In the crystal structures of 2-amino-4,6-dimethoxypyrimidinium 2,4,6-trinitrophenolate (picrate), C
6H
10N
3O
2+·C
6H
2N
3O
7−, (I), and 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium (pyrimethaminium or PMN) picrate dimethyl sulfoxide solvate, C
12H
14ClN
4+·C
6H
2N
3O
7−·C
2H
6OS, (II), the 2-amino-4,6-dimethoxypyrimidine and PMN cations are protonated at one of the pyrimidine N atoms. The picrate anion interacts with the protonated cations through bifurcated N—H
O hydrogen bonds, forming
R21(6) and
R12(6) ring motifs. In (I),
Z′ = 2. In (II), two inversion-related PMN cations are connected through a pair of N—H
N hydrogen bonds involving the 4-amino group and the uncharged N atom of the pyrimidine ring, forming a cyclic hydrogen-bonded
R22(8) motif. In addition to the pairing, the O atom of the dimethyl sulfoxide solvent molecule bridges the 2-amino and 4-amino groups on both sides of the paired bases, resulting in a self-complementary …
DADA… array of quadruple hydrogen-bonding patterns.
Supporting information
CCDC references: 688452; 724199
Compound (I) was prepared by mixing a hot methanol solution (20 ml) of
2-amino-4,6-dimethoxypyrimidine (38 mg) and picric acid (57 mg) and warming
the solution for half an hour over a water bath. The solution was cooled
slowly and kept at room temperature. After a few days, yellow plate-like
crystals were obtained. Compound (II) was prepared by heating hot methanol
solutions of pyrimethamine (62 mg, Shah Pharma Chemicals, India) and picric
acid (57 mg, Merck) for 20 min; the solution became turbid. In order to obtain
a clear solution, a few drops of DMSO was added. After about a week, thin
yellow plates of (II) were obtained.
All H atoms were positioned geometrically and were treated as riding. The C—H
and N—H bond lengths are 0.93–0.96 and 0.86 Å, respectively, for (I),
and 0.95–0.99 and 0.88 Å, for (II). The constraint Uiso(H) =
1.2Ueq(carrier) or 1.5Ueq(methyl carrier) was applied as
appropriate.
Data collection: COLLECT (Hooft, 1998) for (I); CrysAlis CCD (Oxford Diffraction, 2007) for (II). Cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998) for (I); CrysAlis CCD (Oxford Diffraction, 2007) for (II). Data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998) for (I); CrysAlis RED (Oxford Diffraction, 2007 for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).
(I) 2-amino-4,6-dimethoxypyrimidinium 2,4,6-trinitrophenolate
top
Crystal data top
C6H10N3O2+·C6H2N3O7− | Z = 4 |
Mr = 384.28 | F(000) = 792 |
Triclinic, P1 | Dx = 1.658 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8796 (2) Å | Cell parameters from 25 reflections |
b = 13.2847 (3) Å | θ = 3.0–27.6° |
c = 14.1395 (3) Å | µ = 0.14 mm−1 |
α = 99.820 (1)° | T = 120 K |
β = 100.701 (1)° | Plate-like, yellow |
γ = 105.095 (1)° | 0.16 × 0.12 × 0.06 mm |
V = 1539.68 (6) Å3 | |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 5725 reflections with I > 2σ(I) |
Radiation source: Bruker–Nonius FR591 rotating anode | Rint = 0.039 |
Graphite monochromator | θmax = 27.6°, θmin = 3.0° |
Detector resolution: 9.091 pixels mm-1 | h = −11→11 |
ϕ and ω scans | k = −17→17 |
27465 measured reflections | l = −17→18 |
7048 independent reflections | |
Refinement top
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0323P)2 + 1.7779P] where P = (Fo2 + 2Fc2)/3 |
7048 reflections | (Δ/σ)max = 0.001 |
487 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Crystal data top
C6H10N3O2+·C6H2N3O7− | γ = 105.095 (1)° |
Mr = 384.28 | V = 1539.68 (6) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.8796 (2) Å | Mo Kα radiation |
b = 13.2847 (3) Å | µ = 0.14 mm−1 |
c = 14.1395 (3) Å | T = 120 K |
α = 99.820 (1)° | 0.16 × 0.12 × 0.06 mm |
β = 100.701 (1)° | |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 5725 reflections with I > 2σ(I) |
27465 measured reflections | Rint = 0.039 |
7048 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.67 e Å−3 |
7048 reflections | Δρmin = −0.40 e Å−3 |
487 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su'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 | x | y | z | Uiso*/Ueq | |
O1A | 0.51490 (17) | 0.80162 (11) | 0.49974 (10) | 0.0239 (4) | |
O2A | 0.24861 (17) | 0.97367 (11) | 0.70206 (10) | 0.0221 (4) | |
N1A | 0.38352 (19) | 0.86439 (12) | 0.75249 (11) | 0.0181 (4) | |
N2A | 0.5155 (2) | 0.75255 (13) | 0.81357 (12) | 0.0224 (5) | |
N3A | 0.51840 (19) | 0.77285 (13) | 0.65556 (12) | 0.0203 (5) | |
C2A | 0.4726 (2) | 0.79610 (14) | 0.73939 (14) | 0.0182 (5) | |
C4A | 0.4717 (2) | 0.81982 (15) | 0.58449 (14) | 0.0199 (5) | |
C5A | 0.3768 (2) | 0.88854 (15) | 0.59051 (14) | 0.0204 (5) | |
C6A | 0.3341 (2) | 0.91031 (14) | 0.67775 (14) | 0.0184 (5) | |
C7A | 0.6251 (3) | 0.73974 (18) | 0.49217 (16) | 0.0280 (6) | |
C8A | 0.1954 (3) | 1.02904 (17) | 0.62878 (15) | 0.0266 (6) | |
O1B | 0.97010 (17) | 0.28292 (12) | 1.24768 (10) | 0.0257 (4) | |
O2B | 0.76467 (17) | 0.47940 (11) | 1.03643 (10) | 0.0231 (4) | |
N1B | 0.90269 (19) | 0.36924 (12) | 0.99084 (12) | 0.0190 (5) | |
N2B | 1.0488 (2) | 0.26189 (13) | 0.93427 (12) | 0.0217 (5) | |
N3B | 1.0145 (2) | 0.26976 (13) | 1.09213 (12) | 0.0215 (5) | |
C2B | 0.9894 (2) | 0.29994 (15) | 1.00671 (14) | 0.0189 (5) | |
C4B | 0.9510 (2) | 0.31102 (16) | 1.16149 (14) | 0.0212 (5) | |
C5B | 0.8633 (2) | 0.38392 (16) | 1.15245 (14) | 0.0217 (6) | |
C6B | 0.8408 (2) | 0.41204 (15) | 1.06385 (14) | 0.0192 (5) | |
C7B | 1.0624 (3) | 0.20959 (19) | 1.26254 (16) | 0.0308 (7) | |
C8B | 0.6811 (3) | 0.52224 (17) | 1.10435 (16) | 0.0270 (6) | |
O3A | 0.40970 (17) | 0.87674 (11) | 0.94919 (10) | 0.0223 (4) | |
O4A | 0.2244 (2) | 0.99548 (13) | 0.89815 (10) | 0.0336 (5) | |
O5A | 0.1611 (2) | 1.09046 (12) | 1.01424 (11) | 0.0321 (5) | |
O6A | 0.16551 (19) | 1.00919 (13) | 1.32410 (11) | 0.0328 (5) | |
O7A | 0.28554 (19) | 0.89623 (13) | 1.36991 (10) | 0.0319 (5) | |
O8A | 0.6230 (2) | 0.77922 (13) | 1.17662 (12) | 0.0390 (5) | |
O9A | 0.52325 (19) | 0.72863 (12) | 1.01930 (11) | 0.0308 (5) | |
N4A | 0.21560 (19) | 1.01815 (13) | 0.98394 (12) | 0.0201 (5) | |
N5A | 0.2416 (2) | 0.94539 (14) | 1.30886 (12) | 0.0244 (5) | |
N6A | 0.5304 (2) | 0.78063 (13) | 1.10164 (12) | 0.0234 (5) | |
C9A | 0.3699 (2) | 0.89222 (14) | 1.02956 (13) | 0.0180 (5) | |
C10A | 0.2724 (2) | 0.96016 (14) | 1.05433 (13) | 0.0180 (5) | |
C11A | 0.2308 (2) | 0.97693 (15) | 1.14328 (14) | 0.0195 (5) | |
C12A | 0.2849 (2) | 0.92743 (15) | 1.21527 (14) | 0.0204 (5) | |
C13A | 0.3819 (2) | 0.86228 (15) | 1.20011 (14) | 0.0206 (5) | |
C14A | 0.4230 (2) | 0.84649 (15) | 1.11150 (14) | 0.0195 (5) | |
O3B | 0.89240 (17) | 0.35722 (12) | 0.79658 (10) | 0.0249 (4) | |
O4B | 0.6301 (3) | 0.42205 (17) | 0.81896 (14) | 0.0529 (8) | |
O5B | 0.6586 (2) | 0.56976 (13) | 0.76979 (13) | 0.0383 (6) | |
O6B | 0.6646 (2) | 0.51986 (14) | 0.42281 (12) | 0.0448 (6) | |
O7B | 0.80575 (19) | 0.42411 (13) | 0.36653 (11) | 0.0317 (5) | |
O8B | 1.02701 (19) | 0.21778 (13) | 0.55444 (11) | 0.0312 (5) | |
O9B | 1.0651 (2) | 0.24881 (13) | 0.71314 (11) | 0.0344 (5) | |
N4B | 0.6782 (2) | 0.48144 (15) | 0.76599 (12) | 0.0265 (5) | |
N5B | 0.7496 (2) | 0.46085 (14) | 0.43269 (12) | 0.0252 (5) | |
N6B | 1.00820 (19) | 0.26385 (13) | 0.63278 (12) | 0.0227 (5) | |
