4-Di­methyl­amino­pyridinium picrate: supramolecular aggregation through extensive N—H⋯O and C—H⋯O interactions

Vembu, N.; Nallu, M.; Garrison, J.; Youngs, W.J.

doi:10.1107/S1600536803012212

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4-Dimethylaminopyridinium picrate: supramolecular aggregation through extensive N—HO and C—HO interactions

N. Vembu, M. Nallu, J. Garrison and W. J. Youngs

The crystal structure of the title compound, C₆H₂N₃O₇·C₇H₁₁N₂, contains two 4-dimethylaminopyridinium cations and two picrate anions in the asymmetric unit. The N—H

O and C—H

O interactions generate rings of graph set motifs S(5), R²₁(6), R¹₂(5), R²₁(4), R¹₂(7), R¹₂(6), R²₂(8), R²₂(10) and R²₂(14), which contribute to the supramolecular aggregation through bifurcated and trifurcated bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012212/ci6222sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803012212/ci6222Isup2.hkl Contains datablock I

CCDC reference: 217437

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.072
wR factor = 0.155
Data-to-parameter ratio = 12.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

The design of organic polar crystals for quadratic non-linear optical applications is supported by the observation that the organic molecules containing π-electron systems asymmetrized by electron donor and acceptor groups are highly polarizable entities in which problems of transparency and crystal growth may arise from their molecular crystal packing (Pecaut & Bagieu-Beucher, 1993). It is known that picric acid acts not only as an acceptor to form various π-stacking complexes with other aromatic molecules, but also as an acidic ligand to form salts through specific electrostatic or hydrogen-bonding interactions (In et al., 1997). The bonding of electron-donor acceptor picric acid complexes strongly depends on the nature of the partners. The linkage could involve not only electrostatic interactions, but also the formation of molecular complexes (Zadrenko et al., 1997). It has been reported that proton transferred thermochromic complexes were formed between phenols and amines in apolar solvents at low temperature if an appropriate hydrogen bonding network between phenols and amines can stabilize it (Mizutani et al., 1998). Pyridinium picrate has been reported in two crystalline phases and it appear in both phases as an internally linked hydrogen-bonded ion pair and both phases are termed as molecular crystals rather than salts based on their structural arrangements (Botoshansky et al., 1994). It was reported that the reaction of 4-nitrophenol with 4-dimethylaminopyridine resulted in the formation of a new NLO material which was found to be an association of three components, 4-nitrophenolate/4-nitrophenol/4-dimethylaminopyridinium (Evans et al., 1998). The X-ray structure determination of the title compound, (I), was undertaken to study the nature of interaction between 4-dimethylaminopyridine and picric acid in the solid state. This study may serve as a forerunner for assessing the optical property of the title compound.

The asymmetric unit of (I) contains two 4-dimethylaminopyridinium cations and two picrate anions (Fig.1). The bond lengths and angles of the picrate and dimethylaminopyridinium moieties (Table 1) are comparable to those found in related structures reported in the Cambridge Structural Database (Allen, 2002; Bruno et al., 2002). The crystal structure of (I) is stabilized by N—H···O and C—H···O interactions. The range of H···O distances (Table 2) found in (I) agrees with those found for N—H···O (Jeffrey, 1997) and C—H···O bonds (Desiraju & Steiner, 1999).

The C3—H3···O3 and C3—H3···O4 interactions constitute a pair of bifurcated donor bonds generating two fused rings each of graph set (Etter, 1990; Bernstein et al., 1995) motif, S(5). A similar motif is generated by the C5—H5···O5 and C5—H5···O6 interactions. The C9—H9···O10 and C9—H9···O11 interactions form a pair of bifurcated donor bonds generating two fused rings each of graph set motif, S(5). Similar motif is generated by the C11—H11···O12 and C11—H11···O13 interactions. The N7—H'···O1 and N7—H'···O2 interactions constitute a pair of bifurcated donor bonds generating a ring of graph set motif R²₁(6). The N7—H'···O1 and C13—H13···O1 interactions form a pair of bifurcated acceptor bonds generating a ring of graph set motif R¹₂(5). The N7—H'···O2 and C17—H17···O2 interactions form a pair of bifurcated acceptor bonds generating a ring of graph set motif R¹₂(5). The N9—H"···O8 and N9—H"···O14 interactions constitute a pair of bifurcated donor bonds generating a ring of graph set motif R²₁(6). The N9—H"···O8 and C20—H20···O8 interactions form a pair of bifurcated acceptor bonds generating a ring of graph set motif R¹₂(5). The N9—H"···O14 and C24—H24···O14 interactions form a pair of bifurcated acceptor bonds generating a ring of graph set motif R¹₂(5). The C5—H5···O10 interaction links the two anions present in the asymmetric unit.

The C11—H11···O4ⁱ and C11—H11···O12ⁱ interactions constitute a pair of bifurcated donor bonds involving acceptor O atoms from symmetry related anions. The C9—H9···O2ⁱⁱ and C9—H9···O3ⁱⁱ interactions constitute a pair of bifurcated donor bonds and they generate a ring of graph set motif R²₁(4). The C21—H21···O6ⁱⁱⁱ and C25—H25C···O6ⁱⁱⁱ interactions form a pair of bifurcated acceptor bonds generating a ring of graph set motif R¹₂(7). The C16—H16···O5^iv and C17—H17···O5^iv interactions constitute a pair of bifurcated acceptor bonds generating a ring of graph set motif R¹₂(5). The above motif can best be regarded as a three center symmetrical hydrogen-bonded chelate (Desiraju, 1989; Vembu et al., 2003b; Vembu et al., 2003c; Vembu, Nallu, Garrison, Hindi & Youngs, 2003). The C17—H17···O11^iv and C17—H17···O5^iv interactions constitute a pair of bifurcated donor bonds. The C17—H17···O11^iv and C23—H23···O11^iv interactions form a pair of bifurcated acceptor bonds. The C19—H19B.·O13^v and C16—H16···O13^v interactions form a pair of bifurcated acceptor bonds generating a ring of graph set R¹₂(7).

