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_1544951
_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 unk
_chemical_formula_moiety         'C16 H22 O3'
_chemical_formula_sum            'C16 H22 O3'
_chemical_formula_weight         262.34
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_symmetry_space_group_name_Hall  'P 31'
_symmetry_space_group_name_H-M   'P 31'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   14.6149(3)
_cell_length_b                   14.6149(3)
_cell_length_c                   6.24615(13)
_cell_measurement_reflns_used    6116
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      62.9610
_cell_measurement_theta_min      3.4520
_cell_volume                     1155.41(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -101.00  -67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000   30.0000 34

  2 omega  -93.00  -59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000  -90.0000 34

  3 omega -105.00  -59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000 -180.0000 46

  4 omega   14.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000   90.0000 38

  5 omega   34.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   19.0000 -150.0000 72

  6 omega  -10.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   19.0000 -150.0000 34

  7 omega  -68.00  -39.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000   90.0000 29

  8 omega   19.00   57.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -90.0000 38

  9 omega   25.00   56.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000  -30.0000 31

 10 omega   93.00  119.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  120.0000 26

 11 omega   61.00   87.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000  -30.0000 26

 12 omega   98.00  158.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  120.0000 60

 13 omega   23.00   86.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -60.0000 63

 14 omega   72.00   99.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   90.0000 27

 15 omega   76.00  108.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -150.0000 32

 16 omega   62.00  140.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 78

 17 omega   21.00   68.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000    0.0000 47

 18 omega   30.00   57.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -30.0000 27

 19 omega   19.00   83.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -90.0000 64

 20 omega  120.00  145.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -150.0000 25

 21 omega   22.00   78.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -121.0000  125.0000 56

 22 omega   86.00  157.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000   90.0000 71

 23 omega  104.00  129.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   90.0000 25

 24 omega   32.00   57.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  120.0000 25

 25 omega   61.00  114.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   60.0000 53

 26 omega   78.00  103.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -180.0000 25

 27 omega   60.00   85.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 25

 28 omega   69.00   94.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  120.0000 25

 29 omega  -71.00   13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.3684   91.0000   96.0000 84

 30 omega    3.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   77.0000  120.0000 101

 31 omega    9.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   43.0000  -17.0000 96

 32 omega    3.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   77.0000    0.0000 101

 33 omega    3.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   77.0000 -150.0000 101

 34 omega  -39.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684  -37.0000 -180.0000 98

 35 omega   67.00  162.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  -60.0000 95

 36 omega   19.00   93.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -91.0000  -16.0000 74

 37 omega   60.00  161.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -30.0000 101

 38 omega   60.00  161.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  150.0000 101

 39 omega   69.00  159.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -120.0000 90

 40 omega   19.00   83.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  150.0000 64

 41 omega   69.00  159.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000    0.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1178622000
_diffrn_orient_matrix_UB_12      -0.0326853000
_diffrn_orient_matrix_UB_13      -0.0069460000
_diffrn_orient_matrix_UB_21      0.0273063000
_diffrn_orient_matrix_UB_22      0.0995085000
_diffrn_orient_matrix_UB_23      -0.1319665000
_diffrn_orient_matrix_UB_31      -0.0134475000
_diffrn_orient_matrix_UB_32      -0.0620189000
_diffrn_orient_matrix_UB_33      -0.2081420000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            12639
_diffrn_reflns_theta_full        62.92
_diffrn_reflns_theta_max         62.92
_diffrn_reflns_theta_min         3.49
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.131
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             426
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       0.0068(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2487
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0516
_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^)+(0.1074P)^2^+0.0641P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                2467
_reflns_number_total             2487
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03264_si_003.cif
_cod_data_source_block           comp2
_cod_database_code               1544951
_chemical_oxdiff_formula         CHNO
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.683(2) 0.317(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C4(H4), C1(H1A)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1"(H1"A,H1"B)
3.c Aromatic/amide H refined with riding coordinates:
 C2"(H2"), C5(H5)
3.d Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2), O3(H3)
3.e X=CH2 refined with riding coordinates:
 C5'(H5'A,H5'B)
3.f Idealised Me refined as rotating group:
 C4"(H4"A,H4"B,H4"C), C5"(H5"A,H5"B,H5"C), C4'(H4'A,H4'B,H4'C)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'