Visible Light Photoredox Catalysis: Synthesis of Indazolo[2,3-a]quinolines from 2-(2-Nitrophenyl)-1,2,3,4-tetrahydroquinolines
Lin, Wen-Chung; Yang, Ding-Yah; Organic Letters 15 (2013) 4862–; doi:10.1021/ol402286d

data_1512352
_publ_section_title
;
 Visible Light Photoredox Catalysis: Synthesis of
 Indazolo[2,3-a]quinolines from
 2-(2-Nitrophenyl)-1,2,3,4-tetrahydroquinolines
;
_journal_issue                   18
_journal_name_full               'Organic Letters'
_journal_page_first              4862
_journal_paper_doi               10.1021/ol402286d
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C20 H21 N3 O4'
_chemical_formula_sum            'C20 H21 N3 O4'
_chemical_formula_weight         367.40
_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                83.624(12)
_cell_angle_beta                 76.161(9)
_cell_angle_gamma                82.285(9)
_cell_formula_units_Z            2
_cell_length_a                   9.2372(7)
_cell_length_b                   9.6199(14)
_cell_length_c                   10.3333(14)
_cell_measurement_reflns_used    2290
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.2150
_cell_measurement_theta_min      2.8279
_cell_volume                     880.52(19)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7884
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.28
_diffrn_reflns_theta_min         2.83
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99729
_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            orange
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0610P)^2^+0.6687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1472
_reflns_number_gt                3163
_reflns_number_total             4067
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402286d_si_005.cif
_cod_data_source_block           wc224
_cod_database_code               1512352