Triethyl-ammonium 4-nitro-benzene-sulfonate.

In the anion of the title molecular salt, C(6)H(16)N(+)·C(6)H(4)O(5)S(-), the nitro group is twisted slightly from the benzene ring, making a dihedral angle of 3.16 (10)°. In the crystal structure, the cations and anions are linked into a two-dimensional network parallel to the ab plane by C-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For general background to and the synthesis of the title compound, see: Dann & Davies (1929 ▶); D’Souza et al. (2008 ▶); Hunig et al. (1965 ▶); Kim et al. (1999 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For a related structure, see: Quah et al. (2008 ▶).

Experimental

Crystal data

C6H16N+·n class="Chemical">C6H4NO5S−

M = 304.36

Orthorhombic,

a = 7.8015 (14) Å

b = 12.669 (2) Å

c = 29.910 (6) Å

V = 2956.3 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.22 × 0.18 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.950, T max = 0.967

21787 measured reflections

5605 independent reflections

3985 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.135

S = 1.01

5605 reflections

261 parameters

All H-atom parameters refined

Δρmax = 0.55 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810021379/wn2392sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021379/wn2392Isup2.hkl

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

C6H16N+·C6H4NO5S−	F(000) = 1296
Mr = 304.36	Dx = 1.368 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2801 reflections
a = 7.8015 (14) Å	θ = 2.7–30.9°
b = 12.669 (2) Å	µ = 0.24 mm−1
c = 29.910 (6) Å	T = 100 K
V = 2956.3 (9) Å3	Block, yellow
Z = 8	0.22 × 0.18 × 0.14 mm

Bruker SMART APEXII DUO CCD area-detector diffractometer	5605 independent reflections
Radiation source: fine-focus sealed tube	3985 reflections with I > 2σ(I)
graphite	Rint = 0.064
φ and ω scans	θmax = 33.2°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→12
Tmin = 0.950, Tmax = 0.967	k = −9→19
21787 measured reflections	l = −40→46

