Photoinduced Irreversible Intramolecular Proton Transfer of Arnebinones B, D, and E: The Case of Photoenolization at the <i>p</i>-Benzoquinone-CH<sub>2</sub>/CH-π System.
Yan, Hai-Wei; Zhao, Ling-Hao; Zhang, Xu; Yang, Ya-Nan; Yuan, Xiang; Zhang, Pei-Cheng; Journal of natural products 84 (2021) 2981–2989; doi:10.1021/acs.jnatprod.1c00830

data_1565506
_publ_section_title
;
 Photoinduced Irreversible Intramolecular Proton Transfer of Arnebinones
 B, D, and E: The Case of Photoenolization at the
 <i>p</i>-Benzoquinone-CH<sub>2</sub>/CH-\p System.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2981
_journal_page_last               2989
_journal_paper_doi               10.1021/acs.jnatprod.1c00830
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 O6'
_chemical_formula_sum            'C17 H16 O6'
_chemical_formula_weight         316.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-03-08
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.353(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.83225(18)
_cell_length_b                   7.31343(17)
_cell_length_c                   14.9372(4)
_cell_measurement_reflns_used    2901
_cell_measurement_temperature    112.0(10)
_cell_measurement_theta_max      70.9030
_cell_measurement_theta_min      5.9960
_cell_volume                     740.23(3)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      112.0(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.9686
_diffrn_measurement_details
;
  1 omega   -4.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000  -90.0000 74

  2 omega   -3.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000 -150.0000 26

  3 omega   38.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 52

  4 omega   71.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 26

  5 omega   59.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 26

  6 omega   44.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 71

  7 omega   42.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 49

  8 omega   45.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 53

  9 omega   40.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 50

 10 omega   55.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 49

 11 omega   47.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 42

 12 omega   64.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  120.0000 110

 13 omega   93.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 57

 14 omega   82.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  120.0000 26

 15 omega   61.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 25

 16 omega   61.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  -30.0000 25

 17 omega   77.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000 -120.0000 29

 18 omega   42.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000 -120.0000 29

 19 omega   58.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000 -180.0000 32

 20 omega  119.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 57

 21 omega   42.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 93

 22 omega   43.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000  150.0000 30

 23 omega   38.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 48

 24 omega    1.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000  150.0000 32

 25 omega  -32.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000   30.0000 85

 26 omega  -28.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  -60.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0409958000
_diffrn_orient_matrix_UB_12      -0.1853891000
_diffrn_orient_matrix_UB_13      0.0428569000
_diffrn_orient_matrix_UB_21      0.0954196000
_diffrn_orient_matrix_UB_22      0.0704614000
_diffrn_orient_matrix_UB_23      0.0925990000
_diffrn_orient_matrix_UB_31      -0.2022931000
_diffrn_orient_matrix_UB_32      0.0708310000
_diffrn_orient_matrix_UB_33      0.0200784000
_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  0.0235
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4580
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.017
_diffrn_reflns_theta_min         6.533
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93114
_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_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1204 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0489P)^2^+0.0444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                2730
_reflns_number_total             2771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00830_si_003.cif
_cod_data_source_block           exp_7041
_cod_database_code               1565506
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.883
_shelx_estimated_absorpt_t_min   0.818
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelx_res_checksum              27026
_shelx_hkl_checksum              11162