N-(Benzothia-zol-2-yl)-3-chloro-benzamide.

The title mol-ecule, C(14)H(9)ClN(2)OS, exists in the solid state in its amide form with a typical C=O bond length, as well as shortened C-N bonds. The plane containing the HNCO atoms subtends dihedral angles of 12.3 (4) and 8.1 (3)° with the planes of the phenyl ring and benzothia-zole group, respectively, whereas the dihedral angle between the planes of the phenyl ring and the benzothia-zole group is 5.96 (6)°. In the crystal, mol-ecules form inter-molecular N-H⋯N hydrogen bonds, generating independent scissor-like R(2) (2)(8) dimers.

Related literature

For geometric data, see: Allen et al. (1987 ▶); For related structures, see: Garden et al. (2005 ▶); Wardell et al. (2005 ▶).

Experimental

Crystal data

C14H9ClN2OS

M = 288.74

Monoclinic,

a = 26.6613 (19) Å

b = 7.5766 (5) Å

c = 12.6729 (10) Å

β = 99.729 (6)°

V = 2523.1 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.46 mm−1

T = 173 K

0.39 × 0.38 × 0.35 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan [MULABS (Spek, 2009 ▶); Blessing, 1995 ▶)] T min = 0.841, T max = 0.856

9132 measured reflections

2352 independent reflections

2084 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.079

S = 1.03

2352 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.23 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016481/hg2508sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016481/hg2508Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H9ClN2OS	F(000) = 1184
Mr = 288.74	Dx = 1.520 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8429 reflections
a = 26.6613 (19) Å	θ = 3.6–25.9°
b = 7.5766 (5) Å	µ = 0.46 mm−1
c = 12.6729 (10) Å	T = 173 K
β = 99.729 (6)°	Block, light yellow
V = 2523.1 (3) Å3	0.39 × 0.38 × 0.35 mm
Z = 8

Stoe IPDS II two-circle diffractometer	2352 independent reflections
Radiation source: fine-focus sealed tube	2084 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan [MULABS (Spek, 2009); Blessing, 1995)]	h = −32→32
Tmin = 0.841, Tmax = 0.856	k = −8→9
9132 measured reflections	l = −15→15

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.051P)2 + 0.8598P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2352 reflections	Δρmax = 0.28 e Å−3
177 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (6)

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
Cl1	0.762196 (14)	0.69837 (6)	0.65336 (3)	0.03053 (14)
S1	0.500738 (13)	0.23662 (5)	0.45176 (3)	0.01915 (13)
O1	0.58693 (4)	0.40431 (15)	0.51591 (8)	0.0241 (3)
N1	0.54529 (4)	0.34541 (16)	0.65241 (10)	0.0178 (3)
H1	0.5448 (7)	0.325 (2)	0.7252 (17)	0.032 (5)*
C1	0.58602 (5)	0.41061 (19)	0.61190 (11)	0.0179 (3)
N2	0.46256 (4)	0.23590 (16)	0.62817 (10)	0.0185 (3)
C2	0.50288 (5)	0.27653 (19)	0.58813 (11)	0.0167 (3)
C3	0.42583 (5)	0.16277 (19)	0.54925 (12)	0.0185 (3)
C4	0.44015 (5)	0.15038 (19)	0.44819 (12)	0.0191 (3)
C5	0.40794 (6)	0.0750 (2)	0.36146 (12)	0.0242 (3)
H5	0.4179	0.0661	0.2932	0.029*
C6	0.36121 (6)	0.0141 (2)	0.37817 (13)	0.0275 (4)
H6	0.3388	−0.0391	0.3207	0.033*
C7	0.34626 (6)	0.0292 (2)	0.47829 (13)	0.0273 (4)
H7	0.3136	−0.0118	0.4873	0.033*
C8	0.37807 (5)	0.1024 (2)	0.56412 (12)	0.0234 (3)
H8	0.3677	0.1117	0.6320	0.028*
C11	0.62782 (5)	0.49568 (19)	0.68791 (11)	0.0188 (3)
C12	0.67079 (5)	0.5438 (2)	0.64573 (12)	0.0200 (3)
H12	0.6734	0.5140	0.5740	0.024*
C13	0.70955 (5)	0.6348 (2)	0.70855 (12)	0.0213 (3)
C14	0.70650 (6)	0.6824 (2)	0.81238 (12)	0.0245 (3)
H14	0.7333	0.7463	0.8547	0.029*
C15	0.66341 (6)	0.6349 (2)	0.85358 (12)	0.0249 (3)
H15	0.6607	0.6672	0.9248	0.030*
C16	0.62434 (6)	0.5413 (2)	0.79260 (12)	0.0220 (3)
H16	0.5953	0.5083	0.8222	0.026*

