N,N'-Bis(3-methyl-phen-yl)succinamide dihydrate.

The asymmetric unit of the title compound, C(18)H(20)N(2)O(2)·2H(2)O, contains half a mol-ecule with a center of symmetry at the mid-point of the central C-C bond. The N-H bonds in the amide fragments are anti to the meta-methyl groups in the adjacent benzene rings. The dihedral angle between the benzene ring and the NH-C(O)-CH(2) segment in the two halves of the mol-ecule is 5.6 (4)°. In the crystal, the packing of mol-ecules through O-H⋯O and N-H⋯O hydrogen-bonding inter-actions leads to the formation of layers parallel to the bc plane. The methyl group is disordered with respect to the 3- and 5-positions of the benzene ring, with site-occupation factors of 0.910 (8) and 0.090 (8).

Related literature

For the study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶); Saraswathi et al. (2011a ▶,b ▶). For the effect of substituents on the structures of N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007 ▶). For similar structures, see: Pierrot et al. (1984 ▶).

Experimental

Crystal data

C18H20N2O2·2H2O

M = 332.39

Monoclinic,

a = 13.401 (4) Å

b = 4.937 (2) Å

c = 14.446 (4) Å

β = 108.67 (3)°

V = 905.5 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.48 × 0.12 × 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 = 0.960, T max = 0.997

2857 measured reflections

1679 independent reflections

797 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.126

wR(F 2) = 0.159

S = 1.23

1679 reflections

123 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.23 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/S1600536811020940/wm2494sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020940/wm2494Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020940/wm2494Isup3.cml

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

C18H20N2O2·2H2O	F(000) = 356
Mr = 332.39	Dx = 1.219 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 433 reflections
a = 13.401 (4) Å	θ = 2.9–28.2°
b = 4.937 (2) Å	µ = 0.09 mm−1
c = 14.446 (4) Å	T = 293 K
β = 108.67 (3)°	Needle, colourless
V = 905.5 (5) Å3	0.48 × 0.12 × 0.04 mm
Z = 2

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	1679 independent reflections
Radiation source: fine-focus sealed tube	797 reflections with I > 2σ(I)
graphite	Rint = 0.064
Rotation method data acquisition using ω scans	θmax = 25.7°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→16
Tmin = 0.960, Tmax = 0.997	k = −6→4
2857 measured reflections	l = −17→17

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)] = 0.126	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.23	w = 1/[σ2(Fo2) + (0.P)2 + 1.5559P] where P = (Fo2 + 2Fc2)/3
1679 reflections	(Δ/σ)max = 0.008
123 parameters	Δρmax = 0.23 e Å−3
10 restraints	Δρmin = −0.23 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	Occ. (<1)
O1	0.1286 (3)	0.1598 (8)	0.4781 (2)	0.0590 (12)
N1	0.1521 (3)	0.1149 (9)	0.6385 (3)	0.0471 (13)
H1N	0.1313	0.1791	0.6846	0.056*
C1	0.2292 (4)	−0.0896 (12)	0.6675 (4)	0.0467 (15)
C2	0.2784 (4)	−0.2019 (13)	0.6062 (4)	0.0582 (17)
H2	0.2614	−0.1412	0.5421	0.070*
C3	0.3535 (5)	−0.4063 (13)	0.6396 (6)	0.0668 (19)
C4	0.3776 (5)	−0.4944 (14)	0.7340 (6)	0.076 (2)
H4	0.4281	−0.6288	0.7572	0.091*
C5	0.3280 (5)	−0.3861 (15)	0.7938 (6)	0.081 (2)
H5	0.3439	−0.4510	0.8574	0.098*
C6	0.2547 (5)	−0.1828 (13)	0.7627 (4)	0.0625 (18)
H6	0.2226	−0.1086	0.8051	0.075*
C7	0.1061 (4)	0.2251 (11)	0.5504 (4)	0.0408 (14)
C8	0.0227 (4)	0.4323 (11)	0.5484 (3)	0.0407 (14)
H8A	−0.0337	0.3441	0.5655	0.049*
H8B	0.0530	0.5691	0.5975	0.049*
C9	0.4042 (6)	−0.5247 (16)	0.5729 (5)	0.098 (3)	0.910 (8)
H9A	0.4538	−0.3979	0.5624	0.147*	0.910 (8)
H9B	0.3516	−0.5661	0.5116	0.147*	0.910 (8)
H9C	0.4403	−0.6878	0.6010	0.147*	0.910 (8)
C9'	0.367 (4)	−0.529 (11)	0.878 (4)	0.041 (18)	0.090 (8)
H9'A	0.4200	−0.6566	0.8750	0.061*	0.090 (8)
H9'B	0.3956	−0.4078	0.9317	0.061*	0.090 (8)
H9'C	0.3080	−0.6241	0.8861	0.061*	0.090 (8)
O2	0.0524 (3)	0.1884 (9)	0.2803 (2)	0.0583 (12)
H21	0.0046	0.3006	0.2619	0.087*
H22	0.0756	0.1747	0.3415	0.087*

