#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:26:31 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289397 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/04/1570402.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1570402
loop_
_publ_author_name
'Marrett, Joseph M.'
'Titi, Hatem M.'
'Teoh, Yong'
'Friščić, Tomislav'
_publ_section_title
;
 Supramolecular "baking powder": a hexameric halogen-bonded phosphonium
 salt cage encapsulates and functionalises small-molecule carbonyl
 compounds.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              298
_journal_page_last               306
_journal_paper_doi               10.1039/d2sc04615f
_journal_volume                  15
_journal_year                    2023
_chemical_formula_sum            'C22 H22 Br3 O P'
_chemical_formula_weight         573.09
_chemical_name_systematic
'(dibromomethyl)triphenylphosphonium bromide acetone solvate'
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-07-07 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   33.0003(6)
_cell_length_b                   33.0003(6)
_cell_length_c                   11.1350(2)
_cell_measurement_reflns_used    4042
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.396
_cell_measurement_theta_min      4.261
_cell_volume                     10501.6(3)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_publication_material  'enCIFer 2020.2.0'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            58815
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.396
_diffrn_reflns_theta_min         4.261
_exptl_absorpt_coefficient_mu    7.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5076
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.097
_exptl_transmission_factor_max   0.7536
_exptl_transmission_factor_min   0.4680
_refine_diff_density_max         1.444
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4613
_refine_ls_number_restraints     253
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0226P)²+61.3818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0711
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4042
_reflns_number_total             4613
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04615f2.cif
_cod_data_source_block           1_acetone
_cod_depositor_comments
'Adding full bibliography for 1570391--1570408.cif.'
_cod_original_cell_volume        10501.6(4)
_cod_database_code               1570402
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.274
_shelx_estimated_absorpt_t_max   0.545
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'
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 0.50588(3) 0.59196(2) 0.24976(6) 0.02638(15) Uani 1 1 d . . . . .
C2 C 0.47635(10) 0.53817(11) 0.1668(3) 0.0328(6) Uani 1 1 d . . . . .
C3 C 0.47880(12) 0.49889(12) 0.1995(3) 0.0439(8) Uani 1 1 d . . . . .
H3 H 0.495447 0.499333 0.267356 0.053 Uiso 1 1 calc R U . . .
C5 C 0.43197(14) 0.45854(16) 0.0278(4) 0.0668(13) Uani 1 1 d . . . . .
H5 H 0.416579 0.431463 -0.018245 0.080 Uiso 1 1 calc R U . . .
C4 C 0.45590(15) 0.45878(13) 0.1290(4) 0.0611(11) Uani 1 1 d . . . . .
H4 H 0.456803 0.432017 0.150567 0.073 Uiso 1 1 calc R U . . .
C9 C 0.60000(11) 0.64123(11) 0.1846(3) 0.0341(6) Uani 1 1 d . . . . .
H9 H 0.605566 0.626315 0.247970 0.041 Uiso 1 1 calc R U . . .
C6 C 0.43051(13) 0.49769(17) -0.0063(4) 0.0606(11) Uani 1 1 d . . . . .
H6 H 0.414863 0.497306 -0.076101 0.073 Uiso 1 1 calc R U . . .
C7 C 0.45233(12) 0.53791(14) 0.0634(3) 0.0457(8) Uani 1 1 d . . . . .
H7 H 0.450962 0.564393 0.041354 0.055 Uiso 1 1 calc R U . . .
C8 C 0.55534(10) 0.63416(10) 0.1649(2) 0.0294(6) Uani 1 1 d . . . . .
C10 C 0.63635(12) 0.67084(12) 0.1085(3) 0.0413(7) Uani 1 1 d . . . . .
H10 H 0.666391 0.675904 0.121122 0.050 Uiso 1 1 calc R U . . .
C11 C 0.62769(14) 0.69272(12) 0.0140(3) 0.0469(8) Uani 1 1 d . . . . .
H11 H 0.652059 0.712479 -0.036547 0.056 Uiso 1 1 calc R U . . .
C12 C 0.58336(14) 0.68558(13) -0.0059(3) 0.0486(9) Uani 1 1 d . . . . .
