# 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_mo_PL_LLOH14_0m
_database_code_depnum_ccdc_archive 'CCDC 1836394'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '1,4-Butanedioic acid'
_chemical_name_common            'succinic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 O4'
_chemical_formula_sum            'C4 H6 O4'
_chemical_formula_weight         118.09

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   5.7015(5)
_cell_length_b                   8.4154(8)
_cell_length_c                   10.3538(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.374(3)
_cell_angle_gamma                90
_cell_volume                     496.77(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2129
_cell_measurement_theta_min      4.32
_cell_measurement_theta_max      27.09

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6938
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
'Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11388
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.1089
_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       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.936
_diffrn_reflns_theta_max         29.202
_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             671
_reflns_number_gt                509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²+0.6686P] 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_number_reflns         671
_refine_ls_number_parameters     40
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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 0.89787(19) 0.39490(15) 0.40051(11) 0.0223(3) Uani 1 1 d . . . . .
H1 H 0.922(3) 0.323(2) 0.463(2) 0.027 Uiso 1 1 d . U . . .
O2 O 0.52212(19) 0.32310(14) 0.41820(11) 0.0225(3) Uani 1 1 d . . . . .
C1 C 0.6738(3) 0.40725(18) 0.37068(14) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.6256(3) 0.53659(19) 0.27490(15) 0.0165(3) Uani 1 1 d . . . . .
H2A H 0.7332 0.5242 0.2009 0.020 Uiso 1 1 calc R U . . .
H2B H 0.6592 0.6405 0.3158 0.020 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(6) 0.0279(7) 0.0227(6) 0.0074(5) -0.0038(5) -0.0021(5)
O2 0.0182(6) 0.0238(6) 0.0255(6) 0.0085(5) -0.0021(5) -0.0033(5)
C1 0.0175(7) 0.0150(7) 0.0118(7) -0.0049(6) 0.0002(5) -0.0014(6)
C2 0.0185(8) 0.0150(8) 0.0160(7) -0.0009(6) 0.0007(6) -0.0019(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3166(18) . ?
O1 H1 0.90(2) . ?
O2 C1 1.2235(19) . ?
C1 C2 1.497(2) . ?
C2 C2 1.519(3) 2_655 ?
C2 H2A 0.9900 . ?
C2 H2B 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 H1 111.5(12) . . ?
O2 C1 O1 123.18(15) . . ?
O2 C1 C2 124.08(14) . . ?
O1 C1 C2 112.74(13) . . ?
C1 C2 C2 113.17(12) . 2_655 ?
C1 C2 H2A 108.9 . . ?
C2 C2 H2A 108.9 2_655 . ?
C1 C2 H2B 108.9 . . ?
C2 C2 H2B 108.9 2_655 . ?
H2A C2 H2B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C2 -9.4(2) . . . 2_655 ?
O1 C1 C2 C2 171.66(14) . . . 2_655 ?

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
O1 H1 O2 0.90(2) 1.76(2) 2.6619(16) 177.5(19) 7_656
C2 H2A O1 0.99 2.60 3.4880(19) 149.8 2_755

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.058

_shelx_res_file                  
;

    mo_PL_LLOH14_0m.res created by SHELXL-2014/7


TITL mo_PL_LLOH14_triclinic_0m_a.res in C2/c
REM Old TITL mo_PL_LLOH14_triclinic_0m in C2/c
REM SHELXT solution in C2/c
REM R1 0.110,  Rweak 0.015,  Alpha 0.034,  Orientation as input
REM Formula found by SHELXT:  C2 O2
TITL mo_PL_LLOH14_triclinic_0m in C2/c
CELL 0.71073   5.70150   8.41540  10.35380  90.0000  90.3737  90.0000
ZERR    4.00   0.00050   0.00080   0.00080   0.0000   0.0032   0.0000
LATT  7
SYMM -X, Y, 0.5-Z
SFAC C H O
UNIT 16 24 16
TEMP -100.150
SIZE 0.023 0.077 0.143
ACTA
CONF
HTAB
EQIV $1 -x+3/2, -y+1/2, -z+1
HTAB O1 O2_$1
EQIV $2 -x+2, y, -z+1/2
HTAB C2 O1_$2
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 5
WGHT    0.025100    0.668600
FVAR       0.29482
O1    3    0.897867    0.394896    0.400514    11.00000    0.01636    0.02789 =
         0.02269    0.00742   -0.00379   -0.00207
H1    2    0.922103    0.322643    0.463368    11.00000   -1.20000
O2    3    0.522118    0.323096    0.418198    11.00000    0.01820    0.02377 =
         0.02554    0.00852   -0.00212   -0.00327
C1    1    0.673784    0.407253    0.370676    11.00000    0.01751    0.01503 =
         0.01182   -0.00489    0.00022   -0.00137
C2    1    0.625622    0.536588    0.274903    11.00000    0.01852    0.01497 =
         0.01596   -0.00093    0.00070   -0.00185
AFIX  23
H2A   2    0.733170    0.524245    0.200894    11.00000   -1.20000
H2B   2    0.659218    0.640511    0.315836    11.00000   -1.20000
AFIX   0
HKLF 4

