Divergent synthesis of two types of indolizines from pyridine-2-acetonitrile, (hetero)arylglyoxal, and TMSCN.
Nam, Seonghyeon; Lee, Sunhee; Kim, Woojin; Kim, Ikyon; Organic & biomolecular chemistry 21 (2023) 3881–3895; doi:10.1039/d3ob00471f

data_7159305
_publ_section_title
;
 Divergent synthesis of two types of indolizines from
 pyridine-2-acetonitrile, (hetero)arylglyoxal, and TMSCN.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3881
_journal_page_last               3895
_journal_paper_doi               10.1039/d3ob00471f
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H13 N3 O'
_chemical_formula_sum            'C16 H13 N3 O'
_chemical_formula_weight         263.29
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2022-12-28
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_audit_update_record
;
2023-03-03 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.158(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7205(14)
_cell_length_b                   13.737(3)
_cell_length_c                   11.3839(19)
_cell_measurement_reflns_used    1055
_cell_measurement_temperature    293.9(7)
_cell_measurement_theta_max      24.1660
_cell_measurement_theta_min      2.7820
_cell_volume                     1342.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.9(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4525
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.816
_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    -19.00  29.00   4.00  978.54    --  -11.04 -99.00  90.00   12
  2  \w    -62.00  78.00   4.00  978.54    --   11.83   0.00-150.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0290118000
_diffrn_orient_matrix_UB_12      0.0270877000
_diffrn_orient_matrix_UB_13      -0.0521635000
_diffrn_orient_matrix_UB_21      0.0140843000
_diffrn_orient_matrix_UB_22      0.0438710000
_diffrn_orient_matrix_UB_23      0.0330479000
_diffrn_orient_matrix_UB_31      0.0761101000
_diffrn_orient_matrix_UB_32      0.0022103000
_diffrn_orient_matrix_UB_33      -0.0139240000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.1328
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6480
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.531
_diffrn_reflns_theta_min         2.346
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
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    1.303
_exptl_crystal_description       irregular
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1816
_refine_ls_R_factor_gt           0.0778
_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^)+(0.0860P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1788
_refine_ls_wR_factor_ref         0.2429
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1324
_reflns_number_total             3057
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00471f2.cif
_cod_data_source_block           exp_1871
_cod_depositor_comments
'Adding full bibliography for 7159305--7159306.cif.'
_cod_original_cell_volume        1342.4(4)
_cod_database_code               7159305
_chemical_oxdiff_formula         C17H11N3O
_diffrn_oxdiff_ac3_digest_frames
;
01f46a7e864eb5ea0c31b6dbf2790275c000046f3fd
;
_diffrn_oxdiff_ac3_digest_hkl
;
01a8115707e11a60b5e3a6165ba922371feb3b
;
_reflns_odcompleteness_completeness 97.95
_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 N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N003(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00C(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J)
2.c Idealised Me refined as rotating group:
 C00K(H00K,H00L,H00M)
;
_shelx_res_checksum              72348
_shelx_shelxl_version_number     2018/3
_olex2_date_sample_data_collection 2022-12-26
_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 3.393
_oxdiff_exptl_absorpt_empirical_full_min 0.505