organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

3,5-Di­methyl­pyrazolium 3,5-di­nitro­salicylate

aTianmu College of ZheJiang A & F University, Lin'An 311300, People's Republic of China
*Correspondence e-mail: shouwenjin@yahoo.cn

(Received 10 September 2012; accepted 6 October 2012; online 13 October 2012)

In the title mol­ecular salt, C5H9N2+·C7H3N2O7, the roughly planar anion (r.m.s. deviation = 0.120 Å) has been deprotonated at the phenol group. An intra­molecular 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 inter­actions consolidate the packing.

Related literature

For a related structure and background to hydrogen-bonding inter­actions, see: Jin et al. (2010[Jin, S. W., Zhang, W. B., Liu, L., Gao, H. F., Wang, D. Q., Chen, R. P. & Xu, X. L. (2010). J. Mol. Struct. 975, 128-136.]). For another related structure, see: Smith et al. (2011[Smith, G., Wermuth, U. D., Healy, P. C. & White, J. M. (2011). J. Chem. Crystallogr. 41, 1649-1662.]).

[Scheme 1]

Experimental

Crystal data
  • C5H9N2+·C7H3N2O7

  • Mr = 324.26

  • Monoclinic, P 21

  • 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[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.959, Tmax = 0.986

  • 3523 measured reflections

  • 2301 independent reflections

  • 1659 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) [-x, y-{\script{3\over 2}}, -z+1]; (iii) [-x+1, y+{\script{1\over 2}}, -z+2].

Data collection: SMART (Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Organic acid-base adducts based on hydrogen bonding are a research field receiving great attention in recent years. As an extension of our study concentrating on hydrogen bonded assembly of organic acid and organic base (Jin et al., 2010), herein we report the crystal structure of 3,5-dimethylpyrazolium 3,5-dinitrosalicylate.

The crystal of the title compound of the formula C12H12N4O7 was obtained by recrystallization of the mixture of 3,5-dimethylpyrazole and 3,5-dinitrosalicylic acid acid from the MeOH solution.

In this case (Fig. 1) it is the phenol H that has been deprotonated. The C—O distance 1.284 (4) Å concerning the phenolate is similar to the proton transfer compound bearing the 3,5-dinitrosalicylate in which only the phenol group has been deprotonated (Smith et al., 2011). The C—O distances O(2)—C(6), 1.300 (4) Å, O(3)—C(6), 1.223 (4) Å; in the COOH show characteristic C—O, and C=O distances which are also confirming the reliability of adding H atoms experimentally by different electron density onto O atoms.

One anion is bonded to one cation via N—H···O, and CH3—O associations to form a heteroadduct.

For the presence of these interactions, there are close joint motifs with descriptors of R21(6), and R12(6). The usual intramolecular hydrogen bond is found between the phenolate and the carboxyl group to exhibit a S11(6) graph. The heteroadducts were linked together by the CH3—O association between the methyl group of the pyrazole and the 5-nitro group with C—O distance of 3.415 Å to form one-dimensional chain running along the direction that made an angle of ca 60° with the a axis (Fig. 2). The chains were further stacked along the direction that is perpendicular with its extending direction via the interchain N-π interaction between the 5-nitro group and the phenyl ring of the anion with N—Cg distance of 3.236 Å to form two-dimensional sheet extending parallel to the ab plane. The sheets were further stacked along the c axis direction by the CH—O, N—H···O, and O—H···O associations to form three-dimensional ABAB layer network structure. Herein the chains at adjacent layers intersect at an angle of ca 120° with each other.

Related literature top

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

Experimental top

A solution of 3,5-dimethyl pyrazole (19.2 mg, 0.2 mmol) in 5 ml of MeOH was added to a MeOH solution (6 ml) containing 3,5-dinitrosalicylic acid (22.8 mg, 0.1 mmol) under continuous stirring. The solution was stirred for about 1 h at room temperature, then the solution was filtered into a test tube. The solution was left standing at room temperature for several days, yellow blocks were isolated after slow evaporation of the solution in air at ambient temperature. The crystals were collected and dried in air to give the title compound.

