# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ta_a
_database_code_depnum_ccdc_archive 'CCDC 1934964'
loop_
_audit_author_name
_audit_author_address
Zhou
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2020-02-10 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         'C6 H12 O6'
_chemical_formula_sum            'C6 H12 O6'
_chemical_formula_weight         180.16

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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.7012(2)
_cell_length_b                   7.7746(2)
_cell_length_c                   12.6751(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     758.91(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    8841
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      68.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   0.6552
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.250
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.788
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10058
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.680
_diffrn_reflns_theta_max         68.181
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1378
_reflns_number_gt                1359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0518P)²+0.0813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 545 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1378
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.44285(17) 0.40847(16) 0.37891(10) 0.0269(3) Uani 1 1 d . . . . .
C1 C 0.5216(2) 0.5699(2) 0.39770(15) 0.0256(4) Uani 1 1 d . . . . .
H1 H 0.512576 0.598933 0.472732 0.031 Uiso 1 1 calc R U . . .
O2 O 0.69582(18) 0.5546(2) 0.36942(12) 0.0337(4) Uani 1 1 d . . . . .
H2A H 0.749(2) 0.495(4) 0.416(2) 0.051 Uiso 1 1 calc R U . . .
H7 H 0.221(5) 0.886(4) 0.249(3) 0.071(11) Uiso 1 1 d . . . . .
C2 C 0.4367(2) 0.7100(2) 0.33179(14) 0.0241(4) Uani 1 1 d . . . . .
H2 H 0.458165 0.688940 0.256689 0.029 Uiso 1 1 calc R U . . .
O3 O 0.5047(2) 0.87423(16) 0.36120(12) 0.0309(4) Uani 1 1 d . . . . .
H3A H 0.596(4) 0.8928(17) 0.328(2) 0.046 Uiso 1 1 calc R U . . .
C3 C 0.2415(2) 0.7116(2) 0.35330(16) 0.0270(4) Uani 1 1 d . . . . .
H3 H 0.224626 0.744841 0.427165 0.032 Uiso 1 1 calc R U . . .
O4 O 0.15325(19) 0.83373(19) 0.28957(15) 0.0403(4) Uani 1 1 d . . . . .
C4 C 0.1647(2) 0.5325(2) 0.33899(16) 0.0276(4) Uani 1 1 d . . . . .
H4 H 0.042038 0.534068 0.359593 0.033 Uiso 1 1 calc R U . . .
O5 O 0.17877(19) 0.48169(19) 0.23067(11) 0.0336(4) Uani 1 1 d . . . . .
H5A H 0.094(4) 0.433(4) 0.2137(10) 0.050 Uiso 1 1 calc R U . . .
C5 C 0.2634(2) 0.4074(3) 0.40968(16) 0.0274(4) Uani 1 1 d . . . . .
H5 H 0.253562 0.444738 0.483286 0.033 Uiso 1 1 calc R U . . .
O6 O 0.3076(2) 0.11316(17) 0.46404(13) 0.0388(4) Uani 1 1 d . . . . .
H6 H 0.367(4) 0.053(4) 0.4266(16) 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2020(3) 0.2233(3) 0.40019(18) 0.0352(5) Uani 1 1 d . . . . .
H6A H 0.081889 0.215274 0.422767 0.042 Uiso 1 1 calc R U . . .
H6B H 0.208395 0.186925 0.327098 0.042 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 0.0238(6) 0.0182(6) 0.0387(7) 0.0006(5) 0.0038(5) 0.0005(5)
C1 0.0227(8) 0.0227(9) 0.0314(8) 0.0010(7) 0.0002(7) -0.0013(8)
O2 0.0218(6) 0.0364(8) 0.0429(8) 0.0087(6) -0.0010(5) 0.0017(6)
C2 0.0221(8) 0.0178(7) 0.0324(8) -0.0007(7) 0.0007(7) -0.0024(7)
O3 0.0273(7) 0.0183(7) 0.0472(8) -0.0029(5) 0.0063(6) -0.0050(5)
C3 0.0226(8) 0.0191(9) 0.0393(9) 0.0018(8) 0.0010(7) 0.0017(8)
O4 0.0254(7) 0.0298(8) 0.0657(10) 0.0153(7) -0.0011(7) 0.0052(6)
C4 0.0196(8) 0.0241(9) 0.0390(10) -0.0005(8) 0.0041(8) -0.0025(7)
O5 0.0251(6) 0.0355(8) 0.0402(8) -0.0035(6) -0.0030(6) -0.0053(6)
C5 0.0255(8) 0.0215(9) 0.0352(9) -0.0004(7) 0.0060(7) -0.0028(7)
O6 0.0469(9) 0.0242(7) 0.0454(8) 0.0058(6) 0.0131(7) 0.0032(6)
C6 0.0354(10) 0.0219(9) 0.0483(11) 0.0037(8) 0.0058(9) -0.0049(9)

_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 1.414(2) . ?
O1 C5 1.436(2) . ?
C1 O2 1.394(2) . ?
C1 C2 1.521(2) . ?
C1 H1 0.9800 . ?
O2 H2A 0.85(3) . ?
C2 O3 1.429(2) . ?
C2 C3 1.527(2) . ?
C2 H2 0.9800 . ?
O3 H3A 0.83(3) . ?
C3 O4 1.420(2) . ?
C3 C4 1.523(3) . ?
C3 H3 0.9800 . ?
O4 H7 0.84(4) . ?
C4 O5 1.433(2) . ?
C4 C5 1.526(3) . ?
C4 H4 0.9800 . ?
O5 H5A 0.78(3) . ?
C5 C6 1.512(3) . ?
C5 H5 0.9800 . ?
O6 C6 1.432(3) . ?
O6 H6 0.80(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

