Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106031015/gz3021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106031015/gz3021Isup2.hkl |
CCDC reference: 288734
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.
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).
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.
C6H10N3+·C7H5O3− | F(000) = 1104 |
Mr = 261.28 | Dx = 1.310 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1961 reflections |
a = 11.039 (2) Å | θ = 4.1–25.0° |
b = 13.995 (3) Å | µ = 0.10 mm−1 |
c = 17.371 (3) Å | T = 295 K |
β = 99.04 (3)° | Prismatic, colourless |
V = 2650.3 (9) Å3 | 0.45 × 0.3 × 0.2 mm |
Z = 8 |
Kuma KM-4 CCD κ-geometry diffractometer | 2229 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.082 |
Graphite monochromator | θmax = 25.0°, θmin = 4.1° |
ω scans | h = −12→13 |
20586 measured reflections | k = −16→15 |
4865 independent reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-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 parameters | Δρmax = 0.14 e Å−3 |
1 restraint | Δρmin = −0.12 e Å−3 |
C6H10N3+·C7H5O3− | V = 2650.3 (9) Å3 |
Mr = 261.28 | Z = 8 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.039 (2) Å | µ = 0.10 mm−1 |
b = 13.995 (3) Å | T = 295 K |
c = 17.371 (3) Å | 0.45 × 0.3 × 0.2 mm |
β = 99.04 (3)° |
Kuma KM-4 CCD κ-geometry diffractometer | 2229 reflections with I > 2σ(I) |
20586 measured reflections | Rint = 0.082 |
4865 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 1 restraint |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.14 e Å−3 |
4865 reflections | Δρmin = −0.12 e Å−3 |
698 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | −0.2136 (5) | 0.4842 (3) | −0.1467 (3) | 0.047 (2) | |
N2A | −0.0539 (4) | 0.4880 (4) | −0.0464 (3) | 0.063 (2) | |
N3A | −0.2474 (5) | 0.4729 (3) | −0.0155 (3) | 0.047 (2) | |
C2A | −0.1733 (7) | 0.4819 (5) | −0.0690 (4) | 0.052 (3) | |
C4A | −0.3672 (6) | 0.4633 (4) | −0.0451 (4) | 0.051 (3) | |
C5A | −0.4132 (6) | 0.4654 (4) | −0.1236 (3) | 0.054 (3) | |
C6A | −0.3320 (6) | 0.4771 (4) | −0.1738 (4) | 0.047 (2) | |
C7A | −0.4502 (5) | 0.4544 (4) | 0.0160 (4) | 0.072 (3) | |
C8A | −0.3675 (5) | 0.4836 (4) | −0.2606 (3) | 0.069 (3) | |
N1B | 0.0259 (4) | 0.5387 (3) | 0.2504 (3) | 0.050 (2) | |
N2B | −0.1422 (4) | 0.5282 (3) | 0.1538 (3) | 0.0601 (19) | |
N3B | 0.0486 (5) | 0.5026 (3) | 0.1203 (3) | 0.0435 (19) | |
C2B | −0.0216 (6) | 0.5224 (4) | 0.1738 (4) | 0.045 (3) | |
C4B | 0.1698 (6) | 0.4974 (4) | 0.1455 (4) | 0.052 (3) | |
C5B | 0.2215 (6) | 0.5126 (4) | 0.2231 (4) | 0.055 (3) | |
C6B | 0.1466 (6) | 0.5324 (4) | 0.2746 (3) | 0.047 (3) | |
C7B | 0.2469 (6) | 0.4747 (4) | 0.0835 (4) | 0.066 (3) | |
C8B | 0.1905 (5) | 0.5486 (4) | 0.3588 (3) | 0.072 (3) | |
N1C | −0.1462 (5) | 0.3273 (3) | 0.3361 (3) | 0.0475 (19) | |
N2C | 0.0205 (5) | 0.3252 (3) | 0.4361 (2) | 0.065 (2) | |
N3C | −0.1724 (5) | 0.3434 (4) | 0.4686 (3) | 0.051 (2) | |
C2C | −0.0998 (6) | 0.3322 (4) | 0.4137 (4) | 0.048 (2) | |
C4C | −0.2884 (7) | 0.3523 (4) | 0.4448 (4) | 0.052 (3) | |
C5C | −0.3404 (6) | 0.3488 (4) | 0.3668 (4) | 0.054 (3) | |
C6C | −0.2668 (6) | 0.3366 (4) | 0.3121 (4) | 0.044 (2) | |
C7C | −0.3705 (6) | 0.3648 (5) | 0.5058 (4) | 0.075 (3) | |
C8C | −0.3081 (5) | 0.3292 (4) | 0.2253 (3) | 0.069 (3) | |
N1D | 0.0936 (5) | 0.2996 (3) | 0.7365 (3) | 0.0449 (19) | |
N2D | −0.0711 (4) | 0.3039 (3) | 0.6374 (3) | 0.061 (2) | |
N3D | 0.1229 (5) | 0.3287 (4) | 0.6069 (3) | 0.049 (2) | |
C2D | 0.0502 (6) | 0.3115 (4) | 0.6607 (4) | 0.042 (2) | |
C4D | 0.2403 (7) | 0.3332 (4) | 0.6301 (4) | 0.046 (3) | |
C5D | 0.2924 (5) | 0.3228 (4) | 0.7087 (4) | 0.055 (3) | |
C6D | 0.2167 (6) | 0.3067 (4) | 0.7614 (4) | 0.055 (3) | |
C7D | 0.3224 (5) | 0.3545 (4) | 0.5719 (3) | 0.064 (3) | |
C8D | 0.2558 (5) | 0.2926 (5) | 0.8483 (3) | 0.073 (3) | |
O1A | 0.3025 (4) | 0.5705 (4) | −0.1988 (3) | 0.0761 (19) | |
O2A | 0.1013 (4) | 0.5212 (3) | −0.1600 (2) | 0.0672 (17) | |
O3A | −0.0695 (4) | 0.5162 (3) | −0.2486 (2) | 0.0718 (19) | |
C9A | 0.0445 (7) | 0.5305 (5) | −0.2292 (4) | 0.058 (3) | |
C10A | 0.1181 (6) | 0.5552 (4) | −0.2901 (4) | 0.048 (3) | |
C11A | 0.0623 (6) | 0.5627 (4) | −0.3689 (4) | 0.059 (3) | |
C12A | 0.1266 (7) | 0.5869 (5) | −0.4254 (4) | 0.068 (3) | |
C13A | 0.2511 (7) | 0.6052 (4) | −0.4067 (5) | 0.065 (3) | |
C14A | 0.3089 (6) | 0.5983 (5) | −0.3305 (5) | 0.067 (3) | |
C15A | 0.2409 (7) | 0.5755 (4) | −0.2737 (4) | 0.048 (3) | |
O1B | −0.4887 (4) | 0.5875 (4) | 0.3302 (2) | 0.0838 (19) | |
O2B | −0.2867 (4) | 0.5688 (3) | 0.2748 (2) | 0.0616 (17) | |
O3B | −0.1092 (4) | 0.5734 (3) | 0.3556 (2) | 0.0639 (19) | |
C9B | −0.2248 (7) | 0.5779 (4) | 0.3421 (4) | 0.049 (3) | |
C10B | −0.2923 (6) | 0.5964 (4) | 0.4093 (4) | 0.040 (2) | |
C11B | −0.2261 (6) | 0.6085 (4) | 0.4841 (4) | 0.056 (3) | |
C12B | −0.2836 (6) | 0.6242 (4) | 0.5471 (3) | 0.059 (3) | |
C13B | −0.4101 (6) | 0.6276 (4) | 0.5360 (4) | 0.062 (3) | |
C14B | −0.4775 (6) | 0.6153 (4) | 0.4629 (4) | 0.067 (3) | |
