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_7157733
_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 O3'
_chemical_formula_sum            'C16 H18 O3'
_chemical_formula_weight         258.30
_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     dual
_audit_creation_date             2019-10-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-12 deposited with the CCDC.	2020-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.16170(10)
_cell_length_b                   9.7401(2)
_cell_length_c                   18.6984(3)
_cell_measurement_reflns_used    10120
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      74.7620
_cell_measurement_theta_min      4.7460
_cell_volume                     1304.32(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -121.00 -38.00   0.50    0.05    --  -47.70 -36.00-166.00  166
  2  \w   -128.00 -89.00   0.50    0.07    -- -101.00 -86.00  23.00   78
  3  \w   -173.00-141.00   0.50    0.07    -- -101.00 -86.00  23.00   64
  4  \w     31.00  88.00   0.50    0.07    --  103.25-144.00 -32.00  114
  5  \w   -119.00 -93.00   0.50    0.05    --  -47.70-125.00 -30.00   52
  6  \w   -111.00 -85.00   0.50    0.05    --  -47.70-125.00  90.00   52
  7  \w     25.00  91.00   0.50    0.05    --   47.70-125.00-120.00  132
  8  \w    -73.00 -36.00   0.50    0.07    -- -101.00 125.00 150.00   74
  9  \w   -110.00 -77.00   0.50    0.07    -- -101.00 125.00 150.00   66
 10  \w   -104.00 -79.00   0.50    0.07    -- -101.00  30.00-180.00   50
 11  \w   -120.00 -35.00   0.50    0.07    -- -101.00  77.00  30.00  170
 12  \w    -72.00 -29.00   0.50    0.07    -- -101.00  30.00-180.00   86
 13  \w   -169.00 -91.00   0.50    0.07    -- -101.00-125.00  90.00  156
 14  \w     49.00 103.00   0.50    0.07    --  103.25-126.00 136.00  108
 15  \w    100.00 125.00   0.50    0.07    --  103.25-144.00 -32.00   50
 16  \w   -103.00 -76.00   0.50    0.05    --  -47.70-125.00  60.00   54
 17  \w     34.00  60.00   0.50    0.07    --  103.25-125.00  30.00   52
 18  \w    -71.00 -46.00   0.50    0.07    -- -101.00  36.00 -10.00   50
 19  \w    107.00 132.00   0.50    0.07    --  103.25  86.00 141.00   50
 20  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 -30.00  188
 21  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00  60.00  188
 22  \w   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00 120.00  172
 23  \w    -24.00  74.00   0.50    0.05    --   47.70 -86.00  23.00  196
 24  \w   -174.00-123.00   0.50    0.07    -- -101.00 -30.00 120.00  102
 25  \w     90.00 178.00   0.50    0.07    --  103.25  15.00-120.00  176
 26  \w      1.00  26.00   0.50    0.05    --   47.70 -86.00  23.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0257726000
_diffrn_orient_matrix_UB_12      0.0018801000
_diffrn_orient_matrix_UB_13      0.0818066000
_diffrn_orient_matrix_UB_21      -0.1900882000
_diffrn_orient_matrix_UB_22      -0.0723810000
_diffrn_orient_matrix_UB_23      -0.0083117000
_diffrn_orient_matrix_UB_31      0.0973579000
_diffrn_orient_matrix_UB_32      -0.1405845000
_diffrn_orient_matrix_UB_33      0.0053884000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12549
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.233
_diffrn_reflns_theta_min         4.730
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0453P)^2^+0.3062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                2473
_reflns_number_total             2589
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01934h2.cif
_cod_data_source_block           yhw_43a
_cod_depositor_comments
'Adding full bibliography for 7157730--7157733.cif.'
_cod_database_code               7157733
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.840
_diffrn_oxdiff_digest_frames
;
01d99e55b864864eb2f949961240742c540269626e3
;
_diffrn_oxdiff_digest_hkl
;
01062fb321597750d869354b3f545fc60c2893
;
_reflns_odcompleteness_completeness 99.93
_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:
 C1(H1A), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C13(H13A,H13B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              39643
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.860
_oxdiff_exptl_absorpt_empirical_full_min 0.371