(E)-1-(4-Chloro­phen­yl)ethanone semi­carbazone

Fun, H.-K.; Quah, C.K.; Padaki, M.; Malladi, S.; Isloor, A.M.

doi:10.1107/S160053680902279X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1634-o1635

doi:10.1107/S160053680902279X

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(E)-1-(4-Chlorophenyl)ethanone semicarbazone

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Mahesh Padaki,^b Shridhar Malladi ^b and Arun M. Isloor ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 11 June 2009; accepted 13 June 2009; online 20 June 2009)

In the title compound, C₉H₁₀ClN₃O, the semicarbazone group is approximately planar, with an r.m.s. deviation from the mean plane of 0.054 (1) Å. The dihedral angle between the least-squares planes through the semicarbazone group and the benzene ring is 30.46 (5)°. In the solid state, molecules are linked via intermolecular N—H⋯O and N—H⋯N hydrogen bonds, generating R₂²(9) ring motifs which, together with R₂²(8) ring motifs formed by pairs of intermolecular N—H⋯O hydrogen bonds, lead to the formation of a seldom-observed molecular trimer. Furthermore, N—H⋯O hydrogen bonds form R₂¹(7) ring motifs with C—H⋯O hydrogen bonds, further consolidating the crystal structure. Molecules are linked by these intermolecular interactions, forming two-dimensional networks parallel to (100).

Related literature

For the synthetic utility and applications of semicarbazone derivatives, see: Warren et al. (1977 ); Chandra & Gupta (2005 ); Jain et al. (2002 ); Pilgram (1978 ); Yogeeswari et al. (2004 ). For a related structure, see: Fun et al. (2009 ). For the preparation, see: Furniss et al. (1978 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₉H₁₀ClN₃O
M_r = 211.65
Monoclinic, C 2/c
a = 21.8191 (4) Å
b = 7.0484 (1) Å
c = 13.7249 (2) Å
β = 109.633 (1)°
V = 1988.04 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 100 K
0.41 × 0.20 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.867, T_max = 0.991
28636 measured reflections
3539 independent reflections
2912 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.101
S = 1.04
3539 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1ⁱ	0.884 (19)	2.007 (19)	2.8866 (12)	173.3 (19)
N3—H1N3⋯N1ⁱⁱ	0.835 (18)	2.264 (18)	3.0904 (14)	170.5 (16)
N3—H2N3⋯O1ⁱⁱⁱ	0.826 (17)	2.316 (17)	3.0499 (13)	148.4 (15)
C9—H9C⋯O1ⁱ	0.94 (2)	2.55 (2)	3.2162 (16)	128.1 (16)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902279X/sj2631sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902279X/sj2631Isup2.hkl

checkCIF report

Comment top

In organic chemistry, a semicarbazone is a derivative of an aldehyde or ketone formed by a condensation between a ketone or aldehyde and semicarbazide. Semicarbazones find numerous applications in the field of synthetic chemistry, such as medicinal chemistry (Warren et al., 1977), organometalics (Chandra & Gupta, 2005), polymers (Jain et al., 2002) and herbicides (Pilgram, 1978). 4-Sulphamoylphenyl semicarbazones were synthesized and were found to possess anticonvulsant activity (Yogeeswari et al., 2004). Herein we report the crystal structure of the title semicarbazone which may have commercial and synthetic importance.

The bond lengths (Allen et al., 1987) and angles in the molecule (Fig. 1) are within normal ranges, and are comparable to those observed in a closely related structure (Fun et al., 2009). The semicarbazone group (C9/C6/C7/N1/N2/C8/O1/N3) is approximately planar, with an r.m.s. deviation of 0.054 (1) Å for atom N2 while the dihedral angle between the least-squares planes through the semicarbazone group and the benzene ring is 30.46 (5)°.

In the solid state, the molecules are linked via intermolecular N3—H2N3···O1 and N3—H1N3···N1 hydrogen bonds to generate R₂²(9) ring motifs which, together with the R₂²(8) ring motifs formed by pairs of intermolecular N2—H1N2···O1 hydrogen bonds, lead to the formation of a seldom-observed molecular trimer (Fig. 2). Furthermore, N2—H1N2···O1 hydrogen bonds form R₂¹(7) ring motifs (Fig. 2) with C9—H9C···O1 hydrogen bonds to further consolidated the crystal structure. The molecules are linked by these intermolecular interactions to form two-dimensional networks parallel to the (1 0 0) plane.