REM  mo_PL_LLOH14_triclinic_0m in C2/c
REM R1 =  0.0472 for     509 Fo > 4sig(Fo)  and  0.0734 for all     671 data
REM     40 parameters refined using      0 restraints

END

WGHT      0.0251      0.6686

REM Instructions for potential hydrogen bonds
HTAB O1 O2_$1
HTAB C2 O1_$2

REM Highest difference peak  0.317,  deepest hole -0.220,  1-sigma level  0.058
Q1    1   0.5000  0.5314  0.2500  10.50000  0.05    0.32
Q2    1   0.6746  0.4525  0.3017  11.00000  0.05    0.21
Q3    1   0.5977  0.3186  0.5011  11.00000  0.05    0.20
Q4    1   0.6762  0.4958  0.3404  11.00000  0.05    0.19
Q5    1   0.9636  0.6786  0.2442  11.00000  0.05    0.17
;
_shelx_res_checksum              11145

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_PL_SAE07b
_database_code_depnum_ccdc_archive 'CCDC 1836683'
_audit_update_record             
;
2018-04-12 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        'mono-methyl hydrogen succinate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H8 O4'
_chemical_formula_sum            'C5 H8 O4'
_chemical_formula_weight         132.11

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.3126(5)
_cell_length_b                   5.5869(3)
_cell_length_c                   9.6891(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.866(2)
_cell_angle_gamma                90
_cell_volume                     611.61(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4500
_cell_measurement_theta_min      3.91
_cell_measurement_theta_max      72.08
_exptl_crystal_description       plate

_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.029
_exptl_absorpt_coefficient_mu    1.093
_shelx_estimated_absorpt_T_min   0.767
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_T_max  0.7536
_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_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6190
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.912
_diffrn_reflns_theta_max         72.073
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1191
_reflns_number_gt                1085
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2018/1 (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)+(0.0363P)²+0.4749P] 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_number_reflns         1191
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_restrained_S_all      1.257
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 1.00 0.0440
-1.00 1.00 -1.00 0.0400
0.00 0.00 -1.00 0.0300
0.00 1.00 -1.00 0.0430
0.00 -1.00 0.00 0.0240
0.00 1.00 0.00 0.0660
0.00 -1.00 -1.00 0.0070
0.00 1.00 1.00 0.0830
-1.00 -1.00 1.00 0.0490
-1.00 -1.00 0.00 0.0260
-1.00 0.00 0.00 0.0140
1.00 0.00 0.00 0.0040

