2-(4-Isobutyl-phen-yl)-N'-[1-(4-nitro-phen-yl)ethyl-idene]propanohydrazide.

The mol-ecule of the title compound, C(21)H(25)N(3)O(3), exists in a trans configuration with respect to the ethyl-idene unit. The dihedral angle between the two substituted benzene rings is 86.99 (7)°. The nitro group is twisted from the attached benzene ring at an angle of 17.02 (7)°. In the crystal structure, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds in a face-to-face manner into centrosymmetric dimers. These dimer units are further linked into chains along the c axis by weak C-H⋯O inter-actions. These chains are stacked along the b axis. The crystal is further stabilized by weak C-H⋯π inter-actions.

Related literature

For reference structural data, see: Allen et al. (1987 ▶). For related structures, see, for example: Fun et al. (2008 ▶). For background to the activities and applications of hydrazones, see, for example: Amir & Kumar (2007 ▶); Bedia et al. (2006 ▶); Pasha & Nanjundaswamy (2004 ▶); Rollas et al. (2002 ▶); Sridhar & Perumal (2003 ▶); Terzioglu & Gürsoy (2003 ▶).

Experimental

Crystal data

C21H25N3O3

M = 367.44

Monoclinic,

a = 13.7343 (2) Å

b = 7.9039 (2) Å

c = 20.8408 (3) Å

β = 122.677 (1)°

V = 1904.29 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100.0 (1) K

0.58 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.952, T max = 0.991

24946 measured reflections

5506 independent reflections

4402 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.122

S = 1.05

5506 reflections

248 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003420/is2386sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003420/is2386Isup2.hkl

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

C21H25N3O3	F(000) = 784
Mr = 367.44	Dx = 1.282 Mg m−3
Monoclinic, P21/c	Melting point: 443 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.7343 (2) Å	Cell parameters from 5560 reflections
b = 7.9039 (2) Å	θ = 2.0–30.0°
c = 20.8408 (3) Å	µ = 0.09 mm−1
β = 122.677 (1)°	T = 100 K
V = 1904.29 (7) Å3	Block, colorless
Z = 4	0.58 × 0.20 × 0.10 mm

