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The drug norfloxacin and ligand 2,2'-bipyridine coordinate to copper(II) yielding a mixed-ligand complex, [Cu(C16H18FN3O3)(NO3)(C10H8N2)](NO3)·2H2O or [Cu(H-Norf)(NO3)(bpy)](NO3)·2H2O. The CuII atom has a five-coordinate environment with square-based pyramidal geometry, which involves two N atoms from the 2,2'-bipyridine ligand, two O atoms from the norfloxacinate ligand and one nitrate O atom. Weak interactions between O and Cu result in a centrosymmetric dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031861/dn6179sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031861/dn6179Isup2.hkl
Contains datablock I

CCDC reference: 262241

Key indicators

  • Single-crystal X-ray study
  • T = 130 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.080
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent O Ueq(max)/Ueq(min) ... 4.07 Ratio
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.03 PLAT213_ALERT_2_C Atom O6 has ADP max/min Ratio ............. 3.10 prolat PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - N6 .. 6.28 su PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - N6 .. 6.31 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Cu - O4 .. 5.70 su PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O8 .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. N7 .. 2.70 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(2,2'-bipyridine)[1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-4-ium- 1-yl)quinoline-3-carboxylato]nitratocopper(II) nitrate dihydrate top
Crystal data top
[Cu(C16H18FN3O3)(NO3)(C10H8N2)](NO3)·2H2OF(000) = 1444
Mr = 699.12Dx = 1.668 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6954 reflections
a = 13.9080 (8) Åθ = 1.5–25.0°
b = 13.8441 (8) ŵ = 0.87 mm1
c = 14.4835 (9) ÅT = 130 K
β = 93.173 (3)°Prism, blue
V = 2784.4 (3) Å30.32 × 0.20 × 0.15 mm
Z = 4
Data collection top
Rigaku Mercury CCD
diffractometer
4902 independent reflections
Radiation source: RX4561 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1615
Tmin = 0.770, Tmax = 0.852k = 1616
17478 measured reflectionsl = 1617
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0385P)2 + 2.0954P]
where P = (Fo2 + 2Fc2)/3
4902 reflections(Δ/σ)max = 0.001
428 parametersΔρmax = 0.44 e Å3
6 restraintsΔρmin = 0.29 e Å3
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
Cu0.562304 (17)0.619036 (18)0.478556 (17)0.01392 (9)
O10.62037 (10)0.53634 (11)0.22056 (10)0.0183 (3)
O20.61922 (10)0.57102 (10)0.36969 (10)0.0170 (3)
O30.43599 (10)0.57074 (10)0.44121 (10)0.0161 (3)
