# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1532105'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 O5'
_chemical_formula_sum            'C7 H10 O5'
_chemical_formula_weight         174.15

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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_
_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                   7.56590(10)
_cell_length_b                   9.9805(2)
_cell_length_c                   10.2418(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     773.37(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3730
_cell_measurement_theta_min      4.3210
_cell_measurement_theta_max      72.1680

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.115
_shelx_estimated_absorpt_T_min   0.768
_shelx_estimated_absorpt_T_max   0.851
_exptl_absorpt_correction_T_min  0.69375
_exptl_absorpt_correction_T_max  1.00000
_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.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_reflns_number            4290
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         6.192
_diffrn_reflns_theta_max         72.264
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1497
_reflns_number_gt                1477
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.995

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.1290P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 584 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1497
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0620
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.54852(17) 0.63093(14) 0.66807(11) 0.0351(3) Uani 1 1 d . . . . .
O2 O 0.67128(14) 0.55178(12) 0.48871(12) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.42619(15) 0.68625(11) 0.48074(11) 0.0263(3) Uani 1 1 d . . . . .
O4 O 0.44709(16) 0.41788(12) 0.30111(11) 0.0265(3) Uani 1 1 d . . . . .
O5 O 0.31536(14) 0.39411(10) 0.50668(10) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.5472(2) 0.62163(16) 0.55131(15) 0.0231(4) Uani 1 1 d . . . . .
C2 C 0.6868(2) 0.57153(18) 0.34911(17) 0.0288(4) Uani 1 1 d . . . . .
H2A H 0.771619 0.506089 0.312402 0.035 Uiso 1 1 calc R U . . .
H2B H 0.731843 0.662782 0.331038 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5095(2) 0.55357(16) 0.28603(16) 0.0259(4) Uani 1 1 d . . . . .
H3 H 0.518385 0.575598 0.191008 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3732(2) 0.64358(17) 0.34940(16) 0.0252(4) Uani 1 1 d . . . . .
H4 H 0.350118 0.723530 0.293076 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2095(2) 0.55629(17) 0.35688(18) 0.0281(4) Uani 1 1 d . . . . .
H5A H 0.138332 0.563293 0.276073 0.034 Uiso 1 1 calc R U . . .
H5B H 0.135031 0.580976 0.432621 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2859(2) 0.41676(17) 0.37273(15) 0.0232(4) Uani 1 1 d . . . . .
H6 H 0.203075 0.348093 0.336478 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3907(2) 0.26522(17) 0.53033(17) 0.0274(4) Uani 1 1 d . . . . .
H7A H 0.404114 0.251622 0.624575 0.041 Uiso 1 1 calc R U . . .
H7B H 0.506701 0.259705 0.488156 0.041 Uiso 1 1 calc R U . . .
H7C H 0.312868 0.195850 0.494505 0.041 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0446(7) 0.0383(7) 0.0224(6) -0.0013(5) -0.0015(5) -0.0119(6)
O2 0.0230(5) 0.0284(6) 0.0302(6) 0.0030(5) -0.0014(5) 0.0009(4)
O3 0.0291(6) 0.0217(6) 0.0282(6) -0.0042(4) -0.0016(5) 0.0030(4)
O4 0.0330(6) 0.0221(6) 0.0244(5) -0.0022(4) 0.0072(5) -0.0033(5)
O5 0.0235(5) 0.0204(6) 0.0210(5) 0.0006(4) 0.0013(4) 0.0008(4)
C1 0.0241(7) 0.0198(8) 0.0253(8) 0.0010(6) -0.0006(6) -0.0069(6)
C2 0.0275(8) 0.0287(9) 0.0304(8) 0.0008(7) 0.0095(7) -0.0024(7)
C3 0.0346(8) 0.0230(8) 0.0201(7) 0.0031(6) 0.0042(6) -0.0043(7)
C4 0.0296(8) 0.0219(8) 0.0239(8) 0.0041(6) -0.0053(6) 0.0007(7)
C5 0.0246(8) 0.0262(9) 0.0335(9) 0.0044(7) -0.0074(7) 0.0011(7)
C6 0.0228(7) 0.0244(8) 0.0224(7) -0.0006(6) -0.0019(6) -0.0022(6)
C7 0.0284(8) 0.0253(8) 0.0284(9) 0.0041(7) 0.0014(6) 0.0053(6)

