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Mol­ecules in the title crystal structure, C20H24O4, are linked into chains of R44(8) rings along [010] and these chains are linked into sheets via weak C—H...π(arene) inter­actions. These sheets are, in turn, linked via weak C—H...π(arene) and C—H...O inter­actions into a three-dimensional network. The ethyl substituent is disordered over two sites with refined occupancies of 0.700 (5) and 0.300 (5).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013894/lh2040sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013894/lh2040Isup2.hkl
Contains datablock I

CCDC reference: 608449

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.057
  • wR factor = 0.118
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT432_ALERT_2_A Short Inter X...Y Contact C13B .. C13B .. 2.51 Ang.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.33 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.76 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13A .. CG1 .. 3.24 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H13F .. CG1 .. 2.95 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H14B .. CG1 .. 2.95 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: ... This is a colaboration between people belonging to different institutions: - The synthesis and NMR ( 3 people ) - Diffraction ( 2 people ) - Writting of the paper (1 person)

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: SMART-NT (Bruker, 2001); cell refinement: SAINT-NT (Bruker, 2000); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-PC (Sheldrick, 1994); software used to prepare material for publication: PLATON (Spek, 2003) and Mercury (Bruno et al., 2002).

1-Ethyl-3-(4-hydroxy-3-methoxyphenyl)-6-methoxy-2-methylindan-5-ol top
Crystal data top
C20H24O4Z = 2
Mr = 328.39F(000) = 352
Triclinic, P1Dx = 1.211 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5124 (10) ÅCell parameters from 6723 reflections
b = 10.7915 (16) Åθ = 2.0–28.1°
c = 14.147 (2) ŵ = 0.08 mm1
α = 69.514 (2)°T = 298 K
β = 76.847 (3)°Needle, colorless
γ = 79.238 (3)°0.39 × 0.15 × 0.10 mm
V = 900.7 (2) Å3
Data collection top
Bruker SMART-NT CCD area-detector
diffractometer
Rint = 0.045
φ and ω scansθmax = 28.1°, θmin = 2.0°
6723 measured reflectionsh = 88
3926 independent reflectionsk = 1314
1834 reflections with I > 2σ(I)l = 1717
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 0.88 w = 1/[σ2(Fo2) + (0.0333P)2]
where P = (Fo2 + 2Fc2)/3
3926 reflections(Δ/σ)max < 0.001
230 parametersΔρmax = 0.19 e Å3
18 restraintsΔρmin = 0.16 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)
O10.3937 (3)1.08644 (16)0.31013 (14)0.0751 (8)
O20.0407 (2)0.97138 (14)0.36783 (12)0.0603 (7)
