N-(Benzothia­zol-2-yl)butyramide

Saeed, S.; Bhatti, M.H.; Jones, P.G.

doi:10.1107/S1600536808020667

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1486

doi:10.1107/S1600536808020667

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N-(Benzothiazol-2-yl)butyramide

Sohail Saeed,^a ^* Moazzam Hussain Bhatti ^a and Peter G. Jones ^b

^aDepartment of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan, and ^bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany
^*Correspondence e-mail: sohail262001@yahoo.com

(Received 21 June 2008; accepted 4 July 2008; online 12 July 2008)

The title compound, C₁₁H₁₂N₂OS, was synthesized from 2-aminobenzothiazole and butanoyl chloride in anhydrous acetone. In the crystal structure, molecules are linked by N—H⋯N and C—H⋯O hydrogen bonds and by C—H⋯π interactions.

Related literature

For related literature, see: Butt et al. (2005 ); Im & Jung (2000 ); Yang et al. (2002 ); Ataei et al. (2005 ).

Experimental

Crystal data

C₁₁H₁₂N₂OS
M_r = 220.29
Triclinic, $[P \overline 1]$
a = 5.2916 (4) Å
b = 7.4462 (8) Å
c = 13.565 (1) Å
α = 92.618 (7)°
β = 90.607 (6)°
γ = 107.185 (8)°
V = 509.92 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 100 (2) K
0.35 × 0.20 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.977, T_max = 1.000 (expected range = 0.963–0.986)
8577 measured reflections
2728 independent reflections
2172 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.090
S = 0.99
2728 reflections
141 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.84 (2)	2.40 (2)	3.232 (2)	172 (1)
C10—H10⋯Oⁱⁱ	0.95	2.46	3.277 (2)	144
C2—H2B⋯Cg1ⁱⁱⁱ	0.99	2.66	3.56	152
C3—H3B⋯Cg1^iv	0.99	2.64	3.47	142
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y, -z+1. Cg1 is the centroid of the C6–C11 ring.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020667/im2075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020667/im2075Isup2.hkl

checkCIF report

Comment top

High temperature polymers have received much attention due to the increasing demands for the replacement of ceramics and metals (Ataei et al., 2005). However, in many cases, they are insoluble and do not melt below their decomposition temperature,which restricts their applications (Im & Jung, 2000). Thus, many studies have focused on obtaining aromatic polymers that are processable by conventional techniques (Yang et al., 2002). The title compound, (I), is a precursor for an attempt to synthesize polyimides (Butt et al., 2005), imidazole derivatives and transition metal complexes. The entire molecule (except H atoms) is planar within a mean deviation of 0.03 Å. Molecules are connected in ribbons parallel to [210] by classical hydrogen bonds N1—H1···N2 and additional weak hydrogen bonds C10—H10···O. S atoms of neighbouring molecules approach each other to 3.5267 (7) Å. Perpendicular to the ribbons are two C—H···π interactions (Table 1, Fig.2). The molecular structure of the title compound is depicted in Figure 1.

Related literature top

For related literature, see: Butt et al. (2005); Im & Jung (2000); Yang et al. (2002; Ataei et al., 2005).

Experimental top

A mixture of butanoyl chloride (0.1 mol) and 2-aminobenzothiazole (0.1 mol) in anhydrous acetone (75 ml) was refluxed for 20 h. After cooling, the reaction mixture was poured in acidified cold water. The resulting dark brown solid was filtered and washed with cold acetone. Crystals of the title compound (I) suitable for X-Ray analysis were obtained after re-crystallization of the solid from ethanol (2.36 g, 79%). m.p.447 K.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Ellipsoids represent 50% probability levels.
	Fig. 2. Packing diagram of I showing classical and "weak" H bonds and S···S contacts as thin dashed bonds. View direction is perpendicular to [102].

