1-[(Z)-2-Phenyl-hydrazin-1-yl-idene]-1-(piperidin-1-yl)propan-2-one.

A Z configuration about the imine bond [1.3025 (18) Å] in the title compound, C(14)H(19)N(3)O, allows for the formation of an intra-moleclar N-H⋯N hydrogen bond between the hydrazone H and piperidine N atoms; the carbonyl group is disposed to lie over the piperidine residue, which is in a chair form. A twist between the terminal benzene ring and the hydrazine residue is seen [N-N-C-C torsion angle = 163.81 (12)°]. Helical supra-molecular chains along the c axis mediated by N-H⋯O hydrogen bonds are the most prominent feature of the crystal packing. The chains are connected into layers lying in the ac plane by weak C-H⋯π contacts involving two methyl-ene H atoms and an adjacent benzene ring.

Related literature

For background to the biological activity of amidrazones, see: Frohberg et al. (2006 ▶); Abdel-Aziz & Mekawey (2009 ▶); Abdel-Aziz et al. (2010 ▶). For the synthesis, see: Frohberg et al. (1995 ▶).

Experimental

Crystal data

C14H19N3O

M = 245.32

Orthorhombic,

a = 9.1195 (2) Å

b = 11.9614 (2) Å

c = 12.0393 (2) Å

V = 1313.27 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.64 mm−1

T = 100 K

0.25 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.857, T max = 0.969

5335 measured reflections

2589 independent reflections

2482 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.080

S = 1.05

2589 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1077 Friedel pairs

Flack parameter: −0.1 (3)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029680/hb6327sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029680/hb6327Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029680/hb6327Isup3.cml

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

C14H19N3O	F(000) = 528
Mr = 245.32	Dx = 1.241 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3524 reflections
a = 9.1195 (2) Å	θ = 3.7–73.9°
b = 11.9614 (2) Å	µ = 0.64 mm−1
c = 12.0393 (2) Å	T = 100 K
V = 1313.27 (4) Å3	Prism, yellow
Z = 4	0.25 × 0.10 × 0.05 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	2589 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2482 reflections with I > 2σ(I)
mirror	Rint = 0.021
Detector resolution: 10.4041 pixels mm-1	θmax = 74.1°, θmin = 5.2°
ω scans	h = −11→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→11
Tmin = 0.857, Tmax = 0.969	l = −15→13
5335 measured reflections

