tert-Butyl N-[(S)-3-isobutyl-2-oxooxetan-3-yl]carbamate

Sieroń, L.; Kudaj, A.; Olma, A.; Karolak-Wojciechowska, J.

doi:10.1107/S1600536807063866

tert-Butyl N-[(S)-3-isobutyl-2-oxooxetan-3-yl]carbamate

L. Sieroń, A. Kudaj, A. Olma and J. Karolak-Wojciechowska

The structure of the title compound, C₁₂H₂₁NO₄, contains two crystallographically independent molecules in the asymmetric unit. Molecules are linked into pseudosymmetric R₂²(8) dimers through two N—H

O hydrogen bonds. The dimers are connected by weak C—H

O interactions, resulting in a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807063866/sg2209sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807063866/sg2209Isup2.hkl Contains datablock I

CCDC reference: 676162

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.010 Å
R factor = 0.046
wR factor = 0.118
Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         94 PerFi
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C11

Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.73
PLAT113_ALERT_2_C ADDSYM Suggests Possible Pseudo/New Space-group.        P-1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C12 H21 N O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C12 H21 N O4

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               2451
           Count of symmetry unique reflns         2470
           Completeness (_total/calc)             99.23%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     ...          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C23    ...          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The discovery of a significant number of natural 2-oxetanones with very interesting biological activities has attracted much attention towards the preparation and its use as a synthetic intermediate (Yang & Romo, 1999). N-Protected-α-amino-β-lactones are useful intermediates for synthesis of β-substituted alanines via ring opening by various nucleophiles (Pansare et al., 1991). Reactions of N-Boc-α-alkylserine β-lactones with soft sulfur nucleophiles (Olma, 2004) or with sodium azide (Olma & Kudaj, 2005) yield potentially interesting building blocks for medicinal chemistry.

As part of out studies in this area, we report here the crystal structure of the title compound, (I). In the crystal structure of (I) the asymmetric unit is composed of two molecules. Pairs of these molecules are connected into pesudocentrosymmetric dimers via N–H···N hydrogen bonds, forming eight-membered rings described by the R₂²(8) graph-set motif (Etter et al., 1990) (Fig. 1). The same motif with comparable bond lengths is also observed in the structure of α-methyl analog (Smith & Goodman, 2003). The molecules in (I) differ mainly in the orientation of isobutyl substituents (Fig. 2), as indicated by torsion angles of -172.2 (6) and 85.9 (7)° for C2—C3—C5—C6 and C22—C23—C25—C26, respectively.

Related literature top

For related literature, see: Etter et al. (1990); Olma (2004); Olma & Kudaj (2005); Pansare et al. (1991); Smith & Goodman (2003); Yang & Romo (1999).

Experimental top

The title compound was synthesized by treating complex of triphenylphosphine (525 mg, 2 mmol) and diethyldiazadicarboxylate in dry tetrahydrofurane with solution of Boc-(S)-iso-butylserine (N-Boc-(S)-α-hydroxymethylleucine) in dry THF (698 mg, 2 mmol) at 0°C. After stirring 1 hr at 0°C and then 16 hrs at room temperature, THF was removed in vacuo and the crude product was purified by flash chromatography on silica gel 60 (230–400 mesh), using ethyl acetate-n-hexane (1:1) as eluent. The N-Boc-(S)-α-benzylserine lactone was obtained in 95% yield. White crystals of (I) suitable for X-ray investigation were grown from chloroform.

