# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_L
_database_code_depnum_ccdc_archive 'CCDC 2014442'
loop_
_audit_author_name
_audit_author_address
'Wenyan Hao'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2020-07-06 deposited with the CCDC.	2020-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 Br N O P S'
_chemical_formula_weight         516.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
S S 0.1246 0.1234 '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                   8.7427(6)
_cell_length_b                   11.4201(7)
_cell_length_c                   12.4832(9)
_cell_angle_alpha                82.935(6)
_cell_angle_beta                 73.455(7)
_cell_angle_gamma                75.613(6)
_cell_volume                     1155.45(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4041
_cell_measurement_theta_min      3.9280
_cell_measurement_theta_max      26.5710

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.959
_shelx_estimated_absorpt_T_min   0.695
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_T_min  0.42805
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12088
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.373
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4705
_reflns_number_gt                3481
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0619P)²+0.2270P] 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         4705
_refine_ls_number_parameters     326
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_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 0.12311(4) -0.05726(3) 0.61510(3) 0.05963(17) Uani 1 1 d . . . . .
S1 S 0.58901(14) 0.20791(8) 0.15850(7) 0.0601(3) Uani 1 1 d . . . . .
P1 P 0.65095(10) 0.44611(7) 0.18162(7) 0.0393(2) Uani 1 1 d . . . . .
O1 O 0.7061(3) 0.4341(2) 0.05942(18) 0.0521(6) Uani 1 1 d . . . . .
C1 C 0.5615(4) 0.3182(3) 0.2516(3) 0.0394(7) Uani 1 1 d . . . . .
N1 N 0.4882(3) 0.3195(2) 0.3557(2) 0.0423(6) Uani 1 1 d . . . . .
C2 C 0.4083(4) 0.2268(3) 0.4099(3) 0.0386(7) Uani 1 1 d . . . . .
C3 C 0.3060(4) 0.2504(3) 0.5167(3) 0.0471(8) Uani 1 1 d . . . . .
H3 H 0.296289 0.323060 0.547199 0.056 Uiso 1 1 calc R U . . .
C4 C 0.2188(4) 0.1679(3) 0.5780(3) 0.0486(8) Uani 1 1 d . . . . .
H4 H 0.150113 0.184364 0.649070 0.058 Uiso 1 1 calc R U . . .
C5 C 0.2356(4) 0.0613(3) 0.5318(3) 0.0426(8) Uani 1 1 d . . . . .
C6 C 0.3352(4) 0.0354(3) 0.4267(3) 0.0451(8) Uani 1 1 d . . . . .
H6 H 0.343148 -0.037725 0.397615 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4251(4) 0.1177(3) 0.3625(3) 0.0389(7) Uani 1 1 d . . . . .
C8 C 0.5353(4) 0.0858(3) 0.2511(3) 0.0442(8) Uani 1 1 d . . . . .
C9 C 0.5909(4) -0.0269(3) 0.2183(3) 0.0520(9) Uani 1 1 d . . . . .
H9 H 0.557189 -0.086130 0.271746 0.062 Uiso 1 1 calc R U . . .
C10 C 0.6976(5) -0.0728(3) 0.1105(3) 0.0576(10) Uani 1 1 d . . . . .
