3,5-Dimethyl-pyrazolium 3,5-dinitro-salicylate.

In the title mol-ecular salt, C(5)H(9)N(2) (+)·C(7)H(3)N(2)O(7) (-), the roughly planar anion (r.m.s. deviation = 0.120 Å) has been deprotonated at the phenol group. An intra-molecular O-H⋯O hydrogen bond in the anion generates an S(6) ring. In the crystal, the components are linked by cation-to-anion N-H⋯O and N-H⋯(O,O) hydrogen bonds, generating [010] double chains. Weak C-H⋯O inter-actions consolidate the packing.

Related literature

For a related structure and background to hydrogen-bonding inter­actions, see: Jin et al. (2010 ▶). For another related structure, see: Smith et al. (2011 ▶).

Experimental

Crystal data

C5H9N2 +·C7n class="Species">H3N2O7 −

M = 324.26

Monoclinic,

a = 8.1183 (7) Å

b = 6.0636 (5) Å

c = 14.1453 (11) Å

β = 91.904 (1)°

V = 695.93 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.40 × 0.27 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.959, T max = 0.986

3523 measured reflections

2301 independent reflections

1659 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.105

S = 1.02

2301 reflections

208 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812041906/hb6958sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041906/hb6958Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041906/hb6958Isup3.cml

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

C5H9N2+·C7H3N2O7−	F(000) = 336
Mr = 324.26	Dx = 1.547 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.1183 (7) Å	Cell parameters from 1025 reflections
b = 6.0636 (5) Å	θ = 2.5–22.6°
c = 14.1453 (11) Å	µ = 0.13 mm−1
β = 91.904 (1)°	T = 293 K
V = 695.93 (10) Å3	Block, colorless
Z = 2	0.40 × 0.27 × 0.11 mm

Bruker SMART CCD diffractometer	2301 independent reflections
Radiation source: fine-focus sealed tube	1659 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.959, Tmax = 0.986	k = −7→7
3523 measured reflections	l = −16→12

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0405P)2] where P = (Fo2 + 2Fc2)/3
2301 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.18 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
N1	0.2255 (4)	0.7148 (5)	0.2340 (2)	0.0463 (7)
H1	0.2726	0.8381	0.2218	0.056*
N2	0.2198 (3)	0.6193 (5)	0.31994 (19)	0.0469 (8)
H2	0.2635	0.6724	0.3713	0.056*
C6	0.3512 (4)	0.7229 (6)	0.5523 (2)	0.0405 (8)
N3	0.2184 (3)	1.3159 (5)	0.7707 (2)	0.0487 (7)
N4	0.5550 (4)	0.7118 (5)	0.8914 (2)	0.0484 (8)
O1	0.5414 (3)	0.5277 (4)	0.70183 (15)	0.0454 (6)
O2	0.4254 (3)	0.5367 (4)	0.53738 (15)	0.0581 (7)
H2A	0.4770	0.4990	0.5855	0.087*
O3	0.2657 (3)	0.8102 (4)	0.48999 (14)	0.0493 (6)
O4	0.1417 (3)	1.4008 (4)	0.70451 (18)	0.0632 (7)
O5	0.2271 (3)	1.3968 (5)	0.85007 (18)	0.0689 (8)
O6	0.5255 (4)	0.7837 (5)	0.96945 (17)	0.0833 (10)
O7	0.6547 (4)	0.5660 (5)	0.87978 (17)	0.0698 (8)
C1	0.1300 (5)	0.6449 (8)	0.0686 (2)	0.0717 (13)
H1A	0.1787	0.7868	0.0584	0.108*
H1B	0.0155	0.6492	0.0495	0.108*
H1C	0.1854	0.5360	0.0320	0.108*
C2	0.1462 (4)	0.5868 (6)	0.1713 (2)	0.0464 (9)
C3	0.0892 (4)	0.4066 (7)	0.2187 (3)	0.0544 (10)
H3	0.0298	0.2892	0.1925	0.065*
C4	0.1370 (4)	0.4321 (6)	0.3134 (2)	0.0464 (9)
C5	0.1105 (4)	0.2906 (7)	0.3972 (3)	0.0625 (11)
H5A	0.2148	0.2570	0.4278	0.094*
H5B	0.0572	0.1562	0.3774	0.094*
H5C	0.0422	0.3672	0.4406	0.094*
C12	0.4688 (4)	0.7102 (5)	0.7195 (2)	0.0353 (8)
C7	0.3732 (3)	0.8231 (6)	0.64774 (19)	0.0339 (7)
C8	0.2969 (4)	1.0188 (6)	0.6644 (2)	0.0376 (8)
H8	0.2396	1.0905	0.6154	0.045*
C9	0.3041 (4)	1.1108 (6)	0.7533 (2)	0.0368 (8)
C10	0.3900 (4)	1.0088 (6)	0.8269 (2)	0.0396 (8)
H10	0.3935	1.0711	0.8870	0.048*
C11	0.4701 (4)	0.8142 (6)	0.8101 (2)	0.0366 (7)

