4-[4-(Piperidin-1-yl)piperidin-1-yl]benzonitrile

Xu, G.; Shi, J.; Chen, L.; Luo, Y.

doi:10.1107/S160053680905507X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o284

https://doi.org/10.1107/S160053680905507X

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4-[4-(Piperidin-1-yl)piperidin-1-yl]benzonitrile

Guo-bin Xu,^a Jian-you Shi,^a Li-juan Chen ^a and You-fu Luo ^a ^*

^aState Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu, Sichuan 610041, People's Republic of China
^*Correspondence e-mail: luo_youfu@scu.edu.cn

(Received 9 November 2009; accepted 22 December 2009; online 9 January 2010)

In the title compound, C₁₇H₂₃N₃, both piperidine rings adopt chair conformations. In the crystal packing, intermolecular C—H⋯N hydrogen bonds and C—H⋯π interactions are present.

Related literature

For general background, see: Pevarello et al. (2006 ).

Experimental

Crystal data

C₁₇H₂₃N₃
M_r = 269.38
Monoclinic, P 2₁ /c
a = 10.090 (2) Å
b = 11.100 (2) Å
c = 13.446 (3) Å
β = 100.72 (3)°
V = 1479.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 113 K
0.26 × 0.25 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.981, T_max = 0.986
11970 measured reflections
3500 independent reflections
2749 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.111
S = 1.12
3500 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cgⁱ	1.00	2.99	3.9363 (14)	158
C16—H16⋯N3ⁱⁱ	0.95	2.54	3.3442 (16)	143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ChemBioDraw Ultra CambridgeSoft (2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680905507X/kp2240sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680905507X/kp2240Isup2.hkl

checkCIF report

Comment top

4-(4-(Piperidin-1-yl)piperidin-1-yl)benzonitrile are key intermediates which can be used to synthesize 3-aminopyrazole derivatives, which can be used as precursors for anticancer and anti-malarial agents. In the structure of the title molecule (Fig. 1) both piperidine rings are in a chair conformation. A crystal packing is dominated by van der Waals interactions (Fig. 2).

Related literature top

For general background, see: Pevarello et al. (2006).

Experimental top

A DMSO solution of 1-(piperidin-4-yl)piperidine (4.37 g, 0.01 mol) with 4-fluorobenzonitrile (1.21 g, 0.01 mol) was heated to reflux for 3 h, then water (50 ml) was added into the solution. The mixture was extracted with CH₂Cl₂. After the solvent was removed a red crystalline powder was obtained; its recrystallisation from a methanol solution after 5 days yielded single crystals.

Structure description top

For general background, see: Pevarello et al. (2006).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ChemBioDraw Ultra (CambridgeSoft, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing of I dominated by van der Waals interactions.

4-[4-(Piperidin-1-yl)piperidin-1-yl]benzonitrile top

Crystal data top

C₁₇H₂₃N₃	F(000) = 584
M_r = 269.38	D_x = 1.209 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4488 reflections
a = 10.090 (2) Å	θ = 2.7–27.9°
b = 11.100 (2) Å	µ = 0.07 mm⁻¹
c = 13.446 (3) Å	T = 113 K
β = 100.72 (3)°	Block, red
V = 1479.7 (5) Å³	0.26 × 0.25 × 0.20 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3500 independent reflections
Radiation source: rotating anode	2749 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.032
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.8°
ω and φ scans	h = −13→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −14→14
T_min = 0.981, T_max = 0.986	l = −17→17
11970 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0612P)² + 0.0668P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
3500 reflections	Δρ_max = 0.27 e Å⁻³
182 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (7)

Crystal data top

C₁₇H₂₃N₃	V = 1479.7 (5) Å³
M_r = 269.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.090 (2) Å	µ = 0.07 mm⁻¹
b = 11.100 (2) Å	T = 113 K
c = 13.446 (3) Å	0.26 × 0.25 × 0.20 mm
β = 100.72 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3500 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2749 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.986	R_int = 0.032
11970 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.12	Δρ_max = 0.27 e Å⁻³
3500 reflections	Δρ_min = −0.19 e Å⁻³
182 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