_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 1.1995(19) . ?
O2 C1 1.333(2) . ?
O2 C2 1.448(2) . ?
O3 C1 1.333(2) . ?
O3 C4 1.4668(19) . ?
O4 C6 1.4233(18) . ?
O4 C3 1.442(2) . ?
O5 C6 1.4082(18) . ?
O5 C7 1.4276(19) . ?
C2 C3 1.500(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.514(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.516(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.516(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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 C2 117.42(13) . . ?
C1 O3 C4 122.99(13) . . ?
C6 O4 C3 110.06(12) . . ?
C6 O5 C7 111.91(12) . . ?
O1 C1 O3 120.58(16) . . ?
O1 C1 O2 120.93(16) . . ?
O3 C1 O2 118.41(14) . . ?
O2 C2 C3 109.68(13) . . ?
O2 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
O2 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
O4 C3 C2 111.03(14) . . ?
O4 C3 C4 106.76(13) . . ?
C2 C3 C4 110.71(13) . . ?
O4 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
C4 C3 H3 109.4 . . ?
O3 C4 C3 112.29(13) . . ?
O3 C4 C5 110.11(13) . . ?
C3 C4 C5 103.71(14) . . ?
O3 C4 H4 110.2 . . ?
C3 C4 H4 110.2 . . ?
C5 C4 H4 110.2 . . ?
C4 C5 C6 102.83(13) . . ?
C4 C5 H5A 111.2 . . ?
C6 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
C6 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
O5 C6 O4 111.57(12) . . ?
O5 C6 C5 108.18(13) . . ?
O4 C6 C5 105.31(13) . . ?
O5 C6 H6 110.5 . . ?
O4 C6 H6 110.5 . . ?
C5 C6 H6 110.5 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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 O3 C1 O1 -156.45(15) . . . . ?
C4 O3 C1 O2 26.6(2) . . . . ?
C2 O2 C1 O1 -165.30(15) . . . . ?
C2 O2 C1 O3 11.6(2) . . . . ?
C1 O2 C2 C3 -51.96(18) . . . . ?
C6 O4 C3 C2 118.80(14) . . . . ?
C6 O4 C3 C4 -1.96(17) . . . . ?
O2 C2 C3 O4 -64.33(17) . . . . ?
O2 C2 C3 C4 54.07(18) . . . . ?
C1 O3 C4 C3 -20.0(2) . . . . ?
C1 O3 C4 C5 94.99(16) . . . . ?
O4 C3 C4 O3 100.04(15) . . . . ?
C2 C3 C4 O3 -20.92(19) . . . . ?
O4 C3 C4 C5 -18.80(17) . . . . ?
C2 C3 C4 C5 -139.77(13) . . . . ?
O3 C4 C5 C6 -89.25(15) . . . . ?
C3 C4 C5 C6 31.09(16) . . . . ?
C7 O5 C6 O4 -63.53(16) . . . . ?
C7 O5 C6 C5 -178.91(12) . . . . ?
C3 O4 C6 O5 -95.06(15) . . . . ?
C3 O4 C6 C5 22.07(16) . . . . ?
C4 C5 C6 O5 86.46(15) . . . . ?
C4 C5 C6 O4 -32.95(16) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031

