Potassium 3,5 di­nitro­benzoate

metal-organic papers

m496

7H3N2O6 doi:10.1107/S1600536806004417 Acta Cryst.(2006). E62, m496–m497 Acta Crystallographica Section E

Structure Reports Online

ISSN 1600-5368

Potassium 3,5-dinitrobenzoate

Yan-Ping Duaand Man-Cheng Hub*

a

School of Environment and Chemical Engineering, Xi’an University of Engineering Science and Technology, Xi’an 710068, People’s Republic of China, andb_{School of}

Chemistry and Materials Science, ShaanXi Nomal University, Xi’an 710062, People’s Republic of China

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 298 K

Mean(C–C) = 0.004 A˚

Rfactor = 0.036

wRfactor = 0.129

Data-to-parameter ratio = 10.8

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 2 December 2005 Accepted 6 February 2006

#2006 International Union of Crystallography All rights reserved

The title compound, K+C7H3N2O6

, crystallized from aqueous solution, is not isostructural with sodium 3,5-dinitro-benzoate. Both the anion and the cation lie on a twofold axis. The K+cation is surrounded by eight O atoms and the crystal structure is stabilized by–interactions.

Comment

During work on crystallization, potassium 3,5-dinitro-benzoate, (I), was obtained as single crystals by evaporation of an aqueous solution at room temperature, and its structure determined. Probably due to the difference in the radii of K+ and Na+_{cations, compound (I) is not isostructural with the Na}

salt, sodium 3,5-dinitrobenzoate, whose structure has been reported in the space groupP3121 (Joneset al., 2005).

The structure of (I) is shown in Fig. 1. The K+cation and 3,5-dinitrobenzoate anion lie on a twofold axis. All atoms of the 3,5-dinitrobenzoate anion are almost coplanar, as observed in the corresponding Na+_{salt. The crystal structure is essentially}

Figure 1

The ions and complete coordination of the K+ cation of the title compound. Displacement ellipsoids are drawn at the 30% probability level. Atoms with the suffixes A, B, C, D and E are at the symmetry positions (1x,y,1

2z), ( 1 2x,

1 2+y,

1 2z), (

1 2+x,

1

2+y,z+ 1), (x+ 1,

y+ 1,z) and (x,y+ 1,1

ionic, and each K+ cation interacts with eight O atoms belonging to nitro and carboxylate groups of four symmetry-related anions (Table 1). The crystal packing is stabilized by intermolecular – interactions (4.05 A˚ ) between aromatic rings (Fig. 2), forming a layer structure.

Experimental

3,5-Dinitrobenzoic acid (14.1 mmol) was added to a solution of KOH (14.1 mmol) in water (10 ml). The mixture was stirred for 2 h at 298 K. The solution was then filtered under reduced pressure and set aside for crystallization. After 7 d, pure colourless crystals of (I) were collected from the filtered solution.

Crystal data

K+_C 7H3N2O6

Mr= 250.21

Monoclinic,C2=c a= 10.150 (3) A˚

b= 17.715 (4) A˚

c= 7.066 (2) A˚

= 133.075 (3)

V= 928.1 (4) A˚3

Z= 4

Dx= 1.791 Mg m

3

MoKradiation Cell parameters from 1239

reflections

= 3.0–27.6 = 0.59 mm1

T= 298 (2) K Block, colourless 0.450.320.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

’and!scans

Absorption correction: multi-scan (SADABS; Sheldrick, 2002)

Tmin= 0.777,Tmax= 0.867

2333 measured reflections

809 independent reflections 667 reflections withI> 2(I)

Rint= 0.019 max= 25.0

h=12!11

k=20!16

l=8!8

Refinement

Refinement onF2 R[F2_{> 2(F}2_{)] = 0.036}

wR(F2) = 0.129

S= 1.00 809 reflections 75 parameters

H-atom parameters constrained

w= 1/[2

(Fo2) + (0.0885P)2

+ 0.7104P]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001

max= 0.21 e A˚ 3

min=0.22 e A˚ 3

Table 1

Selected bond lengths (A˚ ).

K1—O1i

2.636 (2)

K1—O1 2.801 (2)

K1—O3ii

3.021 (3) K1—O2ii

3.034 (3)

Symmetry codes: (i)xþ1;yþ1;z; (ii)xþ1 2;yþ

1 2;zþ1.

H atoms were placed in calculated positions and refined as riding, with C—H distances constrained to 0.93 A˚ and with Uiso(H) = 1.2Ueq(C).

Data collection:SMART(Bruker, 2001); cell refinement:SAINT (Bruker, 2001); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL(Sheldrick, 2001); software used to prepare material for publication:SHELXTL.

Financial support from the National Natural Science Foundation of China (No. 20471035) is acknowledged.

References

Bruker (2001).SMARTandSAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Jones, H. P., Gillon, A. L. & Davey, R. J. (2005).Acta Cryst.E61, m1131– m1132.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97, University of Go¨ttingen, Germany.