Bruker SMART APEX2 CCD area-detector diffractometer	5506 independent reflections
Radiation source: fine-focus sealed tube	4402 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 8.33 pixels mm-1	θmax = 30.0°, θmin = 2.0°
ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→11
Tmin = 0.952, Tmax = 0.991	l = −29→29
24946 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0567P)2 + 0.5875P] where P = (Fo2 + 2Fc2)/3
5506 reflections	(Δ/σ)max = 0.001
248 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O1	0.61564 (7)	1.53156 (12)	0.98872 (5)	0.02087 (19)
O2	0.39321 (8)	0.36757 (13)	0.73982 (5)	0.0250 (2)
O3	0.25151 (8)	0.31704 (13)	0.75538 (6)	0.0285 (2)
N1	0.50374 (8)	1.30105 (14)	0.94275 (6)	0.0169 (2)
H1	0.4687	1.3350	0.9661	0.020*
N2	0.47995 (8)	1.14801 (14)	0.90567 (5)	0.0162 (2)
N3	0.32794 (9)	0.40891 (14)	0.76090 (6)	0.0200 (2)
C1	0.74608 (10)	1.05444 (16)	0.93547 (7)	0.0173 (2)
H1A	0.6838	1.0228	0.8877	0.021*
C2	0.83450 (10)	0.93944 (16)	0.97821 (7)	0.0184 (2)
H2A	0.8310	0.8328	0.9582	0.022*
C3	0.92861 (10)	0.98084 (16)	1.05069 (7)	0.0176 (2)
C4	0.93176 (10)	1.14328 (17)	1.07810 (7)	0.0195 (2)
H4A	0.9937	1.1745	1.1260	0.023*
C5	0.84359 (10)	1.25954 (17)	1.03485 (7)	0.0180 (2)
H5A	0.8479	1.3672	1.0542	0.022*
C6	0.74891 (10)	1.21660 (16)	0.96282 (6)	0.0158 (2)
C7	0.65444 (10)	1.34418 (16)	0.91325 (7)	0.0168 (2)
H7A	0.5983	1.2892	0.8649	0.020*
C8	0.59144 (10)	1.40054 (16)	0.95135 (6)	0.0162 (2)
C9	0.39775 (9)	1.05845 (16)	0.90156 (6)	0.0159 (2)
C10	0.37649 (10)	0.89227 (16)	0.86281 (6)	0.0158 (2)
C11	0.42259 (10)	0.85604 (17)	0.81818 (7)	0.0188 (2)
H11A	0.4638	0.9391	0.8110	0.023*
C12	0.40751 (10)	0.69891 (17)	0.78498 (7)	0.0193 (2)
H12A	0.4395	0.6750	0.7564	0.023*
C13	0.34376 (10)	0.57704 (16)	0.79498 (6)	0.0173 (2)
C14	0.29521 (10)	0.60950 (17)	0.83742 (7)	0.0187 (2)
H14A	0.2521	0.5272	0.8431	0.022*
C15	0.31236 (10)	0.76689 (17)	0.87100 (7)	0.0185 (2)
H15A	0.2804	0.7897	0.8997	0.022*
C16	1.02083 (10)	0.85055 (17)	1.09705 (7)	0.0202 (2)
H16A	1.0898	0.9078	1.1368	0.024*
H16B	1.0405	0.7935	1.0643	0.024*
C17	0.98418 (10)	0.71672 (17)	1.13418 (7)	0.0184 (2)
H17A	0.9073	0.6748	1.0951	0.022*
C18	1.06782 (11)	0.56769 (18)	1.16314 (8)	0.0241 (3)
H18A	1.0453	0.4871	1.1873	0.036*
H18B	1.1447	0.6073	1.1993	0.036*
H18C	1.0661	0.5148	1.1211	0.036*
C19	0.97652 (11)	0.7941 (2)	1.19870 (7)	0.0249 (3)