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 C5 111.85(14) . . ?
O2 C1 O1 107.09(14) . . ?
O2 C1 C2 109.51(15) . . ?
O1 C1 C2 111.03(14) . . ?
O2 C1 H1 109.7 . . ?
O1 C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
C1 O2 H2A 109.5 . . ?
O3 C2 C1 109.81(14) . . ?
O3 C2 C3 107.88(15) . . ?
C1 C2 C3 109.31(14) . . ?
O3 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C2 O3 H3A 109.5 . . ?
O4 C3 C4 110.94(15) . . ?
O4 C3 C2 112.01(16) . . ?
C4 C3 C2 110.72(15) . . ?
O4 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C3 O4 H7 112(2) . . ?
O5 C4 C3 109.68(15) . . ?
O5 C4 C5 110.43(15) . . ?
C3 C4 C5 108.60(15) . . ?
O5 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
C4 O5 H5A 109.5 . . ?
O1 C5 C6 106.56(15) . . ?
O1 C5 C4 108.46(15) . . ?
C6 C5 C4 113.62(17) . . ?
O1 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
C6 O6 H6 109.5 . . ?
O6 C6 C5 110.08(17) . . ?
O6 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
O6 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?

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
C5 O1 C1 O2 177.56(14) . . . . ?
C5 O1 C1 C2 -62.9(2) . . . . ?
O2 C1 C2 O3 -68.66(19) . . . . ?
O1 C1 C2 O3 173.29(14) . . . . ?
O2 C1 C2 C3 173.17(15) . . . . ?
O1 C1 C2 C3 55.12(19) . . . . ?
O3 C2 C3 O4 63.9(2) . . . . ?
C1 C2 C3 O4 -176.75(16) . . . . ?
O3 C2 C3 C4 -171.72(15) . . . . ?
C1 C2 C3 C4 -52.4(2) . . . . ?
O4 C3 C4 O5 59.63(19) . . . . ?
C2 C3 C4 O5 -65.38(19) . . . . ?
O4 C3 C4 C5 -179.60(15) . . . . ?
C2 C3 C4 C5 55.4(2) . . . . ?
C1 O1 C5 C6 -172.24(15) . . . . ?
C1 O1 C5 C4 65.08(19) . . . . ?
O5 C4 C5 O1 60.2(2) . . . . ?
C3 C4 C5 O1 -60.13(19) . . . . ?
O5 C4 C5 C6 -58.1(2) . . . . ?
C3 C4 C5 C6 -178.42(15) . . . . ?
O1 C5 C6 O6 57.2(2) . . . . ?
C4 C5 C6 O6 176.58(16) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.041

_shelx_res_file                  
;
TITL ta_a.res in P2(1)2(1)2(1)
    ta_a.res
    created by SHELXL-2016/6 at 17:33:42 on 21-Dec-2018
REM Old TITL ta in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.116,  Rweak 0.018,  Alpha 0.002,  Orientation as input
REM Flack x = -0.010 ( 0.190 ) from Parsons' quotients
REM Formula found by SHELXT:  C6 O6
CELL  1.54178   7.7012   7.7746  12.6751   90.000   90.000   90.000
ZERR   4.000   0.0002   0.0002   0.0004    0.000    0.000    0.000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H O
UNIT 24 48 24
ACTA
SIZE 0.22 0.20 0.21
CONF
TEMP 24.070
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 20
WGHT    0.051800    0.081300
FVAR       1.21255
O1    3    0.442848    0.408467    0.378914    11.00000    0.02377    0.01817 =
         0.03871    0.00064    0.00378    0.00048
C1    1    0.521604    0.569886    0.397696    11.00000    0.02271    0.02272 =
         0.03138    0.00102    0.00016   -0.00126
AFIX  13
H1    2    0.512576    0.598933    0.472732    11.00000   -1.20000
AFIX   0
O2    3    0.695820    0.554593    0.369425    11.00000    0.02179    0.03640 =
         0.04291    0.00871   -0.00100    0.00173
AFIX 148
H2A   2    0.749151    0.495475    0.415724    11.00000   -1.50000
AFIX   0
H7    2    0.221466    0.886478    0.249080    11.00000    0.07094
C2    1    0.436666    0.710040    0.331787    11.00000    0.02209    0.01775 =
         0.03240   -0.00068    0.00074   -0.00241
AFIX  13
H2    2    0.458165    0.688940    0.256689    11.00000   -1.20000
AFIX   0
O3    3    0.504685    0.874232    0.361199    11.00000    0.02730    0.01830 =
         0.04723   -0.00290    0.00630   -0.00504
AFIX 148
H3A   2    0.595503    0.892831    0.328110    11.00000   -1.50000
AFIX   0
C3    1    0.241528    0.711573    0.353300    11.00000    0.02257    0.01912 =
         0.03931    0.00179    0.00100    0.00169
AFIX  13
H3    2    0.224626    0.744841    0.427165    11.00000   -1.20000
AFIX   0
O4    3    0.153251    0.833733    0.289574    11.00000    0.02538    0.02980 =
         0.06574    0.01528   -0.00107    0.00524
C4    1    0.164680    0.532545    0.338990    11.00000    0.01964    0.02408 =
         0.03904   -0.00050    0.00407   -0.00252
AFIX  13
H4    2    0.042038    0.534068    0.359593    11.00000   -1.20000
AFIX   0
O5    3    0.178772    0.481685    0.230673    11.00000    0.02505    0.03552 =
         0.04023   -0.00348   -0.00302   -0.00529
AFIX 148
H5A   2    0.094125    0.433416    0.213658    11.00000   -1.50000
AFIX   0
C5    1    0.263441    0.407418    0.409679    11.00000    0.02552    0.02152 =
         0.03524   -0.00042    0.00596   -0.00279
AFIX  13
H5    2    0.253562    0.444738    0.483286    11.00000   -1.20000
AFIX   0
O6    3    0.307594    0.113164    0.464038    11.00000    0.04687    0.02416 =
         0.04543    0.00578    0.01310    0.00317
AFIX 148
H6    2    0.366644    0.053430    0.426630    11.00000   -1.50000
AFIX   0
C6    1    0.201961    0.223339    0.400190    11.00000    0.03538    0.02191 =
         0.04833    0.00375    0.00581   -0.00487
AFIX  23
H6A   2    0.081889    0.215274    0.422767    11.00000   -1.20000
H6B   2    0.208395    0.186925    0.327098    11.00000   -1.20000
REM #####
AFIX   0
HKLF 4




