Xylariterpenoids A–D, four new sesquiterpenoids from the Xylariaceae fungus
Wu, Zu-Yan; Wu, Yang; Chen, Guo-Dong; Hu, Dan; Li, Xiao-Xia; Sun, Xiang; Guo, Liang-Dong; Li, Yan; Yao, Xin-Sheng; Gao, Hao; RSC Adv.  (2014) –; doi:10.1039/C4RA10365C

data_7218531
_publ_section_title
;
 Xylariterpenoids A--D, four new sesquiterpenoids from the Xylariaceae
 fungus
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA10365C
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C15 H24 O2'
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         236.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-06
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5259(3)
_cell_length_b                   13.1402(5)
_cell_length_c                   15.6863(7)
_cell_measurement_reflns_used    3277
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      62.4690
_cell_measurement_theta_min      4.3850
_cell_volume                     1345.13(10)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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  -43.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  -77.0000 -150.0000 37

  2 omega   13.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000  150.0000 79

  3 omega   15.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000   30.0000 85

  4 omega   22.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -180.0000 27

  5 omega   24.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -120.0000 29

  6 omega   36.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000 -180.0000 91

  7 omega   44.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -90.0000  129.6318 73

  8 omega   48.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   30.0000 31

  9 omega  111.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000   90.0000 48

 10 omega   21.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000   30.0000 59

 11 omega   31.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -91.0000   41.3662 34

 12 omega   80.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -91.0000   41.3662 26

 13 omega   70.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -150.0000 35

 14 omega   69.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -60.0000 69

 15 omega   18.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -60.0000 25

 16 omega   95.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000    0.0000 26

 17 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000   90.0000 52

 18 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  -60.0000 89

 19 omega  -39.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -38.0000  -30.0000 98

 20 omega   60.00  161.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 101

 21 omega   67.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000 -180.0000 95

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

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

 24 omega   19.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -90.0000 64

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

 26 omega   69.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   60.0000 78

 27 omega   67.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000   30.0000 95
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0325550000
_diffrn_orient_matrix_UB_12      -0.0264739000
_diffrn_orient_matrix_UB_13      0.0947050000
_diffrn_orient_matrix_UB_21      0.0035569000
_diffrn_orient_matrix_UB_22      -0.1141223000
_diffrn_orient_matrix_UB_23      -0.0222685000
_diffrn_orient_matrix_UB_31      0.2338770000
_diffrn_orient_matrix_UB_32      -0.0019389000
_diffrn_orient_matrix_UB_33      0.0135982000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10952
_diffrn_reflns_theta_full        62.93
_diffrn_reflns_theta_max         62.93
_diffrn_reflns_theta_min         4.39
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93252
_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            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0454P)^2^+0.0727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                1950
_reflns_number_total             2157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra10365c2.cif
_cod_data_source_block           chenguodong_63-19-7-3w2f-1-2
_cod_original_cell_volume        1345.12(10)
_cod_database_code               7218531
_chemical_oxdiff_formula         CHON
_reflns_odcompleteness_completeness 97.59
_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
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B), C15(H15A,H15B), C1(H1A,H1B), C5(H5A,H5B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'