4-Phenyl­butan-2-one semi­carbazone

Degen, A.; Rühl, S.; Bolte, M.

doi:10.1107/S0108270100003802

4-Phenylbutan-2-one semicarbazone

The title compound, C₁₁H₁₅N₃O, crystallizes with two molecules in the asymmetric unit, which are held together by an extended network of hydrogen bonds. It is remarkable that only five of the six theoretically possible hydrogen bonds are formed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003802/qa0243sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003802/qa0243Isup2.hkl Contains datablock I

CCDC reference: 144719

Comment top

The semicarbazone moiety is found very often in molecules complexing different metal atoms (Palenik et al., 1976; Palenik & Wester, 1978). Since the complexing atoms are the carbonyl O atom and the imine N atom, the conformation of the O═C—N—N fragment is cis. However, the free semicarbazone moiety prefers the trans conformation of the O═ C—N—N fragment; of 67 fragments retrieved from the Cambridge Structural Database (Version 5.18 of October 1999; Allen & Kennard, 1993), only seven display a cis conformation of the fragment in question. Bond lengths and angles do not show remarkable differences between complexing and non-complexing semicarbazone moieties. The phenylethyl moiety of one of the two molecules in the asymmetric unit is disordered. The reason for this disorder is differences in the torsion angles about the bonds C1—C11, C1A—C11A and C1B—C11B, and about C2—C3, C2A—C3 and C2B—C3. The torsion angle about the CH₂—CH₂ bond is trans in all three conformations.

A remarkable feature of the title compound, (I), is that only five of the six possible hydrogen bonds are formed. While the two carbonyl O atoms act as an acceptor for two hydrogen bonds each, only one of the imine N atoms is involved in a hydrogen bond. The closest H atom to N4A (N···H 2.774 Å) is H4Cⁱ [symmetry code: (i) x, y - 1, z], one of the methyl H atoms of C4.

Experimental top

To a stirred solution of 150 ml warm sodium ethylate (500 mmol sodium) and 63.16 ml (500 mmol) acetoacetic ester 60 ml freshly distilled (0.52 mmol), benzyl chloride was added dropwise. The mixture was refluxed for 16 h. For working up, the ethanol was removed by distillation. The solid residue was dissolved in 100 ml water containing 50 g ice. The solution was extracted three times with diethyl ether and the organic phase was dried with sodium sulfate. After removing the solvent, the crude 2-benzyl acetoacetic ester was purified by fractional distillation. In the second reaction step, 22.0 g (100 mmol) of 2-benzyl acetoacetic ester and 11.22 g (200 mmol) potassium hydroxide in 100 ml absolute ethanol were boiled to reflux for 14 h. The mixture was hydrolyzed in 300 ml iced water containing 5 ml concentrated sulfuric acid. The solution was extracted four times with diethyl ether. The organic phase was washed with water and dried over sodium sulfate. 4-Phenyl-2-butanone was purified by fractional distillation under vacuum. In the last step, 5 g (45 mmol) semicarbazide hydrochloride and 10 g (122 mmol) sodium acetate in 30 ml water was added to 2 g (13 mmol) 4-phenyl-2-butanone in 30 ml e thanol. The crude product was collected by filtration. Recrystallization from acetone yielded crystals suitable for X-ray diffraction.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

4-Phenylbutan-2-one semicarbazone top

Crystal data top

C₁₁H₁₅N₃O	F(000) = 880
M_r = 205.26	D_x = 1.206 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 14.059 (1) Å	Cell parameters from 508 reflections
b = 7.1282 (9) Å	θ = 1–25°
c = 22.621 (2) Å	µ = 0.08 mm⁻¹
β = 94.148 (1)°	T = 173 K
V = 2261.0 (4) Å³	Plate, colourless
Z = 8	0.72 × 0.58 × 0.12 mm