REM  ta_a.res in P2(1)2(1)2(1)
REM R1 =  0.0283 for    1359 Fo > 4sig(Fo)  and  0.0287 for all    1378 data
REM    121 parameters refined using      0 restraints

END

WGHT      0.0445      0.0998

REM Highest difference peak  0.204,  deepest hole -0.140,  1-sigma level  0.041
Q1    1   0.4789  0.6329  0.3619  11.00000  0.05    0.20
Q2    1   0.2103  0.6223  0.3474  11.00000  0.05    0.20
Q3    1   0.2313  0.3204  0.4085  11.00000  0.05    0.17
Q4    1   0.4796  0.7916  0.3558  11.00000  0.05    0.17
Q5    1   0.2202  0.4740  0.3764  11.00000  0.05    0.16
Q6    1   0.4783  0.4822  0.3933  11.00000  0.05    0.16
Q7    1   0.4877  0.3212  0.4005  11.00000  0.05    0.14
Q8    1   0.6998  0.4977  0.2904  11.00000  0.05    0.13
Q9    1   0.3344  0.7097  0.3358  11.00000  0.05    0.13
Q10   1   0.4743  0.9804  0.3634  11.00000  0.05    0.12
Q11   1   0.2062  0.7847  0.3354  11.00000  0.05    0.11
Q12   1   0.3520  0.3949  0.3987  11.00000  0.05    0.11
Q13   1   0.2273  0.4821  0.4531  11.00000  0.05    0.11
Q14   1   0.2439  0.3793  0.4845  11.00000  0.05    0.10
Q15   1   0.7159  0.6235  0.3040  11.00000  0.05    0.10
Q16   1  -0.0239  0.2434  0.3998  11.00000  0.05    0.10
Q17   1   0.5121  0.8515  0.4364  11.00000  0.05    0.10
Q18   1   0.7572  0.6590  0.3844  11.00000  0.05    0.10
Q19   1   0.1634  0.2792  0.5855  11.00000  0.05    0.09
Q20   1   0.2137  0.3632  0.2370  11.00000  0.05    0.09
;
_shelx_res_checksum              96407
####################################################################### 
# 
# 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_a_a
_database_code_depnum_ccdc_archive 'CCDC 1934967'
loop_
_audit_author_name
_audit_author_address
Zhou
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2020-02-10 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         'C5 H12 O4'
_chemical_formula_sum            'C5 H12 O4'
_chemical_formula_weight         136.15

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      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -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_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   6.0826(12)
_cell_length_b                   6.0826(12)
_cell_length_c                   8.792(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     325.31(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1577
_cell_measurement_theta_min      8.87
_cell_measurement_theta_max      67.62

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             148
_exptl_transmission_factor_min   0.6324
_exptl_transmission_factor_max   0.7530
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.029
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   0.821
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1675
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         8.865
_diffrn_reflns_theta_max         67.944
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             304
_reflns_number_gt                290
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_max     1.000
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+0.0457P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         304
_refine_ls_number_parameters     24
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.2533(2) 0.81780(18) 0.4806(2) 0.0514(6) Uani 1 1 d . . . . .
H1 H 0.137(6) 0.773(3) 0.498(4) 0.077 Uiso 1 1 calc R U . . .
C1 C 0.500000 0.500000 0.500000 0.0284(8) Uani 1 4 d S T P . .
C2 C 0.3741(3) 0.6583(3) 0.3966(2) 0.0391(6) Uani 1 1 d . . . . .
H2A H 0.477291 0.732792 0.330144 0.047 Uiso 1 1 calc R U . . .
H2B H 0.273478 0.574971 0.333308 0.047 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 0.0300(8) 0.0285(8) 0.0956(12) 0.0004(8) 0.0038(7) 0.0053(6)
C1 0.0252(10) 0.0252(10) 0.0349(16) 0.000 0.000 0.000
C2 0.0329(10) 0.0356(10) 0.0487(11) 0.0060(7) -0.0027(7) 0.0045(8)

_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 C2 1.423(2) . ?
O1 H1 0.77(4) . ?
C1 C2 1.5298(19) 3_566 ?
C1 C2 1.5298(19) 2_665 ?
C1 C2 1.5298(19) 4_656 ?
C1 C2 1.5298(19) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

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 . . ?
C2 C1 C2 110.68(8) 3_566 2_665 ?
C2 C1 C2 107.07(16) 3_566 4_656 ?
C2 C1 C2 110.68(8) 2_665 4_656 ?
C2 C1 C2 110.68(8) 3_566 . ?
C2 C1 C2 107.07(16) 2_665 . ?
C2 C1 C2 110.68(8) 4_656 . ?
O1 C2 C1 112.29(15) . . ?
O1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
O1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?

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
C2 C1 C2 O1 -58.01(18) 3_566 . . . ?
C2 C1 C2 O1 -178.74(18) 2_665 . . . ?
C2 C1 C2 O1 60.54(18) 4_656 . . . ?

