# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_jb080616_1_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1833580'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_audit_creation_date             2016-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 B Br F3 N'
_chemical_formula_sum            'C11 H12 B Br F3 N'
_chemical_formula_weight         305.94
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.1247(8)
_cell_length_b                   11.1474(11)
_cell_length_c                   11.9275(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.442(3)
_cell_angle_gamma                90
_cell_volume                     1213.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.535
_exptl_absorpt_coefficient_mu    3.401
_exptl_absorpt_correction_T_max  0.7302
_exptl_absorpt_correction_T_min  0.5817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1262 before and 0.0655 after correction.
The Ratio of minimum to maximum transmission is 0.7966.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22040
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_min         2.501
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Bruker/Nonius Kappa Apex2'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms high brilliance'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                5500
_reflns_number_total             5908
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 2415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5908
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0191
_refine_ls_restrained_S_all      0.918
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0384
_refine_ls_wR_factor_ref         0.0389
_refine_special_details          'Disorder in one CF3 group.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F2-B1 \\sim F2A-B1 \\sim F3-B1 \\sim F3A-B1 \\sim F1-B1 \\sim F1A-B1
 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
3. Rigid bond restraints
 F3, F2, F1, B1, F2A, F3A, F1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
5. Rigid body (RIGU) restrains
 F3, F2, F1, B1, F2A, F3A, F1A, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F2A)=Sof(F3A)=Sof(F1A)=1-FVAR(1)
 Sof(F3)=Sof(F2)=Sof(F1)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C19(H19A,H19B), C9(H9A,H9B), C22(H22A,H22B), C20(H20A,H20B),
 C11(H11A,H11B), C10(H10A,H10B), C21(H21A,H21B)
7.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C6(H6), C17(H17), C14(H14), C3(H3), C16(H16), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.075
;
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
Br1 Br 0.34975(3) -0.04069(2) 0.91328(2) 0.02278(7) Uani 1 1 d . . . . .
Br2 Br 0.11187(3) 0.49971(2) 0.09125(2) 0.02557(7) Uani 1 1 d . . . . .
F6 F 0.21144(15) 1.04147(12) 0.52052(12) 0.0215(3) Uani 1 1 d . . . . .
F4 F 0.04478(14) 0.91050(13) 0.44681(12) 0.0230(3) Uani 1 1 d . . . . .
F5 F 0.12771(15) 0.88569(13) 0.62669(12) 0.0201(3) Uani 1 1 d . . . . .
F3 F 0.322(4) 0.653(2) 0.6668(18) 0.024(3) Uani 0.38(4) 1 d D U P A 1
F2 F 0.421(3) 0.625(2) 0.8405(10) 0.036(3) Uani 0.38(4) 1 d D U P A 1
F1 F 0.467(2) 0.4924(14) 0.6997(16) 0.032(3) Uani 0.38(4) 1 d D U P A 1
N2 N 0.4316(2) 0.84047(17) 0.51579(17) 0.0147(4) Uani 1 1 d . . . . .
N1 N 0.08661(19) 0.52349(17) 0.78238(16) 0.0135(4) Uani 1 1 d . . . . .
C5 C 0.1916(2) 0.2607(2) 0.7493(2) 0.0138(5) Uani 1 1 d . . . . .
H5 H 0.1321 0.2766 0.6853 0.017 Uiso 1 1 calc R . . . .
C18 C 0.3020(2) 0.8361(2) 0.47253(19) 0.0125(5) Uani 1 1 d . . . . .
C15 C 0.2711(2) 0.7498(2) 0.3808(2) 0.0123(5) Uani 1 1 d . . . . .
C4 C 0.2463(2) 0.3554(2) 0.8135(2) 0.0129(5) Uani 1 1 d . . . . .
C13 C 0.1264(2) 0.5817(2) 0.3159(2) 0.0152(5) Uani 1 1 d . . . . .
H13 H 0.0604 0.5177 0.3304 0.018 Uiso 1 1 calc R . . . .
C8 C -0.0486(2) 0.4541(2) 0.81159(19) 0.0159(5) Uani 1 1 d . . . . .
H8A H -0.0425 0.4231 0.8893 0.019 Uiso 1 1 calc R . . . .
H8B H -0.0629 0.3857 0.7596 0.019 Uiso 1 1 calc R . . . .
C6 C 0.2242(2) 0.1425(2) 0.7791(2) 0.0156(5) Uani 1 1 d . . . . .
H6 H 0.1889 0.0775 0.7350 0.019 Uiso 1 1 calc R . . . .
C12 C 0.1804(2) 0.5999(2) 0.2091(2) 0.0143(5) Uani 1 1 d . . . . .
C19 C 0.5584(2) 0.7623(2) 0.4848(2) 0.0201(6) Uani 1 1 d . . . . .
H19A H 0.5827 0.7716 0.4045 0.024 Uiso 1 1 calc R . . . .
H19B H 0.5364 0.6769 0.4999 0.024 Uiso 1 1 calc R . . . .
C17 C 0.2817(2) 0.6889(2) 0.1861(2) 0.0167(5) Uani 1 1 d . . . . .
H17 H 0.3184 0.6989 0.1124 0.020 Uiso 1 1 calc R . . . .
C14 C 0.1701(2) 0.6582(2) 0.4013(2) 0.0143(5) Uani 1 1 d . . . . .
H14 H 0.1312 0.6484 0.4744 0.017 Uiso 1 1 calc R . . . .
C3 C 0.3351(2) 0.3314(2) 0.9067(2) 0.0148(5) Uani 1 1 d . . . . .
H3 H 0.3760 0.3961 0.9484 0.018 Uiso 1 1 calc R . . . .
C9 C -0.1725(3) 0.5447(2) 0.7994(2) 0.0234(6) Uani 1 1 d . . . . .
H9A H -0.2157 0.5421 0.7231 0.028 Uiso 1 1 calc R . . . .
H9B H -0.2505 0.5292 0.8548 0.028 Uiso 1 1 calc R . . . .
C22 C 0.4722(3) 0.9148(2) 0.6147(2) 0.0203(6) Uani 1 1 d . . . . .
H22A H 0.3909 0.9184 0.6691 0.024 Uiso 1 1 calc R . . . .
H22B H 0.4981 0.9975 0.5918 0.024 Uiso 1 1 calc R . . . .
C7 C 0.2195(2) 0.4839(2) 0.78269(18) 0.0149(5) Uani 1 1 d . U . . .
C16 C 0.3287(3) 0.7632(2) 0.2728(2) 0.0159(5) Uani 1 1 d . . . . .
H16 H 0.4001 0.8234 0.2588 0.019 Uiso 1 1 calc R . . . .
C2 C 0.3643(2) 0.2144(2) 0.9391(2) 0.0150(5) Uani 1 1 d . . . . .
H2 H 0.4208 0.1980 1.0045 0.018 Uiso 1 1 calc R . . . .
C20 C 0.6838(3) 0.8068(2) 0.5596(2) 0.0242(6) Uani 1 1 d . . . . .
H20A H 0.7381 0.8730 0.5233 0.029 Uiso 1 1 calc R . . . .
H20B H 0.7529 0.7411 0.5779 0.029 Uiso 1 1 calc R . . . .
C11 C 0.0461(3) 0.6517(2) 0.7609(2) 0.0207(5) Uani 1 1 d . . . . .
H11A H 0.0346 0.6675 0.6796 0.025 Uiso 1 1 calc R . . . .
H11B H 0.1206 0.7070 0.7924 0.025 Uiso 1 1 calc R . . . .
C10 C -0.0992(3) 0.6643(2) 0.8214(2) 0.0235(6) Uani 1 1 d . . . . .
H10A H -0.0839 0.6777 0.9026 0.028 Uiso 1 1 calc R . . . .
H10B H -0.1579 0.7312 0.7900 0.028 Uiso 1 1 calc R . . . .
C21 C 0.6038(3) 0.8506(2) 0.6644(2) 0.0200(6) Uani 1 1 d . . . . .
H21A H 0.5734 0.7826 0.7123 0.024 Uiso 1 1 calc R . . . .
H21B H 0.6658 0.9060 0.7090 0.024 Uiso 1 1 calc R . . . .
C1 C 0.3089(2) 0.1216(2) 0.8737(2) 0.0138(5) Uani 1 1 d . . . . .
B1 B 0.3607(3) 0.5701(3) 0.7508(3) 0.0236(7) Uani 1 1 d D U . . .
B2 B 0.1657(3) 0.9221(3) 0.5187(2) 0.0159(6) Uani 1 1 d . . . . .
F2A F 0.3820(15) 0.6489(9) 0.8445(7) 0.0335(16) Uani 0.62(4) 1 d D U P A 2
F3A F 0.330(2) 0.6357(14) 0.6557(9) 0.029(2) Uani 0.62(4) 1 d D U P A 2
F1A F 0.4835(9) 0.5014(9) 0.7381(19) 0.046(2) Uani 0.62(4) 1 d D U P A 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
Br1 C1 1.906(2) . ?
Br2 C12 1.898(2) . ?
F6 B2 1.395(3) . ?
F4 B2 1.398(3) . ?
F5 B2 1.396(3) . ?
F3 B1 1.409(14) . ?
F2 B1 1.348(11) . ?
F1 B1 1.439(10) . ?
N2 C18 1.287(3) . ?
N2 C19 1.497(3) . ?
N2 C22 1.486(3) . ?
N1 C8 1.500(3) . ?
N1 C7 1.291(3) . ?
N1 C11 1.498(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.394(3) . ?
C5 C6 1.397(3) . ?
C18 C15 1.483(3) . ?
C18 B2 1.667(3) . ?
C15 C14 1.398(3) . ?
C15 C16 1.403(3) . ?
C4 C3 1.397(3) . ?
C4 C7 1.498(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.384(3) . ?
C13 C14 1.384(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.523(3) . ?
C6 H6 0.9500 . ?
C6 C1 1.382(3) . ?
C12 C17 1.384(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.528(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.390(3) . ?
C14 H14 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.386(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.513(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C21 1.514(3) . ?
C7 B1 1.654(3) . ?
C16 H16 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.388(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.533(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.520(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
B1 F2A 1.434(8) . ?
B1 F3A 1.377(9) . ?
B1 F1A 1.367(8) . ?

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
C18 N2 C19 126.0(2) . . ?
C18 N2 C22 124.21(19) . . ?
C22 N2 C19 109.38(17) . . ?
C7 N1 C8 126.7(2) . . ?
C7 N1 C11 123.9(2) . . ?
C11 N1 C8 109.25(18) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
N2 C18 C15 119.3(2) . . ?
N2 C18 B2 122.1(2) . . ?
C15 C18 B2 118.60(19) . . ?
C14 C15 C18 117.8(2) . . ?
C14 C15 C16 119.4(2) . . ?
C16 C15 C18 122.5(2) . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 C7 122.2(2) . . ?
C3 C4 C7 118.1(2) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 118.9(2) . . ?
C14 C13 H13 120.5 . . ?
N1 C8 H8A 110.9 . . ?
N1 C8 H8B 110.9 . . ?
N1 C8 C9 104.3(2) . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C5 C6 H6 120.6 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 H6 120.6 . . ?
C13 C12 Br2 118.54(18) . . ?
C17 C12 Br2 119.43(18) . . ?
C17 C12 C13 122.0(2) . . ?
N2 C19 H19A 110.9 . . ?
N2 C19 H19B 110.9 . . ?
N2 C19 C20 104.10(19) . . ?
H19A C19 H19B 109.0 . . ?
C20 C19 H19A 110.9 . . ?
C20 C19 H19B 110.9 . . ?
C12 C17 H17 120.6 . . ?
C12 C17 C16 118.8(2) . . ?
C16 C17 H17 120.6 . . ?
C15 C14 H14 119.8 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.6 . . ?
C8 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 C8 103.96(19) . . ?
C10 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
N2 C22 H22A 111.0 . . ?
N2 C22 H22B 111.0 . . ?
N2 C22 C21 103.85(19) . . ?
H22A C22 H22B 109.0 . . ?
C21 C22 H22A 111.0 . . ?
C21 C22 H22B 111.0 . . ?
N1 C7 C4 118.6(2) . . ?
N1 C7 B1 122.3(2) . . ?
C4 C7 B1 119.10(18) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C3 C2 H2 120.8 . . ?
C3 C2 C1 118.5(2) . . ?
C1 C2 H2 120.8 . . ?
C19 C20 H20A 111.2 . . ?
C19 C20 H20B 111.2 . . ?
C19 C20 C21 102.71(19) . . ?
H20A C20 H20B 109.1 . . ?
C21 C20 H20A 111.2 . . ?
C21 C20 H20B 111.2 . . ?
N1 C11 H11A 111.2 . . ?
N1 C11 H11B 111.2 . . ?
N1 C11 C10 102.84(19) . . ?
H11A C11 H11B 109.1 . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
C9 C10 C11 102.8(2) . . ?
C9 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
C22 C21 C20 102.3(2) . . ?
C22 C21 H21A 111.3 . . ?
C22 C21 H21B 111.3 . . ?
C20 C21 H21A 111.3 . . ?
C20 C21 H21B 111.3 . . ?
H21A C21 H21B 109.2 . . ?
C6 C1 Br1 117.97(18) . . ?
C6 C1 C2 122.2(2) . . ?
C2 C1 Br1 119.88(18) . . ?
F3 B1 F1 105.3(11) . . ?
F3 B1 C7 110.7(15) . . ?
F2 B1 F3 111.4(12) . . ?
F2 B1 F1 109.6(7) . . ?
F2 B1 C7 113.3(7) . . ?
F1 B1 C7 106.0(8) . . ?
F2A B1 C7 106.1(5) . . ?
F3A B1 C7 110.0(9) . . ?
F3A B1 F2A 110.0(7) . . ?
F1A B1 C7 109.9(5) . . ?
F1A B1 F2A 108.9(5) . . ?
F1A B1 F3A 111.7(9) . . ?
F6 B2 F4 109.4(2) . . ?
F6 B2 F5 109.8(2) . . ?
F6 B2 C18 109.24(19) . . ?
F4 B2 C18 109.4(2) . . ?
F5 B2 F4 109.8(2) . . ?
F5 B2 C18 109.2(2) . . ?

