#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:26:31 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289397 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/04/1570403.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_1570403
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 I3 N O2 P'
_chemical_formula_weight         717.03
_chemical_name_systematic
'(diiodomethyl)(triphenyl)phosphanium iodide 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
;
2021-11-26 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            18
_cell_length_a                   32.9862(15)
_cell_length_b                   32.9862(15)
_cell_length_c                   12.0449(8)
_cell_measurement_reflns_used    3197
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.065
_cell_measurement_theta_min      2.679
_cell_volume                     11350.1(10)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1053
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23348
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.065
_diffrn_reflns_theta_min         2.679
_exptl_absorpt_coefficient_mu    29.905
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.0660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             6048
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.134
_refine_diff_density_max         3.722
_refine_diff_density_min         -1.509
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4966
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0599
_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)+(0.0822P)²+126.4434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1826
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3197
_reflns_number_total             4966
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04615f2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 1570391--1570408.cif.'
_cod_original_cell_volume        11350.1(13)
_cod_database_code               1570403
_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   0.044
_shelx_estimated_absorpt_t_max   0.108
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 0.49989(9) 0.41704(9) 0.7530(2) 0.0503(6) Uani 1 1 d . . . . .
C2 C 0.5277(4) 0.4703(4) 0.8327(9) 0.055(3) Uani 1 1 d . . . . .
I003 I 0.62354(3) 0.55236(4) 0.35346(8) 0.0815(3) Uani 1 1 d . . . . .
C3 C 0.5208(5) 0.5085(5) 0.8052(12) 0.070(3) Uani 1 1 d . . . . .
H3 H 0.503066 0.506971 0.743648 0.084 Uiso 1 1 calc R U . . .
C4 C 0.5410(5) 0.5477(5) 0.8720(13) 0.080(4) Uani 1 1 d . . . . .
H4 H 0.536633 0.572768 0.854463 0.096 Uiso 1 1 calc R U . . .
C5 C 0.5671(5) 0.5509(5) 0.9628(14) 0.087(5) Uani 1 1 d . . . . .
H5 H 0.580554 0.577921 1.005963 0.105 Uiso 1 1 calc R U . . .
C6 C 0.5733(5) 0.5141(6) 0.9902(13) 0.083(5) Uani 1 1 d . . . . .
H6 H 0.590811 0.516049 1.052437 0.100 Uiso 1 1 calc R U . . .
C7 C 0.5535(4) 0.4739(5) 0.9256(12) 0.073(4) Uani 1 1 d . . . . .
H7 H 0.557867 0.449081 0.945298 0.088 Uiso 1 1 calc R U . . .
C8 C 0.5407(4) 0.3969(4) 0.7340(10) 0.057(3) Uani 1 1 d . . . . .
C9 C 0.5879(5) 0.4276(6) 0.7236(12) 0.077(4) Uani 1 1 d . . . . .
H9 H 0.599764 0.459578 0.732087 0.092 Uiso 1 1 calc R U . . .
C10 C 0.6174(6) 0.4102(7) 0.7004(15) 0.095(5) Uani 1 1 d . . . . .
H10 H 0.649525 0.430572 0.697996 0.115 Uiso 1 1 calc R U . . .
C11 C 0.5997(7) 0.3623(8) 0.6805(18) 0.115(7) Uani 1 1 d . . . . .
H11 H 0.619522 0.351169 0.659947 0.138 Uiso 1 1 calc R U . . .
C12 C 0.5528(7) 0.3326(7) 0.6918(16) 0.103(5) Uani 1 1 d . . . . .
H12 H 0.540747 0.300615 0.682193 0.124 Uiso 1 1 calc R U . . .
C13 C 0.5234(5) 0.3489(5) 0.7170(12) 0.074(4) Uani 1 1 d . . . . .
H13 H 0.491487 0.328050 0.723008 0.089 Uiso 1 1 calc R U . . .
C14 C 0.4506(4) 0.3745(4) 0.8292(10) 0.055(3) Uani 1 1 d . . . . .
C15 C 0.4584(5) 0.3558(4) 0.9264(10) 0.064(3) Uani 1 1 d . . . . .
H15 H 0.488664 0.363198 0.945662 0.077 Uiso 1 1 calc R U . . .
C16 C 0.4215(6) 0.3266(4) 0.9929(11) 0.071(4) Uani 1 1 d . . . . .
H16 H 0.426873 0.314995 1.058097 0.085 Uiso 1 1 calc R U . . .
