N'-[(2Z)-4-Oxo-4-phenyl-but-2-en-2-yl]pyridine-4-carbohydrazide.

There are significant twists in the title compound, C(16)H(15)N(3)O(2), as seen in the dihedral angle between the benzene and adjacent but-2-enal group [29.26 (4)°] and between the pyridine ring and amide group [24.79 (6)°]. A twist is also evident around the hydrazine bond [the C-N-N-C torsion angle is -138.25 (13)°]. The conformation about the ethene bond is Z. An intra-molecular N-H⋯O hydrogen bond involving the benzoyl O atom and leading to an S(6) motif is formed. Significant delocalization of π-electron density is found in this part of the mol-ecule. In the crystal, helical supra-molecular chains aligned along the b axis and mediated by N-H⋯O hydrogen bonds are formed.

Related literature

For the structures of related carbohydrazides, see: Bikas et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C16H15N3O2

M = 281.31

Monoclinic,

a = 15.7640 (4) Å

b = 6.5194 (1) Å

c = 13.3093 (3) Å

β = 93.579 (2)°

V = 1365.15 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.76 mm−1

T = 100 K

0.20 × 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 = 0.864, T max = 0.963

5321 measured reflections

2808 independent reflections

2397 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.02

2808 reflections

199 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000529/hg5158sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000529/hg5158Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000529/hg5158Isup3.cml

