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The title compound, C15H18N2O4, was synthesized by the triphosgenation of ethanol and N-butyl-4-amino­phthal­imide. There are two independent mol­ecules in the asymmetric unit, which are linked into chains by N—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803009346/tk6100sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803009346/tk6100Isup2.hkl
Contains datablock I

CCDC reference: 214647

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.062
  • wR factor = 0.168
  • Data-to-parameter ratio = 12.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.808 1.000 Tmin' and Tmax expected: 0.972 0.993 RR' = 0.825 Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Organic carbamates are valuable synthetic intermediates, and are ubiquitously found in a variety of biologically active compounds (Vauthey et al., 2000). Functionalization of the carbamate moiety offers an attractive method for the generation of derivatives which may constitute interesting medicinal and biological properties (Folkmann et al., 1990). We are interested in phthalimide derivatives and a search of the literature revealed that some phthalimide derivatives had cytotoxicity (Hall et al., 1995) and anti-HIV activity (Van Derpoorten et al., 1997). It was assumed that compounds having both phthalimide and carbamate residues in one molecule may possess some attractive biological activities. In this connection, the structure of the title compound, ethyl N-(2-butyl-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)carbamate, (I), is reported.

There are two independent molecules of (I) comprising the asymmetric unit and all molecules are connected into a chain via N—H···O contacts: H···O 2.15 Å, N···O 2.985 (16) Å and N—H···O 163° for N2—H···O6; H···O 2.11 Å, N···O 2.947 (16) Å and N—H···O 163° for N4—H···O2i [symmetry code: (i) x, −1 + y, z] (Fig. 1 and Table 1). This arrangement is similar to that found for phthalimide (Zakaria et al., 2002). The phthalimide group is planar, with the mean deviation from the least-squares plane being 0.005 (3) Å [0.015 (4) Å for the second independent molecule]. This observation is diferent from the related N-(3-iodopropyl)phthalimide moiety which is not exactly planar (Chandramohan et al., 2000). The carbamate moiety is effectively planar, as reflected in the mean deviation of the atoms from this plane of 0.002 (3) Å [0.001 (3) Å], in good agreement with the corresponding data for ethyl N-(3-oxobutanoyl)carbamate (Golden et al., 2002). The dihedral angle between the mean planes of the phthalimide and carbamate moieties is 5.7 (3) and 5.9 (3)°, respectively. The n-butyl moieties (C1/C2/C3/C4 and C16/C17/C18/C19) and phthalimide groups are folded towards each other, making an dihedral angle of 106.4 (2)° [101.7 (2)°], which is somewhat different from the corresponding angles found in the N-(3-iodopropyl)phthalimide structure of 76.6 (2)° (Chandramohan et al., 2000).

Experimental top

N-Butyl-4-aminophthalimide (12 mmol) and triethylamine (12 mmol) in dry chloroform (30 ml) were placed in a 50 ml flask equipped with an N2 inlet adaptor and a rubber septum, and the mixture was cooled to 263 K with stirring. Triphosgene (4 mmol) in chloroform was added dropwise and the resulting mixture was stirred at 273 K for 3 h and at 293 K for an additional 2 h. The solvent was then evaporated in vacuo to give (2-butyl-1,3-dioxo-2,3-dihydro-1H-isoindole-5-yl)carbamic chloride, (II). (II) was soluted in dry ethanol (20 ml) and stirring at room temperature for 2 h. After evaporation of the surplus ethanol, the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 10:1) to give the title compound, (I). M.p. 413–415 K; IR (KBr): 3340 (N—H), 3080, 2951 (C—H), 1730, 1697 (CO) cm−1; 1H NMR (CDCl3, p.p.m.): 0.92 (3H, t), 1.27–1.43 (5H, m), 1.62 (2H, s), 3.63 (2H, t), 4.24 (2H, m), 6.98 (1H, s), 7.72 (2H, m), 7.85 (1H, s). (I) (50 mg) was dissolved in ethyl acetate (15 ml) and the solution was kept at room temperature for 4 d to give colorless single crystals.

