organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

4-Chloro-N-(3,4-di­chloro­phen­yl)-2-methyl­benzene­sulfonamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 5 October 2011; accepted 10 October 2011; online 12 October 2011)

In the title compound, C13H10Cl3NO2S, the N—C bond in the C—SO2—NH—C segment forms trans and gauche torsion angles with respect to the S=O bonds. Further, the N—H bond in the C—SO2—NH—C segment is anti to the meta-Cl atom in the anilino benzene ring and nearly syn with respect to the ortho-methyl group in the sulfonyl benzene ring. The C—SO2—NH—C torsion angle is −49.4 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 54.6 (1)°. In the crystal, mol­ecules are linked into chains along the c-axis direction by inter­molecular N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006[Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 61, 600-606.]). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001[Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.]). For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2003[Gowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 58, 801-806.]), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337.]), on N-(ar­yl)-aryl­sulfonamides, see: Gelbrich et al. (2007[Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.]); Perlovich et al. (2006[Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780-o782.]); Rodrigues et al. (2011[Rodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2930.]); Shetty & Gowda (2005[Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113-120.]) and on N-(chloro)-aryl­sulfonamides, see: Gowda & Kumar (2003[Gowda, B. T. & Kumar, B. H. A. (2003). Oxid. Commun. A, 26, 403-425.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10Cl3NO2S

  • Mr = 350.63

  • Monoclinic, P 21 /c

  • a = 14.563 (2) Å

  • b = 10.033 (2) Å

  • c = 10.162 (2) Å

  • β = 92.60 (2)°

  • V = 1483.2 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.76 mm−1

  • T = 293 K

  • 0.44 × 0.44 × 0.38 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.732, Tmax = 0.762

  • 5266 measured reflections

  • 3005 independent reflections

  • 2373 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.126

  • S = 1.05

  • 3005 reflections

  • 185 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.42 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.85 (2) 2.11 (2) 2.868 (3) 149 (3)
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The sulfonamide moiety is the constituent of many biologically significant compounds. The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2003), N-(aryl)-methanesulfonamides (Gowda et al., 2007), N-(aryl)-arylsulfonamides (Rodrigues et al., 2011; Shetty & Gowda, 2005) and N-(chloro)-arylsulfonamides (Gowda & Kumar, 2003), in the present work, the crystal structure of 4-chloro-2-methyl-N-(3,4-dichlorophenyl)benzenesulfonamide (I) has been determined (Fig. 1).

In (I), the conformation of the N—C bond in the C—SO2—NH—C segment has trans and gauche torsions with respect to the SO bonds. Further, the N—H bond in the C—SO2—NH—C segment is anti with respect to the meta-Cl atom in the anilino benzene ring and nearly syn with respect to the ortho-methyl group in the sulfonyl benzene ring. The molecule is bent at the S atom with the C—SO2—NH—C torsion angle of -49.42 (23)°, compared to the value of -49.72 (18)° in 4-Chloro-2-methyl-N-(3,4-dimethylphenyl)- benzenesulfonamide (II) (Rodrigues et al., 2011).

The sulfonyl and the aniline benzene rings are tilted relative to each other by 54.6 (1)°, compared to the values of 71.6 (1)° in (II).

The other bond parameters in (I) are similar to those observed in (II) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal, the intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into infinite chains. Part of the crystal structure is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2003), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007), on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006); Rodrigues et al. (2011); Shetty & Gowda (2005) and on N-(chloro)-arylsulfonamides, see: Gowda & Kumar (2003).

Experimental top

The solution of m-chlorotoluene (10 ml) in chloroform (40 ml) was treated drop wise with chlorosulfonic acid (25 ml) at 273 K. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 2-methyl-4-chlorobenzenesulfonylchloride was treated with a stoichiometric amount of 3,4-dichloroaniline and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice-cold water (100 ml). The resultant solid, 4-chloro-2-methyl-N- (3,4-dichlorophenyl)benzenesulfonamide, was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol (Savitha & Gowda, 2006). Colourless prisms were grown from its ethanol solution by slow evaporation at room temperature.

