2-(4-Methyl-phen-yl)-1H-imidazo[4,5-f][1,10]phenanthroline.

In the title compound, C(20)H(14)N(4), all the non-H atoms are roughly coplanar with an r.m.s. deviation of 0.0776 Å. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, forming chains along the ([Formula: see text]). The chains are connected by inter-molecular C-H⋯N hydrogen bonds and π-π stacking inter-actions between inversion-related phenanthroline, imidazole and phenyl rings with centroid-centroid distances in the range 3.777 (1)-3.905 (1) Å.

Related literature

For the biological activity of complexes of metal ions with 1,10-phenanthroline and its derivatives, see: Gao et al. (2009 ▶); Lu et al. (2003 ▶); Yuan et al. (2009 ▶, 2010 ▶); Chen et al. (2010 ▶). For aromatic π–π stacking inter­actions in related structures, see: Lu et al. (2004a ▶,b ▶,c ▶,d ▶); Ma et al. (2010 ▶); Ye et al. (2005 ▶); Zhang et al. (2005 ▶).

Experimental

Crystal data

C20H14N4

M = 310.35

Monoclinic,

a = 9.1609 (8) Å

b = 15.5398 (13) Å

c = 11.725 (1) Å

β = 108.892 (1)°

V = 1579.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.976, T max = 0.984

10917 measured reflections

2790 independent reflections

2182 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.05

2790 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008853/lw2058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008853/lw2058Isup2.hkl