O30.1936 (3)0.31070 (17)0.51064 (13)0.0753 (8)
O40.0264 (2)0.20306 (15)0.42884 (12)0.0633 (7)
C10.5755 (5)1.1516 (3)0.2823 (3)0.135 (2)
C20.3992 (4)0.9831 (2)0.27496 (19)0.0501 (9)
C30.2102 (4)0.9251 (2)0.30602 (17)0.0470 (9)
C40.1906 (3)0.8196 (2)0.27752 (17)0.0470 (9)
C50.3608 (3)0.7706 (2)0.21675 (16)0.0405 (8)
C60.3757 (3)0.6582 (2)0.17493 (16)0.0447 (8)
C70.6188 (3)0.6248 (2)0.14741 (17)0.0463 (9)
C80.6805 (4)0.5488 (3)0.07072 (19)0.0712 (11)
C90.5676 (4)0.9339 (2)0.21480 (18)0.0521 (9)
C100.5486 (3)0.8264 (2)0.18617 (16)0.0425 (8)
C110.7100 (3)0.7582 (2)0.11956 (17)0.0490 (9)
C120.7373 (4)0.8434 (3)0.00601 (19)0.0732 (11)
C13A0.9397 (6)0.8166 (5)0.0608 (3)0.0905 (19)0.700 (5)
C140.3252 (5)0.3572 (3)0.5549 (2)0.1032 (16)
C150.1856 (4)0.3735 (2)0.40886 (18)0.0487 (9)
C160.0675 (3)0.3154 (2)0.3696 (2)0.0475 (9)
C170.0474 (4)0.3689 (2)0.2690 (2)0.0544 (10)
C180.1447 (3)0.4805 (2)0.20653 (19)0.0509 (9)
C190.2628 (3)0.5401 (2)0.24361 (17)0.0405 (8)
C200.2806 (4)0.4846 (2)0.34687 (18)0.0504 (9)
C13B0.8665 (16)0.9462 (11)0.0193 (7)0.098 (5)0.300 (5)
H1A0.688701.091600.313000.2030*
H1B0.545701.227600.305700.2030*
H20.070001.035800.378000.0900*
H40.000100.179800.487000.0950*
H4A0.064300.781300.298800.0560*
H60.318400.693900.111000.0540*
H70.667000.565800.210700.0560*
H8A0.637800.603900.006900.1070*
H1C0.616801.180200.209000.2030*
H8C0.831600.525200.059800.1070*
H90.693800.972400.193300.0630*
H110.847000.740200.142300.0590*
H12A0.622100.832000.022200.0880*0.700 (5)
H12B0.721200.936100.002200.0880*0.700 (5)
H13A0.943100.880800.128100.1360*0.700 (5)
H13B0.950500.728700.065100.1360*0.700 (5)
H13C1.056600.822800.032400.1360*0.700 (5)
H14A0.468600.351300.518700.1540*
H14B0.320500.303600.625600.1540*
H14C0.275800.448300.550600.1540*
H170.032000.330400.242200.0650*
H180.129700.515700.138000.0610*
H200.358200.523600.374200.0600*
H8B0.611000.469500.097000.1070*
H12C0.799500.786100.035400.0880*0.300 (5)
H12D0.598500.882700.011100.0880*0.300 (5)
H13D0.996700.909900.006400.1470*0.300 (5)
H13E0.793101.012800.010900.1470*0.300 (5)
H13F0.897400.985800.092500.1470*0.300 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0574 (12)0.0603 (12)0.1231 (17)0.0178 (9)0.0002 (11)0.0528 (12)
O20.0583 (11)0.0504 (11)0.0767 (13)0.0108 (8)0.0040 (10)0.0338 (10)
O30.1080 (15)0.0730 (13)0.0515 (12)0.0482 (11)0.0232 (11)0.0034 (10)
O40.0733 (12)0.0534 (11)0.0697 (12)0.0260 (9)0.0077 (9)0.0214 (10)
C10.069 (2)0.124 (3)0.263 (5)0.025 (2)0.007 (3)0.131 (3)
C20.0488 (16)0.0356 (14)0.0686 (18)0.0070 (12)0.0082 (14)0.0202 (13)
C30.0471 (15)0.0387 (15)0.0519 (16)0.0052 (12)0.0025 (13)0.0142 (12)
C40.0445 (15)0.0424 (15)0.0539 (16)0.0124 (12)0.0043 (12)0.0143 (13)
C50.0423 (14)0.0387 (14)0.0377 (14)0.0058 (11)0.0074 (11)0.0082 (11)
