# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2075520'
loop_
_audit_author_name
_audit_author_address
'Evgeniy Losev'
;Boreskov Institute of Catalysis SB RAS
Russia
;
_audit_update_record             
;
2021-04-06 deposited with the CCDC.	2021-07-29 downloaded from the CCDC.
;
_audit_creation_date             2021-04-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'GABA-L-tartaric acid (1:1) monohydrate'
_chemical_name_systematic        'GABA-L-tartaric acid (1:1) monohydrate'
_chemical_formula_moiety         'C4 H5 O6, C4 H10 N O2, H2 O'
_chemical_formula_sum            'C8 H17 N O9'
_chemical_formula_weight         271.22
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H15 N1 O8'
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'
N N 0.0061 0.0033 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.1846(2)
_cell_length_b                   27.8403(8)
_cell_length_c                   7.4558(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.007(3)
_cell_angle_gamma                90
_cell_volume                     1213.76(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4355
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.0560
_cell_measurement_theta_min      2.9090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'antisolvent crystallization'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.463
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   75.00  110.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0467  178.0000 -150.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega   64.00  100.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0467  178.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -39.00   52.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0467  -19.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega  -83.00  -53.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -       23.0467 -178.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  5 omega  -69.00   45.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.5155   77.0000  -60.0000 114

#__ type_ start__ end____ width___ exp.time_
  6 omega -109.00   15.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.5155  -57.0000  -30.0000 124

#__ type_ start__ end____ width___ exp.time_
  7 omega -116.00   16.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.5155  -57.0000   90.0000 132

#__ type_ start__ end____ width___ exp.time_
  8 omega -122.00   11.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.5155  -57.0000 -150.0000 133

#__ type_ start__ end____ width___ exp.time_
  9 omega  -80.00    1.00   1.0000  135.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.5155   37.0000  -90.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0323016000
_diffrn_orient_matrix_UB_12      -0.0210651000
_diffrn_orient_matrix_UB_13      0.0558461000
_diffrn_orient_matrix_UB_21      0.0770017000
_diffrn_orient_matrix_UB_22      0.0136929000
_diffrn_orient_matrix_UB_23      0.0736269000
_diffrn_orient_matrix_UB_31      -0.0879611000
_diffrn_orient_matrix_UB_32      0.0042411000
_diffrn_orient_matrix_UB_33      0.0398037000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4034
_reflns_number_total             4952
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.484
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4952
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+0.2652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B), O2(H2A,H2B)
2.b Ternary CH refined with riding coordinates:
 C13(H13A), C12(H12D), C23(H23), C22(H22)
2.c Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C27(H27A,H27B), C16(H16A,H16B), C17(H17A,H17B), C28(H28A,
 H28B), C26(H26A,H26B)
2.d Idealised Me refined as rotating group:
 N11(H11A,H11B,H11C), N12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O12(H12), O13(H13), O14(H14), O21(H21), O24(H24), O27(H27), O17(H17), O23(H23A)
;
_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
O11 O 1.0785(5) 0.58884(11) 0.1933(4) 0.0344(7) Uani 1 1 d . . . . .
O12 O 0.8139(5) 0.53524(11) 0.0472(4) 0.0366(7) Uani 1 1 d . . . . .
H12 H 0.835992 0.546140 -0.047558 0.055 Uiso 1 1 calc GR . . . .
O13 O 0.7927(5) 0.49948(10) 0.3745(4) 0.0339(6) Uani 1 1 d . . . . .
H13 H 0.658763 0.501615 0.306720 0.051 Uiso 1 1 calc GR . . . .
O16 O 0.8911(5) 0.56621(12) 0.7579(4) 0.0407(7) Uani 1 1 d . . . . .
O14 O 0.5575(4) 0.59045(11) 0.2804(4) 0.0354(7) Uani 1 1 d . . . . .
H14 H 0.450972 0.585120 0.320303 0.053 Uiso 1 1 calc GR . . . .
O15 O 0.5187(5) 0.57727(12) 0.6105(4) 0.0417(8) Uani 1 1 d . . . . .
