organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2,2′-{[2-(Pyridin-2-yl)-1,3-diazinane-1,3-diyl]bis­(methylene)}diphenol

aDepto. de Química, Universidade Federal de Santa Catarina, 88040-900 - Florianópolis, SC, Brazil
*Correspondence e-mail: adailton.bortoluzzi@ufsc.br

(Received 25 July 2012; accepted 10 August 2012; online 23 August 2012)

The title compound, C23H25N3O2, was obtained as an inter­mediary in the preparation of non-symmetric tertiary diamines. The mol­ecular structure presents T-shaped spatial form, in which the pyrimidine ring exhibits a chair conformation. The pyridyl ring is almost perpendicular to the phenyl rings with dihedral angles of 80.17 (8) and 76.03 (2)°. The phenol and amine groups are involved in two strong intra­molecular O—H⋯N inter­actions. In the crystal, the mol­ecules are stacked along [010]; however, no inter­molecular inter­actions are observed.

Related literature

For the synthetic procedure, see: Hureau et al. (2008[Hureau, C., Groni, S., Guillot, R., Blondin, G., Duboc, C. & Anxolabehere-Mallart, E. (2008). Inorg. Chem. 47, 9238-9247.]). For related structures, see: Yokoyama et al. (1995[Yokoyama, T., Etoh, N. & Zenki, M. (1995). Anal. Sci. 11, 875-876.]); Xia et al. (2007[Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Gao, W. (2007). Acta Cryst. E63, o3665.]). For standard bond lengths and angles, see: Bruno et al. (2004[Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004). J. Chem. Inf. Comput. Sci. 44, 2133-2144.]).

[Scheme 1]

Experimental

Crystal data
  • C23H25N3O2

  • Mr = 375.46

  • Monoclinic, P 21 /n

  • a = 18.7615 (16) Å

  • b = 6.2105 (11) Å

  • c = 19.0407 (12) Å

  • β = 114.594 (8)°

  • V = 2017.3 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.50 × 0.50 × 0.40 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • 3711 measured reflections

  • 3595 independent reflections

  • 2038 reflections with I > 2σ(I)

  • Rint = 0.079

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.146

  • S = 1.01

  • 3595 reflections

  • 253 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O10—H10⋯N1 1.02 1.69 2.624 (3) 150
O20—H20⋯N5 1.09 1.72 2.705 (3) 148

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: SET4 in CAD-4 Software; data reduction: HELENA (Spek, 1996[Spek, A. L. (1996). HELENA. University of Utrecht, The Netherlands.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The molecular structure of the title compound (I) shows T-shaped spatial form (Fig. 1). Pyrimidine ring adopts regular chair conformation with square plane formed by N1/C2/C4/C5 atoms (r.m.s. deviation = 0.0111).

The dihedral angles between the mean planes of the rings C31/C36 and C11/C16 of 80.17 (8)° and C31/36 and C211/C26 of 76.03 (8)° demonstrate that pyridil ring is almost perpendicular to phenol groups.

Two strong intramolecular O—H···N hydrogen bonds between phenol and amine groups (Table 1) form additional six-membered rings, which contribute for the rigidity of the structure and avoid the crystal supramolecurity.

The molecules are stacked along [010] direction, however no further intermolecular interactions, such as π-stacking, were observed.

All bond lengths and angles found for (I) are in the expected range for organic compounds (Bruno et al., 2004).

Related literature top

For the synthetic procedure, see: Hureau et al. (2008). For related structures, see: Yokoyama et al. (1995); Xia et al. (2007). For standard bond lengths and angles, see: Bruno et al. (2004).

Experimental top

Compound (I) was synthesized according to the procedure described by Hureau et al. (2008).

A solution containing 6.0 g of N,N'-bis(2-hydroxybenzyl)-1,3-diamino-propane (21,3 mmol) and 2.39 g (21,3 mmol) of 2-pyridinecarboxaldehyde in 60 ml of MeOH was stirred at temperature of 333,15 K for 1 h. The solvent was evaporated under reduced pressure to afford a white precipitate, which was filtered off and washed with dry diethyl eter. (85% yield = 85%). MP 154.6–154.9 °C, EA for C23H25N3O2: calc C 73,53%; H 7,18%; N 11,27%, found C, 73.57%; H, 6.71%; N, 11.195.

