#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/09/4030929.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4030929
loop_
_publ_author_name
'Hansen, Steen U.'
'Dalton, Charlotte E.'
'Baráth, Marek'
'Kwan, Glenn'
'Raftery, James'
'Jayson, Gordon C.'
'Miller, Gavin J.'
'Gardiner, John M.'
_publ_section_title
;
 Synthesis of l-Iduronic Acid Derivatives via [3.2.1] and [2.2.2]
 l-Iduronic Lactones from Bulk Glucose-Derived Cyanohydrin Hydrolysis: A
 Reversible Conformationally Switched Superdisarmed/Rearmed Lactone Route
 to Heparin Disaccharides.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3777
_journal_page_last               3789
_journal_paper_doi               10.1021/jo502776f
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H22 O6 S'
_chemical_formula_weight         462.50
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5965(9)
_cell_length_b                   10.3616(9)
_cell_length_c                   22.821(2)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      72.21
_cell_measurement_theta_min      3.87
_cell_volume                     2269.2(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28155
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         72.20
_diffrn_reflns_theta_min         3.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.612
_exptl_absorpt_correction_T_max  0.8301
_exptl_absorpt_correction_T_min  0.556779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0258
_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/[σ²(Fo²)+(0.0332P)²+0.4150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0657
_reflns_number_gt                4213
_reflns_number_total             4412
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502776f_si_004.cif
_cod_data_source_block           s3663ma
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

 Adding full bibliography for 4030927--4030929.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4030929
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.62092(14) 0.56328(14) 0.21820(6) 0.0186(3) Uani 1 1 d .
H1 H 0.5795 0.4983 0.1923 0.022 Uiso 1 1 calc R
C2 C 0.68193(14) 0.67266(14) 0.18228(6) 0.0189(3) Uani 1 1 d .
H2 H 0.7529 0.6372 0.1559 0.023 Uiso 1 1 calc R
C3 C 0.72023(14) 0.73417(14) 0.28118(6) 0.0184(3) Uani 1 1 d .
H3 H 0.7541 0.8039 0.3064 0.022 Uiso 1 1 calc R
C4 C 0.79341(14) 0.60746(13) 0.29643(6) 0.0159(3) Uani 1 1 d .
H4 H 0.8946 0.6155 0.2918 0.019 Uiso 1 1 calc R
C5 C 0.73491(14) 0.50187(13) 0.25599(6) 0.0161(3) Uani 1 1 d .
H5 H 0.6954 0.4317 0.2795 0.019 Uiso 1 1 calc R
C6 C 0.56474(15) 0.71323(14) 0.29067(6) 0.0215(3) Uani 1 1 d .
C7 C 0.66411(15) 0.83075(15) 0.08897(7) 0.0241(3) Uani 1 1 d .
C8 C 0.70671(17) 0.95669(16) 0.09896(8) 0.0327(4) Uani 1 1 d .
H8 H 0.6725 1.0027 0.1309 0.039 Uiso 1 1 calc R
C9 C 0.80200(19) 1.01380(19) 0.06038(10) 0.0447(5) Uani 1 1 d .
H9 H 0.8315 1.0982 0.0667 0.054 Uiso 1 1 calc R
C10 C 0.85240(19) 0.9456(2) 0.01301(9) 0.0449(5) Uani 1 1 d .
H10 H 0.9159 0.9841 -0.0123 0.054 Uiso 1 1 calc R
C11 C 0.80939(19) 0.8209(2) 0.00300(8) 0.0409(5) Uani 1 1 d .
H11 H 0.8439 0.7753 -0.0289 0.049 Uiso 1 1 calc R
C12 C 0.71427(16) 0.76329(18) 0.04067(7) 0.0303(3) Uani 1 1 d .
H12 H 0.6841 0.6795 0.0336 0.036 Uiso 1 1 calc R
C13 C 0.82742(15) 0.63741(14) 0.39865(6) 0.0208(3) Uani 1 1 d .
C14 C 0.76539(16) 0.61291(14) 0.45700(6) 0.0208(3) Uani 1 1 d .