C60.0497 (15)0.0454 (15)0.0400 (14)0.0066 (12)0.0087 (12)0.0139 (12)
C70.0479 (15)0.0508 (15)0.0434 (15)0.0012 (12)0.0093 (12)0.0206 (12)
C80.0591 (17)0.091 (2)0.077 (2)0.0074 (15)0.0053 (15)0.0484 (18)
C90.0452 (15)0.0418 (15)0.0654 (18)0.0120 (12)0.0062 (13)0.0111 (14)
C100.0457 (14)0.0373 (14)0.0397 (14)0.0040 (12)0.0085 (11)0.0062 (11)
C110.0435 (14)0.0526 (16)0.0482 (16)0.0061 (12)0.0070 (12)0.0134 (13)
C120.0698 (19)0.078 (2)0.0560 (19)0.0098 (17)0.0032 (15)0.0104 (16)
C13A0.073 (3)0.100 (4)0.064 (3)0.004 (3)0.016 (2)0.009 (3)
C140.146 (3)0.112 (3)0.062 (2)0.067 (2)0.049 (2)0.0048 (18)
C150.0596 (16)0.0458 (15)0.0431 (16)0.0144 (13)0.0110 (13)0.0117 (13)
C160.0476 (15)0.0405 (15)0.0596 (18)0.0122 (12)0.0039 (13)0.0224 (14)
C170.0575 (17)0.0553 (17)0.0643 (19)0.0132 (13)0.0183 (14)0.0281 (15)
C180.0559 (16)0.0519 (16)0.0521 (16)0.0061 (13)0.0145 (13)0.0225 (14)
C190.0429 (14)0.0407 (14)0.0413 (14)0.0031 (11)0.0076 (11)0.0180 (12)
C200.0597 (16)0.0511 (16)0.0503 (16)0.0167 (13)0.0143 (13)0.0204 (13)
C13B0.109 (9)0.083 (9)0.074 (8)0.047 (7)0.002 (6)0.018 (6)
Geometric parameters (Å, º) top
O1—C11.399 (4)C19—C201.395 (3)
O1—C21.363 (3)C1—H1A0.9600
O2—C31.376 (3)C1—H1B0.9600
O3—C141.415 (4)C1—H1C0.9600
O3—C151.369 (3)C4—H4A0.9300
O4—C161.371 (3)C6—H60.9800
O2—H20.8200C7—H70.9800
O4—H40.8200C8—H8A0.9600
C2—C91.372 (4)C8—H8B0.9600
C2—C31.396 (4)C8—H8C0.9600
C3—C41.369 (3)C9—H90.9300
C4—C51.383 (3)C11—H110.9800
C5—C101.378 (3)C12—H12A0.9700
C5—C61.504 (3)C12—H12B0.9700
C6—C191.506 (3)C12—H12C0.9700
C6—C71.547 (3)C12—H12D0.9700
C7—C111.548 (3)C13A—H13A0.9600
C7—C81.521 (4)C13A—H13B0.9600
C9—C101.389 (3)C13A—H13C0.9600
C10—C111.510 (3)C13B—H13E0.9600
C11—C121.535 (3)C13B—H13F0.9600
C12—C13A1.482 (5)C13B—H13D0.9600
C12—C13B1.414 (12)C14—H14C0.9600
C15—C201.372 (3)C14—H14A0.9600
C15—C161.383 (3)C14—H14B0.9600
C16—C171.363 (4)C17—H170.9300
C17—C181.385 (3)C18—H180.9300
C18—C191.373 (3)C20—H200.9300
O1···O22.645 (2)H4···O32.2100
O1···O4i3.161 (2)H4···C3ii2.8600
O1···C16i3.163 (3)H4···H2iii2.4700
O1···C17i3.392 (3)H4···O2ii2.1300
O2···O12.645 (2)H4···H2ii2.4800
O2···O4i2.849 (2)H4A···O3ii2.7900
O2···O4ii2.825 (2)H4A···C192.9600
O3···O42.657 (2)H6···H8A2.5100
O4···O2iii2.849 (2)H6···H182.3500
O4···O32.657 (2)H7···C17viii3.0100
O4···O1iii3.161 (2)H7···C18viii3.0700
O4···O2ii2.825 (2)H7···C202.8700
O1···H22.1900H8A···H62.5100
O2···H4ii2.1300H8A···H12A2.3400
O2···H1Aiv2.5600H8A···C122.7700
O3···H4Aii2.7900H8A···C13A3.0600
O3···H42.2100H8A···H13B2.4700
O4···H2iii2.1100H8A···H12C2.2400
C4···C203.371 (3)H8B···C183.0800
C8···C13A3.360 (6)H8B···C192.8900
C9···C13B3.410 (10)H8C···H18viii2.4100
C13A···C83.360 (6)H8C···C18viii3.0900
C13B···C13Bv2.510 (16)H8C···H13B2.4200
