2-[(E)-3,4-Dimeth-oxy-benzyl-idene]hydrazinecarboxamide.

In the title compound, C(10)H(13)N(3)O(3), the 3,4-dimeth-oxy-benzyl-idene and hydrazinecarboxamide groups are oriented at a dihedral angle of 53.82 (6)° and an intra-molecular N-H⋯N hydrogen bond generates an S(5) ring motif. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into sheets propagating in (-201), which feature R(1) (2)(5), R(2) (2)(8) and R(2) (4)(14) loops.

Related literature

For related structures, see: Fun et al. (2011 ▶); Liang et al. (2007 ▶); For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H13N3O3

M = 223.23

Monoclinic,

a = 22.2300 (7) Å

b = 7.6367 (3) Å

c = 15.6482 (6) Å

β = 126.234 (1)°

V = 2142.76 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.25 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.985

7933 measured reflections

2115 independent reflections

1389 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.121

S = 1.01

2115 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020739/hb6783sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020739/hb6783Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020739/hb6783Isup3.cml

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

C10H13N3O3	F(000) = 944
Mr = 223.23	Dx = 1.384 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1389 reflections
a = 22.2300 (7) Å	θ = 2.3–26.0°
b = 7.6367 (3) Å	µ = 0.10 mm−1
c = 15.6482 (6) Å	T = 296 K
β = 126.234 (1)°	Prism, yellow
V = 2142.76 (14) Å3	0.25 × 0.18 × 0.15 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	2115 independent reflections
Radiation source: fine-focus sealed tube	1389 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 2.3°
ω scans	h = −26→27
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.975, Tmax = 0.985	l = −19→19
7933 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.0283P] where P = (Fo2 + 2Fc2)/3
2115 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.30582 (7)	−0.13305 (19)	0.72476 (10)	0.0464 (5)
O2	0.34785 (7)	0.03543 (19)	0.62646 (10)	0.0454 (5)
O3	−0.01303 (7)	0.24827 (17)	−0.02345 (10)	0.0447 (5)
N1	0.10093 (8)	0.0967 (2)	0.23838 (12)	0.0404 (5)
N2	0.04892 (8)	0.0982 (2)	0.12929 (12)	0.0421 (5)
N3	0.06302 (9)	0.3952 (2)	0.13090 (13)	0.0445 (6)
C1	0.15297 (10)	−0.0591 (2)	0.40077 (15)	0.0347 (6)
C2	0.22548 (10)	0.0085 (2)	0.45703 (15)	0.0356 (6)
C3	0.27503 (10)	−0.0179 (2)	0.56479 (14)	0.0331 (6)
C4	0.25221 (10)	−0.1097 (2)	0.61917 (15)	0.0345 (6)
C5	0.18023 (10)	−0.1725 (3)	0.56366 (15)	0.0394 (7)
C6	0.13153 (10)	−0.1495 (3)	0.45538 (15)	0.0397 (7)
C7	0.28984 (13)	−0.2490 (3)	0.78007 (16)	0.0527 (8)
C8	0.37782 (11)	0.1099 (3)	0.57544 (17)	0.0490 (8)
C9	0.10014 (10)	−0.0369 (3)	0.28603 (15)	0.0400 (7)
C10	0.03155 (9)	0.2502 (3)	0.07501 (15)	0.0347 (6)
H2	0.24028	0.07157	0.42152	0.0427*
H2A	0.02764	0.00235	0.09601	0.0505*
H3A	0.05296	0.49443	0.09922	0.0534*
H3B	0.09351	0.38993	0.19885	0.0534*
H5	0.16442	−0.23070	0.59936	0.0473*
H6	0.08359	−0.19543	0.41857	0.0476*
H7A	0.24962	−0.20238	0.77979	0.0791*
H7B	0.33332	−0.26156	0.85185	0.0791*
H7C	0.27580	−0.36131	0.74591	0.0791*
H8A	0.35195	0.21675	0.54077	0.0735*
H8B	0.37181	0.02896	0.52397	0.0735*
H8C	0.42987	0.13423	0.62723	0.0735*
H9	0.06472	−0.12360	0.24658	0.0479*

	U11	U22	U33	U12	U13	U23
O1	0.0482 (8)	0.0532 (9)	0.0289 (8)	−0.0080 (7)	0.0179 (7)	0.0017 (7)
O2	0.0369 (8)	0.0576 (9)	0.0338 (8)	−0.0152 (7)	0.0165 (7)	−0.0050 (7)
O3	0.0471 (8)	0.0416 (9)	0.0264 (7)	0.0006 (6)	0.0113 (7)	−0.0004 (6)
N1	0.0408 (9)	0.0384 (10)	0.0272 (9)	0.0008 (7)	0.0120 (8)	−0.0009 (7)
N2	0.0448 (10)	0.0355 (9)	0.0263 (9)	−0.0042 (8)	0.0102 (8)	−0.0018 (7)
N3	0.0476 (10)	0.0351 (10)	0.0320 (10)	−0.0030 (8)	0.0132 (8)	−0.0010 (7)
C1	0.0362 (10)	0.0307 (10)	0.0330 (11)	0.0031 (8)	0.0181 (9)	−0.0009 (8)
C2	0.0401 (11)	0.0327 (11)	0.0345 (11)	−0.0023 (8)	0.0224 (9)	−0.0013 (8)
C3	0.0321 (10)	0.0330 (10)	0.0303 (11)	−0.0042 (8)	0.0163 (9)	−0.0062 (8)
C4	0.0374 (10)	0.0335 (10)	0.0304 (10)	0.0001 (8)	0.0188 (9)	−0.0022 (8)
C5	0.0417 (11)	0.0418 (12)	0.0394 (12)	−0.0001 (9)	0.0266 (10)	0.0031 (9)
C6	0.0307 (10)	0.0406 (12)	0.0421 (12)	0.0005 (9)	0.0184 (9)	0.0015 (9)
C7	0.0604 (14)	0.0619 (16)	0.0364 (12)	−0.0022 (11)	0.0289 (11)	0.0071 (11)
C8	0.0462 (12)	0.0524 (14)	0.0524 (14)	−0.0126 (10)	0.0313 (12)	−0.0047 (11)
C9	0.0350 (11)	0.0397 (12)	0.0337 (11)	−0.0015 (9)	0.0140 (10)	−0.0014 (9)
C10	0.0289 (10)	0.0391 (11)	0.0294 (10)	−0.0001 (8)	0.0136 (9)	−0.0010 (9)

