# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_cu_20241841_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2l9dkw
_database_code_depnum_ccdc_archive 'CCDC 2392318'
loop_
_audit_author_name
_audit_author_address
'liang hanyu'
;shanghai normal university
China
;
_audit_update_record             
;
2024-10-19 deposited with the CCDC.	2025-01-03 downloaded from the CCDC.
;
_audit_creation_date             2024-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 F3 N O2'
_chemical_formula_sum            'C15 H14 F3 N O2'
_chemical_formula_weight         297.27
_chemical_absolute_configuration rmad
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8059(3)
_cell_length_b                   9.5499(4)
_cell_length_c                   22.0878(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1435.61(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.406
_cell_measurement_theta_min      5.045
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.888
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1771 before and 0.0795 after correction.
The Ratio of minimum to maximum transmission is 0.6138.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12166
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.688
_diffrn_reflns_theta_min         5.045
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker d8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2682
_reflns_number_total             2907
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1052 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+0.1839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1078
_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:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C5(H5), C14(H14), C12(H12), C1(H1C), C13(H13), C4(H4), C3(H3),
  C6(H6)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 1.0054(2) 0.49671(18) 0.25179(8) 0.0418(4) Uani 1 1 d . . . . .
F1 F 0.9779(2) 0.28346(16) 0.28136(7) 0.0366(4) Uani 1 1 d . . . . .
F3 F 0.9921(2) 0.44985(17) 0.34685(8) 0.0406(4) Uani 1 1 d . . . . .
O1 O 0.6407(3) 0.38767(17) 0.22972(7) 0.0273(4) Uani 1 1 d . . . . .
H1 H 0.631807 0.300052 0.227763 0.041 Uiso 1 1 calc R U . . .
O2 O 0.4085(3) 0.29998(19) 0.32521(8) 0.0309(4) Uani 1 1 d . . . . .
N1 N 0.4226(3) 0.6037(2) 0.27845(12) 0.0288(5) Uani 1 1 d . . . . .
C8 C 0.6631(3) 0.6484(2) 0.35611(11) 0.0253(5) Uani 1 1 d . . . . .
H8 H 0.606061 0.604046 0.390355 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6311(3) 0.5842(2) 0.29523(11) 0.0236(5) Uani 1 1 d . . . . .
H9 H 0.711537 0.638719 0.265576 0.028 Uiso 1 1 calc R U . . .
C15 C 0.9177(3) 0.4146(3) 0.29266(12) 0.0293(5) Uani 1 1 d . . . . .
C10 C 0.6922(3) 0.4272(2) 0.28902(10) 0.0233(5) Uani 1 1 d . . . . .
C7 C 0.7667(4) 0.7637(3) 0.36483(11) 0.0291(5) Uani 1 1 d . . . . .
H7 H 0.836293 0.799088 0.330839 0.035 Uiso 1 1 calc R U . . .
C11 C 0.6019(3) 0.3315(2) 0.33562(11) 0.0252(5) Uani 1 1 d . . . . .
C5 C 0.8194(5) 1.0052(3) 0.52673(13) 0.0428(7) Uani 1 1 d . . . . .
H5 H 0.829508 1.061427 0.562081 0.051 Uiso 1 1 calc R U . . .
C2 C 0.7856(4) 0.8431(3) 0.42183(12) 0.0307(5) Uani 1 1 d . . . . .
C14 C 0.3555(4) 0.2028(3) 0.36817(12) 0.0366(6) Uani 1 1 d . . . . .
H14 H 0.229185 0.161118 0.371479 0.044 Uiso 1 1 calc R U . . .
C12 C 0.6673(4) 0.2591(3) 0.38387(12) 0.0386(6) Uani 1 1 d . . . . .
H12 H 0.795379 0.262970 0.400879 0.046 Uiso 1 1 calc R U . . .
C1 C 0.6533(4) 0.8261(3) 0.46960(12) 0.0349(6) Uani 1 1 d . . . . .
H1C H 0.550324 0.759302 0.466438 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5073(5) 0.1756(3) 0.40450(13) 0.0410(7) Uani 1 1 d . . . . .
