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In the crystal structure of the title compound, C6H10N3+·C7H5O3, the asymmetric unit contains four crystallographically independent 2-amino-4,6-dimethyl­pyrimidinium and salicylate ions (Z = 8). In each of these, one of the pyrimidine N atoms is protonated, and the carboxyl­ate group of the salicylate ion inter­acts with the pyrimidine group through a pair of N—H...O hydrogen bonds, forming an R22(8) motif. The pyrimidine cations also form base pairs via a pair of N—H...N hydrogen bonds (involving the amino group and the unprotonated ring N atom), forming another R22(8) motif. Three such R22(8) motifs, fused together, constitute a closed cyclic aggregate, and the linking of these aggregates, arranged in consecutive layers, can be analysed in terms of off-face stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106031015/gz3021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106031015/gz3021Isup2.hkl
Contains datablock I

CCDC reference: 288734

Comment top

The hydrogen-bonding patterns, including base-pairing, formed by aminopyrimidines, and base stacking, are important in nucleic acid structures and their functions. Some aminopyrimidine derivatives are used as antifolate drugs (Hunt et al., 1980; Baker & Santi, 1965). 2-Aminopyrimidine and its derivatives are of particular interest as adduct formers because of their ability to form stable hydrogen-bonded chains via their stereochemically associated amine group and the ring N atoms (Lynch et al., 2000; Lynch & Jones, 2004). Salicylic acid is a widely used analgesic. The crystal structures of aminopyrimidine derivatives (Schwalbe & Williams, 1982), aminopyrimidine carboxylates (Hu et al., 2002) and co-crystal structures (Chinnakali et al., 1999) have been reported. The crystal structure of 2-amino-4,6-dimethylpyrimidinium bromide 2-amino-4,6-dimethylpyrimidine monohydrate (Panneerselvam et al., 2004), 2-amino-4,6-dimethylpyrimidinium hydrogen sulfate (Hemamalini et al., 2005), bis(2,4-diamino-6-oxopyrimidinium) sulfate monohydrate (Muthiah et al., 2004) and 2-amino-4,6-dimethylpyrimidine–cinnamic acid (1/2) (Balasubramani et al., 2005) have recently been reported from our laboratory. The present study is aimed at investigating the supramolecular interactions of the title compound, (I).

The asymmetric unit of (I) consists of four crystallographically independent 2-amino-4,6-dimethylpyrimidinium cations and salicylate anions, as shown in Fig. 1. The constituent atoms of all four ionic pairs have been labelled in an identical manner, except that the individual molecules are identified by the suffix A, B, C or D. Protonation of the pyrimidine base on the N1 site is reflected in a change in bond angle compared with the unprotonated site (Panneerselvam et al., 2004). The average value of the valence angle at the unprotonated atom N3 for the four molecules in the asymmetric unit is 116.7 (5)°, and that at the protonated atom N1 120.1 (5)° (Table 1). The geometry of the pyrimidine cation agrees with that of other pyrimidine cations reported in the literature (Panneerselvam et al., 2004).

A view of the molecular packing is shown in Fig. 2. The constituents of each ionic pair (A, B, C or D) are bonded through a pair of N—H···O hydrogen bonds, forming an eight-membered hydrogen-bonded ring motif with graph-set R22(8) (Bernstein et al., 1995). The independent ionic pairs pack in pairs (A and B, and C and D). Pairs of hydrogen bonds involving the 2-amino group and the pyrimidine atom N3 link cation A to cation B (N2B—H2B1···N3A and N3B···H2A2—N2A) and cation C to cation D (N2D—H2D1···N3C and N3D···H2C1—N2C), to form an R22(8) ring motif. The typical intramolecular hydrogen bond between the phenolic –OH and the carboxylate group is also present in all the salicylate moieties (Panneerselvam et al.,2002). Hence, the eight-component asymmetric unit can be considered as being composed of two closed cyclic aggregates, each consisting of two 2-amino-4,6-dimethylpyrimidinium cations and two salicylate anions, together forming the R86(28) hydrogen-bond pattern. Within each aggregate, the pyrimidine cations are inclined to each other at 18.2 (3) and 17.5 (2)°, and the salicylate anions at 23.2 (3) and 25.6 (3)°. The aggregates formed by molecules A and B, and those formed by molecules C and D, lie on two adjacent parallel planes.

These aggregates are inclined to each other at an angle of 13.2 (2)°, and are linked by off-face ππ interactions. The 2-amino-4,6-dimethylpyrimidinium cation A forms stacking interactions with the aryl rings of the salicylate anions of molecules Ci and Dii, with perpendicular separations of 3.292 and 3.389 Å, respectively, centroid-to-centroid distances of 3.683 (3) and 3.681 (3) Å, respectively, and slip angles (the angle between the centroid vector and the normal to the plane) of 18.6 and 16.2°, respectively [symmetry codes: (i) −x, 1/2 + y, −z; (ii) x, y, −1 + z Please check symmetry codes have been added correctly in above text]. A similar type of stacking is also observed between the 2-amino-4,6-dimethylpyrimidinium cations of molecules Ci and Diii and salicylate anion A, with perpendicular separations of 3.295 and 3.434 Å, respectively, centroid-to-centroid distances of 3.725 (3) and 3.751 (3) Å, respectively, and slip angles of 20.27 and 19.91°, respectively (Fig. 3) [symmetry code: (iii) x, y, 1 + z Please check symmetry code has been added correctly in above text]. These are all typical aromatic stacking values (Hunter, 1994).

Experimental top

A hot methanol solution (20 ml) of 2-amino-4,6-dimethylpyrimidine (31 mg; Aldrich) and a methanol solution (20 ml) of salicylic acid (45 mg; LOBA Chemie, India) were mixed in a 1:1 molar ratio and warmed for 30 min over a water bath. On slow evaporation of the resulting mixture, prismatic colourless crystals of (I) were obtained.