Related literature top

For the synthetic utility and applications of semicarbazone derivatives, see: Warren et al. (1977); Chandra & Gupta (2005); Jain et al. (2002); Pilgram (1978); Yogeeswari et al. (2004). For a related structure, see: Fun et al. (2009). For the preparation, see: Furniss et al. (1978). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

0.780 g (7.0 mmol) of semicarbazide hydrochloride and 0.698 g (8.5 mmol) of crystallized sodium acetate was dissolved in 10 ml of water (Furniss et al., 1978). The reaction mixture was stirred at room temperature for 10 minutes. To this (1 g, 6.5 mmol) of 4-choloacetophenone was added and shaken well. A little alcohol was added to dissolve the turbidity. It was shaken for 10 more minutes and allowed to stand. The semicarbazone crystallizes on standing for 6 h. The separated crystals were filtered, washed with cold water and recrystallized from alcohol. Yield was found to be 1.1 g, 80.35%. M.p. 478–479 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008)L; molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Fig. 2. Part of the crystal packing of the title compound, viewed along the a axis, showing the formation of a molecular trimer. Atom-numbering is shown for those non-H atoms involved in hydrogen bonds and intermolecular interactions are shown as dashed lines. Molecule A is is related to molecules B and C via symmetry codes of -x + 1/2, -y + 1/2, -z and -x + 1/2, y + 1/2, -z + 1/2, respectively.

(E)-1-(4-Chlorophenyl)ethanone semicarbazone top

Crystal data top

C₉H₁₀ClN₃O	F(000) = 880
M_r = 211.65	D_x = 1.414 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6351 reflections
a = 21.8191 (4) Å	θ = 3.1–32.1°
b = 7.0484 (1) Å	µ = 0.35 mm⁻¹
c = 13.7249 (2) Å	T = 100 K
β = 109.633 (1)°	Plate, colourless
V = 1988.04 (6) Å³	0.41 × 0.20 × 0.03 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3539 independent reflections
Radiation source: fine-focus sealed tube	2912 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ϕ and ω scans	θ_max = 32.3°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −32→32
T_min = 0.867, T_max = 0.991	k = −10→10
28636 measured reflections	l = −20→20

