#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:01:15 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298898 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/77/7717711.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_7717711
loop_
_publ_author_name
'Radhakrishna, Latchupatula'
'Kote, Basvaraj S.'
'Gourkhede, Rani'
'Pandey, Ankit'
'Kaur, Bhupinder'
'Balakrishna, Maravanji S.'
_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      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
_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                112.436(4)
_cell_angle_beta                 95.007(3)
_cell_angle_gamma                109.940(4)
_cell_formula_units_Z            2
_cell_length_a                   9.1297(3)
_cell_length_b                   9.3832(4)
_cell_length_c                   11.0431(4)
_cell_measurement_reflns_used    10574
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.9420
_cell_measurement_theta_min      2.0420
_cell_volume                     795.84(7)
_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 1.000
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  25.00   0.50   12.00    --  -20.00   0.00-108.00  270
  2  ω   -110.00  19.00   0.50   12.00    --  -20.00 -72.00-108.00  258
  3  ω    -69.00  19.00   0.50   12.00    --  -20.00 -72.00  36.00  176
  4  ω    -75.50 -12.00   0.50   12.00    --  -20.00 -72.00-180.00  127
  5  ω    -35.00  -5.00   0.50   12.00    --  -20.00 -72.00 -36.00   60
  6  ω   -110.00  70.00   0.50   12.00    --  -20.00   0.00 -36.00  360
  7  ω    -58.50  19.00   0.50   12.00    --  -20.00 -72.00 108.00  155
  8  ω    -59.00  22.00   0.50   12.00    --  -20.00  72.00 -36.00  162
  9  ω    -58.50   4.00   0.50   12.00    --  -20.00  72.00  36.00  125
 10  ω    -44.00 -13.00   0.50   12.00    --  -20.00  72.00-108.00   62
 11  ω    -59.00 -28.50   0.50   12.00    --  -20.00  72.00 108.00   61
 12  ω    -94.00  11.50   0.50   12.00    --  -20.00   0.00  36.00  211
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21476
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.128
_diffrn_reflns_theta_min         2.061
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74727
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
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    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0535
_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)+(0.0551P)²+0.4008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3741
_reflns_number_total             4719
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt03213f2.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
'Adding full bibliography for 7717710--7717712.cif.'
_cod_original_cell_volume        795.83(6)
_cod_database_code               7717711
_shelx_shelxl_version_number     2018/3
_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   0.985
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C17(H17), C18(H18), C16(H16), C19(H19), C14(H14), C13(H13), C4(H4),
 C7(H7), C5(H5), C10(H10), C6(H6), C12(H12), C11(H11)
;
_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
;
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
P1 P 0.62244(5) 0.38196(5) 0.39518(4) 0.02353(12) Uani 1 1 d . . . . .
N1 N 0.83662(16) 0.46934(17) 0.22205(14) 0.0219(3) Uani 1 1 d . . . . .
N3 N 1.00705(17) 0.37392(18) 0.27140(14) 0.0255(3) Uani 1 1 d . . . . .
N2 N 0.97611(17) 0.45117(18) 0.20196(15) 0.0255(3) Uani 1 1 d . . . . .
C15 C 0.44739(19) 0.2029(2) 0.26561(16) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.8526(2) 0.2652(2) 0.42723(16) 0.0243(3) Uani 1 1 d . . . . .
C20 C 0.2964(2) 0.2075(2) 0.26493(17) 0.0249(3) Uani 1 1 d . . . . .
H20 H 0.286905 0.304817 0.327611 0.030 Uiso 1 1 calc R . . . .
C1 C 0.77783(19) 0.40107(19) 0.30444(16) 0.0209(3) Uani 1 1 d . . . . .
C17 C 0.3240(2) -0.0748(2) 0.08021(17) 0.0269(3) Uani 1 1 d . . . . .
H17 H 0.333396 -0.171286 0.016073 0.032 Uiso 1 1 calc R . . . .
C18 C 0.1735(2) -0.0706(2) 0.08134(18) 0.0288(4) Uani 1 1 d . . . . .
H18 H 0.080017 -0.164769 0.018968 0.035 Uiso 1 1 calc R . . . .
C16 C 0.4596(2) 0.0603(2) 0.17167(16) 0.0242(3) Uani 1 1 d . . . . .
H16 H 0.562109 0.056269 0.170795 0.029 Uiso 1 1 calc R . . . .
C2 C 0.88728(19) 0.3422(2) 0.33524(16) 0.0225(3) Uani 1 1 d . . . . .
C9 C 0.77747(19) 0.5557(2) 0.16165(17) 0.0240(3) Uani 1 1 d . . . . .
