2,6-Dimethyl-4-oxo-3-oxatri­cyclo­[5.2.1.02,6]decane-1-carboxamide

Grytsai, O.; Gorichko, M.

doi:10.1107/S1600536813017248

organic compounds

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ISSN: 2056-9890

Volume 69| Part 7| July 2013| Page o1168

https://doi.org/10.1107/S1600536813017248

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2,6-Dimethyl-4-oxo-3-oxatricyclo[5.2.1.0^2,6]decane-1-carboxamide

Oleksandr Grytsai ^a and Marian Gorichko ^a ^*

^aNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01033 Kyiv, Ukraine
^*Correspondence e-mail: 417lab@gmail.com

(Received 19 April 2013; accepted 21 June 2013; online 29 June 2013)

In the title compound, C₁₂H₁₇NO₃, which was synthesized by Wagner–Meerwein rearrangement of the N-nitroimine, the ring-junction C—C bond length is comparatively long [1.573 (2) Å] due to a steric repulsion between the methyl groups at these atoms, which also leads to an increase in the C—C—C angles along this C₄ chain [118.10 (13) and 115.04 (15) °, respectively]. In the crystal, N—H⋯O—C and N—H⋯O=C hydrogen bonds are formed between the amide group and the two O-atom acceptors of the lactone group, forming a chain along [001].

Related literature

For applications of nitroimines and their derivatives in organic synthesis, see: Squire et al. (2002 ); Bulman Page et al. (2000 ); Lalk et al. (1999 ), as organocatalysts, see: Parrott, et al. (2008 ) and in medicinal chemistry, see: Ranise et al. (1990 ); Bondavalli et al. (1987 ). For bond angles in related structures, see: Noe et al. (1996 ); Knollmuller et al. (1998 ).

Experimental

Crystal data

C₁₂H₁₇NO₃
M_r = 223.27
Triclinic, $[P \overline 1]$
a = 7.0659 (3) Å
b = 7.8206 (3) Å
c = 10.4595 (3) Å
α = 79.667 (2)°
β = 80.471 (2)°
γ = 81.579 (2)°
V = 556.69 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.25 × 0.2 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.977, T_max = 0.986
8729 measured reflections
2405 independent reflections
1754 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.141
S = 0.92
2405 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H10⋯O3ⁱ	0.91 (2)	2.17 (2)	3.065 (2)	168.7 (18)
N1—H11⋯O2ⁱⁱ	0.89 (2)	2.02 (3)	2.912 (2)	177 (2)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813017248/qm2095sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813017248/qm2095Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813017248/qm2095Isup3.cml

checkCIF report

Comment top

Nitroimines and their derivatives have found a numerous applications in organic synthesis (Squire et al., 2002; Bulman Page et al., 2000; Lalk et al., 1999), as organocatalysis (Parrott, R. W. et al., 2008) and in medicinal chemistry (Ranise et al., 1990; Bondavalli, et al., 1987). Herein, we report synthesis and crystal structure of the title compound (II), the novel 3,7-dimethyl-3-oxohexahydro-4,7-methano-2-benzofuran-4(1H)-carboxamide , C₁₂H₁₇NO₃ (Fig. 1)obtained via selective Wagner-Meerwein type rearrangement of potassium cyanide adducts of 1,7-dimethyl-2-(nitroimino)bicyclo[2.2.1]hept-7-ylacetic acid (I) (see Fig. 2).

In the structure of (II) (Fig. 1), angle deviations at Csp³ atoms range from 94.22 to 118.10 (16) °. Thus the C1—C7—C4 angle as in other previously reported compounds has a reduced value of 94.22 (12) ° (Noe et al., 1996; Knollmuller et al., 1998). Most bond distances for compound (I) were in the expected range however, the C5-C6 bond length is 1.573 (2) Å, which is apparently due to steric repulsion between the methyl groups on these atoms, this also leads to an increase in the angles C5C6C10 and C6C5C9 to 118.10 (13) and 115.04 (15) °, respectively. It is interesting to note that the bond O4—C6 is slightly longer (1.4714 (16) Å) and O4—C12 shorter (1.335 (2) Å) compared with the values previously found (average 1.45 and 1.36 Å, respectively). Intermolecular hydrogen bonds are formed through N—H···O—C and N—H···O═C between the amide and two O-atom acceptors of lactone group. (Table 1).