C9B | 0.8564 (2) | 0.37611 (14) | 0.71299 (14) | 0.0185 (5) | |
C10B | 0.7547 (2) | 0.44294 (15) | 0.69087 (14) | 0.0198 (5) | |
C11B | 0.7238 (2) | 0.47285 (15) | 0.60319 (14) | 0.0210 (5) | |
C12B | 0.7850 (2) | 0.43321 (15) | 0.52695 (14) | 0.0205 (5) | |
C13B | 0.8778 (2) | 0.36448 (15) | 0.53866 (14) | 0.0196 (5) | |
C14B | 0.9121 (2) | 0.33741 (15) | 0.62796 (14) | 0.0192 (5) | |
H2A1 | 0.57240 | 0.70950 | 0.80760 | 0.0270* | |
H1A | 0.35820 | 0.87870 | 0.80800 | 0.0220* | |
H2A2 | 0.48630 | 0.76730 | 0.86770 | 0.0270* | |
H7A1 | 0.64610 | 0.73270 | 0.42760 | 0.0420* | |
H7A2 | 0.57880 | 0.66990 | 0.50260 | 0.0420* | |
H7A3 | 0.72390 | 0.77530 | 0.54130 | 0.0420* | |
H5A | 0.34460 | 0.91780 | 0.53790 | 0.0240* | |
H8A1 | 0.13450 | 1.07250 | 0.65450 | 0.0400* | |
H8A2 | 0.12910 | 0.97750 | 0.56990 | 0.0400* | |
H8A3 | 0.28710 | 1.07380 | 0.61340 | 0.0400* | |
H1B | 0.88700 | 0.38600 | 0.93450 | 0.0230* | |
H5B | 0.82280 | 0.41150 | 1.20380 | 0.0260* | |
H2B1 | 1.10340 | 0.21790 | 0.94230 | 0.0260* | |
H2B2 | 1.03290 | 0.28110 | 0.87910 | 0.0260* | |
H8B1 | 0.63080 | 0.56990 | 1.07660 | 0.0400* | |
H8B2 | 0.75640 | 0.56070 | 1.16600 | 0.0400* | |
H8B3 | 0.60060 | 0.46450 | 1.11550 | 0.0400* | |
H7B1 | 1.06670 | 0.19620 | 1.32750 | 0.0460* | |
H7B2 | 1.16950 | 0.24040 | 1.25620 | 0.0460* | |
H7B3 | 1.01240 | 0.14340 | 1.21380 | 0.0460* | |
H11A | 0.16710 | 1.02100 | 1.15490 | 0.0230* | |
H13A | 0.41810 | 0.83000 | 1.24940 | 0.0250* | |
H11B | 0.66240 | 0.51920 | 0.59500 | 0.0250* | |
H13B | 0.91640 | 0.33700 | 0.48640 | 0.0230* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0284 (7) | 0.0308 (8) | 0.0184 (7) | 0.0158 (6) | 0.0095 (6) | 0.0064 (6) |
O2A | 0.0285 (7) | 0.0253 (7) | 0.0198 (7) | 0.0165 (6) | 0.0087 (6) | 0.0082 (6) |
N1A | 0.0216 (8) | 0.0196 (8) | 0.0151 (7) | 0.0086 (6) | 0.0055 (6) | 0.0042 (6) |
N2A | 0.0309 (9) | 0.0240 (8) | 0.0204 (8) | 0.0168 (7) | 0.0099 (7) | 0.0092 (7) |
N3A | 0.0229 (8) | 0.0210 (8) | 0.0186 (8) | 0.0081 (7) | 0.0067 (6) | 0.0050 (6) |
C2A | 0.0185 (9) | 0.0157 (8) | 0.0201 (9) | 0.0048 (7) | 0.0044 (7) | 0.0039 (7) |
C4A | 0.0205 (9) | 0.0207 (9) | 0.0178 (9) | 0.0053 (7) | 0.0056 (7) | 0.0034 (7) |
C5A | 0.0234 (10) | 0.0214 (9) | 0.0183 (9) | 0.0091 (8) | 0.0048 (7) | 0.0064 (7) |
C6A | 0.0190 (9) | 0.0166 (9) | 0.0187 (9) | 0.0053 (7) | 0.0034 (7) | 0.0033 (7) |
C7A | 0.0309 (11) | 0.0362 (12) | 0.0239 (10) | 0.0191 (9) | 0.0118 (9) | 0.0059 (9) |
C8A | 0.0339 (11) | 0.0299 (11) | 0.0226 (10) | 0.0193 (9) | 0.0061 (9) | 0.0093 (8) |
O1B | 0.0284 (8) | 0.0339 (8) | 0.0203 (7) | 0.0145 (6) | 0.0068 (6) | 0.0120 (6) |
O2B | 0.0269 (7) | 0.0237 (7) | 0.0238 (7) | 0.0135 (6) | 0.0084 (6) | 0.0072 (6) |
N1B | 0.0225 (8) | 0.0201 (8) | 0.0172 (8) | 0.0089 (6) | 0.0059 (6) | 0.0069 (6) |
N2B | 0.0270 (9) | 0.0225 (8) | 0.0204 (8) | 0.0137 (7) | 0.0070 (7) | 0.0067 (7) |
N3B | 0.0227 (8) | 0.0239 (8) | 0.0193 (8) | 0.0086 (7) | 0.0047 (7) | 0.0064 (7) |
C2B | 0.0177 (9) | 0.0186 (9) | 0.0198 (9) | 0.0056 (7) | 0.0034 (7) | 0.0038 (7) |
C4B | 0.0198 (9) | 0.0238 (10) | 0.0183 (9) | 0.0040 (8) | 0.0025 (7) | 0.0064 (8) |
C5B | 0.0233 (10) | 0.0241 (10) | 0.0186 (9) | 0.0077 (8) | 0.0071 (8) | 0.0045 (8) |
C6B | 0.0177 (9) | 0.0165 (9) | 0.0218 (9) | 0.0032 (7) | 0.0047 (7) | 0.0031 (7) |
C7B | 0.0328 (12) | 0.0387 (12) | 0.0268 (11) | 0.0161 (10) | 0.0052 (9) | 0.0167 (10) |
C8B | 0.0286 (11) | 0.0282 (11) | 0.0290 (11) | 0.0157 (9) | 0.0104 (9) | 0.0043 (9) |
O3A | 0.0302 (7) | 0.0243 (7) | 0.0171 (6) | 0.0135 (6) | 0.0085 (6) | 0.0061 (5) |
O4A | 0.0521 (10) | 0.0445 (9) | 0.0181 (7) | 0.0312 (8) | 0.0131 (7) | 0.0128 (7) |
O5A | 0.0494 (10) | 0.0332 (8) | 0.0267 (8) | 0.0287 (8) | 0.0134 (7) | 0.0110 (6) |
O6A | 0.0399 (9) | 0.0391 (9) | 0.0255 (8) | 0.0159 (7) | 0.0165 (7) | 0.0081 (7) |
O7A | 0.0377 (9) | 0.0408 (9) | 0.0180 (7) | 0.0094 (7) | 0.0060 (6) | 0.0139 (6) |
O8A | 0.0459 (10) | 0.0406 (9) | 0.0300 (8) | 0.0262 (8) | −0.0072 (7) | 0.0041 (7) |
O9A | 0.0441 (9) | 0.0314 (8) | 0.0242 (8) | 0.0231 (7) | 0.0088 (7) | 0.0067 (6) |
N4A | 0.0225 (8) | 0.0218 (8) | 0.0187 (8) | 0.0087 (7) | 0.0061 (6) | 0.0073 (6) |
N5A | 0.0255 (9) | 0.0275 (9) | 0.0173 (8) | 0.0027 (7) | 0.0053 (7) | 0.0054 (7) |
N6A | 0.0272 (9) | 0.0205 (8) | 0.0234 (9) | 0.0096 (7) | 0.0031 (7) | 0.0067 (7) |
C9A | 0.0192 (9) | 0.0162 (8) | 0.0176 (9) | 0.0049 (7) | 0.0033 (7) | 0.0031 (7) |
C10A | 0.0198 (9) | 0.0173 (9) | 0.0168 (9) | 0.0058 (7) | 0.0021 (7) | 0.0058 (7) |
C11A | 0.0190 (9) | 0.0187 (9) | 0.0195 (9) | 0.0040 (7) | 0.0045 (7) | 0.0036 (7) |
C12A | 0.0211 (9) | 0.0219 (9) | 0.0149 (9) | 0.0013 (8) | 0.0040 (7) | 0.0038 (7) |
C13A | 0.0225 (9) | 0.0183 (9) | 0.0182 (9) | 0.0031 (7) | −0.0001 (7) | 0.0069 (7) |
C14A | 0.0224 (9) | 0.0161 (9) | 0.0199 (9) | 0.0062 (7) | 0.0038 (7) | 0.0046 (7) |
O3B | 0.0318 (8) | 0.0303 (8) | 0.0188 (7) | 0.0167 (6) | 0.0078 (6) | 0.0090 (6) |
O4B | 0.0732 (14) | 0.0752 (14) | 0.0490 (11) | 0.0519 (12) | 0.0435 (10) | 0.0388 (11) |
O5B | 0.0463 (10) | 0.0317 (9) | 0.0428 (10) | 0.0229 (8) | 0.0161 (8) | 0.0008 (7) |
O6B | 0.0776 (13) | 0.0464 (10) | 0.0266 (8) | 0.0428 (10) | 0.0118 (8) | 0.0147 (8) |
O7B | 0.0380 (9) | 0.0420 (9) | 0.0190 (7) | 0.0135 (7) | 0.0118 (6) | 0.0094 (7) |
O8B | 0.0371 (9) | 0.0359 (8) | 0.0291 (8) | 0.0220 (7) | 0.0149 (7) | 0.0054 (7) |
O9B | 0.0411 (9) | 0.0403 (9) | 0.0255 (8) | 0.0273 (8) | −0.0010 (7) | 0.0040 (7) |
N4B | 0.0292 (9) | 0.0365 (10) | 0.0190 (8) | 0.0199 (8) | 0.0054 (7) | 0.0054 (7) |
N5B | 0.0337 (10) | 0.0231 (8) | 0.0188 (8) | 0.0083 (7) | 0.0057 (7) | 0.0057 (7) |
N6B | 0.0209 (8) | 0.0231 (8) | 0.0246 (9) | 0.0090 (7) | 0.0052 (7) | 0.0039 (7) |
C9B | 0.0206 (9) | 0.0167 (9) | 0.0175 (9) | 0.0047 (7) | 0.0040 (7) | 0.0041 (7) |
C10B | 0.0223 (9) | 0.0209 (9) | 0.0175 (9) | 0.0096 (8) | 0.0052 (7) | 0.0026 (7) |
C11B | 0.0247 (10) | 0.0187 (9) | 0.0205 (9) | 0.0098 (8) | 0.0035 (8) | 0.0041 (7) |
C12B | 0.0237 (10) | 0.0198 (9) | 0.0173 (9) | 0.0059 (8) | 0.0039 (7) | 0.0047 (7) |
C13B | 0.0195 (9) | 0.0183 (9) | 0.0194 (9) | 0.0032 (7) | 0.0066 (7) | 0.0024 (7) |
C14B | 0.0190 (9) | 0.0183 (9) | 0.0222 (9) | 0.0082 (7) | 0.0059 (7) | 0.0045 (7) |
Geometric parameters (Å, º) top
O1A—C4A | 1.327 (2) | N5A—C12A | 1.444 (3) |
O1A—C7A | 1.440 (3) | N6A—C14A | 1.462 (3) |
O2A—C6A | 1.317 (2) | N4B—C10B | 1.454 (3) |
O2A—C8A | 1.448 (3) | N5B—C12B | 1.443 (3) |
O1B—C7B | 1.445 (3) | N6B—C14B | 1.457 (3) |
O1B—C4B | 1.328 (2) | C4A—C5A | 1.397 (3) |
O2B—C6B | 1.321 (2) | C5A—C6A | 1.363 (3) |
O2B—C8B | 1.447 (3) | C5A—H5A | 0.9300 |
O3A—C9A | 1.251 (2) | C7A—H7A2 | 0.9600 |
O4A—N4A | 1.221 (2) | C7A—H7A1 | 0.9600 |
O5A—N4A | 1.233 (2) | C7A—H7A3 | 0.9600 |
O6A—N5A | 1.229 (3) | C8A—H8A3 | 0.9600 |
O7A—N5A | 1.234 (2) | C8A—H8A1 | 0.9600 |
O8A—N6A | 1.221 (2) | C8A—H8A2 | 0.9600 |
O9A—N6A | 1.230 (2) | C4B—C5B | 1.400 (3) |
O3B—C9B | 1.251 (2) | C5B—C6B | 1.362 (3) |
O4B—N4B | 1.229 (3) | C5B—H5B | 0.9300 |
O5B—N4B | 1.224 (3) | C7B—H7B3 | 0.9600 |
O6B—N5B | 1.229 (3) | C7B—H7B2 | 0.9600 |
O7B—N5B | 1.227 (2) | C7B—H7B1 | 0.9600 |
O8B—N6B | 1.233 (2) | C8B—H8B3 | 0.9600 |
O9B—N6B | 1.226 (2) | C8B—H8B2 | 0.9600 |