Structure description top

For related literature, see: Etter et al. (1990); Olma (2004); Olma & Kudaj (2005); Pansare et al. (1991); Smith & Goodman (2003); Yang & Romo (1999).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000); molecular graphics: SHELXTL (Bruker, 2000) and POV-RAY (Persistence of Vision, 2004); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. Dotted lines indicate hydrogen bonds.
	Fig. 2. A least-squares overlay of the two independent molecules of (I), fitting on the central eight atoms. H atoms have been omitted.

tert-Butyl N-[(S)-3-isobutyl-2-oxooxetan-3-yl]carbamate top

Crystal data top

C₁₂H₂₁NO₄	Z = 2
M_r = 243.30	F(000) = 264
Triclinic, P1	D_x = 1.155 Mg m⁻³
Hall symbol: P 1	Melting point = 382–383 K
a = 6.1642 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2018 (16) Å	Cell parameters from 4065 reflections
c = 11.6915 (14) Å	θ = 3.4–26.0°
α = 115.936 (14)°	µ = 0.09 mm⁻¹
β = 100.621 (10)°	T = 293 K
γ = 95.362 (11)°	Rectangular plate, colourless
V = 699.58 (19) Å³	0.25 × 0.20 × 0.10 mm

Data collection top

KUMA KM4CCD diffractometer	1367 reflections with I > 2σ(I)
Radiation source: CX-Mo12x0.4-S Seifert Mo tube	R_int = 0.032
Graphite monochromator	θ_max = 25.0°, θ_min = 3.4°
Detector resolution: 8.2356 pixels mm^-1	h = −7→7
ω scans	k = −13→12
7367 measured reflections	l = −13→13
2451 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: difference Fourier map
wR(F²) = 0.118	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.062P)²] where P = (F_o² + 2F_c²)/3
2451 reflections	(Δ/σ)_max < 0.001
317 parameters	Δρ_max = 0.12 e Å⁻³
3 restraints	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₁₂H₂₁NO₄	γ = 95.362 (11)°
M_r = 243.30	V = 699.58 (19) Å³
Triclinic, P1	Z = 2
a = 6.1642 (7) Å	Mo Kα radiation
b = 11.2018 (16) Å	µ = 0.09 mm⁻¹
c = 11.6915 (14) Å	T = 293 K
α = 115.936 (14)°	0.25 × 0.20 × 0.10 mm
β = 100.621 (10)°

