Asymmetric Total Synthesis of Inthomycins A, B, and C.
Kim, Jae Hyun; Song, Yeonghun; Kim, Min Jung; Kim, Sanghee; The Journal of organic chemistry 85 (2020) 4795–4806; doi:10.1021/acs.joc.0c00017

data_4038098
_publ_section_title
;
 Asymmetric Total Synthesis of Inthomycins A, B, and C.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4795
_journal_page_last               4806
_journal_paper_doi               10.1021/acs.joc.0c00017
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H35 F3 O6 Si'
_chemical_formula_sum            'C25 H35 F3 O6 Si'
_chemical_formula_weight         516.62
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-31
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:19:11 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.859(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.1127(7)
_cell_length_b                   7.7038(4)
_cell_length_c                   14.0568(7)
_cell_measurement_reflns_used    4219
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      25.4390
_cell_measurement_theta_min      3.0120
_cell_volume                     1406.65(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -87.00 -62.00   1.00    6.00    --  -11.20 155.00 -79.00   25
  2  \w      7.00  32.00   1.00    6.00    --   11.83-120.00  39.00   25
  3  \w     27.00  54.00   1.00    6.00    --   11.83-155.00-117.00   27
  4  \w    -83.00  15.00   1.00    6.00    --  -11.20 -57.00 120.00   98
  5  \w      3.00  30.00   1.00    6.00    --  -11.20 -99.00 -90.00   27
  6  \w    -84.00   3.00   1.00    6.00    --  -11.20 -38.00   0.00   87
  7  \w    -33.00  -4.00   1.00    6.00    --   11.83 -38.00  60.00   29
  8  \w    -20.00  25.00   1.00    6.00    --   11.83 -99.00  30.00   45
  9  \w    -56.00  33.00   1.00    6.00    --   11.83 -38.00-120.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0369272000
_diffrn_orient_matrix_UB_12      0.0641895000
_diffrn_orient_matrix_UB_13      -0.0072827000
_diffrn_orient_matrix_UB_21      -0.0171866000
_diffrn_orient_matrix_UB_22      -0.0017023000
_diffrn_orient_matrix_UB_23      -0.0500764000
_diffrn_orient_matrix_UB_31      -0.0363808000
_diffrn_orient_matrix_UB_32      0.0659814000
_diffrn_orient_matrix_UB_33      0.0057943000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13590
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.286
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.583
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.193
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1337 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4948
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0386P)^2^+0.1360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3977
_reflns_number_total             4948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00017_si_002.cif
_cod_data_source_block           exp_1421-1
_cod_depositor_comments          'Adding full bibliography for 4038098.cif.'
_cod_database_code               4038098
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C25H35F3O6Si
_chemical_oxdiff_usercomment     JH2-IV-63
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.924
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C24(H24), C21(H21), C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C), C8(H8A,H8B,H8C), C1(H1A,H1B,H1C),
 C14(H14A,H14B,H14C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C11(H11A,H11B,
 H11C), C13(H13A,H13B,H13C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              74753
_shelx_hkl_checksum              52336
_olex2_date_sample_data_collection 2019-12-26
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.562