Crystal structure of 5-[2-(9H-carbazol-9-yl)eth­yl]-1,3,4-oxa­diazole-2(3H)-thione

Simpson, J.; Mohamed, S.K.; El-Emary, T.I.; Albayati, M.R.

doi:10.1107/S2056989017009252

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ISSN: 2056-9890

Volume 73| Part 7| July 2017| Pages 1066-1069

https://doi.org/10.1107/S2056989017009252

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Crystal structure of 5-[2-(9H-carbazol-9-yl)ethyl]-1,3,4-oxadiazole-2(3H)-thione

Jim Simpson,^a Shaaban K. Mohamed,^b,^c Talaat I. El-Emary ^d and Mustafa R. Albayati ^e ^*

^aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Chemistry, Faculty of Science, Assiut University, 71515 Assiut, Egypt, and ^eKirkuk University, College of Education, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by J. T. Mague, Tulane University, USA (Received 16 May 2017; accepted 20 June 2017; online 23 June 2017)

The title compound, C₁₆H₁₃N₃OS, comprises an oxadiazolethione ring bound to the N atom of an almost planar carbazole ring system (r.m.s. deviation = 0.0088 Å) through an ethylene chain. The oxadiazole ring is inclined to the the carbazole ring system by 40.71 (6)°. In the crystal, N—H⋯O, N—H⋯S, C—H⋯N and C—H⋯S hydrogen bonds combine with C—H⋯π(ring) and π–π contacts to stack the molecules along the b-axis direction.

Keywords: crystal structure; carbazole; oxadiazolethione; hydrogen bonds; C—H⋯π(ring) contacts; π–π stacking.

CCDC reference: 1557216

1. Chemical context

Carbazole derivatives have been shown to have several industrial applications including use in optoelectronic devices (Fitilis et al., 2007 ; Peng et al., 2011 ), dye-sensitized solar cells (Li et al., 2010 ) and photochromic dyes (Billah et al., 2008 ). Moreover, fused heterocycles with carbazole scaffolds are noted for their biological activities. They are found in drugs such as tubingensin A and B and have been shown to have both antiviral and cytotoxic activities (TePaske et al., 1989 ). The anti-inflammatory agents caprofen and etodolaca and the antipyretic agent nincazole (Ghoneim et al., 2006 ) are also carbazole based. The biological activity of so many carbazole-based heterocycles encouraged us to synthesize the title compound and its molecular crystal structure is reported here.

2. Structural commentary

In the title compound C₁₆H₁₃N₃OS, (I), the oxadiazolethione ring binds to the carbazole ring system through a C2–C3–C4–N3 ethylene chain with the ring systems inclined at an angle of 40.71 (6)°, Fig. 1. The carbazole ring system is almost planar with the outer C5–C10 and C11–C16 benzene rings subtending angles of 0.38 (13) and 0.64 (13)°, respectively, to the central N3/C5/C10/C11/C16 ring. Bond lengths and angles in both ring systems are normal and similar to those found in the numerous other carbazole structures (see, for example, Kimura et al., 1985 ) and those of the few known oxadiazolethione derivatives with alkane chains at C5 (Khan et al. 2014 ; Zheng et al. 2006 ).

Figure 1
The molecular structure of (I)

with ellipsoids drawn at the 50% probability level.