Refinement top

All H atoms were included in the riding-model approximation with Uiso = 1.2Ueq for CH2 and 1.5Ueq for CH3. The terminal ethyl groups in the carbamate residues were found to be disorderd. There are two components of the disorder, each with unequal partial occupancies of 0.77 and 0.23 in the first molecule, and 0.52 and 0.48 in the second. The distances C14—C15, C14'—C15', C29—C30 and C29'—C30' were fixed at 1.54 Å and C14—O4, C14'—O4', C29—O8 and C29'—O8' were fixed at 1.45 Å.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Unit-cell contents of (I) showing H-bonding interactions and the atomic numbering scheme.
Ethyl N-(2-butyl-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)carbamate top
Crystal data top
C15H18N2O4Z = 4
Mr = 290.31F(000) = 616
Triclinic, P1Dx = 1.275 Mg m3
a = 6.933 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.210 (4) ÅCell parameters from 936 reflections
c = 15.913 (5) Åθ = 2.8–23.1°
α = 99.657 (6)°µ = 0.09 mm1
β = 101.373 (6)°T = 293 K
γ = 91.120 (6)°Plate, colorless
V = 1512.8 (8) Å30.30 × 0.20 × 0.08 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5277 independent reflections
Radiation source: fine-focus sealed tube2549 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ϕ and ω scansθmax = 25.1°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 78
Tmin = 0.808, Tmax = 1.000k = 1116
7713 measured reflectionsl = 1818
Refinement top
Refinement on F2144 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062 w = 1/[σ2(Fo2) + (0.084P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.168(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.30 e Å3
5277 reflectionsΔρmin = 0.31 e Å3
418 parameters
Crystal data top
C15H18N2O4γ = 91.120 (6)°
Mr = 290.31V = 1512.8 (8) Å3
Triclinic, P1Z = 4
a = 6.933 (2) ÅMo Kα radiation
b = 14.210 (4) ŵ = 0.09 mm1
c = 15.913 (5) ÅT = 293 K
α = 99.657 (6)°0.30 × 0.20 × 0.08 mm
β = 101.373 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5277 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
2549 reflections with I > 2σ(I)
Tmin = 0.808, Tmax = 1.000Rint = 0.035
7713 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.062144 restraints
wR(F2) = 0.168H-atom parameters constrained
S = 1.03Δρmax = 0.30 e Å3
5277 reflectionsΔρmin = 0.31 e Å3
418 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*/UeqOcc. (<1)
