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_1544949
_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         'C12 H12 O4, 0.25(H2 O)'
_chemical_formula_sum            'C12 H12.5 O4.25'
_chemical_formula_weight         224.72
_chemical_name_systematic
;
 ? 
;
_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                 107.661(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.8700(6)
_cell_length_b                   6.66620(10)
_cell_length_c                   13.8578(3)
_cell_measurement_reflns_used    8612
_cell_measurement_temperature    173.0(3)
_cell_measurement_theta_max      62.8500
_cell_measurement_theta_min      3.7290
_cell_volume                     2189.18(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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      173.0(3)
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -97.00  -58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  178.0000  -60.0000 39

  2 omega -101.00  -66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000   60.0000 35

  3 omega   15.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000 -120.0000 85

  4 omega  -36.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -57.0000  -30.0000 90

  5 omega  -29.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -38.0000   90.0000 47

  6 omega   31.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  120.0000 69

  7 omega   70.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  -90.0000 26

  8 omega   49.00   83.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   90.0000 34

  9 omega   19.00   73.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  120.0000 54

 10 omega   19.00   76.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -90.0000 57

 11 omega  106.00  158.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  150.0000 52

 12 omega   38.00   86.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000    0.0000 48

 13 omega   19.00   90.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000   90.0000 71

 14 omega   93.00  155.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -30.0000 62

 15 omega   20.00   68.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -150.0000 48

 16 omega   83.00  152.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -180.0000 69

 17 omega   22.00   69.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   30.0000 47

 18 omega   98.00  126.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -88.0000  110.1800 28

 19 omega   33.00   85.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000    0.0000  -30.0000 52

 20 omega   98.00  162.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000    0.0000  -30.0000 64

 21 omega   59.00   94.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000 -120.0000 35

 22 omega   69.00   95.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  150.0000 26

 23 omega   61.00  133.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  120.0000 72

 24 omega   41.00   67.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -88.0000  110.1800 26

 25 omega   31.00   66.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000  -30.0000 35

 26 omega  139.00  164.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000    0.0000 25

 27 omega   52.00   85.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -180.0000 33

 28 omega   24.00   79.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000   60.0000 55

 29 omega   73.00   98.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 25

 30 omega   70.00   96.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   60.0000 26

 31 omega   41.00   93.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000 -180.0000 52

 32 omega   78.00  156.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -90.0000 78

 33 omega -110.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  178.0000   90.0000 57

 34 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000 -180.0000 52

 35 omega   32.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184 -178.0000    0.0000 78

 36 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000   30.0000 89

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

 38 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  -30.0000 89

 39 omega -134.00  -34.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000 -180.0000 100

 40 omega -134.00  -35.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -75.0000  -96.5659 99

 41 omega -134.00  -34.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -77.0000  120.0000 100

 42 omega -134.00  -33.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -64.0000  -78.0000   18.5747 101

 43 omega   67.00  162.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   30.0000 95

 44 omega   60.00  161.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -120.0000 101

 45 omega   18.00   90.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000   30.0000 72

 46 omega   60.00  161.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -60.0000 101

 47 omega   60.00  161.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -180.0000 101

 48 omega   69.00  159.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   90.0000 90

 49 omega   19.00   83.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -60.0000 64

 50 omega   19.00   83.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -120.0000 64

 51 omega   19.00   83.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  150.0000 64

 52 omega   60.00  161.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -30.0000 101

 53 omega   60.00  111.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   30.0000 51

 54 omega   60.00  161.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -150.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0433102000
_diffrn_orient_matrix_UB_12      -0.0665504000
_diffrn_orient_matrix_UB_13      -0.0490164000
_diffrn_orient_matrix_UB_21      -0.0933371000
_diffrn_orient_matrix_UB_22      0.0822577000
_diffrn_orient_matrix_UB_23      -0.0427200000
_diffrn_orient_matrix_UB_31      0.0514096000
_diffrn_orient_matrix_UB_32      0.2054289000
_diffrn_orient_matrix_UB_33      0.0012157000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17988
_diffrn_reflns_theta_full        62.79
_diffrn_reflns_theta_max         62.79
_diffrn_reflns_theta_min         3.35
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             948
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0588P)^2^+0.3683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                3338
_reflns_number_total             3462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03264_si_004.cif
_cod_data_source_block           comp5
_cod_depositor_comments
;

2019-08-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         449.44
_cod_original_formula_moiety         '2(C12 H12 O4), 0.5(H2 O)'
_cod_original_formula_units_Z            4
_cod_original_formula_sum        'C24 H25 O8.50'
_cod_database_code               1544949
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 91.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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. Others
 Fixed Sof: H5AA(0.5) H5AB(0.5)
3.a Free rotating group:
 O5A(H5AA,H5AB)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C11A(H11C,H11D)
3.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C5A(H5A), C3(H3), C5(H5), C3A(H3AA), C9A(H9A), C8(H8), C2(H2),
 C8A(H8A), C9(H9)
3.d Tetrahedral OH refined with riding coordinates:
 O3A(H3A), O1(H1)
3.e Idealised Me refined as rotating group:
 C12A(H12D,H12E,H12F), C12(H12A,H12B,H12C)
3.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O4A(H4A)
;
_olex2_submission_special_instructions 'No special instructions were received'