4-(1H-Benzimidazol-2-ylmeth-yl)-2H-1,4-benzothia-zin-3(4H)-one.

In the title compound, C(16)H(13)N(3)OS, the thio-morpholine ring exists in a screw boat conformation. The angle between the benzimidazole ring system and the benzene ring fused to the thia-zine ring is 67.22 (6)°. In the crystal, mol-ecules form infinite chains along the a axis via inter-molecular N-H⋯N inter-actions. C-H⋯π inter-actions also contribute to the stability of the crystal structure.

Related literature

For the biological activity of mol­ecules containing 1H-benzimidazole, see: Sridhar & Ramesh (2001 ▶); Guven et al. (2007 ▶); Nofal et al. (2002 ▶); Pedini et al. (1994 ▶). For a related structure, see: Fun et al. (2009 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H13N3OS

M = 295.35

Orthorhombic,

a = 9.4498 (8) Å

b = 17.0223 (16) Å

c = 17.4454 (16) Å

V = 2806.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.50 × 0.20 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.893, T max = 0.969

16727 measured reflections

4075 independent reflections

3185 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.03

4075 reflections

194 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019367/wn2387sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019367/wn2387Isup2.hkl

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

C16H13N3OS	F(000) = 1232
Mr = 295.35	Dx = 1.398 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4703 reflections
a = 9.4498 (8) Å	θ = 2.4–31.6°
b = 17.0223 (16) Å	µ = 0.23 mm−1
c = 17.4454 (16) Å	T = 100 K
V = 2806.2 (4) Å3	Block, red
Z = 8	0.50 × 0.20 × 0.13 mm

Bruker APEXII DUO CCD area-detector diffractometer	4075 independent reflections
Radiation source: fine-focus sealed tube	3185 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.893, Tmax = 0.969	k = −23→23
16727 measured reflections	l = −24→21

