chemical_formula_weight         366.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.1714(3)
_cell_length_b                   36.8462(10)
_cell_length_c                   10.1929(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.732(3)
_cell_angle_gamma                90
_cell_volume                     3710.87(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12584
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.8500
_cell_measurement_theta_min      2.4500
_shelx_estimated_absorpt_T_max   0.864
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1536
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28863
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.000
_diffrn_reflns_theta_min         2.398
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_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     -9.00  33.00   0.50    0.87    --   41.35-109.00 -20.00   84
  2  ω     39.00  66.00   0.50    0.87    --   41.35-109.00 -20.00   54
  3  ω     65.00 110.00   0.50    4.00    --  101.00-109.00 -20.00   90
  4  ω     82.00 150.00   0.50    4.00    --  101.00 109.00  75.00  136
  5  ω    -77.00 -50.00   0.50    0.87    --  -41.35 -32.00-150.00   54
  6  ω    -75.00 -46.00   0.50    0.87    --  -41.35 109.00  75.00   58
  7  ω    -49.00  21.00   0.50    0.87    --  -41.35  32.00  90.00  140
  8  ω    -65.00  10.00   0.50    0.87    --  -41.35  77.00-180.00  150
  9  ω   -106.00 -79.00   0.50    0.87    --  -41.35 -32.00-150.00   54
 10  ω    -43.00 -16.00   0.50    0.87    --  -41.35 109.00  75.00   54
 11  ω    -42.00  22.00   0.50    0.87    --  -41.35  65.00 120.00  128
 12  ω     -6.00  20.00   0.50    0.87    --   41.35 -54.00 -90.00   52
 13  ω     24.00 102.00   0.50    0.87    --   41.35  54.00 -90.00  156
 14  ω     25.00  57.00   0.50    0.87    --   41.35 -54.00 -90.00   64
 15  ω      8.00  41.00   0.50    0.87    --   41.35 -65.00 -30.00   66
 16  ω     76.00 105.00   0.50    0.87    --   41.35  65.00 120.00   58
 17  ω     72.00  99.00   0.50    0.87    --   41.35  65.00-180.00   54
 18  ω     23.00  58.00   0.50    0.87    --   41.35  65.00-180.00   70
 19  ω     52.00  97.00   0.50    4.00    --  101.00 -42.00   0.00   90
 20  ω    116.00 150.00   0.50    4.00    --  101.00  33.00 -30.00   68
 21  ω     39.00  98.00   0.50    4.00    --  101.00 -87.00 -30.00  118
 22  ω     37.00 105.00   0.50    4.00    --  101.00 -33.00 -90.00  136
 23  ω     77.00 131.00   0.50    4.00    --  101.00  77.00 120.00  108
 24  ω     39.00 118.00   0.50    4.00    --  101.00 -59.00 120.00  158
 25  ω     78.00 124.00   0.50    4.00    --  101.00-133.00 120.00   92
 26  ω     40.00  67.00   0.50    4.00    --  101.00-133.00 120.00   54
 27  ω     88.00 118.00   0.50    4.00    --  101.00  17.00-120.00   60
 28  ω    109.00 143.00   0.50    4.00    --  101.00   8.00 150.00   68
 29  ω     44.00 123.00   0.50    4.00    --  101.00 -68.00   0.00  158
 30  ω     45.00  90.00   0.50    4.00    --  101.00 -68.00 -30.00   90
 31  ω     72.00  99.00   0.50    4.00    --  101.00   8.00 150.00   54
 32  ω     90.00 136.00   0.50    4.00    --  101.00  17.00  30.00   92
 33  ω     38.00  65.00   0.50    4.00    --  101.00 -77.00  30.00   54
 34  ω     92.00 118.00   0.50    4.00    --  101.00 -77.00  30.00   52
 35  ω    117.00 156.00   0.50    4.00    --  101.00  77.00  30.00   78
 36  ω    125.00 154.00   0.50    4.00    --  101.00  33.00  30.00   58
 37  ω    120.00 157.00   0.50    4.00    --  101.00  33.00-120.00   74
 38  ω     82.00 107.00   0.50    4.00    --  101.00 109.00  75.00   50
 39  ω   -104.00 -53.00   0.50    0.87    --  -41.35 -21.00 -60.00  102
 40  ω   -104.00 -34.00   0.50    0.87    --  -41.35 -77.00  30.00  140
 41  ω    -55.00  15.00   0.50    0.87    --  -41.35  43.00 -60.00  140
 42  ω     15.00  41.00   0.50    0.87    --   41.35-138.00 -30.00   52
 43  ω      4.00  51.00   0.50    0.87    --   41.35 -21.00  60.00   94
 44  ω     57.00  84.00   0.50    0.87    --   41.35  32.00 -30.00   54
 45  ω     48.00  79.00   0.50    0.87    --   41.35-138.00 -30.00   62
 46  ω    -20.00  17.00   0.50    0.87    --   41.35 -65.00-150.00   74
 47  ω     40.00  68.00   0.50    4.00    --  101.00-133.00-180.00   56
 48  ω     89.00 121.00   0.50    4.00    --  101.00  17.00-150.00   64
 49  ω     82.00 110.00   0.50    4.00    --  101.00 -25.00 -30.00   56
 50  ω    130.00 157.00   0.50    4.00    --  101.00  17.00-150.00   54
 51  ω     99.00 124.00   0.50    4.00    --  101.00  -8.00  60.00   50
 52  ω     67.00  76.50   0.50    4.00    --  101.00 -59.00-150.00   19
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0077524000
_diffrn_orient_matrix_UB_12      0.0361935000
_diffrn_orient_matrix_UB_13      0.0773307000
_diffrn_orient_matrix_UB_21      -0.0824774000
_diffrn_orient_matrix_UB_22      0.0186548000
_diffrn_orient_matrix_UB_23      -0.1286104000
_diffrn_orient_matrix_UB_31      -0.1320851000
_diffrn_orient_matrix_UB_32      -0.0095600000
_diffrn_orient_matrix_UB_33      0.0410571000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6148
_reflns_number_total             7038
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.952
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7038
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.033
_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)+(0.0846P)²+2.6462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1543
_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:
 C4B(H4B), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3B(H3BA,H3BB), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C8B(H8B), C22B(H22B), C6(H6), C16(H16), C22(H22), C9B(H9B),
 C6B(H6B), C18(H18), C18B(H18B), C7B(H7B), C21(H21), C19B(H19B), C21B(H21B),
 C8(H8), C20(H20), C7(H7), C12B(H12B), C20B(H20B), C19(H19), C16B(H16B),
 C14(H14), C14B(H14B)
2.d Idealised Me refined as rotating group:
 C23(H23D,H23E,H23F), C24(H24D,H24E,H24F), C23B(H23A,H23B,H23C), C24B(H24A,
 H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F2B F 0.45211(12) 0.34427(3) 0.18757(11) 0.0297(3) Uani 1 1 d . . . . .
