Zinc amidinate-catalysed cyclization reaction of carbodiimides and alkynes. An insight into the mechanism.
Parra-Cadenas, Blanca; Ginés, Carlos; García-Vivó, Daniel; Elorriaga, David; Carrillo-Hermosilla, Fernando; Dalton transactions (Cambridge, England : 2003) 53 (2024) 10050–10054; doi:10.1039/d4dt01265h

data_7716185
_publ_section_title
;
 Zinc amidinate-catalysed cyclization reaction of carbodiimides and
 alkynes. An insight into the mechanism.
;
_journal_issue                   24
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10050
_journal_page_last               10054
_journal_paper_doi               10.1039/d4dt01265h
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C43 H50 N2 O2, C6 H6'
_chemical_formula_sum            'C49 H56 N2 O2'
_chemical_formula_weight         704.95
_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             2024-03-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-09 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                102.253(3)
_cell_angle_beta                 97.132(3)
_cell_angle_gamma                103.187(3)
_cell_formula_units_Z            2
_cell_length_a                   9.426(2)
_cell_length_b                   10.912(2)
_cell_length_c                   21.672(5)
_cell_measurement_reflns_used    2072
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.49
_cell_measurement_theta_min      2.26
_cell_volume                     2085.7(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14371
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_min         2.411
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0625 before and 0.0390 after correction.
The Ratio of minimum to maximum transmission is 0.8906.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         7460
_refine_ls_number_restraints     198
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0588
_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^)+(0.0828P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3883
_reflns_number_total             7460
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt01265h2.cif
_cod_data_source_block           bp14_0m
_cod_depositor_comments
'Adding full bibliography for 7716182--7716185.cif.'
_cod_database_code               7716185
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Restrained distances
 C44-C44A \\sim C45-C45A \\sim C46-C46A \\sim C47-C47A \\sim C48-C48A \\sim
C49-C49A
 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
C44 \\sim C44A \\sim C45 \\sim C45A \\sim C46 \\sim C46A \\sim C47 \\sim C47A
\\sim C48 \\sim C48A \\sim C49 \\sim C49A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
3. Others
 Sof(C47A)=Sof(H47A)=Sof(C48A)=Sof(H48A)=Sof(C49A)=Sof(H49A)=Sof(C44A)=
 Sof(H44A)=Sof(C45A)=Sof(H45A)=Sof(C46A)=Sof(H46A)=1-FVAR(1)
 Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=Sof(C46)=Sof(H46)=Sof(C47)=Sof(H47)=
 Sof(C48)=Sof(H48)=Sof(C49)=Sof(H49)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10), C19(H19), C22(H22)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17), C26(H26), C28(H28),
 C31(H31), C32(H32), C34(H34), C35(H35), C38(H38), C39(H39), C41(H41), C42(H42),
  C44(H44), C45(H45), C46(H46), C47(H47), C48(H48), C49(H49), C47A(H47A),
 C48A(H48A), C49A(H49A), C44A(H44A), C45A(H45A), C46A(H46A)
4.c Fitted hexagon refined as free rotating group:
 C44(C45,C46,C47,C48,C49), C47A(C48A,C49A,C44A,C45A,C46A)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C36(H36A,H36B,H36C), C43(H43A,H43B,H43C)
;
_shelx_res_checksum              63970
_olex2_submission_special_instructions 'No special instructions were received'