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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012212/ci6222sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803012212/ci6222Isup2.hkl
Contains datablock I

CCDC reference: 217437

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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···O5iv and C17—H17···O5iv 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···O11iv and C17—H17···O5iv interactions constitute a pair of bifurcated donor bonds. The C17—H17···O11iv and C23—H23···O11iv interactions form a pair of bifurcated acceptor bonds. The C19—H19B.·O13v and C16—H16···O13v interactions form a pair of bifurcated acceptor bonds generating a ring of graph set R12(7).

The C26—H26C···O13v and C26—H26C···O14v interactions constitute a pair of bifurcated donor bonds generating a ring of graph set motif R21(4). The C19—H19B···O13v, C16—H16···O13v and C26—H26C···O13v interactions can be collectively termed as trifurcated acceptor bonds. The C19—H19A···O7vi and C18—H18A···O7vi interactions form a pair of bifurcated acceptor bonds generating a ring of graph set R12(6). The C25—H25A···O9vi and C26—H26B···O9vi interactions constitute a pair of bifurcated acceptor bonds generating a ring of graph set R12(6). The C25—H25B···O12viii and C26—H26A···O11viii interactions generate a fork motif (Vembu et al., 2003a) of graph set R22(8). The C26—H26A···O11viii and C24—H24···O9viii interactions generate a ring of graph set R22(14). Another R22(14) motif is formed by the C25—H25B···O12viii and C24—H24···O9viii interactions. The C25—H25A···O3ix and C25—H25B···O4ix 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.

Refinement top

H atoms were located from a difference Fourier map and both positional and isotropic displacement paramaters were refined. The ranges of C—H and N—H bond lengths are 0.92 (3)–1.04 (4) Å and 0.86 (3)–0.89 (3) Å, respectively and Uiso values range from 0.003 (5)–0.058 (12) Å2.

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
[Figure 1] Fig. 1. The contents of the asymmetric unit of (I), showing 50% probability displacement ellipsoids and, N—H···O and C—H···O interactions.
[Figure 2] Fig. 2. A view of the molecular packing of (I).
4-N,N-Dimethylaminopyridinium 2,4,6-trinitrophenolate top
Crystal data top
C7H11N2·C6H2N3O7F(000) = 1456
Mr = 351.28Dx = 1.597 Mg m3
Monoclinic, P21/cMelting point = 197–199 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.274 (4) ÅCell parameters from 5444 reflections
b = 12.617 (3) Åθ = 2.4–28.2°
c = 19.795 (4) ŵ = 0.13 mm1
β = 129.996 (13)°T = 100 K
V = 2922.4 (12) Å3Block, yellow
Z = 80.50 × 0.40 × 0.20 mm
Data collection top
CCD area detector
diffractometer
6947 independent reflections