	U11	U22	U33	U12	U13	U23
Cl1	0.0200 (2)	0.0423 (3)	0.0307 (2)	−0.00460 (15)	0.00835 (16)	0.00331 (17)
S1	0.0228 (2)	0.0232 (2)	0.0121 (2)	0.00280 (14)	0.00466 (14)	0.00001 (13)
O1	0.0263 (6)	0.0325 (6)	0.0148 (6)	−0.0019 (4)	0.0074 (4)	−0.0004 (4)
N1	0.0188 (6)	0.0221 (7)	0.0128 (6)	0.0014 (5)	0.0041 (5)	0.0011 (5)
C1	0.0199 (7)	0.0189 (7)	0.0161 (8)	0.0046 (5)	0.0061 (5)	0.0018 (5)
N2	0.0183 (6)	0.0227 (7)	0.0143 (6)	0.0024 (5)	0.0019 (5)	0.0000 (5)
C2	0.0207 (7)	0.0178 (7)	0.0121 (7)	0.0050 (5)	0.0040 (5)	0.0019 (5)
C3	0.0203 (7)	0.0188 (7)	0.0156 (7)	0.0042 (6)	0.0008 (5)	0.0014 (5)
C4	0.0220 (7)	0.0184 (7)	0.0167 (7)	0.0044 (6)	0.0024 (6)	0.0011 (6)
C5	0.0322 (8)	0.0214 (8)	0.0172 (8)	0.0050 (6)	−0.0009 (6)	−0.0020 (6)
C6	0.0301 (8)	0.0230 (8)	0.0256 (9)	0.0001 (6)	−0.0060 (6)	−0.0029 (6)
C7	0.0233 (8)	0.0253 (9)	0.0311 (9)	−0.0005 (6)	−0.0015 (6)	0.0036 (7)
C8	0.0225 (7)	0.0260 (9)	0.0215 (8)	0.0026 (6)	0.0030 (6)	0.0032 (6)
C11	0.0220 (7)	0.0182 (7)	0.0170 (7)	0.0033 (6)	0.0053 (6)	0.0021 (6)
C12	0.0220 (7)	0.0228 (8)	0.0162 (7)	0.0034 (6)	0.0061 (6)	0.0008 (6)
C13	0.0198 (7)	0.0231 (8)	0.0221 (8)	0.0012 (6)	0.0067 (6)	0.0048 (6)
C14	0.0280 (8)	0.0240 (8)	0.0202 (8)	−0.0027 (6)	0.0004 (6)	0.0010 (6)
C15	0.0337 (8)	0.0259 (8)	0.0159 (7)	−0.0028 (7)	0.0063 (6)	0.0000 (6)
C16	0.0267 (8)	0.0241 (8)	0.0173 (8)	−0.0004 (6)	0.0095 (6)	0.0027 (6)

