3-Phenyl-1-[2-(3-phenyl-isoquinolin-1-yl)-diselan-yl]isoquinoline.

The complete molecule of the title compound, C(30)H(20)N(2)Se(2), is generated by a crystallographic inversion centre at the mid-point of the Se-Se bond. The dihedral angle between the isoquinoline-1-selenol group and the phenyl ring is 14.92 (2)°. The herringbone-like packing of the structure is supported by inter-molecular π-π stacking inter-actions with a shortest perpendicular distance between isoquinoline groups of 3.514 Å; the slippage between these ring systems is 0.972 Å, and the distance between the centroids of the six-membered carbon rings is 3.645 (3) Å.

Related literature

For biological properties of organoselenium compounds, see: Mugesh & Singh (2000 ▶). For chemopreventive agents in human cancer therapy, see: Sugie et al. (2000 ▶).

Experimental

Crystal data

C30H20N2Se2

M = 566.40

Monoclinic,

a = 11.2441 (17) Å

b = 17.559 (3) Å

c = 13.248 (3) Å

β = 115.082 (2)°

V = 2369.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 3.14 mm−1

T = 290 (2) K

0.20 × 0.14 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.585, T max = 0.703

8668 measured reflections

2207 independent reflections

1516 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.102

S = 1.00

2207 reflections

158 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803609X/si2124sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803609X/si2124Isup2.hkl

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

C30H20N2Se2	F000 = 1128
Mr = 566.40	Dx = 1.588 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 948 reflections
a = 11.2441 (17) Å	θ = 2.3–24.6º
b = 17.559 (3) Å	µ = 3.14 mm−1
c = 13.248 (3) Å	T = 290 (2) K
β = 115.082 (2)º	Block, brown
V = 2369.0 (8) Å3	0.20 × 0.14 × 0.11 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2207 independent reflections
Radiation source: fine-focus sealed tube	1516 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
T = 290(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.585, Tmax = 0.703	k = −21→19
8668 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0594P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2207 reflections	Δρmax = 0.66 e Å−3
158 parameters	Δρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Se1	0.85678 (4)	0.23078 (2)	1.05937 (3)	0.0658 (2)
N1	0.8556 (3)	0.35522 (16)	0.9293 (2)	0.0532 (7)
C1	0.9346 (4)	0.3092 (2)	1.0051 (3)	0.0546 (9)
C2	0.9077 (3)	0.41108 (19)	0.8880 (3)	0.0509 (9)
C3	1.0405 (4)	0.4174 (2)	0.9231 (3)	0.0590 (10)
H3	1.0741	0.4550	0.8929	0.071*
C4	1.2651 (4)	0.3718 (3)	1.0436 (3)	0.0732 (12)
H4	1.3018	0.4088	1.0153	0.088*
C5	1.3442 (4)	0.3224 (3)	1.1219 (4)	0.0837 (13)
H5	1.4347	0.3251	1.1456	0.100*
C6	1.2919 (5)	0.2680 (3)	1.1666 (4)	0.0815 (13)
H6	1.3474	0.2354	1.2218	0.098*
C7	1.1602 (5)	0.2619 (2)	1.1307 (3)	0.0745 (12)
H7	1.1262	0.2243	1.1603	0.089*
C8	1.0740 (4)	0.3116 (2)	1.0490 (3)	0.0556 (9)
C9	1.1271 (4)	0.3676 (2)	1.0047 (3)	0.0562 (9)
C10	0.8121 (4)	0.4607 (2)	0.8015 (3)	0.0523 (9)
C11	0.8492 (4)	0.5283 (2)	0.7693 (3)	0.0617 (10)
H11	0.9360	0.5443	0.8056	0.074*
C12	0.7610 (4)	0.5723 (2)	0.6852 (3)	0.0729 (12)
H12	0.7884	0.6172	0.6644	0.088*
C13	0.6320 (4)	0.5498 (3)	0.6320 (3)	0.0755 (12)
H13	0.5724	0.5788	0.5738	0.091*
C14	0.5918 (5)	0.4853 (3)	0.6642 (4)	0.0812 (13)
H14	0.5039	0.4711	0.6297	0.097*
C15	0.6803 (4)	0.4402 (2)	0.7479 (3)	0.0678 (10)
H15	0.6515	0.3958	0.7686	0.081*

	U11	U22	U33	U12	U13	U23
Se1	0.0824 (3)	0.0453 (3)	0.0779 (3)	−0.0142 (2)	0.0420 (2)	0.00255 (19)
N1	0.0679 (19)	0.0398 (17)	0.0617 (18)	−0.0123 (15)	0.0370 (16)	−0.0059 (15)
C1	0.071 (3)	0.041 (2)	0.060 (2)	−0.0144 (19)	0.036 (2)	−0.0107 (19)
C2	0.066 (2)	0.040 (2)	0.058 (2)	−0.0114 (17)	0.0373 (18)	−0.0113 (17)
C3	0.073 (3)	0.055 (2)	0.059 (2)	−0.0138 (19)	0.038 (2)	−0.0005 (19)
C4	0.068 (3)	0.085 (3)	0.066 (3)	−0.014 (2)	0.028 (2)	0.003 (2)
C5	0.070 (3)	0.107 (4)	0.068 (3)	−0.009 (3)	0.023 (2)	−0.003 (3)
C6	0.084 (3)	0.083 (3)	0.064 (3)	0.000 (3)	0.018 (2)	0.004 (2)
C7	0.089 (3)	0.063 (3)	0.073 (3)	−0.011 (2)	0.036 (3)	0.002 (2)
C8	0.074 (3)	0.047 (2)	0.053 (2)	−0.0104 (19)	0.033 (2)	−0.0098 (18)
C9	0.067 (2)	0.056 (2)	0.051 (2)	−0.0148 (19)	0.0311 (19)	−0.0088 (18)
C10	0.069 (2)	0.044 (2)	0.057 (2)	−0.0042 (18)	0.040 (2)	−0.0073 (17)
C11	0.074 (3)	0.052 (2)	0.076 (3)	−0.0048 (19)	0.048 (2)	−0.003 (2)
C12	0.099 (3)	0.055 (3)	0.084 (3)	0.007 (2)	0.058 (3)	0.012 (2)
C13	0.083 (3)	0.079 (3)	0.069 (3)	0.015 (3)	0.036 (3)	0.005 (2)
C14	0.077 (3)	0.087 (4)	0.074 (3)	−0.007 (3)	0.027 (2)	−0.001 (3)
C15	0.073 (3)	0.059 (3)	0.074 (3)	−0.012 (2)	0.034 (2)	−0.006 (2)

