#------------------------------------------------------------------------------
#$Date: 2024-03-04 21:48:12 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290082 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/26/7132683.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_7132683
loop_
_publ_author_name
'Gleim, Florian'
'Schnakenburg, Gregor'
'Ferao, Arturo Espinosa'
'Streubel, Rainer'
_publ_section_title
;
 Arbuzov meets 1,2-oxaphosphetanes: transient 1,2-oxaphosphetan-2-iums as
 an entry point to beta-halo phosphane oxides and P-containing oligomers.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2625
_journal_page_last               2628
_journal_paper_doi               10.1039/d4cc00254g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C21 H19 O P'
_chemical_formula_sum            'C21 H19 O P'
_chemical_formula_weight         318.33
_chemical_name_systematic        FLG-326
_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_date             2022-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-08-22 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                94.652(11)
_cell_angle_beta                 90.566(10)
_cell_angle_gamma                113.742(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1143(10)
_cell_length_b                   8.9827(13)
_cell_length_c                   12.4136(16)
_cell_measurement_reflns_used    3259
_cell_measurement_temperature    123
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.49
_cell_volume                     824.6(2)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
 178 frames, detector distance = 100 mm
;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS-2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7553
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         2.488
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.8198
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         7553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.1409
_refine_ls_R_factor_gt           0.0611
_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)+(0.0909P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3639
_reflns_number_total             7553
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00254g2.cif
_cod_data_source_block           6
_cod_depositor_comments
'Adding full bibliography for 7132681--7132686.cif.'
_cod_database_code               7132683
_shelx_shelxl_version_number     2017/1
_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   0.995
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8389(13)
 0.1611(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
P2 P 0.57472(16) 0.73588(15) 0.09200(10) 0.0362(3) Uani 1 1 d . . . . .
O1 O 0.5230(4) 0.8980(4) 0.0928(3) 0.0434(8) Uani 1 1 d . . . . .
C3 C 0.3271(6) 0.6330(6) 0.0985(4) 0.0399(11) Uani 1 1 d . . . . .
H3A H 0.266800 0.551928 0.036321 0.048 Uiso 1 1 calc R . . . .
H3B H 0.285511 0.587724 0.168233 0.048 Uiso 1 1 calc R . . . .
C4 C 0.3272(6) 0.8029(6) 0.0888(4) 0.0479(13) Uani 1 1 d . . . . .
H4A H 0.269031 0.808277 0.019583 0.057 Uiso 1 1 calc R . . . .
H4B H 0.269209 0.837081 0.150071 0.057 Uiso 1 1 calc R . . . .
C5 C 0.6690(6) 0.7471(5) 0.2366(3) 0.0318(10) Uani 1 1 d . . . . .
C6 C 0.5346(5) 0.7462(5) 0.3221(3) 0.0317(10) Uani 1 1 d . . . . .
C7 C 0.4621(6) 0.6196(5) 0.3889(4) 0.0358(10) Uani 1 1 d . . . . .
H7 H 0.499162 0.531631 0.383024 0.043 Uiso 1 1 calc R . . . .
C8 C 0.3363(6) 0.6205(6) 0.4639(4) 0.0396(11) Uani 1 1 d . . . . .
H8 H 0.289263 0.533933 0.509207 0.048 Uiso 1 1 calc R . . . .
C9 C 0.2797(6) 0.7457(6) 0.4731(4) 0.0398(11) Uani 1 1 d . . . . .
H9 H 0.192529 0.745249 0.523701 0.048 Uiso 1 1 calc R . . . .
C10 C 0.3505(6) 0.8722(6) 0.4081(4) 0.0391(11) Uani 1 1 d . . . . .
H10 H 0.311589 0.959013 0.413966 0.047 Uiso 1 1 calc R . . . .
C11 C 0.4774(5) 0.8733(5) 0.3347(4) 0.0349(10) Uani 1 1 d . . . . .
H11 H 0.526814 0.962639 0.291808 0.042 Uiso 1 1 calc R . . . .
