2-[(E)-(1,10-Phenanthrolin-5-yl)imino-meth-yl]phenol methanol monosolvate.

In the title multi-donor Schiff base compound, C(19)H(13)N(3)O·CH(3)OH, the dihedral angle between the mean planes of the phenanthroline and phenol rings is 59.3 (1)°. The Schiff base mol-ecule is linked to the solvent mol-ecule by an O-H⋯O hydrogen bond. In the crystal, the components are linked by O-H⋯N hydrogen bonds, weak O-H⋯N inter-actions and π-π stacking inter-actions [centroid-centroid distances = 3.701 (1) and 3.656 (1) Å].

Related literature

For the role played by 1,10-phenanthroline and its derivatives as mol­ecular scaffolds for supra­molecular assemblies, see: Balzani et al. (1996 ▶). For the metal-chelating properties of the 1,10-phenanthroline ligand, see: Sammes & Yahioglu (1994 ▶). For the photochemical and redox properties of phenanthroline rings, see: Camren et al. (1996 ▶); Bolger et al. (1996 ▶); Msood & Hodgson (1993 ▶). For Schiff bases as oxygen-carriers and as photochromic or thermochromic materials, see: Hobday & Smith (1973 ▶); Gul et al. (1986 ▶); Can & Bekaroglu (1988 ▶); Avciata et al. (1995 ▶, 1998 ▶); Demirhan et al. (2002 ▶). For the synthesis of 5-amino-1,10-phenanthroline, see: Gillard & Hill (1974 ▶). For related structures, see: Wu et al. (2011 ▶); Fun et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H13N3O·CH4O

M = 331.37

Monoclinic,

a = 11.9398 (12) Å

b = 4.6680 (5) Å

c = 14.7818 (18) Å

β = 101.961 (11)°

V = 805.98 (16) Å3

Z = 2

Cu Kα radiation

μ = 0.73 mm−1

T = 123 K

1.15 × 0.84 × 0.06 mm

Data collection

Oxford Diffraction Gemini-R diffractometer

Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007 ▶), using a multi-faceted crystal model (Clark & Reid, 1995 ▶)] T min = 0.505, T max = 0.954

3176 measured reflections

1960 independent reflections

1885 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.04

1960 reflections

229 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011890/jj2127sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011890/jj2127Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011890/jj2127Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H13N3O·CH4O	F(000) = 348
Mr = 331.37	Dx = 1.365 Mg m−3
Monoclinic, Pc	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P -2yc	Cell parameters from 1347 reflections
a = 11.9398 (12) Å	θ = 3.1–75.2°
b = 4.6680 (5) Å	µ = 0.73 mm−1
c = 14.7818 (18) Å	T = 123 K
β = 101.961 (11)°	Triangular plate, yellow
V = 805.98 (16) Å3	1.15 × 0.84 × 0.06 mm
Z = 2

Oxford Diffraction Gemini-R diffractometer	1960 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1885 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 10.5081 pixels mm-1	θmax = 75.2°, θmin = 3.1°
ω scans	h = −13→14
Absorption correction: analytical [CrysAlis RED (Oxford Diffraction, 2007), using a multi-faceted crystal model (Clark & Reid, 1995)]	k = −5→5
Tmin = 0.505, Tmax = 0.954	l = −18→12
3176 measured reflections

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0747P)2 + 0.0897P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1960 reflections	Δρmax = 0.24 e Å−3
229 parameters	Δρmin = −0.17 e Å−3
2 restraints	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881, 303 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −1.5 (18)

Experimental. The crystal was very fragile. On cutting the crystal shattered so an incident collimator of 1.0 mm was used. IR (KBr): 3435(Ar—OH), 3020(Ar), 1616 (C=N—C). 13 C NMR, 167 (C—OH), 165 (C=C—N), 150,152 and 148 (C=N) p.p.m.. LC—MS, m/z (%): 298 (M-1). In the electronic spectrum two band appears at 281 and 340 nm which can be assigned to the π -π * and n-π * transition of C=C and C=N group.The FTIR spectra were obtained on a Perkin Elmer Spectrum One Bv 5.0 spectrophotometer. 1H NMR and 13C NMR spectra were recorded on a Varian UNITY INOVA 500 MHz s pectrometer. Mass spectra were measured on a FinniganTM LCQTM Advantage MAX spectrometer. Electronic spectra were obtained on a Agilent 8453 UV-Vis. Spectroscopy System. Elemental analyses were obtained on a Thermo Finnigan Flash EA 112. All other chemicals employed were of the highest grade available.Absorption correction: CrysAlis RED, (Oxford Diffraction, 2007) Analytical numeric absorption correction using a multifaceted crystal model (Clark & Reid, 1995).

