Tunable Cu-Ni phosphine-thiolate complexes as water-compatible catalyst for base-free click chemistry
Chaturvedi, Nishtha; Pandey, Vinay Kumar; Tiwari, Vinod K.; Bhattacharya, Subrato; New Journal of Chemistry  (2026) –; doi:10.1039/D5NJ03825A

data_7064205
_publ_section_title
;
 Tunable Cu-Ni phosphine-thiolate complexes as water-compatible catalyst
 for base-free click chemistry
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D5NJ03825A
_journal_year                    2026
_chemical_formula_moiety         'C30 H26 N4 Ni P2 S6, C13 H12 O P'
_chemical_formula_sum            'C43 H38 N4 Ni O P3 S6'
_chemical_formula_weight         970.75
_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
_audit_creation_date             2025-12-09
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-12-09 deposited with the CCDC.	2025-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                96.5250(10)
_cell_angle_beta                 98.9700(10)
_cell_angle_gamma                100.841(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3069(2)
_cell_length_b                   14.2107(3)
_cell_length_c                   20.9064(3)
_cell_measurement_reflns_used    18752
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.8450
_cell_measurement_theta_min      3.1850
_cell_volume                     2368.11(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_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   -113.00 -22.00   0.50    0.41    --  -40.83 -20.00 168.00  182
  2  \w     22.00 113.00   0.50    0.41    --   40.83  20.00 -24.00  182
  3  \w    -31.00  27.00   0.50    0.41    --   40.83 -20.00 168.00  116
  4  \w   -155.00 -64.00   0.50    1.63    --  -82.50 -20.00 168.00  182
  5  \w     77.00 168.00   0.50    1.63    --   96.04  20.00 -24.00  182
  6  \w    -61.00  26.00   0.50    0.41    --  -40.83  54.00  90.00  174
  7  \w    -28.00  31.00   0.50    0.41    --  -40.83  21.00  60.00  118
  8  \w    -27.00  31.00   0.50    0.41    --  -40.83  20.00 -24.00  116
  9  \w     18.00  78.00   0.50    0.41    --   40.83-104.00  90.00  120
 10  \w     18.00  78.00   0.50    0.41    --   40.83-104.00   0.00  120
 11  \w    -35.00  24.00   0.50    0.41    --   40.83 -11.00  60.00  118
 12  \w     41.00 100.00   0.50    0.41    --   40.83-138.00 -90.00  118
 13  \w    -35.00  24.00   0.50    0.41    --   40.83 -11.00-150.00  118
 14  \w     14.00  43.00   0.50    0.41    --   40.83  78.00 -86.10   58
 15  \w      9.00  42.00   0.50    0.41    --   40.83  92.00 -16.58   66
 16  \w    -35.00  24.00   0.50    0.41    --   40.83 -11.00 -60.00  118
 17  \w      8.00  35.00   0.50    0.41    --   40.83  93.00  85.61   54
 18  \w      9.00  42.00   0.50    0.41    --   40.83  92.00-163.23   66
 19  \w      8.00  35.00   0.50    0.41    --   40.83  93.00 -61.31   54
 20  \w    -47.00 -15.00   0.50    1.63    --  -82.50  42.00 120.00   64
 21  \w    -47.00 -15.00   0.50    1.63    --  -82.50  42.00-180.00   64
 22  \w    -47.00 -15.00   0.50    1.63    --  -82.50  42.00-120.00   64
 23  \w    -47.00 -15.00   0.50    1.63    --  -82.50  42.00-150.00   64
 24  \w    -47.00 -15.00   0.50    1.63    --  -82.50  42.00  30.00   64
 25  \w    -47.00 -15.00   0.50    1.63    --  -82.50  42.00 -90.00   64
 26  \w    -47.00 -15.00   0.50    1.63    --  -82.50  42.00   0.00   64
 27  \w    -80.00  -9.00   0.50    1.63    --  -82.50  96.00-120.00  142
 28  \w     71.00 169.00   0.50    1.63    --   96.04  17.00 -90.00  196
 29  \w     99.00 160.00   0.50    1.63    --   96.04 117.00-150.00  122
 30  \w     28.00  83.00   0.50    1.63    --   96.04 -68.00 150.00  110
 31  \w     81.00 164.00   0.50    1.63    --   96.04 145.00 120.00  166
