Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101020911/tr1006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101020911/tr1006Isup2.hkl |
CCDC reference: 182000
Solutions of antimony trichloride (0.320 g, 1.40 mmol) and trimethylenethiourea (0.325 g, 0.28 mmol) in a 1:2 molar ratio in acetonitrile were mixed in a 50 ml flask and stirred for about 30 min. The solution was then filtered and left to slowly evaporate. After three days, single crystals were collected (yield 62%), washed with hexane and dried before subjected to X-ray crystallographic analysis.
After checking their presence in a difference map, all the H atoms were fixed geometrically and allowed to ride on their attached atoms (N—H = 0.86 Å and C—H = 0.97 Å). The highest peak and the deepest hole were found near the Sb1 atom at distances of 0.94 and 1.12 Å, respectively.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
[SbCl2(C4H8N2S)2]Cl | F(000) = 452 |
Mr = 460.47 | Dx = 1.789 Mg m−3 |
Triclinic, P1 | Melting point: 480K K |
a = 7.5103 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3304 (5) Å | Cell parameters from 5944 reflections |
c = 12.1206 (6) Å | θ = 1.8–29.4° |
α = 71.358 (1)° | µ = 2.32 mm−1 |
β = 84.252 (1)° | T = 293 K |
γ = 73.612 (1)° | Block, colourless |
V = 854.78 (7) Å3 | 0.20 × 0.16 × 0.14 mm |
Z = 2 |
Siemens SMART CCD area-detector diffractometer | 2981 independent reflections |
Radiation source: fine-focus sealed tube | 2799 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
ω scans | h = −7→8 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −12→9 |
Tmin = 0.655, Tmax = 0.738 | l = −14→14 |
4916 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.058 | H-atom parameters constrained |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.0841P)2 + 0.1942P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
2981 reflections | Δρmax = 1.55 e Å−3 |
164 parameters | Δρmin = −1.79 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.054 (5) |
[SbCl2(C4H8N2S)2]Cl | γ = 73.612 (1)° |
Mr = 460.47 | V = 854.78 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5103 (4) Å | Mo Kα radiation |
b = 10.3304 (5) Å | µ = 2.32 mm−1 |
c = 12.1206 (6) Å | T = 293 K |
α = 71.358 (1)° | 0.20 × 0.16 × 0.14 mm |
β = 84.252 (1)° |
Siemens SMART CCD area-detector diffractometer | 2981 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 2799 reflections with I > 2σ(I) |
Tmin = 0.655, Tmax = 0.738 | Rint = 0.069 |
4916 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.09 | Δρmax = 1.55 e Å−3 |
2981 reflections | Δρmin = −1.79 e Å−3 |
164 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating thirty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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. |
x | y | z | Uiso*/Ueq | ||
