# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_v088
_audit_block_doi                 10.5517/ccdc.csd.cc2gxmpq
_database_code_depnum_ccdc_archive 'CCDC 2291634'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/cssc.202401057 2024
loop_
_audit_author_name
_audit_author_address
'Joshua Barham'
;University of Regensburg
Germany
;
_audit_update_record             
;
2023-08-29 deposited with the CCDC.	2025-02-17 downloaded from the CCDC.
;
_audit_creation_date             2022-08-16
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
Shahboz.Yakubov@chemie.uni-regensburg.de
?
Birgit.Hischa@chemie.uni-regensburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H15 Cl N2, 2(B F4)'
_chemical_formula_sum            'C7 H15 B2 Cl F8 N2'
_chemical_formula_weight         336.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H15 B2 Cl F8 N2'
_chemical_oxdiff_usercomment     'Yakubov_Barham_SYSFH new'
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'
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.1167(2)
_cell_length_b                   12.7140(2)
_cell_length_c                   15.6393(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2608.10(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13763
_cell_measurement_temperature    143.01(10)
_cell_measurement_theta_max      74.6400
_cell_measurement_theta_min      5.5430
_shelx_estimated_absorpt_T_max   0.819
_shelx_estimated_absorpt_T_min   0.455
_exptl_absorpt_coefficient_mu    3.463
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.713
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -8 -2 0.0459
1 6 7 0.0140
8 2 0 0.1263
0 -3 -10 0.0360
-1 2 -10 0.0253
-8 0 -3 0.1301
-3 7 -5 0.0401
2 -7 5 0.0314
-1 7 5 0.0228
-9 0 0 0.1356
0 1 10 0.0326

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.5724 -8.0955 -1.8392 -0.2063 -0.8698 -0.4483
0.9347 5.5134 7.4604 -0.4244 0.7765 0.4657
8.3140 1.8153 -0.0969 0.1067 -0.2055 0.9728
-0.3187 -2.6024 -9.6168 0.7561 -0.5782 -0.3065
-1.1061 1.5096 -9.8832 0.9685 -0.1265 -0.2145
-8.0601 -0.4157 -3.2335 0.2618 0.2253 -0.9384
-2.7559 6.6659 -4.9916 0.7573 0.6475 -0.0847
2.4924 -6.7850 4.9461 -0.7591 -0.6490 0.0504
-0.9102 7.3357 4.5142 -0.0751 0.9512 0.2992
-8.5143 0.2286 0.3373 -0.0348 0.4336 -0.9004
-0.3876 0.6395 10.1037 -0.8922 0.4254 0.1520

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30229
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.507
_diffrn_reflns_theta_min         5.611
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      143.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     85.00 111.00   0.50    0.30    --   82.00  73.00 -64.05   52
  2  ω     88.00 113.00   0.50    0.30    --   82.00  66.00 -96.71   50
  3  ω     59.00  96.00   0.50    0.30    --   52.00  60.00-122.82   74
  4  ω     77.00 114.00   0.50    0.30    --   82.00  27.00-176.23   74
  5  ω     54.00  89.00   0.50    0.30    --   48.00  68.00 -62.30   70
  6  ω     94.00 128.00   0.50    0.30    --   82.00  47.00 116.28   68
  7  ω     63.00 110.00   0.50    0.30    --   60.79  31.00 173.00   94
  8  ω     81.00 128.00   0.50    0.30    --   78.43  31.00 173.00   94
  9  ω    102.00 128.00   0.50    0.30    --   82.00  10.00  51.85   52
 10  ω     65.00  95.00   0.50    0.30    --   82.00  23.00  51.53   60
 11  ω     52.00  81.00   0.50    0.30    --   82.00  10.00  51.85   58
 12  ω     51.00  81.00   0.50    0.30    --   82.00  16.00  21.39   60
 13  ω     72.00 131.00   0.50    0.30    --   82.00  22.00 -88.25  118
 14  ω     49.00 114.00   0.50    0.30    --   82.00  -3.00 -25.54  130
 15  ω     85.00 110.00   0.50    0.30    --   82.00  83.00-130.46   50
 16  ω     11.00  41.00   0.50    0.30    --   60.79 -31.00  13.00   60
 17  ω     50.00  76.00   0.50    0.30    --   82.00-133.00  28.66   52
 18  ω     46.00  72.00   0.50    0.30    --   82.00-157.00  16.44   52
 19  ω     48.00 114.00   0.50    0.30    --   82.00-128.00 -25.07  132
 20  ω     77.00 103.00   0.50    0.30    --   82.00-127.00 -70.62   52
 21  ω     49.00  74.00   0.50    0.30    --   82.00-127.00 -70.62   50
