11H-Dibenzo[b,e]azepine-6-carbonitrile

Fan, G.-D.; Xiao, Y.-L.; You, G.-R.; Duan, G.-Y.

doi:10.1107/S1600536808033072

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2126

doi:10.1107/S1600536808033072

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11H-Dibenzo[b,e]azepine-6-carbonitrile

Guo-Dong Fan,^a Yu-Liang Xiao,^b Gui-Rong You ^b and Gui-Yun Duan ^b ^*

^aCollege of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, People's Republic of China, and ^bCollege of Pharmaceutical Sciences, Taishan Medical College, Tai'an 271016, People's Republic of China
^*Correspondence e-mail: duanguiyun@yahoo.cn

(Received 5 October 2008; accepted 13 October 2008; online 18 October 2008)

The title compound, C₁₅H₁₀N₂, crystallizes with two independent molecules in the asymmetric unit. The two benzene rings make dihedral angles of 60.32 (2) and 61.35 (3)°. The crystal packing is stabilized by weak π–π stacking interactions [centroid-to-centroid distances = 3.673 (4) and 3.793 (4) Å].

Related literature

For discussions of the biological activity of the title compound, see: Bakker et al. (2000 ); Bielory & Ghafoor (2005 ); Schmutz et al. (1967 ). For a similar structure, see: Li et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₀N₂
M_r = 218.25
Triclinic, $[P \overline 1]$
a = 10.125 (2) Å
b = 10.275 (2) Å
c = 12.749 (3) Å
α = 105.96 (3)°
β = 99.18 (2)°
γ = 109.04 (3)°
V = 1159.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 (2) K
0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.989, T_max = 0.993
12026 measured reflections
4084 independent reflections
3382 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.097
S = 1.03
4084 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Selected interatomic distances (Å)

Cg1 is the centroid of the ring C8–C13 and Cg2 is the centroid of the ring C23–C28.

Cg1⋯Cg1ⁱ	3.673 (4)
Cg2⋯Cg2ⁱⁱ	3.793 (4)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033072/sg2271sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033072/sg2271Isup2.hkl

checkCIF report

Comment top

The title compound, (1), is an intermediate in the synthesis of Epinastine which is an antihistamine agent (Bakker et al., 2000; Bielory & Ghafoor, 2005), and was first synthesized in 1967 (Schmutz et al., 1967).

Compound (1) crystallizes with two independent molecules in the asymmetric unit (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Li et al., 2006). The dihedral angles between the planes of benzene rings in the two independent molecules are 60.32 (2) and 61.35 (3)°. π–π stacking interactions (Table 1) are present in the structure (Cg1: C8–C13; Cg2: C23–C28).

Related literature top

For discussions of the biological activity of the title compound, see: Bakker et al. (2000); Bielory & Ghafoor (2005); Schmutz et al. (1967). For a similar structure, see: Li et al. (2006).

Experimental top

Compound (1) was synthesized from 6-chlor-11H-dibenzo[b,e]azepine (1 mmol, 0.23 g) and sodium cyanade (1.1 mmol, 0.05 g) in 10 ml DMSO as solvent at 363 K for 5 h to afford the title compound (Yield 73%, 0.16 g). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a methanol solution at room temperature for one week.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound (I), with displacement ellipsoids drawn at the 35% probability level.

11H-Dibenzo[b,e]azepine-6-carbonitrile top

Crystal data top

C₁₅H₁₀N₂	Z = 4
M_r = 218.25	F(000) = 456
Triclinic, P1	D_x = 1.251 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.125 (2) Å	Cell parameters from 4851 reflections
b = 10.275 (2) Å	θ = 2.2–28.0°
c = 12.749 (3) Å	µ = 0.08 mm⁻¹
α = 105.96 (3)°	T = 273 K
β = 99.18 (2)°	Block, brown
γ = 109.04 (3)°	0.15 × 0.12 × 0.10 mm
V = 1159.2 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4084 independent reflections
Radiation source: fine-focus sealed tube	3382 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.989, T_max = 0.993	k = −12→12
12026 measured reflections	l = −14→15