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

C16H15N3O2	F(000) = 592
Mr = 281.31	Dx = 1.369 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 2202 reflections
a = 15.7640 (4) Å	θ = 2.8–76.4°
b = 6.5194 (1) Å	µ = 0.76 mm−1
c = 13.3093 (3) Å	T = 100 K
β = 93.579 (2)°	Prism, colourless
V = 1365.15 (5) Å3	0.20 × 0.10 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2808 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2397 reflections with I > 2σ(I)
Mirror	Rint = 0.022
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 2.8°
ω scan	h = −14→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −8→4
Tmin = 0.864, Tmax = 0.963	l = −13→16
5321 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.4474P] where P = (Fo2 + 2Fc2)/3
2808 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.64472 (6)	0.16395 (15)	0.10581 (7)	0.0222 (2)
O2	0.39259 (6)	0.19577 (14)	0.15136 (7)	0.0192 (2)
N1	0.93135 (7)	0.45503 (19)	0.21632 (9)	0.0244 (3)
N2	0.61169 (7)	0.47152 (17)	0.17399 (9)	0.0182 (2)
N3	0.52548 (7)	0.43426 (17)	0.15465 (8)	0.0176 (2)
C1	0.75840 (8)	0.3754 (2)	0.17323 (9)	0.0170 (3)
C2	0.81664 (9)	0.2161 (2)	0.18446 (10)	0.0215 (3)
H2A	0.7986	0.0775	0.1773	0.026*
C3	0.90178 (9)	0.2629 (2)	0.20629 (11)	0.0249 (3)
H3A	0.9411	0.1529	0.2145	0.030*
C4	0.87448 (9)	0.6070 (2)	0.20366 (10)	0.0225 (3)
H4	0.8945	0.7442	0.2095	0.027*
C5	0.78809 (8)	0.5759 (2)	0.18252 (10)	0.0194 (3)
H5	0.7502	0.6888	0.1746	0.023*
C6	0.66681 (8)	0.3232 (2)	0.14810 (9)	0.0168 (3)
C7	0.47294 (8)	0.58056 (19)	0.11764 (9)	0.0170 (3)
C8	0.50980 (8)	0.7859 (2)	0.09507 (10)	0.0197 (3)
H8A	0.5348	0.8469	0.1574	0.030*
H8B	0.4648	0.8758	0.0661	0.030*
H8C	0.5539	0.7695	0.0470	0.030*
C9	0.38667 (8)	0.5408 (2)	0.09966 (10)	0.0174 (3)
H9	0.3508	0.6492	0.0753	0.021*
C10	0.34988 (8)	0.3474 (2)	0.11585 (9)	0.0166 (3)
C11	0.25751 (8)	0.3125 (2)	0.08761 (9)	0.0173 (3)
C12	0.19729 (8)	0.4687 (2)	0.08987 (10)	0.0204 (3)
H12	0.2147	0.6046	0.1066	0.025*
C13	0.11164 (9)	0.4262 (2)	0.06766 (11)	0.0251 (3)
H13	0.0706	0.5322	0.0711	0.030*
C14	0.08620 (9)	0.2289 (2)	0.04045 (11)	0.0260 (3)
H14	0.0277	0.2003	0.0250	0.031*
C15	0.14599 (9)	0.0735 (2)	0.03576 (11)	0.0248 (3)
H15	0.1286	−0.0610	0.0163	0.030*
C16	0.23130 (9)	0.1148 (2)	0.05958 (10)	0.0209 (3)
H16	0.2721	0.0080	0.0568	0.025*
H2	0.6210 (11)	0.549 (3)	0.2275 (14)	0.029 (5)*
H3	0.5045 (11)	0.308 (3)	0.1636 (13)	0.028 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0214 (5)	0.0160 (5)	0.0288 (5)	−0.0010 (4)	−0.0021 (4)	−0.0039 (4)
O2	0.0180 (4)	0.0157 (5)	0.0239 (5)	0.0014 (3)	0.0007 (4)	0.0039 (4)
N1	0.0184 (6)	0.0260 (6)	0.0289 (6)	−0.0015 (5)	0.0014 (5)	−0.0019 (5)
N2	0.0150 (5)	0.0182 (5)	0.0213 (6)	−0.0014 (4)	−0.0003 (4)	−0.0038 (4)
N3	0.0146 (5)	0.0158 (5)	0.0224 (5)	−0.0007 (4)	0.0006 (4)	0.0004 (4)
C1	0.0171 (6)	0.0179 (6)	0.0159 (6)	−0.0012 (5)	0.0009 (5)	−0.0004 (5)
C2	0.0205 (6)	0.0171 (6)	0.0268 (7)	0.0007 (5)	0.0009 (5)	0.0007 (5)
C3	0.0198 (7)	0.0235 (7)	0.0312 (7)	0.0024 (5)	0.0006 (6)	0.0009 (6)
C4	0.0219 (7)	0.0197 (7)	0.0261 (7)	−0.0038 (5)	0.0028 (5)	−0.0020 (5)
C5	0.0198 (6)	0.0173 (6)	0.0214 (6)	−0.0004 (5)	0.0024 (5)	−0.0006 (5)
C6	0.0183 (6)	0.0155 (6)	0.0165 (6)	−0.0001 (5)	0.0011 (5)	0.0017 (5)
C7	0.0204 (6)	0.0147 (6)	0.0159 (6)	0.0009 (5)	0.0021 (5)	−0.0006 (5)
C8	0.0210 (6)	0.0152 (6)	0.0231 (6)	−0.0009 (5)	0.0017 (5)	0.0008 (5)
C9	0.0180 (6)	0.0160 (6)	0.0183 (6)	0.0022 (5)	0.0015 (5)	0.0010 (5)
C10	0.0177 (6)	0.0163 (6)	0.0160 (6)	0.0024 (5)	0.0030 (5)	0.0007 (5)
C11	0.0168 (6)	0.0189 (6)	0.0162 (6)	−0.0006 (5)	0.0016 (5)	0.0016 (5)
C12	0.0193 (6)	0.0194 (6)	0.0227 (6)	0.0013 (5)	0.0019 (5)	0.0009 (5)
C13	0.0189 (7)	0.0277 (7)	0.0289 (7)	0.0043 (5)	0.0026 (5)	0.0020 (6)
C14	0.0170 (6)	0.0323 (8)	0.0284 (7)	−0.0037 (5)	−0.0012 (5)	0.0018 (6)
C15	0.0237 (7)	0.0233 (7)	0.0271 (7)	−0.0050 (5)	0.0003 (5)	−0.0014 (6)
C16	0.0209 (7)	0.0196 (7)	0.0223 (6)	0.0003 (5)	0.0024 (5)	0.0000 (5)

