# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_exp_507
_database_code_depnum_ccdc_archive 'CCDC 2004999'
loop_
_audit_author_name
_audit_author_address
'Shujie Chen'
;Guangzhou University
China
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;
_audit_creation_date             2020-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H11 F3 O4'
_chemical_formula_sum            'C16 H11 F3 O4'
_chemical_formula_weight         324.25
_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                   6.53494(10)
_cell_length_b                   17.8693(2)
_cell_length_c                   19.2521(2)
_cell_angle_alpha                79.7570(10)
_cell_angle_beta                 88.3822(11)
_cell_angle_gamma                82.9770(10)
_cell_volume                     2195.69(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11080
_cell_measurement_temperature    302.1(2)
_cell_measurement_theta_max      74.2370
_cell_measurement_theta_min      2.3960
_cell_oxdiff_angle_alpha         79.7569(10)
_cell_oxdiff_angle_beta          88.3822(11)
_cell_oxdiff_angle_gamma         82.9771(12)
_cell_oxdiff_length_a            6.53494(10)
_cell_oxdiff_length_b            17.8693(2)
_cell_oxdiff_length_c            19.2521(2)
_cell_oxdiff_measurement_reflns_used 11080
_cell_oxdiff_volume              2195.69(5)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.981
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26076
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.975
_diffrn_reflns_theta_min         2.332
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.1(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -77.00 -21.00   0.50    0.15    --  -45.62 109.00 104.00  112
  2  ω      7.00  54.00   0.50    0.15    --   45.62-109.00   9.00   94
  3  ω    -69.00 -32.00   0.50    0.80    -- -102.00 109.00 104.00   74
  4  ω   -124.00 -95.00   0.50    0.80    -- -102.00-109.00   9.00   58
  5  ω     83.00 108.00   0.50    0.80    --  106.06-109.00   9.00   50
  6  ω     88.00 137.00   0.50    0.80    --  106.06 109.00 104.00   98
  7  ω    -24.00  13.00   0.50    0.15    --  -45.62  19.00 -60.00   74
  8  ω    -14.00  15.00   0.50    0.15    --   45.62 -57.00 -30.00   58
  9  ω     38.00 117.00   0.50    0.15    --   45.62  57.00  60.00  158
 10  ω    -24.00   2.00   0.50    0.15    --   45.62 -19.00-180.00   52
 11  ω     33.00 119.00   0.50    0.15    --   45.62  37.00 150.00  172
 12  ω     20.00  61.00   0.50    0.15    --   45.62 -57.00 -30.00   82
 13  ω    -26.00  33.00   0.50    0.15    --   45.62 -37.00 -90.00  118
 14  ω   -164.00-126.00   0.50    0.80    -- -102.00 -77.00  60.00   76
 15  ω   -169.00 -92.00   0.50    0.80    -- -102.00 -61.00  30.00  154
 16  ω   -173.00 -88.00   0.50    0.80    -- -102.00 -45.00  90.00  170
 17  ω   -109.00 -78.00   0.50    0.80    -- -102.00 -77.00  60.00   62
 18  ω   -173.00 -93.00   0.50    0.80    -- -102.00 -45.00 -30.00  160
 19  ω    -61.00 -30.00   0.50    0.80    -- -102.00  61.00 -90.00   62
 20  ω   -112.00 -44.00   0.50    0.80    -- -102.00 125.00-120.00  136
 21  ω   -162.00 -90.00   0.50    0.80    -- -102.00 -45.00  60.00  144
 22  ω    -64.00 -29.00   0.50    0.80    -- -102.00  61.00-120.00   70
 23  ω   -108.00 -46.00   0.50    0.80    -- -102.00 109.00  66.22  124
 24  ω     38.00 105.00   0.50    0.80    --  106.06 -94.00  90.00  134
 25  ω     40.00  92.00   0.50    0.80    --  106.06 -94.00-150.00  104
 26  ω     87.00 112.00   0.50    0.80    --  106.06-125.00-150.00   50
 27  ω     33.00  58.00   0.50    0.80    --  106.06 -61.00-180.00   50