H13 H 0.508549 0.112642 0.437778 0.049 Uiso 1 1 calc R U . . .
C4 C 0.9522(5) 1.0218(3) 0.47997(15) 0.0431(7) Uani 1 1 d . . . . .
H4 H 1.055284 1.088356 0.483482 0.052 Uiso 1 1 calc R U . . .
C3 C 0.9355(4) 0.9411(3) 0.42769(13) 0.0382(6) Uani 1 1 d . . . . .
H3 H 1.027397 0.953136 0.395739 0.046 Uiso 1 1 calc R U . . .
C6 C 0.6718(5) 0.9065(3) 0.52182(13) 0.0415(7) Uani 1 1 d . . . . .
H6 H 0.582323 0.893467 0.554339 0.050 Uiso 1 1 calc R U . . .
H1A H 0.405(6) 0.563(4) 0.2438(17) 0.045(10) Uiso 1 1 d . . . . .
H1B H 0.343(6) 0.569(4) 0.3070(17) 0.055(11) Uiso 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
F2 C15 1.337(3) . ?
F1 C15 1.341(3) . ?
F3 C15 1.342(3) . ?
O1 H1 0.8400 . ?
O1 C10 1.408(3) . ?
O2 C11 1.369(3) . ?
O2 C14 1.376(3) . ?
N1 C9 1.478(3) . ?
N1 H1A 0.86(4) . ?
N1 H1B 0.89(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.494(3) . ?
C8 C7 1.321(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.562(3) . ?
C15 C10 1.541(3) . ?
C10 C11 1.508(3) . ?
C7 H7 0.9500 . ?
C7 C2 1.476(3) . ?
C11 C12 1.346(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.382(5) . ?
C5 C6 1.382(5) . ?
C2 C1 1.397(4) . ?
C2 C3 1.390(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.334(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.424(4) . ?
C1 H1C 0.9500 . ?
C1 C6 1.392(4) . ?
C13 H13 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.393(4) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 H1 109.5 . . ?
C11 O2 C14 106.5(2) . . ?
C9 N1 H1A 107(3) . . ?
C9 N1 H1B 111(3) . . ?
H1A N1 H1B 112(3) . . ?
C9 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
C7 C8 C9 123.4(2) . . ?
N1 C9 C8 108.3(2) . . ?
N1 C9 H9 107.2 . . ?
N1 C9 C10 110.78(18) . . ?
C8 C9 H9 107.2 . . ?
C8 C9 C10 115.72(19) . . ?
C10 C9 H9 107.2 . . ?
F2 C15 F1 106.62(19) . . ?
F2 C15 F3 106.7(2) . . ?
F2 C15 C10 111.3(2) . . ?
F1 C15 F3 106.6(2) . . ?
F1 C15 C10 111.58(19) . . ?
F3 C15 C10 113.7(2) . . ?
O1 C10 C9 105.84(18) . . ?
O1 C10 C15 106.00(18) . . ?
O1 C10 C11 111.76(19) . . ?
C15 C10 C9 109.65(18) . . ?
C11 C10 C9 114.41(19) . . ?
C11 C10 C15 108.83(19) . . ?
C8 C7 H7 116.6 . . ?
C8 C7 C2 126.8(2) . . ?
C2 C7 H7 116.6 . . ?
O2 C11 C10 114.2(2) . . ?
C12 C11 O2 109.7(2) . . ?
C12 C11 C10 135.8(2) . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C1 C2 C7 121.9(2) . . ?
C3 C2 C7 119.3(2) . . ?
C3 C2 C1 118.8(2) . . ?
O2 C14 H14 125.0 . . ?
C13 C14 O2 110.0(2) . . ?
C13 C14 H14 125.0 . . ?
C11 C12 H12 126.6 . . ?
C11 C12 C13 106.7(2) . . ?
C13 C12 H12 126.6 . . ?
C2 C1 H1C 119.9 . . ?
C6 C1 C2 120.2(3) . . ?
C6 C1 H1C 119.9 . . ?
C14 C13 C12 106.9(2) . . ?
C14 C13 H13 126.5 . . ?