H19A	0.9454	0.7121	1.2169	0.037*
H19B	0.9270	0.8916	1.1800	0.037*
H19C	1.0524	0.8271	1.2397	0.037*
C20	0.70381 (11)	1.49872 (18)	0.89582 (8)	0.0226 (3)
H20A	0.7384	1.4634	0.8685	0.034*
H20B	0.7613	1.5519	0.9427	0.034*
H20C	0.6427	1.5776	0.8654	0.034*
C21	0.32900 (10)	1.11330 (18)	0.93465 (7)	0.0203 (3)
H21A	0.2933	1.2206	0.9134	0.030*
H21B	0.3794	1.1236	0.9890	0.030*
H21C	0.2703	1.0307	0.9227	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0209 (4)	0.0185 (5)	0.0261 (4)	−0.0017 (4)	0.0145 (4)	−0.0043 (4)
O2	0.0296 (5)	0.0246 (5)	0.0256 (4)	0.0039 (4)	0.0180 (4)	−0.0002 (4)
O3	0.0281 (5)	0.0212 (5)	0.0368 (5)	−0.0066 (4)	0.0178 (4)	−0.0043 (4)
N1	0.0166 (4)	0.0165 (5)	0.0205 (5)	0.0000 (4)	0.0119 (4)	−0.0017 (4)
N2	0.0159 (4)	0.0148 (5)	0.0172 (4)	0.0005 (4)	0.0085 (4)	0.0000 (4)
N3	0.0211 (5)	0.0181 (5)	0.0180 (5)	0.0016 (4)	0.0088 (4)	0.0020 (4)
C1	0.0178 (5)	0.0173 (6)	0.0187 (5)	−0.0028 (5)	0.0110 (4)	−0.0025 (5)
C2	0.0221 (6)	0.0140 (6)	0.0243 (6)	−0.0011 (5)	0.0159 (5)	−0.0013 (5)
C3	0.0171 (5)	0.0164 (6)	0.0240 (5)	−0.0009 (5)	0.0142 (5)	0.0017 (5)
C4	0.0164 (5)	0.0205 (7)	0.0209 (5)	−0.0024 (5)	0.0097 (5)	−0.0013 (5)
C5	0.0183 (5)	0.0157 (6)	0.0216 (5)	−0.0011 (5)	0.0117 (5)	−0.0023 (5)
C6	0.0152 (5)	0.0164 (6)	0.0196 (5)	−0.0007 (5)	0.0119 (4)	0.0003 (5)
C7	0.0165 (5)	0.0179 (6)	0.0182 (5)	0.0005 (5)	0.0109 (4)	0.0002 (5)
C8	0.0144 (5)	0.0172 (6)	0.0161 (5)	0.0022 (5)	0.0076 (4)	0.0021 (5)
C9	0.0132 (5)	0.0187 (6)	0.0151 (5)	0.0025 (5)	0.0071 (4)	0.0022 (4)
C10	0.0132 (5)	0.0177 (6)	0.0150 (5)	0.0016 (5)	0.0066 (4)	0.0018 (4)
C11	0.0185 (5)	0.0210 (6)	0.0197 (5)	−0.0026 (5)	0.0122 (5)	0.0003 (5)
C12	0.0194 (5)	0.0223 (6)	0.0180 (5)	−0.0009 (5)	0.0112 (5)	−0.0008 (5)
C13	0.0159 (5)	0.0172 (6)	0.0158 (5)	0.0011 (5)	0.0066 (4)	0.0001 (5)
C14	0.0168 (5)	0.0189 (6)	0.0208 (5)	−0.0004 (5)	0.0104 (5)	0.0029 (5)
C15	0.0165 (5)	0.0216 (6)	0.0192 (5)	0.0010 (5)	0.0109 (4)	0.0013 (5)
C16	0.0174 (5)	0.0192 (6)	0.0269 (6)	0.0016 (5)	0.0140 (5)	0.0027 (5)
C17	0.0163 (5)	0.0188 (6)	0.0202 (5)	−0.0007 (5)	0.0100 (4)	0.0007 (5)
C18	0.0240 (6)	0.0213 (7)	0.0270 (6)	0.0026 (6)	0.0136 (5)	0.0043 (5)
C19	0.0217 (6)	0.0319 (8)	0.0221 (6)	0.0016 (6)	0.0125 (5)	0.0005 (6)
C20	0.0229 (6)	0.0221 (7)	0.0271 (6)	0.0002 (5)	0.0162 (5)	0.0036 (5)
C21	0.0183 (5)	0.0209 (6)	0.0263 (6)	−0.0006 (5)	0.0150 (5)	−0.0014 (5)

