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The title compound, C21H30N2O, 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 partial agonist with high affinity. The cyclo­octyl ring is disordered over two positions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804016903/dn6152sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804016903/dn6152Isup2.hkl
Contains datablock I

CCDC reference: 251734

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.048
  • wR factor = 0.135
  • Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C22A
Alert level C THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5753 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 62.49 Deg. PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.80 Sigma PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT128_ALERT_4_C Non-standard setting of Space group Pc .... Pn PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C12 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C20A PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C19B PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N13 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C16A PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C21A PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C17B PLAT301_ALERT_3_C Main Residue Disorder ......................... 25.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 3.00 Deg. C16B -N13 -C16A 1.555 1.555 1.555
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 62.49 From the CIF: _reflns_number_total 2411 Count of symmetry unique reflns 1519 Completeness (_total/calc) 158.72% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 892 Fraction of Friedel pairs measured 0.587 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 2002) and XPREP (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
C21H30N2OF(000) = 356
Mr = 326.47Dx = 1.144 Mg m3
Monoclinic, PnCu Kα radiation, λ = 1.54178 Å
Hall symbol: P -2yacCell parameters from 1838 reflections
a = 5.9170 (2) Åθ = 2.7–53.4°
b = 16.5865 (6) ŵ = 0.54 mm1
c = 9.9576 (4) ÅT = 293 K
β = 104.128 (2)°Plate, colourless
V = 947.70 (6) Å30.54 × 0.16 × 0.02 mm
Z = 2
Data collection top
Bruker SMART 6000 CCD
diffractometer
2411 independent reflections
Radiation source: rotating anode1979 reflections with I > 2σ(I)
Göbel optics monochromatorRint = 0.026
ω scansθmax = 62.5°, θmin = 5.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 65
Tmin = 0.747, Tmax = 0.989k = 1818
4915 measured reflectionsl = 1011
