Transition-metal-free insertion reactions of alkynes into the C-N σ-bonds of imides: synthesis of substituted enamides or chromones.
Zheng, Zhong; Wang, Ye; Xu, Murong; Kong, Lingkai; Wang, Mengdan; Li, Yanzhong; Chemical communications (Cambridge, England) 54 (2018) 6192–6195; doi:10.1039/c8cc03059f

data_7121784
_publ_section_title
;
 Transition-metal-free insertion reactions of alkynes into the C-N
 \s-bonds of imides: synthesis of substituted enamides or chromones.
;
_journal_issue                   48
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6192
_journal_page_last               6195
_journal_paper_doi               10.1039/c8cc03059f
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C29 H21 N O3'
_chemical_formula_sum            'C29 H21 N O3'
_chemical_formula_weight         431.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-06-20 deposited with the CCDC.
2018-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                78.551(2)
_cell_angle_beta                 66.3730(10)
_cell_angle_gamma                74.2780(10)
_cell_formula_units_Z            2
_cell_length_a                   9.7087(8)
_cell_length_b                   10.8041(9)
_cell_length_c                   11.9237(10)
_cell_measurement_reflns_used    4758
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.63
_cell_measurement_theta_min      2.40
_cell_volume                     1097.26(16)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0135
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11232
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.656
_diffrn_reflns_theta_min         1.874
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0329 before and 0.0250 after correction.
The Ratio of minimum to maximum transmission is 0.9161.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         6688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0645P)^2^+0.2770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5421
_reflns_number_total             6688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03059f2.cif
_cod_data_source_block           mo_dm16529_0m
_cod_depositor_comments
'Adding full bibliography for 7121784--7121785.cif.'
_cod_database_code               7121784
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
  C13(H13), C14(H14), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
 C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
;
_shelx_res_checksum              72424
_shelx_hkl_checksum              12756
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'