O26 O 0.3365(5) 0.47297(13) 0.2496(4) 0.0473(8) Uani 1 1 d . . . . .
O21 O 0.3335(6) 0.47151(12) -0.3981(4) 0.0485(8) Uani 1 1 d . . . . .
H21 H 0.344214 0.468801 -0.504384 0.073 Uiso 1 1 calc GR . . . .
O24 O 0.0578(5) 0.41511(13) -0.1902(4) 0.0468(9) Uani 1 1 d . . . . .
H24 H -0.013707 0.402100 -0.128350 0.070 Uiso 1 1 calc GR . . . .
N11 N 0.3342(5) 0.60225(13) 0.8867(5) 0.0344(9) Uani 1 1 d . . . . .
H11A H 0.412133 0.591571 0.813272 0.041 Uiso 1 1 calc GR . . . .
H11B H 0.193888 0.589892 0.847379 0.041 Uiso 1 1 calc GR . . . .
H11C H 0.405295 0.593394 1.006163 0.041 Uiso 1 1 calc GR . . . .
O25 O 0.0585(5) 0.41892(12) 0.1531(4) 0.0452(8) Uani 1 1 d . . . . .
C11 C 0.9422(6) 0.55773(14) 0.1966(5) 0.0244(8) Uani 1 1 d . . . . .
O22 O 0.5313(6) 0.40370(14) -0.3462(5) 0.0585(10) Uani 1 1 d . . . . .
N12 N -0.1632(6) 0.39763(12) 0.4148(5) 0.0346(8) Uani 1 1 d . . . . .
H12A H -0.083430 0.409499 0.344816 0.041 Uiso 1 1 calc GR . . . .
H12B H -0.098301 0.406499 0.535058 0.041 Uiso 1 1 calc GR . . . .
H12C H -0.305708 0.408792 0.371951 0.041 Uiso 1 1 calc GR . . . .
O27 O 0.3157(6) 0.20293(12) 0.4872(6) 0.0645(10) Uani 1 1 d . . . . .
H27 H 0.449046 0.193924 0.517931 0.097 Uiso 1 1 calc GR . . . .
C14 C 0.7192(7) 0.57545(14) 0.6146(5) 0.0279(9) Uani 1 1 d . . . . .
C24 C 0.2016(7) 0.44712(14) 0.1271(5) 0.0282(9) Uani 1 1 d . . . . .
O28 O 0.4773(7) 0.27116(15) 0.6089(7) 0.0842(14) Uani 1 1 d . . . . .
C13 C 0.7666(6) 0.58490(14) 0.4293(5) 0.0251(8) Uani 1 1 d . . . . .
H13A H 0.855182 0.614633 0.442020 0.030 Uiso 1 1 calc R . . . .
O17 O 0.7811(7) 0.80009(14) 0.9714(7) 0.0748(12) Uani 1 1 d . . . . .
H17 H 0.912529 0.810189 1.013632 0.112 Uiso 1 1 calc GR . . . .
C12 C 0.9013(6) 0.54391(14) 0.3806(5) 0.0240(8) Uani 1 1 d . . . . .
H12D H 1.050355 0.542262 0.480579 0.029 Uiso 1 1 calc R . . . .
O18 O 0.9502(7) 0.73256(15) 1.0922(7) 0.0850(14) Uani 1 1 d . . . . .
C21 C 0.4414(7) 0.43636(16) -0.2918(6) 0.0312(10) Uani 1 1 d . . . . .
C18 C 0.3200(7) 0.65511(17) 0.8757(7) 0.0417(11) Uani 1 1 d . . . . .
H18A H 0.227539 0.666559 0.949865 0.050 Uiso 1 1 calc R . . . .
H18B H 0.245894 0.664725 0.744934 0.050 Uiso 1 1 calc R . . . .
C23 C 0.2059(6) 0.44980(14) -0.0775(5) 0.0274(8) Uani 1 1 d . . . . .
H23 H 0.156921 0.481843 -0.129310 0.033 Uiso 1 1 calc R . . A .
C27 C 0.0710(8) 0.32415(17) 0.4730(7) 0.0418(11) Uani 1 1 d . . . . .