Refinement top

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0446P)² + 0.1613P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4084 reflections	Δρ_max = 0.19 e Å⁻³
308 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.037 (2)

Crystal data top

C₁₅H₁₀N₂	γ = 109.04 (3)°
M_r = 218.25	V = 1159.2 (6) Å³
Triclinic, P1	Z = 4
a = 10.125 (2) Å	Mo Kα radiation
b = 10.275 (2) Å	µ = 0.08 mm⁻¹
c = 12.749 (3) Å	T = 273 K
α = 105.96 (3)°	0.15 × 0.12 × 0.10 mm
β = 99.18 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4084 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3382 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.993	R_int = 0.021
12026 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
4084 reflections	Δρ_min = −0.13 e Å⁻³
308 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.93668 (11)	0.20617 (11)	0.18911 (9)	0.0486 (3)
N2	1.10390 (18)	0.47578 (17)	0.10411 (14)	0.0874 (4)
N3	0.33399 (10)	0.33411 (11)	0.30617 (9)	0.0474 (3)
N4	0.42697 (16)	0.69062 (15)	0.35893 (13)	0.0816 (4)
C1	0.87147 (12)	0.11423 (13)	0.24622 (10)	0.0466 (3)
C2	0.93247 (14)	0.01429 (14)	0.25883 (12)	0.0568 (3)
H2A	1.0096	0.0105	0.2288	0.068*
C3	0.87991 (17)	−0.07883 (16)	0.31523 (14)	0.0699 (4)
H3B	0.9238	−0.1425	0.3261	0.084*
C4	0.76259 (18)	−0.07763 (18)	0.35547 (14)	0.0747 (5)
H4A	0.7275	−0.1399	0.3944	0.090*
C5	0.69679 (16)	0.01499 (17)	0.33859 (13)	0.0679 (4)
H5A	0.6151	0.0122	0.3640	0.082*
C6	0.74956 (13)	0.11314 (15)	0.28418 (11)	0.0532 (3)
C7	0.67936 (14)	0.21544 (17)	0.26432 (13)	0.0644 (4)
H7A	0.6553	0.2013	0.1841	0.077*
H7B	0.5900	0.1936	0.2871	0.077*
C8	0.78013 (14)	0.37191 (16)	0.33094 (11)	0.0549 (3)
C9	0.74955 (18)	0.4600 (2)	0.41954 (13)	0.0707 (4)
H9A	0.6653	0.4210	0.4403	0.085*
C10	0.8421 (2)	0.6044 (2)	0.47717 (14)	0.0800 (5)
H10A	0.8204	0.6615	0.5369	0.096*
C11	0.9659 (2)	0.66483 (19)	0.44740 (13)	0.0732 (4)
H11A	1.0271	0.7630	0.4859	0.088*
C12	0.99953 (16)	0.58006 (15)	0.36048 (12)	0.0596 (4)
H12A	1.0832	0.6213	0.3398	0.071*
C13	0.90890 (13)	0.43261 (14)	0.30305 (10)	0.0486 (3)
C14	0.95118 (13)	0.34087 (14)	0.21488 (10)	0.0469 (3)
C15	1.03427 (15)	0.41783 (15)	0.14911 (12)	0.0549 (3)
C16	0.30864 (12)	0.18357 (13)	0.26934 (11)	0.0457 (3)
C17	0.32200 (14)	0.12481 (16)	0.35496 (12)	0.0570 (3)
H17A	0.3485	0.1854	0.4305	0.068*
C18	0.29646 (18)	−0.02147 (18)	0.32903 (16)	0.0717 (4)
H18A	0.3087	−0.0591	0.3867	0.086*
C19	0.2528 (2)	−0.11204 (18)	0.21765 (17)	0.0804 (5)
H19A	0.2344	−0.2115	0.1997	0.097*
C20	0.23630 (18)	−0.05569 (16)	0.13243 (15)	0.0703 (4)
H20A	0.2060	−0.1184	0.0573	0.084*
C21	0.26371 (13)	0.09205 (14)	0.15582 (11)	0.0508 (3)
C22	0.24469 (15)	0.15472 (15)	0.06392 (11)	0.0577 (4)
H22A	0.1773	0.2029	0.0739	0.069*
H22B	0.2046	0.0762	−0.0095	0.069*
C23	0.38852 (15)	0.26340 (15)	0.06805 (11)	0.0518 (3)
C24	0.45555 (19)	0.23862 (18)	−0.01782 (13)	0.0684 (4)
H24A	0.4114	0.1515	−0.0800	0.082*
