1-[1-(Deca­hydro­naphthalen-1-yl)­piperidin-4-yl]­indolin-2-one: one of a novel series of nociceptin receptor ligands:

The title compound, C₂₃H₃₂N₂O, is a member of the family of nociceptin receptor ligands derived from N-(4-piperidinyl)­indolin-2-ones. Modifications of the piperidine N-substituent can produce both agonists and antagonists, the title compound being an agonist with moderate affinity.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.162
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      62.44 Deg.

Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level C
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5750
PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6].....      62.44 Deg.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C20    -   C21     ..       6.59 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C22    -   C23     ..       6.36 su

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2002) and XPREP (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and MidasPlus (Version 2.1; Ferrin et al., 1988); software used to prepare material for publication: SHELXTL.

1-[1-(Decahydronaphthalen-1-yl)piperidin-4-yl]indolin-2-one

Crystal data

C23H32N2O	F(000) = 768
Mr = 352.51	Dx = 1.159 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3559 reflections
a = 8.9714 (2) Å	θ = 3.6–28.3°
b = 8.6150 (2) Å	µ = 0.54 mm^−1
c = 26.4673 (7) Å	T = 293 K
β = 99.155 (2)°	Needle, colourless
V = 2019.56 (8) Å^3	0.21 × 0.08 × 0.04 mm
Z = 4

Data collection

Bruker SMART 6000 CCD diffractometer	3085 independent reflections
Radiation source: rotating anode	2167 reflections with I > 2σ(I)
Göbel optics monochromator	Rint = 0.034
ω scans	θmax = 62.4°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.892, Tmax = 0.978	k = −8→9
10382 measured reflections	l = −28→30

