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The title compound, C22H32N2O, is a member of the family of nociceptin receptor ligands derived from N-(4-piperidinyl)-2-indolinones. Modifications of the piperidine N-substituent can produce both agonists and antagonists, with the title compound being a weak agonist. The mol­ecule lies on a crystallographic mirror plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008682/lh6199sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008682/lh6199Isup2.hkl
Contains datablock I

CCDC reference: 239252

Key indicators

  • Single-crystal X-ray study
  • T = 103 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.093
  • Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT410_ALERT_2_C Short Intra H...H Contact H12A .. H15A .. 1.97 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.26 From the CIF: _reflns_number_total 1224 Count of symmetry unique reflns 1252 Completeness (_total/calc) 97.76% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2000) and XPREP (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1-[1-(4-isopropylcyclohexyl)piperidin-4-yl]indolin-2-one top
Crystal data top
C22H32N2OF(000) = 372
Mr = 340.50Dx = 1.205 Mg m3
Monoclinic, CmMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yCell parameters from 3559 reflections
a = 7.9959 (7) Åθ = 3.6–28.3°
b = 6.8268 (7) ŵ = 0.07 mm1
c = 17.2125 (17) ÅT = 103 K
β = 92.670 (2)°Plate, colorless
V = 938.55 (16) Å30.42 × 0.26 × 0.09 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD
diffractometer
1224 independent reflections
Radiation source: sealed tube1189 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 28.3°, θmin = 3.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1010
Tmin = 0.891, Tmax = 0.993k = 89
3852 measured reflectionsl = 2221
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) = 0.093H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0566P)2 + 0.1948P]
where P = (Fo2 + 2Fc2)/3
1224 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.26 e Å3
2 restraintsΔρmin = 0.21 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*/UeqOcc. (<1)
N10.9392 (2)0.00001.10724 (11)0.0155 (4)
C20.7822 (3)0.00001.13831 (13)0.0167 (5)
O20.6486 (2)0.00001.10067 (10)0.0202 (4)
C30.8074 (3)0.00001.22674 (13)0.0164 (4)
H3A0.75730.11811.24960.020*0.50
H3B0.75730.11811.24960.020*0.50
C40.9945 (3)0.00001.23969 (13)0.0148 (4)
C51.0963 (3)0.00001.30722 (13)0.0188 (5)
H5A1.04860.00001.35670.023*
C61.2709 (3)0.00001.30141 (13)0.0193 (5)
H6A1.34190.00001.34720.023*
C71.3401 (3)0.00001.22885 (13)0.0178 (5)
H7A1.45840.00001.22590.021*
C81.2398 (3)0.00001.15997 (13)0.0159 (4)
H8A1.28780.00001.11050.019*
C91.0669 (3)0.00001.16673 (12)0.0137 (4)
C100.9683 (3)0.00001.02327 (12)0.0161 (5)
