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

####################################################################### 
# 
# 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. 
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data_a
_database_code_depnum_ccdc_archive 'CCDC 1545030'
#Added by publCIF



_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  No
# publcif _publ_body_element loop end
_audit_creation_date             2017-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
1-phenyl-3-(trifluoromethyl)-3H,4aH-[1,3]oxazino[3,2-a]quinolin-3-ol
_chemical_formula_moiety         'C19 H14 F3 N O2'
_chemical_formula_sum            'C19 H14 F3 N O2'
_chemical_formula_weight         345.31
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.9333(7)
_cell_length_b                   9.8491(3)
_cell_length_c                   16.6571(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.9990(10)
_cell_angle_gamma                90
_cell_volume                     3229.95(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    321
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.6
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0652 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.9116.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'pale light yellow'
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21803
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.138
_diffrn_reflns_theta_min         2.476
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   IuS
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2852
_reflns_number_total             3197
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.032
_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)+(0.0459P)²+3.1673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.42767(4) 0.20103(8) 0.98487(5) 0.02081(19) Uani 1 1 d . . . . .
F2 F 0.36365(4) 0.29688(8) 1.06152(4) 0.0218(2) Uani 1 1 d . . . . .
F3 F 0.41346(4) 0.41801(8) 0.98022(5) 0.0250(2) Uani 1 1 d . . . . .
O1 O 0.29214(4) 0.15506(9) 0.93816(5) 0.0153(2) Uani 1 1 d . . . . .
O2 O 0.27461(5) 0.38901(9) 0.92383(6) 0.0177(2) Uani 1 1 d . . . . .
H2 H 0.2569(9) 0.3763(17) 0.9669(11) 0.027 Uiso 1 1 d R . . . .
N1 N 0.32495(5) 0.05051(10) 0.82249(6) 0.0149(2) Uani 1 1 d . . . . .
C1 C 0.43329(8) -0.31564(15) 0.86062(9) 0.0280(3) Uani 1 1 d . . . . .
H1 H 0.4564 -0.4003 0.8656 0.034 Uiso 1 1 calc R . . . .
C2 C 0.36645(8) -0.30737(14) 0.87376(8) 0.0254(3) Uani 1 1 d . . . . .
H2A H 0.3443 -0.3864 0.8892 0.031 Uiso 1 1 calc R . . . .
C3 C 0.33136(7) -0.18438(13) 0.86453(8) 0.0199(3) Uani 1 1 d . . . . .
C4 C 0.36377(6) -0.06881(13) 0.83867(7) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.35177(6) 0.17252(12) 0.79586(7) 0.0142(3) Uani 1 1 d . . . . .
C6 C 0.37875(6) 0.17031(13) 0.71783(7) 0.0145(3) Uani 1 1 d . . . . .
C7 C 0.35939(6) 0.06746(13) 0.66100(8) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.3307 -0.0039 0.6735 0.021 Uiso 1 1 calc R . . . .
C8 C 0.38202(7) 0.06951(14) 0.58627(8) 0.0200(3) Uani 1 1 d . . . . .
H8 H 0.3684 -0.0003 0.5478 0.024 Uiso 1 1 calc R . . . .
C9 C 0.42427(7) 0.17235(15) 0.56731(8) 0.0216(3) Uani 1 1 d . . . . .
H9 H 0.4399 0.1727 0.5163 0.026 Uiso 1 1 calc R . . . .
C10 C 0.26804(6) 0.07666(13) 0.86372(7) 0.0162(3) Uani 1 1 d . . . . .
H10 H 0.2339 0.1323 0.8274 0.019 Uiso 1 1 calc R . . . .
C11 C 0.31994(6) 0.28212(12) 0.91969(7) 0.0144(3) Uani 1 1 d . . . . .
C12 C 0.34298(6) 0.28553(13) 0.83776(7) 0.0151(3) Uani 1 1 d . . . . .
