# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2100007'
loop_
_audit_author_name
_audit_author_address
'Wang Huan'
;Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2024-01-15 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         ?
_chemical_formula_sum            'C24 H17 Br N P'
_chemical_formula_weight         430.26

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'
N N 0.0061 0.0033 '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           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                   10.659(2)
_cell_length_b                   8.1881(16)
_cell_length_c                   11.525(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.380(3)
_cell_angle_gamma                90
_cell_volume                     986.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1846
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      23.61

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   0.5795
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.173
_shelx_estimated_absorpt_T_min   0.562
_shelx_estimated_absorpt_T_max   0.670
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            4998
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.802
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        24.992
_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 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3353
_reflns_number_gt                2712
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_max     0.926
_reflns_Friedel_fraction_full    0.926

_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 APEX II'
_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    SHELXTL
_computing_publication_material  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)+(0.0010P)²+0.0009P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 996 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.038(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3353
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_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 0.07905(5) 0.24010(12) 0.68559(7) 0.0934(3) Uani 1 1 d . . . . .
C1 C 0.6938(5) 0.6217(6) 0.6794(4) 0.0490(12) Uani 1 1 d . . . . .
C2 C 0.6731(6) 0.7265(8) 0.7691(5) 0.0687(15) Uani 1 1 d . . . . .
H2 H 0.5998 0.7145 0.8008 0.082 Uiso 1 1 calc R U . . .
C3 C 0.7605(8) 0.8488(8) 0.8116(6) 0.083(2) Uani 1 1 d . . . . .
H3 H 0.7469 0.9157 0.8731 0.099 Uiso 1 1 calc R U . . .
C4 C 0.8655(8) 0.8706(9) 0.7637(6) 0.082(2) Uani 1 1 d . . . . .
H4 H 0.9238 0.9525 0.7926 0.098 Uiso 1 1 calc R U . . .
C5 C 0.8859(6) 0.7745(8) 0.6747(6) 0.0744(18) Uani 1 1 d . . . . .
H5 H 0.9574 0.7921 0.6413 0.089 Uiso 1 1 calc R U . . .
C6 C 0.8016(5) 0.6493(6) 0.6318(5) 0.0583(14) Uani 1 1 d . . . . .
H6 H 0.8176 0.5834 0.5706 0.070 Uiso 1 1 calc R U . . .
C7 C 0.7311(5) 0.2101(7) 0.5629(4) 0.0552(13) Uani 1 1 d . . . . .
H7 H 0.7442 0.1712 0.6402 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7903(6) 0.1338(8) 0.4819(5) 0.0667(16) Uani 1 1 d . . . . .
H8 H 0.8440 0.0452 0.5050 0.080 Uiso 1 1 calc R U . . .
C9 C 0.7705(6) 0.1880(8) 0.3674(6) 0.0714(19) Uani 1 1 d . . . . .
H9 H 0.8115 0.1365 0.3133 0.086 Uiso 1 1 calc R U . . .
C10 C 0.6918(9) 0.3158(8) 0.3322(5) 0.085(2) Uani 1 1 d . . . . .
H10 H 0.6795 0.3524 0.2543 0.102 Uiso 1 1 calc R U . . .
C11 C 0.6288(7) 0.3933(7) 0.4132(5) 0.0721(18) Uani 1 1 d . . . . .
H11 H 0.5713 0.4773 0.3876 0.086 Uiso 1 1 calc R U . . .
C12 C 0.6516(5) 0.3454(6) 0.5308(4) 0.0506(13) Uani 1 1 d . . . . .
C13 C 0.6856(5) 0.3044(6) 0.8475(4) 0.0486(13) Uani 1 1 d . . . . .
C14 C 0.8146(5) 0.3363(7) 0.8610(5) 0.0597(14) Uani 1 1 d . . . . .
H14 H 0.8465 0.3955 0.8044 0.072 Uiso 1 1 calc R U . . .
C15 C 0.8961(6) 0.2770(8) 0.9625(5) 0.0700(17) Uani 1 1 d . . . . .
H15 H 0.9833 0.2986 0.9745 0.084 Uiso 1 1 calc R U . . .
C16 C 0.8481(7) 0.1866(8) 1.0450(5) 0.0739(19) Uani 1 1 d . . . . .
H16 H 0.9041 0.1452 1.1106 0.089 Uiso 1 1 calc R U . . .
C17 C 0.7199(6) 0.1568(7) 1.0323(5) 0.0646(16) Uani 1 1 d . . . . .
H17 H 0.6889 0.0976 1.0896 0.078 Uiso 1 1 calc R U . . .
C18 C 0.6362(5) 0.2156(7) 0.9332(4) 0.0512(12) Uani 1 1 d . . . . .
C19 C 0.4994(5) 0.2028(6) 0.8925(4) 0.0509(12) Uani 1 1 d . . . . .
C20 C 0.4005(7) 0.1308(7) 0.9383(5) 0.0656(16) Uani 1 1 d . . . . .
H20 H 0.4189 0.0738 1.0094 0.079 Uiso 1 1 calc R U . . .
C21 C 0.2760(7) 0.1446(7) 0.8780(6) 0.0691(17) Uani 1 1 d . . . . .
H21 H 0.2093 0.0994 0.9086 0.083 Uiso 1 1 calc R U . . .
C22 C 0.2515(5) 0.2277(8) 0.7699(5) 0.0617(14) Uani 1 1 d . . . . .
C23 C 0.3456(5) 0.2972(6) 0.7208(5) 0.0528(13) Uani 1 1 d . . . . .
H23 H 0.3268 0.3503 0.6481 0.063 Uiso 1 1 calc R U . . .
C24 C 0.4693(5) 0.2853(6) 0.7837(4) 0.0482(12) Uani 1 1 d . . . . .
N1 N 0.5822(4) 0.3494(5) 0.7550(4) 0.0477(10) Uani 1 1 d . . . . .
P1 P 0.57297(12) 0.46647(16) 0.62736(12) 0.0491(3) 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 C22 1.904(5) . ?
C1 C6 1.387(8) . ?
C1 C2 1.395(8) . ?
C1 P1 1.824(5) . ?
C2 C3 1.389(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.345(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(8) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.376(8) . ?
C7 C12 1.400(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.352(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(7) . ?
C11 H11 0.9300 . ?
C12 P1 1.814(6) . ?
C13 C14 1.377(8) . ?
C13 C18 1.410(7) . ?
C13 N1 1.422(6) . ?
C14 C15 1.400(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(9) . ?
C16 H16 0.9300 . ?
C17 C18 1.390(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.444(7) . ?
C19 C20 1.400(8) . ?
C19 C24 1.404(7) . ?
C20 C21 1.376(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.399(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(7) . ?
C23 C24 1.377(7) . ?
C23 H23 0.9300 . ?
C24 N1 1.411(6) . ?
N1 P1 1.743(4) . ?

