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Acta Cryst. (2009). E65, o541    [ doi:10.1107/S1600536809004929 ]

2,2'-(1,10-Phenanthrolin-2-ylimino)diethanol

X. Jin and J. M. Li

Abstract top

In the title compound, C16H17N3O2, symmetry-related molecules are linked into one-dimensional chains along the a axis by a combination of intermolecular O-H...N and O-H...O hydrogen bonds and weak [pi]-[pi] stacking interactions with a centroid-centroid distance of 3.5494 (12) Å.

Comment top

Derivatives of 1,10-phenanthroline play a vital role in a modern coordination chemistry and a number of complexes have been published with these types of compounds as ligands [see for example the recent publications by Li et al. (2008) and Zhang et al. (2008)]. An interest in designing new derivatives led to the synthesis the title compound, (I), and its crystal structure is reported herein.

The molecular structure of (I) is shown in Fig. 1. In the crystal structure, intermolecular O—H···N and O—H···O hydrogen bonds (see Table 1) connect symmetry related molecules to form 1-D chains along the a axis (see Fig. 2). In addition, within these chain there are weak π-π stacking interactions between symmetry related pyridyl rings, with the relevant distances being Cg1···Cg2iii = 3.5494 (12) Å, Cg1···Cg2iiiperp = 3.464 Å and α = 1.48° [symmetry code (iii) 1+x, y, z; Cg1 and Cg2 are the centroids of the C6C7C10-C12/N1 and C1—C5/N2 rings, respectively; Cg1···Cg2iiiperp is the perpendicular distance from ring Cg1 to ring Cg2iii; α is the dihedral angle between ring plane Cg1 and ring plane Cg2iii].

Related literature top

For recent crystal structure reports on the complexes formed with derivatives of 1,10-phenanthroline , see for example: Li et al. (2008) and Zhang et al. (2008).

Experimental top

2-Diethanolamine-1,10-phenanthroline (0.0523 g, 0.185 mmol) was dissolved into 10 ml methanol and the yellow single crystals were obtained after the solution had been allowed to stand at room temperature for one week.

