# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_jb230920_1_1
_database_code_depnum_ccdc_archive 'CCDC 2064033'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Small Molecule Crystallography Center
Switzerland
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-04-09 downloaded from the CCDC.
;
_audit_creation_date             2020-09-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
angus.mcmillan@org.chem.ethz.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 F3 O2, C19 H28 N3 O'
_chemical_formula_sum            'C21 H28 F3 N3 O3'
_chemical_formula_weight         427.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H27N3O
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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   52.9651(13)
_cell_length_b                   8.6539(2)
_cell_length_c                   19.4197(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.443(2)
_cell_angle_gamma                90
_cell_volume                     8898.3(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    8616
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      55.0410
_cell_measurement_theta_min      4.5360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3616
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -2 -1 0.0381
0 0 1 0.0409
-4 2 0 0.0343
2 0 0 0.0092
-2 0 0 0.0083
16 2 10 0.0258
-22 -3 6 0.0461
21 3 -7 0.0396
3 -1 -12 0.0352
1 -1 12 0.0419
18 5 -3 0.0363
4 -4 9 0.0547

_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.017
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.9854 -1.9993 -0.9986 -0.0305 0.3568 -0.1329
-0.0003 -0.0002 0.9995 -0.0024 0.0120 0.0784
-3.9851 1.9995 -0.0008 0.0330 -0.3689 0.0546
1.9979 -0.0001 0.0006 -0.0566 0.0129 -0.0022
-1.9979 0.0001 -0.0006 0.0566 -0.0129 0.0022
15.5185 2.2441 9.9118 -0.5540 -0.1663 0.8158
-22.2272 -3.4310 5.9640 0.7528 0.5174 0.4069
21.1118 3.1011 -7.3010 -0.7047 -0.4840 -0.5187
3.3954 -1.3844 -12.1792 -0.0111 0.1133 -0.9935
1.1060 -0.9545 12.4009 -0.0235 0.3199 0.9472
17.7198 4.6387 -3.0477 -0.6805 -0.7187 -0.1429
3.9780 -3.9015 8.9122 0.0215 0.8023 0.5965

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       55
_diffrn_reflns_limit_h_min       -57
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34793
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        58.459
_diffrn_reflns_theta_max         58.459
_diffrn_reflns_theta_min         1.669
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  35.00   0.50   24.00    --   -1.09  38.00  30.00   92
  2  ω    -13.00  16.00   0.50   24.00    --   -1.09  57.00  90.00   58
  3  ω     -9.00  36.00   0.50   24.00    --   65.61 -38.00 -30.00   90
  4  ω     52.00 141.00   0.50   24.00    --   65.61  19.00 -90.00  178
  5  ω     53.00  91.00   0.50   24.00    --   65.61  19.00-180.00   76
  6  ω     -6.00  42.00   0.50   24.00    --   -1.09  19.00-180.00   96
  7  ω    -22.00   3.00   0.50   24.00    --   -1.09 -19.00-150.00   50
  8  ω     -6.00  68.00   0.50   24.00    --   65.61 -57.00  30.00  148
  9  ω     53.00 115.00   0.50   24.00    --   65.61-130.00 131.00  124
 10  ω    -19.00   7.00   0.50   24.00    --  -67.79  38.00 -60.00   52
 11  ω    -38.00   1.00   0.50   24.00    --  -67.79  38.00-120.00   78
 12  ω    -63.00 -23.00   0.50   24.00    --   -1.09 -19.00-150.00   80
 13  ω    -90.00  -2.00   0.50   24.00    --  -67.79  77.00 -60.00  176
 14  ω    -36.00  -9.00   0.50   24.00    --  -67.79  38.00 120.00   54
 15  ω    -38.00   8.00   0.50   24.00    --  -67.79  38.00 150.00   92
 16  ω     80.00 136.00   0.50   24.00    --   65.61 178.00  90.00  112
 17  ω     83.00 131.00   0.50   24.00    --   65.61 178.00 120.00   96
 18  ω     88.00 136.00   0.50   24.00    --   65.61 178.00 -90.00   96
 19  ω    101.00 126.00   0.50   24.00    --   65.61 178.00-120.00   50
 20  ω    -74.00 -47.00   0.50   24.00    --  -67.79 -77.00-150.00   54
 21  ω   -124.00 -90.00   0.50   24.00    --  -67.79 -77.00-150.00   68
 22  ω   -133.00 -44.00   0.50   24.00    --  -67.79 -77.00-180.00  178
 23  ω    -90.00 -19.00   0.50   24.00    --  -67.79 130.00-156.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0283490000
_diffrn_orient_matrix_UB_12      -0.0400093000
_diffrn_orient_matrix_UB_13      -0.0024450000
_diffrn_orient_matrix_UB_21      0.0064392000
_diffrn_orient_matrix_UB_22      -0.1716457000
_diffrn_orient_matrix_UB_23      0.0120071000
_diffrn_orient_matrix_UB_31      -0.0011359000
_diffrn_orient_matrix_UB_32      0.0250551000
_diffrn_orient_matrix_UB_33      0.0784092000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4100
_reflns_number_total             6226
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     54.18
_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 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     627
_refine_ls_number_reflns         6226
_refine_ls_number_restraints     175
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0618
_refine_ls_restrained_S_all      1.045
_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)+(0.1119P)²+5.3235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1935
_refine_special_details          'Disorder in one trifluoracetate anion.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2A-H2A = N3A-H3AB = N3A-H3AA = N3B-H3BB = N3B-H3BA = N2B-H2B
 0.93 with sigma of 0.02
 H3BB-H3BA
 1.44 with sigma of 0.02
 H3AB-H3AA
 1.44 with sigma of 0.02
 C2E-C1E \\sim C2D-C1D
 with sigma of 0.02
 F2D-C1D \\sim F3E-C1E \\sim F2E-C1E \\sim F3D-C1D \\sim F1E-C1E \\sim F1D-C1D
 with sigma of 0.02
 O2D-O1D \\sim O2E-O1E
 with sigma of 0.02
 F1D-F2D \\sim F2D-F3D \\sim F3D-F1D \\sim F1E-F2E \\sim F2E-F3E \\sim F3E-F1E
 with sigma of 0.02
 F1C-C2C \\sim F2C-C2C \\sim F3C-C2C \\sim F1D-C2D \\sim F2D-C2D \\sim F3D-C2D
 with sigma of 0.02
 O2D-C2D \\sim O1D-C2D \\sim O1E-C2E \\sim O2E-C2E
 with sigma of 0.02
 O1C-C1C \\sim O2C-C1C \\sim O1D-C1D \\sim O2D-C1D
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C17A, C18A, C19A, N3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1D, F2D, F3D, O1D, O2D, C1D, C2D
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1E, F2E, F3E, O1E, O2E, C1E, C2E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F1E)=Sof(F2E)=Sof(F3E)=Sof(O1E)=Sof(O2E)=Sof(C1E)=Sof(C2E)=1-FVAR(1)
 Sof(F1D)=Sof(F2D)=Sof(F3D)=Sof(O1D)=Sof(O2D)=Sof(C1D)=Sof(C2D)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8A(H8A), C14A(H14A), C17A(H17A), C8B(H8B), C14B(H14B), C17B(H17B)
5.b Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C10A(H10A,H10B), C12A(H12A,H12B), C13A(H13A,H13B), C15A(H15A,
 H15B), C16A(H16A,H16B), C9B(H9BA,H9BB), C10B(H10C,H10D), C12B(H12C,H12D),
 C13B(H13C,H13D), C15B(H15C,H15D), C16B(H16C,H16D)
5.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B)
5.d Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C19A(H19A,H19B,H19C), C18B(H18D,H18E,H18F), C19B(H19D,
 H19E,H19F)
;
_atom_sites_solution_hydrogens   mixed
_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
F1C F 0.38684(6) 0.4629(4) 0.61656(14) 0.1140(10) Uani 1 1 d D . . . .
F2C F 0.42322(6) 0.5553(3) 0.58934(12) 0.1024(9) Uani 1 1 d D . . . .
F3C F 0.41764(6) 0.3132(3) 0.59499(12) 0.1141(10) Uani 1 1 d D . . . .
O1C O 0.42655(6) 0.5715(3) 0.72444(13) 0.0782(8) Uani 1 1 d D . . . .
O2C O 0.41632(5) 0.3259(3) 0.73172(12) 0.0736(8) Uani 1 1 d D . . . .
C1C C 0.41238(11) 0.4436(5) 0.6258(2) 0.0811(13) Uani 1 1 d D . . . .
C2C C 0.41926(7) 0.4490(4) 0.70118(17) 0.0536(9) Uani 1 1 d D . . . .
F1D F 0.52484(14) -0.0090(8) 0.5077(3) 0.148(3) Uani 0.623(6) 1 d D . P A 1
F1E F 0.5357(4) -0.116(2) 0.4949(10) 0.230(10) Uani 0.377(6) 1 d D . P A 2
F2D F 0.55029(16) -0.1983(10) 0.5059(4) 0.159(3) Uani 0.623(6) 1 d D . P A 1
F2E F 0.5518(2) 0.0968(9) 0.5168(4) 0.130(4) Uani 0.377(6) 1 d D . P A 2
F3D F 0.51671(11) -0.2127(7) 0.5530(3) 0.138(2) Uani 0.623(6) 1 d D . P A 1
F3E F 0.5730(3) -0.0964(13) 0.5208(5) 0.174(6) Uani 0.377(6) 1 d D . P A 2
O1D O 0.56419(10) 0.0431(5) 0.5947(3) 0.096(2) Uani 0.623(6) 1 d D . P A 1
O1E O 0.5417(3) -0.1896(11) 0.6368(8) 0.117(5) Uani 0.377(6) 1 d D . P A 2
O2D O 0.54237(12) -0.1152(9) 0.6618(3) 0.082(2) Uani 0.623(6) 1 d D . P A 1
O2E O 0.55266(14) 0.0555(8) 0.6496(3) 0.068(2) Uani 0.377(6) 1 d D . P A 2
C1D C 0.53548(16) -0.1231(9) 0.5427(4) 0.085(2) Uani 0.623(6) 1 d D . P A 1
C1E C 0.5510(3) -0.0473(14) 0.5376(6) 0.102(4) Uani 0.377(6) 1 d D . P A 2
C2D C 0.5483(3) -0.0544(12) 0.6088(4) 0.065(4) Uani 0.623(6) 1 d D . P A 1
C2E C 0.5482(4) -0.0618(17) 0.6173(8) 0.059(5) Uani 0.377(6) 1 d D . P A 2
O1A O 0.35267(4) 0.8255(3) 0.68794(11) 0.0579(6) Uani 1 1 d . . . . .