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

C20H14N4	F(000) = 648
Mr = 310.35	Dx = 1.305 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4474 reflections
a = 9.1609 (8) Å	θ = 2.5–27.4°
b = 15.5398 (13) Å	µ = 0.08 mm−1
c = 11.725 (1) Å	T = 298 K
β = 108.892 (1)°	Block, yellow
V = 1579.2 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART 1K CCD area-detector diffractometer	2790 independent reflections
Radiation source: fine-focus sealed tube	2182 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→10
Tmin = 0.976, Tmax = 0.984	k = −18→18
10917 measured 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.047P)2 + 0.4106P] where P = (Fo2 + 2Fc2)/3
2790 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.16 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	0.1494 (2)	0.34388 (11)	0.29392 (16)	0.0569 (5)
H1	0.0796	0.3893	0.2775	0.068*
C2	0.2314 (2)	0.32622 (12)	0.41361 (15)	0.0600 (5)
H2	0.2142	0.3582	0.4751	0.072*
C3	0.3377 (2)	0.26132 (11)	0.43997 (14)	0.0497 (4)
H3	0.3958	0.2495	0.5195	0.060*
C4	0.35793 (17)	0.21310 (9)	0.34572 (13)	0.0394 (4)
C5	0.26563 (18)	0.23316 (10)	0.22634 (13)	0.0413 (4)
C6	0.27420 (18)	0.18067 (10)	0.12531 (13)	0.0424 (4)
C7	0.37132 (17)	0.10795 (10)	0.14623 (13)	0.0405 (4)
C8	0.3685 (2)	0.05668 (11)	0.04748 (14)	0.0506 (4)
H8	0.4290	0.0073	0.0587	0.061*
C9	0.2767 (2)	0.07936 (12)	−0.06532 (15)	0.0607 (5)
H9	0.2740	0.0464	−0.1321	0.073*
C10	0.1872 (2)	0.15308 (12)	−0.07761 (15)	0.0635 (5)
H10	0.1256	0.1686	−0.1548	0.076*
C11	0.46288 (17)	0.14274 (10)	0.36043 (13)	0.0386 (4)
C12	0.46786 (17)	0.09098 (10)	0.26710 (13)	0.0390 (4)
C13	0.63601 (17)	0.04011 (10)	0.42481 (13)	0.0415 (4)
C14	0.76079 (17)	−0.01205 (10)	0.50460 (13)	0.0433 (4)
C15	0.8293 (2)	−0.07558 (12)	0.45554 (16)	0.0549 (5)
H15	0.7935	−0.0854	0.3728	0.066*
C16	0.9495 (2)	−0.12424 (13)	0.52785 (17)	0.0615 (5)
H16	0.9942	−0.1658	0.4926	0.074*
C17	1.0053 (2)	−0.11301 (13)	0.65087 (16)	0.0567 (5)
C18	0.9361 (2)	−0.05052 (13)	0.69982 (16)	0.0600 (5)
H18	0.9709	−0.0419	0.7828	0.072*
C19	0.8162 (2)	−0.00045 (12)	0.62845 (15)	0.0538 (4)
H19	0.7725	0.0414	0.6639	0.065*
C20	1.1369 (2)	−0.16699 (15)	0.7291 (2)	0.0798 (7)
H20A	1.2040	−0.1317	0.7914	0.120*
H20B	1.1938	−0.1907	0.6806	0.120*
H20C	1.0966	−0.2129	0.7649	0.120*
N1	0.16445 (16)	0.29995 (9)	0.20174 (12)	0.0501 (4)
N2	0.18375 (17)	0.20271 (9)	0.01305 (12)	0.0560 (4)
N3	0.57503 (14)	0.02646 (8)	0.30708 (11)	0.0433 (3)
N4	0.57054 (15)	0.10950 (8)	0.46160 (11)	0.0416 (3)
H4	0.603 (2)	0.1350 (12)	0.5353 (17)	0.062 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0703 (12)	0.0485 (10)	0.0497 (10)	0.0146 (9)	0.0165 (9)	−0.0020 (8)
C2	0.0797 (13)	0.0563 (11)	0.0439 (10)	0.0147 (10)	0.0200 (9)	−0.0059 (8)
C3	0.0604 (10)	0.0491 (10)	0.0365 (8)	0.0031 (8)	0.0114 (7)	−0.0023 (7)
C4	0.0447 (8)	0.0365 (8)	0.0354 (8)	−0.0045 (7)	0.0107 (6)	−0.0015 (6)
C5	0.0469 (9)	0.0372 (8)	0.0377 (8)	−0.0005 (7)	0.0109 (7)	0.0004 (7)
C6	0.0481 (9)	0.0423 (9)	0.0338 (8)	0.0009 (7)	0.0089 (7)	0.0007 (7)
C7	0.0453 (9)	0.0412 (9)	0.0350 (8)	−0.0010 (7)	0.0130 (7)	0.0015 (6)
C8	0.0608 (10)	0.0507 (10)	0.0394 (9)	0.0100 (8)	0.0151 (8)	−0.0014 (7)
C9	0.0787 (13)	0.0637 (12)	0.0359 (9)	0.0129 (10)	0.0132 (8)	−0.0062 (8)
C10	0.0787 (13)	0.0678 (12)	0.0337 (9)	0.0174 (10)	0.0041 (8)	−0.0004 (8)
C11	0.0414 (8)	0.0388 (8)	0.0333 (8)	−0.0042 (7)	0.0089 (6)	0.0016 (6)
C12	0.0409 (8)	0.0391 (8)	0.0356 (8)	−0.0011 (7)	0.0104 (6)	0.0019 (6)
C13	0.0436 (8)	0.0417 (9)	0.0386 (8)	−0.0032 (7)	0.0127 (7)	0.0035 (7)
C14	0.0424 (8)	0.0460 (9)	0.0404 (8)	−0.0031 (7)	0.0120 (7)	0.0083 (7)
C15	0.0595 (11)	0.0585 (11)	0.0448 (9)	0.0087 (9)	0.0140 (8)	0.0092 (8)
C16	0.0611 (11)	0.0623 (12)	0.0620 (12)	0.0133 (9)	0.0213 (9)	0.0146 (9)
C17	0.0461 (9)	0.0642 (12)	0.0578 (11)	0.0003 (9)	0.0139 (8)	0.0233 (9)
C18	0.0540 (10)	0.0757 (13)	0.0432 (10)	−0.0034 (9)	0.0060 (8)	0.0141 (9)
C19	0.0533 (10)	0.0617 (11)	0.0443 (9)	0.0007 (8)	0.0126 (8)	0.0055 (8)
C20	0.0587 (12)	0.0927 (16)	0.0806 (15)	0.0122 (11)	0.0124 (11)	0.0390 (13)
N1	0.0613 (9)	0.0434 (8)	0.0418 (8)	0.0089 (7)	0.0114 (6)	0.0003 (6)
N2	0.0698 (10)	0.0544 (9)	0.0355 (7)	0.0137 (7)	0.0054 (7)	0.0003 (6)
N3	0.0457 (7)	0.0438 (8)	0.0379 (7)	0.0023 (6)	0.0099 (6)	0.0027 (6)
N4	0.0463 (7)	0.0417 (8)	0.0327 (7)	−0.0028 (6)	0.0070 (6)	−0.0001 (6)

