# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_ChenC-69
_database_code_depnum_ccdc_archive 'CCDC 2336234'
loop_
_audit_author_name
_audit_author_address
'Ruji Wang'
;Deptarment of  Chemistry, Tsinghua University,
China
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H20 O3 P S, C F3 O3 S'
_chemical_formula_sum            'C18 H20 F3 O6 P S2'
_chemical_formula_weight         484.43

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'
O O 0.0492 0.0322 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3092(2)
_cell_length_b                   10.0133(2)
_cell_length_c                   18.3326(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.7760(10)
_cell_angle_gamma                90
_cell_volume                     2075.84(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    13311
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      66.4

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.617
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.064
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            16158
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.622
_diffrn_reflns_theta_max         66.555
_diffrn_reflns_theta_full        66.555
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             3536
_reflns_number_gt                3476
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0983P)²+3.4060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3536
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1643
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_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
S1 S 0.10736(6) -0.00005(6) 0.13675(3) 0.0229(2) Uani 1 1 d . . . . .
S2 S 0.62833(9) 0.63470(10) 0.16870(5) 0.0491(3) Uani 1 1 d . . . . .
P1 P 0.29739(6) 0.20403(7) 0.19818(4) 0.0220(2) Uani 1 1 d . . . . .
F1 F 0.5570(3) 0.4096(3) 0.2226(2) 0.0854(9) Uani 1 1 d . . . . .
F2 F 0.7149(4) 0.3944(4) 0.1653(3) 0.140(2) Uani 1 1 d . . . . .
F3 F 0.7129(4) 0.4812(5) 0.2698(2) 0.1307(17) Uani 1 1 d . . . . .
O1 O 0.3091(2) 0.2895(2) 0.26271(12) 0.0348(5) Uani 1 1 d . . . . .
O2 O 0.26454(17) 0.2722(2) 0.12451(11) 0.0290(5) Uani 1 1 d . . . . .
O3 O 0.40960(18) 0.1188(2) 0.18078(11) 0.0308(5) Uani 1 1 d . . . . .
O4 O 0.5623(7) 0.6087(5) 0.1055(3) 0.155(3) Uani 1 1 d . . . . .
O5 O 0.5645(4) 0.7013(4) 0.2235(2) 0.0934(14) Uani 1 1 d . . . . .
O6 O 0.7422(4) 0.6861(4) 0.1571(3) 0.1186(19) Uani 1 1 d . . . . .
C1 C 0.0487(2) 0.1253(3) 0.07807(15) 0.0243(6) Uani 1 1 d . . . . .
C2 C -0.0479(3) 0.2053(3) 0.09371(17) 0.0300(6) Uani 1 1 d . . . . .
H2 H -0.0881 0.1982 0.1387 0.036 Uiso 1 1 calc R U . . .
C3 C -0.0827(3) 0.2960(3) 0.04057(18) 0.0361(7) Uani 1 1 d . . . . .
H3 H -0.1473 0.3541 0.0494 0.043 Uiso 1 1 calc R U . . .
C4 C -0.0242(3) 0.3029(3) -0.02557(18) 0.0373(7) Uani 1 1 d . . . . .
H4 H -0.0500 0.3655 -0.0613 0.045 Uiso 1 1 calc R U . . .
C5 C 0.0717(3) 0.2200(3) -0.04052(16) 0.0307(7) Uani 1 1 d . . . . .
H5 H 0.1107 0.2254 -0.0860 0.037 Uiso 1 1 calc R U . . .
C6 C 0.1089(2) 0.1296(3) 0.01226(15) 0.0247(6) Uani 1 1 d . . . . .
C7 C 0.2080(2) 0.0352(3) 0.01025(15) 0.0250(6) Uani 1 1 d . . . . .
C8 C 0.2210(2) -0.0399(3) 0.07386(14) 0.0238(6) Uani 1 1 d . . . . .
