# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_CGA-Form-I
_database_code_depnum_ccdc_archive 'CCDC 1043890'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 N-Carbamoyl-L-Glutamic Acid
;
_chemical_name_common            'Carglumic Acid'
_chemical_melting_point          '441 K'
_chemical_formula_moiety         'C6 H10 N2 O5'
_chemical_formula_sum            'C6 H10 N2 O5'
_chemical_formula_weight         190.16
_chemical_absolute_configuration rm

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_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                   5.1179(8)
_cell_length_b                   12.2079(18)
_cell_length_c                   12.7508(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     796.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6305
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.05

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8323
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         26.05
_reflns_number_total             1576
_reflns_number_gt                1532
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0315P)²+0.1747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_number_reflns         1576
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 0.459(5) -0.0892(18) 0.2619(17) 0.043(6) Uiso 1 1 d . . .
H2A H -0.104(4) 0.2595(16) 0.2553(14) 0.029(5) Uiso 1 1 d . . .
H5 H 0.897(4) -0.2075(18) 0.5580(15) 0.037(5) Uiso 1 1 d . . .
H2B H 0.068(3) 0.3414(14) 0.2054(14) 0.017(4) Uiso 1 1 d . . .
H6 H 0.073(4) 0.1281(14) 0.3592(13) 0.014(4) Uiso 1 1 d . . .
O4 O 0.8574(2) -0.13938(9) 0.58257(9) 0.0218(3) Uani 1 1 d . . .
O2 O 0.78475(19) 0.00611(8) 0.34998(8) 0.0174(2) Uani 1 1 d . . .
O1 O 0.3828(2) -0.02829(9) 0.28877(8) 0.0177(2) Uani 1 1 d . . .
O5 O 0.4712(2) 0.29047(8) 0.29116(8) 0.0175(2) Uani 1 1 d . . .
O3 O 0.4933(2) -0.16322(8) 0.48702(8) 0.0217(3) Uani 1 1 d . . .
N2 N 0.0458(3) 0.28334(11) 0.24147(10) 0.0181(3) Uani 1 1 d . . .
N1 N 0.2063(2) 0.16551(10) 0.36703(10) 0.0154(3) Uani 1 1 d . . .
C4 C 0.5505(3) 0.00347(11) 0.58313(11) 0.0179(3) Uani 1 1 d . . .
H4A H 0.7059 0.0517 0.5819 0.021 Uiso 1 1 calc R . .
H4B H 0.4930 -0.0030 0.6570 0.021 Uiso 1 1 calc R . .
C3 C 0.3327(3) 0.05799(12) 0.52005(11) 0.0168(3) Uani 1 1 d . . .
H3A H 0.2490 0.1147 0.5642 0.020 Uiso 1 1 calc R . .
H3B H 0.1984 0.0023 0.5033 0.020 Uiso 1 1 calc R . .
C1 C 0.5506(3) 0.02504(11) 0.34701(11) 0.0140(3) Uani 1 1 d . . .
C5 C 0.6290(3) -0.10802(12) 0.54451(11) 0.0165(3) Uani 1 1 d . . .
C6 C 0.2483(3) 0.24836(11) 0.29867(12) 0.0151(3) Uani 1 1 d . . .
C2 C 0.4252(3) 0.11125(11) 0.41757(11) 0.0151(3) Uani 1 1 d . . .
