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In the solid state, the title compound, 8-{4-[4-(pyrimidin-2-yl)­piperazin-1-yl]but­yl}-8-aza­spiro­[4.5]decane-7,9-dione, C21H31N5O2, exists as an extended conformer with the piperazinyl and glutarimide units having chair and sofa conformations, respectively, while the butyl chain is trans,trans,trans.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047726/hg2129sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047726/hg2129Isup2.hkl
Contains datablock I

CCDC reference: 629910

Key indicators

  • Single-crystal X-ray study
  • T = 567 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.150
  • Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.94 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: KM-4 Software (Kuma Diffraction, 1999); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004).

8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-8-azaspiro[4,5]decane-7,9-dione top
Crystal data top
C21H31N5O2F(000) = 832
Mr = 385.51Dx = 1.230 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 50 reflections
a = 10.548 (2) Åθ = 6–22°
b = 11.764 (2) ŵ = 0.65 mm1
c = 16.998 (3) ÅT = 292 K
β = 99.28 (3)°Prism, colorless
V = 2081.6 (7) Å30.35 × 0.28 × 0.19 mm
Z = 4
Data collection top
Kuma KM4 four-circle
diffractometer
Rint = 0.046
Radiation source: fine-focus sealed tubeθmax = 81.3°, θmin = 4.3°
Graphite monochromatorh = 1313
ω–2θ scansk = 015
4454 measured reflectionsl = 021
4320 independent reflections3 standard reflections every 100 reflections
2791 reflections with I > 2σ(I) intensity decay: 0.1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.150 w = 1/[σ2(Fo2) + (0.08P)2 + 0.26P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
4320 reflectionsΔρmax = 0.20 e Å3
254 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0008 (2)
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
N10.65633 (17)0.29318 (15)0.12095 (10)0.0634 (4)
C20.58135 (17)0.20416 (15)0.13173 (10)0.0484 (4)
C40.6373 (2)0.1043 (2)0.02871 (12)0.0642 (5)
H40.63060.03980.00330.077*
N50.56743 (16)0.10915 (14)0.08718 (9)0.0558 (4)
C50.7181 (2)0.1888 (2)0.01329 (13)0.0702 (6)
H50.76640.18330.02770.084*
C60.7239 (2)0.2822 (2)0.06166 (13)0.0712 (6)
H60.77810.34140.05260.085*
N20.51537 (16)0.21005 (12)0.19382 (9)0.0540 (4)
C110.5056 (2)0.31577 (15)0.23694 (11)0.0555 (4)
H11A0.42720.35510.21460.067*
H11B0.57770.36460.23140.067*
C120.50501 (19)0.29129 (16)0.32412 (11)0.0543 (4)
H12A0.58660.25790.34730.065*
H12B0.49490.36190.35190.065*
N30.40118 (14)0.21389 (12)0.33457 (8)0.0458 (3)
C130.42048 (18)0.10728 (15)0.29413 (11)0.0511 (4)
H13A0.35320.05400.30160.061*
