# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_af15
_database_code_depnum_ccdc_archive 'CCDC 2074037'
loop_
_audit_author_name
_audit_author_address
'guy clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2019-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H9 F9 N2 O'
_chemical_formula_sum            'C17 H9 F9 N2 O'
_chemical_formula_weight         428.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 F3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_H-M_alt        'P -3'
_space_group_name_Hall           '-P 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   19.50530(10)
_cell_length_b                   19.50530(10)
_cell_length_c                   7.90760(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2605.44(4)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    15568
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.7840
_cell_measurement_theta_min      4.5120
_shelx_estimated_absorpt_T_max   0.749
_shelx_estimated_absorpt_T_min   0.552
_exptl_absorpt_coefficient_mu    1.535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            22438
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.968
_diffrn_reflns_theta_min         4.534
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00   3.00   1.00    4.00    --  -41.46 125.00-150.00   95
  2  ω    -50.00  33.00   1.00    4.00    --  -41.46  38.00   0.00   83
  3  ω    -33.00  66.00   1.00    4.00    --   41.46 -38.00-150.00   99
  4  ω     41.00  98.00   1.00   16.00    --  114.00 -45.00 -60.00   57
  5  ω     38.00  91.00   1.00   16.00    --  114.00 -30.00 -60.00   53
  6  ω     41.00  98.00   1.00   16.00    --  114.00 -45.00  90.00   57
  7  ω     38.00  91.00   1.00   16.00    --  114.00 -30.00   0.00   53
  8  ω     41.00  98.00   1.00   16.00    --  114.00 -45.00 150.00   57
  9  ω     32.00 167.00   1.00   16.00    --  114.00 -15.00 -90.00  135
 10  ω    100.00 178.00   1.00   16.00    --  114.00 111.00-120.00   78
 11  ω     41.00  98.00   1.00   16.00    --  114.00 -45.00-120.00   57
 12  ω     32.00 167.00   1.00   16.00    --  114.00 -15.00  90.00  135
 13  ω   -114.00 -13.00   1.00    4.00    --  -41.46 -57.00-180.00  101
 14  ω   -114.00 -14.00   1.00    4.00    --  -41.46 -52.00 -68.00  100
 15  ω     38.00 113.00   1.00   16.00    --  114.00-111.00 -60.00   75
 16  ω     61.00 178.00   1.00   16.00    --  114.00  15.00   0.00  117
 17  ω     38.00 113.00   1.00   16.00    --  114.00-111.00  90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0613723000
_diffrn_orient_matrix_UB_12      -0.0001766000
_diffrn_orient_matrix_UB_13      -0.1229405000
_diffrn_orient_matrix_UB_21      -0.0423757000
_diffrn_orient_matrix_UB_22      -0.0910065000
_diffrn_orient_matrix_UB_23      -0.0088498000
_diffrn_orient_matrix_UB_31      -0.0524651000
_diffrn_orient_matrix_UB_32      -0.0054726000
_diffrn_orient_matrix_UB_33      0.1509438000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3548
_reflns_number_total             3692
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.08
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.8474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0910
_refine_special_details          ?
_olex2_refinement_description    
;
The NH was located in a difference map but refined with restraints
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N8(H8), C3(H3), C18(H18), C6(H6), C14(H14), C5(H5), C17(H17), C15(H15),
 C16(H16)
;
_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
F4A F 0.74744(4) 0.59879(5) 0.93385(10) 0.03725(19) Uani 1 1 d . . . . .
F12A F 0.31106(5) 0.52825(5) 0.51860(11) 0.0424(2) Uani 1 1 d . . . . .
F12B F 0.30218(5) 0.53581(5) 0.78939(11) 0.0437(2) Uani 1 1 d . . . . .
F1B F 0.44406(6) 0.31217(5) 0.98151(11) 0.0483(2) Uani 1 1 d . . . . .
F4B F 0.75212(5) 0.64181(6) 0.68357(11) 0.0482(2) Uani 1 1 d . . . . .
F1C F 0.45286(6) 0.29120(5) 0.72042(11) 0.0456(2) Uani 1 1 d . . . . .
F12C F 0.20974(5) 0.52727(5) 0.62800(14) 0.0503(2) Uani 1 1 d . . . . .
F4C F 0.71653(5) 0.68834(5) 0.89014(14) 0.0520(2) Uani 1 1 d . . . . .
F1A F 0.55268(6) 0.32618(5) 0.88213(15) 0.0569(3) Uani 1 1 d . . . . .
O11 O 0.14471(5) 0.37582(6) 0.64120(13) 0.0381(2) Uani 1 1 d . . . . .
N9 N 0.33674(6) 0.41812(6) 0.70228(12) 0.0268(2) Uani 1 1 d . . . . .
N8 N 0.38606(6) 0.39124(6) 0.73538(13) 0.0289(2) Uani 1 1 d . . . . .
H8 H 0.368620 0.340185 0.744921 0.035 Uiso 1 1 calc R . . . .
C10 C 0.26134(7) 0.36976(7) 0.69061(14) 0.0265(2) Uani 1 1 d . . . . .
C3 C 0.59944(7) 0.48078(7) 0.83449(15) 0.0277(2) Uani 1 1 d . . . . .
H3 H 0.635783 0.465474 0.874322 0.033 Uiso 1 1 calc R . . . .
C4 C 0.62522(7) 0.55961(7) 0.80006(14) 0.0262(2) Uani 1 1 d . . . . .