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
Br2 C12 C17 C16 178.69(17) . . . . ?
N2 C18 C15 C14 115.6(2) . . . . ?
N2 C18 C15 C16 -70.2(3) . . . . ?
N2 C18 B2 F6 52.1(3) . . . . ?
N2 C18 B2 F4 171.8(2) . . . . ?
N2 C18 B2 F5 -68.0(3) . . . . ?
N2 C19 C20 C21 30.6(3) . . . . ?
N2 C22 C21 C20 37.0(2) . . . . ?
N1 C8 C9 C10 -27.1(2) . . . . ?
N1 C7 B1 F3 -34.9(12) . . . . ?
N1 C7 B1 F2 91.1(14) . . . . ?
N1 C7 B1 F1 -148.6(9) . . . . ?
N1 C7 B1 F2A 73.3(6) . . . . ?
N1 C7 B1 F3A -45.7(8) . . . . ?
N1 C7 B1 F1A -169.2(10) . . . . ?
N1 C11 C10 C9 -37.7(3) . . . . ?
C5 C4 C3 C2 -2.9(3) . . . . ?
C5 C4 C7 N1 63.7(3) . . . . ?
C5 C4 C7 B1 -116.6(3) . . . . ?
C5 C6 C1 Br1 179.25(16) . . . . ?
C5 C6 C1 C2 -0.9(3) . . . . ?
C18 N2 C19 C20 179.1(2) . . . . ?
C18 N2 C22 C21 154.9(2) . . . . ?
C18 C15 C14 C13 174.0(2) . . . . ?
C18 C15 C16 C17 -171.7(2) . . . . ?
C15 C18 B2 F6 -129.5(2) . . . . ?
C15 C18 B2 F4 -9.9(3) . . . . ?
C15 C18 B2 F5 110.3(2) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C3 C2 C1 3.0(3) . . . . ?
C4 C7 B1 F3 145.3(12) . . . . ?
C4 C7 B1 F2 -88.7(14) . . . . ?
C4 C7 B1 F1 31.6(10) . . . . ?
C4 C7 B1 F2A -106.5(6) . . . . ?
C4 C7 B1 F3A 134.5(8) . . . . ?
C4 C7 B1 F1A 11.1(10) . . . . ?
C13 C12 C17 C16 -1.0(3) . . . . ?
C8 N1 C7 C4 0.8(3) . . . . ?
C8 N1 C7 B1 -178.9(2) . . . . ?
C8 N1 C11 C10 21.3(3) . . . . ?
C8 C9 C10 C11 40.5(3) . . . . ?
C6 C5 C4 C3 0.8(3) . . . . ?
C6 C5 C4 C7 177.5(2) . . . . ?
C12 C13 C14 C15 -2.2(3) . . . . ?
C12 C17 C16 C15 -1.6(3) . . . . ?
C19 N2 C18 C15 -2.1(3) . . . . ?
C19 N2 C18 B2 176.2(2) . . . . ?
C19 N2 C22 C21 -18.3(3) . . . . ?
C19 C20 C21 C22 -41.9(3) . . . . ?
C14 C15 C16 C17 2.3(3) . . . . ?
C14 C13 C12 Br2 -176.77(17) . . . . ?
C14 C13 C12 C17 3.0(3) . . . . ?
C3 C4 C7 N1 -119.5(2) . . . . ?
C3 C4 C7 B1 60.2(3) . . . . ?
C3 C2 C1 Br1 178.70(16) . . . . ?
C3 C2 C1 C6 -1.1(3) . . . . ?
C22 N2 C18 C15 -174.1(2) . . . . ?
C22 N2 C18 B2 4.2(3) . . . . ?
C22 N2 C19 C20 -7.9(3) . . . . ?
C7 N1 C8 C9 178.9(2) . . . . ?
C7 N1 C11 C10 -154.3(2) . . . . ?
C7 C4 C3 C2 -179.8(2) . . . . ?
C16 C15 C14 C13 -0.4(3) . . . . ?
C11 N1 C8 C9 3.4(2) . . . . ?
C11 N1 C7 C4 175.7(2) . . . . ?
C11 N1 C7 B1 -4.1(4) . . . . ?
B2 C18 C15 C14 -62.7(3) . . . . ?
B2 C18 C15 C16 111.4(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-06-08
_olex2_date_sample_submission    2016-06-07
_olex2_submission_original_sample_id jb080616_1_1
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jb211116_1_1
_database_code_depnum_ccdc_archive 'CCDC 1833584'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_audit_creation_date             2016-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 B F4 N'
_chemical_formula_sum            'C8 H8 B F4 N'
_chemical_formula_weight         204.96
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H8 B1 F4 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.1042(2)
_cell_length_b                   37.0556(10)
_cell_length_c                   7.9394(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.529(3)
_cell_angle_gamma                90
_cell_volume                     1792.45(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13847
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.6570
_cell_measurement_theta_min      4.7500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.308
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.753
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.9f (Rigaku Oxford Diffraction, 2015)
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    1.519
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 5 0.0609
-3 3 -3 0.0729
0 23 1 0.0225
2 21 -1 0.0396
3 -9 2 0.0572
0 -11 5 0.0562
2 -19 1 0.0443
3 -16 -1 0.0661
-3 13 1 0.0535
0 24 0 0.0200
0 -24 0 0.0145
-1 -24 0 0.0235
-4 2 -1 0.0694
-4 3 1 0.0622
0 -2 -5 0.0596
4 -8 1 0.0612
4 -5 -1 0.0750

_exptl_crystal_size_max          0.141
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.036
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
-0.3903 2.0111 5.0038 0.7535 -0.5657 0.2517
-2.8098 2.9957 -3.0037 -0.5245 0.5060 0.6172
0.3978 22.9856 0.9967 0.7801 0.5936 0.0490
1.7955 20.9798 -1.0043 0.5219 0.7681 -0.3623
3.4096 -8.9949 2.0041 0.2565 -0.5752 -0.8241
-0.1875 -10.9802 5.0062 0.4203 -0.9776 0.1355
2.2083 -18.9882 1.0048 -0.2266 -0.7501 -0.6096
3.0043 -15.9964 -0.9972 -0.3883 -0.4113 -0.8479
-3.2039 12.9988 0.9978 0.2965 0.3190 0.8815
-0.2051 23.9835 -0.0045 0.6254 0.7585 0.1729
0.0049 -23.9832 0.0044 -0.6375 -0.7563 -0.1238
-0.7959 -23.9818 0.0042 -0.6859 -0.7473 0.0727
-3.8065 2.0028 -1.0021 -0.3218 0.2324 0.9149
-4.0027 3.0072 0.9994 -0.0175 0.0129 1.0264
0.3903 -2.0111 -5.0038 -0.7535 0.5657 -0.2517
3.6075 -7.9983 1.0031 0.1503 -0.4193 -0.8967
3.8029 -5.0054 -0.9991 -0.0477 -0.0737 -0.9876

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0071
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6644
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.072
_diffrn_reflns_theta_min         4.774
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  24.36   0.38    1.50    --  -50.21  19.00 -30.00  222
  2  ω   -121.00 -35.88   0.38    1.50    --  -50.21 -57.00 -30.00  224
  3  ω   -120.00 -39.06   0.38    1.50    --  -50.21-178.00-120.00  213
  4  ω    -76.00   3.80   0.38    9.00    --  -70.00  19.00  90.00  210
  5  ω   -140.00 -70.84   0.38    9.00    --  -70.00-125.00  60.00  182
  6  ω     33.00  74.80   0.38    9.00    --  107.75 -19.00  60.00  110
  7  ω     33.00  68.72   0.38    9.00    --  107.75 -38.00 -30.00   94
  8  ω     33.00  74.80   0.38    9.00    --  107.75 -19.00 -90.00  110
  9  ω     39.00 110.06   0.38    9.00    --  107.75 -99.00-120.00  187
 10  ω     33.00  74.80   0.38    9.00    --  107.75 -19.00   0.00  110
 11  ω     33.00  68.72   0.38    9.00    --  107.75 -38.00  60.00   94
 12  ω     33.00  68.72   0.38    9.00    --  107.75 -38.00 -60.00   94
 13  ω     39.00 110.06   0.38    9.00    --  107.75 -99.00-180.00  187
 14  ω     37.00 105.02   0.38    9.00    --  107.75 -57.00 120.00  179
 15  ω     33.00  74.80   0.38    9.00    --  107.75 -19.00 150.00  110
 16  ω     33.00  68.72   0.38    9.00    --  107.75 -38.00 150.00   94
 17  ω     37.00 105.02   0.38    9.00    --  107.75 -57.00 -90.00  179
 18  ω     33.00  68.72   0.38    9.00    --  107.75 -38.00  90.00   94
 19  ω     37.00 105.02   0.38    9.00    --  107.75 -57.00-150.00  179
 20  ω     33.00  68.72   0.38    9.00    --  107.75 -38.00-180.00   94
 21  ω   -121.00 -35.88   0.38    1.50    --  -50.21 -57.00  30.00  224
 22  ω   -115.00 -29.12   0.38    1.50    --  -50.21 -77.00 120.00  226
 23  ω   -115.00 -29.12   0.38    1.50    --  -50.21 -77.00 -90.00  226
 24  ω   -135.00 -47.98   0.38    9.00    --  -70.00 -77.00-150.00  229
 25  ω   -135.00 -47.98   0.38    9.00    --  -70.00 -77.00 -60.00  229
 26  ω     97.00 177.18   0.38    9.00    --  107.75  19.00 120.00  211
 27  ω     98.00 168.68   0.38    9.00    --  107.75  38.00 -30.00  186
 28  ω     97.00 177.18   0.38    9.00    --  107.75  19.00  60.00  211
 29  ω     39.00 110.06   0.38    9.00    --  107.75 -99.00  60.00  187
;
_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      0.0604759000
_diffrn_orient_matrix_UB_12      0.0266207000
_diffrn_orient_matrix_UB_13      0.1445977000
_diffrn_orient_matrix_UB_21      -0.0111635000
_diffrn_orient_matrix_UB_22      0.0315078000
_diffrn_orient_matrix_UB_23      -0.1265839000
_diffrn_orient_matrix_UB_31      -0.2453189000
_diffrn_orient_matrix_UB_32      0.0051166000
_diffrn_orient_matrix_UB_33      0.0291041000
_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              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          
'Crystal twinned with twin law 1 0 0 0 -1 0 0 0 -1.'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6029
_reflns_number_total             6644
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _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 1.171.39.9f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         6644
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0653
_refine_ls_restrained_S_all      1.099
_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)+(0.1057P)²+0.9150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.1980
_refine_special_details          'HKLF5 used for final refinements.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6815(17) 0.3185(17)
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. Restrained distances
 N1A-H1A = N1B-H1B
 0.93 with sigma of 0.02
 F1C-B1B \\sim F1B-B1B \\sim F3C-B1B \\sim F3B-B1B \\sim F2C-B1B \\sim F2B-B1B
 with sigma of 0.02
 F1B-F2B \\sim F2B-F3B \\sim F3B-F1B \\sim F1C-F2C \\sim F2C-F3C \\sim F3C-F1C
 with sigma of 0.02
4. Rigid body (RIGU) restrains
 F1B, F2B, F3B, B1B, F2C, F1C, F3C, C2B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F2C)=Sof(F1C)=Sof(F3C)=1-FVAR(1)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C7A(H7A), C8A(H8A), C4B(H4B), C5B(H5B), C7B(H7B), C8B(H8B)
6.b Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
;
_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
F1A F 1.1956(3) 0.65429(4) 0.2204(2) 0.0410(4) Uani 1 1 d . . . . .
F2A F 1.2179(3) 0.67876(5) 0.4810(2) 0.0508(5) Uani 1 1 d . . . . .
F3A F 1.0790(3) 0.71159(4) 0.2543(2) 0.0497(5) Uani 1 1 d . . . . .
F4A F 0.7432(3) 0.51274(4) 0.4680(3) 0.0525(5) Uani 1 1 d . . . . .
N1A N 0.6738(4) 0.68029(6) 0.3800(3) 0.0351(5) Uani 1 1 d D . . . .
H1A H 0.543(4) 0.6695(8) 0.401(4) 0.042 Uiso 1 1 d DR . . . .
C1A C 0.6532(5) 0.71952(7) 0.3717(4) 0.0429(7) Uani 1 1 d . . . . .
H1AA H 0.6337 0.7271 0.2535 0.064 Uiso 1 1 calc GR . . . .
H1AB H 0.7862 0.7307 0.4240 0.064 Uiso 1 1 calc GR . . . .
H1AC H 0.5258 0.7271 0.4322 0.064 Uiso 1 1 calc GR . . . .
C2A C 0.8462(4) 0.66085(7) 0.3631(3) 0.0332(6) Uani 1 1 d . . . . .
C3A C 0.8195(4) 0.62153(7) 0.3834(3) 0.0336(6) Uani 1 1 d . . . . .
C4A C 0.9892(4) 0.60130(7) 0.4620(4) 0.0378(6) Uani 1 1 d . . . . .
H4A H 1.1240 0.6128 0.4960 0.045 Uiso 1 1 calc R . . . .
C5A C 0.9640(5) 0.56476(8) 0.4911(4) 0.0421(7) Uani 1 1 d . . . . .
H5A H 1.0786 0.5511 0.5469 0.051 Uiso 1 1 calc R . . . .
C6A C 0.7693(5) 0.54861(7) 0.4374(4) 0.0408(6) Uani 1 1 d . . . . .
C7A C 0.5997(5) 0.56721(8) 0.3559(4) 0.0426(7) Uani 1 1 d . . . . .
H7A H 0.4680 0.5552 0.3188 0.051 Uiso 1 1 calc R . . . .
C8A C 0.6247(4) 0.60384(7) 0.3290(4) 0.0378(6) Uani 1 1 d . . . . .
H8A H 0.5087 0.6171 0.2731 0.045 Uiso 1 1 calc R . . . .
B1A B 1.0914(5) 0.67785(8) 0.3268(4) 0.0368(7) Uani 1 1 d . . . . .
F1B F 0.7162(17) 0.6485(3) 1.0037(11) 0.0396(13) Uani 0.73(4) 1 d D U P A 1
F2B F 0.6779(11) 0.6656(3) 0.7302(6) 0.0515(17) Uani 0.73(4) 1 d D U P A 1
F3B F 0.5822(17) 0.70363(17) 0.9390(19) 0.0564(18) Uani 0.73(4) 1 d D U P A 1
F4B F 0.2715(3) 0.49995(4) 0.9102(3) 0.0512(5) Uani 1 1 d . . . . .
N1B N 0.1578(4) 0.66831(6) 0.8474(3) 0.0353(5) Uani 1 1 d D . . . .
H1B H 0.021(4) 0.6572(8) 0.844(4) 0.042 Uiso 1 1 d DR . . . .
C1B C 0.1341(5) 0.70764(7) 0.8352(4) 0.0393(6) Uani 1 1 d . . . . .
H1BA H 0.0012 0.7135 0.7651 0.059 Uiso 1 1 calc GR . . . .
H1BB H 0.2624 0.7179 0.7841 0.059 Uiso 1 1 calc GR . . . .
H1BC H 0.1230 0.7178 0.9483 0.059 Uiso 1 1 calc GR . . . .
C2B C 0.3367(4) 0.64989(7) 0.8686(3) 0.0333(6) Uani 1 1 d . U . . .
C3B C 0.3145(4) 0.61033(7) 0.8794(3) 0.0337(6) Uani 1 1 d . . . . .
C4B C 0.4733(4) 0.58824(7) 0.8112(4) 0.0365(6) Uani 1 1 d . . . . .
H4B H 0.5931 0.5989 0.7588 0.044 Uiso 1 1 calc R . . . .
C5B C 0.4576(5) 0.55096(7) 0.8192(4) 0.0408(6) Uani 1 1 d . . . . .
H5B H 0.5631 0.5359 0.7708 0.049 Uiso 1 1 calc R . . . .
C6B C 0.2849(5) 0.53636(7) 0.8993(4) 0.0410(6) Uani 1 1 d . . . . .
C7B C 0.1261(5) 0.55689(8) 0.9690(4) 0.0424(7) Uani 1 1 d . . . . .
H7B H 0.0090 0.5458 1.0233 0.051 Uiso 1 1 calc R . . . .
C8B C 0.1410(4) 0.59410(7) 0.9582(4) 0.0376(6) Uani 1 1 d . . . . .
H8B H 0.0322 0.6088 1.0048 0.045 Uiso 1 1 calc R . . . .
B1B B 0.5837(5) 0.66890(8) 0.8863(4) 0.0358(6) Uani 1 1 d D U . . .
F2C F 0.645(4) 0.6805(11) 0.7296(15) 0.059(5) Uani 0.27(4) 1 d D U P A 2
F1C F 0.730(5) 0.6455(6) 0.961(4) 0.046(5) Uani 0.27(4) 1 d D U P A 2
F3C F 0.566(5) 0.7001(5) 0.987(3) 0.045(4) Uani 0.27(4) 1 d D U P A 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
F1A B1A 1.395(3) . ?
F2A B1A 1.407(4) . ?
F3A B1A 1.377(4) . ?
F4A C6A 1.362(3) . ?
N1A H1A 0.92(2) . ?
N1A C1A 1.460(3) . ?
N1A C2A 1.289(3) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2A C3A 1.476(4) . ?
C2A B1A 1.665(4) . ?
C3A C4A 1.394(4) . ?
C3A C8A 1.402(4) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.384(4) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.375(4) . ?
C6A C7A 1.372(4) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.384(4) . ?
C8A H8A 0.9500 . ?
F1B B1B 1.415(6) . ?
F2B B1B 1.403(5) . ?
F3B B1B 1.354(7) . ?
F4B C6B 1.355(3) . ?
N1B H1B 0.93(2) . ?
N1B C1B 1.467(3) . ?
N1B C2B 1.290(3) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
C2B C3B 1.475(4) . ?
C2B B1B 1.662(4) . ?
C3B C4B 1.403(4) . ?
C3B C8B 1.399(4) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.386(4) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.376(4) . ?
C6B C7B 1.375(4) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.385(4) . ?
C8B H8B 0.9500 . ?
B1B F2C 1.389(12) . ?
B1B F1C 1.351(15) . ?
B1B F3C 1.413(13) . ?

