# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 2095086'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT434_1                   
;
PROBLEM: Short Inter HL..HL Contact Br2C     ..Br22             3.21 Ang.  
RESPONSE: This reflects halogen...halogen interactions.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        '(dibromomethyl)(triphenyl)phosphanium bromide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 Br3 P'
_chemical_formula_weight         515.02

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'
Br Br -0.6763 1.2805 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   17.7546(4)
_cell_length_b                   15.5320(3)
_cell_length_c                   28.3321(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.2280(10)
_cell_angle_gamma                90
_cell_volume                     7711.9(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    6372
_cell_measurement_theta_min      3.160
_cell_measurement_theta_max      72.294

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             4000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    8.506
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5887
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67258
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.160
_diffrn_reflns_theta_max         72.294
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7620
_reflns_number_gt                6372
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+15.9340P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7620
_refine_ls_number_parameters     415
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0878
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1A P 0.56794(5) 0.22515(5) 0.57403(3) 0.02324(17) Uani 1 1 d . . . . .
C2A C 0.5260(2) 0.1695(2) 0.52077(12) 0.0252(7) Uani 1 1 d . . . . .
C3A C 0.5708(2) 0.1230(2) 0.49383(13) 0.0304(7) Uani 1 1 d . . . . .
H3A H 0.624866 0.124493 0.501529 0.036 Uiso 1 1 calc R U . . .
Br2C Br 0.81613(2) 0.40793(2) 0.71692(2) 0.03356(10) Uani 1 1 d . . . . .
C2B C 0.2861(2) 0.3530(2) 0.37956(13) 0.0287(7) Uani 1 1 d . . . . .
C4A C 0.5354(3) 0.0744(2) 0.45553(14) 0.0365(9) Uani 1 1 d . . . . .
H4A H 0.565751 0.043125 0.436736 0.044 Uiso 1 1 calc R U . . .
Br3C Br 0.15807(2) 0.25177(3) 0.28784(2) 0.04525(12) Uani 1 1 d . . . . .
C3B C 0.2389(2) 0.4239(2) 0.36775(15) 0.0349(8) Uani 1 1 d . . . . .
H3B H 0.226084 0.441578 0.335365 0.042 Uiso 1 1 calc R U . . .
C5A C 0.4572(3) 0.0706(3) 0.44423(15) 0.0405(10) Uani 1 1 d . . . . .
H5A H 0.433911 0.037305 0.417717 0.049 Uiso 1 1 calc R U . . .
Br4C Br 0.25586(2) 0.12511(3) 0.36348(2) 0.03558(10) Uani 1 1 d . . . . .
C4B C 0.2106(3) 0.4684(3) 0.40350(17) 0.0420(10) Uani 1 1 d . . . . .
H4B H 0.178113 0.516723 0.395722 0.050 Uiso 1 1 calc R U . . .
C6A C 0.4126(2) 0.1154(3) 0.47165(14) 0.0372(9) Uani 1 1 d . . . . .
H6A H 0.358589 0.111995 0.464290 0.045 Uiso 1 1 calc R U . . .
C5B C 0.2298(3) 0.4424(3) 0.45047(17) 0.0470(11) Uani 1 1 d . . . . .
H5B H 0.211470 0.473927 0.475007 0.056 Uiso 1 1 calc R U . . .
C7A C 0.4461(2) 0.1651(2) 0.50961(14) 0.0327(8) Uani 1 1 d . . . . .
H7A H 0.415300 0.196334 0.528142 0.039 Uiso 1 1 calc R U . . .
C6B C 0.2752(3) 0.3713(3) 0.46223(15) 0.0484(11) Uani 1 1 d . . . . .
H6B H 0.286714 0.353225 0.494622 0.058 Uiso 1 1 calc R U . . .
C8A C 0.5176(2) 0.3224(2) 0.58149(15) 0.0323(8) Uani 1 1 d . U . . .
C7B C 0.3042(3) 0.3257(3) 0.42695(14) 0.0389(9) Uani 1 1 d . . . . .
H7B H 0.335799 0.276773 0.434953 0.047 Uiso 1 1 calc R U . . .
C9A C 0.4830(2) 0.3691(3) 0.54209(18) 0.0435(10) Uani 1 1 d . U . . .
H9A H 0.482362 0.347939 0.510575 0.052 Uiso 1 1 calc R U . . .
C8B C 0.4160(2) 0.2562(2) 0.35211(13) 0.0298(7) Uani 1 1 d . U . . .
C10A C 0.4489(3) 0.4483(3) 0.5499(2) 0.0585(14) Uani 1 1 d . U . . .
H10A H 0.424444 0.481155 0.523540 0.070 Uiso 1 1 calc R U . . .
C9B C 0.4664(2) 0.3010(3) 0.38634(15) 0.0382(9) Uani 1 1 d . U . . .
H9B H 0.448403 0.346513 0.404001 0.046 Uiso 1 1 calc R U . . .
C11A C 0.4511(3) 0.4784(3) 0.5962(2) 0.0642(16) Uani 1 1 d . U . . .
H11A H 0.427377 0.531693 0.601204 0.077 Uiso 1 1 calc R U . . .
C10B C 0.5429(3) 0.2784(3) 0.39427(17) 0.0461(10) Uani 1 1 d . U . . .
H10B H 0.577589 0.307931 0.417805 0.055 Uiso 1 1 calc R U . . .
C12A C 0.4864(3) 0.4330(3) 0.6344(2) 0.0613(15) Uani 1 1 d . U . . .
H12A H 0.488555 0.455439 0.665795 0.074 Uiso 1 1 calc R U . . .
C11B C 0.5686(2) 0.2134(3) 0.36813(18) 0.0469(11) Uani 1 1 d . U . . .
H11B H 0.621160 0.198619 0.373460 0.056 Uiso 1 1 calc R U . . .
C13A C 0.5193(3) 0.3541(3) 0.62755(18) 0.0490(11) Uani 1 1 d . U . . .
H13A H 0.542901 0.321644 0.654290 0.059 Uiso 1 1 calc R U . . .
C12B C 0.5188(3) 0.1693(3) 0.33420(19) 0.0496(11) Uani 1 1 d . . . . .
H12B H 0.537221 0.124355 0.316353 0.060 Uiso 1 1 calc R U . . .
C14A C 0.5640(2) 0.1562(2) 0.62423(12) 0.0269(7) Uani 1 1 d . . . . .
C13B C 0.4428(2) 0.1901(3) 0.32618(16) 0.0393(9) Uani 1 1 d . . . . .
H13B H 0.408450 0.159392 0.302960 0.047 Uiso 1 1 calc R U . . .
C15A C 0.4934(2) 0.1414(3) 0.63875(16) 0.0432(10) Uani 1 1 d . . . . .
H15A H 0.449052 0.170063 0.623073 0.052 Uiso 1 1 calc R U . . .
C14B C 0.3285(2) 0.3659(2) 0.28271(13) 0.0310(8) Uani 1 1 d . . . . .
C16A C 0.4881(3) 0.0854(3) 0.67572(18) 0.0509(12) Uani 1 1 d . . . . .
H16A H 0.440117 0.075081 0.685453 0.061 Uiso 1 1 calc R U . . .
C15B C 0.3523(2) 0.4502(3) 0.29095(16) 0.0393(9) Uani 1 1 d . . . . .
H15B H 0.358976 0.473095 0.322432 0.047 Uiso 1 1 calc R U . . .
C17A C 0.5530(3) 0.0440(3) 0.69874(15) 0.0393(9) Uani 1 1 d . . . . .
H17A H 0.549262 0.005842 0.724473 0.047 Uiso 1 1 calc R U . . .
C16B C 0.3666(3) 0.5009(3) 0.25316(19) 0.0493(11) Uani 1 1 d . . . . .
H16B H 0.383506 0.558662 0.258411 0.059 Uiso 1 1 calc R U . . .
C18A C 0.6223(2) 0.0576(2) 0.68474(13) 0.0327(8) Uani 1 1 d . . . . .
H18A H 0.666378 0.028970 0.700776 0.039 Uiso 1 1 calc R U . . .
C17B C 0.3556(3) 0.4659(3) 0.20738(17) 0.0475(11) Uani 1 1 d . . . . .
H17B H 0.364578 0.500332 0.181127 0.057 Uiso 1 1 calc R U . . .
C19A C 0.6282(2) 0.1133(2) 0.64695(13) 0.0293(7) Uani 1 1 d . . . . .
H19A H 0.676127 0.121895 0.636800 0.035 Uiso 1 1 calc R U . . .
C18B C 0.3322(3) 0.3829(3) 0.19974(16) 0.0459(10) Uani 1 1 d . . . . .
H18B H 0.324876 0.360124 0.168219 0.055 Uiso 1 1 calc R U . . .
C20A C 0.6667(2) 0.2514(2) 0.57107(12) 0.0254(7) Uani 1 1 d . . . . .
H20A H 0.695335 0.196954 0.567592 0.030 Uiso 1 1 calc R U . . .
C20B C 0.2588(2) 0.2067(2) 0.31215(13) 0.0293(7) Uani 1 1 d . . . . .
H20B H 0.278913 0.176829 0.285488 0.035 Uiso 1 1 calc R U . . .
Br1C Br 0.73757(2) 0.44844(3) 0.43284(2) 0.03263(10) Uani 1 1 d . . . . .
C19B C 0.3192(3) 0.3325(3) 0.23663(15) 0.0406(9) Uani 1 1 d . . . . .
H19B H 0.303735 0.274350 0.230995 0.049 Uiso 1 1 calc R U . . .
Br22 Br 0.71330(2) 0.30982(2) 0.62954(2) 0.03002(9) Uani 1 1 d . . . . .
Br21 Br 0.67439(2) 0.32602(2) 0.51669(2) 0.03143(10) Uani 1 1 d . . . . .
P1B P 0.32186(5) 0.29689(6) 0.33267(3) 0.02603(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1A C8A 1.785(4) . ?
P1A C14A 1.791(4) . ?
P1A C2A 1.794(3) . ?
P1A C20A 1.816(4) . ?
C2A C3A 1.390(5) . ?
C2A C7A 1.404(5) . ?
C3A C4A 1.387(5) . ?
C2B C3B 1.392(5) . ?
C2B C7B 1.396(5) . ?
C2B P1B 1.788(4) . ?
C4A C5A 1.375(6) . ?
Br3C C20B 1.941(4) . ?
C3B C4B 1.386(6) . ?
C5A C6A 1.383(6) . ?
Br4C C20B 1.936(4) . ?
C4B C5B 1.380(7) . ?
C6A C7A 1.379(5) . ?
C5B C6B 1.376(7) . ?
C6B C7B 1.389(6) . ?
C8A C9A 1.389(6) . ?
C8A C13A 1.391(6) . ?
C9A C10A 1.403(6) . ?
C8B C13B 1.389(6) . ?
C8B C9B 1.395(5) . ?
C8B P1B 1.790(4) . ?
C10A C11A 1.386(9) . ?
C9B C10B 1.387(6) . ?
C11A C12A 1.359(9) . ?
C10B C11B 1.373(7) . ?
C12A C13A 1.384(6) . ?
C11B C12B 1.379(7) . ?
C12B C13B 1.371(6) . ?
C14A C19A 1.386(5) . ?
C14A C15A 1.400(5) . ?
C15A C16A 1.376(6) . ?
C14B C15B 1.384(6) . ?
C14B C19B 1.390(6) . ?
C14B P1B 1.794(4) . ?
C16A C17A 1.388(6) . ?
C15B C16B 1.385(6) . ?
C17A C18A 1.368(6) . ?
C16B C17B 1.391(7) . ?
C18A C19A 1.394(5) . ?
C17B C18B 1.361(7) . ?
C18B C19B 1.355(6) . ?
C20A Br21 1.950(3) . ?
C20A Br22 1.952(3) . ?
C20B P1B 1.830(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8A P1A C14A 109.19(18) . . ?
C8A P1A C2A 111.06(17) . . ?
C14A P1A C2A 108.41(16) . . ?
C8A P1A C20A 108.68(17) . . ?
C14A P1A C20A 109.41(16) . . ?
C2A P1A C20A 110.08(16) . . ?
C3A C2A C7A 119.9(3) . . ?
C3A C2A P1A 121.0(3) . . ?
C7A C2A P1A 118.7(3) . . ?
C4A C3A C2A 119.0(4) . . ?
C3B C2B C7B 120.6(3) . . ?
C3B C2B P1B 118.6(3) . . ?
C7B C2B P1B 120.8(3) . . ?
C5A C4A C3A 121.3(4) . . ?
C4B C3B C2B 119.6(4) . . ?
C4A C5A C6A 119.6(4) . . ?
C5B C4B C3B 119.7(4) . . ?
C7A C6A C5A 120.4(4) . . ?
C6B C5B C4B 120.9(4) . . ?
C6A C7A C2A 119.8(4) . . ?
C5B C6B C7B 120.3(4) . . ?
C9A C8A C13A 120.6(4) . . ?
C9A C8A P1A 120.8(3) . . ?
C13A C8A P1A 118.4(3) . . ?
C6B C7B C2B 118.9(4) . . ?
C8A C9A C10A 118.5(5) . . ?
C13B C8B C9B 120.1(4) . . ?
C13B C8B P1B 118.7(3) . . ?
C9B C8B P1B 120.0(3) . . ?
C11A C10A C9A 119.8(5) . . ?
C10B C9B C8B 119.2(4) . . ?
C12A C11A C10A 121.2(4) . . ?
C11B C10B C9B 120.0(4) . . ?
C11A C12A C13A 119.9(5) . . ?
C10B C11B C12B 120.7(4) . . ?
C12A C13A C8A 119.9(5) . . ?
C13B C12B C11B 120.1(4) . . ?
C19A C14A C15A 119.6(3) . . ?
C19A C14A P1A 121.5(3) . . ?
C15A C14A P1A 118.8(3) . . ?
C12B C13B C8B 119.8(4) . . ?
C16A C15A C14A 120.0(4) . . ?
C15B C14B C19B 119.9(4) . . ?
C15B C14B P1B 119.2(3) . . ?
C19B C14B P1B 120.4(3) . . ?
C15A C16A C17A 119.9(4) . . ?
C14B C15B C16B 119.8(4) . . ?
C18A C17A C16A 120.7(4) . . ?
C15B C16B C17B 118.9(4) . . ?
C17A C18A C19A 120.0(4) . . ?
C18B C17B C16B 120.8(4) . . ?
C14A C19A C18A 119.8(3) . . ?
C19B C18B C17B 120.7(4) . . ?
P1A C20A Br21 111.13(17) . . ?
P1A C20A Br22 110.25(18) . . ?
Br21 C20A Br22 108.71(16) . . ?
P1B C20B Br4C 110.56(18) . . ?
P1B C20B Br3C 108.57(18) . . ?
Br4C C20B Br3C 111.65(18) . . ?
C18B C19B C14B 120.0(4) . . ?
C2B P1B C8B 111.65(18) . . ?
C2B P1B C14B 111.76(18) . . ?
C8B P1B C14B 106.13(17) . . ?
C2B P1B C20B 109.73(18) . . ?
C8B P1B C20B 108.73(17) . . ?
C14B P1B C20B 108.72(17) . . ?

