(5S*,6R*,7R*,9R*)-1-Benzyl-7,9-di­methyl-8-oxo-1-aza­spiro­[4.4]­nonane-6-carbo­nitrile

The racemic title compound, C₁₈H₂₂N₂O, isolated from the reaction of 2-(1-benzyl-2-pyrrolidinyl­idene)­aceto­nitrile, 2,4-di­bromo-3-pentanone and nona­carbonyl­diiron, crystallizes in a centrosymmetric monoclinic space group with four symmetry-equivalent mol­ecules per unit cell. All bond lengths and angles are within expected ranges.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.085
• wR factor = 0.287
• Data-to-parameter ratio = 15.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



DIFMX_01  Alert B The maximum difference density is > 0.1*ZMAX*1.00
          _refine_diff_density_max given =      0.904
          Test value =      0.800


 Alert Level C:



DIFMX_02  Alert C The minimum difference density is > 0.1*ZMAX*0.75
          The relevant atom site should be identified.

RFACR_01  Alert C The value of the weighted R factor is > 0.25
          Weighted R factor given   0.287

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     30
                   C6  -C5  -C9  -N2      4.00  0.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     31
                   C1  -C5  -C9  -N2     16.00  0.00   1.555   1.555   1.555   1.555


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 4 Alert Level C = Please check

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(5S*,6R*,7R*,9R*)-1-Benzyl-7,9-dimethyl-8-oxo-1- azaspiro[4.4]nonane-6-carbonitrile

Crystal data

C18H22N2O	Dx = 1.153 Mg m^−3
Mr = 282.38	Melting point = 381.5–383.5 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.543 (3) Å	Cell parameters from 25 reflections
b = 10.614 (4) Å	θ = 2–12°
c = 14.570 (3) Å	µ = 0.07 mm^−1
β = 93.68 (2)°	T = 295 K
V = 1627.2 (8) Å^3	Rectangular block, colorless
Z = 4	0.8 × 0.6 × 0.5 mm
F(000) = 608

