N-(Pyridin-2-ylmeth­yl)pyridin-2-amine

Moon, S.-H.; Kim, T.H.; Park, K.-M.

doi:10.1107/S1600536811016874

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1355

doi:10.1107/S1600536811016874

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N-(Pyridin-2-ylmethyl)pyridin-2-amine

Suk-Hee Moon,^a Tae Ho Kim ^b ^* and Ki-Min Park ^b ^*

^aDepartment of Food & Nutrition, Kyungnam College of Information and Technology, Busan 616-701, Republic of Korea, and ^bDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
^*Correspondence e-mail: thkim@gnu.ac.kr, kmpark@gnu.ac.kr

(Received 3 May 2011; accepted 4 May 2011; online 7 May 2011)

The title compound, C₁₁H₁₁N₃, crystallizes with two molecules (A and B) in the asymmetric unit. The geometries of both molecules are very similar, with the exception of the torsion angles of the inter-ring chains; the values for C—N—C—C are 67.4 (5) and −69.3 (5)° for molecules A and B, respectively. The dihedral angles between the pyridyl ring planes are 84.0 (2) and 83.2 (2)° for molecules A and B, respectively. In the crystal, weak intermolecular N—H⋯N hydrogen bonds and C—H⋯π interactions contribute to the stabilization of the packing.

Related literature

For details of the synthesis, see: Foxon et al. (2002 ). For the crystal structures of Cu complexes of the title compound, see: Lee et al. (2008 ).

Experimental

Crystal data

C₁₁H₁₁N₃
M_r = 185.23
Orthorhombic, P c a 2₁
a = 14.5434 (14) Å
b = 5.8198 (6) Å
c = 23.045 (2) Å
V = 1950.5 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.45 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer
11034 measured reflections
2182 independent reflections
1814 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.124
S = 1.10
2182 reflections
253 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N4/C12–C16, N2/C7–C11 and N5/C18–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N4	0.89	2.14	3.019 (5)	172
N6—H6N⋯N1	0.93	2.10	3.012 (5)	168
C1—H1⋯Cg1ⁱ	0.95	2.77	3.53	137
C3—H3⋯Cg2ⁱⁱ	0.95	2.85	3.69	147
C14—H14⋯Cg3ⁱⁱⁱ	0.95	2.65	3.51	149
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+2, z]$ ; (ii) $[x+{\script{1\over 2}}, -y+1, z]$ ; (iii) $[x-{\script{1\over 2}}, -y+2, z]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016874/wn2432sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016874/wn2432Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016874/wn2432Isup3.cml

checkCIF report

Comment top

The title compound was prepared for use as a multidentate ligand in the formation of metallosupramolecules according to a published literature procedure (Foxon et al., 2002). The crystal structures of Cu complexes of the title compound have already been reported (Lee et al., 2008). However the crystal structure of the free form has not yet been reported.

The title compound (Scheme, Fig. 1) crystallized in the non-centrosymmetric space group Pca2₁. The asymmetric unit contains two crystallographically independent molecules (A and B). The geometries of both molecules are very similar, with the exception of the torsion angles of the inter-ring chains; the value for C5—N3—C6—C7 is 67.4 (5) ° and for C16—N6—C17—C18 is -69.3 (5) °. The dihedral angles between the pyridyl ring planes are 84.0 (2)° and 83.2 (2) ° for molecules A and B, respectively.

In the crystal structure, the amine groups of both molecules are involved in pair-wise intermolecular N—H···N interactions, leading to the formation of dimers (Table 1, Fig. 1, Fig. 2). Weak intermolecular C—H···π interactions are also present (Fig. 2). These intermolecular interactions contribute to the stabilization of the packing.

Related literature top

For details of the synthesis, see: Foxon et al. (2002). For the crystal structures of Cu complexes of the title compound, see: Lee et al. (2008).

Experimental top

The title compound was synthesized according to a literature procedure (Foxon et al., 2002). Slow evaporation of a solution in CH₃OH gave single crystals suitable for X-ray analysis.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the asymmetric unit of the title compound, showing displacement ellipsoids drawn at the 50% probability level. Dashed lines indicate hydrogen bonds

Fig. 2. Crystal packing of the title compound with intermolecular N—H···N hydrogen bonds and C—H···π interactions shown as dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity. Cg1 Cg2 and Cg3 are the centroids of the N4/C12–C16, N2/C7–C11 and N5/C18–C22 rings, respectively. (Symmetry codes: i) x + 1/2, -y + 2, z; ii) x + 1/2, -y + 1, z; iii) x - 1/2, -y + 2, z; iv) x - 1/2, -y + 1, z)

