#------------------------------------------------------------------------------
#$Date: 2024-10-04 11:49:52 +0200 (Fri 04 de Oct de 2024) $
#$Revision: 295044 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/27/1572779.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_1572779
loop_
_publ_author_name
'Nguyen, Thi Hong Van'
'Chelli, Saloua'
'Mallet-Ladeira, Sonia'
'Breugst, Martin'
'Lakhdar, Sami'
_publ_section_title
;
 Reactivity of the phosphaethynolate anion with stabilized carbocations:
 mechanistic studies and synthetic applications.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              14406
_journal_page_last               14414
_journal_paper_doi               10.1039/d4sc03518f
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C19 H27 N2 O P, C H2 Cl2'
_chemical_formula_sum            'C20 H29 Cl2 N2 O P'
_chemical_formula_weight         415.32
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-02-09 deposited with the CCDC.	2024-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                61.101(2)
_cell_angle_beta                 89.292(3)
_cell_angle_gamma                66.734(2)
_cell_formula_units_Z            2
_cell_length_a                   10.8087(8)
_cell_length_b                   11.2182(8)
_cell_length_c                   11.3752(8)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.60
_cell_volume                     1081.66(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  triumph
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22682
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.456
_diffrn_reflns_theta_min         3.285
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS(Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         5322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0626P)²+1.8005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1698
_refine_ls_wR_factor_ref         0.1743
_reflns_Friedel_coverage         0
_reflns_number_gt                4583
_reflns_number_total             5322
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03518f74.cif
_cod_data_source_block           10a
_cod_database_code               1572779
_shelx_shelxl_version_number     2019/3
loop_
_symmetry_equiv_pos_as_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
C1 C 0.4005(2) 0.5454(3) 0.7324(2) 0.0201(4) Uani 1 1 d . . . . .
C2 C 0.6173(2) 0.3684(3) 0.7909(2) 0.0235(5) Uani 1 1 d . . . . .
C3 C 0.6209(2) 0.4841(3) 0.7988(2) 0.0242(5) Uani 1 1 d . . . . .
C4 C 0.4208(3) 0.3210(3) 0.7238(3) 0.0243(5) Uani 1 1 d . . . . .
H4 H 0.317997 0.379474 0.701783 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4582(3) 0.1663(3) 0.8512(3) 0.0356(6) Uani 1 1 d . . . . .
H5A H 0.555825 0.098848 0.867183 0.053 Uiso 1 1 calc R U . . .
H5B H 0.400933 0.122678 0.83759 0.053 Uiso 1 1 calc R U . . .
H5C H 0.441874 0.17746 0.93103 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4590(3) 0.3148(4) 0.5969(3) 0.0348(6) Uani 1 1 d . . . . .
H6A H 0.422239 0.418359 0.516644 0.052 Uiso 1 1 calc R U . . .
H6B H 0.419526 0.257385 0.581104 0.052 Uiso 1 1 calc R U . . .
H6C H 0.55972 0.264741 0.611414 0.052 Uiso 1 1 calc R U . . .
C7 C 0.7356(3) 0.2210(3) 0.8263(3) 0.0340(6) Uani 1 1 d . . . . .
H7A H 0.822568 0.227785 0.833645 0.051 Uiso 1 1 calc R U . . .
H7B H 0.726866 0.199065 0.754086 0.051 Uiso 1 1 calc R U . . .
H7C H 0.735082 0.139382 0.914472 0.051 Uiso 1 1 calc R U . . .
C8 C 0.7437(3) 0.4949(4) 0.8422(3) 0.0369(6) Uani 1 1 d . . . . .
H8A H 0.752124 0.468722 0.938283 0.055 Uiso 1 1 calc R U . . .
H8B H 0.732736 0.598907 0.783408 0.055 Uiso 1 1 calc R U . . .
H8C H 0.827103 0.424262 0.833394 0.055 Uiso 1 1 calc R U . . .
C9 C 0.4316(3) 0.7438(3) 0.7504(3) 0.0250(5) Uani 1 1 d . . . . .
