(2S)-3-Carbamoyl-2-(4-meth-oxy-benzene-sulfonamido)-propanoic acid.

In the title compound, C(11)H(14)N(2)O(6)S, an amino acid-derived sulfonamide, the acetamido group and the carb-oxy-lic group are oriented at dihedral angles of 45.84 (5)° and 47.97 (5)° respectively, with respect to the aromatic ring. In the crystal, the mol-ecules are connected by N-H⋯O and O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For related structures, see: Arshad et al. (2009a ▶,b ▶), Khan et al. (2009 ▶). Amino acid-derived sulfonamide derivatives have been used as potent inhibitors of Procollagen C-Proteinase, see: Dankwardt et al. (2002 ▶).

Experimental

Crystal data

C11H14N2O6S

M = 302.30

Monoclinic,

a = 7.1462 (1) Å

b = 8.9874 (2) Å

c = 11.1418 (2) Å

β = 108.090 (1)°

V = 680.22 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.42 × 0.26 × 0.23 mm

Data collection

Siemens SMART diffractometer equipped with a Bruker APEXII detector

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.897, T max = 0.942

15356 measured reflections

3434 independent reflections

3335 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.063

S = 1.04

3434 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1581 Friedel pairs

Flack parameter: −0.01 (4)

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 (Farrugia, 1997 ▶), PLATON (Spek, 2009 ▶) and X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681003607X/hb5624sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003607X/hb5624Isup2.hkl

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

C11H14N2O6S	F(000) = 316
Mr = 302.30	Dx = 1.476 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8744 reflections
a = 7.1462 (1) Å	θ = 3.0–28.6°
b = 8.9874 (2) Å	µ = 0.27 mm−1
c = 11.1418 (2) Å	T = 100 K
β = 108.090 (1)°	Needle, colorless
V = 680.22 (2) Å3	0.42 × 0.26 × 0.23 mm
Z = 2

Siemens SMART diffractometer equipped with a Bruker APEXII detector	3434 independent reflections
Radiation source: fine-focus sealed tube	3335 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 28.6°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→9
Tmin = 0.897, Tmax = 0.942	k = −11→12
15356 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)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.063	w = 1/[σ2(Fo2) + (0.0368P)2 + 0.1181P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3434 reflections	Δρmax = 0.30 e Å−3
194 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 1581 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (4)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.29092 (4)	−0.00600 (3)	0.24767 (3)	0.01463 (7)
O1	−0.42282 (14)	0.05232 (12)	0.31015 (9)	0.0222 (2)
N1	−0.30244 (16)	0.10725 (12)	0.13389 (10)	0.0151 (2)
C1	−0.04937 (16)	−0.00385 (17)	0.35229 (10)	0.0149 (2)
H1N	−0.375 (3)	0.193 (2)	0.1302 (16)	0.018*
H1N2	−0.739 (3)	−0.027 (2)	−0.1489 (16)	0.018*
O2	−0.32080 (14)	−0.15497 (11)	0.19714 (9)	0.0228 (2)
N2	−0.65042 (16)	0.03205 (13)	−0.13841 (11)	0.0173 (2)
C2	0.08556 (19)	−0.11149 (14)	0.34294 (12)	0.0168 (2)
H2	0.0478	−0.1847	0.2784	0.020*
H2N2	−0.669 (2)	0.130 (2)	−0.1430 (17)	0.020*
O3	−0.03178 (13)	0.32670 (11)	0.13252 (9)	0.0204 (2)
C3	0.27541 (19)	−0.11253 (15)	0.42761 (13)	0.0181 (2)
H3	0.3675	−0.1859	0.4212	0.022*
O4	0.12194 (15)	0.17646 (12)	0.03322 (11)	0.0241 (2)
C4	0.32887 (17)	−0.00447 (18)	0.52207 (11)	0.0173 (2)
H4O	0.208 (3)	0.238 (2)	0.0560 (19)	0.026*
O5	−0.42990 (13)	−0.15430 (10)	−0.10103 (9)	0.01674 (18)
C5	0.1919 (2)	0.10294 (16)	0.53159 (12)	0.0196 (3)
H5	0.2285	0.1754	0.5968	0.024*
O6	0.51004 (13)	0.00661 (13)	0.60857 (8)	0.0223 (2)
C6	0.0043 (2)	0.10393 (16)	0.44689 (12)	0.0189 (2)
H6	−0.0877	0.1776	0.4529	0.023*
C7	−0.17978 (17)	0.09007 (14)	0.05256 (11)	0.0132 (2)
H7	−0.1132	−0.0091	0.0698	0.016*
C8	−0.02147 (17)	0.21146 (14)	0.07875 (12)	0.0139 (2)
C9	−0.30540 (17)	0.09626 (14)	−0.08778 (11)	0.0138 (2)
H9A	−0.3628	0.1968	−0.1088	0.017*
H9B	−0.2219	0.0752	−0.1420	0.017*
C10	−0.46823 (16)	−0.01830 (16)	−0.11135 (10)	0.0134 (2)
C11	0.6510 (2)	−0.10641 (19)	0.60538 (14)	0.0249 (3)
H11A	0.5988	−0.2044	0.6167	0.037*
H11B	0.7742	−0.0886	0.6734	0.037*
H11C	0.6762	−0.1032	0.5238	0.037*

