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#$Date: 2022-02-22 11:41:48 +0200 (Tue, 22 Feb 2022) $
#$Revision: 273090 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/45/8104586.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_8104586
loop_
_publ_author_name
'Lee, See Mun'
'Lo, Kong Mun'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of (4-methylbenzyl)(triphenyl)phosphonium chloride
 dihydrate, C26H28ClO2P
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1283
_journal_page_last               1285
_journal_paper_doi               10.1515/ncrs-2021-0305
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C26 H24 P, Cl, 2(H2 O)'
_chemical_formula_sum            'C26 H28 Cl O2 P'
_chemical_formula_weight         438.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 116.278(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6061(2)
_cell_length_b                   19.7791(4)
_cell_length_c                   11.1982(3)
_cell_measurement_reflns_used    14020
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1790
_cell_measurement_theta_min      4.2360
_cell_volume                     2304.98(11)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28903
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         4.248
_exptl_absorpt_coefficient_mu    2.271
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       slab
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4125
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0373
_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)+(0.0590P)²+1.2237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3707
_reflns_number_total             4125
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0305_suppl.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        2304.98(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8104586
_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   0.850
_shelx_estimated_absorpt_t_max   0.945
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.66388(4) 0.62657(2) 0.69139(4) 0.01562(13) Uani 1 1 d . . . . .
C1 C 0.53839(15) 0.56362(8) 0.62594(16) 0.0181(3) Uani 1 1 d . . . . .
H1A H 0.488854 0.570582 0.528740 0.022 Uiso 1 1 calc R U . . .
H1B H 0.578488 0.518304 0.639929 0.022 Uiso 1 1 calc R U . . .
C2 C 0.44665(15) 0.56506(9) 0.68854(16) 0.0181(3) Uani 1 1 d . . . . .
C3 C 0.45914(17) 0.51802(9) 0.78584(18) 0.0220(4) Uani 1 1 d . . . . .
H3 H 0.526472 0.485627 0.813960 0.026 Uiso 1 1 calc R U . . .
C4 C 0.37377(17) 0.51803(9) 0.84239(18) 0.0250(4) Uani 1 1 d . . . . .
H4 H 0.383334 0.485295 0.908223 0.030 Uiso 1 1 calc R U . . .
C5 C 0.27468(16) 0.56510(10) 0.80426(18) 0.0245(4) Uani 1 1 d . . . . .
C6 C 0.26274(17) 0.61190(9) 0.70622(19) 0.0247(4) Uani 1 1 d . . . . .
H6 H 0.195757 0.644485 0.678457 0.030 Uiso 1 1 calc R U . . .
C7 C 0.34649(16) 0.61184(9) 0.64849(18) 0.0221(4) Uani 1 1 d . . . . .
H7 H 0.335655 0.643889 0.581136 0.026 Uiso 1 1 calc R U . . .
C8 C 0.1828(2) 0.56619(12) 0.8659(2) 0.0354(5) Uani 1 1 d . . . . .
H8A H 0.100682 0.546195 0.803840 0.053 Uiso 1 1 calc R U . . .
H8B H 0.168808 0.612995 0.885039 0.053 Uiso 1 1 calc R U . . .
H8C H 0.218968 0.540070 0.948795 0.053 Uiso 1 1 calc R U . . .
C9 C 0.76373(16) 0.61595(9) 0.86637(16) 0.0184(3) Uani 1 1 d . . . . .
C10 C 0.89132(17) 0.59634(10) 0.90970(18) 0.0257(4) Uani 1 1 d . . . . .
H10 H 0.923365 0.587040 0.846684 0.031 Uiso 1 1 calc R U . . .
C11 C 0.97153(18) 0.59042(11) 1.04496(19) 0.0306(4) Uani 1 1 d . . . . .
H11 H 1.058342 0.576716 1.074672 0.037 Uiso 1 1 calc R U . . .
C12 C 0.92509(19) 0.60443(11) 1.13577(18) 0.0292(4) Uani 1 1 d . . . . .
H12 H 0.980914 0.601543 1.228316 0.035 Uiso 1 1 calc R U . . .