H9 H 0.328838 0.784513 0.73587 0.03 Uiso 1 1 calc R U . . .
C10 C 0.4823(3) 0.7302(4) 0.8824(3) 0.0367(6) Uani 1 1 d . . . . .
H10A H 0.473808 0.645633 0.961622 0.055 Uiso 1 1 calc R U . . .
H10B H 0.426414 0.824864 0.880202 0.055 Uiso 1 1 calc R U . . .
H10C H 0.579233 0.711403 0.89058 0.055 Uiso 1 1 calc R U . . .
C11 C 0.4614(4) 0.8556(3) 0.6237(3) 0.0389(7) Uani 1 1 d . . . . .
H11A H 0.561532 0.819511 0.633308 0.058 Uiso 1 1 calc R U . . .
H11B H 0.420165 0.955548 0.614606 0.058 Uiso 1 1 calc R U . . .
H11C H 0.421836 0.863859 0.541518 0.058 Uiso 1 1 calc R U . . .
C12 C 0.2438(2) 0.6318(3) 0.6929(2) 0.0214(4) Uani 1 1 d . . . . .
C13 C -0.0099(3) 0.8112(3) 0.5101(3) 0.0289(5) Uani 1 1 d . . . . .
H13 H -0.01667 0.839749 0.58152 0.035 Uiso 1 1 calc R U . . .
C14 C -0.0823(3) 0.7127(3) 0.5430(3) 0.0363(6) Uani 1 1 d . . . . .
H14 H -0.106752 0.677566 0.629915 0.044 Uiso 1 1 calc R U . . .
C15 C -0.1161(3) 0.6693(4) 0.4624(4) 0.0409(7) Uani 1 1 d . . . . .
H15 H -0.154539 0.599316 0.501123 0.049 Uiso 1 1 calc R U . . .
C16 C -0.1001(3) 0.7176(4) 0.3231(4) 0.0456(8) Uani 1 1 d . . . . .
H16 H -0.091082 0.649491 0.293105 0.055 Uiso 1 1 calc R U . . .
C17 C -0.0965(3) 0.8487(4) 0.2303(3) 0.0444(7) Uani 1 1 d . . . . .
H17 H -0.084625 0.863078 0.14223 0.053 Uiso 1 1 calc R U . . .
C18 C -0.1091(3) 0.9694(4) 0.2522(3) 0.0414(7) Uani 1 1 d . . . . .
H18 H -0.143604 1.0686 0.17275 0.05 Uiso 1 1 calc R U . . .
C19 C -0.0771(3) 0.9561(3) 0.3728(3) 0.0374(7) Uani 1 1 d . . . . .
H19 H -0.099366 1.047804 0.37122 0.045 Uiso 1 1 calc R U . . .
C20 C 0.9159(3) 0.7722(4) 0.8891(4) 0.0469(8) Uani 1 1 d . . . . .
H20A H 0.993035 0.71616 0.859949 0.056 Uiso 1 1 calc R U . . .
H20B H 0.945745 0.829768 0.916407 0.056 Uiso 1 1 calc R U . . .
Cl1 Cl 0.87737(9) 0.64134(12) 1.03160(9) 0.0526(2) Uani 1 1 d . . . . .
Cl2 Cl 0.77056(10) 0.90041(11) 0.74936(11) 0.0596(3) Uani 1 1 d . . . . .
N1 N 0.4789(2) 0.4085(2) 0.74913(19) 0.0205(4) Uani 1 1 d . . . . .
N2 N 0.4849(2) 0.5933(2) 0.7632(2) 0.0216(4) Uani 1 1 d . . . . .
O1 O 0.18769(19) 0.6412(2) 0.78784(19) 0.0321(4) Uani 1 1 d . . . . .
P1 P 0.17901(6) 0.70728(8) 0.52038(7) 0.02688(18) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
Cl Cl 0.1484 0.1585 '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
N1 C1 N2 108.1(2) . . ?
N1 C1 C12 127.5(2) . . ?
N2 C1 C12 124.3(2) . . ?
