# 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_doxaiso
_database_code_depnum_ccdc_archive 'CCDC 1043942'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'bis(isonicotinamide)-d-oxalic acid Form I'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2[DC6H4D2N2O]+ [C2O4]2'
_chemical_formula_sum            'C14 H8 D6 N4 O6'
_chemical_formula_weight         340.33

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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.7233(3)
_cell_length_b                   7.4294(5)
_cell_length_c                   12.3158(10)
_cell_angle_alpha                98.262(4)
_cell_angle_beta                 90.019(4)
_cell_angle_gamma                91.709(5)
_cell_volume                     336.99(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5440
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      36.29

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             174
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_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            10173
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         33.99
_reflns_number_total             2744
_reflns_number_gt                2505
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker AXS X8 Apex2'
_computing_cell_refinement       'Bruker AXS SAINT V7.34A'
_computing_data_reduction        'Bruker AXS SAINT V7.34A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker AXS XP'
_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)+(0.0600P)²+0.0400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2744
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.92658(16) 0.22578(7) 0.48418(4) 0.01706(12) Uani 1 1 d . . .
O2 O 1.07184(15) -0.00976(7) 0.35855(4) 0.01486(11) Uani 1 1 d . . .
O3 O 0.19641(15) 0.77292(7) 0.99444(4) 0.01601(12) Uani 1 1 d . . .
N1 N 0.62643(16) 0.34963(8) 0.67990(5) 0.01449(12) Uani 1 1 d . . .
D1 D 0.720(5) 0.247(3) 0.6301(16) 0.068(5) Uiso 1 1 d . . .
N2 N 0.08291(16) 0.92982(7) 0.85367(4) 0.01285(11) Uani 1 1 d . . .
C1 C 0.99897(17) 0.06335(8) 0.45467(5) 0.01112(12) Uani 1 1 d . . .
C2 C 0.50076(18) 0.31948(9) 0.77792(6) 0.01418(13) Uani 1 1 d . . .
H2 H 0.523(4) 0.1983(17) 0.7951(10) 0.025(3) Uiso 1 1 d . . .
C3 C 0.35609(17) 0.46001(8) 0.84847(5) 0.01187(12) Uani 1 1 d . . .
H3 H 0.271(4) 0.4349(19) 0.9190(11) 0.030(3) Uiso 1 1 d . . .
C4 C 0.34116(16) 0.63174(8) 0.81578(5) 0.00964(11) Uani 1 1 d . . .
C5 C 0.47212(18) 0.65815(9) 0.71315(5) 0.01197(12) Uani 1 1 d . . .
H4 H 0.475(3) 0.7726(17) 0.6869(10) 0.022(3) Uiso 1 1 d . . .
C6 C 0.61692(18) 0.51276(9) 0.64636(5) 0.01412(12) Uani 1 1 d . . .
H5 H 0.726(4) 0.5221(18) 0.5777(11) 0.030(3) Uiso 1 1 d . . .
C7 C 0.19788(17) 0.78590(8) 0.89535(5) 0.01058(12) Uani 1 1 d . . .
D6 D -0.013(4) 1.0244(18) 0.9051(11) 0.030(3) Uiso 1 1 d . . .
