#------------------------------------------------------------------------------
#$Date: 2025-08-20 23:21:57 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301837 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/68/4316846.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_4316846
loop_
_publ_author_name
'Alexander N. Kornev'
'Natalia V. Belina'
'Vyacheslav V. Sushev'
'Julia S. Panova'
'Olga V. Lukoyanova'
'Sergey Y. Ketkov'
'Georgy K. Fukin'
'Mikhail A. Lopatin'
'Gleb A. Abakumov'
_publ_section_title
;
 Chemistry of the Phosphorus-Nitrogen Ligands. Multiple Isomeric
 Transformations of the Diphosphinohydrazine Bearing 8-Quinolyl
 Substituent: P\\rightarrowC, P\\rightarrowN, and P\\rightarrowP
 Migrations Caused by Different Factors
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9677
_journal_page_last               9682
_journal_paper_doi               10.1021/ic101410u
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C33 H27 N3 P2'
_chemical_formula_weight         527.52
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.9470(10)
_cell_angle_beta                 112.7310(10)
_cell_angle_gamma                98.9730(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0674(5)
_cell_length_b                   11.7831(6)
_cell_length_c                   12.5396(6)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     1328.11(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8763
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9663
_exptl_absorpt_correction_T_min  0.9482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0719P)²+0.1220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                4443
_reflns_number_total             5765
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic101410u_si_002_2.cif
_cod_data_source_block           pnn3m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1328.10(11)
_cod_database_code               4316846
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P -0.30848(6) 0.27747(5) 0.32448(5) 0.02385(15) Uani 1 1 d . . .
P2 P -0.10981(6) 0.14362(5) 0.26544(5) 0.02628(15) Uani 1 1 d . . .
N1 N -0.1988(2) 0.69322(17) 0.24663(17) 0.0346(4) Uani 1 1 d . . .
N2 N -0.1147(2) 0.51392(19) 0.34838(19) 0.0365(5) Uani 1 1 d . . .
H2A H -0.055(3) 0.582(3) 0.356(2) 0.051(8) Uiso 1 1 d . . .
H2B H -0.079(3) 0.449(2) 0.366(2) 0.045(7) Uiso 1 1 d . . .
N3 N -0.16201(19) 0.25716(16) 0.31791(16) 0.0298(4) Uani 1 1 d . . .
C1 C -0.3070(2) 0.59711(19) 0.22470(19) 0.0273(5) Uani 1 1 d . . .
C2 C -0.2600(2) 0.49928(18) 0.27747(18) 0.0272(5) Uani 1 1 d . . .
C3 C -0.3665(2) 0.39758(18) 0.25643(18) 0.0251(4) Uani 1 1 d . . .
C4 C -0.5175(2) 0.39244(19) 0.18490(18) 0.0292(5) Uani 1 1 d . . .
H4A H -0.5890 0.3229 0.1706 0.035 Uiso 1 1 calc R . .
C5 C -0.5624(2) 0.4849(2) 0.13625(19) 0.0319(5) Uani 1 1 d . . .
H5A H -0.6640 0.4791 0.0888 0.038 Uiso 1 1 calc R . .
C6 C -0.4580(2) 0.5895(2) 0.15638(18) 0.0298(5) Uani 1 1 d . . .
C7 C -0.4960(3) 0.6917(2) 0.1143(2) 0.0381(6) Uani 1 1 d . . .
H7A H -0.5963 0.6920 0.0683 0.046 Uiso 1 1 calc R . .
C8 C -0.3881(3) 0.7892(2) 0.1400(2) 0.0388(6) Uani 1 1 d . . .
H8A H -0.4125 0.8589 0.1144 0.047 Uiso 1 1 calc R . .
C9 C -0.2401(3) 0.7856(2) 0.2050(2) 0.0383(6) Uani 1 1 d . . .
H9A H -0.1658 0.8534 0.2198 0.046 Uiso 1 1 calc R . .
C10 C -0.2780(2) 0.31837(18) 0.47738(18) 0.0266(4) Uani 1 1 d . . .
C11 C -0.1932(2) 0.2596(2) 0.55884(19) 0.0336(5) Uani 1 1 d . . .
H11A H -0.1505 0.2010 0.5339 0.040 Uiso 1 1 calc R . .
C12 C -0.1708(3) 0.2858(2) 0.6760(2) 0.0413(6) Uani 1 1 d . . .
H12A H -0.1158 0.2434 0.7307 0.050 Uiso 1 1 calc R . .
