Amidines: a deeper look at the archetypal pro-ligand.
de Vere-Tucker, Matthew; Squire, Imogen; Tritto, Michelangelo; Anandkar, Rohil; Syeda, Tayyibah; Uthayan, Divia; Aguila, Gabrielle; Silva de Moraes, Lygia; Bakewell, Clare; Dalton transactions (Cambridge, England : 2003) 55 (2026) 4977–4987; doi:10.1039/d6dt00276e

data_7720570
_publ_section_title
;
 Amidines: a deeper look at the archetypal pro-ligand.
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4977
_journal_page_last               4987
_journal_paper_doi               10.1039/d6dt00276e
_journal_volume                  55
_journal_year                    2026
_chemical_formula_moiety         'C30 H38 N2'
_chemical_formula_sum            'C30 H38 N2'
_chemical_formula_weight         426.62
_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     dual
_audit_creation_date             2026-01-29
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-30 deposited with the CCDC.	2026-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                72.226(3)
_cell_angle_beta                 89.976(2)
_cell_angle_gamma                67.510(3)
_cell_formula_units_Z            4
_cell_length_a                   11.9554(4)
_cell_length_b                   12.4312(5)
_cell_length_c                   20.2934(6)
_cell_measurement_reflns_used    13852
_cell_measurement_temperature    293.15(10)
_cell_measurement_theta_max      75.4720
_cell_measurement_theta_min      2.3160
_cell_volume                     2630.31(18)
_computing_cell_refinement       'CrysAlisPro 1.171.44.118a (Rigaku OD, 2025)'
_computing_data_collection
'CrysAlisPro system (CCD 44.122a 64-bit (release 14-09-2025))'
_computing_data_reduction        'CrysAlisPro 1.171.44.118a (Rigaku OD, 2025)'
_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_environment      air
_diffrn_ambient_temperature      293.15(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_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    -47.00 -10.00   0.50    0.25    --  -87.86  45.00-180.00   74
  2  \w    -75.00 -14.00   0.50    0.25    --  -87.86  65.00 -16.00  122
  3  \w    -98.00 -15.00   0.50    0.25    --  -87.86 125.00  60.00  166
  4  \w    -70.00  22.00   0.50    0.25    --  -51.33  65.00 -16.00  184
  5  \w     26.00  51.00   0.50    0.25    --   56.00  78.00  88.58   50
  6  \w     26.00  51.00   0.50    0.25    --   56.00  78.00  61.98   50
  7  \w     31.00 123.00   0.50    0.25    --   49.58  65.00 -16.00  184
  8  \w     62.00 144.00   0.50    0.25    --  101.75  15.00-119.52  164
  9  \w    103.00 176.00   0.50    0.25    --  101.75  15.00 -77.53  146
 10  \w     59.00 122.00   0.50    0.25    --  101.75  14.00-177.83  126
 11  \w     74.00 102.00   0.50    0.25    --  101.75  15.00 -77.53   56
 12  \w     77.00 169.00   0.50    0.25    --   95.64  65.00 -16.00  184
 13  \w     95.00 129.00   0.50    0.25    --   95.64  45.00 150.00   68
 14  \w     66.00  99.00   0.50    0.25    --  100.00  16.00 144.48   66
 15  \w     64.00 139.00   0.50    0.25    --  101.75  11.00  81.36  150
 16  \w     66.00 135.00   0.50    0.25    --  101.75  14.00  10.16  138
 17  \w     20.00  52.00   0.50    0.25    --   95.64 -45.00 -90.00   64
 18  \w     34.00  65.00   0.50    0.25    --  101.75 -80.00  30.99   62
 19  \w     33.00  59.00   0.50    0.25    --  101.75 -79.00 -26.71   52
 20  \w     38.00  74.00   0.50    0.25    --  101.75 -78.00 -21.21   72
 21  \w     33.00  66.00   0.50    0.25    --  101.75 -77.00 -70.51   66
 22  \w     22.00  80.00   0.50    0.25    --   95.64 -65.00-151.00  116
 23  \w     36.00  78.00   0.50    0.25    --  101.75 -77.00-153.89   84
 24  \w    -24.00  68.00   0.50    0.25    --   49.58 -65.00-151.00  184
 25  \w     21.00  46.00   0.50    0.25    --   95.64 -61.00  30.00   50
 26  \w     33.00  63.00   0.50    0.25    --  101.75 -79.00  66.28   60
 27  \w     34.00  68.00   0.50    0.25    --  101.75 -78.00 152.50   68
 28  \w     -2.00  23.00   0.50    0.25    --   36.00  94.00  38.49   50
 29  \w     18.00  43.00   0.50    0.25    --   95.64 -45.00   0.00   50
 30  \w     20.00  54.00   0.50    0.25    --   95.64 -45.00-180.00   68