H13B0.50230.07440.31750.061*
C140.41867 (19)0.12625 (15)0.20606 (11)0.0547 (4)
H14A0.43580.05510.18090.066*
H14B0.33440.15270.18160.066*
C150.39634 (18)0.19628 (18)0.41919 (10)0.0547 (4)
H15A0.40450.26930.44600.066*
H15B0.46920.15010.44210.066*
C160.27429 (18)0.13927 (19)0.43495 (11)0.0567 (5)
H16A0.27060.06280.41340.068*
H16B0.20080.18090.40760.068*
C170.26603 (19)0.1336 (2)0.52312 (11)0.0617 (5)
H17A0.33250.08330.54950.074*
H17B0.28110.20870.54640.074*
C180.13605 (19)0.09098 (19)0.53696 (11)0.0579 (5)
H18A0.07000.14300.51220.069*
H18B0.11970.01730.51170.069*
N40.12816 (15)0.08068 (13)0.62232 (9)0.0503 (4)
C190.09726 (18)0.17800 (15)0.66237 (12)0.0526 (4)
O10.07278 (19)0.26518 (13)0.62565 (10)0.0817 (5)
C200.10124 (18)0.17056 (16)0.75032 (11)0.0516 (4)
H20A0.03990.22430.76560.062*
H20B0.18600.19330.77650.062*
C210.07164 (16)0.05300 (15)0.78065 (10)0.0466 (4)
C220.15831 (19)0.03164 (17)0.74689 (12)0.0588 (5)
H22A0.24600.01960.77310.071*
H22B0.13360.10790.76010.071*
C230.15520 (19)0.02485 (16)0.65882 (12)0.0567 (5)
O20.1778 (2)0.10608 (14)0.61948 (11)0.0919 (6)
C240.1339 (2)0.0819 (2)0.82513 (15)0.0759 (6)
H24A0.17450.15310.80650.091*
H24B0.19870.03210.84090.091*
C250.07245 (17)0.02654 (17)0.75916 (12)0.0558 (4)
H25A0.10740.05840.70760.067*
H25B0.08720.05490.75770.067*
C260.0284 (2)0.1028 (3)0.89458 (14)0.0813 (7)
H26A0.04920.06750.94250.098*
H26B0.01640.18360.90410.098*
C270.0918 (2)0.0502 (2)0.87194 (11)0.0634 (5)
H27A0.10240.02730.89130.076*
H27B0.16720.09370.89410.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0681 (10)0.0685 (11)0.0587 (10)0.0125 (8)0.0253 (8)0.0010 (8)
C20.0508 (9)0.0517 (9)0.0435 (9)0.0029 (7)0.0098 (7)0.0033 (7)
C40.0677 (12)0.0766 (14)0.0500 (11)0.0200 (11)0.0146 (9)0.0029 (9)
N50.0629 (9)0.0579 (9)0.0481 (8)0.0060 (7)0.0138 (7)0.0042 (7)
C50.0588 (11)0.1003 (17)0.0561 (12)0.0171 (11)0.0236 (9)0.0062 (12)
C60.0644 (12)0.0893 (16)0.0654 (13)0.0045 (11)0.0273 (10)0.0087 (12)
N20.0692 (10)0.0452 (8)0.0531 (9)0.0118 (7)0.0260 (7)0.0075 (6)
C110.0754 (12)0.0410 (8)0.0554 (11)0.0108 (8)0.0261 (9)0.0040 (8)
C120.0639 (11)0.0497 (9)0.0523 (10)0.0145 (8)0.0181 (8)0.0055 (8)
N30.0513 (7)0.0449 (7)0.0435 (7)0.0048 (6)0.0147 (6)0.0022 (6)
C130.0613 (10)0.0409 (8)0.0546 (10)0.0066 (7)0.0199 (8)0.0005 (7)
C140.0678 (11)0.0463 (9)0.0539 (10)0.0122 (8)0.0215 (8)0.0089 (8)
C150.0544 (10)0.0670 (12)0.0437 (9)0.0134 (8)0.0114 (7)0.0012 (8)
C160.0563 (10)0.0713 (12)0.0437 (9)0.0144 (9)0.0114 (8)0.0006 (8)
C170.0591 (11)0.0833 (14)0.0448 (10)0.0191 (10)0.0147 (8)0.0026 (9)
C180.0583 (10)0.0714 (12)0.0462 (10)0.0154 (9)0.0150 (8)0.0021 (9)
N40.0554 (8)0.0506 (8)0.0485 (8)0.0048 (6)0.0190 (6)0.0001 (6)
