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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2126.
Published online 2008 October 18. doi:  10.1107/S1600536808033072
PMCID: PMC2959734

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

Abstract

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 [triangle]); Bielory & Ghafoor (2005 [triangle]); Schmutz et al. (1967 [triangle]). For a similar structure, see: Li et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2126-scheme1.jpg

Experimental

Crystal data

  • C15H10N2
  • M r = 218.25
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2126-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.097
  • S = 1.03
  • 4084 reflections
  • 308 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.13 e Å−3

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

Table 1
Selected interatomic distances (Å)

Supplementary Material

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

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

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

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

All H atoms were placed in calculated positions, with C—H = 0.93 or 0.97 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2 times Ueq(C).

Figures

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

Crystal data

C15H10N2Z = 4
Mr = 218.25F(000) = 456
Triclinic, P1Dx = 1.251 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.125 (2) ÅCell parameters from 4851 reflections
b = 10.275 (2) Åθ = 2.2–28.0°
c = 12.749 (3) ŵ = 0.08 mm1
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

Bruker SMART CCD area-detector diffractometer4084 independent reflections
Radiation source: fine-focus sealed tube3382 reflections with I > 2σ(I)
graphiteRint = 0.021
[var phi] and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.989, Tmax = 0.993k = −12→12
12026 measured reflectionsl = −14→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.097w = 1/[σ2(Fo2) + (0.0446P)2 + 0.1613P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4084 reflectionsΔρmax = 0.19 e Å3
308 parametersΔρmin = −0.13 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.037 (2)

Special details

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)

