1-(4-Methyl­phenyl­sulfon­yl)-1H-1,2,3-benzotriazole: sheets built from C—H⋯N, C—H⋯O and C—H⋯π(arene) hydrogen bonds

Rodríguez, R.; Nogueras, M.; Cobo, J.; Low, J.N.; Glidewell, C.

doi:10.1107/S1600536805024219

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 61| Part 9| September 2005| Pages o2795-o2797

https://doi.org/10.1107/S1600536805024219

1-(4-Methylphenylsulfonyl)-1H-1,2,3-benzotriazole: sheets built from C—H⋯N, C—H⋯O and C—H⋯π(arene) hydrogen bonds

Ricaurte Rodríguez,^a Manuel Nogueras,^a Justo Cobo,^a John N. Low ^b and Christopher Glidewell ^c ^*

^aDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 27 July 2005; accepted 28 July 2005; online 6 August 2005)

The molecules of the title compound, C₁₃H₁₁N₃O₂S, are linked into chains of edge-fused rings by a combination of C—H⋯N and C—H⋯O hydrogen bonds, and these chains are linked into sheets by a combination of a C—H⋯π(arene) hydrogen bond and a second, rather weak, C—H⋯O hydrogen bond.

Comment

Sulfonylbenzotriazole derivatives are versatile synthetic intermediates both as benzotriazolyl donors (Katritzky et al., 2001 ) and as sulfonyl donors (Katritzky et al., 2004 ) because both have good leaving groups. The sulfonylbenzotriazoles can be readily prepared from benzotriazole and sulfonyl chlorides or from 1-chlorobenzotriazole and sulfonic acids. We report here the structure of 1-(4-methylphenylsulfonyl)-1H-1,2,3-benzotriazole, (I), which was obtained adventitiously in 54% yield when the addition of benzotriazole to the double bond in (4S,5R,6R)-diphenylmethyl (E)-4,5,6,7-tetrahydroxy-2-heptenoate was attempted in the presence of 4-toluenesulfonic acid. The direct reaction between benzotriazole and 4-toluenesulfonic acid in ethanol under reflux did not give any product and addition of diphenylmethanol to such a mixture yielded only the reported 1-diphenylmethyl-benzotriazole (Märky et al., 1979 ), suggesting that transesterification, via a sulfonic ester, is required to produce the title compound in this way.

Within the molecules of (I), the bond distances (Table 1) show some evidence for modest bond fixation in the carbocyclic ring of the benzotriazole unit. Thus, the bonds C4—C5 and C6—C7 are significantly shorter than the bonds C3A—C4, C5—C6 and C7—C7A; the cross-ring bond C3A—C7A, expected to be the longest bond in this ring is, in fact, one of the shorter bonds. By contrast with this ring, the C—C distances in the benzenesulfonyl ring span the rather narrow range 1.386 (2)–1.395 (2) Å. There is clear bond fixation within the triazole ring. The exocyclic angles at the planar-configuration atom N1 differ by ca 10° and the O—S—O angle in the sulfonyl group is, as usually found in such fragments, much larger than the ideal tetrahedral value.

The molecules of (I) are linked by one C—H⋯N and one C—H⋯O hydrogen bond (Table 2) into chains of edge-fused rings. Aryl atom C16 in the molecule at (x, y, z) acts as hydrogen-bond donor to atom N2 in the molecule at (1 − x, 1 − y, 1 − z), so generating a centrosymmetric R₂²(8) motif (Bernstein et al., 1995 ); in addition, atom C12 at (x, y, z) acts as donor to atom O1 in the molecule at (−x, −y, −z), thus generating a second centrosymmetric R₂²(8) motif. The combination of these two motifs then generates a chain of edge-fused rings running parallel to the [111] direction with the rings built from C—H⋯N hydrogen bonds centred at (n + 0.5, n + 0.5, n + 0.5) (n = zero or integer) and the rings built from C—H⋯O hydrogen bonds centred at (n, n, n) (n = zero or integer) (Fig. 2).

