# Supplementary Information (SI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_240916lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2383214'
loop_
_audit_author_name
_audit_author_address
'Arulmozhi Velusamy'
;National Central University, Taiwan
Taiwan
;
_audit_update_record             
;
2024-09-11 deposited with the CCDC.	2025-02-17 downloaded from the CCDC.
;
_audit_creation_date             2024-09-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N O3 P S'
_chemical_formula_sum            'C16 H18 N O3 P S'
_chemical_formula_weight         335.34
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O P S'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, z+1/2'

_cell_length_a                   29.9399(3)
_cell_length_b                   13.61034(13)
_cell_length_c                   7.71770(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3144.90(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14999
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.8950
_cell_measurement_theta_min      5.4640
_shelx_estimated_absorpt_T_max   0.893
_shelx_estimated_absorpt_T_min   0.458
_exptl_absorpt_coefficient_mu    2.896
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20064
_diffrn_reflns_point_group_measured_fraction_full 0.843
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         3.567
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     63.00  93.00   0.50    0.05    --   56.31  30.00  30.00   60
  2  ω     63.00  88.00   0.50    0.05    --   56.31  30.00   0.00   50
  3  ω     90.00 122.00   0.50    0.05    --   83.08  30.00   0.00   64
  4  ω    105.00 133.00   0.50    0.05    --   83.08  30.00 -30.00   56
  5  ω     90.00 136.00   0.50    0.05    --   83.08  30.00 -60.00   92
  6  ω     99.00 124.00   0.50    0.05    --   83.08  30.00 150.00   50
  7  ω     95.00 134.00   0.50    0.05    --   83.08  30.00  90.00   78
  8  ω     90.00 136.00   0.50    0.05    --   83.08  30.00  60.00   92
  9  ω     50.00 110.00   0.50    0.05    --   83.08  15.00-120.00  120
 10  ω     41.00  92.00   0.50    0.05    --   83.08 -95.00-150.00  102
 11  ω     43.00  68.00   0.50    0.05    --   83.08-126.00-103.00   50
 12  ω     36.00  62.00   0.50    0.05    --   68.31-126.00-103.00   52
 13  ω     39.00  83.00   0.50    0.05    --   56.31-126.00-103.00   88
 14  ω     36.00  62.00   0.50    0.05    --   68.31 -95.00 -90.00   52
 15  ω     41.00  92.00   0.50    0.05    --   83.08 -95.00-180.00  102
 16  ω     43.00  84.00   0.50    0.05    --   83.08-111.00  30.00   82
 17  ω     49.00  87.00   0.50    0.05    --   83.08-111.00 150.00   76
 18  ω     24.00  49.00   0.50    0.05    --   68.31 -95.00 120.00   50
 19  ω     13.00  60.00   0.50    0.05    --   56.31 -95.00 150.00   94
 20  ω     41.00  66.00   0.50    0.05    --   83.08-111.00 120.00   50
 21  ω     39.00  92.00   0.50    0.05    --   83.08 -95.00  90.00  106
 22  ω     29.00  76.00   0.50    0.05    --   68.31 -95.00  60.00   94
 23  ω     41.00  85.00   0.50    0.05    --   83.08 -95.00  60.00   88
 24  ω     67.00  92.00   0.50    0.05    --   83.08 -95.00 -90.00   50
 25  ω     42.00  67.00   0.50    0.05    --   83.08 -95.00-120.00   50
 26  ω     12.00  44.00   0.50    0.05    --   56.31 -95.00 -60.00   64
 27  ω   -111.00 -65.00   0.50    0.05    --  -57.52 -30.00 -90.00   92
 28  ω   -105.00 -66.00   0.50    0.05    --  -57.52 -30.00-150.00   78
 29  ω   -123.00 -85.00   0.50    0.05    --  -77.69 -30.00 -30.00   76