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
C6 C1 C2 117.2(5) . . ?
C6 C1 P1 124.8(4) . . ?
C2 C1 P1 117.9(5) . . ?
C3 C2 C1 120.8(6) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.1(6) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.4(7) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.8(7) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 120.6(6) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C12 121.0(5) . . ?
C8 C7 H7 119.5 . . ?
C12 C7 H7 119.5 . . ?
C9 C8 C7 120.2(6) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.6(6) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.0(6) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.5(6) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 117.5(5) . . ?
C11 C12 P1 115.6(5) . . ?
C7 C12 P1 126.8(4) . . ?
C14 C13 C18 121.4(5) . . ?
C14 C13 N1 130.1(5) . . ?
C18 C13 N1 108.5(4) . . ?
C13 C14 C15 118.0(6) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C16 C15 C14 120.6(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 121.4(5) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 119.5(6) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 119.1(5) . . ?
C17 C18 C19 133.2(5) . . ?
C13 C18 C19 107.6(4) . . ?
C20 C19 C24 118.9(5) . . ?
C20 C19 C18 134.1(5) . . ?
C24 C19 C18 107.1(4) . . ?
C21 C20 C19 119.9(5) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 118.8(5) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C23 C22 C21 123.2(5) . . ?
C23 C22 Br1 118.7(5) . . ?
C21 C22 Br1 118.2(4) . . ?
C22 C23 C24 117.2(5) . . ?
C22 C23 H23 121.4 . . ?
C24 C23 H23 121.4 . . ?
C23 C24 C19 122.0(5) . . ?
C23 C24 N1 128.5(5) . . ?
C19 C24 N1 109.4(4) . . ?
C24 N1 C13 107.4(4) . . ?
C24 N1 P1 119.6(3) . . ?
C13 N1 P1 133.0(4) . . ?
N1 P1 C12 105.1(2) . . ?
N1 P1 C1 100.8(2) . . ?
C12 P1 C1 101.6(2) . . ?

