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In the title complex, [Zn(C18H17N2O3)(C2H3O2)(C9H7N)], the ZnII atom is coordinated by two O atoms and one N atom from the tridentate hydrazone ligand, the N atom from the quinoline mol­ecule and one O atom from the acetate group, leading to a distorted trigonal bipyramidal environment for the metal atom. The two O atoms of the deprotonated hydrazone ligand occupy the axial sites. A hydrogen-bonded dimer is formed through intermolecular hydrogen bonds across a center of inversion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804009808/ng6024sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804009808/ng6024Isup2.hkl
Contains datablock I

CCDC reference: 239115

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.120
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Zn1 - O5 .. 17.43 su
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C7 .. 5.83 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - O4 .. 7.62 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... O5 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C28
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 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 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(Acetato-κO)[benzoylacetone (4-methoxybenzoyl)hydrazonato- κ3O,O',N](quinoline-κN)zinc(II) top
Crystal data top
[Zn(C18H17N2O3)(C2H3O2)(C9H7N)]Z = 2
Mr = 562.93F(000) = 584
Triclinic, P1Dx = 1.402 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.529 (1) ÅCell parameters from 6783 reflections
b = 11.471 (1) Åθ = 3.0–27.3°
c = 12.633 (2) ŵ = 0.97 mm1
α = 94.391 (9)°T = 293 K
β = 95.409 (8)°Prism, yellow
γ = 102.888 (5)°0.37 × 0.24 × 0.19 mm
V = 1333.2 (3) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6036 independent reflections
Radiation source: fine-focus sealed tube4880 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.0°
ω scansh = 1112
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1414
Tmin = 0.717, Tmax = 0.838l = 1616
12738 measured reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0716P)2 + 0.2421P]
where P = (Fo2 + 2Fc2)/3
6036 reflections(Δ/σ)max = 0.001
346 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.34 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.73388 (3)0.34612 (2)0.81804 (2)0.0476 (1)
N10.7654 (2)0.4481 (2)0.9632 (1)0.0449 (4)
N20.8512 (2)0.4087 (2)1.0422 (1)0.0448 (4)
N30.5382 (2)0.2068 (2)0.8222 (2)0.0474 (4)
O10.6322 (2)0.4614 (2)0.7532 (1)0.0573 (4)
O20.8472 (2)0.2489 (2)0.9249 (1)0.0547 (4)
O31.2088 (2)0.0924 (2)1.3093 (1)0.0670 (5)
