Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis
Albota, Florin; Caira, Mino R.; Draghici, Constantin; Dumitrascu, Florea; Dumitrescu, Denisa E.; Beilstein Journal of Organic Chemistry 12 (2016) 2503–; doi:10.3762/bjoc.12.245

data_4032071
_publ_section_title
;
 Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin
 indolizine synthesis
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              2503
_journal_paper_doi               10.3762/bjoc.12.245
_journal_volume                  12
_journal_year                    2016
_chemical_formula_moiety         'C23 H21 N3 O5'
_chemical_formula_sum            'C23 H21 N3 O5'
_chemical_formula_weight         419.43
_chemical_melting_point          481.0(10)
_chemical_name_common            none
_chemical_name_systematic
'Ethyl 8-ethyl-5-methyl-3-[(3-phenylsydnon-4-yl)-oxomethyl]-indolizine-1-carboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                93.4800(10)
_cell_angle_beta                 95.8860(10)
_cell_angle_gamma                109.3060(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9685(5)
_cell_length_b                   10.6487(7)
_cell_length_c                   11.0785(7)
_cell_measurement_reflns_used    5162
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.59
_cell_volume                     988.21(11)
_computing_cell_refinement       'SAINT, V.7.60a, Bruker AXS Inc, 2006'
_computing_data_collection       'SAINT, V.7.60a, Bruker AXS Inc, 2006'
_computing_data_reduction        'SAINT, V.7.60a, Bruker AXS Inc, 2006'
_computing_molecular_graphics    'POV-Ray for Windows, 2003'
_computing_publication_material  'PLATON (A.L. Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex II diffractometer'
_diffrn_measurement_method       'phi- and omega-scans of 0.5 deg.'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16785
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.150
_diffrn_reflns_theta_min         1.857
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0452P)^2^+0.2322P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3586
_reflns_number_total             4376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-12-245-S3.cif
_cod_data_source_block           C:\COMPAQ1\DUMI2016\FA119\FA119
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '480-482 K' was changed to
'481.0(10)' - the average value was taken and precision was
estimated.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               4032071
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.980
_shelx_res_checksum              58700
_shelx_hkl_checksum              63039