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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/1/57/03/1570392.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_1570392
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            'C20 H19 Br3 N O2 P'
_chemical_formula_weight         576.06
_chemical_name_systematic
'dibromomethyl)triphenylphosphonium bromide nitromethane 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                   32.270(2)
_cell_length_b                   32.270(2)
_cell_length_c                   11.3230(8)
_cell_measurement_reflns_used    4049
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.736
_cell_measurement_theta_min      4.213
_cell_volume                     10211.5(11)
_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 0.982
_diffrn_measured_fraction_theta_max 0.978
_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  0.0366
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17041
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.736
_diffrn_reflns_theta_min         4.213
_exptl_absorpt_coefficient_mu    7.381
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5076
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4416
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0278
_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)+(0.0116P)²+47.6886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4049
_reflns_number_total             4416
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04615f2.cif
_cod_data_source_block           1_nitromethane
_cod_depositor_comments
'Adding full bibliography for 1570391--1570408.cif.'
_cod_original_cell_volume        10211.4(15)
_cod_database_code               1570392
_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   0.352
_shelx_estimated_absorpt_t_max   0.622
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 0.16139(2) 0.41614(2) 0.57990(5) 0.02260(13) Uani 1 1 d . . . . .
C2 C 0.20277(9) 0.47856(9) 0.5579(2) 0.0286(5) Uani 1 1 d . . . . .
C3 C 0.25170(10) 0.49476(11) 0.5490(3) 0.0399(7) Uani 1 1 d . . . . .
H3 H 0.263566 0.473418 0.560726 0.048 Uiso 1 1 calc R U . . .
C4 C 0.28265(13) 0.54253(14) 0.5227(3) 0.0577(9) Uani 1 1 d . . . . .
H4 H 0.316058 0.554129 0.517375 0.069 Uiso 1 1 calc R U . . .
C5 C 0.26538(15) 0.57315(13) 0.5042(4) 0.0623(10) Uani 1 1 d . . . . .
H5 H 0.286943 0.605675 0.485106 0.075 Uiso 1 1 calc R U . . .
C6 C 0.21735(15) 0.55738(12) 0.5131(3) 0.0551(9) Uani 1 1 d . . . . .
H6 H 0.205813 0.578952 0.500571 0.066 Uiso 1 1 calc R U . . .
C7 C 0.18576(11) 0.50995(10) 0.5403(3) 0.0390(6) Uani 1 1 d . . . . .
H7 H 0.152494 0.498937 0.546929 0.047 Uiso 1 1 calc R U . . .
C8 C 0.11110(9) 0.40936(9) 0.6638(2) 0.0253(5) Uani 1 1 d . . . . .
C9 C 0.12063(10) 0.43898(10) 0.7614(2) 0.0333(6) Uani 1 1 d . . . . .
H9 H 0.152364 0.463847 0.777090 0.040 Uiso 1 1 calc R U . . .
C10 C 0.08343(12) 0.43195(12) 0.8355(3) 0.0400(7) Uani 1 1 d . . . . .
H10 H 0.089725 0.451840 0.902782 0.048 Uiso 1 1 calc R U . . .
C11 C 0.03741(11) 0.39617(12) 0.8118(3) 0.0383(7) Uani 1 1 d . . . . .
H11 H 0.011993 0.391961 0.861997 0.046 Uiso 1 1 calc R U . . .
C12 C 0.02786(10) 0.36630(11) 0.7156(3) 0.0344(6) Uani 1 1 d . . . . .
H12 H -0.003978 0.341474 0.700741 0.041 Uiso 1 1 calc R U . . .
C13 C 0.06457(9) 0.37244(10) 0.6407(2) 0.0286(5) Uani 1 1 d . . . . .
H13 H 0.058167 0.351872 0.574820 0.034 Uiso 1 1 calc R U . . .
C14 C 0.18997(9) 0.38897(10) 0.6578(2) 0.0278(5) Uani 1 1 d . . . . .
C15 C 0.18386(10) 0.34475(11) 0.6233(3) 0.0357(6) Uani 1 1 d . . . . .
H15 H 0.165367 0.328932 0.555423 0.043 Uiso 1 1 calc R U . . .
C16 C 0.20512(12) 0.32410(13) 0.6893(3) 0.0465(8) Uani 1 1 d . . . . .
H16 H 0.201351 0.294105 0.666204 0.056 Uiso 1 1 calc R U . . .