C12 C 0.8432(6) 0.9043(5) 0.2519(4) 0.0325(10) Uani 1 1 d . . . . .
C13 C 0.9580(6) 0.9581(5) 0.1676(4) 0.0370(11) Uani 1 1 d . . . . .
H13 H 0.925418 0.898982 0.098154 0.044 Uiso 1 1 calc R . . . .
C14 C 1.1188(6) 1.0957(6) 0.1822(4) 0.0438(12) Uani 1 1 d . . . . .
H14 H 1.194632 1.130105 0.123273 0.053 Uiso 1 1 calc R . . . .
C15 C 1.1687(6) 1.1832(6) 0.2835(4) 0.0421(12) Uani 1 1 d . . . . .
H15 H 1.278509 1.277692 0.294105 0.051 Uiso 1 1 calc R . . . .
C16 C 1.0571(6) 1.1313(5) 0.3686(4) 0.0389(11) Uani 1 1 d . . . . .
H16 H 1.090744 1.189927 0.438156 0.047 Uiso 1 1 calc R . . . .
C17 C 0.8963(6) 0.9939(5) 0.3527(4) 0.0365(11) Uani 1 1 d . . . . .
H17 H 0.820527 0.960123 0.411821 0.044 Uiso 1 1 calc R . . . .
C18 C 0.7169(5) 0.5983(5) 0.2342(3) 0.0308(10) Uani 1 1 d . . . . .
C19 C 0.8799(6) 0.6062(5) 0.2771(4) 0.0361(11) Uani 1 1 d . . . . .
H19 H 0.966366 0.707565 0.309459 0.043 Uiso 1 1 calc R . . . .
C20 C 0.9180(6) 0.4691(6) 0.2734(4) 0.0405(11) Uani 1 1 d . . . . .
H20 H 1.029644 0.477470 0.303773 0.049 Uiso 1 1 calc R . . . .
C21 C 0.7962(6) 0.3204(5) 0.2263(4) 0.0381(11) Uani 1 1 d . . . . .
H21 H 0.823511 0.226875 0.223581 0.046 Uiso 1 1 calc R . . . .
C22 C 0.6340(6) 0.3097(5) 0.1831(4) 0.0376(11) Uani 1 1 d . . . . .
H22 H 0.548651 0.207846 0.150766 0.045 Uiso 1 1 calc R . . . .
C23 C 0.5948(6) 0.4462(5) 0.1866(3) 0.0342(10) Uani 1 1 d . . . . .
H23 H 0.482777 0.436710 0.156101 0.041 Uiso 1 1 calc R . . . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
30 12 -7 0.5673
7 30 -6 0.0312
-7 -30 5 0.0262
-27 30 24 0.7427
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 P2 C3 80.47(18) . . ?
O1 P2 C4 39.12(16) . . ?
O1 P2 C5 104.29(18) . . ?
C3 P2 C4 41.52(18) . . ?
C3 P2 C5 105.5(2) . . ?
C5 P2 C4 112.47(18) . . ?
C4 O1 P2 95.0(3) . . ?
P2 C3 H3A 114.4 . . ?
P2 C3 H3B 114.4 . . ?
H3A C3 H3B 111.5 . . ?
C4 C3 P2 85.8(3) . . ?
C4 C3 H3A 114.4 . . ?
C4 C3 H3B 114.4 . . ?
O1 C4 C3 98.3(3) . . ?
O1 C4 H4A 112.1 . . ?
O1 C4 H4B 112.1 . . ?
C3 C4 H4A 112.1 . . ?
C3 C4 H4B 112.1 . . ?
H4A C4 H4B 109.7 . . ?
C6 C5 P2 112.4(3) . . ?
C6 C5 C12 111.5(3) . . ?
C6 C5 C18 113.1(3) . . ?
C12 C5 P2 106.5(3) . . ?
C18 C5 P2 103.6(3) . . ?
C18 C5 C12 109.3(3) . . ?
C7 C6 C5 122.4(4) . . ?
C11 C6 C5 120.2(4) . . ?
C11 C6 C7 117.4(4) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(4) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.5(4) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 119.3 . . ?
