Crystal structure and Hirshfeld surface analysis of N,N′-[ethane-1,2-diylbis(­oxy)]bis­(4-methyl­benzene­sulfonamide)

Meral, S.; Kansiz, S.; Dege, N.; Alaman Agar, A.; Tsapyuk, G.G.

doi:10.1107/S2056989018017437

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ISSN: 2056-9890

Volume 75| Part 1| January 2019| Pages 81-85

https://doi.org/10.1107/S2056989018017437

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Crystal structure and Hirshfeld surface analysis of N,N′-[ethane-1,2-diylbis(oxy)]bis(4-methylbenzenesulfonamide)

Seher Meral,^a Sevgi Kansiz,^b Necmi Dege,^b Aysen Alaman Agar ^a and Galyna G. Tsapyuk ^c ^*

^aOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Chemistry, 55139, Samsun, Turkey, ^bOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Kurupelit, Samsun, Turkey, and ^cTaras Shevchenko National University of Kyiv, Department of Chemistry, 64, Vladimirska Str., Kiev 01601, Ukraine
^*Correspondence e-mail: tsapyuk@ukr.net

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 5 November 2018; accepted 10 December 2018; online 1 January 2019)

In the molecule of the title compound, C₁₆H₂₀N₂O₆S₂, the mid-point of the C—C bond of the central ethane moiety is located on a twofold rotation axis. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into supramolecular chains propagating along the [101] direction. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (43.1%), O⋯H/H⋯O (40.9%), C⋯H/H⋯C (8.8%) and C⋯C (5.5%) interactions.

Keywords: crystal structure; amine; benzenesulfonamide; Hirshfeld surface; hydrogen bonding.

CCDC reference: 1884045

1. Chemical context

Sulfonamides are synthetic molecules which include the SO₂–NH group and are called sulfa drugs. These effective drug molecules have an important role in the medical field, including as promising chemotherapeutic agents, and have been used in the treatment of many bacterial infections due to their physical, chemical and biological properties (Mahmood et al., 2016 ; Ghorab et al., 2018 ). Recently, sulfonamides have also been used in the organic synthesis reactions for the synthesis of linear or cyclic oligomers and the introduction of nucleophilic heteroatom functionality to the synthesized molecule (Ni et al., 2015 ). N,N′-ditosylalkane diamine is a disulfonamide synthesized by the tosylation of diamine, and this synthetic molecule has antibacterial properties (Alyar et al., 2011 ) and has also been used in many organic synthesis reactions (Rong et al., 1998 ). In this study, the synthesis, crystal structure and Hirshfeld surface analysis are reported for the new potential sulfa drug, N,N′-[ethane-1,2-diylbis(oxy)]bis(4-methylbenzenesulfonamide).

2. Structural commentary

The molecular structure of the title compound is illustrated in Fig. 1. The molecular point group symmetry is C_2v (mm2) (H atoms excluded), with the twofold rotation axis bisecting the central C1—C1ⁱ bond. The molecule is Z-shaped with the N1—S1—C2—C3 torsion angle being −60.6 (3)°. The C1—O1 bond length of 1.429 (3) Å and the O1—N1 bond length of 1.426 (2) Å are close to the values reported for similar compounds (see the Database survey). The S1—O2 and S1—O3 distances are 1.4376 (17) and 1.4168 (19) Å, respectively while the S1—N1 and S1—C2 distances are 1.647 (3) Å and 1.747 (3) Å, respectively.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 20% probability level. Symmetry code: (a) −x, y, −z − $[{1\over 2}]$ .

3. Supramolecular features

The crystal packing of the title compound features intermolecular N—H⋯O hydrogen bonds (Table 1 and Fig. 2), which connect the molecules into supramolecular chains propagating along the [101] direction. The chains are linked by pairs of C—H⋯O hydrogen bonds (Table 1, Fig. 3), forming a framework with small cavities of 99 Å³, ca 5% of the unit-cell volume.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.83 (3)	2.17 (3)	2.974 (3)	162 (3)
C1—H1A⋯O2ⁱⁱ	0.97	2.56	3.401 (4)	146
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Figure 2
A view of the chain structure formed by N—H⋯O hydrogen bonding.

Figure 3
A view along the b-axis of the crystal packing of the title compound. The hydrogen bonds (Table 1

) are shown as dashed lines.

