# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
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data_20210830T37_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2106628'
loop_
_audit_author_name
_audit_author_address
'Mei-Mei Li'
;Chengdu university of traditional chinese medcine
China
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 Br F3 N2 O3'
_chemical_formula_weight         559.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.3667(3)
_cell_length_b                   7.8133(2)
_cell_length_c                   14.3984(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.3130(10)
_cell_angle_gamma                90
_cell_volume                     1233.34(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      68.18

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.756
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21753
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.182
_diffrn_reflns_theta_max         68.262
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4471
_reflns_number_gt                4208
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_max     0.977
_reflns_Friedel_fraction_full    0.981

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1804 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4471
_refine_ls_number_parameters     334
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1131
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
Br01 Br 0.32619(4) 0.71258(10) 1.15712(3) 0.0772(2) Uani 1 1 d . . . . .
H1 H 0.613(9) 0.648(13) 0.369(7) 0.12(4) Uiso 1 1 d . . . . .
C1 C 0.1830(3) 0.6872(4) 0.6400(2) 0.0385(7) Uani 1 1 d . . . . .
O002 O 0.3977(3) 0.3574(4) 0.7336(2) 0.0586(7) Uani 1 1 d . . . . .
H2 H 0.605(8) 0.584(12) 0.465(7) 0.11(3) Uiso 1 1 d . . . . .
O003 O 0.5776(3) 0.6713(5) 0.5834(2) 0.0623(8) Uani 1 1 d . . . . .
F004 F 0.2652(4) 0.5440(5) 0.3408(2) 0.0860(10) Uani 1 1 d . . . . .
F005 F 0.1888(3) 0.7226(6) 0.4189(2) 0.0940(11) Uani 1 1 d . . . . .
F006 F 0.3699(4) 0.7611(5) 0.4048(3) 0.0920(11) Uani 1 1 d . . . . .
N007 N 0.1938(3) 0.4197(4) 0.7094(2) 0.0442(6) Uani 1 1 d . . . . .
N008 N 0.3820(3) 0.6376(4) 0.5951(2) 0.0425(6) Uani 1 1 d . . . . .
C00A C 0.1159(3) 0.5571(5) 0.6687(3) 0.0410(7) Uani 1 1 d . . . . .
C00C C 0.3113(3) 0.4536(5) 0.7092(3) 0.0424(7) Uani 1 1 d . . . . .
C00D C 0.3162(3) 0.6383(5) 0.6698(3) 0.0388(7) Uani 1 1 d . . . . .
C00E C 0.1259(4) 0.8335(5) 0.5978(3) 0.0489(8) Uani 1 1 d . . . . .
H00E H 0.169989 0.921419 0.579320 0.059 Uiso 1 1 calc R U . . .
C00F C 0.2649(4) 0.8114(6) 0.9602(3) 0.0530(9) Uani 1 1 d . . . . .
H00F H 0.197515 0.863512 0.973453 0.064 Uiso 1 1 calc R U . . .
C00G C 0.3487(3) 0.7236(6) 1.0312(3) 0.0502(8) Uani 1 1 d . . . . .
C00H C -0.0089(4) 0.5693(6) 0.6562(3) 0.0527(9) Uani 1 1 d . . . . .
H00H H -0.052734 0.482488 0.676006 0.063 Uiso 1 1 calc R U . . .
C00I C 0.3820(3) 0.7417(5) 0.8471(2) 0.0403(7) Uani 1 1 d . . . . .
C00J C 0.1517(4) 0.2530(5) 0.7343(3) 0.0528(9) Uani 1 1 d . . . . .
H00A H 0.210862 0.166619 0.729036 0.063 Uiso 1 1 calc R U . . .
H00B H 0.075308 0.225179 0.687863 0.063 Uiso 1 1 calc R U . . .
C00K C 0.2830(4) 0.8202(5) 0.8698(3) 0.0498(9) Uani 1 1 d . . . . .
H00K H 0.227356 0.880515 0.822073 0.060 Uiso 1 1 calc R U . . .
