Benzotriazolium picrate.

In the crystal structure of the title compound, C(6)H(6)N(3) (+)·C(6)H(2)N(3)O(7) (-), anions and cations are linked into chains along [010] by inter-molecular N-H⋯O hydrogen bonds. These chains are further stabilized by weak C-H⋯O hydrogen bonds and π-π stacking inter-actions with a centroid-centroid distance of 3.908 (1) Å.

Related literature

For applications of imidazolium-based picrate salts, see: Sikder & Sikder (2004 ▶). For related structures, see: Jin et al. (2008 ▶); Hashizume et al. (2001 ▶); Li (2007 ▶); Moreno-Fuquen et al. (2011 ▶); Pi et al. (2009 ▶).

Experimental

Crystal data

C6H6N3 +·C6H2N3O7 −

M = 348.24

Monoclinic,

a = 14.4113 (15) Å

b = 3.7608 (4) Å

c = 24.941 (3) Å

β = 90.598 (2)°

V = 1351.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 298 K

0.35 × 0.08 × 0.06 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.941, T max = 0.991

10116 measured reflections

2793 independent reflections

1772 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.160

S = 1.04

2793 reflections

232 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018307/lh5251sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018307/lh5251Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018307/lh5251Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H6N3+·C6H2N3O7−	F(000) = 712
Mr = 348.24	Dx = 1.711 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1240 reflections
a = 14.4113 (15) Å	θ = 2.8–20.3°
b = 3.7608 (4) Å	µ = 0.14 mm−1
c = 24.941 (3) Å	T = 298 K
β = 90.598 (2)°	Needle, yellow
V = 1351.7 (2) Å3	0.35 × 0.08 × 0.06 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2793 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1772 reflections with I > 2σ(I)
graphite	Rint = 0.068
0.3° wide ω scans	θmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −18→18
Tmin = 0.941, Tmax = 0.991	k = −4→4
10116 measured reflections	l = −28→31

