N-(4-Methyl-phen-yl)-N'-phenyl-butane-diamide monohydrate.

In the title hydrate, C(17)H(18)N(2)O(2)·H(2)O, the dihedral angles formed by the aromatic rings of the benzene and methyl-benzene groups with the mean planes of the attached NH-C(O)-CH(2) fragments are 12.6 (4) and 23.3 (3)°, respectively, while that between the two aromatic rings is 73.7 (2)°. In the crystal, the water mol-ecule accepts two and makes two hydrogen bonds. The mol-ecules are packed into layers parallel to (101) by O-H⋯O and N-H⋯O hydrogen-bonding inter-actions.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶); Saraswathi et al. (2011 ▶) and on the structures of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶). For restrained geometry, see: Nardelli (1999 ▶).

Experimental

Crystal data

C17H18N2O2·H2O

M = 300.35

Monoclinic,

a = 15.242 (4) Å

b = 4.905 (1) Å

c = 21.540 (5) Å

β = 102.90 (2)°

V = 1569.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.44 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.962, T max = 0.993

5068 measured reflections

2805 independent reflections

1356 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.117

wR(F 2) = 0.239

S = 1.16

2805 reflections

211 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.31 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 datablocks I, global. DOI: 10.1107/S1600536811018915/tk2744sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018915/tk2744Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018915/tk2744Isup3.cml

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

C17H18N2O2·H2O	F(000) = 640
Mr = 300.35	Dx = 1.271 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 897 reflections
a = 15.242 (4) Å	θ = 2.6–27.8°
b = 4.905 (1) Å	µ = 0.09 mm−1
c = 21.540 (5) Å	T = 293 K
β = 102.90 (2)°	Needle, colourless
V = 1569.7 (6) Å3	0.44 × 0.12 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2805 independent reflections
Radiation source: fine-focus sealed tube	1356 reflections with I > 2σ(I)
graphite	Rint = 0.058
Rotation method data acquisition using ω scans	θmax = 25.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −18→15
Tmin = 0.962, Tmax = 0.993	k = −5→4
5068 measured reflections	l = −25→21

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)] = 0.117	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.239	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0521P)2 + 3.417P] where P = (Fo2 + 2Fc2)/3
2805 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.35 e Å−3
5 restraints	Δρmin = −0.31 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	1.1172 (4)	0.2471 (13)	0.3698 (3)	0.0477 (16)
C2	1.0806 (5)	0.4142 (15)	0.3191 (3)	0.063 (2)
H2	1.0187	0.4183	0.3031	0.076*
C3	1.1363 (6)	0.5749 (17)	0.2923 (4)	0.080 (2)
H3	1.1113	0.6843	0.2576	0.096*
C4	1.2289 (6)	0.5780 (17)	0.3157 (4)	0.090 (3)
H4	1.2656	0.6879	0.2971	0.108*
C5	1.2648 (5)	0.4153 (18)	0.3667 (4)	0.089 (3)
H5	1.3267	0.4150	0.3831	0.107*
C6	1.2101 (4)	0.2525 (16)	0.3940 (3)	0.071 (2)
H6	1.2354	0.1448	0.4289	0.085*
C7	0.9812 (4)	−0.0135 (12)	0.3804 (3)	0.0426 (16)
C8	0.9514 (3)	−0.2274 (13)	0.4215 (3)	0.0440 (16)
H8A	0.9736	−0.1789	0.4659	0.053*
H8B	0.9781	−0.4008	0.4144	0.053*
C9	0.8499 (4)	−0.2600 (12)	0.4085 (3)	0.0487 (17)
H9A	0.8356	−0.4171	0.4317	0.058*
H9B	0.8272	−0.2944	0.3634	0.058*
C10	0.8029 (4)	−0.0102 (12)	0.4276 (3)	0.0418 (16)
C11	0.6627 (4)	0.2679 (12)	0.3937 (3)	0.0399 (15)
C12	0.6588 (4)	0.3788 (13)	0.4515 (3)	0.0477 (17)
H7	0.6988	0.3221	0.4884	0.057*
C13	0.5948 (4)	0.5757 (14)	0.4546 (3)	0.0555 (18)
H13	0.5927	0.6499	0.4940	0.067*
C14	0.5343 (4)	0.6647 (12)	0.4013 (4)	0.0497 (17)
C15	0.5394 (4)	0.5532 (14)	0.3437 (3)	0.0569 (19)
H15	0.4995	0.6109	0.3068	0.068*
C16	0.6028 (4)	0.3567 (13)	0.3398 (3)	0.0513 (17)
H16	0.6051	0.2835	0.3004	0.062*
C17	0.4654 (5)	0.8807 (15)	0.4067 (4)	0.086 (3)
H17A	0.4060	0.8100	0.3904	0.103*
H17B	0.4746	1.0382	0.3824	0.103*
H17C	0.4719	0.9309	0.4505	0.103*
N1	1.0664 (3)	0.0735 (11)	0.4004 (2)	0.0475 (14)
H1N	1.095 (3)	−0.005 (11)	0.4340 (17)	0.057*
N2	0.7246 (3)	0.0584 (10)	0.3870 (2)	0.0421 (13)
H2N	0.716 (4)	−0.031 (10)	0.3519 (16)	0.051*
O1	0.9311 (3)	0.0725 (11)	0.3319 (2)	0.0762 (16)
O2	0.8342 (3)	0.1165 (8)	0.47672 (18)	0.0509 (12)
O3	0.7946 (3)	0.3120 (9)	0.2425 (2)	0.0596 (13)
H31	0.839 (3)	0.268 (11)	0.273 (2)	0.071*
H32	0.773 (4)	0.460 (8)	0.253 (3)	0.071*

