1,1'-[Imidazolidine-1,3-diylbis(methyl-ene)]bis-(1H-benzotriazole).

In the title compound, C(17)H(18)N(8), the imidazolidine ring adopts an envelope conformation with the substituents at the N atoms in trans positions with respect to the central ring. The dihedral angle between the two benzotriazole rings is 71.65 (10)°. In the crystal, non-classical C-H⋯N inter-actions link the mol-ecules into helical chains along the b axis. The crystal packing is further stabilized by weak C-H⋯π inter-actions.

Related literature

For related structures, see: Rivera et al. (2011 ▶). For the synthesis of the title compound, see: Rivera et al. (2004 ▶); Katriztky et al. (1990 ▶). For ring conformations, see Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the anomeric effect, see: Dabbagh et al. (2002 ▶); Selámbaron et al. (2001 ▶); Zefirov & Shekhtman (1971 ▶); Hendrickson (1961 ▶).

Experimental

Crystal data

C17H18N8

M = 334.4

Monoclinic,

a = 11.8609 (6) Å

b = 4.6429 (2) Å

c = 14.4712 (8) Å

β = 93.053 (4)°

V = 795.78 (7) Å3

Z = 2

Cu Kα radiation

μ = 0.74 mm−1

T = 120 K

0.43 × 0.18 × 0.10 mm

Data collection

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.378, T max = 1

10081 measured reflections

1609 independent reflections

1541 reflections with I > 3σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.073

S = 1.52

1609 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.09 e Å−3

Δρmin = −0.11 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000232/bt5768sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000232/bt5768Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000232/bt5768Isup3.cml

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

C17H18N8	F(000) = 352
Mr = 334.4	Dx = 1.395 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2yb	Cell parameters from 7090 reflections
a = 11.8609 (6) Å	θ = 3.1–66.9°
b = 4.6429 (2) Å	µ = 0.74 mm−1
c = 14.4712 (8) Å	T = 120 K
β = 93.053 (4)°	Prism, colourless
V = 795.78 (7) Å3	0.43 × 0.18 × 0.10 mm
Z = 2

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1609 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1541 reflections with I > 3σ(I)
mirror	Rint = 0.030
Detector resolution: 10.3784 pixels mm-1	θmax = 67.0°, θmin = 3.1°
Rotation method data acquisition using ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −5→5
Tmin = 0.378, Tmax = 1	l = −17→16
10081 measured reflections

Refinement on F2	73 constraints
R[F2 > 2σ(F2)] = 0.027	H-atom parameters constrained
wR(F2) = 0.073	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
S = 1.52	(Δ/σ)max = 0.005
1609 reflections	Δρmax = 0.09 e Å−3
226 parameters	Δρmin = −0.11 e Å−3
0 restraints

Experimental. CrysAlisPro (Agilent, 2010) 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	0.21591 (11)	0.2699 (3)	0.93068 (9)	0.0235 (4)
N2	0.26794 (11)	0.5272 (3)	1.06164 (10)	0.0238 (4)
N3	0.09989 (11)	0.3594 (3)	0.79499 (9)	0.0235 (4)
N4	−0.01384 (12)	0.4004 (4)	0.78915 (11)	0.0290 (4)
N5	−0.05795 (11)	0.2425 (4)	0.72197 (10)	0.0298 (5)
N6	0.40908 (11)	0.4060 (3)	1.18741 (10)	0.0239 (4)
N7	0.50606 (11)	0.2991 (4)	1.15561 (10)	0.0280 (4)
N8	0.54874 (11)	0.1110 (4)	1.21481 (10)	0.0279 (4)
C1	0.31519 (14)	0.3661 (4)	0.98560 (11)	0.0264 (5)
C2	0.17294 (13)	0.3532 (4)	1.09029 (11)	0.0248 (5)
C3	0.13569 (13)	0.1890 (4)	1.00110 (11)	0.0239 (5)
C4	0.17205 (15)	0.4928 (4)	0.86759 (12)	0.0263 (5)
C5	0.12961 (13)	0.1659 (4)	0.73030 (11)	0.0215 (5)
C6	0.02769 (13)	0.0916 (4)	0.68333 (12)	0.0253 (5)
C7	0.02635 (16)	−0.1107 (4)	0.61123 (12)	0.0314 (5)
C8	0.12773 (17)	−0.2263 (5)	0.58977 (12)	0.0354 (6)
C9	0.23000 (15)	−0.1486 (5)	0.63788 (12)	0.0308 (5)
C10	0.23362 (14)	0.0484 (4)	0.70895 (11)	0.0251 (5)
C11	0.34550 (15)	0.6304 (4)	1.13345 (12)	0.0286 (5)
C12	0.38817 (13)	0.2843 (4)	1.27059 (11)	0.0228 (5)
C13	0.47863 (13)	0.0943 (4)	1.28781 (12)	0.0232 (5)
C14	0.48715 (14)	−0.0715 (4)	1.36880 (12)	0.0270 (5)
C15	0.40331 (15)	−0.0378 (4)	1.42939 (13)	0.0311 (5)
C16	0.31195 (15)	0.1530 (5)	1.41080 (13)	0.0329 (6)
C17	0.30163 (14)	0.3172 (4)	1.33186 (12)	0.0293 (5)
H1a	0.358632	0.493853	0.949314	0.0316*
H1b	0.355874	0.201865	1.010035	0.0316*
H2a	0.113022	0.477804	1.107635	0.0298*
H2b	0.199161	0.21839	1.136922	0.0298*
H3a	0.140331	−0.014517	1.012342	0.0287*
H3b	0.060918	0.24844	0.980747	0.0287*
H4a	0.128774	0.628658	0.901023	0.0316*
H4b	0.233758	0.58913	0.840354	0.0316*
H7	−0.042768	−0.165557	0.578371	0.0376*
H8	0.129465	−0.364408	0.540509	0.0424*
H9	0.299061	−0.236079	0.620438	0.037*
H10	0.302981	0.101822	0.741735	0.0302*
H11a	0.30616	0.75146	1.174811	0.0343*
H11b	0.397607	0.762446	1.107664	0.0343*
H14	0.54877	−0.2024	1.381195	0.0325*
H15	0.406631	−0.146438	1.485921	0.0373*
H16	0.254861	0.1683	1.45514	0.0395*
H17	0.239268	0.445844	1.319532	0.0351*