3. Supramolecular features

In the crystal, classical N1—H1N⋯O1 and N1—H1N⋯S1 hydrogen bonds form C(4) chains of molecules linked in a head-to-head fashion along the b-axis direction, Fig. 2. These contacts are bolstered by the C4 atom acting as a bifurcated donor forming weaker C4—H4A⋯N2 hydrogen bonds and C4—H4B⋯Cg4 interactions, Table 1. In the chains, the mean plane of the oxadiazole ring is inclined at 10.7° to (101). The N—H⋯O and N—H⋯S hydrogen bonds also impose close O1⋯N2(x, y − 1, z) contacts of 2.9516 (18) Å. Adjacent chains are further linked by C3—H3B⋯S1 hydrogen bonds that form inversion dimers, enclosing R₂²(12) rings. This combination of contacts stacks molecules along the b-axis direction, Fig. 3. Adjacent oxadiazole rings form dimers through Cg1⋯Cg1^vi π–π contacts with centroid-to-centroid separations of 3.3931 (9) Å Cg1 is the centroid of the O1/C2/N3/N4/C5 ring; symmetry code: (vi) 1 − x, 1 − y, 1 − z]. These dimers are linked by much weaker C12—H12⋯Cg4 interactions, Table 1, forming chains along the ac diagonal, Fig. 4. This substantial array of contacts combines to form a three-dimensional network structure, Fig. 5.

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯S1ⁱ	0.89 (2)	2.75 (2)	3.6053 (14)	162.8 (19)
N1—H1N⋯O1ⁱ	0.89 (2)	2.62 (2)	3.0707 (18)	112.5 (16)
C3—H3B⋯S1ⁱⁱ	0.99	2.93	3.9061 (16)	169
C4—H4A⋯N2ⁱⁱⁱ	0.99	2.67	3.495 (2)	141
C4—H4B⋯Cg4ⁱⁱⁱ	0.99	2.87	3.4577 (17)	119
C12—H12⋯Cg4ⁱ	0.95	3.22	4.073 (2)	151
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+1; (iii) x, y-1, z.

Figure 2
Rows of molecules of (I)

along b. In this and subsequent figures, N—H⋯S (orange), N—H⋯O (dark blue) and C—H⋯N (light blue) hydrogen bonds are drawn as coloured dashed lines. C—H⋯π contacts are shown as green dotted lines with ring centroids displayed as coloured spheres.

Figure 3
Inversion dimers formed by C—H⋯S hydrogen bonds (dashed yellow lines) stacking rows of molecules of (I)

along b.

Figure 4
Chains of molecules of (I)

along the ac diagonal. Centroid–centroid contacts are drawn as green dotted lines.

Figure 5
Overall packing of (I)

viewed along the b-axis direction. Representative C—H⋯π hydrogen bonds and π–π contacts are shown as green dotted lines.

4. Database survey

Structures of carbazole derivatives abound in the Cambridge Structural Database (Version 5.38, November 2016 with one update; Groom et al., 2016 ) with 428 hits for solely organic molecules. Those with alkane chain substituents, at least two carbon atoms long on the pyrrole N atom, are less abundant with 47 hits for organic molecules alone. The simplest of these is N-ethyl carbazole itself (Kimura et al., 1985). This compound in fact appears in a number of manifestations as it seems to readily form co-crystals (Lee & Wallwork, 1978 ; Hosomi et al., 2000 ; Matsuoka et al., 1988 ; Zhu et al., 2014 ). No examples were found of oxadiazole rings at the end of the alkane chains; indeed, the only derivatives with simple five-membered rings in that position were dioxaborolane derivatives (Kalinin et al., 2003 ; Geier et al., 2009 ). In contrast, 1,3,4-oxadiazole-2-thiones are far less abundant with only 29 unique organic structures reported. Furthermore, crystal structures of compounds with a chain of two or more methylene units bound to the 5-carbon are rare, with only three such structures found: 5-[2-(2-methoxyphenyl)ethyl]-1,3,4-oxadiazole-2(3H)-thione and 5-[2-(4-methoxyphenyl)ethyl]-1,3,4-oxadiazole-2(3H)-thione (Khan et al. 2014) and 5-[3-(quinolin-8-yloxy)propyl]-1,3,4-oxadiazole-2(3H)-thione (Zheng et al. 2006)

