Bis{2,6-bis­[(2-hy­droxy-5-methyl­phen­yl)imino­meth­yl]pyridine} monohydrate

Kose, M.; McKee, V.

doi:10.1107/S1600536811045399

organic compounds

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Volume 67| Part 12| December 2011| Page o3193

https://doi.org/10.1107/S1600536811045399

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Bis{2,6-bis[(2-hydroxy-5-methylphenyl)iminomethyl]pyridine} monohydrate

Muhammet Kose ^a ^* and Vickie McKee ^a

^aDepartment of Chemistry, Loughborough University, Loughborough LE11 3TU, England
^*Correspondence e-mail: m.kose@lboro.ac.uk

(Received 30 September 2011; accepted 28 October 2011; online 5 November 2011)

The title compound, 2C₂₁H₁₉N₃O₂·H₂O, was synthesized by a Schiff base condensation of 2,6-diformylpyridine with 2-amino-4-methylphenol in ethanol. In the crystal, two molecules of 2,6-bis[(2-hydroxy-5-methylphenyl)iminomethyl]pyridine dimerize via hydrogen bonding to a water molecule, which lies on a twofold axis. There are also intramolecular phenol–imine hydrogen bonds. The dimers are further linked via π–π (phenyl–pyridine) [centroid–centroid distance = 3.707 (2) Å] and π–π edge-to-edge [3.392 (2) Å] interactions. The dihedral angles between the central ring and the two pendant rings are 11.46 (8) and 2.06 (8)° while the pendant rings make a dihedral angle of 10.14 (8)°.

Related literature

For related structures, see: Gonzalez et al. (2008 ); Sun et al. (2006 ).

Experimental

Crystal data

2C₂₁H₁₉N₃O₂·H₂O
M_r = 708.80
Monoclinic, C 2/c
a = 23.8510 (13) Å
b = 12.9688 (7) Å
c = 12.3835 (7) Å
β = 114.077 (1)°
V = 3497.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.60 × 0.28 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ) T_min = 0.947, T_max = 0.991
19364 measured reflections
5005 independent reflections
3919 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.124
S = 1.06
5005 reflections
251 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3	0.836 (17)	1.960 (17)	2.7592 (12)	159.6 (15)
O2—H2A⋯N3	0.836 (17)	2.347 (15)	2.7624 (12)	111.3 (12)
O1—H1A⋯N1	0.86 (2)	2.120 (19)	2.6722 (13)	121.7 (16)
O3—H3D⋯N2	0.812 (16)	2.187 (16)	2.9865 (12)	168.0 (16)
O3—H3D⋯N3	0.812 (16)	2.569 (16)	3.0142 (9)	115.9 (14)

Data collection: APEX2 (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811045399/aa2032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045399/aa2032Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811045399/aa2032Isup3.cml

checkCIF report

Comment top

The molecules crystallize as dimers, assembled by hydrogen bonding around a water molecule. The water molecule sits on a twofold axis and makes four strong hydrogen bonds, as donor to the pyridine nitrogen atoms, and as acceptor from the phenol groups (Table 1). There are also weaker hydrogen bond interactions with one of the imine nitrogen atoms of each molecule. Additionally, there are phenol-imine intramolecular hydrogen bonds in each molecule. The azomethine (C8═N1 and C14═N3) linkage distances are 1.278 (14) and 1.273 (14) Å respectively and within the normal C═N values.

The geometry is cis at the C8═N1 imine group and trans at C14═N3 group. The molecule is close to planar with interplanar angles between the pyridine and phenol groups, 11.46 (8)° and 2.06 (8)° for the rings containing O1 and O2 respectively.