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) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0605P)2 + 1.2202P] where P = (Fo2 + 2Fc2)/3
4075 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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 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
S1	0.69098 (4)	0.04490 (2)	0.49857 (2)	0.02567 (12)
O1	0.90053 (12)	−0.12536 (7)	0.41611 (7)	0.0283 (2)
N1	1.05774 (11)	−0.12424 (7)	0.21967 (7)	0.0169 (2)
N2	0.82471 (11)	−0.10176 (7)	0.21708 (7)	0.0166 (2)
N3	0.84628 (12)	−0.01064 (7)	0.35843 (7)	0.0180 (2)
C1	0.75457 (14)	0.05425 (8)	0.34596 (8)	0.0177 (3)
C2	0.74342 (15)	0.08809 (8)	0.27346 (8)	0.0210 (3)
H2A	0.7935	0.0668	0.2325	0.025*
C3	0.65796 (16)	0.15354 (9)	0.26189 (9)	0.0251 (3)
H3A	0.6530	0.1764	0.2135	0.030*
C4	0.58032 (16)	0.18488 (9)	0.32169 (10)	0.0275 (3)
H4A	0.5232	0.2286	0.3137	0.033*
C5	0.58816 (16)	0.15078 (9)	0.39359 (10)	0.0256 (3)
H5A	0.5346	0.1711	0.4337	0.031*
C6	0.67593 (15)	0.08616 (8)	0.40635 (8)	0.0206 (3)
C7	0.70051 (17)	−0.05535 (9)	0.46596 (9)	0.0261 (3)
H7A	0.7100	−0.0900	0.5098	0.031*
H7B	0.6134	−0.0688	0.4396	0.031*
C8	0.82425 (15)	−0.06773 (8)	0.41241 (8)	0.0209 (3)
C9	0.96991 (14)	−0.02207 (8)	0.30913 (8)	0.0191 (3)
H9A	1.0499	−0.0374	0.3406	0.023*
H9B	0.9933	0.0274	0.2847	0.023*
C10	0.94729 (13)	−0.08304 (8)	0.24863 (8)	0.0159 (2)
C11	1.00375 (13)	−0.17492 (8)	0.16502 (8)	0.0165 (3)
C12	1.06703 (15)	−0.23109 (9)	0.11796 (8)	0.0213 (3)
H12A	1.1636	−0.2415	0.1201	0.026*
C13	0.97847 (17)	−0.27045 (9)	0.06787 (9)	0.0245 (3)
H13A	1.0162	−0.3086	0.0356	0.029*
C14	0.83220 (16)	−0.25414 (9)	0.06449 (9)	0.0234 (3)
H14A	0.7765	−0.2809	0.0291	0.028*
C15	0.76917 (15)	−0.19954 (8)	0.11228 (8)	0.0198 (3)
H15A	0.6724	−0.1898	0.1105	0.024*
C16	0.85770 (13)	−0.15965 (8)	0.16350 (8)	0.0158 (2)
H1N1	1.143 (2)	−0.1173 (12)	0.2353 (12)	0.033 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.0341 (2)	0.02221 (19)	0.02070 (19)	−0.00054 (14)	0.00590 (14)	−0.00461 (13)
O1	0.0333 (6)	0.0235 (5)	0.0283 (6)	0.0070 (4)	0.0003 (5)	0.0023 (4)
N1	0.0100 (5)	0.0214 (6)	0.0192 (5)	−0.0003 (4)	−0.0003 (4)	−0.0010 (4)
N2	0.0117 (5)	0.0174 (5)	0.0208 (6)	−0.0010 (4)	0.0004 (4)	−0.0003 (4)
N3	0.0166 (5)	0.0180 (5)	0.0194 (6)	0.0007 (4)	0.0020 (4)	−0.0006 (4)
C1	0.0157 (6)	0.0154 (6)	0.0221 (6)	−0.0018 (4)	0.0004 (5)	−0.0017 (5)
C2	0.0220 (6)	0.0180 (6)	0.0230 (7)	−0.0014 (5)	0.0003 (5)	−0.0005 (5)
C3	0.0282 (7)	0.0192 (7)	0.0279 (8)	−0.0014 (5)	−0.0046 (6)	0.0018 (6)
C4	0.0238 (7)	0.0185 (6)	0.0402 (9)	0.0032 (5)	−0.0036 (6)	−0.0013 (6)
C5	0.0220 (7)	0.0214 (7)	0.0334 (8)	0.0014 (5)	0.0045 (6)	−0.0069 (6)
C6	0.0201 (6)	0.0187 (6)	0.0230 (7)	−0.0025 (5)	0.0021 (5)	−0.0039 (5)
C7	0.0349 (8)	0.0197 (7)	0.0236 (7)	−0.0006 (6)	0.0088 (6)	−0.0004 (6)
C8	0.0247 (7)	0.0187 (6)	0.0192 (7)	−0.0005 (5)	−0.0001 (5)	−0.0014 (5)
C9	0.0133 (5)	0.0209 (6)	0.0232 (7)	−0.0019 (5)	0.0004 (5)	−0.0036 (5)
C10	0.0116 (5)	0.0173 (6)	0.0188 (6)	−0.0007 (4)	0.0018 (5)	0.0013 (5)
C11	0.0138 (5)	0.0191 (6)	0.0167 (6)	−0.0002 (4)	0.0006 (5)	0.0011 (5)
C12	0.0182 (6)	0.0245 (7)	0.0211 (7)	0.0030 (5)	0.0035 (5)	−0.0009 (5)
C13	0.0293 (7)	0.0238 (7)	0.0204 (7)	0.0013 (6)	0.0038 (6)	−0.0042 (5)
C14	0.0256 (7)	0.0241 (7)	0.0204 (7)	−0.0036 (5)	−0.0026 (5)	−0.0012 (5)
C15	0.0171 (6)	0.0214 (6)	0.0211 (7)	−0.0029 (5)	−0.0027 (5)	0.0019 (5)
C16	0.0134 (5)	0.0171 (6)	0.0168 (6)	−0.0011 (4)	0.0003 (5)	0.0030 (5)