Refinement top

In the absence of significant anomalous scattering effects, Friedel pairs were averaged. All H atoms were located in difference Fourier maps and were then relocated in idealized positions and refined as riding on their carrier atoms, with N—H = 0.85–0.86 Å, O—H = 0.82 Å and C—H = 0.95–0.96 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2000); cell refinement: CrysAlis RED (Oxford Diffraction, 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. A molecular drawing of the asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atom0numbering scheme. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A view of the hydrogen-bonding interactions in (I) (dashed lines). For clarity, H atoms not involved in hydrogen bonding have been omitted. [Symmetry codes: (i) ?; (ii) ?; (iii) ? Please complete]
[Figure 3] Fig. 3. A view of ππ stacking interactions in compound (I). H atoms have been omitted.
2-amino-4,6-dimethylpyrimidinium salicylate top
Crystal data top
C6H10N3+·C7H5O3F(000) = 1104
Mr = 261.28Dx = 1.310 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1961 reflections
a = 11.039 (2) Åθ = 4.1–25.0°
b = 13.995 (3) ŵ = 0.10 mm1
c = 17.371 (3) ÅT = 295 K
β = 99.04 (3)°Prismatic, colourless
V = 2650.3 (9) Å30.45 × 0.3 × 0.2 mm
Z = 8
Data collection top
Kuma KM-4 CCD κ-geometry
diffractometer
2229 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.082
Graphite monochromatorθmax = 25.0°, θmin = 4.1°
ω scansh = 1213
20586 measured reflectionsk = 1615
4865 independent reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 0.90 w = 1/[σ2(Fo2) + (0.0195P)2]
where P = (Fo2 + 2Fc2)/3
4865 reflections(Δ/σ)max = 0.001
698 parametersΔρmax = 0.14 e Å3
1 restraintΔρmin = 0.12 e Å3
Crystal data top
C6H10N3+·C7H5O3V = 2650.3 (9) Å3
Mr = 261.28Z = 8
Monoclinic, P21Mo Kα radiation
a = 11.039 (2) ŵ = 0.10 mm1
b = 13.995 (3) ÅT = 295 K
c = 17.371 (3) Å0.45 × 0.3 × 0.2 mm
β = 99.04 (3)°
Data collection top
Kuma KM-4 CCD κ-geometry
diffractometer
2229 reflections with I > 2σ(I)
20586 measured reflectionsRint = 0.082
4865 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.082H-atom parameters constrained
S = 0.90Δρmax = 0.14 e Å3
4865 reflectionsΔρmin = 0.12 e Å3
698 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.2136 (5)0.4842 (3)0.1467 (3)0.047 (2)
N2A0.0539 (4)0.4880 (4)0.0464 (3)0.063 (2)
N3A0.2474 (5)0.4729 (3)0.0155 (3)0.047 (2)
C2A0.1733 (7)0.4819 (5)0.0690 (4)0.052 (3)
C4A0.3672 (6)0.4633 (4)0.0451 (4)0.051 (3)
C5A0.4132 (6)0.4654 (4)0.1236 (3)0.054 (3)
C6A0.3320 (6)0.4771 (4)0.1738 (4)0.047 (2)
C7A0.4502 (5)0.4544 (4)0.0160 (4)0.072 (3)
C8A0.3675 (5)0.4836 (4)0.2606 (3)0.069 (3)
N1B0.0259 (4)0.5387 (3)0.2504 (3)0.050 (2)
N2B0.1422 (4)0.5282 (3)0.1538 (3)0.0601 (19)
N3B0.0486 (5)0.5026 (3)0.1203 (3)0.0435 (19)
C2B0.0216 (6)0.5224 (4)0.1738 (4)0.045 (3)
C4B0.1698 (6)0.4974 (4)0.1455 (4)0.052 (3)
C5B0.2215 (6)0.5126 (4)0.2231 (4)0.055 (3)
C6B0.1466 (6)0.5324 (4)0.2746 (3)0.047 (3)
C7B0.2469 (6)0.4747 (4)0.0835 (4)0.066 (3)
C8B0.1905 (5)0.5486 (4)0.3588 (3)0.072 (3)
N1C0.1462 (5)0.3273 (3)0.3361 (3)0.0475 (19)
N2C0.0205 (5)0.3252 (3)0.4361 (2)0.065 (2)
N3C0.1724 (5)0.3434 (4)0.4686 (3)0.051 (2)
C2C0.0998 (6)0.3322 (4)0.4137 (4)0.048 (2)
C4C0.2884 (7)0.3523 (4)0.4448 (4)0.052 (3)
C5C0.3404 (6)0.3488 (4)0.3668 (4)0.054 (3)
C6C0.2668 (6)0.3366 (4)0.3121 (4)0.044 (2)
C7C0.3705 (6)0.3648 (5)0.5058 (4)0.075 (3)
C8C0.3081 (5)0.3292 (4)0.2253 (3)0.069 (3)
N1D0.0936 (5)0.2996 (3)0.7365 (3)0.0449 (19)
N2D0.0711 (4)0.3039 (3)0.6374 (3)0.061 (2)
N3D0.1229 (5)0.3287 (4)0.6069 (3)0.049 (2)
C2D0.0502 (6)0.3115 (4)0.6607 (4)0.042 (2)
C4D0.2403 (7)0.3332 (4)0.6301 (4)0.046 (3)
C5D0.2924 (5)0.3228 (4)0.7087 (4)0.055 (3)
C6D0.2167 (6)0.3067 (4)0.7614 (4)0.055 (3)
C7D0.3224 (5)0.3545 (4)0.5719 (3)0.064 (3)
C8D0.2558 (5)0.2926 (5)0.8483 (3)0.073 (3)
O1A0.3025 (4)0.5705 (4)0.1988 (3)0.0761 (19)
O2A0.1013 (4)0.5212 (3)0.1600 (2)0.0672 (17)
O3A0.0695 (4)0.5162 (3)0.2486 (2)0.0718 (19)
C9A0.0445 (7)0.5305 (5)0.2292 (4)0.058 (3)
C10A0.1181 (6)0.5552 (4)0.2901 (4)0.048 (3)
C11A0.0623 (6)0.5627 (4)0.3689 (4)0.059 (3)
C12A0.1266 (7)0.5869 (5)0.4254 (4)0.068 (3)
C13A0.2511 (7)0.6052 (4)0.4067 (5)0.065 (3)
C14A0.3089 (6)0.5983 (5)0.3305 (5)0.067 (3)
C15A0.2409 (7)0.5755 (4)0.2737 (4)0.048 (3)
O1B0.4887 (4)0.5875 (4)0.3302 (2)0.0838 (19)
O2B0.2867 (4)0.5688 (3)0.2748 (2)0.0616 (17)
O3B0.1092 (4)0.5734 (3)0.3556 (2)0.0639 (19)
C9B0.2248 (7)0.5779 (4)0.3421 (4)0.049 (3)
C10B0.2923 (6)0.5964 (4)0.4093 (4)0.040 (2)
C11B0.2261 (6)0.6085 (4)0.4841 (4)0.056 (3)
C12B0.2836 (6)0.6242 (4)0.5471 (3)0.059 (3)
C13B0.4101 (6)0.6276 (4)0.5360 (4)0.062 (3)
C14B0.4775 (6)0.6153 (4)0.4629 (4)0.067 (3)
C15B0.4174 (6)0.5985 (4)0.3998 (4)0.050 (3)
