Burchellin and its stereoisomers: total synthesis, structural elucidation and antiviral activity
Wang, Ru-Bing; Ren, Xiao-Dong; He, Jie; Zhu, Shan-Shan; Xie, Hui-Ru; Su, Guo-Zhu; Ma, Shuang-Gang; Yu, Shi-Shan; Organic & Biomolecular Chemistry 18 (2020) 9081–9087; doi:10.1039/D0OB01889A

data_7157762
_publ_section_title
;
 Burchellin and its stereoisomers: total synthesis, structural elucidation
 and antiviral activity
;
_journal_issue                   44
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              9081
_journal_page_last               9087
_journal_paper_doi               10.1039/D0OB01889A
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C26 H21 Br O5'
_chemical_formula_sum            'C26 H21 Br O5'
_chemical_formula_weight         493.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc23lzk8
_audit_creation_date             2019-09-17
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2019-09-19 deposited with the CCDC.	2020-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.857(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6835(5)
_cell_length_b                   10.2297(4)
_cell_length_c                   18.6723(4)
_cell_measurement_reflns_used    3564
_cell_measurement_temperature    109.4(2)
_cell_measurement_theta_max      70.9480
_cell_measurement_theta_min      4.3090
_cell_volume                     2184.07(14)
_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      109.4(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9794
_diffrn_measurement_details
;
  1 omega    8.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000    0.0000 45

  2 omega   13.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000   90.0000 48

  3 omega   54.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -178.0000   60.0000 55

  4 omega   45.00  127.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 82

  5 omega   79.00  106.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 27

  6 omega   47.00   76.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 29

  7 omega   39.00   82.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 43

  8 omega   40.00   69.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 29

  9 omega   94.00  151.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 57

 10 omega  128.00  154.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

 11 omega  100.00  178.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 78

 12 omega   79.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000    0.0000 27

 13 omega   20.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000 -180.0000 83

 14 omega   -4.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000 -150.0000 46

 15 omega   41.00   98.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 57

 16 omega   38.00   91.00   1.0000    1.3000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -34.0000  110.0000 53

 17 omega   22.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  120.0000 46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0491274000
_diffrn_orient_matrix_UB_12      0.1160568000
_diffrn_orient_matrix_UB_13      0.0367787000
_diffrn_orient_matrix_UB_21      -0.1078794000
_diffrn_orient_matrix_UB_22      -0.0819950000
_diffrn_orient_matrix_UB_23      0.0065737000
_diffrn_orient_matrix_UB_31      0.0641702000
_diffrn_orient_matrix_UB_32      -0.0496081000
_diffrn_orient_matrix_UB_33      0.0756182000
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8013
_diffrn_reflns_theta_full        70.95
_diffrn_reflns_theta_max         70.95
_diffrn_reflns_theta_min         4.12
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77077
_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_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.9723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                3606
_reflns_number_total             4123
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob01889a2.cif
_cod_data_source_block           exp_6164
_cod_original_cell_volume        2184.09(13)
_cod_database_code               7157762
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97