1,1'-[(2,3,3a,4,5,6,7,7a-Octa-hydro-1H-1,3-benzimidazole-1,3-di-yl)bis-(methyl-ene)]bis-(1H-benzotriazole).

The cyclo-hexane ring in the title compound, C(21)H(24)N(8), adopts a chair conformation and the five-membered heterocyclic ring to which it is fused adopts a twist conformation on their common C-C bond. The substituents on the N atoms of the central five-membered heterocycle are arranged trans with respect to the central ring. The terminal benzotriazole rings are oriented at angles of 74.66 (8) and 84.18 (8)° with respect to the mean plane of the central heterocycle. The angle between the two benzotriazole rings is 30.80 (9)°. The bond lengths and angles are within normal ranges; the largest deviation from expecta-tion is for a long N-CH(2) bond length [1.476 (2) Å] as a consequence of an anomeric effect. In the crystal, mol-ecules are connected by C-H⋯N hydrogen bonds.

Related literature

For general background to anomeric effects, see: Carey & Sundberg (2000 ▶). For related structures see: Rivera et al. (2011 ▶); Wang et al. (2008 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H24N8

M = 388.48

Monoclinic,

a = 11.9474 (2) Å

b = 5.9406 (1) Å

c = 27.3861 (4) Å

β = 90.861 (1)°

V = 1943.50 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 120 K

0.31 × 0.18 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

37999 measured reflections

3461 independent reflections

2990 reflections with I > 2σ(I)

R int = 0.172

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.137

S = 1.06

3461 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104044X/bh2381sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104044X/bh2381Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104044X/bh2381Isup3.cml

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

C21H24N8	F(000) = 824
Mr = 388.48	Dx = 1.328 Mg m−3
Monoclinic, P21/c	Melting point: 424 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.5418 Å
a = 11.9474 (2) Å	Cell parameters from 13493 reflections
b = 5.9406 (1) Å	θ = 3.2°
c = 27.3861 (4) Å	µ = 0.68 mm−1
β = 90.861 (1)°	T = 120 K
V = 1943.50 (5) Å3	Plate, colourless
Z = 4	0.31 × 0.18 × 0.11 mm