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
C1A N1A H1A 112(2) . . ?
C2A N1A H1A 120(2) . . ?
C2A N1A C1A 128.3(2) . . ?
N1A C1A H1AA 109.5 . . ?
N1A C1A H1AB 109.5 . . ?
N1A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N1A C2A C3A 116.3(2) . . ?
N1A C2A B1A 123.7(2) . . ?
C3A C2A B1A 119.9(2) . . ?
C4A C3A C2A 119.7(2) . . ?
C4A C3A C8A 118.6(2) . . ?
C8A C3A C2A 121.7(2) . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A C3A 120.9(3) . . ?
C5A C4A H4A 119.6 . . ?
C4A C5A H5A 120.7 . . ?
C6A C5A C4A 118.5(3) . . ?
C6A C5A H5A 120.7 . . ?
F4A C6A C5A 118.6(3) . . ?
F4A C6A C7A 118.7(3) . . ?
C7A C6A C5A 122.7(3) . . ?
C6A C7A H7A 120.7 . . ?
C6A C7A C8A 118.6(3) . . ?
C8A C7A H7A 120.7 . . ?
C3A C8A H8A 119.7 . . ?
C7A C8A C3A 120.7(3) . . ?
C7A C8A H8A 119.7 . . ?
F1A B1A F2A 107.2(2) . . ?
F1A B1A C2A 108.4(2) . . ?
F2A B1A C2A 108.0(2) . . ?
F3A B1A F1A 109.3(2) . . ?
F3A B1A F2A 110.8(2) . . ?
F3A B1A C2A 112.9(2) . . ?
C1B N1B H1B 111(2) . . ?
C2B N1B H1B 121(2) . . ?
C2B N1B C1B 127.8(2) . . ?
N1B C1B H1BA 109.5 . . ?
N1B C1B H1BB 109.5 . . ?
N1B C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
N1B C2B C3B 116.9(2) . . ?
N1B C2B B1B 122.9(2) . . ?
C3B C2B B1B 120.2(2) . . ?
C4B C3B C2B 119.3(2) . . ?
C8B C3B C2B 121.9(2) . . ?
C8B C3B C4B 118.8(2) . . ?
C3B C4B H4B 119.6 . . ?
C5B C4B C3B 120.8(3) . . ?
C5B C4B H4B 119.6 . . ?
C4B C5B H5B 121.0 . . ?
C6B C5B C4B 118.1(3) . . ?
C6B C5B H5B 121.0 . . ?
F4B C6B C5B 118.2(3) . . ?
F4B C6B C7B 118.6(3) . . ?
C7B C6B C5B 123.2(3) . . ?
C6B C7B H7B 120.8 . . ?
C6B C7B C8B 118.4(3) . . ?
C8B C7B H7B 120.8 . . ?
C3B C8B H8B 119.7 . . ?
C7B C8B C3B 120.7(3) . . ?
C7B C8B H8B 119.7 . . ?
F1B B1B C2B 108.0(5) . . ?
F2B B1B F1B 106.7(4) . . ?
F2B B1B C2B 107.9(3) . . ?
F3B B1B F1B 108.6(5) . . ?
F3B B1B F2B 111.5(4) . . ?
F3B B1B C2B 113.9(5) . . ?
F2C B1B C2B 110.3(8) . . ?
F2C B1B F3C 106.6(11) . . ?
F1C B1B C2B 109.6(14) . . ?
F1C B1B F2C 112.6(11) . . ?
F1C B1B F3C 110.4(13) . . ?
F3C B1B C2B 107.1(12) . . ?

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
F4A C6A C7A C8A 178.3(3) . . . . ?
N1A C2A C3A C4A -143.2(3) . . . . ?
N1A C2A C3A C8A 35.3(4) . . . . ?
N1A C2A B1A F1A -144.5(3) . . . . ?
N1A C2A B1A F2A 99.6(3) . . . . ?
N1A C2A B1A F3A -23.2(4) . . . . ?
C1A N1A C2A C3A 178.0(3) . . . . ?
C1A N1A C2A B1A 0.0(4) . . . . ?
C2A C3A C4A C5A 176.4(3) . . . . ?
C2A C3A C8A C7A -177.2(3) . . . . ?
C3A C2A B1A F1A 37.6(3) . . . . ?
C3A C2A B1A F2A -78.3(3) . . . . ?
C3A C2A B1A F3A 158.8(2) . . . . ?
C3A C4A C5A C6A 1.4(4) . . . . ?
C4A C3A C8A C7A 1.3(4) . . . . ?
C4A C5A C6A F4A -179.1(3) . . . . ?
C4A C5A C6A C7A 0.2(5) . . . . ?
C5A C6A C7A C8A -1.0(5) . . . . ?
C6A C7A C8A C3A 0.2(4) . . . . ?
C8A C3A C4A C5A -2.2(4) . . . . ?
B1A C2A C3A C4A 34.9(4) . . . . ?
B1A C2A C3A C8A -146.6(3) . . . . ?
F4B C6B C7B C8B 179.7(3) . . . . ?
N1B C2B C3B C4B 145.0(3) . . . . ?
N1B C2B C3B C8B -36.1(4) . . . . ?
N1B C2B B1B F1B 144.0(5) . . . . ?
N1B C2B B1B F2B -101.1(6) . . . . ?
N1B C2B B1B F3B 23.3(8) . . . . ?
N1B C2B B1B F2C -75.5(19) . . . . ?
N1B C2B B1B F1C 160.0(16) . . . . ?
N1B C2B B1B F3C 40.2(12) . . . . ?
C1B N1B C2B C3B 179.1(2) . . . . ?
C1B N1B C2B B1B 0.0(4) . . . . ?
C2B C3B C4B C5B 179.9(2) . . . . ?
C2B C3B C8B C7B -178.9(3) . . . . ?
C3B C2B B1B F1B -35.1(5) . . . . ?
C3B C2B B1B F2B 79.9(6) . . . . ?
C3B C2B B1B F3B -155.8(7) . . . . ?
C3B C2B B1B F2C 105.5(19) . . . . ?
C3B C2B B1B F1C -19.1(16) . . . . ?
C3B C2B B1B F3C -138.9(12) . . . . ?
C3B C4B C5B C6B -1.5(4) . . . . ?
C4B C3B C8B C7B 0.1(4) . . . . ?
C4B C5B C6B F4B -178.8(2) . . . . ?
C4B C5B C6B C7B 1.0(5) . . . . ?
C5B C6B C7B C8B -0.1(5) . . . . ?
C6B C7B C8B C3B -0.5(4) . . . . ?
C8B C3B C4B C5B 0.9(4) . . . . ?
B1B C2B C3B C4B -35.9(4) . . . . ?
B1B C2B C3B C8B 143.0(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-22
_olex2_date_sample_submission    2016-11-21
_olex2_submission_original_sample_id jb211116_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.312
_oxdiff_exptl_absorpt_empirical_full_min 0.619
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6815(17) 23983 1777 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.3185(17) 24018 1777 nmt 0.9995 0.0000 0.0949 -0.0014 -0.9998 0.0114 -0.0006
-0.0000 -1.0002

_twin_special_details            
;
Component 2 rotated by -179.9876° 
 around [1.00 -0.00 -0.00] (reciprocal) or [1.00 0.00 0.05] (direct)
;
####################################################################### 
# 
# 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_jb190917_2_1
_database_code_depnum_ccdc_archive 'CCDC 1833583'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_audit_creation_date             2017-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H18 B F4 N'
_chemical_formula_sum            'C13 H18 B F4 N'
_chemical_formula_weight         275.09
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H18BF4N
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.48310(10)
_cell_length_b                   8.79060(10)
_cell_length_c                   17.8568(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1331.61(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18033
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.2460
_cell_measurement_theta_min      4.9160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
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    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 6 0.0162
0 -5 -6 0.0225
5 -1 3 0.0685
0 -3 10 0.0492
-4 -2 7 0.0681
-5 1 -2 0.0849
0 3 -10 0.0447
5 1 -5 0.0790
0 -5 5 0.0464
-5 -3 2 0.0664
0 5 -5 0.0373
0 -6 1 0.0380
1 6 0 0.0405
4 4 1 0.0624
-4 -2 -6 0.0723
0 -2 -11 0.0365
3 -2 -8 0.0572
-3 0 -9 0.0670
-1 2 11 0.0441
1 -1 11 0.0556
0 -1 12 0.0459
-4 1 7 0.0639
-3 -4 -5 0.0507
0 -5 -4 0.0225
2 -5 -3 0.0375
-4 4 1 0.0628

_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.039
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 5.0000 6.0000 -0.2468 0.9860 -0.0522
-0.0000 -5.0000 -6.0000 0.2468 -0.9860 0.0522
5.0000 -1.0000 2.9999 -0.0232 0.0259 0.9594
-0.0000 -3.0000 10.0000 -0.9329 -0.2311 0.3123
-4.0000 -2.0000 7.0001 -0.8574 -0.2346 -0.4747
-5.0000 1.0000 -1.9999 -0.0563 0.0007 -0.9387
0.0000 3.0000 -10.0000 0.9329 0.2311 -0.3123
5.0000 1.0000 -5.0001 0.7047 0.1446 0.7237
-0.0000 -5.0000 5.0000 -0.6275 -0.6944 0.2794
-5.0000 -3.0000 2.0001 -0.5583 -0.5549 -0.7152
0.0000 5.0000 -5.0000 0.6275 0.6944 -0.2794
-0.0000 -6.0000 1.0000 -0.3556 -0.9659 0.2320
1.0000 6.0000 -0.0000 0.3284 1.0147 -0.0389
4.0000 4.0000 0.9999 0.3136 0.7775 0.5695
-4.0000 -2.0000 -6.0000 0.1758 -0.5792 -0.7432
-0.0000 -2.0000 -11.0000 0.7822 -0.6223 -0.1568
3.0000 -2.0000 -8.0000 0.7006 -0.4758 0.4225
-3.0000 0.0000 -9.0000 0.5585 -0.3056 -0.7032
-1.0000 2.0000 11.0000 -0.8345 0.6000 -0.0156
1.0000 -1.0000 11.0000 -0.8680 0.1485 0.4349
0.0000 -1.0000 12.0000 -0.9998 0.1527 0.2831
-4.0000 1.0000 7.0000 -0.7194 0.2615 -0.5804
-3.0000 -4.0000 -5.0000 0.0565 -0.8611 -0.4797
-0.0000 -5.0000 -4.0000 0.0878 -0.9330 0.0935
2.0000 -5.0000 -3.0000 0.1129 -0.8618 0.4590
-4.0000 4.0000 1.0000 -0.1044 0.5987 -0.8100