 22  ω     36.00  63.00   0.50    0.30    --   82.00-125.00-154.52   54
 23  ω     21.00  72.00   0.50    0.30    --   60.79 -95.00-168.00  102
 24  ω     39.00  89.00   0.50    0.30    --   78.43 -95.00-168.00  100
 25  ω     82.00 109.00   0.50    0.30    --   82.00-125.00-154.52   54
 26  ω     55.00  81.00   0.50    0.30    --   82.00 -81.00-107.18   52
 27  ω     15.00  86.00   0.50    0.30    --   60.79-114.00 -65.00  142
 28  ω     33.00 104.00   0.50    0.30    --   78.43-114.00 -65.00  142
 29  ω     43.00  68.00   0.50    0.30    --   82.00 -92.00 -23.51   50
 30  ω   -101.00 -30.00   0.50    0.30    --  -75.76 114.00  24.00  142
 31  ω    -74.00 -46.00   0.50    0.30    --  -80.00  68.00 -15.41   56
 32  ω    -67.00 -41.00   0.50    0.30    --  -80.00  62.00  29.32   52
 33  ω   -125.00 -78.00   0.50    0.30    --  -75.76 -31.00  13.00   94
 34  ω   -124.00 -88.00   0.50    0.30    --  -80.00 -57.00 -74.38   72
 35  ω   -110.00 -74.00   0.50    0.30    --  -72.00 -75.00 -79.12   72
 36  ω   -118.00 -92.00   0.50    0.30    --  -80.00 -66.00  67.94   52
 37  ω   -117.00 -81.00   0.50    0.30    --  -80.00 -77.00 119.96   72
 38  ω   -117.00 -79.00   0.50    0.30    --  -80.00 -83.00 150.44   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0017117000
_diffrn_orient_matrix_UB_12      0.0460649000
_diffrn_orient_matrix_UB_13      -0.0911504000
_diffrn_orient_matrix_UB_21      -0.0468263000
_diffrn_orient_matrix_UB_22      0.1030750000
_diffrn_orient_matrix_UB_23      0.0337800000
_diffrn_orient_matrix_UB_31      0.1075846000
_diffrn_orient_matrix_UB_32      0.0440455000
_diffrn_orient_matrix_UB_33      0.0163879000
_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                2362
_reflns_number_total             2683
_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 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0654
_refine_ls_restrained_S_all      1.053
_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)+(0.0762P)²+6.0474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1740
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F2A) = Uanis(F2) = Uanis(F3B) = Uanis(F1A) = Uanis(F1) = Uanis(F4B) =
Uanis(F2B) = Uanis(F3) = Uanis(F1B) = Uanis(F4A) = Uanis(F4) = Uanis(F3A)
3. Others
 1*[Sof(F2)+Sof(F3)+Sof(F1)+Sof(F4)]+1*[Sof(F1A)+Sof(F2A)+Sof(F4A)+Sof(F3A)]+1*
 [Sof(F4B)+Sof(F1B)+Sof(F3B)+Sof(F2B)]=1 with esd of 0.001
 Sof(F2)=Sof(F3)=Sof(F1)=Sof(F4)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F4A)=Sof(F3A)=FVAR(2)
 Sof(F4B)=Sof(F1B)=Sof(F3B)=Sof(F2B)=FVAR(3)
4.a Ternary CH refined with riding coordinates:
 N1(H1)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B),
 C2(H2A,H2B)
;
_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 0.60884(8) 0.08824(7) 0.53058(7) 0.0546(3) Uani 1 1 d . . . . .
F5 F 0.65388(14) 0.52423(14) 0.85409(11) 0.0337(4) Uani 1 1 d . . . . .
F6 F 0.80025(14) 0.52571(15) 0.77874(11) 0.0360(4) Uani 1 1 d . . . . .
F7 F 0.80662(16) 0.51277(15) 0.92335(11) 0.0409(5) Uani 1 1 d . . . . .
F8 F 0.75787(18) 0.66689(14) 0.86205(13) 0.0453(5) Uani 1 1 d . . . . .
N1 N 0.62341(19) 0.42389(18) 0.69586(15) 0.0270(5) Uani 1 1 d . . . . .
H1 H 0.649457 0.486854 0.727338 0.032 Uiso 1 1 calc R U . . .
N2 N 0.55845(18) 0.26508(18) 0.61674(14) 0.0248(5) Uani 1 1 d . . . . .
C1 C 0.6669(3) 0.4236(2) 0.60751(19) 0.0331(7) Uani 1 1 d . . . . .
H1A H 0.742253 0.420901 0.610387 0.040 Uiso 1 1 calc R U . . .
H1B H 0.647050 0.488876 0.577276 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4705(3) 0.3330(3) 0.6450(2) 0.0382(7) Uani 1 1 d . . . . .
H3A H 0.424961 0.292162 0.682984 0.046 Uiso 1 1 calc R U . . .
H3B H 0.430620 0.355615 0.594476 0.046 Uiso 1 1 calc R U . . .
C6 C 0.6171(3) 0.2308(2) 0.69472(19) 0.0328(7) Uani 1 1 d . . . . .
H6A H 0.675286 0.186003 0.677330 0.039 Uiso 1 1 calc R U . . .
H6B H 0.572355 0.188920 0.732654 0.039 Uiso 1 1 calc R U . . .
C4 C 0.5105(3) 0.4288(3) 0.6922(2) 0.0395(7) Uani 1 1 d . . . . .
H4A H 0.488891 0.493662 0.662158 0.047 Uiso 1 1 calc R U . . .
H4B H 0.482173 0.430558 0.750828 0.047 Uiso 1 1 calc R U . . .
C5 C 0.6560(3) 0.3265(2) 0.7422(2) 0.0381(8) Uani 1 1 d . . . . .
