#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:26:31 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289397 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/03/1570397.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_1570397
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            'C24 H25 Br3 N O P'
_chemical_formula_weight         614.15
_chemical_name_systematic
'(dibromomethyl)triphenylphosphonium bromide N-Methylpyrrolidone 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                   33.612(2)
_cell_length_b                   33.612(2)
_cell_length_c                   11.4292(7)
_cell_measurement_reflns_used    3388
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.170
_cell_measurement_theta_min      2.629
_cell_volume                     11182.4(12)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0943
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            76439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.170
_diffrn_reflns_theta_min         2.629
_exptl_absorpt_coefficient_mu    6.750
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             5472
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4907
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0419
_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)+(0.0484P)²+70.9250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3388
_reflns_number_total             4907
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04615f2.cif
_cod_data_source_block           1_NMP
_cod_depositor_comments
'Adding full bibliography for 1570391--1570408.cif.'
_cod_original_cell_volume        11182.4(17)
_cod_database_code               1570397
_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   0.209
_shelx_estimated_absorpt_t_max   0.844
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 0.84218(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 . . . . .
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
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 . . ?
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 . ?
