Crystal structure of 1-[(2,2-dimethyl-1,3-dioxolan-4-yl)meth-yl]-2-(thia-zol-4-yl)-1H-benzimidazole.

The benzimidazole ring in the title compound, C16H17N3O2S, is almost planar, with the greatest deviation from the mean plane being 0.032 (1) Å. The fused-ring system makes dihedral angles of 19.91 (7) and 24.51 (8)° with the best plane through each of the thia-zol-4-yl and 1,3-dioxolan-4-yl rings, respectively; the latter exhibits an envelope conformation with the methyl-ene C atom being the flap. Finally, the thia-zol-4-yl ring makes a dihedral angle of 33.85 (9)° with the 1,3-dioxolan-4-yl ring. In the crystal, mol-ecules are connected by a pair of C-H⋯π(imidazole) inter-actions to form centrosymmetric aggregates.

Related literature

For the use of the title compound as an anthelmintic, see: Brown et al. (1961 ▸); Hennekeuser et al. (1969 ▸); as a food preservative and an agricultural fungicide, see: Arenas & Johnson (1994 ▸); for induction of aneuploidy and photogenotoxicity in bacteria and cultured human cells, see: Watanabe-Akanuma et al. (2005 ▸); as an anti-angiogenic, see: Cha et al. (2012 ▸); and as a ligand for transition metal ions, see: Gueddar et al. (2013 ▸).

Experimental

Crystal data

C16H17N3O2S

M = 315.38

Triclinic,

a = 9.3177 (5) Å

b = 9.3786 (6) Å

c = 9.5418 (6) Å

α = 78.739 (4)°

β = 78.777 (3)°

γ = 73.632 (3)°

V = 775.95 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.36 × 0.31 × 0.26 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.700, T max = 0.747

19810 measured reflections

4740 independent reflections

2804 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.116

S = 1.03

4740 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT-Plus (Bruker, 2009 ▸); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS2014/ (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip,2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S205698901502085X/tk5404sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901502085X/tk5404Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901502085X/tk5404Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901502085X/tk5404fig1.tif

Mol­ecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

CCDC reference: 1435046

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H17N3O2S	Z = 2
Mr = 315.38	F(000) = 332
Triclinic, P1	Dx = 1.350 Mg m−3
a = 9.3177 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3786 (6) Å	Cell parameters from 4740 reflections
c = 9.5418 (6) Å	θ = 2.8–30.5°
α = 78.739 (4)°	µ = 0.22 mm−1
β = 78.777 (3)°	T = 296 K
γ = 73.632 (3)°	Block, colourless
V = 775.95 (8) Å3	0.36 × 0.31 × 0.26 mm

Bruker X8 APEX diffractometer	4740 independent reflections
Radiation source: fine-focus sealed tube	2804 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 30.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.700, Tmax = 0.747	k = −13→13
19810 measured reflections	l = −13→13

