3-(1H-Imidazo[4,5-f][1,10]phenanthrolin-2-yl)benzonitrile methanol solvate.

In the title compound, C(20)H(11)N(5)·CH(3)OH, the benzene ring is twisted by a small dihedral angle of 1.89 (11)° with respect to the imidazo[4,5-f][1,10]phenanthroline ring system. N-H⋯O and O-H⋯N hydrogen bonding is present in the crystal structure.

Related literature

For related structures, see: Sun et al. (2007 ▶); Yin (2008 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C20H11N5·CH4O

M = 353.38

Monoclinic,

a = 7.115 (1) Å

b = 18.385 (2) Å

c = 13.5576 (12) Å

β = 99.956 (19)°

V = 1746.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.28 × 0.26 mm

Data collection

Rigaku, SCXmini diffractometer

15971 measured reflections

3432 independent reflections

2018 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.179

S = 1.04

3432 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); 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, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051472/xu2700sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051472/xu2700Isup2.hkl

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

C20H11N5·CH4O	F(000) = 736
Mr = 353.38	Dx = 1.344 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2018 reflections
a = 7.115 (1) Å	θ = 3.0–26.0°
b = 18.385 (2) Å	µ = 0.09 mm−1
c = 13.5576 (12) Å	T = 293 K
β = 99.956 (19)°	Block, colorless
V = 1746.7 (4) Å3	0.30 × 0.28 × 0.26 mm
Z = 4