Refinement top

The NH H atom was located in a difference map and later restrained to N—H = 0.86±0.02 Å. The other H atoms were positioned with idealized geometries using a riding model with the aromatic-C—H = 0.93 Å and methyl-C—H = 0.96 Å. The Uiso(H) values were set at 1.2Ueq(C-aromatic, N) and 1.5Ueq(C-methyl).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
4-Chloro-N-(3,4-dichlorophenyl)-2-methylbenzenesulfonamide top
Crystal data top
C13H10Cl3NO2SF(000) = 712
Mr = 350.63Dx = 1.570 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 926 reflections
a = 14.563 (2) Åθ = 2.9–27.8°
b = 10.033 (2) ŵ = 0.76 mm1
c = 10.162 (2) ÅT = 293 K
β = 92.60 (2)°Prism, colourless
V = 1483.2 (5) Å30.44 × 0.44 × 0.38 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
3005 independent reflections
Radiation source: fine-focus sealed tube2373 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Rotation method data acquisition using ω scansθmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1817
Tmin = 0.732, Tmax = 0.762k = 712
5266 measured reflectionsl = 1112
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0556P)2 + 1.2273P]
where P = (Fo2 + 2Fc2)/3
3005 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.41 e Å3
1 restraintΔρmin = 0.42 e Å3
Crystal data top
C13H10Cl3NO2SV = 1483.2 (5) Å3
Mr = 350.63Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.563 (2) ŵ = 0.76 mm1
b = 10.033 (2) ÅT = 293 K
c = 10.162 (2) Å0.44 × 0.44 × 0.38 mm
β = 92.60 (2)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
3005 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
2373 reflections with I > 2σ(I)
Tmin = 0.732, Tmax = 0.762Rint = 0.021
5266 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.41 e Å3
3005 reflectionsΔρmin = 0.42 e Å3
185 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.35205 (17)0.5208 (3)0.4395 (2)0.0366 (5)
C20.39656 (16)0.5884 (3)0.3403 (2)0.0376 (5)
C30.38485 (18)0.7259 (3)0.3330 (3)0.0426 (6)
H30.41400.77400.26880.051*
C40.33077 (18)0.7916 (3)0.4196 (3)0.0445 (6)
C50.2867 (2)0.7245 (3)0.5166 (3)0.0517 (7)
H50.25050.77030.57460.062*
C60.2973 (2)0.5885 (3)0.5262 (3)0.0487 (7)
H60.26770.54160.59090.058*
C70.19793 (17)0.3372 (3)0.3148 (2)0.0384 (6)
C80.1756 (2)0.4145 (3)0.2057 (3)0.0519 (7)
H80.22080.43760.14800.062*
C90.0865 (2)0.4577 (4)0.1820 (3)0.0656 (9)
H90.07150.50900.10790.079*
C100.0196 (2)0.4247 (4)0.2682 (3)0.0597 (8)
C110.0421 (2)0.3503 (3)0.3786 (3)0.0517 (7)
C120.13136 (19)0.3057 (3)0.4024 (3)0.0454 (6)
H120.14640.25490.47680.054*
C130.4565 (2)0.5208 (3)0.2399 (3)0.0542 (8)