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0415P)2 + 0.2381P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2589 reflections	Δρmax = 0.12 e Å−3
168 parameters	Δρmin = −0.20 e Å−3
0 restraints	Absolute structure: Flack (1983), 1077 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.1 (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	0.78315 (11)	0.39621 (8)	0.41136 (8)	0.0206 (2)
N1	0.76810 (12)	0.50948 (9)	0.20177 (9)	0.0152 (2)
N2	0.55012 (12)	0.40406 (10)	0.18282 (10)	0.0161 (2)
N3	0.52865 (13)	0.46113 (10)	0.08925 (10)	0.0176 (2)
C1	0.91802 (15)	0.46592 (12)	0.18446 (12)	0.0180 (3)
H1A	0.9139	0.3963	0.1401	0.022*
H1B	0.9634	0.4482	0.2571	0.022*
C2	1.01007 (16)	0.55293 (12)	0.12398 (12)	0.0212 (3)
H2A	0.9713	0.5632	0.0479	0.025*
H2B	1.1123	0.5258	0.1179	0.025*
C3	1.00881 (16)	0.66502 (12)	0.18456 (13)	0.0221 (3)
H3A	1.0614	0.6576	0.2561	0.027*
H3B	1.0606	0.7216	0.1392	0.027*
C4	0.85187 (16)	0.70368 (12)	0.20604 (13)	0.0219 (3)
H4A	0.8531	0.7729	0.2510	0.026*
H4B	0.8031	0.7205	0.1345	0.026*
C5	0.76669 (16)	0.61340 (11)	0.26713 (12)	0.0201 (3)
H5A	0.8116	0.5999	0.3408	0.024*
H5B	0.6643	0.6382	0.2788	0.024*
C6	0.66729 (15)	0.42747 (11)	0.24015 (11)	0.0159 (3)
C7	0.68611 (15)	0.36763 (12)	0.34649 (11)	0.0172 (3)
C8	0.58735 (18)	0.27024 (12)	0.37224 (12)	0.0236 (3)
H8A	0.5897	0.2550	0.4522	0.035*
H8B	0.6212	0.2041	0.3316	0.035*
H8C	0.4868	0.2882	0.3497	0.035*
C9	0.40458 (15)	0.43897 (11)	0.02405 (11)	0.0158 (3)
C10	0.36359 (15)	0.51634 (12)	−0.05636 (11)	0.0177 (3)
H10	0.4195	0.5825	−0.0668	0.021*
C11	0.24038 (16)	0.49645 (13)	−0.12146 (11)	0.0215 (3)
H11	0.2126	0.5490	−0.1768	0.026*
C12	0.15788 (17)	0.40034 (14)	−0.10604 (12)	0.0246 (3)
H12	0.0731	0.3875	−0.1500	0.030*
C13	0.19957 (17)	0.32311 (13)	−0.02621 (13)	0.0249 (3)
H13	0.1434	0.2570	−0.0160	0.030*
C14	0.32279 (16)	0.34171 (12)	0.03888 (12)	0.0206 (3)
H14	0.3512	0.2884	0.0933	0.025*
H3	0.596 (2)	0.5100 (15)	0.0692 (16)	0.029 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0199 (5)	0.0240 (5)	0.0178 (5)	−0.0002 (4)	−0.0022 (4)	−0.0007 (4)
N1	0.0118 (5)	0.0150 (5)	0.0189 (5)	−0.0006 (4)	0.0002 (4)	−0.0004 (4)
N2	0.0153 (5)	0.0165 (5)	0.0166 (5)	0.0009 (5)	0.0010 (4)	−0.0002 (5)
N3	0.0141 (5)	0.0204 (6)	0.0184 (5)	−0.0045 (5)	−0.0016 (5)	0.0037 (5)
C1	0.0147 (6)	0.0190 (7)	0.0203 (6)	0.0023 (5)	0.0022 (6)	−0.0026 (6)
C2	0.0151 (6)	0.0244 (7)	0.0241 (7)	−0.0003 (6)	0.0043 (6)	0.0018 (6)
C3	0.0162 (7)	0.0221 (7)	0.0280 (7)	−0.0048 (6)	0.0004 (6)	0.0034 (6)
C4	0.0192 (7)	0.0167 (6)	0.0297 (7)	−0.0018 (6)	0.0014 (6)	0.0011 (6)
C5	0.0179 (7)	0.0167 (6)	0.0255 (7)	0.0009 (6)	0.0043 (6)	−0.0022 (6)
C6	0.0141 (6)	0.0156 (6)	0.0178 (6)	−0.0004 (5)	0.0020 (5)	−0.0018 (5)
C7	0.0170 (7)	0.0175 (7)	0.0171 (6)	0.0024 (5)	0.0017 (5)	−0.0029 (5)
C8	0.0299 (8)	0.0211 (7)	0.0199 (7)	−0.0047 (6)	−0.0008 (6)	0.0031 (6)
C9	0.0117 (6)	0.0187 (7)	0.0171 (6)	0.0002 (5)	0.0004 (5)	−0.0039 (5)
C10	0.0154 (6)	0.0203 (6)	0.0175 (6)	0.0000 (5)	0.0019 (5)	−0.0023 (5)
C11	0.0177 (7)	0.0286 (8)	0.0181 (6)	0.0044 (6)	−0.0001 (5)	−0.0019 (6)
C12	0.0156 (6)	0.0342 (8)	0.0241 (7)	−0.0019 (6)	−0.0052 (6)	−0.0072 (6)
C13	0.0192 (7)	0.0248 (7)	0.0307 (8)	−0.0061 (6)	−0.0009 (6)	−0.0047 (6)
C14	0.0180 (7)	0.0191 (7)	0.0247 (7)	−0.0034 (6)	−0.0014 (6)	−0.0006 (6)

