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(4-Chloro­benzohydrazidato-κ2N′,O)[2-(4-chloro­benzoyl­hydrazono-κ2N,O)propionato(2−)-κO]oxidovanadium(V)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 21 May 2009; accepted 26 May 2009; online 6 June 2009)

In the crystal structure of the title compound, [VO(C7H6ClN2O)(C10H7ClN2O3)], the VV atom is N,O-chelated by the chloro­benzoyl­hydrazidate anion and O,N,O′-chelated by the (chloro­benzoyl­hydrazono)propionate dianion. The distorted octa­hedral trans-N2O4 coordination geometry is completed by the vanadyl O atom. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into a linear chain parallel to [010].

Related literature

For the analogous vanadyl complex without the chlorine substituent in the two ligands, see: Wong et al. (2009[Wong, H. W., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m422.]).

[Scheme 1]

Experimental

Crystal data
  • [V(C7H6ClN2O)(C10H7ClN2O3)O]

  • Mr = 475.15

  • Monoclinic, C 2/c

  • a = 26.628 (2) Å

  • b = 5.7109 (3) Å

  • c = 24.772 (1) Å

  • β = 100.396 (3)°

  • V = 3705.2 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.86 mm−1

  • T = 119 K

  • 0.40 × 0.04 × 0.04 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.724, Tmax = 0.966

  • 11303 measured reflections

  • 4189 independent reflections

  • 2154 reflections with I > 2σ(I)

  • Rint = 0.174

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.175

  • S = 0.97

  • 4189 reflections

  • 239 parameters

  • H-atom parameters constrained

  • Δρmax = 1.40 e Å−3

  • Δρmin = −1.20 e Å−3

Table 1
Selected bond lengths (Å)

V1—N1 2.064 (4)
V1—N4 1.888 (4)
V1—O1 1.988 (4)
V1—O3 1.989 (3)
V1—O4 2.207 (4)
V1—O5 1.593 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3⋯O2i 0.88 1.92 2.744 (5) 156
N4—H4⋯O1i 0.88 2.14 2.840 (5) 136
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the analogous vanadyl complex without the chlorine substituent in the two ligands, see: Wong et al. (2009).

Experimental top

2-[p-Chlorobenzoylhydrazono]propionic acid was prepared from the condensation reaction of p-chlorobenzhydrazide and pyruvic acid. The compound (0.70 g, 3 mmol) and vanadyl sulfate (0.25 g, 1.5 mmol) in 20 ml of distilled water were heated for 5 h. Slow evaporation of the filtrate gave orange crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The nitrogen-bound H-atoms were similarly treated (N–H 0.88 Å).

All phenylene rings were refined was rigid hexagons of 1.39 Å sides.

