<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_1559199
_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_absolute_configuration ad
_chemical_formula_moiety         '2(C20 H18 O7 S)'
_chemical_formula_sum            'C40 H36 O14 S2'
_chemical_formula_weight         804.81
_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     dual
_audit_creation_date             2020-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.05620(10)
_cell_length_b                   20.57850(10)
_cell_length_c                   24.1665(3)
_cell_measurement_reflns_used    19528
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.0240
_cell_measurement_theta_min      3.6870
_cell_volume                     3509.12(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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    -89.00  17.00   0.50    0.50    --    0.00 -38.00  90.00  212
  2  \w    -33.00  31.00   0.50    0.50    --    0.00 -82.00 -60.00  128
  3  \w    -46.00  29.00   0.50    0.50    --    0.00 -77.00  90.00  150
  4  \w     17.00 130.00   0.50    0.50    --  106.20 -61.00-180.00  226
  5  \w     17.00 130.00   0.50    0.50    --  106.20 -15.00-180.00  226
  6  \w     17.00 136.00   0.50    0.50    --  106.20 -77.00-180.00  238
  7  \w     17.00 123.00   0.50    0.50    --  106.20 -30.00 -90.00  212
  8  \w     89.00 196.00   0.50    0.50    --  106.20  40.00 159.42  214
  9  \w     17.00 126.00   0.50    0.50    --  106.20 -45.00 -90.00  218
 10  \w     17.00 123.00   0.50    0.50    --  106.20 -30.00 150.00  212
 11  \w    -33.00  31.00   0.50    0.50    --    0.00 -82.00 150.00  128
 12  \w    -46.00  29.00   0.50    0.50    --    0.00 -77.00-150.00  150
 13  \w    -33.00  31.00   0.50    0.50    --    0.00 -82.00   0.00  128
 14  \w     83.00 123.00   0.50    0.50    --  106.20  15.00  30.00   80
 15  \w     80.00 196.00   0.50    0.50    --  106.20  77.00-150.00  232
 16  \w     83.00 196.00   0.50    0.50    --  106.20  15.00 -60.00  226
;
_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      -0.1446514000
_diffrn_orient_matrix_UB_12      0.0524357000
_diffrn_orient_matrix_UB_13      -0.0168669000
_diffrn_orient_matrix_UB_21      -0.1391135000
_diffrn_orient_matrix_UB_22      -0.0533961000
_diffrn_orient_matrix_UB_23      -0.0186387000
_diffrn_orient_matrix_UB_31      -0.0858818000
_diffrn_orient_matrix_UB_32      -0.0018901000
_diffrn_orient_matrix_UB_33      0.0585953000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            35646
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.341
_diffrn_reflns_theta_min         2.820
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.031
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 2893 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         7494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+2.7002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                7090
_reflns_number_total             7494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00719_si_002.cif
_cod_data_source_block           fzj_5d-1-1
_cod_database_code               1559199
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.95
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C01F-C01K \\sim C01L-C01K
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C01K) = Uanis(C01L)
4. Others
 Sof(H01E)=Sof(H01F)=Sof(C01L)=Sof(H01J)=Sof(H01K)=Sof(H01L)=1-FVAR(1)
 Sof(H01C)=Sof(H01D)=Sof(C01K)=Sof(H01G)=Sof(H01H)=Sof(H01I)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C00K(H00B,H00C), C00Y(H00D,H00E), C011(H01M,H01N), C018(H01O,H01P), C019(H01Q,
 H01R), C01A(H01S,H01T), C01D(H01A,H01B), C01F(H01C,H01D), C01F(H01E,H01F)
5.b Aromatic/amide H refined with riding coordinates:
 C00S(H00S), C00U(H00U), C010(H010), C01H(H01X), C01I(H01Y), C01J(H01Z)
5.c Idealised Me refined as rotating group:
 C01G(H01U,H01V,H01W), C01K(H01G,H01H,H01I), C01L(H01J,H01K,H01L)
5.d Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004), O007(H007), O009(H009), O00A(H00A), O00B(H00F),
 O00C(H00G), O00G(H00H)
;
_shelx_res_checksum              45046
_shelx_hkl_checksum              17023
_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 1.286
_oxdiff_exptl_absorpt_empirical_full_min 0.843