Refinement top

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) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.049P)² + 1.2937P] where P = (F_o² + 2F_c²)/3
3539 reflections	(Δ/σ)_max = 0.001
167 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₉H₁₀ClN₃O	V = 1988.04 (6) Å³
M_r = 211.65	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.8191 (4) Å	µ = 0.35 mm⁻¹
b = 7.0484 (1) Å	T = 100 K
c = 13.7249 (2) Å	0.41 × 0.20 × 0.03 mm
β = 109.633 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3539 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2912 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.991	R_int = 0.052
28636 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.45 e Å⁻³
3539 reflections	Δρ_min = −0.27 e Å⁻³
167 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.023375 (16)	−0.37949 (4)	0.13113 (2)	0.02330 (9)
O1	0.28038 (4)	0.80096 (12)	0.13075 (6)	0.01675 (17)
N1	0.18652 (5)	0.38677 (13)	0.08164 (7)	0.01332 (18)
N2	0.22047 (5)	0.53956 (13)	0.06342 (7)	0.01416 (18)
N3	0.24395 (6)	0.61942 (14)	0.23627 (8)	0.0176 (2)
C1	0.11370 (6)	−0.05633 (16)	−0.01844 (9)	0.0167 (2)
C2	0.08397 (6)	−0.21004 (16)	0.01146 (10)	0.0178 (2)
C3	0.06045 (6)	−0.18847 (16)	0.09274 (9)	0.0172 (2)
C4	0.06590 (6)	−0.01713 (17)	0.14505 (9)	0.0184 (2)
C5	0.09612 (6)	0.13476 (16)	0.11541 (9)	0.0167 (2)
C6	0.12052 (6)	0.11705 (15)	0.03359 (9)	0.0136 (2)
C7	0.15469 (6)	0.27915 (15)	0.00516 (9)	0.0137 (2)
C8	0.24965 (6)	0.65995 (15)	0.14448 (8)	0.0136 (2)
C9	0.15172 (7)	0.30648 (18)	−0.10430 (9)	0.0189 (2)
H1	0.1299 (8)	−0.071 (2)	−0.0751 (13)	0.022 (4)*
H2	0.0807 (8)	−0.332 (3)	−0.0235 (13)	0.029 (4)*
H4	0.0472 (8)	−0.007 (2)	0.2047 (13)	0.026 (4)*
H5	0.0998 (8)	0.254 (2)	0.1502 (13)	0.024 (4)*
H9A	0.1211 (11)	0.237 (3)	−0.1478 (18)	0.053 (6)*
H9B	0.1901 (12)	0.271 (3)	−0.1107 (18)	0.064 (7)*
H9C	0.1416 (9)	0.433 (3)	−0.1261 (15)	0.036 (5)*
H1N2	0.2197 (8)	0.579 (3)	0.0019 (14)	0.028 (4)*
H1N3	0.2668 (8)	0.684 (2)	0.2863 (13)	0.022 (4)*
H2N3	0.2271 (8)	0.522 (2)	0.2487 (12)	0.020 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02608 (17)	0.01993 (15)	0.02367 (16)	−0.00699 (11)	0.00806 (12)	0.00422 (10)
O1	0.0227 (4)	0.0154 (4)	0.0128 (4)	−0.0054 (3)	0.0067 (3)	−0.0010 (3)
N1	0.0157 (4)	0.0121 (4)	0.0120 (4)	−0.0013 (3)	0.0044 (3)	0.0007 (3)
N2	0.0202 (5)	0.0127 (4)	0.0100 (4)	−0.0042 (3)	0.0056 (4)	−0.0007 (3)
N3	0.0272 (6)	0.0163 (4)	0.0102 (4)	−0.0065 (4)	0.0076 (4)	−0.0015 (3)
C1	0.0176 (5)	0.0165 (5)	0.0163 (5)	−0.0024 (4)	0.0064 (4)	−0.0024 (4)
C2	0.0183 (6)	0.0141 (5)	0.0204 (6)	−0.0024 (4)	0.0055 (4)	−0.0019 (4)
C3	0.0165 (5)	0.0148 (5)	0.0188 (5)	−0.0024 (4)	0.0039 (4)	0.0037 (4)
C4	0.0200 (6)	0.0194 (5)	0.0166 (5)	−0.0019 (4)	0.0074 (4)	0.0013 (4)
C5	0.0200 (6)	0.0151 (5)	0.0158 (5)	−0.0013 (4)	0.0073 (4)	−0.0010 (4)
C6	0.0138 (5)	0.0142 (5)	0.0121 (5)	−0.0004 (4)	0.0034 (4)	0.0013 (4)
C7	0.0158 (5)	0.0127 (4)	0.0121 (5)	−0.0006 (4)	0.0040 (4)	0.0003 (4)
C8	0.0164 (5)	0.0129 (4)	0.0109 (5)	−0.0002 (4)	0.0040 (4)	−0.0005 (4)
C9	0.0266 (7)	0.0185 (5)	0.0124 (5)	−0.0052 (5)	0.0077 (5)	−0.0008 (4)

Geometric parameters (Å, º) top

Cl1—C3	1.7410 (12)	C2—C3	1.3842 (18)
O1—C8	1.2481 (13)	C2—H2	0.977 (18)
N1—C7	1.2922 (14)	C3—C4	1.3895 (17)
N1—N2	1.3768 (13)	C4—C5	1.3882 (16)
N2—C8	1.3737 (14)	C4—H4	1.033 (17)
N2—H1N2	0.883 (18)	C5—C6	1.4006 (16)
N3—C8	1.3378 (14)	C5—H5	0.958 (17)
N3—H1N3	0.835 (18)	C6—C7	1.4863 (15)
N3—H2N3	0.826 (17)	C7—C9	1.4943 (16)
C1—C2	1.3935 (16)	C9—H9A	0.88 (2)
C1—C6	1.3979 (15)	C9—H9B	0.91 (2)
C1—H1	0.963 (16)	C9—H9C	0.94 (2)