_refine_diff_density_max         0.115
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.031

_shelx_res_file                  
;
TITL a_a.res in I-4
    a_a.res
    created by SHELXL-2016/6 at 09:50:07 on 30-Sep-2018
REM Old TITL a in I-4
REM SHELXT solution in I-4
REM R1 0.183,  Rweak 0.018,  Alpha 0.002,  Orientation as input
REM Flack x =  0.499 ( 0.287 ) from Parsons' quotients
REM Formula found by SHELXT:  C5 O4
CELL  1.54178   6.0826   6.0826   8.7925   90.000   90.000   90.000
ZERR    2.000   0.0012   0.0012   0.0021    0.000    0.000    0.000
LATT -2
SYMM -X, -Y, Z
SYMM Y, -X, -Z
SYMM -Y, X, -Z
SFAC C H O
UNIT 10 24 8
ACTA
size 0.24 0.22 0.20
conf
twin
TEMP 25.100
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 20
WGHT    0.058700    0.045700
BASF   0.09210
FVAR       2.94467
O1    3    0.253280    0.817805    0.480552    11.00000    0.02996    0.02853 =
         0.09565    0.00042    0.00381    0.00532
AFIX 148
H1    2    0.136920    0.773093    0.497586    11.00000   -1.50000
AFIX   0
C1    1    0.500000    0.500000    0.500000    10.25000    0.02516    0.02516 =
         0.03488    0.00000    0.00000    0.00000
C2    1    0.374078    0.658286    0.396596    11.00000    0.03294    0.03564 =
         0.04866    0.00603   -0.00265    0.00452
AFIX  23
H2A   2    0.477291    0.732792    0.330144    11.00000   -1.20000
H2B   2    0.273478    0.574971    0.333308    11.00000   -1.20000
AFIX   0
HKLF 4




REM  a_a.res in I-4
REM R1 =  0.0297 for     290 Fo > 4sig(Fo)  and  0.0354 for all     304 data
REM     24 parameters refined using      0 restraints

END

WGHT      0.0527      0.0490

REM Highest difference peak  0.115,  deepest hole -0.112,  1-sigma level  0.031
Q1    1   0.5000  1.0000  0.4604  10.50000  0.05    0.11
Q2    1   0.0000  1.0000  0.4317  10.50000  0.05    0.11
Q3    1   0.1403  0.5152  0.4365  11.00000  0.05    0.09
Q4    1   0.1403  0.6099  0.5778  11.00000  0.05    0.09
Q5    1   0.1794  0.7227  0.2296  11.00000  0.05    0.06
Q6    1   0.5000  1.0000  0.2500  10.25000  0.05    0.06
Q7    1   0.2711  0.3479  0.2559  11.00000  0.05    0.06
Q8    1   0.2967  0.7497  0.5576  11.00000  0.05    0.05
Q9    1   0.2485  0.9522  0.5766  11.00000  0.05    0.05
Q10   1   0.4031  0.8630  0.2407  11.00000  0.05    0.05
Q11   1   0.1430  0.8540  0.6066  11.00000  0.05    0.04
Q12   1   0.1752  0.8037  0.6463  11.00000  0.05    0.04
Q13   1   0.1524  0.8944  0.4195  11.00000  0.05    0.03
Q14   1   0.4141  0.5732  0.4509  11.00000  0.05    0.03
Q15   1   0.4310  0.6412  0.2518  11.00000  0.05    0.03
Q16   1   0.3038  0.5525  0.2000  11.00000  0.05    0.03
Q17   1   0.2819  0.7411  0.4234  11.00000  0.05    0.03
Q18   1   0.3770  0.5222  0.1719  11.00000  0.05    0.03
Q19   1   0.3227  0.7418  0.2526  11.00000  0.05    0.02
Q20   1   0.5243  0.8791  0.1920  11.00000  0.05    0.02
;
_shelx_res_checksum              21594
####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 1934968'
loop_
_audit_author_name
_audit_author_address
Zhou
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H10 O5'
_chemical_formula_sum            'C5 H10 O5'
_chemical_formula_weight         150.13

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                   5.61070(10)
_cell_length_b                   9.1858(2)
_cell_length_c                   12.5998(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     649.38(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4612
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      68.13

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   0.6693
_exptl_transmission_factor_max   0.7530
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.217
_shelx_estimated_absorpt_T_min   0.759
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4725
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.961
_diffrn_reflns_theta_max         63.674
_diffrn_reflns_theta_full        63.674
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1065
_reflns_number_gt                1061
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1065
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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 0.8466(3) 1.57013(16) 0.50880(11) 0.0256(5) Uani 1 1 d . . . . .
O2 O 1.1825(3) 1.43835(18) 0.45713(13) 0.0268(4) Uani 1 1 d . . . . .
H2A H 1.272455 1.412404 0.514656 0.040 Uiso 1 1 d R U . . .
H7 H 1.016(5) 1.674(3) 0.396(2) 0.023(6) Uiso 1 1 d . . . . .
H6 H 0.775(5) 1.759(3) 0.445(2) 0.028(7) Uiso 1 1 d . . . . .
O3 O 0.8798(3) 1.21386(15) 0.38045(12) 0.0238(5) Uani 1 1 d . . . . .
H3A H 0.997475 1.212924 0.351451 0.036 Uiso 1 1 d R U . . .
O4 O 0.6384(3) 1.38006(19) 0.22535(11) 0.0284(5) Uani 1 1 d . . . . .
H4A H 0.676094 1.402300 0.164593 0.043 Uiso 1 1 calc R U . . .
O5 O 0.7178(3) 1.69349(16) 0.23682(11) 0.0230(4) Uani 1 1 d . . . . .
H5 H 0.595517 1.756665 0.242300 0.034 Uiso 1 1 d R U . . .
C1 C 0.9432(4) 1.4295(2) 0.48629(16) 0.0209(5) Uani 1 1 d . . . . .
H1 H 0.930874 1.369560 0.550376 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7983(4) 1.3578(2) 0.39844(15) 0.0185(5) Uani 1 1 d . . . . .
H2 H 0.633869 1.350421 0.424174 0.022 Uiso 1 1 calc R U . . .
C3 C 0.7924(3) 1.4513(2) 0.29849(16) 0.0172(5) Uani 1 1 d . . . . .
H3 H 0.952984 1.458669 0.268349 0.021 Uiso 1 1 calc R U . . .
C4 C 0.7024(3) 1.6016(2) 0.32809(15) 0.0178(5) Uani 1 1 d . . . . .
H4 H 0.535671 1.594648 0.350715 0.021 Uiso 1 1 calc R U . . .
C5 C 0.8503(4) 1.6656(2) 0.41775(17) 0.0224(5) 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
O1 0.0358(9) 0.0259(9) 0.0149(8) -0.0006(6) -0.0001(6) 0.0070(7)
O2 0.0217(8) 0.0342(9) 0.0245(8) 0.0090(6) -0.0015(5) 0.0033(7)
O3 0.0273(8) 0.0174(8) 0.0266(9) 0.0038(6) 0.0111(7) 0.0019(6)
O4 0.0392(9) 0.0320(9) 0.0141(8) 0.0025(6) -0.0020(6) -0.0196(7)
O5 0.0251(8) 0.0228(8) 0.0211(8) 0.0090(6) 0.0044(6) 0.0077(6)
C1 0.0245(11) 0.0227(10) 0.0156(9) 0.0057(8) 0.0002(8) 0.0055(9)
C2 0.0198(10) 0.0182(10) 0.0174(10) 0.0023(8) 0.0060(8) 0.0007(8)
C3 0.0179(9) 0.0191(10) 0.0145(9) 0.0028(8) 0.0012(7) -0.0030(8)
C4 0.0159(9) 0.0232(10) 0.0142(9) 0.0048(8) 0.0022(8) 0.0028(8)
C5 0.0268(12) 0.0202(10) 0.0203(10) 0.0005(9) -0.0009(9) 0.0026(9)

