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N-[3-(Prop-1-yn-1-yl)phenyl]benzenesulfonamide

Leslie W. Pineda and Jorge A. Cabezas

IUCrData (2019). 4, x191176

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IUCrData (2019). 4, x191176 https://doi.org/10.1107/S2414314619011763 1 of 3

N-[3-(Prop-1-yn-1-yl)phenyl]benzenesulfonamide

Leslie W. Pinedaa,b and Jorge A. Cabezasa*

aEscuela de Quı́mica, Universidad de Costa Rica, 11501-2060, San José, Costa Rica, and bCentro de Electroquı́mica y

Energı́a Quı́mica (CELEQ), Universidad de Costa Rica, 11501-2060, San José, Costa Rica. *Correspondence e-mail:

jorge.cabezas@ucr.ac.cr

In the title sulfanilamide derivative, C15H13NO2S, which shows significant

activity against Staphylococcus aureus and Escherichia coli, the dihedral angle

between the planes of the aromatic rings is 62.15 (19)� and the four-coordinate S

atom adopts an almost ideal tetrahedral geometry. In the crystal, N—H� � �O and

C—H� � �O hydrogen bonds link the molecules into a three-dimensional

network.

Structure description

In 1932, a drug called Prontosil was discovered by the pharmaceutical division of IG

Farbenindustrie, an industrial conglomerate of German companies, including Bayer

Company. It was found to be very successful treating several diseases in humans,

provoked by Staphylococcus and Streptococcus. Prontosil was the first antibacterial drug,

with life-saving capability, to be used systematically for the treatment of bacterial

infections in the body. It belongs to a family of compounds called sulfa drugs or sulfo-

namides. In the 1940s and 1950s, most of the sulfa drugs were replaced by penicillin and

other drugs, which proved to be more effective against more types of bacteria. However,

nowadays, some sulfa drugs such as sulfamethoxazole, in combination with trimethoprim

(co-trimoxazole), are still used extensively to inhibit the growth of bacteria that produce

opportunistic infections in patients with AIDS, and bacterial infections such as pneu-

monia, bronchitis and infections of the urinary tract, ears and intestines (Brumfitt &

Hamilton-Miller, 1993).

As part of our studies in this area we now report the synthesis of of the title sulfani-

lamide derivative, 1, and its crystal structure. This compound, has been found to be very

effective against Staphylococcus aureus and Escherichia coli, and minimal inhibitory

concentrations (MIC) of 12.5 mg ml�1 and 25.0 mg ml�1 have been obtained respectively

(Cabezas & Arias, 2019).

Received 30 July 2019

Accepted 26 August 2019

Edited by W. T. A. Harrison, University of

Aberdeen, Scotland

Keywords: crystal structure; antibacterial

activity; N—H� � �O hydrogen bonding; propyne

substituent; sulfonamide.

CCDC reference: 1887179

Structural data: full structural data are available

from iucrdata.iucr.org

ISSN 2414-3146

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2 of 3 Pineda and Cabezas � C15H13NO2S IUCrData (2019). 4, x191176

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The crystal structure of 1 has monoclinic symmetry with one

molecule in the asymmetric unit: the molecular structure

consists of a benzenesulfonamide fragment bound to a

benzene ring bearing in its 3-position a propyne substituent

(Fig. 1): the dihedral angle between the C1–C6 and C10–C15

benzene rings is 62.15 (19)�. The length of the carbon–carbon

triple bond (C7 C8) is 1.181 (5) Å, with the C7—C8—C9 and

C8—C7—C1 angles being 178.8 (4) and 178.1 (4)�, respec-

tively, which are slightly distorted from the expected linear

geometry. The calculation of the angular structural index (�4 =

0.94; and �4’ = 0.90) for the four-coordinate S1 atom, which

binds to O1, O2, N1 and C10 from the benzene ring (Yang et

al., 2007; Okuniewski et al., 2015; Rosiak et al., 2018) indicates

that it adopts an almost ideal tetrahedral geometry (�4 = 0 for

an ideal square and 1 for an ideal tetrahedron). In the

extended structure of 1, weak N1—H1� � �O2, C4—H4� � �O1

and C6—H6� � �O1 hydrogen bonds are observed (Table 1,

Fig. 2), leading to the formation of a three-dimensional

network.

