Literature DB >> 21577505

4-(Benzyl-ideneamino)benzene-sulfonamide.

Bradley T Loughrey1, Michael L Williams, Peter C Healy.   

Abstract

The title compound, C(13)H(12)N(2)O(2)S, formed by Schiff base condensation of benzaldehyde with sulfanilamide, crystallizes as discrete mol-ecular species linked by N-H⋯N and N-H⋯O hydrogen bonds between the sulfamide nitro-gen H atoms and the aza-methine N and one sulfamide O atom, respectively, forming a two-dimensional array in the bc plane. The aza-methine group is rotated slightly out of the benzaldehyde benzene plane [C-C-C-N torsion angle = 8.1 (3)°], while the dihedral angle between the two benzene rings is 30.0 (1)°.

Entities:  

Year:  2009        PMID： 21577505      PMCID： PMC2970159          DOI： 10.1107/S1600536809030256

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

Condensation of substituted benzaldehydes with sulfanilamide yields a diverse array of Schiff bases which display inter­esting enzymatic inhibition, see Supuran et al. (1996 ▶); Lin et al. (2008 ▶). For our ongoing studies on the synthesis, structures and biological activity of organometallic Cp*Ru(II) arene complexes Loughrey et al. (2008 ▶, 2009 ▶). For related structures, see Chumakov et al. (2006 ▶); Subashini et al. (2009 ▶).

Experimental

Crystal data

C13H12N2O2S M = 260.32 Monoclinic, a = 14.5206 (8) Å b = 11.4992 (6) Å c = 7.7846 (5) Å β = 103.287 (6)° V = 1265.04 (13) Å3 Z = 4 Mo Kα radiation μ = 0.25 mm−1 T = 296 K 0.43 × 0.31 × 0.20 mm

