Synthesis of Indolizines via Palladium Catalyzed Annulation of Propargyl Carbonates and 2-(Pyridin-2-yl)acetonitrile Derivatives.
Wu, Ting; Chen, Min; Yang, Yuzhu; The Journal of organic chemistry 82 (2017) 11304–11309; doi:10.1021/acs.joc.7b02278

data_4032984
_publ_section_title
;
 Synthesis of Indolizines via Palladium Catalyzed Annulation of Propargyl
 Carbonates and 2-(Pyridin-2-yl)acetonitrile Derivatives.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11304
_journal_page_last               11309
_journal_paper_doi               10.1021/acs.joc.7b02278
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.36
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.173(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9190(9)
_cell_length_b                   10.0507(9)
_cell_length_c                   16.6196(18)
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    295
_cell_measurement_theta_max      25.4110
_cell_measurement_theta_min      3.0410
_cell_volume                     1643.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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    -21.00  37.00   1.00    6.50    --   16.81 -37.00 -90.00   58
  2  \w    -16.00  57.00   1.00    6.50    --   16.81 -99.00-180.00   73
  3  \w    -53.00  83.00   1.00    6.50    --   16.81   0.00 -30.00  136
  4  \w    -21.00   6.00   1.00    6.50    --  -17.43 -99.00  60.00   27
  5  \w    -12.00  25.00   1.00    6.50    --   16.81  77.00 -60.00   37
  6  \w    -84.00 -55.00   1.00    6.50    --  -17.43 169.00 -63.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0451760000
_diffrn_orient_matrix_UB_12      -0.0525511000
_diffrn_orient_matrix_UB_13      0.0131781000
_diffrn_orient_matrix_UB_21      0.0149428000
_diffrn_orient_matrix_UB_22      -0.0087691000
_diffrn_orient_matrix_UB_23      -0.0403166000
_diffrn_orient_matrix_UB_31      0.0541083000
_diffrn_orient_matrix_UB_32      0.0462531000
_diffrn_orient_matrix_UB_33      0.0072912000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11702
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_min         2.897
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0531P)^2^+0.1387P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2363
_reflns_number_total             3575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02278_si_003.cif
_cod_data_source_block           exp_4018
_cod_depositor_comments
;
Adding full bibliography for 4032983--4032984.cif.

2020-08-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.5(C22 H16 N2)'
_cod_original_formula_sum        'C11 H8 N'
_cod_original_formula_units_Z    8
_cod_original_formula_weight     154.18
_cod_database_code               4032984
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C11(H11), C4(H4), C17(H17), C13(H13), C18(H18), C15(H15),
 C14(H14), C12(H12), C3(H3), C6(H6), C2(H2), C1(H1)
;
_shelx_res_checksum              64713
_shelx_hkl_checksum              75331
_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 2.148
_oxdiff_exptl_absorpt_empirical_full_min 0.624