Related literature top

For applications of nitroimines and their derivatives in organic synthesis, see: Squire et al. (2002); Bulman Page et al. (2000); Lalk et al. (1999), as organocatalysts, see: Parrott, et al. (2008) and in medicinal chemistry, see: Ranise et al. (1990); Bondavalli et al. (1987). For bond angles in related structures, see: Noe et al. (1996); Knollmuller et al. (1998).

For related literature, see: Bondavalli et al. (1987).

Experimental top

The synthesis of the nitroimine (I) (Fig. 2) was carried out as follows. A solution of compound I (1.00 g, 4.16 mmol) in methanol (10 ml) was added to a mixture of acetone cyanohydrin 2 mmol (0.708 g) and potassium hydroxide 1.5 mmol (0.35 g) in distilled water. The resulting mixture was stirred and refluxed for 20 min. After cooling in ice an excess of 3 N aqueous hydrochloric acid was added over 5 min with vigorous stirring. Almost immediate precipitation of carboxamide was accompanied by gas (N₂O) evolution. The amide was filtered off, washed with distilled water (2x10 mL), dried in a vacuum desiccator overnight and recrystallized from absolute 2-propanol. Yield: 0.86 g 93%; m.p.: 253 °C. 1H NMR (400 MHz, [D6]DMSO, TMS, δ): 1.201 (s, 3 H), 1.516 (s, 3 H), 1.531–1.577 (m, 1 H), 1.630–1.95 (d, J=11.1Hz, 1H), 1.693–1.794 (m, 3 H), 1.952 (d, J=11.1, 1 H), 2.065 (bs, 1 H), 2.601 (s, 2 H); 13C{1H} NMR (100.70 MHz, [D6]DMSO, TMS, δ): 16.55, 20.76, 24.99, 28.53, 37.35, 44.82, 48.14, 49.56, 62.19, 97.18, 177.35,178.65; (KBr plates, cm -1): 3421.23, 3157.94, 1755.23, 1678.33.

Structure description top

For applications of nitroimines and their derivatives in organic synthesis, see: Squire et al. (2002); Bulman Page et al. (2000); Lalk et al. (1999), as organocatalysts, see: Parrott, et al. (2008) and in medicinal chemistry, see: Ranise et al. (1990); Bondavalli et al. (1987). For bond angles in related structures, see: Noe et al. (1996); Knollmuller et al. (1998).

For related literature, see: Bondavalli et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure and atom nunbering scheme for the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The synthetic route to the title compound (II).

