N-(Phenyl-sulfon-yl)-l-asparagine.

In the title compound, C(10)H(12)N(2)O(5)S, one of the sulfonyl O atoms is hydrogen bonded to the amido N atom of an adjacent mol-ecule. There is also a weak hydrogen-bonding inter-action between the other sulfonyl O atom and the secondary amino N atom. In addition, the amido O atom is also hydrogen bonded to a carboxyl O atom. These hydrogen-bonding inter-actions give rise to a layer structure parallel to the bc plane.

Related literature

For related compounds, see: Koroniak et al. (2003 ▶); Arshad et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C10H12N2O5S

M = 272.28

Monoclinic,

a = 10.5479 (6) Å

b = 5.1587 (3) Å

c = 11.0157 (7) Å

β = 92.011 (3)°

V = 599.03 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.25 × 0.21 × 0.13 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.932, T max = 0.964

6832 measured reflections

2732 independent reflections

2518 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.06

2732 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 1187 Friedel pairs

Flack parameter: −0.01 (6)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050247/om2295sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050247/om2295Isup2.hkl

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

C10H12N2O5S	F(000) = 284
Mr = 272.28	Dx = 1.510 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3825 reflections
a = 10.5479 (6) Å	θ = 2.6–27.4°
b = 5.1587 (3) Å	µ = 0.29 mm−1
c = 11.0157 (7) Å	T = 296 K
β = 92.011 (3)°	Block, colorless
V = 599.03 (6) Å3	0.25 × 0.21 × 0.13 mm
Z = 2

Bruker APEXII diffractometer	2732 independent reflections
Radiation source: fine-focus sealed tube	2518 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.6°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.932, Tmax = 0.964	k = −6→6
6832 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0464P)2 + 0.0133P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2732 reflections	Δρmax = 0.33 e Å−3
176 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983), 1187 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (6)

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
C1	0.91282 (16)	0.8736 (3)	0.28950 (15)	0.0323 (4)
C2	0.93349 (19)	0.7209 (4)	0.18909 (17)	0.0411 (4)
H2	0.8795	0.5838	0.1688	0.049*
C3	1.03713 (19)	0.7776 (5)	0.11920 (19)	0.0503 (5)
H3	1.0534	0.6766	0.0516	0.060*
C4	1.11535 (19)	0.9813 (5)	0.1493 (2)	0.0499 (5)
H4	1.1837	1.0187	0.1012	0.060*
C5	1.09413 (19)	1.1314 (5)	0.2501 (2)	0.0517 (5)
H5	1.1483	1.2683	0.2700	0.062*
C6	0.99250 (18)	1.0783 (4)	0.32109 (19)	0.0439 (4)
H6	0.9775	1.1783	0.3893	0.053*
C7	0.59899 (15)	0.9058 (3)	0.19546 (14)	0.0279 (3)
H7	0.6111	0.7183	0.1873	0.034*
C8	0.64948 (16)	1.0412 (3)	0.08415 (14)	0.0311 (3)
C9	0.45593 (16)	0.9649 (3)	0.20037 (16)	0.0333 (4)
H9A	0.4444	1.1370	0.2336	0.040*
H9B	0.4187	0.9630	0.1186	0.040*
C10	0.38860 (15)	0.7715 (3)	0.27662 (15)	0.0315 (4)
H1A	0.379 (3)	1.000 (7)	0.406 (3)	0.073 (9)*
H2A	0.312 (3)	0.722 (7)	0.433 (3)	0.090 (10)*
N1	0.66143 (14)	0.9939 (3)	0.30846 (13)	0.0300 (3)
H1B	0.6757 (17)	1.141 (5)	0.3130 (17)	0.027 (5)*
N2	0.3616 (2)	0.8376 (5)	0.38858 (16)	0.0575 (5)
O1	0.73791 (14)	0.5586 (3)	0.36312 (13)	0.0448 (3)
O2	0.79671 (14)	0.9371 (3)	0.49048 (11)	0.0458 (3)
O3	0.70376 (15)	1.2446 (3)	0.08654 (13)	0.0492 (4)
O4	0.61999 (16)	0.9065 (3)	−0.01409 (11)	0.0485 (4)
H4A	0.6403	0.9880	−0.0743	0.073*
O6	0.35901 (14)	0.5579 (3)	0.23573 (12)	0.0430 (3)
S1	0.77553 (4)	0.82468 (8)	0.37280 (3)	0.03153 (11)

