Dichloridobis(phenanthridine-κN)zinc(II).

In the mol-ecule of the title compound, [ZnCl(2)(C(13)H(9)N)(2)], the Zn(II) atom is four-coordinated in a distorted tetra-hedral configuration by two N atoms from two phenanthridine ligands and by two terminal Cl atoms. The dihedral angle between the planes of the phenanthridine ring systems is 69.92 (3)°. An intra-molecular C-H⋯Cl inter-action results in the formation of a planar five-membered ring, which is oriented at a dihedral angle of 8.32 (3)° with respect to the adjacent phenanthridine ring system. In the crystal structure, π-π contacts between the phenanthridine systems [centroid-centroid distances = 3.839 (2), 3.617 (1) and 3.682 (1) Å] may stabilize the structure. Two weak C-H⋯π inter-actions are also found.

Related literature

For related structures, see: Ahmadi et al. (2008 ▶); Çelik et al. (2004 ▶); Cui et al. (1998 ▶); Gruia et al. (2007 ▶); Khalighi et al. (2008 ▶); Khan & Tuck (1984 ▶); Khavasi et al. (2008 ▶); Kozhevnikov et al. (2006 ▶); Liu et al. (2004 ▶); Markowitz et al. (2006 ▶); Musie et al. (2004 ▶); Preston & Kennard (1969 ▶); Reimann et al. (1966 ▶); Shen et al. (2004 ▶); Steffen & Palenik (1977 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[ZnCl2(C13H9N)2]

M = 494.71

Monoclinic,

a = 16.193 (3) Å

b = 10.101 (2) Å

c = 14.491 (3) Å

β = 116.02 (3)°

V = 2130.0 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.42 mm−1

T = 298 K

0.45 × 0.30 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.610, T max = 0.740

16947 measured reflections

5732 independent reflections

4612 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.086

S = 1.09

5732 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901959X/hk2696sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901959X/hk2696Isup2.hkl

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

[ZnCl2(C13H9N)2]	F(000) = 1008
Mr = 494.71	Dx = 1.543 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1987 reflections
a = 16.193 (3) Å	θ = 2.5–29.3°
b = 10.101 (2) Å	µ = 1.42 mm−1
c = 14.491 (3) Å	T = 298 K
β = 116.02 (3)°	Prism, colorless
V = 2130.0 (9) Å3	0.45 × 0.30 × 0.22 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5732 independent reflections
Radiation source: fine-focus sealed tube	4612 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 29.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −22→22
Tmin = 0.610, Tmax = 0.740	k = −13→13
16947 measured reflections	l = −19→19

