Asymmetric synthesis of a stereopentade fragment toward latrunculins
Joyeux, Benjamin; Gamet, Antoine; Casaretto, Nicolas; Nay, Bastien; Beilstein Journal of Organic Chemistry 19 (2023) 428–433; doi:10.3762/bjoc.19.32

data_4039019
_publ_section_title
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 Asymmetric synthesis of a stereopentade fragment toward latrunculins
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_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              428
_journal_page_last               433
_journal_paper_doi               10.3762/bjoc.19.32
_journal_volume                  19
_journal_year                    2023
_chemical_formula_moiety         'C12 H15 N O3 S'
_chemical_formula_sum            'C12 H15 N O3 S'
_chemical_formula_weight         253.31
_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             2021-01-07
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.936(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.5075(16)
_cell_length_b                   5.6395(15)
_cell_length_c                   19.524(6)
_cell_measurement_reflns_used    1897
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      21.838
_cell_measurement_theta_min      3.138
_cell_volume                     605.0(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker 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  0.0876
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9492
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_min         2.091
_diffrn_source_current           31.0
_diffrn_source_power             1.705
_diffrn_source_voltage           55.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.263
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1259 before and 0.0932 after correction.
The Ratio of minimum to maximum transmission is 0.7240.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.168
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0832
_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^)+(0.1336P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2167
_refine_ls_wR_factor_ref         0.2346
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1979
_reflns_number_total             2769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-19-32-S2.cif
_cod_data_source_block           bjm04_0m
_cod_database_code               4039019
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.913
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.0(3)
 0.0(3)
2. 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
3. Restrained distances
 S1-C2A \\sim S1-C2
 with sigma of 0.02
 C3-C2A \\sim C3-C2
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C2A \\sim C2: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
5. Others
 Sof(H3B)=Sof(C2)=Sof(H2A)=Sof(H2B)=1-FVAR(1)
 Sof(H3A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C3(H3A), C3(H3B)
6.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C2A(H2AA,H2AB), C2(H2A,H2B)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11)
6.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
6.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              53817
_shelx_hkl_checksum              89450
_olex2_submission_special_instructions 'No special instructions were received'