An efficient synthesis of pyrrolo[2,3,4-kl]acridin-1-one derivatives catalyzed by L-proline.
Wang, Huiyuan; Li, Lili; Lin, Wei; Xu, Pan; Huang, Zhibin; Shi, Daqing; Organic letters 14 (2012) 4598–4601; doi:10.1021/ol302058g

data_1508628
_publ_section_title
;
 An efficient synthesis of pyrrolo[2,3,4-kl]acridin-1-one derivatives
 catalyzed by L-proline.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4598
_journal_page_last               4601
_journal_paper_doi               10.1021/ol302058g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C20 H10 Cl F N2 O'
_chemical_formula_sum            'C20 H10 Cl F N2 O'
_chemical_formula_weight         348.75
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                94.429(6)
_cell_angle_beta                 100.123(7)
_cell_angle_gamma                114.107(7)
_cell_formula_units_Z            2
_cell_length_a                   8.3506(6)
_cell_length_b                   8.5287(6)
_cell_length_c                   12.1084(10)
_cell_measurement_reflns_used    1888
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4660
_cell_measurement_theta_min      3.2605
_cell_volume                     764.16(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4692
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\w 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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4806
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0428P)^2^+0.2347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                2145
_reflns_number_total             2684
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302058g_si_002.cif
_cod_data_source_block           g120713c
_cod_original_cell_volume        764.16(10)
_cod_database_code               1508628