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ISSN: 2056-9890

Ethyl 2-(5-fluoro-3-methyl­sulfinyl-1-benzo­furan-2-yl)acetate

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 1 July 2009; accepted 4 July 2009; online 11 July 2009)

In the title compound, C13H13FO4S, the O atom and the methyl group of the methyl­sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The crystal structure exhibits four inter­molecular non-classical C—H⋯O hydrogen bonds. In addition, the crystal structure contains aromatic ππ inter­actions between the furan and benzene rings of adjacent mol­ecules [centroid–centroid distance = 3.743 (2) Å], and two inter­molecular C—H⋯π inter­actions.

Related literature

For the crystal structures of similar ethyl 2-(5-halo-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2007a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007a). Acta Cryst. E63, o3832.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007b). Acta Cryst. E63, o3850.],c[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007c). Acta Cryst. E63, o4081.]). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999[Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283-289.]); Twyman & Allsop (1999[Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383-9384.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13FO4S

  • Mr = 284.29

  • Triclinic, [P \overline 1]

  • a = 7.8821 (5) Å

  • b = 9.0922 (5) Å

  • c = 10.4354 (6) Å

  • α = 73.682 (1)°

  • β = 79.155 (1)°

  • γ = 66.622 (1)°

  • V = 656.31 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.27 mm−1

  • T = 273 K

  • 0.40 × 0.40 × 0.10 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: none

  • 5673 measured reflections

  • 2805 independent reflections

  • 2512 reflections with I > 2σ(I)

  • Rint = 0.063

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.101

  • S = 1.04

  • 2805 reflections

  • 173 parameters

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯O4i 0.93 2.42 3.3374 (19) 168
C5—H5⋯O3ii 0.93 2.67 3.482 (2) 147
C9—H9A⋯O4iii 0.97 2.21 3.177 (2) 172
C9—H9B⋯O1iv 0.97 2.59 3.542 (2) 169
C11—H11ACg2v 0.97 2.92 3.773 (2) 148
C12—H12CCg1v 0.97 2.81 3.502 (2) 129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) -x+2, -y+1, -z+1; (iv) -x+2, -y+1, -z+2; (v) x, y+1, z.Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Molecules containing the benzofuran ring system have attracted considerable interest in view of their biological and pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999). This work is related to our communications on the synthesis and structures of ethyl 2-(5-halo-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, viz. ethyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2007a), ethyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl) acetate (Choi et al., 2007b), and ethyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2007c). Here we report the crystal structure of the title compound (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The crystal packing (Fig. 2) exhibits weak intermolecular C–H···O non-classical hydrogen bonds; the first between an H atom of the benzofuran ring and the SO unit, with a C3–H3···O4i, the second between an H atom of benzofuran ring and the CO unit, with a C5-H5···O3ii, the third between an H atom of the methylene group bonded to carboxylate C atom and the SO unit, with a C9–H9A···O4iii, the fourth between an H atom of the methylene group bonded to carboxylate C atom and the furan O atom, with a C9–H9B···O1iv, respectively (Table 1 and Fig. 2). Additionally, the crystal packing (Fig. 3) contains aromatic ππ interactions between the furan and the benzene rings of the neighbouring molecules, with a Cg1···Cg2vi distance of 3.743 (2) Å (Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2-C7 benzene ring, respectively). The molecular packing is further stabilized by two intermolecular C–H···π interactions; the first between the methylene H atom of ethoxy group and the benzene ring of a neighbouring molecule (C11–H11A···Cg2v), the second between the methyl H atom of ethoxy group and the furan ring of a neighbouring molecule (C12–H12C···Cg1v), respectively (Table 1 and Fig. 3).

Related literature top

For the crystal structures of similar ethyl 2-(5-halo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2007a,b,c). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999).

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2–C7 benzene ring, respectively.

Experimental top

77% 3-chloroperoxybenzoic acid (247 mg, 1.1 mmol) was added in small portions to a stirred solution of ethyl 2-(5-fluoro-3-methylsulfanyl-1-benzofuran-2-yl)acetate (268 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 4 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate,1:2 v/v) to afford the title compound as a colorless solid [yield 79%, m.p. 401-402 K; Rf = 0.43 (hexane-ethyl acetate, 1;2 v/v )]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetone at room temperature.

