Biomimetic Synthesis of Pyrone-Derived Natural Products: Exploring Chemical Pathways from a Unique Polyketide Precursor
Serena J. Eade; Magnus W. Walter; Colin Byrne; Barbara Odell; Raphaël Rodriguez; Jack E. Baldwin; Robert M.Adlington; John E. Moses; Journal of Organic Chemistry 73 (2008) 4830–4839; doi:10.1021/jo800220w

data_4023503
_publ_section_title
;
 Biomimetic Synthesis of Pyrone-Derived Natural Products:
 Exploring Chemical Pathways from a Unique Polyketide Precursor
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4830
_journal_page_last               4839
_journal_paper_doi               10.1021/jo800220w
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C11 H13 Br O3 '
_chemical_formula_sum            'C11 H13 Br O3'
_chemical_formula_weight         273.13
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             05-16-05
_audit_creation_method           CRYSTALS_ver_12-03-99
_cell_angle_alpha                90
_cell_angle_beta                 94.7722(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.0877(2)
_cell_length_b                   7.3634(2)
_cell_length_c                   37.9309(5)
_cell_measurement_reflns_used    20778
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     2251.07(9)
_computing_cell_refinement
; 
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) 
;
_computing_data_collection
; 
KappaCCD software 'Collect' (Nonius, 2000) 
;
_computing_data_reduction
; 
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) 
;
_computing_publication_material
; 
CRYSTALS (Watkin et al, 2001) 
;
_computing_structure_refinement
; 
CRYSTALS (Watkin et al, 2001) 
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
; 
Nonius KappaCCD 
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            20778
_diffrn_reflns_theta_full        27.482
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         5.127
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.636
_exptl_absorpt_correction_T_max  0.83
_exptl_absorpt_correction_T_min  0.48
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_description       ' plate '
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_thermal_history
; 
The material was crystallised at ambient temperature. A suitable crystal 
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. 
;
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.52
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1111
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001970
_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: 
 0.445 0.114 0.156 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0720
_refine_ls_wR_factor_gt          0.0371
_refine_ls_wR_factor_ref         0.0371
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              49
_reflns_limit_l_min              0
_reflns_number_gt                3084
_reflns_number_total             5121
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            jo800220w-File002.cif
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        ' C11 H13 Br O3 '
_cod_database_code               4023503