 32  \w     28.00  68.00   0.50    1.63    --   96.04 -59.00 150.00   80
 33  \w     32.00 110.00   0.50    1.63    --   96.04-117.00   0.00  156
 34  \w     32.00 110.00   0.50    1.63    --   96.04-117.00 120.00  156
 35  \w     81.00 166.00   0.50    1.63    --   96.04  25.00  60.00  170
 36  \w     29.00  57.00   0.50    1.63    --   96.04 -50.00-120.00   56
 37  \w     29.00  57.00   0.50    1.63    --   96.04 -50.00 -60.00   56
 38  \w     29.00  57.00   0.50    1.63    --   96.04 -50.00   0.00   56
 39  \w     23.00 106.00   0.50    1.63    --   96.04 -96.00  90.00  166
 40  \w     44.00 127.00   0.50    1.63    --   96.04-145.00-120.00  166
 41  \w     79.00 162.00   0.50    1.63    --   96.04  42.00 -90.00  166
 42  \w     29.00  57.00   0.50    1.63    --   96.04 -50.00 120.00   56
 43  \w     27.00 105.00   0.50    1.63    --   96.04 -77.00-120.00  156
 44  \w     32.00 110.00   0.50    1.63    --   96.04-117.00-120.00  156
 45  \w     23.00 106.00   0.50    1.63    --   96.04 -96.00 120.00  166
 46  \w    105.00 170.00   0.50    1.63    --   96.04  96.00 120.00  130
 47  \w     44.00 127.00   0.50    1.63    --   96.04-145.00 120.00  166
 48  \w     32.00 110.00   0.50    1.63    --   96.04-117.00 -30.00  156
 49  \w     99.00 160.00   0.50    1.63    --   96.04 117.00 150.00  122
 50  \w     28.00  83.00   0.50    1.63    --   96.04 -68.00-150.00  110
 51  \w     72.00 164.00   0.50    1.63    --   96.04  68.00-120.00  184
 52  \w     23.00 106.00   0.50    1.63    --   96.04 -96.00-150.00  166
 53  \w     82.00 164.00   0.50    1.63    --   96.04  33.00 150.00  164
 54  \w     81.00 164.00   0.50    1.63    --   96.04 145.00 150.00  166
 55  \w     28.00  68.00   0.50    1.63    --   96.04 -59.00 120.00   80
 56  \w     27.00 105.00   0.50    1.63    --   96.04 -77.00 120.00  156
 57  \w     28.00  83.00   0.50    1.63    --   96.04 -68.00 -60.00  110
 58  \w   -109.00 -14.00   0.50    0.41    --  -40.83 -77.00 120.00  190
 59  \w   -108.00 -21.00   0.50    0.41    --  -40.83 -54.00   0.00  174
 60  \w     10.00  43.00   0.50    0.41    --   40.83  88.00  25.28   66
 61  \w     21.00 108.00   0.50    0.41    --   40.83  54.00   0.00  174
 62  \w     14.00  43.00   0.50    0.41    --   40.83  79.00 129.01   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1185575000
_diffrn_orient_matrix_UB_12      -0.0705126000
_diffrn_orient_matrix_UB_13      -0.0063424000
_diffrn_orient_matrix_UB_21      -0.1508980000
_diffrn_orient_matrix_UB_22      -0.0857073000
_diffrn_orient_matrix_UB_23      -0.0191498000
_diffrn_orient_matrix_UB_31      -0.0067922000
_diffrn_orient_matrix_UB_32      0.0116706000
_diffrn_orient_matrix_UB_33      -0.0726765000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32342
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.145
_diffrn_reflns_theta_min         2.163
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.316
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             1002
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.053
_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     557
_refine_ls_number_reflns         8551
_refine_ls_number_restraints     86
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0411P)^2^+1.9727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6909
_reflns_number_total             8551
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj03825a2.cif
_cod_data_source_block           ns-96_auto
_cod_original_cell_volume        2368.11(8)
_cod_database_code               7064205
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C H N P Ni S '
_shelx_estimated_absorpt_t_max   0.672
_shelx_estimated_absorpt_t_min   0.564