C11A C 0.8087(12) -0.1803(7) 0.1019(7) 0.067(2) Uani 0.507(5) 1 d . U P A 1
H11A H 0.820159 -0.226613 0.166960 0.081 Uiso 0.507(5) 1 calc R U P A 1
C12A C 0.9057(13) -0.2235(8) -0.0002(8) 0.078(3) Uani 0.507(5) 1 d . U P A 1
H12A H 0.985868 -0.294546 -0.001096 0.093 Uiso 0.507(5) 1 calc R U P A 1
C14A C 0.7558(12) -0.0698(8) -0.0953(7) 0.072(3) Uani 0.507(5) 1 d . U P A 1
H14A H 0.733440 -0.037488 -0.162799 0.086 Uiso 0.507(5) 1 calc R U P A 1
C15A C 0.6585(10) -0.0212(7) 0.0075(6) 0.066(2) Uani 0.507(5) 1 d . U P A 1
H15A H 0.569598 0.043853 0.008796 0.079 Uiso 0.507(5) 1 calc R U P A 1
C11 C 0.6959(13) -0.1747(8) 0.0827(8) 0.076(3) Uani 0.493(5) 1 d . U P A 2
H11 H 0.627915 -0.219855 0.132149 0.091 Uiso 0.493(5) 1 calc R U P A 2
C12 C 0.7901(15) -0.2224(9) -0.0176(10) 0.088(3) Uani 0.493(5) 1 d . U P A 2
H12 H 0.781240 -0.298048 -0.032105 0.105 Uiso 0.493(5) 1 calc R U P A 2
C14 C 0.9457(12) -0.0763(9) -0.0429(9) 0.095(3) Uani 0.493(5) 1 d . U P A 2
H14 H 1.044210 -0.054317 -0.078517 0.114 Uiso 0.493(5) 1 calc R U P A 2
C15 C 0.8463(10) -0.0255(8) 0.0561(7) 0.071(3) Uani 0.493(5) 1 d . U P A 2
H15 H 0.871877 0.035060 0.086738 0.085 Uiso 0.493(5) 1 calc R U P A 2
C13 C 0.8888(8) -0.1697(4) -0.0919(4) 0.1019(19) Uani 1 1 d . . . . .
H13 H 0.964554 -0.195911 -0.158240 0.122 Uiso 0.507(5) 1 calc R U P A 1
H13A H 0.922345 -0.186101 -0.167226 0.122 Uiso 0.493(5) 1 calc R U P A 2
C16 C 0.8143(4) 0.4470(3) 0.2418(3) 0.0412(7) Uani 1 1 d . . . . .
C17 C 0.9450(5) 0.4900(4) 0.1731(3) 0.0644(11) Uani 1 1 d . . . . .
H17 H 0.944192 0.516893 0.099837 0.077 Uiso 1 1 calc R U . . .
C18 C 1.0768(5) 0.4937(4) 0.2110(4) 0.0782(13) Uani 1 1 d . . . . .
H18 H 1.164552 0.522072 0.163124 0.094 Uiso 1 1 calc R U . . .
C19 C 1.0790(5) 0.4562(4) 0.3180(4) 0.0739(12) Uani 1 1 d . . . . .
H19 H 1.167450 0.459822 0.343870 0.089 Uiso 1 1 calc R U . . .
C20 C 0.9505(5) 0.4130(4) 0.3878(4) 0.0755(13) Uani 1 1 d . . . . .
H20 H 0.952064 0.387350 0.461254 0.091 Uiso 1 1 calc R U . . .
C21 C 0.8194(4) 0.4073(4) 0.3504(3) 0.0597(10) Uani 1 1 d . . . . .
H21 H 0.733661 0.376661 0.398198 0.072 Uiso 1 1 calc R U . . .
C22 C 0.4928(4) 0.5786(3) 0.2222(3) 0.0397(7) Uani 1 1 d . . . . .
C23 C 0.4188(5) 0.6410(3) 0.1419(3) 0.0635(10) Uani 1 1 d . . . . .
H23 H 0.451057 0.613502 0.069970 0.076 Uiso 1 1 calc R U . . .
C24 C 0.2965(6) 0.7444(4) 0.1680(5) 0.0862(15) Uani 1 1 d . . . . .
H24 H 0.247055 0.786504 0.113469 0.103 Uiso 1 1 calc R U . . .
C25 C 0.2484(5) 0.7849(4) 0.2733(5) 0.0744(13) Uani 1 1 d . . . . .
H25 H 0.167111 0.855036 0.290328 0.089 Uiso 1 1 calc R U . . .
C26 C 0.3191(6) 0.7227(4) 0.3536(4) 0.0691(12) Uani 1 1 d . . . . .
H26 H 0.284530 0.749949 0.425624 0.083 Uiso 1 1 calc R U . . .
C27 C 0.4415(5) 0.6196(3) 0.3292(3) 0.0554(9) Uani 1 1 d . . . . .
H27 H 0.489432 0.577831 0.384534 0.066 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 C5 1.902(3) . ?
S1 C1 1.745(3) . ?
S1 C8 1.767(3) . ?
P1 O1 1.476(2) . ?
P1 C22 1.791(3) . ?
P1 C16 1.795(3) . ?
P1 C1 1.837(3) . ?
C1 N1 1.274(4) . ?
N1 C2 1.410(4) . ?
C2 C3 1.393(4) . ?