4. Database survey

A search of the Cambridge Structural database (CSD, version 5.39, update May 2018; Groom et al., 2016 ) for structures similar to the title compound gave hits including 1S,2S,4S,5S)-2,5-bis[(p-toluenesulfonyl)amino]bicyclo(2.2.1)heptane (Berkessel et al., 2004 ), 1,6-anhydro-2,5-dideoxy-3,4-O-isopropylidene-2,5-bis[(4-methylbenzenesulfonyl)amino]-1-thiohexitol (Sureshkumar et al., 2005 ), (1R,3S)-1-(toluenesulfonylamido)-3-(toluenesulfonylamidomethyl)-3,5,5-trimethylcyclohexane (Berkessel et al., 2006 ) and N,N′-propylenedioxybis(2,4,6-tri-methylbenzenesulfonamide) (Wardell et al., 2004 ). In the latter compound, the C1—O1 bond length is 1.4448 (19) Å, in agreement with the value found in this study. In addition, the S1—O11 and S1—O12 distances are 1.4312 (12) and 1.4263 (13) Å, respectively and the S1—N1 and S1—C11distances are 1.6608 (14) and 1.7799 (16) Å, respectively.

5. Hirshfeld surface analysis

Hirshfeld surface analysis is a method for visualizing the interactions present in the crystal structure and providing quantitative information about them. The d_norm representation of the Hirshfeld surface reveals the close contacts of hydrogen-bond donors and acceptors, but other close contacts are also evident. The molecular Hirshfeld surfaces were generated using a standard (high) surface resolution with the three-dimensional d_norm surfaces mapped over a fixed colour scale of −0.464 (red) to 2.052 (blue) Å using the CrystalExplorer (Turner et al., 2017 ). The red spots on the surface indicate the intermolecular contacts involved in the hydrogen bonds. In Figs. 4 and 5, the identified red spot is attributed to the H⋯O close contacts which are due to the N—H⋯O hydrogen bonds (Table 1).

Figure 4
The Hirshfeld surface of the title compound mapped over d_norm, d_i and d_e.

Figure 5
Hirshfeld surface mapped over d_norm to visualize the intermolecular interactions in the title compound.

Fig. 6 shows the two-dimensional fingerprint of the sum of the contacts contributing to the Hirshfeld surface represented in normal mode. The second plot shown in Fig. 7 represents the O⋯H/H⋯O contacts (40.9%) between the oxygen atoms inside the surface and the hydrogen atoms outside the surface. d_e + d_i ∼2.0 Å and has two symmetrical points at the top, bottom left and right, which is characteristic of an N—H⋯O hydrogen bond.

Figure 6
The overall fingerprint plot for the title compound.

Figure 7
Two-dimensional fingerprint plots with a d_norm view of the H⋯H (43.1%), O⋯H/H⋯O (40.9%), C⋯H/H⋯C (8.8%) and C⋯C (5.5%) contacts in the title compound.

The H⋯H plot shown in Fig. 7 shows the two-dimensional fingerprint of the (d_i, d_e) points associated with hydrogen atoms. It is characterized by an end point that points to the origin and corresponds to d_i = d_e = 1.08 Å, which indicates the presence of the H⋯H contacts in this study (43.1%). The C⋯H/H⋯C plot in Fig. 7 shows the contact between the carbon atoms inside the surface and the hydrogen atoms outside the surface of Hirshfeld and vice versa. There are two symmetrical wings on the left and right sides (8.8%). Furthermore, there are C⋯C (5.5%), N⋯H/H⋯N (1.4%), O⋯C/C⋯O (0.1%) and S⋯H/H⋯S (0.1%) contacts in the title structure.

A view of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range −0.095 to 0.123 a.u. using the STO-3G basis set at the Hartree–Fock level of theory is shown in Fig. 8 where the N—H⋯O hydrogen-bond donors and acceptors are shown as blue and red areas around the atoms related with positive (hydrogen-bond donors) and negative (hydrogen-bond acceptors) electrostatic potentials, respectively.

Figure 8
A view of the three-dimensional Hirshfeld surface plotted over electrostatic potential energy.

