N,N'-(2-Hy-droxy-propane-1,3-di-yl)bis-(2-hy-droxy-benzamide) monohydrate.

In the title hydrate, C17H18N2O5·H2O, the complete organic mol-ecule is generated by a crystallographic mirror plane with one C and one O atom lying on the mirror plane. The O atom of the water mol-ecule has m site symmetry. Two symmetry-related intra-molecular O-H⋯O hydrogen bonds complete S(6) rings in the organic mol-ecule. In the crystal, the components are linked into (010) sheets by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the synthesis of similar compounds and their complexes see: Kumar & Debashis (2006 ▶); Azam et al. (2012 ▶); Sarkar (1999 ▶); Louhibi et al. (2007 ▶); Kui et al. (2009 ▶).

Experimental

Crystal data

C17H18N2O5·H2O

M = 348.35

Orthorhombic,

a = 12.8969 (10) Å

b = 28.001 (2) Å

c = 4.5330 (4) Å

V = 1637.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 150 K

0.38 × 0.12 × 0.04 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.877, T max = 0.996

7880 measured reflections

1904 independent reflections

1195 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.123

S = 1.04

1904 reflections

124 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CRYSCAL (T. Roisnel, local program).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813026184/hb7142sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026184/hb7142Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813026184/hb7142Isup3.cml

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

C17H18N2O5·H2O	F(000) = 736
Mr = 348.35	Dx = 1.413 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 951 reflections
a = 12.8969 (10) Å	θ = 3.2–21.6°
b = 28.001 (2) Å	µ = 0.11 mm−1
c = 4.5330 (4) Å	T = 150 K
V = 1637.0 (2) Å3	Prism, yellow
Z = 4	0.38 × 0.12 × 0.04 mm

Bruker APEXII diffractometer	1195 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
CCD rotation images, thin slices scans	θmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2011)	h = −16→15
Tmin = 0.877, Tmax = 0.996	k = −33→36
7880 measured reflections	l = −3→5
1904 independent reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0542P)2] where P = (Fo2 + 2Fc2)/3
1904 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.39517 (14)	0.25000	0.2499 (4)	0.0247 (6)
O6	0.12018 (10)	0.17317 (5)	−0.0499 (3)	0.0305 (5)
O13	−0.01478 (10)	0.12722 (5)	0.2259 (4)	0.0365 (5)
N4	0.29166 (11)	0.16318 (5)	0.0274 (3)	0.0222 (5)
C2	0.3155 (2)	0.25000	0.0315 (6)	0.0220 (8)
C3	0.31907 (14)	0.20435 (6)	−0.1551 (4)	0.0231 (6)
C5	0.19276 (14)	0.15119 (6)	0.0789 (4)	0.0221 (6)
C7	0.16854 (13)	0.11226 (6)	0.2905 (4)	0.0211 (6)
C8	0.24447 (14)	0.08491 (6)	0.4318 (4)	0.0246 (6)
C9	0.21836 (16)	0.04885 (7)	0.6277 (5)	0.0299 (7)
C10	0.11462 (16)	0.03987 (7)	0.6864 (5)	0.0324 (7)
C11	0.03789 (16)	0.06622 (7)	0.5520 (5)	0.0324 (7)
C12	0.06373 (14)	0.10227 (7)	0.3538 (5)	0.0266 (6)
O1W	0.08072 (15)	0.25000	0.5613 (5)	0.0345 (7)
H1	0.460 (2)	0.25000	0.145 (7)	0.0370*
H2	0.24766	0.25000	0.13838	0.0264*
H3A	0.26982	0.20707	−0.32177	0.0278*
H3B	0.38959	0.20000	−0.23708	0.0278*
H4	0.34148	0.14581	0.10545	0.0266*
H8	0.31554	0.09118	0.39263	0.0295*
H9	0.27095	0.03049	0.72084	0.0359*
H10	0.09631	0.01526	0.82091	0.0389*
H11	−0.03286	0.05978	0.59456	0.0389*
H13	0.01003	0.14928	0.12199	0.0547*
H1W	0.0926 (17)	0.2238 (8)	0.677 (6)	0.0517*