Refinement top

H atoms attached to carbon atoms were placed at their idealized positions with distances of 0.98 and 0.97 Å and Uiso fixed at 1.2 times of Ueq of the preceding atom for CH and CH2, respectively. H atoms of the hydroxyl groups were found from difference map and treated with riding model and their Uiso were fixed at 1.2 times of Ueq of the parent atom.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: SET4 in CAD-4 Software (Enraf–Nonius, 1989); data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
Figure 1. The molecular structure of the title compound. Ellipsoids are shown at the 40% probability level.
2,2'-{[2-(Pyridin-2-yl)-1,3-diazinane-1,3-diyl]bis(methylene)}diphenol top
Crystal data top
C23H25N3O2F(000) = 800
Mr = 375.46Dx = 1.236 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 18.7615 (16) Åθ = 5.5–17.4°
b = 6.2105 (11) ŵ = 0.08 mm1
c = 19.0407 (12) ÅT = 293 K
β = 114.594 (8)°Block, colorless
V = 2017.3 (4) Å30.50 × 0.50 × 0.40 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.079
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 1.3°
Graphite monochromatorh = 2022
ω–2θ scansk = 70
3711 measured reflectionsl = 220
3595 independent reflections3 standard reflections every 200 reflections
2038 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0711P)2 + 0.2051P]
where P = (Fo2 + 2Fc2)/3
3595 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C23H25N3O2V = 2017.3 (4) Å3
Mr = 375.46Z = 4
Monoclinic, P21/nMo Kα radiation
a = 18.7615 (16) ŵ = 0.08 mm1
b = 6.2105 (11) ÅT = 293 K
c = 19.0407 (12) Å0.50 × 0.50 × 0.40 mm
β = 114.594 (8)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.079
3711 measured reflections3 standard reflections every 200 reflections
3595 independent reflections intensity decay: 1%
2038 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.01Δρmax = 0.17 e Å3
3595 reflectionsΔρmin = 0.21 e Å3
253 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.65802 (10)0.2353 (3)0.10455 (10)0.0445 (5)
C20.57867 (13)0.1394 (4)0.14032 (13)0.0545 (7)
H2A0.58280.01300.14920.065*
H2B0.54880.20730.18980.065*
C30.53699 (14)0.1696 (5)0.08857 (14)0.0636 (8)
H3A0.52850.32180.08350.076*
H3B0.48630.09890.11090.076*
C40.58552 (14)0.0754 (5)0.01042 (14)0.0631 (8)
H4A0.55940.09820.02350.076*
H4B0.59140.07840.01510.076*
N50.66299 (10)0.1781 (3)0.02244 (11)0.0481 (5)
C100.69848 (14)0.2035 (4)0.15583 (14)0.0528 (6)
H10A0.69640.05210.16910.063*
H10B0.75320.24330.12830.063*
C110.66255 (14)0.3345 (4)0.22904 (13)0.0504 (6)
C120.63385 (15)0.5401 (4)0.22823 (15)0.0581 (7)
C130.60453 (16)0.6654 (5)0.29458 (16)0.0697 (8)
H130.58380.80090.29380.084*
C140.60633 (17)0.5889 (6)0.36109 (17)0.0781 (9)
H140.58810.67470.40510.094*
C150.63473 (17)0.3875 (6)0.36363 (16)0.0741 (9)
H150.63530.33610.40930.089*
C160.66272 (15)0.2605 (5)0.29765 (15)0.0635 (7)
H160.68190.12350.29950.076*
C200.70860 (14)0.0956 (4)0.10175 (13)0.0536 (7)
H20A0.76140.15320.12140.064*
H20B0.71210.06000.10000.064*
C210.67202 (13)0.1560 (4)0.15583 (13)0.0479 (6)
C220.64091 (15)0.3595 (5)0.15448 (14)0.0564 (7)
C230.61059 (16)0.4140 (5)0.20724 (16)0.0689 (8)
H230.58920.55000.20570.083*
C240.61217 (17)0.2666 (6)0.26183 (16)0.0735 (8)
H240.59210.30380.29740.088*
C250.64312 (17)0.0652 (5)0.26416 (15)0.0703 (8)
H250.64430.03410.30120.084*
C260.67240 (14)0.0119 (4)0.21108 (13)0.0568 (7)