The C26—H26C···O13^v and C26—H26C···O14^v interactions constitute a pair of bifurcated donor bonds generating a ring of graph set motif R²₁(4). The C19—H19B···O13^v, C16—H16···O13^v and C26—H26C···O13^v interactions can be collectively termed as trifurcated acceptor bonds. The C19—H19A···O7^vi and C18—H18A···O7^vi interactions form a pair of bifurcated acceptor bonds generating a ring of graph set R¹₂(6). The C25—H25A···O9^vi and C26—H26B···O9^vi interactions constitute a pair of bifurcated acceptor bonds generating a ring of graph set R¹₂(6). The C25—H25B···O12^viii and C26—H26A···O11^viii interactions generate a fork motif (Vembu et al., 2003a) of graph set R²₂(8). The C26—H26A···O11^viii and C24—H24···O9^viii interactions generate a ring of graph set R²₂(14). Another R²₂(14) motif is formed by the C25—H25B···O12^viii and C24—H24···O9^viii interactions. The C25—H25A···O3^ix and C25—H25B···O4^ix interactions generate a ring of graph set R²₂(10). The symmetry codes are given in Table 2.

The three dimensional arrangement of the picrate and the dimethylaminopyridinium ions in the unit cell shows that the title molecule is an internally linked hydrogen-bonded ion pair and hence can be termed as a molecular crystal rather than a salt.

Experimental top

Picric acid (5.2 mmol) dissolved in dichloromethane (25 ml) was added dropwise to 4-dimethylaminopyridine (5.7 mmol) in dichloromethane (25 ml). The above solution was constantly stirred at room temperature for 2 h. The precipitated product was filtered off and recrystallized from aqueous ethanol.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The contents of the asymmetric unit of (I), showing 50% probability displacement ellipsoids and, N—H···O and C—H···O interactions.
	Fig. 2. A view of the molecular packing of (I).

4-N,N-Dimethylaminopyridinium 2,4,6-trinitrophenolate top

Crystal data top

C₇H₁₁N₂·C₆H₂N₃O₇	F(000) = 1456
M_r = 351.28	D_x = 1.597 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 197–199 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.274 (4) Å	Cell parameters from 5444 reflections
b = 12.617 (3) Å	θ = 2.4–28.2°
c = 19.795 (4) Å	µ = 0.13 mm⁻¹
β = 129.996 (13)°	T = 100 K
V = 2922.4 (12) Å³	Block, yellow
Z = 8	0.50 × 0.40 × 0.20 mm

Data collection top

CCD area detector diffractometer	6947 independent reflections
Radiation source: fine-focus sealed tube	5744 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→19
T_min = 0.937, T_max = 0.974	k = −16→16
24887 measured reflections	l = −26→26

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	All H-atom parameters refined
S = 1.20	w = 1/[σ²(F_o²) + (0.0449P)² + 2.9161P] where P = (F_o² + 2F_c²)/3
6947 reflections	(Δ/σ)_max < 0.001
555 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₇H₁₁N₂·C₆H₂N₃O₇	V = 2922.4 (12) Å³
M_r = 351.28	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.274 (4) Å	µ = 0.13 mm⁻¹
b = 12.617 (3) Å	T = 100 K
c = 19.795 (4) Å	0.50 × 0.40 × 0.20 mm
β = 129.996 (13)°

Data collection top

CCD area detector diffractometer	6947 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5744 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.974	R_int = 0.069
24887 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.155	All H-atom parameters refined
S = 1.20	Δρ_max = 0.50 e Å⁻³
6947 reflections	Δρ_min = −0.32 e Å⁻³
555 parameters

Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.39985 (15)	0.58218 (14)	0.08462 (11)	0.0210 (4)
O2	0.23796 (16)	0.64307 (14)	−0.08376 (11)	0.0224 (4)
O3	0.20307 (19)	0.81007 (15)	−0.10400 (12)	0.0322 (5)
O4	0.23307 (16)	1.02045 (15)	0.10762 (12)	0.0272 (4)
O5	0.32326 (16)	0.96172 (15)	0.24010 (12)	0.0267 (4)
O6	0.54812 (17)	0.64622 (18)	0.33229 (12)	0.0368 (5)
O7	0.46009 (16)	0.51830 (14)	0.23918 (12)	0.0260 (4)
O8	0.14841 (15)	0.58289 (13)	0.09176 (11)	0.0195 (4)
O9	0.20398 (16)	0.54601 (14)	0.25612 (12)	0.0241 (4)
O10	0.33094 (15)	0.66845 (16)	0.32372 (11)	0.0284 (4)
O11	0.07247 (16)	0.99157 (14)	0.22318 (11)	0.0236 (4)
O12	−0.02541 (16)	1.03188 (14)	0.08560 (11)	0.0219 (4)
O13	−0.10633 (14)	0.76201 (15)	−0.11605 (11)	0.0222 (4)
O14	0.03594 (15)	0.66346 (14)	−0.07400 (11)	0.0207 (4)
N1	0.24219 (18)	0.73151 (16)	−0.05638 (13)	0.0177 (4)
N2	0.28913 (18)	0.95256 (16)	0.16457 (14)	0.0188 (4)
N3	0.47675 (17)	0.61226 (18)	0.25676 (13)	0.0201 (5)
N4	0.23728 (17)	0.63548 (16)	0.26057 (12)	0.0156 (4)
N5	0.03468 (16)	0.97105 (16)	0.14805 (12)	0.0145 (4)
N6	−0.01364 (16)	0.72147 (16)	−0.05854 (12)	0.0151 (4)
N7	0.38188 (17)	0.44889 (17)	−0.02653 (13)	0.0167 (4)
N8	0.42064 (17)	0.18730 (16)	−0.12895 (13)	0.0182 (4)
N9	0.14357 (17)	0.45352 (16)	−0.01727 (13)	0.0155 (4)
N10	0.16869 (17)	0.18438 (16)	−0.12015 (13)	0.0164 (4)
C1	0.36812 (19)	0.66259 (19)	0.09907 (15)	0.0151 (5)
C2	0.2942 (2)	0.74497 (19)	0.03559 (15)	0.0150 (5)
C3	0.2697 (2)	0.83773 (19)	0.05639 (16)	0.0150 (5)
C4	0.3163 (2)	0.85604 (19)	0.14258 (15)	0.0160 (5)
C5	0.3855 (2)	0.7816 (2)	0.20765 (15)	0.0167 (5)
C6	0.40758 (19)	0.68912 (19)	0.18603 (15)	0.0153 (5)
C7	0.11889 (19)	0.66947 (18)	0.10114 (14)	0.0134 (4)
C8	0.16099 (19)	0.70677 (18)	0.18645 (14)	0.0132 (5)
C9	0.13790 (19)	0.80214 (18)	0.20366 (14)	0.0129 (4)
C10	0.06265 (19)	0.86932 (18)	0.13282 (14)	0.0130 (4)
C11	0.01259 (19)	0.84061 (19)	0.04730 (15)	0.0136 (4)
C12	0.04082 (19)	0.74489 (18)	0.03258 (14)	0.0127 (4)
C13	0.4534 (2)	0.3707 (2)	0.02757 (16)	0.0198 (5)
C14	0.4677 (2)	0.2829 (2)	−0.00367 (16)	0.0193 (5)
C15	0.40828 (19)	0.27211 (18)	−0.09522 (15)	0.0144 (5)
C16	0.3346 (2)	0.35630 (19)	−0.14941 (15)	0.0156 (5)
C17	0.3240 (2)	0.4413 (2)	−0.11348 (16)	0.0171 (5)
C18	0.4867 (2)	0.0954 (2)	−0.07631 (19)	0.0224 (5)
C19	0.3557 (2)	0.1779 (2)	−0.22376 (17)	0.0225 (6)
C20	0.2132 (2)	0.3746 (2)	0.03694 (15)	0.0169 (5)
C21	0.2242 (2)	0.28440 (19)	0.00589 (15)	0.0156 (5)
C22	0.16143 (19)	0.27205 (18)	−0.08626 (15)	0.0136 (5)
C23	0.0910 (2)	0.35763 (19)	−0.14046 (15)	0.0148 (5)
C24	0.0844 (2)	0.4453 (2)	−0.10418 (16)	0.0170 (5)
C25	0.2392 (2)	0.0953 (2)	−0.06362 (18)	0.0224 (5)
C26	0.1053 (2)	0.1760 (2)	−0.21508 (17)	0.0199 (5)
H'	0.377 (2)	0.503 (2)	−0.0034 (18)	0.021 (7)*
H''	0.136 (2)	0.510 (2)	0.0056 (17)	0.017 (7)*
H3	0.219 (2)	0.887 (2)	0.0133 (19)	0.025 (8)*
H5	0.420 (2)	0.792 (2)	0.2676 (18)	0.015 (7)*
H9	0.1741 (19)	0.8207 (18)	0.2632 (15)	0.003 (5)*
H11	−0.039 (2)	0.887 (2)	0.0004 (18)	0.015 (7)*
H13	0.492 (3)	0.382 (2)	0.088 (2)	0.027 (8)*
H14	0.518 (2)	0.233 (2)	0.0368 (19)	0.026 (8)*
H16	0.290 (2)	0.355 (2)	−0.2104 (17)	0.010 (6)*
H17	0.276 (2)	0.497 (2)	−0.1480 (17)	0.016 (7)*
H18A	0.508 (3)	0.058 (3)	−0.105 (3)	0.058 (12)*
H18B	0.442 (3)	0.050 (3)	−0.072 (2)	0.040 (9)*
H18C	0.558 (3)	0.114 (2)	−0.017 (2)	0.030 (8)*
H19A	0.385 (3)	0.127 (3)	−0.232 (2)	0.039 (9)*
H19B	0.278 (3)	0.170 (3)	−0.254 (2)	0.038 (9)*
H19C	0.366 (3)	0.243 (3)	−0.250 (2)	0.049 (10)*
H20	0.257 (2)	0.386 (2)	0.0981 (17)	0.013 (6)*
H21	0.273 (3)	0.231 (2)	0.045 (2)	0.030 (8)*
H23	0.047 (2)	0.357 (2)	−0.2026 (16)	0.008 (6)*
H24	0.037 (2)	0.502 (2)	−0.1373 (18)	0.022 (7)*
H25A	0.222 (3)	0.037 (3)	−0.101 (2)	0.029 (8)*
H25B	0.221 (2)	0.072 (2)	−0.0273 (19)	0.024 (7)*
H25C	0.324 (3)	0.116 (3)	−0.022 (2)	0.037 (9)*
H26A	0.026 (3)	0.173 (2)	−0.245 (2)	0.034 (9)*