C19 C 0.1598(2) 0.0707(2) 0.17321(18) 0.0279(4) Uani 1 1 d . . . . .
H19 H 0.057033 0.074042 0.173530 0.033 Uiso 1 1 calc R . . . .
C8 C 0.7113(2) 0.2716(2) 0.46528(17) 0.0262(3) Uani 1 1 d . . . . .
C14 C 0.7984(2) 0.5409(2) 0.03569(18) 0.0288(4) Uani 1 1 d . . . . .
H14 H 0.850645 0.472820 -0.011318 0.035 Uiso 1 1 calc R . . . .
C13 C 0.7421(2) 0.6269(3) -0.0210(2) 0.0350(4) Uani 1 1 d . . . . .
H13 H 0.755456 0.617463 -0.107742 0.042 Uiso 1 1 calc R . . . .
C4 C 0.9382(2) 0.1947(2) 0.47826(18) 0.0295(4) Uani 1 1 d . . . . .
H4 H 1.034559 0.191727 0.453448 0.035 Uiso 1 1 calc R . . . .
C7 C 0.6554(2) 0.2058(3) 0.55322(18) 0.0337(4) Uani 1 1 d . . . . .
H7 H 0.560248 0.210351 0.579679 0.040 Uiso 1 1 calc R . . . .
C5 C 0.8808(2) 0.1286(2) 0.56612(19) 0.0349(4) Uani 1 1 d . . . . .
H5 H 0.938384 0.079940 0.601618 0.042 Uiso 1 1 calc R . . . .
C10 C 0.7020(2) 0.6550(2) 0.2318(2) 0.0329(4) Uani 1 1 d . . . . .
H10 H 0.688141 0.664238 0.318382 0.039 Uiso 1 1 calc R . . . .
C6 C 0.7404(2) 0.1328(3) 0.6025(2) 0.0394(5) Uani 1 1 d . . . . .
H6 H 0.701764 0.085482 0.661632 0.047 Uiso 1 1 calc R . . . .
C12 C 0.6669(3) 0.7260(3) 0.0475(2) 0.0393(5) Uani 1 1 d . . . . .
H12 H 0.628550 0.784493 0.007951 0.047 Uiso 1 1 calc R . . . .
C11 C 0.6470(3) 0.7405(3) 0.1734(2) 0.0419(5) Uani 1 1 d . . . . .
H11 H 0.595457 0.809309 0.220417 0.050 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
C15 P1 C8 100.64(7) . . ?
C1 P1 C15 102.77(7) . . ?
C1 P1 C8 87.13(7) . . ?
N2 N1 C9 119.86(13) . . ?
C1 N1 N2 110.15(13) . . ?
C1 N1 C9 129.96(13) . . ?
N2 N3 C2 107.74(13) . . ?
N3 N2 N1 107.97(13) . . ?
C20 C15 P1 118.57(12) . . ?
C20 C15 C16 119.15(15) . . ?
C16 C15 P1 122.23(12) . . ?
C8 C3 C2 110.05(14) . . ?
C4 C3 C2 129.43(16) . . ?
C4 C3 C8 120.52(15) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.35(15) . . ?
C19 C20 H20 119.8 . . ?
N1 C1 P1 141.68(12) . . ?
N1 C1 C2 104.26(13) . . ?
C2 C1 P1 113.68(12) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.23(16) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.00(16) . . ?
C19 C18 H18 120.0 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.37(15) . . ?
C17 C16 H16 119.8 . . ?
N3 C2 C3 135.10(15) . . ?
N3 C2 C1 109.86(14) . . ?
C1 C2 C3 115.02(14) . . ?
C14 C9 N1 119.57(15) . . ?
C14 C9 C10 121.25(16) . . ?
C10 C9 N1 119.18(15) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 C20 119.90(16) . . ?
C18 C19 H19 120.1 . . ?
C3 C8 P1 113.88(12) . . ?
C7 C8 P1 125.98(14) . . ?
C7 C8 C3 120.06(16) . . ?
C9 C14 H14 120.5 . . ?
C9 C14 C13 118.97(17) . . ?
C13 C14 H14 120.5 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.41(18) . . ?
C12 C13 H13 119.8 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.95(17) . . ?
C5 C4 H4 120.5 . . ?
C8 C7 H7 120.4 . . ?
C8 C7 C6 119.20(18) . . ?
C6 C7 H7 120.4 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.66(17) . . ?
C6 C5 H5 119.7 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.86(18) . . ?
C11 C10 H10 120.6 . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.60(17) . . ?
