#------------------------------------------------------------------------------
#$Date: 2023-05-05 03:29:06 +0300 (Fri, 05 May 2023) $
#$Revision: 283104 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/13/7131327.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_7131327
loop_
_publ_author_name
'Fan, Ya-Xin'
'Huang, Hong-Li'
'Su, Qing-Qiang'
'Lv, Yong-Zheng'
'Li, Shan'
'Ma, Yan-Hua'
'Mao, Yan-Xin'
'Ma, Chun-Lin'
'Du, Ji-Yuan'
_publ_section_title
;
 Brønsted acid-mediated tandem cyclization of triarylphosphines and
 in situ generated ortho-alkynyl quinone methides: access to
 heterocyclic quaternary phosphonium salts.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3463
_journal_page_last               3466
_journal_paper_doi               10.1039/d2cc06994f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_sum            'C34 H26 F3 O4 P S'
_chemical_formula_weight         618.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2022-11-11 deposited with the CCDC.	2023-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                98.275(2)
_cell_angle_beta                 97.020(2)
_cell_angle_gamma                116.223(4)
_cell_formula_units_Z            2
_cell_length_a                   9.7924(8)
_cell_length_b                   10.8723(9)
_cell_length_c                   16.3126(14)
_cell_measurement_reflns_used    1900
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.0985
_cell_measurement_theta_min      2.371
_cell_volume                     1507.6(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0741
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7386
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.142
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   0.979
_exptl_transmission_factor_min   0.947
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0707
_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)+(0.1108P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.1939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3238
_reflns_number_total             5199
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc06994f2.cif
_cod_data_source_block           211113e
_cod_depositor_comments
'Adding full bibliography for 7131326--7131327.cif.'
_cod_database_code               7131327
_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   0.916
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.16617(11) 0.84764(9) 0.26056(6) 0.0337(3) Uani 1 1 d . . . . .
S1 S 0.01266(13) 0.72584(11) 0.72148(7) 0.0500(3) Uani 1 1 d . . . . .
O1 O 0.3567(3) 1.2610(2) 0.26919(16) 0.0450(7) Uani 1 1 d . . . . .
C29 C 0.3613(4) 1.1247(4) 0.3619(2) 0.0338(8) Uani 1 1 d . . . . .
C6 C 0.0624(4) 0.8061(4) 0.3455(2) 0.0351(9) Uani 1 1 d . . . . .
C27 C 0.2623(4) 1.0342(3) 0.2792(2) 0.0331(8) Uani 1 1 d . . . . .
C18 C 0.3103(4) 0.7871(4) 0.2623(2) 0.0354(9) Uani 1 1 d . . . . .
C26 C 0.2640(4) 1.1233(4) 0.2273(2) 0.0389(9) Uani 1 1 d . . . . .
C28 C 0.4168(5) 1.2612(4) 0.3508(2) 0.0395(9) Uani 1 1 d . . . . .
O4 O -0.1005(4) 0.6157(3) 0.6512(2) 0.0727(10) Uani 1 1 d . . . . .
C30 C 0.4103(5) 1.1028(4) 0.4406(2) 0.0442(10) Uani 1 1 d . . . . .
H30 H 0.3749 1.0126 0.4504 0.053 Uiso 1 1 calc R U . . .
C5 C -0.0208(4) 0.8782(4) 0.3660(2) 0.0426(9) Uani 1 1 d . . . . .
H5 H -0.0197 0.9465 0.3374 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4687(4) 0.8821(4) 0.2780(2) 0.0402(9) Uani 1 1 d . . . . .
H11 H 0.5012 0.9783 0.2883 0.048 Uiso 1 1 calc R U . . .
C33 C 0.5204(5) 1.3804(4) 0.4125(3) 0.0497(11) Uani 1 1 d . . . . .
H33 H 0.5555 1.4705 0.4027 0.060 Uiso 1 1 calc R U . . .
C7 C 0.2614(5) 0.6422(4) 0.2461(2) 0.0463(10) Uani 1 1 d . . . . .
H7 H 0.1559 0.5785 0.2341 0.056 Uiso 1 1 calc R U . . .
C25 C 0.1892(5) 1.1049(4) 0.1380(2) 0.0443(10) Uani 1 1 d . . . . .
H25A H 0.1488 1.1717 0.1366 0.053 Uiso 1 1 calc R U . . .
H25B H 0.1012 1.0113 0.1199 0.053 Uiso 1 1 calc R U . . .
F2 F 0.3132(3) 0.8142(3) 0.7677(2) 0.0943(10) Uani 1 1 d . . . . .
C24 C 0.2942(5) 1.1240(4) 0.0749(2) 0.0471(10) Uani 1 1 d . . . . .
C17 C 0.0323(5) 0.7627(4) 0.1590(2) 0.0410(9) Uani 1 1 d . . . . .
O3 O -0.0090(4) 0.6967(3) 0.80317(19) 0.0718(10) Uani 1 1 d . . . . .
C10 C 0.5764(5) 0.8332(4) 0.2781(3) 0.0533(11) Uani 1 1 d . . . . .