O1—C4	1.362 (2)	C2—C3	1.379 (3)
O1—C7	1.422 (3)	C3—C4	1.408 (3)
O2—C3	1.368 (3)	C4—C5	1.379 (3)
O2—C8	1.426 (3)	C5—C6	1.380 (3)
O3—C10	1.245 (2)	C2—H2	0.9300
N1—N2	1.385 (2)	C5—H5	0.9300
N1—C9	1.270 (3)	C6—H6	0.9300
N2—C10	1.353 (3)	C7—H7A	0.9600
N3—C10	1.326 (3)	C7—H7B	0.9600
N2—H2A	0.8600	C7—H7C	0.9600
N3—H3A	0.8600	C8—H8A	0.9600
N3—H3B	0.8600	C8—H8B	0.9600
C1—C9	1.463 (3)	C8—H8C	0.9600
C1—C2	1.401 (3)	C9—H9	0.9300
C1—C6	1.384 (3)
C4—O1—C7	117.75 (18)	N2—C10—N3	117.33 (17)
C3—O2—C8	118.26 (15)	O3—C10—N2	119.32 (19)
N2—N1—C9	116.05 (17)	C1—C2—H2	120.00
N1—N2—C10	120.10 (15)	C3—C2—H2	120.00
N1—N2—H2A	120.00	C4—C5—H5	120.00
C10—N2—H2A	120.00	C6—C5—H5	120.00
C10—N3—H3A	120.00	C1—C6—H6	120.00
C10—N3—H3B	120.00	C5—C6—H6	120.00
H3A—N3—H3B	120.00	O1—C7—H7A	109.00
C2—C1—C6	118.95 (18)	O1—C7—H7B	109.00
C2—C1—C9	121.3 (2)	O1—C7—H7C	109.00
C6—C1—C9	119.7 (2)	H7A—C7—H7B	109.00
C1—C2—C3	120.4 (2)	H7A—C7—H7C	109.00
C2—C3—C4	119.9 (2)	H7B—C7—H7C	109.00
O2—C3—C4	114.88 (16)	O2—C8—H8A	109.00
O2—C3—C2	125.2 (2)	O2—C8—H8B	109.00
O1—C4—C5	125.2 (2)	O2—C8—H8C	109.00
O1—C4—C3	115.4 (2)	H8A—C8—H8B	109.00
C3—C4—C5	119.39 (18)	H8A—C8—H8C	109.00
C4—C5—C6	120.3 (2)	H8B—C8—H8C	109.00
C1—C6—C5	121.0 (2)	N1—C9—H9	119.00
N1—C9—C1	122.29 (19)	C1—C9—H9	119.00
O3—C10—N3	123.4 (2)
C7—O1—C4—C3	−169.75 (18)	C2—C1—C9—N1	−31.7 (3)
C7—O1—C4—C5	8.3 (3)	C6—C1—C9—N1	148.8 (2)
C8—O2—C3—C2	−6.2 (3)	C1—C2—C3—O2	176.97 (18)
C8—O2—C3—C4	172.38 (17)	C1—C2—C3—C4	−1.5 (3)
C9—N1—N2—C10	162.2 (2)	O2—C3—C4—O1	−0.4 (2)
N2—N1—C9—C1	178.4 (2)	O2—C3—C4—C5	−178.58 (18)
N1—N2—C10—O3	177.1 (2)	C2—C3—C4—O1	178.23 (17)
N1—N2—C10—N3	−3.6 (3)	C2—C3—C4—C5	0.1 (3)
C6—C1—C2—C3	1.3 (3)	O1—C4—C5—C6	−176.4 (2)
C9—C1—C2—C3	−178.29 (19)	C3—C4—C5—C6	1.6 (3)
C2—C1—C6—C5	0.4 (3)	C4—C5—C6—C1	−1.9 (3)
C9—C1—C6—C5	180.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.86	2.15	2.970 (2)	159
N3—H3A···O3ii	0.86	2.19	3.044 (2)	170
N3—H3B···N1	0.86	2.30	2.657 (2)	105
N3—H3B···O1iii	0.86	2.59	3.019 (2)	112
N3—H3B···O2iii	0.86	2.30	3.119 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.86	2.15	2.970 (2)	159
N3—H3A⋯O3ii	0.86	2.19	3.044 (2)	170
N3—H3B⋯N1	0.86	2.30	2.657 (2)	105
N3—H3B⋯O1iii	0.86	2.59	3.019 (2)	112
N3—H3B⋯O2iii	0.86	2.30	3.119 (2)	160

Symmetry codes: (i) ; (ii) ; (iii) .