Cationic palladium(ii)-catalyzed synthesis of substituted pyridines from α,β-unsaturated oxime ethers
Yamada, Takahiro; Hashimoto, Yoshimitsu; Tanaka, Kosaku; Morita, Nobuyoshi; Tamura, Osamu; RSC Advances 12 (2022) 21548–21557; doi:10.1039/D2RA03875G

data_7245268
_publ_section_title
;
 Cationic palladium(ii)-catalyzed synthesis of substituted pyridines from
 \a,\b-unsaturated oxime ethers
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              21548
_journal_page_last               21557
_journal_paper_doi               10.1039/D2RA03875G
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C15 H19 N O'
_chemical_formula_sum            'C15 H19 N O'
_chemical_formula_weight         229.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-16
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-04-16 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.3602(3)
_cell_length_b                   6.9650(3)
_cell_length_c                   50.466(2)
_cell_measurement_reflns_used    6223
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9840
_cell_measurement_theta_min      6.2430
_cell_volume                     2587.08(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.63a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.948
_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     78.00 111.00   0.50    0.05    --   48.95 125.00 150.00   66
  2  \w     93.00 173.00   0.50    0.12    --  107.74  11.00  56.00  160
  3  \w    -12.00  25.00   0.50    0.05    --   48.95 -19.00 -30.00   74
  4  \w     -1.00  25.00   0.50    0.05    --   48.95 -19.00 -90.00   52
  5  \w     76.00 101.00   0.50    0.05    --   48.95 125.00-180.00   50
  6  \w     -8.00  25.00   0.50    0.05    --   48.95 -19.00-180.00   66
  7  \w     45.00  70.00   0.50    0.12    --  107.74 -99.00 -30.00   50
  8  \w     70.00 108.00   0.50    0.12    --  107.74-117.00 122.00   76
  9  \w     36.00  66.00   0.50    0.12    --  107.74-117.00 122.00   60
 10  \w     73.00  98.00   0.50    0.12    --  107.74 -99.00 -30.00   50
 11  \w    -56.00 -30.00   0.50    0.12    --  -97.00  57.00-120.00   52
 12  \w    -95.00 -64.00   0.50    0.05    --  -48.95 140.00 -74.00   62
 13  \w    -65.00 -38.00   0.50    0.12    --  -97.00  57.00 150.00   54
 14  \w   -158.00 -76.00   0.50    0.12    --  -97.00-140.00-134.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-Custom'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0263528000
_diffrn_orient_matrix_UB_12      -0.0542773000
_diffrn_orient_matrix_UB_13      -0.0293474000
_diffrn_orient_matrix_UB_21      -0.0155455000
_diffrn_orient_matrix_UB_22      -0.2140787000
_diffrn_orient_matrix_UB_23      0.0072617000
_diffrn_orient_matrix_UB_31      -0.2071631000
_diffrn_orient_matrix_UB_32      0.0090599000
_diffrn_orient_matrix_UB_33      -0.0042597000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            8847
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.167
_diffrn_reflns_theta_min         5.259
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.63a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       prism
_exptl_crystal_F_000             1001
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+1.3792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2349
_reflns_number_total             2574
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra03875g2.cif
_cod_data_source_block           exp_224
_cod_depositor_comments
;

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C11 H10 N O'
_cod_original_formula_weight         172.20
_cod_original_formula_moiety         '0.73(C15 H19 N O)'
_cod_original_formula_units_Z            11
_cod_original_cell_volume        2587.09(19)
_cod_database_code               7245268
_shelx_shelxl_version_number     2018/3
_diffrn_oxdiff_digest_frames
;
01935ab971be8505fff41e794c66a12ef30006606b7
;
_diffrn_oxdiff_digest_hkl
;
01c99b92f9f75763add5da5c9567723e6b55da
;
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00B(H00D,H00E), C00E(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C003(H003), C006(H006), C009(H009), C00A(H00C), C00C(H00F), C00D(H00G)
2.d Idealised Me refined as rotating group:
 C00G(H00K,H00L,H00M), C00H(H00N,H00O,H00P)
;
_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 1.513
_oxdiff_exptl_absorpt_empirical_full_min 0.796