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_1567786
_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 ad
_chemical_formula_moiety         'C15 H20 O2'
_chemical_formula_sum            'C15 H20 O2'
_chemical_formula_weight         232.31
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-06-17
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2021.06.11 svn.re2ff6fc5 for OlexSys, GUI svn.r6348)
;
_audit_update_record
;
2022-05-27 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                   5.60939(10)
_cell_length_b                   10.26643(19)
_cell_length_c                   22.2551(4)
_cell_measurement_reflns_used    6330
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      76.4190
_cell_measurement_theta_min      3.9560
_cell_volume                     1281.64(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_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     36.00 109.00   1.00    5.00    --  113.00-111.00  60.00   73
  2  \w    -70.00  22.00   1.00    2.00    --  -39.95  57.00   0.00   92
  3  \w   -112.00 -14.00   1.00    2.00    --  -39.95 -37.00-180.00   98
  4  \w     43.00  97.00   1.00    2.00    --   39.95-125.00 150.00   54
  5  \w     10.00 110.00   1.00    2.00    --   39.95  57.00 120.00  100
  6  \w     83.00 178.00   1.00    5.00    --  113.00  30.00 -60.00   95
  7  \w     43.00 144.00   1.00    5.00    --  113.00 -30.00-120.00  101
  8  \w     83.00 114.00   1.00    5.00    --  113.00  61.00-120.00   31
  9  \w    120.00 175.00   1.00    5.00    --  113.00  77.00 -30.00   55
 10  \w    139.00 178.00   1.00    5.00    --  113.00  61.00-120.00   39
 11  \w    103.00 178.00   1.00    5.00    --  113.00  77.00-150.00   75
 12  \w     93.00 141.00   1.00    5.00    --  113.00 -77.00 120.00   48
 13  \w     52.00 135.00   1.00    5.00    --  113.00 -77.00-120.00   83
 14  \w     42.00 109.00   1.00    5.00    --  113.00-111.00-180.00   67
 15  \w     34.00  62.00   1.00    5.00    --  113.00 -77.00 120.00   28
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0018372000
_diffrn_orient_matrix_UB_12      -0.0857354000
_diffrn_orient_matrix_UB_13      0.0568067000
_diffrn_orient_matrix_UB_21      0.1467134000
_diffrn_orient_matrix_UB_22      -0.1038423000
_diffrn_orient_matrix_UB_23      -0.0336409000
_diffrn_orient_matrix_UB_31      0.2321845000
_diffrn_orient_matrix_UB_32      0.0662240000
_diffrn_orient_matrix_UB_33      0.0207843000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7631
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.640
_diffrn_reflns_theta_min         3.973
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1054 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0463P)^2^+0.4110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                2612
_reflns_number_total             2639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05049h2.cif
_cod_data_source_block           ptian3cult
_cod_depositor_comments
'Adding full bibliography for 1567786--1567787.cif.'
_cod_database_code               1567786
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C2(H2), C3(H3), C8(H8), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              84154
_olex2_date_sample_data_collection 2021-06-15
_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 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.399