F1B F 0.36154(11) 0.36230(3) 0.34738(12) 0.0306(3) Uani 1 1 d . . . . .
F3B F 0.46700(12) 0.31131(3) 0.36531(12) 0.0315(3) Uani 1 1 d . . . . .
F3 F 0.88148(14) 0.69260(4) 0.13241(13) 0.0380(3) Uani 1 1 d . . . . .
F2 F 0.96073(14) 0.70417(3) 0.34391(14) 0.0396(3) Uani 1 1 d . . . . .
F1 F 1.03827(12) 0.65882(4) 0.25304(14) 0.0376(3) Uani 1 1 d . . . . .
C10B C 0.58819(18) 0.40609(5) 0.35825(18) 0.0203(4) Uani 1 1 d . . . . .
C3B C 0.62528(19) 0.36563(5) 0.54665(18) 0.0219(4) Uani 1 1 d . . . . .
H3BA H 0.5379 0.3663 0.5735 0.026 Uiso 1 1 calc R . . . .
H3BB H 0.6770 0.3440 0.5872 0.026 Uiso 1 1 calc R . . . .
C5B C 0.64472(18) 0.42593(5) 0.47398(18) 0.0201(4) Uani 1 1 d . . . . .
C4B C 0.70700(18) 0.40079(5) 0.58975(18) 0.0202(4) Uani 1 1 d . . . . .
H4B H 0.8024 0.3960 0.5848 0.024 Uiso 1 1 calc R . . . .
C5 C 0.78894(17) 0.58786(5) 0.27897(18) 0.0205(4) Uani 1 1 d . . . . .
C4 C 0.79173(18) 0.59884(5) 0.42305(18) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.6963 0.6034 0.4286 0.026 Uiso 1 1 calc R . . . .
C10 C 0.80011(18) 0.61822(5) 0.20155(19) 0.0215(4) Uani 1 1 d . . . . .
C17 C 0.85220(19) 0.57110(5) 0.53038(18) 0.0213(4) Uani 1 1 d . . . . .
C11 C 0.6822(2) 0.67361(5) 0.27374(19) 0.0232(4) Uani 1 1 d . . . . .
C2B C 0.60257(18) 0.36544(5) 0.38982(18) 0.0209(4) Uani 1 1 d . . . . .
C9 C 0.79609(19) 0.61482(6) 0.0643(2) 0.0258(4) Uani 1 1 d . . . . .
H9 H 0.8012 0.6357 0.0108 0.031 Uiso 1 1 calc R . . . .
C2 C 0.81576(19) 0.65230(5) 0.28836(19) 0.0226(4) Uani 1 1 d . . . . .
C3 C 0.8643(2) 0.63597(5) 0.43303(19) 0.0237(4) Uani 1 1 d . . . . .
H3A H 0.9639 0.6329 0.4575 0.028 Uiso 1 1 calc R . . . .
H3B H 0.8376 0.6517 0.5011 0.028 Uiso 1 1 calc R . . . .
C12 C 0.5661(2) 0.66403(5) 0.17728(19) 0.0242(4) Uani 1 1 d . . . . .
H12 H 0.5693 0.6442 0.1183 0.029 Uiso 1 1 calc R . . . .
C8B C 0.52143(19) 0.46142(5) 0.2367(2) 0.0246(4) Uani 1 1 d . . . . .
H8B H 0.4802 0.4738 0.1556 0.030 Uiso 1 1 calc R . . . .
C22B C 0.59345(19) 0.42279(5) 0.77157(19) 0.0235(4) Uani 1 1 d . . . . .
H22B H 0.5081 0.4172 0.7135 0.028 Uiso 1 1 calc R . . . .
C6 C 0.77676(19) 0.55339(5) 0.2213(2) 0.0237(4) Uani 1 1 d . . . . .
H6 H 0.7695 0.5326 0.2743 0.028 Uiso 1 1 calc R . . . .
C16 C 0.6759(2) 0.70292(6) 0.3594(2) 0.0288(4) Uani 1 1 d . . . . .
H16 H 0.7541 0.7094 0.4268 0.035 Uiso 1 1 calc R . . . .
C17B C 0.71130(19) 0.41583(5) 0.72891(18) 0.0208(4) Uani 1 1 d . . . . .
C22 C 0.77380(19) 0.55592(5) 0.61187(19) 0.0221(4) Uani 1 1 d . . . . .
H22 H 0.6825 0.5634 0.6012 0.027 Uiso 1 1 calc R . . . .
C1B C 0.4717(2) 0.34574(5) 0.3230(2) 0.0244(4) Uani 1 1 d . . . . .
C9B C 0.52796(19) 0.42356(5) 0.23775(19) 0.0233(4) Uani 1 1 d . . . . .
H9B H 0.4921 0.4100 0.1580 0.028 Uiso 1 1 calc R . . . .
C6B C 0.63865(19) 0.46367(5) 0.47269(19) 0.0224(4) Uani 1 1 d . . . . .
H6B H 0.6774 0.4772 0.5517 0.027 Uiso 1 1 calc R . . . .
C18 C 0.9855(2) 0.55941(6) 0.5478(2) 0.0274(4) Uani 1 1 d . . . . .
H18 H 1.0396 0.5691 0.4921 0.033 Uiso 1 1 calc R . . . .
C18B C 0.83513(19) 0.42493(6) 0.8156(2) 0.0256(4) Uani 1 1 d . . . . .
H18B H 0.9167 0.4206 0.7882 0.031 Uiso 1 1 calc R . . . .
C7B C 0.57485(19) 0.48122(5) 0.3536(2) 0.0246(4) Uani 1 1 d . . . . .
H7B H 0.5677 0.5069 0.3520 0.030 Uiso 1 1 calc R . . . .
C11B C 0.7231(2) 0.34750(6) 0.3481(2) 0.0257(4) Uani 1 1 d . . . . .
C21 C 0.8287(2) 0.52987(5) 0.70877(19) 0.0235(4) Uani 1 1 d . . . . .
H21 H 0.7744 0.5197 0.7636 0.028 Uiso 1 1 calc R . . . .
C19B C 0.8407(2) 0.44016(6) 0.9409(2) 0.0288(4) Uani 1 1 d . . . . .
H19B H 0.9258 0.4463 0.9982 0.035 Uiso 1 1 calc R . . . .
C21B C 0.5990(2) 0.43774(5) 0.8979(2) 0.0255(4) Uani 1 1 d . . . . .
H21B H 0.5178 0.4420 0.9261 0.031 Uiso 1 1 calc R . . . .
C8 C 0.78444(19) 0.58029(6) 0.0073(2) 0.0271(4) Uani 1 1 d . . . . .
H8 H 0.7827 0.5775 -0.0858 0.032 Uiso 1 1 calc R . . . .