The hydrogen bond geometry at the water molecule is approximately tetrahedral but the angle between the two H-bonded Schiff base molecules is not close to the ideal 90°; the angle between the N2/O3/O2 plane and its equivalent under twofold rotation is 60.52 (4)°. This is possibly a consequence of the intermolecular interactions in the lattice. The Schiff base molecules show two sets of interactions with neighbouring dimeric units. On the more open face (that nearest to the H-bonded phenol of the second molecule), there is a π-π interaction involving the pyridine ring and the phenolimine group H-bonded to central water molecule. The average interplanar distance between this section and its neighbour under symmetry operation 1 - x, -y, -z is 3.354 (1) Å and phenol-pyridine centroid-centroid distance is 3.707 (2) Å. On the other face (partially blocked by the non-bonded phenol of the second molecule), there is a less extensive edge to edge interaction C10 to C11 of a neighbouring dimer under symmetry operation 1 - x, 1 - y, -z is 3.392 (2) Å. These result in columns formed by alternating π-π and edge to edge interactions extending through the lattice.

Related literature top

For related structures, see: Gonzalez et al. (2008); Sun et al. (2006).

Experimental top

A solution of 2,6-diformylpyridine (0.405 g, 3 mmol) in ethanol (15 ml) was added dropwise to an ethanolic solution (30 ml) of 2-amino-4-methylphenol (0.740 g, 6 mmol). A yellow colour appeared and a precipitate was formed in a few minutes. The mixture was stirred for two hours, and then the yellow product was collected by filtration, washed with ethanol-diethylether mixture (1:1) and dried in air. Yield: 0.852 g, 80%, m.p 173–177 C°. Analysis Calc. for C₂₁H₁₉N₃O₂^.0.5(H₂O): C, 71.17; H, 5.69; N, 11.86%. Found: C, 71.03; H, 5.65; N, 11.70%.

Structure description top

For related structures, see: Gonzalez et al. (2008); Sun et al. (2006).

Computing details top

Data collection: APEX2 (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the dimeric compound, thermal ellipsoid 50% probability, hydrogen atoms bonded to carbon atoms are omitted for clarity, hydrogen bonds are shown as dash lines, symmetry operation * 1 - x, y, 1/2 - z.
	Fig. 2. π-π (phenyl-pyridine) and π-π edge to edge interactions in the lattice.

Bis{2,6-bis[(2-hydroxy-5-methylphenyl)iminomethyl]pyridine} monohydrate top

Crystal data top

2C₂₁H₁₉N₃O₂·H₂O	F(000) = 1496
M_r = 708.80	D_x = 1.346 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5957 reflections
a = 23.8510 (13) Å	θ = 2.3–29.8°
b = 12.9688 (7) Å	µ = 0.09 mm⁻¹
c = 12.3835 (7) Å	T = 150 K
β = 114.077 (1)°	Block, yellow
V = 3497.2 (3) Å³	0.60 × 0.28 × 0.11 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5005 independent reflections
Radiation source: fine-focus sealed tube	3919 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 29.8°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −33→33
T_min = 0.947, T_max = 0.991	k = −17→18
19364 measured reflections	l = −17→17

Refinement top

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0642P)² + 1.5272P] where P = (F_o² + 2F_c²)/3
5005 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

