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_4028824
_publ_section_title
;
 Br\/onsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones:
 Selective Synthesis of 4-Pyrone, 4-Pyridone, and 3-Pyrrolone Derivatives
;
_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         'C17 H12 O2'
_chemical_formula_sum            'C17 H12 O2'
_chemical_formula_weight         248.27
_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
_audit_creation_date             2013-08-08
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.856(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.8697(14)
_cell_length_b                   5.5982(4)
_cell_length_c                   22.380(3)
_cell_measurement_reflns_used    2213
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4220
_cell_measurement_theta_min      3.7140
_cell_volume                     2593.0(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.8880
_diffrn_measurement_details
;
  1 omega  -85.00  -55.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3700  178.0000 -180.0000 20

  2 omega    6.00   85.50   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   57.0000    0.0000 53

  3 omega  -47.00  -11.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000   90.0000 24

  4 omega    9.00   45.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  -57.0000   90.0000 24

  5 omega   -4.00   95.00   1.5000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   77.0000   60.0000 66
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0300233000
_diffrn_orient_matrix_UB_12      0.0503453000
_diffrn_orient_matrix_UB_13      0.0181733000
_diffrn_orient_matrix_UB_21      -0.0078250000
_diffrn_orient_matrix_UB_22      -0.0202100000
_diffrn_orient_matrix_UB_23      0.0279751000
_diffrn_orient_matrix_UB_31      0.0145813000
_diffrn_orient_matrix_UB_32      -0.1145357000
_diffrn_orient_matrix_UB_33      0.0030755000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11281
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.166
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.298
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0852
_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^)+(0.1480P)^2^+0.6702P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2411
_refine_ls_wR_factor_ref         0.2926
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2750
_reflns_number_total             5080
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo402055a_si_001.cif
_cod_data_source_block           qiuyf0802
_cod_original_cell_volume        2592.9(4)
_cod_database_code               4028824
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C25(H25), C27(H27), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
;
_shelx_res_checksum              71349
_shelxl_version_number           2013-2