 31  \w     35.00  61.00   0.50    0.25    --  101.75 -82.00-119.19   52
 32  \w     76.00 109.00   0.50    0.25    --   95.64-125.00-180.00   66
 33  \w     63.00 111.00   0.50    0.25    --   95.64-125.00 -60.00   96
 34  \w     53.00 109.00   0.50    0.25    --   95.64-125.00-120.00  112
 35  \w     81.00 110.00   0.50    0.25    --   95.64-125.00 -90.00   58
 36  \w     61.00 111.00   0.50    0.25    --   95.64-125.00-150.00  100
 37  \w     49.00  76.00   0.50    0.25    --   95.64-125.00 -90.00   54
 38  \w     77.00 111.00   0.50    0.25    --   95.64-125.00 -30.00   68
 39  \w     58.00 100.00   0.50    0.25    --   95.64 -95.00 -30.00   84
 40  \w     33.00  59.00   0.50    0.25    --  101.75 -90.00 -83.15   52
 41  \w     77.00 104.00   0.50    0.25    --  101.75 -90.00 -83.15   54
 42  \w     35.00  61.00   0.50    0.25    --  101.75 -88.00 -33.29   52
 43  \w     74.00 106.00   0.50    0.25    --  101.75 -88.00  16.42   64
 44  \w     82.00 111.00   0.50    0.25    --   95.64-125.00  60.00   58
 45  \w     82.00 108.00   0.50    0.25    --   95.64-125.00 120.00   52
 46  \w     39.00  77.00   0.50    0.25    --  101.75 -87.00 116.98   76
 47  \w     26.00  58.00   0.50    0.25    --   95.64-125.00  60.00   64
 48  \w     80.00 105.00   0.50    0.25    --  101.75 -87.00 116.98   50
 49  \w     37.00  70.00   0.50    0.25    --  101.75 -88.00  16.42   66
 50  \w     34.00  98.00   0.50    0.25    --  101.75 -86.00  93.36  128
 51  \w     77.00 107.00   0.50    0.25    --  101.75 -88.00 -33.29   60
 52  \w     34.00  62.00   0.50    0.25    --  101.75 -88.00-102.22   56
 53  \w     81.00 108.00   0.50    0.25    --  101.75 -87.00-137.61   54
 54  \w     37.00  96.00   0.50    0.25    --  101.75 -87.00-165.33  118
 55  \w     78.00 104.00   0.50    0.25    --  101.75 -86.00 -78.98   52
 56  \w     35.00  73.00   0.50    0.25    --  101.75 -86.00 -78.98   76
 57  \w     71.00 102.00   0.50    0.25    --  101.75 -86.00  52.77   62
 58  \w     34.00  68.00   0.50    0.25    --  101.75 -86.00  52.77   68
 59  \w     54.00  80.00   0.50    0.25    --  101.75 -86.00 135.04   52
 60  \w     74.00 101.00   0.50    0.25    --  101.75 -85.00 146.34   54
 61  \w     38.00  97.00   0.50    0.25    --  101.75 -86.00 175.43  118
 62  \w     33.00  70.00   0.50    0.25    --  101.75 -85.00 146.34   74
 63  \w   -125.00 -32.00   0.50    0.25    --  -51.33 -65.00-151.00  186
 64  \w   -168.00 -85.00   0.50    0.25    --  -96.00 -53.00 -77.62  166
 65  \w   -161.00 -69.00   0.50    0.25    --  -87.86 -65.00-151.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0158275000
_diffrn_orient_matrix_UB_12      -0.1319590000
_diffrn_orient_matrix_UB_13      0.0065814000
_diffrn_orient_matrix_UB_21      -0.1037573000
_diffrn_orient_matrix_UB_22      0.0524502000
_diffrn_orient_matrix_UB_23      -0.0606969000
_diffrn_orient_matrix_UB_31      0.0937035000
_diffrn_orient_matrix_UB_32      -0.0053153000
_diffrn_orient_matrix_UB_33      -0.0523541000
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            54476
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.092
_diffrn_reflns_theta_min         2.307
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.283
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.44.118a (Rigaku Oxford Diffraction, 2025)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.077
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: petroleum ether (40-60 C)'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.041
_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     580
_refine_ls_number_reflns         10832
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0938
_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^)+(0.0818P)^2^+1.9170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2392
_refine_ls_wR_factor_ref         0.2450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9032
_reflns_number_total             10832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6dt00276e3.cif
_cod_data_source_block           depAmmesH_20
_cod_depositor_comments
'Adding full bibliography for 7720566--7720581.cif.'