Refinement top

The absolute structure could not be determined in the present refinement. Hydrogen atoms attached to the C atoms were placed in calculated positions with d(C—H) = 0.93–0.96 Å. Positions of the hydrogen atoms at the NH, and COOH groups were located from the Fourier difference syntheses and refined independently. All Uiso values were restrained on Ueq values of the parent atoms.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The one-dimensional chain formed through the CH3—O interaction.
3,5-Dimethylpyrazolium 3,5-dinitrosalicylate top
Crystal data top
C5H9N2+·C7H3N2O7F(000) = 336
Mr = 324.26Dx = 1.547 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.1183 (7) ÅCell parameters from 1025 reflections
b = 6.0636 (5) Åθ = 2.5–22.6°
c = 14.1453 (11) ŵ = 0.13 mm1
β = 91.904 (1)°T = 293 K
V = 695.93 (10) Å3Block, colorless
Z = 20.40 × 0.27 × 0.11 mm
Data collection top
Bruker SMART CCD
diffractometer
2301 independent reflections
Radiation source: fine-focus sealed tube1659 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 99
Tmin = 0.959, Tmax = 0.986k = 77
3523 measured reflectionsl = 1612
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-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 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = 0.18 e Å3
Crystal data top
C5H9N2+·C7H3N2O7V = 695.93 (10) Å3
Mr = 324.26Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.1183 (7) ŵ = 0.13 mm1
b = 6.0636 (5) ÅT = 293 K
c = 14.1453 (11) Å0.40 × 0.27 × 0.11 mm
β = 91.904 (1)°
Data collection top
Bruker SMART CCD
diffractometer
2301 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
1659 reflections with I > 2σ(I)
Tmin = 0.959, Tmax = 0.986Rint = 0.040
3523 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0471 restraint
wR(F2) = 0.105H-atom parameters constrained
S = 1.02Δρmax = 0.16 e Å3
2301 reflectionsΔρmin = 0.18 e Å3
208 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
N10.2255 (4)0.7148 (5)0.2340 (2)0.0463 (7)
H10.27260.83810.22180.056*
N20.2198 (3)0.6193 (5)0.31994 (19)0.0469 (8)
H20.26350.67240.37130.056*
C60.3512 (4)0.7229 (6)0.5523 (2)0.0405 (8)
N30.2184 (3)1.3159 (5)0.7707 (2)0.0487 (7)
N40.5550 (4)0.7118 (5)0.8914 (2)0.0484 (8)
O10.5414 (3)0.5277 (4)0.70183 (15)0.0454 (6)
O20.4254 (3)0.5367 (4)0.53738 (15)0.0581 (7)
H2A0.47700.49900.58550.087*
O30.2657 (3)0.8102 (4)0.48999 (14)0.0493 (6)
O40.1417 (3)1.4008 (4)0.70451 (18)0.0632 (7)
O50.2271 (3)1.3968 (5)0.85007 (18)0.0689 (8)
O60.5255 (4)0.7837 (5)0.96945 (17)0.0833 (10)
O70.6547 (4)0.5660 (5)0.87978 (17)0.0698 (8)
C10.1300 (5)0.6449 (8)0.0686 (2)0.0717 (13)
H1A0.17870.78680.05840.108*
H1B0.01550.64920.04950.108*
H1C0.18540.53600.03200.108*
C20.1462 (4)0.5868 (6)0.1713 (2)0.0464 (9)
C30.0892 (4)0.4066 (7)0.2187 (3)0.0544 (10)
H30.02980.28920.19250.065*
C40.1370 (4)0.4321 (6)0.3134 (2)0.0464 (9)
