organic compounds
of 5-chloro-2-(2-fluorophenyl)-3-methylsulfinyl-1-benzofuran
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
In the title compound, C15H10ClFO2S, the dihedral angle between the mean planes of the benzofuran ring [r.m.s. deviation = 0.007 (1) Å] and the 2-fluorophenyl ring is 32.53 (5)°. In the crystal, molecules related by inversion are paired into dimers via two different C—H⋯O hydrogen bonds. Further, Cl⋯O halogen bonds [3.114 (1) Å], and F⋯π [F-to-furan-centroid distance = 3.109 (1) Å] and S⋯F [3.1984 (9) Å] interactions link these into a three-dimensional network.
Keywords: crystal structure; benzofuran; 2-fluorophenyl; C—H⋯O hydrogen bonds; F⋯π and S⋯F contacts.
CCDC reference: 1414408
1. Related literature
For the pharmacological properties of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Wahab Khan et al. (2005); Ono et al. (2002). For a related structure, see: Choi & Lee (2014). For further synthetic details, see: Choi et al. (1999). For a review of halogen bonding, see: Politzer et al. (2007).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL2014.
Supporting information
CCDC reference: 1414408
https://doi.org/10.1107/S2056989015013948/fy2120sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015013948/fy2120Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015013948/fy2120Isup3.cml
The starting material 5-chloro-2-(2-fluorophenyl)-3-methylsulfanyl-1-benzofuran was prepared by a literature method (Choi et al., 1999). 3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-chloro-2-(2-fluorophenyl)-3-methylsulfanyl-1-benzofuran (263 mg, 0.9 mmol) in dichloromethane (25 ml) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with saturated sodium bicarbonate solution (2 × 10 ml) and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by
(hexane-ethyl acetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 68% (188 mg); m.p. 431-432 K; Rf = 0.55 (hexane-ethyl acetate, 1:2 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound (18 mg) in ethyl acetate (20 ml) at room temperature.All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aryl and 0.98 Å for methyl H atoms and Uiso (H) = 1.2Ueq (C) for aryl and 1.5Ueq (C) for methyl H atoms. The positions of methyl hydrogens were optimized using the SHELXL-2014/7 command AFIX 137 (Sheldrick, 2015).
Many compounds involving a benzofuran ring show significant pharmacological properties, such as antibacterial, antifungal, antitumor, antiviral and antimicrobial activities (Aslam et al. 2009; Galal et al., 2009; Wahab Khan et al., 2005), and are potential inhibitors of β-amyloid aggregation (Howlett et al., 1999; Ono et al., 2002). As a part of our continuing project on benzofuran derivatives (Choi & Lee, 2014), we report herein the of the title compound.
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The 2-fluorophenyl ring is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring and the 2-fluorophenyl ring is 32.53 (5)°. In the ═O unit [Cl1···O2iii = 3.114 (1) Å, C4–Cl1···O2iii = 171.16 (5)°] (Politzer et al., 2007), F1···Cgv [3.109 (1) Å] (Cg is the centroid of the C1/C2/C7/O1/C8 furan ring) and S1···F1iv [3.1984 (9) Å] interactions, forming a three–dimensional network. [Symmetry codes: (i) - x + 2, - y + 1, - z; (ii) - x + 1, - y + 1, - z; (iii) - x + 1 , - y + 1, - z + 1; (iv) - x, - y, - z ; (v) - x + 1, - y, - z.]