Rigaku, SCXmini diffractometer	2018 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.099
graphite	θmax = 26.0°, θmin = 3.0°
Detector resolution: 13.6612 pixels mm-1	h = −8→8
ω scan	k = −22→22
15971 measured reflections	l = −16→16
3432 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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0784P)2 + 0.0647P] where P = (Fo2 + 2Fc2)/3
3432 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.19 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
C1	0.6541 (5)	−0.05805 (18)	0.7761 (3)	0.0518 (8)
C2	0.6702 (4)	−0.07430 (16)	0.6737 (2)	0.0430 (7)
C3	0.6441 (4)	−0.14493 (17)	0.6377 (3)	0.0510 (8)
H3A	0.6173	−0.1822	0.6795	0.061*
C4	0.6581 (5)	−0.15944 (17)	0.5396 (3)	0.0538 (9)
H4A	0.6398	−0.2066	0.5152	0.065*
C5	0.6993 (4)	−0.10430 (17)	0.4769 (2)	0.0501 (8)
H5A	0.7079	−0.1149	0.4107	0.060*
C6	0.7281 (4)	−0.03325 (15)	0.5117 (2)	0.0386 (7)
C7	0.7123 (4)	−0.01864 (16)	0.6113 (2)	0.0407 (7)
H7A	0.7300	0.0285	0.6360	0.049*
C8	0.7695 (4)	0.02402 (15)	0.4435 (2)	0.0391 (7)
C9	0.8262 (4)	0.08115 (15)	0.3144 (2)	0.0388 (7)
C10	0.8600 (4)	0.10077 (16)	0.2162 (2)	0.0391 (7)
C11	0.8394 (4)	0.05275 (17)	0.1346 (2)	0.0490 (8)
H11A	0.7998	0.0051	0.1413	0.059*
C12	0.8787 (5)	0.07721 (19)	0.0448 (2)	0.0567 (9)
H12A	0.8629	0.0470	−0.0110	0.068*
C13	0.9430 (5)	0.14836 (19)	0.0393 (2)	0.0596 (10)
H13A	0.9758	0.1633	−0.0210	0.072*
C14	0.9157 (4)	0.17313 (16)	0.2013 (2)	0.0411 (7)
C15	0.9232 (4)	0.22708 (16)	0.2820 (2)	0.0407 (7)
C16	0.9749 (5)	0.34573 (18)	0.3349 (3)	0.0622 (10)
H16A	1.0103	0.3930	0.3221	0.075*
C17	0.9213 (5)	0.33164 (18)	0.4271 (2)	0.0592 (9)
H17A	0.9197	0.3687	0.4737	0.071*
C18	0.8714 (5)	0.26248 (17)	0.4477 (2)	0.0511 (8)
H18A	0.8365	0.2515	0.5090	0.061*
C19	0.8732 (4)	0.20771 (15)	0.3752 (2)	0.0388 (7)
C20	0.8320 (4)	0.13278 (15)	0.3885 (2)	0.0371 (7)
C21	0.9291 (6)	0.1623 (3)	0.7300 (3)	0.1045 (16)
H21A	0.9003	0.1877	0.7875	0.157*
H21B	1.0353	0.1853	0.7075	0.157*
H21C	0.9610	0.1127	0.7478	0.157*
N1	0.6392 (5)	−0.04524 (19)	0.8570 (2)	0.0749 (9)
N2	0.7870 (3)	0.01301 (12)	0.34899 (16)	0.0406 (6)
N3	0.7950 (3)	0.09555 (12)	0.47126 (17)	0.0390 (6)
H3B	0.7891	0.1137	0.5291	0.047*
N4	0.9610 (4)	0.19635 (14)	0.11301 (19)	0.0550 (7)
N5	0.9787 (4)	0.29620 (13)	0.26399 (19)	0.0513 (7)
O1	0.7700 (4)	0.16399 (13)	0.65327 (16)	0.0640 (7)
H1E	0.6578	0.1781	0.6823	0.14 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.050 (2)	0.061 (2)	0.044 (2)	−0.0024 (16)	0.0072 (16)	0.0113 (16)
C2	0.0349 (16)	0.050 (2)	0.0432 (18)	0.0017 (13)	0.0034 (14)	0.0069 (14)
C3	0.051 (2)	0.0400 (19)	0.063 (2)	−0.0021 (14)	0.0118 (17)	0.0147 (16)
C4	0.055 (2)	0.0383 (19)	0.070 (2)	−0.0027 (14)	0.0155 (18)	−0.0017 (17)
C5	0.0488 (19)	0.050 (2)	0.052 (2)	−0.0018 (15)	0.0117 (16)	−0.0018 (16)
C6	0.0300 (16)	0.0410 (17)	0.0446 (17)	0.0024 (12)	0.0063 (13)	0.0044 (13)
C7	0.0409 (17)	0.0381 (17)	0.0426 (18)	−0.0026 (13)	0.0060 (14)	0.0031 (13)
C8	0.0345 (16)	0.0416 (17)	0.0414 (17)	0.0021 (12)	0.0074 (13)	0.0001 (13)
C9	0.0359 (16)	0.0419 (18)	0.0382 (16)	−0.0003 (12)	0.0051 (13)	0.0016 (13)
C10	0.0351 (16)	0.0460 (18)	0.0361 (16)	0.0024 (13)	0.0062 (13)	−0.0013 (13)
C11	0.053 (2)	0.0483 (19)	0.0457 (19)	0.0018 (15)	0.0095 (16)	−0.0034 (15)
C12	0.070 (2)	0.062 (2)	0.0386 (19)	0.0111 (17)	0.0105 (17)	−0.0064 (16)
C13	0.078 (3)	0.066 (2)	0.0375 (19)	0.0088 (19)	0.0183 (17)	0.0087 (17)
C14	0.0407 (17)	0.0470 (19)	0.0357 (16)	0.0054 (13)	0.0071 (13)	0.0038 (13)
C15	0.0378 (17)	0.0422 (18)	0.0422 (17)	0.0020 (13)	0.0077 (14)	0.0027 (13)
C16	0.087 (3)	0.0392 (19)	0.063 (2)	−0.0115 (17)	0.021 (2)	−0.0003 (17)
C17	0.079 (3)	0.049 (2)	0.052 (2)	−0.0060 (17)	0.0183 (18)	−0.0075 (16)
C18	0.064 (2)	0.049 (2)	0.0429 (18)	−0.0016 (16)	0.0161 (16)	−0.0037 (15)
C19	0.0389 (17)	0.0409 (18)	0.0377 (16)	0.0005 (12)	0.0099 (13)	−0.0005 (13)
C20	0.0347 (16)	0.0436 (18)	0.0345 (16)	0.0030 (12)	0.0103 (13)	0.0041 (13)
C21	0.082 (3)	0.134 (4)	0.092 (3)	0.011 (3)	−0.002 (3)	−0.042 (3)
N1	0.071 (2)	0.100 (3)	0.053 (2)	−0.0063 (18)	0.0090 (17)	0.0078 (18)
N2	0.0423 (15)	0.0424 (15)	0.0386 (14)	−0.0004 (11)	0.0114 (11)	0.0001 (11)
N3	0.0434 (14)	0.0430 (15)	0.0322 (13)	0.0006 (11)	0.0110 (11)	−0.0003 (11)
N4	0.073 (2)	0.0573 (18)	0.0366 (15)	0.0024 (14)	0.0161 (14)	0.0035 (13)
N5	0.0651 (18)	0.0425 (16)	0.0489 (16)	−0.0064 (13)	0.0171 (13)	−0.0016 (12)
O1	0.0695 (17)	0.0778 (17)	0.0474 (14)	0.0083 (13)	0.0177 (13)	−0.0119 (12)

