1,10-Phenanthroline-5,6-dione ethanol monosolvate.

In the title compound, C12H6N2O2·C2H5OH, the mol-ecule of the 1,10-phenanthroline-5,6-dione is approximately planar, with a maximum deviation of 0.051 (1) Å. In the crystal, mol-ecules are linked by O-H⋯N and weak C-H⋯O hydrogen bonds, forming supra-molecular chains propagating along [110]. π-π stacking inter-actions are observed between the pyridine rings of neighbouring chains, the centroid-centroid separations being 3.6226 (11) and 3.7543 (11) Å.

Related literature

For background to and applications of 1,10-phenanthroline-5,6-dione, see: Smith & Cagle (1947 ▶); Ma et al. (2010 ▶); Goss & Abruna (1985 ▶); Murphy et al. (2011 ▶); Wu et al. (1996 ▶); Pinczewska et al. (2012 ▶); Poteet & MacDonnell (2013 ▶); Wu et al. (2002 ▶); Poteet et al. 2013 ▶); Paw et al. (1998 ▶). For the synthesis, see: Paw & Eisenberg (1997 ▶). For a related structure, see: Calderazzo et al. (1999 ▶).

Experimental

Crystal data

C12H6N2O2·C2H6O

M = 256.26

Triclinic,

a = 7.3064 (15) Å

b = 9.1055 (18) Å

c = 9.7291 (19) Å

α = 96.47 (3)°

β = 101.68 (3)°

γ = 109.83 (3)°

V = 584.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 123 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn724+ diffractometer

5059 measured reflections

2252 independent reflections

2074 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.114

S = 1.06

2252 reflections

185 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814008241/xu5783sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008241/xu5783Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008241/xu5783Isup3.cml

CCDC reference: 996896

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H6N2O2·C2H6O	Z = 2
Mr = 256.26	F(000) = 268
Triclinic, P1	Dx = 1.456 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3064 (15) Å	Cell parameters from 2355 reflections
b = 9.1055 (18) Å	θ = 3.1–30.2°
c = 9.7291 (19) Å	µ = 0.10 mm−1
α = 96.47 (3)°	T = 123 K
β = 101.68 (3)°	Block, yellow
γ = 109.83 (3)°	0.20 × 0.20 × 0.20 mm
V = 584.6 (2) Å3

Rigaku Saturn724+ diffractometer	2074 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.020
Confocal monochromator	θmax = 26.0°, θmin = 3.1°
Detector resolution: 28.5714 pixels mm-1	h = −9→9
ω scans	k = −11→11
5059 measured reflections	l = −11→11
2252 independent reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0709P)2 + 0.118P] where P = (Fo2 + 2Fc2)/3
2252 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.24 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