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
C6 C1 C2 C3 -2.7(8) . . . . ?
P1 C1 C2 C3 -179.2(5) . . . . ?
C1 C2 C3 C4 2.0(10) . . . . ?
C2 C3 C4 C5 0.1(11) . . . . ?
C3 C4 C5 C6 -1.3(10) . . . . ?
C2 C1 C6 C5 1.4(8) . . . . ?
P1 C1 C6 C5 177.6(4) . . . . ?
C4 C5 C6 C1 0.6(9) . . . . ?
C12 C7 C8 C9 -1.0(9) . . . . ?
C7 C8 C9 C10 -0.6(9) . . . . ?
C8 C9 C10 C11 -0.5(10) . . . . ?
C9 C10 C11 C12 3.4(10) . . . . ?
C10 C11 C12 C7 -4.9(9) . . . . ?
C10 C11 C12 P1 175.4(5) . . . . ?
C8 C7 C12 C11 3.8(8) . . . . ?
C8 C7 C12 P1 -176.6(4) . . . . ?
C18 C13 C14 C15 0.4(8) . . . . ?
N1 C13 C14 C15 179.7(5) . . . . ?
C13 C14 C15 C16 1.2(8) . . . . ?
C14 C15 C16 C17 -2.1(9) . . . . ?
C15 C16 C17 C18 1.4(9) . . . . ?
C16 C17 C18 C13 0.2(8) . . . . ?
C16 C17 C18 C19 178.4(6) . . . . ?
C14 C13 C18 C17 -1.1(7) . . . . ?
N1 C13 C18 C17 179.4(4) . . . . ?
C14 C13 C18 C19 -179.7(5) . . . . ?
N1 C13 C18 C19 0.9(5) . . . . ?
C17 C18 C19 C20 1.9(10) . . . . ?
C13 C18 C19 C20 -179.9(6) . . . . ?
C17 C18 C19 C24 -178.8(6) . . . . ?
C13 C18 C19 C24 -0.5(5) . . . . ?
C24 C19 C20 C21 -1.3(8) . . . . ?
C18 C19 C20 C21 178.0(6) . . . . ?
C19 C20 C21 C22 1.5(9) . . . . ?
C20 C21 C22 C23 -0.3(9) . . . . ?
C20 C21 C22 Br1 178.3(5) . . . . ?
C21 C22 C23 C24 -1.1(8) . . . . ?
Br1 C22 C23 C24 -179.7(4) . . . . ?
C22 C23 C24 C19 1.3(7) . . . . ?
C22 C23 C24 N1 -178.1(5) . . . . ?
C20 C19 C24 C23 -0.1(8) . . . . ?
C18 C19 C24 C23 -179.6(5) . . . . ?
C20 C19 C24 N1 179.4(4) . . . . ?
C18 C19 C24 N1 -0.1(5) . . . . ?
C23 C24 N1 C13 -179.9(5) . . . . ?
C19 C24 N1 C13 0.6(5) . . . . ?
C23 C24 N1 P1 2.4(7) . . . . ?
C19 C24 N1 P1 -177.1(3) . . . . ?
C14 C13 N1 C24 179.7(5) . . . . ?
C18 C13 N1 C24 -0.9(5) . . . . ?
C14 C13 N1 P1 -3.1(8) . . . . ?
C18 C13 N1 P1 176.3(4) . . . . ?
C24 N1 P1 C12 -113.2(4) . . . . ?
C13 N1 P1 C12 69.8(5) . . . . ?
C24 N1 P1 C1 141.6(4) . . . . ?
C13 N1 P1 C1 -35.4(5) . . . . ?
C11 C12 P1 N1 164.4(4) . . . . ?
C7 C12 P1 N1 -15.2(5) . . . . ?
C11 C12 P1 C1 -90.9(5) . . . . ?
C7 C12 P1 C1 89.5(5) . . . . ?
C6 C1 P1 N1 120.0(4) . . . . ?
C2 C1 P1 N1 -63.8(5) . . . . ?
C6 C1 P1 C12 11.9(5) . . . . ?
C2 C1 P1 C12 -171.9(4) . . . . ?

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.041



