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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tx32
_database_code_depnum_ccdc_archive 'CCDC 1874173'
loop_
_audit_author_name
_audit_author_address
ioo
;efsdfreferwg
China
;
_audit_update_record             
;
2018-10-19 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2018-10-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 Br N O2'
_chemical_formula_sum            'C18 H14 Br N O2'
_chemical_formula_weight         356.21
_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 0.0181 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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.86050(10)
_cell_length_b                   21.1565(4)
_cell_length_c                   7.84150(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.0250(10)
_cell_angle_gamma                90
_cell_volume                     1467.90(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10799
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      74.900
_cell_measurement_theta_min      4.1290
_shelx_estimated_absorpt_T_max   0.528
_shelx_estimated_absorpt_T_min   0.370
_exptl_absorpt_coefficient_mu    3.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.189
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13497
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.388
_diffrn_reflns_theta_min         4.179
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2707
_reflns_number_total             2934
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.059
_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)+(0.0715P)²+0.7326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1054
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.64885(3) 0.74061(2) 0.53032(3) 0.03212(14) Uani 1 1 d . . . . .
O1 O 0.13475(19) 0.41675(8) 0.3562(2) 0.0278(4) Uani 1 1 d . . . . .
O2 O 0.15613(17) 0.48216(8) 0.66807(18) 0.0252(3) Uani 1 1 d . . . . .
N1 N 0.1929(2) 0.47725(9) 0.3798(2) 0.0215(4) Uani 1 1 d . . . . .
C1 C 0.3226(2) 0.57101(10) 0.3257(2) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.2919(2) 0.56278(10) 0.5140(3) 0.0191(4) Uani 1 1 d . . . . .
C3 C 0.2049(2) 0.50389(10) 0.5379(3) 0.0196(4) Uani 1 1 d . . . . .
C4 C 0.2653(2) 0.50848(10) 0.2502(3) 0.0206(4) Uani 1 1 d . . . . .
C5 C 0.2731(3) 0.48347(11) 0.0952(3) 0.0265(5) Uani 1 1 d . . . . .
H5 H 0.326045 0.504750 0.009977 0.032 Uiso 1 1 calc R . . . .
C6 C 0.1972(3) 0.42106(12) 0.0566(3) 0.0321(5) Uani 1 1 d . . . . .
H6A H 0.272585 0.386555 0.066447 0.039 Uiso 1 1 calc R . . . .
H6B H 0.152245 0.421263 -0.061731 0.039 Uiso 1 1 calc R . . . .
C7 C 0.0749(3) 0.40992(12) 0.1808(3) 0.0308(5) Uani 1 1 d . . . . .
H7A H -0.008107 0.440621 0.158376 0.037 Uiso 1 1 calc R . . . .
H7B H 0.032966 0.366861 0.163956 0.037 Uiso 1 1 calc R . . . .
C8 C 0.4921(2) 0.57652(10) 0.3112(3) 0.0209(4) Uani 1 1 d . . . . .
H8 H 0.540065 0.546853 0.240904 0.025 Uiso 1 1 calc R . . . .
C9 C 0.5787(2) 0.62053(11) 0.3911(3) 0.0222(4) Uani 1 1 d . . . . .
H9 H 0.681553 0.622515 0.362707 0.027 Uiso 1 1 calc R . . . .
C10 C 0.5304(2) 0.66508(11) 0.5159(3) 0.0230(4) Uani 1 1 d . . . . .
C11 C 0.4246(2) 0.65758(11) 0.6317(3) 0.0239(4) Uani 1 1 d . . . . .
H11 H 0.411277 0.690757 0.711165 0.029 Uiso 1 1 calc R . . . .
C12 C 0.3305(2) 0.60221(11) 0.6423(2) 0.0215(4) Uani 1 1 d . . . . .
H12 H 0.292384 0.592892 0.750438 0.026 Uiso 1 1 calc R . . . .
C13 C 0.2331(2) 0.62636(10) 0.2441(2) 0.0181(4) Uani 1 1 d . . . . .
C14 C 0.2915(2) 0.66275(11) 0.1154(3) 0.0242(4) Uani 1 1 d . . . . .
H14 H 0.389559 0.653921 0.077970 0.029 Uiso 1 1 calc R . . . .
C15 C 0.2074(3) 0.71195(12) 0.0410(3) 0.0278(5) Uani 1 1 d . . . . .
H15 H 0.248245 0.736683 -0.046569 0.033 Uiso 1 1 calc R . . . .
C16 C 0.0637(3) 0.72502(11) 0.0944(3) 0.0249(5) Uani 1 1 d . . . . .
H16 H 0.006850 0.759115 0.045172 0.030 Uiso 1 1 calc R . . . .
C17 C 0.0041(2) 0.68800(11) 0.2198(3) 0.0240(4) Uani 1 1 d . . . . .
H17 H -0.094906 0.696343 0.255124 0.029 Uiso 1 1 calc R . . . .
C18 C 0.0875(2) 0.63879(10) 0.2944(3) 0.0209(4) Uani 1 1 d . . . . .
H18 H 0.045233 0.613535 0.380022 0.025 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 C10 1.912(2) . ?
O1 N1 1.388(2) . ?
O1 C7 1.455(3) . ?
O2 C3 1.219(3) . ?
N1 C3 1.361(3) . ?
N1 C4 1.396(3) . ?
C1 C2 1.525(3) . ?
C1 C4 1.526(3) . ?
C1 C8 1.517(3) . ?
C1 C13 1.535(3) . ?
C2 C3 1.482(3) . ?
C2 C12 1.338(3) . ?
C4 C5 1.331(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.506(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.513(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 0.9500 . ?
C8 C9 1.341(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.440(3) . ?
C10 C11 1.349(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.443(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 C18 1.394(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(3) . ?
C18 H18 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
N1 O1 C7 109.37(16) . . ?
O1 N1 C4 121.38(17) . . ?
C3 N1 O1 120.91(17) . . ?
C3 N1 C4 116.76(18) . . ?
C2 C1 C4 101.76(17) . . ?
C2 C1 C13 112.07(16) . . ?
C4 C1 C13 110.20(16) . . ?
C8 C1 C2 108.05(16) . . ?
C8 C1 C4 110.38(17) . . ?
C8 C1 C13 113.71(17) . . ?
C3 C2 C1 109.84(17) . . ?
C12 C2 C1 127.2(2) . . ?
C12 C2 C3 122.88(19) . . ?
O2 C3 N1 126.3(2) . . ?
O2 C3 C2 129.26(19) . . ?
N1 C3 C2 104.41(17) . . ?
N1 C4 C1 106.52(17) . . ?
C5 C4 N1 121.7(2) . . ?
C5 C4 C1 131.8(2) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C5 C6 C7 109.5(2) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
O1 C7 C6 110.82(19) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C1 C8 H8 117.9 . . ?