 28  ω     62.00 110.00   0.50    0.80    --  106.06-125.00 -30.00   96
 29  ω     33.00 106.00   0.50    0.80    --  106.06 -94.00   0.00  146
 30  ω     38.00  73.00   0.50    0.80    --  106.06-125.00-150.00   70
 31  ω     43.00  69.00   0.50    0.80    --  106.06 -61.00  60.00   52
 32  ω     37.00  70.00   0.50    0.80    --  106.06 -61.00 -90.00   66
 33  ω     95.00 176.00   0.50    0.80    --  106.06  30.00 -90.00  162
 34  ω     37.00  63.00   0.50    0.80    --  106.06-125.00   0.00   52
 35  ω     75.00 112.00   0.50    0.80    --  106.06-125.00   0.00   74
 36  ω     36.00  98.00   0.50    0.80    --  106.06 -94.00 150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1226459000
_diffrn_orient_matrix_UB_12      0.0439844000
_diffrn_orient_matrix_UB_13      0.0431301000
_diffrn_orient_matrix_UB_21      -0.0288065000
_diffrn_orient_matrix_UB_22      -0.0597638000
_diffrn_orient_matrix_UB_23      0.0667156000
_diffrn_orient_matrix_UB_31      0.2013665000
_diffrn_orient_matrix_UB_32      -0.0477451000
_diffrn_orient_matrix_UB_33      -0.0173626000
_diffrn_oxdiff_digest_frames     
;
0195b51cc90cdebe894d927e27742dd73900085f760
;
_diffrn_oxdiff_digest_hkl        
;
01ade4b17d6ee10002c932b88f065c11cc0e2e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6521
_reflns_number_total             9291
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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         0.381
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         8787
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0735
_refine_ls_restrained_S_all      1.095
_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)+(0.1623P)²+0.1103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2495
_refine_ls_wR_factor_ref         0.2625
_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 O(H) groups
2. Rigid bond restraints
 C4, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O3, C1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C20(H20a,H20b), C22(H22a,H22b), C5(H5a,H5b), C3(H3a,H3b)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C6(H6), C30(H30), C31(H31), C19(H19), C15(H15), C14(H14),
 C27(H27), C28(H28)
3.c Idealised tetrahedral OH refined as rotating group:
 O7(H7), O2(H2), O3(H3), O5(H5)
;
_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 -0.5983(3) 0.89072(10) 0.12565(9) 0.1147(5) Uani 1 1 d . . . . .
F5 F 0.9352(3) 0.95021(9) 0.91942(9) 0.1177(6) Uani 1 1 d . . . . .
O1 O 0.5851(3) 0.53420(9) 0.07233(11) 0.1006(5) Uani 1 1 d . . . . .
F4 F 0.6369(3) 0.93661(9) 0.96688(10) 0.1235(6) Uani 1 1 d . . . . .
O8 O 1.3457(3) 0.65710(10) 0.91460(12) 0.1029(5) Uani 1 1 d . . . . .
F6 F 0.9130(4) 0.88840(10) 1.02485(8) 0.1215(6) Uani 1 1 d . . . . .
F1 F -0.6817(3) 0.82951(12) 0.22636(11) 0.1255(6) Uani 1 1 d . . . . .
O7 O 1.1233(3) 0.57290(9) 0.95363(11) 0.0994(5) Uani 1 1 d . . . . .
H7 H 1.227085 0.541922 0.954317 0.149 Uiso 1 1 calc GR . . . .
O2 O 0.3627(3) 0.45125(9) 0.11260(13) 0.1065(6) Uani 1 1 d . . . . .
H2 H 0.444779 0.422185 0.094030 0.160 Uiso 1 1 calc GR . . . .
O3 O -0.1662(4) 0.88414(15) 0.42944(10) 0.1159(7) Uani 1 1 d . U . . .
H3 H -0.136677 0.899318 0.465236 0.174 Uiso 1 1 calc GR . . . .
O5 O 0.2566(4) 0.94413(15) 0.49816(9) 0.1169(7) Uani 1 1 d . . . . .
H5 H 0.160069 0.962363 0.471708 0.175 Uiso 1 1 calc GR . . . .
F3 F -0.6883(3) 0.95298(12) 0.20855(13) 0.1378(7) Uani 1 1 d . . . . .
O4 O 0.0605(3) 0.95943(13) 0.37839(10) 0.1108(6) Uani 1 1 d . . . . .
O6 O 0.0303(4) 0.87010(16) 0.55188(10) 0.1247(7) Uani 1 1 d . . . . .