_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 1.429(3) . ?
O1 C5 1.444(2) . ?
O2 C1 1.394(3) . ?
O2 H2A 0.9149 . ?
O3 C2 1.417(3) . ?
O3 H3A 0.7549 . ?
O4 C3 1.423(3) . ?
O4 H4A 0.8200 . ?
O5 C4 1.429(2) . ?
O5 H5 0.9011 . ?
C1 C2 1.523(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.525(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.516(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.520(3) . ?
C4 H4 0.9800 . ?
C5 H7 0.97(3) . ?
C5 H6 1.02(3) . ?

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 C5 112.68(14) . . ?
C1 O2 H2A 107.9 . . ?
C2 O3 H3A 111.7 . . ?
C3 O4 H4A 109.5 . . ?
C4 O5 H5 105.8 . . ?
O2 C1 O1 111.40(19) . . ?
O2 C1 C2 110.35(17) . . ?
O1 C1 C2 109.43(17) . . ?
O2 C1 H1 108.5 . . ?
O1 C1 H1 108.5 . . ?
C2 C1 H1 108.5 . . ?
O3 C2 C1 110.33(17) . . ?
O3 C2 C3 113.61(16) . . ?
C1 C2 C3 111.58(17) . . ?
O3 C2 H2 107.0 . . ?
C1 C2 H2 107.0 . . ?
C3 C2 H2 107.0 . . ?
O4 C3 C4 112.08(18) . . ?
O4 C3 C2 106.78(16) . . ?
C4 C3 C2 108.47(16) . . ?
O4 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
O5 C4 C3 108.64(15) . . ?
O5 C4 C5 109.68(17) . . ?
C3 C4 C5 110.66(17) . . ?
O5 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
C5 C4 H4 109.3 . . ?
O1 C5 C4 110.37(17) . . ?
O1 C5 H7 106.8(15) . . ?
C4 C5 H7 109.7(15) . . ?
O1 C5 H6 103.7(17) . . ?
C4 C5 H6 110.6(16) . . ?
H7 C5 H6 115(2) . . ?

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
C5 O1 C1 O2 62.3(2) . . . . ?
C5 O1 C1 C2 -60.0(2) . . . . ?
O2 C1 C2 O3 61.5(2) . . . . ?
O1 C1 C2 O3 -175.57(14) . . . . ?
O2 C1 C2 C3 -65.8(2) . . . . ?
O1 C1 C2 C3 57.1(2) . . . . ?
O3 C2 C3 O4 58.9(2) . . . . ?
C1 C2 C3 O4 -175.56(16) . . . . ?
O3 C2 C3 C4 179.92(16) . . . . ?
C1 C2 C3 C4 -54.6(2) . . . . ?
O4 C3 C4 O5 -67.7(2) . . . . ?
C2 C3 C4 O5 174.63(14) . . . . ?
O4 C3 C4 C5 171.81(16) . . . . ?
C2 C3 C4 C5 54.2(2) . . . . ?
C1 O1 C5 C4 60.6(2) . . . . ?
O5 C4 C5 O1 -177.04(14) . . . . ?
C3 C4 C5 O1 -57.2(2) . . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042

_shelx_res_file                  
;
TITL t_a       P 1          R =  New: P212121
    t_a.res
    created by SHELXL-2018/3 at 10:34:16 on 11-Apr-2019
CELL  1.54178    5.6107    9.1858   12.5998    90.000    90.000    90.000
ZERR        4    0.0001    0.0002    0.0003     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 20 40 20
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 5
FMAP 2
PLAN -20
ACTA
size 0.24 0.22 0.20
conf
BOND $H
CONF
TWIN
WGHT    0.100000
BASF   0.34344
FVAR       2.02286
O1    3    0.846643    1.570134    0.508797    11.00000    0.03585    0.02593 =
         0.01490   -0.00065   -0.00011    0.00703
O2    3    1.182475    1.438354    0.457126    11.00000    0.02174    0.03415 =
         0.02453    0.00904   -0.00146    0.00334
AFIX   3
H2A   2    1.272455    1.412404    0.514656    11.00000   -1.50000
AFIX   0
H7    2    1.015712    1.673811    0.395572    11.00000    0.02324
H6    2    0.774753    1.759316    0.445264    11.00000    0.02830
O3    3    0.879755    1.213864    0.380451    11.00000    0.02734    0.01742 =
         0.02661    0.00378    0.01105    0.00193
AFIX   3
H3A   2    0.997475    1.212924    0.351451    11.00000   -1.50000
AFIX   0
O4    3    0.638406    1.380057    0.225345    11.00000    0.03916    0.03197 =
         0.01408    0.00252   -0.00203   -0.01958
AFIX 147
H4A   2    0.676094    1.402300    0.164593    11.00000   -1.50000
AFIX   0
O5    3    0.717757    1.693485    0.236820    11.00000    0.02505    0.02279 =
         0.02108    0.00904    0.00444    0.00772
AFIX   3
H5    2    0.595517    1.756665    0.242300    11.00000   -1.50000
AFIX   0
C1    1    0.943207    1.429539    0.486288    11.00000    0.02447    0.02271 =
         0.01563    0.00566    0.00016    0.00553
AFIX  13
H1    2    0.930874    1.369560    0.550376    11.00000   -1.20000
AFIX   0
C2    1    0.798255    1.357805    0.398441    11.00000    0.01978    0.01824 =
         0.01739    0.00230    0.00600    0.00068
AFIX  13
H2    2    0.633869    1.350421    0.424174    11.00000   -1.20000
AFIX   0
C3    1    0.792410    1.451337    0.298485    11.00000    0.01790    0.01909 =
         0.01447    0.00280    0.00120   -0.00300
AFIX  13
H3    2    0.952984    1.458669    0.268349    11.00000   -1.20000
AFIX   0
C4    1    0.702393    1.601600    0.328086    11.00000    0.01587    0.02318 =
         0.01423    0.00482    0.00224    0.00276
AFIX  13
H4    2    0.535671    1.594648    0.350715    11.00000   -1.20000
AFIX   0
C5    1    0.850323    1.665566    0.417746    11.00000    0.02684    0.02016 =
         0.02031    0.00048   -0.00091    0.00264