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 0.04326(13) 0.2322(3) 0.09762(15) 0.0261(4) Uani 1 1 d . . . . .
H1 H 0.054(3) -0.164(5) 0.049(3) 0.031 Uiso 1 1 d . U . . .
O2 O 0.10587(15) -0.1462(3) 0.11723(17) 0.0280(4) Uani 1 1 d . . . . .
O3 O 0.33189(15) 0.3190(3) 0.09572(16) 0.0316(4) Uani 1 1 d . . . . .
O4 O 0.35954(13) 0.6587(3) 0.21583(15) 0.0245(4) Uani 1 1 d . . . . .
C1 C 0.10371(17) 0.0792(4) 0.1574(2) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.17941(18) 0.1271(4) 0.2865(2) 0.0217(5) Uani 1 1 d . . . . .
H2A H 0.249002 0.019546 0.287910 0.026 Uiso 1 1 calc R U . . .
H2B H 0.133462 0.088211 0.367825 0.026 Uiso 1 1 calc R U . . .
C3 C 0.22223(18) 0.3845(4) 0.2988(2) 0.0212(5) Uani 1 1 d . . . . .
H3A H 0.153475 0.493753 0.288059 0.025 Uiso 1 1 calc R U . . .
H3B H 0.260005 0.410079 0.391973 0.025 Uiso 1 1 calc R U . . .
C4 C 0.30912(17) 0.4441(4) 0.1920(2) 0.0202(4) Uani 1 1 d . . . . .
C5 C 0.4376(2) 0.7409(4) 0.1119(3) 0.0324(5) Uani 1 1 d . . . . .
H5A H 0.460653 0.907140 0.131222 0.049 Uiso 1 1 calc R U . . .
H5B H 0.396656 0.731337 0.020551 0.049 Uiso 1 1 calc R U . . .
H5C H 0.508530 0.639896 0.113578 0.049 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 0.0296(8) 0.0198(8) 0.0279(8) 0.0009(6) -0.0073(6) 0.0022(6)
O2 0.0365(9) 0.0184(8) 0.0281(8) -0.0016(6) -0.0098(7) 0.0013(6)
O3 0.0403(9) 0.0288(9) 0.0263(8) -0.0101(7) 0.0090(7) -0.0080(7)
O4 0.0251(7) 0.0188(8) 0.0298(8) -0.0046(6) 0.0027(6) -0.0012(6)
C1 0.0203(9) 0.0162(10) 0.0202(9) 0.0028(8) 0.0044(7) -0.0011(8)
C2 0.0260(10) 0.0205(11) 0.0185(10) 0.0012(8) -0.0008(7) 0.0006(8)
C3 0.0253(10) 0.0206(11) 0.0175(9) -0.0023(8) -0.0008(8) 0.0026(8)
C4 0.0216(9) 0.0198(10) 0.0186(9) -0.0023(8) -0.0038(7) 0.0015(8)
C5 0.0328(12) 0.0268(12) 0.0383(13) -0.0020(10) 0.0072(9) -0.0059(10)

_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 1.223(2) . ?
O2 C1 1.319(3) . ?
O2 H1 0.87(3) . ?
O3 C4 1.204(3) . ?
O4 C4 1.343(3) . ?
O4 C5 1.447(3) . ?
C1 C2 1.504(3) . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.500(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
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 O2 H1 108.3(19) . . ?
C4 O4 C5 115.62(17) . . ?
O1 C1 O2 123.10(19) . . ?
O1 C1 C2 123.45(19) . . ?
O2 C1 C2 113.41(17) . . ?
C1 C2 C3 113.56(17) . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 111.91(17) . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O3 C4 O4 123.12(19) . . ?
O3 C4 C3 125.36(19) . . ?
O4 C4 C3 111.52(17) . . ?
O4 C5 H5A 109.5 . . ?
O4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -27.9(3) . . . . ?
O2 C1 C2 C3 154.17(17) . . . . ?
C1 C2 C3 C4 -68.1(2) . . . . ?
C5 O4 C4 O3 4.5(3) . . . . ?
C5 O4 C4 C3 -175.16(17) . . . . ?
C2 C3 C4 O3 9.5(3) . . . . ?
C2 C3 C4 O4 -170.88(16) . . . . ?

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
_geom_hbond_publ_flag
O2 H1 O1 0.87(3) 1.80(3) 2.657(2) 173(3) 3 yes
C2 H2A O4 0.99 2.49 3.407(3) 153.8 1_545 yes
C3 H3A O2 0.99 2.64 3.387(3) 132.0 1_565 yes
C3 H3B O3 0.99 2.46 3.279(3) 140.2 4_566 yes