	x	y	z	U_iso*/U_eq
N1	0.19321 (8)	0.59022 (8)	0.73578 (6)	0.0193 (2)
N2	0.26675 (8)	0.49828 (7)	0.43659 (6)	0.0187 (2)
N3	0.48688 (9)	0.35177 (8)	0.00345 (7)	0.0256 (2)
C1	0.21163 (10)	0.49931 (10)	0.81631 (8)	0.0225 (2)
H1A	0.3069	0.4727	0.8304	0.027*
H1B	0.1547	0.4283	0.7934	0.027*
C2	0.17411 (11)	0.54896 (10)	0.91273 (8)	0.0270 (3)
H2A	0.2363	0.6154	0.9391	0.032*
H2B	0.1839	0.4848	0.9647	0.032*
C3	0.02945 (11)	0.59541 (11)	0.89283 (9)	0.0310 (3)
H3A	−0.0339	0.5270	0.8768	0.037*
H3B	0.0102	0.6360	0.9542	0.037*
C4	0.00956 (11)	0.68349 (11)	0.80492 (9)	0.0307 (3)
H4A	0.0638	0.7569	0.8249	0.037*
H4B	−0.0865	0.7074	0.7881	0.037*
C5	0.05156 (10)	0.62790 (11)	0.71205 (8)	0.0274 (3)
H5A	−0.0062	0.5573	0.6894	0.033*
H5B	0.0392	0.6875	0.6563	0.033*
C6	0.24849 (10)	0.54949 (9)	0.64737 (8)	0.0182 (2)
H6	0.3448	0.5272	0.6733	0.022*
C7	0.18209 (10)	0.43925 (9)	0.59102 (8)	0.0205 (2)
H7A	0.1816	0.3721	0.6394	0.025*
H7B	0.0873	0.4584	0.5608	0.025*
C8	0.25693 (10)	0.40038 (9)	0.50799 (8)	0.0204 (2)
H8A	0.3488	0.3734	0.5391	0.024*
H8B	0.2093	0.3313	0.4708	0.024*
C9	0.32454 (11)	0.60897 (9)	0.48736 (8)	0.0224 (2)
H9A	0.3206	0.6742	0.4366	0.027*
H9B	0.4206	0.5948	0.5172	0.027*
C10	0.25036 (11)	0.64891 (9)	0.56997 (8)	0.0229 (2)
H10A	0.1566	0.6711	0.5394	0.027*
H10B	0.2951	0.7211	0.6042	0.027*
C11	0.31345 (9)	0.46754 (9)	0.34801 (7)	0.0179 (2)
C12	0.32252 (10)	0.55520 (9)	0.27405 (8)	0.0209 (2)
H12	0.2976	0.6360	0.2849	0.025*
C13	0.36689 (10)	0.52613 (9)	0.18606 (8)	0.0212 (2)
H13	0.3727	0.5870	0.1374	0.025*
C14	0.40341 (10)	0.40774 (9)	0.16801 (8)	0.0182 (2)
C15	0.39452 (10)	0.31974 (9)	0.24037 (8)	0.0203 (2)
H15	0.4191	0.2390	0.2289	0.024*
C16	0.35023 (10)	0.34886 (9)	0.32857 (8)	0.0205 (2)
H16	0.3445	0.2876	0.3770	0.025*
C17	0.45003 (10)	0.37726 (9)	0.07679 (8)	0.0200 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0189 (4)	0.0234 (5)	0.0162 (4)	0.0020 (3)	0.0049 (3)	−0.0006 (3)
N2	0.0253 (4)	0.0146 (4)	0.0169 (4)	−0.0026 (3)	0.0060 (3)	−0.0002 (3)
N3	0.0337 (5)	0.0195 (5)	0.0252 (5)	−0.0013 (4)	0.0101 (4)	−0.0025 (4)
C1	0.0240 (5)	0.0248 (5)	0.0194 (5)	0.0000 (4)	0.0053 (4)	0.0015 (4)
C2	0.0287 (6)	0.0343 (6)	0.0190 (6)	−0.0034 (5)	0.0071 (4)	−0.0014 (5)
C3	0.0272 (6)	0.0414 (7)	0.0273 (6)	−0.0046 (5)	0.0127 (5)	−0.0073 (5)
C4	0.0237 (5)	0.0400 (7)	0.0300 (6)	0.0065 (5)	0.0085 (5)	−0.0051 (5)
C5	0.0215 (5)	0.0370 (6)	0.0237 (6)	0.0071 (5)	0.0044 (4)	−0.0020 (5)
C6	0.0183 (5)	0.0197 (5)	0.0170 (5)	0.0005 (4)	0.0045 (4)	−0.0008 (4)
C7	0.0226 (5)	0.0200 (5)	0.0196 (5)	−0.0024 (4)	0.0058 (4)	0.0011 (4)
C8	0.0272 (5)	0.0160 (5)	0.0189 (5)	−0.0022 (4)	0.0069 (4)	0.0008 (4)
C9	0.0287 (5)	0.0187 (5)	0.0210 (5)	−0.0062 (4)	0.0076 (4)	−0.0031 (4)
C10	0.0315 (6)	0.0177 (5)	0.0212 (6)	−0.0024 (4)	0.0094 (4)	−0.0023 (4)
C11	0.0178 (5)	0.0183 (5)	0.0170 (5)	−0.0011 (4)	0.0018 (4)	−0.0009 (4)
C12	0.0263 (5)	0.0161 (5)	0.0209 (5)	0.0028 (4)	0.0059 (4)	0.0000 (4)
C13	0.0268 (5)	0.0187 (5)	0.0185 (5)	0.0012 (4)	0.0054 (4)	0.0027 (4)
C14	0.0196 (5)	0.0181 (5)	0.0171 (5)	−0.0009 (4)	0.0033 (4)	−0.0014 (4)
C15	0.0238 (5)	0.0164 (5)	0.0205 (6)	0.0007 (4)	0.0033 (4)	−0.0017 (4)
C16	0.0253 (5)	0.0170 (5)	0.0187 (5)	−0.0007 (4)	0.0031 (4)	0.0011 (4)
C17	0.0236 (5)	0.0145 (5)	0.0216 (6)	−0.0012 (4)	0.0038 (4)	0.0000 (4)