O1C0.3686 (4)0.2529 (4)0.2766 (2)0.0837 (19)
O2C0.1668 (3)0.2918 (3)0.3185 (2)0.0616 (18)
O3C0.0057 (4)0.2945 (3)0.2321 (2)0.0656 (19)
C9C0.1072 (7)0.2831 (5)0.2495 (4)0.052 (3)
C10C0.1815 (6)0.2549 (4)0.1882 (3)0.042 (3)
C11C0.1228 (6)0.2426 (5)0.1130 (4)0.058 (3)
C12C0.1875 (7)0.2199 (5)0.0530 (4)0.069 (3)
C13C0.3085 (7)0.2061 (4)0.0693 (4)0.059 (3)
C14C0.3710 (6)0.2170 (4)0.1424 (4)0.061 (3)
C15C0.3081 (6)0.2417 (4)0.2032 (4)0.054 (3)
O1D0.4222 (4)0.2271 (4)0.8055 (2)0.0740 (19)
O2D0.2195 (4)0.2619 (3)0.7557 (2)0.0604 (16)
O3D0.0437 (4)0.2610 (3)0.8391 (2)0.0759 (19)
C9D0.1581 (7)0.2550 (4)0.8237 (4)0.053 (3)
C10D0.2256 (5)0.2375 (4)0.8901 (4)0.039 (2)
C11D0.1642 (5)0.2301 (4)0.9651 (3)0.052 (3)
C12D0.2259 (6)0.2116 (5)1.0278 (4)0.068 (3)
C13D0.3507 (7)0.1990 (5)1.0143 (4)0.065 (3)
C14D0.4139 (6)0.2029 (4)0.9405 (4)0.055 (3)
C15D0.3534 (6)0.2238 (4)0.8785 (4)0.053 (3)
H1A0.162000.490600.178600.0570*
H5A0.496700.459000.141500.0640*
H2A10.024000.486300.002400.0760*
H2A20.005800.493700.080600.0760*
H8A10.324400.535600.280100.1030*
H8A20.454300.494500.272800.1030*
H8A30.347300.425000.284500.1030*
H7A10.523400.420300.005400.1080*
H7A20.472000.517000.032100.1080*
H7A30.408400.420100.060400.1080*
H2B10.176300.519100.106300.0720*
H1B0.022400.552900.283000.0590*
H2B20.186600.541000.188900.0720*
H8B10.201000.615800.368500.1080*
H8B20.267600.516600.373500.1080*
H8B30.131600.523700.388700.1080*
H5B0.305800.507500.238600.0660*
H7B10.199900.437900.042600.0980*
H7B20.316900.438300.106800.0980*
H7B30.273900.532700.062100.0980*
H1C0.097800.318200.302500.0570*
H5C0.424900.354200.352200.0650*
H2C10.068700.317000.402200.0780*
H2C20.050200.328500.484800.0780*
H8C10.248800.359800.198700.1030*
H8C20.386200.360000.211600.1030*
H8C30.315300.263200.210400.1030*
H7C10.341700.324300.549600.1120*
H7C20.453200.347400.484600.1120*
H7C30.368400.430200.522600.1120*
H1D0.044700.288100.769300.0540*
H5D0.376800.326700.724000.0660*
H2D10.119400.292300.670600.0730*
H2D20.100500.311200.588900.0730*
H8D10.223600.343800.875900.1100*
H8D20.343700.292300.860600.1100*
H8D30.224200.232800.863600.1100*
H7D10.308100.308200.530600.0970*
H7D20.406600.351600.596200.0970*
H7D30.304500.417300.550800.0970*
H11A0.021300.550900.381900.0710*
H12A0.087700.591200.476800.0810*
H13A0.295600.621500.446000.0780*
H14A0.392500.610800.318200.0800*
H1A10.262900.538400.172000.1140*
H11B0.140800.605800.491300.0680*
H12B0.237900.631500.596500.0700*
H13B0.449300.638800.578700.0740*
H14B0.562700.618000.456100.0800*
H1B10.446800.590100.295300.1250*
H11C0.038000.249800.102300.0700*
H12C0.146900.214600.002000.0820*
H13C0.351500.188100.029600.0710*
H14C0.455600.208500.152300.0730*
H1C10.318700.258500.306700.1250*
H11D0.079600.238300.974400.0630*
H12D0.182900.206801.078200.0810*
H13D0.392900.187601.055700.0780*
H14D0.498100.192100.931700.0660*
H1D10.380900.248900.774300.1110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.041 (4)0.060 (4)0.043 (4)0.002 (3)0.014 (3)0.002 (3)
N2A0.050 (4)0.102 (5)0.038 (3)0.002 (3)0.009 (3)0.003 (3)
N3A0.044 (4)0.063 (4)0.041 (3)0.005 (3)0.025 (3)0.003 (3)
C2A0.059 (5)0.050 (4)0.046 (5)0.002 (4)0.007 (4)0.003 (4)
C4A0.039 (5)0.047 (4)0.074 (5)0.004 (3)0.030 (4)0.007 (4)
C5A0.054 (5)0.065 (4)0.042 (4)0.001 (4)0.007 (4)0.001 (3)
C6A0.047 (4)0.049 (4)0.046 (4)0.008 (4)0.008 (4)0.001 (3)
C7A0.075 (5)0.061 (5)0.085 (5)0.012 (4)0.027 (4)0.005 (4)
C8A0.059 (4)0.076 (5)0.066 (5)0.008 (4)0.005 (4)0.007 (4)
N1B0.047 (4)0.059 (4)0.048 (4)0.002 (3)0.023 (3)0.007 (3)
N2B0.046 (3)0.092 (4)0.042 (3)0.008 (3)0.006 (3)0.013 (3)
N3B0.048 (4)0.052 (3)0.037 (3)0.005 (3)0.027 (3)0.006 (3)
C2B0.051 (5)0.047 (4)0.035 (4)0.012 (4)0.003 (4)0.002 (3)
C4B0.046 (5)0.056 (5)0.063 (5)0.004 (4)0.034 (4)0.002 (4)
C5B0.037 (4)0.071 (5)0.060 (5)0.001 (4)0.019 (4)0.001 (4)
C6B0.052 (5)0.049 (4)0.040 (4)0.001 (4)0.007 (4)0.005 (3)
C7B0.076 (5)0.058 (5)0.071 (5)0.011 (4)0.035 (4)0.006 (4)
C8B0.063 (5)0.095 (6)0.052 (4)0.004 (4)0.005 (4)0.006 (4)
N1C0.058 (4)0.053 (3)0.033 (3)0.003 (3)0.012 (3)0.004 (3)
N2C0.062 (4)0.103 (4)0.033 (3)0.005 (3)0.016 (3)0.001 (3)
N3C0.052 (4)0.064 (4)0.039 (3)0.001 (3)0.015 (3)0.007 (3)
C2C0.034 (4)0.060 (4)0.049 (4)0.003 (4)0.008 (4)0.003 (4)
C4C0.074 (6)0.031 (4)0.051 (5)0.006 (4)0.014 (4)0.015 (3)
C5C0.031 (4)0.064 (5)0.071 (5)0.001 (4)0.016 (4)0.001 (4)
C6C0.038 (4)0.038 (4)0.057 (4)0.011 (3)0.006 (4)0.002 (3)
C7C0.069 (5)0.090 (6)0.076 (5)0.017 (4)0.044 (5)0.006 (4)
C8C0.079 (5)0.081 (5)0.040 (4)0.008 (4)0.009 (3)0.009 (3)
N1D0.061 (4)0.048 (3)0.029 (3)0.003 (3)0.017 (3)0.011 (2)
N2D0.045 (4)0.108 (5)0.032 (3)0.002 (3)0.016 (3)0.009 (3)
N3D0.046 (4)0.056 (4)0.047 (3)0.004 (3)0.013 (3)0.002 (3)
C2D0.038 (4)0.046 (4)0.043 (4)0.008 (3)0.014 (4)0.009 (3)