C00L C 0.2918(4) 0.6437(6) 0.4186(3) 0.0546(9) Uani 1 1 d . . . . .
C00M C 0.3967(3) 0.7601(4) 0.7463(3) 0.0416(7) Uani 1 1 d . . . . .
H00M H 0.372396 0.877261 0.725424 0.050 Uiso 1 1 calc R U . . .
C00N C 0.5019(3) 0.6817(5) 0.6294(3) 0.0479(8) Uani 1 1 d . . . . .
C00O C 0.3423(4) 0.5391(5) 0.5074(3) 0.0466(8) Uani 1 1 d . . . . .
H00C H 0.280270 0.458723 0.514539 0.056 Uiso 1 1 calc R U . . .
H00D H 0.410928 0.473234 0.498673 0.056 Uiso 1 1 calc R U . . .
C00P C -0.0653(4) 0.7166(8) 0.6128(3) 0.0633(10) Uani 1 1 d . . . . .
H00P H -0.149057 0.728704 0.603123 0.076 Uiso 1 1 calc R U . . .
C00Q C 0.4627(3) 0.6522(6) 0.9201(3) 0.0512(9) Uani 1 1 d . . . . .
H00Q H 0.528702 0.596321 0.906868 0.061 Uiso 1 1 calc R U . . .
C00R C -0.0003(4) 0.8464(7) 0.5835(4) 0.0596(10) Uani 1 1 d . . . . .
H00R H -0.041103 0.943334 0.553957 0.072 Uiso 1 1 calc R U . . .
C00S C 0.1329(4) 0.2452(5) 0.8344(3) 0.0474(8) Uani 1 1 d . . . . .
C00T C 0.4472(4) 0.6443(6) 1.0120(3) 0.0581(10) Uani 1 1 d . . . . .
H00T H 0.503110 0.585714 1.060390 0.070 Uiso 1 1 calc R U . . .
C00U C 0.5247(3) 0.7336(6) 0.7330(3) 0.0532(9) Uani 1 1 d . . . . .
H00G H 0.571872 0.838533 0.745769 0.064 Uiso 1 1 calc R U . . .
H00I H 0.567889 0.644480 0.775458 0.064 Uiso 1 1 calc R U . . .
C00V C 0.2192(4) 0.3088(6) 0.9143(3) 0.0595(10) Uani 1 1 d . . . . .
H00V H 0.287496 0.365666 0.905798 0.071 Uiso 1 1 calc R U . . .
C00W C 0.2051(5) 0.2889(6) 1.0057(4) 0.0616(10) Uani 1 1 d . . . . .
H00W H 0.264672 0.331093 1.058026 0.074 Uiso 1 1 calc R U . . .
C00X C 0.1040(4) 0.2073(7) 1.0211(3) 0.0611(10) Uani 1 1 d . . . . .
C00Y C 0.0312(4) 0.1677(6) 0.8493(4) 0.0589(11) Uani 1 1 d . . . . .
H00Y H -0.029213 0.128033 0.796778 0.071 Uiso 1 1 calc R U . . .
C00Z C 0.0170(4) 0.1472(7) 0.9423(4) 0.0666(12) Uani 1 1 d . . . . .
H00Z H -0.051946 0.092296 0.950865 0.080 Uiso 1 1 calc R U . . .
C010 C 0.0917(7) 0.1810(10) 1.1218(4) 0.0913(19) Uani 1 1 d . . . . .
H01A H 0.012941 0.133315 1.118883 0.137 Uiso 1 1 calc R U . . .
H01B H 0.100212 0.288875 1.154771 0.137 Uiso 1 1 calc R U . . .
H01C H 0.154049 0.103944 1.155825 0.137 Uiso 1 1 calc R U . . .
O1B O 0.6298(6) 0.5838(7) 0.4065(4) 0.1027(18) 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
Br01 C00G 1.898(4) . ?
C1 C00E 1.374(5) . ?