Refinement top

The H atoms of hydroxyl groups were found in a difference Fourier map and were included in 'as found' positions with d(O—H) = 0.83 & 0.91 Å; all other H atoms were placed in calculated positions with C—H = 0.93–0.97 Å. All H atoms were refined as riding, with Uiso(H) = 1.5eq(O) for hydroxyl group and Uiso(H) = 1.2Ueq(C) for other groups.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the the atom numbering scheme with thermal ellipsoids drawn at the 30% probability level
[Figure 2] Fig. 2. Part of the crystal structure of (I) showing hydrogen bonds (dashed lines) between symmetry realted molecules which form a one-dimensional chain along the a axis.
2,2'-(1,10-Phenanthrolin-2-ylimino)diethanol top
Crystal data top
C16H17N3O2F(000) = 600
Mr = 283.33Dx = 1.388 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2381 reflections
a = 4.848 (1) Åθ = 2.6–27.3°
b = 14.854 (3) ŵ = 0.09 mm−1
c = 18.858 (4) ÅT = 298 K
β = 93.523 (3)°Block, yellow
V = 1355.5 (5) Å30.54 × 0.32 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		2765 independent reflections
Radiation source: fine-focus sealed tube2149 reflections with I > 2σ(I)
graphiteRint = 0.030
φ and ω scansθmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −5→6
Tmin = 0.951, Tmax = 0.982k = −12→18
7520 measured reflectionsl = −23→23
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0762P)2 + 0.108P]
where P = (Fo2 + 2Fc2)/3
2765 reflections(Δ/σ)max = 0.008
190 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
Crystal data top
C16H17N3O2V = 1355.5 (5) Å3
Mr = 283.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.848 (1) ŵ = 0.09 mm−1
b = 14.854 (3) ÅT = 298 K
c = 18.858 (4) Å0.54 × 0.32 × 0.20 mm
β = 93.523 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer		2765 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2149 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.982Rint = 0.030
7520 measured reflectionsθmax = 26.5°
Refinement top
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.132Δρmax = 0.24 e Å−3
S = 1.02Δρmin = −0.16 e Å−3
2765 reflectionsAbsolute structure: ?
190 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1−0.1483 (3)0.89542 (10)0.18581 (7)0.0333 (3)
C2−0.2322 (3)0.81999 (11)0.22608 (8)0.0408 (4)
H2−0.36970.78140.20770.049*
C3−0.1090 (4)0.80542 (11)0.29126 (8)0.0439 (4)
H3−0.16450.75690.31810.053*
C40.1020 (3)0.86265 (10)0.31895 (8)0.0391 (4)
C50.1770 (3)0.93444 (10)0.27517 (7)0.0336 (3)
C60.3910 (3)0.99566 (10)0.30193 (7)0.0356 (4)
C70.5185 (3)0.98199 (12)0.37060 (8)0.0460 (4)
C80.4363 (4)0.90765 (14)0.41232 (9)0.0597 (5)
H80.52270.89800.45710.072*
C90.2361 (4)0.85156 (13)0.38776 (9)0.0553 (5)
H90.18330.80430.41630.066*
C100.7237 (4)1.04302 (14)0.39446 (10)0.0593 (5)
H100.81221.03620.43930.071*
C110.7935 (4)1.11242 (14)0.35196 (11)0.0598 (5)
