(R)-Methyl 2-(furan-2-carboxamido)-4-methyl­penta­noate

Xu, W.-J.; Liao, X.-J.; Xu, S.-H.; Liu, P.-R.

doi:10.1107/S1600536807036410

(R)-Methyl 2-(furan-2-carboxamido)-4-methylpentanoate

W.-J. Xu, X.-J. Liao, S.-H. Xu and P.-R. Liu

The title compound, C₁₂H₁₇NO₄, was synthesized by the condensation reaction of L-leucine methyl ester with furan-2-carbonyl chloride at room temperature. There are two molecules in the asymmetric unit. All bond lengths and angles are within normal ranges. Intermolecular N—H

O interactions link the molecules to form one-dimensional polymeric chains along the c axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036410/bx2093sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036410/bx2093Isup2.hkl Contains datablock I

CCDC reference: 657872

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R factor = 0.049
wR factor = 0.134
Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT725_ALERT_1_A D-H     Calc     0.88000, Rep     0.83000 Dev...       0.05 Ang.
              N2   -H2      1.555   1.555
PLAT726_ALERT_1_A H...A   Calc     2.36000, Rep     2.42000 Dev...       0.06 Ang.
              H2   -O5      1.555   1.555

Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C14    -   C15     ..      14.11 su

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.672
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.20
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.67 e/A   
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.74 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.11 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.43 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5     -   C13     ..       5.71 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT728_ALERT_1_C D-H..A  Calc      107.00, Rep      105.00 Dev...       2.00 Deg.
              N2   -H2   -O5      1.555   1.555   1.555

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           27.05
           From the CIF: _reflns_number_total               3189
           Count of symmetry unique reflns         3208
           Completeness (_total/calc)             99.41%
           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
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18    = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   2 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

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

Comment top

Furan derivatives are well known in many organisms (Wipf et al., 2005), and some of them are bioactive substances (Gomis-Ruth et al., 1998). In our search for bioactive compounds, a series of furan(2-carbonyl)amino acid esters, including the title compound, (I), have been synthesized by the reaction of amino acid esters with Furan-2-carbonyl chloride. We report here its crystal structure. Bond lengths and angles are unexceptional and are in good agreement with the corresponding values in (S)-Methyl 4-methyl-2-(1H-pyrrole-2-carboxamido)-pentanoate (Zeng & Liu, 2005) and 1-(4-methoxyphenyl)-3-(3-methyl-2-furan-carbonyl)-thiourea (Hritzova et al., 2005). There are two molecules in the asymmetric unit (Fig. 1) and only one kind of intermolecular hydrogen bonds in the crystal structure. Every molecule is connected with two other molecules by hydrogen-bond interactions, generating extended chains along the c axis, Figure 2.

Related literature top

For related literature, see: El-Naggar et al. (1976); Gomis-Ruth et al. (1998); Wipf & Halter (2005); Zeng & Liu (2005).

Experimental top

The synthesis of (I) was reported by El-Naggar et al.,1976. A solution of Furan-2-carbonyl chloride (0.66 g, 5 mmol) in dichloromethane (2.5 ml) was added dropwise, under stirring, to L-leucine methyl ester (0.91 g, 5 mmol) in dichloromethane (5 ml). The mixture was stirred at room temperature for 2 h and then poured into water. After filtration, the solution was wash with water(5 ml), The organic phase was dried over Na₂SO₄ and evaporated under reduced pressure. The residue was dissolved in ethanol at room temperature. Colorless orthorhombic crystals suitable for X-ray analysis (m.p. 362 K, 81.6 percent yield) grew over a period of one week when the solution was exposed to air.

Structure description top

For related literature, see: El-Naggar et al. (1976); Gomis-Ruth et al. (1998); Wipf & Halter (2005); Zeng & Liu (2005).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of the title compound.
	Fig. 2. The crystal structure of (I), viewed along the a axis. Dashed lines show N—H···O interactions. [Symmetry code: (i) -x + 1/2, -y + 1, z - 1/2]

(R)-Methyl 2-(furan-2-carboxamido)-4-methylpentanoate top

Crystal data top

C₁₂H₁₇NO₄	D_x = 1.230 Mg m⁻³
M_r = 239.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 13310 reflections
a = 8.7674 (10) Å	θ = 12–18°
b = 16.1703 (18) Å	µ = 0.09 mm⁻¹
c = 18.224 (2) Å	T = 173 K
V = 2583.6 (5) Å³	Block, colourless
Z = 8	0.50 × 0.40 × 0.20 mm
F(000) = 1024