C15B | −0.4174 (6) | 0.5985 (4) | 0.3998 (4) | 0.050 (3) | |
O1C | 0.3686 (4) | 0.2529 (4) | 0.2766 (2) | 0.0837 (19) | |
O2C | 0.1668 (3) | 0.2918 (3) | 0.3185 (2) | 0.0616 (18) | |
O3C | −0.0057 (4) | 0.2945 (3) | 0.2321 (2) | 0.0656 (19) | |
C9C | 0.1072 (7) | 0.2831 (5) | 0.2495 (4) | 0.052 (3) | |
C10C | 0.1815 (6) | 0.2549 (4) | 0.1882 (3) | 0.042 (3) | |
C11C | 0.1228 (6) | 0.2426 (5) | 0.1130 (4) | 0.058 (3) | |
C12C | 0.1875 (7) | 0.2199 (5) | 0.0530 (4) | 0.069 (3) | |
C13C | 0.3085 (7) | 0.2061 (4) | 0.0693 (4) | 0.059 (3) | |
C14C | 0.3710 (6) | 0.2170 (4) | 0.1424 (4) | 0.061 (3) | |
C15C | 0.3081 (6) | 0.2417 (4) | 0.2032 (4) | 0.054 (3) | |
O1D | −0.4222 (4) | 0.2271 (4) | 0.8055 (2) | 0.0740 (19) | |
O2D | −0.2195 (4) | 0.2619 (3) | 0.7557 (2) | 0.0604 (16) | |
O3D | −0.0437 (4) | 0.2610 (3) | 0.8391 (2) | 0.0759 (19) | |
C9D | −0.1581 (7) | 0.2550 (4) | 0.8237 (4) | 0.053 (3) | |
C10D | −0.2256 (5) | 0.2375 (4) | 0.8901 (4) | 0.039 (2) | |
C11D | −0.1642 (5) | 0.2301 (4) | 0.9651 (3) | 0.052 (3) | |
C12D | −0.2259 (6) | 0.2116 (5) | 1.0278 (4) | 0.068 (3) | |
C13D | −0.3507 (7) | 0.1990 (5) | 1.0143 (4) | 0.065 (3) | |
C14D | −0.4139 (6) | 0.2029 (4) | 0.9405 (4) | 0.055 (3) | |
C15D | −0.3534 (6) | 0.2238 (4) | 0.8785 (4) | 0.053 (3) | |
H1A | −0.16200 | 0.49060 | −0.17860 | 0.0570* | |
H5A | −0.49670 | 0.45900 | −0.14150 | 0.0640* | |
H2A1 | −0.02400 | 0.48630 | 0.00240 | 0.0760* | |
H2A2 | −0.00580 | 0.49370 | −0.08060 | 0.0760* | |
H8A1 | −0.32440 | 0.53560 | −0.28010 | 0.1030* | |
H8A2 | −0.45430 | 0.49450 | −0.27280 | 0.1030* | |
H8A3 | −0.34730 | 0.42500 | −0.28450 | 0.1030* | |
H7A1 | −0.52340 | 0.42030 | −0.00540 | 0.1080* | |
H7A2 | −0.47200 | 0.51700 | 0.03210 | 0.1080* | |
H7A3 | −0.40840 | 0.42010 | 0.06040 | 0.1080* | |
H2B1 | −0.17630 | 0.51910 | 0.10630 | 0.0720* | |
H1B | −0.02240 | 0.55290 | 0.28300 | 0.0590* | |
H2B2 | −0.18660 | 0.54100 | 0.18890 | 0.0720* | |
H8B1 | 0.20100 | 0.61580 | 0.36850 | 0.1080* | |
H8B2 | 0.26760 | 0.51660 | 0.37350 | 0.1080* | |
H8B3 | 0.13160 | 0.52370 | 0.38870 | 0.1080* | |
H5B | 0.30580 | 0.50750 | 0.23860 | 0.0660* | |
H7B1 | 0.19990 | 0.43790 | 0.04260 | 0.0980* | |
H7B2 | 0.31690 | 0.43830 | 0.10680 | 0.0980* | |
H7B3 | 0.27390 | 0.53270 | 0.06210 | 0.0980* | |
H1C | −0.09780 | 0.31820 | 0.30250 | 0.0570* | |
H5C | −0.42490 | 0.35420 | 0.35220 | 0.0650* | |
H2C1 | 0.06870 | 0.31700 | 0.40220 | 0.0780* | |
H2C2 | 0.05020 | 0.32850 | 0.48480 | 0.0780* | |
H8C1 | −0.24880 | 0.35980 | 0.19870 | 0.1030* | |
H8C2 | −0.38620 | 0.36000 | 0.21160 | 0.1030* | |
H8C3 | −0.31530 | 0.26320 | 0.21040 | 0.1030* | |
H7C1 | −0.34170 | 0.32430 | 0.54960 | 0.1120* | |
H7C2 | −0.45320 | 0.34740 | 0.48460 | 0.1120* | |
H7C3 | −0.36840 | 0.43020 | 0.52260 | 0.1120* | |
H1D | 0.04470 | 0.28810 | 0.76930 | 0.0540* | |
H5D | 0.37680 | 0.32670 | 0.72400 | 0.0660* | |
H2D1 | −0.11940 | 0.29230 | 0.67060 | 0.0730* | |
H2D2 | −0.10050 | 0.31120 | 0.58890 | 0.0730* | |
H8D1 | 0.22360 | 0.34380 | 0.87590 | 0.1100* | |
H8D2 | 0.34370 | 0.29230 | 0.86060 | 0.1100* | |
H8D3 | 0.22420 | 0.23280 | 0.86360 | 0.1100* | |
H7D1 | 0.30810 | 0.30820 | 0.53060 | 0.0970* | |
H7D2 | 0.40660 | 0.35160 | 0.59620 | 0.0970* | |
H7D3 | 0.30450 | 0.41730 | 0.55080 | 0.0970* | |
H11A | −0.02130 | 0.55090 | −0.38190 | 0.0710* | |
H12A | 0.08770 | 0.59120 | −0.47680 | 0.0810* | |
H13A | 0.29560 | 0.62150 | −0.44600 | 0.0780* | |
H14A | 0.39250 | 0.61080 | −0.31820 | 0.0800* | |
H1A1 | 0.26290 | 0.53840 | −0.17200 | 0.1140* | |
H11B | −0.14080 | 0.60580 | 0.49130 | 0.0680* | |
H12B | −0.23790 | 0.63150 | 0.59650 | 0.0700* | |
H13B | −0.44930 | 0.63880 | 0.57870 | 0.0740* | |
H14B | −0.56270 | 0.61800 | 0.45610 | 0.0800* | |
H1B1 | −0.44680 | 0.59010 | 0.29530 | 0.1250* | |
H11C | 0.03800 | 0.24980 | 0.10230 | 0.0700* | |
H12C | 0.14690 | 0.21460 | 0.00200 | 0.0820* | |
H13C | 0.35150 | 0.18810 | 0.02960 | 0.0710* | |
H14C | 0.45560 | 0.20850 | 0.15230 | 0.0730* | |
H1C1 | 0.31870 | 0.25850 | 0.30670 | 0.1250* | |
H11D | −0.07960 | 0.23830 | 0.97440 | 0.0630* | |
H12D | −0.18290 | 0.20680 | 1.07820 | 0.0810* | |
H13D | −0.39290 | 0.18760 | 1.05570 | 0.0780* | |
H14D | −0.49810 | 0.19210 | 0.93170 | 0.0660* | |
H1D1 | −0.38090 | 0.24890 | 0.77430 | 0.1110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.041 (4) | 0.060 (4) | 0.043 (4) | −0.002 (3) | 0.014 (3) | −0.002 (3) |
N2A | 0.050 (4) | 0.102 (5) | 0.038 (3) | −0.002 (3) | 0.009 (3) | 0.003 (3) |
N3A | 0.044 (4) | 0.063 (4) | 0.041 (3) | 0.005 (3) | 0.025 (3) | 0.003 (3) |
C2A | 0.059 (5) | 0.050 (4) | 0.046 (5) | 0.002 (4) | 0.007 (4) | 0.003 (4) |
C4A | 0.039 (5) | 0.047 (4) | 0.074 (5) | 0.004 (3) | 0.030 (4) | 0.007 (4) |
C5A | 0.054 (5) | 0.065 (4) | 0.042 (4) | −0.001 (4) | 0.007 (4) | −0.001 (3) |
C6A | 0.047 (4) | 0.049 (4) | 0.046 (4) | −0.008 (4) | 0.008 (4) | 0.001 (3) |
C7A | 0.075 (5) | 0.061 (5) | 0.085 (5) | 0.012 (4) | 0.027 (4) | 0.005 (4) |
C8A | 0.059 (4) | 0.076 (5) | 0.066 (5) | 0.008 (4) | −0.005 (4) | 0.007 (4) |
