<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_1559197
_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         'C H Cl3, 2(C19 H13 N O4)'
_chemical_formula_sum            'C39 H27 Cl3 N2 O8'
_chemical_formula_weight         757.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-04-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.214(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5364(7)
_cell_length_b                   25.2316(6)
_cell_length_c                   7.0100(2)
_cell_measurement_reflns_used    6521
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4490
_cell_measurement_theta_min      5.7510
_cell_volume                     3286.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_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     -2.00  31.00   0.50    1.00    --    0.00 -82.00 -60.00   66
  2  \w    -13.00  28.00   0.50    1.00    --    0.00 -82.00-150.00   82
  3  \w    -40.00 -15.00   0.50    1.00    --    0.00 -77.00 -90.00   50
  4  \w    -28.00  21.00   0.50    1.00    --    0.00 -82.00 120.00   98
  5  \w     17.00 117.00   0.50    3.00    --   94.60 -61.00   0.00  200
  6  \w     87.00 184.00   0.50    3.00    --   94.60  82.00 120.00  194
  7  \w     89.00 177.00   0.50    3.00    --   94.60  82.00-120.00  176
  8  \w     71.00 117.00   0.50    3.00    --   94.60 -61.00 150.00   92
  9  \w     27.00  53.00   0.50    3.00    --   94.60 -45.00  90.00   52
 10  \w     65.00 114.00   0.50    3.00    --   94.60 -45.00  90.00   98
 11  \w     76.00 102.00   0.50    3.00    --   94.60 -77.00 -30.00   52
 12  \w     39.00  88.00   0.50    3.00    --   94.60 -45.00   0.00   98
 13  \w     89.00 167.00   0.50    3.00    --   94.60  30.00-150.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0700627000
_diffrn_orient_matrix_UB_12      0.0319569000
_diffrn_orient_matrix_UB_13      0.1108404000
_diffrn_orient_matrix_UB_21      -0.0425745000
_diffrn_orient_matrix_UB_22      0.0451686000
_diffrn_orient_matrix_UB_23      0.0422299000
_diffrn_orient_matrix_UB_31      0.0124043000
_diffrn_orient_matrix_UB_32      -0.0258492000
_diffrn_orient_matrix_UB_33      0.2120423000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8617
_diffrn_reflns_point_group_measured_fraction_full 0.638
_diffrn_reflns_point_group_measured_fraction_max 0.614
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.701
_diffrn_reflns_theta_min         3.503
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       needle
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.023(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         4078
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0514
_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^)+(0.1110P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.259
_reflns_Friedel_fraction_full    0.276
_reflns_Friedel_fraction_max     0.253
_reflns_number_gt                3934
_reflns_number_total             4078
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c00719_si_003.cif
_cod_data_source_block           fangzhuangjie_29t-5_collect
_cod_original_cell_volume        3286.27(19)
_cod_database_code               1559197
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C152 H100 Cl12 O44 '
_shelx_estimated_absorpt_t_max   0.750
_shelx_estimated_absorpt_t_min   0.375
_reflns_odcompleteness_completeness 99.97
_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. Restrained distances
 Cl-C01G
 1.75 with sigma of 0.02
 Cl1-C01G
 1.75 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl02) = Uanis(Cl)
Uanis(Cl03) = Uanis(Cl1)
4. Others
 Sof(H01N)=Sof(Cl)=Sof(Cl1)=1-FVAR(1)
 Sof(Cl02)=Sof(Cl03)=Sof(H01M)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C01G(H01M), C01G(H01N)
5.b Secondary CH2 refined with riding coordinates:
 C01B(H01B,H01C), C01D(H01H,H01I)
5.c Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00W(H00W), C00Y(H00Y), C010(H010), C011(H011), C014(H014),
 C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01A), C01C(H01D)
5.d Idealised Me refined as rotating group:
 C01E(H01E,H01F,H01G), C01F(H01J,H01K,H01L)
5.e Idealised tetrahedral OH refined as rotating group:
 O004(H004), O008(H008), O00A(H00A), O00B(H00B)
;
_shelx_res_checksum              9194
_shelx_hkl_checksum              88038
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.112
_oxdiff_exptl_absorpt_empirical_full_min 0.424