N-(2,5-Dimethyl-phen-yl)succinamic acid monohydrate.

In the title compound, C(12)H(15)NO(3)·H(2)O, the conformation of the N-H bond in the amide segment is syn to the ortho-methyl group and anti to the meta-methyl group in the benzene ring. Further, the conformations of the amide O and the carbonyl O atom of the acid segment are anti to the adjacent methyl-ene H atoms. The C=O and O-H bonds of the acid group are syn to one another. The structure shows an inter-esting hydrogen-bonding pattern with the water mol-ecule forming hydrogen bonds with three different mol-ecules of the compound. In the crystal, mol-ecules are packed into infinite chains through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For our studies of the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (1999 ▶, 2000 ▶, 2010 ▶); Saraswathi et al. (2011 ▶). For modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Leiserowitz (1976 ▶). For packing of mol­ecules involving dimeric hydrogen-bonding associations of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C12H15NO3·H2O

M = 239.27

Monoclinic,

a = 22.012 (4) Å

b = 6.051 (1) Å

c = 9.558 (2) Å

β = 95.90 (1)°

V = 1266.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.24 × 0.08 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.978, T max = 0.996

4503 measured reflections

2293 independent reflections

964 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.099

wR(F 2) = 0.147

S = 1.08

2293 reflections

168 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024937/sj5169sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024937/sj5169Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024937/sj5169Isup3.cml

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

C12H15NO3·H2O	F(000) = 512
Mr = 239.27	Dx = 1.255 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 663 reflections
a = 22.012 (4) Å	θ = 2.8–27.7°
b = 6.051 (1) Å	µ = 0.09 mm−1
c = 9.558 (2) Å	T = 293 K
β = 95.90 (1)°	Needle, colourless
V = 1266.3 (4) Å3	0.24 × 0.08 × 0.04 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2293 independent reflections
Radiation source: fine-focus sealed tube	964 reflections with I > 2σ(I)
graphite	Rint = 0.075
Rotation method data acquisition using ω scans	θmax = 25.3°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −26→26
Tmin = 0.978, Tmax = 0.996	k = −7→6
4503 measured reflections	l = −11→8

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)] = 0.099	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0275P)2 + 1.0954P] where P = (Fo2 + 2Fc2)/3
2293 reflections	(Δ/σ)max = 0.004
168 parameters	Δρmax = 0.20 e Å−3
4 restraints	Δρmin = −0.22 e Å−3

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	0.1917 (2)	0.0833 (9)	0.5880 (4)	0.0380 (13)
C2	0.1742 (2)	−0.1196 (9)	0.6356 (5)	0.0437 (14)
C3	0.1180 (3)	−0.2041 (9)	0.5786 (5)	0.0550 (15)
H3	0.1049	−0.3402	0.6091	0.066*
C4	0.0817 (2)	−0.0882 (10)	0.4772 (6)	0.0584 (17)
H4	0.0447	−0.1487	0.4400	0.070*
C5	0.0990 (2)	0.1137 (10)	0.4304 (5)	0.0464 (15)
C6	0.1550 (2)	0.2008 (8)	0.4869 (4)	0.0404 (13)
H6	0.1678	0.3377	0.4568	0.048*
C7	0.2891 (2)	0.2840 (9)	0.5756 (4)	0.0392 (13)
C8	0.3462 (2)	0.3619 (9)	0.6640 (4)	0.0439 (14)
H8A	0.3352	0.4145	0.7538	0.053*
H8B	0.3738	0.2377	0.6820	0.053*
C9	0.3788 (2)	0.5434 (8)	0.5942 (5)	0.0474 (14)
H9A	0.3490	0.6525	0.5578	0.057*
H9B	0.4069	0.6156	0.6646	0.057*
C10	0.4137 (2)	0.4669 (10)	0.4765 (5)	0.0387 (13)
C11	0.2134 (2)	−0.2482 (9)	0.7455 (5)	0.0652 (17)
H11A	0.2135	−0.1758	0.8349	0.078*
H11B	0.2544	−0.2560	0.7198	0.078*
H11C	0.1973	−0.3949	0.7518	0.078*
C12	0.0596 (2)	0.2444 (10)	0.3213 (5)	0.0719 (19)
H12A	0.0204	0.1743	0.3034	0.086*
H12B	0.0789	0.2503	0.2358	0.086*
H12C	0.0543	0.3918	0.3553	0.086*
N1	0.24841 (18)	0.1758 (7)	0.6459 (3)	0.0431 (11)
H1N	0.2554 (19)	0.147 (7)	0.733 (2)	0.052*
O1	0.28284 (14)	0.3146 (6)	0.4485 (3)	0.0590 (12)
O2	0.41537 (16)	0.6192 (6)	0.3788 (3)	0.0571 (11)
H2O	0.436 (2)	0.562 (8)	0.321 (4)	0.068*
O3	0.43953 (15)	0.2910 (6)	0.4737 (3)	0.0516 (10)
O4	0.48537 (18)	−0.0138 (6)	0.6831 (4)	0.0569 (11)
H41	0.472 (2)	0.090 (6)	0.631 (4)	0.068*
H42	0.505 (2)	−0.111 (6)	0.647 (5)	0.068*