Data collection top

Siemens CCD three-circle diffractometer	5099 independent reflections
Radiation source: fine-focus sealed tube	4035 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −17→18
T_min = 0.944, T_max = 0.990	k = −8→9
33568 measured reflections	l = −29→28

Refinement top

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0392P)² + 0.8063P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
5099 reflections	Δρ_max = 0.24 e Å⁻³
371 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0044 (6)

Crystal data top

C₁₁H₁₅N₃O	V = 2261.0 (4) Å³
M_r = 205.26	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.059 (1) Å	µ = 0.08 mm⁻¹
b = 7.1282 (9) Å	T = 173 K
c = 22.621 (2) Å	0.72 × 0.58 × 0.12 mm
β = 94.148 (1)°

Data collection top

Siemens CCD three-circle diffractometer	5099 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	4035 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.990	R_int = 0.038
33568 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.24 e Å⁻³
5099 reflections	Δρ_min = −0.20 e Å⁻³
371 parameters

Special details top

Experimental. The data collection nominally covered a sphere of reciprocal space, by a combination of seven sets of exposures; each set had a different ϕ angle for the crystal and each exposure covered 0.3° in ω. The crystal-to-detector distance was 5.5 cm. Crystal decay was monitored by repeating the initial frames at the end of data collection and analyzing the duplicate reflections.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.49261 (10)	1.78779 (19)	0.68999 (6)	0.0310 (3)
H1A	0.5208	1.7813	0.6512	0.037*
H1B	0.4242	1.8195	0.6826	0.037*
C2	0.50184 (10)	1.59548 (18)	0.72033 (6)	0.0292 (3)
H2A	0.5702	1.5674	0.7298	0.035*
H2B	0.4704	1.6001	0.7581	0.035*
C3	0.45801 (9)	1.44085 (18)	0.68233 (6)	0.0261 (3)
C4	0.50603 (10)	1.3850 (2)	0.62788 (6)	0.0340 (3)
H4A	0.5231	1.2518	0.6304	0.051*
H4B	0.5638	1.4603	0.6250	0.051*
H4C	0.4625	1.4064	0.5927	0.051*
N4	0.38119 (8)	1.36727 (15)	0.69889 (5)	0.0264 (2)
N5	0.34025 (8)	1.22161 (15)	0.66505 (5)	0.0271 (2)
H5	0.3672 (11)	1.175 (2)	0.6348 (7)	0.038 (4)*
C6	0.27185 (9)	1.11428 (18)	0.68860 (6)	0.0270 (3)
N6	0.23999 (10)	1.16964 (18)	0.74029 (6)	0.0349 (3)
H6A	0.2672 (11)	1.261 (3)	0.7601 (7)	0.039 (4)*
H6B	0.2002 (11)	1.095 (2)	0.7566 (7)	0.038 (4)*
O6	0.24047 (7)	0.97234 (13)	0.66192 (4)	0.0338 (2)
C11	0.54171 (9)	1.94011 (18)	0.72695 (6)	0.0279 (3)
C12	0.49615 (10)	2.0273 (2)	0.77192 (6)	0.0331 (3)
H12	0.4331	1.9907	0.7794	0.040*
C13	0.54131 (11)	2.1674 (2)	0.80621 (7)	0.0375 (3)
H13	0.5089	2.2266	0.8366	0.045*
C14	0.63308 (11)	2.2208 (2)	0.79624 (7)	0.0397 (4)