xyzUiso*/Ueq
N10.93668 (11)0.20617 (11)0.18911 (9)0.0486 (3)
N21.10390 (18)0.47578 (17)0.10411 (14)0.0874 (4)
N30.33399 (10)0.33411 (11)0.30617 (9)0.0474 (3)
N40.42697 (16)0.69062 (15)0.35893 (13)0.0816 (4)
C10.87147 (12)0.11423 (13)0.24622 (10)0.0466 (3)
C20.93247 (14)0.01429 (14)0.25883 (12)0.0568 (3)
H2A1.00960.01050.22880.068*
C30.87991 (17)−0.07883 (16)0.31523 (14)0.0699 (4)
H3B0.9238−0.14250.32610.084*
C40.76259 (18)−0.07763 (18)0.35547 (14)0.0747 (5)
H4A0.7275−0.13990.39440.090*
C50.69679 (16)0.01499 (17)0.33859 (13)0.0679 (4)
H5A0.61510.01220.36400.082*
C60.74956 (13)0.11314 (15)0.28418 (11)0.0532 (3)
C70.67936 (14)0.21544 (17)0.26432 (13)0.0644 (4)
H7A0.65530.20130.18410.077*
H7B0.59000.19360.28710.077*
C80.78013 (14)0.37191 (16)0.33094 (11)0.0549 (3)
C90.74955 (18)0.4600 (2)0.41954 (13)0.0707 (4)
H9A0.66530.42100.44030.085*
C100.8421 (2)0.6044 (2)0.47717 (14)0.0800 (5)
H10A0.82040.66150.53690.096*
C110.9659 (2)0.66483 (19)0.44740 (13)0.0732 (4)
H11A1.02710.76300.48590.088*
C120.99953 (16)0.58006 (15)0.36048 (12)0.0596 (4)
H12A1.08320.62130.33980.071*
C130.90890 (13)0.43261 (14)0.30305 (10)0.0486 (3)
C140.95118 (13)0.34087 (14)0.21488 (10)0.0469 (3)
C151.03427 (15)0.41783 (15)0.14911 (12)0.0549 (3)
C160.30864 (12)0.18357 (13)0.26934 (11)0.0457 (3)
C170.32200 (14)0.12481 (16)0.35496 (12)0.0570 (3)
H17A0.34850.18540.43050.068*
C180.29646 (18)−0.02147 (18)0.32903 (16)0.0717 (4)
H18A0.3087−0.05910.38670.086*
C190.2528 (2)−0.11204 (18)0.21765 (17)0.0804 (5)
H19A0.2344−0.21150.19970.097*
C200.23630 (18)−0.05569 (16)0.13243 (15)0.0703 (4)
H20A0.2060−0.11840.05730.084*
C210.26371 (13)0.09205 (14)0.15582 (11)0.0508 (3)
C220.24469 (15)0.15472 (15)0.06392 (11)0.0577 (4)
H22A0.17730.20290.07390.069*
H22B0.20460.0762−0.00950.069*
C230.38852 (15)0.26340 (15)0.06805 (11)0.0518 (3)
C240.45555 (19)0.23862 (18)−0.01782 (13)0.0684 (4)
H24A0.41140.1515−0.08000.082*
C250.5865 (2)0.3412 (2)−0.01221 (15)0.0777 (5)
H25A0.63020.3222−0.07040.093*
C260.65358 (17)0.4714 (2)0.07818 (15)0.0715 (4)
H26A0.74200.54020.08110.086*
C270.58889 (15)0.49905 (16)0.16430 (13)0.0583 (4)
H27A0.63260.58790.22490.070*
C280.45808 (13)0.39437 (14)0.16093 (11)0.0467 (3)
C290.39603 (13)0.42144 (13)0.25784 (10)0.0459 (3)
C300.41483 (15)0.57366 (16)0.31439 (12)0.0566 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0475 (6)0.0505 (6)0.0503 (6)0.0185 (5)0.0175 (5)0.0198 (5)
N20.0998 (11)0.0880 (10)0.0966 (11)0.0383 (9)0.0484 (9)0.0511 (9)
N30.0454 (5)0.0503 (6)0.0456 (6)0.0166 (5)0.0171 (5)0.0152 (5)
N40.0931 (10)0.0557 (8)0.0875 (10)0.0253 (7)0.0296 (8)0.0140 (7)
C10.0414 (6)0.0468 (7)0.0461 (7)0.0105 (5)0.0116 (5)0.0163 (6)
C20.0511 (7)0.0501 (8)0.0691 (9)0.0171 (6)0.0189 (6)0.0229 (7)
C30.0716 (9)0.0565 (9)0.0850 (11)0.0206 (7)0.0198 (8)0.0363 (8)
C40.0769 (10)0.0655 (10)0.0781 (11)0.0102 (8)0.0259 (9)0.0385 (9)
C50.0525 (8)0.0725 (10)0.0725 (10)0.0095 (7)0.0263 (7)0.0289 (8)
C60.0393 (6)0.0592 (8)0.0535 (8)0.0112 (6)0.0119 (6)0.0184 (6)
C70.0404 (7)0.0874 (11)0.0719 (10)0.0274 (7)0.0195 (7)0.0325 (8)
C80.0533 (7)0.0761 (9)0.0526 (8)0.0391 (7)0.0175 (6)0.0299 (7)
C90.0765 (10)0.1060 (14)0.0618 (9)0.0620 (10)0.0305 (8)0.0389 (10)
C100.1131 (14)0.1013 (14)0.0517 (9)0.0765 (12)0.0237 (9)0.0231 (9)
C110.1017 (13)0.0676 (10)0.0545 (9)0.0487 (9)0.0093 (9)0.0153 (8)
C120.0703 (9)0.0566 (8)0.0564 (8)0.0307 (7)0.0122 (7)0.0224 (7)
C130.0523 (7)0.0573 (8)0.0453 (7)0.0300 (6)0.0120 (6)0.0219 (6)
C140.0445 (6)0.0529 (8)0.0474 (7)0.0200 (6)0.0141 (5)0.0220 (6)
C150.0579 (8)0.0502 (8)0.0647 (9)0.0220 (6)0.0287 (7)0.0244 (7)
C160.0411 (6)0.0497 (7)0.0527 (8)0.0192 (5)0.0220 (5)0.0205 (6)
C170.0569 (8)0.0671 (9)0.0591 (8)0.0262 (7)0.0290 (6)0.0303 (7)
C180.0836 (11)0.0774 (11)0.0891 (12)0.0452 (9)0.0474 (9)0.0513 (10)
C190.1060 (13)0.0592 (9)0.1064 (15)0.0445 (9)0.0607 (11)0.0415 (10)
C200.0872 (11)0.0526 (8)0.0744 (10)0.0277 (8)0.0401 (9)0.0163 (8)
C210.0508 (7)0.0489 (7)0.0543 (8)0.0194 (6)0.0234 (6)0.0155 (6)
C220.0639 (8)0.0562 (8)0.0450 (7)0.0212 (7)0.0119 (6)0.0103 (6)
C230.0657 (8)0.0585 (8)0.0451 (7)0.0332 (7)0.0212 (6)0.0246 (6)
C240.0968 (11)0.0771 (10)0.0546 (9)0.0472 (9)0.0390 (8)0.0314 (8)
C250.1023 (13)0.1026 (14)0.0778 (12)0.0643 (11)0.0602 (10)0.0559 (11)
C260.0680 (9)0.0919 (12)0.0898 (12)0.0400 (9)0.0441 (9)0.0609 (11)
C270.0586 (8)0.0636 (9)0.0660 (9)0.0257 (7)0.0236 (7)0.0365 (7)
C280.0509 (7)0.0541 (7)0.0481 (7)0.0268 (6)0.0193 (6)0.0262 (6)
C290.0439 (6)0.0474 (7)0.0453 (7)0.0183 (5)0.0119 (5)0.0144 (6)
C300.0591 (8)0.0516 (8)0.0559 (8)0.0182 (6)0.0200 (6)0.0156 (7)

