# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_p20201015a1
_database_code_depnum_ccdc_archive 'CCDC 2041102'
_audit_update_record             
;
2020-10-28 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_audit_creation_date             2020-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H36 Br O3 P'
_chemical_formula_sum            'C28 H36 Br O3 P'
_chemical_formula_weight         531.45
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.15691(7)
_cell_length_b                   16.71291(19)
_cell_length_c                   17.53844(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2684.06(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13445
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      78.8840
_cell_measurement_theta_min      5.0310
_shelx_estimated_absorpt_T_max   0.691
_shelx_estimated_absorpt_T_min   0.628
_exptl_absorpt_coefficient_mu    2.851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19439
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.270
_diffrn_reflns_theta_min         3.653
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  39.00   0.50    0.50    --    5.00 -32.00 -32.00  246
  2  ω    -29.00  94.00   0.50    0.50    --    5.00  32.00 127.00  246
  3  ω   -139.00 -15.00   0.50    0.50    --  -49.60 -32.00 -32.00  248
  4  ω   -166.00-114.00   0.50    2.00    -- -110.00 -32.00 -32.00  104
  5  ω   -107.00 -82.00   0.50    2.00    -- -110.00  32.00 127.00   50
  6  ω    -80.00  40.00   0.50    0.50    --  -49.60  38.00-120.00  240
  7  ω    -57.00 -20.00   0.50    0.50    --  -49.60 -57.00-180.00   74
  8  ω    -99.00 -60.00   0.50    0.50    --  -49.60 -57.00-180.00   78
  9  ω   -154.00 -81.00   0.50    2.00    -- -110.00 -57.00 -30.00  146
 10  ω    -80.00 -52.00   0.50    2.00    -- -110.00  38.00   0.00   56
 11  ω   -118.00 -46.00   0.50    2.00    -- -110.00  72.00 -90.00  144
 12  ω   -129.00 -91.00   0.50    2.00    -- -110.00 -57.00  60.00   76
 13  ω   -196.00-136.00   0.50    2.00    -- -110.00 -57.00  60.00  120
 14  ω   -115.00 -89.00   0.50    2.00    -- -110.00  38.00   0.00   52
 15  ω   -139.00 -24.00   0.50    2.00    -- -110.00  57.00  90.00  230
 16  ω   -138.00 -38.00   0.50    2.00    -- -110.00  57.00 -30.00  200
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1120509000
_diffrn_orient_matrix_UB_12      0.0638006000
_diffrn_orient_matrix_UB_13      -0.0246247000
_diffrn_orient_matrix_UB_21      -0.1049749000
_diffrn_orient_matrix_UB_22      -0.0665590000
_diffrn_orient_matrix_UB_23      -0.0264323000
_diffrn_orient_matrix_UB_31      -0.0688394000
_diffrn_orient_matrix_UB_32      -0.0023536000
_diffrn_orient_matrix_UB_33      0.0799981000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                5215
_reflns_number_total             5564
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 2030 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.031(12)
_refine_ls_extinction_coef       0.00050(16)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         5564
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.040
_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)+(0.0568P)²+0.5219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1094
_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 C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Br1) \\sim Ueq, Uanis(Br1A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(H22)=Sof(Br1A)=1-FVAR(1)
 Sof(H13)=Sof(Br1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C3(H3A), C5(H5), C8(H8), C17(H17), C26(H26)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
4.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C22(H22), C23(H23), C25(H25)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
P1 P -0.06452(9) -0.42733(6) -0.31453(5) 0.0628(2) Uani 1 1 d . . . . .
O1 O -0.1899(3) -0.4351(2) -0.37036(16) 0.0841(8) Uani 1 1 d . . . . .
O2 O -0.1346(5) -0.5847(3) -0.3978(2) 0.1131(13) Uani 1 1 d . . . . .
H2 H -0.176308 -0.541692 -0.392479 0.170 Uiso 1 1 calc GR . . . .
O3 O -0.3708(3) -0.3636(2) -0.27664(17) 0.0856(8) Uani 1 1 d . . . . .
H3 H -0.334380 -0.383509 -0.314924 0.128 Uiso 1 1 calc GR . . . .
C1 C 0.0531(4) -0.3436(2) -0.34243(16) 0.0600(7) Uani 1 1 d . . . . .
C2 C 0.1445(5) -0.3685(3) -0.4126(2) 0.0799(10) Uani 1 1 d . . . . .
H2A H 0.210062 -0.411799 -0.398854 0.096 Uiso 1 1 calc R . . . .
H2B H 0.080431 -0.387383 -0.452804 0.096 Uiso 1 1 calc R . . . .