H14	0.6641	2.3161	0.8198	0.048*
C15	0.67973 (11)	2.1350 (2)	0.75180 (8)	0.0436 (4)
H15	0.7429	2.1714	0.7447	0.052*
C16	0.63403 (10)	1.9951 (2)	0.71748 (7)	0.0371 (3)
H16	0.6666	1.9364	0.6871	0.045*
C1A	0.1511 (2)	0.2962 (4)	0.47715 (12)	0.0457 (9)	0.604 (4)
H1A1	0.0862	0.3359	0.4861	0.055*	0.604 (4)
H1A2	0.1745	0.3865	0.4483	0.055*	0.604 (4)
C2A	0.2165 (3)	0.3053 (8)	0.5342 (3)	0.0326 (9)	0.604 (4)
H2A1	0.2805	0.2570	0.5266	0.039*	0.604 (4)
H2A2	0.1903	0.2251	0.5649	0.039*	0.604 (4)
C3A	0.22523 (11)	0.5084 (2)	0.55692 (6)	0.0370 (3)
C4A	0.15498 (14)	0.5903 (3)	0.59537 (12)	0.0776 (7)
H4A1	0.1812	0.5884	0.6367	0.116*
H4A2	0.0960	0.5166	0.5916	0.116*
H4A3	0.1412	0.7201	0.5832	0.116*
N4A	0.30158 (9)	0.58824 (17)	0.54300 (5)	0.0365 (3)
N5A	0.32267 (8)	0.76599 (16)	0.56475 (5)	0.0290 (3)
H5A	0.2895 (11)	0.826 (2)	0.5901 (7)	0.039 (4)*
C6A	0.39832 (9)	0.85838 (19)	0.54444 (5)	0.0269 (3)
N6A	0.45087 (10)	0.76461 (19)	0.50703 (6)	0.0399 (3)
H6D	0.4941 (13)	0.831 (3)	0.4868 (8)	0.050 (5)*
H6C	0.4270 (13)	0.656 (3)	0.4946 (8)	0.055 (5)*
O6A	0.41757 (7)	1.02098 (13)	0.56136 (4)	0.0322 (2)
C11A	0.1450 (5)	0.1044 (6)	0.44885 (15)	0.0345 (9)	0.604 (4)
C12A	0.2267 (5)	0.0096 (9)	0.4349 (3)	0.0420 (14)	0.604 (4)
H12A	0.2869	0.0630	0.4470	0.050*	0.604 (4)
C13A	0.2247 (9)	−0.165 (3)	0.4034 (9)	0.056 (4)	0.604 (4)
H13A	0.2822	−0.2252	0.3944	0.067*	0.604 (4)
C14A	0.1350 (9)	−0.244 (2)	0.3859 (6)	0.0445 (17)	0.604 (4)
H14A	0.1303	−0.3583	0.3640	0.053*	0.604 (4)
C15A	0.0519 (8)	−0.1488 (15)	0.4021 (4)	0.0520 (16)	0.604 (4)
H15A	−0.0091	−0.2013	0.3916	0.062*	0.604 (4)
C16A	0.0582 (4)	0.0190 (8)	0.4328 (2)	0.0428 (9)	0.604 (4)
H16A	0.0012	0.0779	0.4433	0.051*	0.604 (4)
C1B	0.2341 (3)	0.2781 (5)	0.47455 (17)	0.0380 (12)	0.396 (4)
H1B1	0.3025	0.2592	0.4868	0.046*	0.396 (4)
H1B2	0.2295	0.3795	0.4446	0.046*	0.396 (4)
C2B	0.1830 (5)	0.3385 (14)	0.5276 (4)	0.047 (2)	0.396 (4)
H2B1	0.1153	0.3639	0.5150	0.056*	0.396 (4)
H2B2	0.1846	0.2345	0.5567	0.056*	0.396 (4)
C11B	0.1935 (7)	0.0967 (10)	0.4463 (2)	0.0331 (13)	0.396 (4)
C12B	0.2560 (7)	−0.0308 (16)	0.4243 (5)	0.0412 (18)	0.396 (4)
H12B	0.3230	−0.0113	0.4274	0.049*	0.396 (4)
C13B	0.2161 (17)	−0.183 (4)	0.3985 (15)	0.064 (6)	0.396 (4)
H13B	0.2572	−0.2745	0.3833	0.076*	0.396 (4)
C14B	0.123 (2)	−0.216 (4)	0.3928 (10)	0.070 (6)	0.396 (4)
H14B	0.1001	−0.3287	0.3742	0.084*	0.396 (4)
C15B	0.0627 (14)	−0.100 (2)	0.4118 (7)	0.059 (4)	0.396 (4)
H15B	−0.0038	−0.1246	0.4068	0.071*	0.396 (4)
C16B	0.0966 (7)	0.0624 (10)	0.4400 (3)	0.0428 (17)	0.396 (4)
H16B	0.0533	0.1498	0.4549	0.051*	0.396 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0354 (7)	0.0228 (7)	0.0342 (7)	−0.0017 (6)	−0.0024 (6)	0.0002 (6)