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27419
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.713
_diffrn_reflns_theta_min         4.953
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -25.00   0.50    0.70    --  -49.12 -77.00 -90.00  180
  2  ω    -62.00  27.00   0.50    0.70    --  -49.12  19.00  60.00  178
  3  ω    -73.00  18.00   0.50    0.70    --  -49.12  77.00-150.00  182
  4  ω    -86.00   2.00   0.50    0.70    --  -70.00  57.00 -30.00  176
  5  ω    -88.00   2.00   0.50    0.70    --  -70.00 107.00  30.00  180
  6  ω    -83.00   6.00   0.50    0.70    --  -70.00  38.00-180.00  178
  7  ω   -115.00 -25.00   0.50    0.70    --  -49.12 -77.00 -30.00  180
  8  ω   -115.00 -25.00   0.50    0.70    --  -49.12 -77.00  90.00  180
  9  ω   -115.00 -25.00   0.50    0.70    --  -49.12 -77.00 120.00  180
 10  ω   -140.00 -82.00   0.50    0.70    --  -70.00 -99.00 120.00  116
 11  ω   -142.00 -54.00   0.50    0.70    --  -70.00 -57.00  30.00  176
 12  ω   -137.00 -71.00   0.50    0.70    --  -70.00 -77.00   0.00  132
 13  ω   -137.00 -46.00   0.50    0.70    --  -70.00 -77.00 -60.00  182
 14  ω   -115.00 -25.00   0.50    0.70    --  -49.12 -77.00-180.00  180
 15  ω   -137.00 -46.00   0.50    0.70    --  -70.00 -77.00-120.00  182
 16  ω     94.00 123.00   0.50    0.70    --  110.00 -19.00 -30.00   58
 17  ω     94.00 123.00   0.50    0.70    --  110.00 -19.00   0.00   58
 18  ω     94.00 123.00   0.50    0.70    --  110.00 -19.00  60.00   58
 19  ω     98.00 178.00   0.50    0.70    --  110.00  38.00   0.00  160
 20  ω    101.00 178.00   0.50    0.70    --  110.00 107.00  30.00  154
 21  ω     98.00 178.00   0.50    0.70    --  110.00  38.00 120.00  160
 22  ω     91.00 178.00   0.50    0.70    --  110.00 125.00   0.00  174
 23  ω     94.00 178.00   0.50    0.70    --  110.00  57.00 -60.00  168
 24  ω     98.00 178.00   0.50    0.70    --  110.00  38.00-180.00  160
 25  ω     94.00 123.00   0.50    0.70    --  110.00 -19.00-120.00   58
 26  ω     40.00 110.00   0.50    0.70    --  110.00 -99.00 -60.00  140
 27  ω     40.00 110.00   0.50    0.70    --  110.00 -99.00 -30.00  140
 28  ω     44.00 134.00   0.50    0.70    --  110.00 -77.00  60.00  180
 29  ω     39.00 122.00   0.50    0.70    --  110.00-125.00-120.00  166
 30  ω     40.00 110.00   0.50    0.70    --  110.00 -99.00  30.00  140
 31  ω     38.00  84.00   0.50    0.70    --  110.00 -57.00 -60.00   92
 32  ω     38.00  84.00   0.50    0.70    --  110.00 -57.00   0.00   92
 33  ω     38.00  84.00   0.50    0.70    --  110.00 -57.00  30.00   92
 34  ω     94.00 178.00   0.50    0.70    --  110.00  57.00  60.00  168
 35  ω     91.00 178.00   0.50    0.70    --  110.00 125.00-120.00  174
 36  ω     38.00  84.00   0.50    0.70    --  110.00 -57.00-180.00   92
 37  ω     39.00 122.00   0.50    0.70    --  110.00-125.00-180.00  166
;
_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      0.0522585000
_diffrn_orient_matrix_UB_12      0.0460197000
_diffrn_orient_matrix_UB_13      -0.0794800000
_diffrn_orient_matrix_UB_21      0.0223470000
_diffrn_orient_matrix_UB_22      0.1653927000
_diffrn_orient_matrix_UB_23      0.0265041000
_diffrn_orient_matrix_UB_31      0.1724369000
_diffrn_orient_matrix_UB_32      -0.0352268000
_diffrn_orient_matrix_UB_33      0.0206586000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2794
_reflns_number_total             2884
_reflns_odcompleteness_completeness 99.93
_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 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_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         0.298
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1137 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2884
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.100
_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)+(0.0466P)²+0.2258P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0820
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.93 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C9(H9)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.34438(12) 0.37214(12) 0.73863(6) 0.0270(2) Uani 1 1 d . . . . .
F2 F 0.22160(12) 0.22803(12) 0.64899(6) 0.0290(3) Uani 1 1 d . . . . .
F3 F 0.38775(14) 0.11643(12) 0.73256(6) 0.0318(3) Uani 1 1 d . . . . .
F4 F 0.37473(16) 0.72089(13) 0.40988(7) 0.0404(3) Uani 1 1 d . . . . .
N1 N 0.63882(17) 0.36077(16) 0.67988(8) 0.0206(3) Uani 1 1 d D . . . .
H1 H 0.589(2) 0.442(2) 0.7012(12) 0.025 Uiso 1 1 d DR . . . .
C1 C 0.4713(2) 0.39273(18) 0.56963(9) 0.0204(3) Uani 1 1 d . . . . .
C2 C 0.5353(2) 0.3841(2) 0.49755(9) 0.0237(4) Uani 1 1 d . . . . .
H2 H 0.600860 0.302953 0.485439 0.028 Uiso 1 1 calc R . . . .
C3 C 0.5839(2) 0.12952(19) 0.60189(10) 0.0228(3) Uani 1 1 d . . . . .
H3A H 0.671380 0.153385 0.568962 0.027 Uiso 1 1 calc R . . . .
H3B H 0.625008 0.071306 0.643691 0.027 Uiso 1 1 calc R . . . .
C4 C 0.3703(2) 0.51522(19) 0.58506(10) 0.0234(3) Uani 1 1 d . . . . .
H4 H 0.324186 0.522410 0.632165 0.028 Uiso 1 1 calc R . . . .
C5 C 0.5128(2) 0.27874(18) 0.63165(9) 0.0197(3) Uani 1 1 d . . . . .
C6 C 0.5032(2) 0.4937(2) 0.44361(10) 0.0265(4) Uani 1 1 d . . . . .
H6 H 0.546886 0.486714 0.395961 0.032 Uiso 1 1 calc R . . . .
C7 C 0.7008(2) 0.2732(2) 0.74774(10) 0.0266(4) Uani 1 1 d . . . . .
H7A H 0.665520 0.320156 0.793950 0.032 Uiso 1 1 calc R . . . .
H7B H 0.664764 0.168522 0.746695 0.032 Uiso 1 1 calc R . . . .
C8 C 0.4056(2) 0.6129(2) 0.46216(10) 0.0280(4) Uani 1 1 d . . . . .
C9 C 0.3375(2) 0.6261(2) 0.53183(10) 0.0276(4) Uani 1 1 d . . . . .
H9 H 0.271124 0.707148 0.542990 0.033 Uiso 1 1 calc R . . . .
C10 C 0.7820(2) 0.4213(2) 0.63913(11) 0.0275(4) Uani 1 1 d . . . . .
H10A H 0.812219 0.353777 0.598618 0.033 Uiso 1 1 calc R . . . .
H10B H 0.761480 0.521617 0.618763 0.033 Uiso 1 1 calc R . . . .
C11 C 0.9088(2) 0.4277(2) 0.69819(13) 0.0330(4) Uani 1 1 d . . . . .
H11A H 0.896605 0.516194 0.730117 0.040 Uiso 1 1 calc R . . . .
H11B H 1.013118 0.428668 0.675986 0.040 Uiso 1 1 calc R . . . .
C12 C 0.4648(2) 0.0319(2) 0.55921(11) 0.0283(4) Uani 1 1 d . . . . .
H12A H 0.424977 0.088029 0.517162 0.043 Uiso 1 1 calc GR . . . .
H12B H 0.379120 0.005427 0.591856 0.043 Uiso 1 1 calc GR . . . .
H12C H 0.515433 -0.059185 0.541834 0.043 Uiso 1 1 calc GR . . . .
C13 C 0.8789(2) 0.2807(3) 0.74126(12) 0.0369(5) Uani 1 1 d . . . . .
H13A H 0.919513 0.193575 0.714100 0.044 Uiso 1 1 calc R . . . .
H13B H 0.927702 0.284224 0.790348 0.044 Uiso 1 1 calc R . . . .
B1 B 0.3612(2) 0.2486(2) 0.68875(11) 0.0227(4) Uani 1 1 d . . . . .


_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 B1 1.412(2) . ?
F2 B1 1.392(2) . ?
F3 B1 1.419(2) . ?
F4 C8 1.357(2) . ?
N1 H1 0.910(18) . ?
N1 C5 1.551(2) . ?
N1 C7 1.529(2) . ?
N1 C10 1.512(2) . ?
C1 C2 1.399(2) . ?
C1 C4 1.403(2) . ?
C1 C5 1.535(2) . ?
C2 H2 0.9300 . ?
C2 C6 1.389(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C5 1.538(2) . ?
C3 C12 1.529(2) . ?
C4 H4 0.9300 . ?
C4 C9 1.389(2) . ?
C5 B1 1.662(2) . ?
C6 H6 0.9300 . ?
C6 C8 1.376(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C13 1.516(3) . ?
C8 C9 1.377(3) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.507(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C13 1.525(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C5 N1 H1 106.2(14) . . ?
C7 N1 H1 102.8(14) . . ?
C7 N1 C5 116.31(13) . . ?
C10 N1 H1 107.2(14) . . ?
C10 N1 C5 116.74(13) . . ?
C10 N1 C7 106.38(14) . . ?
C2 C1 C4 117.34(16) . . ?
C2 C1 C5 122.65(15) . . ?
C4 C1 C5 119.96(14) . . ?
C1 C2 H2 119.2 . . ?
C6 C2 C1 121.61(16) . . ?
C6 C2 H2 119.2 . . ?
H3A C3 H3B 107.8 . . ?
C5 C3 H3A 109.0 . . ?
C5 C3 H3B 109.0 . . ?
C12 C3 H3A 109.0 . . ?
C12 C3 H3B 109.0 . . ?
C12 C3 C5 113.07(15) . . ?
C1 C4 H4 119.1 . . ?
C9 C4 C1 121.75(16) . . ?
C9 C4 H4 119.1 . . ?
N1 C5 B1 105.48(13) . . ?
C1 C5 N1 104.80(12) . . ?
C1 C5 C3 113.41(13) . . ?
C1 C5 B1 111.67(14) . . ?
C3 C5 N1 108.55(13) . . ?
C3 C5 B1 112.29(14) . . ?
C2 C6 H6 120.7 . . ?
C8 C6 C2 118.62(16) . . ?
C8 C6 H6 120.7 . . ?
N1 C7 H7A 110.7 . . ?
N1 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C13 C7 N1 105.09(15) . . ?
C13 C7 H7A 110.7 . . ?
C13 C7 H7B 110.7 . . ?
F4 C8 C6 118.90(17) . . ?
F4 C8 C9 118.80(17) . . ?
C6 C8 C9 122.30(17) . . ?
C4 C9 H9 120.8 . . ?
C8 C9 C4 118.36(17) . . ?
C8 C9 H9 120.8 . . ?
N1 C10 H10A 110.9 . . ?
N1 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C11 C10 N1 104.45(15) . . ?
C11 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C10 C11 H11A 111.4 . . ?
C10 C11 H11B 111.4 . . ?
C10 C11 C13 101.68(16) . . ?
H11A C11 H11B 109.3 . . ?
C13 C11 H11A 111.4 . . ?
C13 C11 H11B 111.4 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 C11 103.95(16) . . ?
C7 C13 H13A 111.0 . . ?
C7 C13 H13B 111.0 . . ?
C11 C13 H13A 111.0 . . ?
C11 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?
F1 B1 F3 107.35(14) . . ?
F1 B1 C5 110.03(13) . . ?
F2 B1 F1 109.62(14) . . ?
F2 B1 F3 108.05(14) . . ?
F2 B1 C5 111.45(14) . . ?
F3 B1 C5 110.23(14) . . ?

_olex2_date_sample_data_collection 2017-09-20
_olex2_date_sample_submission    2017-09-19
_olex2_submission_original_sample_id jb190917_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.359
_oxdiff_exptl_absorpt_empirical_full_min 0.807
####################################################################### 
# 
# 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_jb110817_1_1_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1833581'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_audit_creation_date             2017-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H18 B F4 N), C1.5 H3 O0.5'
_chemical_formula_sum            'C35.50 H39 B2 F8 N2 O0.50'
_chemical_formula_weight         675.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         C37H34B2F10N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.15540(10)
_cell_length_b                   14.81710(10)
_cell_length_c                   24.1310(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.9310(10)
_cell_angle_gamma                90
_cell_volume                     3265.82(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31188
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.7270
_cell_measurement_theta_min      3.4860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.23a (Rigaku Oxford Diffraction, 2015)
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    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -6 -12 0.0407
0 -7 10 0.0540
1 8 -9 0.0542
-2 8 -7 0.0521
-5 4 0 0.0675
6 0 -4 0.0627
0 4 -14 0.0648
-5 -5 1 0.0760
0 6 12 0.0579
5 6 -1 0.0624
0 10 2 0.0509
1 7 11 0.0496
-6 -2 -1 0.0633
6 0 -1 0.0678
-5 3 -5 0.0522

_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.099
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
-0.0002 -5.9988 -11.9982 -0.9749 0.0113 0.1668
0.0001 -6.9996 9.9975 0.0475 0.9679 -0.0107
0.9997 7.9995 -8.9976 0.1030 -1.0020 0.1557
-1.9998 7.9992 -6.9979 0.0897 -0.9451 -0.3542
-4.9992 3.9992 0.0005 0.0683 -0.3634 -0.8641
5.9990 0.0006 -3.9994 0.0266 -0.1139 1.0198
-0.0002 4.0001 -13.9969 -0.4362 -0.8827 0.0769
-4.9992 -4.9998 0.9995 -0.4561 0.4093 -0.7764
0.0002 5.9988 11.9982 0.9749 -0.0113 -0.1668
4.9992 5.9997 -0.9995 0.5198 -0.4908 0.7657
0.0001 9.9987 2.0004 0.7362 -0.7349 -0.1240
1.0000 6.9988 10.9984 1.0266 -0.1250 -0.0046
-5.9991 -2.0001 -0.9998 -0.4009 0.0779 -0.9556
5.9991 0.0004 -1.0000 0.1747 0.0054 0.9941
-4.9993 2.9995 -4.9986 -0.2423 -0.4809 -0.8106

