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ISSN: 2056-9890

2-(3,5-Di­methyl-1,1-dioxo-2H-1λ6,2,6-thia­diazin-4-yl)benzoic acid

aChemistry Department, JJT University, Rajasthan, India, bSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa, and cSchool of Pharmacology, University of KwaZulu Natal, Westville Campus, Private Bag X54001, South Africa
*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 23 July 2012; accepted 27 August 2012; online 5 September 2012)

In the title mol­ecule, C12H12N2O4S, the S atom of the thia­diazine ring deviates by 0.5104 (4) Å from the mean plane of the other five atoms [largest deviation = 0.0623 (15) Å] giving a slightly distorted sofa conformation. The carb­oxy H atom was refined as disordered over two sets of sites with refined occupancies of 0.58 (2) and 0.48 (2). This corresponds to rotational disorder of the C=O and O—H groups about the attached C—C bond. In the crystal, O—H⋯O and N—H⋯O hydrogen bonds connect the mol­ecules into chains along [110].

Related literature

The title compound is a phenyl acid thia­diazine derivative. For synthetic background and applications of 1,2,6-thia­diazine-1,1-dioxide derivatives, see: Wright (1964[Wright, J. B. (1964). J. Org. Chem. 29, 1905-1909.]); Breining et al. (1995[Breining, T., Cimpoia, A. R., Mansour, T. S., Cammack, N., Hopewell, P. & Ashman, C. (1995). Heterocycles, 41, 87-94.]). For a related structure, see: Bhatt et al. (2012[Bhatt, N., Bhatt, P., Vyas, K. B., Nimavat, K., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2012). Acta Cryst. E68, o2160.])

[Scheme 1]

Experimental

Crystal data
  • C12H12N2O4S

  • Mr = 280.30

  • Monoclinic, P 21 /n

  • a = 10.5048 (14) Å

  • b = 10.4254 (13) Å

  • c = 11.1294 (14) Å

  • β = 92.772 (4)°

  • V = 1217.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 173 K

  • 0.24 × 0.19 × 0.18 mm

Data collection
  • Bruker Kappa DUO APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.936, Tmax = 0.952

  • 5724 measured reflections

  • 3030 independent reflections

  • 2573 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.103

  • S = 1.05

  • 3030 reflections

  • 187 parameters

  • 3 restraints

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

  • Δρmax = 0.37 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—H1⋯O1i 0.97 (1) 2.09 (2) 2.9699 (18) 151 (2)
O4—H4⋯O3ii 0.97 (3) 1.64 (3) 2.6103 (19) 177 (3)
O3—H3⋯O4ii 0.97 (3) 1.67 (3) 2.6103 (19) 161 (5)
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The synthesis of 1,2,6-thiadiazine-1,1-dioxides derivatives was first reported using sulfamide with alpha and beta diketones (Wright, 1964). Anti-HIV-1 activity for this family of structures was also reported (Breining et al., 1995). For this reason we are interested in this class of compounds as potential agents in other diseases. The crystal structure of the title compound is described herein.

The molecular structure of the title compound is shown in Fig. 1. It is the second 3,5-dimethyl based structure reported with an aromatic ring at position 4 of the thiadiazine ring. Previously we have reported the phenyl ethyl and methyl ester (Bhatt et al., 2012). It is the first containing an acid functional group in the broader family of 1,2,6-thiadiazine-1,1-dioxides. The S atom of the thiadiazine ring deviates by 0.5104 (4) Å from the plane of the other five atoms [largest deviation 0.0623 (15) Å] giving a slightly distorted sofa conformation. The carboxylic acid H atom was refined as disordered over two sets of sites with refined occupancies 0.58 (2) and 0.48 (2). This corresponds to roational disorder of the CO and O—H groups about the attached C—C bond. In the crystal, O—H···O and N—H···O hydrogen bonds connect molecules into chains along [110] (Fig. 2).