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/3
2793 reflections	(Δ/σ)max < 0.001
232 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.99963 (18)	0.3370 (8)	0.66441 (12)	0.0292 (7)
C2	1.01146 (18)	0.4733 (8)	0.61071 (11)	0.0306 (7)
C3	1.09520 (19)	0.5092 (8)	0.58563 (12)	0.0339 (7)
H3	1.0979	0.6016	0.5511	0.041*
C4	1.17487 (18)	0.4073 (8)	0.61202 (12)	0.0329 (7)
C5	1.17278 (19)	0.2734 (8)	0.66338 (11)	0.0318 (7)
H5	1.2273	0.2056	0.6809	0.038*
C6	1.08877 (19)	0.2420 (8)	0.68823 (11)	0.0298 (7)
N1	0.93044 (16)	0.5892 (7)	0.57961 (10)	0.0359 (6)
N2	1.26389 (18)	0.4342 (8)	0.58494 (12)	0.0447 (7)
N3	1.09156 (17)	0.1027 (7)	0.74265 (10)	0.0365 (6)
C7	0.82043 (17)	0.5020 (7)	0.87509 (12)	0.0282 (7)
C8	0.8186 (2)	0.4915 (8)	0.93112 (12)	0.0377 (8)
H8	0.7672	0.5650	0.9504	0.045*
C9	0.8973 (2)	0.3662 (9)	0.95568 (12)	0.0412 (8)
H9	0.8997	0.3555	0.9929	0.049*
C10	0.9752 (2)	0.2525 (9)	0.92626 (13)	0.0408 (8)
H10	1.0272	0.1713	0.9449	0.049*
C11	0.97677 (19)	0.2573 (8)	0.87192 (12)	0.0365 (8)
H11	1.0281	0.1809	0.8528	0.044*
C12	0.89671 (18)	0.3838 (8)	0.84644 (11)	0.0291 (7)
N4	0.75692 (16)	0.6019 (7)	0.83701 (10)	0.0347 (6)
H4	0.702 (2)	0.678 (9)	0.8423 (12)	0.042*
N5	0.78784 (16)	0.5608 (7)	0.78832 (10)	0.0388 (7)
N6	0.87157 (16)	0.4287 (7)	0.79375 (10)	0.0354 (6)
H6	0.896 (2)	0.343 (8)	0.7615 (13)	0.043*
O1	0.92425 (12)	0.3151 (6)	0.68863 (8)	0.0385 (6)
O2	0.85380 (14)	0.4837 (7)	0.59216 (10)	0.0604 (8)
O3	0.94256 (15)	0.7832 (7)	0.54123 (10)	0.0577 (7)
O4	1.26640 (16)	0.6034 (8)	0.54315 (11)	0.0691 (8)
O5	1.33151 (15)	0.2909 (8)	0.60522 (10)	0.0625 (8)
O6	1.02722 (16)	−0.0819 (6)	0.75823 (9)	0.0497 (6)
O7	1.15869 (17)	0.1753 (8)	0.77088 (10)	0.0642 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0274 (14)	0.0287 (17)	0.0316 (17)	−0.0046 (12)	0.0038 (12)	−0.0064 (13)
C2	0.0299 (15)	0.0319 (17)	0.0301 (17)	−0.0041 (12)	0.0013 (12)	−0.0065 (13)
C3	0.0373 (16)	0.0361 (18)	0.0284 (17)	−0.0073 (14)	0.0062 (13)	−0.0048 (14)
C4	0.0278 (15)	0.0390 (18)	0.0320 (17)	−0.0041 (13)	0.0066 (12)	−0.0071 (14)
C5	0.0276 (15)	0.0345 (17)	0.0332 (18)	0.0027 (12)	−0.0003 (13)	−0.0070 (14)
C6	0.0340 (15)	0.0298 (17)	0.0255 (16)	−0.0003 (13)	0.0021 (13)	−0.0001 (13)
N1	0.0351 (14)	0.0390 (16)	0.0337 (16)	0.0006 (12)	−0.0004 (12)	0.0026 (13)
N2	0.0349 (15)	0.060 (2)	0.0397 (17)	−0.0089 (14)	0.0123 (13)	−0.0074 (15)
N3	0.0382 (14)	0.0397 (16)	0.0317 (15)	0.0063 (12)	0.0051 (12)	0.0005 (12)
C7	0.0265 (14)	0.0245 (16)	0.0337 (17)	−0.0041 (12)	−0.0012 (12)	−0.0025 (13)
C8	0.0354 (16)	0.044 (2)	0.0342 (19)	−0.0017 (14)	0.0082 (14)	−0.0057 (15)
C9	0.0470 (19)	0.049 (2)	0.0280 (18)	−0.0047 (16)	−0.0039 (14)	0.0009 (15)
C10	0.0352 (16)	0.047 (2)	0.040 (2)	0.0036 (14)	−0.0094 (14)	0.0000 (16)
C11	0.0284 (15)	0.0410 (19)	0.040 (2)	0.0030 (13)	0.0030 (13)	−0.0049 (15)
C12	0.0281 (14)	0.0314 (17)	0.0277 (17)	−0.0056 (12)	0.0006 (12)	−0.0029 (13)
N4	0.0254 (12)	0.0407 (16)	0.0381 (16)	0.0031 (11)	0.0025 (12)	−0.0029 (12)
N5	0.0349 (14)	0.0464 (17)	0.0349 (16)	0.0059 (12)	−0.0020 (12)	−0.0040 (13)
N6	0.0336 (14)	0.0434 (16)	0.0294 (15)	0.0026 (12)	0.0024 (11)	−0.0062 (12)
O1	0.0259 (11)	0.0570 (15)	0.0328 (12)	−0.0052 (9)	0.0082 (9)	−0.0033 (10)
O2	0.0279 (12)	0.086 (2)	0.0668 (17)	−0.0040 (12)	0.0000 (11)	0.0266 (15)
O3	0.0533 (15)	0.0726 (19)	0.0471 (16)	−0.0052 (13)	−0.0047 (12)	0.0238 (14)
O4	0.0527 (15)	0.100 (2)	0.0548 (17)	−0.0080 (14)	0.0227 (13)	0.0202 (16)
O5	0.0281 (12)	0.093 (2)	0.0662 (18)	0.0041 (12)	0.0069 (12)	−0.0023 (15)
O6	0.0542 (14)	0.0533 (16)	0.0418 (14)	−0.0085 (12)	0.0131 (11)	0.0082 (12)
O7	0.0510 (15)	0.096 (2)	0.0457 (16)	−0.0068 (14)	−0.0160 (12)	0.0166 (14)