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	All H-atom parameters refined
S = 1.01	w = 1/[σ2(Fo2) + (0.0731P)2] where P = (Fo2 + 2Fc2)/3
5605 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
S1	0.38577 (5)	0.17193 (3)	0.095990 (11)	0.01330 (9)
O1	0.2417 (3)	−0.17343 (11)	0.26000 (4)	0.0524 (5)
O2	0.37185 (19)	−0.05239 (12)	0.29767 (4)	0.0372 (3)
O3	0.25347 (14)	0.13583 (9)	0.06573 (3)	0.0195 (2)
O4	0.55993 (14)	0.14889 (8)	0.07988 (3)	0.0172 (2)
O5	0.36886 (15)	0.28080 (8)	0.11063 (4)	0.0206 (2)
N1	0.3145 (2)	−0.08793 (12)	0.26271 (4)	0.0265 (3)
C1	0.3331 (2)	−0.02431 (12)	0.22174 (5)	0.0184 (3)
C2	0.2606 (2)	−0.06215 (11)	0.18258 (5)	0.0174 (3)
C3	0.27633 (19)	−0.00053 (11)	0.14418 (5)	0.0157 (3)
C4	0.36392 (18)	0.09467 (10)	0.14563 (4)	0.0134 (2)
C5	0.4376 (2)	0.13060 (12)	0.18557 (5)	0.0187 (3)
C6	0.4220 (2)	0.07070 (13)	0.22423 (5)	0.0214 (3)
N2	0.79571 (17)	0.31410 (9)	0.08449 (4)	0.0151 (2)
C7	0.7094 (2)	0.42076 (11)	0.08501 (5)	0.0192 (3)
C8	0.6060 (2)	0.44251 (13)	0.04323 (6)	0.0239 (3)
C9	0.8950 (2)	0.29787 (13)	0.12722 (5)	0.0212 (3)
C10	0.9187 (2)	0.18278 (14)	0.13903 (6)	0.0242 (3)
C11	0.9015 (2)	0.29386 (12)	0.04305 (5)	0.0166 (3)
C12	1.0456 (2)	0.37245 (13)	0.03620 (5)	0.0206 (3)
H2A	0.195 (3)	−0.1264 (16)	0.1819 (6)	0.023 (5)*
H3A	0.215 (3)	−0.0242 (14)	0.1159 (6)	0.021 (5)*
H5A	0.498 (3)	0.2009 (16)	0.1862 (6)	0.022 (5)*
H6A	0.471 (3)	0.0962 (17)	0.2514 (7)	0.035 (6)*
H7A	0.641 (3)	0.4184 (16)	0.1120 (7)	0.027 (5)*
H7B	0.807 (3)	0.4712 (16)	0.0893 (6)	0.020 (5)*
H8A	0.679 (3)	0.4491 (16)	0.0171 (6)	0.027 (5)*
H8B	0.517 (3)	0.3859 (17)	0.0374 (7)	0.028 (5)*
H8C	0.529 (3)	0.5072 (17)	0.0482 (7)	0.028 (5)*
H9A	1.007 (3)	0.3338 (14)	0.1233 (6)	0.020 (5)*
H9B	0.830 (3)	0.3364 (16)	0.1497 (7)	0.027 (5)*
H10A	0.981 (3)	0.1804 (17)	0.1669 (8)	0.039 (6)*
H10B	0.989 (3)	0.1457 (18)	0.1178 (7)	0.036 (6)*
