# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_acireduct_powder
_database_code_depnum_ccdc_archive 'CCDC 1452494'
_audit_update_record             
;
2016-02-16 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_acireduct_powder    
;
PROBLEM: Short Inter D...A Contact  O1     ..  O5      ..       2.70 Ang.
RESPONSE: There is a H-bond present here though the missing hydrogen atom could not have been located
;

# Added during the CSD deposition process: Tuesday 16th of February 2016 12:06:21 PM
# end Validation Reply Form

_publcif_datablock.id            {526af255-4200-42ec-9dd2-cfddfe0438de}

#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
1,1'-[4-hydroxy-2-(hydroxymethyl)-1,3-dioxolane-2,4-diyl]di(butan-1-one)
;
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H20 O6'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H20 O6'
_chemical_formula_weight         260.3
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2

_cell_length_a                   5.46953(4)
_cell_length_b                   25.01189(17)
_cell_length_c                   10.72878(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.0587(7)
_cell_angle_gamma                90
_cell_volume                     1350.467(19)


_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_special_details            ?

_exptl_crystal_density_diffrn    1.2802
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             560

_pd_spec_size_axial              ?
_pd_spec_size_equat              ?
_pd_spec_size_thick              ?
_pd_spec_mounting                ?
_pd_spec_mount_mode              ?
_pd_spec_shape                   ?
_pd_char_particle_morphology     ?
_pd_char_colour                  colourless
_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             ?

_exptl_absorpt_coefficient_mu    0.04
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?
_pd_instr_location               ?
_pd_calibration_special_details  ?

_diffrn_ambient_temperature      293
_diffrn_source                   ?
_diffrn_source_target            ?
_diffrn_source_type              ?
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40087
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'synchrotron - ID31 beamline'
_diffrn_detector                 ?
_diffrn_detector_type            ?

_pd_meas_scan_method             ?
_pd_meas_special_details         ?
_pd_meas_number_of_points        12250
_pd_meas_2theta_range_min        0.502
_pd_meas_2theta_range_max        25.000
_pd_meas_2theta_range_inc        0.002

_diffrn_radiation_probe          x-ray

#=======================================================================

# 8. REFINEMENT DATA

_pd_proc_ls_special_details      ?
_pd_proc_ls_profile_function     Pseudo-Voigt
_pd_proc_ls_background_function  '15 Legendre polynoms'
_pd_proc_ls_pref_orient_corr     none
_pd_proc_ls_prof_R_factor        0.0401
_pd_proc_ls_prof_wR_factor       0.0510
_pd_proc_ls_prof_wR_expected     0.0259

_refine_special_details          
;
Restrained Rietveld refinement based on synchrotron data with additional
constraints:
- planarity at the carbonyl C-atoms is fixed.
- Uiso are restricted to a single value
;

_refine_ls_R_factor_gt           0.1033
_refine_ls_wR_factor_gt          0.0834
_refine_ls_R_factor_all          0.1309
_refine_ls_wR_factor_all         0.0873
_refine_ls_goodness_of_fit_all   1.97
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_parameters     79
_refine_ls_number_restraints     13
_refine_ls_number_constraints    88
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0412
_refine_ls_shift/su_mean         0.0025
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?

_pd_proc_2theta_range_min        0.502
_pd_proc_2theta_range_max        25
_pd_proc_2theta_range_inc        0.002
_pd_proc_wavelength              ?

_pd_block_diffractogram_id       ?

_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C -0.0001 0.0005 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0016 0.0017 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_restr_distance_atom_site_label_1
_restr_distance_site_symmetry_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
C6 . O1 . 1.42 0.01
C12 . O4 . 1.42 0.01
O3 . C4 . 1.23 0.02
O6 . C10 . 1.23 0.02


loop_
_restr_angle_atom_site_label_1
_restr_angle_site_symmetry_1
_restr_angle_atom_site_label_2
_restr_angle_site_symmetry_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_torsion_atom_site_label_1
_restr_torsion_site_symmetry_1
_restr_torsion_atom_site_label_2
_restr_torsion_site_symmetry_2
_restr_torsion_atom_site_label_3
_restr_torsion_site_symmetry_3
_restr_torsion_atom_site_label_4
_restr_torsion_site_symmetry_4
_restr_torsion_angle_target
_restr_torsion_weight_param
? ? ? ? ? ? ? ? ? ?