O10.2078 (4)0.74190 (18)0.65282 (16)0.0753 (8)
O20.2449 (4)1.05357 (18)0.61838 (18)0.0852 (9)
O30.2613 (5)0.7533 (2)0.19331 (17)0.0892 (10)
O40.2792 (4)0.59472 (19)0.18682 (15)0.0713 (8)
O50.3010 (4)0.18798 (17)0.36444 (16)0.0729 (8)
O60.2679 (4)0.51277 (17)0.40089 (17)0.0765 (8)
O70.2139 (4)0.3674 (2)0.82189 (17)0.0822 (9)
O80.2318 (4)0.2111 (2)0.83008 (16)0.0833 (9)
N10.2251 (5)0.9050 (2)0.65709 (19)0.0633 (9)
N20.2604 (4)0.6823 (2)0.31219 (18)0.0569 (8)
H2C0.25910.62660.32660.068*
N30.2910 (4)0.3499 (2)0.36153 (18)0.0564 (8)
N40.2387 (4)0.2537 (2)0.70447 (18)0.0594 (8)
H4C0.24570.19290.69040.071*
C10.7594 (9)0.9999 (4)0.8653 (4)0.141 (2)
H1A0.85551.04340.85440.211*
H1B0.80820.93680.86090.211*
H1C0.73481.02020.92270.211*
C20.5683 (8)0.9986 (3)0.7983 (3)0.0958 (15)
H2A0.52171.06280.80230.115*
H2B0.59510.97960.74050.115*
C30.4107 (8)0.9328 (3)0.8102 (3)0.0899 (15)
H3A0.39170.94890.86960.108*
H3B0.45450.86800.80220.108*
C40.2146 (7)0.9352 (3)0.7488 (3)0.0796 (13)
H4A0.11830.89380.76350.096*
H4B0.16990.99980.75670.096*
C50.2223 (5)0.8104 (3)0.6169 (2)0.0568 (10)
C60.2372 (5)0.8119 (2)0.5262 (2)0.0479 (9)
C70.2408 (5)0.7379 (2)0.4594 (2)0.0505 (9)
H7A0.23380.67480.46760.061*
C80.2551 (5)0.7598 (2)0.3785 (2)0.0494 (9)
C90.2647 (5)0.8548 (3)0.3670 (2)0.0625 (11)
H9A0.27310.86860.31270.075*
C100.2618 (6)0.9289 (3)0.4355 (2)0.0652 (11)
H10A0.26880.99220.42770.078*
C110.2482 (5)0.9068 (2)0.5154 (2)0.0541 (9)
C120.2405 (6)0.9670 (3)0.5997 (3)0.0627 (10)
C130.2672 (6)0.6844 (3)0.2283 (2)0.0631 (10)
C140.336 (5)0.5752 (16)0.1028 (12)0.089 (10)0.23 (2)
H14A0.47200.55750.10930.107*0.23 (2)
H14B0.32140.63080.07450.107*0.23 (2)
C150.196 (5)0.492 (3)0.050 (2)0.102 (10)0.23 (2)
H15A0.20390.48490.01050.153*0.23 (2)
H15B0.06340.50440.05580.153*0.23 (2)
H15C0.23290.43380.07080.153*0.23 (2)
C14'0.2600 (18)0.5866 (4)0.0916 (3)0.072 (2)0.77 (2)
H14C0.35580.62980.07860.087*0.77 (2)
H14D0.12910.60220.06490.087*0.77 (2)
C15'0.297 (2)0.4850 (5)0.0585 (6)0.091 (3)0.77 (2)
H15D0.28660.47590.00340.137*0.77 (2)
H15E0.20060.44330.07180.137*0.77 (2)
H15F0.42620.47060.08590.137*0.77 (2)
C160.2171 (9)0.3378 (5)0.1388 (4)0.144 (2)
H16A0.31980.38170.14270.216*
H16B0.26030.27680.14890.216*
H16C0.18680.33060.08180.216*
C170.0326 (7)0.3764 (3)0.2074 (3)0.0890 (14)
H17A0.00780.43890.19780.107*
H17B0.06480.38440.26470.107*