H10C	0.817 (4)	0.147 (2)	0.1432 (7)	0.042 (6)*
H11A	0.825 (3)	0.2928 (14)	0.0187 (6)	0.014 (4)*
H11B	0.954 (3)	0.2213 (15)	0.0474 (6)	0.016 (4)*
H12A	1.143 (3)	0.3620 (15)	0.0569 (6)	0.021 (5)*
H12B	1.008 (3)	0.4425 (17)	0.0365 (6)	0.026 (5)*
H12C	1.100 (3)	0.3593 (19)	0.0071 (8)	0.036 (6)*
H1N2	0.702 (3)	0.2662 (15)	0.0832 (6)	0.017 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01496 (15)	0.01173 (14)	0.01322 (16)	0.00071 (12)	−0.00004 (11)	0.00010 (10)
O1	0.0965 (15)	0.0357 (8)	0.0251 (7)	−0.0290 (9)	−0.0008 (8)	0.0093 (5)
O2	0.0421 (8)	0.0529 (9)	0.0166 (6)	−0.0118 (7)	−0.0060 (5)	0.0093 (5)
O3	0.0202 (5)	0.0233 (5)	0.0152 (5)	−0.0025 (4)	−0.0050 (4)	0.0020 (4)
O4	0.0169 (5)	0.0156 (4)	0.0191 (5)	0.0004 (4)	0.0036 (4)	−0.0003 (4)
O5	0.0293 (6)	0.0124 (4)	0.0199 (5)	0.0041 (4)	0.0022 (4)	−0.0009 (4)
N1	0.0325 (8)	0.0300 (7)	0.0170 (6)	−0.0024 (6)	0.0024 (6)	0.0060 (5)
C1	0.0217 (7)	0.0208 (6)	0.0127 (6)	0.0010 (6)	0.0023 (5)	0.0034 (5)
C2	0.0213 (7)	0.0147 (6)	0.0163 (6)	−0.0011 (6)	0.0024 (5)	−0.0002 (5)
C3	0.0182 (6)	0.0154 (6)	0.0135 (6)	0.0005 (5)	0.0006 (5)	−0.0010 (4)
C4	0.0138 (6)	0.0139 (5)	0.0126 (6)	0.0020 (5)	0.0004 (5)	−0.0007 (4)
C5	0.0218 (7)	0.0177 (6)	0.0165 (7)	−0.0038 (6)	−0.0013 (5)	−0.0013 (5)
C6	0.0248 (8)	0.0255 (7)	0.0139 (6)	−0.0031 (6)	−0.0035 (6)	−0.0012 (5)
N2	0.0185 (6)	0.0132 (5)	0.0136 (5)	−0.0021 (5)	0.0002 (4)	0.0006 (4)
C7	0.0242 (7)	0.0130 (6)	0.0203 (7)	0.0007 (6)	0.0035 (6)	−0.0009 (5)
C8	0.0271 (8)	0.0218 (7)	0.0229 (8)	0.0061 (7)	0.0008 (6)	0.0042 (6)
C9	0.0294 (8)	0.0224 (7)	0.0119 (6)	−0.0032 (6)	−0.0020 (6)	0.0014 (5)
C10	0.0215 (8)	0.0275 (8)	0.0234 (8)	0.0041 (7)	−0.0023 (6)	0.0059 (6)
C11	0.0215 (7)	0.0165 (6)	0.0117 (6)	0.0018 (6)	0.0004 (5)	−0.0013 (5)
C12	0.0199 (7)	0.0234 (7)	0.0183 (7)	−0.0008 (6)	0.0025 (6)	0.0018 (5)

