4-Methyl-2-(2-nitro-benzene-sulfon-amido)-penta-noic acid.

In the title compound, C(12)H(16)N(2)O(6)S, the S atom adopts a distorted tetra-hedral geometry with an O-S-O angle of 119.76 (13)°. The nitro group is twisted by 35.34 (2)° with respect to the aromatic ring; it accepts an N-H⋯O hydrogen bond, resulting in a S(7) motif. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds connect the mol-ecules into an infinite chain along the a axis. The methyl C atoms of the isopropyl group are disordered in a 1:1 ratio.

Related literature

For a related structure, see: Arshad et al. (2010 ▶), For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H16N2O6S

M = 316.33

Orthorhombic,

a = 6.9593 (5) Å

b = 10.7560 (8) Å

c = 20.8431 (14) Å

V = 1560.19 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.45 × 0.38 × 0.29 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.902, T max = 0.935

11203 measured reflections

2730 independent reflections

2029 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.090

S = 0.99

2730 reflections

212 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1117 Friedel pairs

Flack parameter: 0.07 (10)

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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033260/ng5283sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033260/ng5283Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812033260/ng5283Isup3.cml

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

C12H16N2O6S	F(000) = 664
Mr = 316.33	Dx = 1.347 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1789 reflections
a = 6.9593 (5) Å	θ = 2.7–19.5°
b = 10.7560 (8) Å	µ = 0.23 mm−1
c = 20.8431 (14) Å	T = 296 K
V = 1560.19 (19) Å3	Prismatic, colorless
Z = 4	0.45 × 0.38 × 0.29 mm

Bruker Kappa APEXII CCD diffractometer	2730 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
Tmin = 0.902, Tmax = 0.935	k = −12→12
11203 measured reflections	l = −24→24

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.041P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
2730 reflections	Δρmax = 0.15 e Å−3
212 parameters	Δρmin = −0.20 e Å−3
10 restraints	Absolute structure: Flack (1983), 1117 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.07 (10)

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	Occ. (<1)
S1	0.85210 (10)	0.49317 (7)	0.11950 (3)	0.0477 (2)
O1	0.6834 (3)	0.8270 (3)	0.21732 (13)	0.0947 (9)
N1	0.7618 (4)	0.7669 (3)	0.17531 (14)	0.0577 (7)
C1	1.0039 (4)	0.5944 (3)	0.16432 (12)	0.0445 (7)
O2	0.6943 (3)	0.7525 (2)	0.12226 (12)	0.0783 (7)
N2	0.8391 (4)	0.5420 (2)	0.04664 (11)	0.0433 (6)
C2	0.9481 (4)	0.7099 (3)	0.18997 (13)	0.0460 (8)
O3	0.6652 (3)	0.5002 (2)	0.14685 (10)	0.0691 (6)
C3	1.0679 (5)	0.7759 (3)	0.22962 (15)	0.0663 (10)
H3	1.0269	0.8509	0.2471	0.080*
O4	0.9507 (3)	0.37724 (17)	0.11794 (10)	0.0633 (6)
C4	1.2476 (5)	0.7316 (4)	0.24342 (17)	0.0794 (12)
H4	1.3294	0.7770	0.2698	0.095*
O5	1.1024 (3)	0.73707 (19)	0.01558 (9)	0.0505 (6)
C5	1.3060 (5)	0.6211 (4)	0.21847 (17)	0.0757 (11)
H5	1.4283	0.5913	0.2278	0.091*
O6	1.3184 (3)	0.5923 (2)	−0.00802 (12)	0.0610 (6)
C6	1.1854 (5)	0.5525 (3)	0.17923 (14)	0.0569 (9)
H6	1.2276	0.4769	0.1627	0.068*
C12	1.1431 (4)	0.6294 (3)	0.00506 (12)	0.0429 (7)
C7A	1.0001 (4)	0.5234 (2)	0.00245 (13)	0.0401 (7)	0.50
H7A	1.0676	0.4480	0.0161	0.048*	0.50
C8A	0.938 (3)	0.504 (2)	−0.0676 (7)	0.046 (3)	0.50
H81	0.8773	0.5793	−0.0830	0.056*	0.50
H82	1.0510	0.4890	−0.0936	0.056*	0.50
C9A	0.798 (5)	0.395 (3)	−0.0769 (14)	0.0651 (12)	0.50
H9A	0.7104	0.3945	−0.0400	0.078*	0.50
C10A	0.676 (4)	0.413 (4)	−0.1372 (12)	0.104 (7)	0.50
H10A	0.5886	0.4815	−0.1308	0.156*	0.50
H10B	0.6040	0.3390	−0.1457	0.156*	0.50
H10C	0.7580	0.4312	−0.1730	0.156*	0.50
C11A	0.903 (9)	0.272 (3)	−0.077 (3)	0.116 (7)	0.50
H11A	0.9924	0.2710	−0.1126	0.174*	0.50
H11B	0.8124	0.2058	−0.0824	0.174*	0.50
H11C	0.9716	0.2622	−0.0378	0.174*	0.50
C7B	1.0001 (4)	0.5234 (2)	0.00245 (13)	0.0401 (7)	0.50
H7B	1.0645	0.4444	0.0117	0.048*	0.50
C8B	0.910 (4)	0.520 (2)	−0.0647 (7)	0.046 (3)	0.50
H83	0.8243	0.5907	−0.0693	0.056*	0.50
H84	1.0109	0.5285	−0.0964	0.056*	0.50
C9B	0.797 (5)	0.401 (3)	−0.0783 (13)	0.0651 (12)	0.50
H9B	0.6792	0.4034	−0.0527	0.078*	0.50
C10B	0.739 (4)	0.398 (4)	−0.1495 (12)	0.104 (7)	0.50
H10D	0.6714	0.4726	−0.1601	0.156*	0.50
H10E	0.6568	0.3273	−0.1570	0.156*	0.50
H10F	0.8518	0.3907	−0.1756	0.156*	0.50
C11B	0.905 (9)	0.283 (3)	−0.061 (3)	0.116 (7)	0.50
H11D	1.0278	0.2832	−0.0812	0.174*	0.50
H11E	0.8321	0.2123	−0.0743	0.174*	0.50
H11F	0.9217	0.2803	−0.0149	0.174*	0.50
H2N	0.780 (5)	0.611 (2)	0.042 (2)	0.139*
H6O	1.393 (6)	0.655 (3)	−0.013 (3)	0.174*

