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_7228396
_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         'C18 H26 O5'
_chemical_formula_sum            'C18 H26 O5'
_chemical_formula_weight         322.39
_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             2016-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-02-24 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.846(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1708(4)
_cell_length_b                   18.5668(8)
_cell_length_c                   11.4565(6)
_cell_measurement_reflns_used    2470
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.0730
_cell_measurement_theta_min      3.8600
_cell_volume                     1725.62(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -47.00  -6.00   1.00    1.00    --  -70.50  30.00   0.00   41
  2  \w    -41.00   7.00   1.00    1.00    --  -24.71 -57.00  30.00   48
  3  \w    -17.00  14.00   1.00    1.00    --  -24.71 -77.00 -30.00   31
  4  \w    -70.00 -35.00   1.00    1.00    --  -70.50 -69.00  26.02   35
  5  \w    -58.00 -31.00   1.00    1.00    --  -70.50 -77.00  60.00   27
  6  \w    -57.00 -31.00   1.00    1.00    --  -70.50 -77.00 120.00   26
  7  \w    -64.00 -32.00   1.00    1.00    --  -70.50 -77.00  90.00   32
  8  \w    -99.00 -16.00   1.00    1.00    --  -24.71 -57.00 150.00   83
  9  \w     31.00  58.00   1.00    1.00    --   70.97  77.00  90.00   27
 10  \w     56.00 144.00   1.00    1.00    --   70.97  61.00 120.00   88
 11  \w    101.00 144.00   1.00    1.00    --   70.97 111.00  30.00   43
 12  \w    109.00 146.00   1.00    1.00    --   70.97 111.00 -60.00   37
 13  \w    101.00 130.00   1.00    1.00    --   70.97 111.00-120.00   29
 14  \w    116.00 177.00   1.00    1.00    --  117.22 104.00-120.00   61
 15  \w    107.00 159.00   1.00    1.00    --  117.22  77.00  30.00   52
 16  \w    129.00 169.00   1.00    1.00    --  117.22  63.00 150.00   40
 17  \w     96.00 127.00   1.00    1.00    --   70.97  77.00  60.00   31
 18  \w     85.00 178.00   1.00    1.00    --  117.22  63.00  60.00   93
 19  \w     84.00 111.00   1.00    1.00    --  117.22  63.00 150.00   27
 20  \w     78.00 173.00   1.00    1.00    --  117.22  77.00 120.00   95
 21  \w     84.00 110.00   1.00    1.00    --  117.22  63.00  90.00   26
 22  \w     78.00 176.00   1.00    1.00    --  117.22  77.00  90.00   98
 23  \w     84.00 110.00   1.00    1.00    --  117.22  63.00  30.00   26
 24  \w     77.00 160.00   1.00    1.00    --  117.22  77.00   0.00   83
 25  \w     77.00 104.00   1.00    1.00    --  117.22  77.00 105.44   27
 26  \w     78.00 105.00   1.00    1.00    --  117.22  77.00  60.00   27
 27  \w     78.00 105.00   1.00    1.00    --  117.22  77.00  30.00   27
 28  \w     74.00 101.00   1.00    1.00    --  117.22  38.00  90.00   27
 29  \w     73.00  99.00   1.00    1.00    --  117.22  38.00 120.00   26
 30  \w     73.00 100.00   1.00    1.00    --  117.22  38.00 150.00   27
 31  \w     71.00  98.00   1.00    1.00    --  117.22  38.00  60.00   27
 32  \w     48.00  75.00   1.00    1.00    --  117.22  25.00 120.00   27
 33  \w     32.00  59.00   1.00    1.00    --   70.97  77.00  30.00   27
 34  \w     33.00  60.00   1.00    1.00    --   70.97  77.00  60.00   27
 35  \w     42.00  90.00   1.00    1.00    --  117.22 -38.00   0.00   48
 36  \w     77.00 136.00   1.00    1.00    --  117.22 -63.00 -90.00   59
 37  \w     72.00 178.00   1.00    1.00    --  117.22  38.00-180.00  106
 38  \w     57.00 139.00   1.00    1.00    --   70.97 178.00-120.00   82
 39  \w     38.00  66.00   1.00    1.00    --  117.22 -38.00  30.00   28
 40  \w     78.00 105.00   1.00    1.00    --  117.22-104.00 120.00   27
 41  \w     47.00  94.00   1.00    1.00    --  117.22-104.00  90.00   47
 42  \w     38.00  63.00   1.00    1.00    --  117.22-104.00 120.00   25
 43  \w     28.00  96.00   1.00    1.00    --   70.97 -94.00-150.00   68
 44  \w     50.00 103.00   1.00    1.00    --  117.22 -50.00-180.00   53
