3-(1,3-Dioxolan-2-yl)-2-hydrazino-7-methyl-quinoline.

In the title mol-ecule, C(13)H(15)N(3)O(2), the dihedral angle between the mean plane of the 1,3-dioxolane group and the 2-hydrazino-7-methyl-isoquinoline unit is 85.21 (5)°. The conformation of the mol-ecule is influenced by bifurcated N-H⋯(O,O) and N-H⋯N intra-molecular hydrogen bonds. In the crystal structure, mol-ecules are linked via inter-molecular N-H⋯O hydrogen bonds, forming extended chains along [001].

Related literature

For general background to hydrazine compounds, see: Broadhurst et al. (2001 ▶); Behrens (1999 ▶); Broadhurst (1991 ▶); Chao et al. (1999 ▶); Kametani (1968 ▶). For related crystal structures, see: Yang et al. (2008 ▶); Choudhury & Guru Row (2006 ▶); Choudhury et al. (2002 ▶); Hathwar et al. (2008 ▶); Cho et al. (2002 ▶); Manivel et al. (2009 ▶), and references therein. For bond-length data, see: Allen et al., 1987 ▶)

Experimental

Crystal data

C13H15N3O2

M = 245.28

Monoclinic,

a = 13.1909 (17) Å

b = 10.1165 (13) Å

c = 9.7805 (13) Å

β = 109.956 (2)°

V = 1226.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 290 (2) K

0.30 × 0.21 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 0.987

8929 measured reflections

2279 independent reflections

1699 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.129

S = 1.06

2279 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003031/lh2748sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003031/lh2748Isup2.hkl

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

C13H15N3O2	F(000) = 520
Mr = 245.28	Dx = 1.328 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 948 reflections
a = 13.1909 (17) Å	θ = 1.8–24.6°
b = 10.1165 (13) Å	µ = 0.09 mm−1
c = 9.7805 (13) Å	T = 290 K
β = 109.956 (2)°	Block, brown
V = 1226.8 (3) Å3	0.30 × 0.21 × 0.14 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2279 independent reflections
Radiation source: fine-focus sealed tube	1699 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.942, Tmax = 0.987	k = −10→12
8929 measured reflections	l = −11→11