H27A H 0.139243 0.331880 0.606405 0.050 Uiso 1 1 calc R . . . .
H27B H 0.162667 0.339209 0.405025 0.050 Uiso 1 1 calc R . . . .
C16 C 0.5459(9) 0.73150(18) 0.9301(7) 0.0497(12) Uani 1 1 d . . . . .
H16A H 0.448416 0.744323 0.997523 0.060 Uiso 1 1 calc R . . . .
H16B H 0.478545 0.739971 0.797340 0.060 Uiso 1 1 calc R . . . .
C17 C 0.5543(8) 0.67777(18) 0.9488(7) 0.0460(12) Uani 1 1 d . . . . .
H17A H 0.624999 0.669297 1.081271 0.055 Uiso 1 1 calc R . . . .
H17B H 0.648920 0.664891 0.878925 0.055 Uiso 1 1 calc R . . . .
C25 C 0.3099(9) 0.24886(17) 0.5248(7) 0.0461(12) Uani 1 1 d . . . . .
C22 C 0.4418(7) 0.43949(17) -0.0874(6) 0.0357(10) Uani 1 1 d . . . B 1
H22 H 0.545312 0.465373 -0.022739 0.043 Uiso 1 1 calc R . . B 1
C28 C -0.1668(7) 0.34427(15) 0.4021(6) 0.0374(10) Uani 1 1 d . . . . .
H28A H -0.239884 0.334608 0.271305 0.045 Uiso 1 1 calc R . . . .
H28B H -0.255563 0.331366 0.476920 0.045 Uiso 1 1 calc R . . . .
C15 C 0.7786(10) 0.75419(18) 1.0071(7) 0.0503(13) Uani 1 1 d . . . . .
C26 C 0.0753(8) 0.27005(16) 0.4478(7) 0.0430(11) Uani 1 1 d . . . . .
H26A H -0.022196 0.255211 0.510975 0.052 Uiso 1 1 calc R . . . .
H26B H 0.012357 0.262540 0.313730 0.052 Uiso 1 1 calc R . . . .
O1 O 0.2468(6) 0.67600(12) 0.3839(6) 0.0583(10) Uani 1 1 d . . . . .
H1A H 0.152870 0.694685 0.306659 0.087 Uiso 1 1 d G . . . .
H1B H 0.216121 0.647105 0.347879 0.087 Uiso 1 1 d G . . . .
O2 O 0.7891(6) 0.32405(14) 0.9044(6) 0.0662(11) Uani 1 1 d . . . . .
H2A H 0.723343 0.305255 0.812938 0.099 Uiso 1 1 d G . . . .
H2B H 0.708291 0.349055 0.897037 0.099 Uiso 1 1 d G . . . .
O23 O 0.5200(6) 0.39544(15) 0.0103(5) 0.0688(12) Uani 1 1 d . . . B 1
H23A H 0.659408 0.396313 0.059161 0.103 Uiso 1 1 calc GR . . B 1


_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
O11 C11 1.214(5) . ?
O12 H12 0.8200 . ?
O12 C11 1.299(4) . ?
O13 H13 0.8200 . ?
O13 C12 1.401(5) . ?
O16 C14 1.264(5) . ?
O14 H14 0.8200 . ?
O14 C13 1.412(4) . ?
O15 C14 1.232(5) . ?
O26 C24 1.246(5) . ?
O21 H21 0.8200 . ?
O21 C21 1.299(5) . ?
O24 H24 0.8200 . ?
O24 C23 1.405(5) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
N11 H11C 0.8900 . ?
N11 C18 1.475(6) . ?
O25 C24 1.245(5) . ?
C11 C12 1.524(5) . ?
O22 C21 1.203(5) . ?
N12 H12A 0.8900 . ?
N12 H12B 0.8900 . ?
N12 H12C 0.8900 . ?
N12 C28 1.488(5) . ?
O27 H27 0.8200 . ?
O27 C25 1.312(6) . ?
C14 C13 1.526(5) . ?
C24 C23 1.536(5) . ?
O28 C25 1.195(6) . ?
