1,1'-[(5-Hy-droxy-methyl-1,3-phenyl-ene)bis-(methyl-ene)]dipyridin-4(1H)-one monohydrate.

The asymmetric unit of the title compound, C(19)H(18)N(2)O(3), comprises a whole organic dipyridinone mol-ecule plus a water mol-ecule of crystallization. The planes of the pyridinone rings are approximately perpendicular with the plane of the central aromatic ring [dihedral angles = 80.68 (8) and 83.65 (8)°]. The C-O bond of the hy-droxy group subtends an angle of 31.71 (10)° with the plane through the central aromatic ring. The crystal packing is mediated by the presence of several O-H⋯O hydrogen-bonding inter-actions and while the water mol-ecules form a C(2) (1)(4) chain parallel to the c axis of the unit cell, the pendant hy-droxy groups are engaged in O-H⋯O=C hydrogen bonds described by a C(1) (1)(12) graph-set motif which runs parallel to the a axis.

Related literature

For previous reports on the design and synthesis of mol­ecules based on a mesitylene core, see: Reger et al. (2010 ▶); Podyachev et al. (2006 ▶); Spiccia et al.(1997 ▶); Newkome et al. (1986 ▶); Berl et al., (2002 ▶). For the crystal structure and vibrational features of the precursor, 1,3,5-tris­(bromo­meth­yl)benzene, see: Fernandes et al. (2011 ▶). For a systematization of the graph-set notation for hydrogen-bonded aggregates, see: Grell et al. (1999 ▶).

Experimental

Crystal data

C19H18N2O3·H2O

M = 340.37

Monoclinic,

a = 12.2215 (8) Å

b = 14.1521 (10) Å

c = 10.3326 (7) Å

β = 114.720 (3)°

V = 1623.36 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 180 K

0.16 × 0.10 × 0.10 mm

Data collection

Bruker X8 KappaCCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.984, T max = 0.990

79090 measured reflections

2188 independent reflections

2103 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.077

S = 1.07

2188 reflections

233 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024809/tk2759sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024809/tk2759Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024809/tk2759Isup3.cml

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

C19H18N2O3·H2O	F(000) = 720
Mr = 340.37	Dx = 1.393 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 9702 reflections
a = 12.2215 (8) Å	θ = 2.6–29.1°
b = 14.1521 (10) Å	µ = 0.10 mm−1
c = 10.3326 (7) Å	T = 180 K
β = 114.720 (3)°	Block, colourless
V = 1623.36 (19) Å3	0.16 × 0.10 × 0.10 mm
Z = 4

Bruker X8 KappaCCD APEXII diffractometer	2188 independent reflections
Radiation source: fine-focus sealed tube	2103 reflections with I > 2σ(I)
graphite	Rint = 0.044
ω and φ scans	θmax = 29.1°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −16→16
Tmin = 0.984, Tmax = 0.990	k = −19→19
79090 measured reflections	l = −14→14

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077	w = 1/[σ2(Fo2) + (0.0434P)2 + 0.5107P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2188 reflections	Δρmax = 0.26 e Å−3
233 parameters	Δρmin = −0.20 e Å−3
5 restraints	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

