Synthesis of the fused polyether core of hemibrevetoxin B by two-directional ring-closing metathesis.
Clark, J. Stephen; Grainger, Damian M.; Ehkirch, Alexandra A.-C.; Blake, Alexander J.; Wilson, Claire; Organic letters 9 (2007) 1033–1036; doi:10.1021/ol0630651

data_1505307
_publ_section_title
;
 Synthesis of the fused polyether core of hemibrevetoxin B by
 two-directional ring-closing metathesis.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1033
_journal_page_last               1036
_journal_paper_doi               10.1021/ol0630651
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C13 H20 O5'
_chemical_formula_weight         256.29
_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, Me from difmap'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.804(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0910(14)
_cell_length_b                   7.4742(11)
_cell_length_c                   9.4591(14)
_cell_measurement_reflns_used    1174
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.25
_cell_volume                     640.47(17)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_publication_material  'enCIFer (CCDC, 2003); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2281
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.11
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1225
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0483P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0753
_reflns_number_gt                1112
_reflns_number_total             1225
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol0630651si20061221_114143.cif
_cod_data_source_block           14
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1505307