H110.92891.15360.36730.072*
C120.6584 (4)1.12040 (12)0.28535 (10)0.0494 (4)
H120.70791.16790.25670.059*
C13−0.1736 (3)0.99054 (11)0.08028 (7)0.0387 (4)
H13A−0.24370.98410.03130.046*
H13B0.02640.98750.08110.046*
C14−0.2546 (3)1.08165 (11)0.10638 (8)0.0402 (4)
H14A−0.16741.09120.15350.048*
H14B−0.18561.12730.07520.048*
C15−0.4906 (3)0.85897 (10)0.08751 (8)0.0392 (4)
H15A−0.60070.89550.05380.047*
H15B−0.61070.83890.12360.047*
C16−0.3880 (4)0.77747 (11)0.04926 (8)0.0465 (4)
H16A−0.30100.73660.08400.056*
H16B−0.54520.74650.02620.056*
N10.4640 (3)1.06489 (9)0.25999 (7)0.0415 (3)
N20.0550 (2)0.94980 (8)0.20978 (6)0.0333 (3)
N3−0.2733 (3)0.91507 (8)0.12111 (6)0.0374 (3)
O1−0.5458 (2)1.09241 (8)0.10935 (6)0.0499 (3)
H4−0.58261.07600.14990.075*
O2−0.1971 (3)0.79774 (9)−0.00230 (6)0.0586 (4)
H5−0.28380.8313−0.03770.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0325 (8)0.0333 (8)0.0345 (7)0.0036 (6)0.0044 (6)−0.0001 (6)
C20.0433 (9)0.0355 (8)0.0436 (8)−0.0043 (7)0.0027 (7)0.0017 (7)
C30.0524 (10)0.0343 (9)0.0457 (9)0.0012 (7)0.0090 (8)0.0101 (7)
C40.0435 (9)0.0375 (8)0.0366 (8)0.0056 (7)0.0032 (7)0.0059 (6)
C50.0338 (8)0.0350 (8)0.0322 (7)0.0063 (6)0.0043 (6)0.0014 (6)
C60.0331 (9)0.0370 (8)0.0369 (8)0.0080 (6)0.0041 (6)−0.0032 (6)
C70.0436 (10)0.0529 (10)0.0407 (8)0.0079 (8)−0.0035 (7)−0.0069 (7)
C80.0682 (13)0.0704 (13)0.0385 (9)0.0051 (10)−0.0131 (8)0.0081 (8)
C90.0676 (13)0.0566 (11)0.0411 (9)0.0044 (9)−0.0018 (8)0.0161 (8)
C100.0505 (11)0.0736 (14)0.0522 (10)0.0062 (10)−0.0103 (8)−0.0156 (9)
C110.0466 (11)0.0627 (12)0.0694 (12)−0.0077 (9)−0.0009 (9)−0.0228 (10)
C120.0458 (10)0.0443 (10)0.0589 (10)−0.0045 (8)0.0096 (8)−0.0127 (8)
C130.0360 (9)0.0494 (9)0.0306 (7)−0.0033 (7)0.0005 (6)0.0062 (6)
C140.0358 (9)0.0421 (9)0.0423 (8)−0.0042 (7)−0.0003 (7)0.0088 (6)
C150.0342 (9)0.0430 (9)0.0398 (8)0.0002 (7)−0.0022 (6)0.0012 (6)
C160.0522 (11)0.0417 (9)0.0448 (9)0.0025 (7)−0.0047 (8)−0.0014 (7)
N10.0383 (8)0.0410 (7)0.0455 (7)−0.0010 (6)0.0062 (6)−0.0048 (6)
N20.0330 (7)0.0344 (7)0.0327 (6)0.0026 (5)0.0039 (5)0.0027 (5)
N30.0404 (7)0.0374 (7)0.0337 (6)−0.0034 (6)−0.0025 (5)0.0031 (5)
O10.0394 (7)0.0602 (8)0.0502 (7)0.0085 (5)0.0040 (5)0.0163 (5)
O20.0552 (8)0.0697 (9)0.0514 (7)0.0186 (6)0.0069 (6)−0.0034 (6)
Geometric parameters (Å, °) top
C1—N21.3319 (19)C11—C121.386 (3)
C1—N31.3603 (18)C11—H110.9300
C1—C21.427 (2)C12—N11.320 (2)
C2—C31.351 (2)C12—H120.9300
C2—H20.9300C13—N31.4590 (18)
C3—C41.406 (2)C13—C141.501 (2)
C3—H30.9300C13—H13A0.9700
C4—C51.410 (2)C13—H13B0.9700
C4—C91.425 (2)C14—O11.4255 (19)
C5—N21.3539 (18)C14—H14A0.9700
C5—C61.447 (2)C14—H14B0.9700
C6—N11.3573 (19)C15—N31.4574 (19)
C6—C71.415 (2)C15—C161.509 (2)
C7—C101.400 (3)C15—H15A0.9700
C7—C81.427 (3)C15—H15B0.9700
C8—C91.340 (3)C16—O21.415 (2)
C8—H80.9300C16—H16A0.9700
