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_7720567
_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         'C32 H39 N3, 1.25[C2H6O]'
_chemical_formula_sum            'C34.5 H46.5 N3 O1.25'
_chemical_formula_weight         523.24
_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             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                90
_cell_angle_beta                 137.12(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.217(2)
_cell_length_b                   10.6241(4)
_cell_length_c                   29.473(4)
_cell_measurement_reflns_used    4206
_cell_measurement_temperature    293.15(10)
_cell_measurement_theta_max      68.5630
_cell_measurement_theta_min      2.1690
_cell_volume                     3242.3(19)
_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 0.987
_diffrn_measured_fraction_theta_max 0.851
_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 -11.00   0.50    0.59    --  -87.87  45.00-150.00   72
  2  \w    -64.00 -13.00   0.50    0.59    --  -87.87  61.00 -90.00  102
  3  \w    -48.00 -12.00   0.50    0.59    --  -87.87  45.00   0.00   72
  4  \w    -42.00 -12.00   0.50    0.59    --  -87.87  45.00  60.00   60
  5  \w    -41.00 -11.00   0.50    0.59    --  -87.87  45.00  90.00   60
  6  \w    -44.00 -11.00   0.50    0.59    --  -87.87  45.00  30.00   66
  7  \w   -107.00 -74.00   0.50    0.59    --  -87.87 125.00 -90.00   66
  8  \w    -99.00   8.00   0.50    0.59    --  -51.21 114.00-113.00  214
  9  \w    -51.00 -22.00   0.50    0.59    --  -87.87 125.00 -90.00   58
 10  \w   -106.00 -15.00   0.50    0.59    --  -87.87 114.00-113.00  182
 11  \w   -120.00 -80.00   0.50    0.59    --  -51.21 -77.00-180.00   80
 12  \w   -114.00 -75.00   0.50    0.59    --  -51.21 -77.00-150.00   78
 13  \w   -120.00 -75.00   0.50    0.59    --  -51.21 -77.00 -90.00   90
 14  \w   -160.00 -83.00   0.50    0.59    --  -87.87-114.00 155.00  154
 15  \w   -120.00 -75.00   0.50    0.59    --  -51.21 -77.00 120.00   90
 16  \w     18.00  54.00   0.50    0.59    --   95.43 -45.00  60.00   72
 17  \w     32.00  95.00   0.50    0.59    --   95.43 -77.00 150.00  126
 18  \w     21.00  47.00   0.50    0.59    --   95.43 -45.00 150.00   52
 19  \w     25.00  52.00   0.50    0.59    --   95.43 -45.00  30.00   54
 20  \w     28.00  53.00   0.50    0.59    --   95.43 -45.00 -60.00   50
 21  \w     89.00 168.00   0.50    0.59    --   95.43 114.00-113.00  158
 22  \w     20.00  45.00   0.50    0.59    --   95.43 -45.00-180.00   50
 23  \w     33.00 111.00   0.50    0.59    --   95.43-125.00 -90.00  156
 24  \w     27.00 104.00   0.50    0.59    --   95.43 -95.00 120.00  154
 25  \w     23.00 106.00   0.50    0.59    --   95.43-114.00 155.00  166
 26  \w     -1.00  98.00   0.50    0.59    --   49.59-114.00 155.00  198
;
_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      0.0535765000
_diffrn_orient_matrix_UB_12      -0.1352579000
_diffrn_orient_matrix_UB_13      0.0198317000
_diffrn_orient_matrix_UB_21      -0.1257190000
_diffrn_orient_matrix_UB_22      -0.0478469000
_diffrn_orient_matrix_UB_23      -0.0256224000
_diffrn_orient_matrix_UB_31      -0.0586719000
_diffrn_orient_matrix_UB_32      -0.0208843000
_diffrn_orient_matrix_UB_33      -0.0696639000
_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  0.0787
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            23501
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         81.874
_diffrn_reflns_theta_min         3.174
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.654
_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    1.072
_exptl_crystal_description       block
_exptl_crystal_F_000             1138
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         6127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0720
_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^)+(0.1529P)^2^+0.0291P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2175
_refine_ls_wR_factor_ref         0.2493
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3810
_reflns_number_total             6127
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6dt00276e3.cif
_cod_data_source_block           dipAmpCNH_5
_cod_depositor_comments
'Adding full bibliography for 7720566--7720581.cif.'
_cod_original_cell_volume        3242.5(13)
_cod_original_formula_sum        'C34.50 H46.50 N3 O1.25'
_cod_database_code               7720567
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C11 H10 N O'
_cell_oxdiff_angle_alpha         90.004(4)
_cell_oxdiff_angle_beta          137.107(10)
_cell_oxdiff_angle_gamma         89.984(5)
_cell_oxdiff_length_a            15.2189(11)
_cell_oxdiff_length_b            10.6255(5)
_cell_oxdiff_length_c            29.4598(18)
_cell_oxdiff_measurement_reflns_used 4210
_cell_oxdiff_volume              3242.4(3)
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.916
_diffrn_oxdiff_digest_od_ed
;

;
_diffrn_oxdiff_measurement_exp_name exp_8_DVT408.par
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H2)=1-FVAR(1)
 Sof(H1)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C18(H18), C27(H27), C15(H15), C30(H30)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C7(H7), C4(H4), C6(H6), C13(H13), C11(H11), C12(H12),
 C23(H23), C24(H24), C25(H25)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C31(H31A,H31B,H31C), C29(H29A,H29B,
 H29C), C28(H28A,H28B,H28C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C32(H32A,
 H32B,H32C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              50095
_shelx_hkl_checksum              58894
_shelx_fab_checksum              47134
_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 3.946
_oxdiff_exptl_absorpt_empirical_full_min 0.222