C12 C13 H13 126.5 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C3 C4 H4 119.9 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 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
F2 C15 C10 O1 59.1(2) . . . . ?
F2 C15 C10 C9 -54.7(3) . . . . ?
F2 C15 C10 C11 179.46(19) . . . . ?
F1 C15 C10 O1 -59.8(2) . . . . ?
F1 C15 C10 C9 -173.66(19) . . . . ?
F1 C15 C10 C11 60.5(3) . . . . ?
F3 C15 C10 O1 179.59(19) . . . . ?
F3 C15 C10 C9 65.8(3) . . . . ?
F3 C15 C10 C11 -60.1(3) . . . . ?
O1 C10 C11 O2 -44.2(3) . . . . ?
O1 C10 C11 C12 129.9(3) . . . . ?
O2 C11 C12 C13 0.9(3) . . . . ?
O2 C14 C13 C12 -0.2(3) . . . . ?
N1 C9 C10 O1 53.5(2) . . . . ?
N1 C9 C10 C15 167.4(2) . . . . ?
N1 C9 C10 C11 -70.0(3) . . . . ?
C8 C9 C10 O1 177.23(18) . . . . ?
C8 C9 C10 C15 -68.8(3) . . . . ?
C8 C9 C10 C11 53.7(3) . . . . ?
C8 C7 C2 C1 -17.6(4) . . . . ?
C8 C7 C2 C3 164.4(3) . . . . ?
C9 C8 C7 C2 172.0(2) . . . . ?
C9 C10 C11 O2 76.1(3) . . . . ?
C9 C10 C11 C12 -109.8(3) . . . . ?
C15 C10 C11 O2 -160.9(2) . . . . ?
C15 C10 C11 C12 13.2(4) . . . . ?
C10 C11 C12 C13 -173.4(3) . . . . ?
C7 C8 C9 N1 -110.0(3) . . . . ?
C7 C8 C9 C10 125.0(2) . . . . ?
C7 C2 C1 C6 -177.7(3) . . . . ?
C7 C2 C3 C4 177.4(3) . . . . ?
C11 O2 C14 C13 0.8(3) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C5 C4 C3 C2 0.0(4) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C14 O2 C11 C10 174.6(2) . . . . ?
C14 O2 C11 C12 -1.1(3) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C4 C5 C6 C1 -1.5(5) . . . . ?
C3 C2 C1 C6 0.3(4) . . . . ?
C6 C5 C4 C3 1.1(5) . . . . ?


_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_202418424_0m
_database_code_depnum_ccdc_archive 'CCDC 2392322'
loop_
_audit_author_name
_audit_author_address
'liang hanyu'
;shanghai normal university
China
;
_audit_update_record             
;
2024-10-19 deposited with the CCDC.	2025-01-03 downloaded from the CCDC.
;
_audit_creation_date             2024-10-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 Br F3 N O2, C4 H8 O'
_chemical_formula_sum            'C28 H27 Br F3 N O3'
_chemical_formula_weight         562.41
_chemical_absolute_configuration rmad
_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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8722(4)
_cell_length_b                   15.5610(10)
_cell_length_c                   28.0723(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2565.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7113
_cell_measurement_temperature    170
_cell_measurement_theta_max      63.185
_cell_measurement_theta_min      3.148
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.760
_exptl_absorpt_coefficient_mu    2.637
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0815 after correction.
The Ratio of minimum to maximum transmission is 0.7521.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            15090
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        63.595
_diffrn_reflns_theta_max         63.595
_diffrn_reflns_theta_min         3.148
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                3448
_reflns_number_total             4137
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 1156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.034(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.061
_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)+(0.0324P)²+0.0224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C12(H12), C2(H2A), C6(H6), C3(H3), C16(H16), C15(H15),
 C13(H13), C18(H18), C5(H5), C8(H8), C20(H20), C24(H24), C21(H21), C22(H22),
 C23(H23)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.55548(13) 0.94474(4) 0.53387(2) 0.0454(2) Uani 1 1 d . . . . .
F2 F 0.3375(7) 0.29286(18) 0.68128(10) 0.0442(9) Uani 1 1 d . . . . .