H2 H 0.557(3) 0.1661(12) 0.4311(11) 0.010(4) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0212(6) 0.0168(5) 0.0273(6) -0.0023(5) -0.0021(5) 0.0041(4)
O2 0.0125(5) 0.0182(5) 0.0214(5) -0.0003(4) 0.0007(4) -0.0003(4)
O1 0.0148(5) 0.0184(5) 0.0200(5) -0.0054(5) -0.0021(4) 0.0011(4)
O5 0.0138(5) 0.0167(5) 0.0219(5) 0.0036(4) -0.0007(5) -0.0012(4)
O3 0.0257(6) 0.0155(5) 0.0239(5) -0.0001(4) -0.0030(5) -0.0013(4)
N2 0.0146(7) 0.0185(6) 0.0213(6) 0.0039(5) -0.0003(6) -0.0015(5)
N1 0.0106(6) 0.0130(6) 0.0227(7) -0.0004(5) -0.0014(5) -0.0025(5)
C4 0.0188(7) 0.0180(7) 0.0167(6) -0.0003(6) 0.0001(6) -0.0003(6)
C3 0.0170(7) 0.0168(7) 0.0168(7) -0.0014(6) 0.0026(6) 0.0015(5)
C1 0.0150(7) 0.0137(6) 0.0134(6) 0.0035(5) 0.0008(6) -0.0018(6)
C5 0.0180(7) 0.0155(7) 0.0159(7) 0.0040(6) 0.0020(6) -0.0022(6)
C6 0.0142(7) 0.0146(6) 0.0166(7) -0.0053(6) 0.0006(6) 0.0014(6)
C2 0.0133(7) 0.0129(6) 0.0192(7) 0.0007(6) -0.0013(6) -0.0016(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
O4 C5 1.3221(18) . ?
O4 H5 0.91(2) . ?
O2 C1 1.2212(18) . ?
O1 C1 1.3087(17) . ?
O1 H1 0.91(2) . ?
O5 C6 1.2550(17) . ?
O3 C5 1.2140(18) . ?
N2 C6 1.337(2) . ?
N2 H2A 0.84(2) . ?
N2 H2B 0.853(18) . ?
N1 C6 1.3524(19) . ?
N1 C2 1.4519(18) . ?
N1 H6 0.827(19) . ?
C4 C5 1.502(2) . ?
C4 C3 1.527(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C3 C2 1.534(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 C2 1.5261(19) . ?
C2 H2 0.965(15) . ?

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
C5 O4 H5 109.5(13) . . ?
C1 O1 H1 110.0(15) . . ?
C6 N2 H2A 118.8(13) . . ?
C6 N2 H2B 117.1(11) . . ?
H2A N2 H2B 121.7(17) . . ?
C6 N1 C2 120.32(12) . . ?
C6 N1 H6 117.8(11) . . ?
C2 N1 H6 116.0(12) . . ?
C5 C4 C3 114.68(12) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C3 C2 114.07(12) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O2 C1 O1 124.57(13) . . ?
O2 C1 C2 121.66(13) . . ?
O1 C1 C2 113.68(12) . . ?
O3 C5 O4 124.51(14) . . ?
O3 C5 C4 123.22(13) . . ?
O4 C5 C4 112.25(13) . . ?
O5 C6 N2 122.15(14) . . ?
O5 C6 N1 119.99(13) . . ?
N2 C6 N1 117.86(13) . . ?
N1 C2 C1 112.17(12) . . ?
N1 C2 C3 109.47(11) . . ?
C1 C2 C3 109.85(11) . . ?
N1 C2 H2 107.5(9) . . ?
C1 C2 H2 106.9(9) . . ?
C3 C2 H2 110.9(9) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.05
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeOH : 2-butanone '
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_CGA-Form-II
_database_code_depnum_ccdc_archive 'CCDC 1043891'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 N-Carbamoyl-L-Glutamic Acid
;
_chemical_name_common            'Carglumic Acid'
_chemical_melting_point          '434 K'
_chemical_formula_moiety         'C6 H10 N2 O5'
_chemical_formula_sum            'C6 H10 N2 O5'
_chemical_formula_weight         190.16
_chemical_absolute_configuration rm
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.3615(5)
_cell_length_b                   15.8123(15)
_cell_length_c                   9.9631(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.899(2)
_cell_angle_gamma                90.00
_cell_volume                     844.54(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3817
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.97

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8820
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         26.06
_reflns_number_total             3335
_reflns_number_gt                3159
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.0482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(8)
_refine_ls_number_reflns         3335
_refine_ls_number_parameters     283
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O10 O -0.0085(2) 0.50166(9) -0.12580(12) 0.0206(3) Uani 1 1 d . . .