N1A—C2A | 1.362 (3) | C8B—H8B1 | 0.9600 |
N1A—C6A | 1.367 (2) | C9A—C14A | 1.456 (3) |
N2A—C2A | 1.324 (3) | C9A—C10A | 1.449 (3) |
N3A—C4A | 1.329 (3) | C10A—C11A | 1.374 (3) |
N3A—C2A | 1.336 (3) | C11A—C12A | 1.382 (3) |
N1A—H1A | 0.8600 | C12A—C13A | 1.389 (3) |
N2A—H2A1 | 0.8600 | C13A—C14A | 1.366 (3) |
N2A—H2A2 | 0.8600 | C11A—H11A | 0.9300 |
N1B—C6B | 1.365 (3) | C13A—H13A | 0.9300 |
N1B—C2B | 1.366 (3) | C9B—C10B | 1.452 (3) |
N2B—C2B | 1.321 (3) | C9B—C14B | 1.448 (3) |
N3B—C2B | 1.335 (3) | C10B—C11B | 1.367 (3) |
N3B—C4B | 1.328 (3) | C11B—C12B | 1.381 (3) |
N1B—H1B | 0.8600 | C12B—C13B | 1.390 (3) |
N2B—H2B1 | 0.8600 | C13B—C14B | 1.373 (3) |
N2B—H2B2 | 0.8600 | C11B—H11B | 0.9300 |
N4A—C10A | 1.455 (2) | C13B—H13B | 0.9300 |
| | | |
O1A···O7Ai | 3.135 (2) | N3A···H7A2 | 2.5800 |
O1B···N1Aii | 3.238 (2) | N3B···H7B3 | 2.6000 |
O1B···O7Biii | 3.120 (2) | N3B···H7B2 | 2.6100 |
O2A···O8Aiv | 3.228 (2) | C2A···O3A | 3.178 (2) |
O2A···C7Bii | 3.351 (3) | C2A···O7Bviii | 3.206 (3) |
O2A···O4A | 2.792 (2) | C2A···C11Aiv | 3.364 (3) |
O2A···C13Aiv | 3.315 (2) | C2B···C10Aii | 3.485 (3) |
O2B···O4B | 2.971 (2) | C2B···C14Aii | 3.591 (3) |
O2B···C2Bv | 3.392 (2) | C2B···O2Bv | 3.392 (2) |
O2B···O9Aii | 3.102 (2) | C2B···C9Aii | 3.415 (3) |
O2B···N1Bv | 3.242 (2) | C2B···O3B | 3.211 (2) |
O3A···O4A | 2.649 (2) | C4A···C13Bviii | 3.353 (3) |
O3A···C2A | 3.178 (2) | C4A···C12Bviii | 3.442 (3) |
O3A···N2A | 2.771 (2) | C4A···O6Aiv | 3.294 (3) |
O3A···O9A | 2.683 (2) | C4A···N5Aiv | 3.364 (3) |
O3A···N1A | 2.720 (2) | C4B···O5Bv | 3.292 (3) |
O3A···C10Aiv | 3.093 (2) | C4B···O3Aii | 3.402 (2) |
O3A···N4A | 2.903 (2) | C5A···O7Ai | 3.100 (2) |
O3A···N6A | 2.867 (2) | C5A···N5Aiv | 3.409 (3) |
O3A···O3Aiv | 3.188 (2) | C5A···C13Bviii | 3.487 (3) |
O3A···N4Aiv | 3.143 (2) | C5B···O7Biii | 3.142 (2) |
O3A···C4Bii | 3.402 (2) | C5B···C9Bv | 3.467 (3) |
O3A···C9Aiv | 3.111 (2) | C6A···C12Aiv | 3.401 (3) |
O3B···C13Aii | 3.291 (3) | C6A···C13Aiv | 3.332 (3) |
O3B···N4B | 2.846 (2) | C6B···O3Bv | 3.365 (2) |
O3B···N2B | 2.842 (2) | C6B···O9Aii | 3.165 (3) |
O3B···C6Bv | 3.365 (2) | C7A···O8Bix | 3.205 (3) |
O3B···N1B | 2.707 (2) | C7A···O6B | 3.050 (3) |
O3B···N6B | 2.920 (2) | C7A···C11Bviii | 3.462 (3) |
O3B···C2B | 3.211 (2) | C7B···O4Aii | 3.346 (3) |
O3B···O4B | 2.737 (3) | C7B···O6Ax | 3.232 (3) |
O3B···O9B | 2.657 (2) | C7B···O2Aii | 3.351 (3) |
O4A···O2A | 2.792 (2) | C8A···O6Avi | 3.322 (3) |
O4A···N6Aiv | 3.195 (2) | C8A···O8Aiv | 3.238 (3) |
O4A···C9Aiv | 3.400 (3) | C8B···N2Bv | 3.422 (3) |
O4A···C14Aiv | 3.326 (3) | C8B···O9Aii | 3.338 (3) |
O4A···O3A | 2.649 (2) | C8B···O4Bii | 3.356 (4) |
O4A···N1A | 3.226 (2) | C9A···C9Aiv | 3.511 (3) |
O4A···C7Bii | 3.346 (3) | C9A···C2Bii | 3.415 (3) |
O4B···O8Aii | 3.030 (3) | C9A···O4Aiv | 3.400 (3) |
O4B···O3B | 2.737 (3) | C9A···O3Aiv | 3.111 (2) |
O4B···O2B | 2.971 (2) | C9B···C5Bv | 3.467 (3) |
O4B···C8Bii | 3.356 (4) | C9B···O7Aii | 3.418 (2) |
O4B···N6Aii | 3.189 (3) | C10A···O3Aiv | 3.093 (2) |
O5A···O5Avi | 3.128 (2) | C10A···C2Bii | 3.485 (3) |
O5A···N2Bvii | 3.017 (2) | C11A···N2Bii | 3.336 (3) |
O5A···N3Bvii | 3.136 (2) | C11A···C2Aiv | 3.364 (3) |
O5B···C4Bv | 3.292 (3) | C11A···N1Aiv | 3.413 (3) |
O5B···N2A | 3.047 (3) | C11B···C7Aviii | 3.462 (3) |
O5B···N3Bv | 3.168 (2) | C12A···N2Bii | 3.399 (3) |
O6A···C7Bvii | 3.232 (3) | C12A···N1Aiv | 3.370 (3) |
O6A···C4Aiv | 3.294 (3) | C12A···C6Aiv | 3.401 (3) |
O6A···C8Avi | 3.322 (3) | C12B···C4Aviii | 3.442 (3) |
O6B···C7A | 3.050 (3) | C13A···C6Aiv | 3.332 (3) |
O7A···C5Aiii | 3.100 (2) | C13A···O3Bii | 3.291 (3) |
O7A···N6Bii | 2.894 (2) | C13A···O2Aiv | 3.315 (2) |
O7A···O9Bii | 3.087 (2) | C13B···C4Aviii | 3.353 (3) |
O7A···O1Aiii | 3.135 (2) | C13B···O7Bix | 3.284 (3) |
O7A···C14Bii | 3.151 (3) | C13B···N5Bix | 3.417 (3) |
O7A···C9Bii | 3.418 (2) | C13B···C5Aviii | 3.487 (3) |
O7B···O1Bi | 3.120 (2) | C14A···O4Aiv | 3.326 (3) |
O7B···C5Bi | 3.142 (2) | C14A···C2Bii | 3.591 (3) |
O7B···C2Aviii | 3.206 (3) | C14A···N1Bii | 3.374 (3) |
O7B···C13Bix | 3.284 (3) | C14B···O7Aii | 3.151 (3) |
O8A···O2Aiv | 3.228 (2) | C5A···H8A3 | 2.7600 |
O8A···O4Bii | 3.030 (3) | C5A···H8A2 | 2.7500 |
O8A···O9Bv | 3.061 (3) | C5B···H8B2 | 2.7400 |
O8A···C8Aiv | 3.238 (3) | C5B···H8B3 | 2.8100 |
O8B···C7Aix | 3.205 (3) | C7B···H7A3v | 3.0000 |
O9A···C6Bii | 3.165 (3) | C8A···H5A | 2.5700 |
O9A···N2A | 2.970 (2) | C8B···H5B | 2.6000 |
O9A···C8Bii | 3.338 (3) | C8B···H2B2v | 3.0700 |
O9A···O3A | 2.683 (2) | C9A···H1A | 3.0900 |
O9A···O2Bii | 3.102 (2) | C9A···H2A2 | 3.0900 |
O9B···O8Av | 3.061 (3) | C9B···H1B | 3.0700 |
O9B···N5Aii | 3.150 (3) | C11B···H7A2viii | 2.8200 |
O9B···O3B | 2.657 (2) | C12B···H7A2viii | 3.0800 |
O9B···O7Aii | 3.087 (2) | H2A1···O5B | 2.2100 |
O9B···N2B | 3.134 (2) | H2A1···H7B2v | 2.5900 |
O3A···H2A2 | 2.0300 | H1A···H2A2 | 2.2700 |
O3A···H1A | 1.9700 | H1A···O3A | 1.9700 |
O3B···H2B2 | 2.1100 | H1A···C9A | 3.0900 |
O3B···H1B | 1.9300 | H1A···O4A | 2.5100 |
O4A···H7B3ii | 2.4700 | H1B···H2B2 | 2.2800 |
O4A···H1A | 2.5100 | H1B···O3B | 1.9300 |
O4B···H1B | 2.7500 | H1B···O4B | 2.7500 |
O5A···H2B1vii | 2.2400 | H1B···C9B | 3.0700 |
O5A···H11A | 2.3300 | H2A2···O9A | 2.2700 |
O5B···H7B2v | 2.7100 | H2A2···C9A | 3.0900 |
O5B···H2A1 | 2.2100 | H2A2···O3A | 2.0300 |
O5B···H11B | 2.4600 | H2A2···H1A | 2.2700 |
O6A···H7B1vii | 2.8400 | H7A1···O8Bix | 2.7600 |
O6A···H11A | 2.4300 | H7A1···O6B | 2.8600 |
O6A···H8A1vi | 2.7000 | H7A2···C11Bviii | 2.8200 |
O6B···H7A1 | 2.8600 | H7A2···N3A | 2.5800 |
O6B···H7A2 | 2.4800 | H7A2···O6B | 2.4800 |
O6B···H11Bviii | 2.7700 | H7A2···C12Bviii | 3.0800 |
O6B···H11B | 2.4400 | H7A3···O8Bix | 2.7900 |
O7A···H5Aiii | 2.2900 | H7A3···N3A | 2.6500 |
O7A···H13A | 2.4200 | H7A3···H7B1v | 2.2700 |
O7B···H5Bi | 2.3100 | H7A3···C7Bv | 3.0000 |
O7B···H13B | 2.4100 | H5A···H8A2 | 2.3400 |
O8A···H13A | 2.4300 | H5A···H8A3 | 2.3900 |
O8A···H8A1iv | 2.9100 | H5A···C8A | 2.5700 |
O8B···H13B | 2.3200 | H5A···O7Ai | 2.2900 |
O8B···H7A1ix | 2.7600 | H5B···C8B | 2.6000 |
O8B···H8A1x | 2.8300 | H5B···O7Biii | 2.3100 |
O8B···H8A2viii | 2.7200 | H5B···H8B3 | 2.4600 |
O8B···H7A3ix | 2.7900 | H5B···H8B2 | 2.3300 |
O9A···H8B3ii | 2.7400 | H8A1···O8Bvii | 2.8300 |
O9A···H8B1 | 2.7100 | H8A1···O9Bvii | 2.6100 |
O9A···H2A2 | 2.2700 | H8A1···O8Aiv | 2.9100 |
O9B···H8A1x | 2.6100 | H8A1···O6Avi | 2.7000 |
O9B···H2B2 | 2.4000 | H8A2···O8Bviii | 2.7200 |
O9B···H8B2v | 2.7000 | H8A2···H5A | 2.3400 |
N1A···C12Aiv | 3.370 (3) | H8A2···C5A | 2.7500 |
N1A···O4A | 3.226 (2) | H8A3···H5A | 2.3900 |
N1A···O1Bii | 3.238 (2) | H8A3···C5A | 2.7600 |
N1A···O3A | 2.720 (2) | H2B1···O5Ax | 2.2400 |
N1A···C11Aiv | 3.413 (3) | H2B2···H1B | 2.2800 |
N1B···O3B | 2.707 (2) | H2B2···C8Bv | 3.0700 |
N1B···C14Aii | 3.374 (3) | H2B2···O3B | 2.1100 |
N1B···O2Bv | 3.242 (2) | H2B2···O9B | 2.4000 |
N2A···O5B | 3.047 (3) | H8B1···O9A | 2.7100 |
N2A···O9A | 2.970 (2) | H11A···O5A | 2.3300 |
N2A···O3A | 2.771 (2) | H11A···O6A | 2.4300 |
N2B···C11Aii | 3.336 (3) | H11A···H7B3vii | 2.5200 |
N2B···C12Aii | 3.399 (3) | H11B···O6Bviii | 2.7700 |
N2B···O5Ax | 3.017 (2) | H11B···O5B | 2.4600 |
N2B···O9B | 3.134 (2) | H11B···O6B | 2.4400 |
N2B···C8Bv | 3.422 (3) | H8B2···C5B | 2.7400 |
N2B···O3B | 2.842 (2) | H8B2···H5B | 2.3300 |