N1A N 0.23965(7) 0.3764(4) 0.4101(2) 0.0859(11) Uani 1 1 d . . . . .
N2A N 0.31756(5) 0.9818(3) 0.60234(15) 0.0569(8) Uani 1 1 d D . . . .
H2A H 0.3024(5) 1.030(4) 0.5954(18) 0.068 Uiso 1 1 d D U . . .
N3A N 0.43684(6) 0.8756(4) 0.70470(16) 0.0663(8) Uani 1 1 d D . . . .
H3AA H 0.4409(7) 0.903(4) 0.7476(12) 0.080 Uiso 1 1 d D U . . .
H3AB H 0.4338(7) 0.768(2) 0.7072(17) 0.080 Uiso 1 1 d D U . . .
C1A C 0.25112(8) 0.4504(5) 0.4478(2) 0.0680(11) Uani 1 1 d . . . . .
C2A C 0.26629(7) 0.5463(4) 0.49372(19) 0.0574(9) Uani 1 1 d . . . . .
C3A C 0.27833(7) 0.6741(4) 0.46805(18) 0.0592(9) Uani 1 1 d . . . . .
H3A H 0.276805 0.697256 0.421365 0.071 Uiso 1 1 calc R U . . .
C4A C 0.29263(6) 0.7682(4) 0.51107(17) 0.0544(9) Uani 1 1 d . . . . .
H4A H 0.300784 0.853851 0.493142 0.065 Uiso 1 1 calc R U . . .
C5A C 0.29494(6) 0.7359(4) 0.58075(16) 0.0501(8) Uani 1 1 d . . . . .
C6A C 0.28239(7) 0.6069(4) 0.60566(19) 0.0654(10) Uani 1 1 d . . . . .
H6A H 0.283515 0.585503 0.652561 0.078 Uiso 1 1 calc R U . . .
C7A C 0.26851(7) 0.5107(4) 0.5639(2) 0.0659(10) Uani 1 1 d . . . . .
H7A H 0.260708 0.423619 0.581614 0.079 Uiso 1 1 calc R U . . .
C8A C 0.31161(7) 0.8290(4) 0.62895(16) 0.0533(9) Uani 1 1 d . . . . .
H8A H 0.303111 0.840746 0.672889 0.064 Uiso 1 1 calc R U . . .
C9A C 0.33639(7) 0.7450(4) 0.64171(17) 0.0569(9) Uani 1 1 d . . . . .
H9AA H 0.332993 0.643264 0.660249 0.068 Uiso 1 1 calc R U . . .
H9AB H 0.344750 0.731553 0.598249 0.068 Uiso 1 1 calc R U . . .
C10A C 0.33362(6) 1.0663(4) 0.65310(19) 0.0600(9) Uani 1 1 d . . . . .
H10A H 0.324682 1.076936 0.695821 0.072 Uiso 1 1 calc R U . . .
H10B H 0.337058 1.169065 0.635774 0.072 Uiso 1 1 calc R U . . .
C11A C 0.35813(6) 0.9831(4) 0.66684(16) 0.0517(9) Uani 1 1 d . . . . .
C12A C 0.37554(6) 0.9836(4) 0.60639(17) 0.0562(9) Uani 1 1 d . . . . .
H12A H 0.379286 1.089582 0.594004 0.067 Uiso 1 1 calc R U . . .
H12B H 0.367016 0.935305 0.567177 0.067 Uiso 1 1 calc R U . . .
C13A C 0.40013(7) 0.8985(5) 0.62210(17) 0.0607(10) Uani 1 1 d . . . . .
H13A H 0.411109 0.906774 0.583035 0.073 Uiso 1 1 calc R U . . .
H13B H 0.396646 0.789841 0.629679 0.073 Uiso 1 1 calc R U . . .
C14A C 0.41353(7) 0.9669(4) 0.68663(17) 0.0564(9) Uani 1 1 d . . . . .
H14A H 0.418443 1.073657 0.676716 0.068 Uiso 1 1 calc R U . . .
C15A C 0.39642(7) 0.9670(5) 0.74732(17) 0.0630(10) Uani 1 1 d . . . . .
H15A H 0.404896 1.017069 0.786162 0.076 Uiso 1 1 calc R U . . .
H15B H 0.392729 0.861381 0.760368 0.076 Uiso 1 1 calc R U . . .
C16A C 0.37201(7) 1.0510(5) 0.73009(18) 0.0637(10) Uani 1 1 d . . . . .
H16A H 0.375668 1.159076 0.721598 0.076 Uiso 1 1 calc R U . . .
H16B H 0.361065 1.045577 0.769329 0.076 Uiso 1 1 calc R U . . .
C17A C 0.45923(7) 0.8935(5) 0.6597(2) 0.0689(10) Uani 1 1 d . . . . .
H17A H 0.453239 0.887188 0.611612 0.083 Uiso 1 1 calc R U . . .
C18A C 0.47677(10) 0.7589(7) 0.6733(4) 0.146(3) Uani 1 1 d . . . . .
H18A H 0.481535 0.756500 0.721357 0.219 Uiso 1 1 calc R U . . .
H18B H 0.491600 0.770334 0.646380 0.219 Uiso 1 1 calc R U . . .
H18C H 0.468334 0.664366 0.660991 0.219 Uiso 1 1 calc R U . . .
C19A C 0.47126(8) 1.0477(5) 0.6702(2) 0.0814(12) Uani 1 1 d . . . . .
H19A H 0.459439 1.127347 0.657399 0.122 Uiso 1 1 calc R U . . .
H19B H 0.485895 1.055470 0.642259 0.122 Uiso 1 1 calc R U . . .
H19C H 0.476200 1.059570 0.717846 0.122 Uiso 1 1 calc R U . . .
O1B O 0.65218(4) 0.5152(3) 0.63173(10) 0.0550(6) Uani 1 1 d . . . . .
N1B N 0.71971(7) 1.4316(5) 0.73761(18) 0.0882(11) Uani 1 1 d . . . . .
N2B N 0.66888(6) 0.7461(4) 0.54256(14) 0.0640(8) Uani 1 1 d D . . . .
H2B H 0.6795(6) 0.795(4) 0.5138(16) 0.077 Uiso 1 1 d D U . . .
N3B N 0.56758(6) 0.3561(4) 0.63286(15) 0.0590(8) Uani 1 1 d D . . . .
H3BA H 0.5744(7) 0.363(4) 0.6759(11) 0.071 Uiso 1 1 d D U . . .
H3BB H 0.5656(7) 0.255(2) 0.6225(16) 0.071 Uiso 1 1 d D U . . .
C1B C 0.71384(8) 1.3099(5) 0.72052(19) 0.0692(11) Uani 1 1 d . . . . .
C2B C 0.70588(7) 1.1607(4) 0.69424(17) 0.0574(9) Uani 1 1 d . . . . .
C3B C 0.68368(7) 1.1516(4) 0.65573(16) 0.0560(9) Uani 1 1 d . . . . .
H3B H 0.673762 1.239140 0.648707 0.067 Uiso 1 1 calc R U . . .
C4B C 0.67627(7) 1.0111(4) 0.62761(17) 0.0569(9) Uani 1 1 d . . . . .
H4B H 0.661313 1.005206 0.601620 0.068 Uiso 1 1 calc R U . . .
C5B C 0.69072(6) 0.8798(4) 0.63751(16) 0.0527(9) Uani 1 1 d . . . . .
C6B C 0.71300(7) 0.8904(5) 0.67701(18) 0.0609(10) Uani 1 1 d . . . . .
H6B H 0.722891 0.802879 0.684329 0.073 Uiso 1 1 calc R U . . .
C7B C 0.72057(7) 1.0311(5) 0.70559(17) 0.0602(10) Uani 1 1 d . . . . .
H7B H 0.735396 1.037645 0.732104 0.072 Uiso 1 1 calc R U . . .
C8B C 0.68200(7) 0.7257(4) 0.60900(16) 0.0572(9) Uani 1 1 d . . . . .
H8B H 0.696546 0.657087 0.603729 0.069 Uiso 1 1 calc R U . . .
C9B C 0.66351(7) 0.6538(4) 0.65830(16) 0.0544(9) Uani 1 1 d . . . . .
H9BA H 0.672299 0.630680 0.701494 0.065 Uiso 1 1 calc R U . . .
H9BB H 0.650323 0.728119 0.667730 0.065 Uiso 1 1 calc R U . . .
C10B C 0.65923(7) 0.5982(4) 0.51578(17) 0.0642(10) Uani 1 1 d . . . . .
H10C H 0.672993 0.524994 0.511874 0.077 Uiso 1 1 calc R U . . .
H10D H 0.651535 0.612949 0.470399 0.077 Uiso 1 1 calc R U . . .
C11B C 0.63974(7) 0.5360(4) 0.56500(16) 0.0524(9) Uani 1 1 d . . . . .
C12B C 0.61706(7) 0.6424(4) 0.56916(17) 0.0555(9) Uani 1 1 d . . . . .
H12C H 0.609956 0.658193 0.523174 0.067 Uiso 1 1 calc R U . . .
H12D H 0.622591 0.742009 0.586755 0.067 Uiso 1 1 calc R U . . .
C13B C 0.59648(7) 0.5787(4) 0.61547(18) 0.0555(9) Uani 1 1 d . . . . .
H13C H 0.602955 0.571068 0.662514 0.067 Uiso 1 1 calc R U . . .
H13D H 0.582142 0.648511 0.614868 0.067 Uiso 1 1 calc R U . . .
C14B C 0.58815(7) 0.4206(4) 0.59015(17) 0.0559(9) Uani 1 1 d . . . . .
H14B H 0.581630 0.431294 0.542718 0.067 Uiso 1 1 calc R U . . .
C15B C 0.61061(7) 0.3098(4) 0.58991(18) 0.0587(9) Uani 1 1 d . . . . .
H15C H 0.617321 0.296709 0.636480 0.070 Uiso 1 1 calc R U . . .
H15D H 0.605149 0.209474 0.572914 0.070 Uiso 1 1 calc R U . . .
C16B C 0.63103(7) 0.3737(4) 0.54419(18) 0.0588(9) Uani 1 1 d . . . . .
H16C H 0.624652 0.376253 0.496948 0.071 Uiso 1 1 calc R U . . .
H16D H 0.645449 0.304567 0.546075 0.071 Uiso 1 1 calc R U . . .
C17B C 0.54251(7) 0.4362(5) 0.62870(19) 0.0688(11) Uani 1 1 d . . . . .
H17B H 0.544890 0.545706 0.639915 0.083 Uiso 1 1 calc R U . . .