C20 C 0.9619(2) 0.51870(5) 0.7256(2) 0.0260(4) Uani 1 1 d . . . . .
H20 H 0.9991 0.5009 0.7916 0.031 Uiso 1 1 calc R . . . .
C7 C 0.77536(19) 0.54982(6) 0.0850(2) 0.0270(4) Uani 1 1 d . . . . .
H7 H 0.7681 0.5264 0.0449 0.032 Uiso 1 1 calc R . . . .
C12B C 0.8009(2) 0.36626(6) 0.2755(2) 0.0284(4) Uani 1 1 d . . . . .
H12B H 0.7780 0.3906 0.2483 0.034 Uiso 1 1 calc R . . . .
C20B C 0.7232(2) 0.44648(5) 0.98324(19) 0.0264(4) Uani 1 1 d . . . . .
H20B H 0.7273 0.4567 1.0697 0.032 Uiso 1 1 calc R . . . .
C13 C 0.4449(2) 0.68296(6) 0.1655(2) 0.0277(4) Uani 1 1 d . . . . .
C19 C 1.0404(2) 0.53377(6) 0.6452(2) 0.0296(4) Uani 1 1 d . . . . .
H19 H 1.1320 0.5265 0.6568 0.035 Uiso 1 1 calc R . . . .
C16B C 0.7585(2) 0.31149(6) 0.3875(2) 0.0325(5) Uani 1 1 d . . . . .
H16B H 0.7068 0.2986 0.4384 0.039 Uiso 1 1 calc R . . . .
C15 C 0.5568(2) 0.72278(6) 0.3475(2) 0.0312(5) Uani 1 1 d . . . . .
C1 C 0.9236(2) 0.67695(6) 0.2551(2) 0.0293(4) Uani 1 1 d . . . . .
C13B C 0.9129(2) 0.34976(7) 0.2419(2) 0.0355(5) Uani 1 1 d . . . . .
C14 C 0.4426(2) 0.71226(6) 0.2505(2) 0.0309(5) Uani 1 1 d . . . . .
H14 H 0.3608 0.7255 0.2422 0.037 Uiso 1 1 calc R . . . .
C14B C 0.9433(2) 0.31386(7) 0.2799(3) 0.0411(6) Uani 1 1 d . . . . .
H14B H 1.0174 0.3023 0.2551 0.049 Uiso 1 1 calc R . . . .
C15B C 0.8681(2) 0.29449(7) 0.3531(3) 0.0394(6) Uani 1 1 d . . . . .
C23 C 0.3199(2) 0.67146(7) 0.0610(2) 0.0358(5) Uani 1 1 d . . . . .
H23D H 0.3164 0.6844 -0.0238 0.054 Uiso 1 1 calc GR . . . .
H23E H 0.2391 0.6773 0.0934 0.054 Uiso 1 1 calc GR . . . .
H23F H 0.3233 0.6453 0.0456 0.054 Uiso 1 1 calc GR . . . .
C24 C 0.5527(3) 0.75501(6) 0.4384(3) 0.0424(6) Uani 1 1 d . . . . .
H24D H 0.6117 0.7504 0.5278 0.064 Uiso 1 1 calc GR . . . .
H24E H 0.4597 0.7588 0.4469 0.064 Uiso 1 1 calc GR . . . .
H24F H 0.5840 0.7767 0.3994 0.064 Uiso 1 1 calc GR . . . .
C23B C 0.9978(3) 0.36997(8) 0.1672(3) 0.0486(6) Uani 1 1 d . . . . .
H23A H 0.9598 0.3674 0.0698 0.073 Uiso 1 1 calc GR . . . .
H23B H 1.0901 0.3602 0.1903 0.073 Uiso 1 1 calc GR . . . .
H23C H 0.9998 0.3957 0.1919 0.073 Uiso 1 1 calc GR . . . .
C24B C 0.9049(3) 0.25564(8) 0.3995(4) 0.0592(8) Uani 1 1 d . . . . .
H24A H 0.8569 0.2489 0.4687 0.089 Uiso 1 1 calc GR . . . .
H24B H 1.0027 0.2539 0.4372 0.089 Uiso 1 1 calc GR . . . .
H24C H 0.8786 0.2391 0.3223 0.089 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
F2B C1B 1.348(2) . ?
F1B C1B 1.350(2) . ?
F3B C1B 1.344(2) . ?
F3 C1 1.351(2) . ?
F2 C1 1.344(2) . ?
F1 C1 1.349(3) . ?
C10B C5B 1.391(3) . ?
C10B C2B 1.532(3) . ?
C10B C9B 1.393(3) . ?
C3B C4B 1.546(3) . ?
C3B C2B 1.560(2) . ?
C5B C4B 1.516(2) . ?
C5B C6B 1.392(3) . ?
C4B C17B 1.514(3) . ?
C5 C4 1.517(3) . ?
C5 C10 1.389(3) . ?
C5 C6 1.393(3) . ?
C4 C17 1.517(3) . ?
C4 C3 1.546(3) . ?
C10 C9 1.395(3) . ?
C10 C2 1.523(3) . ?
C17 C22 1.398(3) . ?
C17 C18 1.393(3) . ?
C11 C2 1.546(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.400(3) . ?
C2B C1B 1.527(3) . ?
C2B C11B 1.539(3) . ?
C9 C8 1.392(3) . ?
C2 C3 1.560(3) . ?
C2 C1 1.523(3) . ?
C12 C13 1.397(3) . ?
C8B C9B 1.397(3) . ?
C8B C7B 1.392(3) . ?
C22B C17B 1.393(3) . ?
C22B C21B 1.389(3) . ?
C6 C7 1.392(3) . ?
C16 C15 1.396(3) . ?
C17B C18B 1.397(3) . ?
C22 C21 1.395(3) . ?
C6B C7B 1.393(3) . ?
C18 C19 1.388(3) . ?
C18B C19B 1.383(3) . ?
C11B C12B 1.389(3) . ?
C11B C16B 1.408(3) . ?
C21 C20 1.387(3) . ?
C19B C20B 1.384(3) . ?
C21B C20B 1.391(3) . ?
C8 C7 1.390(3) . ?
C20 C19 1.389(3) . ?
C12B C13B 1.404(3) . ?
C13 C14 1.388(3) . ?
C13 C23 1.512(3) . ?
C16B C15B 1.393(3) . ?
C15 C14 1.391(3) . ?
C15 C24 1.513(3) . ?
C13B C14B 1.393(4) . ?
C13B C23B 1.481(4) . ?
C14B C15B 1.387(4) . ?
C15B C24B 1.526(4) . ?

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
C5B C10B C2B 109.64(16) . . ?
C5B C10B C9B 120.79(17) . . ?
C9B C10B C2B 129.56(17) . . ?
C4B C3B C2B 103.52(15) . . ?
C10B C5B C4B 110.58(16) . . ?
