Highly oxygenated caryophyllene-type and drimane-type sesquiterpenes from Pestalotiopsis adusta, an endophytic fungus of Sinopodophyllum hexandrum
Xiao, Jian; Lin, Libin; Hu, Jiayao; Jiao, Furong; Duan, Dongzhu; Zhang, Qiang; Tang, Haoyu; Gao, Jinming; Wang, Le; Wang, Xiaoling; RSC Adv. 7 (2017) 29071–; doi:10.1039/C7RA04267A

data_7228395
_publ_section_title
;
 Highly oxygenated caryophyllene-type and drimane-type sesquiterpenes from
 Pestalotiopsis adusta, an endophytic fungus of Sinopodophyllum hexandrum
;
_journal_issue                   46
_journal_name_full               'RSC Adv.'
_journal_page_first              29071
_journal_paper_doi               10.1039/C7RA04267A
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H30 O6'
_chemical_formula_sum            'C19 H30 O6'
_chemical_formula_weight         354.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-02-24 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.986(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8418(13)
_cell_length_b                   18.700(4)
_cell_length_c                   8.9930(15)
_cell_measurement_reflns_used    730
_cell_measurement_temperature    296.71(10)
_cell_measurement_theta_max      21.3780
_cell_measurement_theta_min      3.9660
_cell_volume                     981.1(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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 (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.71(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   10.00   43.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479   77.0000   60.0000 22

  2 omega   25.00   88.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   77.0000   30.0000 42

  3 omega  -45.00   40.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000  -60.0000 57

  4 omega   34.00   76.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854 -178.0000  -90.0000 28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0462401000
_diffrn_orient_matrix_UB_12      -0.0160485000
_diffrn_orient_matrix_UB_13      0.0634457000
_diffrn_orient_matrix_UB_21      -0.1124972000
_diffrn_orient_matrix_UB_22      0.0073899000
_diffrn_orient_matrix_UB_23      -0.0299656000
_diffrn_orient_matrix_UB_31      -0.0025950000
_diffrn_orient_matrix_UB_32      -0.0335356000
_diffrn_orient_matrix_UB_33      -0.0363519000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.1057
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3915
_diffrn_reflns_point_group_measured_fraction_full 0.801
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.492
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3072
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0743
_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^)+(0.0781P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.2249
_reflns_Friedel_coverage         0.546
_reflns_Friedel_fraction_full    0.590
_reflns_Friedel_fraction_max     0.581
_reflns_number_gt                1736
_reflns_number_total             3072
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra04267a2.cif
_cod_data_source_block           6a16
_cod_original_cell_volume        981.1(4)
_cod_database_code               7228395
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C8(H8), C1(H1), C5(H5), C9(H9), C7(H7), C4(H4A), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C11(H11A,H11B)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C0AA(H0AA,H0AB,H0AC)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              30702
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-13
_olex2_submission_special_instructions 'No special instructions were received'