O1—C8	1.2288 (15)	C11—C12	1.3819 (18)
O2—N3	1.2364 (13)	C11—H11A	0.9300
O3—N3	1.2297 (14)	C12—C13	1.3910 (17)
N1—C8	1.3668 (15)	C12—H12A	0.9300
N1—N2	1.3764 (15)	C13—C14	1.3892 (16)
N1—H1	0.8906	C14—C15	1.3837 (18)
N2—C9	1.2956 (15)	C14—H14A	0.9300
N3—C13	1.4667 (17)	C15—H15A	0.9300
C1—C2	1.3879 (18)	C16—C17	1.5465 (17)
C1—C6	1.3947 (17)	C16—H16A	0.9700
C1—H1A	0.9300	C16—H16B	0.9700
C2—C3	1.3969 (17)	C17—C18	1.5241 (18)
C2—H2A	0.9300	C17—C19	1.5315 (17)
C3—C4	1.3964 (18)	C17—H17A	0.9800
C3—C16	1.5089 (17)	C18—H18A	0.9600
C4—C5	1.3945 (18)	C18—H18B	0.9600
C4—H4A	0.9300	C18—H18C	0.9600
C5—C6	1.3971 (17)	C19—H19A	0.9600
C5—H5A	0.9300	C19—H19B	0.9600
C6—C7	1.5232 (17)	C19—H19C	0.9600
C7—C8	1.5231 (15)	C20—H20A	0.9600
C7—C20	1.5328 (18)	C20—H20B	0.9600
C7—H7A	0.9800	C20—H20C	0.9600
C9—C10	1.4860 (18)	C21—H21A	0.9600
C9—C21	1.5027 (15)	C21—H21B	0.9600
C10—C15	1.3962 (17)	C21—H21C	0.9600
C10—C11	1.4083 (15)
C8—N1—N2	120.30 (9)	C14—C13—C12	121.66 (12)
C8—N1—H1	116.9	C14—C13—N3	118.64 (11)
N2—N1—H1	122.5	C12—C13—N3	119.70 (10)
C9—N2—N1	116.84 (10)	C15—C14—C13	118.61 (11)
O3—N3—O2	123.84 (12)	C15—C14—H14A	120.7
O3—N3—C13	118.43 (10)	C13—C14—H14A	120.7
O2—N3—C13	117.73 (10)	C14—C15—C10	121.51 (10)
C2—C1—C6	121.19 (11)	C14—C15—H15A	119.2
C2—C1—H1A	119.4	C10—C15—H15A	119.2
C6—C1—H1A	119.4	C3—C16—C17	113.56 (10)
C1—C2—C3	121.25 (12)	C3—C16—H16A	108.9
C1—C2—H2A	119.4	C17—C16—H16A	108.9
C3—C2—H2A	119.4	C3—C16—H16B	108.9
C4—C3—C2	117.64 (11)	C17—C16—H16B	108.9
C4—C3—C16	122.38 (11)	H16A—C16—H16B	107.7
C2—C3—C16	119.96 (12)	C18—C17—C19	110.81 (10)
C5—C4—C3	121.14 (11)	C18—C17—C16	110.33 (10)
C5—C4—H4A	119.4	C19—C17—C16	111.19 (11)
C3—C4—H4A	119.4	C18—C17—H17A	108.1
C4—C5—C6	120.94 (12)	C19—C17—H17A	108.1
C4—C5—H5A	119.5	C16—C17—H17A	108.1
C6—C5—H5A	119.5	C17—C18—H18A	109.5
C1—C6—C5	117.83 (11)	C17—C18—H18B	109.5
C1—C6—C7	120.37 (11)	H18A—C18—H18B	109.5
C5—C6—C7	121.72 (11)	C17—C18—H18C	109.5
C8—C7—C6	110.83 (9)	H18A—C18—H18C	109.5
C8—C7—C20	109.81 (11)	H18B—C18—H18C	109.5
C6—C7—C20	111.38 (10)	C17—C19—H19A	109.5
C8—C7—H7A	108.2	C17—C19—H19B	109.5
C6—C7—H7A	108.2	H19A—C19—H19B	109.5
C20—C7—H7A	108.2	C17—C19—H19C	109.5
O1—C8—N1	119.05 (10)	H19A—C19—H19C	109.5
O1—C8—C7	122.79 (11)	H19B—C19—H19C	109.5
N1—C8—C7	118.16 (11)	C7—C20—H20A	109.5
N2—C9—C10	115.30 (10)	C7—C20—H20B	109.5
N2—C9—C21	123.58 (12)	H20A—C20—H20B	109.5
C10—C9—C21	121.11 (10)	C7—C20—H20C	109.5
C15—C10—C11	118.33 (11)	H20A—C20—H20C	109.5
C15—C10—C9	120.84 (10)	H20B—C20—H20C	109.5
C11—C10—C9	120.81 (11)	C9—C21—H21A	109.5
C12—C11—C10	120.94 (11)	C9—C21—H21B	109.5
C12—C11—H11A	119.5	H21A—C21—H21B	109.5
C10—C11—H11A	119.5	C9—C21—H21C	109.5
C11—C12—C13	118.92 (10)	H21A—C21—H21C	109.5
C11—C12—H12A	120.5	H21B—C21—H21C	109.5
C13—C12—H12A	120.5
C8—N1—N2—C9	178.11 (10)	N2—C9—C10—C15	163.79 (11)
C6—C1—C2—C3	1.07 (17)	C21—C9—C10—C15	−14.89 (17)
C1—C2—C3—C4	−1.20 (17)	N2—C9—C10—C11	−14.87 (16)
C1—C2—C3—C16	177.46 (10)	C21—C9—C10—C11	166.45 (11)
C2—C3—C4—C5	0.48 (17)	C15—C10—C11—C12	−1.73 (17)
C16—C3—C4—C5	−178.13 (10)	C9—C10—C11—C12	176.97 (11)
C3—C4—C5—C6	0.37 (17)	C10—C11—C12—C13	1.28 (18)
C2—C1—C6—C5	−0.19 (16)	C11—C12—C13—C14	−0.03 (18)
C2—C1—C6—C7	176.58 (10)	C11—C12—C13—N3	−179.31 (11)
C4—C5—C6—C1	−0.52 (16)	O3—N3—C13—C14	16.88 (16)
C4—C5—C6—C7	−177.24 (10)	O2—N3—C13—C14	−162.63 (11)
C1—C6—C7—C8	120.04 (12)	O3—N3—C13—C12	−163.82 (11)
C5—C6—C7—C8	−63.31 (14)	O2—N3—C13—C12	16.67 (16)
C1—C6—C7—C20	−117.38 (12)	C12—C13—C14—C15	−0.72 (18)
C5—C6—C7—C20	59.26 (14)	N3—C13—C14—C15	178.56 (10)
N2—N1—C8—O1	−175.54 (10)	C13—C14—C15—C10	0.24 (18)
N2—N1—C8—C7	5.01 (16)	C11—C10—C15—C14	0.95 (17)
C6—C7—C8—O1	96.99 (14)	C9—C10—C15—C14	−177.74 (11)
C20—C7—C8—O1	−26.50 (16)	C4—C3—C16—C17	101.68 (13)
C6—C7—C8—N1	−83.58 (13)	C2—C3—C16—C17	−76.91 (14)
C20—C7—C8—N1	152.94 (11)	C3—C16—C17—C18	166.22 (11)
N1—N2—C9—C10	−178.57 (9)	C3—C16—C17—C19	−70.42 (14)
N1—N2—C9—C21	0.07 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.89	2.13	3.0012 (16)	167
C1—H1A···O2ii	0.93	2.58	3.4118 (15)	149
C16—H16B···Cg1iii	0.97	2.88	3.6113 (16)	133
C18—H18B···Cg2iv	0.96	2.99	3.9348 (16)	167
C21—H21C···Cg1v	0.96	2.80	3.5600 (16)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.89	2.13	3.0012 (16)	167
C1—H1A⋯O2ii	0.93	2.58	3.4118 (15)	149
C16—H16B⋯Cg1iii	0.97	2.88	3.6113 (16)	133
C18—H18B⋯Cg2iv	0.96	2.99	3.9348 (16)	167
C21—H21C⋯Cg1v	0.96	2.80	3.5600 (16)	137

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