2,6-Dimethyl-4-oxo-3-oxatricyclo[5.2.1.0^2,6]decane-1-carboxamide top

Crystal data top

C₁₂H₁₇NO₃	F(000) = 240
M_r = 223.27	D_x = 1.332 Mg m⁻³
Triclinic, P1	Melting point: 531 K
a = 7.0659 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8206 (3) Å	Cell parameters from 8729 reflections
c = 10.4595 (3) Å	θ = 2.0–27.0°
α = 79.667 (2)°	µ = 0.10 mm⁻¹
β = 80.471 (2)°	T = 296 K
γ = 81.579 (2)°	Block, colourless
V = 556.69 (4) Å³	0.25 × 0.2 × 0.15 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2405 independent reflections
Radiation source: fine-focus sealed tube	1754 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→6
T_min = 0.977, T_max = 0.986	k = −9→9
8729 measured reflections	l = −13→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2405 reflections	(Δ/σ)_max = 0.001
213 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₂H₁₇NO₃	γ = 81.579 (2)°
M_r = 223.27	V = 556.69 (4) Å³
Triclinic, P1	Z = 2
a = 7.0659 (3) Å	Mo Kα radiation
b = 7.8206 (3) Å	µ = 0.10 mm⁻¹
c = 10.4595 (3) Å	T = 296 K
α = 79.667 (2)°	0.25 × 0.2 × 0.15 mm
β = 80.471 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2405 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1754 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.986	R_int = 0.037
8729 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	Δρ_max = 0.17 e Å⁻³
2405 reflections	Δρ_min = −0.21 e Å⁻³
213 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.3999 (2)	0.54171 (18)	0.34083 (15)	0.0369 (4)
O2	0.33949 (19)	0.33578 (16)	0.51638 (12)	0.0494 (4)
O3	0.5612 (2)	0.31087 (19)	−0.04693 (13)	0.0603 (4)
O4	0.45280 (15)	0.25378 (14)	0.16493 (10)	0.0347 (3)
C1	0.1850 (2)	0.32889 (19)	0.33196 (14)	0.0273 (4)
C2	0.0143 (2)	0.2540 (2)	0.42730 (17)	0.0375 (4)
C3	−0.1362 (3)	0.2492 (3)	0.3377 (2)	0.0484 (5)
C4	−0.0303 (2)	0.3074 (2)	0.20074 (19)	0.0429 (4)
C5	0.1373 (2)	0.1653 (2)	0.16319 (15)	0.0358 (4)
C6	0.2885 (2)	0.18268 (18)	0.25359 (14)	0.0269 (3)
C7	0.0779 (3)	0.4509 (2)	0.22716 (19)	0.0381 (4)
C8	0.3163 (2)	0.4028 (2)	0.40296 (15)	0.0298 (4)
C9	0.0736 (4)	−0.0173 (3)	0.1799 (2)	0.0540 (5)
C10	0.3770 (3)	0.0174 (2)	0.33196 (19)	0.0393 (4)
C11	0.2432 (3)	0.2168 (3)	0.02428 (19)	0.0523 (5)
C12	0.4339 (3)	0.2662 (2)	0.03857 (16)	0.0404 (4)
H4	−0.113 (3)	0.340 (3)	0.133 (2)	0.060 (6)*
H21	0.057 (2)	0.134 (2)	0.4786 (17)	0.039 (5)*
H22	−0.035 (3)	0.332 (2)	0.4956 (19)	0.048 (5)*
H31	−0.255 (3)	0.336 (3)	0.358 (2)	0.064 (6)*
H32	−0.182 (3)	0.137 (3)	0.347 (2)	0.059 (6)*
H71	−0.003 (3)	0.545 (3)	0.2658 (18)	0.051 (5)*
H72	0.165 (2)	0.501 (2)	0.1515 (17)	0.035 (5)*
H91	0.027 (3)	−0.063 (3)	0.274 (2)	0.063 (6)*
H92	−0.029 (4)	−0.010 (4)	0.128 (3)	0.090 (8)*
H93	0.177 (3)	−0.102 (3)	0.143 (2)	0.068 (7)*
H101	0.470 (4)	0.049 (3)	0.379 (2)	0.070 (7)*
H102	0.277 (3)	−0.046 (3)	0.391 (2)	0.055 (6)*
H103	0.446 (3)	−0.060 (3)	0.270 (2)	0.063 (6)*
H110	0.171 (4)	0.314 (3)	−0.025 (2)	0.082 (8)*
H111	0.267 (3)	0.131 (3)	−0.027 (3)	0.078 (8)*
H10	0.397 (3)	0.577 (3)	0.253 (2)	0.054 (6)*
H11	0.479 (3)	0.583 (3)	0.383 (2)	0.059 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0469 (8)	0.0356 (8)	0.0328 (8)	−0.0195 (6)	−0.0102 (7)	−0.0014 (6)
O2	0.0690 (9)	0.0520 (8)	0.0344 (7)	−0.0301 (6)	−0.0203 (6)	0.0048 (6)
O3	0.0725 (9)	0.0650 (9)	0.0380 (8)	−0.0219 (7)	0.0160 (7)	−0.0052 (6)
O4	0.0331 (6)	0.0417 (6)	0.0298 (6)	−0.0112 (5)	0.0009 (5)	−0.0062 (5)
C1	0.0274 (7)	0.0269 (7)	0.0283 (8)	−0.0067 (6)	−0.0041 (6)	−0.0032 (6)
C2	0.0325 (8)	0.0410 (10)	0.0392 (10)	−0.0121 (7)	0.0039 (7)	−0.0087 (8)
C3	0.0284 (9)	0.0539 (12)	0.0643 (13)	−0.0113 (8)	−0.0026 (8)	−0.0118 (10)
C4	0.0378 (9)	0.0455 (10)	0.0491 (11)	−0.0073 (7)	−0.0221 (8)	−0.0013 (8)
C5	0.0419 (9)	0.0398 (9)	0.0309 (9)	−0.0144 (7)	−0.0121 (7)	−0.0051 (7)
C6	0.0284 (7)	0.0282 (7)	0.0244 (7)	−0.0103 (6)	−0.0010 (6)	−0.0019 (6)
C7	0.0376 (9)	0.0300 (8)	0.0464 (10)	−0.0018 (7)	−0.0136 (8)	−0.0005 (8)
C8	0.0334 (8)	0.0284 (7)	0.0291 (8)	−0.0060 (6)	−0.0049 (6)	−0.0066 (6)
C9	0.0637 (13)	0.0500 (12)	0.0584 (14)	−0.0241 (10)	−0.0141 (11)	−0.0167 (10)
C10	0.0441 (10)	0.0319 (9)	0.0406 (10)	−0.0016 (7)	−0.0089 (8)	−0.0016 (7)
C11	0.0651 (13)	0.0670 (14)	0.0298 (10)	−0.0192 (11)	−0.0124 (9)	−0.0069 (9)
C12	0.0536 (10)	0.0378 (9)	0.0277 (9)	−0.0099 (8)	0.0020 (8)	−0.0034 (7)