_refine_diff_density_max         0.688
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.100




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_nitromethane
_database_code_depnum_ccdc_archive 'CCDC 2095088'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT434_1_nitromethane      
;
PROBLEM: Short Inter HL..HL Contact Br21     ..Br23             3.19 Ang.  
RESPONSE: As a result of halogen-halogen bonding.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'dibromomethyl)triphenylphosphonium bromide nitromethane solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Br3 N O2 P'
_chemical_formula_weight         576.06

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   32.270(2)
_cell_length_b                   32.270(2)
_cell_length_c                   11.3230(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10211.4(15)
_cell_formula_units_Z            18
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4049
_cell_measurement_theta_min      4.213
_cell_measurement_theta_max      72.736

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_F_000             5076
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    7.381
_shelx_estimated_absorpt_T_min   0.352
_shelx_estimated_absorpt_T_max   0.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4432
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17041
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.213
_diffrn_reflns_theta_max         72.736
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4416
_reflns_number_gt                4049
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0116P)²+47.6886P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4416
_refine_ls_number_parameters     245
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0647
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.16139(2) 0.41614(2) 0.57990(5) 0.02260(13) Uani 1 1 d . . . . .
C2 C 0.20277(9) 0.47856(9) 0.5579(2) 0.0286(5) Uani 1 1 d . . . . .
C3 C 0.25170(10) 0.49476(11) 0.5490(3) 0.0399(7) Uani 1 1 d . . . . .
H3 H 0.263566 0.473418 0.560726 0.048 Uiso 1 1 calc R U . . .
C4 C 0.28265(13) 0.54253(14) 0.5227(3) 0.0577(9) Uani 1 1 d . . . . .
H4 H 0.316058 0.554129 0.517375 0.069 Uiso 1 1 calc R U . . .
C5 C 0.26538(15) 0.57315(13) 0.5042(4) 0.0623(10) Uani 1 1 d . . . . .
H5 H 0.286943 0.605675 0.485106 0.075 Uiso 1 1 calc R U . . .
C6 C 0.21735(15) 0.55738(12) 0.5131(3) 0.0551(9) Uani 1 1 d . . . . .
H6 H 0.205813 0.578952 0.500571 0.066 Uiso 1 1 calc R U . . .
C7 C 0.18576(11) 0.50995(10) 0.5403(3) 0.0390(6) Uani 1 1 d . . . . .
H7 H 0.152494 0.498937 0.546929 0.047 Uiso 1 1 calc R U . . .
C8 C 0.11110(9) 0.40936(9) 0.6638(2) 0.0253(5) Uani 1 1 d . . . . .
C9 C 0.12063(10) 0.43898(10) 0.7614(2) 0.0333(6) Uani 1 1 d . . . . .
H9 H 0.152364 0.463847 0.777090 0.040 Uiso 1 1 calc R U . . .
C10 C 0.08343(12) 0.43195(12) 0.8355(3) 0.0400(7) Uani 1 1 d . . . . .
H10 H 0.089725 0.451840 0.902782 0.048 Uiso 1 1 calc R U . . .
C11 C 0.03741(11) 0.39617(12) 0.8118(3) 0.0383(7) Uani 1 1 d . . . . .
H11 H 0.011993 0.391961 0.861997 0.046 Uiso 1 1 calc R U . . .
C12 C 0.02786(10) 0.36630(11) 0.7156(3) 0.0344(6) Uani 1 1 d . . . . .
H12 H -0.003978 0.341474 0.700741 0.041 Uiso 1 1 calc R U . . .
C13 C 0.06457(9) 0.37244(10) 0.6407(2) 0.0286(5) Uani 1 1 d . . . . .
H13 H 0.058167 0.351872 0.574820 0.034 Uiso 1 1 calc R U . . .
C14 C 0.18997(9) 0.38897(10) 0.6578(2) 0.0278(5) Uani 1 1 d . . . . .
C15 C 0.18386(10) 0.34475(11) 0.6233(3) 0.0357(6) Uani 1 1 d . . . . .
H15 H 0.165367 0.328932 0.555423 0.043 Uiso 1 1 calc R U . . .
C16 C 0.20512(12) 0.32410(13) 0.6893(3) 0.0465(8) Uani 1 1 d . . . . .
H16 H 0.201351 0.294105 0.666204 0.056 Uiso 1 1 calc R U . . .
C17 C 0.23152(11) 0.34687(14) 0.7876(3) 0.0493(9) Uani 1 1 d . . . . .
H17 H 0.246375 0.332742 0.831400 0.059 Uiso 1 1 calc R U . . .
C18 C 0.23675(10) 0.38996(14) 0.8236(3) 0.0477(8) Uani 1 1 d . . . . .
H18 H 0.254500 0.404992 0.892930 0.057 Uiso 1 1 calc R U . . .
C19 C 0.21611(10) 0.41154(12) 0.7586(3) 0.0383(6) Uani 1 1 d . . . . .
H19 H 0.219849 0.441404 0.782922 0.046 Uiso 1 1 calc R U . . .
C20 C 0.14225(9) 0.38734(9) 0.4373(2) 0.0252(5) Uani 1 1 d . . . . .
H20 H 0.120642 0.352178 0.449012 0.030 Uiso 1 1 calc R U . . .
Br21 Br 0.10837(2) 0.41296(2) 0.34922(2) 0.02783(8) Uani 1 1 d . . . . .
Br22 Br 0.19849(2) 0.39808(2) 0.34814(2) 0.02884(9) Uani 1 1 d . . . . .
Br23 Br 0.27837(2) 0.40252(2) 0.17609(3) 0.04270(10) Uani 1 1 d . . . . .
C1B C 0.3791(3) 0.5407(3) 0.1792(5) 0.126(3) Uani 1 1 d . U . . .
H00I H 0.411045 0.561226 0.145899 0.189 Uiso 1 1 calc R U . . .
H00P H 0.354963 0.540506 0.126377 0.189 Uiso 1 1 calc R U . . .
H00Q H 0.373433 0.508024 0.187713 0.189 Uiso 1 1 calc R U . . .
N2B N 0.37607(19) 0.55837(17) 0.2909(4) 0.0853(12) Uani 1 1 d . U . . .
O3B O 0.3638(2) 0.5900(2) 0.2908(5) 0.1445(19) Uani 1 1 d . U . . .
O4B O 0.38227(15) 0.54551(13) 0.3811(3) 0.0878(10) Uani 1 1 d . 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
P1 C14 1.791(2) . ?
P1 C2 1.792(3) . ?
P1 C8 1.797(3) . ?
P1 C20 1.811(3) . ?
C2 C7 1.387(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.391(4) . ?
C8 C13 1.398(4) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.389(4) . ?
C14 C15 1.396(4) . ?
C15 C16 1.389(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.371(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 Br21 1.944(2) . ?
C20 Br22 1.950(2) . ?
C20 H20 1.0000 . ?
C1B N2B 1.411(6) . ?
C1B H00I 0.9800 . ?
C1B H00P 0.9800 . ?
C1B H00Q 0.9800 . ?
N2B O4B 1.157(5) . ?
N2B O3B 1.265(6) . ?

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
C14 P1 C2 110.00(12) . . ?
C14 P1 C8 109.55(11) . . ?
C2 P1 C8 109.30(12) . . ?
C14 P1 C20 108.37(12) . . ?
C2 P1 C20 108.90(12) . . ?
C8 P1 C20 110.70(12) . . ?
C7 C2 C3 120.2(3) . . ?
C7 C2 P1 119.7(2) . . ?
C3 C2 P1 119.9(2) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
C9 C8 C13 120.6(2) . . ?
C9 C8 P1 117.4(2) . . ?
C13 C8 P1 121.7(2) . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 118.9(3) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C19 C14 C15 120.3(3) . . ?
C19 C14 P1 118.3(2) . . ?
C15 C14 P1 121.2(2) . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 119.3(3) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
P1 C20 Br21 111.05(13) . . ?
P1 C20 Br22 108.79(12) . . ?
Br21 C20 Br22 109.28(12) . . ?
P1 C20 H20 109.2 . . ?
Br21 C20 H20 109.2 . . ?
Br22 C20 H20 109.2 . . ?
N2B C1B H00I 109.5 . . ?
N2B C1B H00P 109.5 . . ?
H00I C1B H00P 109.5 . . ?
N2B C1B H00Q 109.5 . . ?
H00I C1B H00Q 109.5 . . ?
H00P C1B H00Q 109.5 . . ?
O4B N2B O3B 118.0(5) . . ?
O4B N2B C1B 125.9(5) . . ?
O3B N2B C1B 116.0(5) . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.073






####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_MeCN
_database_code_depnum_ccdc_archive 'CCDC 2095087'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'(dibromomethyl)(triphenyl)phosphanium bromide acetonitrile solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Br3 N P'
_chemical_formula_weight         556.07

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   33.1499(5)
_cell_length_b                   33.1499(5)
_cell_length_c                   11.1629(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10623.6(4)
_cell_formula_units_Z            18
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4193
_cell_measurement_theta_min      4.249
_cell_measurement_theta_max      72.360

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             4896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.582
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.128
_exptl_absorpt_coefficient_mu    7.007
_shelx_estimated_absorpt_T_min   0.106
_shelx_estimated_absorpt_T_max   0.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3226
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25997
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         4.249
_diffrn_reflns_theta_max         72.360
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4593
_reflns_number_gt                4193
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+25.4169P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4593
_refine_ls_number_parameters     230
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.39171(13) 0.19012(11) 0.3405(3) 0.0576(8) Uani 1 1 d . . . A 1
P1 P 0.41749(3) 0.16140(3) 0.41987(7) 0.04705(18) Uani 1 1 d . . . A 1
Br23 Br 0.39654(2) 0.27482(2) 0.82681(4) 0.07561(15) Uani 1 1 d . . . B 1
Br22 Br 0.41338(2) 0.10844(2) 0.65276(3) 0.05745(12) Uani 1 1 d . . . A 1
Br21 Br 0.39801(2) 0.19595(2) 0.65660(3) 0.06008(13) Uani 1 1 d . . . A 1
C20 C 0.38913(11) 0.14219(11) 0.5639(3) 0.0496(6) Uani 1 1 d . . . A 1
H20 H 0.355692 0.121468 0.550787 0.059 Uiso 1 1 calc R U . A 1
C19 C 0.50900(15) 0.18492(18) 0.4582(4) 0.0797(11) Uani 1 1 d . . . A 1
H19 H 0.498664 0.153275 0.450846 0.096 Uiso 1 1 calc R U . A 1
C18 C 0.5550(2) 0.2158(3) 0.4839(6) 0.116(2) Uani 1 1 d . . . A 1
H18 H 0.575607 0.204774 0.493946 0.139 Uiso 1 1 calc R U . A 1
C17 C 0.5706(2) 0.2615(3) 0.4948(7) 0.128(2) Uani 1 1 d . . . A 1
H17 H 0.601867 0.281834 0.511854 0.154 Uiso 1 1 calc R U . A 1
C16 C 0.5406(2) 0.2782(2) 0.4806(6) 0.115(2) Uani 1 1 d . . . A 1
H16 H 0.551646 0.309971 0.488786 0.138 Uiso 1 1 calc R U . A 1
C15 C 0.49408(17) 0.24871(15) 0.4545(4) 0.0833(12) Uani 1 1 d . . . A 1
H15 H 0.473935 0.260347 0.444542 0.100 Uiso 1 1 calc R U . A 1
C14 C 0.47806(12) 0.20147(12) 0.4433(3) 0.0588(7) Uani 1 1 d . . . A 1
C13 C 0.37480(13) 0.06780(12) 0.3552(3) 0.0587(8) Uani 1 1 d . . . A 1
H13 H 0.354995 0.061714 0.420191 0.070 Uiso 1 1 calc R U . A 1
C12 C 0.36854(16) 0.03192(14) 0.2787(4) 0.0725(10) Uani 1 1 d . . . A 1
H12 H 0.344421 0.001709 0.292394 0.087 Uiso 1 1 calc R U . A 1
C11 C 0.39775(19) 0.04103(18) 0.1834(4) 0.0808(12) Uani 1 1 d . . . A 1
H11 H 0.393699 0.016819 0.133450 0.097 Uiso 1 1 calc R U . A 1
C10 C 0.43283(19) 0.0853(2) 0.1608(4) 0.0878(13) Uani 1 1 d . . . A 1
H10 H 0.452104 0.091057 0.094866 0.105 Uiso 1 1 calc R U . A 1
C9 C 0.43999(16) 0.12170(16) 0.2352(4) 0.0735(10) Uani 1 1 d . . . A 1
H9 H 0.463946 0.151830 0.219628 0.088 Uiso 1 1 calc R U . A 1
C8 C 0.41082(11) 0.11261(11) 0.3336(3) 0.0514(7) Uani 1 1 d . . . A 1
C7 C 0.34921(16) 0.18481(15) 0.3748(4) 0.0740(10) Uani 1 1 d . U . A 1
H7 H 0.333504 0.166959 0.441296 0.089 Uiso 1 1 calc R U . A 1
C6 C 0.3306(2) 0.20684(19) 0.3072(6) 0.0995(17) Uani 1 1 d . U . A 1
H6 H 0.302133 0.203816 0.329361 0.119 Uiso 1 1 calc R U . A 1
C5 C 0.3530(2) 0.23255(17) 0.2098(5) 0.1001(16) Uani 1 1 d . U . A 1
H5 H 0.340303 0.247642 0.167249 0.120 Uiso 1 1 calc R U . A 1
C4 C 0.3938(2) 0.23655(15) 0.1736(5) 0.0988(16) Uani 1 1 d . U . A 1
H4 H 0.408318 0.253453 0.104882 0.119 Uiso 1 1 calc R U . A 1
C3 C 0.41432(18) 0.21548(14) 0.2387(4) 0.0795(11) Uani 1 1 d . U . A 1
H3 H 0.442495 0.218389 0.214479 0.095 Uiso 1 1 calc R U . A 1
N1B N 0.5499(7) 0.3817(6) 0.6310(15) 0.180(4) Uiso 0.629(11) 1 d D . P C 1
C3B C 0.5230(8) 0.3306(8) 0.8286(17) 0.251(11) Uiso 0.629(11) 1 d D . P C 1
H3B1 H 0.489618 0.313108 0.829615 0.377 Uiso 0.629(11) 1 calc R U P C 1
H3B2 H 0.534106 0.349484 0.899403 0.377 Uiso 0.629(11) 1 calc R U P C 1
H3B3 H 0.535018 0.309553 0.826379 0.377 Uiso 0.629(11) 1 calc R U P C 1
C2B C 0.5387(6) 0.3603(6) 0.7234(15) 0.179(5) Uiso 0.629(11) 1 d D . P C 1
N1C N 0.5571(10) 0.3736(9) 0.586(2) 0.180(4) Uiso 0.371(11) 1 d D . P C 2
C2C C 0.5459(10) 0.3866(10) 0.674(3) 0.179(5) Uiso 0.371(11) 1 d D . P C 2
C3C C 0.5266(10) 0.3972(10) 0.778(2) 0.179(5) Uiso 0.371(11) 1 d D . P C 2
H3C1 H 0.513880 0.416389 0.754627 0.269 Uiso 0.371(11) 1 calc R U P C 2
H3C2 H 0.550733 0.413406 0.836461 0.269 Uiso 0.371(11) 1 calc R U P C 2
H3C3 H 0.502452 0.368717 0.812361 0.269 Uiso 0.371(11) 1 calc R U P C 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
C2 C7 1.383(6) . ?
C2 C3 1.389(6) . ?
C2 P1 1.799(3) . ?
P1 C14 1.788(4) . ?
P1 C8 1.799(3) . ?
P1 C20 1.810(3) . ?
Br22 C20 1.945(3) . ?
Br21 C20 1.952(3) . ?
C20 H20 0.9800 . ?
C19 C18 1.377(8) . ?
C19 C14 1.394(6) . ?
C19 H19 0.9300 . ?
C18 C17 1.337(11) . ?
C18 H18 0.9300 . ?
C17 C16 1.371(11) . ?
C17 H17 0.9300 . ?
C16 C15 1.382(8) . ?
C16 H16 0.9300 . ?
C15 C14 1.385(6) . ?
C15 H15 0.9300 . ?
C13 C8 1.385(5) . ?
C13 C12 1.394(5) . ?
C13 H13 0.9300 . ?
C12 C11 1.367(7) . ?
C12 H12 0.9300 . ?
C11 C10 1.365(7) . ?
C11 H11 0.9300 . ?
C10 C9 1.384(6) . ?
C10 H10 0.9300 . ?
C9 C8 1.394(5) . ?
C9 H9 0.9300 . ?
C7 C6 1.392(6) . ?
C7 H7 0.9300 . ?
C6 C5 1.352(9) . ?
C6 H6 0.9300 . ?
C5 C4 1.352(9) . ?
C5 H5 0.9300 . ?
C4 C3 1.398(7) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
N1B C2B 1.2003(18) . ?
C3B C2B 1.4516(18) . ?
C3B H3B1 0.9600 . ?
C3B H3B2 0.9600 . ?
C3B H3B3 0.9600 . ?
N1C C2C 1.2017(19) . ?
C2C C3C 1.4517(19) . ?
C3C H3C1 0.9600 . ?
C3C H3C2 0.9600 . ?
C3C H3C3 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
C7 C2 C3 120.7(3) . . ?
C7 C2 P1 121.3(3) . . ?
C3 C2 P1 117.9(3) . . ?
C14 P1 C8 109.49(16) . . ?
C14 P1 C2 109.45(16) . . ?
C8 P1 C2 109.57(14) . . ?
C14 P1 C20 108.93(15) . . ?
C8 P1 C20 110.52(14) . . ?
C2 P1 C20 108.85(16) . . ?
P1 C20 Br22 111.36(15) . . ?
P1 C20 Br21 109.58(15) . . ?
Br22 C20 Br21 109.74(14) . . ?
P1 C20 H20 108.7 . . ?
Br22 C20 H20 108.7 . . ?
Br21 C20 H20 108.7 . . ?
C18 C19 C14 119.4(5) . . ?
C18 C19 H19 120.3 . . ?
C14 C19 H19 120.3 . . ?
C17 C18 C19 121.3(6) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C17 C16 119.9(6) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C16 C15 121.1(6) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C15 C14 118.7(5) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C14 C19 119.5(4) . . ?
C15 C14 P1 120.4(3) . . ?
C19 C14 P1 119.9(3) . . ?
C8 C13 C12 119.3(4) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C9 C8 119.1(4) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C13 C8 C9 120.2(3) . . ?
C13 C8 P1 121.6(2) . . ?
C9 C8 P1 117.9(3) . . ?
C2 C7 C6 118.3(5) . . ?
C2 C7 H7 120.8 . . ?
C6 C7 H7 120.8 . . ?
C5 C6 C7 121.2(6) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C4 C3 120.5(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C2 C3 C4 118.5(5) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C2B C3B H3B1 109.5 . . ?
C2B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C2B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
N1B C2B C3B 175(2) . . ?
N1C C2C C3C 173(2) . . ?
C2C C3C H3C1 109.5 . . ?
C2C C3C H3C2 109.5 . . ?
H3C1 C3C H3C2 109.5 . . ?
C2C C3C H3C3 109.5 . . ?
H3C1 C3C H3C3 109.5 . . ?
H3C2 C3C H3C3 109.5 . . ?