C17 C 0.3763(5) 0.3144(4) 0.9638(11) 0.070(4) Uani 1 1 d . . . . .
H17 H 0.351440 0.293766 1.008267 0.083 Uiso 1 1 calc R U . . .
C18 C 0.3679(5) 0.3321(4) 0.8710(11) 0.069(3) Uani 1 1 d . . . . .
H18 H 0.337356 0.324116 0.852924 0.083 Uiso 1 1 calc R U . . .
C19 C 0.4045(4) 0.3622(4) 0.8029(11) 0.059(3) Uani 1 1 d . . . . .
H19 H 0.398385 0.374191 0.739223 0.071 Uiso 1 1 calc R U . . .
C20 C 0.4830(4) 0.4287(4) 0.6221(9) 0.053(2) Uani 1 1 d . . . . .
H20 H 0.462524 0.441884 0.634577 0.063 Uiso 1 1 calc R U . . .
I21 I 0.44653(3) 0.36721(3) 0.51635(6) 0.0586(2) Uani 1 1 d . . . . .
I22 I 0.54390(3) 0.47887(3) 0.52696(6) 0.0619(2) Uani 1 1 d . . . . .
C23 C 0.4897(10) 0.2169(10) 0.365(2) 0.152(9) Uani 1 1 d G U . . .
H23A H 0.513671 0.225361 0.309924 0.228 Uiso 1 1 calc R U . . .
H23B H 0.473730 0.234140 0.351957 0.228 Uiso 1 1 calc R U . . .
H23C H 0.467737 0.184000 0.360263 0.228 Uiso 1 1 calc R U . . .
N24 N 0.5107(10) 0.2280(9) 0.474(2) 0.154(6) Uani 1 1 d . U . . .
O25 O 0.5548(10) 0.2561(10) 0.466(2) 0.224(10) Uani 1 1 d . U . . .
O26 O 0.4936(7) 0.2179(7) 0.5576(15) 0.155(6) 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'
I I -0.3257 6.8362 '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
C20 P1 C14 111.5(5) . . ?
C20 P1 C8 110.1(6) . . ?
C14 P1 C8 109.4(5) . . ?
C20 P1 C2 108.9(5) . . ?
C14 P1 C2 108.2(5) . . ?
C8 P1 C2 108.7(5) . . ?
C7 C2 C3 118.5(12) . . ?
C7 C2 P1 120.7(10) . . ?
C3 C2 P1 120.7(10) . . ?
C4 C3 C2 118.6(15) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C5 C4 C3 122.0(16) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 119.6(12) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 120.4(16) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 120.9(16) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C13 119.4(13) . . ?
C9 C8 P1 121.5(11) . . ?
C13 C8 P1 118.8(9) . . ?
C8 C9 C10 119.0(16) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C10 C11 121.2(16) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 118.4(15) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C13 C12 C11 121.0(18) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 120.8(15) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C19 C14 C15 118.2(11) . . ?
C19 C14 P1 122.9(9) . . ?
C15 C14 P1 118.7(10) . . ?
C16 C15 C14 120.0(13) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.5(13) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.6(12) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.3(14) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.4(12) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
P1 C20 I21 113.9(5) . . ?
P1 C20 I22 111.1(5) . . ?
I21 C20 I22 105.6(5) . . ?
P1 C20 H20 108.7 . . ?
I21 C20 H20 108.7 . . ?
I22 C20 H20 108.7 . . ?
N24 C23 H23A 109.5 . . ?
N24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O26 N24 O25 120(3) . . ?
O26 N24 C23 130(3) . . ?
O25 N24 C23 110(3) . . ?
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 C20 1.777(12) . ?
P1 C14 1.782(12) . ?
P1 C8 1.790(13) . ?
P1 C2 1.799(11) . ?
C2 C7 1.375(19) . ?
C2 C3 1.427(19) . ?
C3 C4 1.380(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.36(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.37(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.387(19) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.373(18) . ?
C8 C13 1.402(19) . ?
C9 C10 1.38(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.40(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.36(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.36(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.401(18) . ?
C14 C15 1.407(17) . ?
C15 C16 1.371(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.38(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.35(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(17) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 I21 2.178(11) . ?
C20 I22 2.183(10) . ?
C20 H20 0.9800 . ?
C23 N24 1.45(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
N24 O26 1.12(3) . ?
N24 O25 1.28(3) . ?
