Decalin-Containing Tetramic Acids and 4-Hydroxy-2-pyridones with Antimicrobial and Cytotoxic Activity from the Fungus Coniochaeta cephalothecoides Collected in Tibetan Plateau (Medog).
Han, Junjie; Liu, Congcong; Li, Li; Zhou, Hui; Liu, Li; Bao, Li; Chen, Qian; Song, Fuhang; Zhang, Lixin; Li, Erwei; Liu, Ling; Pei, Yunfei; Jin, Cheng; Xue, Yanfen; Yin, Wenbing; Ma, Yanhe; Liu, Hongwei; The Journal of organic chemistry 82 (2017) 11474–11486; doi:10.1021/acs.joc.7b02010

data_4033021
_publ_section_title
;
 Decalin-Containing Tetramic Acids and 4-Hydroxy-2-pyridones with
 Antimicrobial and Cytotoxic Activity from the Fungus Coniochaeta
 cephalothecoides Collected in Tibetan Plateau (Medog).
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11474
_journal_page_last               11486
_journal_paper_doi               10.1021/acs.joc.7b02010
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C24 H27 N O4, C H4 O'
_chemical_formula_sum            'C25 H31 N O5'
_chemical_formula_weight         425.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-01
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.23 svn.r3337 for OlexSys, GUI svn.r5217)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.3407(4)
_cell_length_b                   12.2598(4)
_cell_length_c                   25.8810(8)
_cell_measurement_reflns_used    5453
_cell_measurement_temperature    103.4
_cell_measurement_theta_max      70.8861
_cell_measurement_theta_min      3.0795
_cell_volume                     4550.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      103.4
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega   24.00   51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   77.0000  120.0000 27

  2 omega  -15.00   10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000  111.0000    0.0000 25

  3 omega  -29.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   77.0000  120.0000 29

  4 omega   35.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122 -112.0000 -133.0000 30

  5 omega  -32.00   53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -37.0000   60.0000 85

  6 omega   18.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000    0.0000 81

  7 omega   29.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122 -112.0000   40.0000 54

  8 omega   40.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 34

  9 omega   69.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 28

 10 omega  149.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -180.0000 25

 11 omega   42.00   82.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 40

 12 omega  129.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 49

 13 omega  148.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   33.0000  -73.0000 27

 14 omega   47.00   73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 26

 15 omega   76.00  134.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 58

 16 omega   40.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 17 omega   90.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   33.0000  -73.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0054110000
_diffrn_orient_matrix_UB_12      -0.0479880000
_diffrn_orient_matrix_UB_13      0.0548822000
_diffrn_orient_matrix_UB_21      0.1053644000
_diffrn_orient_matrix_UB_22      0.0243834000
_diffrn_orient_matrix_UB_23      0.0017015000
_diffrn_orient_matrix_UB_31      -0.0204263000
_diffrn_orient_matrix_UB_32      0.1134798000
_diffrn_orient_matrix_UB_33      0.0229035000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12859
_diffrn_reflns_theta_full        71.05
_diffrn_reflns_theta_max         71.05
_diffrn_reflns_theta_min         3.42
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+1.7556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                3847
_reflns_number_total             4339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02010_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4033021--4033022.cif.'
_cod_database_code               4033021
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H4(0.038) H3(0.031) H5(0.064) H1(0.02) H10(0.019) H11(0.018)
 H1A(0.018) H24(0.023) H16A(0.042) H16B(0.042) H16C(0.042) H23(0.024)
 H15A(0.025) H15B(0.025) H8(0.025) H7(0.023) H12A(0.022) H12B(0.022) H6(0.017)
 H17A(0.046) H17B(0.046) H17C(0.046) H20(0.029) H9(0.025) H18A(0.023)
 H18B(0.023) H13(0.025) H21(0.031) H25A(0.069) H25B(0.069) H25C(0.069)
 Fixed X: H4(-0.355) H3(0.0974) H5(-0.0519) H1(-0.0019) H10(0.2088)
 H11(0.1506) H1A(0.0561) H24(-0.1561) H16A(-0.0197) H16B(-0.0696) H16C(-0.1153)
 H23(-0.2568) H15A(0.2494) H15B(0.2023) H8(-0.0524) H7(-0.0373) H12A(0.2692)
 H12B(0.2839) H6(0.1183) H17A(0.4223) H17B(0.4571) H17C(0.3789) H20(-0.1819)
 H9(0.0773) H18A(-0.0865) H18B(-0.1068) H13(0.4015) H21(-0.2824) H25A(-0.1661)
 H25B(-0.1668) H25C(-0.0758)
 Fixed Y: H4(0.4211) H3(0.2408) H5(0.0807) H1(0.135) H10(0.6736) H11(0.4826)
 H1A(0.2945) H24(0.4985) H16A(0.4429) H16B(0.3887) H16C(0.4927) H23(0.5151)
 H15A(0.7445) H15B(0.6441) H8(0.6856) H7(0.5394) H12A(0.3955) H12B(0.4977)
 H6(0.5311) H17A(0.7189) H17B(0.5964) H17C(0.6478) H20(0.1706) H9(0.764)
 H18A(0.3902) H18B(0.2621) H13(0.4872) H21(0.1869) H25A(0.0986) H25B(0.1861)
 H25C(0.1719)
 Fixed Z: H4(0.3769) H3(0.3858) H5(0.3701) H1(0.2452) H10(0.3892) H11(0.4444)
 H1A(0.1932) H24(0.2509) H16A(0.4511) H16B(0.4021) H16C(0.4296) H23(0.3209)
 H15A(0.4692) H15B(0.4988) H8(0.4105) H7(0.3509) H12A(0.3996) H12B(0.3619)
 H6(0.3374) H17A(0.4911) H17B(0.5003) H17C(0.537) H20(0.2567) H9(0.4377)
 H18A(0.1834) H18B(0.1805) H13(0.4336) H21(0.3265) H25A(0.4498) H25B(0.4039)
 H25C(0.4391)
;