5-[(1-Benzyl-1H-1,2,3-triazol-4-yl)meth-yl]-5H-dibenzo[b,f]azepine.

In the title compound, C24H20N4, the azepine ring adopts a boat conformation. The dihedral angle between the benzene rings fused to the azepine ring is 49.40 (9)°. The triazole ring makes a dihedral angle of 77.88 (9)° with the terminal phenyl ring. In the crystal, mol-ecules are linked via C-H⋯π inter-actions and a parallel slipped π-π inter-action [centroid-centroid distance = 3.7324 (9), normal distance = 3.4060 (6) and slippage = 1.526 Å], forming a three-dimensional network.

Related literature

For the use of dibenzo azepine derivatives in the preparation of carbamazepine, see: Rockliff & Davis (1966 ▶). For their anti­tumor properties, see: Al-Qawasmeh et al. (2009 ▶). For related structures, see: Abdoh et al. (2013 ▶); Manjunath et al. (2013 ▶). For ring-puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H20N4

M = 364.44

Monoclinic,

a = 11.4339 (10) Å

b = 11.7140 (12) Å

c = 14.4527 (13) Å

β = 98.610 (4)°

V = 1913.9 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.60 mm−1

T = 296 K

0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.871, T max = 0.882

11434 measured reflections

3160 independent reflections

2742 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.135

S = 1.06

3160 reflections

242 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: Mercury (Macrae et al., 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813030547/su2664sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030547/su2664Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030547/su2664Isup3.cml

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

C24H20N4	F(000) = 768
Mr = 364.44	Dx = 1.265 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3160 reflections
a = 11.4339 (10) Å	θ = 3.9–64.7°
b = 11.7140 (12) Å	µ = 0.60 mm−1
c = 14.4527 (13) Å	T = 296 K
β = 98.610 (4)°	Block, yellow
V = 1913.9 (3) Å3	0.23 × 0.22 × 0.21 mm
Z = 4

Bruker X8 Proteum diffractometer	3160 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2742 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.029
Detector resolution: 10.7 pixels mm-1	θmax = 64.7°, θmin = 3.9°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −6→13
Tmin = 0.871, Tmax = 0.882	l = −16→16
11434 measured reflections

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.668P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3160 reflections	Δρmax = 0.37 e Å−3
242 parameters	Δρmin = −0.35 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (4)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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
N1	0.43569 (11)	0.09444 (13)	0.81026 (9)	0.0380 (4)
N2	0.75967 (14)	0.07129 (16)	0.84538 (13)	0.0587 (6)
N3	0.83816 (14)	0.15341 (17)	0.84788 (13)	0.0615 (6)
N4	0.78072 (13)	0.25199 (14)	0.84990 (10)	0.0466 (5)
C1	0.42570 (14)	0.13226 (14)	0.71500 (11)	0.0362 (5)
C2	0.50035 (15)	0.09093 (17)	0.65474 (12)	0.0444 (6)
C3	0.49640 (18)	0.13523 (19)	0.56554 (13)	0.0529 (7)
C4	0.41693 (18)	0.22002 (19)	0.53381 (13)	0.0552 (7)
C5	0.34204 (17)	0.26084 (17)	0.59263 (13)	0.0493 (6)
C6	0.34446 (15)	0.21923 (15)	0.68381 (12)	0.0397 (5)
C7	0.26469 (16)	0.26982 (16)	0.74219 (13)	0.0472 (6)
C8	0.21604 (16)	0.21843 (17)	0.80959 (14)	0.0502 (6)
C9	0.22998 (15)	0.10011 (17)	0.83926 (12)	0.0434 (6)
C10	0.33367 (14)	0.03702 (16)	0.83579 (11)	0.0390 (5)
C11	0.33787 (16)	−0.07699 (17)	0.86185 (13)	0.0486 (6)
C12	0.24221 (19)	−0.1295 (2)	0.89303 (15)	0.0606 (8)
C13	0.14115 (19)	−0.0676 (2)	0.89868 (16)	0.0654 (8)
C14	0.13561 (18)	0.0451 (2)	0.87236 (14)	0.0577 (7)
C15	0.54828 (15)	0.04203 (17)	0.85030 (13)	0.0450 (6)
C16	0.65211 (14)	0.11824 (16)	0.84764 (11)	0.0404 (6)
C17	0.66473 (15)	0.23304 (17)	0.85105 (13)	0.0473 (6)
C18	0.84716 (19)	0.3590 (2)	0.86075 (13)	0.0559 (7)
C19	0.86839 (10)	0.39520 (10)	0.96072 (6)	0.0391 (5)
C20	0.78941 (10)	0.47031 (11)	0.99293 (9)	0.0577 (7)
C21	0.80418 (14)	0.50082 (13)	1.08690 (11)	0.0767 (10)
C22	0.89793 (16)	0.45624 (15)	1.14866 (7)	0.0805 (10)
C23	0.97691 (13)	0.38113 (14)	1.11645 (8)	0.0791 (9)
C24	0.96214 (10)	0.35062 (11)	1.02248 (9)	0.0527 (7)
H2	0.55350	0.03280	0.67480	0.0530*
H3	0.54780	0.10750	0.52670	0.0630*
H4	0.41380	0.24930	0.47370	0.0660*
H5	0.28820	0.31780	0.57110	0.0590*
H7	0.24560	0.34630	0.73130	0.0570*
H8	0.16780	0.26350	0.84110	0.0600*
H11	0.40610	−0.11910	0.85840	0.0580*
H12	0.24630	−0.20610	0.91000	0.0730*
H13	0.07700	−0.10200	0.92020	0.0790*
H14	0.06700	0.08620	0.87660	0.0690*
H15A	0.55930	−0.02740	0.81610	0.0540*
H15B	0.54470	0.02110	0.91480	0.0540*
H17	0.60590	0.28730	0.85360	0.0570*
H18A	0.80330	0.41800	0.82330	0.0670*
H18B	0.92240	0.34900	0.83840	0.0670*
H20	0.72670	0.50010	0.95160	0.0690*
H21	0.75130	0.55110	1.10850	0.0920*
H22	0.90780	0.47670	1.21150	0.0970*
H23	1.03960	0.35130	1.15780	0.0950*
H24	1.01500	0.30040	1.00090	0.0630*