5. Synthesis and crystallization

A mixture of 3-(9H-carbazol-9-yl)propanehydrazide (1.09 g, 4 mmol) and carbon disulfide (3 ml) in pyridine (15 mL) was heated under reflux on a water bath (333–343 K) overnight. The excess carbon disulfide was removed under reduced pressure and the reaction mixture was then poured into ice-cold water. The resulting precipitate was collected by filtration, washed with water, dried and recrystallized from mixed solvents of dioxane–water (1:1) to give (I) in 66% yield; m.p. 469–471 K. IR: NH, 3197, CH aromatic 3050, CH aliphatic 2940 cm⁻¹. ¹H NMR: δ (ppm) (DMSO-d₆) 2.35 (t, 2H, CH2), 4.12 (t, 2H, CH2), 7.35–8.38 (m, 8H, Ar-H), 9.95 (s, 1H, NH). ¹³C NMR (100 MHz, DMSO-d₆, DEPT) δ (ppm): 34.9, 51.4, 109.6, 119.9, 121.4, 122.8, 156.8, 188.9. ms: m/z 295 (M⁺) as molecular ion peak and base peak. Analysis calculated for C₁₆ H₁₃ N₃OS (295.4): C, 65.06; H, 4.44; N, 5.42. Found: C, 65.38; H, 4.65; N, 5.48.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The N-bound hydrogen atom was located in a difference-Fourier map and its coordinates refined with U_iso = 1.2U_eq (N). All H atoms bound to C were refined using a riding model with d(C—H) = 0.95 Å and U_iso(H) = 1.2U_eq(C) for aromatic, d(C—H) = 0.99 Å and U_iso(H) = 1.2U_eq(C) for CH₂ H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₃N₃OS
M_r	295.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	16.6868 (5), 4.9600 (1), 17.2353 (6)
β (°)	105.909 (3)
V (Å³)	1371.87 (7)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	2.11
Crystal size (mm)	0.27 × 0.15 × 0.09

Data collection
Diffractometer	Agilent SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.763, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11013, 2849, 2626
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.125, 1.06
No. of reflections	2849
No. of parameters	193
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.48
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), TITAN2000 (Hunter & Simpson, 1999 ), Mercury (Macrae et al., 2008 ), enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009 ), publCIF (Westrip, 2010 ) and WinGX (Farrugia, 2012 ).

Supporting information

CCDC reference: 1557216

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989017009252/mw2132sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017009252/mw2132Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989017009252/mw2132Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) and TITAN2000 (Hunter & Simpson, 1999); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), enCIFer (Allen et al., 2004), PLATON (Spek, 2009), publCIF (Westrip, 2010) and WinGX (Farrugia, 2012).

5-[2-(9H-carbazol-9-yl)ethyl]-1,3,4-oxadiazole-2(3H)-thione top

Crystal data top

C₁₆H₁₃N₃OS	F(000) = 616
M_r = 295.35	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 16.6868 (5) Å	Cell parameters from 7352 reflections
b = 4.9600 (1) Å	θ = 6.5–76.5°
c = 17.2353 (6) Å	µ = 2.11 mm⁻¹
β = 105.909 (3)°	T = 100 K
V = 1371.87 (7) Å³	Plate, colourless
Z = 4	0.27 × 0.15 × 0.09 mm

Data collection top

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	2849 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2626 reflections with I > 2σ(I)
Detector resolution: 5.1725 pixels mm^-1	R_int = 0.063
ω scans	θ_max = 76.5°, θ_min = 5.3°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	h = −20→20
T_min = 0.763, T_max = 1.000	k = −4→6
11013 measured reflections	l = −20→21