 30  ω   -129.00 -87.00   0.50    0.05    --  -77.69 -30.00  60.00   84
 31  ω   -131.00 -85.00   0.50    0.05    --  -77.69 -30.00  90.00   92
 32  ω   -117.00 -90.00   0.50    0.05    --  -77.69 -30.00 120.00   54
 33  ω   -125.00-100.00   0.50    0.05    --  -77.69 -30.00 150.00   50
 34  ω   -109.00 -64.00   0.50    0.05    --  -57.52 -30.00 150.00   90
 35  ω   -130.00 -41.00   0.50    0.05    --  -77.69 -15.00-180.00  178
 36  ω    -93.00 -68.00   0.50    0.05    --  -80.00 101.00 -52.48   50
 37  ω    -54.00 -18.00   0.50    0.05    --  -57.52 126.00 -26.00   72
 38  ω    -58.00 -28.00   0.50    0.05    --  -68.85 126.00 -26.00   60
 39  ω    -60.00 -34.00   0.50    0.05    --  -77.69 111.00 -90.00   52
 40  ω    -97.00 -48.00   0.50    0.05    --  -81.75 114.00-142.32   98
 41  ω    -98.00 -37.00   0.50    0.05    --  -81.75 118.00-111.17  122
 42  ω    -88.00 -30.00   0.50    0.05    --  -77.69 111.00 -60.00  116
 43  ω   -101.00 -64.00   0.50    0.05    --  -77.69 126.00 -26.00   74
 44  ω    -92.00 -30.00   0.50    0.05    --  -77.69 111.00 120.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0216296000
_diffrn_orient_matrix_UB_12      0.1026852000
_diffrn_orient_matrix_UB_13      0.0023138000
_diffrn_orient_matrix_UB_21      0.0465609000
_diffrn_orient_matrix_UB_22      0.0473241000
_diffrn_orient_matrix_UB_23      0.0162214000
_diffrn_orient_matrix_UB_31      0.0035469000
_diffrn_orient_matrix_UB_32      0.0050592000
_diffrn_orient_matrix_UB_33      -0.1989356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.560
_reflns_Friedel_fraction_full    0.663
_reflns_Friedel_fraction_max     0.663
_reflns_number_gt                2337
_reflns_number_total             2368
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.027(18)
_refine_ls_extinction_coef       0.00040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0246
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+1.1702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0660
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised tetrahedral OH refined as rotating group:
 O20(H20), O21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S8 S 0.31255(2) 0.89869(4) 0.97132(10) 0.02532(18) Uani 1 1 d . . . . .
P19 P 0.44519(2) 0.59457(4) 0.08298(8) 0.01310(16) Uani 1 1 d . . . . .
O20 O 0.49370(5) 0.63038(11) 0.0394(2) 0.0181(4) Uani 1 1 d . . . . .
H20 H 0.512278 0.588932 0.075585 0.027 Uiso 1 1 calc R U . . .
O21 O 0.41694(5) 0.60273(11) -0.0844(2) 0.0180(4) Uani 1 1 d . . . . .
H21 H 0.427846 0.566121 -0.161145 0.027 Uiso 1 1 calc R U . . .
O22 O 0.44651(4) 0.49132(12) 0.1544(2) 0.0164(3) Uani 1 1 d . . . . .
N1 N 0.36403(6) 0.77811(13) 0.7255(3) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.39175(7) 0.83227(15) 0.8401(3) 0.0180(5) Uani 1 1 d . . . . .
C3 C 0.43835(8) 0.82895(17) 0.8347(4) 0.0207(5) Uani 1 1 d . . . . .
H3 H 0.452895 0.787288 0.753608 0.025 Uiso 1 1 calc R U . . .
C4 C 0.46372(9) 0.88658(18) 0.9478(4) 0.0270(6) Uani 1 1 d . . . . .
H4 H 0.495397 0.884980 0.941073 0.032 Uiso 1 1 calc R U . . .
C5 C 0.44313(9) 0.94594(18) 1.0696(4) 0.0318(6) Uani 1 1 d . . . . .
H5 H 0.460585 0.985167 1.145577 0.038 Uiso 1 1 calc R U . . .
C6 C 0.39692(9) 0.94792(16) 1.0801(4) 0.0283(6) Uani 1 1 d . . . . .
H6 H 0.382669 0.987200 1.165498 0.034 Uiso 1 1 calc R U . . .
C7 C 0.37141(8) 0.89236(16) 0.9655(4) 0.0218(5) Uani 1 1 d . . . . .
C9 C 0.30222(7) 0.77316(16) 0.9290(3) 0.0189(5) Uani 1 1 d . . . . .
C10 C 0.26837(8) 0.72398(19) 1.0166(4) 0.0235(5) Uani 1 1 d . . . . .
