# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_mhmg1_2
_database_code_depnum_ccdc_archive 'CCDC 1890935'
loop_
_audit_author_name
_audit_author_address
'Wilhelm Maximilian Hutzler'
;UCLouvain
Belgium
;
_audit_update_record             
;
2019-01-15 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Ectoine
_chemical_name_common            
'(S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 N2 O2'
_chemical_formula_sum            'C6 H10 N2 O2'
_chemical_formula_weight         142.16

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'
N N 0.0311 0.0180 '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           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                   5.21733(4)
_cell_length_b                   9.11328(7)
_cell_length_c                   14.35413(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.7911(3)
_cell_angle_gamma                90
_cell_volume                     682.431(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7743
_cell_measurement_theta_min      3.079
_cell_measurement_theta_max      59.935

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.879
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_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  'Siemens CCD three-circle diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10356
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.079
_diffrn_reflns_theta_max         69.929
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.882
_reflns_number_total             2230
_reflns_number_gt                2229
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_max     0.757
_reflns_Friedel_fraction_full    0.780

_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       'APEX3 (Bruker, 2012)'
_computing_cell_refinement       'APEX3 (Bruker, 2012)'
_computing_data_reduction        'APEX3 (Bruker, 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    
;
Mercury (Version 3.3, Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick,
2008)
;

_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0644P)²+0.2633P] 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 907 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.06(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2230
_refine_ls_number_parameters     195
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_restrained_S_all      1.169
_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
N1A N 0.1686(5) 0.7849(3) 0.43193(17) 0.0241(6) Uani 1 1 d D . . . .
H1A H 0.110(6) 0.790(4) 0.4903(18) 0.029 Uiso 1 1 d D U . . .
C2A C 0.3498(5) 0.6908(3) 0.41216(19) 0.0215(6) Uani 1 1 d . . . . .
C21A C 0.4658(6) 0.5990(4) 0.4882(2) 0.0319(8) Uani 1 1 d . . . . .
H21A H 0.4193 0.6398 0.5489 0.048 Uiso 1 1 calc R U . . .
H21B H 0.6528 0.5988 0.4826 0.048 Uiso 1 1 calc R U . . .
H21C H 0.4013 0.4983 0.4831 0.048 Uiso 1 1 calc R U . . .
N3A N 0.4337(5) 0.6737(3) 0.32616(16) 0.0201(5) Uani 1 1 d D . . . .
H3A H 0.565(5) 0.620(4) 0.318(2) 0.024 Uiso 1 1 d D U . . .
C4A C 0.3137(5) 0.7500(3) 0.24697(18) 0.0191(6) Uani 1 1 d . . . . .
H4A H 0.1577 0.6934 0.2276 0.023 Uiso 1 1 calc R U . . .
C41A C 0.4963(6) 0.7538(3) 0.1640(2) 0.0225(6) Uani 1 1 d . . . . .
O41A O 0.6760(5) 0.6663(3) 0.16333(18) 0.0493(8) Uani 1 1 d . . . . .
O42A O 0.4389(5) 0.8446(3) 0.10141(15) 0.0346(6) Uani 1 1 d . . . . .
C5A C 0.2271(6) 0.9004(3) 0.2798(2) 0.0251(7) Uani 1 1 d . . . . .
H5A1 H 0.1348 0.9515 0.2286 0.030 Uiso 1 1 calc R U . . .
H5A2 H 0.3783 0.9602 0.2978 0.030 Uiso 1 1 calc R U . . .
C6A C 0.0504(6) 0.8828(4) 0.3633(2) 0.0274(7) Uani 1 1 d . . . . .
H6A1 H 0.0190 0.9799 0.3920 0.033 Uiso 1 1 calc R U . . .
H6A2 H -0.1164 0.8420 0.3423 0.033 Uiso 1 1 calc R U . . .
N1B N 1.3198(5) 0.3307(3) 0.06380(17) 0.0218(6) Uani 1 1 d D . . . .
H1B H 1.396(6) 0.334(4) 0.0096(18) 0.026 Uiso 1 1 d D U . . .
C2B C 1.1307(5) 0.4208(3) 0.08167(18) 0.0189(6) Uani 1 1 d . . . . .
C21B C 1.0449(6) 0.5261(4) 0.0084(2) 0.0286(8) Uani 1 1 d . . . . .
H21D H 0.9125 0.4801 -0.0309 0.043 Uiso 1 1 calc R U . . .
H21E H 1.1911 0.5535 -0.0301 0.043 Uiso 1 1 calc R U . . .
H21F H 0.9745 0.6141 0.0378 0.043 Uiso 1 1 calc R U . . .
N3B N 1.0117(5) 0.4186(3) 0.16242(16) 0.0192(5) Uani 1 1 d D . . . .
H3B H 0.899(6) 0.483(4) 0.181(2) 0.023 Uiso 1 1 d D U . . .
C4B C 1.0813(5) 0.3143(3) 0.23602(19) 0.0188(6) Uani 1 1 d . . . . .
H4B H 0.9922 0.2195 0.2222 0.023 Uiso 1 1 calc R U . . .
C41B C 0.9945(5) 0.3673(3) 0.3322(2) 0.0211(6) Uani 1 1 d . . . . .
O41B O 0.8855(4) 0.4873(3) 0.33763(14) 0.0281(5) Uani 1 1 d . . . . .
O42B O 1.0452(5) 0.2781(3) 0.39672(15) 0.0366(6) Uani 1 1 d . . . . .
C5B C 1.3702(5) 0.2874(3) 0.23084(19) 0.0200(6) Uani 1 1 d . . . . .
H5B1 H 1.4642 0.3795 0.2444 0.024 Uiso 1 1 calc R U . . .
H5B2 H 1.4228 0.2131 0.2776 0.024 Uiso 1 1 calc R U . . .
C6B C 1.4337(5) 0.2337(3) 0.1338(2) 0.0217(6) Uani 1 1 d . . . . .
H6B1 H 1.6220 0.2312 0.1263 0.026 Uiso 1 1 calc R U . . .
H6B2 H 1.3671 0.1329 0.1250 0.026 Uiso 1 1 calc R U . . .