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.079P)² + 0.5548P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2849 reflections	Δρ_max = 0.43 e Å⁻³
193 parameters	Δρ_min = −0.48 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.55153 (7)	0.1963 (2)	0.58574 (7)	0.0155 (3)
C1	0.50674 (9)	0.3454 (3)	0.62638 (9)	0.0151 (3)
S1	0.43636 (2)	0.21061 (9)	0.66526 (2)	0.01955 (16)
N1	0.53275 (8)	0.5979 (3)	0.62294 (8)	0.0158 (3)
H1N	0.5152 (14)	0.740 (5)	0.6449 (14)	0.019*
N2	0.59279 (8)	0.6190 (3)	0.58088 (8)	0.0168 (3)
C2	0.60197 (9)	0.3745 (3)	0.56023 (9)	0.0146 (3)
C3	0.66006 (10)	0.2674 (3)	0.51646 (10)	0.0175 (3)
H6A	0.6797	0.4173	0.4885	0.021*
H3B	0.6301	0.1372	0.4751	0.021*
C4	0.73573 (9)	0.1269 (3)	0.57370 (10)	0.0168 (3)
H4A	0.7160	−0.0214	0.6022	0.020*
H4B	0.7707	0.0470	0.5416	0.020*
N3	0.78545 (8)	0.3109 (3)	0.63217 (8)	0.0151 (3)
C5	0.77515 (9)	0.3625 (3)	0.70793 (9)	0.0154 (3)
C6	0.72386 (10)	0.2314 (4)	0.74787 (10)	0.0201 (4)
H6	0.6892	0.0851	0.7237	0.024*
C7	0.72578 (11)	0.3239 (4)	0.82431 (11)	0.0273 (4)
H7	0.6917	0.2390	0.8531	0.033*
C8	0.77677 (13)	0.5393 (4)	0.85996 (10)	0.0309 (4)
H8	0.7763	0.5987	0.9122	0.037*
C9	0.82767 (11)	0.6669 (4)	0.82050 (11)	0.0262 (4)
H9	0.8621	0.8130	0.8452	0.031*
C10	0.82777 (9)	0.5777 (3)	0.74355 (10)	0.0182 (3)
C11	0.87157 (9)	0.6589 (3)	0.68573 (10)	0.0190 (3)
C12	0.93139 (10)	0.8561 (4)	0.68605 (12)	0.0274 (4)
H12	0.9509	0.9717	0.7312	0.033*
C13	0.96158 (11)	0.8797 (4)	0.61920 (13)	0.0327 (5)
H13	1.0023	1.0130	0.6188	0.039*
C14	0.93329 (11)	0.7113 (4)	0.55235 (13)	0.0296 (4)
H14	0.9556	0.7320	0.5076	0.036*
C15	0.87311 (10)	0.5133 (4)	0.54963 (11)	0.0223 (4)
H15	0.8535	0.3998	0.5040	0.027*
C16	0.84324 (9)	0.4908 (3)	0.61765 (10)	0.0167 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0145 (5)	0.0103 (5)	0.0207 (6)	−0.0003 (4)	0.0030 (4)	−0.0018 (4)
C1	0.0127 (7)	0.0132 (7)	0.0162 (7)	0.0011 (6)	−0.0014 (5)	−0.0011 (5)
S1	0.0185 (2)	0.0185 (3)	0.0215 (2)	−0.00502 (14)	0.00544 (16)	−0.00070 (14)
N1	0.0149 (6)	0.0108 (7)	0.0222 (6)	−0.0002 (5)	0.0057 (5)	−0.0018 (5)
N2	0.0139 (6)	0.0136 (7)	0.0230 (7)	−0.0003 (5)	0.0052 (5)	0.0000 (5)
C2	0.0116 (6)	0.0129 (7)	0.0166 (7)	−0.0004 (6)	−0.0006 (5)	0.0005 (6)
C3	0.0155 (7)	0.0185 (8)	0.0173 (7)	0.0004 (6)	0.0023 (6)	−0.0030 (6)
C4	0.0136 (7)	0.0144 (7)	0.0217 (7)	0.0006 (6)	0.0035 (6)	−0.0029 (6)
N3	0.0110 (6)	0.0156 (7)	0.0184 (7)	−0.0021 (5)	0.0035 (5)	−0.0013 (5)
C5	0.0114 (6)	0.0162 (8)	0.0167 (7)	0.0050 (6)	0.0006 (5)	0.0015 (6)
C6	0.0144 (7)	0.0226 (8)	0.0231 (8)	0.0053 (6)	0.0047 (6)	0.0050 (6)
C7	0.0261 (9)	0.0351 (11)	0.0225 (9)	0.0143 (8)	0.0097 (7)	0.0099 (7)
C8	0.0371 (10)	0.0367 (11)	0.0166 (8)	0.0175 (8)	0.0035 (7)	0.0002 (7)
C9	0.0254 (8)	0.0242 (9)	0.0215 (8)	0.0089 (7)	−0.0061 (6)	−0.0032 (7)
C10	0.0131 (7)	0.0175 (8)	0.0188 (7)	0.0048 (6)	−0.0047 (5)	0.0011 (6)
C11	0.0098 (6)	0.0157 (8)	0.0259 (8)	0.0017 (6)	−0.0048 (6)	0.0030 (6)
C12	0.0145 (7)	0.0189 (9)	0.0395 (10)	−0.0035 (7)	−0.0081 (7)	0.0056 (8)
C13	0.0122 (7)	0.0283 (10)	0.0525 (12)	−0.0042 (7)	−0.0001 (7)	0.0169 (9)
C14	0.0167 (8)	0.0314 (11)	0.0424 (11)	0.0031 (7)	0.0107 (7)	0.0164 (8)
C15	0.0173 (7)	0.0217 (9)	0.0295 (8)	0.0040 (6)	0.0090 (6)	0.0063 (7)
C16	0.0089 (6)	0.0152 (8)	0.0247 (8)	0.0025 (5)	0.0024 (5)	0.0048 (6)