Related literature top

The title compound is a phenyl acid thiadiazine derivative. For synthetic background and applications of 1,2,6-thiadiazine-1,1-dioxide derivatives, see: Wright (1964); Breining et al. (1995). For a related structure, see: Bhatt et al. (2012)

Experimental top

2-(2, 4-dioxopentan-3-yl) benzoic acid (0.072 mol) and sulfamide (0.072 mol) were dissolved in methanol (70 ml). Anhydrous hydrogen chloride gas was bubbled into the mixture until the temperature increased to 323 K. The contents of the reaction were then refluxed for 3hrs. The reaction mixture was cooled, filtered and the filtrate was concentrated under reduced pressure. The residual solid was treated with NaOH (0.138 mol) in water (200 ml), the contents were heated at 343 K for 2.5 hrs. The reaction progress was monitored by TLC ethyl acetate/hexane (80:20 Rf = 1/2). The reaction mixture was cooled and acidified using concentrated HCl to get the crude acid as an oil. To this oily residue was added a solution of methanol/ethyl acetate (10 ml) (10/90) which yielded a white colourless solid (79%). M.p.= 523 K. Crystals suitable for X-ray analysis were grown in dioxane/water at room temprature.

Refinement top

All hydrogen atoms, except H1, H3 and H4, were placed in idealized positions and refined with geometric constraints [C—H = 0.95 - 0.98 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl). The hydrogen atom H1 was located in a difference Fourier map and refined with O—H distance restraint to the value of 0.97 (1) Å. The carboxy hydroxyl hydrogen is distributed over two sites: H3 and H4, were both located in a difference Fourier map and refined with a O—H distance restraint to the value of 0.97 (1) Å. The site occupancy factors refined to 0.48 (8) for H3 and 0.52 (8) for H4.

Structure description top

The synthesis of 1,2,6-thiadiazine-1,1-dioxides derivatives was first reported using sulfamide with alpha and beta diketones (Wright, 1964). Anti-HIV-1 activity for this family of structures was also reported (Breining et al., 1995). For this reason we are interested in this class of compounds as potential agents in other diseases. The crystal structure of the title compound is described herein.

The molecular structure of the title compound is shown in Fig. 1. It is the second 3,5-dimethyl based structure reported with an aromatic ring at position 4 of the thiadiazine ring. Previously we have reported the phenyl ethyl and methyl ester (Bhatt et al., 2012). It is the first containing an acid functional group in the broader family of 1,2,6-thiadiazine-1,1-dioxides. The S atom of the thiadiazine ring deviates by 0.5104 (4) Å from the plane of the other five atoms [largest deviation 0.0623 (15) Å] giving a slightly distorted sofa conformation. The carboxylic acid H atom was refined as disordered over two sets of sites with refined occupancies 0.58 (2) and 0.48 (2). This corresponds to roational disorder of the CO and O—H groups about the attached C—C bond. In the crystal, O—H···O and N—H···O hydrogen bonds connect molecules into chains along [110] (Fig. 2).

The title compound is a phenyl acid thiadiazine derivative. For synthetic background and applications of 1,2,6-thiadiazine-1,1-dioxide derivatives, see: Wright (1964); Breining et al. (1995). For a related structure, see: Bhatt et al. (2012)

