4-(1H-Pyrrolo­[2,3-b]pyridin-2-yl)pyridine

Huang, P.-H.; Wen, Y.-S.; Shen, J.-Y.

doi:10.1107/S1600536813008672

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o674

https://doi.org/10.1107/S1600536813008672

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4-(1H-Pyrrolo[2,3-b]pyridin-2-yl)pyridine

Ping-Hsin Huang,^a ^* Yuh-Sheng Wen ^b and Jiun-Yi Shen ^c

^aCardinal Tien College of Healthcare & Management, Taipei, Taiwan 231, Republic of China, ^bInstitute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan, Republic of China, and ^cDepartment of Chemistry, National Taiwan University, Taipei, Taiwan, Republic of China
^*Correspondence e-mail: pshuang@ctcn.edu.tw

(Received 12 March 2013; accepted 29 March 2013; online 10 April 2013)

The asymmetric unit of the title compound, C₁₂H₉N₃, contains two independent molecules in which the dihedral angle between the pyridine and azaindole rings are 8.23 (6) and 9.89 (2)°. In the crystal, both types of molecule are connected by pairs of N—H—N hydrogen bonds into inversion dimers.

Related literature

For the production of luminescent organic compounds, see: Liu et al. (2000 ); Parcerisa et al. (2008 ). For related structures, see: Huang et al. (2012 ).

Experimental

Crystal data

C₁₂H₉N₃
M_r = 195.22
Triclinic, $[P \overline 1]$
a = 6.5529 (5) Å
b = 10.0457 (8) Å
c = 14.5282 (11) Å
α = 83.372 (2)°
β = 86.697 (2)°
γ = 87.427 (2)°
V = 947.69 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.975, T_max = 0.996
10193 measured reflections
3329 independent reflections
2573 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.124
S = 1.14
3329 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.86	2.22	3.061 (3)	167
N4—H4A⋯N5ⁱⁱ	0.86	2.22	3.066 (3)	169
Symmetry codes: (i) -x, -y+2, -z+2; (ii) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813008672/nc2308sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008672/nc2308Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813008672/nc2308Isup3.cml

checkCIF report

Comment top

The title compound has been shown to be an precursor for the production of luminescent organic compound (Liu et al., 2000). In the crystal structure of the title compound two crystallographically independent molecules are found which shows no large structural differences. Both molecules are nearly coplanar, the dihedral angles between the pyridine and the azaindole rings is 8.23 (6)° and 9.89 (2)° (Huang et al., 2012). Each of these molecules is connected into centrosymmetrically dimers by intermolecular N—H—N hydrogen bonding.

Related literature top

For the production of luminescent organic compounds, see: Liu et al. (2000); Parcerisa et al. (2008). For related structures, see: Huang et al. (2012).

Experimental top

The compound was synthesized by the following procedure (Parcerisa et al., 2008). A solution of [3-(2-hydroxy-2-pyridin-4-yl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (1 mmol and acetonitrile (12 ml) was cooled to ice temperature. Afterwards triethylamine (1.2 mmol) and trifluoromethanesulfonic anhydride (1.1 mmol) was added over a period of 5 min. The mixture was stirred at room temperature for 2 h, trifluoroacetic acid was added (1.5 mmol) and afterwards the mixture was heated under reflux for 1 h. The mixture was cooled to room temperature and neutralized using 2 N NaOH. The aqueous layer was extracted with ethyl ether and the organic extract was washed with brine and aqueous Na₂SO₄, dried and concentrated. The residue was purified by column chromatography using hexane/ethyl acetate (2:8) as eluent, followed by recrystallization in CH₂Cl₂ and hexane to give a white solid in 64% yield. Crystals suitable for X-ray diffraction were grown from a CH₂Cl₂ solution layered with hexane at room temperature. ¹H NMR (CDCl₃, 300 MHz): 8.62 (dd, 2 H, J= 1.0, 3.1 Hz), 8.29 (dd, 1 H, J= 1.0, 3.4 Hz), 8.00 (dd, 1 H, J = 1.0, 5.3 Hz), 7.72 (dd, 2 H, J = 1.0, 3.1 Hz), 7.13 (dd, 1 H, J= 3.4, 5.3 Hz), 6.99 (s, 1 H), Anal. Calcd for C₁₂H₉N₃: C, 73.83; H, 4.65; N, 21.52. Found: C, 74.21; H, 4.40; N, 21.34.

