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The aci­nitro group in the title compound, C6H16N+·C17H17N2O5-, is almost coplanar with the isoxazoline ring, which assumes a flattened envelope conformation. The cyclo­hexanone ring adopts a half-chair conformation and carries a perpendicular [83.54 (10)°] phenyl ring and a bent [64.30 (17)°] acetyl group. The triethyl­ammonium residue forms a hydrogen bond with the nitro­nate moiety. Intermolecular interaction is exerted through a hydrogen bond between the acidic H atom of the cyclo­hexanone ring and the N atom of the isoxazoline ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016598/cm6016sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016598/cm6016Isup2.hkl
Contains datablock I

CCDC reference: 198966

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.125
  • Data-to-parameter ratio = 10.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 30.00 From the CIF: _reflns_number_total 3539 Count of symmetry unique reflns 3546 Completeness (_total/calc) 99.80% 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 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.

Comment top

Spiroisoxazolines display a range of biological activity, including herbicidal, plant hormones and anticancer properties (Howe & Shelton, 1990; De Amici et al., 1990; Smietana et al., 1999). The title compound, (I), was obtained from a high stereoselective reaction in which three chiral centres are introduced in one step (Adamo et al., 2002). The interest in the relative configuration of the chiral centres and the structural details of this novel 3-acinitroisoxazoline prompted us to undertake a detailed analysis of the structure of compound (I).

The nitronate moiety is almost coplanar [4.62 (9)°] with the isoxazoline ring. The conjugation shows only a small effect both on the C=N bond length in the nitronate [N2—C14 = 1.321 (3) Å] and on the C=N and N—O bonds in the isoxazoline ring [N1—C13 = 1.289 (3) and N1—O2 = 1.425 (2) Å]. In comparison, the length of a C=N bond in a non-conjugated 2-nitropropanate has been reported as 1.311 (7) Å (Reetz et al., 1995) and the length of a C=N and an N—O bond in a non-conjugated nitroisaxazoline as 1.272 (4) and 1.419 (3) Å, respectively (Donati et al., 1994). These data exclude significative push-pull effects.

The isoxazoline ring assumes a very flattened envelope conformation, with puckering parameters (Cremer & Pople, 1975) ϕ = −173 (2)° and Q= 0.062 (2) Å and asymmetry parameter (Nardelli 1983) Δs (C4) 0.006 (1). The cyclohexanone ring lies perpendicular [85.84 (7)°] to the isoxazoline ring and assumes a chair conformation, with puckering parameters θ =172.6 (2)° and QT =-0.533 (2) Å. The phenyl group is approximatively perpendicular [83.54 (10)°] to the least-squares plane through the cyclohexanone, while the acetyl group forms an angle of 64.30 (17)° with this plane.

The nitrogen atom N3 of the triethylammonium residue is linked via a hydrogen bond with the oxygen atom O4 of the acinitro group and it is not coplanar with this group [dihedral angle C14—N2—O4—N3 = 148.1 (2)°]. There is also an intermolecular hydrogen bond between H1 in the cyclohexanone ring and N1 of the isoxazoline ring. Other short contact interactions are reported in Table 2.

Experimental top

A solution of 3-methyl-4-nitro-5-styrylisoxazole (1.15 g, 5.6 mmoles) and acetylacetone (1.5 g, 15 mmoles) in triethylamine (20 ml) and tetrahydrofuran (20 ml) was stirred at 353 K. After 3 h the reaction mixture was allowed to cool at room temperature and the solid obtained was filtered and washed with cold acetone (m.p. 428 K, from ethanol).

