# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1843444'
_audit_update_record             
;
2018-05-15 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_5                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01123 Ang.
RESPONSE: The overall quality of the data may be poor due to the crystal quality
;
# Added during the CSD deposition process: Tuesday 15 May 2018 07:56 PM
# end Validation Reply Form

#exp_code: JF76-253_1811_s0-86a

_audit_creation_date             2015-10-10T17:21:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
3,6-Anhydro-2-deoxy-5,7-di-O-methyl-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone
_chemical_name_common            
3,6-Anhydro-2-deoxy-5,7-di-O-methyl-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone
_chemical_formula_moiety         'C15 H18 O5'
_chemical_formula_sum            'C15 H18 O5'
_chemical_formula_weight         278.29
_chemical_melting_point          369
_chemical_compound_source        synthetic
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
        They are only intended as comments.
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.2861(10)
_cell_length_b                   9.8316(10)
_cell_length_c                   18.092(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1473.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1137
_cell_measurement_theta_min      3.331
_cell_measurement_theta_max      23.051
_cell_oxdiff_length_a            8.2802(17)
_cell_oxdiff_length_b            9.8294(11)
_cell_oxdiff_length_c            18.1090(19)
_cell_oxdiff_angle_alpha         89.897(9)
_cell_oxdiff_angle_beta          90.143(12)
_cell_oxdiff_angle_gamma         89.996(12)
_cell_oxdiff_volume              1473.9(4)
_cell_oxdiff_measurement_reflns_used 1137

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 3 0.2029
0 -5 -3 0.1659
5 -2 -2 0.2578
-1 1 0 0.206
5 -1 1 0.2678
-5 0 -2 0.3333
0 0 26 0.0139
5 4 1 0.3447
0 2 -25 0.0313
1 1 -45 0.0147
0 0 -26 0.0279
-1 -1 45 0.0287


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)

 Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid
 (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897), followed by
 empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.995

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Oxford Diffraction)'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Sapphire3 (Oxford Diffraction)'
_diffrn_detector_area_resol_mean 16.328
_diffrn_orient_matrix_ub_11      -0.0413103
_diffrn_orient_matrix_ub_12      -0.0554914
_diffrn_orient_matrix_ub_13      0.0164407
_diffrn_orient_matrix_ub_21      0.068585
_diffrn_orient_matrix_ub_22      -0.0419505
_diffrn_orient_matrix_ub_23      -0.0055678
_diffrn_orient_matrix_ub_31      0.030456
_diffrn_orient_matrix_ub_32      0.0191865
_diffrn_orient_matrix_ub_33      0.0351125
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_reflns_av_R_equivalents  0.124
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_number            4375
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.704
_diffrn_reflns_theta_max         24.404
_diffrn_reflns_theta_full        24.404
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_Friedel_coverage         0.712
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_number_total             2428
_reflns_number_gt                1631
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_shelx_SHELXL_version_number     2014/7
_computing_molecular_graphics    'Mercury CSD (Macrae et al., 2008)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1484P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       6.3(6)
_refine_ls_number_reflns         2428
_refine_ls_number_parameters     183
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.1193
_refine_ls_wR_factor_ref         0.268
_refine_ls_wR_factor_gt          0.237
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
; The absolute structure parameter is meaningless because the compound is a 
 weak anomalous scatterer.

#_refine_ls_abs_structure_details
#;
# Flack x determined using 452 quotients [(I+)-(I-)]/[(I+)+(I-)]
# (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
#;
#_refine_ls_abs_structure_Flack          -0.7(10)
;
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.165

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0367(10) 0.4243(9) 0.3027(4) 0.170(3) Uani 1 1 d . . . . .
O2 O 0.7859(8) 0.4618(6) 0.3404(2) 0.1188(19) Uani 1 1 d D . . . .
O3 O 0.4761(6) 0.4585(5) 0.4810(2) 0.1087(18) Uani 1 1 d . . . . .
O4 O 0.7949(8) 0.3510(5) 0.5003(2) 0.123(2) Uani 1 1 d . . . . .
O5 O 0.6796(5) 0.6744(4) 0.5732(2) 0.1045(18) Uani 1 1 d . . . . .
C1 C 0.9214(14) 0.3879(11) 0.3399(5) 0.129(3) Uani 1 1 d . . . . .
C15 C 0.6022(11) 0.7231(9) 0.6350(6) 0.142(3) Uani 1 1 d . . . . .
H15A H 0.6704 0.7112 0.6774 0.213 Uiso 1 1 calc R U . . .
H15B H 0.5033 0.6741 0.6422 0.213 Uiso 1 1 calc R U . . .
H15C H 0.579 0.8181 0.6286 0.213 Uiso 1 1 calc R U . . .
C2 C 0.9014(12) 0.2633(7) 0.3861(4) 0.124(3) Uani 1 1 d . . . . .
H2A H 0.994 0.2497 0.418 0.148 Uiso 1 1 calc R U . . .
H2B H 0.8869 0.1833 0.3554 0.148 Uiso 1 1 calc R U . . .
C3 C 0.7516(11) 0.2929(7) 0.4306(3) 0.108(2) Uani 1 1 d . . . . .
H3 H 0.6841 0.2118 0.4366 0.129 Uiso 1 1 calc R U . . .
C4 C 0.6654(8) 0.4033(6) 0.3879(4) 0.103(2) Uani 1 1 d D . . . .
H4 H 0.5728 0.3682 0.3601 0.123 Uiso 1 1 calc R U . . .
C5 C 0.6157(8) 0.5026(6) 0.4472(4) 0.0934(19) Uani 1 1 d . . . . .
H5 H 0.6035 0.5948 0.4274 0.112 Uiso 1 1 calc R U . . .
C6 C 0.7547(8) 0.4935(6) 0.5001(3) 0.0920(19) Uani 1 1 d . . . . .
H6 H 0.846 0.5458 0.4806 0.11 Uiso 1 1 calc R U . . .
C7 C 0.7236(8) 0.5346(6) 0.5790(3) 0.0900(19) Uani 1 1 d . . . . .
H7 H 0.6324 0.4824 0.5986 0.108 Uiso 1 1 calc R U . . .
C8 C 0.8685(8) 0.5143(7) 0.6278(3) 0.097(2) Uani 1 1 d D . . . .
C9 C 1.0054(8) 0.5923(8) 0.6189(6) 0.131(3) Uani 1 1 d D . . . .
H9 H 1.0098 0.6557 0.5809 0.157 Uiso 1 1 calc R U . . .
C10 C 1.1344(11) 0.5781(12) 0.6650(7) 0.159(4) Uani 1 1 d D . . . .
H10 H 1.2218 0.6372 0.6614 0.191 Uiso 1 1 calc R U . . .
C11 C 1.1346(13) 0.4779(12) 0.7158(5) 0.155(4) Uani 1 1 d D . . . .
H11 H 1.225 0.4644 0.7454 0.186 Uiso 1 1 calc R U . . .
C12 C 1.0041(12) 0.3968(12) 0.7241(4) 0.142(4) Uani 1 1 d D . . . .
H12 H 1.0044 0.3284 0.7596 0.17 Uiso 1 1 calc R U . . .
C13 C 0.8715(10) 0.4153(9) 0.6802(3) 0.118(3) Uani 1 1 d D . . . .
H13 H 0.7821 0.3592 0.6862 0.141 Uiso 1 1 calc R U . . .
C14 C 0.3313(10) 0.4922(14) 0.4449(6) 0.153(4) Uani 1 1 d . . . . .
H14A H 0.2416 0.4573 0.4726 0.184 Uiso 1 1 calc R U . . .
H14B H 0.3224 0.5893 0.4411 0.184 Uiso 1 1 calc R U . . .
H14C H 0.3311 0.4531 0.3963 0.184 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.222(12) . ?
O2 C1 1.337(11) . ?
O2 C4 1.437(7) . ?
O3 C5 1.379(8) . ?
O3 C14 1.406(9) . ?
O4 C3 1.429(8) . ?
O4 C6 1.441(8) . ?
O5 C15 1.376(10) . ?
O5 C7 1.425(7) . ?
C1 C2 1.492(13) . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C2 C3 1.508(12) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C4 1.512(9) . ?
C3 H3 0.98 . ?
C4 C5 1.508(10) . ?
C4 H4 0.98 . ?
C5 C6 1.501(9) . ?
C5 H5 0.98 . ?
C6 C7 1.505(9) . ?
C6 H6 0.98 . ?
C7 C8 1.504(9) . ?
C7 H7 0.98 . ?
C8 C13 1.359(11) . ?
C8 C9 1.378(8) . ?
C9 C10 1.362(8) . ?
C9 H9 0.93 . ?
C10 C11 1.348(9) . ?
C10 H10 0.93 . ?
C11 C12 1.352(9) . ?
C11 H11 0.93 . ?
C12 C13 1.368(8) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C4 111.8(6) . . ?
C5 O3 C14 115.8(5) . . ?
C3 O4 C6 109.2(4) . . ?
C15 O5 C7 113.3(6) . . ?
O1 C1 O2 120.1(10) . . ?
O1 C1 C2 129.4(11) . . ?
O2 C1 C2 110.4(9) . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C2 C3 103.4(7) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C3 C2 H2B 111.1 . . ?
H2A C2 H2B 109 . . ?
O4 C3 C2 110.0(7) . . ?
O4 C3 C4 106.4(5) . . ?
C2 C3 C4 104.7(6) . . ?
O4 C3 H3 111.8 . . ?
C2 C3 H3 111.8 . . ?
C4 C3 H3 111.8 . . ?
O2 C4 C5 110.9(5) . . ?
O2 C4 C3 105.3(6) . . ?
C5 C4 C3 103.3(5) . . ?
O2 C4 H4 112.3 . . ?
C5 C4 H4 112.3 . . ?
C3 C4 H4 112.3 . . ?
O3 C5 C6 110.0(5) . . ?
O3 C5 C4 110.0(6) . . ?
C6 C5 C4 101.9(5) . . ?
O3 C5 H5 111.5 . . ?
C6 C5 H5 111.5 . . ?
C4 C5 H5 111.5 . . ?
O4 C6 C5 103.7(5) . . ?
O4 C6 C7 107.4(5) . . ?
C5 C6 C7 117.2(6) . . ?
O4 C6 H6 109.4 . . ?
C5 C6 H6 109.4 . . ?
C7 C6 H6 109.4 . . ?
O5 C7 C8 112.1(5) . . ?
O5 C7 C6 103.5(5) . . ?
C8 C7 C6 112.6(5) . . ?
O5 C7 H7 109.5 . . ?
C8 C7 H7 109.5 . . ?
C6 C7 H7 109.5 . . ?
C13 C8 C9 117.7(7) . . ?
C13 C8 C7 121.3(6) . . ?
C9 C8 C7 121.0(7) . . ?
C10 C9 C8 121.2(9) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 119.5(10) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.4(10) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 120.0(9) . . ?
C11 C12 H12 120 . . ?
C13 C12 H12 120 . . ?
C8 C13 C12 121.0(8) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O2 C1 O1 -179.3(7) . . . . ?
C4 O2 C1 C2 2.9(8) . . . . ?
O1 C1 C2 C3 167.6(8) . . . . ?
O2 C1 C2 C3 -15.0(8) . . . . ?
C6 O4 C3 C2 107.3(7) . . . . ?
C6 O4 C3 C4 -5.6(9) . . . . ?
C1 C2 C3 O4 -93.7(7) . . . . ?
C1 C2 C3 C4 20.3(7) . . . . ?
C1 O2 C4 C5 121.5(6) . . . . ?
C1 O2 C4 C3 10.5(7) . . . . ?
O4 C3 C4 O2 97.3(7) . . . . ?
C2 C3 C4 O2 -19.1(7) . . . . ?
O4 C3 C4 C5 -19.0(8) . . . . ?
C2 C3 C4 C5 -135.5(5) . . . . ?
C14 O3 C5 C6 164.9(8) . . . . ?
C14 O3 C5 C4 -83.6(9) . . . . ?
O2 C4 C5 O3 166.1(5) . . . . ?
C3 C4 C5 O3 -81.5(6) . . . . ?
O2 C4 C5 C6 -77.2(5) . . . . ?
C3 C4 C5 C6 35.1(7) . . . . ?
C3 O4 C6 C5 28.1(8) . . . . ?
C3 O4 C6 C7 152.8(7) . . . . ?
O3 C5 C6 O4 77.7(6) . . . . ?
C4 C5 C6 O4 -38.9(6) . . . . ?
O3 C5 C6 C7 -40.3(8) . . . . ?
C4 C5 C6 C7 -157.0(5) . . . . ?
C15 O5 C7 C8 -75.9(8) . . . . ?
C15 O5 C7 C6 162.6(6) . . . . ?
O4 C6 C7 O5 -178.0(5) . . . . ?
C5 C6 C7 O5 -61.9(7) . . . . ?
O4 C6 C7 C8 60.8(7) . . . . ?
C5 C6 C7 C8 176.9(5) . . . . ?
O5 C7 C8 C13 134.1(6) . . . . ?
C6 C7 C8 C13 -109.7(7) . . . . ?
O5 C7 C8 C9 -48.3(9) . . . . ?
C6 C7 C8 C9 67.8(8) . . . . ?
C13 C8 C9 C10 -5.2(11) . . . . ?
C7 C8 C9 C10 177.2(7) . . . . ?
C8 C9 C10 C11 6.1(14) . . . . ?
C9 C10 C11 C12 -3.8(16) . . . . ?
C10 C11 C12 C13 0.7(15) . . . . ?
C9 C8 C13 C12 2.0(11) . . . . ?
C7 C8 C13 C12 179.6(7) . . . . ?
C11 C12 C13 C8 0.2(13) . . . . ?