C18 C 0.24272(7) 0.23795(7) 0.60723(16) 0.0311(3) Uani 1 1 d . . . . .
H18 H 0.287233 0.264325 0.534508 0.037 Uiso 1 1 calc R . . . .
C7 C 0.46638(7) 0.44667(7) 0.75450(15) 0.0259(2) Uani 1 1 d . . . . .
C13 C 0.21866(7) 0.28193(7) 0.70421(15) 0.0270(2) Uani 1 1 d . . . . .
C2 C 0.52037(7) 0.42409(7) 0.81073(15) 0.0269(2) Uani 1 1 d . . . . .
C6 C 0.49372(7) 0.52622(7) 0.71611(16) 0.0294(2) Uani 1 1 d . . . . .
H6 H 0.457940 0.541862 0.674319 0.035 Uiso 1 1 calc R . . . .
C4A C 0.70976(7) 0.62174(7) 0.82661(16) 0.0300(3) Uani 1 1 d . . . . .
C14 C 0.15335(7) 0.24266(8) 0.81094(16) 0.0332(3) Uani 1 1 d . . . . .
H14 H 0.136506 0.272029 0.877646 0.040 Uiso 1 1 calc R . . . .
C11 C 0.21563(7) 0.41000(7) 0.65967(15) 0.0293(2) Uani 1 1 d . . . . .
C5 C 0.57240(7) 0.58202(7) 0.73869(16) 0.0285(2) Uani 1 1 d . . . . .
H5 H 0.590622 0.635946 0.712268 0.034 Uiso 1 1 calc R . . . .
C1 C 0.49362(8) 0.33898(7) 0.84944(17) 0.0318(3) Uani 1 1 d . . . . .
C12 C 0.26121(8) 0.50204(8) 0.64924(18) 0.0346(3) Uani 1 1 d . . . . .
C17 C 0.20197(9) 0.15583(8) 0.61640(19) 0.0396(3) Uani 1 1 d . . . . .
H17 H 0.218679 0.126149 0.550375 0.047 Uiso 1 1 calc R . . . .
C15 C 0.11310(8) 0.16073(9) 0.81947(18) 0.0410(3) Uani 1 1 d . . . . .
H15 H 0.068817 0.134093 0.892694 0.049 Uiso 1 1 calc R . . . .
C16 C 0.13697(9) 0.11735(8) 0.7220(2) 0.0442(3) Uani 1 1 d . . . . .
H16 H 0.108703 0.061171 0.727598 0.053 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F4A C4A 1.3376(14) . ?
F12A C12 1.3329(16) . ?
F12B C12 1.3320(16) . ?
F1B C1 1.3391(16) . ?
F4B C4A 1.3386(15) . ?
F1C C1 1.3419(15) . ?
F12C C12 1.3314(15) . ?
F4C C4A 1.3363(15) . ?
F1A C1 1.3205(15) . ?
O11 C11 1.2071(15) . ?
N9 N8 1.3316(14) . ?
N9 C10 1.2939(15) . ?
N8 H8 0.8800 . ?
N8 C7 1.3972(15) . ?
C10 C13 1.4877(16) . ?
C10 C11 1.4732(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3850(17) . ?
C3 C2 1.3897(17) . ?
C4 C4A 1.4945(16) . ?
C4 C5 1.3923(16) . ?
C18 H18 0.9500 . ?
C18 C13 1.3953(17) . ?
C18 C17 1.3891(18) . ?
C7 C2 1.4017(16) . ?
C7 C6 1.3988(16) . ?
C13 C14 1.3950(17) . ?
C2 C1 1.5018(16) . ?
C6 H6 0.9500 . ?
C6 C5 1.3788(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3858(19) . ?
C11 C12 1.5570(17) . ?
C5 H5 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(2) . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N9 N8 120.57(10) . . ?
N9 N8 H8 121.1 . . ?
N9 N8 C7 117.89(10) . . ?
C7 N8 H8 121.1 . . ?
N9 C10 C13 127.73(11) . . ?
N9 C10 C11 113.18(10) . . ?
C11 C10 C13 119.09(10) . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 119.95(10) . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C4A 120.90(10) . . ?
C3 C4 C5 120.14(11) . . ?
C5 C4 C4A 118.95(11) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C13 120.39(12) . . ?
N8 C7 C2 121.27(10) . . ?
N8 C7 C6 119.54(10) . . ?
C6 C7 C2 119.19(11) . . ?
C18 C13 C10 120.11(11) . . ?
C14 C13 C10 120.51(11) . . ?
C14 C13 C18 119.37(11) . . ?
C3 C2 C7 120.14(11) . . ?
C3 C2 C1 119.08(10) . . ?
C7 C2 C1 120.77(11) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.28(11) . . ?
C5 C6 H6 119.9 . . ?
F4A C4A F4B 105.75(10) . . ?
F4A C4A C4 112.70(10) . . ?
F4B C4A C4 112.82(10) . . ?
F4C C4A F4A 106.46(10) . . ?
F4C C4A F4B 106.67(11) . . ?
F4C C4A C4 111.95(10) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.86(12) . . ?
C15 C14 H14 120.1 . . ?
O11 C11 C10 123.88(11) . . ?
O11 C11 C12 117.80(11) . . ?
C10 C11 C12 118.31(10) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.24(11) . . ?
C6 C5 H5 119.9 . . ?
F1B C1 F1C 105.09(11) . . ?
F1B C1 C2 112.00(10) . . ?
F1C C1 C2 111.74(10) . . ?
F1A C1 F1B 107.53(11) . . ?