H10A1.09220.00001.01760.019*
C110.8985 (2)0.1830 (2)0.98263 (8)0.0173 (3)
H11A0.95200.30101.00620.021*
H11B0.77650.19180.98950.021*
C120.9319 (2)0.1753 (2)0.89556 (9)0.0184 (3)
H12A0.88480.29410.86980.022*
H12B1.05420.17510.88900.022*
N130.8573 (2)0.00000.85762 (11)0.0146 (4)
C140.8845 (3)0.00000.77274 (12)0.0144 (4)
H14A1.00280.00000.76530.017*
C150.8076 (2)0.1819 (2)0.73277 (9)0.0193 (4)
H15A0.86170.30060.75540.023*
H15B0.68700.18800.74310.023*
C160.8280 (2)0.1815 (2)0.64442 (9)0.0200 (4)
H16A0.77320.29980.62170.024*
H16B0.94870.18920.63430.024*
C170.7534 (3)0.00000.60374 (12)0.0152 (4)
H17A0.63010.00000.61100.018*
C180.7810 (3)0.00000.51531 (13)0.0186 (5)
H18A0.89950.00000.50860.022*
C190.7079 (3)0.1821 (3)0.47441 (11)0.0306 (4)
H19A0.72930.17590.41890.046*
H19B0.76070.29970.49720.046*
H19C0.58690.18720.48100.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0146 (9)0.0199 (9)0.0120 (8)0.0000.0000 (7)0.000
C20.0207 (12)0.0146 (10)0.0149 (9)0.0000.0032 (9)0.000
O20.0158 (8)0.0260 (9)0.0186 (7)0.0000.0013 (6)0.000
C30.0181 (11)0.0186 (10)0.0127 (9)0.0000.0020 (8)0.000
C40.0163 (11)0.0140 (10)0.0140 (10)0.0000.0011 (8)0.000
C50.0229 (12)0.0200 (11)0.0133 (9)0.0000.0007 (9)0.000
C60.0227 (12)0.0179 (11)0.0165 (10)0.0000.0058 (9)0.000
C70.0150 (11)0.0167 (11)0.0213 (11)0.0000.0023 (9)0.000
C80.0161 (11)0.0155 (10)0.0161 (10)0.0000.0019 (8)0.000
C90.0166 (10)0.0121 (10)0.0122 (9)0.0000.0019 (8)0.000
C100.0143 (11)0.0222 (11)0.0118 (10)0.0000.0006 (8)0.000
C110.0238 (8)0.0157 (7)0.0125 (7)0.0013 (6)0.0007 (6)0.0010 (6)
C120.0234 (8)0.0175 (8)0.0141 (7)0.0037 (6)0.0003 (6)0.0008 (6)
N130.0187 (10)0.0131 (8)0.0120 (8)0.0000.0003 (7)0.000
C140.0153 (10)0.0157 (11)0.0122 (9)0.0000.0009 (8)0.000
C150.0300 (9)0.0142 (8)0.0136 (7)0.0044 (7)0.0014 (6)0.0005 (6)
C160.0296 (9)0.0166 (8)0.0137 (7)0.0018 (7)0.0008 (6)0.0017 (6)
C170.0170 (11)0.0160 (10)0.0126 (9)0.0000.0008 (8)0.000
C180.0208 (12)0.0217 (12)0.0135 (10)0.0000.0020 (9)0.000
C190.0455 (12)0.0296 (10)0.0165 (7)0.0073 (8)0.0006 (7)0.0039 (7)
Geometric parameters (Å, º) top
N1—C21.387 (3)C12—N131.4760 (19)
N1—C91.412 (3)C12—H12A0.9900
N1—C101.475 (3)C12—H12B0.9900
C2—O21.224 (3)N13—C12i1.4760 (19)
C2—C31.526 (3)N13—C141.487 (2)
C3—C41.502 (3)C14—C15i1.5345 (19)
C3—H3A0.9900C14—C151.5345 (19)
C3—H3B0.9900C14—H14A0.9600
C4—C51.388 (3)C15—C161.5369 (19)
C4—C91.407 (3)C15—H15A0.9900
C5—C61.404 (3)C15—H15B0.9900
C5—H5A0.9500C16—C171.531 (2)
C6—C71.389 (3)C16—H16A0.9900
C6—H6A0.9500C16—H16B0.9900
C7—C81.400 (3)C17—C16i1.531 (2)
C7—H7A0.9500C17—C181.548 (3)
C8—C91.393 (3)C17—H17A1.0000
C8—H8A0.9500C18—C19i1.531 (2)
C10—C11i1.525 (2)C18—C191.531 (2)
C10—C111.525 (2)C18—H18A0.9600
C10—H10A1.0000C19—H19A0.9800
C11—C121.535 (2)C19—H19B0.9800
C11—H11A0.9900C19—H19C0.9800
C11—H11B0.9900