Geometric parameters (Å, °)

N1—C141.2833 (16)C12—H12A0.9300
N1—C11.4082 (16)C13—C141.4728 (18)
N2—C151.1062 (17)C14—C151.4805 (19)
N3—C291.2804 (16)C16—C171.3940 (19)
N3—C161.4077 (16)C16—C211.3956 (19)
N4—C301.1348 (18)C17—C181.372 (2)
C1—C21.3909 (19)C17—H17A0.9300
C1—C61.3936 (18)C18—C191.372 (3)
C2—C31.373 (2)C18—H18A0.9300
C2—H2A0.9300C19—C201.377 (2)
C3—C41.369 (2)C19—H19A0.9300
C3—H3B0.9300C20—C211.386 (2)
C4—C51.370 (2)C20—H20A0.9300
C4—H4A0.9300C21—C221.4994 (19)
C5—C61.391 (2)C22—C231.5008 (19)
C5—H5A0.9300C22—H22A0.9700
C6—C71.500 (2)C22—H22B0.9700
C7—C81.500 (2)C23—C241.3858 (19)
C7—H7A0.9700C23—C281.396 (2)
C7—H7B0.9700C24—C251.374 (2)
C8—C91.387 (2)C24—H24A0.9300
C8—C131.3980 (19)C25—C261.374 (3)
C9—C101.375 (3)C25—H25A0.9300
C9—H9A0.9300C26—C271.377 (2)
C10—C111.369 (3)C26—H26A0.9300
C10—H10A0.9300C27—C281.3927 (19)
C11—C121.373 (2)C27—H27A0.9300
C11—H11A0.9300C28—C291.4735 (18)
C12—C131.393 (2)C29—C301.4642 (19)
Cg1···Cg1i3.673 (4)Cg2···Cg2ii3.793 (4)
C14—N1—C1123.45 (11)N2—C15—C14175.67 (16)
C29—N3—C16123.40 (10)C17—C16—C21119.88 (12)
C2—C1—C6119.79 (12)C17—C16—N3115.52 (12)
C2—C1—N1115.43 (11)C21—C16—N3124.48 (12)
C6—C1—N1124.70 (12)C18—C17—C16120.68 (14)
C3—C2—C1120.61 (14)C18—C17—H17A119.7
C3—C2—H2A119.7C16—C17—H17A119.7
C1—C2—H2A119.7C17—C18—C19119.75 (15)
C4—C3—C2119.76 (15)C17—C18—H18A120.1
C4—C3—H3B120.1C19—C18—H18A120.1
C2—C3—H3B120.1C18—C19—C20120.00 (15)
C3—C4—C5120.23 (14)C18—C19—H19A120.0
C3—C4—H4A119.9C20—C19—H19A120.0
C5—C4—H4A119.9C19—C20—C21121.66 (15)
C4—C5—C6121.38 (14)C19—C20—H20A119.2
C4—C5—H5A119.3C21—C20—H20A119.2
C6—C5—H5A119.3C20—C21—C16118.00 (13)
C5—C6—C1118.08 (14)C20—C21—C22122.27 (13)
C5—C6—C7122.46 (13)C16—C21—C22119.73 (12)
C1—C6—C7119.45 (12)C21—C22—C23109.89 (11)
C8—C7—C6110.19 (11)C21—C22—H22A109.7
C8—C7—H7A109.6C23—C22—H22A109.7
C6—C7—H7A109.6C21—C22—H22B109.7
C8—C7—H7B109.6C23—C22—H22B109.7
C6—C7—H7B109.6H22A—C22—H22B108.2
H7A—C7—H7B108.1C24—C23—C28118.32 (13)
C9—C8—C13118.34 (15)C24—C23—C22122.21 (13)
C9—C8—C7122.16 (14)C28—C23—C22119.47 (12)
C13—C8—C7119.49 (12)C25—C24—C23120.81 (16)
C10—C9—C8120.89 (16)C25—C24—H24A119.6
C10—C9—H9A119.6C23—C24—H24A119.6
C8—C9—H9A119.6C26—C25—C24120.87 (14)
C11—C10—C9120.64 (15)C26—C25—H25A119.6
C11—C10—H10A119.7C24—C25—H25A119.6
