Modulating the Reactivity of Heterocyclic Ketene Aminals in MCR: Selective Construction of Tetrahydrobenzo[b]imidazo[3,2,1-ij][1,8]naphthyridines
Li-Rong Wen; Chao Liu; Ming Li; Li-Juan Wang; Journal of Organic Chemistry 75 (2010) 7605–7614; doi:10.1021/jo101454q

data_4025802
_publ_section_title
;
 Modulating the Reactivity of Heterocyclic Ketene Aminals in MCR:
 Selective Construction of
 Tetrahydrobenzo[b]imidazo[3,2,1-ij][1,8]naphthyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7605
_journal_page_last               7614
_journal_paper_doi               10.1021/jo101454q
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C24 H21 Cl N2 O3'
_chemical_formula_sum            'C24 H21 Cl N2 O3'
_chemical_formula_weight         420.88
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.237(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.082(7)
_cell_length_b                   9.455(4)
_cell_length_c                   28.430(13)
_cell_measurement_reflns_used    19976
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      1.44
_cell_volume                     4030(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0957
_diffrn_reflns_av_sigmaI/netI    0.1221
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            19976
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.9721
_exptl_absorpt_correction_T_min  0.9473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SHELXTL  Ver. 5.10  DOS/WIN95/NT'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         7125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.0632
_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^)+(0.0616P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1757
_reflns_number_gt                3121
_reflns_number_total             7125
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101454q_si_001.cif
_cod_data_source_block           6c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025802