Home Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S
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Crystal structure of (E)-N′-((4-aminophenyl)sulfonyl)-N,N-dimethylformimidamide, C9H13N3O2S

  • Alaa A.-M. Abdel-Aziz ORCID logo EMAIL logo , Adel S. El-Azab , Hazem A. Ghabbour and Ahmad J. Obaidullaha
Published/Copyright: December 5, 2019

Abstract

C9H13N3O2S, monoclinic, P21/c (no. 14), a = 8.0984(4) Å, b = 17.3203(10) Å, c = 9.6802(4) Å, β = 124.031(3)°, V = 1125.26(10) Å3, Z = 4, Rgt(F) = 0.0504, wRref(F2) = 0.1275, T = 293(2) K.

CCDC no.: 1514612

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Colourless needle
Size:0.59 × 0.13 × 0.09 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.27 mm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
θmax, completeness:27.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:16215, 2581, 0.066
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 1884
N(param)refined:138
Programs:SHELX [1], Bruker [2]
Table 2:

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

AtomxyzUiso*/Ueq
S10.31663(8)−0.59517(3)−0.17899(7)0.03732(19)
O10.4058(3)−0.64624(11)−0.0384(2)0.0635(5)
O20.2455(2)−0.52250(9)−0.1591(2)0.0490(5)
N10.4747(3)−0.58306(11)−0.2299(3)0.0449(5)
N20.6689(4)−0.49539(14)−0.2558(3)0.0610(6)
N3−0.3860(3)−0.74972(13)−0.7473(3)0.0613(7)
H2−0.4202−0.7928−0.73110.074*
H3−0.4502−0.7290−0.84010.074*
C10.0513(4)−0.71410(13)−0.3266(3)0.0438(6)
H1A0.1191−0.7371−0.22190.053*
C2−0.1152(4)−0.74905(13)−0.4584(3)0.0472(6)
H2A−0.1592−0.7955−0.44170.057*
C3−0.2195(3)−0.71587(12)−0.6171(3)0.0388(5)
C4−0.1487(3)−0.64599(12)−0.6387(3)0.0363(5)
H4A−0.2143−0.6232−0.74360.044*
C50.0161(3)−0.61130(12)−0.5066(3)0.0344(5)
H5A0.0602−0.5646−0.52240.041*
C60.1189(3)−0.64450(12)−0.3492(3)0.0329(5)
C70.5336(4)−0.51297(15)−0.2254(3)0.0471(6)
H10.4779−0.4732−0.19970.057*
C80.7321(7)−0.4158(2)−0.2474(7)0.1030(14)
H8A0.6694−0.3832−0.20940.154*
H8B0.6943−0.3993−0.35610.154*
H8C0.8742−0.4124−0.17130.154*
C90.7652(5)−0.5543(2)−0.2925(5)0.0894(12)
H9A0.7915−0.5985−0.22340.134*
H9B0.8883−0.5345−0.27080.134*
H9C0.6797−0.5688−0.40760.134*

Source of material

A mixture of benzenesulfonamide (344 mg, 2 mmol) and N,N-dimethylformamide dimethyl acetal (476 mg, 4 mmol) in ethanol (10 mL) was heated under reflux for 10 h. The reaction mixture was cooled and the separated solid was filtered, dried and recrystallized from ethanol. Yield 96%; 1H NMR (DMSO-d6; 500 MHz): δ 8.10 (s, 1H, N—C(H)=N), 7.39–7.37 (d, 2H, J = 8.5 Hz, Ar—H), 6.58–6.56 (d, 2H, J = 9.0 Hz, Ar—H), 5.82 (s, 2H, NH2), 3.10 (s, 3H, CH3), 2.87 (s, 3H, CH3) ppm; 13C NMR (DMSO-d6; 125 MHz): δ 35.30 (CH3), 41.14 (CH3), 113.01, 128.20, 129.03, 152.41, 159.43 (N—CH=N) ppm; MS: m/z = 227.1.

Experimental details

Cell refinement and data reduction were carried out by Bruker SAINT, SHELXT [1], [2].

Comment

Benzenesulfonamides (ArSO2NH2) incorporating aromatic and heterocyclic ring systems are an important group of compounds, which have a wide range of biological activity such as anti-inflammatory, COX-1/2 inhibiting activity, inhibitors of the metalloenzyme carbonic anhydrase, and antitumor activities [3], [4], [5], [6], [7], [8]. Recently, the synthesis of N-sulfonylformamidines has been reported through condensation of formamides and versatile sulfonamides using thionylchloride in the presence of chloroform as solvent [9]. The title compound was synthesized and reported according to method described by Silva, et al. [10]. Detailed synthetic studies indicate that this procedure gives the title compound.

The asymmetric unit of the title compound contains one independent molecule. The bond length between N1—C7 is 1.296(3) Å which indicates that it is a double bond, compared to 1.320(3) Å between N2—C7. Bond lengths and angles of the title molecule are in the expected ranges [11]. The molecules pack in the crystal structure via two strong classical intermolecular hydrogen bonds, N3—H2⋯N1i and N3—H3⋯O1ii in addition to one non-classical hydrogen bond C9—H9B⋯O2iii. The H⋯A distances are 2.31, 2.14 and 2.47 Å, respectively and the angles are 170, 164 and 161°, respectively. Symmetry codes: (i) x − 1, −y − 3/2, z − 1/2; (ii) x − 1, y, z − 1; (iii) x + 1, y, z.

Acknowledgements

The authors acknowledge financial support from the Researchers Supporting Project number (RSP-2019/40), King Saud University, Riyadh Saudi Arabia.

References

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Received: 2019-10-20
Accepted: 2019-11-11
Published Online: 2019-12-05
Published in Print: 2020-02-25

©2019 Alaa A.-M. Abdel-Aziz et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 Public License.

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  73. Crystal structure of (E)-3-(3-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-1-phenyl-1H-pyrazol-4-yl)-1-phenylprop-2-en-1-one, C27H21N5O
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  75. Crystal structure of η6-p-cymene-iodido-(N-isopropyl-1-(pyridin-2-yl)methanimine-κ2N,N′)ruthenium(II) hexafluorophosphate(V), C19H26IN2F6Ru
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  77. Low temperature redetermination of the crystal structure of catena-poly[[tri-4-fluorobenzyltin(IV)]μ2-pyridine-4-carboxylato-κ2N:O], {C27H22F3NO2Sn}n
  78. Crystal structure of bis(2-propyl-1H-benzo[d]imidazol-3-ium) tetrachloridozincate(II), C10H13Cl4N2Zn
  79. The crystal structure of (Z)-3-hydrazono-5-nitroindolin-2-one – dimethyl sulfoxide (1/1), C8H6N4O3
  80. Crystal structure of bis-[N-(1-pyrazin-2-yl-ethylidene)-cyanoacetic acid-hydrazonato-κ3O,N,N′)]-zinc(II), C18H16N10O2Zn
  81. Crystal structure and photochromism of 1-(2,5-dimethyl-3-thienyl)-2-[2-methyl-5-(benzaldoxime)-3-thienyl] perfluorocyclopentene, C23H17F6NOS2
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