C1—O1	1.251 (3)	N3—O6	1.225 (3)
C1—C2	1.446 (4)	C7—N4	1.365 (4)
C1—C6	1.454 (4)	C7—C12	1.390 (4)
C2—C3	1.372 (4)	C7—C8	1.398 (4)
C2—N1	1.461 (4)	C8—C9	1.366 (4)
C3—C4	1.372 (4)	C8—H8	0.9300
C3—H3	0.9300	C9—C10	1.413 (4)
C4—C5	1.377 (4)	C9—H9	0.9300
C4—N2	1.459 (3)	C10—C11	1.356 (4)
C5—C6	1.371 (4)	C10—H10	0.9300
C5—H5	0.9300	C11—C12	1.395 (4)
C6—N3	1.455 (4)	C11—H11	0.9300
N1—O2	1.218 (3)	C12—N6	1.370 (4)
N1—O3	1.218 (3)	N4—N5	1.307 (3)
N2—O5	1.219 (3)	N4—H4	0.85 (3)
N2—O4	1.222 (3)	N5—N6	1.311 (3)
N3—O7	1.222 (3)	N6—H6	0.94 (3)
O1—C1—C2	125.6 (3)	N4—C7—C8	133.2 (3)
O1—C1—C6	123.7 (3)	C12—C7—C8	121.8 (3)
C2—C1—C6	110.7 (2)	C9—C8—C7	115.7 (3)
C3—C2—C1	124.8 (3)	C9—C8—H8	122.1
C3—C2—N1	115.5 (3)	C7—C8—H8	122.1
C1—C2—N1	119.7 (2)	C8—C9—C10	122.1 (3)
C2—C3—C4	119.3 (3)	C8—C9—H9	119.0
C2—C3—H3	120.3	C10—C9—H9	119.0
C4—C3—H3	120.3	C11—C10—C9	122.5 (3)
C3—C4—C5	121.5 (3)	C11—C10—H10	118.8
C3—C4—N2	119.6 (3)	C9—C10—H10	118.8
C5—C4—N2	118.9 (3)	C10—C11—C12	115.9 (3)
C6—C5—C4	118.7 (3)	C10—C11—H11	122.0
C6—C5—H5	120.7	C12—C11—H11	122.0
C4—C5—H5	120.7	N6—C12—C7	104.5 (2)
C5—C6—C1	125.1 (3)	N6—C12—C11	133.5 (3)
C5—C6—N3	115.9 (2)	C7—C12—C11	122.0 (3)
C1—C6—N3	119.0 (2)	N5—N4—C7	112.4 (2)
O2—N1—O3	122.4 (3)	N5—N4—H4	121 (2)
O2—N1—C2	119.2 (3)	C7—N4—H4	127 (2)
O3—N1—C2	118.4 (2)	N4—N5—N6	105.7 (2)
O5—N2—O4	123.6 (3)	N5—N6—C12	112.3 (2)
O5—N2—C4	118.7 (3)	N5—N6—O1	102.81 (18)
O4—N2—C4	117.7 (3)	C12—N6—O1	144.73 (19)
O7—N3—O6	122.8 (3)	N5—N6—H6	112.9 (19)
O7—N3—C6	118.1 (3)	C12—N6—H6	133.3 (19)
O6—N3—C6	119.1 (2)	C1—O1—N6	134.01 (19)
N4—C7—C12	105.0 (2)
O1—C1—C2—C3	177.1 (3)	C5—C6—N3—O6	−146.4 (3)
C6—C1—C2—C3	−0.1 (4)	C1—C6—N3—O6	33.7 (4)
