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

Jin, X.; Li, J.M.

doi:10.1107/S1600536809004929

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o541

doi:10.1107/S1600536809004929

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

Xia Jin ^a and Jin Min Li ^a ^*

^aChemistry and Chemical Engineering College, Shanxi Datong University, Datong 037009, People's Republic of China
^*Correspondence e-mail: jinminli1957@yahoo.com.cn

(Received 3 February 2009; accepted 11 February 2009; online 18 February 2009)

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 π–π stacking interactions with a centroid–centroid distance of 3.5494 (12) Å.

Related literature

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

Crystal data

C₁₆H₁₇N₃O₂
M_r = 283.33
Monoclinic, P 2₁ /c
a = 4.8480 (10) Å
b = 14.854 (3) Å
c = 18.858 (4) Å
β = 93.523 (3)°
V = 1355.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.54 × 0.32 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.951, T_max = 0.982
7520 measured reflections
2765 independent reflections
2149 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.132
S = 1.03
2765 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H5⋯O1ⁱ	0.91	1.91	2.8254 (17)	177
O1—H4⋯N1ⁱⁱ	0.83	2.08	2.8676 (18)	158
Symmetry codes: (i) -x-1, -y+2, -z; (ii) x-1, y, z.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004929/lh2772sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004929/lh2772Isup2.hkl

checkCIF report

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···Cg2ⁱⁱⁱ_perp = 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···Cg2ⁱⁱⁱ_perp 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.

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

	Fig. 1. The molecular structure of (I), showing the the atom numbering scheme with thermal ellipsoids drawn at the 30% probability level
	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

C₁₆H₁₇N₃O₂	F(000) = 600
M_r = 283.33	D_x = 1.388 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2381 reflections
a = 4.848 (1) Å	θ = 2.6–27.3°
b = 14.854 (3) Å	µ = 0.09 mm⁻¹
c = 18.858 (4) Å	T = 298 K
β = 93.523 (3)°	Block, yellow
V = 1355.5 (5) Å³	0.54 × 0.32 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2765 independent reflections
Radiation source: fine-focus sealed tube	2149 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 26.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→6
T_min = 0.951, T_max = 0.982	k = −12→18
7520 measured reflections	l = −23→23

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0762P)² + 0.108P] where P = (F_o² + 2F_c²)/3
2765 reflections	(Δ/σ)_max = 0.008
190 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₆H₁₇N₃O₂	V = 1355.5 (5) Å³
M_r = 283.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.848 (1) Å	µ = 0.09 mm⁻¹
b = 14.854 (3) Å	T = 298 K
c = 18.858 (4) Å	0.54 × 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)
T_min = 0.951, T_max = 0.982	R_int = 0.030
7520 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
2765 reflections	Δρ_min = −0.16 e Å⁻³
190 parameters