O40.8153 (2)0.2915 (2)0.6853 (1)0.0544 (4)
O50.9814 (2)0.4380 (2)0.7739 (2)0.0688 (5)
C10.4432 (3)0.5572 (3)0.6309 (2)0.0617 (6)
C20.3579 (3)0.6098 (3)0.5638 (2)0.0715 (8)
C30.3282 (3)0.7172 (3)0.5965 (3)0.0745 (8)
C40.3826 (4)0.7708 (3)0.6963 (3)0.090 (1)
C50.4685 (4)0.7187 (3)0.7644 (2)0.0752 (8)
C60.5005 (2)0.6104 (2)0.7330 (2)0.0492 (5)
C70.5926 (2)0.5489 (2)0.8020 (2)0.0456 (5)
C80.6260 (2)0.5867 (2)0.9105 (2)0.0481 (5)
C90.7106 (2)0.5413 (2)0.9887 (2)0.0449 (5)
C100.7356 (3)0.6038 (2)1.0998 (2)0.0551 (6)
C110.8901 (2)0.3057 (2)1.0150 (2)0.0440 (5)
C120.9798 (2)0.2563 (2)1.0946 (2)0.0426 (5)
C130.9989 (3)0.2913 (2)1.2035 (2)0.0531 (6)
C141.0784 (3)0.2366 (2)1.2729 (2)0.0579 (6)
C151.1380 (3)0.1439 (2)1.2344 (2)0.0491 (5)
C161.1203 (3)0.1085 (2)1.1257 (2)0.0485 (5)
C171.0426 (2)0.1650 (2)1.0571 (2)0.0455 (5)
C181.2650 (4)0.0078 (3)1.2756 (3)0.088 (1)
C190.5142 (3)0.1664 (2)0.9152 (2)0.0555 (6)
C200.3878 (3)0.0849 (3)0.9333 (2)0.0650 (7)
C210.2810 (3)0.0444 (3)0.8508 (2)0.0651 (7)
C220.3002 (3)0.0846 (2)0.7498 (2)0.0546 (6)
C230.1954 (3)0.0456 (3)0.6589 (3)0.0739 (8)
C240.2209 (3)0.0848 (3)0.5634 (2)0.0809 (9)
C250.3514 (3)0.1653 (3)0.5518 (2)0.0702 (8)
C260.4555 (3)0.2058 (2)0.6363 (2)0.0557 (6)
C270.4321 (2)0.1660 (2)0.7376 (2)0.0457 (5)
C280.9393 (3)0.3615 (2)0.6957 (2)0.0537 (6)
C291.0360 (4)0.3497 (4)0.6095 (3)0.103 (1)
H10.46280.48430.60710.074*
H20.32040.57190.49600.086*
H30.27160.75310.55120.089*
H40.36190.84350.71930.108*
H50.50510.75730.83210.090*
H80.58770.65020.93500.058*
H10A0.72300.54511.15040.066*
H10B0.66750.65341.10750.066*
H10C0.83240.65311.11260.066*
H130.95780.35211.23010.064*
H141.09200.26181.34560.070*
H161.16070.04711.09920.058*
H171.03180.14150.98410.055*
H18A1.18720.07181.24170.106*
H18B1.31200.03481.33650.106*
H18C1.33380.01561.22590.106*
H190.58580.19380.97250.067*
H200.37690.05881.00060.078*
H210.19600.00950.86120.078*
H230.10830.00770.66570.089*
H240.15140.05830.50460.097*
H250.36730.19160.48510.084*
H260.54140.25940.62730.067*
H29A1.04530.41810.56930.123*
H29B0.99440.27780.56270.123*
H29C1.13000.34560.64160.123*
H300.87750.44781.10430.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0548 (2)0.0449 (2)0.0423 (2)0.0150 (1)0.0033 (1)0.0010 (1)
N10.048 (1)0.044 (1)0.0417 (9)0.0117 (8)0.0032 (8)0.0021 (8)
N20.049 (1)0.044 (1)0.0398 (9)0.0110 (8)0.0039 (8)0.0015 (7)
N30.051 (1)0.050 (1)0.042 (1)0.0131 (9)0.0036 (8)0.0051 (8)
O10.072 (1)0.055 (1)0.0497 (9)0.0302 (9)0.0023 (8)0.0013 (7)
O20.067 (1)0.0512 (9)0.0455 (9)0.0232 (8)0.0110 (7)0.0050 (7)
O30.093 (1)0.060 (1)0.051 (1)0.034 (1)0.0138 (9)0.0040 (8)
