#------------------------------------------------------------------------------
#$Date: 2016-02-17 15:58:20 +0200 (Wed, 17 Feb 2016) $
#$Revision: 176627 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/03/2020314.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2020314
loop_
_publ_author_name
'Pullela, Srinivas Venkata'
'Acharya, Vinod'
'Reddy, Nagarjuna'
'Harlikar, Jayvant'
'Kulkarni, Amar'
'Chavan, Rakesh'
'Yadav, Ajay'
'Manna, Shuvendu'
'Ghosh, Angshuman'
_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
(2R,3R,4R,5S)-5-Allyl-2-[(S)-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
;
CrystalClear-SM Expert (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert (Rigaku, 2014)
;
_computing_data_reduction
;
CrystalClear-SM Expert (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 et al.,  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       ω
_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 x determined using 1454 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  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/[σ²(Fo²)+(0.0405P)²+0.1659P] where P=(Fo²+2Fc²)/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     F²>2.0σ(F²)
_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
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
S S1 0.75191(7) 0.69616(6) 0.55350(2) 0.03182(14) Uani d 1
O O1 0.26736(18) 0.69593(16) 0.68646(5) 0.0270(3) Uani d 1
O O2 -0.16817(19) 0.34917(19) 0.72260(6) 0.0327(4) Uani d 1
H H18 -0.1726 0.3074 0.7511 0.039 Uiso calc 1
O O3 0.1105(2) 0.3635(2) 0.79208(5) 0.0328(4) Uani d 1
H H19 0.1752 0.2837 0.7923 0.039 Uiso calc 1
O O4 0.64460(18) 0.61630(18) 0.70728(5) 0.0284(3) Uani d 1
H H20 0.7053 0.5376 0.7149 0.034 Uiso calc 1
O O5 0.8699(2) 0.6311(2) 0.58990(7) 0.0467(5) Uani d 1
O O6 0.7510(3) 0.6297(2) 0.50392(6) 0.0502(5) Uani d 1
C C1 0.3456(3) 0.5447(2) 0.68089(7) 0.0241(4) Uani d 1
H H1 0.2854 0.4884 0.6528 0.029 Uiso calc 1
C C2 0.5358(2) 0.5797(2) 0.66544(7) 0.0221(4) Uani d 1
H H2 0.5864 0.4906 0.6458 0.027 Uiso calc 1
C C3 0.5122(2) 0.7255(2) 0.63198(7) 0.0228(4) Uani d 1
H H3 0.5996 0.8075 0.6418 0.027 Uiso calc 1
C C4 0.3228(3) 0.7839(2) 0.64351(7) 0.0251(4) Uani d 1
H H4 0.2441 0.7590 0.6145 0.030 Uiso calc 1
C C5 0.3185(3) 0.4530(3) 0.72883(8) 0.0277(4) Uani d 1
H H5A 0.3862 0.5039 0.7560 0.033 Uiso calc 1
H H5B 0.3664 0.3462 0.7243 0.033 Uiso calc 1
C C6 0.1256(3) 0.4405(2) 0.74488(7) 0.0247(4) Uani d 1
H H6 0.0794 0.5494 0.7491 0.030 Uiso calc 1