6. Synthesis and crystallization

The title compound was synthesized according to the method of Bauer & Suresh (1963 ). Single crystals (m.p. 414–415 K) were obtained from an ethanol solution (yield 93%)

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. C-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding, with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms. The NH H atom was located in a difference-Fourier maps and freely refined.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₂₀N₂O₆S₂
M_r	400.46
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	16.3393 (18), 13.4977 (19), 9.7461 (11)
β (°)	113.442 (8)
V (Å³)	1972.0 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.30
Crystal size (mm)	0.56 × 0.36 × 0.13

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.873, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	6561, 1938, 1070
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.116, 0.90
No. of reflections	1938
No. of parameters	123
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.25
Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2002), SHELXL2017 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1884045

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018017437/xu5951sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018017437/xu5951Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018017437/xu5951Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: WinGX (Farrugia, 2012); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

N,N'-[Ethane-1,2-diylbis(oxy)]bis(4-methylbenzenesulfonamide) top

Crystal data top

C₁₆H₂₀N₂O₆S₂	F(000) = 840
M_r = 400.46	D_x = 1.349 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.3393 (18) Å	Cell parameters from 6407 reflections
b = 13.4977 (19) Å	θ = 2.0–27.2°
c = 9.7461 (11) Å	µ = 0.30 mm⁻¹
β = 113.442 (8)°	T = 296 K
V = 1972.0 (4) Å³	Prism, colorless
Z = 4	0.56 × 0.36 × 0.13 mm

Data collection top

Stoe IPDS 2 diffractometer	1938 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1070 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.086
rotation method scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −20→20
T_min = 0.873, T_max = 0.973	k = −16→16
6561 measured reflections	l = −12→9

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0562P)²] where P = (F_o² + 2F_c²)/3
S = 0.90	(Δ/σ)_max < 0.001
1938 reflections	Δρ_max = 0.14 e Å⁻³
123 parameters	Δρ_min = −0.25 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
S1	0.19812 (4)	0.13241 (6)	0.11223 (9)	0.0759 (3)
O1	0.04273 (10)	0.15963 (13)	−0.0863 (2)	0.0722 (5)
C1	0.00029 (17)	0.0748 (2)	−0.1731 (3)	0.0698 (7)
H1A	−0.060770	0.071765	−0.181199	0.084*
H1B	0.030688	0.015643	−0.121023	0.084*
O3	0.28617 (11)	0.15543 (15)	0.1220 (3)	0.0907 (7)
O2	0.17825 (13)	0.03371 (14)	0.1379 (3)	0.0928 (7)
N1	0.13462 (14)	0.1594 (2)	−0.0629 (3)	0.0751 (7)
C2	0.16891 (16)	0.2121 (2)	0.2267 (3)	0.0705 (8)
C5	0.1182 (2)	0.3366 (3)	0.4043 (4)	0.0929 (10)
C7	0.1370 (2)	0.1733 (3)	0.3271 (4)	0.1030 (11)
H7	0.131947	0.105133	0.335264	0.124*
C4	0.1518 (2)	0.3736 (3)	0.3067 (4)	0.1041 (11)
H4	0.157573	0.441748	0.299978	0.125*
C6	0.1129 (3)	0.2367 (4)	0.4145 (5)	0.1153 (13)
H6	0.092328	0.210422	0.483059	0.138*
C3	0.1774 (2)	0.3119 (3)	0.2180 (4)	0.0954 (10)
H3	0.200335	0.338428	0.152627	0.115*
C8	0.0890 (3)	0.4066 (4)	0.4973 (5)	0.1375 (16)
H8A	0.083016	0.370639	0.577813	0.206*
H8B	0.032607	0.435597	0.435712	0.206*
H8C	0.132692	0.457942	0.537350	0.206*
H1	0.146 (2)	0.217 (2)	−0.080 (4)	0.089 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0600 (4)	0.0881 (5)	0.0859 (6)	−0.0056 (4)	0.0356 (4)	0.0138 (4)
O1	0.0565 (9)	0.0901 (13)	0.0773 (13)	−0.0033 (9)	0.0344 (9)	−0.0099 (10)
C1	0.0658 (14)	0.0790 (17)	0.0728 (19)	−0.0063 (14)	0.0365 (15)	0.0007 (16)
O3	0.0572 (11)	0.1173 (16)	0.1016 (17)	−0.0056 (10)	0.0358 (11)	0.0226 (13)
O2	0.0875 (13)	0.0809 (13)	0.1204 (19)	−0.0012 (10)	0.0523 (13)	0.0201 (13)
N1	0.0571 (13)	0.0913 (19)	0.0849 (19)	−0.0072 (12)	0.0367 (12)	0.0028 (15)
C2	0.0576 (14)	0.084 (2)	0.0694 (19)	−0.0124 (13)	0.0251 (13)	0.0098 (15)
C5	0.0732 (19)	0.131 (3)	0.065 (2)	−0.008 (2)	0.0175 (16)	−0.010 (2)
C7	0.122 (3)	0.108 (2)	0.100 (3)	−0.038 (2)	0.066 (2)	0.000 (2)
C4	0.124 (3)	0.089 (2)	0.100 (3)	−0.008 (2)	0.044 (2)	0.000 (2)
C6	0.127 (3)	0.148 (4)	0.097 (3)	−0.040 (3)	0.071 (3)	−0.014 (3)
C3	0.107 (2)	0.094 (2)	0.101 (3)	−0.0100 (18)	0.059 (2)	0.011 (2)
C8	0.123 (3)	0.192 (4)	0.093 (3)	0.006 (3)	0.038 (2)	−0.044 (3)