O1—C7	1.2288 (17)	C4—H4B	0.9900
N1—C6	1.4216 (17)	C5—H5A	0.9900
N1—C5	1.4712 (17)	C5—H5B	0.9900
N1—C1	1.4778 (17)	C6—C7	1.4767 (19)
N2—C6	1.3025 (18)	C7—C8	1.505 (2)
N2—N3	1.3317 (16)	C8—H8A	0.9800
N3—C9	1.4023 (17)	C8—H8B	0.9800
N3—H3	0.88 (2)	C8—H8C	0.9800
C1—C2	1.523 (2)	C9—C10	1.391 (2)
C1—H1A	0.9900	C9—C14	1.3934 (19)
C1—H1B	0.9900	C10—C11	1.390 (2)
C2—C3	1.526 (2)	C10—H10	0.9500
C2—H2A	0.9900	C11—C12	1.386 (2)
C2—H2B	0.9900	C11—H11	0.9500
C3—C4	1.526 (2)	C12—C13	1.386 (2)
C3—H3A	0.9900	C12—H12	0.9500
C3—H3B	0.9900	C13—C14	1.388 (2)
C4—C5	1.5201 (19)	C13—H13	0.9500
C4—H4A	0.9900	C14—H14	0.9500
C6—N1—C5	113.80 (10)	N1—C5—H5B	109.7
C6—N1—C1	113.63 (10)	C4—C5—H5B	109.7
C5—N1—C1	112.42 (10)	H5A—C5—H5B	108.2
C6—N2—N3	117.31 (11)	N2—C6—N1	120.44 (12)
N2—N3—C9	119.69 (11)	N2—C6—C7	116.78 (12)
N2—N3—H3	118.1 (13)	N1—C6—C7	122.75 (12)
C9—N3—H3	122.1 (13)	O1—C7—C6	119.99 (13)
N1—C1—C2	109.67 (11)	O1—C7—C8	121.03 (12)
N1—C1—H1A	109.7	C6—C7—C8	118.96 (12)
C2—C1—H1A	109.7	C7—C8—H8A	109.5
N1—C1—H1B	109.7	C7—C8—H8B	109.5
C2—C1—H1B	109.7	H8A—C8—H8B	109.5
H1A—C1—H1B	108.2	C7—C8—H8C	109.5
C1—C2—C3	111.58 (12)	H8A—C8—H8C	109.5
C1—C2—H2A	109.3	H8B—C8—H8C	109.5
C3—C2—H2A	109.3	C10—C9—C14	120.06 (13)
C1—C2—H2B	109.3	C10—C9—N3	118.74 (12)
C3—C2—H2B	109.3	C14—C9—N3	121.20 (13)
H2A—C2—H2B	108.0	C11—C10—C9	119.72 (13)
C4—C3—C2	110.75 (12)	C11—C10—H10	120.1
C4—C3—H3A	109.5	C9—C10—H10	120.1
C2—C3—H3A	109.5	C10—C11—C12	120.33 (14)
C4—C3—H3B	109.5	C10—C11—H11	119.8
C2—C3—H3B	109.5	C12—C11—H11	119.8
H3A—C3—H3B	108.1	C13—C12—C11	119.78 (13)
C5—C4—C3	110.24 (12)	C13—C12—H12	120.1
C5—C4—H4A	109.6	C11—C12—H12	120.1
C3—C4—H4A	109.6	C12—C13—C14	120.44 (14)
C5—C4—H4B	109.6	C12—C13—H13	119.8
C3—C4—H4B	109.6	C14—C13—H13	119.8
H4A—C4—H4B	108.1	C13—C14—C9	119.66 (14)
N1—C5—C4	109.69 (11)	C13—C14—H14	120.2
N1—C5—H5A	109.7	C9—C14—H14	120.2
C4—C5—H5A	109.7
C6—N2—N3—C9	179.73 (12)	N2—C6—C7—O1	−170.31 (12)
C6—N1—C1—C2	169.70 (11)	N1—C6—C7—O1	7.84 (19)
C5—N1—C1—C2	−59.23 (15)	N2—C6—C7—C8	11.11 (18)
N1—C1—C2—C3	54.55 (15)	N1—C6—C7—C8	−170.74 (13)
C1—C2—C3—C4	−53.17 (16)	N2—N3—C9—C10	163.81 (12)
C2—C3—C4—C5	54.34 (16)	N2—N3—C9—C14	−16.06 (19)
C6—N1—C5—C4	−167.80 (11)	C14—C9—C10—C11	0.3 (2)
C1—N1—C5—C4	61.21 (15)	N3—C9—C10—C11	−179.57 (12)
C3—C4—C5—N1	−57.74 (16)	C9—C10—C11—C12	0.4 (2)
N3—N2—C6—N1	−1.12 (18)	C10—C11—C12—C13	−0.8 (2)
N3—N2—C6—C7	177.07 (11)	C11—C12—C13—C14	0.4 (2)
C5—N1—C6—N2	108.74 (14)	C12—C13—C14—C9	0.3 (2)
C1—N1—C6—N2	−120.87 (13)	C10—C9—C14—C13	−0.7 (2)
C5—N1—C6—C7	−69.34 (15)	N3—C9—C14—C13	179.22 (13)
C1—N1—C6—C7	61.04 (16)

Cg1 is the centroid of the C9–C14 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.88 (2)	2.47 (2)	3.2317 (15)	145.6 (17)
N3—H3···N1	0.88 (2)	2.242 (19)	2.6340 (16)	106.8 (15)
C2—H2b···Cg1ii	0.99	2.77	3.5535 (16)	137
C3—H3a···Cg1iii	0.99	2.98	3.9473 (16)	167

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.88 (2)	2.47 (2)	3.2317 (15)	145.6 (17)
N3—H3⋯N1	0.88 (2)	2.242 (19)	2.6340 (16)	106.8 (15)
C2—H2b⋯Cg1ii	0.99	2.77	3.5535 (16)	137
C3—H3a⋯Cg1iii	0.99	2.98	3.9473 (16)	167

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