# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_1046
_database_code_depnum_ccdc_archive 'CCDC 1481046'
_audit_update_record             
;
2016-05-20 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_audit_creation_date             2016-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 dimethyl (2R,5S,E)-2,5-dihydroxyhex-3-enedioate
;
_chemical_formula_moiety         'C8 H12 O6'
_chemical_formula_sum            'C8 H12 O6'
_chemical_formula_weight         204.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 N10 O10 H10'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.8642(8)
_cell_length_b                   4.0675(3)
_cell_length_c                   14.5155(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.896(8)
_cell_angle_gamma                90
_cell_volume                     460.96(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1580
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      61.9150
_cell_measurement_theta_min      5.6220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.369
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.065
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.867
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2509
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.182
_diffrn_reflns_theta_min         5.667
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3073
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.867
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -26.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega   50.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   76.0000  161.1919 30

#__ type_ start__ end____ width___ exp.time_
  3 omega   60.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   45.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   97.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   77.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega  123.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   77.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega  100.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811  125.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega  104.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   77.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
  8 omega  102.00  156.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   77.0000 -150.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   64.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   45.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 10 omega   55.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   61.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   58.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   50.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   77.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   56.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   59.0000 -156.5093 26

#__ type_ start__ end____ width___ exp.time_
 14 omega    9.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 15 omega  -63.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega   53.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   61.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
 17 omega   50.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   50.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   75.0000  146.7648 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   50.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811   77.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega    7.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811  -77.0000   30.0000 108

#__ type_ start__ end____ width___ exp.time_
 21 omega   84.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811 -125.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
 22 omega   23.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       82.2811 -125.0000    0.0000 55

#__ type_ start__ end____ width___ exp.time_
 23 omega  -67.00  -38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000 -178.0000 -120.0000 29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1548777000
_diffrn_orient_matrix_UB_12      -0.1027747000
_diffrn_orient_matrix_UB_13      0.0692151000
_diffrn_orient_matrix_UB_21      0.1162644000
_diffrn_orient_matrix_UB_22      0.0188114000
_diffrn_orient_matrix_UB_23      -0.0779459000
_diffrn_orient_matrix_UB_31      0.0378064000
_diffrn_orient_matrix_UB_32      0.3642186000
_diffrn_orient_matrix_UB_33      0.0235699000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                644
_reflns_number_total             721
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.268
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         721
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.268
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0485P)²+1.6038P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.1685
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O2 O 0.7675(3) 0.0844(7) 0.79698(17) 0.0188(7) Uani 1 1 d . . . . .
O1 O 0.4357(3) -0.0174(7) 0.82722(17) 0.0163(7) Uani 1 1 d . . . . .
H1 H 0.3947 -0.1391 0.7853 0.024 Uiso 1 1 calc GR . . . .
O3 O 0.8612(3) -0.2676(7) 0.91054(17) 0.0156(7) Uani 1 1 d . . . . .
C3 C 0.7396(5) -0.1041(9) 0.8576(2) 0.0129(8) Uani 1 1 d . . . . .
C1 C 0.5569(4) -0.1012(9) 0.9853(2) 0.0119(8) Uani 1 1 d . . . . .
H1A H 0.6378 -0.1962 1.0293 0.014 Uiso 1 1 calc R . . . .
C2 C 0.5629(4) -0.1866(9) 0.8847(2) 0.0120(8) Uani 1 1 d . . . . .
H2 H 0.5433 -0.4233 0.8766 0.014 Uiso 1 1 calc R . . . .
C4 C 1.0347(5) -0.2163(11) 0.8883(3) 0.0208(10) Uani 1 1 d . . . . .
H4A H 1.0446 -0.3021 0.8276 0.031 Uiso 1 1 calc GR . . . .
H4B H 1.1141 -0.3277 0.9332 0.031 Uiso 1 1 calc GR . . . .
H4C H 1.0599 0.0147 0.8895 0.031 Uiso 1 1 calc GR . . . .


_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
O2 C3 1.206(5) . ?
O1 H1 0.8200 . ?
O1 C2 1.404(4) . ?
O3 C3 1.331(4) . ?
O3 C4 1.454(4) . ?
C3 C2 1.526(5) . ?
C1 C1 1.323(7) 3_657 ?
C1 H1A 0.9300 . ?
C1 C2 1.508(5) . ?
C2 H2 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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
C2 O1 H1 109.5 . . ?
C3 O3 C4 115.3(3) . . ?
O2 C3 O3 123.9(3) . . ?
O2 C3 C2 125.3(3) . . ?
O3 C3 C2 110.7(3) . . ?
C1 C1 H1A 118.1 3_657 . ?
C1 C1 C2 123.8(4) 3_657 . ?
C2 C1 H1A 118.1 . . ?
O1 C2 C3 110.2(3) . . ?
O1 C2 C1 111.1(3) . . ?
O1 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C1 C2 C3 109.6(3) . . ?
C1 C2 H2 108.7 . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 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
O2 C3 C2 O1 1.5(5) . . . . ?
O2 C3 C2 C1 -121.0(4) . . . . ?
O3 C3 C2 O1 -178.9(3) . . . . ?
O3 C3 C2 C1 58.6(4) . . . . ?
C1 C1 C2 O1 1.5(6) 3_657 . . . ?
C1 C1 C2 C3 123.5(5) 3_657 . . . ?
C4 O3 C3 O2 -2.6(5) . . . . ?
C4 O3 C3 C2 177.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