H260.69300.12500.21250.068*
C300.70474 (12)0.1435 (4)0.02717 (12)0.0443 (6)
H300.71150.01140.03210.053*
C310.78452 (13)0.2502 (4)0.00853 (13)0.0451 (6)
N320.84615 (11)0.1185 (3)0.03432 (12)0.0549 (6)
C330.91701 (15)0.2096 (5)0.06679 (17)0.0691 (8)
H330.96050.11950.08610.083*
C340.92949 (17)0.4257 (6)0.07337 (17)0.0740 (9)
H340.98010.48100.09550.089*
C350.86581 (17)0.5606 (5)0.04665 (14)0.0638 (8)
H350.87230.70920.05050.077*
C360.79262 (15)0.4714 (4)0.01433 (14)0.0550 (7)
H360.74850.55920.00370.066*
O100.63242 (12)0.6251 (3)0.16299 (11)0.0789 (6)
H100.64850.50270.12400.095*
O200.63844 (12)0.5107 (3)0.10137 (11)0.0754 (6)
H200.65310.42370.05970.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0433 (11)0.0465 (11)0.0424 (10)0.0008 (9)0.0167 (9)0.0002 (9)
C20.0463 (14)0.0617 (17)0.0479 (13)0.0021 (13)0.0120 (11)0.0025 (13)
C30.0396 (13)0.093 (2)0.0531 (15)0.0052 (14)0.0141 (12)0.0054 (15)
C40.0490 (15)0.084 (2)0.0529 (15)0.0118 (14)0.0176 (12)0.0097 (15)
N50.0394 (11)0.0558 (13)0.0452 (11)0.0027 (10)0.0136 (9)0.0079 (10)
C100.0543 (15)0.0494 (15)0.0565 (15)0.0046 (12)0.0249 (13)0.0022 (12)
C110.0479 (14)0.0565 (16)0.0476 (14)0.0053 (12)0.0206 (11)0.0021 (13)
C120.0621 (17)0.0532 (16)0.0529 (16)0.0021 (14)0.0178 (13)0.0038 (14)
C130.0732 (19)0.0683 (19)0.0600 (17)0.0021 (16)0.0202 (15)0.0139 (16)
C140.069 (2)0.100 (3)0.0585 (19)0.0141 (19)0.0190 (15)0.0212 (19)
C150.0710 (19)0.108 (3)0.0508 (17)0.022 (2)0.0330 (15)0.0036 (18)
C160.0602 (16)0.078 (2)0.0611 (17)0.0102 (15)0.0337 (14)0.0119 (16)
C200.0468 (14)0.0567 (16)0.0479 (14)0.0035 (12)0.0104 (11)0.0101 (13)
C210.0412 (13)0.0541 (15)0.0392 (13)0.0039 (12)0.0076 (10)0.0041 (12)
C220.0530 (15)0.0593 (17)0.0517 (15)0.0035 (14)0.0167 (12)0.0081 (14)
C230.0653 (18)0.073 (2)0.0637 (17)0.0132 (16)0.0224 (15)0.0025 (16)
C240.074 (2)0.094 (2)0.0539 (17)0.0093 (19)0.0283 (15)0.0021 (18)
C250.0755 (19)0.085 (2)0.0472 (15)0.0029 (18)0.0225 (14)0.0134 (16)
C260.0556 (15)0.0609 (17)0.0450 (14)0.0030 (13)0.0121 (12)0.0065 (13)
C300.0408 (13)0.0365 (12)0.0505 (14)0.0009 (11)0.0140 (11)0.0029 (11)
C310.0461 (14)0.0459 (15)0.0437 (13)0.0016 (12)0.0191 (11)0.0029 (12)
N320.0421 (12)0.0536 (13)0.0643 (13)0.0055 (11)0.0176 (10)0.0002 (11)
C330.0424 (16)0.077 (2)0.078 (2)0.0063 (15)0.0156 (14)0.0024 (17)
C340.0540 (17)0.093 (3)0.0694 (19)0.0226 (18)0.0199 (15)0.0098 (18)
C350.076 (2)0.0546 (17)0.0557 (16)0.0227 (16)0.0219 (15)0.0059 (14)
C360.0592 (17)0.0457 (16)0.0567 (15)0.0011 (13)0.0207 (13)0.0039 (13)
O100.1205 (17)0.0512 (12)0.0618 (12)0.0213 (12)0.0346 (12)0.0043 (10)
O200.0978 (15)0.0595 (12)0.0769 (13)0.0172 (11)0.0444 (11)0.0199 (11)
Geometric parameters (Å, º) top
N1—C101.478 (3)C20—C211.504 (3)
N1—C301.480 (3)C20—H20A0.9700
N1—C21.480 (3)C20—H20B0.9700
C2—C31.503 (3)C21—C261.379 (3)
C2—H2A0.9700C21—C221.388 (4)
C2—H2B0.9700C22—O201.367 (3)
C3—C41.503 (3)C22—C231.387 (4)
C3—H3A0.9700C23—C241.376 (4)
C3—H3B0.9700C23—H230.9300
C4—N51.468 (3)C24—C251.372 (4)
C4—H4A0.9700C24—H240.9300
C4—H4B0.9700C25—C261.376 (4)
N5—C301.472 (3)C25—H250.9300
N5—C201.483 (3)C26—H260.9300
C10—C111.509 (3)C30—C311.515 (3)
C10—H10A0.9700C30—H300.9800
C10—H10B0.9700C31—N321.332 (3)
C11—C161.386 (3)C31—C361.382 (3)
C11—C121.388 (4)N32—C331.336 (3)
C12—O101.360 (3)C33—C341.359 (4)
C12—C131.388 (4)C33—H330.9300