#----------------------------------------------------------------------------#
#                   REFLECTION DATA AND REFINEMENT INSTRUCTIONS              #
#----------------------------------------------------------------------------#
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8
_database_code_depnum_ccdc_archive 'CCDC 1843449'
_audit_update_record             
;
2018-05-15 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
#exp_code: JF79-257_1816_s_a

_audit_creation_date             2015-10-09T22:49:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
3,6-Anhydro-2-deoxy-5,7-di-O-methyl-7-C-phenyl-L-glycero-D-ido-heptono-1,4-lactone
_chemical_name_common            
3,6-Anhydro-2-deoxy-5,7-di-O-methyl-7-C-phenyl-L-glycero-D-ido-heptono-1,4-lactone
_chemical_formula_moiety         'C15 H18 O5'
_chemical_formula_sum            'C15 H18 O5'
_chemical_formula_weight         278.29
_chemical_melting_point          392
_chemical_compound_source        synthetic
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
        They are only intended as comments.
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.1993(2)
_cell_length_b                   9.5498(2)
_cell_length_c                   18.6176(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1457.79(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6497
_cell_measurement_theta_min      2.395
_cell_measurement_theta_max      27.361
_cell_oxdiff_length_a            8.1993(3)
_cell_oxdiff_length_b            9.5516(3)
_cell_oxdiff_length_c            18.6139(7)
_cell_oxdiff_angle_alpha         89.979(3)
_cell_oxdiff_angle_beta          89.963(3)
_cell_oxdiff_angle_gamma         89.994(3)
_cell_oxdiff_volume              1457.78(9)
_cell_oxdiff_measurement_reflns_used 6497

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.7044
_exptl_crystal_size_mid          0.5169
_exptl_crystal_size_min          0.3677
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -3 -5 0.1838
-4 3 5 0.1838
1 0 -1 0.1724
2 1 5 0.2125
1 -1 -1 0.1911
-1 1 1 0.1911
5 3 1 0.1905
-4 2 5 0.2069
-1 -1 -1 0.2233
1 -1 1 0.2412
-1 1 -1 0.2412
-1 0 -1 0.1918
-1 -1 1 0.2458
1 1 -1 0.2458
0 0 -1 0.3197
1 5 -4 0.3068
0 1 5 0.3036


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
 
 Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid
 (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897), followed by
 empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.975

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Oxford Diffraction)'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Sapphire3 (Oxford Diffraction)'
_diffrn_detector_area_resol_mean 16.328
_diffrn_orient_matrix_ub_11      -0.0744562
_diffrn_orient_matrix_ub_12      0.0283794
_diffrn_orient_matrix_ub_13      -0.0128064
_diffrn_orient_matrix_ub_21      0.0425816
_diffrn_orient_matrix_ub_22      0.0338341
_diffrn_orient_matrix_ub_23      -0.0282805
_diffrn_orient_matrix_ub_31      -0.0112495
_diffrn_orient_matrix_ub_32      -0.0597023
_diffrn_orient_matrix_ub_33      -0.022097
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω and π scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_number            19102
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_max         29.066
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.94
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.94
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.911
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.871
_reflns_Friedel_coverage         0.688
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_number_total             3548
_reflns_number_gt                2797
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_shelx_SHELXL_version_number     2014/7
_computing_molecular_graphics    'Mercury CSD (Macrae et al., 2008)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       3.5(2)
_refine_ls_number_reflns         3548
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0973
_refine_ls_wR_factor_ref         0.2007
_refine_ls_wR_factor_gt          0.1872
_refine_ls_goodness_of_fit_ref   1.17
_refine_ls_restrained_S_all      1.17
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
; The absolute structure parameter is meaningless because the compound is a week 
 anomalous scatterer.

#_refine_ls_abs_structure_details
#;
# Flack x determined using 976 quotients [(I+)-(I-)]/[(I+)+(I-)]
# (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
#;
#_refine_ls_abs_structure_Flack          0.0(3)
;

