Triethyl­ammonium 4-amino­benzene­sulfonate

In the title compound, C₆H₁₆N⁺·C₆H₆NO₃S⁻, the NH₂ group of the 4-amino­benzene­sulfonate anion forms N—H...O hydrogen bonds to O atoms of two other 4-amino­benzene­sulfonate anions, generating two-dimensional layers. The triethyl­ammonium cations lie between these layers, forming N—H...O hydrogen bonds to the sulfonate groups.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.055
• wR factor = 0.171
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.11
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.02 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O3      ..       5.36 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT245_ALERT_2_C U(iso) H1A     Smaller than U(eq) N1      by ...       0.02 AngSq
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A    ..  S1      ..       2.91 Ang.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         13

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Aminobenzenesulfonic acid and its derivatives, and their complexes, are widely used in the fields of biology, catalysis and materials science. The title compound (Fig. 1) consists of triethylammonium cations and 4-aminobenzenesulfonate anions. The bond lengths and angles of the triethylammonium cation agree with those in the compound triethylammonium 4-(2-chlorobenzoyl)-3-methyl-1-(p-tolyl)-1H-pyrazol-5-olate (Duan et al., 2005). The geometrical parameters of the 4-aminobenzenesulfonate anion are similar to those in a related compound (Sui et al., 2006). The NH₂ group of the 4-aminobenzenesulfonate anion forms N—H···O hydrogen bonds to O atoms of two other 4-aminobenzenesulfonate anions (Table 1), generating two-dimensional layers in the (202) planes. The triethylammonium cations lie between these layers, forming N—H···O hydrogen bonds to the sulfonate groups (Fig. 2 and Table 1).

Related literature

For related literature, see: Duan et al. (2005); Sui et al. (2006).

S2. Experimental

4-Aminobenzenesulfonic acid (0.02 mol) and triethylamine (0.02 mol) were stirred in ethanol (10 ml) for 0.5 h. The solution was then allowed to evaporate at room temperature. Colourless single crystals of the title compound were formed after 8 d.

S3. Refinement

H atoms bound to C atoms were positioned geometrically with C—H = 0.93–0.97 Å and refined as riding with U_iso(H) = 1.2 or 1.5U_eq(C). H atoms bound to N atoms were located in difference Fourier maps and refined with isotropic displacement parameters, with the N—H and H···H distances restrained to be 0.90 (1) and 1.50 (1) Å, respectively. The CH₂—CH₃ distances in the triethylammonium cation were restrained to be 1.54 (1) Å, and the anisotropic displacement parameters of one methyl group (C12) were restrained to be approximately isotropic.

Computing details

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

Figures

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 30% probability for non-H atoms.
	Fig. 2. The crystal packing of (I), viewed along the b axis. Hydrogen bonds are indicated by dashed lines.

