N-[(E)-Quinoxalin-2-ylmethyl-idene]-1H-indazol-5-amine.

In the title mol-ecule, C(16)H(11)N(5), the mean planes of the quinoxaline and indazole fragments form a dihedral angle of 10.62 (5)°. In the crystal, weak inter-molecular N-H⋯N hydrogen bonds link the mol-ecules into zigzag chains extending in the [001] direction. The crystal packing also exhibits π-π inter-actions [centroid-centroid distances of 3.7080 (2) and 3.8220 (5) Å], which form stacks of the mol-ecules parallel to the a axis.

Related literature

For related structures, see: Varghese et al. (2009 ▶); Varsha et al. (2009 ▶).

Experimental

Crystal data

C16H11N5

M = 273.30

Monoclinic,

a = 7.7015 (6) Å

b = 8.0330 (6) Å

c = 20.6034 (16) Å

β = 96.882 (2)°

V = 1265.47 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.45 × 0.27 × 0.08 mm

Data collection

Bruker Kappa APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.960, T max = 0.993

16012 measured reflections

3597 independent reflections

2502 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.143

S = 1.03

3597 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global, schiflm. DOI: 10.1107/S1600536809027822/cv2578sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027822/cv2578Isup2.hkl

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

C16H11N5	F(000) = 568
Mr = 273.30	Dx = 1.434 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2502 reflections
a = 7.7015 (6) Å	θ = 2.6–29.8°
b = 8.0330 (6) Å	µ = 0.09 mm−1
c = 20.6034 (16) Å	T = 298 K
β = 96.882 (2)°	Plate, green
V = 1265.47 (17) Å3	0.45 × 0.27 × 0.08 mm
Z = 4

Bruker Kappa APEX CCD diffractometer	3597 independent reflections
Radiation source: fine-focus sealed tube	2502 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω and φ scans	θmax = 29.8°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.960, Tmax = 0.993	k = −11→10
16012 measured reflections	l = −28→26

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0715P)2 + 0.2171P] where P = (Fo2 + 2Fc2)/3
3597 reflections	(Δ/σ)max = 0.003
190 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.25032 (15)	0.66502 (15)	0.33833 (5)	0.0436 (3)
N2	0.14194 (13)	0.77204 (14)	0.45776 (5)	0.0392 (3)
N3	0.30313 (15)	0.37642 (14)	0.50779 (5)	0.0413 (3)
N4	0.38605 (15)	−0.08636 (16)	0.70573 (5)	0.0454 (3)
H4	0.3774	−0.0851	0.7470	0.054*
N5	0.42455 (17)	−0.22452 (16)	0.67229 (6)	0.0515 (3)
C1	0.18211 (15)	0.82051 (17)	0.34459 (6)	0.0368 (3)
C2	0.16182 (18)	0.9289 (2)	0.29041 (6)	0.0469 (3)
H2	0.1980	0.8960	0.2509	0.056*
C3	0.08916 (19)	1.0817 (2)	0.29612 (7)	0.0507 (4)
H3	0.0724	1.1511	0.2598	0.061*
C4	0.03910 (19)	1.1364 (2)	0.35576 (7)	0.0490 (4)
H4A	−0.0073	1.2426	0.3589	0.059*
C5	0.05790 (18)	1.03530 (18)	0.40912 (7)	0.0440 (3)
H5	0.0247	1.0724	0.4486	0.053*
C6	0.12780 (16)	0.87452 (17)	0.40443 (6)	0.0361 (3)
C7	0.26273 (18)	0.57069 (18)	0.39027 (6)	0.0436 (3)
H7	0.3088	0.4642	0.3877	0.052*
C8	0.20879 (16)	0.62367 (16)	0.45062 (6)	0.0374 (3)
C9	0.22517 (17)	0.51440 (18)	0.50816 (6)	0.0411 (3)
H9	0.1773	0.5475	0.5455	0.049*
C10	0.32246 (16)	0.27137 (17)	0.56339 (6)	0.0369 (3)
C11	0.36804 (16)	0.10932 (16)	0.55175 (6)	0.0375 (3)
H11	0.3848	0.0756	0.5098	0.045*
C12	0.38887 (16)	−0.00418 (17)	0.60359 (6)	0.0360 (3)
C13	0.36273 (15)	0.04951 (17)	0.66654 (6)	0.0365 (3)
C14	0.42856 (19)	−0.17552 (18)	0.61149 (6)	0.0460 (3)
H14	0.4543	−0.2451	0.5778	0.055*
C15	0.32249 (17)	0.21454 (18)	0.67939 (6)	0.0421 (3)
H15	0.3096	0.2496	0.7216	0.051*
C16	0.30258 (18)	0.32333 (18)	0.62789 (6)	0.0427 (3)
H16	0.2754	0.4339	0.6354	0.051*

