#------------------------------------------------------------------------------
#$Date: 2024-10-06 10:14:28 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295209 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/24/1572478.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_1572478
loop_
_publ_author_name
'Yoon, Joseph S.'
'Abdellaoui, Mehdi'
'Gembicky, Milan'
'Bertrand, Guy'
_publ_section_title
;
 A carbene-stabilized diphosphorus: a triple-bonded diphosphorus (P[triple
 bond, length as m-dash]P) and a bis(phosphinidene) (P-P) transfer agent.
;
_journal_issue                   38
_journal_name_full               'Chemical science'
_journal_page_first              15713
_journal_page_last               15716
_journal_paper_doi               10.1039/d4sc05091f
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C15 H30 N2 O P2'
_chemical_formula_sum            'C15 H30 N2 O P2'
_chemical_formula_weight         316.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-03
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-03 deposited with the CCDC.	2024-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.366(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7343(6)
_cell_length_b                   11.6579(5)
_cell_length_c                   14.1462(6)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      70.05
_cell_measurement_theta_min      5.10
_cell_volume                     1927.85(15)
_computing_cell_refinement       'SAINT v8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 v2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT v8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker Platinum135 CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Rigaku MicroMax-007HF'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            38129
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         3.781
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.029
_exptl_absorpt_correction_T_max  0.6617
_exptl_absorpt_correction_T_min  0.5063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1536 before and 0.0799 after correction.
The Ratio of minimum to maximum transmission is 0.7652.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0366P)²+0.6323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3121
_reflns_number_total             3469
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc05091f2.cif
_cod_data_source_block           p(co)p
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1572478--1572481.cif.
;
_cod_database_code               1572478
_shelx_shelxl_version_number     2019/1
_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   0.823
_shelx_estimated_absorpt_t_min   0.687
_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 Ternary CH refined with riding coordinates:
 C5(H5), C8(H8), C11(H11), C14(H14)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.61501(3) 0.54374(3) 0.64542(3) 0.02203(10) Uani 1 1 d . . . . .
P2 P 0.76127(3) 0.35660(3) 0.62162(3) 0.02401(11) Uani 1 1 d . . . . .
O1 O 0.80697(8) 0.46400(8) 0.80773(7) 0.0268(2) Uani 1 1 d . . . . .
N1 N 0.56167(10) 0.72113(10) 0.74737(9) 0.0259(3) Uani 1 1 d . . . . .
N2 N 0.91764(10) 0.18028(9) 0.69436(9) 0.0242(2) Uani 1 1 d . . . . .
C1 C 0.74387(11) 0.45714(10) 0.71553(10) 0.0215(3) Uani 1 1 d . . . . .
C2 C 0.62988(12) 0.63606(11) 0.74657(11) 0.0230(3) Uani 1 1 d . . . . .
H2 H 0.6960(14) 0.6253(13) 0.8112(13) 0.028 Uiso 1 1 d . U . . .
C3 C 0.86680(11) 0.27231(11) 0.71105(11) 0.0229(3) Uani 1 1 d . . . . .
H3 H 0.8906(13) 0.2949(13) 0.7814(12) 0.027 Uiso 1 1 d . U . . .
C4 C 0.44960(14) 0.86928(13) 0.62161(12) 0.0360(4) Uani 1 1 d . . . . .
H4A H 0.438475 0.919094 0.672679 0.054 Uiso 1 1 calc R U . . .
H4B H 0.385494 0.879031 0.554814 0.054 Uiso 1 1 calc R U . . .
H4C H 0.521181 0.889846 0.615340 0.054 Uiso 1 1 calc R U . . .
C5 C 0.45528(12) 0.74477(12) 0.65580(11) 0.0278(3) Uani 1 1 d . . . . .
H5 H 0.457038 0.695982 0.598304 0.033 Uiso 1 1 calc R U . . .
C6 C 0.35152(13) 0.70799(14) 0.67656(12) 0.0352(3) Uani 1 1 d . . . . .
