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_1553295
_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 rmad
_chemical_formula_moiety         'C10 H13 N O4'
_chemical_formula_sum            'C10 H13 N O4'
_chemical_formula_weight         211.21
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.33508(19)
_cell_length_b                   7.7336(2)
_cell_length_c                   16.8499(4)
_cell_measurement_reflns_used    2260
_cell_measurement_temperature    100.3
_cell_measurement_theta_max      70.7011
_cell_measurement_theta_min      6.0279
_cell_volume                     955.84(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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega  -16.00   48.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -88.0000  172.0000 64

  2 omega   45.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122 -164.0000 -157.0000 26

  3 omega  -30.00   50.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122  -36.0000  174.0000 80

  4 omega   22.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122 -116.0000  101.0000 60

  5 omega   64.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.8122 -164.0000  -47.0000 46

  6 omega   40.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

  7 omega  100.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 30

  8 omega  107.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 69

  9 omega   68.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 67

 10 omega  139.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 26

 11 omega  108.00  166.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 58

 12 omega   86.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 92
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1185765000
_diffrn_orient_matrix_UB_12      0.0278490000
_diffrn_orient_matrix_UB_13      0.0745729000
_diffrn_orient_matrix_UB_21      0.1471999000
_diffrn_orient_matrix_UB_22      -0.0876221000
_diffrn_orient_matrix_UB_23      0.0512929000
_diffrn_orient_matrix_UB_31      0.0914710000
_diffrn_orient_matrix_UB_32      0.1764924000
_diffrn_orient_matrix_UB_33      0.0136690000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2999
_diffrn_reflns_theta_full        70.84
_diffrn_reflns_theta_max         70.84
_diffrn_reflns_theta_min         6.30
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80897
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       orthorhombic
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(19)
_refine_ls_extinction_coef       0.030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0572P)^2^+0.2208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                1780
_reflns_number_total             1790
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            14.cif
_cod_data_source_block           exp_2759
_cod_database_code               1553295
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C4(H4A,H4B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'