	U11	U22	U33	U12	U13	U23
S1	0.01351 (12)	0.01393 (13)	0.01602 (13)	−0.00161 (11)	0.00396 (9)	0.00279 (11)
O1	0.0180 (4)	0.0296 (5)	0.0215 (4)	0.0010 (4)	0.0097 (4)	0.0059 (4)
N1	0.0158 (5)	0.0138 (5)	0.0171 (5)	0.0037 (4)	0.0074 (4)	0.0040 (4)
C1	0.0147 (5)	0.0149 (5)	0.0141 (5)	0.0006 (5)	0.0030 (4)	0.0027 (5)
O2	0.0230 (5)	0.0141 (5)	0.0264 (5)	−0.0041 (4)	0.0005 (4)	0.0023 (4)
N2	0.0125 (5)	0.0143 (6)	0.0252 (6)	−0.0011 (4)	0.0061 (4)	0.0012 (4)
C2	0.0199 (6)	0.0143 (6)	0.0167 (6)	−0.0004 (5)	0.0062 (5)	−0.0001 (5)
O3	0.0141 (4)	0.0163 (5)	0.0297 (5)	−0.0005 (3)	0.0053 (4)	−0.0082 (4)
C3	0.0180 (6)	0.0181 (6)	0.0188 (6)	0.0021 (5)	0.0066 (5)	0.0012 (5)
O4	0.0170 (5)	0.0220 (5)	0.0373 (6)	−0.0072 (4)	0.0144 (4)	−0.0125 (4)
C4	0.0161 (5)	0.0203 (6)	0.0149 (5)	0.0006 (5)	0.0040 (4)	0.0033 (6)
O5	0.0131 (4)	0.0122 (4)	0.0244 (4)	−0.0006 (3)	0.0051 (3)	−0.0009 (4)
C5	0.0214 (6)	0.0199 (6)	0.0158 (6)	0.0006 (5)	0.0033 (5)	−0.0032 (5)
O6	0.0168 (4)	0.0290 (5)	0.0180 (4)	0.0028 (4)	0.0009 (3)	−0.0013 (4)
C6	0.0211 (6)	0.0171 (6)	0.0179 (6)	0.0029 (5)	0.0054 (5)	−0.0013 (5)
C7	0.0118 (5)	0.0121 (5)	0.0159 (5)	0.0001 (4)	0.0047 (4)	−0.0003 (4)
C8	0.0108 (5)	0.0143 (6)	0.0148 (5)	0.0006 (4)	0.0012 (4)	−0.0002 (4)
C9	0.0121 (5)	0.0131 (5)	0.0157 (5)	−0.0017 (4)	0.0037 (4)	−0.0002 (5)
C10	0.0135 (5)	0.0139 (6)	0.0128 (5)	−0.0029 (4)	0.0042 (4)	−0.0009 (4)
C11	0.0170 (6)	0.0362 (8)	0.0200 (6)	0.0060 (5)	0.0034 (5)	0.0027 (6)

