Asymmetric direct vinylogous Michael addition to 2-enoylpyridine N-oxides catalyzed by bifunctional thio-urea.
Rout, Subhrajit; Ray, Sumit K.; Unhale, Rajshekhar A.; Singh, Vinod K.; Organic letters 16 (2014) 5568–5571; doi:10.1021/ol5025794

data_1518013
_publ_section_title
;
 Asymmetric direct vinylogous Michael addition to 2-enoylpyridine N-oxides
 catalyzed by bifunctional thio-urea.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5568
_journal_page_last               5571
_journal_paper_doi               10.1021/ol5025794
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C28 H25 N3 O3 S'
_chemical_formula_weight         483.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 98.979(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   5.844(5)
_cell_length_b                   24.190(5)
_cell_length_c                   17.139(5)
_cell_measurement_temperature    100(2)
_cell_volume                     2393(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0943
_diffrn_reflns_av_unetI/netI     0.1123
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12422
_diffrn_reflns_point_group_measured_fraction_full 0.891
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.203
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       Block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 1774 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     578
_refine_ls_number_reflns         7872
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0727
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1108P)^2^+1.1733P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1871
_refine_ls_wR_factor_ref         0.2208
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.781
_reflns_Friedel_fraction_max     0.774
_reflns_number_gt                5893
_reflns_number_total             7872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5025794_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
Adding full bibliography for 1518012--1518013.cif.

2019-02-11
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C56 H50 N6 O6 S2'
_cod_original_formula_weight         967.14
_cod_original_formula_units_Z            2
_cod_database_code               1518013
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              67609
_shelx_hkl_checksum              45339
_shelx_fab_checksum              37975