Euphorikanin A, a Diterpenoid Lactone with a Fused 5/6/7/3 Ring System from Euphorbia kansui.
Fei, Dong-Qing; Dong, Le-Le; Qi, Feng-Ming; Fan, Gai-Xia; Li, Hui-Hong; Li, Zheng-Yu; Zhang, Zhan-Xin; Organic letters 18 (2016) 2844–2847; doi:10.1021/acs.orglett.6b01093

data_1543365
_publ_section_title
;
 Euphorikanin A, a Diterpenoid Lactone with a Fused 5/6/7/3 Ring System
 from Euphorbia kansui.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2844
_journal_page_last               2847
_journal_paper_doi               10.1021/acs.orglett.6b01093
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration none
_chemical_formula_moiety         'C20 H26 O3'
_chemical_formula_sum            'C20 H26 O3'
_chemical_formula_weight         314.41
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.66247(9)
_cell_length_b                   16.2362(2)
_cell_length_c                   16.4824(3)
_cell_measurement_reflns_used    5062
_cell_measurement_temperature    293.7(3)
_cell_measurement_theta_max      70.7730
_cell_measurement_theta_min      5.3760
_cell_volume                     1782.95(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.7(3)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega  -82.00  -57.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  120.0000 25

  2 omega  -78.00  -37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 41

  3 omega  -65.00  -24.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000 -120.0000 41

  4 omega   -1.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000  -60.0000 26

  5 omega   44.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000   90.0000 71

  6 omega  -10.00   26.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   19.0000  120.0000 36

  7 omega   30.00  121.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   19.0000  120.0000 91

  8 omega   51.00   96.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -180.0000 45

  9 omega   43.00  100.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -120.0000 57

 10 omega  139.00  165.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -90.0000 26

 11 omega  107.00  163.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000    0.0000 56

 12 omega  112.00  138.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -90.0000 26

 13 omega   53.00   84.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   90.0000 31

 14 omega   53.00   96.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -60.0000 43

 15 omega   40.00   79.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   30.0000 39

 16 omega  -25.00   71.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   54.0000   49.0000 96

 17 omega -114.00  -18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -54.0000  -94.0000 96

 18 omega   24.00  128.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   75.0000  166.6641 104

 19 omega  -17.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -38.0000   30.0000 104

 20 omega  -15.00   80.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -90.0000 95

 21 omega   68.00  175.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000 -150.0000 107
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1397772000
_diffrn_orient_matrix_UB_12      -0.0740954000
_diffrn_orient_matrix_UB_13      0.0146491000
_diffrn_orient_matrix_UB_21      0.0592918000
_diffrn_orient_matrix_UB_22      -0.0358011000
_diffrn_orient_matrix_UB_23      -0.0831571000
_diffrn_orient_matrix_UB_31      0.1743691000
_diffrn_orient_matrix_UB_32      -0.0472515000
_diffrn_orient_matrix_UB_33      0.0400809000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8123
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         70.659
_diffrn_reflns_theta_min         3.821
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1076 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.12(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0770P)^2^+0.1196P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1163
_reflns_Friedel_coverage         0.603
_reflns_Friedel_fraction_full    0.851
_reflns_Friedel_fraction_max     0.820
_reflns_number_gt                2979
_reflns_number_total             3140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01093_si_002.cif
_cod_data_source_block           feidq_dll30
_cod_depositor_comments          'Adding full bibliography for 1543365.cif.'
_cod_original_cell_volume        1782.96(4)
_cod_database_code               1543365
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.89
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C12(H12)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              64412
_shelx_hkl_checksum              93511
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'