Stereoselective synthesis of an advanced <i>trans</i>-decalin intermediate towards the total synthesis of anthracimycin.
Jeanmard, Laksamee; Lodovici, Giacomo; George, Ian; Bray, Joshua T. W.; Whitwood, Adrian C.; Thomas, Gavin H.; Fairlamb, Ian J. S.; Unsworth, William P.; Clarke, Paul A.; Chemical communications (Cambridge, England) 60 (2024) 5699–5702; doi:10.1039/d4cc01738b

data_7133013
_publ_section_title
;
 Stereoselective synthesis of an advanced <i>trans</i>-decalin
 intermediate towards the total synthesis of anthracimycin.
;
_journal_issue                   44
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5699
_journal_page_last               5702
_journal_paper_doi               10.1039/d4cc01738b
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H22 O5'
_chemical_formula_sum            'C17 H22 O5'
_chemical_formula_weight         306.34
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-21
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-03-20 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.18006(14)
_cell_length_b                   12.9367(2)
_cell_length_c                   17.2317(3)
_cell_measurement_reflns_used    3866
_cell_measurement_temperature    109.95(10)
_cell_measurement_theta_max      70.4050
_cell_measurement_theta_min      6.6670
_cell_volume                     1600.59(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     37.00  65.00   1.00    1.00    --    0.00  57.00 -90.00   28
  2  \w    -22.00  18.00   1.00    1.00    --    0.00  77.00-180.00   40
  3  \w    -16.00  17.00   1.00    1.00    --    0.00  57.00 -90.00   33
  4  \w     79.00 121.00   1.00    1.00    --   54.00-172.00 -73.00   42
  5  \w    -14.00  62.00   1.00    1.00    --   54.00 -57.00 -90.00   76
  6  \w    -15.00  48.00   1.00    1.00    --   54.00 -57.00   0.00   63
  7  \w     37.00 123.00   1.00    1.00    --   54.00  57.00 150.00   86
  8  \w     87.00 113.00   1.00    1.00    --  108.00-131.00 167.00   26
  9  \w    111.00 136.00   1.00    1.00    --  108.00  77.00 150.00   25
 10  \w     37.00  65.00   1.00    1.00    --  108.00-131.00 167.00   28
 11  \w     36.00 104.00   1.00    1.00    --  108.00 -38.00  90.00   68
 12  \w     51.00 107.00   1.00    1.00    --  108.00 -91.00 150.00   56
 13  \w     56.00 124.00   1.00    1.00    --  108.00 -38.00 -30.00   68
 14  \w     58.00 106.00   1.00    1.00    --  108.00 -91.00-120.00   48
 15  \w     42.00 159.00   1.00    1.00    --  108.00  12.00 -60.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1978297000
_diffrn_orient_matrix_UB_12      0.0449453000
_diffrn_orient_matrix_UB_13      -0.0080372000
_diffrn_orient_matrix_UB_21      -0.0829038000
_diffrn_orient_matrix_UB_22      -0.1085111000
_diffrn_orient_matrix_UB_23      0.0127457000
_diffrn_orient_matrix_UB_31      -0.0060765000
_diffrn_orient_matrix_UB_32      0.0195987000
_diffrn_orient_matrix_UB_33      0.0881214000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5384
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.986
_diffrn_reflns_theta_max         66.986
_diffrn_reflns_theta_min         4.273
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.107a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_recrystallization_method
'crystallisation from diethyl ether and chloroform'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1089 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_coef       0.0036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0267
_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^)+(0.0306P)^2^+0.1046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0646
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2692
_reflns_number_total             2860
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01738b2.cif
_cod_data_source_block           pac21002
_cod_depositor_comments
'Adding full bibliography for 7133012--7133013.cif.'
_cod_database_code               7133013
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H22 O5'
_chemical_oxdiff_usercomment     'Laksamee Jeanmard LJG-4-45-1'
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.838
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
;
_shelx_res_checksum              3880
_shelx_hkl_checksum              89692
_olex2_date_sample_data_collection 2021-05-20
_olex2_date_sample_submission    2021-05-18
_olex2_exptl_crystal_mounting_method 'oil on 100 micrometre micromount'
_olex2_submission_original_sample_id LJG-4-45-1
_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 1.231
_oxdiff_exptl_absorpt_empirical_full_min 0.811