C9 C8 C1 124.24(19) . . ?
C9 C8 H8 117.9 . . ?
C8 C9 H9 117.0 . . ?
C8 C9 C10 126.07(19) . . ?
C10 C9 H9 117.0 . . ?
C9 C10 Br1 113.92(16) . . ?
C11 C10 Br1 117.20(17) . . ?
C11 C10 C9 128.5(2) . . ?
C10 C11 H11 118.0 . . ?
C10 C11 C12 123.9(2) . . ?
C12 C11 H11 118.0 . . ?
C2 C12 C11 126.07(19) . . ?
C2 C12 H12 117.0 . . ?
C11 C12 H12 117.0 . . ?
C14 C13 C1 121.39(18) . . ?
C14 C13 C18 119.10(19) . . ?
C18 C13 C1 119.45(18) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.2(2) . . ?
C17 C18 H18 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C10 C11 C12 -177.38(16) . . . . ?
O1 N1 C3 O2 -7.2(3) . . . . ?
O1 N1 C3 C2 171.55(17) . . . . ?
O1 N1 C4 C1 -176.25(17) . . . . ?
O1 N1 C4 C5 4.4(3) . . . . ?
N1 O1 C7 C6 59.4(2) . . . . ?
N1 C4 C5 C6 2.3(3) . . . . ?
C1 C2 C3 O2 -178.0(2) . . . . ?
C1 C2 C3 N1 3.4(2) . . . . ?
C1 C2 C12 C11 -7.5(3) . . . . ?
C1 C4 C5 C6 -176.8(2) . . . . ?
C1 C8 C9 C10 6.9(4) . . . . ?
C1 C13 C14 C15 178.82(19) . . . . ?
C1 C13 C18 C17 -178.91(18) . . . . ?
C2 C1 C4 N1 8.3(2) . . . . ?
C2 C1 C4 C5 -172.5(2) . . . . ?
C2 C1 C8 C9 -57.7(3) . . . . ?
C2 C1 C13 C14 146.85(19) . . . . ?
C2 C1 C13 C18 -36.0(2) . . . . ?
C3 N1 C4 C1 -7.3(2) . . . . ?
C3 N1 C4 C5 173.4(2) . . . . ?
C3 C2 C12 C11 174.8(2) . . . . ?
C4 N1 C3 O2 -176.2(2) . . . . ?
C4 N1 C3 C2 2.5(2) . . . . ?
C4 C1 C2 C3 -7.2(2) . . . . ?
C4 C1 C2 C12 174.9(2) . . . . ?
C4 C1 C8 C9 -168.2(2) . . . . ?
C4 C1 C13 C14 -100.6(2) . . . . ?
C4 C1 C13 C18 76.5(2) . . . . ?
C4 C5 C6 C7 21.9(3) . . . . ?
C5 C6 C7 O1 -52.7(3) . . . . ?
C7 O1 N1 C3 155.92(19) . . . . ?
C7 O1 N1 C4 -35.6(3) . . . . ?
C8 C1 C2 C3 -123.41(18) . . . . ?
C8 C1 C2 C12 58.6(3) . . . . ?
C8 C1 C4 N1 122.80(18) . . . . ?
C8 C1 C4 C5 -58.0(3) . . . . ?
C8 C1 C13 C14 23.9(3) . . . . ?
C8 C1 C13 C18 -158.95(18) . . . . ?
C8 C9 C10 Br1 -154.76(19) . . . . ?
C8 C9 C10 C11 32.3(4) . . . . ?
C9 C10 C11 C12 -4.6(4) . . . . ?
C10 C11 C12 C2 -25.9(4) . . . . ?
C12 C2 C3 O2 0.1(3) . . . . ?
C12 C2 C3 N1 -178.57(19) . . . . ?
C13 C1 C2 C3 110.53(19) . . . . ?
C13 C1 C2 C12 -67.4(3) . . . . ?
C13 C1 C4 N1 -110.77(18) . . . . ?
C13 C1 C4 C5 68.4(3) . . . . ?
C13 C1 C8 C9 67.4(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C13 C18 C17 -1.7(3) . . . . ?
C14 C15 C16 C17 -1.2(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
C18 C13 C14 C15 1.7(3) . . . . ?

_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_tx165a
_database_code_depnum_ccdc_archive 'CCDC 1883915'
loop_
_audit_author_name
_audit_author_address
'guangyi ren'
;R??'f
China
;
_audit_update_record             
;
2018-12-08 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2018-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Br N O2'
_chemical_formula_sum            'C20 H16 Br N O2'
_chemical_formula_weight         382.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOBr
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.95590(10)
_cell_length_b                   6.80800(10)
_cell_length_c                   30.8630(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.2510(10)
_cell_angle_gamma                90
_cell_volume                     1671.26(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    26008
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      75.2140
_cell_measurement_theta_min      2.8450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.444
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.251
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            29345
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.356
_diffrn_reflns_theta_min         2.864
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -72.00   0.50    0.20    --  -47.20-124.00  22.00   96
  2  ω    -94.00  -9.00   0.50    0.20    --  -47.20 124.00 101.00  170
  3  ω   -107.00 -22.00   0.50    0.20    --  -47.20 147.00 -93.00  170
  4  ω   -120.00 -56.00   0.50    0.20    --  -47.20-147.00-142.00  128
  5  ω     16.00  94.00   0.50    0.20    --   47.20-124.00  22.00  156
  6  ω     28.00 107.00   0.50    0.20    --   47.20-147.00-142.00  158
  7  ω   -168.00 -72.00   0.50    0.30    --  -99.00-124.00  22.00  192
  8  ω   -132.00 -26.00   0.50    0.30    --  -99.00 147.00 -93.00  212
  9  ω     31.00 132.00   0.50    0.30    --  103.25-147.00-142.00  202
 10  ω     62.00 169.00   0.50    0.30    --  103.25 147.00 -93.00  214
 11  ω     78.00 169.00   0.50    0.30    --  103.25 124.00 101.00  182
 12  ω     78.00 169.00   0.50    0.30    --  103.25 124.00 101.00  182
 13  ω   -120.00 -71.00   0.50    0.20    --  -47.20-125.00  90.00   98
 14  ω     35.00 120.00   0.50    0.20    --   47.20  38.00 -90.00  170
 15  ω    -26.00  60.00   0.50    0.20    --   47.20 -38.00 150.00  172
 16  ω     25.00 120.00   0.50    0.20    --   47.20  77.00-180.00  190
 17  ω   -168.00 -76.00   0.50    0.30    --  -99.00 -77.00 120.00  184
 18  ω   -168.00 -81.00   0.50    0.30    --  -99.00 -94.00 -30.00  174
 19  ω   -112.00 -27.00   0.50    0.30    --  -99.00  45.00 -30.00  170
 20  ω   -116.00 -26.00   0.50    0.30    --  -99.00 124.00 101.00  180
 21  ω   -168.00 -82.00   0.50    0.30    --  -99.00 -61.00 -60.00  172
 22  ω   -168.00 -86.00   0.50    0.30    --  -99.00 -30.00  90.00  164
 23  ω   -168.00 -56.00   0.50    0.30    --  -99.00-147.00-142.00  224
 24  ω   -122.00 -26.00   0.50    0.30    --  -99.00  77.00 -60.00  192
 25  ω     91.00 169.00   0.50    0.30    --  103.25  45.00-150.00  156
 26  ω     31.00 120.00   0.50    0.30    --  103.25 -61.00   0.00  178
 27  ω     32.00 116.00   0.50    0.30    --  103.25 -45.00   0.00  168
 28  ω    113.00 169.00   0.50    0.30    --  103.25  45.00   0.00  112
 29  ω     39.00 106.00   0.50    0.30    --  103.25 -61.00-180.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1067757000
_diffrn_orient_matrix_UB_12      -0.1051962000
_diffrn_orient_matrix_UB_13      -0.0352011000
_diffrn_orient_matrix_UB_21      0.0412711000
_diffrn_orient_matrix_UB_22      -0.1994127000
_diffrn_orient_matrix_UB_23      0.0212480000
_diffrn_orient_matrix_UB_31      -0.1561990000
_diffrn_orient_matrix_UB_32      0.0191447000
_diffrn_orient_matrix_UB_33      0.0283423000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3307
_reflns_number_total             3324
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.125
_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)+(0.0227P)²+1.6836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0655
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.26238(3) -0.12682(3) 0.49143(2) 0.03255(8) Uani 1 1 d . . . . .