C50.1105 (4)0.2906 (7)0.3972 (3)0.0625 (11)
H5A0.21480.25700.42780.094*
H5B0.05720.15620.37740.094*
H5C0.04220.36720.44060.094*
C120.4688 (4)0.7102 (5)0.7195 (2)0.0353 (8)
C70.3732 (3)0.8231 (6)0.64774 (19)0.0339 (7)
C80.2969 (4)1.0188 (6)0.6644 (2)0.0376 (8)
H80.23961.09050.61540.045*
C90.3041 (4)1.1108 (6)0.7533 (2)0.0368 (8)
C100.3900 (4)1.0088 (6)0.8269 (2)0.0396 (8)
H100.39351.07110.88700.048*
C110.4701 (4)0.8142 (6)0.8101 (2)0.0366 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0503 (17)0.0446 (18)0.0438 (17)0.0035 (14)0.0020 (13)0.0021 (14)
N20.0493 (18)0.051 (2)0.0397 (16)0.0042 (16)0.0060 (13)0.0055 (16)
C60.0382 (18)0.048 (2)0.0356 (19)0.0017 (17)0.0045 (16)0.0016 (17)
N30.0479 (17)0.0412 (19)0.057 (2)0.0007 (16)0.0029 (15)0.0032 (18)
N40.064 (2)0.044 (2)0.0372 (18)0.0012 (16)0.0046 (15)0.0033 (15)
O10.0544 (14)0.0412 (14)0.0404 (13)0.0081 (12)0.0011 (10)0.0056 (11)
O20.0701 (17)0.0628 (18)0.0408 (14)0.0203 (15)0.0077 (11)0.0155 (13)
O30.0554 (13)0.0590 (16)0.0329 (12)0.0050 (13)0.0072 (11)0.0004 (12)
O40.0679 (17)0.0510 (17)0.0699 (17)0.0183 (14)0.0112 (14)0.0030 (15)
O50.088 (2)0.0582 (18)0.0602 (17)0.0083 (16)0.0045 (14)0.0181 (15)
O60.144 (3)0.073 (2)0.0317 (15)0.033 (2)0.0088 (15)0.0034 (14)
O70.088 (2)0.070 (2)0.0509 (15)0.0294 (18)0.0100 (14)0.0072 (15)
C10.079 (3)0.093 (3)0.043 (2)0.017 (3)0.005 (2)0.009 (2)
C20.044 (2)0.052 (3)0.0424 (19)0.0036 (19)0.0059 (16)0.0103 (19)
C30.050 (2)0.056 (3)0.057 (2)0.006 (2)0.0065 (18)0.023 (2)
C40.0363 (19)0.042 (2)0.061 (2)0.0018 (18)0.0040 (16)0.0034 (19)
C50.061 (2)0.057 (3)0.069 (3)0.001 (2)0.0008 (19)0.010 (2)
C120.0346 (18)0.038 (2)0.0338 (18)0.0056 (16)0.0023 (14)0.0013 (16)
C70.0348 (16)0.0367 (19)0.0302 (16)0.0059 (16)0.0012 (13)0.0009 (15)
C80.0393 (19)0.039 (2)0.0346 (18)0.0019 (17)0.0034 (14)0.0036 (16)
C90.0394 (19)0.0310 (19)0.0399 (18)0.0045 (16)0.0016 (14)0.0010 (16)
C100.049 (2)0.040 (2)0.0299 (17)0.0064 (18)0.0020 (15)0.0014 (16)
C110.0403 (18)0.0381 (19)0.0312 (17)0.0023 (18)0.0024 (13)0.0046 (16)
Geometric parameters (Å, º) top
N1—C21.329 (4)C1—H1B0.9600
N1—N21.348 (4)C1—H1C0.9600
N1—H10.8600C2—C31.371 (5)
N2—C41.321 (4)C3—C41.391 (5)
N2—H20.8600C3—H30.9300
C6—O31.224 (4)C4—C51.484 (5)
C6—O21.301 (4)C5—H5A0.9600
C6—C71.486 (4)C5—H5B0.9600
N3—O41.221 (3)C5—H5C0.9600
N3—O51.226 (3)C12—C111.427 (4)
N3—C91.449 (4)C12—C71.431 (4)
N4—O71.213 (4)C7—C81.363 (4)
N4—O61.218 (3)C8—C91.375 (4)
N4—C111.460 (4)C8—H80.9300
O1—C121.283 (4)C9—C101.379 (4)
O2—H2A0.8200C10—C111.372 (4)
C1—C21.496 (5)C10—H100.9300
C1—H1A0.9600
C2—N1—N2108.7 (3)N2—C4—C3106.7 (3)
C2—N1—H1125.6N2—C4—C5121.9 (3)
N2—N1—H1125.6C3—C4—C5131.4 (3)
C4—N2—N1109.8 (3)C4—C5—H5A109.5
C4—N2—H2125.1C4—C5—H5B109.5
N1—N2—H2125.1H5A—C5—H5B109.5
O3—C6—O2120.9 (3)C4—C5—H5C109.5
O3—C6—C7121.7 (3)H5A—C5—H5C109.5
O2—C6—C7117.4 (3)H5B—C5—H5C109.5
O4—N3—O5123.1 (3)O1—C12—C11124.5 (3)
