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In the title compound, C17H22ClN3O2, the aromatic fused ring system and the amide group are close to being coplanar [dihedral angle = 14.66 (16)°]. Thus, the amide NH group is sterically blocked from forming a hydrogen bond by the pendant ethyl substituent of the adjacent five-membered ring. The NH group of the five-membered ring makes an inter­molecular N—H...O bond, resulting in centrosymmetric dimers of mol­ecules containing R22(10) loops.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031285/tk2171sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031285/tk2171Isup2.hkl
Contains datablock I

CCDC reference: 657676

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.129
  • wR factor = 0.289
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.159 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.16 PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 12
Alert level C RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.129 RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.289 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT082_ALERT_2_C High R1 Value .................................. 0.13 PLAT084_ALERT_2_C High R2 Value .................................. 0.29 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT414_ALERT_2_C Short Intra D-H..H-X H2 .. H9A .. 1.91 Ang.
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As part of our on-going investigations of allosteric modulators of the cannabinoid CB1 receptor (Price et al., 2005), the title compound, (I), C17H22ClN3O2, has been synthesized and structurally characterized (Fig. 1). It complements C18H24ClN3O2, reported in the next paper (Muirhead, Trembleau & Harrison, 2007).

The dihedral angle between the mean planes of the C1—C8/N1 fused aromatic ring system and atoms C6/C7/N1/O2 in (I) is 14.66 (16)°, i.e. the two fragments are slightly twisted. Atom C10 is displaced from the C1—C8/N1 mean plane by 1.459 (14) Å. The C14—C17/N3/O2 ring in (I) has a typical chair conformation, with N3 and O2 displaced from the mean plane of the carbon atoms by -0.656 (12)Å and 0.635 (14) Å, respectively. Otherwise, the bond lengths and angles in (I) may be regarded as normal (Allen et al., 1995).

The crystal packing for (I) results in inversion dimers linked by N1—H1···O1i hydrogen bonds (Table 1), thus forming R22(10) loops (Bernstein et al., 1995). The amide N2—H2 group is sterically blocked by the C9/C10 ethyl substituent to the 5-membered ring from making an hydrogen bond. A short C—H···O interaction also occurs (Table 1).

Related literature top

For a related structure, see: Muirhead et al. (2007). For background, see: Price et al. (2005); Allen et al. (1995); Bernstein et al. (1995). For related literature, see: Muirhead & Trembleau (2007).

Experimental top

To a solution of pentafluorophenol (0.130 g, 0.706 mmol) in dichloromethane (5 ml), 3-ethylindole-2-carboxylic acid (0.100 g, 0.447 mmol) (Muirhead & Trembleau, 2007) and N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.111 g, 0.581 mmol) were added and stirred at room temperature for 80 min. Silica gel (1.2 g) was added to the reaction mixture, stirred for 5 min and the mixture filtered through Celite and the solvent removed to give the activated ester as a white solid (0.167 g). The ester was redissolved in dichloromethane (2.6 ml), to which was added 2-morpholinoethylamine 5 (0.068 ml, 0.514 mmol) and triethylamine (0.072 ml, 0.514 mmol) and stirred at room temperature for 80 min. The solvent was removed under vacuum and the resulting solid taken up into ethyl acetate (30 ml), washed with saturated potassium carbonate solution (5 ml), dried over magnesium sulfate, filtered and dried. Recrystallization of the crude material from hot ethanol afforded 0.066 g (44%) of colourless blocks of (I)

Refinement top

The H atoms were placed in idealized locations (C—H = 0.93–0.99 Å, N—H = 0.88 Å) and refined as riding with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(methyl C).

Structure description top

As part of our on-going investigations of allosteric modulators of the cannabinoid CB1 receptor (Price et al., 2005), the title compound, (I), C17H22ClN3O2, has been synthesized and structurally characterized (Fig. 1). It complements C18H24ClN3O2, reported in the next paper (Muirhead, Trembleau & Harrison, 2007).

