#------------------------------------------------------------------------------
#$Date: 2018-09-27 07:13:35 +0300 (Thu, 27 Sep 2018) $
#$Revision: 211196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/94/2229497.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229497
loop_
_publ_author_name
'Ceylan, Ümit'
'Tanak, Hasan'
'Türkkan, Ercan'
'Dereli, Ömer'
'Büyükgüngör, Orhan'
_publ_section_title
;
 (2-Hydroxyethyl)triphenylphosphonium chloride
;
_journal_coeditor_code           RZ2551
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o641
_journal_paper_doi               10.1107/S160053681100482X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H20 O P +, Cl -'
_chemical_formula_moiety         'C20 H20 O P +, Cl -'
_chemical_formula_sum            'C20 H20 Cl O P'
_chemical_formula_weight         342.78
_chemical_name_systematic
;
(2-Hydroxyethyl)triphenylphosphonium chloride
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.510(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.1988(4)
_cell_length_b                   12.5743(3)
_cell_length_c                   19.7098(6)
_cell_measurement_reflns_used    36925
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.28
_cell_measurement_theta_min      2.07
_cell_volume                     3515.61(17)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26668
_diffrn_reflns_theta_full        26.77
_diffrn_reflns_theta_max         26.77
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.9046
_exptl_absorpt_correction_T_min  0.5989
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.707
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.235
_refine_ls_extinction_coef       0.0106(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3725
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0495P)²+1.6584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                3317
_reflns_number_total             3725
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2551.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2229497
_cod_database_fobs_code          2229497
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.25807(3) 0.74387(4) 0.18184(2) 0.06015(16) Uani d . 1 . .
P P1 0.22348(3) 0.60936(3) 0.37482(2) 0.04301(14) Uani d . 1 A .
C C1 0.34518(11) 0.64165(12) 0.39231(8) 0.0449(3) Uani d . 1 . .
C C2 0.39771(12) 0.68183(14) 0.33985(9) 0.0545(4) Uani d . 1 . .
H H2 0.3690 0.6949 0.2973 0.065 Uiso calc R 1 . .
C C3 0.49228(13) 0.70205(16) 0.35142(11) 0.0633(5) Uani d . 1 . .
H H3 0.5273 0.7292 0.3166 0.076 Uiso calc R 1 . .
C C4 0.53530(13) 0.68242(17) 0.41386(11) 0.0655(5) Uani d . 1 . .
H H4 0.5994 0.6958 0.4210 0.079 Uiso calc R 1 . .
C C5 0.48442(14) 0.64332(17) 0.46574(10) 0.0652(5) Uani d . 1 . .
H H5 0.5140 0.6305 0.5080 0.078 Uiso calc R 1 . .
C C6 0.38882(12) 0.62269(15) 0.45550(9) 0.0543(4) Uani d . 1 . .
H H6 0.3542 0.5963 0.4908 0.065 Uiso calc R 1 . .
C C7 0.18175(11) 0.54012(13) 0.44737(8) 0.0457(3) Uani d . 1 . .
C C8 0.21070(14) 0.43627(15) 0.46028(9) 0.0606(5) Uani d . 1 . .
H H8 0.2449 0.3994 0.4287 0.073 Uiso calc R 1 . .
C C9 0.18823(16) 0.38821(15) 0.52053(10) 0.0665(5) Uani d . 1 . .
H H9 0.2087 0.3193 0.5298 0.080 Uiso calc R 1 . .
C C10 0.13605(13) 0.44101(16) 0.56677(9) 0.0608(5) Uani d . 1 . .
H H10 0.1221 0.4082 0.6074 0.073 Uiso calc R 1 . .
C C11 0.10449(13) 0.54206(17) 0.55326(9) 0.0617(5) Uani d . 1 . .
H H11 0.0675 0.5769 0.5841 0.074 Uiso calc R 1 . .
C C12 0.12762(12) 0.59252(14) 0.49368(9) 0.0527(4) Uani d . 1 . .
H H12 0.1068 0.6615 0.4848 0.063 Uiso calc R 1 . .
C C13 0.15396(11) 0.72717(13) 0.36117(8) 0.0450(3) Uani d . 1 . .
C C14 0.05633(12) 0.71654(16) 0.34952(10) 0.0581(4) Uani d . 1 . .
H H14 0.0288 0.6494 0.3490 0.070 Uiso calc R 1 . .
C C15 0.00133(13) 0.80521(18) 0.33882(10) 0.0667(5) Uani d . 1 . .
H H15 -0.0634 0.7980 0.3308 0.080 Uiso calc R 1 . .
C C16 0.04150(15) 0.90428(17) 0.33992(10) 0.0677(5) Uani d . 1 . .
H H16 0.0037 0.9640 0.3329 0.081 Uiso calc R 1 . .
C C17 0.13779(15) 0.91629(15) 0.35143(10) 0.0629(5) Uani d . 1 . .
