Structural corroboration of two important building blocks of the anticancer drug eribulin mesylate through two-dimensional NMR and single-crystal X-ray diffraction studies
Pullela, Srinivas Venkata; Acharya, Vinod; Reddy, Nagarjuna; Harlikar, Jayvant; Kulkarni, Amar; Chavan, Rakesh; Yadav, Ajay; Manna, Shuvendu; Ghosh, Angshuman; Acta Crystallographica Section C 72 (2016) 14–20; doi:10.1107/S2053229615022305

data_2020314
_publ_section_title
;
 Structural corroboration of two important building blocks of the
 anticancer drug eribulin mesylate through two-dimensional NMR and
 single-crystal X-ray diffraction studies
;
_journal_coeditor_code           FN3209
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              14
_journal_page_last               20
_journal_paper_doi               10.1107/S2053229615022305
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C17 H24 O6 S'
_chemical_formula_moiety         'C17 H24 O6 S'
_chemical_formula_sum            'C17 H24 O6 S'
_chemical_formula_weight         356.43
_chemical_name_systematic
(2<i>R</i>,3<i>R</i>,4<i>R</i>,5<i>S</i>)-5-Allyl-2-[(<i>S</i>)-2,3-dihydroxypropyl]-4-[(phenylsulfonyl)methyl]tetrahydrofuran-3-ol
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.593(6)
_cell_length_b                   8.542(7)
_cell_length_c                   26.70(2)
_cell_measurement_reflns_used    4380
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     1732(2)
_computing_cell_refinement
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2014)
;
_computing_data_collection
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2014)
;
_computing_data_reduction
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2014)
;
_computing_molecular_graphics
;
CrystalStructure (Rigaku, 2015)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1994)
;
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 13.653
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14279
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         3.052
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Rigaku, 1999)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             760.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1454 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.1659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                3733
_reflns_number_total             3942
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            fn3209sup1.cif
_cod_data_source_block           Comp_XV
_cod_depositor_comments
;Adding full bibliography for 2020313--2020314.cif.

 Adding full bibliography for 2020313--2020314.cif.
;
_cod_database_code               2020314
_cod_database_fobs_code          2020314
_shelx_hkl_checksum              10160
_shelx_res_checksum              99880