H5A H 0.628201 0.327102 0.801065 0.046 Uiso 1 1 calc R U . . .
H5B H 0.731264 0.324029 0.745873 0.046 Uiso 1 1 calc R U . . .
C7 C 0.5138(3) 0.1715(2) 0.5710(2) 0.0356(7) Uani 1 1 d . . . . .
H7A H 0.470321 0.196248 0.523360 0.043 Uiso 1 1 calc R U . . .
H7B H 0.470146 0.131467 0.611157 0.043 Uiso 1 1 calc R U . . .
C2 C 0.6270(3) 0.3285(2) 0.55919(19) 0.0363(7) Uani 1 1 d . . . . .
H2A H 0.588504 0.351833 0.508147 0.044 Uiso 1 1 calc R U . . .
H2B H 0.684808 0.284500 0.539783 0.044 Uiso 1 1 calc R U . . .
B1 B 0.7555(3) 0.5588(3) 0.8556(2) 0.0277(7) Uani 1 1 d . . . . .
B2 B 0.5919(3) 0.7098(3) 0.6284(2) 0.0306(7) Uani 1 1 d . . . . .
F2 F 0.6277(4) 0.6555(5) 0.6988(4) 0.0447(5) Uani 0.567(4) 1 d . . P A 1
F3 F 0.6030(4) 0.8163(3) 0.6526(3) 0.0447(5) Uani 0.567(4) 1 d . . P A 1
F1 F 0.6462(4) 0.6884(4) 0.5563(3) 0.0447(5) Uani 0.567(4) 1 d . . P A 1
F4 F 0.4920(3) 0.6861(4) 0.6195(3) 0.0447(5) Uani 0.567(4) 1 d . . P A 1
F1A F 0.6073(9) 0.6570(8) 0.5494(6) 0.0447(5) Uani 0.226(4) 1 d . . P A 2
F2A F 0.5972(9) 0.6459(11) 0.7033(8) 0.0447(5) Uani 0.226(4) 1 d . . P A 2
F4A F 0.4864(8) 0.7400(9) 0.6235(6) 0.0447(5) Uani 0.226(4) 1 d . . P A 2
F3A F 0.6299(9) 0.8092(9) 0.6268(7) 0.0447(5) Uani 0.226(4) 1 d . . P A 2
F4B F 0.5193(8) 0.6470(8) 0.5866(7) 0.0447(5) Uani 0.206(4) 1 d . . P A 3
F1B F 0.6744(9) 0.7220(9) 0.5721(7) 0.0447(5) Uani 0.206(4) 1 d . . P A 3
F3B F 0.5550(10) 0.8060(9) 0.6405(7) 0.0447(5) Uani 0.206(4) 1 d . . P A 3
F2B F 0.6513(10) 0.6480(12) 0.6837(9) 0.0447(5) Uani 0.206(4) 1 d . . P A 3


_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 C7 1.753(4) . ?
F5 B1 1.404(4) . ?
F6 B1 1.402(4) . ?
F7 B1 1.384(4) . ?
F8 B1 1.378(4) . ?
N1 H1 1.0000 . ?
N1 C1 1.495(4) . ?
N1 C4 1.484(4) . ?
N1 C5 1.497(4) . ?
N2 C3 1.507(4) . ?
N2 C6 1.506(3) . ?
N2 C7 1.507(4) . ?
N2 C2 1.506(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.519(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.518(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.514(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
B2 F2 1.382(7) . ?
B2 F3 1.414(6) . ?
B2 F1 1.361(5) . ?
B2 F4 1.351(5) . ?
B2 F1A 1.421(10) . ?
B2 F2A 1.427(14) . ?
B2 F4A 1.438(11) . ?
B2 F3A 1.359(12) . ?
B2 F4B 1.404(11) . ?
B2 F1B 1.403(12) . ?
B2 F3B 1.330(12) . ?
B2 F2B 1.404(16) . ?

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 N1 H1 109.1 . . ?
C1 N1 C5 109.7(2) . . ?
C4 N1 H1 109.1 . . ?
C4 N1 C1 110.2(2) . . ?
C4 N1 C5 109.8(3) . . ?
C5 N1 H1 109.1 . . ?
C6 N2 C3 108.6(2) . . ?
C6 N2 C7 110.7(2) . . ?
C7 N2 C3 107.1(2) . . ?
C2 N2 C3 109.0(2) . . ?
C2 N2 C6 109.5(2) . . ?
C2 N2 C7 111.8(2) . . ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
N1 C1 C2 109.3(2) . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
N2 C3 H3A 109.7 . . ?
N2 C3 H3B 109.7 . . ?
N2 C3 C4 109.8(3) . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
N2 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
N2 C6 C5 109.7(2) . . ?
H6A C6 H6B 108.2 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
N1 C4 C3 109.3(3) . . ?
N1 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C6 109.4(2) . . ?
N1 C5 H5A 109.8 . . ?
N1 C5 H5B 109.8 . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
Cl1 C7 H7A 109.3 . . ?
Cl1 C7 H7B 109.3 . . ?
N2 C7 Cl1 111.8(2) . . ?
N2 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
N2 C2 C1 109.5(2) . . ?
N2 C2 H2A 109.8 . . ?
N2 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
F6 B1 F5 106.8(2) . . ?