C13 C -0.2281(3) 0.3734(2) 0.7133(2) 0.0431(6) Uani 1 1 d . . .
H13A H -0.2126 0.3912 0.7937 0.052 Uiso 1 1 calc R . .
C14 C -0.3079(3) 0.4353(2) 0.6345(2) 0.0447(6) Uani 1 1 d . . .
H14A H -0.3445 0.4975 0.6610 0.054 Uiso 1 1 calc R . .
C15 C -0.3346(3) 0.4068(2) 0.5162(2) 0.0365(5) Uani 1 1 d . . .
H15A H -0.3919 0.4481 0.4616 0.044 Uiso 1 1 calc R . .
C16 C -0.4634(2) 0.15337(18) 0.25936(18) 0.0248(4) Uani 1 1 d . . .
C17 C -0.5306(2) 0.0989(2) 0.32407(19) 0.0304(5) Uani 1 1 d . . .
H17A H -0.4994 0.1307 0.4054 0.036 Uiso 1 1 calc R . .
C18 C -0.6426(2) -0.0013(2) 0.2709(2) 0.0367(5) Uani 1 1 d . . .
H18A H -0.6871 -0.0382 0.3158 0.044 Uiso 1 1 calc R . .
C19 C -0.6895(2) -0.0476(2) 0.1519(2) 0.0362(5) Uani 1 1 d . . .
H19A H -0.7656 -0.1166 0.1155 0.043 Uiso 1 1 calc R . .
C20 C -0.6253(2) 0.0070(2) 0.0861(2) 0.0354(5) Uani 1 1 d . . .
H20A H -0.6594 -0.0235 0.0041 0.042 Uiso 1 1 calc R . .
C21 C -0.5122(2) 0.1052(2) 0.13926(19) 0.0317(5) Uani 1 1 d . . .
H21A H -0.4668 0.1407 0.0941 0.038 Uiso 1 1 calc R . .
C22 C -0.0461(2) 0.20420(19) 0.16015(18) 0.0273(5) Uani 1 1 d . . .
C23 C -0.0872(3) 0.3039(2) 0.11860(19) 0.0329(5) Uani 1 1 d . . .
H23A H -0.1478 0.3421 0.1458 0.040 Uiso 1 1 calc R . .
C24 C -0.0403(3) 0.3476(2) 0.0380(2) 0.0410(6) Uani 1 1 d . . .
H24A H -0.0693 0.4153 0.0105 0.049 Uiso 1 1 calc R . .
C25 C 0.0482(3) 0.2931(2) -0.0025(2) 0.0437(6) Uani 1 1 d . . .
H25A H 0.0807 0.3236 -0.0572 0.052 Uiso 1 1 calc R . .
C26 C 0.0890(3) 0.1944(3) 0.0372(2) 0.0449(7) Uani 1 1 d . . .
H26A H 0.1496 0.1565 0.0096 0.054 Uiso 1 1 calc R . .
C27 C 0.0415(3) 0.1503(2) 0.1171(2) 0.0380(6) Uani 1 1 d . . .
H27A H 0.0696 0.0817 0.1431 0.046 Uiso 1 1 calc R . .
C28 C 0.0742(2) 0.15614(19) 0.38449(18) 0.0271(5) Uani 1 1 d . . .
C29 C 0.1775(3) 0.2620(2) 0.4315(2) 0.0386(6) Uani 1 1 d . . .
H29A H 0.1536 0.3298 0.4014 0.046 Uiso 1 1 calc R . .
C30 C 0.3144(3) 0.2705(2) 0.5213(2) 0.0406(6) Uani 1 1 d . . .
H30A H 0.3836 0.3437 0.5524 0.049 Uiso 1 1 calc R . .
C31 C 0.3506(3) 0.1726(2) 0.5658(2) 0.0398(6) Uani 1 1 d . . .
H31A H 0.4457 0.1778 0.6261 0.048 Uiso 1 1 calc R . .
C32 C 0.2491(3) 0.0681(2) 0.5227(2) 0.0496(7) Uani 1 1 d . . .
H32A H 0.2727 0.0013 0.5551 0.060 Uiso 1 1 calc R . .
C33 C 0.1112(3) 0.0590(2) 0.4315(2) 0.0395(6) Uani 1 1 d . . .
H33A H 0.0421 -0.0143 0.4013 0.047 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'
N N 0.0061 0.0033 '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
N3 P1 C3 111.30(10) . . ?