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.162	w = 1/[σ^2(Fo^2) + (0.0929P)^2 + 0.1732P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3085 reflections	Δρmax = 0.17 e Å^−3
236 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0075 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.50614 (18)	0.40193 (19)	0.37532 (6)	0.0609 (5)
O2	0.3519 (2)	0.3838 (2)	0.43626 (6)	0.0986 (6)
C2	0.4777 (3)	0.3873 (3)	0.42467 (8)	0.0703 (6)
C3	0.6269 (3)	0.3791 (3)	0.45974 (9)	0.0810 (7)
H3A	0.6374	0.4639	0.4842	0.097*
H3B	0.6375	0.2815	0.4782	0.097*
C4	0.7401 (3)	0.3919 (2)	0.42459 (9)	0.0680 (6)
C5	0.8939 (3)	0.3936 (3)	0.43366 (12)	0.0876 (8)
H5A	0.9456	0.3829	0.4668	0.105*
C6	0.9728 (3)	0.4115 (3)	0.39298 (15)	0.0993 (10)
H6A	1.0778	0.4120	0.3988	0.119*
C7	0.8954 (3)	0.4284 (3)	0.34411 (13)	0.0920 (8)
H7A	0.9495	0.4415	0.3172	0.110*
C8	0.7397 (3)	0.4265 (2)	0.33378 (9)	0.0715 (6)
H8A	0.6885	0.4376	0.3006	0.086*
C9	0.6626 (2)	0.4073 (2)	0.37461 (8)	0.0605 (5)
C10	0.3839 (2)	0.4136 (2)	0.33192 (7)	0.0605 (6)
H10A	0.2899	0.3995	0.3458	0.073*
C11	0.3871 (2)	0.2862 (2)	0.29255 (8)	0.0697 (6)
H11A	0.3823	0.1855	0.3087	0.084*
H11B	0.4807	0.2916	0.2786	0.084*
C12	0.2533 (2)	0.3049 (2)	0.24957 (8)	0.0705 (6)
H12A	0.2577	0.2259	0.2237	0.085*
H12B	0.1599	0.2913	0.2631	0.085*
N13	0.25526 (19)	0.45793 (19)	0.22645 (6)	0.0621 (5)
C14	0.2419 (3)	0.5789 (2)	0.26350 (8)	0.0674 (6)
H14A	0.1482	0.5658	0.2769	0.081*
H14B	0.2393	0.6795	0.2469	0.081*
C15	0.3738 (2)	0.5730 (2)	0.30705 (8)	0.0671 (6)
H15A	0.3607	0.6514	0.3323	0.080*
H15B	0.4668	0.5952	0.2941	0.080*
C16	0.1476 (2)	0.4759 (3)	0.17804 (8)	0.0704 (6)
H16A	0.1470	0.5868	0.1697	0.084*
C17	0.2026 (3)	0.3935 (2)	0.13379 (8)	0.0695 (6)
H17A	0.2003	0.2818	0.1407	0.083*
C18	0.3641 (3)	0.4350 (3)	0.12785 (9)	0.0793 (7)
H18A	0.3713	0.5467	0.1241	0.095*
H18B	0.4311	0.4054	0.1588	0.095*
C19	0.4166 (4)	0.3577 (3)	0.08264 (9)	0.1025 (9)
H19A	0.5167	0.3952	0.0796	0.123*
H19B	0.4231	0.2465	0.0884	0.123*
C20	0.3109 (4)	0.3899 (3)	0.03359 (10)	0.1064 (10)
H20A	0.3428	0.3312	0.0059	0.128*
H20B	0.3148	0.4993	0.0253	0.128*
C21	0.1513 (4)	0.3457 (3)	0.03866 (10)	0.1071 (11)
H21A	0.1461	0.2340	0.0427	0.129*
H21B	0.0850	0.3734	0.0073	0.129*
C22	0.0949 (3)	0.4235 (3)	0.08346 (9)	0.0825 (8)
H22A	0.0966	0.5356	0.0772	0.099*
C23	−0.0670 (4)	0.3817 (3)	0.08823 (12)	0.1087 (11)