C3 C2 N1 107.1(2) . . ?
C3 C2 C7 128.0(2) . . ?
N1 C2 C7 124.9(2) . . ?
C2 C3 N2 107.2(2) . . ?
C2 C3 C8 128.2(2) . . ?
N2 C3 C8 124.6(2) . . ?
N1 C4 C5 112.1(2) . . ?
N1 C4 C6 110.4(2) . . ?
C5 C4 C6 113.9(2) . . ?
N1 C4 H4 106.7 . . ?
C5 C4 H4 106.7 . . ?
C6 C4 H4 106.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 111.7(2) . . ?
N2 C9 C11 111.2(2) . . ?
C10 C9 C11 113.3(2) . . ?
N2 C9 H9 106.7 . . ?
C10 C9 H9 106.7 . . ?
C11 C9 H9 106.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C1 114.9(2) . . ?
O1 C12 P1 132.90(19) . . ?
C1 C12 P1 112.13(16) . . ?
C19 C13 C14 112.4(2) . . ?
C19 C13 P1 110.5(2) . . ?
C14 C13 P1 112.12(19) . . ?
C19 C13 H13 107.2 . . ?
C14 C13 H13 107.2 . . ?
P1 C13 H13 107.2 . . ?
C15 C14 C13 126.7(3) . . ?
C15 C14 H14 116.7 . . ?
C13 C14 H14 116.7 . . ?
C14 C15 C16 126.7(3) . . ?
C14 C15 H15 116.6 . . ?
C16 C15 H15 116.6 . . ?
C17 C16 C15 127.4(3) . . ?
C17 C16 H16 116.3 . . ?
C15 C16 H16 116.3 . . ?
C16 C17 C18 126.1(3) . . ?
C16 C17 H17 116.9 . . ?
C18 C17 H17 116.9 . . ?
C19 C18 C17 126.9(3) . . ?
C19 C18 H18 116.6 . . ?
C17 C18 H18 116.6 . . ?
C18 C19 C13 126.6(3) . . ?
C18 C19 H19 116.7 . . ?
C13 C19 H19 116.7 . . ?
Cl1 C20 Cl2 111.17(18) . . ?
Cl1 C20 H20A 109.4 . . ?
Cl2 C20 H20A 109.4 . . ?
Cl1 C20 H20B 109.4 . . ?
Cl2 C20 H20B 109.4 . . ?
H20A C20 H20B 108 . . ?
C1 N1 C2 108.85(19) . . ?
C1 N1 C4 123.18(19) . . ?
C2 N1 C4 128.0(2) . . ?
C1 N2 C3 108.8(2) . . ?
C1 N2 C9 122.0(2) . . ?
C3 N2 C9 129.2(2) . . ?
C12 P1 C13 99.49(12) . . ?
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
C1 N1 1.344(3) . ?
C1 N2 1.350(3) . ?
C1 C12 1.520(3) . ?
C2 C3 1.359(4) . ?
C2 N1 1.396(3) . ?
C2 C7 1.493(4) . ?
C3 N2 1.392(3) . ?
C3 C8 1.491(3) . ?
C4 N1 1.486(3) . ?
C4 C5 1.518(4) . ?
C4 C6 1.521(4) . ?
C4 H4 1 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 N2 1.483(3) . ?
C9 C10 1.521(4) . ?
C9 C11 1.522(4) . ?
C9 H9 1 . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 O1 1.260(3) . ?
C12 P1 1.737(2) . ?
C13 C19 1.500(4) . ?
C13 C14 1.500(4) . ?
C13 P1 1.880(3) . ?
C13 H13 1 . ?
C14 C15 1.338(4) . ?
C14 H14 0.95 . ?
C15 C16 1.438(5) . ?
C15 H15 0.95 . ?
C16 C17 1.350(5) . ?
C16 H16 0.95 . ?
C17 C18 1.448(5) . ?
C17 H17 0.95 . ?
C18 C19 1.340(5) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 Cl1 1.767(4) . ?
C20 Cl2 1.769(4) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