_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
N1A C2A 1.310(4) . ?
N1A C6A 1.459(4) . ?
N1A H1A 0.90(2) . ?
C2A N3A 1.325(4) . ?
C2A C21A 1.497(4) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
N3A C4A 1.466(4) . ?
N3A H3A 0.85(2) . ?
C4A C5A 1.519(4) . ?
C4A C41A 1.535(4) . ?
C4A H4A 1.0000 . ?
C41A O41A 1.231(4) . ?
C41A O42A 1.255(4) . ?
C5A C6A 1.531(4) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
N1B C2B 1.312(4) . ?
N1B C6B 1.458(4) . ?
N1B H1B 0.88(2) . ?
C2B N3B 1.323(4) . ?
C2B C21B 1.488(4) . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
N3B C4B 1.463(4) . ?
N3B H3B 0.87(2) . ?
C4B C5B 1.530(4) . ?
C4B C41B 1.537(4) . ?
C4B H4B 1.0000 . ?
C41B O41B 1.236(4) . ?
C41B O42B 1.258(4) . ?
C5B C6B 1.518(4) . ?
C5B H5B1 0.9900 . ?
C5B H5B2 0.9900 . ?
C6B H6B1 0.9900 . ?
C6B H6B2 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
C2A N1A C6A 123.6(2) . . ?
C2A N1A H1A 120(2) . . ?
C6A N1A H1A 117(2) . . ?
N1A C2A N3A 121.8(3) . . ?
N1A C2A C21A 119.6(3) . . ?
N3A C2A C21A 118.6(3) . . ?
C2A C21A H21A 109.5 . . ?
C2A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C2A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C2A N3A C4A 121.6(2) . . ?
C2A N3A H3A 118(2) . . ?
C4A N3A H3A 120(2) . . ?
N3A C4A C5A 108.3(2) . . ?
N3A C4A C41A 110.4(2) . . ?
C5A C4A C41A 114.2(2) . . ?
N3A C4A H4A 107.9 . . ?
C5A C4A H4A 107.9 . . ?
C41A C4A H4A 107.9 . . ?
O41A C41A O42A 126.5(3) . . ?
O41A C41A C4A 118.2(3) . . ?
O42A C41A C4A 115.2(2) . . ?
C4A C5A C6A 109.5(2) . . ?
C4A C5A H5A1 109.8 . . ?
C6A C5A H5A1 109.8 . . ?
C4A C5A H5A2 109.8 . . ?
C6A C5A H5A2 109.8 . . ?
H5A1 C5A H5A2 108.2 . . ?
N1A C6A C5A 109.8(2) . . ?
N1A C6A H6A1 109.7 . . ?
C5A C6A H6A1 109.7 . . ?
N1A C6A H6A2 109.7 . . ?
C5A C6A H6A2 109.7 . . ?
H6A1 C6A H6A2 108.2 . . ?
C2B N1B C6B 123.0(2) . . ?
C2B N1B H1B 120(2) . . ?
C6B N1B H1B 117(2) . . ?
N1B C2B N3B 121.7(3) . . ?
N1B C2B C21B 119.0(2) . . ?
N3B C2B C21B 119.3(3) . . ?
C2B C21B H21D 109.5 . . ?
C2B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C2B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C2B N3B C4B 121.8(2) . . ?
C2B N3B H3B 126(2) . . ?
C4B N3B H3B 112(2) . . ?
N3B C4B C5B 107.7(2) . . ?
N3B C4B C41B 111.8(2) . . ?
C5B C4B C41B 113.4(2) . . ?
N3B C4B H4B 107.9 . . ?
C5B C4B H4B 107.9 . . ?
C41B C4B H4B 107.9 . . ?
O41B C41B O42B 128.2(3) . . ?
O41B C41B C4B 118.5(3) . . ?
O42B C41B C4B 113.4(3) . . ?
C6B C5B C4B 108.9(2) . . ?
C6B C5B H5B1 109.9 . . ?
C4B C5B H5B1 109.9 . . ?
C6B C5B H5B2 109.9 . . ?
C4B C5B H5B2 109.9 . . ?
H5B1 C5B H5B2 108.3 . . ?
N1B C6B C5B 110.2(2) . . ?
N1B C6B H6B1 109.6 . . ?
C5B C6B H6B1 109.6 . . ?
N1B C6B H6B2 109.6 . . ?
C5B C6B H6B2 109.6 . . ?
H6B1 C6B H6B2 108.1 . . ?

