Synthesis of Spirocyclic Oxindole Dihydrothiophenes by DBU-Catalyzed [3 + 2] Annulation of Morita-Baylis-Hillman Carbonates with Isothiocyanates.
Zhao, Yuan-Yuan; Zhao, Shuai; Xie, Ji-Kang; Hu, Xiu-Qin; Xu, Peng-Fei; The Journal of organic chemistry 81 (2016) 10532–10537; doi:10.1021/acs.joc.6b01315

data_4037033
_publ_section_title
;
 Synthesis of Spirocyclic Oxindole Dihydrothiophenes by DBU-Catalyzed [3 +
 2] Annulation of Morita-Baylis-Hillman Carbonates with Isothiocyanates.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10532
_journal_page_last               10537
_journal_paper_doi               10.1021/acs.joc.6b01315
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C21 H17 Br N2 O3 S'
_chemical_formula_sum            'C21 H17 Br N2 O3 S'
_chemical_formula_weight         457.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-05-29
_audit_creation_method
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Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
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_cell_length_a                   10.5994(11)
_cell_length_b                   11.0901(13)
_cell_length_c                   18.718(2)
_cell_measurement_reflns_used    1120
_cell_measurement_temperature    293.64(10)
_cell_measurement_theta_max      19.5060
_cell_measurement_theta_min      3.8280
_cell_volume                     2088.8(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.64(10)
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -52.00  -13.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479   97.0000  122.0000 26

  2 omega    7.00   91.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   38.0000   30.0000 56

  3 omega    8.00   41.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000 -120.0000 22

  4 omega  -18.00   22.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -97.0000   14.0000 27

  5 omega  -20.00   62.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000 -150.0000 55

  6 omega  -32.00   82.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854    0.0000 -180.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      0.0259605000
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_diffrn_orient_matrix_UB_13      -0.0131019000
_diffrn_orient_matrix_UB_21      0.0156093000
_diffrn_orient_matrix_UB_22      0.0323477000
_diffrn_orient_matrix_UB_23      -0.0334796000
_diffrn_orient_matrix_UB_31      0.0627511000
_diffrn_orient_matrix_UB_32      -0.0041872000
_diffrn_orient_matrix_UB_33      0.0133108000
_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.2008
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
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_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14397
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.30
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.091
_exptl_absorpt_correction_T_max  1.00000
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.362
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_refine_ls_number_reflns         8188
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0130P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
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_reflns_number_gt                2770
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_reflns_odcompleteness_completeness 99.73
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C12(H12), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C23(H23), C24(H24), C26(H26), C32(H32), C39(H39), C40(H40), C41(H41),
  C42(H42), C43(H43)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C35(H35A,H35B,H35C), C37(H37A,H37B,
 H37C)
;
_olex2_date_sample_data_collection 2015-05-29
_olex2_submission_special_instructions 'No special instructions were received'