	U11	U22	U33	U12	U13	U23
N1	0.0503 (17)	0.0446 (18)	0.0438 (17)	−0.0035 (14)	−0.0020 (13)	−0.0021 (14)
N2	0.0493 (18)	0.051 (2)	0.0397 (16)	−0.0042 (16)	−0.0060 (13)	−0.0055 (16)
C6	0.0382 (18)	0.048 (2)	0.0356 (19)	−0.0017 (17)	0.0045 (16)	−0.0016 (17)
N3	0.0479 (17)	0.0412 (19)	0.057 (2)	0.0007 (16)	0.0029 (15)	−0.0032 (18)
N4	0.064 (2)	0.044 (2)	0.0372 (18)	−0.0012 (16)	−0.0046 (15)	0.0033 (15)
O1	0.0544 (14)	0.0412 (14)	0.0404 (13)	0.0081 (12)	−0.0011 (10)	−0.0056 (11)
O2	0.0701 (17)	0.0628 (18)	0.0408 (14)	0.0203 (15)	−0.0077 (11)	−0.0155 (13)
O3	0.0554 (13)	0.0590 (16)	0.0329 (12)	0.0050 (13)	−0.0072 (11)	0.0004 (12)
O4	0.0679 (17)	0.0510 (17)	0.0699 (17)	0.0183 (14)	−0.0112 (14)	0.0030 (15)
O5	0.088 (2)	0.0582 (18)	0.0602 (17)	0.0083 (16)	0.0045 (14)	−0.0181 (15)
O6	0.144 (3)	0.073 (2)	0.0317 (15)	0.033 (2)	−0.0088 (15)	−0.0034 (14)
O7	0.088 (2)	0.070 (2)	0.0509 (15)	0.0294 (18)	−0.0100 (14)	0.0072 (15)
C1	0.079 (3)	0.093 (3)	0.043 (2)	−0.017 (3)	−0.005 (2)	−0.009 (2)
C2	0.044 (2)	0.052 (3)	0.0424 (19)	0.0036 (19)	−0.0059 (16)	−0.0103 (19)
C3	0.050 (2)	0.056 (3)	0.057 (2)	−0.006 (2)	−0.0065 (18)	−0.023 (2)
C4	0.0363 (19)	0.042 (2)	0.061 (2)	0.0018 (18)	0.0040 (16)	−0.0034 (19)
C5	0.061 (2)	0.057 (3)	0.069 (3)	−0.001 (2)	−0.0008 (19)	0.010 (2)
C12	0.0346 (18)	0.038 (2)	0.0338 (18)	−0.0056 (16)	0.0023 (14)	0.0013 (16)
C7	0.0348 (16)	0.0367 (19)	0.0302 (16)	−0.0059 (16)	0.0012 (13)	0.0009 (15)
C8	0.0393 (19)	0.039 (2)	0.0346 (18)	−0.0019 (17)	−0.0034 (14)	0.0036 (16)
C9	0.0394 (19)	0.0310 (19)	0.0399 (18)	−0.0045 (16)	0.0016 (14)	−0.0010 (16)
C10	0.049 (2)	0.040 (2)	0.0299 (17)	−0.0064 (18)	0.0020 (15)	−0.0014 (16)
C11	0.0403 (18)	0.0381 (19)	0.0312 (17)	−0.0023 (18)	−0.0024 (13)	0.0046 (16)