Structure description top

For the production of luminescent organic compounds, see: Liu et al. (2000); Parcerisa et al. (2008). For related structures, see: Huang et al. (2012).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. Molecular structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radii.

4-(1H-Pyrrolo[2,3-b]pyridin-2-yl)pyridine top

Crystal data top

C₁₂H₉N₃	Z = 4
M_r = 195.22	F(000) = 408
Triclinic, P1	D_x = 1.368 Mg m⁻³ D_m = 1.368 Mg m⁻³ D_m measured by not measured
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5529 (5) Å	Cell parameters from 1585 reflections
b = 10.0457 (8) Å	θ = 2.6–23.3°
c = 14.5282 (11) Å	µ = 0.09 mm⁻¹
α = 83.372 (2)°	T = 295 K
β = 86.697 (2)°	Plate, colorless
γ = 87.427 (2)°	0.30 × 0.20 × 0.05 mm
V = 947.69 (13) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3329 independent reflections
Radiation source: fine-focus sealed tube	2573 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
T_min = 0.975, T_max = 0.996	k = −11→11
10193 measured reflections	l = −17→17

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0442P)² + 0.126P] where P = (F_o² + 2F_c²)/3
3329 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₂H₉N₃	γ = 87.427 (2)°
M_r = 195.22	V = 947.69 (13) Å³
Triclinic, P1	Z = 4
a = 6.5529 (5) Å	Mo Kα radiation
b = 10.0457 (8) Å	µ = 0.09 mm⁻¹
c = 14.5282 (11) Å	T = 295 K
α = 83.372 (2)°	0.30 × 0.20 × 0.05 mm
β = 86.697 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3329 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2573 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.996	R_int = 0.034
10193 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.14	Δρ_max = 0.14 e Å⁻³
3329 reflections	Δρ_min = −0.17 e Å⁻³
271 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	0.2449 (3)	0.99700 (17)	0.92427 (12)	0.0443 (5)
H1	0.1787	1.0568	0.9532	0.053*
N2	−0.0037 (3)	0.82637 (19)	0.94609 (13)	0.0523 (5)
N3	0.7664 (4)	1.3698 (2)	0.86462 (16)	0.0704 (6)
N4	0.7252 (3)	0.97632 (17)	0.57580 (12)	0.0452 (5)
H4A	0.6651	1.0437	0.5450	0.054*
N5	0.4869 (3)	0.80868 (19)	0.55706 (13)	0.0524 (5)
N6	1.2240 (4)	1.3404 (2)	0.62691 (16)	0.0710 (6)
C1	0.4379 (3)	1.0098 (2)	0.88094 (14)	0.0423 (5)
C2	0.4911 (3)	0.8951 (2)	0.84219 (15)	0.0493 (6)
H2	0.6131	0.8780	0.8089	0.059*
C3	0.3285 (3)	0.8067 (2)	0.86152 (15)	0.0435 (5)
C4	0.2881 (4)	0.6784 (2)	0.84216 (16)	0.0548 (6)
H4	0.3826	0.6290	0.8083	0.066*
C5	0.1035 (4)	0.6273 (2)	0.87473 (17)	0.0576 (7)
H5	0.0713	0.5418	0.8630	0.069*
C6	−0.0344 (4)	0.7025 (2)	0.92484 (17)	0.0589 (7)
H6	−0.1580	0.6644	0.9454	0.071*
C7	0.1773 (3)	0.8734 (2)	0.91330 (14)	0.0416 (5)
C8	0.5755 (5)	1.3615 (3)	0.90108 (19)	0.0712 (8)
H8	0.5140	1.4376	0.9232	0.085*
C9	0.4636 (4)	1.2481 (2)	0.90816 (18)	0.0603 (7)
H9	0.3301	1.2493	0.9337	0.072*
C10	0.5497 (3)	1.1326 (2)	0.87731 (14)	0.0445 (5)
C11	0.7495 (4)	1.1396 (2)	0.84044 (16)	0.0561 (6)
H11	0.8162	1.0644	0.8193	0.067*
C12	0.8479 (4)	1.2578 (3)	0.83527 (18)	0.0678 (7)
H12	0.9811	1.2597	0.8094	0.081*
C13	0.9063 (3)	0.9796 (2)	0.61960 (14)	0.0424 (5)
C14	0.9524 (3)	0.8542 (2)	0.66219 (15)	0.0485 (6)
