Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita-Baylis-Hillman carbonates
Victor Ceban; Piotr Putaj; Marta Meazza; Mateusz B. Pitak; Simon J. Coles; Jan Vesely; Ramon Rios; Chem.Commun. 50 (2014) 7447–; doi:10.1039/C4CC00728J

data_7114633
_publ_section_title
;
 Synergistic catalysis: highly diastereoselective benzoxazole addition to
 Morita-Baylis-Hillman carbonates
;
_journal_name_full               Chem.Commun.
_journal_page_first              7447
_journal_paper_doi               10.1039/C4CC00728J
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C20 H17 Br N2 O5'
_chemical_formula_sum            'C20 H17 Br N2 O5'
_chemical_formula_weight         445.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                70.132(5)
_cell_angle_beta                 68.095(5)
_cell_angle_gamma                80.935(6)
_cell_formula_units_Z            2
_cell_length_a                   8.9971(4)
_cell_length_b                   10.0949(4)
_cell_length_c                   11.5631(8)
_cell_measurement_reflns_used    11418
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     915.83(9)
_computing_cell_refinement
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)'
_computing_data_collection
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)'
_computing_data_reduction
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support MiTeGen
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12120
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         3.194
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    2.280
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0318P)^2^+0.6407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0684
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3969
_reflns_number_total             4167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc00728j3.cif
_cod_data_source_block           2013ncs0652
_cod_database_code               7114633
_shelx_estimated_absorpt_t_min   0.611
_shelx_estimated_absorpt_t_max   0.914
_shelxl_version_number           2013-4
_shelx_res_checksum              15559