H6A H 0.358636 0.626707 0.695744 0.053 Uiso 1 1 calc R U . . .
H6B H 0.281857 0.719580 0.614346 0.053 Uiso 1 1 calc R U . . .
H6C H 0.347358 0.754051 0.732922 0.053 Uiso 1 1 calc R U . . .
C7 C 0.69399(16) 0.86026(14) 0.86919(14) 0.0434(4) Uani 1 1 d . . . . .
H7A H 0.760191 0.808764 0.890438 0.065 Uiso 1 1 calc R U . . .
H7B H 0.702290 0.913087 0.925599 0.065 Uiso 1 1 calc R U . . .
H7C H 0.689487 0.904196 0.808635 0.065 Uiso 1 1 calc R U . . .
C8 C 0.58529(13) 0.78996(13) 0.84261(11) 0.0323(3) Uani 1 1 d . . . . .
H8 H 0.520493 0.845093 0.827546 0.039 Uiso 1 1 calc R U . . .
C9 C 0.58874(16) 0.71435(14) 0.93151(12) 0.0420(4) Uani 1 1 d . . . . .
H9A H 0.516605 0.672041 0.911247 0.063 Uiso 1 1 calc R U . . .
H9B H 0.599477 0.762359 0.991511 0.063 Uiso 1 1 calc R U . . .
H9C H 0.652355 0.659971 0.948998 0.063 Uiso 1 1 calc R U . . .
C10 C 0.98575(14) 0.16802(15) 0.55385(12) 0.0373(4) Uani 1 1 d . . . . .
H10A H 1.002185 0.250400 0.562161 0.056 Uiso 1 1 calc R U . . .
H10B H 0.962790 0.146844 0.481349 0.056 Uiso 1 1 calc R U . . .
H10C H 1.054397 0.124875 0.596150 0.056 Uiso 1 1 calc R U . . .
C11 C 0.88967(13) 0.14011(12) 0.58768(11) 0.0275(3) Uani 1 1 d . . . . .
H11 H 0.820844 0.183977 0.541773 0.033 Uiso 1 1 calc R U . . .
C12 C 0.85769(15) 0.01378(13) 0.57509(13) 0.0387(4) Uani 1 1 d . . . . .
H12A H 0.924926 -0.032465 0.615202 0.058 Uiso 1 1 calc R U . . .
H12B H 0.830547 -0.007356 0.502216 0.058 Uiso 1 1 calc R U . . .
H12C H 0.796963 -0.000303 0.599743 0.058 Uiso 1 1 calc R U . . .
C13 C 1.10514(14) 0.19890(15) 0.84220(13) 0.0405(4) Uani 1 1 d . . . . .
H13A H 1.131275 0.240461 0.795317 0.061 Uiso 1 1 calc R U . . .
H13B H 1.168661 0.154159 0.891037 0.061 Uiso 1 1 calc R U . . .
H13C H 1.078103 0.253814 0.879997 0.061 Uiso 1 1 calc R U . . .
C14 C 1.00817(13) 0.11877(12) 0.78062(11) 0.0294(3) Uani 1 1 d . . . . .
H14 H 1.040681 0.058560 0.749648 0.035 Uiso 1 1 calc R U . . .
C15 C 0.95721(16) 0.05785(15) 0.84797(13) 0.0429(4) Uani 1 1 d . . . . .
H15A H 0.924479 0.114694 0.879553 0.064 Uiso 1 1 calc R U . . .
H15B H 1.017310 0.014632 0.902053 0.064 Uiso 1 1 calc R U . . .
H15C H 0.897096 0.005038 0.805591 0.064 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
C2 P1 C1 96.48(6) . . ?
C3 P2 C1 96.52(6) . . ?
C2 N1 C5 120.54(11) . . ?
C2 N1 C8 120.89(12) . . ?
C5 N1 C8 118.42(11) . . ?
C3 N2 C11 120.09(11) . . ?
C3 N2 C14 121.29(11) . . ?