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.

	x	y	z	Uiso*/Ueq
O1	0.98484 (16)	1.4695 (5)	0.63127 (14)	0.0337 (4)
H1	1.0514	1.5260	0.6545	0.051*
O1S	1.18635 (15)	1.6610 (4)	0.71862 (14)	0.0307 (4)
H1S	1.2497	1.6321	0.7038	0.046*
N1	0.41348 (18)	0.5215 (5)	0.70687 (15)	0.0254 (4)
N2	0.32594 (18)	0.8980 (5)	0.56783 (15)	0.0268 (4)
N3	0.70428 (17)	1.0456 (5)	0.50248 (15)	0.0256 (4)
C1	0.4567 (2)	0.3337 (6)	0.77219 (17)	0.0275 (5)
H1A	0.4061	0.2468	0.8058	0.033*
C2	0.5729 (2)	0.2556 (6)	0.79469 (18)	0.0291 (5)
H2A	0.5997	0.1206	0.8424	0.035*
C3	0.6463 (2)	0.3780 (5)	0.74647 (18)	0.0265 (5)
H3A	0.7252	0.3282	0.7600	0.032*
C4	0.60430 (19)	0.5796 (5)	0.67619 (16)	0.0233 (5)
C5	0.6784 (2)	0.7166 (5)	0.62454 (17)	0.0237 (5)
H5A	0.7577	0.6711	0.6372	0.028*
C6	0.63612 (19)	0.9123 (5)	0.55719 (16)	0.0234 (5)
C7	0.5151 (2)	0.9788 (5)	0.53588 (16)	0.0227 (5)
C8	0.4682 (2)	1.1790 (6)	0.46665 (17)	0.0258 (5)
H8A	0.5159	1.2761	0.4326	0.031*
C9	0.3527 (2)	1.2309 (6)	0.44944 (19)	0.0299 (5)
H9A	0.3191	1.3639	0.4030	0.036*
C10	0.2852 (2)	1.0854 (6)	0.50113 (19)	0.0297 (5)
H10A	0.2052	1.1223	0.4879	0.036*
C11	0.4404 (2)	0.8465 (5)	0.58528 (16)	0.0233 (5)
C12	0.48604 (19)	0.6424 (5)	0.65842 (16)	0.0221 (5)
C13	0.8014 (2)	1.1466 (6)	0.54239 (17)	0.0252 (5)
H13A	0.8229	1.1375	0.6079	0.030*
C14	0.8805 (2)	1.2756 (5)	0.49080 (18)	0.0258 (5)
C15	0.9738 (2)	1.4372 (5)	0.53890 (18)	0.0268 (5)
C16	1.0503 (2)	1.5581 (6)	0.4904 (2)	0.0311 (5)
H16A	1.1138	1.6655	0.5226	0.037*
C17	1.0351 (2)	1.5235 (6)	0.3963 (2)	0.0358 (6)
H17A	1.0878	1.6080	0.3641	0.043*
C18	0.9425 (2)	1.3650 (8)	0.3476 (2)	0.0382 (6)
H18A	0.9323	1.3405	0.2826	0.046*
C19	0.8661 (2)	1.2446 (6)	0.39525 (18)	0.0305 (5)
H19A	0.8027	1.1387	0.3623	0.037*
C1S	1.1695 (2)	1.9603 (6)	0.7274 (2)	0.0368 (6)
H1S1	1.2045	2.0217	0.7903	0.055*
H1S2	1.0873	2.0020	0.7150	0.055*
H1S3	1.2051	2.0636	0.6829	0.055*