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_site_symmetry_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
C1 . C2 . 1 0.005
C2 . C3 . 1 0.005
C3 . C4 . 1 0.005
C4 . C5 . 1 0.005
C5 . C6 . 1 0.005
C7 . C8 . 1 0.005
C8 . C9 . 1 0.005
C9 . C10 . 1 0.005
C10 . C11 . 1 0.005
C11 . C12 . 1 0.005


loop_
_restr_equal_angle_atom_site_label_1
_restr_equal_angle_site_symmetry_1
_restr_equal_angle_atom_site_label_2
_restr_equal_angle_site_symmetry_2
_restr_equal_angle_atom_site_label_3
_restr_equal_angle_site_symmetry_3
_restr_equal_angle_class_class_id
_restr_equal_angle_class_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_equal_torsion_atom_site_label_1
_restr_equal_torsion_site_symmetry_1
_restr_equal_torsion_atom_site_label_2
_restr_equal_torsion_site_symmetry_2
_restr_equal_torsion_atom_site_label_3
_restr_equal_torsion_site_symmetry_3
_restr_equal_torsion_atom_site_label_4
_restr_equal_torsion_site_symmetry_4
_restr_equal_torsion_class_class_id
_restr_equal_torsion_class_target_weight_param
? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5398(19) -0.0842(4) 1.0433(10) Uiso 0.0382(19) 4 1 d . . .
C2 C 0.3296(16) -0.1173(3) 1.0667(10) Uiso 0.0382(19) 4 1 d . . .
C3 C 0.3104(19) -0.1747(4) 1.0176(9) Uiso 0.0382(19) 4 1 d . . .
C4 C 0.1057(16) -0.2138(4) 1.0257(9) Uiso 0.0382(19) 4 1 d . . .
C5 C 0.027(2) -0.2663(5) 0.9498(12) Uiso 0.0382(19) 4 1 d . . .
C6 C -0.220(2) -0.2585(4) 0.8209(8) Uiso 0.0382(19) 4 1 d . . .
O1 O -0.2043(17) -0.2185(3) 0.7421(8) Uiso 0.0348(14) 4 1 d . . .
O2 O 0.0434(19) -0.3026(4) 1.0514(10) Uiso 0.0348(14) 4 1 d . . .
O3 O 0.0096(17) -0.1987(3) 1.1003(9) Uiso 0.0348(14) 4 1 d . . .
C7 C -0.2069(18) -0.4920(4) 1.2474(7) Uiso 0.0382(19) 4 1 d . . .
C8 C -0.2217(17) -0.4626(4) 1.1192(9) Uiso 0.0382(19) 4 1 d . . .
C9 C 0.0061(17) -0.4232(4) 1.1546(11) Uiso 0.0382(19) 4 1 d . . .
C10 C -0.0058(19) -0.3971(4) 1.0249(11) Uiso 0.0382(19) 4 1 d . . .
C11 C 0.184(3) -0.3502(5) 1.0502(12) Uiso 0.0382(19) 4 1 d . . .
C12 C 0.2783(19) -0.3357(4) 0.9400(10) Uiso 0.0382(19) 4 1 d . . .
O4 O 0.2598(17) -0.2789(3) 0.9337(8) Uiso 0.0348(14) 4 1 d . . .
O5 O 0.4037(15) -0.3548(3) 1.1770(8) Uiso 0.0348(14) 4 1 d . . .
O6 O -0.1483(13) -0.4108(3) 0.9110(7) Uiso 0.0348(14) 4 1 d . . .
H3 H 0.670975 -0.072946 1.128909 Uiso 0.0458 4 1 d . . .
H1 H 0.623287 -0.105399 0.996399 Uiso 0.0458 4 1 d . . .
H2 H 0.458439 -0.053431 0.989817 Uiso 0.0458 4 1 d . . .
H4 H 0.159829 -0.100245 1.024183 Uiso 0.0458 4 1 d . . .
H5 H 0.362081 -0.117053 1.161392 Uiso 0.0458 4 1 d . . .
H6 H 0.309178 -0.175207 0.927916 Uiso 0.0458 4 1 d . . .
H7 H 0.483194 -0.190916 1.054558 Uiso 0.0458 4 1 d . . .
H8 H -0.259961 -0.291163 0.769829 Uiso 0.0458 4 1 d . . .
H9 H -0.37148 -0.253193 0.843558 Uiso 0.0458 4 1 d . . .
H12 H -0.036413 -0.485809 1.318863 Uiso 0.0458 4 1 d . . .
H13 H -0.343911 -0.478858 1.274301 Uiso 0.0458 4 1 d . . .
H11 H -0.231283 -0.529588 1.229169 Uiso 0.0458 4 1 d . . .
H15 H -0.21069 -0.488014 1.054603 Uiso 0.0458 4 1 d . . .
H14 H -0.387328 -0.443677 1.08046 Uiso 0.0458 4 1 d . . .
H17 H 0.17165 -0.441959 1.196412 Uiso 0.0458 4 1 d . . .
H16 H -0.011476 -0.396408 1.214471 Uiso 0.0458 4 1 d . . .