F1A C1 F1C 106.71(11) . . ?
F1A C1 C2 113.27(11) . . ?
F12A C12 C11 111.70(10) . . ?
F12B C12 F12A 108.24(11) . . ?
F12B C12 C11 112.43(11) . . ?
F12C C12 F12A 107.51(11) . . ?
F12C C12 F12B 107.40(11) . . ?
F12C C12 C11 109.36(10) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.84(13) . . ?
C16 C17 H17 120.1 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.49(13) . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.04(13) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N8 H8 F1B 0.88 2.60 3.0317(14) 111.1 . yes
N8 H8 F1C 0.88 2.28 2.8393(13) 120.9 . yes

_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 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.843
####################################################################### 
# 
# 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_af10
_database_code_depnum_ccdc_archive 'CCDC 2074038'
loop_
_audit_author_name
_audit_author_address
'guy clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2018-07-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 F3 N2 O'
_chemical_formula_sum            'C17 H15 F3 N2 O'
_chemical_formula_weight         320.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 F'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5454(2)
_cell_length_b                   8.12670(15)
_cell_length_c                   15.8452(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.6141(17)
_cell_angle_gamma                90
_cell_volume                     1530.96(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11061
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.6790
_cell_measurement_theta_min      5.4450
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.831
_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14916
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.806
_diffrn_reflns_theta_min         3.718
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.82 -37.00-180.00   99
  2  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00 -90.00  100
  3  ω     31.00 135.00   1.00    4.00    --  107.00 -30.00   0.00  104
  4  ω     24.00 110.00   1.00    4.00    --  107.00 -94.00 -90.00   86
  5  ω     35.00 136.00   1.00    4.00    --  107.00 -61.00-180.00  101
  6  ω     79.00 178.00   1.00    4.00    --  107.00  30.00   0.00   99
  7  ω     24.00 110.00   1.00    4.00    --  107.00 -94.00   0.00   86
  8  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00  90.00  100
  9  ω      1.00  83.00   1.00    1.00    --   41.82 -99.00-180.00   82
 10  ω     79.00 178.00   1.00    4.00    --  107.00  30.00-180.00   99
 11  ω     34.00 118.00   1.00    4.00    --  107.00-125.00-150.00   84
 12  ω     79.00 178.00   1.00    4.00    --  107.00  30.00 -90.00   99
 13  ω     79.00 178.00   1.00    4.00    --  107.00  30.00  90.00   99
 14  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00   0.00  100
 15  ω      1.00  83.00   1.00    1.00    --   41.82 -99.00 -30.00   82
 16  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 120.00  100
 17  ω     74.00 154.00   1.00    4.00    --  107.00  77.00 -90.00   80
 18  ω     78.00 178.00   1.00    4.00    --  107.00  61.00  30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0927952000
_diffrn_orient_matrix_UB_12      -0.0233976000
_diffrn_orient_matrix_UB_13      -0.0902441000
_diffrn_orient_matrix_UB_21      -0.0885266000
_diffrn_orient_matrix_UB_22      -0.0146622000
_diffrn_orient_matrix_UB_23      0.0482418000
_diffrn_orient_matrix_UB_31      -0.0183821000
_diffrn_orient_matrix_UB_32      0.1875375000
_diffrn_orient_matrix_UB_33      -0.0075705000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2889
_reflns_number_total             3052
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.6566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1042
_refine_special_details          ?
_olex2_refinement_description    
;
The NH was located in a difference map but placed at a calculated position for the refinement.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), C17(H17), C13(H13), C11(H11), C7(H7), C14(H14), C16(H16), C15(H15),
 C8(H8)
2.b Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C10A(H10A,H10B,H10C)
;
_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
F1A F 0.24901(6) 0.67257(11) 0.85278(6) 0.0350(2) Uani 1 1 d . . . . .
F1C F 0.33179(7) 0.45671(11) 0.92089(6) 0.0390(2) Uani 1 1 d . . . . .
O2 O 0.52513(7) 0.71032(11) 0.90024(5) 0.0264(2) Uani 1 1 d . . . . .
F1B F 0.37716(8) 0.69459(15) 0.97921(6) 0.0531(3) Uani 1 1 d . . . . .
N5 N 0.30731(8) 0.39902(13) 0.66428(6) 0.0228(2) Uani 1 1 d . . . . .
H5 H 0.362333 0.374439 0.643236 0.027 Uiso 1 1 calc R . . . .
N4 N 0.32880(8) 0.48135(13) 0.73913(6) 0.0214(2) Uani 1 1 d . . . . .
C3 C 0.42910(10) 0.54509(15) 0.77612(7) 0.0208(3) Uani 1 1 d . . . . .
C12 C 0.52300(9) 0.54565(15) 0.73777(7) 0.0204(3) Uani 1 1 d . . . . .
C6 C 0.19647(10) 0.34990(15) 0.61751(8) 0.0222(3) Uani 1 1 d . . . . .
C17 C 0.50370(10) 0.60433(15) 0.65119(8) 0.0239(3) Uani 1 1 d . . . . .
H17 H 0.430829 0.641790 0.617429 0.029 Uiso 1 1 calc R . . . .
C2 C 0.44295(10) 0.62957(16) 0.85942(7) 0.0218(3) Uani 1 1 d . . . . .
C13 C 0.63030(10) 0.49175(16) 0.78668(8) 0.0249(3) Uani 1 1 d . . . . .
H13 H 0.644421 0.451268 0.845485 0.030 Uiso 1 1 calc R . . . .