Data collection top

Bruker SMART 1000 CCD aea-detector diffractometer	3189 independent reflections
Radiation source: fine-focus sealed tube	2685 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.1°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
T_min = 0.957, T_max = 0.982	k = −13→20
13310 measured reflections	l = −23→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.134	w = 1/[σ²(F_o²) + (0.0652P)² + 1.1602P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3189 reflections	Δρ_max = 0.67 e Å⁻³
315 parameters	Δρ_min = −0.21 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (9)

Crystal data top

C₁₂H₁₇NO₄	V = 2583.6 (5) Å³
M_r = 239.27	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.7674 (10) Å	µ = 0.09 mm⁻¹
b = 16.1703 (18) Å	T = 173 K
c = 18.224 (2) Å	0.50 × 0.40 × 0.20 mm

Data collection top

Bruker SMART 1000 CCD aea-detector diffractometer	3189 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2685 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.982	R_int = 0.024
13310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	3 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.05	Δρ_max = 0.67 e Å⁻³
3189 reflections	Δρ_min = −0.21 e Å⁻³
315 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
O1	0.1237 (3)	0.61581 (14)	0.45097 (12)	0.0445 (5)
O2	0.4018 (3)	0.58090 (14)	0.58910 (11)	0.0404 (5)
O3	0.6183 (3)	0.55287 (14)	0.44903 (13)	0.0461 (6)
O4	0.7289 (3)	0.45796 (17)	0.52091 (19)	0.0665 (9)
O5	0.2261 (3)	0.46393 (17)	0.69428 (15)	0.0632 (8)
O6	0.3297 (3)	0.56474 (14)	0.86200 (11)	0.0434 (5)
O7	0.2604 (3)	0.74834 (16)	0.72373 (15)	0.0574 (7)
O8	0.4538 (3)	0.81196 (13)	0.78045 (15)	0.0531 (7)
N1	0.3328 (3)	0.49843 (15)	0.49519 (14)	0.0319 (5)
H1	0.2638	0.4855	0.4621	0.038*
N2	0.3946 (3)	0.59578 (14)	0.74474 (13)	0.0328 (5)
H2	0.3900	0.5799	0.6986	0.039*
C1	0.2009 (3)	0.62688 (18)	0.51507 (16)	0.0336 (6)
C2	0.1566 (4)	0.6981 (2)	0.5477 (2)	0.0490 (8)
H2A	0.1927	0.7201	0.5928	0.059*
C3	0.0452 (5)	0.7331 (2)	0.5007 (3)	0.0592 (10)
H3	−0.0078	0.7837	0.5080	0.071*
C4	0.0290 (5)	0.6822 (2)	0.4449 (2)	0.0573 (10)
H4	−0.0400	0.6907	0.4054	0.069*
C5	0.3179 (3)	0.56685 (18)	0.53628 (14)	0.0305 (6)
C6	0.4648 (3)	0.44653 (18)	0.50666 (16)	0.0332 (6)
H6	0.4681	0.4293	0.5593	0.040*
C7	0.6099 (4)	0.49425 (19)	0.48859 (18)	0.0382 (7)
C8	0.8780 (5)	0.4917 (3)	0.5032 (3)	0.0790 (15)
H8A	0.8984	0.4840	0.4508	0.118*
H8B	0.9563	0.4630	0.5319	0.118*
H8C	0.8799	0.5508	0.5149	0.118*
C9	0.4580 (3)	0.36901 (17)	0.45842 (17)	0.0345 (6)
H9A	0.4396	0.3865	0.4071	0.041*
H9B	0.5590	0.3417	0.4599	0.041*
C10	0.3368 (4)	0.30551 (18)	0.47946 (16)	0.0359 (7)
H10	0.2353	0.3337	0.4812	0.043*
C11	0.3688 (5)	0.2675 (2)	0.5542 (2)	0.0537 (9)
H11A	0.2890	0.2271	0.5660	0.081*
H11B	0.3699	0.3110	0.5916	0.081*
H11C	0.4681	0.2397	0.5532	0.081*
C12	0.3321 (5)	0.2390 (2)	0.4208 (2)	0.0516 (9)
H12A	0.3141	0.2645	0.3728	0.077*
H12B	0.2495	0.2000	0.4317	0.077*
H12C	0.4296	0.2093	0.4200	0.077*
C13	0.2279 (3)	0.48155 (17)	0.76822 (17)	0.0346 (6)
C14	0.1322 (5)	0.4294 (3)	0.8043 (2)	0.0664 (12)
H14	0.1096	0.4271	0.8552	0.080*
C15	0.0722 (4)	0.3773 (2)	0.7445 (3)	0.0614 (11)
H15	0.0015	0.3333	0.7503	0.074*
C16	0.1313 (5)	0.4012 (3)	0.6822 (3)	0.0745 (13)
H16	0.1100	0.3776	0.6356	0.089*
C17	0.3217 (3)	0.55087 (17)	0.79574 (15)	0.0314 (6)
C18	0.4802 (3)	0.66905 (16)	0.76288 (15)	0.0308 (6)