C17 C 0.23152(11) 0.34687(14) 0.7876(3) 0.0493(9) Uani 1 1 d . . . . .
H17 H 0.246375 0.332742 0.831400 0.059 Uiso 1 1 calc R U . . .
C18 C 0.23675(10) 0.38996(14) 0.8236(3) 0.0477(8) Uani 1 1 d . . . . .
H18 H 0.254500 0.404992 0.892930 0.057 Uiso 1 1 calc R U . . .
C19 C 0.21611(10) 0.41154(12) 0.7586(3) 0.0383(6) Uani 1 1 d . . . . .
H19 H 0.219849 0.441404 0.782922 0.046 Uiso 1 1 calc R U . . .
C20 C 0.14225(9) 0.38734(9) 0.4373(2) 0.0252(5) Uani 1 1 d . . . . .
H20 H 0.120642 0.352178 0.449012 0.030 Uiso 1 1 calc R U . . .
Br21 Br 0.10837(2) 0.41296(2) 0.34922(2) 0.02783(8) Uani 1 1 d . . . . .
Br22 Br 0.19849(2) 0.39808(2) 0.34814(2) 0.02884(9) Uani 1 1 d . . . . .
Br23 Br 0.27837(2) 0.40252(2) 0.17609(3) 0.04270(10) Uani 1 1 d . . . . .
C1B C 0.3791(3) 0.5407(3) 0.1792(5) 0.126(3) Uani 1 1 d . U . . .
H00I H 0.411045 0.561226 0.145899 0.189 Uiso 1 1 calc R U . . .
H00P H 0.354963 0.540506 0.126377 0.189 Uiso 1 1 calc R U . . .
H00Q H 0.373433 0.508024 0.187713 0.189 Uiso 1 1 calc R U . . .
N2B N 0.37607(19) 0.55837(17) 0.2909(4) 0.0853(12) Uani 1 1 d . U . . .
O3B O 0.3638(2) 0.5900(2) 0.2908(5) 0.1445(19) Uani 1 1 d . U . . .
O4B O 0.38227(15) 0.54551(13) 0.3811(3) 0.0878(10) Uani 1 1 d . 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 110.00(12) . . ?
C14 P1 C8 109.55(11) . . ?
C2 P1 C8 109.30(12) . . ?
C14 P1 C20 108.37(12) . . ?
C2 P1 C20 108.90(12) . . ?
C8 P1 C20 110.70(12) . . ?
C7 C2 C3 120.2(3) . . ?
C7 C2 P1 119.7(2) . . ?
C3 C2 P1 119.9(2) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C2 C7 H7 120.1 . . ?
C9 C8 C13 120.6(2) . . ?
C9 C8 P1 117.4(2) . . ?
C13 C8 P1 121.7(2) . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 118.9(3) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C19 C14 C15 120.3(3) . . ?
C19 C14 P1 118.3(2) . . ?
C15 C14 P1 121.2(2) . . ?
C16 C15 C14 119.2(3) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 119.3(3) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
P1 C20 Br21 111.05(13) . . ?
P1 C20 Br22 108.79(12) . . ?
Br21 C20 Br22 109.28(12) . . ?
P1 C20 H20 109.2 . . ?
Br21 C20 H20 109.2 . . ?
Br22 C20 H20 109.2 . . ?
N2B C1B H00I 109.5 . . ?
N2B C1B H00P 109.5 . . ?
H00I C1B H00P 109.5 . . ?
N2B C1B H00Q 109.5 . . ?
H00I C1B H00Q 109.5 . . ?
H00P C1B H00Q 109.5 . . ?
O4B N2B O3B 118.0(5) . . ?
O4B N2B C1B 125.9(5) . . ?
O3B N2B C1B 116.0(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 C14 1.791(2) . ?
P1 C2 1.792(3) . ?
P1 C8 1.797(3) . ?
P1 C20 1.811(3) . ?
C2 C7 1.387(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.391(4) . ?
C8 C13 1.398(4) . ?
C9 C10 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.389(4) . ?
C14 C15 1.396(4) . ?
C15 C16 1.389(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.371(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 Br21 1.944(2) . ?
C20 Br22 1.950(2) . ?
C20 H20 1.0000 . ?
C1B N2B 1.411(6) . ?
C1B H00I 0.9800 . ?
C1B H00P 0.9800 . ?
C1B H00Q 0.9800 . ?
N2B O4B 1.157(5) . ?
N2B O3B 1.265(6) . ?