C11 C 0.17651(10) 0.27905(16) 0.53406(8) 0.0243(3) Uani 1 1 d . . . . .
H11 H 0.237755 0.258972 0.512432 0.029 Uiso 1 1 calc R . . . .
C10 C 0.06778(10) 0.23707(16) 0.48170(8) 0.0254(3) Uani 1 1 d . . . . .
C7 C 0.10845(11) 0.37781(17) 0.65101(8) 0.0276(3) Uani 1 1 d . . . . .
H7 H 0.121811 0.424882 0.708339 0.033 Uiso 1 1 calc R . . . .
C14 C 0.71658(11) 0.49709(17) 0.74965(9) 0.0295(3) Uani 1 1 d . . . . .
H14 H 0.789796 0.460902 0.783390 0.035 Uiso 1 1 calc R . . . .
C16 C 0.59016(11) 0.60830(17) 0.61417(8) 0.0279(3) Uani 1 1 d . . . . .
H16 H 0.576336 0.647437 0.555139 0.033 Uiso 1 1 calc R . . . .
C9 C -0.02215(10) 0.26683(17) 0.51428(8) 0.0270(3) Uani 1 1 d . . . . .
C15 C 0.69658(11) 0.55498(17) 0.66363(9) 0.0295(3) Uani 1 1 d . . . . .
H15 H 0.756018 0.558053 0.638603 0.035 Uiso 1 1 calc R . . . .
C1 C 0.34788(11) 0.61292(17) 0.90257(8) 0.0276(3) Uani 1 1 d . . . . .
C8 C 0.00045(11) 0.33526(18) 0.59867(9) 0.0301(3) Uani 1 1 d . . . . .
H8 H -0.060183 0.353498 0.621258 0.036 Uiso 1 1 calc R . . . .
C9A C -0.14137(11) 0.2256(2) 0.45930(10) 0.0356(3) Uani 1 1 d . . . . .
H9AA H -0.158369 0.275567 0.400164 0.053 Uiso 1 1 calc GR . . . .
H9AB H -0.193349 0.268681 0.488788 0.053 Uiso 1 1 calc GR . . . .
H9AC H -0.149842 0.105940 0.453219 0.053 Uiso 1 1 calc GR . . . .
C10A C 0.04762(12) 0.1643(2) 0.39038(9) 0.0354(3) Uani 1 1 d . . . . .
H10A H -0.001920 0.237154 0.345474 0.053 Uiso 1 1 calc GR . . . .
H10B H 0.012120 0.056121 0.387346 0.053 Uiso 1 1 calc GR . . . .
H10C H 0.119543 0.152465 0.378968 0.053 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C1 1.3308(15) . ?
F1C C1 1.3319(17) . ?
O2 C2 1.2191(15) . ?
F1B C1 1.3286(15) . ?
N5 H5 0.8800 . ?
N5 N4 1.3127(14) . ?
N5 C6 1.4086(15) . ?
N4 C3 1.3131(15) . ?
C3 C12 1.4879(16) . ?
C3 C2 1.4482(16) . ?
C12 C17 1.3986(16) . ?
C12 C13 1.3923(17) . ?
C6 C11 1.3897(17) . ?
C6 C7 1.3880(17) . ?
C17 H17 0.9500 . ?
C17 C16 1.3884(17) . ?
C2 C1 1.5585(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3869(18) . ?
C11 H11 0.9500 . ?
C11 C10 1.3939(17) . ?
C10 C9 1.4035(18) . ?
C10 C10A 1.5077(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3877(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3870(19) . ?
C16 H16 0.9500 . ?
C16 C15 1.3844(19) . ?
C9 C8 1.3912(19) . ?
C9 C9A 1.5088(17) . ?
C15 H15 0.9500 . ?
C8 H8 0.9500 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 N5 H5 119.9 . . ?
N4 N5 C6 120.22(10) . . ?
C6 N5 H5 119.9 . . ?
N5 N4 C3 119.70(10) . . ?
N4 C3 C12 126.14(10) . . ?
N4 C3 C2 114.39(10) . . ?
C2 C3 C12 119.37(10) . . ?
C17 C12 C3 119.34(10) . . ?
C13 C12 C3 121.51(10) . . ?
C13 C12 C17 119.15(11) . . ?
C11 C6 N5 117.76(11) . . ?
C7 C6 N5 121.65(11) . . ?
C7 C6 C11 120.52(11) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.56(11) . . ?
C16 C17 H17 119.7 . . ?
O2 C2 C3 125.02(11) . . ?
O2 C2 C1 116.74(10) . . ?
C3 C2 C1 118.21(10) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.08(11) . . ?
C14 C13 H13 120.0 . . ?
C6 C11 H11 119.6 . . ?
C6 C11 C10 120.84(11) . . ?
C10 C11 H11 119.6 . . ?
C11 C10 C9 119.19(11) . . ?
C11 C10 C10A 119.99(11) . . ?
C9 C10 C10A 120.81(11) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.36(11) . . ?
C8 C7 H7 120.8 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.37(12) . . ?
C15 C14 H14 119.8 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.73(11) . . ?
C15 C16 H16 120.1 . . ?
C10 C9 C9A 120.96(12) . . ?
C8 C9 C10 118.77(11) . . ?
C8 C9 C9A 120.27(12) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.11(12) . . ?
C16 C15 H15 119.9 . . ?
F1A C1 F1C 107.40(10) . . ?
F1A C1 C2 114.03(10) . . ?