Radiation source: fine-focus sealed tube5744 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
ϕ and ω scansθmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2019
Tmin = 0.937, Tmax = 0.974k = 1616
24887 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155All H-atom parameters refined
S = 1.20 w = 1/[σ2(Fo2) + (0.0449P)2 + 2.9161P]
where P = (Fo2 + 2Fc2)/3
6947 reflections(Δ/σ)max < 0.001
555 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C7H11N2·C6H2N3O7V = 2922.4 (12) Å3
Mr = 351.28Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.274 (4) ŵ = 0.13 mm1
b = 12.617 (3) ÅT = 100 K
c = 19.795 (4) Å0.50 × 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)
Tmin = 0.937, Tmax = 0.974Rint = 0.069
24887 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0720 restraints
wR(F2) = 0.155All H-atom parameters refined
S = 1.20Δρmax = 0.50 e Å3
6947 reflectionsΔρmin = 0.32 e Å3
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
xyzUiso*/Ueq
O10.39985 (15)0.58218 (14)0.08462 (11)0.0210 (4)
O20.23796 (16)0.64307 (14)0.08376 (11)0.0224 (4)
O30.20307 (19)0.81007 (15)0.10400 (12)0.0322 (5)
O40.23307 (16)1.02045 (15)0.10762 (12)0.0272 (4)
O50.32326 (16)0.96172 (15)0.24010 (12)0.0267 (4)
O60.54812 (17)0.64622 (18)0.33229 (12)0.0368 (5)
O70.46009 (16)0.51830 (14)0.23918 (12)0.0260 (4)
O80.14841 (15)0.58289 (13)0.09176 (11)0.0195 (4)
O90.20398 (16)0.54601 (14)0.25612 (12)0.0241 (4)
O100.33094 (15)0.66845 (16)0.32372 (11)0.0284 (4)
O110.07247 (16)0.99157 (14)0.22318 (11)0.0236 (4)
O120.02541 (16)1.03188 (14)0.08560 (11)0.0219 (4)
O130.10633 (14)0.76201 (15)0.11605 (11)0.0222 (4)
O140.03594 (15)0.66346 (14)0.07400 (11)0.0207 (4)
N10.24219 (18)0.73151 (16)0.05638 (13)0.0177 (4)
N20.28913 (18)0.95256 (16)0.16457 (14)0.0188 (4)
N30.47675 (17)0.61226 (18)0.25676 (13)0.0201 (5)
N40.23728 (17)0.63548 (16)0.26057 (12)0.0156 (4)
N50.03468 (16)0.97105 (16)0.14805 (12)0.0145 (4)
N60.01364 (16)0.72147 (16)0.05854 (12)0.0151 (4)
N70.38188 (17)0.44889 (17)0.02653 (13)0.0167 (4)
N80.42064 (17)0.18730 (16)0.12895 (13)0.0182 (4)
N90.14357 (17)0.45352 (16)0.01727 (13)0.0155 (4)
N100.16869 (17)0.18438 (16)0.12015 (13)0.0164 (4)
C10.36812 (19)0.66259 (19)0.09907 (15)0.0151 (5)
C20.2942 (2)0.74497 (19)0.03559 (15)0.0150 (5)
C30.2697 (2)0.83773 (19)0.05639 (16)0.0150 (5)
C40.3163 (2)0.85604 (19)0.14258 (15)0.0160 (5)
C50.3855 (2)0.7816 (2)0.20765 (15)0.0167 (5)
C60.40758 (19)0.68912 (19)0.18603 (15)0.0153 (5)
C70.11889 (19)0.66947 (18)0.10114 (14)0.0134 (4)
C80.16099 (19)0.70677 (18)0.18645 (14)0.0132 (5)
C90.13790 (19)0.80214 (18)0.20366 (14)0.0129 (4)
C100.06265 (19)0.86932 (18)0.13282 (14)0.0130 (4)
C110.01259 (19)0.84061 (19)0.04730 (15)0.0136 (4)
C120.04082 (19)0.74489 (18)0.03258 (14)0.0127 (4)