C13B···C93.410 (10)H8C···H8Cix2.5500
C16···O1iii3.163 (3)H9···C12.5700
C17···O1iii3.392 (3)H9···H1A2.4500
C20···C43.371 (3)H9···H13E2.4100
C1···H92.5700H9···C13B3.0500
C3···H4ii2.8600H9···H1C2.2800
C3···H13Avi2.9000H11···H13D2.3100
C3···H13Fvi3.0400H11···H13C2.4800
C4···H203.1000H11···C18viii3.0700
C4···H13Fvi2.8200H12A···H8A2.3400
C5···H13Fvi3.0500H12A···C63.0500
C5···H202.8100H12A···C82.8600
C6···H12A3.0500H12B···C92.9400
C8···H12A2.8600H12C···C82.6300
C8···H13B2.7700H12C···H8A2.2400
C8···H12C2.6300H12D···H13Evi2.5900
C9···H13E2.8300H13A···C3vi2.9000
C9···H14Bvii2.8600H13B···H8A2.4700
C9···H12B2.9400H13B···C82.7700
C9···H1A2.8500H13B···H8C2.4200
C9···H1C2.7100H13C···H112.4800
C10···H14Bvii2.7900H13D···C13Bv2.0100
C10···H13E2.9400H13D···H13Dv1.9000
C12···H8A2.7700H13D···H13Fv2.2000
C13A···H8A3.0600H13D···H13Ev1.6600
C13B···H13Fv2.7800H13D···H112.3100
C13B···H13Ev2.3800H13E···C92.8300
C13B···H93.0500H13E···H12Dvi2.5900
C13B···H13Dv2.0100H13E···H13Dv1.6600
C14···H202.5500H13E···H13Fv2.5500
C15···H1Biii2.9600H13E···C102.9400
C16···H2iii2.9700H13E···H92.4100
C17···H7iv3.0100H13E···C13Bv2.3800
C18···H11iv3.0700H13F···C3vi3.0400
C18···H7iv3.0700H13F···C4vi2.8200
C18···H8B3.0800H13F···C5vi3.0500
C18···H8Civ3.0900H13F···H13Ev2.5500
C19···H8B2.8900H13F···C13Bv2.7800
C19···H4A2.9600H13F···H13Dv2.2000
C20···H72.8700H14A···C202.7800
C20···H14A2.7800H14A···H202.3800
C20···H14C2.7600H14B···C9vii2.8600
H1A···C92.8500H14B···C10vii2.7900
H1A···O2viii2.5600H14C···C202.7600
H1A···H92.4500H14C···H202.3000
H1B···C15i2.9600H18···H8Civ2.4100
H1C···H92.2800H18···H62.3500
H1C···C92.7100H20···C142.5500
H2···H4i2.4700H20···H14A2.3800
H2···H4ii2.4800H20···H14C2.3000
H2···O4i2.1100H20···C52.8100
H2···C16i2.9700H20···C43.1000
H2···O12.1900
C1—O1—C2118.0 (2)C7—C6—H6108.00
C14—O3—C15117.5 (2)C19—C6—H6108.00
C3—O2—H2109.00C6—C7—H7107.00
C16—O4—H4109.00C8—C7—H7107.00
O1—C2—C9126.7 (2)C11—C7—H7107.00
O1—C2—C3113.8 (2)C7—C8—H8A109.00
O3—C15—C20126.0 (2)C7—C8—H8B109.00
O3—C15—C16113.9 (2)C7—C8—H8C109.00
C3—C2—C9119.6 (2)H8A—C8—H8B109.00
C2—C3—C4120.9 (2)H8A—C8—H8C109.00
O2—C3—C2120.5 (2)H8B—C8—H8C110.00
O2—C3—C4118.6 (2)C2—C9—H9120.00
C3—C4—C5119.2 (2)C10—C9—H9120.00
C6—C5—C10110.84 (18)C7—C11—H11109.00
C4—C5—C6128.78 (19)C10—C11—H11109.00
C4—C5—C10120.4 (2)C12—C11—H11109.00
C5—C6—C19116.62 (18)C11—C12—H12A108.00
C5—C6—C7101.76 (17)C11—C12—H12B108.00
C7—C6—C19113.91 (18)C11—C12—H12C109.00
C6—C7—C11104.99 (17)C11—C12—H12D109.00
C6—C7—C8112.68 (19)C13A—C12—H12A108.00
C8—C7—C11118.24 (19)C13A—C12—H12B108.00
C2—C9—C10119.7 (2)H12A—C12—H12B107.00
C5—C10—C11111.05 (19)C13B—C12—H12C109.00
C5—C10—C9120.2 (2)C13B—C12—H12D109.00
C9—C10—C11128.7 (2)H12C—C12—H12D108.00
C7—C11—C12116.0 (2)C12—C13A—H13A110.00