C2	0.0333 (7)	0.0227 (7)	0.0315 (7)	−0.0016 (5)	0.0016 (5)	−0.0002 (5)
C3	0.0288 (6)	0.0193 (6)	0.0306 (7)	0.0011 (5)	0.0051 (5)	0.0013 (5)
C4	0.0338 (7)	0.0276 (7)	0.0425 (8)	−0.0054 (6)	0.0154 (6)	−0.0060 (6)
N4	0.0333 (6)	0.0187 (5)	0.0277 (5)	−0.0019 (5)	0.0058 (4)	−0.0014 (4)
N5	0.0330 (6)	0.0222 (6)	0.0276 (6)	−0.0046 (5)	0.0111 (5)	−0.0044 (5)
C6	0.0291 (6)	0.0198 (6)	0.0331 (7)	0.0009 (5)	0.0087 (5)	0.0007 (5)
N6	0.0438 (7)	0.0248 (6)	0.0387 (7)	−0.0087 (6)	0.0217 (6)	−0.0061 (5)
O6	0.0391 (5)	0.0260 (5)	0.0379 (5)	−0.0089 (4)	0.0141 (4)	−0.0059 (4)
C11	0.0313 (7)	0.0188 (6)	0.0329 (7)	0.0004 (5)	−0.0029 (5)	0.0041 (5)
C12	0.0318 (7)	0.0288 (7)	0.0387 (8)	−0.0020 (6)	0.0032 (6)	0.0007 (6)
C13	0.0466 (8)	0.0295 (7)	0.0365 (8)	−0.0007 (7)	0.0037 (6)	−0.0043 (6)
C14	0.0457 (9)	0.0291 (8)	0.0429 (8)	−0.0073 (7)	−0.0069 (7)	−0.0029 (6)
C15	0.0317 (7)	0.0409 (9)	0.0576 (10)	−0.0086 (7)	0.0004 (7)	−0.0013 (8)
C16	0.0343 (7)	0.0317 (8)	0.0455 (8)	0.0008 (6)	0.0046 (6)	−0.0034 (6)
C1A	0.060 (2)	0.0354 (15)	0.0399 (15)	0.0067 (13)	−0.0091 (13)	−0.0043 (12)
C2A	0.036 (2)	0.0274 (19)	0.0337 (15)	−0.0072 (19)	−0.0009 (19)	0.0008 (12)
C3A	0.0414 (8)	0.0360 (8)	0.0342 (7)	−0.0122 (7)	0.0061 (6)	−0.0053 (6)
C4A	0.0509 (11)	0.0646 (13)	0.1226 (19)	−0.0263 (10)	0.0434 (12)	−0.0372 (13)
N4A	0.0475 (7)	0.0280 (6)	0.0355 (6)	−0.0108 (5)	0.0124 (5)	−0.0083 (5)
N5A	0.0333 (6)	0.0254 (6)	0.0295 (6)	−0.0058 (5)	0.0097 (5)	−0.0067 (5)
C6A	0.0309 (7)	0.0265 (7)	0.0237 (6)	−0.0016 (5)	0.0045 (5)	0.0005 (5)
N6A	0.0481 (8)	0.0298 (7)	0.0449 (7)	−0.0099 (6)	0.0254 (6)	−0.0078 (6)
O6A	0.0396 (5)	0.0267 (5)	0.0316 (5)	−0.0078 (4)	0.0117 (4)	−0.0051 (4)
C11A	0.041 (3)	0.032 (2)	0.0296 (15)	0.000 (3)	−0.002 (2)	−0.0020 (13)
C12A	0.044 (4)	0.041 (4)	0.040 (3)	0.004 (2)	−0.006 (2)	−0.003 (2)
C13A	0.055 (4)	0.061 (11)	0.051 (4)	0.011 (4)	−0.003 (3)	0.005 (5)
C14A	0.072 (4)	0.023 (4)	0.037 (3)	−0.006 (3)	−0.002 (3)	−0.012 (3)
C15A	0.064 (4)	0.045 (5)	0.046 (3)	−0.027 (3)	−0.001 (3)	−0.004 (3)
C16A	0.049 (3)	0.040 (3)	0.0395 (19)	−0.018 (2)	0.001 (2)	0.0011 (19)
C1B	0.043 (3)	0.032 (2)	0.040 (2)	−0.0079 (17)	0.0069 (16)	−0.0057 (16)
C2B	0.044 (4)	0.048 (5)	0.051 (4)	−0.015 (4)	0.010 (4)	−0.011 (3)
C11B	0.040 (4)	0.030 (3)	0.030 (2)	0.003 (4)	0.005 (3)	0.000 (2)
C12B	0.051 (5)	0.033 (4)	0.039 (4)	0.002 (4)	−0.004 (3)	−0.004 (3)
C13B	0.105 (13)	0.028 (6)	0.056 (8)	−0.001 (6)	−0.009 (7)	0.000 (5)
C14B	0.133 (15)	0.026 (7)	0.050 (6)	−0.013 (7)	0.009 (6)	−0.023 (4)
C15B	0.069 (5)	0.051 (9)	0.056 (6)	−0.042 (6)	−0.009 (4)	−0.013 (5)
C16B	0.043 (5)	0.034 (4)	0.051 (4)	−0.016 (4)	0.003 (4)	−0.014 (3)

