Total synthesis of Palmarumycin BGs, C1 and Guignardin E
Liu, Xinlei; Li, Shuyi; Wei, Xinyu; Zhao, Yu; Lai, Daowan; Zhou, Ligang; Wang, Mingan; RSC Advances 10 (2020) 1588–1594; doi:10.1039/C9RA10316C

data_7239878
_publ_section_title
;
 Total synthesis of Palmarumycin BGs, C1 and Guignardin E
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              1588
_journal_page_last               1594
_journal_paper_doi               10.1039/C9RA10316C
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H15 Cl O5'
_chemical_formula_sum            'C20 H15 Cl O5'
_chemical_formula_weight         370.77
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-06-13
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2019-08-17 deposited with the CCDC.	2019-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.111(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.7889(3)
_cell_length_b                   10.1048(5)
_cell_length_c                   8.8667(3)
_cell_measurement_reflns_used    3090
_cell_measurement_temperature    114(4)
_cell_measurement_theta_max      70.9870
_cell_measurement_theta_min      5.0360
_cell_volume                     786.29(5)
_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      114(4)
_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 0.9932
_diffrn_measurement_details
;
  1 omega   28.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   19.0000    0.0000 72

  2 omega   58.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   19.0000  -60.0000 30

  3 omega   39.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   37.0000  -60.0000 26

  4 omega   23.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   57.0000 -120.0000 31

  5 omega   17.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   19.0000  -60.0000 35

  6 omega    9.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   77.0000  -90.0000 42

  7 omega   76.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  178.0000    0.0000 31

  8 omega   70.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  178.0000   30.0000 27

  9 omega   81.00  107.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

 10 omega   94.00  121.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 27

 11 omega  125.00  174.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 49

 12 omega  127.00  174.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 47

 13 omega  127.00  153.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 26

 14 omega  145.00  177.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 32

 15 omega  132.00  157.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 25

 16 omega  124.00  167.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 43

 17 omega  118.00  176.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 58

 18 omega  100.00  125.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 25

 19 omega   91.00  117.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -120.0000 26

 20 omega   90.00  116.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 26

 21 omega   88.00  120.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 32

 22 omega   90.00  122.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 32

 23 omega   88.00  127.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 39

 24 omega  108.00  164.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 56

 25 omega   91.00  116.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 25

 26 omega   90.00  117.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 27

 27 omega   88.00  114.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 26

 28 omega   88.00  114.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 26

 29 omega   82.00  107.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 25

 30 omega   81.00  108.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 27

 31 omega   81.00  107.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 32 omega   82.00  107.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 25

 33 omega   93.00  118.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 25

 34 omega   74.00   99.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 25

 35 omega   70.00   96.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 26

 36 omega   70.00   96.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 26

 37 omega   46.00   91.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 45

 38 omega   49.00  126.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 77

 39 omega   40.00   74.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 34

 40 omega   39.00   98.00   1.0000    1.6000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 59

 41 omega   -3.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -99.0000 -180.0000 31

 42 omega  -30.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -37.0000  -90.0000 71

 43 omega  -31.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -37.0000 -180.0000 71

 44 omega  -31.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -57.0000   60.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1283194000
_diffrn_orient_matrix_UB_12      0.0024699000
_diffrn_orient_matrix_UB_13      -0.1254734000
_diffrn_orient_matrix_UB_21      -0.1137584000
_diffrn_orient_matrix_UB_22      -0.0503239000
_diffrn_orient_matrix_UB_23      0.1131670000
_diffrn_orient_matrix_UB_31      -0.0374905000
_diffrn_orient_matrix_UB_32      0.1438767000
_diffrn_orient_matrix_UB_33      0.0416669000
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6127
_diffrn_reflns_theta_full        71.17
_diffrn_reflns_theta_max         71.17
_diffrn_reflns_theta_min         5.04
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.434
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79867
_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    1.566
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.0990
_reflns_number_gt                2626
_reflns_number_total             2729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ra10316c2.cif
_cod_data_source_block           exp_6109
_cod_depositor_comments          'Adding full bibliography for 7239878.cif.'
_cod_original_cell_volume        786.30(6)
_cod_database_code               7239878
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97