C9—H90.9300C16—H16B0.9700
C10—C111.361 (3)O1—H40.8330
C10—H100.9300O2—H50.9147
N2—C1—N3116.99 (13)N1—C12—H12117.9
N2—C1—C2121.66 (13)C11—C12—H12117.9
N3—C1—C2121.35 (14)N3—C13—C14114.71 (12)
C3—C2—C1119.07 (14)N3—C13—H13A108.6
C3—C2—H2120.5C14—C13—H13A108.6
C1—C2—H2120.5N3—C13—H13B108.6
C2—C3—C4120.81 (14)C14—C13—H13B108.6
C2—C3—H3119.6H13A—C13—H13B107.6
C4—C3—H3119.6O1—C14—C13113.19 (13)
C3—C4—C5116.60 (14)O1—C14—H14A108.9
C3—C4—C9123.31 (15)C13—C14—H14A108.9
C5—C4—C9120.08 (15)O1—C14—H14B108.9
N2—C5—C4123.15 (14)C13—C14—H14B108.9
N2—C5—C6118.39 (13)H14A—C14—H14B107.8
C4—C5—C6118.45 (13)N3—C15—C16114.57 (13)
N1—C6—C7121.82 (14)N3—C15—H15A108.6
N1—C6—C5118.68 (13)C16—C15—H15A108.6
C7—C6—C5119.50 (14)N3—C15—H15B108.6
C10—C7—C6117.59 (16)C16—C15—H15B108.6
C10—C7—C8122.76 (16)H15A—C15—H15B107.6
C6—C7—C8119.65 (15)O2—C16—C15113.97 (13)
C9—C8—C7120.76 (15)O2—C16—H16A108.8
C9—C8—H8119.6C15—C16—H16A108.8
C7—C8—H8119.6O2—C16—H16B108.8
C8—C9—C4121.54 (16)C15—C16—H16B108.8
C8—C9—H9119.2H16A—C16—H16B107.7
C4—C9—H9119.2C12—N1—C6117.92 (14)
C11—C10—C7119.93 (17)C1—N2—C5118.67 (12)
C11—C10—H10120.0C1—N3—C15122.52 (12)
C7—C10—H10120.0C1—N3—C13119.64 (12)
C10—C11—C12118.52 (17)C15—N3—C13117.64 (11)
C10—C11—H11120.7C14—O1—H4105.8
C12—C11—H11120.7C16—O2—H5109.1
N1—C12—C11124.22 (18)
N2—C1—C2—C32.5 (2)C6—C7—C10—C110.1 (3)
N3—C1—C2—C3−177.39 (14)C8—C7—C10—C11179.74 (17)
C1—C2—C3—C4−1.0 (2)C7—C10—C11—C12−0.3 (3)
C2—C3—C4—C5−0.4 (2)C10—C11—C12—N10.2 (3)
C2—C3—C4—C9178.88 (15)N3—C13—C14—O1−56.55 (17)
C3—C4—C5—N20.5 (2)N3—C15—C16—O2−54.91 (18)
C9—C4—C5—N2−178.84 (14)C11—C12—N1—C60.2 (2)
C3—C4—C5—C6179.25 (13)C7—C6—N1—C12−0.4 (2)
C9—C4—C5—C6−0.1 (2)C5—C6—N1—C12179.63 (13)
N2—C5—C6—N1−1.15 (19)N3—C1—N2—C5177.46 (12)
C4—C5—C6—N1−179.99 (13)C2—C1—N2—C5−2.4 (2)
N2—C5—C6—C7178.92 (13)C4—C5—N2—C11.0 (2)
C4—C5—C6—C70.1 (2)C6—C5—N2—C1−177.83 (12)
N1—C6—C7—C100.3 (2)N2—C1—N3—C15177.43 (12)
C5—C6—C7—C10−179.75 (14)C2—C1—N3—C15−2.7 (2)
N1—C6—C7—C8−179.37 (14)N2—C1—N3—C132.72 (19)
C5—C6—C7—C80.5 (2)C2—C1—N3—C13−177.39 (13)
C10—C7—C8—C9179.05 (18)C16—C15—N3—C1−81.85 (17)
C6—C7—C8—C9−1.3 (3)C16—C15—N3—C1392.96 (16)
C7—C8—C9—C41.3 (3)C14—C13—N3—C1−75.61 (17)
C3—C4—C9—C8−179.92 (17)C14—C13—N3—C15109.43 (15)
C5—C4—C9—C8−0.7 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H5···O1i0.911.912.8254 (17)177
O1—H4···N1ii0.832.082.8676 (18)158
Symmetry codes: (i) −x−1, −y+2, −z; (ii) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H5···O1i0.911.912.8254 (17)177
O1—H4···N1ii0.832.082.8676 (18)158
Symmetry codes: (i) −x−1, −y+2, −z; (ii) x−1, y, z.
references
References top

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Li, H., Hu, T. Q. & Zhang, S. G. (2008). Acta Cryst. E64, m771.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Zhang, S. G., Hu, T. Q. & Li, H. (2008). Acta Cryst. E64, m769.