F7 B1 F5 109.9(2) . . ?
F7 B1 F6 109.1(3) . . ?
F8 B1 F5 109.6(3) . . ?
F8 B1 F6 110.6(3) . . ?
F8 B1 F7 110.8(2) . . ?
F2 B2 F3 103.3(4) . . ?
F1 B2 F2 112.5(4) . . ?
F1 B2 F3 111.0(4) . . ?
F4 B2 F2 107.5(4) . . ?
F4 B2 F3 109.9(4) . . ?
F4 B2 F1 112.2(4) . . ?
F1A B2 F2A 116.0(7) . . ?
F1A B2 F4A 102.5(6) . . ?
F2A B2 F4A 104.0(6) . . ?
F3A B2 F1A 111.8(6) . . ?
F3A B2 F2A 121.8(8) . . ?
F3A B2 F4A 96.0(7) . . ?
F4B B2 F2B 110.2(8) . . ?
F1B B2 F4B 107.1(7) . . ?
F1B B2 F2B 91.2(7) . . ?
F3B B2 F4B 110.1(7) . . ?
F3B B2 F1B 105.5(7) . . ?
F3B B2 F2B 128.9(9) . . ?

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
N1 C1 C2 N2 -1.0(4) . . . . ?
N2 C3 C4 N1 -0.5(4) . . . . ?
N2 C6 C5 N1 -0.1(4) . . . . ?
C1 N1 C4 C3 60.7(3) . . . . ?
C1 N1 C5 C6 -60.4(3) . . . . ?
C3 N2 C6 C5 -59.4(3) . . . . ?
C3 N2 C7 Cl1 177.5(2) . . . . ?
C3 N2 C2 C1 59.9(3) . . . . ?
C6 N2 C3 C4 60.0(3) . . . . ?
C6 N2 C7 Cl1 -64.2(3) . . . . ?
C6 N2 C2 C1 -58.8(3) . . . . ?
C4 N1 C1 C2 -59.9(3) . . . . ?
C4 N1 C5 C6 60.8(3) . . . . ?
C5 N1 C1 C2 61.0(3) . . . . ?
C5 N1 C4 C3 -60.2(3) . . . . ?
C7 N2 C3 C4 179.7(3) . . . . ?
C7 N2 C6 C5 -176.7(3) . . . . ?
C7 N2 C2 C1 178.1(3) . . . . ?
C2 N2 C3 C4 -59.2(3) . . . . ?
C2 N2 C6 C5 59.5(3) . . . . ?
C2 N2 C7 Cl1 58.2(3) . . . . ?

_olex2_date_sample_submission    2022-08-11
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id 'SYSFFH new'
_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 2.389
_oxdiff_exptl_absorpt_empirical_full_min 0.352
####################################################################### 
# 
# 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_v103
_database_code_depnum_ccdc_archive 'CCDC 2381200'
loop_
_audit_author_name
_audit_author_address
'Joshua Barham'
;University of Regensburg
Germany
;
_audit_update_record             
;
2024-09-01 deposited with the CCDC.	2025-02-17 downloaded from the CCDC.
;
_audit_creation_date             2022-10-27
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
loop_
_audit_author_email
Shahboz.Yakubov@chemie.uni-regensburg.de
?
xray@ur.de
_chemical_formula_moiety         'C16 H25.054 F0.946 O2'
_chemical_formula_sum            'C16 H25.054 F0.946 O2'
_chemical_formula_weight         267.385
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   5.9658(1)
_cell_length_b                   13.5775(1)
_cell_length_c                   17.6402(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1428.87(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16192
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      74.4660
_cell_measurement_theta_min      4.0940
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       prism
_exptl_crystal_F_000             584.173
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -8 4 0.0371
2 -7 4 0.0416
3 -5 4 0.0386
3 -4 -7 0.0553
0 -3 -11 0.0622
-1 -3 11 0.0569
3 -3 4 0.0432
3 0 -8 0.0532
0 0 -11 0.0620
4 0 5 0.0470
1 2 11 0.0692
3 4 -6 0.0436
-1 7 5 0.0619
-2 8 3 0.0611
0 8 -5 0.0457
-4 -1 0 0.0383
2 7 -4 0.0332
3 6 0 0.0401

_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.083
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26733
_diffrn_reflns_point_group_measured_fraction_full 0.9996
_diffrn_reflns_point_group_measured_fraction_max 0.9902
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         75.01
_diffrn_reflns_theta_min         4.11
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  68.00   0.50    0.70    --   63.22 -95.00   0.00   56
  2  ω     58.00  84.00   0.50    0.70    --   63.22   0.00 -30.00   52
  3  ω     26.00  70.00   0.50    0.70    --   63.22 -95.00-180.00   88
  4  ω     29.00  54.00   0.50    0.70    --   63.22   0.00 -30.00   50
  5  ω    -70.00 -27.00   0.50    0.70    --  -63.82 125.00  60.00   86
  6  ω   -107.00 -52.00   0.50    0.70    --  -63.82 -15.00 -30.00  110
  7  ω    -80.00 -50.00   0.50    0.70    --  -63.82 -15.00 -90.00   60
  8  ω   -100.00 -71.00   0.50    0.70    --  -73.72 125.00 150.00   58
  9  ω    -66.00 -34.00   0.50    0.70    --  -73.72 125.00 150.00   64
 10  ω   -108.00 -67.00   0.50    0.70    --  -73.72   0.00 -90.00   82
 11  ω   -116.00 -45.00   0.50    0.70    --  -73.72 -15.00-150.00  142
 12  ω    -61.00 -34.00   0.50    0.70    --  -73.72 125.00 120.00   54
 13  ω   -100.00 -40.00   0.50    0.70    --  -73.72 125.00-120.00  120
 14  ω   -100.00 -38.00   0.50    0.70    --  -73.72 125.00   0.00  124
