organic compounds
(E)-2-(4-Chlorophenoxy)-N′-(pyridin-4-ylmethylidene)acetohydrazide
aCollege of Materials Science and Engineering, Huaqiao University, Xiamen, Fujian 361021, People's Republic of China
*Correspondence e-mail: wws@hqu.edu.cn
In the title compound, C14H12ClN3O2, the acylhydrazone base [C(=O)—N—N=C] is essentially planar, with an r.m.s. deviation of 0.0095 Å, and makes a dihedral angle of 12.52 (10)°with the pyridine ring. In the crystal, molecules are linked via pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R22(8) graph-set motif. The dimers are linked via C—H⋯π interactions forming chains along [101].
Related literature
For chemical properties of et al. (2005); Liu et al. (2006). For the synthesis and structure of ethyl(4-chlorophenoxy)acetate, see: Dutkiewicz et al. (2009). For graph-set motifs, see: Etter et al. (1990) and for classification of hydrogen bonds, see: Gilli & Gilli (2009).
see: NarayanaExperimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1999); cell SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536812045989/fb2275sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812045989/fb2275Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812045989/fb2275Isup3.cml
The synthesis of the title structure proceeded in three steps.
First, concentrated H2SO4 (98 weight %, 1.4 ml) was added slowly while stirring to a mixture of 4-chlorophenoxyacetic acid (11.2 g, 0.06 mol) in ethanol (99.7 volume %, 120 ml). The mixture was left to reflux for 6 h at 359 K. Then 34.2 ml of 98.5 weight % of tris(2-hydroxyethyl)amine (trolamine) were added dropwise into the mixture while stirring in order to neutralize the mixture. Then the ethanol in the mixture was removed by reduced pressure distillation (335 K, about 0.003 MPa). What has left was poured into 100 ml of water heated to 321 K. The white precipitate (12.21 g) of ethyl(4-chlorophenoxy)acetate was filtered and washed.
Second step consisted in the synthesis of 2-(4-chlorophenoxy)acetohydrazide. It was carried out according to the method applied by Dutkiewicz et al. (2009). A mixture of ethyl(4-chlorophenoxy)acetate (8.56 g, 0.04 mol) and 50 ml of hydrazine hydrate (85 weight %) was refluxed over water bath for 5 h at 365 K. The precipitate was filtered off and recrystallized from ethanol (99.7 volume %) yielding plate-like colourless crystals of 2-(4-chlorophenoxy)acetohydrazide.
Finally, the title compound was synthesized by adding 4-pyridinecarboxaldehyde (5 ml) slowly to a mixture of 2-(4-chlorophenoxy) acetohydrazide in ethanol (99.7 volume %, 20 ml) and water (15 ml) while stirring. Then the mixture was refluxed for 3.5 h at room temperature. Prismatic colourless crystals with the size about that of the used sample formed in 24 h.
All the hydrogen atoms were identified in the difference
nevertheless the aryl and methylene H atoms were situated into idealized positions and constrained to ride on their parent atoms with C—H = 0.93 and 0.97 Å for aryl and methylene H atoms, respectively, with Uiso(Haryl/methylene) = 1.2Ueq(Caryl/methylene). The positional parameters of the secondary amine H atom were refined freely while its isotropic displacement parameter was constrained as 1.2 multiple of the equivalent isotropic parameter of its carrier atom.Hydrazides usually serve as precursors in the synthesis of several heterocyclic systems (Narayana et al., 2005). Some substituted
are used as intermediates in many pharmaceutically important compounds (Liu et al., 2006). A new hydrazide, (E)-2-(4-chlorophenoxy)-N'-(pyridin-4-ylmethylene)acetohydrazide, C14H12Cl1O2N3, has been synthesized and its is reported here (Fig. 1).In the title molecule, the principal cohesion interactions are N—H···O hydrogen bonds of moderate strength (Gilli & Gilli, 2009) which link the molecules into a dimer with the graph-set motif (Etter et al., 1990) R22(8) (Tab. 1). Moreover, there are present C—H···π-electron ring interactions in the structure (Fig. 2). The acylhydrazone base is essentially planar with the r.m.s. deviation from planarity which equals to 0.0095 Å. The pyridine ring and the acylhydrazone base [C1(═O1)—N1—N2═C9] contain the angle 12.52 (10)°.