N1—C2	1.329 (4)	C1—H1B	0.9600
N1—N2	1.348 (4)	C1—H1C	0.9600
N1—H1	0.8600	C2—C3	1.371 (5)
N2—C4	1.321 (4)	C3—C4	1.391 (5)
N2—H2	0.8600	C3—H3	0.9300
C6—O3	1.224 (4)	C4—C5	1.484 (5)
C6—O2	1.301 (4)	C5—H5A	0.9600
C6—C7	1.486 (4)	C5—H5B	0.9600
N3—O4	1.221 (3)	C5—H5C	0.9600
N3—O5	1.226 (3)	C12—C11	1.427 (4)
N3—C9	1.449 (4)	C12—C7	1.431 (4)
N4—O7	1.213 (4)	C7—C8	1.363 (4)
N4—O6	1.218 (3)	C8—C9	1.375 (4)
N4—C11	1.460 (4)	C8—H8	0.9300
O1—C12	1.283 (4)	C9—C10	1.379 (4)
O2—H2A	0.8200	C10—C11	1.372 (4)
C1—C2	1.496 (5)	C10—H10	0.9300
C1—H1A	0.9600
C2—N1—N2	108.7 (3)	N2—C4—C3	106.7 (3)
C2—N1—H1	125.6	N2—C4—C5	121.9 (3)
N2—N1—H1	125.6	C3—C4—C5	131.4 (3)
C4—N2—N1	109.8 (3)	C4—C5—H5A	109.5
C4—N2—H2	125.1	C4—C5—H5B	109.5
N1—N2—H2	125.1	H5A—C5—H5B	109.5
O3—C6—O2	120.9 (3)	C4—C5—H5C	109.5
O3—C6—C7	121.7 (3)	H5A—C5—H5C	109.5
O2—C6—C7	117.4 (3)	H5B—C5—H5C	109.5
O4—N3—O5	123.1 (3)	O1—C12—C11	124.5 (3)
O4—N3—C9	117.9 (3)	O1—C12—C7	121.0 (3)
O5—N3—C9	119.0 (3)	C11—C12—C7	114.4 (3)
O7—N4—O6	122.4 (3)	C8—C7—C12	122.2 (3)
O7—N4—C11	120.2 (3)	C8—C7—C6	118.1 (3)
O6—N4—C11	117.4 (3)	C12—C7—C6	119.7 (3)
C6—O2—H2A	109.5	C7—C8—C9	120.4 (3)
C2—C1—H1A	109.5	C7—C8—H8	119.8
C2—C1—H1B	109.5	C9—C8—H8	119.8
H1A—C1—H1B	109.5	C8—C9—C10	120.8 (3)
C2—C1—H1C	109.5	C8—C9—N3	119.8 (3)
H1A—C1—H1C	109.5	C10—C9—N3	119.4 (3)
H1B—C1—H1C	109.5	C11—C10—C9	119.1 (3)
N1—C2—C3	107.6 (3)	C11—C10—H10	120.5
N1—C2—C1	122.4 (4)	C9—C10—H10	120.5
C3—C2—C1	130.0 (3)	C10—C11—C12	123.1 (3)
C2—C3—C4	107.2 (3)	C10—C11—N4	116.3 (3)
C2—C3—H3	126.4	C12—C11—N4	120.6 (3)
C4—C3—H3	126.4
C2—N1—N2—C4	−0.4 (4)	C7—C8—C9—C10	0.8 (5)
N2—N1—C2—C3	0.0 (4)	C7—C8—C9—N3	−178.3 (3)
N2—N1—C2—C1	−179.8 (3)	O4—N3—C9—C8	0.0 (4)
N1—C2—C3—C4	0.3 (4)	O5—N3—C9—C8	−179.4 (3)
C1—C2—C3—C4	−179.9 (4)	O4—N3—C9—C10	−179.1 (3)
N1—N2—C4—C3	0.6 (3)	O5—N3—C9—C10	1.5 (4)
N1—N2—C4—C5	−179.9 (3)	C8—C9—C10—C11	0.6 (5)
C2—C3—C4—N2	−0.6 (4)	N3—C9—C10—C11	179.7 (3)
C2—C3—C4—C5	180.0 (4)	C9—C10—C11—C12	−0.2 (4)
O1—C12—C7—C8	−179.0 (3)	C9—C10—C11—N4	−178.4 (3)
C11—C12—C7—C8	2.9 (4)	O1—C12—C11—C10	−179.5 (3)
O1—C12—C7—C6	2.8 (4)	C7—C12—C11—C10	−1.4 (4)
C11—C12—C7—C6	−175.3 (3)	O1—C12—C11—N4	−1.3 (5)
O3—C6—C7—C8	−0.9 (4)	C7—C12—C11—N4	176.7 (3)
O2—C6—C7—C8	179.7 (3)	O7—N4—C11—C10	−165.3 (3)
O3—C6—C7—C12	177.4 (3)	O6—N4—C11—C10	12.4 (4)
O2—C6—C7—C12	−2.1 (4)	O7—N4—C11—C12	16.5 (5)
C12—C7—C8—C9	−2.7 (5)	O6—N4—C11—C12	−165.9 (3)
C6—C7—C8—C9	175.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O7i	0.86	2.09	2.859 (4)	148
N1—H1···O1i	0.86	2.16	2.809 (4)	132
N2—H2···O3	0.86	1.88	2.684 (3)	156
O2—H2A···O1	0.82	1.72	2.481 (3)	154
C1—H1A···O7i	0.96	2.32	3.166 (5)	147
C5—H5B···O4ii	0.96	2.49	3.414 (5)	160
C10—H10···O6iii	0.93	2.48	3.379 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O7i	0.86	2.09	2.859 (4)	148
N1—H1⋯O1i	0.86	2.16	2.809 (4)	132
N2—H2⋯O3	0.86	1.88	2.684 (3)	156
O2—H2A⋯O1	0.82	1.72	2.481 (3)	154
C1—H1A⋯O7i	0.96	2.32	3.166 (5)	147
C5—H5B⋯O4ii	0.96	2.49	3.414 (5)	160
C10—H10⋯O6iii	0.93	2.48	3.379 (4)	164

Symmetry codes: (i) ; (ii) ; (iii) .