2-[4-(2-Methyl-prop-yl)phen-yl]-N'-[(E)-1-phenyl-ethyl-idene]propane-hydrazide.

In the title compound, C(21)H(26)N(2)O, the dihedral angle between the two aromatic rings is 85.90 (19)°. The propenone-hydrazide unit forms dihedral angles of 21.62 (8) and 72.83 (9)°, respectively, with the terminal and central aromatic rings. The 2-methyl-propyl group is disordered over two sites, with occupancies of 0.533 (13) and 0.467 (13). In crystal structure, mol-ecules are linked into centrosymmetric dimers by paired N-H⋯O and C-H⋯O hydrogen bonds. In addition, C-H⋯π inter-actions are observed.

Related literature

For the pharmaceutical applications of ibuprofen, see: Palaska et al. (2002 ▶). For the synthesis of hydrazones, see: Rollas & Küçükgüzel (2007 ▶). For the pharmaceutical applications of hydrazones, see: Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Terzioglu & Gürsoy (2003 ▶). For a related structure, see: Fun et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H26N2O

M = 322.44

Triclinic,

a = 5.4355 (2) Å

b = 10.2850 (4) Å

c = 17.3095 (6) Å

α = 80.821 (4)°

β = 84.312 (3)°

γ = 74.719 (3)°

V = 919.85 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 100.0 (1) K

0.22 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.984, T max = 0.989

12794 measured reflections

4238 independent reflections

2556 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.194

S = 1.07

4238 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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/S1600536808036817/ci2710sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036817/ci2710Isup2.hkl

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

C21H26N2O	Z = 2
Mr = 322.44	F000 = 348
Triclinic, P1	Dx = 1.164 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.4355 (2) Å	Cell parameters from 2156 reflections
b = 10.2850 (4) Å	θ = 2.6–26.3º
c = 17.3095 (6) Å	µ = 0.07 mm−1
α = 80.821 (4)º	T = 100.0 (1) K
β = 84.312 (3)º	Block, colourless
γ = 74.719 (3)º	0.22 × 0.20 × 0.15 mm
V = 919.85 (6) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4238 independent reflections
Radiation source: fine-focus sealed tube	2556 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.063
T = 100.0(1) K	θmax = 27.5º
φ and ω scans	θmin = 1.2º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.984, Tmax = 0.989	k = −13→13
12794 measured reflections	l = −22→22

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)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.194	w = 1/[σ2(Fo2) + (0.0958P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
4238 reflections	Δρmax = 0.33 e Å−3
255 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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