N1B | 0.047 (4) | 0.059 (4) | 0.048 (4) | −0.002 (3) | 0.023 (3) | 0.007 (3) |
N2B | 0.046 (3) | 0.092 (4) | 0.042 (3) | −0.008 (3) | 0.006 (3) | −0.013 (3) |
N3B | 0.048 (4) | 0.052 (3) | 0.037 (3) | 0.005 (3) | 0.027 (3) | 0.006 (3) |
C2B | 0.051 (5) | 0.047 (4) | 0.035 (4) | −0.012 (4) | 0.003 (4) | −0.002 (3) |
C4B | 0.046 (5) | 0.056 (5) | 0.063 (5) | 0.004 (4) | 0.034 (4) | 0.002 (4) |
C5B | 0.037 (4) | 0.071 (5) | 0.060 (5) | 0.001 (4) | 0.019 (4) | −0.001 (4) |
C6B | 0.052 (5) | 0.049 (4) | 0.040 (4) | −0.001 (4) | 0.007 (4) | −0.005 (3) |
C7B | 0.076 (5) | 0.058 (5) | 0.071 (5) | −0.011 (4) | 0.035 (4) | 0.006 (4) |
C8B | 0.063 (5) | 0.095 (6) | 0.052 (4) | −0.004 (4) | −0.005 (4) | −0.006 (4) |
N1C | 0.058 (4) | 0.053 (3) | 0.033 (3) | −0.003 (3) | 0.012 (3) | −0.004 (3) |
N2C | 0.062 (4) | 0.103 (4) | 0.033 (3) | 0.005 (3) | 0.016 (3) | 0.001 (3) |
N3C | 0.052 (4) | 0.064 (4) | 0.039 (3) | 0.001 (3) | 0.015 (3) | −0.007 (3) |
C2C | 0.034 (4) | 0.060 (4) | 0.049 (4) | 0.003 (4) | 0.008 (4) | −0.003 (4) |
C4C | 0.074 (6) | 0.031 (4) | 0.051 (5) | 0.006 (4) | 0.014 (4) | 0.015 (3) |
C5C | 0.031 (4) | 0.064 (5) | 0.071 (5) | −0.001 (4) | 0.016 (4) | −0.001 (4) |
C6C | 0.038 (4) | 0.038 (4) | 0.057 (4) | −0.011 (3) | 0.006 (4) | 0.002 (3) |
C7C | 0.069 (5) | 0.090 (6) | 0.076 (5) | 0.017 (4) | 0.044 (5) | 0.006 (4) |
C8C | 0.079 (5) | 0.081 (5) | 0.040 (4) | −0.008 (4) | −0.009 (3) | −0.009 (3) |
N1D | 0.061 (4) | 0.048 (3) | 0.029 (3) | −0.003 (3) | 0.017 (3) | 0.011 (2) |
N2D | 0.045 (4) | 0.108 (5) | 0.032 (3) | −0.002 (3) | 0.016 (3) | 0.009 (3) |
N3D | 0.046 (4) | 0.056 (4) | 0.047 (3) | 0.004 (3) | 0.013 (3) | 0.002 (3) |
C2D | 0.038 (4) | 0.046 (4) | 0.043 (4) | −0.008 (3) | 0.014 (4) | −0.009 (3) |
C4D | 0.066 (5) | 0.033 (4) | 0.043 (4) | 0.010 (4) | 0.024 (4) | 0.003 (3) |
C5D | 0.037 (4) | 0.069 (5) | 0.064 (5) | 0.005 (4) | 0.019 (4) | −0.003 (4) |
C6D | 0.047 (5) | 0.052 (4) | 0.062 (5) | −0.002 (4) | −0.002 (4) | −0.009 (4) |
C7D | 0.064 (5) | 0.067 (5) | 0.070 (5) | −0.013 (4) | 0.037 (4) | −0.008 (4) |
C8D | 0.059 (5) | 0.107 (6) | 0.050 (4) | −0.005 (4) | −0.004 (3) | 0.019 (4) |
O1A | 0.063 (3) | 0.095 (4) | 0.067 (3) | −0.011 (3) | 0.000 (3) | 0.002 (3) |
O2A | 0.066 (3) | 0.094 (3) | 0.041 (3) | 0.003 (3) | 0.007 (2) | 0.007 (3) |
O3A | 0.058 (3) | 0.115 (4) | 0.044 (3) | −0.018 (3) | 0.013 (2) | 0.002 (3) |
C9A | 0.060 (5) | 0.055 (5) | 0.059 (5) | 0.008 (4) | 0.013 (4) | −0.008 (4) |
C10A | 0.044 (5) | 0.052 (4) | 0.050 (5) | 0.006 (4) | 0.012 (4) | 0.000 (4) |
C11A | 0.072 (5) | 0.063 (5) | 0.043 (4) | 0.008 (4) | 0.009 (4) | 0.000 (4) |
C12A | 0.081 (6) | 0.088 (5) | 0.040 (4) | 0.000 (5) | 0.028 (4) | −0.006 (4) |
C13A | 0.066 (6) | 0.064 (5) | 0.078 (6) | 0.011 (4) | 0.052 (5) | 0.016 (4) |
C14A | 0.048 (5) | 0.082 (6) | 0.074 (6) | 0.010 (4) | 0.020 (5) | 0.014 (5) |
C15A | 0.062 (5) | 0.039 (4) | 0.047 (4) | 0.006 (4) | 0.021 (4) | −0.001 (3) |
O1B | 0.057 (3) | 0.151 (4) | 0.043 (3) | −0.003 (3) | 0.007 (2) | 0.006 (3) |
O2B | 0.066 (3) | 0.078 (3) | 0.042 (3) | 0.009 (3) | 0.012 (3) | −0.007 (3) |
O3B | 0.036 (3) | 0.104 (4) | 0.054 (3) | −0.002 (3) | 0.014 (2) | −0.019 (3) |
C9B | 0.057 (5) | 0.052 (4) | 0.042 (5) | 0.009 (4) | 0.018 (4) | 0.004 (4) |
C10B | 0.042 (4) | 0.031 (4) | 0.044 (4) | 0.009 (3) | 0.002 (3) | −0.012 (3) |
C11B | 0.061 (5) | 0.068 (5) | 0.042 (4) | −0.012 (4) | 0.014 (4) | 0.003 (4) |
C12B | 0.058 (5) | 0.080 (5) | 0.038 (4) | −0.012 (4) | 0.008 (4) | −0.009 (4) |
C13B | 0.058 (5) | 0.078 (5) | 0.057 (5) | −0.003 (4) | 0.030 (4) | −0.002 (4) |
C14B | 0.050 (5) | 0.084 (5) | 0.069 (5) | 0.005 (4) | 0.017 (4) | −0.011 (4) |
C15B | 0.038 (4) | 0.078 (5) | 0.037 (4) | 0.003 (4) | 0.014 (4) | 0.000 (4) |
O1C | 0.057 (3) | 0.135 (4) | 0.059 (3) | 0.003 (3) | 0.009 (2) | −0.004 (3) |
O2C | 0.058 (3) | 0.093 (4) | 0.036 (2) | 0.007 (3) | 0.014 (2) | 0.004 (3) |
O3C | 0.045 (3) | 0.104 (4) | 0.050 (3) | 0.006 (3) | 0.014 (2) | 0.006 (3) |
C9C | 0.066 (5) | 0.060 (5) | 0.036 (4) | 0.011 (4) | 0.024 (4) | 0.006 (4) |
C10C | 0.046 (5) | 0.051 (4) | 0.029 (4) | −0.004 (3) | 0.008 (3) | 0.003 (3) |
C11C | 0.033 (4) | 0.082 (5) | 0.065 (5) | 0.001 (4) | 0.028 (4) | −0.002 (4) |
C12C | 0.052 (5) | 0.098 (6) | 0.057 (5) | −0.011 (4) | 0.010 (4) | −0.012 (4) |
C13C | 0.079 (6) | 0.056 (4) | 0.044 (4) | −0.002 (4) | 0.018 (4) | −0.010 (4) |
C14C | 0.049 (5) | 0.056 (5) | 0.087 (6) | 0.001 (4) | 0.039 (4) | −0.008 (4) |
C15C | 0.044 (5) | 0.057 (5) | 0.059 (5) | 0.001 (4) | 0.000 (4) | −0.011 (4) |
O1D | 0.060 (3) | 0.102 (4) | 0.058 (3) | −0.007 (3) | 0.003 (3) | 0.001 (3) |
O2D | 0.062 (3) | 0.087 (3) | 0.034 (2) | 0.007 (3) | 0.013 (2) | 0.010 (2) |
O3D | 0.054 (3) | 0.125 (4) | 0.053 (3) | 0.000 (3) | 0.022 (3) | 0.006 (3) |
C9D | 0.074 (6) | 0.050 (4) | 0.041 (4) | 0.019 (4) | 0.027 (4) | 0.015 (4) |
C10D | 0.029 (4) | 0.052 (4) | 0.040 (4) | 0.003 (3) | 0.017 (3) | −0.007 (3) |
C11D | 0.045 (4) | 0.073 (5) | 0.039 (4) | −0.003 (3) | 0.007 (3) | 0.013 (3) |
C12D | 0.072 (6) | 0.091 (5) | 0.042 (4) | 0.007 (5) | 0.013 (4) | 0.010 (4) |