C4D0.066 (5)0.033 (4)0.043 (4)0.010 (4)0.024 (4)0.003 (3)
C5D0.037 (4)0.069 (5)0.064 (5)0.005 (4)0.019 (4)0.003 (4)
C6D0.047 (5)0.052 (4)0.062 (5)0.002 (4)0.002 (4)0.009 (4)
C7D0.064 (5)0.067 (5)0.070 (5)0.013 (4)0.037 (4)0.008 (4)
C8D0.059 (5)0.107 (6)0.050 (4)0.005 (4)0.004 (3)0.019 (4)
O1A0.063 (3)0.095 (4)0.067 (3)0.011 (3)0.000 (3)0.002 (3)
O2A0.066 (3)0.094 (3)0.041 (3)0.003 (3)0.007 (2)0.007 (3)
O3A0.058 (3)0.115 (4)0.044 (3)0.018 (3)0.013 (2)0.002 (3)
C9A0.060 (5)0.055 (5)0.059 (5)0.008 (4)0.013 (4)0.008 (4)
C10A0.044 (5)0.052 (4)0.050 (5)0.006 (4)0.012 (4)0.000 (4)
C11A0.072 (5)0.063 (5)0.043 (4)0.008 (4)0.009 (4)0.000 (4)
C12A0.081 (6)0.088 (5)0.040 (4)0.000 (5)0.028 (4)0.006 (4)
C13A0.066 (6)0.064 (5)0.078 (6)0.011 (4)0.052 (5)0.016 (4)
C14A0.048 (5)0.082 (6)0.074 (6)0.010 (4)0.020 (5)0.014 (5)
C15A0.062 (5)0.039 (4)0.047 (4)0.006 (4)0.021 (4)0.001 (3)
O1B0.057 (3)0.151 (4)0.043 (3)0.003 (3)0.007 (2)0.006 (3)
O2B0.066 (3)0.078 (3)0.042 (3)0.009 (3)0.012 (3)0.007 (3)
O3B0.036 (3)0.104 (4)0.054 (3)0.002 (3)0.014 (2)0.019 (3)
C9B0.057 (5)0.052 (4)0.042 (5)0.009 (4)0.018 (4)0.004 (4)
C10B0.042 (4)0.031 (4)0.044 (4)0.009 (3)0.002 (3)0.012 (3)
C11B0.061 (5)0.068 (5)0.042 (4)0.012 (4)0.014 (4)0.003 (4)
C12B0.058 (5)0.080 (5)0.038 (4)0.012 (4)0.008 (4)0.009 (4)
C13B0.058 (5)0.078 (5)0.057 (5)0.003 (4)0.030 (4)0.002 (4)
C14B0.050 (5)0.084 (5)0.069 (5)0.005 (4)0.017 (4)0.011 (4)
C15B0.038 (4)0.078 (5)0.037 (4)0.003 (4)0.014 (4)0.000 (4)
O1C0.057 (3)0.135 (4)0.059 (3)0.003 (3)0.009 (2)0.004 (3)
O2C0.058 (3)0.093 (4)0.036 (2)0.007 (3)0.014 (2)0.004 (3)
O3C0.045 (3)0.104 (4)0.050 (3)0.006 (3)0.014 (2)0.006 (3)
C9C0.066 (5)0.060 (5)0.036 (4)0.011 (4)0.024 (4)0.006 (4)
C10C0.046 (5)0.051 (4)0.029 (4)0.004 (3)0.008 (3)0.003 (3)
C11C0.033 (4)0.082 (5)0.065 (5)0.001 (4)0.028 (4)0.002 (4)
C12C0.052 (5)0.098 (6)0.057 (5)0.011 (4)0.010 (4)0.012 (4)
C13C0.079 (6)0.056 (4)0.044 (4)0.002 (4)0.018 (4)0.010 (4)
C14C0.049 (5)0.056 (5)0.087 (6)0.001 (4)0.039 (4)0.008 (4)
C15C0.044 (5)0.057 (5)0.059 (5)0.001 (4)0.000 (4)0.011 (4)
O1D0.060 (3)0.102 (4)0.058 (3)0.007 (3)0.003 (3)0.001 (3)
O2D0.062 (3)0.087 (3)0.034 (2)0.007 (3)0.013 (2)0.010 (2)
O3D0.054 (3)0.125 (4)0.053 (3)0.000 (3)0.022 (3)0.006 (3)
C9D0.074 (6)0.050 (4)0.041 (4)0.019 (4)0.027 (4)0.015 (4)
C10D0.029 (4)0.052 (4)0.040 (4)0.003 (3)0.017 (3)0.007 (3)
C11D0.045 (4)0.073 (5)0.039 (4)0.003 (3)0.007 (3)0.013 (3)
C12D0.072 (6)0.091 (5)0.042 (4)0.007 (5)0.013 (4)0.010 (4)
C13D0.056 (5)0.093 (5)0.049 (5)0.014 (4)0.019 (4)0.001 (4)
C14D0.046 (5)0.069 (5)0.052 (5)0.000 (4)0.014 (4)0.000 (4)
C15D0.061 (5)0.055 (5)0.042 (4)0.017 (4)0.004 (4)0.009 (4)
Geometric parameters (Å, º) top
O1A—C15A1.372 (9)C8B—H8B20.9601
O2A—C9A1.272 (8)C8B—H8B30.9592
O3A—C9A1.267 (9)C4C—C5C1.387 (10)
O1A—H1A10.8207C4C—C7C1.509 (10)
N1A—C6A1.322 (9)C5C—C6C1.355 (10)
N1A—C2A1.354 (9)C6C—C8C1.509 (9)
O1B—C15B1.344 (8)C5C—H5C0.9305
N2A—C2A1.318 (9)C7C—H7C20.9606
O2B—C9B1.264 (8)C7C—H7C10.9619
N3A—C2A1.337 (9)C7C—H7C30.9598
N3A—C4A1.348 (9)C8C—H8C20.9598
O3B—C9B1.262 (9)C8C—H8C10.9594
N1A—H1A0.8595C8C—H8C30.9592
O1B—H1B10.8191C4D—C5D1.403 (10)
N2A—H2A20.8604C4D—C7D1.490 (9)
N2A—H2A10.8603C5D—C6D1.352 (9)
N1B—C6B1.336 (8)C6D—C8D1.516 (9)
N1B—C2B1.371 (9)C5D—H5D0.9294
O1C—C15C1.352 (8)C7D—H7D10.9612
N2B—C2B1.325 (8)C7D—H7D20.9594
O2C—C9C1.279 (8)C7D—H7D30.9608
N3B—C4B1.343 (9)C8D—H8D10.9608
N3B—C2B1.329 (9)C8D—H8D20.9602
O3C—C9C1.246 (9)C8D—H8D30.9601
N1B—H1B0.8599C9A—C10A1.473 (10)
O1C—H1C10.8207C10A—C15A1.370 (10)
N2B—H2B10.8609C10A—C11A1.414 (10)
N2B—H2B20.8591C11A—C12A1.342 (10)
N1C—C6C1.337 (9)C12A—C13A1.386 (11)
N1C—C2C1.366 (9)C13A—C14A1.380 (12)
O1D—C15D1.373 (8)C14A—C15A1.368 (11)
N2C—C2C1.327 (9)C11A—H11A0.9298
O2D—C9D1.270 (8)C12A—H12A0.9299
N3C—C4C1.288 (9)C13A—H13A0.9299
N3C—C2C1.348 (9)C14A—H14A0.9306
O3D—C9D1.252 (9)C9B—C10B1.503 (10)
N1C—H1C0.8604C10B—C11B1.397 (10)
O1D—H1D10.8200C10B—C15B1.365 (10)
N2C—H2C20.8591C11B—C12B1.366 (9)
N2C—H2C10.8611C12B—C13B1.380 (9)
N1D—C2D1.339 (9)C13B—C14B1.378 (10)
N1D—C6D1.363 (9)C14B—C15B1.388 (10)
N2D—C2D1.341 (8)C11B—H11B0.9310
N3D—C2D1.346 (9)C12B—H12B0.9302
N3D—C4D1.297 (10)C13B—H13B0.9289
N1D—H1D0.8594C14B—H14B0.9301
N2D—H2D10.8602C9C—C10C1.496 (9)
N2D—H2D20.8600C10C—C15C1.393 (9)
C4A—C7A1.512 (9)C10C—C11C1.375 (9)
C4A—C5A1.379 (9)C11C—C12C1.390 (10)
C5A—C6A1.355 (9)C12C—C13C1.335 (11)
C6A—C8A1.500 (9)C13C—C14C1.355 (10)
C5A—H5A0.9297C14C—C15C1.396 (10)
C7A—H7A30.9625C11C—H11C0.9308
C7A—H7A20.9617C12C—H12C0.9308
C7A—H7A10.9615C13C—H13C0.9313
C8A—H8A10.9599C14C—H14C0.9303
C8A—H8A30.9611C9D—C10D1.489 (10)
C8A—H8A20.9605C10D—C15D1.407 (9)
C4B—C5B1.395 (10)C10D—C11D1.375 (9)
C4B—C7B1.508 (10)C11D—C12D1.397 (9)
C5B—C6B1.339 (9)C12D—C13D1.372 (10)
C6B—C8B1.484 (7)C13D—C14D1.361 (10)
