Archromones A-F, unusual polycyclic dearomatic geranylquinol derivatives from the roots of <i>Arnebia euchroma</i>.
Yan, Hai-Wei; Zhang, Xu; Yang, Ya-Nan; Feng, Zi-Ming; Jiang, Jian-Shuang; Zhang, Pei-Cheng; Organic & biomolecular chemistry 18 (2020) 8424–8432; doi:10.1039/d0ob01934h

data_7157730
_publ_section_title
;
 Archromones A-F, unusual polycyclic dearomatic geranylquinol derivatives
 from the roots of <i>Arnebia euchroma</i>.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8424
_journal_page_last               8432
_journal_paper_doi               10.1039/d0ob01934h
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H18 O5, H2 O'
_chemical_formula_sum            'C16 H20 O6'
_chemical_formula_weight         308.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-12-09
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2020-07-12 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.346(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1628(6)
_cell_length_b                   13.0501(8)
_cell_length_c                   13.9274(10)
_cell_measurement_reflns_used    2479
_cell_measurement_temperature    111.95(10)
_cell_measurement_theta_max      70.9840
_cell_measurement_theta_min      5.5470
_cell_volume                     1443.55(18)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      111.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9719
_diffrn_measurement_details
;
  1 omega   26.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  -60.0000 80

  2 omega  131.00  172.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 41

  3 omega  140.00  172.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 32

  4 omega  151.00  176.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 25

  5 omega  131.00  175.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 44

  6 omega   93.00  118.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 25

  7 omega   92.00  117.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 25

  8 omega   94.00  122.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 28

  9 omega   93.00  150.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 57

 10 omega   94.00  119.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   30.0000 25

 11 omega   92.00  123.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 31

 12 omega   91.00  117.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 26

 13 omega   87.00  177.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 90

 14 omega   91.00  175.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 84

 15 omega   62.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  120.0000 28

 16 omega   13.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  120.0000 52

 17 omega   50.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 41

 18 omega   39.00  102.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 63

 19 omega   65.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 26

 20 omega   42.00   67.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 25

 21 omega   38.00   96.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 58

 22 omega    8.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000  -90.0000 31

 23 omega  -32.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000 -150.0000 82

 24 omega  -25.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919    0.0000 -120.0000 109

 25 omega   40.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 51

 26 omega   42.00  100.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 58

 27 omega   63.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000 -180.0000 32

 28 omega   59.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  -90.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1418716000
_diffrn_orient_matrix_UB_12      -0.0080371000
_diffrn_orient_matrix_UB_13      0.0943036000
_diffrn_orient_matrix_UB_21      -0.0839637000
_diffrn_orient_matrix_UB_22      -0.0964185000
_diffrn_orient_matrix_UB_23      0.0309898000
_diffrn_orient_matrix_UB_31      0.1022537000
_diffrn_orient_matrix_UB_32      -0.0679302000
_diffrn_orient_matrix_UB_33      -0.0553312000
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0420
_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       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4617
_diffrn_reflns_theta_full        71.17
_diffrn_reflns_theta_max         71.17
_diffrn_reflns_theta_min         6.52
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83677
_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    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.3276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                2644
_reflns_number_total             2729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob01934h2.cif
_cod_data_source_block           exp_6254
_cod_depositor_comments
'Adding full bibliography for 7157730--7157733.cif.'
_cod_original_cell_volume        1443.55(17)
_cod_database_code               7157730
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97