C2 C7 1.402(5) . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(4) . ?
C6 C7 1.402(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.477(4) . ?
C8 C9 1.330(5) . ?
C9 C10 1.474(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.260(9) . ?
C10 C11A 1.357(9) . ?
C10 C15A 1.442(8) . ?
C10 C15 1.483(8) . ?
C11A C12A 1.385(11) . ?
C11A H11A 0.9300 . ?
C12A C13 1.260(10) . ?
C12A H12A 0.9300 . ?
C14A C15A 1.414(11) . ?
C14A C13 1.419(10) . ?
C14A H14A 0.9300 . ?
C15A H15A 0.9300 . ?
C11 C12 1.378(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.277(11) . ?
C12 H12 0.9300 . ?
C14 C15 1.390(12) . ?
C14 C13 1.535(12) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C13 H13A 0.9300 . ?
C16 C17 1.379(4) . ?
C16 C21 1.385(4) . ?
C17 C18 1.376(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.355(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.377(5) . ?
C22 C27 1.383(5) . ?
C23 C24 1.383(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.363(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.360(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.378(6) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

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 101.55(15) . . ?
O1 P1 C22 113.19(14) . . ?
O1 P1 C16 113.05(14) . . ?
C22 P1 C16 108.02(15) . . ?
O1 P1 C1 110.28(15) . . ?
C22 P1 C1 105.23(14) . . ?
C16 P1 C1 106.57(14) . . ?
N1 C1 S1 128.5(2) . . ?
N1 C1 P1 119.8(2) . . ?
S1 C1 P1 111.70(17) . . ?
C1 N1 C2 121.1(3) . . ?
C3 C2 C7 120.3(3) . . ?
C3 C2 N1 115.4(3) . . ?
C7 C2 N1 124.3(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 121.8(3) . . ?
C4 C5 Br1 119.9(2) . . ?
C6 C5 Br1 118.2(3) . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 117.4(3) . . ?
C2 C7 C8 122.9(3) . . ?
C6 C7 C8 119.7(3) . . ?
C9 C8 C7 123.6(3) . . ?
C9 C8 S1 120.1(3) . . ?
C7 C8 S1 116.3(2) . . ?
C8 C9 C10 130.1(3) . . ?
C8 C9 H9 115.0 . . ?
C10 C9 H9 115.0 . . ?
C11A C10 C15A 115.1(5) . . ?
C11 C10 C9 119.8(5) . . ?
C11A C10 C9 123.1(5) . . ?
C15A C10 C9 119.9(4) . . ?
C11 C10 C15 116.8(6) . . ?
C9 C10 C15 119.5(5) . . ?
C10 C11A C12A 122.5(7) . . ?
C10 C11A H11A 118.8 . . ?
C12A C11A H11A 118.8 . . ?
C13 C12A C11A 122.1(8) . . ?
C13 C12A H12A 118.9 . . ?
C11A C12A H12A 118.9 . . ?
C15A C14A C13 117.5(7) . . ?
C15A C14A H14A 121.2 . . ?
C13 C14A H14A 121.2 . . ?
C14A C15A C10 119.8(7) . . ?
C14A C15A H15A 120.1 . . ?
C10 C15A H15A 120.1 . . ?
C10 C11 C12 123.0(8) . . ?
C10 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C13 C12 C11 124.4(9) . . ?
C13 C12 H12 117.8 . . ?
C11 C12 H12 117.8 . . ?
C15 C14 C13 118.3(7) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C10 116.7(7) . . ?
C14 C15 H15 121.7 . . ?
C10 C15 H15 121.7 . . ?
C12A C13 C14A 121.0(6) . . ?
C12 C13 C14 112.5(7) . . ?
C12A C13 H13 119.5 . . ?
C14A C13 H13 119.5 . . ?
C12 C13 H13A 123.8 . . ?
C14 C13 H13A 123.8 . . ?
C17 C16 C21 118.0(3) . . ?
C17 C16 P1 116.7(3) . . ?
C21 C16 P1 125.3(2) . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.8(4) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.6(4) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.3(3) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C23 C22 C27 119.2(3) . . ?
C23 C22 P1 117.4(3) . . ?
C27 C22 P1 123.4(3) . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 120.2(4) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 120.0(4) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.7(4) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 119.8(4) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?

_refine_diff_density_max         0.347
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.081