C13 C 0.79764(19) 0.62274(10) 1.09400(18) 0.0265(4) Uani 1 1 d . . . . .
H13 H 0.766302 0.631436 1.157797 0.032 Uiso 1 1 calc R U . . .
C14 C 0.71579(17) 0.62837(9) 0.95883(18) 0.0212(4) Uani 1 1 d . . . . .
H14 H 0.628269 0.640524 0.929678 0.025 Uiso 1 1 calc R U . . .
C15 C 0.76258(15) 0.61944(9) 0.60550(16) 0.0202(4) Uani 1 1 d . . . . .
C16 C 0.82950(17) 0.67681(10) 0.59720(19) 0.0269(4) Uani 1 1 d . . . . .
H16 H 0.820107 0.718574 0.633867 0.032 Uiso 1 1 calc R U . . .
C17 C 0.90950(18) 0.67232(12) 0.5352(2) 0.0354(5) Uani 1 1 d . . . . .
H17 H 0.955360 0.710977 0.529450 0.042 Uiso 1 1 calc R U . . .
C18 C 0.92226(19) 0.61126(14) 0.48177(19) 0.0391(6) Uani 1 1 d . . . . .
H18 H 0.976638 0.608362 0.438773 0.047 Uiso 1 1 calc R U . . .
C19 C 0.85674(19) 0.55441(13) 0.4902(2) 0.0392(5) Uani 1 1 d . . . . .
H19 H 0.866171 0.512915 0.452723 0.047 Uiso 1 1 calc R U . . .
C20 C 0.77716(17) 0.55769(11) 0.55335(19) 0.0291(4) Uani 1 1 d . . . . .
H20 H 0.733412 0.518531 0.560840 0.035 Uiso 1 1 calc R U . . .
C21 C 0.59354(15) 0.70929(9) 0.65839(17) 0.0180(3) Uani 1 1 d . . . . .
C22 C 0.62428(17) 0.75873(9) 0.75636(18) 0.0228(4) Uani 1 1 d . . . . .
H22 H 0.685891 0.749612 0.845119 0.027 Uiso 1 1 calc R U . . .
C23 C 0.56456(19) 0.82130(9) 0.72372(19) 0.0277(4) Uani 1 1 d . . . . .
H23 H 0.584550 0.854895 0.790610 0.033 Uiso 1 1 calc R U . . .
C24 C 0.47593(18) 0.83508(9) 0.5941(2) 0.0273(4) Uani 1 1 d . . . . .
H24 H 0.434812 0.877940 0.572573 0.033 Uiso 1 1 calc R U . . .
C25 C 0.44696(17) 0.78643(9) 0.49561(19) 0.0251(4) Uani 1 1 d . . . . .
H25 H 0.387264 0.796395 0.406493 0.030 Uiso 1 1 calc R U . . .
C26 C 0.50479(16) 0.72345(9) 0.52682(17) 0.0213(4) Uani 1 1 d . . . . .
H26 H 0.484478 0.690042 0.459540 0.026 Uiso 1 1 calc R U . . .
Cl1 Cl 0.30604(4) 0.59515(2) 0.28603(4) 0.02762(14) Uani 1 1 d . . . . .
O1W O 0.14804(17) 0.71168(10) 0.35340(19) 0.0513(4) Uani 1 1 d D . . . .
H1W H 0.194(3) 0.6779(11) 0.352(3) 0.062 Uiso 1 1 d D U . . .
H2W H 0.125(3) 0.7319(14) 0.2784(18) 0.062 Uiso 1 1 d D U . . .
O2W O 0.1720(2) 0.77086(9) 0.6001(2) 0.0559(5) Uani 1 1 d D . . . .
H3W H 0.177(3) 0.7648(17) 0.5277(19) 0.067 Uiso 1 1 d D U . . .
H4W H 0.225(2) 0.8002(13) 0.647(3) 0.067 Uiso 1 1 d 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'
Cl Cl 0.3639 0.7018 '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
C21 P1 C9 110.32(8) . .
C21 P1 C15 107.53(8) . .
C9 P1 C15 108.59(8) . .