Triethylammonium 4-aminobenzenesulfonate

Crystal data

C6H16N^+·C6H6NO3S^−	F(000) = 592
Mr = 274.38	Dx = 1.249 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1829 reflections
a = 13.003 (3) Å	θ = 2.5–23.6°
b = 8.7648 (19) Å	µ = 0.23 mm^−1
c = 13.041 (3) Å	T = 294 K
β = 101.053 (4)°	Block, colourless
V = 1458.8 (6) Å^3	0.20 × 0.18 × 0.16 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	2575 independent reflections
Radiation source: fine-focus sealed tube	1770 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→15
Tmin = 0.956, Tmax = 0.965	k = −10→8
5906 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0918P)^2 + 0.6965P] where P = (Fo^2 + 2Fc^2)/3
2575 reflections	(Δ/σ)max = 0.005
178 parameters	Δρmax = 0.77 e Å^−3
13 restraints	Δρmin = −0.36 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.53476 (4)	0.08476 (6)	0.74545 (5)	0.04679 (15)
O1	0.58857 (13)	0.20384 (19)	0.81109 (15)	0.0704 (6)
O2	0.51159 (12)	−0.04414 (18)	0.80888 (13)	0.0597 (5)
O3	0.58690 (12)	0.0356 (2)	0.66309 (13)	0.0710 (5)
N1	0.12768 (17)	0.3574 (4)	0.54777 (18)	0.0954 (9)
C1	0.41219 (16)	0.1618 (2)	0.68650 (16)	0.0416 (5)
C2	0.37541 (17)	0.1483 (3)	0.57977 (17)	0.0486 (6)
H2	0.4149	0.0960	0.5388	0.058*
C3	0.28124 (17)	0.2116 (3)	0.53432 (18)	0.0561 (7)
H3	0.2573	0.2002	0.4628	0.067*
C4	0.22033 (17)	0.2931 (3)	0.59351 (19)	0.0552 (7)
C5	0.25780 (17)	0.3034 (3)	0.70101 (19)	0.0553 (6)
H5	0.2189	0.3550	0.7429	0.066*
C6	0.35140 (17)	0.2379 (3)	0.74524 (18)	0.0500 (6)
H6	0.3745	0.2452	0.8171	0.060*
N2	0.56177 (17)	0.6596 (2)	0.76858 (16)	0.0603 (6)
C7	0.4596 (2)	0.5954 (3)	0.7160 (3)	0.0841 (10)
H7A	0.4096	0.6059	0.7621	0.101*
H7B	0.4682	0.4874	0.7039	0.101*
C8	0.4161 (3)	0.6719 (5)	0.6135 (3)	0.1167 (14)
H8A	0.4143	0.7803	0.6236	0.175*
H8B	0.3463	0.6353	0.5876	0.175*
H8C	0.4598	0.6488	0.5640	0.175*
C9	0.64448 (19)	0.6546 (3)	0.7037 (2)	0.0642 (8)
H9A	0.7086	0.6972	0.7439	0.077*
H9B	0.6229	0.7188	0.6428	0.077*
C10	0.6674 (2)	0.4968 (3)	0.6677 (3)	0.0821 (9)
H10A	0.6866	0.4312	0.7272	0.123*
H10B	0.7241	0.5018	0.6302	0.123*
H10C	0.6061	0.4570	0.6227	0.123*
C11	0.5883 (3)	0.5882 (3)	0.8744 (3)	0.1043 (13)
H11A	0.5261	0.5885	0.9053	0.125*
H11B	0.6078	0.4827	0.8666	0.125*
C12	0.6733 (3)	0.6642 (5)	0.9464 (3)	0.1266 (7)
H12A	0.7381	0.6491	0.9228	0.190*
H12B	0.6788	0.6218	1.0151	0.190*
H12C	0.6588	0.7714	0.9484	0.190*
H1A	0.0925 (9)	0.4126 (17)	0.5859 (7)	0.072 (8)*
H1B	0.1053 (16)	0.360 (3)	0.4789 (5)	0.089 (9)*
H2A	0.5441 (14)	0.7566 (10)	0.7800 (17)	0.063 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0478 (3)	0.0379 (3)	0.0537 (3)	−0.0020 (2)	0.0074 (2)	0.0007 (3)
O1	0.0679 (10)	0.0462 (9)	0.0846 (12)	−0.0089 (8)	−0.0168 (9)	−0.0054 (9)
O2	0.0696 (9)	0.0404 (8)	0.0711 (10)	0.0057 (8)	0.0185 (8)	0.0104 (8)
O3	0.0567 (9)	0.0946 (13)	0.0660 (10)	0.0160 (9)	0.0226 (8)	−0.0002 (10)
N1	0.0629 (13)	0.159 (3)	0.0639 (14)	0.0444 (15)	0.0111 (11)	0.0076 (16)
C1	0.0452 (11)	0.0350 (11)	0.0460 (11)	−0.0065 (9)	0.0120 (9)	−0.0001 (9)
C2	0.0522 (12)	0.0486 (12)	0.0479 (12)	−0.0010 (10)	0.0168 (10)	−0.0030 (11)
C3	0.0544 (12)	0.0726 (16)	0.0413 (12)	−0.0036 (12)	0.0094 (10)	−0.0015 (12)
C4	0.0439 (11)	0.0642 (15)	0.0577 (14)	0.0018 (11)	0.0105 (10)	0.0094 (12)
C5	0.0516 (12)	0.0622 (14)	0.0557 (13)	0.0019 (11)	0.0194 (10)	−0.0042 (12)
C6	0.0552 (12)	0.0505 (13)	0.0449 (12)	−0.0002 (11)	0.0112 (10)	−0.0034 (11)
N2	0.0832 (13)	0.0315 (10)	0.0681 (13)	0.0003 (10)	0.0191 (11)	−0.0016 (10)
C7	0.0700 (16)	0.0589 (16)	0.133 (2)	−0.0122 (14)	0.0426 (16)	−0.0206 (17)
C8	0.083 (2)	0.126 (3)	0.128 (3)	−0.006 (2)	−0.013 (2)	−0.041 (3)
C9	0.0573 (13)	0.0461 (13)	0.0907 (18)	−0.0047 (11)	0.0178 (13)	−0.0009 (14)
C10	0.0773 (17)	0.0616 (17)	0.112 (2)	0.0043 (14)	0.0301 (16)	−0.0158 (17)
C11	0.167 (3)	0.0500 (16)	0.097 (2)	0.0111 (19)	0.026 (2)	0.0188 (17)
C12	0.1284 (9)	0.1245 (10)	0.1254 (10)	0.0019 (7)	0.0203 (7)	0.0000 (7)

Geometric parameters (Å, º)