	U11	U22	U33	U12	U13	U23
C1	0.054 (4)	0.044 (4)	0.040 (4)	−0.001 (4)	0.001 (3)	−0.004 (3)
C2	0.069 (5)	0.070 (5)	0.049 (4)	0.004 (4)	0.011 (4)	0.007 (4)
C3	0.102 (7)	0.073 (6)	0.063 (5)	0.011 (6)	0.011 (5)	0.020 (5)
C4	0.100 (7)	0.078 (6)	0.084 (6)	−0.026 (6)	0.003 (5)	0.008 (5)
C5	0.071 (5)	0.099 (7)	0.088 (6)	−0.024 (5)	−0.004 (5)	0.025 (6)
C6	0.057 (5)	0.076 (6)	0.068 (5)	−0.015 (4)	−0.009 (4)	0.015 (4)
C7	0.039 (3)	0.043 (4)	0.043 (4)	0.008 (3)	0.002 (3)	−0.005 (3)
C8	0.036 (3)	0.039 (4)	0.053 (4)	0.003 (3)	0.003 (3)	−0.008 (3)
C9	0.042 (4)	0.032 (4)	0.065 (4)	−0.002 (3)	−0.004 (3)	−0.011 (3)
C10	0.036 (3)	0.040 (4)	0.044 (4)	−0.009 (3)	−0.003 (3)	0.005 (3)
C11	0.037 (3)	0.034 (4)	0.045 (4)	−0.004 (3)	0.001 (3)	−0.003 (3)
C12	0.037 (3)	0.052 (4)	0.049 (4)	0.002 (3)	−0.001 (3)	−0.001 (4)
C13	0.047 (4)	0.060 (5)	0.058 (4)	−0.001 (4)	0.009 (3)	−0.007 (4)
C14	0.036 (4)	0.031 (4)	0.083 (5)	−0.002 (3)	0.015 (4)	0.003 (4)
C15	0.041 (4)	0.054 (5)	0.067 (5)	0.009 (4)	−0.004 (3)	0.013 (4)
C16	0.046 (4)	0.054 (4)	0.047 (4)	0.003 (4)	−0.004 (3)	0.005 (3)
C17	0.072 (5)	0.071 (6)	0.113 (7)	−0.001 (5)	0.016 (5)	0.004 (5)
N1	0.043 (3)	0.052 (4)	0.040 (3)	0.002 (3)	−0.005 (2)	0.012 (3)
N2	0.036 (3)	0.043 (3)	0.041 (3)	−0.002 (3)	−0.004 (2)	−0.009 (3)
O1	0.051 (3)	0.100 (4)	0.062 (3)	0.001 (3)	−0.020 (2)	0.032 (3)
O2	0.050 (3)	0.047 (3)	0.046 (2)	0.006 (2)	−0.010 (2)	−0.005 (2)
O3	0.060 (3)	0.053 (3)	0.056 (3)	0.009 (2)	−0.008 (2)	0.005 (2)