C130.4534 (2)0.3707 (2)0.02757 (16)0.0198 (5)
C140.4677 (2)0.2829 (2)0.00367 (16)0.0193 (5)
C150.40828 (19)0.27211 (18)0.09522 (15)0.0144 (5)
C160.3346 (2)0.35630 (19)0.14941 (15)0.0156 (5)
C170.3240 (2)0.4413 (2)0.11348 (16)0.0171 (5)
C180.4867 (2)0.0954 (2)0.07631 (19)0.0224 (5)
C190.3557 (2)0.1779 (2)0.22376 (17)0.0225 (6)
C200.2132 (2)0.3746 (2)0.03694 (15)0.0169 (5)
C210.2242 (2)0.28440 (19)0.00589 (15)0.0156 (5)
C220.16143 (19)0.27205 (18)0.08626 (15)0.0136 (5)
C230.0910 (2)0.35763 (19)0.14046 (15)0.0148 (5)
C240.0844 (2)0.4453 (2)0.10418 (16)0.0170 (5)
C250.2392 (2)0.0953 (2)0.06362 (18)0.0224 (5)
C260.1053 (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)*
H30.219 (2)0.887 (2)0.0133 (19)0.025 (8)*
H50.420 (2)0.792 (2)0.2676 (18)0.015 (7)*
H90.1741 (19)0.8207 (18)0.2632 (15)0.003 (5)*
H110.039 (2)0.887 (2)0.0004 (18)0.015 (7)*
H130.492 (3)0.382 (2)0.088 (2)0.027 (8)*
H140.518 (2)0.233 (2)0.0368 (19)0.026 (8)*
H160.290 (2)0.355 (2)0.2104 (17)0.010 (6)*
H170.276 (2)0.497 (2)0.1480 (17)0.016 (7)*
H18A0.508 (3)0.058 (3)0.105 (3)0.058 (12)*
H18B0.442 (3)0.050 (3)0.072 (2)0.040 (9)*
H18C0.558 (3)0.114 (2)0.017 (2)0.030 (8)*
H19A0.385 (3)0.127 (3)0.232 (2)0.039 (9)*
H19B0.278 (3)0.170 (3)0.254 (2)0.038 (9)*
H19C0.366 (3)0.243 (3)0.250 (2)0.049 (10)*
H200.257 (2)0.386 (2)0.0981 (17)0.013 (6)*
H210.273 (3)0.231 (2)0.045 (2)0.030 (8)*
H230.047 (2)0.357 (2)0.2026 (16)0.008 (6)*
H240.037 (2)0.502 (2)0.1373 (18)0.022 (7)*
H25A0.222 (3)0.037 (3)0.101 (2)0.029 (8)*
H25B0.221 (2)0.072 (2)0.0273 (19)0.024 (7)*
H25C0.324 (3)0.116 (3)0.022 (2)0.037 (9)*
H26A0.026 (3)0.173 (2)0.245 (2)0.034 (9)*
H26B0.129 (2)0.113 (2)0.2246 (19)0.026 (8)*
H26C0.123 (3)0.231 (2)0.238 (2)0.028 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0245 (9)0.0200 (9)0.0185 (8)0.0055 (7)0.0138 (8)0.0009 (7)
O20.0313 (10)0.0178 (9)0.0192 (8)0.0022 (8)0.0168 (8)0.0034 (7)
O30.0595 (14)0.0208 (10)0.0234 (9)0.0098 (9)0.0299 (10)0.0082 (8)
O40.0330 (11)0.0198 (10)0.0321 (10)0.0044 (8)0.0225 (9)0.0011 (8)
O50.0320 (10)0.0308 (11)0.0250 (9)0.0062 (8)0.0218 (9)0.0121 (8)
O60.0263 (11)0.0451 (13)0.0160 (9)0.0010 (9)0.0031 (8)0.0011 (9)
O70.0355 (11)0.0178 (10)0.0297 (10)0.0042 (8)0.0233 (9)0.0081 (8)
O80.0268 (9)0.0167 (9)0.0165 (8)0.0035 (7)0.0146 (8)0.0017 (7)
O90.0334 (10)0.0141 (9)0.0236 (9)0.0003 (8)0.0177 (9)0.0041 (7)
O100.0193 (9)0.0345 (11)0.0142 (8)0.0050 (8)0.0030 (8)0.0023 (8)
O110.0293 (10)0.0249 (10)0.0148 (8)0.0021 (8)0.0134 (8)0.0054 (7)
O120.0294 (10)0.0188 (9)0.0193 (9)0.0055 (8)0.0165 (8)0.0020 (7)
O130.0170 (9)0.0308 (10)0.0119 (8)0.0030 (7)0.0061 (7)0.0027 (7)
O140.0286 (10)0.0220 (9)0.0182 (8)0.0064 (8)0.0182 (8)0.0015 (7)
N10.0255 (11)0.0167 (11)0.0189 (10)0.0007 (8)0.0179 (9)0.0011 (8)
N20.0208 (10)0.0173 (11)0.0239 (11)0.0068 (8)0.0170 (10)0.0075 (9)