C21 C 0.8234(3) 0.82717(11) 0.93255(10) 0.0718(5) Uani 1 1 d . . . . .
C10 C -0.0061(4) 0.69881(11) 0.15772(10) 0.0772(5) Uani 1 1 d . . . . .
C8 C -0.2473(4) 0.81299(12) 0.19702(11) 0.0781(5) Uani 1 1 d . . . . .
C13 C 0.2657(3) 0.58112(11) 0.11929(11) 0.0770(5) Uani 1 1 d . . . . .
C16 C 0.4180(4) 0.51922(12) 0.09960(13) 0.0825(6) Uani 1 1 d . . . . .
C18 C 1.0128(3) 0.70303(11) 0.94830(11) 0.0751(5) Uani 1 1 d . . . . .
C11 C 0.1830(4) 0.71309(12) 0.12885(12) 0.0832(6) Uani 1 1 d . . . . .
H11 H 0.219337 0.762612 0.122086 0.100 Uiso 1 1 calc R . . . .
C9 C -0.1426(4) 0.75975(12) 0.17916(11) 0.0814(6) Uani 1 1 d . . . . .
C2 C -0.1861(3) 0.92350(13) 0.30799(11) 0.0794(5) Uani 1 1 d . . . . .
C24 C 0.7270(4) 0.84427(12) 0.86288(10) 0.0797(5) Uani 1 1 d . . . . .
C26 C 0.5340(4) 0.86614(13) 0.74136(10) 0.0807(6) Uani 1 1 d . . . . .
C17 C 1.1732(4) 0.64085(13) 0.93774(12) 0.0800(5) Uani 1 1 d . . . . .
C1 C -0.0877(4) 0.92190(15) 0.37718(13) 0.0887(6) Uani 1 1 d . U . . .
C4 C -0.3641(3) 0.87982(12) 0.21950(11) 0.0765(5) Uani 1 1 d . U . . .
C12 C 0.3195(4) 0.65497(12) 0.10980(12) 0.0824(6) Uani 1 1 d . . . . .
H12 H 0.447475 0.665252 0.090630 0.099 Uiso 1 1 calc R . . . .
C29 C 0.3132(4) 0.88909(14) 0.61737(11) 0.0834(6) Uani 1 1 d . . . . .
C25 C 0.6450(4) 0.85469(13) 0.80710(11) 0.0831(6) Uani 1 1 d . . . . .
C6 C -0.1423(4) 0.96675(13) 0.24793(12) 0.0794(5) Uani 1 1 d . . . . .
H6 H -0.045782 1.001506 0.243700 0.095 Uiso 1 1 calc R . . . .
C30 C 0.4902(4) 0.92250(15) 0.61944(11) 0.0869(6) Uani 1 1 d . . . . .
H30 H 0.536171 0.952705 0.578987 0.104 Uiso 1 1 calc R . . . .
C31 C 0.6018(4) 0.91152(14) 0.68169(11) 0.0848(6) Uani 1 1 d . . . . .
H31 H 0.721302 0.934641 0.683037 0.102 Uiso 1 1 calc R . . . .
C19 C 0.8306(3) 0.69410(12) 0.97794(11) 0.0777(5) Uani 1 1 d . . . . .
H19 H 0.784983 0.646699 0.993941 0.093 Uiso 1 1 calc R . . . .
C32 C 0.1917(4) 0.90142(16) 0.55138(12) 0.0928(7) Uani 1 1 d . . . . .
C20 C 0.7067(3) 0.76857(13) 0.98277(11) 0.0795(5) Uani 1 1 d . . . . .
H20A H 0.703557 0.778644 1.030689 0.095 Uiso 1 1 calc R . . . .
H20B H 0.566468 0.769620 0.967041 0.095 Uiso 1 1 calc R . . . .
C22 C 1.0477(4) 0.78548(12) 0.92902(13) 0.0834(6) Uani 1 1 d . . . . .
H22A H 1.106329 0.796598 0.881993 0.100 Uiso 1 1 calc R . . . .
H22B H 1.137373 0.799666 0.962594 0.100 Uiso 1 1 calc R . . . .
C5 C -0.2628(4) 0.95427(13) 0.18771(12) 0.0851(6) Uani 1 1 d . . . . .
H5A H -0.173910 0.946161 0.147852 0.102 Uiso 1 1 calc R . . . .
