# Electronic Supplementary Material (ESI) for RSC Chemical Biology.
# 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).
# 
# 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_fg867m
_database_code_depnum_ccdc_archive 'CCDC 2078443'
loop_
_audit_author_name
_audit_author_address
'How Chee Ong'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-04-19 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_chemical_name_systematic        'pentyltri(p-tolyl)phosphonium bromide'
_chemical_name_common            ?
_chemical_formula_moiety         'C26 H32 Br P'
_chemical_formula_sum            'C26 H32 Br P'
_chemical_formula_iupac          ?
_chemical_formula_weight         455.39

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.9878(3)
_cell_length_b                   12.2294(3)
_cell_length_c                   17.2004(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.035(2)
_cell_angle_gamma                90
_cell_volume                     2311.29(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4156
_cell_measurement_theta_min      2.3682
_cell_measurement_theta_max      27.0751
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952

_exptl_absorpt_coefficient_mu    1.857
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.90

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            27688
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_full        30.49
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_reflns_number_total             7004
_reflns_number_gt                4193
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1110
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         7004
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²+1.6320P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.625
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.42358(3) 0.17307(3) 0.44920(2) 0.02673(10) Uani d . . . 1 . .
C C1 0.3365(3) 0.4754(2) 0.13276(18) 0.0219(6) Uani d . . . 1 . .
H H1A 0.384045 0.543995 0.135766 0.026 Uiso calc U . R 1 . .
H H1B 0.350439 0.442297 0.080986 0.026 Uiso calc U . R 1 . .
C C2 0.2012(3) 0.5006(2) 0.14285(18) 0.0227(7) Uani d . . . 1 . .
H H2A 0.188309 0.534065 0.194614 0.027 Uiso calc U . R 1 . .
H H2B 0.154711 0.431343 0.14117 0.027 Uiso calc U . R 1 . .
C C3 0.1518(3) 0.5782(2) 0.08019(19) 0.0243(7) Uani d . . . 1 . .
H H3A 0.200437 0.646269 0.079883 0.029 Uiso calc U . R 1 . .
H H3B 0.159802 0.543249 0.028518 0.029 Uiso calc U . R 1 . .
C C4 0.0187(3) 0.6059(3) 0.0950(2) 0.0277(7) Uani d . . . 1 . .
H H4A 0.011444 0.638388 0.147507 0.033 Uiso calc U . R 1 . .
H H4B -0.029097 0.537234 0.094728 0.033 Uiso calc U . R 1 . .
C C5 -0.0374(3) 0.6851(3) 0.0358(2) 0.0374(9) Uani d . . . 1 . .
H H5A 0.008503 0.753791 0.035911 0.056 Uiso calc U . R 1 . .
H H5B -0.122298 0.699691 0.049828 0.056 Uiso calc U . R 1 . .
H H5C -0.034255 0.652384 -0.016183 0.056 Uiso calc U . R 1 . .
C C6 0.5450(3) 0.3483(2) 0.19707(18) 0.0203(6) Uani d . . . 1 . .
C C7 0.6103(3) 0.3734(2) 0.13083(19) 0.0244(7) Uani d . . . 1 . .
H H7 0.574416 0.415152 0.090304 0.029 Uiso calc U . R 1 . .
C C8 0.7287(3) 0.3366(3) 0.12461(19) 0.0269(7) Uani d . . . 1 . .
H H8 0.773642 0.353397 0.078987 0.032 Uiso calc U . R 1 . .
C C9 0.7843(3) 0.2757(2) 0.18311(19) 0.0234(7) Uani d . . . 1 . .
C C10 0.9128(3) 0.2360(3) 0.1741(2) 0.0312(8) Uani d . . . 1 . .
H H10A 0.935648 0.19238 0.219603 0.047 Uiso calc U . R 1 . .
H H10B 0.967681 0.298872 0.169565 0.047 Uiso calc U . R 1 . .
H H10C 0.919068 0.190873 0.127167 0.047 Uiso calc U . R 1 . .
C C11 0.7170(3) 0.2537(2) 0.24979(19) 0.0244(7) Uani d . . . 1 . .
H H11 0.753684 0.213868 0.291017 0.029 Uiso calc U . R 1 . .
C C12 0.5980(3) 0.2887(2) 0.25736(19) 0.0236(7) Uani d . . . 1 . .
H H12 0.552954 0.272428 0.303022 0.028 Uiso calc U . R 1 . .
C C13 0.2990(3) 0.2594(2) 0.19832(18) 0.0202(6) Uani d . . . 1 . .