C10B C5B C6B 120.56(17) . . ?
C6B C5B C4B 128.86(17) . . ?
C5B C4B C3B 101.17(14) . . ?
C17B C4B C3B 117.85(16) . . ?
C17B C4B C5B 114.81(15) . . ?
C10 C5 C4 110.48(16) . . ?
C10 C5 C6 120.39(17) . . ?
C6 C5 C4 129.13(17) . . ?
C5 C4 C3 101.45(15) . . ?
C17 C4 C5 115.45(16) . . ?
C17 C4 C3 116.30(15) . . ?
C5 C10 C9 120.69(18) . . ?
C5 C10 C2 110.21(16) . . ?
C9 C10 C2 129.10(18) . . ?
C22 C17 C4 120.50(17) . . ?
C18 C17 C4 121.06(17) . . ?
C18 C17 C22 118.42(17) . . ?
C12 C11 C2 121.25(17) . . ?
C12 C11 C16 118.68(18) . . ?
C16 C11 C2 120.07(17) . . ?
C10B C2B C3B 101.22(14) . . ?
C10B C2B C11B 113.87(16) . . ?
C1B C2B C10B 109.97(15) . . ?
C1B C2B C3B 111.14(16) . . ?
C1B C2B C11B 109.84(15) . . ?
C11B C2B C3B 110.56(15) . . ?
C8 C9 C10 118.68(18) . . ?
C10 C2 C11 113.24(15) . . ?
C10 C2 C3 101.37(15) . . ?
C10 C2 C1 110.12(16) . . ?
C11 C2 C3 111.16(16) . . ?
C1 C2 C11 109.80(16) . . ?
C1 C2 C3 110.92(15) . . ?
C4 C3 C2 103.87(14) . . ?
C11 C12 C13 121.21(19) . . ?
C7B C8B C9B 120.58(18) . . ?
C21B C22B C17B 120.92(17) . . ?
C7 C6 C5 119.08(19) . . ?
C15 C16 C11 121.19(19) . . ?
C22B C17B C4B 121.63(16) . . ?
C22B C17B C18B 118.16(17) . . ?
C18B C17B C4B 120.13(17) . . ?
C21 C22 C17 120.49(18) . . ?
F2B C1B F1B 106.23(15) . . ?
F2B C1B C2B 112.16(16) . . ?
F1B C1B C2B 112.11(15) . . ?
F3B C1B F2B 106.45(15) . . ?
F3B C1B F1B 105.85(16) . . ?
F3B C1B C2B 113.51(16) . . ?
C10B C9B C8B 118.57(18) . . ?
C5B C6B C7B 118.86(17) . . ?
C19 C18 C17 121.04(19) . . ?
C19B C18B C17B 120.97(18) . . ?
C8B C7B C6B 120.59(18) . . ?
C12B C11B C2B 121.68(18) . . ?
C12B C11B C16B 118.78(19) . . ?
C16B C11B C2B 119.52(19) . . ?
C20 C21 C22 120.43(18) . . ?
C18B C19B C20B 120.47(18) . . ?
C22B C21B C20B 120.16(18) . . ?
C7 C8 C9 120.72(18) . . ?
C21 C20 C19 119.32(18) . . ?
C8 C7 C6 120.42(19) . . ?
C11B C12B C13B 120.8(2) . . ?
C19B C20B C21B 119.31(18) . . ?
C12 C13 C23 119.87(19) . . ?
C14 C13 C12 118.68(19) . . ?
C14 C13 C23 121.44(19) . . ?
C18 C19 C20 120.29(19) . . ?
C15B C16B C11B 121.2(2) . . ?
C16 C15 C24 120.6(2) . . ?
C14 C15 C16 118.48(19) . . ?
C14 C15 C24 121.0(2) . . ?
F3 C1 C2 111.96(16) . . ?
F2 C1 F3 106.36(17) . . ?
F2 C1 F1 105.91(16) . . ?
F2 C1 C2 113.43(17) . . ?
F1 C1 F3 106.37(17) . . ?
F1 C1 C2 112.29(17) . . ?
C12B C13B C23B 120.9(2) . . ?
C14B C13B C12B 118.9(2) . . ?
C14B C13B C23B 120.2(2) . . ?
C13 C14 C15 121.7(2) . . ?
C15B C14B C13B 121.6(2) . . ?
C16B C15B C24B 119.7(3) . . ?
C14B C15B C16B 118.7(2) . . ?
C14B C15B C24B 121.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.285
####################################################################### 
# 
# 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_7072-9926_b-45
_database_code_depnum_ccdc_archive 'CCDC 1875119'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;SPBU
Russia
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 F3 O2'
_chemical_formula_sum            'C25 H23 F3 O2'
_chemical_formula_weight         412.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.5733(2)
_cell_length_b                   18.7290(4)
_cell_length_c                   19.4741(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.635(2)
_cell_angle_gamma                90
_cell_volume                     4064.92(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20069
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7690
_cell_measurement_theta_min      3.9070
_shelx_estimated_absorpt_T_max   0.759
_shelx_estimated_absorpt_T_min   0.720
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1728
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.34
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38593
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.049
_diffrn_reflns_theta_min         3.335
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_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    -31.00  13.00   0.50    0.20    --  -41.22 106.00  -9.00   88
  2  ω    -75.00 -37.00   0.50    0.20    --  -41.22 106.00  -9.00   76
  3  ω     82.00 154.00   0.50    0.45    --  101.00 106.00  -9.00  144
  4  ω     54.00 100.00   0.50    0.45    --  101.00-106.00-108.00   92
  5  ω    -55.00 -13.00   0.50    0.20    --  -41.22 138.00-120.00   84
  6  ω    -41.00   5.00   0.50    0.20    --  -41.22  43.00   0.00   92
  7  ω    -91.00 -65.00   0.50    0.20    --  -41.22 138.00-120.00   52
  8  ω   -103.00 -33.00   0.50    0.20    --  -41.22 -32.00-150.00  140
  9  ω    -95.00 -35.00   0.50    0.20    --  -41.22 -32.00 120.00  120
 10  ω    -58.00  13.00   0.50    0.20    --  -41.22  54.00-150.00  142
 11  ω     31.00  56.00   0.50    0.20    --   41.22  43.00  30.00   50
 12  ω     65.00  97.00   0.50    0.20    --   41.22  43.00  30.00   64
 13  ω     23.00 101.00   0.50    0.20    --   41.22  65.00 -30.00  156
 14  ω    -13.00  17.00   0.50    0.20    --   41.22-104.00-150.00   60
 15  ω    -16.00  25.00   0.50    0.20    --   41.22 -32.00  90.00   82
 16  ω     22.00  47.00   0.50    0.20    --   41.22-106.00-108.00   50
 17  ω     29.00  54.00   0.50    0.20    --   41.22  43.00  60.00   50
 18  ω     25.00  71.00   0.50    0.20    --   41.22-104.00-150.00   92