C1—N1	1.145 (4)	C12—H12A	0.9300
C1—C2	1.444 (4)	C13—N4	1.323 (4)
C2—C3	1.388 (4)	C13—H13A	0.9300
C2—C7	1.393 (4)	C14—N4	1.361 (4)
C3—C4	1.376 (4)	C14—C15	1.471 (4)
C3—H3A	0.9300	C15—N5	1.365 (4)
C4—C5	1.387 (4)	C15—C19	1.416 (4)
C4—H4A	0.9300	C16—N5	1.328 (4)
C5—C6	1.392 (4)	C16—C17	1.393 (4)
C5—H5A	0.9300	C16—H16A	0.9300
C6—C7	1.400 (4)	C17—C18	1.362 (4)
C6—C8	1.465 (4)	C17—H17A	0.9300
C7—H7A	0.9300	C18—C19	1.409 (4)
C8—N2	1.324 (3)	C18—H18A	0.9300
C8—N3	1.371 (3)	C19—C20	1.426 (4)
C9—C20	1.378 (4)	C20—N3	1.377 (3)
C9—N2	1.383 (3)	C21—O1	1.400 (4)
C9—C10	1.439 (4)	C21—H21A	0.9600
C10—C11	1.403 (4)	C21—H21B	0.9600
C10—C14	1.412 (4)	C21—H21C	0.9600
C11—C12	1.371 (4)	N3—H3B	0.8600
C11—H11A	0.9300	O1—H1E	0.9842
C12—C13	1.392 (5)
N1—C1—C2	179.2 (4)	C12—C13—H13A	117.4
C3—C2—C7	120.2 (3)	N4—C14—C10	122.4 (3)
C3—C2—C1	120.2 (3)	N4—C14—C15	117.3 (3)
C7—C2—C1	119.5 (3)	C10—C14—C15	120.3 (3)
C4—C3—C2	119.6 (3)	N5—C15—C19	121.3 (3)
C4—C3—H3A	120.2	N5—C15—C14	118.0 (3)
C2—C3—H3A	120.2	C19—C15—C14	120.8 (3)
C3—C4—C5	120.6 (3)	N5—C16—C17	124.4 (3)
C3—C4—H4A	119.7	N5—C16—H16A	117.8
C5—C4—H4A	119.7	C17—C16—H16A	117.8
C4—C5—C6	120.8 (3)	C18—C17—C16	118.6 (3)
C4—C5—H5A	119.6	C18—C17—H17A	120.7
C6—C5—H5A	119.6	C16—C17—H17A	120.7
C5—C6—C7	118.4 (3)	C17—C18—C19	119.3 (3)
C5—C6—C8	119.6 (3)	C17—C18—H18A	120.3
C7—C6—C8	122.0 (3)	C19—C18—H18A	120.3
C2—C7—C6	120.4 (3)	C18—C19—C15	118.5 (3)
C2—C7—H7A	119.8	C18—C19—C20	125.1 (3)
C6—C7—H7A	119.8	C15—C19—C20	116.4 (3)
N2—C8—N3	112.4 (2)	N3—C20—C9	105.4 (2)
N2—C8—C6	124.3 (3)	N3—C20—C19	131.0 (3)
N3—C8—C6	123.2 (3)	C9—C20—C19	123.6 (3)
C20—C9—N2	111.0 (3)	O1—C21—H21A	109.5
C20—C9—C10	120.9 (3)	O1—C21—H21B	109.5
N2—C9—C10	128.1 (3)	H21A—C21—H21B	109.5
C11—C10—C14	118.3 (3)	O1—C21—H21C	109.5
C11—C10—C9	124.1 (3)	H21A—C21—H21C	109.5
C14—C10—C9	117.6 (3)	H21B—C21—H21C	109.5
C12—C11—C10	119.0 (3)	C8—N2—C9	104.4 (2)
C12—C11—H11A	120.5	C8—N3—C20	106.8 (2)
C10—C11—H11A	120.5	C8—N3—H3B	126.6
C11—C12—C13	118.4 (3)	C20—N3—H3B	126.6
C11—C12—H12A	120.8	C13—N4—C14	116.7 (3)
C13—C12—H12A	120.8	C16—N5—C15	117.8 (3)
N4—C13—C12	125.2 (3)	C21—O1—H1E	108.4
N4—C13—H13A	117.4

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O1	0.86	1.95	2.803 (3)	174
O1—H1E···N5i	0.98	1.89	2.857 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯O1	0.86	1.95	2.803 (3)	174
O1—H1E⋯N5i	0.98	1.89	2.857 (3)	168

Symmetry code: (i) .