Two further, but weaker, hydrogen bonds (Table 2) act co-operatively to link the [111] chains into sheets. Benzotriazole atoms C6 and C4 in the molecule at (x, y, z) act as hydrogen-bond donors, respectively, to atom O2 in the molecule at (x, −1 + y, z) and to aryl ring C11–C16 in the molecule at (1 − x, −y, 1 − z), both of which lie in a [111] chain offset from the reference chain by a unit translation along [010] (Fig. 3). Propagation by inversion of these hydrogen bonds then links [111] chains into (10 $[\overline{1}]$ ) sheets, but there are no direction-specific interactions between adjacent sheets.

Figure 1
The molecule of compound (I)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Stereoscopic view of part of the crystal structure of compound (I)

, showing the formation of a hydrogen-bonded chain along [111] containing two types of centrosymmetric R₂²(8) ring. For the sake of clarity, the H atoms not involved in the motifs shown have been omitted.

Figure 3
Stereoscopic view of part of the crystal structure of compound (I)

, showing the formation of a hydrogen-bonded chain along [010]. For the sake of clarity, the H atoms not involved in the motifs shown have been omitted.

Experimental

A solution of (4S,5R,6R)-diphenylmethyl (E)-4,5,6,7-tetrahydroxy-2-heptenoate (0.15 g, 0.418 mmol), benzotriazole (0.05 g, 0.4 mmol) and 4-toluenesulfonic acid monohydrate (0.078 g, 0.41 mmol) in ethanol (20 ml) was heated under reflux for 45 min. The reaction mixture was cooled and then neutralized with saturated aqueous sodium carbonate solution; this neutralized mixture was then extracted with diethyl ether (2 × 10 ml). The organic extract was dried with sodium sulfate and the solvent was removed under reduced pressure to give the title compound in 54% yield (m.p. 407–409 K). Crystals suitable for single-crystal X-ray diffraction were grown from a solution in diethyl ether.

Crystal data

C₁₃H₁₁N₃O₂S
M_r = 273.31
Triclinic, $[P \overline 1]$
a = 7.4211 (3) Å
b = 9.2176 (3) Å
c = 9.7823 (3) Å
α = 98.614 (3)°
β = 104.249 (2)°
γ = 102.684 (3)°
V = 617.87 (4) Å³
Z = 2
D_x = 1.469 Mg m⁻³
Mo Kα radiation
Cell parameters from 2825 reflections
θ = 4.1–27.5°
μ = 0.26 mm⁻¹
T = 120 (2) K
Needle, colourless
0.42 × 0.18 × 0.13 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan(SADABS; Sheldrick, 2003 )T_min = 0.931, T_max = 0.967
14360 measured reflections
2825 independent reflections
2398 reflections with I > 2σ(I)
R_int = 0.036
θ_max = 27.5°
h = −9 → 9
k = −11 → 11
l = −12 → 12

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.05
2825 reflections
173 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0482P)² + 0.2971P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1—N2	1.390 (2)
N2—N3	1.288 (2)
N3—C3A	1.387 (2)
C3A—C7A	1.394 (2)
C7A—N1	1.3821 (19)
C3A—C4	1.402 (2)
C4—C5	1.375 (2)
C5—C6	1.407 (2)
C6—C7	1.382 (2)
C7—C7A	1.396 (2)

N2—N1—S1	119.98 (10)
C7A—N1—S1	129.49 (11)
N2—N1—C7A	109.89 (12)
O1—S1—O2	121.89 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg1ⁱ	0.95	2.84	3.641 (2)	143
C6—H6⋯O2ⁱⁱ	0.95	2.59	3.247 (2)	127
C12—H12⋯O1ⁱⁱⁱ	0.95	2.48	3.244 (2)	137
C16—H16⋯N2^iv	0.95	2.62	3.299 (2)	129
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x, y-1, z; (iii) -x, -y, -z; (iv) -x+1, -y+1, -z+1.

All H atoms were located from difference maps and then treated as riding atoms, with C—H = 0.95 (aromatic) or 0.98 Å (methyl) and U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C).

Data collection: COLLECT (Hooft, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL 97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536805024219/lh6480sup1.cif

Structure factors: contains datablock 691. DOI: https://doi.org/10.1107/S1600536805024219/lh6480Isup2.hkl

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL 97 and PRPKAPPA (Ferguson, 1999).

