4-Methyl-6-phenyl­pyrimidin-2-amine

Li, Z.-J.; Huang, J.-E.; Meng, A.-L.

doi:10.1107/S1600536808008003

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o759

doi:10.1107/S1600536808008003

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4-Methyl-6-phenylpyrimidin-2-amine

Zhen-Jiang Li,^a ^* Jun-E Huang ^a and A-Lan Meng ^a

^aQingdao University of Science and Technology, Qingdao 266061, People's Republic of China
^*Correspondence e-mail: zjli126@126.com

(Received 24 December 2007; accepted 25 March 2008; online 29 March 2008)

The title compound, C₁₁H₁₁N₃, was synthesized as part of our research into functionalized pyrimidines. It crystallizes with two independent molecules in the asymmetric unit that differ only in the twist between the two aromatic rings; the torsion angles between the rings are 29.9 (2) and 45.1 (2)°. The crystal packing is dominated by intermolecular N—H⋯N hydrogen bonds between independent and equivalent molecules, forming an infinite three-dimensional network.

Related literature

For biological activity, see: Zhu & Yang (2005 ); Sherrington & Taskinen (2001 ); Ligthart et al. (2005 ). For a similar structure, see: Fun et al. (2006 ).

Experimental

Crystal data

C₁₁H₁₁N₃
M_r = 185.23
Monoclinic, P 2₁ /c
a = 14.0558 (11) Å
b = 9.3808 (7) Å
c = 18.5227 (12) Å
β = 125.950 (4)°
V = 1977.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 273 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.977, T_max = 0.985
17472 measured reflections
3619 independent reflections
2760 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.113
S = 1.04
3619 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3ⁱ	0.86	2.38	3.1918 (18)	157
N1—H1B⋯N6ⁱ	0.86	2.35	3.2095 (18)	175
N4—H4C⋯N2ⁱ	0.86	2.29	3.1474 (19)	176
N4—H4B⋯N5ⁱⁱ	0.86	2.24	3.0834 (18)	166
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks h-1, I. DOI: 10.1107/S1600536808008003/fl2182sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008003/fl2182Isup2.hkl

checkCIF report

Comment top

Pyrimidines are broadly used in the preparation of pesticides and medications (Zhu & Yang, 2005). Functionalized pyrimidines are important for the synthesis of purine- and pteridine-related compounds and also for multiple hydrogen-bonding interactions that play a role in molecular recognition and supramolecular chemistry (Sherrington & Taskinen, 2001; Ligthart et al., 2005). In the title compound, (I), (fig. 1) there are two molecules per asymmetric unit that differ only in the twist between the two aromatic rings with dihedral angles between the phenyl and pyrimidine rings of 29.41 (2)° 46.32 (3)°. Bond lengths and angles for (I) are generally normal (Fun et al., 2006).

In the packing there are intermolecular N—H···N hydrogen bonds that link each independent molecule to related self molecules as well as to the second molecule in the asymmetric unit to create an infinite network of hydrogen bonded molecules (Table 1, Fig. 2).

Related literature top

For biological activity, see: Zhu & Yang (2005); Sherrington & Taskinen (2001); Ligthart et al. (2005). For a similar structure, see: Fun et al. (2006).

Experimental top

The single crystals of the title compound were obtained by reaction of 1-phenylbutane-1,3-dione(0.2 mmol) with guanidine nitrate(0.2 mmol) by refluxing in DMF(50 ml). The product (yied 89%) was stirred in the DMF and single crystals of the title compound suitable for X-ray measurements were obtained by recrystallization from DMF at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. The molecular structure and atom-labeling scheme for (I), with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The packing of (I), showing one layer of molecules connected by N—H···N hydrogen bonds (dashed lines).