Sb1 | 0.47852 (4) | 0.44234 (3) | 0.19963 (3) | 0.0272 (3) | |
Cl1 | 0.4838 (2) | 0.18669 (15) | 0.29632 (14) | 0.0460 (4) | |
Cl2 | 0.3689 (2) | 0.72354 (15) | 0.10677 (14) | 0.0461 (4) | |
Cl3 | 0.7829 (2) | 0.4118 (2) | 0.35724 (15) | 0.0479 (4) | |
S1 | 0.26511 (19) | 0.51998 (14) | 0.34993 (11) | 0.0341 (4) | |
S2 | 0.2109 (2) | 0.48201 (15) | 0.06763 (13) | 0.0375 (4) | |
N1 | 0.1543 (7) | 0.3125 (6) | 0.5067 (4) | 0.0413 (12) | |
H1A | 0.0530 | 0.3510 | 0.4680 | 0.050* | |
N2 | 0.4532 (6) | 0.3148 (5) | 0.5265 (4) | 0.0358 (11) | |
H2A | 0.5421 | 0.3542 | 0.5007 | 0.043* | |
N3 | 0.2613 (8) | 0.2301 (6) | 0.0380 (4) | 0.0448 (13) | |
H3A | 0.3356 | 0.2599 | −0.0168 | 0.054* | |
N4 | 0.0529 (7) | 0.2768 (6) | 0.1814 (5) | 0.0429 (12) | |
H4A | −0.0075 | 0.3366 | 0.2165 | 0.051* | |
C1 | 0.2965 (7) | 0.3667 (6) | 0.4709 (4) | 0.0299 (11) | |
C2 | 0.4834 (10) | 0.1917 (7) | 0.6314 (6) | 0.0508 (16) | |
H2B | 0.5696 | 0.1990 | 0.6822 | 0.061* | |
H2C | 0.5362 | 0.1056 | 0.6102 | 0.061* | |
C3 | 0.3020 (12) | 0.1866 (8) | 0.6930 (6) | 0.058 (2) | |
H3B | 0.2569 | 0.2670 | 0.7226 | 0.070* | |
H3C | 0.3184 | 0.1007 | 0.7586 | 0.070* | |
C4 | 0.1618 (10) | 0.1896 (8) | 0.6098 (6) | 0.0548 (18) | |
H4B | 0.1985 | 0.1033 | 0.5877 | 0.066* | |
H4C | 0.0405 | 0.1962 | 0.6471 | 0.066* | |
C5 | 0.1724 (7) | 0.3149 (6) | 0.1001 (4) | 0.0311 (11) | |
C6 | 0.0166 (12) | 0.1354 (9) | 0.2161 (8) | 0.067 (2) | |
H6A | 0.0922 | 0.0730 | 0.2826 | 0.081* | |
H6B | −0.1127 | 0.1439 | 0.2389 | 0.081* | |
C7 | 0.0592 (13) | 0.0744 (9) | 0.1201 (9) | 0.077 (3) | |
H7A | −0.0404 | 0.1201 | 0.0640 | 0.093* | |
H7B | 0.0633 | −0.0254 | 0.1500 | 0.093* | |
C8 | 0.2382 (13) | 0.0891 (8) | 0.0592 (8) | 0.068 (3) | |
H8A | 0.3400 | 0.0196 | 0.1061 | 0.082* | |
H8B | 0.2422 | 0.0701 | −0.0145 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sb1 | 0.0260 (3) | 0.0231 (3) | 0.0318 (3) | −0.00468 (19) | 0.00005 (18) | −0.0094 (2) |
Cl1 | 0.0568 (10) | 0.0221 (7) | 0.0557 (9) | −0.0049 (6) | −0.0151 (7) | −0.0078 (6) |
Cl2 | 0.0515 (10) | 0.0259 (7) | 0.0568 (9) | −0.0125 (7) | 0.0074 (7) | −0.0075 (6) |
Cl3 | 0.0249 (8) | 0.0723 (11) | 0.0598 (10) | −0.0116 (7) | 0.0029 (6) | −0.0403 (9) |
S1 | 0.0322 (8) | 0.0289 (7) | 0.0337 (7) | 0.0006 (6) | 0.0011 (6) | −0.0075 (6) |
S2 | 0.0456 (9) | 0.0260 (7) | 0.0404 (8) | −0.0052 (6) | −0.0173 (6) | −0.0082 (6) |
N1 | 0.029 (3) | 0.042 (3) | 0.048 (3) | −0.011 (2) | −0.002 (2) | −0.006 (2) |
N2 | 0.030 (3) | 0.036 (3) | 0.038 (2) | −0.008 (2) | −0.0100 (19) | −0.005 (2) |
N3 | 0.054 (3) | 0.046 (3) | 0.046 (3) | −0.021 (3) | 0.014 (2) | −0.026 (2) |
N4 | 0.045 (3) | 0.035 (3) | 0.053 (3) | −0.013 (2) | 0.005 (2) | −0.019 (2) |
C1 | 0.026 (3) | 0.032 (3) | 0.033 (3) | −0.009 (2) | 0.001 (2) | −0.013 (2) |
