2-Hydroxy-benzyl alcohol-phenanthroline (1/1).

Crystals of the title compound, C(12)H(8)N(2)·C(7)H(8)O(2), were obtained during cocrystallization experiments of a compound with two hydrogen-bond donors (2-hydroxy-benzyl alcohol) with another compound containing two hydrogen-bond acceptors (phenanthroline). Unexpectedly, the two mol-ecules do not form dimers with two O-H⋯N hydrogen bonds connecting the two mol-ecules. However, one of the hydr-oxy groups forms a bifurcated hydrogen bond to both phenanthroline N atoms, whereas the other hydr-oxy group forms an O-H⋯O hydrogen bond to a symmetry-equivalent 2-hydroxy-benzyl alcohol mol-ecule. In addition, the crystal packing is stabilized by π-π inter-actions between the two phenanthroline ring systems, with a centroid-centroid distance of 3.570  Å.

Related literature

For co-crystallization experiments, see: Ton & Bolte (2005 ▶); Tutughamiarso et al. (2009 ▶).

Experimental

Crystal data

C12H8N2·C7H8O2

M = 304.34

Monoclinic,

a = 7.264 (1) Å

b = 20.256 (3) Å

c = 11.082 (2) Å

β = 109.13 (3)°

V = 1540.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.60 × 0.50 × 0.30 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: none

20425 measured reflections

2885 independent reflections

2518 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.099

S = 1.06

2885 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.21 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044699/om2291sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044699/om2291Isup2.hkl

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

C12H8N2·C7H8O2	F(000) = 640
Mr = 304.34	Dx = 1.312 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11957 reflections
a = 7.264 (1) Å	θ = 3.0–25.0°
b = 20.256 (3) Å	µ = 0.09 mm−1
c = 11.082 (2) Å	T = 173 K
β = 109.13 (3)°	Block, colourless
V = 1540.6 (4) Å3	0.60 × 0.50 × 0.30 mm
Z = 4

Stoe IPDS II two-circle diffractometer	2518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 25.7°, θmin = 2.8°
ω scans	h = −8→8
20425 measured reflections	k = −24→24
2885 independent reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.2526P] where P = (Fo2 + 2Fc2)/3
2885 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.21 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
N1	0.68091 (17)	0.08958 (5)	0.49625 (11)	0.0357 (3)
N2	0.89787 (17)	0.03273 (5)	0.72184 (11)	0.0371 (3)
C1	0.72912 (18)	0.02470 (6)	0.49544 (13)	0.0330 (3)
C2	0.5740 (2)	0.11589 (7)	0.38637 (14)	0.0418 (3)
H2	0.5403	0.1612	0.3860	0.050*
C3	0.5071 (2)	0.08146 (8)	0.27060 (15)	0.0478 (4)
H3	0.4303	0.1029	0.1945	0.057*
C4	0.5553 (2)	0.01591 (8)	0.26982 (15)	0.0477 (4)
H4	0.5114	−0.0087	0.1927	0.057*
C5	0.6694 (2)	−0.01440 (7)	0.38328 (14)	0.0398 (3)
C6	0.7275 (2)	−0.08270 (7)	0.38997 (17)	0.0480 (4)
H6	0.6881	−0.1088	0.3146	0.058*
C7	0.8361 (2)	−0.11014 (7)	0.50050 (18)	0.0497 (4)
H7	0.8733	−0.1552	0.5017	0.060*
C8	0.8973 (2)	−0.07275 (6)	0.61706 (15)	0.0406 (3)
C9	1.0057 (2)	−0.10017 (7)	0.73516 (18)	0.0513 (4)
H9	1.0437	−0.1452	0.7402	0.062*
C10	1.0568 (2)	−0.06217 (8)	0.84299 (18)	0.0526 (4)
H10	1.1285	−0.0803	0.9238	0.063*
C11	1.0001 (2)	0.00436 (7)	0.83078 (15)	0.0459 (4)
H11	1.0376	0.0308	0.9057	0.055*
C12	0.84467 (19)	−0.00511 (6)	0.61498 (13)	0.0342 (3)
O1	0.96385 (12)	0.19916 (5)	0.97867 (8)	0.0343 (2)
H1O	0.9040	0.1823	0.8970	0.051*
O2	1.25869 (12)	0.33737 (4)	1.24759 (8)	0.0299 (2)
H2O	1.2750	0.3699	1.2006	0.045*
C13	1.16077 (16)	0.20302 (6)	1.00360 (11)	0.0254 (3)
C14	1.26346 (16)	0.24552 (6)	1.10244 (11)	0.0252 (3)
C15	1.46410 (17)	0.25043 (6)	1.13083 (12)	0.0300 (3)
H15	1.5363	0.2785	1.1984	0.036*
C16	1.56203 (18)	0.21500 (6)	1.06219 (13)	0.0333 (3)
H16	1.6992	0.2192	1.0829	0.040*
C17	1.45820 (18)	0.17387 (6)	0.96403 (12)	0.0325 (3)
H17	1.5239	0.1501	0.9164	0.039*
C18	1.25733 (18)	0.16711 (6)	0.93473 (12)	0.0293 (3)
H18	1.1863	0.1382	0.8682	0.035*
C19	1.15095 (17)	0.28505 (6)	1.17128 (11)	0.0297 (3)
H19A	1.0333	0.3037	1.1071	0.036*
H19B	1.1069	0.2548	1.2265	0.036*

