Regioselective synthesis of 3-acylindolizines and benzo- analogues via 1,3-dipolar cycloadditions of N-ylides with maleic anhydride.
Liu, Yun; Zhang, Yan; Shen, Yong-Miao; Hu, Hong-Wen; Xu, Jian-Hua; Organic & biomolecular chemistry 8 (2010) 2449–2456; doi:10.1039/c000277a

data_7153335
_publ_section_title
;
 Regioselective synthesis of 3-acylindolizines and benzo- analogues via
 1,3-dipolar cycloadditions of N-ylides with maleic anhydride.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2449
_journal_page_last               2456
_journal_paper_doi               10.1039/c000277a
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C19 H12 F N O'
_chemical_formula_sum            'C19 H12 F N O'
_chemical_formula_weight         289.29
_chemical_melting_point          393
_chemical_name_systematic        1-(4-Fluorobenzoyl)pyrrolo[1,2-a]quinoline
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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-97
_cell_angle_alpha                103.97(3)
_cell_angle_beta                 105.05(3)
_cell_angle_gamma                102.57(3)
_cell_formula_units_Z            4
_cell_length_a                   7.8880(16)
_cell_length_b                   13.530(3)
_cell_length_c                   14.876(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1419.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0906
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5569
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.49
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method 'petroleum ether-ethyl acetate'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.0692
_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^)+(0.0600P)^2^+1.7500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.2004
_reflns_number_gt                2829
_reflns_number_total             5162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c000277a.txt
_cod_data_source_block           l
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '393K' was changed to '393' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1419.7(5)
_cod_database_code               7153335