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
C6A N1A C2A N3A -2.6(5) . . . . ?
C6A N1A C2A C21A 177.7(3) . . . . ?
N1A C2A N3A C4A -5.3(4) . . . . ?
C21A C2A N3A C4A 174.5(3) . . . . ?
C2A N3A C4A C5A 35.0(4) . . . . ?
C2A N3A C4A C41A 160.8(3) . . . . ?
N3A C4A C41A O41A 18.4(4) . . . . ?
C5A C4A C41A O41A 140.7(3) . . . . ?
N3A C4A C41A O42A -164.0(3) . . . . ?
C5A C4A C41A O42A -41.7(4) . . . . ?
N3A C4A C5A C6A -55.6(3) . . . . ?
C41A C4A C5A C6A -179.0(3) . . . . ?
C2A N1A C6A C5A -20.7(4) . . . . ?
C4A C5A C6A N1A 49.1(4) . . . . ?
C6B N1B C2B N3B -7.4(4) . . . . ?
C6B N1B C2B C21B 173.9(3) . . . . ?
N1B C2B N3B C4B -0.9(4) . . . . ?
C21B C2B N3B C4B 177.9(3) . . . . ?
C2B N3B C4B C5B 33.4(3) . . . . ?
C2B N3B C4B C41B 158.6(3) . . . . ?
N3B C4B C41B O41B -1.4(4) . . . . ?
C5B C4B C41B O41B 120.6(3) . . . . ?
N3B C4B C41B O42B 178.1(2) . . . . ?
C5B C4B C41B O42B -59.9(3) . . . . ?
N3B C4B C5B C6B -56.6(3) . . . . ?
C41B C4B C5B C6B 179.2(2) . . . . ?
C2B N1B C6B C5B -19.1(4) . . . . ?
C4B C5B C6B N1B 50.3(3) . . . . ?

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
N1A H1A O42B 0.90(2) 1.83(2) 2.715(3) 171(4) 2_656
N3A H3A O41B 0.85(2) 2.08(2) 2.908(3) 164(3) .
N1B H1B O42A 0.88(2) 1.83(2) 2.703(3) 178(4) 2_745
N3B H3B O41A 0.87(2) 2.05(3) 2.857(4) 153(3) .

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.111


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: N,N-dimethylformamide (DMF)'
_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_mhmg1
_database_code_depnum_ccdc_archive 'CCDC 1890936'
loop_
_audit_author_name
_audit_author_address
'Wilhelm Maximilian Hutzler'
;UCLouvain
Belgium
;
_audit_update_record             
;
2019-01-15 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Ectoine dihydrate'
_chemical_name_common            
'(S)-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C6 H14 N2 O4'
_chemical_formula_weight         178.19

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'
N N 0.0311 0.0180 '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      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                   7.5940(3)
_cell_length_b                   8.6265(5)
_cell_length_c                   13.3619(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     875.33(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2290
_cell_measurement_theta_min      5.13
_cell_measurement_theta_max      49.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.964
_shelx_estimated_absorpt_T_min   0.723
_shelx_estimated_absorpt_T_max   0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_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  'Siemens CCD three-circle diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12908
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         6.626
_diffrn_reflns_theta_max         69.553
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             1575
_reflns_number_gt                1575
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_max     0.934
_reflns_Friedel_fraction_full    0.960