H14	1.0656	0.8293	0.6969	0.058*
C15	0.7970 (3)	0.7688 (2)	0.64396 (14)	0.0436 (5)
C16	0.7536 (4)	0.6348 (2)	0.66723 (16)	0.0554 (6)
H16	0.8395	0.5771	0.7035	0.066*
C17	0.5792 (4)	0.5904 (2)	0.63473 (17)	0.0573 (6)
H17	0.5454	0.5012	0.6486	0.069*
C18	0.4535 (4)	0.6788 (2)	0.58133 (17)	0.0557 (6)
H18	0.3366	0.6450	0.5607	0.067*
C19	0.6574 (3)	0.8490 (2)	0.58945 (14)	0.0415 (5)
C20	1.0412 (5)	1.3402 (3)	0.59264 (18)	0.0692 (8)
H20	0.9818	1.4225	0.5701	0.083*
C21	0.9327 (4)	1.2275 (2)	0.58795 (16)	0.0566 (6)
H21	0.8044	1.2350	0.5631	0.068*
C22	1.0152 (3)	1.1027 (2)	0.62031 (14)	0.0444 (5)
C23	1.2075 (4)	1.1013 (2)	0.65608 (17)	0.0559 (6)
H23	1.2712	1.0205	0.6787	0.067*
C24	1.3034 (4)	1.2199 (3)	0.65792 (18)	0.0672 (7)
H24	1.4319	1.2159	0.6824	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0419 (10)	0.0413 (11)	0.0508 (11)	−0.0013 (8)	0.0011 (9)	−0.0113 (8)
N2	0.0454 (11)	0.0507 (12)	0.0623 (13)	−0.0102 (9)	0.0003 (9)	−0.0112 (9)
N3	0.0765 (16)	0.0626 (16)	0.0714 (15)	−0.0247 (13)	−0.0063 (12)	0.0053 (12)
N4	0.0435 (11)	0.0392 (11)	0.0524 (11)	−0.0022 (8)	−0.0088 (9)	−0.0003 (8)
N5	0.0511 (12)	0.0480 (12)	0.0583 (12)	−0.0112 (9)	−0.0108 (9)	0.0003 (9)
N6	0.0781 (17)	0.0669 (16)	0.0707 (15)	−0.0277 (13)	0.0007 (13)	−0.0125 (12)
C1	0.0354 (12)	0.0475 (14)	0.0435 (13)	−0.0009 (10)	−0.0020 (10)	−0.0034 (10)
C2	0.0432 (13)	0.0539 (15)	0.0498 (14)	0.0005 (11)	0.0038 (11)	−0.0054 (11)
C3	0.0457 (13)	0.0409 (13)	0.0441 (13)	0.0020 (10)	−0.0037 (10)	−0.0057 (10)
C4	0.0627 (16)	0.0474 (15)	0.0542 (15)	0.0029 (12)	0.0004 (12)	−0.0089 (11)
C5	0.0703 (17)	0.0414 (14)	0.0629 (16)	−0.0094 (12)	−0.0066 (13)	−0.0096 (11)
C6	0.0570 (15)	0.0540 (16)	0.0674 (17)	−0.0163 (12)	−0.0014 (13)	−0.0095 (13)
C7	0.0408 (12)	0.0412 (13)	0.0439 (13)	−0.0038 (10)	−0.0064 (10)	−0.0062 (10)
C8	0.080 (2)	0.0510 (17)	0.083 (2)	−0.0045 (14)	−0.0019 (16)	−0.0076 (14)
C9	0.0568 (15)	0.0499 (16)	0.0747 (18)	−0.0087 (12)	0.0038 (13)	−0.0109 (13)
C10	0.0477 (13)	0.0461 (14)	0.0394 (12)	−0.0052 (10)	−0.0064 (10)	0.0002 (10)
C11	0.0500 (14)	0.0573 (16)	0.0607 (16)	−0.0104 (12)	0.0045 (12)	−0.0049 (12)
C12	0.0593 (17)	0.076 (2)	0.0665 (18)	−0.0216 (15)	0.0066 (13)	0.0018 (15)
C13	0.0394 (12)	0.0457 (14)	0.0423 (12)	−0.0011 (10)	−0.0029 (10)	−0.0059 (10)
C14	0.0448 (13)	0.0499 (15)	0.0509 (14)	0.0019 (11)	−0.0111 (11)	−0.0034 (11)
C15	0.0465 (13)	0.0395 (13)	0.0439 (13)	0.0006 (10)	−0.0027 (10)	−0.0016 (10)
C16	0.0632 (16)	0.0461 (15)	0.0559 (15)	0.0016 (12)	−0.0070 (12)	−0.0009 (11)
C17	0.0707 (17)	0.0407 (14)	0.0604 (16)	−0.0123 (12)	−0.0045 (13)	−0.0010 (11)
C18	0.0556 (15)	0.0524 (16)	0.0595 (15)	−0.0157 (12)	−0.0078 (12)	−0.0004 (12)
C19	0.0431 (12)	0.0385 (13)	0.0429 (12)	−0.0062 (10)	−0.0006 (10)	−0.0040 (9)
C20	0.087 (2)	0.0538 (17)	0.0668 (18)	−0.0156 (15)	−0.0081 (16)	0.0007 (13)
C21	0.0595 (15)	0.0505 (15)	0.0601 (16)	−0.0079 (12)	−0.0115 (12)	−0.0013 (12)
C22	0.0440 (13)	0.0497 (14)	0.0403 (13)	−0.0053 (10)	0.0007 (10)	−0.0083 (10)
C23	0.0494 (14)	0.0582 (16)	0.0618 (16)	−0.0072 (12)	−0.0079 (12)	−0.0093 (12)
C24	0.0570 (16)	0.082 (2)	0.0658 (18)	−0.0206 (15)	−0.0063 (13)	−0.0156 (15)