C C14 0.2566(3) 0.2275(2) 0.12514(18) 0.0197(6) Uani d . . . 1 . .
H H14 0.272657 0.271586 0.080855 0.024 Uiso calc U . R 1 . .
C C15 0.1913(3) 0.1320(2) 0.11740(19) 0.0225(7) Uani d . . . 1 . .
H H15 0.161756 0.111326 0.067599 0.027 Uiso calc U . R 1 . .
C C16 0.1677(3) 0.0648(2) 0.18131(19) 0.0219(7) Uani d . . . 1 . .
C C17 0.0911(3) -0.0361(3) 0.1726(2) 0.0319(8) Uani d . . . 1 . .
H H17A 0.047156 -0.033215 0.12305 0.048 Uiso calc U . R 1 . .
H H17B 0.032619 -0.040053 0.215492 0.048 Uiso calc U . R 1 . .
H H17C 0.143563 -0.100903 0.173561 0.048 Uiso calc U . R 1 . .
C C18 0.2158(3) 0.0946(2) 0.25324(19) 0.0233(7) Uani d . . . 1 . .
H H18 0.204018 0.047934 0.296762 0.028 Uiso calc U . R 1 . .
C C19 0.2806(3) 0.1911(2) 0.26248(18) 0.0226(7) Uani d . . . 1 . .
H H19 0.312278 0.210619 0.311981 0.027 Uiso calc U . R 1 . .
C C20 0.3651(3) 0.4450(2) 0.30011(17) 0.0194(6) Uani d . . . 1 . .
C C21 0.2568(3) 0.4353(2) 0.34131(19) 0.0225(7) Uani d . . . 1 . .
H H21 0.193387 0.389991 0.322013 0.027 Uiso calc U . R 1 . .
C C22 0.2412(3) 0.4914(2) 0.41003(18) 0.0230(7) Uani d . . . 1 . .
H H22 0.166604 0.483959 0.437383 0.028 Uiso calc U . R 1 . .
C C23 0.3322(3) 0.5590(2) 0.44083(18) 0.0230(7) Uani d . . . 1 . .
C C24 0.3141(3) 0.6187(3) 0.51628(19) 0.0288(7) Uani d . . . 1 . .
H H24A 0.326733 0.568066 0.559714 0.043 Uiso calc U . R 1 . .
H H24B 0.231147 0.647938 0.51841 0.043 Uiso calc U . R 1 . .
H H24C 0.372632 0.678924 0.51993 0.043 Uiso calc U . R 1 . .
C C25 0.4394(3) 0.5689(2) 0.39907(19) 0.0239(7) Uani d . . . 1 . .
H H25 0.502446 0.61463 0.418334 0.029 Uiso calc U . R 1 . .
C C26 0.4564(3) 0.5133(2) 0.32974(19) 0.0240(7) Uani d . . . 1 . .
H H26 0.530631 0.521542 0.302055 0.029 Uiso calc U . R 1 . .
P P1 0.38666(7) 0.38284(6) 0.20706(5) 0.01978(17) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.528(4) ?
C1 P1 . 1.793(3) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.535(4) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.523(4) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.534(4) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 C7 . 1.381(4) ?
C6 C12 . 1.394(4) ?
C6 P1 . 1.799(3) ?
C7 C8 . 1.380(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.393(4) ?
C8 H8 . 0.95 ?
C9 C11 . 1.391(4) ?
C9 C10 . 1.501(4) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.382(4) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 C14 . 1.398(4) ?
C13 C19 . 1.399(4) ?
C13 P1 . 1.797(3) ?
C14 C15 . 1.377(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.397(4) ?
C15 H15 . 0.95 ?
C16 C18 . 1.394(4) ?
C16 C17 . 1.501(4) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 C19 . 1.388(4) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
C20 C21 . 1.391(4) ?
C20 C26 . 1.401(4) ?
C20 P1 . 1.788(3) ?
C21 C22 . 1.377(4) ?
C21 H21 . 0.95 ?
C22 C23 . 1.401(4) ?
C22 H22 . 0.95 ?
C23 C25 . 1.385(4) ?
C23 C24 . 1.502(4) ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 C26 . 1.385(4) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 P1 . . 110.2(2) ?
C2 C1 H1A . . 109.6 ?
P1 C1 H1A . . 109.6 ?
C2 C1 H1B . . 109.6 ?
P1 C1 H1B . . 109.6 ?
H1A C1 H1B . . 108.1 ?