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	2990 reflections with I > 2σ(I)
Radiation source: Enhance Ultra (Cu) X-ray Source	Rint = 0.172
mirror	θmax = 67.1°, θmin = 3.2°
Detector resolution: 10.3784 pixels mm-1	h = −14→14
Rotation method data acquisition using ω scans	k = −7→7
37999 measured reflections	l = −32→32
3461 independent reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0756P)2 + 0.4705P] where P = (Fo2 + 2Fc2)/3
3461 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.31 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
N1	0.06576 (12)	1.3038 (2)	0.03014 (5)	0.0301 (4)
N2	0.06561 (12)	1.1599 (2)	0.06570 (5)	0.0298 (3)
N3	0.12624 (11)	0.9755 (2)	0.05292 (5)	0.0256 (3)
N4	0.21777 (12)	0.7711 (2)	0.12114 (5)	0.0277 (3)
N5	0.34776 (11)	0.9703 (2)	0.16832 (5)	0.0250 (3)
N6	0.31150 (11)	0.9133 (2)	0.25550 (5)	0.0240 (3)
N7	0.34948 (11)	0.7097 (3)	0.27089 (5)	0.0296 (4)
N8	0.27753 (12)	0.6222 (3)	0.30094 (5)	0.0302 (3)
C1	0.12747 (13)	1.2136 (3)	−0.00732 (6)	0.0249 (4)
C2	0.14940 (14)	1.3000 (3)	−0.05407 (6)	0.0293 (4)
H2	0.1233	1.4406	−0.0639	0.035*
C3	0.21134 (15)	1.1660 (3)	−0.08439 (7)	0.0332 (4)
H3	0.2266	1.2157	−0.1158	0.040*
C4	0.25227 (15)	0.9548 (3)	−0.06892 (7)	0.0334 (4)
H4	0.2949	0.8705	−0.0904	0.040*
C5	0.23166 (14)	0.8690 (3)	−0.02351 (7)	0.0299 (4)
H5	0.2591	0.7296	−0.0136	0.036*
C6	0.16690 (13)	1.0034 (3)	0.00695 (6)	0.0239 (4)
C7	0.12758 (14)	0.7809 (3)	0.08616 (7)	0.0288 (4)
H7A	0.0577	0.7797	0.1038	0.035*
H7B	0.1296	0.6450	0.0666	0.035*
C8	0.22853 (13)	0.9669 (3)	0.15340 (6)	0.0270 (4)
H8A	0.1810	0.9509	0.1816	0.032*
H8B	0.2083	1.1041	0.1362	0.032*
C9	0.33087 (14)	0.7201 (3)	0.10497 (6)	0.0265 (4)
H9	0.3541	0.8339	0.0813	0.032*
C10	0.35246 (16)	0.4874 (3)	0.08427 (7)	0.0350 (4)
H10A	0.3126	0.4691	0.0534	0.042*
H10B	0.3265	0.3730	0.1067	0.042*
C11	0.47850 (16)	0.4632 (3)	0.07680 (8)	0.0391 (5)
H11A	0.5017	0.5670	0.0515	0.047*
H11B	0.4945	0.3117	0.0657	0.047*
C12	0.54586 (16)	0.5107 (3)	0.12368 (8)	0.0391 (5)
H12A	0.6251	0.5020	0.1167	0.047*
H12B	0.5292	0.3956	0.1476	0.047*
C13	0.51985 (14)	0.7429 (3)	0.14530 (7)	0.0338 (4)
H13A	0.5590	0.7621	0.1763	0.041*
H13B	0.5437	0.8607	0.1233	0.041*
C14	0.39463 (14)	0.7551 (3)	0.15242 (6)	0.0265 (4)
H14	0.3728	0.6377	0.1755	0.032*
C15	0.37030 (13)	1.0415 (3)	0.21750 (6)	0.0270 (4)
H15A	0.3498	1.1989	0.2204	0.032*
H15B	0.4502	1.0302	0.2238	0.032*
C16	0.21029 (13)	0.9579 (3)	0.27606 (6)	0.0235 (4)
C17	0.13513 (14)	1.1384 (3)	0.27189 (6)	0.0284 (4)