_refine_diff_density_max         0.693
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.065







####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_aceticacid
_database_code_depnum_ccdc_archive 'CCDC 2095091'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT434_1_aceticacid        
;
PROBLEM: Short Inter HL..HL Contact Br21     ..Br23             3.22 Ang.  
RESPONSE: This is a result of halogen...halogen interactions.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'(dibromomethyl)(triphenyl)phosphanium bromide acetic acid solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 Br3 O2 P'
_chemical_formula_weight         575.07

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   32.4936(8)
_cell_length_b                   32.4936(8)
_cell_length_c                   11.3322(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10361.9(9)
_cell_formula_units_Z            18
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4197
_cell_measurement_theta_min      5.445
_cell_measurement_theta_max      72.361

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_F_000             5076
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    7.259
_shelx_estimated_absorpt_T_min   0.307
_shelx_estimated_absorpt_T_max   0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3139
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26075
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.445
_diffrn_reflns_theta_max         72.361
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             4447
_reflns_number_gt                4196
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+51.6894P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4447
_refine_ls_number_parameters     275
_refine_ls_number_restraints     309
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.228
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.41214(2) 0.49607(2) 0.25311(6) 0.02621(15) Uani 1 1 d . . . . .
C2 C 0.39156(11) 0.53728(11) 0.2760(3) 0.0341(6) Uani 1 1 d . . . . .
C3 C 0.34350(13) 0.52061(13) 0.2928(3) 0.0449(7) Uani 1 1 d . . . . .
H3 H 0.321147 0.487668 0.285527 0.054 Uiso 1 1 calc R U . . .
C10 C 0.54641(15) 0.53807(16) 0.1411(5) 0.0733(13) Uani 1 1 d . U . . .
H10 H 0.572083 0.533553 0.163226 0.088 Uiso 1 1 calc R U . . .
C11 C 0.55061(17) 0.56472(15) 0.0461(5) 0.0776(13) Uani 1 1 d . U . . .
H11 H 0.579609 0.579410 0.003161 0.093 Uiso 1 1 calc R U . . .
C12 C 0.5141(2) 0.57109(14) 0.0100(4) 0.0754(13) Uani 1 1 d . U . . .
H12 H 0.517542 0.589205 -0.058826 0.091 Uiso 1 1 calc R U . . .
C13 C 0.47109(17) 0.55071(13) 0.0753(4) 0.0601(11) Uani 1 1 d . . . . .
H13 H 0.445505 0.555086 0.051506 0.072 Uiso 1 1 calc R U . . .
C14 C 0.36886(9) 0.44545(10) 0.1714(3) 0.0300(6) Uani 1 1 d . . . . .
C15 C 0.34755(14) 0.45333(15) 0.0739(3) 0.0485(8) Uani 1 1 d . . . . .
H15 H 0.353702 0.484445 0.055728 0.058 Uiso 1 1 calc R U . . .
C16 C 0.31717(15) 0.4150(2) 0.0037(4) 0.0640(11) Uani 1 1 d . . . . .
H16 H 0.302475 0.419969 -0.062919 0.077 Uiso 1 1 calc R U . . .
C17 C 0.30806(12) 0.36955(16) 0.0296(4) 0.0568(10) Uani 1 1 d . . . . .
H17 H 0.286778 0.343534 -0.018324 0.068 Uiso 1 1 calc R U . . .
C18 C 0.32978(12) 0.36212(12) 0.1244(3) 0.0464(8) Uani 1 1 d . . . . .
H18 H 0.324012 0.331018 0.141017 0.056 Uiso 1 1 calc R U . . .
C19 C 0.36013(10) 0.39981(11) 0.1961(3) 0.0348(6) Uani 1 1 d . . . . .
H19 H 0.374945 0.394472 0.261942 0.042 Uiso 1 1 calc R U . . .
C20 C 0.42220(9) 0.47704(9) 0.3955(3) 0.0288(5) Uani 1 1 d . . . . .
H20 H 0.435572 0.455552 0.382974 0.035 Uiso 1 1 calc R U . . .
C1A C 0.2063(5) 0.5243(6) 0.6801(8) 0.150(5) Uani 0.555(6) 1 d D U P A 1
H1A1 H 0.175809 0.520482 0.706013 0.226 Uiso 0.555(6) 1 calc R U P A 1
H1A2 H 0.230973 0.557773 0.685934 0.226 Uiso 0.555(6) 1 calc R U P A 1
H1A3 H 0.214751 0.505094 0.730538 0.226 Uiso 0.555(6) 1 calc R U P A 1
C2A C 0.2025(3) 0.5092(5) 0.5635(10) 0.112(2) Uani 0.555(6) 1 d D U P A 1
O3A O 0.2382(4) 0.5264(5) 0.4968(10) 0.138(3) Uani 0.555(6) 1 d D U P A 1
O4A O 0.1600(3) 0.4832(4) 0.5108(8) 0.134(3) Uani 0.555(6) 1 d D U P A 1
H4A H 0.133218 0.474831 0.551557 0.201 Uiso 0.555(6) 1 d R U P A 1
C1B C 0.2302(6) 0.4876(7) 0.5191(13) 0.112(2) Uani 0.445(6) 1 d D U P A 2
C2B C 0.2046(8) 0.4780(8) 0.6212(19) 0.137(5) Uani 0.445(6) 1 d . U P A 2
H2B1 H 0.181229 0.488455 0.613508 0.206 Uiso 0.445(6) 1 calc R U P A 2
H2B2 H 0.226112 0.494816 0.686957 0.206 Uiso 0.445(6) 1 calc R U P A 2
H2B3 H 0.188144 0.443684 0.636394 0.206 Uiso 0.445(6) 1 calc R U P A 2
O2 O 0.2199(3) 0.5026(3) 0.4334(10) 0.090(3) Uani 0.445(6) 1 d D U P A 2
O4B O 0.2526(6) 0.4651(5) 0.5017(11) 0.136(4) Uani 0.445(6) 1 d . U P A 2
H4B H 0.260087 0.447674 0.549321 0.205 Uiso 0.445(6) 1 d R U P A 2
Br21 Br 0.36362(2) 0.44334(2) 0.48491(3) 0.03386(10) Uani 1 1 d . . . . .
Br22 Br 0.46768(2) 0.53250(2) 0.48503(3) 0.03637(11) Uani 1 1 d . . . . .
Br23 Br 0.54435(2) 0.61258(2) 0.65654(3) 0.04614(12) Uani 1 1 d . . . . .
C8 C 0.46747(11) 0.52426(10) 0.1745(3) 0.0390(7) Uani 1 1 d . . . . .
C7 C 0.42438(14) 0.58565(12) 0.2875(3) 0.0466(8) Uani 1 1 d . . . . .
H7 H 0.457355 0.597156 0.276619 0.056 Uiso 1 1 calc R U . . .
C6 C 0.40811(19) 0.61668(15) 0.3150(4) 0.0646(11) Uani 1 1 d . . . . .
H6 H 0.430068 0.649718 0.322388 0.078 Uiso 1 1 calc R U . . .
C5 C 0.3607(2) 0.60002(18) 0.3314(4) 0.0710(12) Uani 1 1 d . . . . .
H5 H 0.350108 0.621620 0.350688 0.085 Uiso 1 1 calc R U . . .
C4 C 0.32838(17) 0.55270(18) 0.3204(4) 0.0655(11) Uani 1 1 d . . . . .
H4 H 0.295514 0.541693 0.331638 0.079 Uiso 1 1 calc R U . . .
C9 C 0.50460(12) 0.51699(13) 0.2076(4) 0.0508(9) Uani 1 1 d . U . . .
H9 H 0.501558 0.497994 0.274402 0.061 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
P1 C2 1.790(3) . ?
P1 C8 1.794(3) . ?
P1 C14 1.796(3) . ?
P1 C20 1.815(3) . ?
C2 C3 1.386(5) . ?
C2 C7 1.396(5) . ?
C3 C4 1.393(5) . ?
C3 H3 0.9500 . ?
C10 C11 1.346(9) . ?
C10 C9 1.397(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.364(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.420(6) . ?
C12 H12 0.9500 . ?
C13 C8 1.384(6) . ?
C13 H13 0.9500 . ?
C14 C19 1.392(4) . ?
C14 C15 1.394(4) . ?
C15 C16 1.390(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.372(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 Br21 1.940(3) . ?
C20 Br22 1.949(3) . ?
C20 H20 1.0000 . ?
C1A C2A 1.393(10) . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 0.9800 . ?
C2A O3A 1.2586(15) . ?
C2A O4A 1.347(5) . ?
O4A H4A 0.8978 . ?
C1B O2 1.206(5) . ?
C1B O4B 1.28(2) . ?
C1B C2B 1.37(2) . ?
C2B H2B1 0.9800 . ?
C2B H2B2 0.9800 . ?
C2B H2B3 0.9800 . ?
O4B H4B 0.8976 . ?
C8 C9 1.392(5) . ?
C7 C6 1.388(5) . ?
C7 H7 0.9500 . ?
C6 C5 1.365(7) . ?
C6 H6 0.9500 . ?
C5 C4 1.367(7) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C9 H9 0.9500 . ?

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 P1 C8 110.12(14) . . ?
C2 P1 C14 110.21(14) . . ?
C8 P1 C14 109.74(14) . . ?
C2 P1 C20 108.91(13) . . ?
C8 P1 C20 108.07(15) . . ?
C14 P1 C20 109.76(13) . . ?
C3 C2 C7 120.3(3) . . ?
C3 C2 P1 119.8(2) . . ?
C7 C2 P1 119.7(3) . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 121.4(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 118.1(5) . . ?
C8 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C19 C14 C15 120.0(3) . . ?
C19 C14 P1 121.4(2) . . ?
C15 C14 P1 118.3(3) . . ?
C16 C15 C14 118.9(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.3(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
P1 C20 Br21 111.32(14) . . ?
P1 C20 Br22 109.28(14) . . ?
Br21 C20 Br22 109.06(14) . . ?
P1 C20 H20 109.0 . . ?
Br21 C20 H20 109.0 . . ?
Br22 C20 H20 109.0 . . ?
C2A C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
C2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
O3A C2A C1A 120.9(8) . . ?
O3A C2A O4A 116.2(12) . . ?
C1A C2A O4A 121.6(7) . . ?
C2A O4A H4A 119.7 . . ?
O2 C1B O4B 117.3(17) . . ?
O2 C1B C2B 121.0(17) . . ?
O4B C1B C2B 117.0(14) . . ?
C1B C2B H2B1 109.5 . . ?
C1B C2B H2B2 109.5 . . ?
H2B1 C2B H2B2 109.5 . . ?
C1B C2B H2B3 109.5 . . ?
H2B1 C2B H2B3 109.5 . . ?
H2B2 C2B H2B3 109.5 . . ?
C1B O4B H4B 132.6 . . ?
C13 C8 C9 120.8(3) . . ?
C13 C8 P1 118.2(3) . . ?
C9 C8 P1 120.8(3) . . ?
C6 C7 C2 119.0(4) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C8 C9 C10 119.0(4) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?

