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organic compounds
2-Phenyl-N′-(2-phenylacetyl)acetohydrazide
aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
In the title compound, C16H16N2O2, the N′-acetylacetohydrazide group is approximately planar (r.m.s. deviation = 0.018 Å for the eight non-H atoms) and makes dihedral angles of 81.92 (6) and 65.19 (6)° with the terminal phenyl rings. The phenyl rings form a dihedral angle of 62.60 (7)°. In the crystal, molecules are linked into sheets lying parallel to (001) by N—H⋯O and C—H⋯O hydrogen bonds. One O atom accepts one N—H⋯O and one C—H⋯O hydrogen bond and the other O atom accepts one N—H⋯O and two C—H⋯O hydrogen bonds. The N—H⋯O hydrogen bonds lead to R22(8) loops and the C—H⋯O hydrogen bonds generate R21(6) loops.
Related literature
For general background to and the pharmaceutical applications of hydrazine derivatives, see: Bredihhin & Mäeorg (2008); Ragnarsson (2001
); Ling et al. (2001
). For further synthesis details, see: Magedov & Smushkevich (1991
). For standard bond-length data, see: Allen et al. (1987
). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986
). For hydrogen-bond motifs, see: Bernstein et al. (1995
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009
); 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, 2009
).
Supporting information
10.1107/S1600536812019861/hb6773sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812019861/hb6773Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812019861/hb6773Isup3.cml
The title compound was prepared by the reaction of 2-phenylacetyl chloride with 2-phenylacetohydrazide in the presence of sodium carbonate in water at 5-10 °C (Magedov & Smushkevich, 1991).
All H atoms were located in a difference Fourier map and refined freely with N–H = 0.869 (18)-0.908 (19) Å and C–H = 0.942 (19)-1.013 (18) Å.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).C16H16N2O2 | Z = 2 |
Mr = 268.31 | F(000) = 284 |
Triclinic, P1 | Dx = 1.364 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.4531 (6) Å | Cell parameters from 3410 reflections |
b = 7.9283 (9) Å | θ = 4.0–30.0° |
c = 15.1758 (17) Å | µ = 0.09 mm−1 |
α = 94.271 (2)° | T = 100 K |
β = 92.613 (2)° | Needle, colourless |
γ = 90.830 (2)° | 0.35 × 0.14 × 0.05 mm |
V = 653.50 (13) Å3 |
Bruker SMART APEXII DUO CCD diffractometer | 3458 independent reflections |
Radiation source: fine-focus sealed tube | 2428 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ϕ and ω scans | θmax = 29.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −7→7 |
Tmin = 0.968, Tmax = 0.996 | k = −10→10 |
12991 measured reflections | l = −20→20 |
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: inferred from neighbouring sites |