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
N1	0.92401 (12)	0.28077 (10)	0.65493 (14)	0.0187 (3)
N2	0.79193 (12)	0.00864 (10)	0.34079 (15)	0.0196 (3)
O1	0.38592 (12)	0.23425 (10)	0.59461 (18)	0.0387 (4)
H1	0.3109	0.2418	0.5601	0.058*
O2	1.15708 (12)	0.29372 (10)	0.46529 (15)	0.0317 (3)
O3	1.14843 (12)	−0.01091 (12)	0.42158 (16)	0.0384 (4)
C1	0.41238 (14)	0.14197 (11)	0.56300 (19)	0.0216 (3)
H1A	0.3467	0.1195	0.4735	0.026*
H1B	0.4184	0.0982	0.6405	0.026*
C2	0.53025 (14)	0.14250 (10)	0.54728 (17)	0.0175 (3)
C3	0.62390 (14)	0.20213 (11)	0.63200 (17)	0.0181 (3)
H3	0.6132	0.2432	0.6985	0.022*
C4	0.73306 (14)	0.20150 (11)	0.61923 (16)	0.0174 (3)
C5	0.74897 (14)	0.14000 (11)	0.52290 (17)	0.0182 (3)
H5	0.8241	0.1382	0.5160	0.022*
C6	0.65561 (14)	0.08125 (11)	0.43687 (17)	0.0179 (3)
C7	0.54605 (14)	0.08265 (11)	0.44961 (17)	0.0185 (3)
H7	0.4821	0.0425	0.3913	0.022*
C8	0.83252 (14)	0.26795 (12)	0.71127 (18)	0.0210 (3)
H8A	0.7972	0.3301	0.7161	0.025*
H8B	0.8714	0.2423	0.8092	0.025*
C9	0.89558 (15)	0.33240 (12)	0.53364 (18)	0.0217 (3)
H9	0.8219	0.3665	0.4953	0.026*
C10	0.97013 (15)	0.33616 (12)	0.46626 (19)	0.0231 (3)
H10	0.9469	0.3717	0.3809	0.028*
C11	1.08376 (14)	0.28714 (12)	0.52208 (18)	0.0222 (3)
C12	1.10808 (15)	0.23253 (12)	0.64795 (19)	0.0247 (4)
H12	1.1806	0.1971	0.6892	0.030*
C13	1.02879 (15)	0.23077 (12)	0.70921 (17)	0.0221 (3)
H13	1.0471	0.1936	0.7922	0.027*
C14	0.66668 (14)	0.01871 (12)	0.32359 (19)	0.0229 (3)
H14A	0.6339	−0.0446	0.3278	0.027*
H14B	0.6175	0.0458	0.2285	0.027*
C15	0.84155 (16)	0.07180 (13)	0.28150 (19)	0.0245 (3)
H15	0.7922	0.1199	0.2209	0.029*
C16	0.96049 (16)	0.06788 (13)	0.30689 (19)	0.0265 (4)
H16	0.9922	0.1132	0.2639	0.032*
C17	1.03820 (16)	−0.00342 (13)	0.39709 (19)	0.0253 (4)
C18	0.98150 (16)	−0.06684 (13)	0.45843 (19)	0.0265 (4)
H18	1.0280	−0.1153	0.5208	0.032*
C19	0.86260 (16)	−0.05917 (11)	0.42929 (18)	0.0229 (3)
H19	0.8281	−0.1024	0.4720	0.027*