O1—C6	1.2213 (16)	C7—C8	1.4973 (17)
O2—C10	1.2705 (15)	C8—H8A	0.9800
N1—C4	1.3395 (18)	C8—H8B	0.9800
N1—C3	1.3401 (18)	C8—H8C	0.9800
N2—C6	1.3587 (17)	C9—C10	1.4097 (18)
N2—N3	1.3887 (15)	C9—H9	0.9500
N2—H2	0.878 (18)	C10—C11	1.4984 (17)
N3—C7	1.3369 (16)	C11—C12	1.3938 (18)
N3—H3	0.899 (18)	C11—C16	1.3974 (19)
C1—C2	1.3884 (18)	C12—C13	1.3918 (18)
C1—C5	1.3914 (18)	C12—H12	0.9500
C1—C6	1.5006 (17)	C13—C14	1.389 (2)
C2—C3	1.3894 (19)	C13—H13	0.9500
C2—H2A	0.9500	C14—C15	1.388 (2)
C3—H3A	0.9500	C14—H14	0.9500
C4—C5	1.3882 (19)	C15—C16	1.3887 (19)
C4—H4	0.9500	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C7—C9	1.3905 (18)
C4—N1—C3	116.92 (12)	C7—C8—H8B	109.5
C6—N2—N3	117.55 (11)	H8A—C8—H8B	109.5
C6—N2—H2	122.5 (11)	C7—C8—H8C	109.5
N3—N2—H2	111.3 (11)	H8A—C8—H8C	109.5
C7—N3—N2	121.34 (11)	H8B—C8—H8C	109.5
C7—N3—H3	118.6 (11)	C7—C9—C10	123.22 (12)
N2—N3—H3	120.0 (11)	C7—C9—H9	118.4
C2—C1—C5	118.48 (12)	C10—C9—H9	118.4
C2—C1—C6	118.35 (12)	O2—C10—C9	122.62 (12)
C5—C1—C6	123.13 (12)	O2—C10—C11	117.35 (11)
C1—C2—C3	118.80 (13)	C9—C10—C11	120.00 (11)
C1—C2—H2A	120.6	C12—C11—C16	119.30 (12)
C3—C2—H2A	120.6	C12—C11—C10	122.43 (12)
N1—C3—C2	123.49 (13)	C16—C11—C10	118.26 (12)
N1—C3—H3A	118.3	C13—C12—C11	120.19 (13)
C2—C3—H3A	118.3	C13—C12—H12	119.9
N1—C4—C5	123.92 (13)	C11—C12—H12	119.9
N1—C4—H4	118.0	C14—C13—C12	120.03 (13)
C5—C4—H4	118.0	C14—C13—H13	120.0
C4—C5—C1	118.39 (12)	C12—C13—H13	120.0
C4—C5—H5	120.8	C15—C14—C13	120.13 (13)
C1—C5—H5	120.8	C15—C14—H14	119.9
O1—C6—N2	123.60 (12)	C13—C14—H14	119.9
O1—C6—C1	122.56 (12)	C16—C15—C14	119.93 (13)
N2—C6—C1	113.82 (11)	C16—C15—H15	120.0
N3—C7—C9	120.46 (12)	C14—C15—H15	120.0
N3—C7—C8	118.20 (11)	C15—C16—C11	120.38 (13)
C9—C7—C8	121.33 (11)	C15—C16—H16	119.8
C7—C8—H8A	109.5	C11—C16—H16	119.8
C6—N2—N3—C7	−138.25 (13)	N3—C7—C9—C10	−1.89 (19)
C5—C1—C2—C3	1.2 (2)	C8—C7—C9—C10	177.29 (12)
C6—C1—C2—C3	179.09 (12)	C7—C9—C10—O2	2.3 (2)
C4—N1—C3—C2	−0.4 (2)	C7—C9—C10—C11	−175.56 (11)
C1—C2—C3—N1	−0.6 (2)	O2—C10—C11—C12	151.66 (13)
C3—N1—C4—C5	0.9 (2)	C9—C10—C11—C12	−30.34 (18)
N1—C4—C5—C1	−0.4 (2)	O2—C10—C11—C16	−27.33 (17)
C2—C1—C5—C4	−0.68 (19)	C9—C10—C11—C16	150.67 (12)
C6—C1—C5—C4	−178.49 (12)	C16—C11—C12—C13	2.1 (2)
N3—N2—C6—O1	2.78 (19)	C10—C11—C12—C13	−176.86 (12)
N3—N2—C6—C1	−179.11 (10)	C11—C12—C13—C14	−1.8 (2)
C2—C1—C6—O1	−24.59 (19)	C12—C13—C14—C15	0.3 (2)
C5—C1—C6—O1	153.23 (13)	C13—C14—C15—C16	0.8 (2)
C2—C1—C6—N2	157.27 (12)	C14—C15—C16—C11	−0.5 (2)
C5—C1—C6—N2	−24.91 (18)	C12—C11—C16—C15	−1.0 (2)
N2—N3—C7—C9	−179.40 (11)	C10—C11—C16—C15	178.01 (12)
N2—N3—C7—C8	1.39 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.88 (2)	1.90 (2)	2.750 (2)	163 (2)
N3—H3···O2	0.90 (2)	1.91 (2)	2.607 (1)	133 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.88 (2)	1.90 (2)	2.750 (2)	163 (2)
N3—H3⋯O2	0.90 (2)	1.91 (2)	2.607 (1)	133 (2)

Symmetry code: (i) .