C15 C 0.63486(16) 0.55477(15) 0.46247(7) 0.0240(3) Uani 1 1 d .
H15 H 0.5874 0.5269 0.4293 0.029 Uiso 1 1 calc R
C16 C 0.57601(18) 0.53865(17) 0.51749(7) 0.0292(4) Uani 1 1 d .
H16 H 0.4880 0.5020 0.5211 0.035 Uiso 1 1 calc R
C17 C 0.64821(18) 0.57699(16) 0.56684(7) 0.0304(4) Uani 1 1 d .
H17 H 0.6092 0.5646 0.6037 0.036 Uiso 1 1 calc R
C18 C 0.77806(19) 0.63374(16) 0.56183(7) 0.0306(4) Uani 1 1 d .
H18 H 0.8264 0.6587 0.5953 0.037 Uiso 1 1 calc R
C19 C 0.83621(18) 0.65343(15) 0.50679(7) 0.0272(3) Uani 1 1 d .
H19 H 0.9224 0.6937 0.5033 0.033 Uiso 1 1 calc R
C20 C 0.94791(15) 0.38315(14) 0.24153(6) 0.0216(3) Uani 1 1 d .
H20A H 1.0071 0.4443 0.2619 0.026 Uiso 1 1 calc R
H20B H 1.0027 0.3443 0.2105 0.026 Uiso 1 1 calc R
C21 C 0.90401(14) 0.27923(13) 0.28384(6) 0.0180(3) Uani 1 1 d .
C22 C 0.95268(16) 0.27996(15) 0.34105(7) 0.0246(3) Uani 1 1 d .
H22 H 1.0119 0.3455 0.3535 0.030 Uiso 1 1 calc R
C23 C 0.91364(18) 0.18369(18) 0.37982(7) 0.0331(4) Uani 1 1 d .
H23 H 0.9479 0.1841 0.4179 0.040 Uiso 1 1 calc R
C24 C 0.82378(17) 0.08679(16) 0.36202(8) 0.0330(4) Uani 1 1 d .
H24 H 0.7977 0.0220 0.3880 0.040 Uiso 1 1 calc R
C25 C 0.77301(16) 0.08695(15) 0.30523(8) 0.0286(4) Uani 1 1 d .
H25 H 0.7115 0.0228 0.2933 0.034 Uiso 1 1 calc R
C26 C 0.81330(15) 0.18198(14) 0.26620(7) 0.0228(3) Uani 1 1 d .
H26 H 0.7796 0.1809 0.2280 0.027 Uiso 1 1 calc R
O1 O 0.74734(10) 0.76356(10) 0.22112(4) 0.0211(2) Uani 1 1 d .
O2 O 0.51559(10) 0.61530(10) 0.25745(4) 0.0208(2) Uani 1 1 d .
O3 O 0.49104(11) 0.77046(11) 0.32399(5) 0.0309(3) Uani 1 1 d .
O4 O 0.75765(10) 0.57385(9) 0.35563(4) 0.0172(2) Uani 1 1 d .
O5 O 0.92572(12) 0.70626(12) 0.38883(5) 0.0338(3) Uani 1 1 d .
O6 O 0.83271(10) 0.45169(10) 0.21581(4) 0.0200(2) Uani 1 1 d .
