Competitive intramolecular nucleophilic aromatic substitution: a new route to coumarins
Alonso, Concepción; Olmstead, Marilyn M.; Nantz, Michael H.; Kurth, Mark J.; Chemical Communications  (2001) 639–; doi:10.1039/b009172n

data_7114768
_publ_contact_author             'Prof Mark J. Kurth'
_publ_section_title
;
 Competitive intramolecular nucleophilic aromatic substitution: a new
 route to coumarins
;
_journal_issue                   7
_journal_name_full               'Chemical Communications'
_journal_page_first              639
_journal_paper_doi               10.1039/b009172n
_journal_year                    2001
_chemical_formula_sum            'C21 H14 Cl N O3'
_chemical_formula_weight         363.78
_chemical_name_common            'Compound 3a'
_chemical_name_systematic
; 
phenylmethyl 9-chloro-6-oxa-10b-hydropyridino[1,2-a]quinoline-5-carboxylate 
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.273(8)
_cell_angle_beta                 79.502(9)
_cell_angle_gamma                68.701(10)
_cell_formula_units_Z            2
_cell_length_a                   7.1272(9)
_cell_length_b                   9.5407(12)
_cell_length_c                   13.1738(10)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      32.7
_cell_measurement_theta_min      3.45
_cell_volume                     808.95(17)
_computing_cell_refinement       'Siemens P3'
_computing_data_collection       'Siemens P3'
_computing_data_reduction        'Siemens XDISK'
_computing_molecular_graphics    'SHELXTL 5.03, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'nickel filter'
_diffrn_radiation_source         'Siemens rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2105
_diffrn_reflns_theta_full        56.09
_diffrn_reflns_theta_max         56.09
_diffrn_reflns_theta_min         3.46
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.280
_exptl_absorpt_correction_T_max  0.7715
_exptl_absorpt_correction_T_min  0.7408
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;XABS2: an empirical absorption correction program. Parkin, S.; Moezzi,
B.; Hope, H. J. Appl. Cryst. 1995, 28, 53-56.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         2105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+0.5496P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                1904
_reflns_number_total             2105
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b009172n.txt
_cod_data_source_block           mn1025
_cod_original_cell_volume        808.95(16)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7114768