# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_18bek42h
_database_code_depnum_ccdc_archive 'CCDC 1962561'
loop_
_audit_author_name
_audit_author_address
'Chunhua Tony Hu'
;New York University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2021-03-23 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         ?
_chemical_formula_sum            'C3 H6 O3'
_chemical_formula_weight         90.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   5.7323(3)
_cell_length_b                   9.0190(5)
_cell_length_c                   17.3597(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     897.49(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5183
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.22

_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7101
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14087
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.545
_diffrn_reflns_theta_max         28.294
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2237
_reflns_number_gt                2104
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.998
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0446P)²+0.0360P] 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 826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2237
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.51985(17) 0.67020(12) 0.40602(6) 0.0192(2) Uani 1 1 d . . . . .
O2 O 0.66400(19) 0.54183(14) 0.50523(6) 0.0219(3) Uani 1 1 d . . . . .
H2O H 0.791(4) 0.571(2) 0.4889(12) 0.029(5) Uiso 1 1 d . . . . .
O3 O 0.07304(17) 0.62334(12) 0.45338(6) 0.0177(2) Uani 1 1 d . . . . .
H3O H 0.088(4) 0.595(2) 0.4059(12) 0.026 Uiso 1 1 d . U . . .
C1 C 0.4922(2) 0.59653(15) 0.46383(8) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.2546(2) 0.55395(15) 0.49609(8) 0.0153(3) Uani 1 1 d . . . . .
H2 H 0.245976 0.591705 0.550174 0.018 Uiso 1 1 calc R U . . .
C3 C 0.2263(3) 0.38621(17) 0.49885(9) 0.0220(3) Uani 1 1 d . . . . .
H3A H 0.241816 0.345528 0.446758 0.033 Uiso 1 1 calc R U . . .
H3B H 0.071924 0.361530 0.519436 0.033 Uiso 1 1 calc R U . . .
H3C H 0.346992 0.343593 0.532147 0.033 Uiso 1 1 calc R U . . .
O4 O 0.0645(2) 0.53188(13) 0.30412(6) 0.0230(3) Uani 1 1 d . . . . .
O5 O 0.0528(2) 0.53450(14) 0.17561(6) 0.0254(3) Uani 1 1 d . . . . .
H5O H -0.034(4) 0.460(3) 0.1853(12) 0.037(6) Uiso 1 1 d . . . . .
O6 O 0.2421(2) 0.81550(12) 0.30414(6) 0.0217(2) Uani 1 1 d . . . . .
H6O H 0.314(4) 0.771(2) 0.3380(12) 0.027(5) Uiso 1 1 d . . . . .
C4 C 0.1133(2) 0.58918(17) 0.24282(8) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.2552(3) 0.73106(16) 0.23515(9) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.186329 0.791416 0.192516 0.024 Uiso 1 1 calc R U . . .
C6 C 0.5069(3) 0.6943(2) 0.21371(10) 0.0275(3) Uani 1 1 d . . . . .
H6A H 0.508953 0.635943 0.166103 0.041 Uiso 1 1 calc R U . . .
H6B H 0.579027 0.636986 0.255337 0.041 Uiso 1 1 calc R U . . .
H6C H 0.594445 0.786466 0.205927 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 0.0142(5) 0.0263(5) 0.0171(5) 0.0024(4) -0.0009(4) -0.0015(4)
O2 0.0101(5) 0.0306(6) 0.0251(6) 0.0071(5) -0.0005(4) 0.0011(4)
O3 0.0112(4) 0.0264(6) 0.0154(5) -0.0003(4) -0.0014(4) 0.0024(4)
C1 0.0129(6) 0.0178(6) 0.0160(6) -0.0028(5) 0.0001(5) -0.0007(5)
C2 0.0104(6) 0.0203(7) 0.0152(6) -0.0003(6) -0.0006(5) 0.0008(5)
C3 0.0189(6) 0.0202(7) 0.0268(7) 0.0004(6) 0.0008(6) -0.0013(6)
O4 0.0254(6) 0.0266(5) 0.0170(5) -0.0006(4) -0.0011(4) -0.0053(5)
O5 0.0286(6) 0.0310(6) 0.0166(5) -0.0031(5) 0.0001(4) -0.0095(6)
O6 0.0265(5) 0.0199(5) 0.0187(5) -0.0003(4) -0.0071(5) 0.0030(5)
C4 0.0136(6) 0.0227(7) 0.0184(7) -0.0031(6) -0.0012(5) 0.0018(5)
C5 0.0227(7) 0.0214(7) 0.0157(6) 0.0006(5) -0.0033(6) -0.0009(6)
C6 0.0217(8) 0.0353(8) 0.0255(7) -0.0013(7) 0.0037(6) -0.0061(7)