C9 C 0.3065(3) -0.1368(3) 0.08432(16) 0.0291(6) Uani 1 1 d . . . . .
H9 H 0.3118 -0.1867 0.1283 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3843(3) -0.1577(3) 0.02755(18) 0.0354(7) Uani 1 1 d . . . . .
H10 H 0.4447 -0.2232 0.0324 0.042 Uiso 1 1 calc R U . . .
C11 C 0.3745(3) -0.0833(3) -0.03645(17) 0.0360(7) Uani 1 1 d . . . . .
H11 H 0.4290 -0.0988 -0.0745 0.043 Uiso 1 1 calc R U . . .
C12 C 0.2877(3) 0.0123(3) -0.04608(16) 0.0311(7) Uani 1 1 d . . . . .
H12 H 0.2821 0.0616 -0.0902 0.037 Uiso 1 1 calc R U . . .
C13 C 0.1745(2) 0.0923(3) 0.21191(14) 0.0238(6) Uani 1 1 d . . . . .
H13A H 0.1109 0.1454 0.2345 0.029 Uiso 1 1 calc R U . . .
H13B H 0.2005 0.0257 0.2487 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3483(3) 0.3429(4) 0.0777(2) 0.0394(8) Uani 1 1 d . . . . .
H14A H 0.3655 0.2880 0.0342 0.047 Uiso 1 1 calc R U . . .
H14B H 0.4234 0.3583 0.1047 0.047 Uiso 1 1 calc R U . . .
C15 C 0.2968(5) 0.4715(4) 0.0549(3) 0.0634(12) Uani 1 1 d . . . . .
H15A H 0.2185 0.4564 0.0328 0.095 Uiso 1 1 calc R U . . .
H15B H 0.3483 0.5141 0.0191 0.095 Uiso 1 1 calc R U . . .
H15C H 0.2892 0.5298 0.0975 0.095 Uiso 1 1 calc R U . . .
C16 C 0.5015(3) 0.0918(5) 0.2369(2) 0.0532(10) Uani 1 1 d . . . . .
H16A H 0.5752 0.0640 0.2127 0.064 Uiso 1 1 calc R U . . .
H16B H 0.5184 0.1751 0.2642 0.064 Uiso 1 1 calc R U . . .
C17 C 0.4661(5) -0.0128(4) 0.2885(2) 0.0604(11) Uani 1 1 d . . . . .
H17A H 0.3944 0.0153 0.3137 0.091 Uiso 1 1 calc R U . . .
H17B H 0.5299 -0.0274 0.3243 0.091 Uiso 1 1 calc R U . . .
H17C H 0.4504 -0.0959 0.2619 0.091 Uiso 1 1 calc R U . . .
C18 C 0.6550(3) 0.4715(5) 0.2055(2) 0.0524(10) 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
S1 C1 1.776(3) . ?
S1 C8 1.784(3) . ?
S1 C13 1.817(3) . ?
S2 O4 1.394(5) . ?
S2 O6 1.406(4) . ?
S2 O5 1.412(3) . ?
S2 C18 1.792(4) . ?
P1 O1 1.465(2) . ?
P1 O2 1.554(2) . ?
P1 O3 1.566(2) . ?
P1 C13 1.804(3) . ?
F1 C18 1.311(5) . ?
F2 C18 1.270(5) . ?
F3 C18 1.343(5) . ?
O2 C14 1.469(4) . ?
O3 C16 1.478(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.394(4) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.467(4) . ?
C7 C8 1.394(4) . ?
C7 C12 1.398(4) . ?
C8 C9 1.381(4) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.472(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.470(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C8 91.90(13) . . ?
C1 S1 C13 104.40(13) . . ?
C8 S1 C13 107.84(13) . . ?
O4 S2 O6 115.1(4) . . ?
O4 S2 O5 114.0(4) . . ?
O6 S2 O5 114.4(3) . . ?