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 40% probability. Atoms H3 and H4 are disorder components.
[Figure 2] Fig. 2. The hydrogen bonding interactions of the title compound along [110]. All H atoms except those involved in hydrogen bonding have been omitted for clarity.
2-(3,5-Dimethyl-1,1-dioxo-2H-1λ6,2,6-thiadiazin-4-yl)benzoic acid top
Crystal data top
C12H12N2O4SF(000) = 584
Mr = 280.30Dx = 1.529 Mg m3
Dm = 0 Mg m3
Dm measured by not measured
Monoclinic, P21/nMelting point: 523 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.5048 (14) ÅCell parameters from 5724 reflections
b = 10.4254 (13) Åθ = 2.6–28.4°
c = 11.1294 (14) ŵ = 0.28 mm1
β = 92.772 (4)°T = 173 K
V = 1217.4 (3) Å30, colourless
Z = 40.24 × 0.19 × 0.18 mm
Data collection top
Bruker Kappa DUO APEXII
diffractometer
3030 independent reflections
Radiation source: fine-focus sealed tube2573 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
0.5° φ scans and ω scansθmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 1214
Tmin = 0.936, Tmax = 0.952k = 1312
5724 measured reflectionsl = 1114
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0518P)2 + 0.4988P]
where P = (Fo2 + 2Fc2)/3
3030 reflections(Δ/σ)max = 0.001
187 parametersΔρmax = 0.37 e Å3
3 restraintsΔρmin = 0.42 e Å3
Crystal data top
C12H12N2O4SV = 1217.4 (3) Å3
Mr = 280.30Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.5048 (14) ŵ = 0.28 mm1
b = 10.4254 (13) ÅT = 173 K
c = 11.1294 (14) Å0.24 × 0.19 × 0.18 mm
β = 92.772 (4)°
Data collection top
Bruker Kappa DUO APEXII
diffractometer
3030 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
2573 reflections with I > 2σ(I)
Tmin = 0.936, Tmax = 0.952Rint = 0.020
5724 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0383 restraints
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.37 e Å3
3030 reflectionsΔρmin = 0.42 e Å3
187 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*/UeqOcc. (<1)
S10.98957 (3)0.13712 (4)0.12970 (3)0.02250 (12)
O11.01274 (12)0.00736 (13)0.16838 (11)0.0344 (3)
O21.09339 (11)0.20118 (15)0.07866 (12)0.0395 (3)
O30.39308 (11)0.41036 (12)0.06653 (11)0.0311 (3)
O40.60472 (11)0.39428 (13)0.08005 (13)0.0353 (3)
N10.87045 (12)0.13786 (13)0.02772 (11)0.0231 (3)
N20.93605 (12)0.21970 (13)0.23740 (12)0.0241 (3)
C10.65248 (16)0.09799 (18)0.03955 (14)0.0285 (3)
H1A0.56770.08830.00760.043*
H1B0.67840.01680.07540.043*
H1C0.65000.16530.10100.043*
C20.74610 (14)0.13394 (14)0.06012 (13)0.0201 (3)
C30.71616 (13)0.16832 (14)0.17403 (13)0.0192 (3)
C40.81280 (14)0.22158 (14)0.25478 (13)0.0208 (3)
C50.77422 (16)0.29238 (17)0.36412 (15)0.0293 (4)
H5A0.84830.33740.40070.044*
H5B0.74160.23140.42220.044*
H5C0.70760.35470.34120.044*
