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Crystal Structure of 4-(4-Aminophenylsulfonyl)Benzenamine

Dileep CS1*, Mallesha L2 and Sridhar MA1

1Department of Studies in Physics, University of Mysore, Manasagangotri, Mysore 570 006, India

2PG Department of Chemistry, JSS College of Arts, Commerce and Science, Ooty Road, Mysore-25, India

Corresponding Author:

Dileep CS
Department of Studies in Physics
University of Mysore
Manasagangotri, Mysore 570 006, India
Tel: 0821-2419361
E-mail: [email protected]

Received date: September 18, 2013; Accepted date: September 20, 2013; Published date: December 28, 2013

Citation: Dileep CS, Mallesha L, Sridhar MA (2013) Crystal Structure of 4-(4-Aminophenylsulfonyl)Benzenamine. Chem Sci J 4:077. doi:10.4172/2150-3494.1000077

Copyright: © 2013 Dileep CS, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

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Keywords

4-(4-Aminophenylsulfonyl)aniline; Crystal structure; Weak interaction

Introduction

Dapsone is a white crystalline powder, used in combination with pyrimethamine in the treatment of malaria [1]. It is a very weak Lewis base which finds use as a leprostatic drug [2]. Dapsone is 4-(4-aminophenylsulfonyl)aniline, which has a chemical structure very similar to sulfonamines. Like sulfonamines, its antibacterial property is due to inhibiting folic acid synthesis. Although it is most often used in multidrug therapy, it has numerous other applications. As an anti-infective agent, it is also utilized in the treatment of malaria and Pneumocystis cariniipneumonia. In dermatology, it has been found helpful in the treatment of numerous non-infectious, inflammatory, autoimmune and bullous diseases [3]. The structure of the Dapsone 0.33 hydrate is known [4] but salts or adducts of this compound are not common. Crystal structure of 4-(4-Aminophenylsulfonyl) aniline-1,3,5-trinitrobenzene has been reported [5]. A series of Schiff base and 2-azetidinones of 4, 4’-diaminodiphenylsulphone has been reported [6]. 4, 4’-Diaminodiphenylsulphone, a sulphone analog have been proved to be a powerful antimicrobial agent [7]. Reactions of chlorodinitro and dichlorodinitrobenzofuroxans with 4-[(4-aminophenyl)sulfonyl]aniline has been reported [8]. In the present study, 4-(4-aminophenylsulfonyl)benzenamine (1) have been prepared and their crystal structure has been determined by singlecrystal X-ray diffraction.

Methods

Physical measurements

All solvents and reagents were purchased from Merck Chemicals, India. 4,4’-Dinitrodiphenyl sulfide was oxidized to the sulfone in a solution of potassium dichromate, glacial acetic acid, and sulfuric acid. The nitro- groups on the sulfone were reduced with tin and concentrated hydrochloric acid, and the free base obtained by treatment with an alkali. The purity of the compound (1) is confirmed by the TLC. A little quantity of compound was taken again for recrystallization to get a pure crystal.

Structure determination and refinement

X-ray data for 1 (0.30 × 0.20 × 0.20 mm) was collected with Bruker axis kappa apex2 CCD Diffractometer using CrysAlisPro software, graphite monochromatic MoKα radiation (λ = 0.71073 Å) at 293 K. The structure was solved by direct methods using SHELXS97 [9] and all of the non-hydrogen atoms were refined anisotropically by full-matrix least-squares on F2 using SHELXL97 [9]. The hydrogen atoms were placed in their calculated positions and included in the refinement using the riding model. Absorption correction was applied using CrysAlis RED and all calculations were performed using SHELXTL [10]. A scheme for the molecular structure of 1 is shown in Figure 1.

chemical-sciences-journal-benzenamine

Figure 1: Molecular structure of 4-(4-Aminophenylsulfonyl) benzenamine.

Results and Discussion

Crystals of 1 suitable for single crystal X-ray diffraction measurements were grown by slow evaporation of methanol. Compound 1 (Figure 2) crystallizes in monoclinic cell (space group C2/c). Crystal data, data collection and structure refinement details for 1 is listed in Table 1.