H26B	0.129 (2)	0.113 (2)	−0.2246 (19)	0.026 (8)*
H26C	0.123 (3)	0.231 (2)	−0.238 (2)	0.028 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0245 (9)	0.0200 (9)	0.0185 (8)	0.0055 (7)	0.0138 (8)	0.0009 (7)
O2	0.0313 (10)	0.0178 (9)	0.0192 (8)	0.0022 (8)	0.0168 (8)	−0.0034 (7)
O3	0.0595 (14)	0.0208 (10)	0.0234 (9)	0.0098 (9)	0.0299 (10)	0.0082 (8)
O4	0.0330 (11)	0.0198 (10)	0.0321 (10)	0.0044 (8)	0.0225 (9)	−0.0011 (8)
O5	0.0320 (10)	0.0308 (11)	0.0250 (9)	−0.0062 (8)	0.0218 (9)	−0.0121 (8)
O6	0.0263 (11)	0.0451 (13)	0.0160 (9)	0.0010 (9)	0.0031 (8)	0.0011 (9)
O7	0.0355 (11)	0.0178 (10)	0.0297 (10)	0.0042 (8)	0.0233 (9)	0.0081 (8)
O8	0.0268 (9)	0.0167 (9)	0.0165 (8)	0.0035 (7)	0.0146 (8)	−0.0017 (7)
O9	0.0334 (10)	0.0141 (9)	0.0236 (9)	−0.0003 (8)	0.0177 (9)	0.0041 (7)
O10	0.0193 (9)	0.0345 (11)	0.0142 (8)	−0.0050 (8)	0.0030 (8)	0.0023 (8)
O11	0.0293 (10)	0.0249 (10)	0.0148 (8)	0.0021 (8)	0.0134 (8)	−0.0054 (7)
O12	0.0294 (10)	0.0188 (9)	0.0193 (9)	0.0055 (8)	0.0165 (8)	0.0020 (7)
O13	0.0170 (9)	0.0308 (10)	0.0119 (8)	0.0030 (7)	0.0061 (7)	−0.0027 (7)
O14	0.0286 (10)	0.0220 (9)	0.0182 (8)	0.0064 (8)	0.0182 (8)	−0.0015 (7)
N1	0.0255 (11)	0.0167 (11)	0.0189 (10)	0.0007 (8)	0.0179 (9)	0.0011 (8)
N2	0.0208 (10)	0.0173 (11)	0.0239 (11)	−0.0068 (8)	0.0170 (10)	−0.0075 (9)
N3	0.0171 (10)	0.0262 (12)	0.0182 (10)	−0.0001 (9)	0.0119 (9)	0.0040 (9)
N4	0.0193 (10)	0.0186 (11)	0.0122 (9)	0.0010 (8)	0.0117 (9)	0.0008 (8)
N5	0.0158 (10)	0.0162 (10)	0.0142 (9)	−0.0034 (8)	0.0108 (8)	−0.0021 (8)
N6	0.0159 (10)	0.0160 (10)	0.0125 (9)	−0.0019 (8)	0.0087 (8)	−0.0009 (8)
N7	0.0196 (10)	0.0156 (10)	0.0189 (10)	−0.0012 (8)	0.0141 (9)	−0.0017 (8)
N8	0.0194 (10)	0.0169 (10)	0.0183 (10)	0.0039 (8)	0.0121 (9)	0.0012 (8)
N9	0.0192 (10)	0.0138 (10)	0.0165 (10)	−0.0008 (8)	0.0128 (9)	−0.0042 (8)
N10	0.0221 (10)	0.0148 (10)	0.0178 (10)	0.0003 (8)	0.0152 (9)	−0.0011 (8)
C1	0.0166 (11)	0.0156 (12)	0.0153 (11)	−0.0054 (9)	0.0114 (10)	−0.0029 (9)
C2	0.0166 (11)	0.0180 (12)	0.0144 (11)	−0.0031 (9)	0.0118 (10)	−0.0016 (9)
C3	0.0166 (11)	0.0120 (11)	0.0185 (11)	−0.0020 (9)	0.0122 (10)	0.0007 (9)
C4	0.0180 (11)	0.0163 (12)	0.0191 (11)	−0.0041 (9)	0.0144 (10)	−0.0037 (9)
C5	0.0148 (11)	0.0242 (13)	0.0135 (11)	−0.0069 (9)	0.0102 (10)	−0.0050 (9)
C6	0.0125 (11)	0.0181 (12)	0.0159 (11)	−0.0031 (9)	0.0094 (10)	0.0011 (9)
C7	0.0140 (11)	0.0161 (11)	0.0121 (10)	−0.0030 (9)	0.0093 (9)	−0.0018 (9)
C8	0.0124 (11)	0.0171 (12)	0.0109 (10)	−0.0039 (9)	0.0079 (9)	−0.0001 (9)
C9	0.0154 (11)	0.0173 (12)	0.0093 (10)	−0.0054 (9)	0.0094 (9)	−0.0035 (9)
C10	0.0147 (11)	0.0133 (11)	0.0146 (11)	−0.0042 (9)	0.0112 (9)	−0.0037 (9)
C11	0.0128 (11)	0.0150 (11)	0.0137 (10)	−0.0022 (9)	0.0088 (9)	0.0002 (9)
C12	0.0128 (10)	0.0157 (11)	0.0104 (10)	−0.0032 (9)	0.0077 (9)	−0.0028 (9)
C13	0.0208 (12)	0.0242 (14)	0.0141 (11)	−0.0023 (10)	0.0111 (10)	0.0008 (10)
C14	0.0188 (12)	0.0191 (13)	0.0172 (12)	0.0024 (10)	0.0103 (11)	0.0050 (10)
C15	0.0148 (11)	0.0131 (11)	0.0182 (11)	−0.0010 (9)	0.0119 (10)	0.0032 (9)
C16	0.0174 (12)	0.0159 (12)	0.0154 (11)	0.0012 (9)	0.0114 (10)	0.0028 (9)
C17	0.0193 (12)	0.0149 (12)	0.0182 (12)	0.0019 (10)	0.0126 (11)	0.0054 (9)
C18	0.0242 (14)	0.0151 (13)	0.0270 (14)	0.0032 (10)	0.0161 (13)	0.0040 (11)
C19	0.0246 (14)	0.0231 (14)	0.0207 (12)	0.0073 (11)	0.0150 (12)	−0.0016 (11)
C20	0.0186 (12)	0.0207 (13)	0.0122 (11)	−0.0036 (9)	0.0103 (10)	−0.0008 (9)
C21	0.0169 (11)	0.0153 (12)	0.0159 (11)	0.0014 (9)	0.0112 (10)	0.0033 (9)
C22	0.0149 (11)	0.0135 (11)	0.0177 (11)	−0.0032 (9)	0.0129 (10)	−0.0005 (9)
C23	0.0171 (11)	0.0176 (12)	0.0122 (11)	−0.0034 (9)	0.0106 (10)	0.0003 (9)
C24	0.0174 (12)	0.0147 (12)	0.0196 (12)	−0.0010 (9)	0.0122 (10)	0.0001 (9)
C25	0.0302 (15)	0.0148 (13)	0.0273 (13)	0.0050 (11)	0.0208 (13)	0.0030 (11)
C26	0.0275 (14)	0.0184 (13)	0.0215 (12)	−0.0010 (11)	0.0192 (12)	−0.0052 (10)

