<i>S</i>-Bridged Thioether and Structure-Diversified Angucyclinone Derivatives from the South China Sea-Derived <i>Micromonospora echinospora</i> SCSIO 04089.
Fang, Zhuangjie; Jiang, Xiaodong; Zhang, Qingbo; Zhang, Liping; Zhang, Wenjun; Yang, Chunfang; Zhang, Haibo; Zhu, Yiguang; Zhang, Changsheng; Journal of natural products  (2020) –; doi:10.1021/acs.jnatprod.0c00719

data_1559201
_publ_section_title
;
 <i>S</i>-Bridged Thioether and Structure-Diversified Angucyclinone
 Derivatives from the South China Sea-Derived <i>Micromonospora
 echinospora</i> SCSIO 04089.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.0c00719
_journal_year                    2020
_chemical_formula_moiety         'C18 H14 O5'
_chemical_formula_sum            'C18 H14 O5'
_chemical_formula_weight         310.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                80.099(3)
_cell_angle_beta                 84.102(2)
_cell_angle_gamma                82.308(3)
_cell_formula_units_Z            2
_cell_length_a                   5.0126(2)
_cell_length_b                   9.6467(4)
_cell_length_c                   14.7488(3)
_cell_measurement_reflns_used    3527
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      73.4260
_cell_measurement_theta_min      5.1640
_cell_volume                     693.91(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.959
_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    -40.00  15.00   0.50    1.50    --    0.00 -55.00-138.00  110
  2  \w     20.00  49.00   0.50    1.50    --    0.00  55.00   4.00   58
  3  \w     35.00  76.00   0.50    9.00    --   94.60 -55.00-138.00   82
  4  \w     72.00 169.00   0.50    9.00    --   94.60  55.00   4.00  194
  5  \w    -33.00  15.00   0.50    1.50    --    0.00 -82.00 -30.00   96
  6  \w    -26.00  30.00   0.50    1.50    --    0.00 -82.00   0.00  112
  7  \w    -30.00  31.00   0.50    1.50    --    0.00 -82.00-180.00  122
  8  \w     78.00 111.00   0.50    9.00    --   94.60 -30.00  60.00   66
  9  \w      5.00 123.00   0.50    9.00    --   94.60 -77.00-150.00  236
 10  \w     11.00 119.00   0.50    9.00    --   94.60 -82.00  60.00  216
 11  \w     81.00 107.00   0.50    9.00    --   94.60 -82.00 -60.00   52
 12  \w    120.00 167.00   0.50    9.00    --   94.60  15.00 150.00   94
 13  \w     71.00 173.00   0.50    9.00    --   94.60  61.00  60.00  204
 14  \w     87.00 178.00   0.50    9.00    --   94.60  82.00 -90.00  182
 15  \w     87.00 113.00   0.50    9.00    --   94.60  45.00  30.00   52
 16  \w    142.00 168.00   0.50    9.00    --   94.60  45.00  30.00   52
 17  \w     47.00 126.00   0.50    9.00    --   94.60 -82.00-180.00  158
 18  \w     11.00 104.00   0.50    9.00    --   94.60 -82.00   0.00  186
 19  \w     93.00 119.00   0.50    9.00    --   94.60  15.00 150.00   52
 20  \w     36.00  61.00   0.50    9.00    --   94.60 -82.00 -60.00   50
 21  \w     32.00  58.00   0.50    9.00    --   94.60 -82.00-120.00   52
 22  \w     89.00 114.00   0.50    9.00    --   94.60 -82.00-120.00   50
 23  \w      6.00  59.00   0.50    9.00    --   94.60 -30.00  60.00  106
 24  \w     77.00 102.00   0.50    9.00    --   94.60 -82.00 -90.00   50
 25  \w     23.00  97.00   0.50    9.00    --   94.60 -61.00  60.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0269712000
_diffrn_orient_matrix_UB_12      -0.1489813000
_diffrn_orient_matrix_UB_13      -0.0268524000
_diffrn_orient_matrix_UB_21      0.2257228000
_diffrn_orient_matrix_UB_22      -0.0502677000
_diffrn_orient_matrix_UB_23      0.0657730000
_diffrn_orient_matrix_UB_31      -0.2124777000
_diffrn_orient_matrix_UB_32      -0.0439635000
_diffrn_orient_matrix_UB_33      0.0791913000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7210
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.744
_diffrn_reflns_theta_min         4.686
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0595
_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^)+(0.1035P)^2^+0.1921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1711
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2287
_reflns_number_total             2691
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00719_si_007.cif
_cod_data_source_block           fangzhuangjie_29t-4_collect
_cod_database_code               1559201
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C36 H28 O10 '
_reflns_odcompleteness_completeness 99.15
_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 Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C13(H13), C12(H12)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O15(H15)
;
_shelx_res_checksum              65328
_shelx_hkl_checksum              81579
_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 2.252
_oxdiff_exptl_absorpt_empirical_full_min 0.392