C180.1357 (7)0.3124 (3)0.2052 (3)0.0805 (13)
H18A0.16770.30500.14790.097*
H18B0.09380.24980.21390.097*
C190.3203 (6)0.3477 (3)0.2728 (2)0.0711 (12)
H19A0.42600.30620.26270.085*
H19B0.35990.41150.26620.085*
C200.2861 (5)0.2690 (3)0.3999 (2)0.0550 (9)
C210.2629 (5)0.3043 (2)0.4906 (2)0.0468 (9)
C220.2584 (5)0.2547 (2)0.5569 (2)0.0500 (9)
H22A0.26700.18860.54860.060*
C230.2406 (5)0.3068 (2)0.6378 (2)0.0492 (9)
C240.2264 (5)0.4055 (2)0.6486 (2)0.0571 (10)
H24A0.21290.43930.70230.069*
C250.2320 (5)0.4540 (2)0.5804 (2)0.0585 (10)
H25A0.22350.52010.58790.070*
C260.2503 (5)0.4026 (2)0.5012 (2)0.0512 (9)
C270.2696 (5)0.4326 (3)0.4189 (2)0.0567 (10)
C280.2273 (6)0.2862 (3)0.7881 (2)0.0635 (10)
C290.1836 (18)0.2220 (11)0.9163 (6)0.085 (5)0.528 (18)
H29A0.07650.17770.91760.102*0.528 (18)
H29B0.15040.28680.93630.102*0.528 (18)
C300.381 (2)0.1972 (14)0.9700 (8)0.123 (5)0.528 (18)
H30A0.37360.20491.03030.185*0.528 (18)
H30B0.48550.23900.96330.185*0.528 (18)
H30C0.40760.13210.94960.185*0.528 (18)
C29'0.254 (3)0.2426 (8)0.9266 (5)0.072 (4)0.472 (18)
H29C0.13830.27490.93950.087*0.472 (18)
H29D0.36870.28610.94950.087*0.472 (18)
C30'0.276 (3)0.1531 (8)0.9663 (8)0.099 (5)0.472 (18)
H30D0.27930.16911.02760.148*0.472 (18)
H30E0.39680.12490.95720.148*0.472 (18)
H30F0.16700.10850.93930.148*0.472 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.112 (2)0.0555 (16)0.0669 (18)0.0036 (15)0.0308 (16)0.0200 (14)
O20.129 (3)0.0428 (16)0.087 (2)0.0120 (16)0.0293 (18)0.0103 (14)
O30.140 (3)0.0706 (19)0.0563 (17)0.0100 (18)0.0121 (17)0.0207 (15)
O40.093 (2)0.0732 (19)0.0501 (16)0.0037 (15)0.0216 (14)0.0082 (14)
O50.109 (2)0.0485 (16)0.0622 (17)0.0231 (14)0.0222 (15)0.0050 (13)
O60.107 (2)0.0474 (16)0.0833 (19)0.0077 (14)0.0313 (16)0.0212 (14)
O70.114 (2)0.0688 (19)0.0608 (18)0.0134 (16)0.0187 (16)0.0005 (15)
O80.127 (3)0.0767 (19)0.0534 (17)0.0236 (17)0.0289 (17)0.0169 (15)
N10.087 (2)0.0477 (19)0.061 (2)0.0043 (16)0.0295 (18)0.0095 (16)
N20.071 (2)0.0537 (18)0.0481 (19)0.0008 (15)0.0146 (16)0.0138 (15)
N30.069 (2)0.0499 (18)0.0546 (19)0.0116 (15)0.0197 (16)0.0126 (15)
N40.080 (2)0.0517 (18)0.0458 (19)0.0110 (16)0.0107 (16)0.0067 (15)
C10.128 (5)0.140 (5)0.147 (5)0.012 (4)0.013 (4)0.021 (4)
C20.122 (4)0.081 (3)0.090 (3)0.007 (3)0.037 (3)0.013 (3)
C30.141 (5)0.071 (3)0.062 (3)0.001 (3)0.033 (3)0.010 (2)