	U11	U22	U33	U12	U13	U23
C1	0.0338 (7)	0.0321 (10)	0.0308 (8)	0.0042 (6)	−0.0010 (6)	0.0009 (6)
C2	0.0425 (9)	0.0410 (10)	0.0399 (10)	0.0005 (8)	0.0027 (8)	−0.0079 (8)
C3	0.0454 (10)	0.0652 (15)	0.0407 (10)	0.0089 (10)	0.0084 (8)	−0.0096 (10)
C4	0.0310 (9)	0.0658 (14)	0.0532 (12)	0.0041 (9)	0.0049 (8)	0.0057 (10)
C5	0.0355 (10)	0.0530 (13)	0.0662 (14)	−0.0071 (9)	−0.0025 (9)	−0.0011 (11)
C6	0.0412 (9)	0.0438 (11)	0.0466 (11)	−0.0015 (8)	−0.0012 (8)	−0.0101 (9)
C7	0.0340 (8)	0.0237 (7)	0.0263 (8)	−0.0001 (6)	0.0039 (6)	0.0008 (6)
C8	0.0357 (8)	0.0312 (9)	0.0268 (8)	−0.0011 (7)	0.0059 (7)	0.0014 (6)
C9	0.0340 (8)	0.0315 (9)	0.0346 (9)	0.0006 (7)	0.0041 (7)	0.0053 (7)
C10	0.0326 (8)	0.0314 (10)	0.0306 (8)	0.0005 (6)	0.0049 (6)	0.0018 (6)
N1	0.0365 (7)	0.0248 (7)	0.0287 (7)	0.0013 (6)	0.0026 (6)	−0.0003 (6)
N2	0.0810 (13)	0.0565 (11)	0.0363 (9)	−0.0212 (12)	0.0216 (8)	−0.0110 (10)
O1	0.0570 (8)	0.0306 (7)	0.0472 (8)	0.0007 (6)	0.0059 (6)	0.0108 (6)
O2	0.0567 (8)	0.0564 (8)	0.0244 (6)	0.0107 (7)	0.0006 (6)	−0.0009 (6)
O3	0.0665 (9)	0.0457 (9)	0.0357 (7)	−0.0255 (7)	0.0061 (6)	0.0041 (6)
O4	0.0820 (10)	0.0388 (7)	0.0255 (6)	−0.0119 (7)	0.0105 (6)	−0.0018 (5)
O6	0.0593 (8)	0.0361 (7)	0.0345 (6)	−0.0074 (6)	0.0152 (6)	−0.0019 (5)
S1	0.0406 (2)	0.0300 (2)	0.02406 (18)	0.00257 (18)	0.00257 (14)	0.00307 (17)

