#------------------------------------------------------------------------------
#$Date: 2025-11-29 18:49:30 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303556 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/50/7135096.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_7135096
loop_
_publ_author_name
'Kopp, Richard O.'
'Rigo, Massimo'
'Groth, Lucie J.'
'Coles, Nathan T.'
'Neale, Samuel E.'
'Frank, Samantha'
'Ernst, Moritz J.'
'Weber, Manuela'
'Müller, Christian'
_publ_section_title
;
 Dynamic activation of alcohols by an electrophilic phosphinine.
;
_journal_issue                   94
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              18625
_journal_page_last               18628
_journal_paper_doi               10.1039/d5cc05302a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C17 H19 F6 O P Si'
_chemical_formula_sum            'C17 H19 F6 O P Si'
_chemical_formula_weight         412.38
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-09-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-09-11 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                99.1849(11)
_cell_angle_beta                 91.1844(10)
_cell_angle_gamma                112.8005(9)
_cell_formula_units_Z            2
_cell_length_a                   8.9992(2)
_cell_length_b                   10.1647(3)
_cell_length_c                   11.3907(3)
_cell_measurement_reflns_used    7640
_cell_measurement_temperature    100.03
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.58
_cell_volume                     944.31(4)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.03
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14905
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.430
_diffrn_reflns_theta_min         2.465
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_correction_T_min  0.9285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1218 before and 0.0478 after correction.
The Ratio of minimum to maximum transmission is 0.9690.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0391
_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)+(0.0315P)²+0.7493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3092
_reflns_number_total             3879
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc05302a2.cif
_cod_data_source_block           mr336_mw
_cod_depositor_comments
'Adding full bibliography for 7135096--7135097.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7135096
_shelx_shelxl_version_number     2018/3
_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_max   0.976
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.67147(6) 0.38797(5) 0.54623(4) 0.01392(13) Uani 1 1 d . . . . .
H1 H 0.707(2) 0.525(2) 0.5597(17) 0.016(5) Uiso 1 1 d . . . . .
Si1 Si 0.62049(7) 0.40253(6) 0.81491(5) 0.01413(13) Uani 1 1 d . . . . .
F1 F 0.91984(16) 0.03451(13) 0.38832(11) 0.0277(3) Uani 1 1 d . . . . .
F2 F 1.06585(15) 0.24550(14) 0.35502(11) 0.0302(3) Uani 1 1 d . . . . .
F3 F 0.83099(16) 0.12316(14) 0.25835(10) 0.0291(3) Uani 1 1 d . . . . .
F4 F 0.93287(16) 0.41730(15) 0.28091(11) 0.0317(3) Uani 1 1 d . . . . .
F5 F 0.67625(15) 0.30168(14) 0.23915(10) 0.0281(3) Uani 1 1 d . . . . .
F6 F 0.77005(17) 0.51617(14) 0.34501(11) 0.0315(3) Uani 1 1 d . . . . .
O1 O 0.48401(17) 0.33912(14) 0.50348(12) 0.0180(3) Uani 1 1 d . . . . .
C1 C 0.6979(2) 0.3287(2) 0.67640(16) 0.0133(4) Uani 1 1 d . . . . .
C2 C 0.7672(2) 0.2276(2) 0.67048(16) 0.0127(4) Uani 1 1 d . . . . .
C3 C 0.8312(2) 0.1778(2) 0.56875(17) 0.0154(4) Uani 1 1 d . . . . .
H3 H 0.873438 0.106501 0.574590 0.018 Uiso 1 1 calc R U . . .
C4 C 0.8367(2) 0.2255(2) 0.46185(17) 0.0149(4) Uani 1 1 d . . . . .
C5 C 0.7793(2) 0.3315(2) 0.44029(17) 0.0154(4) Uani 1 1 d . . . . .
C11 C 0.3831(3) 0.1854(2) 0.4750(2) 0.0238(5) Uani 1 1 d . . . . .
H11A H 0.382795 0.149971 0.389692 0.036 Uiso 1 1 calc R U . . .
H11B H 0.272320 0.169241 0.493894 0.036 Uiso 1 1 calc R U . . .
H11C H 0.425843 0.132975 0.521972 0.036 Uiso 1 1 calc R U . . .
C21 C 0.6269(3) 0.5849(2) 0.79935(19) 0.0223(5) Uani 1 1 d . . . . .
H21A H 0.581164 0.622397 0.867634 0.033 Uiso 1 1 calc R U . . .
H21B H 0.563647 0.576244 0.725349 0.033 Uiso 1 1 calc R U . . .
H21C H 0.739401 0.651644 0.796903 0.033 Uiso 1 1 calc R U . . .
