# 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_me129
_database_code_depnum_ccdc_archive 'CCDC 1980721'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2020-01-29 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;
_audit_creation_date             2019-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
loop_
_audit_author_email
alex@xrlab.ineos.ac.ru
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H8 O5'
_chemical_formula_sum            'C5 H8 O5'
_chemical_formula_weight         148.11
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8512(13)
_cell_length_b                   5.7699(8)
_cell_length_c                   11.7734(16)
_cell_angle_alpha                90
_cell_angle_beta                 102.850(3)
_cell_angle_gamma                90
_cell_volume                     652.45(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3032
_cell_measurement_temperature    120
_cell_measurement_theta_max      31.94
_cell_measurement_theta_min      3.55
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1525 before and 0.0472 after correction. The Ratio of minimum to maximum transmission is 0.8176. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9425
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.054
_diffrn_reflns_theta_min         2.120
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1852
_reflns_number_total             2274
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.1645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0970
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 O4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68452(7) 0.65519(12) 0.81147(6) 0.01616(15) Uani 1 1 d . . . . .
O2 O 0.55466(7) 0.59074(13) 0.72885(6) 0.01827(15) Uani 1 1 d . . . . .
O3 O 0.80617(8) 0.32383(12) 0.77330(6) 0.01901(16) Uani 1 1 d . . . . .
O4 O 0.83160(8) 0.24255(14) 0.89399(7) 0.02402(17) Uani 1 1 d . . . . .
H4 H 0.7471 0.2203 0.8967 0.039(4) Uiso 1 1 d GR . . . .
O5 O 0.43002(8) 0.70677(15) 0.56031(7) 0.02449(18) Uani 1 1 d . . . . .
C1 C 0.80342(9) 0.56900(16) 0.77205(8) 0.01425(17) Uani 1 1 d . . . . .
C2 C 0.79196(10) 0.63248(18) 0.64378(8) 0.01863(19) Uani 1 1 d . . . . .
H2A H 0.7714 0.4919 0.5948 0.022 Uiso 1 1 calc R . . . .
H2B H 0.8813 0.6979 0.6335 0.022 Uiso 1 1 calc R . . . .
C3 C 0.67513(11) 0.81099(18) 0.60616(9) 0.0203(2) Uani 1 1 d . . . . .
H3A H 0.6978 0.9552 0.6520 0.024 Uiso 1 1 calc R . . . .
H3B H 0.6645 0.8492 0.5227 0.024 Uiso 1 1 calc R . . . .
C4 C 0.54322(10) 0.70875(17) 0.62650(8) 0.01756(19) Uani 1 1 d . . . . .
C5 C 0.92423(10) 0.68111(18) 0.85634(9) 0.01987(19) Uani 1 1 d . . . . .
H5A H 0.9192 0.6429 0.9364 0.030 Uiso 1 1 calc GR . . . .
H5B H 0.9196 0.8496 0.8459 0.030 Uiso 1 1 calc GR . . . .
H5C H 1.0121 0.6234 0.8413 0.030 Uiso 1 1 calc GR . . . .

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 0.0144(3) 0.0206(3) 0.0131(3) -0.0012(2) 0.0022(2) 0.0023(2)
O2 0.0135(3) 0.0208(3) 0.0197(3) 0.0023(3) 0.0020(2) -0.0005(2)
O3 0.0226(3) 0.0141(3) 0.0206(3) -0.0002(2) 0.0053(3) 0.0015(3)
O4 0.0215(4) 0.0228(4) 0.0263(4) 0.0110(3) 0.0022(3) 0.0020(3)
O5 0.0196(3) 0.0301(4) 0.0211(4) -0.0048(3) -0.0012(3) 0.0069(3)
C1 0.0146(4) 0.0137(4) 0.0149(4) -0.0001(3) 0.0042(3) 0.0010(3)
C2 0.0182(4) 0.0239(5) 0.0147(4) 0.0010(3) 0.0056(3) 0.0014(4)
C3 0.0227(5) 0.0217(5) 0.0166(4) 0.0053(3) 0.0045(3) 0.0011(4)
C4 0.0192(4) 0.0165(4) 0.0163(4) -0.0019(3) 0.0025(3) 0.0046(3)
C5 0.0182(4) 0.0196(4) 0.0204(4) -0.0014(3) 0.0011(3) -0.0022(3)

_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 O2 1.4722(10) . ?
O1 C1 1.4410(11) . ?
O2 C4 1.3668(12) . ?
O3 O4 1.4641(11) . ?
O3 C1 1.4149(12) . ?
O4 H4 0.8502 . ?
O5 C4 1.2102(12) . ?
C1 C2 1.5336(13) . ?
C1 C5 1.5147(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5345(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.4941(14) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 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 O1 O2 110.44(6) . . ?
C4 O2 O1 110.23(7) . . ?
C1 O3 O4 109.21(7) . . ?
O3 O4 H4 97.3 . . ?
O1 C1 C2 110.34(7) . . ?
O1 C1 C5 102.60(7) . . ?
O3 C1 O1 110.90(7) . . ?
O3 C1 C2 104.24(7) . . ?
O3 C1 C5 114.19(8) . . ?
C5 C1 C2 114.72(8) . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C1 C2 C3 109.32(8) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 C2 108.18(8) . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
O2 C4 C3 115.71(8) . . ?
O5 C4 O2 116.52(9) . . ?
O5 C4 C3 127.61(9) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O5 0.85 1.92 2.7552(12) 165.8 2_646