N30.0171 (10)0.0262 (12)0.0182 (10)0.0001 (9)0.0119 (9)0.0040 (9)
N40.0193 (10)0.0186 (11)0.0122 (9)0.0010 (8)0.0117 (9)0.0008 (8)
N50.0158 (10)0.0162 (10)0.0142 (9)0.0034 (8)0.0108 (8)0.0021 (8)
N60.0159 (10)0.0160 (10)0.0125 (9)0.0019 (8)0.0087 (8)0.0009 (8)
N70.0196 (10)0.0156 (10)0.0189 (10)0.0012 (8)0.0141 (9)0.0017 (8)
N80.0194 (10)0.0169 (10)0.0183 (10)0.0039 (8)0.0121 (9)0.0012 (8)
N90.0192 (10)0.0138 (10)0.0165 (10)0.0008 (8)0.0128 (9)0.0042 (8)
N100.0221 (10)0.0148 (10)0.0178 (10)0.0003 (8)0.0152 (9)0.0011 (8)
C10.0166 (11)0.0156 (12)0.0153 (11)0.0054 (9)0.0114 (10)0.0029 (9)
C20.0166 (11)0.0180 (12)0.0144 (11)0.0031 (9)0.0118 (10)0.0016 (9)
C30.0166 (11)0.0120 (11)0.0185 (11)0.0020 (9)0.0122 (10)0.0007 (9)
C40.0180 (11)0.0163 (12)0.0191 (11)0.0041 (9)0.0144 (10)0.0037 (9)
C50.0148 (11)0.0242 (13)0.0135 (11)0.0069 (9)0.0102 (10)0.0050 (9)
C60.0125 (11)0.0181 (12)0.0159 (11)0.0031 (9)0.0094 (10)0.0011 (9)
C70.0140 (11)0.0161 (11)0.0121 (10)0.0030 (9)0.0093 (9)0.0018 (9)
C80.0124 (11)0.0171 (12)0.0109 (10)0.0039 (9)0.0079 (9)0.0001 (9)
C90.0154 (11)0.0173 (12)0.0093 (10)0.0054 (9)0.0094 (9)0.0035 (9)
C100.0147 (11)0.0133 (11)0.0146 (11)0.0042 (9)0.0112 (9)0.0037 (9)
C110.0128 (11)0.0150 (11)0.0137 (10)0.0022 (9)0.0088 (9)0.0002 (9)
C120.0128 (10)0.0157 (11)0.0104 (10)0.0032 (9)0.0077 (9)0.0028 (9)
C130.0208 (12)0.0242 (14)0.0141 (11)0.0023 (10)0.0111 (10)0.0008 (10)
C140.0188 (12)0.0191 (13)0.0172 (12)0.0024 (10)0.0103 (11)0.0050 (10)
C150.0148 (11)0.0131 (11)0.0182 (11)0.0010 (9)0.0119 (10)0.0032 (9)
C160.0174 (12)0.0159 (12)0.0154 (11)0.0012 (9)0.0114 (10)0.0028 (9)
C170.0193 (12)0.0149 (12)0.0182 (12)0.0019 (10)0.0126 (11)0.0054 (9)
C180.0242 (14)0.0151 (13)0.0270 (14)0.0032 (10)0.0161 (13)0.0040 (11)
C190.0246 (14)0.0231 (14)0.0207 (12)0.0073 (11)0.0150 (12)0.0016 (11)
C200.0186 (12)0.0207 (13)0.0122 (11)0.0036 (9)0.0103 (10)0.0008 (9)
C210.0169 (11)0.0153 (12)0.0159 (11)0.0014 (9)0.0112 (10)0.0033 (9)
C220.0149 (11)0.0135 (11)0.0177 (11)0.0032 (9)0.0129 (10)0.0005 (9)
C230.0171 (11)0.0176 (12)0.0122 (11)0.0034 (9)0.0106 (10)0.0003 (9)
C240.0174 (12)0.0147 (12)0.0196 (12)0.0010 (9)0.0122 (10)0.0001 (9)
C250.0302 (15)0.0148 (13)0.0273 (13)0.0050 (11)0.0208 (13)0.0030 (11)
C260.0275 (14)0.0184 (13)0.0215 (12)0.0010 (11)0.0192 (12)0.0052 (10)
Geometric parameters (Å, º) top
O1—C11.235 (3)C5—C61.358 (3)
O2—N11.224 (3)C5—H50.95 (3)
O3—N11.226 (3)C7—C121.445 (3)
O4—N21.223 (3)C7—C81.446 (3)
O5—N21.232 (3)C8—C91.358 (3)
O6—N31.230 (3)C9—C101.391 (3)
O7—N31.215 (3)C9—H90.96 (2)
O8—C71.240 (3)C10—C111.385 (3)
O9—N41.218 (3)C11—C121.375 (3)
O10—N41.218 (3)C11—H110.94 (3)
O11—N51.228 (2)C13—C141.353 (4)
O12—N51.225 (3)C13—H130.95 (3)
O13—N61.221 (3)C14—C151.419 (3)