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	Occ. (<1)
O1	−0.0323 (4)	1.15692 (18)	0.02969 (11)	0.0501 (6)
N1	0.4274 (4)	0.90562 (19)	0.13372 (11)	0.0262 (5)
N2	0.2392 (4)	0.9662 (2)	0.08205 (12)	0.0313 (5)
C1	0.8421 (4)	0.8048 (2)	0.22728 (13)	0.0279 (5)
H1A	0.7995	0.8977	0.2095	0.033*
C2	1.0316 (5)	0.7513 (3)	0.27947 (14)	0.0310 (6)
H2A	1.1146	0.8087	0.2967	0.037*
C3	1.0993 (5)	0.6133 (3)	0.30636 (14)	0.0315 (6)
H3A	1.2282	0.5778	0.3411	0.038*
C4	0.9730 (5)	0.5284 (3)	0.28104 (14)	0.0313 (6)
H4A	1.0165	0.4356	0.2990	0.038*
C5	0.7821 (4)	0.5819 (2)	0.22888 (14)	0.0274 (5)
H5A	0.6985	0.5241	0.2123	0.033*
C6	0.7130 (4)	0.7198 (2)	0.20080 (13)	0.0244 (5)
C7	0.5099 (4)	0.7754 (2)	0.14382 (13)	0.0250 (5)
C8	0.1345 (5)	1.1015 (2)	0.07640 (14)	0.0342 (6)
C9	0.2172 (5)	1.1812 (2)	0.13175 (13)	0.0285 (6)
H9A	0.3966	1.1389	0.1424	0.034*
C10	0.0556 (4)	1.1707 (2)	0.20861 (13)	0.0236 (5)
C11	−0.2016 (4)	1.2400 (2)	0.21324 (14)	0.0276 (6)
H11A	−0.2775	1.2898	0.1682	0.033*
C12	−0.3465 (5)	1.2360 (2)	0.28371 (15)	0.0314 (6)
H12A	−0.5168	1.2851	0.2854	0.038*
C13	−0.2420 (5)	1.1600 (2)	0.35198 (14)	0.0288 (6)
C14	0.0141 (5)	1.0878 (2)	0.34642 (14)	0.0285 (5)
H14A	0.0887	1.0349	0.3909	0.034*
C15	0.1596 (5)	1.0932 (2)	0.27617 (13)	0.0261 (5)
H15A	0.3298	1.0441	0.2743	0.031*
C16	−0.3971 (5)	1.1569 (3)	0.42892 (15)	0.0398 (7)
H16A	−0.3843	1.0634	0.4501	0.048*	0.467 (13)
H16B	−0.5731	1.1986	0.4190	0.048*	0.467 (13)
H16C	−0.3175	1.0769	0.4631	0.048*	0.533 (13)
H16D	−0.5637	1.1492	0.4198	0.048*	0.533 (13)
C17A	−0.3180 (19)	1.2210 (10)	0.4913 (4)	0.0316 (18)	0.467 (13)
H17A	−0.1511	1.1634	0.5068	0.038*	0.467 (13)
C18A	−0.281 (2)	1.3628 (10)	0.4643 (5)	0.053 (3)	0.467 (13)
H18A	−0.1524	1.3595	0.4218	0.079*	0.467 (13)
H18B	−0.2269	1.3958	0.5070	0.079*	0.467 (13)
H18C	−0.4387	1.4228	0.4470	0.079*	0.467 (13)
C19A	−0.4977 (19)	1.2181 (10)	0.5642 (6)	0.037 (2)	0.467 (13)
H19A	−0.4286	1.2466	0.6057	0.055*	0.467 (13)
H19B	−0.5165	1.1272	0.5801	0.055*	0.467 (13)
H19C	−0.6615	1.2786	0.5530	0.055*	0.467 (13)
C17B	−0.4221 (17)	1.2748 (9)	0.4729 (4)	0.0370 (17)	0.533 (13)
H17B	−0.5134	1.3567	0.4401	0.044*	0.533 (13)
C18B	−0.1698 (15)	1.2984 (10)	0.4884 (4)	0.041 (2)	0.533 (13)
H18D	−0.0717	1.3101	0.4397	0.061*	0.533 (13)
H18E	−0.0771	1.2215	0.5221	0.061*	0.533 (13)
H18F	−0.2002	1.3787	0.5133	0.061*	0.533 (13)
C19B	−0.586 (2)	1.2606 (11)	0.5497 (6)	0.053 (2)	0.533 (13)
H19D	−0.6109	1.3408	0.5743	0.080*	0.533 (13)
H19E	−0.4999	1.1825	0.5841	0.080*	0.533 (13)