Data collection

Enraf-Nonius CAD-4 diffractometer	θmax = 25.0°, θmin = 2.3°
ω/2θ scans	h = −1→12
6534 measured reflections	k = −12→12
2863 independent reflections	l = −17→17
2336 reflections with I > 2σ(I)	3 standard reflections every 120 min
Rint = 0.067	intensity decay: 3%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.085	w = 1/[σ^2(Fo^2) + (0.1715P)^2 + 0.8378P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.287	(Δ/σ)max = 0.013
S = 1.04	Δρmax = 0.90 e Å^−3
2863 reflections	Δρmin = −0.38 e Å^−3
190 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2164 (2)	0.2828 (2)	0.38453 (16)	0.0485 (6)
C2	0.2704 (3)	0.3378 (3)	0.29658 (18)	0.0592 (7)
H2A	0.2577	0.4282	0.2936	0.071*
H2B	0.3606	0.3202	0.2956	0.071*
C3	0.1978 (4)	0.2734 (4)	0.2175 (2)	0.0822 (10)
H3A	0.1828	0.3309	0.1662	0.099*
H3B	0.2443	0.2009	0.197	0.099*
C4	0.0761 (4)	0.2339 (4)	0.2543 (2)	0.0854 (11)
H4A	0.0145	0.3019	0.2502	0.102*
H4B	0.0408	0.1613	0.2213	0.102*
C5	0.1819 (2)	0.3896 (2)	0.45188 (19)	0.0552 (7)
H5	0.1342	0.3516	0.5004	0.066*
C6	0.3106 (3)	0.4340 (3)	0.4958 (2)	0.0663 (8)
H6	0.3476	0.4932	0.4533	0.08*
C7	0.3884 (3)	0.3150 (3)	0.4977 (2)	0.0705 (9)
C8	0.3166 (3)	0.2121 (3)	0.4469 (2)	0.0662 (8)
H8	0.2701	0.1663	0.4924	0.079*
C9	0.1046 (3)	0.4897 (3)	0.4099 (2)	0.0694 (8)
C10	0.3062 (4)	0.4982 (4)	0.5887 (3)	0.0988 (13)
H10A	0.3903	0.5238	0.61	0.148*
H10B	0.2733	0.4406	0.6321	0.148*
H10C	0.2521	0.5709	0.5829	0.148*
C11	0.3990 (5)	0.1151 (5)	0.4008 (3)	0.1150 (17)
H11A	0.4582	0.0786	0.446	0.172*
H11B	0.4447	0.1557	0.3542	0.172*
H11C	0.3458	0.0502	0.3733	0.172*
C12	0.0052 (3)	0.1803 (4)	0.4063 (3)	0.0825 (10)
H12A	−0.0486	0.2545	0.4051	0.099*
H12B	0.0374	0.1667	0.4694	0.099*
C13	−0.0731 (3)	0.0678 (3)	0.3740 (2)	0.0670 (8)
C14	−0.2073 (4)	0.0809 (3)	0.3622 (3)	0.0822 (10)
H14	−0.2453	0.1578	0.3741	0.099*
C15	−0.2815 (3)	−0.0209 (4)	0.3329 (3)	0.0837 (10)
H15	−0.3696	−0.0136	0.3265	0.1*
C16	−0.2250 (4)	−0.1302 (4)	0.3138 (3)	0.0826 (10)
H16	−0.2754	−0.1977	0.2934	0.099*
C17	−0.0990 (4)	−0.1458 (4)	0.3230 (3)	0.0854 (11)
H17	−0.0625	−0.2227	0.309	0.103*
C18	−0.0257 (3)	−0.0480 (3)	0.3529 (2)	0.0760 (9)
H18	0.0618	−0.0599	0.3596	0.091*
N1	0.1116 (2)	0.2026 (2)	0.34948 (14)	0.0513 (6)
N2	0.0445 (3)	0.5688 (3)	0.3777 (3)	0.1058 (12)
O1	0.4945 (2)	0.3060 (3)	0.5344 (2)	0.1051 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0490 (13)	0.0520 (13)	0.0450 (13)	0.0070 (10)	0.0067 (10)	0.0024 (10)
C2	0.0535 (14)	0.0706 (17)	0.0549 (15)	0.0018 (13)	0.0146 (11)	0.0056 (13)
C3	0.106 (3)	0.095 (2)	0.0472 (15)	−0.022 (2)	0.0118 (16)	0.0103 (15)
C4	0.092 (2)	0.103 (3)	0.0591 (18)	−0.020 (2)	−0.0108 (17)	0.0081 (18)
C5	0.0534 (14)	0.0557 (15)	0.0578 (15)	0.0014 (11)	0.0123 (11)	−0.0030 (12)
C6	0.0645 (17)	0.0719 (18)	0.0627 (16)	−0.0064 (14)	0.0056 (13)	−0.0088 (14)
C7	0.0626 (17)	0.095 (2)	0.0538 (15)	0.0079 (16)	−0.0021 (13)	0.0032 (15)
C8	0.0720 (18)	0.0681 (17)	0.0574 (16)	0.0195 (14)	−0.0038 (14)	0.0039 (13)
C9	0.0622 (17)	0.0617 (17)	0.086 (2)	0.0098 (14)	0.0163 (15)	−0.0060 (15)
C10	0.111 (3)	0.107 (3)	0.078 (2)	−0.013 (2)	0.005 (2)	−0.036 (2)
C11	0.119 (3)	0.109 (3)	0.112 (3)	0.071 (3)	−0.023 (3)	−0.019 (3)
C12	0.077 (2)	0.091 (2)	0.082 (2)	−0.0125 (18)	0.0216 (17)	−0.0146 (18)
C13	0.0784 (19)	0.0647 (17)	0.0604 (16)	−0.0170 (15)	0.0224 (14)	−0.0022 (13)
C14	0.086 (2)	0.0650 (18)	0.097 (3)	0.0084 (17)	0.0178 (19)	0.0006 (17)
C15	0.0594 (18)	0.088 (2)	0.104 (3)	−0.0090 (17)	0.0089 (17)	−0.001 (2)
C16	0.089 (2)	0.078 (2)	0.083 (2)	−0.0117 (19)	0.0256 (18)	0.0053 (18)
C17	0.113 (3)	0.067 (2)	0.079 (2)	0.010 (2)	0.025 (2)	0.0073 (17)
C18	0.076 (2)	0.083 (2)	0.0699 (19)	0.0119 (17)	0.0169 (15)	0.0052 (17)
N1	0.0536 (12)	0.0570 (12)	0.0439 (11)	−0.0008 (9)	0.0076 (9)	0.0052 (9)
N2	0.098 (2)	0.081 (2)	0.140 (3)	0.0355 (19)	0.021 (2)	0.016 (2)
O1	0.0753 (16)	0.141 (3)	0.0951 (19)	0.0097 (16)	−0.0264 (14)	−0.0022 (18)

Geometric parameters (Å, º)

