Direct oxidative coupling of enamides and 1,3-dicarbonyl compounds: a facile and versatile approach to dihydrofurans, furans, pyrroles, and dicarbonyl enamides.
Li, Pan; Zhao, Jingjing; Xia, Chungu; Li, Fuwei; Organic letters 16 (2014) 5992–5995; doi:10.1021/ol503009f

data_1518195
_publ_section_title
;
 Direct oxidative coupling of enamides and 1,3-dicarbonyl compounds: a
 facile and versatile approach to dihydrofurans, furans, pyrroles, and
 dicarbonyl enamides.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5992
_journal_page_last               5995
_journal_paper_doi               10.1021/ol503009f
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-28
_audit_creation_method
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Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   37.202(3)
_cell_length_b                   8.9299(10)
_cell_length_c                   9.4735(7)
_cell_measurement_reflns_used    1012
_cell_measurement_temperature    294.39(10)
_cell_measurement_theta_max      21.1590
_cell_measurement_theta_min      3.8180
_cell_volume                     3147.2(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      294.39(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -9.00   22.20   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.3571  -99.0000 -150.0000 26

  2 omega    5.00   92.60   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   38.0000  -60.0000 73

  3 omega  -13.00   23.00   1.2000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   19.0000 -120.0000 30
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0107946000
_diffrn_orient_matrix_UB_12      0.0642323000
_diffrn_orient_matrix_UB_13      -0.0119406000
_diffrn_orient_matrix_UB_21      -0.0157056000
_diffrn_orient_matrix_UB_22      -0.0442124000
_diffrn_orient_matrix_UB_23      0.0079017000
_diffrn_orient_matrix_UB_31      -0.0000607000
_diffrn_orient_matrix_UB_32      0.0151854000
_diffrn_orient_matrix_UB_33      0.0735125000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8046
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0022(7)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1662
_refine_ls_R_factor_gt           0.0821
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+1.1797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1846
_refine_ls_wR_factor_ref         0.2311
_reflns_number_gt                1401
_reflns_number_total             3088
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503009f_si_001.cif
_cod_data_source_block           huaws_301_0925
_cod_depositor_comments          'Adding full bibliography for 1518195.cif.'
_cod_database_code               1518195
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'