H10 H 0.251940 0.756688 1.104699 0.028 Uiso 1 1 calc R U . . .
C11 C 0.25861(7) 0.62733(19) 0.9755(4) 0.0262(6) Uani 1 1 d . . . . .
H11 H 0.234801 0.594214 1.032112 0.031 Uiso 1 1 calc R U . . .
C12 C 0.28381(8) 0.57926(18) 0.8511(4) 0.0243(6) Uani 1 1 d . . . . .
H12 H 0.277066 0.513027 0.822394 0.029 Uiso 1 1 calc R U . . .
C13 C 0.31890(8) 0.62682(17) 0.7677(4) 0.0193(5) Uani 1 1 d . . . . .
H13 H 0.336444 0.592385 0.685034 0.023 Uiso 1 1 calc R U . . .
C14 C 0.32840(7) 0.72508(15) 0.8052(3) 0.0162(5) Uani 1 1 d . . . . .
C15 C 0.38511(7) 0.73543(15) 0.5724(3) 0.0173(5) Uani 1 1 d . . . . .
H15A H 0.396069 0.668868 0.601931 0.021 Uiso 1 1 calc R U . . .
H15B H 0.411349 0.775899 0.540765 0.021 Uiso 1 1 calc R U . . .
C16 C 0.35427(7) 0.72786(17) 0.4153(3) 0.0194(5) Uani 1 1 d . . . . .
H16A H 0.351276 0.793260 0.360333 0.023 Uiso 1 1 calc R U . . .
H16B H 0.324232 0.706364 0.453236 0.023 Uiso 1 1 calc R U . . .
C17 C 0.37278(7) 0.65466(17) 0.2835(3) 0.0167(5) Uani 1 1 d . . . . .
H17A H 0.353352 0.654338 0.179659 0.020 Uiso 1 1 calc R U . . .
H17B H 0.372233 0.587896 0.334323 0.020 Uiso 1 1 calc R U . . .
C18 C 0.42099(7) 0.67985(15) 0.2285(3) 0.0161(5) Uani 1 1 d . . . . .
H18A H 0.439866 0.683614 0.333653 0.019 Uiso 1 1 calc R U . . .
H18B H 0.421063 0.745597 0.173661 0.019 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
S8 C7 1.765(2) . ?
S8 C9 1.767(2) . ?
P19 O20 1.5682(15) . ?
P19 O21 1.5482(18) . ?
P19 O22 1.5099(17) . ?
P19 C18 1.770(2) . ?
O20 H20 0.8400 . ?
O21 H21 0.8400 . ?
N1 C2 1.419(3) . ?
N1 C14 1.427(3) . ?
N1 C15 1.460(3) . ?
C2 C3 1.397(3) . ?
C2 C7 1.406(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(4) . ?
C9 C10 1.390(3) . ?
C9 C14 1.399(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.528(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.528(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.543(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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
C7 S8 C9 97.06(10) . . ?
O20 P19 C18 108.13(9) . . ?
O21 P19 O20 107.75(10) . . ?
O21 P19 C18 105.00(10) . . ?
O22 P19 O20 110.08(8) . . ?
O22 P19 O21 112.68(9) . . ?
O22 P19 C18 112.91(10) . . ?
P19 O20 H20 109.5 . . ?
P19 O21 H21 109.5 . . ?
C2 N1 C14 115.54(19) . . ?
C2 N1 C15 117.28(18) . . ?
C14 N1 C15 118.06(18) . . ?
C3 C2 N1 123.3(2) . . ?
C3 C2 C7 118.2(2) . . ?
C7 C2 N1 118.6(2) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 S8 118.57(19) . . ?
C6 C7 S8 120.4(2) . . ?
C6 C7 C2 121.0(2) . . ?
C10 C9 S8 120.22(18) . . ?
C10 C9 C14 121.1(2) . . ?
C14 C9 S8 118.73(18) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.5(2) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 N1 118.5(2) . . ?
C13 C14 N1 123.2(2) . . ?
C13 C14 C9 118.4(2) . . ?
N1 C15 H15A 108.7 . . ?
N1 C15 H15B 108.7 . . ?
N1 C15 C16 114.07(17) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 C17 110.68(18) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C16 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C16 C17 C18 112.17(18) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
P19 C18 H18A 108.7 . . ?