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7917
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.104
_diffrn_reflns_theta_min         3.503
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     85.00 173.00   0.50    0.50    --  107.75  77.00   0.00  176
  2  ω     91.00 178.00   0.50    0.50    --  107.75 125.00 150.00  174
  3  ω     95.00 178.00   0.50    0.50    --  107.75 119.00  81.00  166
  4  ω     97.00 178.00   0.50    0.50    --  107.75  19.00  90.00  162
  5  ω     98.00 178.00   0.50    0.50    --  107.75  38.00 150.00  160
  6  ω     97.00 178.00   0.50    0.50    --  107.75  19.00   0.00  162
  7  ω     85.00 173.00   0.50    0.50    --  107.75  77.00 -90.00  176
  8  ω     85.00 173.00   0.50    0.50    --  107.75  77.00-180.00  176
  9  ω     97.00 178.00   0.50    0.50    --  107.75  19.00-120.00  162
 10  ω     97.00 178.00   0.50    0.50    --  107.75  19.00 -90.00  162
 11  ω   -121.00   7.00   0.50    0.50    --  -50.21   0.00-150.00  256
 12  ω    -92.00  -5.00   0.50    0.50    --  -70.00  77.00 120.00  174
 13  ω    -85.00   1.00   0.50    0.50    --  -70.00  57.00-120.00  172
 14  ω    -60.00  25.00   0.50    0.50    --  -50.21  38.00-150.00  170
 15  ω     37.00  84.00   0.50    0.50    --  107.75 -57.00-120.00   94
 16  ω     37.00  84.00   0.50    0.50    --  107.75 -57.00 -60.00   94
 17  ω     43.00 130.00   0.50    0.50    --  107.75 -77.00  90.00  174
 18  ω   -141.00 -55.00   0.50    0.50    --  -70.00 -57.00 150.00  172
 19  ω   -141.00 -55.00   0.50    0.50    --  -70.00 -57.00  60.00  172
 20  ω   -141.00 -55.00   0.50    0.50    --  -70.00 -57.00 -30.00  172
 21  ω   -141.00 -55.00   0.50    0.50    --  -70.00 -57.00-120.00  172
 22  ω   -141.00 -55.00   0.50    0.50    --  -70.00 -57.00 -60.00  172
 23  ω   -121.00 -35.00   0.50    0.50    --  -50.21 -57.00   0.00  172
 24  ω   -141.00 -79.00   0.50    0.50    --  -70.00 -57.00 120.00  124
 25  ω   -121.00 -35.00   0.50    0.50    --  -50.21 -57.00  90.00  172
 26  ω     39.00 111.00   0.50    0.50    --  107.75 -99.00-120.00  144
 27  ω     38.00 121.00   0.50    0.50    --  107.75-125.00-150.00  166
 28  ω   -121.00 -35.00   0.50    0.50    --  -50.21 -57.00-180.00  172
 29  ω   -140.00 -75.00   0.50    0.50    --  -70.00-125.00-150.00  130
 30  ω   -139.00 -84.00   0.50    0.50    --  -70.00 -99.00 120.00  110
 31  ω     38.00 121.00   0.50    0.50    --  107.75-125.00 120.00  166
;
_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      0.0373498000
_diffrn_orient_matrix_UB_12      0.0637499000
_diffrn_orient_matrix_UB_13      0.0493806000
_diffrn_orient_matrix_UB_21      0.0075407000
_diffrn_orient_matrix_UB_22      -0.0814548000
_diffrn_orient_matrix_UB_23      0.0397848000
_diffrn_orient_matrix_UB_31      0.1642890000
_diffrn_orient_matrix_UB_32      -0.0106917000
_diffrn_orient_matrix_UB_33      -0.0085552000
_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              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          
;
Sample was twinned, hklf5 (one component) used
for final refinement.
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6750
_reflns_number_total             7917
_reflns_special_details          
;
 _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 1.171.39.23a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.23a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         7917
_refine_ls_number_restraints     154
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.062
_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)+(0.0640P)²+1.3423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1250
_refine_special_details          
;
BASF refined to 0.0905(19). Disorder in C6H5F units
(alternating para F position, 60:40 and 70:30 occ.).
1/2 acetone per a.u., disordered over inversion and
additionally over two positions by rotation around
central carbon. Additional disorder in one of the
pyrrolidine units (one CH2).
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9102(16)
 0.0898(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N1A-H1A = N1C-H1C
 0.93 with sigma of 0.02
 C2E-C1E = C2F-C1E = C3E-C1E = C3F-C1E
 1.5 with sigma of 0.02
 O1F-C1E \\sim O1E-C1E
 with sigma of 0.02
 C2E-C3E \\sim C2F-C3F
 with sigma of 0.02
 C3E-C1E \\sim C3F-C1E \\sim C2F-C1E \\sim C2E-C1E
 with sigma of 0.02
 C2A-C1A \\sim C3A-C2A \\sim C3A-C2B \\sim C2B-C1A
 with sigma of 0.02
4. Restrained planarity
 C1E, O1F, C2F, C3F
 with sigma of 0.1
 C1E, O1E, C2E, C3E
 with sigma of 0.1
5. Rigid bond restraints
 C1E, O1F, C2F, C3F, O1E, C2E, C3E
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Uiso/Uaniso restraints and constraints
Uanis(C3E) \\sim Ueq, Uanis(C3F) \\sim Ueq, Uanis(C1E) \\sim Ueq, Uanis(C2E)
\\sim Ueq, Uanis(C2F) \\sim Ueq, Uanis(O1E) \\sim Ueq, Uanis(O1F) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.01
7. Rigid body (RIGU) restrains
 C1E, O1F, C2F, C3F, O1E, C2E, C3E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1A, C1A, C3A, C4A, C2A, C2B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
8. Others
 Sof(H1AC)=Sof(H1AD)=Sof(H3AC)=Sof(H3AD)=Sof(H15A)=Sof(F1B)=Sof(C2B)=Sof(H2BA)=
 Sof(H2BB)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(H3AA)=Sof(H3AB)=Sof(H9A)=Sof(F1A)=Sof(C2A)=Sof(H2AA)=
 Sof(H2AB)=FVAR(1)
 Sof(H9C)=Sof(F1D)=1-FVAR(2)
 Sof(H15C)=Sof(F1C)=FVAR(2)
 Sof(O1F)=Sof(C2F)=Sof(H2FA)=Sof(H2FB)=Sof(H2FC)=Sof(C3F)=Sof(H3FA)=Sof(H3FB)=
 Sof(H3FC)=0.5*(1-FVAR(4))
 Sof(O1E)=Sof(C2E)=Sof(H2EA)=Sof(H2EB)=Sof(H2EC)=Sof(C3E)=Sof(H3EA)=Sof(H3EB)=
 Sof(H3EC)=0.5*FVAR(4)
 Fixed Sof: C1E(0.5)
9.a Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C1A(H1AC,H1AD), C3A(H3AA,H3AB), C3A(H3AC,H3AD), C4A(H4AA,
 H4AB), C2A(H2AA,H2AB), C2B(H2BA,H2BB), C1C(H1CA,H1CB), C2C(H2CA,H2CB),
 C3C(H3CA,H3CB), C4C(H4CA,H4CB)
9.b Me refined with riding coordinates:
 C2F(H2FA,H2FB,H2FC), C3F(H3FA,H3FB,H3FC), C2E(H2EA,H2EB,H2EC), C3E(H3EA,H3EB,
 H3EC)
9.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C17A(H17A), C7C(H7C), C8C(H8C), C9C(H9C), C10C(H10C),
 C11C(H11C), C13C(H13C), C14C(H14C), C15C(H15C), C16C(H16C), C17C(H17C)
;
_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
F3A F 0.61185(10) 0.67136(6) 0.62293(4) 0.0283(2) Uani 1 1 d . . . . .
F4A F 0.63326(10) 0.59347(6) 0.54274(4) 0.0306(2) Uani 1 1 d . . . . .
F5A F 0.73120(10) 0.73426(6) 0.55150(4) 0.0299(2) Uani 1 1 d . . . . .
N1A N 0.33299(14) 0.66532(8) 0.55993(5) 0.0244(3) Uani 1 1 d D U . . .
H1A H 0.360(2) 0.6526(13) 0.5962(6) 0.029 Uiso 1 1 d DR . . . .
C1A C 0.17569(18) 0.70024(12) 0.55784(7) 0.0314(4) Uani 1 1 d D U . . .
H1AA H 0.1363 0.6957 0.5949 0.038 Uiso 0.733(3) 1 calc R . P A 1
H1AB H 0.1719 0.7642 0.5460 0.038 Uiso 0.733(3) 1 calc R . P A 1
H1AC H 0.1485 0.7312 0.5223 0.038 Uiso 0.267(3) 1 calc R . P A 2
H1AD H 0.1606 0.7419 0.5890 0.038 Uiso 0.267(3) 1 calc R . P A 2
C3A C 0.1643(2) 0.54883(13) 0.52649(9) 0.0399(4) Uani 1 1 d D U . . .
H3AA H 0.1357 0.5200 0.5611 0.048 Uiso 0.733(3) 1 calc R . P A 1
H3AB H 0.1400 0.5080 0.4947 0.048 Uiso 0.733(3) 1 calc R . P A 1
H3AC H 0.1231 0.5556 0.4877 0.048 Uiso 0.267(3) 1 calc R . P A 2
H3AD H 0.1528 0.4851 0.5376 0.048 Uiso 0.267(3) 1 calc R . P A 2
C4A C 0.32511(18) 0.57404(10) 0.53043(7) 0.0287(3) Uani 1 1 d . U . . .
H4AA H 0.3623 0.5789 0.4930 0.034 Uiso 1 1 calc R . . . .
H4AB H 0.3837 0.5283 0.5520 0.034 Uiso 1 1 calc R . . . .
C5A C 0.45595(17) 0.72864(10) 0.54176(6) 0.0244(3) Uani 1 1 d . . . . .
C6A C 0.44970(18) 0.81754(10) 0.57379(6) 0.0255(3) Uani 1 1 d . . . . .
C7A C 0.39619(19) 0.82495(11) 0.62643(7) 0.0291(3) Uani 1 1 d . . . . .
H7A H 0.3533 0.7737 0.6426 0.035 Uiso 1 1 calc R . . . .
C8A C 0.4045(2) 0.90600(11) 0.65575(7) 0.0323(4) Uani 1 1 d . . . . .
H8A H 0.3662 0.9100 0.6913 0.039 Uiso 1 1 calc R . . . .
C9A C 0.4684(2) 0.98026(11) 0.63306(7) 0.0350(4) Uani 1 1 d . . . . .
H9A H 0.4743 1.0356 0.6530 0.042 Uiso 0.733(3) 1 calc R . P A 1
C10A C 0.5239(2) 0.97460(11) 0.58147(7) 0.0362(4) Uani 1 1 d . . . . .
H10A H 0.5683 1.0259 0.5660 0.043 Uiso 1 1 calc R . . . .
C11A C 0.5148(2) 0.89395(11) 0.55212(7) 0.0302(4) Uani 1 1 d . . . . .
H11A H 0.5535 0.8907 0.5166 0.036 Uiso 1 1 calc R . . . .
C12A C 0.43608(17) 0.74378(10) 0.47894(6) 0.0249(3) Uani 1 1 d . . . . .
C13A C 0.31898(18) 0.79440(11) 0.45541(6) 0.0281(3) Uani 1 1 d . . . . .
H13A H 0.2527 0.8215 0.4790 0.034 Uiso 1 1 calc R . . . .
C14A C 0.2969(2) 0.80610(11) 0.39830(7) 0.0319(4) Uani 1 1 d . . . . .
H14A H 0.2146 0.8387 0.3828 0.038 Uiso 1 1 calc R . . . .
C15A C 0.3968(2) 0.76958(12) 0.36479(7) 0.0340(4) Uani 1 1 d . . . . .
H15A H 0.3823 0.7771 0.3257 0.041 Uiso 0.267(3) 1 calc R . P A 2
C16A C 0.5174(2) 0.72225(12) 0.38626(7) 0.0338(4) Uani 1 1 d . . . . .
H16A H 0.5869 0.6992 0.3624 0.041 Uiso 1 1 calc R . . . .
C17A C 0.53574(19) 0.70875(11) 0.44329(7) 0.0296(3) Uani 1 1 d . . . . .
H17A H 0.6175 0.6751 0.4583 0.035 Uiso 1 1 calc R . . . .
B1A B 0.6141(2) 0.68035(12) 0.56399(7) 0.0255(4) Uani 1 1 d . . . . .
F1A F 0.37525(19) 0.77830(11) 0.31027(5) 0.0484(5) Uani 0.733(3) 1 d . . P A 1
C2A C 0.0896(3) 0.64343(16) 0.51742(10) 0.0335(6) Uani 0.733(3) 1 d D U P A 1
H2AA H 0.0973 0.6653 0.4790 0.040 Uiso 0.733(3) 1 calc R . P A 1
H2AB H -0.0149 0.6415 0.5256 0.040 Uiso 0.733(3) 1 calc R . P A 1
F1B F 0.4810(5) 1.0550(2) 0.66198(15) 0.0366(11) Uani 0.267(3) 1 d . . P A 2
C2B C 0.0856(8) 0.6083(4) 0.5634(3) 0.0418(17) Uani 0.267(3) 1 d D U P A 2
H2BA H 0.0918 0.5857 0.6021 0.050 Uiso 0.267(3) 1 calc R . P A 2
H2BB H -0.0185 0.6156 0.5502 0.050 Uiso 0.267(3) 1 calc R . P A 2
F3C F 0.19836(10) 0.52551(7) 0.72900(4) 0.0371(2) Uani 1 1 d . . . . .
F4C F 0.31620(11) 0.46616(6) 0.65702(4) 0.0353(2) Uani 1 1 d . . . . .
F5C F 0.32431(10) 0.61672(6) 0.67212(4) 0.0298(2) Uani 1 1 d . . . . .
N1C N 0.60128(14) 0.54384(9) 0.70594(6) 0.0264(3) Uani 1 1 d D . . . .
H1C H 0.574(2) 0.5925(12) 0.6833(7) 0.032 Uiso 1 1 d DR . . . .
C1C C 0.74968(18) 0.56877(13) 0.73464(8) 0.0361(4) Uani 1 1 d . . . . .
H1CA H 0.7817 0.6289 0.7223 0.043 Uiso 1 1 calc R . . . .
H1CB H 0.7447 0.5696 0.7755 0.043 Uiso 1 1 calc R . . . .
C2C C 0.8535(2) 0.49592(17) 0.71742(9) 0.0490(5) Uani 1 1 d . . . . .
H2CA H 0.8510 0.4426 0.7421 0.059 Uiso 1 1 calc R . . . .
H2CB H 0.9552 0.5187 0.7178 0.059 Uiso 1 1 calc R . . . .
C3C C 0.7936(2) 0.47324(15) 0.65864(8) 0.0428(4) Uani 1 1 d . . . . .
H3CA H 0.8175 0.5210 0.6320 0.051 Uiso 1 1 calc R . . . .
H3CB H 0.8318 0.4147 0.6461 0.051 Uiso 1 1 calc R . . . .
C4C C 0.63093(19) 0.46865(11) 0.66527(7) 0.0321(4) Uani 1 1 d . . . . .
H4CA H 0.6036 0.4093 0.6802 0.039 Uiso 1 1 calc R . . . .
H4CB H 0.5750 0.4785 0.6292 0.039 Uiso 1 1 calc R . . . .
C5C C 0.47146(17) 0.52538(10) 0.74234(6) 0.0255(3) Uani 1 1 d . . . . .
C6C C 0.45991(18) 0.60398(11) 0.78284(7) 0.0294(3) Uani 1 1 d . . . . .
C7C C 0.4935(2) 0.69302(12) 0.76909(8) 0.0356(4) Uani 1 1 d . . . . .
H7C H 0.5352 0.7051 0.7349 0.043 Uiso 1 1 calc R . . . .
C8C C 0.4669(2) 0.76414(13) 0.80469(9) 0.0444(5) Uani 1 1 d . . . . .
H8C H 0.4903 0.8242 0.7947 0.053 Uiso 1 1 calc R . . . .
C9C C 0.4072(2) 0.74760(14) 0.85393(9) 0.0477(5) Uani 1 1 d . . . . .
H9C H 0.3910 0.7963 0.8783 0.057 Uiso 0.395(3) 1 calc R . P B 2
C10C C 0.3701(2) 0.66139(15) 0.86876(9) 0.0478(5) Uani 1 1 d . . . . .
H10C H 0.3270 0.6505 0.9028 0.057 Uiso 1 1 calc R . . . .
C11C C 0.3967(2) 0.59006(13) 0.83305(8) 0.0378(4) Uani 1 1 d . . . . .
H11C H 0.3710 0.5305 0.8432 0.045 Uiso 1 1 calc R . . . .
C12C C 0.49550(18) 0.43498(11) 0.77228(7) 0.0276(3) Uani 1 1 d . . . . .
C13C C 0.6074(2) 0.42360(12) 0.81422(7) 0.0347(4) Uani 1 1 d . . . . .
H13C H 0.6672 0.4737 0.8253 0.042 Uiso 1 1 calc R . . . .
C14C C 0.6330(2) 0.34047(13) 0.84000(8) 0.0410(4) Uani 1 1 d . . . . .
H14C H 0.7113 0.3333 0.8676 0.049 Uiso 1 1 calc R . . . .
C15C C 0.5431(2) 0.26883(12) 0.82501(8) 0.0409(4) Uani 1 1 d . . . . .
H15C H 0.5600 0.2120 0.8426 0.049 Uiso 0.605(3) 1 calc R . P B 1
C16C C 0.4292(2) 0.27780(12) 0.78506(8) 0.0385(4) Uani 1 1 d . . . . .
H16C H 0.3670 0.2281 0.7756 0.046 Uiso 1 1 calc R . . . .
C17C C 0.40646(19) 0.36111(11) 0.75861(7) 0.0310(3) Uani 1 1 d . . . . .
H17C H 0.3286 0.3674 0.7307 0.037 Uiso 1 1 calc R . . . .
B1C B 0.3216(2) 0.53095(12) 0.69926(8) 0.0273(4) Uani 1 1 d . . . . .
F1C F 0.3906(2) 0.81628(14) 0.89020(9) 0.0594(7) Uani 0.605(3) 1 d . . P B 1
F1D F 0.5521(3) 0.18455(16) 0.84618(11) 0.0378(8) Uani 0.395(3) 1 d . . P B 2
C1E C 0.0197(7) 0.9888(5) 0.5048(3) 0.0665(14) Uani 0.5 1 d D U P . .
O1F O 0.0835(11) 0.9534(6) 0.5450(4) 0.047(3) Uani 0.182(6) 1 d D U P C -2
C2F C -0.1507(9) 0.9729(6) 0.4874(5) 0.028(2) Uani 0.182(6) 1 d D U P C -2
H2FA H -0.1780 0.9112 0.4971 0.042 Uiso 0.182(6) 1 calc R . P C -2
H2FB H -0.2094 1.0160 0.5072 0.042 Uiso 0.182(6) 1 calc R . P C -2
H2FC H -0.1688 0.9818 0.4473 0.042 Uiso 0.182(6) 1 calc R . P C -2
C3F C 0.054(2) 1.0744(9) 0.4713(7) 0.044(4) Uani 0.182(6) 1 d D U P C -2
H3FA H 0.1607 1.0810 0.4704 0.067 Uiso 0.182(6) 1 calc R . P C -2
H3FB H 0.0102 1.0688 0.4333 0.067 Uiso 0.182(6) 1 calc R . P C -2
H3FC H 0.0142 1.1275 0.4891 0.067 Uiso 0.182(6) 1 calc R . P C -2
O1E O 0.1216(7) 0.9382(4) 0.5109(4) 0.080(3) Uani 0.318(6) 1 d D U P C -1
C2E C -0.1317(9) 0.9671(5) 0.5197(5) 0.052(2) Uani 0.318(6) 1 d D U P C -1
H2EA H -0.1290 0.9148 0.5446 0.078 Uiso 0.318(6) 1 calc R . P C -1
H2EB H -0.1727 1.0190 0.5384 0.078 Uiso 0.318(6) 1 calc R . P C -1
H2EC H -0.1931 0.9532 0.4859 0.078 Uiso 0.318(6) 1 calc R . P C -1
C3E C 0.0325(9) 1.0894(5) 0.4855(4) 0.0342(19) Uani 0.318(6) 1 d D U P C -1
H3EA H 0.1331 1.1106 0.4935 0.051 Uiso 0.318(6) 1 calc R . P C -1
H3EB H 0.0070 1.0935 0.4454 0.051 Uiso 0.318(6) 1 calc R . P C -1
H3EC H -0.0346 1.1271 0.5054 0.051 Uiso 0.318(6) 1 calc R . P C -1