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) = 0.086	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.038P)2 + 0.5741P] where P = (Fo2 + 2Fc2)/3
5732 reflections	(Δ/σ)max = 0.013
280 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.39 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
Zn1	0.259400 (15)	0.26111 (2)	0.120119 (17)	0.03590 (7)
Cl1	0.25049 (4)	0.47913 (5)	0.09659 (5)	0.05264 (14)
Cl2	0.27473 (4)	0.19233 (6)	0.27420 (4)	0.05102 (14)
N1	0.37559 (11)	0.19993 (17)	0.10537 (13)	0.0373 (3)
N2	0.14942 (10)	0.17454 (16)	−0.00248 (12)	0.0338 (3)
C1	0.42820 (14)	0.2930 (2)	0.09724 (16)	0.0410 (4)
H1	0.4056	0.3791	0.0863	0.049*
C2	0.51762 (14)	0.2716 (2)	0.10399 (16)	0.0417 (4)
C3	0.57131 (17)	0.3780 (3)	0.09923 (19)	0.0528 (6)
H3	0.5481	0.4637	0.0902	0.063*
C4	0.65812 (18)	0.3558 (3)	0.1079 (2)	0.0626 (7)
H4	0.6936	0.4260	0.1039	0.075*
C5	0.69249 (18)	0.2273 (3)	0.1228 (2)	0.0674 (8)
H5	0.7512	0.2124	0.1283	0.081*
C6	0.64215 (16)	0.1227 (3)	0.1293 (2)	0.0574 (6)
H6	0.6672	0.0380	0.1401	0.069*
C7	0.55249 (14)	0.1417 (2)	0.11974 (15)	0.0432 (5)
C8	0.49487 (14)	0.0368 (2)	0.12662 (15)	0.0409 (4)
C9	0.52121 (17)	−0.0978 (2)	0.13981 (17)	0.0503 (5)
H9	0.5782	−0.1218	0.1441	0.060*
C10	0.46418 (19)	−0.1931 (2)	0.14633 (18)	0.0548 (6)
H10	0.4828	−0.2812	0.1547	0.066*
C11	0.37861 (18)	−0.1601 (2)	0.14065 (18)	0.0517 (5)
H11	0.3404	−0.2259	0.1453	0.062*
C12	0.35073 (16)	−0.0305 (2)	0.12812 (16)	0.0448 (5)
H12	0.2939	−0.0084	0.1251	0.054*
C13	0.40733 (14)	0.0686 (2)	0.11980 (14)	0.0377 (4)
C14	0.16296 (13)	0.12723 (19)	−0.07864 (15)	0.0360 (4)
H14	0.2222	0.1316	−0.0736	0.043*
C15	0.09352 (13)	0.06958 (18)	−0.16859 (14)	0.0348 (4)
C16	0.11488 (16)	0.0160 (2)	−0.24580 (16)	0.0417 (4)
H16	0.1747	0.0203	−0.2389	0.050*
C17	0.04765 (18)	−0.0419 (2)	−0.33016 (18)	0.0486 (5)
H17	0.0615	−0.0771	−0.3810	0.058*
C18	−0.04216 (17)	−0.0482 (2)	−0.34024 (18)	0.0510 (5)
H18	−0.0876	−0.0881	−0.3981	0.061*
C19	−0.06479 (15)	0.0033 (2)	−0.26642 (17)	0.0454 (5)
H19	−0.1250	−0.0022	−0.2746	0.054*
C20	0.00307 (13)	0.06448 (18)	−0.17833 (14)	0.0343 (4)
C21	−0.01463 (13)	0.12123 (18)	−0.09734 (15)	0.0343 (4)
C22	−0.10280 (14)	0.1282 (2)	−0.10056 (17)	0.0430 (5)
H22	−0.1531	0.0952	−0.1574	0.052*
C23	−0.11556 (15)	0.1830 (2)	−0.02101 (19)	0.0481 (5)
H23	−0.1743	0.1872	−0.0247	0.058*
C24	−0.04179 (17)	0.2319 (2)	0.06441 (19)	0.0476 (5)
H24	−0.0510	0.2678	0.1183	0.057*
C25	0.04526 (15)	0.2277 (2)	0.07015 (17)	0.0417 (4)
H25	0.0947	0.2608	0.1279	0.050*
C26	0.05989 (12)	0.17376 (18)	−0.01046 (14)	0.0328 (4)