Table 1
Hydrogen-bond geometry (Å, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A
N1—H1� � �O2i 0.88 2.55 2.984 (4) 111
C4—H4� � �O1ii 0.95 2.45 3.256 (4) 143
C6—H6� � �O1 0.95 2.39 2.955 (4) 118

Symmetry codes: (i) x;�y þ 1; zþ 1
2; (ii) x; y; z þ 1.

Figure 2
Part of an [001] hydrogen-bonded chain with N—H� � �O2, C—H� � �O1
hydrogen bonds shown as green lines.

Figure 3
A synthetic scheme for the preparation of the title compound.

Figure 1
The title molecule with 50% probability ellipsoids.

Table 2
Experimental details.

Crystal data
Chemical formula C15H13NO2S
Mr 271.32
Crystal system, space group Monoclinic, Cc
Temperature (K) 100
a, b, c (Å) 8.4596 (4), 24.9769 (13), 7.1310 (4)
� (�) 117.557 (2)
V (Å3) 1335.80 (12)
Z 4
Radiation type Mo K�
� (mm�1) 0.24
Crystal size (mm) 0.35 � 0.20 � 0.15

Data collection
Diffractometer Bruker D8 Venture CCD
Absorption correction Multi-scan (SADABS; Bruker,

2015)
Tmin, Tmax 0.704, 0.746
No. of measured, independent and

observed [I > 2�(I)] reflections
9630, 3028, 2716

Rint 0.037
(sin �/�)max (�1) 0.649

Refinement
R[F 2 > 2�(F 2)], wR(F 2), S 0.042, 0.089, 1.03
No. of reflections 3028
No. of parameters 173
No. of restraints 2
H-atom treatment H-atom parameters constrained
�	max, �	min (e �3) 0.39, �0.47
Absolute structure Flack x determined using 1163

quotients [(I+)�(I�)]/[(I+)+(I�)]
(Parsons et al., 2013)

Absolute structure parameter 0.02 (3)

Computer programs: APEX3 and SAINT (Bruker, 2015), SHELXT (Sheldrick, 2015a),
SHELXL2014 (Sheldrick, 2015b), Mercury (Macrae et al., 2006) and publCIF (Westrip,
2010).

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IUCrData (2019). 4, x191176 Pineda and Cabezas � C15H13NO2S 3 of 3

Synthesis and crystallization

The title compound, 1, was synthesized by treatment of 3-

iodoaniline, 2, with benzenesulfonyl chloride, 3, in the

presence of pyridine, at room temperature to obtain, after

purification by column chromatography (ether:hexane, 40:60),

iodosulfonamide, 4, in 75% yield. This aromatic iodide 4, was

treated with propyne, under Sonogashira’s reaction conditions

(Sonogashira et al., 1975), using CuI and (Ph3P)2PdCl2 as

catalysts, (Fig. 3). After purification by column chromato-

graphy, using a solvent mixture of hexane:ethyl acetate

(75:25), compound 1 was isolated in 70% yield, and with an

overall yield of 53%. The product was recrystallized from

ethyl acetate solution at room temperature to result in light-

yellow blocks of the title compound.

Refinement

Crystal data, data collection and structure refinement are

summarized in Table 2.

Acknowledgements

CELEQ is thanked for supplying liquid nitrogen for the X-ray

measurements.

Funding information

Funding for this research was provided by: Vicerrectorı́a de

Investigación, Universidad de Costa Rica (UCR); Escuela de

Quı́mica (UCR).

References

Bruker (2015). APEX3, SAINT and SADABS. Bruker AXS Inc.,
Madison, Wisconsin, USA.

Brumfitt, W. & Hamilton-Miller, J. M. (1993). J. Chemother. 5, 465–
469.

Cabezas, J. A. & Arias, M. L. (2019). Int. J. Curr. Res, 11, 5224–5227.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P.,

Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39,
453–457.

Okuniewski, A., Rosiak, D., Chojnacki, J. & Becker, B. (2015).
Polyhedron, 90, 47–57.

Rosiak, D., Okuniewski, A. & Chojnacki, J. (2018). Polyhedron, 146,
35–41.

Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.
Sonogashira, K., Tohda, Y. & Hagihara, N. (1975). Tetrahedron Lett.
16, 4467–4470.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
Yang, L., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 955–

964.

