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

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ISSN: 2056-9890

cis-3-(tert-But­oxy­carbonyl­amino)cyclo­hexa­ne­carboxylic acid

aExperimental Chemistry Center, Nanchang University, Nanchang 330031, People's Republic of China, and bJiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, People's Republic of China
*Correspondence e-mail: huyu@ncu.edu.cn

(Received 21 August 2008; accepted 22 August 2008; online 30 August 2008)

The title compound, C12H21NO4, a γ-aminobutyric acid derivative, crystallizes with two mol­ecules in the asymmetric unit. The crystal structure is stabilized by inter­molecular N—H⋯O and O—H⋯O hydrogen bonds, forming a strand. An intramolecular N—H⋯O hydrogen bond is also observed.

Related literature

For related literature, see: Allan et al. (1981[Allan, R. D., Johnston, G. A. R. & Twitchin, B. (1981). Aust. J. Chem. 34, 2231-2236.]); Amorin et al. (2003[Amorin, M., Castedo, L. & Granja, J. R. (2003). J. Am. Chem. Soc. 125, 2844-2845.]); Hu et al. (2006[Hu, Y., Yu, S. L., Yang, Y. J., Zhu, J. & Deng, J. G. (2006). Chin. J. Chem. 24, 795-799.]); Roberts et al. (1976[Roberts, E., Chase, T. N. & Towes, D. B. (1976). GABA in Nervous System Function. New York: Raven Press.]); Schousboe (2000[Schousboe, A. (2000). Neurochem. Res. 25, 1241-1244.]).

[Scheme 1]

Experimental

Crystal data
  • C12H21NO4

  • Mr = 243.30

  • Triclinic, [P \overline 1]

  • a = 5.854 (1) Å

  • b = 10.000 (2) Å

  • c = 23.014 (5) Å

  • α = 85.64 (2)°

  • β = 88.68 (2)°

  • γ = 88.51 (2)°

  • V = 1342.6 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 (2) K

  • 0.56 × 0.46 × 0.20 mm

Data collection
  • Bruker SMART 1K area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.767, Tmax = 0.921 (expected range = 0.818–0.982)

  • 5514 measured reflections

  • 4822 independent reflections

  • 2483 reflections with I > 2σ(I)

  • Rint = 0.017

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.109

  • S = 0.81

  • 4822 reflections

  • 324 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O6 0.856 (9) 2.163 (10) 3.009 (2) 169 (2)
N2—H2A⋯O2i 0.854 (9) 2.180 (11) 3.013 (2) 164.9 (19)
O3—H3⋯O4ii 0.82 1.86 2.672 (2) 172
O7—H7⋯O8iii 0.82 1.84 2.656 (2) 171
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT-Plus. Bruker AXS Inc, Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999[Bruker (1999). SMART and SAINT-Plus. Bruker AXS Inc, Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

γ aminobutyric acid (GABA) and its derivatives have an extensive appliction in medicine. For instance, GABA is an important inhibitory neurotransmitter in certain neurological and psychiatric disorders (Schousboe, 2000; Roberts et al., 1976). As the analogue of GABA, cis-3-aminocyclohexanecarboxylic acid is an inhibitor of GABA uptake (Allan et al., 1981). cis-3-aminocyclohexanecarboxylic acid is incorporated in cyclic peptides and organic nanotubes (Amorin et al., 2003). The title compound is a key intermediate for the synthesis of cis-3- aminocyclohexanecarboxylic acid (Hu et al., 2006). The synthesis and crystal structure of the title compound are described in this paper.

Interolecular O-H···O hydrogen bonds result in eight-membered rings that can be described in terms of graph-set notation as R22(8) (Figure 2).

One-dimensional strands are formed along the crystallographic b axis by N-H···O hydrogen bonds (Figure 2 and Table 2).

Related literature top

For related literature, see: Allan et al. (1981); Amorin et al. (2003); Hu et al. (2006); Roberts et al. (1976); Schousboe (2000).