P19 C18 H18B 108.7 . . ?
C17 C18 P19 114.30(15) . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?

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
S8 C9 C10 C11 176.1(2) . . . . ?
S8 C9 C14 N1 3.5(3) . . . . ?
S8 C9 C14 C13 -177.60(18) . . . . ?
O20 P19 C18 C17 179.79(16) . . . . ?
O21 P19 C18 C17 64.97(18) . . . . ?
O22 P19 C18 C17 -58.16(19) . . . . ?
N1 C2 C3 C4 178.0(2) . . . . ?
N1 C2 C7 S8 -1.0(3) . . . . ?
N1 C2 C7 C6 -179.3(2) . . . . ?
N1 C15 C16 C17 -161.70(18) . . . . ?
C2 N1 C14 C9 46.4(3) . . . . ?
C2 N1 C14 C13 -132.4(2) . . . . ?
C2 N1 C15 C16 -149.08(19) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C3 C2 C7 S8 178.99(18) . . . . ?
C3 C2 C7 C6 0.7(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 -1.7(4) . . . . ?
C5 C6 C7 S8 -177.1(2) . . . . ?
C5 C6 C7 C2 1.2(4) . . . . ?
C7 S8 C9 C10 139.8(2) . . . . ?
C7 S8 C9 C14 -40.8(2) . . . . ?
C7 C2 C3 C4 -2.0(4) . . . . ?
C9 S8 C7 C2 39.5(2) . . . . ?
C9 S8 C7 C6 -142.2(2) . . . . ?
C9 C10 C11 C12 2.3(4) . . . . ?
C10 C9 C14 N1 -177.0(2) . . . . ?
C10 C9 C14 C13 1.8(3) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 -1.8(4) . . . . ?
C12 C13 C14 N1 179.5(2) . . . . ?
C12 C13 C14 C9 0.7(4) . . . . ?
C14 N1 C2 C3 132.2(2) . . . . ?
C14 N1 C2 C7 -47.8(3) . . . . ?
C14 N1 C15 C16 65.4(3) . . . . ?
C14 C9 C10 C11 -3.4(4) . . . . ?
C15 N1 C2 C3 -14.2(3) . . . . ?
C15 N1 C2 C7 165.8(2) . . . . ?
C15 N1 C14 C9 -167.4(2) . . . . ?
C15 N1 C14 C13 13.7(3) . . . . ?
C15 C16 C17 C18 -55.1(3) . . . . ?
C16 C17 C18 P19 177.37(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.641
####################################################################### 
# 
# 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_241020lt_auto
_database_code_depnum_ccdc_archive 'CCDC 2389332'
loop_
_audit_author_name
_audit_author_address
'Arulmozhi Velusamy'
;National Central University, Taiwan
Taiwan
;
_audit_update_record             
;
2024-10-08 deposited with the CCDC.	2025-02-17 downloaded from the CCDC.
;
_audit_creation_date             2024-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Br2 N O3 P S'
_chemical_formula_sum            'C16 H16 Br2 N O3 P S'
_chemical_formula_weight         493.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N S Br P O '
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'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   38.4715(5)
_cell_length_b                   8.07574(11)
_cell_length_c                   11.33025(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.3729(12)
_cell_angle_gamma                90
_cell_volume                     3519.13(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6771
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      72.5820
_cell_measurement_theta_min      4.5530
_shelx_estimated_absorpt_T_max   0.857
_shelx_estimated_absorpt_T_min   0.569
_exptl_absorpt_coefficient_mu    7.953
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10590
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.843
_diffrn_reflns_theta_min         4.599
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -72.00   0.50    0.05    --  -57.37 -30.00   0.00   68
  2  ω   -130.00 -95.00   0.50    0.05    --  -77.69 -30.00   0.00   70
  3  ω   -127.00 -91.00   0.50    0.05    --  -77.69 -30.00 -60.00   72
  4  ω   -121.00 -95.00   0.50    0.05    --  -68.63 -30.00-150.00   52