C13—C141.366 (4)C34—C351.372 (4)
C13—H130.9300C34—H340.9300
C14—C151.368 (4)C35—C361.367 (3)
C14—H140.9300C35—H350.9300
C15—C161.388 (4)C36—H360.9300
C15—H150.9300O10—H101.0163
C16—H160.9300O20—H201.0857
C10—N1—C30110.60 (17)N5—C20—C21112.13 (19)
C10—N1—C2109.68 (18)N5—C20—H20A109.2
C30—N1—C2111.63 (18)C21—C20—H20A109.2
N1—C2—C3110.3 (2)N5—C20—H20B109.2
N1—C2—H2A109.6C21—C20—H20B109.2
C3—C2—H2A109.6H20A—C20—H20B107.9
N1—C2—H2B109.6C26—C21—C22118.3 (2)
C3—C2—H2B109.6C26—C21—C20120.1 (2)
H2A—C2—H2B108.1C22—C21—C20121.5 (2)
C4—C3—C2109.6 (2)O20—C22—C23118.1 (3)
C4—C3—H3A109.8O20—C22—C21121.6 (2)
C2—C3—H3A109.8C23—C22—C21120.3 (3)
C4—C3—H3B109.8C24—C23—C22119.9 (3)
C2—C3—H3B109.8C24—C23—H23120.0
H3A—C3—H3B108.2C22—C23—H23120.0
N5—C4—C3109.7 (2)C25—C24—C23120.4 (3)
N5—C4—H4A109.7C25—C24—H24119.8
C3—C4—H4A109.7C23—C24—H24119.8
N5—C4—H4B109.7C24—C25—C26119.2 (3)
C3—C4—H4B109.7C24—C25—H25120.4
H4A—C4—H4B108.2C26—C25—H25120.4
C4—N5—C30111.11 (18)C25—C26—C21121.8 (3)
C4—N5—C20109.47 (18)C25—C26—H26119.1
C30—N5—C20111.56 (18)C21—C26—H26119.1
N1—C10—C11112.53 (19)N5—C30—N1109.26 (17)
N1—C10—H10A109.1N5—C30—C31109.79 (18)
C11—C10—H10A109.1N1—C30—C31110.09 (18)
N1—C10—H10B109.1N5—C30—H30109.2
C11—C10—H10B109.1N1—C30—H30109.2
H10A—C10—H10B107.8C31—C30—H30109.2
C16—C11—C12117.9 (2)N32—C31—C36122.1 (2)
C16—C11—C10121.1 (2)N32—C31—C30116.2 (2)
C12—C11—C10120.8 (2)C36—C31—C30121.7 (2)
O10—C12—C13117.6 (3)C31—N32—C33117.1 (2)
O10—C12—C11121.5 (2)N32—C33—C34124.1 (3)
C13—C12—C11120.9 (3)N32—C33—H33118.0
C14—C13—C12119.7 (3)C34—C33—H33118.0
C14—C13—H13120.1C33—C34—C35118.6 (3)
C12—C13—H13120.1C33—C34—H34120.7
C13—C14—C15120.7 (3)C35—C34—H34120.7
C13—C14—H14119.6C36—C35—C34118.4 (3)
C15—C14—H14119.6C36—C35—H35120.8
C14—C15—C16119.6 (3)C34—C35—H35120.8
C14—C15—H15120.2C35—C36—C31119.7 (3)
C16—C15—H15120.2C35—C36—H36120.1
C11—C16—C15121.1 (3)C31—C36—H36120.1
C11—C16—H16119.5C12—O10—H10105.3
C15—C16—H16119.5C22—O20—H20104.9
C10—N1—C2—C3179.7 (2)C20—C21—C22—C23177.2 (2)
C30—N1—C2—C356.7 (3)O20—C22—C23—C24179.8 (3)
N1—C2—C3—C456.0 (3)C21—C22—C23—C240.8 (4)
C2—C3—C4—N557.8 (3)C22—C23—C24—C250.4 (4)
C3—C4—N5—C3060.3 (3)C23—C24—C25—C260.2 (4)
C3—C4—N5—C20176.1 (2)C24—C25—C26—C210.5 (4)
C30—N1—C10—C11167.62 (19)C22—C21—C26—C250.1 (4)
C2—N1—C10—C1168.8 (2)C20—C21—C26—C25176.6 (2)
N1—C10—C11—C16148.2 (2)C4—N5—C30—N159.5 (2)
N1—C10—C11—C1236.9 (3)C20—N5—C30—N1178.04 (17)
C16—C11—C12—O10179.3 (2)C4—N5—C30—C31179.67 (19)
C10—C11—C12—O104.3 (4)C20—N5—C30—C3157.2 (2)
C16—C11—C12—C131.5 (4)C10—N1—C30—N5179.92 (18)
C10—C11—C12—C13176.6 (2)C2—N1—C30—N557.7 (2)
O10—C12—C13—C14178.5 (2)C10—N1—C30—C3159.3 (2)
C11—C12—C13—C142.3 (4)C2—N1—C30—C31178.30 (19)
C12—C13—C14—C151.8 (4)N5—C30—C31—N32111.9 (2)
C13—C14—C15—C160.6 (4)N1—C30—C31—N32127.7 (2)
C12—C11—C16—C150.3 (4)N5—C30—C31—C3667.7 (3)
C10—C11—C16—C15175.4 (2)N1—C30—C31—C3652.7 (3)
C14—C15—C16—C110.1 (4)C36—C31—N32—C330.3 (4)
C4—N5—C20—C2164.3 (3)C30—C31—N32—C33179.3 (2)
C30—N5—C20—C21172.29 (19)C31—N32—C33—C341.4 (4)
N5—C20—C21—C26141.8 (2)N32—C33—C34—C351.4 (5)
N5—C20—C21—C2241.6 (3)C33—C34—C35—C360.2 (4)
C26—C21—C22—O20179.9 (2)C34—C35—C36—C310.7 (4)
C20—C21—C22—O203.4 (4)N32—C31—C36—C350.7 (4)
C26—C21—C22—C230.5 (4)C30—C31—C36—C35179.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—H10···N11.021.692.624 (3)150
O20—H20···N51.091.722.705 (3)148

