N'-[4-(Dimethyl-amino)benzyl-idene]acetohydrazide.

The title compound, C(11)H(15)N(3)O, crystallizes with two independent mol-ecules per asymmetric unit which differ slightly in their side-chain orientations: the C=N-N-C torsion angle is -176.2 (3)° in one of the mol-ecules and -179.83 (3)° in the other. Each independent mol-ecule adopts a trans configuration with respect to the C=N bond. The two independent mol-ecules are related by a pseudo-inversion center and they exist as a N-H⋯O hydrogen-bonded dimer. The dimers are linked into zigzag chains along [100] by C-H⋯O hydrogen bonds.

Related literature

For general background to this type of compound, see: Cimerman et al. (1997 ▶); Offe et al. (1952 ▶); Richardson et al. (1988 ▶). For related structures, see: Li & Jian (2008 ▶); Shang et al. (2007 ▶); Tamboura et al. (2009 ▶).

Experimental

Crystal data

C11H15N3O

M = 205.26

Orthorhombic,

a = 8.619 (4) Å

b = 20.063 (3) Å

c = 26.231 (3) Å

V = 4536 (2) Å3

Z = 16

Mo Kα radiation

μ = 0.08 mm−1

T = 223 K

0.25 × 0.21 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.977, T max = 0.979

25277 measured reflections

3944 independent reflections

2266 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.260

S = 1.05

3944 reflections

278 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAIn class="Chemical">NT; 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 I, global. DOI: 10.1107/S1600536809032619/ci2860sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032619/ci2860Isup2.hkl

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

C11H15N3O	F(000) = 1760
Mr = 205.26	Dx = 1.202 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3944 reflections
a = 8.619 (4) Å	θ = 1.5–25.0°
b = 20.063 (3) Å	µ = 0.08 mm−1
c = 26.231 (3) Å	T = 223 K
V = 4536 (2) Å3	Block, colourless
Z = 16	0.25 × 0.21 × 0.19 mm

Bruker SMART CCD area-detector diffractometer	3944 independent reflections
Radiation source: fine-focus sealed tube	2266 reflections with I > 2σ(I)
graphite	Rint = 0.086
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→10
Tmin = 0.977, Tmax = 0.979	k = −23→23
25277 measured reflections	l = −30→27

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.081	H-atom parameters constrained
wR(F2) = 0.260	w = 1/[σ2(Fo2) + (0.1428P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.009
3944 reflections	Δρmax = 0.26 e Å−3
278 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0088 (18)