_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       'APEX3 (Bruker, 2012)'
_computing_cell_refinement       'APEX3 (Bruker, 2012)'
_computing_data_reduction        'APEX3 (Bruker, 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    
;
Mercury (Version 3.3, Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick,
2008)
;

_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0330P)²+0.2764P] 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 623 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.04(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1575
_refine_ls_number_parameters     128
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.108
_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
N1A N 0.7025(2) 0.61333(19) 0.77127(12) 0.0242(4) Uani 1 1 d D . . . .
H1A H 0.692(3) 0.575(3) 0.8295(15) 0.029 Uiso 1 1 d D U . . .
C2A C 0.5725(3) 0.6915(2) 0.73158(14) 0.0228(4) Uani 1 1 d . . . . .
C21A C 0.4076(3) 0.7163(3) 0.79017(16) 0.0325(5) Uani 1 1 d . . . . .
H21A H 0.3876 0.6273 0.8343 0.049 Uiso 1 1 calc R U . . .
H22A H 0.3079 0.7273 0.7442 0.049 Uiso 1 1 calc R U . . .
H23A H 0.4191 0.8107 0.8305 0.049 Uiso 1 1 calc R U . . .
N3A N 0.5843(2) 0.75017(19) 0.64047(12) 0.0240(4) Uani 1 1 d D . . . .
H3A H 0.496(3) 0.803(3) 0.6151(17) 0.029 Uiso 1 1 d D U . . .
C4A C 0.7372(3) 0.7252(2) 0.57666(13) 0.0226(4) Uani 1 1 d . . . . .
H4A H 0.7502 0.8167 0.5313 0.027 Uiso 1 1 calc R U . . .
C41A C 0.7155(3) 0.5782(2) 0.51143(13) 0.0215(4) Uani 1 1 d . . . . .
O41A O 0.5816(2) 0.49788(18) 0.52090(12) 0.0376(4) Uani 1 1 d . . . . .
O42A O 0.84103(19) 0.55060(17) 0.45186(10) 0.0295(4) Uani 1 1 d . . . . .
C5A C 0.9004(3) 0.7156(2) 0.64360(15) 0.0254(4) Uani 1 1 d . . . . .
H51A H 1.0050 0.6901 0.6025 0.030 Uiso 1 1 calc R U . . .
H52A H 0.9211 0.8171 0.6761 0.030 Uiso 1 1 calc R U . . .
C6A C 0.8739(3) 0.5919(2) 0.72282(14) 0.0253(4) Uani 1 1 d . . . . .
H61A H 0.8792 0.4880 0.6916 0.030 Uiso 1 1 calc R U . . .
H62B H 0.9688 0.5988 0.7734 0.030 Uiso 1 1 calc R U . . .
O1W O 0.2631(2) 0.4905(2) 0.62967(15) 0.0493(5) Uani 1 1 d D . . . .
H11W H 0.355(3) 0.491(4) 0.5912(19) 0.059 Uiso 1 1 d D U . . .
H12W H 0.194(3) 0.421(3) 0.606(2) 0.059 Uiso 1 1 d D U . . .
O2W O 0.5011(3) 0.2166(2) 0.43354(12) 0.0415(4) Uani 1 1 d D . . . .
H21W H 0.537(4) 0.300(2) 0.4609(19) 0.050 Uiso 1 1 d D U . . .
H22W H 0.447(3) 0.161(3) 0.4766(17) 0.050 Uiso 1 1 d D U . . .


_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
N1A C2A 1.308(3) . ?
N1A C6A 1.465(2) . ?
N1A H1A 0.850(19) . ?
C2A N3A 1.321(3) . ?
C2A C21A 1.492(3) . ?
C21A H21A 0.9800 . ?
C21A H22A 0.9800 . ?
C21A H23A 0.9800 . ?
N3A C4A 1.456(2) . ?
N3A H3A 0.882(19) . ?
C4A C5A 1.531(3) . ?
C4A C41A 1.547(3) . ?
C4A H4A 1.0000 . ?
C41A O41A 1.237(2) . ?
C41A O42A 1.265(2) . ?
C5A C6A 1.517(3) . ?
C5A H51A 0.9900 . ?
C5A H52A 0.9900 . ?
C6A H61A 0.9900 . ?
C6A H62B 0.9900 . ?
O1W H11W 0.867(12) . ?
O1W H12W 0.861(12) . ?
O2W H21W 0.853(12) . ?
O2W H22W 0.853(12) . ?