(I) top

Crystal data top

C₁₁H₁₁N₃	F(000) = 784
M_r = 185.23	D_x = 1.245 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 512 reflections
a = 14.0558 (11) Å	θ = 2–22°
b = 9.3808 (7) Å	µ = 0.08 mm⁻¹
c = 18.5227 (12) Å	T = 273 K
β = 125.950 (4)°	Block, colorless
V = 1977.1 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 8

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3619 independent reflections
Radiation source: fine-focus sealed tube	2760 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
thin–slice ω scans	θ_max = 25.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→16
T_min = 0.977, T_max = 0.985	k = −11→11
17472 measured reflections	l = −22→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0535P)² + 0.393P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3619 reflections	Δρ_max = 0.21 e Å⁻³
256 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (13)

Crystal data top

C₁₁H₁₁N₃	V = 1977.1 (2) Å³
M_r = 185.23	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.0558 (11) Å	µ = 0.08 mm⁻¹
b = 9.3808 (7) Å	T = 273 K
c = 18.5227 (12) Å	0.30 × 0.20 × 0.20 mm
β = 125.950 (4)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	3619 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2760 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.985	R_int = 0.033
17472 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.04	Δρ_max = 0.21 e Å⁻³
3619 reflections	Δρ_min = −0.16 e Å⁻³
256 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	1.09631 (12)	−0.10203 (14)	0.46842 (9)	0.0492 (4)
H1A	1.0775	−0.1072	0.5049	0.059*
H1B	1.1590	−0.1434	0.4810	0.059*
N2	1.06247 (11)	−0.02652 (14)	0.33737 (9)	0.0445 (3)
N3	0.93111 (10)	0.03294 (12)	0.37592 (8)	0.0371 (3)
C1	0.69500 (14)	0.10273 (16)	0.31097 (10)	0.0428 (4)
H1C	0.7276	0.0232	0.3478	0.051*
C2	0.59049 (15)	0.1585 (2)	0.28979 (12)	0.0537 (4)
H2B	0.5531	0.1161	0.3123	0.064*
C3	0.54156 (17)	0.2762 (2)	0.23573 (13)	0.0661 (5)
H3B	0.4718	0.3143	0.2223	0.079*
C4	0.59617 (19)	0.3378 (2)	0.20139 (14)	0.0711 (6)
H4A	0.5627	0.4168	0.1642	0.085*
C5	0.70011 (16)	0.28266 (19)	0.22208 (12)	0.0557 (5)
H5A	0.7363	0.3249	0.1986	0.067*
C6	0.75185 (13)	0.16463 (15)	0.27758 (10)	0.0395 (4)
C7	0.86232 (13)	0.10283 (14)	0.29811 (10)	0.0370 (3)
C8	0.89113 (14)	0.11063 (17)	0.23828 (11)	0.0462 (4)
H8A	0.8435	0.1598	0.1847	0.055*
C9	1.02765 (13)	−0.02917 (15)	0.39158 (10)	0.0371 (3)
C10	0.99219 (14)	0.04372 (18)	0.26026 (11)	0.0457 (4)
C11	1.02670 (19)	0.0447 (3)	0.19755 (13)	0.0730 (6)
H11A	1.1108	0.0476	0.2311	0.109*
H11B	0.9937	0.1271	0.1597	0.109*
H11C	0.9977	−0.0400	0.1616	0.109*
N4	0.66133 (12)	0.04458 (13)	0.54000 (9)	0.0466 (4)
H4B	0.6190	−0.0240	0.5377	0.056*
H4C	0.7366	0.0363	0.5722	0.056*
N5	0.49149 (11)	0.17062 (13)	0.44429 (9)	0.0440 (3)
N6	0.68078 (11)	0.26712 (12)	0.49771 (8)	0.0379 (3)
C12	0.78707 (15)	0.46852 (17)	0.44133 (12)	0.0494 (4)