C7—N1—N2	119.12 (9)	C4—C5—C6	120.81 (11)
C8—N2—N1	117.86 (9)	C4—C5—H5	120.0 (10)
C8—N2—H1N2	115.9 (12)	C6—C5—H5	119.1 (10)
N1—N2—H1N2	125.4 (12)	C1—C6—C5	118.92 (10)
C8—N3—H1N3	116.1 (12)	C1—C6—C7	120.97 (10)
C8—N3—H2N3	124.2 (11)	C5—C6—C7	120.08 (10)
H1N3—N3—H2N3	118.0 (16)	N1—C7—C6	114.71 (10)
C2—C1—C6	120.63 (11)	N1—C7—C9	124.82 (10)
C2—C1—H1	119.1 (10)	C6—C7—C9	120.46 (10)
C6—C1—H1	120.3 (10)	O1—C8—N3	122.47 (10)
C3—C2—C1	119.16 (11)	O1—C8—N2	119.73 (10)
C3—C2—H2	120.4 (10)	N3—C8—N2	117.80 (10)
C1—C2—H2	120.4 (10)	C7—C9—H9A	112.1 (14)
C2—C3—C4	121.43 (11)	C7—C9—H9B	109.4 (15)
C2—C3—Cl1	119.65 (9)	H9A—C9—H9B	107 (2)
C4—C3—Cl1	118.92 (9)	C7—C9—H9C	111.6 (11)
C5—C4—C3	119.04 (11)	H9A—C9—H9C	105.6 (19)
C5—C4—H4	122.2 (10)	H9B—C9—H9C	110.9 (19)
C3—C4—H4	118.7 (10)

C7—N1—N2—C8	175.03 (10)	C4—C5—C6—C7	−177.97 (11)
C6—C1—C2—C3	0.79 (18)	N2—N1—C7—C6	179.22 (9)
C1—C2—C3—C4	−0.05 (18)	N2—N1—C7—C9	0.30 (17)
C1—C2—C3—Cl1	−179.84 (9)	C1—C6—C7—N1	−146.43 (11)
C2—C3—C4—C5	−0.55 (19)	C5—C6—C7—N1	31.82 (15)
Cl1—C3—C4—C5	179.24 (9)	C1—C6—C7—C9	32.55 (16)
C3—C4—C5—C6	0.41 (18)	C5—C6—C7—C9	−149.20 (12)
C2—C1—C6—C5	−0.92 (18)	N1—N2—C8—O1	−179.37 (10)
C2—C1—C6—C7	177.35 (11)	N1—N2—C8—N3	0.92 (16)
C4—C5—C6—C1	0.32 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.884 (19)	2.007 (19)	2.8866 (12)	173.3 (19)
N3—H1N3···N1ⁱⁱ	0.835 (18)	2.264 (18)	3.0904 (14)	170.5 (16)
N3—H2N3···O1ⁱⁱⁱ	0.826 (17)	2.316 (17)	3.0499 (13)	148.4 (15)
C9—H9C···O1ⁱ	0.94 (2)	2.55 (2)	3.2162 (16)	128.1 (16)

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

Experimental details

Crystal data
Chemical formula	C₉H₁₀ClN₃O
M_r	211.65
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	21.8191 (4), 7.0484 (1), 13.7249 (2)
β (°)	109.633 (1)
V (Å³)	1988.04 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.41 × 0.20 × 0.03

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.867, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	28636, 3539, 2912
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.751

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.101, 1.04
No. of reflections	3539
No. of parameters	167
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.27

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008)L, SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.884 (19)	2.007 (19)	2.8866 (12)	173.3 (19)
N3—H1N3···N1ⁱⁱ	0.835 (18)	2.264 (18)	3.0904 (14)	170.5 (16)
N3—H2N3···O1ⁱⁱⁱ	0.826 (17)	2.316 (17)	3.0499 (13)	148.4 (15)
C9—H9C···O1ⁱ	0.94 (2)	2.55 (2)	3.2162 (16)	128.1 (16)

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). CKQ thanks USM for a Research Fellowship. AMI is grateful to the Head of the Department of Chemistry and the Director, NITK, Surathkal, India, for providing research facilities.

References

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