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.072P)2 + 0.1104P] where P = (Fo2 + 2Fc2)/3
2279 reflections	(Δ/σ)max < 0.001
176 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.10652 (9)	0.42297 (12)	−0.28334 (11)	0.0621 (4)
O2	0.09919 (10)	0.22186 (13)	−0.18872 (12)	0.0701 (4)
N1	0.32415 (10)	0.45872 (13)	0.15262 (13)	0.0524 (4)
N2	0.14264 (11)	0.45599 (16)	0.02767 (15)	0.0597 (4)
N3	0.12501 (13)	0.53613 (19)	0.13548 (18)	0.0664 (4)
C1	0.24495 (12)	0.42351 (15)	0.03448 (15)	0.0464 (4)
C2	0.26133 (12)	0.35152 (15)	−0.08326 (15)	0.0480 (4)
C3	0.36404 (13)	0.31857 (15)	−0.06896 (17)	0.0550 (4)
H3A	0.3772	0.2726	−0.1435	0.066*
C4	0.56033 (15)	0.32091 (18)	0.0793 (2)	0.0688 (5)
H4A	0.5778	0.2750	0.0080	0.083*
C5	0.64009 (14)	0.35734 (19)	0.2051 (2)	0.0732 (6)
H5A	0.7111	0.3344	0.2186	0.088*
C6	0.61719 (14)	0.4286 (2)	0.3145 (2)	0.0662 (5)
C7	0.51244 (13)	0.46184 (19)	0.29207 (17)	0.0615 (5)
H7A	0.4966	0.5107	0.3628	0.074*
C8	0.42773 (12)	0.42464 (15)	0.16556 (16)	0.0496 (4)
C9	0.45173 (12)	0.35270 (15)	0.05728 (17)	0.0533 (4)
C10	0.70689 (16)	0.4661 (3)	0.4525 (2)	0.0949 (8)
H10A	0.6767	0.4936	0.5244	0.142*
H10B	0.7481	0.5372	0.4329	0.142*
H10C	0.7530	0.3911	0.4882	0.142*
C11	0.17109 (13)	0.31376 (16)	−0.21833 (17)	0.0540 (4)
H11A	0.2010	0.2745	−0.2879	0.065*
C12	−0.00343 (14)	0.2421 (2)	−0.2979 (2)	0.0782 (6)
H12A	−0.0588	0.2540	−0.2544	0.094*
H12B	−0.0228	0.1675	−0.3640	0.094*
C13	0.00918 (15)	0.3653 (2)	−0.37670 (19)	0.0764 (6)
H13A	0.0146	0.3440	−0.4706	0.092*
H13B	−0.0513	0.4247	−0.3910	0.092*
H2N	0.0904 (15)	0.4447 (17)	−0.050 (2)	0.064 (5)*
H3NB	0.1453 (18)	0.484 (2)	0.218 (2)	0.095 (7)*
H3NA	0.1821 (17)	0.597 (2)	0.158 (2)	0.078 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0577 (7)	0.0724 (8)	0.0494 (6)	0.0026 (6)	0.0095 (5)	0.0034 (5)
O2	0.0667 (8)	0.0722 (8)	0.0642 (7)	−0.0201 (6)	0.0130 (6)	−0.0040 (6)
N1	0.0475 (8)	0.0647 (9)	0.0438 (7)	−0.0047 (6)	0.0141 (6)	−0.0015 (6)
N2	0.0476 (8)	0.0838 (11)	0.0443 (7)	0.0051 (7)	0.0114 (6)	−0.0113 (7)
N3	0.0626 (10)	0.0782 (11)	0.0586 (9)	0.0087 (9)	0.0211 (7)	−0.0131 (9)
C1	0.0467 (8)	0.0495 (9)	0.0426 (8)	0.0001 (7)	0.0145 (7)	0.0037 (6)
C2	0.0497 (9)	0.0465 (8)	0.0470 (8)	0.0006 (7)	0.0153 (7)	0.0012 (6)
C3	0.0580 (10)	0.0492 (9)	0.0589 (9)	0.0019 (7)	0.0214 (8)	−0.0077 (7)
C4	0.0566 (10)	0.0607 (11)	0.0890 (13)	0.0055 (8)	0.0245 (9)	−0.0053 (10)
C5	0.0424 (9)	0.0707 (12)	0.0974 (14)	0.0022 (8)	0.0122 (9)	0.0105 (11)
C6	0.0518 (10)	0.0774 (13)	0.0628 (11)	−0.0136 (9)	0.0108 (8)	0.0122 (9)
C7	0.0526 (10)	0.0785 (12)	0.0512 (9)	−0.0134 (8)	0.0148 (8)	0.0024 (8)
C8	0.0480 (9)	0.0526 (9)	0.0470 (8)	−0.0057 (7)	0.0147 (7)	0.0065 (7)
C9	0.0474 (9)	0.0470 (9)	0.0629 (10)	0.0001 (7)	0.0156 (7)	0.0035 (7)
C10	0.0550 (11)	0.138 (2)	0.0771 (13)	−0.0265 (12)	0.0040 (10)	0.0078 (13)
C11	0.0531 (9)	0.0597 (10)	0.0492 (9)	−0.0007 (7)	0.0175 (7)	−0.0083 (7)
C12	0.0554 (11)	0.0901 (15)	0.0852 (13)	−0.0112 (10)	0.0188 (10)	−0.0274 (12)
C13	0.0565 (11)	0.1135 (17)	0.0500 (9)	0.0012 (11)	0.0065 (8)	−0.0119 (11)