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data-1IUCrData (2019). 4, x191176    

full crystallographic data

IUCrData (2019). 4, x191176    [https://doi.org/10.1107/S2414314619011763]

N-[3-(Prop-1-yn-1-yl)phenyl]benzenesulfonamide

Leslie W. Pineda and Jorge A. Cabezas

N-[3-(Prop-1-yn-1-yl)phenyl]benzenesulfonamide

Crystal data 

C15H13NO2S
Mr = 271.32
Monoclinic, Cc
a = 8.4596 (4) Å
b = 24.9769 (13) Å
c = 7.1310 (4) Å
β = 117.557 (2)°
V = 1335.80 (12) Å3

Z = 4

F(000) = 568
Dx = 1.349 Mg m−3

Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 4995 reflections
θ = 2.8–27.5°
µ = 0.24 mm−1

T = 100 K
Block, clear light yellow
0.35 × 0.20 × 0.15 mm

Data collection 

Bruker D8 Venture CCD 
diffractometer

Radiation source: Incoatec Microsource
Mirrors monochromator
Detector resolution: 10.4167 pixels mm-1

ω scans
Absorption correction: multi-scan 

(SADABS; Bruker, 2015)
Tmin = 0.704, Tmax = 0.746

9630 measured reflections
3028 independent reflections
2716 reflections with I > 2σ(I)
Rint = 0.037
θmax = 27.5°, θmin = 2.8°
h = −10→10
k = −32→32
l = −9→9

Refinement 

Refinement on F2

Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.042
wR(F2) = 0.089
S = 1.03
3028 reflections
173 parameters
2 restraints
Primary atom site location: structure-invariant 

direct methods
Secondary atom site location: difference Fourier 

map

Hydrogen site location: inferred from 
neighbouring sites

H-atom parameters constrained
w = 1/[σ2(Fo

2) + (0.0401P)2 + 1.2876P] 
where P = (Fo

2 + 2Fc
2)/3

(Δ/σ)max < 0.001
Δρmax = 0.39 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack x determined using 
1163 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et 
al., 2013)

Absolute structure parameter: 0.02 (3)

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data-2IUCrData (2019). 4, x191176    

Special details 

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. All hydrogen atoms were placed geometrically and refined using a riding-atom model approximation, with 
C—H = 0.95–1.00 Å, with Uiso(H) = 1.2Ueq(C). A rotating group model was used for the methyl groups.

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

x y z Uiso*/Ueq

S1 0.73168 (11) 0.55417 (3) 0.33500 (12) 0.01205 (19)
O1 0.7499 (3) 0.58926 (10) 0.1883 (4) 0.0159 (5)
O2 0.7908 (3) 0.49971 (10) 0.3513 (4) 0.0171 (6)
N1 0.8464 (4) 0.57903 (11) 0.5727 (4) 0.0138 (6)
H1 0.9279 0.5593 0.6732 0.017*
C1 0.7946 (5) 0.72772 (15) 0.5484 (6) 0.0188 (8)
C2 0.7594 (6) 0.73618 (15) 0.7189 (6) 0.0243 (9)
H2 0.7403 0.7715 0.7534 0.029*
C3 0.7522 (6) 0.69340 (15) 0.8383 (8) 0.0267 (9)
H3 0.7297 0.6994 0.9553 0.032*
C4 0.7781 (5) 0.64153 (15) 0.7865 (6) 0.0176 (8)
H4 0.7705 0.612 0.8661 0.021*
C5 0.8149 (4) 0.63297 (13) 0.6184 (5) 0.0134 (7)
C6 0.8256 (5) 0.67587 (14) 0.5006 (5) 0.0156 (7)
H6 0.8538 0.6699 0.388 0.019*
C7 0.7989 (5) 0.77163 (15) 0.4189 (6) 0.0216 (9)
C8 0.7988 (5) 0.80679 (16) 0.3081 (6) 0.0232 (9)
C9 0.7969 (7) 0.85150 (17) 0.1717 (8) 0.0345 (11)
H9A 0.8463 0.8393 0.0788 0.052*
H9B 0.8692 0.8811 0.26 0.052*
H9C 0.6741 0.8637 0.0855 0.052*
C10 0.5068 (4) 0.55427 (14) 0.2802 (5) 0.0138 (7)
C11 0.4331 (5) 0.50847 (14) 0.3182 (5) 0.0159 (7)
H11 0.5029 0.477 0.3718 0.019*
C12 0.2569 (5) 0.50936 (17) 0.2771 (6) 0.0207 (8)
H12 0.205 0.4782 0.3023 0.025*
C13 0.1549 (5) 0.55524 (16) 0.1993 (6) 0.0202 (8)
H13 0.0343 0.5557 0.1737 0.024*
C14 0.2302 (5) 0.60067 (15) 0.1587 (6) 0.0215 (8)
H14 0.1597 0.6319 0.1025 0.026*
C15 0.4069 (5) 0.60055 (14) 0.1997 (6) 0.0168 (7)
H15 0.4588 0.6315 0.1733 0.02*