For chemical properties of
see: Narayana et al. (2005); Liu et al. (2006). For the synthesis and structure of ethyl(4-chlorophenoxy)acetate, see: Dutkiewicz et al. (2009). For graph-set motifs, see: Etter et al. (1990) and for classification of hydrogen bonds, see: Gilli & Gilli (2009).Data collection: SMART (Bruker, 1999); cell
SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C14H12ClN3O2 | F(000) = 600 |
Mr = 289.72 | Dx = 1.482 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3317 reflections |
a = 13.059 (4) Å | θ = 2.2–27.9° |
b = 5.3567 (16) Å | µ = 0.30 mm−1 |
c = 19.175 (6) Å | T = 173 K |
β = 104.586 (5)° | Prism, colourless |
V = 1298.2 (7) Å3 | 0.53 × 0.21 × 0.14 mm |
Z = 4 |
Bruker SMART APEX diffractometer | 2796 independent reflections |
Radiation source: fine-focus sealed tube | 2437 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.927, Tmax = 0.959 | k = −6→6 |
7114 measured reflections | l = −24→15 |
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)] = 0.041 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.037P)2 + 0.573P] where P = (Fo2 + 2Fc2)/3 |
2796 reflections | (Δ/σ)max < 0.001 |
184 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
45 constraints |
C14H12ClN3O2 | V = 1298.2 (7) Å3 |
Mr = 289.72 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.059 (4) Å | µ = 0.30 mm−1 |
b = 5.3567 (16) Å | T = 173 K |
c = 19.175 (6) Å | 0.53 × 0.21 × 0.14 mm |
β = 104.586 (5)° |
Bruker SMART APEX diffractometer | 2796 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2437 reflections with I > 2σ(I) |
Tmin = 0.927, Tmax = 0.959 | Rint = 0.033 |
7114 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.27 e Å−3 |
2796 reflections | Δρmin = −0.24 e Å−3 |
184 parameters |
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 | ||
C1 | 0.07691 (12) | 1.4108 (3) | 0.10391 (8) | 0.0216 (3) | |
C2 | 0.12993 (12) | 1.3618 (3) | 0.18254 (8) | 0.0244 (3) | |
H2A | 0.0959 | 1.4606 | 0.2127 | 0.029* | |
H2B | 0.1224 | 1.1870 | 0.1934 | 0.029* | |
C3 | 0.29987 (12) | 1.2712 (3) | 0.16797 (8) | 0.0210 (3) | |
C4 | 0.40322 (12) | 1.3495 (3) | 0.17631 (8) | 0.0242 (3) | |
H4A | 0.4260 | 1.4979 | 0.2004 | 0.029* | |
C5 | 0.47256 (13) | 1.2089 (3) | 0.14905 (9) | 0.0269 (4) | |
H5A | 0.5420 | 1.2616 | 0.1545 | 0.032* | |
C6 | 0.43774 (13) | 0.9893 (3) | 0.11357 (9) | 0.0267 (4) | |
C7 | 0.33550 (13) | 0.9090 (3) | 0.10505 (8) | 0.0262 (4) | |
H7A | 0.3130 | 0.7607 | 0.0808 | 0.031* | |
C8 | 0.26625 (12) | 1.0497 (3) | 0.13270 (8) | 0.0230 (3) | |
H8A | 0.1971 | 0.9953 | 0.1276 | 0.028* | |
C9 | −0.12003 (12) | 0.9586 (3) | 0.06945 (8) | 0.0236 (3) | |