C5 C6 H6 119.7 . . ?
C13 C12 H12 119.9 . . ?
C13 C12 C11 120.20(17) . . ?
C11 C12 H12 119.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.32(19) . . ?
C12 C11 H11 119.8 . . ?
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 C15 1.8325(17) . ?
P1 C1 1.8057(16) . ?
P1 C8 1.8454(18) . ?
N1 N2 1.3670(18) . ?
N1 C1 1.3497(19) . ?
N1 C9 1.429(2) . ?
N3 N2 1.3112(19) . ?
N3 C2 1.362(2) . ?
C15 C20 1.393(2) . ?
C15 C16 1.394(2) . ?
C3 C2 1.454(2) . ?
C3 C8 1.404(2) . ?
C3 C4 1.388(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.387(2) . ?
C1 C2 1.371(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(2) . ?
C17 C16 1.376(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(3) . ?
C16 H16 0.9500 . ?
C9 C14 1.381(2) . ?
C9 C10 1.387(2) . ?
C19 H19 0.9500 . ?
C8 C7 1.383(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.386(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.378(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(3) . ?
C6 H6 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.379(3) . ?
C11 H11 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
P1 C15 C20 C19 -176.51(12) . . . . ?
P1 C15 C16 C17 176.85(12) . . . . ?
P1 C1 C2 N3 -174.99(11) . . . . ?
P1 C1 C2 C3 4.02(19) . . . . ?
P1 C8 C7 C6 -176.94(15) . . . . ?
N1 C1 C2 N3 -0.50(18) . . . . ?
N1 C1 C2 C3 178.51(13) . . . . ?
N1 C9 C14 C13 -179.27(16) . . . . ?
N1 C9 C10 C11 179.04(17) . . . . ?
N2 N1 C1 P1 172.50(15) . . . . ?
N2 N1 C1 C2 0.65(17) . . . . ?
N2 N1 C9 C14 35.0(2) . . . . ?
N2 N1 C9 C10 -144.12(17) . . . . ?
N2 N3 C2 C3 -178.56(18) . . . . ?
N2 N3 C2 C1 0.16(19) . . . . ?
C15 P1 C1 N1 83.8(2) . . . . ?
C15 P1 C1 C2 -104.78(13) . . . . ?
C15 P1 C8 C3 106.60(13) . . . . ?
C15 P1 C8 C7 -76.63(17) . . . . ?
C15 C20 C19 C18 -0.4(2) . . . . ?
C3 C8 C7 C6 -0.4(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C20 C15 C16 C17 -0.5(2) . . . . ?
C1 P1 C15 C20 -142.69(13) . . . . ?
C1 P1 C15 C16 39.93(15) . . . . ?
C1 P1 C8 C3 4.14(13) . . . . ?
C1 P1 C8 C7 -179.09(17) . . . . ?
C1 N1 N2 N3 -0.58(18) . . . . ?
C1 N1 C9 C14 -147.16(17) . . . . ?
C1 N1 C9 C10 33.8(3) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C17 C16 C15 -0.4(2) . . . . ?
C16 C15 C20 C19 1.0(2) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C2 N3 N2 N1 0.25(17) . . . . ?
C2 C3 C8 P1 -2.81(18) . . . . ?
C2 C3 C8 C7 -179.78(16) . . . . ?
C2 C3 C4 C5 179.79(17) . . . . ?
C9 N1 N2 N3 177.69(14) . . . . ?
C9 N1 C1 P1 -5.6(3) . . . . ?
C9 N1 C1 C2 -177.40(16) . . . . ?
C9 C14 C13 C12 0.2(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C8 P1 C15 C20 127.87(13) . . . . ?
C8 P1 C15 C16 -49.51(14) . . . . ?
C8 P1 C1 N1 -175.9(2) . . . . ?
C8 P1 C1 C2 -4.52(13) . . . . ?
C8 C3 C2 N3 177.94(18) . . . . ?
C8 C3 C2 C1 -0.7(2) . . . . ?
C8 C3 C4 C5 0.8(3) . . . . ?
C8 C7 C6 C5 1.2(3) . . . . ?
C14 C9 C10 C11 0.0(3) . . . . ?
C14 C13 C12 C11 0.0(3) . . . . ?
C13 C12 C11 C10 -0.3(3) . . . . ?
C4 C3 C2 N3 -1.1(3) . . . . ?
C4 C3 C2 C1 -179.78(17) . . . . ?
C4 C3 C8 P1 176.34(13) . . . . ?
C4 C3 C8 C7 -0.6(3) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C10 C9 C14 C13 -0.2(3) . . . . ?