wR(F2) = 0.134 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0709P)2 + 0.1901P] where P = (Fo2 + 2Fc2)/3 |
3458 reflections | (Δ/σ)max = 0.001 |
245 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C16H16N2O2 | γ = 90.830 (2)° |
Mr = 268.31 | V = 653.50 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.4531 (6) Å | Mo Kα radiation |
b = 7.9283 (9) Å | µ = 0.09 mm−1 |
c = 15.1758 (17) Å | T = 100 K |
α = 94.271 (2)° | 0.35 × 0.14 × 0.05 mm |
β = 92.613 (2)° |
Bruker SMART APEXII DUO CCD diffractometer | 3458 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2428 reflections with I > 2σ(I) |
Tmin = 0.968, Tmax = 0.996 | Rint = 0.030 |
12991 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.134 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.38 e Å−3 |
3458 reflections | Δρmin = −0.29 e Å−3 |
245 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
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 | ||
O1 | 0.40065 (18) | 0.64320 (12) | 0.06665 (6) | 0.0165 (2) | |
O2 | 1.08994 (18) | 0.85895 (12) | −0.07188 (6) | 0.0166 (2) | |
N1 | 0.7067 (2) | 0.81353 (14) | 0.02864 (7) | 0.0131 (2) | |
N2 | 0.7869 (2) | 0.68791 (14) | −0.03185 (7) | 0.0136 (2) | |
C1 | 0.2796 (3) | 0.94134 (17) | 0.29275 (9) | 0.0154 (3) | |
C2 | 0.3026 (3) | 0.90738 (18) | 0.38118 (9) | 0.0185 (3) | |
C3 | 0.4978 (3) | 0.81340 (18) | 0.41175 (9) | 0.0184 (3) | |
C4 | 0.6710 (3) | 0.75379 (18) | 0.35344 (9) | 0.0180 (3) | |
C5 | 0.6502 (2) | 0.78955 (17) | 0.26515 (9) | 0.0153 (3) | |
C6 | 0.4540 (2) | 0.88282 (16) | 0.23362 (8) | 0.0127 (3) | |
C7 | 0.4336 (3) | 0.92581 (17) | 0.13786 (8) | 0.0129 (3) | |
C8 | 0.5093 (2) | 0.78171 (16) | 0.07486 (8) | 0.0120 (3) | |
C9 | 0.9839 (2) | 0.71983 (16) | −0.07846 (8) | 0.0120 (3) | |
C10 | 1.0630 (3) | 0.57244 (17) | −0.13972 (8) | 0.0137 (3) | |
C11 | 1.0445 (2) | 0.61346 (16) | −0.23584 (8) | 0.0127 (3) | |
C12 | 1.2278 (3) | 0.70965 (18) | −0.27062 (9) | 0.0162 (3) | |
C13 | 1.2100 (3) | 0.74792 (18) | −0.35846 (9) | 0.0186 (3) | |
C14 | 1.0109 (3) | 0.68811 (19) | −0.41296 (9) | 0.0200 (3) | |
C15 | 0.8286 (3) | 0.59203 (19) | −0.37894 (9) | 0.0196 (3) | |
C16 | 0.8446 (3) | 0.55437 (17) | −0.29055 (9) | 0.0161 (3) | |
H1N1 | 0.787 (3) | 0.915 (2) | 0.0321 (11) | 0.023 (5)* | |
H1N2 | 0.705 (3) | 0.593 (2) | −0.0350 (11) | 0.017 (4)* | |
H1A | 0.148 (3) | 1.007 (2) | 0.2720 (11) | 0.022 (4)* | |
H2A | 0.175 (3) | 0.951 (2) | 0.4219 (10) | 0.017 (4)* | |
H3A | 0.519 (4) | 0.786 (2) | 0.4710 (13) | 0.031 (5)* | |
H4A | 0.809 (3) | 0.686 (2) | 0.3727 (11) | 0.021 (4)* | |
H5A | 0.775 (3) | 0.747 (2) | 0.2245 (11) | 0.018 (4)* | |
H7A | 0.529 (3) | 1.028 (2) | 0.1304 (10) | 0.018 (4)* | |
H7B | 0.259 (4) | 0.953 (2) | 0.1223 (12) | 0.027 (5)* | |
H10A | 0.967 (3) | 0.471 (2) | −0.1318 (10) | 0.016 (4)* | |