C40.119 (4)0.062 (3)0.069 (3)0.010 (2)0.048 (3)0.010 (2)
C50.063 (3)0.050 (2)0.062 (2)0.0004 (18)0.019 (2)0.015 (2)
C60.050 (2)0.041 (2)0.054 (2)0.0016 (16)0.0102 (17)0.0116 (17)
C70.049 (2)0.043 (2)0.061 (2)0.0022 (16)0.0084 (18)0.0152 (18)
C80.048 (2)0.051 (2)0.048 (2)0.0013 (16)0.0046 (17)0.0128 (18)
C90.077 (3)0.059 (2)0.054 (2)0.005 (2)0.010 (2)0.020 (2)
C100.083 (3)0.049 (2)0.065 (3)0.0005 (19)0.009 (2)0.022 (2)
C110.060 (3)0.045 (2)0.057 (2)0.0045 (17)0.0098 (19)0.0112 (18)
C120.071 (3)0.050 (2)0.070 (3)0.006 (2)0.018 (2)0.014 (2)
C130.068 (3)0.063 (3)0.056 (3)0.006 (2)0.003 (2)0.012 (2)
C140.092 (13)0.096 (12)0.078 (12)0.001 (9)0.007 (8)0.025 (8)
C150.106 (14)0.105 (13)0.092 (12)0.010 (9)0.018 (9)0.014 (9)
C14'0.082 (5)0.084 (4)0.050 (4)0.001 (4)0.010 (3)0.011 (3)
C15'0.109 (7)0.097 (5)0.071 (4)0.019 (5)0.036 (5)0.004 (3)
C160.130 (5)0.183 (5)0.121 (4)0.010 (4)0.010 (4)0.074 (4)
C170.102 (4)0.095 (3)0.080 (3)0.009 (3)0.023 (3)0.039 (3)
C180.123 (4)0.067 (3)0.059 (3)0.011 (3)0.029 (3)0.019 (2)
C190.084 (3)0.073 (3)0.066 (3)0.017 (2)0.032 (2)0.019 (2)
C200.057 (3)0.051 (2)0.058 (2)0.0140 (18)0.0106 (19)0.011 (2)
C210.046 (2)0.044 (2)0.049 (2)0.0096 (16)0.0065 (17)0.0060 (17)
C220.055 (2)0.0401 (18)0.051 (2)0.0089 (16)0.0022 (18)0.0044 (17)
C230.048 (2)0.047 (2)0.051 (2)0.0073 (16)0.0044 (17)0.0082 (18)
C240.065 (3)0.051 (2)0.052 (2)0.0103 (18)0.0106 (19)0.0006 (18)
C250.069 (3)0.0368 (19)0.067 (3)0.0105 (17)0.012 (2)0.0035 (19)
C260.050 (2)0.044 (2)0.060 (2)0.0067 (16)0.0114 (18)0.0081 (18)
C270.059 (3)0.046 (2)0.067 (3)0.0092 (18)0.015 (2)0.012 (2)
C280.069 (3)0.067 (3)0.055 (3)0.016 (2)0.010 (2)0.012 (2)
C290.094 (8)0.087 (7)0.067 (6)0.001 (6)0.013 (5)0.002 (5)
C300.132 (9)0.146 (9)0.089 (7)0.002 (7)0.019 (6)0.020 (6)
C29'0.081 (8)0.088 (7)0.050 (6)0.011 (6)0.014 (5)0.017 (5)
C30'0.134 (10)0.097 (7)0.071 (6)0.000 (6)0.028 (6)0.023 (6)
Geometric parameters (Å, º) top
O1—C51.220 (4)C14—C151.535 (10)
O2—C121.214 (4)C14—H14A0.9700
O3—C131.202 (4)C14—H14B0.9700
O4—C131.346 (4)C15—H15A0.9600
O4—C141.453 (9)C15—H15B0.9600
O4—C14'1.479 (5)C15—H15C0.9600
O5—C201.211 (4)C14'—C15'1.497 (7)
O6—C271.220 (4)C14'—H14C0.9700
O7—C281.201 (4)C14'—H14D0.9700
O8—C281.349 (4)C15'—H15D0.9600
O8—C291.459 (7)C15'—H15E0.9600
O8—C29'1.502 (7)C15'—H15F0.9600
N1—C51.386 (4)C16—C171.533 (6)
N1—C121.389 (4)C16—H16A0.9600