O1W	0.26763 (13)	0.99519 (12)	0.23725 (16)	0.0365 (3)
H1X	0.216 (2)	0.998 (2)	0.283 (2)	0.055*
H1Y	0.224 (2)	0.999 (2)	0.1375 (11)	0.055*

	U11	U22	U33	U12	U13	U23
N1	0.0158 (6)	0.0206 (6)	0.0200 (6)	−0.0034 (5)	0.0077 (5)	−0.0024 (5)
N2	0.0178 (6)	0.0221 (6)	0.0206 (6)	0.0011 (5)	0.0096 (5)	−0.0030 (5)
O1	0.0209 (6)	0.0327 (7)	0.0641 (10)	0.0020 (5)	0.0195 (7)	−0.0139 (7)
O2	0.0235 (6)	0.0414 (7)	0.0351 (7)	0.0019 (6)	0.0172 (6)	0.0058 (6)
O3	0.0206 (6)	0.0613 (10)	0.0345 (8)	0.0042 (6)	0.0126 (6)	0.0033 (7)
C1	0.0175 (7)	0.0236 (7)	0.0267 (8)	0.0006 (6)	0.0121 (6)	0.0023 (6)
C2	0.0153 (6)	0.0193 (7)	0.0188 (7)	0.0018 (6)	0.0080 (6)	0.0048 (6)
C3	0.0183 (7)	0.0190 (7)	0.0190 (7)	0.0012 (6)	0.0099 (6)	−0.0004 (6)
C4	0.0159 (7)	0.0187 (7)	0.0173 (7)	−0.0005 (5)	0.0064 (6)	0.0004 (5)
C5	0.0142 (6)	0.0215 (7)	0.0202 (7)	−0.0005 (6)	0.0085 (6)	−0.0028 (6)
C6	0.0184 (7)	0.0180 (6)	0.0180 (7)	0.0012 (5)	0.0081 (6)	−0.0003 (5)
C7	0.0157 (7)	0.0182 (7)	0.0206 (7)	−0.0012 (5)	0.0067 (6)	0.0008 (6)
C8	0.0178 (7)	0.0248 (8)	0.0227 (7)	−0.0043 (6)	0.0107 (6)	−0.0064 (6)
C9	0.0178 (7)	0.0206 (7)	0.0241 (8)	0.0000 (6)	0.0063 (6)	0.0008 (6)
C10	0.0203 (7)	0.0246 (8)	0.0233 (7)	−0.0006 (6)	0.0081 (6)	0.0045 (6)
C11	0.0196 (8)	0.0227 (8)	0.0250 (8)	−0.0034 (6)	0.0099 (7)	−0.0025 (6)
C12	0.0192 (8)	0.0242 (8)	0.0294 (9)	0.0021 (6)	0.0090 (7)	0.0041 (7)
C13	0.0193 (7)	0.0214 (7)	0.0231 (8)	−0.0008 (6)	0.0063 (6)	0.0024 (6)
C14	0.0159 (7)	0.0287 (8)	0.0248 (8)	−0.0021 (6)	0.0092 (6)	−0.0092 (7)
C15	0.0263 (8)	0.0250 (8)	0.0237 (8)	0.0035 (6)	0.0120 (7)	0.0032 (6)
C16	0.0258 (8)	0.0313 (9)	0.0260 (9)	−0.0011 (7)	0.0144 (7)	0.0028 (7)
C17	0.0224 (8)	0.0328 (9)	0.0217 (8)	0.0012 (7)	0.0103 (7)	−0.0026 (7)
C18	0.0261 (9)	0.0273 (8)	0.0269 (8)	0.0071 (7)	0.0118 (7)	0.0055 (7)
C19	0.0271 (8)	0.0200 (7)	0.0246 (8)	−0.0001 (6)	0.0139 (7)	0.0004 (6)
O1W	0.0245 (6)	0.0518 (9)	0.0308 (7)	−0.0028 (6)	0.0091 (6)	−0.0021 (6)