H9A | −0.1455 | 0.9987 | 0.0210 | 0.028* | |
C10 | −0.28617 (13) | 0.4072 (3) | 0.08435 (9) | 0.0287 (4) | |
H10A | −0.3333 | 0.3023 | 0.0532 | 0.034* | |
C11 | −0.24060 (12) | 0.5978 (3) | 0.05463 (9) | 0.0262 (4) | |
H11A | −0.2573 | 0.6204 | 0.0050 | 0.031* | |
C12 | −0.16955 (12) | 0.7556 (3) | 0.09964 (8) | 0.0231 (3) | |
C13 | −0.14931 (14) | 0.7123 (4) | 0.17301 (9) | 0.0326 (4) | |
H13A | −0.1027 | 0.8143 | 0.2054 | 0.039* | |
C14 | −0.19892 (15) | 0.5172 (4) | 0.19725 (10) | 0.0368 (4) | |
H14A | −0.1840 | 0.4903 | 0.2467 | 0.044* | |
Cl1 | 0.52572 (4) | 0.80977 (9) | 0.08079 (3) | 0.04032 (16) | |
N1 | −0.00592 (10) | 1.2696 (3) | 0.07166 (7) | 0.0233 (3) | |
H1A | −0.0369 (15) | 1.304 (4) | 0.0261 (10) | 0.028* | |
N2 | −0.04318 (10) | 1.0820 (3) | 0.10753 (7) | 0.0232 (3) | |
N3 | −0.26732 (11) | 0.3633 (3) | 0.15439 (8) | 0.0308 (3) | |
O1 | 0.10839 (9) | 1.5774 (2) | 0.07075 (6) | 0.0277 (3) | |
O2 | 0.23832 (8) | 1.4241 (2) | 0.19755 (6) | 0.0237 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0174 (7) | 0.0246 (9) | 0.0239 (7) | 0.0029 (6) | 0.0071 (6) | −0.0003 (6) |
C2 | 0.0182 (7) | 0.0337 (9) | 0.0218 (7) | −0.0036 (7) | 0.0060 (6) | −0.0021 (7) |
C3 | 0.0208 (8) | 0.0261 (8) | 0.0147 (7) | −0.0005 (6) | 0.0022 (6) | 0.0038 (6) |
C4 | 0.0219 (8) | 0.0257 (9) | 0.0233 (7) | −0.0037 (6) | 0.0028 (6) | 0.0009 (6) |
C5 | 0.0187 (8) | 0.0312 (9) | 0.0307 (8) | −0.0020 (7) | 0.0063 (6) | 0.0073 (7) |
C6 | 0.0253 (8) | 0.0289 (9) | 0.0274 (8) | 0.0077 (7) | 0.0095 (6) | 0.0069 (7) |
C7 | 0.0281 (8) | 0.0244 (9) | 0.0237 (8) | 0.0006 (7) | 0.0023 (6) | 0.0009 (6) |
C8 | 0.0187 (7) | 0.0258 (9) | 0.0224 (7) | −0.0021 (6) | 0.0015 (6) | 0.0040 (6) |
C9 | 0.0200 (7) | 0.0278 (9) | 0.0228 (7) | 0.0012 (6) | 0.0048 (6) | 0.0006 (6) |
C10 | 0.0232 (8) | 0.0305 (10) | 0.0335 (9) | −0.0046 (7) | 0.0093 (7) | −0.0074 (7) |
C11 | 0.0225 (8) | 0.0317 (10) | 0.0251 (8) | −0.0006 (7) | 0.0076 (6) | −0.0033 (7) |
C12 | 0.0175 (7) | 0.0260 (9) | 0.0266 (8) | 0.0004 (6) | 0.0072 (6) | −0.0007 (6) |
C13 | 0.0308 (9) | 0.0391 (11) | 0.0260 (8) | −0.0120 (8) | 0.0036 (7) | −0.0024 (7) |
C14 | 0.0384 (10) | 0.0454 (12) | 0.0269 (9) | −0.0093 (9) | 0.0087 (7) | 0.0041 (8) |
Cl1 | 0.0365 (3) | 0.0378 (3) | 0.0524 (3) | 0.0111 (2) | 0.0219 (2) | 0.0032 (2) |
N1 | 0.0197 (7) | 0.0277 (8) | 0.0214 (7) | −0.0029 (6) | 0.0032 (5) | 0.0041 (6) |
N2 | 0.0184 (6) | 0.0262 (7) | 0.0261 (7) | −0.0011 (5) | 0.0074 (5) | 0.0019 (5) |
N3 | 0.0269 (7) | 0.0316 (8) | 0.0358 (8) | −0.0040 (6) | 0.0115 (6) | 0.0008 (6) |
O1 | 0.0238 (6) | 0.0315 (7) | 0.0260 (6) | −0.0056 (5) | 0.0029 (5) | 0.0043 (5) |