	U11	U22	U33	U12	U13	U23
C1	0.042 (4)	0.043 (4)	0.031 (3)	−0.007 (3)	0.008 (2)	−0.001 (3)
C2	0.048 (4)	0.045 (4)	0.040 (3)	0.002 (3)	0.012 (3)	−0.002 (3)
C3	0.060 (4)	0.043 (4)	0.066 (4)	−0.009 (4)	0.023 (3)	−0.003 (3)
C4	0.045 (4)	0.066 (5)	0.064 (4)	−0.014 (4)	0.005 (3)	−0.010 (4)
C5	0.036 (3)	0.062 (5)	0.041 (3)	−0.005 (3)	0.002 (3)	−0.006 (3)
C6	0.042 (3)	0.045 (4)	0.034 (3)	−0.003 (3)	0.004 (2)	0.001 (3)
C7	0.034 (3)	0.052 (4)	0.031 (3)	0.003 (3)	0.001 (2)	0.000 (3)
C8	0.035 (3)	0.067 (4)	0.030 (2)	0.001 (3)	0.002 (2)	−0.003 (3)
C9	0.044 (3)	0.057 (4)	0.041 (3)	−0.005 (3)	0.008 (2)	−0.008 (3)
C10	0.030 (3)	0.054 (4)	0.030 (3)	−0.005 (3)	−0.004 (2)	0.001 (3)
C11	0.068 (4)	0.059 (4)	0.071 (4)	0.011 (4)	0.017 (3)	0.012 (3)
C12	0.042 (4)	0.109 (5)	0.062 (3)	−0.010 (4)	−0.006 (3)	0.003 (4)
N1	0.045 (3)	0.057 (3)	0.028 (2)	−0.011 (3)	0.003 (2)	0.009 (2)
O1	0.048 (2)	0.104 (3)	0.0241 (17)	−0.010 (2)	0.0010 (14)	0.005 (2)
O2	0.066 (3)	0.058 (3)	0.051 (2)	0.009 (2)	0.0200 (18)	0.010 (2)
O3	0.055 (2)	0.056 (3)	0.045 (2)	0.012 (2)	0.0104 (17)	0.005 (2)
O4	0.069 (3)	0.056 (3)	0.048 (2)	0.015 (2)	0.019 (2)	0.0068 (19)

