1-(1H-Imidazo[4,5-f][1,10]phenan­throlin-2-yl)naphthalen-2-ol

Wang, X.-Y.; Ma, S.; He, Y.

doi:10.1107/S1600536811005861

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o725

doi:10.1107/S1600536811005861

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1-(1H-Imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol

Xiu-Yan Wang,^a ^* Shuai Ma ^a and Yu He ^a

^aCollege of Chemistry, Jilin Normal University, Siping 136000, People's Republic of China, and Key Laboratory of Preparation and Applications of Environmentally Friendly Materials (Jilin Normal University), Ministry of Education, People's Republic of China
^*Correspondence e-mail: wangxiuyan2001@yahoo.com.cn

(Received 8 February 2011; accepted 16 February 2011; online 26 February 2011)

In the title molecule, C₂₃H₁₄N₄O, the dihedral angle between the pyridine rings of the phenanthroline unit is 4.43 (8)° and the dihedral angle formed by the nine essentially planar [maximum deviation 0.0389 (16)Å] non-H atoms of the benzimidazole unit and the naphthalene ring system is 74.22 (5)°. In the crystal, molecules are linked by intermolecular N—H⋯N and O—H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For background to the coordination chemistry of 1,10-phenanthroline derivatives, see: Wang et al. (2010 ). For the synthetic procedure, see: Steck & Day (1943 ).

Experimental

Crystal data

C₂₃H₁₄N₄O
M_r = 362.38
Tetragonal, I 4₁ c d
a = 22.5800 (4) Å
c = 13.7196 (5) Å
V = 6995.0 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.21 × 0.18 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.41, T_max = 0.72
18374 measured reflections
3433 independent reflections
3153 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.081
S = 1.06
3433 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 1629 Friedel pairs
Flack parameter: 0.0 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N2ⁱ	0.86	2.17	2.9361 (19)	149
N4—H4⋯N1ⁱ	0.86	2.50	3.191 (2)	138
O1—H1⋯N3ⁱⁱ	0.82	2.01	2.7203 (17)	145
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[y, -x+{\script{1\over 2}}, z+{\script{1\over 4}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005861/lh5209sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005861/lh5209Isup2.hkl

checkCIF report

Comment top

1,10-Phenanthroline and its derivatives, are potentially important chelating ligands with excellent coordinating abilities and have been extensively used to build supramolecular architectures (Wang et al., 2010). We report herein the synthesis and crystal structure of the title compound

The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the pyridine rings of the phenanthroline unit [N2/C4-C8 and N1/C1/C2/C3/C11/C23] is 4.43 (8)Å and the dihedral angle formed by the nine essentially planar non-hydrogen atoms of the benzimidazole unit [C3/C4/C8-C12; maximum deviation 0.0389 (16)Å for C4] and the naphthalene ring system is 74.22 (5)°. In the crystal, molecules are linked by intermolecular N—H···N and O—H···N hydrogen bonds to form a three-dimensional network.

Related literature top

For background to the coordination chemistry of 1,10-phenanthroline derivatives, see: Wang et al. (2010). For the synthetic procedure, see: Steck & Day (1943).

Experimental top

The title compound was synthesized according to the literature method of Steck & Day (1943). We carried out the following reaction but the unreacted title compound was found in the reaction vessel. A mixture of Bi(NO₃)₃^.5H₂O (0.5 mmol) and L (0.5 mmol) in 10 mL distilled water was heated at 463 K in a Teflon-lined stainless steel autoclave for three days. The reaction system was then slowly cooled to room temperature. Pale yellow crystals suitable for single crystal X-ray diffraction analysis were collected from the final reaction system.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of of the title compound showing displacement ellipsoids drawn at the 30% probability.

