Total Synthesis of Antibacterial Polyketide Natural Product Thailandamide Lactone
Sharma, Himangshu; Mondal, Joyanta Mr.; Ghosh, Ananyo K. Mr.; Pal, Ritesh Ranjan Dr.; Goswami, Rajib Kumar; Chemical Science  (2022) –; doi:10.1039/D2SC04727F

data_1567829
_publ_section_title
;
 Total Synthesis of Antibacterial Polyketide Natural Product Thailandamide
 Lactone
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC04727F
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C26 H35 N O3 S2 Si'
_chemical_formula_sum            'C26 H35 N O3 S2 Si'
_chemical_formula_weight         501.76
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-05-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-07-05 deposited with the CCDC.	2022-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   18.235(3)
_cell_length_b                   18.235(3)
_cell_length_c                   7.1321(9)
_cell_measurement_reflns_used    7984
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.377
_cell_measurement_theta_min      2.23
_cell_volume                     2053.8(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-III PHOTON II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            22774
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.711
_diffrn_reflns_theta_min         2.234
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1368 before and 0.0905 after correction. The Ratio of minimum to maximum transmission is 0.8743. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       needle
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1840 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5650
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0275P)^2^+0.7416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.956
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4680
_reflns_number_total             5650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc04727f2.cif
_cod_data_source_block           rg070222_0m_a
_cod_original_cell_volume        2053.9(6)
_cod_database_code               1567829
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.890
_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. Uiso/Uaniso restraints and constraints
Uanis(C22A) = Uanis(C26A)
Uanis(C24B) = Uanis(C22A)
Uanis(C25A) = Uanis(C23B)
3. Others
 Sof(Si1)=Sof(C24A)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C21A)=
 Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C25A)=Sof(H25A)=Sof(H25B)=Sof(H25C)=
 Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C26A)=Sof(H26A)=Sof(H26B)=
 Sof(H26C)=1-FVAR(1)
 Sof(Si00)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(H28C)=Sof(C21B)=Sof(C22B)=Sof(H22G)=Sof(H22H)=Sof(H22I)=Sof(C24B)=
 Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C23B)=Sof(H23D)=Sof(H23E)=Sof(H23F)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
4.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C12(H12A,H12B), C9(H9A,H9B), C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C5(H5), C2(H2), C1(H1), C16(H16), C4(H4), C19(H19), C3(H3), C17(H17)
4.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C28(H28A,H28B,H28C), C22A(H22D,H22E,H22F), C21A(H21A,
 H21B,H21C), C25A(H25A,H25B,H25C), C22B(H22G,H22H,H22I), C23A(H23A,H23B,H23C),
 C24B(H24A,H24B,H24C), C26A(H26A,H26B,H26C), C23B(H23D,H23E,H23F)
4.e Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_olex2_submission_special_instructions 'No special instructions were received'