N1—C41.467 (5)C16—H16B0.9600
N2—C131.350 (4)C16—H16C0.9600
N2—C81.398 (4)C17—C181.496 (6)
N2—H2C0.8600C17—H17A0.9700
N3—C271.392 (4)C17—H17B0.9700
N3—C201.392 (4)C18—C191.515 (6)
N3—C191.462 (4)C18—H18A0.9700
N4—C281.352 (4)C18—H18B0.9700
N4—C231.402 (4)C19—H19A0.9700
N4—H4C0.8600C19—H19B0.9700
C1—C21.526 (7)C20—C211.488 (5)
C1—H1A0.9600C21—C221.368 (4)
C1—H1B0.9600C21—C261.385 (4)
C1—H1C0.9600C22—C231.403 (4)
C2—C31.485 (6)C22—H22A0.9300
C2—H2A0.9700C23—C241.392 (4)
C2—H2B0.9700C24—C251.388 (5)
C3—C41.515 (6)C24—H24A0.9300
C3—H3A0.9700C25—C261.376 (5)
C3—H3B0.9700C25—H25A0.9300
C4—H4A0.9700C26—C271.473 (5)
C4—H4B0.9700C29—C301.546 (9)
C5—C61.471 (5)C29—H29A0.9700
C6—C71.368 (4)C29—H29B0.9700
C6—C111.391 (4)C30—H30A0.9600
C7—C81.396 (4)C30—H30B0.9600
C7—H7A0.9300C30—H30C0.9600
C8—C91.393 (5)C29'—C30'1.509 (9)
C9—C101.386 (5)C29'—H29C0.9700
C9—H9A0.9300C29'—H29D0.9700
C10—C111.381 (5)C30'—H30D0.9600
C10—H10A0.9300C30'—H30E0.9600
C11—C121.475 (5)C30'—H30F0.9600
C13—O4—C14122.0 (10)O4—C14'—H14D110.5
C13—O4—C14'113.8 (4)C15'—C14'—H14D110.5
C14—O4—C14'22.0 (13)H14C—C14'—H14D108.7
C28—O8—C29120.5 (6)C14'—C15'—H15D109.5
C28—O8—C29'111.8 (5)C14'—C15'—H15E109.5
C29—O8—C29'21.1 (8)H15D—C15'—H15E109.5
C5—N1—C12111.4 (3)C14'—C15'—H15F109.5
C5—N1—C4124.1 (3)H15D—C15'—H15F109.5
C12—N1—C4124.5 (3)H15E—C15'—H15F109.5
C13—N2—C8127.7 (3)C17—C16—H16A109.5
C13—N2—H2C116.2C17—C16—H16B109.5
C8—N2—H2C116.2H16A—C16—H16B109.5
C27—N3—C20111.5 (3)C17—C16—H16C109.5
C27—N3—C19124.6 (3)H16A—C16—H16C109.5
C20—N3—C19123.8 (3)H16B—C16—H16C109.5
C28—N4—C23128.0 (3)C18—C17—C16112.9 (4)
C28—N4—H4C116.0C18—C17—H17A109.0
C23—N4—H4C116.0C16—C17—H17A109.0
C2—C1—H1A109.5C18—C17—H17B109.0
C2—C1—H1B109.5C16—C17—H17B109.0
H1A—C1—H1B109.5H17A—C17—H17B107.8
C2—C1—H1C109.5C17—C18—C19114.5 (4)
H1A—C1—H1C109.5C17—C18—H18A108.6
H1B—C1—H1C109.5C19—C18—H18A108.6
C3—C2—C1113.2 (4)C17—C18—H18B108.6
C3—C2—H2A108.9C19—C18—H18B108.6
C1—C2—H2A108.9H18A—C18—H18B107.6
C3—C2—H2B108.9N3—C19—C18112.2 (3)
C1—C2—H2B108.9N3—C19—H19A109.2
H2A—C2—H2B107.8C18—C19—H19A109.2
C2—C3—C4114.4 (4)N3—C19—H19B109.2
C2—C3—H3A108.7C18—C19—H19B109.2
C4—C3—H3A108.7H19A—C19—H19B107.9
C2—C3—H3B108.7O5—C20—N3125.1 (3)
C4—C3—H3B108.7O5—C20—C21129.1 (3)
H3A—C3—H3B107.6N3—C20—C21105.8 (3)
N1—C4—C3112.8 (3)C22—C21—C26122.3 (3)
N1—C4—H4A109.0C22—C21—C20129.6 (3)
C3—C4—H4A109.0C26—C21—C20108.1 (3)