O1 O 0.49996(16) 0.4571(2) 0.22683(4) 0.0266(3) Uani 1 1 d . . . . .
O2 O 0.18133(15) 0.62239(18) 0.24225(4) 0.0224(3) Uani 1 1 d . . . . .
N1 N 0.29173(17) 0.5464(2) 0.27358(4) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.5196(2) 0.4009(3) 0.30536(5) 0.0200(3) Uani 1 1 d . . . . .
H1 H 0.585127 0.279081 0.306339 0.024 Uiso 1 1 calc R . . . .
C2 C 0.5561(2) 0.5613(3) 0.33840(5) 0.0202(3) Uani 1 1 d . . . . .
H2 H 0.542916 0.695838 0.327537 0.024 Uiso 1 1 calc R . . . .
C3 C 0.3930(2) 0.4416(2) 0.34022(5) 0.0181(3) Uani 1 1 d . . . . .
C4 C 0.2473(2) 0.5390(2) 0.31720(5) 0.0184(3) Uani 1 1 d . . . . .
C5 C 0.1049(2) 0.6164(3) 0.33088(6) 0.0221(4) Uani 1 1 d . . . . .
H5 H 0.073029 0.598688 0.359424 0.027 Uiso 1 1 calc R . . . .
C6 C -0.0050(2) 0.7331(3) 0.29996(6) 0.0262(4) Uani 1 1 d . . . . .
H6A H -0.044893 0.850526 0.314289 0.031 Uiso 1 1 calc R . . . .
H6B H -0.102029 0.655326 0.291146 0.031 Uiso 1 1 calc R . . . .
C7 C 0.0940(2) 0.7903(3) 0.26026(6) 0.0257(4) Uani 1 1 d . . . . .
H7A H 0.017813 0.844713 0.238421 0.031 Uiso 1 1 calc R . . . .
H7B H 0.175188 0.890998 0.268216 0.031 Uiso 1 1 calc R . . . .
C8 C 0.4434(2) 0.4691(2) 0.26324(5) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.6896(2) 0.5346(3) 0.37261(5) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.7345(2) 0.6961(3) 0.39801(6) 0.0297(4) Uani 1 1 d . . . . .
H10 H 0.682920 0.816687 0.392886 0.036 Uiso 1 1 calc R . . . .
C11 C 0.8558(3) 0.6791(4) 0.43096(6) 0.0383(5) Uani 1 1 d . . . . .
H11 H 0.885047 0.788013 0.447677 0.046 Uiso 1 1 calc R . . . .
C12 C 0.9329(2) 0.5002(4) 0.43885(6) 0.0377(5) Uani 1 1 d . . . . .
H12 H 1.013433 0.488389 0.460995 0.045 Uiso 1 1 calc R . . . .
C13 C 0.8901(2) 0.3388(3) 0.41374(6) 0.0346(5) Uani 1 1 d . . . . .
H13 H 0.942345 0.218654 0.418901 0.042 Uiso 1 1 calc R . . . .
C14 C 0.7687(2) 0.3559(3) 0.38073(6) 0.0293(4) Uani 1 1 d . . . . .
H14 H 0.740316 0.246791 0.363978 0.035 Uiso 1 1 calc R . . . .
C15 C 0.3600(2) 0.3038(3) 0.37686(5) 0.0180(3) Uani 1 1 d . . . . .
C16 C 0.3606(2) 0.3721(3) 0.41945(6) 0.0221(4) Uani 1 1 d . . . . .
H16 H 0.381281 0.504313 0.425004 0.027 Uiso 1 1 calc R . . . .
C17 C 0.3307(2) 0.2455(3) 0.45363(5) 0.0235(4) Uani 1 1 d . . . . .
H17 H 0.331520 0.291535 0.482003 0.028 Uiso 1 1 calc R . . . .
C18 C 0.2996(2) 0.0500(3) 0.44481(6) 0.0232(4) Uani 1 1 d . . . . .
C19 C 0.2972(2) -0.0216(3) 0.40282(6) 0.0268(4) Uani 1 1 d . . . . .
H19 H 0.275255 -0.153622 0.397404 0.032 Uiso 1 1 calc R . . . .
C20 C 0.3281(2) 0.1066(3) 0.36889(6) 0.0249(4) Uani 1 1 d . . . . .
H20 H 0.327338 0.059814 0.340576 0.030 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 C18 1.9041(17) . ?
O1 C8 1.222(2) . ?
O2 N1 1.3917(17) . ?
O2 C7 1.455(2) . ?
N1 C4 1.400(2) . ?
N1 C8 1.361(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.518(2) . ?
C1 C3 1.515(2) . ?
C1 C8 1.496(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.534(2) . ?
C2 C9 1.492(2) . ?
C3 C4 1.500(2) . ?
C3 C15 1.497(2) . ?
C4 C5 1.327(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.507(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.521(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.392(3) . ?
C9 C14 1.390(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(2) . ?
C15 C20 1.387(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(3) . ?
C18 C19 1.384(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.389(3) . ?
C20 H20 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
N1 O2 C7 109.02(12) . . ?
O2 N1 C4 120.85(13) . . ?
C8 N1 O2 122.03(13) . . ?