F1C C1 C2 111.64(11) . . ?
F1B C1 F1A 107.06(11) . . ?
F1B C1 F1C 107.09(11) . . ?
F1B C1 C2 109.30(10) . . ?
C7 C8 C9 122.31(12) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C9 C9A H9AA 109.5 . . ?
C9 C9A H9AB 109.5 . . ?
C9 C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C10 C10A H10A 109.5 . . ?
C10 C10A H10B 109.5 . . ?
C10 C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O2 0.88 2.21 3.0311(13) 155.9 2_646 yes

_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 2.377
_oxdiff_exptl_absorpt_empirical_full_min 0.752
####################################################################### 
# 
# 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_af9
_database_code_depnum_ccdc_archive 'CCDC 2074039'
loop_
_audit_author_name
_audit_author_address
'guy clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2021-06-07 downloaded from the CCDC.
;
_audit_creation_date             2018-07-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 F3 N2 O'
_chemical_formula_sum            'C17 H15 F3 N2 O'
_chemical_formula_weight         320.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 F3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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_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'

_cell_length_a                   8.14933(8)
_cell_length_b                   10.51816(9)
_cell_length_c                   36.3202(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3113.22(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    17061
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.4110
_cell_measurement_theta_min      4.3340
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.833
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            30520
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.649
_diffrn_reflns_theta_min         4.376
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.82 -37.00  90.00   99
  2  ω      1.00  83.00   1.00    1.00    --   41.82 -99.00-180.00   82
  3  ω     23.00  98.00   1.00    1.00    --   41.82-125.00 -30.00   75
  4  ω     81.00 178.00   1.00    3.13    --  107.00  45.00 -60.00   97
  5  ω     31.00 135.00   1.00    3.13    --  107.00 -30.00 120.00  104
  6  ω     35.00 136.00   1.00    3.13    --  107.00 -61.00 -30.00  101
  7  ω     81.00 178.00   1.00    3.13    --  107.00  45.00   0.00   97
  8  ω   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00-120.00  109
  9  ω   -118.00  -9.00   1.00    1.00    --  -41.82 -77.00   0.00  109
 10  ω     81.00 178.00   1.00    3.13    --  107.00  45.00 120.00   97
 11  ω     79.00 178.00   1.00    3.13    --  107.00  30.00-150.00   99
 12  ω     24.00 110.00   1.00    3.13    --  107.00 -94.00 150.00   86
 13  ω     34.00 118.00   1.00    3.13    --  107.00-125.00 -30.00   84
 14  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00  60.00  100
 15  ω      1.00  83.00   1.00    1.00    --   41.82 -99.00  90.00   82
 16  ω     81.00 178.00   1.00    3.13    --  107.00  45.00  60.00   97
 17  ω     80.00 172.00   1.00    3.13    --  107.00  52.00-115.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1185151000
_diffrn_orient_matrix_UB_12      -0.0190898000
_diffrn_orient_matrix_UB_13      -0.0325715000
_diffrn_orient_matrix_UB_21      0.0178080000
_diffrn_orient_matrix_UB_22      -0.1452176000
_diffrn_orient_matrix_UB_23      0.0038614000
_diffrn_orient_matrix_UB_31      -0.1461803000
_diffrn_orient_matrix_UB_32      -0.0022333000
_diffrn_orient_matrix_UB_33      0.0268915000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                5983
_reflns_number_total             6180
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
The crystal chosen had racemic twinning. The ratio of the two possible chiral domains in the crystal 
refined to 0.84:0.16 using the TWIN and BASF commands in Shelxl.

;
_refine_ls_abs_structure_Flack   0.16(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.3880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0697
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;

The NHs were located in a difference map but placed at a calculated position for the refinement.
1. Twinned data refinement
 Scales: 0.84(10)
 0.16(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N105(H105), N205(H205), C211(H211), C113(H113), C210(H210), C213(H213),
 C117(H117), C217(H217), C208(H208), C111(H111), C108(H108), C110(H110),
 C114(H114), C116(H116), C214(H214), C216(H216), C215(H215), C115(H115)
3.b Idealised Me refined as rotating group:
 C27A(H27A,H27B,H27C), C17A(H17A,H17B,H17C), C29A(H29A,H29B,H29C), C19A(H19A,
 H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1B F 0.35125(13) 0.87219(10) 0.59968(3) 0.0344(2) Uani 1 1 d . . . . .
F1E F 0.83929(14) 0.85998(10) 0.66260(3) 0.0375(2) Uani 1 1 d . . . . .
F1C F 0.08968(13) 0.90124(11) 0.60014(3) 0.0397(3) Uani 1 1 d . . . . .
F1F F 0.58255(14) 0.90517(12) 0.65940(3) 0.0451(3) Uani 1 1 d . . . . .
F1A F 0.25153(19) 1.04782(10) 0.61891(3) 0.0485(3) Uani 1 1 d . . . . .
F1D F 0.76191(19) 1.04313(10) 0.64359(4) 0.0518(3) Uani 1 1 d . . . . .
O102 O 0.22443(18) 0.95173(12) 0.68340(3) 0.0365(3) Uani 1 1 d . . . . .
O008 O 0.74095(19) 0.95244(12) 0.57797(4) 0.0412(3) Uani 1 1 d . . . . .
N104 N 0.19115(17) 0.67318(13) 0.63371(4) 0.0255(3) Uani 1 1 d . . . . .
N204 N 0.66610(18) 0.66989(13) 0.62406(4) 0.0275(3) Uani 1 1 d . . . . .