	U11	U22	U33	U12	U13	U23
O1	0.0270 (8)	0.0449 (11)	0.0295 (9)	−0.0100 (8)	0.0067 (7)	−0.0060 (8)
O1S	0.0226 (8)	0.0333 (9)	0.0364 (10)	−0.0025 (7)	0.0064 (7)	−0.0027 (8)
N1	0.0220 (9)	0.0255 (10)	0.0282 (10)	−0.0003 (8)	0.0040 (8)	−0.0010 (9)
N2	0.0228 (9)	0.0262 (10)	0.0310 (11)	0.0006 (8)	0.0047 (8)	0.0015 (8)
N3	0.0223 (10)	0.0280 (10)	0.0269 (10)	−0.0002 (8)	0.0061 (8)	−0.0011 (8)
C1	0.0298 (12)	0.0264 (12)	0.0271 (12)	−0.0032 (10)	0.0081 (10)	0.0005 (10)
C2	0.0306 (12)	0.0284 (12)	0.0262 (12)	−0.0009 (10)	0.0011 (9)	0.0011 (9)
C3	0.0243 (11)	0.0253 (11)	0.0277 (12)	0.0021 (9)	0.0002 (9)	−0.0014 (10)
C4	0.0227 (12)	0.0209 (10)	0.0255 (12)	−0.0011 (9)	0.0029 (9)	−0.0024 (9)
C5	0.0203 (10)	0.0243 (11)	0.0260 (11)	0.0004 (9)	0.0035 (8)	−0.0032 (9)
C6	0.0236 (11)	0.0220 (10)	0.0244 (11)	−0.0013 (9)	0.0044 (9)	−0.0041 (9)
C7	0.0227 (10)	0.0212 (10)	0.0233 (11)	−0.0013 (8)	0.0025 (9)	−0.0029 (9)
C8	0.0286 (12)	0.0246 (11)	0.0242 (11)	−0.0008 (9)	0.0053 (9)	−0.0010 (9)
C9	0.0309 (13)	0.0298 (11)	0.0272 (11)	0.0032 (10)	0.0022 (10)	0.0041 (10)
C10	0.0225 (12)	0.0290 (12)	0.0363 (13)	0.0035 (9)	0.0032 (10)	0.0019 (11)
C11	0.0221 (11)	0.0217 (10)	0.0250 (11)	−0.0013 (8)	0.0024 (9)	−0.0033 (9)
C12	0.0206 (10)	0.0206 (11)	0.0246 (11)	−0.0011 (8)	0.0034 (9)	−0.0023 (9)
C13	0.0241 (11)	0.0259 (11)	0.0257 (11)	0.0017 (9)	0.0057 (8)	0.0000 (9)
C14	0.0214 (10)	0.0268 (11)	0.0294 (12)	0.0020 (9)	0.0056 (9)	0.0022 (10)
C15	0.0222 (10)	0.0275 (11)	0.0308 (12)	0.0021 (9)	0.0056 (9)	0.0002 (10)
C16	0.0215 (11)	0.0326 (13)	0.0397 (14)	−0.0031 (10)	0.0072 (10)	0.0021 (11)
C17	0.0248 (11)	0.0432 (14)	0.0417 (15)	0.0030 (11)	0.0123 (10)	0.0150 (12)
C18	0.0313 (13)	0.0560 (18)	0.0273 (12)	0.0040 (12)	0.0061 (10)	0.0063 (12)
C19	0.0228 (11)	0.0403 (14)	0.0279 (12)	−0.0011 (10)	0.0039 (9)	0.0007 (11)
C1S	0.0318 (13)	0.0350 (14)	0.0451 (16)	−0.0016 (11)	0.0115 (11)	−0.0054 (12)