	U11	U22	U33	U12	U13	U23
S1	0.0575 (4)	0.0422 (4)	0.0435 (4)	−0.0031 (4)	0.0088 (4)	0.0032 (4)
O1	0.0808 (18)	0.107 (2)	0.096 (2)	0.0244 (16)	0.0092 (15)	−0.0496 (17)
N1	0.0688 (18)	0.0496 (18)	0.0548 (19)	0.0067 (14)	0.0099 (16)	−0.0070 (15)
C1	0.0542 (19)	0.0466 (19)	0.0328 (16)	0.0021 (16)	0.0081 (14)	0.0022 (14)
O2	0.0921 (16)	0.0889 (18)	0.0541 (14)	0.0387 (14)	−0.0074 (14)	0.0009 (14)
N2	0.0490 (14)	0.0458 (15)	0.0351 (13)	0.0012 (11)	0.0038 (12)	−0.0004 (11)
C2	0.0512 (17)	0.052 (2)	0.0349 (16)	0.0026 (16)	0.0075 (14)	0.0006 (15)
O3	0.0682 (14)	0.0802 (16)	0.0589 (13)	−0.0165 (15)	0.0231 (11)	−0.0023 (12)
C3	0.075 (2)	0.068 (2)	0.055 (2)	−0.004 (2)	0.0129 (18)	−0.019 (2)
O4	0.0946 (16)	0.0380 (13)	0.0574 (13)	0.0074 (10)	0.0061 (13)	0.0052 (11)
C4	0.062 (2)	0.106 (3)	0.070 (3)	−0.012 (2)	0.005 (2)	−0.034 (2)
O5	0.0464 (11)	0.0390 (13)	0.0661 (15)	−0.0011 (9)	0.0019 (10)	−0.0059 (11)
C5	0.058 (2)	0.108 (3)	0.061 (2)	0.012 (2)	−0.0014 (18)	−0.014 (2)
O6	0.0413 (13)	0.0466 (13)	0.0952 (17)	0.0033 (10)	0.0060 (12)	−0.0068 (13)
C6	0.058 (2)	0.071 (2)	0.0417 (18)	0.0103 (17)	0.0038 (16)	−0.0035 (16)
C12	0.0466 (16)	0.0431 (19)	0.0391 (17)	0.0025 (14)	−0.0021 (15)	−0.0025 (14)
C7A	0.0409 (15)	0.0398 (17)	0.0396 (15)	−0.0010 (13)	0.0078 (12)	−0.0005 (14)
C8A	0.053 (5)	0.042 (5)	0.044 (2)	−0.005 (4)	0.008 (3)	−0.009 (2)
C9A	0.085 (2)	0.058 (3)	0.052 (2)	−0.029 (2)	−0.0011 (19)	−0.007 (2)
C10A	0.143 (16)	0.115 (10)	0.055 (9)	−0.066 (13)	−0.013 (10)	−0.011 (6)
C11A	0.146 (4)	0.049 (5)	0.15 (2)	−0.017 (5)	−0.031 (13)	−0.046 (7)
C7B	0.0409 (15)	0.0398 (17)	0.0396 (15)	−0.0010 (13)	0.0078 (12)	−0.0005 (14)
C8B	0.053 (5)	0.042 (5)	0.044 (2)	−0.005 (4)	0.008 (3)	−0.009 (2)
C9B	0.085 (2)	0.058 (3)	0.052 (2)	−0.029 (2)	−0.0011 (19)	−0.007 (2)
C10B	0.143 (16)	0.115 (10)	0.055 (9)	−0.066 (13)	−0.013 (10)	−0.011 (6)
C11B	0.146 (4)	0.049 (5)	0.15 (2)	−0.017 (5)	−0.031 (13)	−0.046 (7)