C3 C 0.2324(5) -0.2970(3) -0.4408(3) 0.0883(13) Uani 1 1 d . . . . .
H3A H 0.290598 -0.313350 -0.485029 0.106 Uiso 1 1 calc R . . . .
C4 C 0.1326(6) -0.2301(3) -0.4638(3) 0.0949(14) Uani 1 1 d . . . . .
H4A H 0.069078 -0.247759 -0.504752 0.114 Uiso 1 1 calc R . . . .
H4B H 0.189693 -0.185188 -0.482186 0.114 Uiso 1 1 calc R . . . .
C5 C 0.0424(6) -0.2046(3) -0.3966(3) 0.0876(12) Uani 1 1 d . . . . .
H5 H -0.023002 -0.161036 -0.411922 0.105 Uiso 1 1 calc R . . . .
C6 C -0.0486(4) -0.2748(3) -0.3665(3) 0.0796(10) Uani 1 1 d . . . . .
H6A H -0.114819 -0.293226 -0.405995 0.095 Uiso 1 1 calc R . . . .
H6B H -0.106399 -0.257515 -0.323222 0.095 Uiso 1 1 calc R . . . .
C7 C 0.1556(5) -0.3132(3) -0.2797(2) 0.0767(10) Uani 1 1 d . . . . .
H7A H 0.099069 -0.297016 -0.235572 0.092 Uiso 1 1 calc R . . . .
H7B H 0.221312 -0.355770 -0.264249 0.092 Uiso 1 1 calc R . . . .
C8 C 0.2438(6) -0.2421(3) -0.3095(3) 0.0880(12) Uani 1 1 d . . . . .
H8 H 0.308946 -0.222967 -0.269131 0.106 Uiso 1 1 calc R . . . .
C9 C 0.3350(5) -0.2686(3) -0.3778(3) 0.0971(14) Uani 1 1 d . . . . .
H9A H 0.400090 -0.311617 -0.362963 0.116 Uiso 1 1 calc R . . . .
H9B H 0.393705 -0.224201 -0.395998 0.116 Uiso 1 1 calc R . . . .
C10 C 0.1433(7) -0.1753(3) -0.3332(3) 0.0969(14) Uani 1 1 d . . . . .
H10A H 0.200326 -0.130138 -0.351251 0.116 Uiso 1 1 calc R . . . .
H10B H 0.085845 -0.157773 -0.289879 0.116 Uiso 1 1 calc R . . . .
C11 C 0.0383(5) -0.5189(2) -0.31271(19) 0.0684(8) Uani 1 1 d . . . . .
C12 C -0.0091(6) -0.5850(3) -0.3559(2) 0.0841(12) Uani 1 1 d . . . . .
C13 C 0.0724(8) -0.6537(3) -0.3563(3) 0.0977(15) Uani 1 1 d . . . . .
H13 H 0.041739 -0.697117 -0.385397 0.117 Uiso 0.8949(18) 1 calc R . P A 1
C14 C 0.1985(7) -0.6596(3) -0.3143(3) 0.0954(16) Uani 1 1 d . . . . .
H14 H 0.251395 -0.707082 -0.315660 0.114 Uiso 1 1 calc R . . . .
C15 C 0.2487(5) -0.5972(2) -0.2704(2) 0.0793(11) Uani 1 1 d . . . . .
C16 C 0.1674(5) -0.5275(2) -0.2712(2) 0.0711(9) Uani 1 1 d . . . . .
H16 H 0.200320 -0.484224 -0.242600 0.085 Uiso 1 1 calc R . . . .
C17 C 0.3901(6) -0.6036(3) -0.2263(3) 0.0962(15) Uani 1 1 d . . . . .
H17 H 0.412480 -0.660863 -0.224110 0.115 Uiso 1 1 calc R . . . .
C18 C 0.5159(9) -0.5657(5) -0.2686(5) 0.141(3) Uani 1 1 d . . . . .
H18A H 0.532975 -0.594439 -0.315156 0.212 Uiso 1 1 calc GR . . . .
H18B H 0.601987 -0.567645 -0.237442 0.212 Uiso 1 1 calc GR . . . .
H18C H 0.492635 -0.511033 -0.280100 0.212 Uiso 1 1 calc GR . . . .
C19 C 0.3766(9) -0.5772(5) -0.1454(4) 0.140(3) Uani 1 1 d . . . . .
H19A H 0.373477 -0.519843 -0.143371 0.211 Uiso 1 1 calc GR . . . .
H19B H 0.459196 -0.596144 -0.116913 0.211 Uiso 1 1 calc GR . . . .
H19C H 0.288579 -0.598687 -0.123880 0.211 Uiso 1 1 calc GR . . . .