C25	0.5865 (2)	0.3412 (2)	−0.01221 (15)	0.0777 (5)
H25A	0.6302	0.3222	−0.0704	0.093*
C26	0.65358 (17)	0.4714 (2)	0.07818 (15)	0.0715 (4)
H26A	0.7420	0.5402	0.0811	0.086*
C27	0.58889 (15)	0.49905 (16)	0.16430 (13)	0.0583 (4)
H27A	0.6326	0.5879	0.2249	0.070*
C28	0.45808 (13)	0.39437 (14)	0.16093 (11)	0.0467 (3)
C29	0.39603 (13)	0.42144 (13)	0.25784 (10)	0.0459 (3)
C30	0.41483 (15)	0.57366 (16)	0.31439 (12)	0.0566 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0475 (6)	0.0505 (6)	0.0503 (6)	0.0185 (5)	0.0175 (5)	0.0198 (5)
N2	0.0998 (11)	0.0880 (10)	0.0966 (11)	0.0383 (9)	0.0484 (9)	0.0511 (9)
N3	0.0454 (5)	0.0503 (6)	0.0456 (6)	0.0166 (5)	0.0171 (5)	0.0152 (5)
N4	0.0931 (10)	0.0557 (8)	0.0875 (10)	0.0253 (7)	0.0296 (8)	0.0140 (7)
C1	0.0414 (6)	0.0468 (7)	0.0461 (7)	0.0105 (5)	0.0116 (5)	0.0163 (6)
C2	0.0511 (7)	0.0501 (8)	0.0691 (9)	0.0171 (6)	0.0189 (6)	0.0229 (7)
C3	0.0716 (9)	0.0565 (9)	0.0850 (11)	0.0206 (7)	0.0198 (8)	0.0363 (8)
C4	0.0769 (10)	0.0655 (10)	0.0781 (11)	0.0102 (8)	0.0259 (9)	0.0385 (9)
C5	0.0525 (8)	0.0725 (10)	0.0725 (10)	0.0095 (7)	0.0263 (7)	0.0289 (8)
C6	0.0393 (6)	0.0592 (8)	0.0535 (8)	0.0112 (6)	0.0119 (6)	0.0184 (6)
C7	0.0404 (7)	0.0874 (11)	0.0719 (10)	0.0274 (7)	0.0195 (7)	0.0325 (8)
C8	0.0533 (7)	0.0761 (9)	0.0526 (8)	0.0391 (7)	0.0175 (6)	0.0299 (7)
C9	0.0765 (10)	0.1060 (14)	0.0618 (9)	0.0620 (10)	0.0305 (8)	0.0389 (10)
C10	0.1131 (14)	0.1013 (14)	0.0517 (9)	0.0765 (12)	0.0237 (9)	0.0231 (9)
C11	0.1017 (13)	0.0676 (10)	0.0545 (9)	0.0487 (9)	0.0093 (9)	0.0153 (8)
C12	0.0703 (9)	0.0566 (8)	0.0564 (8)	0.0307 (7)	0.0122 (7)	0.0224 (7)
C13	0.0523 (7)	0.0573 (8)	0.0453 (7)	0.0300 (6)	0.0120 (6)	0.0219 (6)
C14	0.0445 (6)	0.0529 (8)	0.0474 (7)	0.0200 (6)	0.0141 (5)	0.0220 (6)
C15	0.0579 (8)	0.0502 (8)	0.0647 (9)	0.0220 (6)	0.0287 (7)	0.0244 (7)
C16	0.0411 (6)	0.0497 (7)	0.0527 (8)	0.0192 (5)	0.0220 (5)	0.0205 (6)
C17	0.0569 (8)	0.0671 (9)	0.0591 (8)	0.0262 (7)	0.0290 (6)	0.0303 (7)
C18	0.0836 (11)	0.0774 (11)	0.0891 (12)	0.0452 (9)	0.0474 (9)	0.0513 (10)
C19	0.1060 (13)	0.0592 (9)	0.1064 (15)	0.0445 (9)	0.0607 (11)	0.0415 (10)
C20	0.0872 (11)	0.0526 (8)	0.0744 (10)	0.0277 (8)	0.0401 (9)	0.0163 (8)
C21	0.0508 (7)	0.0489 (7)	0.0543 (8)	0.0194 (6)	0.0234 (6)	0.0155 (6)
C22	0.0639 (8)	0.0562 (8)	0.0450 (7)	0.0212 (7)	0.0119 (6)	0.0103 (6)
C23	0.0657 (8)	0.0585 (8)	0.0451 (7)	0.0332 (7)	0.0212 (6)	0.0246 (6)
C24	0.0968 (11)	0.0771 (10)	0.0546 (9)	0.0472 (9)	0.0390 (8)	0.0314 (8)
C25	0.1023 (13)	0.1026 (14)	0.0778 (12)	0.0643 (11)	0.0602 (10)	0.0559 (11)
C26	0.0680 (9)	0.0919 (12)	0.0898 (12)	0.0400 (9)	0.0441 (9)	0.0609 (11)
C27	0.0586 (8)	0.0636 (9)	0.0660 (9)	0.0257 (7)	0.0236 (7)	0.0365 (7)
C28	0.0509 (7)	0.0541 (7)	0.0481 (7)	0.0268 (6)	0.0193 (6)	0.0262 (6)
C29	0.0439 (6)	0.0474 (7)	0.0453 (7)	0.0183 (5)	0.0119 (5)	0.0144 (6)
C30	0.0591 (8)	0.0516 (8)	0.0559 (8)	0.0182 (6)	0.0200 (6)	0.0156 (7)