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.0871P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4740 reflections	Δρmax = 0.16 e Å−3
199 parameters	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.9210 (2)	−0.0317 (2)	0.68651 (19)	0.0621 (5)
H1	1.0193	−0.0386	0.6391	0.074*
C2	0.69556 (19)	−0.05253 (19)	0.84926 (17)	0.0567 (4)
H2	0.6188	−0.0714	0.9230	0.068*
C3	0.67345 (17)	0.04071 (16)	0.72279 (15)	0.0455 (3)
C4	0.52432 (17)	0.11882 (16)	0.68306 (15)	0.0431 (3)
C5	0.28330 (18)	0.20058 (17)	0.69744 (17)	0.0480 (4)
C6	0.12767 (19)	0.2376 (2)	0.7404 (2)	0.0625 (5)
H6	0.0870	0.2227	0.8375	0.075*
C7	0.0354 (2)	0.2967 (2)	0.6362 (2)	0.0700 (5)
H7	−0.0690	0.3218	0.6636	0.084*
C8	0.0949 (2)	0.3197 (2)	0.4904 (2)	0.0672 (5)
H8	0.0292	0.3598	0.4225	0.081*
C9	0.2485 (2)	0.28454 (19)	0.44413 (19)	0.0569 (4)
H9	0.2883	0.2997	0.3467	0.068*
C10	0.34127 (17)	0.22519 (16)	0.55071 (16)	0.0450 (3)
C11	0.60240 (18)	0.16781 (16)	0.40757 (15)	0.0454 (3)
H11A	0.5501	0.1612	0.3315	0.055*
H11B	0.6843	0.0776	0.4179	0.055*
C12	0.66868 (18)	0.30373 (17)	0.36290 (16)	0.0477 (4)
H12	0.7195	0.3150	0.4394	0.057*
C13	0.55626 (19)	0.44806 (18)	0.31814 (17)	0.0535 (4)
H13A	0.4595	0.4562	0.3802	0.064*
H13B	0.5932	0.5348	0.3188	0.064*
C14	0.69603 (17)	0.36581 (17)	0.11179 (16)	0.0488 (4)
C15	0.6876 (2)	0.2593 (2)	0.01678 (19)	0.0673 (5)
H15A	0.7877	0.2135	−0.0270	0.101*
H15B	0.6277	0.3134	−0.0572	0.101*
H15C	0.6420	0.1827	0.0738	0.101*
C16	0.7744 (2)	0.4856 (2)	0.0327 (2)	0.0702 (5)
H16A	0.8749	0.4389	−0.0094	0.105*
H16B	0.7793	0.5480	0.0993	0.105*
H16C	0.7187	0.5459	−0.0422	0.105*
N1	0.80427 (15)	0.05273 (16)	0.62983 (15)	0.0575 (4)
N2	0.40020 (14)	0.13467 (15)	0.77840 (13)	0.0487 (3)
N3	0.49717 (14)	0.17320 (13)	0.54286 (12)	0.0428 (3)
O1	0.77265 (12)	0.28446 (12)	0.23223 (11)	0.0532 (3)
O2	0.54583 (12)	0.43257 (12)	0.17557 (11)	0.0528 (3)
S1	0.88238 (5)	−0.12939 (6)	0.85352 (5)	0.06612 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0568 (10)	0.0661 (12)	0.0570 (10)	−0.0168 (9)	−0.0043 (8)	0.0032 (9)
C2	0.0634 (10)	0.0589 (10)	0.0394 (8)	−0.0103 (8)	−0.0008 (7)	−0.0019 (7)
C3	0.0575 (9)	0.0398 (8)	0.0378 (8)	−0.0142 (7)	−0.0019 (7)	−0.0050 (6)
C4	0.0582 (9)	0.0353 (7)	0.0353 (7)	−0.0151 (6)	−0.0030 (6)	−0.0028 (6)
C5	0.0571 (9)	0.0408 (8)	0.0460 (8)	−0.0155 (7)	−0.0027 (7)	−0.0067 (7)
C6	0.0574 (10)	0.0646 (11)	0.0609 (11)	−0.0161 (8)	0.0029 (8)	−0.0092 (9)
C7	0.0560 (10)	0.0694 (13)	0.0828 (14)	−0.0143 (9)	−0.0089 (10)	−0.0110 (11)
C8	0.0697 (12)	0.0584 (11)	0.0753 (13)	−0.0103 (9)	−0.0268 (10)	−0.0070 (9)
C9	0.0713 (11)	0.0475 (9)	0.0522 (10)	−0.0137 (8)	−0.0138 (8)	−0.0055 (7)
C10	0.0560 (9)	0.0344 (7)	0.0455 (8)	−0.0143 (6)	−0.0063 (7)	−0.0053 (6)
C11	0.0600 (9)	0.0392 (8)	0.0350 (7)	−0.0138 (7)	−0.0013 (6)	−0.0045 (6)
C12	0.0630 (9)	0.0460 (9)	0.0358 (7)	−0.0202 (7)	−0.0048 (7)	−0.0032 (6)
C13	0.0705 (10)	0.0408 (8)	0.0465 (9)	−0.0163 (8)	0.0016 (8)	−0.0071 (7)
C14	0.0540 (9)	0.0481 (9)	0.0383 (8)	−0.0113 (7)	−0.0030 (7)	0.0013 (7)
C15	0.0823 (13)	0.0676 (12)	0.0505 (10)	−0.0155 (10)	−0.0057 (9)	−0.0144 (9)
C16	0.0817 (13)	0.0655 (12)	0.0573 (11)	−0.0289 (10)	0.0011 (9)	0.0091 (9)
N1	0.0523 (8)	0.0596 (9)	0.0537 (8)	−0.0172 (7)	−0.0055 (6)	0.0095 (7)
N2	0.0546 (7)	0.0489 (7)	0.0405 (7)	−0.0155 (6)	−0.0004 (6)	−0.0048 (6)
N3	0.0534 (7)	0.0380 (7)	0.0354 (6)	−0.0131 (5)	−0.0029 (5)	−0.0029 (5)
O1	0.0508 (6)	0.0579 (7)	0.0422 (6)	−0.0102 (5)	−0.0041 (5)	0.0049 (5)
O2	0.0562 (6)	0.0514 (6)	0.0429 (6)	−0.0066 (5)	−0.0048 (5)	−0.0014 (5)
S1	0.0670 (3)	0.0732 (3)	0.0465 (3)	−0.0051 (2)	−0.0116 (2)	0.0032 (2)