Geometric parameters (Å, º) top

N1—C7	1.366 (2)	C8—H8	0.9300
N1—C1	1.384 (2)	C9—C10	1.378 (3)
N1—H1	0.8600	C9—H9	0.9300
N2—C7	1.338 (3)	C10—C11	1.387 (3)
N2—C6	1.343 (3)	C11—C12	1.368 (3)
N3—C12	1.329 (3)	C11—H11	0.9300
N3—C8	1.332 (3)	C12—H12	0.9300
N4—C19	1.362 (3)	C13—C14	1.367 (3)
N4—C13	1.382 (2)	C13—C22	1.457 (3)
N4—H4A	0.8600	C14—C15	1.416 (3)
N5—C19	1.334 (3)	C14—H14	0.9300
N5—C18	1.336 (3)	C15—C16	1.388 (3)
N6—C20	1.324 (3)	C15—C19	1.408 (3)
N6—C24	1.336 (3)	C16—C17	1.373 (3)
C1—C2	1.362 (3)	C16—H16	0.9300
C1—C10	1.457 (3)	C17—C18	1.384 (3)
C2—C3	1.413 (3)	C17—H17	0.9300
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.390 (3)	C20—C21	1.374 (3)
C3—C7	1.403 (3)	C20—H20	0.9300
C4—C5	1.373 (3)	C21—C22	1.384 (3)
C4—H4	0.9300	C21—H21	0.9300
C5—C6	1.381 (3)	C22—C23	1.390 (3)
C5—H5	0.9300	C23—C24	1.375 (3)
C6—H6	0.9300	C23—H23	0.9300
C8—C9	1.373 (3)	C24—H24	0.9300