O4 S2 C18 103.2(3) . . ?
O6 S2 C18 104.0(2) . . ?
O5 S2 C18 104.3(2) . . ?
O1 P1 O2 117.61(13) . . ?
O1 P1 O3 114.72(13) . . ?
O2 P1 O3 104.32(11) . . ?
O1 P1 C13 108.13(13) . . ?
O2 P1 C13 102.60(12) . . ?
O3 P1 C13 108.55(13) . . ?
C14 O2 P1 124.85(19) . . ?
C16 O3 P1 121.5(2) . . ?
C2 C1 C6 123.8(3) . . ?
C2 C1 S1 124.9(2) . . ?
C6 C1 S1 111.3(2) . . ?
C3 C2 C1 116.8(3) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 118.5(3) . . ?
C5 C6 C7 128.9(3) . . ?
C1 C6 C7 112.6(2) . . ?
C8 C7 C12 117.9(3) . . ?
C8 C7 C6 113.5(2) . . ?
C12 C7 C6 128.6(3) . . ?
C9 C8 C7 124.1(3) . . ?
C9 C8 S1 125.2(2) . . ?
C7 C8 S1 110.6(2) . . ?
C8 C9 C10 116.9(3) . . ?
C8 C9 H9 121.6 . . ?
C10 C9 H9 121.6 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C7 118.9(3) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?
P1 C13 S1 121.63(15) . . ?
P1 C13 H13A 106.9 . . ?
S1 C13 H13A 106.9 . . ?
P1 C13 H13B 106.9 . . ?
S1 C13 H13B 106.9 . . ?
H13A C13 H13B 106.7 . . ?
O2 C14 C15 109.4(3) . . ?
O2 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
O2 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 O3 112.5(3) . . ?
C17 C16 H16A 109.1 . . ?
O3 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
O3 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F2 C18 F1 108.1(4) . . ?
F2 C18 F3 107.2(5) . . ?
F1 C18 F3 103.2(4) . . ?
F2 C18 S2 115.1(3) . . ?
F1 C18 S2 112.5(3) . . ?
F3 C18 S2 110.0(4) . . ?

_refine_diff_density_max         0.658
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.084



####################################################################### 
# 
# 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_ChenC-73R
_database_code_depnum_ccdc_archive 'CCDC 2338655'
loop_
_audit_author_name
_audit_author_address
'Ruji Wang'
;Deptarment of  Chemistry, Tsinghua University,
China
;
_audit_update_record             
;
2024-03-08 deposited with the CCDC.	2024-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 Br N O3 P'
_chemical_formula_sum            'C20 H23 Br N O3 P'
_chemical_formula_weight         436.27

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'
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'
P P 0.2955 0.4335 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.23480(10)
_cell_length_b                   10.7943(2)
_cell_length_c                   11.6518(2)
_cell_angle_alpha                108.8050(10)
_cell_angle_beta                 95.4870(10)
_cell_angle_gamma                113.088(2)
_cell_volume                     978.00(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14895
_cell_measurement_theta_min      4.1
_cell_measurement_theta_max      73.8

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    3.799
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.571
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro 1.171.43.90a (Rigaku OD, 2023)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            17978
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.145
_diffrn_reflns_theta_max         73.802
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3776
_reflns_number_gt                3696
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.43.90a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.90a (Rigaku OD, 2023)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0499P)²+0.8846P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3776
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_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
Br1 Br -0.06235(3) 0.03115(2) 0.20883(2) 0.02766(10) Uani 1 1 d . . . . .
P1 P 0.86751(7) 0.46121(6) 0.25932(5) 0.02057(13) Uani 1 1 d . . . . .
O1 O 0.72984(19) 0.43877(18) 0.16717(14) 0.0263(3) Uani 1 1 d . . . . .
O2 O 1.00922(19) 0.44041(18) 0.20145(14) 0.0262(3) Uani 1 1 d . . . . .