C1—C2	1.380 (8)	C10—O2	1.227 (6)
C1—C6	1.396 (8)	C10—N2	1.356 (6)
C1—N1	1.410 (8)	C11—C12	1.372 (8)
C2—C3	1.377 (10)	C11—C16	1.378 (7)
C2—H2	0.9300	C11—N2	1.424 (7)
C3—C4	1.388 (10)	C12—C13	1.385 (8)
C3—H3	0.9300	C12—H7	0.9300
C4—C5	1.370 (10)	C13—C14	1.373 (8)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.376 (9)	C14—C15	1.374 (9)
C5—H5	0.9300	C14—C17	1.515 (9)
C6—H6	0.9300	C15—C16	1.381 (8)
C7—O1	1.222 (6)	C15—H15	0.9300
C7—N1	1.343 (7)	C16—H16	0.9300
C7—C8	1.507 (8)	C17—H17A	0.9600
C8—C9	1.517 (7)	C17—H17B	0.9600
C8—H8A	0.9700	C17—H17C	0.9600
C8—H8B	0.9700	N1—H1N	0.85 (2)
C9—C10	1.522 (8)	N2—H2N	0.859 (19)
C9—H9A	0.9700	O3—H31	0.854 (19)
C9—H9B	0.9700	O3—H32	0.847 (19)
C2—C1—C6	118.8 (7)	O2—C10—C9	121.7 (5)
C2—C1—N1	124.2 (6)	N2—C10—C9	115.1 (5)
C6—C1—N1	117.0 (6)	C12—C11—C16	119.0 (6)
C3—C2—C1	119.6 (7)	C12—C11—N2	122.9 (5)
C3—C2—H2	120.2	C16—C11—N2	118.1 (5)
C1—C2—H2	120.2	C11—C12—C13	119.6 (6)
C2—C3—C4	121.7 (7)	C11—C12—H7	120.2
C2—C3—H3	119.1	C13—C12—H7	120.2
C4—C3—H3	119.1	C14—C13—C12	122.0 (6)
C5—C4—C3	118.5 (8)	C14—C13—H13	119.0
C5—C4—H4	120.8	C12—C13—H13	119.0
C3—C4—H4	120.8	C13—C14—C15	117.8 (6)
C4—C5—C6	120.6 (8)	C13—C14—C17	120.4 (7)
C4—C5—H5	119.7	C15—C14—C17	121.8 (6)
C6—C5—H5	119.7	C14—C15—C16	120.9 (6)
C5—C6—C1	120.8 (7)	C14—C15—H15	119.5
C5—C6—H6	119.6	C16—C15—H15	119.5
C1—C6—H6	119.6	C11—C16—C15	120.7 (6)
O1—C7—N1	122.6 (6)	C11—C16—H16	119.7
O1—C7—C8	122.0 (5)	C15—C16—H16	119.7
N1—C7—C8	115.4 (5)	C14—C17—H17A	109.5
C7—C8—C9	113.1 (5)	C14—C17—H17B	109.5
C7—C8—H8A	109.0	H17A—C17—H17B	109.5
C9—C8—H8A	109.0	C14—C17—H17C	109.5
C7—C8—H8B	109.0	H17A—C17—H17C	109.5
C9—C8—H8B	109.0	H17B—C17—H17C	109.5
H8A—C8—H8B	107.8	C7—N1—C1	129.4 (5)
C8—C9—C10	112.8 (5)	C7—N1—H1N	114 (4)
C8—C9—H9A	109.0	C1—N1—H1N	116 (4)
C10—C9—H9A	109.0	C10—N2—C11	128.4 (5)
C8—C9—H9B	109.0	C10—N2—H2N	113 (4)
C10—C9—H9B	109.0	C11—N2—H2N	119 (4)
H9A—C9—H9B	107.8	H31—O3—H32	107 (3)
O2—C10—N2	123.2 (6)
C6—C1—C2—C3	2.1 (10)	C12—C13—C14—C15	−0.5 (10)
N1—C1—C2—C3	−179.6 (6)	C12—C13—C14—C17	−179.9 (6)
C1—C2—C3—C4	−1.3 (12)	C13—C14—C15—C16	0.5 (10)
C2—C3—C4—C5	0.1 (13)	C17—C14—C15—C16	179.9 (6)
C3—C4—C5—C6	0.1 (13)	C12—C11—C16—C15	−0.3 (9)
C4—C5—C6—C1	0.7 (13)	N2—C11—C16—C15	177.9 (5)
C2—C1—C6—C5	−1.9 (11)	C14—C15—C16—C11	−0.1 (10)
N1—C1—C6—C5	179.7 (7)	O1—C7—N1—C1	−7.0 (10)
O1—C7—C8—C9	−16.9 (8)	C8—C7—N1—C1	172.5 (6)
N1—C7—C8—C9	163.6 (5)	C2—C1—N1—C7	16.7 (10)
C7—C8—C9—C10	−67.0 (7)	C6—C1—N1—C7	−165.0 (6)
C8—C9—C10—O2	−40.1 (8)	O2—C10—N2—C11	−4.1 (9)
C8—C9—C10—N2	140.3 (5)	C9—C10—N2—C11	175.4 (5)
C16—C11—C12—C13	0.3 (9)	C12—C11—N2—C10	−21.1 (9)
N2—C11—C12—C13	−177.9 (5)	C16—C11—N2—C10	160.7 (6)
C11—C12—C13—C14	0.1 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (2)	2.06 (2)	2.895 (6)	168 (6)
N2—H2N···O3ii	0.86 (2)	2.15 (2)	2.992 (6)	169 (5)
O3—H31···O1	0.85 (2)	1.93 (2)	2.762 (6)	165 (5)
O3—H32···O3iii	0.85 (2)	2.03 (2)	2.858 (5)	166 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (2)	2.06 (2)	2.895 (6)	168 (6)
N2—H2N⋯O3ii	0.86 (2)	2.15 (2)	2.992 (6)	169 (5)
O3—H31⋯O1	0.85 (2)	1.93 (2)	2.762 (6)	165 (5)
O3—H32⋯O3iii	0.85 (2)	2.03 (2)	2.858 (5)	166 (5)

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