N-(Benzothiazol-2-yl)butyramide top

Crystal data top

C₁₁H₁₂N₂OS	Z = 2
M_r = 220.29	F(000) = 232
Triclinic, P1	D_x = 1.435 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2916 (4) Å	Cell parameters from 4460 reflections
b = 7.4462 (8) Å	θ = 2.9–30.7°
c = 13.565 (1) Å	µ = 0.29 mm⁻¹
α = 92.618 (7)°	T = 100 K
β = 90.607 (6)°	Plate, yellow
γ = 107.185 (8)°	0.35 × 0.20 × 0.05 mm
V = 509.92 (8) Å³

Data collection top

Oxford Diffraction Xcalibur S diffractometer	2728 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2172 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 16.1057 pixels mm^-1	θ_max = 30.0°, θ_min = 2.9°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −9→10
T_min = 0.977, T_max = 1.000	l = −19→18
8577 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0544P)²]
2728 reflections	(Δ/σ)_max = 0.001
141 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₁H₁₂N₂OS	γ = 107.185 (8)°
M_r = 220.29	V = 509.92 (8) Å³
Triclinic, P1	Z = 2
a = 5.2916 (4) Å	Mo Kα radiation
b = 7.4462 (8) Å	µ = 0.29 mm⁻¹
c = 13.565 (1) Å	T = 100 K
α = 92.618 (7)°	0.35 × 0.20 × 0.05 mm
β = 90.607 (6)°

Data collection top

Oxford Diffraction Xcalibur S diffractometer	2728 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	2172 reflections with I > 2σ(I)
T_min = 0.977, T_max = 1.000	R_int = 0.035
8577 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.41 e Å⁻³
2728 reflections	Δρ_min = −0.26 e Å⁻³
141 parameters

Special details top

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.

Non-bonded distance

3.5267 (0.0007) S - S_$2 $2 - x + 2, -y + 1, -z + 1

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.9402 (0.0016) x + 6.9014 (0.0013) y + 2.6739 (0.0017) z = 1.5591 (0.0012)

* -0.0482 (0.0011) N1 * -0.0353 (0.0010) N2 * 0.0176 (0.0010) O * -0.0420 (0.0006) S * 0.0121 (0.0012) C1 * 0.0438 (0.0012) C2 * 0.0205 (0.0013) C3 * 0.0008 (0.0013) C4 * -0.0386 (0.0013) C5 * -0.0125 (0.0012) C6 * 0.0334 (0.0011) C7 * 0.0608 (0.0012) C8 * 0.0306 (0.0012) C9 * -0.0160 (0.0011) C10 * -0.0269 (0.0012) C11