H19 H 0.460597 -0.346196 0.96689 Uiso 0.0458 4 1 d . . .
H18 H 0.159461 -0.350594 0.855538 Uiso 0.0458 4 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_type_symbol
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . . 1.515(15) ?
C1 H3 . . 0.96 ?
C1 H1 . . 0.96 ?
C1 H2 . . 0.96 ?
C2 C3 . . 1.517(13) ?
C2 H4 . . 0.96 ?
C2 H5 . . 0.96 ?
C3 C4 . . 1.515(15) ?
C3 H6 . . 0.96 ?
C3 H7 . . 0.96 ?
C4 C5 . . 1.515(16) ?
C4 O3 . . 1.178(15) ?
C5 C6 . . 1.519(12) ?
C5 O2 . . 1.395(17) ?
C5 O4 . . 1.389(17) ?
C6 O1 . . 1.334(13) ?
C6 H8 . . 0.96 ?
C6 H9 . . 0.96 ?
O2 C11 . . 1.420(17) ?
C7 C8 . . 1.533(13) ?
C7 H12 . . 0.96 ?
C7 H13 . . 0.96 ?
C7 H11 . . 0.96 ?
C8 C9 . . 1.514(13) ?
C8 H15 . . 0.96 ?
C8 H14 . . 0.96 ?
C9 C10 . . 1.515(16) ?
C9 H17 . . 0.96 ?
C9 H16 . . 0.96 ?
C10 C11 . . 1.517(16) ?
C10 O6 . . 1.213(11) ?
C11 C12 . . 1.51(2) ?
C11 O5 . . 1.424(12) ?
C12 O4 . . 1.423(13) ?
C12 H19 . . 0.96 ?
C12 H18 . . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H3 . . . 109.47 ?
C2 C1 H1 . . . 109.47 ?
C2 C1 H2 . . . 109.47 ?
H3 C1 H1 . . . 109.47 ?
H3 C1 H2 . . . 109.47 ?
H1 C1 H2 . . . 109.47 ?
C1 C2 C3 . . . 114.4(9) ?
C1 C2 H4 . . . 109.47 ?
C1 C2 H5 . . . 109.47 ?
C3 C2 H4 . . . 109.47 ?
C3 C2 H5 . . . 109.47 ?
H4 C2 H5 . . . 102.97 ?
C2 C3 C4 . . . 122.9(10) ?
C2 C3 H6 . . . 109.47 ?
C2 C3 H7 . . . 109.47 ?
C4 C3 H6 . . . 109.47 ?
C4 C3 H7 . . . 109.47 ?
H6 C3 H7 . . . 91.87 ?
C3 C4 C5 . . . 126.2(10) ?
C3 C4 O3 . . . 111.6(9) ?
C5 C4 O3 . . . 122.2(10) ?
C4 C5 C6 . . . 110.1(9) ?
C4 C5 O2 . . . 103.1(9) ?
C4 C5 O4 . . . 100.4(9) ?
C6 C5 O2 . . . 123.9(10) ?
C6 C5 O4 . . . 116.6(10) ?
O2 C5 O4 . . . 99.5(9) ?
C5 C6 O1 . . . 114.7(9) ?
C5 C6 H8 . . . 109.47 ?
C5 C6 H9 . . . 109.47 ?
O1 C6 H8 . . . 109.47 ?
O1 C6 H9 . . . 109.47 ?
H8 C6 H9 . . . 101.22 ?
C5 O2 C11 . . . 114.2(12) ?
C8 C7 H12 . . . 109.47 ?
C8 C7 H13 . . . 109.47 ?
C8 C7 H11 . . . 109.47 ?
H12 C7 H13 . . . 109.47 ?
H12 C7 H11 . . . 109.47 ?
H13 C7 H11 . . . 109.47 ?
C7 C8 C9 . . . 109.7(7) ?
C7 C8 H15 . . . 109.47 ?
C7 C8 H14 . . . 109.47 ?
C9 C8 H15 . . . 109.47 ?
C9 C8 H14 . . . 109.47 ?
H15 C8 H14 . . . 111.25 ?
C8 C9 C10 . . . 108.3(7) ?
C8 C9 H17 . . . 109.47 ?
C8 C9 H16 . . . 109.47 ?
C10 C9 H17 . . . 109.47 ?
C10 C9 H16 . . . 109.47 ?
H17 C9 H16 . . . 112.08 ?
C9 C10 C11 . . . 112.9(8) ?
C9 C10 O6 . . . 125.6(9) ?
C11 C10 O6 . . . 121.5(11) ?
O2 C11 C10 . . . 108.4(11) ?
O2 C11 C12 . . . 99.0(10) ?
O2 C11 O5 . . . 108.4(9) ?
C10 C11 C12 . . . 117.8(10) ?
C10 C11 O5 . . . 111.8(10) ?
C12 C11 O5 . . . 110.3(10) ?
C11 C12 O4 . . . 103.8(10) ?
C11 C12 H19 . . . 109.47 ?
C11 C12 H18 . . . 109.47 ?
O4 C12 H19 . . . 109.47 ?
O4 C12 H18 . . . 109.47 ?
H19 C12 H18 . . . 115.32 ?
C5 O4 C12 . . . 105.8(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C12 H18 O6 . . . 0.96 2.50 2.916(13) 106.20 ?
_exptl_crystal_colour            colourless
####################################################################### 
# 
# 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_acired_comput
_database_code_depnum_ccdc_archive 'CCDC 1452495'
_audit_update_record             
;
2016-02-16 deposited with the CCDC.
2016-09-07 downloaded from the CCDC.
;