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)] = 0.048H-atom parameters constrained
wR(F2) = 0.135 w = 1/[σ2(Fo2) + (0.0913P)2 + 0.0168P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.025
2411 reflectionsΔρmax = 0.16 e Å3
290 parametersΔρmin = 0.14 e Å3
165 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0028 (10)
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. The populations were initially refined, then set at 70:30 for the final refinements. The bond lengths, angles, and anisotropic thermal parameters of the atoms of the cyclooctyl ring were constrained to help stabilize the refinement of the disordered group. 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)
N10.3987 (4)0.05839 (17)0.0457 (3)0.0738 (7)
O20.6230 (4)0.04010 (16)0.1115 (3)0.1052 (8)
C20.5251 (6)0.0838 (2)0.0440 (3)0.0836 (9)
C30.5221 (7)0.1746 (2)0.0447 (4)0.0899 (10)
H3A0.46170.19520.13780.108*
H3B0.67730.19610.00800.108*
C40.3651 (6)0.1958 (2)0.0461 (3)0.0788 (9)
C50.2830 (9)0.2680 (2)0.0818 (5)0.1048 (12)
H50.32360.31610.04580.126*
C60.1393 (9)0.2681 (3)0.1721 (5)0.1140 (13)
H60.08610.31690.19870.137*
C70.0738 (7)0.1975 (2)0.2231 (4)0.0953 (11)
H70.02330.19900.28380.114*
C80.1494 (6)0.1243 (2)0.1860 (3)0.0790 (9)
H80.10290.07630.21940.095*
C90.2969 (5)0.12414 (18)0.0974 (3)0.0714 (8)
C100.3559 (6)0.02525 (19)0.0775 (3)0.0759 (9)
H100.29680.02440.16120.091*
C110.1727 (6)0.0660 (2)0.0333 (4)0.0927 (10)
H11A0.22400.06810.11860.111*
H11B0.02940.03500.05060.111*
C120.1278 (6)0.1500 (2)0.0101 (5)0.1033 (13)
H12A0.01170.17550.06340.124*
H12B0.06610.14740.09170.124*
C140.5136 (7)0.1604 (2)0.1492 (4)0.1033 (12)
H14A0.45680.15760.23260.124*
H14B0.65310.19340.16920.124*
C150.5741 (7)0.0767 (2)0.1102 (4)0.0999 (12)
H15A0.68940.05300.18630.120*
H15B0.63980.07930.03010.120*
N130.3383 (4)0.19810 (16)0.0402 (3)0.0794 (7)
C16A0.305 (4)0.2856 (5)0.0623 (15)0.087 (4)0.55
H16A0.46070.30770.10080.105*0.55
C17A0.167 (3)0.3023 (7)0.1694 (14)0.130 (4)0.55
H17A0.18780.25700.23280.156*0.55
H17B0.00310.30460.12230.156*0.55
C18A0.230 (3)0.3801 (5)0.2554 (12)0.151 (4)0.55
H18A0.19250.37430.34460.181*0.55
H18B0.39460.39170.27080.181*0.55
C19A0.085 (3)0.4474 (8)0.1722 (16)0.168 (5)0.55
H19A0.07510.42940.15440.202*0.55
H19B0.09860.49260.23560.202*0.55
C20A0.108 (3)0.4785 (9)0.0550 (16)0.196 (5)0.55
H20A0.08900.53590.06760.235*0.55
H20B0.03370.46170.01090.235*0.55
C21A0.269 (3)0.4752 (8)0.0182 (17)0.173 (5)0.55
H21A0.42050.47700.04650.208*0.55
H21B0.25400.52360.07430.208*0.55
C22A0.266 (3)0.4074 (7)0.1078 (14)0.188 (5)0.55