O3 O 0.7461(2) 0.79317(8) 0.02064(12) 0.0195(3) Uani 1 1 d . . .
O5 O 0.4937(2) 0.81812(9) 0.70877(12) 0.0204(3) Uani 1 1 d . . .
O6 O 0.0252(2) 0.66005(9) 0.08005(13) 0.0215(3) Uani 1 1 d . . .
O4 O 0.3603(2) 0.82830(9) -0.04334(13) 0.0233(3) Uani 1 1 d . . .
N2 N 0.9110(3) 0.80149(11) 0.74357(16) 0.0211(3) Uani 1 1 d D . .
O9 O -0.1318(2) 0.48653(9) 0.62624(13) 0.0227(3) Uani 1 1 d . . .
O1 O 0.5300(2) 0.65953(9) 0.50082(13) 0.0204(3) Uani 1 1 d . . .
N1 N 0.7477(3) 0.81237(11) 0.52982(14) 0.0167(3) Uani 1 1 d . . .
O7 O -0.3351(2) 0.60248(9) 0.14265(13) 0.0231(3) Uani 1 1 d . . .
O8 O 0.2475(2) 0.52823(9) 0.56835(12) 0.0203(3) Uani 1 1 d . . .
O2 O 0.1665(2) 0.71831(9) 0.44250(13) 0.0232(3) Uani 1 1 d . . .
N4 N 0.4113(3) 0.50953(11) -0.15120(16) 0.0221(4) Uani 1 1 d . . .
C12 C 0.2061(3) 0.50693(11) -0.07570(17) 0.0174(4) Uani 1 1 d . . .
N3 N 0.2437(3) 0.50705(10) 0.05826(14) 0.0175(3) Uani 1 1 d . . .
C9 C 0.1359(3) 0.51806(12) 0.29233(16) 0.0167(4) Uani 1 1 d . . .
H9A H 0.2546 0.4723 0.3045 0.020 Uiso 1 1 calc R . .
H9B H 0.2242 0.5709 0.3072 0.020 Uiso 1 1 calc R . .
C3 C 0.6355(3) 0.80488(12) 0.29408(16) 0.0174(4) Uani 1 1 d . . .
H3A H 0.7360 0.8552 0.2816 0.021 Uiso 1 1 calc R . .
H3B H 0.7427 0.7561 0.2820 0.021 Uiso 1 1 calc R . .
C1 C 0.3895(3) 0.72354(12) 0.46242(17) 0.0175(4) Uani 1 1 d . . .
C2 C 0.5366(3) 0.80432(12) 0.43775(17) 0.0167(4) Uani 1 1 d . . .
C8 C 0.0330(3) 0.51610(13) 0.14732(16) 0.0171(4) Uani 1 1 d . . .
C5 C 0.5279(3) 0.80776(12) 0.04786(17) 0.0176(4) Uani 1 1 d . . .
C7 C -0.1135(3) 0.59656(12) 0.12130(17) 0.0180(4) Uani 1 1 d . . .
C6 C 0.7093(3) 0.80974(12) 0.66356(17) 0.0180(4) Uani 1 1 d . . .
C11 C 0.0326(3) 0.50954(12) 0.53773(17) 0.0175(4) Uani 1 1 d . . .
C10 C -0.0681(3) 0.50959(13) 0.39564(16) 0.0189(4) Uani 1 1 d . . .
H10A H -0.1847 0.5561 0.3847 0.023 Uiso 1 1 calc R . .
H10B H -0.1587 0.4574 0.3795 0.023 Uiso 1 1 calc R . .
C4 C 0.4290(3) 0.80313(12) 0.18783(16) 0.0180(4) Uani 1 1 d . . .
H4A H 0.3333 0.7515 0.1974 0.022 Uiso 1 1 calc R . .
H4B H 0.3174 0.8504 0.2022 0.022 Uiso 1 1 calc R . .
H2B H 0.885(4) 0.7981(14) 0.828(2) 0.016(5) Uiso 1 1 d . . .