Data collection top

KUMA KM4CCD diffractometer	1367 reflections with I > 2σ(I)
7367 measured reflections	R_int = 0.032
2451 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	3 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 0.96	Δρ_max = 0.12 e Å⁻³
2451 reflections	Δρ_min = −0.12 e Å⁻³
317 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	1.4399 (10)	0.1757 (5)	0.4830 (5)	0.109 (2)
O2	1.1035 (11)	0.2386 (5)	0.4645 (6)	0.142 (3)
O9	1.1871 (6)	0.1402 (4)	0.0465 (4)	0.0732 (16)
O10	1.4040 (5)	0.2338 (4)	0.2538 (3)	0.0632 (12)
N8	1.1595 (7)	0.0423 (5)	0.1767 (4)	0.0608 (17)
C2	1.2281 (16)	0.1651 (7)	0.4225 (7)	0.094 (4)
C3	1.2177 (8)	0.0381 (6)	0.3000 (5)	0.056 (2)
C4	1.4709 (10)	0.0600 (7)	0.3684 (7)	0.080 (3)
C5	1.0644 (10)	−0.0818 (6)	0.2932 (6)	0.065 (2)
C6	1.0612 (10)	−0.2220 (6)	0.1830 (6)	0.071 (2)
C7	1.2908 (11)	−0.2562 (7)	0.1790 (6)	0.084 (3)
C8	0.9089 (13)	−0.3259 (7)	0.1990 (9)	0.116 (4)
C9	1.2485 (9)	0.1394 (6)	0.1522 (6)	0.057 (2)
C11	1.5447 (9)	0.3418 (6)	0.2464 (6)	0.0630 (19)
C12	1.6836 (12)	0.2758 (8)	0.1487 (7)	0.108 (3)
C13	1.4015 (13)	0.4276 (8)	0.2093 (10)	0.129 (4)
C14	1.6964 (11)	0.4200 (7)	0.3820 (7)	0.093 (3)
O21	0.5614 (6)	−0.1756 (4)	−0.4839 (4)	0.0800 (16)
O22	0.3389 (6)	−0.0513 (4)	−0.3675 (4)	0.0866 (16)
O29	0.7503 (6)	−0.1196 (4)	−0.0326 (4)	0.0771 (17)
O30	0.5507 (5)	−0.2205 (4)	−0.2453 (3)	0.0622 (16)
N28	0.8048 (6)	−0.0325 (4)	−0.1694 (4)	0.0567 (17)
C22	0.5175 (10)	−0.0792 (7)	−0.3759 (6)	0.066 (3)
C23	0.7590 (8)	−0.0328 (6)	−0.2933 (6)	0.052 (2)
C24	0.7917 (9)	−0.1606 (6)	−0.4128 (6)	0.071 (2)
C25	0.8812 (9)	0.0973 (5)	−0.2828 (6)	0.058 (2)
C26	0.8569 (10)	0.2326 (6)	−0.1764 (6)	0.067 (2)
C27	0.6166 (11)	0.2527 (7)	−0.1836 (7)	0.091 (3)
C28	1.0010 (13)	0.3476 (7)	−0.1818 (8)	0.104 (3)
C29	0.7063 (9)	−0.1247 (6)	−0.1397 (6)	0.055 (2)
C31	0.3953 (9)	−0.3211 (6)	−0.2350 (6)	0.063 (2)
C32	0.2568 (11)	−0.2483 (9)	−0.1438 (8)	0.107 (3)
C33	0.5216 (11)	−0.4104 (8)	−0.1981 (9)	0.108 (3)
C34	0.2499 (10)	−0.3999 (7)	−0.3762 (6)	0.091 (3)
H4A	1.50880	−0.01380	0.38540	0.0960*
H4B	1.57410	0.08380	0.32490	0.0960*
H5A	1.10960	−0.08350	0.37640	0.0780*
H5B	0.91190	−0.06560	0.28400	0.0780*
H6	0.99370	−0.22450	0.09910	0.0850*
H7A	1.36120	−0.25310	0.26080	0.1260*
H7B	1.38140	−0.19170	0.16490	0.1260*
H7C	1.27650	−0.34540	0.10860	0.1260*
H8	1.05900	−0.02320	0.11360	0.0730*
H8A	0.90490	−0.41500	0.13110	0.1740*
H8B	0.75960	−0.30710	0.19250	0.1740*
H8C	0.96630	−0.32100	0.28330	0.1740*
H12A	1.74390	0.20690	0.16460	0.1610*
H12B	1.80490	0.34300	0.15920	0.1610*
H12C	1.58960	0.23580	0.06080	0.1610*
H13A	1.30920	0.37430	0.12130	0.1930*
H13B	1.49690	0.50330	0.21410	0.1930*
H13C	1.30720	0.45980	0.26880	0.1930*
H14A	1.60960	0.43350	0.44550	0.1400*
H14B	1.76670	0.50620	0.39410	0.1400*
H14C	1.80990	0.37030	0.39360	0.1400*
H24A	0.90530	−0.14110	−0.45310	0.0860*
H24B	0.81610	−0.23510	−0.39400	0.0860*
H25A	0.83120	0.09650	−0.36690	0.0700*
