2-Methyl-4-oxopentan-2-aminium 2-sulfamoylbenzoate.

In the title salt, C(6)H(14)NO(+)·C(7)H(6)NO(4)S(-), the 2-sulfamoylbenzoate anion has two intra-molecular hydrogen bonds, forming a five membered C-H⋯O and a seven-membered N-H⋯O twisted ring with ring motifs S(5) and S(7), respectively, while the 2-methyl-4-oxopentan-2-aminium cation also has a stabilizing intra-molecular N-H⋯O hydrogen bond with a twisted S(6) ring motif. The anions form inversion-related dimers with R(2) (2)(8) ring motifs through inter-molecular N-H⋯O hydrogen bonding. The dimers and cations are further linked and stabilized through inter-molecular N-H⋯O and C-H⋯O bonds, forming zigzag-shaped layers that extend along the crystallographic a axis.

Related literature

For related structures, see: Akram et al. (2008 ▶); Schmidt et al. (1997 ▶); Siddiqui et al. (2007 ▶). For the definition of hydrogen-bond patterns used for graph-set analysis, see: Bernstein et al. (1995 ▶). For applications of aldol condensation, see: Afonso & Crespo (2005 ▶).

Experimental

Crystal data

C6H14NO+·C7H6NO4S−

M = 316.37

Orthorhombic,

a = 21.1917 (9) Å

b = 6.3897 (2) Å

c = 23.3751 (11) Å

V = 3165.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.28 × 0.10 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.983

32870 measured reflections

4111 independent reflections

2961 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.110

S = 1.04

4111 reflections

200 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027007/si2187sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027007/si2187Isup2.hkl

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

C6H14NO+·C7H6NO4S−	F(000) = 1344
Mr = 316.37	Dx = 1.328 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4111 reflections
a = 21.1917 (9) Å	θ = 2.6–28.8°
b = 6.3897 (2) Å	µ = 0.23 mm−1
c = 23.3751 (11) Å	T = 296 K
V = 3165.2 (2) Å3	Needle, colorless
Z = 8	0.28 × 0.10 × 0.08 mm

