One-pot synthesis of coumarin-based oxazabicyclic and oxazatricyclic compounds and their fluorescence redox switching properties.
Lin, Chi-Hui; Jhang, Jing-Fu; Yang, Ding-Yah; Organic letters 11 (2009) 4064–4067; doi:10.1021/ol901505e

data_1504106
_publ_section_title
;
 One-pot synthesis of coumarin-based oxazabicyclic and oxazatricyclic
 compounds and their fluorescence redox switching properties.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4064
_journal_page_last               4067
_journal_paper_doi               10.1021/ol901505e
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C27 H26 N2 O3'
_chemical_formula_sum            'C27 H26 N2 O3'
_chemical_formula_weight         426.50
_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'
_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                 101.355(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.824(5)
_cell_length_b                   14.282(6)
_cell_length_c                   16.681(7)
_cell_measurement_reflns_used    1780
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.205
_cell_measurement_theta_min      2.398
_cell_volume                     2528.2(19)
_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      297(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_av_sigmaI/netI    0.1085
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13740
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.89
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.532507
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   empirical
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_platon_squeeze_details          ' '
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.0052(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1763
_refine_ls_R_factor_gt           0.0908
_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^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2069
_refine_ls_wR_factor_ref         0.2281
_reflns_number_gt                1794
_reflns_number_total             4967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901505e_si_004.cif
_cod_data_source_block           cf999m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constro' was replaced with the
value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_cell_volume        2528.3(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1504106