Refinement top

3488 Friedel pairs were merged before refinement. The absolute configuration was not determined.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. View of (I), with the atomic numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
Triethylammonium 8-Acetyl-3-methyl-9-phenyl-7-oxo-2-azaspiro [4.5]dec-2-en-4-nitronate top
Crystal data top
C17H17N2O5·C6H16NF(000) = 928
Mr = 431.52Dx = 1.180 Mg m3
Monoclinic, CcMelting point: 428 K
Hall symbol: C -2ycMo Kα radiation, λ = 0.71073 Å
a = 21.815 (3) ÅCell parameters from 44 reflections
b = 10.464 (2) Åθ = 3–25°
c = 11.222 (2) ŵ = 0.08 mm1
β = 108.55 (1)°T = 293 K
V = 2428.6 (7) Å3Needles, colourless
Z = 40.4 × 0.4 × 0.2 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.017
Radiation source: sealed tubeθmax = 30.0°, θmin = 2.7°
Graphite monochromatorh = 3030
ω scansk = 1414
7207 measured reflectionsl = 1515
3539 independent reflections3 standard reflections every 97 reflections
2723 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0828P)2]
where P = (Fo2 + 2Fc2)/3
3539 reflections(Δ/σ)max = 0.014
345 parametersΔρmax = 0.21 e Å3
2 restraintsΔρmin = 0.13 e Å3
Crystal data top
C17H17N2O5·C6H16NV = 2428.6 (7) Å3
Mr = 431.52Z = 4
Monoclinic, CcMo Kα radiation
a = 21.815 (3) ŵ = 0.08 mm1
b = 10.464 (2) ÅT = 293 K
c = 11.222 (2) Å0.4 × 0.4 × 0.2 mm
β = 108.55 (1)°
Data collection top
Siemens P4
diffractometer
Rint = 0.017
7207 measured reflections3 standard reflections every 97 reflections
3539 independent reflections intensity decay: none
2723 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0432 restraints
wR(F2) = 0.125H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.21 e Å3
3539 reflectionsΔρmin = 0.13 e Å3
345 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 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
O10.17473 (10)0.60683 (19)0.0287 (2)0.0633 (7)
O20.06787 (8)0.61062 (16)0.22264 (15)0.0446 (5)
O30.14099 (9)0.6493 (2)0.02743 (19)0.0600 (6)
O40.08001 (10)0.5440 (2)0.11724 (17)0.0592 (6)
O50.23920 (11)0.3558 (3)0.1935 (2)0.0819 (9)
N10.02610 (11)0.67852 (18)0.27551 (18)0.0444 (6)
N20.08550 (9)0.6024 (2)0.01949 (18)0.0449 (6)
C10.13438 (10)0.39925 (19)0.05260 (19)0.0346 (5)
C20.10193 (10)0.35869 (19)0.15068 (18)0.0335 (5)