O4—N3—C9117.9 (3)O1—C12—C7121.0 (3)
O5—N3—C9119.0 (3)C11—C12—C7114.4 (3)
O7—N4—O6122.4 (3)C8—C7—C12122.2 (3)
O7—N4—C11120.2 (3)C8—C7—C6118.1 (3)
O6—N4—C11117.4 (3)C12—C7—C6119.7 (3)
C6—O2—H2A109.5C7—C8—C9120.4 (3)
C2—C1—H1A109.5C7—C8—H8119.8
C2—C1—H1B109.5C9—C8—H8119.8
H1A—C1—H1B109.5C8—C9—C10120.8 (3)
C2—C1—H1C109.5C8—C9—N3119.8 (3)
H1A—C1—H1C109.5C10—C9—N3119.4 (3)
H1B—C1—H1C109.5C11—C10—C9119.1 (3)
N1—C2—C3107.6 (3)C11—C10—H10120.5
N1—C2—C1122.4 (4)C9—C10—H10120.5
C3—C2—C1130.0 (3)C10—C11—C12123.1 (3)
C2—C3—C4107.2 (3)C10—C11—N4116.3 (3)
C2—C3—H3126.4C12—C11—N4120.6 (3)
C4—C3—H3126.4
C2—N1—N2—C40.4 (4)C7—C8—C9—C100.8 (5)
N2—N1—C2—C30.0 (4)C7—C8—C9—N3178.3 (3)
N2—N1—C2—C1179.8 (3)O4—N3—C9—C80.0 (4)
N1—C2—C3—C40.3 (4)O5—N3—C9—C8179.4 (3)
C1—C2—C3—C4179.9 (4)O4—N3—C9—C10179.1 (3)
N1—N2—C4—C30.6 (3)O5—N3—C9—C101.5 (4)
N1—N2—C4—C5179.9 (3)C8—C9—C10—C110.6 (5)
C2—C3—C4—N20.6 (4)N3—C9—C10—C11179.7 (3)
C2—C3—C4—C5180.0 (4)C9—C10—C11—C120.2 (4)
O1—C12—C7—C8179.0 (3)C9—C10—C11—N4178.4 (3)
C11—C12—C7—C82.9 (4)O1—C12—C11—C10179.5 (3)
O1—C12—C7—C62.8 (4)C7—C12—C11—C101.4 (4)
C11—C12—C7—C6175.3 (3)O1—C12—C11—N41.3 (5)
O3—C6—C7—C80.9 (4)C7—C12—C11—N4176.7 (3)
O2—C6—C7—C8179.7 (3)O7—N4—C11—C10165.3 (3)
O3—C6—C7—C12177.4 (3)O6—N4—C11—C1012.4 (4)
O2—C6—C7—C122.1 (4)O7—N4—C11—C1216.5 (5)
C12—C7—C8—C92.7 (5)O6—N4—C11—C12165.9 (3)
C6—C7—C8—C9175.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O7i0.862.092.859 (4)148
N1—H1···O1i0.862.162.809 (4)132
N2—H2···O30.861.882.684 (3)156
O2—H2A···O10.821.722.481 (3)154
C1—H1A···O7i0.962.323.166 (5)147
C5—H5B···O4ii0.962.493.414 (5)160
C10—H10···O6iii0.932.483.379 (4)164
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y3/2, z+1; (iii) x+1, y+1/2, z+2.

Experimental details

Crystal data
Chemical formulaC5H9N2+·C7H3N2O7
Mr324.26
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)8.1183 (7), 6.0636 (5), 14.1453 (11)
β (°) 91.904 (1)
V3)695.93 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.40 × 0.27 × 0.11
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.959, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
3523, 2301, 1659
Rint0.040
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.105, 1.02
No. of reflections2301
No. of parameters208
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O7i0.862.092.859 (4)148
N1—H1···O1i0.862.162.809 (4)132
N2—H2···O30.861.882.684 (3)156
O2—H2A···O10.821.722.481 (3)154
C1—H1A···O7i0.962.323.166 (5)147
C5—H5B···O4ii0.962.493.414 (5)160
C10—H10···O6iii0.932.483.379 (4)164
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y3/2, z+1; (iii) x+1, y+1/2, z+2.
 

Acknowledgements

We gratefully acknowledge the financial support of the Education Office Foundation of Zhejiang Province (project No. Y201017321) and the innovation project of Zhejiang A & F University.

References

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