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 > 2sigma(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	0.0047 (3)	0.29181 (12)	−0.13459 (9)	0.0780 (8)
O2	0.1988 (3)	0.06574 (13)	0.42455 (9)	0.0870 (9)
C1	−0.2222 (5)	0.2853 (2)	0.26167 (14)	0.0876 (12)
H1A	−0.2352	0.2920	0.2977	0.131*
H1B	−0.1581	0.2469	0.2560	0.131*
H1C	−0.3217	0.2784	0.2461	0.131*
C2	−0.0788 (5)	0.3912 (2)	0.27440 (14)	0.0960 (13)
H2A	−0.1206	0.3847	0.3080	0.144*
H2B	−0.1011	0.4357	0.2631	0.144*
H2C	0.0314	0.3845	0.2752	0.144*
C3	−0.1822 (4)	0.30188 (16)	0.15390 (12)	0.0642 (9)
H3	−0.2554	0.2715	0.1657	0.077*
C4	−0.1112 (4)	0.34523 (16)	0.18857 (12)	0.0609 (9)
C5	−0.0040 (4)	0.38962 (16)	0.16863 (13)	0.0705 (10)
H5	0.0450	0.4197	0.1903	0.085*
C6	0.0317 (4)	0.39019 (17)	0.11734 (13)	0.0711 (10)
H6A	0.1039	0.4208	0.1053	0.085*
C7	−0.0365 (4)	0.34675 (16)	0.08350 (12)	0.0602 (9)
C8	−0.1463 (4)	0.30314 (16)	0.10280 (12)	0.0636 (9)
H8	−0.1968	0.2741	0.0807	0.076*
C9	0.0084 (4)	0.34839 (18)	0.03007 (12)	0.0678 (9)
H9	0.0781	0.3809	0.0194	0.081*
C10	−0.0398 (4)	0.27958 (17)	−0.09107 (14)	0.0675 (10)
C11	−0.1489 (5)	0.2237 (2)	−0.08028 (14)	0.0894 (12)
H11A	−0.1751	0.2236	−0.0447	0.134*
H11B	−0.1005	0.1821	−0.0890	0.134*
H11C	−0.2415	0.2292	−0.1002	0.134*
C12	0.0762 (5)	0.1252 (2)	0.01346 (13)	0.0932 (13)
H12A	0.1036	0.1176	−0.0215	0.140*
H12B	0.0797	0.1721	0.0206	0.140*
H12C	−0.0268	0.1087	0.0196	0.140*
C13	0.2661 (6)	0.0345 (2)	0.02456 (15)	0.0972 (14)
H13A	0.2679	0.0387	−0.0119	0.146*
H13B	0.2141	−0.0060	0.0338	0.146*
H13C	0.3705	0.0335	0.0373	0.146*
C14	0.1752 (4)	0.09738 (16)	0.09815 (12)	0.0606 (9)
C15	0.0720 (5)	0.14273 (16)	0.12098 (12)	0.0684 (10)
H15	0.0105	0.1699	0.1005	0.082*
C16	0.0610 (4)	0.14740 (16)	0.17306 (12)	0.0670 (9)
H16	−0.0087	0.1776	0.1871	0.080*
C17	0.1510 (4)	0.10824 (15)	0.20548 (11)	0.0579 (9)
C18	0.2550 (4)	0.06487 (16)	0.18297 (12)	0.0616 (9)
H18	0.3176	0.0384	0.2036	0.074*
C19	0.2681 (4)	0.05990 (15)	0.13102 (12)	0.0647 (9)
H19	0.3408	0.0308	0.1173	0.078*
C20	0.1307 (4)	0.11238 (16)	0.26024 (12)	0.0642 (9)
H20	0.0637	0.1445	0.2732	0.077*
C21	0.2309 (4)	0.05138 (18)	0.37994 (13)	0.0684 (10)
C22	0.3373 (4)	−0.00500 (18)	0.36685 (13)	0.0772 (11)
H22A	0.4084	0.0090	0.3408	0.116*
H22B	0.2775	−0.0421	0.3547	0.116*
H22C	0.3942	−0.0181	0.3967	0.116*
N1	−0.0433 (3)	0.30740 (14)	−0.00272 (10)	0.0689 (8)
N2	0.0109 (3)	0.31648 (14)	−0.05201 (10)	0.0716 (8)
H2	0.0794	0.3468	−0.0576	0.086*
