Vinyl-1,2,4-oxadiazoles Behave as Nucleophilic Partners in Morita-Baylis-Hillman Reactions.
Fernandes, Fábio S; Rodrigues, Jr, Manoel T; Zeoly, Lucas A.; Conti, Caroline; Angolini, Célio F F; Eberlin, Marcos Nogueira; Coelho, Fernando; The Journal of organic chemistry 83 (2018) 15118–15127; doi:10.1021/acs.joc.8b02402

data_4034727
_publ_section_title
;
 Vinyl-1,2,4-oxadiazoles Behave as Nucleophilic Partners in
 Morita-Baylis-Hillman Reactions.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15118
_journal_page_last               15127
_journal_paper_doi               10.1021/acs.joc.8b02402
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C16 H13 N3 O2'
_chemical_formula_sum            'C16 H13 N3 O2'
_chemical_formula_weight         279.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.6150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.3985(9)
_cell_length_b                   5.7117(2)
_cell_length_c                   13.6214(6)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.290
_cell_measurement_theta_min      2.311
_cell_volume                     1371.66(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.8682
_diffrn_measured_fraction_theta_max 0.8682
_diffrn_measurement_device_type  'BRUKER APEX CCD DETECTOR DIFFRACTOMETER'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38707
_diffrn_reflns_theta_full        29.5717
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         3.89
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0512 before and 0.0459 after correction.
The Ratio of minimum to maximum transmission is 0.9224.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.3524
_exptl_crystal_description       block
_exptl_crystal_F_000             584.2697
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.2573
_refine_diff_density_min         -0.3333
_refine_diff_density_rms         0.0532
_refine_ls_d_res_high            0.7201
_refine_ls_d_res_low             5.2326
_refine_ls_goodness_of_fit_ref   1.0608
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0608
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.4005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1107
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              -25
_reflns_limit_k_max              7
_reflns_limit_k_min              1
_reflns_limit_l_max              18
_reflns_limit_l_min              1
_reflns_number_gt                2688
_reflns_number_total             3334
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b02402_si_001.cif
_cod_data_source_block           ZEOLY_a
_cod_database_code               4034727
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C4(H4), C15(H15), C2(H2a), C1(H1), C5(H5), C3(H3)
2.c Tetrahedral OH refined with riding coordinates:
 O2(H2)
2.d X=CH2 refined with riding coordinates:
 C10(H10a,H10b)
;
_olex2_submission_original_sample_id OXADIAZOLE-3-PIRIDINO
_olex2_submission_special_instructions 'No special instructions were received'