Geometric parameters (Å, º) top

N1—C8	1.326 (2)	C4—C5	1.552 (2)
N1—H10	0.91 (2)	C4—H4	0.97 (2)
N1—H11	0.89 (2)	C5—C9	1.531 (2)
O2—C8	1.2349 (19)	C5—C11	1.533 (3)
O3—C12	1.202 (2)	C5—C6	1.573 (2)
O4—C12	1.335 (2)	C6—C10	1.513 (2)
O4—C6	1.4714 (16)	C7—H71	0.97 (2)
C1—C8	1.512 (2)	C7—H72	0.979 (16)
C1—C7	1.540 (2)	C9—H91	1.00 (2)
C1—C2	1.546 (2)	C9—H92	0.97 (3)
C1—C6	1.551 (2)	C9—H93	0.99 (2)
C2—C3	1.538 (3)	C10—H101	0.97 (3)
C2—H21	1.027 (18)	C10—H102	0.99 (2)
C2—H22	1.01 (2)	C10—H103	0.98 (2)
C3—C4	1.526 (3)	C11—C12	1.492 (3)
C3—H31	1.02 (2)	C11—H110	0.96 (3)
C3—H32	0.96 (2)	C11—H111	0.91 (3)
C4—C7	1.534 (2)

C8—N1—H10	120.3 (13)	O4—C6—C1	107.26 (11)
C8—N1—H11	117.4 (14)	C10—C6—C1	116.77 (13)
H10—N1—H11	121.0 (19)	O4—C6—C5	106.01 (11)
C12—O4—C6	112.40 (12)	C10—C6—C5	118.10 (13)
C8—C1—C7	119.50 (13)	C1—C6—C5	103.22 (11)
C8—C1—C2	111.80 (12)	C4—C7—C1	94.22 (12)
C7—C1—C2	101.23 (13)	C4—C7—H71	115.3 (12)
C8—C1—C6	114.09 (12)	C1—C7—H71	109.9 (12)
C7—C1—C6	101.17 (12)	C4—C7—H72	114.6 (10)
C2—C1—C6	107.58 (12)	C1—C7—H72	113.0 (10)
C3—C2—C1	103.89 (13)	H71—C7—H72	109.2 (15)
C3—C2—H21	113.5 (10)	O2—C8—N1	122.17 (15)
C1—C2—H21	111.5 (9)	O2—C8—C1	119.81 (13)
C3—C2—H22	112.5 (11)	N1—C8—C1	118.00 (14)
C1—C2—H22	109.8 (10)	C5—C9—H91	111.8 (13)
H21—C2—H22	105.7 (14)	C5—C9—H92	108.2 (16)
C4—C3—C2	102.89 (13)	H91—C9—H92	109.9 (18)
C4—C3—H31	110.1 (12)	C5—C9—H93	112.0 (13)
C2—C3—H31	110.3 (13)	H91—C9—H93	110.3 (18)
C4—C3—H32	113.3 (13)	H92—C9—H93	104 (2)
C2—C3—H32	114.1 (13)	C6—C10—H101	108.3 (13)
H31—C3—H32	106.1 (17)	C6—C10—H102	111.6 (11)
C3—C4—C7	101.05 (15)	H101—C10—H102	112.2 (18)
C3—C4—C5	110.33 (14)	C6—C10—H103	108.2 (12)
C7—C4—C5	102.39 (13)	H101—C10—H103	108.1 (18)
C3—C4—H4	114.4 (11)	H102—C10—H103	108.2 (17)
C7—C4—H4	117.0 (12)	C12—C11—C5	107.10 (15)
C5—C4—H4	110.7 (12)	C12—C11—H110	109.9 (15)
C9—C5—C11	110.84 (16)	C5—C11—H110	111.7 (14)
C9—C5—C4	113.29 (15)	C12—C11—H111	107.6 (16)
C11—C5—C4	111.81 (16)	C5—C11—H111	115.3 (16)
C9—C5—C6	115.04 (15)	H110—C11—H111	105 (2)
C11—C5—C6	103.15 (13)	O3—C12—O4	120.98 (17)
C4—C5—C6	102.04 (12)	O3—C12—C11	127.97 (17)
O4—C6—C10	104.66 (12)	O4—C12—C11	111.04 (14)

