4-But-oxy-N'-[1-(4-methyl-phen-yl)ethyl-idene]benzohydrazide.

The mol-ecule of the title compound, C(20)H(24)N(2)O(2), exists in a trans conformation with respect to the C=N bond. The dihedral angle between the benzene rings is 79.0 (1)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [001]. Two weak C-H⋯O inter-actions also occur.

Related literature

For acyl­hydrazone compounds, see: Rollas & Küçükgüzel (2007 ▶); Vicini et al. (2006 ▶); Chimenti et al. (2007 ▶). For aroylhydrazone compounds, see: Barbazan et al., 2008 ▶; Dang et al., 2007 ▶. Hydrazones typically act as bi- and tridentate, mono or biprotic depending on the reaction conditions, see: Gup & Kirkan (2005 ▶); Naskar et al. (2004 ▶); Sreeja et al. (2003 ▶). For bond lengths and angles in similar structures, see: Li & Ban (2009 ▶); Mao et al. (2011 ▶); Singh & Singh (2010 ▶).

Experimental

Crystal data

C20H24N2O2

M = 324.41

Monoclinic,

a = 15.0800 (4) Å

b = 14.0134 (4) Å

c = 8.2419 (2) Å

β = 94.609 (2)°

V = 1736.06 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 105 K

0.38 × 0.21 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.970, T max = 0.987

8163 measured reflections

2150 independent reflections

1980 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 0.93

2150 reflections

220 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536812035921/bq2373sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035921/bq2373Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035921/bq2373Isup3.cml

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

C20H24N2O2	F(000) = 696
Mr = 324.41	Dx = 1.241 Mg m−3
Monoclinic, C1c1	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C-2yc	Cell parameters from 3295 reflections
a = 15.0800 (4) Å	θ = 2.7–28.2°
b = 14.0134 (4) Å	µ = 0.08 mm−1
c = 8.2419 (2) Å	T = 105 K
β = 94.609 (2)°	Prism, colourless
V = 1736.06 (8) Å3	0.38 × 0.21 × 0.17 mm
Z = 4

Bruker APEXII CCD diffractometer	2150 independent reflections
Radiation source: sealed tube	1980 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan (Blessing, 1995)	h = −20→14
Tmin = 0.970, Tmax = 0.987	k = −18→17
8163 measured reflections	l = −10→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.7866P] where P = (Fo2 + 2Fc2)/3
2150 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.38 e Å−3
2 restraints	Δρmin = −0.20 e Å−3