1-(1H-Imidazo[4,5-f][1,10]phenanthrolin-2-yl)naphthalen-2-ol top

Crystal data top

C₂₃H₁₄N₄O	D_x = 1.376 Mg m⁻³
M_r = 362.38	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁cd	Cell parameters from 3433 reflections
Hall symbol: I 4bw -2c	θ = 1.8–26.0°
a = 22.5800 (4) Å	µ = 0.09 mm⁻¹
c = 13.7196 (5) Å	T = 293 K
V = 6995.0 (3) Å³	Block, pale yellow
Z = 16	0.30 × 0.21 × 0.18 mm
F(000) = 3008

Data collection top

Bruker APEX diffractometer	3433 independent reflections
Radiation source: fine-focus sealed tube	3153 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −27→27
T_min = 0.41, T_max = 0.72	k = −27→20
18374 measured reflections	l = −16→16

Refinement top

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)] = 0.031	H-atom parameters constrained
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0457P)² + 1.1603P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3433 reflections	Δρ_max = 0.12 e Å⁻³
253 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1629 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (13)

Crystal data top

C₂₃H₁₄N₄O	Z = 16
M_r = 362.38	Mo Kα radiation
Tetragonal, I4₁cd	µ = 0.09 mm⁻¹
a = 22.5800 (4) Å	T = 293 K
c = 13.7196 (5) Å	0.30 × 0.21 × 0.18 mm
V = 6995.0 (3) Å³

Data collection top

Bruker APEX diffractometer	3433 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3153 reflections with I > 2σ(I)
T_min = 0.41, T_max = 0.72	R_int = 0.022
18374 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.081	Δρ_max = 0.12 e Å⁻³
S = 1.06	Δρ_min = −0.14 e Å⁻³
3433 reflections	Absolute structure: Flack (1983), 1629 Friedel pairs
253 parameters	Absolute structure parameter: 0.0 (13)
1 restraint