 19  ω     45.00 109.00   0.50    0.45    --  101.00 -25.00-120.00  128
 20  ω     86.00 120.00   0.50    0.45    --  101.00 -59.00 -90.00   68
 21  ω     37.00 119.00   0.50    0.45    --  101.00 -77.00-120.00  164
 22  ω     53.00 109.00   0.50    0.45    --  101.00 -33.00-180.00  112
 23  ω     98.00 123.00   0.50    0.45    --  101.00 -68.00   0.00   50
 24  ω     93.00 123.00   0.50    0.45    --  101.00 -87.00 -90.00   60
 25  ω    116.00 141.00   0.50    0.45    --  101.00  33.00 -30.00   50
 26  ω     53.00  79.00   0.50    0.45    --  101.00 -87.00 -90.00   52
 27  ω     92.00 157.00   0.50    0.45    --  101.00  25.00 -90.00  130
 28  ω     37.00 110.00   0.50    0.45    --  101.00 -33.00   0.00  146
 29  ω     31.00 108.00   0.50    0.45    --  101.00 -17.00   0.00  154
 30  ω     53.00  79.00   0.50    0.45    --  101.00 -59.00 -90.00   52
 31  ω     39.00 113.00   0.50    0.45    --  101.00 -50.00  90.00  148
 32  ω     85.00 157.00   0.50    0.45    --  101.00  68.00-180.00  144
 33  ω     88.00 114.00   0.50    0.45    --  101.00-111.00 -60.00   52
 34  ω     35.00 127.00   0.50    0.45    --  101.00 -93.00  60.00  184
 35  ω     33.00  59.00   0.50    0.20    --   41.22-106.00-108.00   52
 36  ω    -50.00 -25.00   0.50    0.20    --  -41.22  21.00 -30.00   50
 37  ω    -87.00 -37.00   0.50    0.20    --  -41.22 -32.00 150.00  100
 38  ω     82.00 107.00   0.50    0.20    --   41.22  32.00 -60.00   50
 39  ω     24.00  49.00   0.50    0.20    --   41.22 -32.00 -90.00   50
 40  ω     34.00  59.00   0.50    0.20    --   41.22 -54.00-150.00   50
 41  ω    -23.00   3.00   0.50    0.20    --   41.22 -32.00 -90.00   52
 42  ω     -4.00  49.00   0.50    0.20    --   41.22 -32.00-180.00  106
 43  ω     43.00  69.00   0.50    0.20    --   41.22  32.00  90.00   52
 44  ω     99.00 146.00   0.50    0.45    --  101.00  50.00-150.00   94
 45  ω     77.00 124.00   0.50    0.45    --  101.00  77.00 150.00   94
 46  ω     93.00 118.00   0.50    0.45    --  101.00 -68.00 -30.00   50
 47  ω    130.00 155.00   0.50    0.45    --  101.00  77.00 150.00   50
 48  ω     51.00 121.00   0.50    0.45    --  101.00-133.00  90.00  140
 49  ω     51.00 109.00   0.50    0.45    --  101.00-111.00-120.00  116
 50  ω    101.00 156.00   0.50    0.45    --  101.00  25.00 150.00  110
 51  ω     39.00 119.00   0.50    0.45    --  101.00 -77.00  90.00  160
 52  ω     89.00 114.00   0.50    0.45    --  101.00 -17.00-120.00   50
 53  ω     88.00 124.00   0.50    0.45    --  101.00-133.00-120.00   72
 54  ω     64.00 104.00   0.50    0.45    --  101.00 -42.00 -90.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0963501000
_diffrn_orient_matrix_UB_12      -0.0408592000
_diffrn_orient_matrix_UB_13      -0.0254265000
_diffrn_orient_matrix_UB_21      0.0291614000
_diffrn_orient_matrix_UB_22      0.0683790000
_diffrn_orient_matrix_UB_23      -0.0360656000
_diffrn_orient_matrix_UB_31      0.0947591000
_diffrn_orient_matrix_UB_32      0.0205458000
_diffrn_orient_matrix_UB_33      0.0692708000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7021
_reflns_number_total             7965
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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         0.230
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7965
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+1.0699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0928
_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:
 C31(H31), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C47(H47), C20(H20), C51(H51), C8(H8), C5(H5), C17(H17), C6(H6),
 C38(H38), C45(H45), C11(H11), C44(H44), C50(H50), C41(H41), C14(H14), C12(H12),
  C15(H15), C35(H35), C43(H43), C42(H42), C36(H36), C13(H13)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C55(H55A,H55B,H55C), C25(H25A,H25B,H25C), C60(H60A,H60B,
 H60C), C53(H53A,H53B,H53C), C23(H23A,H23B,H23C)
;
_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
F27 F 0.87226(7) 0.32989(4) 0.70665(4) 0.03028(18) Uani 1 1 d . . . . .
F28 F 0.69653(7) 0.32698(4) 0.63223(4) 0.03016(18) Uani 1 1 d . . . . .
F57 F 0.61870(7) 0.45508(4) 0.72464(4) 0.03215(18) Uani 1 1 d . . . . .
F58 F 0.54452(7) 0.35691(4) 0.75252(4) 0.03292(19) Uani 1 1 d . . . . .
F29 F 0.83643(7) 0.25712(4) 0.61760(4) 0.02904(17) Uani 1 1 d . . . . .
F59 F 0.72863(7) 0.38510(5) 0.80400(5) 0.03512(19) Uani 1 1 d . . . . .
O54 O 0.92295(8) 0.66810(5) 0.95338(5) 0.02476(19) Uani 1 1 d . . . . .
O24 O 0.62709(8) 0.33540(5) 0.29491(5) 0.0267(2) Uani 1 1 d . . . . .
O52 O 0.77159(8) 0.68821(5) 0.82936(5) 0.0254(2) Uani 1 1 d . . . . .
O22 O 0.50106(8) 0.38351(5) 0.37501(5) 0.0283(2) Uani 1 1 d . . . . .
C21 C 0.85850(11) 0.33727(6) 0.46847(7) 0.0197(2) Uani 1 1 d . . . . .
H21 H 0.9406 0.3256 0.4884 0.024 Uiso 1 1 calc R . . . .
C47 C 0.67657(11) 0.57250(7) 0.83286(7) 0.0222(3) Uani 1 1 d . . . . .
H47 H 0.6223 0.5796 0.7872 0.027 Uiso 1 1 calc R . . . .
C9 C 1.01840(11) 0.46002(6) 0.60250(6) 0.0189(2) Uani 1 1 d . . . . .
C48 C 0.76070(11) 0.62466(7) 0.86150(7) 0.0217(2) Uani 1 1 d . . . . .
C4 C 0.98851(11) 0.38818(6) 0.60702(6) 0.0190(2) Uani 1 1 d . . . . .
