Enantioselective Amine-Catalyzed [4 + 2] Annulations of Allene Ketones and 2,3-Dioxopyrrolidine Derivatives: Synthesis of 4H-Pyran Derivatives.
Zhang, Shuang; Luo, Yong-Chun; Hu, Xiu-Qin; Wang, Zhu-Yin; Liang, Yong-Min; Xu, Peng-Fei; The Journal of organic chemistry 80 (2015) 7288–7294; doi:10.1021/acs.joc.5b00961

data_4031156
_publ_section_title
;
 Enantioselective Amine-Catalyzed [4 + 2] Annulations of Allene Ketones
 and 2,3-Dioxopyrrolidine Derivatives: Synthesis of 4H-Pyran Derivatives.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7288
_journal_page_last               7294
_journal_paper_doi               10.1021/acs.joc.5b00961
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H23 N O3'
_chemical_formula_sum            'C28 H23 N O3'
_chemical_formula_weight         421.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-19
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Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4796)
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.98554(7)
_cell_length_b                   20.3658(4)
_cell_length_c                   21.6733(3)
_cell_measurement_reflns_used    6841
_cell_measurement_temperature    293.7(2)
_cell_measurement_theta_max      70.4380
_cell_measurement_theta_min      4.3270
_cell_volume                     2200.59(6)
_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      293.7(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1614280000
_diffrn_orient_matrix_UB_12      0.0145677000
_diffrn_orient_matrix_UB_13      0.0590635000
_diffrn_orient_matrix_UB_21      0.2562881000
_diffrn_orient_matrix_UB_22      -0.0084965000
_diffrn_orient_matrix_UB_23      0.0389199000
_diffrn_orient_matrix_UB_31      0.0613895000
_diffrn_orient_matrix_UB_32      0.0737137000
_diffrn_orient_matrix_UB_33      -0.0071709000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
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_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12083
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         70.648
_diffrn_reflns_theta_min         2.977
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61521
_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 dark yellow'
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_extinction_coef       0.0048(6)
_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     290
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0688P)^2^+0.0691P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.639
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                3777
_reflns_number_total             4038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00961_si_002.cif
_cod_data_source_block           zhangshuang0318
_cod_depositor_comments          'Adding full bibliography for 4031156.cif.'
_cod_database_code               4031156
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
;
_shelx_res_checksum              65654
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_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'