(Fig. 2), molecules related by inversion are paired into dimers via two different C–H···O hydrogen bonds (Table 1), and a Cl···O halogen bond between the chlorine and the oxygen of the SFor the pharmacological properties of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Howlett et al. (1999); Wahab Khan et al. (2005); Ono et al. (2002). For a related structure, see: Choi & Lee (2014). For further synthetic details, see: Choi et al. (1999). For a review of halogen bonding, see: Politzer et al. (2007).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).C15H10ClFO2S | Z = 2 |
Mr = 308.74 | F(000) = 316 |
Triclinic, P1 | Dx = 1.570 Mg m−3 |
a = 7.9626 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.3518 (1) Å | Cell parameters from 6796 reflections |
c = 10.7127 (2) Å | θ = 2.7–28.4° |
α = 92.758 (1)° | µ = 0.46 mm−1 |
β = 95.509 (1)° | T = 173 K |
γ = 112.373 (1)° | Block, colourless |
V = 652.97 (2) Å3 | 0.45 × 0.36 × 0.32 mm |
Bruker SMART APEXII CCD diffractometer | 3263 independent reflections |
Radiation source: rotating anode | 3030 reflections with I > 2σ(I) |
Detector resolution: 10.0 pixels mm-1 | Rint = 0.023 |
φ and ω scans | θmax = 28.4°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −10→10 |
Tmin = 0.690, Tmax = 0.746 | k = −11→11 |
12250 measured reflections | l = −14→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0399P)2 + 0.2911P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3263 reflections | Δρmax = 0.34 e Å−3 |
183 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.042 (3) |
C15H10ClFO2S | γ = 112.373 (1)° |
Mr = 308.74 | V = 652.97 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9626 (1) Å | Mo Kα radiation |
b = 8.3518 (1) Å | µ = 0.46 mm−1 |
c = 10.7127 (2) Å | T = 173 K |
α = 92.758 (1)° | 0.45 × 0.36 × 0.32 mm |
β = 95.509 (1)° |
Bruker SMART APEXII CCD diffractometer | 3263 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 3030 reflections with I > 2σ(I) |
Tmin = 0.690, Tmax = 0.746 | Rint = 0.023 |
12250 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.34 e Å−3 |
3263 reflections | Δρmin = −0.26 e Å−3 |
183 parameters |
Experimental. 1H NMR (δ p.p.m., CDCl3, 400 Hz): 8.21 (d, J = 2.04 Hz, 1H), 7.66-7.71 (m, 1H), 7.50-7.57 (m, 2H), 7.32-7.41 (m, 2H), 7.21-7.26 (m, 1H), 3.15 (s, 3H). |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.80773 (5) | 0.60679 (5) | 0.52105 (3) | 0.03134 (11) | |
S1 | 0.20658 (4) | 0.19225 (4) | 0.10339 (3) | 0.02090 (10) | |
F1 | 0.22939 (12) | −0.06448 (11) | −0.07604 (8) | 0.0324 (2) | |
O1 | 0.70194 (12) | 0.36314 (12) | −0.00857 (8) | 0.02229 (19) | |
O2 | 0.18502 (13) | 0.32691 (13) | 0.18956 (10) | 0.0283 (2) | |
C1 | 0.44206 (16) | 0.27158 (16) | 0.08330 (11) | 0.0198 (2) | |