_cod_original_cell_volume        2630.31(17)
_cod_database_code               7720570
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C60 H78 N4'
_cell_oxdiff_angle_alpha         72.226(3)
_cell_oxdiff_angle_beta          89.976(2)
_cell_oxdiff_angle_gamma         67.510(3)
_cell_oxdiff_length_a            11.9554(4)
_cell_oxdiff_length_b            12.4312(5)
_cell_oxdiff_length_c            20.2934(6)
_cell_oxdiff_measurement_reflns_used 13867
_cell_oxdiff_volume              2630.30(15)
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.800
_diffrn_oxdiff_digest_od_ed
;

;
_diffrn_oxdiff_measurement_exp_name exp_6_DVT419_fullexp.par
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C48-C49 \\sim C48-C49A
 with sigma of 0.02
 C27-C28 \\sim C27-C28A
 with sigma of 0.02
 C41-C46 \\sim C41-C46A
 with sigma of 0.02
 C46-C47 \\sim C46A-C47A
 with sigma of 0.02
 C41-C47 \\sim C41-C47A
 with sigma of 0.04
 C32-C37 \\sim C32A-C37A
 with sigma of 0.02
 C32-C33 \\sim C32A-C33A
 with sigma of 0.02
 C36-C35 \\sim C36A-C35A
 with sigma of 0.02
 C36-C39 \\sim C36A-C39A
 with sigma of 0.02
 C33-C34 \\sim C33A-C34A
 with sigma of 0.02
 C35-C34 \\sim C35A-C34A
 with sigma of 0.02
 C34-C38 \\sim C34A-C38A
 with sigma of 0.02
 C78-C32 \\sim C78-C32A
 with sigma of 0.04
 C78-C36 \\sim C78-C36A
 with sigma of 0.04
 C32-C36 \\sim C32A-C36A
 with sigma of 0.04
 C32-C34 \\sim C32A-C34A
 with sigma of 0.04
 C36-C34 \\sim C36A-C34A
 with sigma of 0.04
 C37-C33 \\sim C37A-C33A
 with sigma of 0.04
 C33-C35 \\sim C33A-C35A
 with sigma of 0.04
 C33-C38 \\sim C33A-C38A
 with sigma of 0.04
 C35-C39 \\sim C35A-C39A
 with sigma of 0.04
 C35-C38 \\sim C35A-C38A
 with sigma of 0.04
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C3-C8 \\sim C3A-C8A
 with sigma of 0.02
 C7-C6 \\sim C7A-C6A
 with sigma of 0.02
 C7-C10 \\sim C7A-C10A
 with sigma of 0.02
 C4-C5 \\sim C4A-C5A
 with sigma of 0.02
 C6-C5 \\sim C6A-C5A
 with sigma of 0.02
 C5-C9 \\sim C5A-C9A
 with sigma of 0.02
 C1-C3 \\sim C1-C3A
 with sigma of 0.04
 C1-C7 \\sim C1-C7A
 with sigma of 0.04
 C3-C7 \\sim C3A-C7A
 with sigma of 0.04
 C3-C5 \\sim C3A-C5A
 with sigma of 0.04
 C7-C5 \\sim C7A-C5A
 with sigma of 0.04
 C4-C6 \\sim C4A-C6A
 with sigma of 0.04
 C4-C8 \\sim C4A-C8A
 with sigma of 0.04
 C4-C9 \\sim C4A-C9A
 with sigma of 0.04
 C6-C10 \\sim C6A-C10A
 with sigma of 0.04
 C6-C9 \\sim C6A-C9A
 with sigma of 0.04
 C58-C59 \\sim C58-C71
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C49) = Uanis(C49A)
Uanis(C28) = Uanis(C28A)
Uanis(C46A) = Uanis(C46) = Uanis(C47A) = Uanis(C47)
Uanis(C32A) = Uanis(C32) = Uanis(C37A) = Uanis(C37) = Uanis(C33A) = Uanis(C33)
= Uanis(C34) = Uanis(C34A) = Uanis(C38) = Uanis(C38A) = Uanis(C35) =
Uanis(C35A) = Uanis(C36) = Uanis(C36A) = Uanis(C39) = Uanis(C39A)
Uanis(C10A) = Uanis(C10) = Uanis(C7A) = Uanis(C7) = Uanis(C6) = Uanis(C6A) =