C21 P1 C1 109.49(8) . .
C9 P1 C1 112.18(8) . .
C15 P1 C1 108.60(8) . .
C2 C1 P1 113.93(11) . .
C2 C1 H1A 108.8 . .
P1 C1 H1A 108.8 . .
C2 C1 H1B 108.8 . .
P1 C1 H1B 108.8 . .
H1A C1 H1B 107.7 . .
C3 C2 C7 118.58(16) . .
C3 C2 C1 120.01(15) . .
C7 C2 C1 121.38(15) . .
C2 C3 C4 120.54(16) . .
C2 C3 H3 119.7 . .
C4 C3 H3 119.7 . .
C5 C4 C3 121.22(17) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C4 C5 C6 117.77(17) . .
C4 C5 C8 121.73(18) . .
C6 C5 C8 120.50(17) . .
C7 C6 C5 121.39(17) . .
C7 C6 H6 119.3 . .
C5 C6 H6 119.3 . .
C6 C7 C2 120.49(17) . .
C6 C7 H7 119.8 . .
C2 C7 H7 119.8 . .
C5 C8 H8A 109.5 . .
C5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C5 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 C14 120.08(16) . .
C10 C9 P1 119.07(13) . .
C14 C9 P1 120.83(13) . .
C11 C10 C9 119.96(17) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C12 C11 C10 119.84(18) . .
C12 C11 H11 120.1 . .
C10 C11 H11 120.1 . .
C11 C12 C13 120.81(17) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C12 C13 C14 120.04(17) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C13 C14 C9 119.23(17) . .
C13 C14 H14 120.4 . .
C9 C14 H14 120.4 . .
C20 C15 C16 120.49(17) . .
C20 C15 P1 121.09(14) . .
C16 C15 P1 118.36(14) . .
C17 C16 C15 119.67(19) . .
C17 C16 H16 120.2 . .
C15 C16 H16 120.2 . .
C18 C17 C16 119.7(2) . .
C18 C17 H17 120.1 . .
C16 C17 H17 120.1 . .
C19 C18 C17 120.79(18) . .
C19 C18 H18 119.6 . .
C17 C18 H18 119.6 . .
C18 C19 C20 120.4(2) . .
C18 C19 H19 119.8 . .
C20 C19 H19 119.8 . .
C19 C20 C15 119.0(2) . .
C19 C20 H20 120.5 . .
C15 C20 H20 120.5 . .
C22 C21 C26 120.01(16) . .
C22 C21 P1 122.95(13) . .
C26 C21 P1 117.03(13) . .
C23 C22 C21 119.69(17) . .
C23 C22 H22 120.2 . .
C21 C22 H22 120.2 . .
C24 C23 C22 120.33(17) . .
C24 C23 H23 119.8 . .
C22 C23 H23 119.8 . .
C23 C24 C25 120.17(17) . .
C23 C24 H24 119.9 . .
C25 C24 H24 119.9 . .
C26 C25 C24 120.21(17) . .
C26 C25 H25 119.9 . .
C24 C25 H25 119.9 . .
C25 C26 C21 119.56(16) . .
C25 C26 H26 120.2 . .
C21 C26 H26 120.2 . .
H1W O1W H2W 105(3) . .
H3W O2W H4W 111(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C21 1.7924(17) .
P1 C9 1.7933(17) .
P1 C15 1.7980(17) .
P1 C1 1.8065(17) .
C1 C2 1.512(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.391(3) .
C2 C7 1.395(2) .
C3 C4 1.392(3) .
C3 H3 0.9500 .
C4 C5 1.392(3) .
C4 H4 0.9500 .
C5 C6 1.395(3) .
C5 C8 1.505(3) .
C6 C7 1.385(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.394(2) .
C9 C14 1.397(2) .
C10 C11 1.388(3) .
C10 H10 0.9500 .
C11 C12 1.374(3) .
C11 H11 0.9500 .
C12 C13 1.388(3) .
C12 H12 0.9500 .
C13 C14 1.390(3) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C20 1.396(3) .
C15 C16 1.401(3) .
C16 C17 1.386(3) .