D7 D 0.055(4) 0.9289(18) 0.7811(11) 0.025(3) 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
O1 0.0291(3) 0.0107(2) 0.0118(2) 0.00160(16) 0.00407(18) 0.00741(18)
O2 0.0237(3) 0.0128(2) 0.0082(2) 0.00104(15) 0.00321(16) 0.00501(17)
O3 0.0256(3) 0.0144(2) 0.0084(2) 0.00144(16) 0.00156(17) 0.00723(18)
N1 0.0125(2) 0.0138(2) 0.0151(3) -0.00499(19) 0.00029(18) 0.00265(18)
N2 0.0196(3) 0.0097(2) 0.0095(2) 0.00104(17) 0.00038(18) 0.00509(18)
C1 0.0141(3) 0.0108(2) 0.0086(2) 0.00119(18) 0.00139(18) 0.00324(19)
C2 0.0148(3) 0.0097(2) 0.0173(3) -0.0007(2) -0.0003(2) 0.00225(19)
C3 0.0141(3) 0.0095(2) 0.0121(3) 0.00162(19) 0.00069(19) 0.00215(18)
C4 0.0111(2) 0.0091(2) 0.0087(2) 0.00059(17) 0.00009(17) 0.00183(17)
C5 0.0141(3) 0.0126(2) 0.0091(2) 0.00086(19) 0.00108(19) 0.00160(19)
C6 0.0141(3) 0.0173(3) 0.0100(2) -0.0017(2) 0.00164(19) 0.0016(2)
C7 0.0132(3) 0.0090(2) 0.0094(2) 0.00037(18) 0.00063(18) 0.00256(18)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2468(8) . ?
O2 C1 1.2626(8) . ?
O3 C7 1.2378(7) . ?
N1 C6 1.3369(9) . ?
N1 C2 1.3410(9) . ?
N1 D1 0.98(2) . ?
N2 D7 0.898(13) . ?
N2 D6 0.953(14) . ?
N2 C7 1.3322(8) . ?
C1 C1 1.5605(12) 2_756 ?
C2 H2 0.960(13) . ?
C2 C3 1.3814(9) . ?
C3 H3 0.967(13) . ?
C3 C4 1.3946(8) . ?
C4 C5 1.3928(8) . ?
C4 C7 1.5070(8) . ?
C5 H4 0.952(12) . ?
C5 C6 1.3833(9) . ?
C6 H5 0.948(14) . ?

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
C6 N1 C2 122.40(6) . . ?
C6 N1 D1 118.9(11) . . ?
C2 N1 D1 118.6(11) . . ?
D7 N2 D6 120.9(12) . . ?
D7 N2 C7 122.1(9) . . ?
D6 N2 C7 115.9(8) . . ?
O1 C1 O2 126.64(6) . . ?
O1 C1 C1 117.04(7) . 2_756 ?
O2 C1 C1 116.32(7) . 2_756 ?
H2 C2 N1 116.3(8) . . ?
H2 C2 C3 123.8(8) . . ?
N1 C2 C3 119.96(6) . . ?
H3 C3 C2 118.2(8) . . ?
H3 C3 C4 122.7(8) . . ?
C2 C3 C4 119.05(6) . . ?
C5 C4 C3 119.52(6) . . ?
C5 C4 C7 121.85(5) . . ?
C3 C4 C7 118.57(5) . . ?
H4 C5 C6 117.6(8) . . ?
H4 C5 C4 123.5(8) . . ?
C6 C5 C4 118.88(6) . . ?
H5 C6 N1 116.0(8) . . ?
H5 C6 C5 123.7(8) . . ?
N1 C6 C5 120.19(6) . . ?
O3 C7 N2 124.02(6) . . ?
O3 C7 C4 118.85(5) . . ?
N2 C7 C4 117.13(5) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        33.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.067
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: D2O'
####################################################################### 
# 
# 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_doxaiso2
_database_code_depnum_ccdc_archive 'CCDC 1043943'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'bis(isonicotinamide)-d-oxalic acid Form II'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6H4D2N2O [DC6H4D2N2O]+ [DC2O4]'
_chemical_formula_sum            'C14 H8 D6 N4 O6'
_chemical_formula_weight         340.33

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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9765(7)
_cell_length_b                   8.1978(8)
_cell_length_c                   13.1421(10)
_cell_angle_alpha                106.725(5)
_cell_angle_beta                 92.458(5)
_cell_angle_gamma                105.171(6)
_cell_volume                     689.04(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2348
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      33.92

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'

_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            14726
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         34.11
_reflns_number_total             5595
_reflns_number_gt                3329
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker AXS X8 Apex2'
_computing_cell_refinement       'Bruker AXS SAINT V7.34A'
_computing_data_reduction        'Bruker AXS SAINT V7.34A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker AXS XP'
_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)+(0.0750P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5595
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
O1 O 0.32131(14) 0.19196(11) 0.34694(7) 0.01664(19) Uani 1 1 d . . .
