4,5-seco-Probotryenols A–C, a new type of sesquiterpenoids from Stachybotrys bisbyi
Bao, Yan-Ru; Chen, Guo-Dong; Gao, Hao; He, Rong-Rong; Wu, Yue-Hua; Li, Xiao-Xia; Hu, Dan; Wang, Chuan-Xi; Liu, Xing-Zhong; Li, Yan; Yao, Xin-Sheng; RSC Adv. 5 (2015) 46252–; doi:10.1039/C5RA07122D

data_7220550
_publ_section_title
;
 4,5-seco-Probotryenols A--C, a new type of sesquiterpenoids from
 Stachybotrys bisbyi
;
_journal_issue                   57
_journal_name_full               'RSC Adv.'
_journal_page_first              46252
_journal_paper_doi               10.1039/C5RA07122D
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H22 O2'
_chemical_formula_sum            'C15 H22 O2'
_chemical_formula_weight         234.33
_chemical_name_common            dehydrobotrydienol
_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             2015-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-04-18 deposited with the CCDC.
2015-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8587(3)
_cell_length_b                   10.9481(4)
_cell_length_c                   13.7817(5)
_cell_measurement_reflns_used    4035
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      62.6810
_cell_measurement_theta_min      3.2270
_cell_volume                     1336.63(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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_temperature      173.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000   30.0000 52

  2 omega    8.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000 -180.0000 98

  3 omega    8.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   38.0000  -90.0000 98

  4 omega   18.00   69.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -150.0000 51

  5 omega   61.00  163.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000   60.0000 102

  6 omega   19.00   77.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -180.0000 58

  7 omega   19.00   77.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000    0.0000 58

  8 omega   19.00   83.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   30.0000 64

  9 omega   18.00   90.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  -30.0000 72

 10 omega   19.00   83.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -180.0000 64

 11 omega   18.00   90.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -120.0000 72

 12 omega   19.00   77.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -90.0000 58

 13 omega   19.00   83.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  150.0000 64

 14 omega   18.00   90.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  150.0000 72

 15 omega   19.00   83.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000    0.0000 64

 16 omega   18.00   69.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000  -60.0000 51

 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    0.0000 89

 19 omega  -36.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184  -57.0000 -150.0000 91

 20 omega   69.00  159.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -30.0000 90

 21 omega   37.00  164.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000 -150.0000 127

 22 omega   60.00  123.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000   90.0000 63

 23 omega   61.00  163.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  -60.0000 102

 24 omega  137.00  162.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  -90.0000 25

 25 omega   86.00  112.00   1.0000    1.6650
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000  -90.0000 26

 26 omega -110.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.3684  178.0000 -120.0000 57

 27 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   57.0000  -60.0000 89

 28 omega    3.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   77.0000 -180.0000 101

 29 omega    3.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.3684   77.0000   60.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0715824000
_diffrn_orient_matrix_UB_12      -0.1218380000
_diffrn_orient_matrix_UB_13      0.0316859000
_diffrn_orient_matrix_UB_21      -0.1556357000
_diffrn_orient_matrix_UB_22      -0.0623860000
_diffrn_orient_matrix_UB_23      -0.0062314000
_diffrn_orient_matrix_UB_31      0.0300829000
_diffrn_orient_matrix_UB_32      -0.0327122000
_diffrn_orient_matrix_UB_33      -0.1069838000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12262
_diffrn_reflns_theta_full        62.86
_diffrn_reflns_theta_max         62.86
_diffrn_reflns_theta_min         5.16
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55772
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0730
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1022P)^2^+1.5243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1899
_refine_ls_wR_factor_ref         0.2014
_reflns_number_gt                1869
_reflns_number_total             2141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra07122d2.cif
_cod_data_source_block           dehydrobotrydienol
_cod_database_code               7220550
_reflns_odcompleteness_completeness 97.47
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'