Empirical formula C36H36N6O7S3
Formula weight 760.89
Temperature 293(2) K
Wavelength 0.71073Å
Reflns.  for cell determination 5857
θ range for above 2.50°-27.78°
Crystal system Monoclinic
Space group C2/c
Cell dimensions  
a = 49.0067(12) Å, b = 11.4239(3) Å, c = 13.0995(3) Å
α = 90°,   β = 92.6100(10)°,   γ = 90°
Volume 7326.1(3) Å3
Z 8
Density(calculated) 1.380 Mg/m3
Absorption coefficient 0.260 mm-1
F000 3184
  Crystal size 0.30 × 0.20 × 0.20 mm
Theta range for data collection 2.18°   to 25.00°
Index ranges -58  ≤ h  ≤  58
  0  ≤  k  ≤ 13
  0  ≤ l ≤ 15
Reflections collected 6464
Independent reflections 6464 [R(int) = 0.0000]
Absorption correction Semi-empirical from equivalents
Max.  and min.  transmission 0.9499 and 0.9262
Refinement method Full-matrix least-squares on F2  
Data / restraints / parameters 6464 / 6 / 469
Goodness-of- fit on F 2 1.777
Final R indices [I > 2 (I)] R1 = 0.0390, wR2 = 0.1137
R indices (all data) R1 = 0.0478, wR2 = 0.1176
Largest diff.  peak and hole 0.259 and -0.341 e.Å3

Table 1: Crystal data and structure refinement for 4-(4-aminophenylsulfonyl) benzenamine.

chemical-sciences-journal-diagram

Figure 2: ORTEP diagram of 4-(4-aminophenylsulfonyl) benzenamine.

The bond lengths and angles involving the non-hydrogen atoms are given in Tables 2 and 3. Bond lengths and angles in the title compound have normal values [11] and are comparable with the similar crystal structure [12]. The position of S8A, S8B and S8C atoms are distorted trigonal planar geometry as indicated by bond angle values (O9AS8A- 010A) = 118.14(10)°, (O9B-S8B-O10B) =117.74(11)°, (O9C-S8CO10C) = 117.91(9)°. The bond length of S8A-C5A = 1.7354(19) Å, S8AC11A = 1.7535(18) Å, S8B-C5B = 1.7443(19) Å, S8B-C11B = 1.743(2) Å and S8C-C5C = 1.753(2) Å, S8C-C11C = 1.742(2) Å, is comparable with bond length of 1.758(4) Å and 1.760(4) Å for compound reported earlier [13]. The structure exhibits both inter and intermolecular hydrogen bonds of the type N–H••O, N–H••N, and C–H••O. with symmetry codes 1/2-x, 1/2+y, 1/2-z, x, 1-y, -1/2+z, x, y, -1+z and the intramolecular hydrogen bond is C–H••O. Packing of the molecule (1) along a-axis is shown in Figure 3.

chemical-sciences-journal-molecule

Figure 3: Packing of the molecule (1) along a-axis.

Atom Length Atom Length
N1A-C2A 1.367(3) S8B-O10B 1.4435(17)
C2A-C7A 1.387(3) S8B-C11B 1.7430(19)
C2A-C3A 1.398(3) C11B-C12B 1.381(3)
C3A-C4A 1.360(3) C11B-C16B 1.384(3)
C4A-C5A 1.388(3) C12B-C13B 1.364(3)
C5A-C6A 1.395(3) C13B-C14B 1.381(3)
C5A-S8A 1.735(2) C14B-N17B 1.358(3)
C6A-C7A 1.365(3) C14B-C15B 1.398(3)
S8A-O10A 1.4339(15) C15B-C16B 1.361(3)
S8A-O9A 1.4400(15) N1C-C2C 1.374(3)
S8A-C11A 1.7534(18) C2C-C7C 1.389(3)
C11A-C16A 1.384(3) C2C-C3C 1.393(3)
C11A-C12A 1.380(3) C3C-C4C 1.377(3)
C12A-C13A 1.373(3) C4C-C5C 1.381(3)
C13A-C14A 1.388(3) C5C-C6C 1.391(3)
C14A-N17A 1.378(2) C5C-S8C 1.752(2)
C14A-C15A 1.393(3) C6C-C7C 1.364(3)
C15A-C16A 1.362(3) S8C-O9C 1.4380(15)
N1B-C2B 1.364(3) S8C-O10C 1.4422(15)
C2B-C7B 1.392(3) S8C-C11C 1.7421(19)
C2B-C3B 1.386(3) C11C-C12C 1.385(3)
C3B-C4B 1.366(3) C11C-C16C 1.382(2)
C4B-C5B 1.385(3) C12C-C13C 1.369(3)
C5B-C6B 1.380(3) C13C-C14C 1.387(3)
C5B-S8B 1.744(2) C14C-N17C 1.364(2)
C6B-C7B 1.371(3) C14C-C15C 1.394(3)
S8B-O9B 1.4418(17) C15C-C16C 1.360(3)
N1A-H1A1 0.8600 C12B-H12B 0.9300
N1A-H1A2 0.8600 C13B-H13B 0.9300
C3A-H3A 0.9300 C15B-H15B 0.9300
C4A-H4A 0.9300 C16B-H16B 0.9300
C6A-H6A 0.9300 N17B-H17C 0.8600
C7A-H7A 0.9300 N17B-H17D 0.8600
C12A-H12A 0.9300 N1C-H1C1 0.8600
C13A-H13A 0.9300 N1C-H1C2 0.8600
C15A-H15A 0.9300 C3C-H3C 0.9300
C16A-H16A 0.9300 C4C-H4C 0.9300
N17A-H17A 0.8600 C6C-H6C 0.9300
N17A-H17B 0.8600 C7C-H7C 0.9300
N1B-H1B1 0.8600 C12C-H12C 0.9300
N1B-H1B2 0.8600 C13C-H13C 0.9300
C3B-H3B 0.9300 C15C-H15C 0.9300
C4B-H4B 0.9300 C16C-H16C 0.9300
C6B-H6B 0.9300 N17C-H17E 0.8600
C7B-H7B 0.9300 N17C-H17F 0.8600