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

	x	y	z	U_iso*/U_eq
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	−0.3697	0.7814	0.2077	0.049*
C3	−0.1090 (4)	0.80542 (11)	0.29126 (8)	0.0439 (4)
H3	−0.1645	0.7569	0.3181	0.053*
C4	0.1020 (3)	0.86265 (10)	0.31895 (8)	0.0391 (4)
C5	0.1770 (3)	0.93444 (10)	0.27517 (7)	0.0336 (3)
C6	0.3910 (3)	0.99566 (10)	0.30193 (7)	0.0356 (4)
C7	0.5185 (3)	0.98199 (12)	0.37060 (8)	0.0460 (4)
C8	0.4363 (4)	0.90765 (14)	0.41232 (9)	0.0597 (5)
H8	0.5227	0.8980	0.4571	0.072*
C9	0.2361 (4)	0.85156 (13)	0.38776 (9)	0.0553 (5)
H9	0.1833	0.8043	0.4163	0.066*
C10	0.7237 (4)	1.04302 (14)	0.39446 (10)	0.0593 (5)
H10	0.8122	1.0362	0.4393	0.071*
C11	0.7935 (4)	1.11242 (14)	0.35196 (11)	0.0598 (5)
H11	0.9289	1.1536	0.3673	0.072*
C12	0.6584 (4)	1.12040 (12)	0.28535 (10)	0.0494 (4)
H12	0.7079	1.1679	0.2567	0.059*
C13	−0.1736 (3)	0.99054 (11)	0.08028 (7)	0.0387 (4)
H13A	−0.2437	0.9841	0.0313	0.046*
H13B	0.0264	0.9875	0.0811	0.046*
C14	−0.2546 (3)	1.08165 (11)	0.10638 (8)	0.0402 (4)
H14A	−0.1674	1.0912	0.1535	0.048*
H14B	−0.1856	1.1273	0.0752	0.048*
C15	−0.4906 (3)	0.85897 (10)	0.08751 (8)	0.0392 (4)
H15A	−0.6007	0.8955	0.0538	0.047*
H15B	−0.6107	0.8389	0.1236	0.047*
C16	−0.3880 (4)	0.77747 (11)	0.04926 (8)	0.0465 (4)
H16A	−0.3010	0.7366	0.0840	0.056*
H16B	−0.5452	0.7465	0.0262	0.056*
N1	0.4640 (3)	1.06489 (9)	0.25999 (7)	0.0415 (3)
N2	0.0550 (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	−0.5826	1.0760	0.1499	0.075*
O2	−0.1971 (3)	0.79774 (9)	−0.00230 (6)	0.0586 (4)
H5	−0.2838	0.8313	−0.0377	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0325 (8)	0.0333 (8)	0.0345 (7)	0.0036 (6)	0.0044 (6)	−0.0001 (6)
C2	0.0433 (9)	0.0355 (8)	0.0436 (8)	−0.0043 (7)	0.0027 (7)	0.0017 (7)
C3	0.0524 (10)	0.0343 (9)	0.0457 (9)	0.0012 (7)	0.0090 (8)	0.0101 (7)
C4	0.0435 (9)	0.0375 (8)	0.0366 (8)	0.0056 (7)	0.0032 (7)	0.0059 (6)
C5	0.0338 (8)	0.0350 (8)	0.0322 (7)	0.0063 (6)	0.0043 (6)	0.0014 (6)
C6	0.0331 (9)	0.0370 (8)	0.0369 (8)	0.0080 (6)	0.0041 (6)	−0.0032 (6)
C7	0.0436 (10)	0.0529 (10)	0.0407 (8)	0.0079 (8)	−0.0035 (7)	−0.0069 (7)
C8	0.0682 (13)	0.0704 (13)	0.0385 (9)	0.0051 (10)	−0.0131 (8)	0.0081 (8)
C9	0.0676 (13)	0.0566 (11)	0.0411 (9)	0.0044 (9)	−0.0018 (8)	0.0161 (8)
C10	0.0505 (11)	0.0736 (14)	0.0522 (10)	0.0062 (10)	−0.0103 (8)	−0.0156 (9)
C11	0.0466 (11)	0.0627 (12)	0.0694 (12)	−0.0077 (9)	−0.0009 (9)	−0.0228 (10)
C12	0.0458 (10)	0.0443 (10)	0.0589 (10)	−0.0045 (8)	0.0096 (8)	−0.0127 (8)
C13	0.0360 (9)	0.0494 (9)	0.0306 (7)	−0.0033 (7)	0.0005 (6)	0.0062 (6)
C14	0.0358 (9)	0.0421 (9)	0.0423 (8)	−0.0042 (7)	−0.0003 (7)	0.0088 (6)
C15	0.0342 (9)	0.0430 (9)	0.0398 (8)	0.0002 (7)	−0.0022 (6)	0.0012 (6)
C16	0.0522 (11)	0.0417 (9)	0.0448 (9)	0.0025 (7)	−0.0047 (8)	−0.0014 (7)
N1	0.0383 (8)	0.0410 (7)	0.0455 (7)	−0.0010 (6)	0.0062 (6)	−0.0048 (6)
N2	0.0330 (7)	0.0344 (7)	0.0327 (6)	0.0026 (5)	0.0039 (5)	0.0027 (5)
N3	0.0404 (7)	0.0374 (7)	0.0337 (6)	−0.0034 (6)	−0.0025 (5)	0.0031 (5)
O1	0.0394 (7)	0.0602 (8)	0.0502 (7)	0.0085 (5)	0.0040 (5)	0.0163 (5)
O2	0.0552 (8)	0.0697 (9)	0.0514 (7)	0.0186 (6)	0.0069 (6)	−0.0034 (6)

Geometric parameters (Å, º) top

C1—N2	1.3319 (19)	C11—C12	1.386 (3)
C1—N3	1.3603 (18)	C11—H11	0.9300
C1—C2	1.427 (2)	C12—N1	1.320 (2)
C2—C3	1.351 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—N3	1.4590 (18)
C3—C4	1.406 (2)	C13—C14	1.501 (2)
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.410 (2)	C13—H13B	0.9700
C4—C9	1.425 (2)	C14—O1	1.4255 (19)
C5—N2	1.3539 (18)	C14—H14A	0.9700
C5—C6	1.447 (2)	C14—H14B	0.9700
C6—N1	1.3573 (19)	C15—N3	1.4574 (19)
C6—C7	1.415 (2)	C15—C16	1.509 (2)
C7—C10	1.400 (3)	C15—H15A	0.9700
C7—C8	1.427 (3)	C15—H15B	0.9700
C8—C9	1.340 (3)	C16—O2	1.415 (2)
C8—H8	0.9300	C16—H16A	0.9700
C9—H9	0.9300	C16—H16B	0.9700
C10—C11	1.361 (3)	O1—H4	0.8330
C10—H10	0.9300	O2—H5	0.9147