_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 1.2140(17) . ?
O2 C1 1.3152(17) . ?
O2 H2O 0.82(2) . ?
O3 C2 1.4226(16) . ?
O3 H3O 0.87(2) . ?
C1 C2 1.5220(19) . ?
C2 C3 1.522(2) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
O4 C4 1.2157(18) . ?
O5 C4 1.3133(18) . ?
O5 H5O 0.85(2) . ?
O6 C5 1.4213(18) . ?
O6 H6O 0.82(2) . ?
C4 C5 1.522(2) . ?
C5 C6 1.526(2) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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 H2O 110.9(15) . . ?
C2 O3 H3O 107.2(14) . . ?
O1 C1 O2 124.00(13) . . ?
O1 C1 C2 123.99(12) . . ?
O2 C1 C2 112.00(11) . . ?
O3 C2 C1 110.60(11) . . ?
O3 C2 C3 112.07(11) . . ?
C1 C2 C3 110.95(11) . . ?
O3 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 O5 H5O 106.0(14) . . ?
C5 O6 H6O 108.3(14) . . ?
O4 C4 O5 123.87(14) . . ?
O4 C4 C5 123.85(13) . . ?
O5 C4 C5 112.27(13) . . ?
O6 C5 C4 110.39(12) . . ?
O6 C5 C6 111.82(13) . . ?
C4 C5 C6 110.13(13) . . ?
O6 C5 H5 108.1 . . ?
C4 C5 H5 108.1 . . ?
C6 C5 H5 108.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.037

_shelx_res_file                  
;
TITL 18bek42h in P2(1)2(1)2(1)
    18bek42h.res
    created by SHELXL-2018/3 at 23:25:57 on 06-Apr-2018
CELL 0.71073   5.73230   9.01900  17.35970  90.0000  90.0000  90.0000
ZERR    8.00   0.00030   0.00050   0.00100   0.0000   0.0000   0.0000
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
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
SIZE 0.06 0.29 0.54
TEMP -173.150
OMIT 0 0 2 ! Affected by the beamstop
L.S. 5
ACTA
BOND $H
HTAB
FMAP 2
PLAN -20
WGHT    0.044600    0.036000
FVAR       0.25746
MOLE 1
O1    3    0.519848    0.670203    0.406024    11.00000    0.01423    0.02635 =
         0.01715    0.00235   -0.00089   -0.00146
O2    3    0.664004    0.541831    0.505227    11.00000    0.01010    0.03059 =
         0.02512    0.00715   -0.00054    0.00105
H2O   2    0.791323    0.570540    0.488874    11.00000    0.02862
O3    3    0.073038    0.623338    0.453382    11.00000    0.01116    0.02636 =
         0.01544   -0.00030   -0.00141    0.00236
H3O   2    0.087775    0.595391    0.405946    11.00000   -1.50000
C1    1    0.492189    0.596530    0.463832    11.00000    0.01291    0.01782 =
         0.01599   -0.00283    0.00006   -0.00066
C2    1    0.254557    0.553951    0.496085    11.00000    0.01044    0.02026 =
         0.01517   -0.00030   -0.00055    0.00084
AFIX  13
H2    2    0.245976    0.591705    0.550174    11.00000   -1.20000
AFIX   0
C3    1    0.226306    0.386213    0.498853    11.00000    0.01889    0.02024 =
         0.02681    0.00037    0.00076   -0.00130
AFIX 137
H3A   2    0.241816    0.345528    0.446758    11.00000   -1.50000
H3B   2    0.071924    0.361530    0.519436    11.00000   -1.50000
H3C   2    0.346992    0.343593    0.532147    11.00000   -1.50000
AFIX   0
MOLE 2
O4    3    0.064458    0.531881    0.304124    11.00000    0.02542    0.02664 =
         0.01696   -0.00062   -0.00115   -0.00531
O5    3    0.052830    0.534502    0.175606    11.00000    0.02862    0.03096 =
         0.01664   -0.00310    0.00014   -0.00948
H5O   2   -0.034040    0.459939    0.185281    11.00000    0.03732
O6    3    0.242147    0.815497    0.304143    11.00000    0.02653    0.01989 =
         0.01867   -0.00032   -0.00707    0.00302
H6O   2    0.313505    0.770977    0.337952    11.00000    0.02737
C4    1    0.113292    0.589184    0.242820    11.00000    0.01363    0.02271 =
         0.01840   -0.00309   -0.00125    0.00175
C5    1    0.255245    0.731065    0.235146    11.00000    0.02271    0.02140 =
         0.01572    0.00056   -0.00329   -0.00090
AFIX  13
H5    2    0.186329    0.791416    0.192516    11.00000   -1.20000
AFIX   0
C6    1    0.506943    0.694327    0.213710    11.00000    0.02169    0.03535 =
         0.02546   -0.00131    0.00368   -0.00613
AFIX 137
H6A   2    0.508953    0.635943    0.166103    11.00000   -1.50000
H6B   2    0.579027    0.636986    0.255337    11.00000   -1.50000
H6C   2    0.594445    0.786466    0.205927    11.00000   -1.50000
AFIX   0
HKLF 4




