Taxadiene Synthase-Catalyzed Cyclization of 6-Fluorogeranylgeranyl Diphosphate to 7-Fluoroverticillenes
Yinghua Jin; David C. Williams; Rodney Croteau; Robert M. Coates; Journal of the American Chemical Society 127 (2005) 7834–7842; doi:10.1021/ja050592r

data_4111726
_publ_contact_author
; 
Robert M. Coates 
Department of Chemistry
University of Illinois
337B Roger Adams Lab
600 South Mathews Avenue
Urbana, IL 61801
USA
;
_publ_contact_author_email       coates@scs.uiuc.edu
_publ_contact_author_fax         '1  217 244 8024'
_publ_contact_author_phone       '1  217 333 4280'
_publ_section_title
;
 Taxadiene Synthase-Catalyzed Cyclization of 6-Fluorogeranylgeranyl
 Diphosphate to 7-Fluoroverticillenes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7834
_journal_page_last               7842
_journal_paper_doi               10.1021/ja050592r
_journal_volume                  127
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H37 I O2'
_chemical_formula_sum            'C27 H37 I O2'
_chemical_formula_weight         520.47
_chemical_name_common            '(+)-verticillyl p-iodobenzoate'
_chemical_name_systematic
;
(1S,3E,7E,11S,12S)-4,8,12,15,15-pentamethylbicyclo[9.3.1]pentadeca-
3,7-dien-12-yl 4-iodobenzoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2004-08-18   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.510(3)
_cell_length_b                   15.122(6)
_cell_length_c                   21.737(9)
_cell_measurement_reflns_used    930
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      22.80
_cell_measurement_theta_min      2.31
_cell_volume                     2468.6(17)
_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 V6.10 (Bruker, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL V6.10 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.10 (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  g84ba
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21282
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         26.32
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        2.6
_diffrn_standards_interval_time  306
_diffrn_standards_number         240
_exptl_absorpt_coefficient_mu    1.317
_exptl_absorpt_correction_T_max  0.9139
_exptl_absorpt_correction_T_min  0.5552
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       columnar
_exptl_crystal_F_000             1072
_exptl_crystal_id                g84ba
_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 0) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.016(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.880
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         5012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0592
_reflns_number_gt                3396
_reflns_number_total             5012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja050592rsi20050203_080552.cif
_cod_data_source_block           g84ba
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4111726