C C7 0.0107(3) 0.3587(3) 0.70659(8) 0.0299(4) Uani d 1
H H7A 0.0164 0.4163 0.6745 0.036 Uiso calc 1
H H7B 0.0565 0.2517 0.7008 0.036 Uiso calc 1
C C8 0.5323(3) 0.6877(3) 0.57634(7) 0.0280(4) Uani d 1
H H8A 0.4594 0.7621 0.5569 0.034 Uiso calc 1
H H8B 0.4854 0.5813 0.5702 0.034 Uiso calc 1
C C9 0.3069(3) 0.9562(2) 0.65609(8) 0.0292(4) Uani d 1
H H9A 0.1841 0.9789 0.6662 0.035 Uiso calc 1
H H9B 0.3842 0.9801 0.6850 0.035 Uiso calc 1
C C10 0.3560(3) 1.0602(3) 0.61316(9) 0.0350(5) Uani d 1
H H10 0.2976 1.0449 0.5821 0.042 Uiso calc 1
C C11 0.4748(4) 1.1710(3) 0.61602(10) 0.0475(6) Uani d 1
H H11A 0.5353 1.1889 0.6466 0.057 Uiso calc 1
H H11B 0.5004 1.2334 0.5875 0.057 Uiso calc 1
C C12 0.7918(3) 0.8995(3) 0.54793(8) 0.0309(5) Uani d 1
C C13 0.8810(3) 0.9767(3) 0.58547(10) 0.0416(6) Uani d 1
H H13 0.9228 0.9217 0.6140 0.050 Uiso calc 1
C C14 0.9085(4) 1.1358(4) 0.58069(13) 0.0564(7) Uani d 1
H H14 0.9690 1.1911 0.6063 0.068 Uiso calc 1
C C15 0.8489(4) 1.2146(4) 0.53927(14) 0.0605(9) Uani d 1
H H15 0.8698 1.3238 0.5362 0.073 Uiso calc 1
C C16 0.7584(4) 1.1360(3) 0.50181(12) 0.0529(7) Uani d 1
H H16 0.7167 1.1915 0.4733 0.064 Uiso calc 1
C C17 0.7289(3) 0.9771(3) 0.50593(9) 0.0386(5) Uani d 1
H H17 0.6669 0.9220 0.4805 0.046 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O5 S1 O6 118.24(13)
O5 S1 C12 109.31(11)
O6 S1 C12 108.07(11)
O5 S1 C8 109.73(11)
O6 S1 C8 107.17(12)
C12 S1 C8 103.27(10)
C1 O1 C4 105.59(14)
C7 O2 H18 109.5
C6 O3 H19 109.5
C2 O4 H20 109.5
O1 C1 C5 108.84(16)
O1 C1 C2 104.07(16)
C5 C1 C2 117.17(16)
O1 C1 H1 108.8
C5 C1 H1 108.8
C2 C1 H1 108.8
O4 C2 C1 112.26(16)
O4 C2 C3 110.11(16)
C1 C2 C3 101.79(15)
O4 C2 H2 110.8
C1 C2 H2 110.8
C3 C2 H2 110.8
C8 C3 C2 112.39(17)
C8 C3 C4 110.67(16)
C2 C3 C4 104.60(15)
C8 C3 H3 109.7
C2 C3 H3 109.7
C4 C3 H3 109.7
O1 C4 C9 107.97(16)
O1 C4 C3 105.16(15)
C9 C4 C3 115.47(17)
O1 C4 H4 109.3
C9 C4 H4 109.3
C3 C4 H4 109.3
C1 C5 C6 113.76(16)
C1 C5 H5A 108.8
C6 C5 H5A 108.8
C1 C5 H5B 108.8
C6 C5 H5B 108.8
H5A C5 H5B 107.7
O3 C6 C7 109.69(17)
O3 C6 C5 110.90(15)
C7 C6 C5 113.23(17)
O3 C6 H6 107.6
C7 C6 H6 107.6
C5 C6 H6 107.6
O2 C7 C6 111.86(17)
O2 C7 H7A 109.2
C6 C7 H7A 109.2
O2 C7 H7B 109.2
C6 C7 H7B 109.2
H7A C7 H7B 107.9
C3 C8 S1 114.77(14)
C3 C8 H8A 108.6
S1 C8 H8A 108.6
C3 C8 H8B 108.6
S1 C8 H8B 108.6
H8A C8 H8B 107.5
C10 C9 C4 112.76(18)
C10 C9 H9A 109.0
C4 C9 H9A 109.0
C10 C9 H9B 109.0
C4 C9 H9B 109.0
H9A C9 H9B 107.8
C11 C10 C9 123.7(2)
C11 C10 H10 118.1
C9 C10 H10 118.1
C10 C11 H11A 120.0