H13A0.42250.45020.19660.065*
H13B0.51060.48470.28430.065*
H13C0.47420.58500.17570.065*
Cl10.31845 (6)0.96380 (8)0.40549 (10)0.0668 (3)
Cl20.09220 (7)0.47671 (15)0.23365 (13)0.1025 (4)
Cl30.04016 (6)0.30826 (11)0.48889 (11)0.0810 (3)
N10.28934 (15)0.2871 (2)0.3357 (2)0.0413 (5)
H1N0.3167 (19)0.274 (3)0.265 (2)0.050*
O10.31664 (17)0.3122 (2)0.57571 (19)0.0578 (6)
O20.44650 (14)0.2959 (2)0.4296 (2)0.0573 (5)
S10.35718 (5)0.34532 (7)0.45424 (6)0.04128 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0362 (12)0.0393 (13)0.0344 (12)0.0026 (10)0.0007 (10)0.0030 (10)
C20.0325 (11)0.0432 (14)0.0376 (12)0.0018 (11)0.0069 (10)0.0038 (11)
C30.0389 (13)0.0426 (14)0.0469 (14)0.0051 (11)0.0084 (11)0.0019 (12)
C40.0405 (13)0.0389 (14)0.0540 (16)0.0015 (11)0.0014 (12)0.0059 (12)
C50.0524 (16)0.0505 (17)0.0537 (16)0.0012 (13)0.0183 (13)0.0147 (14)
C60.0545 (16)0.0531 (17)0.0398 (14)0.0078 (14)0.0172 (12)0.0049 (13)
C70.0432 (13)0.0350 (13)0.0369 (13)0.0034 (11)0.0004 (10)0.0055 (10)
C80.0549 (16)0.0552 (18)0.0458 (15)0.0018 (14)0.0053 (13)0.0072 (14)
C90.069 (2)0.074 (2)0.0538 (18)0.0123 (18)0.0016 (16)0.0139 (17)
C100.0492 (16)0.066 (2)0.0632 (19)0.0130 (15)0.0027 (15)0.0027 (16)
C110.0478 (15)0.0518 (17)0.0559 (17)0.0030 (13)0.0079 (13)0.0032 (14)
C120.0496 (15)0.0443 (15)0.0423 (14)0.0013 (12)0.0025 (12)0.0010 (12)
C130.0536 (16)0.0486 (16)0.0631 (18)0.0065 (14)0.0322 (15)0.0066 (14)
Cl10.0696 (5)0.0436 (4)0.0880 (6)0.0018 (4)0.0133 (4)0.0057 (4)
Cl20.0603 (5)0.1361 (11)0.1105 (9)0.0337 (6)0.0036 (6)0.0203 (8)
Cl30.0575 (5)0.0977 (7)0.0900 (7)0.0007 (5)0.0267 (5)0.0084 (6)
N10.0458 (12)0.0412 (12)0.0369 (11)0.0017 (10)0.0039 (9)0.0053 (10)
O10.0820 (15)0.0555 (12)0.0357 (10)0.0111 (11)0.0012 (10)0.0099 (9)
O20.0465 (11)0.0550 (12)0.0693 (14)0.0099 (10)0.0077 (10)0.0041 (11)
S10.0465 (4)0.0410 (4)0.0360 (3)0.0022 (3)0.0017 (3)0.0034 (3)
Geometric parameters (Å, º) top
C1—C61.392 (4)C8—H80.9300
C1—C21.399 (4)C9—C101.380 (5)
C1—S11.768 (3)C9—H90.9300
C2—C31.392 (4)C10—C111.375 (4)
C2—C131.531 (4)C10—Cl21.730 (3)
C3—C41.375 (4)C11—C121.386 (4)
C3—H30.9300C11—Cl31.729 (3)
C4—C51.376 (4)C12—H120.9300
C4—Cl11.743 (3)C13—H13A0.9600
C5—C61.377 (4)C13—H13B0.9600
C5—H50.9300C13—H13C0.9600
C6—H60.9300N1—S11.631 (2)
C7—C81.380 (4)N1—H1N0.847 (17)
C7—C121.382 (4)O1—S11.431 (2)
C7—N11.430 (3)O2—S11.425 (2)
C8—C91.378 (4)
C6—C1—C2121.2 (3)C10—C9—H9120.0
C6—C1—S1117.1 (2)C11—C10—C9119.9 (3)
C2—C1—S1121.61 (19)C11—C10—Cl2121.1 (3)
C3—C2—C1117.3 (2)C9—C10—Cl2119.0 (3)
C3—C2—C13118.4 (2)C10—C11—C12120.3 (3)
C1—C2—C13124.3 (2)C10—C11—Cl3121.0 (2)
