Preparation of a Family of 10-Hydroxybenzo[h]quinoline Analogues via a Modified Sanford Reaction and Their Excited State Intramolecular Proton Transfer Properties
Joanna Piechowska; Daniel T. Gryko; Journal of Organic Chemistry 76 (2011) 10220–10228; doi:10.1021/jo202072d

data_4026811
_publ_section_title
;
 Preparation of a Family of 10-Hydroxybenzo[h]quinoline Analogues via a
 Modified Sanford Reaction and Their Excited State Intramolecular Proton
 Transfer Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10220
_journal_page_last               10228
_journal_paper_doi               10.1021/jo202072d
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.288(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3170(2)
_cell_length_b                   10.7960(3)
_cell_length_c                   15.1900(5)
_cell_measurement_reflns_used    2245
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1075.83(6)
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_molecular_graphics
;
Ortep-3 for Windows, L.J.Farrugia (1997) J.Appl.Cryst. 30, 565,
ORTEP III (Burnett, Johnson, 1996)
;
_computing_publication_material
;
SHELXL-97 (Sheldrick, 1997),
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       '\k-geometry diffractometr'
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector \w 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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2924
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0516P)^2^+0.3578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                1400
_reflns_number_total             1528
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo202072d_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        1075.83(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026811