N1—C4—H4B109.0C21—C22—C23117.7 (3)
C3—C4—H4B109.0C21—C22—H22A121.1
H4A—C4—H4B107.8C23—C22—H22A121.1
O1—C5—N1124.4 (3)C24—C23—N4123.6 (3)
O1—C5—C6129.1 (3)C24—C23—C22120.2 (3)
N1—C5—C6106.5 (3)N4—C23—C22116.2 (3)
C7—C6—C11121.9 (3)C25—C24—C23120.9 (3)
C7—C6—C5130.1 (3)C25—C24—H24A119.6
C11—C6—C5108.0 (3)C23—C24—H24A119.6
C6—C7—C8118.2 (3)C26—C25—C24118.7 (3)
C6—C7—H7A120.9C26—C25—H25A120.7
C8—C7—H7A120.9C24—C25—H25A120.7
C9—C8—C7120.3 (3)C25—C26—C21120.2 (3)
C9—C8—N2123.4 (3)C25—C26—C27131.8 (3)
C7—C8—N2116.4 (3)C21—C26—C27107.9 (3)
C10—C9—C8120.8 (3)O6—C27—N3124.3 (3)
C10—C9—H9A119.6O6—C27—C26129.1 (3)
C8—C9—H9A119.6N3—C27—C26106.6 (3)
C11—C10—C9118.7 (3)O7—C28—O8123.7 (3)
C11—C10—H10A120.7O7—C28—N4127.7 (3)
C9—C10—H10A120.7O8—C28—N4108.5 (3)
C10—C11—C6120.1 (3)O8—C29—C30100.2 (8)
C10—C11—C12132.3 (3)O8—C29—H29A111.7
C6—C11—C12107.6 (3)C30—C29—H29A111.7
O2—C12—N1124.6 (4)O8—C29—H29B111.7
O2—C12—C11128.9 (4)C30—C29—H29B111.7
N1—C12—C11106.5 (3)H29A—C29—H29B109.5
O3—C13—O4123.5 (3)C29—C30—H30A109.5
O3—C13—N2127.5 (4)C29—C30—H30B109.5
O4—C13—N2109.1 (3)H30A—C30—H30B109.5
O4—C14—C15105 (2)C29—C30—H30C109.5
O4—C14—H14A110.7H30A—C30—H30C109.5
C15—C14—H14A110.7H30B—C30—H30C109.5
O4—C14—H14B110.7O8—C29'—C30'106.4 (8)
C15—C14—H14B110.7O8—C29'—H29C110.4
H14A—C14—H14B108.8C30'—C29'—H29C110.4
C14—C15—H15A109.5O8—C29'—H29D110.4
C14—C15—H15B109.5C30'—C29'—H29D110.4
H15A—C15—H15B109.5H29C—C29'—H29D108.6
C14—C15—H15C109.5C29'—C30'—H30D109.5
H15A—C15—H15C109.5C29'—C30'—H30E109.5
H15B—C15—H15C109.5H30D—C30'—H30E109.5
O4—C14'—C15'106.0 (6)C29'—C30'—H30F109.5
O4—C14'—H14C110.5H30D—C30'—H30F109.5
C15'—C14'—H14C110.5H30E—C30'—H30F109.5
C1—C2—C3—C4175.8 (4)C16—C17—C18—C19179.4 (4)
C5—N1—C4—C379.9 (5)C27—N3—C19—C18104.9 (4)
C12—N1—C4—C399.6 (4)C20—N3—C19—C1876.9 (4)
C2—C3—C4—N162.6 (5)C17—C18—C19—N365.3 (4)
C12—N1—C5—O1179.2 (4)C27—N3—C20—O5179.8 (3)
C4—N1—C5—O11.2 (6)C19—N3—C20—O51.7 (6)
C12—N1—C5—C60.0 (4)C27—N3—C20—C211.0 (4)
C4—N1—C5—C6179.5 (3)C19—N3—C20—C21177.4 (3)
O1—C5—C6—C70.8 (7)O5—C20—C21—C222.2 (6)
N1—C5—C6—C7180.0 (3)N3—C20—C21—C22176.9 (3)
O1—C5—C6—C11179.2 (4)O5—C20—C21—C26179.5 (4)
N1—C5—C6—C110.1 (4)N3—C20—C21—C261.4 (4)
C11—C6—C7—C80.2 (5)C26—C21—C22—C230.0 (5)
C5—C6—C7—C8179.7 (3)C20—C21—C22—C23178.1 (3)
C6—C7—C8—C90.3 (5)C28—N4—C23—C241.3 (6)
C6—C7—C8—N2179.4 (3)C28—N4—C23—C22178.5 (3)