H23A	−0.1326	0.4085	0.0567	0.130*
H23B	−0.0741	0.2706	0.0932	0.130*
C24	−0.1208 (3)	0.4648 (4)	0.13228 (13)	0.1148 (11)
H24A	−0.2215	0.4295	0.1354	0.138*
H24B	−0.1255	0.5755	0.1255	0.138*
C25	−0.0151 (3)	0.4344 (3)	0.18209 (11)	0.0927 (8)
H25A	−0.0205	0.3255	0.1910	0.111*
H25B	−0.0476	0.4951	0.2092	0.111*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0529 (11)	0.0810 (12)	0.0483 (10)	0.0014 (8)	0.0065 (8)	0.0028 (8)
O2	0.0771 (13)	0.1566 (18)	0.0663 (11)	−0.0020 (10)	0.0239 (9)	0.0072 (10)
C2	0.0676 (16)	0.0899 (16)	0.0540 (13)	0.0010 (11)	0.0119 (11)	0.0019 (11)
C3	0.0840 (18)	0.0957 (18)	0.0585 (14)	0.0049 (13)	−0.0036 (12)	0.0009 (12)
C4	0.0618 (15)	0.0627 (13)	0.0749 (15)	0.0072 (10)	−0.0036 (12)	−0.0069 (11)
C5	0.0707 (18)	0.0762 (16)	0.105 (2)	0.0097 (12)	−0.0197 (16)	−0.0122 (14)
C6	0.0562 (16)	0.0863 (19)	0.153 (3)	0.0026 (12)	0.0093 (19)	−0.0224 (18)
C7	0.0706 (19)	0.0827 (17)	0.128 (3)	−0.0050 (12)	0.0337 (17)	−0.0148 (16)
C8	0.0642 (16)	0.0699 (14)	0.0827 (16)	−0.0015 (10)	0.0186 (12)	−0.0063 (11)
C9	0.0536 (13)	0.0600 (13)	0.0667 (14)	0.0029 (9)	0.0063 (10)	−0.0036 (10)
C10	0.0529 (13)	0.0751 (14)	0.0522 (12)	0.0009 (9)	0.0045 (9)	0.0024 (10)
C11	0.0766 (15)	0.0623 (13)	0.0645 (13)	0.0036 (10)	−0.0058 (11)	0.0008 (11)
C12	0.0736 (15)	0.0610 (13)	0.0704 (14)	0.0013 (10)	−0.0080 (11)	−0.0017 (11)
N13	0.0647 (11)	0.0596 (10)	0.0576 (10)	0.0017 (8)	−0.0040 (8)	0.0043 (8)
C14	0.0688 (14)	0.0638 (13)	0.0682 (14)	0.0032 (10)	0.0062 (11)	0.0024 (11)
C15	0.0702 (15)	0.0652 (13)	0.0635 (13)	0.0041 (10)	0.0036 (11)	−0.0038 (10)
C16	0.0693 (15)	0.0686 (14)	0.0666 (14)	−0.0009 (10)	−0.0097 (11)	0.0092 (11)
C17	0.0824 (17)	0.0584 (13)	0.0585 (14)	−0.0020 (10)	−0.0166 (11)	0.0023 (10)
C18	0.0869 (18)	0.0880 (16)	0.0576 (14)	0.0003 (13)	−0.0055 (12)	−0.0039 (12)
C19	0.121 (2)	0.118 (2)	0.0635 (17)	0.0166 (17)	0.0004 (15)	−0.0059 (15)
C20	0.146 (3)	0.108 (2)	0.0594 (17)	0.0114 (19)	−0.0030 (17)	−0.0121 (14)
C21	0.156 (3)	0.0800 (18)	0.0666 (17)	0.0029 (17)	−0.0410 (17)	0.0009 (14)
C22	0.094 (2)	0.0705 (15)	0.0695 (16)	−0.0082 (12)	−0.0293 (13)	0.0069 (12)
C23	0.104 (2)	0.101 (2)	0.100 (2)	−0.0165 (16)	−0.0478 (18)	0.0183 (17)
C24	0.0729 (19)	0.132 (3)	0.125 (3)	−0.0091 (16)	−0.0287 (17)	0.022 (2)
C25	0.0648 (16)	0.1062 (19)	0.100 (2)	−0.0045 (13)	−0.0097 (14)	0.0153 (15)

