# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_15bek39h
_database_code_depnum_ccdc_archive 'CCDC 1586384'
_audit_update_record             
;
2017-11-18 deposited with the CCDC.
2018-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'L-malic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 O5'
_chemical_formula_sum            'C4 H6 O5'
_chemical_formula_weight         134.09

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   5.7343(6)
_cell_length_b                   6.7990(7)
_cell_length_c                   6.9949(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.9610(10)
_cell_angle_gamma                90
_cell_volume                     263.47(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2115
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      28.05

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_F_000             140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6679
_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            4108
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.014
_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             1305
_reflns_number_gt                1269
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.846
_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 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0520P)²+0.0119P] 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 552 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(5)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1305
_refine_ls_number_parameters     90
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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 0.6505(3) 0.1457(2) 0.8157(2) 0.0183(3) Uani 1 1 d D . . . .
H1O H 0.620(5) 0.056(3) 0.890(4) 0.028 Uiso 1 1 d D U . . .
O2 O 0.4457(2) 0.3509(2) 0.96194(19) 0.0160(3) Uani 1 1 d . . . . .
O3 O 0.4527(2) 0.6350(2) 0.6843(2) 0.0181(3) Uani 1 1 d D . . . .
H3O H 0.483(5) 0.674(5) 0.804(2) 0.027 Uiso 1 1 d D U . . .
O4 O 0.8968(2) 0.6721(2) 0.4600(2) 0.0171(3) Uani 1 1 d . . . . .
O5 O 1.0082(3) 0.8539(2) 0.7359(2) 0.0188(3) Uani 1 1 d . . . . .
H5 H 1.033(5) 0.942(4) 0.654(3) 0.028 Uiso 1 1 calc R U . . .
C1 C 0.5565(3) 0.3173(3) 0.8374(3) 0.0143(4) Uani 1 1 d . . . . .
C2 C 0.6071(3) 0.4723(3) 0.6968(3) 0.0136(4) Uani 1 1 d . . . . .
H2 H 0.5800 0.4126 0.5622 0.016 Uiso 1 1 calc R U . . .
C3 C 0.8749(4) 0.5313(3) 0.7703(3) 0.0157(4) Uani 1 1 d . . . . .
H3A H 0.9091 0.5789 0.9085 0.019 Uiso 1 1 calc R U . . .
H3B H 0.9788 0.4157 0.7669 0.019 Uiso 1 1 calc R U . . .
C4 C 0.9285(4) 0.6913(3) 0.6388(3) 0.0148(4) 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 0.0230(7) 0.0125(7) 0.0216(7) 0.0024(6) 0.0095(6) 0.0021(6)
O2 0.0194(6) 0.0139(7) 0.0161(6) 0.0003(6) 0.0070(5) -0.0001(6)
O3 0.0194(7) 0.0166(8) 0.0183(7) 0.0016(6) 0.0053(5) 0.0040(6)
O4 0.0193(7) 0.0160(8) 0.0171(7) 0.0018(6) 0.0065(5) 0.0002(6)
O5 0.0262(7) 0.0144(7) 0.0175(7) -0.0002(6) 0.0085(6) -0.0007(6)
C1 0.0123(8) 0.0154(10) 0.0138(8) -0.0015(7) 0.0010(7) -0.0014(8)
C2 0.0155(9) 0.0129(9) 0.0130(9) 0.0011(7) 0.0045(7) 0.0007(7)
C3 0.0155(9) 0.0154(10) 0.0165(9) 0.0027(8) 0.0049(7) 0.0021(8)
C4 0.0114(8) 0.0142(10) 0.0196(9) 0.0011(8) 0.0053(7) 0.0020(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 1.310(2) . ?
O1 H1O 0.851(13) . ?
O2 C1 1.225(2) . ?
O3 C2 1.406(2) . ?
O3 H3O 0.852(13) . ?
O4 C4 1.223(2) . ?
O5 C4 1.316(3) . ?
O5 H5 0.87(3) . ?
C1 C2 1.520(3) . ?
C2 C3 1.541(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.506(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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 H1O 114(2) . . ?
C2 O3 H3O 103(2) . . ?
C4 O5 H5 109.5 . . ?
O2 C1 O1 123.60(18) . . ?
O2 C1 C2 123.47(19) . . ?
O1 C1 C2 112.89(16) . . ?
O3 C2 C1 111.30(16) . . ?
O3 C2 C3 111.92(15) . . ?
C1 C2 C3 107.78(15) . . ?
O3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C4 C3 C2 109.11(16) . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
O4 C4 O5 123.88(19) . . ?
O4 C4 C3 123.16(18) . . ?
O5 C4 C3 112.95(17) . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.047

_shelx_res_file                  
;