H5B H -0.366915 0.997309 0.172892 0.102 Uiso 1 1 calc R . . . .
C15 C -0.0616(4) 0.62493(14) 0.16516(15) 0.0939(7) Uani 1 1 d . . . . .
H15 H -0.190928 0.614925 0.183224 0.113 Uiso 1 1 calc R . . . .
C14 C 0.0742(4) 0.56636(13) 0.14588(15) 0.0909(6) Uani 1 1 d . . . . .
H14 H 0.036226 0.517188 0.150861 0.109 Uiso 1 1 calc R . . . .
C23 C 0.8269(4) 0.90156(14) 0.96109(12) 0.0902(7) Uani 1 1 d . . . . .
C3 C -0.3504(4) 0.87532(15) 0.29988(13) 0.0894(6) Uani 1 1 d . . . . .
H3A H -0.480444 0.895359 0.319013 0.107 Uiso 1 1 calc R . . . .
H3B H -0.313482 0.822921 0.323465 0.107 Uiso 1 1 calc R . . . .
C27 C 0.3574(5) 0.83203(18) 0.73869(13) 0.1026(8) Uani 1 1 d . . . . .
H27 H 0.312558 0.801048 0.778848 0.123 Uiso 1 1 calc R . . . .
C7 C -0.5829(4) 0.88832(17) 0.19488(17) 0.0997(7) Uani 1 1 d . U . . .
C28 C 0.2465(5) 0.84325(18) 0.67726(13) 0.1030(8) Uani 1 1 d . . . . .
H28 H 0.127094 0.820077 0.676007 0.124 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 C7 1.332(3) . ?
F5 C23 1.330(3) . ?
O1 C16 1.237(3) . ?
F4 C23 1.332(3) . ?
O8 C17 1.248(3) . ?
F6 C23 1.335(3) . ?
F1 C7 1.344(4) . ?
O7 H7 0.8200 . ?
O7 C17 1.278(3) . ?
O2 H2 0.8200 . ?
O2 C16 1.289(3) . ?
O3 H3 0.8200 . ?
O3 C1 1.243(3) . ?
O5 H5 0.8200 . ?
O5 C32 1.260(3) . ?
F3 C7 1.335(3) . ?
O4 C1 1.247(3) . ?
O6 C32 1.252(3) . ?
C21 C24 1.465(3) . ?
C21 C20 1.552(3) . ?
C21 C22 1.566(3) . ?
C21 C23 1.529(3) . ?
C10 C11 1.375(4) . ?
C10 C9 1.433(3) . ?
C10 C15 1.394(3) . ?
C8 C9 1.198(3) . ?
C8 C4 1.462(3) . ?
C13 C16 1.489(3) . ?
C13 C12 1.387(3) . ?
C13 C14 1.376(4) . ?
C18 C17 1.469(3) . ?
C18 C19 1.321(3) . ?
C18 C22 1.498(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(3) . ?
C2 C1 1.490(3) . ?
C2 C6 1.317(3) . ?
C2 C3 1.484(3) . ?
C24 C25 1.188(3) . ?
C26 C25 1.447(3) . ?
C26 C31 1.379(3) . ?
C26 C27 1.375(4) . ?
C4 C5 1.577(3) . ?
C4 C3 1.540(3) . ?
C4 C7 1.501(4) . ?
C12 H12 0.9300 . ?
C29 C30 1.370(4) . ?
C29 C32 1.486(3) . ?
C29 C28 1.383(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.483(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.392(3) . ?
C31 H31 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.487(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C27 H27 0.9300 . ?
C27 C28 1.376(4) . ?
C28 H28 0.9300 . ?

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
C17 O7 H7 109.5 . . ?
C16 O2 H2 109.5 . . ?
C1 O3 H3 109.5 . . ?
C32 O5 H5 109.5 . . ?
C24 C21 C20 109.79(19) . . ?
C24 C21 C22 111.17(16) . . ?
C24 C21 C23 109.43(16) . . ?
C20 C21 C22 104.20(15) . . ?
C23 C21 C20 112.04(17) . . ?
C23 C21 C22 110.1(2) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 C15 118.97(19) . . ?
C15 C10 C9 121.3(2) . . ?
C9 C8 C4 176.7(3) . . ?
C12 C13 C16 118.6(2) . . ?
C14 C13 C16 121.3(2) . . ?