O1—C1—C2—N1	−2.0 (4)	N4—C7—C8—C9	178.9 (3)
C6—C1—C2—N1	−179.3 (3)	C12—C7—C8—C9	1.5 (4)
C1—C2—C3—C4	0.7 (5)	C7—C8—C9—C10	−0.4 (5)
N1—C2—C3—C4	179.9 (3)	C8—C9—C10—C11	−0.5 (5)
C2—C3—C4—C5	−0.7 (5)	C9—C10—C11—C12	0.3 (5)
C2—C3—C4—N2	178.1 (3)	N4—C7—C12—N6	0.7 (3)
C3—C4—C5—C6	0.1 (4)	C8—C7—C12—N6	178.7 (3)
N2—C4—C5—C6	−178.7 (3)	N4—C7—C12—C11	−179.8 (3)
C4—C5—C6—C1	0.6 (4)	C8—C7—C12—C11	−1.8 (4)
C4—C5—C6—N3	−179.3 (3)	C10—C11—C12—N6	−179.8 (3)
O1—C1—C6—C5	−177.8 (3)	C10—C11—C12—C7	0.8 (4)
C2—C1—C6—C5	−0.5 (4)	C12—C7—N4—N5	−1.0 (3)
O1—C1—C6—N3	2.0 (4)	C8—C7—N4—N5	−178.6 (3)
C2—C1—C6—N3	179.3 (3)	C7—N4—N5—N6	0.9 (3)
C3—C2—N1—O2	160.8 (3)	N4—N5—N6—C12	−0.4 (3)
C1—C2—N1—O2	−20.0 (4)	N4—N5—N6—O1	176.53 (19)
C3—C2—N1—O3	−17.7 (4)	C7—C12—N6—N5	−0.2 (3)
C1—C2—N1—O3	161.4 (3)	C11—C12—N6—N5	−179.6 (3)
C3—C4—N2—O5	−168.3 (3)	C7—C12—N6—O1	−175.0 (3)
C5—C4—N2—O5	10.5 (4)	C11—C12—N6—O1	5.6 (6)
C3—C4—N2—O4	12.4 (4)	C2—C1—O1—N6	−140.9 (3)
C5—C4—N2—O4	−168.8 (3)	C6—C1—O1—N6	36.0 (4)
C5—C6—N3—O7	33.4 (4)	N5—N6—O1—C1	144.9 (3)
C1—C6—N3—O7	−146.5 (3)	C12—N6—O1—C1	−40.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1i	0.85 (3)	2.04 (3)	2.799 (3)	148 (3)
N4—H4···O2i	0.85 (3)	2.16 (3)	2.791 (3)	131 (3)
N6—H6···O1	0.94 (3)	1.87 (3)	2.770 (3)	160 (3)
N6—H6···O6	0.94 (3)	2.48 (3)	3.090 (3)	123 (2)
C8—H8···O2i	0.93	2.57	3.148 (4)	121
C11—H11···O6	0.93	2.56	3.200 (4)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1i	0.85 (3)	2.04 (3)	2.799 (3)	148 (3)
N4—H4⋯O2i	0.85 (3)	2.16 (3)	2.791 (3)	131 (3)
N6—H6⋯O1	0.94 (3)	1.87 (3)	2.770 (3)	160 (3)
N6—H6⋯O6	0.94 (3)	2.48 (3)	3.090 (3)	123 (2)
C8—H8⋯O2i	0.93	2.57	3.148 (4)	121
C11—H11⋯O6	0.93	2.56	3.200 (4)	127

Symmetry code: (i) .