Geometric parameters (Å, º) top

N1—C5	1.4663 (13)	C6—H6	1.0000
N1—C1	1.4664 (13)	C7—C8	1.5219 (14)
N1—C6	1.4749 (13)	C7—H7A	0.9900
N2—C11	1.4020 (13)	C7—H7B	0.9900
N2—C8	1.4656 (13)	C8—H8A	0.9900
N2—C9	1.4723 (13)	C8—H8B	0.9900
N3—C17	1.1520 (13)	C9—C10	1.5164 (14)
C1—C2	1.5200 (14)	C9—H9A	0.9900
C1—H1A	0.9900	C9—H9B	0.9900
C1—H1B	0.9900	C10—H10A	0.9900
C2—C3	1.5241 (16)	C10—H10B	0.9900
C2—H2A	0.9900	C11—C16	1.4063 (14)
C2—H2B	0.9900	C11—C12	1.4064 (14)
C3—C4	1.5183 (17)	C12—C13	1.3788 (14)
C3—H3A	0.9900	C12—H12	0.9500
C3—H3B	0.9900	C13—C14	1.3981 (14)
C4—C5	1.5220 (15)	C13—H13	0.9500
C4—H4A	0.9900	C14—C15	1.3933 (14)
C4—H4B	0.9900	C14—C17	1.4335 (14)
C5—H5A	0.9900	C15—C16	1.3811 (14)
C5—H5B	0.9900	C15—H15	0.9500
C6—C10	1.5195 (14)	C16—H16	0.9500
C6—C7	1.5269 (14)

C5—N1—C1	109.98 (8)	C8—C7—H7A	109.4
C5—N1—C6	114.29 (8)	C6—C7—H7A	109.4
C1—N1—C6	111.67 (8)	C8—C7—H7B	109.4
C11—N2—C8	116.77 (8)	C6—C7—H7B	109.4
C11—N2—C9	115.49 (8)	H7A—C7—H7B	108.0
C8—N2—C9	112.59 (8)	N2—C8—C7	111.93 (8)
N1—C1—C2	111.27 (9)	N2—C8—H8A	109.2
N1—C1—H1A	109.4	C7—C8—H8A	109.2
C2—C1—H1A	109.4	N2—C8—H8B	109.2
N1—C1—H1B	109.4	C7—C8—H8B	109.2
C2—C1—H1B	109.4	H8A—C8—H8B	107.9
H1A—C1—H1B	108.0	N2—C9—C10	112.14 (8)
C1—C2—C3	110.81 (9)	N2—C9—H9A	109.2
C1—C2—H2A	109.5	C10—C9—H9A	109.2
C3—C2—H2A	109.5	N2—C9—H9B	109.2
C1—C2—H2B	109.5	C10—C9—H9B	109.2
C3—C2—H2B	109.5	H9A—C9—H9B	107.9
H2A—C2—H2B	108.1	C9—C10—C6	111.10 (8)
C4—C3—C2	109.76 (9)	C9—C10—H10A	109.4
C4—C3—H3A	109.7	C6—C10—H10A	109.4
C2—C3—H3A	109.7	C9—C10—H10B	109.4
C4—C3—H3B	109.7	C6—C10—H10B	109.4
C2—C3—H3B	109.7	H10A—C10—H10B	108.0
H3A—C3—H3B	108.2	N2—C11—C16	121.86 (9)
C3—C4—C5	111.16 (10)	N2—C11—C12	120.57 (9)
C3—C4—H4A	109.4	C16—C11—C12	117.55 (9)
C5—C4—H4A	109.4	C13—C12—C11	121.27 (9)
C3—C4—H4B	109.4	C13—C12—H12	119.4
C5—C4—H4B	109.4	C11—C12—H12	119.4
H4A—C4—H4B	108.0	C12—C13—C14	120.46 (9)
N1—C5—C4	110.24 (9)	C12—C13—H13	119.8
N1—C5—H5A	109.6	C14—C13—H13	119.8
C4—C5—H5A	109.6	C15—C14—C13	118.98 (9)
N1—C5—H5B	109.6	C15—C14—C17	120.39 (9)
C4—C5—H5B	109.6	C13—C14—C17	120.63 (9)
H5A—C5—H5B	108.1	C16—C15—C14	120.57 (9)
N1—C6—C10	112.59 (8)	C16—C15—H15	119.7
N1—C6—C7	116.67 (8)	C14—C15—H15	119.7
C10—C6—C7	107.60 (8)	C15—C16—C11	121.17 (9)
N1—C6—H6	106.4	C15—C16—H16	119.4
C10—C6—H6	106.4	C11—C16—H16	119.4
C7—C6—H6	106.4	N3—C17—C14	179.37 (11)
C8—C7—C6	111.06 (8)