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
C2A N1A C6A 123.80(16) . . ?
C2A N1A H1A 120.3(17) . . ?
C6A N1A H1A 115.8(17) . . ?
N1A C2A N3A 121.30(19) . . ?
N1A C2A C21A 119.64(17) . . ?
N3A C2A C21A 119.06(18) . . ?
C2A C21A H21A 109.5 . . ?
C2A C21A H22A 109.5 . . ?
H21A C21A H22A 109.5 . . ?
C2A C21A H23A 109.5 . . ?
H21A C21A H23A 109.5 . . ?
H22A C21A H23A 109.5 . . ?
C2A N3A C4A 122.48(17) . . ?
C2A N3A H3A 120.1(15) . . ?
C4A N3A H3A 117.4(15) . . ?
N3A C4A C5A 108.14(14) . . ?
N3A C4A C41A 111.48(15) . . ?
C5A C4A C41A 111.80(16) . . ?
N3A C4A H4A 108.4 . . ?
C5A C4A H4A 108.4 . . ?
C41A C4A H4A 108.4 . . ?
O41A C41A O42A 125.35(18) . . ?
O41A C41A C4A 119.28(16) . . ?
O42A C41A C4A 115.37(16) . . ?
C6A C5A C4A 109.75(16) . . ?
C6A C5A H51A 109.7 . . ?
C4A C5A H51A 109.7 . . ?
C6A C5A H52A 109.7 . . ?
C4A C5A H52A 109.7 . . ?
H51A C5A H52A 108.2 . . ?
N1A C6A C5A 109.74(16) . . ?
N1A C6A H61A 109.7 . . ?
C5A C6A H61A 109.7 . . ?
N1A C6A H62B 109.7 . . ?
C5A C6A H62B 109.7 . . ?
H61A C6A H62B 108.2 . . ?
H11W O1W H12W 105.8(18) . . ?
H21W O2W H22W 109.6(18) . . ?

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
C6A N1A C2A N3A 4.0(3) . . . . ?
C6A N1A C2A C21A -175.59(18) . . . . ?
N1A C2A N3A C4A 3.3(3) . . . . ?
C21A C2A N3A C4A -177.08(17) . . . . ?
C2A N3A C4A C5A -33.2(2) . . . . ?
C2A N3A C4A C41A 90.1(2) . . . . ?
N3A C4A C41A O41A -2.1(2) . . . . ?
C5A C4A C41A O41A 119.11(19) . . . . ?
N3A C4A C41A O42A 178.23(16) . . . . ?
C5A C4A C41A O42A -60.6(2) . . . . ?
N3A C4A C5A C6A 54.8(2) . . . . ?
C41A C4A C5A C6A -68.29(19) . . . . ?
C2A N1A C6A C5A 20.4(3) . . . . ?
C4A C5A C6A N1A -48.9(2) . . . . ?

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
N1A H1A O42A 0.850(19) 1.98(2) 2.816(2) 170(2) 2_665
N3A H3A O42A 0.882(19) 1.94(2) 2.809(2) 167(2) 4_466
O1W H11W O41A 0.867(12) 1.961(13) 2.823(2) 172(3) .
O1W H12W O2W 0.861(12) 1.956(13) 2.804(3) 168(3) 4_456
O2W H21W O41A 0.853(12) 1.915(13) 2.761(2) 171(3) .
O2W H22W O42A 0.853(12) 2.214(14) 3.022(2) 158(2) 4_456

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.032


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: deionized water'
####################################################################### 
# 
# 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_d_h_ect173_can
_database_code_depnum_ccdc_archive 'CCDC 1955570'
loop_
_audit_author_name
_audit_author_address
'Wilhelm Maximilian Huetzler'
;Institute of Condensed Matter and Nanosciences, UCLouvain
Germany
;
# publcif _publ_body_element loop end

_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;
_publcif_datablock.id            {c650af6c-a010-4b50-a28a-ad7cd092c81e}


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,4,5,6-tetrahydro-2-methyl-4-pyrimidine carboxylic acid'
_chemical_name_common            ectoine
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C6 H14 N2 O4'
_chemical_formula_weight         178.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
H H 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
N N 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'
O O 0.0000 0.0000
'Neutron Data Booklet, ILL Grenoble, France (2003) ISBN 0-9704143-7-4'

_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                   7.5940(3)
_cell_length_b                   8.6265(5)
_cell_length_c                   13.3619(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     875.33(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6083
_cell_measurement_theta_min      4.417
_cell_measurement_theta_max      62.60