_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
F3A B1A 1.4299(19) . ?
F4A B1A 1.4013(19) . ?
F5A B1A 1.387(2) . ?
N1A H1A 0.914(15) . ?
N1A C1A 1.528(2) . ?
N1A C4A 1.5278(19) . ?
N1A C5A 1.552(2) . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1A H1AC 0.9900 . ?
C1A H1AD 0.9900 . ?
C1A C2A 1.475(3) . ?
C1A C2B 1.603(7) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A H3AC 0.9900 . ?
C3A H3AD 0.9900 . ?
C3A C4A 1.515(2) . ?
C3A C2A 1.569(3) . ?
C3A C2B 1.476(7) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A C6A 1.530(2) . ?
C5A C12A 1.531(2) . ?
C5A B1A 1.670(2) . ?
C6A C7A 1.397(2) . ?
C6A C11A 1.397(2) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.393(2) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.377(3) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.379(3) . ?
C9A F1B 1.310(4) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.389(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.397(2) . ?
C12A C17A 1.396(2) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.390(2) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.372(3) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.379(3) . ?
C15A F1A 1.323(2) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.390(2) . ?
C17A H17A 0.9500 . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
F3C B1C 1.381(2) . ?
F4C B1C 1.399(2) . ?
F5C B1C 1.4307(19) . ?
N1C H1C 0.928(15) . ?
N1C C1C 1.527(2) . ?
N1C C4C 1.522(2) . ?
N1C C5C 1.550(2) . ?
C1C H1CA 0.9900 . ?
C1C H1CB 0.9900 . ?
C1C C2C 1.515(3) . ?
C2C H2CA 0.9900 . ?
C2C H2CB 0.9900 . ?
C2C C3C 1.523(3) . ?
C3C H3CA 0.9900 . ?
C3C H3CB 0.9900 . ?
C3C C4C 1.510(3) . ?
C4C H4CA 0.9900 . ?
C4C H4CB 0.9900 . ?
C5C C6C 1.529(2) . ?
C5C C12C 1.531(2) . ?
C5C B1C 1.665(2) . ?
C6C C7C 1.400(2) . ?
C6C C11C 1.394(3) . ?
C7C H7C 0.9500 . ?
C7C C8C 1.392(3) . ?
C8C H8C 0.9500 . ?
C8C C9C 1.364(3) . ?
C9C H9C 0.9500 . ?
C9C C10C 1.375(3) . ?
C9C F1C 1.357(3) . ?
C10C H10C 0.9500 . ?
C10C C11C 1.395(3) . ?
C11C H11C 0.9500 . ?
C12C C13C 1.400(2) . ?
C12C C17C 1.391(2) . ?
C13C H13C 0.9500 . ?
C13C C14C 1.392(2) . ?
C14C H14C 0.9500 . ?
C14C C15C 1.376(3) . ?
C15C H15C 0.9500 . ?
C15C C16C 1.377(3) . ?
C15C F1D 1.350(3) . ?
C16C H16C 0.9500 . ?
C16C C17C 1.399(2) . ?
C17C H17C 0.9500 . ?
C1E C1E 0.531(10) 3_576 ?
C1E O1F 1.217(9) . ?
C1E C2F 1.605(9) . ?
C1E C3F 1.548(11) . ?
C1E O1E 1.198(7) . ?
C1E C2E 1.492(9) . ?
C1E C3E 1.569(8) . ?
C2F H2FA 0.9800 . ?
C2F H2FB 0.9800 . ?
C2F H2FC 0.9800 . ?
C3F H3FA 0.9800 . ?
C3F H3FB 0.9800 . ?
C3F H3FC 0.9800 . ?
C2E H2EA 0.9800 . ?
C2E H2EB 0.9800 . ?
C2E H2EC 0.9800 . ?
C3E H3EA 0.9800 . ?
C3E H3EB 0.9800 . ?
C3E H3EC 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
C1A N1A H1A 107.2(12) . . ?
C1A N1A C5A 119.10(12) . . ?
C4A N1A H1A 105.4(12) . . ?
C4A N1A C1A 105.67(12) . . ?
C4A N1A C5A 114.56(12) . . ?
C5A N1A H1A 103.9(12) . . ?
N1A C1A H1AA 110.4 . . ?
N1A C1A H1AB 110.4 . . ?
N1A C1A H1AC 111.5 . . ?
N1A C1A H1AD 111.5 . . ?
N1A C1A C2B 101.5(3) . . ?
H1AA C1A H1AB 108.6 . . ?
H1AC C1A H1AD 109.3 . . ?
C2A C1A N1A 106.76(15) . . ?
C2A C1A H1AA 110.4 . . ?
C2A C1A H1AB 110.4 . . ?
C2B C1A H1AC 111.5 . . ?
C2B C1A H1AD 111.5 . . ?
H3AA C3A H3AB 109.3 . . ?
H3AC C3A H3AD 108.3 . . ?
C4A C3A H3AA 111.4 . . ?
C4A C3A H3AB 111.4 . . ?
C4A C3A H3AC 109.9 . . ?
C4A C3A H3AD 109.9 . . ?
C4A C3A C2A 101.61(15) . . ?
C2A C3A H3AA 111.4 . . ?
C2A C3A H3AB 111.4 . . ?
C2B C3A H3AC 109.9 . . ?
C2B C3A H3AD 109.9 . . ?
C2B C3A C4A 109.1(3) . . ?
N1A C4A H4AA 110.7 . . ?
N1A C4A H4AB 110.7 . . ?
C3A C4A N1A 105.20(13) . . ?
C3A C4A H4AA 110.7 . . ?
C3A C4A H4AB 110.7 . . ?
H4AA C4A H4AB 108.8 . . ?
N1A C5A B1A 106.25(11) . . ?
C6A C5A N1A 108.95(12) . . ?
C6A C5A C12A 111.59(12) . . ?
C6A C5A B1A 105.55(12) . . ?
C12A C5A N1A 109.22(12) . . ?
C12A C5A B1A 114.99(13) . . ?
C7A C6A C5A 123.68(14) . . ?
C7A C6A C11A 117.49(14) . . ?
C11A C6A C5A 118.48(14) . . ?
C6A C7A H7A 119.4 . . ?
C8A C7A C6A 121.27(15) . . ?
C8A C7A H7A 119.4 . . ?
C7A C8A H8A 120.1 . . ?
C9A C8A C7A 119.78(16) . . ?
C9A C8A H8A 120.1 . . ?
C8A C9A H9A 119.9 . . ?
C8A C9A C10A 120.21(15) . . ?
C10A C9A H9A 119.9 . . ?
F1B C9A C8A 119.2(2) . . ?
F1B C9A C10A 120.5(2) . . ?
C9A C10A H10A 120.0 . . ?
C9A C10A C11A 119.99(16) . . ?
C11A C10A H10A 120.0 . . ?
C6A C11A H11A 119.4 . . ?
C10A C11A C6A 121.24(16) . . ?
C10A C11A H11A 119.4 . . ?
C13A C12A C5A 121.14(14) . . ?
C17A C12A C5A 121.15(14) . . ?
C17A C12A C13A 117.70(14) . . ?
C12A C13A H13A 119.2 . . ?
C14A C13A C12A 121.70(16) . . ?
C14A C13A H13A 119.2 . . ?
C13A C14A H14A 120.7 . . ?
C15A C14A C13A 118.53(16) . . ?
C15A C14A H14A 120.7 . . ?
C14A C15A H15A 119.1 . . ?
C14A C15A C16A 121.87(15) . . ?
C16A C15A H15A 119.1 . . ?
F1A C15A C14A 119.18(17) . . ?
F1A C15A C16A 118.93(17) . . ?
C15A C16A H16A 120.5 . . ?
C15A C16A C17A 118.97(16) . . ?
C17A C16A H16A 120.5 . . ?
C12A C17A H17A 119.4 . . ?
C16A C17A C12A 121.14(16) . . ?
C16A C17A H17A 119.4 . . ?
F3A B1A C5A 106.77(13) . . ?
F4A B1A F3A 106.80(12) . . ?
F4A B1A C5A 113.82(13) . . ?
F5A B1A F3A 109.50(12) . . ?
F5A B1A F4A 109.34(14) . . ?
F5A B1A C5A 110.46(13) . . ?
C1A C2A C3A 102.08(17) . . ?
C1A C2A H2AA 111.4 . . ?
C1A C2A H2AB 111.4 . . ?
C3A C2A H2AA 111.4 . . ?
C3A C2A H2AB 111.4 . . ?
H2AA C2A H2AB 109.2 . . ?
C1A C2B H2BA 111.7 . . ?
C1A C2B H2BB 111.7 . . ?
C3A C2B C1A 100.4(4) . . ?
C3A C2B H2BA 111.7 . . ?
C3A C2B H2BB 111.7 . . ?
H2BA C2B H2BB 109.5 . . ?
C1C N1C H1C 106.0(12) . . ?
C1C N1C C5C 118.59(12) . . ?
C4C N1C H1C 104.0(12) . . ?
C4C N1C C1C 106.09(13) . . ?
C4C N1C C5C 114.45(12) . . ?
C5C N1C H1C 106.4(12) . . ?
N1C C1C H1CA 110.7 . . ?
N1C C1C H1CB 110.7 . . ?
H1CA C1C H1CB 108.8 . . ?
C2C C1C N1C 104.99(15) . . ?
C2C C1C H1CA 110.7 . . ?
C2C C1C H1CB 110.7 . . ?
C1C C2C H2CA 111.2 . . ?
C1C C2C H2CB 111.2 . . ?
C1C C2C C3C 102.70(15) . . ?
H2CA C2C H2CB 109.1 . . ?
C3C C2C H2CA 111.2 . . ?
C3C C2C H2CB 111.2 . . ?
C2C C3C H3CA 111.4 . . ?
C2C C3C H3CB 111.4 . . ?
H3CA C3C H3CB 109.3 . . ?
C4C C3C C2C 101.91(15) . . ?
C4C C3C H3CA 111.4 . . ?
C4C C3C H3CB 111.4 . . ?
N1C C4C H4CA 110.8 . . ?
N1C C4C H4CB 110.8 . . ?
C3C C4C N1C 104.84(14) . . ?
C3C C4C H4CA 110.8 . . ?
C3C C4C H4CB 110.8 . . ?
H4CA C4C H4CB 108.9 . . ?
N1C C5C B1C 105.57(12) . . ?
C6C C5C N1C 108.50(12) . . ?
C6C C5C C12C 112.26(13) . . ?
C6C C5C B1C 105.73(13) . . ?
C12C C5C N1C 109.33(12) . . ?
C12C C5C B1C 115.06(13) . . ?
C7C C6C C5C 122.71(15) . . ?
C11C C6C C5C 119.62(15) . . ?
C11C C6C C7C 117.19(16) . . ?
C6C C7C H7C 119.4 . . ?
C8C C7C C6C 121.10(18) . . ?
C8C C7C H7C 119.4 . . ?
C7C C8C H8C 120.0 . . ?
C9C C8C C7C 119.96(19) . . ?
C9C C8C H8C 120.0 . . ?
C8C C9C H9C 119.5 . . ?
C8C C9C C10C 120.96(18) . . ?
C10C C9C H9C 119.5 . . ?
F1C C9C C8C 119.7(2) . . ?
F1C C9C C10C 119.2(2) . . ?
C9C C10C H10C 120.5 . . ?
C9C C10C C11C 119.1(2) . . ?
C11C C10C H10C 120.5 . . ?
C6C C11C C10C 121.68(18) . . ?
C6C C11C H11C 119.2 . . ?
C10C C11C H11C 119.2 . . ?
C13C C12C C5C 121.41(15) . . ?
C17C C12C C5C 120.91(14) . . ?
C17C C12C C13C 117.68(15) . . ?
C12C C13C H13C 119.3 . . ?
C14C C13C C12C 121.46(18) . . ?
C14C C13C H13C 119.3 . . ?
C13C C14C H14C 120.5 . . ?
C15C C14C C13C 119.06(18) . . ?
C15C C14C H14C 120.5 . . ?
C14C C15C H15C 119.3 . . ?
C14C C15C C16C 121.32(16) . . ?
C16C C15C H15C 119.3 . . ?
F1D C15C C14C 126.5(2) . . ?
F1D C15C C16C 112.2(2) . . ?
C15C C16C H16C 120.4 . . ?
C15C C16C C17C 119.12(18) . . ?
C17C C16C H16C 120.4 . . ?
C12C C17C C16C 121.31(17) . . ?
C12C C17C H17C 119.3 . . ?
C16C C17C H17C 119.3 . . ?
F3C B1C F4C 110.44(14) . . ?
F3C B1C F5C 109.27(13) . . ?
F3C B1C C5C 109.90(13) . . ?
F4C B1C F5C 106.09(13) . . ?
F4C B1C C5C 114.04(14) . . ?
F5C B1C C5C 106.88(13) . . ?
C1E C1E O1F 153(2) 3_576 . ?
C1E C1E C2F 50.2(15) 3_576 . ?
C1E C1E C3F 54.5(15) 3_576 . ?
C1E C1E O1E 161(2) 3_576 . ?
C1E C1E C2E 68.0(15) 3_576 . ?
C1E C1E C3E 48.6(15) 3_576 . ?
O1F C1E C2F 123.4(8) . . ?
O1F C1E C3F 131.6(10) . . ?
C3F C1E C2F 102.4(8) . . ?
O1E C1E C2E 124.3(7) . . ?
O1E C1E C3E 123.9(7) . . ?
C2E C1E C3E 111.5(5) . . ?
C1E C2F H2FA 109.5 . . ?
C1E C2F H2FB 109.5 . . ?
C1E C2F H2FC 109.5 . . ?
H2FA C2F H2FB 109.5 . . ?
H2FA C2F H2FC 109.5 . . ?
H2FB C2F H2FC 109.5 . . ?
C1E C3F H3FA 109.5 . . ?
C1E C3F H3FB 109.5 . . ?
C1E C3F H3FC 109.5 . . ?
H3FA C3F H3FB 109.5 . . ?
H3FA C3F H3FC 109.5 . . ?
H3FB C3F H3FC 109.5 . . ?
C1E C2E H2EA 109.5 . . ?
C1E C2E H2EB 109.5 . . ?
C1E C2E H2EC 109.5 . . ?
H2EA C2E H2EB 109.5 . . ?
H2EA C2E H2EC 109.5 . . ?
H2EB C2E H2EC 109.5 . . ?
C1E C3E H3EA 109.5 . . ?
C1E C3E H3EB 109.5 . . ?
C1E C3E H3EC 109.5 . . ?
H3EA C3E H3EB 109.5 . . ?
H3EA C3E H3EC 109.5 . . ?
H3EB C3E H3EC 109.5 . . ?