C1 C00A 1.397(5) . ?
C1 C00D 1.510(4) . ?
O002 C00C 1.213(5) . ?
O003 C00N 1.219(5) . ?
F004 C00L 1.332(5) . ?
F005 C00L 1.324(6) . ?
F006 C00L 1.327(6) . ?
N007 C00C 1.362(5) . ?
N007 C00A 1.416(5) . ?
N007 C00J 1.465(5) . ?
N008 C00N 1.366(5) . ?
N008 C00O 1.446(5) . ?
N008 C00D 1.463(4) . ?
C00A C00H 1.385(5) . ?
C00C C00D 1.557(5) . ?
C00D C00M 1.557(5) . ?
C00E C00R 1.398(6) . ?
C00E H00E 0.9300 . ?
C00F C00K 1.373(6) . ?
C00F C00G 1.382(6) . ?
C00F H00F 0.9300 . ?
C00G C00T 1.370(6) . ?
C00H C00P 1.383(8) . ?
C00H H00H 0.9300 . ?
C00I C00Q 1.388(5) . ?
C00I C00K 1.394(6) . ?
C00I C00M 1.511(5) . ?
C00J C00S 1.513(6) . ?
C00J H00A 0.9700 . ?
C00J H00B 0.9700 . ?
C00K H00K 0.9300 . ?
C00L C00O 1.498(6) . ?
C00M C00U 1.530(5) . ?
C00M H00M 0.9800 . ?
C00N C00U 1.502(5) . ?
C00O H00C 0.9700 . ?
C00O H00D 0.9700 . ?
C00P C00R 1.385(8) . ?
C00P H00P 0.9300 . ?
C00Q C00T 1.382(6) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S C00Y 1.371(6) . ?
C00S C00V 1.392(6) . ?
C00T H00T 0.9300 . ?
C00U H00G 0.9700 . ?
C00U H00I 0.9700 . ?
C00V C00W 1.375(7) . ?
C00V H00V 0.9300 . ?
C00W C00X 1.383(7) . ?
C00W H00W 0.9300 . ?
C00X C00Z 1.376(8) . ?
C00X C010 1.507(7) . ?
C00Y C00Z 1.399(7) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C010 H01A 0.9600 . ?
C010 H01B 0.9600 . ?
C010 H01C 0.9600 . ?
O1B H1 0.72(10) . ?
O1B H2 0.96(9) . ?

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
C00E C1 C00A 120.3(3) . . ?
C00E C1 C00D 131.1(3) . . ?
C00A C1 C00D 108.4(3) . . ?
C00C N007 C00A 111.0(3) . . ?
C00C N007 C00J 123.9(3) . . ?
C00A N007 C00J 124.5(3) . . ?
C00N N008 C00O 120.1(3) . . ?
C00N N008 C00D 112.9(3) . . ?
C00O N008 C00D 122.8(3) . . ?
C00H C00A C1 122.1(4) . . ?
C00H C00A N007 127.8(4) . . ?
C1 C00A N007 110.1(3) . . ?
O002 C00C N007 126.8(4) . . ?
O002 C00C C00D 125.1(3) . . ?
N007 C00C C00D 108.1(3) . . ?
N008 C00D C1 117.5(3) . . ?
N008 C00D C00M 101.7(3) . . ?
C1 C00D C00M 113.8(3) . . ?
N008 C00D C00C 109.8(3) . . ?
C1 C00D C00C 102.0(3) . . ?
C00M C00D C00C 112.3(3) . . ?
C1 C00E C00R 118.1(4) . . ?
C1 C00E H00E 120.9 . . ?
C00R C00E H00E 120.9 . . ?
C00K C00F C00G 118.7(4) . . ?
C00K C00F H00F 120.7 . . ?
C00G C00F H00F 120.7 . . ?
C00T C00G C00F 121.0(4) . . ?
C00T C00G Br01 119.7(3) . . ?
C00F C00G Br01 119.2(3) . . ?
C00P C00H C00A 116.9(4) . . ?
