rac-Diethyl 9-hy­droxy-9-methyl-7-phenyl-1,4-diaza­spiro­[4.5]decane-6,8-dicarboxyl­ate

Maharramov, A.M.; Ismiyev, A.I.; Rashidov, B.A.; Rahimova, G.M.; Allahverdiyev, M.A.

doi:10.1107/S1600536810054498

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o291

doi:10.1107/S1600536810054498

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rac-Diethyl 9-hydroxy-9-methyl-7-phenyl-1,4-diazaspiro[4.5]decane-6,8-dicarboxylate

Abel M. Maharramov,^a Arif I. Ismiyev,^a Bahruz A. Rashidov,^a ^* Gunel M. Rahimova ^a and Mirza A. Allahverdiyev ^a

^aBaku State University, Z. Khalilov St. 23, Baku, AZ-1148, Azerbaijan
^*Correspondence e-mail: bahruz_81@mail.ru

(Received 19 December 2010; accepted 28 December 2010; online 8 January 2011)

The title molecule, C₂₁H₃₀N₂O₅, is chiral with four stereogenic centres. The crystal is a racemate and consists of enantiomeric pairs with the relative configuration rac-(6S*,7R*,8R*,9S*). The ethyl fragment of the ethoxycarbonyl group at position 6 is disordered in a 0.46 (3):0.54 (3) ratio. The crystal structure features intermolecular N—H⋯O. Intramolecular O—H⋯N and N—H⋯O hydrogen bonds also occur.

Related literature

For general background to the biological activity of β-cycloketoles and their nitrogenous derivatives, see: Krivenko et al. (2003 ).

Experimental

Crystal data

C₂₁H₃₀N₂O₅
M_r = 390.47
Triclinic, $[P \overline 1]$
a = 9.4140 (17) Å
b = 10.7606 (19) Å
c = 10.7874 (19) Å
α = 103.000 (4)°
β = 97.413 (4)°
γ = 97.736 (4)°
V = 1040.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.983, T_max = 0.987
8475 measured reflections
4252 independent reflections
2225 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.175
S = 1.00
4252 reflections
288 parameters
45 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5O⋯N4	0.87 (3)	1.87 (3)	2.714 (4)	163 (3)
N4—H4N⋯O2	0.86 (4)	2.23 (4)	2.971 (4)	144 (4)
N1—H1N⋯O4ⁱ	0.93 (3)	2.32 (3)	3.113 (3)	143
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054498/si2321sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054498/si2321Isup2.hkl

checkCIF report

Comment top

Established that β-cycloketoles and their nitrogenous derivatives possess a wide spectrum of biological activity (Krivenko et al. 2003). The reactions of β-cycloketoles with ethilendiamine possibly leading to valuable compounds of practical use remain unexplored. Reaction β-cycloketoles with ethilendiamine has not been studied. Several reaction paths may be expected: one or two reactive centers of the substrate and reagent may be involved. Enamines or the products of heterocyclization or spirocyclization may be produced.

In the title compound, C₂₁H₃₀N₂O₅ (I), the cyclohexane ring adopts a chair conformation. The structure of (I) is reported here (Fig. 1). The crystal structure involves N—H···O intermolecular and O—H···N and N—H···O intramolecular hydrogen bonds. (Table 1 and Fig. 2).

The cyclohexane ring has a chair conformation. The phenyl ring is in a pseudo-equatorial position. Torsion angle between the ethoxycarbonyl group and the phenyl substituent is C14—C7—C8—C20 is 55.4 (3) ° and C11—C6—C7—C14 is -53.4 (3) °, which indicates the pseudo-axial location of hydrogen atoms at C6 C7 and C8.

THe imidazolidine ring has a envelope conformation. The fragment of a ring N1—C2—C3—N4 is almost planar - torsion angle is -6.9 (3) °.

The molecules (I) are diastereomers and possess three asymmetric centers at th C6, C7, C8 and C9 carbon atoms. The crystal of (I) is racemate and consists of enantiomeric pairs with the relative configuration of the centers of rac-6S*,7R*, 8R*, 9S*.The two [(C7(R),C8(R)] of four stereogenic centres of (I) are of the same chirality.