C16 H16 0.9500 .
C17 C18 1.385(3) .
C17 H17 0.9500 .
C18 C19 1.384(4) .
C18 H18 0.9500 .
C19 C20 1.391(3) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 C22 1.393(3) .
C21 C26 1.402(2) .
C22 C23 1.386(3) .
C22 H22 0.9500 .
C23 C24 1.384(3) .
C23 H23 0.9500 .
C24 C25 1.389(3) .
C24 H24 0.9500 .
C25 C26 1.385(3) .
C25 H25 0.9500 .
C26 H26 0.9500 .
O1W H1W 0.859(10) .
O1W H2W 0.860(10) .
O2W H3W 0.848(10) .
O2W H4W 0.840(10) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C21 P1 C1 C2 -61.83(14) . . . .
C9 P1 C1 C2 60.99(14) . . . .
C15 P1 C1 C2 -178.98(12) . . . .
P1 C1 C2 C3 -101.26(16) . . . .
P1 C1 C2 C7 80.36(18) . . . .
C7 C2 C3 C4 -0.4(3) . . . .
C1 C2 C3 C4 -178.78(15) . . . .
C2 C3 C4 C5 -0.5(3) . . . .
C3 C4 C5 C6 0.7(3) . . . .
C3 C4 C5 C8 -179.23(17) . . . .
C4 C5 C6 C7 -0.1(3) . . . .
C8 C5 C6 C7 179.86(17) . . . .
C5 C6 C7 C2 -0.8(3) . . . .
C3 C2 C7 C6 1.0(3) . . . .
C1 C2 C7 C6 179.38(15) . . . .
C21 P1 C9 C10 -125.31(15) . . . .
C15 P1 C9 C10 -7.71(17) . . . .
C1 P1 C9 C10 112.33(15) . . . .
C21 P1 C9 C14 53.41(16) . . . .
C15 P1 C9 C14 171.01(14) . . . .
C1 P1 C9 C14 -68.95(16) . . . .
C14 C9 C10 C11 -1.3(3) . . . .
P1 C9 C10 C11 177.48(15) . . . .
C9 C10 C11 C12 -0.5(3) . . . .
C10 C11 C12 C13 1.8(3) . . . .
C11 C12 C13 C14 -1.2(3) . . . .
C12 C13 C14 C9 -0.5(3) . . . .
C10 C9 C14 C13 1.8(3) . . . .
P1 C9 C14 C13 -176.95(14) . . . .
C21 P1 C15 C20 -147.05(14) . . . .
C9 P1 C15 C20 93.58(15) . . . .
C1 P1 C15 C20 -28.66(16) . . . .
C21 P1 C15 C16 35.78(15) . . . .
C9 P1 C15 C16 -83.59(15) . . . .
C1 P1 C15 C16 154.17(13) . . . .
C20 C15 C16 C17 0.8(3) . . . .
P1 C15 C16 C17 178.00(14) . . . .
C15 C16 C17 C18 0.2(3) . . . .
C16 C17 C18 C19 -0.4(3) . . . .
C17 C18 C19 C20 -0.3(3) . . . .
C18 C19 C20 C15 1.3(3) . . . .
C16 C15 C20 C19 -1.5(3) . . . .
P1 C15 C20 C19 -178.63(15) . . . .
C9 P1 C21 C22 5.40(17) . . . .
C15 P1 C21 C22 -112.86(15) . . . .
C1 P1 C21 C22 129.32(15) . . . .
C9 P1 C21 C26 -175.17(13) . . . .
C15 P1 C21 C26 66.57(14) . . . .
C1 P1 C21 C26 -51.25(15) . . . .
C26 C21 C22 C23 1.5(3) . . . .
P1 C21 C22 C23 -179.10(14) . . . .
C21 C22 C23 C24 -0.8(3) . . . .
C22 C23 C24 C25 -0.5(3) . . . .
C23 C24 C25 C26 1.2(3) . . . .
C24 C25 C26 C21 -0.5(3) . . . .
C22 C21 C26 C25 -0.8(3) . . . .
P1 C21 C26 C25 179.71(13) . . . .