Bruker Kappa APEXII CCD diffractometer	4111 independent reflections
Radiation source: fine-focus sealed tube	2961 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 7.40 pixels mm-1	θmax = 28.8°, θmin = 2.6°
ω scans	h = −27→28
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→5
Tmin = 0.975, Tmax = 0.983	l = −31→30
32870 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0482P)2 + 1.1665P] where P = (Fo2 + 2Fc2)/3
4111 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
O5	0.23168 (8)	0.6184 (3)	0.16582 (7)	0.0740 (6)
N2	0.17797 (6)	0.6721 (2)	0.27542 (6)	0.0367 (4)
C8	0.18387 (11)	0.5283 (3)	0.15179 (8)	0.0534 (6)
C9	0.12913 (9)	0.5023 (3)	0.19207 (8)	0.0451 (5)
C10	0.12064 (7)	0.6719 (3)	0.23730 (7)	0.0368 (5)
C11	0.11386 (9)	0.8877 (3)	0.21123 (9)	0.0504 (6)
C12	0.06400 (8)	0.6216 (3)	0.27479 (9)	0.0523 (6)
C13	0.17685 (15)	0.4323 (5)	0.09405 (10)	0.0902 (10)
S1	0.03137 (2)	0.12048 (7)	0.41313 (2)	0.0366 (1)
O1	0.18858 (5)	0.25236 (19)	0.31033 (5)	0.0426 (3)
O2	0.15851 (5)	−0.02972 (17)	0.35914 (5)	0.0413 (4)
O3	0.02610 (5)	0.1446 (2)	0.35274 (5)	0.0482 (4)
O4	−0.02263 (5)	0.1683 (2)	0.44799 (6)	0.0519 (4)
N1	0.04974 (8)	−0.1189 (2)	0.42641 (8)	0.0464 (5)
C1	0.15011 (7)	0.2984 (2)	0.40450 (6)	0.0307 (4)
C2	0.09432 (7)	0.2818 (2)	0.43663 (6)	0.0317 (4)
C3	0.08632 (8)	0.3954 (3)	0.48632 (7)	0.0408 (5)
C4	0.13337 (9)	0.5284 (3)	0.50512 (8)	0.0465 (6)
C5	0.18748 (9)	0.5514 (3)	0.47338 (8)	0.0473 (6)
C6	0.19563 (8)	0.4383 (3)	0.42347 (7)	0.0405 (5)
C7	0.16605 (7)	0.1638 (2)	0.35297 (7)	0.0324 (4)
H2A	0.18196	0.54745	0.29202	0.0441*
H2B	0.17365	0.77014	0.30218	0.0441*
H2C	0.21218	0.69889	0.25458	0.0441*
H9A	0.13377	0.36904	0.21148	0.0540*
H9B	0.09076	0.49517	0.16952	0.0540*
H11A	0.15160	0.92237	0.19057	0.0605*
H11B	0.10717	0.98862	0.24105	0.0605*
H11C	0.07852	0.88900	0.18554	0.0605*
H12A	0.06955	0.48618	0.29186	0.0628*
H12B	0.02641	0.62158	0.25188	0.0628*