C18B C 0.52536(9) 0.3642(6) 0.6808(2) 0.0954(15) Uani 1 1 d . . . . .
H18D H 0.523518 0.255876 0.671208 0.143 Uiso 1 1 calc R U . . .
H18E H 0.509103 0.413156 0.677938 0.143 Uiso 1 1 calc R U . . .
H18F H 0.532561 0.377781 0.726214 0.143 Uiso 1 1 calc R U . . .
C19B C 0.53086(10) 0.4227(7) 0.5569(2) 0.1055(17) Uani 1 1 d . . . . .
H19D H 0.540758 0.480701 0.525261 0.158 Uiso 1 1 calc R U . . .
H19E H 0.513959 0.462702 0.556788 0.158 Uiso 1 1 calc R U . . .
H19F H 0.530495 0.316065 0.543296 0.158 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1C C1C 1.370(5) . ?
F2C C1C 1.336(5) . ?
F3C C1C 1.311(5) . ?
O1C C2C 1.212(4) . ?
O2C C2C 1.231(4) . ?
C1C C2C 1.500(5) . ?
F1D C1D 1.318(9) . ?
F1E C1E 1.290(12) . ?
F2D C1D 1.256(9) . ?
F2E C1E 1.312(11) . ?
F3D C1D 1.281(8) . ?
F3E C1E 1.293(12) . ?
O1D C2D 1.226(10) . ?
O1E C2E 1.222(12) . ?
O2D C2D 1.205(8) . ?
O2E C2E 1.212(12) . ?
C1D C2D 1.555(10) . ?
C1E C2E 1.563(15) . ?
O1A C9A 1.412(4) . ?
O1A C11A 1.456(4) . ?
N1A C1A 1.137(5) . ?
N2A H2A 0.913(18) . ?
N2A C8A 1.457(4) . ?
N2A C10A 1.479(4) . ?
N3A H3AA 0.887(18) . ?
N3A H3AB 0.949(18) . ?
N3A C14A 1.500(5) . ?
N3A C17A 1.499(5) . ?
C1A C2A 1.447(5) . ?
C2A C3A 1.377(5) . ?
C2A C7A 1.399(5) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.379(5) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.384(4) . ?
C5A C6A 1.392(5) . ?
C5A C8A 1.504(5) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.365(5) . ?
C7A H7A 0.9300 . ?
C8A H8A 0.9800 . ?
C8A C9A 1.515(5) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C10A C11A 1.502(5) . ?
C11A C12A 1.511(5) . ?
C11A C16A 1.533(5) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C12A C13A 1.521(5) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C13A C14A 1.543(5) . ?
C14A H14A 0.9800 . ?
C14A C15A 1.505(5) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C15A C16A 1.514(5) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C17A H17A 0.9800 . ?
C17A C18A 1.509(6) . ?
C17A C19A 1.491(5) . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
O1B C9B 1.432(4) . ?
O1B C11B 1.450(4) . ?
N1B C1B 1.145(5) . ?
N2B H2B 0.905(19) . ?
N2B C8B 1.461(4) . ?
N2B C10B 1.469(4) . ?
N3B H3BA 0.904(18) . ?
N3B H3BB 0.905(18) . ?
N3B C14B 1.494(4) . ?
N3B C17B 1.499(5) . ?
C1B C2B 1.447(6) . ?
C2B C3B 1.380(5) . ?
C2B C7B 1.379(5) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.385(5) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.381(5) . ?
C5B C6B 1.394(5) . ?
C5B C8B 1.512(5) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.393(5) . ?
C7B H7B 0.9300 . ?
C8B H8B 0.9800 . ?
C8B C9B 1.520(5) . ?
C9B H9BA 0.9700 . ?
C9B H9BB 0.9700 . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C10B C11B 1.523(5) . ?
C11B C12B 1.517(5) . ?
C11B C16B 1.529(5) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C12B C13B 1.533(5) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C13B C14B 1.516(5) . ?
C14B H14B 0.9800 . ?
C14B C15B 1.528(5) . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C15B C16B 1.521(5) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C17B H17B 0.9800 . ?
C17B C18B 1.510(5) . ?
C17B C19B 1.514(6) . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1C C1C C2C 109.8(4) . . ?
F2C C1C F1C 106.2(4) . . ?
F2C C1C C2C 113.4(4) . . ?
F3C C1C F1C 105.4(4) . . ?
F3C C1C F2C 106.4(4) . . ?
F3C C1C C2C 115.0(3) . . ?
O1C C2C O2C 128.4(3) . . ?
O1C C2C C1C 117.3(3) . . ?
O2C C2C C1C 114.4(3) . . ?
F1D C1D C2D 108.2(8) . . ?
F2D C1D F1D 111.1(7) . . ?
F2D C1D F3D 105.8(7) . . ?
F2D C1D C2D 113.6(9) . . ?
F3D C1D F1D 102.2(7) . . ?
F3D C1D C2D 115.4(6) . . ?
F1E C1E F2E 105.5(11) . . ?
F1E C1E F3E 103.9(12) . . ?
F1E C1E C2E 121.8(16) . . ?
F2E C1E C2E 112.7(10) . . ?
F3E C1E F2E 101.4(11) . . ?
F3E C1E C2E 109.3(12) . . ?
O1D C2D C1D 111.6(7) . . ?
O2D C2D O1D 133.3(9) . . ?
O2D C2D C1D 114.8(7) . . ?
O1E C2E C1E 114.4(13) . . ?
O2E C2E O1E 130.6(16) . . ?
O2E C2E C1E 115.0(11) . . ?
C9A O1A C11A 113.9(2) . . ?
C8A N2A H2A 106(2) . . ?
C8A N2A C10A 109.8(3) . . ?
C10A N2A H2A 111(2) . . ?
H3AA N3A H3AB 104(2) . . ?
C14A N3A H3AA 105(3) . . ?
C14A N3A H3AB 113(2) . . ?
C17A N3A H3AA 110(3) . . ?
C17A N3A H3AB 106(2) . . ?
C17A N3A C14A 117.9(3) . . ?
N1A C1A C2A 177.9(5) . . ?
C3A C2A C1A 119.5(3) . . ?
C3A C2A C7A 120.1(3) . . ?
C7A C2A C1A 120.4(3) . . ?
C2A C3A H3A 119.8 . . ?
C2A C3A C4A 120.5(3) . . ?
C4A C3A H3A 119.8 . . ?
C3A C4A H4A 119.8 . . ?
C3A C4A C5A 120.4(3) . . ?
C5A C4A H4A 119.8 . . ?
C4A C5A C6A 118.1(3) . . ?
C4A C5A C8A 122.4(3) . . ?
C6A C5A C8A 119.4(3) . . ?
C5A C6A H6A 118.7 . . ?
C7A C6A C5A 122.5(3) . . ?
C7A C6A H6A 118.7 . . ?
C2A C7A H7A 120.8 . . ?
C6A C7A C2A 118.4(3) . . ?
C6A C7A H7A 120.8 . . ?
N2A C8A C5A 113.2(3) . . ?
N2A C8A H8A 108.8 . . ?
N2A C8A C9A 107.4(3) . . ?
C5A C8A H8A 108.8 . . ?
C5A C8A C9A 109.7(3) . . ?
C9A C8A H8A 108.8 . . ?
O1A C9A C8A 112.3(3) . . ?
O1A C9A H9AA 109.1 . . ?
O1A C9A H9AB 109.1 . . ?
C8A C9A H9AA 109.1 . . ?
C8A C9A H9AB 109.1 . . ?
H9AA C9A H9AB 107.9 . . ?
N2A C10A H10A 109.4 . . ?
N2A C10A H10B 109.4 . . ?
N2A C10A C11A 111.2(3) . . ?
H10A C10A H10B 108.0 . . ?
C11A C10A H10A 109.4 . . ?
C11A C10A H10B 109.4 . . ?
O1A C11A C10A 108.8(3) . . ?
O1A C11A C12A 110.5(3) . . ?
O1A C11A C16A 103.2(3) . . ?
C10A C11A C12A 113.7(3) . . ?
C10A C11A C16A 110.7(3) . . ?
C12A C11A C16A 109.4(3) . . ?
C11A C12A H12A 109.1 . . ?
C11A C12A H12B 109.1 . . ?
C11A C12A C13A 112.3(3) . . ?
H12A C12A H12B 107.9 . . ?
C13A C12A H12A 109.1 . . ?
C13A C12A H12B 109.1 . . ?
C12A C13A H13A 109.5 . . ?
C12A C13A H13B 109.5 . . ?
C12A C13A C14A 110.6(3) . . ?
H13A C13A H13B 108.1 . . ?
C14A C13A H13A 109.5 . . ?
C14A C13A H13B 109.5 . . ?
N3A C14A C13A 110.3(3) . . ?
N3A C14A H14A 108.7 . . ?
N3A C14A C15A 109.0(3) . . ?
C13A C14A H14A 108.7 . . ?
C15A C14A C13A 111.3(3) . . ?
C15A C14A H14A 108.7 . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
C14A C15A C16A 110.8(3) . . ?
H15A C15A H15B 108.1 . . ?
C16A C15A H15A 109.5 . . ?
C16A C15A H15B 109.5 . . ?
C11A C16A H16A 109.1 . . ?
C11A C16A H16B 109.1 . . ?
C15A C16A C11A 112.5(3) . . ?
C15A C16A H16A 109.1 . . ?
C15A C16A H16B 109.1 . . ?
H16A C16A H16B 107.8 . . ?
N3A C17A H17A 107.9 . . ?
N3A C17A C18A 108.1(4) . . ?
C18A C17A H17A 107.9 . . ?
C19A C17A N3A 110.7(3) . . ?
C19A C17A H17A 107.9 . . ?
C19A C17A C18A 114.1(4) . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C17A C19A H19A 109.5 . . ?
C17A C19A H19B 109.5 . . ?
C17A C19A H19C 109.5 . . ?
H19A C19A H19B 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C9B O1B C11B 113.3(2) . . ?
C8B N2B H2B 108(2) . . ?
C8B N2B C10B 111.1(3) . . ?
C10B N2B H2B 114(2) . . ?
H3BA N3B H3BB 108(2) . . ?
C14B N3B H3BA 102(2) . . ?
C14B N3B H3BB 109(2) . . ?
C14B N3B C17B 117.1(3) . . ?
C17B N3B H3BA 111(2) . . ?
C17B N3B H3BB 110(2) . . ?
N1B C1B C2B 176.0(4) . . ?
C3B C2B C1B 118.6(4) . . ?
C7B C2B C1B 120.7(3) . . ?
C7B C2B C3B 120.6(3) . . ?
C2B C3B H3B 120.2 . . ?
C2B C3B C4B 119.5(4) . . ?