H12 H 0.577941 0.700346 -0.069924 0.058 Uiso 1 1 calc R U . . .
C13 C 0.54700(13) 0.65650(12) 0.0691(3) 0.0401(7) Uani 1 1 d . . . . .
H13 H 0.517111 0.651784 0.056054 0.048 Uiso 1 1 calc R U . . .
C14 C 0.46611(11) 0.61336(11) 0.2750(3) 0.0331(6) Uani 1 1 d . . . . .
C15 C 0.48398(13) 0.66118(12) 0.2947(3) 0.0435(8) Uani 1 1 d . . . . .
H15 H 0.516013 0.681899 0.290124 0.052 Uiso 1 1 calc R U . . .
C16 C 0.45371(17) 0.67739(16) 0.3210(4) 0.0623(11) Uani 1 1 d . . . . .
H16 H 0.465340 0.709160 0.333908 0.075 Uiso 1 1 calc R U . . .
C17 C 0.40661(18) 0.64679(19) 0.3281(4) 0.0687(12) Uani 1 1 d . . . . .
H17 H 0.386426 0.657975 0.345880 0.082 Uiso 1 1 calc R U . . .
C18 C 0.38882(15) 0.59981(18) 0.3094(4) 0.0623(11) Uani 1 1 d . . . . .
H18 H 0.356719 0.579448 0.314214 0.075 Uiso 1 1 calc R U . . .
C19 C 0.41843(12) 0.58247(14) 0.2833(3) 0.0456(8) Uani 1 1 d . . . . .
H19 H 0.406440 0.550583 0.271479 0.055 Uiso 1 1 calc R U . . .
C20 C 0.52514(10) 0.58131(10) 0.3933(2) 0.0291(6) Uani 1 1 d . . . . .
H20 H 0.545843 0.568507 0.378727 0.035 Uiso 1 1 calc R U . . .
Br21 Br 0.55934(2) 0.63953(2) 0.48285(3) 0.03204(9) Uani 1 1 d . . . . .
Br22 Br 0.47120(2) 0.53615(2) 0.48557(3) 0.03318(9) Uani 1 1 d . . . . .
Br23 Br 0.60346(2) 0.72674(2) 0.67057(3) 0.03998(10) Uani 1 1 d . . . . .
O1A O 0.29701(17) 0.51512(19) 0.4380(5) 0.0833(18) Uani 0.755(8) 1 d G U P A 1
C2A C 0.3023(2) 0.5060(2) 0.5353(5) 0.086(2) Uani 0.755(8) 1 d G U P A 1
C3A C 0.3415(4) 0.5357(4) 0.6225(9) 0.161(5) Uani 0.755(8) 1 d G U P A 1
H3AA H 0.361068 0.522115 0.633083 0.241 Uiso 0.755(8) 1 calc R U P A 1
H3AB H 0.328367 0.536883 0.698443 0.241 Uiso 0.755(8) 1 calc R U P A 1
H3AC H 0.359772 0.566782 0.590953 0.241 Uiso 0.755(8) 1 calc R U P A 1
C4A C 0.2753(3) 0.4581(4) 0.5681(8) 0.110(3) Uani 0.755(8) 1 d . U P A 1
H4AA H 0.254593 0.440727 0.503504 0.165 Uiso 0.755(8) 1 calc R U P A 1
H4AB H 0.257311 0.455156 0.638680 0.165 Uiso 0.755(8) 1 calc R U P A 1
H4AC H 0.295805 0.445935 0.584439 0.165 Uiso 0.755(8) 1 calc R U P A 1
O1B O 0.3013(6) 0.5429(7) 0.5124(17) 0.099(5) Uani 0.245(8) 1 d DG U P A 2
C2B C 0.2946(6) 0.5121(6) 0.5821(16) 0.086(2) Uani 0.245(8) 1 d DG U P A 2
C3B C 0.2533(12) 0.4630(7) 0.577(3) 0.157(12) Uani 0.245(8) 1 d DG U P A 2
H3BA H 0.225128 0.463632 0.594055 0.236 Uiso 0.245(8) 1 calc R U P A 2
H3BB H 0.257263 0.443755 0.634933 0.236 Uiso 0.245(8) 1 calc R U P A 2
H3BC H 0.251181 0.450288 0.497920 0.236 Uiso 0.245(8) 1 calc R U P A 2
C4B C 0.3137(9) 0.5262(9) 0.7063(18) 0.110(3) Uani 0.245(8) 1 d D U P A 2
H4BA H 0.314654 0.500664 0.744809 0.165 Uiso 0.245(8) 1 calc R U P A 2
H4BB H 0.293957 0.534252 0.751431 0.165 Uiso 0.245(8) 1 calc R U P A 2
H4BC H 0.344742 0.552749 0.702306 0.165 Uiso 0.245(8) 1 calc R U P A 2
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'
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 C2 109.23(13) . . ?