H12 H 0.3516 0.3710 0.8150 0.018 Uiso 1 1 calc R . . . .
C13 C 0.44359(7) 0.27489(15) 0.62335(8) 0.0217(3) Uani 1 1 d . . . . .
H13 H 0.4723 0.3459 0.6104 0.026 Uiso 1 1 calc R . . . .
C14 C 0.42111(6) 0.27409(13) 0.69821(8) 0.0178(3) Uani 1 1 d . . . . .
H14 H 0.4346 0.3445 0.7363 0.021 Uiso 1 1 calc R . . . .
C15 C 0.38189(6) 0.29919(13) 0.98712(8) 0.0163(3) Uani 1 1 d . . . . .
C16 C 0.23433(7) -0.04861(14) 0.88754(8) 0.0212(3) Uani 1 1 d . . . . .
H16 H 0.1910 -0.0421 0.9042 0.025 Uiso 1 1 calc R . . . .
C17 C 0.26379(7) -0.16948(14) 0.88593(8) 0.0223(3) Uani 1 1 d . . . . .
H17 H 0.2401 -0.2481 0.8991 0.027 Uiso 1 1 calc R . . . .
C18 C 0.43223(7) -0.07593(14) 0.82935(7) 0.0182(3) Uani 1 1 d . . . . .
H18 H 0.4553 0.0031 0.8157 0.022 Uiso 1 1 calc R . . . .
C19 C 0.46631(7) -0.19944(14) 0.84018(8) 0.0236(3) Uani 1 1 d . . . . .
H19 H 0.5127 -0.2044 0.8335 0.028 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
F1 C15 1.3341(14) . ?
F2 C15 1.3452(14) . ?
F3 C15 1.3422(14) . ?
O1 C10 1.4758(15) . ?
O1 C11 1.4217(15) . ?
O2 H2 0.856(18) . ?
O2 C11 1.3961(15) . ?
N1 C4 1.4097(16) . ?
N1 C5 1.4146(16) . ?
N1 C10 1.4383(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(2) . ?
C1 C19 1.389(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3952(19) . ?
C3 C4 1.4091(18) . ?
C3 C17 1.4537(19) . ?
C4 C18 1.3992(18) . ?
C5 C6 1.4824(16) . ?
C5 C12 1.3398(18) . ?
C6 C7 1.3989(18) . ?
C6 C14 1.3967(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3889(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(2) . ?
C9 H9 0.9500 . ?
C9 C13 1.388(2) . ?
C10 H10 1.0000 . ?
C10 C16 1.4881(17) . ?
C11 C12 1.5068(16) . ?
C11 C15 1.5429(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.3895(18) . ?
C14 H14 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.330(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.3912(19) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C10 111.43(9) . . ?
C11 O2 H2 106.6(11) . . ?
C4 N1 C5 123.03(10) . . ?
C4 N1 C10 120.56(10) . . ?
C5 N1 C10 111.27(10) . . ?
C2 C1 H1 120.2 . . ?
C2 C1 C19 119.64(13) . . ?
C19 C1 H1 120.2 . . ?
C1 C2 H2A 119.6 . . ?
C1 C2 C3 120.75(13) . . ?
C3 C2 H2A 119.6 . . ?
C2 C3 C4 119.29(13) . . ?
C2 C3 C17 121.89(12) . . ?
C4 C3 C17 118.69(12) . . ?
C3 C4 N1 117.88(11) . . ?
C18 C4 N1 122.43(11) . . ?
C18 C4 C3 119.68(12) . . ?
N1 C5 C6 117.99(11) . . ?
C12 C5 N1 117.11(11) . . ?
C12 C5 C6 124.33(11) . . ?
C7 C6 C5 120.29(11) . . ?
C14 C6 C5 120.65(11) . . ?
C14 C6 C7 118.98(11) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.14(12) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.61(12) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C13 119.57(12) . . ?
C13 C9 H9 120.2 . . ?