2C₂₁H₁₉N₃O₂·H₂O	V = 3497.2 (3) Å³
M_r = 708.80	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 23.8510 (13) Å	µ = 0.09 mm⁻¹
b = 12.9688 (7) Å	T = 150 K
c = 12.3835 (7) Å	0.60 × 0.28 × 0.11 mm
β = 114.077 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5005 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	3919 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.991	R_int = 0.024
19364 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.36 e Å⁻³
5005 reflections	Δρ_min = −0.23 e Å⁻³
251 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.33231 (5)	0.57957 (7)	0.14787 (9)	0.0363 (2)
H1A	0.3535 (9)	0.5552 (15)	0.1120 (17)	0.054*
C1	0.32840 (6)	0.50007 (9)	0.21682 (10)	0.0263 (2)
C2	0.29313 (6)	0.51152 (9)	0.28174 (11)	0.0295 (3)
H2	0.2724	0.5747	0.2792	0.035*
C3	0.28826 (5)	0.43063 (9)	0.35006 (11)	0.0285 (2)
H3	0.2641	0.4391	0.3944	0.034*
C4	0.31806 (5)	0.33642 (9)	0.35549 (10)	0.0259 (2)
C5	0.30934 (6)	0.24734 (10)	0.42542 (12)	0.0344 (3)
H5A	0.3220	0.1832	0.4000	0.052*
H5B	0.2660	0.2426	0.4119	0.052*
H5C	0.3344	0.2584	0.5098	0.052*
C6	0.35360 (5)	0.32612 (9)	0.29095 (10)	0.0243 (2)
H6	0.3744	0.2630	0.2942	0.029*
C7	0.35935 (5)	0.40707 (9)	0.22099 (9)	0.0232 (2)
N1	0.39157 (5)	0.40486 (7)	0.14721 (8)	0.0250 (2)
C8	0.42258 (5)	0.32597 (9)	0.14243 (9)	0.0231 (2)
H8	0.4261	0.2691	0.1931	0.028*
C9	0.45300 (5)	0.32110 (8)	0.06030 (9)	0.0209 (2)
C10	0.44553 (5)	0.39831 (9)	−0.02331 (10)	0.0250 (2)
H10	0.4218	0.4580	−0.0268	0.030*
C11	0.47345 (6)	0.38588 (9)	−0.10081 (10)	0.0274 (2)
H11	0.4695	0.4372	−0.1582	0.033*
C12	0.50726 (5)	0.29722 (9)	−0.09334 (10)	0.0251 (2)
H12	0.5265	0.2866	−0.1461	0.030*
C13	0.51268 (5)	0.22380 (8)	−0.00723 (9)	0.0205 (2)
N2	0.48638 (4)	0.23536 (7)	0.06979 (8)	0.02020 (19)
C14	0.54842 (5)	0.12966 (8)	−0.00076 (9)	0.0219 (2)
H14	0.5582	0.1125	−0.0657	0.026*
N3	0.56667 (4)	0.07051 (7)	0.08909 (8)	0.02191 (19)
C15	0.60324 (5)	−0.01660 (8)	0.09325 (9)	0.0199 (2)
C16	0.63466 (5)	−0.03133 (8)	0.02040 (9)	0.0210 (2)
H16	0.6319	0.0200	−0.0362	0.025*
C17	0.66968 (5)	−0.11873 (8)	0.02855 (9)	0.0218 (2)
C18	0.70282 (5)	−0.13137 (9)	−0.05144 (10)	0.0276 (2)
H18A	0.6833	−0.0877	−0.1215	0.041*
H18B	0.7008	−0.2036	−0.0758	0.041*
H18C	0.7459	−0.1109	−0.0090	0.041*
C19	0.67339 (5)	−0.19289 (8)	0.11334 (10)	0.0242 (2)
H19	0.6969	−0.2536	0.1200	0.029*
C20	0.64359 (5)	−0.17978 (9)	0.18780 (10)	0.0240 (2)
H20	0.6471	−0.2309	0.2452	0.029*
C21	0.60848 (5)	−0.09168 (8)	0.17862 (9)	0.0212 (2)
O2	0.57884 (4)	−0.08313 (7)	0.25167 (7)	0.02766 (19)
H2A	0.5591 (7)	−0.0281 (13)	0.2415 (13)	0.033*
O3	0.5000	0.07316 (9)	0.2500	0.0278 (3)
H3D	0.4959 (8)	0.1100 (13)	0.1942 (14)	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0520 (6)	0.0268 (4)	0.0359 (5)	0.0110 (4)	0.0239 (4)	0.0038 (4)
C1	0.0301 (6)	0.0243 (5)	0.0224 (5)	0.0038 (4)	0.0088 (4)	−0.0028 (4)
C2	0.0304 (6)	0.0275 (6)	0.0300 (6)	0.0074 (5)	0.0119 (5)	−0.0056 (5)
C3	0.0263 (5)	0.0334 (6)	0.0272 (6)	0.0027 (5)	0.0122 (5)	−0.0071 (5)
C4	0.0242 (5)	0.0290 (6)	0.0251 (5)	0.0010 (4)	0.0106 (4)	−0.0033 (4)
C5	0.0364 (7)	0.0364 (7)	0.0386 (7)	0.0026 (5)	0.0236 (6)	0.0021 (5)
C6	0.0242 (5)	0.0247 (5)	0.0241 (5)	0.0043 (4)	0.0099 (4)	−0.0023 (4)
C7	0.0237 (5)	0.0249 (5)	0.0205 (5)	0.0026 (4)	0.0084 (4)	−0.0036 (4)
N1	0.0278 (5)	0.0258 (5)	0.0226 (5)	0.0032 (4)	0.0115 (4)	−0.0022 (4)
C8	0.0235 (5)	0.0252 (5)	0.0210 (5)	0.0021 (4)	0.0097 (4)	−0.0007 (4)
C9	0.0203 (5)	0.0229 (5)	0.0193 (5)	0.0002 (4)	0.0077 (4)	−0.0021 (4)
C10	0.0268 (5)	0.0223 (5)	0.0249 (5)	0.0021 (4)	0.0098 (4)	0.0009 (4)
C11	0.0315 (6)	0.0270 (5)	0.0241 (5)	0.0007 (4)	0.0117 (5)	0.0056 (4)
C12	0.0270 (5)	0.0302 (6)	0.0199 (5)	0.0012 (4)	0.0115 (4)	0.0021 (4)
C13	0.0207 (5)	0.0242 (5)	0.0168 (4)	0.0003 (4)	0.0079 (4)	−0.0007 (4)
N2	0.0205 (4)	0.0226 (4)	0.0182 (4)	0.0003 (3)	0.0086 (3)	−0.0012 (3)
C14	0.0232 (5)	0.0267 (5)	0.0185 (5)	0.0021 (4)	0.0110 (4)	−0.0009 (4)
N3	0.0248 (4)	0.0221 (4)	0.0224 (4)	0.0006 (3)	0.0133 (4)	−0.0004 (3)
C15	0.0224 (5)	0.0201 (5)	0.0182 (5)	0.0001 (4)	0.0093 (4)	−0.0011 (4)
C16	0.0231 (5)	0.0215 (5)	0.0203 (5)	0.0003 (4)	0.0109 (4)	0.0008 (4)
C17	0.0217 (5)	0.0225 (5)	0.0223 (5)	−0.0011 (4)	0.0102 (4)	−0.0031 (4)
C18	0.0295 (6)	0.0278 (6)	0.0307 (6)	0.0032 (5)	0.0176 (5)	−0.0011 (4)
C19	0.0235 (5)	0.0218 (5)	0.0268 (5)	0.0022 (4)	0.0097 (4)	0.0000 (4)
C20	0.0263 (5)	0.0232 (5)	0.0215 (5)	−0.0003 (4)	0.0086 (4)	0.0034 (4)
C21	0.0230 (5)	0.0246 (5)	0.0171 (5)	−0.0023 (4)	0.0093 (4)	−0.0008 (4)
O2	0.0370 (5)	0.0287 (4)	0.0239 (4)	0.0042 (4)	0.0191 (4)	0.0038 (3)
O3	0.0386 (7)	0.0270 (6)	0.0266 (6)	0.000	0.0223 (5)	0.000