N105 N 0.16984(19) 0.54900(13) 0.63325(4) 0.0279(3) Uani 1 1 d . . . . .
H105 H 0.150692 0.507373 0.653820 0.033 Uiso 1 1 calc R . . . .
N205 N 0.6329(2) 0.54717(13) 0.61960(4) 0.0291(3) Uani 1 1 d . . . . .
H205 H 0.651839 0.510737 0.598204 0.035 Uiso 1 1 calc R . . . .
C206 C 0.5677(2) 0.47487(15) 0.64876(4) 0.0259(3) Uani 1 1 d . . . . .
C207 C 0.5236(2) 0.34862(15) 0.64149(5) 0.0270(3) Uani 1 1 d . . . . .
C203 C 0.6995(2) 0.73781(16) 0.59505(4) 0.0264(3) Uani 1 1 d . . . . .
C102 C 0.2147(2) 0.87352(16) 0.65923(5) 0.0265(3) Uani 1 1 d . . . . .
C212 C 0.7023(2) 0.68774(16) 0.55671(4) 0.0266(3) Uani 1 1 d . . . . .
C101 C 0.2278(2) 0.92279(16) 0.61892(5) 0.0297(4) Uani 1 1 d . . . . .
C103 C 0.1851(2) 0.73743(15) 0.66449(4) 0.0249(3) Uani 1 1 d . . . . .
C112 C 0.1465(2) 0.68691(15) 0.70160(5) 0.0269(3) Uani 1 1 d . . . . .
C106 C 0.1781(2) 0.48346(16) 0.59936(5) 0.0271(3) Uani 1 1 d . . . . .
C211 C 0.5447(2) 0.52778(16) 0.68347(5) 0.0298(4) Uani 1 1 d . . . . .
H211 H 0.579205 0.612396 0.688335 0.036 Uiso 1 1 calc R . . . .
C107 C 0.1069(2) 0.36244(16) 0.59703(5) 0.0305(4) Uani 1 1 d . . . . .
C202 C 0.7233(2) 0.87338(16) 0.60187(5) 0.0300(4) Uani 1 1 d . . . . .
C113 C 0.2366(2) 0.72471(18) 0.73244(5) 0.0330(4) Uani 1 1 d . . . . .
H113 H 0.323792 0.783932 0.729790 0.040 Uiso 1 1 calc R . . . .
C210 C 0.4709(2) 0.45619(17) 0.71093(5) 0.0326(4) Uani 1 1 d . . . . .
H210 H 0.455092 0.492357 0.734631 0.039 Uiso 1 1 calc R . . . .
C201 C 0.7264(2) 0.91980(17) 0.64240(5) 0.0324(4) Uani 1 1 d . . . . .
C213 C 0.8095(2) 0.58953(17) 0.54766(5) 0.0325(4) Uani 1 1 d . . . . .
H213 H 0.885185 0.559007 0.565475 0.039 Uiso 1 1 calc R . . . .
C117 C 0.0161(2) 0.60195(17) 0.70625(5) 0.0312(4) Uani 1 1 d . . . . .
H117 H -0.048890 0.578247 0.685648 0.037 Uiso 1 1 calc R . . . .
C217 C 0.5949(3) 0.73355(18) 0.53011(5) 0.0353(4) Uani 1 1 d . . . . .
H217 H 0.523251 0.802068 0.535757 0.042 Uiso 1 1 calc R . . . .
C209 C 0.4199(2) 0.33212(17) 0.70424(5) 0.0326(4) Uani 1 1 d . . . . .
C208 C 0.4491(2) 0.28040(16) 0.66972(5) 0.0316(4) Uani 1 1 d . . . . .
H208 H 0.416839 0.195026 0.665174 0.038 Uiso 1 1 calc R . . . .
C111 C 0.2491(2) 0.54024(17) 0.56880(5) 0.0314(4) Uani 1 1 d . . . . .
H111 H 0.298448 0.621766 0.570882 0.038 Uiso 1 1 calc R . . . .
C108 C 0.1093(2) 0.30230(17) 0.56288(5) 0.0352(4) Uani 1 1 d . . . . .
H108 H 0.062692 0.219832 0.560794 0.042 Uiso 1 1 calc R . . . .
C110 C 0.2480(3) 0.47773(18) 0.53526(5) 0.0356(4) Uani 1 1 d . . . . .
H110 H 0.296240 0.517249 0.514384 0.043 Uiso 1 1 calc R . . . .
C114 C 0.1991(3) 0.6761(2) 0.76689(5) 0.0412(4) Uani 1 1 d . . . . .
H114 H 0.260202 0.702587 0.787800 0.049 Uiso 1 1 calc R . . . .
C116 C -0.0191(3) 0.55207(19) 0.74070(5) 0.0380(4) Uani 1 1 d . . . . .
H116 H -0.106052 0.492714 0.743570 0.046 Uiso 1 1 calc R . . . .
C109 C 0.1774(3) 0.35831(18) 0.53162(5) 0.0375(4) Uani 1 1 d . . . . .
C214 C 0.8063(3) 0.53607(19) 0.51281(5) 0.0384(4) Uani 1 1 d . . . . .
H214 H 0.880158 0.469350 0.506763 0.046 Uiso 1 1 calc R . . . .
C27A C 0.5524(2) 0.28969(16) 0.60408(5) 0.0343(4) Uani 1 1 d . . . . .
H27A H 0.482888 0.331978 0.585789 0.052 Uiso 1 1 calc GR . . . .