The final difference Fourier map had a large peak/deep hole in the vicnity of the V1 atom.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of VO(C7H6ClN2O)(C10H7ClN2O3) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
(4-Chlorobenzohydrazidato-κ2N',O)[2-(4- chlorobenzoylhydrazono-κ2N,O)propionato(2-)- κO]oxidovanadium(V) top
Crystal data top
[V(C7H6ClN2O)(C10H7ClN2O3)O]F(000) = 1920
Mr = 475.15Dx = 1.704 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 957 reflections
a = 26.628 (2) Åθ = 2.5–23.1°
b = 5.7109 (3) ŵ = 0.86 mm1
c = 24.772 (1) ÅT = 119 K
β = 100.396 (3)°Prism, orange
V = 3705.2 (4) Å30.40 × 0.04 × 0.04 mm
Z = 8
Data collection top
Bruker SMART APEX
diffractometer
4189 independent reflections
Radiation source: fine-focus sealed tube2154 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.174
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3434
Tmin = 0.724, Tmax = 0.966k = 77
11303 measured reflectionsl = 3230
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0714P)2]
where P = (Fo2 + 2Fc2)/3
4189 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 1.40 e Å3
0 restraintsΔρmin = 1.20 e Å3
Crystal data top
[V(C7H6ClN2O)(C10H7ClN2O3)O]V = 3705.2 (4) Å3
Mr = 475.15Z = 8
Monoclinic, C2/cMo Kα radiation
a = 26.628 (2) ŵ = 0.86 mm1
b = 5.7109 (3) ÅT = 119 K
c = 24.772 (1) Å0.40 × 0.04 × 0.04 mm
β = 100.396 (3)°
Data collection top
Bruker SMART APEX
diffractometer
4189 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2154 reflections with I > 2σ(I)
Tmin = 0.724, Tmax = 0.966Rint = 0.174
11303 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0590 restraints
wR(F2) = 0.175H-atom parameters constrained
S = 0.97Δρmax = 1.40 e Å3
4189 reflectionsΔρmin = 1.20 e Å3
239 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
V10.66692 (3)0.32434 (15)0.27882 (4)0.0216 (3)
Cl10.44158 (5)0.7483 (2)0.46938 (6)0.0289 (4)
Cl20.84139 (5)0.6026 (2)0.53131 (6)0.0294 (4)
O10.67515 (13)0.1122 (6)0.21738 (17)0.0236 (9)
O20.63441 (13)0.1245 (6)0.15164 (17)0.0281 (9)
O30.62899 (12)0.4195 (6)0.33748 (16)0.0237 (9)
O40.69433 (12)0.0349 (6)0.33560 (16)0.0222 (9)
O50.65919 (13)0.5607 (6)0.24415 (18)0.0296 (10)
N10.60013 (15)0.1326 (7)0.2650 (2)0.0203 (10)
N20.56469 (15)0.1678 (7)0.2986 (2)0.0236 (11)
N30.76603 (15)0.2341 (7)0.34041 (19)0.0206 (10)
H30.79900.25550.35160.025*
N40.73671 (15)0.3820 (7)0.3060 (2)0.0215 (10)
H40.75060.51060.29580.026*
C10.63701 (18)0.0159 (9)0.1950 (3)0.0228 (12)
C20.59319 (18)0.0213 (9)0.2266 (2)0.0225 (12)
C30.55037 (18)0.1879 (9)0.2136 (3)0.0280 (14)
H3A0.55210.30160.24350.042*