H12 H 0.378(4) 0.5222(16) 0.090(2) 0.028(6) Uiso 1 1 d . . .
H5 H 0.419(5) 0.8263(18) -0.121(3) 0.041(7) Uiso 1 1 d . . .
H6 H 0.878(4) 0.7876(14) 0.502(2) 0.018(5) Uiso 1 1 d . . .
H13A H 0.399(4) 0.5144(15) -0.238(2) 0.023(5) Uiso 1 1 d . . .
H13B H 0.549(4) 0.5151(14) -0.116(2) 0.021(6) Uiso 1 1 d . . .
H1 H 0.439(4) 0.6193(17) 0.513(2) 0.030(7) Uiso 1 1 d . . .
H11 H -0.073(5) 0.4944(17) 0.716(3) 0.047(7) Uiso 1 1 d . . .
H7 H -0.063(5) 0.7036(17) 0.075(2) 0.031(6) Uiso 1 1 d . . .
H2 H 0.426(4) 0.8511(14) 0.451(2) 0.015(5) Uiso 1 1 d . . .
H8 H -0.074(3) 0.4680(13) 0.1354(18) 0.009(4) Uiso 1 1 d . . .
H2A H 1.046(3) 0.7948(15) 0.707(2) 0.021(6) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O10 0.0172(7) 0.0296(8) 0.0150(6) -0.0003(5) -0.0005(5) -0.0011(6)
O3 0.0176(6) 0.0242(7) 0.0167(6) 0.0025(5) 0.0008(5) 0.0034(5)
O5 0.0165(6) 0.0292(8) 0.0155(6) -0.0006(6) 0.0008(5) 0.0011(6)
O6 0.0180(6) 0.0200(7) 0.0266(7) 0.0040(6) -0.0003(5) 0.0016(6)
O4 0.0191(7) 0.0375(8) 0.0132(7) -0.0003(6) -0.0003(5) 0.0037(6)
N2 0.0164(8) 0.0329(9) 0.0142(8) 0.0010(7) 0.0021(6) 0.0024(7)
O9 0.0204(7) 0.0345(8) 0.0132(6) 0.0006(6) 0.0012(5) -0.0066(6)
O1 0.0167(6) 0.0192(7) 0.0253(7) 0.0038(6) 0.0006(5) -0.0016(6)
N1 0.0156(7) 0.0205(8) 0.0141(7) -0.0015(7) 0.0025(6) 0.0012(7)
O7 0.0153(7) 0.0261(7) 0.0279(7) 0.0015(6) -0.0006(6) 0.0005(5)
O8 0.0184(7) 0.0266(7) 0.0160(6) 0.0026(5) -0.0008(5) -0.0039(5)
O2 0.0155(6) 0.0291(7) 0.0251(7) -0.0004(6) 0.0004(5) -0.0004(6)
N4 0.0177(9) 0.0339(10) 0.0144(8) -0.0023(7) -0.0021(6) -0.0020(7)
C12 0.0210(9) 0.0154(9) 0.0158(8) -0.0002(7) 0.0000(7) 0.0007(7)
N3 0.0159(8) 0.0212(8) 0.0153(7) -0.0022(6) -0.0014(6) 0.0002(7)
C9 0.0169(9) 0.0185(9) 0.0147(8) -0.0005(7) -0.0010(7) -0.0008(7)
C3 0.0179(9) 0.0195(9) 0.0150(8) -0.0006(8) 0.0014(7) -0.0014(8)
C1 0.0169(9) 0.0240(9) 0.0115(8) -0.0031(7) 0.0021(7) 0.0025(8)
C2 0.0175(9) 0.0171(9) 0.0156(8) -0.0012(7) 0.0007(7) 0.0034(8)
C8 0.0166(8) 0.0203(9) 0.0142(8) 0.0001(7) 0.0007(7) -0.0030(8)
C5 0.0188(9) 0.0159(9) 0.0181(8) -0.0011(8) -0.0021(7) -0.0001(7)
C7 0.0184(9) 0.0242(9) 0.0112(8) -0.0014(7) -0.0013(7) -0.0020(8)
C6 0.0200(9) 0.0163(10) 0.0177(8) -0.0006(8) 0.0015(7) -0.0010(7)
C11 0.0198(9) 0.0170(9) 0.0158(8) -0.0012(7) 0.0010(7) 0.0003(8)
C10 0.0169(9) 0.0241(10) 0.0158(8) 0.0011(8) 0.0006(7) -0.0008(8)
C4 0.0177(9) 0.0202(9) 0.0160(8) 0.0005(8) 0.0015(7) 0.0002(8)

_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
O10 C12 1.250(2) . ?
