Echingridimer A, an Oxaspiro Dimeric Sesquiterpenoid with a 6/6/5/6/6 Fused Ring System from <i>Echinops grijsii</i> and Aphicidal Activity Evaluation.
Liu, Tingting; Wu, Haibo; Jiang, Hongyun; Zhang, Lan; Zhang, Yanning; Mao, Liangang; The Journal of organic chemistry 84 (2019) 10757–10763; doi:10.1021/acs.joc.9b01212

data_4033858
_publ_section_title
;
 Echingridimer A, an Oxaspiro Dimeric Sesquiterpenoid with a 6/6/5/6/6
 Fused Ring System from <i>Echinops grijsii</i> and Aphicidal Activity
 Evaluation.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10757
_journal_page_last               10763
_journal_paper_doi               10.1021/acs.joc.9b01212
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H42 O4, 0.5(C6 H14)'
_chemical_formula_sum            'C33 H49 O4'
_chemical_formula_weight         509.72
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-10-18
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                108.971(5)
_cell_angle_beta                 90.502(4)
_cell_angle_gamma                107.466(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0294(4)
_cell_length_b                   12.7216(6)
_cell_length_c                   16.3848(10)
_cell_measurement_reflns_used    4800
_cell_measurement_temperature    106.6
_cell_measurement_theta_max      71.5542
_cell_measurement_theta_min      3.8756
_cell_volume                     1499.25(15)
_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      106.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega   49.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036 -102.0000 -127.0000 26

  2 omega   86.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -110.0000  -37.0000 25

  3 omega   62.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000   94.0000 47

  4 omega    2.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036 -102.0000 -127.0000 27

  5 omega    5.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036 -102.0000   24.0000 64

  6 omega   51.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -102.0000   52.0000 47

  7 omega    8.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036 -102.0000 -155.0000 58

  8 omega   51.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -102.0000 -155.0000 60

  9 omega  -21.00   18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000 -120.0000 39

 10 omega  -68.00  -39.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000 -120.0000 29

 11 omega   45.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 86

 12 omega  -29.00    7.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -45.0000  -30.0000 36

 13 omega  -16.00   61.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -77.0000   90.0000 77

 14 omega  -77.00  -36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -45.0000  -30.0000 41

 15 omega  -33.00   54.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -37.0000 -120.0000 87

 16 omega   74.00  118.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 44

 17 omega   24.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   45.0000    0.0000 31

 18 omega  -25.00   13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   45.0000    0.0000 38

 19 omega   33.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   70.0000  -91.0000 47

 20 omega   34.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   71.0000  177.0000 53

 21 omega   90.00  123.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   74.0000    5.0000 33

 22 omega   31.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   74.0000    5.0000 54

 23 omega  127.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 47

 24 omega   26.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   76.0000   68.0000 34

 25 omega   81.00  124.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 43

 26 omega  130.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 46

 27 omega   81.00  110.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 29

 28 omega  147.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 29

 29 omega   27.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   75.0000 -150.0000 92

 30 omega   81.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 63

 31 omega   81.00  162.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 81

 32 omega   81.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 31

 33 omega  131.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 44

 34 omega   81.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 36

 35 omega   70.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   78.0000  -77.0000 48

 36 omega   81.00  132.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 51

 37 omega   25.00   51.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   78.0000  -77.0000 26

 38 omega   81.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 92

 39 omega   78.00  118.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   79.0000  145.0000 40

 40 omega   81.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 94

 41 omega   89.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   79.0000  -28.0000 26

 42 omega   81.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 91

 43 omega   24.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   79.0000  145.0000 51

 44 omega   24.00   50.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   79.0000  -28.0000 26

 45 omega   81.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 91

 46 omega   28.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   79.0000   90.0000 58

 47 omega   24.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000  121.0000 25

 48 omega   18.00   43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   82.0000    6.0000 25

 49 omega   17.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000  173.0000 25

 50 omega   17.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000 -138.0000 25

 51 omega   81.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 90

 52 omega    7.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   88.0000  -54.0000 25

 53 omega   11.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   88.0000 -146.0000 25

 54 omega  106.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 69

 55 omega   10.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000   50.0000 25

 56 omega  100.00  166.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 66

 57 omega   -7.00   18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0000  106.0000  117.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1561780000
_diffrn_orient_matrix_UB_12      -0.0331572000
_diffrn_orient_matrix_UB_13      -0.0422911000
_diffrn_orient_matrix_UB_21      -0.1231665000
_diffrn_orient_matrix_UB_22      -0.1252610000
_diffrn_orient_matrix_UB_23      -0.0493517000
_diffrn_orient_matrix_UB_31      -0.0382949000
_diffrn_orient_matrix_UB_32      0.0385326000
_diffrn_orient_matrix_UB_33      -0.0761594000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19415
_diffrn_reflns_point_group_measured_fraction_full 0.885
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.697
_diffrn_reflns_theta_min         3.879
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79594
_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_density_diffrn    1.129
_exptl_crystal_description       Block
_exptl_crystal_F_000             558
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2769 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.17(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     706
_refine_ls_number_reflns         10018
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.0298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1482
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.770
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                8158
_reflns_number_total             10018
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01212_si_002.cif
_cod_data_source_block           exp_5170
_cod_original_cell_volume        1499.24(15)
_cod_database_code               4033858
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.925
_shelx_hkl_checksum              48025
_shelx_res_checksum              52382
_shelx_shelxl_version_number     2014/7