Palladium-catalyzed aminoalkynylation/alleneamination of urea-tethered alkenes: access to imidazolidinones bearing alkynes and allenes.
Hu, Qianqian; Hu, Cangzhu; Tang, Tian; Wu, Qing; Hu, Weiming; Dai, Qiang; Wang, Lei; Chemical communications (Cambridge, England) 61 (2025) 17898–17901; doi:10.1039/d5cc04327a

data_7135162
_publ_section_title
;
 Palladium-catalyzed aminoalkynylation/alleneamination of urea-tethered
 alkenes: access to imidazolidinones bearing alkynes and allenes.
;
_journal_issue                   91
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17898
_journal_page_last               17901
_journal_paper_doi               10.1039/d5cc04327a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C20 H20 N2 O'
_chemical_formula_sum            'C20 H20 N2 O'
_chemical_formula_weight         304.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-10-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-07-09 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7180(9)
_cell_length_b                   6.6198(5)
_cell_length_c                   20.0762(17)
_cell_measurement_reflns_used    9733
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.07
_cell_measurement_theta_min      3.08
_cell_volume                     1690.2(2)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0529
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27348
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.204
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1450 before and 0.0605 after correction.
The Ratio of minimum to maximum transmission is 0.8451.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.082
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 939 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     150
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0485P)^2^+0.0680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0890
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2340
_reflns_number_total             2960
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04327a2.cif
_cod_data_source_block           123
_cod_database_code               7135162
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-C24 \\sim C15-C20
 with sigma of 0.02
 C21-C22 \\sim C16-C17
 with sigma of 0.02
 C22-C23 \\sim C17-C18
 with sigma of 0.02
 C23-C25 \\sim C18-C19
 with sigma of 0.02
 C24-C25 \\sim C20-C19
 with sigma of 0.02
 C15-C22 \\sim C15-C17
 with sigma of 0.04
 C15-C25 \\sim C15-C19
 with sigma of 0.04
 C21-C23 \\sim C16-C18
 with sigma of 0.04
 C22-C25 \\sim C17-C19
 with sigma of 0.04
 C23-C24 \\sim C18-C20
 with sigma of 0.04
 C15-C21 \\sim C15-C16
 with sigma of 0.02
 C17-C16 \\sim C22-C21
 with sigma of 0.02
 C18-C17 \\sim C23-C22
 with sigma of 0.02
 C25-C23 \\sim C19-C18
 with sigma of 0.02
 C19-C20 \\sim C25-C24
 with sigma of 0.02
 C15-C20 \\sim C15-C24
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C15 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C15 \\sim C16 \\sim C17 \\sim C18 \\sim C20 \\sim C19: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C15) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18)
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=
 Sof(C20)=Sof(H20)=1-FVAR(1)
 Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=
 Sof(C25)=Sof(H25)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C10(H10)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25), C3(H3), C4(H4)
5.d Fitted hexagon refined as free rotating group:
 C15(C16,C17,C18,C19,C20)
5.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              98942
_shelx_hkl_checksum              56147
_olex2_submission_special_instructions 'No special instructions were received'