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	0.37326 (10)	0.84731 (12)	0.17841 (19)	0.0229 (4)
O2	0.09570 (11)	0.91173 (11)	0.70734 (19)	0.0221 (3)
N1	0.02616 (12)	0.99195 (14)	0.4926 (2)	0.0206 (4)
H1	0.0300	1.0165	0.3952	0.025*
N2	−0.04815 (12)	1.00759 (14)	0.5785 (2)	0.0204 (4)
C1	0.47160 (18)	0.8908 (2)	−0.2273 (3)	0.0316 (6)
H1A	0.4698	0.8420	−0.3127	0.047*
H1B	0.5106	0.9431	−0.2557	0.047*
H1C	0.4114	0.9154	−0.2174	0.047*
C2	0.50729 (16)	0.84699 (19)	−0.0661 (3)	0.0265 (5)
H2A	0.5691	0.8250	−0.0755	0.032*
H2B	0.5089	0.8966	0.0195	0.032*
C3	0.45168 (16)	0.76347 (18)	−0.0149 (3)	0.0261 (5)
H3A	0.4450	0.7172	−0.1059	0.031*
H3B	0.4843	0.7310	0.0785	0.031*
C4	0.36010 (16)	0.79010 (17)	0.0327 (3)	0.0236 (5)
H4A	0.3274	0.8269	−0.0555	0.028*
H4B	0.3255	0.7320	0.0540	0.028*
C5	0.30078 (15)	0.86690 (15)	0.2613 (3)	0.0186 (4)
C6	0.31990 (15)	0.90727 (16)	0.4156 (3)	0.0198 (4)
H6	0.3799	0.9204	0.4533	0.024*
C7	0.25217 (14)	0.92824 (15)	0.5135 (3)	0.0192 (4)
H7	0.2658	0.9530	0.6199	0.023*
C8	0.16373 (14)	0.91299 (15)	0.4559 (3)	0.0181 (4)
C9	0.09251 (14)	0.93751 (15)	0.5645 (3)	0.0191 (4)
C10	−0.09609 (14)	1.08078 (16)	0.5367 (3)	0.0190 (4)
C11	−0.17777 (14)	1.09221 (16)	0.6243 (3)	0.0179 (4)
C12	−0.21596 (15)	1.01299 (16)	0.6959 (3)	0.0217 (5)
H12	−0.1916	0.9512	0.6826	0.026*
C13	−0.28925 (15)	1.02417 (17)	0.7862 (3)	0.0230 (5)
H13	−0.3136	0.9700	0.8358	0.028*
C14	−0.32750 (15)	1.11314 (17)	0.8052 (3)	0.0218 (5)
C15	−0.40582 (17)	1.1251 (2)	0.9068 (3)	0.0296 (5)
H15A	−0.4605	1.1320	0.8350	0.044*
H15B	−0.3971	1.1822	0.9749	0.044*
H15C	−0.4107	1.0690	0.9764	0.044*
C16	−0.07349 (17)	1.15369 (17)	0.4137 (3)	0.0257 (5)
H16A	−0.0238	1.1930	0.4591	0.039*
H16B	−0.1254	1.1944	0.3861	0.039*
H16C	−0.0565	1.1214	0.3154	0.039*
C17	−0.29159 (15)	1.19105 (16)	0.7300 (3)	0.0224 (5)
H17	−0.3177	1.2523	0.7398	0.027*
C18	−0.21795 (15)	1.18082 (16)	0.6403 (3)	0.0212 (5)
H18	−0.1947	1.2351	0.5893	0.025*