C5B—H5B0.9300C14D—C15D1.385 (10)
C7B—H7B10.9609C11D—H11D0.9295
C7B—H7B30.9595C12D—H12D0.9304
C7B—H7B20.9603C13D—H13D0.9300
C8B—H8B10.9593C14D—H14D0.9303
O1A···O2A2.517 (6)C2D···H2C23.0648
O1B···O1Di3.100 (6)C4B···H2A13.0181
O1B···O2B2.577 (6)C4C···H2D23.0443
O1C···O2C2.510 (6)C4D···H2C23.0190
O1D···O1Bii3.100 (6)C9A···H1A12.4616
O1D···O2D2.569 (6)C9A···H1A2.6288
O2A···O1A2.517 (6)C9A···H2A22.7726
O2A···N2A2.847 (6)C9B···H2B22.8070
O2B···N2B2.888 (6)C9B···H1B2.6247
O2B···C6C3.314 (7)C9B···H1B12.4637
O2B···O1B2.577 (6)C9C···H1C2.6201
O2C···O1C2.510 (6)C9C···H1C12.4141
O2C···C12Biii3.416 (7)C9C···H2C12.7921
O2C···N2C2.835 (6)C9D···H1D2.6046
O2D···O1D2.569 (6)C9D···H1D12.4758
O2D···N2D2.883 (6)C9D···H2D12.8080
O3A···C8A3.295 (7)C11A···H11Bviii3.0947
O3A···C6A3.401 (8)C11B···H7C33.0776
O3A···N1A2.598 (7)C11B···H7D1iv2.9365
O3B···N1B2.580 (6)C11B···H11Aix3.0863
O3B···C8B3.318 (7)C11C···H11Dviii3.0169
O3B···C6B3.396 (8)C12A···H11Bviii3.0879
O3B···C2Div3.416 (7)C12B···H7D1iv2.9002
O3C···N1C2.600 (7)C12B···H7C32.8816
O3C···C2B3.343 (7)C12C···H11Dviii3.0593
O3C···C8C3.357 (7)C12C···H7B13.0606
O3D···N1D2.572 (7)C13A···H7D3viii2.8186
O3D···C8D3.314 (7)C13B···H7C32.8163
O1A···H8C3v2.7097C13B···H7D1iv3.0666
O1A···H5Avi2.7651C14A···H8A2vi3.0207
O1B···H5Bvii2.7923C14B···H7C32.9739
O1C···H5Cvi2.8267C14D···H8D2vii3.0798
O1D···H5Dvii2.8077C15A···H8C3v2.9155
O1D···H1B1ii2.8351H2B1···N3A2.2336
O2A···H1A2.9053H2B1···C2A3.0946
O2A···H8D1viii2.8480H1A···H8A12.3929
O2A···H1A11.8441H1A···H2A22.2250
O2A···H2A21.9901H1A···O3A1.7435
O2B···H1B2.9072H1A···O2A2.9053
O2B···H1B11.8807H1A···C9A2.6288
O2B···H2B22.0291H1B···H2B22.2481
O2C···H2C11.9763H1B···H8B32.3340
O2C···H1C11.7830H1B···C9B2.6247
O2C···H12Biii2.7322H1B···O3B1.7236
O2C···H1C2.9138H1B···O2B2.9072
O2D···H8A3ix2.7164H1C···H2C12.3190
O2D···H1D11.8689H1C···O2C2.9138
O2D···H2D12.0250H1C···H8C12.3290
O2D···H1D2.9120H1C···C9C2.6201
O3A···H11A2.5036H1C···O3C1.7407
O3A···H1A1.7435H1D···O2D2.9120
O3A···H2A22.9095H1D···C9D2.6046
O3A···H8A12.7941H1D···O3D1.7141
O3B···H11B2.4784H1D···H8D32.4877
O3B···H8B32.7203H1D···H2D12.2910
O3B···H1B1.7236H2B2···O2B2.0291
O3C···H1C1.7407H2B2···C9B2.8070
O3C···H11C2.4596H2B2···H1B2.2481
O3C···H8C12.8079H8B2···H14Bvi2.5956
O3D···H11D2.4647H8B2···H5B2.4486
O3D···H1D1.7141H8B3···O3B2.7203
N1A···C9Dviii3.321 (7)H8B3···H1B2.3340
N1A···C9A3.446 (9)H5A···H8A22.4502
N1A···O3A2.598 (7)H5A···H7A12.4877
N1B···C9B3.447 (9)H5A···O1Avii2.7651
N1B···O3B2.580 (6)H5B···H7B22.5066
N1C···O3C2.600 (7)H5B···H8B22.4486
N1C···C9C3.434 (9)H5B···O1Bvi2.7923
N1D···O3D2.572 (7)H5C···H7C22.3711
N1D···C9D3.424 (9)H5C···H8C22.5460
N1D···C9Aix3.346 (8)H5C···O1Cvii2.8267
N2A···O2A2.847 (6)H5D···H8D22.5037
N2A···N3B2.946 (7)H5D···H7D22.3211
N2B···O2B2.888 (6)H5D···O1Dvi2.8077
N2B···N3A3.086 (7)H7B1···H2A12.5521
N2C···N3D3.005 (6)H7B1···C12C3.0606
N2C···O2C2.835 (6)H7B2···H5B2.5066
N2D···O2D2.883 (6)H7B3···C10Div3.0541
N2D···N3C3.021 (7)H7B3···C15Div2.9501
N3A···N2B3.086 (7)H7B3···C13Div2.8723
N3A···C13Cv3.432 (7)H7B3···C12Div2.9543
N3B···N2A2.946 (7)H7B3···C11Div3.0236
N3C···N2D3.021 (7)H7B3···C14Div2.8436
N3D···C11Aix3.382 (8)H2D1···C9D2.8080
N3D···N2C3.005 (6)H2D1···O2D2.0250
N2B···H8C12.7993H2D1···H1D2.2910
N3A···H2B12.2336H2D2···C2C3.0588
N3B···H2A12.0912H2D2···C4C3.0443
N3C···H2D22.1631H2D2···N3C2.1631
N3D···H2C22.1466H8D1···O2Aix2.8480
C2A···C11Dviii3.572 (9)H11A···O3A2.5036
C2A···C12Cv3.348 (10)H11A···C11Bviii3.0863
C2A···C10Dviii3.523 (9)H11A···H11Bviii2.5038
C2A···C13Cv3.474 (9)H11B···O3B2.4784
C2B···O3C3.343 (7)H11B···C11Aix3.0947
C2C···C13Ax3.582 (9)H11B···C12Aix3.0879
C2C···C12Ax3.454 (9)H11B···H11Aix2.5038
C2D···O3Biii3.416 (7)H11B···H12Aix2.5044
C2D···C11Aix3.558 (8)H11C···O3C2.4596
C2D···C10Aix3.567 (8)H11C···C12Dviii3.0434
C4A···C13Cv3.497 (8)H11C···C11Dviii3.0111
C4B···C10Div3.489 (8)H11C···H11Dviii2.3960
C4B···C10C3.472 (8)H11C···H12Dviii2.4825
C4C···C13Ax3.557 (8)H11D···O3D2.4647
C4C···C10B3.470 (8)H8D2···H5D2.5037
C4D···C10Biii3.450 (8)H8D2···C14Dvi3.0798
C5A···C15Dviii3.444 (8)H8D2···H14Dvi2.4215
C5A···C14Cv3.574 (8)H12A···H11Bviii2.5044
C5B···C9Div3.533 (8)H12B···O2Civ2.7322
C5B···C9C3.507 (9)H12C···H11Dviii2.4930
C5C···C13Ax3.586 (8)H8D3···H1D2.4877
C5C···C9B3.502 (8)H13A···H14Bxi2.4854
C5C···C14Ax3.589 (9)H13C···H14Dxi2.5571
C5C···C10B3.565 (8)H7D1···C12Biii2.9002
C5D···C9Biii3.588 (8)H7D1···C11Biii2.9365
C6A···O3A3.401 (8)H7D1···C13Biii3.0666
C6A···C14Cv3.439 (8)H14A···H8A2vi2.3900
C6B···C9Div3.564 (8)H14B···H8B2vii2.5956
C6B···C9C3.534 (9)H14B···H13Axii2.4854
C6B···O2Div3.372 (7)H14C···H13Dxi2.5652
C6B···O3B3.396 (8)H14D···H8D2vii2.4215
C6C···C9B3.437 (8)H7D2···H5D2.3211
C6C···C14Ax3.389 (9)H7D3···C13Aix2.8186
C6C···O2B3.314 (7)H1B1···O1Di2.8351
C7B···C11C3.593 (9)H1B1···C9B2.4637