_shelx_res_file                  
;
TITL SIR92 run in space group P 21 21 21
    s15ab5.res
    created by SHELXL-2016/6 at 10:12:46 on 10-Feb-2017
CELL  1.54184   7.5659   9.9805  10.2418   90.000   90.000   90.000
ZERR     4.00   0.0001   0.0002   0.0002    0.000    0.000    0.000
LATT  -1
SYMM  1/2 - X, - Y, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y, - Z
SYMM  - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    O
UNIT 28 40 20
OMIT     1   1   1
OMIT    -1   1   1
OMIT     0   1   2
FMAP   2
SIZE     0.150   0.200   0.250
ACTA
BOND   $H
PLAN 5
CONF
LIST   4
L.S.   8
TEMP  -123.00
WGHT    0.031300    0.129000
EXTI    0.026915
FVAR      13.67209
O1    3    0.548522    0.630928    0.668067    11.00000    0.04455    0.03827 =
         0.02241   -0.00128   -0.00148   -0.01191
O2    3    0.671277    0.551784    0.488712    11.00000    0.02296    0.02841 =
         0.03021    0.00303   -0.00137    0.00095
O3    3    0.426193    0.686250    0.480739    11.00000    0.02905    0.02169 =
         0.02816   -0.00421   -0.00159    0.00297
O4    3    0.447093    0.417884    0.301106    11.00000    0.03299    0.02212 =
         0.02439   -0.00223    0.00723   -0.00334
O5    3    0.315355    0.394109    0.506682    11.00000    0.02355    0.02039 =
         0.02104    0.00064    0.00125    0.00076
C1    1    0.547231    0.621631    0.551306    11.00000    0.02412    0.01982 =
         0.02525    0.00097   -0.00056   -0.00692
C2    1    0.686759    0.571527    0.349108    11.00000    0.02747    0.02866 =
         0.03036    0.00083    0.00954   -0.00243
AFIX  23
H2A   2    0.771619    0.506089    0.312402    11.00000   -1.20000
H2B   2    0.731843    0.662782    0.331038    11.00000   -1.20000
AFIX   0
C3    1    0.509476    0.553566    0.286029    11.00000    0.03457    0.02304 =
         0.02010    0.00307    0.00417   -0.00434
AFIX  13
H3    2    0.518385    0.575598    0.191008    11.00000   -1.20000
AFIX   0
C4    1    0.373195    0.643580    0.349404    11.00000    0.02964    0.02193 =
         0.02395    0.00408   -0.00526    0.00071
AFIX  13
H4    2    0.350118    0.723530    0.293076    11.00000   -1.20000
AFIX   0
C5    1    0.209532    0.556288    0.356885    11.00000    0.02461    0.02622 =
         0.03346    0.00442   -0.00741    0.00106
AFIX  23
H5A   2    0.138332    0.563293    0.276073    11.00000   -1.20000
H5B   2    0.135031    0.580976    0.432621    11.00000   -1.20000
AFIX   0
C6    1    0.285883    0.416756    0.372730    11.00000    0.02275    0.02443 =
         0.02238   -0.00060   -0.00188   -0.00216
AFIX  13
H6    2    0.203075    0.348093    0.336478    11.00000   -1.20000
AFIX   0
C7    1    0.390662    0.265218    0.530333    11.00000    0.02842    0.02531 =
         0.02841    0.00414    0.00136    0.00527
AFIX 137
H7A   2    0.404114    0.251622    0.624575    11.00000   -1.50000
H7B   2    0.506701    0.259705    0.488156    11.00000   -1.50000
H7C   2    0.312868    0.195850    0.494505    11.00000   -1.50000
AFIX   0
HKLF    4




REM  SIR92 run in space group P 21 21 21
REM R1 =  0.0241 for    1477 Fo > 4sig(Fo)  and  0.0244 for all    1497 data
REM    111 parameters refined using      0 restraints

END

WGHT      0.0313      0.1290

REM Highest difference peak  0.163,  deepest hole -0.150,  1-sigma level  0.031
Q1    1   0.5929  0.5713  0.3240  11.00000  0.05    0.16
Q2    1   0.4435  0.6010  0.3224  11.00000  0.05    0.15
Q3    1   0.2871  0.6037  0.3550  11.00000  0.05    0.13
Q4    1   0.2384  0.4893  0.3602  11.00000  0.05    0.13
Q5    1   0.3761  0.7241  0.3220  11.00000  0.05    0.12
;
_shelx_res_checksum              24719
####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1532104'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 O5'
_chemical_formula_sum            'C7 H10 O5'
_chemical_formula_weight         174.15

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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_
_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                   5.85770(10)
_cell_length_b                   11.00620(10)
_cell_length_c                   11.88280(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     766.096(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7061
_cell_measurement_theta_min      3.7320
_cell_measurement_theta_max      72.3120