Data collection

Oxford-Diffraction Gemini S Ultra diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.900, T max = 0.952 8991 measured reflections 2253 independent reflections 1928 reflections with I > 2σ(I) R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.085 S = 1.05 2253 reflections 163 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.24 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030256/tk2519sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030256/tk2519Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H12N2O2SF(000) = 544
Mr = 260.32Dx = 1.367 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 6065 reflections
a = 14.5206 (8) Åθ = 3.2–32.1°
b = 11.4992 (6) ŵ = 0.25 mm−1
c = 7.7846 (5) ÅT = 296 K
β = 103.287 (6)°Block, colourless
V = 1265.04 (13) Å30.43 × 0.31 × 0.20 mm
Z = 4
Oxford-Diffraction Gemini S Ultra diffractometer2253 independent reflections
Radiation source: Enhance (Mo) X-ray Source1928 reflections with I > 2σ(I)
graphiteRint = 0.018
Detector resolution: 16.0774 pixels mm-1θmax = 25.2°, θmin = 3.2°
ω and φ scansh = −17→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)k = −13→13
Tmin = 0.900, Tmax = 0.952l = −7→9
8991 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0422P)2 + 0.369P] where P = (Fo2 + 2Fc2)/3
2253 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.32 (release 27-01-2009 CrysAlis171 .NET) (compiled Jan 27 2009,14:17:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
S11.18567 (3)0.37673 (4)0.30521 (6)0.0398 (1)
O111.21041 (8)0.26127 (11)0.26279 (18)0.0556 (5)
O121.19451 (9)0.47053 (13)0.19034 (18)0.0621 (5)
N11.25128 (9)0.40557 (11)0.49616 (19)0.0418 (4)
N40.78277 (9)0.36050 (11)0.36083 (18)0.0389 (4)
C11.06568 (11)0.37128 (13)0.3201 (2)0.0345 (5)
C21.00490 (12)0.46245 (14)0.2581 (2)0.0420 (5)
C30.91150 (11)0.45702 (14)0.2709 (2)0.0431 (5)
C40.87847 (11)0.36039 (13)0.3457 (2)0.0350 (5)
C50.94078 (11)0.26993 (14)0.4104 (2)0.0383 (5)
C61.03363 (11)0.27468 (13)0.3960 (2)0.0380 (5)
C410.73681 (11)0.26550 (14)0.3389 (2)0.0409 (5)
C420.63915 (11)0.25305 (14)0.3574 (2)0.0405 (5)
C430.58382 (13)0.34722 (17)0.3798 (3)0.0584 (7)
C440.49211 (14)0.3309 (2)0.3954 (3)0.0685 (8)
C450.45425 (13)0.2225 (2)0.3881 (3)0.0638 (8)
C460.50775 (16)0.1288 (2)0.3660 (4)0.0746 (9)
C470.60028 (14)0.14359 (17)0.3505 (3)0.0629 (7)
H21.027300.528700.207000.0500*
H30.869800.519600.228300.0520*
H50.919100.204600.464800.0460*
H61.075500.212100.437900.0450*
H111.235000.471500.532200.0480*
H121.243800.352100.570000.0480*
H410.767600.198600.308800.0490*
H430.609200.423600.384500.0700*
H440.454900.396200.411600.0820*
H450.390800.212200.398200.0760*
H460.481500.052900.361200.0900*
H470.637000.077700.335100.0750*
U11U22U33U12U13U23
S10.0320 (2)0.0436 (2)0.0465 (3)−0.0013 (2)0.0148 (2)−0.0021 (2)
O110.0422 (7)0.0583 (8)0.0686 (9)0.0029 (6)0.0177 (6)−0.0237 (7)
O120.0473 (7)0.0774 (9)0.0668 (9)−0.0024 (6)0.0241 (6)0.0241 (7)
N10.0351 (7)0.0369 (7)0.0540 (9)−0.0028 (6)0.0118 (6)−0.0050 (6)
N40.0323 (7)0.0386 (7)0.0470 (8)0.0007 (6)0.0119 (6)−0.0024 (6)
C10.0308 (8)0.0361 (8)0.0373 (8)−0.0016 (6)0.0095 (6)−0.0039 (7)
C20.0416 (9)0.0326 (8)0.0550 (10)−0.0002 (7)0.0176 (8)0.0056 (7)
C30.0383 (9)0.0348 (8)0.0579 (11)0.0064 (7)0.0143 (8)0.0051 (8)
C40.0320 (8)0.0354 (8)0.0385 (8)−0.0003 (6)0.0102 (6)−0.0055 (7)
C50.0367 (8)0.0343 (8)0.0446 (9)−0.0019 (6)0.0109 (7)0.0041 (7)
C60.0336 (8)0.0347 (8)0.0443 (9)0.0027 (6)0.0064 (7)0.0031 (7)
C410.0359 (9)0.0387 (9)0.0488 (9)0.0015 (7)0.0112 (7)−0.0055 (7)
C420.0335 (8)0.0430 (9)0.0453 (9)−0.0030 (7)0.0097 (7)−0.0031 (7)
C430.0378 (10)0.0477 (10)0.0915 (15)−0.0012 (8)0.0188 (10)−0.0052 (10)