C4—C3—C2120.9 (3)C12—C11—Cl3118.7 (2)
C4—C3—H3119.5C7—C12—C11119.6 (3)
C2—C3—H3119.5C7—C12—H12120.2
C3—C4—C5121.5 (3)C11—C12—H12120.2
C3—C4—Cl1118.9 (2)C2—C13—H13A109.5
C5—C4—Cl1119.6 (2)C2—C13—H13B109.5
C4—C5—C6118.8 (3)H13A—C13—H13B109.5
C4—C5—H5120.6C2—C13—H13C109.5
C6—C5—H5120.6H13A—C13—H13C109.5
C5—C6—C1120.3 (3)H13B—C13—H13C109.5
C5—C6—H6119.9C7—N1—S1120.79 (18)
C1—C6—H6119.9C7—N1—H1N114 (2)
C8—C7—C12120.0 (3)S1—N1—H1N113 (2)
C8—C7—N1120.0 (2)O2—S1—O1119.09 (14)
C12—C7—N1120.0 (2)O2—S1—N1105.82 (13)
C9—C8—C7120.2 (3)O1—S1—N1107.11 (13)
C9—C8—H8119.9O2—S1—C1111.54 (13)
C7—C8—H8119.9O1—S1—C1106.65 (13)
C8—C9—C10120.0 (3)N1—S1—C1105.81 (12)
C8—C9—H9120.0
C6—C1—C2—C30.9 (4)Cl2—C10—C11—C12177.8 (2)
S1—C1—C2—C3177.02 (19)C9—C10—C11—Cl3179.6 (3)
C6—C1—C2—C13178.9 (3)Cl2—C10—C11—Cl31.2 (4)
S1—C1—C2—C132.8 (4)C8—C7—C12—C111.1 (4)
C1—C2—C3—C40.7 (4)N1—C7—C12—C11177.4 (2)
C13—C2—C3—C4179.1 (3)C10—C11—C12—C70.4 (5)
C2—C3—C4—C50.3 (4)Cl3—C11—C12—C7179.4 (2)
C2—C3—C4—Cl1179.8 (2)C8—C7—N1—S1109.5 (3)
C3—C4—C5—C60.2 (4)C12—C7—N1—S172.0 (3)
Cl1—C4—C5—C6180.0 (2)C7—N1—S1—O2167.9 (2)
C4—C5—C6—C10.4 (4)C7—N1—S1—O164.1 (2)
C2—C1—C6—C50.8 (4)C7—N1—S1—C149.4 (2)
S1—C1—C6—C5177.1 (2)C6—C1—S1—O2143.8 (2)
C12—C7—C8—C91.7 (5)C2—C1—S1—O240.0 (2)
N1—C7—C8—C9176.9 (3)C6—C1—S1—O112.2 (2)
C7—C8—C9—C100.7 (5)C2—C1—S1—O1171.5 (2)
C8—C9—C10—C110.8 (5)C6—C1—S1—N1101.6 (2)
C8—C9—C10—Cl2178.4 (3)C2—C1—S1—N174.6 (2)
C9—C10—C11—C121.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.85 (2)2.11 (2)2.868 (3)149 (3)
Symmetry code: (i) x, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC13H10Cl3NO2S
Mr350.63
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.563 (2), 10.033 (2), 10.162 (2)
β (°) 92.60 (2)
V3)1483.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.76
Crystal size (mm)0.44 × 0.44 × 0.38
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.732, 0.762
No. of measured, independent and
observed [I > 2σ(I)] reflections
5266, 3005, 2373
Rint0.021
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.126, 1.05
No. of reflections3005
No. of parameters185
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.41, 0.42

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.847 (17)2.11 (2)2.868 (3)149 (3)
Symmetry code: (i) x, y+1/2, z1/2.
 

Acknowledgements

VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS fellowship.

References

First citationAdsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058–2077.  Web of Science CrossRef PubMed CAS Google Scholar
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