Refinement top

All H atoms were geometrically positioned and refined using a riding model, with C-H = 0.93 Å for the aryl, 0.97 Å for the methylene, and 0.96 Å for the methyl H atoms. Uiso(H) = 1.2Ueq(C) for the aryl and methylene H atoms, and 1.5Ueq(C) for methyl H atoms.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small cycles of arbitrary radius.
[Figure 2] Fig. 2. The C–H···O interactions (dotted lines) in the title compound. [Symmetry code: (i) - x + 1, - y + 1, - z + 1; (ii) - x + 1, - y + 1, - z + 2; (iii) - x + 2, - y + 1, - z + 1; (iv) - x + 2, - y + 1, - z + 2.]
[Figure 3] Fig. 3. The ππ and C–H···π interactions (dotted lines) in the title compound. Cg denotes the ring centroids. [Symmetry code: (v) x, 1 + y, z; (vi) 1 - x, 1 - y, 2 - z; (vii) 1 - x, 2 - y, 2 - z; (viii) x, - 1 + y, z.]
Ethyl 2-(5-fluoro-3-methylsulfinyl-1-benzofuran-2-yl)acetate top
Crystal data top
C13H13FO4SZ = 2
Mr = 284.29F(000) = 296
Triclinic, P1Dx = 1.439 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8821 (5) ÅCell parameters from 4105 reflections
b = 9.0922 (5) Åθ = 2.5–27.5°
c = 10.4354 (6) ŵ = 0.27 mm1
α = 73.682 (1)°T = 273 K
β = 79.155 (1)°Block, colourless
γ = 66.622 (1)°0.40 × 0.40 × 0.10 mm
V = 656.31 (7) Å3
Data collection top
Bruker SMART CCD
diffractometer
2512 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.063
Graphite monochromatorθmax = 27.0°, θmin = 2.0°
Detector resolution: 10.0 pixels mm-1h = 1010
ϕ and ω scansk = 1111
5673 measured reflectionsl = 1313
2805 independent reflections
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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.101H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0465P)2 + 0.2336P]
where P = (Fo2 + 2Fc2)/3
2805 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C13H13FO4Sγ = 66.622 (1)°
Mr = 284.29V = 656.31 (7) Å3
Triclinic, P1Z = 2
a = 7.8821 (5) ÅMo Kα radiation
b = 9.0922 (5) ŵ = 0.27 mm1
c = 10.4354 (6) ÅT = 273 K
α = 73.682 (1)°0.40 × 0.40 × 0.10 mm
β = 79.155 (1)°
Data collection top
Bruker SMART CCD
diffractometer
2512 reflections with I > 2σ(I)
5673 measured reflectionsRint = 0.063
2805 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.04Δρmax = 0.40 e Å3
2805 reflectionsΔρmin = 0.35 e Å3
173 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S0.72668 (5)0.63168 (5)0.54574 (3)0.02919 (13)
F0.32177 (16)0.21796 (16)0.88301 (12)0.0529 (3)
O10.84077 (14)0.45046 (13)0.92200 (9)0.0247 (2)
O21.01504 (16)0.88467 (14)0.73052 (13)0.0368 (3)
O30.73837 (17)0.89429 (16)0.69571 (14)0.0428 (3)
O40.74634 (18)0.50040 (17)0.47717 (11)0.0422 (3)
C70.7124 (2)0.38103 (18)0.92490 (14)0.0246 (3)
C10.7324 (2)0.53985 (18)0.71812 (13)0.0235 (3)
C20.6385 (2)0.43348 (18)0.80110 (14)0.0236 (3)
C30.5036 (2)0.3785 (2)0.78410 (16)0.0296 (3)
H30.45040.41090.70350.036*