C8A···O3A3.295 (7)H1B1···O2B1.8807
C8B···O3B3.318 (7)H1D1···O2D1.8689
C8C···O3C3.357 (7)H1D1···C9D2.4758
C8D···O3D3.314 (7)H2A1···N3B2.0912
C9A···N1A3.446 (9)H2A1···C4B3.0181
C9A···N1Dviii3.346 (8)H2A1···C2B3.0160
C9B···C5Div3.588 (8)H2A1···H7B12.5521
C9B···C5C3.502 (8)H2A2···C9A2.7726
C9B···N1B3.447 (9)H2A2···H1A2.2250
C9B···C6C3.437 (8)H2A2···O2A1.9901
C9C···N1C3.434 (9)H2A2···O3A2.9095
C9C···C6B3.534 (9)H2C1···O2C1.9763
C9C···C5B3.507 (9)H2C1···C9C2.7921
C9D···N1D3.424 (9)H2C1···H1C2.3190
C9D···N1Aix3.321 (7)H2C2···C4D3.0190
C10A···C2Dviii3.567 (8)H2C2···N3D2.1466
C10B···C5C3.565 (8)H2C2···C2D3.0648
C10B···C4C3.470 (8)H8A1···O3A2.7941
C10B···C4Div3.450 (8)H8A1···H1A2.3929
C10C···C4B3.472 (8)H8A2···H14Avii2.3900
C10D···C2Aix3.523 (9)H8A2···H5A2.4502
C11A···C2Dviii3.558 (8)H8A2···C14Avii3.0207
C11A···N3Dviii3.382 (8)H8A3···O2Dviii2.7163
C11C···C7B3.593 (9)H7A1···H5A2.4877
C11D···C2Aix3.572 (9)H7A2···C14Di2.9614
C12A···C2Cv3.454 (9)H7A2···H14Di2.5641
C12B···O2Civ3.416 (7)H1A1···C9A2.4616
C12C···C2Ax3.348 (10)H1A1···O2A1.8441
C13A···C5Cv3.586 (8)H8C1···O3C2.8079
C13A···C2Cv3.582 (9)H8C1···H1C2.3290
C13A···C4Cv3.557 (8)H8C1···N2B2.7993
C13C···C4Ax3.497 (8)H8C2···H5C2.5460
C13C···C2Ax3.474 (9)H8C3···C15Ax2.9155
C13C···N3Ax3.432 (7)H8C3···O1Ax2.7097
C14A···C5Cv3.589 (9)H7C2···H5C2.3711
C14A···C6Cv3.389 (9)H7C3···C13B2.8163
C14C···C6Ax3.439 (8)H7C3···C11B3.0776
C14C···C5Ax3.574 (8)H7C3···C12B2.8816
C15D···C5Aix3.444 (8)H7C3···C14B2.9739
C2A···H2B13.0946H1C1···C9C2.4141
C2B···H2A13.0160H1C1···O2C1.7830
C2C···H2D23.0588
C15A—O1A—H1A1109.70N1D—C2D—N3D123.0 (6)
C2A—N1A—C6A120.3 (6)N3D—C4D—C7D118.9 (6)
C2A—N3A—C4A114.5 (6)C5D—C4D—C7D118.7 (6)
C2A—N1A—H1A119.88N3D—C4D—C5D122.3 (6)
C6A—N1A—H1A119.78C4D—C5D—C6D118.3 (6)
C15B—O1B—H1B1109.99N1D—C6D—C8D114.8 (5)
C2A—N2A—H2A1120.18N1D—C6D—C5D119.3 (6)
C2A—N2A—H2A2119.82C5D—C6D—C8D125.9 (6)
H2A1—N2A—H2A2120.00C6D—C5D—H5D120.98
C2B—N1B—C6B120.3 (5)C4D—C5D—H5D120.75
C2B—N3B—C4B116.3 (6)C4D—C7D—H7D3109.35
C6B—N1B—H1B119.94H7D2—C7D—H7D3109.48
C2B—N1B—H1B119.71C4D—C7D—H7D1109.00
C15C—O1C—H1C1109.29H7D1—C7D—H7D3109.40
H2B1—N2B—H2B2119.92C4D—C7D—H7D2110.09
C2B—N2B—H2B1120.83H7D1—C7D—H7D2109.51
C2B—N2B—H2B2119.25C6D—C8D—H8D3109.27
C2C—N1C—C6C120.2 (6)H8D2—C8D—H8D3109.45
C2C—N3C—C4C117.1 (6)H8D1—C8D—H8D3109.45
C6C—N1C—H1C119.78C6D—C8D—H8D2109.98
C2C—N1C—H1C120.01C6D—C8D—H8D1109.27
C15D—O1D—H1D1109.80H8D1—C8D—H8D2109.41
H2C1—N2C—H2C2119.96O2A—C9A—O3A123.8 (6)
C2C—N2C—H2C2119.61O3A—C9A—C10A118.9 (6)
C2C—N2C—H2C1120.43O2A—C9A—C10A117.2 (6)
C2D—N1D—C6D119.2 (6)C9A—C10A—C15A122.6 (6)
C2D—N3D—C4D118.0 (6)C11A—C10A—C15A116.9 (6)
C2D—N1D—H1D120.68C9A—C10A—C11A120.5 (6)
C6D—N1D—H1D120.12C10A—C11A—C12A121.8 (6)
C2D—N2D—H2D1120.49C11A—C12A—C13A119.6 (7)
C2D—N2D—H2D2119.44C12A—C13A—C14A120.3 (7)
H2D1—N2D—H2D2120.06C13A—C14A—C15A119.0 (7)
N1A—C2A—N3A123.7 (7)C10A—C15A—C14A122.4 (7)
N1A—C2A—N2A116.9 (6)O1A—C15A—C10A120.9 (6)
N2A—C2A—N3A119.4 (6)O1A—C15A—C14A116.7 (7)
C5A—C4A—C7A121.8 (6)C12A—C11A—H11A119.08
N3A—C4A—C7A114.0 (6)C10A—C11A—H11A119.13
N3A—C4A—C5A124.2 (6)C11A—C12A—H12A120.07
C4A—C5A—C6A117.5 (6)C13A—C12A—H12A120.30
N1A—C6A—C8A116.2 (6)C12A—C13A—H13A119.48
N1A—C6A—C5A119.8 (6)C14A—C13A—H13A120.23
C5A—C6A—C8A124.0 (6)C13A—C14A—H14A119.98
C4A—C5A—H5A121.37C15A—C14A—H14A121.00
C6A—C5A—H5A121.18O2B—C9B—O3B123.4 (6)
H7A2—C7A—H7A3109.37O2B—C9B—C10B118.3 (6)
C4A—C7A—H7A3109.66O3B—C9B—C10B118.3 (6)
H7A1—C7A—H7A2109.34C9B—C10B—C11B119.5 (6)
C4A—C7A—H7A1109.55C9B—C10B—C15B121.7 (6)
H7A1—C7A—H7A3109.28C11B—C10B—C15B118.8 (6)
C4A—C7A—H7A2109.63C10B—C11B—C12B121.6 (6)
H8A1—C8A—H8A3109.45C11B—C12B—C13B118.7 (6)
C6A—C8A—H8A2108.99C12B—C13B—C14B120.8 (6)
H8A2—C8A—H8A3109.35C13B—C14B—C15B119.5 (6)
H8A1—C8A—H8A2109.53C10B—C15B—C14B120.6 (6)
C6A—C8A—H8A3109.92O1B—C15B—C10B123.0 (6)
C6A—C8A—H8A1109.57O1B—C15B—C14B116.4 (6)
N1B—C2B—N2B117.4 (6)C12B—C11B—H11B119.09
N2B—C2B—N3B120.1 (6)C10B—C11B—H11B119.35
N1B—C2B—N3B122.5 (6)C11B—C12B—H12B120.24
N3B—C4B—C7B115.1 (6)C13B—C12B—H12B121.01
C5B—C4B—C7B122.1 (6)C12B—C13B—H13B118.84
N3B—C4B—C5B122.8 (6)C14B—C13B—H13B120.34
C4B—C5B—C6B118.4 (6)C15B—C14B—H14B120.40
N1B—C6B—C5B119.6 (5)C13B—C14B—H14B120.05
N1B—C6B—C8B117.1 (5)O3C—C9C—C10C120.0 (6)
C5B—C6B—C8B123.3 (6)O2C—C9C—O3C124.3 (6)
C6B—C5B—H5B121.15O2C—C9C—C10C115.7 (6)
C4B—C5B—H5B120.46C11C—C10C—C15C118.1 (6)
H7B1—C7B—H7B2109.42C9C—C10C—C11C118.7 (6)
H7B1—C7B—H7B3109.36C9C—C10C—C15C123.2 (5)
C4B—C7B—H7B3110.06C10C—C11C—C12C121.3 (6)
C4B—C7B—H7B1109.95C11C—C12C—C13C119.3 (6)
H7B2—C7B—H7B3109.49C12C—C13C—C14C121.8 (7)
C4B—C7B—H7B2108.53C13C—C14C—C15C119.8 (6)
H8B2—C8B—H8B3109.54C10C—C15C—C14C119.7 (6)
C6B—C8B—H8B2109.23O1C—C15C—C10C119.6 (6)
H8B1—C8B—H8B2109.45O1C—C15C—C14C120.8 (6)
C6B—C8B—H8B3109.51C12C—C11C—H11C119.62
