Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4-Pyrone, 4-Pyridone, and 3-Pyrrolone Derivatives
Yi-Feng Qiu; Fang Yang; Zi-Hang Qiu; Mei-Jin Zhong; Li-Jing Wang; Yu-Ying Ye; Bo Song; Yong-Min Liang; Journal of Organic Chemistry 78 (2013) 12018–12028; doi:10.1021/jo402055a

data_4028826
_publ_contact_author_name
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;
_publ_section_title
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 Br\/onsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones:
 Selective Synthesis of 4-Pyrone, 4-Pyridone, and 3-Pyrrolone Derivatives
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12018
_journal_page_last               12028
_journal_paper_doi               10.1021/jo402055a
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C24 H17 I2 N O'
_chemical_formula_sum            'C24 H17 I2 N O'
_chemical_formula_weight         589.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-01-09
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.824(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8410(4)
_cell_length_b                   9.5876(4)
_cell_length_c                   22.784(2)
_cell_measurement_reflns_used    3254
_cell_measurement_temperature    291.64(10)
_cell_measurement_theta_max      28.5147
_cell_measurement_theta_min      2.9709
_cell_volume                     2142.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      291.64(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.9740
_diffrn_measurement_details
;
  1 omega  -16.00   10.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000  -90.0000 26

  2 omega   28.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  150.0000 62

  3 omega   72.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867 -178.0000  -30.0000 31

  4 omega  -45.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -19.0000  150.0000 123
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0708177000
_diffrn_orient_matrix_UB_12      -0.0043635000
_diffrn_orient_matrix_UB_13      0.0041819000
_diffrn_orient_matrix_UB_21      0.0161193000
_diffrn_orient_matrix_UB_22      -0.0139106000
_diffrn_orient_matrix_UB_23      0.0303309000
_diffrn_orient_matrix_UB_31      -0.0012651000
_diffrn_orient_matrix_UB_32      0.0726548000
_diffrn_orient_matrix_UB_33      0.0060309000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9258
_diffrn_reflns_theta_full        28.54
_diffrn_reflns_theta_max         28.54
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    2.950
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.827
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.861
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4858
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.3386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                3570
_reflns_number_total             4858
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402055a_si_003.cif
_cod_data_source_block           qiuyf1218
_cod_original_cell_volume        2142.1(3)
_cod_database_code               4028826
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H12A,H12B} of C12, H11 of C11, H10 of C10, H9 of C9, H8 of C8, H7 of C7,
  H14 of C14, H15 of C15, H16 of C16, H17 of C17, H18 of C18, H20 of C20, H21
  of C21, H22 of C22, H23 of C23, H24 of C24
2. Uiso/Uaniso restraints and constraints
Uanis(C14) ~ Ueq, Uanis(C13) ~ Ueq, Uanis(C18) ~ Ueq, Uanis(C17) ~ Ueq, 
Uanis(C16) ~ Ueq, Uanis(C15) ~ Ueq: with sigma of 0.01 and sigma for terminal 
atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;