O2 O 0.02985(13) -0.01507(11) 0.30469(6) 0.01492(18) Uani 1 1 d . . .
O3 O 0.46469(13) -0.00537(11) 0.18278(6) 0.01506(19) Uani 1 1 d . . .
O4 O 0.17105(13) -0.21964(11) 0.14237(7) 0.01691(19) Uani 1 1 d . . .
O5 O 1.38235(13) 0.78581(11) 0.39281(6) 0.01656(19) Uani 1 1 d . . .
O6 O -0.88415(13) -0.78509(11) 0.10533(6) 0.01622(19) Uani 1 1 d . . .
N1 N 0.68929(15) 0.37515(13) 0.34338(7) 0.0130(2) Uani 1 1 d . . .
N2 N 1.25066(16) 0.92831(13) 0.53441(7) 0.0133(2) Uani 1 1 d . . .
N3 N -0.19850(15) -0.38078(13) 0.15679(7) 0.0127(2) Uani 1 1 d . . .
N4 N -0.75073(16) -0.92572(13) -0.03682(7) 0.0131(2) Uani 1 1 d . . .
C1 C 0.20165(17) 0.03928(15) 0.28787(8) 0.0117(2) Uani 1 1 d . . .
C2 C 0.28883(17) -0.07256(15) 0.19547(8) 0.0118(2) Uani 1 1 d . . .
C3 C 0.86404(18) 0.34840(15) 0.31511(9) 0.0130(2) Uani 1 1 d . . .
C4 C 1.04454(18) 0.48075(15) 0.34688(9) 0.0124(2) Uani 1 1 d . . .
C5 C 1.04658(17) 0.64873(14) 0.41157(8) 0.0105(2) Uani 1 1 d . . .
C6 C 0.86644(17) 0.67731(14) 0.44097(8) 0.0121(2) Uani 1 1 d . . .
C7 C 0.69288(18) 0.53767(15) 0.40493(9) 0.0130(2) Uani 1 1 d . . .
C8 C 1.24125(17) 0.79398(14) 0.44629(8) 0.0112(2) Uani 1 1 d . . .
C9 C -0.36933(18) -0.34794(15) 0.18659(9) 0.0135(2) Uani 1 1 d . . .
C10 C -0.54793(18) -0.48219(15) 0.15387(9) 0.0125(2) Uani 1 1 d . . .
C11 C -0.54725(17) -0.64979(14) 0.08958(8) 0.0101(2) Uani 1 1 d . . .
C12 C -0.36716(17) -0.67973(14) 0.06119(8) 0.0121(2) Uani 1 1 d . . .
C13 C -0.19328(18) -0.54172(15) 0.09634(9) 0.0131(2) Uani 1 1 d . . .
C14 C -0.74212(17) -0.79458(14) 0.05255(8) 0.0109(2) Uani 1 1 d . . .
D1 D 0.453(4) 0.225(3) 0.3284(16) 0.056(6) Uiso 1 1 d . . .
H2 H 0.857(2) 0.230(2) 0.2708(12) 0.019(4) Uiso 1 1 d . . .
H3 H 1.168(3) 0.452(2) 0.3266(12) 0.022(4) Uiso 1 1 d . . .
H4 H 0.857(2) 0.786(2) 0.4836(12) 0.022(4) Uiso 1 1 d . . .
H5 H 0.564(2) 0.551(2) 0.4236(11) 0.017(4) Uiso 1 1 d . . .
D6 D 1.384(3) 1.024(3) 0.5604(14) 0.041(5) Uiso 1 1 d . . .
D7 D 1.152(3) 0.929(2) 0.5736(12) 0.020(4) Uiso 1 1 d . . .
D8 D -0.051(3) -0.285(3) 0.1732(15) 0.058(6) Uiso 1 1 d . . .