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          1.000
_exptl_crystal_size_min          1.000
_exptl_absorpt_coefficient_mu    0.044
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.4339
_exptl_absorpt_correction_T_max  0.7301
_exptl_absorpt_process_details   'ILL program D19abs'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.1698
_diffrn_radiation_type           neutrons
_diffrn_source                   'neutron reactor, ILL Grenoble'
_diffrn_measurement_device_type  '4 circle diffractometer D19'
_diffrn_measurement_method       'omega scan (step width in omega 0.07deg)'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7579
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.629
_diffrn_reflns_theta_max         62.552
_diffrn_reflns_theta_full        62.500
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.929
_reflns_number_total             2971
_reflns_number_gt                2909
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_max     0.883
_reflns_Friedel_fraction_full    0.885

_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       
'ILL program Multi Detector Acquisition software'
_computing_cell_refinement       'ILL program RAFD19'
_computing_data_reduction        'ILL program RETREAT'
_computing_structure_solution    'from X-ray structure'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Mercury (Version 4.1.3, Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick,
2008)
;

_computing_publication_material  'publCIF (Westrip, 2010)'

_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+1.2382P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2971
_refine_ls_number_parameters     292
_refine_ls_number_restraints     220
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0806
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.008
_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
N1A N 0.70269(12) 0.61354(9) 0.77181(6) 0.02045(16) Uani 1 1 d . . . . .
H1A H 0.6859(4) 0.5677(4) 0.8423(2) 0.0344(5) Uani 1 1 d . . . . .
C2A C 0.57245(16) 0.69248(12) 0.73141(8) 0.01806(19) Uani 1 1 d . . . . .
C21A C 0.40846(19) 0.71812(17) 0.79030(10) 0.0266(3) Uani 1 1 d D . . . .
H21A H 0.300(3) 0.726(3) 0.7381(19) 0.052(5) Uani 0.443(4) 1 d D U P A 1
H22A H 0.423(2) 0.8245(18) 0.8346(13) 0.037(3) Uani 0.443(4) 1 d D U P A 1
H23A H 0.390(4) 0.626(2) 0.8445(15) 0.053(6) Uani 0.443(4) 1 d D U P A 1
H24A H 0.415(6) 0.665(4) 0.8635(18) 0.058(8) Uani 0.268(4) 1 d D U P A 2
H25A H 0.386(4) 0.839(3) 0.808(2) 0.050(6) Uani 0.268(4) 1 d D U P A 2
H26A H 0.297(4) 0.669(5) 0.753(3) 0.065(10) Uani 0.268(4) 1 d D U P A 2
H27A H 0.435(6) 0.786(5) 0.853(3) 0.077(12) Uani 0.289(4) 1 d D U P A 3
H28A H 0.358(5) 0.605(3) 0.815(3) 0.063(8) Uani 0.289(4) 1 d D U P A 3
H29A H 0.304(4) 0.772(4) 0.747(2) 0.059(9) Uani 0.289(4) 1 d D U P A 3
N3A N 0.58432(12) 0.75094(9) 0.64032(6) 0.01966(15) Uani 1 1 d . . . . .
H3A H 0.4804(4) 0.8116(4) 0.6107(2) 0.0357(6) Uani 1 1 d . . . . .
C4A C 0.73732(16) 0.72497(12) 0.57689(8) 0.01677(18) Uani 1 1 d . . . . .
H4A H 0.7493(5) 0.8244(3) 0.5252(2) 0.0357(6) Uani 1 1 d . . . . .
C41A C 0.71579(16) 0.57838(12) 0.51151(8) 0.01613(19) Uani 1 1 d . . . . .
O41A O 0.5812(2) 0.49836(18) 0.52038(14) 0.0306(3) Uani 1 1 d . . . . .
O42A O 0.8424(2) 0.54933(17) 0.45286(10) 0.0225(3) Uani 1 1 d . . . . .
C5A C 0.90053(16) 0.71556(14) 0.64354(9) 0.0200(2) Uani 1 1 d . . . . .
H51A H 1.0173(4) 0.6871(4) 0.5992(3) 0.0393(6) Uani 1 1 d . . . . .
H52A H 0.9205(5) 0.8285(4) 0.6792(3) 0.0406(7) Uani 1 1 d . . . . .
C6A C 0.87349(17) 0.59167(14) 0.72315(9) 0.0204(2) Uani 1 1 d . . . . .
H62A H 0.9744(5) 0.5992(5) 0.7806(2) 0.0428(7) Uani 1 1 d . . . . .
H61A H 0.8794(5) 0.4749(4) 0.6897(2) 0.0379(6) Uani 1 1 d . . . . .
O1W O 0.2637(3) 0.4910(3) 0.63016(18) 0.0404(4) Uani 1 1 d . . . . .
H11W H 0.3688(5) 0.4914(5) 0.5911(3) 0.0470(8) Uani 1 1 d . . . . .
H12W H 0.1878(6) 0.4111(5) 0.6042(3) 0.0481(8) Uani 1 1 d . . . . .
O2W O 0.5012(3) 0.21652(19) 0.43355(13) 0.0325(3) Uani 1 1 d . . . . .
H21W H 0.5309(6) 0.3141(4) 0.4655(3) 0.0447(7) Uani 1 1 d . . . . .
H22W H 0.4391(7) 0.1538(5) 0.4814(3) 0.0533(10) Uani 1 1 d . . . . .