O40.52470 (12)0.76620 (11)0.40022 (12)0.0280 (4)
O50.45063 (15)0.87282 (15)0.48047 (15)0.0457 (5)
O60.60499 (15)0.87512 (15)0.4789 (2)0.0655 (8)
O70.58529 (15)0.70766 (15)0.00621 (16)0.0507 (6)
O80.71344 (12)0.75584 (14)0.07310 (14)0.0371 (5)
O90.57868 (13)0.74306 (14)0.13846 (15)0.0416 (5)
O100.69350 (13)0.78801 (15)0.30013 (15)0.0400 (5)
H30.652 (2)0.782 (2)0.3414 (16)0.060*
H40.672 (2)0.763 (2)0.2495 (14)0.060*
O110.22285 (15)0.30834 (17)0.10471 (13)0.0441 (5)
H10.1639 (13)0.315 (3)0.088 (2)0.066*
H20.253 (2)0.293 (3)0.0567 (18)0.066*
F0.08296 (8)0.56467 (10)0.45241 (9)0.0228 (3)
N10.52094 (12)0.65893 (12)0.60288 (12)0.0150 (4)
N20.68982 (12)0.66130 (12)0.53459 (12)0.0147 (4)
N30.33287 (12)0.55211 (12)0.17020 (12)0.0134 (4)
N40.00350 (12)0.54694 (12)0.27594 (12)0.0144 (4)
N50.19135 (12)0.49231 (13)0.22420 (13)0.0170 (4)
H5A0.25460.50560.22590.020*
H5B0.18530.43720.19210.020*
N60.52750 (16)0.83850 (15)0.45415 (15)0.0310 (5)
N70.62535 (14)0.73499 (14)0.06818 (17)0.0305 (5)
C0.57650 (14)0.55691 (14)0.29068 (15)0.0140 (4)
C10.43070 (15)0.66242 (15)0.62983 (15)0.0174 (4)
H1A0.38020.65120.58630.021*
C20.40970 (15)0.68210 (15)0.72017 (16)0.0200 (5)
H2A0.34620.68470.73710.024*
C30.48510 (16)0.69787 (16)0.78483 (16)0.0210 (5)
H3A0.47280.70960.84630.025*
C40.57916 (16)0.69613 (15)0.75753 (16)0.0197 (5)
H4A0.63060.70700.80010.024*
C50.59483 (14)0.67778 (14)0.66552 (15)0.0154 (4)
C60.69033 (14)0.67995 (14)0.62599 (15)0.0152 (4)
C70.77532 (15)0.70300 (15)0.67701 (16)0.0181 (5)
H70.77540.71360.74040.022*
C80.85931 (15)0.70970 (15)0.63089 (17)0.0212 (5)
H80.91690.72490.66330.025*
C90.85797 (15)0.69385 (15)0.53655 (16)0.0211 (5)
H90.91400.69940.50470.025*
C100.77136 (15)0.66953 (15)0.49036 (16)0.0178 (5)
H100.76990.65860.42690.021*
C110.40758 (14)0.56619 (14)0.35561 (14)0.0127 (4)
C120.46850 (14)0.56168 (14)0.28045 (14)0.0135 (4)
C130.42764 (14)0.55474 (14)0.19178 (15)0.0136 (4)
H130.46890.55170.14350.016*
C140.29396 (15)0.54690 (17)0.07233 (15)0.0192 (5)
H14A0.25450.60350.05920.023*
H14B0.25260.49070.06540.023*
C150.36985 (16)0.54099 (18)0.00173 (16)0.0245 (5)
H15A0.41200.59580.00850.037*
H15B0.33930.54080.05940.037*
H15C0.40650.48270.01120.037*
C160.26802 (14)0.55496 (14)0.24086 (15)0.0132 (4)
C170.16791 (14)0.55027 (14)0.22062 (15)0.0146 (4)
H170.14430.54670.15940.018*
C180.10407 (14)0.55093 (14)0.29101 (15)0.0140 (4)
C190.14420 (14)0.55912 (15)0.38257 (15)0.0156 (4)
C200.23995 (14)0.56389 (14)0.40378 (15)0.0145 (4)
H200.26280.56890.46520.017*
C210.30505 (14)0.56131 (14)0.33281 (14)0.0136 (4)
C220.03389 (14)0.55877 (16)0.18016 (15)0.0180 (5)
H22A0.01800.50220.14450.022*
