Triazolyl-phosphole and triazolyl-azaphosphole: synthesis, transition metal complexes and catalytic studies.
Radhakrishna, Latchupatula; Kote, Basvaraj S.; Gourkhede, Rani; Pandey, Ankit; Kaur, Bhupinder; Balakrishna, Maravanji S.; Dalton transactions (Cambridge, England : 2003) 54 (2025) 2599–2608; doi:10.1039/d4dt03213f

data_7717710
_publ_section_title
;
 Triazolyl-phosphole and triazolyl-azaphosphole: synthesis, transition
 metal complexes and catalytic studies.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2599
_journal_page_last               2608
_journal_paper_doi               10.1039/d4dt03213f
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C20 H14 N3 P'
_chemical_formula_sum            'C20 H14 N3 P'
_chemical_formula_weight         327.31
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-11-05
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2024-11-15 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.743(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9213(8)
_cell_length_b                   8.1536(6)
_cell_length_c                   16.1780(11)
_cell_measurement_reflns_used    5690
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.9780
_cell_measurement_theta_min      2.4990
_cell_volume                     1571.80(19)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -59.00  70.00   0.50   10.00    --  -20.00  72.00-108.00  258
  2  \w    -59.00  47.50   0.50   10.00    --  -20.00  72.00-180.00  213
  3  \w    -40.00 -10.00   0.50   10.00    --  -20.00 -72.00-108.00   60
  4  \w   -110.00  19.00   0.50   10.00    --  -20.00 -72.00 -36.00  258
  5  \w    -51.50  16.00   0.50   10.00    --  -20.00  72.00 108.00  135
  6  \w     34.50  68.50   0.50   10.00    --  -20.00  72.00 -36.00   68
  7  \w    -35.00  -4.00   0.50   10.00    --  -20.00 -72.00-180.00   62
  8  \w    -15.00  15.00   0.50   10.00    --  -20.00 -72.00  36.00   60
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22155
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.222
_diffrn_reflns_theta_min         2.519
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66682
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.123
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4757
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.437
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0767
_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/[\s^2^(Fo^2^)+(0.0719P)^2^+0.9363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.2073
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2709
_reflns_number_total             4757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt03213f2.cif
_cod_data_source_block           compound_2
_cod_depositor_comments
'Adding full bibliography for 7717710--7717712.cif.'
_cod_database_code               7717710
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{C7, N1AA}
{C7A, N1}
3. Restrained distances
 C8-P1 \\sim C8-P1A
 with sigma of 0.02
 P1-C15 \\sim P1A-C15
 with sigma of 0.02
 C10-P1 \\sim C10-P1A
 with sigma of 0.02
 P1-C15 \\sim P1-C15A
 with sigma of 0.02
 C15-C16 \\sim C15A-C16A
 with sigma of 0.02
 C15-C20 \\sim C15A-C20A
 with sigma of 0.02
 C15-P1A \\sim C15A-P1A
 with sigma of 0.02
 C16-C17 \\sim C16A-C17A
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C18-C19 \\sim C18A-C19A
 with sigma of 0.02
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 P1-C16 \\sim P1-C16A
 with sigma of 0.04
 P1-C20 \\sim P1-C20A
 with sigma of 0.04
 C15-C17 \\sim C15A-C17A
 with sigma of 0.04
 C15-C19 \\sim C15A-C19A
 with sigma of 0.04
 C16-C18 \\sim C16A-C18A
 with sigma of 0.04
 C16-C20 \\sim C16A-C20A
 with sigma of 0.04
 C16-P1A \\sim C16A-P1A
 with sigma of 0.04
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
 C18-C20 \\sim C18A-C20A
 with sigma of 0.04
 C20-P1A \\sim C20A-P1A
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(N1AA)
Uanis(N1AA) = Uanis(C7)
Uanis(C7A) = Uanis(N1)
5. Others
 Sof(H10)=Sof(P1A)=1-FVAR(1)
 Sof(H6)=Sof(P1)=FVAR(1)
 Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=1-FVAR(2)
 Sof(C15)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=Sof(C20)=Sof(H20)=FVAR(2)
 Fixed Sof: C7A(0.38925) C7(0.61075) N1AA(0.38925) N1(0.61075)
6.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C2(H2), C10(H10), C11(H11), C3(H3), C12(H12), C6(H6),
 C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C16A(H16A),
 C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A)
6.b Fitted hexagon refined as free rotating group:
 C15(C16,C17,C18,C19,C20), C15A(C16A,C17A,C18A,C19A,C20A)
;
_shelx_res_checksum              96362
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;