Iminophosphorano–phosphine based CuI complexes: utility in 1,3-dipolar azide–alkyne cycloaddition and A3-coupling reaction
Gourkhede, Rani; Balakrishna, Maravanji S.; New Journal of Chemistry 49 (2025) 7749–7757; doi:10.1039/D5NJ00379B

data_7063746
_publ_section_title
;
 Iminophosphorano--phosphine based CuI complexes: utility in 1,3-dipolar
 azide--alkyne cycloaddition and A3-coupling reaction
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7749
_journal_page_last               7757
_journal_paper_doi               10.1039/D5NJ00379B
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C16 H16 N O'
_chemical_formula_sum            'C16 H16 N O'
_chemical_formula_weight         238.30
_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     dual
_audit_creation_date             2024-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-24 deposited with the CCDC.	2025-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.874(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5702(7)
_cell_length_b                   9.8185(4)
_cell_length_c                   10.5082(6)
_cell_measurement_reflns_used    4536
_cell_measurement_temperature    290(4)
_cell_measurement_theta_max      26.0160
_cell_measurement_theta_min      2.6100
_cell_volume                     1316.72(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290(4)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -118.01 113.99   0.50    3.00   6.61  -9.84 -31.50    --   464
  2  \w   -100.80  15.70   0.50    3.00    --   -9.84 -59.25 -51.92  233
  3  \w   -100.80  15.70   0.50    3.00    --   -9.84 -59.25  20.08  233
  4  \w   -100.80  15.70   0.50    3.00    --   -9.84 -59.25-123.92  233
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162648000
_diffrn_orient_matrix_UB_12      -0.0662095000
_diffrn_orient_matrix_UB_13      -0.0254797000
_diffrn_orient_matrix_UB_21      -0.0512528000
_diffrn_orient_matrix_UB_22      0.0249527000
_diffrn_orient_matrix_UB_23      -0.0341595000
_diffrn_orient_matrix_UB_31      0.0139941000
_diffrn_orient_matrix_UB_32      0.0144552000
_diffrn_orient_matrix_UB_33      -0.0578068000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21404
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.979
_diffrn_reflns_theta_max         24.979
_diffrn_reflns_theta_min         2.617
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.202
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.560
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0513
_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/[\s^2^(Fo^2^)+(0.0585P)^2^+0.3918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1895
_reflns_number_total             2315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj00379b2.cif
_cod_data_source_block           compound_b23
_cod_depositor_comments
'Adding full bibliography for 7063743--7063746.cif.'
_cod_original_cell_volume        1316.72(12)
_cod_database_code               7063746
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C12-O1 = O1-C11 = C11-C10 = C10-N1 = N1-C13 = C13-C12
 1.39 with sigma of 0.01
 O1-C12
 1.407 with sigma of 0.002
 C12-C11 \\sim O1-C10 \\sim C11-N1 \\sim C10-C13 \\sim N1-C12 \\sim C13-O1
 with sigma of 0.02
3. Restrained planarity
 C12, O1, C11, C10, N1, C13
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.001
5.a Ternary CH refined with riding coordinates:
 C1(H1)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C11(H11A,H11B), C12(H12A,H12B)
5.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C9(H9), C5(H5), C6(H6), C8(H8), C7(H7)
;