O2 | 0.0176 (5) | 0.0304 (6) | 0.0227 (5) | −0.0028 (5) | 0.0042 (4) | −0.0048 (5) |
C1—O1 | 1.2251 (19) | C8—H8A | 0.9300 |
C1—N1 | 1.337 (2) | C9—N2 | 1.268 (2) |
C1—C2 | 1.515 (2) | C9—C12 | 1.458 (2) |
C2—O2 | 1.4117 (18) | C9—H9A | 0.9300 |
C2—H2A | 0.9700 | C10—N3 | 1.324 (2) |
C2—H2B | 0.9700 | C10—C11 | 1.376 (2) |
C3—O2 | 1.3667 (19) | C10—H10A | 0.9300 |
C3—C8 | 1.382 (2) | C11—C12 | 1.385 (2) |
C3—C4 | 1.384 (2) | C11—H11A | 0.9300 |
C4—C5 | 1.378 (2) | C12—C13 | 1.384 (2) |
C4—H4A | 0.9300 | C13—C14 | 1.371 (3) |
C5—C6 | 1.378 (3) | C13—H13A | 0.9300 |
C5—H5A | 0.9300 | C14—N3 | 1.335 (2) |
C6—C7 | 1.373 (2) | C14—H14A | 0.9300 |
C6—Cl1 | 1.7331 (17) | N1—N2 | 1.3740 (19) |
C7—C8 | 1.381 (2) | N1—H1A | 0.885 (19) |
C7—H7A | 0.9300 | ||
O1—C1—N1 | 120.66 (14) | C3—C8—H8A | 120.1 |
O1—C1—C2 | 120.91 (14) | N2—C9—C12 | 121.74 (14) |
N1—C1—C2 | 118.43 (14) | N2—C9—H9A | 119.1 |
O2—C2—C1 | 110.20 (12) | C12—C9—H9A | 119.1 |
O2—C2—H2A | 109.6 | N3—C10—C11 | 124.23 (16) |
C1—C2—H2A | 109.6 | N3—C10—H10A | 117.9 |
O2—C2—H2B | 109.6 | C11—C10—H10A | 117.9 |
C1—C2—H2B | 109.6 | C10—C11—C12 | 119.14 (15) |
H2A—C2—H2B | 108.1 | C10—C11—H11A | 120.4 |
O2—C3—C8 | 124.76 (14) | C12—C11—H11A | 120.4 |
O2—C3—C4 | 115.40 (14) | C13—C12—C11 | 117.25 (16) |
C8—C3—C4 | 119.83 (15) | C13—C12—C9 | 122.58 (15) |
C5—C4—C3 | 120.37 (16) | C11—C12—C9 | 120.17 (14) |
C5—C4—H4A | 119.8 | C14—C13—C12 | 119.13 (16) |
C3—C4—H4A | 119.8 | C14—C13—H13A | 120.4 |
C6—C5—C4 | 119.18 (15) | C12—C13—H13A | 120.4 |
C6—C5—H5A | 120.4 | N3—C14—C13 | 124.18 (16) |
C4—C5—H5A | 120.4 | N3—C14—H14A | 117.9 |
C7—C6—C5 | 121.09 (15) | C13—C14—H14A | 117.9 |
C7—C6—Cl1 | 119.78 (14) | C1—N1—N2 | 121.96 (14) |
C5—C6—Cl1 | 119.11 (13) | C1—N1—H1A | 117.0 (12) |
C6—C7—C8 | 119.65 (16) | N2—N1—H1A | 121.1 (12) |
C6—C7—H7A | 120.2 | C9—N2—N1 | 114.93 (14) |
C8—C7—H7A | 120.2 | C10—N3—C14 | 116.08 (15) |
C7—C8—C3 | 119.88 (15) | C3—O2—C2 | 115.99 (12) |
C7—C8—H8A | 120.1 | ||
O1—C1—C2—O2 | −30.5 (2) | N2—C9—C12—C13 | 11.5 (3) |
N1—C1—C2—O2 | 150.25 (14) | N2—C9—C12—C11 | −169.00 (16) |
O2—C3—C4—C5 | 179.56 (13) | C11—C12—C13—C14 | 0.6 (3) |
C8—C3—C4—C5 | 0.6 (2) | C9—C12—C13—C14 | −179.92 (17) |
C3—C4—C5—C6 | −0.2 (2) | C12—C13—C14—N3 | −0.4 (3) |
C4—C5—C6—C7 | 0.0 (2) | O1—C1—N1—N2 | −179.81 (14) |
C4—C5—C6—Cl1 | −178.81 (12) | C2—C1—N1—N2 | −0.5 (2) |
C5—C6—C7—C8 | −0.3 (2) | C12—C9—N2—N1 | −179.18 (14) |
Cl1—C6—C7—C8 | 178.51 (12) | C1—N1—N2—C9 | −177.82 (15) |
C6—C7—C8—C3 | 0.7 (2) | C11—C10—N3—C14 | −0.3 (3) |
O2—C3—C8—C7 | −179.75 (14) | C13—C14—N3—C10 | 0.3 (3) |
C4—C3—C8—C7 | −0.9 (2) | C8—C3—O2—C2 | −8.0 (2) |
N3—C10—C11—C12 | 0.5 (3) | C4—C3—O2—C2 | 173.13 (13) |