H17	0.1497	1.2636	0.2526	0.034*
C18	0.03858 (15)	1.1180 (3)	0.29813 (7)	0.0333 (4)
H18	−0.0144	1.2324	0.2960	0.040*
C19	0.01666 (14)	0.9313 (3)	0.32806 (6)	0.0313 (4)
H19	−0.0497	0.9267	0.3454	0.038*
C20	0.09064 (14)	0.7563 (3)	0.33234 (6)	0.0297 (4)
H20	0.0762	0.6333	0.3523	0.036*
C21	0.18967 (14)	0.7708 (3)	0.30514 (6)	0.0255 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0331 (8)	0.0264 (8)	0.0309 (8)	0.0061 (6)	−0.0009 (6)	−0.0036 (6)
N2	0.0288 (7)	0.0288 (8)	0.0320 (8)	0.0062 (6)	0.0007 (6)	−0.0046 (6)
N3	0.0240 (7)	0.0252 (7)	0.0275 (8)	0.0008 (5)	0.0001 (6)	−0.0031 (6)
N4	0.0231 (7)	0.0284 (8)	0.0316 (8)	−0.0020 (5)	−0.0018 (6)	0.0023 (6)
N5	0.0199 (7)	0.0294 (8)	0.0258 (8)	−0.0033 (5)	0.0033 (5)	0.0013 (6)
N6	0.0203 (6)	0.0282 (7)	0.0233 (7)	−0.0007 (5)	0.0004 (5)	0.0026 (5)
N7	0.0238 (7)	0.0329 (8)	0.0320 (8)	0.0046 (6)	0.0004 (6)	0.0050 (6)
N8	0.0263 (7)	0.0314 (8)	0.0329 (8)	0.0032 (6)	0.0028 (6)	0.0057 (6)
C1	0.0228 (8)	0.0221 (8)	0.0298 (9)	−0.0012 (6)	−0.0019 (6)	−0.0047 (6)
C2	0.0281 (8)	0.0257 (9)	0.0338 (10)	−0.0039 (7)	−0.0051 (7)	0.0021 (7)
C3	0.0281 (9)	0.0409 (10)	0.0308 (9)	−0.0068 (7)	0.0025 (7)	0.0020 (8)
C4	0.0283 (9)	0.0375 (10)	0.0345 (10)	0.0027 (7)	0.0063 (7)	−0.0074 (8)
C5	0.0267 (8)	0.0271 (9)	0.0361 (10)	0.0033 (7)	0.0018 (7)	−0.0047 (7)
C6	0.0204 (7)	0.0258 (8)	0.0255 (9)	−0.0025 (6)	−0.0025 (6)	−0.0034 (6)
C7	0.0256 (8)	0.0261 (9)	0.0345 (10)	−0.0034 (6)	−0.0024 (7)	0.0021 (7)
C8	0.0218 (8)	0.0345 (9)	0.0247 (9)	−0.0010 (7)	0.0016 (6)	0.0004 (7)
C9	0.0249 (8)	0.0247 (9)	0.0299 (9)	−0.0019 (6)	0.0020 (7)	0.0035 (7)
C10	0.0373 (10)	0.0263 (9)	0.0412 (11)	0.0003 (7)	−0.0049 (8)	−0.0014 (8)
C11	0.0403 (11)	0.0298 (10)	0.0473 (12)	0.0066 (8)	0.0055 (9)	−0.0036 (8)
C12	0.0282 (9)	0.0362 (11)	0.0530 (13)	0.0040 (8)	0.0008 (8)	0.0004 (9)
C13	0.0230 (9)	0.0353 (10)	0.0431 (11)	−0.0004 (7)	0.0007 (7)	0.0002 (8)
C14	0.0236 (8)	0.0259 (9)	0.0299 (9)	−0.0024 (6)	0.0028 (7)	0.0046 (7)
C15	0.0223 (8)	0.0304 (9)	0.0283 (9)	−0.0073 (6)	0.0021 (6)	0.0022 (7)
C16	0.0204 (8)	0.0276 (9)	0.0225 (8)	−0.0011 (6)	−0.0003 (6)	−0.0027 (6)
C17	0.0319 (9)	0.0243 (9)	0.0291 (9)	0.0023 (7)	0.0012 (7)	−0.0005 (7)
C18	0.0324 (9)	0.0346 (10)	0.0330 (10)	0.0088 (7)	0.0013 (7)	−0.0074 (7)
C19	0.0252 (8)	0.0393 (10)	0.0297 (10)	−0.0011 (7)	0.0067 (7)	−0.0085 (7)
C20	0.0284 (9)	0.0333 (10)	0.0274 (9)	−0.0055 (7)	0.0037 (7)	0.0010 (7)
C21	0.0247 (8)	0.0268 (9)	0.0250 (9)	0.0005 (6)	0.0006 (6)	0.0004 (6)