Rms deviation of fitted atoms = 0.0332

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
N1	0.3005 (2)	0.17657 (16)	0.43971 (8)	0.0115 (2)
H1	0.142 (3)	0.110 (2)	0.4321 (11)	0.019 (4)*
N2	0.2856 (2)	0.10743 (16)	0.60669 (8)	0.0110 (2)
O	0.65683 (18)	0.36649 (14)	0.36601 (7)	0.0168 (2)
S	0.74719 (6)	0.32370 (5)	0.55350 (2)	0.01216 (11)
C1	0.2219 (3)	0.2887 (2)	0.08646 (10)	0.0186 (3)
H1A	0.1669	0.1526	0.0710	0.028*
H1B	0.3186	0.3540	0.0309	0.028*
H1C	0.0653	0.3306	0.0981	0.028*
C2	0.4007 (3)	0.3337 (2)	0.17869 (9)	0.0141 (3)
H2A	0.5602	0.2931	0.1665	0.017*
H2B	0.4589	0.4715	0.1934	0.017*
C3	0.2581 (2)	0.2353 (2)	0.26720 (9)	0.0120 (3)
H3A	0.1017	0.2794	0.2799	0.014*
H3B	0.1935	0.0983	0.2506	0.014*
C4	0.4267 (2)	0.26838 (19)	0.35982 (9)	0.0118 (3)
C5	0.4162 (2)	0.19131 (19)	0.53257 (9)	0.0102 (3)
C6	0.4520 (2)	0.14896 (19)	0.69100 (9)	0.0109 (3)
C7	0.3830 (3)	0.0893 (2)	0.78621 (9)	0.0130 (3)
H7	0.2093	0.0123	0.7986	0.016*
C8	0.5711 (3)	0.1442 (2)	0.86165 (9)	0.0142 (3)
H8	0.5244	0.1051	0.9264	0.017*
C9	0.8288 (3)	0.2560 (2)	0.84506 (10)	0.0145 (3)
H9	0.9547	0.2907	0.8983	0.017*
C10	0.9017 (3)	0.3166 (2)	0.75156 (10)	0.0133 (3)
H10	1.0764	0.3922	0.7395	0.016*
C11	0.7103 (3)	0.26286 (19)	0.67562 (9)	0.0110 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0082 (5)	0.0137 (6)	0.0107 (5)	0.0002 (5)	−0.0016 (4)	0.0019 (4)
N2	0.0099 (5)	0.0118 (6)	0.0109 (5)	0.0026 (4)	0.0002 (4)	0.0006 (4)
O	0.0122 (4)	0.0210 (6)	0.0135 (5)	−0.0013 (4)	0.0001 (4)	0.0041 (4)
S	0.00957 (16)	0.0143 (2)	0.01083 (16)	0.00062 (12)	0.00010 (11)	0.00174 (12)
C1	0.0215 (7)	0.0210 (8)	0.0123 (6)	0.0046 (6)	−0.0013 (5)	0.0027 (6)
C2	0.0137 (6)	0.0167 (8)	0.0120 (6)	0.0043 (6)	0.0009 (5)	0.0029 (5)
C3	0.0106 (6)	0.0132 (7)	0.0118 (6)	0.0030 (5)	−0.0010 (5)	0.0010 (5)
C4	0.0130 (6)	0.0107 (7)	0.0122 (6)	0.0041 (5)	0.0009 (5)	0.0006 (5)
C5	0.0104 (6)	0.0090 (7)	0.0116 (6)	0.0034 (5)	0.0000 (4)	0.0006 (5)
C6	0.0115 (6)	0.0102 (7)	0.0120 (6)	0.0048 (5)	−0.0003 (5)	−0.0007 (5)
C7	0.0116 (6)	0.0137 (7)	0.0139 (6)	0.0036 (5)	0.0018 (5)	0.0025 (5)
C8	0.0164 (6)	0.0166 (8)	0.0110 (6)	0.0067 (6)	0.0008 (5)	0.0024 (5)
C9	0.0142 (6)	0.0155 (8)	0.0142 (6)	0.0055 (5)	−0.0040 (5)	−0.0007 (5)
C10	0.0123 (6)	0.0125 (7)	0.0148 (6)	0.0036 (5)	−0.0012 (5)	−0.0004 (5)
C11	0.0120 (6)	0.0111 (7)	0.0108 (6)	0.0048 (5)	0.0009 (4)	0.0013 (5)

Geometric parameters (Å, º) top

N1—C4	1.3788 (16)	C9—C10	1.3858 (18)
N1—C5	1.3803 (16)	C10—C11	1.3956 (18)
N2—C5	1.3022 (16)	N1—H1	0.841 (17)
N2—C6	1.4015 (16)	C1—H1A	0.9800
O—C4	1.2209 (16)	C1—H1B	0.9800
S—C11	1.7351 (13)	C1—H1C	0.9800
S—C5	1.7501 (13)	C2—H2A	0.9900
C1—C2	1.5238 (18)	C2—H2B	0.9900
C2—C3	1.5236 (17)	C3—H3A	0.9900
C3—C4	1.5011 (17)	C3—H3B	0.9900
C6—C7	1.4019 (17)	C7—H7	0.9500
C6—C11	1.4027 (18)	C8—H8	0.9500
C7—C8	1.3802 (18)	C9—H9	0.9500
C8—C9	1.3988 (19)	C10—H10	0.9500

