Coupling-Isomerization-N,S-Ketene Acetal-Addition Sequences- A Three-Component Approach to Highly Fluorescent Pyrrolo[2,3-b]pyridines, [1,8]Naphthyridines, and Pyrido[2,3-b]azepines
Oana G. Schramm; Née Dediu; Thomas Oeser; Thomas J. J. Müller; Journal of Organic Chemistry 71 (2006) 3494–3500; doi:10.1021/jo0602726

data_4021666
_publ_contact_author_address
;
Organisch-Chemisches Institut
Universit\"at Heidelberg
Im Neuenheimer Feld 270
D-69120 Heidelberg
;
_publ_contact_author_email       thomas.oeser@oci.uni-heidelberg.de
_publ_contact_author_fax         '+49 6221 544205'
_publ_contact_author_name        'Dr. Thomas Oeser'
_publ_contact_author_phone       '+49 6221 548482'
_publ_section_title
;
 Coupling-Isomerization-N,S-Ketene Acetal-Addition Sequences-
 A Three-Component Approach to Highly Fluorescent
 Pyrrolo[2,3-b]pyridines, [1,8]Naphthyridines, and
 Pyrido[2,3-b]azepines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3494
_journal_page_last               3500
_journal_paper_doi               10.1021/jo0602726
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C29 H25 N3 O'
_chemical_formula_weight         431.52
_chemical_name_systematic
; 
4-[9-Methyl-2-(4-phenoxy-phenyl)-6,7,8,9-tetrahydro-
5H-pyrido[2,3-b]azepin-4-yl]-benzonitrile 
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.0
_cell_angle_beta                 94.469(3)
_cell_angle_gamma                90.0
_cell_formula_units_Z            16
_cell_length_a                   11.253(1)
_cell_length_b                   39.851(6)
_cell_length_c                   20.366(3)
_cell_measurement_reflns_used    5440
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.74
_cell_measurement_theta_min      2.20
_cell_volume                     9105(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0927
_diffrn_reflns_av_sigmaI/netI    0.1741
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            95629
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             3648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2385
_refine_ls_number_reflns         44574
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1726
_refine_ls_R_factor_gt           0.0735
_refine_ls_shift/su_max          0.613
_refine_ls_shift/su_mean         0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1718
_reflns_number_gt                21494
_reflns_number_total             44574
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0602726si20060215_034005_1.cif
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               4021666