Atomic displacement parameters (Å2) 

U11 U22 U33 U12 U13 U23

S1 0.0130 (4) 0.0114 (4) 0.0127 (4) 0.0013 (4) 0.0067 (3) −0.0001 (4)

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data-3IUCrData (2019). 4, x191176    

O1 0.0207 (14) 0.0150 (12) 0.0146 (12) 0.0001 (10) 0.0103 (11) 0.0000 (10)
O2 0.0190 (13) 0.0147 (12) 0.0183 (13) 0.0030 (10) 0.0094 (11) −0.0010 (10)
N1 0.0139 (15) 0.0131 (14) 0.0117 (14) 0.0025 (12) 0.0035 (12) 0.0011 (11)
C1 0.0196 (19) 0.0142 (17) 0.0189 (19) −0.0017 (15) 0.0057 (15) 0.0006 (15)
C2 0.037 (2) 0.0141 (19) 0.022 (2) 0.0016 (17) 0.0139 (19) −0.0035 (16)
C3 0.040 (3) 0.0230 (19) 0.0225 (19) 0.001 (2) 0.0188 (19) −0.002 (2)
C4 0.0222 (19) 0.0162 (18) 0.0174 (18) −0.0003 (15) 0.0119 (16) 0.0039 (15)
C5 0.0119 (17) 0.0106 (17) 0.0132 (17) −0.0002 (13) 0.0019 (14) −0.0016 (13)
C6 0.0148 (17) 0.0169 (18) 0.0140 (17) −0.0019 (14) 0.0058 (14) −0.0005 (14)
C7 0.026 (2) 0.0125 (19) 0.025 (2) −0.0011 (16) 0.0105 (17) −0.0060 (16)
C8 0.028 (2) 0.017 (2) 0.025 (2) −0.0021 (17) 0.0128 (19) −0.0025 (18)
C9 0.043 (3) 0.024 (2) 0.039 (3) 0.001 (2) 0.021 (2) 0.011 (2)
C10 0.0132 (15) 0.0171 (17) 0.0110 (16) 0.0015 (15) 0.0054 (14) −0.0030 (14)
C11 0.0180 (18) 0.0158 (18) 0.0129 (16) −0.0009 (15) 0.0062 (14) 0.0010 (14)
C12 0.0190 (19) 0.028 (2) 0.0158 (18) −0.0072 (16) 0.0088 (15) 0.0017 (16)
C13 0.0142 (18) 0.030 (2) 0.0172 (18) −0.0017 (17) 0.0078 (15) −0.0075 (17)
C14 0.0182 (19) 0.019 (2) 0.022 (2) 0.0015 (16) 0.0046 (16) −0.0051 (16)
C15 0.0194 (19) 0.0125 (17) 0.0168 (17) −0.0014 (14) 0.0069 (15) −0.0034 (14)

Geometric parameters (Å, º) 

S1—O1 1.427 (3) C7—C8 1.181 (5)
S1—O2 1.435 (3) C8—C9 1.477 (5)
S1—N1 1.636 (3) C9—H9A 0.98
S1—C10 1.756 (3) C9—H9B 0.98
N1—C5 1.440 (4) C9—H9C 0.98
N1—H1 0.88 C10—C11 1.388 (5)
C1—C6 1.394 (5) C10—C15 1.390 (5)
C1—C2 1.396 (6) C11—C12 1.380 (5)
C1—C7 1.445 (5) C11—H11 0.95
C2—C3 1.385 (6) C12—C13 1.387 (6)
C2—H2 0.95 C12—H12 0.95
C3—C4 1.392 (5) C13—C14 1.395 (5)
C3—H3 0.95 C13—H13 0.95
C4—C5 1.387 (5) C14—C15 1.384 (5)
C4—H4 0.95 C14—H14 0.95
C5—C6 1.390 (5) C15—H15 0.95
C6—H6 0.95