N3A···N5Bviii | 3.254 (2) | H8B2···O9Bv | 2.7000 |
N3B···O5Ax | 3.136 (2) | H8B3···O9Aii | 2.7400 |
N3B···O5Bv | 3.168 (2) | H8B3···H5B | 2.4600 |
N4A···O3A | 2.903 (2) | H8B3···C5B | 2.8100 |
N4A···O3Aiv | 3.143 (2) | H13A···O8A | 2.4300 |
N4B···O3B | 2.846 (2) | H13A···O7A | 2.4200 |
N5A···C4Aiv | 3.364 (3) | H13B···O7B | 2.4100 |
N5A···O9Bii | 3.150 (3) | H13B···O8B | 2.3200 |
N5A···C5Aiv | 3.409 (3) | H7B1···O6Ax | 2.8400 |
N5B···C13Bix | 3.417 (3) | H7B1···H7A3v | 2.2700 |
N5B···N3Aviii | 3.254 (2) | H7B2···O5Bv | 2.7100 |
N6A···O4Bii | 3.189 (3) | H7B2···N3Av | 2.8800 |
N6A···O4Aiv | 3.195 (2) | H7B2···H2A1v | 2.5900 |
N6A···O3A | 2.867 (2) | H7B2···N3B | 2.6100 |
N6B···O7Aii | 2.894 (2) | H7B3···H11Ax | 2.5200 |
N6B···O3B | 2.920 (2) | H7B3···O4Aii | 2.4700 |
N3A···H7B2v | 2.8800 | H7B3···N3B | 2.6000 |
N3A···H7A3 | 2.6500 | | |
| | | |
C4A—O1A—C7A | 118.07 (16) | N1B—C2B—N3B | 122.09 (17) |
C6A—O2A—C8A | 116.82 (16) | N1B—C2B—N2B | 118.18 (17) |
C4B—O1B—C7B | 118.15 (16) | N2B—C2B—N3B | 119.73 (18) |
C6B—O2B—C8B | 117.07 (16) | O1B—C4B—N3B | 119.22 (18) |
C2A—N1A—C6A | 120.27 (16) | N3B—C4B—C5B | 125.39 (18) |
C2A—N3A—C4A | 116.36 (17) | O1B—C4B—C5B | 115.39 (17) |
C2A—N1A—H1A | 120.00 | C4B—C5B—C6B | 115.91 (17) |
C6A—N1A—H1A | 120.00 | N1B—C6B—C5B | 119.72 (18) |
C2A—N2A—H2A1 | 120.00 | O2B—C6B—C5B | 128.18 (18) |
C2A—N2A—H2A2 | 120.00 | O2B—C6B—N1B | 112.10 (16) |
H2A1—N2A—H2A2 | 120.00 | C6B—C5B—H5B | 122.00 |
C2B—N1B—C6B | 120.44 (16) | C4B—C5B—H5B | 122.00 |
C2B—N3B—C4B | 116.42 (18) | H7B1—C7B—H7B2 | 109.00 |
C6B—N1B—H1B | 120.00 | H7B2—C7B—H7B3 | 109.00 |
C2B—N1B—H1B | 120.00 | O1B—C7B—H7B1 | 109.00 |
C2B—N2B—H2B1 | 120.00 | O1B—C7B—H7B2 | 109.00 |
H2B1—N2B—H2B2 | 120.00 | H7B1—C7B—H7B3 | 110.00 |
C2B—N2B—H2B2 | 120.00 | O1B—C7B—H7B3 | 109.00 |
O4A—N4A—O5A | 122.05 (17) | O2B—C8B—H8B1 | 109.00 |
O4A—N4A—C10A | 120.06 (17) | O2B—C8B—H8B2 | 110.00 |
O5A—N4A—C10A | 117.88 (16) | H8B1—C8B—H8B3 | 109.00 |
O6A—N5A—C12A | 118.81 (17) | H8B2—C8B—H8B3 | 109.00 |
O6A—N5A—O7A | 123.62 (17) | O2B—C8B—H8B3 | 109.00 |
O7A—N5A—C12A | 117.57 (17) | H8B1—C8B—H8B2 | 109.00 |
O8A—N6A—C14A | 117.93 (17) | C10A—C9A—C14A | 111.85 (16) |
O8A—N6A—O9A | 122.85 (19) | O3A—C9A—C10A | 124.91 (17) |
O9A—N6A—C14A | 119.23 (17) | O3A—C9A—C14A | 123.19 (17) |
O4B—N4B—O5B | 123.5 (2) | N4A—C10A—C11A | 115.75 (17) |
O4B—N4B—C10B | 118.6 (2) | C9A—C10A—C11A | 124.16 (17) |
O5B—N4B—C10B | 117.79 (18) | N4A—C10A—C9A | 120.06 (16) |
O6B—N5B—C12B | 118.27 (17) | C10A—C11A—C12A | 119.15 (18) |
O7B—N5B—C12B | 118.31 (17) | N5A—C12A—C13A | 119.39 (17) |
O6B—N5B—O7B | 123.42 (18) | C11A—C12A—C13A | 121.49 (18) |
O8B—N6B—O9B | 122.55 (18) | N5A—C12A—C11A | 119.12 (17) |
O9B—N6B—C14B | 119.59 (17) | C12A—C13A—C14A | 118.85 (18) |
O8B—N6B—C14B | 117.86 (16) | C9A—C14A—C13A | 124.46 (18) |
N1A—C2A—N2A | 117.92 (17) | N6A—C14A—C13A | 116.17 (17) |
N1A—C2A—N3A | 122.45 (17) | N6A—C14A—C9A | 119.36 (16) |
N2A—C2A—N3A | 119.63 (18) | C10A—C11A—H11A | 120.00 |
O1A—C4A—N3A | 119.61 (17) | C12A—C11A—H11A | 120.00 |
O1A—C4A—C5A | 115.34 (17) | C14A—C13A—H13A | 121.00 |
N3A—C4A—C5A | 125.05 (18) | C12A—C13A—H13A | 121.00 |
C4A—C5A—C6A | 116.34 (17) | O3B—C9B—C10B | 123.01 (17) |
N1A—C6A—C5A | 119.50 (17) | O3B—C9B—C14B | 125.19 (18) |
O2A—C6A—C5A | 127.78 (18) | C10B—C9B—C14B | 111.79 (16) |
O2A—C6A—N1A | 112.72 (16) | N4B—C10B—C9B | 118.81 (17) |
C6A—C5A—H5A | 122.00 | N4B—C10B—C11B | 116.48 (17) |
C4A—C5A—H5A | 122.00 | C9B—C10B—C11B | 124.71 (17) |
O1A—C7A—H7A1 | 109.00 | C10B—C11B—C12B | 119.03 (18) |
H7A1—C7A—H7A2 | 109.00 | N5B—C12B—C11B | 120.02 (17) |
O1A—C7A—H7A2 | 110.00 | N5B—C12B—C13B | 119.01 (17) |
H7A2—C7A—H7A3 | 109.00 | C11B—C12B—C13B | 120.95 (18) |
O1A—C7A—H7A3 | 109.00 | C12B—C13B—C14B | 119.57 (18) |
H7A1—C7A—H7A3 | 109.00 | N6B—C14B—C9B | 120.55 (16) |
O2A—C8A—H8A2 | 109.00 | N6B—C14B—C13B | 115.63 (17) |
O2A—C8A—H8A3 | 110.00 | C9B—C14B—C13B | 123.81 (18) |
H8A1—C8A—H8A3 | 109.00 | C10B—C11B—H11B | 120.00 |
H8A2—C8A—H8A3 | 110.00 | C12B—C11B—H11B | 121.00 |
O2A—C8A—H8A1 | 109.00 | C12B—C13B—H13B | 120.00 |
H8A1—C8A—H8A2 | 109.00 | C14B—C13B—H13B | 120.00 |
| | | |
C7A—O1A—C4A—N3A | −6.2 (3) | O8B—N6B—C14B—C9B | 166.64 (18) |
C7A—O1A—C4A—C5A | 174.24 (18) | O8B—N6B—C14B—C13B | −12.3 (3) |
C8A—O2A—C6A—N1A | 177.91 (17) | O9B—N6B—C14B—C13B | 168.64 (18) |
C8A—O2A—C6A—C5A | −1.3 (3) | O9B—N6B—C14B—C9B | −12.4 (3) |
C7B—O1B—C4B—C5B | −178.73 (18) | O1A—C4A—C5A—C6A | −178.55 (17) |
C7B—O1B—C4B—N3B | 1.1 (3) | N3A—C4A—C5A—C6A | 2.0 (3) |
C8B—O2B—C6B—N1B | 174.40 (17) | C4A—C5A—C6A—N1A | −0.6 (3) |
C8B—O2B—C6B—C5B | −6.3 (3) | C4A—C5A—C6A—O2A | 178.61 (19) |
C6A—N1A—C2A—N3A | 1.5 (3) | O1B—C4B—C5B—C6B | −179.02 (18) |
C2A—N1A—C6A—O2A | 179.66 (16) | N3B—C4B—C5B—C6B | 1.2 (3) |
C2A—N1A—C6A—C5A | −1.0 (3) | C4B—C5B—C6B—N1B | 0.0 (3) |
C6A—N1A—C2A—N2A | −179.05 (17) | C4B—C5B—C6B—O2B | −179.27 (19) |
C4A—N3A—C2A—N1A | −0.3 (3) | O3A—C9A—C10A—N4A | −1.2 (3) |
C4A—N3A—C2A—N2A | −179.68 (18) | O3A—C9A—C14A—C13A | 179.79 (19) |
C2A—N3A—C4A—O1A | 179.01 (17) | C10A—C9A—C14A—N6A | −176.52 (16) |
C2A—N3A—C4A—C5A | −1.5 (3) | C10A—C9A—C14A—C13A | 2.1 (3) |
C6B—N1B—C2B—N2B | −179.02 (18) | O3A—C9A—C10A—C11A | −179.48 (19) |
C6B—N1B—C2B—N3B | 1.3 (3) | C14A—C9A—C10A—N4A | 176.45 (16) |
C2B—N1B—C6B—O2B | 178.21 (17) | C14A—C9A—C10A—C11A | −1.9 (3) |
C2B—N1B—C6B—C5B | −1.2 (3) | O3A—C9A—C14A—N6A | 1.2 (3) |
C2B—N3B—C4B—C5B | −1.1 (3) | N4A—C10A—C11A—C12A | −177.85 (17) |
C4B—N3B—C2B—N1B | −0.2 (3) | C9A—C10A—C11A—C12A | 0.5 (3) |
C4B—N3B—C2B—N2B | −179.86 (18) | C10A—C11A—C12A—N5A | 179.79 (18) |
C2B—N3B—C4B—O1B | 179.13 (18) | C10A—C11A—C12A—C13A | 0.8 (3) |
O5A—N4A—C10A—C11A | 12.5 (3) | N5A—C12A—C13A—C14A | −179.54 (18) |
O5A—N4A—C10A—C9A | −165.94 (18) | C11A—C12A—C13A—C14A | −0.6 (3) |
O4A—N4A—C10A—C11A | −168.31 (18) | C12A—C13A—C14A—C9A | −1.0 (3) |
O4A—N4A—C10A—C9A | 13.2 (3) | C12A—C13A—C14A—N6A | 177.66 (17) |
O6A—N5A—C12A—C11A | −4.2 (3) | O3B—C9B—C10B—N4B | −6.2 (3) |
O7A—N5A—C12A—C11A | 176.75 (18) | O3B—C9B—C10B—C11B | 174.15 (19) |
O6A—N5A—C12A—C13A | 174.82 (19) | C14B—C9B—C10B—N4B | 175.18 (17) |
O7A—N5A—C12A—C13A | −4.3 (3) | C14B—C9B—C10B—C11B | −4.5 (3) |
O9A—N6A—C14A—C9A | −29.8 (3) | O3B—C9B—C14B—N6B | 5.0 (3) |
O8A—N6A—C14A—C13A | −28.0 (3) | O3B—C9B—C14B—C13B | −176.17 (19) |
O9A—N6A—C14A—C13A | 151.42 (19) | C10B—C9B—C14B—N6B | −176.42 (17) |
O8A—N6A—C14A—C9A | 150.80 (19) | C10B—C9B—C14B—C13B | 2.5 (3) |
O4B—N4B—C10B—C11B | 143.1 (2) | N4B—C10B—C11B—C12B | −175.99 (18) |
O4B—N4B—C10B—C9B | −36.6 (3) | C9B—C10B—C11B—C12B | 3.7 (3) |
O5B—N4B—C10B—C9B | 146.74 (19) | C10B—C11B—C12B—N5B | 177.97 (18) |
O5B—N4B—C10B—C11B | −33.5 (3) | C10B—C11B—C12B—C13B | −0.5 (3) |
O6B—N5B—C12B—C13B | 178.48 (19) | N5B—C12B—C13B—C14B | −179.89 (18) |
O7B—N5B—C12B—C11B | −179.90 (19) | C11B—C12B—C13B—C14B | −1.4 (3) |
O6B—N5B—C12B—C11B | 0.0 (3) | C12B—C13B—C14B—N6B | 179.19 (17) |
O7B—N5B—C12B—C13B | −1.4 (3) | C12B—C13B—C14B—C9B | 0.3 (3) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+2; (iii) x, y, z+1; (iv) −x+1, −y+2, −z+2; (v) −x+2, −y+1, −z+2; (vi) −x, −y+2, −z+2; (vii) x−1, y+1, z; (viii) −x+1, −y+1, −z+1; (ix) −x+2, −y+1, −z+1; (x) x+1, y−1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A1···O5B | 0.86 | 2.21 | 3.047 (3) | 165 |