C2 | 0.066 (4) | 0.037 (3) | 0.050 (3) | −0.017 (3) | −0.021 (3) | −0.007 (3) |
C3 | 0.084 (6) | 0.039 (4) | 0.040 (3) | −0.014 (4) | −0.001 (4) | 0.001 (3) |
C4 | 0.054 (4) | 0.046 (4) | 0.058 (4) | −0.021 (3) | 0.014 (3) | −0.005 (3) |
C5 | 0.031 (3) | 0.036 (3) | 0.032 (3) | −0.006 (2) | −0.006 (2) | −0.019 (2) |
C6 | 0.062 (5) | 0.052 (4) | 0.096 (6) | −0.030 (4) | 0.021 (4) | −0.027 (4) |
C7 | 0.082 (6) | 0.050 (5) | 0.113 (7) | −0.036 (5) | 0.017 (5) | −0.032 (5) |
C8 | 0.097 (7) | 0.043 (4) | 0.082 (5) | −0.034 (4) | 0.038 (5) | −0.041 (4) |
Sb1—S1 | 2.481 (1) | N4—H4A | 0.8600 |
Sb1—S2 | 2.555 (2) | C2—C3 | 1.492 (11) |
Sb1—Cl1 | 2.514 (1) | C2—H2B | 0.9700 |
Sb1—Cl2 | 2.670 (2) | C2—H2C | 0.9700 |
S1—C1 | 1.757 (5) | C3—C4 | 1.517 (11) |
S2—C5 | 1.745 (6) | C3—H3B | 0.9700 |
N1—C1 | 1.316 (7) | C3—H3C | 0.9700 |
N1—C4 | 1.462 (8) | C4—H4B | 0.9700 |
N1—H1A | 0.8600 | C4—H4C | 0.9700 |
N2—C1 | 1.303 (7) | C6—C7 | 1.461 (13) |
N2—C2 | 1.465 (8) | C6—H6A | 0.9700 |
N2—H2A | 0.8600 | C6—H6B | 0.9700 |
N3—C5 | 1.330 (7) | C7—C8 | 1.490 (12) |
N3—C8 | 1.453 (9) | C7—H7A | 0.9700 |
N3—H3A | 0.8600 | C7—H7B | 0.9700 |
N4—C5 | 1.306 (7) | C8—H8A | 0.9700 |
N4—C6 | 1.481 (9) | C8—H8B | 0.9700 |
S1—Sb1—Cl1 | 92.41 (5) | C4—C3—H3B | 109.7 |
S1—Sb1—Cl2 | 76.62 (5) | C2—C3—H3C | 109.7 |
S1—Sb1—S2 | 92.59 (5) | C4—C3—H3C | 109.7 |
S2—Sb1—Cl2 | 76.18 (5) | H3B—C3—H3C | 108.2 |
Cl1—Sb1—S2 | 92.43 (5) | N1—C4—C3 | 108.3 (6) |
Cl1—Sb1—Cl2 | 163.60 (6) | N1—C4—H4B | 110.0 |
C1—S1—Sb1 | 104.01 (18) | C3—C4—H4B | 110.0 |
C5—S2—Sb1 | 104.18 (18) | N1—C4—H4C | 110.0 |
C1—N1—C4 | 122.6 (5) | C3—C4—H4C | 110.0 |
C1—N1—H1A | 118.7 | H4B—C4—H4C | 108.4 |
C4—N1—H1A | 118.7 | N4—C5—N3 | 121.1 (5) |
C1—N2—C2 | 122.4 (5) | N4—C5—S2 | 120.0 (4) |
C1—N2—H2A | 118.8 | N3—C5—S2 | 118.9 (4) |
C2—N2—H2A | 118.8 | C7—C6—N4 | 110.7 (6) |
C5—N3—C8 | 122.7 (5) | C7—C6—H6A | 109.5 |
C5—N3—H3A | 118.7 | N4—C6—H6A | 109.5 |
C8—N3—H3A | 118.7 | C7—C6—H6B | 109.5 |
C5—N4—C6 | 123.1 (5) | N4—C6—H6B | 109.5 |
C5—N4—H4A | 118.4 | H6A—C6—H6B | 108.1 |
C6—N4—H4A | 118.4 | C6—C7—C8 | 113.8 (7) |
N2—C1—N1 | 121.8 (5) | C6—C7—H7A | 108.8 |
N2—C1—S1 | 120.1 (4) | C8—C7—H7A | 108.8 |
N1—C1—S1 | 117.9 (4) | C6—C7—H7B | 108.8 |
N2—C2—C3 | 109.0 (5) | C8—C7—H7B | 108.8 |
N2—C2—H2B | 109.9 | H7A—C7—H7B | 107.7 |
C3—C2—H2B | 109.9 | N3—C8—C7 | 111.7 (6) |
N2—C2—H2C | 109.9 | N3—C8—H8A | 109.3 |
C3—C2—H2C | 109.9 | C7—C8—H8A | 109.3 |
H2B—C2—H2C | 108.3 | N3—C8—H8B | 109.3 |
C2—C3—C4 | 109.8 (6) | C7—C8—H8B | 109.3 |
C2—C3—H3B | 109.7 | H8A—C8—H8B | 107.9 |
Cl1—Sb1—S1—C1 | 22.28 (19) | N2—C2—C3—C4 | 54.1 (7) |
S2—Sb1—S1—C1 | 114.82 (19) | C1—N1—C4—C3 | 27.9 (9) |
Cl2—Sb1—S1—C1 | −170.04 (19) | C2—C3—C4—N1 | −53.7 (8) |
S1—Sb1—S2—C5 | −96.33 (19) | C6—N4—C5—N3 | 4.2 (10) |
Cl1—Sb1—S2—C5 | −3.81 (19) | C6—N4—C5—S2 | −178.2 (5) |
