#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:26:31 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289397 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/04/1570404.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_1570404
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            'C42 H41 Br6 O P2'
_chemical_formula_weight         1103.15
_chemical_name_systematic
'(dibromomethyl)triphenylphosphonium bromide 1-proprionaldehyde'
_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
;
2021-11-26 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            9
_cell_length_a                   32.8602(12)
_cell_length_b                   32.8602(12)
_cell_length_c                   11.2660(4)
_cell_measurement_reflns_used    3721
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.343
_cell_measurement_theta_min      4.661
_cell_volume                     10535.2(7)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0644
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            25610
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.343
_diffrn_reflns_theta_min         4.661
_exptl_absorpt_coefficient_mu    7.062
_exptl_absorpt_correction_T_max  0.7249
_exptl_absorpt_correction_T_min  0.7144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4869
_exptl_crystal_size_max          0.648
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.118
_refine_diff_density_max         1.611
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.133
_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     244
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     221
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1108P)²+33.6233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3721
_reflns_number_total             4601
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04615f2.cif
_cod_data_source_block           1_propionaldehyde
_cod_depositor_comments
'Adding full bibliography for 1570391--1570408.cif.'
_cod_original_cell_volume        10535.1(9)
_cod_database_code               1570404
_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   0.092
_shelx_estimated_absorpt_t_max   0.490
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 0.83853(4) 0.58323(4) 0.42187(10) 0.0462(3) Uani 1 1 d . . . . .
C2 C 0.81009(17) 0.60941(19) 0.3431(4) 0.0541(11) Uani 1 1 d . . . . .
C3 C 0.8157(2) 0.6526(2) 0.3773(6) 0.0665(13) Uani 1 1 d . . . . .
H3 H 0.833656 0.668327 0.443476 0.080 Uiso 1 1 calc R U . . .
C4 C 0.7939(3) 0.6718(3) 0.3101(8) 0.0875(19) Uani 1 1 d . . . . .
H4 H 0.796981 0.700419 0.332874 0.105 Uiso 1 1 calc R U . . .
C6 C 0.7635(2) 0.6083(3) 0.1778(7) 0.091(2) Uani 1 1 d . . . . .
H6 H 0.746234 0.593806 0.109874 0.110 Uiso 1 1 calc R U . . .
C5 C 0.7683(2) 0.6498(3) 0.2125(8) 0.094(2) Uani 1 1 d . . . . .
H5 H 0.753945 0.663308 0.169242 0.113 Uiso 1 1 calc R U . . .
C7 C 0.7840(2) 0.5865(3) 0.2420(5) 0.0727(15) Uani 1 1 d . . . . .
H7 H 0.780414 0.557829 0.217996 0.087 Uiso 1 1 calc R U . . .
C8 C 0.79787(19) 0.52223(19) 0.4443(5) 0.0579(11) Uani 1 1 d . . . . .
C9 C 0.8138(3) 0.4903(2) 0.4592(6) 0.0741(15) Uani 1 1 d . . . . .
H9 H 0.845702 0.500389 0.453018 0.089 Uiso 1 1 calc R U . . .
C10 C 0.7829(4) 0.4449(3) 0.4824(8) 0.104(2) Uani 1 1 d . . . . .
H10 H 0.793897 0.423896 0.492025 0.125 Uiso 1 1 calc R U . . .
C13 C 0.7503(2) 0.5064(2) 0.4543(6) 0.0750(15) Uani 1 1 d . . . . .
H13 H 0.739156 0.527281 0.445989 0.090 Uiso 1 1 calc R U . . .
C14 C 0.88783(18) 0.59032(18) 0.3376(4) 0.0517(10) Uani 1 1 d . . . . .
C15 C 0.8792(2) 0.5605(2) 0.2403(5) 0.0703(14) Uani 1 1 d . . . . .
H15 H 0.848970 0.536067 0.224788 0.084 Uiso 1 1 calc R U . . .
C16 C 0.9164(3) 0.5680(3) 0.1675(6) 0.0823(17) Uani 1 1 d . . . . .
H16 H 0.910974 0.548069 0.103517 0.099 Uiso 1 1 calc R U . . .
C17 C 0.9601(3) 0.6037(3) 0.1879(6) 0.0808(17) Uani 1 1 d . . . . .
H17 H 0.984374 0.608397 0.137119 0.097 Uiso 1 1 calc R U . . .
C18 C 0.9695(2) 0.6337(3) 0.2834(6) 0.0718(14) Uani 1 1 d . . . . .
H18 H 0.999946 0.658140 0.296942 0.086 Uiso 1 1 calc R U . . .
C19 C 0.93307(19) 0.6269(2) 0.3593(5) 0.0590(11) Uani 1 1 d . . . . .
H19 H 0.939035 0.646768 0.423865 0.071 Uiso 1 1 calc R U . . .
C20 C 0.85756(16) 0.61179(18) 0.5647(4) 0.0493(9) Uani 1 1 d . . . . .
H20 H 0.878499 0.645560 0.552441 0.059 Uiso 1 1 calc R U . . .
Br21 Br 0.80308(2) 0.60212(2) 0.65557(5) 0.0610(2) Uani 1 1 d . . . . .
Br22 Br 0.89103(2) 0.58665(2) 0.65371(5) 0.0592(2) Uani 1 1 d . . . . .