Geometric parameters (Å, º) top

C1—C11	1.5069 (18)	C3A—C2B	1.484 (10)
C1—C2	1.5343 (18)	C4A—H4A1	0.9800
C1—H1A	0.9900	C4A—H4A2	0.9800
C1—H1B	0.9900	C4A—H4A3	0.9800
C2—C3	1.5023 (18)	N4A—N5A	1.3836 (16)
C2—H2A	0.9900	N5A—C6A	1.3589 (17)
C2—H2B	0.9900	N5A—H5A	0.877 (17)
C3—N4	1.2807 (16)	C6A—O6A	1.2442 (16)
C3—C4	1.5004 (18)	C6A—N6A	1.3413 (17)
C4—H4A	0.9800	N6A—H6D	0.917 (19)
C4—H4B	0.9800	N6A—H6C	0.88 (2)
C4—H4C	0.9800	C11A—C16A	1.388 (5)
N4—N5	1.3899 (15)	C11A—C12A	1.388 (5)
N5—C6	1.3667 (16)	C12A—C13A	1.43 (2)
N5—H5	0.872 (17)	C12A—H12A	0.9500
C6—O6	1.2426 (16)	C13A—C14A	1.41 (2)
C6—N6	1.3414 (17)	C13A—H13A	0.9500
N6—H6A	0.861 (18)	C14A—C15A	1.42 (2)
N6—H6B	0.874 (17)	C14A—H14A	0.9500
C11—C16	1.387 (2)	C15A—C16A	1.383 (8)
C11—C12	1.388 (2)	C15A—H15A	0.9500
C12—C13	1.389 (2)	C16A—H16A	0.9500
C12—H12	0.9500	C1B—C2B	1.506 (11)
C13—C14	1.379 (2)	C1B—C11B	1.535 (8)
C13—H13	0.9500	C1B—H1B1	0.9900
C14—C15	1.382 (2)	C1B—H1B2	0.9900
C14—H14	0.9500	C2B—H2B1	0.9900
C15—C16	1.392 (2)	C2B—H2B2	0.9900
C15—H15	0.9500	C11B—C12B	1.381 (7)
C16—H16	0.9500	C11B—C16B	1.381 (8)
C1A—C11A	1.509 (5)	C12B—C13B	1.34 (3)
C1A—C2A	1.532 (5)	C12B—H12B	0.9500
C1A—H1A1	0.9900	C13B—C14B	1.33 (3)
C1A—H1A2	0.9900	C13B—H13B	0.9500
C2A—C3A	1.538 (6)	C14B—C15B	1.28 (3)
C2A—H2A1	0.9900	C14B—H14B	0.9500
C2A—H2A2	0.9900	C15B—C16B	1.391 (9)
C3A—N4A	1.2744 (18)	C15B—H15B	0.9500
C3A—C4A	1.482 (2)	C16B—H16B	0.9500