H12A	0.7997	0.3741	0.4339	0.059*
C13	0.85244 (17)	0.5759 (2)	0.43871 (13)	0.0597 (5)
H13A	0.9080	0.5533	0.4285	0.072*
C14	0.83596 (17)	0.7156 (2)	0.45107 (13)	0.0644 (5)
H14A	0.8809	0.7871	0.4499	0.077*
C15	0.75362 (19)	0.74936 (19)	0.46501 (15)	0.0683 (6)
H15A	0.7429	0.8438	0.4740	0.082*
C16	0.68603 (17)	0.64335 (17)	0.46588 (13)	0.0566 (5)
H16A	0.6286	0.6674	0.4738	0.068*
C17	0.70284 (13)	0.50159 (15)	0.45505 (10)	0.0404 (4)
C18	0.62748 (13)	0.38817 (15)	0.45327 (10)	0.0387 (4)
C19	0.50733 (14)	0.40570 (17)	0.40489 (11)	0.0471 (4)
H19A	0.4721	0.4919	0.3770	0.057*
C20	0.60975 (13)	0.16496 (15)	0.49325 (10)	0.0376 (3)
C21	0.44081 (14)	0.29142 (17)	0.39901 (11)	0.0475 (4)
C22	0.30886 (16)	0.2934 (2)	0.33834 (15)	0.0744 (6)
H22A	0.2787	0.2262	0.3593	0.112*
H22B	0.2823	0.2681	0.2790	0.112*
H22C	0.2812	0.3872	0.3379	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0443 (8)	0.0635 (8)	0.0430 (8)	0.0156 (6)	0.0274 (7)	0.0176 (7)
N2	0.0398 (7)	0.0573 (8)	0.0382 (8)	0.0040 (6)	0.0239 (7)	0.0047 (6)
N3	0.0349 (7)	0.0422 (6)	0.0335 (7)	0.0002 (5)	0.0196 (6)	0.0031 (5)
C1	0.0399 (9)	0.0490 (8)	0.0359 (9)	−0.0024 (7)	0.0202 (8)	−0.0030 (7)
C2	0.0455 (10)	0.0717 (11)	0.0479 (10)	−0.0032 (9)	0.0296 (9)	−0.0102 (9)
C3	0.0497 (11)	0.0876 (14)	0.0552 (12)	0.0223 (10)	0.0275 (10)	0.0005 (10)
C4	0.0712 (13)	0.0751 (13)	0.0652 (13)	0.0330 (11)	0.0391 (12)	0.0220 (10)
C5	0.0577 (11)	0.0579 (10)	0.0533 (11)	0.0135 (8)	0.0335 (10)	0.0141 (8)
C6	0.0377 (8)	0.0430 (8)	0.0328 (8)	0.0007 (6)	0.0179 (7)	−0.0014 (6)
C7	0.0351 (8)	0.0379 (7)	0.0334 (8)	−0.0026 (6)	0.0175 (7)	0.0012 (6)
C8	0.0432 (9)	0.0582 (9)	0.0353 (9)	0.0052 (7)	0.0220 (8)	0.0109 (7)
C9	0.0345 (8)	0.0403 (7)	0.0341 (8)	−0.0017 (6)	0.0187 (7)	0.0013 (6)
C10	0.0414 (9)	0.0617 (10)	0.0351 (9)	0.0007 (7)	0.0230 (8)	0.0039 (7)
C11	0.0642 (13)	0.1156 (17)	0.0521 (12)	0.0198 (12)	0.0414 (11)	0.0190 (11)
N4	0.0396 (7)	0.0426 (7)	0.0574 (9)	0.0040 (6)	0.0284 (7)	0.0128 (6)
N5	0.0377 (7)	0.0477 (7)	0.0461 (8)	0.0007 (6)	0.0243 (7)	0.0095 (6)
N6	0.0385 (7)	0.0396 (6)	0.0385 (7)	−0.0002 (5)	0.0242 (6)	0.0026 (5)
C12	0.0520 (10)	0.0467 (9)	0.0570 (11)	0.0015 (7)	0.0363 (9)	0.0049 (7)
C13	0.0559 (11)	0.0681 (11)	0.0666 (13)	−0.0038 (9)	0.0425 (10)	0.0081 (9)
C14	0.0619 (12)	0.0561 (11)	0.0710 (13)	−0.0176 (9)	0.0367 (11)	0.0032 (9)
C15	0.0769 (14)	0.0424 (9)	0.0895 (16)	−0.0120 (9)	0.0510 (13)	−0.0080 (9)
C16	0.0621 (11)	0.0473 (9)	0.0710 (12)	−0.0024 (8)	0.0449 (10)	−0.0038 (8)
C17	0.0416 (8)	0.0405 (8)	0.0381 (9)	−0.0007 (6)	0.0229 (7)	0.0038 (6)
C18	0.0429 (9)	0.0397 (8)	0.0378 (9)	0.0014 (6)	0.0260 (8)	0.0023 (6)
C19	0.0448 (10)	0.0448 (8)	0.0519 (10)	0.0071 (7)	0.0286 (9)	0.0139 (7)
C20	0.0391 (8)	0.0406 (7)	0.0366 (8)	0.0011 (6)	0.0243 (7)	0.0016 (6)
C21	0.0399 (9)	0.0543 (9)	0.0481 (10)	0.0049 (7)	0.0258 (8)	0.0125 (8)
C22	0.0415 (10)	0.0858 (14)	0.0792 (15)	0.0059 (10)	0.0261 (11)	0.0336 (12)