C8 N1 C4 117.07(14) . . ?
C2 C1 H1 119.6 . . ?
C3 C1 H1 119.6 . . ?
C3 C1 C2 60.78(11) . . ?
C8 C1 H1 119.6 . . ?
C8 C1 C2 115.38(14) . . ?
C8 C1 C3 107.29(14) . . ?
C1 C2 H2 115.1 . . ?
C1 C2 C3 59.52(11) . . ?
C3 C2 H2 115.1 . . ?
C9 C2 C1 120.69(15) . . ?
C9 C2 H2 115.1 . . ?
C9 C2 C3 119.93(14) . . ?
C1 C3 C2 59.70(11) . . ?
C4 C3 C1 105.25(13) . . ?
C4 C3 C2 113.12(14) . . ?
C15 C3 C1 123.50(14) . . ?
C15 C3 C2 121.51(14) . . ?
C15 C3 C4 119.25(14) . . ?
N1 C4 C3 105.23(13) . . ?
C5 C4 N1 121.77(15) . . ?
C5 C4 C3 132.93(15) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.73(16) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C5 C6 C7 109.95(14) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
O2 C7 C6 111.53(15) . . ?
O2 C7 H7A 109.3 . . ?
O2 C7 H7B 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
O1 C8 N1 125.99(16) . . ?
O1 C8 C1 128.88(16) . . ?
N1 C8 C1 105.12(13) . . ?
C10 C9 C2 118.18(17) . . ?
C14 C9 C2 123.13(17) . . ?
C14 C9 C10 118.68(17) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.87(18) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(2) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.6(2) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C3 120.40(15) . . ?
C20 C15 C3 120.46(15) . . ?
C20 C15 C16 119.15(16) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.82(16) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.86(16) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 Br1 119.40(13) . . ?
C17 C18 C19 121.54(16) . . ?
C19 C18 Br1 119.05(14) . . ?
C18 C19 H19 120.5 . . ?
C18 C19 C20 119.04(17) . . ?
C20 C19 H19 120.5 . . ?
C15 C20 C19 120.60(17) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 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 C18 C19 C20 -178.59(14) . . . . ?
O2 N1 C4 C3 177.64(14) . . . . ?
O2 N1 C4 C5 -5.0(2) . . . . ?
O2 N1 C8 O1 0.2(3) . . . . ?
O2 N1 C8 C1 -178.69(14) . . . . ?
N1 O2 C7 C6 -59.67(17) . . . . ?
N1 C4 C5 C6 -6.2(3) . . . . ?
C1 C2 C3 C4 -94.69(15) . . . . ?
C1 C2 C3 C15 113.05(17) . . . . ?
C1 C2 C9 C10 170.81(16) . . . . ?
C1 C2 C9 C14 -10.3(3) . . . . ?
C1 C3 C4 N1 0.91(17) . . . . ?
C1 C3 C4 C5 -176.01(19) . . . . ?
C1 C3 C15 C16 130.03(18) . . . . ?
C1 C3 C15 C20 -50.2(2) . . . . ?
C2 C1 C3 C4 108.19(15) . . . . ?
C2 C1 C3 C15 -109.83(17) . . . . ?
C2 C1 C8 O1 117.8(2) . . . . ?
C2 C1 C8 N1 -63.41(18) . . . . ?
C2 C3 C4 N1 64.02(17) . . . . ?
C2 C3 C4 C5 -112.9(2) . . . . ?
C2 C3 C15 C16 57.7(2) . . . . ?
C2 C3 C15 C20 -122.46(18) . . . . ?
C2 C9 C10 C11 178.71(17) . . . . ?
C2 C9 C14 C13 -178.61(16) . . . . ?
C3 C1 C2 C9 108.90(17) . . . . ?
C3 C1 C8 O1 -176.96(17) . . . . ?
C3 C1 C8 N1 1.87(18) . . . . ?
C3 C2 C9 C10 -119.00(18) . . . . ?
C3 C2 C9 C14 59.9(2) . . . . ?
C3 C4 C5 C6 170.31(18) . . . . ?
C3 C15 C16 C17 -179.82(16) . . . . ?
C3 C15 C20 C19 -179.90(16) . . . . ?
C4 N1 C8 O1 177.48(17) . . . . ?
C4 N1 C8 C1 -1.4(2) . . . . ?
C4 C3 C15 C16 -92.90(19) . . . . ?
C4 C3 C15 C20 86.9(2) . . . . ?
C4 C5 C6 C7 -16.0(2) . . . . ?
C5 C6 C7 O2 49.0(2) . . . . ?
C7 O2 N1 C4 38.1(2) . . . . ?
C7 O2 N1 C8 -144.75(16) . . . . ?
C8 N1 C4 C3 0.3(2) . . . . ?
C8 N1 C4 C5 177.65(16) . . . . ?
C8 C1 C2 C3 96.41(16) . . . . ?
C8 C1 C2 C9 -154.69(15) . . . . ?
C8 C1 C3 C2 -109.89(15) . . . . ?
C8 C1 C3 C4 -1.71(18) . . . . ?
C8 C1 C3 C15 140.28(16) . . . . ?
C9 C2 C3 C1 -110.15(18) . . . . ?
C9 C2 C3 C4 155.16(15) . . . . ?
C9 C2 C3 C15 2.9(2) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C9 C14 C13 0.2(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C9 0.1(3) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C15 C3 C4 N1 -143.03(15) . . . . ?
C15 C3 C4 C5 40.1(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C15 C20 C19 -0.1(3) . . . . ?
C16 C17 C18 Br1 178.86(13) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 -0.3(3) . . . . ?