F3 F 0.2452(7) 0.23583(19) 0.61498(11) 0.0484(10) Uani 1 1 d . . . . .
F1 F 0.5970(7) 0.26288(19) 0.62961(11) 0.0476(9) Uani 1 1 d . . . . .
O2 O 0.1505(7) 0.4139(2) 0.63045(12) 0.0324(9) Uani 1 1 d . . . . .
H2 H 0.098720 0.451787 0.612091 0.049 Uiso 1 1 calc R U . . .
O1 O 0.9075(7) 0.5375(2) 0.58726(11) 0.0328(9) Uani 1 1 d . . . . .
O3 O 0.2376(8) 0.6510(2) 0.66240(14) 0.0424(10) Uani 1 1 d . . . . .
N1 N 0.5373(9) 0.5268(2) 0.61077(12) 0.0267(10) Uani 1 1 d . . . . .
H1 H 0.402847 0.551752 0.610742 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3597(10) 0.3756(3) 0.55814(17) 0.0257(13) Uani 1 1 d . . . . .
C10 C 0.3630(10) 0.3843(3) 0.61291(17) 0.0263(12) Uani 1 1 d . . . . .
C14 C 0.3416(11) 0.3545(3) 0.45924(19) 0.0334(14) Uani 1 1 d . . . . .
H14 H 0.335231 0.347116 0.425672 0.040 Uiso 1 1 calc R U . . .
C1 C 0.6702(10) 0.6596(3) 0.57699(16) 0.0260(12) Uani 1 1 d . . . . .
C17 C 0.3841(11) 0.2937(3) 0.63483(19) 0.0362(16) Uani 1 1 d . . . . .
C12 C 0.1633(9) 0.3451(3) 0.53586(19) 0.0294(12) Uani 1 1 d . . . . .
H12 H 0.032946 0.331673 0.554475 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8430(10) 0.7197(3) 0.58270(17) 0.0307(13) Uani 1 1 d . . . . .
H2A H 0.986738 0.702196 0.594840 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4621(11) 0.6841(3) 0.55722(16) 0.0287(13) Uani 1 1 d . . . . .
H6 H 0.345128 0.642713 0.552756 0.034 Uiso 1 1 calc R U . . .
C19 C 0.7956(11) 0.4483(4) 0.76082(18) 0.0343(13) Uani 1 1 d . . . . .
C9 C 0.5590(10) 0.4410(3) 0.63153(15) 0.0261(11) Uani 1 1 d . . . . .
H9 H 0.706115 0.415521 0.620479 0.031 Uiso 1 1 calc R U . . .
C7 C 0.7150(10) 0.5690(3) 0.59174(17) 0.0280(13) Uani 1 1 d . . . . .
C3 C 0.8069(11) 0.8049(3) 0.57079(17) 0.0316(14) Uani 1 1 d . . . . .
H3 H 0.922733 0.846585 0.575806 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5475(10) 0.3957(3) 0.53006(16) 0.0270(11) Uani 1 1 d . . . . .
H16 H 0.683066 0.416221 0.544609 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5383(11) 0.3860(3) 0.48071(17) 0.0332(13) Uani 1 1 d . . . . .
H15 H 0.666256 0.400922 0.461738 0.040 Uiso 1 1 calc R U . . .
C13 C 0.1562(11) 0.3341(3) 0.48711(18) 0.0328(14) Uani 1 1 d . . . . .
H13 H 0.021975 0.312299 0.472602 0.039 Uiso 1 1 calc R U . . .
C18 C 0.7524(10) 0.4323(3) 0.70988(16) 0.0307(13) Uani 1 1 d . . . . .
H18 H 0.872421 0.405316 0.692821 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4261(11) 0.7694(3) 0.54403(16) 0.0295(12) Uani 1 1 d . . . . .
H5 H 0.285905 0.786985 0.530237 0.035 Uiso 1 1 calc R U . . .
C8 C 0.5692(11) 0.4506(3) 0.68506(16) 0.0301(12) Uani 1 1 d . . . . .
H8 H 0.437875 0.470617 0.701394 0.036 Uiso 1 1 calc R U . . .
C20 C 1.0029(11) 0.4241(4) 0.78081(17) 0.0395(16) Uani 1 1 d . . . . .