C60.58294 (14)0.15746 (14)0.21603 (13)0.0204 (3)
C70.48160 (14)0.24135 (14)0.18462 (13)0.0206 (3)
C80.36101 (15)0.21905 (16)0.22911 (14)0.0252 (3)
H80.29250.27490.20670.030*
C90.34023 (16)0.11711 (17)0.30514 (15)0.0292 (4)
H90.25810.10350.33490.035*
C100.43933 (16)0.03505 (17)0.33774 (15)0.0296 (4)
H100.42570.03490.39030.036*
C110.55916 (16)0.05546 (15)0.29322 (14)0.0263 (3)
H110.62670.00150.31590.032*
C120.49362 (14)0.35576 (14)0.10521 (14)0.0217 (3)
H40.606 (4)0.469 (2)0.028 (3)0.030 (16)*0.52 (8)
H30.406 (6)0.491 (3)0.025 (5)0.06 (2)*0.48 (8)
H10.892 (2)0.113 (2)0.0528 (8)0.047 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01708 (18)0.0281 (2)0.02257 (19)0.00231 (14)0.00382 (13)0.00124 (14)
O10.0401 (7)0.0339 (7)0.0292 (6)0.0161 (6)0.0017 (5)0.0019 (5)
O20.0237 (6)0.0582 (9)0.0374 (7)0.0106 (6)0.0105 (5)0.0040 (6)
O30.0259 (6)0.0294 (6)0.0376 (7)0.0023 (5)0.0030 (5)0.0086 (5)
O40.0255 (6)0.0308 (6)0.0503 (8)0.0038 (5)0.0102 (5)0.0165 (6)
N10.0207 (6)0.0306 (7)0.0182 (6)0.0028 (5)0.0029 (5)0.0019 (5)
N20.0201 (6)0.0278 (7)0.0246 (6)0.0012 (5)0.0017 (5)0.0048 (5)
C10.0275 (8)0.0347 (9)0.0231 (7)0.0019 (7)0.0012 (6)0.0041 (7)
C20.0201 (7)0.0183 (7)0.0219 (7)0.0013 (5)0.0018 (5)0.0012 (6)
C30.0182 (6)0.0178 (6)0.0218 (7)0.0022 (5)0.0030 (5)0.0010 (5)
C40.0228 (7)0.0193 (7)0.0204 (6)0.0026 (6)0.0026 (5)0.0000 (5)
C50.0275 (8)0.0350 (9)0.0256 (7)0.0028 (7)0.0024 (6)0.0096 (7)
C60.0196 (7)0.0211 (7)0.0207 (6)0.0005 (6)0.0035 (5)0.0006 (5)
C70.0191 (7)0.0206 (7)0.0222 (7)0.0010 (6)0.0027 (5)0.0011 (6)
C80.0191 (7)0.0281 (8)0.0285 (7)0.0005 (6)0.0031 (6)0.0019 (6)
C90.0242 (8)0.0326 (9)0.0313 (8)0.0066 (7)0.0081 (6)0.0011 (7)
C100.0338 (9)0.0278 (8)0.0279 (8)0.0048 (7)0.0071 (6)0.0039 (7)
C110.0277 (8)0.0233 (8)0.0281 (7)0.0024 (6)0.0038 (6)0.0036 (6)
C120.0212 (7)0.0202 (7)0.0236 (7)0.0012 (6)0.0016 (5)0.0014 (6)
Geometric parameters (Å, º) top
S1—O21.4206 (12)C3—C61.5011 (19)
S1—O11.4368 (13)C4—C51.496 (2)
S1—N21.5998 (13)C5—H5A0.9800
S1—N11.6483 (13)C5—H5B0.9800
O3—C121.2573 (19)C5—H5C0.9800
O3—H30.9699 (10)C6—C111.397 (2)
O4—C121.2781 (18)C6—C71.409 (2)
O4—H40.9699 (10)C7—C81.402 (2)
N1—C21.3724 (19)C7—C121.493 (2)
N1—H10.9698 (10)C8—C91.382 (2)
N2—C41.3185 (19)C8—H80.9500
C1—C21.494 (2)C9—C101.382 (2)
C1—H1A0.9800C9—H90.9500
C1—H1B0.9800C10—C111.391 (2)
C1—H1C0.9800C10—H100.9500
C2—C31.369 (2)C11—H110.9500
C3—C41.435 (2)
O2—S1—O1116.12 (8)C4—C5—H5A109.5
O2—S1—N2110.55 (8)C4—C5—H5B109.5
O1—S1—N2110.05 (7)H5A—C5—H5B109.5
O2—S1—N1107.12 (8)C4—C5—H5C109.5
O1—S1—N1108.82 (8)H5A—C5—H5C109.5
N2—S1—N1103.34 (7)H5B—C5—H5C109.5
C12—O3—H3115 (4)C11—C6—C7118.02 (13)
C12—O4—H4115 (2)C11—C6—C3116.49 (13)
C2—N1—S1121.29 (10)C7—C6—C3125.49 (13)
C2—N1—H1120.0 (14)C8—C7—C6119.63 (14)