O1 C10 H10 108.8 . . ?
O1 C10 C16 108.12(10) . . ?
N1 C10 O1 108.50(9) . . ?
N1 C10 H10 108.8 . . ?
N1 C10 C16 113.67(11) . . ?
C16 C10 H10 108.8 . . ?
O1 C11 C12 113.57(10) . . ?
O1 C11 C15 103.48(9) . . ?
O2 C11 O1 112.08(9) . . ?
O2 C11 C12 108.62(10) . . ?
O2 C11 C15 109.41(10) . . ?
C12 C11 C15 109.53(10) . . ?
C5 C12 C11 122.45(11) . . ?
C5 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C9 C13 H13 119.8 . . ?
C9 C13 C14 120.32(12) . . ?
C14 C13 H13 119.8 . . ?
C6 C14 H14 119.8 . . ?
C13 C14 C6 120.38(12) . . ?
C13 C14 H14 119.8 . . ?
F1 C15 F2 107.35(10) . . ?
F1 C15 F3 107.30(10) . . ?
F1 C15 C11 111.94(10) . . ?
F2 C15 C11 111.60(10) . . ?
F3 C15 F2 106.95(10) . . ?
F3 C15 C11 111.43(10) . . ?
C10 C16 H16 119.4 . . ?
C17 C16 C10 121.19(12) . . ?
C17 C16 H16 119.4 . . ?
C3 C17 H17 119.2 . . ?
C16 C17 C3 121.63(12) . . ?
C16 C17 H17 119.2 . . ?
C4 C18 H18 120.2 . . ?
C19 C18 C4 119.63(12) . . ?
C19 C18 H18 120.2 . . ?
C1 C19 C18 120.78(13) . . ?
C1 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C16 C17 -106.99(14) . . . . ?
O1 C11 C12 C5 -15.32(16) . . . . ?
O1 C11 C15 F1 61.72(12) . . . . ?
O1 C11 C15 F2 -58.63(12) . . . . ?
O1 C11 C15 F3 -178.12(9) . . . . ?
O2 C11 C12 C5 -140.75(12) . . . . ?
O2 C11 C15 F1 -178.66(9) . . . . ?
O2 C11 C15 F2 60.99(13) . . . . ?
O2 C11 C15 F3 -58.49(13) . . . . ?
N1 C4 C18 C19 -175.01(11) . . . . ?
N1 C5 C6 C7 19.79(16) . . . . ?
N1 C5 C6 C14 -163.35(11) . . . . ?
N1 C5 C12 C11 13.24(17) . . . . ?
N1 C10 C16 C17 13.54(18) . . . . ?
C1 C2 C3 C4 2.3(2) . . . . ?
C1 C2 C3 C17 -173.53(13) . . . . ?
C2 C1 C19 C18 -2.7(2) . . . . ?
C2 C3 C4 N1 174.08(11) . . . . ?
C2 C3 C4 C18 -5.43(18) . . . . ?
C2 C3 C17 C16 170.74(13) . . . . ?
C3 C4 C18 C19 4.48(18) . . . . ?
C4 N1 C5 C6 60.56(15) . . . . ?
C4 N1 C5 C12 -127.78(12) . . . . ?
C4 N1 C10 O1 91.21(13) . . . . ?
C4 N1 C10 C16 -29.10(16) . . . . ?
C4 C3 C17 C16 -5.14(19) . . . . ?
C4 C18 C19 C1 -0.39(19) . . . . ?
C5 N1 C4 C3 -179.69(11) . . . . ?
C5 N1 C4 C18 -0.19(18) . . . . ?
C5 N1 C10 O1 -64.14(12) . . . . ?
C5 N1 C10 C16 175.54(10) . . . . ?
C5 C6 C7 C8 176.73(11) . . . . ?
C5 C6 C14 C13 -176.90(11) . . . . ?
C6 C5 C12 C11 -175.68(11) . . . . ?