O3 C5 1.227(2) . ?
O5 C6 1.254(2) . ?
O6 C7 1.319(2) . ?
O6 H7 0.84(3) . ?
O4 C5 1.309(2) . ?
O4 H5 0.84(3) . ?
N2 C6 1.340(2) . ?
N2 H2B 0.86(2) . ?
N2 H2A 0.818(16) . ?
O9 C11 1.308(2) . ?
O9 H11 0.95(3) . ?
O1 C1 1.315(2) . ?
O1 H1 0.81(3) . ?
N1 C6 1.352(2) . ?
N1 C2 1.451(2) . ?
N1 H6 0.85(2) . ?
O7 C7 1.214(2) . ?
O8 C11 1.224(2) . ?
O2 C1 1.212(2) . ?
N4 C12 1.343(2) . ?
N4 H13A 0.87(2) . ?
N4 H13B 0.82(2) . ?
C12 N3 1.347(2) . ?
N3 C8 1.454(2) . ?
N3 H12 0.82(2) . ?
C9 C10 1.520(2) . ?
C9 C8 1.539(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 C4 1.520(2) . ?
C3 C2 1.534(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 C2 1.523(3) . ?
C2 H2 0.96(2) . ?
C8 C7 1.515(3) . ?
C8 H8 0.96(2) . ?
C5 C4 1.502(2) . ?
C11 C10 1.507(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?

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
C7 O6 H7 108.9(17) . . ?
C5 O4 H5 111.5(17) . . ?
C6 N2 H2B 116.6(13) . . ?
C6 N2 H2A 117.4(14) . . ?
H2B N2 H2A 126(2) . . ?
C11 O9 H11 112.3(15) . . ?
C1 O1 H1 107.6(17) . . ?
C6 N1 C2 119.40(15) . . ?
C6 N1 H6 116.6(14) . . ?
C2 N1 H6 112.8(14) . . ?
C12 N4 H13A 120.6(13) . . ?
C12 N4 H13B 120.1(15) . . ?
H13A N4 H13B 118(2) . . ?
O10 C12 N4 122.38(16) . . ?
O10 C12 N3 121.21(16) . . ?
N4 C12 N3 116.36(16) . . ?
C12 N3 C8 119.95(14) . . ?
C12 N3 H12 120.2(17) . . ?
C8 N3 H12 114.9(17) . . ?
C10 C9 C8 112.50(14) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C4 C3 C2 113.01(15) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O2 C1 O1 123.67(17) . . ?
O2 C1 C2 122.89(16) . . ?
O1 C1 C2 113.36(15) . . ?
N1 C2 C1 111.86(15) . . ?
N1 C2 C3 108.16(15) . . ?
C1 C2 C3 110.05(14) . . ?
N1 C2 H2 109.0(12) . . ?
C1 C2 H2 107.5(12) . . ?
C3 C2 H2 110.2(12) . . ?
N3 C8 C7 112.56(15) . . ?
N3 C8 C9 107.71(14) . . ?
C7 C8 C9 108.72(15) . . ?
N3 C8 H8 108.5(11) . . ?
C7 C8 H8 109.6(11) . . ?
C9 C8 H8 109.7(11) . . ?
O3 C5 O4 122.69(16) . . ?
O3 C5 C4 123.24(15) . . ?