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.126
_shelx_estimated_absorpt_T_min   0.766
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_T_min  0.68919
_exptl_absorpt_correction_T_max  1.00000
_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.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_reflns_number            8745
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.479
_diffrn_reflns_theta_max         72.513
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1517
_reflns_number_gt                1504
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²+0.1424P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 593 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1517
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0590
_refine_ls_wR_factor_gt          0.0590
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 1.2344(3) 0.83443(14) 0.70494(13) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.8519(3) 0.76542(14) 0.68975(14) 0.0229(3) Uani 1 1 d . . . . .
H2A H 0.7117 0.7831 0.6462 0.027 Uiso 1 1 calc R U . . .
H2B H 0.8164 0.7759 0.7706 0.027 Uiso 1 1 calc R U . . .
C3 C 0.9246(3) 0.63724(13) 0.66858(13) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.8166 0.5796 0.7060 0.024 Uiso 1 1 calc R U . . .
C4 C 1.1678(3) 0.61469(13) 0.71026(14) 0.0210(3) Uani 1 1 d . . . . .
H4 H 1.1637 0.5546 0.7733 0.025 Uiso 1 1 calc R U . . .
C5 C 1.2911(3) 0.55837(15) 0.60990(15) 0.0251(3) Uani 1 1 d . . . . .
H5A H 1.3939 0.6179 0.5734 0.030 Uiso 1 1 calc R U . . .
H5B H 1.3809 0.4863 0.6329 0.030 Uiso 1 1 calc R U . . .
C6 C 1.0970(3) 0.52302(14) 0.53250(14) 0.0204(3) Uani 1 1 d . . . . .
H6 H 1.1490 0.5219 0.4524 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8433(3) 0.36221(16) 0.49243(15) 0.0310(4) Uani 1 1 d . . . . .
H7A H 0.9033 0.3556 0.4157 0.047 Uiso 1 1 calc R U . . .
H7B H 0.7126 0.4178 0.4930 0.047 Uiso 1 1 calc R U . . .
H7C H 0.7945 0.2819 0.5186 0.047 Uiso 1 1 calc R U . . .
O1 O 1.3707(2) 0.91542(10) 0.71046(10) 0.0254(3) Uani 1 1 d . . . . .
O2 O 1.03043(19) 0.84989(10) 0.65740(10) 0.0213(3) Uani 1 1 d . . . . .
O3 O 1.2832(2) 0.72491(10) 0.74838(10) 0.0259(3) Uani 1 1 d . . . . .
O4 O 0.9303(2) 0.61471(10) 0.54932(9) 0.0219(3) Uani 1 1 d . . . . .
O5 O 1.0170(2) 0.40781(10) 0.56506(10) 0.0246(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0188(7) 0.0188(7) 0.0204(7) -0.0035(6) 0.0019(6) 0.0008(6)
C2 0.0170(7) 0.0196(7) 0.0321(9) -0.0022(7) 0.0048(7) -0.0014(6)
C3 0.0205(7) 0.0168(7) 0.0221(7) 0.0004(6) 0.0011(6) -0.0021(6)
C4 0.0265(8) 0.0143(7) 0.0220(7) 0.0020(6) -0.0042(7) -0.0011(6)
C5 0.0202(7) 0.0247(8) 0.0304(8) -0.0046(7) -0.0030(7) 0.0027(6)
C6 0.0212(7) 0.0168(7) 0.0233(7) -0.0007(6) 0.0004(6) 0.0019(6)
C7 0.0338(9) 0.0270(8) 0.0323(9) -0.0059(7) -0.0030(8) -0.0078(8)
O1 0.0222(5) 0.0224(6) 0.0317(6) -0.0081(5) 0.0046(5) -0.0046(5)
O2 0.0183(5) 0.0164(5) 0.0291(6) 0.0021(5) -0.0010(5) -0.0004(4)
O3 0.0288(6) 0.0178(5) 0.0311(6) -0.0027(5) -0.0130(5) 0.0011(5)
O4 0.0239(6) 0.0195(5) 0.0224(5) -0.0017(4) -0.0052(5) 0.0051(4)
O5 0.0318(6) 0.0165(5) 0.0255(5) -0.0013(5) -0.0044(5) -0.0011(5)

