Methyl 3-(4-methyl-benzyl-idene)carbazate.

The title compound, C(10)H(12)N(2)O(2), was prepared by the reaction of methyl carbazate and 4-methyl-benzaldehyde. The dihedral angle between the benzene ring and the carbazate fragment is 20.86 (10)°. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For background to Schiff bases, see: Cimerman et al. (1997 ▶). For C=N bond lengths, see: Girgis (2006 ▶). For a related structure, see: Li et al. (2009 ▶).

Experimental

Crystal data

C10H12N2O2

M = 192.22

Monoclinic,

a = 10.038 (2) Å

b = 13.308 (3) Å

c = 7.7923 (16) Å

β = 99.71 (3)°

V = 1026.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

9493 measured reflections

2322 independent reflections

1528 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.175

S = 1.06

2322 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 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/S160053681001799X/hg2684sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001799X/hg2684Isup2.hkl

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

C10H12N2O2	F(000) = 408
Mr = 192.22	Dx = 1.244 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1798 reflections
a = 10.038 (2) Å	θ = 3.5–25.2°
b = 13.308 (3) Å	µ = 0.09 mm−1
c = 7.7923 (16) Å	T = 293 K
β = 99.71 (3)°	Blcok, colorless
V = 1026.1 (4) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1528 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
graphite	θmax = 27.5°, θmin = 3.1°
phi and ω scans	h = −13→12
9493 measured reflections	k = −17→17
2322 independent reflections	l = −9→10

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.1077P)2] where P = (Fo2 + 2Fc2)/3
2322 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.23 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
O2	0.44060 (12)	0.82548 (9)	0.19195 (16)	0.0656 (4)
C9	0.55062 (16)	0.81674 (12)	0.1159 (2)	0.0531 (4)
N2	0.75692 (13)	0.73089 (10)	0.14969 (17)	0.0559 (4)
O1	0.56744 (12)	0.86340 (9)	−0.01208 (15)	0.0636 (4)
C5	0.95735 (16)	0.62998 (12)	0.1941 (2)	0.0540 (4)
N1	0.63541 (14)	0.74964 (11)	0.20247 (18)	0.0617 (4)
H1A	0.6141	0.7184	0.2906	0.074*
C8	0.82561 (17)	0.66004 (13)	0.2311 (2)	0.0580 (4)
H8A	0.7903	0.6261	0.3176	0.070*
C3	1.15344 (17)	0.65532 (14)	0.0599 (2)	0.0661 (5)
H3A	1.2004	0.6951	−0.0078	0.079*
C2	1.20961 (17)	0.56483 (14)	0.1252 (2)	0.0623 (5)
C7	1.13692 (18)	0.50763 (15)	0.2245 (2)	0.0683 (5)
H7A	1.1719	0.4465	0.2692	0.082*
C6	1.01357 (17)	0.53927 (13)	0.2585 (2)	0.0629 (5)
H6A	0.9668	0.4992	0.3260	0.076*
C4	1.02987 (18)	0.68754 (13)	0.0931 (2)	0.0647 (5)
H4A	0.9947	0.7484	0.0475	0.078*
C10	0.3380 (2)	0.89244 (15)	0.1047 (3)	0.0789 (6)
H10A	0.2630	0.8938	0.1665	0.118*
H10B	0.3080	0.8693	−0.0120	0.118*
H10C	0.3749	0.9589	0.1017	0.118*
C1	1.3469 (2)	0.53239 (18)	0.0914 (3)	0.0857 (6)
H1B	1.3699	0.4687	0.1463	0.128*
H1C	1.4131	0.5815	0.1383	0.128*
H1D	1.3449	0.5263	−0.0317	0.128*