O4 C5 C4 114.07(15) . . ?
O7 C7 O6 123.63(18) . . ?
O7 C7 C8 122.74(17) . . ?
O6 C7 C8 113.55(16) . . ?
O5 C6 N2 122.46(16) . . ?
O5 C6 N1 120.41(16) . . ?
N2 C6 N1 117.08(16) . . ?
O8 C11 O9 122.75(15) . . ?
O8 C11 C10 123.79(16) . . ?
O9 C11 C10 113.45(15) . . ?
C11 C10 C9 112.65(14) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C5 C4 C3 112.44(14) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.06
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.046
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH3CN: m-cresol '
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_5-HPA
_database_code_depnum_ccdc_archive 'CCDC 1043892'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '3-(2,5-dioxoimidazolidin-4-yl) propanoic acid' 
;
_chemical_name_common            'Hydantoin-5-propionic acid'
_chemical_melting_point          '425 K'
_chemical_formula_moiety         'C6 H8 N2 O4'
_chemical_formula_sum            'C6 H8 N2 O4'
_chemical_formula_weight         172.14
_chemical_absolute_configuration rm

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.2475(4)
_cell_length_b                   7.1111(6)
_cell_length_c                   17.3692(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.792(5)
_cell_angle_gamma                90.00
_cell_volume                     766.24(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1548
_cell_measurement_theta_min      4.2820
_cell_measurement_theta_max      28.0310

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
 CrysAlisPro, Oxford Diffraction Ltd.,
 Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
 (compiled Jan 5 2010,16:28:46)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3077
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         26.36
_reflns_number_total             2191
_reflns_number_gt                1973
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0427P)²+0.0378P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(12)
_refine_ls_number_reflns         2191
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.5918(3) 0.2679(4) 0.99296(11) 0.0421(6) Uani 1 1 d . . .
O4 O -0.3171(2) 0.4947(3) 0.35683(9) 0.0446(5) Uani 1 1 d . . .
O6 O 0.5975(3) 0.4987(4) 0.70972(10) 0.0603(6) Uani 1 1 d . . .
C11 C 0.9532(3) 0.2539(4) 0.98249(13) 0.0365(6) Uani 1 1 d . . .
O8 O 1.1269(2) 0.2468(4) 0.95794(10) 0.0577(7) Uani 1 1 d . . .
O1 O 0.5372(2) 0.6682(3) 0.57327(11) 0.0433(4) Uani 1 1 d . . .
N4 N 0.9166(3) 0.2863(3) 1.05633(11) 0.0380(5) Uani 1 1 d . . .
H12 H 1.0167 0.2985 1.0945 0.046 Uiso 1 1 calc R . .
N2 N -0.1095(3) 0.4253(3) 0.25981(10) 0.0370(5) Uani 1 1 d . . .
N1 N 0.2166(3) 0.4735(4) 0.31908(10) 0.0375(5) Uani 1 1 d . . .
O3 O 0.1840(2) 0.3863(3) 0.19101(8) 0.0484(5) Uani 1 1 d . . .
O2 O 0.1932(2) 0.5833(3) 0.57067(10) 0.0520(5) Uani 1 1 d . . .
C7 C 0.4522(3) 0.4360(4) 0.74315(14) 0.0427(6) Uani 1 1 d . . .
C4 C 0.0756(3) 0.5066(4) 0.37860(12) 0.0314(5) Uani 1 1 d . . .
H4 H 0.1016 0.4121 0.4197 0.038 Uiso 1 1 calc R . .
C1 C 0.3388(3) 0.6556(4) 0.53977(13) 0.0360(5) Uani 1 1 d . . .
O5 O 0.2494(3) 0.4516(4) 0.71562(11) 0.0637(7) Uani 1 1 d . . .
C12 C 0.6976(3) 0.2974(4) 1.06328(13) 0.0392(6) Uani 1 1 d . . .
C9 C 0.7046(3) 0.3628(4) 0.86485(13) 0.0423(6) Uani 1 1 d . . .
