Povarov Reactions Involving 3-Aminocoumarins: Synthesis of 1,2,3,4-Tetrahydropyrido[2,3-c]coumarins and Pyrido[2,3-c]coumarins
Amit A. Kudale; Jamie Kendall; David O. Miller; Julie L. Collins; Graham J. Bodwell; Journal of Organic Chemistry 73 (2008) 8437–8447; doi:10.1021/jo801411p

data_4023804
_publ_section_title
;
 Povarov Reactions Involving 3-Aminocoumarins: Synthesis of
 1,2,3,4-Tetrahydropyrido[2,3-c]coumarins and Pyrido[2,3-c]coumarins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8437
_journal_page_last               8447
_journal_paper_doi               10.1021/jo801411p
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C22 H19 N O5 '
_chemical_formula_sum            'C22 H19 N O5'
_chemical_formula_weight         377.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             2004-01-07
_audit_creation_method           'by teXsan for Windows v1.06'
_cell_angle_alpha                90
_cell_angle_beta                 106.52(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.417(2)
_cell_length_b                   19.400(2)
_cell_length_c                   10.492(3)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    299.2
_cell_measurement_theta_max      20.8
_cell_measurement_theta_min      18.2
_cell_volume                     1837.7(6)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan for Windows 1.06 (MSC, 1997-1999)'
_computing_publication_material  'teXsan for Windows 1.06 (MSC, 1997-1999)'
_computing_structure_refinement  'teXsan for Windows 1.06 (MSC, 1997-1999)'
_computing_structure_solution
;
SHELX97 (Sheldrick, 1997)
;
_diffrn_ambient_temperature      299.2
_diffrn_measurement_device       'Rigaku AFC6S'
_diffrn_measurement_method       \w-2\q
_diffrn_orient_matrix_UB_11      -0.01901
_diffrn_orient_matrix_UB_12      0.01299
_diffrn_orient_matrix_UB_13      -0.09562
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_diffrn_orient_matrix_UB_33      -0.00027
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
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_diffrn_reflns_av_R_equivalents  0.02000
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_diffrn_reflns_limit_h_max       12
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_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4634
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        -0.10
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
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_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
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_refine_diff_density_max         1.12
_refine_diff_density_min         -0.56
_refine_ls_extinction_coef       0.0000005(1)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   2.626
_refine_ls_goodness_of_fit_ref   3.390
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1479
_refine_ls_R_factor_gt           0.0790
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00010|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0880
_refine_ls_wR_factor_ref         0.0840
_reflns_number_gt                2434
_reflns_number_total             4381
_reflns_threshold_expression     I>2.00\s(I)
_cod_data_source_file            jo801411p_si_002.cif
_cod_data_source_block           '_jk-3-40a'
_cod_original_sg_symbol_H-M      'P 21/n     '
_cod_original_formula_sum        'C22 H19 N O5 '
_cod_database_code               4023804