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.068

_shelx_res_file                  
;
TITL PL_SAE07b in P2(1)/c
    PL_SAE07b.res
    created by SHELXL-2018/1 at 15:16:52 on 12-Apr-2018
CELL 1.54178  11.31260   5.58690   9.68910  90.0000  92.8659  90.0000
ZERR 4.00000 0.00050 0.00030 0.00040 0.0000 0.0024 0.0000
LATT  1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H O
UNIT 20 32 16
LIST 4
TEMP -100.150
SIZE 0.029 0.097 0.256
ACTA
CONF
L.S. 4
BOND $H
HTAB
EQIV $1 -x, -y, -z
HTAB O2 O1_$1
EQIV $2 x, y-1, z
HTAB C2 O4_$2
EQIV $3 x, y+1, z
HTAB C3 O2_$3
EQIV $4 x, -y+1/2, z+1/2
HTAB C3 O3_$4
FMAP 2
PLAN 10
WGHT    0.036300    0.474900
FVAR       0.40782
O1    3    0.043260    0.232230    0.097625    11.00000    0.02963    0.01980 =
         0.02794    0.00093   -0.00727    0.00217
H1    2    0.054393   -0.164052    0.048947    11.00000   -1.20000
O2    3    0.105870   -0.146175    0.117225    11.00000    0.03652    0.01839 =
         0.02809   -0.00163   -0.00981    0.00132
O3    3    0.331895    0.318990    0.095723    11.00000    0.04033    0.02878 =
         0.02632   -0.01008    0.00905   -0.00802
O4    3    0.359542    0.658726    0.215833    11.00000    0.02513    0.01876 =
         0.02979   -0.00463    0.00270   -0.00124
C1    1    0.103707    0.079195    0.157410    11.00000    0.02034    0.01624 =
         0.02022    0.00279    0.00440   -0.00115
C2    1    0.179412    0.127127    0.286451    11.00000    0.02603    0.02050 =
         0.01850    0.00122   -0.00075    0.00059
AFIX  23
H2A   2    0.249002    0.019546    0.287910    11.00000   -1.20000
H2B   2    0.133462    0.088211    0.367825    11.00000   -1.20000
AFIX   0
C3    1    0.222225    0.384508    0.298762    11.00000    0.02530    0.02057 =
         0.01754   -0.00229   -0.00076    0.00263
AFIX  23
H3A   2    0.153475    0.493753    0.288059    11.00000   -1.20000
H3B   2    0.260005    0.410079    0.391973    11.00000   -1.20000
AFIX   0
C4    1    0.309117    0.444102    0.191966    11.00000    0.02162    0.01979 =
         0.01857   -0.00232   -0.00377    0.00150
C5    1    0.437649    0.740907    0.111908    11.00000    0.03275    0.02683 =
         0.03826   -0.00204    0.00719   -0.00591
AFIX 137
H5A   2    0.460653    0.907140    0.131222    11.00000   -1.50000
H5B   2    0.396656    0.731337    0.020551    11.00000   -1.50000
H5C   2    0.508530    0.639896    0.113578    11.00000   -1.50000
AFIX   0
HKLF 4




REM  PL_SAE07b in P2(1)/c
REM R1 =  0.0524 for    1085 Fo > 4sig(Fo)  and  0.0598 for all    1191 data
REM     86 parameters refined using      0 restraints

END

WGHT      0.0363      0.4749

REM Instructions for potential hydrogen bonds
HTAB O2 O1_$1
HTAB C2 O4_$2
HTAB C3 O2_$3
HTAB C3 O3_$4

REM Highest difference peak  0.244,  deepest hole -0.358,  1-sigma level  0.068
Q1    1   0.2635  0.4172  0.2401  11.00000  0.05    0.24
Q2    1   0.1139  0.1196  0.3278  11.00000  0.05    0.22
Q3    1   0.3619  0.6726  0.3663  11.00000  0.05    0.19
Q4    1   0.0033  0.2468  0.2227  11.00000  0.05    0.19
Q5    1   0.4569  0.8616  0.1692  11.00000  0.05    0.18
Q6    1  -0.0580  0.1337  0.1606  11.00000  0.05    0.18
Q7    1   0.1995  0.2643  0.2885  11.00000  0.05    0.18
Q8    1  -0.0526  0.2040  0.1805  11.00000  0.05    0.17
Q9    1  -0.0749  0.2136  0.0949  11.00000  0.05    0.17
Q10   1   0.5199  0.7436 -0.0266  11.00000  0.05    0.16
;
_shelx_res_checksum              44645

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