C8 P1 C14 109.70(15) . . ?
C2 P1 C14 109.08(15) . . ?
C8 P1 C20 110.03(14) . . ?
C2 P1 C20 109.31(14) . . ?
C14 P1 C20 109.48(13) . . ?
C3 C2 C7 120.6(3) . . ?
C3 C2 P1 122.2(3) . . ?
C7 C2 P1 117.2(3) . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 119.2(4) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C9 C8 C13 120.2(3) . . ?
C9 C8 P1 121.6(2) . . ?
C13 C8 P1 117.9(2) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C19 C14 C15 120.2(3) . . ?
C19 C14 P1 120.4(3) . . ?
C15 C14 P1 119.3(3) . . ?
C16 C15 C14 119.5(4) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.8(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.0(4) . . ?
C14 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
P1 C20 Br21 110.24(15) . . ?
P1 C20 Br22 109.74(15) . . ?
Br21 C20 Br22 109.98(13) . . ?
P1 C20 H20 109.0 . . ?
Br21 C20 H20 109.0 . . ?
Br22 C20 H20 109.0 . . ?
O1A C2A C4A 115.9(6) . . ?
O1A C2A C3A 128.2 . . ?
C4A C2A C3A 114.2(6) . . ?
C2A C3A H3AA 109.5 . . ?
C2A C3A H3AB 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
C2A C3A H3AC 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C2A C4A H4AA 109.5 . . ?
C2A C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
C2A C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
O1B C2B C4B 117.4(14) . . ?
O1B C2B C3B 124.3 . . ?
C4B C2B C3B 112.7(8) . . ?
C2B C3B H3BA 109.5 . . ?
C2B C3B H3BB 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
C2B C3B H3BC 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
C2B C4B H4BA 109.5 . . ?
C2B C4B H4BB 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
C2B C4B H4BC 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
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 1.796(3) . ?
P1 C2 1.796(3) . ?
P1 C14 1.796(3) . ?
P1 C20 1.818(3) . ?
C2 C3 1.387(5) . ?
C2 C7 1.396(5) . ?
C3 C4 1.392(5) . ?
C3 H3 0.9300 . ?
C5 C6 1.370(7) . ?
C5 C4 1.374(7) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C9 C8 1.389(4) . ?
C9 C10 1.393(4) . ?
C9 H9 0.9300 . ?
C6 C7 1.388(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.400(4) . ?
C10 C11 1.384(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.385(5) . ?
C14 C15 1.399(5) . ?
C15 C16 1.380(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 Br21 1.947(3) . ?
C20 Br22 1.948(3) . ?
C20 H20 0.9800 . ?
O1A C2A 1.1607 . ?
C2A C4A 1.421(11) . ?
C2A C3A 1.5193 . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C4A H4AA 0.9600 . ?
C4A H4AB 0.9600 . ?
C4A H4AC 0.9600 . ?
O1B C2B 1.2103 . ?
C2B C4B 1.493(14) . ?
C2B C3B 1.5099 . ?
C3B H3BA 0.9600 . ?
C3B H3BB 0.9600 . ?
C3B H3BC 0.9600 . ?
C4B H4BA 0.9600 . ?
C4B H4BB 0.9600 . ?
C4B H4BC 0.9600 . ?