	U11	U22	U33	U12	U13	U23
N1	0.0415 (6)	0.0277 (5)	0.0471 (7)	−0.0037 (5)	0.0269 (5)	−0.0039 (5)
N2	0.0471 (7)	0.0279 (6)	0.0456 (7)	−0.0038 (5)	0.0277 (5)	−0.0007 (5)
C1	0.0352 (7)	0.0267 (6)	0.0486 (8)	−0.0082 (5)	0.0295 (6)	−0.0070 (5)
C2	0.0450 (8)	0.0384 (8)	0.0490 (8)	−0.0024 (6)	0.0248 (7)	0.0022 (6)
C3	0.0454 (8)	0.0580 (10)	0.0469 (8)	−0.0112 (7)	0.0244 (7)	0.0013 (7)
C4	0.0474 (8)	0.0588 (10)	0.0470 (8)	−0.0211 (7)	0.0293 (7)	−0.0152 (7)
C5	0.0415 (7)	0.0374 (7)	0.0552 (9)	−0.0164 (6)	0.0356 (7)	−0.0155 (6)
C6	0.0556 (9)	0.0368 (8)	0.0695 (11)	−0.0192 (7)	0.0449 (9)	−0.0242 (7)
C7	0.0539 (9)	0.0247 (7)	0.0892 (13)	−0.0095 (6)	0.0490 (9)	−0.0169 (7)
C8	0.0388 (7)	0.0240 (6)	0.0719 (10)	−0.0049 (5)	0.0357 (7)	−0.0035 (6)
C9	0.0459 (8)	0.0278 (7)	0.0909 (13)	0.0019 (6)	0.0371 (9)	0.0081 (8)
C10	0.0484 (9)	0.0439 (8)	0.0702 (11)	0.0004 (7)	0.0257 (8)	0.0165 (8)
C11	0.0534 (9)	0.0402 (8)	0.0509 (9)	−0.0057 (6)	0.0263 (7)	0.0027 (6)
C12	0.0365 (7)	0.0250 (6)	0.0538 (8)	−0.0066 (5)	0.0321 (6)	−0.0056 (5)
O1	0.0208 (4)	0.0510 (6)	0.0310 (5)	−0.0017 (4)	0.0083 (3)	−0.0068 (4)
O2	0.0376 (5)	0.0240 (4)	0.0281 (4)	−0.0015 (3)	0.0108 (4)	0.0035 (3)
C13	0.0224 (5)	0.0288 (6)	0.0254 (6)	0.0018 (4)	0.0084 (4)	0.0058 (5)
C14	0.0248 (6)	0.0253 (6)	0.0264 (6)	0.0022 (4)	0.0094 (5)	0.0061 (5)
C15	0.0254 (6)	0.0291 (6)	0.0349 (6)	−0.0022 (5)	0.0090 (5)	0.0024 (5)
C16	0.0232 (6)	0.0341 (7)	0.0446 (7)	0.0017 (5)	0.0138 (5)	0.0059 (6)
C17	0.0323 (6)	0.0325 (6)	0.0380 (7)	0.0079 (5)	0.0188 (5)	0.0061 (5)
C18	0.0304 (6)	0.0299 (6)	0.0283 (6)	0.0024 (5)	0.0105 (5)	0.0016 (5)
C19	0.0263 (6)	0.0326 (6)	0.0311 (6)	−0.0018 (5)	0.0104 (5)	−0.0024 (5)