H9 H -0.362(3) -0.232(2) 0.2283(12) 0.021(4) Uiso 1 1 d . . .
H10 H -0.674(2) -0.453(2) 0.1752(11) 0.016(4) Uiso 1 1 d . . .
H11 H -0.357(2) -0.790(2) 0.0179(12) 0.019(4) Uiso 1 1 d . . .
H12 H -0.067(2) -0.5530(19) 0.0797(11) 0.015(4) Uiso 1 1 d . . .
D13 D -0.879(3) -1.018(2) -0.0634(12) 0.024(4) Uiso 1 1 d . . .
D14 D -0.638(3) -0.925(2) -0.0759(12) 0.023(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
O1 0.0115(4) 0.0136(4) 0.0177(4) -0.0026(3) 0.0050(3) -0.0005(3)
O2 0.0096(4) 0.0143(4) 0.0177(4) 0.0015(3) 0.0050(3) 0.0014(3)
O3 0.0094(4) 0.0148(4) 0.0172(4) 0.0006(3) 0.0062(3) 0.0014(3)
O4 0.0114(4) 0.0139(4) 0.0186(4) -0.0021(3) 0.0050(3) -0.0005(3)
O5 0.0108(4) 0.0168(4) 0.0178(4) 0.0004(3) 0.0055(3) 0.0017(3)
O6 0.0106(4) 0.0155(4) 0.0178(4) -0.0003(3) 0.0056(3) 0.0013(3)
N1 0.0117(5) 0.0122(4) 0.0132(4) 0.0027(3) 0.0009(3) 0.0018(3)
N2 0.0103(5) 0.0122(4) 0.0141(4) 0.0004(3) 0.0041(3) 0.0015(3)
N3 0.0101(5) 0.0118(4) 0.0136(4) 0.0029(3) 0.0005(3) 0.0005(3)
N4 0.0099(5) 0.0117(4) 0.0137(4) -0.0002(3) 0.0030(3) 0.0006(3)
C1 0.0103(5) 0.0125(5) 0.0123(4) 0.0032(4) 0.0033(4) 0.0036(4)
C2 0.0093(5) 0.0126(5) 0.0132(4) 0.0033(4) 0.0029(4) 0.0032(4)
C3 0.0128(6) 0.0115(5) 0.0138(5) 0.0027(4) 0.0025(4) 0.0029(4)
C4 0.0120(5) 0.0116(5) 0.0129(4) 0.0021(4) 0.0032(4) 0.0040(4)
C5 0.0090(5) 0.0107(4) 0.0108(4) 0.0024(4) 0.0014(3) 0.0021(4)
C6 0.0112(5) 0.0100(4) 0.0130(4) 0.0011(4) 0.0020(4) 0.0025(4)
C7 0.0099(5) 0.0129(5) 0.0148(5) 0.0028(4) 0.0019(4) 0.0025(4)
C8 0.0092(5) 0.0103(4) 0.0127(4) 0.0021(4) 0.0015(4) 0.0017(4)
C9 0.0130(6) 0.0115(5) 0.0144(5) 0.0027(4) 0.0009(4) 0.0021(4)
C10 0.0105(5) 0.0120(5) 0.0138(5) 0.0022(4) 0.0018(4) 0.0030(4)
C11 0.0089(5) 0.0105(4) 0.0100(4) 0.0027(4) 0.0010(3) 0.0017(4)
C12 0.0102(5) 0.0108(5) 0.0135(4) 0.0014(4) 0.0019(4) 0.0024(4)
C13 0.0087(5) 0.0138(5) 0.0152(5) 0.0036(4) 0.0020(4) 0.0018(4)
C14 0.0090(5) 0.0101(4) 0.0123(4) 0.0025(4) 0.0014(4) 0.0017(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3056(14) . ?
O1 D1 0.95(2) . ?
O2 C1 1.2181(14) . ?
O3 C2 1.2463(14) . ?
O4 C2 1.2506(14) . ?
O5 C8 1.2387(13) . ?