O1—S1—O2 119.34 (15) C8—C7—C1 178.1 (4)
O1—S1—N1 108.24 (15) C7—C8—C9 178.8 (4)
O2—S1—N1 104.96 (15) C8—C9—H9A 109.5
O1—S1—C10 108.01 (16) C8—C9—H9B 109.5
O2—S1—C10 108.67 (16) H9A—C9—H9B 109.5
N1—S1—C10 107.00 (15) C8—C9—H9C 109.5
C5—N1—S1 120.4 (2) H9A—C9—H9C 109.5
C5—N1—H1 119.8 H9B—C9—H9C 109.5
S1—N1—H1 119.8 C11—C10—C15 121.6 (3)

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data-4IUCrData (2019). 4, x191176    

C6—C1—C2 119.5 (3) C11—C10—S1 119.6 (3)
C6—C1—C7 119.1 (3) C15—C10—S1 118.8 (3)
C2—C1—C7 121.4 (3) C12—C11—C10 118.9 (3)
C3—C2—C1 120.4 (4) C12—C11—H11 120.5
C3—C2—H2 119.8 C10—C11—H11 120.5
C1—C2—H2 119.8 C11—C12—C13 120.6 (4)
C2—C3—C4 119.9 (4) C11—C12—H12 119.7
C2—C3—H3 120.1 C13—C12—H12 119.7
C4—C3—H3 120.1 C12—C13—C14 119.7 (3)
C5—C4—C3 119.9 (4) C12—C13—H13 120.1
C5—C4—H4 120.1 C14—C13—H13 120.1
C3—C4—H4 120.1 C15—C14—C13 120.4 (4)
C4—C5—C6 120.4 (3) C15—C14—H14 119.8
C4—C5—N1 118.6 (3) C13—C14—H14 119.8
C6—C5—N1 120.9 (3) C14—C15—C10 118.7 (3)
C5—C6—C1 119.8 (3) C14—C15—H15 120.7
C5—C6—H6 120.1 C10—C15—H15 120.7
C1—C6—H6 120.1

O1—S1—N1—C5 54.7 (3) O1—S1—C10—C11 148.8 (3)
O2—S1—N1—C5 −176.8 (3) O2—S1—C10—C11 18.0 (3)
C10—S1—N1—C5 −61.5 (3) N1—S1—C10—C11 −94.9 (3)
C6—C1—C2—C3 −1.1 (6) O1—S1—C10—C15 −31.3 (3)
C7—C1—C2—C3 178.6 (4) O2—S1—C10—C15 −162.1 (3)
C1—C2—C3—C4 −0.8 (6) N1—S1—C10—C15 85.0 (3)
C2—C3—C4—C5 1.4 (6) C15—C10—C11—C12 −0.7 (5)
C3—C4—C5—C6 −0.2 (5) S1—C10—C11—C12 179.1 (3)
C3—C4—C5—N1 178.1 (4) C10—C11—C12—C13 −0.1 (5)
S1—N1—C5—C4 126.3 (3) C11—C12—C13—C14 1.1 (6)
S1—N1—C5—C6 −55.4 (4) C12—C13—C14—C15 −1.3 (6)
C4—C5—C6—C1 −1.6 (5) C13—C14—C15—C10 0.5 (5)
N1—C5—C6—C1 −179.9 (3) C11—C10—C15—C14 0.5 (5)
C2—C1—C6—C5 2.3 (5) S1—C10—C15—C14 −179.3 (3)
C7—C1—C6—C5 −177.5 (3)

Hydrogen-bond geometry (Å, º) 

D—H···A D—H H···A D···A D—H···A

N1—H1···O2i 0.88 2.55 2.984 (4) 111
C4—H4···O1ii 0.95 2.45 3.256 (4) 143
C6—H6···O1 0.95 2.39 2.955 (4) 118

Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, y, z+1.

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