1,1′-[Imidazolidine-1,3-diylbis(methyl­ene)]bis­(1H-benzotriazole)

Rivera, A.; Quiroga, D.; Ríos-Motta, J.; Fejfarová, K.; Dušek, M.

doi:10.1107/S1600536812000232

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o312-o313

doi:10.1107/S1600536812000232

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1,1′-[Imidazolidine-1,3-diylbis(methylene)]bis(1H-benzotriazole)

Augusto Rivera,^a ^* Diego Quiroga,^a Jaime Ríos-Motta,^a Karla Fejfarová ^b and Michal Dušek ^b

^aDepartamento de Química, Universidad Nacional de Colombia, Ciudad Universitaria, Bogotá, Colombia, and ^bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
^*Correspondence e-mail: ariverau@unal.edu.co

(Received 23 December 2011; accepted 3 January 2012; online 11 January 2012)

In the title compound, C₁₇H₁₈N₈, 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 interactions link the molecules into helical chains along the b axis. The crystal packing is further stabilized by weak C—H⋯π interactions.

Related literature

For related structures, see: Rivera et al. (2011a ,b ). 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_r = 334.4
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.073
S = 1.52
1609 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.11 e Å⁻³

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) $[-x, y+{\script{1\over 2}}, -z+2]$ ; (ii) x, y+1, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812000232/bt5768sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812000232/bt5768Isup3.cml

checkCIF report

Comment top

The anomeric effect is a stereoelectronic effect observed in various heterocyclic compounds and some acyclic structures with a great deal of importance due its implications on the molecular structure, conformational properties and reactivity of organic compounds (Zefirov & Shekhtman, 1971; Selámbaron, et al., 2001; Dabbagh, et al., 2002). Our investigations on the synthesis and structural studies of heterocyclic compounds have evidenced the occurrence of a n(N)→σ* (C—N) electron delocalization (Rivera et al., 2011a, 2011b). In this article, we discussed the crystal structure of the title compound, which can be synthetized by a three component condensation between ethylenediamine, formaldehyde and benzotriazole (Katriztky et al., 1990) or using a novel methodology involving a Mannich type reaction between the aminal cage 1,3,6,8-tetrazatricyclo[4.4.1.1^3,8]dodecane and benzotriazole (Rivera et al., 2004). By recrystallization from ethanol we obtained suitable crystals for X-rays analysis.

The molecular structure and atom-numbering scheme for (I) are shown in Fig. 1. The anomeric effect is evidenced by the C—N bond lengths, which are longer as C11—N6 [1.484 (2) Å] and shorter as N2—C11 [1.433 (2) Å] than the expected bond length of 1.469 Å (Allen et al., 1987). Moreover, this effect is confirmed by the bond angles around N2 with a Σα = 339.43 (13) which are distorted from a normal tetrahedral geometry in a five-membered ring (Hendrickson, 1961), whereas for N1 the bond lenghts and angles are within normal ranges. These results are in a good agreement with the crystal structures of related structures (Rivera et al., 2011a, 2011b).

The imidazolidine ring adopts an envelope conformation on C1 as seen in the puckering parameters Q(2) = 0.3953 (17) Å and ϕ2 = 40.3 (2) ° (Cremer & Pople, 1975), with endocyclic bond angles between 103.06 (13) ° and 106.55 (13) °. The geometry of the N—C—C—N moiety is close to the planar in a syn-periplanar conformation evidenced by the N2—C2—C3—N1 torsion angle [3.05 (17) °]. The benzotriazolylmethyl substituents are arranged trans respect the imidazolidine ring, which is preferred because the nitrogen lone pairs are oriented anti-axial to avoid repulsion electronic repulsions. The benzotriazole rings makes an angle of 38.47 (10) ° and 78.88 (10) ° with the mean plane of imidazolidine ring. The dihedral angle between the two benzotriazole rings is 71.65 (10) °. Chains of molecules in the title compound are linked along the b direction by non-classical intermolecular hydrogen bonds C17—H17···N5 interactions [2.60 Å] which link neighboring molecules. The crystal packing is further stabilized by weak C—H···π interactions.

Related literature top

For related structures, see: Rivera et al. (2011a,b). 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 top

For the originally reported synthesis, see: Rivera et al. (2004). Single crystals of the title compound (I) were grown from ethanol by recrystallization.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 (Petříček et al., 2006).

Figures top

	Fig. 1. A view of (I) with the numbering scheme.displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing of the molecules of the title compound view along b axis.

1,1'-[Imidazolidine-1,3-diylbis(methylene)]bis(1H-benzotriazole) top

Crystal data top

C₁₇H₁₈N₈	F(000) = 352
M_r = 334.4	D_x = 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

Data collection top

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 monochromator	R_int = 0.030
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.0°, θ_min = 3.1°
Rotation method data acquisition using ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −5→5
T_min = 0.378, T_max = 1	l = −17→16
10081 measured reflections

Refinement top

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	Δρ_max = 0.09 e Å⁻³
226 parameters	Δρ_min = −0.11 e Å⁻³
0 restraints

Crystal data top

C₁₇H₁₈N₈	V = 795.78 (7) Å³
M_r = 334.4	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 11.8609 (6) Å	µ = 0.74 mm⁻¹
b = 4.6429 (2) Å	T = 120 K
c = 14.4712 (8) Å	0.43 × 0.18 × 0.10 mm
β = 93.053 (4)°

Data collection top

Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	1609 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1541 reflections with I > 3σ(I)
T_min = 0.378, T_max = 1	R_int = 0.030
10081 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.52	Δρ_max = 0.09 e Å⁻³
1609 reflections	Δρ_min = −0.11 e Å⁻³
226 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₈
M_r	334.4
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	120
a, b, c (Å)	11.8609 (6), 4.6429 (2), 14.4712 (8)
β (°)	93.053 (4)
V (Å³)	795.78 (7)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.43 × 0.18 × 0.10

Data collection
Diffractometer	Agilent Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.378, 1
No. of measured, independent and observed [I > 3σ(I)] reflections	10081, 1609, 1541
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.073, 1.52
No. of reflections	1609
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.11

Computer programs: CrysAlis PRO (Agilent, 2010), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+2; (ii) x, y+1, z.

Acknowledgements

We acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work, as well as the Institutional research plan No. AVOZ10100521 of the Institute of Physics and the Praemium Academiae project of the Academy of Sciences of the Czech Republic. DQ acknowledges the Vicerrectoría Académica de la Universidad Nacional de Colombia for a fellowship.

References

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Volume 68| Part 2| February 2012| Pages o312-o313

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