	U11	U22	U33	U12	U13	U23
O2	0.0612 (7)	0.0707 (8)	0.0700 (8)	0.0078 (5)	0.0254 (6)	0.0082 (6)
C9	0.0607 (10)	0.0489 (8)	0.0527 (9)	−0.0029 (7)	0.0181 (8)	−0.0056 (7)
N2	0.0573 (8)	0.0566 (8)	0.0561 (8)	0.0004 (6)	0.0165 (6)	−0.0012 (6)
O1	0.0813 (9)	0.0577 (7)	0.0566 (7)	0.0059 (6)	0.0251 (6)	0.0061 (5)
C5	0.0561 (9)	0.0530 (9)	0.0517 (9)	−0.0046 (7)	0.0059 (7)	−0.0048 (7)
N1	0.0632 (9)	0.0686 (9)	0.0580 (9)	0.0076 (7)	0.0241 (7)	0.0119 (7)
C8	0.0613 (10)	0.0600 (10)	0.0535 (9)	−0.0063 (8)	0.0121 (8)	0.0016 (7)
C3	0.0633 (10)	0.0656 (11)	0.0719 (12)	−0.0027 (8)	0.0187 (9)	0.0010 (8)
C2	0.0575 (9)	0.0670 (11)	0.0597 (10)	0.0026 (8)	0.0025 (8)	−0.0105 (8)
C7	0.0672 (11)	0.0635 (11)	0.0698 (11)	0.0086 (8)	−0.0011 (9)	0.0068 (8)
C6	0.0629 (10)	0.0635 (10)	0.0606 (10)	−0.0035 (8)	0.0052 (8)	0.0096 (8)
C4	0.0675 (11)	0.0547 (9)	0.0736 (12)	0.0034 (8)	0.0169 (9)	0.0050 (8)
C10	0.0678 (12)	0.0721 (12)	0.0987 (15)	0.0134 (9)	0.0196 (11)	0.0115 (11)
C1	0.0677 (12)	0.1015 (15)	0.0883 (14)	0.0137 (11)	0.0145 (10)	−0.0081 (12)

O2—C9	1.343 (2)	C3—H3A	0.9300
O2—C10	1.442 (2)	C2—C7	1.379 (3)
C9—O1	1.2108 (19)	C2—C1	1.509 (3)
C9—N1	1.335 (2)	C7—C6	1.375 (2)
N2—C8	1.273 (2)	C7—H7A	0.9300
N2—N1	1.3742 (19)	C6—H6A	0.9300
C5—C4	1.389 (2)	C4—H4A	0.9300
C5—C6	1.390 (2)	C10—H10A	0.9600
C5—C8	1.456 (2)	C10—H10B	0.9600
N1—H1A	0.8600	C10—H10C	0.9600
C8—H8A	0.9300	C1—H1B	0.9600
C3—C4	1.378 (2)	C1—H1C	0.9600
C3—C2	1.389 (3)	C1—H1D	0.9600
C9—O2—C10	114.86 (13)	C6—C7—H7A	119.4
O1—C9—N1	126.40 (15)	C2—C7—H7A	119.4
O1—C9—O2	123.93 (15)	C7—C6—C5	121.34 (17)
N1—C9—O2	109.67 (14)	C7—C6—H6A	119.3
C8—N2—N1	114.77 (14)	C5—C6—H6A	119.3
C4—C5—C6	117.63 (16)	C3—C4—C5	120.62 (17)
C4—C5—C8	122.74 (16)	C3—C4—H4A	119.7
C6—C5—C8	119.61 (16)	C5—C4—H4A	119.7
C9—N1—N2	119.52 (13)	O2—C10—H10A	109.5
C9—N1—H1A	120.2	O2—C10—H10B	109.5
N2—N1—H1A	120.2	H10A—C10—H10B	109.5
N2—C8—C5	122.59 (16)	O2—C10—H10C	109.5
N2—C8—H8A	118.7	H10A—C10—H10C	109.5
C5—C8—H8A	118.7	H10B—C10—H10C	109.5
C4—C3—C2	121.59 (17)	C2—C1—H1B	109.5
C4—C3—H3A	119.2	C2—C1—H1C	109.5
C2—C3—H3A	119.2	H1B—C1—H1C	109.5
C7—C2—C3	117.61 (17)	C2—C1—H1D	109.5
C7—C2—C1	121.67 (17)	H1B—C1—H1D	109.5
C3—C2—C1	120.70 (18)	H1C—C1—H1D	109.5
C6—C7—C2	121.21 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.00	2.8615 (18)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.00	2.8615 (18)	176

Symmetry code: (i) .