Table 2: Bond Lengths (Å) of 4-(4-aminophenylsulfonyl) benzenamine.

Atoms Angle Atoms Angle
N1A-C2A-C7A 120.3(2) O9B-S8B-C11B 107.69(10)
N1A-C2A-C3A 121.6(2) O10B-S8B-C11B 108.76(10)
C7A-C2A-C3A 118.08(19) C5B-S8B-C11B 105.39(9)
C4A-C3A-C2A 121.2(2) C12B-C11B-C16B 119.72(18)
C3A-C4A-C5A 120.18(18) C12B-C11B-S8B 119.58(16)
C4A-C5A-C6A 119.33(18) C16B-C11B-S8B 120.62(15)
C4A-C5A-S8A 120.60(14) C13B-C12B-C11B 119.68(19)
C6A-C5A-S8A 120.07(15) C14B-C13B-C12B 121.64(18)
C7A-C6A-C5A 119.9(2) C13B-C14B-N17B 120.80(18)
C6A-C7A-C2A 121.3(2) C13B-C14B-C15B 117.93(18)
O10A-S8A-O9A 118.14(10) N17B-C14B-C15B 121.26(19)
O10A-S8A-C5A 107.80(10) C16B-C15B-C14B 120.81(18)
O9A-S8A-C5A 108.24(9) C15B-C16B-C11B 120.20(18)
O10A-S8A-C11A 107.25(9) N1C-C2C-C7C 121.3(2)
O9A-S8A-C11A 107.80(9) N1C-C2C-C3C 120.7(2)
C5A-S8A-C11A 107.14(8) C7C-C2C-C3C 118.0(2)
C16A-C11A-C12A 119.40(17) C4C-C3C-C2C 120.9(2)
C16A-C11A-S8A 119.32(14) C3C-C4C-C5C 120.2(2)
C12A-C11A-S8A 121.27(14) C6C-C5C-C4C 119.2(2)
C13A-C12A-C11A 120.22(18) C6C-C5C-S8C 120.23(16)
C14A-C13A-C12A 120.55(18) C4C-C5C-S8C 120.54(17)
C13A-C14A-N17A 120.49(17) C5C-C6C-C7C 120.3(2)
C13A-C14A-C15A 118.73(17) C6C-C7C-C2C 121.4(2)
N17A-C14A-C15A 120.76(18) O9C-S8C-O10C 117.90(10)
C16A-C15A-C14A 120.42(18) O9C-S8C-C11C 108.44(9)
C15A-C16A-C11A 120.67(18) O10C-S8C-C11C 108.34(9)
N1B-C2B-C7B 120.0(2) O9C-S8C-C5C 107.22(10)
N1B-C2B-C3B 121.2(2) O10C-S8C-C5C 107.91(9)
C7B-C2B-C3B 118.83(19) C11C-S8C-C5C 106.48(9)
C4B-C3B-C2B 120.79(19) C12C-C11C-C16C 119.51(18)
C3B-C4B-C5B 120.04(19) C12C-C11C-S8C 120.90(15)
C4B-C5B-C6B 119.73(19) C16C-C11C-S8C 119.52(15)
C4B-C5B-S8B 119.69(16) C11C-C12C-C13C 119.99(19)
C6B-C5B-S8B 120.28(15) C14C-C13C-C12C 120.96(19)
C7B-C6B-C5B 120.22(18) N17C-C14C-C13C 121.84(19)
C6B-C7B-C2B 120.4(2) N17C-C14C-C15C 119.93(18)
O9B-S8B-O10B 117.72(11) C13C-C14C-C15C 118.22(18)
O9B-S8B-C5B 109.33(10) C16C-C15C-C14C 120.95(18)
O10B-S8B-C5B 107.28(10) C15C-C16C-C11C 120.34(18)
C2A-N1A-H1A1 120.0 C13B-C12B-H12B 120.2
C2A-N1A-H1A2 120.0 C11B-C12B-H12B 120.2
H1A1-N1A-H1A2 120.0 C14B-C13B-H13B 119.2
C4A-C3A-H3A 119.4 C12B-C13B-H13B 119.2
