4-Hydrazinyl-1-isobutyl-1H-imidazo[4,5-c]quinoline.

In the title compound, C(14)H(17)N(5), the 1H-imidazo[4,5-c]quinoline ring system is essentially planar, with a maximum deviation of 0.0325 (7) Å. In the crystal, a pair of inter-molecular N-H⋯N hydrogen bonds link neighbouring mol-ecules, forming an inversion dimer and generate an R(2) (2)(10) ring motif. These dimers are further connected into a chain along the b axis via inter-molecular C-H⋯N hydrogen bonds, resulting in an R(2) (2)(14) ring motif.

Related literature

For background to quinolines and their microbial activity, see: Roth & Fenner (2000 ▶); Miller et al. (1999 ▶); Hirota et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Loh et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H17N5

M = 255.33

Triclinic,

a = 5.4735 (2) Å

b = 9.1275 (3) Å

c = 13.3814 (5) Å

α = 98.076 (1)°

β = 101.787 (1)°

γ = 96.269 (1)°

V = 641.35 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.68 × 0.42 × 0.09 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.945, T max = 0.992

20646 measured reflections

5797 independent reflections

4836 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.137

S = 1.12

5797 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001553/is2657sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001553/is2657Isup2.hkl

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

C14H17N5	Z = 2
Mr = 255.33	F(000) = 272
Triclinic, P1	Dx = 1.322 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4735 (2) Å	Cell parameters from 9851 reflections
b = 9.1275 (3) Å	θ = 2.5–35.6°
c = 13.3814 (5) Å	µ = 0.08 mm−1
α = 98.076 (1)°	T = 100 K
β = 101.787 (1)°	Plate, yellow
γ = 96.269 (1)°	0.68 × 0.42 × 0.09 mm
V = 641.35 (4) Å3

Bruker SMART APEXII DUO CCD area-detector diffractometer	5797 independent reflections
Radiation source: fine-focus sealed tube	4836 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 35.6°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.945, Tmax = 0.992	k = −14→14
20646 measured reflections	l = −21→21

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0821P)2 + 0.0687P] where P = (Fo2 + 2Fc2)/3
5797 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
N3	0.66263 (12)	0.41343 (6)	0.40530 (5)	0.01739 (12)
N2	0.83913 (11)	0.28950 (6)	0.28779 (4)	0.01494 (11)
N1	0.29129 (11)	0.04458 (6)	0.39588 (4)	0.01382 (11)
N4	0.27467 (12)	0.27155 (7)	0.49606 (5)	0.01719 (12)
N5	0.09896 (12)	0.21044 (7)	0.54799 (5)	0.01683 (11)
C9	0.66447 (12)	0.18519 (7)	0.31040 (5)	0.01294 (11)
C1	0.58776 (12)	0.02794 (7)	0.27674 (5)	0.01284 (11)
C2	0.68633 (13)	−0.06582 (7)	0.20610 (5)	0.01545 (12)
C3	0.60210 (14)	−0.21733 (7)	0.18278 (5)	0.01727 (13)
C4	0.41445 (14)	−0.27919 (7)	0.22854 (6)	0.01769 (13)
C5	0.31322 (13)	−0.19005 (7)	0.29698 (5)	0.01611 (12)
C6	0.39780 (12)	−0.03437 (7)	0.32402 (5)	0.01301 (11)
C7	0.37122 (12)	0.18938 (7)	0.42576 (5)	0.01334 (11)
C8	0.55945 (13)	0.26428 (7)	0.38309 (5)	0.01385 (11)
C10	0.82902 (15)	0.42279 (7)	0.34703 (5)	0.01813 (13)
C11	1.00391 (12)	0.26889 (7)	0.21544 (5)	0.01498 (12)
C12	0.86854 (13)	0.26095 (7)	0.10230 (5)	0.01536 (12)
C13	1.04956 (16)	0.22187 (9)	0.03277 (6)	0.02337 (15)
C14	0.77216 (15)	0.40809 (8)	0.08500 (6)	0.02100 (14)
H12	0.714 (2)	0.1783 (13)	0.0858 (9)	0.022 (3)*
H5	0.188 (2)	−0.2330 (14)	0.3351 (9)	0.023 (3)*
H11A	1.082 (2)	0.1765 (14)	0.2249 (9)	0.021 (3)*
H11B	1.135 (2)	0.3583 (12)	0.2340 (8)	0.016 (2)*
H3	0.684 (3)	−0.2852 (15)	0.1362 (10)	0.030 (3)*
H14A	0.647 (2)	0.4297 (15)	0.1284 (10)	0.028 (3)*
H2	0.824 (3)	−0.0234 (15)	0.1744 (10)	0.028 (3)*
H14B	0.684 (2)	0.4015 (15)	0.0128 (10)	0.027 (3)*
H13A	1.198 (3)	0.3048 (16)	0.0476 (10)	0.035 (3)*
H13B	0.967 (3)	0.2083 (16)	−0.0425 (11)	0.042 (4)*
H14C	0.914 (3)	0.4902 (15)	0.1002 (10)	0.027 (3)*
H2N5	−0.034 (3)	0.1553 (16)	0.5007 (11)	0.034 (3)*
H1N5	0.168 (2)	0.1427 (14)	0.5847 (9)	0.026 (3)*
H4	0.351 (3)	−0.3897 (15)	0.2119 (11)	0.033 (3)*
H1N4	0.338 (3)	0.3668 (17)	0.5163 (11)	0.039 (4)*
H10	0.947 (2)	0.5153 (13)	0.3482 (9)	0.023 (3)*
H13C	1.111 (3)	0.1258 (16)	0.0456 (11)	0.036 (3)*