O14—N61.225 (3)C14—H140.92 (3)
N1—C21.454 (3)C15—C161.412 (3)
N2—C41.441 (3)C16—C171.353 (3)
N3—C61.454 (3)C16—H160.93 (2)
N4—C81.457 (3)C17—H170.93 (3)
N5—C101.444 (3)C18—H18A0.95 (4)
N6—C121.451 (3)C18—H18B0.94 (4)
N7—C171.340 (3)C18—H18C0.98 (3)
N7—C131.345 (3)C19—H19A0.85 (4)
N7—H'0.86 (3)C19—H19B0.93 (3)
N8—C151.337 (3)C19—H19C1.04 (4)
N8—C181.448 (3)C20—C211.354 (3)
N8—C191.458 (3)C20—H200.94 (3)
N9—C241.337 (3)C21—C221.422 (3)
N9—C201.344 (3)C21—H210.93 (3)
N9—H''0.89 (3)C22—C231.411 (3)
N10—C221.335 (3)C23—C241.358 (3)
N10—C251.458 (3)C23—H230.95 (2)
N10—C261.463 (3)C24—H240.92 (3)
C1—C61.451 (3)C25—H25A0.96 (3)
C1—C21.453 (3)C25—H25B0.97 (3)
C2—C31.370 (3)C25—H25C1.03 (3)
C3—C41.382 (3)C26—H26A0.95 (3)
C3—H30.93 (3)C26—H26B0.94 (3)
C4—C51.381 (3)C26—H26C0.95 (3)
O2—N1—O3122.4 (2)C12—C11—C10119.1 (2)
O2—N1—C2119.45 (19)C12—C11—H11121.2 (16)
O3—N1—C2118.2 (2)C10—C11—H11119.7 (16)
O4—N2—O5123.5 (2)C11—C12—C7124.1 (2)
O4—N2—C4118.7 (2)C11—C12—N6115.8 (2)
O5—N2—C4117.8 (2)C7—C12—N6120.1 (2)
O7—N3—O6123.1 (2)N7—C13—C14121.6 (2)
O7—N3—C6119.1 (2)N7—C13—H13114.9 (18)
O6—N3—C6117.8 (2)C14—C13—H13123.6 (18)
O9—N4—O10123.4 (2)C13—C14—C15120.3 (2)
O9—N4—C8118.23 (19)C13—C14—H14117.3 (18)
O10—N4—C8118.3 (2)C15—C14—H14122.4 (18)
O12—N5—O11123.6 (2)N8—C15—C16121.5 (2)
O12—N5—C10118.45 (18)N8—C15—C14122.4 (2)
O11—N5—C10117.91 (19)C16—C15—C14116.2 (2)
O13—N6—O14123.37 (19)C17—C16—C15120.2 (2)
O13—N6—C12117.95 (19)C17—C16—H16117.0 (16)
O14—N6—C12118.67 (19)C15—C16—H16122.7 (16)
C17—N7—C13119.9 (2)N7—C17—C16121.9 (2)
C17—N7—H'122.2 (18)N7—C17—H17116.8 (16)
C13—N7—H'117.9 (18)C16—C17—H17121.3 (16)
C15—N8—C18122.6 (2)N8—C18—H18A108 (2)
C15—N8—C19120.7 (2)N8—C18—H18B110 (2)
C18—N8—C19116.3 (2)H18A—C18—H18B108 (3)
C24—N9—C20120.3 (2)N8—C18—H18C113.1 (18)
C24—N9—H''120.9 (17)H18A—C18—H18C106 (3)
C20—N9—H''118.9 (17)H18B—C18—H18C111 (3)
C22—N10—C25120.8 (2)N8—C19—H19A107 (2)
C22—N10—C26120.3 (2)N8—C19—H19B112 (2)
C25—N10—C26118.9 (2)H19A—C19—H19B113 (3)
O1—C1—C6122.6 (2)N8—C19—H19C112.5 (19)
O1—C1—C2126.2 (2)H19A—C19—H19C104 (3)
C6—C1—C2111.1 (2)H19B—C19—H19C108 (3)
C3—C2—C1124.2 (2)N9—C20—C21121.7 (2)
C3—C2—N1116.2 (2)N9—C20—H20117.1 (16)
C1—C2—N1119.6 (2)C21—C20—H20121.2 (16)
C2—C3—C4119.4 (2)C20—C21—C22119.8 (2)
C2—C3—H3121.4 (18)C20—C21—H21119.8 (19)
C4—C3—H3119.1 (18)C22—C21—H21120.5 (19)
C5—C4—C3121.0 (2)N10—C22—C23121.4 (2)
C5—C4—N2119.3 (2)N10—C22—C21122.0 (2)
C3—C4—N2119.6 (2)C23—C22—C21116.6 (2)
C6—C5—C4119.1 (2)C24—C23—C22120.1 (2)
C6—C5—H5117.6 (16)C24—C23—H23117.3 (15)
C4—C5—H5123.3 (16)C22—C23—H23122.6 (15)
C5—C6—C1125.0 (2)N9—C24—C23121.6 (2)
C5—C6—N3116.3 (2)N9—C24—H24115.3 (18)
C1—C6—N3118.6 (2)C23—C24—H24123.0 (18)
O8—C7—C12126.8 (2)N10—C25—H25A107.4 (18)
O8—C7—C8122.0 (2)N10—C25—H25B112.7 (17)