C2—N1—C9110.92 (18)C11—C12—H12A109.2
C2—N1—C10124.40 (19)N13—C12—H12B109.2
C9—N1—C10124.69 (18)C11—C12—H12B109.2
O2—C2—N1125.4 (2)H12A—C12—H12B107.9
O2—C2—C3126.8 (2)C12—N13—C12i108.39 (18)
N1—C2—C3107.75 (19)C12—N13—C14111.10 (11)
C4—C3—C2103.43 (18)C12i—N13—C14111.10 (11)
C4—C3—H3A111.1N13—C14—C15i111.50 (11)
C2—C3—H3A111.1N13—C14—C15111.50 (11)
C4—C3—H3B111.1C15i—C14—C15108.07 (18)
C2—C3—H3B111.1N13—C14—H14A108.7
H3A—C3—H3B109.0C15i—C14—H14A108.5
C5—C4—C9119.9 (2)C15—C14—H14A108.5
C5—C4—C3131.7 (2)C14—C15—C16112.55 (14)
C9—C4—C3108.40 (18)C14—C15—H15A109.1
C4—C5—C6119.1 (2)C16—C15—H15A109.1
C4—C5—H5A120.4C14—C15—H15B109.1
C6—C5—H5A120.4C16—C15—H15B109.1
C7—C6—C5120.2 (2)H15A—C15—H15B107.8
C7—C6—H6A119.9C17—C16—C15113.40 (14)
C5—C6—H6A119.9C17—C16—H16A108.9
C6—C7—C8121.7 (2)C15—C16—H16A108.9
C6—C7—H7A119.2C17—C16—H16B108.9
C8—C7—H7A119.2C15—C16—H16B108.9
C9—C8—C7117.4 (2)H16A—C16—H16B107.7
C9—C8—H8A121.3C16—C17—C16i108.13 (18)
C7—C8—H8A121.3C16—C17—C18112.31 (12)
C8—C9—C4121.72 (19)C16i—C17—C18112.31 (12)
C8—C9—N1128.78 (19)C16—C17—H17A108.0
C4—C9—N1109.50 (19)C16i—C17—H17A108.0
N1—C10—C11i112.23 (11)C18—C17—H17A108.0
N1—C10—C11112.23 (11)C19i—C18—C19108.6 (2)
C11i—C10—C11110.03 (18)C19i—C18—C17112.54 (14)
N1—C10—H10A107.4C19—C18—C17112.54 (13)
C11i—C10—H10A107.4C19i—C18—H18A107.6
C11—C10—H10A107.4C19—C18—H18A107.6
C10—C11—C12110.06 (14)C17—C18—H18A107.8
C10—C11—H11A109.6C18—C19—H19A109.5
C12—C11—H11A109.6C18—C19—H19B109.5
C10—C11—H11B109.6H19A—C19—H19B109.5
C12—C11—H11B109.6C18—C19—H19C109.5
H11A—C11—H11B108.2H19A—C19—H19C109.5
N13—C12—C11112.00 (13)H19B—C19—H19C109.5
N13—C12—H12A109.2
C9—N1—C2—O2180.000 (1)C2—N1—C10—C11i62.26 (14)
C10—N1—C2—O20.000 (2)C9—N1—C10—C11i117.74 (14)
C9—N1—C2—C30.000 (1)C2—N1—C10—C1162.27 (14)
C10—N1—C2—C3180.000 (1)C9—N1—C10—C11117.73 (14)
O2—C2—C3—C4180.000 (2)N1—C10—C11—C12179.91 (14)
N1—C2—C3—C40.000 (1)C11i—C10—C11—C1254.2 (2)
C2—C3—C4—C5180.000 (2)C10—C11—C12—N1358.25 (19)
C2—C3—C4—C90.000 (1)C11—C12—N13—C12i60.2 (2)
C9—C4—C5—C60.000 (2)C11—C12—N13—C14177.46 (13)
C3—C4—C5—C6180.000 (2)C12—N13—C14—C15i179.93 (15)
C4—C5—C6—C70.000 (2)C12i—N13—C14—C15i59.2 (2)
C5—C6—C7—C80.000 (2)C12—N13—C14—C1559.2 (2)
C6—C7—C8—C90.000 (2)C12i—N13—C14—C15179.93 (15)
C7—C8—C9—C40.000 (2)N13—C14—C15—C16177.74 (14)
C7—C8—C9—N1180.000 (1)C15i—C14—C15—C1654.9 (2)
C5—C4—C9—C80.000 (2)C14—C15—C16—C1756.89 (19)
C3—C4—C9—C8180.000 (1)C15—C16—C17—C16i53.6 (2)
C5—C4—C9—N1180.000 (1)C15—C16—C17—C18178.05 (15)
C3—C4—C9—N10.000 (1)C16—C17—C18—C19i179.53 (17)
C2—N1—C9—C8180.000 (2)C16i—C17—C18—C19i57.4 (2)
C10—N1—C9—C80.000 (2)C16—C17—C18—C1957.4 (2)
C2—N1—C9—C40.000 (1)C16i—C17—C18—C19179.53 (17)
C10—N1—C9—C4180.000 (1)
Symmetry code: (i) x, y, z.
 

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