C00P C00H H00H 121.5 . . ?
C00A C00H H00H 121.5 . . ?
C00Q C00I C00K 117.2(3) . . ?
C00Q C00I C00M 123.8(3) . . ?
C00K C00I C00M 119.0(3) . . ?
N007 C00J C00S 114.0(3) . . ?
N007 C00J H00A 108.8 . . ?
C00S C00J H00A 108.8 . . ?
N007 C00J H00B 108.8 . . ?
C00S C00J H00B 108.8 . . ?
H00A C00J H00B 107.7 . . ?
C00F C00K C00I 122.2(4) . . ?
C00F C00K H00K 118.9 . . ?
C00I C00K H00K 118.9 . . ?
F005 C00L F006 107.8(4) . . ?
F005 C00L F004 105.7(4) . . ?
F006 C00L F004 106.9(4) . . ?
F005 C00L C00O 113.0(3) . . ?
F006 C00L C00O 112.6(4) . . ?
F004 C00L C00O 110.4(4) . . ?
C00I C00M C00U 117.2(3) . . ?
C00I C00M C00D 115.3(3) . . ?
C00U C00M C00D 103.3(3) . . ?
C00I C00M H00M 106.8 . . ?
C00U C00M H00M 106.8 . . ?
C00D C00M H00M 106.8 . . ?
O003 C00N N008 124.6(4) . . ?
O003 C00N C00U 126.6(4) . . ?
N008 C00N C00U 108.7(3) . . ?
N008 C00O C00L 114.6(3) . . ?
N008 C00O H00C 108.6 . . ?
C00L C00O H00C 108.6 . . ?
N008 C00O H00D 108.6 . . ?
C00L C00O H00D 108.6 . . ?
H00C C00O H00D 107.6 . . ?
C00H C00P C00R 121.8(4) . . ?
C00H C00P H00P 119.1 . . ?
C00R C00P H00P 119.1 . . ?
C00T C00Q C00I 121.5(4) . . ?
C00T C00Q H00Q 119.3 . . ?
C00I C00Q H00Q 119.3 . . ?
C00P C00R C00E 120.7(4) . . ?
C00P C00R H00R 119.6 . . ?
C00E C00R H00R 119.6 . . ?
C00Y C00S C00V 117.9(4) . . ?
C00Y C00S C00J 120.2(4) . . ?
C00V C00S C00J 121.8(4) . . ?
C00G C00T C00Q 119.4(4) . . ?
C00G C00T H00T 120.3 . . ?
C00Q C00T H00T 120.3 . . ?
C00N C00U C00M 103.9(3) . . ?
C00N C00U H00G 111.0 . . ?
C00M C00U H00G 111.0 . . ?
C00N C00U H00I 111.0 . . ?
C00M C00U H00I 111.0 . . ?
H00G C00U H00I 109.0 . . ?
C00W C00V C00S 121.0(4) . . ?
C00W C00V H00V 119.5 . . ?
C00S C00V H00V 119.5 . . ?
C00X C00W C00V 121.1(4) . . ?
C00X C00W H00W 119.4 . . ?
C00V C00W H00W 119.4 . . ?
C00Z C00X C00W 118.2(4) . . ?
C00Z C00X C010 121.2(5) . . ?
C00W C00X C010 120.6(5) . . ?
C00S C00Y C00Z 121.0(4) . . ?
C00S C00Y H00Y 119.5 . . ?
C00Z C00Y H00Y 119.5 . . ?
C00X C00Z C00Y 120.7(4) . . ?
C00X C00Z H00Z 119.6 . . ?
C00Y C00Z H00Z 119.6 . . ?
C00X C010 H01A 109.5 . . ?
C00X C010 H01B 109.5 . . ?
H01A C010 H01B 109.5 . . ?
C00X C010 H01C 109.5 . . ?
H01A C010 H01C 109.5 . . ?
H01B C010 H01C 109.5 . . ?
H1 O1B H2 125(10) . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.044



