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_7158362
_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_formula_moiety         'C26 H28 O4'
_chemical_formula_sum            'C26 H28 O4'
_chemical_formula_weight         404.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-08-17 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.257(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.8005(6)
_cell_length_b                   5.76195(16)
_cell_length_c                   37.1847(13)
_cell_measurement_reflns_used    3211
_cell_measurement_temperature    293.32(10)
_cell_measurement_theta_max      69.5910
_cell_measurement_theta_min      4.8010
_cell_volume                     4410.4(2)
_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 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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.32(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0367
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     41.00  98.00   1.00    3.00    --   54.00  57.00   0.00   57
  2  \w    131.00 157.00   1.00   16.00    --  108.00 111.00  90.00   26
  3  \w     97.00 178.00   1.00   16.00    --  108.00  50.00  60.00   81
  4  \w    116.00 168.00   1.00   16.00    --  108.00 111.00 -60.00   52
  5  \w     74.00 178.00   1.00   16.00    --  108.00  25.00   0.00  104
  6  \w     52.00 111.00   1.00    3.00    --   54.00-125.00 -30.00   59
  7  \w     43.00  79.00   1.00   16.00    --  108.00 -50.00  90.00   36
  8  \w     37.00 111.00   1.00   16.00    --  108.00-111.00-120.00   74
  9  \w     43.00 129.00   1.00   16.00    --  108.00 -50.00-180.00   86
 10  \w     47.00 111.00   1.00    3.00    --   54.00  57.00-150.00   64
 11  \w     22.00  68.00   1.00    1.00    --    0.00  77.00-120.00   46
 12  \w     -5.00  65.00   1.00    1.00    --    0.00  57.00-180.00   70
 13  \w     -9.00  77.00   1.00    3.00    --   54.00 -38.00-150.00   86
;
_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      -0.0158751000
_diffrn_orient_matrix_UB_12      0.0544275000
_diffrn_orient_matrix_UB_13      -0.0408875000
_diffrn_orient_matrix_UB_21      0.0725947000
_diffrn_orient_matrix_UB_22      -0.0203390000
_diffrn_orient_matrix_UB_23      -0.0037460000
_diffrn_orient_matrix_UB_31      -0.0089723000
_diffrn_orient_matrix_UB_32      -0.2609166000
_diffrn_orient_matrix_UB_33      -0.0082275000
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            6987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.549
_diffrn_reflns_theta_max         66.549
_diffrn_reflns_theta_min         4.296
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89711
_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    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0910P)^2^+1.8024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1664
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3054
_reflns_number_total             3866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02055b2.cif
_cod_data_source_block           zhaungzhy_0525
_cod_depositor_comments
'Adding full bibliography for 7158361--7158363.cif.'
_cod_original_cell_volume        4410.5(2)
_cod_database_code               7158362
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.909
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H19,H19A,H19B} of C19, {H24,H24A,H24B} of C24, All C(H,H)
  groups
 At 1.5 times of:
  All O(H) groups, {H23A,H23B,H23C} of C23, {H31A,H31B,H31C} of C31
2. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H19(0.5) H19A(0.5) H19B(0.5) H24(0.5) H24A(0.5) H24B(0.5) H25(0.5)
 H25A(0.5) C26(0.5) H26(0.5) C2(0.55) H2A(0.55) H2B(0.55) C1(0.45) H1A(0.45)
 H1B(0.45) C27(0.5) H27(0.5) C4(0.5) H4A(0.5) H4B(0.5) C3(0.5) H3A(0.5) H3B(0.5)
4.a Ternary CH refined with riding coordinates:
 C25(H25), C25(H25A)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C19(H19A,H19B), C21(H21A,H21B), C24(H24A,
 H24B), C4(H4A,H4B), C3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22),
 C24(H24), C26(H26), C27(H27)
4.d X=CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B)
4.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C31(H31A,H31B,H31C)
4.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              97433
_olex2_date_sample_data_collection 2020-05-25
_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.390