# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_heat1_auto
_database_code_depnum_ccdc_archive 'CCDC 2415163'
loop_
_audit_author_name
_audit_author_address
'Hui Wang'
;Qingdao University of Science and Technology
China
;
_audit_update_record             
;
2025-01-07 deposited with the CCDC.	2025-07-28 downloaded from the CCDC.
;
_audit_creation_date             2024-10-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            heat
_chemical_name_systematic        M1'
_chemical_formula_moiety         'C66 H78 N3 O3, 3(B F4)'
_chemical_formula_sum            'C66 H78 B3 F12 N3 O3'
_chemical_formula_weight         1221.74
_chemical_melting_point          100
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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   27.228(3)
_cell_length_b                   27.228(3)
_cell_length_c                   15.692(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10075(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    1307
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.2410
_cell_measurement_theta_min      3.4060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            tan
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             3852
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8834
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        65.084
_diffrn_reflns_theta_max         65.084
_diffrn_reflns_theta_min         3.383
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  74.00   0.50    2.87    --   54.65  34.00 139.00  164
  2  ω    -65.00 -40.00   0.50    2.87    -- -102.00  58.00 120.00   50
  3  ω    -77.00 -51.00   0.50    2.87    -- -102.00 121.00  82.00   52
  4  ω     32.00  65.00   0.50    2.87    --  109.31 -58.00 -19.00   66
  5  ω     18.00  56.00   0.50    2.87    --  109.31 -89.00 -12.00   76
  6  ω    -87.00 -49.00   0.50    0.72    --    0.00-167.00 120.00   76
  7  ω    -10.00  26.00   0.50    2.87    --  -54.65  19.00-180.00   72
  8  ω     80.00 135.00   0.50    2.87    --   54.65 125.00  60.00  110
  9  ω     88.00 126.00   0.50    2.87    --   54.65 115.00  -4.00   76
 10  ω    -53.00 -23.00   0.50    2.87    -- -102.00  50.00 -60.00   60
 11  ω    -52.00 -26.00   0.50    2.87    -- -102.00  50.00-120.00   52
 12  ω     39.00  75.00   0.50    2.87    --  109.31 -63.00-120.00   72
 13  ω     32.00  63.00   0.50    2.87    --  109.31 -63.00 -30.00   62
 14  ω     27.00  53.00   0.50    2.87    --  109.31 -50.00   0.00   52
 15  ω     49.00  75.00   0.50    2.87    --  109.31 -63.00-180.00   52
 16  ω     33.00  62.00   0.50    2.87    --  109.31 -63.00  60.00   58
 17  ω     72.00 164.00   0.50    2.87    --  109.31  58.00 120.00  184
 18  ω     28.00  55.00   0.50    2.87    --  109.31 -50.00-180.00   54
 19  ω     71.00 105.00   0.50    2.87    --  109.31 -89.00 -12.00   68
;
_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      0.0484845000
_diffrn_orient_matrix_UB_12      0.0138235000
_diffrn_orient_matrix_UB_13      -0.0633381000
_diffrn_orient_matrix_UB_21      0.0431996000
_diffrn_orient_matrix_UB_22      0.0245575000
_diffrn_orient_matrix_UB_23      0.0732695000
_diffrn_orient_matrix_UB_31      -0.0067846000
_diffrn_orient_matrix_UB_32      -0.0590165000
_diffrn_orient_matrix_UB_33      0.0157218000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2091
_reflns_number_total             3763
_reflns_odcompleteness_completeness 98.25
_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 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.2382
_refine_ls_R_factor_gt           0.1821
_refine_ls_restrained_S_all      1.242
_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)+(0.0500P)²+70.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3212
_refine_ls_wR_factor_ref         0.3454
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C10 \\sim C19-C12 \\sim C22-C19 \\sim C20-C19 \\sim C21-C19 \\sim C15-C13
\\sim C18-C15 \\sim C16-C15
 \\sim C17-C15 \\sim C8-C5 \\sim C2-C1
 with sigma of 0.01
 F1-B1 \\sim F2-B1 \\sim F4-B1 \\sim F3-B1
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F2 \\sim B1 \\sim F1 \\sim F3 \\sim F4: within -2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within -2A
4.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C7(H7), C6(H6), C4(H4), C3(H3), C9(H9), C8(H8)
4.b Fitted hexagon refined as free rotating group:
 O1(C12,C11,C10,C14,C13), C2(C7,C6,C5,C4,C3)
4.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16(H16A,H16B,
 H16C), C22(H22A,H22B,H22C), C21(H21A,H21B,H21C)
;
_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
O1 O 0.68723(17) 0.5289(2) 0.6112(3) 0.1059(18) Uani 1 1 d G . . . .