C13 H13A 0.9800 . ?
C13 C12 1.525(5) . ?
O17 H17 0.8200 . ?
O17 C15 1.306(6) . ?
C12 H12D 0.9800 . ?
O18 C15 1.206(6) . ?
C21 C22 1.525(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.510(6) . ?
C23 H23 0.9800 . ?
C23 C22 1.513(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.500(6) . ?
C27 C26 1.519(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.502(7) . ?
C16 C15 1.503(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C25 C26 1.497(7) . ?
C22 H22 0.9800 . ?
C22 O23 1.428(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
O1 H1A 0.8495 . ?
O1 H1B 0.8495 . ?
O2 H2A 0.8504 . ?
O2 H2B 0.8485 . ?
O23 H23A 0.8200 . ?

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
C11 O12 H12 109.5 . . ?
C12 O13 H13 109.5 . . ?
C13 O14 H14 109.5 . . ?
C21 O21 H21 109.5 . . ?
C23 O24 H24 109.5 . . ?
H11A N11 H11B 109.5 . . ?
H11A N11 H11C 109.5 . . ?
H11B N11 H11C 109.5 . . ?
C18 N11 H11A 109.5 . . ?
C18 N11 H11B 109.5 . . ?
C18 N11 H11C 109.5 . . ?
O11 C11 O12 124.1(3) . . ?
O11 C11 C12 121.2(3) . . ?
O12 C11 C12 114.6(3) . . ?
H12A N12 H12B 109.5 . . ?
H12A N12 H12C 109.5 . . ?
H12B N12 H12C 109.5 . . ?
C28 N12 H12A 109.5 . . ?
C28 N12 H12B 109.5 . . ?
C28 N12 H12C 109.5 . . ?
C25 O27 H27 109.5 . . ?
O16 C14 C13 116.3(3) . . ?
O15 C14 O16 126.3(4) . . ?
O15 C14 C13 117.3(3) . . ?
O26 C24 C23 118.4(3) . . ?
O25 C24 O26 126.2(4) . . ?
O25 C24 C23 115.4(3) . . ?
O14 C13 C14 109.5(3) . . ?
O14 C13 H13A 108.9 . . ?
O14 C13 C12 109.0(3) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 C14 111.5(3) . . ?
C12 C13 H13A 108.9 . . ?
C15 O17 H17 109.5 . . ?
O13 C12 C11 114.3(3) . . ?
O13 C12 C13 112.1(3) . . ?
O13 C12 H12D 107.8 . . ?
C11 C12 C13 106.8(3) . . ?
C11 C12 H12D 107.8 . . ?
C13 C12 H12D 107.8 . . ?
O21 C21 C22 113.6(4) . . ?
O22 C21 O21 124.4(4) . . ?
O22 C21 C22 122.0(4) . . ?
N11 C18 H18A 109.4 . . ?
N11 C18 H18B 109.4 . . ?
N11 C18 C17 111.3(4) . . ?
H18A C18 H18B 108.0 . . ?
C17 C18 H18A 109.4 . . ?
C17 C18 H18B 109.4 . . ?
O24 C23 C24 110.0(3) . . ?
O24 C23 H23 109.4 . . ?
O24 C23 C22 106.9(3) . . ?
C24 C23 H23 109.4 . . ?
C22 C23 C24 111.6(3) . . ?
C22 C23 H23 109.4 . . ?
H27A C27 H27B 107.9 . . ?
C28 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
C28 C27 C26 112.4(4) . . ?
C26 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C17 C16 C15 112.5(4) . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C16 C17 C18 112.5(4) . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
O27 C25 C26 113.1(4) . . ?
O28 C25 O27 122.6(5) . . ?
O28 C25 C26 124.2(5) . . ?
C21 C22 H22 108.8 . . ?
C23 C22 C21 111.8(3) . . ?
C23 C22 H22 108.8 . . ?
O23 C22 C21 110.6(4) . . ?
O23 C22 C23 108.0(3) . . ?
O23 C22 H22 108.8 . . ?
N12 C28 C27 111.0(3) . . ?
N12 C28 H28A 109.4 . . ?