	U11	U22	U33	U12	U13	U23
N1	0.0325 (7)	0.0412 (8)	0.0377 (7)	−0.0023 (6)	−0.0028 (5)	0.0018 (6)
N2	0.0383 (8)	0.0599 (11)	0.0768 (12)	−0.0014 (8)	0.0054 (8)	−0.0219 (9)
N3	0.0411 (9)	0.0662 (12)	0.0775 (12)	−0.0055 (8)	0.0101 (8)	−0.0265 (9)
N4	0.0411 (8)	0.0578 (10)	0.0396 (8)	−0.0123 (7)	0.0016 (6)	−0.0084 (7)
C1	0.0342 (8)	0.0356 (9)	0.0361 (8)	−0.0059 (7)	−0.0032 (6)	−0.0037 (7)
C2	0.0399 (9)	0.0466 (11)	0.0447 (10)	−0.0010 (8)	−0.0001 (7)	−0.0063 (8)
C3	0.0518 (11)	0.0648 (14)	0.0422 (10)	−0.0080 (10)	0.0078 (8)	−0.0096 (9)
C4	0.0608 (12)	0.0639 (14)	0.0385 (10)	−0.0142 (10)	−0.0008 (9)	0.0034 (9)
C5	0.0500 (10)	0.0450 (11)	0.0478 (10)	−0.0040 (8)	−0.0091 (8)	0.0054 (8)
C6	0.0386 (9)	0.0344 (9)	0.0431 (9)	−0.0048 (7)	−0.0035 (7)	−0.0015 (7)
C7	0.0455 (10)	0.0356 (10)	0.0584 (11)	0.0037 (8)	0.0011 (8)	−0.0026 (8)
C8	0.0419 (10)	0.0499 (12)	0.0589 (11)	0.0036 (8)	0.0079 (8)	−0.0119 (9)
C9	0.0395 (9)	0.0497 (11)	0.0399 (9)	−0.0034 (8)	0.0028 (7)	−0.0061 (8)
C10	0.0374 (9)	0.0445 (11)	0.0329 (8)	−0.0062 (7)	−0.0018 (6)	−0.0020 (7)
C11	0.0439 (10)	0.0497 (12)	0.0490 (10)	−0.0051 (8)	−0.0038 (8)	0.0070 (8)
C12	0.0601 (13)	0.0582 (14)	0.0602 (12)	−0.0146 (10)	−0.0019 (10)	0.0169 (10)
C13	0.0521 (12)	0.0800 (17)	0.0652 (13)	−0.0177 (11)	0.0120 (10)	0.0137 (12)
C14	0.0428 (11)	0.0732 (15)	0.0582 (12)	−0.0036 (10)	0.0108 (9)	0.0013 (10)
C15	0.0368 (9)	0.0465 (11)	0.0478 (10)	−0.0007 (8)	−0.0066 (7)	0.0048 (8)
C16	0.0347 (9)	0.0487 (11)	0.0351 (9)	−0.0011 (7)	−0.0040 (7)	−0.0034 (7)
C17	0.0356 (9)	0.0521 (12)	0.0521 (10)	0.0000 (8)	−0.0006 (8)	0.0013 (9)
C18	0.0566 (12)	0.0647 (14)	0.0451 (10)	−0.0223 (10)	0.0032 (9)	0.0003 (9)
C19	0.0352 (8)	0.0382 (10)	0.0422 (9)	−0.0097 (7)	0.0005 (7)	0.0027 (7)
C20	0.0457 (11)	0.0518 (13)	0.0753 (14)	−0.0038 (9)	0.0080 (9)	−0.0076 (10)
C21	0.0734 (16)	0.0795 (18)	0.0832 (17)	−0.0254 (14)	0.0317 (14)	−0.0304 (14)
C22	0.107 (2)	0.088 (2)	0.0506 (13)	−0.0487 (17)	0.0250 (13)	−0.0149 (13)
C23	0.0800 (16)	0.0812 (18)	0.0630 (14)	−0.0326 (14)	−0.0319 (12)	0.0246 (13)
C24	0.0437 (10)	0.0481 (12)	0.0618 (12)	−0.0041 (8)	−0.0064 (9)	0.0076 (9)