REM  18bek42h in P2(1)2(1)2(1)
REM wR2 = 0.0717, GooF = S = 1.051, Restrained GooF = 1.051 for all data
REM R1 = 0.0283 for 2104 Fo > 4sig(Fo) and 0.0304 for all 2237 data
REM 126 parameters refined using 0 restraints

END

WGHT      0.0449      0.0348

REM Instructions for potential hydrogen bonds
EQIV $1 x+1, y, z
HTAB O2 O3_$1
HTAB O3 O4
EQIV $2 x-1/2, -y+3/2, -z+1
HTAB C2 O1_$2
EQIV $3 -x, y-1/2, -z+1/2
HTAB O5 O6_$3
HTAB O6 O1
EQIV $4 -x, y+1/2, -z+1/2
HTAB C5 O4_$4
HTAB C6 O1

REM Highest difference peak  0.224,  deepest hole -0.171,  1-sigma level  0.037
Q1    1   0.3737  0.5735  0.4805  11.00000  0.05    0.22
Q2    1   0.1834  0.6670  0.2409  11.00000  0.05    0.21
Q3    1   0.2505  0.4705  0.5033  11.00000  0.05    0.16
Q4    1   0.0357  0.6070  0.3390  11.00000  0.05    0.15
Q5    1   0.6411  0.7059  0.3971  11.00000  0.05    0.14
Q6    1  -0.1367  0.3554  0.1846  11.00000  0.05    0.14
Q7    1   0.3754  0.6925  0.2327  11.00000  0.05    0.14
Q8    1   0.0330  0.4378  0.3022  11.00000  0.05    0.13
Q9    1   0.6404  0.6681  0.3834  11.00000  0.05    0.13
Q10   1   0.6524  0.4769  0.5380  11.00000  0.05    0.12
Q11   1   0.3938  0.6835  0.4030  11.00000  0.05    0.11
Q12   1   0.0440  0.5298  0.8069  11.00000  0.05    0.11
Q13   1   0.9572  0.6142  0.4728  11.00000  0.05    0.11
Q14   1   0.3459  0.3084  0.4056  11.00000  0.05    0.11
Q15   1   0.2636  0.6327  0.5401  11.00000  0.05    0.10
Q16   1   0.1206  0.7205  0.4472  11.00000  0.05    0.10
Q17   1   0.1336  0.4457  0.1780  11.00000  0.05    0.10
Q18   1   0.8294  0.6659  0.3944  11.00000  0.05    0.10
Q19   1   0.2482  0.7637  0.2592  11.00000  0.05    0.09
Q20   1  -0.2101  0.4091  0.1949  11.00000  0.05    0.09
;
_shelx_res_checksum              11471