Geometric parameters (Å, º)

N1—C2	1.376 (3)	C14—H14B	0.9700
N1—C9	1.408 (3)	C15—H15A	0.9700
N1—C10	1.460 (2)	C15—H15B	0.9700
O2—C2	1.216 (3)	C16—C17	1.518 (3)
C2—C3	1.505 (3)	C16—C25	1.523 (3)
C3—C4	1.486 (3)	C16—H16A	0.9800
C3—H3A	0.9700	C17—C18	1.525 (3)
C3—H3B	0.9700	C17—C22	1.538 (3)
C4—C5	1.363 (3)	C17—H17A	0.9800
C4—C9	1.399 (3)	C18—C19	1.509 (3)
C5—C6	1.388 (4)	C18—H18A	0.9700
C5—H5A	0.9300	C18—H18B	0.9700
C6—C7	1.375 (4)	C19—C20	1.507 (4)
C6—H6A	0.9300	C19—H19A	0.9700
C7—C8	1.380 (3)	C19—H19B	0.9700
C7—H7A	0.9300	C20—C21	1.508 (4)
C8—C9	1.382 (3)	C20—H20A	0.9700
C8—H8A	0.9300	C20—H20B	0.9700
C10—C11	1.517 (3)	C21—C22	1.517 (4)
C10—C15	1.520 (3)	C21—H21A	0.9700
C10—H10A	0.9800	C21—H21B	0.9700
C11—C12	1.526 (3)	C22—C23	1.522 (4)
C11—H11A	0.9700	C22—H22A	0.9800
C11—H11B	0.9700	C23—C24	1.511 (4)
C12—N13	1.454 (3)	C23—H23A	0.9700
C12—H12A	0.9700	C23—H23B	0.9700
C12—H12B	0.9700	C24—C25	1.519 (3)
N13—C14	1.449 (2)	C24—H24A	0.9700
N13—C16	1.485 (2)	C24—H24B	0.9700
C14—C15	1.515 (3)	C25—H25A	0.9700
C14—H14A	0.9700	C25—H25B	0.9700
C2—N1—C9	110.60 (17)	H15A—C15—H15B	108.1
C2—N1—C10	121.59 (17)	N13—C16—C17	111.74 (17)
C9—N1—C10	127.79 (16)	N13—C16—C25	114.44 (19)
O2—C2—N1	124.2 (2)	C17—C16—C25	112.16 (19)
O2—C2—C3	127.9 (2)	N13—C16—H16A	105.9
N1—C2—C3	108.0 (2)	C17—C16—H16A	105.9
C4—C3—C2	103.89 (19)	C25—C16—H16A	105.9
C4—C3—H3A	111.0	C16—C17—C18	113.61 (17)
C2—C3—H3A	111.0	C16—C17—C22	110.68 (19)
C4—C3—H3B	111.0	C18—C17—C22	110.31 (19)
C2—C3—H3B	111.0	C16—C17—H17A	107.3
H3A—C3—H3B	109.0	C18—C17—H17A	107.3
C5—C4—C9	120.1 (2)	C22—C17—H17A	107.3
C5—C4—C3	131.6 (2)	C19—C18—C17	113.6 (2)
C9—C4—C3	108.23 (19)	C19—C18—H18A	108.8
C4—C5—C6	119.5 (3)	C17—C18—H18A	108.8
C4—C5—H5A	120.3	C19—C18—H18B	108.8
C6—C5—H5A	120.3	C17—C18—H18B	108.8
C7—C6—C5	119.8 (3)	H18A—C18—H18B	107.7
C7—C6—H6A	120.1	C20—C19—C18	111.7 (2)
C5—C6—H6A	120.1	C20—C19—H19A	109.3
C6—C7—C8	121.9 (3)	C18—C19—H19A	109.3
C6—C7—H7A	119.0	C20—C19—H19B	109.3
C8—C7—H7A	119.0	C18—C19—H19B	109.3
C7—C8—C9	117.6 (2)	H19A—C19—H19B	107.9
C7—C8—H8A	121.2	C19—C20—C21	110.7 (2)
C9—C8—H8A	121.2	C19—C20—H20A	109.5
C8—C9—C4	121.0 (2)	C21—C20—H20A	109.5
C8—C9—N1	129.7 (2)	C19—C20—H20B	109.5
C4—C9—N1	109.30 (19)	C21—C20—H20B	109.5
N1—C10—C11	113.38 (16)	H20A—C20—H20B	108.1
N1—C10—C15	112.90 (16)	C20—C21—C22	113.4 (2)
C11—C10—C15	111.28 (17)	C20—C21—H21A	108.9
N1—C10—H10A	106.2	C22—C21—H21A	108.9
C11—C10—H10A	106.2	C20—C21—H21B	108.9
C15—C10—H10A	106.2	C22—C21—H21B	108.9
C10—C11—C12	109.69 (16)	H21A—C21—H21B	107.7