N3	−0.1490 (4)	0.34348 (16)	0.23945 (10)	0.0791 (9)
N4	0.1849 (4)	0.09056 (14)	0.04632 (10)	0.0786 (9)
N5	0.1997 (3)	0.07432 (14)	0.29129 (10)	0.0647 (8)
N6	0.1681 (3)	0.08653 (14)	0.34201 (10)	0.0714 (8)
H6	0.1049	0.1182	0.3495	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0901 (19)	0.0899 (18)	0.0541 (16)	0.0010 (14)	0.0130 (13)	−0.0020 (12)
O2	0.105 (2)	0.107 (2)	0.0488 (15)	0.0166 (16)	0.0105 (14)	0.0072 (12)
C1	0.107 (3)	0.093 (3)	0.063 (2)	0.005 (2)	0.020 (2)	0.0040 (19)
C2	0.098 (3)	0.123 (3)	0.068 (3)	−0.004 (3)	−0.001 (2)	−0.026 (2)
C3	0.066 (2)	0.068 (2)	0.058 (2)	−0.0080 (17)	−0.0004 (17)	0.0067 (16)
C4	0.063 (2)	0.069 (2)	0.050 (2)	0.0069 (17)	−0.0043 (16)	0.0006 (16)
C5	0.079 (3)	0.069 (2)	0.064 (2)	−0.0082 (18)	−0.002 (2)	−0.0084 (17)
C6	0.080 (3)	0.067 (2)	0.067 (2)	−0.0102 (18)	0.003 (2)	0.0036 (17)
C7	0.066 (2)	0.0609 (19)	0.054 (2)	0.0026 (17)	−0.0044 (16)	0.0072 (15)
C8	0.072 (2)	0.068 (2)	0.051 (2)	−0.0029 (18)	−0.0065 (17)	0.0000 (15)
C9	0.078 (3)	0.071 (2)	0.054 (2)	0.0010 (18)	0.0016 (18)	0.0029 (17)
C10	0.069 (2)	0.077 (2)	0.057 (2)	0.0096 (19)	0.0052 (18)	0.0013 (18)
C11	0.098 (3)	0.097 (3)	0.073 (3)	−0.023 (2)	−0.006 (2)	0.006 (2)
C12	0.114 (3)	0.109 (3)	0.057 (2)	0.002 (3)	−0.010 (2)	0.010 (2)
C13	0.135 (4)	0.091 (3)	0.066 (3)	0.011 (3)	0.007 (2)	−0.010 (2)
C14	0.073 (2)	0.0649 (19)	0.0436 (19)	−0.0063 (18)	−0.0001 (17)	−0.0009 (15)
C15	0.088 (3)	0.063 (2)	0.054 (2)	0.0069 (19)	−0.0034 (18)	0.0038 (16)
C16	0.072 (2)	0.068 (2)	0.062 (2)	0.0115 (18)	0.0025 (18)	−0.0035 (16)
C17	0.067 (2)	0.0607 (19)	0.0461 (19)	−0.0017 (16)	0.0002 (16)	0.0010 (14)
C18	0.068 (2)	0.0658 (19)	0.052 (2)	0.0061 (16)	−0.0032 (17)	0.0034 (15)
C19	0.079 (2)	0.0608 (19)	0.054 (2)	0.0037 (17)	0.0038 (18)	−0.0007 (15)
C20	0.067 (2)	0.072 (2)	0.054 (2)	0.0025 (18)	0.0035 (17)	−0.0050 (17)
C21	0.071 (2)	0.087 (2)	0.047 (2)	−0.0010 (19)	0.0036 (18)	0.0094 (18)
C22	0.080 (3)	0.083 (2)	0.068 (2)	0.004 (2)	0.0007 (19)	0.0059 (18)
N1	0.076 (2)	0.0802 (19)	0.0506 (17)	0.0032 (15)	0.0036 (14)	0.0104 (14)
N2	0.082 (2)	0.0794 (18)	0.0530 (18)	−0.0102 (16)	0.0073 (15)	0.0002 (14)
N3	0.095 (2)	0.092 (2)	0.0505 (18)	−0.0090 (18)	0.0027 (16)	−0.0076 (15)
N4	0.105 (3)	0.083 (2)	0.0478 (18)	0.0107 (17)	0.0013 (16)	0.0013 (14)
N5	0.0686 (19)	0.0819 (18)	0.0435 (16)	0.0004 (15)	0.0037 (14)	0.0026 (13)
N6	0.077 (2)	0.091 (2)	0.0465 (17)	0.0135 (16)	0.0070 (15)	0.0007 (14)