H25B	1.04040	0.09470	−0.27000	0.0700*
H26	0.91720	0.23590	−0.09120	0.0800*
H27A	0.55490	0.25370	−0.26470	0.1370*
H27B	0.61350	0.33720	−0.11110	0.1370*
H27C	0.52870	0.17990	−0.17940	0.1370*
H28	0.90560	0.03320	−0.10670	0.0680*
H28A	0.94980	0.34450	−0.26590	0.1560*
H28B	1.15540	0.33770	−0.16910	0.1560*
H28C	0.98850	0.43280	−0.11380	0.1560*
H32A	0.14490	−0.31310	−0.14260	0.1600*
H32B	0.18430	−0.19110	−0.17350	0.1600*
H32C	0.35230	−0.19400	−0.05690	0.1600*
H33A	0.63820	−0.43120	−0.24390	0.1630*
H33B	0.42080	−0.49270	−0.22130	0.1630*
H33C	0.58780	−0.36520	−0.10510	0.1630*
H34A	0.34100	−0.44600	−0.43350	0.1370*
H34B	0.18640	−0.33820	−0.40280	0.1370*
H34C	0.13090	−0.46490	−0.38080	0.1370*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.150 (5)	0.095 (4)	0.059 (3)	−0.023 (3)	−0.016 (3)	0.040 (3)
O2	0.215 (6)	0.089 (3)	0.128 (4)	0.045 (4)	0.085 (4)	0.038 (3)
O9	0.078 (2)	0.077 (3)	0.055 (3)	−0.016 (2)	−0.014 (2)	0.040 (2)
O10	0.064 (2)	0.063 (2)	0.052 (2)	−0.014 (2)	−0.005 (2)	0.030 (2)
N8	0.066 (3)	0.060 (3)	0.055 (3)	−0.011 (2)	−0.008 (2)	0.039 (3)
C2	0.149 (8)	0.068 (5)	0.081 (6)	0.021 (5)	0.033 (5)	0.048 (4)
C3	0.070 (4)	0.058 (4)	0.037 (3)	0.007 (3)	0.006 (3)	0.024 (3)
C4	0.091 (5)	0.077 (4)	0.071 (4)	0.000 (4)	−0.007 (3)	0.048 (4)
C5	0.077 (4)	0.070 (4)	0.066 (4)	0.014 (3)	0.023 (3)	0.046 (4)
C6	0.080 (4)	0.064 (4)	0.071 (4)	0.006 (3)	0.005 (3)	0.040 (4)
C7	0.112 (5)	0.079 (4)	0.073 (4)	0.032 (4)	0.028 (4)	0.042 (4)
C8	0.125 (6)	0.072 (4)	0.158 (8)	−0.008 (4)	0.036 (5)	0.064 (5)
C9	0.050 (3)	0.068 (4)	0.048 (4)	0.001 (3)	−0.006 (3)	0.033 (4)
C11	0.062 (3)	0.049 (3)	0.071 (4)	−0.006 (3)	0.004 (3)	0.030 (3)
C12	0.097 (5)	0.123 (6)	0.097 (6)	−0.009 (5)	0.037 (4)	0.046 (5)
C13	0.108 (6)	0.082 (5)	0.203 (10)	0.003 (5)	−0.002 (6)	0.091 (6)
C14	0.095 (5)	0.075 (4)	0.080 (5)	−0.023 (4)	0.001 (4)	0.027 (4)
O21	0.087 (3)	0.089 (3)	0.041 (2)	0.005 (2)	0.007 (2)	0.016 (2)
O22	0.063 (2)	0.100 (3)	0.093 (3)	0.014 (2)	0.004 (2)	0.048 (2)
O29	0.086 (3)	0.082 (3)	0.061 (3)	−0.016 (2)	−0.014 (2)	0.050 (3)
O30	0.063 (2)	0.063 (3)	0.053 (3)	−0.010 (2)	−0.002 (2)	0.031 (2)
N28	0.060 (3)	0.053 (3)	0.050 (3)	−0.008 (2)	−0.006 (2)	0.029 (2)
C22	0.056 (4)	0.089 (5)	0.065 (4)	0.012 (3)	0.008 (3)	0.050 (4)
C23	0.042 (3)	0.061 (4)	0.058 (4)	0.002 (3)	0.006 (3)	0.035 (3)
C24	0.060 (3)	0.082 (4)	0.054 (4)	0.007 (3)	0.011 (3)	0.019 (3)
C25	0.059 (3)	0.064 (4)	0.055 (4)	0.008 (3)	0.013 (3)	0.032 (3)
C26	0.077 (4)	0.064 (4)	0.070 (4)	0.011 (3)	0.014 (3)	0.043 (3)
C27	0.094 (5)	0.094 (5)	0.077 (5)	0.032 (4)	0.018 (3)	0.031 (4)
C28	0.123 (6)	0.074 (5)	0.112 (6)	−0.001 (4)	0.029 (4)	0.044 (4)
C29	0.056 (4)	0.047 (4)	0.055 (4)	−0.001 (3)	−0.002 (3)	0.027 (4)
C31	0.047 (3)	0.072 (4)	0.067 (4)	−0.003 (3)	0.008 (3)	0.035 (4)
C32	0.078 (5)	0.151 (7)	0.086 (5)	0.010 (5)	0.029 (4)	0.050 (5)
C33	0.084 (4)	0.090 (5)	0.157 (7)	0.000 (4)	−0.012 (5)	0.082 (5)
C34	0.066 (4)	0.085 (5)	0.083 (5)	−0.013 (4)	−0.002 (4)	0.017 (4)

