Clavipines A‒C, antiproliferative meroterpenoids with a fused azepine skeleton from the basidiomycete Clitocybe clavipes
Sun, Zhaocui; Zhu, Nailiang; Zhou, Man; Huo, Xiaowei; Wu, Haifeng; Tian, Yu; Yang, Junshan; Ma, Guoxu; Yang, Yan-Long; Xu, Xudong; Organic Chemistry Frontiers 6 (2019) 3759–; doi:10.1039/C9QO01005J

data_1555160
_publ_section_title
;
 Clavipines A--C, antiproliferative meroterpenoids with a fused azepine
 skeleton from the basidiomycete Clitocybe clavipes
;
_journal_issue                   22
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3759
_journal_paper_doi               10.1039/C9QO01005J
_journal_volume                  6
_journal_year                    2019
_chemical_compound_source        'Clitocybe Clavipes'
_chemical_formula_moiety         'C16 H14 O5'
_chemical_formula_sum            'C16 H14 O5'
_chemical_formula_weight         286.27
_chemical_name_common            'clavilactone A'
_chemical_properties_physical    Oxygen-sensitive
_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             2019-04-02
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2019-08-09 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5940(3)
_cell_length_b                   11.8962(8)
_cell_length_c                   13.1105(5)
_cell_measurement_reflns_used    2898
_cell_measurement_temperature    109.65(10)
_cell_measurement_theta_max      71.0300
_cell_measurement_theta_min      3.7630
_cell_volume                     1340.36(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      N~2~
_diffrn_ambient_temperature      109.65(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9733
_diffrn_measurement_details
;
  1 omega   21.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   56.0000   87.0000 82

  2 omega   40.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 51

  3 omega   62.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 29

  4 omega   54.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 43

  5 omega   58.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 32

  6 omega  111.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 63

  7 omega  107.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 48

  8 omega   61.00  147.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 86

  9 omega   38.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 49

 10 omega   34.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -150.0000 27

 11 omega    6.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000  -30.0000 68

 12 omega   83.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -178.0000    0.0000 25

 13 omega  -12.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -180.0000 67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1159411000
_diffrn_orient_matrix_UB_12      0.0272811000
_diffrn_orient_matrix_UB_13      0.0861128000
_diffrn_orient_matrix_UB_21      -0.0341695000
_diffrn_orient_matrix_UB_22      -0.1263447000
_diffrn_orient_matrix_UB_23      0.0131550000
_diffrn_orient_matrix_UB_31      0.1325148000
_diffrn_orient_matrix_UB_32      -0.0086327000
_diffrn_orient_matrix_UB_33      0.0788693000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4265
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.981
_diffrn_reflns_theta_min         5.020
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ??
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ????'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 1010 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.2780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.0991
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2491
_reflns_number_total             2530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo01005j2.cif
_cod_data_source_block           exp_5895
_cod_original_cell_volume        1340.37(12)
_cod_database_code               1555160
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.843
_shelx_estimated_absorpt_t_min   0.809
_shelx_res_checksum              36002
_shelx_shelxl_version_number     2014/7