C6 C7 C8 C9 0.49(19) . . . . ?
C7 C6 C14 C13 0.00(18) . . . . ?
C7 C8 C9 C13 -0.6(2) . . . . ?
C8 C9 C13 C14 0.4(2) . . . . ?
C9 C13 C14 C6 -0.1(2) . . . . ?
C10 O1 C11 O2 101.39(11) . . . . ?
C10 O1 C11 C12 -22.17(13) . . . . ?
C10 O1 C11 C15 -140.83(9) . . . . ?
C10 N1 C4 C3 27.92(16) . . . . ?
C10 N1 C4 C18 -152.58(12) . . . . ?
C10 N1 C5 C6 -144.80(11) . . . . ?
C10 N1 C5 C12 26.86(15) . . . . ?
C10 C16 C17 C3 2.9(2) . . . . ?
C11 O1 C10 N1 61.23(12) . . . . ?
C11 O1 C10 C16 -175.06(10) . . . . ?
C12 C5 C6 C7 -151.22(13) . . . . ?
C12 C5 C6 C14 25.64(18) . . . . ?
C12 C11 C15 F1 -59.71(13) . . . . ?
C12 C11 C15 F2 179.94(10) . . . . ?
C12 C11 C15 F3 60.46(13) . . . . ?
C14 C6 C7 C8 -0.19(18) . . . . ?
C15 C11 C12 C5 99.81(14) . . . . ?
C17 C3 C4 N1 -9.93(17) . . . . ?
C17 C3 C4 C18 170.56(12) . . . . ?
C19 C1 C2 C3 1.8(2) . . . . ?

_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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1545031'
#Added by publCIF



_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  No
# publcif _publ_body_element loop end
_audit_creation_date             2017-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 Br N, C19 H13 Br F3 N O2'
_chemical_formula_sum            'C28 H19 Br2 F3 N2 O2'
_chemical_formula_weight         632.27
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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                   10.054(5)
_cell_length_b                   15.229(9)
_cell_length_c                   17.101(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.46(2)
_cell_angle_gamma                90
_cell_volume                     2607(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    632
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      2.26
_cell_measurement_theta_min      23.5
_shelx_estimated_absorpt_T_max   0.533
_shelx_estimated_absorpt_T_min   0.294
_exptl_absorpt_coefficient_mu    3.160
_exptl_absorpt_correction_T_max  0.5330
_exptl_absorpt_correction_T_min  0.2940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.513
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.228
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            52763
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.734
_diffrn_reflns_theta_min         2.260
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   IuS
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3696
_reflns_number_total             5518
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00181(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.021
_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)+(0.0258P)²+2.6633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C24(H24), C25(H25), C26(H26), C28(H28)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Br1 Br 0.13319(5) 0.60852(2) 0.89383(3) 0.08246(17) Uani 1 1 d . . . . .
Br2 Br 0.58695(5) 0.47529(3) 0.90797(2) 0.07271(16) Uani 1 1 d . . . . .
O1 O 0.50198(19) 0.44113(12) 0.71663(11) 0.0383(5) Uani 1 1 d . . . . .
F2 F 0.3059(2) 0.35264(16) 0.55335(12) 0.0765(6) Uani 1 1 d . . . . .
F3 F 0.4158(2) 0.47445(14) 0.56303(12) 0.0738(6) Uani 1 1 d . . . . .
F4 F 0.2566(2) 0.45176(15) 0.63559(13) 0.0762(6) Uani 1 1 d . . . . .
O0AA O 0.3923(2) 0.30604(14) 0.70607(14) 0.0500(6) Uani 1 1 d . . . . .
H0AA H 0.342(4) 0.326(3) 0.735(2) 0.075 Uiso 1 1 d R . . . .
N1 N 0.2196(3) 0.36692(17) 0.80858(15) 0.0507(7) Uani 1 1 d . . . . .