H10B | 1.240 (3) | 0.554 (2) | −0.1200 (11) | 0.021 (4)* | |
H12A | 1.373 (3) | 0.757 (2) | −0.2322 (11) | 0.022 (4)* | |
H13A | 1.339 (3) | 0.814 (2) | −0.3815 (12) | 0.029 (5)* | |
H14A | 1.002 (3) | 0.713 (2) | −0.4733 (12) | 0.028 (5)* | |
H16A | 0.720 (3) | 0.489 (2) | −0.2662 (12) | 0.029 (5)* | |
H15A | 0.692 (3) | 0.549 (2) | −0.4190 (11) | 0.017 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0172 (5) | 0.0123 (5) | 0.0198 (5) | −0.0052 (4) | 0.0047 (4) | −0.0010 (4) |
O2 | 0.0172 (5) | 0.0119 (5) | 0.0206 (5) | −0.0033 (4) | 0.0051 (4) | −0.0013 (4) |
N1 | 0.0151 (6) | 0.0101 (5) | 0.0141 (5) | −0.0019 (4) | 0.0042 (4) | −0.0016 (4) |
N2 | 0.0156 (6) | 0.0100 (5) | 0.0150 (5) | −0.0023 (4) | 0.0052 (4) | −0.0021 (4) |
C1 | 0.0137 (6) | 0.0143 (6) | 0.0184 (6) | −0.0001 (5) | 0.0029 (5) | 0.0002 (5) |
C2 | 0.0195 (7) | 0.0175 (7) | 0.0185 (7) | −0.0024 (5) | 0.0059 (5) | −0.0006 (5) |
C3 | 0.0235 (8) | 0.0176 (7) | 0.0143 (6) | −0.0031 (6) | 0.0014 (5) | 0.0021 (5) |
C4 | 0.0170 (7) | 0.0173 (7) | 0.0191 (7) | 0.0005 (5) | −0.0028 (5) | 0.0005 (5) |
C5 | 0.0142 (6) | 0.0146 (6) | 0.0169 (6) | 0.0002 (5) | 0.0022 (5) | −0.0011 (5) |
C6 | 0.0128 (6) | 0.0107 (6) | 0.0143 (6) | −0.0038 (5) | 0.0017 (5) | −0.0007 (5) |
C7 | 0.0139 (6) | 0.0106 (6) | 0.0143 (6) | 0.0000 (5) | 0.0028 (5) | −0.0003 (5) |
C8 | 0.0124 (6) | 0.0114 (6) | 0.0121 (6) | −0.0005 (5) | −0.0006 (5) | 0.0013 (4) |
C9 | 0.0134 (6) | 0.0112 (6) | 0.0115 (6) | −0.0001 (5) | 0.0012 (5) | 0.0013 (4) |
C10 | 0.0156 (7) | 0.0107 (6) | 0.0149 (6) | −0.0003 (5) | 0.0039 (5) | 0.0007 (5) |
C11 | 0.0132 (6) | 0.0090 (6) | 0.0161 (6) | 0.0016 (5) | 0.0037 (5) | −0.0008 (5) |
C12 | 0.0148 (7) | 0.0155 (6) | 0.0179 (6) | −0.0020 (5) | 0.0026 (5) | −0.0013 (5) |
C13 | 0.0211 (7) | 0.0169 (7) | 0.0182 (7) | −0.0019 (5) | 0.0060 (5) | 0.0009 (5) |
C14 | 0.0254 (8) | 0.0191 (7) | 0.0155 (6) | 0.0040 (6) | 0.0016 (6) | 0.0016 (5) |
C15 | 0.0185 (7) | 0.0185 (7) | 0.0210 (7) | 0.0010 (6) | −0.0043 (6) | −0.0005 (5) |
C16 | 0.0131 (6) | 0.0140 (6) | 0.0212 (7) | −0.0018 (5) | 0.0020 (5) | 0.0012 (5) |
O1—C8 | 1.2355 (16) | C7—C8 | 1.5089 (18) |
O2—C9 | 1.2332 (16) | C7—H7A | 0.975 (18) |
N1—C8 | 1.3426 (16) | C7—H7B | 1.002 (19) |
N1—N2 | 1.3922 (14) | C9—C10 | 1.5183 (18) |
N1—H1N1 | 0.908 (19) | C10—C11 | 1.5172 (18) |
N2—C9 | 1.3443 (16) | C10—H10A | 0.972 (17) |
N2—H1N2 | 0.869 (18) | C10—H10B | 1.013 (18) |
C1—C2 | 1.3888 (19) | C11—C16 | 1.3934 (19) |
C1—C6 | 1.3977 (18) | C11—C12 | 1.3951 (18) |
C1—H1A | 0.950 (18) | C12—C13 | 1.3884 (19) |
C2—C3 | 1.390 (2) | C12—H12A | 1.009 (18) |
C2—H2A | 1.000 (16) | C13—C14 | 1.390 (2) |
C3—C4 | 1.388 (2) | C13—H13A | 0.963 (19) |
C3—H3A | 0.942 (19) | C14—C15 | 1.385 (2) |
C4—C5 | 1.3899 (19) | C14—H14A | 0.949 (18) |