H19F	−0.7481	1.2496	0.5388	0.080*	0.533 (13)
C20	0.4176 (5)	0.6775 (2)	0.10498 (14)	0.0311 (6)
H20A	0.3320	0.7251	0.0589	0.047*
H20B	0.3010	0.6385	0.1407	0.047*
H20C	0.5607	0.6065	0.0906	0.047*
C21	0.1932 (6)	1.3288 (2)	0.09447 (15)	0.0388 (7)
H21A	0.2250	1.3800	0.1325	0.058*
H21B	0.0239	1.3677	0.0769	0.058*
H21C	0.3155	1.3314	0.0506	0.058*
H1N2	0.185 (4)	0.923 (2)	0.0516 (14)	0.026 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0774 (15)	0.0287 (10)	0.0408 (11)	0.0079 (10)	−0.0309 (11)	−0.0144 (8)
N1	0.0268 (11)	0.0257 (11)	0.0250 (10)	−0.0033 (8)	−0.0014 (8)	−0.0063 (8)
N2	0.0422 (13)	0.0252 (11)	0.0264 (11)	−0.0018 (9)	−0.0092 (10)	−0.0103 (9)
C1	0.0273 (13)	0.0247 (12)	0.0312 (13)	−0.0046 (10)	0.0033 (11)	−0.0089 (10)
C2	0.0264 (13)	0.0376 (14)	0.0324 (14)	−0.0090 (11)	0.0025 (11)	−0.0160 (11)
C3	0.0247 (13)	0.0370 (15)	0.0321 (14)	−0.0027 (11)	−0.0013 (11)	−0.0114 (11)
C4	0.0317 (14)	0.0266 (13)	0.0330 (14)	−0.0015 (11)	−0.0030 (11)	−0.0051 (10)
C5	0.0282 (13)	0.0236 (12)	0.0320 (13)	−0.0059 (10)	−0.0017 (10)	−0.0094 (10)
C6	0.0226 (12)	0.0265 (12)	0.0239 (12)	−0.0046 (10)	0.0058 (10)	−0.0098 (10)
C7	0.0257 (12)	0.0260 (12)	0.0231 (12)	−0.0047 (10)	0.0036 (10)	−0.0089 (10)
C8	0.0502 (16)	0.0248 (13)	0.0259 (13)	−0.0028 (12)	−0.0074 (12)	−0.0061 (10)
C9	0.0358 (14)	0.0227 (12)	0.0272 (13)	−0.0048 (10)	−0.0030 (11)	−0.0073 (10)
C10	0.0286 (12)	0.0191 (11)	0.0266 (12)	−0.0077 (9)	−0.0053 (10)	−0.0089 (9)
C11	0.0311 (14)	0.0214 (12)	0.0320 (13)	−0.0055 (10)	−0.0123 (11)	−0.0041 (10)
C12	0.0222 (12)	0.0308 (13)	0.0430 (15)	−0.0050 (10)	−0.0033 (11)	−0.0125 (11)
C13	0.0282 (13)	0.0291 (13)	0.0327 (14)	−0.0108 (11)	0.0017 (11)	−0.0109 (11)
C14	0.0326 (14)	0.0255 (13)	0.0263 (13)	−0.0049 (10)	−0.0059 (11)	−0.0019 (10)
C15	0.0272 (13)	0.0222 (12)	0.0291 (13)	−0.0042 (10)	−0.0043 (10)	−0.0064 (10)
C16	0.0325 (15)	0.0487 (17)	0.0395 (16)	−0.0112 (13)	0.0053 (12)	−0.0128 (13)
C17A	0.030 (4)	0.034 (4)	0.028 (3)	−0.004 (3)	−0.006 (3)	0.000 (3)
C18A	0.082 (7)	0.036 (5)	0.039 (4)	−0.009 (5)	−0.003 (4)	−0.012 (4)
C19A	0.031 (5)	0.041 (5)	0.035 (4)	0.001 (4)	−0.002 (4)	−0.013 (4)
C17B	0.030 (4)	0.041 (4)	0.033 (3)	−0.001 (3)	0.001 (3)	−0.002 (3)
C18B	0.039 (4)	0.047 (5)	0.038 (4)	−0.008 (3)	0.005 (3)	−0.016 (3)
C19B	0.041 (5)	0.062 (6)	0.045 (5)	0.006 (4)	0.015 (4)	−0.015 (4)
C20	0.0349 (14)	0.0268 (13)	0.0306 (13)	−0.0009 (11)	−0.0032 (11)	−0.0119 (10)
C21	0.0544 (18)	0.0287 (14)	0.0329 (14)	−0.0108 (13)	0.0035 (13)	−0.0061 (11)