#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
1,1'-[4-hydroxy-2-(hydroxymethyl)-1,3-dioxolane-2,4-diyl]di(butan-1-one)
;
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H20 O6'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C12 H20 O6'
_chemical_formula_weight         260.3
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

#=======================================================================

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2

_cell_length_a                   5.4695
_cell_length_b                   25.0119
_cell_length_c                   10.7288
_cell_angle_alpha                90
_cell_angle_beta                 113.059
_cell_angle_gamma                90
_cell_volume                     1350.459


_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_special_details            ?

_exptl_crystal_density_diffrn    1.2802
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             560

_pd_spec_size_axial              ?
_pd_spec_size_equat              ?
_pd_spec_size_thick              ?
_pd_spec_mounting                ?
_pd_spec_mount_mode              ?
_pd_spec_shape                   ?
_pd_char_particle_morphology     ?
_pd_char_colour                  colourless
_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             ?

_exptl_absorpt_coefficient_mu    0.04
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?
_pd_instr_location               ?
_pd_calibration_special_details  ?

_diffrn_ambient_temperature      293
_diffrn_source                   ?
_diffrn_source_target            ?
_diffrn_source_type              ?
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40087
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'synchrotron - ID31 beamline'
_diffrn_detector                 ?
_diffrn_detector_type            ?

