Total synthesis, structure revision and cytotoxic activity of Sch 53825 and its derivatives
Xu, Leichuan; Ma, Haoyun; An, Xinkun; Li, Yihao; Zhang, Qian; Liu, Xinlei; Wang, Mingan; RSC Advances 12 (2022) 17629–17636; doi:10.1039/D2RA02898K

data_7245075
_publ_section_title
;
 Total synthesis, structure revision and cytotoxic activity of Sch 53825
 and its derivatives
;
_journal_issue                   27
_journal_name_full               'RSC Advances'
_journal_page_first              17629
_journal_page_last               17636
_journal_paper_doi               10.1039/D2RA02898K
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H13 Cl O5'
_chemical_formula_sum            'C20 H13 Cl O5'
_chemical_formula_weight         368.75
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-04-27
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2022-04-28 deposited with the CCDC.	2022-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.15545(11)
_cell_length_b                   11.6040(2)
_cell_length_c                   25.9405(5)
_cell_measurement_reflns_used    3226
_cell_measurement_temperature    117.65(10)
_cell_measurement_theta_max      71.1370
_cell_measurement_theta_min      3.4170
_cell_volume                     1551.86(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      117.65(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9770
_diffrn_measurement_details
;
  1 omega  -37.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -19.0000   60.0000 64

  2 omega    7.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036  -99.0000   60.0000 56

  3 omega   16.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   77.0000   90.0000 58

  4 omega  102.00  168.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 66

  5 omega  124.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 51

  6 omega  150.00  175.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 25

  7 omega   91.00  121.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 30

  8 omega   64.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 26

  9 omega   53.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 38

 10 omega   45.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 48

 11 omega   47.00   88.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 41

 12 omega   38.00   77.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 39

 13 omega   40.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 14 omega   40.00  105.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 65

 15 omega   39.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.8036   19.0000 -150.0000 60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0654012000
_diffrn_orient_matrix_UB_12      0.1025219000
_diffrn_orient_matrix_UB_13      -0.0354314000
_diffrn_orient_matrix_UB_21      0.2862920000
_diffrn_orient_matrix_UB_22      -0.0380342000
_diffrn_orient_matrix_UB_23      -0.0011151000
_diffrn_orient_matrix_UB_31      -0.0554754000
_diffrn_orient_matrix_UB_32      -0.0752971000
_diffrn_orient_matrix_UB_33      -0.0476353000
_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  0.0330
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5497
_diffrn_reflns_theta_full        71.13
_diffrn_reflns_theta_max         71.13
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89438
_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    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3-MeOH'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0605P)^2^+0.1132P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                2821
_reflns_number_total             2944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ra02898k2.cif
_cod_data_source_block           exp_8018
_cod_database_code               7245075
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97