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N4	0.15231 (6)	0.04557 (6)	0.26423 (9)	0.0422 (3)
H4	0.1345	0.0224	0.3045	0.051*
O1	0.15580 (7)	0.17926 (6)	0.40232 (9)	0.0690 (4)
H1	0.1466	0.2049	0.4418	0.104*
N1	0.14620 (7)	0.08057 (7)	−0.13144 (9)	0.0534 (4)
C14	0.19348 (7)	0.14069 (7)	0.44439 (12)	0.0468 (4)
N2	0.08332 (6)	−0.01202 (7)	−0.06297 (11)	0.0569 (4)
C4	0.11269 (7)	0.02173 (7)	0.00293 (11)	0.0442 (4)
C12	0.19309 (6)	0.08738 (6)	0.28685 (10)	0.0389 (3)
N3	0.21230 (5)	0.11616 (5)	0.20892 (9)	0.0398 (3)
C11	0.18392 (7)	0.10501 (6)	0.02914 (10)	0.0386 (3)
C3	0.14849 (6)	0.07058 (7)	−0.03403 (10)	0.0421 (3)
C18	0.25212 (6)	0.05078 (7)	0.42951 (11)	0.0437 (3)
C13	0.21381 (7)	0.09461 (7)	0.38867 (11)	0.0410 (3)
C20	0.31013 (8)	−0.03905 (8)	0.41619 (17)	0.0641 (5)
H20	0.3238	−0.0707	0.3791	0.077*
C9	0.14476 (6)	0.04705 (6)	0.16521 (10)	0.0390 (3)
C1	0.21610 (9)	0.15939 (8)	−0.11023 (13)	0.0585 (5)
H1A	0.2389	0.1889	−0.1391	0.070*
C19	0.27385 (7)	0.00224 (8)	0.37510 (13)	0.0516 (4)
H19	0.2632	−0.0016	0.3099	0.062*
C21	0.30698 (8)	0.01212 (10)	0.56875 (15)	0.0677 (6)
H21	0.3185	0.0151	0.6337	0.081*
C15	0.21017 (8)	0.14513 (9)	0.54344 (13)	0.0576 (4)
H15	0.1961	0.1762	0.5815	0.069*
C8	0.10968 (7)	0.01000 (7)	0.10380 (11)	0.0422 (3)
C10	0.18153 (6)	0.09101 (6)	0.13142 (10)	0.0373 (3)
C7	0.07478 (8)	−0.03699 (8)	0.13643 (14)	0.0582 (4)
H7	0.0721	−0.0458	0.2025	0.070*
C17	0.26900 (7)	0.05588 (8)	0.52860 (13)	0.0516 (4)
C2	0.17893 (9)	0.12442 (9)	−0.16609 (13)	0.0613 (5)
H2	0.1768	0.1323	−0.2325	0.074*
C16	0.24695 (8)	0.10373 (10)	0.58300 (13)	0.0601 (5)
H16	0.2578	0.1073	0.6481	0.072*
C5	0.05054 (10)	−0.05570 (10)	−0.02947 (17)	0.0720 (6)
H5	0.0300	−0.0787	−0.0744	0.086*
C6	0.04461 (9)	−0.06976 (9)	0.06877 (17)	0.0729 (6)
H6	0.0205	−0.1010	0.0882	0.087*
C23	0.21879 (8)	0.14991 (7)	−0.01156 (12)	0.0473 (4)
H23	0.2433	0.1729	0.0276	0.057*
C22	0.32682 (9)	−0.03397 (10)	0.51413 (19)	0.0726 (6)
H22	0.3516	−0.0623	0.5419	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N4	0.0482 (7)	0.0475 (7)	0.0308 (6)	−0.0029 (6)	0.0025 (5)	0.0074 (5)
O1	0.0956 (10)	0.0655 (8)	0.0461 (7)	0.0325 (7)	−0.0183 (7)	−0.0127 (6)
N1	0.0634 (9)	0.0683 (9)	0.0286 (6)	0.0102 (7)	0.0019 (6)	−0.0026 (6)
C14	0.0506 (8)	0.0539 (9)	0.0358 (8)	0.0075 (7)	−0.0057 (7)	0.0015 (7)
N2	0.0590 (8)	0.0651 (9)	0.0467 (8)	−0.0034 (7)	0.0024 (7)	−0.0196 (7)
C4	0.0427 (8)	0.0511 (9)	0.0387 (8)	0.0058 (7)	0.0031 (6)	−0.0095 (7)
C12	0.0418 (7)	0.0431 (7)	0.0318 (7)	0.0050 (6)	−0.0003 (6)	0.0024 (6)
N3	0.0430 (6)	0.0443 (6)	0.0321 (6)	0.0014 (5)	0.0008 (5)	0.0029 (5)
C11	0.0424 (7)	0.0433 (8)	0.0303 (7)	0.0072 (6)	0.0043 (6)	0.0024 (6)
C3	0.0438 (8)	0.0503 (8)	0.0321 (8)	0.0092 (6)	0.0043 (6)	−0.0041 (6)
C18	0.0381 (7)	0.0521 (8)	0.0409 (8)	−0.0018 (6)	−0.0005 (6)	0.0117 (7)
C13	0.0442 (8)	0.0489 (8)	0.0299 (7)	0.0002 (6)	−0.0014 (6)	0.0058 (6)
C20	0.0497 (9)	0.0542 (10)	0.0883 (15)	0.0043 (7)	0.0029 (10)	0.0120 (10)
C9	0.0421 (7)	0.0444 (8)	0.0304 (7)	0.0022 (6)	0.0033 (6)	0.0036 (6)
C1	0.0691 (11)	0.0645 (11)	0.0417 (9)	0.0023 (8)	0.0123 (8)	0.0152 (8)
C19	0.0458 (8)	0.0523 (9)	0.0566 (10)	0.0011 (7)	0.0016 (7)	0.0069 (8)
C21	0.0561 (10)	0.0880 (15)	0.0590 (11)	−0.0003 (10)	−0.0157 (9)	0.0290 (10)
C15	0.0649 (10)	0.0704 (11)	0.0375 (9)	0.0043 (8)	−0.0026 (8)	−0.0084 (8)
C8	0.0417 (8)	0.0443 (8)	0.0405 (8)	0.0017 (6)	0.0039 (6)	−0.0036 (6)
C10	0.0398 (7)	0.0424 (8)	0.0297 (7)	0.0029 (6)	0.0016 (6)	0.0008 (6)
C7	0.0633 (11)	0.0557 (10)	0.0557 (11)	−0.0100 (8)	0.0084 (8)	0.0002 (8)
C17	0.0441 (8)	0.0673 (10)	0.0433 (9)	−0.0035 (7)	−0.0061 (7)	0.0154 (8)
C2	0.0767 (12)	0.0770 (12)	0.0302 (8)	0.0113 (10)	0.0063 (8)	0.0087 (8)
C16	0.0627 (10)	0.0864 (13)	0.0314 (7)	−0.0018 (10)	−0.0115 (8)	0.0070 (8)
C5	0.0764 (13)	0.0718 (12)	0.0679 (13)	−0.0183 (10)	0.0033 (11)	−0.0268 (11)
C6	0.0809 (13)	0.0620 (12)	0.0756 (15)	−0.0267 (10)	0.0108 (11)	−0.0115 (10)
C23	0.0529 (9)	0.0505 (9)	0.0387 (8)	0.0023 (7)	0.0061 (7)	0.0043 (7)
C22	0.0569 (11)	0.0678 (13)	0.0932 (16)	0.0089 (9)	−0.0099 (11)	0.0312 (12)