Cl2—Sb1—S2—C5 | −171.87 (19) | C8—N3—C5—N4 | −2.6 (10) |
C2—N2—C1—N1 | 0.9 (9) | C8—N3—C5—S2 | 179.8 (6) |
C2—N2—C1—S1 | 176.8 (4) | Sb1—S2—C5—N4 | 91.1 (5) |
C4—N1—C1—N2 | −0.9 (9) | Sb1—S2—C5—N3 | −91.3 (5) |
C4—N1—C1—S1 | −176.9 (5) | C5—N4—C6—C7 | −25.8 (10) |
Sb1—S1—C1—N2 | 68.2 (5) | N4—C6—C7—C8 | 44.9 (11) |
Sb1—S1—C1—N1 | −115.7 (4) | C5—N3—C8—C7 | 22.5 (11) |
C1—N2—C2—C3 | −28.5 (8) | C6—C7—C8—N3 | −44.0 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl3i | 0.86 | 2.37 | 3.213 (6) | 169 |
N2—H2A···Cl3 | 0.86 | 2.44 | 3.227 (5) | 152 |
N3—H3A···Cl2ii | 0.86 | 2.40 | 3.203 (6) | 156 |
N4—H4A···Cl3i | 0.86 | 2.37 | 3.168 (6) | 155 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [SbCl2(C4H8N2S)2]Cl |
Mr | 460.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.5103 (4), 10.3304 (5), 12.1206 (6) |
α, β, γ (°) | 71.358 (1), 84.252 (1), 73.612 (1) |
V (Å3) | 854.78 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.32 |
Crystal size (mm) | 0.20 × 0.16 × 0.14 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.655, 0.738 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4916, 2981, 2799 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.158, 1.09 |
No. of reflections | 2981 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.55, −1.79 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Sb1—S1 | 2.481 (1) | N2—C2 | 1.465 (8) |
Sb1—S2 | 2.555 (2) | N3—C5 | 1.330 (7) |
Sb1—Cl1 | 2.514 (1) | N3—C8 | 1.453 (9) |
Sb1—Cl2 | 2.670 (2) | N4—C5 | 1.306 (7) |
S1—C1 | 1.757 (5) | N4—C6 | 1.481 (9) |
S2—C5 | 1.745 (6) | C2—C3 | 1.492 (11) |
N1—C1 | 1.316 (7) | C3—C4 | 1.517 (11) |
N1—C4 | 1.462 (8) | C6—C7 | 1.461 (13) |
N2—C1 | 1.303 (7) | C7—C8 | 1.490 (12) |
S1—Sb1—Cl1 | 92.41 (5) | Cl1—Sb1—S2 | 92.43 (5) |
S1—Sb1—Cl2 | 76.62 (5) | Cl1—Sb1—Cl2 | 163.60 (6) |
S1—Sb1—S2 | 92.59 (5) | C1—S1—Sb1 | 104.01 (18) |
S2—Sb1—Cl2 | 76.18 (5) | C5—S2—Sb1 | 104.18 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl3i | 0.86 | 2.37 | 3.213 (6) | 169 |
N2—H2A···Cl3 | 0.86 | 2.44 | 3.227 (5) | 152 |
N3—H3A···Cl2ii | 0.86 | 2.40 | 3.203 (6) | 156 |
N4—H4A···Cl3i | 0.86 | 2.37 | 3.168 (6) | 155 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z. |
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Cyclic monothiones act exclusively as monodentate ligands with several metals. The complexes can be neutral molecules or cations. Some examples of cation complexes of the ligands are tetrakis[1-methyl-2(3H)-imidazolinethione]zinc(II) nitrate monohydrate (Nowell et al., 1979), tris(ethylenethiourea-S)tellurium(II) perchlorate and tris(trimethylenethiourea-S)tellurium(II) perchlorate (Foust, 1980). The ability of imidazolidine-2-thione (trimethylenethiourea) to reduce metallic salts and form complexes is demonstrated by the formation of tetrakis(imidazolidine-2-thione)copper(I) nitrate (Raper, 1985) and bis[bis(imidazolidine-2-thione)-µ-(imidazolidine-2-thione)copper(I)] diperchlorate (Raper et al., 1992) when reacted with copper(II) nitrate and copper(II) perchlorate, respectively. Our interest in the structures of antimony(III) halides complexed with S-donor ligands led us to investigate the title complex, (I).