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.178

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2362(8) 0.7816(5) 0.4860(2) 0.1522(19) Uani 1 1 d . . . . .
O2 O 0.4058(4) 0.7784(2) 0.39328(14) 0.0925(9) Uani 1 1 d . . . . .
O3 O 0.2951(3) 0.5118(3) 0.32172(12) 0.0853(8) Uani 1 1 d . . . . .
O4 O 0.5616(3) 0.6059(2) 0.23177(14) 0.0815(7) Uani 1 1 d . . . . .
O5 O 0.0827(3) 0.5033(3) 0.20734(11) 0.0808(7) Uani 1 1 d . . . . .
C1 C 0.3209(7) 0.7162(5) 0.4468(2) 0.1016(13) Uani 1 1 d . . . . .
C2 C 0.3560(7) 0.5633(5) 0.44562(18) 0.0966(12) Uani 1 1 d . . . . .
H2A H 0.2574 0.5095 0.4537 0.116 Uiso 1 1 calc R U . . .
H2B H 0.4355 0.5389 0.4821 0.116 Uiso 1 1 calc R U . . .
C3 C 0.4229(5) 0.5365(3) 0.37164(16) 0.0764(9) Uani 1 1 d . . . . .
H3 H 0.504 0.4611 0.3715 0.092 Uiso 1 1 calc R U . . .
C4 C 0.4965(4) 0.6754(3) 0.35200(18) 0.0770(9) Uani 1 1 d . . . . .
H4 H 0.614 0.6791 0.3614 0.092 Uiso 1 1 calc R U . . .
C5 C 0.4559(3) 0.6903(3) 0.27239(16) 0.0651(7) Uani 1 1 d . . . . .
H5 H 0.4549 0.7881 0.2563 0.078 Uiso 1 1 calc R U . . .
C6 C 0.2875(3) 0.6229(3) 0.27044(14) 0.0621(7) Uani 1 1 d . . . . .
H6 H 0.2066 0.6916 0.2865 0.074 Uiso 1 1 calc R U . . .
C7 C 0.2376(3) 0.5678(3) 0.19742(14) 0.0630(7) Uani 1 1 d . . . . .
H7 H 0.3164 0.4967 0.182 0.076 Uiso 1 1 calc R U . . .
C8 C 0.2311(3) 0.6827(3) 0.14195(14) 0.0626(7) Uani 1 1 d . . . . .
C9 C 0.3289(4) 0.6770(4) 0.08136(15) 0.0729(8) Uani 1 1 d . . . . .
H9 H 0.401 0.6026 0.0755 0.087 Uiso 1 1 calc R U . . .
C10 C 0.3208(6) 0.7802(5) 0.02962(19) 0.0927(12) Uani 1 1 d . . . . .
H10 H 0.3868 0.7743 -0.0109 0.111 Uiso 1 1 calc R U . . .
C11 C 0.2178(7) 0.8899(5) 0.0372(2) 0.0991(13) Uani 1 1 d . . . . .
H11 H 0.2123 0.9582 0.0017 0.119 Uiso 1 1 calc R U . . .
C12 C 0.1202(5) 0.9006(5) 0.0980(3) 0.0990(13) Uani 1 1 d . . . . .
H12 H 0.0516 0.9773 0.104 0.119 Uiso 1 1 calc R U . . .
C13 C 0.1261(4) 0.7954(4) 0.15006(19) 0.0785(8) Uani 1 1 d . . . . .
H13 H 0.0593 0.8009 0.1903 0.094 Uiso 1 1 calc R U . . .
C14 C 0.7125(6) 0.6698(7) 0.2153(5) 0.138(2) Uani 1 1 d . . . . .
H14A H 0.7429 0.6471 0.1669 0.207 Uiso 1 1 calc R U . . .
H14B H 0.7946 0.6361 0.2478 0.207 Uiso 1 1 calc R U . . .
H14C H 0.7026 0.7695 0.2201 0.207 Uiso 1 1 calc R U . . .
C15 C 0.0299(6) 0.4265(5) 0.1471(2) 0.1043(14) Uani 1 1 d . . . . .
H15A H -0.0738 0.3843 0.1572 0.156 Uiso 1 1 calc R U . . .
H15B H 0.1081 0.3547 0.1363 0.156 Uiso 1 1 calc R U . . .
H15C H 0.0195 0.4882 0.1066 0.156 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.185(6) . ?
O2 C1 1.353(6) . ?
O2 C4 1.453(5) . ?
O3 C3 1.420(4) . ?
O3 C6 1.429(4) . ?
O4 C5 1.404(4) . ?
O4 C14 1.414(5) . ?
O5 C15 1.409(4) . ?
O5 C7 1.424(3) . ?
C1 C2 1.488(7) . ?
C2 C3 1.504(5) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C4 1.502(5) . ?
C3 H3 0.98 . ?
C4 C5 1.526(4) . ?
C4 H4 0.98 . ?
C5 C6 1.524(4) . ?
C5 H5 0.98 . ?
C6 C7 1.514(4) . ?
C6 H6 0.98 . ?
C7 C8 1.508(4) . ?
C7 H7 0.98 . ?
C8 C9 1.385(4) . ?
C8 C13 1.387(5) . ?
C9 C10 1.380(6) . ?
C9 H9 0.93 . ?
C10 C11 1.352(7) . ?
C10 H10 0.93 . ?
C11 C12 1.391(8) . ?
C11 H11 0.93 . ?
C12 C13 1.396(6) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C4 110.8(3) . . ?
C3 O3 C6 110.2(2) . . ?
C5 O4 C14 114.2(4) . . ?
C15 O5 C7 113.3(3) . . ?
O1 C1 O2 121.6(5) . . ?
O1 C1 C2 129.7(5) . . ?
O2 C1 C2 108.7(4) . . ?
C1 C2 C3 104.5(3) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
O3 C3 C4 106.5(2) . . ?
O3 C3 C2 111.0(4) . . ?
C4 C3 C2 102.7(3) . . ?
O3 C3 H3 112.1 . . ?
C4 C3 H3 112.1 . . ?
C2 C3 H3 112.1 . . ?
O2 C4 C3 105.3(3) . . ?
O2 C4 C5 109.8(3) . . ?
C3 C4 C5 103.4(2) . . ?
O2 C4 H4 112.6 . . ?
C3 C4 H4 112.6 . . ?
C5 C4 H4 112.6 . . ?
O4 C5 C6 107.7(2) . . ?
O4 C5 C4 109.6(2) . . ?
C6 C5 C4 100.4(2) . . ?
O4 C5 H5 112.8 . . ?
C6 C5 H5 112.8 . . ?
C4 C5 H5 112.8 . . ?
O3 C6 C7 110.7(2) . . ?
O3 C6 C5 105.0(2) . . ?
C7 C6 C5 114.4(2) . . ?
O3 C6 H6 108.9 . . ?
C7 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
O5 C7 C8 111.9(2) . . ?
O5 C7 C6 106.0(2) . . ?
C8 C7 C6 111.8(2) . . ?
O5 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
C6 C7 H7 109.1 . . ?
C9 C8 C13 118.6(3) . . ?
C9 C8 C7 120.6(3) . . ?
C13 C8 C7 120.8(2) . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 120.1(4) . . ?
C10 C11 H11 120 . . ?
C12 C11 H11 120 . . ?
C11 C12 C13 119.5(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C8 C13 C12 120.3(3) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O2 C1 O1 -178.6(5) . . . . ?
C4 O2 C1 C2 2.0(5) . . . . ?
O1 C1 C2 C3 161.7(6) . . . . ?
O2 C1 C2 C3 -18.9(5) . . . . ?
C6 O3 C3 C4 2.2(4) . . . . ?
C6 O3 C3 C2 113.2(3) . . . . ?
C1 C2 C3 O3 -86.2(4) . . . . ?
C1 C2 C3 C4 27.3(5) . . . . ?
C1 O2 C4 C3 15.8(4) . . . . ?
C1 O2 C4 C5 126.6(3) . . . . ?
O3 C3 C4 O2 90.4(3) . . . . ?
C2 C3 C4 O2 -26.3(4) . . . . ?
O3 C3 C4 C5 -24.8(3) . . . . ?
C2 C3 C4 C5 -141.5(3) . . . . ?
C14 O4 C5 C6 166.8(4) . . . . ?
C14 O4 C5 C4 -84.9(5) . . . . ?
O2 C4 C5 O4 171.0(2) . . . . ?
C3 C4 C5 O4 -77.0(3) . . . . ?
O2 C4 C5 C6 -75.8(3) . . . . ?
C3 C4 C5 C6 36.1(3) . . . . ?
C3 O3 C6 C7 145.4(3) . . . . ?
C3 O3 C6 C5 21.4(3) . . . . ?
O4 C5 C6 O3 79.2(3) . . . . ?
C4 C5 C6 O3 -35.3(3) . . . . ?
O4 C5 C6 C7 -42.3(3) . . . . ?
C4 C5 C6 C7 -156.9(3) . . . . ?
C15 O5 C7 C8 67.6(3) . . . . ?
C15 O5 C7 C6 -170.4(3) . . . . ?
O3 C6 C7 O5 58.8(3) . . . . ?
C5 C6 C7 O5 177.1(2) . . . . ?
O3 C6 C7 C8 -179.1(2) . . . . ?
C5 C6 C7 C8 -60.8(3) . . . . ?
O5 C7 C8 C9 -121.4(3) . . . . ?
C6 C7 C8 C9 120.0(3) . . . . ?
O5 C7 C8 C13 57.9(3) . . . . ?
C6 C7 C8 C13 -60.7(3) . . . . ?
C13 C8 C9 C10 -0.8(5) . . . . ?
C7 C8 C9 C10 178.5(3) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C9 C10 C11 C12 0.9(6) . . . . ?
C10 C11 C12 C13 -1.8(6) . . . . ?
C9 C8 C13 C12 -0.2(4) . . . . ?
C7 C8 C13 C12 -179.5(3) . . . . ?
C11 C12 C13 C8 1.5(5) . . . . ?

