Bis(1-tosyl-2-pyrrol-yl)ethyne.

The title mol-ecule, C(24)H(20)N(2)O(4)S(2), has crystallographic inversion symmetry with a triple-bond distance of 1.206 (2) Å. The alkyne is not quite linear, with a C-C C angle of 175.78 (16)°. The planar pyrrole rings are parallel but offset from coplanarity by 0.318 (1) Å. The conformation of the sulfonyl group with respect to the pyrrole ring is such that an O atom is nearly eclipsed with this ring, having an O-S-N-C torsion angle of 3.48 (11)°. C-H⋯O inter-actions [C⋯O 3.278 (2) Å, 136° about H] between pyrrole H and sulfonyl O atoms lead to the formation of ladder-like chains.

Related literature

For related structures, see Abell et al. (1998 ▶); Knight et al. (2003 ▶); Tanui et al. (2008 ▶). For related literature, see: Vogel (1996 ▶); Chinchilla & Najera (2007 ▶); Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C24H20N2O4S2

M = 464.54

Monoclinic,

a = 8.5127 (15) Å

b = 16.822 (2) Å

c = 7.5311 (11) Å

β = 101.049 (7)°

V = 1058.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.29 mm−1

T = 90 K

0.35 × 0.30 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer (with Oxford Cryostream)

Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.896, T max = 0.966

16546 measured reflections

3565 independent reflections

2995 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.05

3565 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.54 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: HKL DENZO (Otwinowski & Minor, 1997 ▶) and HKL SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062964/tk2223sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062964/tk2223Isup2.hkl

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

C24H20N2O4S2	F000 = 484
Mr = 464.54	Dx = 1.458 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3246 reflections
a = 8.5127 (15) Å	θ = 2.5–32.5º
b = 16.822 (2) Å	µ = 0.29 mm−1
c = 7.5311 (11) Å	T = 90 K
β = 101.049 (7)º	Fragment, colorless
V = 1058.5 (3) Å3	0.35 × 0.30 × 0.12 mm
Z = 2

Nonius KappaCCD (with Oxford Cryostream) diffractometer	3565 independent reflections
Radiation source: fine-focus sealed tube	2995 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
T = 90 K	θmax = 32.6º
ω scans with κ offsets	θmin = 2.7º
Absorption correction: multi-scan(HKL SCALEPACK; Otwinowski & Minor 1997)	h = −12→12
Tmin = 0.896, Tmax = 0.966	k = −20→24
16546 measured reflections	l = −11→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0457P)2 + 0.5421P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.39 e Å−3
3565 reflections	Δρmin = −0.54 e Å−3
147 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0087 (19)
Secondary atom site location: difference Fourier map

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
S1	0.17966 (3)	0.588570 (17)	0.18361 (4)	0.01389 (9)
O1	0.03490 (11)	0.62987 (6)	0.10845 (12)	0.0205 (2)
O2	0.21216 (11)	0.51113 (5)	0.12117 (12)	0.01826 (19)
N1	0.17450 (12)	0.58026 (6)	0.40533 (13)	0.01363 (19)
C1	0.04720 (14)	0.60559 (7)	0.48222 (16)	0.0155 (2)
H1	−0.0438	0.6342	0.4222	0.019*
C2	0.07578 (14)	0.58208 (7)	0.65906 (16)	0.0159 (2)
H2	0.0083	0.5915	0.7437	0.019*
C3	0.22451 (15)	0.54103 (7)	0.69389 (15)	0.0154 (2)
H3	0.2736	0.5181	0.8061	0.018*
C4	0.28522 (14)	0.54024 (7)	0.53683 (15)	0.0135 (2)
C5	0.43438 (14)	0.51145 (7)	0.50710 (15)	0.0143 (2)
C6	0.34514 (14)	0.64976 (7)	0.17831 (15)	0.0141 (2)
C7	0.33400 (15)	0.73131 (7)	0.20914 (16)	0.0169 (2)
H7	0.2372	0.7541	0.2306	0.020*
C8	0.46788 (16)	0.77829 (7)	0.20758 (17)	0.0187 (2)
H8	0.4622	0.8338	0.2286	0.022*
C9	0.61100 (15)	0.74548 (8)	0.17564 (16)	0.0183 (2)
C10	0.61811 (15)	0.66412 (8)	0.14272 (16)	0.0172 (2)
H10	0.7143	0.6414	0.1193	0.021*
C11	0.48522 (14)	0.61580 (7)	0.14388 (15)	0.0151 (2)
H11	0.4903	0.5604	0.1214	0.018*
C12	0.75453 (18)	0.79796 (9)	0.1772 (2)	0.0262 (3)
H12A	0.8386	0.7676	0.1351	0.039*
H12B	0.7946	0.8170	0.3005	0.039*
H12C	0.7238	0.8435	0.0968	0.039*