The average thioamide N—C [1.314 (7) Å] and C—C [1.479 (12) Å] bond lengths of the ligands are shorter compared to the values in the free ligand (Dias & Truter, 1964) while the average S—C [1.751 (6) Å] and N—Cmethylene [1.456 (9) Å] bond lengths are longer. The longer S—C bond length results from the reduction in the π-electron density of the exocyclic S—C bond for the S atom coordinated to the metal atom. This reduction contributes to an increased π-electron density of the -thioamide N–C bonds, resulting in the shortening of the N—C bond lengths. The average S—C—N [119.2 (4)°], N—C—N [121.5 (5)°], C—N—C [122.7 (5)°] and N—C—C [109.9 (6)°] bond angles are also comparable with the reported values in the free ligand (Dias & Truter, 1964), while the average C—C—C bond angle is slightly bigger. Of the two Sb—Cl bonds, the Sb—Cl2 bond, where Cl2 is involved in intermolecular hydrogen bonding, is longer than Sb—Cl1. This behaviour is also observed in the Sb—Cl bond lengths reported by Razak et al. (1999) [SbCl3{[(C6H5)2PO]2CH2}] and in the Bi—Cl bond lengths reported in the structures of [BiCl3(pptu)3] and [{BiCl3(deimdt)2}2] [pptu is 1-phenyl-3-(2-pyridyl)-2-thiourea and deimdt is N,N'-diethylimidazolidine-2-thione; Battaglia et al., 1978].
The coordination around the Sb1 atom can be described as distorted octahedral. The basal plane is occupied by atoms S2, Cl1 and Cl2 from the cation and the Cl3- anion at a longer distance [Sb1···Cl3 = 3.010 (2) Å; S2—Sb1···Cl3 = 176.7 (1)°], which is less than the sum of the contact radii of Sb and Cl. The Sb1···Cl3 short contact has a lengthening effect on the Sb—S2 bond compared with that of Sb—S1. The apical positions of the octahedron are occupied by the S1 atom and the lone-pair electrons on Sb1.
The two trimethylenethiourea ring moieties adopt an envelope conformation, with atoms C3 and C7 deviating by 0.338 (9) and 0.262 (11) Å, respectively, from the mean plane through each of the two rings.
In the crystal, all the NH groups are involved in intermolecular hydrogen bonding (Table 2). N3—H3A···Cl2(1 - x, 1 - y,-z) hydrogen bonds interconnect molecules into dimers situated in the ab plane (Fig. 2). These dimers are arranged into infinite one-dimensional chains along the a axis as the Cl3 atoms form trifurcated intermolecular hydrogen bonds with the remaining NH groups; N2—H2A···Cl3, N1—H1A···Cl3(x - 1, y, z) and N4—H4A···Cl3(x - 1, y, z).