Geometric parameters (Å, º) top

O1—C1	1.3660 (15)	C11—H11	0.9500
O1—H1A	0.86 (2)	C12—C13	1.3957 (15)
C1—C2	1.3884 (16)	C12—H12	0.9500
C1—C7	1.4040 (15)	C13—N2	1.3467 (13)
C2—C3	1.3821 (18)	C13—C14	1.4725 (15)
C2—H2	0.9500	C14—N3	1.2731 (14)
C3—C4	1.4012 (16)	C14—H14	0.9500
C3—H3	0.9500	N3—C15	1.4153 (13)
C4—C6	1.3885 (15)	C15—C16	1.4013 (14)
C4—C5	1.5083 (17)	C15—C21	1.4048 (14)
C5—H5A	0.9800	C16—C17	1.3870 (15)
C5—H5B	0.9800	C16—H16	0.9500
C5—H5C	0.9800	C17—C19	1.3998 (15)
C6—C7	1.4030 (16)	C17—C18	1.5072 (15)
C6—H6	0.9500	C18—H18A	0.9800
C7—N1	1.4139 (14)	C18—H18B	0.9800
N1—C8	1.2778 (14)	C18—H18C	0.9800
C8—C9	1.4721 (15)	C19—C20	1.3853 (15)
C8—H8	0.9500	C19—H19	0.9500
C9—N2	1.3445 (14)	C20—C21	1.3934 (15)
C9—C10	1.3985 (15)	C20—H20	0.9500
C10—C11	1.3827 (16)	C21—O2	1.3610 (13)
C10—H10	0.9500	O2—H2A	0.836 (17)
C11—C12	1.3857 (16)	O3—H3D	0.812 (16)