 15  ω   -100.00 -74.00   0.50    0.70    --  -73.72 125.00 120.00   52
 16  ω     40.00  74.00   0.50    0.70    --   75.80 -95.00 -30.00   68
 17  ω     49.00  75.00   0.50    0.70    --   75.87 -95.00-120.00   52
 18  ω   -116.00 -83.00   0.50    0.70    --  -76.77-125.00  60.00   66
 19  ω    -82.00 -36.00   0.50    0.70    --  -78.25 135.00 -80.58   92
 20  ω    -69.00 -43.00   0.50    0.70    --  -78.25  97.00  82.43   52
 21  ω   -106.00 -68.00   0.50    0.70    --  -78.25-133.00-154.71   76
 22  ω    -92.00 -66.00   0.50    0.70    --  -78.25 121.00 -95.75   52
 23  ω    -85.00 -59.00   0.50    0.70    --  -78.25 117.00 -50.10   52
 24  ω   -107.00 -82.00   0.50    0.70    --  -78.25 127.00-162.13   50
 25  ω    -83.00 -58.00   0.50    0.70    --  -78.25  90.00 139.12   50
 26  ω   -110.00 -83.00   0.50    0.70    --  -78.25 135.00 156.00   54
 27  ω   -113.00 -79.00   0.50    0.70    --  -78.25 -91.00 -96.80   68
 28  ω   -112.00 -87.00   0.50    0.70    --  -78.25 135.00 -80.58   50
 29  ω    -93.00 -58.00   0.50    0.70    --  -78.25 121.00 153.35   70
 30  ω   -114.00 -82.00   0.50    0.70    --  -78.25 138.00  10.43   64
 31  ω   -108.00 -82.00   0.50    0.70    --  -78.25 -87.00  50.42   52
 32  ω    -71.00 -45.00   0.50    0.70    --  -78.25  75.00 -77.57   52
 33  ω   -106.00 -81.00   0.50    0.70    --  -78.25 126.00-111.13   50
 34  ω   -106.00 -53.00   0.50    0.70    --  -78.25 127.00 -31.98  106
 35  ω    -64.00 -39.00   0.50    0.70    --  -78.25 129.00-137.95   50
 36  ω    -97.00 -72.00   0.50    0.70    --  -78.25 117.00 -70.46   50
 37  ω   -108.00 -83.00   0.50    0.70    --  -78.25 -87.00  20.98   50
 38  ω   -108.00 -82.00   0.50    0.70    --  -78.25 129.00-137.95   52
 39  ω   -106.00 -80.00   0.50    0.70    --  -78.25 -28.00  78.96   52
 40  ω    -75.00 -43.00   0.50    0.70    --  -78.25 138.00  10.43   64
 41  ω   -114.00 -89.00   0.50    0.70    --  -78.25 138.00 -25.24   50
 42  ω   -112.00 -84.00   0.50    0.70    --  -78.25-104.00  -4.16   56
 43  ω    -77.00 -51.00   0.50    0.70    --  -78.25 126.00-111.13   52
 44  ω   -109.00 -83.00   0.50    0.70    --  -78.25 130.00  64.34   52
 45  ω   -106.00 -80.00   0.50    0.70    --  -78.25 126.00   6.30   52
 46  ω    -69.00 -43.00   0.50    0.70    --  -78.25 135.00 156.00   52
 47  ω     98.00 123.00   0.50    0.70    --   79.75  15.00  38.22   50
 48  ω     49.00 117.00   0.50    0.70    --   79.75  13.00 165.36  136
 49  ω     89.00 126.00   0.50    0.70    --   79.75  20.00  79.71   74
 50  ω     47.00  82.00   0.50    0.70    --   79.75  -4.00-128.91   70
 51  ω     43.00  99.00   0.50    0.70    --   79.75-113.00  94.76  112
 52  ω     45.00  89.00   0.50    0.70    --   79.75-107.00  30.85   88
 53  ω     61.00 101.00   0.50    0.70    --   79.75-116.00 163.55   80
 54  ω     48.00  86.00   0.50    0.70    --   79.75-112.00 119.94   76
 55  ω     44.00 116.00   0.50    0.70    --   79.75  -2.00 106.32  144
 56  ω     65.00 120.00   0.50    0.70    --   79.75  13.00 -28.89  110
 57  ω     64.00 101.00   0.50    0.70    --   79.75  22.00 -89.47   74
 58  ω     58.00 116.00   0.50    0.70    --   79.75-138.00-124.80  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.979
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              22
_reflns_limit_l_min              -21
_reflns_number_gt                2813
_reflns_number_total             2919
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.1599
_refine_diff_density_min         -0.1812
_refine_diff_density_rms         0.0310
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.14(4)
_refine_ls_d_res_high            0.7981
_refine_ls_d_res_low             10.7595
_refine_ls_goodness_of_fit_ref   1.0738
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    8
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2919
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.0738
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+0.2237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0707
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H12a)=1-FVAR(1)
 Sof(F2)=FVAR(1)
 Sof(H11b)=1-FVAR(2)
 Sof(F1)=FVAR(2)
 Sof(H11a)=1-FVAR(3)
 Sof(F3)=FVAR(3)
3.a Secondary CH2 refined with riding coordinates and stretchable bonds:
 C11(H11a,H11b), C12(H12a,H12)
;
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_refinement_flags_posn
_atom_site_disorder_group
O1 O 0.17836(15) 0.36657(6) 0.80360(5) 0.0300(2) Uani 1.000000 . .