_refine_diff_density_max         0.898
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.076






####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_2-butanone
_database_code_depnum_ccdc_archive 'CCDC 2095090'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'(dibromomethyl)triphenylphosphonium bromide 2-butanone solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H24 Br3 O P'
_chemical_formula_weight         587.12

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   33.4263(4)
_cell_length_b                   33.4263(4)
_cell_length_c                   11.2099(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10847.0(3)
_cell_formula_units_Z            18
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4287
_cell_measurement_theta_min      4.229
_cell_measurement_theta_max      72.176

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_F_000             5220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.047
_exptl_absorpt_coefficient_mu    6.914
_shelx_estimated_absorpt_T_min   0.379
_shelx_estimated_absorpt_T_max   0.737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4304
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20559
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.229
_diffrn_reflns_theta_max         72.176
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4617
_reflns_number_gt                4287
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)²+24.0948P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4617
_refine_ls_number_parameters     266
_refine_ls_number_restraints     222
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0723
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C11A C 0.36385(15) 0.23446(11) 0.1937(4) 0.0771(11) Uani 1 1 d . . . . .
HN H 0.352789 0.250008 0.147666 0.093 Uiso 1 1 calc R U . . .
C12A C 0.34091(13) 0.21210(12) 0.2950(4) 0.0728(10) Uani 1 1 d . . . . .
HO H 0.314379 0.212644 0.317212 0.087 Uiso 1 1 calc R U . . .
C13A C 0.35661(10) 0.18847(10) 0.3657(3) 0.0539(7) Uani 1 1 d . . . . .
HC H 0.340360 0.172440 0.433264 0.065 Uiso 1 1 calc R U . . .
C14A C 0.48058(9) 0.19848(9) 0.4409(2) 0.0398(5) Uani 1 1 d . . . . .
C15A C 0.51005(10) 0.18093(11) 0.4611(3) 0.0544(6) Uani 1 1 d . . . . .
HD H 0.498742 0.149260 0.457518 0.065 Uiso 1 1 calc R U . . .
C16A C 0.55580(12) 0.21052(15) 0.4861(3) 0.0728(9) Uani 1 1 d . . . . .
HK H 0.575513 0.198862 0.499345 0.087 Uiso 1 1 calc R U . . .
C17A C 0.57252(12) 0.25712(15) 0.4917(4) 0.0789(10) Uani 1 1 d . . . . .
HM H 0.603566 0.276949 0.508710 0.095 Uiso 1 1 calc R U . . .
C18A C 0.54398(13) 0.27478(12) 0.4725(4) 0.0732(9) Uani 1 1 d . . . . .
HL H 0.555731 0.306517 0.476250 0.088 Uiso 1 1 calc R U . . .
C19A C 0.49761(11) 0.24560(10) 0.4474(3) 0.0539(6) Uani 1 1 d . . . . .
HE H 0.478129 0.257586 0.435120 0.065 Uiso 1 1 calc R U . . .
C20A C 0.39052(9) 0.14033(8) 0.5575(2) 0.0374(5) Uani 1 1 d . . . . .
H H 0.357450 0.120117 0.542266 0.045 Uiso 1 1 calc R U . . .
Br23 Br 0.39447(2) 0.27030(2) 0.83005(3) 0.05603(10) Uani 1 1 d . . . . .
Br22 Br 0.41341(2) 0.10556(2) 0.64513(2) 0.04450(9) Uani 1 1 d . . . . .
Br21 Br 0.39894(2) 0.19298(2) 0.65132(2) 0.04479(9) Uani 1 1 d . . . . .
O1B O 0.63252(11) 0.18196(12) 0.6027(3) 0.0998(9) Uani 1 1 d . . . . .
C10A C 0.40261(14) 0.23419(11) 0.1595(3) 0.0703(9) Uani 1 1 d . . . . .
HJ H 0.417538 0.248840 0.089242 0.084 Uiso 1 1 calc R U . . .
C9A C 0.42013(11) 0.21204(10) 0.2293(2) 0.0533(7) Uani 1 1 d . . . . .
HB H 0.447078 0.212345 0.207021 0.064 Uiso 1 1 calc R U . . .
C8A C 0.39687(9) 0.18945(8) 0.3328(2) 0.0400(5) Uani 1 1 d . . . . .
C7A C 0.44388(12) 0.11829(11) 0.2385(2) 0.0549(7) Uani 1 1 d . . . . .
HF H 0.469696 0.147353 0.227656 0.066 Uiso 1 1 calc R U . . .
C6A C 0.43615(14) 0.08210(14) 0.1638(3) 0.0686(9) Uani 1 1 d . . . . .
HG H 0.456618 0.086871 0.101952 0.082 Uiso 1 1 calc R U . . .
C5A C 0.39815(14) 0.03909(13) 0.1812(3) 0.0662(8) Uani 1 1 d . . . . .
HH H 0.393275 0.014823 0.131326 0.079 Uiso 1 1 calc R U . . .
C5B C 0.6809(5) 0.2409(6) 0.8063(12) 0.154(4) Uani 0.538(9) 1 d . U P A 1
H5B1 H 0.706019 0.251353 0.750692 0.232 Uiso 0.538(9) 1 calc R U P A 1
H5B2 H 0.692603 0.254809 0.882746 0.232 Uiso 0.538(9) 1 calc R U P A 1
H5B3 H 0.659121 0.249462 0.778212 0.232 Uiso 0.538(9) 1 calc R U P A 1
C4B C 0.6564(5) 0.1870(5) 0.8182(11) 0.115(3) Uani 0.538(9) 1 d . U P A 1
H4B1 H 0.678573 0.177600 0.840637 0.138 Uiso 0.538(9) 1 calc R U P A 1
H4B2 H 0.632440 0.176089 0.878544 0.138 Uiso 0.538(9) 1 calc R U P A 1
C6B C 0.6842(5) 0.2072(5) 0.7542(11) 0.112(4) Uani 0.462(9) 1 d . U P A 2
H6B1 H 0.708604 0.200223 0.737663 0.134 Uiso 0.462(9) 1 calc R U P A 2
H6B2 H 0.692740 0.236931 0.719383 0.134 Uiso 0.462(9) 1 calc R U P A 2
C7B C 0.6778(7) 0.2081(6) 0.8799(14) 0.154(4) Uani 0.462(9) 1 d . U P A 2
H7B1 H 0.648588 0.205921 0.895300 0.232 Uiso 0.462(9) 1 calc R U P A 2
H7B2 H 0.702167 0.236414 0.912371 0.232 Uiso 0.462(9) 1 calc R U P A 2
H7B3 H 0.678484 0.182419 0.916542 0.232 Uiso 0.462(9) 1 calc R U P A 2
C4A C 0.36745(12) 0.03155(11) 0.2709(3) 0.0587(7) Uani 1 1 d . . . . .
HI H 0.341936 0.002264 0.281527 0.070 Uiso 1 1 calc R U . . .
C3B C 0.6092(2) 0.1185(2) 0.7281(5) 0.132(2) Uani 1 1 d . . . . .
H3B1 H 0.577215 0.109557 0.736252 0.197 Uiso 1 1 calc R U . . .
H3B2 H 0.620202 0.112843 0.801727 0.197 Uiso 1 1 calc R U . . .
H3B3 H 0.612581 0.100826 0.665451 0.197 Uiso 1 1 calc R U . . .
C3A C 0.37416(10) 0.06744(9) 0.3464(2) 0.0457(6) Uani 1 1 d . . . . .
HA H 0.353111 0.062419 0.406859 0.055 Uiso 1 1 calc R U . . .
C2B C 0.63606(18) 0.1677(2) 0.6989(4) 0.0956(13) Uani 1 1 d . . . . .
C2A C 0.41266(9) 0.11081(8) 0.3302(2) 0.0385(5) Uani 1 1 d . . . . .
P1A P 0.42030(2) 0.15974(2) 0.41525(5) 0.03340(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11A C10A 1.355(6) . ?
C11A C12A 1.365(6) . ?
C11A HN 0.9300 . ?
C12A C13A 1.393(4) . ?
C12A HO 0.9300 . ?
C13A C8A 1.380(4) . ?
C13A HC 0.9300 . ?
C14A C19A 1.383(4) . ?
C14A C15A 1.394(4) . ?
C14A P1A 1.792(3) . ?
C15A C16A 1.372(5) . ?
C15A HD 0.9300 . ?
C16A C17A 1.368(6) . ?
C16A HK 0.9300 . ?
C17A C18A 1.367(6) . ?
C17A HM 0.9300 . ?
C18A C19A 1.386(5) . ?
C18A HL 0.9300 . ?
C19A HE 0.9300 . ?
C20A P1A 1.819(2) . ?
C20A Br21 1.946(2) . ?
C20A Br22 1.947(2) . ?
C20A H 0.9800 . ?
O1B C2B 1.209(6) . ?
C10A C9A 1.392(4) . ?
C10A HJ 0.9300 . ?
C9A C8A 1.391(4) . ?
C9A HB 0.9300 . ?
C8A P1A 1.797(2) . ?
C7A C6A 1.385(4) . ?
C7A C2A 1.395(4) . ?
C7A HF 0.9300 . ?
C6A C5A 1.376(6) . ?
C6A HG 0.9300 . ?
C5A C4A 1.367(5) . ?
C5A HH 0.9300 . ?
C5B C4B 1.57(2) . ?
C5B H5B1 0.9600 . ?
C5B H5B2 0.9600 . ?
C5B H5B3 0.9600 . ?
C4B C2B 1.493(12) . ?
C4B H4B1 0.9700 . ?
C4B H4B2 0.9700 . ?
C6B C7B 1.43(2) . ?
C6B C2B 1.610(15) . ?
C6B H6B1 0.9700 . ?
C6B H6B2 0.9700 . ?
C7B H7B1 0.9600 . ?
C7B H7B2 0.9600 . ?
C7B H7B3 0.9600 . ?
C4A C3A 1.391(4) . ?
C4A HI 0.9300 . ?
C3B C2B 1.463(8) . ?
C3B H3B1 0.9600 . ?
C3B H3B2 0.9600 . ?
C3B H3B3 0.9600 . ?
C3A C2A 1.388(4) . ?
C3A HA 0.9300 . ?
C2A P1A 1.798(2) . ?

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
C10A C11A C12A 120.6(3) . . ?
C10A C11A HN 119.7 . . ?
C12A C11A HN 119.7 . . ?
C11A C12A C13A 121.1(4) . . ?
C11A C12A HO 119.5 . . ?
C13A C12A HO 119.5 . . ?
C8A C13A C12A 118.3(3) . . ?
C8A C13A HC 120.8 . . ?
C12A C13A HC 120.8 . . ?
C19A C14A C15A 119.7(3) . . ?
C19A C14A P1A 120.3(2) . . ?
C15A C14A P1A 119.9(2) . . ?
C16A C15A C14A 119.8(3) . . ?
C16A C15A HD 120.1 . . ?
C14A C15A HD 120.1 . . ?
C17A C16A C15A 120.2(3) . . ?
C17A C16A HK 119.9 . . ?
C15A C16A HK 119.9 . . ?
C18A C17A C16A 120.6(3) . . ?
C18A C17A HM 119.7 . . ?
C16A C17A HM 119.7 . . ?
C17A C18A C19A 120.3(3) . . ?
C17A C18A HL 119.9 . . ?
C19A C18A HL 119.9 . . ?
C14A C19A C18A 119.4(3) . . ?
C14A C19A HE 120.3 . . ?
C18A C19A HE 120.3 . . ?
P1A C20A Br21 110.20(12) . . ?
P1A C20A Br22 110.30(12) . . ?
Br21 C20A Br22 110.16(11) . . ?
P1A C20A H 108.7 . . ?
Br21 C20A H 108.7 . . ?
Br22 C20A H 108.7 . . ?
C11A C10A C9A 120.2(3) . . ?
C11A C10A HJ 119.9 . . ?
C9A C10A HJ 119.9 . . ?
C8A C9A C10A 119.2(3) . . ?
C8A C9A HB 120.4 . . ?
C10A C9A HB 120.4 . . ?
C13A C8A C9A 120.6(2) . . ?
C13A C8A P1A 122.6(2) . . ?
C9A C8A P1A 116.7(2) . . ?
C6A C7A C2A 119.5(3) . . ?
C6A C7A HF 120.2 . . ?
C2A C7A HF 120.2 . . ?
C5A C6A C7A 119.9(3) . . ?
C5A C6A HG 120.1 . . ?
C7A C6A HG 120.1 . . ?
C4A C5A C6A 120.9(3) . . ?
C4A C5A HH 119.6 . . ?
C6A C5A HH 119.6 . . ?
C4B C5B H5B1 109.5 . . ?
C4B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
C4B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
C2B C4B C5B 106.4(10) . . ?
C2B C4B H4B1 110.4 . . ?
C5B C4B H4B1 110.4 . . ?
C2B C4B H4B2 110.4 . . ?
C5B C4B H4B2 110.4 . . ?
H4B1 C4B H4B2 108.6 . . ?
C7B C6B C2B 107.4(12) . . ?
C7B C6B H6B1 110.2 . . ?
C2B C6B H6B1 110.2 . . ?
C7B C6B H6B2 110.2 . . ?
C2B C6B H6B2 110.2 . . ?
H6B1 C6B H6B2 108.5 . . ?
C6B C7B H7B1 109.5 . . ?
C6B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C6B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C5A C4A C3A 120.4(3) . . ?
C5A C4A HI 119.8 . . ?
C3A C4A HI 119.8 . . ?
C2B C3B H3B1 109.5 . . ?
C2B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C2B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
C2A C3A C4A 119.1(3) . . ?
C2A C3A HA 120.4 . . ?
C4A C3A HA 120.4 . . ?
O1B C2B C3B 121.1(5) . . ?
O1B C2B C4B 137.9(7) . . ?
C3B C2B C4B 100.2(7) . . ?
O1B C2B C6B 106.0(7) . . ?
C3B C2B C6B 129.4(6) . . ?
C3A C2A C7A 120.2(2) . . ?
C3A C2A P1A 121.11(19) . . ?
C7A C2A P1A 118.3(2) . . ?
C14A P1A C8A 109.06(12) . . ?
C14A P1A C2A 109.85(12) . . ?
C8A P1A C2A 109.10(11) . . ?
C14A P1A C20A 109.52(11) . . ?
C8A P1A C20A 109.61(12) . . ?
C2A P1A C20A 109.69(11) . . ?