Geometric parameters (Å, º) top

N4—C12	1.3548 (19)	C20—H20	0.9300
N4—C9	1.3697 (19)	C9—C10	1.375 (2)
N4—H4	0.8600	C9—C8	1.427 (2)
O1—C14	1.3476 (18)	C1—C23	1.372 (2)
O1—H1	0.8200	C1—C2	1.384 (3)
N1—C2	1.324 (2)	C1—H1A	0.9300
N1—C3	1.3563 (19)	C19—H19	0.9300
C14—C13	1.370 (2)	C21—C22	1.358 (3)
C14—C15	1.414 (2)	C21—C17	1.420 (2)
N2—C5	1.316 (3)	C21—H21	0.9300
N2—C4	1.356 (2)	C15—C16	1.363 (3)
C4—C8	1.411 (2)	C15—H15	0.9300
C4—C3	1.459 (2)	C8—C7	1.395 (2)
C12—N3	1.3241 (18)	C7—C6	1.369 (3)
C12—C13	1.482 (2)	C7—H7	0.9300
N3—C10	1.3912 (19)	C17—C16	1.404 (3)
C11—C23	1.400 (2)	C2—H2	0.9300
C11—C3	1.413 (2)	C16—H16	0.9300
C11—C10	1.4394 (19)	C5—C6	1.391 (3)
C18—C19	1.414 (2)	C5—H5	0.9300
C18—C17	1.417 (2)	C6—H6	0.9300
C18—C13	1.429 (2)	C23—H23	0.9300
C20—C19	1.363 (3)	C22—H22	0.9300
C20—C22	1.400 (3)