C19	0.14483 (15)	0.87441 (15)	0.3012 (3)	0.0211 (4)
H19	0.0847	0.8651	0.2608	0.025*
C20	0.21321 (15)	0.84930 (16)	0.2050 (3)	0.0210 (5)
H20	0.1999	0.8204	0.1017	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0193 (8)	0.0298 (8)	0.0200 (8)	0.0002 (7)	0.0046 (6)	−0.0030 (7)
O2	0.0206 (8)	0.0230 (8)	0.0234 (8)	0.0035 (6)	0.0065 (6)	0.0007 (7)
N1	0.0184 (9)	0.0230 (10)	0.0213 (9)	0.0036 (7)	0.0079 (7)	0.0040 (7)
N2	0.0155 (9)	0.0244 (9)	0.0221 (9)	0.0012 (7)	0.0073 (7)	0.0001 (8)
C1	0.0303 (14)	0.0420 (14)	0.0229 (12)	−0.0006 (11)	0.0049 (10)	0.0029 (11)
C2	0.0195 (11)	0.0408 (14)	0.0199 (11)	0.0031 (9)	0.0054 (9)	−0.0002 (10)
C3	0.0264 (12)	0.0311 (12)	0.0214 (10)	0.0085 (9)	0.0061 (9)	−0.0001 (10)
C4	0.0249 (11)	0.0263 (11)	0.0202 (10)	0.0001 (9)	0.0063 (8)	−0.0031 (9)
C5	0.0186 (10)	0.0174 (10)	0.0202 (10)	0.0021 (8)	0.0046 (8)	0.0019 (8)
C6	0.0170 (10)	0.0211 (11)	0.0210 (11)	0.0005 (8)	−0.0011 (8)	0.0020 (8)
C7	0.0200 (11)	0.0159 (10)	0.0215 (11)	0.0030 (8)	0.0012 (9)	−0.0002 (8)
C8	0.0173 (11)	0.0150 (9)	0.0228 (11)	0.0021 (7)	0.0061 (8)	0.0030 (8)
C9	0.0169 (10)	0.0164 (10)	0.0247 (11)	−0.0017 (8)	0.0070 (8)	−0.0005 (8)
C10	0.0187 (10)	0.0179 (10)	0.0209 (10)	−0.0005 (8)	0.0045 (8)	−0.0008 (8)
C11	0.0161 (10)	0.0215 (10)	0.0162 (10)	0.0014 (8)	0.0020 (8)	−0.0004 (9)
C12	0.0207 (11)	0.0180 (11)	0.0263 (11)	0.0029 (8)	0.0021 (8)	0.0023 (9)
C13	0.0186 (10)	0.0249 (11)	0.0259 (11)	0.0003 (9)	0.0033 (9)	0.0044 (9)
C14	0.0171 (10)	0.0317 (12)	0.0167 (10)	0.0012 (9)	0.0025 (8)	−0.0017 (9)
C15	0.0213 (12)	0.0370 (14)	0.0313 (13)	0.0036 (10)	0.0075 (10)	−0.0024 (11)
C16	0.0295 (12)	0.0216 (11)	0.0275 (12)	0.0023 (9)	0.0114 (10)	0.0033 (9)
C17	0.0203 (11)	0.0217 (11)	0.0252 (11)	0.0045 (8)	0.0023 (9)	−0.0032 (9)
C18	0.0232 (11)	0.0188 (10)	0.0218 (11)	0.0006 (8)	0.0031 (9)	0.0014 (9)
C19	0.0152 (10)	0.0211 (10)	0.0270 (11)	−0.0007 (8)	0.0018 (8)	0.0009 (9)
C20	0.0214 (11)	0.0238 (11)	0.0181 (10)	−0.0002 (8)	0.0046 (8)	−0.0009 (9)