C4—N1—C5	123.92 (11)	C2—C1—H1B	109.5
C5—N2—C6	108.90 (10)	H1A—C1—H1B	109.5
C11—S—C5	87.62 (6)	C2—C1—H1C	109.5
C3—C2—C1	111.29 (11)	H1A—C1—H1C	109.5
C4—C3—C2	113.98 (11)	H1B—C1—H1C	109.5
O—C4—N1	121.46 (12)	C3—C2—H2A	109.4
O—C4—C3	124.23 (11)	C1—C2—H2A	109.4
N1—C4—C3	114.30 (11)	C3—C2—H2B	109.4
N2—C5—N1	121.66 (11)	C1—C2—H2B	109.4
N2—C5—S	118.00 (9)	H2A—C2—H2B	108.0
N1—C5—S	120.34 (9)	C4—C3—H3A	108.8
N2—C6—C7	126.34 (12)	C2—C3—H3A	108.8
N2—C6—C11	114.83 (11)	C4—C3—H3B	108.8
C7—C6—C11	118.83 (12)	C2—C3—H3B	108.8
C8—C7—C6	119.00 (12)	H3A—C3—H3B	107.7
C7—C8—C9	121.58 (12)	C8—C7—H7	120.5
C10—C9—C8	120.45 (12)	C6—C7—H7	120.5
C9—C10—C11	117.88 (12)	C7—C8—H8	119.2
C10—C11—C6	122.25 (12)	C9—C8—H8	119.2
C10—C11—S	127.12 (10)	C10—C9—H9	119.8
C6—C11—S	110.63 (9)	C8—C9—H9	119.8
C4—N1—H1	118.4 (11)	C9—C10—H10	121.1
C5—N1—H1	117.7 (11)	C11—C10—H10	121.1
C2—C1—H1A	109.5

C1—C2—C3—C4	177.95 (12)	N2—C6—C7—C8	−179.52 (13)
C5—N1—C4—O	2.2 (2)	C11—C6—C7—C8	−0.1 (2)
C5—N1—C4—C3	−178.25 (12)	C6—C7—C8—C9	−0.6 (2)
C2—C3—C4—O	0.8 (2)	C7—C8—C9—C10	0.6 (2)
C2—C3—C4—N1	−178.73 (11)	C8—C9—C10—C11	0.2 (2)
C6—N2—C5—N1	−179.44 (12)	C9—C10—C11—C6	−1.0 (2)
C6—N2—C5—S	0.99 (15)	C9—C10—C11—S	178.35 (10)
C4—N1—C5—N2	177.35 (12)	N2—C6—C11—C10	−179.60 (12)
C4—N1—C5—S	−3.09 (18)	C7—C6—C11—C10	0.9 (2)
C11—S—C5—N2	−0.39 (11)	N2—C6—C11—S	0.99 (15)
C11—S—C5—N1	−179.97 (12)	C7—C6—C11—S	−178.49 (10)
C5—N2—C6—C7	178.19 (13)	C5—S—C11—C10	−179.73 (14)
C5—N2—C6—C11	−1.25 (17)	C5—S—C11—C6	−0.35 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.84 (2)	2.40 (2)	3.232 (2)	172 (1)
C10—H10···Oⁱⁱ	0.95	2.46	3.277 (2)	144
C2—H2B···Cent(C6–C11)ⁱⁱⁱ	0.99	2.66	3.56	152
C3—H3B···Cent(C6–C11)^iv	0.99	2.64	3.47	142

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₂OS
M_r	220.29
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.2916 (4), 7.4462 (8), 13.565 (1)
α, β, γ (°)	92.618 (7), 90.607 (6), 107.185 (8)
V (Å³)	509.92 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.35 × 0.20 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcalibur S diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.977, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8577, 2728, 2172
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.091, 0.99
No. of reflections	2728
No. of parameters	141
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.26

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1994).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.84 (2)	2.40 (2)	3.232 (2)	172 (1)
C10—H10···Oⁱⁱ	0.95	2.46	3.277 (2)	144.1
C2—H2B···Cent(C6–C11)ⁱⁱⁱ	0.99	2.66	3.56	152
C3—H3B···Cent(C6–C11)^iv	0.99	2.64	3.47	142

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

Acknowledgements

The authors are grateful to Allama Iqbal Open University, Islamabad, Pakistan, for providing the research and analytical laboratory facilities.

References

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