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_7159728
_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         'C17 H16 O4'
_chemical_formula_sum            'C17 H16 O4'
_chemical_formula_weight         284.30
_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             2023-06-19
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-06-19 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.366(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.1299(4)
_cell_length_b                   14.7848(10)
_cell_length_c                   9.1241(6)
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      26.5440
_cell_measurement_theta_min      2.6220
_cell_volume                     692.00(8)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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    107.79 251.79   0.50    3.00  15.81  -9.84 -59.25    --   288
  2  \w   -100.81  15.69   0.50    3.00    --   -9.84 -59.25  20.08  233
  3  \f    181.44 325.44   0.50    3.00  81.02  -9.84  31.50    --   288
;
_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      -0.0482386000
_diffrn_orient_matrix_UB_12      -0.0447820000
_diffrn_orient_matrix_UB_13      0.0060640000
_diffrn_orient_matrix_UB_21      0.1120012000
_diffrn_orient_matrix_UB_22      -0.0164701000
_diffrn_orient_matrix_UB_23      -0.0364649000
_diffrn_orient_matrix_UB_31      0.0651407000
_diffrn_orient_matrix_UB_32      -0.0048311000
_diffrn_orient_matrix_UB_33      0.0684301000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7550
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.623
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35497
_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            'clear light colourless'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0502P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1073
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2159
_reflns_number_total             2381
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02013d2.cif
_cod_data_source_block           raf_rsr_naph_t_autored
_cod_depositor_comments
'Adding full bibliography for 7159727--7159729.cif.'
_cod_database_code               7159728
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHO
_reflns_odcompleteness_completeness 84.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.70
_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:
 C005(H005), C009(H009), C00B(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00E(H00F), C00F(H00G), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L)
2.d X=CH2 refined with riding coordinates:
 C00D(H00D,H00E)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003)
;
_shelx_res_checksum              30262
_shelx_hkl_checksum              99965
_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 2.433
_oxdiff_exptl_absorpt_empirical_full_min 0.581