C12 C 0.70166(19) 0.57730(19) 0.5635(3) 0.110(3) Uani 1 1 d DG . . . .
C11 C 0.6608(3) 0.5921(2) 0.5448(4) 0.119(3) Uani 1 1 d G . . . .
H11 H 0.670675 0.625144 0.512245 0.143 Uiso 1 1 calc R U . . .
C10 C 0.6055(2) 0.5585(3) 0.5738(4) 0.116(3) Uani 1 1 d DG . . . .
C14 C 0.59112(16) 0.5101(2) 0.6215(4) 0.103(3) Uani 1 1 d G . . . .
H14 H 0.553344 0.487135 0.641360 0.124 Uiso 1 1 calc R U . . .
C13 C 0.6320(2) 0.49532(18) 0.6402(3) 0.101(2) Uani 1 1 d DG . . . .
N1 N 0.3909(3) 0.7025(3) 0.5600(4) 0.098(2) Uani 1 1 d . . . . .
C1 C 0.3669(3) 0.6464(4) 0.5595(6) 0.098(2) Uani 1 1 d D . . . .
C2 C 0.4059(2) 0.6227(2) 0.5613(4) 0.099(2) Uani 1 1 d DG . . . .
C7 C 0.38537(19) 0.5661(2) 0.5820(4) 0.104(3) Uani 1 1 d G . . . .
H7 H 0.346285 0.542226 0.594561 0.125 Uiso 1 1 calc R U . . .
C6 C 0.4220(3) 0.5445(2) 0.5842(4) 0.119(3) Uani 1 1 d G . . . .
H6 H 0.407989 0.505807 0.598351 0.143 Uiso 1 1 calc R U . . .
C5 C 0.4792(3) 0.5795(3) 0.5658(4) 0.116(3) Uani 1 1 d DG . . . .
C4 C 0.49974(17) 0.6361(3) 0.5451(4) 0.135(4) Uani 1 1 d G . . . .
H4 H 0.538826 0.659999 0.532555 0.162 Uiso 1 1 calc R U . . .
C3 C 0.4631(2) 0.65773(19) 0.5429(4) 0.132(4) Uani 1 1 d G . . . .
H3 H 0.477122 0.696420 0.528765 0.158 Uiso 1 1 calc R U . . .
F2 F 0.6960(3) 0.7903(3) 0.6572(7) 0.248(4) Uani 1 1 d D U . . .
C15 C 0.6271(4) 0.4471(3) 0.6928(6) 0.117(3) Uani 1 1 d D . . . .
C19 C 0.7626(3) 0.6048(3) 0.5359(6) 0.117(3) Uani 1 1 d D . . . .
F1 F 0.6595(5) 0.7236(4) 0.5608(8) 0.276(5) Uani 1 1 d D U . . .
F3 F 0.6319(4) 0.7078(4) 0.6843(7) 0.275(5) Uani 1 1 d D U . . .
C9 C 0.5673(4) 0.5821(4) 0.5574(7) 0.139(4) Uani 1 1 d D . . . .
H9 H 0.581917 0.618458 0.531961 0.167 Uiso 1 1 calc R U . . .
C8 C 0.5175(4) 0.5547(4) 0.5768(7) 0.137(4) Uani 1 1 d D . . . .
H8 H 0.502611 0.517425 0.598875 0.164 Uiso 1 1 calc R U . . .
C20 C 0.7617(4) 0.5771(4) 0.4526(7) 0.148(4) Uani 1 1 d D . . . .
H20A H 0.744040 0.536074 0.460776 0.222 Uiso 1 1 calc R U . . .
H20B H 0.800541 0.592281 0.431813 0.222 Uiso 1 1 calc R U . . .
H20C H 0.739742 0.585006 0.410745 0.222 Uiso 1 1 calc R U . . .
C17 C 0.6366(6) 0.4651(5) 0.7844(7) 0.172(5) Uani 1 1 d D . . . .
H17A H 0.673218 0.500044 0.790243 0.258 Uiso 1 1 calc R U . . .
H17B H 0.636531 0.435123 0.819050 0.258 Uiso 1 1 calc R U . . .
H17C H 0.606217 0.471802 0.803682 0.258 Uiso 1 1 calc R U . . .
C18 C 0.6677(5) 0.4278(4) 0.6661(7) 0.161(5) Uani 1 1 d D . . . .
H18A H 0.659312 0.413505 0.607481 0.241 Uiso 1 1 calc R U . . .
H18B H 0.663682 0.397438 0.704200 0.241 Uiso 1 1 calc R U . . .
H18C H 0.706636 0.459714 0.669232 0.241 Uiso 1 1 calc R U . . .