Cl1—C13	1.7386 (15)	C6—C7	1.397 (2)
S1—C4	1.7360 (15)	C6—H6	0.9500
S1—C2	1.7459 (14)	C7—C8	1.378 (2)
O1—C1	1.2216 (18)	C7—H7	0.9500
N1—C1	1.3696 (18)	C8—H8	0.9500
N1—C2	1.3794 (18)	C11—C16	1.389 (2)
N1—H1	0.94 (2)	C11—C12	1.392 (2)
C1—C11	1.491 (2)	C12—C13	1.378 (2)
N2—C2	1.3008 (19)	C12—H12	0.9500
N2—C3	1.3912 (18)	C13—C14	1.380 (2)
C3—C8	1.395 (2)	C14—C15	1.388 (2)
C3—C4	1.400 (2)	C14—H14	0.9500
C4—C5	1.397 (2)	C15—C16	1.383 (2)
C5—C6	1.378 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C4—S1—C2	88.03 (7)	C8—C7—H7	119.4
C1—N1—C2	122.53 (12)	C6—C7—H7	119.4
C1—N1—H1	125.0 (11)	C7—C8—C3	118.64 (14)
C2—N1—H1	111.8 (11)	C7—C8—H8	120.7
O1—C1—N1	120.63 (13)	C3—C8—H8	120.7
O1—C1—C11	121.46 (13)	C16—C11—C12	119.59 (14)
N1—C1—C11	117.86 (12)	C16—C11—C1	124.15 (13)
C2—N2—C3	109.98 (12)	C12—C11—C1	116.03 (12)
N2—C2—N1	120.53 (13)	C13—C12—C11	119.64 (13)
N2—C2—S1	117.01 (11)	C13—C12—H12	120.2
N1—C2—S1	122.45 (11)	C11—C12—H12	120.2
N2—C3—C8	125.53 (13)	C12—C13—C14	121.49 (14)
N2—C3—C4	114.62 (13)	C12—C13—Cl1	118.93 (12)
C8—C3—C4	119.85 (14)	C14—C13—Cl1	119.52 (12)
C5—C4—C3	121.38 (14)	C13—C14—C15	118.48 (14)
C5—C4—S1	128.30 (12)	C13—C14—H14	120.8
C3—C4—S1	110.32 (11)	C15—C14—H14	120.8
C6—C5—C4	117.87 (15)	C16—C15—C14	121.08 (14)
C6—C5—H5	121.1	C16—C15—H15	119.5
C4—C5—H5	121.1	C14—C15—H15	119.5
C5—C6—C7	121.06 (14)	C15—C16—C11	119.71 (13)
C5—C6—H6	119.5	C15—C16—H16	120.1
C7—C6—H6	119.5	C11—C16—H16	120.1
C8—C7—C6	121.19 (15)
C2—N1—C1—O1	−2.6 (2)	C5—C6—C7—C8	−1.2 (2)
C2—N1—C1—C11	174.90 (12)	C6—C7—C8—C3	0.3 (2)
C3—N2—C2—N1	−177.62 (12)	N2—C3—C8—C7	−178.45 (14)
C3—N2—C2—S1	1.43 (16)	C4—C3—C8—C7	0.9 (2)
C1—N1—C2—N2	−171.57 (13)	O1—C1—C11—C16	165.51 (14)
C1—N1—C2—S1	9.43 (19)	N1—C1—C11—C16	−11.9 (2)
C4—S1—C2—N2	−1.80 (12)	O1—C1—C11—C12	−8.9 (2)
C4—S1—C2—N1	177.23 (12)	N1—C1—C11—C12	173.61 (12)
C2—N2—C3—C8	179.29 (14)	C16—C11—C12—C13	0.5 (2)
C2—N2—C3—C4	−0.12 (18)	C1—C11—C12—C13	175.22 (13)
N2—C3—C4—C5	178.08 (13)	C11—C12—C13—C14	−1.1 (2)
C8—C3—C4—C5	−1.4 (2)	C11—C12—C13—Cl1	−178.45 (11)
N2—C3—C4—S1	−1.19 (16)	C12—C13—C14—C15	0.7 (2)
C8—C3—C4—S1	179.37 (11)	Cl1—C13—C14—C15	178.04 (12)
C2—S1—C4—C5	−177.64 (15)	C13—C14—C15—C16	0.3 (2)
C2—S1—C4—C3	1.56 (11)	C14—C15—C16—C11	−0.8 (2)
C3—C4—C5—C6	0.5 (2)	C12—C11—C16—C15	0.4 (2)
S1—C4—C5—C6	179.62 (12)	C1—C11—C16—C15	−173.83 (14)
C4—C5—C6—C7	0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.94 (2)	2.02 (2)	2.9429 (18)	168.9 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.94 (2)	2.02 (2)	2.9429 (18)	168.9 (17)

Symmetry code: (i) .