1,3-Bis[(1H-benzotriazol-1-yl)meth-yl]-2,3-dihydro-1H-benzimidazole.

In the title compound, C(21)H(18)N(8), the two (benzotriazol-1-yl)methyl groups are located in an anti position with respect to the benzimidazoline moiety. The dihedral angles between the benzotriazole ring systems and the central benzimidazoline moiety are 57.03 (4) and 81.01 (3)°. The crystal packing is stabilized by two C-H⋯π inter-actions.

Related literature

For chemical background to the synthesis of the title compound, see: Katritzky et al. (1990 ▶); Rivera et al. (2004 ▶). For related structures, see: Wang et al. (2008 ▶); Kuhl et al. (2008 ▶); Rivera et al. (2010 ▶). For the tautomerism of benzotriazole, see: Elguero et al. (2000 ▶).

Experimental

Crystal data

C21H18N8

M = 382.4

Monoclinic,

a = 9.0037 (2) Å

b = 11.5733 (3) Å

c = 18.0167 (4) Å

β = 103.056 (2)°

V = 1828.85 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.72 mm−1

T = 120 K

0.33 × 0.17 × 0.06 mm

Data collection

Oxford diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.139, T max = 1

27458 measured reflections

3269 independent reflections

2644 reflections with I > 3σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.45

3269 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2007 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010701/bt5499sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010701/bt5499Isup2.hkl

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

C21H18N8	F(000) = 800
Mr = 382.4	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 11617 reflections
a = 9.0037 (2) Å	θ = 3.8–67.1°
b = 11.5733 (3) Å	µ = 0.72 mm−1
c = 18.0167 (4) Å	T = 120 K
β = 103.056 (2)°	Plate, colourless
V = 1828.85 (8) Å3	0.33 × 0.17 × 0.06 mm
Z = 4

Oxford diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	3269 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2644 reflections with I > 3σ(I)
mirror	Rint = 0.040
Detector resolution: 10.3784 pixels mm-1	θmax = 67.2°, θmin = 4.6°
Rotation method data acquisition using ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
Tmin = 0.139, Tmax = 1	l = −21→21
27458 measured reflections

Refinement on F2	72 constraints
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.091	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 1.45	(Δ/σ)max = 0.007
3269 reflections	Δρmax = 0.13 e Å−3
262 parameters	Δρmin = −0.13 e Å−3
0 restraints