C1 C2 C3 . . 112.9(3) ?
C1 C2 H2A . . 109.0 ?
C3 C2 H2A . . 109.0 ?
C1 C2 H2B . . 109.0 ?
C3 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
C4 C3 C2 . . 111.1(3) ?
C4 C3 H3A . . 109.4 ?
C2 C3 H3A . . 109.4 ?
C4 C3 H3B . . 109.4 ?
C2 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C3 C4 C5 . . 114.5(3) ?
C3 C4 H4A . . 108.6 ?
C5 C4 H4A . . 108.6 ?
C3 C4 H4B . . 108.6 ?
C5 C4 H4B . . 108.6 ?
H4A C4 H4B . . 107.6 ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C7 C6 C12 . . 120.8(3) ?
C7 C6 P1 . . 122.0(2) ?
C12 C6 P1 . . 117.1(2) ?
C8 C7 C6 . . 118.8(3) ?
C8 C7 H7 . . 120.6 ?
C6 C7 H7 . . 120.6 ?
C7 C8 C9 . . 122.1(3) ?
C7 C8 H8 . . 119.0 ?
C9 C8 H8 . . 119.0 ?
C11 C9 C8 . . 117.8(3) ?
C11 C9 C10 . . 121.6(3) ?
C8 C9 C10 . . 120.7(3) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C12 C11 C9 . . 121.4(3) ?
C12 C11 H11 . . 119.3 ?
C9 C11 H11 . . 119.3 ?
C11 C12 C6 . . 119.1(3) ?
C11 C12 H12 . . 120.4 ?
C6 C12 H12 . . 120.4 ?
C14 C13 C19 . . 119.7(3) ?
C14 C13 P1 . . 119.2(2) ?
C19 C13 P1 . . 120.9(2) ?
C15 C14 C13 . . 119.8(3) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C14 C15 C16 . . 121.3(3) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C18 C16 C15 . . 118.3(3) ?
C18 C16 C17 . . 121.1(3) ?
C15 C16 C17 . . 120.6(3) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C19 C18 C16 . . 121.2(3) ?
C19 C18 H18 . . 119.4 ?
C16 C18 H18 . . 119.4 ?
C18 C19 C13 . . 119.5(3) ?
C18 C19 H19 . . 120.3 ?
C13 C19 H19 . . 120.3 ?
C21 C20 C26 . . 118.6(3) ?
C21 C20 P1 . . 122.3(2) ?
C26 C20 P1 . . 118.9(2) ?
C22 C21 C20 . . 120.1(3) ?
C22 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
C21 C22 C23 . . 122.0(3) ?
C21 C22 H22 . . 119.0 ?
C23 C22 H22 . . 119.0 ?
C25 C23 C22 . . 117.5(3) ?
C25 C23 C24 . . 121.3(3) ?
C22 C23 C24 . . 121.2(3) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C23 C25 C26 . . 121.3(3) ?
C23 C25 H25 . . 119.4 ?
C26 C25 H25 . . 119.4 ?
C25 C26 C20 . . 120.6(3) ?
C25 C26 H26 . . 119.7 ?
C20 C26 H26 . . 119.7 ?
C20 P1 C1 . . 109.20(14) ?
C20 P1 C13 . . 111.16(14) ?
C1 P1 C13 . . 107.82(14) ?
C20 P1 C6 . . 108.31(14) ?
C1 P1 C6 . . 112.15(14) ?
C13 P1 C6 . . 108.22(13) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile, diethyl ether'
####################################################################### 
# 
# 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_fg1132_ohc
_database_code_depnum_ccdc_archive 'CCDC 2078444'
loop_
_audit_author_name
_audit_author_address
'How Chee Ong'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-04-19 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_chemical_name_systematic        
'pentyltris(3,5-dimethylphenyl)phosphonium bromide'
_chemical_name_common            ?
_chemical_formula_moiety         'C29 H38 Br P'
_chemical_formula_sum            'C29 H38 Br P'
_chemical_formula_iupac          ?
_chemical_formula_weight         497.47

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   17.4833(10)
_cell_length_b                   14.5439(9)
_cell_length_c                   20.9956(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.798(2)
_cell_angle_gamma                90
_cell_volume                     5244.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5274
_cell_measurement_theta_min      2.1864
_cell_measurement_theta_max      23.9893
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2096

_exptl_absorpt_coefficient_mu    1.643
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.85

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker X8 Apex'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            32456
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             4644
_reflns_number_gt                3274
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0835
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_number_reflns         4644
_refine_ls_number_parameters     288
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0258P)²+11.0579P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.522
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.5 0.97439(3) 0.75 0.02264(12) Uani d T P S 1 . .