C7—N1—C1	108.49 (17)	C12—C11—H11	120.1
C7—N1—H1	125.8	C10—C11—H11	120.1
C1—N1—H1	125.8	N3—C12—C11	124.5 (3)
C7—N2—C6	113.4 (2)	N3—C12—H12	117.7
C12—N3—C8	115.3 (2)	C11—C12—H12	117.7
C19—N4—C13	108.82 (17)	C14—C13—N4	108.76 (19)
C19—N4—H4A	125.6	C14—C13—C22	128.8 (2)
C13—N4—H4A	125.6	N4—C13—C22	122.39 (19)
C19—N5—C18	113.62 (19)	C13—C14—C15	107.79 (19)
C20—N6—C24	115.3 (2)	C13—C14—H14	126.1
C2—C1—N1	108.75 (19)	C15—C14—H14	126.1
C2—C1—C10	129.1 (2)	C16—C15—C19	117.3 (2)
N1—C1—C10	122.06 (19)	C16—C15—C14	136.3 (2)
C1—C2—C3	108.01 (19)	C19—C15—C14	106.40 (18)
C1—C2—H2	126.0	C17—C16—C15	117.6 (2)
C3—C2—H2	126.0	C17—C16—H16	121.2
C4—C3—C7	117.2 (2)	C15—C16—H16	121.2
C4—C3—C2	136.3 (2)	C16—C17—C18	119.9 (2)
C7—C3—C2	106.46 (19)	C16—C17—H17	120.0
C5—C4—C3	117.6 (2)	C18—C17—H17	120.0
C5—C4—H4	121.2	N5—C18—C17	125.2 (2)
C3—C4—H4	121.2	N5—C18—H18	117.4
C4—C5—C6	120.1 (2)	C17—C18—H18	117.4
C4—C5—H5	119.9	N5—C19—N4	125.41 (19)
C6—C5—H5	119.9	N5—C19—C15	126.4 (2)
N2—C6—C5	125.0 (2)	N4—C19—C15	108.23 (18)
N2—C6—H6	117.5	N6—C20—C21	124.8 (3)
C5—C6—H6	117.5	N6—C20—H20	117.6
N2—C7—N1	125.10 (19)	C21—C20—H20	117.6
N2—C7—C3	126.6 (2)	C20—C21—C22	119.7 (2)
N1—C7—C3	108.29 (18)	C20—C21—H21	120.2
N3—C8—C9	124.4 (3)	C22—C21—H21	120.2
N3—C8—H8	117.8	C21—C22—C23	116.1 (2)
C9—C8—H8	117.8	C21—C22—C13	122.5 (2)
C8—C9—C10	119.7 (2)	C23—C22—C13	121.3 (2)
C8—C9—H9	120.1	C24—C23—C22	119.7 (2)
C10—C9—H9	120.1	C24—C23—H23	120.1
C9—C10—C11	116.3 (2)	C22—C23—H23	120.1
C9—C10—C1	122.5 (2)	N6—C24—C23	124.3 (2)
C11—C10—C1	121.1 (2)	N6—C24—H24	117.8
C12—C11—C10	119.7 (2)	C23—C24—H24	117.8

