A sequential reaction of picolinamide with benzaldehydes promoted by Pd(TFA)<sub>2</sub>: rapid access to 4,5-disubstituted 2-(pyridin-2-yl)oxazoles in <i>n</i>-octane.
Nakayama, Taku; Fujiki, Sayaka; Enda, Tomokatsu; Kikkawa, Shoko; Hikawa, Hidemasa; Azumaya, Isao; Organic & biomolecular chemistry 22 (2024) 759–766; doi:10.1039/d3ob01815f

data_7159730
_publ_section_title
;
 A sequential reaction of picolinamide with benzaldehydes promoted by
 Pd(TFA)<sub>2</sub>: rapid access to 4,5-disubstituted
 2-(pyridin-2-yl)oxazoles in <i>n</i>-octane.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              759
_journal_page_last               766
_journal_paper_doi               10.1039/d3ob01815f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C32 H22 N2 O'
_chemical_formula_sum            'C32 H22 N2 O'
_chemical_formula_weight         450.51
_space_group_crystal_system      tetragonal
_space_group_IT_number           114
_space_group_name_Hall           'P -4 2n'
_space_group_name_H-M_alt        'P -4 21 c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-06 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.6044(8)
_cell_length_b                   23.6044(8)
_cell_length_c                   8.2487(5)
_cell_measurement_reflns_used    6039
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      21.1960
_cell_measurement_theta_min      2.4420
_cell_volume                     4595.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -87.00  75.00   0.50    5.00    --  -15.00  55.00-180.00  324
  2  \w    -84.50  70.50   0.50    5.00    --  -15.00  27.00  90.00  310
  3  \w    -70.00 -43.00   0.50    5.00    --  -15.00  55.00   0.00   54
  4  \w     -8.00  17.50   0.50    5.00    --  -15.00  27.00 -90.00   51
  5  \w   -103.50 -78.50   0.50    5.00    --  -15.00   0.00 -90.00   50
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0106476000
_diffrn_orient_matrix_UB_12      0.0120420000
_diffrn_orient_matrix_UB_13      0.0726631000
_diffrn_orient_matrix_UB_21      0.0113123000
_diffrn_orient_matrix_UB_22      -0.0266673000
_diffrn_orient_matrix_UB_23      0.0226476000
_diffrn_orient_matrix_UB_31      0.0257071000
_diffrn_orient_matrix_UB_32      0.0068106000
_diffrn_orient_matrix_UB_33      -0.0401360000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1174
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            37804
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.616
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       prism
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1223 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5281
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0589
_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^)+(0.0501P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3688
_reflns_number_total             5281
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01815f2.cif
_cod_data_source_block           sfu03
_cod_depositor_comments          'Adding full bibliography for 7159730.cif.'
_cod_database_code               7159730
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C7, N11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C26(H26), C25(H25), C17(H17), C14(H14), C31(H31), C29(H29), C19(H19),
 C28(H28), C16(H16), C13(H13), C35(H35), C32(H32), C34(H34), C20(H20), C3(H3),
 C23(H23), C6(H6), C33(H33), C5(H5), C4(H4), C22(H22), C21(H21)
;
_shelx_res_checksum              1785
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.992
_oxdiff_exptl_absorpt_empirical_full_min 0.706