C30.03275 (10)0.4114 (2)0.1140 (2)0.0354 (5)
C40.03063 (10)0.55664 (19)0.10056 (18)0.0347 (5)
C50.06273 (12)0.5991 (2)0.0047 (2)0.0418 (6)
C60.12882 (11)0.5427 (2)0.02993 (19)0.0380 (6)
C70.10082 (11)0.2143 (2)0.1660 (2)0.0375 (6)
C80.12618 (15)0.1601 (3)0.2841 (3)0.0533 (9)
C90.1228 (2)0.0290 (3)0.2999 (3)0.0731 (13)
C100.0947 (2)0.0491 (3)0.1990 (4)0.0757 (15)
C110.0697 (2)0.0033 (3)0.0812 (4)0.0733 (10)
C120.07268 (16)0.1348 (2)0.0641 (3)0.0542 (8)
C130.03143 (12)0.6807 (2)0.1958 (2)0.0417 (6)
C140.03481 (10)0.6136 (2)0.0827 (2)0.0379 (6)
C150.08378 (17)0.7484 (4)0.2288 (3)0.0691 (11)
C160.20518 (12)0.3611 (3)0.0869 (3)0.0508 (8)
C170.22978 (19)0.3340 (5)0.0204 (4)0.0855 (14)
N30.32714 (12)0.1884 (3)0.6970 (2)0.0558 (7)
C180.3275 (3)0.3253 (4)0.7341 (4)0.0860 (16)
C190.35420 (18)0.1660 (4)0.5920 (4)0.0802 (15)
C200.26075 (15)0.1334 (3)0.6720 (3)0.0653 (10)
C210.2580 (2)0.0078 (4)0.6512 (4)0.0870 (14)
C220.3179 (3)0.2315 (9)0.4724 (4)0.136 (3)
C230.3939 (4)0.3808 (5)0.7842 (7)0.146 (3)
H10.1126 (14)0.364 (3)0.029 (3)0.0415*
H20.1279 (14)0.391 (3)0.235 (3)0.0402*
H3A0.0069 (15)0.372 (3)0.037 (3)0.047 (7)*
H3B0.0121 (16)0.390 (3)0.178 (3)0.059 (9)*
H5A0.0377 (14)0.565 (2)0.076 (3)0.039 (6)*
H5B0.0620 (14)0.686 (3)0.003 (3)0.049 (8)*
H80.1486 (16)0.212 (3)0.353 (3)0.056 (8)*
H90.1381 (18)0.009 (4)0.389 (4)0.071 (10)*
H100.095 (2)0.136 (4)0.209 (4)0.073 (10)*
H110.051 (2)0.043 (4)0.006 (4)0.087 (12)*
H120.0597 (15)0.170 (3)0.017 (3)0.048 (8)*
H15A0.067720.777050.314370.0828*
H15B0.119450.691210.219000.0828*
H15C0.097950.820650.174190.0828*
H17A0.276100.328220.010010.1026*
H17B0.217020.401740.080940.1026*
H17C0.212040.254650.059160.1026*
H18A0.306270.333030.797650.15 (2)*
H18B0.302750.374580.661500.084 (13)*
H19A0.398720.195110.618160.091 (13)*
H19B0.354340.074840.576460.093 (13)*
H20A0.245840.152410.742820.093 (13)*
H20B0.231450.174590.598410.083 (12)*
H21A0.216000.038950.646960.166 (9)*
H21B0.290240.048680.719550.166 (9)*
H21C0.266130.026500.573820.166 (9)*
H22A0.339080.216100.410640.166 (9)*
H22B0.316790.321760.486980.166 (9)*
H22C0.274580.198920.442380.166 (9)*
H23A0.391390.465310.815660.166 (9)*
H23B0.413040.384920.718130.166 (9)*
H23C0.420070.327930.851020.166 (9)*
