#------------------------------------------------------------------------------
#$Date: 2024-02-04 13:26:31 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289397 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/04/1570407.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_1570407
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            'C19 H16 Cl3 P'
_chemical_formula_weight         381.64
_chemical_name_systematic        '(dichloromethyl)triphenylphosphonium chloride'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_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                90
_cell_formula_units_Z            4
_cell_length_a                   12.2883(2)
_cell_length_b                   12.5399(2)
_cell_length_c                   12.1077(2)
_cell_measurement_reflns_used    1554
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.348
_cell_measurement_theta_min      5.078
_cell_volume                     1865.72(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 0.997
_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  0.0645
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33961
_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         72.348
_diffrn_reflns_theta_min         5.078
_exptl_absorpt_coefficient_mu    5.214
_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    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0295P)²+2.1234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1554
_reflns_number_total             1936
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc04615f2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 1570391--1570408.cif.'
_cod_database_code               1570407
_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   0.576
_shelx_estimated_absorpt_t_max   0.718
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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 0.52824(7) 0.750000 0.39114(7) 0.0373(2) Uani 1 2 d S T P . .
C2 C 0.56416(19) 0.63174(18) 0.31616(19) 0.0405(5) Uani 1 1 d . . . . .
C3 C 0.4944(2) 0.5965(2) 0.2332(2) 0.0518(6) Uani 1 1 d . . . . .
H3 H 0.430164 0.632986 0.218103 0.062 Uiso 1 1 calc R U . . .
C5 C 0.6163(3) 0.4520(2) 0.1956(2) 0.0642(8) Uani 1 1 d . . . . .
H5 H 0.632998 0.390405 0.156391 0.077 Uiso 1 1 calc R U . . .
C4 C 0.5221(3) 0.5063(2) 0.1737(2) 0.0631(8) Uani 1 1 d . . . . .
H4 H 0.476125 0.482232 0.117973 0.076 Uiso 1 1 calc R U . . .
C7 C 0.6616(2) 0.5786(2) 0.3361(2) 0.0507(6) Uani 1 1 d . . . . .
H7 H 0.709603 0.603355 0.389625 0.061 Uiso 1 1 calc R U . . .
C8 C 0.3860(3) 0.750000 0.4237(3) 0.0452(8) Uani 1 2 d S T P . .
C9 C 0.3324(2) 0.6546(2) 0.4411(2) 0.0570(7) Uani 1 1 d . . . . .
H9 H 0.368933 0.590360 0.431169 0.068 Uiso 1 1 calc R U . . .
C6 C 0.6860(3) 0.4884(2) 0.2754(2) 0.0616(7) Uani 1 1 d . . . . .
H6 H 0.750610 0.452024 0.288834 0.074 Uiso 1 1 calc R U . . .
C10 C 0.2245(2) 0.6547(3) 0.4734(3) 0.0732(9) Uani 1 1 d . . . . .
H10 H 0.188228 0.590696 0.485541 0.088 Uiso 1 1 calc R U . . .
C11 C 0.1713(3) 0.750000 0.4874(4) 0.0775(15) Uani 1 2 d S T P . .
H11 H 0.098000 0.750001 0.506644 0.093 Uiso 1 2 calc R U P . .
C12 C 0.6046(3) 0.750000 0.5214(3) 0.0402(7) Uani 1 2 d S T P . .
H12 H 0.682731 0.749999 0.505396 0.048 Uiso 1 2 calc R U P . .
Cl13 Cl 0.57140(6) 0.86510(5) 0.59858(6) 0.0603(2) Uani 1 1 d . . . . .
Cl14 Cl 0.86640(7) 0.750000 0.47788(8) 0.0552(3) Uani 1 2 d S T P . .
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'
Cl Cl 0.3639 0.7018 '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 C2 110.56(10) . . ?
C8 P1 C2 110.56(10) . 7_575 ?
C2 P1 C2 111.52(15) . 7_575 ?
C8 P1 C12 108.04(16) . . ?
C2 P1 C12 108.01(9) . . ?
C2 P1 C12 108.01(9) 7_575 . ?
C7 C2 C3 120.2(2) . . ?
C7 C2 P1 121.34(18) . . ?
C3 C2 P1 118.40(19) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C7 C2 119.1(3) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C9 C8 C9 120.0(3) . 7_575 ?
C9 C8 P1 119.89(17) . . ?
C9 C8 P1 119.89(17) 7_575 . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C10 121.0(4) 7_575 . ?
C10 C11 H11 119.5 7_575 . ?
C10 C11 H11 119.5 . . ?
Cl13 C12 Cl13 109.54(17) 7_575 . ?
Cl13 C12 P1 109.67(13) 7_575 . ?
Cl13 C12 P1 109.67(13) . . ?
Cl13 C12 H12 109.3 7_575 . ?
Cl13 C12 H12 109.3 . . ?
P1 C12 H12 109.3 . . ?
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 C8 1.792(3) . ?
P1 C2 1.794(2) . ?
P1 C2 1.794(2) 7_575 ?
P1 C12 1.835(3) . ?
C2 C7 1.391(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C5 C6 1.369(4) . ?
C5 C4 1.369(4) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C7 C6 1.381(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(3) . ?
C8 C9 1.382(3) 7_575 ?
C9 C10 1.382(4) . ?
C9 H9 0.9300 . ?
C6 H6 0.9300 . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 Cl13 1.7670(19) 7_575 ?
C12 Cl13 1.7670(19) . ?
C12 H12 0.9800 . ?
