Synthesis of chiral (tetrazolyl)methyl-containing acrylates via silicon-induced organocatalytic kinetic resolution of Morita-Baylis-Hillman fluorides.
Nishimine, Takayuki; Taira, Hiromi; Mori, Satoru; Matsubara, Okiya; Tokunaga, Etsuko; Akiyama, Hidehiko; Soloshonok, Vadim A.; Shibata, Norio; Chemical communications (Cambridge, England) 53 (2017) 1128–1131; doi:10.1039/c6cc08830a

data_7119192
_publ_section_title
;
 Synthesis of chiral (tetrazolyl)methyl-containing acrylates via
 silicon-induced organocatalytic kinetic resolution of
 Morita-Baylis-Hillman fluorides.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1128
_journal_page_last               1131
_journal_paper_doi               10.1039/c6cc08830a
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 Br N4 O2'
_chemical_formula_sum            'C19 H17 Br N4 O2'
_chemical_formula_weight         413.27
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-08-30 deposited with the CCDC.
2016-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.4218(12)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   22.9684(11)
_cell_length_b                   6.4549(3)
_cell_length_c                   12.7545(6)
_cell_measurement_reflns_used    6781
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      3.29
_cell_volume                     1822.88(15)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9001
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.283
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             840.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.590
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1697 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.008(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3971
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0272P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                2600
_reflns_number_total             3971
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6cc08830a2.cif
_cod_data_source_block           20160706matsubara-1
_cod_depositor_comments          'Adding full bibliography for 7119192.cif.'
_cod_original_cell_volume        1822.88(14)
_cod_database_code               7119192