C1—N1	1.295 (2)	C10—N3	1.3879 (19)
C1—S1	1.7030 (18)	C11—N3	1.4612 (18)
C1—H1	0.9300	C11—C12	1.522 (2)
C2—C3	1.359 (2)	C11—H11A	0.9700
C2—S1	1.6913 (18)	C11—H11B	0.9700
C2—H2	0.9300	C12—O1	1.4300 (17)
C3—N1	1.3794 (19)	C12—C13	1.504 (2)
C3—C4	1.461 (2)	C12—H12	0.9800
C4—N2	1.3167 (18)	C13—O2	1.4205 (19)
C4—N3	1.3807 (18)	C13—H13A	0.9700
C5—N2	1.388 (2)	C13—H13B	0.9700
C5—C6	1.390 (2)	C14—O2	1.4299 (18)
C5—C10	1.398 (2)	C14—O1	1.4431 (18)
C6—C7	1.372 (3)	C14—C15	1.501 (2)
C6—H6	0.9300	C14—C16	1.510 (2)
C7—C8	1.393 (3)	C15—H15A	0.9600
C7—H7	0.9300	C15—H15B	0.9600
C8—C9	1.378 (3)	C15—H15C	0.9600
C8—H8	0.9300	C16—H16A	0.9600
C9—C10	1.393 (2)	C16—H16B	0.9600
C9—H9	0.9300	C16—H16C	0.9600
N1—C1—S1	115.57 (13)	O1—C12—C11	108.49 (12)
N1—C1—H1	122.2	C13—C12—C11	114.15 (13)
S1—C1—H1	122.2	O1—C12—H12	110.6
C3—C2—S1	110.39 (12)	C13—C12—H12	110.6
C3—C2—H2	124.8	C11—C12—H12	110.6
S1—C2—H2	124.8	O2—C13—C12	101.61 (12)
C2—C3—N1	114.69 (14)	O2—C13—H13A	111.4
C2—C3—C4	123.77 (14)	C12—C13—H13A	111.4
N1—C3—C4	121.50 (13)	O2—C13—H13B	111.4
N2—C4—N3	113.24 (13)	C12—C13—H13B	111.4
N2—C4—C3	122.47 (13)	H13A—C13—H13B	109.3
N3—C4—C3	124.13 (13)	O2—C14—O1	104.86 (11)
N2—C5—C6	130.26 (15)	O2—C14—C15	108.45 (13)
N2—C5—C10	110.23 (13)	O1—C14—C15	110.33 (13)
C6—C5—C10	119.47 (16)	O2—C14—C16	110.57 (13)
C7—C6—C5	118.54 (17)	O1—C14—C16	109.05 (13)
C7—C6—H6	120.7	C15—C14—C16	113.24 (15)
C5—C6—H6	120.7	C14—C15—H15A	109.5
C6—C7—C8	121.29 (17)	C14—C15—H15B	109.5
C6—C7—H7	119.4	H15A—C15—H15B	109.5
C8—C7—H7	119.4	C14—C15—H15C	109.5
C9—C8—C7	121.69 (18)	H15A—C15—H15C	109.5
C9—C8—H8	119.2	H15B—C15—H15C	109.5
C7—C8—H8	119.2	C14—C16—H16A	109.5
C8—C9—C10	116.57 (17)	C14—C16—H16B	109.5
C8—C9—H9	121.7	H16A—C16—H16B	109.5
C10—C9—H9	121.7	C14—C16—H16C	109.5
N3—C10—C9	131.86 (14)	H16A—C16—H16C	109.5
N3—C10—C5	105.65 (13)	H16B—C16—H16C	109.5
C9—C10—C5	122.43 (15)	C1—N1—C3	109.91 (14)
N3—C11—C12	113.34 (12)	C4—N2—C5	104.91 (12)
N3—C11—H11A	108.9	C4—N3—C10	105.96 (12)
C12—C11—H11A	108.9	C4—N3—C11	129.77 (13)
N3—C11—H11B	108.9	C10—N3—C11	124.02 (12)
C12—C11—H11B	108.9	C12—O1—C14	108.64 (11)
H11A—C11—H11B	107.7	C13—O2—C14	106.22 (12)
O1—C12—C13	101.94 (12)	C2—S1—C1	89.43 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···Cg1i	0.97	2.83	3.7543 (18)	160

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N2/N3/C4/C5/C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯Cg1i	0.97	2.83	3.7543 (18)	160

Symmetry code: (i) .