Related literature top

For general background to the biological activity of β-cycloketoles and their nitrogenous derivatives, see: Krivenko et al. (2003).

Experimental top

(rac)-diethyl-4-hydroxy-4-methyl-6-oxo-2-phenyl-1,3-dicarboxylate (20 mmol), ethilendiamine (20 mmol) were dissolved in 20 ml e thanol. The mixture was stirred at 345–350 K within 10 h. After cooling to a room temperature obtained white crystals. The crystals were filtered and washed with ethanol and have been then dissolved in ethanol (50 ml) and recrystallized to yield colourless block-shaped crystals of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. The hydrogen-bonded (dashed lines) packing in the title compound. H atoms not involved in hydrogen bonding have been omitted for clarity.

rac-Diethyl 9-hydroxy-9-methyl-7-phenyl-1,4-diazaspiro[4.5]decane-6,8-dicarboxylate top

Crystal data top

C₂₁H₃₀N₂O₅	Z = 2
M_r = 390.47	F(000) = 420
Triclinic, P1	D_x = 1.246 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4140 (17) Å	Cell parameters from 1499 reflections
b = 10.7606 (19) Å	θ = 2.4–26.3°
c = 10.7874 (19) Å	µ = 0.09 mm⁻¹
α = 103.000 (4)°	T = 296 K
β = 97.413 (4)°	Prism, colorless
γ = 97.736 (4)°	0.20 × 0.20 × 0.15 mm
V = 1040.6 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	4252 independent reflections
Radiation source: fine-focus sealed tube	2225 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ϕ and ω scans	θ_max = 26.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.983, T_max = 0.987	k = −13→12
8475 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.068	Hydrogen site location: difference Fourier map
wR(F²) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.070P)²] where P = (F_o² + 2F_c²)/3
4252 reflections	(Δ/σ)_max = 0.001
288 parameters	Δρ_max = 0.30 e Å⁻³
45 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₁H₃₀N₂O₅	γ = 97.736 (4)°
M_r = 390.47	V = 1040.6 (3) Å³
Triclinic, P1	Z = 2
a = 9.4140 (17) Å	Mo Kα radiation
b = 10.7606 (19) Å	µ = 0.09 mm⁻¹
c = 10.7874 (19) Å	T = 296 K
α = 103.000 (4)°	0.20 × 0.20 × 0.15 mm
β = 97.413 (4)°