Uanis(C5) = Uanis(C5A) = Uanis(C9) = Uanis(C9A) = Uanis(C4) = Uanis(C4A) =
Uanis(C3) = Uanis(C3A) = Uanis(C8) = Uanis(C8A)
Uanis(C59) = Uanis(C71)
4. Others
 Sof(H48c)=Sof(H48d)=Sof(C49A)=Sof(H49d)=Sof(H49e)=Sof(H49f)=1-FVAR(1)
 Sof(H48a)=Sof(H48b)=Sof(C49)=Sof(H49a)=Sof(H49b)=Sof(H49c)=FVAR(1)
 Sof(H3)=Sof(H27c)=Sof(H27d)=Sof(C28A)=Sof(H28d)=Sof(H28e)=Sof(H28f)=1-FVAR(2)
 Sof(H4)=Sof(H27a)=Sof(H27b)=Sof(C28)=Sof(H28a)=Sof(H28b)=Sof(H28c)=FVAR(2)
 Sof(H2)=Sof(C46A)=Sof(H46c)=Sof(H46d)=Sof(C47A)=Sof(H47d)=Sof(H47e)=Sof(H47f)=
 1-FVAR(3)
 Sof(H1)=Sof(C46)=Sof(H46a)=Sof(H46b)=Sof(C47)=Sof(H47a)=Sof(H47b)=Sof(H47c)=
 FVAR(3)
 Sof(C37A)=Sof(H37d)=Sof(H37e)=Sof(H37f)=Sof(C32A)=Sof(C36A)=Sof(C39A)=
 Sof(H39d)=Sof(H39e)=Sof(H39f)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(C35A)=
 Sof(H35A)=Sof(C38A)=Sof(H38d)=Sof(H38e)=Sof(H38f)=1-FVAR(4)
 Sof(C32)=Sof(C36)=Sof(C37)=Sof(H37a)=Sof(H37b)=Sof(H37c)=Sof(C33)=Sof(H33)=
 Sof(C35)=Sof(H35)=Sof(C34)=Sof(C39)=Sof(H39a)=Sof(H39b)=Sof(H39c)=Sof(C38)=
 Sof(H38a)=Sof(H38b)=Sof(H38c)=FVAR(4)
 Sof(C10A)=Sof(H10d)=Sof(H10e)=Sof(H10f)=Sof(C7A)=Sof(C3A)=Sof(C8A)=Sof(H8Aa)=
 Sof(H8Ab)=Sof(H8Ac)=Sof(C6A)=Sof(H6A)=Sof(C5A)=Sof(C4A)=Sof(H4Aa)=Sof(C9A)=
 Sof(H9Aa)=Sof(H9Ab)=Sof(H9Ac)=1-FVAR(5)
 Sof(C3)=Sof(C7)=Sof(C4)=Sof(H4a)=Sof(C6)=Sof(H6)=Sof(C5)=Sof(C8)=Sof(H8a)=
 Sof(H8b)=Sof(H8c)=Sof(C10)=Sof(H10a)=Sof(H10b)=Sof(H10c)=Sof(C9)=Sof(H9a)=
 Sof(H9b)=Sof(H9c)=FVAR(5)
 Sof(H58c)=Sof(H58d)=Sof(C71)=Sof(H71a)=Sof(H71b)=Sof(H71c)=1-FVAR(6)
 Sof(H58a)=Sof(H58b)=Sof(C59)=Sof(H59a)=Sof(H59b)=Sof(H59c)=FVAR(6)
5.a Secondary CH2 refined with riding coordinates:
 C56(H56a,H56b), C17(H17a,H17b), C19(H19a,H19b), C58(H58c,H58d), C58(H58a,
 H58b), C29(H29a,H29b), C48(H48a,H48b), C48(H48c,H48d), C27(H27a,H27b),
 C27(H27c,H27d), C46(H46a,H46b), C46A(H46c,H46d)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), N3(H3), N2(H2), C52(H52), C4(H4a), C6(H6), C15(H15), C33(H33),
  C13(H13), C54(H54), C53(H53), C35(H35), C14(H14), C42(H42), C23(H23),
 C44(H44), C24(H24), C43(H43), C25(H25), C33A(H33A), C35A(H35A), C6A(H6A),
 C4A(H4Aa)
5.c Idealised Me refined as rotating group:
 C37(H37a,H37b,H37c), C57(H57a,H57b,H57c), C8(H8a,H8b,H8c), C10(H10a,H10b,
 H10c), C39(H39a,H39b,H39c), C20(H20a,H20b,H20c), C18(H18a,H18b,H18c), C9(H9a,
 H9b,H9c), C38(H38a,H38b,H38c), C47(H47a,H47b,H47c), C59(H59a,H59b,H59c),
 C49(H49a,H49b,H49c), C30(H30a,H30b,H30c), C28(H28a,H28b,H28c), C49A(H49d,H49e,
 H49f), C28A(H28d,H28e,H28f), C47A(H47d,H47e,H47f), C37A(H37d,H37e,H37f),
 C39A(H39d,H39e,H39f), C38A(H38d,H38e,H38f), C10A(H10d,H10e,H10f), C8A(H8Aa,
 H8Ab,H8Ac), C9A(H9Aa,H9Ab,H9Ac), C71(H71a,H71b,H71c)
;
_shelx_res_checksum              95881
_shelx_hkl_checksum              41446
_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 2.669
_oxdiff_exptl_absorpt_empirical_full_min 0.492