H18	0.5107	0.6656	0.8157	0.037*
C19	0.3825 (4)	0.74590 (18)	0.75269 (16)	0.0362 (6)
C20	0.3752 (5)	0.8901 (2)	0.7729 (3)	0.0628 (11)
H20A	0.3565	0.9013	0.7208	0.094*
H20B	0.4381	0.9344	0.7936	0.094*
H20C	0.2777	0.8876	0.7991	0.094*
C21	0.6249 (4)	0.67787 (17)	0.71650 (17)	0.0355 (6)
H21A	0.5948	0.6845	0.6645	0.043*
H21B	0.6784	0.7291	0.7315	0.043*
C22	0.7360 (4)	0.60601 (19)	0.72204 (19)	0.0413 (7)
H22	0.6845	0.5562	0.7010	0.050*
C23	0.7791 (6)	0.5861 (3)	0.7997 (2)	0.0776 (15)
H23A	0.8320	0.6335	0.8215	0.116*
H23B	0.8467	0.5378	0.8002	0.116*
H23C	0.6869	0.5739	0.8281	0.116*
C24	0.8755 (5)	0.6246 (3)	0.6743 (3)	0.0844 (16)
H24A	0.8422	0.6378	0.6243	0.127*
H24B	0.9424	0.5761	0.6732	0.127*
H24C	0.9310	0.6718	0.6948	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0484 (13)	0.0439 (12)	0.0411 (12)	0.0026 (11)	−0.0065 (11)	0.0066 (10)
O2	0.0405 (12)	0.0506 (13)	0.0300 (10)	0.0006 (11)	−0.0022 (9)	−0.0072 (9)
O3	0.0451 (13)	0.0420 (12)	0.0511 (13)	−0.0068 (11)	0.0038 (11)	0.0067 (11)
O4	0.0329 (12)	0.0489 (14)	0.118 (2)	−0.0080 (12)	−0.0183 (15)	0.0253 (16)
O5	0.0635 (17)	0.0629 (16)	0.0634 (16)	−0.0149 (15)	−0.0060 (14)	−0.0204 (14)
O6	0.0537 (13)	0.0434 (12)	0.0330 (11)	−0.0086 (11)	0.0053 (10)	0.0030 (10)
O7	0.0539 (15)	0.0556 (14)	0.0627 (15)	0.0180 (13)	−0.0205 (13)	−0.0142 (13)
O8	0.0473 (14)	0.0269 (11)	0.0851 (18)	0.0032 (10)	−0.0039 (13)	−0.0033 (11)
N1	0.0307 (12)	0.0323 (12)	0.0326 (12)	0.0003 (10)	−0.0055 (11)	−0.0018 (10)
N2	0.0396 (13)	0.0315 (12)	0.0275 (11)	−0.0055 (11)	0.0016 (11)	−0.0014 (9)
C1	0.0308 (15)	0.0336 (14)	0.0364 (15)	−0.0043 (12)	0.0052 (12)	0.0009 (12)
C2	0.0434 (18)	0.0398 (17)	0.064 (2)	−0.0004 (15)	0.0038 (17)	−0.0098 (16)
C3	0.050 (2)	0.0391 (19)	0.088 (3)	0.0081 (16)	0.001 (2)	0.005 (2)
C4	0.056 (2)	0.052 (2)	0.064 (2)	0.0095 (19)	−0.009 (2)	0.0203 (19)
C5	0.0282 (13)	0.0360 (14)	0.0272 (13)	−0.0068 (12)	0.0046 (11)	−0.0013 (11)
C6	0.0302 (14)	0.0325 (14)	0.0370 (14)	−0.0032 (12)	−0.0031 (12)	0.0015 (13)
C7	0.0349 (15)	0.0322 (15)	0.0474 (18)	−0.0032 (13)	−0.0032 (15)	−0.0024 (13)
C8	0.036 (2)	0.067 (3)	0.134 (4)	−0.012 (2)	−0.009 (3)	0.008 (3)
C9	0.0315 (14)	0.0312 (14)	0.0409 (16)	−0.0003 (12)	0.0053 (13)	0.0010 (13)
C10	0.0330 (15)	0.0303 (14)	0.0443 (16)	−0.0028 (13)	0.0009 (13)	0.0020 (12)
C11	0.056 (2)	0.055 (2)	0.0502 (19)	−0.0210 (19)	−0.0034 (18)	0.0124 (17)
C12	0.061 (2)	0.0374 (17)	0.056 (2)	−0.0111 (17)	0.0045 (18)	−0.0041 (16)
C13	0.0312 (14)	0.0315 (14)	0.0410 (16)	0.0014 (12)	0.0004 (13)	0.0043 (12)
C14	0.046 (2)	0.070 (3)	0.084 (3)	0.0039 (19)	0.006 (2)	0.039 (2)
C15	0.0416 (19)	0.0365 (18)	0.106 (3)	−0.0111 (16)	−0.013 (2)	−0.001 (2)
C16	0.066 (3)	0.062 (3)	0.095 (3)	−0.019 (2)	−0.010 (3)	−0.020 (3)
C17	0.0326 (14)	0.0294 (13)	0.0322 (14)	0.0040 (12)	0.0036 (12)	0.0036 (12)
C18	0.0375 (15)	0.0261 (13)	0.0288 (13)	−0.0025 (12)	−0.0011 (12)	0.0007 (11)
C19	0.0389 (15)	0.0344 (15)	0.0352 (14)	0.0021 (13)	0.0013 (14)	0.0018 (12)
C20	0.066 (3)	0.0301 (16)	0.092 (3)	0.0137 (17)	0.007 (2)	0.0027 (18)
C21	0.0403 (16)	0.0269 (13)	0.0394 (15)	−0.0041 (12)	0.0001 (13)	−0.0010 (12)
C22	0.0374 (16)	0.0318 (14)	0.0548 (19)	0.0011 (13)	0.0017 (15)	−0.0077 (14)
C23	0.077 (3)	0.083 (3)	0.073 (3)	0.045 (3)	−0.029 (2)	−0.012 (2)
C24	0.059 (3)	0.067 (3)	0.127 (4)	0.006 (2)	0.041 (3)	−0.010 (3)