Geometric parameters (Å, º) top

O1—C2	1.333 (11)	C12—H12A	0.96
O1—C4	1.461 (9)	C12—H12B	0.96
O2—C2	1.189 (12)	C12—H12C	0.96
O9—C9	1.228 (8)	C13—H13B	0.96
O10—C9	1.319 (7)	C13—H13A	0.96
O10—C11	1.465 (8)	C13—H13C	0.96
O21—C22	1.350 (8)	C14—H14B	0.96
O21—C24	1.460 (7)	C14—H14C	0.96
O22—C22	1.182 (8)	C14—H14A	0.96
O29—C29	1.206 (8)	C22—C23	1.518 (8)
O30—C31	1.470 (8)	C23—C24	1.565 (9)
O30—C29	1.345 (7)	C23—C25	1.520 (10)
N8—C3	1.443 (7)	C25—C26	1.526 (9)
N8—C9	1.336 (9)	C26—C27	1.512 (9)
N8—H8	0.8600	C26—C28	1.527 (11)
N28—C23	1.422 (8)	C31—C33	1.481 (12)
N28—C29	1.353 (9)	C31—C34	1.530 (9)
N28—H28	0.8600	C31—C32	1.495 (10)
C2—C3	1.499 (10)	C24—H24A	0.97
C3—C5	1.531 (10)	C24—H24B	0.97
C3—C4	1.560 (8)	C25—H25A	0.97
C5—C6	1.530 (9)	C25—H25B	0.97
C6—C8	1.524 (11)	C26—H26	0.98
C6—C7	1.504 (10)	C27—H27A	0.96
C11—C14	1.497 (9)	C27—H27B	0.96
C11—C13	1.508 (12)	C27—H27C	0.96
C11—C12	1.525 (10)	C28—H28A	0.96
C4—H4B	0.97	C28—H28B	0.96
C4—H4A	0.97	C28—H28C	0.96
C5—H5B	0.97	C32—H32A	0.96
C5—H5A	0.97	C32—H32B	0.96
C6—H6	0.98	C32—H32C	0.96
C7—H7A	0.96	C33—H33A	0.96
C7—H7C	0.96	C33—H33B	0.96
C7—H7B	0.96	C33—H33C	0.96
C8—H8B	0.96	C34—H34A	0.96
C8—H8C	0.96	C34—H34B	0.96
C8—H8A	0.96	C34—H34C	0.96