_olex2_submission_original_sample_id jb110817_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.786
_oxdiff_exptl_absorpt_empirical_full_min 0.664
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.9102(16) 61320 2563 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.0898(16) 0 2563 nmt -0.9601 0.1645 0.0139 -0.4267 -0.9641 0.0175 0.4674
-0.0022 0.9959

_twin_special_details            
;
Component 2 rotated by -164.5603° 
 around [0.01 0.01 1.00] (reciprocal) or [0.23 0.02 0.97] (direct)
;
####################################################################### 
# 
# 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_jb120817_1_1
_database_code_depnum_ccdc_archive 'CCDC 1833582'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_audit_creation_date             2017-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 B F4 N'
_chemical_formula_sum            'C11 H14 B F4 N'
_chemical_formula_weight         247.04
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H28B2F8N2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.85970(10)
_cell_length_b                   11.13680(10)
_cell_length_c                   19.4080(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2347.25(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    55936
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.5940
_cell_measurement_theta_min      4.4830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.092
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.530
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28c (Rigaku Oxford Diffraction, 2015)
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    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 6 -5 0.0522
-6 4 0 0.0630
-4 -3 9 0.0849
0 -5 9 0.0471
6 1 -8 0.0954
6 -3 -1 0.1056
1 2 12 0.0636
-5 -4 4 0.0829
5 4 -3 0.0746
-1 -6 -5 0.0640
4 4 -6 0.0741
1 -7 1 0.0605
7 0 3 0.0818
0 -1 12 0.0582
0 4 11 0.0621
6 4 2 0.0780
-6 1 -6 0.0872
5 5 -2 0.0685
1 6 6 0.0667
-2 5 9 0.0557

_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.131
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
-3.0000 6.0000 -5.0000 -0.6226 -0.7992 -0.0126
-6.0000 4.0000 -0.0000 -0.4576 -0.6793 0.5990
-4.0000 -3.0000 9.0000 0.2036 0.3106 0.9314
0.0000 -5.0000 9.0000 0.4217 0.7357 0.5192
6.0000 1.0000 -8.0000 0.0103 0.0022 -1.0712
6.0000 -3.0000 -1.0000 0.3528 0.5791 -0.6653
1.0000 2.0000 12.0000 -0.5794 0.7060 0.4120
-5.0000 -4.0000 4.0000 0.4730 -0.0266 0.8287
5.0000 4.0000 -3.0000 -0.4987 0.0852 -0.7818
-1.0000 -6.0000 -5.0000 0.9219 -0.1292 -0.0060
4.0000 4.0000 -6.0000 -0.4110 -0.1762 -0.8099
1.0000 -7.0000 1.0000 0.8771 0.4352 0.0695
7.0000 0.0000 3.0000 -0.1520 0.7744 -0.6482
0.0000 -1.0000 12.0000 -0.1772 0.7453 0.5827
0.0000 4.0000 11.0000 -0.8040 0.4787 0.4391
6.0000 4.0000 2.0000 -0.6376 0.4639 -0.6597
-6.0000 1.0000 -6.0000 0.0877 -0.9064 0.3753
5.0000 5.0000 -2.0000 -0.6548 0.1023 -0.7541
1.0000 6.0000 6.0000 -0.9475 0.1878 0.0530
-2.0000 5.0000 9.0000 -0.8618 0.1489 0.5513