	U11	U22	U33	U12	U13	U23
O1	0.071 (3)	0.067 (3)	0.038 (2)	0.022 (2)	0.016 (2)	−0.002 (2)
N1	0.054 (3)	0.047 (3)	0.040 (3)	0.010 (3)	0.015 (2)	−0.002 (2)
C1	0.038 (3)	0.038 (4)	0.057 (4)	−0.006 (3)	0.006 (3)	−0.005 (3)
C2	0.052 (4)	0.055 (4)	0.067 (4)	0.000 (4)	0.018 (3)	0.002 (4)
C3	0.043 (4)	0.053 (5)	0.101 (6)	0.005 (4)	0.018 (4)	0.003 (4)
C4	0.057 (5)	0.056 (5)	0.098 (6)	0.010 (4)	0.001 (4)	0.020 (5)
C5	0.080 (6)	0.070 (6)	0.080 (5)	0.009 (5)	0.006 (4)	0.023 (5)
C6	0.067 (4)	0.058 (5)	0.054 (4)	0.007 (4)	0.007 (3)	0.009 (4)
C7	0.046 (4)	0.035 (4)	0.037 (3)	−0.004 (3)	0.007 (3)	0.000 (3)
C8	0.051 (3)	0.035 (4)	0.036 (3)	0.006 (3)	0.014 (3)	−0.001 (3)
C9	0.086 (6)	0.099 (7)	0.121 (7)	0.037 (5)	0.051 (5)	0.005 (6)
C9'	0.041 (18)	0.040 (19)	0.040 (18)	0.000 (5)	0.013 (7)	0.001 (5)
O2	0.079 (3)	0.062 (3)	0.037 (2)	0.012 (2)	0.023 (2)	0.008 (2)

O1—C7	1.219 (5)	C6—H6	0.9300
N1—C7	1.340 (6)	C7—C8	1.509 (6)
N1—C1	1.409 (6)	C8—C8i	1.492 (8)
N1—H1N	0.8600	C8—H8A	0.9700
C1—C2	1.378 (7)	C8—H8B	0.9700
C1—C6	1.385 (7)	C9—H9A	0.9600
C2—C3	1.398 (8)	C9—H9B	0.9600
C2—H2	0.9300	C9—H9C	0.9600
C3—C4	1.368 (8)	C9'—H9'A	0.9600
C3—C9	1.466 (8)	C9'—H9'B	0.9600
C4—C5	1.358 (8)	C9'—H9'C	0.9600
C4—H4	0.9300	O2—H21	0.8235
C5—C6	1.375 (8)	O2—H22	0.8398
C5—H5	0.9300
C7—N1—C1	130.1 (5)	C1—C6—H6	120.3
C7—N1—H1N	115.0	O1—C7—N1	122.8 (5)
C1—N1—H1N	115.0	O1—C7—C8	123.2 (5)
C2—C1—C6	119.1 (6)	N1—C7—C8	114.0 (5)
C2—C1—N1	123.6 (5)	C8i—C8—C7	113.5 (5)
C6—C1—N1	117.2 (5)	C8i—C8—H8A	108.9
C1—C2—C3	120.6 (6)	C7—C8—H8A	108.9
C1—C2—H2	119.7	C8i—C8—H8B	108.9
C3—C2—H2	119.7	C7—C8—H8B	108.9
C4—C3—C2	119.2 (6)	H8A—C8—H8B	107.7
C4—C3—C9	121.1 (7)	C3—C9—H9A	109.5
C2—C3—C9	119.7 (7)	C3—C9—H9B	109.5
C5—C4—C3	120.1 (7)	H9A—C9—H9B	109.5
C5—C4—H4	119.9	C3—C9—H9C	109.5
C3—C4—H4	119.9	H9A—C9—H9C	109.5
C4—C5—C6	121.5 (7)	H9B—C9—H9C	109.5
C4—C5—H5	119.2	H9'A—C9'—H9'B	109.5
C6—C5—H5	119.2	H9'A—C9'—H9'C	109.5
C5—C6—C1	119.4 (6)	H9'B—C9'—H9'C	109.5
C5—C6—H6	120.3	H21—O2—H22	112.4
C7—N1—C1—C2	5.4 (9)	C3—C4—C5—C6	−1.5 (11)
C7—N1—C1—C6	−173.6 (5)	C4—C5—C6—C1	1.3 (10)
C6—C1—C2—C3	−0.3 (8)	C2—C1—C6—C5	−0.4 (9)
N1—C1—C2—C3	−179.4 (5)	N1—C1—C6—C5	178.7 (5)
C1—C2—C3—C4	0.1 (9)	C1—N1—C7—O1	−1.5 (9)
C1—C2—C3—C9	179.4 (6)	C1—N1—C7—C8	177.3 (5)
C2—C3—C4—C5	0.8 (10)	O1—C7—C8—C8i	−5.3 (9)
C9—C3—C4—C5	−178.5 (7)	N1—C7—C8—C8i	175.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ii	0.86	2.10	2.946 (6)	169.
O2—H21···O2iii	0.82	2.08	2.836 (4)	153.
O2—H22···O1	0.84	1.87	2.713 (5)	178.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.10	2.946 (6)	169
O2—H21⋯O2ii	0.82	2.08	2.836 (4)	153
O2—H22⋯O1	0.84	1.87	2.713 (5)	178

Symmetry codes: (i) ; (ii) .