N-(Pyridin-2-ylmethyl)pyridin-2-amine top

Crystal data top

C₁₁H₁₁N₃	F(000) = 784
M_r = 185.23	D_x = 1.262 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4097 reflections
a = 14.5434 (14) Å	θ = 2.3–27.2°
b = 5.8198 (6) Å	µ = 0.08 mm⁻¹
c = 23.045 (2) Å	T = 173 K
V = 1950.5 (3) Å³	Block, colorless
Z = 8	0.45 × 0.30 × 0.30 mm

Data collection top

Bruker APEXII CCD diffractometer	1814 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.060
Graphite monochromator	θ_max = 27.0°, θ_min = 2.8°
ϕ and ω scans	h = −18→18
11034 measured reflections	k = −7→7
2182 independent reflections	l = −21→29

Refinement top

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0449P)² + 1.1368P] where P = (F_o² + 2F_c²)/3
2182 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.20 e Å⁻³
1 restraint	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₁H₁₁N₃	V = 1950.5 (3) Å³
M_r = 185.23	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 14.5434 (14) Å	µ = 0.08 mm⁻¹
b = 5.8198 (6) Å	T = 173 K
c = 23.045 (2) Å	0.45 × 0.30 × 0.30 mm

Data collection top

Bruker APEXII CCD diffractometer	1814 reflections with I > 2σ(I)
11034 measured reflections	R_int = 0.060
2182 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	1 restraint
wR(F²) = 0.124	H-atom parameters constrained
S = 1.10	Δρ_max = 0.20 e Å⁻³
2182 reflections	Δρ_min = −0.26 e Å⁻³
253 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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 > σ(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.

