Genome-Guided Discovery of Highly Oxygenated Aromatic Polyketides, Saccharothrixins D-M, from the Rare Marine Actinomycete <i>Saccharothrix</i> sp. D09.
Shen, Qiyao; Dai, Guangzhi; Li, Aiying; Liu, Yang; Zhong, Guannan; Li, Xiaoju; Ren, Xiangmei; Sui, Haiyan; Fu, Jun; Jiao, Nianzhi; Zhang, Youming; Bian, Xiaoying; Zhou, Haibo; Journal of natural products 84 (2021) 2875–2884; doi:10.1021/acs.jnatprod.1c00617

data_1565516
_publ_section_title
;
 Genome-Guided Discovery of Highly Oxygenated Aromatic Polyketides,
 Saccharothrixins D-M, from the Rare Marine Actinomycete
 <i>Saccharothrix</i> sp. D09.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2875
_journal_page_last               2884
_journal_paper_doi               10.1021/acs.jnatprod.1c00617
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 O6, 2(C H4 O)'
_chemical_formula_sum            'C22 H28 O8'
_chemical_formula_weight         420.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.1467(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.50545(6)
_cell_length_b                   7.48037(5)
_cell_length_c                   18.43974(14)
_cell_measurement_reflns_used    31696
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.2540
_cell_measurement_theta_min      2.3850
_cell_volume                     1034.546(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.977
_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    -74.00  27.00   0.50    0.05    --  -45.95  88.00 -20.00  202
  2  \w    -26.00  74.00   0.50    0.05    --   45.95 -88.00-137.00  200
  3  \w   -130.00 -29.00   0.50    0.05    -- -102.00  88.00 -20.00  202
  4  \w   -175.00 -80.00   0.50    0.05    -- -102.00 -88.00-137.00  190
  5  \w     31.00 132.00   0.50    0.05    --  103.99 -88.00-137.00  202
  6  \w     84.00 177.00   0.50    0.05    --  103.99  88.00 -20.00  186
  7  \w   -118.00 -31.00   0.50    0.05    --  -45.95 -57.00 150.00  174
  8  \w   -119.00 -74.00   0.50    0.05    --  -45.95-125.00   0.00   90
  9  \w     31.00 118.00   0.50    0.05    --   45.95  57.00   0.00  174
 10  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -60.00  192
 11  \w   -115.00 -27.00   0.50    0.05    -- -102.00  30.00   0.00  176
 12  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 -90.00  192
 13  \w   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00 150.00  170
 14  \w   -175.00 -89.00   0.50    0.05    -- -102.00 -30.00 120.00  172
 15  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00 -60.00  180
 16  \w   -175.00 -88.00   0.50    0.05    -- -102.00 -15.00 -90.00  174
 17  \w   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00  90.00  170
 18  \w     31.00 106.00   0.50    0.05    --  103.99 -94.00 -60.00  150
 19  \w     31.00 106.00   0.50    0.05    --  103.99 -94.00  60.00  150
 20  \w     91.00 178.00   0.50    0.05    --  103.99  30.00  60.00  174
 21  \w     23.00 119.00   0.50    0.05    --   45.95  77.00-120.00  192
 22  \w     23.00 119.00   0.50    0.05    --   45.95  77.00  60.00  192
 23  \w     23.00 119.00   0.50    0.05    --   45.95  77.00 150.00  192
 24  \w     18.00  94.00   0.50    0.05    --   45.95-125.00-150.00  152
 25  \w     31.00 118.00   0.50    0.05    --   45.95  57.00-120.00  174
 26  \w     31.00 118.00   0.50    0.05    --   45.95  57.00 -30.00  174
 27  \w   -112.00 -29.00   0.50    0.05    -- -102.00 125.00  90.00  166
 28  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00-180.00  180
 29  \w   -174.00 -89.00   0.50    0.05    -- -102.00 -45.00  60.00  170
 30  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 150.00  192
 31  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00-120.00  192
 32  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00 120.00  192
 33  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00  60.00  192
 34  \w   -125.00 -29.00   0.50    0.05    -- -102.00  77.00-180.00  192
 35  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00  90.00  180
 36  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00-150.00  180
 37  \w     81.00 177.00   0.50    0.05    --  103.99  77.00 -30.00  192
 38  \w     81.00 177.00   0.50    0.05    --  103.99  77.00 -60.00  192
 39  \w   -119.00 -33.00   0.50    0.05    --  -45.95 -37.00 -90.00  172
 40  \w     23.00 119.00   0.50    0.05    --   45.95  77.00-150.00  192
 41  \w     23.00 119.00   0.50    0.05    --   45.95  77.00   0.00  192
 42  \w     23.00 119.00   0.50    0.05    --   45.95  77.00 -60.00  192
 43  \w     31.00 118.00   0.50    0.05    --   45.95  57.00 150.00  174
 44  \w     23.00 119.00   0.50    0.05    --   45.95  77.00  90.00  192
 45  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00  30.00  192
 46  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00 150.00  180
 47  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00  30.00  180
 48  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00-120.00  180
 49  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00 -90.00  180
 50  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00-150.00  192
 51  \w   -175.00 -79.00   0.50    0.05    -- -102.00 -77.00-180.00  192
 52  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00 120.00  180
 53  \w   -175.00 -85.00   0.50    0.05    -- -102.00 -61.00  60.00  180
 54  \w     88.00 177.00   0.50    0.05    --  103.99  61.00 -30.00  178
 55  \w     81.00 177.00   0.50    0.05    --  103.99  77.00  30.00  192
 56  \w     88.00 177.00   0.50    0.05    --  103.99  61.00 -60.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1519757000
_diffrn_orient_matrix_UB_12      0.0353527000
_diffrn_orient_matrix_UB_13      -0.0566561000
_diffrn_orient_matrix_UB_21      0.0353047000
_diffrn_orient_matrix_UB_22      -0.1825664000
_diffrn_orient_matrix_UB_23      -0.0353574000
_diffrn_orient_matrix_UB_31      -0.1336088000
_diffrn_orient_matrix_UB_32      -0.0885425000
_diffrn_orient_matrix_UB_33      0.0502801000
_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  0.0389
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            39359
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.480
_diffrn_reflns_theta_min         4.800
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
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    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4205
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0948P)^2^+0.2796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4069
_reflns_number_total             4205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00617_si_003.cif
_cod_data_source_block           b_1_3
_cod_original_cell_volume        1034.545(14)
_cod_database_code               1565516
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c1 h1 o1'
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.950
_reflns_odcompleteness_completeness 100.00
_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:
 C7(H7), C10(H10), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C6(H6), C12(H12), C13(H13), C17(H17), C19(H19)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O5(H5), O7(H7A), O8(H8)
;
_shelx_res_checksum              54805
_shelx_hkl_checksum              43663
_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 1.373
_oxdiff_exptl_absorpt_empirical_full_min 0.742