Geometric parameters (Å, º) top

S1—O2	1.4168 (19)	C5—C6	1.357 (5)
S1—O3	1.4376 (17)	C5—C4	1.368 (5)
S1—N1	1.647 (3)	C5—C8	1.512 (5)
S1—C2	1.747 (3)	C7—C6	1.371 (5)
O1—N1	1.426 (2)	C7—H7	0.9300
O1—C1	1.429 (3)	C4—C3	1.379 (5)
C1—C1ⁱ	1.494 (5)	C4—H4	0.9300
C1—H1A	0.9700	C6—H6	0.9300
C1—H1B	0.9700	C3—H3	0.9300
N1—H1	0.83 (3)	C8—H8A	0.9600
C2—C3	1.361 (4)	C8—H8B	0.9600
C2—C7	1.381 (4)	C8—H8C	0.9600

O2—S1—O3	119.02 (12)	C6—C5—C8	122.2 (4)
O2—S1—N1	107.29 (15)	C4—C5—C8	120.0 (4)
O3—S1—N1	102.83 (12)	C6—C7—C2	119.1 (3)
O2—S1—C2	109.02 (13)	C6—C7—H7	120.5
O3—S1—C2	110.20 (13)	C2—C7—H7	120.5
N1—S1—C2	107.80 (13)	C5—C4—C3	121.4 (3)
N1—O1—C1	108.99 (19)	C5—C4—H4	119.3
O1—C1—C1ⁱ	113.68 (15)	C3—C4—H4	119.3
O1—C1—H1A	108.8	C5—C6—C7	122.2 (3)
C1ⁱ—C1—H1A	108.8	C5—C6—H6	118.9
O1—C1—H1B	108.8	C7—C6—H6	118.9
C1ⁱ—C1—H1B	108.8	C2—C3—C4	119.7 (3)
H1A—C1—H1B	107.7	C2—C3—H3	120.2
O1—N1—S1	110.82 (17)	C4—C3—H3	120.2
O1—N1—H1	106 (2)	C5—C8—H8A	109.5
S1—N1—H1	108 (2)	C5—C8—H8B	109.5
C3—C2—C7	119.7 (3)	H8A—C8—H8B	109.5
C3—C2—S1	120.6 (2)	C5—C8—H8C	109.5
C7—C2—S1	119.7 (3)	H8A—C8—H8C	109.5
C6—C5—C4	117.9 (3)	H8B—C8—H8C	109.5

N1—O1—C1—C1ⁱ	−63.7 (3)	C3—C2—C7—C6	1.2 (5)
C1—O1—N1—S1	−108.3 (2)	S1—C2—C7—C6	−178.9 (3)
O2—S1—N1—O1	65.1 (2)	C6—C5—C4—C3	1.8 (6)
O3—S1—N1—O1	−168.64 (18)	C8—C5—C4—C3	−178.7 (3)
C2—S1—N1—O1	−52.2 (2)	C4—C5—C6—C7	−2.4 (6)
O2—S1—C2—C3	−176.8 (3)	C8—C5—C6—C7	178.1 (3)
O3—S1—C2—C3	50.9 (3)	C2—C7—C6—C5	0.9 (6)
N1—S1—C2—C3	−60.6 (3)	C7—C2—C3—C4	−1.7 (5)
O2—S1—C2—C7	3.3 (3)	S1—C2—C3—C4	178.4 (3)
O3—S1—C2—C7	−129.0 (2)	C5—C4—C3—C2	0.2 (6)
N1—S1—C2—C7	119.5 (3)

Symmetry code: (i) −x, y, −z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱⁱ	0.83 (3)	2.17 (3)	2.974 (3)	162 (3)
C1—H1A···O2ⁱⁱⁱ	0.97	2.56	3.401 (4)	146

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

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