C22 C 0.7477(3) 0.4271(2) 0.95442(18) 0.0234(5) Uani 1 1 d . . . . .
H22A H 0.717034 0.483402 1.020296 0.035 Uiso 1 1 calc R U . . .
H22B H 0.861974 0.478871 0.942934 0.035 Uiso 1 1 calc R U . . .
H22C H 0.730824 0.331886 0.973379 0.035 Uiso 1 1 calc R U . . .
C23 C 0.4060(3) 0.2797(2) 0.8252(2) 0.0240(5) Uani 1 1 d . . . . .
H23A H 0.399983 0.182179 0.829327 0.036 Uiso 1 1 calc R U . . .
H23B H 0.338995 0.275227 0.754566 0.036 Uiso 1 1 calc R U . . .
H23C H 0.366446 0.317107 0.897145 0.036 Uiso 1 1 calc R U . . .
C31 C 0.7790(2) 0.1618(2) 0.77673(17) 0.0148(4) Uani 1 1 d . . . . .
C32 C 0.6433(3) 0.0550(2) 0.80987(17) 0.0179(4) Uani 1 1 d . . . . .
H32 H 0.541369 0.025201 0.765782 0.022 Uiso 1 1 calc R U . . .
C33 C 0.6558(3) -0.0082(2) 0.90693(19) 0.0245(5) Uani 1 1 d . . . . .
H33 H 0.563135 -0.082429 0.928239 0.029 Uiso 1 1 calc R U . . .
C34 C 0.8036(3) 0.0370(3) 0.97256(19) 0.0289(6) Uani 1 1 d . . . . .
H34 H 0.811825 -0.004712 1.040056 0.035 Uiso 1 1 calc R U . . .
C35 C 0.9391(3) 0.1426(3) 0.9402(2) 0.0286(5) Uani 1 1 d . . . . .
H35 H 1.040244 0.173559 0.985698 0.034 Uiso 1 1 calc R U . . .
C36 C 0.9281(3) 0.2038(2) 0.84154(18) 0.0215(5) Uani 1 1 d . . . . .
H36 H 1.022309 0.274290 0.818145 0.026 Uiso 1 1 calc R U . . .
C41 C 0.9125(3) 0.1578(2) 0.36589(18) 0.0203(5) Uani 1 1 d . . . . .
C51 C 0.7910(3) 0.3896(2) 0.32770(18) 0.0211(5) Uani 1 1 d . . . . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 H1 95.9(9) . . ?
O1 P1 C1 112.18(9) . . ?
O1 P1 C5 113.97(8) . . ?
C1 P1 H1 114.2(9) . . ?
C5 P1 H1 112.1(9) . . ?
C5 P1 C1 108.24(9) . . ?
C21 Si1 C1 108.11(9) . . ?
C22 Si1 C1 112.65(9) . . ?
C22 Si1 C21 107.39(10) . . ?
C22 Si1 C23 110.54(11) . . ?
C23 Si1 C1 109.47(9) . . ?
C23 Si1 C21 108.56(10) . . ?
C11 O1 P1 118.35(12) . . ?
P1 C1 Si1 116.67(11) . . ?
C2 C1 P1 117.93(15) . . ?
C2 C1 Si1 125.33(14) . . ?
C1 C2 C3 125.14(18) . . ?
C1 C2 C31 120.49(17) . . ?
C3 C2 C31 114.37(17) . . ?
C2 C3 H3 117.7 . . ?
C4 C3 C2 124.56(18) . . ?
C4 C3 H3 117.7 . . ?
C3 C4 C5 124.02(18) . . ?
C3 C4 C41 115.15(18) . . ?
C5 C4 C41 120.82(17) . . ?
C4 C5 P1 118.52(14) . . ?
C4 C5 C51 124.94(18) . . ?
C51 C5 P1 116.30(15) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Si1 C21 H21A 109.5 . . ?
Si1 C21 H21B 109.5 . . ?
Si1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Si1 C22 H22A 109.5 . . ?
Si1 C22 H22B 109.5 . . ?
Si1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Si1 C23 H23A 109.5 . . ?
Si1 C23 H23B 109.5 . . ?
Si1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C32 C31 C2 120.71(18) . . ?
C32 C31 C36 119.23(19) . . ?
C36 C31 C2 120.02(18) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.5(2) . . ?
C33 C32 H32 119.8 . . ?
C32 C33 H33 120.1 . . ?
C34 C33 C32 119.8(2) . . ?
C34 C33 H33 120.1 . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.2(2) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 119.9 . . ?
C34 C35 C36 120.3(2) . . ?
C36 C35 H35 119.9 . . ?
