Lecanicillones A–C, Three Dimeric Isomers of Spiciferone A with Cyclobutane Ring from an Entomopathogenic Fungus Lecanicillium sp. PR-M-3
Wang, Zai-ying; Sang, Xia-Nan; Sun, Ke; Huang, Sheng-dong; Chen, Sheng-shuang; Xue, Chunmei; Ban, Lanfeng; Li, Zhanlin; Hua, Huiming; Pei, Yuehu; Bai, Jiao; RSC Adv.  (2016) –; doi:10.1039/C6RA11422A

data_7226353
_publ_section_title
;
 Lecanicillones A--C, Three Dimeric Isomers of Spiciferone A with
 Cyclobutane Ring from an Entomopathogenic Fungus Lecanicillium sp. PR-M-3
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA11422A
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_compound_source        ' Lecanicillium sp. '
_chemical_formula_moiety         'C28 H32 O6'
_chemical_formula_sum            'C28 H32 O6'
_chemical_formula_weight         464.54
_chemical_name_systematic        'Lecanicillone A'
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-30
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_audit_update_record
;
2016-07-16 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.4452(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.0422(2)
_cell_length_b                   6.75793(12)
_cell_length_c                   15.1547(3)
_cell_measurement_reflns_used    5301
_cell_measurement_temperature    99.5
_cell_measurement_theta_max      70.8269
_cell_measurement_theta_min      2.9957
_cell_volume                     1199.49(4)
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.5
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega   -2.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000  -77.0000    0.0000 25

  2 omega  -20.00    5.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   45.0000 -180.0000 25

  3 omega  -55.00  -24.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000  -77.0000    0.0000 31

  4 omega  -31.00   52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -37.0000 -180.0000 83

  5 omega   10.00   46.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -46.0000  100.0000 36

  6 omega  -32.00   -6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -46.0000  100.0000 26

  7 omega  -25.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -37.0000  -30.0000 80

  8 omega   58.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000 -150.0000 34

  9 omega   19.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000    0.0000 87

 10 omega   21.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000  -90.0000 84

 11 omega   19.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000 -120.0000 26

 12 omega   33.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122   37.0000 -180.0000 51

 13 omega  130.00  164.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 34

 14 omega   81.00  107.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 26

 15 omega   71.00  178.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 107

 16 omega  107.00  134.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 27

 17 omega   93.00  120.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  120.0000 27

 18 omega   71.00   96.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 25

 19 omega   41.00   75.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 34

 20 omega   83.00  159.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 76

 21 omega  142.00  172.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 30

 22 omega   72.00   97.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -150.0000 25

 23 omega   81.00  107.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 24 omega  114.00  168.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 54

 25 omega  122.00  173.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 51

 26 omega  108.00  142.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 34

 27 omega   81.00  107.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 28 omega   77.00  103.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 26

 29 omega   42.00   86.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 44

 30 omega   96.00  123.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 27

 31 omega   82.00  107.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 25

 32 omega  131.00  174.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 43

 33 omega   94.00  120.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  150.0000 26

 34 omega   81.00  107.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

 35 omega  102.00  169.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 67

 36 omega   55.00   91.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 36
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0840733000
_diffrn_orient_matrix_UB_12      0.1304347000
_diffrn_orient_matrix_UB_13      0.0367381000
_diffrn_orient_matrix_UB_21      -0.0854518000
_diffrn_orient_matrix_UB_22      -0.0098524000
_diffrn_orient_matrix_UB_23      -0.0929817000
_diffrn_orient_matrix_UB_31      -0.0541612000
_diffrn_orient_matrix_UB_32      -0.1867101000
_diffrn_orient_matrix_UB_33      0.0304986000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8390
_diffrn_reflns_theta_full        70.96
_diffrn_reflns_theta_max         70.96
_diffrn_reflns_theta_min         3.00
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90151
_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_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4358
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0548P)^2^+0.2427P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                4269
_reflns_number_total             4358
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra11422a2.cif
_cod_data_source_block           exp_2571
_cod_database_code               7226353
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97