H H17 0.1646 0.9838 0.3522 0.076 Uiso calc R 1 . .
C C18 0.19394(12) 0.82728(13) 0.36184(9) 0.0510(4) Uani d . 1 . .
H H18 0.2587 0.8349 0.3693 0.061 Uiso calc R 1 . .
C C19 0.22152(13) 0.52738(14) 0.29984(8) 0.0548(4) Uani d D 1 . .
H H19A 0.2554 0.5656 0.2658 0.066 Uiso calc PR 0.554(4) A 1
H H19B 0.2580 0.4641 0.3111 0.066 Uiso calc PR 0.554(4) A 1
H H19C 0.2453 0.5679 0.2624 0.066 Uiso calc PR 0.446(4) A 2
H H19D 0.2628 0.4668 0.3078 0.066 Uiso calc PR 0.446(4) A 2
O O1A 0.0805(2) 0.4345(3) 0.31380(16) 0.0879(10) Uani d PDU 0.554(4) A 1
H H1A 0.1117 0.3827 0.3265 0.132 Uiso calc PR 0.554(4) A 1
C C20A 0.1293(4) 0.4906(5) 0.2660(4) 0.0667(14) Uani d PDU 0.554(4) A 1
H H20A 0.0926 0.5514 0.2500 0.080 Uiso calc PR 0.554(4) A 1
H H20B 0.1414 0.4454 0.2275 0.080 Uiso calc PR 0.554(4) A 1
O O1B 0.1262(3) 0.4096(3) 0.23172(16) 0.0766(11) Uani d PDU 0.446(4) A 2
H H1B 0.1513 0.3564 0.2483 0.115 Uiso calc PR 0.446(4) A 2
C C20B 0.1230(4) 0.4883(6) 0.2807(6) 0.0672(17) Uani d PDU 0.446(4) A 2
H H20C 0.0940 0.4603 0.3206 0.081 Uiso calc PR 0.446(4) A 2
H H20D 0.0848 0.5471 0.2634 0.081 Uiso calc PR 0.446(4) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 P1 C13 . . 111.16(7) ?
C1 P1 C7 . . 107.77(7) ?
C13 P1 C7 . . 108.73(7) ?
C1 P1 C19 . . 105.51(8) ?
C13 P1 C19 . . 111.16(8) ?
C7 P1 C19 . . 112.45(8) ?
C6 C1 C2 . . 119.68(15) ?
C6 C1 P1 . . 121.49(12) ?
C2 C1 P1 . . 118.76(12) ?
C3 C2 C1 . . 119.56(17) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C4 C3 C2 . . 120.56(18) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C5 C4 C3 . . 120.38(18) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.22(18) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 119.60(17) ?
C1 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
C12 C7 C8 . . 119.65(15) ?
C12 C7 P1 . . 120.38(13) ?
C8 C7 P1 . . 119.74(12) ?
C9 C8 C7 . . 119.39(17) ?
C9 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C10 C9 C8 . . 120.75(18) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C11 C10 C9 . . 120.12(16) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C12 . . 120.10(17) ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C7 C12 C11 . . 119.94(17) ?
C7 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C18 C13 C14 . . 119.46(16) ?
C18 C13 P1 . . 121.88(12) ?
C14 C13 P1 . . 118.66(13) ?
C15 C14 C13 . . 120.00(18) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C16 C15 C14 . . 120.17(18) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C17 . . 120.62(18) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C18 C17 C16 . . 119.63(18) ?
C18 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C13 C18 C17 . . 120.12(16) ?
C13 C18 H18 . . 119.9 ?
C17 C18 H18 . . 119.9 ?
C20A C19 P1 . . 121.2(4) ?
C20B C19 P1 . . 111.8(4) ?
C20A C19 H19A . . 107.0 ?
C20B C19 H19A . . 118.0 ?
P1 C19 H19A . . 107.0 ?
C20A C19 H19B . . 107.0 ?
C20B C19 H19B . . 105.6 ?
P1 C19 H19B . . 107.0 ?
H19A C19 H19B . . 106.8 ?
C20A C19 H19C . . 98.6 ?
C20B C19 H19C . . 109.3 ?
P1 C19 H19C . . 109.3 ?
H19B C19 H19C . . 113.9 ?
C20A C19 H19D . . 109.6 ?
C20B C19 H19D . . 109.3 ?
P1 C19 H19D . . 109.3 ?
H19A C19 H19D . . 100.8 ?
H19C C19 H19D . . 107.9 ?
O1A C20A C19 . . 107.7(5) ?
O1A C20A H20A . . 110.2 ?
C19 C20A H20A . . 110.2 ?
O1A C20A H20B . . 110.2 ?
C19 C20A H20B . . 110.2 ?
H20A C20A H20B . . 108.5 ?
C20B O1B H1B . . 109.5 ?
O1B C20B C19 . . 110.3(6) ?
O1B C20B H20C . . 109.6 ?