_shelx_res_file                  
;
TITL me129_a.res in P2(1)/c
REM Old TITL me129 in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.096, Rweak 0.002, Alpha 0.017, Orientation as input
REM Formula found by SHELXT: C5 O5
CELL 0.71073 9.8512 5.7699 11.7734 90 102.85 90
ZERR 4 0.0013 0.0008 0.0016 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H O
UNIT 20 32 20
EQIV $1 1-X,-0.5+Y,1.5-Z

L.S. 4 0 0
PLAN  20
SIZE 0.05 0.2 0.4
TEMP -153.15
HTAB O4 O5_$1
BOND $H
list 4
fmap 2 53
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\me129.hkl">
REM </olex2.extras>

WGHT    0.044800    0.164500
FVAR       1.19185
O1    3    0.684517    0.655193    0.811469    11.00000    0.01437    0.02058 =
         0.01313   -0.00116    0.00220    0.00230
O2    3    0.554659    0.590744    0.728850    11.00000    0.01353    0.02076 =
         0.01972    0.00228    0.00201   -0.00055
O3    3    0.806170    0.323825    0.773296    11.00000    0.02256    0.01411 =
         0.02058   -0.00016    0.00525    0.00146
O4    3    0.831603    0.242552    0.893992    11.00000    0.02152    0.02282 =
         0.02628    0.01097    0.00220    0.00202
AFIX   7  0.8500
H4    2    0.747066    0.220316    0.896711    11.00000    0.03851
AFIX   0
O5    3    0.430018    0.706774    0.560310    11.00000    0.01961    0.03006 =
         0.02113   -0.00480   -0.00116    0.00690
C1    1    0.803419    0.568997    0.772053    11.00000    0.01460    0.01367 =
         0.01491   -0.00005    0.00419    0.00105
C2    1    0.791956    0.632479    0.643780    11.00000    0.01820    0.02389 =
         0.01471    0.00102    0.00562    0.00144
AFIX  23
H2A   2    0.771426    0.491871    0.594773    11.00000   -1.20000
H2B   2    0.881338    0.697936    0.633487    11.00000   -1.20000
AFIX   0
C3    1    0.675134    0.810990    0.606162    11.00000    0.02268    0.02169 =
         0.01660    0.00534    0.00453    0.00110
AFIX  23
H3A   2    0.697793    0.955200    0.652022    11.00000   -1.20000
H3B   2    0.664479    0.849178    0.522662    11.00000   -1.20000
AFIX   0
C4    1    0.543222    0.708754    0.626498    11.00000    0.01921    0.01653 =
         0.01627   -0.00186    0.00254    0.00465
C5    1    0.924228    0.681110    0.856341    11.00000    0.01819    0.01956 =
         0.02036   -0.00139    0.00109   -0.00224
AFIX 137
H5A   2    0.919167    0.642873    0.936396    11.00000   -1.50000
H5B   2    0.919560    0.849645    0.845874    11.00000   -1.50000
H5C   2    1.012119    0.623350    0.841289    11.00000   -1.50000
AFIX   0
HKLF 4

REM  me129_a.res in P2(1)/c
REM R1 =  0.0366 for    1852 Fo > 4sig(Fo)  and  0.0478 for all    2274 data
REM     94 parameters refined using      0 restraints

END

WGHT      0.0454      0.1624

REM Highest difference peak  0.414,  deepest hole -0.253,  1-sigma level  0.050
Q1    1   0.6135  0.7561  0.6190  11.00000  0.05    0.41
Q2    1   0.8052  0.4573  0.7761  11.00000  0.05    0.40
Q3    1   0.7914  0.5996  0.7100  11.00000  0.05    0.36
Q4    1   0.7374  0.7220  0.6260  11.00000  0.05    0.34
Q5    1   0.8586  0.6191  0.8159  11.00000  0.05    0.32
Q6    1   0.7450  0.5891  0.7832  11.00000  0.05    0.27
Q7    1   0.5518  0.6764  0.6783  11.00000  0.05    0.22
Q8    1   0.6793  0.7875  0.7951  11.00000  0.05    0.22
Q9    1   0.8456  0.0926  0.8893  11.00000  0.05    0.21
Q10   1   0.6863  0.5215  0.8400  11.00000  0.05    0.20
Q11   1   0.8328  0.3785  0.8855  11.00000  0.05    0.19
Q12   1   0.4612  0.7240  0.6161  11.00000  0.05    0.19
Q13   1   0.4086  0.5994  0.5767  11.00000  0.05    0.18
Q14   1   0.8194  0.2014  0.7490  11.00000  0.05    0.17
Q15   1   0.4390  0.8465  0.5558  11.00000  0.05    0.17
Q16   1   0.5597  0.4449  0.7248  11.00000  0.05    0.17
Q17   1   0.6823  0.9378  0.6011  11.00000  0.05    0.16
Q18   1   0.6355  0.8480  0.5442  11.00000  0.05    0.16
Q19   1   0.3785  0.7222  0.5785  11.00000  0.05    0.15
Q20   1   0.6330  0.7553  0.4850  11.00000  0.05    0.15
;
_shelx_res_checksum              64292
_olex2_submission_special_instructions 'No special instructions were received'