N1—C1	1.435 (2)	C19—C20	1.3900 (17)
N1—C10	1.442 (2)	C19—C24	1.3900 (16)
N1—C15	1.465 (2)	C20—C21	1.390 (2)
N2—N3	1.312 (3)	C21—C22	1.390 (2)
N2—C16	1.352 (2)	C22—C23	1.390 (2)
N3—N4	1.331 (2)	C23—C24	1.3900 (18)
N4—C17	1.347 (2)	C2—H2	0.9300
N4—C18	1.462 (3)	C3—H3	0.9300
C1—C2	1.394 (2)	C4—H4	0.9300
C1—C6	1.407 (2)	C5—H5	0.9300
C2—C3	1.384 (3)	C7—H7	0.9300
C3—C4	1.378 (3)	C8—H8	0.9300
C4—C5	1.379 (3)	C11—H11	0.9300
C5—C6	1.401 (3)	C12—H12	0.9300
C6—C7	1.458 (3)	C13—H13	0.9300
C7—C8	1.335 (3)	C14—H14	0.9300
C8—C9	1.453 (3)	C15—H15A	0.9700
C9—C10	1.404 (2)	C15—H15B	0.9700
C9—C14	1.401 (3)	C17—H17	0.9300
C10—C11	1.387 (3)	C18—H18A	0.9700
C11—C12	1.388 (3)	C18—H18B	0.9700
C12—C13	1.377 (3)	C20—H20	0.9300
C13—C14	1.373 (3)	C21—H21	0.9300
C15—C16	1.491 (3)	C22—H22	0.9300
C16—C17	1.353 (3)	C23—H23	0.9300
C18—C19	1.490 (2)	C24—H24	0.9300
C1—N1—C10	116.01 (13)	C19—C24—C23	120.00 (12)
C1—N1—C15	116.59 (13)	C1—C2—H2	119.00
C10—N1—C15	113.59 (14)	C3—C2—H2	120.00
N3—N2—C16	108.78 (17)	C2—C3—H3	120.00
N2—N3—N4	107.39 (15)	C4—C3—H3	120.00
N3—N4—C17	110.32 (16)	C3—C4—H4	121.00
N3—N4—C18	119.74 (16)	C5—C4—H4	120.00
C17—N4—C18	129.54 (17)	C4—C5—H5	119.00
N1—C1—C2	121.60 (15)	C6—C5—H5	119.00
N1—C1—C6	119.02 (14)	C6—C7—H7	116.00
C2—C1—C6	119.21 (15)	C8—C7—H7	116.00
C1—C2—C3	120.93 (17)	C7—C8—H8	116.00
C2—C3—C4	120.55 (18)	C9—C8—H8	116.00
C3—C4—C5	118.96 (18)	C10—C11—H11	119.00
C4—C5—C6	122.16 (18)	C12—C11—H11	119.00
C1—C6—C5	118.19 (16)	C11—C12—H12	120.00
C1—C6—C7	123.32 (16)	C13—C12—H12	120.00
C5—C6—C7	118.48 (16)	C12—C13—H13	120.00
C6—C7—C8	127.16 (18)	C14—C13—H13	120.00
C7—C8—C9	127.32 (18)	C9—C14—H14	119.00
C8—C9—C10	123.20 (16)	C13—C14—H14	119.00
C8—C9—C14	118.92 (17)	N1—C15—H15A	109.00
C10—C9—C14	117.88 (18)	N1—C15—H15B	109.00
N1—C10—C9	118.91 (16)	C16—C15—H15A	109.00
N1—C10—C11	121.50 (15)	C16—C15—H15B	109.00
C9—C10—C11	119.49 (16)	H15A—C15—H15B	108.00
C10—C11—C12	121.22 (18)	N4—C17—H17	127.00
C11—C12—C13	119.7 (2)	C16—C17—H17	127.00
C12—C13—C14	119.6 (2)	N4—C18—H18A	110.00
C9—C14—C13	122.1 (2)	N4—C18—H18B	109.00
N1—C15—C16	113.27 (16)	C19—C18—H18A	109.00
N2—C16—C15	119.20 (17)	C19—C18—H18B	109.00