H9A H 0.8182 0.3406 0.8324 0.051 Uiso 1 1 calc R . .
H9B H 0.7149 0.4924 0.8823 0.051 Uiso 1 1 calc R . .
O7 O 0.6215(2) 0.3280(4) 1.12371(10) 0.0641(7) Uani 1 1 d . . .
C10 C 0.7340(3) 0.2319(4) 0.93453(12) 0.0336(6) Uani 1 1 d . . .
H10 H 0.7161 0.1014 0.9168 0.040 Uiso 1 1 calc R . .
C3 C 0.0919(4) 0.7025(4) 0.41293(14) 0.0380(6) Uani 1 1 d . . .
H3A H -0.0237 0.7192 0.4450 0.046 Uiso 1 1 calc R . .
H3B H 0.0699 0.7932 0.3710 0.046 Uiso 1 1 calc R . .
C5 C -0.1443(3) 0.4747(4) 0.33202(12) 0.0317(5) Uani 1 1 d . . .
C6 C 0.1103(3) 0.4240(4) 0.25109(12) 0.0337(5) Uani 1 1 d . . .
C8 C 0.4865(4) 0.3302(5) 0.81789(14) 0.0483(7) Uani 1 1 d . . .
H8A H 0.4707 0.1969 0.8068 0.058 Uiso 1 1 calc R . .
H8B H 0.3745 0.3656 0.8493 0.058 Uiso 1 1 calc R . .
C2 C 0.3049(4) 0.7458(4) 0.46149(13) 0.0418(6) Uani 1 1 d . . .
H2A H 0.4210 0.7068 0.4326 0.050 Uiso 1 1 calc R . .
H2B H 0.3161 0.8810 0.4683 0.050 Uiso 1 1 calc R . .
H5 H 0.355(4) 0.476(4) 0.3284(13) 0.040(7) Uiso 1 1 d . . .
H11 H 0.459(5) 0.259(4) 0.9892(15) 0.043(8) Uiso 1 1 d . . .
H6 H -0.202(3) 0.402(4) 0.2196(13) 0.028(6) Uiso 1 1 d . . .
H7 H 0.243(5) 0.505(7) 0.664(2) 0.098(13) Uiso 1 1 d . . .
H1 H 0.543(5) 0.605(7) 0.624(3) 0.120(15) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N3 0.0197(9) 0.0733(18) 0.0328(10) -0.0061(11) 0.0011(7) -0.0009(11)
O4 0.0210(7) 0.0716(14) 0.0421(9) -0.0023(10) 0.0068(6) -0.0021(8)
O6 0.0454(9) 0.0906(18) 0.0425(10) 0.0171(12) -0.0053(7) -0.0069(11)
C11 0.0259(11) 0.0469(15) 0.0359(13) -0.0019(12) 0.0002(8) 0.0007(11)
O8 0.0220(7) 0.109(2) 0.0426(9) -0.0065(12) 0.0059(6) 0.0011(10)
O1 0.0323(8) 0.0517(12) 0.0438(10) -0.0060(10) -0.0044(7) -0.0005(8)
N4 0.0213(8) 0.0605(15) 0.0311(10) -0.0048(11) -0.0015(7) 0.0006(9)
N2 0.0224(8) 0.0592(15) 0.0286(10) -0.0020(10) -0.0003(7) -0.0024(9)
N1 0.0189(8) 0.0596(15) 0.0337(10) -0.0034(10) 0.0018(6) 0.0012(9)
O3 0.0299(8) 0.0846(16) 0.0309(8) -0.0075(10) 0.0045(6) 0.0018(9)
O2 0.0431(9) 0.0650(14) 0.0446(10) 0.0131(10) -0.0084(7) -0.0173(10)
C7 0.0382(12) 0.0500(17) 0.0372(12) -0.0045(13) -0.0069(9) -0.0027(12)
C4 0.0249(10) 0.0421(14) 0.0265(10) 0.0051(11) 0.0005(7) 0.0017(10)
C1 0.0356(11) 0.0318(13) 0.0393(13) -0.0056(12) -0.0018(9) -0.0017(11)