Geometric parameters (Å, º) top

N1—C9	1.3459 (19)	N4—C20	1.3467 (19)
N1—H1A	0.8600	N4—H4B	0.8600
N1—H1B	0.8600	N4—H4C	0.8600
N2—C10	1.339 (2)	N5—C21	1.339 (2)
N2—C9	1.3509 (19)	N5—C20	1.3484 (19)
N3—C9	1.3426 (19)	N6—C18	1.3431 (18)
N3—C7	1.3437 (18)	N6—C20	1.3510 (18)
C1—C2	1.382 (2)	C12—C13	1.383 (2)
C1—C6	1.392 (2)	C12—C17	1.384 (2)
C1—H1C	0.9300	C12—H12A	0.9300
C2—C3	1.374 (3)	C13—C14	1.373 (3)
C2—H2B	0.9300	C13—H13A	0.9300
C3—C4	1.379 (3)	C14—C15	1.363 (3)
C3—H3B	0.9300	C14—H14A	0.9300
C4—C5	1.375 (3)	C15—C16	1.382 (2)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.391 (2)	C16—C17	1.386 (2)
C5—H5A	0.9300	C16—H16A	0.9300
C6—C7	1.483 (2)	C17—C18	1.488 (2)
C7—C8	1.387 (2)	C18—C19	1.380 (2)
C8—C10	1.378 (2)	C19—C21	1.384 (2)
C8—H8A	0.9300	C19—H19A	0.9300
C10—C11	1.499 (2)	C21—C22	1.502 (2)
C11—H11A	0.9600	C22—H22A	0.9600
C11—H11B	0.9600	C22—H22B	0.9600
C11—H11C	0.9600	C22—H22C	0.9600

C9—N1—H1A	120.0	C20—N4—H4B	120.0
C9—N1—H1B	120.0	C20—N4—H4C	120.0
H1A—N1—H1B	120.0	H4B—N4—H4C	120.0
C10—N2—C9	116.07 (13)	C21—N5—C20	116.55 (13)
C9—N3—C7	116.30 (12)	C18—N6—C20	115.84 (12)
C2—C1—C6	120.52 (15)	C13—C12—C17	120.02 (16)
C2—C1—H1C	119.7	C13—C12—H12A	120.0
C6—C1—H1C	119.7	C17—C12—H12A	120.0
C3—C2—C1	120.35 (17)	C14—C13—C12	120.58 (17)
C3—C2—H2B	119.8	C14—C13—H13A	119.7
C1—C2—H2B	119.8	C12—C13—H13A	119.7
C2—C3—C4	119.81 (17)	C15—C14—C13	119.89 (16)
C2—C3—H3B	120.1	C15—C14—H14A	120.1
C4—C3—H3B	120.1	C13—C14—H14A	120.1
C5—C4—C3	120.12 (18)	C14—C15—C16	120.07 (17)
C5—C4—H4A	119.9	C14—C15—H15A	120.0
C3—C4—H4A	119.9	C16—C15—H15A	120.0
C4—C5—C6	120.95 (18)	C15—C16—C17	120.81 (17)
C4—C5—H5A	119.5	C15—C16—H16A	119.6
C6—C5—H5A	119.5	C17—C16—H16A	119.6
C5—C6—C1	118.24 (15)	C12—C17—C16	118.59 (15)
C5—C6—C7	121.01 (14)	C12—C17—C18	120.67 (14)
C1—C6—C7	120.72 (13)	C16—C17—C18	120.65 (14)
N3—C7—C8	121.26 (14)	N6—C18—C19	121.89 (13)
N3—C7—C6	116.84 (13)	N6—C18—C17	117.21 (13)
C8—C7—C6	121.83 (14)	C19—C18—C17	120.86 (13)
C10—C8—C7	118.27 (14)	C18—C19—C21	118.12 (14)
C10—C8—H8A	120.9	C18—C19—H19A	120.9
C7—C8—H8A	120.9	C21—C19—H19A	120.9
N3—C9—N1	117.08 (13)	N4—C20—N5	116.82 (13)
N3—C9—N2	126.34 (13)	N4—C20—N6	117.13 (13)
N1—C9—N2	116.58 (13)	N5—C20—N6	126.02 (13)
N2—C10—C8	121.75 (14)	N5—C21—C19	121.31 (14)
N2—C10—C11	117.25 (15)	N5—C21—C22	116.64 (15)
C8—C10—C11	120.99 (15)	C19—C21—C22	121.98 (15)
C10—C11—H11A	109.5	C21—C22—H22A	109.5
C10—C11—H11B	109.5	C21—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
C10—C11—H11C	109.5	C21—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5

