#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:26:31 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289397 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/03/1570399.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_1570399
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 H23 Br3 N O P'
_chemical_formula_weight         588.11
_chemical_name_systematic
'(dibromomethyl)triphenylphosphonium bromide dimethylformamide 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                   33.1823(9)
_cell_length_b                   33.1823(9)
_cell_length_c                   11.4506(3)
_cell_measurement_reflns_used    3984
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.609
_cell_measurement_theta_min      2.663
_cell_volume                     10918.7(5)
_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 0.996
_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  0.0540
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            74379
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.609
_diffrn_reflns_theta_min         2.663
_exptl_absorpt_coefficient_mu    6.883
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             5220
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4798
_refine_ls_number_restraints     335
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0445
_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)+(0.0607P)²+56.2572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1319
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3981
_reflns_number_total             4798
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04615f2.cif
_cod_data_source_block           1-DMF
_cod_depositor_comments
'Adding full bibliography for 1570391--1570408.cif.'
_cod_original_cell_volume        10918.7(7)
_cod_database_code               1570399
_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   0.182
_shelx_estimated_absorpt_t_max   0.529
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 0.15888(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 . . .
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'
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 . . ?
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 . ?