N1—N2	1.296 (2)	C8—H8B	0.9700
N1—C1	1.380 (2)	C9—C14	1.511 (2)
N2—N3	1.3619 (19)	C9—C10	1.517 (2)
N3—C6	1.366 (2)	C9—H9	0.9800
N3—C7	1.471 (2)	C10—C11	1.529 (3)
N4—C7	1.432 (2)	C10—H10A	0.9700
N4—C9	1.460 (2)	C10—H10B	0.9700
N4—C8	1.465 (2)	C11—C12	1.531 (3)
N5—C15	1.433 (2)	C11—H11A	0.9700
N5—C14	1.464 (2)	C11—H11B	0.9700
N5—C8	1.476 (2)	C12—C13	1.535 (3)
N6—N7	1.357 (2)	C12—H12A	0.9700
N6—C16	1.367 (2)	C12—H12B	0.9700
N6—C15	1.476 (2)	C13—C14	1.513 (2)
N7—N8	1.307 (2)	C13—H13A	0.9700
N8—C21	1.378 (2)	C13—H13B	0.9700
C1—C6	1.389 (2)	C14—H14	0.9800
C1—C2	1.408 (2)	C15—H15A	0.9700
C2—C3	1.375 (3)	C15—H15B	0.9700
C2—H2	0.9300	C16—C21	1.391 (2)
C3—C4	1.409 (3)	C16—C17	1.402 (2)
C3—H3	0.9300	C17—C18	1.374 (2)
C4—C5	1.370 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.406 (3)
C5—C6	1.397 (2)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.369 (3)
C7—H7A	0.9700	C19—H19	0.9300
C7—H7B	0.9700	C20—C21	1.410 (2)
C8—H8A	0.9700	C20—H20	0.9300
N2—N1—C1	108.00 (14)	C9—C10—H10A	110.1
N1—N2—N3	109.32 (13)	C11—C10—H10A	110.1
N2—N3—C6	109.70 (13)	C9—C10—H10B	110.1
N2—N3—C7	118.30 (13)	C11—C10—H10B	110.1
C6—N3—C7	131.64 (14)	H10A—C10—H10B	108.4
C7—N4—C9	119.73 (14)	C10—C11—C12	112.13 (16)
C7—N4—C8	115.44 (13)	C10—C11—H11A	109.2
C9—N4—C8	105.94 (13)	C12—C11—H11A	109.2
C15—N5—C14	118.03 (14)	C10—C11—H11B	109.2
C15—N5—C8	115.53 (13)	C12—C11—H11B	109.2
C14—N5—C8	106.11 (13)	H11A—C11—H11B	107.9
N7—N6—C16	109.79 (13)	C11—C12—C13	112.45 (16)
N7—N6—C15	121.24 (13)	C11—C12—H12A	109.1
C16—N6—C15	128.57 (14)	C13—C12—H12A	109.1
N8—N7—N6	109.28 (13)	C11—C12—H12B	109.1
N7—N8—C21	107.87 (14)	C13—C12—H12B	109.1
N1—C1—C6	108.83 (15)	H12A—C12—H12B	107.8
N1—C1—C2	130.01 (16)	C14—C13—C12	107.41 (14)
C6—C1—C2	121.12 (16)	C14—C13—H13A	110.2
C3—C2—C1	116.57 (16)	C12—C13—H13A	110.2
C3—C2—H2	121.7	C14—C13—H13B	110.2
C1—C2—H2	121.7	C12—C13—H13B	110.2
C2—C3—C4	121.44 (17)	H13A—C13—H13B	108.5
C2—C3—H3	119.3	N5—C14—C9	100.73 (13)
C4—C3—H3	119.3	N5—C14—C13	117.62 (14)
C5—C4—C3	122.54 (17)	C9—C14—C13	111.67 (14)
C5—C4—H4	118.7	N5—C14—H14	108.8
C3—C4—H4	118.7	C9—C14—H14	108.8
C4—C5—C6	115.99 (16)	C13—C14—H14	108.8
C4—C5—H5	122.0	N5—C15—N6	115.18 (13)
C6—C5—H5	122.0	N5—C15—H15A	108.5
N3—C6—C1	104.14 (14)	N6—C15—H15A	108.5
N3—C6—C5	133.54 (16)	N5—C15—H15B	108.5
C1—C6—C5	122.31 (16)	N6—C15—H15B	108.5
N4—C7—N3	116.54 (13)	H15A—C15—H15B	107.5
N4—C7—H7A	108.2	N6—C16—C21	104.25 (14)
N3—C7—H7A	108.2	N6—C16—C17	133.15 (15)
N4—C7—H7B	108.2	C21—C16—C17	122.59 (15)
N3—C7—H7B	108.2	C18—C17—C16	115.60 (16)
H7A—C7—H7B	107.3	C18—C17—H17	122.2
N4—C8—N5	104.68 (13)	C16—C17—H17	122.2
N4—C8—H8A	110.8	C17—C18—C19	122.65 (16)
N5—C8—H8A	110.8	C17—C18—H18	118.7
N4—C8—H8B	110.8	C19—C18—H18	118.7
N5—C8—H8B	110.8	C20—C19—C18	121.58 (16)
H8A—C8—H8B	108.9	C20—C19—H19	119.2
N4—C9—C14	99.64 (13)	C18—C19—H19	119.2
N4—C9—C10	117.77 (14)	C19—C20—C21	117.01 (16)
C14—C9—C10	111.14 (14)	C19—C20—H20	121.5
N4—C9—H9	109.3	C21—C20—H20	121.5
C14—C9—H9	109.3	N8—C21—C16	108.80 (14)
C10—C9—H9	109.3	N8—C21—C20	130.64 (16)
C9—C10—C11	107.98 (15)	C16—C21—C20	120.56 (15)
N3—C7—N4—C8	56.8 (4)	C8—N5—C15—N6	55.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8a···N6	0.97	2.55	2.970 (2)	106
C8—H8b···N3	0.97	2.58	2.995 (2)	106
C7—H7b···N1i	0.97	2.38	3.301 (2)	159
C15—H15b···N7ii	0.97	2.62	3.504 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7b⋯N1i	0.97	2.38	3.301 (2)	159
C15—H15b⋯N7ii	0.97	2.62	3.504 (2)	151

Symmetry codes: (i) ; (ii) .