N1—C2	1.3230 (19)	C10—C11	1.403 (2)
N1—C1	1.3609 (17)	C10—H10	0.9500
N2—C11	1.3235 (19)	C11—H11	0.9500
N2—C12	1.3562 (17)	O1—C13	1.3674 (14)
C1—C5	1.4166 (19)	O1—H1O	0.9310
C1—C12	1.448 (2)	O2—C19	1.4203 (15)
C2—C3	1.400 (2)	O2—H2O	0.8714
C2—H2	0.9500	C13—C18	1.3980 (17)
C3—C4	1.374 (2)	C13—C14	1.4006 (17)
C3—H3	0.9500	C14—C15	1.3901 (17)
C4—C5	1.401 (2)	C14—C19	1.5165 (16)
C4—H4	0.9500	C15—C16	1.3979 (18)
C5—C6	1.441 (2)	C15—H15	0.9500
C6—C7	1.341 (2)	C16—C17	1.3816 (19)
C6—H6	0.9500	C16—H16	0.9500
C7—C8	1.437 (2)	C17—C18	1.3938 (18)
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.402 (2)	C18—H18	0.9500
C8—C12	1.4206 (18)	C19—H19A	0.9900
C9—C10	1.366 (3)	C19—H19B	0.9900
C9—H9	0.9500
C2—N1—C1	117.24 (12)	N2—C11—C10	124.36 (15)
C11—N2—C12	117.73 (12)	N2—C11—H11	117.8
N1—C1—C5	122.70 (13)	C10—C11—H11	117.8
N1—C1—C12	118.04 (12)	N2—C12—C8	122.19 (13)
C5—C1—C12	119.26 (12)	N2—C12—C1	118.51 (11)
N1—C2—C3	124.43 (14)	C8—C12—C1	119.30 (12)
N1—C2—H2	117.8	C13—O1—H1O	110.0
C3—C2—H2	117.8	C19—O2—H2O	111.4
C4—C3—C2	118.34 (15)	O1—C13—C18	122.60 (11)
C4—C3—H3	120.8	O1—C13—C14	116.55 (10)
C2—C3—H3	120.8	C18—C13—C14	120.85 (11)
C3—C4—C5	119.67 (14)	C15—C14—C13	118.11 (11)
C3—C4—H4	120.2	C15—C14—C19	123.11 (11)
C5—C4—H4	120.2	C13—C14—C19	118.77 (10)
C4—C5—C1	117.62 (13)	C14—C15—C16	121.53 (12)
C4—C5—C6	122.97 (14)	C14—C15—H15	119.2
C1—C5—C6	119.42 (15)	C16—C15—H15	119.2
C7—C6—C5	121.31 (14)	C17—C16—C15	119.61 (11)
C7—C6—H6	119.3	C17—C16—H16	120.2
C5—C6—H6	119.3	C15—C16—H16	120.2
C6—C7—C8	121.26 (13)	C16—C17—C18	120.15 (11)
C6—C7—H7	119.4	C16—C17—H17	119.9
C8—C7—H7	119.4	C18—C17—H17	119.9
C9—C8—C12	117.59 (14)	C17—C18—C13	119.73 (12)
C9—C8—C7	122.96 (14)	C17—C18—H18	120.1
C12—C8—C7	119.44 (14)	C13—C18—H18	120.1
C10—C9—C8	120.10 (14)	O2—C19—C14	114.26 (10)
C10—C9—H9	119.9	O2—C19—H19A	108.7
C8—C9—H9	119.9	C14—C19—H19A	108.7
C9—C10—C11	118.03 (16)	O2—C19—H19B	108.7
C9—C10—H10	121.0	C14—C19—H19B	108.7
C11—C10—H10	121.0	H19A—C19—H19B	107.6
C2—N1—C1—C5	−0.08 (18)	C11—N2—C12—C1	178.66 (11)
C2—N1—C1—C12	−179.49 (11)	C9—C8—C12—N2	0.86 (18)
C1—N1—C2—C3	0.4 (2)	C7—C8—C12—N2	179.91 (11)
N1—C2—C3—C4	−0.2 (2)	C9—C8—C12—C1	−178.65 (11)
C2—C3—C4—C5	−0.3 (2)	C7—C8—C12—C1	0.40 (18)
C3—C4—C5—C1	0.55 (19)	N1—C1—C12—N2	0.52 (17)
C3—C4—C5—C6	−179.40 (13)	C5—C1—C12—N2	−178.92 (10)
N1—C1—C5—C4	−0.37 (18)	N1—C1—C12—C8	−179.96 (11)
C12—C1—C5—C4	179.04 (11)	C5—C1—C12—C8	0.61 (17)
N1—C1—C5—C6	179.58 (11)	O1—C13—C14—C15	179.69 (10)
C12—C1—C5—C6	−1.02 (17)	C18—C13—C14—C15	−0.63 (17)
C4—C5—C6—C7	−179.66 (13)	O1—C13—C14—C19	−1.68 (15)
C1—C5—C6—C7	0.40 (19)	C18—C13—C14—C19	178.01 (11)
C5—C6—C7—C8	0.6 (2)	C13—C14—C15—C16	0.95 (17)
C6—C7—C8—C9	177.95 (13)	C19—C14—C15—C16	−177.62 (11)
C6—C7—C8—C12	−1.0 (2)	C14—C15—C16—C17	−0.24 (19)
C12—C8—C9—C10	0.1 (2)	C15—C16—C17—C18	−0.81 (18)
C7—C8—C9—C10	−178.94 (13)	C16—C17—C18—C13	1.12 (18)
C8—C9—C10—C11	−0.9 (2)	O1—C13—C18—C17	179.27 (11)
C12—N2—C11—C10	−0.1 (2)	C14—C13—C18—C17	−0.39 (17)
C9—C10—C11—N2	1.0 (2)	C15—C14—C19—O2	12.73 (16)
C11—N2—C12—C8	−0.86 (18)	C13—C14—C19—O2	−165.84 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2i	0.93	1.69	2.6125 (14)	168
O2—H2O···N1ii	0.87	2.29	3.0390 (15)	144
O2—H2O···N2ii	0.87	2.15	2.8663 (14)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2i	0.93	1.69	2.6125 (14)	168
O2—H2O⋯N1ii	0.87	2.29	3.0390 (15)	144
O2—H2O⋯N2ii	0.87	2.15	2.8663 (14)	140

Symmetry codes: (i) ; (ii) .