H3B0.55260.27020.17940.042*
H3C0.51800.10250.20920.042*
C40.58356 (18)0.3289 (8)0.3341 (3)0.0221 (12)
C50.55047 (11)0.4234 (5)0.37140 (15)0.0196 (12)
C60.50488 (12)0.3112 (5)0.37506 (15)0.0239 (13)
H60.49650.16710.35650.029*
C70.47159 (10)0.4100 (5)0.40592 (17)0.0249 (13)
H7A0.44040.33330.40840.030*
C80.48390 (11)0.6209 (5)0.43310 (15)0.0227 (12)
C90.52949 (12)0.7331 (5)0.42944 (15)0.0239 (12)
H90.53790.87720.44800.029*
C100.56278 (10)0.6343 (5)0.39859 (16)0.0254 (13)
H100.59390.71100.39610.031*
C110.74052 (18)0.0506 (8)0.3562 (2)0.0186 (12)
C120.76740 (11)0.1137 (5)0.39758 (13)0.0222 (13)
C130.73990 (8)0.3013 (5)0.41306 (14)0.0245 (13)
H130.70540.32490.39580.029*
C140.76286 (11)0.4543 (5)0.45377 (15)0.0241 (12)
H140.74410.58250.46440.029*
C150.81333 (11)0.4198 (5)0.47899 (13)0.0251 (13)
C160.84083 (9)0.2323 (6)0.46350 (14)0.0273 (13)
H160.87530.20870.48070.033*
C170.81787 (10)0.0792 (5)0.42280 (15)0.0251 (13)
H170.83670.04890.41220.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
V10.0156 (4)0.0218 (5)0.0292 (7)0.0012 (4)0.0087 (4)0.0014 (4)
Cl10.0244 (6)0.0351 (8)0.0291 (9)0.0057 (5)0.0097 (6)0.0082 (6)
Cl20.0273 (7)0.0282 (7)0.0332 (10)0.0029 (6)0.0066 (6)0.0046 (7)
O10.0189 (17)0.0246 (19)0.028 (2)0.0046 (15)0.0074 (17)0.0015 (17)
O20.0217 (18)0.040 (2)0.024 (3)0.0046 (17)0.0079 (17)0.004 (2)
O30.0151 (16)0.0256 (19)0.031 (3)0.0022 (14)0.0067 (17)0.0060 (18)
O40.0150 (16)0.0225 (18)0.029 (3)0.0032 (14)0.0048 (17)0.0022 (17)
O50.0269 (19)0.025 (2)0.039 (3)0.0037 (16)0.013 (2)0.0060 (19)
N10.018 (2)0.019 (2)0.027 (3)0.0043 (17)0.011 (2)0.003 (2)
N20.018 (2)0.024 (2)0.032 (3)0.0009 (18)0.014 (2)0.004 (2)
N30.0137 (19)0.025 (2)0.023 (3)0.0018 (17)0.0037 (18)0.005 (2)
N40.020 (2)0.018 (2)0.028 (3)0.0018 (17)0.009 (2)0.000 (2)
C10.016 (2)0.020 (3)0.033 (4)0.003 (2)0.004 (2)0.001 (3)
C20.016 (2)0.021 (3)0.030 (4)0.004 (2)0.004 (2)0.003 (3)
C30.018 (2)0.032 (3)0.036 (4)0.004 (2)0.010 (3)0.007 (3)
C40.018 (2)0.017 (2)0.032 (4)0.000 (2)0.005 (2)0.004 (3)
C50.019 (2)0.020 (3)0.021 (3)0.002 (2)0.006 (2)0.003 (2)
C60.022 (2)0.021 (3)0.029 (4)0.003 (2)0.006 (2)0.007 (3)
C70.021 (3)0.021 (3)0.034 (4)0.000 (2)0.009 (3)0.001 (3)
C80.022 (2)0.023 (3)0.023 (3)0.005 (2)0.006 (2)0.004 (2)
C90.026 (3)0.026 (3)0.019 (3)0.000 (2)0.003 (2)0.005 (2)
C100.017 (2)0.028 (3)0.033 (4)0.001 (2)0.006 (2)0.003 (3)
C110.017 (2)0.022 (3)0.017 (3)0.003 (2)0.005 (2)0.004 (2)
C120.019 (2)0.018 (3)0.031 (4)0.002 (2)0.011 (2)0.008 (2)
C130.016 (2)0.024 (3)0.036 (4)0.003 (2)0.011 (2)0.006 (3)
C140.026 (3)0.024 (3)0.023 (3)0.002 (2)0.006 (2)0.000 (3)
