The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation
John A. Enquist Jr; Brian M. Stoltz; Nature 453 (2008) 1228–1231; doi:10.1038/nature07046

data_1547152
_publ_section_title
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 The total synthesis of (-)-cyanthiwigin F by means of double catalytic
 enantioselective alkylation
;
_journal_name_full               Nature
_journal_page_first              1228
_journal_page_last               1231
_journal_paper_doi               10.1038/nature07046
_journal_volume                  453
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H24 O2'
_chemical_formula_sum            'C17 H24 O2'
_chemical_formula_weight         260.36
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4937(2)
_cell_length_b                   9.0345(2)
_cell_length_c                   21.4487(5)
_cell_measurement_reflns_used    5024
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.79
_cell_measurement_theta_min      4.12
_cell_volume                     1452.12(6)
_computing_cell_refinement       'Bruker SAINT v6.45A'
_computing_data_collection       'Bruker SMART v5.630'
_computing_data_reduction        'Bruker SAINT v6.45A'
_computing_molecular_graphics    'Bruker XP v5.1'
_computing_publication_material  'Bruker XCIF v6.12'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       '\w scans at 7 \f settings'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7914
_diffrn_reflns_theta_full        65.79
_diffrn_reflns_theta_max         65.79
_diffrn_reflns_theta_min         4.12
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8017
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.155
_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   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.394
_refine_ls_hydrogen_treatment    Unrestrained
_refine_ls_matrix_type           'Full matrix'
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.394
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/s^2^(Fo^2^)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0686
_reflns_number_gt                2083
_reflns_number_total             2344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jae01_664430.CIF
_cod_data_source_block           1
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

'_refine_ls_weighting_scheme' value 'Sigma' changed to 'sigma'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_atom_sites_solution_primary' value 'Direct methods' was changed to
'direct'.

'_atom_sites_solution_secondary' value 'Difference Fourier map' was
changed to 'difmap'.

'_atom_sites_solution_hydrogens' value 'Difference Fourier map' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1547152