C4B C3B H3B 120.2 . . ?
C3B C4B H4B 119.4 . . ?
C5B C4B C3B 121.1(3) . . ?
C5B C4B H4B 119.4 . . ?
C4B C5B C6B 118.7(3) . . ?
C4B C5B C8B 120.8(3) . . ?
C6B C5B C8B 120.4(3) . . ?
C5B C6B H6B 119.7 . . ?
C7B C6B C5B 120.5(4) . . ?
C7B C6B H6B 119.7 . . ?
C2B C7B C6B 119.4(3) . . ?
C2B C7B H7B 120.3 . . ?
C6B C7B H7B 120.3 . . ?
N2B C8B C5B 110.5(3) . . ?
N2B C8B H8B 109.8 . . ?
N2B C8B C9B 107.8(3) . . ?
C5B C8B H8B 109.8 . . ?
C5B C8B C9B 109.0(3) . . ?
C9B C8B H8B 109.8 . . ?
O1B C9B C8B 112.7(3) . . ?
O1B C9B H9BA 109.0 . . ?
O1B C9B H9BB 109.0 . . ?
C8B C9B H9BA 109.0 . . ?
C8B C9B H9BB 109.0 . . ?
H9BA C9B H9BB 107.8 . . ?
N2B C10B H10C 109.9 . . ?
N2B C10B H10D 109.9 . . ?
N2B C10B C11B 108.7(3) . . ?
H10C C10B H10D 108.3 . . ?
C11B C10B H10C 109.9 . . ?
C11B C10B H10D 109.9 . . ?
O1B C11B C10B 107.8(3) . . ?
O1B C11B C12B 111.7(3) . . ?
O1B C11B C16B 104.4(3) . . ?
C10B C11B C16B 111.3(3) . . ?
C12B C11B C10B 111.7(3) . . ?
C12B C11B C16B 109.7(3) . . ?
C11B C12B H12C 109.0 . . ?
C11B C12B H12D 109.0 . . ?
C11B C12B C13B 112.9(3) . . ?
H12C C12B H12D 107.8 . . ?
C13B C12B H12C 109.0 . . ?
C13B C12B H12D 109.0 . . ?
C12B C13B H13C 109.7 . . ?
C12B C13B H13D 109.7 . . ?
H13C C13B H13D 108.2 . . ?
C14B C13B C12B 109.8(3) . . ?
C14B C13B H13C 109.7 . . ?
C14B C13B H13D 109.7 . . ?
N3B C14B C13B 111.6(3) . . ?
N3B C14B H14B 108.2 . . ?
N3B C14B C15B 110.2(3) . . ?
C13B C14B H14B 108.2 . . ?
C13B C14B C15B 110.3(3) . . ?
C15B C14B H14B 108.2 . . ?
C14B C15B H15C 109.7 . . ?
C14B C15B H15D 109.7 . . ?
H15C C15B H15D 108.2 . . ?
C16B C15B C14B 109.8(3) . . ?
C16B C15B H15C 109.7 . . ?
C16B C15B H15D 109.7 . . ?
C11B C16B H16C 108.9 . . ?
C11B C16B H16D 108.9 . . ?
C15B C16B C11B 113.2(3) . . ?
C15B C16B H16C 108.9 . . ?
C15B C16B H16D 108.9 . . ?
H16C C16B H16D 107.7 . . ?
N3B C17B H17B 109.1 . . ?
N3B C17B C18B 108.7(3) . . ?
N3B C17B C19B 110.7(4) . . ?
C18B C17B H17B 109.1 . . ?
C18B C17B C19B 110.3(4) . . ?
C19B C17B H17B 109.1 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C17B C19B H19D 109.5 . . ?
C17B C19B H19E 109.5 . . ?
C17B C19B H19F 109.5 . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1C C1C C2C O1C -96.3(4) . . . . ?
F1C C1C C2C O2C 82.8(4) . . . . ?
F2C C1C C2C O1C 22.3(6) . . . . ?
F2C C1C C2C O2C -158.6(4) . . . . ?
F3C C1C C2C O1C 145.1(4) . . . . ?
F3C C1C C2C O2C -35.9(6) . . . . ?
F1D C1D C2D O1D -58.7(14) . . . . ?
F1D C1D C2D O2D 127.0(12) . . . . ?
F1E C1E C2E O1E 37(3) . . . . ?
F1E C1E C2E O2E -142.0(18) . . . . ?
F2D C1D C2D O1D 65.2(13) . . . . ?
F2D C1D C2D O2D -109.2(13) . . . . ?
F2E C1E C2E O1E 164.3(17) . . . . ?
F2E C1E C2E O2E -15(2) . . . . ?
F3D C1D C2D O1D -172.3(10) . . . . ?
F3D C1D C2D O2D 13.3(16) . . . . ?
F3E C1E C2E O1E -84(2) . . . . ?
F3E C1E C2E O2E 97(2) . . . . ?
O1A C11A C12A C13A -57.3(4) . . . . ?
O1A C11A C16A C15A 61.8(4) . . . . ?
N2A C8A C9A O1A 57.9(3) . . . . ?
N2A C10A C11A O1A -54.9(4) . . . . ?
N2A C10A C11A C12A 68.7(4) . . . . ?
N2A C10A C11A C16A -167.7(3) . . . . ?
N3A C14A C15A C16A -177.1(3) . . . . ?
C1A C2A C3A C4A 179.2(3) . . . . ?
C1A C2A C7A C6A -178.1(4) . . . . ?
C2A C3A C4A C5A -0.5(5) . . . . ?
C3A C2A C7A C6A 1.2(6) . . . . ?
C3A C4A C5A C6A -0.2(5) . . . . ?
C3A C4A C5A C8A 176.1(3) . . . . ?
C4A C5A C6A C7A 1.4(6) . . . . ?
C4A C5A C8A N2A 20.5(5) . . . . ?
C4A C5A C8A C9A -99.4(4) . . . . ?
C5A C6A C7A C2A -1.9(6) . . . . ?
C5A C8A C9A O1A -178.7(3) . . . . ?
C6A C5A C8A N2A -163.3(3) . . . . ?
C6A C5A C8A C9A 76.8(4) . . . . ?
C7A C2A C3A C4A 0.0(5) . . . . ?
C8A N2A C10A C11A 60.9(4) . . . . ?
C8A C5A C6A C7A -175.0(4) . . . . ?
C9A O1A C11A C10A 53.2(3) . . . . ?
C9A O1A C11A C12A -72.3(3) . . . . ?
C9A O1A C11A C16A 170.8(3) . . . . ?
C10A N2A C8A C5A 179.1(3) . . . . ?
C10A N2A C8A C9A -59.6(3) . . . . ?
C10A C11A C12A C13A -180.0(3) . . . . ?
C10A C11A C16A C15A 178.0(3) . . . . ?
C11A O1A C9A C8A -56.1(4) . . . . ?
C11A C12A C13A C14A -55.9(4) . . . . ?
C12A C11A C16A C15A -55.9(4) . . . . ?
C12A C13A C14A N3A 176.1(3) . . . . ?
C12A C13A C14A C15A 55.0(4) . . . . ?
C13A C14A C15A C16A -55.2(4) . . . . ?
C14A N3A C17A C18A -162.6(4) . . . . ?
C14A N3A C17A C19A 71.8(4) . . . . ?
C14A C15A C16A C11A 56.4(4) . . . . ?
C16A C11A C12A C13A 55.7(4) . . . . ?
C17A N3A C14A C13A 73.0(4) . . . . ?
C17A N3A C14A C15A -164.5(3) . . . . ?
O1B C11B C12B C13B -62.2(4) . . . . ?
O1B C11B C16B C15B 66.8(4) . . . . ?
N2B C8B C9B O1B 53.6(4) . . . . ?
N2B C10B C11B O1B -59.9(4) . . . . ?
N2B C10B C11B C12B 63.1(4) . . . . ?
N2B C10B C11B C16B -173.8(3) . . . . ?
N3B C14B C15B C16B 177.9(3) . . . . ?
C1B C2B C3B C4B 177.2(3) . . . . ?
C1B C2B C7B C6B -177.1(3) . . . . ?
C2B C3B C4B C5B 0.1(5) . . . . ?
C3B C2B C7B C6B 0.9(5) . . . . ?
C3B C4B C5B C6B 0.4(5) . . . . ?
C3B C4B C5B C8B 177.6(3) . . . . ?
C4B C5B C6B C7B -0.3(5) . . . . ?
C4B C5B C8B N2B 35.9(4) . . . . ?
C4B C5B C8B C9B -82.5(4) . . . . ?
C5B C6B C7B C2B -0.3(5) . . . . ?
C5B C8B C9B O1B 173.7(3) . . . . ?
C6B C5B C8B N2B -147.0(3) . . . . ?
C6B C5B C8B C9B 94.6(4) . . . . ?
C7B C2B C3B C4B -0.7(5) . . . . ?
C8B N2B C10B C11B 63.2(4) . . . . ?
C8B C5B C6B C7B -177.5(3) . . . . ?
C9B O1B C11B C10B 57.1(3) . . . . ?
C9B O1B C11B C12B -65.9(3) . . . . ?
C9B O1B C11B C16B 175.6(3) . . . . ?
C10B N2B C8B C5B -177.3(3) . . . . ?
C10B N2B C8B C9B -58.2(4) . . . . ?
C10B C11B C12B C13B 177.0(3) . . . . ?
C10B C11B C16B C15B -177.2(3) . . . . ?
C11B O1B C9B C8B -55.4(4) . . . . ?
C11B C12B C13B C14B -56.9(4) . . . . ?
C12B C11B C16B C15B -53.1(4) . . . . ?
C12B C13B C14B N3B -178.5(3) . . . . ?
C12B C13B C14B C15B 58.6(4) . . . . ?
C13B C14B C15B C16B -58.4(4) . . . . ?
C14B N3B C17B C18B -174.1(3) . . . . ?
C14B N3B C17B C19B 64.6(4) . . . . ?
C14B C15B C16B C11B 56.2(4) . . . . ?
C16B C11B C12B C13B 53.1(4) . . . . ?
C17B N3B C14B C13B 67.5(4) . . . . ?
C17B N3B C14B C15B -169.6(3) . . . . ?

_olex2_date_sample_data_collection 2020-09-23
_olex2_date_sample_submission    2020-09-23
_olex2_submission_original_sample_id jb230920_1_1
_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 1.495
_oxdiff_exptl_absorpt_empirical_full_min 0.765
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_jb241020_2_1
_database_code_depnum_ccdc_archive 'CCDC 2064034'
loop_
_audit_author_name
_audit_author_address
'Nils Trapp'
;ETH Small Molecule Crystallography Center
Switzerland
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-04-09 downloaded from the CCDC.