C6B—C8B—H8B1109.55C10C—C11C—H11C119.03
H8B1—C8B—H8B3109.54C11C—C12C—H12C120.31
N1C—C2C—N3C122.1 (6)C13C—C12C—H12C120.42
N1C—C2C—N2C119.2 (6)C12C—C13C—H13C119.43
N2C—C2C—N3C118.7 (6)C14C—C13C—H13C118.73
N3C—C4C—C7C117.5 (6)C15C—C14C—H14C119.75
C5C—C4C—C7C119.2 (7)C13C—C14C—H14C120.49
N3C—C4C—C5C123.2 (7)O2D—C9D—C10D118.3 (6)
C4C—C5C—C6C119.2 (6)O3D—C9D—C10D117.2 (6)
N1C—C6C—C5C118.1 (6)O2D—C9D—O3D124.5 (6)
C5C—C6C—C8C126.1 (6)C9D—C10D—C15D121.6 (6)
N1C—C6C—C8C115.8 (6)C11D—C10D—C15D117.4 (6)
C6C—C5C—H5C120.34C9D—C10D—C11D121.0 (5)
C4C—C5C—H5C120.45C10D—C11D—C12D121.7 (5)
C4C—C7C—H7C2109.93C11D—C12D—C13D119.4 (6)
C4C—C7C—H7C3109.61C12D—C13D—C14D120.5 (7)
H7C1—C7C—H7C2109.27C13D—C14D—C15D120.2 (6)
C4C—C7C—H7C1109.08O1D—C15D—C14D117.5 (6)
H7C2—C7C—H7C3109.54C10D—C15D—C14D120.9 (6)
H7C1—C7C—H7C3109.40O1D—C15D—C10D121.6 (6)
C6C—C8C—H8C3109.57C10D—C11D—H11D119.19
H8C1—C8C—H8C3109.50C12D—C11D—H11D119.15
C6C—C8C—H8C1109.20C11D—C12D—H12D120.53
H8C1—C8C—H8C2109.54C13D—C12D—H12D120.11
C6C—C8C—H8C2109.61C12D—C13D—H13D120.09
H8C2—C8C—H8C3109.42C14D—C13D—H13D119.36
N2D—C2D—N3D118.7 (6)C13D—C14D—H14D119.96
N1D—C2D—N2D118.2 (6)C15D—C14D—H14D119.87
C2A—N1A—C6A—C5A1.4 (8)C9A—C10A—C15A—C14A179.9 (6)
C2A—N1A—C6A—C8A178.1 (5)C11A—C10A—C15A—O1A179.7 (5)
C6A—N1A—C2A—N3A0.2 (9)C15A—C10A—C11A—C12A1.1 (9)
C6A—N1A—C2A—N2A179.1 (6)C11A—C10A—C15A—C14A2.6 (9)
C2A—N3A—C4A—C5A2.0 (8)C10A—C11A—C12A—C13A0.0 (10)
C4A—N3A—C2A—N1A1.9 (9)C11A—C12A—C13A—C14A0.2 (10)
C4A—N3A—C2A—N2A177.4 (6)C12A—C13A—C14A—C15A1.6 (10)
C2A—N3A—C4A—C7A179.3 (5)C13A—C14A—C15A—C10A2.9 (10)
C2B—N1B—C6B—C5B1.8 (8)C13A—C14A—C15A—O1A179.4 (6)
C6B—N1B—C2B—N2B178.9 (5)O3B—C9B—C10B—C11B0.3 (8)
C2B—N1B—C6B—C8B178.5 (5)O2B—C9B—C10B—C11B178.8 (5)
C6B—N1B—C2B—N3B1.9 (8)O2B—C9B—C10B—C15B3.5 (8)
C4B—N3B—C2B—N2B179.6 (5)O3B—C9B—C10B—C15B177.4 (5)
C2B—N3B—C4B—C5B0.6 (8)C11B—C10B—C15B—C14B2.0 (8)
C4B—N3B—C2B—N1B1.3 (8)C9B—C10B—C11B—C12B179.1 (5)
C2B—N3B—C4B—C7B179.9 (5)C15B—C10B—C11B—C12B1.3 (9)
C2C—N1C—C6C—C5C1.4 (8)C9B—C10B—C15B—O1B2.2 (9)
C6C—N1C—C2C—N3C2.1 (8)C9B—C10B—C15B—C14B179.7 (5)
C6C—N1C—C2C—N2C178.3 (5)C11B—C10B—C15B—O1B180.0 (6)
C2C—N1C—C6C—C8C179.5 (5)C10B—C11B—C12B—C13B0.3 (9)
C2C—N3C—C4C—C5C1.4 (9)C11B—C12B—C13B—C14B0.1 (8)
C4C—N3C—C2C—N2C178.4 (5)C12B—C13B—C14B—C15B0.5 (9)
C4C—N3C—C2C—N1C2.0 (9)C13B—C14B—C15B—C10B1.6 (9)
C2C—N3C—C4C—C7C180.0 (5)C13B—C14B—C15B—O1B179.8 (5)
C6D—N1D—C2D—N3D1.2 (8)O2C—C9C—C10C—C11C178.8 (6)
C2D—N1D—C6D—C8D179.6 (5)O3C—C9C—C10C—C11C0.4 (9)
C6D—N1D—C2D—N2D179.8 (5)O3C—C9C—C10C—C15C179.4 (6)
C2D—N1D—C6D—C5D1.9 (8)O2C—C9C—C10C—C15C2.1 (9)
C4D—N3D—C2D—N1D0.5 (9)C9C—C10C—C11C—C12C177.6 (6)
C2D—N3D—C4D—C7D178.5 (5)C11C—C10C—C15C—C14C0.2 (9)
C2D—N3D—C4D—C5D1.4 (9)C9C—C10C—C15C—O1C1.2 (9)
C4D—N3D—C2D—N2D178.1 (5)C9C—C10C—C15C—C14C178.9 (6)
C7A—C4A—C5A—C6A177.6 (5)C15C—C10C—C11C—C12C1.5 (10)
N3A—C4A—C5A—C6A0.6 (9)C11C—C10C—C15C—O1C179.8 (6)
C4A—C5A—C6A—N1A1.2 (8)C10C—C11C—C12C—C13C2.7 (10)
C4A—C5A—C6A—C8A178.2 (5)C11C—C12C—C13C—C14C2.4 (10)
C7B—C4B—C5B—C6B180.0 (5)C12C—C13C—C14C—C15C1.1 (9)
N3B—C4B—C5B—C6B0.6 (9)C13C—C14C—C15C—C10C0.0 (9)
C4B—C5B—C6B—C8B179.1 (5)C13C—C14C—C15C—O1C180.0 (6)
C4B—C5B—C6B—N1B1.2 (8)O2D—C9D—C10D—C15D3.3 (8)
N3C—C4C—C5C—C6C0.8 (9)O3D—C9D—C10D—C11D1.2 (8)
C7C—C4C—C5C—C6C179.3 (5)O2D—C9D—C10D—C11D179.5 (5)
C4C—C5C—C6C—C8C178.7 (5)O3D—C9D—C10D—C15D176.1 (5)
C4C—C5C—C6C—N1C0.8 (8)C15D—C10D—C11D—C12D1.2 (9)
C7D—C4D—C5D—C6D177.8 (5)C9D—C10D—C11D—C12D178.6 (6)
N3D—C4D—C5D—C6D0.6 (9)C11D—C10D—C15D—O1D178.1 (5)
C4D—C5D—C6D—C8D179.3 (6)C11D—C10D—C15D—C14D0.5 (8)
C4D—C5D—C6D—N1D1.1 (8)C9D—C10D—C15D—O1D0.8 (9)
O2A—C9A—C10A—C11A177.3 (6)C9D—C10D—C15D—C14D176.8 (5)
O2A—C9A—C10A—C15A5.3 (9)C10D—C11D—C12D—C13D1.0 (10)
O3A—C9A—C10A—C15A177.3 (6)C11D—C12D—C13D—C14D1.1 (10)
O3A—C9A—C10A—C11A0.1 (9)C12D—C13D—C14D—C15D2.8 (10)
C9A—C10A—C11A—C12A178.7 (6)C13D—C14D—C15D—C10D2.6 (9)
C9A—C10A—C15A—O1A2.2 (9)C13D—C14D—C15D—O1D179.7 (6)
Symmetry codes: (i) x1, y+1/2, z+1; (ii) x1, y1/2, z+1; (iii) x, y1/2, z+1; (iv) x, y+1/2, z+1; (v) x, y+1/2, z; (vi) x+1, y, z; (vii) x1, y, z; (viii) x, y, z1; (ix) x, y, z+1; (x) x, y1/2, z; (xi) x+1, y, z1; (xii) x1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2B—H2B1···N3A0.862.233.086 (7)171
N1A—H1A···O3A0.861.742.598 (7)172
N1B—H1B···O3B0.861.722.580 (6)174
N1C—H1C···O3C0.861.742.600 (7)177
N1D—H1D···O3D0.861.712.572 (7)176
N2B—H2B2···O2B0.862.032.888 (6)178
N2D—H2D1···O2D0.862.032.883 (6)175
N2D—H2D2···N3C0.862.163.021 (7)175
O1B—H1B1···O2B0.821.882.577 (6)142
O1D—H1D1···O2D0.821.872.569 (6)143
N2A—H2A1···N3B0.862.092.946 (7)172
N2A—H2A2···O2A0.861.992.847 (6)174
N2C—H2C1···O2C0.861.982.835 (6)175
N2C—H2C2···N3D0.862.153.005 (6)177
O1A—H1A1···O2A0.821.842.517 (6)138
O1C—H1C1···O2C0.821.782.510 (6)147
C11C—H11C···O3C0.932.462.782 (8)100