    15bek39h.res created by SHELXL-2014/7


TITL 15bek39h in P2(1)
CELL  0.71073   5.7343   6.7990   6.9949   90.000  104.961   90.000
ZERR    2.000   0.0006   0.0007   0.0007    0.000    0.001    0.000
LATT -1
SYMM -X, 1/2+Y, -Z
SFAC C  H  O
UNIT 8  12  10
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 6
ACTA
BOND $H
HTAB
FMAP 2
PLAN -20
SIZE 0.11 0.16 0.20
TEMP -173.150

DFIX 0.84 0.01 O1 H1O O3 H3O

WGHT    0.052000    0.011900
FVAR       0.65256
O1    3    0.650547    0.145748    0.815707    11.00000    0.02298    0.01253 =
         0.02160    0.00240    0.00951    0.00209
H1O   2    0.620013    0.055558    0.890104    11.00000   -1.50000
O2    3    0.445713    0.350949    0.961944    11.00000    0.01939    0.01391 =
         0.01615    0.00029    0.00701   -0.00011
O3    3    0.452671    0.635010    0.684344    11.00000    0.01944    0.01663 =
         0.01835    0.00158    0.00526    0.00397
H3O   2    0.483334    0.674444    0.803916    11.00000   -1.50000
O4    3    0.896760    0.672072    0.460035    11.00000    0.01929    0.01597 =
         0.01706    0.00177    0.00651    0.00020
O5    3    1.008222    0.853890    0.735934    11.00000    0.02619    0.01436 =
         0.01754   -0.00025    0.00849   -0.00070
AFIX 148
H5    2    1.033440    0.941922    0.653886    11.00000   -1.50000
AFIX   0
C1    1    0.556477    0.317280    0.837417    11.00000    0.01225    0.01543 =
         0.01384   -0.00148    0.00096   -0.00141
C2    1    0.607143    0.472256    0.696837    11.00000    0.01550    0.01286 =
         0.01304    0.00106    0.00451    0.00071
AFIX  13
H2    2    0.580050    0.412555    0.562222    11.00000   -1.20000
AFIX   0
C3    1    0.874882    0.531274    0.770251    11.00000    0.01550    0.01542 =
         0.01650    0.00274    0.00492    0.00208
AFIX  23
H3A   2    0.909083    0.578891    0.908468    11.00000   -1.20000
H3B   2    0.978841    0.415740    0.766929    11.00000   -1.20000
AFIX   0
C4    1    0.928472    0.691277    0.638806    11.00000    0.01140    0.01417 =
         0.01965    0.00108    0.00533    0.00196
HKLF 4

REM  15bek39h in P2(1)
REM R1 =  0.0294 for    1269 Fo > 4sig(Fo)  and  0.0304 for all    1305 data
REM     90 parameters refined using      3 restraints

END

WGHT      0.0465      0.0234

REM Instructions for potential hydrogen bonds
EQIV $1 -x+1, y-1/2, -z+2
HTAB O1 O2_$1
EQIV $2 -x+1, y+1/2, -z+2
HTAB O3 O2_$2
EQIV $3 -x+2, y+1/2, -z+1
HTAB O5 O4_$3
EQIV $4 -x+1, y-1/2, -z+1
HTAB C2 O3_$4
EQIV $5 -x+2, y-1/2, -z+1
HTAB C3 O4_$5

REM Highest difference peak  0.244,  deepest hole -0.166,  1-sigma level  0.047
Q1    1   0.9165  0.6013  0.7040  11.00000  0.05    0.23
Q2    1   0.5726  0.3952  0.7588  11.00000  0.05    0.22
Q3    1   0.7455  0.5145  0.7413  11.00000  0.05    0.17
Q4    1   0.9535  0.8555  0.8292  11.00000  0.05    0.17
Q5    1   0.4649  0.2811  1.0378  11.00000  0.05    0.17
Q6    1   0.4833 -0.0625  0.9656  11.00000  0.05    0.16
Q7    1   0.8900  0.5730  0.3961  11.00000  0.05    0.14
Q8    1   0.7933  0.7323  0.4031  11.00000  0.05    0.13
Q9    1   0.5634  0.3012  1.0143  11.00000  0.05    0.13
Q10   1   0.9835  0.6828  0.9243  11.00000  0.05    0.13
Q11   1   0.7230  0.1571  0.7227  11.00000  0.05    0.13
Q12   1   1.0723  0.8268  0.8550  11.00000  0.05    0.13
Q13   1   0.8564  0.6827  0.5327  11.00000  0.05    0.12
Q14   1   1.0022  0.6711  0.5332  11.00000  0.05    0.12
Q15   1   0.4542  0.4750  0.4693  11.00000  0.05    0.12
Q16   1   0.7385  0.4786  1.0002  11.00000  0.05    0.11
Q17   1   0.3134  0.6110  0.6541  11.00000  0.05    0.11
Q18   1   1.0734  0.9359  0.9376  11.00000  0.05    0.11
Q19   1   0.6080  0.5186  0.9678  11.00000  0.05    0.11
Q20   1   0.5439  0.2027  0.7639  11.00000  0.05    0.11
;
_shelx_res_checksum              80725

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate'
_chemical_properties_physical    Moisture-sensitive