N2 N 0.7295(2) 0.42168(14) 0.69430(13) 0.0341(5) Uani 1 1 d . . . . .
C1 C 0.2165(3) 0.4506(2) 0.82690(19) 0.0525(8) Uani 1 1 d . . . . .
H1 H 0.2808 0.4875 0.8091 0.063 Uiso 1 1 calc R . . . .
C2 C 0.1215(3) 0.4868(2) 0.87175(19) 0.0487(8) Uani 1 1 d . . . . .
C3 C 0.0236(3) 0.4360(2) 0.89661(19) 0.0524(8) Uani 1 1 d . . . . .
H3 H -0.0409 0.4601 0.9257 0.063 Uiso 1 1 calc R . . . .
C4 C 0.0210(3) 0.3450(2) 0.87754(17) 0.0456(8) Uani 1 1 d . . . . .
C5 C -0.0762(4) 0.2856(3) 0.9002(2) 0.0660(10) Uani 1 1 d . . . . .
H5 H -0.1445 0.3059 0.9285 0.079 Uiso 1 1 calc R . . . .
C6 C -0.0707(4) 0.1995(3) 0.8811(2) 0.0746(12) Uani 1 1 d . . . . .
H6 H -0.1357 0.1611 0.8961 0.090 Uiso 1 1 calc R . . . .
C7 C 0.1237(3) 0.31296(19) 0.83450(16) 0.0424(7) Uani 1 1 d . . . . .
C8 C 0.0319(5) 0.1680(2) 0.8391(2) 0.0699(11) Uani 1 1 d . . . . .
H8 H 0.0347 0.1087 0.8266 0.084 Uiso 1 1 calc R . . . .
C9 C 0.1279(4) 0.2227(2) 0.81630(19) 0.0567(9) Uani 1 1 d . . . . .
H9 H 0.1960 0.2007 0.7888 0.068 Uiso 1 1 calc R . . . .
C10 C 0.9474(4) 0.6479(3) 0.6476(2) 0.0723(11) Uani 1 1 d . . . . .
H10 H 0.9994 0.6967 0.6386 0.087 Uiso 1 1 calc R . . . .
C11 C 0.9238(4) 0.5850(2) 0.5902(2) 0.0640(10) Uani 1 1 d . . . . .
H11 H 0.9591 0.5921 0.5423 0.077 Uiso 1 1 calc R . . . .
C12 C 0.8480(3) 0.5110(2) 0.60301(18) 0.0459(8) Uani 1 1 d . . . . .
H12 H 0.8310 0.4695 0.5634 0.055 Uiso 1 1 calc R . . . .
C13 C 0.7974(3) 0.49896(18) 0.67539(16) 0.0370(7) Uani 1 1 d . . . . .
C14 C 0.6962(3) 0.35402(17) 0.63829(15) 0.0337(6) Uani 1 1 d . . . . .
C15 C 0.8056(3) 0.30822(17) 0.60288(15) 0.0348(6) Uani 1 1 d . . . . .
C16 C 0.7839(3) 0.2675(2) 0.53007(17) 0.0445(7) Uani 1 1 d . . . . .
H16 H 0.7006 0.2717 0.5015 0.053 Uiso 1 1 calc R . . . .
C17 C 0.8849(3) 0.2210(2) 0.49978(19) 0.0534(9) Uani 1 1 d . . . . .
H17 H 0.8689 0.1935 0.4513 0.064 Uiso 1 1 calc R . . . .
C18 C 1.0081(3) 0.2151(2) 0.5403(2) 0.0544(9) Uani 1 1 d . . . . .
H18 H 1.0756 0.1834 0.5196 0.065 Uiso 1 1 calc R . . . .
C19 C 0.8943(4) 0.6385(2) 0.7177(2) 0.0644(10) Uani 1 1 d . . . . .
H19 H 0.9095 0.6815 0.7560 0.077 Uiso 1 1 calc R . . . .