Br Br2 0.5 0.53174(3) 0.75 0.03081(14) Uani d T P S 1 . .
P P1 0.58278(4) 0.75666(5) 0.60161(3) 0.01359(16) Uani d . . . 1 . .
C C1 0.67423(16) 0.78818(19) 0.65190(13) 0.0166(6) Uani d . . . 1 . .
C C2 0.67727(17) 0.86765(19) 0.68972(13) 0.0188(6) Uani d . . . 1 . .
H H2 0.630882 0.900737 0.691564 0.023 Uiso calc U . R 1 . .
C C3 0.74813(17) 0.8982(2) 0.72463(13) 0.0216(7) Uani d . . . 1 . .
C C4 0.81491(18) 0.8478(2) 0.72131(14) 0.0245(7) Uani d . . . 1 . .
H H4 0.863622 0.869229 0.744396 0.029 Uiso calc U . R 1 . .
C C5 0.81292(17) 0.7671(2) 0.68537(14) 0.0237(7) Uani d . . . 1 . .
C C6 0.74157(16) 0.73792(19) 0.65010(13) 0.0198(6) Uani d . . . 1 . .
H H6 0.738825 0.683532 0.624723 0.024 Uiso calc U . R 1 . .
C C7 0.88686(18) 0.7142(3) 0.68284(18) 0.0396(9) Uani d . . . 1 . .
H H7A 0.887752 0.696735 0.63791 0.059 Uiso calc U . R 1 . .
H H7B 0.888607 0.658753 0.709578 0.059 Uiso calc U . R 1 . .
H H7C 0.932094 0.752941 0.699403 0.059 Uiso calc U . R 1 . .
C C8 0.7521(2) 0.9858(2) 0.76406(15) 0.0348(9) Uani d . . . 1 . .
H H8A 0.793796 1.025092 0.754069 0.052 Uiso calc U . R 1 . .
H H8B 0.762729 0.970556 0.810353 0.052 Uiso calc U . R 1 . .
H H8C 0.702265 1.018358 0.753303 0.052 Uiso calc U . R 1 . .
C C9 0.59009(16) 0.64471(18) 0.56761(13) 0.0153(6) Uani d . . . 1 . .
C C10 0.57418(15) 0.56707(18) 0.60180(13) 0.0154(6) Uani d . . . 1 . .
H H10 0.557728 0.573811 0.642183 0.018 Uiso calc U . R 1 . .
C C11 0.58238(16) 0.47939(19) 0.57683(13) 0.0167(6) Uani d . . . 1 . .
C C12 0.60659(16) 0.47211(19) 0.51771(13) 0.0181(6) Uani d . . . 1 . .
H H12 0.612205 0.412577 0.500541 0.022 Uiso calc U . R 1 . .
C C13 0.62299(17) 0.5485(2) 0.48253(14) 0.0197(7) Uani d . . . 1 . .
C C14 0.61440(16) 0.63544(19) 0.50809(13) 0.0173(6) Uani d . . . 1 . .
H H14 0.625075 0.688676 0.485039 0.021 Uiso calc U . R 1 . .
C C15 0.64680(19) 0.5378(2) 0.41732(14) 0.0296(8) Uani d . . . 1 . .
H H15A 0.600985 0.522373 0.384475 0.044 Uiso calc U . R 1 . .
H H15B 0.685451 0.488504 0.419697 0.044 Uiso calc U . R 1 . .
H H15C 0.669399 0.595572 0.405502 0.044 Uiso calc U . R 1 . .
C C16 0.56482(18) 0.39549(19) 0.61334(14) 0.0225(7) Uani d . . . 1 . .
H H16A 0.531727 0.353553 0.583644 0.034 Uiso calc U . R 1 . .
H H16B 0.537697 0.413811 0.648165 0.034 Uiso calc U . R 1 . .
H H16C 0.613603 0.36439 0.632028 0.034 Uiso calc U . R 1 . .
C C17 0.56344(16) 0.83684(18) 0.53497(13) 0.0158(6) Uani d . . . 1 . .
C C18 0.49610(16) 0.82796(19) 0.48693(13) 0.0175(6) Uani d . . . 1 . .
H H18 0.458501 0.782526 0.491592 0.021 Uiso calc U . R 1 . .
C C19 0.48383(16) 0.88425(18) 0.43315(13) 0.0171(6) Uani d . . . 1 . .
