Bioactive Sesquiterpenes from the Edible Mushroom Flammulina velutipes and Their Biosynthetic Pathway Confirmed by Genome Analysis and Chemical Evidence.
Tao, Qiaoqiao; Ma, Ke; Yang, Yanlong; Wang, Kai; Chen, Baosong; Huang, Ying; Han, Junjie; Bao, Li; Liu, Xiao-Bin; Yang, Zhuliang; Yin, Wen-Bing; Liu, Hongwei; The Journal of organic chemistry 81 (2016) 9867–9877; doi:10.1021/acs.joc.6b01971

data_4037318
_publ_section_title
;
 Bioactive Sesquiterpenes from the Edible Mushroom Flammulina velutipes
 and Their Biosynthetic Pathway Confirmed by Genome Analysis and Chemical
 Evidence.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9867
_journal_page_last               9877
_journal_paper_doi               10.1021/acs.joc.6b01971
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C15 H24 O4'
_chemical_formula_sum            'C15 H24 O4'
_chemical_formula_weight         268.34
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-03-10
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0162(4)
_cell_length_b                   9.8847(6)
_cell_length_c                   20.6163(13)
_cell_measurement_reflns_used    2644
_cell_measurement_temperature    108.0
_cell_measurement_theta_max      70.5894
_cell_measurement_theta_min      4.2854
_cell_volume                     1429.80(15)
_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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      108.0
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega  -97.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000  150.0000 132

  2 omega  -36.00   27.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   45.0000    0.0000 63

  3 omega   19.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.1253  -98.0000   30.0000 25

  4 omega   40.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

  5 omega   40.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 56

  6 omega   40.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 83

  7 omega   55.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 26

  8 omega   46.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 45

  9 omega  106.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 42

 10 omega   47.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 34

 11 omega   91.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 84
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1938488000
_diffrn_orient_matrix_UB_12      0.0146581000
_diffrn_orient_matrix_UB_13      -0.0345110000
_diffrn_orient_matrix_UB_21      0.0513292000
_diffrn_orient_matrix_UB_22      -0.1463201000
_diffrn_orient_matrix_UB_23      0.0189899000
_diffrn_orient_matrix_UB_31      -0.0892123000
_diffrn_orient_matrix_UB_32      -0.0519392000
_diffrn_orient_matrix_UB_33      -0.0634919000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4452
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.725
_diffrn_reflns_theta_min         4.289
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97363
_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    1.247
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.380
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 1014 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.1020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1045
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                2587
_reflns_number_total             2684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01971_si_002.cif
_cod_data_source_block           exp_3889
_cod_database_code               4037318
_shelx_estimated_absorpt_t_max   0.771
_shelx_estimated_absorpt_t_min   0.771
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_res_checksum              86265
_shelx_hkl_checksum              96590
_shelx_shelxl_version_number     2014/7