H20 H 1.113033 0.396046 0.761533 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6011(11) 0.8282(3) 0.55162(17) 0.0320(14) Uani 1 1 d . . . . .
C24 C 0.6385(12) 0.4899(4) 0.79018(19) 0.0473(17) Uani 1 1 d . . . . .
H24 H 0.495442 0.507186 0.777601 0.057 Uiso 1 1 calc R U . . .
C21 C 1.0518(13) 0.4403(4) 0.82829(18) 0.0495(16) Uani 1 1 d . . . . .
H21 H 1.194095 0.422690 0.841099 0.059 Uiso 1 1 calc R U . . .
C22 C 0.8981(14) 0.4811(4) 0.8568(2) 0.054(2) Uani 1 1 d . . . . .
H22 H 0.933016 0.492170 0.889281 0.065 Uiso 1 1 calc R U . . .
C23 C 0.6901(14) 0.5062(4) 0.8380(2) 0.057(2) Uani 1 1 d . . . . .
H23 H 0.582123 0.534720 0.857607 0.068 Uiso 1 1 calc R U . . .
C28 C 0.3608(13) 0.7231(4) 0.6814(2) 0.057(2) Uani 1 1 d . . . . .
H28A H 0.288623 0.777869 0.671793 0.069 Uiso 1 1 calc R U . . .
H28B H 0.520662 0.722759 0.670218 0.069 Uiso 1 1 calc R U . . .
C25 C 0.0644(14) 0.6291(4) 0.6957(2) 0.0569(18) Uani 1 1 d . . . . .
H25A H 0.057976 0.566031 0.699951 0.068 Uiso 1 1 calc R U . . .
H25B H -0.085659 0.648971 0.683944 0.068 Uiso 1 1 calc R U . . .
C26 C 0.1190(18) 0.6717(5) 0.7420(2) 0.079(3) Uani 1 1 d . . . . .
H26A H 0.124857 0.629157 0.768184 0.094 Uiso 1 1 calc R U . . .
H26B H 0.004274 0.716100 0.749855 0.094 Uiso 1 1 calc R U . . .
C27 C 0.3501(17) 0.7118(5) 0.7339(3) 0.076(3) Uani 1 1 d . . . . .
H27A H 0.362604 0.767737 0.750442 0.091 Uiso 1 1 calc R U . . .
H27B H 0.473245 0.673404 0.745186 0.091 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.900(5) . ?
F2 C17 1.332(6) . ?
F3 C17 1.337(6) . ?
F1 C17 1.347(7) . ?
O2 H2 0.8400 . ?
O2 C10 1.418(6) . ?
O1 C7 1.239(6) . ?
O3 C28 1.438(7) . ?
O3 C25 1.422(8) . ?
N1 H1 0.8800 . ?
N1 C9 1.463(5) . ?
N1 C7 1.344(7) . ?
C11 C10 1.544(7) . ?
C11 C12 1.395(7) . ?
C11 C16 1.391(7) . ?
C10 C17 1.543(7) . ?
C10 C9 1.541(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(8) . ?
C14 C13 1.377(8) . ?
C1 C2 1.389(7) . ?
C1 C6 1.395(7) . ?
C1 C7 1.493(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(7) . ?
C2 H2A 0.9500 . ?
C2 C3 1.384(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.395(6) . ?
C19 C18 1.473(7) . ?
C19 C20 1.392(8) . ?
C19 C24 1.396(8) . ?
C9 H9 1.0000 . ?
C9 C8 1.511(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.372(8) . ?
C16 H16 0.9500 . ?
C16 C15 1.394(6) . ?
C15 H15 0.9500 . ?
C13 H13 0.9500 . ?
C18 H18 0.9500 . ?
C18 C8 1.313(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.392(8) . ?
C8 H8 0.9500 . ?
C20 H20 0.9500 . ?
C20 C21 1.386(7) . ?
C24 H24 0.9500 . ?
C24 C23 1.398(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.364(9) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(10) . ?
C23 H23 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C27 1.484(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.494(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.511(12) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 H2 109.5 . . ?