H22B0.00390.61450.15300.022*
C230.14260 (15)0.57235 (16)0.17615 (16)0.0206 (5)
H23A0.15780.63330.20490.025*
H23B0.16670.57480.11210.025*
C240.14969 (14)0.47853 (16)0.32014 (15)0.0193 (5)
H24A0.17930.42300.34800.023*
H24B0.16260.53500.35710.023*
C250.04228 (14)0.46305 (15)0.31838 (15)0.0175 (5)
H25A0.01520.45410.38100.021*
H25B0.02950.40520.28330.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu0.00881 (14)0.01823 (15)0.01447 (15)0.00076 (9)0.00171 (10)0.00140 (10)
O10.0107 (7)0.0280 (8)0.0164 (8)0.0018 (6)0.0013 (6)0.0020 (6)
O20.0104 (7)0.0242 (8)0.0163 (8)0.0008 (6)0.0008 (6)0.0029 (6)
O30.0113 (7)0.0226 (8)0.0142 (8)0.0025 (6)0.0010 (6)0.0005 (6)
O40.0365 (10)0.0202 (8)0.0265 (10)0.0017 (7)0.0055 (7)0.0019 (7)
O50.0428 (12)0.0521 (13)0.0425 (12)0.0001 (10)0.0063 (9)0.0209 (10)
O60.0395 (12)0.0416 (12)0.110 (2)0.0047 (9)0.0451 (13)0.0234 (12)
O70.0402 (11)0.0486 (12)0.0611 (15)0.0008 (9)0.0181 (10)0.0166 (11)
O80.0169 (9)0.0499 (11)0.0444 (12)0.0032 (8)0.0008 (8)0.0048 (9)
O90.0242 (10)0.0387 (11)0.0631 (14)0.0042 (8)0.0141 (9)0.0007 (10)
O100.0277 (10)0.0478 (12)0.0443 (12)0.0063 (8)0.0004 (9)0.0242 (10)
O110.0400 (12)0.0631 (14)0.0285 (11)0.0060 (10)0.0030 (9)0.0052 (10)
F0.0129 (6)0.0399 (8)0.0159 (7)0.0028 (5)0.0040 (5)0.0045 (6)
N10.0135 (9)0.0135 (8)0.0178 (10)0.0000 (7)0.0002 (7)0.0007 (7)
N20.0118 (9)0.0137 (8)0.0184 (10)0.0000 (7)0.0017 (7)0.0005 (7)
N30.0100 (8)0.0160 (9)0.0140 (9)0.0003 (6)0.0006 (7)0.0005 (7)
N40.0096 (8)0.0174 (9)0.0161 (9)0.0012 (7)0.0003 (7)0.0016 (7)
N50.0064 (8)0.0191 (9)0.0254 (10)0.0003 (7)0.0003 (7)0.0011 (8)
N60.0383 (13)0.0243 (11)0.0287 (12)0.0009 (9)0.0141 (10)0.0043 (9)
N70.0225 (11)0.0225 (10)0.0465 (14)0.0053 (8)0.0008 (10)0.0004 (10)
C0.0115 (10)0.0129 (10)0.0173 (11)0.0012 (7)0.0018 (8)0.0002 (8)
C10.0136 (10)0.0152 (10)0.0232 (12)0.0014 (8)0.0016 (9)0.0004 (9)
C20.0150 (11)0.0172 (11)0.0283 (13)0.0002 (8)0.0041 (9)0.0022 (9)
C30.0265 (12)0.0198 (11)0.0169 (12)0.0010 (9)0.0041 (9)0.0025 (9)
C40.0195 (11)0.0192 (11)0.0198 (12)0.0003 (8)0.0033 (9)0.0036 (9)
C50.0144 (10)0.0107 (10)0.0207 (12)0.0000 (8)0.0026 (8)0.0006 (8)
C60.0152 (10)0.0107 (10)0.0191 (12)0.0013 (8)0.0035 (8)0.0008 (8)
C70.0178 (11)0.0171 (10)0.0187 (12)0.0009 (8)0.0052 (9)0.0023 (9)
C80.0132 (11)0.0173 (11)0.0322 (14)0.0004 (8)0.0066 (9)0.0008 (10)
C90.0138 (11)0.0201 (11)0.0294 (13)0.0000 (8)0.0007 (9)0.0029 (9)
C100.0148 (11)0.0175 (11)0.0212 (12)0.0013 (8)0.0007 (9)0.0001 (9)
C110.0133 (10)0.0103 (9)0.0142 (11)0.0009 (7)0.0024 (8)0.0010 (8)
C120.0093 (10)0.0135 (10)0.0177 (11)0.0003 (7)0.0004 (8)0.0011 (8)
C130.0108 (10)0.0145 (10)0.0159 (11)0.0008 (8)0.0029 (8)0.0002 (8)