C10 C11 H11B 120.0
H11A C11 H11B 120.0
C13 C12 C17 121.9(2)
C13 C12 S1 119.54(19)
C17 C12 S1 118.57(18)
C12 C13 C14 118.6(3)
C12 C13 H13 120.7
C14 C13 H13 120.7
C15 C14 C13 120.5(3)
C15 C14 H14 119.7
C13 C14 H14 119.7
C14 C15 C16 120.5(3)
C14 C15 H15 119.7
C16 C15 H15 119.7
C17 C16 C15 119.9(3)
C17 C16 H16 120.0
C15 C16 H16 120.0
C16 C17 C12 118.6(2)
C16 C17 H17 120.7
C12 C17 H17 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O5 1.4339(19)
S1 O6 1.4403(19)
S1 C12 1.769(3)
S1 C8 1.777(2)
O1 C1 1.430(3)
O1 C4 1.434(2)
O2 C7 1.426(3)
O2 H18 0.8400
O3 C6 1.426(2)
O3 H19 0.8400
O4 C2 1.424(2)
O4 H20 0.8400
C1 C5 1.514(3)
C1 C2 1.531(3)
C1 H1 1.0000
C2 C3 1.543(3)
C2 H2 1.0000
C3 C8 1.528(3)
C3 C4 1.554(3)
C3 H3 1.0000
C4 C9 1.514(3)
C4 H4 1.0000
C5 C6 1.530(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.515(3)
C6 H6 1.0000
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.497(3)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.310(4)
C10 H10 0.9500
C11 H11A 0.9500
C11 H11B 0.9500
C12 C13 1.378(3)
C12 C17 1.388(3)
C13 C14 1.381(4)
C13 H13 0.9500
C14 C15 1.371(5)
C14 H14 0.9500
C15 C16 1.387(5)
C15 H15 0.9500
C16 C17 1.380(4)
C16 H16 0.9500
C17 H17 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H18 O1 4_546 0.840 2.051 2.859(3) 161.2 no
O2 H18 O3 . 0.840 2.460 2.817(3) 106.6 no
O3 H19 O4 4_646 0.840 1.979 2.813(3) 172.0 no
O4 H20 O2 1_655 0.840 1.886 2.719(3) 171.4 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 O1 C1 C5 170.74(15)
C4 O1 C1 C2 45.09(18)
O1 C1 C2 O4 81.59(18)
C5 C1 C2 O4 -38.6(2)
O1 C1 C2 C3 -36.12(18)
C5 C1 C2 C3 -156.31(17)
O4 C2 C3 C8 135.57(17)
C1 C2 C3 C8 -105.19(17)
O4 C2 C3 C4 -104.31(17)
C1 C2 C3 C4 14.93(19)
C1 O1 C4 C9 -158.33(16)
C1 O1 C4 C3 -34.53(19)
C8 C3 C4 O1 131.96(18)
C2 C3 C4 O1 10.70(19)
C8 C3 C4 C9 -109.15(19)
C2 C3 C4 C9 129.58(18)
O1 C1 C5 C6 55.3(2)
C2 C1 C5 C6 172.89(17)
C1 C5 C6 O3 -175.56(17)
C1 C5 C6 C7 60.6(2)
O3 C6 C7 O2 55.6(2)
C5 C6 C7 O2 -179.89(16)
C2 C3 C8 S1 -87.49(19)
C4 C3 C8 S1 155.97(15)
O5 S1 C8 C3 39.8(2)
O6 S1 C8 C3 169.40(16)
C12 S1 C8 C3 -76.62(18)
O1 C4 C9 C10 -178.13(17)
C3 C4 C9 C10 64.6(2)
C4 C9 C10 C11 -125.5(3)
O5 S1 C12 C13 -18.8(2)
O6 S1 C12 C13 -148.67(19)
C8 S1 C12 C13 98.00(19)
O5 S1 C12 C17 162.38(17)
O6 S1 C12 C17 32.5(2)
C8 S1 C12 C17 -80.87(19)
C17 C12 C13 C14 -0.2(4)
S1 C12 C13 C14 -179.1(2)
C12 C13 C14 C15 -0.4(4)
C13 C14 C15 C16 0.8(4)
C14 C15 C16 C17 -0.5(4)
C15 C16 C17 C12 -0.1(4)
C13 C12 C17 C16 0.5(3)
S1 C12 C17 C16 179.33(18)