C440.0394 (11)0.0706 (14)0.0988 (17)0.0055 (10)0.0226 (11)−0.0102 (13)
C450.0366 (10)0.0868 (16)0.0701 (14)−0.0095 (10)0.0169 (9)−0.0023 (12)
C460.0548 (13)0.0639 (14)0.1079 (19)−0.0227 (11)0.0245 (13)−0.0024 (13)
C470.0462 (11)0.0489 (11)0.0965 (16)−0.0058 (9)0.0225 (11)−0.0086 (11)
S1—O111.4337 (13)C42—C431.383 (3)
S1—O121.4256 (15)C43—C441.378 (3)
S1—N11.6051 (15)C44—C451.358 (3)
S1—C11.7737 (17)C45—C461.362 (3)
N4—C41.421 (2)C46—C471.387 (3)
N4—C411.271 (2)C2—H20.9500
N1—H120.8700C3—H30.9500
N1—H110.8600C5—H50.9500
C1—C61.388 (2)C6—H60.9500
C1—C21.384 (2)C41—H410.9500
C2—C31.384 (2)C43—H430.9500
C3—C41.390 (2)C44—H440.9500
C4—C51.395 (2)C45—H450.9500
C5—C61.379 (2)C46—H460.9500
C41—C421.465 (2)C47—H470.9500
C42—C471.375 (3)
S1···H6i3.1100H2···C5iii2.9900
O11···C6i3.398 (2)H2···C6iii3.0200
O11···N1i2.9845 (19)H5···C412.7000
O11···H45ii2.6500H5···H412.2600
O11···H62.6900H5···C2v3.0200
O11···H6i2.8400H5···C3v3.0400
O11···H12i2.1300H6···O112.6900
O12···H22.5500H6···S1v3.1100
O12···H41iii2.6800H6···O11v2.8400
O12···H47iii2.7900H11···N4iv2.1400
N1···N4iv2.9955 (18)H11···C3iv3.0100
N1···O11v2.9845 (19)H11···C4iv2.8400
N4···N1iv2.9955 (18)H11···H43iv2.5100
N1···H43iv2.8200H12···O11v2.1300
N4···H432.6700H41···C52.5900
N4···H11iv2.1400H41···H52.2600
C6···O11v3.398 (2)H41···H472.4000
C44···C47v3.542 (3)H41···O12vi2.6800
C47···C44i3.542 (3)H43···N42.6700
C2···H5i3.0200H43···H46vii2.5400
C3···H11iv3.0100H43···N1iv2.8200
C3···H5i3.0400H43···H11iv2.5100
C4···H11iv2.8400H45···O11ix2.6500
C5···H2vi2.9900H46···C43x3.0300
C5···H412.5900H46···H43x2.5400
C6···H2vi3.0200H46···C46viii2.9600
C41···H52.7000H46···H46viii2.4300
C43···H46vii3.0300H47···H412.4000
C46···H46viii2.9600H47···O12vi2.7900
H2···O122.5500
O11—S1—O12119.52 (8)C43—C44—C45120.8 (2)
O11—S1—N1106.13 (8)C44—C45—C46119.6 (2)
O11—S1—C1106.51 (7)C45—C46—C47120.4 (2)
O12—S1—N1107.74 (8)C42—C47—C46120.39 (19)
O12—S1—C1107.41 (8)C1—C2—H2120.00
N1—S1—C1109.25 (7)C3—C2—H2120.00
C4—N4—C41118.77 (13)C2—C3—H3120.00
H11—N1—H12109.00C4—C3—H3120.00
S1—N1—H11110.00C4—C5—H5120.00
S1—N1—H12109.00C6—C5—H5120.00
S1—C1—C2120.51 (12)C1—C6—H6120.00
S1—C1—C6119.12 (12)C5—C6—H6120.00
C2—C1—C6120.36 (15)N4—C41—H41118.00
C1—C2—C3119.85 (15)C42—C41—H41118.00
C2—C3—C4120.29 (15)C42—C43—H43120.00
C3—C4—C5119.33 (15)C44—C43—H43120.00
N4—C4—C5122.43 (14)C43—C44—H44120.00
N4—C4—C3118.17 (14)C45—C44—H44120.00
C4—C5—C6120.41 (15)C44—C45—H45120.00
C1—C6—C5119.73 (15)C46—C45—H45120.00
N4—C41—C42124.13 (15)C45—C46—H46120.00
C41—C42—C43122.64 (15)C47—C46—H46120.00
C41—C42—C47118.91 (16)C42—C47—H47120.00
C43—C42—C47118.45 (17)C46—C47—H47120.00
C42—C43—C44120.38 (18)
O11—S1—C1—C2−141.95 (13)C2—C3—C4—C51.1 (2)
O11—S1—C1—C638.53 (15)N4—C4—C5—C6−178.65 (14)
O12—S1—C1—C2−12.78 (15)C3—C4—C5—C6−1.8 (2)
O12—S1—C1—C6167.69 (13)C4—C5—C6—C11.4 (2)
N1—S1—C1—C2103.82 (13)N4—C41—C42—C438.1 (3)
N1—S1—C1—C6−75.71 (14)N4—C41—C42—C47−172.62 (17)
C41—N4—C4—C3143.94 (15)C41—C42—C43—C44179.57 (18)
C41—N4—C4—C5−39.2 (2)C47—C42—C43—C440.3 (3)
C4—N4—C41—C42177.62 (14)C41—C42—C47—C46−179.4 (2)
S1—C1—C2—C3−179.89 (12)C43—C42—C47—C46−0.1 (3)
C6—C1—C2—C3−0.4 (2)C42—C43—C44—C45−0.4 (3)
S1—C1—C6—C5179.21 (12)C43—C44—C45—C460.3 (4)
C2—C1—C6—C5−0.3 (2)C44—C45—C46—C47−0.2 (4)
C1—C2—C3—C40.0 (2)C45—C46—C47—C420.1 (4)
C2—C3—C4—N4178.08 (14)
D—H···AD—HH···AD···AD—H···A
N1—H11···N4iv0.862.142.9955 (18)171
N1—H12···O11v0.872.132.9845 (19)171
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H11⋯N4i0.862.142.9955 (18)171
N1—H12⋯O11ii0.872.132.9845 (19)171

Symmetry codes: (i) ; (ii) .

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