Dibenzoate esters of <i>cis</i>-tetralin-2,3-diol as analogs of (–)-epigallocatechin gallate: synthesis and crystal structure of anticancer drug candidates
Rutherford, Ryan Noboru; Ura, Shinji; Chan, Tak-Hang; Fukumoto, Kozo; Nishioka, Takanori; Renzetti, Andrea; Acta Crystallographica Section C 76 (2020) –; doi:10.1107/S2053229620014916

data_2022277
_publ_section_title
;
 Dibenzoate esters of <i>cis</i>-tetralin-2,3-diol as analogs of
 (--)-epigallocatechin gallate: synthesis and crystal structure of
 anticancer drug candidates
;
_journal_coeditor_code           OP3007
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620014916
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C66 H56 O10'
_chemical_formula_moiety         'C66 H56 O10'
_chemical_formula_sum            'C66 H56 O10'
_chemical_formula_weight         1009.10
_chemical_name_systematic
;
(2<i>R</i>,3<i>S</i>)-1,2,3,4-Tetrahydronaphthalene-2,3-diyl
bis[3,4,5-tris(benzyloxy)benzoate]
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                79.013(6)
_cell_angle_beta                 87.544(9)
_cell_angle_gamma                83.381(8)
_cell_formula_units_Z            2
_cell_length_a                   13.574(3)
_cell_length_b                   13.829(3)
_cell_length_c                   14.657(3)
_cell_measurement_reflns_used    8135
_cell_measurement_temperature    193.4
_cell_measurement_theta_max      27.4662
_cell_measurement_theta_min      3.0193
_cell_volume                     2682.3(10)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2008)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2008)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2008)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>, 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>, 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      193.4
_diffrn_detector                 CCD
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device       'AFC10: Fixed Chi 2 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22437
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_min         3.019
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2008)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       plate
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     740
_refine_ls_number_reflns         11802
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0587P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                7475
_reflns_number_total             11802
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            op3007sup1.cif
_cod_data_source_block           4
_cod_database_code               2022277
_cod_database_fobs_code          2022277
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.995
_shelx_hkl_checksum              1059
_shelx_res_checksum              67383