Dimericbiscognienyne A: A Meroterpenoid Dimer from Biscogniauxia sp. with New Skeleton and Its Activity.
Zhao, Huan; Chen, Guo-Dong; Zou, Jian; He, Rong-Rong; Qin, Sheng-Ying; Hu, Dan; Li, Guo-Qiang; Guo, Liang-Dong; Yao, Xin-Sheng; Gao, Hao; Organic letters  (2016) –; doi:10.1021/acs.orglett.6b03264

data_1544950
_publ_section_title
;
 Dimericbiscognienyne A: A Meroterpenoid Dimer from Biscogniauxia sp. with
 New Skeleton and Its Activity.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.6b03264
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C32 H40 O6), 2(H2 O)'
_chemical_formula_sum            'C64 H84 O14'
_chemical_formula_weight         1077.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.3962(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.2191(4)
_cell_length_b                   14.0289(2)
_cell_length_c                   18.0170(2)
_cell_measurement_reflns_used    22744
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      62.9010
_cell_measurement_theta_min      3.6700
_cell_volume                     5955.03(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000    0.0000 52

  2 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000 -180.0000 89

  3 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000  -30.0000 100

  4 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000  120.0000 100

  5 omega    8.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000  120.0000 98

  6 omega    8.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000 -120.0000 98

  7 omega    8.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000 -150.0000 98

  8 omega   35.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  178.0000   30.0000 74

  9 omega    8.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000  150.0000 98

 10 omega  -36.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -57.0000    0.0000 91

 11 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  120.0000 89

 12 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000 -150.0000 89

 13 omega   60.00  161.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -180.0000 101

 14 omega   60.00  161.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  150.0000 101

 15 omega   60.00  161.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  120.0000 101

 16 omega   69.00  159.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  150.0000 90

 17 omega   18.00   90.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -150.0000 72

 18 omega   17.00  144.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -15.0000 -156.0000 127

 19 omega   69.00  159.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -180.0000 90

 20 omega   69.00  159.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   60.0000 90

 21 omega   69.00  159.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   90.0000 90

 22 omega   69.00  159.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  120.0000 90

 23 omega   79.00  163.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000 -180.0000 84

 24 omega   18.00   90.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  150.0000 72

 25 omega   60.00  161.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   30.0000 101

 26 omega   18.00   69.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   90.0000 51

 27 omega   18.00   69.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   60.0000 51

 28 omega   19.00   77.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   90.0000 58

 29 omega   22.00  112.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000   60.0000 90

 30 omega   18.00   69.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -120.0000 51

 31 omega   67.00  162.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000 -150.0000 95

 32 omega   67.00  162.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  150.0000 95

 33 omega   30.00   56.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000    0.0000 26

 34 omega   77.00  119.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000    0.0000 42

 35 omega   60.00   86.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   60.0000 26

 36 omega  104.00  130.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000    0.0000 26

 37 omega   37.00   65.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -95.0000   90.0000 28

 38 omega   29.00   57.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   30.0000 28

 39 omega   69.00   98.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   90.0000 29

 40 omega  132.00  158.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 26

 41 omega   67.00  106.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   60.0000 39

 42 omega   60.00   86.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 26

 43 omega   69.00  154.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  120.0000 85

 44 omega   90.00  129.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000   46.7775 39

 45 omega   66.00  113.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000    0.0000 47

 46 omega  138.00  163.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000    0.0000 25

 47 omega   22.00   63.00   1.0000    2.5850
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000   46.7775 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0082627000
_diffrn_orient_matrix_UB_12      -0.0072162000
_diffrn_orient_matrix_UB_13      0.0872006000
_diffrn_orient_matrix_UB_21      0.0637030000
_diffrn_orient_matrix_UB_22      0.0216386000
_diffrn_orient_matrix_UB_23      0.0103413000
_diffrn_orient_matrix_UB_31      -0.0123035000
_diffrn_orient_matrix_UB_32      0.1074095000
_diffrn_orient_matrix_UB_33      0.0037354000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45934
_diffrn_reflns_theta_full        62.76
_diffrn_reflns_theta_max         62.76
_diffrn_reflns_theta_min         3.67
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             2320
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     720
_refine_ls_number_reflns         9082
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0789P)^2^+4.2855P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                8626
_reflns_number_total             9082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03264_si_002.cif
_cod_data_source_block           comp1
_cod_original_cell_volume        5955.00(14)
_cod_database_code               1544950
_reflns_odcompleteness_completeness 97.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_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, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1C) = Uanis(C16B)
3. Others
 Sof(C16B)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(H1CC)=FVAR(1)
4.a Riding coordinates:
 C1E(O8A,H8AA,H8AB), C1E(O7A,H7AA,H7AB)
4.b Ternary CH refined with riding coordinates:
 C7'(H7'), C7A'(H7A'), C4(H4B), C4'(H4'), C3'(H3'), C3(H3), C5A(H5A), C9(H9),
 C4A(H4AA), C1A'(H1A'), C3A(H3A), C3A'(H3A'), C1'(H1'), C4A'(H4A')
4.c Secondary CH2 refined with riding coordinates:
 C12(H12C,H12D), C10A(H10A,H10B), C12A(H12A,H12B), C10'(H10E,H10F), C10(H10C,
 H10D), C12'(H12E,H12F)
4.d Aromatic/amide H refined with riding coordinates:
 C8A'(H8A'), C13(H13), C5A'(H5A'), C5'(H5'), C13'(H13'), C8'(H8'), C13A(H13A),
 C19(H19)
4.e X=CH2 refined with riding coordinates:
 C15(H15D,H15E), C1D(H1DA,H1DB)
4.f Idealised Me refined as rotating group:
 C11A(H11A,H11B,H11C), C11'(H11D,H11E,H11F), C16'(H16G,H16H,H16I), C16(H16J,
 H16K,H16L), C15A(H15A,H15B,H15C), C15'(H15F,H15G,H15H), C16A(H16A,H16B,H16C),
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB,
 H1CC), C1E(H1EA,H1EB,H1EC), C16B(H16D,H16E,H16F)
4.g Idealised tetrahedral OH refined as rotating group:
 O2A(H2A), O4A(H4A), O6A(H6A), O2(H2), O4(H4), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'