  5  ω   -127.00-102.00   0.50    0.05    --  -77.69 -30.00-150.00   50
  6  ω   -131.00-106.00   0.50    0.05    --  -77.69 -30.00  30.00   50
  7  ω   -128.00-102.00   0.50    0.05    --  -77.69 -30.00  60.00   52
  8  ω   -130.00-104.00   0.50    0.05    --  -77.69 -15.00  90.00   52
  9  ω    -97.00 -49.00   0.50    0.05    --  -77.69 -15.00  90.00   96
 10  ω    -78.00 -32.00   0.50    0.05    --  -77.69 111.00  30.00   92
 11  ω    -84.00 -31.00   0.50    0.05    --  -77.69 111.00  60.00  106
 12  ω    -92.00 -31.00   0.50    0.05    --  -77.69 111.00 -90.00  122
 13  ω     78.00 108.00   0.50    0.05    --   68.01  30.00 -90.00   60
 14  ω     55.00  81.00   0.50    0.05    --   83.08  15.00  30.00   52
 15  ω     90.00 130.00   0.50    0.05    --   83.08  15.00  30.00   80
 16  ω     90.00 134.00   0.50    0.05    --   83.08  30.00 150.00   88
 17  ω     58.00  83.00   0.50    0.05    --   83.08 -95.00 -30.00   50
 18  ω     41.00  72.00   0.50    0.05    --   83.08 -95.00-180.00   62
 19  ω     28.00  55.00   0.50    0.05    --   56.11-125.00-150.00   54
 20  ω     38.00  89.00   0.50    0.05    --   83.08 -95.00 -90.00  102
 21  ω     50.00  79.00   0.50    0.05    --   83.08 -95.00  30.00   58
 22  ω     54.00  81.00   0.50    0.05    --   83.08 -95.00 120.00   54
 23  ω     23.00  50.00   0.50    0.05    --   56.11-125.00 150.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0335673000
_diffrn_orient_matrix_UB_12      -0.0152147000
_diffrn_orient_matrix_UB_13      -0.0706742000
_diffrn_orient_matrix_UB_21      0.0133653000
_diffrn_orient_matrix_UB_22      0.1636154000
_diffrn_orient_matrix_UB_23      0.0542381000
_diffrn_orient_matrix_UB_31      0.0172993000
_diffrn_orient_matrix_UB_32      -0.0968917000
_diffrn_orient_matrix_UB_33      0.1027620000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3143
_reflns_number_total             3386
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.000067(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0266P)²+8.6997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0615
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14)
2.c Idealised tetrahedral OH refined as rotating group:
 O23(H23), O24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br15 Br 0.48059(2) 0.80828(4) 0.59910(2) 0.02654(9) Uani 1 1 d . . . . .
Br16 Br 0.62012(2) 0.82688(3) -0.14541(2) 0.02121(8) Uani 1 1 d . . . . .
S3 S 0.56342(2) 0.54122(7) 0.25279(5) 0.01684(13) Uani 1 1 d . . . . .
P21 P 0.73495(2) 0.65328(7) 0.83180(5) 0.01502(13) Uani 1 1 d . . . . .
O22 O 0.73614(4) 0.8341(2) 0.86324(14) 0.0184(3) Uani 1 1 d . . . . .
O23 O 0.76682(4) 0.6122(2) 0.75392(15) 0.0205(4) Uani 1 1 d . . . . .
H23 H 0.764230 0.517754 0.723981 0.031 Uiso 1 1 calc R U . . .
O24 O 0.73612(5) 0.5402(2) 0.94338(14) 0.0232(4) Uani 1 1 d . . . . .
H24 H 0.745909 0.590991 0.999674 0.035 Uiso 1 1 calc R U . . .
N10 N 0.62289(5) 0.6950(2) 0.38473(17) 0.0151(4) Uani 1 1 d . . . . .
C1 C 0.59010(5) 0.7251(3) 0.43780(19) 0.0144(4) Uani 1 1 d . . . . .
C2 C 0.55989(6) 0.6585(3) 0.3834(2) 0.0156(4) Uani 1 1 d . . . . .
C4 C 0.59647(6) 0.6609(3) 0.1891(2) 0.0146(4) Uani 1 1 d . . . . .
C5 C 0.59558(6) 0.6897(3) 0.0684(2) 0.0166(5) Uani 1 1 d . . . . .
H5 H 0.576555 0.651494 0.020768 0.020 Uiso 1 1 calc R U . . .
C6 C 0.62275(6) 0.7750(3) 0.01789(19) 0.0159(5) Uani 1 1 d . . . . .