C10 C11 C6 121.4(4) . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C5 121.5(4) . . ?
C13 C12 C17 117.4(4) . . ?
C17 C12 C5 121.0(4) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.7(4) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.4(4) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(5) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.3 . . ?
C16 C17 C12 121.5(4) . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C5 122.9(4) . . ?
C19 C18 C23 117.2(4) . . ?
C23 C18 C5 120.0(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.1(4) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(4) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 119.0(4) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(4) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 119.3 . . ?
C22 C23 C18 121.4(4) . . ?
C22 C23 H23 119.3 . . ?
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
P2 O1 1.670(3) . ?
P2 C3 1.849(4) . ?
P2 C4 2.318(5) . ?
P2 C5 1.923(5) . ?
O1 C4 1.468(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.541(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.528(5) . ?
C5 C12 1.540(6) . ?
C5 C18 1.533(6) . ?
C6 C7 1.398(6) . ?
C6 C11 1.394(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(6) . ?
C12 C17 1.396(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.394(6) . ?
C18 C23 1.402(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.380(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.383(6) . ?
C23 H23 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
P2 O1 C4 C3 5.3(3) . . . . ?
P2 C3 C4 O1 -4.8(3) . . . . ?
P2 C5 C6 C7 115.8(4) . . . . ?
P2 C5 C6 C11 -63.1(5) . . . . ?
P2 C5 C12 C13 -35.9(5) . . . . ?
P2 C5 C12 C17 147.2(4) . . . . ?
P2 C5 C18 C19 133.8(4) . . . . ?
P2 C5 C18 C23 -45.6(4) . . . . ?
O1 P2 C3 C4 4.3(3) . . . . ?
C3 P2 O1 C4 -4.5(3) . . . . ?
C5 P2 O1 C4 -108.2(3) . . . . ?
C5 P2 C3 C4 106.6(3) . . . . ?
C5 C6 C7 C8 -178.3(4) . . . . ?
C5 C6 C11 C10 177.2(4) . . . . ?
C5 C12 C13 C14 -177.2(4) . . . . ?
C5 C12 C17 C16 176.9(4) . . . . ?
C5 C18 C19 C20 180.0(4) . . . . ?
C5 C18 C23 C22 179.9(4) . . . . ?
C6 C5 C12 C13 -158.8(4) . . . . ?
C6 C5 C12 C17 24.3(5) . . . . ?
C6 C5 C18 C19 -104.2(5) . . . . ?
C6 C5 C18 C23 76.4(5) . . . . ?
C6 C7 C8 C9 0.6(7) . . . . ?
C7 C6 C11 C10 -1.7(7) . . . . ?
C7 C8 C9 C10 -0.9(7) . . . . ?
C8 C9 C10 C11 -0.1(7) . . . . ?
C9 C10 C11 C6 1.5(7) . . . . ?
C11 C6 C7 C8 0.7(7) . . . . ?
C12 C5 C6 C7 -124.8(4) . . . . ?
C12 C5 C6 C11 56.3(5) . . . . ?
C12 C5 C18 C19 20.6(6) . . . . ?
C12 C5 C18 C23 -158.8(4) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C13 C12 C17 C16 0.0(7) . . . . ?
C13 C14 C15 C16 0.2(7) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C15 C16 C17 C12 0.4(7) . . . . ?
C17 C12 C13 C14 -0.3(7) . . . . ?
C18 C5 C6 C7 -1.2(6) . . . . ?
C18 C5 C6 C11 179.9(4) . . . . ?
C18 C5 C12 C13 75.4(5) . . . . ?
C18 C5 C12 C17 -101.4(5) . . . . ?
C18 C19 C20 C21 0.5(7) . . . . ?
C19 C18 C23 C22 0.5(6) . . . . ?
C19 C20 C21 C22 -0.4(7) . . . . ?
C20 C21 C22 C23 0.3(7) . . . . ?
C21 C22 C23 C18 -0.4(7) . . . . ?
C23 C18 C19 C20 -0.6(6) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8389(13)
2 0.1611(13)