C2 | 0.58981 (17) | 0.37914 (16) | 0.17693 (11) | 0.0198 (2) | |
C3 | 0.60633 (18) | 0.43369 (17) | 0.30452 (12) | 0.0220 (3) | |
H3 | 0.5032 | 0.4009 | 0.3498 | 0.026* | |
C4 | 0.77958 (18) | 0.53749 (17) | 0.36158 (12) | 0.0231 (3) | |
C5 | 0.93409 (18) | 0.58960 (18) | 0.29751 (13) | 0.0258 (3) | |
H5 | 1.0502 | 0.6620 | 0.3411 | 0.031* | |
C6 | 0.91896 (18) | 0.53654 (18) | 0.17133 (13) | 0.0255 (3) | |
H6 | 1.0220 | 0.5701 | 0.1260 | 0.031* | |
C7 | 0.74560 (17) | 0.43207 (16) | 0.11491 (12) | 0.0208 (2) | |
C8 | 0.51654 (17) | 0.26585 (16) | −0.02553 (12) | 0.0201 (2) | |
C9 | 0.44641 (17) | 0.17903 (16) | −0.15243 (12) | 0.0210 (2) | |
C10 | 0.30426 (18) | 0.01690 (17) | −0.17542 (13) | 0.0242 (3) | |
C11 | 0.2375 (2) | −0.06907 (19) | −0.29337 (14) | 0.0304 (3) | |
H11 | 0.1390 | −0.1796 | −0.3049 | 0.036* | |
C12 | 0.3186 (2) | 0.0106 (2) | −0.39495 (14) | 0.0341 (3) | |
H12 | 0.2744 | −0.0450 | −0.4778 | 0.041* | |
C13 | 0.4640 (2) | 0.1712 (2) | −0.37641 (13) | 0.0311 (3) | |
H13 | 0.5198 | 0.2238 | −0.4466 | 0.037* | |
C14 | 0.52834 (19) | 0.25528 (17) | −0.25675 (12) | 0.0244 (3) | |
H14 | 0.6282 | 0.3649 | −0.2451 | 0.029* | |
C15 | 0.2029 (2) | 0.02115 (19) | 0.20017 (15) | 0.0323 (3) | |
H15A | 0.2950 | 0.0697 | 0.2741 | 0.048* | |
H15B | 0.2302 | −0.0665 | 0.1516 | 0.048* | |
H15C | 0.0814 | −0.0330 | 0.2276 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.02955 (19) | 0.0403 (2) | 0.02092 (16) | 0.01176 (15) | −0.00124 (12) | −0.00425 (13) |
S1 | 0.01618 (16) | 0.02104 (16) | 0.02386 (16) | 0.00518 (12) | 0.00408 (11) | 0.00099 (11) |
F1 | 0.0333 (5) | 0.0245 (4) | 0.0318 (4) | 0.0018 (3) | 0.0101 (4) | 0.0004 (3) |
O1 | 0.0179 (4) | 0.0253 (4) | 0.0208 (4) | 0.0049 (4) | 0.0045 (3) | 0.0002 (3) |
O2 | 0.0243 (5) | 0.0265 (5) | 0.0342 (5) | 0.0092 (4) | 0.0093 (4) | −0.0024 (4) |
C1 | 0.0168 (6) | 0.0198 (6) | 0.0214 (6) | 0.0054 (4) | 0.0033 (4) | 0.0016 (4) |
C2 | 0.0176 (6) | 0.0194 (6) | 0.0223 (6) | 0.0068 (4) | 0.0031 (4) | 0.0021 (4) |
C3 | 0.0211 (6) | 0.0247 (6) | 0.0212 (6) | 0.0095 (5) | 0.0042 (5) | 0.0024 (5) |
C4 | 0.0245 (6) | 0.0250 (6) | 0.0199 (6) | 0.0102 (5) | 0.0007 (5) | 0.0000 (5) |
C5 | 0.0191 (6) | 0.0268 (6) | 0.0270 (6) | 0.0054 (5) | −0.0012 (5) | −0.0009 (5) |
C6 | 0.0185 (6) | 0.0280 (7) | 0.0274 (6) | 0.0056 (5) | 0.0054 (5) | 0.0017 (5) |
C7 | 0.0200 (6) | 0.0216 (6) | 0.0201 (5) | 0.0069 (5) | 0.0041 (4) | 0.0014 (4) |
C8 | 0.0174 (6) | 0.0188 (5) | 0.0232 (6) | 0.0057 (4) | 0.0032 (4) | 0.0022 (4) |
C9 | 0.0213 (6) | 0.0221 (6) | 0.0213 (6) | 0.0104 (5) | 0.0028 (5) | −0.0004 (4) |
C10 | 0.0230 (6) | 0.0235 (6) | 0.0265 (6) | 0.0092 (5) | 0.0051 (5) | 0.0009 (5) |