C5—N1—C1—C2	−60.67 (11)	N2—C9—C10—C6	56.38 (12)
C6—N1—C1—C2	171.35 (8)	N1—C6—C10—C9	172.41 (8)
N1—C1—C2—C3	56.80 (12)	C7—C6—C10—C9	−57.65 (11)
C1—C2—C3—C4	−52.73 (12)	C8—N2—C11—C16	−0.48 (13)
C2—C3—C4—C5	53.76 (12)	C9—N2—C11—C16	135.34 (10)
C1—N1—C5—C4	60.92 (12)	C8—N2—C11—C12	178.25 (9)
C6—N1—C5—C4	−172.56 (9)	C9—N2—C11—C12	−45.93 (12)
C3—C4—C5—N1	−58.25 (12)	N2—C11—C12—C13	−179.30 (9)
C5—N1—C6—C10	63.26 (11)	C16—C11—C12—C13	−0.52 (14)
C1—N1—C6—C10	−171.10 (8)	C11—C12—C13—C14	0.37 (15)
C5—N1—C6—C7	−61.87 (12)	C12—C13—C14—C15	−0.13 (15)
C1—N1—C6—C7	63.77 (11)	C12—C13—C14—C17	−179.78 (9)
N1—C6—C7—C8	−174.76 (8)	C13—C14—C15—C16	0.05 (15)
C10—C6—C7—C8	57.63 (11)	C17—C14—C15—C16	179.70 (9)
C11—N2—C8—C7	−169.71 (8)	C14—C15—C16—C11	−0.21 (15)
C9—N2—C8—C7	53.24 (11)	N2—C11—C16—C15	179.21 (9)
C6—C7—C8—N2	−56.30 (11)	C12—C11—C16—C15	0.44 (15)
C11—N2—C9—C10	169.02 (8)	C15—C14—C17—N3	38 (9)
C8—N2—C9—C10	−53.35 (11)	C13—C14—C17—N3	−142 (9)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cgⁱ	1.00	2.99	3.9363 (14)	158
C16—H16···N3ⁱⁱ	0.95	2.54	3.3442 (16)	143

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₃N₃
M_r	269.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	10.090 (2), 11.100 (2), 13.446 (3)
β (°)	100.72 (3)
V (Å³)	1479.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.26 × 0.25 × 0.20

Data collection
Diffractometer	Rigaku Saturn CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.981, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	11970, 3500, 2749
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.111, 1.12
No. of reflections	3500
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.19

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ChemBioDraw Ultra (CambridgeSoft, 2008).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cgⁱ	1.00	2.99	3.9363 (14)	158
C16—H16···N3ⁱⁱ	0.95	2.54	3.3442 (16)	143

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+1/2, z+1/2.

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

CambridgeSoft (2008). ChemBioDraw Ultra. CambridgeSoft, England. Google Scholar
Pevarello, P., Fancelli, D., Vulpetti, A., Amici, R., Villa, M., Pittalà, V., Vianello, P., Cameron, A., Ciomei, M., Mercurio, C., Bischoff, J. R., Roletto, F., Varasi, M. & Brasca, M. G. (2006). Bioorg. Med. Chem. Lett. 16, 1084–1090. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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