N2—C16—C17	108.23 (16)	H18A—C18—H18B	108.00
C15—C16—C17	132.50 (16)	C19—C20—H20	120.00
N4—C17—C16	105.26 (16)	C21—C20—H20	120.00
N4—C18—C19	110.77 (15)	C20—C21—H21	120.00
C18—C19—C20	119.02 (12)	C22—C21—H21	120.00
C18—C19—C24	120.91 (13)	C21—C22—H22	120.00
C20—C19—C24	120.00 (10)	C23—C22—H22	120.00
C19—C20—C21	120.00 (12)	C22—C23—H23	120.00
C20—C21—C22	120.00 (14)	C24—C23—H23	120.00
C21—C22—C23	120.00 (11)	C19—C24—H24	120.00
C22—C23—C24	120.00 (12)	C23—C24—H24	120.00
C10—N1—C1—C2	−118.27 (18)	C1—C6—C7—C8	−32.0 (3)
C10—N1—C1—C6	66.5 (2)	C5—C6—C7—C8	149.4 (2)
C15—N1—C1—C2	19.7 (2)	C6—C7—C8—C9	−1.0 (3)
C15—N1—C1—C6	−155.60 (16)	C7—C8—C9—C10	31.6 (3)
C1—N1—C10—C9	−68.6 (2)	C7—C8—C9—C14	−147.9 (2)
C1—N1—C10—C11	114.98 (18)	C8—C9—C10—N1	6.2 (3)
C15—N1—C10—C9	152.20 (15)	C8—C9—C10—C11	−177.34 (17)
C15—N1—C10—C11	−24.2 (2)	C14—C9—C10—N1	−174.34 (16)
C1—N1—C15—C16	57.8 (2)	C14—C9—C10—C11	2.1 (3)
C10—N1—C15—C16	−163.24 (14)	C8—C9—C14—C13	177.84 (19)
C16—N2—N3—N4	−1.2 (2)	C10—C9—C14—C13	−1.7 (3)
N3—N2—C16—C15	−176.98 (16)	N1—C10—C11—C12	175.13 (17)
N3—N2—C16—C17	0.4 (2)	C9—C10—C11—C12	−1.2 (3)
N2—N3—N4—C17	1.5 (2)	C10—C11—C12—C13	−0.2 (3)
N2—N3—N4—C18	174.94 (16)	C11—C12—C13—C14	0.8 (3)
N3—N4—C17—C16	−1.3 (2)	C12—C13—C14—C9	0.2 (3)
C18—N4—C17—C16	−173.84 (16)	N1—C15—C16—N2	−153.38 (16)
N3—N4—C18—C19	−95.86 (19)	N1—C15—C16—C17	30.0 (3)
C17—N4—C18—C19	76.1 (2)	N2—C16—C17—N4	0.5 (2)
N1—C1—C2—C3	−174.45 (17)	C15—C16—C17—N4	177.41 (17)
C6—C1—C2—C3	0.8 (3)	N4—C18—C19—C20	−93.75 (18)
N1—C1—C6—C5	175.42 (16)	N4—C18—C19—C24	83.06 (19)
N1—C1—C6—C7	−3.2 (3)	C18—C19—C20—C21	176.83 (15)
C2—C1—C6—C5	0.1 (2)	C24—C19—C20—C21	−0.02 (19)
C2—C1—C6—C7	−178.55 (17)	C18—C19—C24—C23	−176.77 (15)
C1—C2—C3—C4	−1.1 (3)	C20—C19—C24—C23	0.0 (2)
C2—C3—C4—C5	0.6 (3)	C19—C20—C21—C22	0.0 (2)
C3—C4—C5—C6	0.3 (3)	C20—C21—C22—C23	0.0 (2)
C4—C5—C6—C1	−0.6 (3)	C21—C22—C23—C24	0.0 (2)
C4—C5—C6—C7	178.08 (18)	C22—C23—C24—C19	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···Cg2i	0.97	2.83	3.600 (2)	137
C20—H20···Cg1i	0.93	2.79	3.642 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯Cg2i	0.97	2.83	3.600 (2)	137
C20—H20⋯Cg1i	0.93	2.79	3.642 (2)	153

Symmetry code: (i) .