C1—N1	1.323 (2)	C11—C12	1.371 (2)
C1—C2	1.388 (2)	C11—N4	1.3744 (19)
C1—H1	0.9300	C12—N3	1.3751 (19)
C2—C3	1.366 (2)	C13—N3	1.3278 (19)
C2—H2	0.9300	C13—N4	1.370 (2)
C3—C4	1.396 (2)	C13—C14	1.465 (2)
C3—H3	0.9300	C14—C19	1.386 (2)
C4—C5	1.416 (2)	C14—C15	1.390 (2)
C4—C11	1.429 (2)	C15—C16	1.378 (2)
C5—N1	1.359 (2)	C15—H15	0.9300
C5—C6	1.461 (2)	C16—C17	1.376 (3)
C6—N2	1.3528 (19)	C16—H16	0.9300
C6—C7	1.410 (2)	C17—C18	1.382 (3)
C7—C8	1.399 (2)	C17—C20	1.511 (2)
C7—C12	1.431 (2)	C18—C19	1.384 (2)
C8—C9	1.364 (2)	C18—H18	0.9300
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.389 (3)	C20—H20A	0.9600
C9—H9	0.9300	C20—H20B	0.9600
C10—N2	1.322 (2)	C20—H20C	0.9600
C10—H10	0.9300	N4—H4	0.908 (19)
N1—C1—C2	123.95 (16)	N3—C12—C7	128.03 (13)
N1—C1—H1	118.0	N3—C13—N4	111.93 (13)
C2—C1—H1	118.0	N3—C13—C14	123.65 (14)
C3—C2—C1	119.18 (16)	N4—C13—C14	124.41 (14)
C3—C2—H2	120.4	C19—C14—C15	117.68 (15)
C1—C2—H2	120.4	C19—C14—C13	122.85 (16)
C2—C3—C4	118.99 (15)	C15—C14—C13	119.47 (14)
C2—C3—H3	120.5	C16—C15—C14	120.86 (17)
C4—C3—H3	120.5	C16—C15—H15	119.6
C3—C4—C5	118.32 (14)	C14—C15—H15	119.6
C3—C4—C11	124.86 (14)	C17—C16—C15	121.78 (19)
C5—C4—C11	116.79 (13)	C17—C16—H16	119.1
N1—C5—C4	121.73 (14)	C15—C16—H16	119.1
N1—C5—C6	117.80 (13)	C16—C17—C18	117.37 (16)
C4—C5—C6	120.46 (14)	C16—C17—C20	121.20 (19)
N2—C6—C7	121.69 (14)	C18—C17—C20	121.43 (18)
N2—C6—C5	118.08 (14)	C17—C18—C19	121.64 (17)
C7—C6—C5	120.20 (13)	C17—C18—H18	119.2
C8—C7—C6	118.11 (14)	C19—C18—H18	119.2
C8—C7—C12	123.68 (14)	C18—C19—C14	120.66 (18)
C6—C7—C12	118.22 (13)	C18—C19—H19	119.7
C9—C8—C7	119.71 (16)	C14—C19—H19	119.7
C9—C8—H8	120.1	C17—C20—H20A	109.5
C7—C8—H8	120.1	C17—C20—H20B	109.5
C8—C9—C10	118.15 (16)	H20A—C20—H20B	109.5
C8—C9—H9	120.9	C17—C20—H20C	109.5
C10—C9—H9	120.9	H20A—C20—H20C	109.5
N2—C10—C9	124.39 (16)	H20B—C20—H20C	109.5
N2—C10—H10	117.8	C1—N1—C5	117.73 (14)
C9—C10—H10	117.8	C10—N2—C6	117.91 (15)