C20 C 0.8173(3) 0.5648(2) 0.73254(18) 0.0460(8) Uani 1 1 d . . . . .
C21 C 0.6360(3) 0.42325(18) 0.75296(15) 0.0355(7) Uani 1 1 d . . . . .
H21 H 0.6361 0.3655 0.7782 0.043 Uiso 1 1 calc R . . . .
C22 C 0.4568(3) 0.37066(18) 0.66673(17) 0.0391(7) Uani 1 1 d . . . . .
C23 C 0.3583(3) 0.4135(2) 0.6040(2) 0.0539(9) Uani 1 1 d . . . . .
C24 C 0.5687(3) 0.32730(18) 0.62879(17) 0.0398(7) Uani 1 1 d . . . . .
H24 H 0.5482 0.2789 0.5967 0.048 Uiso 1 1 calc R . . . .
C25 C 0.9315(3) 0.3019(2) 0.64291(18) 0.0473(8) Uani 1 1 d . . . . .
H25 H 0.9485 0.3291 0.6916 0.057 Uiso 1 1 calc R . . . .
C26 C 1.0325(3) 0.2558(2) 0.6115(2) 0.0565(9) Uani 1 1 d . . . . .
H26 H 1.1169 0.2525 0.6388 0.068 Uiso 1 1 calc R . . . .
C27 C 0.6708(3) 0.49091(19) 0.81450(16) 0.0433(7) Uani 1 1 d . . . . .
C28 C 0.7548(3) 0.5560(2) 0.80508(18) 0.0505(8) Uani 1 1 d . . . . .
H28 H 0.7739 0.5964 0.8453 0.061 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
Br1 C2 1.893(3) . ?
Br2 C27 1.892(3) . ?
O1 C21 1.455(3) . ?
O1 C22 1.419(3) . ?
F2 C23 1.342(4) . ?
F3 C23 1.328(4) . ?
F4 C23 1.335(4) . ?
O0AA H0AA 0.80(4) . ?
O0AA C22 1.387(3) . ?
N1 C1 1.313(4) . ?
N1 C7 1.372(4) . ?
N2 C13 1.413(3) . ?
N2 C14 1.425(3) . ?
N2 C21 1.439(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.394(5) . ?
C2 C3 1.352(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.423(4) . ?
C4 C5 1.412(5) . ?
C4 C7 1.411(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.354(5) . ?
C6 H6 0.9300 . ?
C6 C8 1.398(6) . ?
C7 C9 1.411(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.360(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.375(5) . ?
C10 C19 1.366(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(4) . ?
C13 C20 1.402(4) . ?
C14 C15 1.480(4) . ?
C14 C24 1.339(4) . ?
C15 C16 1.389(4) . ?
C15 C25 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.364(5) . ?
C18 H18 0.9300 . ?
C18 C26 1.367(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.399(5) . ?
C20 C28 1.449(4) . ?
C21 H21 0.9800 . ?
C21 C27 1.490(4) . ?
C22 C23 1.535(4) . ?
C22 C24 1.504(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.385(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.322(4) . ?
C28 H28 0.9300 . ?

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
C22 O1 C21 110.2(2) . . ?
C22 O0AA H0AA 112(3) . . ?
C1 N1 C7 118.1(3) . . ?
C13 N2 C14 122.4(2) . . ?
C13 N2 C21 120.5(2) . . ?
C14 N2 C21 110.7(2) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.2(3) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 Br1 117.7(2) . . ?
C3 C2 Br1 122.1(3) . . ?
C3 C2 C1 120.3(3) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 123.9(3) . . ?
C7 C4 C3 117.2(3) . . ?
C7 C4 C5 118.8(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C8 120.3(4) . . ?
C8 C6 H6 119.8 . . ?
N1 C7 C4 122.2(3) . . ?
N1 C7 C9 118.4(3) . . ?
C9 C7 C4 119.4(3) . . ?