O2 O 0.05636(17) 0.21174(7) 0.81510(5) 0.0410(3) Uani 1.000000 . .
F1 F 0.3959(2) 0.33169(8) 0.41022(6) 0.0385(4) Uani 0.660(4) . 1
C9 C 0.46087(19) 0.39686(8) 0.61449(6) 0.0221(2) Uani 1.000000 . .
C8 C 0.3865(2) 0.50634(8) 0.60299(6) 0.0227(2) Uani 1.000000 . .
H8 H 0.218(2) 0.5027(10) 0.5930(7) 0.021(3) Uiso 1.000000 . .
C1 C 0.1673(2) 0.27098(9) 0.78126(7) 0.0304(3) Uani 1.000000 . .
C3 C 0.3159(2) 0.36211(8) 0.68132(6) 0.0225(2) Uani 1.000000 . .
H3 H 0.160(2) 0.3770(10) 0.6658(7) 0.022(3) Uiso 1.000000 . .
C7 C 0.4141(2) 0.56739(9) 0.67578(7) 0.0273(3) Uani 1.000000 . .
H7a H 0.581(2) 0.5710(10) 0.6896(8) 0.026(3) Uiso 1.000000 . .
H7b H 0.362(3) 0.6365(11) 0.6672(8) 0.032(4) Uiso 1.000000 . .
C10 C 0.3930(2) 0.33761(9) 0.54375(7) 0.0268(2) Uani 1.000000 . .
H10a H 0.449(2) 0.2661(10) 0.5475(7) 0.025(3) Uiso 1.000000 . .
H10b H 0.214(2) 0.3316(9) 0.5386(7) 0.014(3) Uiso 1.000000 . .
C4 C 0.3440(2) 0.41901(9) 0.75588(6) 0.0256(2) Uani 1.000000 . .
C13 C 0.4741(2) 0.55645(8) 0.52949(7) 0.0264(3) Uani 1.000000 . .
C14 C 0.7127(2) 0.38173(10) 0.62987(7) 0.0279(3) Uani 1.000000 . .
H14a H 0.801(3) 0.3731(11) 0.5829(9) 0.036(4) Uiso 1.000000 . .
H14b H 0.779(3) 0.4380(12) 0.6574(9) 0.036(4) Uiso 1.000000 . .
H14c H 0.737(3) 0.3209(11) 0.6600(9) 0.037(4) Uiso 1.000000 . .
C2 C 0.3043(2) 0.25606(9) 0.70930(7) 0.0292(3) Uani 1.000000 . .
H2a H 0.448(3) 0.2288(12) 0.7238(9) 0.038(4) Uiso 1.000000 . .
H2b H 0.225(3) 0.2084(11) 0.6751(8) 0.036(4) Uiso 1.000000 . .
C11 C 0.4818(2) 0.38427(10) 0.47134(7) 0.0316(3) Uani 1.000000 . .
H11a H 0.665(5) 0.38139(13) 0.47178(7) 0.0379(3) Uiso 0.921(4) GR 2
H11b H 0.4233(16) 0.3417(12) 0.4228(14) 0.0379(3) Uiso 0.340(4) GR 2
C6 C 0.2776(2) 0.52547(9) 0.74286(7) 0.0291(3) Uani 1.000000 . .
H6a H 0.303(3) 0.5658(11) 0.7889(8) 0.028(3) Uiso 1.000000 . .
H6b H 0.110(3) 0.5282(11) 0.7305(8) 0.030(4) Uiso 1.000000 . .
C15 C 0.7273(2) 0.57625(10) 0.52802(7) 0.0319(3) Uani 1.000000 . .
H15a H 0.773(3) 0.6143(12) 0.5747(9) 0.042(4) Uiso 1.000000 . .
H15b H 0.825(3) 0.5158(12) 0.5221(9) 0.044(4) Uiso 1.000000 . .
H15c H 0.765(3) 0.6145(14) 0.4813(10) 0.051(5) Uiso 1.000000 . .
C12 C 0.4077(2) 0.49003(9) 0.46235(7) 0.0310(3) Uani 1.000000 . .
H12a H 0.238(2) 0.49169(10) 0.45633(11) 0.0373(3) Uiso 0.793(3) GR 2
H12 H 0.4763(9) 0.5178(4) 0.4141(7) 0.030(4) Uiso 1.000000 GR .
C5 C 0.5656(2) 0.41101(11) 0.79898(7) 0.0341(3) Uani 1.000000 . .