H320.353 (2)0.146 (4)0.763 (4)0.082 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0482 (10)0.0493 (10)0.0930 (15)0.0093 (8)0.0232 (10)0.0147 (10)
O20.0382 (8)0.0472 (9)0.0393 (8)0.0048 (7)0.0007 (6)0.0100 (7)
O30.0366 (9)0.0781 (13)0.0583 (10)0.0178 (9)0.0052 (8)0.0044 (9)
O40.0503 (10)0.0753 (13)0.0405 (8)0.0111 (9)0.0016 (7)0.0148 (8)
O50.0411 (10)0.126 (2)0.0686 (14)0.0160 (12)0.0034 (10)0.0247 (14)
N10.0536 (11)0.0428 (9)0.0348 (9)0.0023 (9)0.0113 (8)0.0063 (8)
N20.0375 (10)0.0502 (11)0.0412 (10)0.0072 (8)0.0042 (8)0.0032 (8)
C10.0325 (9)0.0350 (10)0.0346 (9)0.0014 (8)0.0083 (8)0.0012 (8)
C20.0361 (9)0.0306 (9)0.0315 (9)0.0012 (7)0.0075 (7)0.0019 (7)
C30.0337 (9)0.0338 (9)0.0377 (10)0.0008 (8)0.0101 (8)0.0014 (8)
C40.0344 (9)0.0336 (9)0.0317 (9)0.0030 (8)0.0041 (7)0.0018 (8)
C50.0453 (12)0.0357 (10)0.0432 (11)0.0055 (9)0.0125 (9)0.0091 (9)
C60.0387 (10)0.0381 (10)0.0356 (10)0.0018 (8)0.0095 (8)0.0045 (8)
C70.0394 (10)0.0316 (9)0.0423 (10)0.0011 (8)0.0140 (8)0.0046 (8)
C80.0706 (18)0.0446 (13)0.0443 (13)0.0067 (12)0.0176 (12)0.0085 (11)
C90.106 (3)0.0512 (16)0.0673 (19)0.0092 (16)0.0350 (18)0.0250 (14)
C100.100 (3)0.0364 (14)0.095 (3)0.0044 (16)0.037 (2)0.0147 (16)
C110.087 (2)0.0393 (13)0.085 (2)0.0135 (15)0.0153 (18)0.0085 (15)
C120.0666 (16)0.0372 (11)0.0498 (13)0.0050 (12)0.0059 (12)0.0002 (11)
C130.0481 (12)0.0379 (10)0.0400 (11)0.0036 (9)0.0152 (9)0.0012 (8)
C140.0349 (10)0.0389 (10)0.0367 (10)0.0043 (8)0.0070 (8)0.0004 (8)
C150.0641 (17)0.077 (2)0.0710 (18)0.0127 (15)0.0283 (15)0.0187 (16)
C160.0388 (12)0.0519 (13)0.0625 (15)0.0084 (10)0.0173 (11)0.0116 (11)
C170.069 (2)0.110 (3)0.090 (2)0.035 (2)0.043 (2)0.011 (2)
N30.0531 (12)0.0605 (13)0.0446 (11)0.0079 (10)0.0024 (9)0.0052 (10)
C180.124 (4)0.0615 (19)0.073 (2)0.004 (2)0.032 (2)0.0031 (17)
C190.0588 (18)0.095 (3)0.093 (3)0.0086 (17)0.0328 (19)0.010 (2)
C200.0542 (16)0.079 (2)0.0634 (18)0.0094 (15)0.0199 (14)0.0016 (15)
C210.070 (2)0.078 (2)0.106 (3)0.0058 (19)0.018 (2)0.004 (2)
C220.125 (4)0.231 (8)0.065 (2)0.002 (5)0.049 (3)0.014 (4)
C230.171 (6)0.084 (3)0.142 (5)0.051 (4)0.009 (5)0.009 (3)
Geometric parameters (Å, º) top
O1—C61.209 (3)C3—H3B0.99 (3)
O2—N11.425 (3)C5—H5A0.96 (3)
O2—C41.466 (3)C5—H5B0.91 (3)
O3—N21.283 (3)C8—H80.94 (3)
O4—N21.294 (3)C9—H91.03 (4)
O5—C161.192 (4)C10—H100.92 (4)
N1—C131.289 (3)C11—H110.95 (4)
