Convergent Synthesis of Tetrahydropyranyl Side Chain of Verucopeptin, an Antitumor Antibiotic Active against Multidrug-resistant Cancers
Sun, Yuanjun; Tang, Wenhao; Ni, Huxin; Wang, Mei; Huang, Bin; Long, Yaqiu; Chemical Communications  (2022) –; doi:10.1039/D2CC04529J

data_7130950
_publ_section_title
;
 Convergent Synthesis of Tetrahydropyranyl Side Chain of Verucopeptin, an
 Antitumor Antibiotic Active against Multidrug-resistant Cancers
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04529J
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H23 Cl4 N O10'
_chemical_formula_sum            'C23 H23 Cl4 N O10'
_chemical_formula_weight         615.22
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-05-30 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1465(3)
_cell_length_b                   8.8611(3)
_cell_length_c                   38.0503(12)
_cell_measurement_reflns_used    4060
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      77.3
_cell_measurement_theta_min      4.6
_cell_volume                     2746.74(16)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) 
(compiled Aug  2 2013,16:46:58) 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) 
(compiled Aug  2 2013,16:46:58) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) 
(compiled Aug  2 2013,16:46:58) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_unetI/netI     0.1157
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            12532
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.381
_diffrn_reflns_theta_min         4.648
_exptl_absorpt_coefficient_mu    4.406
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET) 
(compiled Aug  2 2013,16:46:58) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.115
_refine_ls_abs_structure_details
; 
 Flack x determined using 1471 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.015(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         5481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0753
_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^)+(0.0010P)^2^+4.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1614
_refine_ls_wR_factor_ref         0.1782
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                4637
_reflns_number_total             5481
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04529j2.cif
_cod_data_source_block           HuangB-6
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

data item '_atom_sites_solution_primary' value 'direct method' was
changed to 'direct'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130950
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              78341
_shelx_hkl_checksum              28064