C12—C11—N4	105.57 (13)	C13—N3—C12	104.57 (13)
C12—C11—C4	123.21 (13)	C13—N4—C11	106.80 (13)
N4—C11—C4	131.17 (14)	C13—N4—H4	127.0 (12)
C11—C12—N3	111.12 (13)	C11—N4—H4	125.3 (12)
C11—C12—C7	120.85 (14)
N1—C1—C2—C3	1.8 (3)	C8—C7—C12—N3	2.6 (3)
C1—C2—C3—C4	−1.7 (3)	C6—C7—C12—N3	−177.08 (14)
C2—C3—C4—C5	−0.6 (2)	N3—C13—C14—C19	−175.68 (15)
C2—C3—C4—C11	−178.91 (16)	N4—C13—C14—C19	5.7 (2)
C3—C4—C5—N1	3.1 (2)	N3—C13—C14—C15	5.1 (2)
C11—C4—C5—N1	−178.52 (14)	N4—C13—C14—C15	−173.46 (15)
C3—C4—C5—C6	−175.51 (14)	C19—C14—C15—C16	−0.9 (3)
C11—C4—C5—C6	2.9 (2)	C13—C14—C15—C16	178.34 (16)
N1—C5—C6—N2	1.5 (2)	C14—C15—C16—C17	0.9 (3)
C4—C5—C6—N2	−179.89 (14)	C15—C16—C17—C18	−0.1 (3)
N1—C5—C6—C7	−176.74 (14)	C15—C16—C17—C20	179.85 (17)
C4—C5—C6—C7	1.9 (2)	C16—C17—C18—C19	−0.5 (3)
N2—C6—C7—C8	−2.1 (2)	C20—C17—C18—C19	179.49 (17)
C5—C6—C7—C8	176.11 (15)	C17—C18—C19—C14	0.5 (3)
N2—C6—C7—C12	177.60 (14)	C15—C14—C19—C18	0.3 (3)
C5—C6—C7—C12	−4.2 (2)	C13—C14—C19—C18	−178.97 (15)
C6—C7—C8—C9	1.9 (3)	C2—C1—N1—C5	0.6 (3)
C12—C7—C8—C9	−177.75 (16)	C4—C5—N1—C1	−3.0 (2)
C7—C8—C9—C10	−0.6 (3)	C6—C5—N1—C1	175.60 (15)
C8—C9—C10—N2	−0.6 (3)	C9—C10—N2—C6	0.5 (3)
C3—C4—C11—C12	172.70 (15)	C7—C6—N2—C10	0.9 (3)
C5—C4—C11—C12	−5.6 (2)	C5—C6—N2—C10	−177.34 (17)
C3—C4—C11—N4	−4.5 (3)	N4—C13—N3—C12	1.02 (17)
C5—C4—C11—N4	177.23 (15)	C14—C13—N3—C12	−177.72 (14)
N4—C11—C12—N3	0.13 (17)	C11—C12—N3—C13	−0.70 (17)
C4—C11—C12—N3	−177.65 (13)	C7—C12—N3—C13	178.22 (15)
N4—C11—C12—C7	−178.88 (13)	N3—C13—N4—C11	−0.97 (17)
C4—C11—C12—C7	3.3 (2)	C14—C13—N4—C11	177.76 (14)
C8—C7—C12—C11	−178.62 (15)	C12—C11—N4—C13	0.48 (16)
C6—C7—C12—C11	1.7 (2)	C4—C11—N4—C13	178.01 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1i	0.908 (19)	2.106 (19)	3.0131 (19)	176.0 (17)
C1—H1···N3ii	0.93	2.57	3.479 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N1i	0.908 (19)	2.106 (19)	3.0131 (19)	176.0 (17)
C1—H1⋯N3ii	0.93	2.57	3.479 (2)	165

Symmetry codes: (i) ; (ii) .