Experimental. CrysAlisPro, Oxford Diffraction (2009), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
N1	0.53621 (12)	0.20581 (9)	0.71929 (6)	0.0295 (4)
N2	0.28286 (12)	0.23894 (9)	0.69788 (7)	0.0335 (4)
N3	0.05847 (12)	0.28228 (9)	0.74331 (6)	0.0285 (3)
N4	0.00392 (13)	0.39061 (10)	0.72735 (7)	0.0356 (4)
N5	−0.04882 (14)	0.42890 (10)	0.78456 (7)	0.0388 (4)
N6	0.69451 (12)	0.08507 (9)	0.65658 (6)	0.0294 (3)
N7	0.78450 (13)	0.13645 (10)	0.61473 (7)	0.0371 (4)
N8	0.78890 (14)	0.07188 (11)	0.55626 (7)	0.0398 (4)
C1	0.39297 (15)	0.14738 (12)	0.72079 (8)	0.0313 (4)
C2	0.34562 (15)	0.32489 (11)	0.66049 (7)	0.0273 (4)
C3	0.50269 (15)	0.30412 (11)	0.67269 (7)	0.0268 (4)
C4	0.59574 (15)	0.37697 (11)	0.64336 (7)	0.0310 (4)
C5	0.52849 (16)	0.47226 (11)	0.60077 (8)	0.0330 (4)
C6	0.37375 (16)	0.49275 (12)	0.58887 (8)	0.0331 (4)
C7	0.27925 (16)	0.41919 (11)	0.61955 (8)	0.0313 (4)
C8	0.12278 (15)	0.21954 (11)	0.68743 (8)	0.0299 (4)
C9	0.04208 (14)	0.24901 (11)	0.81371 (7)	0.0280 (4)
C10	−0.02855 (15)	0.34352 (12)	0.83937 (8)	0.0338 (4)
C11	−0.07110 (17)	0.33944 (14)	0.90961 (9)	0.0422 (5)
C12	−0.03998 (18)	0.23970 (15)	0.95043 (9)	0.0460 (6)
C13	0.03345 (18)	0.14500 (14)	0.92440 (8)	0.0416 (5)
C14	0.07602 (15)	0.14743 (12)	0.85558 (8)	0.0330 (4)
C15	0.67410 (15)	0.14109 (12)	0.72642 (8)	0.0318 (4)
C16	0.63898 (14)	−0.01708 (11)	0.62348 (7)	0.0279 (4)
C17	0.69984 (15)	−0.02422 (12)	0.55896 (8)	0.0325 (4)
C18	0.66863 (18)	−0.11979 (13)	0.51014 (8)	0.0402 (5)
C19	0.57612 (18)	−0.20363 (13)	0.52823 (8)	0.0413 (5)
C20	0.51487 (17)	−0.19509 (12)	0.59347 (8)	0.0390 (5)
C21	0.54493 (15)	−0.10265 (11)	0.64245 (8)	0.0322 (4)
H1a	0.37474	0.087187	0.683165	0.0376*
H1b	0.393574	0.124273	0.772035	0.0376*
H4	0.703349	0.362945	0.651809	0.0372*
H5	0.590948	0.524185	0.579504	0.0396*
H6	0.330247	0.558337	0.559148	0.0397*
H7	0.172033	0.434108	0.61224	0.0376*
H8a	0.103977	0.138348	0.691226	0.0358*
H8b	0.071757	0.242837	0.636967	0.0358*
H11	−0.119754	0.403749	0.928018	0.0507*
H12	−0.068878	0.233577	0.998411	0.0552*
H13	0.054267	0.077025	0.955556	0.0499*
H14	0.125822	0.083288	0.837671	0.0396*
H15a	0.68079	0.084238	0.765834	0.0381*
H15b	0.759932	0.190138	0.74614	0.0381*
H18	0.71056	−0.126041	0.465815	0.0483*
H19	0.552197	−0.269984	0.495748	0.0496*
H20	0.450035	−0.255859	0.604024	0.0468*
H21	0.503676	−0.097288	0.687027	0.0386*