Geometric parameters (Å, º) top

O1—C1	1.235 (3)	C5—C6	1.358 (3)
O2—N1	1.224 (3)	C5—H5	0.95 (3)
O3—N1	1.226 (3)	C7—C12	1.445 (3)
O4—N2	1.223 (3)	C7—C8	1.446 (3)
O5—N2	1.232 (3)	C8—C9	1.358 (3)
O6—N3	1.230 (3)	C9—C10	1.391 (3)
O7—N3	1.215 (3)	C9—H9	0.96 (2)
O8—C7	1.240 (3)	C10—C11	1.385 (3)
O9—N4	1.218 (3)	C11—C12	1.375 (3)
O10—N4	1.218 (3)	C11—H11	0.94 (3)
O11—N5	1.228 (2)	C13—C14	1.353 (4)
O12—N5	1.225 (3)	C13—H13	0.95 (3)
O13—N6	1.221 (3)	C14—C15	1.419 (3)
O14—N6	1.225 (3)	C14—H14	0.92 (3)
N1—C2	1.454 (3)	C15—C16	1.412 (3)
N2—C4	1.441 (3)	C16—C17	1.353 (3)
N3—C6	1.454 (3)	C16—H16	0.93 (2)
N4—C8	1.457 (3)	C17—H17	0.93 (3)
N5—C10	1.444 (3)	C18—H18A	0.95 (4)
N6—C12	1.451 (3)	C18—H18B	0.94 (4)
N7—C17	1.340 (3)	C18—H18C	0.98 (3)
N7—C13	1.345 (3)	C19—H19A	0.85 (4)
N7—H'	0.86 (3)	C19—H19B	0.93 (3)
N8—C15	1.337 (3)	C19—H19C	1.04 (4)
N8—C18	1.448 (3)	C20—C21	1.354 (3)
N8—C19	1.458 (3)	C20—H20	0.94 (3)
N9—C24	1.337 (3)	C21—C22	1.422 (3)
N9—C20	1.344 (3)	C21—H21	0.93 (3)
N9—H''	0.89 (3)	C22—C23	1.411 (3)
N10—C22	1.335 (3)	C23—C24	1.358 (3)
N10—C25	1.458 (3)	C23—H23	0.95 (2)
N10—C26	1.463 (3)	C24—H24	0.92 (3)
C1—C6	1.451 (3)	C25—H25A	0.96 (3)
C1—C2	1.453 (3)	C25—H25B	0.97 (3)
C2—C3	1.370 (3)	C25—H25C	1.03 (3)
C3—C4	1.382 (3)	C26—H26A	0.95 (3)
C3—H3	0.93 (3)	C26—H26B	0.94 (3)
C4—C5	1.381 (3)	C26—H26C	0.95 (3)

O2—N1—O3	122.4 (2)	C12—C11—C10	119.1 (2)
O2—N1—C2	119.45 (19)	C12—C11—H11	121.2 (16)
O3—N1—C2	118.2 (2)	C10—C11—H11	119.7 (16)
O4—N2—O5	123.5 (2)	C11—C12—C7	124.1 (2)
O4—N2—C4	118.7 (2)	C11—C12—N6	115.8 (2)
O5—N2—C4	117.8 (2)	C7—C12—N6	120.1 (2)
O7—N3—O6	123.1 (2)	N7—C13—C14	121.6 (2)
O7—N3—C6	119.1 (2)	N7—C13—H13	114.9 (18)
O6—N3—C6	117.8 (2)	C14—C13—H13	123.6 (18)
O9—N4—O10	123.4 (2)	C13—C14—C15	120.3 (2)
O9—N4—C8	118.23 (19)	C13—C14—H14	117.3 (18)
O10—N4—C8	118.3 (2)	C15—C14—H14	122.4 (18)
O12—N5—O11	123.6 (2)	N8—C15—C16	121.5 (2)
O12—N5—C10	118.45 (18)	N8—C15—C14	122.4 (2)
O11—N5—C10	117.91 (19)	C16—C15—C14	116.2 (2)
O13—N6—O14	123.37 (19)	C17—C16—C15	120.2 (2)
O13—N6—C12	117.95 (19)	C17—C16—H16	117.0 (16)
O14—N6—C12	118.67 (19)	C15—C16—H16	122.7 (16)
C17—N7—C13	119.9 (2)	N7—C17—C16	121.9 (2)
C17—N7—H'	122.2 (18)	N7—C17—H17	116.8 (16)
C13—N7—H'	117.9 (18)	C16—C17—H17	121.3 (16)
C15—N8—C18	122.6 (2)	N8—C18—H18A	108 (2)
C15—N8—C19	120.7 (2)	N8—C18—H18B	110 (2)
C18—N8—C19	116.3 (2)	H18A—C18—H18B	108 (3)
C24—N9—C20	120.3 (2)	N8—C18—H18C	113.1 (18)
C24—N9—H''	120.9 (17)	H18A—C18—H18C	106 (3)
C20—N9—H''	118.9 (17)	H18B—C18—H18C	111 (3)
C22—N10—C25	120.8 (2)	N8—C19—H19A	107 (2)
C22—N10—C26	120.3 (2)	N8—C19—H19B	112 (2)
C25—N10—C26	118.9 (2)	H19A—C19—H19B	113 (3)
O1—C1—C6	122.6 (2)	N8—C19—H19C	112.5 (19)
O1—C1—C2	126.2 (2)	H19A—C19—H19C	104 (3)
C6—C1—C2	111.1 (2)	H19B—C19—H19C	108 (3)
C3—C2—C1	124.2 (2)	N9—C20—C21	121.7 (2)
C3—C2—N1	116.2 (2)	N9—C20—H20	117.1 (16)
C1—C2—N1	119.6 (2)	C21—C20—H20	121.2 (16)
C2—C3—C4	119.4 (2)	C20—C21—C22	119.8 (2)
C2—C3—H3	121.4 (18)	C20—C21—H21	119.8 (19)
C4—C3—H3	119.1 (18)	C22—C21—H21	120.5 (19)
C5—C4—C3	121.0 (2)	N10—C22—C23	121.4 (2)
C5—C4—N2	119.3 (2)	N10—C22—C21	122.0 (2)
C3—C4—N2	119.6 (2)	C23—C22—C21	116.6 (2)
C6—C5—C4	119.1 (2)	C24—C23—C22	120.1 (2)
C6—C5—H5	117.6 (16)	C24—C23—H23	117.3 (15)
C4—C5—H5	123.3 (16)	C22—C23—H23	122.6 (15)
C5—C6—C1	125.0 (2)	N9—C24—C23	121.6 (2)
C5—C6—N3	116.3 (2)	N9—C24—H24	115.3 (18)
C1—C6—N3	118.6 (2)	C23—C24—H24	123.0 (18)
O8—C7—C12	126.8 (2)	N10—C25—H25A	107.4 (18)
O8—C7—C8	122.0 (2)	N10—C25—H25B	112.7 (17)
C12—C7—C8	111.2 (2)	H25A—C25—H25B	106 (2)
C9—C8—C7	126.1 (2)	N10—C25—H25C	110.4 (18)
C9—C8—N4	117.60 (19)	H25A—C25—H25C	113 (3)
C7—C8—N4	116.3 (2)	H25B—C25—H25C	108 (2)
C8—C9—C10	117.8 (2)	N10—C26—H26A	109.2 (19)
C8—C9—H9	119.3 (14)	N10—C26—H26B	107.2 (18)
C10—C9—H9	122.8 (14)	H26A—C26—H26B	110 (3)
C11—C10—C9	121.5 (2)	N10—C26—H26C	113.3 (18)
C11—C10—N5	118.9 (2)	H26A—C26—H26C	111 (3)
C9—C10—N5	119.65 (19)	H26B—C26—H26C	105 (2)