C11 | 0.0286 (7) | 0.0263 (7) | 0.0319 (7) | 0.0083 (6) | −0.0015 (6) | −0.0066 (5) |
C12 | 0.0409 (9) | 0.0368 (8) | 0.0247 (7) | 0.0177 (7) | −0.0020 (6) | −0.0067 (6) |
C13 | 0.0395 (8) | 0.0347 (7) | 0.0221 (6) | 0.0176 (6) | 0.0047 (6) | 0.0025 (5) |
C14 | 0.0259 (6) | 0.0244 (6) | 0.0240 (6) | 0.0106 (5) | 0.0048 (5) | 0.0027 (5) |
C15 | 0.0310 (7) | 0.0285 (7) | 0.0386 (8) | 0.0097 (6) | 0.0134 (6) | 0.0126 (6) |
Cl1—C4 | 1.7425 (13) | C6—C7 | 1.3800 (18) |
S1—O2 | 1.4913 (10) | C6—H6 | 0.9500 |
S1—C1 | 1.7739 (12) | C8—C9 | 1.4618 (17) |
S1—C15 | 1.7983 (14) | C9—C10 | 1.3867 (18) |
F1—C10 | 1.3542 (15) | C9—C14 | 1.4043 (18) |
O1—C7 | 1.3741 (15) | C10—C11 | 1.3740 (19) |
O1—C8 | 1.3762 (15) | C11—C12 | 1.386 (2) |
C1—C8 | 1.3647 (17) | C11—H11 | 0.9500 |
C1—C2 | 1.4420 (17) | C12—C13 | 1.388 (2) |
C2—C7 | 1.3945 (17) | C12—H12 | 0.9500 |
C2—C3 | 1.3976 (17) | C13—C14 | 1.3830 (19) |
C3—C4 | 1.3802 (18) | C13—H13 | 0.9500 |
C3—H3 | 0.9500 | C14—H14 | 0.9500 |
C4—C5 | 1.3990 (19) | C15—H15A | 0.9800 |
C5—C6 | 1.3815 (19) | C15—H15B | 0.9800 |
C5—H5 | 0.9500 | C15—H15C | 0.9800 |
O2—S1—C1 | 105.84 (6) | C1—C8—C9 | 135.10 (12) |
O2—S1—C15 | 105.10 (7) | O1—C8—C9 | 114.01 (10) |
C1—S1—C15 | 97.80 (6) | C10—C9—C14 | 117.07 (12) |
C7—O1—C8 | 106.59 (9) | C10—C9—C8 | 122.54 (12) |
C8—C1—C2 | 106.80 (11) | C14—C9—C8 | 120.32 (12) |
C8—C1—S1 | 127.53 (10) | F1—C10—C11 | 117.65 (12) |
C2—C1—S1 | 125.04 (9) | F1—C10—C9 | 118.49 (12) |
C7—C2—C3 | 119.16 (11) | C11—C10—C9 | 123.83 (13) |
C7—C2—C1 | 105.31 (11) | C10—C11—C12 | 117.90 (14) |
C3—C2—C1 | 135.52 (12) | C10—C11—H11 | 121.1 |
C4—C3—C2 | 116.81 (12) | C12—C11—H11 | 121.0 |
C4—C3—H3 | 121.6 | C11—C12—C13 | 120.39 (13) |
C2—C3—H3 | 121.6 | C11—C12—H12 | 119.8 |
C3—C4—C5 | 123.12 (12) | C13—C12—H12 | 119.8 |
C3—C4—Cl1 | 118.55 (10) | C14—C13—C12 | 120.60 (13) |
C5—C4—Cl1 | 118.33 (10) | C14—C13—H13 | 119.7 |
C6—C5—C4 | 120.45 (12) | C12—C13—H13 | 119.7 |
C6—C5—H5 | 119.8 | C13—C14—C9 | 120.18 (13) |
C4—C5—H5 | 119.8 | C13—C14—H14 | 119.9 |
C7—C6—C5 | 116.19 (12) | C9—C14—H14 | 119.9 |
C7—C6—H6 | 121.9 | S1—C15—H15A | 109.5 |
C5—C6—H6 | 121.9 | S1—C15—H15B | 109.5 |
O1—C7—C6 | 125.31 (11) | H15A—C15—H15B | 109.5 |
O1—C7—C2 | 110.42 (11) | S1—C15—H15C | 109.5 |
C6—C7—C2 | 124.26 (12) | H15A—C15—H15C | 109.5 |
C1—C8—O1 | 110.87 (11) | H15B—C15—H15C | 109.5 |
O2—S1—C1—C8 | −138.17 (12) | C1—C2—C7—C6 | −179.34 (12) |
C15—S1—C1—C8 | 113.63 (13) | C2—C1—C8—O1 | −0.33 (14) |
O2—S1—C1—C2 | 31.48 (12) | S1—C1—C8—O1 | 170.83 (9) |
C15—S1—C1—C2 | −76.71 (12) | C2—C1—C8—C9 | 178.19 (13) |
C8—C1—C2—C7 | 0.43 (14) | S1—C1—C8—C9 | −10.6 (2) |
S1—C1—C2—C7 | −171.01 (9) | C7—O1—C8—C1 | 0.10 (14) |
C8—C1—C2—C3 | −178.84 (14) | C7—O1—C8—C9 | −178.76 (10) |