_pd_meas_scan_method             ?
_pd_meas_special_details         ?
_pd_meas_number_of_points        12250
_pd_meas_2theta_range_min        0.502
_pd_meas_2theta_range_max        25.000
_pd_meas_2theta_range_inc        0.002

_diffrn_radiation_probe          x-ray

#=======================================================================

# 8. REFINEMENT DATA

_pd_proc_ls_special_details      ?
_pd_proc_ls_profile_function     Pseudo-Voigt
_pd_proc_ls_background_function  
'Manual background combined with 15 Legendre polynoms'
_pd_proc_ls_pref_orient_corr     none
_pd_proc_ls_prof_R_factor        0.0457
_pd_proc_ls_prof_wR_factor       0.0671
_pd_proc_ls_prof_wR_expected     0.0260

_refine_special_details          
;
Atomic position refined by periodic DFT calculations
Uiso refined based on synchrotron data
;

_refine_ls_R_factor_gt           0.1149
_refine_ls_wR_factor_gt          0.1265
_refine_ls_R_factor_all          0.1230
_refine_ls_wR_factor_all         0.1279
_refine_ls_goodness_of_fit_all   2.59
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_parameters     23
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0365
_refine_ls_shift/su_mean         0.0043
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?

_pd_proc_2theta_range_min        0.502
_pd_proc_2theta_range_max        25
_pd_proc_2theta_range_inc        0.002
_pd_proc_wavelength              ?

_pd_block_diffractogram_id       ?

_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C -0.0001 0.0005 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0016 0.0017 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_restr_distance_atom_site_label_1
_restr_distance_site_symmetry_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
? ? ? ? ? ?

loop_
_restr_angle_atom_site_label_1
_restr_angle_site_symmetry_1
_restr_angle_atom_site_label_2
_restr_angle_site_symmetry_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_torsion_atom_site_label_1
_restr_torsion_site_symmetry_1
_restr_torsion_atom_site_label_2
_restr_torsion_site_symmetry_2
_restr_torsion_atom_site_label_3
_restr_torsion_site_symmetry_3
_restr_torsion_atom_site_label_4
_restr_torsion_site_symmetry_4
_restr_torsion_angle_target
_restr_torsion_weight_param
? ? ? ? ? ? ? ? ? ?

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_site_symmetry_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
? ? ? ? ? ?