Experimental details

Crystal data
Chemical formulaC23H25N3O2
Mr375.46
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)18.7615 (16), 6.2105 (11), 19.0407 (12)
β (°) 114.594 (8)
V3)2017.3 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.50 × 0.50 × 0.40
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3711, 3595, 2038
Rint0.079
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.146, 1.01
No. of reflections3595
No. of parameters253
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.21

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), SET4 in CAD-4 Software (Enraf–Nonius, 1989), HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—H10···N11.021.692.624 (3)150
O20—H20···N51.091.722.705 (3)148
 

Acknowledgements

The authors thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and the Financiadora de Estudos e Projetos (FINEP) for financial support.

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals
First citationBruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004). J. Chem. Inf. Comput. Sci. 44, 2133–2144.  Web of Science CrossRef PubMed CAS
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.
First citationHureau, C., Groni, S., Guillot, R., Blondin, G., Duboc, C. & Anxolabehere-Mallart, E. (2008). Inorg. Chem. 47, 9238–9247.  Web of Science CSD CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (1996). HELENA. University of Utrecht, The Netherlands.
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationXia, H.-T., Liu, Y.-F., Wang, D.-Q. & Gao, W. (2007). Acta Cryst. E63, o3665.  Web of Science CSD CrossRef IUCr Journals
First citationYokoyama, T., Etoh, N. & Zenki, M. (1995). Anal. Sci. 11, 875–876.  CrossRef CAS Web of Science

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