H12C	0.06029	0.72529	0.30432	0.0628*
H13A	0.21496	0.45282	0.07257	0.1083*
H13B	0.14222	0.49701	0.07436	0.1083*
H13C	0.16884	0.28511	0.09803	0.1083*
H1A	0.0454 (10)	−0.141 (3)	0.4599 (10)	0.0557*
H1B	0.0843 (11)	−0.148 (3)	0.4094 (9)	0.0557*
H3	0.04917	0.38246	0.50721	0.0490*
H4	0.12842	0.60205	0.53914	0.0558*
H5	0.21875	0.64337	0.48550	0.0568*
H6	0.23233	0.45630	0.40221	0.0486*

	U11	U22	U33	U12	U13	U23
O5	0.0674 (10)	0.0762 (11)	0.0783 (11)	−0.0084 (8)	0.0259 (8)	−0.0127 (9)
N2	0.0321 (6)	0.0351 (7)	0.0430 (8)	−0.0012 (5)	−0.0019 (6)	−0.0067 (6)
C8	0.0666 (13)	0.0476 (10)	0.0461 (10)	0.0138 (10)	0.0033 (9)	−0.0028 (9)
C9	0.0520 (10)	0.0389 (8)	0.0443 (10)	−0.0064 (8)	−0.0092 (8)	−0.0041 (7)
C10	0.0326 (8)	0.0361 (8)	0.0417 (9)	−0.0027 (6)	−0.0045 (7)	−0.0009 (7)
C11	0.0517 (10)	0.0403 (9)	0.0593 (12)	0.0047 (8)	−0.0053 (9)	0.0025 (9)
C12	0.0348 (9)	0.0671 (12)	0.0550 (11)	−0.0065 (8)	−0.0003 (8)	0.0020 (10)
C13	0.110 (2)	0.110 (2)	0.0506 (13)	0.0401 (18)	−0.0048 (13)	−0.0204 (14)
S1	0.0269 (2)	0.0441 (2)	0.0389 (2)	−0.0018 (2)	0.0009 (2)	0.0023 (2)
O1	0.0429 (6)	0.0449 (6)	0.0401 (6)	0.0007 (5)	0.0096 (5)	−0.0001 (5)
O2	0.0435 (6)	0.0334 (6)	0.0469 (7)	0.0033 (5)	0.0055 (5)	−0.0053 (5)
O3	0.0396 (6)	0.0637 (8)	0.0412 (7)	−0.0052 (6)	−0.0085 (5)	0.0042 (6)
O4	0.0308 (6)	0.0665 (8)	0.0583 (8)	0.0012 (5)	0.0095 (5)	0.0013 (7)
N1	0.0480 (8)	0.0423 (8)	0.0489 (9)	−0.0057 (7)	0.0092 (7)	0.0034 (7)
C1	0.0286 (7)	0.0301 (7)	0.0335 (8)	0.0032 (5)	−0.0002 (6)	0.0007 (6)
C2	0.0293 (7)	0.0327 (7)	0.0332 (8)	0.0033 (6)	−0.0012 (6)	0.0027 (6)
C3	0.0397 (8)	0.0444 (9)	0.0383 (9)	0.0057 (7)	0.0050 (7)	−0.0009 (7)
C4	0.0569 (11)	0.0444 (9)	0.0382 (9)	0.0048 (8)	−0.0033 (8)	−0.0103 (8)
C5	0.0493 (10)	0.0416 (9)	0.0511 (10)	−0.0069 (8)	−0.0102 (8)	−0.0071 (8)
C6	0.0348 (8)	0.0415 (8)	0.0452 (10)	−0.0051 (7)	0.0017 (7)	−0.0012 (7)
C7	0.0230 (6)	0.0369 (8)	0.0373 (8)	0.0027 (6)	0.0001 (6)	−0.0021 (6)