O5 0.0429(9) 0.095(2) 0.0482(11) 0.0191(13) -0.0138(7) -0.0047(11)
C12 0.0244(10) 0.0601(18) 0.0326(12) -0.0037(13) 0.0020(8) -0.0010(11)
C9 0.0345(12) 0.0574(18) 0.0333(12) -0.0002(13) -0.0029(9) -0.0075(12)
O7 0.0318(8) 0.125(2) 0.0360(9) -0.0160(13) 0.0059(7) -0.0019(11)
C10 0.0249(10) 0.0459(15) 0.0295(11) -0.0043(11) 0.0017(8) 0.0006(10)
C3 0.0365(12) 0.0443(15) 0.0320(12) 0.0025(11) -0.0011(9) 0.0061(11)
C5 0.0235(9) 0.0392(14) 0.0319(11) 0.0043(11) 0.0015(7) -0.0016(10)
C6 0.0261(10) 0.0456(15) 0.0294(11) 0.0016(11) 0.0024(8) 0.0014(10)
C8 0.0383(12) 0.065(2) 0.0393(13) 0.0045(14) -0.0071(9) -0.0062(13)
C2 0.0422(12) 0.0434(15) 0.0389(13) 0.0000(12) 0.0014(10) -0.0077(12)

_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
N3 C12 1.335(3) . ?
N3 C10 1.449(3) . ?
O4 C5 1.217(2) . ?
O6 C7 1.218(3) . ?
C11 O8 1.213(3) . ?
C11 N4 1.349(3) . ?
C11 C10 1.524(3) . ?
O1 C1 1.309(3) . ?
N4 C12 1.390(3) . ?
N2 C5 1.345(3) . ?
N2 C6 1.399(3) . ?
N1 C6 1.332(3) . ?
N1 C4 1.454(3) . ?
O3 C6 1.219(2) . ?
O2 C1 1.223(3) . ?
C7 O5 1.305(3) . ?
C7 C8 1.494(4) . ?
C4 C3 1.515(3) . ?
C4 C5 1.527(3) . ?
C1 C2 1.496(3) . ?
C12 O7 1.222(3) . ?
C9 C10 1.520(3) . ?
C9 C8 1.521(3) . ?
C3 C2 1.521(3) . ?

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
C12 N3 C10 112.96(18) . . ?
O8 C11 N4 126.90(19) . . ?
O8 C11 C10 125.9(2) . . ?
N4 C11 C10 107.15(17) . . ?
C11 N4 C12 111.81(17) . . ?
C5 N2 C6 111.83(17) . . ?
C6 N1 C4 113.12(16) . . ?
O6 C7 O5 122.7(2) . . ?
O6 C7 C8 124.1(2) . . ?
O5 C7 C8 113.2(2) . . ?
N1 C4 C3 114.2(2) . . ?
N1 C4 C5 100.49(16) . . ?
C3 C4 C5 111.07(19) . . ?
O2 C1 O1 123.2(2) . . ?
O2 C1 C2 123.2(2) . . ?
O1 C1 C2 113.5(2) . . ?
O7 C12 N3 127.8(2) . . ?
O7 C12 N4 124.9(2) . . ?
N3 C12 N4 107.33(18) . . ?
C10 C9 C8 110.5(2) . . ?
N3 C10 C9 115.0(2) . . ?
N3 C10 C11 100.66(17) . . ?
C9 C10 C11 112.9(2) . . ?
C4 C3 C2 114.7(2) . . ?
O4 C5 N2 127.52(18) . . ?
O4 C5 C4 125.1(2) . . ?
N2 C5 C4 107.35(16) . . ?
O3 C6 N1 128.16(18) . . ?
O3 C6 N2 124.67(19) . . ?
N1 C6 N2 107.16(17) . . ?
C7 C8 C9 114.6(2) . . ?
C1 C2 C3 116.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.042
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 2-butanone: propionic acid '
_chemical_compound_source        synthetic