C1—N1	1.461 (3)	C7—C8	1.498 (5)
C1—C8	1.543 (4)	C8—C11	1.529 (5)
C1—C2	1.550 (3)	C9—N2	1.135 (4)
C1—C5	1.558 (3)	C12—N1	1.456 (4)
C2—C3	1.506 (4)	C12—C13	1.510 (5)
C3—C4	1.482 (5)	C13—C18	1.369 (5)
C4—N1	1.452 (4)	C13—C14	1.421 (5)
C5—C9	1.450 (4)	C14—C15	1.386 (5)
C5—C6	1.537 (4)	C15—C16	1.341 (5)
C6—C7	1.505 (5)	C16—C17	1.337 (6)
C6—C10	1.520 (5)	C17—C18	1.350 (5)
C7—O1	1.212 (4)
N1—C1—C8	113.4 (2)	C8—C7—C6	110.2 (2)
N1—C1—C2	103.9 (2)	C7—C8—C11	115.1 (3)
C8—C1—C2	113.3 (2)	C7—C8—C1	104.0 (2)
N1—C1—C5	116.21 (19)	C11—C8—C1	117.1 (3)
C8—C1—C5	99.3 (2)	N2—C9—C5	179.3 (4)
C2—C1—C5	111.1 (2)	N1—C12—C13	112.2 (3)
C3—C2—C1	105.4 (2)	C18—C13—C14	115.9 (3)
C4—C3—C2	105.1 (3)	C18—C13—C12	125.4 (3)
N1—C4—C3	103.6 (3)	C14—C13—C12	118.7 (3)
C9—C5—C6	114.1 (2)	C15—C14—C13	119.9 (3)
C9—C5—C1	114.5 (2)	C16—C15—C14	119.2 (3)
C6—C5—C1	104.4 (2)	C17—C16—C15	122.6 (4)
C7—C6—C10	114.0 (3)	C16—C17—C18	118.7 (4)
C7—C6—C5	102.5 (2)	C17—C18—C13	123.6 (3)
C10—C6—C5	115.6 (3)	C4—N1—C12	114.9 (3)
O1—C7—C8	125.7 (3)	C4—N1—C1	110.1 (2)
O1—C7—C6	124.1 (3)	C12—N1—C1	119.3 (2)
N1—C1—C2—C3	−5.2 (3)	N1—C1—C8—C11	69.4 (4)
C8—C1—C2—C3	118.3 (3)	C2—C1—C8—C11	−48.8 (4)
C5—C1—C2—C3	−130.9 (3)	C5—C1—C8—C11	−166.7 (3)
C1—C2—C3—C4	24.4 (4)	C6—C5—C9—N2	−4E1 (4)
C2—C3—C4—N1	−34.3 (4)	C1—C5—C9—N2	−16E1 (4)
N1—C1—C5—C9	−68.7 (3)	N1—C12—C13—C18	47.9 (5)
C8—C1—C5—C9	169.3 (2)	N1—C12—C13—C14	−130.8 (3)
C2—C1—C5—C9	49.8 (3)	C18—C13—C14—C15	1.3 (5)
N1—C1—C5—C6	165.8 (2)	C12—C13—C14—C15	−179.8 (3)
C8—C1—C5—C6	43.8 (3)	C13—C14—C15—C16	−1.6 (6)
C2—C1—C5—C6	−75.7 (3)	C14—C15—C16—C17	0.8 (6)
C9—C5—C6—C7	−157.8 (2)	C15—C16—C17—C18	0.3 (6)
C1—C5—C6—C7	−32.0 (3)	C16—C17—C18—C13	−0.6 (5)
C9—C5—C6—C10	77.6 (4)	C14—C13—C18—C17	−0.2 (5)
C1—C5—C6—C10	−156.6 (3)	C12—C13—C18—C17	−179.0 (3)
C10—C6—C7—O1	−48.0 (5)	C3—C4—N1—C12	170.3 (3)
C5—C6—C7—O1	−173.6 (3)	C3—C4—N1—C1	32.3 (4)
C10—C6—C7—C8	132.9 (3)	C13—C12—N1—C4	63.3 (4)
C5—C6—C7—C8	7.3 (3)	C13—C12—N1—C1	−162.8 (3)
O1—C7—C8—C11	−29.3 (5)	C8—C1—N1—C4	−140.2 (3)
C6—C7—C8—C11	149.7 (3)	C2—C1—N1—C4	−16.7 (3)
O1—C7—C8—C1	−158.7 (3)	C5—C1—N1—C4	105.6 (3)
C6—C7—C8—C1	20.3 (3)	C8—C1—N1—C12	83.9 (3)
N1—C1—C8—C7	−162.4 (2)	C2—C1—N1—C12	−152.6 (3)
C2—C1—C8—C7	79.5 (3)	C5—C1—N1—C12	−30.3 (3)
C5—C1—C8—C7	−38.4 (3)