C190.0576 (10)0.0437 (9)0.0588 (10)0.0048 (8)0.0166 (8)0.0028 (8)
O10.1209 (15)0.0539 (8)0.0740 (10)0.0085 (9)0.0263 (9)0.0150 (7)
C200.0548 (9)0.0471 (9)0.0554 (10)0.0061 (8)0.0167 (8)0.0046 (8)
C210.0460 (8)0.0479 (9)0.0474 (9)0.0022 (7)0.0119 (7)0.0045 (7)
C220.0621 (11)0.0545 (10)0.0629 (11)0.0115 (9)0.0197 (9)0.0092 (9)
C230.0608 (11)0.0508 (10)0.0625 (11)0.0034 (8)0.0223 (9)0.0035 (9)
O20.1321 (16)0.0641 (10)0.0876 (12)0.0207 (10)0.0421 (11)0.0119 (8)
C240.0530 (11)0.0857 (16)0.0945 (17)0.0058 (11)0.0282 (11)0.0138 (13)
C250.0514 (10)0.0537 (10)0.0636 (11)0.0069 (8)0.0128 (8)0.0028 (8)
C260.0741 (14)0.114 (2)0.0604 (13)0.0151 (14)0.0245 (11)0.0004 (13)
C270.0611 (11)0.0812 (14)0.0491 (10)0.0086 (10)0.0124 (8)0.0083 (9)
Geometric parameters (Å, º) top
N1—C61.331 (3)C17—C181.514 (3)
N1—C21.343 (2)C17—H17A0.9700
C2—N51.345 (2)C17—H17B0.9700
C2—N21.356 (2)C18—N41.472 (2)
C4—N51.330 (2)C18—H18A0.9700
C4—C51.362 (3)C18—H18B0.9700
C4—H40.9300N4—C231.397 (2)
C5—C61.368 (3)N4—C191.397 (2)
C5—H50.9300C19—O11.207 (2)
C6—H60.9300C19—C201.491 (3)
N2—C111.456 (2)C20—C211.526 (2)
N2—C141.457 (2)C20—H20A0.9700
C11—C121.511 (2)C20—H20B0.9700
C11—H11A0.9700C21—C221.525 (2)
C11—H11B0.9700C21—C271.532 (2)
C12—N31.457 (2)C21—C251.537 (2)
C12—H12A0.9700C22—C231.494 (3)
C12—H12B0.9700C22—H22A0.9700
N3—C131.460 (2)C22—H22B0.9700
N3—C151.462 (2)C23—O21.212 (2)
C13—C141.511 (3)C24—C261.506 (3)
C13—H13A0.9700C24—C251.529 (3)
C13—H13B0.9700C24—H24A0.9700
C14—H14A0.9700C24—H24B0.9700
C14—H14B0.9700C25—H25A0.9700
C15—C161.513 (2)C25—H25B0.9700
C15—H15A0.9700C26—C271.515 (3)
C15—H15B0.9700C26—H26A0.9700
C16—C171.517 (2)C26—H26B0.9700
C16—H16A0.9700C27—H27A0.9700
C16—H16B0.9700C27—H27B0.9700
C6—N1—C2115.25 (19)C16—C17—H17B109.3
N1—C2—N5125.77 (16)H17A—C17—H17B108.0
N1—C2—N2116.99 (16)N4—C18—C17112.16 (16)
N5—C2—N2117.22 (16)N4—C18—H18A109.2
N5—C4—C5123.5 (2)C17—C18—H18A109.2
N5—C4—H4118.3N4—C18—H18B109.2
C5—C4—H4118.3C17—C18—H18B109.2
C4—N5—C2115.67 (18)H18A—C18—H18B107.9
C4—C5—C6116.06 (19)C23—N4—C19123.98 (15)
C4—C5—H5122.0C23—N4—C18118.12 (15)
C6—C5—H5122.0C19—N4—C18117.88 (16)
N1—C6—C5123.8 (2)O1—C19—N4119.46 (18)
N1—C6—H6118.1O1—C19—C20122.51 (18)
C5—C6—H6118.1N4—C19—C20117.99 (16)
C2—N2—C11121.48 (14)C19—C20—C21114.69 (15)
C2—N2—C14122.36 (15)C19—C20—H20A108.6
C11—N2—C14113.46 (14)C21—C20—H20A108.6
N2—C11—C12110.05 (15)C19—C20—H20B108.6
N2—C11—H11A109.6C21—C20—H20B108.6
C12—C11—H11A109.6H20A—C20—H20B107.6
N2—C11—H11B109.6C22—C21—C20107.28 (14)
C12—C11—H11B109.6C22—C21—C27111.92 (15)
H11A—C11—H11B108.2C20—C21—C27111.05 (16)
N3—C12—C11111.15 (15)C22—C21—C25114.10 (16)
N3—C12—H12A109.4C20—C21—C25110.60 (15)