O40.0507 (9)0.0543 (9)0.054 (1)0.0055 (8)0.0023 (7)0.0007 (8)
O50.065 (1)0.056 (1)0.077 (1)0.0108 (9)0.011 (1)0.0086 (9)
C10.070 (2)0.062 (2)0.056 (2)0.025 (1)0.002 (1)0.007 (1)
C20.074 (2)0.083 (2)0.056 (2)0.021 (2)0.008 (1)0.011 (1)
C30.066 (2)0.088 (2)0.076 (2)0.030 (2)0.003 (1)0.027 (2)
C40.118 (3)0.080 (2)0.086 (2)0.059 (2)0.005 (2)0.008 (2)
C50.099 (2)0.070 (2)0.063 (2)0.042 (2)0.011 (2)0.000 (1)
C60.045 (1)0.050 (1)0.052 (1)0.009 (1)0.007 (1)0.011 (1)
C70.043 (1)0.042 (1)0.050 (1)0.0072 (9)0.0030 (9)0.0086 (9)
C80.049 (1)0.0455 (1)0.050 (1)0.013 (1)0.004 (1)0.003 (1)
C90.041 (1)0.045 (1)0.047 (1)0.0073 (9)0.0042 (9)0.0018 (9)
C100.059 (1)0.059 (1)0.049 (1)0.022 (1)0.002 (1)0.003 (1)
C110.044 (1)0.043 (1)0.043 (1)0.0062 (9)0.0005 (9)0.0032 (9)
C120.040 (1)0.041 (1)0.042 (1)0.0035 (9)0.0004 (8)0.0040 (9)
C130.069 (2)0.046 (1)0.047 (1)0.021 (1)0.002 (1)0.001 (1)
C140.082 (2)0.054 (1)0.038 (1)0.022 (1)0.005 (1)0.002 (1)
C150.056 (1)0.044 (1)0.046 (1)0.011 (1)0.004 (1)0.0062 (9)
C160.051 (1)0.046 (1)0.048 (1)0.013 (1)0.003 (1)0.001 (1)
C170.047 (1)0.048 (1)0.040 (1)0.010 (1)0.0010 (9)0.0008 (9)
C180.126 (3)0.069 (2)0.077 (2)0.055 (2)0.018 (2)0.005 (2)
C190.057 (1)0.065 (2)0.046 (1)0.018 (1)0.005 (1)0.008 (1)
C200.074 (2)0.075 (2)0.055 (2)0.024 (2)0.020 (1)0.022 (1)
C210.059 (2)0.066 (2)0.072 (2)0.008 (1)0.021 (1)0.015 (1)
C220.051 (1)0.054 (1)0.058 (1)0.008 (1)0.009 (1)0.006 (1)
C230.053 (2)0.081 (2)0.075 (2)0.008 (1)0.000 (1)0.005 (2)
C240.061 (2)0.103 (2)0.060 (2)0.010 (2)0.011 (1)0.003 (2)
C250.066 (2)0.088 (2)0.046 (1)0.002 (2)0.005 (1)0.007 (1)
C260.052 (1)0.062 (2)0.046 (1)0.001 (1)0.001 (1)0.008 (1)
C270.046 (1)0.044 (1)0.046 (1)0.011 (1)0.0030 (9)0.0019 (9)
C280.050 (1)0.054 (1)0.056 (1)0.012 (1)0.000 (1)0.006 (1)
C290.071 (2)0.137 (4)0.095 (3)0.009 (2)0.0270 (19)0.004 (2)
Geometric parameters (Å, º) top
Zn1—N12.058 (2)C10—H10C0.9600
Zn1—N32.176 (2)C11—C121.485 (3)
Zn1—O11.987 (2)C12—c131.387 (3)
Zn1—O22.174 (2)C12—C171.393 (3)
Zn1—O42.027 (2)C13—C141.380 (3)
N1—C91.322 (3)C13—H130.9300
O2—C111.252 (3)C14—C151.390 (3)
C7—C81.390 (3)C14—H140.9300
N1—N21.395 (2)C15—C161.386 (3)
N2—C111.344 (3)C16—C171.378 (3)
O1—C71.283 (3)C16—H160.9300
C8—C91.419 (3)C17—H170.9300
Zn1—C282.591 (3)C18—H18A0.9600
N2—H300.8600C18—H18B0.9600
N3—C191.318 (3)C18—H18C0.9600
N3—C271.376 (3)C19—C201.400 (4)
O3—C151.357 (3)C19—H190.9300
O3—C181.425 (3)C20—C211.361 (4)
O4—C281.261 (3)C20—H200.9300
O5—C281.242 (3)C21—C221.404 (4)
C1—C21.383 (4)C21—H210.9300
C1—C61.390 (4)C22—C271.417 (3)
C1—H10.9300C22—C231.422 (4)
C2—C31.367 (5)C23—C241.344 (4)
C2—H20.9300C23—H230.9300