C140.0146 (11)0.0284 (12)0.0142 (11)0.0005 (9)0.0023 (8)0.0017 (9)
C150.0159 (11)0.0418 (14)0.0156 (12)0.0006 (10)0.0006 (9)0.0040 (10)
C160.0114 (10)0.0124 (10)0.0156 (11)0.0010 (7)0.0006 (8)0.0007 (8)
C170.0133 (10)0.0161 (10)0.0143 (11)0.0004 (8)0.0016 (8)0.0010 (8)
C180.0110 (10)0.0111 (9)0.0197 (11)0.0002 (7)0.0006 (8)0.0012 (8)
C190.0123 (10)0.0190 (11)0.0160 (11)0.0004 (8)0.0049 (8)0.0007 (8)
C200.0144 (10)0.0159 (10)0.0130 (11)0.0004 (8)0.0017 (8)0.0016 (8)
C210.0129 (10)0.0105 (10)0.0172 (11)0.0008 (7)0.0003 (8)0.0005 (8)
C220.0119 (10)0.0230 (11)0.0188 (12)0.0010 (8)0.0009 (8)0.0016 (9)
C230.0130 (11)0.0244 (12)0.0241 (13)0.0003 (8)0.0021 (9)0.0046 (10)
C240.0113 (10)0.0253 (12)0.0214 (12)0.0024 (8)0.0013 (8)0.0025 (9)
C250.0113 (10)0.0202 (11)0.0209 (12)0.0016 (8)0.0008 (8)0.0027 (9)
Geometric parameters (Å, º) top
Cu—O21.9217 (15)C4—C51.386 (3)
Cu—O31.9289 (14)C4—H4A0.9300
Cu—N21.9967 (17)C5—C61.475 (3)
Cu—N11.9983 (18)C6—C71.396 (3)
Cu—O42.3760 (16)C7—C81.381 (3)
O1—C1.246 (3)C7—H70.9300
O2—C1.275 (2)C8—C91.383 (3)
O3—C111.282 (2)C8—H80.9300
O4—N61.269 (3)C9—C101.387 (3)
O5—N61.249 (3)C9—H90.9300
O6—N61.226 (3)C10—H100.9300
O7—N71.244 (3)C11—C121.417 (3)
O8—N71.257 (3)C11—C211.447 (3)
O9—N71.242 (3)C12—C131.379 (3)
O10—H30.857 (17)C13—H130.9300
O10—H40.847 (17)C14—C151.512 (3)
O11—H10.848 (17)C14—H14A0.9700
O11—H20.858 (17)C14—H14B0.9700
F—C191.360 (2)C15—H15A0.9600
N1—C11.336 (3)C15—H15B0.9600
N1—C51.358 (3)C15—H15C0.9600
N2—C101.338 (3)C16—C211.404 (3)
N2—C61.348 (3)C16—C171.408 (3)
N3—C131.338 (3)C17—C181.388 (3)
N3—C161.402 (3)C17—H170.9300
N3—C141.491 (3)C18—C191.414 (3)
N4—C181.405 (3)C19—C201.352 (3)
N4—C221.463 (3)C20—C211.407 (3)
N4—C251.475 (3)C20—H200.9300
N5—C241.488 (3)C22—C231.522 (3)
N5—C231.491 (3)C22—H22A0.9700
N5—H5A0.9000C22—H22B0.9700
N5—H5B0.9000C23—H23A0.9700
C—C121.503 (3)C23—H23B0.9700
C1—C21.383 (3)C24—C251.511 (3)
C1—H1A0.9300C24—H24A0.9700
C2—C31.384 (3)C24—H24B0.9700
C2—H2A0.9300C25—H25A0.9700
C3—C41.388 (3)C25—H25B0.9700
C3—H3A0.9300
O2—Cu—O393.45 (6)C10—C9—H9120.7
O2—Cu—N292.17 (7)N2—C10—C9121.8 (2)
O3—Cu—N2171.98 (7)N2—C10—H10119.1
O2—Cu—N1170.82 (6)C9—C10—H10119.1
O3—Cu—N192.60 (6)O3—C11—C12125.43 (18)
N2—Cu—N181.16 (7)O3—C11—C21118.04 (18)
O2—Cu—O489.69 (6)C12—C11—C21116.49 (18)
O3—Cu—O489.45 (6)C13—C12—C11119.04 (18)
N2—Cu—O496.31 (6)C13—C12—C116.56 (18)
N1—Cu—O497.27 (6)C11—C12—C124.26 (18)
C—O2—Cu126.64 (13)N3—C13—C12124.71 (19)
C11—O3—Cu121.03 (13)N3—C13—H13117.6
N6—O4—Cu112.59 (13)C12—C13—H13117.6
H3—O10—H4111 (2)N3—C14—C15114.55 (17)
H1—O11—H2108 (2)N3—C14—H14A108.6
