#------------------------------------------------------------------------------
#$Date: 2025-01-06 14:28:17 +0200 (Mon, 06 Jan 2025) $
#$Revision: 297116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/73/7717328.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_7717328
loop_
_publ_author_name
'Volk, Niklas'
'García Alcaraz, Antonio'
'Balasubramaniam, Selvakumar'
'Heumann, Jannik'
'Schnakenburg, Gregor'
'Espinosa Ferao, Arturo'
'Streubel, Rainer'
_publ_section_title
;
 Oxaphosphiranes: isolable phosphorus-containing epoxide rings.
;
_journal_issue                   48
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              19351
_journal_page_last               19359
_journal_paper_doi               10.1039/d4dt02915a
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C H2 Cl2, C26 H21 F2 O2 P'
_chemical_formula_sum            'C27 H23 Cl2 F2 O2 P'
_chemical_formula_weight         519.32
_chemical_name_systematic        NV-515
_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             2021-08-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-09-05 deposited with the CCDC.	2024-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                109.434(4)
_cell_angle_beta                 102.726(5)
_cell_angle_gamma                98.471(5)
_cell_formula_units_Z            2
_cell_length_a                   9.9779(6)
_cell_length_b                   10.5830(6)
_cell_length_c                   12.6438(7)
_cell_measurement_reflns_used    6084
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.50
_cell_measurement_theta_min      2.62
_cell_volume                     1192.30(13)
_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
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.981
_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  0.0376
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10912
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         2.625
_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    0.379
_exptl_absorpt_correction_T_max  0.9312
_exptl_absorpt_correction_T_min  0.8054
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.865
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0369
_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)+(0.0461P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3748
_reflns_number_total             5646
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02915a2.cif
_cod_data_source_block           10
_cod_depositor_comments
'Adding full bibliography for 7717326--7717330.cif.'
_cod_original_cell_volume        1192.30(12)
_cod_database_code               7717328
_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   0.956
_shelx_estimated_absorpt_t_min   0.895
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All P(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Cl1 Cl 0.23992(7) 0.97726(6) 0.43511(6) 0.04805(17) Uani 1 1 d . . . . .
Cl2 Cl 0.13251(7) 0.95337(7) 0.62480(6) 0.05112(17) Uani 1 1 d . . . . .
C27 C 0.1960(3) 0.8700(2) 0.5076(2) 0.0415(6) Uani 1 1 d . . . . .
H27A H 0.280752 0.839787 0.537643 0.050 Uiso 1 1 calc R . . . .
H27B H 0.122794 0.786781 0.451412 0.050 Uiso 1 1 calc R . . . .
P P 0.17108(5) 0.41237(5) 0.62901(4) 0.01421(10) Uani 1 1 d . . . . .
H H 0.159(2) 0.283(2) 0.5914(16) 0.017 Uiso 1 1 d R . . . .
F1 F 0.00112(12) 0.12602(12) 0.15922(10) 0.0306(3) Uani 1 1 d . . . . .
F2 F 0.47416(13) 0.12551(14) 0.30574(12) 0.0416(3) Uani 1 1 d . . . . .
O1 O 0.23408(13) 0.58560(12) 0.52100(11) 0.0184(3) Uani 1 1 d . . . . .
H1 H 0.146486 0.563803 0.488411 0.028 Uiso 1 1 calc GR . . . .
O2 O 0.03195(13) 0.44993(13) 0.61227(11) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.27648(18) 0.47198(18) 0.54113(15) 0.0161(3) Uani 1 1 d . . . . .
H1A H 0.378219 0.503832 0.588513 0.019 Uiso 1 1 calc R . . . .
C2 C 0.26318(19) 0.35139(18) 0.43014(15) 0.0177(4) Uani 1 1 d . . . . .
C3 C 0.13457(19) 0.29538(18) 0.34233(15) 0.0198(4) Uani 1 1 d . . . . .
H3 H 0.055299 0.333893 0.349668 0.024 Uiso 1 1 calc R . . . .
C4 C 0.1255(2) 0.1829(2) 0.24477(16) 0.0229(4) Uani 1 1 d . . . . .