#----------------------------------------------------------------------------#
#                   REFLECTION DATA AND REFINEMENT INSTRUCTIONS              #
#----------------------------------------------------------------------------#
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9
_database_code_depnum_ccdc_archive 'CCDC 1843448'
_audit_update_record             
;
2018-05-15 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
#exp_code: JF66-219_2061_s_abs_a

_audit_creation_date             2017-11-29T10:46:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
; 3,6-Anhydro-2-deoxy-5-O-methyl-7-C-phenyl-D-ido-hept-7-ulosono-1,4-lactone
;
_chemical_name_common            
; 3,6-Anhydro-2-deoxy-5-O-methyl-7-C-phenyl-D-ido-hept-7-ulosono-1,4-lactone
;
_chemical_formula_moiety         'C14 H14 O5'
_chemical_formula_sum            'C14 H14 O5'
_chemical_formula_weight         262.25
_chemical_melting_point          408
_chemical_compound_source        synthetic
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
_space_group_crystal_system      orthorhombic
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.6740(2)
_cell_length_b                   12.9175(7)
_cell_length_c                   21.3349(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1288.12(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2488
_cell_measurement_theta_min      3.148
_cell_measurement_theta_max      25.374

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.298
_exptl_crystal_size_min          0.177
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -3 5 0.0886
0 3 -5 0.0886
0 -3 -5 0.1521
5 -1 0 0.2457
-5 1 0 0.2457
0 0 1 0.0715
0 1 -5 0.1237
-1 1 -5 0.2098
0 5 3 0.151
3 3 5 0.2541
3 1 -5 0.2492
-3 -5 -1 0.2622
-1 0 -5 0.2153
0 -1 0 0.1407
0 5 -2 0.1341

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
 Analytical numeric absorption correction using a multifaceted crystal model 
 based on expressions derived by R.C. Clark & J.S. Reid (Clark, R. C. & 
 Reid, J. S. (1995). Acta Cryst. A51, 887-897) followed by empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK 
 scaling algorithm.
;
_exptl_transmission_factor_min   0.964
_exptl_transmission_factor_max   0.982
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.984

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.328
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.0272508
_diffrn_orient_matrix_ub_12      -0.0413423
_diffrn_orient_matrix_ub_13      -0.0210575
_diffrn_orient_matrix_ub_21      -0.046953
_diffrn_orient_matrix_ub_22      0.0359149
_diffrn_orient_matrix_ub_23      -0.0229333
_diffrn_orient_matrix_ub_31      0.1417381
_diffrn_orient_matrix_ub_32      0.0039714
_diffrn_orient_matrix_ub_33      -0.0116469
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_number            9417
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.154
_diffrn_reflns_theta_max         29.09
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.863
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.824
_reflns_Friedel_coverage         0.645
_reflns_number_total             2988
_reflns_number_gt                2246
_reflns_threshold_expression     'I > 2σ(I)'
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    
; SHELXT 2014/5 (Sheldrick, G.M. (2015). Acta Cryst. A71, 3--8,
 doi:10.1107/S2053273314026370)
;
_computing_structure_refinement  
; SHELXL-2017/1 (Sheldrick, G.M. (2015). Acta Cryst. C71, 3--8
        doi:10.1107/S2053229614024218)
;
_computing_molecular_graphics    
; Mercury CSD (Macrae, C.F.,  et al. (2008). J. Appl. Cryst. 41,
 466--470, doi:10.1107/S0021889807067908)
;
_computing_publication_material  
; SHELXLE (Hübschle, C.B., et al. (2011). J. Appl. Cryst., 44,
 1281--1284, doi:10.1107/S0021889811043202)'
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.1461P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2988
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
; Absolute structure parameter is meaningless because the compound is a weak 
 anomalous scatterer.

 Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 _refine_ls_abs_structure_Flack          0.3(5)
;
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.03

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4293(5) 0.93326(15) 0.36060(11) 0.0828(7) Uani 1 1 d . . . . .
O2 O 0.6585(4) 0.79585(13) 0.32432(8) 0.0633(5) Uani 1 1 d . . . . .
O3 O 0.7194(4) 0.67375(13) 0.44061(8) 0.0643(5) Uani 1 1 d . . . . .
O4 O 1.0211(4) 0.55105(13) 0.31823(7) 0.0552(5) Uani 1 1 d . . . . .
O5 O 1.0373(5) 0.50474(17) 0.46490(9) 0.0776(6) Uani 1 1 d . . . . .
C1 C 0.6108(6) 0.86885(19) 0.36883(13) 0.0586(7) Uani 1 1 d . . . . .
C2 C 0.8083(6) 0.85337(19) 0.42280(12) 0.0587(7) Uani 1 1 d . . . . .
H2A H 0.707448 0.859639 0.462351 0.07 Uiso 1 1 calc R U . . .
H2AB H 0.963906 0.90303 0.421875 0.07 Uiso 1 1 calc R U . . .
C3 C 0.9174(6) 0.74437(18) 0.41313(11) 0.0510(6) Uani 1 1 d . . . . .
H3 H 1.113887 0.73456 0.428008 0.061 Uiso 1 1 calc R U . . .
C4 C 0.8854(5) 0.72720(18) 0.34332(11) 0.0491(6) Uani 1 1 d . . . . .
H4 H 1.063713 0.741118 0.32068 0.059 Uiso 1 1 calc R U . . .
C5 C 0.7889(5) 0.61467(18) 0.33596(10) 0.0463(5) Uani 1 1 d . . . . .
H5 H 0.633074 0.609452 0.305401 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6830(6) 0.58538(17) 0.40202(11) 0.0502(6) Uani 1 1 d . . . . .
H6 H 0.478695 0.568805 0.399751 0.06 Uiso 1 1 calc R U . . .
C7 C 0.8427(5) 0.49186(19) 0.42839(11) 0.0513(6) Uani 1 1 d . . . . .
C8 C 0.7530(6) 0.38658(19) 0.40791(11) 0.0545(6) Uani 1 1 d . . . . .
C9 C 0.8751(9) 0.3020(2) 0.43571(16) 0.0866(10) Uani 1 1 d . . . . .
H9 H 1.014794 0.310882 0.466297 0.104 Uiso 1 1 calc R U . . .
C10 C 0.7909(13) 0.2027(3) 0.4183(2) 0.1136(15) Uani 1 1 d . . . . .
H10 H 0.870489 0.145581 0.438307 0.136 Uiso 1 1 calc R U . . .
C11 C 0.5947(11) 0.1888(3) 0.3727(2) 0.1105(16) Uani 1 1 d . . . . .
H11 H 0.544216 0.122146 0.360493 0.133 Uiso 1 1 calc R U . . .
C12 C 0.4707(10) 0.2718(3) 0.3447(2) 0.1103(14) Uani 1 1 d . . . . .
H12 H 0.33275 0.262106 0.313803 0.132 Uiso 1 1 calc R U . . .
C13 C 0.5507(8) 0.3709(2) 0.36223(16) 0.0837(9) Uani 1 1 d . . . . .
H13 H 0.466116 0.4276 0.342801 0.1 Uiso 1 1 calc R U . . .
C14 C 1.0436(9) 0.5364(4) 0.25289(14) 0.1012(13) Uani 1 1 d . . . . .
H14A H 1.213401 0.497455 0.243709 0.152 Uiso 1 1 calc R U . . .
H14B H 1.053638 0.60253 0.232448 0.152 Uiso 1 1 calc R U . . .
H14C H 0.87904 0.499321 0.238035 0.152 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.201(3) . ?
O2 C1 1.357(3) . ?
O2 C4 1.441(3) . ?
O3 C6 1.418(3) . ?
O3 C3 1.425(3) . ?
O4 C14 1.411(3) . ?
O4 C5 1.413(3) . ?
O5 C7 1.209(3) . ?
C1 C2 1.489(4) . ?
C2 C3 1.512(3) . ?
C2 H2A 0.97 . ?
C2 H2AB 0.97 . ?
C3 C4 1.513(3) . ?
C3 H3 0.98 . ?
C4 C5 1.530(3) . ?
C4 H4 0.98 . ?
C5 C6 1.541(3) . ?
C5 H5 0.98 . ?
C6 C7 1.527(3) . ?
C6 H6 0.98 . ?
C7 C8 1.489(3) . ?
C8 C9 1.368(4) . ?
C8 C13 1.373(4) . ?
C9 C10 1.392(5) . ?
C9 H9 0.93 . ?
C10 C11 1.349(6) . ?
C10 H10 0.93 . ?
C11 C12 1.358(6) . ?
C11 H11 0.93 . ?
C12 C13 1.386(4) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C4 110.6(2) . . ?
C6 O3 C3 110.75(18) . . ?
C14 O4 C5 113.6(2) . . ?
O1 C1 O2 119.7(3) . . ?
O1 C1 C2 130.1(3) . . ?
O2 C1 C2 110.2(2) . . ?
C1 C2 C3 103.2(2) . . ?
C1 C2 H2A 111.1 . . ?
C3 C2 H2A 111.1 . . ?
C1 C2 H2AB 111.1 . . ?
C3 C2 H2AB 111.1 . . ?
H2A C2 H2AB 109.1 . . ?
O3 C3 C2 108.7(2) . . ?
O3 C3 C4 104.30(19) . . ?
C2 C3 C4 103.7(2) . . ?
O3 C3 H3 113.1 . . ?
C2 C3 H3 113.1 . . ?
C4 C3 H3 113.1 . . ?
O2 C4 C3 105.04(19) . . ?
O2 C4 C5 109.8(2) . . ?
C3 C4 C5 105.63(19) . . ?
O2 C4 H4 112 . . ?
C3 C4 H4 112 . . ?
C5 C4 H4 112 . . ?
O4 C5 C4 110.72(19) . . ?
O4 C5 C6 110.41(18) . . ?
C4 C5 C6 103.53(18) . . ?
O4 C5 H5 110.7 . . ?
C4 C5 H5 110.7 . . ?
C6 C5 H5 110.7 . . ?
O3 C6 C7 111.4(2) . . ?
O3 C6 C5 107.15(18) . . ?
C7 C6 C5 111.97(19) . . ?
O3 C6 H6 108.8 . . ?
C7 C6 H6 108.8 . . ?
C5 C6 H6 108.8 . . ?
O5 C7 C8 121.8(2) . . ?
O5 C7 C6 119.7(2) . . ?
C8 C7 C6 118.5(2) . . ?
C9 C8 C13 118.5(3) . . ?
C9 C8 C7 119.0(3) . . ?
C13 C8 C7 122.5(3) . . ?
C8 C9 C10 120.1(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 120.5(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.7(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 121.0(3) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O2 C1 O1 179.6(2) . . . . ?
C4 O2 C1 C2 -0.3(3) . . . . ?
O1 C1 C2 C3 164.1(3) . . . . ?
O2 C1 C2 C3 -16.1(3) . . . . ?
C6 O3 C3 C2 139.7(2) . . . . ?
C6 O3 C3 C4 29.5(3) . . . . ?
C1 C2 C3 O3 -85.5(2) . . . . ?
C1 C2 C3 C4 25.0(3) . . . . ?
C1 O2 C4 C3 16.7(3) . . . . ?
C1 O2 C4 C5 129.9(2) . . . . ?
O3 C3 C4 O2 88.0(2) . . . . ?
C2 C3 C4 O2 -25.8(3) . . . . ?
O3 C3 C4 C5 -28.1(3) . . . . ?
C2 C3 C4 C5 -141.8(2) . . . . ?
C14 O4 C5 C4 -94.4(3) . . . . ?
C14 O4 C5 C6 151.6(3) . . . . ?
O2 C4 C5 O4 145.84(18) . . . . ?
C3 C4 C5 O4 -101.4(2) . . . . ?
O2 C4 C5 C6 -95.8(2) . . . . ?
C3 C4 C5 C6 17.0(3) . . . . ?
C3 O3 C6 C7 104.1(2) . . . . ?
C3 O3 C6 C5 -18.7(3) . . . . ?
O4 C5 C6 O3 118.6(2) . . . . ?
C4 C5 C6 O3 0.1(2) . . . . ?
O4 C5 C6 C7 -3.8(3) . . . . ?
C4 C5 C6 C7 -122.3(2) . . . . ?
O3 C6 C7 O5 -20.8(3) . . . . ?
C5 C6 C7 O5 99.2(3) . . . . ?
O3 C6 C7 C8 159.4(2) . . . . ?
C5 C6 C7 C8 -80.7(3) . . . . ?
O5 C7 C8 C9 6.5(4) . . . . ?
C6 C7 C8 C9 -173.7(3) . . . . ?
O5 C7 C8 C13 -173.8(3) . . . . ?
C6 C7 C8 C13 6.0(4) . . . . ?
C13 C8 C9 C10 -1.0(5) . . . . ?
C7 C8 C9 C10 178.7(3) . . . . ?
C8 C9 C10 C11 2.0(6) . . . . ?
C9 C10 C11 C12 -2.1(7) . . . . ?
C10 C11 C12 C13 1.2(7) . . . . ?
C9 C8 C13 C12 0.2(5) . . . . ?
C7 C8 C13 C12 -179.5(3) . . . . ?
C11 C12 C13 C8 -0.3(6) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_18
_database_code_depnum_ccdc_archive 'CCDC 1843445'
_audit_update_record             
;
2018-05-15 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
#exp_code: JF50A_1598

