Total syntheses of (+)-adunctins C and D: assignment of their absolute configurations.
Xiao, Jian; Zhao, Jun; Wang, Ya-Wen; Luo, Gan; Peng, Yu; Organic & biomolecular chemistry 19 (2021) 9840–9843; doi:10.1039/d1ob02055b

data_7158363
_publ_section_title
;
 Total syntheses of (+)-adunctins C and D: assignment of their absolute
 configurations.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9840
_journal_page_last               9843
_journal_paper_doi               10.1039/d1ob02055b
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H30 O4'
_chemical_formula_sum            'C26 H30 O4'
_chemical_formula_weight         406.50
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-26 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                105.317(4)
_cell_angle_beta                 102.940(4)
_cell_angle_gamma                105.980(4)
_cell_formula_units_Z            2
_cell_length_a                   10.6249(4)
_cell_length_b                   10.6722(5)
_cell_length_c                   11.3614(5)
_cell_measurement_reflns_used    5782
_cell_measurement_temperature    293.60(10)
_cell_measurement_theta_max      69.5590
_cell_measurement_theta_min      6.6370
_cell_volume                     1131.72(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.60(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_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    -36.00  17.00   1.00    1.00    --    0.00 -57.00   0.00   53
  2  \w    -19.00  26.00   1.00    1.00    --    0.00 -38.00  90.00   45
  3  \w      1.00  91.00   1.00    1.00    --   54.00 -99.00   0.00   90
  4  \w     68.00 116.00   1.00    2.00    --  108.00-111.00  60.00   48
  5  \w     47.00 105.00   1.00    2.00    --  108.00 -63.00 -60.00   58
  6  \w     37.00 112.00   1.00    2.00    --  108.00-111.00 -60.00   75
  7  \w     41.00 126.00   1.00    2.00    --  108.00 -50.00  90.00   85
  8  \w     60.00 149.00   1.00    1.00    --   80.00  52.00  11.00   89
  9  \w    124.00 158.00   1.00    2.00    --  108.00  63.00 -30.00   34
 10  \w    122.00 149.00   1.00    2.00    --   92.00  75.00 -98.06   27
 11  \w    118.00 164.00   1.00    2.00    --   96.00  75.00-155.27   46
 12  \w     89.00 138.00   1.00    1.00    --   68.00  74.00-108.12   49
 13  \w     87.00 112.00   1.00    2.00    --  108.00  63.00 -30.00   25
 14  \w     86.00 119.00   1.00    2.00    --  108.00  50.00   0.00   33
 15  \w    118.00 144.00   1.00    2.00    --  100.00  76.00  28.63   26
 16  \w    118.00 159.00   1.00    2.00    --   92.00  73.00  54.42   41
 17  \w    124.00 171.00   1.00    2.00    --  108.00 111.00  60.00   47
 18  \w    100.00 128.00   1.00    1.00    --   60.00  76.00 119.59   28
 19  \w     97.00 128.00   1.00    1.00    --   60.00  74.00 168.66   31
 20  \w     86.00 176.00   1.00    2.00    --  108.00  63.00  90.00   90
 21  \w     87.00 117.00   1.00    1.00    --   60.00  67.00  62.32   30
 22  \w     80.00 132.00   1.00    1.00    --   64.00  68.00  82.39   52
 23  \w     87.00 153.00   1.00    2.00    --  108.00  63.00  60.00   66
 24  \w     88.00 116.00   1.00    2.00    --  108.00  63.00   0.00   28
 25  \w     78.00 157.00   1.00    2.00    --  108.00  77.00 -60.00   79
 26  \w     79.00 174.00   1.00    2.00    --  108.00  77.00-180.00   95
 27  \w     78.00 157.00   1.00    2.00    --  108.00  77.00-150.00   79
 28  \w     78.00 145.00   1.00    2.00    --  108.00  77.00   0.00   67
 29  \w     78.00 147.00   1.00    2.00    --  108.00  77.00 -90.00   69
 30  \w     79.00 170.00   1.00    2.00    --  108.00  77.00-120.00   91
 31  \w     78.00 104.00   1.00    2.00    --  108.00  77.00  60.00   26
 32  \w     80.00 108.00   1.00    2.00    --  108.00  77.00  90.00   28
 33  \w     78.00 170.00   1.00    2.00    --  108.00  77.00 150.00   92
 34  \w     79.00 163.00   1.00    2.00    --  108.00  77.00 120.00   84
 35  \w     71.00  97.00   1.00    2.00    --  100.00  76.00  28.63   26
 36  \w     64.00  90.00   1.00    2.00    --   92.00  73.00  54.42   26
 37  \w     41.00  67.00   1.00    1.00    --   64.00  68.00  82.39   26
 38  \w     45.00  84.00   1.00    1.00    --   68.00  45.00  97.59   39
 39  \w     61.00  87.00   1.00    2.00    --   88.00  71.00 155.17   26
 40  \w     51.00  79.00   1.00    1.00    --   72.00  60.00 171.85   28
 41  \w     32.00  60.00   1.00    1.00    --   60.00  76.00 119.59   28
 42  \w     36.00  62.00   1.00    1.00    --   60.00  67.00  62.32   26