O1—C1—C2—C3	−173.6 (2)	O12—N5—C10—C11	−5.6 (3)
C6—C1—C2—C3	3.0 (3)	O11—N5—C10—C11	174.2 (2)
O1—C1—C2—N1	5.7 (4)	O12—N5—C10—C9	175.0 (2)
C6—C1—C2—N1	−177.75 (19)	O11—N5—C10—C9	−5.2 (3)
O2—N1—C2—C3	−163.2 (2)	C9—C10—C11—C12	−2.1 (3)
O3—N1—C2—C3	16.1 (3)	N5—C10—C11—C12	178.57 (19)
O2—N1—C2—C1	17.4 (3)	C10—C11—C12—C7	1.3 (3)
O3—N1—C2—C1	−163.2 (2)	C10—C11—C12—N6	−178.93 (19)
C1—C2—C3—C4	−0.6 (4)	O8—C7—C12—C11	−179.0 (2)
N1—C2—C3—C4	−179.9 (2)	C8—C7—C12—C11	1.4 (3)
C2—C3—C4—C5	−1.0 (3)	O8—C7—C12—N6	1.2 (4)
C2—C3—C4—N2	−178.8 (2)	C8—C7—C12—N6	−178.40 (19)
O4—N2—C4—C5	175.9 (2)	O13—N6—C12—C11	−27.1 (3)
O5—N2—C4—C5	−4.6 (3)	O14—N6—C12—C11	152.0 (2)
O4—N2—C4—C3	−6.2 (3)	O13—N6—C12—C7	152.7 (2)
O5—N2—C4—C3	173.3 (2)	O14—N6—C12—C7	−28.3 (3)
C3—C4—C5—C6	−0.2 (3)	C17—N7—C13—C14	−0.9 (4)
N2—C4—C5—C6	177.6 (2)	N7—C13—C14—C15	1.2 (4)
C4—C5—C6—C1	3.1 (4)	C18—N8—C15—C16	−173.7 (2)
C4—C5—C6—N3	−177.3 (2)	C19—N8—C15—C16	−1.6 (3)
O1—C1—C6—C5	172.4 (2)	C18—N8—C15—C14	6.1 (4)
C2—C1—C6—C5	−4.2 (3)	C19—N8—C15—C14	178.3 (2)
O1—C1—C6—N3	−7.2 (3)	C13—C14—C15—N8	179.3 (2)
C2—C1—C6—N3	176.10 (19)	C13—C14—C15—C16	−0.8 (3)
O7—N3—C6—C5	148.0 (2)	N8—C15—C16—C17	−179.8 (2)
O6—N3—C6—C5	−30.4 (3)	C14—C15—C16—C17	0.3 (3)
O7—N3—C6—C1	−32.3 (3)	C13—N7—C17—C16	0.4 (4)
O6—N3—C6—C1	149.2 (2)	C15—C16—C17—N7	−0.1 (4)
O8—C7—C8—C9	176.6 (2)	C24—N9—C20—C21	−1.3 (4)
C12—C7—C8—C9	−3.7 (3)	N9—C20—C21—C22	0.5 (4)
O8—C7—C8—N4	−1.9 (3)	C25—N10—C22—C23	−178.1 (2)
C12—C7—C8—N4	177.74 (19)	C26—N10—C22—C23	1.6 (3)
O9—N4—C8—C9	125.8 (2)	C25—N10—C22—C21	2.1 (3)
O10—N4—C8—C9	−54.2 (3)	C26—N10—C22—C21	−178.2 (2)
O9—N4—C8—C7	−55.5 (3)	C20—C21—C22—N10	−179.6 (2)
O10—N4—C8—C7	124.5 (2)	C20—C21—C22—C23	0.6 (3)
C7—C8—C9—C10	3.2 (3)	N10—C22—C23—C24	179.3 (2)
N4—C8—C9—C10	−178.3 (2)	C21—C22—C23—C24	−0.9 (3)
C8—C9—C10—C11	−0.1 (3)	C20—N9—C24—C23	1.0 (4)
C8—C9—C10—N5	179.3 (2)	C22—C23—C24—N9	0.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H′···O1	0.86 (3)	1.83 (3)	2.640 (3)	156 (3)
N7—H′···O2	0.86 (3)	2.41 (3)	2.986 (3)	125 (2)
N9—H′′···O8	0.89 (3)	1.84 (3)	2.669 (3)	154 (2)
N9—H′′···O14	0.89 (3)	2.34 (3)	2.934 (3)	124 (2)
C3—H3···O3	0.93 (3)	2.38 (3)	2.661 (3)	97 (2)
C3—H3···O4	0.93 (3)	2.42 (3)	2.718 (3)	99 (2)
C5—H5···O5	0.95 (3)	2.45 (3)	2.696 (3)	94.2 (17)
C5—H5···O6	0.95 (3)	2.37 (3)	2.701 (3)	99.6 (18)
C5—H5···O10	0.95 (3)	2.72 (3)	3.237 (3)	114.6 (19)
C9—H9···O10	0.96 (2)	2.68 (2)	2.860 (3)	91.0 (15)
C9—H9···O11	0.96 (2)	2.47 (2)	2.712 (3)	94.1 (15)
C11—H11···O12	0.94 (3)	2.40 (3)	2.702 (3)	98.2 (18)
C11—H11···O13	0.94 (3)	2.41 (3)	2.681 (3)	96.0 (18)
C13—H13···O1	0.95 (3)	2.87 (3)	3.201 (3)	102 (2)
C17—H17···O2	0.93 (3)	2.51 (3)	3.090 (3)	121 (2)
C20—H20···O8	0.94 (3)	2.94 (3)	3.232 (3)	99.2 (17)
C24—H24···O14	0.92 (3)	2.40 (3)	3.007 (3)	123 (2)
C11—H11···O4ⁱ	0.94 (3)	2.56 (3)	3.430 (3)	153 (2)
C11—H11···O12ⁱ	0.94 (3)	2.66 (3)	3.195 (3)	116.7 (19)
C9—H9···O2ⁱⁱ	0.96 (2)	2.56 (2)	3.501 (3)	169.5 (19)
C9—H9···O3ⁱⁱ	0.96 (2)	2.89 (2)	3.552 (3)	127.7 (17)
C14—H14···O10ⁱⁱⁱ	0.92 (3)	2.32 (3)	3.186 (3)	156 (2)
C21—H21···O6ⁱⁱⁱ	0.93 (3)	2.45 (3)	3.328 (3)	159 (3)
C13—H13···O5ⁱⁱⁱ	0.95 (3)	2.86 (3)	3.733 (3)	153 (2)
C25—H25C···O6ⁱⁱⁱ	1.03 (3)	2.94 (3)	3.579 (3)	121 (2)
C17—H17···O5^iv	0.93 (3)	2.78 (3)	3.140 (3)	104.3 (19)
C23—H23···O11^iv	0.95 (2)	2.58 (2)	3.163 (3)	119.7 (18)
C17—H17···O11^iv	0.93 (3)	2.45 (3)	3.156 (3)	133 (2)
C16—H16···O5^iv	0.93 (2)	2.68 (3)	3.098 (3)	107.9 (18)
C19—H19B···O13^v	0.93 (3)	2.48 (3)	3.188 (3)	133 (3)
C16—H16···O13^v	0.93 (2)	2.94 (3)	3.784 (3)	151 (2)
C26—H26C···O13^v	0.95 (3)	2.77 (3)	3.524 (3)	137 (2)
C26—H26C···O14^v	0.95 (3)	2.98 (3)	3.245 (3)	97 (2)
C19—H19A···O7^vi	0.85 (4)	2.42 (4)	3.273 (3)	177 (3)
C26—H26B···O9^vi	0.94 (3)	2.46 (3)	3.398 (3)	176 (2)
C18—H18A···O7^vi	0.95 (4)	2.84 (4)	3.695 (4)	151 (3)
C25—H25A···O9^vi	0.96 (3)	2.85 (3)	3.706 (3)	149 (2)
C18—H18C···O3^vii	0.98 (3)	2.95 (3)	3.857 (4)	153 (2)
C25—H25B···O12^viii	0.97 (3)	2.74 (3)	3.406 (3)	126 (2)
C24—H24···O9^viii	0.92 (3)	2.88 (3)	3.380 (3)	116 (2)
C26—H26A···O11^viii	0.95 (3)	2.76 (3)	3.363 (3)	122 (2)
C25—H25A···O3^ix	0.96 (3)	2.87 (3)	3.651 (3)	139 (2)
C25—H25B···O4^ix	0.97 (3)	2.64 (3)	3.578 (3)	164 (2)