_exptl_crystal_recrystallization_method 'From the Melt'
_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_20bek1h
_database_code_depnum_ccdc_archive 'CCDC 2062531'
loop_
_audit_author_name
_audit_author_address
'Chunhua Tony Hu'
;New York University
United States of America
;
_audit_update_record             
;
2021-02-10 deposited with the CCDC.	2021-03-23 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         ?
_chemical_formula_sum            'C3 H6 O3'
_chemical_formula_weight         90.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   5.4954(4)
_cell_length_b                   8.4298(5)
_cell_length_c                   9.3517(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     433.22(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5150
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.360
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7151
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6736
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.254
_diffrn_reflns_theta_max         28.251
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1081
_reflns_number_gt                1072
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.645
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0527P)²+0.0306P] 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 417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1081
_refine_ls_number_parameters     64
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.058
_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 0.12992(16) 0.40426(11) 0.68051(10) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.38363(15) 0.57229(10) 0.79004(9) 0.0192(2) Uani 1 1 d D . . . .
H2O H 0.263(3) 0.593(2) 0.840(2) 0.046(6) Uiso 1 1 d D . . . .
O3 O 0.44678(15) 0.33782(9) 0.47746(8) 0.0156(2) Uani 1 1 d D . . . .
H3O H 0.551(3) 0.2694(19) 0.453(2) 0.037(5) Uiso 1 1 d D . . . .
C1 C 0.3264(2) 0.46821(12) 0.68963(10) 0.0139(2) Uani 1 1 d . . . . .
C2 C 0.53823(19) 0.43638(13) 0.58910(11) 0.0138(2) Uani 1 1 d . . . . .
H2 H 0.666127 0.376323 0.642535 0.017 Uiso 1 1 calc R U . . .
C3 C 0.6509(2) 0.58831(13) 0.53079(13) 0.0209(2) Uani 1 1 d . . . . .
H3A H 0.784976 0.561560 0.466016 0.031 Uiso 1 1 calc R U . . .
H3B H 0.713137 0.652334 0.610263 0.031 Uiso 1 1 calc R U . . .
H3C H 0.527197 0.648770 0.478598 0.031 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 0.0164(4) 0.0286(5) 0.0240(4) -0.0111(3) 0.0028(3) -0.0052(3)
O2 0.0171(4) 0.0218(4) 0.0186(4) -0.0087(3) 0.0022(3) -0.0030(3)
O3 0.0168(4) 0.0153(4) 0.0146(4) -0.0041(3) -0.0023(3) 0.0041(3)
C1 0.0149(5) 0.0133(5) 0.0134(4) -0.0008(3) -0.0007(4) 0.0016(4)
C2 0.0132(4) 0.0142(4) 0.0139(5) -0.0016(3) -0.0008(4) 0.0011(4)
C3 0.0226(5) 0.0176(5) 0.0224(5) -0.0004(4) 0.0049(4) -0.0034(4)

_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 1.2096(15) . ?
O2 C1 1.3231(13) . ?
O2 H2O 0.833(12) . ?
O3 C2 1.4258(12) . ?
O3 H3O 0.846(12) . ?
C1 C2 1.5203(14) . ?
C2 C3 1.5236(15) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 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 H2O 110.5(15) . . ?
C2 O3 H3O 110.9(14) . . ?
O1 C1 O2 123.91(10) . . ?
O1 C1 C2 124.14(9) . . ?
O2 C1 C2 111.95(10) . . ?
O3 C2 C1 106.60(9) . . ?
O3 C2 C3 111.78(9) . . ?
C1 C2 C3 112.60(9) . . ?
O3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039

_shelx_res_file                  
;
TITL 20bek1h in P2(1)2(1)2(1)
    20bek1h.res
    created by SHELXL-2018/3 at 14:08:49 on 07-Feb-2020
CELL 0.71073   5.49540   8.42980   9.35170  90.0000  90.0000  90.0000
ZERR    4.00   0.00040   0.00050   0.00060   0.0000   0.0000   0.0000
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 12 24 12
TEMP -173.150
SIZE 0.36 0.41 0.54
L.S. 10
ACTA
BOND $H
HTAB
LIST 4
FMAP 2
PLAN -20