C6 C8 H8 119.5 . . ?
C9 C8 C6 121.1(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C9 H9 120.1 . . ?
C8 C9 C7 119.8(4) . . ?
C8 C9 H9 120.1 . . ?
C11 C10 H10 120.1 . . ?
C19 C10 H10 120.1 . . ?
C19 C10 C11 119.8(3) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.9(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 N2 122.5(3) . . ?
C12 C13 C20 119.0(3) . . ?
C20 C13 N2 118.5(3) . . ?
N2 C14 C15 118.6(2) . . ?
C24 C14 N2 117.6(2) . . ?
C24 C14 C15 123.2(3) . . ?
C16 C15 C14 121.2(3) . . ?
C25 C15 C14 120.7(2) . . ?
C25 C15 C16 118.1(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C26 120.0(3) . . ?
C26 C18 H18 120.0 . . ?
C10 C19 H19 119.6 . . ?
C10 C19 C20 120.9(3) . . ?
C20 C19 H19 119.6 . . ?
C13 C20 C28 119.0(3) . . ?
C19 C20 C13 119.4(3) . . ?
C19 C20 C28 121.5(3) . . ?
O1 C21 H21 108.6 . . ?
O1 C21 C27 108.5(2) . . ?
N2 C21 O1 110.2(2) . . ?
N2 C21 H21 108.6 . . ?
N2 C21 C27 112.2(2) . . ?
C27 C21 H21 108.6 . . ?
O1 C22 C23 104.3(2) . . ?
O1 C22 C24 112.4(2) . . ?
O0AA C22 O1 112.5(2) . . ?
O0AA C22 C23 109.9(3) . . ?
O0AA C22 C24 107.5(2) . . ?
C24 C22 C23 110.2(2) . . ?
F2 C23 C22 110.2(3) . . ?
F3 C23 F2 107.8(3) . . ?
F3 C23 F4 107.3(3) . . ?
F3 C23 C22 112.4(3) . . ?
F4 C23 F2 107.1(3) . . ?
F4 C23 C22 111.8(3) . . ?
C14 C24 C22 124.1(3) . . ?
C14 C24 H24 117.9 . . ?
C22 C24 H24 117.9 . . ?
C15 C25 H25 119.6 . . ?
C15 C25 C26 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C18 C26 C25 120.0(3) . . ?
C18 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C21 C27 Br2 114.6(2) . . ?
C28 C27 Br2 122.6(2) . . ?
C28 C27 C21 122.8(3) . . ?
C20 C28 H28 119.7 . . ?
C27 C28 C20 120.5(3) . . ?
C27 C28 H28 119.7 . . ?

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
Br1 C2 C3 C4 179.8(2) . . . . ?
Br2 C27 C28 C20 179.6(2) . . . . ?
O1 C21 C27 Br2 75.4(2) . . . . ?
O1 C21 C27 C28 -105.4(3) . . . . ?
O1 C22 C23 F2 -178.8(2) . . . . ?
O1 C22 C23 F3 60.9(3) . . . . ?
O1 C22 C23 F4 -59.9(3) . . . . ?
O1 C22 C24 C14 -2.5(4) . . . . ?
O0AA C22 C23 F2 -58.0(3) . . . . ?
O0AA C22 C23 F3 -178.3(3) . . . . ?
O0AA C22 C23 F4 60.9(3) . . . . ?
O0AA C22 C24 C14 -126.9(3) . . . . ?
N1 C1 C2 Br1 179.2(3) . . . . ?
N1 C1 C2 C3 -2.2(5) . . . . ?
N1 C7 C9 C8 -178.0(3) . . . . ?
N2 C13 C20 C19 174.4(3) . . . . ?
N2 C13 C20 C28 -7.0(4) . . . . ?
N2 C14 C15 C16 -155.6(3) . . . . ?
N2 C14 C15 C25 26.9(4) . . . . ?
N2 C14 C24 C22 7.0(4) . . . . ?