HKLF 4




REM  t_a       P 1          R =  New: P212121
REM wR2 = 0.103118, GooF = S = 0.99371, Restrained GooF = 0.99371 for all data
REM R1 = 0.030221 for 1061 Fo > 4sig(Fo) and 0.030791 for all 1065 data
REM 101 parameters refined using 0 restraints

END

WGHT      0.0503      0.1687

REM Highest difference peak  0.232,  deepest hole -0.210,  1-sigma level  0.042
Q1    1   0.9870  1.4182  0.5745  11.00000  0.05    0.23
Q2    1   0.8039  1.3996  0.3437  11.00000  0.05    0.20
Q3    1   0.8535  1.3943  0.4365  11.00000  0.05    0.20
Q4    1   0.7719  1.6232  0.3729  11.00000  0.05    0.15
Q5    1   0.7639  1.5337  0.3039  11.00000  0.05    0.14
Q6    1   0.8856  1.6188  0.4626  11.00000  0.05    0.14
Q7    1   0.8472  1.7680  0.4327  11.00000  0.05    0.14
Q8    1   0.9681  1.6873  0.3822  11.00000  0.05    0.12
Q9    1   1.2303  1.1842  0.3250  11.00000  0.05    0.12
Q10   1   0.8752  1.6038  0.5596  11.00000  0.05    0.12
Q11   1   0.5603  1.5768  0.5265  11.00000  0.05    0.12
Q12   1   0.2878  1.5089  0.2574  11.00000  0.05    0.10
Q13   1   1.0707  1.7956  0.4590  11.00000  0.05    0.10
Q14   1   0.7228  1.4242  0.2407  11.00000  0.05    0.10
Q15   1   0.9235  1.2308  0.5585  11.00000  0.05    0.10
Q16   1   0.7028  1.7808  0.2573  11.00000  0.05    0.10
Q17   1   0.8865  1.7478  0.5798  11.00000  0.05    0.09
Q18   1   0.5487  1.5579  0.3167  11.00000  0.05    0.09
Q19   1   0.6436  1.2084  0.2779  11.00000  0.05    0.09
Q20   1   0.7505  1.8683  0.1940  11.00000  0.05    0.09
;
_shelx_res_checksum              22044
####################################################################### 
# 
# 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_t_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1934969'
loop_
_audit_author_name
_audit_author_address
Zhou
;Shanghai Jiao Tong University
China
;
_audit_update_record             
;
2019-06-18 deposited with the CCDC.	2020-02-10 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         'C6 H12 O6'
_chemical_formula_sum            'C6 H12 O6'
_chemical_formula_weight         180.16