C8—C1—C2—C3	160.01 (14)	C4—C5—C6—O4	−111.46 (12)
C7—C1—C2—C3	31.68 (16)	C9—C5—C6—C10	8.6 (2)
C6—C1—C2—C3	−73.98 (16)	C11—C5—C6—C10	−112.21 (17)
C1—C2—C3—C4	4.31 (18)	C4—C5—C6—C10	131.69 (15)
C2—C3—C4—C7	−39.09 (17)	C9—C5—C6—C1	−121.93 (16)
C2—C3—C4—C5	68.70 (18)	C11—C5—C6—C1	117.25 (14)
C3—C4—C5—C9	52.1 (2)	C4—C5—C6—C1	1.15 (14)
C7—C4—C5—C9	159.00 (16)	C3—C4—C7—C1	57.55 (14)
C3—C4—C5—C11	178.22 (15)	C5—C4—C7—C1	−56.36 (15)
C7—C4—C5—C11	−74.89 (17)	C8—C1—C7—C4	−177.35 (13)
C3—C4—C5—C6	−72.16 (15)	C2—C1—C7—C4	−54.16 (15)
C7—C4—C5—C6	34.74 (15)	C6—C1—C7—C4	56.51 (14)
C12—O4—C6—C10	119.82 (15)	C7—C1—C8—O2	150.48 (16)
C12—O4—C6—C1	−115.51 (14)	C2—C1—C8—O2	32.62 (19)
C12—O4—C6—C5	−5.73 (16)	C6—C1—C8—O2	−89.74 (17)
C8—C1—C6—O4	−54.29 (15)	C7—C1—C8—N1	−28.0 (2)
C7—C1—C6—O4	75.35 (13)	C2—C1—C8—N1	−145.89 (14)
C2—C1—C6—O4	−178.94 (11)	C6—C1—C8—N1	91.76 (16)
C8—C1—C6—C10	62.68 (18)	C9—C5—C11—C12	−125.98 (18)
C7—C1—C6—C10	−167.67 (14)	C4—C5—C11—C12	106.57 (18)
C2—C1—C6—C10	−61.96 (18)	C6—C5—C11—C12	−2.3 (2)
C8—C1—C6—C5	−165.99 (12)	C6—O4—C12—O3	−175.02 (14)
C7—C1—C6—C5	−36.34 (13)	C6—O4—C12—C11	4.3 (2)
C2—C1—C6—C5	69.37 (14)	C5—C11—C12—O3	178.28 (17)
C9—C5—C6—O4	125.45 (15)	C5—C11—C12—O4	−1.0 (2)
C11—C5—C6—O4	4.64 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O3ⁱ	0.91 (2)	2.17 (2)	3.065 (2)	168.7 (18)
N1—H11···O2ⁱⁱ	0.89 (2)	2.02 (3)	2.912 (2)	177 (2)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₇NO₃
M_r	223.27
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.0659 (3), 7.8206 (3), 10.4595 (3)
α, β, γ (°)	79.667 (2), 80.471 (2), 81.579 (2)
V (Å³)	556.69 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.2 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.977, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	8729, 2405, 1754
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.141, 0.92
No. of reflections	2405
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H10···O3ⁱ	0.91 (2)	2.17 (2)	3.065 (2)	168.7 (18)
N1—H11···O2ⁱⁱ	0.89 (2)	2.02 (3)	2.912 (2)	177 (2)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1.

References

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