C4—H4A | 0.977 (17) | C15—C16 | 1.3948 (19) |
C5—C6 | 1.3960 (18) | C15—H15A | 0.980 (17) |
C5—H5A | 0.986 (17) | C16—H16A | 0.954 (19) |
C6—C7 | 1.5167 (18) | ||
C8—N1—N2 | 118.83 (11) | O1—C8—N1 | 121.88 (12) |
C8—N1—H1N1 | 123.8 (11) | O1—C8—C7 | 122.94 (12) |
N2—N1—H1N1 | 117.2 (11) | N1—C8—C7 | 115.18 (11) |
C9—N2—N1 | 118.90 (11) | O2—C9—N2 | 122.08 (12) |
C9—N2—H1N2 | 125.2 (11) | O2—C9—C10 | 123.08 (12) |
N1—N2—H1N2 | 115.9 (11) | N2—C9—C10 | 114.84 (11) |
C2—C1—C6 | 120.35 (13) | C11—C10—C9 | 111.62 (11) |
C2—C1—H1A | 120.4 (10) | C11—C10—H10A | 110.1 (9) |
C6—C1—H1A | 119.2 (10) | C9—C10—H10A | 111.1 (10) |
C1—C2—C3 | 120.42 (13) | C11—C10—H10B | 110.7 (10) |
C1—C2—H2A | 118.5 (9) | C9—C10—H10B | 104.3 (10) |
C3—C2—H2A | 121.0 (9) | H10A—C10—H10B | 108.8 (14) |
C4—C3—C2 | 119.67 (13) | C16—C11—C12 | 119.24 (12) |
C4—C3—H3A | 117.1 (12) | C16—C11—C10 | 120.29 (12) |
C2—C3—H3A | 123.2 (12) | C12—C11—C10 | 120.47 (12) |
C3—C4—C5 | 120.00 (13) | C13—C12—C11 | 120.42 (14) |
C3—C4—H4A | 121.6 (10) | C13—C12—H12A | 118.5 (10) |
C5—C4—H4A | 118.4 (10) | C11—C12—H12A | 121.0 (10) |
C4—C5—C6 | 120.81 (12) | C12—C13—C14 | 120.18 (13) |
C4—C5—H5A | 119.2 (9) | C12—C13—H13A | 119.3 (11) |
C6—C5—H5A | 120.0 (9) | C14—C13—H13A | 120.5 (11) |
C5—C6—C1 | 118.74 (12) | C15—C14—C13 | 119.70 (13) |
C5—C6—C7 | 121.05 (11) | C15—C14—H14A | 120.6 (12) |
C1—C6—C7 | 120.17 (12) | C13—C14—H14A | 119.7 (12) |
C8—C7—C6 | 112.43 (11) | C14—C15—C16 | 120.35 (14) |
C8—C7—H7A | 111.1 (10) | C14—C15—H15A | 118.1 (10) |
C6—C7—H7A | 110.0 (9) | C16—C15—H15A | 121.5 (10) |
C8—C7—H7B | 108.1 (11) | C11—C16—C15 | 120.10 (13) |
C6—C7—H7B | 108.9 (10) | C11—C16—H16A | 118.7 (11) |
H7A—C7—H7B | 105.9 (14) | C15—C16—H16A | 121.2 (11) |
C8—N1—N2—C9 | 179.72 (11) | N1—N2—C9—O2 | −2.93 (19) |
C6—C1—C2—C3 | −0.6 (2) | N1—N2—C9—C10 | 177.53 (11) |
C1—C2—C3—C4 | 0.2 (2) | O2—C9—C10—C11 | −61.91 (17) |
C2—C3—C4—C5 | 0.6 (2) | N2—C9—C10—C11 | 117.63 (13) |
C3—C4—C5—C6 | −1.1 (2) | C9—C10—C11—C16 | −100.39 (15) |
C4—C5—C6—C1 | 0.6 (2) | C9—C10—C11—C12 | 80.05 (15) |
C4—C5—C6—C7 | 178.53 (13) | C16—C11—C12—C13 | 0.8 (2) |
C2—C1—C6—C5 | 0.2 (2) | C10—C11—C12—C13 | −179.64 (12) |
C2—C1—C6—C7 | −177.69 (13) | C11—C12—C13—C14 | −1.1 (2) |
C5—C6—C7—C8 | 39.28 (18) | C12—C13—C14—C15 | 0.9 (2) |
C1—C6—C7—C8 | −142.87 (13) | C13—C14—C15—C16 | −0.3 (2) |
N2—N1—C8—O1 | 1.69 (19) | C12—C11—C16—C15 | −0.3 (2) |
N2—N1—C8—C7 | −179.17 (11) | C10—C11—C16—C15 | −179.84 (12) |
C6—C7—C8—O1 | 62.54 (17) | C14—C15—C16—C11 | 0.1 (2) |
C6—C7—C8—N1 | −116.59 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.867 (16) | 1.970 (16) | 2.8076 (15) | 162.4 (16) |
C10—H10A···O1i | 0.971 (16) | 2.465 (16) | 3.3103 (18) | 145.3 (13) |
N1—H1N1···O2ii | 0.907 (16) | 1.948 (16) | 2.8283 (15) | 163.2 (15) |