O1—C5	1.363 (3)	C8—C19	1.393 (3)
O1—C4	1.444 (3)	C8—C9	1.492 (3)
O2—C9	1.229 (3)	C10—C11	1.485 (3)
N1—C9	1.356 (3)	C10—C16	1.498 (3)
N1—N2	1.390 (2)	C11—C18	1.393 (3)
N1—H1	0.8800	C11—C12	1.403 (3)
N2—C10	1.286 (3)	C12—C13	1.390 (3)
C1—C2	1.522 (3)	C12—H12	0.9500
C1—H1A	0.9800	C13—C14	1.388 (3)
C1—H1B	0.9800	C13—H13	0.9500
C1—H1C	0.9800	C14—C17	1.387 (3)
C2—C3	1.519 (4)	C14—C15	1.511 (3)
C2—H2A	0.9900	C15—H15A	0.9800
C2—H2B	0.9900	C15—H15B	0.9800
C3—C4	1.512 (3)	C15—H15C	0.9800
C3—H3A	0.9900	C16—H16A	0.9800
C3—H3B	0.9900	C16—H16B	0.9800
C4—H4A	0.9900	C16—H16C	0.9800
C4—H4B	0.9900	C17—C18	1.390 (3)
C5—C20	1.386 (3)	C17—H17	0.9500
C5—C6	1.400 (3)	C18—H18	0.9500
C6—C7	1.383 (3)	C19—C20	1.396 (3)
C6—H6	0.9500	C19—H19	0.9500
C7—C8	1.396 (3)	C20—H20	0.9500
C7—H7	0.9500
C5—O1—C4	117.82 (17)	O2—C9—C8	122.15 (19)
C9—N1—N2	117.58 (17)	N1—C9—C8	114.14 (19)
C9—N1—H1	121.2	N2—C10—C11	115.23 (19)
N2—N1—H1	121.2	N2—C10—C16	124.9 (2)
C10—N2—N1	116.62 (18)	C11—C10—C16	119.86 (19)
C2—C1—H1A	109.5	C18—C11—C12	118.0 (2)
C2—C1—H1B	109.5	C18—C11—C10	121.8 (2)
H1A—C1—H1B	109.5	C12—C11—C10	120.24 (19)
C2—C1—H1C	109.5	C13—C12—C11	120.5 (2)
H1A—C1—H1C	109.5	C13—C12—H12	119.8
H1B—C1—H1C	109.5	C11—C12—H12	119.8
C3—C2—C1	112.9 (2)	C14—C13—C12	121.2 (2)
C3—C2—H2A	109.0	C14—C13—H13	119.4
C1—C2—H2A	109.0	C12—C13—H13	119.4
C3—C2—H2B	109.0	C17—C14—C13	118.4 (2)
C1—C2—H2B	109.0	C17—C14—C15	120.7 (2)
H2A—C2—H2B	107.8	C13—C14—C15	120.9 (2)
C4—C3—C2	114.7 (2)	C14—C15—H15A	109.5
C4—C3—H3A	108.6	C14—C15—H15B	109.5
C2—C3—H3A	108.6	H15A—C15—H15B	109.5
C4—C3—H3B	108.6	C14—C15—H15C	109.5
C2—C3—H3B	108.6	H15A—C15—H15C	109.5
H3A—C3—H3B	107.6	H15B—C15—H15C	109.5
O1—C4—C3	106.59 (19)	C10—C16—H16A	109.5
O1—C4—H4A	110.4	C10—C16—H16B	109.5
C3—C4—H4A	110.4	H16A—C16—H16B	109.5
O1—C4—H4B	110.4	C10—C16—H16C	109.5
C3—C4—H4B	110.4	H16A—C16—H16C	109.5
H4A—C4—H4B	108.6	H16B—C16—H16C	109.5
O1—C5—C20	125.24 (19)	C14—C17—C18	120.9 (2)
O1—C5—C6	114.95 (19)	C14—C17—H17	119.5
C20—C5—C6	119.81 (19)	C18—C17—H17	119.5
C7—C6—C5	120.5 (2)	C17—C18—C11	121.0 (2)
C7—C6—H6	119.7	C17—C18—H18	119.5
C5—C6—H6	119.7	C11—C18—H18	119.5
C6—C7—C8	120.0 (2)	C8—C19—C20	120.8 (2)
C6—C7—H7	120.0	C8—C19—H19	119.6
C8—C7—H7	120.0	C20—C19—H19	119.6
C19—C8—C7	119.36 (19)	C5—C20—C19	119.5 (2)
C19—C8—C9	122.27 (19)	C5—C20—H20	120.3
C7—C8—C9	118.4 (2)	C19—C20—H20	120.3
O2—C9—N1	123.69 (19)
C9—N1—N2—C10	158.6 (2)	N2—C10—C11—C18	155.7 (2)
C1—C2—C3—C4	−68.9 (3)	C16—C10—C11—C18	−22.4 (3)
C5—O1—C4—C3	−169.15 (18)	N2—C10—C11—C12	−23.3 (3)
C2—C3—C4—O1	−65.7 (3)	C16—C10—C11—C12	158.6 (2)
C4—O1—C5—C20	−10.6 (3)	C18—C11—C12—C13	−2.9 (3)
C4—O1—C5—C6	168.89 (18)	C10—C11—C12—C13	176.1 (2)
O1—C5—C6—C7	−178.39 (19)	C11—C12—C13—C14	1.3 (4)
C20—C5—C6—C7	1.1 (3)	C12—C13—C14—C17	0.8 (3)
C5—C6—C7—C8	−2.8 (3)	C12—C13—C14—C15	−178.6 (2)
C6—C7—C8—C19	1.6 (3)	C13—C14—C17—C18	−1.3 (3)
C6—C7—C8—C9	−179.34 (19)	C15—C14—C17—C18	178.1 (2)
N2—N1—C9—O2	−9.6 (3)	C14—C17—C18—C11	−0.4 (3)
N2—N1—C9—C8	171.93 (18)	C12—C11—C18—C17	2.4 (3)
C19—C8—C9—O2	130.8 (2)	C10—C11—C18—C17	−176.6 (2)
C7—C8—C9—O2	−48.2 (3)	C7—C8—C19—C20	1.2 (3)
C19—C8—C9—N1	−50.6 (3)	C9—C8—C19—C20	−177.8 (2)
C7—C8—C9—N1	130.3 (2)	O1—C5—C20—C19	−178.9 (2)
N1—N2—C10—C11	176.57 (18)	C6—C5—C20—C19	1.7 (3)
N1—N2—C10—C16	−5.4 (3)	C8—C19—C20—C5	−2.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.88	2.15	2.975 (2)	155
C16—H16C···O2i	0.98	2.57	3.307 (3)	131
C17—H17···O2ii	0.95	2.59	3.527 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.88	2.15	2.975 (2)	155
C16—H16C⋯O2i	0.98	2.57	3.307 (3)	131
C17—H17⋯O2ii	0.95	2.59	3.527 (3)	168

Symmetry codes: (i) ; (ii) .