N1A—H1A···O3A | 0.86 | 1.97 | 2.720 (2) | 145 |
N1A—H1A···O4A | 0.86 | 2.51 | 3.226 (2) | 142 |
N1B—H1B···O3B | 0.86 | 1.93 | 2.707 (2) | 149 |
N2A—H2A2···O3A | 0.86 | 2.03 | 2.771 (2) | 143 |
N2A—H2A2···O9A | 0.86 | 2.27 | 2.970 (2) | 138 |
N2B—H2B1···O5Ax | 0.86 | 2.24 | 3.017 (2) | 151 |
N2B—H2B2···O3B | 0.86 | 2.11 | 2.842 (2) | 142 |
N2B—H2B2···O9B | 0.86 | 2.40 | 3.134 (2) | 144 |
C7A—H7A2···O6B | 0.96 | 2.48 | 3.050 (3) | 118 |
C5A—H5A···O7Ai | 0.93 | 2.29 | 3.100 (2) | 146 |
C5B—H5B···O7Biii | 0.93 | 2.31 | 3.142 (2) | 148 |
C13B—H13B···O8B | 0.93 | 2.32 | 2.643 (3) | 100 |
C7B—H7B3···O4Aii | 0.96 | 2.47 | 3.346 (3) | 152 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+2; (iii) x, y, z+1; (x) x+1, y−1, z. |
(II) 2,4-diamino-5-(4-chlorophenyl)-6-ethylpyrimidin-1-ium 2,4,6-trinitrophenolate
dimethyl sulfoxide solvate
top
Crystal data top
C12H14ClN4+·C6H2N3O7−·C2H6OS | Z = 2 |
Mr = 555.97 | F(000) = 576 |
Triclinic, P1 | Dx = 1.488 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3365 (3) Å | Cell parameters from 5230 reflections |
b = 11.1245 (3) Å | θ = 4.7–32.5° |
c = 13.1861 (6) Å | µ = 0.30 mm−1 |
α = 83.779 (3)° | T = 200 K |
β = 86.057 (3)° | Thin plate, yellow |
γ = 65.784 (3)° | 0.47 × 0.26 × 0.21 mm |
V = 1241.24 (8) Å3 | |
Data collection top
Oxford Diffraction Gemini diffractometer | 7722 independent reflections |
Radiation source: fine-focus sealed tube | 3648 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.5°, θmin = 4.7° |
ϕ and ω scans | h = −13→14 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −16→16 |
Tmin = 0.873, Tmax = 0.940 | l = −18→18 |
17314 measured reflections | |
Refinement top
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0964P)2] where P = (Fo2 + 2Fc2)/3 |
7722 reflections | (Δ/σ)max < 0.001 |
337 parameters | Δρmax = 1.09 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
Crystal data top
C12H14ClN4+·C6H2N3O7−·C2H6OS | γ = 65.784 (3)° |
Mr = 555.97 | V = 1241.24 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.3365 (3) Å | Mo Kα radiation |
b = 11.1245 (3) Å | µ = 0.30 mm−1 |
c = 13.1861 (6) Å | T = 200 K |
α = 83.779 (3)° | 0.47 × 0.26 × 0.21 mm |
β = 86.057 (3)° | |
Data collection top
Oxford Diffraction Gemini diffractometer | 7722 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 3648 reflections with I > 2σ(I) |
Tmin = 0.873, Tmax = 0.940 | Rint = 0.029 |
17314 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.172 | H-atom parameters constrained |
S = 0.93 | Δρmax = 1.09 e Å−3 |
7722 reflections | Δρmin = −0.60 e Å−3 |
337 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su'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 | x | y | z | Uiso*/Ueq | |
Cl1 | −0.49545 (10) | 1.25570 (7) | 1.03419 (6) | 0.0741 (3) | |
N1 | 0.04367 (19) | 0.65153 (14) | 0.68692 (13) | 0.0300 (5) | |
N2 | 0.1285 (2) | 0.62637 (15) | 0.51928 (14) | 0.0354 (5) | |
N3 | 0.01798 (18) | 0.83630 (14) | 0.57234 (12) | 0.0267 (5) | |
N4 | −0.1031 (2) | 1.04340 (15) | 0.62414 (14) | 0.0350 (5) | |
C2 | 0.0633 (2) | 0.70600 (17) | 0.59243 (16) | 0.0280 (6) | |
C4 | −0.0571 (2) | 0.91427 (17) | 0.64708 (15) | 0.0263 (6) | |
C5 | −0.0888 (2) | 0.86338 (17) | 0.74662 (15) | 0.0274 (6) | |
C6 | −0.0322 (2) | 0.72887 (18) | 0.76506 (16) | 0.0288 (6) | |
C7 | −0.0394 (3) | 0.65738 (19) | 0.86671 (17) | 0.0367 (7) | |
C8 | 0.1217 (4) | 0.5947 (3) | 0.9150 (2) | 0.0603 (10) | |
C9 | −0.1858 (2) | 0.95619 (17) | 0.82243 (16) | 0.0288 (6) | |
C10 | −0.3450 (3) | 0.9860 (2) | 0.83238 (18) | 0.0391 (7) | |
C11 | −0.4400 (3) | 1.0766 (2) | 0.89940 (19) | 0.0450 (8) | |
C12 | −0.3751 (3) | 1.1391 (2) | 0.95326 (18) | 0.0417 (7) | |
C13 | −0.2182 (3) | 1.1117 (2) | 0.94463 (18) | 0.0426 (8) | |
C14 | −0.1241 (3) | 1.0199 (2) | 0.87874 (17) | 0.0364 (7) | |
O1 | 0.1807 (2) | 0.38568 (13) | 0.63821 (13) | 0.0454 (5) | |
O2 | 0.2569 (2) | 0.37218 (15) | 0.44071 (14) | 0.0606 (7) | |
O3 | 0.33344 (18) | 0.18669 (15) | 0.37755 (13) | 0.0432 (5) | |
O4 | 0.37476 (19) | −0.20571 (14) | 0.56383 (15) | 0.0497 (6) | |
O5 | 0.3080 (2) | −0.21088 (15) | 0.72474 (16) | 0.0564 (7) | |
O6 | 0.1320 (3) | 0.17625 (18) | 0.89968 (16) | 0.0745 (8) | |
O7 | 0.0568 (4) | 0.36318 (19) | 0.81994 (19) | 0.1141 (12) | |
N5 | 0.2881 (2) | 0.25411 (16) | 0.45062 (15) | 0.0356 (6) | |
N6 | 0.3286 (2) | −0.15297 (17) | 0.64315 (18) | 0.0432 (7) | |
N7 | 0.1278 (2) | 0.24445 (18) | 0.82258 (16) | 0.0455 (7) | |
C15 | 0.2111 (2) | 0.26641 (18) | 0.63843 (17) | 0.0319 (6) | |
C16 | 0.2716 (2) | 0.18969 (18) | 0.54984 (17) | 0.0310 (6) | |
C17 | 0.3082 (2) | 0.05632 (18) | 0.55230 (18) | 0.0332 (6) | |
C18 | 0.2924 (2) | −0.01241 (18) | 0.64287 (19) | 0.0350 (7) | |
C19 | 0.2366 (2) | 0.05040 (19) | 0.73040 (18) | 0.0354 (7) | |
C20 | 0.1952 (2) | 0.18444 (18) | 0.72822 (17) | 0.0336 (6) | |
S1 | 0.37172 (8) | 0.63702 (5) | 0.26014 (5) | 0.0498 (2) | |
O8 | 0.2139 (2) | 0.70534 (14) | 0.31069 (13) | 0.0484 (5) | |
C21 | 0.4995 (4) | 0.5393 (3) | 0.3597 (2) | 0.0635 (10) | |
C22 | 0.3608 (4) | 0.5051 (3) | 0.2014 (3) | 0.0711 (11) | |
H1 | 0.08030 | 0.56490 | 0.69840 | 0.0360* | |
H2A | 0.14190 | 0.65930 | 0.45740 | 0.0420* | |
H2B | 0.15850 | 0.54040 | 0.53240 | 0.0420* | |
H4A | −0.08390 | 1.07380 | 0.56260 | 0.0420* | |
H4B | −0.15270 | 1.09870 | 0.67040 | 0.0420* | |
H7A | −0.07660 | 0.58760 | 0.85830 | 0.0440* | |
H7B | −0.11540 | 0.72020 | 0.91240 | 0.0440* | |
H8A | 0.19370 | 0.52470 | 0.87420 | 0.0900* | |
H8B | 0.11190 | 0.55680 | 0.98440 | 0.0900* | |
H8C | 0.16290 | 0.66240 | 0.91750 | 0.0900* | |
H10 | −0.38980 | 0.94420 | 0.79300 | 0.0470* | |
H11 | −0.54860 | 1.09470 | 0.90760 | 0.0540* | |
H13 | −0.17430 | 1.15500 | 0.98320 | 0.0510* | |
H14 | −0.01510 | 1.00070 | 0.87230 | 0.0440* | |
H17 | 0.34430 | 0.01180 | 0.49200 | 0.0400* | |
H19 | 0.22660 | 0.00150 | 0.79220 | 0.0420* | |
H21A | 0.50960 | 0.59740 | 0.40700 | 0.0950* | |
H21B | 0.60320 | 0.48700 | 0.33030 | 0.0950* | |
H21C | 0.45620 | 0.47980 | 0.39650 | 0.0950* | |
H22A | 0.31540 | 0.45640 | 0.25000 | 0.1070* | |
H22B | 0.46660 | 0.44520 | 0.18000 | 0.1070* | |
H22C | 0.29450 | 0.54070 | 0.14160 | 0.1070* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0862 (5) | 0.0593 (4) | 0.0643 (5) | −0.0131 (4) | 0.0263 (4) | −0.0387 (4) |
N1 | 0.0397 (9) | 0.0192 (7) | 0.0270 (10) | −0.0090 (7) | 0.0051 (7) | −0.0015 (6) |
N2 | 0.0502 (11) | 0.0208 (7) | 0.0285 (10) | −0.0087 (7) | 0.0104 (8) | −0.0048 (7) |
N3 | 0.0299 (8) | 0.0224 (7) | 0.0233 (9) | −0.0067 (6) | 0.0040 (7) | −0.0031 (6) |
N4 | 0.0496 (10) | 0.0220 (7) | 0.0266 (10) | −0.0091 (7) | 0.0105 (8) | −0.0032 (7) |
C2 | 0.0281 (10) | 0.0228 (8) | 0.0303 (11) | −0.0077 (7) | 0.0029 (8) | −0.0035 (7) |
C4 | 0.0300 (10) | 0.0240 (8) | 0.0241 (11) | −0.0102 (7) | 0.0016 (8) | −0.0032 (7) |
C5 | 0.0324 (10) | 0.0249 (9) | 0.0235 (11) | −0.0101 (8) | 0.0015 (8) | −0.0046 (7) |
C6 | 0.0330 (10) | 0.0253 (9) | 0.0265 (11) | −0.0107 (8) | 0.0039 (8) | −0.0031 (7) |
C7 | 0.0497 (13) | 0.0284 (9) | 0.0297 (12) | −0.0155 (9) | 0.0090 (10) | −0.0015 (8) |
C8 | 0.0822 (19) | 0.0650 (16) | 0.0357 (16) | −0.0341 (15) | −0.0157 (13) | 0.0131 (13) |