C7—C11—C10101.30 (17)C12—C13A—H13B109.00
C10—C11—C12112.0 (2)C12—C13A—H13C109.00
C11—C12—C13A117.3 (3)H13A—C13A—H13B109.00
C11—C12—C13B113.5 (4)H13A—C13A—H13C110.00
C16—C15—C20120.1 (2)H13B—C13A—H13C109.00
O4—C16—C17118.9 (2)H13D—C13B—H13E109.00
O4—C16—C15121.6 (2)H13D—C13B—H13F109.00
C15—C16—C17119.5 (2)H13E—C13B—H13F109.00
C16—C17—C18120.3 (2)C12—C13B—H13E109.00
C17—C18—C19121.4 (2)C12—C13B—H13F109.00
C6—C19—C18121.5 (2)C12—C13B—H13D110.00
C6—C19—C20120.9 (2)H14A—C14—H14B109.00
C18—C19—C20117.6 (2)H14A—C14—H14C109.00
C15—C20—C19121.2 (2)O3—C14—H14A110.00
O1—C1—H1A109.00O3—C14—H14B109.00
O1—C1—H1B109.00O3—C14—H14C109.00
O1—C1—H1C109.00H14B—C14—H14C109.00
H1A—C1—H1B110.00C18—C17—H17120.00
H1A—C1—H1C109.00C16—C17—H17120.00
H1B—C1—H1C110.00C17—C18—H18119.00
C3—C4—H4A120.00C19—C18—H18119.00
C5—C4—H4A120.00C19—C20—H20119.00
C5—C6—H6108.00C15—C20—H20119.00
C1—O1—C2—C3179.5 (2)C7—C6—C19—C2072.5 (3)
C1—O1—C2—C90.7 (4)C19—C6—C7—C873.6 (2)
C14—O3—C15—C16175.0 (2)C6—C7—C11—C1030.2 (2)
C14—O3—C15—C205.4 (4)C8—C7—C11—C1235.3 (3)
O1—C2—C3—C4179.6 (2)C8—C7—C11—C10156.8 (2)
O1—C2—C9—C10179.3 (2)C6—C7—C11—C1291.4 (2)
C9—C2—C3—O2178.9 (2)C2—C9—C10—C50.9 (3)
C9—C2—C3—C40.2 (4)C2—C9—C10—C11178.8 (2)
O1—C2—C3—O20.9 (3)C5—C10—C11—C719.4 (2)
C3—C2—C9—C100.5 (4)C5—C10—C11—C12104.9 (2)
C2—C3—C4—C50.3 (3)C9—C10—C11—C7162.5 (2)
O2—C3—C4—C5179.0 (2)C9—C10—C11—C1273.2 (3)
C3—C4—C5—C6179.0 (2)C10—C11—C12—C13A157.0 (3)
C3—C4—C5—C100.7 (3)C7—C11—C12—C13A87.4 (3)
C4—C5—C6—C1937.0 (3)O3—C15—C16—C17180.0 (2)
C4—C5—C6—C7161.5 (2)O3—C15—C16—O41.6 (3)
C4—C5—C10—C11179.26 (19)O3—C15—C20—C19179.7 (2)
C6—C5—C10—C9178.7 (2)C20—C15—C16—O4178.8 (2)
C6—C5—C10—C110.5 (2)C20—C15—C16—C170.4 (4)
C10—C5—C6—C19143.32 (19)C16—C15—C20—C190.8 (4)
C4—C5—C10—C91.0 (3)C15—C16—C17—C180.1 (4)
C10—C5—C6—C718.7 (2)O4—C16—C17—C18178.4 (2)
C5—C6—C7—C8160.05 (19)C16—C17—C18—C190.1 (4)
C5—C6—C7—C1130.1 (2)C17—C18—C19—C6177.6 (2)
C19—C6—C7—C11156.42 (18)C17—C18—C19—C200.3 (3)
C5—C6—C19—C18136.5 (2)C6—C19—C20—C15177.2 (2)
C5—C6—C19—C2045.6 (3)C18—C19—C20—C150.8 (3)
C7—C6—C19—C18105.3 (2)
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z+1; (iii) x, y1, z; (iv) x1, y, z; (v) x+2, y+2, z; (vi) x+1, y+2, z; (vii) x+1, y+1, z+1; (viii) x+1, y, z; (ix) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.822.192.645 (2)115
O2—H2···O4i0.822.112.849 (2)150
O4—H4···O30.822.212.657 (2)114
O4—H4···O2ii0.822.132.825 (2)143
C1—H1A···O2viii0.962.563.499 (4)167
C13A—H13A···Cg1vi0.963.243.999 (5)137
C13B—H13F···Cg1vi0.962.953.663 (10)132
C14—H14B···Cg1vii0.962.953.697 (3)137
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z+1; (vi) x+1, y+2, z; (vii) x+1, y+1, z+1; (viii) x+1, y, z.
 

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