C1—C2	1.382 (3)	C7—H7	0.9800
C1—C6	1.386 (3)	C8—O3	1.195 (2)
C1—S1	1.7596 (18)	C8—O4	1.314 (2)
C2—C3	1.390 (3)	C9—C10	1.499 (2)
C2—H2	0.9300	C9—H9A	0.9700
C3—C4	1.370 (3)	C9—H9B	0.9700
C3—H3	0.9300	C10—O6	1.226 (2)
C4—C5	1.378 (3)	C10—N2	1.320 (2)
C4—H4	0.9300	N1—S1	1.6289 (15)
C5—C6	1.377 (3)	N1—H1B	0.77 (2)
C5—H5	0.9300	N2—H1A	0.88 (4)
C6—H6	0.9300	N2—H2A	0.95 (3)
C7—N1	1.460 (2)	O1—S1	1.4319 (14)
C7—C8	1.523 (2)	O2—S1	1.4304 (14)
C7—C9	1.542 (2)	O4—H4A	0.8200
C2—C1—C6	121.60 (18)	O3—C8—C7	124.44 (15)
C2—C1—S1	119.45 (14)	O4—C8—C7	109.93 (14)
C6—C1—S1	118.76 (14)	C10—C9—C7	111.80 (14)
C1—C2—C3	118.21 (19)	C10—C9—H9A	109.3
C1—C2—H2	120.9	C7—C9—H9A	109.3
C3—C2—H2	120.9	C10—C9—H9B	109.3
C4—C3—C2	120.39 (19)	C7—C9—H9B	109.3
C4—C3—H3	119.8	H9A—C9—H9B	107.9
C2—C3—H3	119.8	O6—C10—N2	120.99 (18)
C3—C4—C5	120.86 (19)	O6—C10—C9	120.76 (16)
C3—C4—H4	119.6	N2—C10—C9	118.24 (18)
C5—C4—H4	119.6	C7—N1—S1	120.55 (12)
C6—C5—C4	119.82 (19)	C7—N1—H1B	116.2 (14)
C6—C5—H5	120.1	S1—N1—H1B	110.9 (14)
C4—C5—H5	120.1	C10—N2—H1A	113.9 (19)
C5—C6—C1	119.11 (18)	C10—N2—H2A	117.8 (19)
C5—C6—H6	120.4	H1A—N2—H2A	127 (3)
C1—C6—H6	120.4	C8—O4—H4A	109.5
N1—C7—C8	112.54 (13)	O2—S1—O1	119.35 (9)
N1—C7—C9	108.73 (13)	O2—S1—N1	105.46 (8)
C8—C7—C9	107.92 (13)	O1—S1—N1	106.44 (8)
N1—C7—H7	109.2	O2—S1—C1	108.01 (9)
C8—C7—H7	109.2	O1—S1—C1	109.25 (8)
C9—C7—H7	109.2	N1—S1—C1	107.77 (8)
O3—C8—O4	125.58 (16)
C6—C1—C2—C3	−0.1 (3)	C7—C9—C10—O6	−79.6 (2)
S1—C1—C2—C3	174.80 (16)	C7—C9—C10—N2	100.7 (2)
C1—C2—C3—C4	−0.6 (3)	C8—C7—N1—S1	−99.21 (15)
C2—C3—C4—C5	0.9 (3)	C9—C7—N1—S1	141.28 (13)
C3—C4—C5—C6	−0.6 (3)	C7—N1—S1—O2	−168.94 (12)
C4—C5—C6—C1	−0.1 (3)	C7—N1—S1—O1	−41.22 (15)
C2—C1—C6—C5	0.5 (3)	C7—N1—S1—C1	75.87 (14)
S1—C1—C6—C5	−174.49 (16)	C2—C1—S1—O2	160.50 (14)
N1—C7—C8—O3	−21.2 (2)	C6—C1—S1—O2	−24.43 (17)
C9—C7—C8—O3	98.8 (2)	C2—C1—S1—O1	29.25 (17)
N1—C7—C8—O4	161.31 (14)	C6—C1—S1—O1	−155.68 (14)
C9—C7—C8—O4	−78.71 (17)	C2—C1—S1—N1	−86.01 (16)
N1—C7—C9—C10	−78.10 (18)	C6—C1—S1—N1	89.06 (15)
C8—C7—C9—C10	159.55 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1i	0.77 (2)	2.31 (2)	3.076 (2)	168.6 (19)
N2—H2A···O2ii	0.95 (3)	2.06 (3)	2.998 (3)	172 (3)
O4—H4A···O6iii	0.82	1.82	2.5804 (18)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1i	0.77 (2)	2.31 (2)	3.076 (2)	168.6 (19)
N2—H2A⋯O2ii	0.95 (3)	2.06 (3)	2.998 (3)	172 (3)
O4—H4A⋯O6iii	0.82	1.82	2.5804 (18)	155

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