N12 C28 H28B 109.4 . . ?
C27 C28 H28A 109.4 . . ?
C27 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
O17 C15 C16 114.0(5) . . ?
O18 C15 O17 121.9(5) . . ?
O18 C15 C16 124.1(5) . . ?
C27 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C25 C26 C27 113.4(4) . . ?
C25 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
H1A O1 H1B 109.4 . . ?
H2A O2 H2B 109.6 . . ?
C22 O23 H23A 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
_geom_hbond_publ_flag
O12 H12 O16 0.82 1.69 2.509(4) 177.0 1_554 yes
O13 H13 O26 0.82 2.06 2.768(4) 144.6 . yes
O14 H14 O11 0.82 2.19 2.819(4) 133.7 1_455 yes
O21 H21 O26 0.82 1.82 2.633(4) 169.4 1_554 yes
N11 H11A O15 0.89 1.88 2.749(4) 165.5 . yes
N11 H11B O16 0.89 1.89 2.779(4) 177.5 1_455 yes
N11 H11C O14 0.89 1.95 2.827(4) 166.2 1_556 yes
N12 H12A O25 0.89 1.92 2.789(4) 163.8 . yes
N12 H12B O24 0.89 1.97 2.856(4) 170.8 1_556 yes
O27 H27 O1 0.82 1.85 2.667(5) 173.2 2_646 yes
O17 H17 O2 0.82 1.79 2.601(6) 171.7 2_757 yes
O1 H1A O18 0.85 1.98 2.824(6) 170.1 1_454 yes
O1 H1B O11 0.85 2.01 2.833(4) 162.5 1_455 yes
O2 H2A O28 0.85 2.01 2.824(6) 161.0 . yes
O2 H2B O22 0.85 2.35 3.002(5) 134.3 1_556 yes
O2 H2B O23 0.85 2.09 2.864(5) 150.9 1_556 yes
O23 H23A N12 0.82 2.52 3.014(5) 120.2 1_655 yes

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
O11 C11 C12 O13 -162.7(4) . . . . ?
O11 C11 C12 C13 72.8(4) . . . . ?
O12 C11 C12 O13 20.2(5) . . . . ?
O12 C11 C12 C13 -104.4(4) . . . . ?
O16 C14 C13 O14 174.9(3) . . . . ?
O16 C14 C13 C12 54.1(4) . . . . ?
O14 C13 C12 O13 -65.9(4) . . . . ?
O14 C13 C12 C11 60.1(4) . . . . ?
O15 C14 C13 O14 -4.7(5) . . . . ?
O15 C14 C13 C12 -125.5(4) . . . . ?
O26 C24 C23 O24 174.6(4) . . . . ?
O26 C24 C23 C22 56.1(5) . . . . ?
O21 C21 C22 C23 47.6(5) . . . . ?
O21 C21 C22 O23 168.0(4) . . . . ?
O24 C23 C22 C21 53.1(4) . . . . ?
O24 C23 C22 O23 -68.8(4) . . . . ?
N11 C18 C17 C16 177.1(4) . . . . ?
O25 C24 C23 O24 -6.1(5) . . . . ?
O25 C24 C23 C22 -124.6(4) . . . . ?
O22 C21 C22 C23 -131.5(4) . . . . ?
O22 C21 C22 O23 -11.1(6) . . . . ?
O27 C25 C26 C27 -174.0(4) . . . . ?
C14 C13 C12 O13 55.2(4) . . . . ?
C14 C13 C12 C11 -178.9(3) . . . . ?
C24 C23 C22 C21 173.4(3) . . . . ?
C24 C23 C22 O23 51.5(4) . . . . ?
O28 C25 C26 C27 4.5(8) . . . . ?
C17 C16 C15 O17 171.7(5) . . . . ?
C17 C16 C15 O18 -7.3(8) . . . . ?
C28 C27 C26 C25 -177.6(4) . . . . ?
C15 C16 C17 C18 178.7(4) . . . . ?
C26 C27 C28 N12 -175.5(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTiGen microloop, cryo-oil'
_olex2_submission_special_instructions 'No special instructions were received'