_audit_creation_date             2014-01-22T19:03:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
1,2-O-isopropylidene-3-O-methyl-5-C-phenil-β-L-ido-pentofuranose
_chemical_name_common            
1,2-O-isopropylidene-3-O-methyl-5-C-phenil-β-L-ido-pentofuranose
_chemical_formula_moiety         'C15 H20 O5'
_chemical_formula_structural     'C15 H20 O5'
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31
_chemical_melting_point          370
_chemical_compound_source        synthetic
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.8306(3)
_cell_length_b                   10.0761(3)
_cell_length_c                   17.1204(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1523.34(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    4914
_cell_measurement_theta_min      3.867
_cell_measurement_theta_max      28.317

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             600

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro 
 (Agilent Technologies,2013).
;
_exptl_absorpt_correction_T_min  0.89974
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.975

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo (Agilent Technologies)'
_diffrn_source_current           50
_diffrn_source_voltage           40
_diffrn_source_power             2
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.328
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_orient_matrix_ub_11      -0.0202388
_diffrn_orient_matrix_ub_12      -0.0670555
_diffrn_orient_matrix_ub_13      -0.0072283
_diffrn_orient_matrix_ub_21      -0.0032605
_diffrn_orient_matrix_ub_22      0.0134201
_diffrn_orient_matrix_ub_23      -0.0406493
_diffrn_orient_matrix_ub_31      0.0776914
_diffrn_orient_matrix_ub_32      -0.0168915
_diffrn_orient_matrix_ub_33      -0.0035662
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_number            13354
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         28.855
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.91
_reflns_number_total             3626
_reflns_number_gt                3218
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_structure_solution    
; SUPERFLIP (Palatinus L. and Chapuis G., 2007) and
  EDMA (Van Smaalen et al, 2003)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  
; SHELXLE (Hübschle et al., 2011) and WINGX (Farrugia, 2012)
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+0.1727P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.047(3)
_refine_ls_number_reflns         3626
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0849
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;

 The absolute structure parameter is essentially meaningless because 
 the compound is a weak anomalous scatterer.

 Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons et al., 2013).

_refine_ls_abs_structure_Flack          0.4(2)
;
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.024

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.95555(17) 0.28368(14) 0.83788(8) 0.0580(4) Uani 1 d . .
O2 O 0.8608(2) 0.10061(18) 0.77038(9) 0.0748(5) Uani 1 d . .
O3 O 0.68451(15) 0.08995(13) 0.86560(7) 0.0511(3) Uani 1 d . .
O4 O 0.92753(13) 0.24857(14) 1.00807(7) 0.0460(3) Uani 1 d . .
O5 O 0.9085(2) 0.56718(16) 0.84634(10) 0.0720(5) Uani 1 d . .
H5O H 0.985(4) 0.539(3) 0.8187(18) 0.098(10) Uiso 1 d . .
C1 C 0.9340(2) 0.1457(2) 0.83846(12) 0.0523(5) Uani 1 d . .
H1 H 1.0305 0.0993 0.8461 0.063 Uiso 1 calc . .
C2 C 0.8232(2) 0.11382(17) 0.90500(11) 0.0432(4) Uani 1 d . .
H2 H 0.8559 0.0387 0.9372 0.052 Uiso 1 calc . .
C3 C 0.81206(18) 0.24329(16) 0.95069(9) 0.0374(3) Uani 1 d . .
H3 H 0.7114 0.2552 0.9737 0.045 Uiso 1 calc . .
C4 C 0.8434(2) 0.34550(17) 0.88739(10) 0.0417(4) Uani 1 d . .
H4 H 0.7507 0.3588 0.8569 0.05 Uiso 1 calc . .
C5 C 0.9034(2) 0.48030(18) 0.91259(11) 0.0475(4) Uani 1 d . .
H5 H 1.0059 0.4697 0.9336 0.057 Uiso 1 calc . .
C6 C 0.8043(2) 0.54499(17) 0.97377(11) 0.0459(4) Uani 1 d . .
C7 C 0.8431(3) 0.5405(2) 1.05208(12) 0.0591(5) Uani 1 d . .
H7 H 0.9302 0.4957 1.0675 0.071 Uiso 1 calc . .
C8 C 0.7537(4) 0.6020(3) 1.10762(17) 0.0821(8) Uani 1 d . .
H8 H 0.7808 0.5973 1.16 0.098 Uiso 1 calc . .
C9 C 0.6269(4) 0.6689(3) 1.0866(2) 0.0943(11) Uani 1 d . .
H9 H 0.5686 0.7116 1.1242 0.113 Uiso 1 calc . .
C10 C 0.5854(3) 0.6732(3) 1.0100(2) 0.0938(10) Uani 1 d . .
H10 H 0.4974 0.7175 0.9956 0.113 Uiso 1 calc . .
C11 C 0.6737(3) 0.6116(2) 0.95273(16) 0.0666(6) Uani 1 d . .
H11 H 0.6447 0.6155 0.9006 0.08 Uiso 1 calc . .
C12 C 0.7185(3) 0.0419(2) 0.78942(12) 0.0541(5) Uani 1 d . .
C13 C 0.5995(3) 0.0928(3) 0.73394(16) 0.0890(9) Uani 1 d . .
H13A H 0.5939 0.1877 0.7376 0.134 Uiso 1 calc . .
H13B H 0.5031 0.0551 0.7473 0.134 Uiso 1 calc . .
H13C H 0.6257 0.068 0.6815 0.134 Uiso 1 calc . .
C14 C 0.7332(3) -0.1083(2) 0.78913(17) 0.0759(7) Uani 1 d . .
H14A H 0.6363 -0.1475 0.7998 0.114 Uiso 1 calc . .
H14B H 0.8043 -0.135 0.8285 0.114 Uiso 1 calc . .
H14C H 0.7683 -0.1372 0.7389 0.114 Uiso 1 calc . .
C15 C 0.8826(3) 0.1901(3) 1.07978(12) 0.0677(6) Uani 1 d . .
H15A H 0.792 0.2325 1.0982 0.101 Uiso 1 calc . .
H15B H 0.9618 0.2011 1.1177 0.101 Uiso 1 calc . .
H15C H 0.8636 0.0973 1.072 0.101 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.403(2) . ?
O1 C4 1.444(2) . ?
O2 C1 1.408(3) . ?
O2 C12 1.426(3) . ?
O3 C2 1.419(2) . ?
O3 C12 1.423(2) . ?
O4 C3 1.417(2) . ?
O4 C15 1.418(2) . ?
O5 C5 1.433(2) . ?
O5 H5O 0.87(3) . ?
C1 C2 1.536(3) . ?
C1 H1 0.98 . ?
C2 C3 1.524(2) . ?
C2 H2 0.98 . ?
C3 C4 1.520(2) . ?
C3 H3 0.98 . ?
C4 C5 1.520(2) . ?
C4 H4 0.98 . ?
C5 C6 1.512(3) . ?
C5 H5 0.98 . ?
C6 C11 1.382(3) . ?
C6 C7 1.385(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.93 . ?
C8 C9 1.355(5) . ?
C8 H8 0.93 . ?
C9 C10 1.362(5) . ?
C9 H9 0.93 . ?
C10 C11 1.398(4) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C13 1.506(3) . ?
C12 C14 1.519(3) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 109.29(13) . . ?
C1 O2 C12 110.43(15) . . ?
C2 O3 C12 108.13(15) . . ?
C3 O4 C15 112.54(14) . . ?
C5 O5 H5O 105(2) . . ?
O1 C1 O2 112.09(18) . . ?
O1 C1 C2 107.38(14) . . ?
O2 C1 C2 104.71(15) . . ?
O1 C1 H1 110.8 . . ?
O2 C1 H1 110.8 . . ?
C2 C1 H1 110.8 . . ?
O3 C2 C3 109.48(14) . . ?
O3 C2 C1 103.46(15) . . ?
C3 C2 C1 104.04(14) . . ?
O3 C2 H2 113 . . ?
C3 C2 H2 113 . . ?
C1 C2 H2 113 . . ?
O4 C3 C4 109.73(13) . . ?
O4 C3 C2 109.97(13) . . ?
C4 C3 C2 101.67(13) . . ?
O4 C3 H3 111.7 . . ?
C4 C3 H3 111.7 . . ?
C2 C3 H3 111.7 . . ?
O1 C4 C5 108.25(15) . . ?
O1 C4 C3 104.54(14) . . ?
C5 C4 C3 117.80(14) . . ?
O1 C4 H4 108.6 . . ?
C5 C4 H4 108.6 . . ?
C3 C4 H4 108.6 . . ?
O5 C5 C6 107.63(16) . . ?
O5 C5 C4 109.39(15) . . ?
C6 C5 C4 112.35(15) . . ?
O5 C5 H5 109.1 . . ?
C6 C5 H5 109.1 . . ?
C4 C5 H5 109.1 . . ?
C11 C6 C7 118.3(2) . . ?
C11 C6 C5 120.76(19) . . ?
C7 C6 C5 120.90(18) . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C6 C11 C10 119.9(3) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O3 C12 O2 104.75(15) . . ?
O3 C12 C13 108.35(18) . . ?
O2 C12 C13 109.2(2) . . ?
O3 C12 C14 111.08(19) . . ?
O2 C12 C14 109.7(2) . . ?
C13 C12 C14 113.3(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C1 O2 102.27(18) . . . . ?
C4 O1 C1 C2 -12.2(2) . . . . ?
C12 O2 C1 O1 -117.46(18) . . . . ?
C12 O2 C1 C2 -1.4(2) . . . . ?
C12 O3 C2 C3 138.50(15) . . . . ?
C12 O3 C2 C1 28.05(19) . . . . ?
O1 C1 C2 O3 103.21(17) . . . . ?
O2 C1 C2 O3 -16.10(19) . . . . ?
O1 C1 C2 C3 -11.2(2) . . . . ?
O2 C1 C2 C3 -130.52(16) . . . . ?
C15 O4 C3 C4 160.55(17) . . . . ?
C15 O4 C3 C2 -88.41(19) . . . . ?
O3 C2 C3 O4 162.14(13) . . . . ?
C1 C2 C3 O4 -87.80(16) . . . . ?
O3 C2 C3 C4 -81.64(16) . . . . ?
C1 C2 C3 C4 28.42(17) . . . . ?
C1 O1 C4 C5 157.30(16) . . . . ?
C1 O1 C4 C3 30.9(2) . . . . ?
O4 C3 C4 O1 80.21(16) . . . . ?
C2 C3 C4 O1 -36.19(16) . . . . ?
O4 C3 C4 C5 -40.0(2) . . . . ?
C2 C3 C4 C5 -156.36(16) . . . . ?
O1 C4 C5 O5 68.6(2) . . . . ?
C3 C4 C5 O5 -173.16(15) . . . . ?
O1 C4 C5 C6 -171.90(15) . . . . ?
C3 C4 C5 C6 -53.7(2) . . . . ?
O5 C5 C6 C11 39.5(2) . . . . ?
C4 C5 C6 C11 -81.0(2) . . . . ?
O5 C5 C6 C7 -139.60(19) . . . . ?
C4 C5 C6 C7 99.9(2) . . . . ?
C11 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C8 178.78(19) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C10 1.4(4) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C7 C6 C11 C10 0.5(3) . . . . ?
C5 C6 C11 C10 -178.6(2) . . . . ?
C9 C10 C11 C6 0.3(4) . . . . ?
C2 O3 C12 O2 -29.3(2) . . . . ?
C2 O3 C12 C13 -145.85(19) . . . . ?
C2 O3 C12 C14 89.0(2) . . . . ?
C1 O2 C12 O3 18.4(2) . . . . ?
C1 O2 C12 C13 134.3(2) . . . . ?
C1 O2 C12 C14 -100.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5O O2 0.87(3) 2.14(3) 2.874(2) 142(3) 3_756
#----------------------------------------------------------------------------#
#                        END OF CIF                                          #
#----------------------------------------------------------------------------#
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1843446'
_audit_update_record             
;
2018-05-15 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
#exp_code: JF83-258_1835_a