N2—C141.321 (3)C12—H120.94 (3)
N3—C201.500 (4)C15—H15A0.9595
N3—C181.491 (5)C15—H15C0.9603
N3—C191.495 (5)C15—H15B0.9598
N3—H320.89 (4)C17—H17A0.9601
C1—C61.521 (3)C17—H17B0.9598
C1—C161.521 (4)C17—H17C0.9598
C1—C21.545 (3)C18—C231.494 (10)
C2—C31.535 (3)C19—C221.491 (7)
C2—C71.522 (3)C20—C211.494 (5)
C3—C41.527 (3)C18—H18A0.9694
C4—C51.525 (3)C18—H18B0.9702
C4—C141.500 (3)C19—H19A0.9699
C5—C61.499 (4)C19—H19B0.9699
C7—C81.385 (4)C20—H20A0.9703
C7—C121.389 (4)C20—H20B0.9698
C8—C91.388 (4)C21—H21A0.9593
C9—C101.373 (5)C21—H21B0.9606
C10—C111.374 (6)C21—H21C0.9601
C11—C121.394 (4)C22—H22A0.9610
C13—C151.487 (5)C22—H22B0.9602
C13—C141.432 (3)C22—H22C0.9593
C16—C171.493 (5)C23—H23A0.9602
C1—H10.96 (3)C23—H23B0.9607
C2—H20.99 (3)C23—H23C0.9602
C3—H3A0.96 (3)
O1···C173.212 (5)H1···O2i2.66 (3)
O1···C20i3.402 (4)H1···H17B2.5553
O3···C20ii3.376 (4)H1···N1i2.44 (3)
O3···C18ii3.139 (5)H2···O22.63 (3)
O3···N3ii2.974 (3)H2···O52.64 (3)
O3···C152.936 (4)H2···H82.26 (4)
O4···C19ii3.370 (5)H3A···O42.78 (3)
O4···C33.263 (3)H3A···C122.83 (3)
O4···C53.032 (3)H3A···H5A2.58 (4)
O4···N3ii2.836 (3)H3A···H122.57 (5)
O5···C223.319 (6)H3B···H19Av2.5110
O5···C73.288 (4)H5A···O42.47 (3)
O1···H17B2.7736H5A···H3A2.58 (4)
O1···H8i2.66 (3)H8···H22.26 (4)
O1···H18Bi2.7222H8···O1iv2.66 (3)
O1···H20Bi2.5997H9···C11x2.99 (4)
O2···H10iii2.73 (4)H9···C12x3.07 (4)
O2···H1iv2.66 (3)H10···N1xi2.70 (4)
O2···H22.63 (3)H10···O2xi2.73 (4)
O3···H23Cii2.8783H12···C33.07 (3)
O3···H21Cv2.9176H12···H12.36 (5)
O3···H32ii2.31 (4)H12···H3A2.57 (5)
O3···H18Aii2.7269H12···N1i2.72 (3)
O3···H15C2.8043H12···C12.87 (3)
O3···H19Bv2.6355H15B···O32.6896
O3···H17Avi2.7270H15B···H22Avi2.5979
O3···H15B2.6896H15B···H21Bv2.4725
O4···H5A2.47 (3)H15C···O32.8043
O4···H32ii1.96 (4)H17A···O3xii2.7270
O4···H3A2.78 (3)H17B···O12.7736
O5···H22.64 (3)H17B···H12.5553
N1···C1iv3.352 (3)H17B···C62.9915
N2···N3ii3.272 (3)H17C···H12.5684
N3···O4vii2.836 (3)H18A···C17xiii3.0202
N3···N2vii3.272 (3)H18A···H20A2.2743
N3···O3vii2.974 (3)H18A···O3vii2.7269
N1···H1iv2.44 (3)H18B···C222.7019
N1···H12iv2.72 (3)H18B···H20B2.5689
N1···H10iii2.70 (4)H18B···H22B2.1486
N2···H23Cii2.7943H18B···O1iv2.7222
N2···H32ii2.43 (4)H19A···C232.7172
N2···H19Bv2.6871H19A···H23B2.2535
C1···N1i3.352 (3)H19A···H3Bxiv2.5110
C3···O43.263 (3)H19B···C212.6438