C C20 0.53994(17) 0.95064(19) 0.42708(13) 0.0188(6) Uani d . . . 1 . .
H H20 0.53152 0.990271 0.390464 0.023 Uiso calc U . R 1 . .
C C21 0.60732(17) 0.96003(19) 0.47304(14) 0.0207(7) Uani d . . . 1 . .
C C22 0.61847(16) 0.90307(19) 0.52737(14) 0.0183(7) Uani d . . . 1 . .
H H22 0.66417 0.909533 0.559598 0.022 Uiso calc U . R 1 . .
C C23 0.66729(19) 1.0298(2) 0.46363(17) 0.0365(9) Uani d . . . 1 . .
H H23A 0.717162 0.998911 0.463838 0.055 Uiso calc U . R 1 . .
H H23B 0.673344 1.074919 0.498871 0.055 Uiso calc U . R 1 . .
H H23C 0.650585 1.061115 0.422028 0.055 Uiso calc U . R 1 . .
C C24 0.41260(18) 0.8765(2) 0.38038(14) 0.0288(8) Uani d . . . 1 . .
H H24A 0.422989 0.905436 0.340707 0.043 Uiso calc U . R 1 . .
H H24B 0.36869 0.907541 0.394164 0.043 Uiso calc U . R 1 . .
H H24C 0.399846 0.81148 0.371961 0.043 Uiso calc U . R 1 . .
C C25 0.51042(15) 0.75803(19) 0.65219(12) 0.0160(6) Uani d . . . 1 . .
H H25A 0.526812 0.713847 0.688016 0.019 Uiso calc U . R 1 . .
H H25B 0.510805 0.819933 0.671867 0.019 Uiso calc U . R 1 . .
C C26 0.42641(16) 0.73546(19) 0.62083(13) 0.0200(7) Uani d . . . 1 . .
H H26A 0.408359 0.779055 0.584943 0.024 Uiso calc U . R 1 . .
H H26B 0.423976 0.672617 0.602442 0.024 Uiso calc U . R 1 . .
C C27 0.37309(16) 0.7417(2) 0.67049(14) 0.0248(7) Uani d . . . 1 . .
H H27A 0.394436 0.701806 0.707831 0.03 Uiso calc U . R 1 . .
H H27B 0.3738 0.805687 0.686592 0.03 Uiso calc U . R 1 . .
C C28 0.28908(17) 0.7139(2) 0.64511(15) 0.0269(7) Uani d . . . 1 . .
H H28A 0.287948 0.649075 0.630688 0.032 Uiso calc U . R 1 . .
H H28B 0.259731 0.717825 0.681029 0.032 Uiso calc U . R 1 . .
C C29 0.2488(2) 0.7724(3) 0.58971(19) 0.0511(11) Uani d . . . 1 . .
H H29A 0.277004 0.768315 0.553614 0.077 Uiso calc U . R 1 . .
H H29B 0.247955 0.836521 0.603972 0.077 Uiso calc U . R 1 . .
H H29C 0.195351 0.750545 0.57548 0.077 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C9 . 1.792(3) ?
P1 C25 . 1.798(3) ?
P1 C1 . 1.802(3) ?
P1 C17 . 1.804(3) ?
C1 C6 . 1.392(4) ?
C1 C2 . 1.398(4) ?
C2 C3 . 1.389(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.392(4) ?
C3 C8 . 1.513(4) ?
C4 C5 . 1.392(4) ?
C4 H4 . 0.95 ?
C5 C6 . 1.392(4) ?
C5 C7 . 1.514(4) ?
C6 H6 . 0.95 ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 C10 . 1.394(4) ?
C9 C14 . 1.400(4) ?
C10 C11 . 1.396(4) ?
C10 H10 . 0.95 ?
C11 C12 . 1.388(4) ?
C11 C16 . 1.503(4) ?
C12 C13 . 1.393(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.393(4) ?
C13 C15 . 1.512(4) ?
C14 H14 . 0.95 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 C22 . 1.391(4) ?
C17 C18 . 1.405(4) ?
C18 C19 . 1.379(4) ?
C18 H18 . 0.95 ?
C19 C20 . 1.399(4) ?
C19 C24 . 1.508(4) ?
C20 C21 . 1.383(4) ?
C20 H20 . 0.95 ?
C21 C22 . 1.394(4) ?
C21 C23 . 1.498(4) ?
C22 H22 . 0.95 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 C26 . 1.528(4) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C26 C27 . 1.526(4) ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C27 C28 . 1.520(4) ?