_audit_creation_date             2015-10-06T20:44:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
; 3,6-Anhydro-2-deoxy-7-O-methyl-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone
;
_chemical_name_common            
; 3,6-Anhydro-2-deoxy-7-O-methyl-7-C-phenyl-D-glycero-D-ido-heptono-1,4-lactone
;
_chemical_formula_moiety         'C14 H16 O5'
_chemical_formula_sum            'C14 H16 O5'
_chemical_formula_weight         264.27
_chemical_melting_point          396
_chemical_compound_source        synthetic
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
        They are only intended as comments.
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.6832(2)
_cell_length_b                   7.5202(3)
_cell_length_c                   11.6492(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.533(3)
_cell_angle_gamma                90
_cell_volume                     672.84(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6582
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      28.938
_cell_oxdiff_length_a            7.6819(3)
_cell_oxdiff_length_b            7.5195(3)
_cell_oxdiff_length_c            11.6520(5)
_cell_oxdiff_angle_alpha         89.998(3)
_cell_oxdiff_angle_beta          91.502(3)
_cell_oxdiff_angle_gamma         90.010(3)
_cell_oxdiff_volume              672.83(4)
_cell_oxdiff_measurement_reflns_used 6582

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             280

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.93743
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.973

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) (Oxford Diffraction)'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Sapphire3 (Oxford Diffraction)'
_diffrn_detector_area_resol_mean 16.328
_diffrn_orient_matrix_ub_11      0.0883379
_diffrn_orient_matrix_ub_12      -0.0077473
_diffrn_orient_matrix_ub_13      -0.015533
_diffrn_orient_matrix_ub_21      -0.0142959
_diffrn_orient_matrix_ub_22      -0.0902266
_diffrn_orient_matrix_ub_23      -0.0152998
_diffrn_orient_matrix_ub_31      -0.0228795
_diffrn_orient_matrix_ub_32      0.0263993
_diffrn_orient_matrix_ub_33      -0.0568577
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_number            14574
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.652
_diffrn_reflns_theta_max         28.946
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.911
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.872
_reflns_Friedel_coverage         0.797
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_number_total             3236
_reflns_number_gt                3035
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_shelx_SHELXL_version_number     2014/7
_computing_molecular_graphics    'Mercury CSD (Macrae et al., 2008)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.0972P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3236
_refine_ls_number_parameters     176
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.098
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
; Absolute structure parameter is meaningless because the compound is a 
 weak anomalous scatterer.

_refine_ls_abs_structure_details

 Flack x determined using 1250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