O1—C8	1.236 (3)	C15—H15A	0.9300
N1—C7	1.284 (3)	C16—C17A	1.502 (7)
N1—N2	1.379 (3)	C16—C17B	1.502 (7)
N2—C8	1.349 (3)	C16—H16A	0.9600
N2—H1N2	0.86 (2)	C16—H16B	0.9599
C1—C2	1.381 (3)	C16—H16C	0.9600
C1—C6	1.407 (3)	C16—H16D	0.9600
C1—H1A	0.9300	C17A—C19A	1.519 (13)
C2—C3	1.384 (3)	C17A—C18A	1.519 (14)
C2—H2A	0.9300	C17A—H17A	0.9800
C3—C4	1.387 (3)	C18A—H18A	0.9600
C3—H3A	0.9300	C18A—H18B	0.9600
C4—C5	1.386 (3)	C18A—H18C	0.9600
C4—H4A	0.9300	C19A—H19A	0.9600
C5—C6	1.387 (3)	C19A—H19B	0.9600
C5—H5A	0.9300	C19A—H19C	0.9600
C6—C7	1.491 (3)	C17B—C18B	1.511 (12)
C7—C20	1.506 (3)	C17B—C19B	1.533 (12)
C8—C9	1.524 (3)	C17B—H17B	0.9800
C9—C10	1.525 (3)	C18B—H18D	0.9600
C9—C21	1.529 (3)	C18B—H18E	0.9600
C9—H9A	0.9800	C18B—H18F	0.9600
C10—C15	1.385 (3)	C19B—H19D	0.9600
C10—C11	1.393 (3)	C19B—H19E	0.9600
C11—C12	1.386 (3)	C19B—H19F	0.9600
C11—H11A	0.9300	C20—H20A	0.9600
C12—C13	1.391 (3)	C20—H20B	0.9600
C12—H12A	0.9300	C20—H20C	0.9600
C13—C14	1.396 (3)	C21—H21A	0.9600
C13—C16	1.505 (3)	C21—H21B	0.9600
C14—C15	1.385 (3)	C21—H21C	0.9600
C14—H14A	0.9300
C7—N1—N2	119.18 (19)	C17B—C16—C13	116.1 (3)
C8—N2—N1	119.6 (2)	C17A—C16—H16A	106.5
C8—N2—H1N2	116.6 (16)	C17B—C16—H16A	127.9
N1—N2—H1N2	123.7 (16)	C13—C16—H16A	108.0
C2—C1—C6	120.5 (2)	C17A—C16—H16B	109.7
C2—C1—H1A	119.7	C17B—C16—H16B	84.1
C6—C1—H1A	119.7	C13—C16—H16B	108.4
C1—C2—C3	120.7 (2)	H16A—C16—H16B	107.5
C1—C2—H2A	119.6	C17A—C16—H16C	79.8
C3—C2—H2A	119.6	C17B—C16—H16C	106.1
C2—C3—C4	119.4 (2)	C13—C16—H16C	108.5
C2—C3—H3A	120.3	H16B—C16—H16C	131.7
C4—C3—H3A	120.3	C17A—C16—H16D	129.3
C5—C4—C3	120.0 (2)	C17B—C16—H16D	109.7
C5—C4—H4A	120.0	C13—C16—H16D	108.5
C3—C4—H4A	120.0	H16A—C16—H16D	79.4
C4—C5—C6	121.4 (2)	H16C—C16—H16D	107.7
C4—C5—H5A	119.3	C16—C17A—C19A	111.3 (6)
C6—C5—H5A	119.3	C16—C17A—C18A	114.6 (8)
C5—C6—C1	117.9 (2)	C19A—C17A—C18A	111.4 (7)
C5—C6—C7	120.8 (2)	C16—C17A—H17A	106.3
C1—C6—C7	121.3 (2)	C19A—C17A—H17A	106.3
N1—C7—C6	115.09 (19)	C18A—C17A—H17A	106.3
N1—C7—C20	126.2 (2)	C16—C17B—C18B	114.0 (7)
C6—C7—C20	118.7 (2)	C16—C17B—C19B	111.2 (6)
O1—C8—N2	120.1 (2)	C18B—C17B—C19B	110.3 (7)
O1—C8—C9	121.5 (2)	C16—C17B—H17B	107.0
N2—C8—C9	118.3 (2)	C18B—C17B—H17B	107.0
C8—C9—C10	108.12 (19)	C19B—C17B—H17B	107.0
C8—C9—C21	110.8 (2)	C17B—C18B—H18D	109.5
C10—C9—C21	112.25 (19)	C17B—C18B—H18E	109.5
C8—C9—H9A	108.5	H18D—C18B—H18E	109.5