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

	x	y	z	U_iso*/U_eq
N1	0.4906 (2)	0.8350 (5)	0.22165 (14)	0.0310 (7)
N2	0.3345 (2)	0.2870 (6)	0.38908 (15)	0.0372 (8)
N3	0.4145 (3)	0.5075 (5)	0.24813 (15)	0.0324 (8)
H3N	0.3691	0.5445	0.2242	0.039*
C1	0.5596 (3)	0.9839 (7)	0.2290 (2)	0.0361 (10)
H1	0.5633	1.1100	0.2029	0.043*
C2	0.6248 (3)	0.9682 (8)	0.2711 (2)	0.0416 (12)
H2	0.6728	1.0781	0.2741	0.050*
C3	0.6183 (3)	0.7845 (8)	0.30973 (18)	0.0398 (10)
H3	0.6617	0.7693	0.3403	0.048*
C4	0.5493 (3)	0.6254 (7)	0.30356 (17)	0.0346 (9)
H4	0.5449	0.4978	0.3291	0.041*
C5	0.4854 (2)	0.6557 (6)	0.25870 (16)	0.0273 (8)
C6	0.3857 (3)	0.3394 (6)	0.29081 (18)	0.0332 (9)
H6A	0.4400	0.2470	0.3021	0.040*
H6B	0.3411	0.2340	0.2723	0.040*
C7	0.3424 (2)	0.4366 (6)	0.34538 (18)	0.0256 (8)
C8	0.3101 (3)	0.6580 (6)	0.3489 (2)	0.0435 (11)
H8	0.3184	0.7623	0.3176	0.052*
C9	0.2650 (4)	0.7265 (7)	0.3993 (2)	0.0528 (13)
H9	0.2412	0.8779	0.4026	0.063*
C10	0.2553 (3)	0.5742 (7)	0.4439 (2)	0.0421 (11)
H10	0.2245	0.6160	0.4787	0.050*
C11	0.2916 (3)	0.3591 (8)	0.43671 (19)	0.0424 (10)
H11	0.2857	0.2537	0.4680	0.051*
N4	0.2551 (2)	0.6738 (5)	0.17549 (13)	0.0287 (7)
N5	0.4108 (2)	1.2720 (5)	0.01448 (14)	0.0331 (7)
N6	0.3312 (3)	1.0014 (5)	0.14957 (16)	0.0347 (9)
H6N	0.3770	0.9641	0.1761	0.042*
C12	0.1866 (3)	0.5246 (7)	0.1674 (2)	0.0336 (10)
H12	0.1807	0.4016	0.1943	0.040*
C13	0.1236 (3)	0.5373 (7)	0.1227 (2)	0.0396 (11)
H13	0.0763	0.4260	0.1184	0.048*
C14	0.1323 (3)	0.7189 (8)	0.08444 (18)	0.0417 (10)
H14	0.0906	0.7338	0.0529	0.050*
C15	0.2011 (3)	0.8777 (7)	0.09179 (17)	0.0359 (9)
H15	0.2072	1.0033	0.0657	0.043*
C16	0.2625 (2)	0.8514 (6)	0.13870 (17)	0.0282 (8)
C17	0.3582 (3)	1.1827 (6)	0.11029 (17)	0.0323 (8)
H17A	0.4007	1.2869	0.1311	0.039*
H17B	0.3027	1.2728	0.1001	0.039*
C18	0.4040 (2)	1.1067 (6)	0.05466 (17)	0.0255 (8)
C19	0.4391 (3)	0.8888 (6)	0.0460 (2)	0.0381 (10)
H19	0.4316	0.7733	0.0747	0.046*
C20	0.4848 (3)	0.8417 (7)	−0.0045 (2)	0.0487 (12)
H20	0.5108	0.6939	−0.0106	0.058*
C21	0.4930 (4)	1.0085 (8)	−0.0462 (2)	0.0458 (12)
H21	0.5244	0.9797	−0.0816	0.055*
C22	0.4541 (3)	1.2192 (7)	−0.03478 (18)	0.0387 (9)
H22	0.4583	1.3345	−0.0639	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0295 (17)	0.0376 (17)	0.0260 (17)	−0.0019 (14)	0.0012 (13)	0.0025 (14)
N2	0.043 (2)	0.0342 (17)	0.0342 (18)	0.0037 (15)	−0.0029 (16)	0.0128 (15)
N3	0.030 (2)	0.0433 (18)	0.024 (2)	−0.0028 (14)	0.0009 (17)	0.0062 (14)
C1	0.032 (2)	0.037 (2)	0.040 (3)	−0.0005 (16)	0.005 (2)	−0.0010 (18)
C2	0.028 (2)	0.053 (3)	0.044 (3)	−0.0048 (19)	0.002 (2)	−0.008 (2)
C3	0.024 (2)	0.061 (3)	0.034 (2)	0.0052 (18)	−0.0063 (17)	−0.005 (2)
C4	0.0283 (19)	0.050 (2)	0.025 (2)	0.0041 (18)	0.0005 (16)	0.0060 (18)
C5	0.0246 (18)	0.0343 (18)	0.0230 (18)	0.0020 (15)	0.0050 (15)	−0.0028 (16)
C6	0.035 (2)	0.0266 (17)	0.038 (2)	−0.0008 (16)	−0.0008 (18)	0.0007 (18)
C7	0.0192 (17)	0.0283 (17)	0.0292 (19)	−0.0044 (14)	−0.0030 (16)	0.0050 (15)
C8	0.047 (3)	0.0277 (19)	0.056 (3)	0.0024 (18)	0.016 (2)	0.014 (2)
C9	0.056 (3)	0.033 (2)	0.069 (3)	0.000 (2)	0.026 (3)	−0.003 (2)
C10	0.039 (2)	0.052 (2)	0.036 (3)	−0.008 (2)	0.009 (2)	−0.008 (2)
C11	0.043 (2)	0.055 (2)	0.029 (2)	0.001 (2)	0.0033 (19)	0.011 (2)
N4	0.0276 (17)	0.0320 (15)	0.0265 (17)	0.0025 (13)	0.0021 (13)	0.0006 (13)
N5	0.0383 (18)	0.0299 (16)	0.0310 (17)	0.0081 (14)	−0.0028 (15)	0.0027 (15)
N6	0.032 (2)	0.0382 (18)	0.034 (2)	−0.0037 (14)	−0.0074 (19)	0.0087 (15)
C12	0.028 (2)	0.0363 (19)	0.037 (2)	0.0048 (16)	0.009 (2)	−0.0018 (17)
C13	0.025 (2)	0.051 (2)	0.044 (3)	0.0010 (18)	0.001 (2)	−0.012 (2)
C14	0.027 (2)	0.067 (3)	0.031 (2)	0.0088 (19)	−0.0016 (17)	−0.004 (2)
C15	0.0261 (19)	0.048 (2)	0.033 (2)	0.0044 (17)	−0.0009 (17)	0.0066 (19)
C16	0.0249 (18)	0.0361 (18)	0.0237 (18)	0.0085 (15)	0.0019 (15)	0.0006 (16)
C17	0.035 (2)	0.0317 (19)	0.0303 (19)	0.0053 (16)	0.0031 (17)	0.0011 (17)
C18	0.0223 (16)	0.0235 (16)	0.0306 (19)	−0.0014 (15)	−0.0085 (16)	0.0005 (16)
C19	0.034 (2)	0.0250 (18)	0.055 (3)	0.0012 (16)	0.011 (2)	0.0082 (19)
C20	0.047 (3)	0.0262 (19)	0.073 (3)	0.0009 (18)	0.022 (2)	−0.008 (2)
C21	0.042 (3)	0.052 (2)	0.043 (3)	−0.0035 (19)	0.012 (2)	−0.014 (2)
C22	0.045 (2)	0.046 (2)	0.0252 (19)	−0.0010 (19)	−0.0057 (19)	0.0028 (18)