C11—C12—H12A109.4C27—C21—C25101.92 (14)
N3—C12—H12B109.4C23—C22—C21115.11 (16)
C11—C12—H12B109.4C23—C22—H22A108.5
H12A—C12—H12B108.0C21—C22—H22A108.5
C12—N3—C13108.35 (13)C23—C22—H22B108.5
C12—N3—C15110.77 (14)C21—C22—H22B108.5
C13—N3—C15111.77 (14)H22A—C22—H22B107.5
N3—C13—C14111.05 (14)O2—C23—N4120.00 (19)
N3—C13—H13A109.4O2—C23—C22122.42 (19)
C14—C13—H13A109.4N4—C23—C22117.55 (16)
N3—C13—H13B109.4C26—C24—C25107.30 (18)
C14—C13—H13B109.4C26—C24—H24A110.3
H13A—C13—H13B108.0C25—C24—H24A110.3
N2—C14—C13110.13 (15)C26—C24—H24B110.3
N2—C14—H14A109.6C25—C24—H24B110.3
C13—C14—H14A109.6H24A—C24—H24B108.5
N2—C14—H14B109.6C24—C25—C21105.05 (16)
C13—C14—H14B109.6C24—C25—H25A110.7
H14A—C14—H14B108.1C21—C25—H25A110.7
N3—C15—C16113.74 (15)C24—C25—H25B110.7
N3—C15—H15A108.8C21—C25—H25B110.7
C16—C15—H15A108.8H25A—C25—H25B108.8
N3—C15—H15B108.8C24—C26—C27106.09 (19)
C16—C15—H15B108.8C24—C26—H26A110.5
H15A—C15—H15B107.7C27—C26—H26A110.5
C15—C16—C17112.36 (15)C24—C26—H26B110.5
C15—C16—H16A109.1C27—C26—H26B110.5
C17—C16—H16A109.1H26A—C26—H26B108.7
C15—C16—H16B109.1C26—C27—C21105.27 (16)
C17—C16—H16B109.1C26—C27—H27A110.7
H16A—C16—H16B107.9C21—C27—H27A110.7
C18—C17—C16111.47 (16)C26—C27—H27B110.7
C18—C17—H17A109.3C21—C27—H27B110.7
C16—C17—H17A109.3H27A—C27—H27B108.8
C18—C17—H17B109.3
C6—N1—C2—N51.8 (3)C17—C18—N4—C1984.1 (2)
C6—N1—C2—N2177.16 (19)C23—N4—C19—O1178.55 (19)
C5—C4—N5—C20.2 (3)C18—N4—C19—O13.2 (3)
N1—C2—N5—C41.5 (3)C23—N4—C19—C203.9 (3)
N2—C2—N5—C4177.50 (17)C18—N4—C19—C20174.36 (15)
N5—C4—C5—C60.5 (3)O1—C19—C20—C21152.9 (2)
C2—N1—C6—C51.0 (3)N4—C19—C20—C2129.6 (2)
C4—C5—C6—N10.1 (3)C19—C20—C21—C2251.4 (2)
N1—C2—N2—C1111.9 (3)C19—C20—C21—C27174.00 (15)
N5—C2—N2—C11169.08 (17)C19—C20—C21—C2573.6 (2)
N1—C2—N2—C14172.05 (18)C20—C21—C22—C2351.3 (2)
N5—C2—N2—C148.9 (3)C27—C21—C22—C23173.37 (17)
C2—N2—C11—C12145.26 (18)C25—C21—C22—C2371.5 (2)
C14—N2—C11—C1252.9 (2)C19—N4—C23—O2178.0 (2)
N2—C11—C12—N356.7 (2)C18—N4—C23—O23.8 (3)
C11—C12—N3—C1360.6 (2)C19—N4—C23—C223.6 (3)
C11—C12—N3—C15176.46 (16)C18—N4—C23—C22174.67 (16)
C12—N3—C13—C1460.48 (19)C21—C22—C23—O2152.5 (2)
C15—N3—C13—C14177.19 (14)C21—C22—C23—N429.1 (3)
C2—N2—C14—C13145.45 (18)C26—C24—C25—C2118.6 (3)
C11—N2—C14—C1352.9 (2)C22—C21—C25—C24155.03 (17)
N3—C13—C14—N256.5 (2)C20—C21—C25—C2483.9 (2)
C12—N3—C15—C16166.84 (17)C27—C21—C25—C2434.2 (2)
C13—N3—C15—C1672.2 (2)C25—C24—C26—C274.9 (3)
N3—C15—C16—C17173.9 (2)C24—C26—C27—C2126.8 (3)
C15—C16—C17—C18172.3 (2)C22—C21—C27—C26159.96 (19)
C16—C17—C18—N4177.7 (2)C20—C21—C27—C2680.2 (2)
C17—C18—N4—C2394.3 (2)C25—C21—C27—C2637.6 (2)
 

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