H5a H 0.538(3) 0.4361(12) 0.8506(10) 0.046(5) Uiso 1.000000 . .
H5b H 0.626(3) 0.3419(12) 0.8001(9) 0.039(4) Uiso 1.000000 . .
H5c H 0.683(3) 0.4540(11) 0.7771(8) 0.032(4) Uiso 1.000000 . .
C16 C 0.3556(3) 0.65602(10) 0.51853(8) 0.0363(3) Uani 1.000000 . .
H16a H 0.190(3) 0.6504(11) 0.5258(9) 0.037(4) Uiso 1.000000 . .
H16b H 0.414(3) 0.7064(13) 0.5542(9) 0.046(5) Uiso 1.000000 . .
H16c H 0.385(3) 0.6812(12) 0.4675(10) 0.045(4) Uiso 1.000000 . .
F2 F 0.1764(6) 0.4764(3) 0.4495(2) 0.0343(13) Uani 0.207(3) . 1
F3 F 0.662(3) 0.3727(7) 0.4513(6) 0.042(4) Uani 0.079(4) . 1


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 C1 1.3580(16) . ?
O1 C4 1.4808(14) . ?
O2 C1 1.2007(15) . ?
F1 C11 1.3911(17) . ?
C9 C8 1.5643(15) . ?
C9 C3 1.5363(16) . ?
C9 C10 1.5389(16) . ?
C9 C14 1.5407(16) . ?
C8 H8 1.020(14) . ?
C8 C7 1.5372(16) . ?
C8 C13 1.5548(16) . ?
C1 C2 1.5234(17) . ?
C3 H3 0.991(14) . ?
C3 C4 1.5346(15) . ?
C3 C2 1.5237(15) . ?
C7 H7a 1.026(15) . ?
C7 H7b 1.000(15) . ?
C7 C6 1.5451(17) . ?
C10 H10a 1.029(14) . ?
C10 H10b 1.076(13) . ?
C10 C11 1.5210(17) . ?
C4 C6 1.5162(17) . ?
C4 C5 1.5289(17) . ?
C13 C15 1.5346(18) . ?
C13 C12 1.5404(17) . ?
C13 C16 1.5378(17) . ?
C14 H14a 0.990(16) . ?
C14 H14b 0.989(16) . ?
C14 H14c 0.992(16) . ?
C2 H2a 0.968(17) . ?
C2 H2b 1.004(15) . ?
C11 H11a 1.09(3) . ?
C11 H11b 1.09(3) . ?
C11 C12 1.5109(18) . ?
C11 F3 1.141(18) . ?
C6 H6a 0.992(14) . ?
C6 H6b 1.026(16) . ?
C15 H15a 1.010(17) . ?
C15 H15b 1.011(18) . ?
C15 H15c 0.999(18) . ?
C12 H12a 1.018(14) . ?
C12 H12 1.018(14) . ?
C12 F2 1.411(4) . ?
C5 H5a 0.986(18) . ?
C5 H5b 1.005(16) . ?
C5 H5c 0.989(17) . ?
C16 H16a 0.998(17) . ?
C16 H16b 0.994(18) . ?
C16 H16c 0.979(17) . ?

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
C4 O1 C1 109.08(9) . . ?
C3 C9 C8 103.40(9) . . ?
C10 C9 C8 108.48(9) . . ?
C10 C9 C3 108.28(9) . . ?
C14 C9 C8 115.22(10) . . ?
C14 C9 C3 111.89(9) . . ?
C14 C9 C10 109.24(10) . . ?
H8 C8 C9 104.8(7) . . ?
C7 C8 C9 111.95(9) . . ?
C7 C8 H8 106.0(8) . . ?
C13 C8 C9 115.38(9) . . ?
C13 C8 H8 102.0(8) . . ?
C13 C8 C7 115.13(9) . . ?
O2 C1 O1 121.52(12) . . ?
C2 C1 O1 110.06(10) . . ?
C2 C1 O2 128.39(12) . . ?
H3 C3 C9 104.7(8) . . ?
C4 C3 C9 116.20(10) . . ?
C4 C3 H3 103.7(8) . . ?
C2 C3 C9 124.35(10) . . ?
C2 C3 H3 103.9(8) . . ?
C2 C3 C4 101.72(9) . . ?
H7a C7 C8 109.2(8) . . ?
H7b C7 C8 110.3(8) . . ?
H7b C7 H7a 106.9(11) . . ?
C6 C7 C8 112.62(10) . . ?
C6 C7 H7a 110.2(8) . . ?
C6 C7 H7b 107.4(9) . . ?
H10a C10 C9 110.8(8) . . ?
H10b C10 C9 111.7(7) . . ?
H10b C10 H10a 105.0(10) . . ?
C11 C10 C9 111.81(10) . . ?
C11 C10 H10a 109.5(8) . . ?
C11 C10 H10b 107.9(7) . . ?
C3 C4 O1 99.92(9) . . ?
C6 C4 O1 111.72(10) . . ?
C6 C4 C3 108.76(9) . . ?
C5 C4 O1 105.08(9) . . ?
C5 C4 C3 119.02(10) . . ?
C5 C4 C6 111.66(11) . . ?
C15 C13 C8 114.94(10) . . ?