S1—O3	1.4468 (11)	N2—H1N2	0.95 (2)
S1—O5	1.4531 (11)	C7—C8	1.513 (2)
S1—O4	1.4709 (11)	C7—H7A	0.97 (2)
S1—C4	1.7865 (14)	C7—H7B	1.00 (2)
O1—N1	1.226 (2)	C8—H8A	0.97 (2)
O2—N1	1.2233 (19)	C8—H8B	1.01 (2)
N1—C1	1.4738 (19)	C8—H8C	1.03 (2)
C1—C2	1.386 (2)	C9—C10	1.512 (2)
C1—C6	1.391 (2)	C9—H9A	0.99 (2)
C2—C3	1.394 (2)	C9—H9B	0.97 (2)
C2—H2A	0.96 (2)	C10—H10A	0.97 (2)
C3—C4	1.387 (2)	C10—H10B	0.96 (2)
C3—H3A	1.015 (19)	C10—H10C	0.92 (3)
C4—C5	1.402 (2)	C11—C12	1.516 (2)
C5—C6	1.388 (2)	C11—H11A	0.943 (18)
C5—H5A	1.01 (2)	C11—H11B	1.014 (19)
C6—H6A	0.96 (2)	C12—H12A	0.99 (2)
N2—C9	1.5087 (19)	C12—H12B	0.93 (2)
N2—C7	1.5101 (19)	C12—H12C	0.98 (2)
N2—C11	1.5110 (19)
O3—S1—O5	115.07 (7)	C8—C7—H7A	113.7 (13)
O3—S1—O4	113.04 (7)	N2—C7—H7B	103.5 (12)
O5—S1—O4	111.77 (7)	C8—C7—H7B	113.2 (11)
O3—S1—C4	106.18 (6)	H7A—C7—H7B	109.3 (16)
O5—S1—C4	105.13 (6)	C7—C8—H8A	111.7 (13)
O4—S1—C4	104.57 (6)	C7—C8—H8B	112.2 (11)
O2—N1—O1	123.45 (14)	H8A—C8—H8B	108.7 (16)
O2—N1—C1	118.27 (14)	C7—C8—H8C	109.8 (11)
O1—N1—C1	118.28 (14)	H8A—C8—H8C	113.0 (16)
C2—C1—C6	123.21 (13)	H8B—C8—H8C	101.0 (17)
C2—C1—N1	118.25 (14)	N2—C9—C10	113.09 (13)
C6—C1—N1	118.53 (13)	N2—C9—H9A	106.9 (11)
C1—C2—C3	117.81 (14)	C10—C9—H9A	111.2 (11)
C1—C2—H2A	121.8 (11)	N2—C9—H9B	104.5 (13)
C3—C2—H2A	120.3 (11)	C10—C9—H9B	112.7 (12)
C4—C3—C2	120.31 (13)	H9A—C9—H9B	108.0 (16)
C4—C3—H3A	120.9 (11)	C9—C10—H10A	107.0 (13)
C2—C3—H3A	118.6 (11)	C9—C10—H10B	112.8 (13)
C3—C4—C5	120.74 (13)	H10A—C10—H10B	106 (2)
C3—C4—S1	119.83 (10)	C9—C10—H10C	113.7 (16)
C5—C4—S1	119.42 (11)	H10A—C10—H10C	107.5 (19)
C6—C5—C4	119.75 (14)	H10B—C10—H10C	110 (2)
C6—C5—H5A	120.6 (10)	N2—C11—C12	113.86 (12)
C4—C5—H5A	119.6 (10)	N2—C11—H11A	106.8 (11)
C5—C6—C1	118.18 (14)	C12—C11—H11A	112.1 (11)
C5—C6—H6A	119.3 (14)	N2—C11—H11B	105.6 (10)
C1—C6—H6A	122.6 (14)	C12—C11—H11B	108.3 (11)
C9—N2—C7	110.01 (12)	H11A—C11—H11B	109.9 (15)
C9—N2—C11	113.05 (12)	C11—C12—H12A	113.4 (11)
C7—N2—C11	113.83 (11)	C11—C12—H12B	113.1 (13)
C9—N2—H1N2	110.1 (11)	H12A—C12—H12B	111.1 (17)
C7—N2—H1N2	103.1 (11)	C11—C12—H12C	109.2 (14)
C11—N2—H1N2	106.2 (11)	H12A—C12—H12C	101.6 (17)
N2—C7—C8	113.10 (12)	H12B—C12—H12C	107.7 (18)
N2—C7—H7A	103.1 (12)
O2—N1—C1—C2	−176.81 (16)	O5—S1—C4—C5	−38.73 (14)
O1—N1—C1—C2	2.8 (2)	O4—S1—C4—C5	79.13 (13)
O2—N1—C1—C6	3.1 (2)	C3—C4—C5—C6	−0.4 (2)
O1—N1—C1—C6	−177.33 (18)	S1—C4—C5—C6	−179.65 (12)
C6—C1—C2—C3	−0.9 (2)	C4—C5—C6—C1	0.3 (2)
N1—C1—C2—C3	178.93 (14)	C2—C1—C6—C5	0.4 (3)
C1—C2—C3—C4	0.8 (2)	N1—C1—C6—C5	−179.46 (15)
C2—C3—C4—C5	−0.1 (2)	C9—N2—C7—C8	−179.61 (14)
C2—C3—C4—S1	179.10 (11)	C11—N2—C7—C8	52.33 (18)
O3—S1—C4—C3	19.67 (13)	C7—N2—C9—C10	154.66 (14)
O5—S1—C4—C3	142.05 (12)	C11—N2—C9—C10	−76.86 (17)
O4—S1—C4—C3	−100.09 (12)	C9—N2—C11—C12	−66.52 (16)
O3—S1—C4—C5	−161.10 (12)	C7—N2—C11—C12	59.96 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O4	0.95 (2)	1.86 (2)	2.7899 (17)	166 (2)
C2—H2A···O5i	0.96 (2)	2.485 (19)	3.1000 (19)	121.7 (14)
C7—H7B···O4ii	1.00 (2)	2.50 (2)	3.4081 (19)	151.3 (16)
C10—H10B···O3iii	0.96 (2)	2.59 (2)	3.461 (2)	151.1 (18)
C12—H12A···O5iii	0.99 (2)	2.60 (2)	3.559 (2)	164.1 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O4	0.95 (2)	1.86 (2)	2.7899 (17)	166 (2)
C2—H2A⋯O5i	0.96 (2)	2.485 (19)	3.1000 (19)	121.7 (14)
C7—H7B⋯O4ii	1.00 (2)	2.50 (2)	3.4081 (19)	151.3 (16)
C10—H10B⋯O3iii	0.96 (2)	2.59 (2)	3.461 (2)	151.1 (18)
C12—H12A⋯O5iii	0.99 (2)	2.60 (2)	3.559 (2)	164.1 (16)

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