C39 C 0.45696(11) 0.42187(6) 0.91679(7) 0.0211(2) Uani 1 1 d . . . . .
C7 C 1.22533(11) 0.42727(7) 0.61748(6) 0.0219(3) Uani 1 1 d . . . . .
C20 C 0.80619(11) 0.32540(6) 0.39566(7) 0.0209(2) Uani 1 1 d . . . . .
H20 H 0.8529 0.3058 0.3670 0.025 Uiso 1 1 calc R . . . .
C40 C 0.26616(11) 0.49352(7) 0.86213(6) 0.0208(2) Uani 1 1 d . . . . .
C16 C 0.79330(11) 0.36551(6) 0.51180(6) 0.0189(2) Uani 1 1 d . . . . .
C49 C 0.84230(10) 0.61408(7) 0.92936(7) 0.0215(2) Uani 1 1 d . . . . .
C10 C 0.91508(10) 0.58097(6) 0.61609(6) 0.0196(2) Uani 1 1 d . . . . .
C51 C 0.75086(11) 0.49967(7) 0.93692(7) 0.0222(3) Uani 1 1 d . . . . .
H51 H 0.7477 0.4572 0.9630 0.027 Uiso 1 1 calc R . . . .
C2 C 0.81929(11) 0.45681(6) 0.61248(7) 0.0216(2) Uani 1 1 d . . . . .
H2A H 0.7346 0.4685 0.5884 0.026 Uiso 1 1 calc R . . . .
H2B H 0.8324 0.4609 0.6647 0.026 Uiso 1 1 calc R . . . .
C8 C 1.13603(11) 0.47990(6) 0.60774(6) 0.0204(2) Uani 1 1 d . . . . .
H8 H 1.1559 0.5288 0.6047 0.025 Uiso 1 1 calc R . . . .
C46 C 0.67041(10) 0.50911(7) 0.87051(7) 0.0211(2) Uani 1 1 d . . . . .
C31 C 0.40147(11) 0.48831(6) 0.87626(7) 0.0212(2) Uani 1 1 d . . . . .
H31 H 0.4383 0.5311 0.9044 0.025 Uiso 1 1 calc R . . . .
C32 C 0.44849(11) 0.48356(7) 0.80928(7) 0.0225(3) Uani 1 1 d . . . . .
H32A H 0.4518 0.5314 0.7883 0.027 Uiso 1 1 calc R . . . .
H32B H 0.3970 0.4520 0.7728 0.027 Uiso 1 1 calc R . . . .
C3 C 0.85227(11) 0.38099(6) 0.59157(6) 0.0198(2) Uani 1 1 d . . . . .
C18 C 0.61843(11) 0.36952(6) 0.40929(7) 0.0215(2) Uani 1 1 d . . . . .
C5 C 1.07656(11) 0.33560(6) 0.61941(6) 0.0216(2) Uani 1 1 d . . . . .
H5 H 1.0569 0.2869 0.6241 0.026 Uiso 1 1 calc R . . . .
C17 C 0.67099(11) 0.38109(6) 0.48125(7) 0.0209(2) Uani 1 1 d . . . . .
H17 H 0.6241 0.3997 0.5103 0.025 Uiso 1 1 calc R . . . .
C34 C 0.55629(11) 0.39983(7) 0.89459(7) 0.0224(3) Uani 1 1 d . . . . .
C6 C 1.19476(11) 0.35616(7) 0.62479(6) 0.0226(3) Uani 1 1 d . . . . .
H6 H 1.2559 0.3208 0.6337 0.027 Uiso 1 1 calc R . . . .
C1 C 0.90605(10) 0.50597(6) 0.58620(6) 0.0194(2) Uani 1 1 d . . . . .
H1 H 0.8753 0.5097 0.5332 0.023 Uiso 1 1 calc R . . . .
C38 C 0.42102(11) 0.38469(7) 0.96908(7) 0.0233(3) Uani 1 1 d . . . . .
H38 H 0.3535 0.4005 0.9839 0.028 Uiso 1 1 calc R . . . .
C45 C 0.21376(11) 0.55425(7) 0.88212(6) 0.0220(2) Uani 1 1 d . . . . .
H45 H 0.2629 0.5937 0.9022 0.026 Uiso 1 1 calc R . . . .
C19 C 0.68674(11) 0.34210(6) 0.36533(7) 0.0207(2) Uani 1 1 d . . . . .
C11 C 0.86354(11) 0.63794(7) 0.57251(7) 0.0233(3) Uani 1 1 d . . . . .
H11 H 0.8267 0.6298 0.5233 0.028 Uiso 1 1 calc R . . . .
C44 C 0.09033(12) 0.55796(7) 0.87305(7) 0.0253(3) Uani 1 1 d . . . . .
H44 H 0.0560 0.5998 0.8870 0.030 Uiso 1 1 calc R . . . .
C26 C 0.81466(11) 0.32397(7) 0.63670(7) 0.0237(3) Uani 1 1 d . . . . .
C33 C 0.57680(11) 0.45140(7) 0.83810(7) 0.0226(3) Uani 1 1 d . . . . .
C50 C 0.83653(11) 0.55166(7) 0.96612(7) 0.0224(3) Uani 1 1 d . . . . .
H50 H 0.8912 0.5441 1.0116 0.027 Uiso 1 1 calc R . . . .
C41 C 0.19170(11) 0.43674(7) 0.83129(7) 0.0251(3) Uani 1 1 d . . . . .
H41 H 0.2256 0.3953 0.8164 0.030 Uiso 1 1 calc R . . . .
C14 C 0.97096(12) 0.66311(7) 0.71565(7) 0.0275(3) Uani 1 1 d . . . . .
H14 H 1.0079 0.6715 0.7648 0.033 Uiso 1 1 calc R . . . .
C12 C 0.86517(12) 0.70686(7) 0.60006(8) 0.0275(3) Uani 1 1 d . . . . .
H12 H 0.8298 0.7452 0.5697 0.033 Uiso 1 1 calc R . . . .
C15 C 0.96984(12) 0.59461(7) 0.68805(7) 0.0248(3) Uani 1 1 d . . . . .
H15 H 1.0067 0.5566 0.7185 0.030 Uiso 1 1 calc R . . . .
C35 C 0.62090(11) 0.33987(7) 0.92533(7) 0.0262(3) Uani 1 1 d . . . . .
H35 H 0.6891 0.3246 0.9109 0.031 Uiso 1 1 calc R . . . .
C37 C 0.48438(12) 0.32373(7) 1.00004(7) 0.0254(3) Uani 1 1 d . . . . .
C43 C 0.01730(11) 0.50076(7) 0.84373(7) 0.0262(3) Uani 1 1 d . . . . .
H43 H -0.0667 0.5029 0.8384 0.031 Uiso 1 1 calc R . . . .