Data collection top

Bruker APEXII CCD diffractometer	4252 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2225 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.987	R_int = 0.065
8475 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	45 restraints
wR(F²) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.30 e Å⁻³
4252 reflections	Δρ_min = −0.25 e Å⁻³
288 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.3602 (2)	0.2303 (2)	0.8120 (2)	0.0732 (7)
O2	0.36432 (19)	0.2704 (2)	0.61942 (18)	0.0567 (6)
O3	0.91777 (17)	0.3860 (2)	0.62626 (17)	0.0562 (6)
O4	1.06405 (19)	0.4465 (3)	0.8161 (2)	0.0732 (7)
O5	0.7805 (2)	0.6254 (2)	0.68461 (18)	0.0491 (5)
H5O	0.688 (3)	0.594 (3)	0.660 (3)	0.058 (9)*
N1	0.3905 (2)	0.5684 (3)	0.8533 (2)	0.0424 (6)
H1N	0.315 (3)	0.499 (3)	0.833 (3)	0.050 (8)*
C2	0.3457 (3)	0.6699 (3)	0.7935 (3)	0.0564 (8)
H2A	0.3883	0.7548	0.8481	0.068*
H2B	0.2407	0.6629	0.7811	0.068*
C3	0.3994 (3)	0.6504 (3)	0.6627 (3)	0.0560 (8)
H3A	0.3178	0.6241	0.5923	0.067*
H3B	0.4564	0.7299	0.6558	0.067*
N4	0.4897 (2)	0.5477 (3)	0.6591 (2)	0.0429 (6)
H4N	0.441 (3)	0.474 (3)	0.615 (3)	0.066 (11)*
C5	0.5167 (2)	0.5335 (3)	0.7942 (2)	0.0364 (7)
C6	0.5414 (2)	0.3967 (3)	0.8005 (2)	0.0355 (6)
H6A	0.5591	0.3945	0.8915	0.043*
C7	0.6766 (2)	0.3630 (2)	0.7404 (2)	0.0342 (6)
H7A	0.6592	0.3675	0.6501	0.041*
C8	0.8119 (2)	0.4630 (3)	0.8092 (2)	0.0376 (6)
H8A	0.8285	0.4572	0.8991	0.045*
C9	0.7911 (2)	0.6047 (3)	0.8112 (2)	0.0411 (7)
C10	0.6525 (2)	0.6281 (3)	0.8664 (2)	0.0406 (7)
H10A	0.6666	0.6229	0.9556	0.049*
H10B	0.6369	0.7152	0.8654	0.049*
C11	0.4127 (2)	0.2941 (3)	0.7330 (3)	0.0412 (7)
C12	0.256 (2)	0.1166 (13)	0.7402 (10)	0.112 (8)	0.46 (3)
H12A	0.3007	0.0637	0.6758	0.134*	0.46 (3)
H12B	0.1726	0.1422	0.6967	0.134*	0.46 (3)
C13	0.210 (3)	0.0405 (15)	0.8359 (14)	0.132 (8)	0.46 (3)
H13A	0.2952	0.0263	0.8869	0.198*	0.46 (3)
H13B	0.1529	−0.0413	0.7897	0.198*	0.46 (3)
H13C	0.1541	0.0886	0.8912	0.198*	0.46 (3)
C12'	0.2401 (8)	0.1223 (6)	0.7744 (17)	0.094 (4)	0.54 (3)
H12C	0.2007	0.1075	0.6837	0.112*	0.54 (3)
H12D	0.1634	0.1405	0.8243	0.112*	0.54 (3)
C13'	0.299 (2)	0.0036 (7)	0.800 (2)	0.135 (7)	0.54 (3)
H13D	0.3728	−0.0150	0.7481	0.203*	0.54 (3)
H13E	0.2214	−0.0692	0.7781	0.203*	0.54 (3)
H13F	0.3400	0.0202	0.8894	0.203*	0.54 (3)
C14	0.6973 (2)	0.2259 (3)	0.7422 (2)	0.0410 (7)
C15	0.6688 (3)	0.1281 (3)	0.6296 (3)	0.0551 (8)
H15A	0.6359	0.1469	0.5519	0.066*
C16	0.6883 (4)	0.0033 (3)	0.6304 (4)	0.0686 (10)
H16A	0.6686	−0.0605	0.5534	0.082*
C17	0.7361 (4)	−0.0276 (4)	0.7424 (4)	0.0756 (11)
H17A	0.7496	−0.1116	0.7422	0.091*
C18	0.7639 (4)	0.0667 (4)	0.8552 (4)	0.0831 (12)
H18A	0.7956	0.0461	0.9322	0.100*
C19	0.7453 (3)	0.1934 (3)	0.8562 (3)	0.0623 (9)