C9 | 0.0349 (11) | 0.0243 (8) | 0.0249 (11) | −0.0106 (8) | 0.0038 (8) | −0.0017 (7) |
C10 | 0.0374 (12) | 0.0421 (11) | 0.0371 (14) | −0.0129 (9) | 0.0030 (10) | −0.0161 (10) |
C11 | 0.0397 (13) | 0.0511 (13) | 0.0377 (15) | −0.0108 (10) | 0.0100 (10) | −0.0149 (11) |
C12 | 0.0544 (14) | 0.0316 (10) | 0.0298 (13) | −0.0081 (10) | 0.0118 (10) | −0.0106 (9) |
C13 | 0.0580 (15) | 0.0374 (11) | 0.0342 (14) | −0.0190 (11) | −0.0003 (11) | −0.0127 (10) |
C14 | 0.0414 (12) | 0.0386 (11) | 0.0320 (13) | −0.0177 (9) | 0.0016 (9) | −0.0101 (9) |
O1 | 0.0713 (11) | 0.0246 (7) | 0.0401 (10) | −0.0197 (7) | 0.0068 (8) | −0.0060 (6) |
O2 | 0.0928 (14) | 0.0307 (8) | 0.0512 (12) | −0.0215 (9) | 0.0281 (10) | −0.0079 (7) |
O3 | 0.0490 (9) | 0.0442 (8) | 0.0407 (10) | −0.0218 (7) | 0.0068 (7) | −0.0147 (7) |
O4 | 0.0465 (10) | 0.0315 (8) | 0.0734 (14) | −0.0150 (7) | −0.0003 (9) | −0.0181 (8) |
O5 | 0.0688 (12) | 0.0322 (8) | 0.0680 (14) | −0.0223 (8) | −0.0087 (10) | 0.0084 (8) |
O6 | 0.1165 (18) | 0.0539 (11) | 0.0464 (13) | −0.0319 (11) | 0.0168 (12) | −0.0003 (9) |
O7 | 0.211 (3) | 0.0403 (11) | 0.0693 (17) | −0.0356 (15) | 0.0555 (19) | −0.0150 (10) |
N5 | 0.0358 (9) | 0.0314 (9) | 0.0408 (12) | −0.0143 (7) | 0.0063 (8) | −0.0102 (8) |
N6 | 0.0368 (10) | 0.0256 (8) | 0.0675 (16) | −0.0117 (8) | −0.0077 (10) | −0.0056 (9) |
N7 | 0.0626 (13) | 0.0329 (9) | 0.0430 (13) | −0.0222 (9) | 0.0081 (10) | −0.0065 (9) |
C15 | 0.0313 (10) | 0.0242 (9) | 0.0396 (13) | −0.0102 (8) | −0.0005 (9) | −0.0050 (8) |
C16 | 0.0272 (10) | 0.0266 (9) | 0.0389 (13) | −0.0100 (8) | 0.0005 (8) | −0.0060 (8) |
C17 | 0.0235 (10) | 0.0286 (9) | 0.0461 (14) | −0.0078 (8) | 0.0002 (9) | −0.0099 (9) |
C18 | 0.0287 (10) | 0.0213 (9) | 0.0566 (16) | −0.0112 (8) | −0.0009 (9) | −0.0054 (9) |
C19 | 0.0334 (11) | 0.0282 (9) | 0.0449 (14) | −0.0138 (8) | −0.0015 (9) | 0.0012 (9) |
C20 | 0.0343 (11) | 0.0278 (9) | 0.0376 (13) | −0.0114 (8) | 0.0027 (9) | −0.0057 (8) |
S1 | 0.0656 (4) | 0.0337 (3) | 0.0400 (4) | −0.0121 (3) | 0.0110 (3) | −0.0026 (2) |
O8 | 0.0625 (10) | 0.0289 (7) | 0.0378 (10) | −0.0029 (7) | 0.0094 (8) | −0.0074 (6) |
C21 | 0.0658 (18) | 0.0564 (15) | 0.066 (2) | −0.0222 (14) | −0.0113 (15) | −0.0009 (14) |
C22 | 0.077 (2) | 0.0597 (16) | 0.059 (2) | −0.0026 (14) | −0.0029 (15) | −0.0355 (15) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.739 (2) | C9—C14 | 1.376 (3) |
S1—O8 | 1.4997 (19) | C9—C10 | 1.384 (4) |
S1—C21 | 1.781 (3) | C10—C11 | 1.391 (3) |
S1—C22 | 1.773 (3) | C11—C12 | 1.366 (4) |
O1—C15 | 1.238 (2) | C12—C13 | 1.368 (4) |
O2—N5 | 1.217 (2) | C13—C14 | 1.386 (3) |
O3—N5 | 1.229 (2) | C7—H7A | 0.9900 |
O4—N6 | 1.220 (3) | C7—H7B | 0.9900 |
O5—N6 | 1.238 (3) | C8—H8C | 0.9800 |
O6—N7 | 1.194 (3) | C8—H8B | 0.9800 |
O7—N7 | 1.208 (3) | C8—H8A | 0.9800 |
N1—C6 | 1.377 (3) | C10—H10 | 0.9500 |
N1—C2 | 1.360 (3) | C11—H11 | 0.9500 |
N2—C2 | 1.322 (3) | C13—H13 | 0.9500 |
N3—C2 | 1.334 (2) | C14—H14 | 0.9500 |
N3—C4 | 1.344 (2) | C15—C16 | 1.464 (3) |
N4—C4 | 1.326 (2) | C15—C20 | 1.452 (3) |
N1—H1 | 0.8800 | C16—C17 | 1.376 (3) |
N2—H2B | 0.8800 | C17—C18 | 1.380 (3) |
N2—H2A | 0.8800 | C18—C19 | 1.373 (3) |
N4—H4A | 0.8800 | C19—C20 | 1.376 (3) |
N4—H4B | 0.8800 | C17—H17 | 0.9500 |
N5—C16 | 1.452 (3) | C19—H19 | 0.9500 |
N6—C18 | 1.458 (3) | C21—H21A | 0.9800 |
N7—C20 | 1.455 (3) | C21—H21B | 0.9800 |
C4—C5 | 1.433 (3) | C21—H21C | 0.9800 |
C5—C6 | 1.367 (3) | C22—H22A | 0.9800 |
C5—C9 | 1.489 (3) | C22—H22B | 0.9800 |
C6—C7 | 1.495 (3) | C22—H22C | 0.9800 |
C7—C8 | 1.526 (5) | | |
| | | |
Cl1···C22i | 3.496 (4) | C4···C17v | 3.542 (3) |
Cl1···H22Bi | 2.9000 | C4···N6ix | 3.362 (3) |
S1···C13ii | 3.573 (2) | C4···O5ix | 3.299 (3) |
S1···C12ii | 3.557 (2) | C5···O3v | 3.157 (3) |
S1···H4Bii | 3.0100 | C6···O3v | 3.241 (3) |
O1···O7 | 2.621 (3) | C7···O7 | 3.138 (3) |
O1···N1 | 2.827 (2) | C8···O7 | 3.264 (4) |
O1···C2 | 3.269 (2) | C11···C11x | 3.373 (4) |
O1···N7 | 2.875 (3) | C12···S1ii | 3.557 (2) |
O1···O2 | 2.656 (3) | C13···S1ii | 3.573 (2) |
O1···C21iii | 3.417 (4) | C14···N4 | 3.338 (3) |
O1···N2 | 2.827 (2) | C16···C2v | 3.464 (3) |
O1···N5 | 2.917 (2) | C16···N3v | 3.366 (3) |
O2···O1 | 2.656 (3) | C17···C4v | 3.542 (3) |
O2···N2 | 2.862 (2) | C17···C17iv | 3.509 (3) |
O2···O4iv | 3.167 (3) | C17···N3v | 3.268 (3) |
O3···C4v | 3.255 (3) | C18···O3iv | 3.235 (3) |
O3···C18iv | 3.235 (3) | C21···O1iii | 3.417 (4) |
O3···N6iv | 3.017 (3) | C22···Cl1xi | 3.496 (4) |
O3···C2v | 3.402 (3) | C2···H4Aii | 3.0800 |
O3···C6v | 3.241 (3) | C4···H4Aii | 2.9900 |
O3···O4iv | 2.977 (3) | C8···H1 | 2.9800 |
O3···C5v | 3.157 (3) | C9···H7B | 2.6000 |
O4···O2iv | 3.167 (3) | C9···H4B | 2.5000 |
O4···O3iv | 2.977 (3) | C10···H7B | 2.9800 |
O4···N3vi | 3.164 (3) | C11···H11x | 3.0300 |
O4···C2vi | 3.417 (3) | C14···H4B | 2.7900 |
O4···N5iv | 2.964 (3) | C15···H2B | 3.0700 |
O5···C4vi | 3.299 (3) | C17···H17iv | 3.0400 |
O7···C7 | 3.138 (3) | C19···H14vi | 3.0900 |
O7···C8 | 3.264 (4) | H1···O1 | 2.0500 |
O7···O1 | 2.621 (3) | H1···H7A | 2.4600 |
O8···N2 | 2.953 (3) | H1···C8 | 2.9800 |
O8···N4ii | 2.765 (2) | H1···H8A | 2.5300 |
O1···H1 | 2.0500 | H1···O7 | 2.6900 |
O1···H2B | 2.0400 | H1···H2B | 2.2700 |
O2···H2B | 2.1800 | H2A···O8 | 2.0800 |
O2···H21C | 2.6000 | H2B···O1 | 2.0400 |
O2···H22A | 2.6900 | H2B···C15 | 3.0700 |
O3···H17 | 2.3000 | H2B···H1 | 2.2700 |
O3···H10v | 2.7200 | H2B···O2 | 2.1800 |
O4···H21Civ | 2.8100 | H4A···C2ii | 3.0800 |
O4···H17 | 2.4100 | H4A···O8ii | 2.9100 |
O5···H22Biv | 2.8200 | H4A···N3ii | 2.1200 |
O5···H19 | 2.4200 | H4A···C4ii | 2.9900 |
O6···H11vii | 2.7400 | H4A···H4Aii | 2.4500 |
O6···H14vi | 2.8700 | H4B···S1ii | 3.0100 |
O6···H7Bviii | 2.8100 | H4B···C9 | 2.5000 |
O6···H19 | 2.3600 | H4B···C14 | 2.7900 |
O7···H7A | 2.3800 | H4B···O8ii | 2.0500 |
O7···H8A | 2.7700 | H7A···H1 | 2.4600 |
O7···H1 | 2.6900 | H7A···H8Bviii | 2.5700 |
O8···H2A | 2.0800 | H7A···O7 | 2.3800 |
O8···H4Bii | 2.0500 | H7B···C10 | 2.9800 |
O8···H4Aii | 2.9100 | H7B···O6viii | 2.8100 |
N1···O1 | 2.827 (2) | H7B···C9 | 2.6000 |
N2···O8 | 2.953 (3) | H8A···H1 | 2.5300 |
N2···O1 | 2.827 (2) | H8A···N1 | 2.8500 |
N2···O2 | 2.862 (2) | H8A···O7 | 2.7700 |
N3···N4ii | 2.996 (2) | H8B···H7Aviii | 2.5700 |
N3···O4ix | 3.164 (3) | H8C···H13xii | 2.5700 |
N3···N6ix | 3.159 (3) | H10···O3v | 2.7200 |
N3···C16v | 3.366 (3) | H11···C11x | 3.0300 |
N3···C17v | 3.268 (3) | H11···O6xiii | 2.7400 |
N4···N3ii | 2.996 (2) | H13···H8Cxii | 2.5700 |
N4···O8ii | 2.765 (2) | H14···H19ix | 2.4300 |
N4···C14 | 3.338 (3) | H14···O6ix | 2.8700 |
N5···C2v | 3.208 (3) | H14···C19ix | 3.0900 |
N5···O4iv | 2.964 (3) | H17···C17iv | 3.0400 |
N5···O1 | 2.917 (2) | H17···O4 | 2.4100 |
N6···C4vi | 3.362 (3) | H17···O3 | 2.3000 |
N6···O3iv | 3.017 (3) | H19···O5 | 2.4200 |
N6···N3vi | 3.159 (3) | H19···O6 | 2.3600 |
N7···O1 | 2.875 (3) | H19···H14vi | 2.4300 |
N1···H8A | 2.8500 | H21C···O2 | 2.6000 |
N3···H4Aii | 2.1200 | H21C···H22A | 2.5000 |
C2···O1 | 3.269 (2) | H21C···O4iv | 2.8100 |
C2···O4ix | 3.417 (3) | H22A···O2 | 2.6900 |
C2···N5v | 3.208 (3) | H22A···H21C | 2.5000 |
C2···C16v | 3.464 (3) | H22B···Cl1xi | 2.9000 |
C2···O3v | 3.402 (3) | H22B···O5iv | 2.8200 |
C4···O3v | 3.255 (3) | | |
| | | |
C21—S1—C22 | 97.39 (16) | C8—C7—H7A | 109.00 |
