A novel one-pot method for the synthesis of substituted furopyridines: iodine-mediated oxidation of enaminones by tandem metal-free cyclization.
Yan, Rulong; Li, Xiaoni; Yang, Xiaodong; Kang, Xing; Xiang, Likui; Huang, Guosheng; Chemical communications (Cambridge, England) 51 (2015) 2573–2576; doi:10.1039/c4cc08834d

data_7116467
_publ_section_title
;
 A novel one-pot method for the synthesis of substituted furopyridines:
 iodine-mediated oxidation of enaminones by tandem metal-free cyclization.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2573
_journal_page_last               2576
_journal_paper_doi               10.1039/c4cc08834d
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C20 H14 I N O'
_chemical_formula_sum            'C20 H14 I N O'
_chemical_formula_weight         411.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-04-08
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_audit_update_record
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2014-11-04 deposited with the CCDC.
2015-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.073(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4452(3)
_cell_length_b                   19.3722(6)
_cell_length_c                   11.2423(3)
_cell_measurement_reflns_used    2609
_cell_measurement_temperature    294.64(10)
_cell_measurement_theta_max      26.8140
_cell_measurement_theta_min      3.4490
_cell_volume                     1621.19(9)
_computing_cell_refinement
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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)
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_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)
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_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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.64(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0875661000
_diffrn_orient_matrix_UB_12      0.0057308000
_diffrn_orient_matrix_UB_13      0.0238363000
_diffrn_orient_matrix_UB_21      0.0357342000
_diffrn_orient_matrix_UB_22      -0.0023997000
_diffrn_orient_matrix_UB_23      -0.0578951000
_diffrn_orient_matrix_UB_31      -0.0115413000
_diffrn_orient_matrix_UB_32      0.0361014000
_diffrn_orient_matrix_UB_33      -0.0076595000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6383
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.979
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0377P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                2472
_reflns_number_total             3186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc08834d2.cif
_cod_data_source_block           xianglikui0408
_cod_original_cell_volume        1621.19(10)
_cod_database_code               7116467
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C4(H4), C1(H1), C2(H2), C5(H5), C8(H8), C17(H17), C3(H3), C15(H15),
 C24(H24), C18(H18)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;