Ten-step asymmetric total syntheses of potent antibiotics anthracimycin and anthracimycin B.
Tian, Peilin; Ye, Wenkang; Zhang, Xiayan; Tong, Yi; Qian, Pei-Yuan; Tong, Rongbiao; Chemical science 13 (2022) 12776–12781; doi:10.1039/d2sc05049h

data_1567787
_publ_section_title
;
 Ten-step asymmetric total syntheses of potent antibiotics anthracimycin
 and anthracimycin B.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              12776
_journal_page_last               12781
_journal_paper_doi               10.1039/d2sc05049h
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C25 H32 O4'
_chemical_formula_sum            'C25 H32 O4'
_chemical_formula_weight         396.50
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-06-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-04 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5419(2)
_cell_length_b                   15.3789(5)
_cell_length_c                   25.7913(8)
_cell_measurement_reflns_used    4474
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      75.5580
_cell_measurement_theta_min      4.4300
_cell_volume                     2198.15(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.870
_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    127.00 132.00   0.50    1.00    --  107.15  70.00   0.00   10
  2  \w    127.00 132.00   0.50    1.00    --  107.15  70.00  90.00   10
  3  \w     77.00  82.00   0.50    1.00    --  107.15 -70.00  90.00   10
  4  \w     28.00  33.00   0.50    0.25    --   46.28 -70.00  90.00   10
  5  \w    -24.00 -19.00   0.50    0.25    --  -46.28  70.00  90.00   10
  6  \w     24.00  29.00   0.50    0.25    --  -46.28  30.00   0.00   10
  7  \w   -108.00 -73.00   0.50    0.25    --  -45.77-159.00 -88.00   70
  8  \w   -125.00 -84.00   0.50    1.00    --  -97.00 -25.00 -87.00   82
  9  \w    -88.00 -36.00   0.50    1.00    --  -97.00 101.00-107.00  104
 10  \w     54.00 123.00   0.50    1.00    --  105.42-159.00 -88.00  138
 11  \w    -29.00   8.00   0.50    0.25    --   45.77 -19.00 150.00   74
 12  \w     -8.00  30.00   0.50    0.25    --   45.77 -37.00-180.00   76
 13  \w     -8.00  24.00   0.50    0.25    --   45.77 -19.00-150.00   64
 14  \w    -54.00 -27.00   0.50    1.00    --  -97.00  57.00-180.00   54
 15  \w    -69.00 -25.00   0.50    1.00    --  -97.00  57.00  30.00   88
 16  \w    -69.00 -26.00   0.50    1.00    --  -97.00  57.00 -90.00   86
 17  \w    -62.00 -26.00   0.50    1.00    --  -97.00  57.00  60.00   72
 18  \w     33.00  63.00   0.50    1.00    --  105.42 -57.00-150.00   60
 19  \w     34.00  62.00   0.50    1.00    --  105.42 -57.00 -60.00   56
 20  \w   -112.00 -87.00   0.50    0.25    --  -45.77-159.00 -88.00   50
 21  \w   -112.00 -87.00   0.50    0.25    --  -45.77-159.00 -88.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0726170000
_diffrn_orient_matrix_UB_12      0.0336978000
_diffrn_orient_matrix_UB_13      -0.0540343000
_diffrn_orient_matrix_UB_21      0.2655149000
_diffrn_orient_matrix_UB_22      -0.0047767000
_diffrn_orient_matrix_UB_23      -0.0175766000
_diffrn_orient_matrix_UB_31      -0.0394282000
_diffrn_orient_matrix_UB_32      -0.0941778000
_diffrn_orient_matrix_UB_33      -0.0184227000
_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  0.0906
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7767
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.588
_diffrn_reflns_theta_min         4.475
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.198
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 1062 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0709
_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^)+(0.1263P)^2^+0.6553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.1917
_reflns_Friedel_coverage         0.588
_reflns_Friedel_fraction_full    0.815
_reflns_Friedel_fraction_max     0.709
_reflns_number_gt                3319
_reflns_number_total             3739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05049h2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 1567786--1567787.cif.'
_cod_database_code               1567787
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C25H32O4
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.928
_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
2.a Ternary CH refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00I(H00I),
 C00N(H00P)
2.b Secondary CH2 refined with riding coordinates:
 C00K(H00J,H00K), C00O(H00Q,H00R)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00C(H00C), C00G(H00G), C00H(H00H), C00L(H00L),
 C00P(H00S), C00R(H00W)
2.d Idealised Me refined as rotating group:
 C00M(H00M,H00N,H00O), C00Q(H00T,H00U,H00V), C00S(H00X,H00Y,H), C00T(H00Z,HA,HB)
;
_shelx_res_checksum              80011
_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 4.120
_oxdiff_exptl_absorpt_empirical_full_min 0.225