N2—C1—N3	116.99 (13)	N1—C12—H12	117.9
N2—C1—C2	121.66 (13)	C11—C12—H12	117.9
N3—C1—C2	121.35 (14)	N3—C13—C14	114.71 (12)
C3—C2—C1	119.07 (14)	N3—C13—H13A	108.6
C3—C2—H2	120.5	C14—C13—H13A	108.6
C1—C2—H2	120.5	N3—C13—H13B	108.6
C2—C3—C4	120.81 (14)	C14—C13—H13B	108.6
C2—C3—H3	119.6	H13A—C13—H13B	107.6
C4—C3—H3	119.6	O1—C14—C13	113.19 (13)
C3—C4—C5	116.60 (14)	O1—C14—H14A	108.9
C3—C4—C9	123.31 (15)	C13—C14—H14A	108.9
C5—C4—C9	120.08 (15)	O1—C14—H14B	108.9
N2—C5—C4	123.15 (14)	C13—C14—H14B	108.9
N2—C5—C6	118.39 (13)	H14A—C14—H14B	107.8
C4—C5—C6	118.45 (13)	N3—C15—C16	114.57 (13)
N1—C6—C7	121.82 (14)	N3—C15—H15A	108.6
N1—C6—C5	118.68 (13)	C16—C15—H15A	108.6
C7—C6—C5	119.50 (14)	N3—C15—H15B	108.6
C10—C7—C6	117.59 (16)	C16—C15—H15B	108.6
C10—C7—C8	122.76 (16)	H15A—C15—H15B	107.6
C6—C7—C8	119.65 (15)	O2—C16—C15	113.97 (13)
C9—C8—C7	120.76 (15)	O2—C16—H16A	108.8
C9—C8—H8	119.6	C15—C16—H16A	108.8
C7—C8—H8	119.6	O2—C16—H16B	108.8
C8—C9—C4	121.54 (16)	C15—C16—H16B	108.8
C8—C9—H9	119.2	H16A—C16—H16B	107.7
C4—C9—H9	119.2	C12—N1—C6	117.92 (14)
C11—C10—C7	119.93 (17)	C1—N2—C5	118.67 (12)
C11—C10—H10	120.0	C1—N3—C15	122.52 (12)
C7—C10—H10	120.0	C1—N3—C13	119.64 (12)
C10—C11—C12	118.52 (17)	C15—N3—C13	117.64 (11)
C10—C11—H11	120.7	C14—O1—H4	105.8
C12—C11—H11	120.7	C16—O2—H5	109.1
N1—C12—C11	124.22 (18)

N2—C1—C2—C3	2.5 (2)	C6—C7—C10—C11	0.1 (3)
N3—C1—C2—C3	−177.39 (14)	C8—C7—C10—C11	179.74 (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—N1	0.2 (3)
C2—C3—C4—C9	178.88 (15)	N3—C13—C14—O1	−56.55 (17)
C3—C4—C5—N2	0.5 (2)	N3—C15—C16—O2	−54.91 (18)
C9—C4—C5—N2	−178.84 (14)	C11—C12—N1—C6	0.2 (2)
C3—C4—C5—C6	179.25 (13)	C7—C6—N1—C12	−0.4 (2)
C9—C4—C5—C6	−0.1 (2)	C5—C6—N1—C12	179.63 (13)
N2—C5—C6—N1	−1.15 (19)	N3—C1—N2—C5	177.46 (12)
C4—C5—C6—N1	−179.99 (13)	C2—C1—N2—C5	−2.4 (2)
N2—C5—C6—C7	178.92 (13)	C4—C5—N2—C1	1.0 (2)
C4—C5—C6—C7	0.1 (2)	C6—C5—N2—C1	−177.83 (12)
N1—C6—C7—C10	0.3 (2)	N2—C1—N3—C15	177.43 (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—C13	2.72 (19)
C5—C6—C7—C8	0.5 (2)	C2—C1—N3—C13	−177.39 (13)
C10—C7—C8—C9	179.05 (18)	C16—C15—N3—C1	−81.85 (17)
C6—C7—C8—C9	−1.3 (3)	C16—C15—N3—C13	92.96 (16)
C7—C8—C9—C4	1.3 (3)	C14—C13—N3—C1	−75.61 (17)
C3—C4—C9—C8	−179.92 (17)	C14—C13—N3—C15	109.43 (15)
C5—C4—C9—C8	−0.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H5···O1ⁱ	0.91	1.91	2.8254 (17)	177
O1—H4···N1ⁱⁱ	0.83	2.08	2.8676 (18)	158

Symmetry codes: (i) −x−1, −y+2, −z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O₂
M_r	283.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	4.848 (1), 14.854 (3), 18.858 (4)
β (°)	93.523 (3)
V (Å³)	1355.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.54 × 0.32 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.951, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	7520, 2765, 2149
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.132, 1.03
No. of reflections	2765
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.16

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H5···O1ⁱ	0.91	1.91	2.8254 (17)	176.7
O1—H4···N1ⁱⁱ	0.83	2.08	2.8676 (18)	157.5

Symmetry codes: (i) −x−1, −y+2, −z; (ii) x−1, y, z.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, H., Hu, T. Q. & Zhang, S. G. (2008). Acta Cryst. E64, m771. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, S. G., Hu, T. Q. & Li, H. (2008). Acta Cryst. E64, m769. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 3| March 2009| Page o541

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