	U11	U22	U33	U12	U13	U23
N1	0.0240 (6)	0.0259 (8)	0.0205 (7)	−0.0003 (6)	−0.0004 (5)	0.0012 (6)
N2	0.0261 (7)	0.0225 (7)	0.0223 (7)	−0.0021 (6)	−0.0037 (5)	0.0009 (6)
N3	0.0221 (6)	0.0253 (7)	0.0229 (7)	0.0011 (6)	−0.0008 (5)	0.0020 (6)
N4	0.0230 (7)	0.0315 (8)	0.0326 (8)	0.0042 (7)	0.0022 (6)	0.0053 (7)
N5	0.0218 (7)	0.0346 (9)	0.0325 (8)	−0.0010 (6)	−0.0027 (5)	0.0075 (7)
N6	0.0235 (6)	0.0241 (8)	0.0235 (7)	−0.0008 (6)	−0.0032 (5)	−0.0013 (6)
N7	0.0227 (6)	0.0338 (9)	0.0269 (7)	−0.0032 (6)	−0.0025 (5)	−0.0021 (7)
N8	0.0221 (7)	0.0336 (9)	0.0275 (7)	0.0006 (6)	−0.0023 (5)	−0.0019 (7)
C1	0.0233 (7)	0.0334 (10)	0.0224 (8)	−0.0017 (8)	0.0009 (6)	0.0024 (8)
C2	0.0212 (7)	0.0296 (9)	0.0236 (8)	0.0009 (7)	0.0008 (6)	−0.0008 (7)
C3	0.0233 (8)	0.0239 (9)	0.0243 (8)	−0.0025 (7)	−0.0007 (6)	0.0003 (7)
C4	0.0323 (8)	0.0244 (9)	0.0219 (8)	−0.0026 (8)	−0.0032 (6)	−0.0010 (7)
C5	0.0234 (7)	0.0221 (9)	0.0187 (7)	−0.0006 (7)	−0.0008 (6)	0.0035 (7)
C6	0.0240 (8)	0.0260 (9)	0.0255 (8)	−0.0022 (7)	−0.0033 (6)	0.0080 (7)
C7	0.0360 (9)	0.0301 (10)	0.0267 (9)	−0.0058 (8)	−0.0098 (7)	0.0031 (8)
C8	0.0514 (11)	0.0314 (10)	0.0228 (8)	−0.0009 (9)	−0.0021 (7)	−0.0015 (8)
C9	0.0332 (8)	0.0330 (11)	0.0264 (8)	0.0063 (8)	0.0038 (6)	0.0011 (8)
C10	0.0229 (8)	0.0291 (10)	0.0235 (8)	−0.0004 (7)	0.0009 (6)	0.0029 (7)
C11	0.0348 (9)	0.0208 (9)	0.0288 (9)	−0.0039 (8)	−0.0109 (7)	0.0012 (8)
C12	0.0224 (7)	0.0225 (9)	0.0228 (8)	−0.0029 (7)	−0.0062 (6)	−0.0028 (7)
C13	0.0193 (7)	0.0246 (9)	0.0253 (8)	−0.0022 (7)	−0.0032 (6)	−0.0039 (7)
C14	0.0262 (8)	0.0241 (9)	0.0299 (9)	0.0014 (7)	−0.0066 (6)	0.0000 (7)
C15	0.0322 (9)	0.0317 (11)	0.0289 (9)	−0.0030 (8)	−0.0028 (7)	0.0043 (8)
C16	0.0292 (8)	0.0394 (11)	0.0303 (9)	−0.0009 (8)	0.0039 (7)	−0.0004 (9)
C17	0.0238 (8)	0.0336 (11)	0.0302 (9)	0.0041 (8)	−0.0013 (6)	−0.0026 (8)

