Insertion-coupling-cycloisomerization domino synthesis and cation-induced halochromic fluorescence of 2,4-diarylpyrano[2,3-b]indoles.
Schönhaber, Jan; Frank, Walter; Müller, Thomas J J; Organic letters 12 (2010) 4122–4125; doi:10.1021/ol101709p

data_1503189
_publ_section_title
;
 Insertion-coupling-cycloisomerization domino synthesis and cation-induced
 halochromic fluorescence of 2,4-diarylpyrano[2,3-b]indoles.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4122
_journal_page_last               4125
_journal_paper_doi               10.1021/ol101709p
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C23 H15 N O'
_chemical_formula_sum            'C23 H15 N O'
_chemical_formula_weight         321.36
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.709(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1003(6)
_cell_length_b                   17.6993(10)
_cell_length_c                   10.2661(6)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.35
_cell_volume                     1653.58(19)
_computing_cell_refinement       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_collection       'IPDS Software (Stoe & Cie, 2000)'
_computing_data_reduction        'IPDS Software (Stoe & Cie, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       \f-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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21105
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.024
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.249
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0297
_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^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0664
_reflns_number_gt                2145
_reflns_number_total             2822
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101709p_si_002.cif
_cod_data_source_block           opus854
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503189