C11—C1—C2	112.03 (11)	C2B—C3A—C2A	20.5 (3)
C11—C1—H1A	109.2	C3A—C4A—H4A1	109.5
C2—C1—H1A	109.2	C3A—C4A—H4A2	109.5
C11—C1—H1B	109.2	H4A1—C4A—H4A2	109.5
C2—C1—H1B	109.2	C3A—C4A—H4A3	109.5
H1A—C1—H1B	107.9	H4A1—C4A—H4A3	109.5
C3—C2—C1	112.44 (11)	H4A2—C4A—H4A3	109.5
C3—C2—H2A	109.1	C3A—N4A—N5A	118.92 (12)
C1—C2—H2A	109.1	C6A—N5A—N4A	118.45 (11)
C3—C2—H2B	109.1	C6A—N5A—H5A	116.9 (11)
C1—C2—H2B	109.1	N4A—N5A—H5A	124.6 (11)
H2A—C2—H2B	107.8	O6A—C6A—N6A	122.74 (12)
N4—C3—C4	124.78 (12)	O6A—C6A—N5A	120.37 (12)
N4—C3—C2	116.91 (12)	N6A—C6A—N5A	116.88 (12)
C4—C3—C2	118.30 (11)	C6A—N6A—H6D	118.3 (11)
C3—C4—H4A	109.5	C6A—N6A—H6C	115.2 (12)
C3—C4—H4B	109.5	H6D—N6A—H6C	122.8 (16)
H4A—C4—H4B	109.5	C16A—C11A—C12A	116.9 (6)
C3—C4—H4C	109.5	C16A—C11A—C1A	122.0 (6)
H4A—C4—H4C	109.5	C12A—C11A—C1A	121.0 (6)
H4B—C4—H4C	109.5	C11A—C12A—C13A	123.3 (7)
C3—N4—N5	117.98 (11)	C11A—C12A—H12A	118.3
C6—N5—N4	118.59 (11)	C13A—C12A—H12A	118.3
C6—N5—H5	116.8 (11)	C14A—C13A—C12A	118.2 (11)
N4—N5—H5	122.0 (11)	C14A—C13A—H13A	120.9
O6—C6—N6	122.26 (12)	C12A—C13A—H13A	120.9
O6—C6—N5	120.10 (12)	C13A—C14A—C15A	117.9 (12)
N6—C6—N5	117.63 (12)	C13A—C14A—H14A	121.0
C6—N6—H6A	120.7 (11)	C15A—C14A—H14A	121.0
C6—N6—H6B	116.8 (11)	C16A—C15A—C14A	121.3 (9)
H6A—N6—H6B	121.1 (15)	C16A—C15A—H15A	119.4
C16—C11—C12	118.24 (13)	C14A—C15A—H15A	119.4
C16—C11—C1	120.94 (13)	C15A—C16A—C11A	122.3 (8)
C12—C11—C1	120.82 (12)	C15A—C16A—H16A	118.8
C11—C12—C13	120.98 (13)	C11A—C16A—H16A	118.8
C11—C12—H12	119.5	C2B—C1B—C11B	112.9 (5)
C13—C12—H12	119.5	C2B—C1B—H1B1	109.0
C14—C13—C12	120.14 (14)	C11B—C1B—H1B1	109.0
C14—C13—H13	119.9	C2B—C1B—H1B2	109.0
C12—C13—H13	119.9	C11B—C1B—H1B2	109.0
C13—C14—C15	119.71 (14)	H1B1—C1B—H1B2	107.8
C13—C14—H14	120.1	C3A—C2B—C1B	113.0 (6)
C15—C14—H14	120.1	C3A—C2B—H2B1	109.0
C14—C15—C16	119.90 (14)	C1B—C2B—H2B1	109.0
C14—C15—H15	120.0	C3A—C2B—H2B2	109.0
C16—C15—H15	120.0	C1B—C2B—H2B2	109.0
C11—C16—C15	121.04 (14)	H2B1—C2B—H2B2	107.8
C11—C16—H16	119.5	C12B—C11B—C16B	119.7 (8)
C15—C16—H16	119.5	C12B—C11B—C1B	118.5 (9)
C11A—C1A—C2A	114.1 (3)	C16B—C11B—C1B	121.7 (8)
C11A—C1A—H1A1	108.7	C13B—C12B—C11B	115.7 (13)
C2A—C1A—H1A1	108.7	C13B—C12B—H12B	122.1
C11A—C1A—H1A2	108.7	C11B—C12B—H12B	122.1
C2A—C1A—H1A2	108.7	C14B—C13B—C12B	124 (2)
H1A1—C1A—H1A2	107.6	C14B—C13B—H13B	117.8
C1A—C2A—C3A	110.5 (3)	C12B—C13B—H13B	117.8
C1A—C2A—H2A1	109.6	C15B—C14B—C13B	122 (2)
C3A—C2A—H2A1	109.6	C15B—C14B—H14B	119.2
C1A—C2A—H2A2	109.6	C13B—C14B—H14B	119.2
C3A—C2A—H2A2	109.6	C14B—C15B—C16B	118.7 (17)
H2A1—C2A—H2A2	108.1	C14B—C15B—H15B	120.6
N4A—C3A—C4A	125.32 (14)	C16B—C15B—H15B	120.6
N4A—C3A—C2B	124.8 (4)	C11B—C16B—C15B	119.8 (10)
C4A—C3A—C2B	108.7 (4)	C11B—C16B—H16B	120.1
N4A—C3A—C2A	112.7 (2)	C15B—C16B—H16B	120.1
C4A—C3A—C2A	121.8 (2)