S1—N1—H1115.7 (14)C8—C7—C12116.44 (13)
C4—N2—S1120.07 (11)C6—C7—C12123.94 (13)
C2—C1—H1A109.5C9—C8—C7121.06 (15)
C2—C1—H1B109.5C9—C8—H8119.5
H1A—C1—H1B109.5C7—C8—H8119.5
C2—C1—H1C109.5C10—C9—C8119.82 (15)
H1A—C1—H1C109.5C10—C9—H9120.1
H1B—C1—H1C109.5C8—C9—H9120.1
C3—C2—N1119.99 (14)C9—C10—C11119.65 (15)
C3—C2—C1125.51 (14)C9—C10—H10120.2
N1—C2—C1114.40 (13)C11—C10—H10120.2
C2—C3—C4119.62 (13)C10—C11—C6121.82 (15)
C2—C3—C6121.88 (13)C10—C11—H11119.1
C4—C3—C6118.44 (12)C6—C11—H11119.1
N2—C4—C3124.92 (13)O3—C12—O4122.93 (14)
N2—C4—C5115.67 (13)O3—C12—C7118.07 (13)
C3—C4—C5119.29 (13)O4—C12—C7119.00 (13)
O2—S1—N1—C2152.60 (12)C4—C3—C6—C1178.20 (18)
O1—S1—N1—C281.12 (13)C2—C3—C6—C775.8 (2)
N2—S1—N1—C235.82 (14)C4—C3—C6—C7101.44 (18)
O2—S1—N2—C4143.83 (13)C11—C6—C7—C81.2 (2)
O1—S1—N2—C486.58 (14)C3—C6—C7—C8179.14 (14)
N1—S1—N2—C429.49 (14)C11—C6—C7—C12178.69 (14)
S1—N1—C2—C320.0 (2)C3—C6—C7—C120.9 (2)
S1—N1—C2—C1163.46 (12)C6—C7—C8—C91.1 (2)
N1—C2—C3—C46.8 (2)C12—C7—C8—C9178.81 (15)
C1—C2—C3—C4169.34 (15)C7—C8—C9—C100.3 (3)
N1—C2—C3—C6175.96 (13)C8—C9—C10—C110.3 (3)
C1—C2—C3—C67.9 (2)C9—C10—C11—C60.2 (3)
S1—N2—C4—C39.0 (2)C7—C6—C11—C100.6 (2)
S1—N2—C4—C5174.88 (12)C3—C6—C11—C10179.72 (14)
C2—C3—C4—N213.2 (2)C8—C7—C12—O312.3 (2)
C6—C3—C4—N2169.49 (14)C6—C7—C12—O3167.81 (15)
C2—C3—C4—C5162.84 (15)C8—C7—C12—O4167.35 (15)
C6—C3—C4—C514.5 (2)C6—C7—C12—O412.6 (2)
C2—C3—C6—C11104.52 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.97 (1)2.09 (2)2.9699 (18)151 (2)
O4—H4···O3ii0.97 (3)1.64 (3)2.6103 (19)177 (3)
O3—H3···O4ii0.97 (3)1.67 (3)2.6103 (19)161 (5)
Symmetry codes: (i) x+2, y, z; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC12H12N2O4S
Mr280.30
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)10.5048 (14), 10.4254 (13), 11.1294 (14)
β (°) 92.772 (4)
V3)1217.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.24 × 0.19 × 0.18
Data collection
DiffractometerBruker Kappa DUO APEXII
Absorption correctionMulti-scan
(SADABS; Bruker, 2006)
Tmin, Tmax0.936, 0.952
No. of measured, independent and
observed [I > 2σ(I)] reflections
5724, 3030, 2573
Rint0.020
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.103, 1.05
No. of reflections3030
No. of parameters187
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.37, 0.42

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.970 (12)2.087 (17)2.9699 (18)150.5 (15)
O4—H4···O3ii0.97 (3)1.64 (3)2.6103 (19)177 (3)
O3—H3···O4ii0.97 (3)1.67 (3)2.6103 (19)161 (5)
Symmetry codes: (i) x+2, y, z; (ii) x+1, y+1, z.
 

Acknowledgements

The authors wish to thank Dr Hong Su from the University of Cape Town for assistance with the data collection and refinement.

References

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