# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_T
_database_code_depnum_ccdc_archive 'CCDC 2106103'
loop_
_audit_author_name
_audit_author_address
'xiaoyu xie'
;Nanjing Agricultural University
China
;
_audit_update_record             
;
2021-08-28 deposited with the CCDC.	2022-01-31 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         'C36 H26 Br O2 P'
_chemical_formula_sum            'C36 H26 Br O2 P'
_chemical_formula_weight         601.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   19.891(4)
_cell_length_b                   9.6242(19)
_cell_length_c                   29.836(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.97(3)
_cell_angle_gamma                90
_cell_volume                     5681(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    65371
_cell_measurement_theta_min      2.670
_cell_measurement_theta_max      27.440

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             2464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.536
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65371
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.670
_diffrn_reflns_theta_max         27.440
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6418
_reflns_number_gt                5007
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0491P)²+4.6989P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         6418
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.04260(2) 0.43635(2) 0.11056(2) 0.05038(10) Uani 1 1 d . . . . .
P1 P -0.13969(3) 0.62241(6) 0.12278(2) 0.03210(14) Uani 1 1 d . . . . .
O1 O -0.10525(9) 0.67327(19) 0.16643(5) 0.0437(4) Uani 1 1 d . . . . .
O2 O -0.08354(8) 0.91371(16) 0.09151(6) 0.0391(4) Uani 1 1 d . . . . .
C1 C -0.16578(12) 0.4424(2) 0.12712(8) 0.0348(5) Uani 1 1 d . . . . .
C2 C -0.13221(13) 0.3634(3) 0.16168(8) 0.0437(6) Uani 1 1 d . . . . .
H2A H -0.0984 0.4041 0.1813 0.052 Uiso 1 1 calc R U . . .
C3 C -0.14869(14) 0.2243(3) 0.16720(10) 0.0516(7) Uani 1 1 d . . . . .
H3A H -0.1263 0.1731 0.1906 0.062 Uiso 1 1 calc R U . . .
C4 C -0.19801(14) 0.1622(3) 0.13805(10) 0.0520(7) Uani 1 1 d . . . . .
H4A H -0.2082 0.0686 0.1413 0.062 Uiso 1 1 calc R U . . .
C5 C -0.23224(13) 0.2393(3) 0.10401(10) 0.0502(7) Uani 1 1 d . . . . .
H5A H -0.2658 0.1975 0.0845 0.060 Uiso 1 1 calc R U . . .
C6 C -0.21709(13) 0.3790(3) 0.09855(9) 0.0442(6) Uani 1 1 d . . . . .
H6A H -0.2411 0.4305 0.0759 0.053 Uiso 1 1 calc R U . . .
C7 C -0.21604(11) 0.7192(2) 0.10455(8) 0.0371(5) Uani 1 1 d . . . . .
C8 C -0.22766(14) 0.7922(3) 0.06441(10) 0.0560(7) Uani 1 1 d . . . . .
H8A H -0.1969 0.7864 0.0431 0.067 Uiso 1 1 calc R U . . .
C9 C -0.28537(17) 0.8744(4) 0.05591(12) 0.0708(9) Uani 1 1 d . . . . .
H9A H -0.2929 0.9229 0.0289 0.085 Uiso 1 1 calc R U . . .
C10 C -0.33089(15) 0.8840(4) 0.08711(15) 0.0736(11) Uani 1 1 d . . . . .
H10A H -0.3692 0.9392 0.0813 0.088 Uiso 1 1 calc R U . . .
C11 C -0.32008(16) 0.8125(4) 0.12683(15) 0.0748(10) Uani 1 1 d . . . . .
H11A H -0.3511 0.8193 0.1480 0.090 Uiso 1 1 calc R U . . .
C12 C -0.26284(15) 0.7295(3) 0.13570(11) 0.0585(8) Uani 1 1 d . . . . .
H12A H -0.2560 0.6807 0.1627 0.070 Uiso 1 1 calc R U . . .
C13 C 0.02156(11) 0.7428(2) 0.04930(7) 0.0307(5) Uani 1 1 d . . . . .
C14 C -0.01306(13) 0.8038(3) 0.01118(8) 0.0407(6) Uani 1 1 d . . . . .
H14A H -0.0592 0.8207 0.0105 0.049 Uiso 1 1 calc R U . . .
C15 C 0.02015(14) 0.8396(3) -0.02565(9) 0.0490(6) Uani 1 1 d . . . . .
H15A H -0.0041 0.8787 -0.0509 0.059 Uiso 1 1 calc R U . . .
