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_7159727
_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         'C13 H18 O4'
_chemical_formula_sum            'C13 H18 O4'
_chemical_formula_weight         238.27
_chemical_melting_point          153.0(10)
_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             2023-01-05
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2023-01-13 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.257(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5355(3)
_cell_length_b                   7.5626(2)
_cell_length_c                   11.2958(3)
_cell_measurement_reflns_used    4214
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.3300
_cell_measurement_theta_min      1.8610
_cell_volume                     626.57(4)
_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_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   -100.81  15.69   0.50    4.00    --   -9.84 -59.25-123.92  233
  2  \f    -90.56  13.44   0.50    4.00  81.02  -9.84  31.50    --   208
  3  \w    -65.46   0.04   0.50    4.00    --  -19.34  94.56   1.16  131
  4  \w   -100.81  15.69   0.50    4.00    --   -9.84 -59.25  92.08  233
  5  \w   -100.81  15.69   0.50    4.00    --   -9.84 -59.25 164.08  233
  6  \f    166.27 350.27   0.50    4.00   6.61  -9.84 -31.50    --   368
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0070589000
_diffrn_orient_matrix_UB_12      -0.0199144000
_diffrn_orient_matrix_UB_13      -0.0601098000
_diffrn_orient_matrix_UB_21      0.0884919000
_diffrn_orient_matrix_UB_22      -0.0350976000
_diffrn_orient_matrix_UB_23      0.0229587000
_diffrn_orient_matrix_UB_31      -0.0383565000
_diffrn_orient_matrix_UB_32      -0.0846609000
_diffrn_orient_matrix_UB_33      0.0046372000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1451
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12140
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         1.852
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61679
_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            'Yellow Solid'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.089
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0825P)^2^+0.0318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1341
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2051
_reflns_number_total             2191
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02013d2.cif
_cod_data_source_block           raf_rsr_163_a_autored
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '152-154' was changed to
'153.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159727--7159729.cif.
;
_cod_database_code               7159727
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 78.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.72
_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.a Ternary CH refined with riding coordinates:
 C005(H005), C008(H008), C00D(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00C,H00D), C00E(H00F,H00G), C00G(H00K,H00L), C00H(H00M,H00N)
2.c X=CH2 refined with riding coordinates:
 C009(H00A,H00B)
2.d Idealised Me refined as rotating group:
 C00F(H00H,H00I,H00J)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002)
;
_shelx_res_checksum              99123
_shelx_hkl_checksum              94926
_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 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.647