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C15-C39 = C43-C37 = C42A-C34A
 1.39 with sigma of 0.02
 C39A-C15 = C43A-C37A = C42-C34
 1.39 with sigma of 0.02
 C3-C13 = C13-C23 = C23-C22 = C22-C25 = C25-C19 = C19-C3
 1.39 with sigma of 0.01
 C1-C18 = C18-C28 = C28-C26 = C26-C29 = C29-C20 = C20-C1
 1.39 with sigma of 0.01
 C15-C34 \\sim C15-C34A
 with sigma of 0.02
 C15-C39 \\sim C15-C39A
 with sigma of 0.02
 C34-C42 \\sim C34A-C42A
 with sigma of 0.02
 C37-C42 \\sim C37A-C42A
 with sigma of 0.02
 C37-C43 \\sim C37A-C43A
 with sigma of 0.02
 C39-C43 \\sim C39A-C43A
 with sigma of 0.02
 C15-C42 \\sim C15-C42A
 with sigma of 0.04
 C15-C43 \\sim C15-C43A
 with sigma of 0.04
 C34-C37 \\sim C34A-C37A
 with sigma of 0.04
 C37-C39 \\sim C37A-C39A
 with sigma of 0.04
 C42-C43 \\sim C42A-C43A
 with sigma of 0.04
 C16-C31 \\sim C16-C31A
 with sigma of 0.02
 C16-C32 \\sim C16-C32A
 with sigma of 0.02
 C31-C35 \\sim C31A-C35A
 with sigma of 0.02
 C32-C40 \\sim C32A-C40A
 with sigma of 0.02
 C35-C41 \\sim C35A-C41A
 with sigma of 0.02
 C40-C41 \\sim C40A-C41A
 with sigma of 0.02
 C16-C35 \\sim C16-C35A
 with sigma of 0.04
 C16-C40 \\sim C16-C40A
 with sigma of 0.04
 C31-C41 \\sim C31A-C41A
 with sigma of 0.04
 C32-C41 \\sim C32A-C41A
 with sigma of 0.04
 C35-C40 \\sim C35A-C40A
 with sigma of 0.04
 C12-C24 \\sim C12-C24A
 with sigma of 0.02
 C12-C38 \\sim C12-C38A
 with sigma of 0.02
 C24-C30 \\sim C24A-C30A
 with sigma of 0.02
 C38-C36 \\sim C38A-C36A
 with sigma of 0.02
 C30-C33 \\sim C30A-C33A
 with sigma of 0.02
 C36-C33 \\sim C36A-C33A
 with sigma of 0.02
 C12-C30 \\sim C12-C30A
 with sigma of 0.04
 C12-C36 \\sim C12-C36A
 with sigma of 0.04
 C24-C33 \\sim C24A-C33A
 with sigma of 0.04
 C38-C33 \\sim C38A-C33A
 with sigma of 0.04
 C30-C36 \\sim C30A-C36A
 with sigma of 0.04
 C3-C23 \\sim C13-C22 \\sim C23-C25 \\sim C22-C19 \\sim C25-C3 \\sim C19-C13
 with sigma of 0.02
 C1-C28 \\sim C18-C26 \\sim C28-C29 \\sim C26-C20 \\sim C29-C1 \\sim C20-C18
 with sigma of 0.02
3. Restrained planarity
 C39, C15, C34, C42, C37, C43
 with sigma of 0.1
 C3, C13, C23, C22, C25, C19
 with sigma of 0.1
 C1, C18, C28, C26, C29, C20
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C16) = Uanis(C31) = Uanis(C35) = Uanis(C41) = Uanis(C40) = Uanis(C32)
Uanis(C31A) = Uanis(C35A) = Uanis(C41A) = Uanis(C40A) = Uanis(C32A)
Uanis(C38) = Uanis(C36) = Uanis(C33) = Uanis(C30) = Uanis(C24)
Uanis(C24A) = Uanis(C30A) = Uanis(C33A) = Uanis(C36A) = Uanis(C38A)
5. Others
 Sof(C24A)=Sof(H24A)=Sof(C30A)=Sof(H30A)=Sof(C33A)=Sof(H33A)=Sof(C36A)=
 Sof(H36A)=Sof(C38A)=Sof(H38A)=1-FVAR(1)
 Sof(C24)=Sof(H24)=Sof(C38)=Sof(H38)=Sof(C30)=Sof(H30)=Sof(C36)=Sof(H36)=
 Sof(C33)=Sof(H33)=FVAR(1)
 Fixed Sof: C31(0.45) H31(0.45) C32(0.45) H32(0.45) C34(0.5) H34(0.5)
 C35(0.45) H35(0.45) C37(0.5) H37(0.5) C39(0.5) H39(0.5) C40(0.45) H40(0.45)
 C41(0.45) H41(0.45) C42(0.5) H42(0.5) C43(0.5) H43(0.5) C39A(0.5) H39A(0.5)
 C43A(0.5) H43A(0.5) C37A(0.5) H37A(0.5) C42A(0.5) H42A(0.5) C34A(0.5)
 H34A(0.5) C40A(0.55) H40A(0.55) C41A(0.55) H41A(0.55) C35A(0.55) H35A(0.55)
 C31A(0.55) H31A(0.55) C32A(0.55) H32A(0.55)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B), C11(H11A,H11B)
6.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28),
  C29(H29), C31(H31), C32(H32), C34(H34), C35(H35), C37(H37), C39(H39),
 C40(H40), C41(H41), C42(H42), C43(H43), C39A(H39A), C43A(H43A), C37A(H37A),
 C42A(H42A), C34A(H34A), C40A(H40A), C41A(H41A), C35A(H35A), C31A(H31A),
 C32A(H32A), C24(H24), C38(H38), C30(H30), C36(H36), C33(H33), C24A(H24A),
 C30A(H30A), C33A(H33A), C36A(H36A), C38A(H38A)
;
_shelx_res_checksum              89448
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.832