C40.4545 (2)0.2735 (2)0.89391 (18)0.0342 (4)
C50.5303 (2)0.2183 (2)1.01700 (17)0.0350 (4)
H50.49250.14501.08660.042*
C60.6629 (2)0.2741 (2)1.03413 (15)0.0301 (3)
H60.71570.24121.11490.036*
C80.8506 (2)0.54532 (18)0.79478 (13)0.0228 (3)
C90.9836 (2)0.63165 (18)0.76654 (14)0.0254 (3)
H9A1.07460.59420.69460.030*
H9B1.04890.60120.84560.030*
C100.8940 (2)0.81678 (19)0.72758 (14)0.0268 (3)
C110.9500 (3)1.0649 (2)0.6923 (2)0.0499 (5)
H11A0.82651.11200.73460.060*
H11B0.94561.10290.59590.060*
C121.0827 (3)1.1155 (2)0.7373 (2)0.0458 (4)
H12A1.20451.06770.69520.055*
H12B1.08501.07810.83290.055*
H12C1.04411.23330.71300.055*
C130.4872 (2)0.7641 (2)0.54508 (17)0.0385 (4)
H13A0.46220.83050.45630.058*
H13B0.46030.83410.60590.058*
H13C0.41080.69880.57270.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0300 (2)0.0380 (3)0.01935 (19)0.01155 (17)0.00708 (14)0.00428 (15)
F0.0482 (6)0.0562 (8)0.0708 (8)0.0359 (6)0.0137 (6)0.0093 (6)
O10.0298 (5)0.0263 (5)0.0213 (5)0.0122 (4)0.0090 (4)0.0032 (4)
O20.0328 (6)0.0229 (6)0.0573 (7)0.0104 (5)0.0141 (5)0.0059 (5)
O30.0347 (6)0.0308 (7)0.0608 (8)0.0108 (5)0.0202 (6)0.0016 (6)
O40.0430 (7)0.0561 (9)0.0291 (6)0.0093 (6)0.0085 (5)0.0218 (5)
C70.0259 (7)0.0238 (7)0.0261 (7)0.0083 (6)0.0063 (5)0.0073 (5)
C10.0262 (7)0.0247 (7)0.0208 (6)0.0073 (6)0.0067 (5)0.0065 (5)
C20.0241 (7)0.0229 (7)0.0245 (7)0.0057 (6)0.0058 (5)0.0082 (5)
C30.0274 (7)0.0308 (8)0.0346 (8)0.0092 (6)0.0089 (6)0.0118 (6)
C40.0297 (8)0.0324 (9)0.0480 (9)0.0156 (7)0.0057 (7)0.0126 (7)
C50.0360 (9)0.0291 (8)0.0397 (9)0.0154 (7)0.0015 (7)0.0035 (7)
C60.0349 (8)0.0271 (8)0.0275 (7)0.0114 (7)0.0063 (6)0.0024 (6)
C80.0259 (7)0.0219 (7)0.0209 (6)0.0072 (6)0.0056 (5)0.0050 (5)
C90.0248 (7)0.0252 (8)0.0275 (7)0.0086 (6)0.0077 (5)0.0052 (5)
C100.0285 (7)0.0274 (8)0.0258 (7)0.0112 (6)0.0058 (6)0.0043 (6)
C110.0485 (11)0.0228 (9)0.0790 (14)0.0104 (8)0.0232 (10)0.0047 (9)
C120.0414 (10)0.0269 (9)0.0701 (13)0.0142 (8)0.0037 (9)0.0109 (8)
C130.0342 (8)0.0366 (10)0.0365 (9)0.0027 (7)0.0147 (7)0.0031 (7)
Geometric parameters (Å, º) top
S—O41.5007 (13)C5—C61.387 (2)
S—C11.7583 (14)C5—H50.9300
S—C131.7914 (18)C6—H60.9300
F—C41.3633 (17)C8—C91.4859 (19)
O1—C81.3723 (17)C9—C101.509 (2)
O1—C71.3813 (16)C9—H9A0.9700
O2—C101.3343 (17)C9—H9B0.9700
O2—C111.466 (2)C11—C121.488 (3)
O3—C101.2035 (19)C11—H11A0.9700
C7—C61.381 (2)C11—H11B0.9700
C7—C21.3972 (19)C12—H12A0.9600
C1—C81.3603 (19)C12—H12B0.9600
C1—C21.446 (2)C12—H12C0.9600
C2—C31.3984 (19)C13—H13A0.9600
C3—C41.373 (2)C13—H13B0.9600
C3—H30.9300C13—H13C0.9600
C4—C51.396 (2)
O4—S—C1106.41 (7)O1—C8—C9116.26 (11)
O4—S—C13106.04 (8)C8—C9—C10113.99 (12)
C1—S—C1398.86 (8)C8—C9—H9A108.8
C8—O1—C7106.33 (10)C10—C9—H9A108.8
C10—O2—C11116.58 (13)C8—C9—H9B108.8
C6—C7—O1125.26 (12)C10—C9—H9B108.8
C6—C7—C2124.13 (13)H9A—C9—H9B107.6