Geometric parameters (Å, º) top

N1—C14	1.2833 (16)	C12—H12A	0.9300
N1—C1	1.4082 (16)	C13—C14	1.4728 (18)
N2—C15	1.1062 (17)	C14—C15	1.4805 (19)
N3—C29	1.2804 (16)	C16—C17	1.3940 (19)
N3—C16	1.4077 (16)	C16—C21	1.3956 (19)
N4—C30	1.1348 (18)	C17—C18	1.372 (2)
C1—C2	1.3909 (19)	C17—H17A	0.9300
C1—C6	1.3936 (18)	C18—C19	1.372 (3)
C2—C3	1.373 (2)	C18—H18A	0.9300
C2—H2A	0.9300	C19—C20	1.377 (2)
C3—C4	1.369 (2)	C19—H19A	0.9300
C3—H3B	0.9300	C20—C21	1.386 (2)
C4—C5	1.370 (2)	C20—H20A	0.9300
C4—H4A	0.9300	C21—C22	1.4994 (19)
C5—C6	1.391 (2)	C22—C23	1.5008 (19)
C5—H5A	0.9300	C22—H22A	0.9700
C6—C7	1.500 (2)	C22—H22B	0.9700
C7—C8	1.500 (2)	C23—C24	1.3858 (19)
C7—H7A	0.9700	C23—C28	1.396 (2)
C7—H7B	0.9700	C24—C25	1.374 (2)
C8—C9	1.387 (2)	C24—H24A	0.9300
C8—C13	1.3980 (19)	C25—C26	1.374 (3)
C9—C10	1.375 (3)	C25—H25A	0.9300
C9—H9A	0.9300	C26—C27	1.377 (2)
C10—C11	1.369 (3)	C26—H26A	0.9300
C10—H10A	0.9300	C27—C28	1.3927 (19)
C11—C12	1.373 (2)	C27—H27A	0.9300
C11—H11A	0.9300	C28—C29	1.4735 (18)
C12—C13	1.393 (2)	C29—C30	1.4642 (19)

Cg1···Cg1ⁱ	3.673 (4)	Cg2···Cg2ⁱⁱ	3.793 (4)