S1—O3	1.422 (2)	C8A—C9A	1.532 (12)
S1—O4	1.424 (2)	C8A—H81	0.9700
S1—N2	1.609 (2)	C8A—H82	0.9700
S1—C1	1.781 (3)	C9A—C11A	1.511 (13)
O1—N1	1.217 (3)	C9A—C10A	1.531 (13)
N1—O2	1.211 (3)	C9A—H9A	0.9800
N1—C2	1.466 (4)	C10A—H10A	0.9600
C1—C6	1.376 (4)	C10A—H10B	0.9600
C1—C2	1.408 (4)	C10A—H10C	0.9600
N2—C7A	1.464 (3)	C11A—H11A	0.9600
N2—H2N	0.850 (10)	C11A—H11B	0.9600
C2—C3	1.372 (4)	C11A—H11C	0.9600
C3—C4	1.369 (5)	C8B—C9B	1.530 (11)
C3—H3	0.9300	C8B—H83	0.9700
C4—C5	1.360 (5)	C8B—H84	0.9700
C4—H4	0.9300	C9B—C11B	1.513 (12)
O5—C12	1.212 (3)	C9B—C10B	1.538 (14)
C5—C6	1.385 (4)	C9B—H9B	0.9800
C5—H5	0.9300	C10B—H10D	0.9600
O6—C12	1.312 (3)	C10B—H10E	0.9600
O6—H6O	0.852 (10)	C10B—H10F	0.9600
C6—H6	0.9300	C11B—H11D	0.9600
C12—C7A	1.514 (4)	C11B—H11E	0.9600
C7A—C8A	1.538 (11)	C11B—H11F	0.9600
C7A—H7A	0.9800
O3—S1—O4	119.76 (13)	N2—C7A—H7A	107.3
O3—S1—N2	108.02 (13)	C12—C7A—H7A	107.3
O4—S1—N2	106.94 (13)	C8A—C7A—H7A	107.3
O3—S1—C1	107.46 (13)	C9A—C8A—C7A	113.8 (14)
O4—S1—C1	105.15 (14)	C9A—C8A—H81	108.8
N2—S1—C1	109.20 (13)	C7A—C8A—H81	108.8
O2—N1—O1	123.4 (3)	C9A—C8A—H82	108.8
O2—N1—C2	118.7 (3)	C7A—C8A—H82	108.8
O1—N1—C2	118.0 (3)	H81—C8A—H82	107.7
C6—C1—C2	117.2 (3)	C11A—C9A—C10A	112.0 (15)
C6—C1—S1	117.6 (2)	C11A—C9A—C8A	111.0 (17)
C2—C1—S1	125.1 (2)	C10A—C9A—C8A	111.0 (15)
C7A—N2—S1	120.39 (19)	C11A—C9A—H9A	107.5
C7A—N2—H2N	115 (3)	C10A—C9A—H9A	107.5
S1—N2—H2N	114 (3)	C8A—C9A—H9A	107.5
C3—C2—C1	121.2 (3)	C9B—C8B—H83	108.9
C3—C2—N1	116.5 (3)	C9B—C8B—H84	108.9
C1—C2—N1	122.3 (3)	H83—C8B—H84	107.7
C4—C3—C2	120.1 (3)	C11B—C9B—C8B	113.7 (15)
C4—C3—H3	120.0	C11B—C9B—C10B	110.3 (16)
C2—C3—H3	120.0	C8B—C9B—C10B	109.5 (16)
C5—C4—C3	119.8 (4)	C11B—C9B—H9B	107.7
C5—C4—H4	120.1	C8B—C9B—H9B	107.7