C6—C1—C2—C3	−0.3 (2)	C17—C12—C13—C14	1.1 (3)
C1—C2—C3—C4	0.9 (3)	C12—C13—C14—C15	−0.8 (3)
C2—C3—C4—C5	−0.8 (3)	C13—C14—C15—C16	−0.6 (3)
C3—C4—C5—C6	0.0 (3)	C14—C15—C16—C17	1.7 (3)
C4—C5—C6—C1	0.7 (3)	C13—C12—C17—C16	0.0 (3)
C4—C5—C6—C7	178.44 (17)	C13—C12—C17—C18	176.76 (16)
C2—C1—C6—C5	−0.5 (2)	C15—C16—C17—C12	−1.4 (3)
C2—C1—C6—C7	−178.31 (14)	C15—C16—C17—C18	−178.14 (17)
C9—N3—C7—C8	−0.6 (2)	C20—N6—C18—C19	−1.1 (2)
C9—N3—C7—C6	176.50 (12)	C20—N6—C18—C17	−178.59 (13)
C5—C6—C7—N3	153.34 (15)	C12—C17—C18—N6	45.1 (2)
C1—C6—C7—N3	−28.9 (2)	C16—C17—C18—N6	−138.24 (16)
C5—C6—C7—C8	−29.6 (2)	C12—C17—C18—C19	−132.43 (17)
C1—C6—C7—C8	148.13 (15)	C16—C17—C18—C19	44.2 (2)
N3—C7—C8—C10	0.5 (2)	N6—C18—C19—C21	−3.4 (2)
C6—C7—C8—C10	−176.46 (14)	C17—C18—C19—C21	174.05 (15)
C7—N3—C9—N1	−178.71 (13)	C21—N5—C20—N4	179.01 (14)
C7—N3—C9—N2	0.8 (2)	C21—N5—C20—N6	−2.9 (2)
C10—N2—C9—N3	−0.9 (2)	C18—N6—C20—N4	−177.49 (13)
C10—N2—C9—N1	178.64 (14)	C18—N6—C20—N5	4.5 (2)
C9—N2—C10—C8	0.7 (2)	C20—N5—C21—C19	−2.0 (2)
C9—N2—C10—C11	−178.21 (16)	C20—N5—C21—C22	174.92 (16)
C7—C8—C10—N2	−0.6 (2)	C18—C19—C21—N5	5.0 (3)
C7—C8—C10—C11	178.35 (17)	C18—C19—C21—C22	−171.76 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3ⁱ	0.86	2.38	3.1918 (18)	157
N1—H1B···N6ⁱ	0.86	2.35	3.2095 (18)	175
N4—H4C···N2ⁱ	0.86	2.29	3.1474 (19)	176
N4—H4B···N5ⁱⁱ	0.86	2.24	3.0834 (18)	166

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₃
M_r	185.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	14.0558 (11), 9.3808 (7), 18.5227 (12)
β (°)	125.950 (4)
V (Å³)	1977.1 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.977, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	17472, 3619, 2760
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.113, 1.04
No. of reflections	3619
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.16

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3ⁱ	0.86	2.38	3.1918 (18)	156.6
N1—H1B···N6ⁱ	0.86	2.35	3.2095 (18)	174.6
N4—H4C···N2ⁱ	0.86	2.29	3.1474 (19)	176.4
N4—H4B···N5ⁱⁱ	0.86	2.24	3.0834 (18)	166.2

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

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province (grant No. Y2005F08).

References

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