C12 C13 C8 107.37(9) . . ?
C12 C13 C15 110.05(10) . . ?
C16 C13 C8 109.57(10) . . ?
C16 C13 C15 107.24(11) . . ?
C16 C13 C12 107.44(10) . . ?
H14a C14 C9 112.9(9) . . ?
H14b C14 C9 112.1(9) . . ?
H14b C14 H14a 106.7(13) . . ?
H14c C14 C9 110.3(9) . . ?
H14c C14 H14a 105.8(12) . . ?
H14c C14 H14b 108.7(12) . . ?
C3 C2 C1 99.71(10) . . ?
H2a C2 C1 107.8(9) . . ?
H2a C2 C3 114.0(9) . . ?
H2b C2 C1 109.4(9) . . ?
H2b C2 C3 115.9(8) . . ?
H2b C2 H2a 109.3(13) . . ?
C10 C11 F1 107.98(11) . . ?
H11a C11 F1 110.82(8) . . ?
H11a C11 C10 109.10(8) . . ?
H11b C11 F1 3.00(9) . . ?
H11b C11 C10 109.10(7) . . ?
H11b C11 H11a 107.8 . . ?
C12 C11 F1 107.36(11) . . ?
C12 C11 C10 112.47(11) . . ?
C12 C11 H11a 109.10(8) . . ?
C12 C11 H11b 109.10(7) . . ?
F3 C11 F1 92.1(6) . . ?
F3 C11 C10 122.1(6) . . ?
F3 C11 H11a 19.5(6) . . ?
F3 C11 H11b 89.1(6) . . ?
F3 C11 C12 111.9(5) . . ?
C4 C6 C7 109.24(10) . . ?
H6a C6 C7 110.1(8) . . ?
H6a C6 C4 111.2(8) . . ?
H6b C6 C7 109.8(8) . . ?
H6b C6 C4 108.8(8) . . ?
H6b C6 H6a 107.7(12) . . ?
H15a C15 C13 110.0(10) . . ?
H15b C15 C13 115.1(10) . . ?
H15b C15 H15a 110.2(13) . . ?
H15c C15 C13 109.0(11) . . ?
H15c C15 H15a 110.2(14) . . ?
H15c C15 H15b 102.0(14) . . ?
C11 C12 C13 113.60(10) . . ?
H12a C12 C13 108.85(7) . . ?
H12a C12 C11 108.85(8) . . ?
H12 C12 C13 108.85(6) . . ?
H12 C12 C11 108.85(7) . . ?
H12 C12 H12a 107.7 . . ?
F2 C12 C13 116.89(19) . . ?
F2 C12 C11 100.27(19) . . ?
F2 C12 H12a 9.43(17) . . ?
F2 C12 H12 107.88(16) . . ?
H5a C5 C4 106.7(11) . . ?
H5b C5 C4 112.5(9) . . ?
H5b C5 H5a 111.5(13) . . ?
H5c C5 C4 112.0(9) . . ?
H5c C5 H5a 106.0(13) . . ?
H5c C5 H5b 107.9(13) . . ?
H16a C16 C13 111.8(9) . . ?
H16b C16 C13 111.3(10) . . ?
H16b C16 H16a 108.6(14) . . ?
H16c C16 C13 109.9(10) . . ?
H16c C16 H16a 108.9(13) . . ?
H16c C16 H16b 106.1(13) . . ?

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 C1 C2 C3 -20.15(11) . . . . ?
O1 C4 C3 C9 178.75(8) . . . . ?
O1 C4 C3 C2 -43.14(10) . . . . ?
O1 C4 C6 C7 -163.83(10) . . . . ?
O2 C1 C2 C3 157.62(16) . . . . ?
F1 C11 C10 C9 -174.52(11) . . . . ?
F1 C11 C12 C13 175.31(11) . . . . ?
F1 C11 C12 F2 49.81(19) . . . . ?
C9 C8 C7 C6 -58.79(11) . . . . ?
C9 C8 C13 C15 -69.18(11) . . . . ?
C9 C8 C13 C12 53.61(11) . . . . ?
C9 C8 C13 C16 170.01(11) . . . . ?
C9 C3 C4 C6 61.62(11) . . . . ?
C9 C3 C4 C5 -67.73(11) . . . . ?
C9 C3 C2 C1 171.83(13) . . . . ?
C9 C10 C11 C12 -56.24(12) . . . . ?
C9 C10 C11 F3 81.1(6) . . . . ?
C8 C7 C6 C4 56.08(11) . . . . ?
C8 C13 C12 C11 -53.14(11) . . . . ?
C8 C13 C12 F2 62.95(19) . . . . ?
C1 C2 C3 C4 38.36(10) . . . . ?
C3 C4 C6 C7 -54.50(11) . . . . ?
C7 C6 C4 C5 78.82(11) . . . . ?
C10 C11 C12 C13 56.68(12) . . . . ?
C10 C11 C12 F2 -68.83(18) . . . . ?
C13 C12 C11 F3 -85.1(6) . . . . ?


_olex2_date_sample_data_collection 2022-09-28
_olex2_date_sample_submission    2022-09-14
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder inert oil'
_olex2_submission_original_sample_id 'SY 244'
_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
- B-factor correction
;