C13D | 0.056 (5) | 0.093 (5) | 0.049 (5) | 0.014 (4) | 0.019 (4) | 0.001 (4) |
C14D | 0.046 (5) | 0.069 (5) | 0.052 (5) | 0.000 (4) | 0.014 (4) | 0.000 (4) |
C15D | 0.061 (5) | 0.055 (5) | 0.042 (4) | 0.017 (4) | 0.004 (4) | 0.009 (4) |
O1A—C15A | 1.372 (9) | C8B—H8B2 | 0.9601 |
O2A—C9A | 1.272 (8) | C8B—H8B3 | 0.9592 |
O3A—C9A | 1.267 (9) | C4C—C5C | 1.387 (10) |
O1A—H1A1 | 0.8207 | C4C—C7C | 1.509 (10) |
N1A—C6A | 1.322 (9) | C5C—C6C | 1.355 (10) |
N1A—C2A | 1.354 (9) | C6C—C8C | 1.509 (9) |
O1B—C15B | 1.344 (8) | C5C—H5C | 0.9305 |
N2A—C2A | 1.318 (9) | C7C—H7C2 | 0.9606 |
O2B—C9B | 1.264 (8) | C7C—H7C1 | 0.9619 |
N3A—C2A | 1.337 (9) | C7C—H7C3 | 0.9598 |
N3A—C4A | 1.348 (9) | C8C—H8C2 | 0.9598 |
O3B—C9B | 1.262 (9) | C8C—H8C1 | 0.9594 |
N1A—H1A | 0.8595 | C8C—H8C3 | 0.9592 |
O1B—H1B1 | 0.8191 | C4D—C5D | 1.403 (10) |
N2A—H2A2 | 0.8604 | C4D—C7D | 1.490 (9) |
N2A—H2A1 | 0.8603 | C5D—C6D | 1.352 (9) |
N1B—C6B | 1.336 (8) | C6D—C8D | 1.516 (9) |
N1B—C2B | 1.371 (9) | C5D—H5D | 0.9294 |
O1C—C15C | 1.352 (8) | C7D—H7D1 | 0.9612 |
N2B—C2B | 1.325 (8) | C7D—H7D2 | 0.9594 |
O2C—C9C | 1.279 (8) | C7D—H7D3 | 0.9608 |
N3B—C4B | 1.343 (9) | C8D—H8D1 | 0.9608 |
N3B—C2B | 1.329 (9) | C8D—H8D2 | 0.9602 |
O3C—C9C | 1.246 (9) | C8D—H8D3 | 0.9601 |
N1B—H1B | 0.8599 | C9A—C10A | 1.473 (10) |
O1C—H1C1 | 0.8207 | C10A—C15A | 1.370 (10) |
N2B—H2B1 | 0.8609 | C10A—C11A | 1.414 (10) |
N2B—H2B2 | 0.8591 | C11A—C12A | 1.342 (10) |
N1C—C6C | 1.337 (9) | C12A—C13A | 1.386 (11) |
N1C—C2C | 1.366 (9) | C13A—C14A | 1.380 (12) |
O1D—C15D | 1.373 (8) | C14A—C15A | 1.368 (11) |
N2C—C2C | 1.327 (9) | C11A—H11A | 0.9298 |
O2D—C9D | 1.270 (8) | C12A—H12A | 0.9299 |
N3C—C4C | 1.288 (9) | C13A—H13A | 0.9299 |
N3C—C2C | 1.348 (9) | C14A—H14A | 0.9306 |
O3D—C9D | 1.252 (9) | C9B—C10B | 1.503 (10) |
N1C—H1C | 0.8604 | C10B—C11B | 1.397 (10) |
O1D—H1D1 | 0.8200 | C10B—C15B | 1.365 (10) |
N2C—H2C2 | 0.8591 | C11B—C12B | 1.366 (9) |
N2C—H2C1 | 0.8611 | C12B—C13B | 1.380 (9) |
N1D—C2D | 1.339 (9) | C13B—C14B | 1.378 (10) |
N1D—C6D | 1.363 (9) | C14B—C15B | 1.388 (10) |
N2D—C2D | 1.341 (8) | C11B—H11B | 0.9310 |
N3D—C2D | 1.346 (9) | C12B—H12B | 0.9302 |
N3D—C4D | 1.297 (10) | C13B—H13B | 0.9289 |
N1D—H1D | 0.8594 | C14B—H14B | 0.9301 |
N2D—H2D1 | 0.8602 | C9C—C10C | 1.496 (9) |
N2D—H2D2 | 0.8600 | C10C—C15C | 1.393 (9) |
C4A—C7A | 1.512 (9) | C10C—C11C | 1.375 (9) |
C4A—C5A | 1.379 (9) | C11C—C12C | 1.390 (10) |
C5A—C6A | 1.355 (9) | C12C—C13C | 1.335 (11) |
C6A—C8A | 1.500 (9) | C13C—C14C | 1.355 (10) |
C5A—H5A | 0.9297 | C14C—C15C | 1.396 (10) |
C7A—H7A3 | 0.9625 | C11C—H11C | 0.9308 |
C7A—H7A2 | 0.9617 | C12C—H12C | 0.9308 |
C7A—H7A1 | 0.9615 | C13C—H13C | 0.9313 |
C8A—H8A1 | 0.9599 | C14C—H14C | 0.9303 |
C8A—H8A3 | 0.9611 | C9D—C10D | 1.489 (10) |
C8A—H8A2 | 0.9605 | C10D—C15D | 1.407 (9) |
C4B—C5B | 1.395 (10) | C10D—C11D | 1.375 (9) |
C4B—C7B | 1.508 (10) | C11D—C12D | 1.397 (9) |
C5B—C6B | 1.339 (9) | C12D—C13D | 1.372 (10) |
C6B—C8B | 1.484 (7) | C13D—C14D | 1.361 (10) |
C5B—H5B | 0.9300 | C14D—C15D | 1.385 (10) |
C7B—H7B1 | 0.9609 | C11D—H11D | 0.9295 |
C7B—H7B3 | 0.9595 | C12D—H12D | 0.9304 |
C7B—H7B2 | 0.9603 | C13D—H13D | 0.9300 |
C8B—H8B1 | 0.9593 | C14D—H14D | 0.9303 |
O1A···O2A | 2.517 (6) | C2D···H2C2 | 3.0648 |
O1B···O1Di | 3.100 (6) | C4B···H2A1 | 3.0181 |
O1B···O2B | 2.577 (6) | C4C···H2D2 | 3.0443 |
O1C···O2C | 2.510 (6) | C4D···H2C2 | 3.0190 |
O1D···O1Bii | 3.100 (6) | C9A···H1A1 | 2.4616 |
O1D···O2D | 2.569 (6) | C9A···H1A | 2.6288 |
O2A···O1A | 2.517 (6) | C9A···H2A2 | 2.7726 |
O2A···N2A | 2.847 (6) | C9B···H2B2 | 2.8070 |
O2B···N2B | 2.888 (6) | C9B···H1B | 2.6247 |
O2B···C6C | 3.314 (7) | C9B···H1B1 | 2.4637 |
O2B···O1B | 2.577 (6) | C9C···H1C | 2.6201 |
O2C···O1C | 2.510 (6) | C9C···H1C1 | 2.4141 |
O2C···C12Biii | 3.416 (7) | C9C···H2C1 | 2.7921 |
O2C···N2C | 2.835 (6) | C9D···H1D | 2.6046 |
O2D···O1D | 2.569 (6) | C9D···H1D1 | 2.4758 |
O2D···N2D | 2.883 (6) | C9D···H2D1 | 2.8080 |
O3A···C8A | 3.295 (7) | C11A···H11Bviii | 3.0947 |
O3A···C6A | 3.401 (8) | C11B···H7C3 | 3.0776 |
O3A···N1A | 2.598 (7) | C11B···H7D1iv | 2.9365 |
O3B···N1B | 2.580 (6) | C11B···H11Aix | 3.0863 |
O3B···C8B | 3.318 (7) | C11C···H11Dviii | 3.0169 |
O3B···C6B | 3.396 (8) | C12A···H11Bviii | 3.0879 |
O3B···C2Div | 3.416 (7) | C12B···H7D1iv | 2.9002 |
O3C···N1C | 2.600 (7) | C12B···H7C3 | 2.8816 |
O3C···C2B | 3.343 (7) | C12C···H11Dviii | 3.0593 |
O3C···C8C | 3.357 (7) | C12C···H7B1 | 3.0606 |
O3D···N1D | 2.572 (7) | C13A···H7D3viii | 2.8186 |
O3D···C8D | 3.314 (7) | C13B···H7C3 | 2.8163 |
O1A···H8C3v | 2.7097 | C13B···H7D1iv | 3.0666 |
O1A···H5Avi | 2.7651 | C14A···H8A2vi | 3.0207 |
O1B···H5Bvii | 2.7923 | C14B···H7C3 | 2.9739 |
O1C···H5Cvi | 2.8267 | C14D···H8D2vii | 3.0798 |
O1D···H5Dvii | 2.8077 | C15A···H8C3v | 2.9155 |
O1D···H1B1ii | 2.8351 | H2B1···N3A | 2.2336 |
O2A···H1A | 2.9053 | H2B1···C2A | 3.0946 |
O2A···H8D1viii | 2.8480 | H1A···H8A1 | 2.3929 |
O2A···H1A1 | 1.8441 | H1A···H2A2 | 2.2250 |