N3 P1 C16 115.82(10) . . ?
C3 P1 C16 107.22(10) . . ?
N3 P1 C10 109.48(10) . . ?
C3 P1 C10 106.07(10) . . ?
C16 P1 C10 106.41(10) . . ?
N3 P2 C22 101.27(10) . . ?
N3 P2 C28 101.06(9) . . ?
C22 P2 C28 97.23(9) . . ?
C9 N1 C1 117.3(2) . . ?
P1 N3 P2 134.92(12) . . ?
N1 C1 C6 123.8(2) . . ?
N1 C1 C2 116.33(19) . . ?
C6 C1 C2 119.8(2) . . ?
N2 C2 C3 123.8(2) . . ?
N2 C2 C1 117.4(2) . . ?
C3 C2 C1 118.71(19) . . ?
C2 C3 C4 119.71(19) . . ?
C2 C3 P1 118.66(15) . . ?
C4 C3 P1 121.61(16) . . ?
C5 C4 C3 121.7(2) . . ?
C4 C5 C6 120.2(2) . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 C7 116.3(2) . . ?
C5 C6 C7 123.8(2) . . ?
C8 C7 C6 119.7(2) . . ?
C7 C8 C9 119.2(2) . . ?
N1 C9 C8 123.6(2) . . ?
C15 C10 C11 119.0(2) . . ?
C15 C10 P1 122.47(17) . . ?
C11 C10 P1 118.54(17) . . ?
C12 C11 C10 120.4(2) . . ?
C13 C12 C11 120.0(2) . . ?
C12 C13 C14 120.3(2) . . ?
C13 C14 C15 119.9(2) . . ?
C10 C15 C14 120.4(2) . . ?
C17 C16 C21 118.55(19) . . ?
C17 C16 P1 123.20(16) . . ?
C21 C16 P1 118.12(16) . . ?
C18 C17 C16 120.6(2) . . ?
C17 C18 C19 120.0(2) . . ?
C20 C19 C18 120.0(2) . . ?
C21 C20 C19 120.1(2) . . ?
C20 C21 C16 120.7(2) . . ?
C27 C22 C23 117.7(2) . . ?
C27 C22 P2 120.95(17) . . ?
C23 C22 P2 121.30(16) . . ?
C24 C23 C22 120.8(2) . . ?
C25 C24 C23 120.4(2) . . ?
C26 C25 C24 119.5(2) . . ?
C25 C26 C27 120.1(2) . . ?
C26 C27 C22 121.5(2) . . ?
C33 C28 C29 118.1(2) . . ?
C33 C28 P2 120.07(17) . . ?
C29 C28 P2 121.77(17) . . ?
C30 C29 C28 121.2(2) . . ?
C31 C30 C29 120.0(2) . . ?
C32 C31 C30 119.7(2) . . ?
C31 C32 C33 120.4(2) . . ?
C28 C33 C32 120.5(2) . . ?
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 N3 1.5613(18) . ?
P1 C3 1.799(2) . ?
P1 C16 1.803(2) . ?
P1 C10 1.811(2) . ?
P2 N3 1.6651(18) . ?
P2 C22 1.845(2) . ?
P2 C28 1.845(2) . ?
N1 C9 1.320(3) . ?
N1 C1 1.362(3) . ?
N2 C2 1.356(3) . ?
C1 C6 1.409(3) . ?
C1 C2 1.451(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.423(3) . ?
C4 C5 1.366(3) . ?
C5 C6 1.414(3) . ?
C6 C7 1.421(3) . ?
C7 C8 1.362(4) . ?
C8 C9 1.405(3) . ?
C10 C15 1.387(3) . ?
C10 C11 1.391(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.376(4) . ?
C13 C14 1.378(4) . ?
C14 C15 1.388(3) . ?
C16 C17 1.394(3) . ?
C16 C21 1.402(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.387(3) . ?
C19 C20 1.386(3) . ?
C20 C21 1.377(3) . ?
C22 C27 1.390(3) . ?
C22 C23 1.398(3) . ?
C23 C24 1.388(3) . ?
C24 C25 1.383(4) . ?
C25 C26 1.379(4) . ?
C26 C27 1.386(3) . ?
C28 C33 1.387(3) . ?
C28 C29 1.389(3) . ?
C29 C30 1.381(3) . ?
C30 C31 1.379(3) . ?
C31 C32 1.369(4) . ?
C32 C33 1.394(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661029
2 PubChem 70676648