C31 C36 H36 120.0 . . ?
C35 C36 C31 120.0(2) . . ?
C35 C36 H36 120.0 . . ?
F1 C41 C4 112.71(16) . . ?
F2 C41 F1 105.39(17) . . ?
F2 C41 C4 112.28(17) . . ?
F3 C41 F1 105.92(16) . . ?
F3 C41 F2 107.24(16) . . ?
F3 C41 C4 112.76(17) . . ?
F4 C51 F5 105.78(16) . . ?
F4 C51 F6 106.21(17) . . ?
F4 C51 C5 114.51(18) . . ?
F5 C51 F6 104.77(17) . . ?
F5 C51 C5 113.93(17) . . ?
F6 C51 C5 110.87(17) . . ?
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 H1 1.28(2) . ?
P1 O1 1.6029(15) . ?
P1 C1 1.7319(19) . ?
P1 C5 1.728(2) . ?
Si1 C1 1.900(2) . ?
Si1 C21 1.869(2) . ?
Si1 C22 1.864(2) . ?
Si1 C23 1.867(2) . ?
F1 C41 1.344(2) . ?
F2 C41 1.343(2) . ?
F3 C41 1.337(2) . ?
F4 C51 1.338(2) . ?
F5 C51 1.355(2) . ?
F6 C51 1.356(2) . ?
O1 C11 1.448(2) . ?
C1 C2 1.388(3) . ?
C2 C3 1.413(3) . ?
C2 C31 1.494(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(3) . ?
C4 C5 1.413(3) . ?
C4 C41 1.513(3) . ?
C5 C51 1.485(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C31 C32 1.391(3) . ?
C31 C36 1.394(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.388(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.383(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.380(4) . ?
C35 H35 0.9500 . ?
C35 C36 1.388(3) . ?
C36 H36 0.9500 . ?
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
_geom_torsion_publ_flag
P1 C1 C2 C3 5.8(3) . . . . ?
P1 C1 C2 C31 -174.20(14) . . . . ?
P1 C5 C51 F4 143.75(15) . . . . ?
P1 C5 C51 F5 -94.28(19) . . . . ?
P1 C5 C51 F6 23.6(2) . . . . ?
Si1 C1 C2 C3 -177.00(15) . . . . ?
Si1 C1 C2 C31 3.0(3) . . . . ?
O1 P1 C1 Si1 -63.14(12) . . . . ?
O1 P1 C1 C2 114.27(15) . . . . ?
O1 P1 C5 C4 -111.67(15) . . . . ?
O1 P1 C5 C51 62.90(17) . . . . ?
C1 P1 O1 C11 -60.95(16) . . . . ?
C1 P1 C5 C4 13.88(18) . . . . ?
C1 P1 C5 C51 -171.55(15) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C2 C31 C32 75.8(2) . . . . ?
C1 C2 C31 C36 -106.4(2) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C3 C4 C41 179.35(18) . . . . ?
C2 C31 C32 C33 178.41(18) . . . . ?
C2 C31 C36 C35 -179.98(18) . . . . ?
C3 C2 C31 C32 -104.3(2) . . . . ?
C3 C2 C31 C36 73.6(2) . . . . ?
C3 C4 C5 P1 -9.0(3) . . . . ?
C3 C4 C5 C51 176.92(19) . . . . ?
C3 C4 C41 F1 17.9(2) . . . . ?
C3 C4 C41 F2 -101.0(2) . . . . ?
C3 C4 C41 F3 137.75(18) . . . . ?
C4 C5 C51 F4 -42.1(3) . . . . ?
C4 C5 C51 F5 79.9(3) . . . . ?
C4 C5 C51 F6 -162.22(18) . . . . ?
C5 P1 O1 C11 62.49(16) . . . . ?
C5 P1 C1 Si1 170.27(10) . . . . ?
C5 P1 C1 C2 -12.33(18) . . . . ?
C5 C4 C41 F1 -163.07(17) . . . . ?
C5 C4 C41 F2 78.1(2) . . . . ?
C5 C4 C41 F3 -43.2(3) . . . . ?
C31 C2 C3 C4 -178.53(18) . . . . ?
C31 C32 C33 C34 1.2(3) . . . . ?
C32 C31 C36 C35 -2.1(3) . . . . ?
C32 C33 C34 C35 -1.4(3) . . . . ?
C33 C34 C35 C36 -0.2(3) . . . . ?
C34 C35 C36 C31 1.9(3) . . . . ?
C36 C31 C32 C33 0.5(3) . . . . ?
C41 C4 C5 P1 172.01(14) . . . . ?
C41 C4 C5 C51 -2.0(3) . . . . ?
