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_4032983
_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         'C16 H12 N2'
_chemical_formula_sum            'C16 H12 N2'
_chemical_formula_weight         232.28
_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     direct
_audit_creation_date             2016-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.656(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.456(2)
_cell_length_b                   9.1464(9)
_cell_length_c                   7.7710(11)
_cell_measurement_reflns_used    1157
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2060
_cell_measurement_theta_min      3.46
_cell_volume                     1229.7(3)
_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_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.852
_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      7.00  79.00   1.00    7.50    --   16.81  37.00  60.00   72
  2  \w     51.00  82.00   1.00    7.50    --   16.81  19.00 -90.00   31
  3  \w     -2.00  85.00   1.00    7.50    --   16.81  57.00 -30.00   87
  4  \w     -2.00  23.00   1.00    7.50    --  -17.43 -99.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0377427000
_diffrn_orient_matrix_UB_12      0.0056384000
_diffrn_orient_matrix_UB_13      0.0235765000
_diffrn_orient_matrix_UB_21      0.0159489000
_diffrn_orient_matrix_UB_22      0.0107529000
_diffrn_orient_matrix_UB_23      0.0879638000
_diffrn_orient_matrix_UB_31      0.0005094000
_diffrn_orient_matrix_UB_32      0.0765946000
_diffrn_orient_matrix_UB_33      -0.0140987000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5416
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.041
_diffrn_reflns_theta_min         3.241
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_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    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.056
_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     164
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0526P)^2^+0.1146P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1838
_reflns_number_total             2798
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02278_si_002.cif
_cod_data_source_block           exp_1847
_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_cell_volume        1229.6(3)
_cod_original_formula_moiety     '0.8(C16 H12 N2)'
_cod_original_formula_sum        'C12.80 H9.60 N1.60'
_cod_original_formula_units_Z    5
_cod_original_formula_weight     185.82
_cod_database_code               4032983
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H007(0.054) H008(0.057) H009(0.057) H00A(0.064) H00B(0.066)
 H00C(0.088) H00D(0.088) H00E(0.088) H00F(0.072) H00G(0.073) H00H(0.073)
 H00I(0.08)
 Fixed X: H007(0.3175) H008(0.0952) H009(0.2464) H00A(0.4393) H00B(0.4571)
 H00C(0.138) H00D(0.19) H00E(0.1399) H00F(0.1496) H00G(0.5104) H00H(-0.0015)
 H00I(0.0256)
 Fixed Y: H007(0.9273) H008(0.6821) H009(0.9505) H00A(0.9305) H00B(0.4977)
 H00C(0.5233) H00D(0.3838) H00E(0.4076) H00F(1.1203) H00G(0.7151) H00H(0.8507)
 H00I(1.0703)
 Fixed Z: H007(0.6456) H008(0.6031) H009(0.8775) H00A(0.5753) H00B(0.6373)
 H00C(0.8806) H00D(0.9132) H00E(0.7325) H00F(0.8851) H00G(0.5726) H00H(0.6181)
 H00I(0.7572)
;
_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 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.895