Experimental top

cis-3-tert-butoxycarbonylamino-cyclohexanecarboxylic acid was synthesized from 3-aminobenzoic acid (Amorin et al., 2003). The compound identity was conformed by the NMR spectra and IR. Crystal were obtained from ethyl acetate by solvent evaporation. 1H NMR in CDCl3 (300 MHz): 9.20–10.4 (br, 1H,), 5.72 (s, 1H), 4.82 (s, H), 3.67–3.74 (m, 1H), 1.43 (s, 9H), 1.05–2.40 (m, 8H).

Refinement top

H atoms bonded to C and O were geometrically positioned and treated as riding on their parent C atoms, with C—H distances in the range of 0.82–0.98 Å, with Uiso (H) = 1.2–1.5 times Ueq of the parent atom. H atoms attached to N1 and N2 were located in difference Fourier maps and refined initially with the N-H distance restrained to 0.86 Å.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the two molecules in the asymmetric unit of the title compound, with anisotropic displacement parameters drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the hydrogen-bonded strands (Dashed lines). The strands are aligned parallel to the crystallographic b axis. H atoms not involved in H-bonding have been omitted for clarity. Symmetry codes: (*) x,y+1,z; (**) x,y-1,z; (#) 1 - x,1 - y,-z; (##) 1 - x,2 - y,-z.
cis-3-(tert-Butoxycarbonylamino)cyclohexanecarboxylic acid top
Crystal data top
C12H21NO4Z = 4
Mr = 243.30F(000) = 528
Triclinic, P1Dx = 1.204 Mg m3
Hall symbol: -P 1Melting point: 409 K
a = 5.854 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.000 (2) ÅCell parameters from 29 reflections
c = 23.014 (5) Åθ = 4.1–13.9°
α = 85.64 (2)°µ = 0.09 mm1
β = 88.68 (2)°T = 296 K
γ = 88.51 (2)°Block, colorless
V = 1342.6 (4) Å30.56 × 0.46 × 0.20 mm
Data collection top
Bruker SMART 1K area-detector
diffractometer
4822 independent reflections
Radiation source: fine-focus sealed tube2483 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
phi and ω scansθmax = 25.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 07
Tmin = 0.767, Tmax = 0.921k = 1111
5514 measured reflectionsl = 2727
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)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0564P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.81(Δ/σ)max < 0.001
4822 reflectionsΔρmax = 0.22 e Å3
324 parametersΔρmin = 0.17 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0098 (13)
Crystal data top
C12H21NO4γ = 88.51 (2)°
Mr = 243.30V = 1342.6 (4) Å3
Triclinic, P1Z = 4
a = 5.854 (1) ÅMo Kα radiation
b = 10.000 (2) ŵ = 0.09 mm1
