α-Regioselective Asymmetric [3 + 2] Annulations of Morita-Baylis-Hillman Carbonates with Cyclic 1-Azadienes and Mechanism Elucidation.
Wang, Kai-Kai; Jin, Tian; Huang, Xin; Ouyang, Qin; Du, Wei; Chen, Ying-Chun; Organic letters 18 (2016) 872–875; doi:10.1021/acs.orglett.6b00189

data_1542641
_publ_section_title
;
 \a-Regioselective Asymmetric [3 + 2] Annulations of Morita-Baylis-Hillman
 Carbonates with Cyclic 1-Azadienes and Mechanism Elucidation.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              872
_journal_page_last               875
_journal_paper_doi               10.1021/acs.orglett.6b00189
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C26 H21 N O4 S'
_chemical_formula_sum            'C26 H21 N O4 S'
_chemical_formula_weight         443.50
_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     direct
_audit_creation_date             2015-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.404(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5173(4)
_cell_length_b                   9.24556(19)
_cell_length_c                   15.6647(5)
_cell_measurement_reflns_used    4785
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.1600
_cell_measurement_theta_min      5.5270
_cell_volume                     2247.30(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   23.00   90.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000   30.0000 67

  2 omega    1.00   75.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -99.0000 -120.0000 74

  3 omega   19.00  103.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000 -120.0000 84

  4 omega   23.00   90.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.1671 -125.0000  -30.0000 67

  5 omega   19.00  103.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   57.0000 -180.0000 84

  6 omega  -31.00   53.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000    0.0000 84

  7 omega   38.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

  8 omega   38.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

  9 omega   40.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 10 omega   91.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 11 omega  100.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 78

 12 omega   38.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 13 omega   39.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

 14 omega   38.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

 15 omega   38.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 16 omega   38.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 17 omega   87.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 91

 18 omega  -31.00   10.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.1671  -57.0000   90.0000 41

 19 omega   19.00  104.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.1671   52.0000   24.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0539356000
_diffrn_orient_matrix_UB_12      -0.0707421000
_diffrn_orient_matrix_UB_13      -0.0708859000
_diffrn_orient_matrix_UB_21      -0.0549429000
_diffrn_orient_matrix_UB_22      0.0779200000
_diffrn_orient_matrix_UB_23      -0.0680491000
_diffrn_orient_matrix_UB_31      0.0626509000
_diffrn_orient_matrix_UB_32      0.1293584000
_diffrn_orient_matrix_UB_33      0.0022864000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12237
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         5.556
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.550
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description
;
;
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0696
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1165P)^2^+0.9688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2006
_refine_ls_wR_factor_ref         0.2090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3439
_reflns_number_total             4006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00189_si_003.cif
_cod_data_source_block           7
_cod_database_code               1542641
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Rigid bond restraints
 C00P, C00R
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Ternary CH refined with riding coordinates:
 C005(H005), C007(H007), C008(H008)
3.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V)
3.c Idealised Me refined as rotating group:
 C00W(H00A,H00B,H00C)
;
_shelx_res_checksum              51842
_shelx_hkl_checksum              37392
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-17
_olex2_submission_special_instructions 'No special instructions were received'