1-(4-Methylphenylsulfonyl)-1H-1,2,3-benzotriazole top

Crystal data top

C₁₃H₁₁N₃O₂S	Z = 2
M_r = 273.31	F(000) = 284
Triclinic, P1	D_x = 1.469 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4211 (3) Å	Cell parameters from 2825 reflections
b = 9.2176 (3) Å	θ = 4.1–27.5°
c = 9.7823 (3) Å	µ = 0.26 mm⁻¹
α = 98.614 (3)°	T = 120 K
β = 104.249 (2)°	Needle, colourless
γ = 102.684 (3)°	0.42 × 0.18 × 0.13 mm
V = 617.87 (4) Å³

Data collection top

Bruker–Nonius 95mm CCD camera on κ goniostat diffractometer	2825 independent reflections
Radiation source: Bruker–Nonius FR91 rotating anode	2398 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 4.1°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −11→11
T_min = 0.931, T_max = 0.967	l = −12→12
14360 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0482P)² + 0.2971P] where P = (F_o² + 2F_c²)/3
2825 reflections	(Δ/σ)_max < 0.001
173 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

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

	x	y	z	U_iso*/U_eq
S1	0.11158 (5)	0.24195 (4)	0.27755 (4)	0.01978 (12)
O1	−0.04859 (16)	0.12509 (12)	0.18262 (12)	0.0239 (3)
O2	0.09049 (17)	0.38368 (12)	0.34172 (13)	0.0271 (3)
N1	0.19364 (18)	0.16134 (14)	0.41598 (13)	0.0192 (3)
N2	0.30931 (19)	0.25264 (15)	0.54843 (14)	0.0233 (3)
N3	0.36838 (19)	0.16548 (15)	0.63068 (14)	0.0237 (3)
C3A	0.2980 (2)	0.01522 (18)	0.55519 (16)	0.0203 (3)
C4	0.3228 (2)	−0.11862 (19)	0.59964 (17)	0.0243 (3)
C5	0.2353 (2)	−0.25318 (19)	0.49941 (18)	0.0255 (3)
C6	0.1253 (2)	−0.25627 (18)	0.35900 (18)	0.0245 (3)
C7	0.0970 (2)	−0.12581 (17)	0.31394 (17)	0.0219 (3)
C7A	0.1871 (2)	0.01037 (16)	0.41622 (16)	0.0181 (3)
C11	0.2978 (2)	0.27397 (17)	0.19644 (16)	0.0195 (3)
C12	0.2910 (2)	0.16746 (19)	0.07693 (17)	0.0247 (3)
C13	0.4358 (3)	0.1974 (2)	0.01053 (17)	0.0283 (4)
C14	0.5868 (2)	0.3303 (2)	0.06199 (17)	0.0262 (4)