;
_audit_creation_date             2020-10-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
angus.mcmillan@org.chem.ethz.ch
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 F3 O2, C19 H28 N3 O'
_chemical_formula_sum            'C21 H28 F3 N3 O3'
_chemical_formula_weight         427.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H28F3N3O3
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'
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      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                   8.7250(3)
_cell_length_b                   11.2299(6)
_cell_length_c                   12.2001(5)
_cell_angle_alpha                79.147(4)
_cell_angle_beta                 80.009(3)
_cell_angle_gamma                73.949(4)
_cell_volume                     1118.85(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5118
_cell_measurement_temperature    250.0(1)
_cell_measurement_theta_max      74.8440
_cell_measurement_theta_min      3.7240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             452
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0103
0 1 0 0.0130
0 0 1 0.0074
0 0 -1 0.0210
4 2 7 0.0419
-4 -2 -6 0.0522
4 -4 2 0.0497
-4 3 0 0.0577
0 -5 -6 0.0186
-4 -6 2 0.0455
3 7 -1 0.0505
-3 3 -4 0.0454

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.023
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
-0.0000 -1.0000 -0.0000 -0.0067 -0.1422 -0.0239
0.0000 1.0000 0.0000 0.0067 0.1422 0.0239
-0.0000 -0.0000 1.0000 -0.0648 0.0024 -0.1123
0.0000 0.0000 -1.0000 0.0648 -0.0024 0.1123
3.7327 1.5928 6.7425 -0.9470 0.0234 -0.3205
-4.0849 -1.7499 -6.3723 0.9711 -0.0241 0.2376
3.6754 -3.6201 2.3130 -0.6870 -0.7252 0.0463
-4.3719 2.8909 -0.0611 0.6335 0.6678 -0.3909
-0.2190 -5.1447 -6.2074 0.3981 -0.7336 0.5508
-3.5036 -5.8787 1.6589 0.3420 -0.6261 -0.7007
2.9380 6.6362 -0.7290 -0.3182 0.7693 0.5540
-3.4828 3.1567 -3.8023 0.7535 0.6444 0.1304

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17567
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.627
_diffrn_reflns_theta_min         3.720
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  18.00   0.50    7.00    --  -48.62  77.00 150.00  180
  2  ω    -38.00   6.00   0.50   17.80    --  -70.00  38.00 120.00   88
  3  ω    -38.00   6.00   0.50   17.80    --  -70.00  38.00  60.00   88
  4  ω    -38.00   6.00   0.50   17.80    --  -70.00  38.00 -30.00   88
  5  ω    -38.00   6.00   0.50   17.80    --  -70.00  38.00 -90.00   88
  6  ω    -38.00   6.00   0.50   17.80    --  -70.00  38.00-180.00   88
  7  ω    -68.00   2.00   0.50   17.80    --  -70.00  57.00 -30.00  140
  8  ω   -115.00 -25.00   0.50    7.00    --  -48.62 -77.00  30.00  180
  9  ω   -115.00 -74.00   0.50    7.00    --  -48.62 -77.00 120.00   82
 10  ω   -115.00 -25.00   0.50    7.00    --  -48.62 -77.00 -60.00  180
 11  ω    -27.00   9.00   0.50    7.00    --   48.62 -19.00 -60.00   72
 12  ω     45.00 134.00   0.50   17.80    --  110.00 -77.00  60.00  178
 13  ω     97.00 176.00   0.50   17.80    --  110.00  19.00 120.00  158
 14  ω     94.00 178.00   0.50   17.80    --  110.00  57.00 150.00  168
 15  ω     86.00 176.00   0.50   17.80    --  110.00  77.00  60.00  180
 16  ω     94.00 178.00   0.50   17.80    --  110.00 125.00 120.00  168
 17  ω     98.00 178.00   0.50   17.80    --  110.00  38.00-120.00  160
 18  ω     98.00 178.00   0.50   17.80    --  110.00  38.00-150.00  160
 19  ω     38.00  68.00   0.50   17.80    --  110.00 -57.00   0.00   60
 20  ω     38.00  68.00   0.50   17.80    --  110.00 -57.00 -60.00   60
 21  ω     38.00  68.00   0.50   17.80    --  110.00 -57.00 -90.00   60
 22  ω     38.00  68.00   0.50   17.80    --  110.00 -57.00-150.00   60
 23  ω     38.00  68.00   0.50   17.80    --  110.00 -57.00-120.00   60
 24  ω     40.00 106.00   0.50   17.80    --  110.00 -99.00 -90.00  132
 25  ω     60.00 121.00   0.50    7.00    --   48.62-178.00-150.00  122
 26  ω     39.00 113.00   0.50   17.80    --  110.00-125.00   0.00  148
 27  ω     40.00 106.00   0.50   17.80    --  110.00 -99.00 120.00  132
 28  ω     39.00 113.00   0.50   17.80    --  110.00-125.00  90.00  148
 29  ω     38.00  68.00   0.50   17.80    --  110.00 -57.00  90.00   60
 30  ω     38.00  68.00   0.50   17.80    --  110.00 -57.00 150.00   60
 31  ω     38.00  68.00   0.50   17.80    --  110.00 -57.00  30.00   60
 32  ω     40.00 106.00   0.50   17.80    --  110.00 -99.00 -30.00  132
 33  ω     39.00 113.00   0.50   17.80    --  110.00-125.00 -90.00  148
 34  ω     39.00 113.00   0.50   17.80    --  110.00-125.00-120.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1395503000
_diffrn_orient_matrix_UB_12      0.0067125000
_diffrn_orient_matrix_UB_13      -0.0647744000
_diffrn_orient_matrix_UB_21      -0.0587458000
_diffrn_orient_matrix_UB_22      0.1421988000
_diffrn_orient_matrix_UB_23      0.0023938000
_diffrn_orient_matrix_UB_31      0.1067715000
_diffrn_orient_matrix_UB_32      0.0238715000
_diffrn_orient_matrix_UB_33      -0.1122856000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2915
_reflns_number_total             4740
_reflns_odcompleteness_completeness 99.98
_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.
 
 _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 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_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 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         4740
_refine_ls_number_restraints     688
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.049
_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)+(0.0843P)²+0.0797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1412
_refine_ls_wR_factor_ref         0.1644
_refine_special_details          
'Crystals crack into powder upon further cooling. Full molecule disorder.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2 = N2A-H2AD
 0.93 with sigma of 0.01
 F1-C21 \\sim F2A-C21A \\sim F1A-C21A \\sim F2-C21 \\sim F3A-C21A \\sim F3-C21
 with sigma of 0.02
 C14-C13 \\sim C15A-C14A \\sim C14A-C13A \\sim C18-C13 \\sim C16A-C15A \\sim
C15-C14 \\sim C18A-C13A ~
 C18-C17 \\sim C18A-C17A \\sim C16-C15 \\sim C17A-C16A \\sim C17-C16
 with sigma of 0.02
 C19-C16 \\sim C19A-C16A
 with sigma of 0.02
 N1-C1 \\sim N1A-C1A
 with sigma of 0.02
 N3-C19 \\sim N3A-C19A
 with sigma of 0.02
 C16-N3 \\sim C16A-N3A
 with sigma of 0.02
 N1-C4 \\sim N1A-C4A
 with sigma of 0.02
 C14-C17 \\sim C15-C18 \\sim C14A-C17A \\sim C15A-C18A
 with sigma of 0.02
 C13-C16 \\sim C13A-C16A
 with sigma of 0.02
 O2-O3 \\sim O2A-O3A
 with sigma of 0.02
 C21A-C20A \\sim C21-C20
 with sigma of 0.02
 F1-F2 \\sim F2-F3 \\sim F3-F1 \\sim F1A-F2A \\sim F2A-F3A \\sim F3A-F1A
 with sigma of 0.02
 C13-C12 \\sim C13A-C12A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C3-C1 \\sim C3A-C1A \\sim C2A-C1A \\sim C2-C1
 with sigma of 0.02
 O2-C20 \\sim O2A-C20A \\sim O3A-C20A \\sim O3-C20
 with sigma of 0.02
 C20-F1 \\sim C20-F2 \\sim C20-F3 \\sim C20A-F1A \\sim C20A-F2A \\sim C20A-F3A
 with sigma of 0.02
 O2-C21 \\sim O2A-C21A \\sim O3-C21 \\sim O3A-C21A
 with sigma of 0.02
 C7-C6 \\sim C5-C4 \\sim C9A-C8A \\sim C8-C7 \\sim C9A-C4A \\sim C8A-C7A \\sim
C6A-C5A \\sim C7A-C6A \\sim C9-
 C4 \\sim C6-C5 \\sim C5A-C4A \\sim C9-C8
 with sigma of 0.02
 C1-C4 \\sim C1A-C4A
 with sigma of 0.02
 O1A-C7A \\sim O1-C7
 with sigma of 0.02
 C12-C11 \\sim C12A-C11A
 with sigma of 0.02
 C7-C10 \\sim C7A-C10A
 with sigma of 0.02
 N2-C10 \\sim N2A-C10A \\sim N2-C12 \\sim N2A-C12A
 with sigma of 0.02
 O1-C11 \\sim O1A-C11A