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            89056
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.169
_diffrn_reflns_theta_min         4.557
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_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    -96.00 -27.00   0.50    0.10    --  -26.00 161.00  50.74  138
  2  ω    -48.00 -22.00   0.50    0.10    --   14.00 151.00 -48.85   52
  3  ω    -51.00  40.00   0.50    0.10    --  -26.00  82.00-128.81  182
  4  ω    -95.00  -9.00   0.50    0.10    --  -70.00 125.00-180.00  172
  5  ω     -7.00  22.00   0.50    0.10    --   26.00  99.00-128.12   58
  6  ω     85.00 167.00   0.50    0.10    --  107.75  77.00-150.00  164
  7  ω     87.00 173.00   0.50    0.10    --  107.75  72.00  -1.00  172
  8  ω     99.00 125.00   0.50    0.10    --  107.75  38.00  60.00   52
  9  ω    153.00 178.00   0.50    0.10    --  107.75  38.00  60.00   50
 10  ω     59.00 120.00   0.50    0.10    --   50.21 178.00  90.00  122
 11  ω     15.00  44.00   0.50    0.10    --   38.00  79.00 -97.92   58
 12  ω    -73.00  15.00   0.50    0.10    --  -50.21  77.00  90.00  176
 13  ω     15.00  44.00   0.50    0.10    --   38.00  79.00 100.99   58
 14  ω     29.00 117.00   0.50    0.10    --   50.00  73.00  31.39  176
 15  ω     37.00  83.00   0.50    0.10    --  107.75 -57.00   0.00   92
 16  ω     46.00  72.00   0.50    0.10    --  107.75 -77.00 -30.00   52
 17  ω    103.00 130.00   0.50    0.10    --  107.75 -77.00 -30.00   54
 18  ω   -137.00 -50.00   0.50    0.10    --  -70.00 -71.00 143.24  174
 19  ω   -137.00 -50.00   0.50    0.10    --  -70.00 -71.00 -47.98  174
 20  ω   -138.00 -51.00   0.50    0.10    --  -70.00 -67.00-176.29  174
 21  ω     40.00 125.00   0.50    0.10    --   50.21  38.00-180.00  170
 22  ω     34.00 121.00   0.50    0.10    --   54.00  72.00 -52.36  174
 23  ω     38.00 125.00   0.50    0.10    --   58.00  72.00 142.87  174
 24  ω     38.00 125.00   0.50    0.10    --   58.00  72.00-163.41  174
 25  ω     38.00 125.00   0.50    0.10    --   58.00  72.00-110.48  174
 26  ω     42.00 130.00   0.50    0.10    --   62.00  70.00 -69.80  176
 27  ω     46.00 133.00   0.50    0.10    --   66.00  72.00  49.83  174
 28  ω     45.00 133.00   0.50    0.10    --   66.00  73.00-145.21  176
 29  ω     49.00 137.00   0.50    0.10    --   70.00  73.00 -61.66  176
 30  ω     53.00 141.00   0.50    0.10    --   74.00  73.00  97.92  176
 31  ω     53.00 141.00   0.50    0.10    --   74.00  73.00 -51.83  176
 32  ω     55.00 142.00   0.50    0.10    --   74.00  69.00 -18.54  174
 33  ω     64.00 151.00   0.50    0.10    --   82.00  65.00 115.35  174
 34  ω     68.00  95.00   0.50    0.10    --   82.00  58.00   6.21   54
 35  ω     70.00 114.00   0.50    0.10    --   86.00  60.00-170.53   88
 36  ω     93.00 127.00   0.50    0.10    --  107.75  57.00-150.00   68
 37  ω     85.00 173.00   0.50    0.10    --  107.75  77.00  30.00  176
 38  ω     85.00 172.00   0.50    0.10    --  107.75  77.00-120.00  174
 39  ω    122.00 173.00   0.50    0.10    --  107.75  77.00  90.00  102
 40  ω     85.00 117.00   0.50    0.10    --  107.75  77.00  90.00   64
 41  ω     86.00 171.00   0.50    0.10    --  107.75  77.00 -60.00  170
 42  ω    146.00 173.00   0.50    0.10    --  107.75  77.00 -90.00   54
 43  ω    132.00 171.00   0.50    0.10    --  107.75  71.00-175.22   78
 44  ω     86.00 131.00   0.50    0.10    --  107.75  77.00 -90.00   90
 45  ω    134.00 160.00   0.50    0.10    --  107.75  77.00   0.00   52
 46  ω    109.00 138.00   0.50    0.10    --  107.75  38.00 -90.00   58
 47  ω    143.00 174.00   0.50    0.10    --  107.75  38.00 -90.00   62
 48  ω     88.00 117.00   0.50    0.10    --  107.75  71.00-175.22   58
 49  ω     85.00 111.00   0.50    0.10    --  107.75  77.00   0.00   52
 50  ω    118.00 167.00   0.50    0.10    --  107.75  77.00 120.00   98
 51  ω     85.00 113.00   0.50    0.10    --  107.75  77.00 120.00   56
 52  ω     85.00 173.00   0.50    0.10    --  107.75  77.00  60.00  176
 53  ω     94.00 171.00   0.50    0.10    --  107.75  57.00 150.00  154
 54  ω     97.00 130.00   0.50    0.10    --  107.75  57.00 120.00   66
 55  ω     98.00 144.00   0.50    0.10    --  107.75  57.00-180.00   92
 56  ω     86.00 173.00   0.50    0.10    --  107.75  77.00 -30.00  174
 57  ω     94.00 119.00   0.50    0.10    --  107.75-125.00-180.00   50
 58  ω     62.00  87.00   0.50    0.10    --  107.75-125.00-180.00   50
 59  ω     46.00  76.00   0.50    0.10    --  107.75 -99.00-180.00   60
 60  ω     39.00 109.00   0.50    0.10    --  107.75 -99.00  30.00  140
 61  ω     40.00 106.00   0.50    0.10    --  107.75 -99.00 120.00  132
 62  ω     41.00  67.00   0.50    0.10    --  107.75 -99.00 -60.00   52
 63  ω     45.00 110.00   0.50    0.10    --  107.75 -99.00-150.00  130
 64  ω     40.00  85.00   0.50    0.10    --  107.75 -99.00-120.00   90
 65  ω     59.00 121.00   0.50    0.10    --  107.75-125.00   0.00  124
 66  ω     86.00 111.00   0.50    0.10    --  107.75 -99.00 -60.00   50
 67  ω   -125.00 -40.00   0.50    0.10    --  -50.21 -19.00 150.00  170
 68  ω   -137.00 -49.00   0.50    0.10    --  -70.00 -72.00  45.93  176
 69  ω   -138.00 -51.00   0.50    0.10    --  -70.00 -69.00  94.84  174
 70  ω   -137.00 -50.00   0.50    0.10    --  -70.00 -70.00-118.44  174
 71  ω   -138.00 -51.00   0.50    0.10    --  -70.00 -68.00   3.58  174
 72  ω   -136.00 -49.00   0.50    0.10    --  -70.00 -73.00 169.70  174
 73  ω   -137.00 -49.00   0.50    0.10    --  -70.00 -72.00-131.00  176
 74  ω   -136.00 -49.00   0.50    0.10    --  -70.00 -73.00 -17.75  174
 75  ω   -137.00 -49.00   0.50    0.10    --  -70.00 -72.00 118.48  176
 76  ω   -136.00 -49.00   0.50    0.10    --  -70.00 -73.00  84.12  174
 77  ω   -139.00 -53.00   0.50    0.10    --  -70.00 -64.00  53.08  172
;
_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      -0.0107230000
_diffrn_orient_matrix_UB_12      -0.1304905000
_diffrn_orient_matrix_UB_13      -0.0256403000
_diffrn_orient_matrix_UB_21      0.0854941000
_diffrn_orient_matrix_UB_22      -0.0415860000
_diffrn_orient_matrix_UB_23      0.0586429000
_diffrn_orient_matrix_UB_31      -0.1127196000
_diffrn_orient_matrix_UB_32      -0.0193307000
_diffrn_orient_matrix_UB_33      0.0469483000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4859
_reflns_number_total             5049
_reflns_odcompleteness_completeness 99.96
_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 1.171.39.28c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28c (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 2016 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5049
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.042
_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)+(0.0352P)²+0.6082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0753
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N1A-H1A = N1B-H1B
 0.93 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1A(H1AA), C1B(H1BA)
3.b Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10A,H10B), C11A(H11A,H11B), C8B(H8BA,
 H8BB), C9B(H9BA,H9BB), C10B(H10C,H10D), C11B(H11C,H11D)
3.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B)
;
_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
F1A F 0.14876(16) 0.23688(13) 0.08818(8) 0.0513(4) Uani 1 1 d . . . . .
F2A F 0.60829(12) 0.30838(12) 0.26252(6) 0.0377(3) Uani 1 1 d . . . . .
F3A F 0.50576(12) 0.31096(13) 0.36516(7) 0.0406(3) Uani 1 1 d . . . . .
F4A F 0.65527(12) 0.44673(13) 0.34423(8) 0.0433(3) Uani 1 1 d . . . . .
N1A N 0.37940(16) 0.52671(15) 0.33802(9) 0.0258(3) Uani 1 1 d D . . . .
H1A H 0.357(2) 0.4635(19) 0.3663(11) 0.031 Uiso 1 1 d DR . . . .
B1A B 0.5586(2) 0.3824(2) 0.31292(12) 0.0286(5) Uani 1 1 d . . . . .
C1A C 0.45455(19) 0.47157(19) 0.28003(10) 0.0263(4) Uani 1 1 d . . . . .
H1AA H 0.4971 0.5366 0.2557 0.032 Uiso 1 1 calc R . . . .
C2A C 0.37065(19) 0.40917(18) 0.22937(10) 0.0266(4) Uani 1 1 d . . . . .
C3A C 0.3606(2) 0.4518(2) 0.16207(11) 0.0326(5) Uani 1 1 d . . . . .
H3A H 0.4038 0.5203 0.1492 0.039 Uiso 1 1 calc R . . . .
C4A C 0.2870(2) 0.3938(2) 0.11407(11) 0.0384(5) Uani 1 1 d . . . . .
H4A H 0.2811 0.4221 0.0691 0.046 Uiso 1 1 calc R . . . .
C5A C 0.2236(2) 0.2943(2) 0.13447(11) 0.0354(5) Uani 1 1 d . . . . .
C6A C 0.2291(2) 0.2491(2) 0.20027(11) 0.0338(5) Uani 1 1 d . . . . .
H6A H 0.1837 0.1817 0.2127 0.041 Uiso 1 1 calc R . . . .
C7A C 0.3042(2) 0.30683(19) 0.24770(10) 0.0296(4) Uani 1 1 d . . . . .
H7A H 0.3103 0.2769 0.2923 0.036 Uiso 1 1 calc R . . . .
C8A C 0.4499(2) 0.6180(2) 0.38073(11) 0.0313(4) Uani 1 1 d . . . . .
H8AA H 0.5077 0.6619 0.3522 0.038 Uiso 1 1 calc R . . . .
H8AB H 0.4950 0.5785 0.4174 0.038 Uiso 1 1 calc R . . . .
C9A C 0.3526(2) 0.7027(2) 0.41046(13) 0.0404(5) Uani 1 1 d . . . . .
H9AA H 0.3661 0.7842 0.3945 0.048 Uiso 1 1 calc R . . . .
H9AB H 0.3552 0.7020 0.4604 0.048 Uiso 1 1 calc R . . . .
C10A C 0.2288(2) 0.6550(2) 0.38444(13) 0.0387(5) Uani 1 1 d . . . . .
H10A H 0.1921 0.6003 0.4175 0.046 Uiso 1 1 calc R . . . .
H10B H 0.1717 0.7201 0.3755 0.046 Uiso 1 1 calc R . . . .
C11A C 0.26261(19) 0.59043(18) 0.31873(11) 0.0306(4) Uani 1 1 d . . . . .
H11A H 0.1990 0.5339 0.3053 0.037 Uiso 1 1 calc R . . . .
H11B H 0.2763 0.6467 0.2814 0.037 Uiso 1 1 calc R . . . .
F1B F 0.54777(13) 0.61710(12) 0.67821(7) 0.0400(3) Uani 1 1 d . . . . .
F2B F 0.64814(11) 0.15096(10) 0.48030(6) 0.0303(3) Uani 1 1 d . . . . .
F3B F 0.83294(11) 0.06797(10) 0.51198(6) 0.0282(3) Uani 1 1 d . . . . .
F4B F 0.71045(11) 0.15090(10) 0.59317(6) 0.0277(3) Uani 1 1 d . . . . .
N1B N 0.82562(15) 0.32691(14) 0.43815(8) 0.0228(3) Uani 1 1 d D . . . .
H1B H 0.7469(18) 0.338(2) 0.4213(11) 0.027 Uiso 1 1 d DR . . . .
B1B B 0.7497(2) 0.16301(19) 0.52425(11) 0.0230(4) Uani 1 1 d . . . . .
C1B C 0.81600(18) 0.29464(17) 0.51373(10) 0.0232(4) Uani 1 1 d . . . . .
H1BA H 0.8997 0.2893 0.5323 0.028 Uiso 1 1 calc R . . . .
C2B C 0.74880(18) 0.39124(17) 0.55295(10) 0.0226(4) Uani 1 1 d . . . . .
C3B C 0.7937(2) 0.42706(18) 0.61721(11) 0.0289(4) Uani 1 1 d . . . . .
H3B H 0.8700 0.3991 0.6319 0.035 Uiso 1 1 calc R . . . .
C4B C 0.7274(2) 0.50301(19) 0.65945(11) 0.0331(5) Uani 1 1 d . . . . .
H4B H 0.7576 0.5256 0.7024 0.040 Uiso 1 1 calc R . . . .
C5B C 0.6158(2) 0.54422(18) 0.63639(10) 0.0292(4) Uani 1 1 d . . . . .
C6B C 0.5690(2) 0.51535(18) 0.57274(10) 0.0269(4) Uani 1 1 d . . . . .
H6B H 0.4946 0.5475 0.5578 0.032 Uiso 1 1 calc R . . . .
C7B C 0.63543(18) 0.43715(17) 0.53136(10) 0.0241(4) Uani 1 1 d . . . . .
H7B H 0.6041 0.4149 0.4886 0.029 Uiso 1 1 calc R . . . .
C8B C 0.8943(2) 0.4422(2) 0.42388(11) 0.0309(5) Uani 1 1 d . . . . .
H8BA H 0.9639 0.4507 0.4548 0.037 Uiso 1 1 calc R . . . .
H8BB H 0.8406 0.5111 0.4295 0.037 Uiso 1 1 calc R . . . .
C9B C 0.9378(2) 0.4314(2) 0.34927(11) 0.0362(5) Uani 1 1 d . . . . .
H9BA H 0.8890 0.4827 0.3195 0.043 Uiso 1 1 calc R . . . .
H9BB H 1.0236 0.4547 0.3453 0.043 Uiso 1 1 calc R . . . .
C10B C 0.9214(2) 0.3002(2) 0.32930(12) 0.0391(5) Uani 1 1 d . . . . .
H10C H 0.8544 0.2911 0.2967 0.047 Uiso 1 1 calc R . . . .
H10D H 0.9962 0.2687 0.3088 0.047 Uiso 1 1 calc R . . . .
C11B C 0.8927(2) 0.2361(2) 0.39568(11) 0.0345(5) Uani 1 1 d . . . . .
H11C H 0.8416 0.1663 0.3873 0.041 Uiso 1 1 calc R . . . .
H11D H 0.9678 0.2107 0.4185 0.041 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
F1A C5A 1.370(2) . ?
F2A B1A 1.389(3) . ?
F3A B1A 1.411(3) . ?
F4A B1A 1.408(3) . ?
N1A H1A 0.926(19) . ?
N1A C1A 1.520(3) . ?
N1A C8A 1.519(3) . ?
N1A C11A 1.501(2) . ?
B1A C1A 1.634(3) . ?
C1A H1AA 0.9800 . ?
C1A C2A 1.510(3) . ?
C2A C3A 1.394(3) . ?
C2A C7A 1.395(3) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.387(3) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.364(3) . ?
C5A C6A 1.374(3) . ?
C6A H6A 0.9300 . ?
C6A C7A 1.388(3) . ?
C7A H7A 0.9300 . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C9A 1.529(3) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.532(4) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C10A C11A 1.509(3) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
F1B C5B 1.365(2) . ?
F2B B1B 1.401(2) . ?
F3B B1B 1.412(2) . ?
F4B B1B 1.410(2) . ?
N1B H1B 0.923(19) . ?
N1B C1B 1.514(2) . ?
N1B C8B 1.511(3) . ?
N1B C11B 1.494(3) . ?
B1B C1B 1.646(3) . ?
C1B H1BA 0.9800 . ?
C1B C2B 1.506(3) . ?
C2B C3B 1.397(3) . ?
C2B C7B 1.397(3) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.381(3) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.371(3) . ?
C5B C6B 1.374(3) . ?
C6B H6B 0.9300 . ?
C6B C7B 1.387(3) . ?
C7B H7B 0.9300 . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C8B C9B 1.528(3) . ?
C9B H9BA 0.9700 . ?
C9B H9BB 0.9700 . ?
C9B C10B 1.522(4) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C10B C11B 1.505(3) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?

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
C1A N1A H1A 105.9(15) . . ?
C8A N1A H1A 108.7(15) . . ?
C8A N1A C1A 113.84(16) . . ?
C11A N1A H1A 106.4(15) . . ?
C11A N1A C1A 117.40(16) . . ?
C11A N1A C8A 104.21(16) . . ?
F2A B1A F3A 109.21(19) . . ?
F2A B1A F4A 108.46(18) . . ?
F2A B1A C1A 110.75(17) . . ?
F3A B1A C1A 109.99(17) . . ?
F4A B1A F3A 106.26(17) . . ?
F4A B1A C1A 112.04(18) . . ?
N1A C1A B1A 109.12(16) . . ?
N1A C1A H1AA 108.1 . . ?
B1A C1A H1AA 108.1 . . ?
C2A C1A N1A 110.13(16) . . ?
C2A C1A B1A 113.09(17) . . ?
C2A C1A H1AA 108.1 . . ?
C3A C2A C1A 120.04(19) . . ?
C3A C2A C7A 118.48(19) . . ?
C7A C2A C1A 121.47(18) . . ?
C2A C3A H3A 119.5 . . ?
C4A C3A C2A 121.1(2) . . ?
C4A C3A H3A 119.5 . . ?
C3A C4A H4A 120.8 . . ?
C5A C4A C3A 118.3(2) . . ?
C5A C4A H4A 120.8 . . ?
F1A C5A C6A 117.7(2) . . ?
C4A C5A F1A 119.2(2) . . ?
C4A C5A C6A 123.1(2) . . ?
C5A C6A H6A 120.9 . . ?
C5A C6A C7A 118.2(2) . . ?
C7A C6A H6A 120.9 . . ?
C2A C7A H7A 119.6 . . ?
C6A C7A C2A 120.87(19) . . ?
C6A C7A H7A 119.6 . . ?
N1A C8A H8AA 110.6 . . ?
N1A C8A H8AB 110.6 . . ?
N1A C8A C9A 105.70(18) . . ?
H8AA C8A H8AB 108.7 . . ?
C9A C8A H8AA 110.6 . . ?
C9A C8A H8AB 110.6 . . ?
C8A C9A H9AA 110.6 . . ?
C8A C9A H9AB 110.6 . . ?
C8A C9A C10A 105.56(18) . . ?
H9AA C9A H9AB 108.8 . . ?
C10A C9A H9AA 110.6 . . ?
C10A C9A H9AB 110.6 . . ?
C9A C10A H10A 111.1 . . ?
C9A C10A H10B 111.1 . . ?
H10A C10A H10B 109.1 . . ?
C11A C10A C9A 103.29(19) . . ?
C11A C10A H10A 111.1 . . ?
C11A C10A H10B 111.1 . . ?
N1A C11A C10A 102.72(17) . . ?
N1A C11A H11A 111.2 . . ?
N1A C11A H11B 111.2 . . ?
C10A C11A H11A 111.2 . . ?
C10A C11A H11B 111.2 . . ?
H11A C11A H11B 109.1 . . ?
C1B N1B H1B 108.1(14) . . ?
C8B N1B H1B 106.4(15) . . ?
C8B N1B C1B 114.42(15) . . ?
C11B N1B H1B 110.1(15) . . ?
C11B N1B C1B 114.05(15) . . ?
C11B N1B C8B 103.47(16) . . ?
F2B B1B F3B 109.24(16) . . ?
F2B B1B F4B 109.30(16) . . ?
F2B B1B C1B 110.74(15) . . ?
F3B B1B C1B 111.51(16) . . ?
F4B B1B F3B 106.37(15) . . ?
F4B B1B C1B 109.58(16) . . ?
N1B C1B B1B 111.21(15) . . ?
N1B C1B H1BA 107.9 . . ?
B1B C1B H1BA 107.9 . . ?
C2B C1B N1B 110.70(15) . . ?
C2B C1B B1B 111.19(15) . . ?
C2B C1B H1BA 107.9 . . ?
C3B C2B C1B 119.06(18) . . ?
C3B C2B C7B 118.08(19) . . ?
C7B C2B C1B 122.45(17) . . ?
C2B C3B H3B 119.2 . . ?
C4B C3B C2B 121.51(19) . . ?
C4B C3B H3B 119.2 . . ?
C3B C4B H4B 120.9 . . ?
C5B C4B C3B 118.19(19) . . ?
C5B C4B H4B 120.9 . . ?
F1B C5B C4B 118.90(19) . . ?
F1B C5B C6B 118.3(2) . . ?
C4B C5B C6B 122.8(2) . . ?
C5B C6B H6B 120.8 . . ?
C5B C6B C7B 118.4(2) . . ?
C7B C6B H6B 120.8 . . ?
C2B C7B H7B 119.5 . . ?
C6B C7B C2B 120.95(18) . . ?
C6B C7B H7B 119.5 . . ?
N1B C8B H8BA 110.7 . . ?
N1B C8B H8BB 110.7 . . ?
N1B C8B C9B 105.02(18) . . ?
H8BA C8B H8BB 108.8 . . ?
C9B C8B H8BA 110.7 . . ?
C9B C8B H8BB 110.7 . . ?
C8B C9B H9BA 110.5 . . ?
C8B C9B H9BB 110.5 . . ?
H9BA C9B H9BB 108.7 . . ?
C10B C9B C8B 106.32(17) . . ?
C10B C9B H9BA 110.5 . . ?
C10B C9B H9BB 110.5 . . ?
C9B C10B H10C 110.7 . . ?
C9B C10B H10D 110.7 . . ?
H10C C10B H10D 108.8 . . ?
C11B C10B C9B 105.14(19) . . ?
C11B C10B H10C 110.7 . . ?
C11B C10B H10D 110.7 . . ?
N1B C11B C10B 104.62(17) . . ?
N1B C11B H11C 110.8 . . ?
N1B C11B H11D 110.8 . . ?
C10B C11B H11C 110.8 . . ?
C10B C11B H11D 110.8 . . ?
H11C C11B H11D 108.9 . . ?

_olex2_submission_original_sample_id jb120817_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.310
_oxdiff_exptl_absorpt_empirical_full_min 0.837