C15	0.5907 (2)	0.43337 (19)	0.18311 (18)	0.0270 (4)
C16	0.4467 (2)	0.40703 (17)	0.25090 (17)	0.0233 (3)
C141	0.7412 (3)	0.3617 (2)	−0.0133 (2)	0.0364 (4)
H4	0.3968	−0.1164	0.6946	0.029*
H5	0.2493	−0.3462	0.5256	0.031*
H6	0.0685	−0.3516	0.2927	0.029*
H7	0.0211	−0.1286	0.2195	0.026*
H12	0.1892	0.0762	0.0417	0.030*
H13	0.4321	0.1260	−0.0716	0.034*
H14A	0.8119	0.4697	0.0173	0.055*
H14B	0.6814	0.3363	−0.1180	0.055*
H14C	0.8307	0.2995	0.0120	0.055*
H15	0.6941	0.5235	0.2200	0.032*
H16	0.4499	0.4785	0.3328	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0225 (2)	0.0162 (2)	0.0206 (2)	0.00567 (15)	0.00558 (15)	0.00415 (14)
O1	0.0221 (5)	0.0214 (6)	0.0243 (6)	0.0029 (4)	0.0020 (5)	0.0053 (4)
O2	0.0341 (6)	0.0182 (6)	0.0333 (6)	0.0105 (5)	0.0144 (5)	0.0055 (5)
N1	0.0224 (6)	0.0159 (6)	0.0167 (6)	0.0034 (5)	0.0042 (5)	0.0007 (5)
N2	0.0249 (7)	0.0224 (7)	0.0180 (6)	0.0025 (5)	0.0052 (5)	−0.0019 (5)
N3	0.0235 (7)	0.0278 (7)	0.0176 (6)	0.0046 (6)	0.0056 (5)	0.0020 (5)
C3A	0.0181 (7)	0.0266 (8)	0.0168 (7)	0.0057 (6)	0.0072 (6)	0.0035 (6)
C4	0.0226 (8)	0.0338 (9)	0.0217 (8)	0.0115 (7)	0.0087 (6)	0.0121 (7)
C5	0.0270 (8)	0.0256 (8)	0.0313 (9)	0.0117 (7)	0.0130 (7)	0.0135 (7)
C6	0.0258 (8)	0.0187 (7)	0.0291 (9)	0.0057 (6)	0.0091 (7)	0.0043 (6)
C7	0.0242 (8)	0.0200 (8)	0.0192 (7)	0.0052 (6)	0.0039 (6)	0.0024 (6)
C7A	0.0189 (7)	0.0177 (7)	0.0191 (7)	0.0049 (6)	0.0074 (6)	0.0047 (6)
C11	0.0224 (7)	0.0196 (7)	0.0171 (7)	0.0062 (6)	0.0049 (6)	0.0059 (6)
C12	0.0279 (8)	0.0238 (8)	0.0184 (7)	0.0052 (6)	0.0026 (6)	0.0021 (6)
C13	0.0335 (9)	0.0335 (9)	0.0180 (8)	0.0117 (7)	0.0068 (7)	0.0031 (7)
C14	0.0265 (8)	0.0342 (9)	0.0217 (8)	0.0111 (7)	0.0072 (7)	0.0127 (7)
C15	0.0257 (8)	0.0261 (8)	0.0278 (9)	0.0036 (7)	0.0063 (7)	0.0087 (7)
C16	0.0276 (8)	0.0189 (7)	0.0219 (8)	0.0051 (6)	0.0056 (6)	0.0041 (6)
C141	0.0321 (9)	0.0555 (12)	0.0311 (9)	0.0170 (9)	0.0152 (8)	0.0198 (9)