O6 C14 1.2399(13) . ?
N1 C7 1.3381(14) . ?
N1 C3 1.3433(15) . ?
N2 D7 0.875(17) . ?
N2 D6 1.02(2) . ?
N2 C8 1.3341(13) . ?
N3 C9 1.3392(15) . ?
N3 C13 1.3407(14) . ?
N3 D8 1.08(2) . ?
N4 D14 0.954(17) . ?
N4 D13 0.978(18) . ?
N4 C14 1.3313(13) . ?
C1 C2 1.5490(15) . ?
C3 H2 0.961(15) . ?
C3 C4 1.3843(16) . ?
C4 H3 0.978(17) . ?
C4 C5 1.3907(14) . ?
C5 C6 1.3882(16) . ?
C5 C8 1.5027(15) . ?
C6 H4 0.929(15) . ?
C6 C7 1.3835(16) . ?
C7 H5 0.966(16) . ?
C9 H9 0.938(16) . ?
C9 C10 1.3830(16) . ?
C10 H10 0.998(15) . ?
C10 C11 1.3918(14) . ?
C11 C12 1.3881(16) . ?
C11 C14 1.5034(15) . ?
C12 H11 0.944(15) . ?
C12 C13 1.3776(16) . ?
C13 H12 0.937(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
C1 O1 D1 116.9(12) . . ?
C7 N1 C3 117.65(10) . . ?
D7 N2 D6 120.0(14) . . ?
D7 N2 C8 122.1(11) . . ?
D6 N2 C8 117.4(10) . . ?
C9 N3 C13 122.12(10) . . ?
C9 N3 D8 126.7(11) . . ?
C13 N3 D8 111.1(11) . . ?
D14 N4 D13 121.5(13) . . ?
D14 N4 C14 120.7(10) . . ?
D13 N4 C14 117.6(9) . . ?
O2 C1 O1 122.08(10) . . ?
O2 C1 C2 120.98(10) . . ?
O1 C1 C2 116.93(10) . . ?
O3 C2 O4 128.33(10) . . ?
O3 C2 C1 116.70(9) . . ?
O4 C2 C1 114.97(10) . . ?
H2 C3 N1 115.7(10) . . ?
H2 C3 C4 121.4(10) . . ?
N1 C3 C4 122.86(10) . . ?
H3 C4 C3 119.1(9) . . ?
H3 C4 C5 121.8(9) . . ?
C3 C4 C5 118.96(11) . . ?
C6 C5 C4 118.47(10) . . ?
C6 C5 C8 121.96(9) . . ?
C4 C5 C8 119.56(10) . . ?
H4 C6 C7 118.4(10) . . ?
H4 C6 C5 122.9(10) . . ?
C7 C6 C5 118.69(10) . . ?
H5 C7 N1 115.1(9) . . ?
H5 C7 C6 121.5(9) . . ?
N1 C7 C6 123.37(11) . . ?
O5 C8 N2 123.31(10) . . ?
O5 C8 C5 119.79(9) . . ?
N2 C8 C5 116.89(10) . . ?
H9 C9 N3 117.6(10) . . ?
H9 C9 C10 122.6(10) . . ?
N3 C9 C10 119.83(10) . . ?
H10 C10 C9 118.1(9) . . ?
H10 C10 C11 122.6(9) . . ?
C9 C10 C11 119.24(11) . . ?
C12 C11 C10 119.42(10) . . ?
C12 C11 C14 121.47(9) . . ?
C10 C11 C14 119.11(10) . . ?
H11 C12 C13 117.5(10) . . ?
H11 C12 C11 123.4(10) . . ?
C13 C12 C11 119.05(10) . . ?
H12 C13 N3 116.4(9) . . ?
H12 C13 C12 123.3(9) . . ?
N3 C13 C12 120.33(11) . . ?
O6 C14 N4 124.02(10) . . ?
O6 C14 C11 119.03(9) . . ?
N4 C14 C11 116.94(10) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        34.11
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.070
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: D2O'