DFIX 0.84 0.01 O2 H2O O3 H3O

WGHT    0.052700    0.030600
FVAR       0.63968
O1    3    0.129921    0.404257    0.680514    11.00000    0.01642    0.02860 =
         0.02402   -0.01109    0.00275   -0.00521
O2    3    0.383628    0.572289    0.790042    11.00000    0.01713    0.02178 =
         0.01856   -0.00866    0.00222   -0.00300
H2O   2    0.262798    0.592949    0.840420    11.00000    0.04612
O3    3    0.446778    0.337816    0.477456    11.00000    0.01678    0.01533 =
         0.01458   -0.00409   -0.00233    0.00406
H3O   2    0.551223    0.269375    0.452904    11.00000    0.03721
C1    1    0.326356    0.468213    0.689627    11.00000    0.01490    0.01330 =
         0.01344   -0.00079   -0.00069    0.00161
C2    1    0.538226    0.436376    0.589101    11.00000    0.01323    0.01419 =
         0.01391   -0.00157   -0.00077    0.00110
AFIX  13
H2    2    0.666127    0.376323    0.642535    11.00000   -1.20000
AFIX   0
C3    1    0.650938    0.588313    0.530794    11.00000    0.02256    0.01762 =
         0.02244   -0.00044    0.00492   -0.00341
AFIX 137
H3A   2    0.784976    0.561560    0.466016    11.00000   -1.50000
H3B   2    0.713137    0.652334    0.610263    11.00000   -1.50000
H3C   2    0.527197    0.648770    0.478598    11.00000   -1.50000
AFIX   0
HKLF 4




REM  20bek1h in P2(1)2(1)2(1)
REM wR2 = 0.0708, GooF = S = 1.059, Restrained GooF = 1.058 for all data
REM R1 = 0.0253 for 1072 Fo > 4sig(Fo) and 0.0254 for all 1081 data
REM 64 parameters refined using 2 restraints

END

WGHT      0.0459      0.0439

REM Instructions for potential hydrogen bonds
EQIV $1 -x+1/2, -y+1, z+1/2
HTAB O2 O3_$1
EQIV $2 x+1/2, -y+1/2, -z+1
HTAB O3 O1_$2
HTAB O3 O3_$2
EQIV $3 x+1, y, z
HTAB C2 O1_$3
EQIV $4 -x+1, y-1/2, -z+3/2
HTAB C2 O2_$4
HTAB C2 O3_$2

REM Highest difference peak  0.287,  deepest hole -0.193,  1-sigma level  0.039
Q1    1   0.4297  0.4525  0.6392  11.00000  0.05    0.29
Q2    1   0.5849  0.5106  0.5565  11.00000  0.05    0.16
Q3    1   0.6066  0.3975  0.6312  11.00000  0.05    0.11
Q4    1   0.2360  0.3914  0.7125  11.00000  0.05    0.11
Q5    1   0.7532  0.7821  0.4548  11.00000  0.05    0.10
Q6    1   0.6117  0.6337  0.9311  11.00000  0.05    0.10
Q7    1   0.5679  0.6970  0.5373  11.00000  0.05    0.09
Q8    1   0.6341  0.7988  0.5215  11.00000  0.05    0.09
Q9    1   0.3925  0.5011  0.7778  11.00000  0.05    0.09
Q10   1   0.7940  0.6750  0.7435  11.00000  0.05    0.08
Q11   1   0.5620  0.6557  0.4189  11.00000  0.05    0.08
Q12   1   0.6582  0.3034  0.7017  11.00000  0.05    0.08
Q13   1   0.0349  0.4002  0.7598  11.00000  0.05    0.08
Q14   1   0.3133  0.3225  0.5157  11.00000  0.05    0.08
Q15   1   0.0814  0.3444  0.6156  11.00000  0.05    0.08
Q16   1   1.0755  0.6694  0.4366  11.00000  0.05    0.07
Q17   1  -0.1398  0.3480  0.7739  11.00000  0.05    0.07
Q18   1   0.4637  0.6222  0.3842  11.00000  0.05    0.07
Q19   1   0.1328  0.2863  0.7058  11.00000  0.05    0.07
Q20   1   0.4937  0.3875  0.5364  11.00000  0.05    0.07
;
_shelx_res_checksum              93827