O2A···H2A2 | 1.9901 | H1A···O3A | 1.7435 |
O2B···H1B | 2.9072 | H1A···O2A | 2.9053 |
O2B···H1B1 | 1.8807 | H1A···C9A | 2.6288 |
O2B···H2B2 | 2.0291 | H1B···H2B2 | 2.2481 |
O2C···H2C1 | 1.9763 | H1B···H8B3 | 2.3340 |
O2C···H1C1 | 1.7830 | H1B···C9B | 2.6247 |
O2C···H12Biii | 2.7322 | H1B···O3B | 1.7236 |
O2C···H1C | 2.9138 | H1B···O2B | 2.9072 |
O2D···H8A3ix | 2.7164 | H1C···H2C1 | 2.3190 |
O2D···H1D1 | 1.8689 | H1C···O2C | 2.9138 |
O2D···H2D1 | 2.0250 | H1C···H8C1 | 2.3290 |
O2D···H1D | 2.9120 | H1C···C9C | 2.6201 |
O3A···H11A | 2.5036 | H1C···O3C | 1.7407 |
O3A···H1A | 1.7435 | H1D···O2D | 2.9120 |
O3A···H2A2 | 2.9095 | H1D···C9D | 2.6046 |
O3A···H8A1 | 2.7941 | H1D···O3D | 1.7141 |
O3B···H11B | 2.4784 | H1D···H8D3 | 2.4877 |
O3B···H8B3 | 2.7203 | H1D···H2D1 | 2.2910 |
O3B···H1B | 1.7236 | H2B2···O2B | 2.0291 |
O3C···H1C | 1.7407 | H2B2···C9B | 2.8070 |
O3C···H11C | 2.4596 | H2B2···H1B | 2.2481 |
O3C···H8C1 | 2.8079 | H8B2···H14Bvi | 2.5956 |
O3D···H11D | 2.4647 | H8B2···H5B | 2.4486 |
O3D···H1D | 1.7141 | H8B3···O3B | 2.7203 |
N1A···C9Dviii | 3.321 (7) | H8B3···H1B | 2.3340 |
N1A···C9A | 3.446 (9) | H5A···H8A2 | 2.4502 |
N1A···O3A | 2.598 (7) | H5A···H7A1 | 2.4877 |
N1B···C9B | 3.447 (9) | H5A···O1Avii | 2.7651 |
N1B···O3B | 2.580 (6) | H5B···H7B2 | 2.5066 |
N1C···O3C | 2.600 (7) | H5B···H8B2 | 2.4486 |
N1C···C9C | 3.434 (9) | H5B···O1Bvi | 2.7923 |
N1D···O3D | 2.572 (7) | H5C···H7C2 | 2.3711 |
N1D···C9D | 3.424 (9) | H5C···H8C2 | 2.5460 |
N1D···C9Aix | 3.346 (8) | H5C···O1Cvii | 2.8267 |
N2A···O2A | 2.847 (6) | H5D···H8D2 | 2.5037 |
N2A···N3B | 2.946 (7) | H5D···H7D2 | 2.3211 |
N2B···O2B | 2.888 (6) | H5D···O1Dvi | 2.8077 |
N2B···N3A | 3.086 (7) | H7B1···H2A1 | 2.5521 |
N2C···N3D | 3.005 (6) | H7B1···C12C | 3.0606 |
N2C···O2C | 2.835 (6) | H7B2···H5B | 2.5066 |
N2D···O2D | 2.883 (6) | H7B3···C10Div | 3.0541 |
N2D···N3C | 3.021 (7) | H7B3···C15Div | 2.9501 |
N3A···N2B | 3.086 (7) | H7B3···C13Div | 2.8723 |
N3A···C13Cv | 3.432 (7) | H7B3···C12Div | 2.9543 |
N3B···N2A | 2.946 (7) | H7B3···C11Div | 3.0236 |
N3C···N2D | 3.021 (7) | H7B3···C14Div | 2.8436 |
N3D···C11Aix | 3.382 (8) | H2D1···C9D | 2.8080 |
N3D···N2C | 3.005 (6) | H2D1···O2D | 2.0250 |
N2B···H8C1 | 2.7993 | H2D1···H1D | 2.2910 |
N3A···H2B1 | 2.2336 | H2D2···C2C | 3.0588 |
N3B···H2A1 | 2.0912 | H2D2···C4C | 3.0443 |
N3C···H2D2 | 2.1631 | H2D2···N3C | 2.1631 |
N3D···H2C2 | 2.1466 | H8D1···O2Aix | 2.8480 |
C2A···C11Dviii | 3.572 (9) | H11A···O3A | 2.5036 |
C2A···C12Cv | 3.348 (10) | H11A···C11Bviii | 3.0863 |
C2A···C10Dviii | 3.523 (9) | H11A···H11Bviii | 2.5038 |
C2A···C13Cv | 3.474 (9) | H11B···O3B | 2.4784 |
C2B···O3C | 3.343 (7) | H11B···C11Aix | 3.0947 |
C2C···C13Ax | 3.582 (9) | H11B···C12Aix | 3.0879 |
C2C···C12Ax | 3.454 (9) | H11B···H11Aix | 2.5038 |
C2D···O3Biii | 3.416 (7) | H11B···H12Aix | 2.5044 |
C2D···C11Aix | 3.558 (8) | H11C···O3C | 2.4596 |
C2D···C10Aix | 3.567 (8) | H11C···C12Dviii | 3.0434 |
C4A···C13Cv | 3.497 (8) | H11C···C11Dviii | 3.0111 |
C4B···C10Div | 3.489 (8) | H11C···H11Dviii | 2.3960 |
C4B···C10C | 3.472 (8) | H11C···H12Dviii | 2.4825 |
C4C···C13Ax | 3.557 (8) | H11D···O3D | 2.4647 |
C4C···C10B | 3.470 (8) | H8D2···H5D | 2.5037 |
C4D···C10Biii | 3.450 (8) | H8D2···C14Dvi | 3.0798 |
C5A···C15Dviii | 3.444 (8) | H8D2···H14Dvi | 2.4215 |
C5A···C14Cv | 3.574 (8) | H12A···H11Bviii | 2.5044 |
C5B···C9Div | 3.533 (8) | H12B···O2Civ | 2.7322 |
C5B···C9C | 3.507 (9) | H12C···H11Dviii | 2.4930 |
C5C···C13Ax | 3.586 (8) | H8D3···H1D | 2.4877 |
C5C···C9B | 3.502 (8) | H13A···H14Bxi | 2.4854 |
C5C···C14Ax | 3.589 (9) | H13C···H14Dxi | 2.5571 |
C5C···C10B | 3.565 (8) | H7D1···C12Biii | 2.9002 |
C5D···C9Biii | 3.588 (8) | H7D1···C11Biii | 2.9365 |
C6A···O3A | 3.401 (8) | H7D1···C13Biii | 3.0666 |
C6A···C14Cv | 3.439 (8) | H14A···H8A2vi | 2.3900 |
C6B···C9Div | 3.564 (8) | H14B···H8B2vii | 2.5956 |
C6B···C9C | 3.534 (9) | H14B···H13Axii | 2.4854 |
C6B···O2Div | 3.372 (7) | H14C···H13Dxi | 2.5652 |
C6B···O3B | 3.396 (8) | H14D···H8D2vii | 2.4215 |
C6C···C9B | 3.437 (8) | H7D2···H5D | 2.3211 |
C6C···C14Ax | 3.389 (9) | H7D3···C13Aix | 2.8186 |
C6C···O2B | 3.314 (7) | H1B1···O1Di | 2.8351 |
C7B···C11C | 3.593 (9) | H1B1···C9B | 2.4637 |
C8A···O3A | 3.295 (7) | H1B1···O2B | 1.8807 |
C8B···O3B | 3.318 (7) | H1D1···O2D | 1.8689 |
C8C···O3C | 3.357 (7) | H1D1···C9D | 2.4758 |
C8D···O3D | 3.314 (7) | H2A1···N3B | 2.0912 |
C9A···N1A | 3.446 (9) | H2A1···C4B | 3.0181 |
C9A···N1Dviii | 3.346 (8) | H2A1···C2B | 3.0160 |
C9B···C5Div | 3.588 (8) | H2A1···H7B1 | 2.5521 |
C9B···C5C | 3.502 (8) | H2A2···C9A | 2.7726 |
C9B···N1B | 3.447 (9) | H2A2···H1A | 2.2250 |
C9B···C6C | 3.437 (8) | H2A2···O2A | 1.9901 |
C9C···N1C | 3.434 (9) | H2A2···O3A | 2.9095 |
C9C···C6B | 3.534 (9) | H2C1···O2C | 1.9763 |
C9C···C5B | 3.507 (9) | H2C1···C9C | 2.7921 |
C9D···N1D | 3.424 (9) | H2C1···H1C | 2.3190 |
C9D···N1Aix | 3.321 (7) | H2C2···C4D | 3.0190 |
C10A···C2Dviii | 3.567 (8) | H2C2···N3D | 2.1466 |
C10B···C5C | 3.565 (8) | H2C2···C2D | 3.0648 |
C10B···C4C | 3.470 (8) | H8A1···O3A | 2.7941 |