C2—O1—C4	92.1 (5)	H14A—C14—H14B	109
C9—O10—C11	122.9 (5)	C11—C14—H14A	109
C22—O21—C24	91.9 (4)	H14B—C14—H14C	110
C29—O30—C31	121.5 (4)	C11—C14—H14B	110
C3—N8—C9	125.5 (5)	C11—C14—H14C	109
C3—N8—H8	117	O21—C22—O22	125.3 (6)
C9—N8—H8	117	O22—C22—C23	139.1 (6)
C23—N28—C29	126.8 (5)	O21—C22—C23	95.6 (5)
C23—N28—H28	117	N28—C23—C24	116.9 (6)
C29—N28—H28	117	N28—C23—C22	118.4 (5)
O1—C2—C3	96.4 (7)	C22—C23—C25	114.2 (6)
O1—C2—O2	126.8 (7)	N28—C23—C25	111.0 (5)
O2—C2—C3	136.8 (8)	C22—C23—C24	81.9 (5)
N8—C3—C4	119.1 (5)	C24—C23—C25	111.6 (5)
C2—C3—C5	110.7 (5)	O21—C24—C23	89.3 (4)
N8—C3—C5	109.9 (5)	C23—C25—C26	118.8 (5)
N8—C3—C2	117.4 (6)	C25—C26—C28	109.3 (5)
C4—C3—C5	115.0 (6)	C25—C26—C27	114.1 (5)
C2—C3—C4	82.3 (5)	C27—C26—C28	110.6 (6)
O1—C4—C3	88.8 (5)	O29—C29—N28	124.3 (6)
C3—C5—C6	116.7 (5)	O29—C29—O30	125.2 (6)
C5—C6—C8	107.9 (6)	O30—C29—N28	110.5 (5)
C7—C6—C8	111.0 (6)	O30—C31—C33	110.2 (5)
C5—C6—C7	113.8 (5)	O30—C31—C34	101.3 (5)
O9—C9—O10	124.5 (6)	C32—C31—C34	110.5 (5)
O9—C9—N8	122.8 (6)	C33—C31—C34	110.5 (6)
O10—C9—N8	112.8 (5)	C32—C31—C33	114.9 (7)
C12—C11—C14	109.6 (5)	O30—C31—C32	108.6 (6)
O10—C11—C14	103.5 (5)	O21—C24—H24A	114
C12—C11—C13	112.7 (6)	O21—C24—H24B	114
C13—C11—C14	112.1 (7)	C23—C24—H24A	114
O10—C11—C13	110.6 (5)	C23—C24—H24B	114
O10—C11—C12	107.8 (6)	H24A—C24—H24B	111
C3—C4—H4A	114	C23—C25—H25A	108
C3—C4—H4B	114	C23—C25—H25B	108
O1—C4—H4B	114	C26—C25—H25A	108
O1—C4—H4A	114	C26—C25—H25B	108
H4A—C4—H4B	111	H25A—C25—H25B	107
H5A—C5—H5B	107	C25—C26—H26	107
C6—C5—H5B	108	C27—C26—H26	108
C3—C5—H5A	108	C28—C26—H26	108
C6—C5—H5A	108	C26—C27—H27A	110
C3—C5—H5B	108	C26—C27—H27B	109
C7—C6—H6	108	C26—C27—H27C	109
C8—C6—H6	108	H27A—C27—H27B	110
C5—C6—H6	108	H27A—C27—H27C	109
C6—C7—H7C	109	H27B—C27—H27C	109
C6—C7—H7A	110	C26—C28—H28A	109
H7A—C7—H7B	109	C26—C28—H28B	109
H7B—C7—H7C	109	C26—C28—H28C	109
H7A—C7—H7C	110	H28A—C28—H28B	109
C6—C7—H7B	109	H28A—C28—H28C	110
C6—C8—H8A	109	H28B—C28—H28C	109
C6—C8—H8B	109	C31—C32—H32A	109
H8B—C8—H8C	110	C31—C32—H32B	109
H8A—C8—H8B	109	C31—C32—H32C	109
C6—C8—H8C	109	H32A—C32—H32B	110
H8A—C8—H8C	109	H32A—C32—H32C	110
C11—C12—H12B	110	H32B—C32—H32C	109
C11—C12—H12C	110	C31—C33—H33A	110
C11—C12—H12A	109	C31—C33—H33B	109
H12A—C12—H12B	109	C31—C33—H33C	109
H12A—C12—H12C	109	H33A—C33—H33B	109
H12B—C12—H12C	109	H33A—C33—H33C	109
C11—C13—H13C	109	H33B—C33—H33C	109
H13A—C13—H13B	109	C31—C34—H34A	110
H13A—C13—H13C	109	C31—C34—H34B	109
C11—C13—H13B	109	C31—C34—H34C	109
H13B—C13—H13C	109	H34A—C34—H34B	109
C11—C13—H13A	109	H34A—C34—H34C	109
H14A—C14—H14C	109	H34B—C34—H34C	109