 with sigma of 0.02
 N2-O1 \\sim N2A-O1A
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
3. Restrained planarity
 C13, C14, C15, C16, C17, C18, C19, C12, N3
 with sigma of 0.1
 C12A, C13A, C14A, C15A, C16A, C17A, C18A, C19A, N3A
 with sigma of 0.1
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(C21A)=Sof(C20A)=Sof(O2A)=Sof(O3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(O2)=Sof(O3)=Sof(C20)=Sof(C21)=FVAR(1)
 Sof(C4A)=Sof(H4A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=
 Sof(C7A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C3A)=
 Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C1A)=Sof(H1AA)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 Sof(H2AC)=Sof(N1A)=Sof(H1AB)=Sof(H1AC)=Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(N2A)=
 Sof(H2AD)=Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(O1A)=Sof(C13A)=
 Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(N3A)=1-FVAR(2)
 Sof(O1)=Sof(N1)=Sof(H1A)=Sof(H1B)=Sof(N2)=Sof(H2)=Sof(N3)=Sof(C1)=Sof(H1)=
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C4)=
 Sof(H4)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C7)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C12(H12), C4A(H4A), C1A(H1AA), C12A(H12A)
6.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C9A(H9AA,H9AB), C8A(H8AA,H8AB), C6A(H6AA,H6AB),
 C5A(H5AA,H5AB), N1A(H1AB,H1AC), C10A(H10C,H10D), C11A(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18), C14A(H14A), C15A(H15A), C17A(H17A),
 C18A(H18A)
6.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC), C2A(H2AA,H2AB,H2AC)
;
_atom_sites_solution_hydrogens   mixed
_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
F1 F 0.5419(5) 0.8690(3) -0.0716(3) 0.1373(18) Uani 0.495(6) 1 d D . P A 1
F2 F 0.5152(9) 0.8343(8) 0.1098(7) 0.214(4) Uani 0.495(6) 1 d D . P A 1
F3 F 0.7062(8) 0.8958(6) 0.0277(9) 0.183(4) Uani 0.495(6) 1 d D . P A 1
O2 O 0.6331(8) 0.6206(5) -0.0068(7) 0.0801(14) Uani 0.495(6) 1 d D . P A 1
O3 O 0.8381(8) 0.6465(8) 0.0551(7) 0.144(3) Uani 0.495(6) 1 d D . P A 1
C20 C 0.7082(9) 0.6886(6) 0.0187(10) 0.071(3) Uani 0.495(6) 1 d D . P A 1
C21 C 0.6201(8) 0.8238(5) 0.0142(6) 0.0815(16) Uani 0.495(6) 1 d D . P A 1
O1 O 0.2415(3) 0.3745(3) 0.5051(3) 0.1155(11) Uani 0.742(4) 1 d D . P B 1
N1 N 0.1600(9) 0.6028(6) 0.0583(4) 0.0639(10) Uani 0.742(4) 1 d D . P B 1
H1A H 0.057715 0.620693 0.046440 0.077 Uiso 0.742(4) 1 calc R U P B 1
H1B H 0.209652 0.531044 0.032407 0.077 Uiso 0.742(4) 1 calc R U P B 1
N2 N 0.5020(5) 0.2239(6) 0.3887(5) 0.0769(10) Uani 0.742(4) 1 d D . P B 1
H2 H 0.581(4) 0.170(3) 0.348(3) 0.092 Uiso 0.742(4) 1 d D U P B 1
N3 N 1.2170(7) 0.0124(7) 0.7115(7) 0.0991(14) Uani 0.742(4) 1 d D . P B 1
C1 C 0.2325(13) 0.7030(5) -0.0121(6) 0.0721(15) Uani 0.742(4) 1 d D . P B 1
H1 H 0.347029 0.684445 -0.004398 0.087 Uiso 0.742(4) 1 calc R U P B 1
C2 C 0.2116(13) 0.6982(11) -0.1329(7) 0.109(2) Uani 0.742(4) 1 d D . P B 1
H2A H 0.261958 0.615560 -0.151026 0.163 Uiso 0.742(4) 1 calc R U P B 1
H2B H 0.260491 0.757696 -0.183653 0.163 Uiso 0.742(4) 1 calc R U P B 1
H2C H 0.099024 0.718429 -0.139994 0.163 Uiso 0.742(4) 1 calc R U P B 1
C3 C 0.1444(6) 0.8292(5) 0.0241(6) 0.0869(14) Uani 0.742(4) 1 d D . P B 1
H3A H 0.032086 0.845606 0.017755 0.130 Uiso 0.742(4) 1 calc R U P B 1
H3B H 0.187784 0.893772 -0.023433 0.130 Uiso 0.742(4) 1 calc R U P B 1
H3C H 0.157741 0.828072 0.100780 0.130 Uiso 0.742(4) 1 calc R U P B 1
C4 C 0.1631(4) 0.5802(3) 0.1826(4) 0.0701(9) Uani 0.742(4) 1 d D . P B 1
H4 H 0.104452 0.656855 0.213918 0.084 Uiso 0.742(4) 1 calc R U P B 1
C5 C 0.3352(3) 0.5427(3) 0.2101(3) 0.0763(7) Uani 0.742(4) 1 d D . P B 1
H5A H 0.382692 0.613420 0.185246 0.092 Uiso 0.742(4) 1 calc R U P B 1
H5B H 0.397703 0.475070 0.169317 0.092 Uiso 0.742(4) 1 calc R U P B 1
C6 C 0.3431(3) 0.5005(2) 0.3363(2) 0.0864(8) Uani 0.742(4) 1 d D . P B 1
H6A H 0.454859 0.471099 0.349160 0.104 Uiso 0.742(4) 1 calc R U P B 1
H6B H 0.293985 0.571822 0.375733 0.104 Uiso 0.742(4) 1 calc R U P B 1
C7 C 0.2583(4) 0.3965(4) 0.3847(4) 0.0822(10) Uani 0.742(4) 1 d D . P B 1
C8 C 0.0871(3) 0.4378(3) 0.3552(3) 0.0991(10) Uani 0.742(4) 1 d D . P B 1
H8A H 0.035919 0.369395 0.381970 0.119 Uiso 0.742(4) 1 calc R U P B 1
H8B H 0.027376 0.507470 0.394356 0.119 Uiso 0.742(4) 1 calc R U P B 1
C9 C 0.0769(4) 0.4771(3) 0.2305(3) 0.0841(8) Uani 0.742(4) 1 d D . P B 1
H9A H -0.035138 0.507058 0.218116 0.101 Uiso 0.742(4) 1 calc R U P B 1
H9B H 0.125120 0.405327 0.191503 0.101 Uiso 0.742(4) 1 calc R U P B 1
C10 C 0.3481(5) 0.2737(4) 0.3435(4) 0.0808(9) Uani 0.742(4) 1 d D . P B 1
H10A H 0.283199 0.213506 0.366984 0.097 Uiso 0.742(4) 1 calc R U P B 1
H10B H 0.367081 0.286748 0.261893 0.097 Uiso 0.742(4) 1 calc R U P B 1
C11 C 0.3893(6) 0.3248(6) 0.5507(3) 0.1063(14) Uani 0.742(4) 1 d D . P B 1
H11A H 0.367735 0.312288 0.632171 0.128 Uiso 0.742(4) 1 calc R U P B 1
H11B H 0.454521 0.384793 0.528380 0.128 Uiso 0.742(4) 1 calc R U P B 1
C12 C 0.4826(9) 0.2011(7) 0.5114(5) 0.0812(15) Uani 0.742(4) 1 d D . P B 1
H12 H 0.419494 0.138973 0.538208 0.097 Uiso 0.742(4) 1 calc R U P B 1
C13 C 0.6415(7) 0.1547(5) 0.5584(5) 0.0662(13) Uani 0.742(4) 1 d D . P B 1
C14 C 0.6574(7) 0.0760(6) 0.6591(5) 0.0766(12) Uani 0.742(4) 1 d D . P B 1
H14 H 0.569426 0.047862 0.697939 0.092 Uiso 0.742(4) 1 calc R U P B 1
C15 C 0.8014(7) 0.0379(6) 0.7038(5) 0.0800(11) Uani 0.742(4) 1 d D . P B 1
H15 H 0.809193 -0.015101 0.772149 0.096 Uiso 0.742(4) 1 calc R U P B 1
C16 C 0.9329(8) 0.0781(6) 0.6478(6) 0.0684(13) Uani 0.742(4) 1 d D . P B 1
C17 C 0.9173(8) 0.1586(10) 0.5486(7) 0.0837(16) Uani 0.742(4) 1 d D . P B 1
H17 H 1.003727 0.190016 0.511705 0.100 Uiso 0.742(4) 1 calc R U P B 1
C18 C 0.7757(9) 0.1934(6) 0.5032(6) 0.0878(14) Uani 0.742(4) 1 d D . P B 1
H18 H 0.769690 0.244150 0.433657 0.105 Uiso 0.742(4) 1 calc R U P B 1
C19 C 1.0878(11) 0.0386(7) 0.6872(10) 0.0811(16) Uani 0.742(4) 1 d D . P B 1
F1A F 0.6911(10) 0.8917(6) -0.0265(8) 0.224(5) Uani 0.505(6) 1 d D . P A 2
F2A F 0.4911(4) 0.8409(3) 0.0797(6) 0.128(2) Uani 0.505(6) 1 d D . P A 2
F3A F 0.7185(8) 0.8108(10) 0.1423(6) 0.257(4) Uani 0.505(6) 1 d D . P A 2
C21A C 0.6474(8) 0.8081(8) 0.0594(7) 0.113(3) Uani 0.505(6) 1 d D . P A 2
C20A C 0.7163(10) 0.6803(7) 0.0236(10) 0.077(3) Uani 0.505(6) 1 d D . P A 2
O2A O 0.8614(7) 0.6583(9) -0.0005(5) 0.132(3) Uani 0.505(6) 1 d D . P A 2
O3A O 0.6257(10) 0.6295(8) 0.0075(10) 0.142(4) Uani 0.505(6) 1 d D . P A 2
C4A C 0.1303(12) 0.6150(11) 0.2141(10) 0.080(3) Uani 0.258(4) 1 d D . P B 2
H4A H 0.068369 0.700032 0.225226 0.096 Uiso 0.258(4) 1 calc R U P B 2
C9A C 0.2916(10) 0.5901(8) 0.2568(8) 0.079(2) Uani 0.258(4) 1 d D . P B 2
H9AA H 0.354521 0.643105 0.208351 0.095 Uiso 0.258(4) 1 calc R U P B 2
H9AB H 0.273670 0.612318 0.331879 0.095 Uiso 0.258(4) 1 calc R U P B 2
C8A C 0.3858(7) 0.4548(6) 0.2601(6) 0.0665(18) Uani 0.258(4) 1 d D . P B 2
H8AA H 0.483421 0.442962 0.293063 0.080 Uiso 0.258(4) 1 calc R U P B 2
H8AB H 0.416802 0.436023 0.183713 0.080 Uiso 0.258(4) 1 calc R U P B 2
C7A C 0.2904(9) 0.3628(9) 0.3280(8) 0.0702(19) Uani 0.258(4) 1 d D . P B 2
C6A C 0.1303(8) 0.3874(8) 0.2820(8) 0.086(2) Uani 0.258(4) 1 d D . P B 2
H6AA H 0.150680 0.365069 0.206847 0.103 Uiso 0.258(4) 1 calc R U P B 2
H6AB H 0.065817 0.334828 0.329382 0.103 Uiso 0.258(4) 1 calc R U P B 2
C5A C 0.0370(10) 0.5246(9) 0.2781(8) 0.092(3) Uani 0.258(4) 1 d D . P B 2
H5AA H -0.059697 0.537183 0.243787 0.111 Uiso 0.258(4) 1 calc R U P B 2
H5AB H 0.004158 0.542974 0.354486 0.111 Uiso 0.258(4) 1 calc R U P B 2