 43  \w     41.00  74.00   1.00    1.00    --   64.00  65.00  22.76   33
 44  \w     43.00 116.00   1.00    1.00    --   72.00  76.00 -40.06   73
 45  \w     64.00  94.00   1.00    2.00    --   84.00  54.00 -99.32   30
 46  \w     68.00  94.00   1.00    2.00    --   96.00  75.00-155.27   26
 47  \w     63.00  90.00   1.00    2.00    --   92.00  75.00 -98.06   27
 48  \w     66.00 143.00   1.00    2.00    --   92.00  70.00-171.30   77
 49  \w     57.00 150.00   1.00    2.00    --  108.00 178.00 -30.00   93
 50  \w     40.00  80.00   1.00    1.00    --   68.00  74.00-108.12   40
 51  \w     33.00 117.00   1.00    1.00    --   60.00  71.00-139.72   84
 52  \w     32.00  65.00   1.00    1.00    --   60.00  75.00 -62.56   33
 53  \w     28.00  58.00   1.00    1.00    --   56.00  76.00-117.87   30
 54  \w     20.00  45.00   1.00    1.00    --   52.00  81.00 -68.18   25
 55  \w     29.00  56.00   1.00    1.00    --   56.00  76.00 -38.95   27
 56  \w     19.00  44.00   1.00    1.00    --   52.00  82.00   6.17   25
 57  \w     11.00  36.00   1.00    1.00    --   44.00  83.00  50.74   25
 58  \w     16.00  45.00   1.00    1.00    --   48.00  82.00  70.63   29
 59  \w     25.00  61.00   1.00    1.00    --   54.00  77.00 150.00   36
 60  \w     34.00  60.00   1.00    1.00    --   60.00  74.00 168.66   26
 61  \w      1.00  26.00   1.00    1.00    --   40.00  93.00 145.98   25
 62  \w    -19.00  69.00   1.00    1.00    --    0.00  57.00 150.00   88
 63  \w    -29.00   7.00   1.00    1.00    --   20.00 111.00 -39.03   36
 64  \w      3.00  30.00   1.00    1.00    --   40.00  89.00 -55.31   27
 65  \w     16.00  41.00   1.00    1.00    --   48.00  80.00-144.78   25
 66  \w    -20.00   5.00   1.00    1.00    --   32.00 116.00-136.38   25
 67  \w    -53.00 -21.00   1.00    1.00    --    0.00 -38.00  90.00   32
 68  \w    -64.00 -38.00   1.00    1.00    --    0.00 -57.00   0.00   26
 69  \w      1.00  94.00   1.00    1.00    --   54.00 -99.00-180.00   93
 70  \w     39.00 126.00   1.00    2.00    --  108.00 -91.00  90.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0443660000
_diffrn_orient_matrix_UB_12      0.1552244000
_diffrn_orient_matrix_UB_13      0.0158515000
_diffrn_orient_matrix_UB_21      -0.1380801000
_diffrn_orient_matrix_UB_22      0.0028626000
_diffrn_orient_matrix_UB_23      0.0198481000
_diffrn_orient_matrix_UB_31      0.0656312000
_diffrn_orient_matrix_UB_32      0.0393041000
_diffrn_orient_matrix_UB_33      0.1461993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16230
_diffrn_reflns_point_group_measured_fraction_full 0.909
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        66.579
_diffrn_reflns_theta_max         66.579
_diffrn_reflns_theta_min         4.569
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       plate
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         7278
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0713
_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^)+(0.1389P)^2^+0.0491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2089
_refine_ls_wR_factor_ref         0.2322
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                5727
_reflns_number_total             7278
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02055b2.cif
_cod_data_source_block           zhuangzhy_1014-1
_cod_depositor_comments
'Adding full bibliography for 7158361--7158363.cif.'
_cod_original_cell_volume        1131.72(9)
_cod_database_code               7158363
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.917
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00L(H00L), C00N(H00N), C00X(H00X), C01F(H01F)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00M(H00F,H00G), C00S(H00H,H00I), C00Y(H00C,H00D), C014(H01A,
 H01B), C015(H01S,H01T), C016(H01U,H01V), C01B(H01X,H01Y), C01E(H01C,H01D),
 C01H(H01E,H01H)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00E), C00J(H00J), C00K(H00K), C00O(H00O), C00R(H00R), C00V(H00V),
 C00W(H00W), C012(H012), C013(H013), C017(H017), C018(H018), C01A(H01W),
 C01C(H01Z), C01G(H01G), C01I(H01), C01K(H01K)
2.d Idealised Me refined as rotating group:
 C00Z(H00M,H00P,H00Q), C010(H01P,H01Q,H01R), C01L(H01I,H01J,H01L), C01N(H01M,
 H01N,H01O), C3(H3A,H3B,H3C), C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O007(H007), O009(H009)
;
_shelx_res_checksum              37474
_olex2_date_sample_data_collection 2020-10-14
_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 2.819
_oxdiff_exptl_absorpt_empirical_full_min 0.343