C11—C1—C2—C3	−176.70 (11)	N4A—N5A—C6A—O6A	177.47 (12)
C1—C2—C3—N4	−109.73 (14)	N4A—N5A—C6A—N6A	−3.92 (19)
C1—C2—C3—C4	69.69 (16)	C2A—C1A—C11A—C16A	128.8 (4)
C4—C3—N4—N5	1.78 (19)	C2A—C1A—C11A—C12A	−54.5 (5)
C2—C3—N4—N5	−178.85 (11)	C16A—C11A—C12A—C13A	2.6 (12)
C3—N4—N5—C6	165.49 (12)	C1A—C11A—C12A—C13A	−174.3 (10)
N4—N5—C6—O6	−173.10 (12)	C11A—C12A—C13A—C14A	0 (2)
N4—N5—C6—N6	7.79 (18)	C12A—C13A—C14A—C15A	−2 (2)
C2—C1—C11—C16	95.70 (15)	C13A—C14A—C15A—C16A	1.5 (19)
C2—C1—C11—C12	−83.43 (16)	C14A—C15A—C16A—C11A	0.8 (14)
C16—C11—C12—C13	0.6 (2)	C12A—C11A—C16A—C15A	−2.7 (8)
C1—C11—C12—C13	179.79 (13)	C1A—C11A—C16A—C15A	174.1 (6)
C11—C12—C13—C14	−0.6 (2)	N4A—C3A—C2B—C1B	−5.9 (8)
C12—C13—C14—C15	0.3 (2)	C4A—C3A—C2B—C1B	162.5 (5)
C13—C14—C15—C16	−0.1 (2)	C2A—C3A—C2B—C1B	−64.6 (14)
C12—C11—C16—C15	−0.4 (2)	C11B—C1B—C2B—C3A	177.0 (5)
C1—C11—C16—C15	−179.60 (13)	C2B—C1B—C11B—C12B	−142.5 (8)
C14—C15—C16—C11	0.2 (2)	C2B—C1B—C11B—C16B	40.5 (7)
C11A—C1A—C2A—C3A	175.1 (4)	C16B—C11B—C12B—C13B	−1 (2)
C1A—C2A—C3A—N4A	−99.4 (3)	C1B—C11B—C12B—C13B	−177.9 (16)
C1A—C2A—C3A—C4A	85.9 (4)	C11B—C12B—C13B—C14B	1 (4)
C1A—C2A—C3A—C2B	31.2 (14)	C12B—C13B—C14B—C15B	0 (5)
C4A—C3A—N4A—N5A	−0.1 (3)	C13B—C14B—C15B—C16B	−1 (4)
C2B—C3A—N4A—N5A	166.5 (4)	C12B—C11B—C16B—C15B	0.2 (13)
C2A—C3A—N4A—N5A	−174.6 (2)	C1B—C11B—C16B—C15B	177.2 (9)
C3A—N4A—N5A—C6A	−172.71 (13)	C14B—C15B—C16B—C11B	1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O6A	0.872 (17)	2.153 (17)	3.0163 (14)	170.3 (15)
N6—H6A···O6ⁱ	0.861 (18)	2.331 (18)	3.0881 (16)	146.9 (15)
N6—H6B···N4ⁱⁱ	0.874 (17)	2.262 (17)	3.1273 (17)	170.2 (14)
N5A—H5A···O6	0.877 (17)	2.089 (18)	2.9492 (15)	166.8 (14)
N6A—H6D···O6Aⁱⁱⁱ	0.917 (19)	2.01 (2)	2.9265 (16)	176.6 (16)

