Cantharimide and Its Derivatives from the Blister Beetle Mylabris phalerata Palla.
Zeng, Yao-Bo; Liu, Xiao-Ling; Zhang, Yi; Li, Chuang-Jun; Zhang, Dong-Ming; Peng, Yao-Zong; Zhou, Xing; Du, Hong-Fei; Tan, Chun-Bing; Zhang, Yu-Yu; Yang, Da-Jian; Journal of natural products 79 (2016) 2032–2038; doi:10.1021/acs.jnatprod.6b00332

data_1553296
_publ_section_title
;
 Cantharimide and Its Derivatives from the Blister Beetle Mylabris
 phalerata Palla.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2032
_journal_page_last               2038
_journal_paper_doi               10.1021/acs.jnatprod.6b00332
_journal_volume                  79
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H11 N O3'
_chemical_formula_sum            'C9 H11 N O3'
_chemical_formula_weight         181.19
_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             2016-04-07
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3760(5)
_cell_length_b                   11.9366(11)
_cell_length_c                   13.1122(13)
_cell_measurement_reflns_used    1699
_cell_measurement_temperature    104.3
_cell_measurement_theta_max      70.9423
_cell_measurement_theta_min      3.3678
_cell_volume                     841.43(14)
_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  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      104.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega  -67.00  -37.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -45.0000   90.0000 30

  2 omega   10.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -106.0000 -101.0000 48

  3 omega   57.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000   30.0000 39

  4 omega  -24.00   54.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  -30.0000 78

  5 omega   61.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  -60.0000 40

  6 omega   79.00  158.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 79

  7 omega   42.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 55

  8 omega   54.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 36

  9 omega  103.00  168.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 65

 10 omega  102.00  157.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 55

 11 omega   40.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 44

 12 omega  116.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 62
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.2032358000
_diffrn_orient_matrix_UB_12      0.0763688000
_diffrn_orient_matrix_UB_13      0.0449305000
_diffrn_orient_matrix_UB_21      -0.1011634000
_diffrn_orient_matrix_UB_22      -0.0990996000
_diffrn_orient_matrix_UB_23      0.0631078000
_diffrn_orient_matrix_UB_31      0.1747179000
_diffrn_orient_matrix_UB_32      0.0315039000
_diffrn_orient_matrix_UB_33      0.0884395000
_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     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2545
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.080
_diffrn_reflns_theta_min         5.010
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88544
_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_density_diffrn    1.430
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0673P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                1551
_reflns_number_total             1588
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            13.cif
_cod_data_source_block           exp_3938
_cod_database_code               1553296
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.840
_shelx_estimated_absorpt_t_min   0.806
_shelx_hkl_checksum              57676
_shelx_res_checksum              41317
_shelx_shelxl_version_number     2014/7