C42 C 0.06806(12) 0.44035(7) 0.82218(7) 0.0264(3) Uani 1 1 d . . . . .
H42 H 0.0184 0.4014 0.8012 0.032 Uiso 1 1 calc R . . . .
C56 C 0.61663(12) 0.41229(7) 0.77997(7) 0.0273(3) Uani 1 1 d . . . . .
C36 C 0.58407(12) 0.30263(7) 0.97754(7) 0.0266(3) Uani 1 1 d . . . . .
H36 H 0.6280 0.2616 0.9985 0.032 Uiso 1 1 calc R . . . .
C13 C 0.91845(12) 0.71933(7) 0.67187(8) 0.0287(3) Uani 1 1 d . . . . .
H13 H 0.9190 0.7661 0.6909 0.034 Uiso 1 1 calc R . . . .
C30 C 1.35066(12) 0.44673(8) 0.61493(8) 0.0285(3) Uani 1 1 d . . . . .
H30A H 1.3501 0.4587 0.5658 0.043 Uiso 1 1 calc GR . . . .
H30B H 1.4045 0.4062 0.6314 0.043 Uiso 1 1 calc GR . . . .
H30C H 1.3788 0.4880 0.6458 0.043 Uiso 1 1 calc GR . . . .
C55 C 1.01122(12) 0.65546(7) 1.01957(7) 0.0292(3) Uani 1 1 d . . . . .
H55A H 1.0549 0.6114 1.0161 0.044 Uiso 1 1 calc GR . . . .
H55B H 0.9715 0.6508 1.0579 0.044 Uiso 1 1 calc GR . . . .
H55C H 1.0676 0.6956 1.0300 0.044 Uiso 1 1 calc GR . . . .
C25 C 0.69570(13) 0.31049(9) 0.24864(7) 0.0339(3) Uani 1 1 d . . . . .
H25A H 0.6438 0.3070 0.1998 0.051 Uiso 1 1 calc GR . . . .
H25B H 0.7291 0.2634 0.2646 0.051 Uiso 1 1 calc GR . . . .
H25C H 0.7612 0.3440 0.2498 0.051 Uiso 1 1 calc GR . . . .
C60 C 0.44353(13) 0.28151(8) 1.05531(8) 0.0337(3) Uani 1 1 d . . . . .
H60A H 0.4411 0.3128 1.0952 0.050 Uiso 1 1 calc GR . . . .
H60B H 0.4997 0.2422 1.0727 0.050 Uiso 1 1 calc GR . . . .
H60C H 0.3633 0.2621 1.0339 0.050 Uiso 1 1 calc GR . . . .
C53 C 0.68833(13) 0.70163(8) 0.76134(7) 0.0312(3) Uani 1 1 d . . . . .
H53A H 0.6988 0.6656 0.7270 0.047 Uiso 1 1 calc GR . . . .
H53B H 0.7031 0.7492 0.7446 0.047 Uiso 1 1 calc GR . . . .
H53C H 0.6062 0.6992 0.7660 0.047 Uiso 1 1 calc GR . . . .
C23 C 0.42621(12) 0.40712(9) 0.41760(9) 0.0375(3) Uani 1 1 d . . . . .
H23A H 0.3442 0.4137 0.3875 0.056 Uiso 1 1 calc GR . . . .
H23B H 0.4565 0.4526 0.4403 0.056 Uiso 1 1 calc GR . . . .
H23C H 0.4263 0.3714 0.4544 0.056 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
F27 C26 1.3501(14) . ?
F28 C26 1.3475(15) . ?
F57 C56 1.3482(16) . ?
F58 C56 1.3481(15) . ?
F29 C26 1.3489(15) . ?
F59 C56 1.3533(15) . ?
O54 C49 1.3705(15) . ?
O54 C55 1.4323(16) . ?
O24 C19 1.3648(15) . ?
O24 C25 1.4303(17) . ?
O52 C48 1.3662(15) . ?
O52 C53 1.4347(15) . ?
O22 C18 1.3677(15) . ?
O22 C23 1.4218(17) . ?
C21 H21 0.9500 . ?
C21 C20 1.4013(17) . ?
C21 C16 1.3800(17) . ?
C47 H47 0.9500 . ?
C47 C48 1.3860(17) . ?
C47 C46 1.4072(18) . ?
C9 C4 1.3980(17) . ?
C9 C8 1.3883(17) . ?
C9 C1 1.5198(16) . ?
C48 C49 1.4159(18) . ?
C4 C3 1.5293(16) . ?
C4 C5 1.3907(17) . ?
C39 C31 1.5200(17) . ?
C39 C34 1.3953(17) . ?
C39 C38 1.3868(18) . ?
C7 C8 1.4036(17) . ?
C7 C6 1.3951(18) . ?
C7 C30 1.5093(17) . ?
C20 H20 0.9500 . ?
C20 C19 1.3848(17) . ?
C40 C31 1.5183(16) . ?
C40 C45 1.3929(17) . ?
C40 C41 1.3983(18) . ?
C16 C3 1.5464(16) . ?
C16 C17 1.4103(17) . ?
C49 C50 1.3818(18) . ?
C10 C1 1.5134(16) . ?
C10 C11 1.3934(17) . ?
C10 C15 1.3971(17) . ?
C51 H51 0.9500 . ?
C51 C46 1.3862(18) . ?
C51 C50 1.3967(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5530(16) . ?
C2 C1 1.5474(16) . ?
C8 H8 0.9500 . ?
C46 C33 1.5401(17) . ?
C31 H31 1.0000 . ?
C31 C32 1.5454(17) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.5600(16) . ?
C3 C26 1.5195(17) . ?
C18 C17 1.3861(18) . ?
C18 C19 1.4093(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3975(18) . ?
C17 H17 0.9500 . ?
C34 C33 1.5297(18) . ?
C34 C35 1.3920(18) . ?
C6 H6 0.9500 . ?
C1 H1 1.0000 . ?
C38 H38 0.9500 . ?
C38 C37 1.4024(18) . ?
C45 H45 0.9500 . ?
C45 C44 1.3932(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3960(19) . ?
C44 H44 0.9500 . ?
C44 C43 1.3885(19) . ?
C33 C56 1.5204(18) . ?
C50 H50 0.9500 . ?
C41 H41 0.9500 . ?
C41 C42 1.3953(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3897(18) . ?
C14 C13 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(2) . ?
C15 H15 0.9500 . ?
C35 H35 0.9500 . ?
C35 C36 1.391(2) . ?
C37 C36 1.3970(19) . ?
C37 C60 1.511(2) . ?
C43 H43 0.9500 . ?
C43 C42 1.3908(19) . ?
C42 H42 0.9500 . ?
C36 H36 0.9500 . ?
C13 H13 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C49 O54 C55 116.11(10) . . ?
C19 O24 C25 116.52(10) . . ?
C48 O52 C53 116.98(10) . . ?