	U11	U22	U33	U12	U13	U23
S1	0.01179 (14)	0.01874 (15)	0.01119 (13)	−0.00136 (10)	0.00237 (9)	0.00013 (9)
O1	0.0125 (4)	0.0318 (5)	0.0161 (4)	0.0012 (4)	0.0001 (3)	0.0038 (4)
O2	0.0202 (4)	0.0203 (4)	0.0152 (4)	−0.0047 (3)	0.0056 (3)	−0.0036 (3)
N1	0.0112 (4)	0.0182 (5)	0.0119 (4)	0.0008 (3)	0.0032 (3)	0.0007 (3)
C1	0.0121 (5)	0.0191 (5)	0.0164 (5)	0.0016 (4)	0.0051 (4)	0.0000 (4)
C2	0.0140 (5)	0.0188 (5)	0.0160 (5)	0.0004 (4)	0.0060 (4)	−0.0012 (4)
C3	0.0150 (5)	0.0186 (5)	0.0136 (5)	0.0005 (4)	0.0051 (4)	0.0003 (4)
C4	0.0123 (5)	0.0160 (5)	0.0122 (5)	0.0006 (4)	0.0028 (4)	0.0000 (4)
C5	0.0141 (5)	0.0173 (5)	0.0118 (4)	0.0001 (4)	0.0032 (4)	0.0012 (4)
C6	0.0133 (5)	0.0174 (5)	0.0117 (5)	−0.0011 (4)	0.0028 (4)	0.0017 (4)
C7	0.0178 (5)	0.0179 (5)	0.0151 (5)	0.0020 (4)	0.0029 (4)	0.0012 (4)
C8	0.0239 (6)	0.0159 (5)	0.0159 (5)	−0.0012 (4)	0.0030 (4)	0.0015 (4)
C9	0.0185 (6)	0.0211 (6)	0.0146 (5)	−0.0052 (4)	0.0017 (4)	0.0034 (4)
C10	0.0138 (5)	0.0214 (6)	0.0166 (5)	−0.0004 (4)	0.0038 (4)	0.0037 (4)
C11	0.0154 (5)	0.0161 (5)	0.0141 (5)	0.0003 (4)	0.0039 (4)	0.0017 (4)
C12	0.0254 (7)	0.0283 (7)	0.0256 (6)	−0.0114 (5)	0.0062 (5)	0.0019 (5)

