Lanthanide-catalyzed deamidative cyclization of secondary amides and ynones through tandem C-H and C-N activation.
Zhang, Junxi; Wang, Yitu; Zhou, Xigeng; Chemical communications (Cambridge, England) 59 (2023) 3253–3256; doi:10.1039/d3cc00216k

data_7131283
_publ_section_title
;
 Lanthanide-catalyzed deamidative cyclization of secondary amides and
 ynones through tandem C-H and C-N activation.
;
_journal_issue                   22
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3253
_journal_page_last               3256
_journal_paper_doi               10.1039/d3cc00216k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C140 N10 O10 Y3'
_chemical_formula_sum            'C140 N10 O10 Y3'
_chemical_formula_weight         2248.23
_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_primary     dual
_audit_creation_date             2022-12-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-10 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                98.237(15)
_cell_angle_beta                 92.972(15)
_cell_angle_gamma                106.495(13)
_cell_formula_units_Z            2
_cell_length_a                   14.227(2)
_cell_length_b                   18.221(4)
_cell_length_c                   26.440(5)
_cell_measurement_reflns_used    9436
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      56.941
_cell_measurement_theta_min      3.058
_cell_volume                     6473(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0863
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            238625
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.438
_diffrn_reflns_theta_min         3.395
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           2.86
_diffrn_source_power             0.1999426
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           69.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.485
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5732
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             2214
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.380
_refine_diff_density_min         -1.130
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1456
_refine_ls_number_reflns         26621
_refine_ls_number_restraints     3243
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1328P)^2^+8.7828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1902
_refine_ls_wR_factor_ref         0.2002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22552
_reflns_number_total             26621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00216k2.cif
_cod_data_source_block           ga_210320b_a
_cod_depositor_comments          'Adding full bibliography for 7131283.cif.'
_cod_database_code               7131283
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.776
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
C77 \\sim C51 \\sim C5 \\sim C6 \\sim C50 \\sim C96 \\sim C7 \\sim C76 \\sim
C97 \\sim C56 \\sim C70 \\sim C4 \\sim C82 \\sim C69 \\sim C3 \\sim C52 \\sim
C101 \\sim C64 \\sim C90 \\sim C57 \\sim C102 \\sim C122 \\sim C31 \\sim C75
\\sim C9 \\sim C100 \\sim C63 \\sim C55 \\sim C37 \\sim C98 \\sim C109 \\sim
C71 \\sim C135 \\sim C8 \\sim C44 \\sim C18 \\sim C116 \\sim C53 \\sim C54
\\sim C89 \\sim C83 \\sim C114 \\sim C85 \\sim C113 \\sim C110 \\sim C65 \\sim
C10 \\sim C121 \\sim C78 \\sim C68 \\sim C103 \\sim C99 \\sim C84 \\sim C136
\\sim C38 \\sim C137 \\sim C115 \\sim C74 \\sim C120 \\sim C66 \\sim C88 \\sim
C72 \\sim C73 \\sim C67 \\sim C81 \\sim C95 \\sim C123 \\sim C94 \\sim C129
\\sim C108 \\sim C36 \\sim C112 \\sim C127 \\sim C25 \\sim C93 \\sim C91 \\sim
C39 \\sim C79 \\sim C33 \\sim C32 \\sim C2 \\sim C138 \\sim C86 \\sim C41 \\sim
C117 \\sim C35 \\sim C40 \\sim C87 \\sim C111 \\sim C80 \\sim C1 \\sim C128
\\sim C119 \\sim C23 \\sim C21 \\sim C140 \\sim C139 \\sim C34 \\sim C58 \\sim
C118 \\sim C22 \\sim C49 \\sim C26 \\sim C107 \\sim C30 \\sim C92 \\sim C28
\\sim C106 \\sim C104 \\sim C27 \\sim C105 \\sim C43 \\sim C45 \\sim C62 \\sim
C130 \\sim C60 \\sim C134 \\sim C46 \\sim C24 \\sim C19 \\sim C124 \\sim C29
\\sim C47 \\sim C126 \\sim C131 \\sim C59 \\sim C20 \\sim C125 \\sim C61 \\sim
C132 \\sim C42 \\sim C133 \\sim C48 \\sim C11 \\sim C12 \\sim C13 \\sim C14
\\sim C15 \\sim C16 \\sim C17: within 3.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 3.8A
Uanis(C12) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
2. Rigid body (RIGU) restrains
 C12, C17, C16, C15, C14, C13, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Fitted hexagon refined as free rotating group:
 C12(C13,C14,C15,C16,C17)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              34109
_shelx_hkl_checksum              89724
_shelx_fab_checksum              58378
_olex2_submission_special_instructions 'No special instructions were received'