Geometric parameters (Å, º) top

O1—C1	1.362 (4)	C10—C12	1.517 (4)
O1—C4	1.362 (4)	C10—C11	1.521 (4)
O2—C5	1.233 (3)	C10—H10	1.0000
O3—C7	1.193 (4)	C11—H11A	0.9800
O4—C7	1.335 (4)	C11—H11B	0.9800
O4—C8	1.453 (5)	C11—H11C	0.9800
O5—C16	1.329 (5)	C12—H12A	0.9800
O5—C13	1.377 (4)	C12—H12B	0.9800
O6—C17	1.230 (3)	C12—H12C	0.9800
O7—C19	1.194 (4)	C13—C14	1.359 (5)
O8—C19	1.337 (4)	C13—C17	1.478 (4)
O8—C20	1.446 (4)	C14—C15	1.474 (5)
N1—C5	1.342 (4)	C14—H14	0.9500
N1—C6	1.444 (4)	C15—C16	1.307 (6)
N1—H1	0.8800	C15—H15	0.9500
N2—C17	1.342 (4)	C16—H16	0.9500
N2—C18	1.441 (4)	C18—C19	1.520 (4)
N2—H2	0.8800	C18—C21	1.531 (4)
C1—C2	1.353 (4)	C18—H18	1.0000
C1—C5	1.465 (4)	C20—H20A	0.9800
C2—C3	1.417 (6)	C20—H20B	0.9800
C2—H2A	0.9500	C20—H20C	0.9800
C3—C4	1.315 (6)	C21—C22	1.520 (4)
C3—H3	0.9500	C21—H21A	0.9900
C4—H4	0.9500	C21—H21B	0.9900
C6—C7	1.524 (4)	C22—C23	1.499 (5)
C6—C9	1.532 (4)	C22—C24	1.530 (5)
C6—H6	1.0000	C22—H22	1.0000
C8—H8A	0.9800	C23—H23A	0.9800
C8—H8B	0.9800	C23—H23B	0.9800
C8—H8C	0.9800	C23—H23C	0.9800
C9—C10	1.527 (4)	C24—H24A	0.9800
C9—H9A	0.9900	C24—H24B	0.9800
C9—H9B	0.9900	C24—H24C	0.9800