c = 23.014 (5) ÅT = 296 K
α = 85.64 (2)°0.56 × 0.46 × 0.20 mm
β = 88.68 (2)°
Data collection top
Bruker SMART 1K area-detector
diffractometer
4822 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2483 reflections with I > 2σ(I)
Tmin = 0.767, Tmax = 0.921Rint = 0.017
5514 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0442 restraints
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 0.81Δρmax = 0.22 e Å3
4822 reflectionsΔρmin = 0.17 e Å3
324 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
xyzUiso*/Ueq
O10.6276 (3)0.87356 (14)0.15126 (6)0.0548 (5)
O20.5946 (3)1.03347 (15)0.21599 (7)0.0620 (5)
O30.6134 (3)0.64184 (19)0.45997 (9)0.0823 (6)
H30.63550.57780.48380.099*
O40.2737 (3)0.55582 (18)0.46040 (8)0.0797 (6)
N10.4694 (4)0.82327 (18)0.23756 (7)0.0481 (5)
C10.4318 (4)0.7291 (2)0.33857 (8)0.0408 (5)
H1C0.59600.71360.33920.049*
H1B0.36230.64900.32650.049*
C20.3427 (4)0.7572 (2)0.39994 (8)0.0384 (5)
H20.41830.83720.41130.046*
C30.0867 (4)0.7873 (2)0.39991 (9)0.0467 (6)
H3A0.00690.70800.39060.056*
H3B0.03580.80990.43840.056*
C40.0288 (4)0.9027 (2)0.35566 (10)0.0525 (6)
H4A0.09380.98430.36770.063*
H4B0.13580.91600.35460.063*
C50.1199 (4)0.8768 (2)0.29489 (9)0.0536 (6)
H5A0.04240.80110.28100.064*
H5B0.08800.95470.26840.064*
C60.3752 (4)0.8474 (2)0.29527 (8)0.0403 (5)
H60.44930.92630.30830.048*
C70.5654 (4)0.9200 (2)0.20301 (9)0.0437 (6)
C80.7620 (4)0.9548 (2)0.10769 (9)0.0483 (6)
C90.6330 (5)1.0795 (3)0.08659 (11)0.0732 (8)
H9A0.48241.05670.07560.088*
H9B0.71201.12210.05350.088*
H9C0.62161.13970.11710.088*
C100.7906 (6)0.8626 (3)0.05895 (11)0.0877 (10)
H10A0.87050.78190.07290.105*
H10B0.87660.90660.02730.105*
H10C0.64300.84080.04560.105*
C110.9874 (5)0.9845 (3)0.13189 (13)0.0946 (11)
H11A0.96631.04920.16040.114*
H11B1.08661.02000.10100.114*
H11C1.05460.90360.14990.114*
C120.4076 (4)0.6421 (2)0.44293 (9)0.0414 (5)
O50.3565 (3)0.37430 (14)0.15151 (6)0.0550 (5)
O60.3842 (3)0.53682 (15)0.21453 (6)0.0597 (5)
O70.3647 (3)0.1116 (2)0.44631 (8)0.0765 (6)
H70.34450.05710.47430.092*
O80.7245 (3)0.08103 (17)0.47100 (7)0.0692 (5)
N20.5105 (3)0.32454 (17)0.23698 (7)0.0458 (5)
C130.5512 (4)0.2287 (2)0.33700 (8)0.0401 (5)
H13A0.63270.15040.32400.048*
H13B0.38920.21020.33850.048*
C140.6306 (4)0.2564 (2)0.39808 (8)0.0382 (5)
H140.54240.33470.41000.046*
C150.8821 (4)0.2927 (2)0.39721 (9)0.0477 (6)
H15A0.97570.21590.38730.057*
H15B0.92430.31590.43560.057*
C160.9262 (4)0.4108 (2)0.35278 (10)0.0543 (6)
H16A0.84740.49020.36560.065*