C3A C 0.130(3) 0.842(2) 0.031(3) 0.156(10) Uani 0.258(4) 1 d D . P B 2
H3AA H 0.175503 0.862958 0.088916 0.234 Uiso 0.258(4) 1 calc R U P B 2
H3AB H 0.017403 0.848527 0.054381 0.234 Uiso 0.258(4) 1 calc R U P B 2
H3AC H 0.144240 0.897807 -0.037276 0.234 Uiso 0.258(4) 1 calc R U P B 2
C1A C 0.215(4) 0.7070(19) 0.0119(16) 0.076(4) Uani 0.258(4) 1 d D . P B 2
H1AA H 0.324831 0.695025 0.027415 0.091 Uiso 0.258(4) 1 calc R U P B 2
C2A C 0.233(3) 0.691(3) -0.112(2) 0.094(5) Uani 0.258(4) 1 d D . P B 2
H2AA H 0.131374 0.726748 -0.139793 0.141 Uiso 0.258(4) 1 calc R U P B 2
H2AB H 0.267629 0.603600 -0.118192 0.141 Uiso 0.258(4) 1 calc R U P B 2
H2AC H 0.311169 0.733047 -0.154260 0.141 Uiso 0.258(4) 1 calc R U P B 2
N1A N 0.153(3) 0.6066(18) 0.0933(11) 0.065(3) Uani 0.258(4) 1 d D . P B 2
H1AB H 0.059635 0.605516 0.074733 0.078 Uiso 0.258(4) 1 calc R U P B 2
H1AC H 0.221631 0.533200 0.082825 0.078 Uiso 0.258(4) 1 calc R U P B 2
C10A C 0.3839(13) 0.2321(11) 0.3123(9) 0.079(2) Uani 0.258(4) 1 d D . P B 2
H10C H 0.320472 0.173505 0.348534 0.095 Uiso 0.258(4) 1 calc R U P B 2
H10D H 0.406912 0.225395 0.232712 0.095 Uiso 0.258(4) 1 calc R U P B 2
N2A N 0.5352(13) 0.2006(17) 0.3612(11) 0.077(3) Uani 0.258(4) 1 d D . P B 2
H2AD H 0.574(10) 0.114(2) 0.367(7) 0.093 Uiso 0.258(4) 1 d D U P B 2
C12A C 0.495(2) 0.1991(16) 0.4818(14) 0.064(3) Uani 0.258(4) 1 d D . P B 2
H12A H 0.435755 0.135367 0.514747 0.077 Uiso 0.258(4) 1 calc R U P B 2
C11A C 0.3935(14) 0.3292(13) 0.5030(10) 0.089(3) Uani 0.258(4) 1 d D . P B 2
H11C H 0.359151 0.328148 0.583143 0.107 Uiso 0.258(4) 1 calc R U P B 2
H11D H 0.459092 0.388824 0.478869 0.107 Uiso 0.258(4) 1 calc R U P B 2
O1A O 0.2566(8) 0.3688(9) 0.4453(9) 0.089(2) Uani 0.258(4) 1 d D . P B 2
C13A C 0.6514(18) 0.1698(13) 0.5281(12) 0.057(3) Uani 0.258(4) 1 d D . P B 2
C14A C 0.666(2) 0.0930(19) 0.6287(14) 0.076(4) Uani 0.258(4) 1 d D . P B 2
H14A H 0.579046 0.062960 0.666376 0.091 Uiso 0.258(4) 1 calc R U P B 2
C15A C 0.809(2) 0.0587(19) 0.6758(13) 0.087(4) Uani 0.258(4) 1 d D . P B 2
H15A H 0.817880 0.003103 0.742639 0.105 Uiso 0.258(4) 1 calc R U P B 2
C16A C 0.936(2) 0.1058(18) 0.6248(17) 0.060(3) Uani 0.258(4) 1 d D . P B 2
C17A C 0.923(2) 0.181(3) 0.5231(19) 0.071(3) Uani 0.258(4) 1 d D . P B 2
H17A H 1.011775 0.206844 0.482769 0.085 Uiso 0.258(4) 1 calc R U P B 2
C18A C 0.7785(19) 0.2194(15) 0.4804(12) 0.061(2) Uani 0.258(4) 1 d D . P B 2
H18A H 0.766763 0.280605 0.417339 0.073 Uiso 0.258(4) 1 calc R U P B 2
C19A C 1.079(3) 0.0727(19) 0.680(3) 0.080(4) Uani 0.258(4) 1 d D . P B 2
N3A N 1.183(2) 0.032(3) 0.7333(19) 0.118(7) Uani 0.258(4) 1 d D . P B 2


_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
F1 C21 1.294(7) . ?
F2 C21 1.354(8) . ?
F3 C21 1.294(7) . ?
O2 C20 1.243(7) . ?
O3 C20 1.226(9) . ?
C20 C21 1.496(8) . ?
O1 C7 1.431(4) . ?
O1 C11 1.420(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.499(5) . ?
N1 C4 1.494(4) . ?
N2 H2 0.921(10) . ?
N2 C10 1.465(5) . ?
N2 C12 1.459(5) . ?
N3 C19 1.160(6) . ?
C1 H1 0.9800 . ?
C1 C2 1.529(6) . ?
C1 C3 1.520(6) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9800 . ?
C4 C5 1.522(4) . ?
C4 C9 1.524(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.531(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.525(5) . ?
C7 C8 1.522(5) . ?
C7 C10 1.515(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.513(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.521(6) . ?
C12 H12 0.9800 . ?
C12 C13 1.512(6) . ?
C13 C14 1.375(5) . ?
C13 C18 1.382(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(5) . ?
C16 C17 1.371(5) . ?
C16 C19 1.438(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(6) . ?
C18 H18 0.9300 . ?
F1A C21A 1.347(9) . ?
F2A C21A 1.302(8) . ?
F3A C21A 1.284(8) . ?
C21A C20A 1.510(8) . ?
C20A O2A 1.215(9) . ?
C20A O3A 1.156(9) . ?
C4A H4A 0.9800 . ?
C4A C9A 1.521(11) . ?
C4A C5A 1.497(11) . ?
C4A N1A 1.470(11) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C8A 1.511(9) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C7A 1.537(8) . ?
C7A C6A 1.530(9) . ?
C7A C10A 1.498(11) . ?
C7A O1A 1.420(10) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C6A C5A 1.527(11) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C3A C1A 1.530(14) . ?
C1A H1AA 0.9800 . ?
C1A C2A 1.525(13) . ?
C1A N1A 1.507(14) . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
N1A H1AB 0.8900 . ?
N1A H1AC 0.8900 . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A N2A 1.470(13) . ?
N2A H2AD 0.928(11) . ?
N2A C12A 1.450(11) . ?
C12A H12A 0.9800 . ?
C12A C11A 1.528(14) . ?
C12A C13A 1.500(15) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A O1A 1.415(12) . ?
C13A C14A 1.364(10) . ?
C13A C18A 1.368(12) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.389(13) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.364(12) . ?
C16A C17A 1.367(10) . ?
C16A C19A 1.438(13) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.373(13) . ?
C18A H18A 0.9300 . ?
C19A N3A 1.152(14) . ?

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
O2 C20 C21 115.0(6) . . ?
O3 C20 O2 122.5(7) . . ?
O3 C20 C21 122.1(7) . . ?
F1 C21 F2 109.0(6) . . ?
F1 C21 F3 111.8(6) . . ?
F1 C21 C20 114.5(6) . . ?
F2 C21 C20 107.0(7) . . ?
F3 C21 F2 99.0(6) . . ?
F3 C21 C20 114.3(6) . . ?
C11 O1 C7 114.2(3) . . ?
H1A N1 H1B 107.0 . . ?
C1 N1 H1A 107.6 . . ?
C1 N1 H1B 107.6 . . ?
C4 N1 H1A 107.6 . . ?
C4 N1 H1B 107.6 . . ?
C4 N1 C1 118.9(4) . . ?
C10 N2 H2 117(3) . . ?
C12 N2 H2 120(3) . . ?
C12 N2 C10 112.6(4) . . ?
N1 C1 H1 110.2 . . ?
N1 C1 C2 104.8(7) . . ?
N1 C1 C3 109.6(6) . . ?
C2 C1 H1 110.2 . . ?
C3 C1 H1 110.2 . . ?
C3 C1 C2 111.8(5) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4 109.3 . . ?
N1 C4 C5 110.8(4) . . ?
N1 C4 C9 106.5(3) . . ?
C5 C4 H4 109.3 . . ?
C5 C4 C9 111.5(3) . . ?
C9 C4 H4 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 C6 111.8(3) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.8(3) . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
O1 C7 C6 111.7(4) . . ?
O1 C7 C8 105.1(3) . . ?
O1 C7 C10 107.6(3) . . ?
C8 C7 C6 109.1(3) . . ?
C10 C7 C6 112.0(3) . . ?
C10 C7 C8 111.0(4) . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 C7 113.8(3) . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C4 C9 H9A 109.4 . . ?
C4 C9 H9B 109.4 . . ?
C8 C9 C4 111.0(3) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C7 110.6(3) . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O1 C11 H11A 109.2 . . ?
O1 C11 H11B 109.2 . . ?
O1 C11 C12 112.2(5) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
N2 C12 C11 106.6(4) . . ?
N2 C12 H12 109.1 . . ?
N2 C12 C13 112.8(6) . . ?
C11 C12 H12 109.1 . . ?
C13 C12 C11 110.1(5) . . ?
C13 C12 H12 109.1 . . ?
C14 C13 C12 121.7(5) . . ?
C14 C13 C18 117.3(4) . . ?
C18 C13 C12 121.0(6) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(4) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C19 123.3(6) . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 C19 118.0(6) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.2 . . ?
C17 C18 C13 121.5(4) . . ?
C17 C18 H18 119.2 . . ?
N3 C19 C16 174.6(11) . . ?
F1A C21A C20A 106.8(7) . . ?
F2A C21A F1A 107.1(7) . . ?
F2A C21A C20A 114.7(6) . . ?
F3A C21A F1A 106.9(7) . . ?
F3A C21A F2A 113.7(7) . . ?
F3A C21A C20A 107.1(7) . . ?
O2A C20A C21A 111.6(7) . . ?
O3A C20A C21A 116.9(7) . . ?
O3A C20A O2A 130.4(9) . . ?
C9A C4A H4A 108.5 . . ?
C5A C4A H4A 108.5 . . ?
C5A C4A C9A 110.9(9) . . ?
N1A C4A H4A 108.5 . . ?
N1A C4A C9A 110.5(11) . . ?
N1A C4A C5A 110.0(11) . . ?
C4A C9A H9AA 109.1 . . ?
C4A C9A H9AB 109.1 . . ?
H9AA C9A H9AB 107.8 . . ?