C20 C15 C16 C17 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.532
_oxdiff_exptl_absorpt_empirical_full_min 0.750
####################################################################### 
# 
# 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_tx560
_database_code_depnum_ccdc_archive 'CCDC 1911414'
loop_
_audit_author_name
_audit_author_address
GRS
;Beijing
China
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2019-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 F3 N O2'
_chemical_formula_sum            'C19 H16 F3 N O2'
_chemical_formula_weight         347.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.42120(10)
_cell_length_b                   10.76290(10)
_cell_length_c                   18.7421(2)
_cell_angle_alpha                94.9390(10)
_cell_angle_beta                 96.7790(10)
_cell_angle_gamma                110.5760(10)
_cell_volume                     1750.05(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    45791
_cell_measurement_temperature    169.99(13)
_cell_measurement_theta_max      75.2870
_cell_measurement_theta_min      2.4290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.211
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0074
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            63483
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.509
_diffrn_reflns_theta_min         2.397
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -28.00   0.50    0.05    --  -47.20 159.00 -14.00  176
  2  ω   -120.00 -48.00   0.50    0.05    --  -47.20-159.00 -46.00  144
  3  ω    -91.00  -5.00   0.50    0.05    --  -47.20 118.00-167.00  172
  4  ω     12.00  91.00   0.50    0.05    --   47.20-118.00 106.00  158
  5  ω     34.00 116.00   0.50    0.05    --   47.20-159.00 -46.00  164
  6  ω     54.00 120.00   0.50    0.05    --   47.20 159.00 -14.00  132
  7  ω   -140.00 -28.00   0.50    0.05    --  -99.00 159.00 -14.00  224
  8  ω   -168.00 -75.00   0.50    0.05    --  -99.00-118.00 106.00  186
  9  ω   -112.00 -26.00   0.50    0.05    --  -99.00 118.00-167.00  172
 10  ω   -164.00 -48.00   0.50    0.05    --  -99.00-159.00 -46.00  232
 11  ω     54.00 164.00   0.50    0.05    --  103.25 159.00 -14.00  220
 12  ω     75.00 138.00   0.50    0.05    --  103.25-159.00 -46.00  126
 13  ω     54.00  80.00   0.50    0.05    --  103.25-118.00 106.00   52
 14  ω    107.00 133.00   0.50    0.05    --  103.25 118.00-167.00   52
 15  ω    -57.00 -31.00   0.50    0.05    --   14.00 163.00 -92.50   52
 16  ω     -7.00  21.00   0.50    0.05    --   26.00 100.00  14.75   56
 17  ω      2.00  27.00   0.50    0.05    --   34.00  97.00 151.07   50
 18  ω      8.00  36.00   0.50    0.05    --   38.00  93.00 -75.06   56
 19  ω     12.00  37.00   0.50    0.05    --   38.00  87.00  49.16   50
 20  ω    -82.00 -36.00   0.50    0.05    --  -47.20 -41.00 -25.46   92
 21  ω    -49.00 -24.00   0.50    0.05    --  -47.20 -77.00 -90.00   50
 22  ω   -121.00 -56.00   0.50    0.05    --  -47.20 -19.00   0.00  130
 23  ω   -105.00 -79.00   0.50    0.05    --  -47.20 -77.00 -90.00   52
 24  ω     87.00 117.00   0.50    0.05    --   47.20  19.00 120.00   60
 25  ω     77.00 116.00   0.50    0.05    --   47.20  38.00-180.00   78
 26  ω     38.00  70.00   0.50    0.05    --   47.20  38.00-180.00   64
 27  ω     41.00  80.00   0.50    0.05    --   47.20  19.00 120.00   78
 28  ω     25.00  54.00   0.50    0.05    --   50.00  82.00 152.43   58
 29  ω     26.00  55.00   0.50    0.05    --   50.00  81.00-165.49   58
 30  ω     29.00  93.00   0.50    0.05    --   50.00  77.00   4.74  128
 31  ω    -57.00 -31.00   0.50    0.05    --  -54.00 -77.00  43.27   52
 32  ω     34.00  60.00   0.50    0.05    --   54.00  74.00-133.02   52
 33  ω     33.00  59.00   0.50    0.05    --   54.00  77.00 121.08   52
 34  ω     30.00  56.00   0.50    0.05    --   54.00  81.00  76.51   52
 35  ω     34.00  65.00   0.50    0.05    --   58.00  80.00-115.73   62
 36  ω     33.00  59.00   0.50    0.05    --   58.00  83.00 -12.68   52
 37  ω     36.00  73.00   0.50    0.05    --   58.00  78.00 -76.14   74
 38  ω     38.00  64.00   0.50    0.05    --   58.00  75.00  74.85   52
 39  ω    -79.00 -41.00   0.50    0.05    --  -62.00 -73.00-137.52   76
 40  ω    -64.00 -38.00   0.50    0.05    --  -62.00 -82.00 -93.44   52
 41  ω     43.00  68.00   0.50    0.05    --   62.00  77.00  76.64   50
 42  ω     38.00  72.00   0.50    0.05    --   62.00  80.00  34.93   68
 43  ω     40.00  78.00   0.50    0.05    --   62.00  76.00 -65.67   76
 44  ω     40.00  66.00   0.50    0.05    --   62.00  75.00 176.30   52
 45  ω    -75.00 -48.00   0.50    0.05    --  -66.00 -66.00-178.22   54
 46  ω     42.00  69.00   0.50    0.05    --   66.00  79.00 -44.58   54
 47  ω     51.00  77.00   0.50    0.05    --   66.00  66.00  97.02   52
 48  ω     43.00  69.00   0.50    0.05    --   66.00  79.00   7.69   52
 49  ω    -79.00 -53.00   0.50    0.05    --  -70.00 -63.00 171.30   52
 50  ω    -76.00 -49.00   0.50    0.05    --  -70.00 -80.00  33.02   54
 51  ω    -79.00 -48.00   0.50    0.05    --  -70.00 -76.00-136.03   62
 52  ω    -96.00 -54.00   0.50    0.05    --  -70.00 -62.00  61.73   84
 53  ω     47.00  74.00   0.50    0.05    --   70.00  79.00 123.95   54
 54  ω    -78.00 -51.00   0.50    0.05    --  -74.00 -83.00 -52.97   54
 55  ω    -75.00 -49.00   0.50    0.05    --  -74.00 -82.00 128.72   52
 56  ω    -75.00 -49.00   0.50    0.05    --  -74.00 -81.00-106.53   52
 57  ω    -85.00 -59.00   0.50    0.05    --  -74.00 -62.00 167.65   52
 58  ω    -76.00 -50.00   0.50    0.05    --  -74.00 -79.00  50.32   52
 59  ω    -78.00 -52.00   0.50    0.05    --  -78.00 -83.00  20.08   52
 60  ω    -80.00 -53.00   0.50    0.05    --  -78.00 -81.00 -12.08   54
 61  ω    -77.00 -52.00   0.50    0.05    --  -78.00 -83.00 145.40   50
 62  ω    -85.00 -59.00   0.50    0.05    --  -82.00 -77.00 178.84   52