H19A	0.7651	0.2565	0.9337	0.075*
C20	0.9451 (3)	0.4310 (3)	0.7527 (3)	0.0441 (7)
C21	1.0367 (3)	0.3475 (3)	0.5612 (3)	0.0775 (11)
H21A	1.1162	0.3383	0.6235	0.093*
H21B	1.0721	0.4128	0.5184	0.093*
C22	0.9815 (4)	0.2206 (4)	0.4639 (4)	0.1019 (15)
H22A	1.0557	0.1982	0.4138	0.153*
H22B	0.8969	0.2282	0.4079	0.153*
H22C	0.9568	0.1544	0.5078	0.153*
C23	0.9203 (3)	0.7006 (3)	0.8929 (3)	0.0595 (9)
H23A	0.8995	0.7868	0.9026	0.089*
H23B	1.0042	0.6927	0.8515	0.089*
H23C	0.9391	0.6829	0.9762	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0710 (13)	0.0810 (19)	0.0586 (13)	−0.0124 (13)	0.0097 (11)	0.0138 (13)
O2	0.0493 (11)	0.0633 (15)	0.0474 (12)	0.0136 (10)	−0.0061 (9)	−0.0016 (10)
O3	0.0418 (10)	0.0800 (16)	0.0534 (12)	0.0329 (10)	0.0173 (9)	0.0114 (11)
O4	0.0328 (10)	0.102 (2)	0.0834 (15)	0.0261 (11)	−0.0001 (10)	0.0167 (14)
O5	0.0466 (11)	0.0612 (15)	0.0510 (11)	0.0233 (10)	0.0172 (9)	0.0243 (10)
N1	0.0373 (12)	0.0513 (16)	0.0436 (12)	0.0239 (11)	0.0130 (10)	0.0089 (12)
C2	0.0543 (16)	0.057 (2)	0.0702 (19)	0.0360 (15)	0.0194 (14)	0.0199 (16)
C3	0.0556 (16)	0.065 (2)	0.0602 (18)	0.0365 (16)	0.0065 (14)	0.0272 (17)
N4	0.0445 (12)	0.0558 (18)	0.0309 (11)	0.0248 (12)	0.0012 (10)	0.0092 (12)
C5	0.0333 (12)	0.0494 (18)	0.0289 (12)	0.0223 (12)	0.0066 (10)	0.0048 (12)
C6	0.0328 (12)	0.0468 (17)	0.0287 (12)	0.0189 (11)	0.0048 (10)	0.0060 (12)
C7	0.0347 (12)	0.0427 (17)	0.0283 (12)	0.0194 (11)	0.0038 (10)	0.0080 (11)
C8	0.0344 (12)	0.0480 (18)	0.0330 (13)	0.0178 (12)	0.0033 (10)	0.0104 (12)
C9	0.0373 (13)	0.0495 (18)	0.0394 (14)	0.0176 (12)	0.0062 (11)	0.0109 (13)
C10	0.0411 (13)	0.0472 (18)	0.0348 (13)	0.0206 (12)	0.0053 (11)	0.0057 (12)
C11	0.0345 (12)	0.0481 (19)	0.0409 (15)	0.0189 (12)	0.0089 (12)	0.0020 (14)
C12	0.108 (9)	0.134 (15)	0.063 (8)	−0.066 (9)	0.013 (6)	0.011 (7)
C13	0.190 (18)	0.095 (11)	0.097 (8)	−0.027 (11)	0.049 (9)	0.012 (8)
C12'	0.117 (8)	0.091 (9)	0.059 (6)	−0.032 (7)	0.021 (6)	0.018 (5)
C13'	0.158 (12)	0.082 (8)	0.148 (13)	−0.023 (7)	−0.012 (9)	0.036 (9)
C14	0.0328 (12)	0.0499 (18)	0.0425 (14)	0.0192 (12)	0.0078 (11)	0.0080 (13)
C15	0.0654 (18)	0.055 (2)	0.0471 (16)	0.0271 (15)	0.0097 (14)	0.0066 (15)
C16	0.082 (2)	0.052 (2)	0.072 (2)	0.0242 (18)	0.0210 (18)	0.0047 (19)
C17	0.087 (2)	0.049 (2)	0.103 (3)	0.0321 (19)	0.022 (2)	0.027 (2)
C18	0.107 (3)	0.078 (3)	0.077 (3)	0.040 (2)	0.003 (2)	0.039 (2)
C19	0.084 (2)	0.058 (2)	0.0484 (17)	0.0287 (18)	−0.0020 (15)	0.0175 (16)
C20	0.0327 (13)	0.0464 (18)	0.0576 (17)	0.0181 (12)	0.0078 (12)	0.0150 (14)
C21	0.0517 (17)	0.095 (3)	0.096 (3)	0.0381 (18)	0.0391 (17)	0.012 (2)
C22	0.078 (2)	0.111 (4)	0.109 (3)	0.032 (2)	0.045 (2)	−0.014 (3)
C23	0.0449 (15)	0.057 (2)	0.073 (2)	0.0142 (14)	0.0044 (14)	0.0068 (17)