C16 C 0.08840(14) 0.8181(3) -0.02537(9) 0.0491(6) Uani 1 1 d . . . . .
H16A H 0.1106 0.8424 -0.0502 0.059 Uiso 1 1 calc R U . . .
C17 C 0.12340(13) 0.7604(3) 0.01208(9) 0.0496(6) Uani 1 1 d . . . . .
H17A H 0.1697 0.7459 0.0126 0.060 Uiso 1 1 calc R U . . .
C18 C 0.09062(12) 0.7227(3) 0.04952(8) 0.0405(6) Uani 1 1 d . . . . .
H18A H 0.1152 0.6841 0.0747 0.049 Uiso 1 1 calc R U . . .
C19 C 0.10635(11) 0.5919(2) 0.19631(7) 0.0312(5) Uani 1 1 d . . . . .
C20 C 0.07674(14) 0.5031(3) 0.22509(8) 0.0421(6) Uani 1 1 d . . . . .
H20A H 0.0299 0.4986 0.2239 0.051 Uiso 1 1 calc R U . . .
C21 C 0.1162(2) 0.4206(3) 0.25575(9) 0.0626(9) Uani 1 1 d . . . . .
H21A H 0.0958 0.3606 0.2747 0.075 Uiso 1 1 calc R U . . .
C22 C 0.1851(2) 0.4282(3) 0.25789(11) 0.0745(11) Uani 1 1 d . . . . .
H22A H 0.2117 0.3727 0.2782 0.089 Uiso 1 1 calc R U . . .
C23 C 0.21538(17) 0.5174(4) 0.23017(11) 0.0714(10) Uani 1 1 d . . . . .
H23A H 0.2623 0.5226 0.2320 0.086 Uiso 1 1 calc R U . . .
C24 C 0.17625(13) 0.5999(3) 0.19928(9) 0.0507(7) Uani 1 1 d . . . . .
H24A H 0.1970 0.6604 0.1807 0.061 Uiso 1 1 calc R U . . .
C25 C 0.01033(11) 0.9138(2) 0.14681(7) 0.0291(4) Uani 1 1 d . . . . .
C26 C 0.00322(12) 1.0556(2) 0.15660(8) 0.0358(5) Uani 1 1 d . . . . .
H26A H -0.0266 1.1104 0.1381 0.043 Uiso 1 1 calc R U . . .
C27 C 0.04036(13) 1.1139(3) 0.19353(8) 0.0427(6) Uani 1 1 d . . . . .
H27A H 0.0359 1.2079 0.1998 0.051 Uiso 1 1 calc R U . . .
C28 C 0.08422(13) 1.0317(3) 0.22109(8) 0.0435(6) Uani 1 1 d . . . . .
H28A H 0.1088 1.0707 0.2462 0.052 Uiso 1 1 calc R U . . .
C29 C 0.09203(12) 0.8915(3) 0.21164(8) 0.0395(5) Uani 1 1 d . . . . .
H29A H 0.1217 0.8379 0.2306 0.047 Uiso 1 1 calc R U . . .
C30 C 0.05574(11) 0.8297(2) 0.17392(7) 0.0294(4) Uani 1 1 d . . . . .
C31 C -0.08287(11) 0.6280(2) 0.07845(7) 0.0302(5) Uani 1 1 d . . . . .
C32 C -0.09773(14) 0.5583(3) 0.04058(9) 0.0477(6) Uani 1 1 d . . . . .
H32A H -0.0669 0.5548 0.0192 0.057 Uiso 1 1 calc R U . . .
H32B H -0.1390 0.5126 0.0353 0.057 Uiso 1 1 calc R U . . .
C33 C -0.03458(11) 0.8525(2) 0.10930(7) 0.0283(4) Uani 1 1 d . . . . .
C34 C -0.01607(10) 0.7077(2) 0.09093(7) 0.0282(4) Uani 1 1 d . . . . .
C35 C 0.02973(11) 0.6277(2) 0.12586(7) 0.0297(4) Uani 1 1 d . . . . .
C36 C 0.06272(10) 0.6798(2) 0.16339(7) 0.0288(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
Br1 C35 1.921(2) . ?
P1 O1 1.4897(17) . ?
P1 C1 1.817(2) . ?
P1 C7 1.816(2) . ?
P1 C31 1.828(2) . ?
O2 C33 1.212(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.400(3) . ?
C2 C3 1.392(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C12 1.386(4) . ?
C7 C8 1.387(4) . ?