S1—O3	1.4416 (18)	N2—H2A	0.901 (8)
S1—O1	1.4429 (17)	C7—C8	1.505 (4)
S1—O2	1.4653 (17)	C7—H7A	0.970
S1—C1	1.766 (2)	C7—H7B	0.970
N1—C4	1.360 (3)	C8—H8A	0.960
N1—H1A	0.883 (8)	C8—H8B	0.960
N1—H1B	0.889 (7)	C8—H8C	0.960
C1—C6	1.374 (3)	C9—C10	1.509 (3)
C1—C2	1.387 (3)	C9—H9A	0.970
C2—C3	1.371 (3)	C9—H9B	0.970
C2—H2	0.930	C10—H10A	0.960
C3—C4	1.403 (3)	C10—H10B	0.960
C3—H3	0.930	C10—H10C	0.960
C4—C5	1.396 (3)	C11—C12	1.466 (5)
C5—C6	1.369 (3)	C11—H11A	0.970
C5—H5	0.930	C11—H11B	0.970
C6—H6	0.930	C12—H12A	0.960
N2—C7	1.484 (3)	C12—H12B	0.960
N2—C9	1.491 (3)	C12—H12C	0.960
N2—C11	1.494 (4)
O3—S1—O1	114.48 (12)	C8—C7—H7A	109.0
O3—S1—O2	111.54 (11)	N2—C7—H7B	109.0
O1—S1—O2	110.59 (11)	C8—C7—H7B	109.0
O3—S1—C1	107.70 (10)	H7A—C7—H7B	107.8
O1—S1—C1	106.05 (10)	C7—C8—H8A	109.5
O2—S1—C1	105.92 (10)	C7—C8—H8B	109.5
C4—N1—H1A	119.4 (8)	H8A—C8—H8B	109.5
C4—N1—H1B	122.9 (13)	C7—C8—H8C	109.5
H1A—N1—H1B	116.8 (13)	H8A—C8—H8C	109.5
C6—C1—C2	118.42 (19)	H8B—C8—H8C	109.5
C6—C1—S1	120.70 (16)	N2—C9—C10	114.2 (2)
C2—C1—S1	120.87 (17)	N2—C9—H9A	108.7
C3—C2—C1	120.5 (2)	C10—C9—H9A	108.7
C3—C2—H2	119.8	N2—C9—H9B	108.7
C1—C2—H2	119.8	C10—C9—H9B	108.7
C2—C3—C4	121.3 (2)	H9A—C9—H9B	107.6
C2—C3—H3	119.3	C9—C10—H10A	109.5
C4—C3—H3	119.3	C9—C10—H10B	109.5
N1—C4—C5	121.6 (2)	H10A—C10—H10B	109.5
N1—C4—C3	121.1 (2)	C9—C10—H10C	109.5
C5—C4—C3	117.4 (2)	H10A—C10—H10C	109.5
C6—C5—C4	120.5 (2)	H10B—C10—H10C	109.5
C6—C5—H5	119.8	C12—C11—N2	114.4 (3)
C4—C5—H5	119.8	C12—C11—H11A	108.7
C5—C6—C1	121.9 (2)	N2—C11—H11A	108.7
C5—C6—H6	119.0	C12—C11—H11B	108.7
C1—C6—H6	119.0	N2—C11—H11B	108.7
C7—N2—C9	114.0 (2)	H11A—C11—H11B	107.6
C7—N2—C11	107.2 (2)	C11—C12—H12A	109.5
C9—N2—C11	116.6 (2)	C11—C12—H12B	109.5
C7—N2—H2A	101.6 (12)	H12A—C12—H12B	109.5
C9—N2—H2A	110.8 (13)	C11—C12—H12C	109.5
C11—N2—H2A	105.3 (15)	H12A—C12—H12C	109.5
N2—C7—C8	113.1 (3)	H12B—C12—H12C	109.5
N2—C7—H7A	109.0
O3—S1—C1—C6	−170.54 (18)	N1—C4—C5—C6	−179.9 (3)
O1—S1—C1—C6	−47.6 (2)	C3—C4—C5—C6	1.1 (4)
O2—S1—C1—C6	70.00 (19)	C4—C5—C6—C1	0.7 (4)
O3—S1—C1—C2	8.8 (2)	C2—C1—C6—C5	−1.7 (3)
O1—S1—C1—C2	131.77 (19)	S1—C1—C6—C5	177.65 (18)
O2—S1—C1—C2	−110.67 (19)	C9—N2—C7—C8	−56.8 (3)
C6—C1—C2—C3	0.9 (3)	C11—N2—C7—C8	172.6 (3)
S1—C1—C2—C3	−178.47 (18)	C7—N2—C9—C10	−57.7 (3)
C1—C2—C3—C4	1.0 (4)	C11—N2—C9—C10	68.1 (3)
C2—C3—C4—N1	179.1 (3)	C7—N2—C11—C12	−166.1 (3)
C2—C3—C4—C5	−1.9 (4)	C9—N2—C11—C12	64.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2^i	0.88 (1)	2.14 (1)	2.970 (3)	157 (2)
N1—H1B···O1^ii	0.89 (1)	2.23 (1)	3.078 (3)	160 (2)
N2—H2A···O2^iii	0.90 (1)	1.85 (1)	2.752 (2)	178 (2)
N2—H2A···S1^iii	0.90 (1)	2.91 (1)	3.750 (2)	156 (2)

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x, y+1, z.