C5···O43.032 (3)H19B···H21C2.1891
C7···O53.288 (4)H19B···O3xiv2.6355
C15···O32.936 (4)H19B···N2xiv2.6871
C17···O13.212 (5)H20A···H18A2.2743
C18···O3vii3.139 (5)H20B···C222.7582
C19···O4vii3.370 (5)H20B···H18B2.5689
C20···O1iv3.402 (4)H20B···H22C2.2504
C20···O3vii3.376 (4)H20B···O1iv2.5997
C22···O53.319 (6)H21A···C9x3.0513
C1···H122.87 (3)H21A···C10x3.0291
C3···H123.07 (3)H21A···C11x3.0612
C6···H17B2.9915H21B···H322.4161
C9···H21Aviii3.0513H21B···H15Bxiv2.4725
C10···H21Aviii3.0291H21C···C192.7461
C11···H21Aviii3.0612H21C···H19B2.1891
C11···H9viii2.99 (4)H21C···O3xiv2.9176
C12···H12.86 (3)H22A···C15xii3.0488
C12···H9viii3.07 (4)H22A···H15Bxii2.5979
C12···H3A2.83 (3)H22B···C182.7082
C15···H22Avi3.0488H22B···H18B2.1486
C17···H18Aix3.0202H22C···C202.7741
C18···H22B2.7082H22C···H20B2.2504
C19···H23B2.7826H23B···C192.7826
C19···H21C2.7461H23B···H19A2.2535
C20···H22C2.7741H23C···H322.4127
C21···H19B2.6438H23C···O3vii2.8783
C22···H18B2.7019H23C···N2vii2.7943
C22···H20B2.7582H32···H21B2.4161
C23···H19A2.7172H32···H23C2.4127
H1···C122.86 (3)H32···O3vii2.31 (4)
H1···H122.36 (5)H32···O4vii1.96 (4)
H1···H17C2.5684H32···N2vii2.43 (4)
N1—O2—C4110.10 (17)C6—C5—H5B113 (2)
O2—N1—C13109.28 (18)C7—C8—H8119.6 (19)
O3—N2—O4117.5 (2)C9—C8—H8119.9 (19)
O3—N2—C14122.5 (2)C10—C9—H9120 (2)
O4—N2—C14120.0 (2)C8—C9—H9120 (2)
C18—N3—C20109.9 (3)C9—C10—H10120 (3)
C19—N3—C20113.1 (3)C11—C10—H10120 (3)
C18—N3—C19113.7 (3)C10—C11—H11126 (3)
C18—N3—H32107 (3)C12—C11—H11114 (3)
C19—N3—H32106 (3)C11—C12—H12120.5 (19)
C20—N3—H32106 (3)C7—C12—H12118.8 (19)
C2—C1—C6111.10 (17)C13—C15—H15B109.46
C6—C1—C16108.8 (2)C13—C15—H15C109.44
C2—C1—C16113.95 (19)C13—C15—H15A109.46
C3—C2—C7109.72 (18)H15A—C15—H15B109.52
C1—C2—C7112.36 (17)H15B—C15—H15C109.46
C1—C2—C3110.14 (16)H15A—C15—H15C109.49
C2—C3—C4112.37 (18)C16—C17—H17C109.46
C5—C4—C14114.90 (18)H17A—C17—H17B109.49
O2—C4—C3107.52 (16)C16—C17—H17B109.44
O2—C4—C5107.75 (17)H17B—C17—H17C109.50
C3—C4—C14113.97 (18)H17A—C17—H17C109.49
C3—C4—C5110.71 (17)C16—C17—H17A109.45
O2—C4—C14101.11 (16)N3—C18—C23113.4 (5)
C4—C5—C6112.46 (18)N3—C19—C22114.1 (4)
C1—C6—C5116.16 (19)N3—C20—C21113.4 (3)
O1—C6—C1121.8 (2)N3—C18—H18A108.92
O1—C6—C5122.0 (2)N3—C18—H18B108.91
C8—C7—C12118.7 (2)C23—C18—H18A108.88
C2—C7—C8119.9 (2)C23—C18—H18B108.86