H22A0.15410.41970.19420.226*0.55
H22B0.41780.40530.12830.226*0.55
C23A0.2148 (19)0.3275 (4)0.0693 (8)0.128 (3)0.55
H23A0.25230.29260.13900.154*0.55
H23B0.04660.32570.08470.154*0.55
C16B0.296 (5)0.2831 (7)0.066 (2)0.102 (6)0.45
H16B0.15090.29750.00120.123*0.45
C17B0.257 (3)0.3024 (10)0.2061 (16)0.122 (5)0.45
H17C0.40570.31790.26630.146*0.45
H17D0.20760.25340.24390.146*0.45
C18B0.082 (4)0.3681 (9)0.213 (3)0.179 (6)0.45
H18C0.04540.36520.13000.215*0.45
H18D0.01720.35840.29190.215*0.45
C19B0.182 (5)0.4493 (11)0.223 (3)0.216 (8)0.45
H19C0.05140.48450.22460.260*0.45
H19D0.28170.45150.31640.260*0.45
C20B0.298 (5)0.4879 (12)0.149 (3)0.212 (7)0.45
H20C0.19860.53390.11570.254*0.45
H20D0.42840.50980.21780.254*0.45
C21B0.387 (4)0.4740 (10)0.049 (2)0.184 (6)0.45
H21C0.54790.49030.08650.221*0.45
H21D0.32070.51660.01530.221*0.45
C22B0.413 (3)0.4106 (8)0.0423 (18)0.159 (5)0.45
H22C0.53110.42550.09020.191*0.45
H22D0.26710.40360.11140.191*0.45
C23B0.479 (2)0.3326 (6)0.0306 (13)0.127 (3)0.45
H23C0.55540.30010.02640.153*0.45
H23D0.59470.34410.11590.153*0.45
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0763 (16)0.0810 (16)0.0696 (15)0.0068 (13)0.0283 (13)0.0015 (12)
O20.1087 (18)0.1284 (19)0.0922 (16)0.0064 (16)0.0511 (15)0.0144 (15)
C20.079 (2)0.107 (3)0.0674 (18)0.003 (2)0.0246 (16)0.0043 (19)
C30.093 (2)0.102 (3)0.077 (2)0.009 (2)0.0259 (17)0.0054 (19)
C40.089 (2)0.084 (2)0.065 (2)0.0096 (18)0.0215 (16)0.0004 (16)
C50.137 (3)0.075 (2)0.106 (3)0.000 (2)0.037 (3)0.003 (2)
C60.154 (4)0.091 (3)0.107 (3)0.021 (3)0.051 (3)0.007 (2)
C70.112 (3)0.092 (3)0.091 (2)0.020 (2)0.043 (2)0.0017 (18)
C80.091 (2)0.082 (2)0.070 (2)0.0064 (17)0.0300 (16)0.0054 (16)
C90.0732 (18)0.0757 (19)0.0649 (19)0.0087 (16)0.0164 (14)0.0017 (14)
C100.087 (2)0.0810 (19)0.0659 (18)0.0168 (16)0.0305 (17)0.0043 (14)
C110.0649 (19)0.095 (2)0.114 (3)0.0038 (17)0.0139 (18)0.0261 (19)
C120.069 (2)0.103 (3)0.136 (3)0.0012 (19)0.022 (2)0.031 (2)
C140.109 (3)0.091 (2)0.097 (3)0.027 (2)0.000 (2)0.004 (2)
C150.088 (2)0.093 (3)0.102 (3)0.0154 (18)0.0102 (19)0.0150 (19)
N130.0768 (17)0.0854 (17)0.0794 (17)0.0037 (14)0.0260 (13)0.0002 (14)
C16A0.107 (9)0.074 (8)0.098 (7)0.002 (7)0.056 (7)0.011 (6)
C17A0.197 (12)0.090 (6)0.140 (9)0.015 (7)0.112 (8)0.024 (5)
C18A0.229 (12)0.098 (6)0.145 (9)0.010 (6)0.086 (8)0.040 (5)
C19A0.217 (11)0.149 (9)0.170 (9)0.046 (8)0.108 (9)0.032 (6)
C20A0.251 (12)0.164 (9)0.190 (10)0.098 (9)0.089 (9)0.020 (8)
C21A0.246 (13)0.111 (7)0.180 (10)0.030 (9)0.085 (9)0.010 (6)
C22A0.286 (14)0.134 (7)0.146 (9)0.009 (9)0.056 (10)0.011 (6)