C1—O1—H1A	104.5 (13)	C12—C11—H11	120.6
O1—C1—C2	119.56 (10)	C11—C12—C13	119.14 (10)
O1—C1—C7	120.15 (10)	C11—C12—H12	120.4
C2—C1—C7	120.28 (11)	C13—C12—H12	120.4
C3—C2—C1	119.70 (10)	N2—C13—C12	122.72 (10)
C3—C2—H2	120.2	N2—C13—C14	118.71 (9)
C1—C2—H2	120.2	C12—C13—C14	118.57 (9)
C2—C3—C4	121.56 (11)	C9—N2—C13	117.41 (9)
C2—C3—H3	119.2	N3—C14—C13	122.07 (9)
C4—C3—H3	119.2	N3—C14—H14	119.0
C6—C4—C3	118.25 (11)	C13—C14—H14	119.0
C6—C4—C5	121.09 (10)	C14—N3—C15	119.91 (9)
C3—C4—C5	120.61 (10)	C16—C15—C21	118.89 (9)
C4—C5—H5A	109.5	C16—C15—N3	124.68 (9)
C4—C5—H5B	109.5	C21—C15—N3	116.42 (9)
H5A—C5—H5B	109.5	C17—C16—C15	121.93 (10)
C4—C5—H5C	109.5	C17—C16—H16	119.0
H5A—C5—H5C	109.5	C15—C16—H16	119.0
H5B—C5—H5C	109.5	C16—C17—C19	117.90 (10)
C4—C6—C7	121.31 (10)	C16—C17—C18	120.18 (10)
C4—C6—H6	119.3	C19—C17—C18	121.92 (10)
C7—C6—H6	119.3	C17—C18—H18A	109.5
C6—C7—C1	118.89 (10)	C17—C18—H18B	109.5
C6—C7—N1	126.84 (10)	H18A—C18—H18B	109.5
C1—C7—N1	114.20 (10)	C17—C18—H18C	109.5
C8—N1—C7	121.58 (10)	H18A—C18—H18C	109.5
N1—C8—C9	121.61 (10)	H18B—C18—H18C	109.5
N1—C8—H8	119.2	C20—C19—C17	121.49 (10)
C9—C8—H8	119.2	C20—C19—H19	119.3
N2—C9—C10	123.29 (10)	C17—C19—H19	119.3
N2—C9—C8	114.60 (9)	C19—C20—C21	120.05 (10)
C10—C9—C8	122.07 (10)	C19—C20—H20	120.0
C11—C10—C9	118.58 (10)	C21—C20—H20	120.0
C11—C10—H10	120.7	O2—C21—C20	118.06 (9)
C9—C10—H10	120.7	O2—C21—C15	122.20 (10)
C10—C11—C12	118.84 (10)	C20—C21—C15	119.72 (9)
C10—C11—H11	120.6	C21—O2—H2A	112.5 (10)