S1—O4	1.4377 (13)	C11—H11B	0.9600
S1—N1	1.6086 (14)	C11—H11C	0.9600
S1—C2	1.7731 (15)	C11—H11A	0.9600
S1—O3	1.4244 (13)	C12—H12A	0.9600
O5—C8	1.211 (3)	C12—H12C	0.9600
O1—C7	1.2416 (19)	C12—H12B	0.9600
O2—C7	1.2551 (17)	C13—H13A	0.9600
N2—C10	1.507 (2)	C13—H13B	0.9600
N2—H2B	0.8900	C13—H13C	0.9600
N2—H2C	0.8900	C1—C7	1.518 (2)
N2—H2A	0.8900	C1—C2	1.405 (2)
N1—H1B	0.85 (2)	C1—C6	1.388 (2)
N1—H1A	0.80 (2)	C2—C3	1.380 (2)
C8—C9	1.503 (3)	C3—C4	1.382 (3)
C8—C13	1.490 (3)	C4—C5	1.374 (3)
C9—C10	1.525 (3)	C5—C6	1.383 (3)
C10—C11	1.514 (3)	C3—H3	0.9300
C10—C12	1.521 (2)	C4—H4	0.9300
C9—H9A	0.9700	C5—H5	0.9300
C9—H9B	0.9700	C6—H6	0.9300
S1···O2	3.1262 (12)	H1A···O4iv	2.21 (2)
O1···N2	2.8124 (18)	H1A···C4ii	3.01 (2)
O1···N2i	2.9878 (17)	H1B···O2	2.10 (2)
O2···N2ii	2.7622 (18)	H1B···C7	2.95 (2)
O2···S1	3.1262 (12)	H2A···O1	1.9400
O2···N1	2.848 (2)	H2A···H12A	2.4100
O2···O3	3.0227 (15)	H2A···C7	2.8600
O3···C7	2.9683 (18)	H2A···H9A	2.4300
O3···O2	3.0227 (15)	H2B···O2vii	1.8700
O4···C4iii	3.235 (2)	H2B···H11B	2.4400
O4···N1iv	3.008 (2)	H2B···H12C	2.4200
O5···C11	3.213 (3)	H2B···C7vii	2.7900
O5···C13v	3.255 (3)	H2C···O1v	2.5000
O5···C8v	3.189 (3)	H2C···H11A	2.4300
O5···N2	2.824 (2)	H2C···O5	2.1800
O1···H9A	2.6900	H2C···C8	2.7100
O1···H2Ci	2.5000	H3···H3iii	2.5900
O1···H2A	1.9400	H3···O4	2.4700
O1···H6	2.6800	H4···O4iii	2.7000
O1···H11Bii	2.9000	H5···C6v	2.9900
O2···H2Bii	1.8700	H5···H13Aix	2.5500
O2···H1B	2.10 (2)	H6···C7v	2.7800
O2···H12Cii	2.9000	H6···O1	2.6800
O2···H6i	2.5200	H6···O2v	2.5200
O3···H12Bvi	2.6900	H9A···O1	2.6900
O3···H11Cvi	2.8600	H9A···H2A	2.4300
O3···H9Bvi	2.7000	H9A···H11Bii	2.5900
O3···H12A	2.7600	H9A···H12A	2.4400
O4···H13Bvi	2.8100	H9B···H13B	2.4800
O4···H3	2.4700	H9B···O3x	2.7000
O4···H4iii	2.7000	H9B···H11C	2.5600
O4···H1Aiv	2.21 (2)	H9B···H12B	2.4900
O5···H11A	2.6400	H11A···O5	2.6400
O5···H2C	2.1800	H11A···H2C	2.4300
O5···H11Ai	2.8300	H11A···O5v	2.8300
O5···H13Cv	2.8400	H11A···C8	2.7600
N1···O2	2.848 (2)	H11B···H9Avii	2.5900
N1···C4ii	3.407 (2)	H11B···H12C	2.4500
N1···O4iv	3.008 (2)	H11B···O1vii	2.9000
N2···O1	2.8124 (18)	H11B···H2B	2.4400
N2···O1v	2.9878 (17)	H11C···H9B	2.5600
N2···O2vii	2.7622 (18)	H11C···H12B	2.5600
N2···O5	2.824 (2)	H11C···O3x	2.8600
C4···N1vii	3.407 (2)	H12A···H9A	2.4400
C4···O4iii	3.235 (2)	H12A···H2A	2.4100
C7···O3	2.9683 (18)	H12A···O3	2.7600
C8···O5i	3.189 (3)	H12B···H9B	2.4900
C11···O5	3.213 (3)	H12B···O3x	2.6900
C13···O5i	3.255 (3)	H12B···H11C	2.5600
C4···H13Cviii	3.0500	H12C···O2vii	2.9000
C4···H1Avii	3.01 (2)	H12C···H2B	2.4200
C6···H5i	2.9900	H12C···H11B	2.4500
C7···H1B	2.95 (2)	H13A···H5xi	2.5500
C7···H2Bii	2.7900	H13B···H9B	2.4800
C7···H2A	2.8600	H13B···O4x	2.8100
C7···H6i	2.7800	H13C···O5i	2.8400
C8···H2C	2.7100	H13C···C4xii	3.0500