S1 S 0.54799(3) 0.75143(4) 0.138262(16) 0.02486(9) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables 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
O2 C1 C2 108.92(11)
O2 C1 C5 107.68(11)
C2 C1 C5 109.83(11)
O2 C1 H1 110.1
C2 C1 H1 110.1
C5 C1 H1 110.1
O1 C2 C1 108.96(11)
O1 C2 S1 110.74(9)
C1 C2 S1 111.10(10)
O1 C2 H2 108.7
C1 C2 H2 108.7
S1 C2 H2 108.7
O1 C3 C6 110.20(11)
O1 C3 C4 108.53(11)
C6 C3 C4 107.17(11)
O1 C3 H3 110.3
C6 C3 H3 110.3
C4 C3 H3 110.3
O4 C4 C3 108.20(11)
O4 C4 C5 107.74(10)
C3 C4 C5 107.87(11)
O4 C4 H4 111.0
C3 C4 H4 111.0
C5 C4 H4 111.0
O6 C5 C1 105.19(11)
O6 C5 C4 114.16(11)
C1 C5 C4 107.65(11)
O6 C5 H5 109.9
C1 C5 H5 109.9
C4 C5 H5 109.9
O3 C6 O2 121.50(13)
O3 C6 C3 126.80(14)
O2 C6 C3 111.66(12)
C8 C7 C12 120.07(16)
C8 C7 S1 120.94(13)
C12 C7 S1 118.97(13)
C7 C8 C9 119.13(18)
C7 C8 H8 120.4
C9 C8 H8 120.4
C10 C9 C8 120.34(18)
C10 C9 H9 119.8
C8 C9 H9 119.8
C11 C10 C9 120.43(18)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 119.90(19)
C10 C11 H11 120.1
C12 C11 H11 120.1
C11 C12 C7 120.12(18)
C11 C12 H12 119.9
C7 C12 H12 119.9
O5 C13 O4 122.60(13)
O5 C13 C14 125.75(14)
O4 C13 C14 111.63(12)
C19 C14 C15 119.77(14)
C19 C14 C13 119.15(14)
C15 C14 C13 121.03(13)
C16 C15 C14 119.90(15)
C16 C15 H15 120.0
C14 C15 H15 120.0
C17 C16 C15 119.97(15)
C17 C16 H16 120.0
C15 C16 H16 120.0
C16 C17 C18 120.48(15)
C16 C17 H17 119.8
C18 C17 H17 119.8
C17 C18 C19 119.94(15)
C17 C18 H18 120.0
C19 C18 H18 120.0
C14 C19 C18 119.91(16)
C14 C19 H19 120.0
C18 C19 H19 120.0
O6 C20 C21 113.54(11)
O6 C20 H20A 108.9
C21 C20 H20A 108.9
O6 C20 H20B 108.9
C21 C20 H20B 108.9
H20A C20 H20B 107.7
C22 C21 C26 119.16(14)
C22 C21 C20 120.36(13)
C26 C21 C20 120.48(13)
C23 C22 C21 120.43(15)
C23 C22 H22 119.8
C21 C22 H22 119.8
C24 C23 C22 120.22(15)
C24 C23 H23 119.9
C22 C23 H23 119.9
C23 C24 C25 119.54(15)
C23 C24 H24 120.2
C25 C24 H24 120.2
C26 C25 C24 120.36(15)
C26 C25 H25 119.8
C24 C25 H25 119.8
C25 C26 C21 120.28(14)
C25 C26 H26 119.9
C21 C26 H26 119.9
C3 O1 C2 111.87(10)
C6 O2 C1 112.41(11)
C13 O4 C4 116.38(11)
C5 O6 C20 115.31(10)
C7 S1 C2 96.50(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.4542(17)
C1 C2 1.516(2)
C1 C5 1.5314(19)
C1 H1 0.9800
C2 O1 1.4376(17)
C2 S1 1.8242(14)
C2 H2 0.9800
C3 O1 1.4279(16)
C3 C6 1.523(2)
C3 C4 1.5290(19)
C3 H3 0.9800
C4 O4 1.4368(16)
C4 C5 1.5374(19)
C4 H4 0.9800
C5 O6 1.4115(16)
C5 H5 0.9800
C6 O3 1.1960(18)