O1—C1—C2—C3	178.93 (11)	C11—C12—C13—C14	179.63 (10)
C7—C1—C2—C3	−0.42 (18)	C10—C9—N2—C13	−1.22 (16)
C1—C2—C3—C4	−0.16 (18)	C8—C9—N2—C13	176.55 (9)
C2—C3—C4—C6	0.66 (18)	C12—C13—N2—C9	1.05 (15)
C2—C3—C4—C5	−176.69 (12)	C14—C13—N2—C9	−178.70 (9)
C3—C4—C6—C7	−0.61 (17)	N2—C13—C14—N3	−15.80 (16)
C5—C4—C6—C7	176.73 (11)	C12—C13—C14—N3	164.44 (11)
C4—C6—C7—C1	0.06 (17)	C13—C14—N3—C15	−177.17 (9)
C4—C6—C7—N1	−176.84 (11)	C14—N3—C15—C16	16.85 (16)
O1—C1—C7—C6	−178.88 (10)	C14—N3—C15—C21	−164.27 (10)
C2—C1—C7—C6	0.47 (17)	C21—C15—C16—C17	1.35 (16)
O1—C1—C7—N1	−1.61 (16)	N3—C15—C16—C17	−179.79 (10)
C2—C1—C7—N1	177.74 (10)	C15—C16—C17—C19	−0.49 (16)
C6—C7—N1—C8	−3.83 (18)	C15—C16—C17—C18	−179.90 (10)
C1—C7—N1—C8	179.15 (10)	C16—C17—C19—C20	−0.50 (16)
C7—N1—C8—C9	176.17 (10)	C18—C17—C19—C20	178.90 (10)
N1—C8—C9—N2	176.83 (10)	C17—C19—C20—C21	0.60 (17)
N1—C8—C9—C10	−5.37 (17)	C19—C20—C21—O2	178.48 (10)
N2—C9—C10—C11	0.45 (17)	C19—C20—C21—C15	0.29 (16)
C8—C9—C10—C11	−177.16 (10)	C16—C15—C21—O2	−179.34 (10)
C9—C10—C11—C12	0.52 (17)	N3—C15—C21—O2	1.71 (15)
C10—C11—C12—C13	−0.68 (17)	C16—C15—C21—C20	−1.24 (15)
C11—C12—C13—N2	−0.12 (17)	N3—C15—C21—C20	179.82 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.836 (17)	1.960 (17)	2.7592 (12)	159.6 (15)
O2—H2A···N3	0.836 (17)	2.347 (15)	2.7624 (12)	111.3 (12)
O1—H1A···N1	0.86 (2)	2.120 (19)	2.6722 (13)	121.7 (16)
O3—H3D···N2	0.812 (16)	2.187 (16)	2.9865 (12)	168.0 (16)
O3—H3D···N3	0.812 (16)	2.569 (16)	3.0142 (9)	115.9 (14)

Experimental details

Crystal data
Chemical formula	2C₂₁H₁₉N₃O₂·H₂O
M_r	708.80
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	23.8510 (13), 12.9688 (7), 12.3835 (7)
β (°)	114.077 (1)
V (Å³)	3497.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.28 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.947, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	19364, 5005, 3919
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.700

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.124, 1.06
No. of reflections	5005
No. of parameters	251
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.23

Computer programs: APEX2 (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.836 (17)	1.960 (17)	2.7592 (12)	159.6 (15)
O2—H2A···N3	0.836 (17)	2.347 (15)	2.7624 (12)	111.3 (12)
O1—H1A···N1	0.86 (2)	2.120 (19)	2.6722 (13)	121.7 (16)
O3—H3D···N2	0.812 (16)	2.187 (16)	2.9865 (12)	168.0 (16)
O3—H3D···N3	0.812 (16)	2.569 (16)	3.0142 (9)	115.9 (14)

Acknowledgements

We are grateful to the Turkish Government for the award of a postgraduate scholarship (to MK)

References

Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gonzalez, A., Gomez, E., Cortes-Lozada, A., Hernandez, S., Ramirez-Apan, T. & Nieto-Camacho, A. (2008). Chem. Pharm. Bull. 57, 5–15. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, X. X., Qi, C. M., Ma, S. L., Huang, H. B., Zhu, W. & Liu, Y. C. (2006). Inorg. Chem. Commun. 9, 911–914. Web of Science CSD CrossRef CAS Google Scholar