loop_
_restr_equal_angle_atom_site_label_1
_restr_equal_angle_site_symmetry_1
_restr_equal_angle_atom_site_label_2
_restr_equal_angle_site_symmetry_2
_restr_equal_angle_atom_site_label_3
_restr_equal_angle_site_symmetry_3
_restr_equal_angle_class_class_id
_restr_equal_angle_class_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_equal_torsion_atom_site_label_1
_restr_equal_torsion_site_symmetry_1
_restr_equal_torsion_atom_site_label_2
_restr_equal_torsion_site_symmetry_2
_restr_equal_torsion_atom_site_label_3
_restr_equal_torsion_site_symmetry_3
_restr_equal_torsion_atom_site_label_4
_restr_equal_torsion_site_symmetry_4
_restr_equal_torsion_class_class_id
_restr_equal_torsion_class_target_weight_param
? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.20661 0.21586 -0.26568 Uiso 0.071(6) 4 1 d . . .
O2 O -0.00176 0.30369 0.03511 Uiso 0.071(6) 4 1 d . . .
O3 O 0.01001 0.20173 0.11177 Uiso 0.071(6) 4 1 d . . .
O4 O 0.25942 0.28077 -0.07777 Uiso 0.071(6) 4 1 d . . .
O5 O 0.38004 0.35253 0.16804 Uiso 0.071(6) 4 1 d . . .
O6 O -0.17945 0.40882 -0.09073 Uiso 0.071(6) 4 1 d . . .
C1 C 0.51537 0.08171 0.03261 Uiso 0.029(6) 4 1 d . . .
C2 C 0.32681 0.1175 0.06791 Uiso 0.029(6) 4 1 d . . .
C3 C 0.29066 0.17189 -0.00113 Uiso 0.029(6) 4 1 d . . .
C4 C 0.11033 0.20984 0.02864 Uiso 0.029(6) 4 1 d . . .
C5 C 0.0419 0.26321 -0.04983 Uiso 0.029(6) 4 1 d . . .
C6 C -0.21904 0.25773 -0.17849 Uiso 0.029(6) 4 1 d . . .
C7 C -0.15411 0.50553 0.25171 Uiso 0.029(6) 4 1 d . . .
C8 C -0.21087 0.4675 0.13256 Uiso 0.029(6) 4 1 d . . .
C9 C 0.02668 0.43303 0.14482 Uiso 0.029(6) 4 1 d . . .
C10 C -0.01175 0.39922 0.02253 Uiso 0.029(6) 4 1 d . . .
C11 C 0.17059 0.34927 0.0426 Uiso 0.029(6) 4 1 d . . .
C12 C 0.24862 0.33813 -0.07743 Uiso 0.029(6) 4 1 d . . .
H2 H 0.54702 0.04339 0.08683 Uiso 0.0345 4 1 d . . .
H3 H 0.71379 0.10098 0.06037 Uiso 0.0345 4 1 d . . .
H1 H 0.44041 0.07312 -0.07639 Uiso 0.0345 4 1 d . . .
H4 H 0.12859 0.0978 0.03956 Uiso 0.0345 4 1 d . . .
H5 H 0.40267 0.12315 0.17832 Uiso 0.0345 4 1 d . . .
H6 H 0.22446 0.16891 -0.11225 Uiso 0.0345 4 1 d . . .
H7 H 0.48699 0.19222 0.02869 Uiso 0.0345 4 1 d . . .
H8 H -0.2572 0.29678 -0.23018 Uiso 0.0345 4 1 d . . .
H9 H -0.38346 0.24843 -0.14814 Uiso 0.0345 4 1 d . . .
H11 H 0.00775 0.53326 0.26111 Uiso 0.0345 4 1 d . . .
H13 H -0.09692 0.48362 0.34803 Uiso 0.0345 4 1 d . . .
H12 H -0.33165 0.52924 0.23825 Uiso 0.0345 4 1 d . . .
H15 H -0.27701 0.48999 0.03707 Uiso 0.0345 4 1 d . . .
H14 H -0.37988 0.44092 0.1251 Uiso 0.0345 4 1 d . . .
H17 H 0.20577 0.45822 0.15943 Uiso 0.0345 4 1 d . . .
H16 H 0.09222 0.4072 0.23497 Uiso 0.0345 4 1 d . . .
H19 H 0.44561 0.3533 -0.06335 Uiso 0.0345 4 1 d . . .
H18 H 0.09759 0.35358 -0.17227 Uiso 0.0345 4 1 d . . .
H10 H -0.1158 0.22849 -0.32376 Uiso 0.0857 4 1 d . . .
H20 H 0.52303 0.32582 0.17774 Uiso 0.0857 4 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_type_symbol
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . . 1.4235 ?
O2 C5 . . 1.4433 ?
O2 C11 . . 1.4613 ?
O3 C4 . . 1.2333 ?
O4 C5 . . 1.4063 ?
O4 C12 . . 1.436 ?
O5 C11 . . 1.3865 ?
O6 C10 . . 1.2257 ?
C1 C2 . . 1.5213 ?
C2 C3 . . 1.5244 ?
C3 C4 . . 1.4908 ?
C4 C5 . . 1.544 ?
C5 C6 . . 1.5549 ?
C7 C8 . . 1.5246 ?
C8 C9 . . 1.5215 ?
C9 C10 . . 1.5049 ?
C10 C11 . . 1.56 ?
C11 C12 . . 1.5325 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O2 C11 . . . 108.62 ?
C5 O4 C12 . . . 105.81 ?
C1 C2 C3 . . . 112.07 ?
C2 C3 C4 . . . 115.78 ?
O3 C4 C3 . . . 124.7 ?
O3 C4 C5 . . . 117.07 ?
C3 C4 C5 . . . 118.23 ?
O2 C5 O4 . . . 106.17 ?
O2 C5 C4 . . . 109.08 ?
O2 C5 C6 . . . 107.52 ?
O4 C5 C4 . . . 109.98 ?
O4 C5 C6 . . . 113.41 ?
C4 C5 C6 . . . 110.49 ?
O1 C6 C5 . . . 112.63 ?
C7 C8 C9 . . . 113.24 ?
C8 C9 C10 . . . 114.84 ?
O6 C10 C9 . . . 123.3 ?
O6 C10 C11 . . . 118.91 ?
C9 C10 C11 . . . 117.79 ?
O2 C11 O5 . . . 111.67 ?
O2 C11 C10 . . . 104.68 ?
O2 C11 C12 . . . 101.41 ?
O5 C11 C10 . . . 109.11 ?
O5 C11 C12 . . . 115.48 ?
C10 C11 C12 . . . 113.77 ?
O4 C12 C11 . . . 102.07 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?