C27 H27A . 0.99 ?
C27 H27B . 0.99 ?
C28 C29 . 1.505(5) ?
C28 H28A . 0.99 ?
C28 H28B . 0.99 ?
C29 H29A . 0.98 ?
C29 H29B . 0.98 ?
C29 H29C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 P1 C25 . . 110.85(13) ?
C9 P1 C1 . . 110.04(13) ?
C25 P1 C1 . . 107.23(12) ?
C9 P1 C17 . . 107.19(13) ?
C25 P1 C17 . . 113.61(13) ?
C1 P1 C17 . . 107.86(13) ?
C6 C1 C2 . . 120.5(3) ?
C6 C1 P1 . . 120.8(2) ?
C2 C1 P1 . . 118.6(2) ?
C3 C2 C1 . . 120.0(3) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C2 C3 C4 . . 118.6(3) ?
C2 C3 C8 . . 120.2(3) ?
C4 C3 C8 . . 121.2(3) ?
C3 C4 C5 . . 122.4(3) ?
C3 C4 H4 . . 118.8 ?
C5 C4 H4 . . 118.8 ?
C6 C5 C4 . . 118.3(3) ?
C6 C5 C7 . . 120.8(3) ?
C4 C5 C7 . . 120.8(3) ?
C5 C6 C1 . . 120.2(3) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
C5 C7 H7A . . 109.5 ?
C5 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C5 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C3 C8 H8A . . 109.5 ?
C3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C14 . . 120.3(2) ?
C10 C9 P1 . . 119.7(2) ?
C14 C9 P1 . . 120.0(2) ?
C9 C10 C11 . . 120.1(3) ?
C9 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
C12 C11 C10 . . 118.4(3) ?
C12 C11 C16 . . 121.3(3) ?
C10 C11 C16 . . 120.3(3) ?
C11 C12 C13 . . 122.7(3) ?
C11 C12 H12 . . 118.6 ?
C13 C12 H12 . . 118.6 ?
C14 C13 C12 . . 118.2(3) ?
C14 C13 C15 . . 120.7(3) ?
C12 C13 C15 . . 121.1(3) ?
C13 C14 C9 . . 120.3(3) ?
C13 C14 H14 . . 119.9 ?
C9 C14 H14 . . 119.9 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C11 C16 H16A . . 109.5 ?
C11 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C11 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C22 C17 C18 . . 119.0(3) ?
C22 C17 P1 . . 120.2(2) ?
C18 C17 P1 . . 120.5(2) ?
C19 C18 C17 . . 120.9(3) ?
C19 C18 H18 . . 119.5 ?
C17 C18 H18 . . 119.5 ?
C18 C19 C20 . . 118.7(3) ?
C18 C19 C24 . . 122.5(3) ?
C20 C19 C24 . . 118.8(2) ?
C21 C20 C19 . . 121.7(3) ?
C21 C20 H20 . . 119.2 ?
C19 C20 H20 . . 119.2 ?
C20 C21 C22 . . 118.9(3) ?
C20 C21 C23 . . 120.0(3) ?
C22 C21 C23 . . 121.1(3) ?
C17 C22 C21 . . 120.8(3) ?
C17 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
C21 C23 H23A . . 109.5 ?
C21 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C21 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C19 C24 H24A . . 109.5 ?
C19 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C19 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C26 C25 P1 . . 117.96(18) ?
C26 C25 H25A . . 107.8 ?
P1 C25 H25A . . 107.8 ?
C26 C25 H25B . . 107.8 ?
P1 C25 H25B . . 107.8 ?
H25A C25 H25B . . 107.2 ?
C27 C26 C25 . . 110.7(2) ?
C27 C26 H26A . . 109.5 ?
C25 C26 H26A . . 109.5 ?
C27 C26 H26B . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 108.1 ?
C28 C27 C26 . . 114.7(2) ?
C28 C27 H27A . . 108.6 ?
C26 C27 H27A . . 108.6 ?
C28 C27 H27B . . 108.6 ?
C26 C27 H27B . . 108.6 ?
H27A C27 H27B . . 107.6 ?
C29 C28 C27 . . 113.7(3) ?
C29 C28 H28A . . 108.8 ?
C27 C28 H28A . . 108.8 ?
C29 C28 H28B . . 108.8 ?
C27 C28 H28B . . 108.8 ?
H28A C28 H28B . . 107.7 ?
C28 C29 H29A . . 109.5 ?
C28 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C28 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile, diethyl ether'