Geometric parameters (Å, º) top

O1—C1	1.3723 (18)	C6—C7	1.387 (3)
O1—C2	1.3732 (18)	C6—H6	0.9500
C1—N1	1.332 (2)	C7—C8	1.399 (3)
C1—S1	1.6452 (16)	C7—H7	0.9500
N1—N2	1.3922 (18)	C8—C9	1.379 (3)
N1—H1N	0.89 (2)	C8—H8	0.9500
N2—C2	1.285 (2)	C9—C10	1.398 (2)
N2—O1ⁱ	2.9516 (18)	C9—H9	0.9500
C2—C3	1.480 (2)	C10—C11	1.445 (2)
C3—C4	1.540 (2)	C11—C12	1.396 (2)
C3—H6A	0.9900	C11—C16	1.411 (2)
C3—H3B	0.9900	C12—C13	1.383 (3)
C4—N3	1.442 (2)	C12—H12	0.9500
C4—H4A	0.9900	C13—C14	1.396 (3)
C4—H4B	0.9900	C13—H13	0.9500
N3—C16	1.386 (2)	C14—C15	1.396 (3)
N3—C5	1.387 (2)	C14—H14	0.9500
C5—C6	1.397 (2)	C15—C16	1.398 (2)
C5—C10	1.411 (2)	C15—H15	0.9500

C1—O1—C2	106.49 (12)	C7—C6—H6	121.4
N1—C1—O1	104.73 (13)	C5—C6—H6	121.4
N1—C1—S1	132.68 (13)	C6—C7—C8	121.53 (17)
O1—C1—S1	122.56 (12)	C6—C7—H7	119.2
C1—N1—N2	112.56 (13)	C8—C7—H7	119.2
C1—N1—H1N	125.4 (14)	C9—C8—C7	121.11 (17)
N2—N1—H1N	122.1 (14)	C9—C8—H8	119.4
C2—N2—N1	103.34 (13)	C7—C8—H8	119.4
C2—N2—O1ⁱ	165.93 (11)	C8—C9—C10	118.93 (18)
N1—N2—O1ⁱ	81.45 (9)	C8—C9—H9	120.5
N2—C2—O1	112.87 (13)	C10—C9—H9	120.5
N2—C2—C3	128.62 (15)	C9—C10—C5	119.30 (16)
O1—C2—C3	118.48 (14)	C9—C10—C11	134.28 (17)
C2—C3—C4	111.86 (13)	C5—C10—C11	106.41 (14)
C2—C3—H6A	109.2	C12—C11—C16	119.57 (17)
C4—C3—H6A	109.2	C12—C11—C10	133.50 (17)
C2—C3—H3B	109.2	C16—C11—C10	106.93 (14)
C4—C3—H3B	109.2	C13—C12—C11	118.63 (19)
H6A—C3—H3B	107.9	C13—C12—H12	120.7
N3—C4—C3	112.02 (13)	C11—C12—H12	120.7
N3—C4—H4A	109.2	C12—C13—C14	121.24 (17)
C3—C4—H4A	109.2	C12—C13—H13	119.4
N3—C4—H4B	109.2	C14—C13—H13	119.4
C3—C4—H4B	109.2	C15—C14—C13	121.73 (18)
H4A—C4—H4B	107.9	C15—C14—H14	119.1
C16—N3—C5	108.85 (13)	C13—C14—H14	119.1
C16—N3—C4	125.23 (14)	C14—C15—C16	116.51 (17)
C5—N3—C4	125.38 (13)	C14—C15—H15	121.7
N3—C5—C6	128.95 (15)	C16—C15—H15	121.7
N3—C5—C10	109.05 (14)	N3—C16—C15	128.93 (16)
C6—C5—C10	122.00 (15)	N3—C16—C11	108.74 (14)
C7—C6—C5	117.12 (17)	C15—C16—C11	122.32 (16)