O8—S1—C21 | 105.84 (13) | C6—C7—H7A | 109.00 |
O8—S1—C22 | 105.76 (15) | H7A—C7—H7B | 108.00 |
C2—N1—C6 | 121.51 (15) | C7—C8—H8B | 109.00 |
C2—N3—C4 | 117.92 (17) | H8B—C8—H8C | 109.00 |
C6—N1—H1 | 119.00 | C7—C8—H8A | 110.00 |
C2—N1—H1 | 119.00 | H8A—C8—H8B | 109.00 |
C2—N2—H2A | 120.00 | H8A—C8—H8C | 109.00 |
C2—N2—H2B | 120.00 | C7—C8—H8C | 109.00 |
H2A—N2—H2B | 120.00 | C11—C10—H10 | 120.00 |
C4—N4—H4A | 120.00 | C9—C10—H10 | 120.00 |
H4A—N4—H4B | 120.00 | C12—C11—H11 | 120.00 |
C4—N4—H4B | 120.00 | C10—C11—H11 | 120.00 |
O2—N5—O3 | 121.25 (19) | C14—C13—H13 | 120.00 |
O2—N5—C16 | 120.36 (18) | C12—C13—H13 | 120.00 |
O3—N5—C16 | 118.39 (16) | C13—C14—H14 | 119.00 |
O4—N6—O5 | 124.15 (18) | C9—C14—H14 | 119.00 |
O5—N6—C18 | 117.1 (2) | O1—C15—C16 | 124.6 (2) |
O4—N6—C18 | 118.7 (2) | O1—C15—C20 | 123.8 (2) |
O6—N7—C20 | 120.10 (18) | C16—C15—C20 | 111.65 (16) |
O7—N7—C20 | 119.0 (2) | C15—C16—C17 | 123.7 (2) |
O6—N7—O7 | 120.6 (2) | N5—C16—C15 | 120.63 (16) |
N1—C2—N2 | 118.34 (16) | N5—C16—C17 | 115.61 (19) |
N2—C2—N3 | 119.92 (18) | C16—C17—C18 | 119.6 (2) |
N1—C2—N3 | 121.75 (17) | N6—C18—C17 | 118.6 (2) |
N3—C4—N4 | 116.45 (18) | N6—C18—C19 | 120.0 (2) |
N4—C4—C5 | 120.62 (17) | C17—C18—C19 | 121.24 (18) |
N3—C4—C5 | 122.93 (16) | C18—C19—C20 | 119.7 (2) |
C4—C5—C6 | 116.83 (17) | C15—C20—C19 | 124.1 (2) |
C6—C5—C9 | 123.21 (18) | N7—C20—C15 | 119.84 (17) |
C4—C5—C9 | 119.91 (16) | N7—C20—C19 | 116.05 (19) |
N1—C6—C5 | 118.88 (18) | C16—C17—H17 | 120.00 |
N1—C6—C7 | 116.49 (16) | C18—C17—H17 | 120.00 |
C5—C6—C7 | 124.56 (18) | C18—C19—H19 | 120.00 |
C6—C7—C8 | 110.9 (2) | C20—C19—H19 | 120.00 |
C10—C9—C14 | 118.6 (2) | S1—C21—H21A | 109.00 |
C5—C9—C14 | 122.01 (19) | S1—C21—H21B | 109.00 |
C5—C9—C10 | 119.26 (18) | S1—C21—H21C | 110.00 |
C9—C10—C11 | 120.6 (2) | H21A—C21—H21B | 109.00 |
C10—C11—C12 | 119.2 (3) | H21A—C21—H21C | 110.00 |
Cl1—C12—C11 | 119.0 (2) | H21B—C21—H21C | 109.00 |
C11—C12—C13 | 121.3 (2) | S1—C22—H22A | 110.00 |
Cl1—C12—C13 | 119.70 (19) | S1—C22—H22B | 109.00 |
C12—C13—C14 | 119.1 (2) | S1—C22—H22C | 109.00 |
C9—C14—C13 | 121.2 (3) | H22A—C22—H22B | 109.00 |
C8—C7—H7B | 109.00 | H22A—C22—H22C | 109.00 |
C6—C7—H7B | 109.00 | H22B—C22—H22C | 109.00 |
| | | |
C6—N1—C2—N2 | −175.86 (19) | C6—C5—C9—C10 | −81.3 (3) |
C6—N1—C2—N3 | 3.8 (3) | C6—C5—C9—C14 | 102.8 (2) |
C2—N1—C6—C5 | 0.0 (3) | C5—C6—C7—C8 | −105.3 (2) |
C2—N1—C6—C7 | −177.1 (2) | N1—C6—C7—C8 | 71.6 (3) |
C4—N3—C2—N1 | −4.0 (3) | C5—C9—C10—C11 | −177.27 (19) |
C4—N3—C2—N2 | 175.69 (19) | C14—C9—C10—C11 | −1.2 (3) |
C2—N3—C4—N4 | −178.82 (19) | C5—C9—C14—C13 | 176.23 (19) |
C2—N3—C4—C5 | 0.5 (3) | C10—C9—C14—C13 | 0.3 (3) |
O2—N5—C16—C17 | 179.3 (2) | C9—C10—C11—C12 | 2.0 (3) |
O3—N5—C16—C15 | −177.14 (19) | C10—C11—C12—C13 | −1.8 (3) |
O2—N5—C16—C15 | 2.6 (3) | C10—C11—C12—Cl1 | 178.19 (18) |
O3—N5—C16—C17 | −0.4 (3) | C11—C12—C13—C14 | 0.9 (3) |
O5—N6—C18—C19 | −0.6 (3) | Cl1—C12—C13—C14 | −179.10 (17) |
O5—N6—C18—C17 | −177.5 (2) | C12—C13—C14—C9 | −0.1 (3) |
O4—N6—C18—C17 | 1.5 (3) | O1—C15—C16—N5 | −5.2 (3) |
O4—N6—C18—C19 | 178.4 (2) | O1—C15—C16—C17 | 178.4 (2) |
O6—N7—C20—C15 | −170.8 (2) | C20—C15—C16—N5 | 176.53 (18) |
O6—N7—C20—C19 | 10.9 (3) | C20—C15—C16—C17 | 0.1 (3) |
O7—N7—C20—C15 | 15.2 (4) | O1—C15—C20—N7 | 5.4 (3) |
O7—N7—C20—C19 | −163.2 (3) | O1—C15—C20—C19 | −176.4 (2) |
N4—C4—C5—C9 | 5.2 (3) | C16—C15—C20—N7 | −176.31 (18) |
N3—C4—C5—C6 | 3.0 (3) | C16—C15—C20—C19 | 1.9 (3) |
N3—C4—C5—C9 | −174.16 (19) | N5—C16—C17—C18 | −178.48 (19) |
N4—C4—C5—C6 | −177.6 (2) | C15—C16—C17—C18 | −1.9 (3) |
C9—C5—C6—N1 | 173.90 (19) | C16—C17—C18—N6 | 178.69 (19) |
C9—C5—C6—C7 | −9.3 (3) | C16—C17—C18—C19 | 1.8 (3) |
C4—C5—C9—C10 | 95.7 (2) | N6—C18—C19—C20 | −176.72 (19) |
C4—C5—C6—C7 | 173.6 (2) | C17—C18—C19—C20 | 0.1 (3) |
C4—C5—C6—N1 | −3.2 (3) | C18—C19—C20—N7 | 176.19 (19) |
C4—C5—C9—C14 | −80.2 (3) | C18—C19—C20—C15 | −2.1 (3) |
Symmetry codes: (i) x−1, y+1, z+1; (ii) −x, −y+2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y+1, −z+1; (vi) x, y−1, z; (vii) x+1, y−1, z; (viii) −x, −y+1, −z+2; (ix) x, y+1, z; (x) −x−1, −y+2, −z+2; (xi) x+1, y−1, z−1; (xii) −x, −y+2, −z+2; (xiii) x−1, y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.88 | 2.05 | 2.827 (2) | 147 |
N2—H2A···O8 | 0.88 | 2.08 | 2.953 (3) | 169 |
N2—H2B···O1 | 0.88 | 2.04 | 2.827 (2) | 148 |
N2—H2B···O2 | 0.88 | 2.18 | 2.862 (2) | 134 |
N4—H4A···N3ii | 0.88 | 2.12 | 2.996 (2) | 170 |
N4—H4B···O8ii | 0.88 | 2.05 | 2.765 (2) | 137 |
C7—H7A···O7 | 0.99 | 2.38 | 3.138 (3) | 133 |
C17—H17···O3 | 0.95 | 2.30 | 2.636 (3) | 100 |
Symmetry code: (ii) −x, −y+2, −z+1. |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | C6H10N3O2+·C6H2N3O7− | C12H14ClN4+·C6H2N3O7−·C2H6OS |
Mr | 384.28 | 555.97 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 120 | 200 |
a, b, c (Å) | 8.8796 (2), 13.2847 (3), 14.1395 (3) | 9.3365 (3), 11.1245 (3), 13.1861 (6) |
α, β, γ (°) | 99.820 (1), 100.701 (1), 105.095 (1) | 83.779 (3), 86.057 (3), 65.784 (3) |
V (Å3) | 1539.68 (6) | 1241.24 (8) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.14 | 0.30 |
Crystal size (mm) | 0.16 × 0.12 × 0.06 | 0.47 × 0.26 × 0.21 |
|
Data collection |
Diffractometer | Bruker–Nonius KappaCCD diffractometer | Oxford Diffraction Gemini diffractometer |
Absorption correction | – | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | – | 0.873, 0.940 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27465, 7048, 5725 | 17314, 7722, 3648 |
Rint | 0.039 | 0.029 |
(sin θ/λ)max (Å−1) | 0.651 | 0.757 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.121, 1.06 | 0.054, 0.172, 0.93 |
No. of reflections | 7048 | 7722 |
No. of parameters | 487 | 337 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −0.40 | 1.09, −0.60 |
Selected geometric parameters (Å, º) for (I) topO3A—C9A | 1.251 (2) | O7B—N5B | 1.227 (2) |
O4A—N4A | 1.221 (2) | O8B—N6B | 1.233 (2) |
O5A—N4A | 1.233 (2) | O9B—N6B | 1.226 (2) |
O6A—N5A | 1.229 (3) | N1A—C2A | 1.362 (3) |
O7A—N5A | 1.234 (2) | N1A—C6A | 1.367 (2) |
O8A—N6A | 1.221 (2) | N3A—C4A | 1.329 (3) |
O9A—N6A | 1.230 (2) | N3A—C2A | 1.336 (3) |
O3B—C9B | 1.251 (2) | N1B—C6B | 1.365 (3) |
O4B—N4B | 1.229 (3) | N1B—C2B | 1.366 (3) |
O5B—N4B | 1.224 (3) | N3B—C2B | 1.335 (3) |
O6B—N5B | 1.229 (3) | N3B—C4B | 1.328 (3) |
| | | |
C2A—N1A—C6A | 120.27 (16) | C2B—N1B—C6B | 120.44 (16) |
C2A—N3A—C4A | 116.36 (17) | C2B—N3B—C4B | 116.42 (18) |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A1···O5B | 0.8600 | 2.2100 | 3.047 (3) | 165.00 |
N1A—H1A···O3A | 0.8600 | 1.9700 | 2.720 (2) | 145.00 |
N1A—H1A···O4A | 0.8600 | 2.5100 | 3.226 (2) | 142.00 |
N1B—H1B···O3B | 0.8600 | 1.9300 | 2.707 (2) | 149.00 |
N2A—H2A2···O3A | 0.8600 | 2.0300 | 2.771 (2) | 143.00 |
N2A—H2A2···O9A | 0.8600 | 2.2700 | 2.970 (2) | 138.00 |
N2B—H2B1···O5Ai | 0.8600 | 2.2400 | 3.017 (2) | 151.00 |
N2B—H2B2···O3B | 0.8600 | 2.1100 | 2.842 (2) | 142.00 |
N2B—H2B2···O9B | 0.8600 | 2.4000 | 3.134 (2) | 144.00 |
C7A—H7A2···O6B | 0.9600 | 2.4800 | 3.050 (3) | 118.00 |
C5A—H5A···O7Aii | 0.9300 | 2.2900 | 3.100 (2) | 146.00 |
C5B—H5B···O7Biii | 0.9300 | 2.3100 | 3.142 (2) | 148.00 |
C13B—H13B···O8B | 0.9300 | 2.3200 | 2.643 (3) | 100.00 |