Br23 Br 0.72371(2) 0.60094(2) 0.82392(6) 0.0777(2) Uani 1 1 d . . . . .
C12 C 0.7193(3) 0.4594(3) 0.4768(8) 0.103(2) Uani 1 1 d . . . . .
H12 H 0.687125 0.448213 0.481580 0.123 Uiso 1 1 calc R U . . .
C11 C 0.7369(4) 0.4291(3) 0.4920(9) 0.117(3) Uani 1 1 d . . . . .
H11 H 0.716459 0.397567 0.509117 0.140 Uiso 1 1 calc R U . . .
O1B O 0.8311(5) 0.3824(6) 0.5973(11) 0.129(4) Uani 0.5 1 d D U P . .
C2B C 0.8388(13) 0.4062(7) 0.798(2) 0.227(10) Uani 0.5 1 d D U P . .
H1AA H 0.863538 0.426861 0.851616 0.272 Uiso 0.5 1 calc R U P . .
H1AB H 0.817549 0.418274 0.785000 0.272 Uiso 0.5 1 calc R U P . .
C1B C 0.8590(6) 0.4006(9) 0.6795(14) 0.183(8) Uani 0.5 1 d D U P . .
H0AA H 0.890781 0.410550 0.670844 0.220 Uiso 0.5 1 calc R U P . .
C3B C 0.8123(8) 0.3555(8) 0.8451(12) 0.248(8) Uani 1 1 d D U . . .
H2AA H 0.780500 0.346905 0.863356 0.372 Uiso 1 1 calc R U . . .
H2AB H 0.827585 0.353315 0.915515 0.372 Uiso 1 1 calc R U . . .
H2AC H 0.812425 0.334497 0.785814 0.372 Uiso 1 1 calc R U . . .
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 C14 110.0(2) . . ?
C8 P1 C2 109.4(3) . . ?
C14 P1 C2 109.3(2) . . ?
C8 P1 C20 109.1(2) . . ?
C14 P1 C20 110.4(2) . . ?
C2 P1 C20 108.6(2) . . ?
C3 C2 C7 120.5(5) . . ?
C3 C2 P1 121.2(4) . . ?
C7 C2 P1 118.2(5) . . ?
C4 C3 C2 118.4(7) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 121.6(8) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C5 C6 C7 121.5(7) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C5 C4 120.1(6) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C2 C7 C6 117.8(7) . . ?
C2 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C13 C8 C9 119.0(5) . . ?
C13 C8 P1 120.3(5) . . ?
C9 C8 P1 120.6(4) . . ?
C10 C9 C8 119.8(7) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 121.7(9) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C13 C8 119.9(7) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C19 C14 C15 119.9(5) . . ?
C19 C14 P1 121.8(4) . . ?
C15 C14 P1 118.0(4) . . ?
C16 C15 C14 119.1(6) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C15 121.0(6) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 121.0(6) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C19 119.6(6) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 119.5(6) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
P1 C20 Br21 109.4(2) . . ?
P1 C20 Br22 111.1(2) . . ?
Br21 C20 Br22 109.1(2) . . ?
P1 C20 H20 109.1 . . ?
Br21 C20 H20 109.1 . . ?
Br22 C20 H20 109.1 . . ?
C13 C12 C11 118.9(8) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C10 C11 C12 120.6(8) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C3B C2B C1B 102.39(18) . . ?
C3B C2B H1AA 111.3 . . ?
C1B C2B H1AA 111.3 . . ?
C3B C2B H1AB 111.3 . . ?
C1B C2B H1AB 111.3 . . ?
H1AA C2B H1AB 109.2 . . ?
O1B C1B C2B 117(2) . . ?
O1B C1B H0AA 121.7 . . ?
C2B C1B H0AA 121.7 . . ?
C2B C3B H2AA 109.5 . . ?
C2B C3B H2AB 109.5 . . ?
H2AA C3B H2AB 109.5 . . ?
C2B C3B H2AC 109.5 . . ?
H2AA C3B H2AC 109.5 . . ?
H2AB C3B H2AC 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 1.786(5) . ?
P1 C14 1.790(5) . ?
P1 C2 1.791(5) . ?
P1 C20 1.810(5) . ?
C2 C3 1.392(8) . ?
C2 C7 1.397(9) . ?
C3 C4 1.391(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.354(13) . ?
C4 H4 0.9300 . ?
C6 C5 1.350(13) . ?
C6 C7 1.404(9) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C8 C13 1.384(8) . ?
C8 C9 1.398(8) . ?
C9 C10 1.346(11) . ?
C9 H9 0.9300 . ?
C10 C11 1.336(15) . ?
C10 H10 0.9300 . ?
C13 C12 1.384(10) . ?
C13 H13 0.9300 . ?
C14 C19 1.389(8) . ?
C14 C15 1.400(8) . ?
C15 C16 1.388(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.345(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.396(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 Br21 1.946(4) . ?
C20 Br22 1.951(5) . ?
C20 H20 0.9800 . ?
C12 C11 1.390(15) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
O1B C1B 1.229(2) . ?
C2B C3B 1.539(2) . ?
C2B C1B 1.539(2) . ?
C2B H1AA 0.9700 . ?
C2B H1AB 0.9700 . ?
C1B H0AA 0.9300 . ?
C3B H2AA 0.9600 . ?
C3B H2AB 0.9600 . ?
C3B H2AC 0.9600 . ?
