Ketones as electrophiles in two component Baylis-Hillman reaction: a facile one-pot synthesis of substituted indolizines.
Basavaiah, Deevi; Veeraraghavaiah, Gorre; Badsara, Satpal Singh; Organic & biomolecular chemistry 12 (2014) 1551–1555; doi:10.1039/c3ob42064g

data_7153585
_publ_section_title
;
 Ketones as electrophiles in two component Baylis-Hillman reaction: a
 facile one-pot synthesis of substituted indolizines.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1551
_journal_page_last               1555
_journal_paper_doi               10.1039/c3ob42064g
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_chemical_melting_point          126.5(5)
_chemical_name_systematic
; 
 8-Acetyl-1-aza-2-Methoxy-7-methylbicyclo[4.3.0]nona-2,4,6,8-tetraene 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.886(4)
_cell_length_b                   8.048(2)
_cell_length_c                   17.590(4)
_cell_measurement_reflns_used    3213
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.37
_cell_measurement_theta_min      2.32
_cell_volume                     2107.3(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20200
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.170
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0635
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+0.6009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1466
_reflns_number_gt                1687
_reflns_number_total             2070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42064g.txt
_cod_data_source_block           3f
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '126-127' was changed to '126.5(5)' -
the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        2107.2(9)
_cod_original_sg_symbol_H-M      'Pbca '
_cod_database_code               7153585