 63  ω    -82.00 -56.00   0.50    0.05    --  -82.00 -83.00 129.62   52
 64  ω    -87.00 -60.00   0.50    0.05    --  -82.00 -74.00 102.75   54
 65  ω    -81.00 -56.00   0.50    0.05    --  -82.00 -83.00 -96.27   50
 66  ω    -91.00 -65.00   0.50    0.05    --  -82.00 -63.00-163.74   52
 67  ω   -154.00 -59.00   0.50    0.05    --  -82.00 -76.00 -36.85  190
 68  ω    -90.00 -57.00   0.50    0.05    --  -82.00 -81.00 -79.40   66
 69  ω    -86.00 -60.00   0.50    0.05    --  -86.00 -83.00  53.80   52
 70  ω   -152.00-126.00   0.50    0.05    --  -86.00 -83.00  53.80   52
 71  ω    -92.00 -64.00   0.50    0.05    --  -86.00 -74.00   3.93   56
 72  ω   -157.00-131.00   0.50    0.05    --  -86.00 -74.00   3.93   52
 73  ω   -159.00 -64.00   0.50    0.05    --  -86.00 -74.00 -88.34  190
 74  ω   -161.00 -73.00   0.50    0.05    --  -90.00 -62.00  64.22  176
 75  ω   -100.00 -73.00   0.50    0.05    --  -90.00 -62.00-164.15   54
 76  ω    -92.00 -67.00   0.50    0.05    --  -90.00 -76.00  99.75   50
 77  ω   -119.00 -94.00   0.50    0.05    --  -90.00 -76.00  99.75   50
 78  ω    -98.00 -71.00   0.50    0.05    --  -90.00 -68.00 117.61   54
 79  ω   -151.00 -71.00   0.50    0.05    --  -90.00 -67.00-130.25  160
 80  ω   -114.00 -72.00   0.50    0.05    --  -90.00 -64.00  43.29   84
 81  ω   -154.00-128.00   0.50    0.05    --  -90.00 -69.00 155.39   52
 82  ω   -102.00 -70.00   0.50    0.05    --  -90.00 -69.00 155.39   64
 83  ω    -95.00 -68.00   0.50    0.05    --  -90.00 -76.00 -92.78   54
 84  ω   -165.00 -80.00   0.50    0.05    --  -94.00 -53.00-103.71  170
 85  ω   -167.00 -75.00   0.50    0.05    --  -94.00 -68.00 146.72  184
 86  ω    -98.00 -71.00   0.50    0.05    --  -94.00 -76.00 123.06   54
 87  ω   -151.00-124.00   0.50    0.05    --  -94.00 -76.00 123.06   54
 88  ω   -102.00 -74.00   0.50    0.05    --  -98.00 -80.00-161.80   56
 89  ω   -157.00-113.00   0.50    0.05    --  -98.00 -80.00-161.80   88
 90  ω   -121.00 -28.00   0.50    0.05    --  -99.00  77.00  30.00  186
 91  ω   -117.00 -54.00   0.50    0.05    --  -99.00 125.00  60.00  126
 92  ω   -167.00 -78.00   0.50    0.05    --  -99.00 -73.00-145.26  178
 93  ω   -167.00 -80.00   0.50    0.05    --  -99.00 -68.00 -53.26  174
 94  ω   -111.00 -74.00   0.50    0.05    --  -99.00 -81.00 104.35   74
 95  ω   -148.00 -76.00   0.50    0.05    --  -99.00 -77.00   0.00  144
 96  ω   -107.00 -75.00   0.50    0.05    --  -99.00 -79.00  32.72   64
 97  ω   -168.00 -77.00   0.50    0.05    --  -99.00 -78.00  47.24  182
 98  ω   -105.00 -76.00   0.50    0.05    --  -99.00 -78.00 -98.27   58
 99  ω   -123.00 -82.00   0.50    0.05    --  -99.00 -61.00 -30.00   82
100  ω   -117.00 -27.00   0.50    0.05    --  -99.00 125.00-150.00  180
101  ω   -168.00 -79.00   0.50    0.05    --  -99.00 -70.00 128.32  178
102  ω   -168.00 -76.00   0.50    0.05    --  -99.00 -77.00 -30.00  184
103  ω   -167.00-141.00   0.50    0.05    --  -99.00-125.00-120.00   52
104  ω     67.00 117.00   0.50    0.05    --  103.25 -61.00-120.00  100
105  ω     32.00  60.00   0.50    0.05    --  103.25 -61.00-120.00   56
106  ω     38.00 115.00   0.50    0.05    --  103.25 -45.00  90.00  154
107  ω     71.00  97.00   0.50    0.05    --  103.25 -94.00  30.00   52
108  ω     43.00  69.00   0.50    0.05    --  103.25 -94.00  30.00   52
109  ω     62.00 113.00   0.50    0.05    --  103.25 -45.00-120.00  102
110  ω     54.00 100.00   0.50    0.05    --  103.25 -61.00  90.00   92
111  ω     81.00 108.00   0.50    0.05    --  103.25  77.00-180.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0089942000
_diffrn_orient_matrix_UB_12      0.0614342000
_diffrn_orient_matrix_UB_13      -0.0708825000
_diffrn_orient_matrix_UB_21      0.0824459000
_diffrn_orient_matrix_UB_22      0.1414147000
_diffrn_orient_matrix_UB_23      0.0427214000
_diffrn_orient_matrix_UB_31      0.1562697000
_diffrn_orient_matrix_UB_32      -0.0072006000
_diffrn_orient_matrix_UB_33      -0.0115772000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6582
_reflns_number_total             6919
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6919
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.055
_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)+(0.0491P)²+0.6120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1081
_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.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C18A(H18C,H18D)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C15(H15), N1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A),
  C6A(H6A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A), C15A(H15A)
2.c X=CH2 refined with riding coordinates:
 C16(H16A,H16B), C16A(H16C,H16D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.3002(2) 0.10614(14) 0.74637(7) 0.1052(5) Uani 1 1 d . . . . .
F2 F 0.17212(15) -0.05158(12) 0.65947(8) 0.0897(4) Uani 1 1 d . . . . .
F3 F 0.39988(19) -0.03060(13) 0.70417(10) 0.1128(6) Uani 1 1 d . . . . .
O1 O 0.41874(10) 0.38294(10) 0.67956(5) 0.0402(2) Uani 1 1 d . . . . .
O2 O 0.52044(11) 0.22254(9) 0.66185(6) 0.0423(2) Uani 1 1 d . . . . .
N1 N 0.66252(12) 0.41432(11) 0.72996(6) 0.0353(2) Uani 1 1 d . . . . .
H1 H 0.731789 0.379240 0.731894 0.042 Uiso 1 1 calc R . . . .
C1 C 0.72965(14) 0.78258(12) 0.77342(6) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.61752(15) 0.79529(14) 0.81229(7) 0.0378(3) Uani 1 1 d . . . . .
H2 H 0.532844 0.719790 0.815554 0.045 Uiso 1 1 calc R . . . .
C3 C 0.63054(18) 0.91931(15) 0.84625(8) 0.0458(3) Uani 1 1 d . . . . .
H3 H 0.553560 0.926898 0.871130 0.055 Uiso 1 1 calc R . . . .
C4 C 0.75751(19) 1.03159(15) 0.84323(8) 0.0472(3) Uani 1 1 d . . . . .
H4 H 0.766464 1.114637 0.866295 0.057 Uiso 1 1 calc R . . . .
C5 C 0.87107(18) 1.02024(14) 0.80589(8) 0.0455(3) Uani 1 1 d . . . . .
H5 H 0.957744 1.095434 0.804740 0.055 Uiso 1 1 calc R . . . .