S1—O1	1.4336 (10)	O4—H4O	0.81 (2)
S1—O2	1.4424 (11)	C4—O6	1.3565 (14)
S1—N1	1.6078 (11)	C4—C5	1.402 (2)
S1—C1	1.7576 (11)	O5—C10	1.2500 (17)
N1—C7	1.4514 (15)	C5—C6	1.3790 (18)
N1—H1N	0.927 (18)	C5—H5	0.9500
C1—C2	1.3924 (18)	O6—C11	1.4389 (18)
C1—C6	1.3948 (18)	C6—H6	0.9500
N2—C10	1.3217 (16)	C7—C8	1.5330 (17)
N2—H1N2	0.812 (19)	C7—C9	1.5435 (16)
N2—H2N2	0.89 (2)	C7—H7	1.0000
C2—C3	1.3914 (18)	C9—C10	1.5144 (17)
C2—H2	0.9500	C9—H9A	0.9900
O3—C8	1.2101 (16)	C9—H9B	0.9900
C3—C4	1.3954 (19)	C11—H11A	0.9800
C3—H3	0.9500	C11—H11B	0.9800
O4—C8	1.3151 (16)	C11—H11C	0.9800
O1—S1—O2	119.27 (6)	C4—O6—C11	116.86 (11)
O1—S1—N1	105.72 (6)	C5—C6—C1	119.57 (12)
O2—S1—N1	108.34 (6)	C5—C6—H6	120.2
O1—S1—C1	109.41 (6)	C1—C6—H6	120.2
O2—S1—C1	105.36 (6)	N1—C7—C8	111.01 (10)
N1—S1—C1	108.38 (6)	N1—C7—C9	110.77 (10)
C7—N1—S1	122.14 (9)	C8—C7—C9	109.26 (10)
C7—N1—H1N	120.1 (11)	N1—C7—H7	108.6
S1—N1—H1N	117.0 (11)	C8—C7—H7	108.6
C2—C1—C6	120.31 (11)	C9—C7—H7	108.6
C2—C1—S1	120.20 (10)	O3—C8—O4	124.77 (12)
C6—C1—S1	119.46 (10)	O3—C8—C7	123.27 (11)
C10—N2—H1N2	118.7 (12)	O4—C8—C7	111.95 (10)
C10—N2—H2N2	118.0 (11)	C10—C9—C7	108.97 (10)
H1N2—N2—H2N2	123.3 (16)	C10—C9—H9A	109.9
C3—C2—C1	120.40 (12)	C7—C9—H9A	109.9
C3—C2—H2	119.8	C10—C9—H9B	109.9
C1—C2—H2	119.8	C7—C9—H9B	109.9
C2—C3—C4	119.19 (12)	H9A—C9—H9B	108.3
C2—C3—H3	120.4	O5—C10—N2	121.87 (12)
C4—C3—H3	120.4	O5—C10—C9	120.94 (10)
C8—O4—H4O	109.0 (14)	N2—C10—C9	117.14 (12)
O6—C4—C3	124.36 (12)	O6—C11—H11A	109.5
O6—C4—C5	115.50 (12)	O6—C11—H11B	109.5
C3—C4—C5	120.14 (11)	H11A—C11—H11B	109.5
C6—C5—C4	120.38 (12)	O6—C11—H11C	109.5
C6—C5—H5	119.8	H11A—C11—H11C	109.5
C4—C5—H5	119.8	H11B—C11—H11C	109.5
O1—S1—N1—C7	176.40 (10)	C3—C4—O6—C11	−3.51 (19)
O2—S1—N1—C7	−54.66 (11)	C5—C4—O6—C11	176.95 (12)
C1—S1—N1—C7	59.18 (11)	C4—C5—C6—C1	0.8 (2)
O1—S1—C1—C2	148.92 (10)	C2—C1—C6—C5	−0.26 (19)
O2—S1—C1—C2	19.54 (12)	S1—C1—C6—C5	177.93 (11)
N1—S1—C1—C2	−96.25 (11)	S1—N1—C7—C8	−108.87 (11)
O1—S1—C1—C6	−29.28 (12)	S1—N1—C7—C9	129.56 (10)
O2—S1—C1—C6	−158.65 (10)	N1—C7—C8—O3	−18.96 (16)
N1—S1—C1—C6	85.55 (11)	C9—C7—C8—O3	103.49 (14)
C6—C1—C2—C3	−0.15 (19)	N1—C7—C8—O4	162.62 (11)
S1—C1—C2—C3	−178.33 (10)	C9—C7—C8—O4	−74.93 (13)
C1—C2—C3—C4	0.06 (19)	N1—C7—C9—C10	−54.36 (13)
C2—C3—C4—O6	−179.08 (12)	C8—C7—C9—C10	−176.96 (10)
C2—C3—C4—C5	0.4 (2)	C7—C9—C10—O5	−65.42 (14)
O6—C4—C5—C6	178.71 (12)	C7—C9—C10—N2	112.13 (12)
C3—C4—C5—C6	−0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O3i	0.812 (19)	2.147 (19)	2.9430 (15)	166.9 (16)
N2—H2N2···O2ii	0.89 (2)	2.02 (2)	2.8808 (16)	162.9 (17)
C11—H11B···O3iii	0.98	2.48	3.3701 (17)	150
N1—H1N···O5ii	0.927 (18)	1.907 (18)	2.8196 (14)	167.8 (16)
O4—H4O···O5iv	0.81 (2)	1.79 (2)	2.5875 (14)	169 (2)
C9—H9A···O2ii	0.99	2.54	3.4055 (16)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O3i	0.812 (19)	2.147 (19)	2.9430 (15)	166.9 (16)
N2—H2N2⋯O2ii	0.89 (2)	2.02 (2)	2.8808 (16)	162.9 (17)
C11—H11B⋯O3iii	0.98	2.48	3.3701 (17)	150
N1—H1N⋯O5ii	0.927 (18)	1.907 (18)	2.8196 (14)	167.8 (16)
O4—H4O⋯O5iv	0.81 (2)	1.79 (2)	2.5875 (14)	169 (2)
C9—H9A⋯O2ii	0.99	2.54	3.4055 (16)	145

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