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
C4	0.66468 (17)	0.96363 (14)	0.27101 (12)	0.0211 (3)
C11	0.69855 (17)	0.93910 (13)	0.52865 (12)	0.0196 (3)
C5	0.50156 (18)	0.80403 (14)	0.22423 (12)	0.0237 (3)
C7	0.54977 (17)	0.78514 (14)	0.49173 (12)	0.0211 (3)
C6	0.43997 (17)	0.70995 (13)	0.34035 (13)	0.0239 (3)
C12	0.75757 (16)	1.02974 (13)	0.41609 (12)	0.0200 (3)
C8	0.50365 (18)	0.70329 (14)	0.60099 (13)	0.0250 (3)
H8	0.4042	0.5987	0.5794	0.030*
C9	0.60544 (18)	0.77748 (15)	0.74108 (13)	0.0270 (3)
H9	0.5787	0.7248	0.8179	0.032*
C3	0.72616 (18)	1.05260 (15)	0.16952 (13)	0.0252 (3)
H3	0.6651	1.0108	0.0704	0.030*
C1	0.95979 (18)	1.25750 (14)	0.36088 (14)	0.0262 (3)
H1	1.0632	1.3603	0.3919	0.031*
C10	0.74812 (18)	0.93131 (15)	0.76688 (13)	0.0261 (3)
H10	0.8166	0.9818	0.8636	0.031*
C2	0.87625 (19)	1.20164 (15)	0.21448 (14)	0.0272 (3)
H2	0.9213	1.2644	0.1475	0.033*
O1	0.41332 (14)	0.74720 (11)	0.09901 (9)	0.0331 (3)
O2	0.30275 (14)	0.58111 (10)	0.30567 (10)	0.0333 (3)
N2	0.79532 (15)	1.01274 (12)	0.66490 (10)	0.0237 (2)
N1	0.90359 (15)	1.17542 (12)	0.46054 (11)	0.0233 (2)
C15	0.8686 (2)	0.65765 (16)	0.07549 (14)	0.0336 (3)
H15A	0.8325	0.7503	0.0621	0.050*
H15B	0.8372	0.5885	−0.0177	0.050*
H15C	1.0130	0.6934	0.1211	0.050*
C14	0.7508 (2)	0.56671 (15)	0.16901 (14)	0.0312 (3)
O3	0.76490 (13)	0.66129 (10)	0.30034 (9)	0.0291 (2)
H14A	0.598 (3)	0.5214 (19)	0.1167 (17)	0.042 (4)*
H14B	0.797 (3)	0.479 (2)	0.1910 (18)	0.048 (5)*
H3O	0.8864 (17)	0.719 (2)	0.3431 (19)	0.058 (5)*

	U11	U22	U33	U12	U13	U23
C4	0.0190 (6)	0.0245 (6)	0.0236 (6)	0.0108 (5)	0.0073 (4)	0.0073 (5)
C11	0.0173 (5)	0.0214 (6)	0.0226 (6)	0.0091 (4)	0.0069 (4)	0.0051 (4)
C5	0.0215 (6)	0.0259 (6)	0.0238 (6)	0.0102 (5)	0.0044 (5)	0.0036 (5)
C7	0.0188 (6)	0.0219 (6)	0.0252 (6)	0.0091 (5)	0.0077 (4)	0.0064 (4)
C6	0.0205 (6)	0.0222 (6)	0.0291 (6)	0.0078 (5)	0.0068 (5)	0.0043 (5)
C12	0.0168 (5)	0.0216 (6)	0.0238 (6)	0.0086 (4)	0.0070 (4)	0.0053 (4)
C8	0.0217 (6)	0.0231 (6)	0.0330 (7)	0.0085 (5)	0.0107 (5)	0.0100 (5)
C9	0.0266 (6)	0.0333 (7)	0.0277 (6)	0.0138 (5)	0.0118 (5)	0.0145 (5)
C3	0.0242 (6)	0.0326 (7)	0.0240 (6)	0.0143 (5)	0.0085 (5)	0.0095 (5)
C1	0.0215 (6)	0.0234 (6)	0.0355 (7)	0.0065 (5)	0.0113 (5)	0.0107 (5)
C10	0.0260 (6)	0.0332 (7)	0.0215 (6)	0.0124 (5)	0.0077 (5)	0.0069 (5)
C2	0.0268 (6)	0.0324 (7)	0.0318 (7)	0.0150 (5)	0.0157 (5)	0.0163 (5)
O1	0.0338 (5)	0.0333 (5)	0.0238 (5)	0.0072 (4)	0.0005 (4)	0.0019 (4)
O2	0.0290 (5)	0.0249 (5)	0.0346 (5)	−0.0012 (4)	0.0051 (4)	0.0027 (4)
N2	0.0234 (5)	0.0257 (5)	0.0222 (5)	0.0088 (4)	0.0070 (4)	0.0044 (4)
N1	0.0200 (5)	0.0223 (5)	0.0276 (5)	0.0068 (4)	0.0076 (4)	0.0060 (4)
C15	0.0321 (7)	0.0332 (7)	0.0282 (7)	0.0040 (5)	0.0083 (5)	0.0019 (5)
C14	0.0388 (8)	0.0250 (6)	0.0296 (7)	0.0104 (5)	0.0116 (6)	0.0043 (5)
O3	0.0255 (5)	0.0329 (5)	0.0261 (5)	0.0092 (4)	0.0059 (4)	0.0007 (4)