H10 H 0.6819 0.8963 0.2879 0.064 Uiso 1 1 calc R U . . .
O2 O 0.0503(4) 0.8669(3) 0.7162(2) 0.0860(11) Uani 1 1 d . . . . .
C1 C 0.0605(5) 0.7038(4) 0.3889(2) 0.0489(11) Uani 1 1 d . . . . .
H1 H 0.1139 0.6538 0.3751 0.059 Uiso 1 1 calc R U . . .
C4 C -0.1051(5) 0.8477(4) 0.4294(3) 0.0546(11) Uani 1 1 d . . . . .
H4 H -0.1611 0.8955 0.4426 0.066 Uiso 1 1 calc R U . . .
C3 C -0.1070(5) 0.7476(5) 0.4732(3) 0.0567(12) Uani 1 1 d . . . . .
H3 H -0.1642 0.7276 0.5154 0.068 Uiso 1 1 calc R U . . .
C32 C 0.5679(5) 1.3561(4) 0.4893(3) 0.0549(12) Uani 1 1 d . . . . .
H32 H 0.6379 1.4322 0.5326 0.066 Uiso 1 1 calc R U . . .
C31 C 0.5135(5) 1.2204(4) 0.5034(2) 0.0514(11) Uani 1 1 d . . . . .
H31 H 0.5469 1.2083 0.5561 0.062 Uiso 1 1 calc R U . . .
C9 C 0.5277(5) 0.6891(5) 0.2634(3) 0.0575(12) Uani 1 1 d . . . . .
H9 H 0.6011 0.6567 0.2641 0.069 Uiso 1 1 calc R U . . .
C8 C 0.3715(5) 0.5943(4) 0.2480(3) 0.0535(11) Uani 1 1 d . . . . .
H8 H 0.3400 0.4984 0.2388 0.064 Uiso 1 1 calc R U . . .
F3 F 0.1812(5) 0.5945(4) 0.7227(3) 0.1459(18) Uani 1 1 d . . . . .
C2 C -0.0234(6) 0.6777(5) 0.4538(3) 0.0639(13) Uani 1 1 d . . . . .
H2 H -0.0225 0.6120 0.4843 0.077 Uiso 1 1 calc R U . . .
C12 C 0.0876(6) 0.7351(5) 0.0876(3) 0.0630(13) Uani 1 1 d . . . . .
H12 H 0.1927 0.7604 0.0922 0.076 Uiso 1 1 calc R U . . .
F1 F 0.2251(5) 0.7365(6) 0.6367(3) 0.157(2) Uani 1 1 d . . . . .
C34 C 0.1912(6) 0.7183(5) 0.7114(4) 0.0720(14) Uani 1 1 d . . . . .
C13 C -0.0147(8) 0.6696(5) 0.0090(3) 0.0772(16) Uani 1 1 d . . . . .
H13 H 0.0223 0.6515 -0.0388 0.093 Uiso 1 1 calc R U . . .
C23 C 0.4487(6) 1.2279(6) 0.0929(3) 0.0744(15) Uani 1 1 d . . . . .
H23 H 0.4922 1.2874 0.1464 0.089 Uiso 1 1 calc R U . . .
C16 C -0.1237(6) 0.7259(6) 0.1508(3) 0.0772(16) Uani 1 1 d . . . . .
H16 H -0.1620 0.7451 0.1978 0.093 Uiso 1 1 calc R U . . .
C19 C 0.2333(7) 1.0379(5) -0.0067(3) 0.0686(14) Uani 1 1 d . . . . .
H19 H 0.1305 0.9673 -0.0206 0.082 Uiso 1 1 calc R U . . .
C14 C -0.1699(8) 0.6317(5) 0.0022(3) 0.0849(18) Uani 1 1 d . . . . .
H14 H -0.2385 0.5866 -0.0500 0.102 Uiso 1 1 calc R U . . .
C22 C 0.5393(7) 1.2440(8) 0.0315(4) 0.111(2) Uani 1 1 d . . . . .
H22 H 0.6428 1.3131 0.0447 0.133 Uiso 1 1 calc R U . . .
C21 C 0.4770(9) 1.1593(9) -0.0475(4) 0.125(3) Uani 1 1 d . . . . .
H21 H 0.5378 1.1710 -0.0882 0.150 Uiso 1 1 calc R U . . .
C15 C -0.2230(7) 0.6603(7) 0.0721(4) 0.102(2) Uani 1 1 d . . . . .
H15 H -0.3281 0.6352 0.0670 0.122 Uiso 1 1 calc R U . . .
C20 C 0.3251(9) 1.0569(8) -0.0672(4) 0.103(2) Uani 1 1 d . . . . .
H20 H 0.2829 0.9996 -0.1214 0.124 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
F F 0.0171 0.0103 '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
C27 P1 C18 108.69(17) . . ?
C27 P1 C6 105.50(16) . . ?
C18 P1 C6 111.84(16) . . ?
C27 P1 C17 113.63(17) . . ?