C5 C 0.2374(2) 0.1229(2) 0.22923(17) 0.0267(4) Uani 1 1 d . . . . .
H5 H 0.228523 0.044959 0.161075 0.032 Uiso 1 1 calc R . . . .
C6 C 0.3620(2) 0.1823(2) 0.31789(18) 0.0264(4) Uani 1 1 d . . . . .
C7 C 0.3793(2) 0.2952(2) 0.41791(16) 0.0217(4) Uani 1 1 d . . . . .
H7 H 0.467691 0.333591 0.476868 0.026 Uiso 1 1 calc R . . . .
C8 C 0.28022(17) 0.46306(17) 0.78431(14) 0.0149(3) Uani 1 1 d . . . . .
C9 C 0.30007(17) 0.61680(17) 0.85596(15) 0.0152(3) Uani 1 1 d . . . . .
C10 C 0.28880(19) 0.71404(19) 0.80483(16) 0.0205(4) Uani 1 1 d . . . . .
H10 H 0.261655 0.684761 0.721917 0.025 Uiso 1 1 calc R . . . .
C11 C 0.3167(2) 0.85321(19) 0.87346(17) 0.0229(4) Uani 1 1 d . . . . .
H11 H 0.309776 0.918574 0.837331 0.027 Uiso 1 1 calc R . . . .
C12 C 0.35447(19) 0.89726(19) 0.99398(16) 0.0215(4) Uani 1 1 d . . . . .
H12 H 0.372716 0.992611 1.040753 0.026 Uiso 1 1 calc R . . . .
C13 C 0.36566(19) 0.8019(2) 1.04645(16) 0.0219(4) Uani 1 1 d . . . . .
H13 H 0.392289 0.831921 1.129415 0.026 Uiso 1 1 calc R . . . .
C14 C 0.33803(19) 0.66250(19) 0.97798(15) 0.0196(4) Uani 1 1 d . . . . .
H14 H 0.345011 0.597521 1.014517 0.024 Uiso 1 1 calc R . . . .
C15 C 0.19817(18) 0.37551(17) 0.83573(14) 0.0165(3) Uani 1 1 d . . . . .
C16 C 0.06493(19) 0.3947(2) 0.84537(16) 0.0222(4) Uani 1 1 d . . . . .
H16 H 0.026079 0.457994 0.817026 0.027 Uiso 1 1 calc R . . . .
C17 C -0.0114(2) 0.3229(2) 0.89558(18) 0.0286(4) Uani 1 1 d . . . . .
H17 H -0.101514 0.337768 0.901647 0.034 Uiso 1 1 calc R . . . .
C18 C 0.0432(2) 0.2297(2) 0.93695(17) 0.0273(4) Uani 1 1 d . . . . .
H18 H -0.009595 0.179262 0.970157 0.033 Uiso 1 1 calc R . . . .
C19 C 0.1754(2) 0.2110(2) 0.92930(17) 0.0272(4) Uani 1 1 d . . . . .
H19 H 0.213726 0.147634 0.957908 0.033 Uiso 1 1 calc R . . . .
C20 C 0.2530(2) 0.28370(19) 0.88029(16) 0.0208(4) Uani 1 1 d . . . . .
H20 H 0.344477 0.270766 0.877069 0.025 Uiso 1 1 calc R . . . .
C21 C 0.42175(18) 0.42889(18) 0.77016(15) 0.0163(3) Uani 1 1 d . . . . .
C22 C 0.4253(2) 0.29328(19) 0.70734(16) 0.0209(4) Uani 1 1 d . . . . .
H22 H 0.342407 0.221056 0.680881 0.025 Uiso 1 1 calc R . . . .
C23 C 0.5489(2) 0.2633(2) 0.68331(16) 0.0248(4) Uani 1 1 d . . . . .
H23 H 0.549734 0.170954 0.640011 0.030 Uiso 1 1 calc R . . . .
C24 C 0.6708(2) 0.3671(2) 0.72212(17) 0.0271(4) Uani 1 1 d . . . . .