C1—C2	1.378 (6)	C8—H8B	0.9700
C1—C6	1.389 (6)	C9—C10	1.499 (6)
C1—N1	1.427 (6)	C9—H9A	0.9700
C2—C3	1.396 (7)	C9—H9B	0.9700
C2—C11	1.506 (6)	C10—O3	1.208 (6)
C3—C4	1.382 (7)	C10—O2	1.315 (6)
C3—H3	0.9300	C11—H11A	0.9600
C4—C5	1.368 (7)	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C5—C6	1.397 (6)	C12—H12A	0.9600
C5—C12	1.511 (6)	C12—H12B	0.9600
C6—H6	0.9300	C12—H12C	0.9600
C7—O1	1.223 (4)	N1—H1N	0.852 (18)
C7—N1	1.344 (5)	O2—H2O	0.830 (19)
C7—C8	1.516 (6)	O4—H41	0.836 (19)
C8—C9	1.504 (6)	O4—H42	0.827 (19)
C8—H8A	0.9700
C2—C1—C6	121.6 (5)	C10—C9—C8	114.3 (4)
C2—C1—N1	119.0 (5)	C10—C9—H9A	108.7
C6—C1—N1	119.5 (5)	C8—C9—H9A	108.7
C1—C2—C3	117.6 (5)	C10—C9—H9B	108.7
C1—C2—C11	122.1 (5)	C8—C9—H9B	108.7
C3—C2—C11	120.3 (5)	H9A—C9—H9B	107.6
C4—C3—C2	120.9 (5)	O3—C10—O2	123.6 (5)
C4—C3—H3	119.6	O3—C10—C9	124.5 (5)
C2—C3—H3	119.6	O2—C10—C9	111.8 (5)
C5—C4—C3	121.5 (5)	C2—C11—H11A	109.5
C5—C4—H4	119.3	C2—C11—H11B	109.5
C3—C4—H4	119.3	H11A—C11—H11B	109.5
C4—C5—C6	118.3 (5)	C2—C11—H11C	109.5
C4—C5—C12	122.3 (5)	H11A—C11—H11C	109.5
C6—C5—C12	119.4 (5)	H11B—C11—H11C	109.5
C1—C6—C5	120.1 (5)	C5—C12—H12A	109.5
C1—C6—H6	119.9	C5—C12—H12B	109.5
C5—C6—H6	119.9	H12A—C12—H12B	109.5
O1—C7—N1	123.9 (4)	C5—C12—H12C	109.5
O1—C7—C8	120.6 (4)	H12A—C12—H12C	109.5
N1—C7—C8	115.5 (4)	H12B—C12—H12C	109.5
C9—C8—C7	112.7 (4)	C7—N1—C1	126.8 (4)
C9—C8—H8A	109.1	C7—N1—H1N	122 (3)
C7—C8—H8A	109.1	C1—N1—H1N	111 (3)
C9—C8—H8B	109.1	C10—O2—H2O	104 (4)
C7—C8—H8B	109.1	H41—O4—H42	117 (5)
H8A—C8—H8B	107.8
C6—C1—C2—C3	0.1 (7)	C4—C5—C6—C1	0.0 (7)
N1—C1—C2—C3	179.0 (4)	C12—C5—C6—C1	179.6 (4)
C6—C1—C2—C11	−179.8 (4)	O1—C7—C8—C9	21.9 (7)
N1—C1—C2—C11	−0.9 (7)	N1—C7—C8—C9	−160.2 (4)
C1—C2—C3—C4	0.4 (7)	C7—C8—C9—C10	−75.3 (5)
C11—C2—C3—C4	−179.7 (4)	C8—C9—C10—O3	−34.4 (7)
C2—C3—C4—C5	−0.7 (8)	C8—C9—C10—O2	148.7 (4)
C3—C4—C5—C6	0.5 (7)	O1—C7—N1—C1	−1.3 (8)
C3—C4—C5—C12	−179.1 (5)	C8—C7—N1—C1	−179.1 (5)
C2—C1—C6—C5	−0.3 (7)	C2—C1—N1—C7	139.5 (5)
N1—C1—C6—C5	−179.2 (4)	C6—C1—N1—C7	−41.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (2)	2.10 (2)	2.914 (4)	161 (4)
O2—H2O···O4ii	0.83 (2)	1.81 (2)	2.621 (5)	164 (5)
O4—H41···O3	0.84 (2)	2.01 (2)	2.831 (5)	168 (5)
O4—H42···O3iii	0.83 (2)	2.07 (2)	2.882 (5)	166 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (2)	2.10 (2)	2.914 (4)	161 (4)
O2—H2O⋯O4ii	0.83 (2)	1.81 (2)	2.621 (5)	164 (5)
O4—H41⋯O3	0.84 (2)	2.01 (2)	2.831 (5)	168 (5)
O4—H42⋯O3iii	0.83 (2)	2.07 (2)	2.882 (5)	166 (5)

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