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_1555159
_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_formula_moiety         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_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'
_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
;
2019-06-11 deposited with the CCDC.	2019-10-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.776(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0737(5)
_cell_length_b                   6.13340(19)
_cell_length_c                   13.8766(6)
_cell_measurement_reflns_used    3624
_cell_measurement_temperature    109.2(5)
_cell_measurement_theta_max      71.0160
_cell_measurement_theta_min      4.5660
_cell_volume                     816.45(6)
_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      109.2(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9721
_diffrn_measurement_details
;
  1 omega   23.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000  -90.0000 70

  2 omega   78.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000 -180.0000 25

  3 omega   94.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 81

  4 omega  103.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 71

  5 omega   96.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  140.0000  -77.0000 29

  6 omega   73.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  -30.0000 26

  7 omega   26.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000 -180.0000 38

  8 omega   49.00   76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 27

  9 omega   52.00   78.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 26

 10 omega   47.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 41

 11 omega   42.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 46

 12 omega   63.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 42

 13 omega   78.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 37

 14 omega   47.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -129.0000   36.0000 46

 15 omega   47.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 41

 16 omega   59.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 49

 17 omega   47.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 44

 18 omega   88.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 89

 19 omega   68.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  150.0000 34

 20 omega   20.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000    0.0000 58

 21 omega   10.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  150.0000 37

 22 omega   45.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 72

 23 omega   45.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 46

 24 omega   48.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 61

 25 omega   40.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 26

 26 omega   10.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -180.0000 27

 27 omega  -27.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -180.0000 25

 28 omega  -32.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -120.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1131350000
_diffrn_orient_matrix_UB_12      -0.0727938000
_diffrn_orient_matrix_UB_13      -0.0970105000
_diffrn_orient_matrix_UB_21      0.0301305000
_diffrn_orient_matrix_UB_22      -0.2402079000
_diffrn_orient_matrix_UB_23      0.0315599000
_diffrn_orient_matrix_UB_31      -0.1098857000
_diffrn_orient_matrix_UB_32      0.0092073000
_diffrn_orient_matrix_UB_33      0.0565037000
_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  0.0231
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5154
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.147
_diffrn_reflns_theta_min         4.610
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92162
_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_density_diffrn    1.437
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(8)
_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     236
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0635P)^2^+0.1327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                3030
_reflns_number_total             3091
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo01005j2.cif
_cod_data_source_block           exp_5894
_cod_database_code               1555159
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.821
_shelx_res_checksum              9249
_shelx_shelxl_version_number     2014/7