Geometric parameters (Å, º) top

N1—N2	1.390 (2)	C12—C13	1.386 (2)
N2—N3	1.288 (2)	C12—H12	0.95
N3—C3A	1.387 (2)	C13—C14	1.395 (2)
C3A—C7A	1.394 (2)	C13—H13	0.95
C7A—N1	1.3821 (19)	C14—C15	1.393 (2)
C3A—C4	1.402 (2)	C14—C141	1.507 (2)
C4—C5	1.375 (2)	C141—H14A	0.98
C5—C6	1.407 (2)	C141—H14B	0.98
C6—C7	1.382 (2)	C141—H14C	0.98
C7—C7A	1.396 (2)	C15—C16	1.387 (2)
N1—S1	1.6885 (13)	C15—H15	0.95
S1—O2	1.4205 (11)	C16—H16	0.95
S1—O1	1.4248 (11)	C4—H4	0.95
S1—C11	1.7486 (15)	C5—H5	0.95
C11—C16	1.389 (2)	C6—H6	0.95
C11—C12	1.392 (2)	C7—H7	0.95

N2—N1—S1	119.98 (10)	C16—C15—C14	121.32 (15)
C7A—N1—S1	129.49 (11)	C16—C15—H15	119.3
N2—N1—C7A	109.89 (12)	C14—C15—H15	119.3
O1—S1—O2	121.89 (7)	C15—C16—C11	118.58 (15)
O2—S1—N1	105.81 (7)	C15—C16—H16	120.7
O1—S1—N1	103.96 (6)	C11—C16—H16	120.7
O2—S1—C11	109.56 (7)	N3—N2—N1	108.15 (12)
O1—S1—C11	109.29 (7)	N2—N3—C3A	109.35 (13)
N1—S1—C11	104.84 (7)	N3—C3A—C7A	108.99 (13)
C16—C11—C12	121.61 (15)	N3—C3A—C4	129.97 (14)
C16—C11—S1	119.06 (12)	C7A—C3A—C4	121.03 (14)
C12—C11—S1	119.31 (12)	C5—C4—C3A	116.89 (14)
C13—C12—C11	118.56 (15)	C5—C4—H4	121.6
C13—C12—H12	120.7	C3A—C4—H4	121.6
C11—C12—H12	120.7	C4—C5—C6	121.48 (15)
C12—C13—C14	121.27 (15)	C4—C5—H5	119.3
C12—C13—H13	119.4	C6—C5—H5	119.3
C14—C13—H13	119.4	C7—C6—C5	122.44 (15)
C15—C14—C13	118.65 (15)	C7—C6—H6	118.8
C15—C14—C141	120.97 (16)	C5—C6—H6	118.8
C13—C14—C141	120.37 (16)	C6—C7—C7A	115.69 (14)
C14—C141—H14A	109.5	C6—C7—H7	122.2
C14—C141—H14B	109.5	C7A—C7—H7	122.2
H14A—C141—H14B	109.5	N1—C7A—C3A	103.57 (13)
C14—C141—H14C	109.5	N1—C7A—C7	133.95 (14)
H14A—C141—H14C	109.5	C3A—C7A—C7	122.46 (14)
H14B—C141—H14C	109.5

C7A—N1—S1—O2	159.42 (13)	S1—C11—C16—C15	−178.13 (12)
N2—N1—S1—O2	−30.75 (13)	C7A—N1—N2—N3	−2.03 (16)
C7A—N1—S1—O1	29.92 (15)	S1—N1—N2—N3	−173.70 (10)
N2—N1—S1—O1	−160.25 (11)	N1—N2—N3—C3A	1.29 (16)
C7A—N1—S1—C11	−84.79 (14)	N2—N3—C3A—C7A	−0.12 (17)
N2—N1—S1—C11	85.03 (12)	N2—N3—C3A—C4	−179.63 (15)
O2—S1—C11—C16	27.59 (14)	N3—C3A—C4—C5	−179.67 (15)
O1—S1—C11—C16	163.52 (12)	C7A—C3A—C4—C5	0.9 (2)
N1—S1—C11—C16	−85.56 (13)	C3A—C4—C5—C6	−0.2 (2)
O2—S1—C11—C12	−150.89 (12)	C4—C5—C6—C7	−0.7 (2)
O1—S1—C11—C12	−14.97 (14)	C5—C6—C7—C7A	0.9 (2)
N1—S1—C11—C12	95.96 (13)	N2—N1—C7A—C3A	1.86 (16)
C16—C11—C12—C13	−0.9 (2)	S1—N1—C7A—C3A	172.49 (11)
S1—C11—C12—C13	177.53 (12)	N2—N1—C7A—C7	−179.17 (16)
C11—C12—C13—C14	0.5 (2)	S1—N1—C7A—C7	−8.5 (3)
C12—C13—C14—C15	0.4 (3)	N3—C3A—C7A—N1	−1.08 (16)
C12—C13—C14—C141	−179.08 (15)	C4—C3A—C7A—N1	178.48 (13)
C13—C14—C15—C16	−1.0 (2)	N3—C3A—C7A—C7	179.80 (13)
C141—C14—C15—C16	178.45 (15)	C4—C3A—C7A—C7	−0.6 (2)
C14—C15—C16—C11	0.7 (2)	C6—C7—C7A—N1	−179.09 (16)
C12—C11—C16—C15	0.3 (2)	C6—C7—C7A—C3A	−0.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg1ⁱ	0.95	2.84	3.641 (2)	143
C6—H6···O2ⁱⁱ	0.95	2.59	3.247 (2)	127
C12—H12···O1ⁱⁱⁱ	0.95	2.48	3.244 (2)	137
C16—H16···N2^iv	0.95	2.62	3.299 (2)	129

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

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England JC and MN thank the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. RR thanks FUNDACIÓN CAROLINA for a fellowship grant.

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