_chemical_properties_physical    Hygroscopic
####################################################################### 
# 
# 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_18bek65h_100K_twin5
_database_code_depnum_ccdc_archive 'CCDC 1962562'
loop_
_audit_author_name
_audit_author_address
'Chunhua Tony Hu'
;New York University
United States of America
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2021-03-23 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         ?
_chemical_formula_sum            'C3 H6 O3'
_chemical_formula_weight         90.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   5.759(3)
_cell_length_b                   5.772(3)
_cell_length_c                   12.492(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     415.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1724
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      26.17

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.933
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.660675
_exptl_absorpt_correction_T_max  0.862013
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1247
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.261
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.620
_diffrn_reflns_point_group_measured_fraction_full 0.621
_reflns_number_total             1247
_reflns_number_gt                1041
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
;
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,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)+(0.0738P)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 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.4(16)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1247
_refine_ls_number_parameters     65
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.062
_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 0.5241(4) 0.7310(4) 0.42773(17) 0.0243(6) Uani 1 1 d . . . . .
O2 O 0.3797(4) 0.4588(5) 0.31826(19) 0.0229(6) Uani 1 1 d D . . . .
H2O H 0.251(5) 0.514(8) 0.338(4) 0.042(13) Uiso 1 1 d D . . . .
O3 O 0.9648(4) 0.6312(4) 0.36031(19) 0.0220(6) Uani 1 1 d D . . . .
H3O H 0.952(8) 0.676(7) 0.4242(15) 0.027(11) Uiso 1 1 d D . . . .
C1 C 0.5497(6) 0.5708(6) 0.3663(3) 0.0196(8) Uani 1 1 d . . . . .
C2 C 0.7848(6) 0.4679(6) 0.3387(3) 0.0193(8) Uani 1 1 d . . . . .
H2 H 0.786791 0.432167 0.260355 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8207(7) 0.2419(7) 0.4000(3) 0.0247(8) Uani 1 1 d . . . . .
H3A H 0.694751 0.133951 0.382823 0.037 Uiso 1 1 calc R U . . .
H3B H 0.820732 0.273558 0.477041 0.037 Uiso 1 1 calc R U . . .
H3C H 0.969772 0.173074 0.379394 0.037 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 0.0207(14) 0.0230(12) 0.0293(13) -0.0041(10) 0.0023(11) 0.0000(12)
O2 0.0120(12) 0.0244(14) 0.0323(13) -0.0042(11) -0.0006(10) -0.0010(11)
O3 0.0165(13) 0.0229(12) 0.0267(14) -0.0023(10) 0.0006(11) -0.0024(11)
C1 0.0193(18) 0.0179(16) 0.0215(16) 0.0041(13) 0.0006(14) 0.0004(14)
C2 0.0152(16) 0.0197(18) 0.0231(17) -0.0016(13) 0.0013(13) -0.0017(16)
C3 0.0216(19) 0.0203(16) 0.0321(17) 0.0013(16) -0.0006(14) 0.0017(17)

_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 1.210(4) . ?
O2 C1 1.318(4) . ?
O2 H2O 0.846(16) . ?
O3 C2 1.427(4) . ?
O3 H3O 0.843(15) . ?
C1 C2 1.519(5) . ?
C2 C3 1.527(5) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 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 H2O 109(3) . . ?
C2 O3 H3O 109(3) . . ?
O1 C1 O2 125.0(3) . . ?
O1 C1 C2 123.5(3) . . ?
O2 C1 C2 111.5(3) . . ?
O3 C2 C1 110.2(3) . . ?
O3 C2 C3 111.8(3) . . ?
C1 C2 C3 109.9(3) . . ?
O3 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.050

_shelx_res_file                  
;
TITL 18bek65h_100K_twin5 in P2(1)2(1)2(1)
    18bek65h_100K_twin5.res
    created by SHELXL-2018/3 at 02:47:35 on 02-Aug-2018
CELL 0.71073   5.75860   5.77230  12.49240  90.0000  90.0000  90.0000
ZERR    4.00   0.00320   0.00320   0.00690   0.0000   0.0000   0.0000
LATT -1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC C H O
UNIT 12 24 12
TEMP -173.150
SIZE 0.04 0.08 0.54
L.S. 6
ACTA
BOND $H
HTAB
LIST 4
FMAP 2
PLAN -20
MERG 0