C12—C7—C8111.2 (2)H25A—C25—H25B106 (2)
C9—C8—C7126.1 (2)N10—C25—H25C110.4 (18)
C9—C8—N4117.60 (19)H25A—C25—H25C113 (3)
C7—C8—N4116.3 (2)H25B—C25—H25C108 (2)
C8—C9—C10117.8 (2)N10—C26—H26A109.2 (19)
C8—C9—H9119.3 (14)N10—C26—H26B107.2 (18)
C10—C9—H9122.8 (14)H26A—C26—H26B110 (3)
C11—C10—C9121.5 (2)N10—C26—H26C113.3 (18)
C11—C10—N5118.9 (2)H26A—C26—H26C111 (3)
C9—C10—N5119.65 (19)H26B—C26—H26C105 (2)
O1—C1—C2—C3173.6 (2)O12—N5—C10—C115.6 (3)
C6—C1—C2—C33.0 (3)O11—N5—C10—C11174.2 (2)
O1—C1—C2—N15.7 (4)O12—N5—C10—C9175.0 (2)
C6—C1—C2—N1177.75 (19)O11—N5—C10—C95.2 (3)
O2—N1—C2—C3163.2 (2)C9—C10—C11—C122.1 (3)
O3—N1—C2—C316.1 (3)N5—C10—C11—C12178.57 (19)
O2—N1—C2—C117.4 (3)C10—C11—C12—C71.3 (3)
O3—N1—C2—C1163.2 (2)C10—C11—C12—N6178.93 (19)
C1—C2—C3—C40.6 (4)O8—C7—C12—C11179.0 (2)
N1—C2—C3—C4179.9 (2)C8—C7—C12—C111.4 (3)
C2—C3—C4—C51.0 (3)O8—C7—C12—N61.2 (4)
C2—C3—C4—N2178.8 (2)C8—C7—C12—N6178.40 (19)
O4—N2—C4—C5175.9 (2)O13—N6—C12—C1127.1 (3)
O5—N2—C4—C54.6 (3)O14—N6—C12—C11152.0 (2)
O4—N2—C4—C36.2 (3)O13—N6—C12—C7152.7 (2)
O5—N2—C4—C3173.3 (2)O14—N6—C12—C728.3 (3)
C3—C4—C5—C60.2 (3)C17—N7—C13—C140.9 (4)
N2—C4—C5—C6177.6 (2)N7—C13—C14—C151.2 (4)
C4—C5—C6—C13.1 (4)C18—N8—C15—C16173.7 (2)
C4—C5—C6—N3177.3 (2)C19—N8—C15—C161.6 (3)
O1—C1—C6—C5172.4 (2)C18—N8—C15—C146.1 (4)
C2—C1—C6—C54.2 (3)C19—N8—C15—C14178.3 (2)
O1—C1—C6—N37.2 (3)C13—C14—C15—N8179.3 (2)
C2—C1—C6—N3176.10 (19)C13—C14—C15—C160.8 (3)
O7—N3—C6—C5148.0 (2)N8—C15—C16—C17179.8 (2)
O6—N3—C6—C530.4 (3)C14—C15—C16—C170.3 (3)
O7—N3—C6—C132.3 (3)C13—N7—C17—C160.4 (4)
O6—N3—C6—C1149.2 (2)C15—C16—C17—N70.1 (4)
O8—C7—C8—C9176.6 (2)C24—N9—C20—C211.3 (4)
C12—C7—C8—C93.7 (3)N9—C20—C21—C220.5 (4)
O8—C7—C8—N41.9 (3)C25—N10—C22—C23178.1 (2)
C12—C7—C8—N4177.74 (19)C26—N10—C22—C231.6 (3)
O9—N4—C8—C9125.8 (2)C25—N10—C22—C212.1 (3)
O10—N4—C8—C954.2 (3)C26—N10—C22—C21178.2 (2)
O9—N4—C8—C755.5 (3)C20—C21—C22—N10179.6 (2)
O10—N4—C8—C7124.5 (2)C20—C21—C22—C230.6 (3)
C7—C8—C9—C103.2 (3)N10—C22—C23—C24179.3 (2)
N4—C8—C9—C10178.3 (2)C21—C22—C23—C240.9 (3)
C8—C9—C10—C110.1 (3)C20—N9—C24—C231.0 (4)
C8—C9—C10—N5179.3 (2)C22—C23—C24—N90.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H···O10.86 (3)1.83 (3)2.640 (3)156 (3)
N7—H···O20.86 (3)2.41 (3)2.986 (3)125 (2)
N9—H···O80.89 (3)1.84 (3)2.669 (3)154 (2)
N9—H···O140.89 (3)2.34 (3)2.934 (3)124 (2)
C3—H3···O30.93 (3)2.38 (3)2.661 (3)97 (2)
C3—H3···O40.93 (3)2.42 (3)2.718 (3)99 (2)
C5—H5···O50.95 (3)2.45 (3)2.696 (3)94.2 (17)
C5—H5···O60.95 (3)2.37 (3)2.701 (3)99.6 (18)
C5—H5···O100.95 (3)2.72 (3)3.237 (3)114.6 (19)
C9—H9···O100.96 (2)2.68 (2)2.860 (3)91.0 (15)
C9—H9···O110.96 (2)2.47 (2)2.712 (3)94.1 (15)
C11—H11···O120.94 (3)2.40 (3)2.702 (3)98.2 (18)
C11—H11···O130.94 (3)2.41 (3)2.681 (3)96.0 (18)
C13—H13···O10.95 (3)2.87 (3)3.201 (3)102 (2)
