An asymmetric and theoretical approach to the Morita-Baylis-Hillman reaction using vinyl-1,2,4-oxadiazoles as nucleophiles.
Chagas, Thaynan A. B.; Piscelli, Bruno A.; Santos, Hugo; Lima, Sâmia R; Cormanich, Rodrigo A.; Fernandes, Fábio S; Coelho, Fernando; Organic & biomolecular chemistry 23 (2025) 5872–5881; doi:10.1039/d5ob00540j

data_7160564
_publ_section_title
;
 An asymmetric and theoretical approach to the Morita-Baylis-Hillman
 reaction using vinyl-1,2,4-oxadiazoles as nucleophiles.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5872
_journal_page_last               5881
_journal_paper_doi               10.1039/d5ob00540j
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H16 N4 O5'
_chemical_formula_structural     C20H16N4O5
_chemical_formula_sum            'C20 H16 N4 O5'
_chemical_formula_weight         392.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-10-18 deposited with the CCDC.	2025-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.9550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6389(4)
_cell_length_b                   14.5769(4)
_cell_length_c                   17.9618(4)
_cell_measurement_reflns_used    9628
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      71.82
_cell_measurement_theta_min      2.50
_cell_volume                     3775.16(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3 (2015)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
'Diamond (H. Putz & K. Brandenburg, 2006, v. 4.6.4)'
_computing_publication_material
'SHELXL-2014/7 (Sheldrick, 2015) and WINGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_diffrn_ambient_temperature      301(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'G\"obbel mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            234530
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.462
_diffrn_reflns_theta_min         2.497
_diffrn_source                   'muS microsource'
_diffrn_source_type              Incoatec
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 6229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1078
_refine_ls_number_reflns         14628
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0634P)^2^+0.4512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1001
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                13826
_reflns_number_total             14628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00540j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7160564.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7160564
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.779
_shelx_estimated_absorpt_t_max   0.864
_shelx_res_checksum              13259