C23A0.181 (8)0.092 (4)0.106 (5)0.045 (5)0.025 (5)0.001 (4)
C16B0.107 (11)0.099 (12)0.104 (9)0.016 (9)0.029 (9)0.031 (9)
C17B0.130 (9)0.134 (10)0.110 (8)0.025 (7)0.045 (7)0.027 (7)
C18B0.194 (12)0.172 (12)0.192 (12)0.000 (9)0.090 (11)0.031 (11)
C19B0.280 (17)0.168 (14)0.206 (15)0.026 (12)0.069 (13)0.035 (13)
C20B0.264 (16)0.149 (11)0.224 (16)0.055 (11)0.063 (11)0.052 (11)
C21B0.206 (13)0.109 (9)0.254 (17)0.060 (9)0.088 (12)0.009 (10)
C22B0.178 (11)0.109 (7)0.203 (13)0.023 (8)0.070 (10)0.044 (8)
C23B0.148 (8)0.103 (6)0.152 (8)0.004 (6)0.078 (7)0.007 (6)
Geometric parameters (Å, º) top
N1—C21.365 (4)C18A—C19A1.523 (14)
N1—C91.403 (4)C18A—H18A0.9700
N1—C101.459 (4)C18A—H18B0.9700
O2—C21.226 (4)C19A—C20A1.311 (12)
C2—C31.506 (5)C19A—H19A0.9700
C3—C41.488 (5)C19A—H19B0.9700
C3—H3A0.9700C20A—C21A1.333 (13)
C3—H3B0.9700C20A—H20A0.9700
C4—C51.373 (5)C20A—H20B0.9700
C4—C91.391 (4)C21A—C22A1.433 (12)
C5—C61.379 (6)C21A—H21A0.9700
C5—H50.9300C21A—H21B0.9700
C6—C71.371 (5)C22A—C23A1.432 (11)
C6—H60.9300C22A—H22A0.9700
C7—C81.375 (4)C22A—H22B0.9700
C7—H70.9300C23A—H23A0.9700
C8—C91.384 (4)C23A—H23B0.9700
C8—H80.9300C16B—C23B1.471 (17)
C10—C111.505 (5)C16B—C17B1.504 (15)
C10—C151.516 (5)C16B—H16B0.9800
C10—H100.9800C17B—C18B1.518 (15)
C11—C121.501 (5)C17B—H17C0.9700
C11—H11A0.9700C17B—H17D0.9700
C11—H11B0.9700C18B—C19B1.465 (16)
C12—N131.448 (4)C18B—H18C0.9700
C12—H12A0.9700C18B—H18D0.9700
C12—H12B0.9700C19B—C20B1.300 (15)
C14—N131.447 (5)C19B—H19C0.9700
C14—C151.508 (6)C19B—H19D0.9700
C14—H14A0.9700C20B—C21B1.253 (14)
C14—H14B0.9700C20B—H20C0.9700
C15—H15A0.9700C20B—H20D0.9700
C15—H15B0.9700C21B—C22B1.423 (14)
N13—C16B1.465 (12)C21B—H21C0.9700
N13—C16A1.489 (9)C21B—H21D0.9700
C16A—C23A1.464 (15)C22B—C23B1.488 (13)
C16A—C17A1.516 (11)C22B—H22C0.9700
C16A—H16A0.9800C22B—H22D0.9700
C17A—C18A1.543 (12)C23B—H23C0.9700
C17A—H17A0.9700C23B—H23D0.9700
C17A—H17B0.9700
C2—N1—C9110.7 (3)C19A—C18A—H18B110.4
C2—N1—C10126.0 (3)C17A—C18A—H18B110.4
C9—N1—C10123.2 (2)H18A—C18A—H18B108.6
O2—C2—N1125.7 (3)C20A—C19A—C18A127.5 (10)
O2—C2—C3126.5 (3)C20A—C19A—H19A105.4
N1—C2—C3107.7 (3)C18A—C19A—H19A105.4
C4—C3—C2104.0 (3)C20A—C19A—H19B105.4
C4—C3—H3A111.0C18A—C19A—H19B105.4
C2—C3—H3A111.0H19A—C19A—H19B106.0
C4—C3—H3B111.0C19A—C20A—C21A135.2 (14)
C2—C3—H3B111.0C19A—C20A—H20A103.4
H3A—C3—H3B109.0C21A—C20A—H20A103.4
C5—C4—C9119.9 (3)C19A—C20A—H20B103.4
C5—C4—C3132.6 (3)C21A—C20A—H20B103.4
C9—C4—C3107.6 (3)H20A—C20A—H20B105.2
C4—C5—C6118.9 (4)C20A—C21A—C22A118.2 (15)
C4—C5—H5120.6C20A—C21A—H21A107.8