F4 F 0.7124(4) 0.7239(4) 0.6574(9) 0.295(5) Uani 1 1 d D U . . .
C16 C 0.5679(4) 0.3965(4) 0.6846(8) 0.174(5) Uani 1 1 d D . . . .
H16A H 0.540083 0.407230 0.703053 0.261 Uiso 1 1 calc R U . . .
H16B H 0.564498 0.365515 0.720401 0.261 Uiso 1 1 calc R U . . .
H16C H 0.560651 0.384126 0.625019 0.261 Uiso 1 1 calc R U . . .
C22 C 0.7843(5) 0.6673(4) 0.5245(9) 0.187(6) Uani 1 1 d D . . . .
H22A H 0.760925 0.672760 0.482232 0.281 Uiso 1 1 calc R U . . .
H22B H 0.823738 0.686071 0.504724 0.281 Uiso 1 1 calc R U . . .
H22C H 0.782381 0.683833 0.578984 0.281 Uiso 1 1 calc R U . . .
C21 C 0.7971(4) 0.5936(5) 0.6004(8) 0.179(5) Uani 1 1 d D . . . .
H21A H 0.794069 0.607998 0.656222 0.269 Uiso 1 1 calc R U . . .
H21B H 0.836877 0.612724 0.582565 0.269 Uiso 1 1 calc R U . . .
H21C H 0.782542 0.552642 0.604299 0.269 Uiso 1 1 calc R U . . .
B1 B 0.6758(5) 0.7383(4) 0.6379(8) 0.231(5) Uani 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.3900 . ?
O1 C13 1.3900 . ?
C12 C11 1.3900 . ?
C12 C19 1.504(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.3900 . ?
C10 C14 1.3900 . ?
C10 C9 1.495(6) . ?
C14 H14 0.9500 . ?
C14 C13 1.3900 . ?
C13 C15 1.498(6) . ?
N1 C1 1.330(8) 2_665 ?
N1 C1 1.327(8) . ?
C1 C2 1.493(6) . ?
C2 C7 1.3900 . ?
C2 C3 1.3900 . ?
C7 H7 0.9500 . ?
C7 C6 1.3900 . ?
C6 H6 0.9500 . ?
C6 C5 1.3900 . ?
C5 C4 1.3900 . ?
C5 C8 1.509(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 H3 0.9500 . ?
F2 B1 1.271(7) . ?
C15 C17 1.498(7) . ?
C15 C18 1.504(6) . ?
C15 C16 1.514(7) . ?
C19 C20 1.502(7) . ?
C19 C22 1.509(7) . ?
C19 C21 1.511(7) . ?
F1 B1 1.282(7) . ?
F3 B1 1.287(8) . ?
C9 H9 0.9500 . ?
C9 C8 1.215(12) . ?
C8 H8 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
F4 B1 1.277(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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 O1 C13 120.0 . . ?
O1 C12 C19 110.2(5) . . ?
C11 C12 O1 120.0 . . ?
C11 C12 C19 129.7(5) . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 C9 114.7(6) . . ?
C14 C10 C11 120.0 . . ?
C14 C10 C9 125.0(6) . . ?
C10 C14 H14 120.0 . . ?
C10 C14 C13 120.0 . . ?
C13 C14 H14 120.0 . . ?
O1 C13 C15 110.5(5) . . ?
C14 C13 O1 120.0 . . ?
C14 C13 C15 129.5(5) . . ?
C1 N1 C1 113.3(7) . 2_665 ?
N1 C1 N1 126.6(7) . 3_565 ?
N1 C1 C2 116.6(7) . . ?
N1 C1 C2 116.7(7) 3_565 . ?
C7 C2 C1 120.3(5) . . ?
C7 C2 C3 120.0 . . ?
C3 C2 C1 119.7(5) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C5 C8 117.2(6) . . ?
C4 C5 C6 120.0 . . ?
C4 C5 C8 122.5(6) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C13 C15 C18 113.2(7) . . ?
C13 C15 C16 109.7(7) . . ?
C17 C15 C13 108.5(7) . . ?
C17 C15 C18 110.1(8) . . ?
C17 C15 C16 108.1(9) . . ?
C18 C15 C16 107.0(8) . . ?
C12 C19 C22 107.9(7) . . ?
C12 C19 C21 110.3(7) . . ?
C20 C19 C12 105.2(6) . . ?
C20 C19 C22 111.2(9) . . ?
C20 C19 C21 109.8(9) . . ?
C22 C19 C21 112.1(9) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.7(9) . . ?
C8 C9 H9 120.2 . . ?
C5 C8 H8 119.8 . . ?
C9 C8 C5 120.3(9) . . ?
C9 C8 H8 119.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F2 B1 F1 117.5(11) . . ?
