Structure and Spectroscopy of Oxyluciferin, the Light Emitter of the Firefly Bioluminescence
Panče Naumov; Yutaka Ozawa; Kei Ohkubo; Shunichi Fukuzumi; Journal of the American Chemical Society 131 (2009) 11590–11605; doi:10.1021/ja904309q

data_4104873
_publ_section_title
;
 Structure and Spectroscopy of Oxyluciferin, the Light Emitter of the
 Firefly Bioluminescence
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11590
_journal_page_last               11605
_journal_paper_doi               10.1021/ja904309q
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C10 H6 N2 O2 S2'
_chemical_formula_weight         250.29
_chemical_name_common            'firefly oxylcuiferin'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 99.260(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8806(4)
_cell_length_b                   18.8242(14)
_cell_length_c                   11.1298(8)
_cell_measurement_temperature    293(2)
_cell_volume                     1009.21(13)
_computing_cell_refinement       'APEX2 software (Bruker, 2007)'
_computing_data_collection       'APEX2 software (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX2 diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'multilayer confocal TXS mirror'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14599
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.510
_exptl_absorpt_correction_T_max  0.9676
_exptl_absorpt_correction_T_min  0.8579
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0625P)^2^+0.8795P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1412
_reflns_number_gt                1376
_reflns_number_total             2056
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja904309q_si_002.cif
_cod_data_source_block           oxyl5_0m
_cod_database_code               4104873