C11 N2 C14 118.53(10) . . ?
P1 C1 P2 107.15(7) . . ?
O1 C1 P1 126.89(10) . . ?
O1 C1 P2 125.95(10) . . ?
P1 C2 H2 117.6(9) . . ?
N1 C2 P1 127.87(11) . . ?
N1 C2 H2 114.5(9) . . ?
P2 C3 H3 115.9(9) . . ?
N2 C3 P2 128.36(11) . . ?
N2 C3 H3 115.7(9) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C5 C4 H4C 109.5 . . ?
N1 C5 C4 111.50(12) . . ?
N1 C5 H5 107.3 . . ?
N1 C5 C6 109.94(12) . . ?
C4 C5 H5 107.3 . . ?
C4 C5 C6 113.19(12) . . ?
C6 C5 H5 107.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
N1 C8 C7 110.51(12) . . ?
N1 C8 H8 107.4 . . ?
N1 C8 C9 111.34(12) . . ?
C7 C8 H8 107.4 . . ?
C7 C8 C9 112.48(14) . . ?
C9 C8 H8 107.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
N2 C11 C10 110.83(12) . . ?
N2 C11 H11 107.1 . . ?
N2 C11 C12 111.75(12) . . ?
C10 C11 H11 107.1 . . ?
C10 C11 C12 112.55(13) . . ?
C12 C11 H11 107.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
N2 C14 C13 111.30(12) . . ?
N2 C14 H14 107.4 . . ?
N2 C14 C15 110.71(12) . . ?
C13 C14 H14 107.4 . . ?
C13 C14 C15 112.29(13) . . ?
C15 C14 H14 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 C1 1.8451(13) . ?
P1 C2 1.7398(14) . ?
P2 C1 1.8497(13) . ?
P2 C3 1.7388(14) . ?
O1 C1 1.2336(16) . ?
N1 C2 1.3214(17) . ?
N1 C5 1.4824(18) . ?
N1 C8 1.4926(17) . ?
N2 C3 1.3219(17) . ?
N2 C11 1.4823(17) . ?
N2 C14 1.4887(17) . ?
C2 H2 0.974(17) . ?
C3 H3 0.955(16) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C5 1.523(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.524(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C8 1.522(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.522(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C11 1.515(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.519(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C14 1.518(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.524(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
C1 P1 C2 N1 -179.03(13) . . . . ?
C1 P2 C3 N2 178.57(13) . . . . ?
C2 P1 C1 P2 -174.16(7) . . . . ?
C2 P1 C1 O1 6.05(13) . . . . ?
C2 N1 C5 C4 -126.37(14) . . . . ?
C2 N1 C5 C6 107.25(14) . . . . ?
C2 N1 C8 C7 67.31(17) . . . . ?
C2 N1 C8 C9 -58.46(18) . . . . ?
C3 P2 C1 P1 -169.26(7) . . . . ?
C3 P2 C1 O1 10.53(13) . . . . ?
C3 N2 C11 C10 105.63(15) . . . . ?
C3 N2 C11 C12 -127.95(14) . . . . ?
C3 N2 C14 C13 -55.92(18) . . . . ?
C3 N2 C14 C15 69.71(17) . . . . ?
C5 N1 C2 P1 2.5(2) . . . . ?
C5 N1 C8 C7 -117.12(14) . . . . ?
C5 N1 C8 C9 117.11(14) . . . . ?
C8 N1 C2 P1 177.96(11) . . . . ?
C8 N1 C5 C4 58.05(17) . . . . ?
C8 N1 C5 C6 -68.33(16) . . . . ?
C11 N2 C3 P2 2.66(19) . . . . ?
C11 N2 C14 C13 120.68(14) . . . . ?
C11 N2 C14 C15 -113.69(14) . . . . ?
C14 N2 C3 P2 179.21(11) . . . . ?
C14 N2 C11 C10 -71.01(16) . . . . ?
C14 N2 C11 C12 55.40(17) . . . . ?