C25 O3 C28 107.6(5) . . ?
C9 N1 H1 118.7 . . ?
C7 N1 H1 118.7 . . ?
C7 N1 C9 122.5(5) . . ?
C12 C11 C10 119.1(5) . . ?
C16 C11 C10 122.3(5) . . ?
C16 C11 C12 118.5(5) . . ?
O2 C10 C11 111.3(4) . . ?
O2 C10 C17 103.2(4) . . ?
O2 C10 C9 110.7(4) . . ?
C17 C10 C11 108.5(4) . . ?
C9 C10 C11 113.4(4) . . ?
C9 C10 C17 109.1(4) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(5) . . ?
C2 C1 C6 120.2(5) . . ?
C2 C1 C7 118.4(5) . . ?
C6 C1 C7 121.5(5) . . ?
F2 C17 F3 106.0(5) . . ?
F2 C17 F1 107.1(5) . . ?
F2 C17 C10 112.5(4) . . ?
F3 C17 F1 106.3(4) . . ?
F3 C17 C10 113.6(5) . . ?
F1 C17 C10 110.9(5) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.3(6) . . ?
C3 C2 H2A 119.8 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.9(5) . . ?
C5 C6 H6 120.1 . . ?
C20 C19 C18 119.8(5) . . ?
C20 C19 C24 117.7(5) . . ?
C24 C19 C18 122.5(5) . . ?
N1 C9 C10 108.8(4) . . ?
N1 C9 H9 108.2 . . ?
N1 C9 C8 108.0(4) . . ?
C10 C9 H9 108.2 . . ?
C8 C9 C10 115.1(4) . . ?
C8 C9 H9 108.2 . . ?
O1 C7 N1 123.7(5) . . ?
O1 C7 C1 120.4(5) . . ?
N1 C7 C1 115.8(5) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3 120.6 . . ?
C11 C16 H16 119.7 . . ?
C11 C16 C15 120.5(5) . . ?
C15 C16 H16 119.7 . . ?
C14 C15 C16 120.0(6) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C13 C12 120.7(5) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C19 C18 H18 115.9 . . ?
C8 C18 C19 128.3(5) . . ?
C8 C18 H18 115.9 . . ?
C6 C5 H5 120.9 . . ?
C4 C5 C6 118.2(6) . . ?
C4 C5 H5 120.9 . . ?
C9 C8 H8 118.7 . . ?
C18 C8 C9 122.6(5) . . ?
C18 C8 H8 118.7 . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.3(6) . . ?
C21 C20 H20 119.3 . . ?
C3 C4 Br1 118.6(4) . . ?
C3 C4 C5 122.5(5) . . ?
C5 C4 Br1 118.9(4) . . ?
C19 C24 H24 119.8 . . ?
C19 C24 C23 120.5(7) . . ?
C23 C24 H24 119.8 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.8(6) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.3(6) . . ?
C23 C22 H22 120.3 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.4(7) . . ?
C22 C23 H23 119.8 . . ?
O3 C28 H28A 110.8 . . ?
O3 C28 H28B 110.8 . . ?
O3 C28 C27 104.8(6) . . ?
H28A C28 H28B 108.9 . . ?
C27 C28 H28A 110.8 . . ?
C27 C28 H28B 110.8 . . ?
O3 C25 H25A 110.1 . . ?
O3 C25 H25B 110.1 . . ?
O3 C25 C26 108.2(6) . . ?
H25A C25 H25B 108.4 . . ?
C26 C25 H25A 110.1 . . ?
C26 C25 H25B 110.1 . . ?
C25 C26 H26A 110.9 . . ?
C25 C26 H26B 110.9 . . ?
C25 C26 C27 104.2(6) . . ?
H26A C26 H26B 108.9 . . ?
C27 C26 H26A 110.9 . . ?
C27 C26 H26B 110.9 . . ?
C28 C27 C26 103.7(6) . . ?
C28 C27 H27A 111.0 . . ?
C28 C27 H27B 111.0 . . ?
C26 C27 H27A 111.0 . . ?
C26 C27 H27B 111.0 . . ?
H27A C27 H27B 109.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C10 C17 F2 -47.7(6) . . . . ?