N1—C13	1.362 (2)	C7—H7	0.9500
N1—C9	1.364 (2)	C8—H8A	0.9900
N1—C8	1.472 (2)	C8—H8B	0.9900
N2—C19	1.357 (2)	C9—C10	1.359 (2)
N2—C15	1.361 (2)	C9—H9	0.9500
N2—C14	1.472 (2)	C10—C11	1.440 (2)
O1—C1	1.416 (2)	C10—H10	0.9500
O1—H1	0.8400	C11—C12	1.433 (2)
O2—C11	1.263 (2)	C12—C13	1.361 (2)
O3—C17	1.267 (2)	C12—H12	0.9500
C1—C2	1.516 (2)	C13—H13	0.9500
C1—H1A	0.9900	C14—H14A	0.9900
C1—H1B	0.9900	C14—H14B	0.9900
C2—C7	1.391 (2)	C15—C16	1.366 (2)
C2—C3	1.397 (2)	C15—H15	0.9500
C3—C4	1.394 (2)	C16—C17	1.431 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.396 (2)	C17—C18	1.433 (3)
C4—C8	1.516 (2)	C18—C19	1.360 (2)
C5—C6	1.391 (2)	C18—H18	0.9500
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.399 (2)	O1W—H1X	0.936 (10)
C6—C14	1.518 (2)	O1W—H1Y	0.943 (10)
C13—N1—C9	119.41 (14)	C10—C9—N1	121.57 (15)
C13—N1—C8	120.81 (14)	C10—C9—H9	119.2
C9—N1—C8	119.05 (14)	N1—C9—H9	119.2
C19—N2—C15	119.32 (14)	C9—C10—C11	121.12 (15)
C19—N2—C14	119.10 (14)	C9—C10—H10	119.4
C15—N2—C14	121.23 (15)	C11—C10—H10	119.4
C1—O1—H1	109.5	O2—C11—C12	122.89 (16)
O1—C1—C2	109.83 (13)	O2—C11—C10	122.09 (15)
O1—C1—H1A	109.7	C12—C11—C10	115.00 (14)
C2—C1—H1A	109.7	C13—C12—C11	120.93 (15)
O1—C1—H1B	109.7	C13—C12—H12	119.5
C2—C1—H1B	109.7	C11—C12—H12	119.5
H1A—C1—H1B	108.2	C12—C13—N1	121.92 (15)
C7—C2—C3	119.77 (14)	C12—C13—H13	119.0
C7—C2—C1	120.07 (14)	N1—C13—H13	119.0
C3—C2—C1	120.15 (14)	N2—C14—C6	112.76 (13)
C4—C3—C2	120.17 (14)	N2—C14—H14A	109.0
C4—C3—H3	119.9	C6—C14—H14A	109.0
C2—C3—H3	119.9	N2—C14—H14B	109.0
C3—C4—C5	119.71 (14)	C6—C14—H14B	109.0
C3—C4—C8	118.98 (13)	H14A—C14—H14B	107.8
C5—C4—C8	121.31 (13)	N2—C15—C16	121.70 (16)
C6—C5—C4	120.45 (14)	N2—C15—H15	119.1
C6—C5—H5	119.8	C16—C15—H15	119.1
C4—C5—H5	119.8	C15—C16—C17	121.11 (16)
C5—C6—C7	119.53 (14)	C15—C16—H16	119.4
C5—C6—C14	121.83 (14)	C17—C16—H16	119.4
C7—C6—C14	118.56 (14)	O3—C17—C16	123.34 (17)
C2—C7—C6	120.35 (14)	O3—C17—C18	121.98 (17)
C2—C7—H7	119.8	C16—C17—C18	114.68 (15)
C6—C7—H7	119.8	C19—C18—C17	121.44 (16)
N1—C8—C4	111.76 (13)	C19—C18—H18	119.3
N1—C8—H8A	109.3	C17—C18—H18	119.3
C4—C8—H8A	109.3	N2—C19—C18	121.72 (15)
N1—C8—H8B	109.3	N2—C19—H19	119.1
C4—C8—H8B	109.3	C18—C19—H19	119.1
H8A—C8—H8B	107.9	H1X—O1W—H1Y	111.4 (15)
O1—C1—C2—C7	−145.77 (15)	C9—C10—C11—O2	−176.23 (17)
O1—C1—C2—C3	35.1 (2)	C9—C10—C11—C12	2.4 (2)
C7—C2—C3—C4	−0.2 (2)	O2—C11—C12—C13	177.05 (17)
C1—C2—C3—C4	178.93 (14)	C10—C11—C12—C13	−1.6 (2)
C2—C3—C4—C5	−0.9 (2)	C11—C12—C13—N1	−0.4 (3)
C2—C3—C4—C8	179.21 (14)	C9—N1—C13—C12	1.7 (2)
C3—C4—C5—C6	1.8 (2)	C8—N1—C13—C12	171.78 (15)
C8—C4—C5—C6	−178.39 (15)	C19—N2—C14—C6	85.84 (19)
C4—C5—C6—C7	−1.4 (2)	C15—N2—C14—C6	−87.4 (2)
C4—C5—C6—C14	175.51 (15)	C5—C6—C14—N2	15.0 (2)
C3—C2—C7—C6	0.6 (2)	C7—C6—C14—N2	−168.12 (14)
C1—C2—C7—C6	−178.55 (15)	C19—N2—C15—C16	1.1 (2)
C5—C6—C7—C2	0.2 (2)	C14—N2—C15—C16	174.26 (16)
C14—C6—C7—C2	−176.82 (15)	N2—C15—C16—C17	0.2 (3)
C13—N1—C8—C4	−98.31 (17)	C15—C16—C17—O3	178.65 (18)
C9—N1—C8—C4	71.82 (18)	C15—C16—C17—C18	−1.2 (3)
C3—C4—C8—N1	−161.86 (14)	O3—C17—C18—C19	−178.78 (17)
C5—C4—C8—N1	18.3 (2)	C16—C17—C18—C19	1.1 (3)
C13—N1—C9—C10	−0.8 (2)	C15—N2—C19—C18	−1.2 (2)
C8—N1—C9—C10	−171.09 (15)	C14—N2—C19—C18	−174.54 (16)
N1—C9—C10—C11	−1.3 (3)	C17—C18—C19—N2	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1X···O3i	0.94 (1)	1.93 (1)	2.842 (2)	164 (2)
O1W—H1Y···O3ii	0.94 (1)	2.03 (1)	2.973 (2)	174 (2)
O1—H1···O2iii	0.84	1.87	2.6814 (19)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1X⋯O3i	0.94 (1)	1.93 (1)	2.842 (2)	164 (2)
O1W—H1Y⋯O3ii	0.94 (1)	2.03 (1)	2.973 (2)	174 (2)
O1—H1⋯O2iii	0.84	1.87	2.6814 (19)	162

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