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                   8.091(2)
_cell_length_b                   9.212(2)
_cell_length_c                   10.056(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     749.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4051
_cell_measurement_theta_min      6.52
_cell_measurement_theta_max      68.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   0.5568
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.265
_shelx_estimated_absorpt_T_min   0.786
_shelx_estimated_absorpt_T_max   0.823
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5684
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         6.516
_diffrn_reflns_theta_max         68.303
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1366
_reflns_number_gt                1267
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1366
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1864
_refine_ls_wR_factor_gt          0.1799
_refine_ls_goodness_of_fit_ref   1.327
_refine_ls_restrained_S_all      1.327
_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 0.0056(5) 0.6267(4) 0.5871(3) 0.0234(9) Uani 1 1 d . . . . .
O2 O 0.0334(4) 0.4365(4) 0.4341(3) 0.0230(8) Uani 1 1 d . . . . .
H2A H 0.1152 0.4767 0.3882 0.035 Uiso 1 1 d R U . . .
O3 O -0.0458(5) 0.2311(4) 0.6202(4) 0.0243(9) Uani 1 1 d . . . . .
H6 H 0.0331 0.1989 0.6543 0.037 Uiso 1 1 d R U . . .
O4 O -0.3638(5) 0.3377(4) 0.6979(4) 0.0311(10) Uani 1 1 d . . . . .
H5 H -0.4282 0.2700 0.6485 0.047 Uiso 1 1 d R U . . .
O5 O -0.2640(5) 0.6195(4) 0.7675(4) 0.0327(10) Uani 1 1 d . . . . .
H5C H -0.3423 0.5889 0.8111 0.049 Uiso 1 1 calc R U . . .
O6 O 0.2304(5) 0.5015(4) 0.7565(4) 0.0352(11) Uani 1 1 d . . . . .
H7 H 0.1790 0.5869 0.7872 0.053 Uiso 1 1 d R U . . .
C1 C 0.0454(6) 0.4780(5) 0.5694(5) 0.0181(11) Uani 1 1 d . . . . .
C2 C -0.0763(6) 0.3794(6) 0.6477(4) 0.0199(11) Uani 1 1 d . . . . .
H2 H -0.0594 0.3959 0.7430 0.024 Uiso 1 1 calc R U . . .
C3 C -0.2534(6) 0.4156(6) 0.6141(4) 0.0212(11) Uani 1 1 d . . . . .
H3 H -0.2750 0.3893 0.5212 0.025 Uiso 1 1 calc R U . . .
C4 C -0.2835(6) 0.5780(6) 0.6323(5) 0.0239(12) Uani 1 1 d . . . . .
H4 H -0.3958 0.6018 0.6030 0.029 Uiso 1 1 calc R U . . .
C5 C -0.1603(7) 0.6651(6) 0.5514(5) 0.0273(13) Uani 1 1 d . . . . .
H5A H -0.1775 0.6464 0.4575 0.033 Uiso 1 1 calc R U . . .
H5B H -0.1776 0.7678 0.5671 0.033 Uiso 1 1 calc R U . . .
C6 C 0.2215(6) 0.4651(6) 0.6206(5) 0.0243(12) Uani 1 1 d . . . . .
H6A H 0.2604 0.3665 0.6080 0.029 Uiso 1 1 calc R U . . .
H6B H 0.2929 0.5293 0.5701 0.029 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 0.0232(19) 0.0171(18) 0.0300(17) 0.0016(14) -0.0005(15) -0.0026(16)
O2 0.0214(18) 0.031(2) 0.0166(15) -0.0007(14) 0.0030(13) -0.0017(16)
O3 0.028(2) 0.0127(17) 0.0324(18) 0.0034(14) 0.0006(16) 0.0025(15)
O4 0.028(2) 0.029(2) 0.0361(19) -0.0055(16) 0.0087(18) -0.0128(17)
O5 0.035(2) 0.035(2) 0.0286(18) -0.0138(16) 0.0099(17) -0.0062(19)
O6 0.035(2) 0.029(2) 0.042(2) -0.0134(17) -0.0184(19) 0.0083(18)
C1 0.022(3) 0.014(2) 0.018(2) -0.0029(17) -0.0014(19) 0.001(2)
C2 0.020(2) 0.023(3) 0.016(2) -0.0013(19) -0.0014(17) -0.006(2)
C3 0.022(3) 0.026(3) 0.015(2) -0.0056(18) 0.0019(19) -0.003(2)
C4 0.019(3) 0.023(3) 0.029(2) -0.006(2) -0.002(2) 0.004(2)
C5 0.030(3) 0.029(3) 0.022(2) 0.002(2) -0.005(2) 0.003(2)
C6 0.022(3) 0.022(3) 0.029(2) 0.000(2) -0.003(2) -0.004(2)

_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 1.418(6) . ?
O1 C5 1.434(7) . ?
O2 C1 1.417(5) . ?
O2 H2A 0.8878 . ?
O3 C2 1.415(6) . ?
O3 H6 0.7830 . ?
O4 C3 1.422(6) . ?
O4 H5 0.9525 . ?
O5 C4 1.421(6) . ?
O5 H5C 0.8200 . ?
O6 C6 1.409(5) . ?
O6 H7 0.9419 . ?
C1 C6 1.520(6) . ?
C1 C2 1.553(7) . ?
C2 C3 1.510(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.527(7) . ?
C3 H3 0.9800 . ?
C4 C5 1.516(7) . ?
C4 H4 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

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 C5 114.8(4) . . ?
C1 O2 H2A 109.6 . . ?
C2 O3 H6 115.0 . . ?
C3 O4 H5 111.4 . . ?
C4 O5 H5C 109.5 . . ?
C6 O6 H7 119.6 . . ?
O2 C1 O1 111.4(4) . . ?
O2 C1 C6 111.6(4) . . ?
O1 C1 C6 104.2(4) . . ?
O2 C1 C2 106.6(4) . . ?
O1 C1 C2 111.0(4) . . ?
C6 C1 C2 112.1(4) . . ?
O3 C2 C3 109.5(4) . . ?
O3 C2 C1 110.8(4) . . ?
C3 C2 C1 111.0(4) . . ?
O3 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
O4 C3 C2 110.6(4) . . ?
O4 C3 C4 108.9(4) . . ?
C2 C3 C4 109.9(4) . . ?
O4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
O5 C4 C5 107.4(4) . . ?
O5 C4 C3 111.1(4) . . ?
C5 C4 C3 110.4(4) . . ?
O5 C4 H4 109.3 . . ?
C5 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
O1 C5 C4 110.5(4) . . ?
O1 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
O6 C6 C1 111.0(4) . . ?
O6 C6 H6A 109.4 . . ?
C1 C6 H6A 109.4 . . ?
O6 C6 H6B 109.4 . . ?
C1 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?

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
C5 O1 C1 O2 62.4(5) . . . . ?
C5 O1 C1 C6 -177.1(4) . . . . ?
C5 O1 C1 C2 -56.2(5) . . . . ?
O2 C1 C2 O3 53.1(5) . . . . ?
O1 C1 C2 O3 174.6(4) . . . . ?
C6 C1 C2 O3 -69.3(5) . . . . ?
O2 C1 C2 C3 -68.8(5) . . . . ?
O1 C1 C2 C3 52.7(5) . . . . ?
C6 C1 C2 C3 168.7(4) . . . . ?
O3 C2 C3 O4 64.5(5) . . . . ?
C1 C2 C3 O4 -172.8(4) . . . . ?
O3 C2 C3 C4 -175.3(4) . . . . ?
C1 C2 C3 C4 -52.6(5) . . . . ?
O4 C3 C4 O5 57.2(5) . . . . ?
C2 C3 C4 O5 -64.1(5) . . . . ?
O4 C3 C4 C5 176.2(4) . . . . ?
C2 C3 C4 C5 55.0(5) . . . . ?
C1 O1 C5 C4 58.7(5) . . . . ?
O5 C4 C5 O1 64.7(5) . . . . ?
C3 C4 C5 O1 -56.6(5) . . . . ?
O2 C1 C6 O6 -177.8(4) . . . . ?
O1 C1 C6 O6 61.8(5) . . . . ?
C2 C1 C6 O6 -58.3(5) . . . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.096