C4—O1—C2—O2	−176.6 (9)	O1—C2—C3—C5	109.5 (6)
C4—O1—C2—C3	4.7 (6)	O2—C2—C3—C5	−69.0 (12)
C2—O1—C4—C3	−4.5 (6)	O1—C2—C3—N8	−123.3 (6)
C11—O10—C9—O9	−8.8 (9)	O2—C2—C3—C4	177.1 (11)
C11—O10—C9—N8	172.5 (5)	O2—C2—C3—N8	58.2 (13)
C9—O10—C11—C12	−62.4 (7)	N8—C3—C5—C6	56.6 (7)
C9—O10—C11—C13	61.2 (8)	C4—C3—C5—C6	−81.1 (7)
C9—O10—C11—C14	−178.5 (5)	C2—C3—C5—C6	−172.2 (6)
C22—O21—C24—C23	−8.8 (5)	N8—C3—C4—O1	121.1 (6)
C24—O21—C22—O22	−172.7 (8)	C2—C3—C4—O1	4.0 (5)
C24—O21—C22—C23	9.1 (6)	C5—C3—C4—O1	−105.3 (6)
C31—O30—C29—O29	8.2 (9)	C3—C5—C6—C8	177.1 (6)
C31—O30—C29—N28	−170.7 (5)	C3—C5—C6—C7	53.4 (8)
C29—O30—C31—C32	61.1 (7)	O22—C22—C23—C24	173.7 (11)
C29—O30—C31—C33	−65.5 (7)	O22—C22—C23—C25	−76.2 (12)
C29—O30—C31—C34	177.5 (5)	O21—C22—C23—N28	−124.8 (6)
C9—N8—C3—C2	47.2 (8)	O21—C22—C23—C24	−8.6 (5)
C3—N8—C9—O9	−177.5 (5)	O21—C22—C23—C25	101.5 (6)
C3—N8—C9—O10	1.3 (8)	O22—C22—C23—N28	57.4 (14)
C9—N8—C3—C4	−49.5 (9)	N28—C23—C24—O21	125.8 (5)
C9—N8—C3—C5	174.8 (5)	N28—C23—C25—C26	−51.2 (7)
C29—N28—C23—C25	172.4 (5)	C22—C23—C25—C26	85.9 (7)
C23—N28—C29—O30	−0.8 (8)	C24—C23—C25—C26	176.6 (5)
C29—N28—C23—C24	−58.1 (7)	C25—C23—C24—O21	−105.0 (5)
C23—N28—C29—O29	−179.6 (6)	C22—C23—C24—O21	7.9 (5)
C29—N28—C23—C22	37.4 (9)	C23—C25—C26—C28	177.8 (6)
O1—C2—C3—C4	−4.4 (6)	C23—C25—C26—C27	−57.9 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O29	0.86	2.12	2.937 (6)	158
N28—H28···O9	0.86	2.06	2.890 (6)	162
C12—H12C···O9	0.96	2.55	3.049 (9)	112
C13—H13A···O9	0.96	2.36	2.941 (11)	118
C27—H27C···O22	0.96	2.53	3.209 (9)	127
C32—H32C···O29	0.96	2.44	3.018 (9)	119

Experimental details

Crystal data
Chemical formula	C₁₂H₂₁NO₄
M_r	243.30
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.1642 (7), 11.2018 (16), 11.6915 (14)
α, β, γ (°)	115.936 (14), 100.621 (10), 95.362 (11)
V (Å³)	699.58 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.10

Data collection
Diffractometer	KUMA KM4CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7367, 2451, 1367
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.118, 0.96
No. of reflections	2451
No. of parameters	317
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.12

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXTL (Bruker, 2000) and POV-RAY (Persistence of Vision, 2004), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O29	0.86	2.12	2.937 (6)	158
N28—H28···O9	0.86	2.06	2.890 (6)	162
C12—H12C···O9	0.96	2.55	3.049 (9)	112
C13—H13A···O9	0.96	2.36	2.941 (11)	118
C27—H27C···O22	0.96	2.53	3.209 (9)	127
C32—H32C···O29	0.96	2.44	3.018 (9)	119

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