C20 C -0.1408(4) -0.4069(2) -0.22135(19) 0.0617(7) Uani 1 1 d . . . . .
C21 C -0.2832(4) -0.3780(2) -0.2155(2) 0.0636(8) Uani 1 1 d . . . . .
C22 C -0.3384(4) -0.3625(2) -0.1428(2) 0.0693(8) Uani 1 1 d . . . . .
H22 H -0.433736 -0.344014 -0.138023 0.083 Uiso 0.1051(18) 1 calc R . P A 2
C23 C -0.2574(5) -0.3733(2) -0.0793(2) 0.0707(9) Uani 1 1 d . . . . .
H23 H -0.297750 -0.361314 -0.031978 0.085 Uiso 1 1 calc R . . . .
C24 C -0.1154(4) -0.4021(2) -0.0830(2) 0.0667(8) Uani 1 1 d . . . . .
C25 C -0.0607(4) -0.4192(2) -0.15439(18) 0.0667(8) Uani 1 1 d . . . . .
H25 H 0.033331 -0.439777 -0.158218 0.080 Uiso 1 1 calc R . . . .
C26 C -0.0259(6) -0.4125(3) -0.0113(2) 0.0871(12) Uani 1 1 d . . . . .
H26 H -0.083412 -0.390951 0.031161 0.105 Uiso 1 1 calc R . . . .
C27 C 0.1142(9) -0.3649(7) -0.0154(4) 0.176(5) Uani 1 1 d . . . . .
H27A H 0.161534 -0.374842 -0.063287 0.264 Uiso 1 1 calc GR . . . .
H27B H 0.177686 -0.380652 0.025527 0.264 Uiso 1 1 calc GR . . . .
H27C H 0.092467 -0.308875 -0.010964 0.264 Uiso 1 1 calc GR . . . .
C28 C 0.0007(12) -0.4990(5) 0.0051(4) 0.151(3) Uani 1 1 d . . . . .
H28A H -0.090662 -0.527085 0.005622 0.226 Uiso 1 1 calc GR . . . .
H28B H 0.047409 -0.504292 0.053802 0.226 Uiso 1 1 calc GR . . . .
H28C H 0.062616 -0.521077 -0.033781 0.226 Uiso 1 1 calc GR . . . .
Br1 Br -0.53153(5) -0.32252(4) -0.13450(4) 0.0989(2) Uani 0.8949(18) 1 d . U P
A 1
Br1A Br -0.0133(8) -0.7252(2) -0.4149(3) 0.099(2) Uani 0.1051(18) 1 d . U P A 2


_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
P1 O1 1.515(3) . ?
P1 C1 1.833(4) . ?
P1 C11 1.797(4) . ?
P1 C20 1.810(4) . ?
O2 H2 0.8200 . ?
O2 C12 1.363(6) . ?
O3 H3 0.8200 . ?
O3 C21 1.360(4) . ?
C1 C2 1.546(5) . ?
C1 C6 1.538(5) . ?
C1 C7 1.533(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.523(7) . ?
C3 H3A 0.9800 . ?
C3 C4 1.500(7) . ?
C3 C9 1.526(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.502(7) . ?
C5 H5 0.9800 . ?
C5 C6 1.533(6) . ?
C5 C10 1.526(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.528(6) . ?
C8 H8 0.9800 . ?
C8 C9 1.525(8) . ?
C8 C10 1.506(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.408(5) . ?
C11 C16 1.397(6) . ?
C12 C13 1.371(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(8) . ?
C13 Br1A 1.760(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(7) . ?
C15 C16 1.382(6) . ?
C15 C17 1.511(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9800 . ?
C17 C18 1.509(9) . ?
C17 C19 1.490(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.394(5) . ?
C20 C25 1.399(5) . ?
C21 C22 1.396(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.351(6) . ?
C22 Br1 1.896(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.388(6) . ?
C24 C25 1.378(5) . ?
C24 C26 1.512(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9800 . ?
C26 C27 1.512(9) . ?
C26 C28 1.493(9) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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 109.78(16) . . ?
O1 P1 C11 109.60(18) . . ?
O1 P1 C20 107.91(17) . . ?
C11 P1 C1 110.34(17) . . ?
C11 P1 C20 110.29(16) . . ?
C20 P1 C1 108.89(16) . . ?
C12 O2 H2 109.5 . . ?
C21 O3 H3 109.5 . . ?
C2 C1 P1 108.9(3) . . ?
C6 C1 P1 106.8(2) . . ?
C6 C1 C2 108.1(3) . . ?
C7 C1 P1 114.9(2) . . ?