Se1—C1	1.928 (4)	C6—H6	0.9300
Se1—Se1i	2.3439 (9)	C7—C8	1.408 (5)
N1—C1	1.301 (4)	C7—H7	0.9300
N1—C2	1.370 (4)	C8—C9	1.402 (5)
C1—C8	1.422 (5)	C10—C11	1.383 (5)
C2—C3	1.368 (5)	C10—C15	1.392 (5)
C2—C10	1.478 (5)	C11—C12	1.373 (5)
C3—C9	1.410 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.375 (5)
C4—C5	1.356 (6)	C12—H12	0.9300
C4—C9	1.415 (5)	C13—C14	1.354 (6)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.380 (6)	C14—C15	1.381 (5)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.354 (6)	C15—H15	0.9300
C1—Se1—Se1i	92.40 (12)	C9—C8—C1	116.1 (3)
C1—N1—C2	119.0 (3)	C7—C8—C1	125.2 (4)
N1—C1—C8	124.9 (3)	C8—C9—C3	118.6 (3)
N1—C1—Se1	117.5 (3)	C8—C9—C4	118.7 (4)
C8—C1—Se1	117.6 (3)	C3—C9—C4	122.7 (4)
C3—C2—N1	120.8 (3)	C11—C10—C15	117.3 (4)
C3—C2—C10	123.1 (3)	C11—C10—C2	122.0 (3)
N1—C2—C10	116.0 (3)	C15—C10—C2	120.7 (3)
C2—C3—C9	120.6 (3)	C12—C11—C10	121.6 (4)
C2—C3—H3	119.7	C12—C11—H11	119.2
C9—C3—H3	119.7	C10—C11—H11	119.2
C5—C4—C9	120.5 (4)	C11—C12—C13	119.8 (4)
C5—C4—H4	119.7	C11—C12—H12	120.1
C9—C4—H4	119.7	C13—C12—H12	120.1
C4—C5—C6	120.7 (4)	C14—C13—C12	120.0 (4)
C4—C5—H5	119.7	C14—C13—H13	120.0
C6—C5—H5	119.7	C12—C13—H13	120.0
C7—C6—C5	120.4 (4)	C13—C14—C15	120.6 (4)
C7—C6—H6	119.8	C13—C14—H14	119.7
C5—C6—H6	119.8	C15—C14—H14	119.7
C6—C7—C8	121.0 (4)	C14—C15—C10	120.7 (4)
C6—C7—H7	119.5	C14—C15—H15	119.7
C8—C7—H7	119.5	C10—C15—H15	119.7
C9—C8—C7	118.7 (4)
C2—N1—C1—C8	−0.6 (5)	C7—C8—C9—C4	0.1 (5)
C2—N1—C1—Se1	−179.3 (2)	C1—C8—C9—C4	−178.8 (3)
Se1i—Se1—C1—N1	0.9 (3)	C2—C3—C9—C8	−0.1 (5)
Se1i—Se1—C1—C8	−177.9 (3)	C2—C3—C9—C4	179.9 (3)
C1—N1—C2—C3	1.8 (5)	C5—C4—C9—C8	0.3 (6)
C1—N1—C2—C10	179.4 (3)	C5—C4—C9—C3	−179.7 (4)
N1—C2—C3—C9	−1.5 (5)	C3—C2—C10—C11	−16.2 (5)
C10—C2—C3—C9	−178.9 (3)	N1—C2—C10—C11	166.3 (3)
C9—C4—C5—C6	−1.3 (7)	C3—C2—C10—C15	163.0 (3)
C4—C5—C6—C7	1.9 (7)	N1—C2—C10—C15	−14.5 (5)
C5—C6—C7—C8	−1.5 (7)	C15—C10—C11—C12	−2.3 (5)
C6—C7—C8—C9	0.4 (6)	C2—C10—C11—C12	176.9 (3)
C6—C7—C8—C1	179.2 (4)	C10—C11—C12—C13	0.9 (6)
N1—C1—C8—C9	−0.9 (5)	C11—C12—C13—C14	1.5 (6)
Se1—C1—C8—C9	177.8 (2)	C12—C13—C14—C15	−2.2 (7)
N1—C1—C8—C7	−179.7 (3)	C13—C14—C15—C10	0.7 (6)
Se1—C1—C8—C7	−1.1 (5)	C11—C10—C15—C14	1.6 (6)
C7—C8—C9—C3	−179.9 (3)	C2—C10—C15—C14	−177.7 (3)
C1—C8—C9—C3	1.2 (5)