C6 C 0.85644(16) 0.89714(14) 0.77009(7) 0.0381(3) Uani 1 1 d . . . . .
H6 H 0.931747 0.890857 0.743628 0.046 Uiso 1 1 calc R . . . .
C7 C 0.71332(14) 0.65087(13) 0.73397(6) 0.0310(3) Uani 1 1 d . . . . .
C8 C 0.71149(15) 0.64504(13) 0.65415(7) 0.0355(3) Uani 1 1 d . . . . .
C9 C 0.61887(18) 0.69659(15) 0.61256(8) 0.0442(3) Uani 1 1 d . . . . .
H9 H 0.558738 0.735750 0.634760 0.053 Uiso 1 1 calc R . . . .
C10 C 0.6156(2) 0.68994(19) 0.53810(9) 0.0586(4) Uani 1 1 d . . . . .
H10 H 0.551493 0.722708 0.510485 0.070 Uiso 1 1 calc R . . . .
C11 C 0.7069(3) 0.6351(2) 0.50486(9) 0.0686(5) Uani 1 1 d . . . . .
H11 H 0.704730 0.630943 0.454955 0.082 Uiso 1 1 calc R . . . .
C12 C 0.8012(3) 0.5865(2) 0.54578(10) 0.0714(6) Uani 1 1 d . . . . .
H12 H 0.864063 0.550700 0.523537 0.086 Uiso 1 1 calc R . . . .
C13 C 0.8033(2) 0.59053(19) 0.62001(8) 0.0533(4) Uani 1 1 d . . . . .
H13 H 0.866682 0.556407 0.647135 0.064 Uiso 1 1 calc R . . . .
C14 C 0.69866(13) 0.54404(12) 0.76916(7) 0.0313(3) Uani 1 1 d . . . . .
C15 C 0.71900(15) 0.54906(14) 0.84800(7) 0.0367(3) Uani 1 1 d . . . . .
H15 H 0.754877 0.633104 0.875710 0.044 Uiso 1 1 calc R . . . .
C16 C 0.69042(18) 0.44349(17) 0.88314(9) 0.0493(4) Uani 1 1 d . . . . .
H16A H 0.654400 0.357713 0.857374 0.059 Uiso 1 1 calc R . . . .
H16B H 0.706368 0.455099 0.933581 0.059 Uiso 1 1 calc R . . . .
C17 C 0.52533(14) 0.34564(12) 0.69049(7) 0.0315(3) Uani 1 1 d . . . . .
C18 C 0.37235(17) 0.12784(14) 0.63197(8) 0.0448(3) Uani 1 1 d . . . . .
H18A H 0.378470 0.075505 0.588440 0.054 Uiso 1 1 calc R . . . .
H18B H 0.303472 0.174166 0.618874 0.054 Uiso 1 1 calc R . . . .
C19 C 0.3123(2) 0.03813(18) 0.68587(11) 0.0637(5) Uani 1 1 d . . . . .
F1A F -0.18873(17) 0.26082(13) 0.56209(7) 0.0888(4) Uani 1 1 d . . . . .
F2A F -0.11492(17) 0.11236(15) 0.51297(6) 0.0933(4) Uani 1 1 d . . . . .
F3A F -0.34409(14) 0.05599(14) 0.53658(7) 0.0872(4) Uani 1 1 d . . . . .
O1A O -0.09984(10) 0.31560(10) 0.73451(6) 0.0419(2) Uani 1 1 d . . . . .
O2A O 0.00193(11) 0.19815(9) 0.66325(5) 0.0407(2) Uani 1 1 d . . . . .
N1A N 0.15108(12) 0.39868(11) 0.72007(6) 0.0343(2) Uani 1 1 d . . . . .
H1A H 0.221856 0.378132 0.702859 0.041 Uiso 1 1 calc R . . . .
C1A C 0.21965(13) 0.67436(11) 0.87518(6) 0.0283(2) Uani 1 1 d . . . . .
C2A C 0.13945(15) 0.75567(12) 0.85454(7) 0.0335(3) Uani 1 1 d . . . . .
H2A H 0.067979 0.728801 0.812173 0.040 Uiso 1 1 calc R . . . .
C3A C 0.16528(16) 0.87665(13) 0.89669(7) 0.0375(3) Uani 1 1 d . . . . .
H3A H 0.112337 0.930877 0.882020 0.045 Uiso 1 1 calc R . . . .
C4A C 0.26942(16) 0.91647(12) 0.96033(7) 0.0368(3) Uani 1 1 d . . . . .
H4A H 0.286622 0.997440 0.988438 0.044 Uiso 1 1 calc R . . . .
C5A C 0.34809(15) 0.83572(13) 0.98218(7) 0.0349(3) Uani 1 1 d . . . . .
H5A H 0.417528 0.862163 1.025227 0.042 Uiso 1 1 calc R . . . .
C6A C 0.32371(14) 0.71575(12) 0.94015(7) 0.0310(3) Uani 1 1 d . . . . .
H6A H 0.377007 0.662028 0.955221 0.037 Uiso 1 1 calc R . . . .
C7A C 0.19455(13) 0.54337(11) 0.83212(7) 0.0287(2) Uani 1 1 d . . . . .
C8A C 0.17687(13) 0.43059(11) 0.87546(7) 0.0294(2) Uani 1 1 d . . . . .
C9A C 0.27141(16) 0.35642(13) 0.87285(8) 0.0391(3) Uani 1 1 d . . . . .
H9A H 0.342513 0.372870 0.841033 0.047 Uiso 1 1 calc R . . . .
C10A C 0.26019(19) 0.25802(15) 0.91746(9) 0.0482(4) Uani 1 1 d . . . . .
H10A H 0.324105 0.209174 0.915438 0.058 Uiso 1 1 calc R . . . .
C11A C 0.15484(19) 0.23213(14) 0.96481(8) 0.0470(3) Uani 1 1 d . . . . .
H11A H 0.147997 0.166367 0.994752 0.056 Uiso 1 1 calc R . . . .
C12A C 0.05962(17) 0.30458(13) 0.96743(8) 0.0418(3) Uani 1 1 d . . . . .
H12A H -0.012206 0.286908 0.998896 0.050 Uiso 1 1 calc R . . . .
C13A C 0.07082(15) 0.40327(12) 0.92340(7) 0.0344(3) Uani 1 1 d . . . . .
H13A H 0.006836 0.451986 0.925810 0.041 Uiso 1 1 calc R . . . .
C14A C 0.19077(13) 0.52893(12) 0.75960(7) 0.0307(3) Uani 1 1 d . . . . .
C15A C 0.22792(15) 0.63773(14) 0.71520(7) 0.0369(3) Uani 1 1 d . . . . .
H15A H 0.270143 0.724987 0.739186 0.044 Uiso 1 1 calc R . . . .