C2—O1—C1—N1	−0.16 (15)	C8—C9—C10—C5	0.8 (2)
C2—O1—C1—S1	178.36 (11)	C8—C9—C10—C11	−179.84 (17)
O1—C1—N1—N2	0.37 (16)	N3—C5—C10—C9	179.65 (14)
S1—C1—N1—N2	−177.93 (12)	C6—C5—C10—C9	−1.3 (2)
C1—N1—N2—C2	−0.44 (17)	N3—C5—C10—C11	0.15 (17)
C1—N1—N2—O1ⁱ	166.09 (12)	C6—C5—C10—C11	179.21 (14)
N1—N2—C2—O1	0.32 (17)	C9—C10—C11—C12	1.0 (3)
O1ⁱ—N2—C2—O1	−108.2 (4)	C5—C10—C11—C12	−179.56 (18)
N1—N2—C2—C3	−177.54 (14)	C9—C10—C11—C16	−179.05 (17)
O1ⁱ—N2—C2—C3	73.9 (5)	C5—C10—C11—C16	0.35 (17)
C1—O1—C2—N2	−0.11 (17)	C16—C11—C12—C13	−0.3 (2)
C1—O1—C2—C3	177.99 (13)	C10—C11—C12—C13	179.55 (17)
N2—C2—C3—C4	102.47 (19)	C11—C12—C13—C14	0.1 (3)
O1—C2—C3—C4	−75.29 (17)	C12—C13—C14—C15	0.4 (3)
C2—C3—C4—N3	−62.96 (18)	C13—C14—C15—C16	−0.6 (3)
C3—C4—N3—C16	−79.78 (18)	C5—N3—C16—C15	179.80 (15)
C3—C4—N3—C5	90.85 (18)	C4—N3—C16—C15	−8.3 (3)
C16—N3—C5—C6	−179.58 (15)	C5—N3—C16—C11	0.82 (17)
C4—N3—C5—C6	8.5 (3)	C4—N3—C16—C11	172.75 (14)
C16—N3—C5—C10	−0.60 (17)	C14—C15—C16—N3	−178.53 (16)
C4—N3—C5—C10	−172.52 (14)	C14—C15—C16—C11	0.3 (2)
N3—C5—C6—C7	179.70 (15)	C12—C11—C16—N3	179.20 (14)
C10—C5—C6—C7	0.8 (2)	C10—C11—C16—N3	−0.72 (17)
C5—C6—C7—C8	0.0 (2)	C12—C11—C16—C15	0.1 (2)
C6—C7—C8—C9	−0.5 (3)	C10—C11—C16—C15	−179.78 (14)
C7—C8—C9—C10	0.0 (3)