	U11	U22	U33	U12	U13	U23
N3	0.0241 (3)	0.0107 (2)	0.0180 (2)	−0.00015 (19)	0.0094 (2)	−0.00037 (18)
N2	0.0186 (2)	0.0106 (2)	0.0163 (2)	−0.00019 (17)	0.00804 (18)	0.00044 (17)
N1	0.0166 (2)	0.0107 (2)	0.0146 (2)	0.00162 (17)	0.00618 (18)	−0.00006 (16)
N4	0.0236 (3)	0.0116 (2)	0.0184 (2)	0.00107 (19)	0.0123 (2)	−0.00060 (18)
N5	0.0190 (3)	0.0158 (2)	0.0174 (2)	0.00174 (19)	0.00878 (19)	0.00190 (18)
C9	0.0160 (3)	0.0101 (2)	0.0132 (2)	0.00083 (19)	0.00551 (19)	0.00118 (17)
C1	0.0152 (3)	0.0103 (2)	0.0134 (2)	0.00142 (18)	0.00501 (19)	0.00076 (18)
C2	0.0191 (3)	0.0117 (2)	0.0168 (3)	0.0018 (2)	0.0085 (2)	0.00019 (19)
C3	0.0211 (3)	0.0121 (2)	0.0196 (3)	0.0017 (2)	0.0096 (2)	−0.0009 (2)
C4	0.0209 (3)	0.0107 (2)	0.0215 (3)	0.0000 (2)	0.0091 (2)	−0.0015 (2)
C5	0.0180 (3)	0.0112 (2)	0.0195 (3)	−0.0001 (2)	0.0082 (2)	−0.0001 (2)
C6	0.0145 (2)	0.0109 (2)	0.0140 (2)	0.00148 (18)	0.00531 (19)	0.00056 (18)
C7	0.0164 (3)	0.0112 (2)	0.0131 (2)	0.00201 (19)	0.00547 (19)	0.00073 (18)
C8	0.0180 (3)	0.0106 (2)	0.0135 (2)	0.00126 (19)	0.00616 (19)	0.00052 (18)
C10	0.0244 (3)	0.0108 (2)	0.0195 (3)	−0.0011 (2)	0.0096 (2)	−0.0006 (2)
C11	0.0157 (3)	0.0136 (2)	0.0166 (2)	0.0008 (2)	0.0067 (2)	0.00201 (19)
C12	0.0174 (3)	0.0133 (2)	0.0162 (2)	0.0012 (2)	0.0064 (2)	0.00193 (19)
C13	0.0275 (4)	0.0252 (3)	0.0210 (3)	0.0058 (3)	0.0129 (3)	0.0032 (2)
C14	0.0244 (3)	0.0170 (3)	0.0226 (3)	0.0049 (2)	0.0055 (2)	0.0048 (2)