O1—C10	1.229 (4)	C12—H12A	0.96
O2—C21	1.236 (4)	C12—H12B	0.96
C1—N3	1.449 (5)	C12—H12C	0.96
C1—H1A	0.96	C13—N4	1.443 (5)
C1—H1B	0.96	C13—H13A	0.96
C1—H1C	0.96	C13—H13B	0.96
C2—N3	1.456 (5)	C13—H13C	0.96
C2—H2A	0.96	C14—N4	1.369 (4)
C2—H2B	0.96	C14—C19	1.396 (5)
C2—H2C	0.96	C14—C15	1.406 (5)
C3—C8	1.376 (4)	C15—C16	1.373 (4)
C3—C4	1.399 (4)	C15—H15	0.93
C3—H3	0.93	C16—C17	1.394 (4)
C4—N3	1.374 (4)	C16—H16	0.93
C4—C5	1.386 (5)	C17—C18	1.381 (4)
C5—C6	1.380 (4)	C17—C20	1.450 (4)
C5—H5	0.93	C18—C19	1.371 (4)
C6—C7	1.376 (5)	C18—H18	0.93
C6—H6A	0.93	C19—H19	0.93
C7—C8	1.384 (5)	C20—N5	1.265 (4)
C7—C9	1.454 (4)	C20—H20	0.93
C8—H8	0.93	C21—N6	1.334 (4)
C9—N1	1.271 (4)	C21—C22	1.496 (5)
C9—H9	0.93	C22—H22A	0.96
C10—N2	1.337 (4)	C22—H22B	0.96
C10—C11	1.491 (5)	C22—H22C	0.96
C11—H11A	0.96	N1—N2	1.387 (3)
C11—H11B	0.96	N2—H2	0.86
C11—H11C	0.96	N5—N6	1.380 (4)
C12—N4	1.450 (5)	N6—H6	0.86
N3—C1—H1A	109.5	N4—C13—H13B	109.5
N3—C1—H1B	109.5	H13A—C13—H13B	109.5
H1A—C1—H1B	109.5	N4—C13—H13C	109.4
N3—C1—H1C	109.5	H13A—C13—H13C	109.5
H1A—C1—H1C	109.5	H13B—C13—H13C	109.5
H1B—C1—H1C	109.5	N4—C14—C19	121.6 (3)
N3—C2—H2A	109.5	N4—C14—C15	121.7 (3)
N3—C2—H2B	109.5	C19—C14—C15	116.6 (3)
H2A—C2—H2B	109.5	C16—C15—C14	120.8 (3)
N3—C2—H2C	109.5	C16—C15—H15	119.6
H2A—C2—H2C	109.5	C14—C15—H15	119.6
H2B—C2—H2C	109.5	C15—C16—C17	122.0 (3)
C8—C3—C4	121.5 (3)	C15—C16—H16	119.0
C8—C3—H3	119.2	C17—C16—H16	119.0
C4—C3—H3	119.2	C18—C17—C16	117.1 (3)
N3—C4—C5	122.8 (3)	C18—C17—C20	122.6 (3)
N3—C4—C3	120.7 (3)	C16—C17—C20	120.3 (3)
C5—C4—C3	116.5 (3)	C19—C18—C17	121.6 (3)
C6—C5—C4	121.4 (3)	C19—C18—H18	119.2
C6—C5—H5	119.3	C17—C18—H18	119.2
C4—C5—H5	119.3	C18—C19—C14	121.8 (3)
C7—C6—C5	121.9 (3)	C18—C19—H19	119.1
C7—C6—H6A	119.0	C14—C19—H19	119.1
C5—C6—H6A	119.1	N5—C20—C17	123.1 (3)
C6—C7—C8	117.2 (3)	N5—C20—H20	118.4
C6—C7—C9	119.6 (3)	C17—C20—H20	118.4
C8—C7—C9	123.3 (3)	O2—C21—N6	119.5 (3)
C3—C8—C7	121.4 (3)	O2—C21—C22	122.0 (3)
C3—C8—H8	119.3	N6—C21—C22	118.5 (3)
C7—C8—H8	119.3	C21—C22—H22A	109.5