	U11	U22	U33	U12	U13	U23
N1	0.0281 (6)	0.0275 (6)	0.0335 (6)	0.0015 (4)	0.0082 (5)	0.0025 (5)
N2	0.0286 (6)	0.0297 (6)	0.0445 (7)	0.0023 (5)	0.0133 (5)	0.0086 (5)
N3	0.0274 (5)	0.0258 (6)	0.0323 (6)	−0.0002 (4)	0.0070 (5)	−0.0002 (5)
N4	0.0364 (6)	0.0281 (6)	0.0420 (7)	0.0039 (5)	0.0082 (5)	0.0003 (5)
N5	0.0383 (6)	0.0353 (7)	0.0424 (7)	0.0048 (5)	0.0085 (5)	−0.0050 (5)
N6	0.0259 (5)	0.0277 (6)	0.0349 (6)	−0.0002 (4)	0.0073 (5)	0.0008 (5)
N7	0.0297 (6)	0.0363 (6)	0.0483 (7)	−0.0006 (5)	0.0153 (5)	0.0032 (5)
N8	0.0384 (7)	0.0396 (7)	0.0457 (7)	0.0049 (5)	0.0187 (6)	0.0056 (6)
C1	0.0304 (7)	0.0295 (7)	0.0342 (7)	0.0005 (5)	0.0074 (6)	0.0027 (6)
C2	0.0310 (7)	0.0255 (6)	0.0260 (6)	−0.0034 (5)	0.0077 (5)	−0.0031 (5)
C3	0.0307 (7)	0.0249 (6)	0.0246 (6)	−0.0009 (5)	0.0060 (5)	−0.0045 (5)
C4	0.0297 (7)	0.0303 (7)	0.0329 (7)	−0.0054 (6)	0.0069 (6)	−0.0047 (6)
C5	0.0395 (8)	0.0288 (7)	0.0312 (7)	−0.0093 (6)	0.0091 (6)	−0.0025 (5)
C6	0.0429 (8)	0.0252 (7)	0.0303 (7)	−0.0023 (6)	0.0063 (6)	0.0007 (5)
C7	0.0314 (7)	0.0291 (7)	0.0325 (7)	0.0002 (6)	0.0050 (6)	−0.0009 (5)
C8	0.0297 (7)	0.0293 (7)	0.0319 (7)	−0.0022 (5)	0.0098 (6)	−0.0021 (5)
C9	0.0221 (6)	0.0322 (7)	0.0289 (7)	−0.0054 (5)	0.0040 (5)	−0.0043 (5)
C10	0.0281 (7)	0.0354 (8)	0.0373 (8)	−0.0036 (6)	0.0060 (6)	−0.0084 (6)
C11	0.0368 (8)	0.0518 (10)	0.0393 (8)	−0.0049 (7)	0.0110 (6)	−0.0134 (7)
C12	0.0442 (9)	0.0632 (11)	0.0324 (8)	−0.0140 (8)	0.0127 (7)	−0.0093 (7)
C13	0.0446 (8)	0.0452 (9)	0.0328 (7)	−0.0131 (7)	0.0043 (6)	0.0017 (6)
C14	0.0315 (7)	0.0322 (7)	0.0337 (7)	−0.0052 (6)	0.0037 (6)	−0.0016 (6)
C15	0.0285 (7)	0.0337 (7)	0.0309 (7)	0.0008 (5)	0.0020 (5)	−0.0018 (6)
C16	0.0256 (6)	0.0279 (7)	0.0286 (6)	0.0046 (5)	0.0023 (5)	0.0026 (5)
C17	0.0316 (7)	0.0328 (7)	0.0334 (7)	0.0082 (6)	0.0081 (6)	0.0056 (6)
C18	0.0484 (9)	0.0413 (8)	0.0305 (7)	0.0142 (7)	0.0079 (6)	0.0009 (6)
C19	0.0519 (9)	0.0317 (8)	0.0351 (8)	0.0080 (7)	−0.0010 (7)	−0.0050 (6)
C20	0.0423 (8)	0.0276 (7)	0.0434 (9)	0.0004 (6)	0.0021 (7)	0.0018 (6)
C21	0.0345 (7)	0.0282 (7)	0.0334 (7)	0.0022 (6)	0.0067 (6)	0.0030 (6)

