Base-Induced Chemiluminescent Decomposition of Bicyclic Dioxetanes Bearing a (Benzothiazol-2-yl)-3-hydroxyphenyl Group: A Radiationless Pathway Leading to Marked Decline of Chemiluminescence Efficiency
Masatoshi, Tanimura; Nobuko Watanabe; Hisako K. Ijuin; Masakatsu Matsumoto; Journal of Organic Chemistry 77 (2012) 4725–4731; doi:10.1021/jo300417e

data_4027196
_publ_contact_author_email       matsumo-chem@kanagawa-u.ac.jp
_publ_contact_author_fax         81(463)589684
_publ_contact_author_name        'Professor Masakatsu Matsumoto'
_publ_contact_author_phone       81(463)594111
_publ_section_title
;
 Base-Induced Chemiluminescent Decomposition of Bicyclic Dioxetanes
 Bearing a (Benzothiazol-2-yl)-3-hydroxyphenyl Group: A Radiationless
 Pathway Leading to Marked Decline of Chemiluminescence Efficiency
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4725
_journal_page_last               4731
_journal_paper_doi               10.1021/jo300417e
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C23 H25 N O4 S'
_chemical_formula_sum            'C23 H25 N O4 S'
_chemical_formula_weight         411.50
_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                 90.084(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.980(2)
_cell_length_b                   20.081(6)
_cell_length_c                   12.971(4)
_cell_measurement_reflns_used    7783
_cell_measurement_temperature    140
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     2078.6(10)
_computing_cell_refinement
;
Rigaku CrystalClear-SM Expert 2.0 r1
;
_computing_data_collection
;
Rigaku CrystalClear-SM Expert 2.0 r1
;
_computing_data_reduction
;
Rigaku CrystalClear-SM Expert 2.0 r1
;
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      140
_diffrn_detector_area_resol_mean 14.8920
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Rigaku CrystalClear-SM Expert 2.0 r1
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22357
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       Column
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         4764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0806
_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^)+(0.1489P)^2^+0.7561P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2453
_refine_ls_wR_factor_ref         0.2693
_reflns_number_gt                3342
_reflns_number_total             4764
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300417e_si_003.cif
_cod_data_source_block           1d
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027196