O1—C7—C2110.62 (12)O3—C10—O2123.99 (15)
C8—C1—C2107.22 (12)O3—C10—C9126.12 (13)
C8—C1—S122.68 (11)O2—C10—C9109.88 (12)
C2—C1—S129.73 (10)O2—C11—C12107.55 (15)
C7—C2—C3119.44 (13)O2—C11—H11A110.2
C7—C2—C1104.72 (12)C12—C11—H11A110.2
C3—C2—C1135.84 (13)O2—C11—H11B110.2
C4—C3—C2115.78 (14)C12—C11—H11B110.2
C4—C3—H3122.1H11A—C11—H11B108.5
C2—C3—H3122.1C11—C12—H12A109.5
F—C4—C3118.07 (14)C11—C12—H12B109.5
F—C4—C5116.90 (15)H12A—C12—H12B109.5
C3—C4—C5125.04 (14)C11—C12—H12C109.5
C6—C5—C4119.12 (15)H12A—C12—H12C109.5
C6—C5—H5120.4H12B—C12—H12C109.5
C4—C5—H5120.4S—C13—H13A109.5
C7—C6—C5116.48 (14)S—C13—H13B109.5
C7—C6—H6121.8H13A—C13—H13B109.5
C5—C6—H6121.8S—C13—H13C109.5
C1—C8—O1111.11 (12)H13A—C13—H13C109.5
C1—C8—C9132.64 (13)H13B—C13—H13C109.5
C8—O1—C7—C6178.81 (15)F—C4—C5—C6178.60 (15)
C8—O1—C7—C21.02 (16)C3—C4—C5—C61.5 (3)
O4—S—C1—C8127.12 (13)O1—C7—C6—C5179.74 (15)
C13—S—C1—C8123.16 (14)C2—C7—C6—C50.4 (2)
O4—S—C1—C245.00 (15)C4—C5—C6—C70.8 (2)
C13—S—C1—C264.72 (15)C2—C1—C8—O10.08 (17)
C6—C7—C2—C31.0 (2)S—C1—C8—O1173.75 (10)
O1—C7—C2—C3179.12 (13)C2—C1—C8—C9179.69 (15)
C6—C7—C2—C1178.88 (14)S—C1—C8—C96.0 (2)
O1—C7—C2—C10.96 (16)C7—O1—C8—C10.67 (16)
C8—C1—C2—C70.53 (16)C7—O1—C8—C9179.15 (12)
S—C1—C2—C7172.54 (12)C1—C8—C9—C1061.4 (2)
C8—C1—C2—C3179.57 (17)O1—C8—C9—C10118.84 (14)
S—C1—C2—C37.4 (3)C11—O2—C10—O30.1 (2)
C7—C2—C3—C40.4 (2)C11—O2—C10—C9178.79 (15)
C1—C2—C3—C4179.54 (16)C8—C9—C10—O313.8 (2)
C2—C3—C4—F179.21 (14)C8—C9—C10—O2167.56 (12)
C2—C3—C4—C50.9 (3)C10—O2—C11—C12164.80 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O4i0.932.423.3374 (19)168
C5—H5···O3ii0.932.673.482 (2)147
C9—H9A···O4iii0.972.213.177 (2)172
C9—H9B···O1iv0.972.593.542 (2)169
C11—H11A···Cg2v0.972.923.773 (2)148
C12—H12C···Cg1v0.972.813.502 (2)129
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z+2; (iii) x+2, y+1, z+1; (iv) x+2, y+1, z+2; (v) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC13H13FO4S
Mr284.29
Crystal system, space groupTriclinic, P1
Temperature (K)273
a, b, c (Å)7.8821 (5), 9.0922 (5), 10.4354 (6)
α, β, γ (°)73.682 (1), 79.155 (1), 66.622 (1)
V3)656.31 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.40 × 0.40 × 0.10
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5673, 2805, 2512
Rint0.063
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.101, 1.04
No. of reflections2805
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.35

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O4i0.932.423.3374 (19)168.2
C5—H5···O3ii0.932.673.482 (2)147.1
C9—H9A···O4iii0.972.213.177 (2)172.2
C9—H9B···O1iv0.972.593.542 (2)168.7
C11—H11A···Cg2v0.972.923.773 (2)147.8
C12—H12C···Cg1v0.972.813.502 (2)129.4
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z+2; (iii) x+2, y+1, z+1; (iv) x+2, y+1, z+2; (v) x, y+1, z.
 

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