Geometric parameters (Å, º) top

O1—C11	1.312 (4)	C10—H10B	0.9700
O1—C12	1.452 (3)	C12—C13	1.524 (3)
O1—C12'	1.452 (3)	C12—H12A	0.9700
O2—C11	1.207 (3)	C12—H12B	0.9700
O3—C20	1.319 (3)	C13—H13A	0.9600
O3—C21	1.454 (2)	C13—H13B	0.9600
O4—C20	1.204 (3)	C13—H13C	0.9600
O5—C9	1.426 (3)	C12'—C13'	1.525 (3)
O5—H5O	0.87 (3)	C12'—H12C	0.9700
N1—C2	1.469 (4)	C12'—H12D	0.9700
N1—C5	1.472 (3)	C13'—H13D	0.9600
N1—H1N	0.93 (3)	C13'—H13E	0.9600
C2—C3	1.539 (4)	C13'—H13F	0.9600
C2—H2A	0.9700	C14—C15	1.385 (4)
C2—H2B	0.9700	C14—C19	1.390 (4)
C3—N4	1.479 (3)	C15—C16	1.382 (5)
C3—H3A	0.9700	C15—H15A	0.9300
C3—H3B	0.9700	C16—C17	1.361 (5)
N4—C5	1.491 (3)	C16—H16A	0.9300
N4—H4N	0.86 (3)	C17—C18	1.367 (5)
C5—C10	1.521 (4)	C17—H17A	0.9300
C5—C6	1.536 (4)	C18—C19	1.395 (5)
C6—C11	1.507 (4)	C18—H18A	0.9300
C6—C7	1.550 (3)	C19—H19A	0.9300
C6—H6A	0.9800	C21—C22	1.503 (3)
C7—C14	1.518 (4)	C21—H21A	0.9700
C7—C8	1.536 (3)	C21—H21B	0.9700
C7—H7A	0.9800	C22—H22A	0.9600
C8—C20	1.511 (3)	C22—H22B	0.9600
C8—C9	1.558 (4)	C22—H22C	0.9600
C8—H8A	0.9800	C23—H23A	0.9600
C9—C23	1.515 (4)	C23—H23B	0.9600
C9—C10	1.531 (3)	C23—H23C	0.9600
C10—H10A	0.9700