C3—C4—H4	120.1	C10B—C9B—H9B	107.7
C4—C5—C6	120.7 (3)	C9B—C10B—H10D	109.5
C4—C5—H5	119.7	C9B—C10B—H10E	109.5
C6—C5—H5	119.7	H10D—C10B—H10E	109.5
C12—O6—H6O	111 (4)	C9B—C10B—H10F	109.5
C1—C6—C5	121.0 (3)	H10D—C10B—H10F	109.5
C1—C6—H6	119.5	H10E—C10B—H10F	109.5
C5—C6—H6	119.5	C9B—C11B—H11D	109.5
O5—C12—O6	123.0 (3)	C9B—C11B—H11E	109.5
O5—C12—C7A	124.9 (3)	H11D—C11B—H11E	109.5
O6—C12—C7A	112.0 (2)	C9B—C11B—H11F	109.5
N2—C7A—C12	112.2 (2)	H11D—C11B—H11F	109.5
N2—C7A—C8A	113.6 (10)	H11E—C11B—H11F	109.5
C12—C7A—C8A	108.9 (9)
O3—S1—C1—C6	137.9 (2)	C1—C2—C3—C4	1.9 (5)
O4—S1—C1—C6	9.3 (3)	N1—C2—C3—C4	−177.2 (3)
N2—S1—C1—C6	−105.2 (2)	C2—C3—C4—C5	−0.9 (5)
O3—S1—C1—C2	−36.9 (3)	C3—C4—C5—C6	−0.1 (5)
O4—S1—C1—C2	−165.5 (2)	C2—C1—C6—C5	0.7 (4)
N2—S1—C1—C2	80.0 (3)	S1—C1—C6—C5	−174.5 (2)
O3—S1—N2—C7A	−168.2 (2)	C4—C5—C6—C1	0.2 (5)
O4—S1—N2—C7A	−38.0 (2)	S1—N2—C7A—C12	−88.8 (2)
C1—S1—N2—C7A	75.3 (2)	S1—N2—C7A—C8A	147.2 (10)
C6—C1—C2—C3	−1.8 (4)	O5—C12—C7A—N2	−32.7 (4)
S1—C1—C2—C3	173.0 (2)	O6—C12—C7A—N2	149.8 (2)
C6—C1—C2—N1	177.3 (3)	O5—C12—C7A—C8A	93.8 (11)
S1—C1—C2—N1	−7.9 (4)	O6—C12—C7A—C8A	−83.6 (11)
O2—N1—C2—C3	144.3 (3)	N2—C7A—C8A—C9A	−56 (2)
O1—N1—C2—C3	−35.4 (4)	C12—C7A—C8A—C9A	177.8 (18)
O2—N1—C2—C1	−34.8 (4)	C7A—C8A—C9A—C11A	−80 (3)
O1—N1—C2—C1	145.5 (3)	C7A—C8A—C9A—C10A	155 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O2	0.85 (1)	2.34 (4)	2.937 (3)	128 (4)
O6—H6O···O5i	0.85 (1)	1.87 (2)	2.702 (3)	166 (5)
N2—H2N···O5ii	0.85 (1)	2.38 (2)	3.169 (3)	155 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O2	0.85 (1)	2.34 (4)	2.937 (3)	128 (4)
O6—H6O⋯O5i	0.85 (1)	1.87 (2)	2.702 (3)	166 (5)
N2—H2N⋯O5ii	0.85 (1)	2.38 (2)	3.169 (3)	155 (4)

Symmetry codes: (i) ; (ii) .