C13—N2—C8—C92.8 (6)C21—C22—C23—C240.5 (5)
C13—N2—C8—C7177.6 (3)C21—C22—C23—N4179.3 (3)
C7—C8—C9—C100.6 (5)N4—C23—C24—C25179.1 (3)
N2—C8—C9—C10179.0 (3)C22—C23—C24—C250.8 (5)
C8—C9—C10—C110.3 (6)C23—C24—C25—C260.5 (5)
C9—C10—C11—C60.1 (6)C24—C25—C26—C210.0 (5)
C9—C10—C11—C12179.6 (4)C24—C25—C26—C27176.8 (4)
C7—C6—C11—C100.4 (5)C22—C21—C26—C250.2 (5)
C5—C6—C11—C10179.5 (3)C20—C21—C26—C25178.7 (3)
C7—C6—C11—C12180.0 (3)C22—C21—C26—C27177.2 (3)
C5—C6—C11—C120.0 (4)C20—C21—C26—C271.3 (4)
C5—N1—C12—O2179.6 (4)C20—N3—C27—O6179.6 (3)
C4—N1—C12—O20.8 (6)C19—N3—C27—O61.9 (6)
C5—N1—C12—C110.0 (4)C20—N3—C27—C260.3 (4)
C4—N1—C12—C11179.6 (4)C19—N3—C27—C26178.1 (3)
C10—C11—C12—O20.2 (7)C25—C26—C27—O62.4 (7)
C6—C11—C12—O2179.6 (4)C21—C26—C27—O6179.5 (4)
C10—C11—C12—N1179.4 (4)C25—C26—C27—N3177.7 (4)
C6—C11—C12—N10.0 (4)C21—C26—C27—N30.6 (4)
C14—O4—C13—O316.0 (17)C29—O8—C28—O711.5 (8)
C14'—O4—C13—O37.1 (7)C29'—O8—C28—O710.0 (10)
C14—O4—C13—N2164.8 (16)C29—O8—C28—N4168.1 (7)
C14'—O4—C13—N2172.1 (6)C29'—O8—C28—N4170.5 (9)
C8—N2—C13—O33.6 (7)C23—N4—C28—O71.0 (7)
C8—N2—C13—O4177.3 (3)C23—N4—C28—O8179.5 (3)
C13—O4—C14—C15138 (2)C28—O8—C29—C30118.3 (12)
C14'—O4—C14—C1564 (3)C29'—O8—C29—C3047.6 (18)
C13—O4—C14'—C15'174.6 (9)C28—O8—C29'—C30'174.7 (14)
C14—O4—C14'—C15'57 (3)C29—O8—C29'—C30'66 (2)

Experimental details

Crystal data
Chemical formulaC15H18N2O4
Mr290.31
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)6.933 (2), 14.210 (4), 15.913 (5)
α, β, γ (°)99.657 (6), 101.373 (6), 91.120 (6)
V3)1512.8 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.20 × 0.08
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.808, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
7713, 5277, 2549
Rint0.035
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.168, 1.03
No. of reflections5277
No. of parameters418
No. of restraints144
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.31

Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Selected geometric parameters (Å, º) top
O1—C51.220 (4)N1—C51.386 (4)
O4—C131.346 (4)N2—C131.350 (4)
O5—C201.211 (4)N3—C271.392 (4)
O8—C281.349 (4)N4—C281.352 (4)
C13—O4—C14122.0 (10)C27—N3—C20111.5 (3)
C28—O8—C29120.5 (6)C28—N4—C23128.0 (3)
C5—N1—C12111.4 (3)O1—C5—C6129.1 (3)
C13—N2—C8127.7 (3)O5—C20—C21129.1 (3)
 

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