C10—C11—C12—C13 | −0.6 (2) | C1—C2—O2—C3 | −69.79 (17) |
C10—C11—C12—C9 | 179.86 (15) |
Cg2 is the centroid of the C3–C8 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.885 (19) | 1.96 (2) | 2.8423 (19) | 172.9 (18) |
C2—H2A···Cg2ii | 0.97 | 2.88 | 3.676 (2) | 140 |
Symmetry codes: (i) −x, −y+3, −z; (ii) −x+1/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H12ClN3O2 |
Mr | 289.72 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 13.059 (4), 5.3567 (16), 19.175 (6) |
β (°) | 104.586 (5) |
V (Å3) | 1298.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.53 × 0.21 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART APEX |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.927, 0.959 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7114, 2796, 2437 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.638 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.104, 1.05 |
No. of reflections | 2796 |
No. of parameters | 184 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.24 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cg2 is the centroid of the C3–C8 phenyl ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.885 (19) | 1.96 (2) | 2.8423 (19) | 172.9 (18) |
C2—H2A···Cg2ii | 0.97 | 2.88 | 3.676 (2) | 140.0 |
Symmetry codes: (i) −x, −y+3, −z; (ii) −x+1/2, y+1/2, −z+1/2. |
Acknowledgements
We are grateful for financial support from the National Science Foundation of Fujian Province of China (No. 2010 J01288) and the Fundamental Research Funds for the Central Universities (No. JB-JC1003). We also thank Dr Zhan-bin Wei (Department of Chemistry, Xiamen University) for the data collection.
References
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Hydrazides usually serve as precursors in the synthesis of several heterocyclic systems (Narayana et al., 2005). Some substituted hydrazides are used as intermediates in many pharmaceutically important compounds (Liu et al., 2006). A new hydrazide, (E)-2-(4-chlorophenoxy)-N'-(pyridin-4-ylmethylene)acetohydrazide, C14H12Cl1O2N3, has been synthesized and its crystal structure is reported here (Fig. 1).
In the title molecule, the principal cohesion interactions are N—H···O hydrogen bonds of moderate strength (Gilli & Gilli, 2009) which link the molecules into a dimer with the graph-set motif (Etter et al., 1990) R22(8) (Tab. 1). Moreover, there are present C—H···π-electron ring interactions in the structure (Fig. 2). The acylhydrazone base is essentially planar with the r.m.s. deviation from planarity which equals to 0.0095 Å. The pyridine ring and the acylhydrazone base [C1(═O1)—N1—N2═C9] contain the angle 12.52 (10)°.