 45  \w     10.00  57.00   1.00    1.00    --   24.71 -99.00-180.00   47
 46  \w    -97.00  -2.00   1.00    1.00    --  -24.71 -57.00-120.00   95
 47  \w   -111.00 -38.00   1.00    1.00    --  -24.71-178.00-120.00   73
 48  \w   -125.00 -31.00   1.00    1.00    --  -70.50 -76.00  19.74   94
 49  \w   -143.00 -80.00   1.00    1.00    --  -70.50 -77.00  60.00   63
 50  \w   -147.00 -67.00   1.00    1.00    --  -70.50 -77.00  90.00   80
 51  \w    -57.00 -32.00   1.00    1.00    --  -70.50 -74.00  96.68   25
 52  \w    109.00 135.00   1.00    1.00    --  115.97  37.00 102.29   26
 53  \w     76.00 102.00   1.00    1.00    --  115.97  77.00  60.00   26
 54  \w     76.00 102.00   1.00    1.00    --  115.97  77.00  90.00   26
 55  \w     76.00 102.00   1.00    1.00    --  115.97  77.00 120.00   26
 56  \w     76.00 102.00   1.00    1.00    --  115.97  77.00  30.00   26
 57  \w     69.00  95.00   1.00    1.00    --  115.97  37.00 102.29   26
 58  \w     67.00  93.00   1.00    1.00    --  115.97  35.00  49.74   26
 59  \w     83.00 109.00   1.00    1.00    --  115.97  63.00  60.00   26
 60  \w     83.00 109.00   1.00    1.00    --  115.97  63.00 150.00   26
 61  \w     76.00 102.00   1.00    1.00    --  115.97  77.00   0.00   26
 62  \w     77.00 103.00   1.00    1.00    --  115.97  45.00  36.09   26
 63  \w    -68.00  51.00   1.00    1.00    --  -27.96  77.00  30.00  119
 64  \w   -107.00  12.00   1.00    1.00    --  -27.96 -77.00 150.00  119
 65  \w   -102.00   5.00   1.00    1.00    --  -27.96 -57.00  90.00  107
 66  \w   -107.00  12.00   1.00    1.00    --  -27.96 -77.00-120.00  119
 67  \w   -102.00   5.00   1.00    1.00    --  -27.96 -57.00 -60.00  107
 68  \w    -50.00  51.00   1.00    1.00    --  -27.96  38.00-120.00  101
 69  \w    -50.00  51.00   1.00    1.00    --  -27.96  38.00  90.00  101
 70  \w   -132.00 -34.00   1.00    1.00    --  -70.50 178.00-120.00   98
 71  \w   -150.00 -31.00   1.00    1.00    --  -70.50 -77.00 -41.92  119
 72  \w    -48.00  10.00   1.00    1.00    --  -70.50  30.00-180.00   58
 73  \w   -132.00 -34.00   1.00    1.00    --  -70.50 178.00-180.00   98
 74  \w   -150.00 -31.00   1.00    1.00    --  -70.50 -77.00-168.21  119
 75  \w   -150.00 -31.00   1.00    1.00    --  -70.50 -77.00-120.00  119
 76  \w   -132.00 -81.00   1.00    1.00    --  -70.50 178.00  90.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0943907000
_diffrn_orient_matrix_UB_12      -0.0067342000
_diffrn_orient_matrix_UB_13      -0.1081182000
_diffrn_orient_matrix_UB_21      0.1545369000
_diffrn_orient_matrix_UB_22      -0.0250506000
_diffrn_orient_matrix_UB_23      0.0798830000
_diffrn_orient_matrix_UB_31      -0.0571197000
_diffrn_orient_matrix_UB_32      -0.0788461000
_diffrn_orient_matrix_UB_33      -0.0162198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17078
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.124
_diffrn_reflns_theta_min         3.886
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.731
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1180 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         6161
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0714
_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^)+(0.1007P)^2^+0.7003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.2210
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                3526
_reflns_number_total             6161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra04267a2.cif
_cod_data_source_block           z-c
_cod_original_cell_volume        1725.63(14)
_cod_database_code               7228396
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C20(H20), C21(H21),
 C22(H22), C25(H25), C26(H26), C27(H27), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C11(H11A,H11B), C24(H24A,H24B), C29(H29A,H29B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,
 H33B,H33C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.820