_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
N1A H1A 1.029(3) . ?
N1A C2A 1.3166(14) . ?
N1A C6A 1.4631(16) . ?
C2A N3A 1.3205(13) . ?
C2A C21A 1.4897(18) . ?
C21A H27A 1.04(2) . ?
C21A H26A 1.07(2) . ?
C21A H21A 1.081(15) . ?
C21A H23A 1.081(16) . ?
C21A H24A 1.08(2) . ?
C21A H25A 1.08(2) . ?
C21A H29A 1.09(2) . ?
C21A H28A 1.10(2) . ?
C21A H22A 1.098(12) . ?
N3A H3A 1.026(3) . ?
N3A C4A 1.4556(14) . ?
C4A H4A 1.105(3) . ?
C4A C5A 1.5284(17) . ?
C4A C41A 1.5456(14) . ?
C41A O41A 1.2392(18) . ?
C41A O42A 1.2655(18) . ?
C5A H51A 1.094(3) . ?
C5A H52A 1.095(3) . ?
C5A C6A 1.5217(17) . ?
C6A H62A 1.087(3) . ?
C6A H61A 1.103(3) . ?
O1W H11W 0.954(4) . ?
O1W H12W 0.963(4) . ?
O2W H22W 0.961(4) . ?
O2W H21W 0.971(4) . ?

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
H1A N1A C2A 118.7(2) . . ?
H1A N1A C6A 117.8(2) . . ?
C2A N1A C6A 123.39(9) . . ?
N1A C2A N3A 121.62(10) . . ?
N1A C2A C21A 119.22(11) . . ?
N3A C2A C21A 119.16(11) . . ?
H21A C21A H23A 113(2) . . ?
H26A C21A H24A 107(3) . . ?
H26A C21A H25A 111(3) . . ?
H24A C21A H25A 103(2) . . ?
H27A C21A H29A 109(3) . . ?
H27A C21A H28A 109(3) . . ?
H29A C21A H28A 106(3) . . ?
H21A C21A H22A 111.8(16) . . ?
H23A C21A H22A 105.2(14) . . ?
H27A C21A C2A 110(3) . . ?
H26A C21A C2A 111(2) . . ?
H21A C21A C2A 107.7(16) . . ?
H23A C21A C2A 110.6(15) . . ?
H24A C21A C2A 112(2) . . ?
H25A C21A C2A 112.9(19) . . ?
H29A C21A C2A 113.2(19) . . ?
H28A C21A C2A 108.6(18) . . ?
H22A C21A C2A 108.9(9) . . ?
H3A N3A C2A 119.8(2) . . ?
H3A N3A C4A 117.9(2) . . ?
C2A N3A C4A 122.16(9) . . ?
H4A C4A N3A 108.1(2) . . ?
H4A C4A C5A 109.8(2) . . ?
N3A C4A C5A 108.43(8) . . ?
H4A C4A C41A 106.90(18) . . ?
N3A C4A C41A 111.75(9) . . ?
C5A C4A C41A 111.82(9) . . ?
O41A C41A O42A 125.15(13) . . ?
O41A C41A C4A 119.28(12) . . ?
O42A C41A C4A 115.57(11) . . ?
H51A C5A H52A 108.8(3) . . ?
H51A C5A C6A 109.3(2) . . ?
H52A C5A C6A 109.8(2) . . ?
H51A C5A C4A 110.7(2) . . ?
H52A C5A C4A 108.6(2) . . ?
C6A C5A C4A 109.58(10) . . ?
H62A C6A H61A 108.2(3) . . ?
H62A C6A N1A 107.7(2) . . ?
H61A C6A N1A 109.5(2) . . ?
H62A C6A C5A 110.9(2) . . ?
H61A C6A C5A 110.63(19) . . ?
N1A C6A C5A 109.86(9) . . ?
H11W O1W H12W 107.9(4) . . ?
H22W O2W H21W 108.0(4) . . ?