C4—C3	1.3950 (17)	C3—C2	1.3776 (19)
C4—C12	1.3995 (17)	C3—H3	0.9500
C4—C5	1.4818 (18)	C1—N1	1.3355 (16)
C11—N2	1.3436 (16)	C1—C2	1.3907 (18)
C11—C7	1.4037 (17)	C1—H1	0.9500
C11—C12	1.4899 (16)	C10—N2	1.3357 (16)
C5—O1	1.2171 (15)	C10—H10	0.9500
C5—C6	1.5411 (17)	C2—H2	0.9500
C7—C8	1.3972 (17)	C15—C14	1.5026 (18)
C7—C6	1.4843 (18)	C15—H15A	0.9800
C6—O2	1.2128 (16)	C15—H15B	0.9800
C12—N1	1.3448 (16)	C15—H15C	0.9800
C8—C9	1.3813 (18)	C14—O3	1.4225 (15)
C8—H8	0.9500	C14—H14A	1.040 (18)
C9—C10	1.3914 (19)	C14—H14B	0.995 (18)
C9—H9	0.9500	O3—H3O	0.850 (10)
C3—C4—C12	118.58 (11)	C4—C3—H3	120.3
C3—C4—C5	119.93 (11)	N1—C1—C2	124.01 (11)
C12—C4—C5	121.48 (11)	N1—C1—H1	118.0
N2—C11—C7	122.79 (11)	C2—C1—H1	118.0
N2—C11—C12	116.36 (10)	N2—C10—C9	124.42 (12)
C7—C11—C12	120.85 (11)	N2—C10—H10	117.8
O1—C5—C4	122.47 (12)	C9—C10—H10	117.8
O1—C5—C6	119.54 (11)	C3—C2—C1	117.99 (11)
C4—C5—C6	117.97 (10)	C3—C2—H2	121.0
C8—C7—C11	118.69 (11)	C1—C2—H2	121.0
C8—C7—C6	119.96 (11)	C10—N2—C11	117.08 (11)
C11—C7—C6	121.35 (11)	C1—N1—C12	117.77 (11)
O2—C6—C7	122.90 (12)	C14—C15—H15A	109.5
O2—C6—C5	119.48 (11)	C14—C15—H15B	109.5
C7—C6—C5	117.60 (10)	H15A—C15—H15B	109.5
N1—C12—C4	122.28 (11)	C14—C15—H15C	109.5
N1—C12—C11	117.04 (10)	H15A—C15—H15C	109.5
C4—C12—C11	120.68 (11)	H15B—C15—H15C	109.5
C9—C8—C7	118.69 (11)	O3—C14—C15	114.19 (11)
C9—C8—H8	120.7	O3—C14—H14A	104.6 (9)
C7—C8—H8	120.7	C15—C14—H14A	109.3 (9)
C8—C9—C10	118.31 (11)	O3—C14—H14B	108.5 (10)
C8—C9—H9	120.8	C15—C14—H14B	109.8 (10)
C10—C9—H9	120.8	H14A—C14—H14B	110.5 (14)
C2—C3—C4	119.37 (12)	C14—O3—H3O	111.5 (14)
C2—C3—H3	120.3

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···N1i	0.85 (1)	2.08 (1)	2.8258 (19)	146 (2)
C1—H1···O2ii	0.95	2.53	3.3381 (19)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯N1i	0.85 (1)	2.08 (1)	2.8258 (19)	146 (2)
C1—H1⋯O2ii	0.95	2.53	3.3381 (19)	143

Symmetry codes: (i) ; (ii) .