C9—C10—H10A119.7C25—C26—C27119.47 (15)
C10—C11—C12119.79 (16)C25—C26—H26A120.3
C10—C11—H11A120.1C27—C26—H26A120.3
C12—C11—H11A120.1C26—C27—C28120.16 (15)
C11—C12—C13120.34 (15)C26—C27—H27A119.9
C11—C12—H12A119.8C28—C27—H27A119.9
C13—C12—H12A119.8C27—C28—C23120.32 (12)
C12—C13—C8119.93 (13)C27—C28—C29119.32 (12)
C12—C13—C14119.64 (12)C23—C28—C29120.34 (11)
C8—C13—C14120.42 (12)N3—C29—C30113.12 (11)
N1—C14—C13131.09 (12)N3—C29—C28130.40 (12)
N1—C14—C15113.18 (11)C30—C29—C28116.35 (11)
C13—C14—C15115.56 (11)N4—C30—C29178.61 (15)
C14—N1—C1—C2−144.10 (13)C29—N3—C16—C17144.15 (12)
C14—N1—C1—C639.14 (19)C29—N3—C16—C21−39.94 (18)
C6—C1—C2—C3−4.5 (2)C21—C16—C17—C182.36 (19)
N1—C1—C2—C3178.60 (12)N3—C16—C17—C18178.47 (12)
C1—C2—C3—C42.7 (2)C16—C17—C18—C19−2.1 (2)
C2—C3—C4—C50.7 (3)C17—C18—C19—C200.7 (2)
C3—C4—C5—C6−2.2 (3)C18—C19—C20—C210.4 (3)
C4—C5—C6—C10.4 (2)C19—C20—C21—C16−0.2 (2)
C4—C5—C6—C7179.82 (14)C19—C20—C21—C22−179.33 (14)
C2—C1—C6—C52.86 (19)C17—C16—C21—C20−1.19 (18)
N1—C1—C6—C5179.49 (12)N3—C16—C21—C20−176.93 (12)
C2—C1—C6—C7−176.53 (12)C17—C16—C21—C22177.98 (12)
N1—C1—C6—C70.1 (2)N3—C16—C21—C222.23 (18)
C5—C6—C7—C8114.56 (15)C20—C21—C22—C23−116.19 (15)
C1—C6—C7—C8−66.07 (17)C16—C21—C22—C2364.68 (15)
C6—C7—C8—C9−113.97 (14)C21—C22—C23—C24113.44 (15)
C6—C7—C8—C1366.57 (16)C21—C22—C23—C28−66.68 (15)
C13—C8—C9—C101.2 (2)C28—C23—C24—C25−0.7 (2)
C7—C8—C9—C10−178.22 (14)C22—C23—C24—C25179.17 (14)
C8—C9—C10—C110.7 (2)C23—C24—C25—C26−0.6 (2)
C9—C10—C11—C12−1.1 (2)C24—C25—C26—C270.2 (2)
C10—C11—C12—C13−0.5 (2)C25—C26—C27—C281.4 (2)
C11—C12—C13—C82.5 (2)C26—C27—C28—C23−2.72 (19)
C11—C12—C13—C14−176.18 (12)C26—C27—C28—C29175.55 (12)
C9—C8—C13—C12−2.84 (19)C24—C23—C28—C272.32 (19)
C7—C8—C13—C12176.64 (12)C22—C23—C28—C27−177.56 (12)
C9—C8—C13—C14175.83 (12)C24—C23—C28—C29−175.94 (12)
C7—C8—C13—C14−4.68 (18)C22—C23—C28—C294.19 (18)
C1—N1—C14—C130.1 (2)C16—N3—C29—C30−177.84 (11)
C1—N1—C14—C15175.05 (11)C16—N3—C29—C28−2.2 (2)
C12—C13—C14—N1142.00 (14)C27—C28—C29—N3−139.03 (14)
C8—C13—C14—N1−36.7 (2)C23—C28—C29—N339.2 (2)
C12—C13—C14—C15−32.90 (17)C27—C28—C29—C3036.50 (17)
C8—C13—C14—C15148.42 (12)C23—C28—C29—C30−145.22 (12)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2271).

References

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