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
H1A N1A C2A N3A -178.4(2) . . . . ?
C6A N1A C2A N3A 3.85(16) . . . . ?
H1A N1A C2A C21A 2.4(3) . . . . ?
C6A N1A C2A C21A -175.42(10) . . . . ?
N1A C2A C21A H27A 64(3) . . . . ?
N3A C2A C21A H27A -115(3) . . . . ?
N1A C2A C21A H26A -120(3) . . . . ?
N3A C2A C21A H26A 61(3) . . . . ?
N1A C2A C21A H21A -150.3(15) . . . . ?
N3A C2A C21A H21A 30.4(15) . . . . ?
N1A C2A C21A H23A -26.8(13) . . . . ?
N3A C2A C21A H23A 153.9(13) . . . . ?
N1A C2A C21A H24A -1(2) . . . . ?
N3A C2A C21A H24A -180(2) . . . . ?
N1A C2A C21A H25A 114.9(17) . . . . ?
N3A C2A C21A H25A -64.4(17) . . . . ?
N1A C2A C21A H29A -173(2) . . . . ?
N3A C2A C21A H29A 8(2) . . . . ?
N1A C2A C21A H28A -55(2) . . . . ?
N3A C2A C21A H28A 126(2) . . . . ?
N1A C2A C21A H22A 88.4(11) . . . . ?
N3A C2A C21A H22A -90.9(11) . . . . ?
N1A C2A N3A H3A 179.7(2) . . . . ?
C21A C2A N3A H3A -1.0(3) . . . . ?
N1A C2A N3A C4A 3.42(16) . . . . ?
C21A C2A N3A C4A -177.32(10) . . . . ?
H3A N3A C4A H4A 31.3(3) . . . . ?
C2A N3A C4A H4A -152.4(2) . . . . ?
H3A N3A C4A C5A 150.2(2) . . . . ?
C2A N3A C4A C5A -33.41(13) . . . . ?
H3A N3A C4A C41A -86.1(2) . . . . ?
C2A N3A C4A C41A 90.29(11) . . . . ?
H4A C4A C41A O41A -120.1(3) . . . . ?
N3A C4A C41A O41A -2.01(17) . . . . ?
C5A C4A C41A O41A 119.76(15) . . . . ?
H4A C4A C41A O42A 60.8(2) . . . . ?
N3A C4A C41A O42A 178.83(11) . . . . ?
C5A C4A C41A O42A -59.41(14) . . . . ?
H4A C4A C5A H51A -66.5(3) . . . . ?
N3A C4A C5A H51A 175.6(2) . . . . ?
C41A C4A C5A H51A 51.9(2) . . . . ?
H4A C4A C5A H52A 52.9(3) . . . . ?
N3A C4A C5A H52A -65.0(2) . . . . ?
C41A C4A C5A H52A 171.4(2) . . . . ?
H4A C4A C5A C6A 172.9(2) . . . . ?
N3A C4A C5A C6A 55.01(11) . . . . ?
C41A C4A C5A C6A -68.65(12) . . . . ?
H1A N1A C6A H62A -36.4(3) . . . . ?
C2A N1A C6A H62A 141.4(3) . . . . ?
H1A N1A C6A H61A 81.0(3) . . . . ?
C2A N1A C6A H61A -101.2(2) . . . . ?
H1A N1A C6A C5A -157.3(2) . . . . ?
C2A N1A C6A C5A 20.51(14) . . . . ?
H51A C5A C6A H62A 70.5(3) . . . . ?
H52A C5A C6A H62A -48.8(3) . . . . ?
C4A C5A C6A H62A -168.0(2) . . . . ?
H51A C5A C6A H61A -49.5(3) . . . . ?
H52A C5A C6A H61A -168.8(3) . . . . ?
C4A C5A C6A H61A 72.0(2) . . . . ?
H51A C5A C6A N1A -170.5(2) . . . . ?
H52A C5A C6A N1A 70.1(3) . . . . ?
C4A C5A C6A N1A -49.07(12) . . . . ?

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
N1A H1A O42A 1.029(3) 1.802(3) 2.8185(16) 168.5(3) 2_665
N3A H3A O42A 1.026(3) 1.805(3) 2.8095(17) 165.1(3) 4_466
O1W H11W O41A 0.954(4) 1.870(4) 2.822(3) 176.7(4) .
O1W H12W O2W 0.963(4) 1.864(4) 2.812(3) 167.2(4) 4_456
O2W H21W O41A 0.971(4) 1.791(4) 2.762(2) 177.6(4) .
O2W H22W O42A 0.961(4) 2.093(4) 3.003(2) 157.3(4) 4_456

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.129


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
