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_4021670
_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            'C22 H23 N3 O'
_chemical_formula_weight         345.43
_chemical_name_systematic
;
2-(4-Methoxy-phenyl)-9-methyl-4-pyridin-2-yl-6,7,8,9-
tetrahydro-5H-pyrido[2,3-b]azepine
;
_space_group_IT_number           2
_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                66.502(2)
_cell_angle_beta                 71.853(2)
_cell_angle_gamma                67.098(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9544(6)
_cell_length_b                   10.4943(7)
_cell_length_c                   11.4673(9)
_cell_measurement_temperature    200(2)
_cell_volume                     894.61(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      200(2)
_diffrn_measured_fraction_theta_full 0.784
_diffrn_measured_fraction_theta_max 0.784
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3467
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0703P)^2^+0.0377P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                2462
_reflns_number_total             3246
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0602726si20060215_034005_5.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4021670