H16B1.08860.42800.35070.065*
C170.8453 (4)0.3842 (2)0.29241 (9)0.0536 (6)
H17A0.86780.46340.26600.064*
H17B0.93580.31100.27770.064*
C180.5954 (4)0.3489 (2)0.29415 (8)0.0395 (5)
H180.50810.42560.30800.047*
C190.4147 (4)0.4221 (2)0.20222 (9)0.0426 (6)
C200.2250 (4)0.4572 (2)0.10807 (9)0.0482 (6)
C210.3591 (5)0.5763 (3)0.08456 (11)0.0705 (8)
H21A0.37710.63590.11480.085*
H21B0.27910.62250.05280.085*
H21C0.50690.54650.07100.085*
C220.1969 (6)0.3620 (3)0.06073 (11)0.0893 (10)
H22A0.34470.33470.04630.107*
H22B0.11170.40650.02940.107*
H22C0.11640.28450.07640.107*
C230.0011 (5)0.4961 (3)0.13346 (12)0.0863 (10)
H23A0.07160.41820.15220.104*
H23B0.09720.53460.10300.104*
H23C0.01980.56070.16160.104*
C240.5776 (4)0.1408 (2)0.44197 (9)0.0426 (6)
H1A0.452 (4)0.7445 (12)0.2264 (9)0.048 (7)*
H2A0.522 (3)0.2460 (12)0.2249 (8)0.039 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0864 (13)0.0413 (9)0.0361 (9)0.0087 (8)0.0145 (8)0.0006 (7)
O20.1046 (15)0.0365 (9)0.0447 (10)0.0099 (9)0.0104 (9)0.0030 (8)
O30.0604 (13)0.0895 (15)0.0894 (15)0.0081 (11)0.0195 (11)0.0498 (11)
O40.0745 (14)0.0736 (13)0.0854 (14)0.0219 (11)0.0229 (10)0.0437 (11)
N10.0844 (16)0.0307 (11)0.0288 (10)0.0057 (10)0.0068 (9)0.0015 (9)
C10.0493 (14)0.0388 (12)0.0334 (12)0.0036 (10)0.0013 (10)0.0006 (9)
C20.0499 (14)0.0344 (11)0.0305 (11)0.0003 (10)0.0030 (10)0.0003 (9)
C30.0507 (15)0.0479 (14)0.0408 (13)0.0026 (11)0.0020 (11)0.0007 (11)
C40.0536 (16)0.0525 (14)0.0504 (14)0.0098 (12)0.0034 (12)0.0003 (12)
C50.0667 (18)0.0530 (15)0.0399 (14)0.0098 (13)0.0113 (12)0.0041 (11)
C60.0584 (16)0.0356 (12)0.0266 (11)0.0001 (11)0.0007 (10)0.0006 (9)
C70.0648 (17)0.0345 (13)0.0313 (12)0.0029 (11)0.0034 (11)0.0006 (10)
C80.0589 (16)0.0491 (14)0.0350 (12)0.0040 (12)0.0051 (11)0.0082 (11)
C90.087 (2)0.0726 (18)0.0554 (16)0.0072 (16)0.0048 (15)0.0203 (14)
C100.139 (3)0.073 (2)0.0496 (17)0.0045 (19)0.0331 (17)0.0041 (15)
C110.066 (2)0.142 (3)0.071 (2)0.012 (2)0.0066 (16)0.028 (2)
C120.0492 (16)0.0454 (14)0.0294 (12)0.0024 (12)0.0003 (11)0.0003 (10)
O50.0900 (13)0.0407 (9)0.0344 (9)0.0082 (8)0.0216 (8)0.0015 (7)
O60.1010 (14)0.0325 (9)0.0460 (10)0.0044 (9)0.0174 (9)0.0025 (7)
O70.0646 (13)0.0912 (15)0.0673 (13)0.0167 (11)0.0103 (10)0.0429 (10)
O80.0616 (12)0.0802 (12)0.0598 (11)0.0021 (10)0.0067 (9)0.0342 (10)
N20.0777 (15)0.0305 (11)0.0291 (10)0.0044 (10)0.0097 (9)0.0011 (9)
C130.0491 (14)0.0377 (12)0.0334 (12)0.0032 (10)0.0063 (10)0.0011 (9)