S1—O2	1.4298 (10)	C6—C11	1.3907 (17)
S1—O1	1.4333 (10)	C6—C7	1.3977 (17)
S1—N1	1.6845 (10)	C7—C8	1.3888 (18)
S1—C6	1.7513 (12)	C7—H7	0.9500
N1—C1	1.3900 (15)	C8—C9	1.3997 (19)
N1—C4	1.4016 (15)	C8—H8	0.9500
C1—C2	1.3656 (17)	C9—C10	1.3945 (18)
C1—H1	0.9500	C9—C12	1.5056 (18)
C2—C3	1.4218 (17)	C10—C11	1.3944 (17)
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.3786 (16)	C11—H11	0.9500
C3—H3	0.9500	C12—H12A	0.9800
C4—C5	1.4164 (16)	C12—H12B	0.9800
C5—C5i	1.206 (2)	C12—H12C	0.9800
O2—S1—O1	121.17 (6)	C11—C6—S1	119.01 (9)
O2—S1—N1	107.09 (5)	C7—C6—S1	119.51 (9)
O1—S1—N1	104.35 (5)	C8—C7—C6	118.37 (11)
O2—S1—C6	108.71 (6)	C8—C7—H7	120.8
O1—S1—C6	109.91 (6)	C6—C7—H7	120.8
N1—S1—C6	104.20 (5)	C7—C8—C9	121.32 (12)
C1—N1—C4	108.98 (9)	C7—C8—H8	119.3
C1—N1—S1	123.92 (8)	C9—C8—H8	119.3
C4—N1—S1	126.76 (8)	C10—C9—C8	119.11 (11)
C2—C1—N1	108.07 (10)	C10—C9—C12	120.93 (12)
C2—C1—H1	126.0	C8—C9—C12	119.96 (12)
N1—C1—H1	126.0	C11—C10—C9	120.54 (12)
C1—C2—C3	107.85 (10)	C11—C10—H10	119.7
C1—C2—H2	126.1	C9—C10—H10	119.7
C3—C2—H2	126.1	C6—C11—C10	119.17 (11)
C4—C3—C2	108.26 (10)	C6—C11—H11	120.4
C4—C3—H3	125.9	C10—C11—H11	120.4
C2—C3—H3	125.9	C9—C12—H12A	109.5
C3—C4—N1	106.85 (10)	C9—C12—H12B	109.5
C3—C4—C5	129.33 (11)	H12A—C12—H12B	109.5
N1—C4—C5	123.67 (10)	C9—C12—H12C	109.5
C5i—C5—C4	175.78 (16)	H12A—C12—H12C	109.5
C11—C6—C7	121.47 (11)	H12B—C12—H12C	109.5
O2—S1—N1—C1	−126.14 (10)	O2—S1—C6—C11	−9.04 (11)
O1—S1—N1—C1	3.48 (11)	O1—S1—C6—C11	−143.78 (9)
C6—S1—N1—C1	118.78 (10)	N1—S1—C6—C11	104.90 (10)
O2—S1—N1—C4	46.48 (11)	O2—S1—C6—C7	171.15 (9)
O1—S1—N1—C4	176.09 (10)	O1—S1—C6—C7	36.41 (11)
C6—S1—N1—C4	−68.61 (11)	N1—S1—C6—C7	−74.92 (10)
C4—N1—C1—C2	−0.14 (13)	C11—C6—C7—C8	−1.01 (17)
S1—N1—C1—C2	173.61 (9)	S1—C6—C7—C8	178.80 (9)
N1—C1—C2—C3	−0.01 (14)	C6—C7—C8—C9	0.15 (18)
C1—C2—C3—C4	0.16 (14)	C7—C8—C9—C10	0.76 (18)
C2—C3—C4—N1	−0.24 (13)	C7—C8—C9—C12	−179.25 (12)
C2—C3—C4—C5	175.18 (12)	C8—C9—C10—C11	−0.83 (18)
C1—N1—C4—C3	0.23 (13)	C12—C9—C10—C11	179.17 (11)
S1—N1—C4—C3	−173.29 (9)	C7—C6—C11—C10	0.93 (17)
C1—N1—C4—C5	−175.51 (11)	S1—C6—C11—C10	−178.88 (9)
S1—N1—C4—C5	10.97 (17)	C9—C10—C11—C6	0.01 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ii	0.95	2.53	3.278 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.53	3.278 (2)	136

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