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.057





####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_acrylicacid
_database_code_depnum_ccdc_archive 'CCDC 2095092'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT434_1_acrylicacid       
;
PROBLEM: Short Inter HL..HL Contact Br24     ..Br25             3.20 Ang.  
RESPONSE: This is a result of halogen...halogen interactions.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'(dibromomethyl)(triphenyl)phosphanium bromide prop-2-enoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 Br3 O2 P'
_chemical_formula_weight         587.08

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   32.283(2)
_cell_length_b                   32.283(2)
_cell_length_c                   11.5522(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10426.7(15)
_cell_formula_units_Z            18
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4137
_cell_measurement_theta_min      4.141
_cell_measurement_theta_max      72.613

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_F_000             5184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.053
_exptl_absorpt_coefficient_mu    7.230
_shelx_estimated_absorpt_T_min   0.504
_shelx_estimated_absorpt_T_max   0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4885
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20408
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.141
_diffrn_reflns_theta_max         72.613
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4593
_reflns_number_gt                4137
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0210P)²+140.2643P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4593
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.58513(3) 0.50476(3) 0.24678(8) 0.0187(2) Uani 1 1 d . . . A 1
C2 C 0.62901(13) 0.55474(14) 0.3292(3) 0.0215(8) Uani 1 1 d . . . A 1
C3 C 0.63871(14) 0.60108(15) 0.3077(3) 0.0249(8) Uani 1 1 d . . . A 1
H3 H 0.624270 0.607597 0.243971 0.030 Uiso 1 1 calc R U . A 1
C4 C 0.66995(15) 0.63801(16) 0.3810(4) 0.0304(9) Uani 1 1 d . . . A 1
H4 H 0.676801 0.669846 0.367402 0.037 Uiso 1 1 calc R U . A 1
C5 C 0.69084(15) 0.62816(18) 0.4733(4) 0.0349(10) Uani 1 1 d . . . A 1
H5 H 0.712782 0.653525 0.521466 0.042 Uiso 1 1 calc R U . A 1
C6 C 0.68019(17) 0.5817(2) 0.4965(4) 0.0367(11) Uani 1 1 d . . . A 1
H6 H 0.694132 0.575389 0.561647 0.044 Uiso 1 1 calc R U . A 1
C7 C 0.64930(16) 0.54434(17) 0.4250(3) 0.0292(9) Uani 1 1 d . . . A 1
H7 H 0.641997 0.512476 0.440391 0.035 Uiso 1 1 calc R U . A 1
C8 C 0.52794(14) 0.47837(14) 0.3168(3) 0.0233(8) Uani 1 1 d . . . A 1
C9 C 0.52040(16) 0.44984(16) 0.4145(4) 0.0302(9) Uani 1 1 d . . . A 1
H9 H 0.544735 0.443961 0.441872 0.036 Uiso 1 1 calc R U . A 1
C10 C 0.47603(18) 0.43009(16) 0.4711(4) 0.0366(11) Uani 1 1 d . . . A 1
H10 H 0.470270 0.410591 0.537478 0.044 Uiso 1 1 calc R U . A 1
C11 C 0.44095(17) 0.43860(16) 0.4317(4) 0.0356(10) Uani 1 1 d . . . A 1
H11 H 0.410858 0.424243 0.469810 0.043 Uiso 1 1 calc R U . A 1
C12 C 0.44877(17) 0.46767(17) 0.3376(4) 0.0342(10) Uani 1 1 d . . . A 1
H12 H 0.424520 0.474065 0.312269 0.041 Uiso 1 1 calc R U . A 1
C13 C 0.49231(15) 0.48769(15) 0.2796(4) 0.0281(9) Uani 1 1 d . . . A 1
H13 H 0.497800 0.507774 0.214534 0.034 Uiso 1 1 calc R U . A 1
C15 C 0.60378(15) 0.46146(15) 0.2278(3) 0.0243(8) Uani 1 1 d . . . A 1
C16 C 0.65254(16) 0.47704(17) 0.2121(4) 0.0301(9) Uani 1 1 d . . . A 1
H16 H 0.675769 0.510017 0.218317 0.036 Uiso 1 1 calc R U . A 1
C18 C 0.66635(19) 0.44356(19) 0.1872(4) 0.0396(11) Uani 1 1 d . . . A 1
H18 H 0.699286 0.453607 0.177760 0.048 Uiso 1 1 calc R U . A 1
C19 C 0.6326(2) 0.39592(19) 0.1762(5) 0.0460(12) Uani 1 1 d . . . A 1
H19 H 0.642302 0.373379 0.157924 0.055 Uiso 1 1 calc R U . A 1
C20 C 0.5844(2) 0.38053(18) 0.1916(5) 0.0430(12) Uani 1 1 d . . . A 1
H20 H 0.561447 0.347507 0.184644 0.052 Uiso 1 1 calc R U . A 1
O1A O 0.53470(15) 0.40747(17) 0.6539(3) 0.0572(10) Uani 1 1 d . . . B 1
H1A H 0.520281 0.401619 0.717573 0.086 Uiso 1 1 calc R U . B 1
C21 C 0.56975(17) 0.41296(16) 0.2168(4) 0.0316(9) Uani 1 1 d . . . A 1
H21 H 0.536727 0.402409 0.226701 0.038 Uiso 1 1 calc R U . A 1
C22 C 0.57749(13) 0.52439(14) 0.1053(3) 0.0213(7) Uani 1 1 d . . . A 1
H22 H 0.564258 0.546337 0.114974 0.026 Uiso 1 1 calc R U . A 1
Br23 Br 0.63701(2) 0.55723(2) 0.01943(3) 0.02418(12) Uani 1 1 d . . . A 1
Br24 Br 0.53171(2) 0.46787(2) 0.01845(3) 0.02451(12) Uani 1 1 d . . . A 1
Br25 Br 0.45653(2) 0.38502(2) -0.14797(4) 0.03091(13) Uani 1 1 d . . . C 1
C2A C 0.5816(2) 0.4318(2) 0.6722(5) 0.0471(13) Uani 1 1 d . . . B 1
O3A O 0.60868(15) 0.44414(15) 0.5891(4) 0.0559(10) Uani 1 1 d . . . B 1
C4A C 0.5978(2) 0.4410(3) 0.7935(6) 0.0628(17) Uani 1 1 d . . . B 1
H4A H 0.574809 0.430693 0.854044 0.075 Uiso 1 1 calc R U . B 1
C5A C 0.6416(3) 0.4625(4) 0.8177(9) 0.108(4) Uani 1 1 d . . . B 1
H5AA H 0.664724 0.472874 0.757421 0.129 Uiso 1 1 calc R U . B 1
H5AB H 0.651683 0.468268 0.896213 0.129 Uiso 1 1 calc R U . B 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C15 1.790(4) . ?
P1 C8 1.793(4) . ?
P1 C2 1.797(4) . ?
P1 C22 1.814(4) . ?
C2 C3 1.389(6) . ?
C2 C7 1.410(6) . ?
C3 C4 1.398(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(6) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.394(6) . ?
C8 C9 1.399(6) . ?
C9 C10 1.405(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.370(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 C21 1.398(6) . ?
C15 C16 1.405(6) . ?
C16 C18 1.390(7) . ?
C16 H16 0.9500 . ?
C18 C19 1.376(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(7) . ?
C20 H20 0.9500 . ?
O1A C2A 1.330(7) . ?
O1A H1A 0.8400 . ?
C21 H21 0.9500 . ?
C22 Br23 1.940(4) . ?
C22 Br24 1.955(4) . ?
C22 H22 1.0000 . ?
C2A O3A 1.222(7) . ?
C2A C4A 1.472(9) . ?
C4A C5A 1.258(11) . ?
C4A H4A 0.9500 . ?
C5A H5AA 0.9500 . ?
C5A H5AB 0.9500 . ?

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
C15 P1 C8 110.64(19) . . ?
C15 P1 C2 110.11(19) . . ?
C8 P1 C2 110.48(18) . . ?
C15 P1 C22 108.65(18) . . ?
C8 P1 C22 106.55(19) . . ?
C2 P1 C22 110.33(18) . . ?
C3 C2 C7 121.0(4) . . ?
C3 C2 P1 121.6(3) . . ?
C7 C2 P1 117.0(3) . . ?
C2 C3 C4 119.3(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.9(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 118.5(4) . . ?
C6 C7 H7 120.7 . . ?
C2 C7 H7 120.7 . . ?
C13 C8 C9 120.0(4) . . ?
C13 C8 P1 121.5(3) . . ?
C9 C8 P1 118.4(3) . . ?
C8 C9 C10 118.5(4) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 119.7(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.2(4) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C21 C15 C16 120.1(4) . . ?
C21 C15 P1 120.2(3) . . ?
C16 C15 P1 119.4(3) . . ?
C18 C16 C15 119.1(4) . . ?
C18 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C19 C18 C16 120.3(5) . . ?
C19 C18 H18 119.8 . . ?
C16 C18 H18 119.8 . . ?
C18 C19 C20 120.6(5) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C2A O1A H1A 109.5 . . ?
C20 C21 C15 119.6(4) . . ?
C20 C21 H21 120.2 . . ?
C15 C21 H21 120.2 . . ?
P1 C22 Br23 112.4(2) . . ?
P1 C22 Br24 107.92(19) . . ?
Br23 C22 Br24 109.14(18) . . ?
P1 C22 H22 109.1 . . ?
Br23 C22 H22 109.1 . . ?
Br24 C22 H22 109.1 . . ?
O3A C2A O1A 119.0(5) . . ?
O3A C2A C4A 124.0(6) . . ?
O1A C2A C4A 117.0(5) . . ?
C5A C4A C2A 120.6(7) . . ?
C5A C4A H4A 119.7 . . ?
C2A C4A H4A 119.7 . . ?
C4A C5A H5AA 120.0 . . ?
C4A C5A H5AB 120.0 . . ?
H5AA C5A H5AB 120.0 . . ?

_refine_diff_density_max         2.949
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.116






####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_NMP
_database_code_depnum_ccdc_archive 'CCDC 2095094'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'(dibromomethyl)triphenylphosphonium bromide N-Methylpyrrolidone solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 Br3 N O P'
_chemical_formula_weight         614.15

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   33.612(2)
_cell_length_b                   33.612(2)
_cell_length_c                   11.4292(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11182.4(17)
_cell_formula_units_Z            18
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3388
_cell_measurement_theta_min      2.629
_cell_measurement_theta_max      72.170

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             5472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    6.750
_shelx_estimated_absorpt_T_min   0.209
_shelx_estimated_absorpt_T_max   0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4904
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76439
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0943
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.629
_diffrn_reflns_theta_max         72.170
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4907
_reflns_number_gt                3388
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+70.9250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4907
_refine_ls_number_parameters     272
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.84218(5) 0.58184(5) 0.40760(10) 0.0534(3) Uani 1 1 d . . . . .
C2 C 0.89095(19) 0.58974(19) 0.3244(4) 0.0572(12) Uani 1 1 d . . . . .
C3 C 0.93424(19) 0.6274(2) 0.3406(5) 0.0634(13) Uani 1 1 d . . . . .
H3 H 0.939308 0.648258 0.400141 0.076 Uiso 1 1 calc R U . . .
C5 C 0.9623(3) 0.6037(3) 0.1793(6) 0.086(2) Uani 1 1 d . . . . .
H5 H 0.986429 0.608391 0.130516 0.103 Uiso 1 1 calc R U . . .
C4 C 0.9700(2) 0.6340(2) 0.2682(6) 0.0785(17) Uani 1 1 d . . . . .
H4 H 0.999288 0.658940 0.279977 0.094 Uiso 1 1 calc R U . . .
C8 C 0.80468(19) 0.52177(19) 0.4335(4) 0.0564(12) Uani 1 1 d . . . . .
C6 C 0.9196(3) 0.5666(3) 0.1612(5) 0.089(2) Uani 1 1 d . . . . .
H6 H 0.914885 0.546381 0.100116 0.107 Uiso 1 1 calc R U . . .
C7 C 0.8832(2) 0.5588(2) 0.2332(5) 0.0730(16) Uani 1 1 d . . . . .
H7 H 0.854137 0.533558 0.221223 0.088 Uiso 1 1 calc R U . . .
C9 C 0.7570(2) 0.5034(2) 0.4358(5) 0.0658(14) Uani 1 1 d . . . . .
H9 H 0.744306 0.522041 0.423591 0.079 Uiso 1 1 calc R U . . .
C10 C 0.7292(2) 0.4569(3) 0.4566(5) 0.0809(18) Uani 1 1 d . . . . .
H10 H 0.697439 0.443969 0.455111 0.097 Uiso 1 1 calc R U . . .
C11 C 0.7480(3) 0.4295(2) 0.4796(6) 0.0840(19) Uani 1 1 d . . . . .
H11 H 0.728863 0.398403 0.495272 0.101 Uiso 1 1 calc R U . . .
C12 C 0.7945(3) 0.4476(2) 0.4795(5) 0.0785(18) Uani 1 1 d . . . . .
H12 H 0.806763 0.428776 0.495953 0.094 Uiso 1 1 calc R U . . .
C13 C 0.8234(2) 0.4934(2) 0.4554(5) 0.0671(14) Uani 1 1 d . . . . .
H13 H 0.855058 0.505466 0.453631 0.080 Uiso 1 1 calc R U . . .
C14 C 0.81195(18) 0.60441(19) 0.3278(4) 0.0566(12) Uani 1 1 d . . . . .
C15 C 0.78951(19) 0.5809(2) 0.2250(5) 0.0653(14) Uani 1 1 d . . . . .
H15 H 0.789941 0.554443 0.203073 0.078 Uiso 1 1 calc R U . . .
C16 C 0.7668(2) 0.5972(3) 0.1565(6) 0.0788(18) Uani 1 1 d . . . . .
H16 H 0.752587 0.582371 0.087212 0.095 Uiso 1 1 calc R U . . .
C17 C 0.7654(2) 0.6356(3) 0.1920(6) 0.086(2) Uani 1 1 d . . . . .
H17 H 0.748841 0.645750 0.148186 0.103 Uiso 1 1 calc R U . . .
C18 C 0.7879(2) 0.6591(2) 0.2903(7) 0.0842(19) Uani 1 1 d . . . . .
H18 H 0.787416 0.685562 0.311337 0.101 Uiso 1 1 calc R U . . .
C19 C 0.8115(2) 0.6436(2) 0.3593(5) 0.0699(15) Uani 1 1 d . . . . .
H19 H 0.826802 0.659670 0.426285 0.084 Uiso 1 1 calc R U . . .
C20 C 0.86104(19) 0.61182(19) 0.5466(4) 0.0594(12) Uani 1 1 d . . . . .
H20 H 0.880195 0.644783 0.530969 0.071 Uiso 1 1 calc R U . . .
Br21 Br 0.80834(2) 0.60205(2) 0.63927(5) 0.06878(19) Uani 1 1 d . . . . .
Br22 Br 0.89746(2) 0.59138(2) 0.63274(5) 0.06827(19) Uani 1 1 d . . . . .
Br23 Br 0.72988(3) 0.60435(2) 0.83024(6) 0.0793(2) Uani 1 1 d . . . . .
N24 N 0.6333(2) 0.4736(2) 0.7596(5) 0.0839(15) Uani 1 1 d . . . . .
C25 C 0.6477(2) 0.4575(3) 0.6759(6) 0.0830(18) Uani 1 1 d . U . . .
C26 C 0.6817(3) 0.4462(4) 0.7292(7) 0.131(3) Uani 1 1 d . U . . .
H00X H 0.671997 0.414024 0.717584 0.157 Uiso 1 1 calc R U . . .
H00Y H 0.711788 0.464725 0.694100 0.157 Uiso 1 1 calc R U . . .
C27 C 0.6831(3) 0.4568(4) 0.8565(7) 0.125(3) Uani 1 1 d . U . . .
H00V H 0.714347 0.478285 0.880475 0.150 Uiso 1 1 calc R U . . .
H00W H 0.671995 0.428923 0.902387 0.150 Uiso 1 1 calc R U . . .
C28 C 0.6531(3) 0.4772(3) 0.8745(6) 0.091(2) Uani 1 1 d . U . . .
H00M H 0.629413 0.460055 0.932179 0.109 Uiso 1 1 calc R U . . .
H28 H 0.670851 0.509022 0.899296 0.109 Uiso 1 1 calc R U . . .
C29 C 0.6028(4) 0.4915(4) 0.7387(7) 0.127(3) Uani 1 1 d . . . . .
H29 H 0.597672 0.491692 0.656179 0.190 Uiso 1 1 calc R U . . .
H00T H 0.616417 0.522225 0.768704 0.190 Uiso 1 1 calc R U . . .
H00U H 0.574047 0.472404 0.777464 0.190 Uiso 1 1 calc R U . . .
O30 O 0.63552(17) 0.45163(19) 0.5727(4) 0.0917(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C8 1.791(6) . ?
P1 C14 1.792(5) . ?
P1 C2 1.796(5) . ?
P1 C20 1.817(5) . ?
C2 C3 1.383(8) . ?
C2 C7 1.401(8) . ?
C3 C4 1.383(8) . ?
C3 H3 0.9300 . ?
C5 C6 1.367(10) . ?
C5 C4 1.369(10) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C8 C9 1.400(8) . ?
C8 C13 1.402(8) . ?
C6 C7 1.387(9) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C10 1.382(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(9) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.373(8) . ?
C14 C15 1.407(8) . ?
C15 C16 1.385(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 Br22 1.944(6) . ?
C20 Br21 1.946(5) . ?
C20 H20 0.9800 . ?
N24 C25 1.307(8) . ?
N24 C29 1.442(10) . ?
N24 C28 1.449(8) . ?
C25 O30 1.231(8) . ?
C25 C26 1.503(11) . ?
C26 C27 1.493(11) . ?
C26 H00X 0.9700 . ?
C26 H00Y 0.9700 . ?
C27 C28 1.494(11) . ?
C27 H00V 0.9700 . ?
C27 H00W 0.9700 . ?
C28 H00M 0.9700 . ?
C28 H28 0.9700 . ?
C29 H29 0.9600 . ?
C29 H00T 0.9600 . ?
C29 H00U 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
C8 P1 C14 109.5(3) . . ?
C8 P1 C2 109.3(3) . . ?
C14 P1 C2 109.7(2) . . ?
C8 P1 C20 109.5(2) . . ?
C14 P1 C20 108.9(3) . . ?
C2 P1 C20 109.9(3) . . ?
C3 C2 C7 119.9(5) . . ?
C3 C2 P1 122.0(4) . . ?
C7 C2 P1 117.8(4) . . ?
C2 C3 C4 120.0(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C6 C5 C4 120.9(6) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C4 C3 119.9(7) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C9 C8 C13 120.0(5) . . ?
C9 C8 P1 120.4(4) . . ?
C13 C8 P1 119.6(4) . . ?
C5 C6 C7 120.4(7) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 118.9(6) . . ?
C6 C7 H7 120.5 . . ?
C2 C7 H7 120.5 . . ?
C10 C9 C8 118.7(6) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C10 C9 120.7(6) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.5(7) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.6(6) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 119.3(6) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
C19 C14 C15 119.9(5) . . ?
C19 C14 P1 123.6(4) . . ?
C15 C14 P1 116.4(4) . . ?
C16 C15 C14 119.8(6) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 119.3(6) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C16 121.1(6) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.4(7) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.5(6) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
P1 C20 Br22 110.7(3) . . ?
P1 C20 Br21 110.3(3) . . ?
Br22 C20 Br21 110.2(2) . . ?
P1 C20 H20 108.5 . . ?
Br22 C20 H20 108.5 . . ?
Br21 C20 H20 108.5 . . ?
C25 N24 C29 122.6(6) . . ?
C25 N24 C28 116.6(6) . . ?
C29 N24 C28 120.5(6) . . ?
O30 C25 N24 127.3(7) . . ?
O30 C25 C26 125.6(7) . . ?
N24 C25 C26 107.1(6) . . ?
C27 C26 C25 105.8(7) . . ?
C27 C26 H00X 110.6 . . ?
C25 C26 H00X 110.6 . . ?
C27 C26 H00Y 110.6 . . ?
C25 C26 H00Y 110.6 . . ?
H00X C26 H00Y 108.7 . . ?
C26 C27 C28 107.2(7) . . ?
C26 C27 H00V 110.3 . . ?
C28 C27 H00V 110.3 . . ?
C26 C27 H00W 110.3 . . ?
C28 C27 H00W 110.3 . . ?
H00V C27 H00W 108.5 . . ?
N24 C28 C27 103.0(6) . . ?
N24 C28 H00M 111.2 . . ?
C27 C28 H00M 111.2 . . ?
N24 C28 H28 111.2 . . ?
C27 C28 H28 111.2 . . ?
H00M C28 H28 109.1 . . ?
N24 C29 H29 109.5 . . ?
N24 C29 H00T 109.5 . . ?
H29 C29 H00T 109.5 . . ?
N24 C29 H00U 109.5 . . ?
H29 C29 H00U 109.5 . . ?
H00T C29 H00U 109.5 . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.081