C19 C20B H20C . . 109.6 ?
O1B C20B H20D . . 109.6 ?
C19 C20B H20D . . 109.6 ?
H20C C20B H20D . . 108.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C1 . 1.7938(16) ?
P1 C13 . 1.7939(16) ?
P1 C7 . 1.7968(15) ?
P1 C19 . 1.8009(17) ?
C1 C6 . 1.387(2) ?
C1 C2 . 1.396(2) ?
C2 C3 . 1.376(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.372(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.385(2) ?
C7 C8 . 1.389(2) ?
C8 C9 . 1.382(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.371(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.370(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.387(2) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C18 . 1.381(2) ?
C13 C14 . 1.401(2) ?
C14 C15 . 1.372(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.370(3) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.384(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.384(2) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 C20A . 1.515(4) ?
C19 C20B . 1.516(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C19 H19C . 0.9700 ?
C19 H19D . 0.9700 ?
O1A C20A . 1.386(8) ?
O1A H1A . 0.8200 ?
C20A H20A . 0.9700 ?
C20A H20B . 0.9700 ?
O1B C20B . 1.383(8) ?
O1B H1B . 0.8200 ?
C20B H20C . 0.9700 ?
C20B H20D . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 Cl1 . 0.93 2.78 3.7009(19) 171
C19 H19C Cl1 . 0.97 2.73 3.6325(18) 154
O1B H1B Cl1 4_545 0.82 2.32 3.115(4) 162
O1A H1A Cl1 4_545 0.82 2.55 3.314(4) 155
C19 H19B Cl1 4_545 0.97 2.78 3.5935(19) 142
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 P1 C1 C6 . . . . 112.88(14) ?
C7 P1 C1 C6 . . . . -6.17(16) ?
C19 P1 C1 C6 . . . . -126.51(14) ?
C13 P1 C1 C2 . . . . -70.32(15) ?
C7 P1 C1 C2 . . . . 170.63(13) ?
C19 P1 C1 C2 . . . . 50.29(15) ?
C6 C1 C2 C3 . . . . 0.1(3) ?
P1 C1 C2 C3 . . . . -176.77(14) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C2 C3 C4 C5 . . . . -0.6(3) ?
C3 C4 C5 C6 . . . . 0.3(3) ?
C2 C1 C6 C5 . . . . -0.4(3) ?
P1 C1 C6 C5 . . . . 176.39(14) ?
C4 C5 C6 C1 . . . . 0.2(3) ?
C1 P1 C7 C12 . . . . 101.87(14) ?
C13 P1 C7 C12 . . . . -18.72(16) ?
C19 P1 C7 C12 . . . . -142.27(14) ?
C1 P1 C7 C8 . . . . -72.50(16) ?
C13 P1 C7 C8 . . . . 166.91(14) ?
C19 P1 C7 C8 . . . . 43.36(17) ?
C12 C7 C8 C9 . . . . -2.6(3) ?
P1 C7 C8 C9 . . . . 171.81(16) ?
C7 C8 C9 C10 . . . . 1.5(3) ?
C8 C9 C10 C11 . . . . 0.8(3) ?
C9 C10 C11 C12 . . . . -2.0(3) ?
C8 C7 C12 C11 . . . . 1.5(3) ?
P1 C7 C12 C11 . . . . -172.90(14) ?
C10 C11 C12 C7 . . . . 0.8(3) ?
C1 P1 C13 C18 . . . . 2.53(16) ?
C7 P1 C13 C18 . . . . 121.01(14) ?
C19 P1 C13 C18 . . . . -114.68(15) ?
C1 P1 C13 C14 . . . . -177.47(13) ?
C7 P1 C13 C14 . . . . -58.99(15) ?
C19 P1 C13 C14 . . . . 65.32(15) ?
C18 C13 C14 C15 . . . . 0.1(3) ?
P1 C13 C14 C15 . . . . -179.91(15) ?
C13 C14 C15 C16 . . . . -0.4(3) ?
C14 C15 C16 C17 . . . . 0.3(3) ?
C15 C16 C17 C18 . . . . 0.1(3) ?
C14 C13 C18 C17 . . . . 0.3(2) ?
P1 C13 C18 C17 . . . . -179.67(13) ?
C16 C17 C18 C13 . . . . -0.4(3) ?
C1 P1 C19 C20A . . . . -175.4(3) ?
C13 P1 C19 C20A . . . . -54.8(3) ?
C7 P1 C19 C20A . . . . 67.4(3) ?
C1 P1 C19 C20B . . . . 176.9(4) ?
C13 P1 C19 C20B . . . . -62.5(4) ?
C7 P1 C19 C20B . . . . 59.6(4) ?
C20B C19 C20A O1A . . . . -20(2) ?
P1 C19 C20A O1A . . . . -57.9(5) ?
C20A C19 C20B O1B . . . . 47(2) ?
P1 C19 C20B O1B . . . . -168.2(5) ?