Symmetry codes: (i) −x, −y+2, −z; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) x, −y+3/2, z−1/2; (v) −x, y−1/2, −z−1/2; (vi) x, −y+1/2, z−1/2; (vii) −x+1, −y+1, −z; (viii) −x, −y+1, −z; (ix) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₇H₁₁N₂·C₆H₂N₃O₇
M_r	351.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.274 (4), 12.617 (3), 19.795 (4)
β (°)	129.996 (13)
V (Å³)	2922.4 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.50 × 0.40 × 0.20

Data collection
Diffractometer	CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.937, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	24887, 6947, 5744
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.155, 1.20
No. of reflections	6947
No. of parameters	555
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.32

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top

O1—C1	1.235 (3)	N2—C4	1.441 (3)
O2—N1	1.224 (3)	N3—C6	1.454 (3)
O3—N1	1.226 (3)	N4—C8	1.457 (3)
O4—N2	1.223 (3)	N5—C10	1.444 (3)
O5—N2	1.232 (3)	N6—C12	1.451 (3)
O6—N3	1.230 (3)	N7—C17	1.340 (3)
O7—N3	1.215 (3)	N7—C13	1.345 (3)
O8—C7	1.240 (3)	N8—C15	1.337 (3)
O9—N4	1.218 (3)	N8—C18	1.448 (3)
O10—N4	1.218 (3)	N8—C19	1.458 (3)
O11—N5	1.228 (2)	N9—C24	1.337 (3)
O12—N5	1.225 (3)	N9—C20	1.344 (3)
O13—N6	1.221 (3)	N10—C22	1.335 (3)
O14—N6	1.225 (3)	N10—C25	1.458 (3)
N1—C2	1.454 (3)	N10—C26	1.463 (3)