C8···H11A	2.7600
O3—S1—C2	107.65 (7)	C10—C11—H11B	109.00
O3—S1—O4	118.44 (7)	H12A—C12—H12C	109.00
O3—S1—N1	108.25 (9)	H12A—C12—H12B	109.00
N1—S1—C2	108.12 (8)	C10—C12—H12C	109.00
O4—S1—N1	106.58 (9)	H12B—C12—H12C	109.00
O4—S1—C2	107.44 (7)	C10—C12—H12A	109.00
H2B—N2—H2C	109.00	C10—C12—H12B	109.00
H2A—N2—H2C	109.00	C8—C13—H13A	109.00
H2A—N2—H2B	109.00	H13A—C13—H13B	109.00
C10—N2—H2A	109.00	C8—C13—H13B	109.00
C10—N2—H2B	109.00	C8—C13—H13C	109.00
C10—N2—H2C	109.00	H13B—C13—H13C	109.00
H1A—N1—H1B	121 (2)	H13A—C13—H13C	109.00
S1—N1—H1B	109.0 (13)	C6—C1—C7	117.63 (13)
S1—N1—H1A	109.2 (14)	C2—C1—C7	124.66 (12)
C9—C8—C13	116.4 (2)	C2—C1—C6	117.57 (13)
O5—C8—C9	121.92 (18)	S1—C2—C1	120.76 (10)
O5—C8—C13	121.7 (2)	S1—C2—C3	118.30 (12)
C8—C9—C10	116.54 (16)	C1—C2—C3	120.91 (14)
N2—C10—C9	108.40 (13)	C2—C3—C4	120.16 (16)
C9—C10—C12	110.03 (15)	C3—C4—C5	119.76 (17)
C11—C10—C12	110.46 (15)	C4—C5—C6	120.26 (17)
N2—C10—C11	108.28 (14)	C1—C6—C5	121.28 (16)
N2—C10—C12	107.21 (13)	O1—C7—O2	126.17 (15)
C9—C10—C11	112.29 (15)	O1—C7—C1	117.67 (12)
C8—C9—H9B	108.00	O2—C7—C1	116.02 (13)
C8—C9—H9A	108.00	C2—C3—H3	120.00
H9A—C9—H9B	107.00	C4—C3—H3	120.00
C10—C9—H9A	108.00	C3—C4—H4	120.00
C10—C9—H9B	108.00	C5—C4—H4	120.00
C10—C11—H11C	109.00	C4—C5—H5	120.00
H11B—C11—H11C	109.00	C6—C5—H5	120.00
H11A—C11—H11B	109.00	C1—C6—H6	119.00
H11A—C11—H11C	109.00	C5—C6—H6	119.00
C10—C11—H11A	109.00
O4—S1—C2—C1	−168.62 (11)	C7—C1—C2—S1	−8.69 (19)
O4—S1—C2—C3	9.43 (15)	C7—C1—C2—C3	173.31 (14)
N1—S1—C2—C1	76.71 (14)	C2—C1—C6—C5	2.4 (2)
N1—S1—C2—C3	−105.24 (14)	C7—C1—C6—C5	−173.44 (16)
O3—S1—C2—C1	−40.02 (13)	C2—C1—C7—O1	135.91 (15)
O3—S1—C2—C3	138.03 (13)	C2—C1—C7—O2	−48.2 (2)
O5—C8—C9—C10	29.1 (3)	C6—C1—C7—O1	−48.5 (2)
C13—C8—C9—C10	−152.4 (2)	C6—C1—C7—O2	127.34 (15)
C8—C9—C10—C12	−179.37 (16)	S1—C2—C3—C4	−177.83 (14)
C8—C9—C10—N2	−62.4 (2)	C1—C2—C3—C4	0.2 (2)
C8—C9—C10—C11	57.2 (2)	C2—C3—C4—C5	1.7 (3)
C6—C1—C2—S1	175.74 (12)	C3—C4—C5—C6	−1.5 (3)
C6—C1—C2—C3	−2.3 (2)	C4—C5—C6—C1	−0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4iv	0.80 (2)	2.21 (2)	3.008 (2)	172 (2)
N1—H1B···O2	0.85 (2)	2.10 (2)	2.848 (2)	145.4 (18)
N2—H2A···O1	0.89	1.94	2.8124 (18)	167
N2—H2B···O2vii	0.89	1.87	2.7622 (18)	176
N2—H2C···O5	0.89	2.18	2.824 (2)	129
N2—H2C···O1v	0.89	2.50	2.9878 (17)	115
C3—H3···O4	0.93	2.47	2.870 (2)	106
C6—H6···O2v	0.93	2.52	3.444 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.80 (2)	2.21 (2)	3.008 (2)	172 (2)
N1—H1B⋯O2	0.85 (2)	2.10 (2)	2.848 (2)	145.4 (18)
N2—H2A⋯O1	0.89	1.94	2.8124 (18)	167
N2—H2B⋯O2ii	0.89	1.87	2.7622 (18)	176
N2—H2C⋯O5	0.89	2.18	2.824 (2)	129
N2—H2C⋯O1iii	0.89	2.50	2.9878 (17)	115
C3—H3⋯O4	0.93	2.47	2.870 (2)	106
C6—H6⋯O2iii	0.93	2.52	3.444 (2)	170

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