_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
C1 O1 1.1985(19) . ?
C1 O2 1.3325(19) . ?
C1 O3 1.342(2) . ?
C2 O2 1.4511(19) . ?
C2 C3 1.495(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O4 1.4391(18) . ?
C3 C4 1.528(2) . ?
C3 H3 1.0000 . ?
C4 O3 1.4608(18) . ?
C4 C5 1.526(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.513(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O5 1.4061(19) . ?
C6 O4 1.4184(18) . ?
C6 H6 1.0000 . ?
C7 O5 1.425(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
O1 C1 O2 121.71(15) . . ?
O1 C1 O3 120.33(15) . . ?
O2 C1 O3 117.96(14) . . ?
O2 C2 C3 110.77(12) . . ?
O2 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
O4 C3 C2 109.56(12) . . ?
O4 C3 C4 105.64(13) . . ?
C2 C3 C4 111.37(13) . . ?
O4 C3 H3 110.1 . . ?
C2 C3 H3 110.1 . . ?
C4 C3 H3 110.1 . . ?
O3 C4 C5 111.14(13) . . ?
O3 C4 C3 113.39(12) . . ?
C5 C4 C3 104.70(13) . . ?
O3 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
C3 C4 H4 109.2 . . ?
C6 C5 C4 102.94(13) . . ?
C6 C5 H5A 111.2 . . ?
C4 C5 H5A 111.2 . . ?
C6 C5 H5B 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
O5 C6 O4 111.92(13) . . ?
O5 C6 C5 108.37(13) . . ?
O4 C6 C5 104.39(12) . . ?
O5 C6 H6 110.7 . . ?
O4 C6 H6 110.7 . . ?
C5 C6 H6 110.7 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 O2 C2 116.88(12) . . ?
C1 O3 C4 121.86(12) . . ?
C6 O4 C3 106.10(11) . . ?
C6 O5 C7 112.88(13) . . ?

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 C2 C3 O4 -71.07(16) . . . . ?
O2 C2 C3 C4 45.44(17) . . . . ?
O4 C3 C4 O3 111.98(14) . . . . ?
C2 C3 C4 O3 -6.90(18) . . . . ?
O4 C3 C4 C5 -9.34(15) . . . . ?
C2 C3 C4 C5 -128.22(14) . . . . ?
O3 C4 C5 C6 -137.39(13) . . . . ?
C3 C4 C5 C6 -14.60(15) . . . . ?
C4 C5 C6 O5 -85.22(14) . . . . ?
C4 C5 C6 O4 34.21(15) . . . . ?
O1 C1 O2 C2 -158.19(15) . . . . ?
O3 C1 O2 C2 20.97(19) . . . . ?
C3 C2 O2 C1 -56.11(18) . . . . ?
O1 C1 O3 C4 -157.32(15) . . . . ?
O2 C1 O3 C4 23.5(2) . . . . ?
C5 C4 O3 C1 88.16(17) . . . . ?
C3 C4 O3 C1 -29.5(2) . . . . ?
O5 C6 O4 C3 75.26(15) . . . . ?
C5 C6 O4 C3 -41.74(15) . . . . ?
C2 C3 O4 C6 151.88(13) . . . . ?
C4 C3 O4 C6 31.81(15) . . . . ?
O4 C6 O5 C7 69.41(17) . . . . ?
C5 C6 O5 C7 -176.01(13) . . . . ?

_refine_diff_density_max         0.128
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041

_shelx_res_file                  
;

