Diastereoselective allylation-based asymmetric total synthesis of 1,10-<i>seco</i>-guaianolides.
Fernandes, Rodney A.; Ranjan, Ravikant S.; Organic & biomolecular chemistry 22 (2024) 811–822; doi:10.1039/d3ob02013d

data_7159729
_publ_section_title
;
 Diastereoselective allylation-based asymmetric total synthesis of
 1,10-<i>seco</i>-guaianolides.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              811
_journal_page_last               822
_journal_paper_doi               10.1039/d3ob02013d
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C11 H12 O4 S'
_chemical_formula_sum            'C11 H12 O4 S'
_chemical_formula_weight         240.27
_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
_audit_creation_date             2023-06-02
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-06-02 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5447(4)
_cell_length_b                   10.2606(5)
_cell_length_c                   12.5052(5)
_cell_measurement_reflns_used    4409
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.2910
_cell_measurement_theta_min      2.8770
_cell_volume                     1096.38(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -132.21   3.79   1.00    2.00  16.12 -12.98 -59.25    --   136
  2  \f    173.44 333.44   1.00    2.00  77.88 -12.98  31.50    --   160
  3  \w     -7.63  15.37   1.00    2.00    --  -12.98 -59.25  20.08   23
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0559298000
_diffrn_orient_matrix_UB_12      0.0510606000
_diffrn_orient_matrix_UB_13      0.0003039000
_diffrn_orient_matrix_UB_21      -0.0493466000
_diffrn_orient_matrix_UB_22      0.0371997000
_diffrn_orient_matrix_UB_23      0.0338904000
_diffrn_orient_matrix_UB_31      0.0364047000
_diffrn_orient_matrix_UB_32      -0.0280069000
_diffrn_orient_matrix_UB_33      0.0455173000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12004
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.413
_diffrn_reflns_theta_min         2.568
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1030 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0497P)^2^+0.1421P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0998
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.765
_reflns_number_gt                3003
_reflns_number_total             3579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02013d2.cif
_cod_data_source_block           raf_rsr_s_autored
_cod_depositor_comments
'Adding full bibliography for 7159727--7159729.cif.'
_cod_database_code               7159729
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.943
_reflns_odcompleteness_completeness 89.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.34
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C4(H4A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C10(H10)
2.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_shelx_res_checksum              24497
_shelx_hkl_checksum              93747
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.624