C7 C1 C2 109.2(3) . . ?
C7 C1 C6 108.7(3) . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 C1 109.4(4) . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 C9 109.6(4) . . ?
C4 C3 C2 110.5(4) . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 C9 109.7(4) . . ?
C9 C3 H3A 109.0 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C3 C4 C5 109.6(4) . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C4 C5 H5 109.3 . . ?
C4 C5 C6 110.6(4) . . ?
C4 C5 C10 109.2(4) . . ?
C6 C5 H5 109.3 . . ?
C10 C5 H5 109.3 . . ?
C10 C5 C6 109.0(4) . . ?
C1 C6 H6A 109.7 . . ?
C1 C6 H6B 109.7 . . ?
C5 C6 C1 109.7(3) . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C1 C7 H7A 109.8 . . ?
C1 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 C1 109.6(3) . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C7 C8 H8 109.2 . . ?
C9 C8 C7 109.4(4) . . ?
C9 C8 H8 109.2 . . ?
C10 C8 C7 110.4(4) . . ?
C10 C8 H8 109.2 . . ?
C10 C8 C9 109.4(4) . . ?
C3 C9 H9A 109.9 . . ?
C3 C9 H9B 109.9 . . ?
C8 C9 C3 108.8(4) . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C5 C10 H10A 109.8 . . ?
C5 C10 H10B 109.8 . . ?
C8 C10 C5 109.4(4) . . ?
C8 C10 H10A 109.8 . . ?
C8 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 P1 119.8(3) . . ?
C16 C11 P1 122.7(3) . . ?
C16 C11 C12 117.5(4) . . ?
O2 C12 C11 123.2(4) . . ?
O2 C12 C13 117.3(4) . . ?
C13 C12 C11 119.5(5) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.0(4) . . ?
C12 C13 Br1A 109.2(5) . . ?
C14 C13 H13 119.5 . . ?
C14 C13 Br1A 129.7(5) . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.8(4) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 116.9(5) . . ?
C14 C15 C17 121.3(5) . . ?
C16 C15 C17 121.8(4) . . ?
C11 C16 H16 118.4 . . ?
C15 C16 C11 123.2(4) . . ?
C15 C16 H16 118.4 . . ?
C15 C17 H17 105.6 . . ?
C18 C17 C15 111.9(4) . . ?
C18 C17 H17 105.6 . . ?
C19 C17 C15 113.3(5) . . ?
C19 C17 H17 105.6 . . ?
C19 C17 C18 114.0(7) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 P1 119.5(3) . . ?
C21 C20 C25 118.6(3) . . ?
C25 C20 P1 121.9(3) . . ?
O3 C21 C20 123.8(3) . . ?
O3 C21 C22 118.2(3) . . ?
C20 C21 C22 118.0(3) . . ?
C21 C22 H22 119.0 . . ?
C21 C22 Br1 118.3(3) . . ?
C23 C22 C21 122.0(3) . . ?
C23 C22 H22 119.0 . . ?
C23 C22 Br1 119.7(3) . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.4(3) . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C26 120.5(3) . . ?
C25 C24 C23 117.1(3) . . ?
C25 C24 C26 122.4(3) . . ?
C20 C25 H25 118.6 . . ?
C24 C25 C20 122.8(3) . . ?
C24 C25 H25 118.6 . . ?
C24 C26 H26 107.4 . . ?
C27 C26 C24 111.1(4) . . ?
C27 C26 H26 107.4 . . ?
C28 C26 C24 111.1(4) . . ?
C28 C26 H26 107.4 . . ?
C28 C26 C27 112.3(7) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
P1 C1 C2 C3 174.9(3) . . . . ?
P1 C1 C6 C5 -175.7(3) . . . . ?
P1 C1 C7 C8 -178.3(3) . . . . ?
P1 C11 C12 O2 -2.8(6) . . . . ?
P1 C11 C12 C13 177.9(3) . . . . ?
P1 C11 C16 C15 -178.8(3) . . . . ?
P1 C20 C21 O3 -0.2(5) . . . . ?
P1 C20 C21 C22 -179.6(3) . . . . ?
P1 C20 C25 C24 178.3(3) . . . . ?
O1 P1 C1 C2 -74.6(3) . . . . ?
O1 P1 C1 C6 42.0(3) . . . . ?
O1 P1 C1 C7 162.6(3) . . . . ?
O1 P1 C11 C12 -3.7(4) . . . . ?
O1 P1 C11 C16 174.7(3) . . . . ?
O1 P1 C20 C21 -18.9(3) . . . . ?
O1 P1 C20 C25 161.1(3) . . . . ?