Sheldrick, G. M. (2001).SHELXTL. Version 5. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2002).SADABS. University of Go¨ttingen, Germany.

Figure 2

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Acta Cryst. (2006). E62, m496–m497

supporting information

Acta Cryst. (2006). E62, m496–m497 [https://doi.org/10.1107/S1600536806004417]

Potassium 3,5-dinitrobenzoate

Yan-Ping Du and Man-Cheng Hu

Potassium 3,5-dinitrobenzoate

Crystal data

K+_·C7H3N2O6−

Mr = 250.21

Monoclinic, C2/c

Hall symbol: -C 2yc

a = 10.150 (3) Å

b = 17.715 (4) Å

c = 7.066 (2) Å

β = 133.075 (3)°

V = 928.1 (4) Å3

Z = 4

F(000) = 504

Dx = 1.791 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1239 reflections

θ = 3.0–27.6°

µ = 0.59 mm−1

T = 298 K Block, colourless 0.45 × 0.32 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

φ and ω scans

Absorption correction: multi-scan (SADABS; Sheldrick, 2002)

Tmin = 0.777, Tmax = 0.867

2333 measured reflections 809 independent reflections 667 reflections with I > 2σ(I)

Rint = 0.019

θmax = 25.0°, θmin = 2.3°

h = −12→11

k = −20→16

l = −8→8

Refinement

Refinement on F2 Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.036}

wR(F2_{) = 0.129}

S = 1.00 809 reflections 75 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2_(F

o2) + (0.0885P)2 + 0.7104P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001 Δρmax = 0.21 e Å−3 Δρmin = −0.22 e Å−3

Special details

Refinement. Refinement of F2 _{against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F}2_, conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

K1 0.5000 0.54552 (4) 0.2500 0.0465 (4)

N1 0.3593 (4) 0.12417 (16) −0.2004 (5) 0.0606 (7)

O1 0.4719 (4) 0.40028 (12) 0.0686 (5) 0.0686 (7)

O2 0.2967 (4) 0.16050 (15) −0.3929 (5) 0.0737 (7)

O3 0.3584 (4) 0.05531 (14) −0.1966 (6) 0.0892 (9)

C1 0.5000 0.3686 (2) 0.2500 0.0465 (9)

C2 0.5000 0.2828 (2) 0.2500 0.0421 (8)

C3 0.4371 (4) 0.24349 (17) 0.0323 (5) 0.0455 (7)

H3 0.3964 0.2693 −0.1140 0.055*

C4 0.4355 (4) 0.16532 (16) 0.0351 (5) 0.0461 (7)

C5 0.5000 0.1243 (2) 0.2500 0.0506 (10)

H5 0.5000 0.0718 0.2500 0.061*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

K1 0.0830 (7) 0.0307 (5) 0.0366 (5) 0.000 0.0451 (5) 0.000

N1 0.0623 (16) 0.0551 (17) 0.0526 (16) 0.0056 (12) 0.0346 (13) −0.0065 (12)

O1 0.119 (2) 0.0469 (12) 0.0678 (14) 0.0015 (11) 0.0745 (15) 0.0050 (10)

O2 0.0925 (18) 0.0736 (16) 0.0507 (14) −0.0063 (12) 0.0472 (14) −0.0066 (11)

O3 0.107 (2) 0.0501 (15) 0.0717 (17) 0.0125 (13) 0.0463 (16) −0.0121 (11)

C1 0.058 (2) 0.043 (2) 0.049 (2) 0.000 0.041 (2) 0.000

C2 0.0463 (19) 0.041 (2) 0.045 (2) 0.000 0.0338 (17) 0.000

C3 0.0475 (14) 0.0479 (16) 0.0457 (16) 0.0039 (11) 0.0337 (13) 0.0025 (12)

C4 0.0449 (14) 0.0469 (16) 0.0434 (16) 0.0010 (11) 0.0288 (13) −0.0045 (11)

C5 0.048 (2) 0.042 (2) 0.054 (2) 0.000 0.032 (2) 0.000

Geometric parameters (Å, º)

K1—O1i _{2.636 (2) N1—K1}vi _{3.313 (3)}

K1—O1ii _{2.636 (2) O1—C1 1.241 (3)}

K1—O1 2.801 (2) O1—K1i _{2.636 (2)}

K1—O1iii _{2.801 (2) O2—K1}vi _{3.034 (3)}

K1—O3iv _{3.021 (3) O3—K1}vi _{3.021 (3)}

K1—O3v _{3.021 (3) C1—O1}iii _{1.241 (3)}

K1—O2iv _{3.034 (3) C1—C2 1.521 (6)}

K1—O2v _{3.034 (3) C2—C3 1.385 (3)}

K1—C1 3.134 (4) C2—C3iii _{1.385 (3)}

K1—N1iv _{3.313 (3) C3—C4 1.385 (4)}

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Acta Cryst. (2006). E62, m496–m497