####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_DMSO
_database_code_depnum_ccdc_archive 'CCDC 2095093'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'(dibromomethyl)triphenylphosphonium bromide dimethylsulfoxide solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 Br3 O P S'
_chemical_formula_weight         593.14

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   33.4643(5)
_cell_length_b                   33.4643(5)
_cell_length_c                   11.1613(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10824.5(4)
_cell_formula_units_Z            18
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4423
_cell_measurement_theta_min      5.659
_cell_measurement_theta_max      72.198

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             5256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    7.725
_shelx_estimated_absorpt_T_min   0.422
_shelx_estimated_absorpt_T_max   0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3229
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61014
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.659
_diffrn_reflns_theta_max         72.198
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4702
_reflns_number_gt                4423
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+46.1974P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4702
_refine_ls_number_parameters     263
_refine_ls_number_restraints     309
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1059
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.41974(3) 0.25946(3) 0.41676(7) 0.03831(18) Uani 1 1 d . . . . .
S1S S 0.50330(18) 0.31392(19) -0.0336(4) 0.1434(11) Uani 0.570(4) 1 d D U P A 1
C2 C 0.47990(12) 0.28046(12) 0.4430(3) 0.0465(7) Uani 1 1 d . . . . .
Br03 Br 0.39531(2) 0.12396(2) 0.82987(4) 0.06111(14) Uani 1 1 d . . . . .
C3 C 0.50972(15) 0.32725(14) 0.4624(4) 0.0637(10) Uani 1 1 d . . . . .
H3 H 0.498912 0.347970 0.457977 0.076 Uiso 1 1 calc R U . . .
C10 C 0.4018(2) 0.1667(2) 0.1622(5) 0.0861(15) Uani 1 1 d . . . . .
H10 H 0.416997 0.166478 0.092609 0.103 Uiso 1 1 calc R U . . .
C7 C 0.49616(15) 0.24979(16) 0.4512(4) 0.0630(10) Uani 1 1 d . . . . .
H7 H 0.476237 0.218352 0.440150 0.076 Uiso 1 1 calc R U . . .
C6 C 0.54243(18) 0.2664(2) 0.4759(5) 0.0861(14) Uani 1 1 d . . . . .
H6 H 0.553792 0.246102 0.479911 0.103 Uiso 1 1 calc R U . . .
C5 C 0.57134(17) 0.3125(2) 0.4945(6) 0.0934(16) Uani 1 1 d . . . . .
H5 H 0.602290 0.323341 0.511680 0.112 Uiso 1 1 calc R U . . .
C4 C 0.55528(17) 0.34264(19) 0.4881(5) 0.0875(15) Uani 1 1 d . . . . .
H4 H 0.575326 0.373916 0.501256 0.105 Uiso 1 1 calc R U . . .
C3S C 0.5217(5) 0.3253(8) -0.1817(17) 0.183(6) Uani 0.570(4) 1 d D U P A 1
H3SA H 0.507056 0.340024 -0.221310 0.274 Uiso 0.570(4) 1 calc R U P A 1
H3SB H 0.513710 0.296861 -0.221791 0.274 Uiso 0.570(4) 1 calc R U P A 1
H3SC H 0.554591 0.345248 -0.183856 0.274 Uiso 0.570(4) 1 calc R U P A 1
C8 C 0.39619(12) 0.20650(11) 0.3337(3) 0.0463(7) Uani 1 1 d . . . . .
C9 C 0.41966(16) 0.20651(16) 0.2314(4) 0.0630(10) Uani 1 1 d . . . . .
H9 H 0.446963 0.232775 0.209367 0.076 Uiso 1 1 calc R U . . .
C11 C 0.3621(2) 0.1280(2) 0.1959(5) 0.0933(17) Uani 1 1 d . U . . .
H11 H 0.350867 0.101215 0.150427 0.112 Uiso 1 1 calc R U . . .
C13 C 0.35496(15) 0.16768(13) 0.3669(4) 0.0628(10) Uani 1 1 d . U . . .
H13 H 0.338629 0.167885 0.434062 0.075 Uiso 1 1 calc R U . . .
C14 C 0.41248(12) 0.30109(11) 0.3320(3) 0.0438(7) Uani 1 1 d . U . . .
C15 C 0.44357(16) 0.32485(15) 0.2398(4) 0.0625(10) Uani 1 1 d . U . . .
H15 H 0.469039 0.321187 0.227432 0.075 Uiso 1 1 calc R U . . .
C16 C 0.4361(2) 0.35380(17) 0.1670(4) 0.0767(12) Uani 1 1 d . U . . .
H16 H 0.456964 0.370113 0.106227 0.092 Uiso 1 1 calc R U . . .
C17 C 0.39852(19) 0.35871(15) 0.1835(4) 0.0723(11) Uani 1 1 d . U . . .
H17 H 0.393649 0.377947 0.132907 0.087 Uiso 1 1 calc R U . . .
C18 C 0.36753(16) 0.33546(14) 0.2745(4) 0.0642(10) Uani 1 1 d . U . . .
H18 H 0.342150 0.339380 0.285427 0.077 Uiso 1 1 calc R U . . .
C19 C 0.37414(13) 0.30627(12) 0.3496(3) 0.0509(8) Uani 1 1 d . U . . .
H19 H 0.353281 0.290404 0.410787 0.061 Uiso 1 1 calc R U . . .
C20 C 0.38997(11) 0.24914(11) 0.5599(3) 0.0414(6) Uani 1 1 d . U . . .
H20 H 0.356966 0.236499 0.544664 0.050 Uiso 1 1 calc R U . . .
Br21 Br 0.39808(2) 0.20467(2) 0.65338(3) 0.05030(13) Uani 1 1 d . U . . .
Br22 Br 0.41322(2) 0.30672(2) 0.64800(3) 0.05077(13) Uani 1 1 d . U . . .
C4S C 0.4427(2) 0.2783(5) -0.0538(13) 0.145(4) Uani 0.570(4) 1 d D U P A 1
H4S1 H 0.436850 0.260288 -0.125347 0.218 Uiso 0.570(4) 1 calc R U P A 1
H4S2 H 0.428863 0.297340 -0.060907 0.218 Uiso 0.570(4) 1 calc R U P A 1
H4S3 H 0.429797 0.258155 0.013847 0.218 Uiso 0.570(4) 1 calc R U P A 1
C12 C 0.3390(2) 0.12826(16) 0.2950(6) 0.0880(15) Uani 1 1 d . U . . .
H12 H 0.311875 0.101624 0.315994 0.106 Uiso 1 1 calc R U . . .
O2 O 0.5167(9) 0.2905(8) 0.0620(11) 0.146(4) Uani 0.570(4) 1 d D U P A 1
O2B O 0.5082(12) 0.2958(12) 0.0982(17) 0.146(4) Uani 0.430(4) 1 d . U P A 2
S1B S 0.5182(2) 0.2933(2) -0.0319(5) 0.1434(11) Uani 0.430(4) 1 d D U P A 2
C4B C 0.5376(6) 0.3489(3) -0.0948(16) 0.143(5) Uani 0.430(4) 1 d D U P A 2
H4BA H 0.544586 0.348606 -0.178128 0.214 Uiso 0.430(4) 1 calc R U P A 2
H4BB H 0.564818 0.371333 -0.053475 0.214 Uiso 0.430(4) 1 calc R U P A 2
H4BC H 0.513844 0.356882 -0.086864 0.214 Uiso 0.430(4) 1 calc R U P A 2
C3B C 0.4592(3) 0.2661(6) -0.0751(19) 0.145(4) Uani 0.430(4) 1 d D U P A 2
H3BA H 0.456742 0.260410 -0.159867 0.218 Uiso 0.430(4) 1 calc R U P A 2
H3BB H 0.446970 0.285825 -0.055797 0.218 Uiso 0.430(4) 1 calc R U P A 2
H3BC H 0.442145 0.237370 -0.033124 0.218 Uiso 0.430(4) 1 calc R 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 C2 1.794(4) . ?
P1 C8 1.796(3) . ?
P1 C14 1.798(3) . ?
P1 C20 1.822(3) . ?
S1S O2 1.519(2) . ?
S1S C3S 1.739(16) . ?
S1S C4S 1.779(2) . ?
C2 C7 1.384(5) . ?
C2 C3 1.390(5) . ?
C3 C4 1.374(7) . ?
C3 H3 0.9300 . ?
C10 C11 1.366(9) . ?
C10 C9 1.389(6) . ?
C10 H10 0.9300 . ?
C7 C6 1.387(6) . ?
C7 H7 0.9300 . ?
C6 C5 1.365(8) . ?
C6 H6 0.9300 . ?
C5 C4 1.363(9) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C3S H3SA 0.9600 . ?
C3S H3SB 0.9600 . ?
C3S H3SC 0.9600 . ?
C8 C9 1.386(6) . ?
C8 C13 1.391(6) . ?
C9 H9 0.9300 . ?
C11 C12 1.351(9) . ?
C11 H11 0.9300 . ?
C13 C12 1.402(6) . ?
C13 H13 0.9300 . ?
C14 C19 1.392(5) . ?
C14 C15 1.396(5) . ?
C15 C16 1.379(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.360(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 Br21 1.944(3) . ?
C20 Br22 1.946(3) . ?
C20 H20 0.9800 . ?
C4S H4S1 0.9600 . ?
C4S H4S2 0.9600 . ?
C4S H4S3 0.9600 . ?
C12 H12 0.9300 . ?
O2B S1B 1.50(2) . ?
S1B C3B 1.778(2) . ?
S1B C4B 1.781(2) . ?
C4B H4BA 0.9600 . ?
C4B H4BB 0.9600 . ?
C4B H4BC 0.9600 . ?
C3B H3BA 0.9600 . ?
C3B H3BB 0.9600 . ?
C3B H3BC 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
C2 P1 C8 108.88(16) . . ?
C2 P1 C14 110.02(16) . . ?
C8 P1 C14 109.30(15) . . ?
C2 P1 C20 109.36(15) . . ?
C8 P1 C20 109.69(16) . . ?
C14 P1 C20 109.58(15) . . ?
O2 S1S C3S 128.1(10) . . ?
O2 S1S C4S 106.0(12) . . ?
C3S S1S C4S 100.8(6) . . ?
C7 C2 C3 119.9(4) . . ?
C7 C2 P1 120.0(3) . . ?
C3 C2 P1 120.0(3) . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C11 C10 C9 120.3(5) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C2 C7 C6 119.4(4) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C5 C6 C7 120.1(5) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C4 C3 120.5(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
S1S C3S H3SA 109.5 . . ?
S1S C3S H3SB 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
S1S C3S H3SC 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
C9 C8 C13 121.1(3) . . ?
C9 C8 P1 117.1(3) . . ?
C13 C8 P1 121.7(3) . . ?
C8 C9 C10 119.1(5) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C8 C13 C12 117.4(5) . . ?
C8 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
C19 C14 C15 120.3(3) . . ?
C19 C14 P1 120.8(3) . . ?
C15 C14 P1 118.6(3) . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.7(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 119.0(4) . . ?
C18 C19 H19 120.5 . . ?
C14 C19 H19 120.5 . . ?
P1 C20 Br21 110.08(16) . . ?
P1 C20 Br22 110.20(16) . . ?
Br21 C20 Br22 110.30(15) . . ?
P1 C20 H20 108.7 . . ?
Br21 C20 H20 108.7 . . ?
Br22 C20 H20 108.7 . . ?
S1S C4S H4S1 109.5 . . ?
S1S C4S H4S2 109.5 . . ?
H4S1 C4S H4S2 109.5 . . ?
S1S C4S H4S3 109.5 . . ?
H4S1 C4S H4S3 109.5 . . ?
H4S2 C4S H4S3 109.5 . . ?
C11 C12 C13 121.7(5) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
O2B S1B C3B 94.0(16) . . ?
O2B S1B C4B 107.3(13) . . ?
C3B S1B C4B 99.16(15) . . ?
S1B C4B H4BA 109.5 . . ?
S1B C4B H4BB 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
S1B C4B H4BC 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
S1B C3B H3BA 109.5 . . ?
S1B C3B H3BB 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
S1B C3B H3BC 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?