H24 H 0.754812 0.346547 0.704712 0.032 Uiso 1 1 calc R . . . .
C25 C 0.66972(19) 0.5011(2) 0.78636(17) 0.0252(4) Uani 1 1 d . . . . .
H25 H 0.753883 0.572248 0.814619 0.030 Uiso 1 1 calc R . . . .
C26 C 0.54620(18) 0.53211(19) 0.80981(15) 0.0199(4) Uani 1 1 d . . . . .
H26 H 0.546441 0.624676 0.853334 0.024 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'
Cl Cl 0.1484 0.1585 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 C27 Cl2 111.99(12) . . ?
Cl1 C27 H27A 109.2 . . ?
Cl1 C27 H27B 109.2 . . ?
Cl2 C27 H27A 109.2 . . ?
Cl2 C27 H27B 109.2 . . ?
H27A C27 H27B 107.9 . . ?
O2 P H 113.0(8) . . ?
O2 P C1 111.08(7) . . ?
O2 P C8 116.34(7) . . ?
C1 P H 103.6(9) . . ?
C8 P H 100.2(8) . . ?
C8 P C1 111.41(8) . . ?
C1 O1 H1 109.5 . . ?
P C1 H1A 107.9 . . ?
O1 C1 P 109.91(11) . . ?
O1 C1 H1A 107.9 . . ?
O1 C1 C2 113.77(14) . . ?
C2 C1 P 109.32(12) . . ?
C2 C1 H1A 107.9 . . ?
C3 C2 C1 120.00(15) . . ?
C7 C2 C1 119.52(16) . . ?
C7 C2 C3 120.47(16) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.17(16) . . ?
C4 C3 H3 120.9 . . ?
F1 C4 C3 119.05(16) . . ?
F1 C4 C5 117.54(16) . . ?
C3 C4 C5 123.42(18) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 C4 116.21(17) . . ?
C6 C5 H5 121.9 . . ?
F2 C6 C5 117.79(17) . . ?
F2 C6 C7 118.52(18) . . ?
C5 C6 C7 123.69(17) . . ?
C2 C7 H7 121.0 . . ?
C6 C7 C2 118.04(18) . . ?
C6 C7 H7 121.0 . . ?
C9 C8 P 111.70(11) . . ?
C9 C8 C15 109.71(13) . . ?
C9 C8 C21 111.51(14) . . ?
C15 C8 P 105.89(11) . . ?
C15 C8 C21 114.95(14) . . ?
C21 C8 P 102.78(11) . . ?
C10 C9 C8 122.75(15) . . ?
C10 C9 C14 118.40(16) . . ?
C14 C9 C8 118.77(15) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.77(16) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.34(17) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.72(17) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.08(17) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.68(17) . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C8 118.56(15) . . ?
C20 C15 C8 123.48(15) . . ?
C20 C15 C16 117.83(17) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.17(17) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.26(18) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.18(19) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.80(18) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.74(17) . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C8 120.02(16) . . ?
C26 C21 C8 121.56(15) . . ?
C26 C21 C22 118.19(15) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.69(18) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.30(18) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.71(17) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.32(19) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.78(18) . . ?
C25 C26 H26 119.6 . . ?
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
Cl1 C27 1.745(2) . ?
Cl2 C27 1.756(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
P H 1.268(19) . ?
P O2 1.4895(12) . ?
P C1 1.8774(18) . ?
P C8 1.8746(17) . ?
F1 C4 1.352(2) . ?
F2 C6 1.359(2) . ?
O1 H1 0.8400 . ?
O1 C1 1.413(2) . ?
C1 H1A 1.0000 . ?
C1 C2 1.514(2) . ?
C2 C3 1.393(3) . ?
C2 C7 1.393(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(3) . ?
C4 C5 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(3) . ?
C6 C7 1.377(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.534(2) . ?
C8 C15 1.537(2) . ?
C8 C21 1.541(2) . ?
C9 C10 1.391(2) . ?
C9 C14 1.396(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(2) . ?
C15 C20 1.395(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.400(2) . ?
C21 C26 1.396(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.382(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(3) . ?
C26 H26 0.9500 . ?