C14 C13 C12 120.02(19) . . ?
O1 C16 O2 123.79(19) . . ?
O1 C16 C13 120.5(2) . . ?
O2 C16 C13 115.7(2) . . ?
C17 C18 C22 121.7(2) . . ?
C19 C18 C17 125.6(2) . . ?
C19 C18 C22 112.63(18) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C8 C9 C10 176.3(3) . . ?
C6 C2 C1 125.5(2) . . ?
C6 C2 C3 112.1(2) . . ?
C3 C2 C1 122.4(2) . . ?
C25 C24 C21 176.7(2) . . ?
C31 C26 C25 120.8(2) . . ?
C27 C26 C25 119.5(2) . . ?
C27 C26 C31 119.7(2) . . ?
O8 C17 O7 124.7(2) . . ?
O8 C17 C18 119.1(2) . . ?
O7 C17 C18 116.2(2) . . ?
O3 C1 O4 125.7(2) . . ?
O3 C1 C2 116.0(2) . . ?
O4 C1 C2 118.3(2) . . ?
C8 C4 C5 109.90(18) . . ?
C8 C4 C3 111.24(19) . . ?
C8 C4 C7 109.95(18) . . ?
C3 C4 C5 103.93(17) . . ?
C7 C4 C5 109.5(2) . . ?
C7 C4 C3 112.2(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C30 C29 C32 120.7(2) . . ?
C30 C29 C28 119.8(2) . . ?
C28 C29 C32 119.5(2) . . ?
C24 C25 C26 176.5(3) . . ?
C2 C6 H6 123.5 . . ?
C2 C6 C5 113.0(2) . . ?
C5 C6 H6 123.5 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.4(2) . . ?
C31 C30 H30 119.8 . . ?
C26 C31 C30 119.6(2) . . ?
C26 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C18 C19 H19 123.9 . . ?
C18 C19 C20 112.23(19) . . ?
C20 C19 H19 123.9 . . ?
O5 C32 C29 117.5(2) . . ?
O6 C32 O5 123.8(2) . . ?
O6 C32 C29 118.7(2) . . ?
C21 C20 H20A 111.2 . . ?
C21 C20 H20B 111.2 . . ?
C19 C20 C21 102.99(16) . . ?
C19 C20 H20A 111.2 . . ?
C19 C20 H20B 111.2 . . ?
H20A C20 H20B 109.1 . . ?
C21 C22 H22A 111.4 . . ?
C21 C22 H22B 111.4 . . ?
C18 C22 C21 101.78(19) . . ?
C18 C22 H22A 111.4 . . ?
C18 C22 H22B 111.4 . . ?
H22A C22 H22B 109.3 . . ?
C4 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
C6 C5 C4 102.67(18) . . ?
C6 C5 H5A 111.2 . . ?
C6 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.5(2) . . ?
C14 C15 H15 119.8 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
F5 C23 F4 107.8(2) . . ?
F5 C23 F6 106.9(2) . . ?
F5 C23 C21 111.76(18) . . ?
F4 C23 F6 107.66(19) . . ?
F4 C23 C21 111.1(2) . . ?
F6 C23 C21 111.32(18) . . ?
C2 C3 C4 103.91(19) . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C26 C27 H27 119.6 . . ?
C26 C27 C28 120.7(2) . . ?
C28 C27 H27 119.6 . . ?
F2 C7 F1 106.3(2) . . ?
F2 C7 F3 106.2(2) . . ?
F2 C7 C4 113.2(2) . . ?
F1 C7 C4 111.4(2) . . ?
F3 C7 F1 108.0(2) . . ?
F3 C7 C4 111.3(2) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 C29 119.8(3) . . ?
C27 C28 H28 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C11 C12 C13 0.5(4) . . . . ?
C10 C15 C14 C13 0.1(4) . . . . ?
C8 C4 C5 C6 -100.04(19) . . . . ?
C8 C4 C3 C2 98.0(2) . . . . ?
C8 C4 C7 F2 -54.3(3) . . . . ?
C8 C4 C7 F1 65.5(3) . . . . ?
C8 C4 C7 F3 -173.9(2) . . . . ?
C16 C13 C12 C11 -178.8(2) . . . . ?
C16 C13 C14 C15 178.5(2) . . . . ?
C18 C19 C20 C21 14.4(2) . . . . ?
