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#$Date: 2024-02-04 13:26:31 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289397 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/03/1570391.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_1570391
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            'C19 H16 Br3 P'
_chemical_formula_weight         515.02
_chemical_name_systematic        '(dibromomethyl)(triphenyl)phosphanium bromide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-11-26 deposited with the CCDC.	2023-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.2280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.7546(4)
_cell_length_b                   15.5320(3)
_cell_length_c                   28.3321(6)
_cell_measurement_reflns_used    6372
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.294
_cell_measurement_theta_min      3.160
_cell_volume                     7711.9(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      180(2)
_diffrn_measured_fraction_theta_full 1.000
_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  0.0643
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            67258
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.294
_diffrn_reflns_theta_min         3.160
_exptl_absorpt_coefficient_mu    8.506
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             4000
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7620
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0328
_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)+(0.0466P)²+15.9340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0878
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6372
_reflns_number_total             7620
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04615f2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 1570391--1570408.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1570391
_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   0.676
_shelx_estimated_absorpt_t_max   0.848
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'
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 . . . . .
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'
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) . . ?
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) . ?