_refine_diff_density_max         1.201
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.082






####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-DMF
_database_code_depnum_ccdc_archive 'CCDC 2095095'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'(dibromomethyl)triphenylphosphonium bromide dimethylformamide solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Br3 N O P'
_chemical_formula_weight         588.11

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   33.1823(9)
_cell_length_b                   33.1823(9)
_cell_length_c                   11.4506(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10918.7(7)
_cell_formula_units_Z            18
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3984
_cell_measurement_theta_min      2.663
_cell_measurement_theta_max      72.609

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             5220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    6.883
_shelx_estimated_absorpt_T_min   0.182
_shelx_estimated_absorpt_T_max   0.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4217
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            74379
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         72.609
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4798
_reflns_number_gt                3981
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²+56.2572P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4798
_refine_ls_number_parameters     255
_refine_ls_number_restraints     335
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.15888(4) 0.41528(4) 0.58494(8) 0.0510(2) Uani 1 1 d . . . . .
C2 C 0.18809(15) 0.39026(18) 0.6625(4) 0.0619(11) Uani 1 1 d . . . . .
C3 C 0.18511(19) 0.3493(2) 0.6297(5) 0.0774(14) Uani 1 1 d . . . . .
H3 H 0.167882 0.333117 0.564503 0.093 Uiso 1 1 calc R U . . .
C4 C 0.2088(2) 0.3321(3) 0.6972(7) 0.0999(19) Uani 1 1 d . U . . .
H4 H 0.207496 0.304464 0.675740 0.120 Uiso 1 1 calc R U . . .
C5 C 0.2335(2) 0.3555(3) 0.7930(6) 0.103(2) Uani 1 1 d . U . . .
H5 H 0.249462 0.343908 0.835155 0.123 Uiso 1 1 calc R U . . .
C9 C 0.06478(16) 0.37073(18) 0.6458(4) 0.0619(10) Uani 1 1 d . U . . .
H9 H 0.059457 0.350708 0.583444 0.074 Uiso 1 1 calc R U . . .
C10 C 0.02820(18) 0.3641(2) 0.7179(5) 0.0720(12) Uani 1 1 d . U . . .
H10 H -0.001817 0.339863 0.703583 0.086 Uiso 1 1 calc R U . . .
C11 C 0.0368(2) 0.3937(2) 0.8105(5) 0.0818(14) Uani 1 1 d . U . . .
H11 H 0.012304 0.389419 0.858410 0.098 Uiso 1 1 calc R U . . .
C12 C 0.0807(2) 0.4294(2) 0.8333(4) 0.0819(14) Uani 1 1 d . U . . .
H12 H 0.085911 0.448665 0.897219 0.098 Uiso 1 1 calc R U . . .
C13 C 0.11742(19) 0.4370(2) 0.7623(4) 0.0702(12) Uani 1 1 d . U . . .
H13 H 0.147226 0.461475 0.777360 0.084 Uiso 1 1 calc R U . . .
C14 C 0.19808(16) 0.47626(16) 0.5635(3) 0.0585(10) Uani 1 1 d . U . . .
C15 C 0.24584(18) 0.4936(2) 0.5551(4) 0.0744(13) Uani 1 1 d . U . . .
H15 H 0.258071 0.473946 0.563562 0.089 Uiso 1 1 calc R U . . .
C16 C 0.2749(2) 0.5408(3) 0.5339(5) 0.0986(18) Uani 1 1 d . U . . .
H16 H 0.306907 0.552952 0.528722 0.118 Uiso 1 1 calc R U . . .
C17 C 0.2568(3) 0.5696(2) 0.5206(6) 0.106(2) Uani 1 1 d . U . . .
H17 H 0.276698 0.601076 0.506490 0.127 Uiso 1 1 calc R U . . .
C18 C 0.2105(3) 0.5530(2) 0.5276(5) 0.0959(17) Uani 1 1 d . U . . .
H18 H 0.198814 0.573108 0.518420 0.115 Uiso 1 1 calc R U . . .
C19 C 0.1804(2) 0.50614(19) 0.5485(4) 0.0736(12) Uani 1 1 d . U . . .
H19 H 0.148470 0.494678 0.552493 0.088 Uiso 1 1 calc R U . . .
C20 C 0.14038(15) 0.38679(16) 0.4445(3) 0.0557(9) Uani 1 1 d . U . . .
H20 H 0.119881 0.353319 0.456751 0.067 Uiso 1 1 calc R U . . .
Br21 Br 0.19491(2) 0.39680(2) 0.35500(4) 0.06611(17) Uani 1 1 d . U . . .
Br22 Br 0.10679(2) 0.41110(2) 0.35673(4) 0.06221(16) Uani 1 1 d . U . . .
Br23 Br 0.27529(2) 0.39961(2) 0.17548(5) 0.0813(2) Uani 1 1 d . . . . .
O1A O 0.1786(3) 0.6279(3) 0.4350(6) 0.156(2) Uani 1 1 d . U . . .
C2A C 0.1883(6) 0.6359(4) 0.3316(11) 0.218(6) Uani 1 1 d . U . . .
H2A H 0.220124 0.655956 0.322942 0.262 Uiso 1 1 calc R U . . .
N3A N 0.1707(3) 0.6266(3) 0.2418(7) 0.159(3) Uani 1 1 d . U . . .
C4A C 0.1228(6) 0.5987(6) 0.2560(13) 0.261(8) Uani 1 1 d . U . . .
H4AA H 0.112231 0.569723 0.215793 0.392 Uiso 1 1 calc R U . . .
H4AB H 0.107427 0.614288 0.224395 0.392 Uiso 1 1 calc R U . . .
H4AC H 0.115601 0.592772 0.337611 0.392 Uiso 1 1 calc R U . . .
C5A C 0.1840(5) 0.6405(5) 0.1252(12) 0.202(5) Uani 1 1 d . U . . .
H5AA H 0.215309 0.666296 0.123408 0.302 Uiso 1 1 calc R U . . .
H5AB H 0.163424 0.649749 0.091043 0.302 Uiso 1 1 calc R U . . .
H5AC H 0.182370 0.615038 0.081606 0.302 Uiso 1 1 calc R U . . .
C7 C 0.21310(19) 0.4139(2) 0.7631(4) 0.0809(15) Uani 1 1 d . U . . .
H7 H 0.214832 0.441615 0.786043 0.097 Uiso 1 1 calc R U . . .
C8 C 0.10922(15) 0.40739(16) 0.6676(3) 0.0552(9) Uani 1 1 d . U . . .
C6 C 0.2354(2) 0.3948(3) 0.8279(6) 0.0999(19) Uani 1 1 d . U . . .
H6 H 0.251479 0.409565 0.895579 0.120 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
P1 C14 1.793(5) . ?
P1 C2 1.795(4) . ?
P1 C8 1.802(4) . ?
P1 C20 1.810(4) . ?
C2 C3 1.365(8) . ?
C2 C7 1.407(8) . ?
C3 C4 1.410(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.336(11) . ?
C5 H5 0.9300 . ?
C9 C8 1.387(7) . ?
C9 C10 1.392(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(7) . ?
C12 H12 0.9300 . ?
C13 C8 1.395(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.392(7) . ?
C14 C19 1.393(7) . ?
C15 C16 1.391(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.351(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 Br22 1.950(4) . ?
C20 Br21 1.958(4) . ?
C20 H20 0.9800 . ?
O1A C2A 1.222(13) . ?
C2A N3A 1.146(13) . ?
C2A H2A 0.9300 . ?
N3A C4A 1.394(17) . ?
N3A C5A 1.409(14) . ?
C4A H4AA 0.9600 . ?
C4A H4AB 0.9600 . ?
C4A H4AC 0.9600 . ?
C5A H5AA 0.9600 . ?
C5A H5AB 0.9600 . ?
C5A H5AC 0.9600 . ?
C7 C6 1.402(8) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 P1 C2 109.6(2) . . ?
C14 P1 C8 109.3(2) . . ?
C2 P1 C8 109.82(19) . . ?
C14 P1 C20 109.4(2) . . ?
C2 P1 C20 108.6(2) . . ?
C8 P1 C20 110.1(2) . . ?
C3 C2 C7 120.6(5) . . ?
C3 C2 P1 122.5(4) . . ?
C7 C2 P1 116.8(4) . . ?
C2 C3 C4 118.3(6) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 120.8(7) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 121.3(6) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C8 C9 C10 119.5(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 119.5(5) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 121.0(5) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.5(5) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 119.1(5) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C15 C14 C19 119.7(5) . . ?
C15 C14 P1 120.6(4) . . ?
C19 C14 P1 119.6(4) . . ?
C16 C15 C14 118.9(6) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C17 C16 C15 120.4(7) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 121.2(6) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.1(7) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 119.7(6) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
P1 C20 Br22 110.9(2) . . ?
P1 C20 Br21 109.5(2) . . ?
Br22 C20 Br21 109.3(2) . . ?
P1 C20 H20 109.0 . . ?
Br22 C20 H20 109.0 . . ?
Br21 C20 H20 109.0 . . ?
N3A C2A O1A 140.2(17) . . ?
N3A C2A H2A 109.9 . . ?
O1A C2A H2A 109.9 . . ?
C2A N3A C4A 109.4(13) . . ?
C2A N3A C5A 136.7(14) . . ?
C4A N3A C5A 113.3(10) . . ?
N3A C4A H4AA 109.5 . . ?
N3A C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
N3A C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
N3A C5A H5AA 109.5 . . ?
N3A C5A H5AB 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
N3A C5A H5AC 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C6 C7 C2 118.6(7) . . ?
C6 C7 H7 120.7 . . ?
C2 C7 H7 120.7 . . ?
C9 C8 C13 120.3(4) . . ?
C9 C8 P1 121.8(3) . . ?
C13 C8 P1 117.6(4) . . ?
C5 C6 C7 120.4(7) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?

_refine_diff_density_max         0.646
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.083





####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_DMA
_database_code_depnum_ccdc_archive 'CCDC 2095096'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'(dibromomethyl)triphenylphosphonium bromide dimethylacetamide solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 Br3 N O P'
_chemical_formula_weight         602.14

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   33.0726(18)
_cell_length_b                   33.0726(18)
_cell_length_c                   11.3690(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10769.3(13)
_cell_formula_units_Z            18
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4530
_cell_measurement_theta_min      4.184
_cell_measurement_theta_max      72.463

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_F_000             5364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    6.993
_shelx_estimated_absorpt_T_min   0.317
_shelx_estimated_absorpt_T_max   0.578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3589
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70134
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.184
_diffrn_reflns_theta_max         72.463
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4728
_reflns_number_gt                4530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+62.0066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4728
_refine_ls_number_parameters     265
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.50782(2) 0.59254(2) 0.24551(6) 0.02899(15) Uani 1 1 d . . . A 1
C2 C 0.47770(10) 0.53874(10) 0.1649(2) 0.0340(6) Uani 1 1 d . . . A 1
C3 C 0.47780(11) 0.49853(11) 0.1992(3) 0.0427(7) Uani 1 1 d . . . A 1
H3 H 0.493926 0.498310 0.268181 0.051 Uiso 1 1 calc R U . A 1
C4 C 0.45385(13) 0.45860(12) 0.1309(4) 0.0550(9) Uani 1 1 d . . . A 1
H4 H 0.452912 0.430577 0.154352 0.066 Uiso 1 1 calc R U . A 1
C5 C 0.43144(12) 0.45925(13) 0.0293(3) 0.0574(11) Uani 1 1 d . . . A 1
H5 H 0.415142 0.431618 -0.016316 0.069 Uiso 1 1 calc R U . A 1
C6 C 0.43239(11) 0.49922(13) -0.0066(3) 0.0512(9) Uani 1 1 d . . . A 1
H6 H 0.417500 0.499478 -0.077803 0.061 Uiso 1 1 calc R U . A 1
C7 C 0.45517(10) 0.53941(12) 0.0614(3) 0.0403(7) Uani 1 1 d . . . A 1
H7 H 0.455432 0.567102 0.037851 0.048 Uiso 1 1 calc R U . A 1
C8 C 0.55751(10) 0.63420(9) 0.1621(2) 0.0300(6) Uani 1 1 d . . . A 1
C9 C 0.54933(11) 0.65625(11) 0.0678(2) 0.0390(7) Uani 1 1 d . . . A 1
H9 H 0.518875 0.651335 0.053899 0.047 Uiso 1 1 calc R U . A 1
C10 C 0.58612(13) 0.68541(12) -0.0053(3) 0.0463(8) Uani 1 1 d . . . A 1
H10 H 0.580884 0.700462 -0.069895 0.056 Uiso 1 1 calc R U . A 1
C11 C 0.63015(12) 0.69247(11) 0.0158(3) 0.0454(8) Uani 1 1 d . . . A 1
H11 H 0.655252 0.712671 -0.034093 0.054 Uiso 1 1 calc R U . A 1
C12 C 0.63828(11) 0.67059(11) 0.1085(3) 0.0405(7) Uani 1 1 d . . . A 1
H12 H 0.668848 0.675708 0.121925 0.049 Uiso 1 1 calc R U . A 1
C13 C 0.60187(10) 0.64104(10) 0.1824(2) 0.0342(6) Uani 1 1 d . . . A 1
H13 H 0.607306 0.625720 0.245975 0.041 Uiso 1 1 calc R U . A 1
C14 C 0.46884(10) 0.61449(10) 0.2680(2) 0.0335(6) Uani 1 1 d . . . A 1
C15 C 0.42024(11) 0.58375(12) 0.2730(3) 0.0424(7) Uani 1 1 d . . . A 1
H15 H 0.407783 0.551134 0.262876 0.051 Uiso 1 1 calc R U . A 1
C16 C 0.39116(13) 0.60135(15) 0.2926(3) 0.0540(9) Uani 1 1 d . . . A 1
H16 H 0.358355 0.580773 0.295068 0.065 Uiso 1 1 calc R U . A 1
C17 C 0.40889(14) 0.64859(15) 0.3088(3) 0.0531(9) Uani 1 1 d . . . A 1
H17 H 0.388239 0.660287 0.321823 0.064 Uiso 1 1 calc R U . A 1
C18 C 0.45686(13) 0.67922(13) 0.3061(3) 0.0475(8) Uani 1 1 d . . . A 1
H18 H 0.468899 0.711674 0.318405 0.057 Uiso 1 1 calc R U . A 1
C19 C 0.48662(11) 0.66258(11) 0.2859(2) 0.0382(6) Uani 1 1 d . . . A 1
H19 H 0.519363 0.683488 0.283847 0.046 Uiso 1 1 calc R U . A 1
C20 C 0.52663(10) 0.58201(10) 0.3872(2) 0.0321(6) Uani 1 1 d . . . A 1
H20 H 0.547268 0.568395 0.373590 0.039 Uiso 1 1 calc R U . A 1
O1A O 0.48671(10) 0.78150(11) 0.4193(2) 0.0624(7) Uani 1 1 d . . . B 1
Br21 Br 0.47254(2) 0.53802(2) 0.47922(3) 0.04001(9) Uani 1 1 d . . . A 1
Br22 Br 0.56146(2) 0.64027(2) 0.47411(2) 0.03560(9) Uani 1 1 d . . . A 1
Br23 Br 0.39454(2) 0.45821(2) 0.66175(3) 0.04368(10) Uani 1 1 d . . . C 1
C2A C 0.49657(16) 0.79424(13) 0.5225(3) 0.0553(9) Uani 1 1 d . . . B 1
C3A C 0.54553(19) 0.82062(19) 0.5619(4) 0.0894(17) Uani 1 1 d . . . B 1
H3A H 0.551178 0.802264 0.620498 0.134 Uiso 1 1 calc R U . B 1
H00T H 0.551674 0.850224 0.597079 0.134 Uiso 1 1 calc R U . B 1
H00U H 0.566292 0.826930 0.494453 0.134 Uiso 1 1 calc R U . B 1
N4A N 0.46424(15) 0.78603(14) 0.6030(3) 0.0698(10) Uani 1 1 d . U . B 1
C5A C 0.4739(2) 0.80439(17) 0.7225(4) 0.0932(19) Uani 1 1 d . . . B 1
H00N H 0.494086 0.794804 0.761834 0.140 Uiso 1 1 calc R U . B 1
H00O H 0.444458 0.792178 0.765929 0.140 Uiso 1 1 calc R U . B 1
H5A H 0.489527 0.838555 0.719975 0.140 Uiso 1 1 calc R U . B 1
C6A C 0.4144(2) 0.7587(3) 0.5677(5) 0.116(2) Uani 1 1 d . U . B 1
H00V H 0.404404 0.779790 0.535909 0.174 Uiso 1 1 calc R U . B 1
H00W H 0.395337 0.742286 0.636374 0.174 Uiso 1 1 calc R U . B 1
H00X H 0.410699 0.735867 0.507402 0.174 Uiso 1 1 calc R U . B 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C14 1.786(3) . ?
P1 C2 1.796(3) . ?
P1 C8 1.798(3) . ?
P1 C20 1.822(3) . ?
C2 C3 1.388(5) . ?
C2 C7 1.398(4) . ?
C3 C4 1.389(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.390(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.387(4) . ?
C8 C9 1.397(4) . ?
C9 C10 1.389(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.407(4) . ?
C14 C15 1.409(4) . ?
C15 C16 1.368(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.366(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 Br22 1.948(3) . ?
C20 Br21 1.952(3) . ?
C20 H20 1.0000 . ?
O1A C2A 1.234(4) . ?
C2A N4A 1.329(5) . ?
C2A C3A 1.474(7) . ?
C3A H3A 0.9800 . ?
C3A H00T 0.9800 . ?
C3A H00U 0.9800 . ?
N4A C5A 1.456(5) . ?
N4A C6A 1.484(7) . ?
C5A H00N 0.9800 . ?
C5A H00O 0.9800 . ?
C5A H5A 0.9800 . ?
C6A H00V 0.9800 . ?
C6A H00W 0.9800 . ?
C6A H00X 0.9800 . ?