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅N₃O
M_r	205.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	14.059 (1), 7.1282 (9), 22.621 (2)
β (°)	94.148 (1)
V (Å³)	2261.0 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.72 × 0.58 × 0.12

Data collection
Diffractometer	Siemens CCD three-circle diffractometer
Absorption correction	Empirical (using intensity measurements) (SADABS; Sheldrick, 1996)
T_min, T_max	0.944, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	33568, 5099, 4035
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.109, 1.07
No. of reflections	5099
No. of parameters	371
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20

Computer programs: SMART (Siemens, 1995), SMART, SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O6A	0.872 (17)	2.153 (17)	3.0163 (14)	170.3 (15)
N6—H6A···O6ⁱ	0.861 (18)	2.331 (18)	3.0881 (16)	146.9 (15)
N6—H6B···N4ⁱⁱ	0.874 (17)	2.262 (17)	3.1273 (17)	170.2 (14)
N5A—H5A···O6	0.877 (17)	2.089 (18)	2.9492 (15)	166.8 (14)
N6A—H6D···O6Aⁱⁱⁱ	0.917 (19)	2.01 (2)	2.9265 (16)	176.6 (16)

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1, −y+2, −z+1.

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4-Phenyl­butan-2-one semi­carbazone

Supporting information

4-Phenylbutan-2-one semicarbazone