F2 B1 F3 109.2(10) . . ?
F2 B1 F4 108.4(9) . . ?
F1 B1 F3 105.4(10) . . ?
F4 B1 F1 109.4(11) . . ?
F4 B1 F3 106.3(10) . . ?

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
O1 C12 C11 C10 0.0 . . . . ?
O1 C12 C19 C20 88.5(7) . . . . ?
O1 C12 C19 C22 -152.7(7) . . . . ?
O1 C12 C19 C21 -29.9(9) . . . . ?
O1 C13 C15 C17 92.2(7) . . . . ?
O1 C13 C15 C18 -30.4(9) . . . . ?
O1 C13 C15 C16 -149.9(7) . . . . ?
C12 O1 C13 C14 0.0 . . . . ?
C12 O1 C13 C15 -177.7(6) . . . . ?
C12 C11 C10 C14 0.0 . . . . ?
C12 C11 C10 C9 173.9(6) . . . . ?
C11 C12 C19 C20 -88.2(8) . . . . ?
C11 C12 C19 C22 30.6(11) . . . . ?
C11 C12 C19 C21 153.3(7) . . . . ?
C11 C10 C14 C13 0.0 . . . . ?
C11 C10 C9 C8 176.5(9) . . . . ?
C10 C14 C13 O1 0.0 . . . . ?
C10 C14 C13 C15 177.2(7) . . . . ?
C10 C9 C8 C5 176.1(7) . . . . ?
C14 C10 C9 C8 -9.9(14) . . . . ?
C14 C13 C15 C17 -85.2(9) . . . . ?
C14 C13 C15 C18 152.2(7) . . . . ?
C14 C13 C15 C16 32.7(10) . . . . ?
C13 O1 C12 C11 0.0 . . . . ?
C13 O1 C12 C19 -177.1(5) . . . . ?
N1 C1 C2 C7 -14.1(10) 3_565 . . . ?
N1 C1 C2 C7 164.1(6) . . . . ?
N1 C1 C2 C3 166.4(6) 3_565 . . . ?
N1 C1 C2 C3 -15.4(10) . . . . ?
C1 N1 C1 N1 -1.1(18) 2_665 . . 3_565 ?
C1 N1 C1 C2 -179.1(4) 2_665 . . . ?
C1 C2 C7 C6 -179.5(6) . . . . ?
C1 C2 C3 C4 179.5(6) . . . . ?
C2 C7 C6 C5 0.0 . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C7 C6 C5 C4 0.0 . . . . ?
C7 C6 C5 C8 174.9(7) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C5 C8 C9 176.1(9) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C5 C8 C9 -9.1(14) . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C19 C12 C11 C10 176.5(7) . . . . ?
C9 C10 C14 C13 -173.2(7) . . . . ?
C8 C5 C4 C3 -174.6(7) . . . . ?

_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 0.000 0.000 0.500 23.6 0.0 ?
2 0.038 0.279 0.425 31.2 9.3 ?
3 0.054 0.425 0.092 31.2 9.3 ?
4 -0.091 0.296 0.759 31.2 9.3 ?
5 -0.054 0.575 0.908 31.2 9.2 ?
6 0.091 0.704 0.241 31.2 9.2 ?
7 -0.038 0.721 0.575 31.2 9.2 ?
8 0.242 0.962 0.425 31.2 9.3 ?
9 0.279 0.242 0.575 31.2 9.2 ?
10 0.296 0.387 0.241 31.2 9.2 ?
11 0.333 0.667 0.167 23.6 0.0 ?
12 0.371 0.946 0.092 31.2 9.3 ?
13 0.387 0.091 0.759 31.2 9.3 ?
14 0.425 0.371 0.908 31.2 9.2 ?
15 0.575 0.629 0.092 31.2 9.3 ?
16 0.629 0.054 0.908 31.2 9.2 ?
17 0.613 0.909 0.241 31.2 9.2 ?
18 0.667 0.333 0.833 23.6 0.0 ?
19 0.704 0.613 0.759 31.2 9.3 ?
20 0.721 0.758 0.425 31.2 9.3 ?
21 0.758 0.038 0.575 31.2 9.2 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

# end Validation Reply Form
_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 2.759
_oxdiff_exptl_absorpt_empirical_full_min 0.254
# start Validation Reply Form
_vrf_PLAT082_heat1_auto          
;
PROBLEM: High R1 Value ..................................       0.18 Report
RESPONSE: Due to the weak diffraction at high angles
;
_vrf_PLAT340_heat1_auto          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01164 Ang.  
RESPONSE: Due to the weak diffraction at high angles
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetic acid and formic acid (3:1 by volume)'