C8 C9 1.395(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.368(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.368(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.393(5) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C18 1.386(3) . ?
C13 C14 1.396(3) . ?
C13 C34 1.553(3) . ?
C14 C15 1.383(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.372(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.398(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.386(3) . ?
C19 C24 1.386(3) . ?
C19 C36 1.502(3) . ?
C20 C21 1.390(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.369(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.373(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.392(4) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 C30 1.405(3) . ?
C25 C26 1.406(3) . ?
C25 C33 1.480(3) . ?
C26 C27 1.380(3) . ?
C26 H26A 0.9300 . ?
C27 C28 1.383(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.391(3) . ?
C28 H28A 0.9300 . ?
C29 C30 1.404(3) . ?
C29 H29A 0.9300 . ?
C30 C36 1.486(3) . ?
C31 C32 1.321(3) . ?
C31 C34 1.546(3) . ?
C32 H32A 0.9300 . ?
C32 H32B 0.9300 . ?
C33 C34 1.556(3) . ?
C34 C35 1.520(3) . ?
C35 C36 1.335(3) . ?

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 C1 111.09(11) . . ?
O1 P1 C7 112.79(11) . . ?
C1 P1 C7 105.93(11) . . ?
O1 P1 C31 111.11(10) . . ?
C1 P1 C31 106.40(10) . . ?
C7 P1 C31 109.21(11) . . ?
C2 C1 C6 118.4(2) . . ?
C2 C1 P1 117.02(18) . . ?
C6 C1 P1 124.58(19) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
C12 C7 C8 118.7(2) . . ?
C12 C7 P1 115.8(2) . . ?
C8 C7 P1 125.27(19) . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C7 C12 C11 120.4(3) . . ?
C7 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C18 C13 C14 117.8(2) . . ?
C18 C13 C34 121.70(19) . . ?
C14 C13 C34 120.34(19) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C15 C16 C17 118.9(2) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C16 C17 C18 121.1(2) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
C13 C18 C17 120.3(2) . . ?
C13 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C20 C19 C24 118.9(2) . . ?
C20 C19 C36 119.9(2) . . ?
C24 C19 C36 121.2(2) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C22 C21 C20 119.6(3) . . ?
C22 C21 H21A 120.2 . . ?
C20 C21 H21A 120.2 . . ?
C21 C22 C23 120.3(3) . . ?
C21 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23A 119.8 . . ?
C24 C23 H23A 119.8 . . ?
C19 C24 C23 119.9(3) . . ?
C19 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C30 C25 C26 120.8(2) . . ?
C30 C25 C33 120.50(19) . . ?
C26 C25 C33 118.5(2) . . ?
C27 C26 C25 120.2(2) . . ?
C27 C26 H26A 119.9 . . ?
C25 C26 H26A 119.9 . . ?
C26 C27 C28 119.6(2) . . ?
C26 C27 H27A 120.2 . . ?
C28 C27 H27A 120.2 . . ?
C27 C28 C29 120.7(2) . . ?
C27 C28 H28A 119.6 . . ?
C29 C28 H28A 119.6 . . ?
C28 C29 C30 121.0(2) . . ?
C28 C29 H29A 119.5 . . ?
C30 C29 H29A 119.5 . . ?
C25 C30 C29 117.6(2) . . ?
C25 C30 C36 120.41(19) . . ?
C29 C30 C36 121.9(2) . . ?
C32 C31 C34 124.6(2) . . ?
C32 C31 P1 120.24(18) . . ?
C34 C31 P1 114.90(14) . . ?
C31 C32 H32A 120.0 . . ?
C31 C32 H32B 120.0 . . ?
H32A C32 H32B 120.0 . . ?
O2 C33 C25 122.14(19) . . ?
O2 C33 C34 119.32(19) . . ?
C25 C33 C34 118.47(18) . . ?
C35 C34 C31 110.64(17) . . ?
C35 C34 C13 110.75(17) . . ?
C31 C34 C13 112.89(17) . . ?
C35 C34 C33 111.05(17) . . ?
C31 C34 C33 107.48(17) . . ?
C13 C34 C33 103.80(16) . . ?
C36 C35 C34 126.32(19) . . ?
C36 C35 Br1 119.53(16) . . ?
C34 C35 Br1 114.07(14) . . ?
C35 C36 C30 119.53(19) . . ?
C35 C36 C19 122.51(19) . . ?
C30 C36 C19 117.96(18) . . ?

_refine_diff_density_max         0.389
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.053