C10B···C4Div | 3.450 (8) | H8A1···H1A | 2.3929 |
C10C···C4B | 3.472 (8) | H8A2···H14Avii | 2.3900 |
C10D···C2Aix | 3.523 (9) | H8A2···H5A | 2.4502 |
C11A···C2Dviii | 3.558 (8) | H8A2···C14Avii | 3.0207 |
C11A···N3Dviii | 3.382 (8) | H8A3···O2Dviii | 2.7163 |
C11C···C7B | 3.593 (9) | H7A1···H5A | 2.4877 |
C11D···C2Aix | 3.572 (9) | H7A2···C14Di | 2.9614 |
C12A···C2Cv | 3.454 (9) | H7A2···H14Di | 2.5641 |
C12B···O2Civ | 3.416 (7) | H1A1···C9A | 2.4616 |
C12C···C2Ax | 3.348 (10) | H1A1···O2A | 1.8441 |
C13A···C5Cv | 3.586 (8) | H8C1···O3C | 2.8079 |
C13A···C2Cv | 3.582 (9) | H8C1···H1C | 2.3290 |
C13A···C4Cv | 3.557 (8) | H8C1···N2B | 2.7993 |
C13C···C4Ax | 3.497 (8) | H8C2···H5C | 2.5460 |
C13C···C2Ax | 3.474 (9) | H8C3···C15Ax | 2.9155 |
C13C···N3Ax | 3.432 (7) | H8C3···O1Ax | 2.7097 |
C14A···C5Cv | 3.589 (9) | H7C2···H5C | 2.3711 |
C14A···C6Cv | 3.389 (9) | H7C3···C13B | 2.8163 |
C14C···C6Ax | 3.439 (8) | H7C3···C11B | 3.0776 |
C14C···C5Ax | 3.574 (8) | H7C3···C12B | 2.8816 |
C15D···C5Aix | 3.444 (8) | H7C3···C14B | 2.9739 |
C2A···H2B1 | 3.0946 | H1C1···C9C | 2.4141 |
C2B···H2A1 | 3.0160 | H1C1···O2C | 1.7830 |
C2C···H2D2 | 3.0588 | ||
C15A—O1A—H1A1 | 109.70 | N1D—C2D—N3D | 123.0 (6) |
C2A—N1A—C6A | 120.3 (6) | N3D—C4D—C7D | 118.9 (6) |
C2A—N3A—C4A | 114.5 (6) | C5D—C4D—C7D | 118.7 (6) |
C2A—N1A—H1A | 119.88 | N3D—C4D—C5D | 122.3 (6) |
C6A—N1A—H1A | 119.78 | C4D—C5D—C6D | 118.3 (6) |
C15B—O1B—H1B1 | 109.99 | N1D—C6D—C8D | 114.8 (5) |
C2A—N2A—H2A1 | 120.18 | N1D—C6D—C5D | 119.3 (6) |
C2A—N2A—H2A2 | 119.82 | C5D—C6D—C8D | 125.9 (6) |
H2A1—N2A—H2A2 | 120.00 | C6D—C5D—H5D | 120.98 |
C2B—N1B—C6B | 120.3 (5) | C4D—C5D—H5D | 120.75 |
C2B—N3B—C4B | 116.3 (6) | C4D—C7D—H7D3 | 109.35 |
C6B—N1B—H1B | 119.94 | H7D2—C7D—H7D3 | 109.48 |
C2B—N1B—H1B | 119.71 | C4D—C7D—H7D1 | 109.00 |
C15C—O1C—H1C1 | 109.29 | H7D1—C7D—H7D3 | 109.40 |
H2B1—N2B—H2B2 | 119.92 | C4D—C7D—H7D2 | 110.09 |
C2B—N2B—H2B1 | 120.83 | H7D1—C7D—H7D2 | 109.51 |
C2B—N2B—H2B2 | 119.25 | C6D—C8D—H8D3 | 109.27 |
C2C—N1C—C6C | 120.2 (6) | H8D2—C8D—H8D3 | 109.45 |
C2C—N3C—C4C | 117.1 (6) | H8D1—C8D—H8D3 | 109.45 |
C6C—N1C—H1C | 119.78 | C6D—C8D—H8D2 | 109.98 |
C2C—N1C—H1C | 120.01 | C6D—C8D—H8D1 | 109.27 |
C15D—O1D—H1D1 | 109.80 | H8D1—C8D—H8D2 | 109.41 |
H2C1—N2C—H2C2 | 119.96 | O2A—C9A—O3A | 123.8 (6) |
C2C—N2C—H2C2 | 119.61 | O3A—C9A—C10A | 118.9 (6) |
C2C—N2C—H2C1 | 120.43 | O2A—C9A—C10A | 117.2 (6) |
C2D—N1D—C6D | 119.2 (6) | C9A—C10A—C15A | 122.6 (6) |
C2D—N3D—C4D | 118.0 (6) | C11A—C10A—C15A | 116.9 (6) |
C2D—N1D—H1D | 120.68 | C9A—C10A—C11A | 120.5 (6) |
C6D—N1D—H1D | 120.12 | C10A—C11A—C12A | 121.8 (6) |
C2D—N2D—H2D1 | 120.49 | C11A—C12A—C13A | 119.6 (7) |
C2D—N2D—H2D2 | 119.44 | C12A—C13A—C14A | 120.3 (7) |
H2D1—N2D—H2D2 | 120.06 | C13A—C14A—C15A | 119.0 (7) |
N1A—C2A—N3A | 123.7 (7) | C10A—C15A—C14A | 122.4 (7) |
N1A—C2A—N2A | 116.9 (6) | O1A—C15A—C10A | 120.9 (6) |
N2A—C2A—N3A | 119.4 (6) | O1A—C15A—C14A | 116.7 (7) |
C5A—C4A—C7A | 121.8 (6) | C12A—C11A—H11A | 119.08 |
N3A—C4A—C7A | 114.0 (6) | C10A—C11A—H11A | 119.13 |
N3A—C4A—C5A | 124.2 (6) | C11A—C12A—H12A | 120.07 |
C4A—C5A—C6A | 117.5 (6) | C13A—C12A—H12A | 120.30 |
N1A—C6A—C8A | 116.2 (6) | C12A—C13A—H13A | 119.48 |
N1A—C6A—C5A | 119.8 (6) | C14A—C13A—H13A | 120.23 |
C5A—C6A—C8A | 124.0 (6) | C13A—C14A—H14A | 119.98 |
C4A—C5A—H5A | 121.37 | C15A—C14A—H14A | 121.00 |
C6A—C5A—H5A | 121.18 | O2B—C9B—O3B | 123.4 (6) |
H7A2—C7A—H7A3 | 109.37 | O2B—C9B—C10B | 118.3 (6) |
C4A—C7A—H7A3 | 109.66 | O3B—C9B—C10B | 118.3 (6) |
H7A1—C7A—H7A2 | 109.34 | C9B—C10B—C11B | 119.5 (6) |
C4A—C7A—H7A1 | 109.55 | C9B—C10B—C15B | 121.7 (6) |
H7A1—C7A—H7A3 | 109.28 | C11B—C10B—C15B | 118.8 (6) |
C4A—C7A—H7A2 | 109.63 | C10B—C11B—C12B | 121.6 (6) |
H8A1—C8A—H8A3 | 109.45 | C11B—C12B—C13B | 118.7 (6) |
C6A—C8A—H8A2 | 108.99 | C12B—C13B—C14B | 120.8 (6) |
H8A2—C8A—H8A3 | 109.35 | C13B—C14B—C15B | 119.5 (6) |
H8A1—C8A—H8A2 | 109.53 | C10B—C15B—C14B | 120.6 (6) |
C6A—C8A—H8A3 | 109.92 | O1B—C15B—C10B | 123.0 (6) |
C6A—C8A—H8A1 | 109.57 | O1B—C15B—C14B | 116.4 (6) |
N1B—C2B—N2B | 117.4 (6) | C12B—C11B—H11B | 119.09 |
N2B—C2B—N3B | 120.1 (6) | C10B—C11B—H11B | 119.35 |
N1B—C2B—N3B | 122.5 (6) | C11B—C12B—H12B | 120.24 |
N3B—C4B—C7B | 115.1 (6) | C13B—C12B—H12B | 121.01 |
C5B—C4B—C7B | 122.1 (6) | C12B—C13B—H13B | 118.84 |
N3B—C4B—C5B | 122.8 (6) | C14B—C13B—H13B | 120.34 |
C4B—C5B—C6B | 118.4 (6) | C15B—C14B—H14B | 120.40 |
N1B—C6B—C5B | 119.6 (5) | C13B—C14B—H14B | 120.05 |
N1B—C6B—C8B | 117.1 (5) | O3C—C9C—C10C | 120.0 (6) |
C5B—C6B—C8B | 123.3 (6) | O2C—C9C—O3C | 124.3 (6) |
C6B—C5B—H5B | 121.15 | O2C—C9C—C10C | 115.7 (6) |
C4B—C5B—H5B | 120.46 | C11C—C10C—C15C | 118.1 (6) |
H7B1—C7B—H7B2 | 109.42 | C9C—C10C—C11C | 118.7 (6) |
H7B1—C7B—H7B3 | 109.36 | C9C—C10C—C15C | 123.2 (5) |
C4B—C7B—H7B3 | 110.06 | C10C—C11C—C12C | 121.3 (6) |
C4B—C7B—H7B1 | 109.95 | C11C—C12C—C13C | 119.3 (6) |
H7B2—C7B—H7B3 | 109.49 | C12C—C13C—C14C | 121.8 (7) |
C4B—C7B—H7B2 | 108.53 | C13C—C14C—C15C | 119.8 (6) |
H8B2—C8B—H8B3 | 109.54 | C10C—C15C—C14C | 119.7 (6) |
