Streamlined Symmetrical Total Synthesis of Disorazole B1 and Design, Synthesis, and Biological Investigation of Disorazole Analogues
Nicolaou, K. C.; Krieger, Johannes; Murhade, Ganesh M.; Subramanian, Parthasarathi; Dherange, Balu D.; Vourloumis, Dionisios; Munneke, Stefan; Lin, Baiwei; Gu, Christine; Sarvaiaya, Hetal; Sandoval, Joseph; Zhang, Zhaomei; Aujay, Monette; Purcell, James W.; Gavrilyuk, Julia; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c07094

data_4135213
_publ_section_title
;
 Streamlined Symmetrical Total Synthesis of Disorazole B1 and Design,
 Synthesis, and Biological Investigation of Disorazole Analogues
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c07094
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H49 N O3 S Si'
_chemical_formula_sum            'C25 H49 N O3 S Si'
_chemical_formula_weight         471.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-13
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.7870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.1760(2)
_cell_length_b                   9.9480(2)
_cell_length_c                   15.9081(3)
_cell_measurement_reflns_used    9546
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      71.106
_cell_measurement_theta_min      2.818
_cell_volume                     1431.00(5)
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23501
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         71.162
_diffrn_reflns_theta_min         2.819
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.580
_exptl_absorpt_correction_T_max  0.5860
_exptl_absorpt_correction_T_min  0.4939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0591 before and 0.0343 after correction. The Ratio of minimum to maximum transmission is 0.8428. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2409 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0229
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0357P)^2^+0.2165P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0600
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                5285
_reflns_number_total             5361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c07094_si_002.cif
_cod_data_source_block           kcnic015
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               4135213
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.884
_shelx_estimated_absorpt_t_min   0.733
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C23A-C22A \\sim C23-C22 \\sim C24A-C22A \\sim C24-C22 \\sim C25A-C22A \\sim
C25-C22
 with sigma of 0.01
 Si1-C22 \\sim Si1-C22A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C22A) = Uanis(C22)
Uanis(C23A) = Uanis(C23)
4. Others
 Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C22A)=Sof(C25A)=Sof(H25D)=
 Sof(H25E)=Sof(H25F)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(C22)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C24)=Sof(H24A)=Sof(H24B)=
 Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C9(H9), C11(H11), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C10(H10A,H10B), C12(H12A,H12B)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C),
 C23A(H23D,H23E,H23F), C25A(H25D,H25E,H25F), C24A(H24D,H24E,H24F)
5.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              53857
_shelx_hkl_checksum              74937
_olex2_submission_special_instructions 'No special instructions were received'