C7 C 0.65085(6) 0.8291(3) 0.0860(2) 0.0157(5) Uani 1 1 d . . . . .
H7 H 0.669922 0.881887 0.049836 0.019 Uiso 1 1 calc R U . . .
C8 C 0.65100(6) 0.8057(3) 0.2070(2) 0.0157(5) Uani 1 1 d . . . . .
H8 H 0.669847 0.847261 0.253872 0.019 Uiso 1 1 calc R U . . .
C9 C 0.62379(6) 0.7218(3) 0.2616(2) 0.0143(4) Uani 1 1 d . . . . .
C11 C 0.58646(6) 0.8193(3) 0.5393(2) 0.0158(5) Uani 1 1 d . . . . .
H11 H 0.606451 0.868641 0.575372 0.019 Uiso 1 1 calc R U . . .
C12 C 0.55423(6) 0.8429(3) 0.5891(2) 0.0182(5) Uani 1 1 d . . . . .
H12 H 0.552217 0.905775 0.659441 0.022 Uiso 1 1 calc R U . . .
C13 C 0.52505(6) 0.7738(3) 0.5349(2) 0.0179(5) Uani 1 1 d . . . . .
C14 C 0.52734(6) 0.6834(3) 0.4315(2) 0.0171(5) Uani 1 1 d . . . . .
H14 H 0.507033 0.639087 0.394084 0.021 Uiso 1 1 calc R U . . .
C17 C 0.65447(5) 0.7363(3) 0.45487(19) 0.0144(4) Uani 1 1 d . . . . .
H17A H 0.653560 0.854728 0.477169 0.017 Uiso 1 1 calc R U . . .
H17B H 0.675013 0.720439 0.405125 0.017 Uiso 1 1 calc R U . . .
C18 C 0.65910(5) 0.6324(3) 0.5668(2) 0.0161(5) Uani 1 1 d . . . . .
H18A H 0.663262 0.515374 0.545395 0.019 Uiso 1 1 calc R U . . .
H18B H 0.637686 0.637617 0.613381 0.019 Uiso 1 1 calc R U . . .
C19 C 0.68989(6) 0.6980(3) 0.6407(2) 0.0162(5) Uani 1 1 d . . . . .
H19A H 0.685058 0.813325 0.665001 0.019 Uiso 1 1 calc R U . . .
H19B H 0.710904 0.699161 0.591922 0.019 Uiso 1 1 calc R U . . .
C20 C 0.69691(5) 0.5917(3) 0.75105(19) 0.0158(5) Uani 1 1 d . . . . .
H20A H 0.699392 0.474565 0.726925 0.019 Uiso 1 1 calc R U . . .
H20B H 0.676668 0.599219 0.803119 0.019 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
Br15 C13 1.895(2) . ?
Br16 C6 1.898(2) . ?
S3 C2 1.765(2) . ?
S3 C4 1.765(2) . ?
P21 O22 1.5034(17) . ?
P21 O23 1.5634(16) . ?
P21 O24 1.5594(17) . ?
P21 C20 1.778(2) . ?
O23 H23 0.8400 . ?
O24 H24 0.8400 . ?
N10 C1 1.431(3) . ?
N10 C9 1.413(3) . ?
N10 C17 1.474(3) . ?
C1 C2 1.409(3) . ?
C1 C11 1.389(3) . ?
C2 C14 1.392(3) . ?
C4 C5 1.388(3) . ?
C4 C9 1.407(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(3) . ?
C6 C7 1.383(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.403(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 C14 1.385(3) . ?
C14 H14 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.527(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.529(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.535(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
C2 S3 C4 96.87(11) . . ?
O22 P21 O23 108.65(10) . . ?
O22 P21 O24 112.12(9) . . ?
O22 P21 C20 114.43(10) . . ?
O23 P21 C20 107.30(10) . . ?
O24 P21 O23 109.00(10) . . ?
O24 P21 C20 105.12(10) . . ?
P21 O23 H23 109.5 . . ?
P21 O24 H24 109.5 . . ?
C1 N10 C17 117.28(18) . . ?
C9 N10 C1 115.56(17) . . ?
C9 N10 C17 117.27(18) . . ?
C2 C1 N10 118.5(2) . . ?
C11 C1 N10 123.3(2) . . ?
C11 C1 C2 118.2(2) . . ?