C6B—C8B—H8B2 | 109.23 | O1C—C15C—C10C | 119.6 (6) |
H8B1—C8B—H8B2 | 109.45 | O1C—C15C—C14C | 120.8 (6) |
C6B—C8B—H8B3 | 109.51 | C12C—C11C—H11C | 119.62 |
C6B—C8B—H8B1 | 109.55 | C10C—C11C—H11C | 119.03 |
H8B1—C8B—H8B3 | 109.54 | C11C—C12C—H12C | 120.31 |
N1C—C2C—N3C | 122.1 (6) | C13C—C12C—H12C | 120.42 |
N1C—C2C—N2C | 119.2 (6) | C12C—C13C—H13C | 119.43 |
N2C—C2C—N3C | 118.7 (6) | C14C—C13C—H13C | 118.73 |
N3C—C4C—C7C | 117.5 (6) | C15C—C14C—H14C | 119.75 |
C5C—C4C—C7C | 119.2 (7) | C13C—C14C—H14C | 120.49 |
N3C—C4C—C5C | 123.2 (7) | O2D—C9D—C10D | 118.3 (6) |
C4C—C5C—C6C | 119.2 (6) | O3D—C9D—C10D | 117.2 (6) |
N1C—C6C—C5C | 118.1 (6) | O2D—C9D—O3D | 124.5 (6) |
C5C—C6C—C8C | 126.1 (6) | C9D—C10D—C15D | 121.6 (6) |
N1C—C6C—C8C | 115.8 (6) | C11D—C10D—C15D | 117.4 (6) |
C6C—C5C—H5C | 120.34 | C9D—C10D—C11D | 121.0 (5) |
C4C—C5C—H5C | 120.45 | C10D—C11D—C12D | 121.7 (5) |
C4C—C7C—H7C2 | 109.93 | C11D—C12D—C13D | 119.4 (6) |
C4C—C7C—H7C3 | 109.61 | C12D—C13D—C14D | 120.5 (7) |
H7C1—C7C—H7C2 | 109.27 | C13D—C14D—C15D | 120.2 (6) |
C4C—C7C—H7C1 | 109.08 | O1D—C15D—C14D | 117.5 (6) |
H7C2—C7C—H7C3 | 109.54 | C10D—C15D—C14D | 120.9 (6) |
H7C1—C7C—H7C3 | 109.40 | O1D—C15D—C10D | 121.6 (6) |
C6C—C8C—H8C3 | 109.57 | C10D—C11D—H11D | 119.19 |
H8C1—C8C—H8C3 | 109.50 | C12D—C11D—H11D | 119.15 |
C6C—C8C—H8C1 | 109.20 | C11D—C12D—H12D | 120.53 |
H8C1—C8C—H8C2 | 109.54 | C13D—C12D—H12D | 120.11 |
C6C—C8C—H8C2 | 109.61 | C12D—C13D—H13D | 120.09 |
H8C2—C8C—H8C3 | 109.42 | C14D—C13D—H13D | 119.36 |
N2D—C2D—N3D | 118.7 (6) | C13D—C14D—H14D | 119.96 |
N1D—C2D—N2D | 118.2 (6) | C15D—C14D—H14D | 119.87 |
C2A—N1A—C6A—C5A | −1.4 (8) | C9A—C10A—C15A—C14A | 179.9 (6) |
C2A—N1A—C6A—C8A | 178.1 (5) | C11A—C10A—C15A—O1A | 179.7 (5) |
C6A—N1A—C2A—N3A | −0.2 (9) | C15A—C10A—C11A—C12A | 1.1 (9) |
C6A—N1A—C2A—N2A | 179.1 (6) | C11A—C10A—C15A—C14A | −2.6 (9) |
C2A—N3A—C4A—C5A | −2.0 (8) | C10A—C11A—C12A—C13A | 0.0 (10) |
C4A—N3A—C2A—N1A | 1.9 (9) | C11A—C12A—C13A—C14A | 0.2 (10) |
C4A—N3A—C2A—N2A | −177.4 (6) | C12A—C13A—C14A—C15A | −1.6 (10) |
C2A—N3A—C4A—C7A | −179.3 (5) | C13A—C14A—C15A—C10A | 2.9 (10) |
C2B—N1B—C6B—C5B | 1.8 (8) | C13A—C14A—C15A—O1A | −179.4 (6) |
C6B—N1B—C2B—N2B | 178.9 (5) | O3B—C9B—C10B—C11B | 0.3 (8) |
C2B—N1B—C6B—C8B | −178.5 (5) | O2B—C9B—C10B—C11B | −178.8 (5) |
C6B—N1B—C2B—N3B | −1.9 (8) | O2B—C9B—C10B—C15B | 3.5 (8) |
C4B—N3B—C2B—N2B | −179.6 (5) | O3B—C9B—C10B—C15B | −177.4 (5) |
C2B—N3B—C4B—C5B | −0.6 (8) | C11B—C10B—C15B—C14B | 2.0 (8) |
C4B—N3B—C2B—N1B | 1.3 (8) | C9B—C10B—C11B—C12B | −179.1 (5) |
C2B—N3B—C4B—C7B | 179.9 (5) | C15B—C10B—C11B—C12B | −1.3 (9) |
C2C—N1C—C6C—C5C | −1.4 (8) | C9B—C10B—C15B—O1B | −2.2 (9) |
C6C—N1C—C2C—N3C | 2.1 (8) | C9B—C10B—C15B—C14B | 179.7 (5) |
C6C—N1C—C2C—N2C | −178.3 (5) | C11B—C10B—C15B—O1B | −180.0 (6) |
C2C—N1C—C6C—C8C | −179.5 (5) | C10B—C11B—C12B—C13B | 0.3 (9) |
C2C—N3C—C4C—C5C | 1.4 (9) | C11B—C12B—C13B—C14B | 0.1 (8) |
C4C—N3C—C2C—N2C | 178.4 (5) | C12B—C13B—C14B—C15B | 0.5 (9) |
C4C—N3C—C2C—N1C | −2.0 (9) | C13B—C14B—C15B—C10B | −1.6 (9) |
C2C—N3C—C4C—C7C | 180.0 (5) | C13B—C14B—C15B—O1B | −179.8 (5) |
C6D—N1D—C2D—N3D | 1.2 (8) | O2C—C9C—C10C—C11C | 178.8 (6) |
C2D—N1D—C6D—C8D | 179.6 (5) | O3C—C9C—C10C—C11C | 0.4 (9) |
C6D—N1D—C2D—N2D | 179.8 (5) | O3C—C9C—C10C—C15C | 179.4 (6) |
C2D—N1D—C6D—C5D | −1.9 (8) | O2C—C9C—C10C—C15C | −2.1 (9) |
C4D—N3D—C2D—N1D | 0.5 (9) | C9C—C10C—C11C—C12C | 177.6 (6) |
C2D—N3D—C4D—C7D | −178.5 (5) | C11C—C10C—C15C—C14C | 0.2 (9) |
C2D—N3D—C4D—C5D | −1.4 (9) | C9C—C10C—C15C—O1C | 1.2 (9) |
C4D—N3D—C2D—N2D | −178.1 (5) | C9C—C10C—C15C—C14C | −178.9 (6) |
C7A—C4A—C5A—C6A | 177.6 (5) | C15C—C10C—C11C—C12C | −1.5 (10) |
N3A—C4A—C5A—C6A | 0.6 (9) | C11C—C10C—C15C—O1C | −179.8 (6) |
C4A—C5A—C6A—N1A | 1.2 (8) | C10C—C11C—C12C—C13C | 2.7 (10) |
C4A—C5A—C6A—C8A | −178.2 (5) | C11C—C12C—C13C—C14C | −2.4 (10) |
C7B—C4B—C5B—C6B | −180.0 (5) | C12C—C13C—C14C—C15C | 1.1 (9) |
N3B—C4B—C5B—C6B | 0.6 (9) | C13C—C14C—C15C—C10C | 0.0 (9) |
C4B—C5B—C6B—C8B | 179.1 (5) | C13C—C14C—C15C—O1C | 180.0 (6) |
C4B—C5B—C6B—N1B | −1.2 (8) | O2D—C9D—C10D—C15D | 3.3 (8) |
N3C—C4C—C5C—C6C | −0.8 (9) | O3D—C9D—C10D—C11D | 1.2 (8) |
C7C—C4C—C5C—C6C | −179.3 (5) | O2D—C9D—C10D—C11D | −179.5 (5) |
C4C—C5C—C6C—C8C | 178.7 (5) | O3D—C9D—C10D—C15D | −176.1 (5) |
C4C—C5C—C6C—N1C | 0.8 (8) | C15D—C10D—C11D—C12D | −1.2 (9) |
C7D—C4D—C5D—C6D | 177.8 (5) | C9D—C10D—C11D—C12D | −178.6 (6) |
N3D—C4D—C5D—C6D | 0.6 (9) | C11D—C10D—C15D—O1D | −178.1 (5) |
C4D—C5D—C6D—C8D | 179.3 (6) | C11D—C10D—C15D—C14D | −0.5 (8) |
C4D—C5D—C6D—N1D | 1.1 (8) | C9D—C10D—C15D—O1D | −0.8 (9) |
O2A—C9A—C10A—C11A | 177.3 (6) | C9D—C10D—C15D—C14D | 176.8 (5) |
O2A—C9A—C10A—C15A | −5.3 (9) | C10D—C11D—C12D—C13D | 1.0 (10) |
O3A—C9A—C10A—C15A | 177.3 (6) | C11D—C12D—C13D—C14D | 1.1 (10) |
O3A—C9A—C10A—C11A | −0.1 (9) | C12D—C13D—C14D—C15D | −2.8 (10) |
C9A—C10A—C11A—C12A | 178.7 (6) | C13D—C14D—C15D—C10D | 2.6 (9) |
C9A—C10A—C15A—O1A | 2.2 (9) | C13D—C14D—C15D—O1D | −179.7 (6) |