Geometric parameters (Å, º) top

N1—C1	1.336 (5)	N4—C12	1.335 (5)
N1—C5	1.350 (5)	N4—C16	1.341 (5)
N2—C11	1.331 (6)	N5—C22	1.334 (5)
N2—C7	1.337 (5)	N5—C18	1.339 (5)
N3—C5	1.365 (5)	N6—C16	1.351 (5)
N3—C6	1.449 (5)	N6—C17	1.445 (5)
N3—H3N	0.8867	N6—H6N	0.9301
C1—C2	1.360 (7)	C12—C13	1.382 (6)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.394 (7)	C13—C14	1.382 (6)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.373 (6)	C14—C15	1.373 (6)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.401 (5)	C15—C16	1.410 (5)
C4—H4	0.9500	C15—H15	0.9500
C6—C7	1.516 (6)	C17—C18	1.511 (6)
C6—H6A	0.9900	C17—H17A	0.9900
C6—H6B	0.9900	C17—H17B	0.9900
C7—C8	1.374 (5)	C18—C19	1.381 (5)
C8—C9	1.391 (7)	C19—C20	1.367 (6)
C8—H8	0.9500	C19—H19	0.9500
C9—C10	1.365 (7)	C20—C21	1.372 (7)
C9—H9	0.9500	C20—H20	0.9500
C10—C11	1.368 (6)	C21—C22	1.376 (6)
C10—H10	0.9500	C21—H21	0.9500
C11—H11	0.9500	C22—H22	0.9500

C1—N1—C5	117.6 (3)	C12—N4—C16	118.2 (3)
C11—N2—C7	117.2 (3)	C22—N5—C18	117.2 (3)
C5—N3—C6	121.6 (3)	C16—N6—C17	123.8 (4)
C5—N3—H3N	121.3	C16—N6—H6N	120.1
C6—N3—H3N	111.7	C17—N6—H6N	112.9
N1—C1—C2	124.8 (4)	N4—C12—C13	124.4 (4)
N1—C1—H1	117.6	N4—C12—H12	117.8
C2—C1—H1	117.6	C13—C12—H12	117.8
C1—C2—C3	117.4 (4)	C12—C13—C14	117.1 (4)
C1—C2—H2	121.3	C12—C13—H13	121.4
C3—C2—H2	121.3	C14—C13—H13	121.4
C4—C3—C2	120.0 (4)	C15—C14—C13	120.2 (4)
C4—C3—H3	120.0	C15—C14—H14	119.9
C2—C3—H3	120.0	C13—C14—H14	119.9
C3—C4—C5	118.5 (4)	C14—C15—C16	118.9 (4)
C3—C4—H4	120.8	C14—C15—H15	120.6
C5—C4—H4	120.8	C16—C15—H15	120.6
N1—C5—N3	114.7 (3)	N4—C16—N6	116.1 (3)
N1—C5—C4	121.7 (3)	N4—C16—C15	121.2 (3)
N3—C5—C4	123.5 (3)	N6—C16—C15	122.7 (4)
N3—C6—C7	115.5 (3)	N6—C17—C18	115.9 (3)
N3—C6—H6A	108.4	N6—C17—H17A	108.3
C7—C6—H6A	108.4	C18—C17—H17A	108.3
N3—C6—H6B	108.4	N6—C17—H17B	108.3
C7—C6—H6B	108.4	C18—C17—H17B	108.3
H6A—C6—H6B	107.5	H17A—C17—H17B	107.4
N2—C7—C8	122.5 (4)	N5—C18—C19	122.2 (4)
N2—C7—C6	114.7 (3)	N5—C18—C17	114.1 (3)
C8—C7—C6	122.8 (4)	C19—C18—C17	123.7 (3)
C7—C8—C9	118.6 (4)	C20—C19—C18	119.1 (4)
C7—C8—H8	120.7	C20—C19—H19	120.5
C9—C8—H8	120.7	C18—C19—H19	120.5
C10—C9—C8	119.4 (4)	C19—C20—C21	119.8 (4)
C10—C9—H9	120.3	C19—C20—H20	120.1
C8—C9—H9	120.3	C21—C20—H20	120.1
C9—C10—C11	117.6 (4)	C20—C21—C22	117.4 (4)
C9—C10—H10	121.2	C20—C21—H21	121.3
C11—C10—H10	121.2	C22—C21—H21	121.3
N2—C11—C10	124.7 (4)	N5—C22—C21	124.2 (4)
N2—C11—H11	117.7	N5—C22—H22	117.9
C10—C11—H11	117.7	C21—C22—H22	117.9