C1—N1—C5119.11 (19)C15—C14—H14A108.6
C1—N1—Cu126.54 (14)N3—C14—H14B108.6
C5—N1—Cu114.21 (14)C15—C14—H14B108.6
C10—N2—C6119.68 (18)H14A—C14—H14B107.6
C10—N2—Cu126.00 (15)C14—C15—H15A109.5
C6—N2—Cu114.30 (14)C14—C15—H15B109.5
C13—N3—C16119.60 (18)H15A—C15—H15B109.5
C13—N3—C14121.63 (17)C14—C15—H15C109.5
C16—N3—C14118.77 (16)H15A—C15—H15C109.5
C18—N4—C22116.19 (17)H15B—C15—H15C109.5
C18—N4—C25114.54 (16)N3—C16—C21118.51 (17)
C22—N4—C25110.14 (16)N3—C16—C17121.03 (19)
C24—N5—C23111.55 (16)C21—C16—C17120.46 (19)
C24—N5—H5A109.3C18—C17—C16120.8 (2)
C23—N5—H5A109.3C18—C17—H17119.6
C24—N5—H5B109.3C16—C17—H17119.6
C23—N5—H5B109.3C17—C18—N4123.87 (19)
H5A—N5—H5B108.0C17—C18—C19116.98 (18)
O6—N6—O5120.4 (2)N4—C18—C19119.12 (18)
O6—N6—O4120.2 (2)C20—C19—F118.54 (19)
O5—N6—O4119.4 (2)C20—C19—C18123.34 (19)
O9—N7—O7120.5 (2)F—C19—C18118.10 (17)
O9—N7—O8119.0 (2)C19—C20—C21119.9 (2)
O7—N7—O8120.5 (2)C19—C20—H20120.1
O1—C—O2122.79 (18)C21—C20—H20120.1
O1—C—C12117.48 (18)C16—C21—C20118.52 (18)
O2—C—C12119.70 (18)C16—C21—C11121.63 (19)
N1—C1—C2122.30 (19)C20—C21—C11119.85 (19)
N1—C1—H1A118.8N4—C22—C23110.50 (18)
C2—C1—H1A118.8N4—C22—H22A109.6
C1—C2—C3118.6 (2)C23—C22—H22A109.6
C1—C2—H2A120.7N4—C22—H22B109.6
C3—C2—H2A120.7C23—C22—H22B109.6
C2—C3—C4119.7 (2)H22A—C22—H22B108.1
C2—C3—H3A120.2N5—C23—C22111.52 (17)
C4—C3—H3A120.2N5—C23—H23A109.3
C5—C4—C3118.6 (2)C22—C23—H23A109.3
C5—C4—H4A120.7N5—C23—H23B109.3
C3—C4—H4A120.7C22—C23—H23B109.3
N1—C5—C4121.6 (2)H23A—C23—H23B108.0
N1—C5—C6114.14 (19)N5—C24—C25109.68 (17)
C4—C5—C6124.22 (19)N5—C24—H24A109.7
N2—C6—C7121.5 (2)C25—C24—H24A109.7
N2—C6—C5114.90 (17)N5—C24—H24B109.7
C7—C6—C5123.6 (2)C25—C24—H24B109.7
C8—C7—C6118.3 (2)H24A—C24—H24B108.2
C8—C7—H7120.9N4—C25—C24110.20 (17)
C6—C7—H7120.9N4—C25—H25A109.6
C7—C8—C9120.1 (2)C24—C25—H25A109.6
C7—C8—H8119.9N4—C25—H25B109.6
C9—C8—H8119.9C24—C25—H25B109.6
C8—C9—C10118.6 (2)H25A—C25—H25B108.1
C8—C9—H9120.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—H3···O40.86 (2)2.02 (2)2.843 (3)161 (3)
O10—H3···O60.86 (2)2.49 (2)3.167 (4)137 (3)
O10—H3···N60.86 (2)2.57 (2)3.371 (3)157 (3)
O10—H4···O90.85 (2)2.03 (2)2.829 (3)156 (3)
O10—H4···O80.85 (2)2.65 (2)3.345 (3)140 (3)
O10—H4···N70.85 (2)2.70 (2)3.517 (3)163 (3)
O11—H1···O5i0.85 (2)1.99 (2)2.795 (3)157 (3)
O11—H2···O8ii0.86 (2)2.08 (2)2.908 (3)164 (3)
O11—H2···O7ii0.86 (2)2.40 (2)3.103 (3)139 (3)
O11—H2···N7ii0.86 (2)2.57 (2)3.417 (3)168 (3)
N5—H5A···O1iii0.901.792.686 (2)176
N5—H5B···O10i0.902.072.850 (3)144
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x+1, y+1, z; (iii) x1, y, z.
 

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