C11—O1—C12	110.4 (5)	O2—C11—C6	124.7 (3)
C11—O1—C12'	124.8 (8)	O1—C11—C6	111.8 (2)
C12—O1—C12'	16.3 (9)	O1—C12—C13	107.8 (3)
C20—O3—C21	117.9 (2)	O1—C12—H12A	110.2
C9—O5—H5O	97 (2)	C13—C12—H12A	110.2
C2—N1—C5	104.2 (2)	O1—C12—H12B	110.2
C2—N1—H1N	108.9 (19)	C13—C12—H12B	110.2
C5—N1—H1N	111.4 (16)	H12A—C12—H12B	108.5
N1—C2—C3	107.0 (2)	O1—C12'—C13'	107.4 (3)
N1—C2—H2A	110.3	O1—C12'—H12C	110.2
C3—C2—H2A	110.3	C13'—C12'—H12C	110.2
N1—C2—H2B	110.3	O1—C12'—H12D	110.2
C3—C2—H2B	110.3	C13'—C12'—H12D	110.2
H2A—C2—H2B	108.6	H12C—C12'—H12D	108.5
N4—C3—C2	105.8 (2)	C12'—C13'—H13D	109.5
N4—C3—H3A	110.6	C12'—C13'—H13E	109.5
C2—C3—H3A	110.6	H13D—C13'—H13E	109.5
N4—C3—H3B	110.6	C12'—C13'—H13F	109.5
C2—C3—H3B	110.6	H13D—C13'—H13F	109.5
H3A—C3—H3B	108.7	H13E—C13'—H13F	109.5
C3—N4—C5	105.42 (19)	C15—C14—C19	117.4 (3)
C3—N4—H4N	111 (2)	C15—C14—C7	121.0 (2)
C5—N4—H4N	105 (2)	C19—C14—C7	121.6 (2)
N1—C5—N4	106.77 (18)	C16—C15—C14	121.3 (3)
N1—C5—C10	109.25 (19)	C16—C15—H15A	119.3
N4—C5—C10	108.6 (2)	C14—C15—H15A	119.3
N1—C5—C6	111.7 (2)	C17—C16—C15	120.9 (3)
N4—C5—C6	112.5 (2)	C17—C16—H16A	119.6
C10—C5—C6	107.91 (19)	C15—C16—H16A	119.6
C11—C6—C5	112.78 (19)	C16—C17—C18	119.1 (3)
C11—C6—C7	108.50 (18)	C16—C17—H17A	120.4
C5—C6—C7	110.9 (2)	C18—C17—H17A	120.4
C11—C6—H6A	108.2	C17—C18—C19	120.9 (4)
C5—C6—H6A	108.2	C17—C18—H18A	119.6
C7—C6—H6A	108.2	C19—C18—H18A	119.6
C14—C7—C8	112.20 (19)	C14—C19—C18	120.4 (3)
C14—C7—C6	110.7 (2)	C14—C19—H19A	119.8
C8—C7—C6	110.38 (18)	C18—C19—H19A	119.8
C14—C7—H7A	107.8	O4—C20—O3	123.6 (2)
C8—C7—H7A	107.8	O4—C20—C8	123.6 (3)
C6—C7—H7A	107.8	O3—C20—C8	112.8 (2)
C20—C8—C7	111.2 (2)	O3—C21—C22	108.4 (2)
C20—C8—C9	111.4 (2)	O3—C21—H21A	110.0
C7—C8—C9	112.87 (18)	C22—C21—H21A	110.0
C20—C8—H8A	107.0	O3—C21—H21B	110.0
C7—C8—H8A	107.0	C22—C21—H21B	110.0
C9—C8—H8A	107.0	H21A—C21—H21B	108.4
O5—C9—C23	106.6 (2)	C21—C22—H22A	109.5
O5—C9—C10	110.33 (19)	C21—C22—H22B	109.5
C23—C9—C10	110.1 (2)	H22A—C22—H22B	109.5
O5—C9—C8	110.8 (2)	C21—C22—H22C	109.5
C23—C9—C8	110.9 (2)	H22A—C22—H22C	109.5
C10—C9—C8	108.1 (2)	H22B—C22—H22C	109.5
C5—C10—C9	114.35 (19)	C9—C23—H23A	109.5
C5—C10—H10A	108.7	C9—C23—H23B	109.5
C9—C10—H10A	108.7	H23A—C23—H23B	109.5
C5—C10—H10B	108.7	C9—C23—H23C	109.5
C9—C10—H10B	108.7	H23A—C23—H23C	109.5
H10A—C10—H10B	107.6	H23B—C23—H23C	109.5
O2—C11—O1	123.4 (3)