C1 C2 S3 119.48(18) . . ?
C14 C2 S3 119.61(18) . . ?
C14 C2 C1 120.9(2) . . ?
C5 C4 S3 119.61(17) . . ?
C5 C4 C9 121.1(2) . . ?
C9 C4 S3 119.23(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
C5 C6 Br16 119.25(17) . . ?
C7 C6 Br16 119.77(17) . . ?
C7 C6 C5 120.9(2) . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(2) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C4 C9 N10 119.1(2) . . ?
C8 C9 N10 123.1(2) . . ?
C8 C9 C4 117.8(2) . . ?
C1 C11 H11 119.3 . . ?
C12 C11 C1 121.4(2) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 Br15 120.04(18) . . ?
C12 C13 C14 121.4(2) . . ?
C14 C13 Br15 118.58(17) . . ?
C2 C14 H14 120.5 . . ?
C13 C14 C2 118.9(2) . . ?
C13 C14 H14 120.5 . . ?
N10 C17 H17A 108.8 . . ?
N10 C17 H17B 108.8 . . ?
N10 C17 C18 113.68(18) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
C17 C18 C19 109.76(18) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
C18 C19 C20 111.78(18) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
P21 C20 H20A 109.0 . . ?
P21 C20 H20B 109.0 . . ?
C19 C20 P21 112.90(16) . . ?
C19 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?

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
Br15 C13 C14 C2 179.59(17) . . . . ?
Br16 C6 C7 C8 173.44(17) . . . . ?
S3 C2 C14 C13 179.16(18) . . . . ?
S3 C4 C5 C6 -175.98(17) . . . . ?
S3 C4 C9 N10 -4.1(3) . . . . ?
S3 C4 C9 C8 175.26(17) . . . . ?
O22 P21 C20 C19 52.79(19) . . . . ?
O23 P21 C20 C19 -67.83(19) . . . . ?
O24 P21 C20 C19 176.23(16) . . . . ?
N10 C1 C2 S3 0.0(3) . . . . ?
N10 C1 C2 C14 179.7(2) . . . . ?
N10 C1 C11 C12 -178.8(2) . . . . ?
N10 C17 C18 C19 -173.17(19) . . . . ?
C1 N10 C9 C4 -44.8(3) . . . . ?
C1 N10 C9 C8 135.8(2) . . . . ?
C1 N10 C17 C18 64.3(3) . . . . ?
C1 C2 C14 C13 -0.6(3) . . . . ?
C1 C11 C12 C13 -1.4(3) . . . . ?
C2 S3 C4 C5 -141.66(19) . . . . ?
C2 S3 C4 C9 40.0(2) . . . . ?
C2 C1 C11 C12 2.4(3) . . . . ?
C4 S3 C2 C1 -37.7(2) . . . . ?
C4 S3 C2 C14 142.55(19) . . . . ?
C4 C5 C6 Br16 -175.96(17) . . . . ?
C4 C5 C6 C7 1.0(3) . . . . ?
C5 C4 C9 N10 177.5(2) . . . . ?
C5 C4 C9 C8 -3.1(3) . . . . ?
C5 C6 C7 C8 -3.5(3) . . . . ?
C6 C7 C8 C9 2.7(3) . . . . ?
C7 C8 C9 N10 179.9(2) . . . . ?
C7 C8 C9 C4 0.5(3) . . . . ?
C9 N10 C1 C2 47.1(3) . . . . ?
C9 N10 C1 C11 -131.7(2) . . . . ?
C9 N10 C17 C18 -151.4(2) . . . . ?
C9 C4 C5 C6 2.3(3) . . . . ?
C11 C1 C2 S3 178.85(17) . . . . ?
C11 C1 C2 C14 -1.4(3) . . . . ?
C11 C12 C13 Br15 -178.62(17) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C2 1.7(4) . . . . ?
C17 N10 C1 C2 -168.0(2) . . . . ?
C17 N10 C1 C11 13.2(3) . . . . ?
C17 N10 C9 C4 170.3(2) . . . . ?
C17 N10 C9 C8 -9.1(3) . . . . ?
C17 C18 C19 C20 -176.86(19) . . . . ?
C18 C19 C20 P21 174.61(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.663
_oxdiff_exptl_absorpt_empirical_full_min 0.807