O2 C12 C13 C14 -178.5(4) . . . . ?
O2 C12 C13 Br1A 0.6(6) . . . . ?
O3 C21 C22 C23 -178.5(4) . . . . ?
O3 C21 C22 Br1 0.1(5) . . . . ?
C1 P1 C11 C12 -124.7(3) . . . . ?
C1 P1 C11 C16 53.7(3) . . . . ?
C1 P1 C20 C21 100.2(3) . . . . ?
C1 P1 C20 C25 -79.8(3) . . . . ?
C1 C2 C3 C4 -60.6(5) . . . . ?
C1 C2 C3 C9 60.4(5) . . . . ?
C1 C7 C8 C9 -60.7(5) . . . . ?
C1 C7 C8 C10 59.8(5) . . . . ?
C2 C1 C6 C5 -58.6(5) . . . . ?
C2 C1 C7 C8 59.0(5) . . . . ?
C2 C3 C4 C5 60.1(5) . . . . ?
C2 C3 C9 C8 -61.6(5) . . . . ?
C3 C4 C5 C6 -59.3(5) . . . . ?
C3 C4 C5 C10 60.6(5) . . . . ?
C4 C3 C9 C8 59.9(5) . . . . ?
C4 C5 C6 C1 59.4(5) . . . . ?
C4 C5 C10 C8 -60.4(5) . . . . ?
C6 C1 C2 C3 59.2(4) . . . . ?
C6 C1 C7 C8 -58.8(4) . . . . ?
C6 C5 C10 C8 60.5(5) . . . . ?
C7 C1 C2 C3 -58.9(5) . . . . ?
C7 C1 C6 C5 59.8(4) . . . . ?
C7 C8 C9 C3 61.5(5) . . . . ?
C7 C8 C10 C5 -60.4(5) . . . . ?
C9 C3 C4 C5 -60.9(5) . . . . ?
C9 C8 C10 C5 60.1(5) . . . . ?
C10 C5 C6 C1 -60.6(5) . . . . ?
C10 C8 C9 C3 -59.6(5) . . . . ?
C11 P1 C1 C2 46.3(3) . . . . ?
C11 P1 C1 C6 162.8(2) . . . . ?
C11 P1 C1 C7 -76.5(3) . . . . ?
C11 P1 C20 C21 -138.6(3) . . . . ?
C11 P1 C20 C25 41.4(4) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
C11 C12 C13 Br1A -180.0(4) . . . . ?
C12 C11 C16 C15 -0.4(6) . . . . ?
C12 C13 C14 C15 -0.1(7) . . . . ?
C13 C14 C15 C16 -0.9(7) . . . . ?
C13 C14 C15 C17 -178.2(4) . . . . ?
C14 C15 C16 C11 1.1(6) . . . . ?
C14 C15 C17 C18 97.6(6) . . . . ?
C14 C15 C17 C19 -131.9(6) . . . . ?
C16 C11 C12 O2 178.8(4) . . . . ?
C16 C11 C12 C13 -0.6(6) . . . . ?
C16 C15 C17 C18 -79.6(6) . . . . ?
C16 C15 C17 C19 51.0(7) . . . . ?
C17 C15 C16 C11 178.4(4) . . . . ?
C20 P1 C1 C2 167.5(3) . . . . ?
C20 P1 C1 C6 -76.0(3) . . . . ?
C20 P1 C1 C7 44.7(3) . . . . ?
C20 P1 C11 C12 114.9(3) . . . . ?
C20 P1 C11 C16 -66.7(4) . . . . ?
C20 C21 C22 C23 1.0(6) . . . . ?
C20 C21 C22 Br1 179.6(3) . . . . ?
C21 C20 C25 C24 -1.7(6) . . . . ?
C21 C22 C23 C24 -1.2(6) . . . . ?
C22 C23 C24 C25 -0.1(6) . . . . ?
C22 C23 C24 C26 179.0(4) . . . . ?
C23 C24 C25 C20 1.6(6) . . . . ?
C23 C24 C26 C27 -122.6(6) . . . . ?
C23 C24 C26 C28 111.7(6) . . . . ?
C25 C20 C21 O3 179.8(4) . . . . ?
C25 C20 C21 C22 0.3(5) . . . . ?
C25 C24 C26 C27 56.5(7) . . . . ?
C25 C24 C26 C28 -69.3(7) . . . . ?
C26 C24 C25 C20 -177.5(4) . . . . ?
Br1 C22 C23 C24 -179.7(3) . . . . ?
Br1A C13 C14 C15 -179.1(4) . . . . ?

_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 1.724
_oxdiff_exptl_absorpt_empirical_full_min 0.738