O1—C11	1.4074 (19)	C4—H4A	0.9300
O1—C13	1.422 (2)	C5—C6	1.406 (3)
O2—C12	1.424 (2)	C5—H5A	0.9300
O2—C11	1.427 (2)	C6—C7	1.365 (3)
N1—C1	1.3151 (18)	C6—C10	1.509 (2)
N1—C8	1.372 (2)	C7—C8	1.406 (2)
N2—C1	1.3683 (19)	C7—H7A	0.9300
N2—N3	1.411 (2)	C8—C9	1.407 (2)
N2—H2N	0.843 (19)	C10—H10A	0.9600
N3—H3NB	0.92 (2)	C10—H10B	0.9600
N3—H3NA	0.94 (2)	C10—H10C	0.9600
C1—C2	1.440 (2)	C11—H11A	0.9800
C2—C3	1.355 (2)	C12—C13	1.504 (3)
C2—C11	1.495 (2)	C12—H12A	0.9700
C3—C9	1.417 (2)	C12—H12B	0.9700
C3—H3A	0.9300	C13—H13A	0.9700
C4—C5	1.368 (3)	C13—H13B	0.9700
C4—C9	1.411 (2)
C11—O1—C13	104.05 (14)	N1—C8—C7	118.75 (15)
C12—O2—C11	106.35 (14)	N1—C8—C9	122.22 (14)
C1—N1—C8	118.70 (13)	C7—C8—C9	119.03 (15)
C1—N2—N3	120.87 (13)	C8—C9—C4	118.70 (15)
C1—N2—H2N	120.1 (12)	C8—C9—C3	117.09 (14)
N3—N2—H2N	117.4 (12)	C4—C9—C3	124.20 (16)
N2—N3—H3NB	104.8 (14)	C6—C10—H10A	109.5
N2—N3—H3NA	102.9 (12)	C6—C10—H10B	109.5
H3NB—N3—H3NA	101.6 (18)	H10A—C10—H10B	109.5
N1—C1—N2	116.89 (14)	C6—C10—H10C	109.5
N1—C1—C2	123.28 (14)	H10A—C10—H10C	109.5
N2—C1—C2	119.82 (13)	H10B—C10—H10C	109.5
C3—C2—C1	117.35 (13)	O1—C11—O2	105.16 (13)
C3—C2—C11	119.66 (14)	O1—C11—C2	112.04 (13)
C1—C2—C11	122.99 (13)	O2—C11—C2	111.79 (13)
C2—C3—C9	121.34 (15)	O1—C11—H11A	109.2
C2—C3—H3A	119.3	O2—C11—H11A	109.2
C9—C3—H3A	119.3	C2—C11—H11A	109.2
C5—C4—C9	120.33 (18)	O2—C12—C13	105.10 (14)
C5—C4—H4A	119.8	O2—C12—H12A	110.7
C9—C4—H4A	119.8	C13—C12—H12A	110.7
C4—C5—C6	121.55 (17)	O2—C12—H12B	110.7
C4—C5—H5A	119.2	C13—C12—H12B	110.7
C6—C5—H5A	119.2	H12A—C12—H12B	108.8
C7—C6—C5	118.21 (16)	O1—C13—C12	104.14 (14)
C7—C6—C10	121.57 (19)	O1—C13—H13A	110.9
C5—C6—C10	120.22 (17)	C12—C13—H13A	110.9
C6—C7—C8	122.15 (17)	O1—C13—H13B	110.9
C6—C7—H7A	118.9	C12—C13—H13B	110.9
C8—C7—H7A	118.9	H13A—C13—H13B	108.9

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.843 (19)	2.372 (18)	2.9329 (17)	124.5 (15)
N2—H2N···O2	0.843 (19)	2.653 (18)	3.0968 (19)	114.3 (14)
N3—H3NA···N1	0.94 (2)	2.35 (2)	2.691 (2)	100.9 (15)
N3—H3NB···O2i	0.92 (2)	2.44 (2)	3.207 (2)	141.2 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1	0.843 (19)	2.372 (18)	2.9329 (17)	124.5 (15)
N2—H2N⋯O2	0.843 (19)	2.653 (18)	3.0968 (19)	114.3 (14)
N3—H3NA⋯N1	0.94 (2)	2.35 (2)	2.691 (2)	100.9 (15)
N3—H3NB⋯O2i	0.92 (2)	2.44 (2)	3.207 (2)	141.2 (19)

Symmetry code: (i) .