Access to isocarbacyclin derivatives via substrate-controlled enolate formation: total synthesis of 15-deoxy-16-(m-tolyl)- 17,18,19,20-tetranorisocarbacyclin
Sheddan, Neil A.; Mulzer, Johann; Organic letters 7 (2005) 5115–5118; doi:10.1021/ol0515762

data_1506695
_publ_section_title
;
 Access to isocarbacyclin derivatives via substrate-controlled enolate
 formation: total synthesis of 15-deoxy-16-(m-tolyl)-
 17,18,19,20-tetranorisocarbacyclin
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5115
_journal_page_last               5118
_journal_paper_doi               10.1021/ol0515762
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_sum            'C35 H41 F3 O5 S Si'
_chemical_formula_weight         658.83
_chemical_melting_point          384.1(10)
_chemical_name_systematic
;
(3aS,5R,6S,6aS)-5-(tert-butyldimethylsilyloxy)-6-
(trityloxymethyl)-1,3a,4,5,6,6a-hexahydropentalen-
2-yl trifluoromethanesulfonate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.605(2)
_cell_length_b                   15.000(3)
_cell_length_c                   21.184(4)
_cell_measurement_temperature    150(2)
_cell_volume                     3369.8(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Kappa-Nonius diffractometer'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10201
_diffrn_reflns_theta_full        30.51
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         3.46
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9633
_exptl_absorpt_correction_T_min  0.8954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_recrystallization_method methanol
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       0.0054(8)
_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   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         10201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0550P)^2^+0.7500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                8980
_reflns_number_total             10201
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0515762si20050706_045554.cif
_cod_data_source_block           nas205
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '383.15-385.15' was changed to
'384.1(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3369.9(12)
_cod_database_code               1506695