C14—N1—C1	123.45 (11)	N2—C15—C14	175.67 (16)
C29—N3—C16	123.40 (10)	C17—C16—C21	119.88 (12)
C2—C1—C6	119.79 (12)	C17—C16—N3	115.52 (12)
C2—C1—N1	115.43 (11)	C21—C16—N3	124.48 (12)
C6—C1—N1	124.70 (12)	C18—C17—C16	120.68 (14)
C3—C2—C1	120.61 (14)	C18—C17—H17A	119.7
C3—C2—H2A	119.7	C16—C17—H17A	119.7
C1—C2—H2A	119.7	C17—C18—C19	119.75 (15)
C4—C3—C2	119.76 (15)	C17—C18—H18A	120.1
C4—C3—H3B	120.1	C19—C18—H18A	120.1
C2—C3—H3B	120.1	C18—C19—C20	120.00 (15)
C3—C4—C5	120.23 (14)	C18—C19—H19A	120.0
C3—C4—H4A	119.9	C20—C19—H19A	120.0
C5—C4—H4A	119.9	C19—C20—C21	121.66 (15)
C4—C5—C6	121.38 (14)	C19—C20—H20A	119.2
C4—C5—H5A	119.3	C21—C20—H20A	119.2
C6—C5—H5A	119.3	C20—C21—C16	118.00 (13)
C5—C6—C1	118.08 (14)	C20—C21—C22	122.27 (13)
C5—C6—C7	122.46 (13)	C16—C21—C22	119.73 (12)
C1—C6—C7	119.45 (12)	C21—C22—C23	109.89 (11)
C8—C7—C6	110.19 (11)	C21—C22—H22A	109.7
C8—C7—H7A	109.6	C23—C22—H22A	109.7
C6—C7—H7A	109.6	C21—C22—H22B	109.7
C8—C7—H7B	109.6	C23—C22—H22B	109.7
C6—C7—H7B	109.6	H22A—C22—H22B	108.2
H7A—C7—H7B	108.1	C24—C23—C28	118.32 (13)
C9—C8—C13	118.34 (15)	C24—C23—C22	122.21 (13)
C9—C8—C7	122.16 (14)	C28—C23—C22	119.47 (12)
C13—C8—C7	119.49 (12)	C25—C24—C23	120.81 (16)
C10—C9—C8	120.89 (16)	C25—C24—H24A	119.6
C10—C9—H9A	119.6	C23—C24—H24A	119.6
C8—C9—H9A	119.6	C26—C25—C24	120.87 (14)
C11—C10—C9	120.64 (15)	C26—C25—H25A	119.6
C11—C10—H10A	119.7	C24—C25—H25A	119.6
C9—C10—H10A	119.7	C25—C26—C27	119.47 (15)
C10—C11—C12	119.79 (16)	C25—C26—H26A	120.3
C10—C11—H11A	120.1	C27—C26—H26A	120.3
C12—C11—H11A	120.1	C26—C27—C28	120.16 (15)
C11—C12—C13	120.34 (15)	C26—C27—H27A	119.9
C11—C12—H12A	119.8	C28—C27—H27A	119.9
C13—C12—H12A	119.8	C27—C28—C23	120.32 (12)
C12—C13—C8	119.93 (13)	C27—C28—C29	119.32 (12)
C12—C13—C14	119.64 (12)	C23—C28—C29	120.34 (11)
C8—C13—C14	120.42 (12)	N3—C29—C30	113.12 (11)
N1—C14—C13	131.09 (12)	N3—C29—C28	130.40 (12)
N1—C14—C15	113.18 (11)	C30—C29—C28	116.35 (11)
C13—C14—C15	115.56 (11)	N4—C30—C29	178.61 (15)