C7—H7A···O2ii | 0.973 (16) | 2.479 (16) | 3.3209 (18) | 144.8 (13) |
C7—H7B···O2iii | 1.00 (2) | 2.56 (2) | 3.4929 (19) | 155.2 (13) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+2, −z; (iii) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C16H16N2O2 |
Mr | 268.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 5.4531 (6), 7.9283 (9), 15.1758 (17) |
α, β, γ (°) | 94.271 (2), 92.613 (2), 90.830 (2) |
V (Å3) | 653.50 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.35 × 0.14 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART APEXII DUO CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.968, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12991, 3458, 2428 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.682 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.134, 1.04 |
No. of reflections | 3458 |
No. of parameters | 245 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.38, −0.29 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.867 (16) | 1.970 (16) | 2.8076 (15) | 162.4 (16) |
C10—H10A···O1i | 0.971 (16) | 2.465 (16) | 3.3103 (18) | 145.3 (13) |
N1—H1N1···O2ii | 0.907 (16) | 1.948 (16) | 2.8283 (15) | 163.2 (15) |
C7—H7A···O2ii | 0.973 (16) | 2.479 (16) | 3.3209 (18) | 144.8 (13) |
C7—H7B···O2iii | 1.00 (2) | 2.56 (2) | 3.4929 (19) | 155.2 (13) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+2, −z; (iii) −x+1, −y+2, −z. |
Acknowledgements
The authors thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160) and the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University.
References
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Hydrazine derivatives are widely used in the pharmaceutical applications and also as precursors in organic synthesis (Bredihhin & Mäeorg, 2008). Several hydrazine derivatives were shown to be effective for treatment of tuberculosis, Parkinson's disease and hypertension (Ragnarsson, 2001). Moreover, some hydrazines possess neuroprotective activity and are used as antidepressant drugs (Ling et al., 2001).
In the title compound, Fig. 1, the N'-acetylacetohydrazide moiety (O1/O2/N1/N2/C7-C10) is approximately planar (r.m.s. deviation = 0.018 Å for the 8 non-H atoms) and makes dihedral angles of 81.92 (6) and 65.19 (6)° with the two terminal benzene rings (C1-C6 and C11-C16), respectively. The two benzene rings form a dihedral angle of 62.60 (7)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges.
In the crystal (Fig.2), molecules are linked into planes parallel to the (001) via intermolecular N1–H1N1···O2, C7–H7A···O2 and C7–H7B···O2 trifurcated acceptor bonds (Table 1) and N2–H1N2···O1 and C10–H10A···O1 bifurcated acceptor bonds (Table 1), generating R21(6) ring motifs (Bernstein et al., 1995).