N1—C9—C7	123.0 (3)	C21—C22—H22B	109.5
N1—C9—H9	118.5	H22A—C22—H22B	109.5
C7—C9—H9	118.5	C21—C22—H22C	109.5
O1—C10—N2	120.0 (3)	H22A—C22—H22C	109.5
O1—C10—C11	121.5 (3)	H22B—C22—H22C	109.5
N2—C10—C11	118.5 (3)	C9—N1—N2	115.3 (3)
C10—C11—H11A	109.5	C10—N2—N1	122.1 (3)
C10—C11—H11B	109.4	C10—N2—H2	119.0
H11A—C11—H11B	109.5	N1—N2—H2	119.0
C10—C11—H11C	109.5	C4—N3—C2	119.7 (3)
H11A—C11—H11C	109.5	C4—N3—C1	121.0 (3)
H11B—C11—H11C	109.5	C2—N3—C1	117.2 (3)
N4—C12—H12A	109.5	C14—N4—C13	120.0 (3)
N4—C12—H12B	109.5	C14—N4—C12	120.2 (3)
H12A—C12—H12B	109.5	C13—N4—C12	116.9 (3)
N4—C12—H12C	109.5	C20—N5—N6	114.9 (3)
H12A—C12—H12C	109.5	C21—N6—N5	123.0 (3)
H12B—C12—H12C	109.5	C21—N6—H6	118.5
N4—C13—H13A	109.5	N5—N6—H6	118.5
C8—C3—C4—N3	179.7 (3)	N4—C14—C19—C18	−177.7 (3)
C8—C3—C4—C5	0.5 (5)	C15—C14—C19—C18	2.7 (5)
N3—C4—C5—C6	180.0 (3)	C18—C17—C20—N5	−4.0 (5)
C3—C4—C5—C6	−0.8 (5)	C16—C17—C20—N5	174.0 (3)
C4—C5—C6—C7	−0.3 (5)	C7—C9—N1—N2	179.6 (3)
C5—C6—C7—C8	1.6 (5)	O1—C10—N2—N1	175.8 (3)
C5—C6—C7—C9	−178.4 (3)	C11—C10—N2—N1	−4.8 (5)
C4—C3—C8—C7	0.9 (5)	C9—N1—N2—C10	−176.2 (3)
C6—C7—C8—C3	−1.9 (5)	C5—C4—N3—C2	2.0 (5)
C9—C7—C8—C3	178.1 (3)	C3—C4—N3—C2	−177.1 (3)
C6—C7—C9—N1	176.0 (3)	C5—C4—N3—C1	−160.9 (3)
C8—C7—C9—N1	−4.0 (5)	C3—C4—N3—C1	20.0 (5)
N4—C14—C15—C16	178.1 (3)	C19—C14—N4—C13	13.6 (5)
C19—C14—C15—C16	−2.3 (5)	C15—C14—N4—C13	−166.8 (4)
C14—C15—C16—C17	0.4 (5)	C19—C14—N4—C12	173.7 (3)
C15—C16—C17—C18	1.1 (5)	C15—C14—N4—C12	−6.6 (5)
C15—C16—C17—C20	−177.0 (3)	C17—C20—N5—N6	178.8 (3)
C16—C17—C18—C19	−0.7 (5)	O2—C21—N6—N5	179.0 (3)
C20—C17—C18—C19	177.4 (3)	C22—C21—N6—N5	−1.7 (5)
C17—C18—C19—C14	−1.3 (5)	C20—N5—N6—C21	−179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.86	2.09	2.930 (4)	166
N6—H6···O1ii	0.86	2.04	2.884 (4)	165
C3—H3···O1iii	0.93	2.56	3.328 (4)	140
C11—H11A···N1	0.96	2.31	2.791 (5)	110

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.86	2.09	2.930 (4)	166
N6—H6⋯O1ii	0.86	2.04	2.884 (4)	165
C3—H3⋯O1iii	0.93	2.56	3.328 (4)	140

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