Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids.
Morrill, Louis C.; Smith, Samuel M.; Slawin, Alexandra M. Z.; Smith, Andrew D.; The Journal of organic chemistry 79 (2014) 1640–1655; doi:10.1021/jo402591v

data_4028986
_publ_section_title
;
 Isothiourea-mediated asymmetric functionalization of 3-alkenoic acids.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1640
_journal_page_last               1655
_journal_paper_doi               10.1021/jo402591v
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H18 Br N O3 S'
_chemical_formula_sum            'C19 H18 Br N O3 S'
_chemical_formula_weight         420.32
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_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   5.8546(15)
_cell_length_b                   12.369(3)
_cell_length_c                   25.480(6)
_cell_measurement_reflns_used    6099
_cell_measurement_temperature    93
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.83
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_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_collection
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
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_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
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_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11753
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
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_diffrn_reflns_theta_max         25.315
_diffrn_reflns_theta_min         1.830
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856.00
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.030
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_refine_ls_abs_structure_details
'Parsons and Flack (2004), Acta Cryst. A60, s61.  880 quotients'
_refine_ls_abs_structure_Flack   0.033(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0309P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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