C140.0526 (15)0.0335 (11)0.0281 (11)0.0002 (10)0.0027 (10)0.0006 (9)
C150.0576 (16)0.0470 (14)0.0385 (13)0.0052 (11)0.0095 (11)0.0003 (10)
C160.0569 (16)0.0544 (15)0.0516 (15)0.0155 (12)0.0063 (12)0.0035 (12)
C170.0651 (18)0.0549 (15)0.0389 (13)0.0094 (13)0.0045 (12)0.0093 (11)
C180.0570 (15)0.0332 (11)0.0281 (11)0.0003 (10)0.0029 (10)0.0002 (9)
C190.0587 (16)0.0353 (13)0.0333 (12)0.0016 (11)0.0043 (11)0.0008 (10)
C200.0588 (16)0.0518 (14)0.0322 (12)0.0036 (12)0.0077 (11)0.0098 (11)
C210.078 (2)0.0773 (19)0.0532 (16)0.0065 (16)0.0084 (14)0.0206 (14)
C220.138 (3)0.076 (2)0.0557 (18)0.0055 (19)0.0464 (18)0.0007 (15)
C230.063 (2)0.125 (3)0.0653 (19)0.0061 (18)0.0004 (15)0.0247 (18)
C240.0528 (16)0.0483 (14)0.0265 (11)0.0041 (12)0.0032 (11)0.0007 (10)
Geometric parameters (Å, º) top
O1—C71.350 (2)O5—C191.349 (2)
O1—C81.468 (2)O5—C201.468 (2)
O2—C71.212 (2)O6—C191.210 (2)
O3—C121.276 (3)O7—C241.288 (3)
O3—H30.8200O7—H70.8200
O4—C121.220 (2)O8—C241.217 (2)
N1—C71.332 (3)N2—C191.334 (3)
N1—C61.461 (3)N2—C181.457 (3)
N1—H1A0.856 (9)N2—H2A0.854 (9)
C1—C61.522 (3)C13—C181.519 (3)
C1—C21.538 (3)C13—C141.538 (3)
C1—H1C0.9700C13—H13A0.9700
C1—H1B0.9700C13—H13B0.9700
C2—C121.507 (3)C14—C241.510 (3)
C2—C31.521 (3)C14—C151.525 (3)
C2—H20.9800C14—H140.9800
C3—C41.517 (3)C15—C161.526 (3)
C3—H3A0.9700C15—H15A0.9700
C3—H3B0.9700C15—H15B0.9700
C4—C51.524 (3)C16—C171.522 (3)
C4—H4A0.9700C16—H16A0.9700
C4—H4B0.9700C16—H16B0.9700
C5—C61.515 (3)C17—C181.513 (3)
C5—H5A0.9700C17—H17A0.9700
C5—H5B0.9700C17—H17B0.9700
C6—H60.9800C18—H180.9800
C8—C111.490 (3)C20—C231.489 (3)
C8—C91.496 (3)C20—C211.503 (3)
C8—C101.509 (3)C20—C221.515 (3)
C9—H9A0.9600C21—H21A0.9600
C9—H9B0.9600C21—H21B0.9600
C9—H9C0.9600C21—H21C0.9600
C10—H10A0.9600C22—H22A0.9600
C10—H10B0.9600C22—H22B0.9600
C10—H10C0.9600C22—H22C0.9600
C11—H11A0.9600C23—H23A0.9600
C11—H11B0.9600C23—H23B0.9600
C11—H11C0.9600C23—H23C0.9600
C7—O1—C8121.42 (16)C19—O5—C20121.23 (16)
C12—O3—H3109.5C24—O7—H7109.5
C7—N1—C6122.03 (18)C19—N2—C18121.92 (17)
C7—N1—H1A122.0 (15)C19—N2—H2A118.2 (14)
C6—N1—H1A115.9 (15)C18—N2—H2A119.8 (14)
C6—C1—C2110.34 (16)C18—C13—C14110.31 (16)
C6—C1—H1C109.6C18—C13—H13A109.6
C2—C1—H1C109.6C14—C13—H13A109.6
C6—C1—H1B109.6C18—C13—H13B109.6
C2—C1—H1B109.6C14—C13—H13B109.6
H1C—C1—H1B108.1H13A—C13—H13B108.1
C12—C2—C3112.57 (18)C24—C14—C15112.45 (18)
C12—C2—C1109.99 (16)C24—C14—C13111.16 (16)
C3—C2—C1110.88 (17)C15—C14—C13111.45 (17)
C12—C2—H2107.7C24—C14—H14107.2
C3—C2—H2107.7C15—C14—H14107.2
C1—C2—H2107.7C13—C14—H14107.2
