Twelve-Step Asymmetric Synthesis of (-)-Nodulisporic Acid C.
Godfrey, Nicole A.; Schatz, Devon J.; Pronin, Sergey V.; Journal of the American Chemical Society 140 (2018) 12770–12774; doi:10.1021/jacs.8b09965

data_4133425
_publ_section_title
;
 Twelve-Step Asymmetric Synthesis of (-)-Nodulisporic Acid C.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12770
_journal_page_last               12774
_journal_paper_doi               10.1021/jacs.8b09965
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C25 H37 Br Cl N O4 Si'
_chemical_formula_weight         559.00
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9555(7)
_cell_length_b                   16.5243(15)
_cell_length_c                   21.253(2)
_cell_measurement_reflns_used    8396
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.28
_cell_volume                     2793.9(4)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15707
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.561
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.639
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.945
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.18(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0734
_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^)+(0.0643P)^2^+13.7606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1781
_refine_ls_wR_factor_ref         0.1815
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5125
_reflns_number_total             5691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b09965_si_004.cif
_cod_data_source_block           svp9
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not_measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
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_cod_database_code               4133425
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.581
_shelx_estimated_absorpt_t_max   0.856
_exptl_absorpt_special_details
; 
Reflections not merged 
17205 Corrected reflections written to file svp9bs.hkl 
Estimated minimum and maximum transmission:  0.5129  0.7456 
The ratio (0.6879) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.2000 
Lambda/2 correction factor = 0.00150 
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_shelx_res_checksum              3905
_shelx_hkl_checksum              56844