The dihedral angle between the mean planes of the C1—C8/N1 fused aromatic ring system and atoms C6/C7/N1/O2 in (I) is 14.66 (16)°, i.e. the two fragments are slightly twisted. Atom C10 is displaced from the C1—C8/N1 mean plane by 1.459 (14) Å. The C14—C17/N3/O2 ring in (I) has a typical chair conformation, with N3 and O2 displaced from the mean plane of the carbon atoms by -0.656 (12)Å and 0.635 (14) Å, respectively. Otherwise, the bond lengths and angles in (I) may be regarded as normal (Allen et al., 1995).

The crystal packing for (I) results in inversion dimers linked by N1—H1···O1i hydrogen bonds (Table 1), thus forming R22(10) loops (Bernstein et al., 1995). The amide N2—H2 group is sterically blocked by the C9/C10 ethyl substituent to the 5-membered ring from making an hydrogen bond. A short C—H···O interaction also occurs (Table 1).

For a related structure, see: Muirhead et al. (2007). For background, see: Price et al. (2005); Allen et al. (1995); Bernstein et al. (1995). For related literature, see: Muirhead & Trembleau (2007).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) showing 40% displacement ellipsoids.
[Figure 2] Fig. 2. An inversion dimer in the crystal of (I) with hydrogen bonds shown as double dashed lines. All carbon-bound H atoms are omitted for clarity. Symmetry code as in Table 1.
5-Chloro-3-ethyl-N-(2-morpholin-4-ylethyl)-1H-indole-2-carboxamide top
Crystal data top
C17H22ClN3O2Z = 2
Mr = 335.83F(000) = 356
Triclinic, P1Dx = 1.296 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.1886 (13) ÅCell parameters from 3029 reflections
b = 9.7175 (13) Åθ = 2.9–27.5°
c = 11.2807 (10) ŵ = 0.24 mm1
α = 73.755 (6)°T = 120 K
β = 79.612 (6)°Block, colourles
γ = 63.056 (5)°0.12 × 0.08 × 0.06 mm
V = 860.38 (18) Å3
Data collection top
Nonius KappaCCD
diffractometer
3155 independent reflections
Radiation source: fine-focus sealed tube1516 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.159
ω and φ scansθmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 1111
Tmin = 0.972, Tmax = 0.987k = 1111
10924 measured reflectionsl = 1313
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)] = 0.129Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.289H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.039P)2 + 4.7894P]
where P = (Fo2 + 2Fc2)/3
3155 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C17H22ClN3O2γ = 63.056 (5)°
Mr = 335.83V = 860.38 (18) Å3
Triclinic, P1Z = 2
a = 9.1886 (13) ÅMo Kα radiation
b = 9.7175 (13) ŵ = 0.24 mm1
c = 11.2807 (10) ÅT = 120 K
