Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles
Mahiout, Zahia; Lomberget, Thierry; Goncalves, Sylvie; Barret, Roland; Organic & Biomolecular Chemistry 6 (2008) 1364–1376; doi:10.1039/b719776d

data_7150875
_publ_section_title
;
 Solvent-dependent oxidations of 5- and 6-azaindoles to
 trioxopyrrolopyridines and functionalised azaindoles
;
_journal_issue                   8
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              1364
_journal_page_last               1376
_journal_paper_doi               10.1039/b719776d
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C9 H6 N2 O5'
_chemical_formula_sum            'C9 H6 N2 O5'
_chemical_formula_weight         222.16
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             06-11-23
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                111.47
_cell_angle_beta                 94.77
_cell_angle_gamma                94.31
_cell_formula_units_Z            2
_cell_length_a                   5.35
_cell_length_b                   8.79
_cell_length_c                   10.58
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     458.412
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3192
_diffrn_reflns_theta_full        25.246
_diffrn_reflns_theta_max         27.743
_diffrn_reflns_theta_min         2.084
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9909
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_description       needle
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0578
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.000264
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.603 0.477 0.354
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1150
_refine_ls_wR_factor_gt          0.0567
_refine_ls_wR_factor_ref         0.0567
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              10
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1005
_reflns_number_total             2078
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.628(3)
_oxford_structure_analysis_title 'scale in P -1'
_cod_data_source_file            b719776d.txt
_cod_data_source_block           1
_cod_original_cell_volume        458.77634(2)
_cod_original_sg_symbol_Hall     '- P1'
_cod_database_code               7150875