C2A-C3A-H3A 119.4 C16B-C15B-H15B 119.6
C3A-C4A-H4A 119.9 C14B-C15B-H15B 119.6
C5A-C4A-H4A 119.9 C15B-C16B-H16B 119.9
C7A-C6A-H6A 120.1 C11B-C16B-H16B 119.9
C5A-C6A-H6A 120.1 C14B-N17B-H17C 120.0
C6A-C7A-H7A 119.3 C14B-N17B-H17D 120.0
C2A-C7A-H7A 119.3 H17C-N17B-H17D 120.0
C13A-C12A-H12A 119.9 C2C-N1C-H1C1 120.0
C11A-C12A-H12A 119.9 C2C-N1C-H1C2 120.0
C14A-C13A-H13A 119.7 H1C1-N1C-H1C2 120.0
C12A-C13A-H13A 119.7 C4C-C3C-H3C 119.5
C16A-C15A-H15A 119.8 C2C-C3C-H3C 119.5
C14A-C15A-H15A 119.8 C3C-C4C-H4C 119.9
C15A-C16A-H16A 119.7 C5C-C4C-H4C 119.9
C11A-C16A-H16A 119.7 C5C-C6C-H6C 119.9
C14A-N17A-H17A 120.0 C7C-C6C-H6C 119.9
C14A-N17A-H17B 120.0 C6C-C7C-H7C 119.3
H17A-N17A-H17B 120.0 C2C-C7C-H7C 119.3
C2B-N1B-H1B1 120.0 C11C-C12C-H12C 120.0
C2B-N1B-H1B2 120.0 C13C-C12C-H12C 120.0
H1B1-N1B-H1B2 120.0 C14C-C13C-H13C 119.5
C4B-C3B-H3B 119.6 C12C-C13C-H13C 119.5
C2B-C3B-H3B 119.6 C16C-C15C-H15C 119.5
C3B-C4B-H4B 120.0 C14C-C15C-H15C 119.5
C5B-C4B-H4B 120.0 C15C-C16C-H16C 119.8
C7B-C6B-H6B 119.9 C11C-C16C-H16C 119.8
C5B-C6B-H6B 119.9 C14C-N17C-H17E 120.0
C6B-C7B-H7B 119.8 C14C-N17C-H17F 120.0
C2B-C7B-H7B 119.8 H17E-N17C-H17F 120.0

Table 3: Bond Angles (°) of 4-(4-aminophenylsulfonyl) benzenamine.

Conclusion

In summary, 4-(4-aminophenylsulfonyl)benzenamine (1) was prepared and their structure was confirmed by single crystal X-ray diffraction. In compound 1, the molecular packing is stabilized by intermolecular hydrogen bonds of the type N–H••O, N–H••N, and C–H••O. with symmetry codes 1/2-x, 1/2+y, 1/2-z, x, 1-y, -1/2+z, x, y, -1+z and the intramolecular hydrogen bond is C–H••O.

Competing Interests

The authors declare that they have no competing interests.

Authors Contributions

LM carried out the recrystalization work. CSD and MAS interpreted the data and were involved in the preparation of manuscript.

Acknowledgement

LM thanks the JSS College of Arts, Commerce and Science for use of their research facilities. CSD would like to acknowledge the UGC–BRS and the University of Mysore for financial assistance.

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