O2—N1—O3	122.4 (2)	O12—N5—C10	118.45 (18)
O2—N1—C2	119.45 (19)	O11—N5—C10	117.91 (19)
O3—N1—C2	118.2 (2)	O13—N6—O14	123.37 (19)
O4—N2—O5	123.5 (2)	O13—N6—C12	117.95 (19)
O4—N2—C4	118.7 (2)	O14—N6—C12	118.67 (19)
O5—N2—C4	117.8 (2)	C17—N7—C13	119.9 (2)
O7—N3—O6	123.1 (2)	C15—N8—C18	122.6 (2)
O7—N3—C6	119.1 (2)	C15—N8—C19	120.7 (2)
O6—N3—C6	117.8 (2)	C18—N8—C19	116.3 (2)
O9—N4—O10	123.4 (2)	C24—N9—C20	120.3 (2)
O9—N4—C8	118.23 (19)	C22—N10—C25	120.8 (2)
O10—N4—C8	118.3 (2)	C22—N10—C26	120.3 (2)
O12—N5—O11	123.6 (2)	C25—N10—C26	118.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H'···O1	0.86 (3)	1.83 (3)	2.640 (3)	156 (3)
N7—H'···O2	0.86 (3)	2.41 (3)	2.986 (3)	125 (2)
N9—H''···O8	0.89 (3)	1.84 (3)	2.669 (3)	154 (2)
N9—H''···O14	0.89 (3)	2.34 (3)	2.934 (3)	124 (2)
C3—H3···O3	0.93 (3)	2.38 (3)	2.661 (3)	97 (2)
C3—H3···O4	0.93 (3)	2.42 (3)	2.718 (3)	99 (2)
C5—H5···O5	0.95 (3)	2.45 (3)	2.696 (3)	94.2 (17)
C5—H5···O6	0.95 (3)	2.37 (3)	2.701 (3)	99.6 (18)
C5—H5···O10	0.95 (3)	2.72 (3)	3.237 (3)	114.6 (19)
C9—H9···O10	0.96 (2)	2.68 (2)	2.860 (3)	91.0 (15)
C9—H9···O11	0.96 (2)	2.47 (2)	2.712 (3)	94.1 (15)
C11—H11···O12	0.94 (3)	2.40 (3)	2.702 (3)	98.2 (18)
C11—H11···O13	0.94 (3)	2.41 (3)	2.681 (3)	96.0 (18)
C13—H13···O1	0.95 (3)	2.87 (3)	3.201 (3)	102 (2)
C17—H17···O2	0.93 (3)	2.51 (3)	3.090 (3)	121 (2)
C20—H20···O8	0.94 (3)	2.94 (3)	3.232 (3)	99.2 (17)
C24—H24···O14	0.92 (3)	2.40 (3)	3.007 (3)	123 (2)
C11—H11···O4ⁱ	0.94 (3)	2.56 (3)	3.430 (3)	153 (2)
C11—H11···O12ⁱ	0.94 (3)	2.66 (3)	3.195 (3)	116.7 (19)
C9—H9···O2ⁱⁱ	0.96 (2)	2.56 (2)	3.501 (3)	169.5 (19)
C9—H9···O3ⁱⁱ	0.96 (2)	2.89 (2)	3.552 (3)	127.7 (17)
C14—H14···O10ⁱⁱⁱ	0.92 (3)	2.32 (3)	3.186 (3)	156 (2)
C21—H21···O6ⁱⁱⁱ	0.93 (3)	2.45 (3)	3.328 (3)	159 (3)
C13—H13···O5ⁱⁱⁱ	0.95 (3)	2.86 (3)	3.733 (3)	153 (2)
C25—H25C···O6ⁱⁱⁱ	1.03 (3)	2.94 (3)	3.579 (3)	121 (2)
C17—H17···O5^iv	0.93 (3)	2.78 (3)	3.140 (3)	104.3 (19)
C23—H23···O11^iv	0.95 (2)	2.58 (2)	3.163 (3)	119.7 (18)
C17—H17···O11^iv	0.93 (3)	2.45 (3)	3.156 (3)	133 (2)
C16—H16···O5^iv	0.93 (2)	2.68 (3)	3.098 (3)	107.9 (18)
C19—H19B···O13^v	0.93 (3)	2.48 (3)	3.188 (3)	133 (3)
C16—H16···O13^v	0.93 (2)	2.94 (3)	3.784 (3)	151 (2)
C26—H26C···O13^v	0.95 (3)	2.77 (3)	3.524 (3)	137 (2)
C26—H26C···O14^v	0.95 (3)	2.98 (3)	3.245 (3)	97 (2)
C19—H19A···O7^vi	0.85 (4)	2.42 (4)	3.273 (3)	177 (3)
C26—H26B···O9^vi	0.94 (3)	2.46 (3)	3.398 (3)	176 (2)
C18—H18A···O7^vi	0.95 (4)	2.84 (4)	3.695 (4)	151 (3)
C25—H25A···O9^vi	0.96 (3)	2.85 (3)	3.706 (3)	149 (2)
C18—H18C···O3^vii	0.98 (3)	2.95 (3)	3.857 (4)	153 (2)
C25—H25B···O12^viii	0.97 (3)	2.74 (3)	3.406 (3)	126 (2)
C24—H24···O9^viii	0.92 (3)	2.88 (3)	3.380 (3)	116 (2)
C26—H26A···O11^viii	0.95 (3)	2.76 (3)	3.363 (3)	122 (2)
C25—H25A···O3^ix	0.96 (3)	2.87 (3)	3.651 (3)	139 (2)
C25—H25B···O4^ix	0.97 (3)	2.64 (3)	3.578 (3)	164 (2)

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4-Di­methyl­amino­pyridinium picrate: supramolecular aggregation through extensive N—HO and C—HO interactions