_refine_ls_abs_structure_Flack          -0.4(2)
;
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.64604(19) 0.7000(3) 0.99983(17) 0.0656(5) Uani 1 1 d . . . . .
O3 O 0.2617(2) 0.6669(2) 0.74251(13) 0.0515(4) Uani 1 1 d . . . . .
O4 O 0.35974(16) 0.7184(2) 1.00176(12) 0.0436(4) Uani 1 1 d . . . . .
O5 O -0.06760(18) 0.6936(3) 0.85931(16) 0.0609(5) Uani 1 1 d D . . . .
H5A H -0.138(3) 0.690(5) 0.912(2) 0.073 Uiso 1 1 d D U . . .
O7 O 0.0161(2) 0.2728(2) 0.80605(14) 0.0548(5) Uani 1 1 d . . . . .
C1 C 0.5128(2) 0.7472(3) 0.95239(18) 0.0426(5) Uani 1 1 d . . . . .
C2 C 0.4864(3) 0.8428(4) 0.8406(2) 0.0483(5) Uani 1 1 d . . . . .
H2A H 0.5565 0.7902 0.7815 0.058 Uiso 1 1 calc R U . . .
H2B H 0.5165 0.9675 0.8483 0.058 Uiso 1 1 calc R U . . .
C3 C 0.2939(3) 0.8201(3) 0.81250(19) 0.0429(4) Uani 1 1 d . . . . .
H3 H 0.2434 0.9277 0.7778 0.052 Uiso 1 1 calc R U . . .
C4 C 0.2150(2) 0.7792(3) 0.92888(18) 0.0404(5) Uani 1 1 d . . . . .
H4 H 0.1553 0.8821 0.9612 0.049 Uiso 1 1 calc R U . . .
C5 C 0.0923(2) 0.6246(3) 0.90419(16) 0.0388(4) Uani 1 1 d . . . . .
H5 H 0.0763 0.5494 0.9718 0.047 Uiso 1 1 calc R U . . .
C6 C 0.1892(2) 0.5288(3) 0.81021(17) 0.0354(4) Uani 1 1 d . . . . .
H6 H 0.2841 0.459 0.8455 0.042 Uiso 1 1 calc R U . . .
C7 C 0.0808(3) 0.4087(3) 0.73193(17) 0.0400(4) Uani 1 1 d . . . . .
H7 H -0.0176 0.4766 0.6993 0.048 Uiso 1 1 calc R U . . .
C8 C -0.1219(4) 0.1752(5) 0.7555(3) 0.0771(10) Uani 1 1 d . . . . .
H8A H -0.1602 0.0866 0.8085 0.116 Uiso 1 1 calc R U . . .
H8B H -0.083 0.1184 0.6869 0.116 Uiso 1 1 calc R U . . .
H8C H -0.2166 0.254 0.7364 0.116 Uiso 1 1 calc R U . . .
C9 C 0.1839(3) 0.3298(3) 0.63529(17) 0.0400(4) Uani 1 1 d . . . . .
C10 C 0.3382(3) 0.2394(3) 0.6576(2) 0.0527(5) Uani 1 1 d . . . . .
H10 H 0.3824 0.2324 0.7326 0.063 Uiso 1 1 calc R U . . .
C11 C 0.4272(4) 0.1596(4) 0.5701(3) 0.0687(7) Uani 1 1 d . . . . .
H11 H 0.5303 0.0989 0.5867 0.082 Uiso 1 1 calc R U . . .
C12 C 0.3646(4) 0.1693(4) 0.4587(3) 0.0701(8) Uani 1 1 d . . . . .
H12 H 0.4244 0.1144 0.4 0.084 Uiso 1 1 calc R U . . .
C13 C 0.2143(4) 0.2597(4) 0.4346(2) 0.0666(8) Uani 1 1 d . . . . .
H13 H 0.1725 0.2674 0.3591 0.08 Uiso 1 1 calc R U . . .
C14 C 0.1227(3) 0.3407(4) 0.5221(2) 0.0531(5) Uani 1 1 d . . . . .
H14 H 0.0204 0.4022 0.5047 0.064 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.204(3) . ?
O3 C6 1.427(2) . ?
O3 C3 1.429(3) . ?
O4 C1 1.340(2) . ?
O4 C4 1.454(2) . ?
O5 C5 1.421(2) . ?
O5 H5A 0.83(2) . ?
O7 C8 1.406(3) . ?
O7 C7 1.435(3) . ?
C1 C2 1.496(3) . ?
C2 C3 1.516(3) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C4 1.531(3) . ?
C3 H3 0.98 . ?
C4 C5 1.520(3) . ?
C4 H4 0.98 . ?
C5 C6 1.522(3) . ?
C5 H5 0.98 . ?
C6 C7 1.516(3) . ?
C6 H6 0.98 . ?
C7 C9 1.515(3) . ?
C7 H7 0.98 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 C10 1.385(3) . ?
C9 C14 1.391(3) . ?
C10 C11 1.379(4) . ?
C10 H10 0.93 . ?
C11 C12 1.374(5) . ?
C11 H11 0.93 . ?
C12 C13 1.362(5) . ?
C12 H12 0.93 . ?
C13 C14 1.394(4) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O3 C3 109.62(15) . . ?
C1 O4 C4 111.36(17) . . ?
C5 O5 H5A 107(2) . . ?
C8 O7 C7 112.88(19) . . ?
O1 C1 O4 120.0(2) . . ?
O1 C1 C2 129.4(2) . . ?
O4 C1 C2 110.58(18) . . ?
C1 C2 C3 104.03(17) . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 109 . . ?
O3 C3 C2 111.5(2) . . ?
O3 C3 C4 106.09(16) . . ?
C2 C3 C4 103.78(17) . . ?
O3 C3 H3 111.7 . . ?
C2 C3 H3 111.7 . . ?
C4 C3 H3 111.7 . . ?
O4 C4 C5 109.30(18) . . ?
O4 C4 C3 105.40(15) . . ?
C5 C4 C3 104.13(17) . . ?
O4 C4 H4 112.5 . . ?
C5 C4 H4 112.5 . . ?
C3 C4 H4 112.5 . . ?
O5 C5 C4 108.45(19) . . ?
O5 C5 C6 110.05(16) . . ?
C4 C5 C6 100.71(15) . . ?
O5 C5 H5 112.3 . . ?
C4 C5 H5 112.3 . . ?
C6 C5 H5 112.3 . . ?
O3 C6 C7 108.51(15) . . ?
O3 C6 C5 104.98(16) . . ?
C7 C6 C5 116.32(16) . . ?
O3 C6 H6 108.9 . . ?
C7 C6 H6 108.9 . . ?
C5 C6 H6 108.9 . . ?
O7 C7 C9 111.35(18) . . ?
O7 C7 C6 104.80(15) . . ?
C9 C7 C6 112.97(16) . . ?
O7 C7 H7 109.2 . . ?
C9 C7 H7 109.2 . . ?
C6 C7 H7 109.2 . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 118.2(2) . . ?
C10 C9 C7 121.01(18) . . ?
C14 C9 C7 120.7(2) . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 120.2(2) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O4 C1 O1 -177.9(2) . . . . ?
C4 O4 C1 C2 3.3(2) . . . . ?
O1 C1 C2 C3 165.2(3) . . . . ?
O4 C1 C2 C3 -16.1(3) . . . . ?
C6 O3 C3 C2 105.4(2) . . . . ?
C6 O3 C3 C4 -7.0(2) . . . . ?
C1 C2 C3 O3 -92.4(2) . . . . ?
C1 C2 C3 C4 21.4(2) . . . . ?
C1 O4 C4 C5 122.26(18) . . . . ?
C1 O4 C4 C3 10.9(2) . . . . ?
O3 C3 C4 O4 97.70(19) . . . . ?
C2 C3 C4 O4 -20.0(2) . . . . ?
O3 C3 C4 C5 -17.3(2) . . . . ?
C2 C3 C4 C5 -134.97(19) . . . . ?
O4 C4 C5 O5 165.10(15) . . . . ?
C3 C4 C5 O5 -82.66(18) . . . . ?
O4 C4 C5 C6 -79.37(18) . . . . ?
C3 C4 C5 C6 32.9(2) . . . . ?
C3 O3 C6 C7 153.63(17) . . . . ?
C3 O3 C6 C5 28.6(2) . . . . ?
O5 C5 C6 O3 76.5(2) . . . . ?
C4 C5 C6 O3 -37.8(2) . . . . ?
O5 C5 C6 C7 -43.4(2) . . . . ?
C4 C5 C6 C7 -157.71(17) . . . . ?
C8 O7 C7 C9 -72.8(3) . . . . ?
C8 O7 C7 C6 164.8(2) . . . . ?
O3 C6 C7 O7 178.92(17) . . . . ?
C5 C6 C7 O7 -63.1(2) . . . . ?
O3 C6 C7 C9 57.5(2) . . . . ?
C5 C6 C7 C9 175.53(18) . . . . ?
O7 C7 C9 C10 -64.7(3) . . . . ?
C6 C7 C9 C10 53.0(3) . . . . ?
O7 C7 C9 C14 113.0(2) . . . . ?
C6 C7 C9 C14 -129.4(2) . . . . ?
C14 C9 C10 C11 -1.1(4) . . . . ?
C7 C9 C10 C11 176.6(2) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C10 C9 C14 C13 1.0(4) . . . . ?
C7 C9 C14 C13 -176.7(2) . . . . ?
C12 C13 C14 C9 -0.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O1 0.83(2) 1.98(2) 2.778(2) 163(3) 1_455

#----------------------------------------------------------------------------#
#                   REFLECTION DATA AND REFINEMENT INSTRUCTIONS              #
#----------------------------------------------------------------------------#
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_17
_database_code_depnum_ccdc_archive 'CCDC 1843447'
_audit_update_record             
;
2018-05-15 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
#exp_code: JF50B_1599

_audit_creation_date             2014-01-23T09:52:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
1,2-O-isopropylidene-3-O-methyl-5-C-phenil-α-D-gluco-pentofuranose
_chemical_name_common            
1,2-O-isopropylidene-3-O-methyl-5-C-phenil-α-D-gluco-pentofuranose
_chemical_formula_moiety         'C15 H20 O5'
_chemical_formula_structural     'C15 H20 O5'
_chemical_formula_sum            'C15 H20 O5'
_chemical_formula_weight         280.31
_chemical_melting_point          344
_chemical_compound_source        synthetic
_chemical_absolute_configuration rm

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   11.0585(4)
_cell_length_b                   11.4256(3)
_cell_length_c                   11.8876(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1502.00(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5669
_cell_measurement_theta_min      4.085
_cell_measurement_theta_max      28.772

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.6
_exptl_crystal_density_diffrn    1.24
_exptl_crystal_F_000             600

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro 
 (Agilent Technologies,2013).
;
_exptl_absorpt_correction_T_min  0.93326
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.93
_shelx_estimated_absorpt_T_max   0.947