K1—K1i _{3.8839 (11) C4—C5 1.380 (4)}

N1—O2 1.220 (4) C5—C4iii _{1.380 (4)}

N1—O3 1.220 (4) C5—H5 0.9300

N1—C4 1.463 (4)

O1i_—K1—O1ii _{137.28 (10) O1}iii_—K1—N1v _{127.54 (7)}

O1i_{—K1—O1 88.87 (7) O3}iv_—K1—N1v _{151.83 (7)}

O1ii_{—K1—O1 133.53 (7) O3}v_—K1—N1v _{21.58 (7)}

O1i_—K1—O1iii _{133.53 (7) O2}iv_—K1—N1v _{111.42 (8)}

O1ii_—K1—O1iii _{88.87 (7) O2}v_—K1—N1v _{21.58 (7)}

O1—K1—O1iii _{46.55 (9) C1—K1—N1}v _{114.87 (5)}

O1i_—K1—O3iv _{110.34 (10) N1}iv_—K1—N1v _{130.26 (10)}

O1ii_—K1—O3iv _{67.08 (9) O1}i_—K1—K1i _{46.14 (5)}

O1—K1—O3iv _{107.54 (8) O1}ii_—K1—K1i _{174.50 (6)}

O1iii_—K1—O3iv _{78.70 (8) O1—K1—K1}i _{42.74 (4)}

O1i_—K1—O3v _{67.08 (9) O1}iii_—K1—K1i _{88.37 (5)}

O1ii_—K1—O3v _{110.34 (10) O3}iv_—K1—K1i _{116.96 (6)}

O1—K1—O3v _{78.70 (8) O3}v_—K1—K1i _{66.07 (7)}

O1iii_—K1—O3v _{107.54 (8) O2}iv_—K1—K1i _{114.75 (5)}

O3iv_—K1—O3v _{173.42 (10) O2}v_—K1—K1i _{97.98 (5)}

O1i_—K1—O2iv _{80.84 (8) C1—K1—K1}i _{65.46 (2)}

O1ii_—K1—O2iv _{70.74 (8) N1}iv_—K1—K1i _{123.86 (5)}

O1—K1—O2iv _{136.92 (8) N1}v_—K1—K1i _{78.01 (6)}

O1iii_—K1—O2iv _{120.21 (7) O2—N1—O3 123.1 (3)}

O3iv_—K1—O2iv _{41.50 (7) O2—N1—C4 118.3 (3)}

O3v_—K1—O2iv _{132.21 (8) O3—N1—C4 118.6 (3)}

O1i_—K1—O2v _{70.74 (8) O2—N1—K1}vi _{66.21 (16)}

O1ii_—K1—O2v _{80.84 (8) O3—N1—K1}vi _{65.59 (17)}

O1—K1—O2v _{120.21 (7) C4—N1—K1}vi _{147.81 (18)}

O1iii_—K1—O2v _{136.92 (8) C1—O1—K1}i _{164.64 (19)}

O3iv_—K1—O2v _{132.21 (8) C1—O1—K1 93.6 (2)}

O3v_—K1—O2v _{41.50 (7) K1}i_{—O1—K1 91.13 (7)}

O2iv_—K1—O2v _{95.66 (11) N1—O2—K1}vi _{92.21 (19)}

O1i_{—K1—C1 111.36 (5) N1—O3—K1}vi _{92.83 (19)}

O1ii_{—K1—C1 111.36 (5) O1—C1—O1}iii _{126.3 (4)}

O1—K1—C1 23.27 (4) O1—C1—C2 116.87 (19)

O1iii_{—K1—C1 23.27 (4) O1}iii_{—C1—C2 116.87 (19)}

O3iv_{—K1—C1 93.29 (5) O1—C1—K1 63.13 (19)}

O3v_{—K1—C1 93.29 (5) O1}iii_{—C1—K1 63.13 (19)}

O2iv_{—K1—C1 132.17 (6) C2—C1—K1 180.0}

O2v_{—K1—C1 132.17 (6) C3—C2—C3}iii _{119.6 (4)}

O1i_—K1—N1iv _{99.99 (8) C3—C2—C1 120.18 (18)}

O1ii_—K1—N1iv _{61.33 (8) C3}iii_{—C2—C1 120.18 (18)}

O1—K1—N1iv _{127.54 (7) C2—C3—C4 119.2 (3)}

O1iii_—K1—N1iv _{99.40 (8) C2—C3—H3 120.4}

O3iv_—K1—N1iv _{21.58 (7) C4—C3—H3 120.4}

O3v_—K1—N1iv _{151.83 (7) C5—C4—C3 122.8 (3)}

O2v_—K1—N1iv _{111.42 (8) C3—C4—N1 118.9 (3)}

C1—K1—N1iv _{114.87 (5) C4—C5—C4}iii _{116.4 (4)}

O1i_—K1—N1v _{61.33 (8) C4—C5—H5 121.8}

O1ii_—K1—N1v _{99.99 (8) C4}iii_{—C5—H5 121.8}

O1—K1—N1v _{99.40 (8)}