C17—H17···O20.93 (3)2.51 (3)3.090 (3)121 (2)
C20—H20···O80.94 (3)2.94 (3)3.232 (3)99.2 (17)
C24—H24···O140.92 (3)2.40 (3)3.007 (3)123 (2)
C11—H11···O4i0.94 (3)2.56 (3)3.430 (3)153 (2)
C11—H11···O12i0.94 (3)2.66 (3)3.195 (3)116.7 (19)
C9—H9···O2ii0.96 (2)2.56 (2)3.501 (3)169.5 (19)
C9—H9···O3ii0.96 (2)2.89 (2)3.552 (3)127.7 (17)
C14—H14···O10iii0.92 (3)2.32 (3)3.186 (3)156 (2)
C21—H21···O6iii0.93 (3)2.45 (3)3.328 (3)159 (3)
C13—H13···O5iii0.95 (3)2.86 (3)3.733 (3)153 (2)
C25—H25C···O6iii1.03 (3)2.94 (3)3.579 (3)121 (2)
C17—H17···O5iv0.93 (3)2.78 (3)3.140 (3)104.3 (19)
C23—H23···O11iv0.95 (2)2.58 (2)3.163 (3)119.7 (18)
C17—H17···O11iv0.93 (3)2.45 (3)3.156 (3)133 (2)
C16—H16···O5iv0.93 (2)2.68 (3)3.098 (3)107.9 (18)
C19—H19B···O13v0.93 (3)2.48 (3)3.188 (3)133 (3)
C16—H16···O13v0.93 (2)2.94 (3)3.784 (3)151 (2)
C26—H26C···O13v0.95 (3)2.77 (3)3.524 (3)137 (2)
C26—H26C···O14v0.95 (3)2.98 (3)3.245 (3)97 (2)
C19—H19A···O7vi0.85 (4)2.42 (4)3.273 (3)177 (3)
C26—H26B···O9vi0.94 (3)2.46 (3)3.398 (3)176 (2)
C18—H18A···O7vi0.95 (4)2.84 (4)3.695 (4)151 (3)
C25—H25A···O9vi0.96 (3)2.85 (3)3.706 (3)149 (2)
C18—H18C···O3vii0.98 (3)2.95 (3)3.857 (4)153 (2)
C25—H25B···O12viii0.97 (3)2.74 (3)3.406 (3)126 (2)
C24—H24···O9viii0.92 (3)2.88 (3)3.380 (3)116 (2)
C26—H26A···O11viii0.95 (3)2.76 (3)3.363 (3)122 (2)
C25—H25A···O3ix0.96 (3)2.87 (3)3.651 (3)139 (2)
C25—H25B···O4ix0.97 (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, y1/2, z+1/2; (iv) x, y+3/2, z1/2; (v) x, y1/2, z1/2; (vi) x, y+1/2, z1/2; (vii) x+1, y+1, z; (viii) x, y+1, z; (ix) x, y1, z.

Experimental details

Crystal data
Chemical formulaC7H11N2·C6H2N3O7
Mr351.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)15.274 (4), 12.617 (3), 19.795 (4)
β (°) 129.996 (13)
V3)2922.4 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.50 × 0.40 × 0.20
Data collection
DiffractometerCCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.937, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
24887, 6947, 5744
Rint0.069
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.155, 1.20
No. of reflections6947
No. of parameters555
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.50, 0.32

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

Selected geometric parameters (Å, º) top
O1—C11.235 (3)N2—C41.441 (3)
O2—N11.224 (3)N3—C61.454 (3)
O3—N11.226 (3)N4—C81.457 (3)
O4—N21.223 (3)N5—C101.444 (3)
O5—N21.232 (3)N6—C121.451 (3)
O6—N31.230 (3)N7—C171.340 (3)
O7—N31.215 (3)N7—C131.345 (3)
O8—C71.240 (3)N8—C151.337 (3)
O9—N41.218 (3)N8—C181.448 (3)
O10—N41.218 (3)N8—C191.458 (3)
O11—N51.228 (2)N9—C241.337 (3)
O12—N51.225 (3)N9—C201.344 (3)
O13—N61.221 (3)N10—C221.335 (3)
O14—N61.225 (3)N10—C251.458 (3)
N1—C21.454 (3)N10—C261.463 (3)
O2—N1—O3122.4 (2)O12—N5—C10118.45 (18)