    s15ab7.res created by SHELXL-2014/7


TITL  SIR92 run in space group P 21 21 21
CELL   1.54184    5.8577  11.0062  11.8828  90.000  90.000  90.000
ZERR   4    0.0001   0.0001   0.0001   0.000   0.000   0.000
LATT -1
SYMM  0.50000-X,-Y, 0.50000+Z
SYMM  0.50000+X, 0.50000-Y,-Z
SYMM -X, 0.50000+Y, 0.50000-Z
SFAC    C   H   O
UNIT 28 40 20
LIST 4
TEMP -123
SIZE 0.25 0.18 0.1
L.S.   10
ACTA
BOND   $H
CONF
FMAP   2
PLAN  -10
WGHT    0.029200    0.142400
FVAR      11.61985
C1    1    1.234405    0.834430    0.704936    11.00000    0.01880    0.01875 =
         0.02043   -0.00348    0.00186    0.00081
C2    1    0.851902    0.765417    0.689748    11.00000    0.01695    0.01955 =
         0.03211   -0.00215    0.00476   -0.00140
AFIX  23
H2A   2    0.711701    0.783067    0.646190    11.00000   -1.20000
H2B   2    0.816371    0.775944    0.770614    11.00000   -1.20000
AFIX   0
C3    1    0.924633    0.637241    0.668585    11.00000    0.02050    0.01679 =
         0.02213    0.00042    0.00115   -0.00208
AFIX  13
H3    2    0.816568    0.579648    0.705984    11.00000   -1.20000
AFIX   0
C4    1    1.167801    0.614687    0.710262    11.00000    0.02653    0.01428 =
         0.02204    0.00196   -0.00418   -0.00110
AFIX  13
H4    2    1.163745    0.554563    0.773324    11.00000   -1.20000
AFIX   0
C5    1    1.291078    0.558371    0.609897    11.00000    0.02019    0.02474 =
         0.03041   -0.00465   -0.00299    0.00275
AFIX  23
H5A   2    1.393906    0.617912    0.573424    11.00000   -1.20000
H5B   2    1.380931    0.486343    0.632886    11.00000   -1.20000
AFIX   0
C6    1    1.096985    0.523017    0.532495    11.00000    0.02117    0.01678 =
         0.02329   -0.00067    0.00044    0.00188
AFIX  13
H6    2    1.149046    0.521915    0.452355    11.00000   -1.20000
AFIX   0
C7    1    0.843288    0.362215    0.492429    11.00000    0.03383    0.02696 =
         0.03226   -0.00590   -0.00299   -0.00780
AFIX 137
H7A   2    0.903322    0.355623    0.415692    11.00000   -1.50000
H7B   2    0.712594    0.417799    0.493032    11.00000   -1.50000
H7C   2    0.794540    0.281871    0.518628    11.00000   -1.50000
AFIX   0
O1    3    1.370716    0.915421    0.710458    11.00000    0.02222    0.02240 =
         0.03171   -0.00811    0.00465   -0.00460
O2    3    1.030425    0.849888    0.657402    11.00000    0.01831    0.01642 =
         0.02905    0.00212   -0.00101   -0.00036
O3    3    1.283230    0.724909    0.748384    11.00000    0.02881    0.01778 =
         0.03109   -0.00270   -0.01302    0.00111
O4    3    0.930292    0.614711    0.549322    11.00000    0.02393    0.01947 =
         0.02237   -0.00173   -0.00515    0.00511
O5    3    1.016962    0.407814    0.565058    11.00000    0.03182    0.01650 =
         0.02554   -0.00126   -0.00440   -0.00111
HKLF      4

REM   SIR92 run in space group P 21 21 21
REM R1 =  0.0238 for    1504 Fo > 4sig(Fo)  and  0.0239 for all    1517 data
REM    110 parameters refined using      0 restraints

END

WGHT      0.0292      0.1424

REM Highest difference peak  0.128,  deepest hole -0.173,  1-sigma level  0.041
Q1    1   1.0416  0.6326  0.6910  11.00000  0.05    0.13
Q2    1   1.2145  0.5408  0.5599  11.00000  0.05    0.12
Q3    1   1.4590  0.5181  0.6188  11.00000  0.05    0.11
Q4    1   1.0525  0.5236  0.4425  11.00000  0.05    0.11
Q5    1   1.3520  0.6581  0.5408  11.00000  0.05    0.10
Q6    1   1.3691  0.6467  0.4990  11.00000  0.05    0.10
Q7    1   0.9264  0.2748  0.3290  11.00000  0.05    0.10
Q8    1   1.2279  0.5830  0.6574  11.00000  0.05    0.10
Q9    1   1.5294  0.9037  0.7422  11.00000  0.05    0.09
Q10   1   1.6065  0.6664  0.5014  11.00000  0.05    0.09
;
_shelx_res_checksum              79806