C14—N1—C1—C2	−144.10 (13)	C29—N3—C16—C17	144.15 (12)
C14—N1—C1—C6	39.14 (19)	C29—N3—C16—C21	−39.94 (18)
C6—C1—C2—C3	−4.5 (2)	C21—C16—C17—C18	2.36 (19)
N1—C1—C2—C3	178.60 (12)	N3—C16—C17—C18	178.47 (12)
C1—C2—C3—C4	2.7 (2)	C16—C17—C18—C19	−2.1 (2)
C2—C3—C4—C5	0.7 (3)	C17—C18—C19—C20	0.7 (2)
C3—C4—C5—C6	−2.2 (3)	C18—C19—C20—C21	0.4 (3)
C4—C5—C6—C1	0.4 (2)	C19—C20—C21—C16	−0.2 (2)
C4—C5—C6—C7	179.82 (14)	C19—C20—C21—C22	−179.33 (14)
C2—C1—C6—C5	2.86 (19)	C17—C16—C21—C20	−1.19 (18)
N1—C1—C6—C5	179.49 (12)	N3—C16—C21—C20	−176.93 (12)
C2—C1—C6—C7	−176.53 (12)	C17—C16—C21—C22	177.98 (12)
N1—C1—C6—C7	0.1 (2)	N3—C16—C21—C22	2.23 (18)
C5—C6—C7—C8	114.56 (15)	C20—C21—C22—C23	−116.19 (15)
C1—C6—C7—C8	−66.07 (17)	C16—C21—C22—C23	64.68 (15)
C6—C7—C8—C9	−113.97 (14)	C21—C22—C23—C24	113.44 (15)
C6—C7—C8—C13	66.57 (16)	C21—C22—C23—C28	−66.68 (15)
C13—C8—C9—C10	1.2 (2)	C28—C23—C24—C25	−0.7 (2)
C7—C8—C9—C10	−178.22 (14)	C22—C23—C24—C25	179.17 (14)
C8—C9—C10—C11	0.7 (2)	C23—C24—C25—C26	−0.6 (2)
C9—C10—C11—C12	−1.1 (2)	C24—C25—C26—C27	0.2 (2)
C10—C11—C12—C13	−0.5 (2)	C25—C26—C27—C28	1.4 (2)
C11—C12—C13—C8	2.5 (2)	C26—C27—C28—C23	−2.72 (19)
C11—C12—C13—C14	−176.18 (12)	C26—C27—C28—C29	175.55 (12)
C9—C8—C13—C12	−2.84 (19)	C24—C23—C28—C27	2.32 (19)
C7—C8—C13—C12	176.64 (12)	C22—C23—C28—C27	−177.56 (12)
C9—C8—C13—C14	175.83 (12)	C24—C23—C28—C29	−175.94 (12)
C7—C8—C13—C14	−4.68 (18)	C22—C23—C28—C29	4.19 (18)
C1—N1—C14—C13	0.1 (2)	C16—N3—C29—C30	−177.84 (11)
C1—N1—C14—C15	175.05 (11)	C16—N3—C29—C28	−2.2 (2)
C12—C13—C14—N1	142.00 (14)	C27—C28—C29—N3	−139.03 (14)
C8—C13—C14—N1	−36.7 (2)	C23—C28—C29—N3	39.2 (2)
C12—C13—C14—C15	−32.90 (17)	C27—C28—C29—C30	36.50 (17)
C8—C13—C14—C15	148.42 (12)	C23—C28—C29—C30	−145.22 (12)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀N₂
M_r	218.25
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	10.125 (2), 10.275 (2), 12.749 (3)
α, β, γ (°)	105.96 (3), 99.18 (2), 109.04 (3)
V (Å³)	1159.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.15 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.989, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	12026, 4084, 3382
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.03
No. of reflections	4084
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.13

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Selected interatomic distances (Å) top

Cg1···Cg1ⁱ

3.673 (4)

Cg2···Cg2ⁱⁱ

3.793 (4)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z.

References

Bakker, R. A., Wieland, K., Timmerman, H. & Leurs, R. (2000). Eur. J. Pharmacol. 387, R5–R7. Web of Science CrossRef PubMed CAS Google Scholar
Bielory, L. & Ghafoor, S. (2005). Curr. Opin. Allergy Clin. Immunol. 5, 437–440. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin. Google Scholar
Li, Q.-B., Yang, W.-C., Han, Y.-J. & Zhao, X.-J. (2006). Acta Cryst. E62, o3021–o3022. Web of Science CSD CrossRef IUCr Journals Google Scholar
Schmutz, J., Hunziker, F. & Kunzle, F. (1967). Helv. Chim. Acta, 50, 245–248. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 11| November 2008| Page o2126

doi:10.1107/S1600536808033072

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