O3 O 0.96259(19) 0.61879(16) 0.36789(14) 0.0236(3) Uani 1 1 d . . . . .
N1 N 0.5211(2) 0.37227(19) 0.53589(16) 0.0199(4) Uani 1 1 d . . . . .
C1 C 0.6771(3) 0.4042(2) 0.5226(2) 0.0207(4) Uani 1 1 d . . . . .
H1 H 0.7731 0.4623 0.5894 0.025 Uiso 1 1 calc R U . . .
C2 C 0.6736(3) 0.3403(2) 0.3992(2) 0.0207(4) Uani 1 1 d . . . . .
C3 C 0.5056(3) 0.2631(2) 0.3315(2) 0.0197(4) Uani 1 1 d . . . . .
C4 C 0.4243(3) 0.1785(2) 0.2042(2) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.4842 0.1666 0.1430 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2565(3) 0.1129(2) 0.1691(2) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.1999 0.0542 0.0835 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1694(3) 0.1333(2) 0.2604(2) 0.0234(4) Uani 1 1 d . . . . .
C7 C 0.2437(3) 0.2194(2) 0.3862(2) 0.0206(4) Uani 1 1 d . . . . .
H7 H 0.1828 0.2341 0.4461 0.025 Uiso 1 1 calc R U . . .
C8 C 0.4138(3) 0.2834(2) 0.41995(19) 0.0199(4) Uani 1 1 d . . . . .
C9 C 0.8162(3) 0.3451(2) 0.3452(2) 0.0221(4) Uani 1 1 d . . . . .
H9A H 0.7912 0.2444 0.2887 0.027 Uiso 1 1 calc R U . . .
H9B H 0.9120 0.3801 0.4143 0.027 Uiso 1 1 calc R U . . .
C10 C 0.9703(3) 0.3381(3) 0.0720(2) 0.0305(5) Uani 1 1 d . . . . .
H10A H 0.9036 0.3581 0.0154 0.037 Uiso 1 1 calc R U . . .
H10B H 0.9080 0.2361 0.0644 0.037 Uiso 1 1 calc R U . . .
C11 C 1.1285(3) 0.3587(3) 0.0378(2) 0.0357(6) Uani 1 1 d . . . . .
H11A H 1.1868 0.4586 0.0422 0.054 Uiso 1 1 calc R U . . .
H11B H 1.1066 0.2885 -0.0476 0.054 Uiso 1 1 calc R U . . .
H11C H 1.1951 0.3423 0.0964 0.054 Uiso 1 1 calc R U . . .
C12 C 1.0314(3) 0.7454(3) 0.3331(2) 0.0318(5) Uani 1 1 d . . . . .
H12A H 0.9429 0.7614 0.2956 0.038 Uiso 1 1 calc R U . . .
H12B H 1.0941 0.7275 0.2707 0.038 Uiso 1 1 calc R U . . .
C13 C 1.1403(3) 0.8770(3) 0.4487(2) 0.0329(5) Uani 1 1 d . . . . .
H13A H 1.0754 0.8998 0.5065 0.049 Uiso 1 1 calc R U . . .
H13B H 1.1955 0.9606 0.4261 0.049 Uiso 1 1 calc R U . . .
H13C H 1.2217 0.8570 0.4894 0.049 Uiso 1 1 calc R U . . .
C14 C 0.4793(3) 0.4100(2) 0.65550(19) 0.0226(4) Uani 1 1 d . . . . .
H14A H 0.3704 0.4071 0.6412 0.027 Uiso 1 1 calc R U . . .
H14B H 0.5586 0.5116 0.7111 0.027 Uiso 1 1 calc R U . . .
C15 C 0.4776(3) 0.3092(2) 0.72182(19) 0.0202(4) Uani 1 1 d . . . . .
C16 C 0.4440(3) 0.3388(2) 0.8391(2) 0.0220(4) Uani 1 1 d . . . . .
