16-Aza-ent-beyerane and 16-Aza-ent-trachylobane: Potent Mechanism-Based Inhibitors of Recombinantent-Kaurene Synthase from Arabidopsis thaliana
Arnab Roy; Frank G. Roberts; P. Ross Wilderman; Ke Zhou; Reuben J. Peters; Robert M. Coates; Journal of the American Chemical Society 129 (2007) 12453–12460; doi:10.1021/ja072447e

data_4110001
_publ_section_title
;
 16-Aza-ent-beyerane and 16-Aza-ent-trachylobane: Potent Mechanism-Based
 Inhibitors of Recombinantent-Kaurene Synthase from Arabidopsis thaliana
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12453
_journal_page_last               12460
_journal_paper_doi               10.1021/ja072447e
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H32 N, C6 H2 N3 O7'
_chemical_formula_sum            'C25 H34 N4 O7'
_chemical_formula_weight         502.56
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2005-03-30   text and data added, roy 
2006-12-19   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.052(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.701(5)
_cell_length_b                   7.179(3)
_cell_length_c                   16.525(8)
_cell_measurement_reflns_used    889
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      22.63
_cell_measurement_theta_min      2.81
_cell_volume                     1231.5(10)
_computing_cell_refinement       'SAINT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.22 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2001)'
_computing_publication_material  'XCIF (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  g61eam
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9799
_diffrn_reflns_theta_full        25.30
_diffrn_reflns_theta_max         25.30
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  305
_diffrn_standards_number         128
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.99021
_exptl_absorpt_correction_T_min  0.95830
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SHELXTL/XPREP (Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       tabular
_exptl_crystal_F_000             536
_exptl_crystal_id                g61eam
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-1 0 -1) scattering planes 
roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack (1983),  2006 Friedels'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0649P)^2^+0.0137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1120
_reflns_number_gt                1780
_reflns_number_total             2444
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja072447esi20070407_050039.cif
_cod_data_source_block           g61eam
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4110001