C10—C11—H11A	109.7	C21—C22—C23	113.7 (2)
C12—C11—H11A	109.7	C21—C22—C17	111.2 (2)
C10—C11—H11B	109.7	C23—C22—C17	111.4 (2)
C12—C11—H11B	109.7	C21—C22—H22A	106.7
H11A—C11—H11B	108.2	C23—C22—H22A	106.7
N13—C12—C11	110.41 (16)	C17—C22—H22A	106.7
N13—C12—H12A	109.6	C24—C23—C22	112.2 (2)
C11—C12—H12A	109.6	C24—C23—H23A	109.2
N13—C12—H12B	109.6	C22—C23—H23A	109.2
C11—C12—H12B	109.6	C24—C23—H23B	109.2
H12A—C12—H12B	108.1	C22—C23—H23B	109.2
C14—N13—C12	111.07 (16)	H23A—C23—H23B	107.9
C14—N13—C16	113.36 (16)	C23—C24—C25	110.9 (2)
C12—N13—C16	114.05 (15)	C23—C24—H24A	109.5
N13—C14—C15	110.61 (17)	C25—C24—H24A	109.5
N13—C14—H14A	109.5	C23—C24—H24B	109.5
C15—C14—H14A	109.5	C25—C24—H24B	109.5
N13—C14—H14B	109.5	H24A—C24—H24B	108.1
C15—C14—H14B	109.5	C24—C25—C16	111.8 (2)
H14A—C14—H14B	108.1	C24—C25—H25A	109.3
C14—C15—C10	110.22 (16)	C16—C25—H25A	109.3
C14—C15—H15A	109.6	C24—C25—H25B	109.3
C10—C15—H15A	109.6	C16—C25—H25B	109.3
C14—C15—H15B	109.6	H25A—C25—H25B	107.9
C10—C15—H15B	109.6
C9—N1—C2—O2	178.1 (2)	C11—C12—N13—C16	168.65 (18)
C10—N1—C2—O2	−0.4 (3)	C12—N13—C14—C15	61.5 (2)
C9—N1—C2—C3	−1.2 (2)	C16—N13—C14—C15	−168.53 (17)
C10—N1—C2—C3	−179.71 (17)	N13—C14—C15—C10	−56.5 (2)
O2—C2—C3—C4	−178.9 (2)	N1—C10—C15—C14	−178.16 (17)
N1—C2—C3—C4	0.4 (2)	C11—C10—C15—C14	53.0 (2)
C2—C3—C4—C5	179.1 (2)	C14—N13—C16—C17	156.84 (18)
C2—C3—C4—C9	0.5 (2)	C12—N13—C16—C17	−74.7 (2)
C9—C4—C5—C6	0.3 (3)	C14—N13—C16—C25	−74.3 (2)
C3—C4—C5—C6	−178.2 (2)	C12—N13—C16—C25	54.1 (3)
C4—C5—C6—C7	0.5 (4)	N13—C16—C17—C18	−51.2 (2)
C5—C6—C7—C8	−0.8 (4)	C25—C16—C17—C18	178.75 (18)
C6—C7—C8—C9	0.2 (3)	N13—C16—C17—C22	−175.95 (17)
C7—C8—C9—C4	0.5 (3)	C25—C16—C17—C22	54.0 (2)
C7—C8—C9—N1	179.58 (19)	C16—C17—C18—C19	−177.79 (19)
C5—C4—C9—C8	−0.8 (3)	C22—C17—C18—C19	−52.8 (3)
C3—C4—C9—C8	177.96 (19)	C17—C18—C19—C20	54.6 (3)
C5—C4—C9—N1	179.98 (17)	C18—C19—C20—C21	−54.1 (3)
C3—C4—C9—N1	−1.2 (2)	C19—C20—C21—C22	55.2 (3)
C2—N1—C9—C8	−177.6 (2)	C20—C21—C22—C23	179.0 (2)
C10—N1—C9—C8	0.9 (3)	C20—C21—C22—C17	−54.4 (3)
C2—N1—C9—C4	1.6 (2)	C16—C17—C22—C21	178.3 (2)
C10—N1—C9—C4	179.97 (17)	C18—C17—C22—C21	51.7 (3)
C2—N1—C10—C11	−121.2 (2)	C16—C17—C22—C23	−53.8 (3)
C9—N1—C10—C11	60.6 (3)	C18—C17—C22—C23	179.6 (2)
C2—N1—C10—C15	111.1 (2)	C21—C22—C23—C24	−178.4 (2)
C9—N1—C10—C15	−67.1 (2)	C17—C22—C23—C24	55.1 (3)
N1—C10—C11—C12	178.36 (17)	C22—C23—C24—C25	−55.2 (3)
C15—C10—C11—C12	−53.1 (2)	C23—C24—C25—C16	54.6 (3)
C10—C11—C12—N13	56.9 (2)	N13—C16—C25—C24	176.4 (2)
C11—C12—N13—C14	−61.8 (2)	C17—C16—C25—C24	−54.9 (3)