C18 O22 C23 117.12(10) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
C16 C21 C20 121.41(11) . . ?
C48 C47 H47 119.5 . . ?
C48 C47 C46 120.92(11) . . ?
C46 C47 H47 119.5 . . ?
C4 C9 C1 110.23(10) . . ?
C8 C9 C4 120.52(11) . . ?
C8 C9 C1 129.08(11) . . ?
O52 C48 C47 124.84(11) . . ?
O52 C48 C49 115.39(11) . . ?
C47 C48 C49 119.76(11) . . ?
C9 C4 C3 109.38(10) . . ?
C5 C4 C9 120.68(11) . . ?
C5 C4 C3 129.81(11) . . ?
C34 C39 C31 110.45(11) . . ?
C38 C39 C31 128.60(11) . . ?
C38 C39 C34 120.94(11) . . ?
C8 C7 C30 120.34(11) . . ?
C6 C7 C8 119.11(11) . . ?
C6 C7 C30 120.42(11) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 C21 120.34(11) . . ?
C19 C20 H20 119.8 . . ?
C45 C40 C31 120.49(11) . . ?
C45 C40 C41 118.47(11) . . ?
C41 C40 C31 121.00(11) . . ?
C21 C16 C3 121.34(11) . . ?
C21 C16 C17 118.25(11) . . ?
C17 C16 C3 120.40(11) . . ?
O54 C49 C48 115.90(11) . . ?
O54 C49 C50 124.84(11) . . ?
C50 C49 C48 119.26(11) . . ?
C11 C10 C1 120.17(11) . . ?
C11 C10 C15 118.36(11) . . ?
C15 C10 C1 121.41(11) . . ?
C46 C51 H51 119.5 . . ?
C46 C51 C50 121.03(12) . . ?
C50 C51 H51 119.5 . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C1 C2 C3 103.30(9) . . ?
C9 C8 C7 119.56(11) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C47 C46 C33 120.49(11) . . ?
C51 C46 C47 118.56(11) . . ?
C51 C46 C33 120.95(11) . . ?
C39 C31 H31 108.3 . . ?
C39 C31 C32 101.27(9) . . ?
C40 C31 C39 114.69(10) . . ?
C40 C31 H31 108.3 . . ?
C40 C31 C32 115.55(10) . . ?
C32 C31 H31 108.3 . . ?
C31 C32 H32A 111.0 . . ?
C31 C32 H32B 111.0 . . ?
C31 C32 C33 103.66(10) . . ?
H32A C32 H32B 109.0 . . ?
C33 C32 H32A 111.0 . . ?
C33 C32 H32B 111.0 . . ?
C4 C3 C16 111.51(10) . . ?
C4 C3 C2 100.44(9) . . ?
C16 C3 C2 111.21(10) . . ?
C26 C3 C4 112.89(10) . . ?
C26 C3 C16 109.36(10) . . ?
C26 C3 C2 111.23(10) . . ?
O22 C18 C17 124.82(11) . . ?
O22 C18 C19 114.79(11) . . ?
C17 C18 C19 120.39(11) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.34(11) . . ?
C6 C5 H5 120.8 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.75(11) . . ?
C18 C17 H17 119.6 . . ?
C39 C34 C33 109.66(11) . . ?
C35 C34 C39 119.83(12) . . ?
C35 C34 C33 130.49(12) . . ?
C7 C6 C5 121.69(12) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C9 C1 C2 100.89(9) . . ?
C9 C1 H1 107.5 . . ?
C10 C1 C9 118.60(10) . . ?
C10 C1 C2 114.12(10) . . ?
C10 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
C39 C38 H38 120.0 . . ?
C39 C38 C37 119.93(12) . . ?
C37 C38 H38 120.0 . . ?
C40 C45 H45 119.5 . . ?
C40 C45 C44 120.94(12) . . ?
C44 C45 H45 119.5 . . ?
O24 C19 C20 125.76(11) . . ?
O24 C19 C18 115.41(11) . . ?
C20 C19 C18 118.83(11) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.97(12) . . ?
C12 C11 H11 119.5 . . ?
C45 C44 H44 119.9 . . ?
C43 C44 C45 120.22(12) . . ?
C43 C44 H44 119.9 . . ?
F27 C26 C3 112.66(10) . . ?
F28 C26 F27 106.15(10) . . ?
F28 C26 F29 106.42(10) . . ?
F28 C26 C3 112.15(10) . . ?
F29 C26 F27 106.04(10) . . ?
F29 C26 C3 112.89(10) . . ?
C46 C33 C32 111.89(10) . . ?
C34 C33 C46 112.13(10) . . ?
C34 C33 C32 100.68(10) . . ?
C56 C33 C46 108.80(10) . . ?
C56 C33 C32 111.62(10) . . ?
C56 C33 C34 111.60(11) . . ?
C49 C50 C51 120.46(11) . . ?
C49 C50 H50 119.8 . . ?
C51 C50 H50 119.8 . . ?
C40 C41 H41 119.7 . . ?
C42 C41 C40 120.66(12) . . ?
C42 C41 H41 119.7 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.40(12) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.95(12) . . ?
C13 C12 H12 120.0 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.74(12) . . ?
C14 C15 H15 119.6 . . ?
C34 C35 H35 120.5 . . ?
C36 C35 C34 118.94(12) . . ?
C36 C35 H35 120.5 . . ?
C38 C37 C60 120.31(12) . . ?
C36 C37 C38 118.41(12) . . ?
C36 C37 C60 121.26(12) . . ?
C44 C43 H43 120.3 . . ?
C44 C43 C42 119.47(12) . . ?
C42 C43 H43 120.3 . . ?
C41 C42 H42 119.9 . . ?
C43 C42 C41 120.20(12) . . ?
C43 C42 H42 119.9 . . ?
F57 C56 F59 106.16(10) . . ?
F57 C56 C33 112.52(11) . . ?
F58 C56 F57 106.43(10) . . ?
F58 C56 F59 106.28(10) . . ?
F58 C56 C33 112.73(11) . . ?
F59 C56 C33 112.22(11) . . ?
C35 C36 C37 121.94(12) . . ?
C35 C36 H36 119.0 . . ?
C37 C36 H36 119.0 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.57(12) . . ?
C12 C13 H13 120.2 . . ?
C7 C30 H30A 109.5 . . ?
C7 C30 H30B 109.5 . . ?
C7 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O54 C55 H55A 109.5 . . ?
O54 C55 H55B 109.5 . . ?
O54 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
O24 C25 H25A 109.5 . . ?
O24 C25 H25B 109.5 . . ?
O24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C37 C60 H60A 109.5 . . ?
C37 C60 H60B 109.5 . . ?
C37 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
O52 C53 H53A 109.5 . . ?
O52 C53 H53B 109.5 . . ?
O52 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 1.174
_oxdiff_exptl_absorpt_empirical_full_min 0.755