	U11	U22	U33	U12	U13	U23
Zn1	0.02853 (11)	0.03705 (12)	0.03880 (12)	−0.00174 (9)	0.01173 (8)	−0.00362 (9)
Cl1	0.0510 (3)	0.0376 (3)	0.0687 (4)	0.0014 (2)	0.0258 (3)	−0.0007 (2)
Cl2	0.0481 (3)	0.0596 (3)	0.0436 (3)	−0.0047 (3)	0.0185 (2)	0.0027 (2)
N1	0.0312 (8)	0.0388 (8)	0.0385 (8)	0.0034 (7)	0.0120 (7)	−0.0012 (7)
N2	0.0265 (7)	0.0339 (7)	0.0374 (8)	−0.0007 (6)	0.0107 (6)	−0.0010 (6)
C1	0.0341 (10)	0.0424 (10)	0.0442 (11)	0.0019 (8)	0.0149 (8)	−0.0014 (8)
C2	0.0317 (9)	0.0543 (12)	0.0367 (10)	−0.0003 (9)	0.0127 (8)	−0.0022 (9)
C3	0.0439 (12)	0.0640 (15)	0.0506 (13)	−0.0062 (11)	0.0207 (10)	−0.0017 (11)
C4	0.0429 (13)	0.087 (2)	0.0608 (15)	−0.0129 (13)	0.0250 (12)	−0.0031 (14)
C5	0.0333 (11)	0.104 (2)	0.0666 (16)	0.0047 (14)	0.0232 (11)	−0.0006 (15)
C6	0.0354 (11)	0.0780 (17)	0.0564 (14)	0.0117 (12)	0.0178 (10)	0.0020 (12)
C7	0.0311 (9)	0.0620 (13)	0.0325 (10)	0.0082 (9)	0.0103 (8)	−0.0010 (9)
C8	0.0339 (9)	0.0511 (11)	0.0306 (9)	0.0092 (9)	0.0075 (7)	−0.0005 (8)
C9	0.0453 (12)	0.0557 (13)	0.0419 (11)	0.0201 (11)	0.0116 (10)	0.0029 (10)
C10	0.0656 (16)	0.0453 (12)	0.0409 (11)	0.0180 (12)	0.0116 (11)	0.0035 (9)
C11	0.0556 (14)	0.0425 (11)	0.0462 (12)	−0.0001 (10)	0.0123 (10)	0.0037 (9)
C12	0.0395 (11)	0.0457 (11)	0.0430 (11)	0.0007 (9)	0.0125 (9)	−0.0004 (9)
C13	0.0329 (9)	0.0412 (10)	0.0317 (9)	0.0044 (8)	0.0074 (7)	−0.0023 (8)
C14	0.0286 (9)	0.0373 (9)	0.0394 (10)	−0.0009 (7)	0.0125 (8)	0.0010 (8)
C15	0.0346 (9)	0.0313 (9)	0.0351 (9)	−0.0016 (7)	0.0121 (8)	0.0008 (7)
C16	0.0436 (11)	0.0391 (10)	0.0431 (11)	0.0040 (9)	0.0198 (9)	0.0000 (8)
C17	0.0593 (14)	0.0412 (11)	0.0448 (12)	−0.0011 (10)	0.0223 (11)	−0.0077 (9)
C18	0.0519 (13)	0.0433 (11)	0.0459 (12)	−0.0085 (10)	0.0105 (10)	−0.0100 (9)
C19	0.0383 (10)	0.0408 (10)	0.0488 (12)	−0.0094 (9)	0.0116 (9)	−0.0039 (9)
C20	0.0313 (9)	0.0286 (8)	0.0375 (9)	−0.0026 (7)	0.0099 (7)	0.0025 (7)
C21	0.0306 (9)	0.0295 (8)	0.0405 (10)	−0.0020 (7)	0.0133 (8)	0.0036 (7)
C22	0.0307 (9)	0.0444 (11)	0.0513 (12)	−0.0046 (8)	0.0155 (9)	−0.0001 (9)
C23	0.0359 (10)	0.0465 (11)	0.0676 (15)	0.0004 (9)	0.0278 (10)	0.0024 (10)
C24	0.0468 (12)	0.0447 (11)	0.0588 (13)	0.0003 (10)	0.0302 (11)	−0.0060 (10)
C25	0.0378 (10)	0.0409 (10)	0.0455 (11)	−0.0024 (8)	0.0175 (9)	−0.0062 (8)
C26	0.0287 (8)	0.0290 (8)	0.0394 (9)	−0.0012 (7)	0.0138 (7)	0.0014 (7)