C5—N1—C1—C2	0.0 (6)	N4—C12—C13—C14	−0.8 (6)
N1—C1—C2—C3	−0.8 (7)	C12—C13—C14—C15	−0.2 (6)
C1—C2—C3—C4	1.5 (6)	C13—C14—C15—C16	0.3 (6)
C2—C3—C4—C5	−1.3 (6)	C12—N4—C16—N6	178.1 (4)
C1—N1—C5—N3	−178.8 (4)	C12—N4—C16—C15	−1.6 (5)
C1—N1—C5—C4	0.2 (5)	C17—N6—C16—N4	170.6 (3)
C6—N3—C5—N1	−165.2 (3)	C17—N6—C16—C15	−9.7 (6)
C6—N3—C5—C4	15.8 (6)	C14—C15—C16—N4	0.6 (6)
C3—C4—C5—N1	0.5 (6)	C14—C15—C16—N6	−179.0 (4)
C3—C4—C5—N3	179.3 (4)	C16—N6—C17—C18	−69.3 (5)
C5—N3—C6—C7	67.4 (5)	C22—N5—C18—C19	−0.7 (6)
C11—N2—C7—C8	1.5 (6)	C22—N5—C18—C17	177.2 (3)
C11—N2—C7—C6	−175.8 (3)	N6—C17—C18—N5	166.9 (3)
N3—C6—C7—N2	−166.2 (3)	N6—C17—C18—C19	−15.2 (5)
N3—C6—C7—C8	16.5 (5)	N5—C18—C19—C20	2.1 (6)
N2—C7—C8—C9	−2.0 (7)	C17—C18—C19—C20	−175.6 (4)
C6—C7—C8—C9	175.1 (4)	C18—C19—C20—C21	−1.7 (7)
C7—C8—C9—C10	1.0 (8)	C19—C20—C21—C22	0.1 (7)
C8—C9—C10—C11	0.4 (7)	C18—N5—C22—C21	−1.1 (6)
C7—N2—C11—C10	0.0 (7)	C20—C21—C22—N5	1.4 (7)
C9—C10—C11—N2	−1.0 (7)	C5—N3—C6—C7	67.4 (5)
C16—N4—C12—C13	1.7 (6)	C16—N6—C17—C18	−69.3 (5)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N4/C12–C16, N2/C7–C11 and N5/C18–C22 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N4	0.89	2.14	3.019 (5)	172
N6—H6N···N1	0.93	2.10	3.012 (5)	168
C1—H1···Cg1ⁱ	0.95	2.77	3.53	137
C3—H3···Cg2ⁱⁱ	0.95	2.85	3.69	147
C14—H14···Cg3ⁱⁱⁱ	0.95	2.65	3.51	149

Symmetry codes: (i) x+1/2, −y+2, z; (ii) x+1/2, −y+1, z; (iii) x−1/2, −y+2, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₃
M_r	185.23
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	173
a, b, c (Å)	14.5434 (14), 5.8198 (6), 23.045 (2)
V (Å³)	1950.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.30 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11034, 2182, 1814
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.124, 1.10
No. of reflections	2182
No. of parameters	253
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.26

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N4/C12–C16, N2/C7–C11 and N5/C18–C22 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N4	0.89	2.14	3.019 (5)	172
N6—H6N···N1	0.93	2.10	3.012 (5)	168
C1—H1···Cg1ⁱ	0.95	2.77	3.53	137
C3—H3···Cg2ⁱⁱ	0.95	2.85	3.69	147
C14—H14···Cg3ⁱⁱⁱ	0.95	2.65	3.51	149

Symmetry codes: (i) x+1/2, −y+2, z; (ii) x+1/2, −y+1, z; (iii) x−1/2, −y+2, z.

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2010–0022675).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Foxon, S. P., Walter, O. & Schindler, S. (2002). Eur. J. Inorg. Chem. pp. 111–121. CSD CrossRef Google Scholar
Lee, S., Park, S., Kang, Y., Moon, S.-H., Lee, S. S. & Park, K.-M. (2008). Bull. Korean Chem. Soc. 29, 1811–1814. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 6| June 2011| Page o1355

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