N3—C10	1.3179 (9)	C3—H3	1.020 (13)
N3—C8	1.3821 (8)	C4—C5	1.3798 (9)
N2—C10	1.3687 (9)	C4—H4	1.008 (14)
N2—C9	1.3828 (8)	C5—C6	1.4170 (9)
N2—C11	1.4590 (9)	C5—H5	1.011 (12)
N1—C7	1.3236 (8)	C7—C8	1.4322 (9)
N1—C6	1.3820 (8)	C10—H10	1.002 (12)
N4—C7	1.3484 (8)	C11—C12	1.5315 (9)
N4—N5	1.4085 (9)	C11—H11A	0.999 (12)
N4—H1N4	0.883 (15)	C11—H11B	0.993 (11)
N5—H2N5	0.909 (14)	C12—C14	1.5258 (10)
N5—H1N5	0.909 (13)	C12—C13	1.5282 (10)
C9—C8	1.3854 (9)	C12—H12	1.037 (12)
C9—C1	1.4314 (9)	C13—H13A	1.014 (14)
C1—C2	1.4138 (9)	C13—H13B	1.000 (14)
C1—C6	1.4302 (9)	C13—H13C	0.998 (14)
C2—C3	1.3795 (9)	C14—H14A	1.001 (13)
C2—H2	1.008 (14)	C14—H14B	0.978 (13)
C3—C4	1.4058 (10)	C14—H14C	0.985 (14)
C10—N3—C8	103.93 (5)	N1—C7—C8	121.10 (6)
C10—N2—C9	106.32 (6)	N4—C7—C8	117.90 (6)
C10—N2—C11	124.73 (6)	N3—C8—C9	111.27 (6)
C9—N2—C11	128.95 (5)	N3—C8—C7	128.47 (6)
C7—N1—C6	118.55 (6)	C9—C8—C7	120.25 (6)
C7—N4—N5	123.58 (6)	N3—C10—N2	113.44 (6)
C7—N4—H1N4	118.2 (10)	N3—C10—H10	124.7 (7)
N5—N4—H1N4	117.8 (10)	N2—C10—H10	121.7 (7)
N4—N5—H2N5	109.3 (9)	N2—C11—C12	113.35 (6)
N4—N5—H1N5	109.3 (8)	N2—C11—H11A	108.6 (7)
H2N5—N5—H1N5	104.1 (12)	C12—C11—H11A	110.6 (7)
N2—C9—C8	105.04 (5)	N2—C11—H11B	106.1 (6)
N2—C9—C1	134.08 (6)	C12—C11—H11B	107.6 (6)
C8—C9—C1	120.87 (6)	H11A—C11—H11B	110.5 (9)
C2—C1—C6	119.84 (6)	C14—C12—C13	111.16 (6)
C2—C1—C9	126.25 (6)	C14—C12—C11	110.90 (5)
C6—C1—C9	113.89 (6)	C13—C12—C11	108.94 (6)
C3—C2—C1	120.58 (6)	C14—C12—H12	107.7 (6)
C3—C2—H2	119.1 (7)	C13—C12—H12	110.1 (7)
C1—C2—H2	120.3 (7)	C11—C12—H12	108.0 (6)
C2—C3—C4	119.88 (6)	C12—C13—H13A	109.6 (8)
C2—C3—H3	120.0 (8)	C12—C13—H13B	112.4 (9)
C4—C3—H3	120.0 (8)	H13A—C13—H13B	108.1 (11)
C5—C4—C3	120.75 (6)	C12—C13—H13C	109.9 (8)
C5—C4—H4	118.6 (8)	H13A—C13—H13C	109.8 (12)
C3—C4—H4	120.6 (8)	H13B—C13—H13C	106.9 (12)
C4—C5—C6	120.97 (6)	C12—C14—H14A	110.3 (7)
C4—C5—H5	122.2 (7)	C12—C14—H14B	110.4 (8)
C6—C5—H5	116.6 (7)	H14A—C14—H14B	106.7 (10)
N1—C6—C5	116.69 (6)	C12—C14—H14C	110.4 (8)
N1—C6—C1	125.32 (6)	H14A—C14—H14C	111.1 (11)
C5—C6—C1	117.98 (6)	H14B—C14—H14C	107.9 (11)
N1—C7—N4	120.99 (6)
C10—N2—C9—C8	−0.05 (7)	C6—N1—C7—N4	−179.65 (6)
C11—N2—C9—C8	−179.38 (6)	C6—N1—C7—C8	1.52 (10)
C10—N2—C9—C1	−178.69 (7)	N5—N4—C7—N1	4.70 (11)
C11—N2—C9—C1	1.98 (12)	N5—N4—C7—C8	−176.43 (6)
N2—C9—C1—C2	0.80 (12)	C10—N3—C8—C9	−0.50 (8)
C8—C9—C1—C2	−177.67 (6)	C10—N3—C8—C7	178.70 (7)
N2—C9—C1—C6	178.97 (7)	N2—C9—C8—N3	0.34 (8)
C8—C9—C1—C6	0.50 (9)	C1—C9—C8—N3	179.20 (6)
C6—C1—C2—C3	−0.43 (10)	N2—C9—C8—C7	−178.94 (6)
C9—C1—C2—C3	177.64 (6)	C1—C9—C8—C7	−0.07 (10)
C1—C2—C3—C4	0.77 (11)	N1—C7—C8—N3	179.87 (6)
C2—C3—C4—C5	−0.14 (11)	N4—C7—C8—N3	1.00 (11)
C3—C4—C5—C6	−0.84 (11)	N1—C7—C8—C9	−0.99 (10)
C7—N1—C6—C5	177.81 (6)	N4—C7—C8—C9	−179.86 (6)
C7—N1—C6—C1	−1.08 (10)	C8—N3—C10—N2	0.48 (8)
C4—C5—C6—N1	−177.81 (6)	C9—N2—C10—N3	−0.28 (8)
C4—C5—C6—C1	1.16 (10)	C11—N2—C10—N3	179.09 (6)
C2—C1—C6—N1	178.35 (6)	C10—N2—C11—C12	−101.17 (8)
C9—C1—C6—N1	0.05 (10)	C9—N2—C11—C12	78.06 (8)
C2—C1—C6—C5	−0.52 (10)	N2—C11—C12—C14	63.65 (7)
C9—C1—C6—C5	−178.82 (6)	N2—C11—C12—C13	−173.69 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H1N4···N3i	0.883 (16)	2.130 (15)	2.9429 (9)	152.9 (15)
C5—H5···N5ii	1.012 (12)	2.437 (11)	3.3700 (10)	152.9 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H1N4⋯N3i	0.883 (16)	2.130 (15)	2.9429 (9)	152.9 (15)
C5—H5⋯N5ii	1.012 (12)	2.437 (11)	3.3700 (10)	152.9 (10)

Symmetry codes: (i) ; (ii) .