Palladium-Catalyzed [3+2] Annulation of Allenyl Carbinol Acetates with C,N-Cyclic Azomethine Imines
Guo, Hongchao; Mao, Biming; Zhang, Junya; Xu, Yi; Yan, Zhengyang; Wang, Wei; Wu, Yongjun; Sun, Changqing; Zheng, Bing; Chemical Communications  (2019) –; doi:10.1039/C9CC06670E

data_7124258
_publ_section_title
;
 Palladium-Catalyzed [3+2] Annulation of Allenyl Carbinol Acetates with
 C,N-Cyclic Azomethine Imines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06670E
_journal_year                    2019
_chemical_formula_moiety         'C26 H22 N2 O'
_chemical_formula_sum            'C26 H22 N2 O'
_chemical_formula_weight         378.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2019-06-15 deposited with the CCDC.    2019-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.529(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.884(7)
_cell_length_b                   17.686(5)
_cell_length_c                   12.169(4)
_cell_measurement_reflns_used    5784
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4724
_cell_measurement_theta_min      1.5791
_cell_volume                     4056(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13836
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         1.579
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4631
_refine_ls_number_restraints     296
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0707
_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^)+(0.0348P)^2^+3.1110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4001
_reflns_number_total             4631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06670e2.cif
_cod_data_source_block           mx7088
_cod_database_code               7124258
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C26A-C25 = C26-C25 = C26A-C21A = C26-C21 = C22A-C21A = C22-C21 = C23-C22 =
 C23-C22A
 1.39 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C19A \\sim C20A \\sim C21A \\sim C22A \\sim C26A \\sim C11A \\sim C10A \\sim
N2A \\sim N2 \\sim C10 \\sim C11 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim
C26: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C19A) \\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C21A) \\sim Ueq,
Uanis(C22A) \\sim Ueq, Uanis(C26A) \\sim Ueq, Uanis(C11A) \\sim Ueq,
Uanis(C10A) \\sim Ueq, Uanis(N2A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N2) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq,
Uanis(C26) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H9B)=Sof(H23A)=Sof(H25A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=
 Sof(C21A)=Sof(C22A)=Sof(H22A)=Sof(C26A)=Sof(H26A)=Sof(C11A)=Sof(C10A)=
 Sof(H10A)=Sof(N2A)=1-FVAR(1)
 Sof(N2)=Sof(H9A)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(C19)=Sof(H19)=Sof(C20)=
 Sof(H20)=Sof(C21)=Sof(C22)=Sof(H22)=Sof(H23)=Sof(H25)=Sof(C26)=Sof(H26)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9A), C9(H9B)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C23(H23A),
 C24(H24), C25(H25), C25(H25A), C26(H26), C19A(H19A), C20A(H20A), C22A(H22A),
 C26A(H26A), C10A(H10A)
;
_shelx_res_checksum              67229
_olex2_submission_special_instructions 'No special instructions were received'