C150.023 (3)0.027 (3)0.027 (4)0.007 (2)0.009 (3)0.002 (3)
C160.014 (2)0.032 (3)0.035 (4)0.001 (2)0.003 (2)0.003 (3)
C170.023 (3)0.024 (3)0.029 (4)0.003 (2)0.007 (3)0.005 (3)
Geometric parameters (Å, º) top
V1—N12.064 (4)C3—H3C0.9800
V1—N41.888 (4)C4—C51.489 (5)
V1—O11.988 (4)C5—C61.3900
V1—O31.989 (3)C5—C101.3900
V1—O42.207 (4)C6—C71.3900
V1—O51.593 (4)C6—H60.9500
Cl1—C81.724 (2)C7—C81.3900
Cl2—C151.726 (3)C7—H7A0.9500
O1—C11.293 (6)C8—C91.3900
O2—C11.231 (6)C9—C101.3900
O3—C41.305 (5)C9—H90.9500
O4—C111.247 (6)C10—H100.9500
N1—C21.284 (7)C11—C121.476 (6)
N1—N21.381 (5)C12—C131.3900
N2—C41.308 (7)C12—C171.3900
N3—N41.344 (6)C13—C141.3900
N3—C111.345 (6)C13—H130.9500
N3—H30.8800C14—C151.3900
N4—H40.8800C14—H140.9500
C1—C21.518 (7)C15—C161.3900
C2—C31.475 (7)C16—C171.3900
C3—H3A0.9800C16—H160.9500
C3—H3B0.9800C17—H170.9500
O5—V1—N493.89 (19)O3—C4—C5117.5 (4)
O5—V1—O197.17 (18)N2—C4—C5118.3 (4)
N4—V1—O198.17 (16)C6—C5—C10120.0
O5—V1—O397.41 (17)C6—C5—C4119.7 (3)
N4—V1—O3106.77 (17)C10—C5—C4120.1 (3)
O1—V1—O3150.05 (14)C5—C6—C7120.0
O5—V1—N1109.67 (19)C5—C6—H6120.0
N4—V1—N1156.21 (18)C7—C6—H6120.0
O1—V1—N176.15 (15)C8—C7—C6120.0
O3—V1—N174.34 (15)C8—C7—H7A120.0
O5—V1—O4166.80 (18)C6—C7—H7A120.0
N4—V1—O473.27 (16)C9—C8—C7120.0
O1—V1—O487.83 (14)C9—C8—Cl1120.02 (18)
O3—V1—O483.82 (14)C7—C8—Cl1119.94 (18)
N1—V1—O483.36 (15)C10—C9—C8120.0
C1—O1—V1119.1 (3)C10—C9—H9120.0
C4—O3—V1115.6 (3)C8—C9—H9120.0
C11—O4—V1113.3 (3)C9—C10—C5120.0
C2—N1—N2121.6 (4)C9—C10—H10120.0
C2—N1—V1119.4 (3)C5—C10—H10120.0
N2—N1—V1119.0 (3)O4—C11—N3116.7 (5)
C4—N2—N1106.6 (4)O4—C11—C12123.9 (4)
N4—N3—C11114.1 (4)N3—C11—C12119.4 (4)
N4—N3—H3123.0C13—C12—C17120.0
C11—N3—H3123.0C13—C12—C11117.9 (3)
N3—N4—V1122.6 (3)C17—C12—C11122.0 (3)
N3—N4—H4118.7C12—C13—C14120.0
V1—N4—H4118.7C12—C13—H13120.0
O2—C1—O1125.1 (5)C14—C13—H13120.0
O2—C1—C2120.8 (5)C13—C14—C15120.0
O1—C1—C2114.1 (5)C13—C14—H14120.0
N1—C2—C3127.3 (5)C15—C14—H14120.0
N1—C2—C1110.3 (4)C16—C15—C14120.0
C3—C2—C1122.4 (5)C16—C15—Cl2119.67 (19)
C2—C3—H3A109.5C14—C15—Cl2120.29 (19)
C2—C3—H3B109.5C15—C16—C17120.0
H3A—C3—H3B109.5C15—C16—H16120.0
C2—C3—H3C109.5C17—C16—H16120.0
H3A—C3—H3C109.5C16—C17—C12120.0
H3B—C3—H3C109.5C16—C17—H17120.0
O3—C4—N2124.2 (5)C12—C17—H17120.0
O5—V1—O1—C1101.5 (4)O1—C1—C2—N19.8 (6)
N4—V1—O1—C1163.5 (4)O2—C1—C2—C312.0 (8)
O3—V1—O1—C117.1 (6)O1—C1—C2—C3169.0 (5)
N1—V1—O1—C17.1 (4)V1—O3—C4—N26.8 (7)
O4—V1—O1—C190.8 (4)V1—O3—C4—C5170.4 (3)
O5—V1—O3—C4104.1 (4)N1—N2—C4—O34.5 (7)
N4—V1—O3—C4159.6 (4)N1—N2—C4—C5172.6 (4)
O1—V1—O3—C414.5 (5)O3—C4—C5—C6170.8 (4)
N1—V1—O3—C44.3 (4)N2—C4—C5—C611.9 (6)