S1—C1—C2—C3 | 9.7 (2) | C1—C8—C9—C10 | −33.0 (2) |
C7—C2—C3—C4 | −0.38 (18) | O1—C8—C9—C10 | 145.51 (12) |
C1—C2—C3—C4 | 178.82 (13) | C1—C8—C9—C14 | 150.06 (15) |
C2—C3—C4—C5 | 0.61 (19) | O1—C8—C9—C14 | −31.45 (17) |
C2—C3—C4—Cl1 | −179.26 (9) | C14—C9—C10—F1 | 176.27 (11) |
C3—C4—C5—C6 | −0.5 (2) | C8—C9—C10—F1 | −0.78 (19) |
Cl1—C4—C5—C6 | 179.35 (11) | C14—C9—C10—C11 | −1.8 (2) |
C4—C5—C6—C7 | 0.2 (2) | C8—C9—C10—C11 | −178.88 (13) |
C8—O1—C7—C6 | 179.14 (12) | F1—C10—C11—C12 | −177.47 (13) |
C8—O1—C7—C2 | 0.19 (14) | C9—C10—C11—C12 | 0.6 (2) |
C5—C6—C7—O1 | −178.76 (12) | C10—C11—C12—C13 | 0.8 (2) |
C5—C6—C7—C2 | 0.0 (2) | C11—C12—C13—C14 | −1.0 (2) |
C3—C2—C7—O1 | 179.03 (11) | C12—C13—C14—C9 | −0.2 (2) |
C1—C2—C7—O1 | −0.39 (14) | C10—C9—C14—C13 | 1.59 (19) |
C3—C2—C7—C6 | 0.1 (2) | C8—C9—C14—C13 | 178.71 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.95 | 2.53 | 3.4756 (16) | 176 |
C14—H14···O2ii | 0.95 | 2.44 | 3.3591 (17) | 163 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.95 | 2.53 | 3.4756 (16) | 175.5 |
C14—H14···O2ii | 0.95 | 2.44 | 3.3591 (17) | 162.5 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z. |
Acknowledgements
The X-ray centre of the Gyeongsang National University is acknowledged for providing access to the single-crystal diffractometer.
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Many compounds involving a benzofuran ring show significant pharmacological properties, such as antibacterial, antifungal, antitumor, antiviral and antimicrobial activities (Aslam et al. 2009; Galal et al., 2009; Wahab Khan et al., 2005), and are potential inhibitors of β-amyloid aggregation (Howlett et al., 1999; Ono et al., 2002). As a part of our continuing project on benzofuran derivatives (Choi & Lee, 2014), we report herein the crystal structure of the title compound.
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the nine constituent atoms. The 2-fluorophenyl ring is essentially planar, with a mean deviation of 0.007 (1) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring and the 2-fluorophenyl ring is 32.53 (5)°. In the crystal structure (Fig. 2), molecules related by inversion are paired into dimers via two different C–H···O hydrogen bonds (Table 1), and a Cl···O halogen bond between the chlorine and the oxygen of the S═O unit [Cl1···O2iii = 3.114 (1) Å, C4–Cl1···O2iii = 171.16 (5)°] (Politzer et al., 2007), F1···Cgv [3.109 (1) Å] (Cg is the centroid of the C1/C2/C7/O1/C8 furan ring) and S1···F1iv [3.1984 (9) Å] interactions, forming a three–dimensional network. [Symmetry codes: (i) - x + 2, - y + 1, - z; (ii) - x + 1, - y + 1, - z; (iii) - x + 1 , - y + 1, - z + 1; (iv) - x, - y, - z ; (v) - x + 1, - y, - z.]