	U11	U22	U33	U12	U13	U23
O1	0.0203 (10)	0.0348 (11)	0.0189 (11)	0.0000	0.0017 (9)	0.0000
O6	0.0194 (7)	0.0361 (8)	0.0359 (9)	0.0012 (6)	−0.0039 (7)	0.0057 (7)
O13	0.0166 (7)	0.0423 (9)	0.0506 (11)	−0.0004 (6)	0.0023 (7)	0.0076 (8)
N4	0.0185 (8)	0.0223 (8)	0.0258 (10)	0.0002 (6)	0.0017 (7)	0.0005 (7)
C2	0.0183 (13)	0.0282 (14)	0.0196 (15)	0.0000	0.0013 (12)	0.0000
C3	0.0206 (10)	0.0277 (10)	0.0211 (10)	−0.0012 (8)	0.0026 (9)	0.0016 (9)
C5	0.0208 (9)	0.0252 (10)	0.0202 (10)	−0.0002 (8)	0.0012 (9)	−0.0063 (9)
C7	0.0196 (9)	0.0225 (9)	0.0211 (11)	−0.0024 (7)	0.0020 (9)	−0.0043 (8)
C8	0.0205 (10)	0.0272 (10)	0.0262 (11)	−0.0032 (7)	0.0014 (9)	−0.0036 (9)
C9	0.0323 (11)	0.0277 (11)	0.0298 (12)	−0.0008 (9)	−0.0029 (10)	−0.0020 (9)
C10	0.0375 (12)	0.0319 (12)	0.0279 (13)	−0.0092 (9)	0.0060 (10)	0.0005 (10)
C11	0.0263 (11)	0.0357 (12)	0.0353 (13)	−0.0105 (9)	0.0079 (10)	−0.0018 (10)
C12	0.0218 (10)	0.0290 (11)	0.0291 (12)	−0.0010 (8)	0.0009 (10)	−0.0072 (9)
O1W	0.0306 (11)	0.0388 (12)	0.0340 (14)	0.0000	−0.0103 (10)	0.0000

O1—C2	1.427 (3)	C7—C8	1.399 (2)
O6—C5	1.263 (2)	C7—C12	1.410 (2)
O13—C12	1.360 (2)	C8—C9	1.386 (3)
O1—H1	0.96 (3)	C9—C10	1.387 (3)
O13—H13	0.8400	C10—C11	1.377 (3)
O1W—H1Wi	0.92 (2)	C11—C12	1.392 (3)
O1W—H1W	0.92 (2)	C2—H2	1.0000
N4—C5	1.340 (2)	C3—H3B	0.9900
N4—C3	1.462 (2)	C3—H3A	0.9900
N4—H4	0.8800	C8—H8	0.9500
C2—C3	1.534 (2)	C9—H9	0.9500
C2—C3i	1.534 (2)	C10—H10	0.9500
C5—C7	1.485 (2)	C11—H11	0.9500
C2—O1—H1	106.4 (18)	C7—C12—C11	120.32 (18)
C12—O13—H13	109.00	O13—C12—C7	121.68 (18)
H1W—O1W—H1Wi	107 (2)	O13—C12—C11	118.00 (17)
C3—N4—C5	121.76 (14)	O1—C2—H2	107.00
C3—N4—H4	119.00	C3i—C2—H2	107.00
C5—N4—H4	119.00	C3—C2—H2	107.00
O1—C2—C3i	111.17 (13)	N4—C3—H3B	110.00
O1—C2—C3	111.17 (13)	C2—C3—H3A	110.00
C3—C2—C3i	112.93 (19)	N4—C3—H3A	110.00
N4—C3—C2	109.75 (15)	H3A—C3—H3B	108.00
O6—C5—N4	120.19 (16)	C2—C3—H3B	110.00
N4—C5—C7	119.79 (15)	C7—C8—H8	119.00
O6—C5—C7	120.01 (16)	C9—C8—H8	119.00
C5—C7—C12	118.60 (16)	C10—C9—H9	120.00
C8—C7—C12	118.00 (16)	C8—C9—H9	120.00
C5—C7—C8	123.40 (15)	C9—C10—H10	120.00
C7—C8—C9	121.48 (17)	C11—C10—H10	120.00
C8—C9—C10	119.29 (19)	C10—C11—H11	120.00
C9—C10—C11	120.75 (19)	C12—C11—H11	120.00
C10—C11—C12	120.15 (19)
C3—N4—C5—O6	5.8 (3)	C12—C7—C8—C9	0.3 (3)
C3—N4—C5—C7	−173.61 (15)	C5—C7—C12—O13	0.2 (3)
C5—N4—C3—C2	83.3 (2)	C5—C7—C12—C11	−179.68 (18)
O1—C2—C3—N4	67.2 (2)	C8—C7—C12—O13	179.97 (19)
C3i—C2—C3—N4	−167.07 (16)	C8—C7—C12—C11	0.1 (3)
O6—C5—C7—C8	177.11 (17)	C7—C8—C9—C10	−0.4 (3)
O6—C5—C7—C12	−3.1 (3)	C8—C9—C10—C11	0.2 (3)
N4—C5—C7—C8	−3.5 (3)	C9—C10—C11—C12	0.2 (3)
N4—C5—C7—C12	176.29 (17)	C10—C11—C12—O13	179.8 (2)
C5—C7—C8—C9	−179.93 (17)	C10—C11—C12—C7	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1Wii	0.96 (3)	1.82 (3)	2.778 (3)	179 (3)
O1W—H1W···O6iii	0.92 (2)	1.92 (2)	2.827 (2)	174 (2)
O13—H13···O6	0.84	1.75	2.500 (2)	147
N4—H4···O13iv	0.88	2.07	2.915 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1W i	0.96 (3)	1.82 (3)	2.778 (3)	179 (3)
O1W—H1W⋯O6ii	0.92 (2)	1.92 (2)	2.827 (2)	174 (2)
O13—H13⋯O6	0.84	1.75	2.500 (2)	147
N4—H4⋯O13iii	0.88	2.07	2.915 (2)	160

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