C7B—H7B3···O4Aiv | 0.9600 | 2.4700 | 3.346 (3) | 152.00 |
Symmetry codes: (i) x+1, y−1, z; (ii) x, y, z−1; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+2. |
Selected geometric parameters (Å, º) for (II) topCl1—C12 | 1.739 (2) | O5—N6 | 1.238 (3) |
S1—O8 | 1.4997 (19) | O6—N7 | 1.194 (3) |
S1—C21 | 1.781 (3) | O7—N7 | 1.208 (3) |
S1—C22 | 1.773 (3) | N1—C6 | 1.377 (3) |
O1—C15 | 1.238 (2) | N1—C2 | 1.360 (3) |
O2—N5 | 1.217 (2) | N3—C2 | 1.334 (2) |
O3—N5 | 1.229 (2) | N3—C4 | 1.344 (2) |
O4—N6 | 1.220 (3) | | |
| | | |
C21—S1—C22 | 97.39 (16) | C2—N1—C6 | 121.51 (15) |
O8—S1—C21 | 105.84 (13) | C2—N3—C4 | 117.92 (17) |
O8—S1—C22 | 105.76 (15) | | |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.8800 | 2.0500 | 2.827 (2) | 147.00 |
N2—H2A···O8 | 0.8800 | 2.0800 | 2.953 (3) | 169.00 |
N2—H2B···O1 | 0.8800 | 2.0400 | 2.827 (2) | 148.00 |
N2—H2B···O2 | 0.8800 | 2.1800 | 2.862 (2) | 134.00 |
N4—H4A···N3i | 0.8800 | 2.1200 | 2.996 (2) | 170.00 |
N4—H4B···O8i | 0.8800 | 2.0500 | 2.765 (2) | 137.00 |
Symmetry code: (i) −x, −y+2, −z+1. |
Picric acid functions not only as an acceptor to form π-stacking complexes with aromatic biomolecules but also as an acidic ligand to form salts with polar biomolecules through specific electrostatic or hydrogen-bonding interactions (In et al., 1997). Picric acid forms charge-transfer complexes with organic compounds. Crystalline picrates have commonly been used in the preparation of amine derivatives in qualitative organic chemistry (Shriner et al., 1980). Dimethyl sulfoxide (DMSO) is a versatile solvent, which can dissolve various organic substances, and can form crystalline solvates in which it is either disordered (Deetz et al., 2000; Harper et al., 2001) or well ordered (TranQui et al., 1998). Hydrogen bonding plays a key role in molecular recognition and crystal engineering research (Desiraju, 1989). Some derivatives of pyrimidines are used as antiviral, antitumor and cardiovascular agents (Atwal et al., 1989). Pyrimethamine is a well known antifolate drug used in the treatment of malaria. In the chemotheraphy of malaria and neoplastic diseases, substituted 2,4-diaminopyrimidines are widely employed as metabolic inhibitors of pathways leading to the synthesis of proteins and nucleic acid (Hitchings & Burchall, 1965). Pyrimethamine is also used along with other drugs for the treatment of opportunistic infections in patients suffering with AIDS (Tanaka et al., 2004). The crystal structures of pyrimethamine (Sethuraman & Thomas Muthiah, 2002) and 2-amino-4,6-dimethoxy pyrimidine have also been reported (Low et al., 2002). Hydrogen-bonding patterns in aminopyrimidine–carboxylate salts have been recently reviewed (Schwalbe & Cody, 2006). The crystal structures of 2-amino-4,6-dimethoxypyrimidinium 4-hydroxybenzoate monohydrate (Thanigaimani et al., 2007a) and 2-amino-4,6-dimethoxypyrimidinium salicylate (Thanigaimani et al., 2007b) have been reported by us. The present study was undertaken to obtain more information regarding patterns of hydrogen bonds in these types of compounds.
ORTEPII (Johnson, 1976) views of the title compounds, (I) and (II), are shown in Figs. 1 and 2, and selected geometric parameters are given in Tables 1 and 3. In (I), the asymmetric unit contains pairs of 2-amino-4,6-dimethoxypyrimidinium cations (A and B) and picrate anions (A and B). In (II), the asymmetric unit contains one protonated pyrimethaminium (PMN) cation, one picrate anion and one molecule of dimethyl sulfoxide (DMSO) solvate. In the two compounds, the pyrimidine rings are protonated at atom N1. Protonation of the pyrimidine base on the N1 site is reflected by an increase in bond angle at N1 [the C2—N1—C6 angle is 120.27 (16)° in cation A of (I), 120.44 (16)° in cation B of (I) and 121.51 (15)° in (II)] when compared with that at the unprotonated atom N3 [the C2—N3—C4 angle is 116.36 (17)° in cation A of (I), 116.42 (18)° in cation B of (I) and 117.92 (17)° in (II)]. The key conformational features of the PMN cations are described by two angles. The first is the dihedral angle between the 2,4-diaminopyrimidine and the 4-chlorophenyl mean planes. The second is the torsion angle that represents the deviation of the ethyl group from the pyrimidine plane. The dihedral angle between the pyrimidine and benzene ring is 81.05 (10)° and the C5—C6—C7—C8 torsion angle is -105.3 (2)°. These values are close to those observed in modeling studies of dihydrofolate reductase–pyrimethamine complexes, which indicates that these angles play an important role in the effective docking of the drug molecule in the active site of the enzyme (Sansom et al., 1989).
For ions A of (I), the phenolate O atom and two of the nitro O atoms (O9A and O4A) of the picrate anion form bifurcated N—H···O hydrogen bonds with the protonated pyrimidine and amine N atoms of the 2-amino-4,6-dimethoxypyrimidinium cation, forming three rings with graph-set notations R12(6), R21(6) and R12(6) (Etter, 1990; Bernstein et al., 1995). A similar type of interaction has been observed in the crystal structure of 2-aminopyrimidinium picrate (Narayana et al., 2008). However, in cation B and compound (II), the protonated N atoms (N1B and N1) do not form bifurcated hydrogen bonds with the nitro group (N4B and N7) of the picrate anion, resulting in only two rings with graph-set notations R21(6) and R12(6). This type of interaction has also been reported in the crystal structure of 2-amino-4,6-dimethylpyrimidinium picrate (Subashini et al., 2006). Ions A and B form individual chains via C—H···O hydrogen bonds. These two chains are interlinked by N—H···O hydrogen bonds to form a supramolecular sheet with graph-set notation R66(32) (Fig. 3).
In (II), the two inversion-related PMN cations are linked through a pair of N—H···N hydrogen bonds involving the 4-amino group and atom N3 of the pyrimidine ring, generating an R22(8) ring motif. No similar interactions are observed in (I). In addition to the pairing, the O atom from the DMSO solvent molecule bridges the 2-amino and 4-amino groups on either side of the paired bases, resulting in a self-complementary DADA (D represents a hydrogen-bond donor and A a hydrogen-bond acceptor) array of quadruple hydrogen-bonding patterns. The corresponding graph-set notations are R32(8), R22(8) and R32(8) (Fig. 4). This type of DADA array of quadruple hydrogen bonds has been observed in PMN carboxylates (Stanley et al., 2005).
In (I), π–π stacking interactions between the aromatic rings are also observed. The pyrimidine ring of 2-amino-4,6-dimethoxypyrimidinium (cation A) forms stacking interactions with the aryl rings of the picrate anion (A), with interplanar and centroid–centroid distances of 3.2953 (7) and 3.8433 (11) Å, respectively, and a slip angle (the angle between the centroid vector and the normal to the plane) of 30.97°. A similar type of stacking is also observed between the 2-amino-4,6-dimethoxypyrimidinium cation B, which forms stacking interactions with the aryl rings of the picrate anion A, with interplanar and centroid–centroid distances of 3.3652 (8) and 3.8659 (11) Å, respectively, the slip angle being 29.49°. These are typical aromatic stacking values (Hunter, 1994).