N1—C1	1.4619 (18)	C6—H6	0.96
N1—C3	1.4057 (16)	C7—H7	0.96
N1—C15	1.4307 (17)	C8—H8a	0.96
N2—C1	1.4461 (17)	C8—H8b	0.96
N2—C2	1.3908 (18)	C9—C10	1.395 (2)
N2—C8	1.4286 (17)	C9—C14	1.3931 (18)
N3—N4	1.3535 (15)	C10—C11	1.403 (2)
N3—C8	1.4626 (19)	C11—C12	1.363 (2)
N3—C9	1.3651 (18)	C11—H11	0.96
N4—N5	1.3058 (19)	C12—C13	1.414 (2)
N5—C10	1.3797 (19)	C12—H12	0.96
N6—N7	1.3618 (18)	C13—C14	1.378 (2)
N6—C15	1.4635 (18)	C13—H13	0.96
N6—C16	1.3668 (16)	C14—H14	0.96
N7—N8	1.2994 (18)	C15—H15a	0.96
N8—C17	1.3784 (19)	C15—H15b	0.96
C1—H1a	0.96	C16—C17	1.395 (2)
C1—H1b	0.96	C16—C21	1.3948 (19)
C2—C3	1.4020 (18)	C17—C18	1.402 (2)
C2—C7	1.3759 (17)	C18—C19	1.365 (2)
C3—C4	1.376 (2)	C18—H18	0.96
C4—C5	1.4006 (18)	C19—C20	1.410 (2)
C4—H4	0.96	C19—H19	0.96
C5—C6	1.381 (2)	C20—C21	1.3743 (19)
C5—H5	0.96	C20—H20	0.96
C6—C7	1.402 (2)	C21—H21	0.96
C1—N1—C3	108.31 (10)	N3—C8—H8b	109.4707
C1—N1—C15	120.50 (11)	H8a—C8—H8b	106.7384
C3—N1—C15	122.84 (12)	N3—C9—C10	103.88 (11)
C1—N2—C2	109.58 (11)	N3—C9—C14	133.21 (13)
C1—N2—C8	121.91 (11)	C10—C9—C14	122.87 (13)
C2—N2—C8	123.83 (10)	N5—C10—C9	108.70 (13)
N4—N3—C8	119.65 (11)	N5—C10—C11	130.59 (14)
N4—N3—C9	110.39 (11)	C9—C10—C11	120.67 (13)
C8—N3—C9	129.96 (11)	C10—C11—C12	116.76 (15)
N3—N4—N5	109.02 (11)	C10—C11—H11	121.6181
N4—N5—C10	108.00 (12)	C12—C11—H11	121.6189
N7—N6—C15	119.24 (10)	C11—C12—C13	122.14 (16)
N7—N6—C16	109.93 (11)	C11—C12—H12	118.9315
C15—N6—C16	130.82 (12)	C13—C12—H12	118.9322
N6—N7—N8	109.19 (11)	C12—C13—C14	121.91 (14)
N7—N8—C17	108.11 (13)	C12—C13—H13	119.0442
N1—C1—N2	101.92 (10)	C14—C13—H13	119.044
N1—C1—H1a	109.4711	C9—C14—C13	115.65 (13)
N1—C1—H1b	109.4711	C9—C14—H14	122.176
N2—C1—H1a	109.4717	C13—C14—H14	122.1781
N2—C1—H1b	109.4706	N1—C15—N6	115.45 (10)
H1a—C1—H1b	116.0962	N1—C15—H15a	109.4716
N2—C2—C3	107.89 (10)	N1—C15—H15b	109.4715
N2—C2—C7	130.71 (12)	N6—C15—H15a	109.4709
C3—C2—C7	121.37 (13)	N6—C15—H15b	109.4707
N1—C3—C2	107.78 (11)	H15a—C15—H15b	102.7515
N1—C3—C4	131.17 (12)	N6—C16—C17	103.94 (12)
C2—C3—C4	121.00 (11)	N6—C16—C21	133.61 (13)
C3—C4—C5	117.88 (13)	C17—C16—C21	122.45 (12)
C3—C4—H4	121.0592	N8—C17—C16	108.83 (12)
C5—C4—H4	121.0603	N8—C17—C18	130.57 (14)
C4—C5—C6	121.08 (13)	C16—C17—C18	120.59 (13)
C4—C5—H5	119.4594	C17—C18—C19	117.23 (15)
C6—C5—H5	119.4597	C17—C18—H18	121.3823
C5—C6—C7	121.00 (12)	C19—C18—H18	121.3839
C5—C6—H6	119.499	C18—C19—C20	121.59 (14)
C7—C6—H6	119.4995	C18—C19—H19	119.2076
