Synthesis of fused tricyclic indolizines by intramolecular silver-mediated double cyclization of 2-(pyridin-2-yl)acetic acid propargyl esters
Zhao, Hai-Yuan; Wang, Ying-chun; Cao, Xiao-Lin; Pang, Qiu-Fang; Wang, Heng-shan; Pan, Ying-ming; RSC Adv. 7 (2017) 24011–; doi:10.1039/C7RA00892A

data_7228198
_publ_section_title
;
 Synthesis of fused tricyclic indolizines by intramolecular
 silver-mediated double cyclization of 2-(pyridin-2-yl)acetic acid
 propargyl esters
;
_journal_issue                   39
_journal_name_full               'RSC Adv.'
_journal_page_first              24011
_journal_paper_doi               10.1039/C7RA00892A
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C12 H11 N O2'
_chemical_formula_sum            'C11 H10 N O'
_chemical_formula_weight         172.20
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-11-23
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2016-08-30 deposited with the CCDC.
2017-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.480(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0248(7)
_cell_length_b                   12.1750(12)
_cell_length_c                   10.5501(12)
_cell_measurement_reflns_used    2459
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2060
_cell_measurement_theta_min      3.9110
_cell_volume                     1013.57(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9128
_diffrn_measurement_details
;
  1 omega  -44.00   54.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -18.4732   38.0000   30.0000 98

  2 omega  -39.00   50.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -18.4732   57.0000  120.0000 89

  3 omega  -20.00   61.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.4888  -99.0000  -60.0000 81

  4 omega   35.00   95.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       19.4888  178.0000    0.0000 60

  5 omega  -89.00  -64.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -18.4732  -77.0000    0.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0312381000
_diffrn_orient_matrix_UB_12      -0.0211268000
_diffrn_orient_matrix_UB_13      0.0624899000
_diffrn_orient_matrix_UB_21      0.0343035000
_diffrn_orient_matrix_UB_22      0.0523158000
_diffrn_orient_matrix_UB_23      0.0196458000
_diffrn_orient_matrix_UB_31      -0.0769346000
_diffrn_orient_matrix_UB_32      0.0146721000
_diffrn_orient_matrix_UB_33      0.0195765000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6574
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2061
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.1519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                1735
_reflns_number_total             2061
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra00892a2.cif
_cod_data_source_block           20151123-pym-zhy-2242
_cod_database_code               7228198
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32