O2 C10 C17 F3 72.7(6) . . . . ?
O2 C10 C17 F1 -167.6(4) . . . . ?
O2 C10 C9 N1 -66.8(5) . . . . ?
O2 C10 C9 C8 54.5(6) . . . . ?
O3 C28 C27 C26 -34.1(7) . . . . ?
O3 C25 C26 C27 -5.8(8) . . . . ?
N1 C9 C8 C18 -113.0(6) . . . . ?
C11 C10 C17 F2 -165.9(5) . . . . ?
C11 C10 C17 F3 -45.5(7) . . . . ?
C11 C10 C17 F1 74.2(6) . . . . ?
C11 C10 C9 N1 59.1(5) . . . . ?
C11 C10 C9 C8 -179.5(4) . . . . ?
C11 C12 C13 C14 -1.1(7) . . . . ?
C11 C16 C15 C14 -1.2(7) . . . . ?
C10 C11 C12 C13 -178.2(4) . . . . ?
C10 C11 C16 C15 179.3(4) . . . . ?
C10 C9 C8 C18 125.2(6) . . . . ?
C1 C2 C3 C4 -2.5(8) . . . . ?
C1 C6 C5 C4 -0.6(7) . . . . ?
C17 C10 C9 N1 -179.8(4) . . . . ?
C17 C10 C9 C8 -58.4(6) . . . . ?
C12 C11 C10 O2 -38.4(6) . . . . ?
C12 C11 C10 C17 74.6(6) . . . . ?
C12 C11 C10 C9 -164.0(4) . . . . ?
C12 C11 C16 C15 0.4(7) . . . . ?
C2 C1 C6 C5 -1.2(7) . . . . ?
C2 C1 C7 O1 -34.0(7) . . . . ?
C2 C1 C7 N1 144.3(5) . . . . ?
C2 C3 C4 Br1 -178.4(4) . . . . ?
C2 C3 C4 C5 0.5(8) . . . . ?
C6 C1 C2 C3 2.8(7) . . . . ?
C6 C1 C7 O1 145.1(5) . . . . ?
C6 C1 C7 N1 -36.6(6) . . . . ?
C6 C5 C4 Br1 180.0(3) . . . . ?
C6 C5 C4 C3 1.0(8) . . . . ?
C19 C18 C8 C9 171.9(5) . . . . ?
C19 C20 C21 C22 -0.5(9) . . . . ?
C19 C24 C23 C22 -0.2(10) . . . . ?
C9 N1 C7 O1 4.8(7) . . . . ?
C9 N1 C7 C1 -173.4(4) . . . . ?
C9 C10 C17 F2 70.0(6) . . . . ?
C9 C10 C17 F3 -169.5(5) . . . . ?
C9 C10 C17 F1 -49.9(6) . . . . ?
C7 N1 C9 C10 -133.7(5) . . . . ?
C7 N1 C9 C8 100.8(5) . . . . ?
C7 C1 C2 C3 -178.1(5) . . . . ?
C7 C1 C6 C5 179.7(4) . . . . ?
C16 C11 C10 O2 142.7(5) . . . . ?
C16 C11 C10 C17 -104.3(5) . . . . ?
C16 C11 C10 C9 17.1(6) . . . . ?
C16 C11 C12 C13 0.8(7) . . . . ?
C15 C14 C13 C12 0.4(8) . . . . ?
C13 C14 C15 C16 0.8(7) . . . . ?
C18 C19 C20 C21 178.2(5) . . . . ?
C18 C19 C24 C23 -177.8(6) . . . . ?
C20 C19 C18 C8 -179.9(6) . . . . ?
C20 C19 C24 C23 0.0(9) . . . . ?
C20 C21 C22 C23 0.3(10) . . . . ?
C24 C19 C18 C8 -2.1(9) . . . . ?
C24 C19 C20 C21 0.4(9) . . . . ?
C21 C22 C23 C24 0.0(10) . . . . ?
C28 O3 C25 C26 -15.8(8) . . . . ?
C25 O3 C28 C27 31.4(7) . . . . ?
C25 C26 C27 C28 24.2(8) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