C6 O2 1.3516(18)
C7 C8 1.386(2)
C7 C12 1.391(2)
C7 S1 1.7839(16)
C8 C9 1.401(3)
C8 H8 0.9300
C9 C10 1.379(3)
C9 H9 0.9300
C10 C11 1.375(3)
C10 H10 0.9300
C11 C12 1.389(2)
C11 H11 0.9300
C12 H12 0.9300
C13 O5 1.2038(18)
C13 O4 1.3588(17)
C13 C14 1.480(2)
C14 C19 1.389(2)
C14 C15 1.396(2)
C15 C16 1.387(2)
C15 H15 0.9300
C16 C17 1.381(2)
C16 H16 0.9300
C17 C18 1.383(3)
C17 H17 0.9300
C18 C19 1.390(2)
C18 H18 0.9300
C19 H19 0.9300
C20 O6 1.4391(17)
C20 C21 1.507(2)
C20 H20A 0.9700
C20 H20B 0.9700
C21 C22 1.387(2)
C21 C26 1.391(2)
C22 C23 1.385(2)
C22 H22 0.9300
C23 C24 1.384(3)
C23 H23 0.9300
C24 C25 1.385(3)
C24 H24 0.9300
C25 C26 1.383(2)
C25 H25 0.9300
C26 H26 0.9300
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
O2 C1 C2 O1 61.67(13)
C5 C1 C2 O1 -56.03(14)
O2 C1 C2 S1 -60.60(13)
C5 C1 C2 S1 -178.30(9)
O1 C3 C4 O4 -176.00(10)
C6 C3 C4 O4 -57.00(13)
O1 C3 C4 C5 -59.70(13)
C6 C3 C4 C5 59.30(13)
O2 C1 C5 O6 179.20(10)
C2 C1 C5 O6 -62.33(14)
O2 C1 C5 C4 -58.70(13)
C2 C1 C5 C4 59.77(14)
O4 C4 C5 O6 -129.76(11)
C3 C4 C5 O6 113.64(12)
O4 C4 C5 C1 113.87(11)
C3 C4 C5 C1 -2.72(14)
O1 C3 C6 O3 -122.66(16)
C4 C3 C6 O3 119.42(16)
O1 C3 C6 O2 59.55(15)
C4 C3 C6 O2 -58.37(14)
C12 C7 C8 C9 -0.9(2)
S1 C7 C8 C9 177.64(12)
C7 C8 C9 C10 0.2(2)
C8 C9 C10 C11 0.2(3)
C9 C10 C11 C12 0.2(3)
C10 C11 C12 C7 -1.0(2)
C8 C7 C12 C11 1.4(2)
S1 C7 C12 C11 -177.26(12)
O5 C13 C14 C19 -11.4(2)
O4 C13 C14 C19 169.90(13)
O5 C13 C14 C15 165.97(16)
O4 C13 C14 C15 -12.76(19)
C19 C14 C15 C16 0.5(2)
C13 C14 C15 C16 -176.82(14)
C14 C15 C16 C17 -1.7(2)
C15 C16 C17 C18 1.2(3)
C16 C17 C18 C19 0.5(2)
C15 C14 C19 C18 1.2(2)
C13 C14 C19 C18 178.60(14)
C17 C18 C19 C14 -1.7(2)
O6 C20 C21 C22 -123.64(14)
O6 C20 C21 C26 55.82(17)
C26 C21 C22 C23 1.3(2)
C20 C21 C22 C23 -179.28(14)
C21 C22 C23 C24 -1.0(2)
C22 C23 C24 C25 -0.1(2)
C23 C24 C25 C26 1.0(2)
C24 C25 C26 C21 -0.8(2)
C22 C21 C26 C25 -0.4(2)
C20 C21 C26 C25 -179.84(13)
C6 C3 O1 C2 -49.81(15)
C4 C3 O1 C2 67.26(13)
C1 C2 O1 C3 -7.72(15)
S1 C2 O1 C3 114.78(10)
O3 C6 O2 C1 177.36(13)
C3 C6 O2 C1 -4.71(15)
C2 C1 O2 C6 -53.82(14)
C5 C1 O2 C6 65.24(14)
O5 C13 O4 C4 -9.0(2)
C14 C13 O4 C4 169.77(11)
C3 C4 O4 C13 -78.88(13)
C5 C4 O4 C13 164.75(11)
C1 C5 O6 C20 -177.26(11)
C4 C5 O6 C20 64.96(15)
C21 C20 O6 C5 52.03(16)
C8 C7 S1 C2 -94.35(13)
C12 C7 S1 C2 84.25(12)
O1 C2 S1 C7 75.93(10)
C1 C2 S1 C7 -162.83(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139094195