N1—C1	1.455 (2)	C4—H4b	0.96
N1—C3	1.479 (2)	C5—C6	1.398 (2)
N1—C4	1.458 (2)	C5—C10	1.398 (2)
N2—C1	1.466 (2)	C6—C7	1.403 (3)
N2—C2	1.464 (2)	C7—C8	1.368 (3)
N2—C11	1.433 (2)	C7—H7	0.96
N3—N4	1.3604 (19)	C8—C9	1.413 (3)
N3—C4	1.458 (2)	C8—H8	0.96
N3—C5	1.357 (2)	C9—C10	1.376 (3)
N4—N5	1.305 (2)	C9—H9	0.96
N5—C6	1.377 (2)	C10—H10	0.96
N6—N7	1.355 (2)	C11—H11a	0.96
N6—C11	1.484 (2)	C11—H11b	0.96
N6—C12	1.364 (2)	C12—C13	1.401 (2)
N7—N8	1.307 (2)	C12—C17	1.400 (2)
N8—C13	1.381 (2)	C13—C14	1.402 (2)
C1—H1a	0.96	C14—C15	1.369 (3)
C1—H1b	0.96	C14—H14	0.96
C2—C3	1.543 (2)	C15—C16	1.414 (3)
C2—H2a	0.96	C15—H15	0.96
C2—H2b	0.96	C16—C17	1.373 (3)
C3—H3a	0.96	C16—H16	0.96
C3—H3b	0.96	C17—H17	0.96
C4—H4a	0.96
C1—N1—C3	103.48 (12)	N3—C5—C10	132.45 (15)
C1—N1—C4	112.04 (14)	C6—C5—C10	123.13 (15)
C3—N1—C4	112.98 (13)	N5—C6—C5	108.33 (15)
C1—N2—C2	105.19 (14)	N5—C6—C7	131.54 (15)
C1—N2—C11	117.30 (13)	C5—C6—C7	120.12 (16)
C2—N2—C11	116.94 (13)	C6—C7—C8	117.14 (16)
N4—N3—C4	121.83 (14)	C6—C7—H7	121.4291
N4—N3—C5	110.05 (13)	C8—C7—H7	121.4287
C4—N3—C5	127.90 (14)	C7—C8—C9	122.02 (18)
N3—N4—N5	108.94 (14)	C7—C8—H8	118.9882
N4—N5—C6	108.26 (13)	C9—C8—H8	118.9897
N7—N6—C11	119.68 (14)	C8—C9—C10	122.01 (17)
N7—N6—C12	110.21 (14)	C8—C9—H9	118.9967
C11—N6—C12	130.08 (14)	C10—C9—H9	118.9971
N6—N7—N8	109.17 (13)	C5—C10—C9	115.58 (15)
N7—N8—C13	108.11 (14)	C5—C10—H10	122.2124
N1—C1—N2	103.65 (13)	C9—C10—H10	122.2126
N1—C1—H1a	109.4707	N2—C11—N6	115.81 (15)
N1—C1—H1b	109.4711	N2—C11—H11a	109.4718
N2—C1—H1a	109.4712	N2—C11—H11b	109.4704
N2—C1—H1b	109.4715	N6—C11—H11a	109.4709
H1a—C1—H1b	114.7236	N6—C11—H11b	109.4712
N2—C2—C3	103.06 (13)	H11a—C11—H11b	102.2888
N2—C2—H2a	109.4714	N6—C12—C13	104.13 (14)
N2—C2—H2b	109.4715	N6—C12—C17	133.44 (16)
C3—C2—H2a	109.4717	C13—C12—C17	122.43 (16)
C3—C2—H2b	109.4711	N8—C13—C12	108.38 (15)
H2a—C2—H2b	115.2	N8—C13—C14	130.61 (16)
N1—C3—C2	106.55 (13)	C12—C13—C14	121.01 (15)
N1—C3—H3a	109.4715	C13—C14—C15	116.76 (16)
N1—C3—H3b	109.4715	C13—C14—H14	121.6205
C2—C3—H3a	109.4712	C15—C14—H14	121.6212
C2—C3—H3b	109.4712	C14—C15—C16	121.66 (17)
H3a—C3—H3b	112.2427	C14—C15—H15	119.1684
N1—C4—N3	109.01 (15)	C16—C15—H15	119.1674
N1—C4—H4a	109.4712	C15—C16—C17	122.64 (17)
N1—C4—H4b	109.4703	C15—C16—H16	118.6785
N3—C4—H4a	109.4717	C17—C16—H16	118.6776
N3—C4—H4b	109.4721	C12—C17—C16	115.49 (16)
H4a—C4—H4b	109.9289	C12—C17—H17	122.2546
N3—C5—C6	104.42 (14)	C16—C17—H17	122.2552
N2—C2—C3—N1	3.05 (17)

Cg3 is the centroid of the N6/N7/N8/C13/C12 aromatic ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···N5i	0.96	2.60	3.552 (2)	173
C11—H11b···Cg3ii	0.96	2.86	3.394 (2)	116

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the N6/N7/N8/C13/C12 aromatic ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯N5i	0.96	2.60	3.552 (2)	173
C11—H11b⋯Cg3ii	0.96	2.86	3.394 (2)	116

Symmetry codes: (i) ; (ii) .