Spectral-Structural Effects of the Keto-Enol-Enolate and Phenol-Phenolate Equilibria of Oxyluciferin
Panče Naumov; Manoj Kochunnoonny; Journal of the American Chemical Society 132 (2010) 11566–11579; doi:10.1021/ja102885g

data_4102866
_publ_section_title
;
 Spectral-Structural Effects of the Keto-Enol-Enolate and Phenol-Phenolate
 Equilibria of Oxyluciferin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11566
_journal_page_last               11579
_journal_paper_doi               10.1021/ja102885g
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         C12H12N2OS2
_chemical_formula_sum            'C12 H12 N2 O S2'
_chemical_formula_weight         264.36
_chemical_name_common            4-dehydroxy-5,5-dimethyloxyluciferin
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3882(3)
_cell_length_b                   10.7673(4)
_cell_length_c                   20.4740(8)
_cell_measurement_temperature    293(2)
_cell_volume                     2510.53(15)
_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 0.805
_diffrn_measured_fraction_theta_max 0.805
_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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4708
_diffrn_reflns_theta_full        26.53
_diffrn_reflns_theta_max         26.53
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'oval prism'
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0000(3)
_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   0.972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          2.827
_refine_ls_shift/su_mean         0.018
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                1259
_reflns_number_total             2101
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja102885g_si_004.cif
_cod_data_source_block           oza1
_cod_original_formula_sum        C12H12N2OS2
_cod_database_code               4102866