Cl1—Zn1	2.2234 (7)	C12—H12	0.9300
Cl2—Zn1	2.2456 (7)	C13—N1	1.405 (3)
N1—Zn1	2.0785 (17)	C14—N2	1.306 (2)
N2—Zn1	2.0775 (17)	C14—C15	1.420 (3)
C1—N1	1.308 (3)	C14—H14	0.9300
C1—C2	1.424 (3)	C15—C20	1.410 (3)
C1—H1	0.9300	C15—C16	1.416 (3)
C2—C3	1.402 (3)	C16—C17	1.361 (3)
C2—C7	1.407 (3)	C16—H16	0.9300
C3—C4	1.374 (4)	C17—C18	1.398 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.392 (4)	C18—C19	1.376 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.363 (4)	C19—C20	1.410 (3)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.410 (3)	C20—C21	1.443 (3)
C6—H6	0.9300	C21—C22	1.410 (3)
C7—C8	1.444 (3)	C21—C26	1.411 (3)
C8—C9	1.412 (3)	C22—C23	1.374 (3)
C8—C13	1.414 (3)	C22—H22	0.9300
C9—C10	1.366 (4)	C23—C24	1.380 (3)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.392 (4)	C24—C25	1.376 (3)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.371 (3)	C25—C26	1.400 (3)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.398 (3)	C26—N2	1.403 (2)
N2—Zn1—N1	105.19 (7)	C11—C12—C13	120.3 (2)
N2—Zn1—Cl1	108.18 (5)	C11—C12—H12	119.8
N1—Zn1—Cl1	106.23 (5)	C13—C12—H12	119.8
N2—Zn1—Cl2	113.54 (5)	C12—C13—N1	118.57 (18)
N1—Zn1—Cl2	107.46 (6)	C12—C13—C8	120.43 (19)
Cl1—Zn1—Cl2	115.49 (3)	N1—C13—C8	121.00 (19)
C1—N1—C13	118.80 (18)	N2—C14—C15	124.52 (18)
C1—N1—Zn1	116.76 (14)	N2—C14—H14	117.7
C13—N1—Zn1	123.65 (14)	C15—C14—H14	117.7
C14—N2—C26	118.60 (16)	C20—C15—C16	120.69 (18)
C14—N2—Zn1	118.54 (13)	C20—C15—C14	118.46 (18)
C26—N2—Zn1	122.69 (13)	C16—C15—C14	120.84 (19)
N1—C1—C2	124.6 (2)	C17—C16—C15	119.8 (2)
N1—C1—H1	117.7	C17—C16—H16	120.1
C2—C1—H1	117.7	C15—C16—H16	120.1
C3—C2—C7	120.6 (2)	C16—C17—C18	119.9 (2)
C3—C2—C1	120.9 (2)	C16—C17—H17	120.0
C7—C2—C1	118.4 (2)	C18—C17—H17	120.0
C4—C3—C2	120.2 (3)	C19—C18—C17	121.4 (2)
C4—C3—H3	119.9	C19—C18—H18	119.3
C2—C3—H3	119.9	C17—C18—H18	119.3
C3—C4—C5	119.3 (3)	C18—C19—C20	120.1 (2)
C3—C4—H4	120.3	C18—C19—H19	119.9
C5—C4—H4	120.3	C20—C19—H19	119.9
C6—C5—C4	121.5 (2)	C15—C20—C19	118.01 (19)
C6—C5—H5	119.2	C15—C20—C21	118.19 (17)
C4—C5—H5	119.2	C19—C20—C21	123.80 (18)
C5—C6—C7	120.6 (3)	C22—C21—C26	117.92 (18)
C5—C6—H6	119.7	C22—C21—C20	123.54 (18)
C7—C6—H6	119.7	C26—C21—C20	118.54 (17)
C2—C7—C6	117.8 (2)	C23—C22—C21	121.0 (2)
C2—C7—C8	118.03 (19)	C23—C22—H22	119.5
C6—C7—C8	124.2 (2)	C21—C22—H22	119.5
C9—C8—C13	117.5 (2)	C22—C23—C24	120.5 (2)
C9—C8—C7	123.3 (2)	C22—C23—H23	119.8
C13—C8—C7	119.14 (19)	C24—C23—H23	119.8
C10—C9—C8	121.0 (2)	C25—C24—C23	120.2 (2)
C10—C9—H9	119.5	C25—C24—H24	119.9
C8—C9—H9	119.5	C23—C24—H24	119.9
C9—C10—C11	120.9 (2)	C24—C25—C26	120.4 (2)
C9—C10—H10	119.6	C24—C25—H25	119.8
C11—C10—H10	119.6	C26—C25—H25	119.8
C12—C11—C10	119.8 (2)	C25—C26—N2	118.43 (17)