C12—N4—C9	107.15 (12)	C20—C19—H19	119.3
C12—N4—H4	126.4	C18—C19—H19	119.3
C9—N4—H4	126.4	C22—C21—C17	121.23 (19)
C14—O1—H1	109.5	C22—C21—H21	119.4
C2—N1—C3	117.19 (16)	C17—C21—H21	119.4
O1—C14—C13	117.60 (14)	C16—C15—C14	119.76 (17)
O1—C14—C15	122.28 (14)	C16—C15—H15	120.1
C13—C14—C15	120.07 (14)	C14—C15—H15	120.1
C5—N2—C4	117.62 (16)	C7—C8—C4	118.98 (16)
N2—C4—C8	121.68 (15)	C7—C8—C9	124.73 (15)
N2—C4—C3	117.67 (14)	C4—C8—C9	116.26 (14)
C8—C4—C3	120.64 (14)	C9—C10—N3	109.79 (12)
N3—C12—N4	112.31 (13)	C9—C10—C11	120.66 (13)
N3—C12—C13	127.13 (13)	N3—C10—C11	129.55 (13)
N4—C12—C13	120.47 (13)	C6—C7—C8	118.34 (18)
C12—N3—C10	104.67 (11)	C6—C7—H7	120.8
C23—C11—C3	118.18 (14)	C8—C7—H7	120.8
C23—C11—C10	124.68 (14)	C16—C17—C18	118.50 (15)
C3—C11—C10	117.14 (13)	C16—C17—C21	122.93 (18)
N1—C3—C11	122.32 (15)	C18—C17—C21	118.57 (18)
N1—C3—C4	116.56 (14)	N1—C2—C1	124.50 (16)
C11—C3—C4	121.11 (13)	N1—C2—H2	117.8
C19—C18—C17	118.45 (15)	C1—C2—H2	117.8
C19—C18—C13	122.67 (14)	C15—C16—C17	122.14 (16)
C17—C18—C13	118.88 (15)	C15—C16—H16	118.9
C14—C13—C18	120.65 (14)	C17—C16—H16	118.9
C14—C13—C12	120.25 (13)	N2—C5—C6	124.30 (18)
C18—C13—C12	118.97 (14)	N2—C5—H5	117.9
C19—C20—C22	120.18 (19)	C6—C5—H5	117.9
C19—C20—H20	119.9	C7—C6—C5	119.06 (18)
C22—C20—H20	119.9	C7—C6—H6	120.5
N4—C9—C10	106.07 (13)	C5—C6—H6	120.5
N4—C9—C8	129.82 (13)	C1—C23—C11	118.80 (17)
C10—C9—C8	124.02 (13)	C1—C23—H23	120.6
C23—C1—C2	118.97 (17)	C11—C23—H23	120.6
C23—C1—H1A	120.5	C21—C22—C20	120.22 (17)
C2—C1—H1A	120.5	C21—C22—H22	119.9
C20—C19—C18	121.35 (17)	C20—C22—H22	119.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2ⁱ	0.86	2.17	2.9361 (19)	149
N4—H4···N1ⁱ	0.86	2.50	3.191 (2)	138
O1—H1···N3ⁱⁱ	0.82	2.01	2.7203 (17)	145

Symmetry codes: (i) x, −y, z+1/2; (ii) y, −x+1/2, z+1/4.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₄N₄O
M_r	362.38
Crystal system, space group	Tetragonal, I4₁cd
Temperature (K)	293
a, c (Å)	22.5800 (4), 13.7196 (5)
V (Å³)	6995.0 (3)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.21 × 0.18

Data collection
Diffractometer	Bruker APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.41, 0.72
No. of measured, independent and observed [I > 2σ(I)] reflections	18374, 3433, 3153
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.081, 1.06
No. of reflections	3433
No. of parameters	253
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.14
Absolute structure	Flack (1983), 1629 Friedel pairs
Absolute structure parameter	0.0 (13)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), 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
N4—H4···N2ⁱ	0.86	2.17	2.9361 (19)	149
N4—H4···N1ⁱ	0.86	2.50	3.191 (2)	138
O1—H1···N3ⁱⁱ	0.82	2.01	2.7203 (17)	145

Symmetry codes: (i) x, −y, z+1/2; (ii) y, −x+1/2, z+1/4.

Acknowledgements

The authors thank the Key Laboratory of Preparation and Applications of Environmentally Friendly Materials and the Institute Foundation of Siping City (No. 2009011) for supporting this work.

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