C1—O1—C4	105.6 (3)	C10—C12—H12B	109.5
C7—O4—C8	116.2 (3)	H12A—C12—H12B	109.5
C16—O5—C13	109.1 (3)	C10—C12—H12C	109.5
C19—O8—C20	116.1 (3)	H12A—C12—H12C	109.5
C5—N1—C6	118.4 (2)	H12B—C12—H12C	109.5
C5—N1—H1	120.8	C14—C13—O5	109.7 (3)
C6—N1—H1	120.8	C14—C13—C17	130.5 (3)
C17—N2—C18	122.3 (2)	O5—C13—C17	119.7 (3)
C17—N2—H2	118.9	C13—C14—C15	102.5 (3)
C18—N2—H2	118.9	C13—C14—H14	128.7
C2—C1—O1	110.3 (3)	C15—C14—H14	128.7
C2—C1—C5	130.5 (3)	C16—C15—C14	109.4 (3)
O1—C1—C5	119.2 (3)	C16—C15—H15	125.3
C1—C2—C3	105.8 (3)	C14—C15—H15	125.3
C1—C2—H2A	127.1	C15—C16—O5	109.2 (4)
C3—C2—H2A	127.1	C15—C16—H16	125.4
C4—C3—C2	107.0 (3)	O5—C16—H16	125.4
C4—C3—H3	126.5	O6—C17—N2	123.6 (3)
C2—C3—H3	126.5	O6—C17—C13	120.2 (3)
C3—C4—O1	111.4 (3)	N2—C17—C13	116.1 (2)
C3—C4—H4	124.3	N2—C18—C19	110.5 (2)
O1—C4—H4	124.3	N2—C18—C21	112.4 (2)
O2—C5—N1	122.0 (3)	C19—C18—C21	108.8 (2)
O2—C5—C1	120.1 (3)	N2—C18—H18	108.3
N1—C5—C1	117.9 (2)	C19—C18—H18	108.3
N1—C6—C7	110.1 (2)	C21—C18—H18	108.3
N1—C6—C9	111.2 (2)	O7—C19—O8	124.0 (3)
C7—C6—C9	108.8 (2)	O7—C19—C18	125.9 (3)
N1—C6—H6	108.9	O8—C19—C18	110.1 (2)
C7—C6—H6	108.9	O8—C20—H20A	109.5
C9—C6—H6	108.9	O8—C20—H20B	109.5
O3—C7—O4	124.6 (3)	H20A—C20—H20B	109.5
O3—C7—C6	125.8 (3)	O8—C20—H20C	109.5
O4—C7—C6	109.6 (2)	H20A—C20—H20C	109.5
O4—C8—H8A	109.5	H20B—C20—H20C	109.5
O4—C8—H8B	109.5	C22—C21—C18	115.0 (2)
H8A—C8—H8B	109.5	C22—C21—H21A	108.5
O4—C8—H8C	109.5	C18—C21—H21A	108.5
H8A—C8—H8C	109.5	C22—C21—H21B	108.5
H8B—C8—H8C	109.5	C18—C21—H21B	108.5
C10—C9—C6	115.7 (2)	H21A—C21—H21B	107.5
C10—C9—H9A	108.4	C23—C22—C21	112.9 (3)
C6—C9—H9A	108.4	C23—C22—C24	112.2 (4)
C10—C9—H9B	108.4	C21—C22—C24	108.9 (3)
C6—C9—H9B	108.4	C23—C22—H22	107.6
H9A—C9—H9B	107.4	C21—C22—H22	107.6
C12—C10—C11	110.4 (3)	C24—C22—H22	107.6
C12—C10—C9	108.6 (3)	C22—C23—H23A	109.5
C11—C10—C9	111.6 (3)	C22—C23—H23B	109.5
C12—C10—H10	108.7	H23A—C23—H23B	109.5
C11—C10—H10	108.7	C22—C23—H23C	109.5
C9—C10—H10	108.7	H23A—C23—H23C	109.5
C10—C11—H11A	109.5	H23B—C23—H23C	109.5
C10—C11—H11B	109.5	C22—C24—H24A	109.5
H11A—C11—H11B	109.5	C22—C24—H24B	109.5
C10—C11—H11C	109.5	H24A—C24—H24B	109.5
H11A—C11—H11C	109.5	C22—C24—H24C	109.5
H11B—C11—H11C	109.5	H24A—C24—H24C	109.5
C10—C12—H12A	109.5	H24B—C24—H24C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6ⁱ	0.88	2.16	2.994 (3)	159
N2—H2···O2	0.88	2.00	2.847 (3)	162
N2—H2···O5	0.83	2.42	2.751 (4)	105

Symmetry code: (i) −x+1/2, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₇NO₄
M_r	239.27
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	173
a, b, c (Å)	8.7674 (10), 16.1703 (18), 18.224 (2)
V (Å³)	2583.6 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.40 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD aea-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.957, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	13310, 3189, 2685
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.134, 1.05
No. of reflections	3189
No. of parameters	315
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.21

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.