Regioselectivity and stereoselectivity of dioxygenase catalysed cis-dihydroxylation of mono- and tri-cyclic azaarene substrates
Boyd, Derek R.; Sharma, Narain D.; Coen, Gerard P.; Hempenstall, Francis; Ljubez, Vera; Malone, John F.; Allen, Christopher C. R.; Hamilton, John T. G.; Organic & Biomolecular Chemistry 6 (2008) 3957–3966; doi:10.1039/b810235j

data_7151003
_publ_section_title
;
 Regioselectivity and stereoselectivity of dioxygenase catalysed
 cis-dihydroxylation of mono- and tri-cyclic azaarene substrates
;
_journal_issue                   21
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3957
_journal_page_last               3966
_journal_paper_doi               10.1039/b810235j
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H11 N O2'
_chemical_formula_sum            'C10 H11 N O2'
_chemical_formula_weight         177.20
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.18(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   13.076(4)
_cell_length_b                   4.980(2)
_cell_length_c                   21.362(11)
_cell_measurement_temperature    293(2)
_cell_volume                     1354.4(10)
_computing_cell_refinement       'Siemens P3/V2000'
_computing_data_collection       'Siemens P3/V2000'
_computing_data_reduction        'Siemens P3/V2000'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Siemens P3 diffractometer'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3971
_diffrn_reflns_theta_full        55.05
_diffrn_reflns_theta_max         55.05
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 99
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(18)
_refine_ls_extinction_coef       0.081(7)
_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   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         3307
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0741
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1732P)^2^+0.3283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2037
_refine_ls_wR_factor_ref         0.2061
_reflns_number_gt                3210
_reflns_number_total             3307
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b810235j.txt
_cod_data_source_block           2e
_cod_original_cell_volume        1354.5(10)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7151003