C4—C3—C2110.80 (18)C14—C15—C16110.42 (18)
C4—C3—H3A109.5C14—C15—H15A109.6
C2—C3—H3A109.5C16—C15—H15A109.6
C4—C3—H3B109.5C14—C15—H15B109.6
C2—C3—H3B109.5C16—C15—H15B109.6
H3A—C3—H3B108.1H15A—C15—H15B108.1
C3—C4—C5111.78 (18)C17—C16—C15111.92 (18)
C3—C4—H4A109.3C17—C16—H16A109.2
C5—C4—H4A109.3C15—C16—H16A109.2
C3—C4—H4B109.3C17—C16—H16B109.2
C5—C4—H4B109.3C15—C16—H16B109.2
H4A—C4—H4B107.9H16A—C16—H16B107.9
C6—C5—C4111.06 (18)C18—C17—C16111.07 (18)
C6—C5—H5A109.4C18—C17—H17A109.4
C4—C5—H5A109.4C16—C17—H17A109.4
C6—C5—H5B109.4C18—C17—H17B109.4
C4—C5—H5B109.4C16—C17—H17B109.4
H5A—C5—H5B108.0H17A—C17—H17B108.0
N1—C6—C5112.69 (18)N2—C18—C17112.74 (18)
N1—C6—C1110.26 (16)N2—C18—C13110.10 (16)
C5—C6—C1110.66 (18)C17—C18—C13111.08 (17)
N1—C6—H6107.7N2—C18—H18107.6
C5—C6—H6107.7C17—C18—H18107.6
C1—C6—H6107.7C13—C18—H18107.6
O2—C7—N1125.2 (2)O6—C19—N2124.8 (2)
O2—C7—O1124.5 (2)O6—C19—O5125.00 (19)
N1—C7—O1110.26 (18)N2—C19—O5110.16 (18)
O1—C8—C11109.95 (19)O5—C20—C23110.03 (18)
O1—C8—C9111.3 (2)O5—C20—C21110.79 (19)
C11—C8—C9112.2 (2)C23—C20—C21112.6 (2)
O1—C8—C10102.23 (18)O5—C20—C22102.20 (18)
C11—C8—C10111.0 (2)C23—C20—C22110.8 (2)
C9—C8—C10109.7 (2)C21—C20—C22109.9 (2)
C8—C9—H9A109.5C20—C21—H21A109.5
C8—C9—H9B109.5C20—C21—H21B109.5
H9A—C9—H9B109.5H21A—C21—H21B109.5
C8—C9—H9C109.5C20—C21—H21C109.5
H9A—C9—H9C109.5H21A—C21—H21C109.5
H9B—C9—H9C109.5H21B—C21—H21C109.5
C8—C10—H10A109.5C20—C22—H22A109.5
C8—C10—H10B109.5C20—C22—H22B109.5
H10A—C10—H10B109.5H22A—C22—H22B109.5
C8—C10—H10C109.5C20—C22—H22C109.5
H10A—C10—H10C109.5H22A—C22—H22C109.5
H10B—C10—H10C109.5H22B—C22—H22C109.5
C8—C11—H11A109.5C20—C23—H23A109.5
C8—C11—H11B109.5C20—C23—H23B109.5
H11A—C11—H11B109.5H23A—C23—H23B109.5
C8—C11—H11C109.5C20—C23—H23C109.5
H11A—C11—H11C109.5H23A—C23—H23C109.5
H11B—C11—H11C109.5H23B—C23—H23C109.5
O4—C12—O3122.4 (2)O8—C24—O7123.0 (2)
O4—C12—C2122.7 (2)O8—C24—C14122.6 (2)
O3—C12—C2114.9 (2)O7—C24—C14114.4 (2)
C6—C1—C2—C12177.75 (18)C18—C13—C14—C24177.21 (18)
C6—C1—C2—C357.1 (2)C18—C13—C14—C1556.5 (2)
C12—C2—C3—C4179.43 (18)C24—C14—C15—C16179.33 (18)
C1—C2—C3—C455.7 (2)C13—C14—C15—C1655.1 (2)
C2—C3—C4—C555.1 (3)C14—C15—C16—C1754.7 (3)
C3—C4—C5—C655.6 (3)C15—C16—C17—C1855.7 (3)
C7—N1—C6—C595.8 (3)C19—N2—C18—C1791.8 (3)
C7—N1—C6—C1140.0 (2)C19—N2—C18—C13143.5 (2)
C4—C5—C6—N1179.42 (18)C16—C17—C18—N2179.19 (17)
C4—C5—C6—C156.6 (2)C16—C17—C18—C1356.7 (2)
C2—C1—C6—N1177.30 (18)C14—C13—C18—N2177.45 (17)
C2—C1—C6—C557.4 (2)C14—C13—C18—C1756.9 (2)