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo (Agilent Technologies)'
_diffrn_source_current           50
_diffrn_source_voltage           40
_diffrn_source_power             2
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.328
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_orient_matrix_ub_11      0.0597266
_diffrn_orient_matrix_ub_12      -0.0184011
_diffrn_orient_matrix_ub_13      0.0126162
_diffrn_orient_matrix_ub_21      -0.0229088
_diffrn_orient_matrix_ub_22      -0.0531633
_diffrn_orient_matrix_ub_23      0.0222122
_diffrn_orient_matrix_ub_31      0.0045503
_diffrn_orient_matrix_ub_32      -0.0262493
_diffrn_orient_matrix_ub_33      -0.0539321
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_number            12380
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.428
_diffrn_reflns_theta_max         29.094
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.88
_reflns_number_total             3542
_reflns_number_gt                3338
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_structure_solution    
; SUPERFLIP (Palatinus L. and Chapuis G., 2007) and
  EDMA (Van Smaalen et al, 2003)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  
; SHELXLE (Hübschle et al., 2011) and WINGX (Farrugia, 2012)
;
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.1550P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3542
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0977
_refine_ls_wR_factor_gt          0.096
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1296 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons et al., 2013).
 Absolute structure parameter is essentially meaningless because 
 the compound is a weak anomalous scatterer
;
_refine_ls_abs_structure_Flack   -0.04(23)
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.21
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51540(14) 0.27474(11) 0.73064(11) 0.0412(3) Uani 1 d . .
O2 O 0.38081(13) 0.22829(11) 0.87343(13) 0.0445(4) Uani 1 d . .
O3 O 0.36012(13) 0.42345(12) 0.89750(13) 0.0429(3) Uani 1 d . .
O4 O 0.65763(13) 0.47830(12) 0.77978(13) 0.0432(3) Uani 1 d . .
O5 O 0.53689(16) 0.51556(13) 0.53151(14) 0.0511(4) Uani 1 d . .
H5O H 0.575(2) 0.564(3) 0.566(2) 0.052(7) Uiso 1 d . .
C1 C 0.49420(17) 0.27621(15) 0.84673(15) 0.0350(4) Uani 1 d . .
H1 H 0.559 0.2356 0.8873 0.042 Uiso 1 calc . .
C2 C 0.48637(18) 0.40463(15) 0.88288(15) 0.0360(4) Uani 1 d . .
H2 H 0.5335 0.4217 0.9507 0.043 Uiso 1 calc . .
C3 C 0.53005(17) 0.47156(15) 0.78022(16) 0.0332(4) Uani 1 d . .
H3 H 0.4921 0.5488 0.7739 0.04 Uiso 1 calc . .
C4 C 0.49092(17) 0.38897(14) 0.68613(15) 0.0325(4) Uani 1 d . .
H4 H 0.4038 0.3973 0.6735 0.039 Uiso 1 calc . .
C5 C 0.55723(17) 0.40128(16) 0.57435(16) 0.0351(4) Uani 1 d . .
H5 H 0.6441 0.3893 0.5861 0.042 Uiso 1 calc . .
C6 C 0.51106(18) 0.31411(16) 0.48872(14) 0.0361(4) Uani 1 d . .
C7 C 0.5702(2) 0.20916(19) 0.47193(19) 0.0484(5) Uani 1 d . .
H7 H 0.6401 0.1924 0.5124 0.058 Uiso 1 calc . .
C8 C 0.5261(3) 0.1285(2) 0.3950(2) 0.0629(7) Uani 1 d . .
H8 H 0.5664 0.0579 0.3844 0.075 Uiso 1 calc . .
C9 C 0.4244(3) 0.1518(3) 0.3350(2) 0.0690(8) Uani 1 d . .
H9 H 0.3957 0.0977 0.2829 0.083 Uiso 1 calc . .
C10 C 0.3645(3) 0.2544(3) 0.3512(2) 0.0665(8) Uani 1 d . .
H10 H 0.2944 0.27 0.3107 0.08 Uiso 1 calc . .
C11 C 0.4074(2) 0.3360(2) 0.4277(2) 0.0520(5) Uani 1 d . .
H11 H 0.366 0.406 0.438 0.062 Uiso 1 calc . .
C12 C 0.30694(18) 0.31453(18) 0.92803(17) 0.0403(4) Uani 1 d . .
C13 C 0.3121(2) 0.2964(3) 1.0539(2) 0.0591(6) Uani 1 d . .
H13A H 0.2817 0.22 1.072 0.089 Uiso 1 calc . .
H13B H 0.2635 0.3547 1.0905 0.089 Uiso 1 calc . .
H13C H 0.3943 0.3031 1.0791 0.089 Uiso 1 calc . .
C14 C 0.1814(2) 0.3075(3) 0.8803(2) 0.0588(6) Uani 1 d . .
H14A H 0.1484 0.2313 0.8946 0.088 Uiso 1 calc . .
H14B H 0.1843 0.3211 0.8006 0.088 Uiso 1 calc . .
H14C H 0.1313 0.3658 0.9151 0.088 Uiso 1 calc . .
C15 C 0.7059(2) 0.5649(2) 0.8532(2) 0.0522(5) Uani 1 d . .
H15A H 0.7923 0.567 0.8457 0.078 Uiso 1 calc . .
H15B H 0.685 0.5461 0.9295 0.078 Uiso 1 calc . .
H15C H 0.6729 0.64 0.834 0.078 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.400(2) . ?
O1 C4 1.434(2) . ?
O2 C1 1.405(2) . ?
O2 C12 1.435(2) . ?
O3 C2 1.423(2) . ?
O3 C12 1.423(2) . ?
O4 C3 1.413(2) . ?
O4 C15 1.423(3) . ?
O5 C5 1.419(2) . ?
O5 H5O 0.81(3) . ?
C1 C2 1.531(2) . ?
C1 H1 0.98 . ?
C2 C3 1.519(3) . ?
C2 H2 0.98 . ?
C3 C4 1.526(2) . ?
C3 H3 0.98 . ?
C4 C5 1.524(3) . ?
C4 H4 0.98 . ?
C5 C6 1.513(3) . ?
C5 H5 0.98 . ?
C6 C11 1.379(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.93 . ?
C8 C9 1.358(4) . ?
C8 H8 0.93 . ?
C9 C10 1.360(4) . ?
C9 H9 0.93 . ?
C10 C11 1.386(4) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C12 C14 1.502(3) . ?
C12 C13 1.511(3) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 108.74(13) . . ?
C1 O2 C12 110.05(14) . . ?
C2 O3 C12 107.72(14) . . ?
C3 O4 C15 114.20(16) . . ?
C5 O5 H5O 111(2) . . ?
O1 C1 O2 111.57(15) . . ?
O1 C1 C2 107.31(14) . . ?
O2 C1 C2 105.04(15) . . ?
O1 C1 H1 110.9 . . ?
O2 C1 H1 110.9 . . ?
C2 C1 H1 110.9 . . ?
O3 C2 C3 109.51(15) . . ?
O3 C2 C1 103.56(14) . . ?
C3 C2 C1 103.82(14) . . ?
O3 C2 H2 113.1 . . ?
C3 C2 H2 113.1 . . ?
C1 C2 H2 113.1 . . ?
O4 C3 C2 110.36(15) . . ?
O4 C3 C4 108.31(15) . . ?
C2 C3 C4 100.80(14) . . ?
O4 C3 H3 112.3 . . ?
C2 C3 H3 112.3 . . ?
C4 C3 H3 112.3 . . ?
O1 C4 C5 108.35(14) . . ?
O1 C4 C3 103.81(14) . . ?
C5 C4 C3 116.45(15) . . ?
O1 C4 H4 109.3 . . ?
C5 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
O5 C5 C6 108.10(16) . . ?
O5 C5 C4 108.75(15) . . ?
C6 C5 C4 111.31(14) . . ?
O5 C5 H5 109.6 . . ?
C6 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
C11 C6 C7 118.38(19) . . ?
C11 C6 C5 121.00(19) . . ?
C7 C6 C5 120.60(18) . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C10 120.5(2) . . ?
C6 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
O3 C12 O2 104.47(14) . . ?
O3 C12 C14 109.39(18) . . ?
O2 C12 C14 108.59(18) . . ?
O3 C12 C13 110.88(18) . . ?
O2 C12 C13 109.42(19) . . ?
C14 C12 C13 113.7(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C1 O2 99.91(16) . . . . ?
C4 O1 C1 C2 -14.6(2) . . . . ?
C12 O2 C1 O1 -118.99(16) . . . . ?
C12 O2 C1 C2 -3.04(19) . . . . ?
C12 O3 C2 C3 138.71(15) . . . . ?
C12 O3 C2 C1 28.45(18) . . . . ?
O1 C1 C2 O3 103.50(17) . . . . ?
O2 C1 C2 O3 -15.35(18) . . . . ?
O1 C1 C2 C3 -10.9(2) . . . . ?
O2 C1 C2 C3 -129.75(15) . . . . ?
C15 O4 C3 C2 -78.8(2) . . . . ?
C15 O4 C3 C4 171.73(17) . . . . ?
O3 C2 C3 O4 165.49(14) . . . . ?
C1 C2 C3 O4 -84.43(17) . . . . ?
O3 C2 C3 C4 -80.19(16) . . . . ?
C1 C2 C3 C4 29.90(17) . . . . ?
C1 O1 C4 C5 158.75(15) . . . . ?
C1 O1 C4 C3 34.36(19) . . . . ?
O4 C3 C4 O1 76.67(17) . . . . ?
C2 C3 C4 O1 -39.19(17) . . . . ?
O4 C3 C4 C5 -42.3(2) . . . . ?
C2 C3 C4 C5 -158.17(15) . . . . ?
O1 C4 C5 O5 -178.03(15) . . . . ?
C3 C4 C5 O5 -61.5(2) . . . . ?
O1 C4 C5 C6 63.0(2) . . . . ?
C3 C4 C5 C6 179.48(16) . . . . ?
O5 C5 C6 C11 -37.4(2) . . . . ?
C4 C5 C6 C11 81.9(2) . . . . ?
O5 C5 C6 C7 144.26(18) . . . . ?
C4 C5 C6 C7 -96.4(2) . . . . ?
C11 C6 C7 C8 0.3(3) . . . . ?
C5 C6 C7 C8 178.6(2) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C7 C6 C11 C10 -0.3(3) . . . . ?
C5 C6 C11 C10 -178.6(2) . . . . ?
C9 C10 C11 C6 -0.2(4) . . . . ?
C2 O3 C12 O2 -30.66(19) . . . . ?
C2 O3 C12 C14 -146.75(18) . . . . ?
C2 O3 C12 C13 87.1(2) . . . . ?
C1 O2 C12 O3 20.4(2) . . . . ?
C1 O2 C12 C14 137.00(18) . . . . ?
C1 O2 C12 C13 -98.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5O O2 0.81(3) 2.07(3) 2.831(2) 156(3) 4_656