C5—N1—C2—C3	24.6 (3)	C23—C9—C10—C5	−177.9 (2)
N1—C2—C3—N4	−6.9 (3)	C8—C9—C10—C5	−56.6 (3)
C2—C3—N4—C5	−13.4 (3)	C12—O1—C11—O2	9.9 (12)
C2—N1—C5—N4	−33.6 (3)	C12'—O1—C11—O2	1.2 (6)
C2—N1—C5—C10	83.7 (3)	C12—O1—C11—C6	−168.6 (11)
C2—N1—C5—C6	−157.0 (2)	C12'—O1—C11—C6	−177.4 (5)
C3—N4—C5—N1	29.4 (3)	C5—C6—C11—O2	61.6 (3)
C3—N4—C5—C10	−88.3 (2)	C7—C6—C11—O2	−61.6 (3)
C3—N4—C5—C6	152.3 (2)	C5—C6—C11—O1	−119.8 (2)
N1—C5—C6—C11	59.3 (3)	C7—C6—C11—O1	116.9 (2)
N4—C5—C6—C11	−60.8 (3)	C11—O1—C12—C13	175 (2)
C10—C5—C6—C11	179.39 (18)	C12'—O1—C12—C13	−32 (3)
N1—C5—C6—C7	−178.81 (18)	C11—O1—C12'—C13'	116.7 (18)
N4—C5—C6—C7	61.1 (2)	C12—O1—C12'—C13'	86 (4)
C10—C5—C6—C7	−58.7 (2)	C8—C7—C14—C15	−128.3 (2)
C11—C6—C7—C14	−53.4 (3)	C6—C7—C14—C15	107.9 (3)
C5—C6—C7—C14	−177.81 (19)	C8—C7—C14—C19	51.7 (3)
C11—C6—C7—C8	−178.3 (2)	C6—C7—C14—C19	−72.1 (3)
C5—C6—C7—C8	57.3 (3)	C19—C14—C15—C16	−0.5 (4)
C14—C7—C8—C20	55.4 (3)	C7—C14—C15—C16	179.6 (3)
C6—C7—C8—C20	179.4 (2)	C14—C15—C16—C17	0.1 (5)
C14—C7—C8—C9	−178.55 (19)	C15—C16—C17—C18	0.4 (5)
C6—C7—C8—C9	−54.5 (3)	C16—C17—C18—C19	−0.6 (6)
C20—C8—C9—O5	57.6 (3)	C15—C14—C19—C18	0.2 (5)
C7—C8—C9—O5	−68.3 (2)	C7—C14—C19—C18	−179.8 (3)
C20—C8—C9—C23	−60.6 (3)	C17—C18—C19—C14	0.3 (6)
C7—C8—C9—C23	173.5 (2)	C21—O3—C20—O4	3.1 (4)
C20—C8—C9—C10	178.6 (2)	C21—O3—C20—C8	−177.9 (2)
C7—C8—C9—C10	52.7 (3)	C7—C8—C20—O4	−142.5 (3)
N1—C5—C10—C9	−178.1 (2)	C9—C8—C20—O4	90.6 (3)
N4—C5—C10—C9	−62.0 (3)	C7—C8—C20—O3	38.5 (3)
C6—C5—C10—C9	60.2 (3)	C9—C8—C20—O3	−88.4 (3)
O5—C9—C10—C5	64.7 (3)	C20—O3—C21—C22	135.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···N4	0.87 (3)	1.87 (3)	2.714 (4)	163 (3)
N4—H4N···O2	0.86 (4)	2.23 (4)	2.971 (4)	144 (4)
N1—H1N···O4ⁱ	0.93 (3)	2.32 (3)	3.113 (3)	143

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₃₀N₂O₅
M_r	390.47
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.4140 (17), 10.7606 (19), 10.7874 (19)
α, β, γ (°)	103.000 (4), 97.413 (4), 97.736 (4)
V (Å³)	1040.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.983, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	8475, 4252, 2225
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.175, 1.00
No. of reflections	4252
No. of parameters	288
No. of restraints	45
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.25

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXL97 (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5O···N4	0.87 (3)	1.87 (3)	2.714 (4)	163 (3)
N4—H4N···O2	0.86 (4)	2.23 (4)	2.971 (4)	144 (4)
N1—H1N···O4ⁱ	0.93 (3)	2.32 (3)	3.113 (3)	143

Symmetry code: (i) x−1, y, z.

Acknowledgements

We thank Professor Victor N. Khrustalev for fruitful discussions and help with this work.

References

Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Krivenko, A. P., Kozlova, E. A., Grigorev, A. V. & Sorokin, V. V. (2003). Molecules, 8, 251-255. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Page o291

doi:10.1107/S1600536810054498

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

rac-Di­ethyl 9-hy­dr­oxy-9-methyl-7-phenyl-1,4-di­aza­spiro­[4.5]decane-6,8-di­carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-Diethyl 9-hydroxy-9-methyl-7-phenyl-1,4-diazaspiro[4.5]decane-6,8-dicarboxylate