C11 C10 C15 C14 2.0(4) . . . . ?
C9 C10 C11 C12 178.0(2) . . . . ?
C9 C10 C15 C14 -178.3(2) . . . . ?
C2 C6 C5 C4 -11.3(2) . . . . ?
C24 C21 C20 C19 96.04(19) . . . . ?
C24 C21 C22 C18 -94.7(2) . . . . ?
C24 C21 C23 F5 -60.8(3) . . . . ?
C24 C21 C23 F4 59.7(2) . . . . ?
C24 C21 C23 F6 179.7(2) . . . . ?
C26 C27 C28 C29 0.2(5) . . . . ?
C17 C18 C19 C20 178.1(2) . . . . ?
C17 C18 C22 C21 166.90(18) . . . . ?
C1 C2 C6 C5 178.7(2) . . . . ?
C1 C2 C3 C4 -165.9(2) . . . . ?
C12 C13 C16 O1 -3.3(3) . . . . ?
C12 C13 C16 O2 177.0(2) . . . . ?
C12 C13 C14 C15 -2.1(4) . . . . ?
C29 C30 C31 C26 0.6(4) . . . . ?
C25 C26 C31 C30 -179.0(2) . . . . ?
C25 C26 C27 C28 178.6(3) . . . . ?
C6 C2 C1 O3 171.8(2) . . . . ?
C6 C2 C1 O4 -6.3(4) . . . . ?
C6 C2 C3 C4 14.6(3) . . . . ?
C30 C29 C32 O5 -0.7(4) . . . . ?
C30 C29 C32 O6 -179.7(3) . . . . ?
C30 C29 C28 C27 0.6(4) . . . . ?
C31 C26 C27 C28 -0.6(4) . . . . ?
C19 C18 C17 O8 -173.8(2) . . . . ?
C19 C18 C17 O7 6.0(3) . . . . ?
C19 C18 C22 C21 -16.1(2) . . . . ?
C32 C29 C30 C31 179.1(2) . . . . ?
C32 C29 C28 C27 -179.5(3) . . . . ?
C20 C21 C22 C18 23.5(2) . . . . ?
C20 C21 C23 F5 177.16(19) . . . . ?
C20 C21 C23 F4 -62.3(2) . . . . ?
C20 C21 C23 F6 57.7(3) . . . . ?
C22 C21 C20 C19 -23.1(2) . . . . ?
C22 C21 C23 F5 61.7(2) . . . . ?
C22 C21 C23 F4 -177.80(17) . . . . ?
C22 C21 C23 F6 -57.8(3) . . . . ?
C22 C18 C17 O8 2.8(3) . . . . ?
C22 C18 C17 O7 -177.4(2) . . . . ?
C22 C18 C19 C20 1.3(3) . . . . ?
C5 C4 C3 C2 -20.2(2) . . . . ?
C5 C4 C7 F2 66.5(3) . . . . ?
C5 C4 C7 F1 -173.74(19) . . . . ?
C5 C4 C7 F3 -53.1(3) . . . . ?
C15 C10 C11 C12 -2.3(3) . . . . ?
C14 C13 C16 O1 176.2(2) . . . . ?
C14 C13 C16 O2 -3.6(3) . . . . ?
C14 C13 C12 C11 1.8(4) . . . . ?
C23 C21 C20 C19 -142.2(2) . . . . ?
C23 C21 C22 C18 143.85(17) . . . . ?
C3 C2 C1 O3 -7.6(3) . . . . ?
C3 C2 C1 O4 174.3(2) . . . . ?
C3 C2 C6 C5 -1.9(3) . . . . ?
C3 C4 C5 C6 19.1(2) . . . . ?
C3 C4 C7 F2 -178.7(2) . . . . ?
C3 C4 C7 F1 -58.9(3) . . . . ?
C3 C4 C7 F3 61.7(3) . . . . ?
C27 C26 C31 C30 0.2(4) . . . . ?
C7 C4 C5 C6 139.12(19) . . . . ?
C7 C4 C3 C2 -138.4(2) . . . . ?
C28 C29 C30 C31 -1.0(4) . . . . ?
C28 C29 C32 O5 179.4(3) . . . . ?
C28 C29 C32 O6 0.4(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.003 0.500 0.500 832.8 225.4 ?


_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 2.907
_oxdiff_exptl_absorpt_empirical_full_min 0.416