	U11	U22	U33	U12	U13	U23
N1	0.0514 (6)	0.0477 (7)	0.0324 (5)	0.0016 (5)	0.0079 (4)	−0.0037 (5)
N2	0.0438 (6)	0.0433 (6)	0.0313 (5)	0.0018 (5)	0.0081 (4)	0.0014 (4)
N3	0.0508 (6)	0.0404 (6)	0.0333 (5)	−0.0004 (5)	0.0073 (4)	0.0023 (4)
N4	0.0577 (7)	0.0510 (7)	0.0279 (5)	−0.0001 (5)	0.0070 (5)	0.0050 (5)
N5	0.0698 (8)	0.0469 (7)	0.0377 (6)	0.0017 (6)	0.0070 (5)	0.0050 (5)
C1	0.0357 (6)	0.0445 (7)	0.0304 (6)	−0.0040 (5)	0.0046 (4)	−0.0005 (5)
C2	0.0492 (7)	0.0593 (9)	0.0333 (6)	−0.0023 (7)	0.0096 (5)	0.0060 (6)
C3	0.0494 (8)	0.0581 (9)	0.0453 (8)	−0.0007 (7)	0.0087 (6)	0.0184 (7)
C4	0.0473 (7)	0.0466 (8)	0.0536 (8)	0.0046 (6)	0.0085 (6)	0.0093 (7)
C5	0.0465 (7)	0.0465 (8)	0.0398 (7)	0.0042 (6)	0.0087 (5)	0.0011 (6)
C6	0.0355 (6)	0.0423 (7)	0.0307 (6)	−0.0030 (5)	0.0046 (4)	0.0000 (5)
C7	0.0530 (8)	0.0435 (8)	0.0347 (6)	0.0041 (6)	0.0065 (5)	−0.0026 (5)
C8	0.0401 (6)	0.0402 (7)	0.0322 (6)	−0.0015 (5)	0.0061 (5)	0.0006 (5)
C9	0.0452 (7)	0.0452 (8)	0.0338 (6)	0.0000 (6)	0.0087 (5)	0.0022 (5)
C10	0.0417 (6)	0.0405 (7)	0.0291 (6)	−0.0015 (5)	0.0071 (5)	0.0001 (5)
C11	0.0440 (6)	0.0435 (7)	0.0264 (5)	0.0002 (5)	0.0098 (5)	−0.0015 (5)
C12	0.0395 (6)	0.0406 (7)	0.0286 (6)	−0.0015 (5)	0.0067 (4)	−0.0007 (5)
C13	0.0367 (6)	0.0468 (8)	0.0264 (5)	−0.0026 (5)	0.0054 (4)	0.0012 (5)
C14	0.0604 (8)	0.0425 (8)	0.0356 (7)	0.0029 (6)	0.0075 (6)	0.0008 (6)
C15	0.0489 (7)	0.0516 (8)	0.0265 (6)	0.0014 (6)	0.0074 (5)	−0.0063 (5)
C16	0.0531 (7)	0.0420 (7)	0.0334 (6)	0.0038 (6)	0.0062 (5)	−0.0063 (5)

N1—C7	1.3053 (17)	C5—C6	1.4070 (19)
N1—C1	1.3670 (17)	C5—H5	0.9300
N2—C8	1.3136 (17)	C7—C8	1.4225 (17)
N2—C6	1.3668 (16)	C7—H7	0.9300
N3—C9	1.2610 (18)	C8—C9	1.4684 (17)
N3—C10	1.4162 (16)	C9—H9	0.9300
N4—C13	1.3568 (17)	C10—C11	1.3768 (18)
N4—N5	1.3576 (17)	C10—C16	1.4185 (17)
N4—H4	0.8600	C11—C12	1.3989 (17)
N5—C14	1.3169 (17)	C11—H11	0.9300
C1—C2	1.4094 (18)	C12—C13	1.4039 (16)
C1—C6	1.4167 (17)	C12—C14	1.4150 (19)
C2—C3	1.360 (2)	C13—C15	1.3941 (19)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.402 (2)	C15—C16	1.3691 (18)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.3605 (19)	C16—H16	0.9300
C4—H4A	0.9300
Cg1···Cg3i	3.7080 (2)	Cg2···Cg3ii	3.8220 (5)
C7—N1—C1	116.38 (11)	N2—C8—C7	121.92 (12)
C8—N2—C6	116.81 (10)	N2—C8—C9	116.67 (11)
C9—N3—C10	121.52 (11)	C7—C8—C9	121.40 (12)
C13—N4—N5	112.15 (10)	N3—C9—C8	121.03 (12)
C13—N4—H4	123.9	N3—C9—H9	119.5
N5—N4—H4	123.9	C8—C9—H9	119.5
C14—N5—N4	105.65 (12)	C11—C10—N3	115.26 (11)
N1—C1—C2	119.81 (11)	C11—C10—C16	119.99 (12)
N1—C1—C6	121.24 (11)	N3—C10—C16	124.73 (12)
C2—C1—C6	118.94 (12)	C10—C11—C12	119.44 (11)
C3—C2—C1	119.78 (13)	C10—C11—H11	120.3
C3—C2—H2	120.1	C12—C11—H11	120.3
C1—C2—H2	120.1	C11—C12—C13	119.28 (12)
C2—C3—C4	121.20 (13)	C11—C12—C14	136.49 (12)
C2—C3—H3	119.4	C13—C12—C14	104.21 (11)
C4—C3—H3	119.4	N4—C13—C15	131.95 (11)
C5—C4—C3	120.49 (14)	N4—C13—C12	106.21 (12)
C5—C4—H4A	119.8	C15—C13—C12	121.83 (12)
C3—C4—H4A	119.8	N5—C14—C12	111.77 (12)
C4—C5—C6	119.80 (13)	N5—C14—H14	124.1
C4—C5—H5	120.1	C12—C14—H14	124.1
C6—C5—H5	120.1	C16—C15—C13	117.81 (11)
N2—C6—C5	119.47 (11)	C16—C15—H15	121.1
N2—C6—C1	120.78 (12)	C13—C15—H15	121.1
C5—C6—C1	119.75 (12)	C15—C16—C10	121.58 (13)
N1—C7—C8	122.85 (13)	C15—C16—H16	119.2
N1—C7—H7	118.6	C10—C16—H16	119.2
C8—C7—H7	118.6

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1iii	0.86	2.31	3.1050 (15)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N1iii	0.86	2.31	3.1050 (15)	153

Symmetry code: (iii) .