O1—C15	1.353 (3)	C7—C8	1.413 (3)
O1—H1	0.8400	C8—C9	1.371 (4)
O1S—C1S	1.421 (3)	C8—H8A	0.9500
O1S—H1S	0.8400	C9—C10	1.396 (4)
N1—C1	1.327 (3)	C9—H9A	0.9500
N1—C12	1.356 (3)	C10—H10A	0.9500
N2—C10	1.333 (3)	C11—C12	1.459 (3)
N2—C11	1.359 (3)	C13—C14	1.462 (3)
N3—C13	1.277 (3)	C13—H13A	0.9500
N3—C6	1.406 (3)	C14—C19	1.395 (4)
C1—C2	1.406 (4)	C14—C15	1.410 (3)
C1—H1A	0.9500	C15—C16	1.393 (3)
C2—C3	1.365 (4)	C16—C17	1.374 (4)
C2—H2A	0.9500	C16—H16A	0.9500
C3—C4	1.414 (4)	C17—C18	1.399 (4)
C3—H3A	0.9500	C17—H17A	0.9500
C4—C12	1.412 (3)	C18—C19	1.382 (4)
C4—C5	1.434 (3)	C18—H18A	0.9500
C5—C6	1.368 (3)	C19—H19A	0.9500
C5—H5A	0.9500	C1S—H1S1	0.9800
C6—C7	1.447 (3)	C1S—H1S2	0.9800
C7—C11	1.407 (3)	C1S—H1S3	0.9800
C15—O1—H1	109.5	C9—C10—H10A	118.0
C1S—O1S—H1S	109.5	N2—C11—C7	123.0 (2)
C1—N1—C12	117.7 (2)	N2—C11—C12	117.5 (2)
C10—N2—C11	117.1 (2)	C7—C11—C12	119.5 (2)
C13—N3—C6	118.4 (2)	N1—C12—C4	122.6 (2)
N1—C1—C2	124.0 (2)	N1—C12—C11	118.80 (19)
N1—C1—H1A	118.0	C4—C12—C11	118.6 (2)
C2—C1—H1A	118.0	N3—C13—C14	122.3 (2)
C3—C2—C1	118.5 (2)	N3—C13—H13A	118.9
C3—C2—H2A	120.8	C14—C13—H13A	118.9
C1—C2—H2A	120.8	C19—C14—C15	119.0 (2)
C2—C3—C4	119.6 (2)	C19—C14—C13	121.9 (2)
C2—C3—H3A	120.2	C15—C14—C13	119.1 (2)
C4—C3—H3A	120.2	O1—C15—C16	122.5 (2)
C12—C4—C3	117.6 (2)	O1—C15—C14	118.0 (2)
C12—C4—C5	120.8 (2)	C16—C15—C14	119.4 (2)
C3—C4—C5	121.6 (2)	C17—C16—C15	120.7 (2)
C6—C5—C4	120.6 (2)	C17—C16—H16A	119.7
C6—C5—H5A	119.7	C15—C16—H16A	119.7
C4—C5—H5A	119.7	C16—C17—C18	120.5 (3)
C5—C6—N3	122.9 (2)	C16—C17—H17A	119.7
C5—C6—C7	120.2 (2)	C18—C17—H17A	119.7
N3—C6—C7	116.8 (2)	C19—C18—C17	119.2 (3)
C11—C7—C8	117.9 (2)	C19—C18—H18A	120.4
C11—C7—C6	120.3 (2)	C17—C18—H18A	120.4
C8—C7—C6	121.8 (2)	C18—C19—C14	121.2 (2)
C9—C8—C7	118.9 (2)	C18—C19—H19A	119.4
C9—C8—H8A	120.5	C14—C19—H19A	119.4
C7—C8—H8A	120.5	O1S—C1S—H1S1	109.5
C8—C9—C10	119.0 (2)	O1S—C1S—H1S2	109.5
C8—C9—H9A	120.5	H1S1—C1S—H1S2	109.5
C10—C9—H9A	120.5	O1S—C1S—H1S3	109.5
N2—C10—C9	124.1 (2)	H1S1—C1S—H1S3	109.5
N2—C10—H10A	118.0	H1S2—C1S—H1S3	109.5
C12—N1—C1—C2	0.7 (4)	C6—C7—C11—C12	0.2 (3)
N1—C1—C2—C3	−0.4 (4)	C1—N1—C12—C4	−1.2 (3)
C1—C2—C3—C4	0.4 (4)	C1—N1—C12—C11	179.1 (2)
C2—C3—C4—C12	−0.8 (3)	C3—C4—C12—N1	1.2 (3)
C2—C3—C4—C5	179.2 (2)	C5—C4—C12—N1	−178.7 (2)
C12—C4—C5—C6	0.3 (3)	C3—C4—C12—C11	−179.1 (2)
C3—C4—C5—C6	−179.6 (2)	C5—C4—C12—C11	1.0 (3)
C4—C5—C6—N3	−177.8 (2)	N2—C11—C12—N1	−2.0 (3)
C4—C5—C6—C7	−1.3 (3)	C7—C11—C12—N1	178.5 (2)
C13—N3—C6—C5	−46.2 (3)	N2—C11—C12—C4	178.3 (2)
C13—N3—C6—C7	137.3 (2)	C7—C11—C12—C4	−1.2 (3)
C5—C6—C7—C11	1.1 (3)	C6—N3—C13—C14	176.8 (2)
N3—C6—C7—C11	177.8 (2)	N3—C13—C14—C19	−13.4 (4)
C5—C6—C7—C8	−179.8 (2)	N3—C13—C14—C15	166.3 (2)
N3—C6—C7—C8	−3.1 (3)	C19—C14—C15—O1	178.7 (2)
C11—C7—C8—C9	−1.3 (3)	C13—C14—C15—O1	−1.0 (3)
C6—C7—C8—C9	179.6 (2)	C19—C14—C15—C16	−1.0 (3)
C7—C8—C9—C10	0.3 (4)	C13—C14—C15—C16	179.3 (2)
C11—N2—C10—C9	−0.4 (4)	O1—C15—C16—C17	−179.1 (2)
C8—C9—C10—N2	0.6 (4)	C14—C15—C16—C17	0.7 (4)
C10—N2—C11—C7	−0.7 (3)	C15—C16—C17—C18	−0.3 (4)
C10—N2—C11—C12	179.8 (2)	C16—C17—C18—C19	0.3 (4)
C8—C7—C11—N2	1.6 (3)	C17—C18—C19—C14	−0.7 (4)
C6—C7—C11—N2	−179.3 (2)	C15—C14—C19—C18	1.1 (4)
C8—C7—C11—C12	−178.9 (2)	C13—C14—C19—C18	−179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1S	0.84	1.81	2.640 (3)	172
O1S—H1S···N1i	0.84	2.01	2.829 (3)	163
O1S—H1S···N2i	0.84	2.68	3.242 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1S	0.84	1.81	2.640 (3)	172
O1S—H1S⋯N1i	0.84	2.01	2.829 (3)	163
O1S—H1S⋯N2i	0.84	2.68	3.242 (3)	126

Symmetry code: (i) .