_shelx_res_file                  
;

    t_a.res created by SHELXL-2014/7


TITL t_a       P 21 21 21   R =  New: P212121
CELL  1.54178    8.0910    9.2120   10.0560    90.000    90.000    90.000
ZERR        4    0.0020    0.0020    0.0020     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 24 48 24
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 50
size 0.20 0.18 0.16
conf
FMAP 2
PLAN -20
ACTA
BOND $H
CONF
TWIN
REM #####
WGHT    0.100000
BASF   0.38495
FVAR       1.24721
O1    3    0.005600    0.626681    0.587100    11.00000    0.02318    0.01715 =
         0.03000    0.00157   -0.00051   -0.00257
O2    3    0.033407    0.436519    0.434127    11.00000    0.02141    0.03112 =
         0.01659   -0.00074    0.00296   -0.00170
AFIX   3
H2A   2    0.115207    0.476719    0.388227    11.00000   -1.50000
AFIX   0
O3    3   -0.045819    0.231146    0.620217    11.00000    0.02794    0.01271 =
         0.03236    0.00337    0.00064    0.00245
AFIX   3
H6    2    0.033081    0.198946    0.654317    11.00000   -1.50000
AFIX   0
O4    3   -0.363769    0.337715    0.697878    11.00000    0.02791    0.02926 =
         0.03611   -0.00554    0.00871   -0.01282
AFIX   3
H5    2   -0.428169    0.270005    0.648478    11.00000   -1.50000
AFIX   0
O5    3   -0.264029    0.619453    0.767493    11.00000    0.03468    0.03476 =
         0.02859   -0.01385    0.00990   -0.00624
AFIX 147
H5C   2   -0.342299    0.588874    0.811068    11.00000   -1.50000
AFIX   0
O6    3    0.230396    0.501480    0.756532    11.00000    0.03522    0.02873 =
         0.04154   -0.01338   -0.01842    0.00829
AFIX   3
H7    2    0.178996    0.586880    0.787232    11.00000   -1.50000
AFIX   0
C1    1    0.045351    0.477997    0.569443    11.00000    0.02173    0.01408 =
         0.01840   -0.00292   -0.00144    0.00138
C2    1   -0.076269    0.379387    0.647717    11.00000    0.02022    0.02350 =
         0.01586   -0.00127   -0.00144   -0.00558
AFIX  13
H2    2   -0.059441    0.395903    0.743033    11.00000   -1.20000
AFIX   0
C3    1   -0.253446    0.415592    0.614057    11.00000    0.02241    0.02646 =
         0.01459   -0.00565    0.00188   -0.00283
AFIX  13
H3    2   -0.275032    0.389307    0.521235    11.00000   -1.20000
AFIX   0
C4    1   -0.283525    0.578033    0.632291    11.00000    0.01923    0.02321 =
         0.02933   -0.00613   -0.00205    0.00353
AFIX  13
H4    2   -0.395846    0.601777    0.603019    11.00000   -1.20000
AFIX   0
C5    1   -0.160344    0.665059    0.551378    11.00000    0.03046    0.02915 =
         0.02242    0.00226   -0.00480    0.00292
AFIX  23
H5A   2   -0.177547    0.646394    0.457460    11.00000   -1.20000
H5B   2   -0.177577    0.767848    0.567052    11.00000   -1.20000
AFIX   0
C6    1    0.221530    0.465124    0.620640    11.00000    0.02187    0.02175 =
         0.02926   -0.00025   -0.00263   -0.00378
AFIX  23
H6A   2    0.260411    0.366472    0.608038    11.00000   -1.20000
H6B   2    0.292860    0.529310    0.570109    11.00000   -1.20000

AFIX   0
HKLF 4

REM  t_a       P 21 21 21   R =  New: P212121
REM R1 =  0.0656 for    1267 Fo > 4sig(Fo)  and  0.0714 for all    1366 data
REM    111 parameters refined using      0 restraints

END

WGHT      0.0567      0.9769

REM Highest difference peak  0.390,  deepest hole -0.365,  1-sigma level  0.096
Q1    1  -0.1140  0.5070  0.8259  11.00000  0.05    0.39
Q2    1   0.1838  0.3500  0.8615  11.00000  0.05    0.33
Q3    1  -0.2524  0.7818  0.5783  11.00000  0.05    0.33
Q4    1  -0.0559  0.3621  0.8815  11.00000  0.05    0.31
Q5    1   0.2520  0.2793  0.5398  11.00000  0.05    0.29
Q6    1  -0.1503  0.5216  0.3675  11.00000  0.05    0.29
Q7    1  -0.2326  0.2211  0.8557  11.00000  0.05    0.28
Q8    1   0.2151  0.3461  0.4188  11.00000  0.05    0.28
Q9    1   0.0114  0.2773  0.5518  11.00000  0.05    0.27
Q10   1  -0.3036  0.2692  0.5170  11.00000  0.05    0.26
Q11   1   0.0569  0.2568  0.7002  11.00000  0.05    0.26
Q12   1   0.2289  0.3064  0.8194  11.00000  0.05    0.26
Q13   1  -0.3102  0.1563  0.7806  11.00000  0.05    0.25
Q14   1  -0.0488  0.1499  0.5381  11.00000  0.05    0.25
Q15   1  -0.3449  0.4816  0.5220  11.00000  0.05    0.25
Q16   1  -0.0289  0.1648  0.6386  11.00000  0.05    0.25
Q17   1  -0.0727  0.4327  0.3835  11.00000  0.05    0.24
Q18   1  -0.3794  0.3730  0.8656  11.00000  0.05    0.24
Q19   1  -0.1049  0.3355  0.7997  11.00000  0.05    0.23
Q20   1   0.1463  0.1165  0.6383  11.00000  0.05    0.23
;
_shelx_res_checksum              75391