C8A C9A C4A 112.6(7) . . ?
C8A C9A H9AA 109.1 . . ?
C8A C9A H9AB 109.1 . . ?
C9A C8A H8AA 109.0 . . ?
C9A C8A H8AB 109.0 . . ?
C9A C8A C7A 112.8(6) . . ?
H8AA C8A H8AB 107.8 . . ?
C7A C8A H8AA 109.0 . . ?
C7A C8A H8AB 109.0 . . ?
C6A C7A C8A 109.4(6) . . ?
C10A C7A C8A 108.7(8) . . ?
C10A C7A C6A 107.7(8) . . ?
O1A C7A C8A 114.7(8) . . ?
O1A C7A C6A 108.0(7) . . ?
O1A C7A C10A 108.2(6) . . ?
C7A C6A H6AA 109.3 . . ?
C7A C6A H6AB 109.3 . . ?
H6AA C6A H6AB 108.0 . . ?
C5A C6A C7A 111.5(7) . . ?
C5A C6A H6AA 109.3 . . ?
C5A C6A H6AB 109.3 . . ?
C4A C5A C6A 113.9(7) . . ?
C4A C5A H5AA 108.8 . . ?
C4A C5A H5AB 108.8 . . ?
C6A C5A H5AA 108.8 . . ?
C6A C5A H5AB 108.8 . . ?
H5AA C5A H5AB 107.7 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C1A C3A H3AA 109.5 . . ?
C1A C3A H3AB 109.5 . . ?
C1A C3A H3AC 109.5 . . ?
C3A C1A H1AA 104.5 . . ?
C2A C1A C3A 112.1(14) . . ?
C2A C1A H1AA 104.5 . . ?
N1A C1A C3A 115.3(19) . . ?
N1A C1A H1AA 104.5 . . ?
N1A C1A C2A 114(2) . . ?
C1A C2A H2AA 109.5 . . ?
C1A C2A H2AB 109.5 . . ?
C1A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C4A N1A C1A 118.2(12) . . ?
C4A N1A H1AB 107.8 . . ?
C4A N1A H1AC 107.8 . . ?
C1A N1A H1AB 107.8 . . ?
C1A N1A H1AC 107.8 . . ?
H1AB N1A H1AC 107.1 . . ?
C7A C10A H10C 109.6 . . ?
C7A C10A H10D 109.6 . . ?
H10C C10A H10D 108.2 . . ?
N2A C10A C7A 110.1(9) . . ?
N2A C10A H10C 109.6 . . ?
N2A C10A H10D 109.6 . . ?
C10A N2A H2AD 106(6) . . ?
C12A N2A C10A 107.6(11) . . ?
C12A N2A H2AD 94(5) . . ?
N2A C12A H12A 110.7 . . ?
N2A C12A C11A 108.2(11) . . ?
N2A C12A C13A 106.0(13) . . ?
C11A C12A H12A 110.7 . . ?
C13A C12A H12A 110.7 . . ?
C13A C12A C11A 110.2(10) . . ?
C12A C11A H11C 109.2 . . ?
C12A C11A H11D 109.2 . . ?
H11C C11A H11D 107.9 . . ?
O1A C11A C12A 112.0(10) . . ?
O1A C11A H11C 109.2 . . ?
O1A C11A H11D 109.2 . . ?
C11A O1A C7A 114.5(7) . . ?
C14A C13A C12A 117.7(14) . . ?
C14A C13A C18A 117.1(11) . . ?
C18A C13A C12A 125.1(14) . . ?
C13A C14A H14A 119.4 . . ?
C13A C14A C15A 121.2(11) . . ?
C15A C14A H14A 119.4 . . ?
C14A C15A H15A 119.7 . . ?
C16A C15A C14A 120.6(10) . . ?
C16A C15A H15A 119.7 . . ?
C15A C16A C17A 118.3(12) . . ?
C15A C16A C19A 118.6(18) . . ?
C17A C16A C19A 123.1(18) . . ?
C16A C17A H17A 119.9 . . ?
C16A C17A C18A 120.2(12) . . ?
C18A C17A H17A 119.9 . . ?
C13A C18A C17A 121.9(11) . . ?
C13A C18A H18A 119.1 . . ?
C17A C18A H18A 119.1 . . ?
N3A C19A C16A 170(3) . . ?

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
O2 C20 C21 F1 -41.5(12) . . . . ?
O2 C20 C21 F2 79.4(11) . . . . ?
O2 C20 C21 F3 -172.2(9) . . . . ?
O3 C20 C21 F1 145.1(10) . . . . ?
O3 C20 C21 F2 -94.1(12) . . . . ?
O3 C20 C21 F3 14.4(15) . . . . ?
O1 C7 C8 C9 174.9(3) . . . . ?
O1 C7 C10 N2 -55.7(5) . . . . ?
O1 C11 C12 N2 55.2(7) . . . . ?
O1 C11 C12 C13 177.8(5) . . . . ?
N1 C4 C5 C6 -171.6(3) . . . . ?
N1 C4 C9 C8 174.5(4) . . . . ?
N2 C12 C13 C14 -149.6(6) . . . . ?
N2 C12 C13 C18 32.6(7) . . . . ?
C1 N1 C4 C5 -60.2(7) . . . . ?
C1 N1 C4 C9 178.3(6) . . . . ?
C4 N1 C1 C2 178.9(6) . . . . ?
C4 N1 C1 C3 -61.1(9) . . . . ?
C4 C5 C6 C7 54.1(4) . . . . ?
C5 C4 C9 C8 53.5(4) . . . . ?
C5 C6 C7 O1 -169.4(3) . . . . ?
C5 C6 C7 C8 -53.5(4) . . . . ?
C5 C6 C7 C10 69.8(4) . . . . ?
C6 C7 C8 C9 54.9(5) . . . . ?
C6 C7 C10 N2 67.4(5) . . . . ?
C7 O1 C11 C12 -58.6(6) . . . . ?
C7 C8 C9 C4 -55.6(4) . . . . ?
C8 C7 C10 N2 -170.3(4) . . . . ?
C9 C4 C5 C6 -53.1(4) . . . . ?
C10 N2 C12 C11 -56.7(7) . . . . ?
C10 N2 C12 C13 -177.6(5) . . . . ?
C10 C7 C8 C9 -69.0(4) . . . . ?
C11 O1 C7 C6 -66.6(5) . . . . ?
C11 O1 C7 C8 175.1(4) . . . . ?
C11 O1 C7 C10 56.7(5) . . . . ?
C11 C12 C13 C14 91.5(7) . . . . ?
C11 C12 C13 C18 -86.4(7) . . . . ?
C12 N2 C10 C7 59.5(6) . . . . ?
C12 C13 C14 C15 -177.4(4) . . . . ?
C12 C13 C18 C17 175.6(8) . . . . ?
C13 C14 C15 C16 -0.2(8) . . . . ?
C14 C13 C18 C17 -2.3(12) . . . . ?
C14 C15 C16 C17 1.6(11) . . . . ?
C14 C15 C16 C19 -177.6(7) . . . . ?
C15 C16 C17 C18 -3.3(14) . . . . ?
C16 C17 C18 C13 3.8(15) . . . . ?
C18 C13 C14 C15 0.5(8) . . . . ?
C19 C16 C17 C18 175.9(10) . . . . ?
F1A C21A C20A O2A 57.5(11) . . . . ?
F1A C21A C20A O3A -111.4(13) . . . . ?
F2A C21A C20A O2A 176.0(9) . . . . ?
F2A C21A C20A O3A 7.0(16) . . . . ?
F3A C21A C20A O2A -56.7(12) . . . . ?
F3A C21A C20A O3A 134.3(12) . . . . ?
C4A C9A C8A C7A -54.5(10) . . . . ?
C9A C4A C5A C6A -52.6(11) . . . . ?
C9A C4A N1A C1A -69(2) . . . . ?
C9A C8A C7A C6A 54.5(10) . . . . ?
C9A C8A C7A C10A 171.8(7) . . . . ?
C9A C8A C7A O1A -67.0(9) . . . . ?
C8A C7A C6A C5A -53.5(10) . . . . ?
C8A C7A C10A N2A 64.9(11) . . . . ?
C8A C7A O1A C11A -66.9(11) . . . . ?
C7A C6A C5A C4A 54.7(12) . . . . ?
C7A C10A N2A C12A 65.2(16) . . . . ?
C6A C7A C10A N2A -176.7(9) . . . . ?
C6A C7A O1A C11A 170.8(9) . . . . ?
C5A C4A C9A C8A 52.1(10) . . . . ?
C5A C4A N1A C1A 167.9(18) . . . . ?
C3A C1A N1A C4A -47(3) . . . . ?
C2A C1A N1A C4A -179.3(18) . . . . ?
N1A C4A C9A C8A -70.1(12) . . . . ?
N1A C4A C5A C6A 69.9(14) . . . . ?
C10A C7A C6A C5A -171.5(8) . . . . ?
C10A C7A O1A C11A 54.6(11) . . . . ?
C10A N2A C12A C11A -60.4(18) . . . . ?
C10A N2A C12A C13A -178.6(12) . . . . ?
N2A C12A C11A O1A 55.0(18) . . . . ?
N2A C12A C13A C14A -141.5(16) . . . . ?
N2A C12A C13A C18A 42.1(15) . . . . ?
C12A C11A O1A C7A -53.1(15) . . . . ?
C12A C13A C14A C15A 178.2(13) . . . . ?
C12A C13A C18A C17A -175.1(19) . . . . ?
C11A C12A C13A C14A 101.5(16) . . . . ?
C11A C12A C13A C18A -74.9(17) . . . . ?
O1A C7A C6A C5A 71.9(10) . . . . ?
O1A C7A C10A N2A -60.2(11) . . . . ?
C13A C12A C11A O1A 170.5(12) . . . . ?
C13A C14A C15A C16A 3(3) . . . . ?
C14A C13A C18A C17A 8(3) . . . . ?
C14A C15A C16A C17A -4(3) . . . . ?
C14A C15A C16A C19A 177(2) . . . . ?
C15A C16A C17A C18A 7(4) . . . . ?
C15A C16A C19A N3A 15(21) . . . . ?
C16A C17A C18A C13A -10(4) . . . . ?
C17A C16A C19A N3A -165(19) . . . . ?
C18A C13A C14A C15A -5(2) . . . . ?
C19A C16A C17A C18A -174(3) . . . . ?

_olex2_date_sample_data_collection 2020-10-27
_olex2_date_sample_submission    2020-10-27
_olex2_submission_original_sample_id jb241020_2_1
_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 1.401
_oxdiff_exptl_absorpt_empirical_full_min 0.728
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