H16 H 0.4166 0.4169 0.8732 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4505(3) 0.2549(3) 0.9063(2) 0.0262(5) Uani 1 1 d . . . . .
H17 H 0.4290 0.2763 0.9867 0.031 Uiso 1 1 calc R U . . .
C18 C 0.4884(3) 0.1394(3) 0.8557(2) 0.0285(5) Uani 1 1 d . . . . .
H18 H 0.4939 0.0825 0.9019 0.034 Uiso 1 1 calc R U . . .
C19 C 0.5183(3) 0.1074(3) 0.7380(2) 0.0306(5) Uani 1 1 d . . . . .
H19 H 0.5426 0.0275 0.7030 0.037 Uiso 1 1 calc R U . . .
C20 C 0.5127(3) 0.1918(2) 0.6709(2) 0.0257(5) Uani 1 1 d . . . . .
H20 H 0.5330 0.1693 0.5901 0.031 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 C6 1.906(2) . ?
P1 O1 1.4688(16) . ?
P1 O3 1.5792(16) . ?
P1 O2 1.5872(16) . ?
P1 C9 1.798(2) . ?
O2 C10 1.461(3) . ?
O3 C12 1.470(3) . ?
N1 C8 1.375(3) . ?
N1 C1 1.380(3) . ?
N1 C14 1.455(3) . ?
C1 C2 1.370(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.433(3) . ?
C2 C9 1.503(3) . ?
C3 C4 1.405(3) . ?
C3 C8 1.413(3) . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(3) . ?
C7 C8 1.399(3) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.502(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.493(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.520(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C20 1.393(3) . ?
C15 C16 1.393(3) . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 H20 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
O1 P1 O3 116.19(9) . . ?
O1 P1 O2 114.07(9) . . ?
O3 P1 O2 102.02(9) . . ?
O1 P1 C9 115.13(10) . . ?
O3 P1 C9 102.18(9) . . ?
O2 P1 C9 105.60(9) . . ?
C10 O2 P1 119.62(15) . . ?
C12 O3 P1 118.22(13) . . ?
C8 N1 C1 108.40(17) . . ?
C8 N1 C14 126.39(19) . . ?
C1 N1 C14 124.67(18) . . ?
C2 C1 N1 110.30(19) . . ?
C2 C1 H1 124.9 . . ?
N1 C1 H1 124.9 . . ?
C1 C2 C3 106.33(19) . . ?
C1 C2 C9 127.3(2) . . ?
C3 C2 C9 126.37(19) . . ?
C4 C3 C8 119.2(2) . . ?
C4 C3 C2 133.6(2) . . ?
C8 C3 C2 107.13(18) . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 123.2(2) . . ?
C7 C6 Br1 118.46(17) . . ?
C5 C6 Br1 118.25(16) . . ?
C6 C7 C8 115.99(19) . . ?
C6 C7 H7 122.0 . . ?
C8 C7 H7 122.0 . . ?
N1 C8 C7 129.72(19) . . ?
N1 C8 C3 107.81(19) . . ?
C7 C8 C3 122.47(19) . . ?
C2 C9 P1 113.73(14) . . ?
C2 C9 H9A 108.8 . . ?
P1 C9 H9A 108.8 . . ?
C2 C9 H9B 108.8 . . ?
P1 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O2 C10 C11 107.5(2) . . ?
O2 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 C13 108.34(18) . . ?
O3 C12 H12A 110.0 . . ?
C13 C12 H12A 110.0 . . ?
O3 C12 H12B 110.0 . . ?
C13 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 113.91(17) . . ?
N1 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N1 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C20 C15 C16 119.38(19) . . ?
C20 C15 C14 122.19(19) . . ?
C16 C15 C14 118.41(19) . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.8(2) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.1(2) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?

_refine_diff_density_max         0.544
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.078