Experimental details

Crystal data
Chemical formulaC6H10N3+·C7H5O3
Mr261.28
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)11.039 (2), 13.995 (3), 17.371 (3)
β (°) 99.04 (3)
V3)2650.3 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.45 × 0.3 × 0.2
Data collection
DiffractometerKuma KM-4 CCD κ-geometry
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
20586, 4865, 2229
Rint0.082
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.082, 0.90
No. of reflections4865
No. of parameters698
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.12

Computer programs: CrysAlis CCD (Oxford Diffraction, 2000), CrysAlis RED (Oxford Diffraction, 2000), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.

Selected geometric parameters (Å, º) top
O1A—C15A1.372 (9)N3B—C4B1.343 (9)
O2A—C9A1.272 (8)N3B—C2B1.329 (9)
O3A—C9A1.267 (9)O3C—C9C1.246 (9)
N1A—C6A1.322 (9)N1C—C6C1.337 (9)
N1A—C2A1.354 (9)N1C—C2C1.366 (9)
O1B—C15B1.344 (8)O1D—C15D1.373 (8)
N2A—C2A1.318 (9)N2C—C2C1.327 (9)
O2B—C9B1.264 (8)O2D—C9D1.270 (8)
N3A—C2A1.337 (9)N3C—C4C1.288 (9)
N3A—C4A1.348 (9)N3C—C2C1.348 (9)
O3B—C9B1.262 (9)O3D—C9D1.252 (9)
N1B—C6B1.336 (8)N1D—C2D1.339 (9)
N1B—C2B1.371 (9)N1D—C6D1.363 (9)
O1C—C15C1.352 (8)N2D—C2D1.341 (8)
N2B—C2B1.325 (8)N3D—C2D1.346 (9)
O2C—C9C1.279 (8)N3D—C4D1.297 (10)
C2A—N1A—C6A120.3 (6)N1C—C6C—C8C115.8 (6)
C2A—N3A—C4A114.5 (6)N2D—C2D—N3D118.7 (6)
C2B—N1B—C6B120.3 (5)N1D—C2D—N2D118.2 (6)
C2B—N3B—C4B116.3 (6)N1D—C2D—N3D123.0 (6)
C2C—N1C—C6C120.2 (6)N3D—C4D—C7D118.9 (6)
C2C—N3C—C4C117.1 (6)N3D—C4D—C5D122.3 (6)
C2D—N1D—C6D119.2 (6)N1D—C6D—C8D114.8 (5)
C2D—N3D—C4D118.0 (6)N1D—C6D—C5D119.3 (6)
N1A—C2A—N3A123.7 (7)O2A—C9A—O3A123.8 (6)
N1A—C2A—N2A116.9 (6)O3A—C9A—C10A118.9 (6)
N2A—C2A—N3A119.4 (6)O2A—C9A—C10A117.2 (6)
N3A—C4A—C7A114.0 (6)O1A—C15A—C10A120.9 (6)
N3A—C4A—C5A124.2 (6)O1A—C15A—C14A116.7 (7)
N1A—C6A—C8A116.2 (6)O2B—C9B—O3B123.4 (6)
N1A—C6A—C5A119.8 (6)O2B—C9B—C10B118.3 (6)
N1B—C2B—N2B117.4 (6)O3B—C9B—C10B118.3 (6)
N2B—C2B—N3B120.1 (6)O1B—C15B—C10B123.0 (6)
N1B—C2B—N3B122.5 (6)O1B—C15B—C14B116.4 (6)
N3B—C4B—C7B115.1 (6)O3C—C9C—C10C120.0 (6)
N3B—C4B—C5B122.8 (6)O2C—C9C—O3C124.3 (6)
N1B—C6B—C5B119.6 (5)O2C—C9C—C10C115.7 (6)
N1B—C6B—C8B117.1 (5)O1C—C15C—C10C119.6 (6)
N1C—C2C—N3C122.1 (6)O1C—C15C—C14C120.8 (6)
N1C—C2C—N2C119.2 (6)O2D—C9D—C10D118.3 (6)
N2C—C2C—N3C118.7 (6)O3D—C9D—C10D117.2 (6)
N3C—C4C—C7C117.5 (6)O2D—C9D—O3D124.5 (6)
N3C—C4C—C5C123.2 (7)O1D—C15D—C14D117.5 (6)
N1C—C6C—C5C118.1 (6)O1D—C15D—C10D121.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2B—H2B1···N3A0.862.233.086 (7)171
N1A—H1A···O3A0.861.742.598 (7)172
N1B—H1B···O3B0.861.722.580 (6)174
N1C—H1C···O3C0.861.742.600 (7)177
N1D—H1D···O3D0.861.712.572 (7)176
N2B—H2B2···O2B0.862.032.888 (6)178
N2D—H2D1···O2D0.862.032.883 (6)175
N2D—H2D2···N3C0.862.163.021 (7)175
O1B—H1B1···O2B0.821.882.577 (6)142
O1D—H1D1···O2D0.821.872.569 (6)143
N2A—H2A1···N3B0.862.092.946 (7)172
N2A—H2A2···O2A0.861.992.847 (6)174
N2C—H2C1···O2C0.861.982.835 (6)175
N2C—H2C2···N3D0.862.153.005 (6)177
O1A—H1A1···O2A0.821.842.517 (6)138
O1C—H1C1···O2C0.821.782.510 (6)147
C11C—H11C···O3C0.932.462.782 (8)100
 

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