N2 C21 C27 Br2 -162.51(19) . . . . ?
N2 C21 C27 C28 16.6(4) . . . . ?
C1 N1 C7 C4 2.0(5) . . . . ?
C1 N1 C7 C9 -178.8(3) . . . . ?
C1 C2 C3 C4 1.2(5) . . . . ?
C2 C3 C4 C5 -180.0(3) . . . . ?
C2 C3 C4 C7 1.1(5) . . . . ?
C3 C4 C5 C6 -178.7(4) . . . . ?
C3 C4 C7 N1 -2.8(4) . . . . ?
C3 C4 C7 C9 178.0(3) . . . . ?
C4 C5 C6 C8 0.4(6) . . . . ?
C4 C7 C9 C8 1.2(5) . . . . ?
C5 C4 C7 N1 178.2(3) . . . . ?
C5 C4 C7 C9 -1.0(5) . . . . ?
C5 C6 C8 C9 -0.2(6) . . . . ?
C6 C8 C9 C7 -0.6(5) . . . . ?
C7 N1 C1 C2 0.5(5) . . . . ?
C7 C4 C5 C6 0.2(5) . . . . ?
C10 C11 C12 C13 -1.4(5) . . . . ?
C10 C19 C20 C13 1.6(5) . . . . ?
C10 C19 C20 C28 -176.9(4) . . . . ?
C11 C10 C19 C20 0.9(6) . . . . ?
C11 C12 C13 N2 -174.4(3) . . . . ?
C11 C12 C13 C20 3.9(5) . . . . ?
C12 C13 C20 C19 -3.9(5) . . . . ?
C12 C13 C20 C28 174.6(3) . . . . ?
C13 N2 C14 C15 61.6(3) . . . . ?
C13 N2 C14 C24 -127.4(3) . . . . ?
C13 N2 C21 O1 91.3(3) . . . . ?
C13 N2 C21 C27 -29.8(3) . . . . ?
C13 C20 C28 C27 -5.9(5) . . . . ?
C14 N2 C13 C12 -6.4(4) . . . . ?
C14 N2 C13 C20 175.3(3) . . . . ?
C14 N2 C21 O1 -61.2(3) . . . . ?
C14 N2 C21 C27 177.7(2) . . . . ?
C14 C15 C16 C17 -176.4(3) . . . . ?
C14 C15 C25 C26 177.1(3) . . . . ?
C15 C14 C24 C22 177.5(3) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C15 C25 C26 C18 -0.6(5) . . . . ?
C16 C15 C25 C26 -0.5(5) . . . . ?
C16 C17 C18 C26 -0.3(5) . . . . ?
C17 C18 C26 C25 1.0(5) . . . . ?
C19 C10 C11 C12 -1.0(6) . . . . ?
C19 C20 C28 C27 172.6(3) . . . . ?
C21 O1 C22 O0AA 89.0(3) . . . . ?
C21 O1 C22 C23 -152.0(2) . . . . ?
C21 O1 C22 C24 -32.6(3) . . . . ?
C21 N2 C13 C12 -155.6(3) . . . . ?
C21 N2 C13 C20 26.1(4) . . . . ?
C21 N2 C14 C15 -146.5(2) . . . . ?
C21 N2 C14 C24 24.5(3) . . . . ?
C21 C27 C28 C20 0.5(5) . . . . ?
C22 O1 C21 N2 66.0(3) . . . . ?
C22 O1 C21 C27 -170.7(2) . . . . ?
C23 C22 C24 C14 113.4(3) . . . . ?
C24 C14 C15 C16 34.0(4) . . . . ?
C24 C14 C15 C25 -143.6(3) . . . . ?
C24 C22 C23 F2 60.3(3) . . . . ?
C24 C22 C23 F3 -60.0(3) . . . . ?
C24 C22 C23 F4 179.2(3) . . . . ?
C25 C15 C16 C17 1.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

