Pd(II)-catalyzed annulation of terminal alkynes with 2-pyridinyl-substituted p-quinone methides: Direct access to indolizines
Ahmad, Feroz; Ranga, Pavit K.; Pankhade, Yogesh A.; Fatma, Shaheen; Gouda, Ashrumochan; Vijaya Anand, Ramasamy; Chemical Communications  (2022) –; doi:10.1039/D2CC04395E

data_7130949
_publ_section_title
;
 Pd(II)-catalyzed annulation of terminal alkynes with
 2-pyridinyl-substituted p-quinone methides: Direct access to indolizines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04395E
_journal_year                    2022
_chemical_formula_moiety         'C29 H33 N O2'
_chemical_formula_sum            'C29 H33 N O2'
_chemical_formula_weight         427.56
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-12-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-01-03 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.843(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5189(4)
_cell_length_b                   10.2586(4)
_cell_length_c                   18.1361(7)
_cell_measurement_reflns_used    3700
_cell_measurement_temperature    150.02(10)
_cell_measurement_theta_max      32.3500
_cell_measurement_theta_min      2.6030
_cell_volume                     2307.37(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXH-1997  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_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    -69.00 118.20   0.30   10.00    --   29.89  54.00   0.00  624
  2  \w    -69.00  36.00   0.30   10.00    --   29.89  54.00  60.00  350
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0261118000
_diffrn_orient_matrix_UB_12      -0.0609778000
_diffrn_orient_matrix_UB_13      -0.0070947000
_diffrn_orient_matrix_UB_21      -0.0468672000
_diffrn_orient_matrix_UB_22      0.0324629000
_diffrn_orient_matrix_UB_23      -0.0174806000
_diffrn_orient_matrix_UB_31      0.0199640000
_diffrn_orient_matrix_UB_32      -0.0038564000
_diffrn_orient_matrix_UB_33      -0.0346247000
_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  0.0522
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16666
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.79
_diffrn_reflns_theta_min         2.58
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         7963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0708
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1150P)^2^+0.2381P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.2251
_reflns_number_gt                5527
_reflns_number_total             7963
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc04395e2.cif
_cod_data_source_block           xii-fz-23
_cod_database_code               7130949
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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:
 C8(H8), C6(H6), C21(H21), C20(H20), C24(H24), C27(H27), C25(H25), C28(H28),
 C19(H19), C18(H18), C17(H17)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C2(H2A,H2B,
 H2C), C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C29(H29A,H29B,H29C)
;
_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 2.149
_oxdiff_exptl_absorpt_empirical_full_min 0.625