Umpolung coupling of pyridine-2-carboxaldehydes and propargylic carbonates <i>via</i> N-heterocyclic carbene/palladium synergetic catalysis.
Bi, Weiyang; Yang, Yunhui; Ye, Song; Wang, Congyang; Chemical communications (Cambridge, England) 57 (2021) 4452–4455; doi:10.1039/d1cc01311d

data_7128097
_publ_section_title
;
 Umpolung coupling of pyridine-2-carboxaldehydes and propargylic
 carbonates <i>via</i> N-heterocyclic carbene/palladium synergetic
 catalysis.
;
_journal_issue                   36
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4452
_journal_page_last               4455
_journal_paper_doi               10.1039/d1cc01311d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C25 H19 N O'
_chemical_formula_sum            'C25 H19 N O'
_chemical_formula_weight         349.41
_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_Hall           '-P 4bc'
_space_group_name_H-M_alt        'P 42/n :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-06 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.9496(3)
_cell_length_b                   21.9496(3)
_cell_length_c                   7.9389(2)
_cell_measurement_reflns_used    14083
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      29.8170
_cell_measurement_theta_min      2.1000
_cell_volume                     3824.84(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.903
_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 -61.00   0.50    5.00    --  -14.80  45.00  60.00   52
  2  \w    -14.00  74.00   0.50    5.00    --  -14.80  45.00  60.00  176
  3  \w   -103.00  -6.00   0.50    5.00    --  -14.80  45.00  30.00  194
  4  \w     24.00  68.00   0.50    5.00    --  -14.80  45.00  30.00   88
  5  \w     -6.00  74.00   0.50    5.00    --  -14.80  45.00 -19.01  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047342000
_diffrn_orient_matrix_UB_12      -0.0218691000
_diffrn_orient_matrix_UB_13      0.0645108000
_diffrn_orient_matrix_UB_21      0.0319067000
_diffrn_orient_matrix_UB_22      -0.0048397000
_diffrn_orient_matrix_UB_23      0.0054788000
_diffrn_orient_matrix_UB_31      0.0020523000
_diffrn_orient_matrix_UB_32      0.0232725000
_diffrn_orient_matrix_UB_33      0.0616048000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            31950
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.643
_diffrn_reflns_theta_min         1.856
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
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    1.214
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         5346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0560P)^2^+0.7076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1189
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4454
_reflns_number_total             5346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01311d2.cif
_cod_data_source_block           mx8850
_cod_depositor_comments          'Adding full bibliography for 7128097.cif.'
_cod_original_cell_volume        3824.84(14)
_cod_original_sg_symbol_H-M      'P 42/n'
_cod_database_code               7128097
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C18(H18), C19(H19),
 C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              29777
_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 1.112
_oxdiff_exptl_absorpt_empirical_full_min 0.901