C10—C9—H9A	108.5	C17B—C18B—H18F	109.5
C21—C9—H9A	108.5	H18D—C18B—H18F	109.5
C15—C10—C11	117.8 (2)	H18E—C18B—H18F	109.5
C15—C10—C9	121.3 (2)	C17B—C19B—H19D	109.5
C11—C10—C9	120.9 (2)	C17B—C19B—H19E	109.5
C12—C11—C10	121.2 (2)	H19D—C19B—H19E	109.5
C12—C11—H11A	119.4	C17B—C19B—H19F	109.5
C10—C11—H11A	119.4	H19D—C19B—H19F	109.5
C11—C12—C13	121.2 (2)	H19E—C19B—H19F	109.5
C11—C12—H12A	119.4	C7—C20—H20A	109.5
C13—C12—H12A	119.4	C7—C20—H20B	109.5
C12—C13—C14	117.3 (2)	H20A—C20—H20B	109.5
C12—C13—C16	121.5 (2)	C7—C20—H20C	109.5
C14—C13—C16	121.3 (2)	H20A—C20—H20C	109.5
C15—C14—C13	121.5 (2)	H20B—C20—H20C	109.5
C15—C14—H14A	119.3	C9—C21—H21A	109.5
C13—C14—H14A	119.3	C9—C21—H21B	109.5
C14—C15—C10	121.0 (2)	H21A—C21—H21B	109.5
C14—C15—H15A	119.5	C9—C21—H21C	109.5
C10—C15—H15A	119.5	H21A—C21—H21C	109.5
C17A—C16—C13	116.4 (3)	H21B—C21—H21C	109.5
C7—N1—N2—C8	173.9 (2)	C21—C9—C10—C11	50.4 (3)
C6—C1—C2—C3	0.4 (3)	C15—C10—C11—C12	2.5 (3)
C1—C2—C3—C4	−0.6 (4)	C9—C10—C11—C12	−176.96 (19)
C2—C3—C4—C5	0.4 (4)	C10—C11—C12—C13	−1.6 (3)
C3—C4—C5—C6	0.1 (4)	C11—C12—C13—C14	−0.2 (3)
C4—C5—C6—C1	−0.4 (3)	C11—C12—C13—C16	179.1 (2)
C4—C5—C6—C7	179.1 (2)	C12—C13—C14—C15	1.0 (3)
C2—C1—C6—C5	0.1 (3)	C16—C13—C14—C15	−178.3 (2)
C2—C1—C6—C7	−179.3 (2)	C13—C14—C15—C10	−0.1 (3)
N2—N1—C7—C6	−179.98 (19)	C11—C10—C15—C14	−1.7 (3)
N2—N1—C7—C20	−1.1 (4)	C9—C10—C15—C14	177.78 (19)
C5—C6—C7—N1	167.0 (2)	C12—C13—C16—C17A	−113.3 (6)
C1—C6—C7—N1	−13.6 (3)	C14—C13—C16—C17A	66.0 (6)
C5—C6—C7—C20	−12.0 (3)	C12—C13—C16—C17B	−81.6 (6)
C1—C6—C7—C20	167.4 (2)	C14—C13—C16—C17B	97.7 (5)
N1—N2—C8—O1	179.2 (2)	C17B—C16—C17A—C19A	80.4 (10)
N1—N2—C8—C9	−3.9 (4)	C13—C16—C17A—C19A	176.9 (5)
O1—C8—C9—C10	92.1 (3)	C17B—C16—C17A—C18A	−47.1 (11)
N2—C8—C9—C10	−84.7 (3)	C13—C16—C17A—C18A	49.4 (12)
O1—C8—C9—C21	−31.3 (4)	C17A—C16—C17B—C18B	42.9 (10)
N2—C8—C9—C21	151.9 (2)	C13—C16—C17B—C18B	−55.0 (10)
C8—C9—C10—C15	108.5 (2)	C17A—C16—C17B—C19B	−82.6 (10)
C21—C9—C10—C15	−129.0 (2)	C13—C16—C17B—C19B	179.6 (4)
C8—C9—C10—C11	−72.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1i	0.86 (2)	2.08 (2)	2.928 (3)	173 (2)
C20—H20A···O1i	0.96	2.31	3.247 (3)	165
C20—H20B···Cg1ii	0.96	2.75	3.609 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.86 (2)	2.08 (2)	2.928 (3)	173 (2)
C20—H20A⋯O1i	0.96	2.31	3.247 (3)	165
C20—H20B⋯Cg1ii	0.96	2.75	3.609 (3)	150

Symmetry codes: (i) ; (ii) .