α = 73.755 (6)°0.12 × 0.08 × 0.06 mm
β = 79.612 (6)°
Data collection top
Nonius KappaCCD
diffractometer
3155 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
1516 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.987Rint = 0.159
10924 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.1290 restraints
wR(F2) = 0.289H-atom parameters constrained
S = 1.07Δρmax = 0.36 e Å3
3155 reflectionsΔρmin = 0.38 e Å3
208 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
C10.9563 (9)0.2441 (9)0.5535 (6)0.0404 (19)
C21.0584 (10)0.1514 (9)0.4714 (7)0.046 (2)
H2A1.12220.04140.50160.055*
C31.0679 (9)0.2169 (9)0.3478 (7)0.0393 (18)
H31.13650.15470.29080.047*
C40.9723 (9)0.3796 (8)0.3089 (6)0.0353 (18)
C50.8706 (9)0.4732 (9)0.3911 (7)0.0356 (17)
C60.8631 (9)0.4013 (9)0.5165 (6)0.0399 (19)
H60.79410.46160.57460.048*
C70.8504 (9)0.6271 (8)0.1992 (6)0.0364 (18)
C80.7926 (9)0.6324 (8)0.3215 (6)0.0368 (18)
C90.6664 (10)0.7674 (9)0.3750 (7)0.050 (2)
H9A0.68600.86300.33710.060*
H9B0.67930.74170.46490.060*
C100.4926 (12)0.8046 (14)0.3552 (10)0.089 (4)
H10A0.41630.89330.39250.134*
H10B0.47130.71130.39390.134*
H10C0.47770.83340.26630.134*
C110.8181 (9)0.7478 (9)0.0822 (7)0.0399 (19)
C120.7132 (13)1.0292 (9)0.0191 (7)0.061 (3)
H12A0.59911.07110.04170.073*
H12B0.78750.99270.09030.073*
C130.7398 (12)1.1575 (10)0.0105 (7)0.057 (2)
H13A0.85841.12290.01430.069*
H13B0.69931.25420.05650.069*
C140.4797 (11)1.2850 (12)0.1173 (8)0.063 (3)
H14A0.43561.22230.09200.075*
H14B0.45691.38430.05300.075*
C150.3973 (12)1.3236 (14)0.2387 (10)0.086 (4)
H15A0.27851.38750.22890.103*
H15B0.41211.22380.30040.103*
C160.6288 (13)1.3189 (14)0.2949 (10)0.080 (3)
H16A0.65011.21820.35710.096*
H16B0.67211.37930.32430.096*
C170.7163 (10)1.2833 (11)0.1741 (8)0.060 (2)
H17A0.70021.38380.11290.072*
H17B0.83501.22110.18510.072*
N10.9593 (7)0.4741 (7)0.1933 (5)0.0373 (15)
H11.01190.44270.12560.045*
N20.7448 (9)0.8985 (7)0.0874 (5)0.053 (2)
H20.71300.92070.16090.064*
N30.6561 (8)1.1948 (7)0.1276 (6)0.0426 (16)
O10.8611 (7)0.7085 (6)0.0193 (5)0.0570 (16)
O20.4578 (8)1.4077 (9)0.2841 (7)0.086 (2)
Cl10.9493 (3)0.1505 (3)0.71052 (19)0.0626 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.038 (5)0.045 (5)0.034 (4)0.022 (4)0.005 (4)0.005 (4)
C20.039 (5)0.039 (5)0.047 (5)0.008 (4)0.003 (4)0.006 (4)
C30.034 (4)0.042 (5)0.039 (4)0.014 (4)0.001 (3)0.013 (4)
C40.031 (4)0.036 (4)0.041 (4)0.018 (4)0.003 (3)0.009 (4)
C50.031 (4)0.038 (4)0.043 (4)0.017 (4)0.000 (4)0.015 (4)
C60.041 (5)0.046 (5)0.031 (4)0.020 (4)0.008 (3)0.011 (4)