H27B H 0.525133 0.199009 0.604993 0.052 Uiso 1 1 calc GR . . . .
H27C H 0.667983 0.299887 0.597204 0.052 Uiso 1 1 calc GR . . . .
C216 C 0.5924(3) 0.6793(2) 0.49539(5) 0.0429(5) Uani 1 1 d . . . . .
H216 H 0.518788 0.710829 0.477267 0.051 Uiso 1 1 calc R . . . .
C17A C 0.0255(3) 0.30201(18) 0.62996(5) 0.0375(4) Uani 1 1 d . . . . .
H17A H 0.106334 0.291137 0.649689 0.056 Uiso 1 1 calc GR . . . .
H17B H -0.018910 0.218855 0.622977 0.056 Uiso 1 1 calc GR . . . .
H17C H -0.063814 0.356777 0.638616 0.056 Uiso 1 1 calc GR . . . .
C215 C 0.6963(3) 0.5795(2) 0.48692(5) 0.0423(5) Uani 1 1 d . . . . .
H215 H 0.691815 0.541060 0.463276 0.051 Uiso 1 1 calc R . . . .
C115 C 0.0731(3) 0.5892(2) 0.77095(5) 0.0426(5) Uani 1 1 d . . . . .
H115 H 0.049538 0.554744 0.794549 0.051 Uiso 1 1 calc R . . . .
C29A C 0.3312(3) 0.2575(2) 0.73364(6) 0.0464(5) Uani 1 1 d . . . . .
H29A H 0.368536 0.285491 0.757979 0.070 Uiso 1 1 calc GR . . . .
H29B H 0.354615 0.166751 0.730606 0.070 Uiso 1 1 calc GR . . . .
H29C H 0.212760 0.271925 0.731439 0.070 Uiso 1 1 calc GR . . . .
C19A C 0.1715(3) 0.2933(2) 0.49448(6) 0.0516(6) Uani 1 1 d . . . . .
H19A H 0.282286 0.266673 0.487410 0.077 Uiso 1 1 calc GR . . . .
H19B H 0.128368 0.352628 0.476046 0.077 Uiso 1 1 calc GR . . . .
H19C H 0.099853 0.218664 0.495931 0.077 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1B C101 1.336(2) . ?
F1E C201 1.335(2) . ?
F1C C101 1.335(2) . ?
F1F C201 1.334(2) . ?
F1A C101 1.329(2) . ?
F1D C201 1.330(2) . ?
O102 C102 1.206(2) . ?
O008 C202 1.211(2) . ?
N104 N105 1.3178(19) . ?
N104 C103 1.307(2) . ?
N204 N205 1.329(2) . ?
N204 C203 1.302(2) . ?
N105 H105 0.8800 . ?
N105 C106 1.412(2) . ?
N205 H205 0.8800 . ?
N205 C206 1.408(2) . ?
C206 C207 1.401(2) . ?
C206 C211 1.391(2) . ?
C207 C208 1.391(2) . ?
C207 C27A 1.512(2) . ?
C203 C212 1.489(2) . ?
C203 C202 1.460(2) . ?
C102 C101 1.557(2) . ?
C102 C103 1.464(2) . ?
C212 C213 1.392(3) . ?
C212 C217 1.390(2) . ?
C103 C112 1.483(2) . ?
C112 C113 1.397(2) . ?
C112 C117 1.399(2) . ?
C106 C107 1.401(2) . ?
C106 C111 1.387(2) . ?
C211 H211 0.9500 . ?
C211 C210 1.387(2) . ?
C107 C108 1.393(3) . ?
C107 C17A 1.508(3) . ?
C202 C201 1.551(3) . ?
C113 H113 0.9500 . ?
C113 C114 1.386(3) . ?
C210 H210 0.9500 . ?
C210 C209 1.391(3) . ?
C213 H213 0.9500 . ?
C213 C214 1.385(3) . ?
C117 H117 0.9500 . ?
C117 C116 1.387(2) . ?
C217 H217 0.9500 . ?
C217 C216 1.384(3) . ?
C209 C208 1.387(3) . ?
C209 C29A 1.510(3) . ?
C208 H208 0.9500 . ?
C111 H111 0.9500 . ?
C111 C110 1.384(2) . ?
C108 H108 0.9500 . ?
C108 C109 1.394(3) . ?
C110 H110 0.9500 . ?
C110 C109 1.388(3) . ?
C114 H114 0.9500 . ?
C114 C115 1.383(3) . ?
C116 H116 0.9500 . ?
C116 C115 1.387(3) . ?
C109 C19A 1.513(3) . ?
C214 H214 0.9500 . ?
C214 C215 1.378(3) . ?
C27A H27A 0.9800 . ?
C27A H27B 0.9800 . ?
C27A H27C 0.9800 . ?
C216 H216 0.9500 . ?
C216 C215 1.383(3) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C215 H215 0.9500 . ?
C115 H115 0.9500 . ?
C29A H29A 0.9800 . ?
C29A H29B 0.9800 . ?
C29A H29C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C103 N104 N105 121.23(14) . . ?
C203 N204 N205 118.47(14) . . ?
N104 N105 H105 120.4 . . ?
N104 N105 C106 119.26(14) . . ?
C106 N105 H105 120.4 . . ?
N204 N205 H205 119.7 . . ?
N204 N205 C206 120.64(14) . . ?
C206 N205 H205 119.7 . . ?
C207 C206 N205 117.84(15) . . ?