C3—C41.361 (5)C24—C251.402 (4)
C3—H30.9300C24—H240.9300
C4—C51.390 (4)C25—C261.363 (3)
C4—H40.9300C25—H250.9300
C5—C61.382 (4)C26—C271.412 (3)
C5—H50.9300C26—H260.9300
C6—C71.502 (3)C28—C291.508 (4)
C8—H80.9300C29—H29A0.9600
C9—C101.499 (3)C29—H29B0.9600
C10—H10A0.9600C29—H29C0.9600
C10—H10B0.9600
N1—Zn1—N3105.54 (8)C9—C10—H10A109.5
N1—Zn1—O275.77 (7)C9—C10—H10B109.5
O1—Zn1—N190.07 (7)C9—C10—H10C109.5
O1—Zn1—N395.17 (8)C11—N2—N1115.8 (2)
O1—Zn1—O2165.82 (7)C11—N2—H30122.1
O1—Zn1—O497.59 (7)C11—O2—Zn1112.9 (1)
O2—Zn1—N388.04 (7)C12—C13—H13119.7
O4—Zn1—N1149.27 (8)C12—C17—H17119.3
O4—Zn1—N3103.35 (7)C13—C12—C11124.3 (2)
O4—Zn1—O295.08 (7)C13—C12—C17118.4 (2)
N1—Zn1—C28120.99 (8)C13—C14—C15120.3 (2)
N1—N2—H30122.1C13—C14—H14119.9
N1—C9—C8120.7 (2)C14—C13—C12120.6 (2)
N1—C9—C10122.0 (2)C14—C13—H13119.7
N2—N1—Zn1114.0 (1)C15—O3—C18118.6 (2)
N2—C11—C12119.5 (2)C15—C14—H14119.9
N3—Zn1—C28131.19 (8)C15—C16—H16120.2
N3—C19—C20124.2 (2)C16—C15—C14119.7 (2)
N3—C19—H19117.9C16—C17—C12121.4 (2)
N3—C27—C22121.5 (2)C16—C17—H17119.3
N3—C27—C26119.1 (2)C17—C12—C11117.2 (2)
O1—Zn1—C2898.48 (8)C17—C16—C15119.6 (2)
O1—C7—C6114.9 (2)C17—C16—H16120.2
O1—C7—C8125.3 (2)C19—N3—Zn1117.2 (2)
O2—Zn1—C2889.66 (7)C19—N3—C27117.7 (2)
O2—C11—N2120.8 (2)C19—C20—H20120.5
O2—C11—C12119.7 (2)C20—C19—H19117.9
O3—C15—C14115.9 (2)C20—C21—C22119.5 (3)
O3—C15—C16124.5 (2)C20—C21—H21120.3
O3—C18—H18A109.5C21—C20—C19118.9 (2)
O3—C18—H18B109.5C21—C20—H20120.5
O3—C18—H18C109.5C21—C22—C23123.2 (3)
O4—Zn1—C2828.49 (7)C21—C22—C27118.2 (2)
O4—C28—Zn150.1 (1)C22—C21—H21120.3
O4—C28—C29117.8 (3)C22—C23—H23119.6
O5—C28—Zn171.5 (2)C23—C24—C25120.5 (3)
O5—C28—O4121.6 (2)C23—C24—H24119.8
O5—C28—C29120.6 (3)C24—C23—C22120.7 (3)
C1—C2—H2119.8C24—C23—H23119.6
C1—C6—C7119.1 (2)C24—C25—H25119.4
C2—C1—C6121.7 (3)C25—C24—H24119.8
C2—C1—H1119.2C25—C26—C27119.6 (2)
C2—C3—H3120.4C25—C26—H26120.2
C3—C2—C1120.3 (3)C26—C25—C24121.2 (3)
C3—C2—H2119.8C26—C25—H25119.4
C3—C4—C5121.0 (3)C26—C27—C22119.4 (2)
C3—C4—H4119.5C27—N3—Zn1124.9 (2)
C4—C3—C2119.1 (3)C27—C22—C23118.6 (2)
C4—C3—H3120.4C27—C26—H26120.2
C4—C5—H5119.5C28—O4—Zn1101.4 (2)
C5—C4—H4119.5C28—C29—H29A109.5
C5—C6—C1116.9 (2)C28—C29—H29B109.5
C5—C6—C7123.9 (2)C28—C29—H29C109.5
C6—C1—H1119.2C29—C28—Zn1167.8 (2)
C6—C5—C4120.9 (3)H10A—C10—H10B109.5
C6—C5—H5119.5H10A—C10—H10C109.5
C7—O1—Zn1127.2 (2)H10B—C10—H10C109.5
C7—C8—C9128.6 (2)H18A—C18—H18B109.5
C7—C8—H8115.7H18A—C18—H18C109.5
C8—C7—C6119.8 (2)H18B—C18—H18C109.5
C8—C9—C10117.3 (2)H29A—C29—H29B109.5
C9—N1—Zn1127.3 (2)H29A—C29—H29C109.5
C9—N1—N2118.6 (2)H29B—C29—H29C109.5
C9—C8—H8115.7
Zn1—N1—N2—C115.3 (2)O4—Zn1—N1—N269.1 (2)
