Methyl 3-(3-pyridylmethyl-ene)carbazate.

In the crystal of the title compound, C(8)H(9)N(3)O(2), mol-ecules are linked by N-H⋯N hydrogen bonds, forming S(7) chains propagating in [010].

Related literature

For background to Schiff bases, see: Cimerman et al. (1997 ▶).

Experimental

Crystal data

C8H9N3O2

M = 179.18

Orthorhombic,

a = 10.585 (2) Å

b = 10.019 (2) Å

c = 16.311 (3) Å

V = 1729.8 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.26 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

15411 measured reflections

1984 independent reflections

1794 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.128

S = 1.08

1984 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045024/hb5196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045024/hb5196Isup2.hkl

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

C8H9N3O2	Dx = 1.376 Mg m−3
Mr = 179.18	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1985 reflections
a = 10.585 (2) Å	θ = 3.4–27.5°
b = 10.019 (2) Å	µ = 0.10 mm−1
c = 16.311 (3) Å	T = 293 K
V = 1729.8 (6) Å3	Block, colourless
Z = 8	0.26 × 0.21 × 0.19 mm
F(000) = 752

Bruker SMART CCD diffractometer	1794 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 27.5°, θmin = 3.1°
ω scans	h = −13→13
15411 measured reflections	k = −13→12
1984 independent 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0867P)2 + 0.1822P] where P = (Fo2 + 2Fc2)/3
1984 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.32 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
O2	0.18815 (8)	0.11348 (8)	0.57072 (5)	0.0433 (2)
C3	0.35300 (9)	−0.17778 (10)	0.74434 (7)	0.0343 (3)
H3A	0.4286	−0.1375	0.7291	0.041*
N4	0.48145 (8)	−0.43908 (10)	0.88319 (6)	0.0390 (3)
C5	0.35393 (9)	−0.28611 (10)	0.80449 (6)	0.0311 (2)
N1	0.26042 (8)	−0.03820 (9)	0.65555 (6)	0.0372 (2)
H1A	0.3336	−0.0124	0.6391	0.045*
C4	0.24493 (9)	−0.34567 (12)	0.83549 (7)	0.0377 (3)
H4B	0.1656	−0.3156	0.8194	0.045*
N2	0.24948 (8)	−0.13809 (9)	0.71265 (5)	0.0345 (2)
C2	0.15392 (9)	0.01936 (10)	0.62537 (6)	0.0339 (3)
O1	0.04701 (7)	−0.00686 (10)	0.64392 (6)	0.0541 (3)
C6	0.46946 (9)	−0.33613 (11)	0.83129 (6)	0.0358 (3)
H6A	0.5428	−0.2957	0.8120	0.043*
C8	0.37535 (11)	−0.49405 (11)	0.91219 (7)	0.0393 (3)
H8A	0.3819	−0.5651	0.9486	0.047*
C7	0.25615 (10)	−0.44962 (12)	0.89025 (7)	0.0414 (3)
H7A	0.1845	−0.4896	0.9123	0.050*
C1	0.08717 (14)	0.19038 (13)	0.53648 (8)	0.0523 (3)
H1B	0.1209	0.2546	0.4987	0.078*
H1C	0.0430	0.2359	0.5796	0.078*
H1D	0.0298	0.1322	0.5082	0.078*

	U11	U22	U33	U12	U13	U23
O2	0.0420 (5)	0.0450 (5)	0.0429 (5)	0.0031 (3)	0.0027 (3)	0.0115 (3)
C3	0.0289 (5)	0.0385 (5)	0.0355 (5)	−0.0040 (4)	−0.0007 (4)	0.0006 (4)
N4	0.0315 (5)	0.0440 (5)	0.0415 (5)	0.0086 (4)	−0.0001 (4)	0.0016 (4)
C5	0.0289 (5)	0.0341 (5)	0.0302 (5)	−0.0005 (4)	−0.0009 (3)	−0.0034 (4)
N1	0.0277 (4)	0.0426 (5)	0.0413 (5)	−0.0042 (3)	−0.0005 (3)	0.0102 (4)
C4	0.0257 (5)	0.0467 (6)	0.0407 (6)	−0.0008 (4)	−0.0037 (4)	0.0042 (4)
N2	0.0325 (4)	0.0364 (5)	0.0346 (4)	−0.0039 (3)	−0.0018 (3)	0.0033 (3)
C2	0.0324 (5)	0.0363 (5)	0.0330 (5)	−0.0018 (4)	−0.0015 (4)	0.0005 (4)
O1	0.0284 (4)	0.0685 (6)	0.0656 (6)	−0.0020 (4)	−0.0018 (4)	0.0220 (5)
C6	0.0263 (5)	0.0430 (6)	0.0380 (5)	0.0009 (4)	0.0026 (4)	−0.0003 (4)
C8	0.0400 (6)	0.0373 (5)	0.0407 (5)	0.0030 (4)	−0.0004 (4)	0.0038 (4)
C7	0.0312 (5)	0.0465 (6)	0.0463 (6)	−0.0069 (4)	0.0005 (4)	0.0064 (5)
C1	0.0603 (8)	0.0478 (6)	0.0489 (7)	0.0117 (6)	−0.0049 (6)	0.0102 (5)

O2—C2	1.3472 (13)	N1—H1A	0.8600
O2—C1	1.4312 (15)	C4—C7	1.3771 (16)
C3—N2	1.2752 (13)	C4—H4B	0.9300
C3—C5	1.4631 (14)	C2—O1	1.2005 (13)
C3—H3A	0.9300	C6—H6A	0.9300
N4—C8	1.3373 (14)	C8—C7	1.3850 (15)
N4—C6	1.3403 (14)	C8—H8A	0.9300
C5—C6	1.3920 (13)	C7—H7A	0.9300
C5—C4	1.3940 (13)	C1—H1B	0.9600
N1—C2	1.3586 (13)	C1—H1C	0.9600
N1—N2	1.3719 (12)	C1—H1D	0.9600
C2—O2—C1	115.73 (9)	O2—C2—N1	108.28 (9)
N2—C3—C5	120.59 (9)	N4—C6—C5	123.96 (9)
N2—C3—H3A	119.7	N4—C6—H6A	118.0
C5—C3—H3A	119.7	C5—C6—H6A	118.0
C8—N4—C6	117.44 (9)	N4—C8—C7	122.77 (10)
C6—C5—C4	117.33 (9)	N4—C8—H8A	118.6
C6—C5—C3	118.92 (8)	C7—C8—H8A	118.6
C4—C5—C3	123.73 (8)	C4—C7—C8	119.29 (10)
C2—N1—N2	119.05 (8)	C4—C7—H7A	120.4
C2—N1—H1A	120.5	C8—C7—H7A	120.4
N2—N1—H1A	120.5	O2—C1—H1B	109.5
C7—C4—C5	119.18 (9)	O2—C1—H1C	109.5
C7—C4—H4B	120.4	H1B—C1—H1C	109.5
C5—C4—H4B	120.4	O2—C1—H1D	109.5
C3—N2—N1	115.47 (8)	H1B—C1—H1D	109.5
O1—C2—O2	124.99 (10)	H1C—C1—H1D	109.5
O1—C2—N1	126.73 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4i	0.86	2.12	2.9751 (14)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N4i	0.86	2.12	2.9751 (14)	171

Symmetry code: (i) .