C6—C5—H5120.6C22A—C21A—H21A107.8
C7—C6—C5121.1 (4)C20A—C21A—H21B107.8
C7—C6—H6119.5C22A—C21A—H21B107.8
C5—C6—H6119.5H21A—C21A—H21B107.1
C6—C7—C8121.0 (3)C23A—C22A—C21A122.0 (11)
C6—C7—H7119.5C23A—C22A—H22A106.8
C8—C7—H7119.5C21A—C22A—H22A106.8
C7—C8—C9118.0 (3)C23A—C22A—H22B106.8
C7—C8—H8121.0C21A—C22A—H22B106.8
C9—C8—H8121.0H22A—C22A—H22B106.7
C8—C9—C4121.1 (3)C22A—C23A—C16A128.7 (10)
C8—C9—N1129.0 (3)C22A—C23A—H23A105.1
C4—C9—N1109.9 (2)C16A—C23A—H23A105.1
N1—C10—C11113.6 (3)C22A—C23A—H23B105.1
N1—C10—C15113.5 (3)C16A—C23A—H23B105.1
C11—C10—C15109.2 (3)H23A—C23A—H23B105.9
N1—C10—H10106.7N13—C16B—C23B109.2 (12)
C11—C10—H10106.7N13—C16B—C17B116.0 (12)
C15—C10—H10106.7C23B—C16B—C17B113.0 (15)
C12—C11—C10110.6 (3)N13—C16B—H16B105.9
C12—C11—H11A109.5C23B—C16B—H16B105.9
C10—C11—H11A109.5C17B—C16B—H16B105.9
C12—C11—H11B109.5C16B—C17B—C18B117.0 (17)
C10—C11—H11B109.5C16B—C17B—H17C108.1
H11A—C11—H11B108.1C18B—C17B—H17C108.0
N13—C12—C11111.6 (3)C16B—C17B—H17D108.1
N13—C12—H12A109.3C18B—C17B—H17D108.1
C11—C12—H12A109.3H17C—C17B—H17D107.3
N13—C12—H12B109.3C19B—C18B—C17B113.2 (17)
C11—C12—H12B109.3C19B—C18B—H18C108.9
H12A—C12—H12B108.0C17B—C18B—H18C108.9
N13—C14—C15112.1 (3)C19B—C18B—H18D108.9
N13—C14—H14A109.2C17B—C18B—H18D108.9
C15—C14—H14A109.2H18C—C18B—H18D107.8
N13—C14—H14B109.2C20B—C19B—C18B132 (2)
C15—C14—H14B109.2C20B—C19B—H19C104.2
H14A—C14—H14B107.9C18B—C19B—H19C104.2
C14—C15—C10109.3 (3)C20B—C19B—H19D104.2
C14—C15—H15A109.8C18B—C19B—H19D104.2
C10—C15—H15A109.8H19C—C19B—H19D105.5
C14—C15—H15B109.8C21B—C20B—C19B138.4 (19)
C10—C15—H15B109.8C21B—C20B—H20C102.5
H15A—C15—H15B108.3C19B—C20B—H20C102.5
C14—N13—C12109.9 (3)C21B—C20B—H20D102.5
C14—N13—C16B114.0 (11)C19B—C20B—H20D102.5
C12—N13—C16B113.0 (10)H20C—C20B—H20D104.9
C14—N13—C16A114.0 (8)C20B—C21B—C22B140.6 (16)
C12—N13—C16A115.4 (8)C20B—C21B—H21C101.9
C16B—N13—C16A3.0 (11)C22B—C21B—H21C101.9
C23A—C16A—N13111.2 (10)C20B—C21B—H21D101.9
C23A—C16A—C17A113.8 (13)C22B—C21B—H21D101.9
N13—C16A—C17A113.3 (7)H21C—C21B—H21D104.7
C23A—C16A—H16A105.9C21B—C22B—C23B112.8 (13)
N13—C16A—H16A105.9C21B—C22B—H22C109.0
C17A—C16A—H16A105.9C23B—C22B—H22C109.0
C16A—C17A—C18A116.5 (12)C21B—C22B—H22D109.0
C16A—C17A—H17A108.2C23B—C22B—H22D109.0
C18A—C17A—H17A108.2H22C—C22B—H22D107.8
C16A—C17A—H17B108.2C16B—C23B—C22B118.7 (13)
C18A—C17A—H17B108.2C16B—C23B—H23C107.6
H17A—C17A—H17B107.3C22B—C23B—H23C107.6
C19A—C18A—C17A106.5 (12)C16B—C23B—H23D107.6
C19A—C18A—H18A110.4C22B—C23B—H23D107.6
C17A—C18A—H18A110.4H23C—C23B—H23D107.1
 

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