Synthesis of 2,3-dihydroquinazolinimines and 1,3-diiminoisoindolines catalyzed by rare earth metal alkyl complexes through tandem addition/cyclization of nitriles with amines.
Guo, Dianjun; He, Jinqiang; Yuan, Qingbing; Zhou, Shuangliu; Zhu, Xiancui; Dalton transactions (Cambridge, England : 2003) 54 (2025) 4484–4492; doi:10.1039/d5dt00106d

data_7718000
_publ_section_title
;
 Synthesis of 2,3-dihydroquinazolinimines and 1,3-diiminoisoindolines
 catalyzed by rare earth metal alkyl complexes through tandem
 addition/cyclization of nitriles with amines.
;
_journal_issue                   11
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4484
_journal_page_last               4492
_journal_paper_doi               10.1039/d5dt00106d
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C41 H54 N5 O Y'
_chemical_formula_sum            'C41 H54 N5 O Y'
_chemical_formula_weight         721.80
_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_block_doi                 10.5517/ccdc.csd.cc2m3c8d
_audit_creation_date             2024-02-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-01-13 deposited with the CCDC.	2025-02-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.2510(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.0772(15)
_cell_length_b                   11.2927(9)
_cell_length_c                   18.0046(15)
_cell_measurement_reflns_used    9269
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.369
_cell_measurement_theta_min      2.170
_cell_volume                     3816.9(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_temperature      293.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32728
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.509
_diffrn_reflns_theta_min         2.105
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.565
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1275 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.5346.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     590
_refine_ls_number_reflns         8725
_refine_ls_number_restraints     785
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0533P)^2^+1.1789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5772
_reflns_number_total             8725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt00106d2.cif
_cod_data_source_block           7b
_cod_depositor_comments
'Adding full bibliography for 7717994--7718001.cif.'
_cod_database_code               7718000
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.745
_shelx_estimated_absorpt_t_min   0.725
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12-C10 = C12A-C10 = C11-C10 = C11A-C10
 1.54 with sigma of 0.01
 C11-C12 = C12A-C11A
 2.515 with sigma of 0.02
 N3-C21A \\sim N3-C21
 with sigma of 0.02
 C21A-C20A \\sim C21-C20
 with sigma of 0.02
 N2-C20 \\sim N2-C20A
 with sigma of 0.02
 Y1-N5A \\sim Y1-N5
 with sigma of 0.02
 N5-C32 \\sim N5A-C32A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C38 \\sim C39 \\sim C40 \\sim C41 \\sim C38A \\sim C39A \\sim C40A \\sim C41A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C11 \\sim C12 \\sim C11A \\sim C12A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N5 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim N5A \\sim
C32A \\sim C33A \\sim C34A \\sim C35A \\sim C36A \\sim C37A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C20 \\sim C21 \\sim C22 \\sim C23 \\sim C20A \\sim C21A \\sim C22A \\sim C24
\\sim C25 \\sim C23A \\sim C24A \\sim C25A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
Uanis(C12A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C10, C11, C12, C11A, C12A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 N5, C32, C33, C34, C36, C37, N5A, C32A, C33A, C34A, C35A, C36A, C37A, Y1, C35
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O1, C38, C39, C40, C41, C38A, C39A, C40A, C41A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 N2, N3, C20, C21, C22, C23, C24, C25, C20A, C21A, C22A, C23A, C24A, C25A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Same fragment restrains
{C22A, C23A, C24A, C25A} sigma for 1-2: 0.02, 1-3: 0.02
as in
{C22, C23, C24, C25}
{O1, C38A, C39A, C40A, C41A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{O1, C38, C39, C40, C41}
6. Others
 Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)=
 Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24C)=
 Sof(H24D)=Sof(C25A)=Sof(H25C)=Sof(H25D)=1-FVAR(1)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=
 Sof(H25A)=Sof(H25B)=FVAR(1)
 Sof(N5A)=Sof(H5AA)=Sof(C32A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34A)=
 Sof(C35A)=Sof(H35A)=Sof(C36A)=Sof(H36A)=Sof(C37A)=Sof(H37A)=1-FVAR(2)
 Sof(N5)=Sof(H5A)=Sof(C32)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=
 Sof(H35)=Sof(C36)=Sof(H36)=Sof(C37)=Sof(H37)=FVAR(2)
 Sof(C38A)=Sof(H38C)=Sof(H38D)=Sof(C39A)=Sof(H39C)=Sof(H39D)=Sof(C40A)=
 Sof(H40C)=Sof(H40D)=Sof(C41A)=Sof(H41C)=Sof(H41D)=1-FVAR(3)
 Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(C40)=Sof(H40A)=
 Sof(H40B)=Sof(C41)=Sof(H41A)=Sof(H41B)=FVAR(3)
 Sof(H10A)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C12A)=Sof(H12D)=
 Sof(H12E)=Sof(H12F)=1-FVAR(4)
 Sof(H10)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12A)=Sof(H12B)=
 Sof(H12C)=FVAR(4)
7.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C10(H10A)
7.b Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C20A(H20C,H20D), C21A(H21C,H21D), C22A(H22C,H22D), C23A(H23C,
 H23D), C24A(H24C,H24D), C25A(H25C,H25D), C38A(H38C,H38D), C39A(H39C,H39D),
 C40A(H40C,H40D), C41A(H41C,H41D)
7.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C3(H3), C4(H4A), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), N5(H5A), C33(H33),
 C34(H34), C35(H35), C36(H36), C37(H37), N5A(H5AA), C33A(H33A), C34A(H34A),
 C35A(H35A), C36A(H36A), C37A(H37A)
7.d Fitted hexagon refined as free rotating group:
 C32(C33,C34,C35,C36,C37), C32A(C33A,C34A,C35A,C36A,C37A)
7.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C11A(H11D,H11E,H11F), C12A(H12D,H12E,H12F)
;
_shelx_res_checksum              68261
_olex2_submission_special_instructions 'No special instructions were received'