O2—N1—C2119.45 (19)O11—N5—C10117.91 (19)
O3—N1—C2118.2 (2)O13—N6—O14123.37 (19)
O4—N2—O5123.5 (2)O13—N6—C12117.95 (19)
O4—N2—C4118.7 (2)O14—N6—C12118.67 (19)
O5—N2—C4117.8 (2)C17—N7—C13119.9 (2)
O7—N3—O6123.1 (2)C15—N8—C18122.6 (2)
O7—N3—C6119.1 (2)C15—N8—C19120.7 (2)
O6—N3—C6117.8 (2)C18—N8—C19116.3 (2)
O9—N4—O10123.4 (2)C24—N9—C20120.3 (2)
O9—N4—C8118.23 (19)C22—N10—C25120.8 (2)
O10—N4—C8118.3 (2)C22—N10—C26120.3 (2)
O12—N5—O11123.6 (2)C25—N10—C26118.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H'···O10.86 (3)1.83 (3)2.640 (3)156 (3)
N7—H'···O20.86 (3)2.41 (3)2.986 (3)125 (2)
N9—H''···O80.89 (3)1.84 (3)2.669 (3)154 (2)
N9—H''···O140.89 (3)2.34 (3)2.934 (3)124 (2)
C3—H3···O30.93 (3)2.38 (3)2.661 (3)97 (2)
C3—H3···O40.93 (3)2.42 (3)2.718 (3)99 (2)
C5—H5···O50.95 (3)2.45 (3)2.696 (3)94.2 (17)
C5—H5···O60.95 (3)2.37 (3)2.701 (3)99.6 (18)
C5—H5···O100.95 (3)2.72 (3)3.237 (3)114.6 (19)
C9—H9···O100.96 (2)2.68 (2)2.860 (3)91.0 (15)
C9—H9···O110.96 (2)2.47 (2)2.712 (3)94.1 (15)
C11—H11···O120.94 (3)2.40 (3)2.702 (3)98.2 (18)
C11—H11···O130.94 (3)2.41 (3)2.681 (3)96.0 (18)
C13—H13···O10.95 (3)2.87 (3)3.201 (3)102 (2)
C17—H17···O20.93 (3)2.51 (3)3.090 (3)121 (2)
C20—H20···O80.94 (3)2.94 (3)3.232 (3)99.2 (17)
C24—H24···O140.92 (3)2.40 (3)3.007 (3)123 (2)
C11—H11···O4i0.94 (3)2.56 (3)3.430 (3)153 (2)
C11—H11···O12i0.94 (3)2.66 (3)3.195 (3)116.7 (19)
C9—H9···O2ii0.96 (2)2.56 (2)3.501 (3)169.5 (19)
C9—H9···O3ii0.96 (2)2.89 (2)3.552 (3)127.7 (17)
C14—H14···O10iii0.92 (3)2.32 (3)3.186 (3)156 (2)
C21—H21···O6iii0.93 (3)2.45 (3)3.328 (3)159 (3)
C13—H13···O5iii0.95 (3)2.86 (3)3.733 (3)153 (2)
C25—H25C···O6iii1.03 (3)2.94 (3)3.579 (3)121 (2)
C17—H17···O5iv0.93 (3)2.78 (3)3.140 (3)104.3 (19)
C23—H23···O11iv0.95 (2)2.58 (2)3.163 (3)119.7 (18)
C17—H17···O11iv0.93 (3)2.45 (3)3.156 (3)133 (2)
C16—H16···O5iv0.93 (2)2.68 (3)3.098 (3)107.9 (18)
C19—H19B···O13v0.93 (3)2.48 (3)3.188 (3)133 (3)
C16—H16···O13v0.93 (2)2.94 (3)3.784 (3)151 (2)
C26—H26C···O13v0.95 (3)2.77 (3)3.524 (3)137 (2)
C26—H26C···O14v0.95 (3)2.98 (3)3.245 (3)97 (2)
C19—H19A···O7vi0.85 (4)2.42 (4)3.273 (3)177 (3)
C26—H26B···O9vi0.94 (3)2.46 (3)3.398 (3)176 (2)
C18—H18A···O7vi0.95 (4)2.84 (4)3.695 (4)151 (3)
C25—H25A···O9vi0.96 (3)2.85 (3)3.706 (3)149 (2)
C18—H18C···O3vii0.98 (3)2.95 (3)3.857 (4)153 (2)
C25—H25B···O12viii0.97 (3)2.74 (3)3.406 (3)126 (2)
C24—H24···O9viii0.92 (3)2.88 (3)3.380 (3)116 (2)
C26—H26A···O11viii0.95 (3)2.76 (3)3.363 (3)122 (2)
C25—H25A···O3ix0.96 (3)2.87 (3)3.651 (3)139 (2)
C25—H25B···O4ix0.97 (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, y1/2, z+1/2; (iv) x, y+3/2, z1/2; (v) x, y1/2, z1/2; (vi) x, y+1/2, z1/2; (vii) x+1, y+1, z; (viii) x, y+1, z; (ix) x, y1, z.
 

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