S1—C6	1.7611 (16)	C5—C6	1.396 (2)
S1—C7	1.8011 (16)	C5—H5A	0.9300
O1—C8	1.2191 (18)	C7—C8	1.511 (2)
N1—C10	1.3552 (16)	C7—H7A	0.9700
N1—C11	1.3831 (17)	C7—H7B	0.9700
N1—H1N1	0.86 (2)	C9—C10	1.4955 (19)
N2—C10	1.3214 (16)	C9—H9A	0.9700
N2—C16	1.3936 (17)	C9—H9B	0.9700
N3—C8	1.3692 (19)	C11—C12	1.3950 (19)
N3—C1	1.4207 (17)	C11—C16	1.4046 (18)
N3—C9	1.4637 (17)	C12—C13	1.383 (2)
C1—C2	1.394 (2)	C12—H12A	0.9300
C1—C6	1.3990 (19)	C13—C14	1.411 (2)
C2—C3	1.391 (2)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.383 (2)
C3—C4	1.382 (2)	C14—H14A	0.9300
C3—H3A	0.9300	C15—C16	1.3998 (19)
C4—C5	1.384 (2)	C15—H15A	0.9300
C4—H4A	0.9300
C6—S1—C7	95.35 (7)	H7A—C7—H7B	108.0
C10—N1—C11	107.20 (11)	O1—C8—N3	121.18 (13)
C10—N1—H1N1	122.3 (14)	O1—C8—C7	122.47 (14)
C11—N1—H1N1	130.5 (14)	N3—C8—C7	116.35 (12)
C10—N2—C16	104.70 (11)	N3—C9—C10	113.14 (11)
C8—N3—C1	124.36 (12)	N3—C9—H9A	109.0
C8—N3—C9	115.55 (12)	C10—C9—H9A	109.0
C1—N3—C9	120.02 (11)	N3—C9—H9B	109.0
C2—C1—C6	118.86 (13)	C10—C9—H9B	109.0
C2—C1—N3	120.42 (12)	H9A—C9—H9B	107.8
C6—C1—N3	120.71 (13)	N2—C10—N1	113.27 (12)
C3—C2—C1	120.45 (14)	N2—C10—C9	125.91 (12)
C3—C2—H2A	119.8	N1—C10—C9	120.81 (11)
C1—C2—H2A	119.8	N1—C11—C12	132.45 (12)
C4—C3—C2	120.52 (15)	N1—C11—C16	105.08 (11)
C4—C3—H3A	119.7	C12—C11—C16	122.47 (13)
C2—C3—H3A	119.7	C13—C12—C11	116.39 (13)
C3—C4—C5	119.58 (14)	C13—C12—H12A	121.8
C3—C4—H4A	120.2	C11—C12—H12A	121.8
C5—C4—H4A	120.2	C12—C13—C14	121.59 (13)
C4—C5—C6	120.46 (14)	C12—C13—H13A	119.2
C4—C5—H5A	119.8	C14—C13—H13A	119.2
C6—C5—H5A	119.8	C15—C14—C13	121.92 (14)
C5—C6—C1	120.11 (14)	C15—C14—H14A	119.0
C5—C6—S1	120.53 (11)	C13—C14—H14A	119.0
C1—C6—S1	119.35 (11)	C14—C15—C16	116.96 (13)
C8—C7—S1	111.46 (10)	C14—C15—H15A	121.5
C8—C7—H7A	109.3	C16—C15—H15A	121.5
S1—C7—H7A	109.3	N2—C16—C15	129.61 (12)
C8—C7—H7B	109.3	N2—C16—C11	109.75 (11)
S1—C7—H7B	109.3	C15—C16—C11	120.64 (13)
C8—N3—C1—C2	−150.61 (14)	C8—N3—C9—C10	76.17 (15)
C9—N3—C1—C2	25.96 (19)	C1—N3—C9—C10	−100.69 (14)
C8—N3—C1—C6	30.5 (2)	C16—N2—C10—N1	0.06 (15)
C9—N3—C1—C6	−152.88 (13)	C16—N2—C10—C9	178.82 (13)
C6—C1—C2—C3	1.4 (2)	C11—N1—C10—N2	−0.62 (16)
N3—C1—C2—C3	−177.44 (13)	C11—N1—C10—C9	−179.45 (12)
C1—C2—C3—C4	−1.5 (2)	N3—C9—C10—N2	28.7 (2)
C2—C3—C4—C5	0.1 (2)	N3—C9—C10—N1	−152.62 (12)
C3—C4—C5—C6	1.3 (2)	C10—N1—C11—C12	−179.20 (15)
C4—C5—C6—C1	−1.4 (2)	C10—N1—C11—C16	0.88 (14)
C4—C5—C6—S1	177.68 (12)	N1—C11—C12—C13	−178.56 (14)
C2—C1—C6—C5	0.0 (2)	C16—C11—C12—C13	1.3 (2)
N3—C1—C6—C5	178.85 (13)	C11—C12—C13—C14	0.3 (2)
C2—C1—C6—S1	−179.06 (10)	C12—C13—C14—C15	−1.7 (2)
N3—C1—C6—S1	−0.20 (18)	C13—C14—C15—C16	1.3 (2)
C7—S1—C6—C5	142.33 (13)	C10—N2—C16—C15	−178.42 (14)
C7—S1—C6—C1	−38.62 (13)	C10—N2—C16—C11	0.52 (15)
C6—S1—C7—C8	58.75 (12)	C14—C15—C16—N2	179.23 (13)
C1—N3—C8—O1	173.88 (13)	C14—C15—C16—C11	0.4 (2)
C9—N3—C8—O1	−2.8 (2)	N1—C11—C16—N2	−0.88 (15)
C1—N3—C8—C7	−5.6 (2)	C12—C11—C16—N2	179.20 (12)
C9—N3—C8—C7	177.65 (12)	N1—C11—C16—C15	178.18 (12)
S1—C7—C8—O1	137.50 (14)	C12—C11—C16—C15	−1.8 (2)
S1—C7—C8—N3	−42.98 (17)

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2i	0.859 (19)	1.926 (19)	2.7800 (15)	173 (2)
C12—H12A···Cg1ii	0.93	2.97	3.6736 (16)	134
C3—H3A···Cg2iii	0.93	2.61	3.4750 (17)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2i	0.859 (19)	1.926 (19)	2.7800 (15)	173 (2)
C12—H12A⋯Cg1ii	0.93	2.97	3.6736 (16)	134
C3—H3A⋯Cg2iii	0.93	2.61	3.4750 (17)	155

Symmetry codes: (i) ; (ii) ; (iii) .