C12—C11—H11	120.1	C25—C26—C21	119.96 (18)
C10—C11—H11	120.1	N2—C26—C21	121.61 (17)
N1—C1—C2—C3	−177.0 (2)	C18—C19—C20—C21	179.9 (2)
N1—C1—C2—C7	0.5 (3)	C15—C20—C21—C22	176.71 (18)
C7—C2—C3—C4	1.3 (3)	C19—C20—C21—C22	−3.7 (3)
C1—C2—C3—C4	178.7 (2)	C15—C20—C21—C26	−2.7 (3)
C2—C3—C4—C5	−0.8 (4)	C19—C20—C21—C26	176.82 (19)
C3—C4—C5—C6	−0.2 (4)	C26—C21—C22—C23	−0.8 (3)
C4—C5—C6—C7	0.8 (4)	C20—C21—C22—C23	179.8 (2)
C3—C2—C7—C6	−0.7 (3)	C21—C22—C23—C24	−0.4 (3)
C1—C2—C7—C6	−178.2 (2)	C22—C23—C24—C25	0.8 (4)
C3—C2—C7—C8	178.41 (19)	C23—C24—C25—C26	0.0 (3)
C1—C2—C7—C8	0.9 (3)	C24—C25—C26—N2	178.40 (19)
C5—C6—C7—C2	−0.4 (4)	C24—C25—C26—C21	−1.2 (3)
C5—C6—C7—C8	−179.4 (2)	C22—C21—C26—C25	1.5 (3)
C2—C7—C8—C9	178.4 (2)	C20—C21—C26—C25	−179.01 (17)
C6—C7—C8—C9	−2.5 (3)	C22—C21—C26—N2	−178.02 (17)
C2—C7—C8—C13	−1.5 (3)	C20—C21—C26—N2	1.4 (3)
C6—C7—C8—C13	177.6 (2)	C2—C1—N1—C13	−1.3 (3)
C13—C8—C9—C10	−0.4 (3)	C2—C1—N1—Zn1	168.86 (16)
C7—C8—C9—C10	179.7 (2)	C12—C13—N1—C1	−179.80 (18)
C8—C9—C10—C11	−0.3 (4)	C8—C13—N1—C1	0.7 (3)
C9—C10—C11—C12	0.2 (4)	C12—C13—N1—Zn1	10.7 (2)
C10—C11—C12—C13	0.8 (3)	C8—C13—N1—Zn1	−168.77 (14)
C11—C12—C13—N1	179.0 (2)	C15—C14—N2—C26	−2.6 (3)
C11—C12—C13—C8	−1.5 (3)	C15—C14—N2—Zn1	−177.82 (14)
C9—C8—C13—C12	1.3 (3)	C25—C26—N2—C14	−178.37 (18)
C7—C8—C13—C12	−178.80 (18)	C21—C26—N2—C14	1.2 (3)
C9—C8—C13—N1	−179.20 (18)	C25—C26—N2—Zn1	−3.3 (2)
C7—C8—C13—N1	0.7 (3)	C21—C26—N2—Zn1	176.23 (13)
N2—C14—C15—C20	1.2 (3)	C14—N2—Zn1—N1	−15.81 (16)
N2—C14—C15—C16	−177.53 (18)	C26—N2—Zn1—N1	169.13 (14)
C20—C15—C16—C17	−0.4 (3)	C14—N2—Zn1—Cl1	97.39 (14)
C14—C15—C16—C17	178.30 (19)	C26—N2—Zn1—Cl1	−77.67 (14)
C15—C16—C17—C18	0.0 (3)	C14—N2—Zn1—Cl2	−133.03 (13)
C16—C17—C18—C19	0.2 (4)	C26—N2—Zn1—Cl2	51.91 (15)
C17—C18—C19—C20	0.1 (3)	C1—N1—Zn1—N2	121.89 (15)
C16—C15—C20—C19	0.7 (3)	C13—N1—Zn1—N2	−68.46 (16)
C14—C15—C20—C19	−178.05 (18)	C1—N1—Zn1—Cl1	7.32 (16)
C16—C15—C20—C21	−179.75 (17)	C13—N1—Zn1—Cl1	176.97 (14)
C14—C15—C20—C21	1.5 (3)	C1—N1—Zn1—Cl2	−116.83 (14)
C18—C19—C20—C15	−0.6 (3)	C13—N1—Zn1—Cl2	52.82 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.93	2.77	3.434 (3)	129
C17—H17···Cg6i	0.93	2.82	3.535 (3)	134
C24—H24···Cg5ii	0.93	2.81	3.508 (3)	132

Cl1—Zn1	2.2234 (7)
Cl2—Zn1	2.2456 (7)
N1—Zn1	2.0785 (17)
N2—Zn1	2.0775 (17)

N2—Zn1—N1	105.19 (7)
N2—Zn1—Cl1	108.18 (5)
N1—Zn1—Cl1	106.23 (5)
N2—Zn1—Cl2	113.54 (5)
N1—Zn1—Cl2	107.46 (6)
Cl1—Zn1—Cl2	115.49 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl1	0.93	2.77	3.434 (3)	129
C17—H17⋯Cg6i	0.93	2.82	3.535 (3)	134
C24—H24⋯Cg5ii	0.93	2.81	3.508 (3)	132

Symmetry codes: (i) ; (ii) . Cg5 and Cg6 are the centroids of the C15–C20 and C21–C26 rings, respectively.