C6—N1—C7—O23.7 (4)C18—N2—C19—O61.7 (4)
C6—N1—C7—O1176.82 (19)C18—N2—C19—O5178.42 (19)
C8—O1—C7—O26.9 (3)C20—O5—C19—O66.7 (3)
C8—O1—C7—N1172.59 (19)C20—O5—C19—N2173.15 (19)
C7—O1—C8—C1161.5 (3)C19—O5—C20—C2360.9 (3)
C7—O1—C8—C963.5 (3)C19—O5—C20—C2164.3 (3)
C7—O1—C8—C10179.4 (2)C19—O5—C20—C22178.6 (2)
C3—C2—C12—O423.3 (3)C15—C14—C24—O83.1 (3)
C1—C2—C12—O4100.9 (3)C13—C14—C24—O8122.6 (2)
C3—C2—C12—O3156.4 (2)C15—C14—C24—O7176.5 (2)
C1—C2—C12—O379.5 (3)C13—C14—C24—O757.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O60.86 (1)2.16 (1)3.009 (2)169 (2)
N2—H2A···O2i0.85 (1)2.18 (1)3.013 (2)165 (2)
O3—H3···O4ii0.821.862.672 (2)172
O7—H7···O8iii0.821.842.656 (2)171
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1; (iii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC12H21NO4
Mr243.30
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)5.854 (1), 10.000 (2), 23.014 (5)
α, β, γ (°)85.64 (2), 88.68 (2), 88.51 (2)
V3)1342.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.56 × 0.46 × 0.20
Data collection
DiffractometerBruker SMART 1K area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.767, 0.921
No. of measured, independent and
observed [I > 2σ(I)] reflections
5514, 4822, 2483
Rint0.017
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.109, 0.81
No. of reflections4822
No. of parameters324
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.17

Computer programs: SMART (Bruker, 1999), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O60.856 (9)2.163 (10)3.009 (2)169 (2)
N2—H2A···O2i0.854 (9)2.180 (11)3.013 (2)164.9 (19)
O3—H3···O4ii0.821.862.672 (2)171.5
O7—H7···O8iii0.821.842.656 (2)170.9
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1; (iii) x+1, y, z+1.
 

Acknowledgements

This work was supported by the Science Fund of the Education Office of Jiangxi, China ([2007]279).

References

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First citationBruker (1999). SMART and SAINT-Plus. Bruker AXS Inc, Madison, Wisconsin, USA.  Google Scholar
First citationHu, Y., Yu, S. L., Yang, Y. J., Zhu, J. & Deng, J. G. (2006). Chin. J. Chem. 24, 795–799.  Web of Science CrossRef CAS Google Scholar
First citationRoberts, E., Chase, T. N. & Towes, D. B. (1976). GABA in Nervous System Function. New York: Raven Press.  Google Scholar
First citationSchousboe, A. (2000). Neurochem. Res. 25, 1241–1244.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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