Symmetry code: (i) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···S1ⁱ	0.89 (2)	2.75 (2)	3.6053 (14)	162.8 (19)
N1—H1N···O1ⁱ	0.89 (2)	2.62 (2)	3.0707 (18)	112.5 (16)
C3—H3B···S1ⁱⁱ	0.99	2.93	3.9061 (16)	169
C4—H4A···N2ⁱⁱⁱ	0.99	2.67	3.495 (2)	141
C4—H4B···Cg4ⁱⁱⁱ	0.99	2.87	3.4577 (17)	119
C12—H12···Cg4ⁱ	0.95	3.22	4.073 (2)	151

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

Acknowledgements

We thank the University of Otago for purchase of the diffractometer and the Chemistry Department University of Otago for support of the work of JS.

References

Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Billah, S. M. R., Christie, R. M. & Shamey, R. (2008). Coloration Technol. 124, 223–228. CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fitilis, I., Fakis, M., Polyzos, I., Giannetas, V., Persephonis, P., Vellis, P. & Mikroyannidis, J. (2007). Chem. Phys. Lett. 447, 300–304. Web of Science CrossRef CAS Google Scholar
Geier, M. J., Vogels, C. M., Decken, A. & Westcott, S. A. (2009). J. Organomet. Chem. 694, 3154–3159. Web of Science CSD CrossRef CAS Google Scholar
Ghoneim, O. M., Legere, J. A., Golbraikh, A., Tropsha, A. & Booth, R. G. (2006). Bioorg. Med. Chem. 14, 6640–6658. CrossRef PubMed CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hosomi, H., Ohba, S. & Ito, Y. (2000). Acta Cryst. C56, e147–e148. CSD CrossRef CAS IUCr Journals Google Scholar
Hunter, K. A. & Simpson, J. (1999). TITAN2000. University of Otago, New Zealand. Google Scholar
Kalinin, A. V., Scherer, S. & Snieckus, V. (2003). Angew. Chem. Int. Ed. 42, 3399–3404. CSD CrossRef CAS Google Scholar
Khan, I., Ibrar, A. & Simpson, J. (2014). CrystEngComm, 16, 164–174. CSD CrossRef CAS Google Scholar
Kimura, T., Kai, Y., Yasuoka, N. & Kasai, N. (1985). Bull. Chem. Soc. Jpn, 58, 2268–2271. CSD CrossRef CAS Web of Science Google Scholar
Lee, D. & Wallwork, S. C. (1978). Acta Cryst. B34, 3604–3608. CSD CrossRef CAS IUCr Journals Google Scholar
Li, C., Liu, M., Pschirer, N. G., Baumgarten, M. & Müllen, K. (2010). Chem. Rev. 110, 6817–6855. CrossRef CAS PubMed Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Matsuoka, M., Han, L., Kitao, T., Mochizuki, S. & Nakatsu, K. (1988). Chem. Lett. 17, 905–908. CSD CrossRef Google Scholar
Peng, Q., Liu, X., Qin, Y., Xu, J., Li, M. & Dai, L. (2011). J. Mater. Chem. 21, 7714–7722. CrossRef CAS Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
TePaske, M. R., Gloer, J. B., Wicklow, D. T. & Dowd, P. F. (1989). Tetrahedron Lett. 30, 5965–5968. CrossRef CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zheng, Z.-B., Wu, R.-T., Lu, J.-R. & Sun, Y.-F. (2006). Acta Cryst. E62, o4293–o4295. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, Q., Gao, Y. J., Gao, H. Y. & Jin, W. J. (2014). J. Photochem. Photobiol. Chem. 289, 31–38. Web of Science CSD CrossRef CAS Google Scholar

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Volume 73| Part 7| July 2017| Pages 1066-1069

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 5-[2-(9H-carbazol-9-yl)eth­yl]-1,3,4-oxa­diazole-2(3H)-thione

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure of 5-[2-(9H-carbazol-9-yl)ethyl]-1,3,4-oxadiazole-2(3H)-thione

3. Supramolecular features