C211 C206 N205 121.11(15) . . ?
C211 C206 C207 121.04(15) . . ?
C206 C207 C27A 121.22(15) . . ?
C208 C207 C206 117.51(16) . . ?
C208 C207 C27A 121.25(15) . . ?
N204 C203 C212 124.48(15) . . ?
N204 C203 C202 115.23(15) . . ?
C202 C203 C212 120.14(14) . . ?
O102 C102 C101 116.94(15) . . ?
O102 C102 C103 125.65(16) . . ?
C103 C102 C101 117.35(14) . . ?
C213 C212 C203 119.55(15) . . ?
C217 C212 C203 121.19(16) . . ?
C217 C212 C213 119.21(16) . . ?
F1B C101 C102 114.25(14) . . ?
F1C C101 F1B 107.47(14) . . ?
F1C C101 C102 111.49(14) . . ?
F1A C101 F1B 106.52(15) . . ?
F1A C101 F1C 106.90(15) . . ?
F1A C101 C102 109.85(14) . . ?
N104 C103 C102 112.80(14) . . ?
N104 C103 C112 126.89(15) . . ?
C102 C103 C112 120.26(14) . . ?
C113 C112 C103 121.05(16) . . ?
C113 C112 C117 118.96(16) . . ?
C117 C112 C103 119.97(16) . . ?
C107 C106 N105 118.44(16) . . ?
C111 C106 N105 120.46(15) . . ?
C111 C106 C107 121.04(16) . . ?
C206 C211 H211 120.2 . . ?
C210 C211 C206 119.55(16) . . ?
C210 C211 H211 120.2 . . ?
C106 C107 C17A 121.14(17) . . ?
C108 C107 C106 117.42(17) . . ?
C108 C107 C17A 121.41(16) . . ?
O008 C202 C203 124.40(17) . . ?
O008 C202 C201 117.53(16) . . ?
C203 C202 C201 118.07(14) . . ?
C112 C113 H113 119.9 . . ?
C114 C113 C112 120.21(18) . . ?
C114 C113 H113 119.9 . . ?
C211 C210 H210 119.6 . . ?
C211 C210 C209 120.90(17) . . ?
C209 C210 H210 119.6 . . ?
F1E C201 C202 112.62(15) . . ?
F1F C201 F1E 107.27(15) . . ?
F1F C201 C202 112.88(15) . . ?
F1D C201 F1E 106.96(15) . . ?
F1D C201 F1F 106.79(16) . . ?
F1D C201 C202 109.97(15) . . ?
C212 C213 H213 119.8 . . ?
C214 C213 C212 120.37(17) . . ?
C214 C213 H213 119.8 . . ?
C112 C117 H117 119.7 . . ?
C116 C117 C112 120.51(18) . . ?
C116 C117 H117 119.7 . . ?
C212 C217 H217 120.0 . . ?
C216 C217 C212 120.00(18) . . ?
C216 C217 H217 120.0 . . ?
C210 C209 C29A 120.48(18) . . ?
C208 C209 C210 118.32(16) . . ?
C208 C209 C29A 121.18(18) . . ?
C207 C208 H208 118.7 . . ?
C209 C208 C207 122.60(16) . . ?
C209 C208 H208 118.7 . . ?
C106 C111 H111 120.1 . . ?
C110 C111 C106 119.78(16) . . ?
C110 C111 H111 120.1 . . ?
C107 C108 H108 118.7 . . ?
C107 C108 C109 122.62(17) . . ?
C109 C108 H108 118.7 . . ?
C111 C110 H110 119.4 . . ?
C111 C110 C109 121.11(18) . . ?
C109 C110 H110 119.4 . . ?
C113 C114 H114 119.9 . . ?
C115 C114 C113 120.26(19) . . ?
C115 C114 H114 119.9 . . ?
C117 C116 H116 120.1 . . ?
C117 C116 C115 119.75(19) . . ?
C115 C116 H116 120.1 . . ?
C108 C109 C19A 121.49(18) . . ?
C110 C109 C108 118.01(17) . . ?
C110 C109 C19A 120.48(19) . . ?
C213 C214 H214 120.0 . . ?
C215 C214 C213 120.07(18) . . ?
C215 C214 H214 120.0 . . ?
C207 C27A H27A 109.5 . . ?
C207 C27A H27B 109.5 . . ?
C207 C27A H27C 109.5 . . ?
H27A C27A H27B 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
C217 C216 H216 119.8 . . ?
C215 C216 C217 120.40(18) . . ?
C215 C216 H216 119.8 . . ?
C107 C17A H17A 109.5 . . ?
C107 C17A H17B 109.5 . . ?
C107 C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C214 C215 C216 119.91(18) . . ?
C214 C215 H215 120.0 . . ?
C216 C215 H215 120.0 . . ?
C114 C115 C116 120.25(17) . . ?
C114 C115 H115 119.9 . . ?
C116 C115 H115 119.9 . . ?
C209 C29A H29A 109.5 . . ?
C209 C29A H29B 109.5 . . ?
C209 C29A H29C 109.5 . . ?
H29A C29A H29B 109.5 . . ?
H29A C29A H29C 109.5 . . ?
H29B C29A H29C 109.5 . . ?
C109 C19A H19A 109.5 . . ?
C109 C19A H19B 109.5 . . ?
C109 C19A H19C 109.5 . . ?
H19A C19A H19B 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.213
_oxdiff_exptl_absorpt_empirical_full_min 0.803
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.84(10)
2 0.16(10)