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
C14 P1 C2 108.67(14) . . ?
C14 P1 C8 109.46(13) . . ?
C2 P1 C8 109.37(12) . . ?
C14 P1 C20 109.63(13) . . ?
C2 P1 C20 109.58(14) . . ?
C8 P1 C20 110.11(13) . . ?
C3 C2 C7 120.6(3) . . ?
C3 C2 P1 122.7(2) . . ?
C7 C2 P1 116.7(2) . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 119.4(3) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C13 C8 C9 120.5(3) . . ?
C13 C8 P1 121.6(2) . . ?
C9 C8 P1 117.6(2) . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 119.2(3) . . ?
C8 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C19 C14 C15 119.4(3) . . ?
C19 C14 P1 120.1(2) . . ?
C15 C14 P1 120.5(2) . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
P1 C20 Br22 110.42(14) . . ?
P1 C20 Br21 110.07(14) . . ?
Br22 C20 Br21 109.48(13) . . ?
P1 C20 H20 108.9 . . ?
Br22 C20 H20 108.9 . . ?
Br21 C20 H20 108.9 . . ?
O1A C2A N4A 122.5(4) . . ?
O1A C2A C3A 121.1(4) . . ?
N4A C2A C3A 116.4(4) . . ?
C2A C3A H3A 109.5 . . ?
C2A C3A H00T 109.5 . . ?
H3A C3A H00T 109.5 . . ?
C2A C3A H00U 109.5 . . ?
H3A C3A H00U 109.5 . . ?
H00T C3A H00U 109.5 . . ?
C2A N4A C5A 124.9(4) . . ?
C2A N4A C6A 118.2(4) . . ?
C5A N4A C6A 116.8(4) . . ?
N4A C5A H00N 109.5 . . ?
N4A C5A H00O 109.5 . . ?
H00N C5A H00O 109.5 . . ?
N4A C5A H5A 109.5 . . ?
H00N C5A H5A 109.5 . . ?
H00O C5A H5A 109.5 . . ?
N4A C6A H00V 109.5 . . ?
N4A C6A H00W 109.5 . . ?
H00V C6A H00W 109.5 . . ?
N4A C6A H00X 109.5 . . ?
H00V C6A H00X 109.5 . . ?
H00W C6A H00X 109.5 . . ?

_refine_diff_density_max         0.696
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.065




####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_1_isobutyraldehyde
_database_code_depnum_ccdc_archive 'CCDC 2095098'
loop_
_audit_author_name
_audit_author_address
'Hatem Titi'
;McGill University
Canada
;
_audit_update_record             
;
2021-07-07 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
'(dibromomethyl)triphenylphosphonium bromide 1-isobutylaldehyde'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Br3 O0.75 P'
_chemical_formula_weight         569.09

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   33.1440(5)
_cell_length_b                   33.1440(5)
_cell_length_c                   11.4650(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     10907.2(4)
_cell_formula_units_Z            18
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4252
_cell_measurement_theta_min      5.338
_cell_measurement_theta_max      72.437

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             5040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.111
_exptl_absorpt_coefficient_mu    6.849
_shelx_estimated_absorpt_T_min   0.265
_shelx_estimated_absorpt_T_max   0.517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4015
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            74083
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         5.338
_diffrn_reflns_theta_max         72.437
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4764
_reflns_number_gt                4252
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'enCIFer 2020.2.0'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+40.0779P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.000046(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4764
_refine_ls_number_parameters     254
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.58976(3) 0.50770(3) 0.24632(6) 0.0529(2) Uani 1 1 d . . . . .
C2 C 0.61167(14) 0.46846(13) 0.2272(3) 0.0636(8) Uani 1 1 d . . . . .
C3 C 0.65903(16) 0.48626(17) 0.2121(4) 0.0823(11) Uani 1 1 d . . . . .
H3 H 0.679228 0.518262 0.215721 0.099 Uiso 1 1 calc R U . . .
C4 C 0.6765(2) 0.4568(3) 0.1916(5) 0.1136(17) Uani 1 1 d . . . . .
H4 H 0.708361 0.468716 0.181730 0.136 Uiso 1 1 calc R U . . .
C5 C 0.6470(3) 0.4107(3) 0.1862(5) 0.125(2) Uani 1 1 d . . . . .
H5 H 0.658662 0.390892 0.171923 0.150 Uiso 1 1 calc R U . . .
C6 C 0.5995(3) 0.3920(2) 0.2013(5) 0.1142(18) Uani 1 1 d . . . . .
H6 H 0.579647 0.359897 0.198241 0.137 Uiso 1 1 calc R U . . .
C7 C 0.58175(19) 0.42103(15) 0.2209(4) 0.0850(12) Uani 1 1 d . . . . .
H7 H 0.549842 0.408807 0.229872 0.102 Uiso 1 1 calc R U . . .
C8 C 0.63138(11) 0.55764(12) 0.3277(3) 0.0582(7) Uani 1 1 d . . . . .
C9 C 0.65347(15) 0.55016(16) 0.4216(3) 0.0781(10) Uani 1 1 d . . . . .
H9 H 0.648713 0.520544 0.437007 0.094 Uiso 1 1 calc R U . . .
C10 C 0.68291(16) 0.58789(19) 0.4921(4) 0.0896(13) Uani 1 1 d . . . . .
H10 H 0.697620 0.583283 0.555567 0.108 Uiso 1 1 calc R U . . .
C11 C 0.69026(15) 0.63119(18) 0.4691(4) 0.0864(12) Uani 1 1 d . . . . .
H11 H 0.710428 0.656075 0.515944 0.104 Uiso 1 1 calc R U . . .
C12 C 0.66827(13) 0.63862(14) 0.3773(4) 0.0741(10) Uani 1 1 d . . . . .
H12 H 0.673244 0.668372 0.362778 0.089 Uiso 1 1 calc R U . . .
C13 C 0.63846(12) 0.60161(12) 0.3058(3) 0.0630(8) Uani 1 1 d . . . . .
H13 H 0.623415 0.606541 0.243657 0.076 Uiso 1 1 calc R U . . .
C14 C 0.53518(12) 0.47912(12) 0.3228(3) 0.0632(8) Uani 1 1 d . . . . .
C15 C 0.53225(17) 0.45388(14) 0.4226(4) 0.0849(12) Uani 1 1 d . . . . .
H15 H 0.557584 0.451244 0.447084 0.102 Uiso 1 1 calc R U . . .
C16 C 0.4900(2) 0.43232(15) 0.4861(4) 0.1028(16) Uani 1 1 d . . . . .
H16 H 0.487249 0.415514 0.553474 0.123 Uiso 1 1 calc R U . . .
C17 C 0.45326(19) 0.43645(17) 0.4474(5) 0.1038(16) Uani 1 1 d . U . . .
H17 H 0.425207 0.421445 0.487871 0.125 Uiso 1 1 calc R U . . .
C18 C 0.45661(16) 0.46177(18) 0.3518(5) 0.1019(15) Uani 1 1 d . . . . .
H18 H 0.431237 0.464525 0.328291 0.122 Uiso 1 1 calc R U . . .
C19 C 0.49769(14) 0.48361(15) 0.2887(4) 0.0803(11) Uani 1 1 d . . . . .
H19 H 0.500034 0.501307 0.223450 0.096 Uiso 1 1 calc R U . . .
C20 C 0.57998(11) 0.52546(11) 0.1043(3) 0.0542(7) Uani 1 1 d . . . . .
H20 H 0.567221 0.546242 0.115229 0.065 Uiso 1 1 calc R U . . .
Br21 Br 0.63778(2) 0.55830(2) 0.01641(3) 0.06392(14) Uani 1 1 d . . . . .
Br22 Br 0.53504(2) 0.47063(2) 0.01750(3) 0.06559(15) Uani 1 1 d . . . . .
Br23 Br 0.54600(2) 0.61090(2) 0.14881(4) 0.08778(18) Uani 1 1 d . . . . .
O1A O 0.3670(3) 0.5451(3) 0.4280(6) 0.170(3) Uani 0.75 1 d . U P . .
C2A C 0.3509(6) 0.5249(5) 0.3313(10) 0.187(4) Uani 0.75 1 d . U P . .
H2A H 0.319114 0.503925 0.326996 0.224 Uiso 0.75 1 calc R U P . .
C3A C 0.3756(5) 0.5312(5) 0.2375(9) 0.179(4) Uani 0.75 1 d . U P . .
H3A H 0.372058 0.500915 0.216213 0.215 Uiso 0.75 1 calc R U P . .
C4A C 0.4206(6) 0.5589(7) 0.2735(13) 0.240(6) Uani 0.75 1 d . U P . .
H4AA H 0.440328 0.549467 0.235082 0.360 Uiso 0.75 1 calc R U P . .
H4AB H 0.422443 0.555924 0.356367 0.360 Uiso 0.75 1 calc R U P . .
H4AC H 0.430734 0.590752 0.254396 0.360 Uiso 0.75 1 calc R U P . .
C5A C 0.3663(5) 0.5500(5) 0.1341(10) 0.183(4) Uani 0.75 1 d . U P . .
H5AA H 0.366458 0.578277 0.153516 0.274 Uiso 0.75 1 calc R U P . .
H5AB H 0.336328 0.527795 0.103281 0.274 Uiso 0.75 1 calc R U P . .
H5AC H 0.389850 0.556513 0.076641 0.274 Uiso 0.75 1 calc R U P . .


_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 C2 1.792(4) . ?
P1 C14 1.796(3) . ?
P1 C8 1.797(3) . ?
P1 C20 1.815(3) . ?
C2 C7 1.379(6) . ?
C2 C3 1.384(6) . ?
C3 C4 1.383(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.340(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.378(5) . ?
C8 C9 1.392(5) . ?
C9 C10 1.397(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.356(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.393(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.380(6) . ?
C14 C15 1.392(6) . ?
C15 C16 1.415(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.351(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 Br21 1.945(3) . ?
C20 Br22 1.951(3) . ?
C20 H20 0.9800 . ?
O1A C2A 1.266(13) . ?
C2A C3A 1.305(16) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.367(18) . ?
C3A C5A 1.444(16) . ?
C3A H3A 0.9800 . ?
C4A H4AA 0.9600 . ?
C4A H4AB 0.9600 . ?
C4A H4AC 0.9600 . ?
C5A H5AA 0.9600 . ?
C5A H5AB 0.9600 . ?
C5A H5AC 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
C2 P1 C14 110.10(17) . . ?
C2 P1 C8 109.19(17) . . ?
C14 P1 C8 109.82(15) . . ?
C2 P1 C20 109.19(15) . . ?
C14 P1 C20 108.25(17) . . ?
C8 P1 C20 110.28(15) . . ?
C7 C2 C3 119.7(4) . . ?
C7 C2 P1 120.8(3) . . ?
C3 C2 P1 119.4(3) . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.1(6) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.7(6) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 119.6(6) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C2 119.5(5) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
C13 C8 C9 120.2(3) . . ?
C13 C8 P1 121.7(3) . . ?
C9 C8 P1 117.9(3) . . ?
C8 C9 C10 118.8(4) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 120.0(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 119.6(4) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C19 C14 C15 120.1(4) . . ?
C19 C14 P1 121.9(3) . . ?
C15 C14 P1 117.9(3) . . ?
C14 C15 C16 118.7(5) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 119.3(5) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C16 121.7(5) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 120.2(6) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.0(5) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
P1 C20 Br21 111.15(17) . . ?
P1 C20 Br22 109.43(16) . . ?
Br21 C20 Br22 109.67(15) . . ?
P1 C20 H20 108.9 . . ?
Br21 C20 H20 108.9 . . ?
Br22 C20 H20 108.9 . . ?
O1A C2A C3A 125.0(15) . . ?
O1A C2A H2A 117.5 . . ?
C3A C2A H2A 117.5 . . ?
C2A C3A C4A 104.2(12) . . ?
C2A C3A C5A 119.6(14) . . ?
C4A C3A C5A 110.8(15) . . ?
C2A C3A H3A 107.2 . . ?
C4A C3A H3A 107.2 . . ?
C5A C3A H3A 107.2 . . ?
C3A C4A H4AA 109.5 . . ?
C3A C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
C3A C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C3A C5A H5AA 109.5 . . ?
C3A C5A H5AB 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
C3A C5A H5AC 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?

_refine_diff_density_max         0.712
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.060