O4—V1—O3—C489.1 (4)O3—C4—C5—C1015.1 (6)
O5—V1—O4—C1114.2 (9)N2—C4—C5—C10162.2 (4)
N4—V1—O4—C110.7 (3)C10—C5—C6—C70.0
O1—V1—O4—C1198.5 (3)C4—C5—C6—C7174.2 (4)
O3—V1—O4—C11110.3 (3)C5—C6—C7—C80.0
N1—V1—O4—C11174.8 (4)C6—C7—C8—C90.0
O5—V1—N1—C291.9 (4)C6—C7—C8—Cl1177.7 (3)
N4—V1—N1—C279.5 (6)C7—C8—C9—C100.0
O1—V1—N1—C20.8 (4)Cl1—C8—C9—C10177.7 (3)
O3—V1—N1—C2175.6 (4)C8—C9—C10—C50.0
O4—V1—N1—C290.2 (4)C6—C5—C10—C90.0
O5—V1—N1—N290.2 (4)C4—C5—C10—C9174.1 (4)
N4—V1—N1—N298.4 (5)V1—O4—C11—N31.1 (6)
O1—V1—N1—N2177.0 (4)V1—O4—C11—C12176.7 (3)
O3—V1—N1—N22.2 (3)N4—N3—C11—O43.1 (7)
O4—V1—N1—N287.6 (4)N4—N3—C11—C12174.9 (4)
C2—N1—N2—C4178.1 (5)O4—C11—C12—C132.1 (6)
V1—N1—N2—C40.3 (5)N3—C11—C12—C13179.9 (3)
C11—N3—N4—V14.0 (6)O4—C11—C12—C17174.7 (4)
O5—V1—N4—N3179.5 (4)N3—C11—C12—C173.1 (5)
O1—V1—N4—N382.7 (4)C17—C12—C13—C140.0
O3—V1—N4—N380.5 (4)C11—C12—C13—C14176.9 (3)
N1—V1—N4—N38.6 (7)C12—C13—C14—C150.0
O4—V1—N4—N32.5 (4)C13—C14—C15—C160.0
V1—O1—C1—O2167.7 (4)C13—C14—C15—Cl2177.6 (3)
V1—O1—C1—C211.3 (6)C14—C15—C16—C170.0
N2—N1—C2—C33.4 (8)Cl2—C15—C16—C17177.6 (3)
V1—N1—C2—C3174.5 (4)C15—C16—C17—C120.0
N2—N1—C2—C1177.9 (4)C13—C12—C17—C160.0
V1—N1—C2—C14.3 (6)C11—C12—C17—C16176.8 (3)
O2—C1—C2—N1169.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O2i0.881.922.744 (5)156
N4—H4···O1i0.882.142.840 (5)136
Symmetry code: (i) x+3/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[V(C7H6ClN2O)(C10H7ClN2O3)O]
Mr475.15
Crystal system, space groupMonoclinic, C2/c
Temperature (K)119
a, b, c (Å)26.628 (2), 5.7109 (3), 24.772 (1)
β (°) 100.396 (3)
V3)3705.2 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.86
Crystal size (mm)0.40 × 0.04 × 0.04
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.724, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
11303, 4189, 2154
Rint0.174
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.175, 0.97
No. of reflections4189
No. of parameters239
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.40, 1.20

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top
V1—N12.064 (4)V1—O31.989 (3)
V1—N41.888 (4)V1—O42.207 (4)
V1—O11.988 (4)V1—O51.593 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O2i0.881.922.744 (5)156
N4—H4···O1i0.882.142.840 (5)136
Symmetry code: (i) x+3/2, y+1/2, z+1/2.
 

Acknowledgements

We thank the University of Malaya (RG020/09AFR) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar
First citationWong, H. W., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m422.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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