DFIX 0.84 0.01 O2 H2O O3 H3O

WGHT    0.073800
BASF   0.35085
FVAR       1.68897
O1    3    0.524077    0.730985    0.427728    11.00000    0.02067    0.02298 =
         0.02929   -0.00410    0.00235   -0.00002
O2    3    0.379731    0.458840    0.318258    11.00000    0.01201    0.02435 =
         0.03230   -0.00415   -0.00058   -0.00105
H2O   2    0.250765    0.514006    0.338194    11.00000    0.04154
O3    3    0.964812    0.631218    0.360314    11.00000    0.01655    0.02287 =
         0.02672   -0.00229    0.00056   -0.00244
H3O   2    0.952126    0.676368    0.424231    11.00000    0.02737
C1    1    0.549678    0.570805    0.366346    11.00000    0.01929    0.01793 =
         0.02153    0.00410    0.00065    0.00043
C2    1    0.784843    0.467850    0.338682    11.00000    0.01525    0.01967 =
         0.02308   -0.00155    0.00134   -0.00168
AFIX  13
H2    2    0.786791    0.432167    0.260355    11.00000   -1.20000
AFIX   0
C3    1    0.820737    0.241883    0.399970    11.00000    0.02164    0.02034 =
         0.03213    0.00134   -0.00057    0.00172
AFIX 137
H3A   2    0.694751    0.133951    0.382823    11.00000   -1.50000
H3B   2    0.820732    0.273558    0.477041    11.00000   -1.50000
H3C   2    0.969772    0.173074    0.379394    11.00000   -1.50000
AFIX   0
HKLF 5 1 0 -1 0 1 0 0 0 0 1




REM  18bek65h_100K_twin5 in P2(1)2(1)2(1)
REM wR2 = 0.1226, GooF = S = 1.063, Restrained GooF = 1.062 for all data
REM R1 = 0.0493 for 1041 Fo > 4sig(Fo) and 0.0614 for all 1247 data
REM 65 parameters refined using 2 restraints

END

WGHT      0.0741      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 x-1, y, z
HTAB O2 O3_$1
EQIV $2 x+1/2, -y+3/2, -z+1
HTAB O3 O1_$2
EQIV $3 x, y-1, z
HTAB C3 O1_$3

REM Highest difference peak  0.239,  deepest hole -0.182,  1-sigma level  0.050
Q1    1   0.9622  0.6594  0.3002  11.00000  0.05    0.24
Q2    1   0.5397  0.7273  0.3670  11.00000  0.05    0.23
Q3    1   0.8022  0.3568  0.3607  11.00000  0.05    0.21
Q4    1   0.5233  0.7246  0.4798  11.00000  0.05    0.21
Q5    1   0.3876  0.4621  0.2593  11.00000  0.05    0.20
Q6    1   0.5417  0.8558  0.4309  11.00000  0.05    0.18
Q7    1   0.6702  0.5245  0.3507  11.00000  0.05    0.17
Q8    1   1.1067  0.7614  0.3566  11.00000  0.05    0.16
Q9    1   0.3737  0.3460  0.3754  11.00000  0.05    0.15
Q10   1   0.9667  0.7974  0.3441  11.00000  0.05    0.15
Q11   1   0.4054  0.8344  0.4248  11.00000  0.05    0.15
Q12   1   0.8106  0.2524  0.4521  11.00000  0.05    0.15
Q13   1   0.5388  0.5860  0.4261  11.00000  0.05    0.14
Q14   1   0.5262  0.8668  0.3599  11.00000  0.05    0.14
Q15   1   0.8441  0.5232  0.3400  11.00000  0.05    0.14
Q16   1   1.0800  0.2254  0.4806  11.00000  0.05    0.13
Q17   1   0.3916  0.6254  0.4382  11.00000  0.05    0.13
Q18   1   0.5156  0.5470  0.3150  11.00000  0.05    0.12
Q19   1   0.9706  0.5178  0.3049  11.00000  0.05    0.12
Q20   1   0.1085  0.5485  0.3572  11.00000  0.05    0.12
;
_shelx_res_checksum              46946

_exptl_crystal_recrystallization_method 'From the Melt'
_chemical_properties_physical    Hygroscopic