Zn1—N1—C9—C84.0 (3)O4—Zn1—N1—C9113.2 (2)
Zn1—N1—C9—C10176.5 (2)O4—Zn1—N3—C19135.7 (2)
Zn1—N3—C19—C20174.2 (2)O4—Zn1—N3—C2750.5 (2)
Zn1—N3—C27—C22172.8 (2)O4—Zn1—O1—C7159.3 (2)
Zn1—N3—C27—C267.3 (3)O4—Zn1—O2—C11142.6 (2)
Zn1—O1—C7—C6172.3 (2)O4—Zn1—C28—O5179.6 (2)
Zn1—O1—C7—C86.4 (3)O4—Zn1—C28—C293 (1)
Zn1—O2—C11—N27.6 (3)C1—C2—C3—C40.7 (5)
Zn1—O2—C11—C12175.1 (2)C1—C6—C7—O111.9 (3)
Zn1—O4—C28—O50.5 (3)C1—C6—C7—C8166.8 (2)
Zn1—O4—C28—C29179.4 (3)C2—C1—C6—C50.2 (4)
N1—Zn1—N3—C1933.7 (2)C2—C1—C6—C7179.9 (3)
N1—Zn1—N3—C27140.1 (2)C2—C3—C4—C50.7 (6)
N1—Zn1—O1—C79.1 (2)C3—C4—C5—C60.5 (6)
N1—Zn1—O2—C117.7 (2)C4—C5—C6—C10.2 (5)
N1—Zn1—O4—C289.3 (2)C4—C5—C6—C7179.9 (3)
N1—Zn1—C28—O4174.5 (1)C5—C6—C7—O1167.8 (3)
N1—Zn1—C28—O55.1 (2)C5—C6—C7—C813.5 (4)
N1—Zn1—C28—C29177 (1)C6—C1—C2—C30.4 (5)
N1—N2—C11—O21.9 (3)C6—C7—C8—C9179.9 (2)
N1—N2—C11—C12179.2 (2)C7—C8—C9—N12.6 (4)
N2—N1—C9—C8178.3 (2)C7—C8—C9—C10176.9 (2)
N2—N1—C9—C101.2 (3)C9—N1—N2—C11172.7 (2)
N2—C11—C12—C1316.4 (3)C11—C12—C13—C14176.8 (2)
N2—C11—C12—C17166.8 (2)C11—C12—C17—C16176.0 (2)
N3—Zn1—N1—N290.4 (2)C12—C13—C14—C151.2 (4)
N3—Zn1—N1—C987.3 (2)C13—C12—C17—C161.0 (3)
N3—Zn1—O1—C796.5 (2)C13—C14—C15—O3177.2 (2)
N3—Zn1—O2—C11114.2 (2)C13—C14—C15—C161.5 (4)
N3—Zn1—O4—C28169.0 (1)C14—C15—C16—C170.6 (4)
N3—Zn1—C28—O414.3 (2)C15—C16—C17—C120.7 (4)
N3—Zn1—C28—O5165.3 (1)C17—C12—C13—C140.0 (4)
N3—Zn1—C28—C2916 (1)C18—O3—C15—C14176.3 (3)
N3—C19—C20—C210.6 (4)C18—O3—C15—C162.3 (4)
O1—Zn1—N1—N2174.2 (2)C19—N3—C27—C221.0 (3)
O1—Zn1—N1—C98.1 (2)C19—N3—C27—C26178.9 (2)
O1—Zn1—N3—C19125.2 (2)C19—C20—C21—C220.3 (4)
O1—Zn1—N3—C2748.6 (2)C20—C21—C22—C23179.0 (3)
O1—Zn1—O2—C1110.8 (4)C21—C22—C23—C24178.3 (3)
O1—Zn1—O4—C2893.8 (2)C21—C22—C27—N31.2 (4)
O1—Zn1—C28—O490.3 (2)C21—C22—C27—C26178.6 (2)
O1—Zn1—C28—O590.1 (2)C22—C23—C24—C250.2 (6)
O1—Zn1—C28—C2988 (1)C23—C22—C27—N3179.7 (2)
O1—C7—C8—C91.5 (4)C23—C22—C27—C260.1 (4)
O2—Zn1—N1—N26.6 (1)C23—C24—C25—C260.0 (6)
O2—Zn1—N1—C9171.2 (2)C24—C25—C26—C270.2 (5)
O2—Zn1—N3—C1940.9 (2)C25—C26—C27—N3179.6 (3)
O2—Zn1—N3—C27145.2 (2)C25—C26—C27—C220.2 (4)
O2—Zn1—O1—C76.1 (4)C27—N3—C19—C200.1 (4)
O2—Zn1—O4—C2879.8 (2)C27—C22—C23—C240.1 (5)
O2—Zn1—C28—O4101.3 (2)C28—Zn1—N1—N274.2 (2)
O2—Zn1—C28—O578.2 (2)C28—Zn1—N1—C9108.0 (2)
O2—Zn1—C28—C29104 (1)C28—Zn1—N3—C19128.8 (2)
O2—C11—C12—C13161.0 (2)C28—Zn1—N3—C2757.4 (2)
O2—C11—C12—C1715.8 (3)C28—Zn1—O1—C7130.5 (2)
O3—C15—C16—C17178.1 (2)C28—Zn1—O2—C11114.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H30···O5i0.862.102.909 (3)157
Symmetry code: (i) x+2, y+1, z+2.
 

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