C18 P1 C17 107.08(17) . . ?
C6 P1 C17 110.19(18) . . ?
O2 S1 O3 114.3(2) . . ?
O2 S1 O4 116.5(2) . . ?
O3 S1 O4 114.3(2) . . ?
O2 S1 C34 102.9(2) . . ?
O3 S1 C34 103.5(2) . . ?
O4 S1 C34 102.9(2) . . ?
C26 O1 C28 107.5(3) . . ?
C28 C29 C30 118.8(3) . . ?
C28 C29 C27 105.3(3) . . ?
C30 C29 C27 135.9(3) . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 P1 117.7(3) . . ?
C1 C6 P1 122.6(3) . . ?
C26 C27 C29 106.2(3) . . ?
C26 C27 P1 131.2(3) . . ?
C29 C27 P1 122.5(2) . . ?
C11 C18 C7 120.0(4) . . ?
C11 C18 P1 121.0(3) . . ?
C7 C18 P1 119.1(3) . . ?
C27 C26 O1 110.7(3) . . ?
C27 C26 C25 135.1(3) . . ?
O1 C26 C25 114.2(3) . . ?
C29 C28 O1 110.2(3) . . ?
C29 C28 C33 124.5(4) . . ?
O1 C28 C33 125.3(3) . . ?
C31 C30 C29 117.8(4) . . ?
C4 C5 C6 119.8(4) . . ?
C10 C11 C18 119.9(4) . . ?
C32 C33 C28 115.7(4) . . ?
C8 C7 C18 119.6(4) . . ?
C26 C25 C24 115.3(3) . . ?
C23 C24 C19 117.6(4) . . ?
C23 C24 C25 123.1(4) . . ?
C19 C24 C25 119.3(4) . . ?
C16 C17 C12 119.2(4) . . ?
C16 C17 P1 121.2(3) . . ?
C12 C17 P1 119.6(3) . . ?
C11 C10 C9 120.1(4) . . ?
C6 C1 C2 118.9(4) . . ?
C3 C4 C5 120.9(4) . . ?
C2 C3 C4 119.4(4) . . ?
C33 C32 C31 121.6(4) . . ?
C30 C31 C32 121.6(4) . . ?
C8 C9 C10 120.6(4) . . ?
C9 C8 C7 119.9(4) . . ?
C3 C2 C1 121.2(4) . . ?
C17 C12 C13 120.0(5) . . ?
F2 C34 F1 106.0(5) . . ?
F2 C34 F3 105.2(4) . . ?
F1 C34 F3 109.0(5) . . ?
F2 C34 S1 113.7(4) . . ?
F1 C34 S1 111.6(4) . . ?
F3 C34 S1 111.0(4) . . ?
C14 C13 C12 120.0(5) . . ?
C24 C23 C22 120.8(5) . . ?
C17 C16 C15 119.6(5) . . ?
C20 C19 C24 120.6(5) . . ?
C15 C14 C13 119.8(5) . . ?
C21 C22 C23 120.4(6) . . ?
C22 C21 C20 120.1(6) . . ?
C14 C15 C16 121.4(6) . . ?
C21 C20 C19 120.4(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 C27 1.777(3) . ?
P1 C18 1.801(4) . ?
P1 C6 1.809(4) . ?
P1 C17 1.810(4) . ?
S1 O2 1.429(3) . ?
S1 O3 1.432(3) . ?
S1 O4 1.448(3) . ?
S1 C34 1.811(6) . ?
O1 C26 1.374(4) . ?
O1 C28 1.388(4) . ?
C29 C28 1.385(5) . ?
C29 C30 1.405(5) . ?
C29 C27 1.478(5) . ?
C6 C5 1.395(5) . ?
C6 C1 1.397(5) . ?
C27 C26 1.371(5) . ?
C18 C11 1.396(5) . ?
C18 C7 1.401(5) . ?
C26 C25 1.492(5) . ?
C28 C33 1.390(5) . ?
C30 C31 1.390(5) . ?
C5 C4 1.388(5) . ?
C11 C10 1.376(6) . ?
C33 C32 1.386(6) . ?
C7 C8 1.389(6) . ?
C25 C24 1.514(5) . ?
F2 C34 1.309(5) . ?
C24 C23 1.392(6) . ?
C24 C19 1.399(6) . ?
C17 C16 1.381(6) . ?
C17 C12 1.392(6) . ?
C10 C9 1.393(6) . ?
C1 C2 1.403(6) . ?
C4 C3 1.380(6) . ?
C3 C2 1.375(6) . ?
C32 C31 1.395(6) . ?
C9 C8 1.380(6) . ?
F3 C34 1.347(6) . ?
C12 C13 1.395(6) . ?
F1 C34 1.321(6) . ?
C13 C14 1.373(8) . ?
C23 C22 1.396(7) . ?
C16 C15 1.386(7) . ?
C19 C20 1.392(8) . ?
C14 C15 1.362(8) . ?
C22 C21 1.360(8) . ?
C21 C20 1.369(9) . ?