C16A C 0.2060(2) 0.62150(17) 0.64349(8) 0.0503(4) Uani 1 1 d . . . . .
H16C H 0.164049 0.535723 0.617609 0.060 Uiso 1 1 calc R . . . .
H16D H 0.232628 0.695857 0.618927 0.060 Uiso 1 1 calc R . . . .
C17A C 0.00895(14) 0.30792(12) 0.70882(7) 0.0318(3) Uani 1 1 d . . . . .
C18A C -0.14902(18) 0.10600(14) 0.63497(8) 0.0468(3) Uani 1 1 d . . . . .
H18C H -0.219731 0.114141 0.667103 0.056 Uiso 1 1 calc R . . . .
H18D H -0.150496 0.015101 0.631708 0.056 Uiso 1 1 calc R . . . .
C19A C -0.1976(2) 0.13483(19) 0.56176(9) 0.0605(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 C19 1.334(2) . ?
F2 C19 1.337(2) . ?
F3 C19 1.324(3) . ?
O1 C17 1.2085(15) . ?
O2 C17 1.3691(15) . ?
O2 C18 1.4201(17) . ?
N1 C14 1.4266(16) . ?
N1 C17 1.3315(16) . ?
C1 C2 1.3898(19) . ?
C1 C6 1.3952(18) . ?
C1 C7 1.4897(17) . ?
C2 C3 1.3865(19) . ?
C3 C4 1.381(2) . ?
C4 C5 1.380(2) . ?
C5 C6 1.386(2) . ?
C7 C8 1.4898(17) . ?
C7 C14 1.3478(18) . ?
C8 C9 1.390(2) . ?
C8 C13 1.387(2) . ?
C9 C10 1.387(2) . ?
C10 C11 1.377(3) . ?
C11 C12 1.373(3) . ?
C12 C13 1.386(2) . ?
C14 C15 1.4614(18) . ?
C15 C16 1.324(2) . ?
C18 C19 1.481(2) . ?
F1A C19A 1.328(2) . ?
F2A C19A 1.328(2) . ?
F3A C19A 1.342(2) . ?
O1A C17A 1.2077(16) . ?
O2A C17A 1.3738(15) . ?
O2A C18A 1.4238(17) . ?
N1A C14A 1.4288(15) . ?
N1A C17A 1.3304(16) . ?
C1A C2A 1.3930(17) . ?
C1A C6A 1.4001(17) . ?
C1A C7A 1.4898(16) . ?
C2A C3A 1.3905(18) . ?
C3A C4A 1.3816(19) . ?
C4A C5A 1.3838(19) . ?
C5A C6A 1.3835(17) . ?
C7A C8A 1.4902(17) . ?
C7A C14A 1.3494(17) . ?
C8A C9A 1.3915(18) . ?
C8A C13A 1.3938(18) . ?
C9A C10A 1.388(2) . ?
C10A C11A 1.381(2) . ?
C11A C12A 1.382(2) . ?
C12A C13A 1.3831(19) . ?
C14A C15A 1.4611(18) . ?
C15A C16A 1.322(2) . ?
C18A C19A 1.488(2) . ?

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
C17 O2 C18 115.82(11) . . ?
C17 N1 C14 122.31(10) . . ?
C2 C1 C6 118.51(12) . . ?
C2 C1 C7 121.13(11) . . ?
C6 C1 C7 120.33(12) . . ?
C3 C2 C1 120.71(13) . . ?
C4 C3 C2 120.15(14) . . ?
C5 C4 C3 119.82(14) . . ?
C4 C5 C6 120.23(13) . . ?
C5 C6 C1 120.54(13) . . ?
C1 C7 C8 115.94(11) . . ?
C14 C7 C1 121.19(11) . . ?
C14 C7 C8 122.86(11) . . ?
C9 C8 C7 120.21(12) . . ?
C13 C8 C7 121.09(12) . . ?
C13 C8 C9 118.69(13) . . ?
C10 C9 C8 120.33(15) . . ?
C11 C10 C9 120.35(16) . . ?
C12 C11 C10 119.65(15) . . ?
C11 C12 C13 120.47(17) . . ?
C12 C13 C8 120.49(16) . . ?
N1 C14 C15 114.63(11) . . ?
C7 C14 N1 120.77(11) . . ?
C7 C14 C15 124.60(12) . . ?
C16 C15 C14 125.20(14) . . ?
O1 C17 O2 123.21(11) . . ?
O1 C17 N1 126.98(12) . . ?
N1 C17 O2 109.81(11) . . ?
O2 C18 C19 109.54(13) . . ?
F1 C19 F2 106.98(17) . . ?
F1 C19 C18 111.69(15) . . ?
F2 C19 C18 110.93(16) . . ?
F3 C19 F1 107.92(18) . . ?
F3 C19 F2 106.74(15) . . ?
F3 C19 C18 112.30(18) . . ?
C17A O2A C18A 115.13(11) . . ?
C17A N1A C14A 122.60(10) . . ?
C2A C1A C6A 118.44(11) . . ?
C2A C1A C7A 122.45(11) . . ?
C6A C1A C7A 119.08(11) . . ?
C3A C2A C1A 120.61(12) . . ?
C4A C3A C2A 120.14(12) . . ?
C3A C4A C5A 119.92(12) . . ?
C6A C5A C4A 120.17(12) . . ?
C5A C6A C1A 120.70(11) . . ?
C1A C7A C8A 114.84(10) . . ?
C14A C7A C1A 122.39(11) . . ?
C14A C7A C8A 122.76(11) . . ?
C9A C8A C7A 121.34(11) . . ?
C9A C8A C13A 118.55(12) . . ?
C13A C8A C7A 119.97(11) . . ?
C10A C9A C8A 120.38(13) . . ?
C11A C10A C9A 120.49(14) . . ?
C10A C11A C12A 119.58(13) . . ?
C11A C12A C13A 120.21(13) . . ?
C12A C13A C8A 120.79(12) . . ?
N1A C14A C15A 114.36(11) . . ?
C7A C14A N1A 119.98(11) . . ?
C7A C14A C15A 125.64(11) . . ?
C16A C15A C14A 124.94(13) . . ?
O1A C17A O2A 123.23(11) . . ?
O1A C17A N1A 127.12(11) . . ?
N1A C17A O2A 109.63(10) . . ?
O2A C18A C19A 109.41(14) . . ?
F1A C19A F3A 107.11(16) . . ?
F1A C19A C18A 112.52(14) . . ?
F2A C19A F1A 107.05(18) . . ?
F2A C19A F3A 106.47(14) . . ?
F2A C19A C18A 113.00(17) . . ?
F3A C19A C18A 110.32(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1A 0.86 1.93 2.7912(14) 174.8 1_655 yes
N1A H1A O1 0.86 1.94 2.7738(14) 163.1 . yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.221
_oxdiff_exptl_absorpt_empirical_full_min 0.845