C70.040 (5)0.033 (4)0.035 (4)0.014 (4)0.004 (3)0.007 (3)
C80.037 (4)0.035 (4)0.040 (4)0.014 (4)0.004 (4)0.017 (4)
C90.061 (6)0.044 (5)0.037 (4)0.019 (4)0.002 (4)0.008 (4)
C100.052 (7)0.104 (9)0.083 (8)0.007 (6)0.008 (6)0.033 (7)
C110.042 (5)0.037 (5)0.039 (4)0.014 (4)0.003 (4)0.010 (4)
C120.103 (8)0.037 (5)0.034 (4)0.025 (5)0.003 (5)0.003 (4)
C130.072 (7)0.042 (5)0.047 (5)0.019 (5)0.008 (5)0.008 (4)
C140.063 (7)0.074 (7)0.063 (6)0.040 (6)0.001 (5)0.017 (5)
C150.047 (6)0.115 (9)0.112 (9)0.034 (6)0.018 (6)0.066 (8)
C160.070 (8)0.105 (9)0.099 (8)0.044 (7)0.005 (6)0.069 (7)
C170.040 (5)0.059 (6)0.077 (6)0.012 (5)0.001 (5)0.029 (5)
N10.044 (4)0.035 (4)0.029 (3)0.012 (3)0.003 (3)0.014 (3)
N20.089 (6)0.032 (4)0.026 (3)0.015 (4)0.000 (3)0.009 (3)
N30.038 (4)0.045 (4)0.048 (4)0.015 (3)0.000 (3)0.021 (3)
O10.071 (4)0.048 (3)0.035 (3)0.008 (3)0.001 (3)0.018 (3)
O20.049 (4)0.105 (6)0.129 (6)0.031 (4)0.018 (4)0.080 (5)
Cl10.0756 (17)0.0625 (15)0.0402 (12)0.0305 (13)0.0032 (11)0.0040 (10)
Geometric parameters (Å, º) top
C1—C61.352 (10)C12—N21.442 (9)
C1—C21.393 (10)C12—C131.505 (11)
C1—Cl11.754 (7)C12—H12A0.9900
C2—C31.366 (10)C12—H12B0.9900
C2—H2A0.9500C13—N31.455 (9)
C3—C41.399 (10)C13—H13A0.9900
C3—H30.9500C13—H13B0.9900
C4—N11.357 (9)C14—N31.460 (11)
C4—C51.397 (9)C14—C151.499 (12)
C5—C61.397 (10)C14—H14A0.9900
C5—C81.429 (10)C14—H14B0.9900
C6—H60.9500C15—O21.410 (11)
C7—N11.378 (9)C15—H15A0.9900
C7—C81.393 (9)C15—H15B0.9900
C7—C111.472 (10)C16—O21.418 (11)
C8—C91.497 (10)C16—C171.497 (12)
C9—C101.514 (12)C16—H16A0.9900
C9—H9A0.9900C16—H16B0.9900
C9—H9B0.9900C17—N31.452 (10)
C10—H10A0.9800C17—H17A0.9900
C10—H10B0.9800C17—H17B0.9900
C10—H10C0.9800N1—H10.8800
C11—O11.248 (8)N2—H20.8800
C11—N21.319 (9)
C6—C1—C2122.5 (7)C13—C12—H12B109.8
C6—C1—Cl1119.6 (6)H12A—C12—H12B108.3
C2—C1—Cl1117.9 (6)N3—C13—C12111.9 (7)
C3—C2—C1120.7 (7)N3—C13—H13A109.2
C3—C2—H2A119.7C12—C13—H13A109.2
C1—C2—H2A119.7N3—C13—H13B109.2
C2—C3—C4117.1 (7)C12—C13—H13B109.2
C2—C3—H3121.4H13A—C13—H13B107.9
C4—C3—H3121.4N3—C14—C15110.3 (8)
N1—C4—C5108.2 (6)N3—C14—H14A109.6
N1—C4—C3129.4 (7)C15—C14—H14A109.6
C5—C4—C3122.3 (7)N3—C14—H14B109.6
C4—C5—C6118.7 (7)C15—C14—H14B109.6
C4—C5—C8107.9 (6)H14A—C14—H14B108.1
C6—C5—C8133.4 (7)O2—C15—C14113.3 (8)
C1—C6—C5118.6 (7)O2—C15—H15A108.9
C1—C6—H6120.7C14—C15—H15A108.9
C5—C6—H6120.7O2—C15—H15B108.9
N1—C7—C8109.4 (6)C14—C15—H15B108.9
N1—C7—C11117.3 (6)H15A—C15—H15B107.7
C8—C7—C11133.3 (7)O2—C16—C17111.7 (8)
C7—C8—C5105.4 (6)O2—C16—H16A109.3
C7—C8—C9130.1 (7)C17—C16—H16A109.3
C5—C8—C9124.3 (6)O2—C16—H16B109.3