C7—N1—C1—C2	0.5 (2)	C19—N4—C13—C14	−0.7 (2)
C7—N1—C1—C10	177.80 (18)	C19—N4—C13—C22	−178.17 (19)
N1—C1—C2—C3	−0.2 (2)	N4—C13—C14—C15	0.6 (2)
C10—C1—C2—C3	−177.3 (2)	C22—C13—C14—C15	177.8 (2)
C1—C2—C3—C4	179.9 (2)	C13—C14—C15—C16	−179.2 (3)
C1—C2—C3—C7	−0.1 (2)	C13—C14—C15—C19	−0.3 (2)
C7—C3—C4—C5	0.3 (3)	C19—C15—C16—C17	0.5 (3)
C2—C3—C4—C5	−179.7 (2)	C14—C15—C16—C17	179.3 (2)
C3—C4—C5—C6	0.0 (4)	C15—C16—C17—C18	−0.4 (4)
C7—N2—C6—C5	0.4 (3)	C19—N5—C18—C17	0.0 (3)
C4—C5—C6—N2	−0.3 (4)	C16—C17—C18—N5	0.1 (4)
C6—N2—C7—N1	179.2 (2)	C18—N5—C19—N4	−179.1 (2)
C6—N2—C7—C3	−0.1 (3)	C18—N5—C19—C15	0.2 (3)
C1—N1—C7—N2	−179.9 (2)	C13—N4—C19—N5	180.0 (2)
C1—N1—C7—C3	−0.5 (2)	C13—N4—C19—C15	0.6 (2)
C4—C3—C7—N2	−0.2 (3)	C16—C15—C19—N5	−0.5 (3)
C2—C3—C7—N2	179.8 (2)	C14—C15—C19—N5	−179.6 (2)
C4—C3—C7—N1	−179.60 (18)	C16—C15—C19—N4	178.96 (19)
C2—C3—C7—N1	0.4 (2)	C14—C15—C19—N4	−0.2 (2)
C12—N3—C8—C9	−0.9 (4)	C24—N6—C20—C21	0.4 (4)
N3—C8—C9—C10	0.8 (4)	N6—C20—C21—C22	−0.3 (4)
C8—C9—C10—C11	0.2 (4)	C20—C21—C22—C23	−0.1 (3)
C8—C9—C10—C1	−178.6 (2)	C20—C21—C22—C13	178.4 (2)
C2—C1—C10—C9	170.0 (2)	C14—C13—C22—C21	−168.3 (2)
N1—C1—C10—C9	−6.7 (3)	N4—C13—C22—C21	8.6 (3)
C2—C1—C10—C11	−8.7 (4)	C14—C13—C22—C23	10.1 (3)
N1—C1—C10—C11	174.5 (2)	N4—C13—C22—C23	−173.0 (2)
C9—C10—C11—C12	−0.9 (3)	C21—C22—C23—C24	0.2 (3)
C1—C10—C11—C12	177.9 (2)	C13—C22—C23—C24	−178.2 (2)
C8—N3—C12—C11	0.0 (4)	C20—N6—C24—C23	−0.2 (4)
C10—C11—C12—N3	0.9 (4)	C22—C23—C24—N6	−0.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.86	2.22	3.061 (3)	167
N4—H4A···N5ⁱⁱ	0.86	2.22	3.066 (3)	169

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

Experimental details

Crystal data
Chemical formula	C₁₂H₉N₃
M_r	195.22
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.5529 (5), 10.0457 (8), 14.5282 (11)
α, β, γ (°)	83.372 (2), 86.697 (2), 87.427 (2)
V (Å³)	947.69 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.05

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.975, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	10193, 3329, 2573
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.124, 1.14
No. of reflections	3329
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.17

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.86	2.22	3.061 (3)	167.0
N4—H4A···N5ⁱⁱ	0.86	2.22	3.066 (3)	168.6

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

Acknowledgements

This work is partially supported by the instrumentation center, National Taiwan University, and Cardinal Tien College of Healthcare & Management.

References

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Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
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