C2—C7—C6	117.65 (13)	C20—C19—H19	119.2074
C2—C7—H7	121.1743	C19—C20—C21	122.17 (14)
C6—C7—H7	121.1739	C19—C20—H20	118.9165
N2—C8—N3	112.07 (10)	C21—C20—H20	118.9176
N2—C8—H8a	109.4717	C16—C21—C20	115.97 (14)
N2—C8—H8b	109.4715	C16—C21—H21	122.0168
N3—C8—H8a	109.4707	C20—C21—H21	122.0158
C3—N1—C1—N2	−20.63 (13)	N7—N8—C17—C16	−0.40 (16)
C15—N1—C1—N2	−169.70 (11)	N7—N8—C17—C18	−179.17 (15)
C1—N1—C3—C2	14.16 (14)	N2—C2—C3—N1	−1.19 (14)
C1—N1—C3—C4	−168.50 (13)	N2—C2—C3—C4	−178.85 (12)
C15—N1—C3—C2	162.35 (11)	C7—C2—C3—N1	176.99 (12)
C15—N1—C3—C4	−20.3 (2)	C7—C2—C3—C4	−0.67 (19)
C1—N1—C15—N6	80.80 (15)	N2—C2—C7—C6	179.09 (13)
C3—N1—C15—N6	−63.69 (16)	C3—C2—C7—C6	1.39 (19)
C2—N2—C1—N1	20.13 (14)	N1—C3—C4—C5	−177.23 (13)
C8—N2—C1—N1	176.70 (12)	C2—C3—C4—C5	−0.19 (19)
C1—N2—C2—C3	−12.47 (14)	C3—C4—C5—C6	0.28 (19)
C1—N2—C2—C7	169.58 (14)	C4—C5—C6—C7	0.5 (2)
C8—N2—C2—C3	−168.51 (12)	C5—C6—C7—C2	−1.3 (2)
C8—N2—C2—C7	13.6 (2)	N3—C9—C10—N5	−0.99 (15)
C1—N2—C8—N3	114.09 (13)	N3—C9—C10—C11	176.99 (13)
C2—N2—C8—N3	−92.71 (15)	C14—C9—C10—N5	−178.84 (13)
C8—N3—N4—N5	179.34 (11)	C14—C9—C10—C11	−0.9 (2)
C9—N3—N4—N5	−0.58 (15)	N3—C9—C14—C13	−176.33 (14)
N4—N3—C8—N2	90.24 (14)	C10—C9—C14—C13	0.8 (2)
C9—N3—C8—N2	−89.85 (16)	N5—C10—C11—C12	177.47 (15)
N4—N3—C9—C10	0.95 (14)	C9—C10—C11—C12	0.0 (2)
N4—N3—C9—C14	178.48 (14)	C10—C11—C12—C13	0.9 (2)
C8—N3—C9—C10	−178.96 (13)	C11—C12—C13—C14	−0.9 (3)
C8—N3—C9—C14	−1.4 (2)	C12—C13—C14—C9	0.1 (2)
N3—N4—N5—C10	−0.08 (16)	N6—C16—C17—N8	0.44 (15)
N4—N5—C10—C9	0.69 (16)	N6—C16—C17—C18	179.36 (13)
N4—N5—C10—C11	−177.02 (15)	C21—C16—C17—N8	−179.23 (12)
C15—N6—N7—N8	178.98 (11)	C21—C16—C17—C18	−0.3 (2)
C16—N6—N7—N8	0.10 (15)	N6—C16—C21—C20	−179.76 (14)
N7—N6—C15—N1	99.09 (14)	C17—C16—C21—C20	−0.2 (2)
C16—N6—C15—N1	−82.29 (17)	N8—C17—C18—C19	179.21 (15)
N7—N6—C16—C17	−0.33 (14)	C16—C17—C18—C19	0.6 (2)
N7—N6—C16—C21	179.29 (14)	C17—C18—C19—C20	−0.3 (2)
C15—N6—C16—C17	−179.05 (13)	C18—C19—C20—C21	−0.2 (2)
C15—N6—C16—C21	0.6 (2)	C19—C20—C21—C16	0.5 (2)
N6—N7—N8—C17	0.19 (15)

Cg2 is the centroid of the N3–N5/C9/C10 ring and Cg4 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···Cg2i	0.96	2.76	3.7131 (15)	172
C19—H19···Cg4ii	0.96	2.74	3.6277 (15)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the N3–N5/C9/C10 ring and Cg4 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯Cg2i	0.96	2.76	3.7131 (15)	172
C19—H19⋯Cg4ii	0.96	2.74	3.6277 (15)	154

Symmetry codes: (i) ; (ii) .