C8—C9—C10113.5 (7)C17—C16—H16B109.3
C8—C9—H9A108.9H16A—C16—H16B107.9
C10—C9—H9A108.9N3—C17—C16111.0 (7)
C8—C9—H9B108.9N3—C17—H17A109.4
C10—C9—H9B108.9C16—C17—H17A109.4
H9A—C9—H9B107.7N3—C17—H17B109.4
C9—C10—H10A109.5C16—C17—H17B109.4
C9—C10—H10B109.5H17A—C17—H17B108.0
H10A—C10—H10B109.5C4—N1—C7109.1 (6)
C9—C10—H10C109.5C4—N1—H1125.5
H10A—C10—H10C109.5C7—N1—H1125.5
H10B—C10—H10C109.5C11—N2—C12124.4 (6)
O1—C11—N2120.9 (7)C11—N2—H2117.8
O1—C11—C7120.8 (7)C12—N2—H2117.8
N2—C11—C7118.3 (6)C17—N3—C13112.2 (6)
N2—C12—C13109.3 (7)C17—N3—C14108.7 (6)
N2—C12—H12A109.8C13—N3—C14111.6 (7)
C13—C12—H12A109.8C15—O2—C16109.2 (7)
N2—C12—H12B109.8
C6—C1—C2—C30.3 (12)N1—C7—C11—O114.0 (11)
Cl1—C1—C2—C3179.3 (6)C8—C7—C11—O1166.0 (8)
C1—C2—C3—C40.5 (11)N1—C7—C11—N2165.1 (7)
C2—C3—C4—N1179.5 (7)C8—C7—C11—N214.9 (13)
C2—C3—C4—C50.1 (11)N2—C12—C13—N348.9 (10)
N1—C4—C5—C6179.8 (6)N3—C14—C15—O256.9 (12)
C3—C4—C5—C60.6 (11)O2—C16—C17—N358.9 (11)
N1—C4—C5—C80.2 (8)C5—C4—N1—C70.3 (8)
C3—C4—C5—C8179.4 (7)C3—C4—N1—C7179.8 (7)
C2—C1—C6—C50.3 (12)C8—C7—N1—C40.6 (8)
Cl1—C1—C6—C5179.9 (6)C11—C7—N1—C4179.4 (6)
C4—C5—C6—C10.8 (11)O1—C11—N2—C122.5 (13)
C8—C5—C6—C1179.2 (8)C7—C11—N2—C12176.6 (8)
N1—C7—C8—C50.7 (8)C13—C12—N2—C11141.5 (8)
C11—C7—C8—C5179.3 (8)C16—C17—N3—C13179.6 (8)
N1—C7—C8—C9176.1 (7)C16—C17—N3—C1456.5 (10)
C11—C7—C8—C93.9 (14)C12—C13—N3—C17163.8 (7)
C4—C5—C8—C70.6 (8)C12—C13—N3—C1474.0 (9)
C6—C5—C8—C7179.5 (8)C15—C14—N3—C1754.9 (10)
C4—C5—C8—C9176.3 (7)C15—C14—N3—C13179.1 (7)
C6—C5—C8—C93.7 (13)C14—C15—O2—C1656.9 (12)
C7—C8—C9—C1076.4 (11)C17—C16—O2—C1557.2 (11)
C5—C8—C9—C1098.2 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.881.972.803 (7)157
C6—H6···O2ii0.952.583.491 (11)161
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC17H22ClN3O2
Mr335.83
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)9.1886 (13), 9.7175 (13), 11.2807 (10)
α, β, γ (°)73.755 (6), 79.612 (6), 63.056 (5)
V3)860.38 (18)
Z2
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.12 × 0.08 × 0.06
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.972, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
10924, 3155, 1516
Rint0.159
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.129, 0.289, 1.07
No. of reflections3155
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.36, 0.38

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.881.972.803 (7)157
C6—H6···O2ii0.952.583.491 (11)161
Symmetry codes: (i) x+2, y+1, z; (ii) x+1, y+2, z+1.
 

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