Symmetry codes: (i) −x−1, y+1/2, −z+1; (ii) −x−1, y−1/2, −z+1; (iii) −x, y−1/2, −z+1; (iv) −x, y+1/2, −z+1; (v) −x, y+1/2, −z; (vi) x+1, y, z; (vii) x−1, y, z; (viii) x, y, z−1; (ix) x, y, z+1; (x) −x, y−1/2, −z; (xi) x+1, y, z−1; (xii) x−1, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2B—H2B1···N3A | 0.86 | 2.23 | 3.086 (7) | 171 |
N1A—H1A···O3A | 0.86 | 1.74 | 2.598 (7) | 172 |
N1B—H1B···O3B | 0.86 | 1.72 | 2.580 (6) | 174 |
N1C—H1C···O3C | 0.86 | 1.74 | 2.600 (7) | 177 |
N1D—H1D···O3D | 0.86 | 1.71 | 2.572 (7) | 176 |
N2B—H2B2···O2B | 0.86 | 2.03 | 2.888 (6) | 178 |
N2D—H2D1···O2D | 0.86 | 2.03 | 2.883 (6) | 175 |
N2D—H2D2···N3C | 0.86 | 2.16 | 3.021 (7) | 175 |
O1B—H1B1···O2B | 0.82 | 1.88 | 2.577 (6) | 142 |
O1D—H1D1···O2D | 0.82 | 1.87 | 2.569 (6) | 143 |
N2A—H2A1···N3B | 0.86 | 2.09 | 2.946 (7) | 172 |
N2A—H2A2···O2A | 0.86 | 1.99 | 2.847 (6) | 174 |
N2C—H2C1···O2C | 0.86 | 1.98 | 2.835 (6) | 175 |
N2C—H2C2···N3D | 0.86 | 2.15 | 3.005 (6) | 177 |
O1A—H1A1···O2A | 0.82 | 1.84 | 2.517 (6) | 138 |
O1C—H1C1···O2C | 0.82 | 1.78 | 2.510 (6) | 147 |
C11C—H11C···O3C | 0.93 | 2.46 | 2.782 (8) | 100 |
Experimental details
Crystal data | |
Chemical formula | C6H10N3+·C7H5O3− |
Mr | 261.28 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 295 |
a, b, c (Å) | 11.039 (2), 13.995 (3), 17.371 (3) |
β (°) | 99.04 (3) |
V (Å3) | 2650.3 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.45 × 0.3 × 0.2 |
Data collection | |
Diffractometer | Kuma KM-4 CCD κ-geometry diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20586, 4865, 2229 |
Rint | 0.082 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.082, 0.90 |
No. of reflections | 4865 |
No. of parameters | 698 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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.
O1A—C15A | 1.372 (9) | N3B—C4B | 1.343 (9) |
O2A—C9A | 1.272 (8) | N3B—C2B | 1.329 (9) |
O3A—C9A | 1.267 (9) | O3C—C9C | 1.246 (9) |
N1A—C6A | 1.322 (9) | N1C—C6C | 1.337 (9) |
N1A—C2A | 1.354 (9) | N1C—C2C | 1.366 (9) |
O1B—C15B | 1.344 (8) | O1D—C15D | 1.373 (8) |
N2A—C2A | 1.318 (9) | N2C—C2C | 1.327 (9) |
O2B—C9B | 1.264 (8) | O2D—C9D | 1.270 (8) |
N3A—C2A | 1.337 (9) | N3C—C4C | 1.288 (9) |
N3A—C4A | 1.348 (9) | N3C—C2C | 1.348 (9) |
O3B—C9B | 1.262 (9) | O3D—C9D | 1.252 (9) |
N1B—C6B | 1.336 (8) | N1D—C2D | 1.339 (9) |
N1B—C2B | 1.371 (9) | N1D—C6D | 1.363 (9) |
O1C—C15C | 1.352 (8) | N2D—C2D | 1.341 (8) |
N2B—C2B | 1.325 (8) | N3D—C2D | 1.346 (9) |
O2C—C9C | 1.279 (8) | N3D—C4D | 1.297 (10) |
C2A—N1A—C6A | 120.3 (6) | N1C—C6C—C8C | 115.8 (6) |
C2A—N3A—C4A | 114.5 (6) | N2D—C2D—N3D | 118.7 (6) |
C2B—N1B—C6B | 120.3 (5) | N1D—C2D—N2D | 118.2 (6) |
C2B—N3B—C4B | 116.3 (6) | N1D—C2D—N3D | 123.0 (6) |
C2C—N1C—C6C | 120.2 (6) | N3D—C4D—C7D | 118.9 (6) |
C2C—N3C—C4C | 117.1 (6) | N3D—C4D—C5D | 122.3 (6) |
C2D—N1D—C6D | 119.2 (6) | N1D—C6D—C8D | 114.8 (5) |
C2D—N3D—C4D | 118.0 (6) | N1D—C6D—C5D | 119.3 (6) |
N1A—C2A—N3A | 123.7 (7) | O2A—C9A—O3A | 123.8 (6) |
N1A—C2A—N2A | 116.9 (6) | O3A—C9A—C10A | 118.9 (6) |
N2A—C2A—N3A | 119.4 (6) | O2A—C9A—C10A | 117.2 (6) |
N3A—C4A—C7A | 114.0 (6) | O1A—C15A—C10A | 120.9 (6) |
N3A—C4A—C5A | 124.2 (6) | O1A—C15A—C14A | 116.7 (7) |
N1A—C6A—C8A | 116.2 (6) | O2B—C9B—O3B | 123.4 (6) |
N1A—C6A—C5A | 119.8 (6) | O2B—C9B—C10B | 118.3 (6) |
N1B—C2B—N2B | 117.4 (6) | O3B—C9B—C10B | 118.3 (6) |
N2B—C2B—N3B | 120.1 (6) | O1B—C15B—C10B | 123.0 (6) |
N1B—C2B—N3B | 122.5 (6) | O1B—C15B—C14B | 116.4 (6) |
N3B—C4B—C7B | 115.1 (6) | O3C—C9C—C10C | 120.0 (6) |
N3B—C4B—C5B | 122.8 (6) | O2C—C9C—O3C | 124.3 (6) |
N1B—C6B—C5B | 119.6 (5) | O2C—C9C—C10C | 115.7 (6) |
N1B—C6B—C8B | 117.1 (5) | O1C—C15C—C10C | 119.6 (6) |
N1C—C2C—N3C | 122.1 (6) | O1C—C15C—C14C | 120.8 (6) |
N1C—C2C—N2C | 119.2 (6) | O2D—C9D—C10D | 118.3 (6) |
N2C—C2C—N3C | 118.7 (6) | O3D—C9D—C10D | 117.2 (6) |
N3C—C4C—C7C | 117.5 (6) | O2D—C9D—O3D | 124.5 (6) |
N3C—C4C—C5C | 123.2 (7) | O1D—C15D—C14D | 117.5 (6) |
N1C—C6C—C5C | 118.1 (6) | O1D—C15D—C10D | 121.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2B—H2B1···N3A | 0.86 | 2.23 | 3.086 (7) | 171 |
N1A—H1A···O3A | 0.86 | 1.74 | 2.598 (7) | 172 |
N1B—H1B···O3B | 0.86 | 1.72 | 2.580 (6) | 174 |
N1C—H1C···O3C | 0.86 | 1.74 | 2.600 (7) | 177 |
N1D—H1D···O3D | 0.86 | 1.71 | 2.572 (7) | 176 |
N2B—H2B2···O2B | 0.86 | 2.03 | 2.888 (6) | 178 |
N2D—H2D1···O2D | 0.86 | 2.03 | 2.883 (6) | 175 |
N2D—H2D2···N3C | 0.86 | 2.16 | 3.021 (7) | 175 |
O1B—H1B1···O2B | 0.82 | 1.88 | 2.577 (6) | 142 |
O1D—H1D1···O2D | 0.82 | 1.87 | 2.569 (6) | 143 |
N2A—H2A1···N3B | 0.86 | 2.09 | 2.946 (7) | 172 |
N2A—H2A2···O2A | 0.86 | 1.99 | 2.847 (6) | 174 |
N2C—H2C1···O2C | 0.86 | 1.98 | 2.835 (6) | 175 |
N2C—H2C2···N3D | 0.86 | 2.15 | 3.005 (6) | 177 |
O1A—H1A1···O2A | 0.82 | 1.84 | 2.517 (6) | 138 |
O1C—H1C1···O2C | 0.82 | 1.78 | 2.510 (6) | 147 |
C11C—H11C···O3C | 0.93 | 2.46 | 2.782 (8) | 100 |
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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 π–π 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).