C2—C7—C12121.35 (19)H18A—C18—H18B107.75
C7—C8—C9120.4 (3)N3—C19—H19A108.70
C8—C9—C10120.7 (3)N3—C19—H19B108.70
C9—C10—C11119.5 (3)C22—C19—H19A108.79
C10—C11—C12120.3 (3)C22—C19—H19B108.75
C7—C12—C11120.4 (3)H19A—C19—H19B107.65
N1—C13—C14111.8 (2)N3—C20—H20A108.88
C14—C13—C15128.8 (2)N3—C20—H20B108.93
N1—C13—C15119.4 (2)C21—C20—H20A108.87
C4—C14—C13107.33 (19)C21—C20—H20B108.88
N2—C14—C4125.37 (19)H20A—C20—H20B107.73
N2—C14—C13127.3 (2)C20—C21—H21A109.51
O5—C16—C1121.6 (3)C20—C21—H21B109.44
O5—C16—C17122.1 (3)C20—C21—H21C109.45
C1—C16—C17116.2 (3)H21A—C21—H21B109.48
C16—C1—H1107.1 (19)H21A—C21—H21C109.53
C6—C1—H1103.3 (19)H21B—C21—H21C109.42
C2—C1—H1111.9 (19)C19—C22—H22A109.43
C3—C2—H2110.3 (18)C19—C22—H22B109.50
C7—C2—H2104.8 (18)C19—C22—H22C109.55
C1—C2—H2109.4 (18)H22A—C22—H22B109.38
H3A—C3—H3B106 (3)H22A—C22—H22C109.46
C2—C3—H3A109 (2)H22B—C22—H22C109.51
C4—C3—H3B106.9 (19)C18—C23—H23A109.54
C2—C3—H3B111 (2)C18—C23—H23B109.53
C4—C3—H3A110.3 (19)C18—C23—H23C109.53
C4—C5—H5B111 (2)H23A—C23—H23B109.39
C4—C5—H5A107.7 (18)H23A—C23—H23C109.44
C6—C5—H5A104.8 (18)H23B—C23—H23C109.40
H5A—C5—H5B107 (2)
C4—O2—N1—C134.9 (2)C3—C2—C7—C1266.5 (3)
N1—O2—C4—C3113.36 (19)C1—C2—C7—C8125.9 (3)
N1—O2—C4—C5127.28 (18)C1—C2—C3—C457.3 (2)
N1—O2—C4—C146.4 (2)C7—C2—C3—C4178.46 (17)
O2—N1—C13—C140.9 (3)C2—C3—C4—O260.7 (2)
O2—N1—C13—C15179.0 (2)C2—C3—C4—C556.8 (2)
O3—N2—C14—C4177.3 (2)C2—C3—C4—C14171.85 (17)
O3—N2—C14—C132.6 (4)C14—C4—C5—C6178.02 (17)
O4—N2—C14—C43.8 (3)C3—C4—C14—N270.6 (3)
O4—N2—C14—C13176.3 (2)O2—C4—C14—N2174.3 (2)
C20—N3—C19—C2264.9 (5)O2—C4—C14—C135.7 (2)
C18—N3—C20—C21172.2 (3)O2—C4—C5—C666.2 (2)
C19—N3—C20—C2159.6 (4)C3—C4—C5—C651.1 (2)
C20—N3—C18—C23169.0 (4)C5—C4—C14—C13121.4 (2)
C18—N3—C19—C2261.4 (5)C3—C4—C14—C13109.3 (2)
C19—N3—C18—C2363.1 (5)C5—C4—C14—N258.6 (3)
C6—C1—C16—C1786.0 (3)C4—C5—C6—O1133.1 (2)
C16—C1—C6—O16.7 (3)C4—C5—C6—C149.0 (2)
C16—C1—C6—C5175.4 (2)C2—C7—C8—C9177.1 (3)
C2—C1—C16—O532.0 (4)C12—C7—C8—C90.7 (5)
C2—C1—C16—C17149.5 (3)C2—C7—C12—C11177.2 (3)
C6—C1—C16—O592.6 (3)C8—C7—C12—C110.5 (5)
C6—C1—C2—C351.7 (2)C7—C8—C9—C100.4 (6)
C6—C1—C2—C7174.36 (18)C8—C9—C10—C110.0 (7)
C16—C1—C2—C3174.99 (19)C9—C10—C11—C120.1 (7)
C16—C1—C2—C762.4 (2)C10—C11—C12—C70.1 (6)
C2—C1—C6—O1132.9 (2)N1—C13—C14—C43.3 (3)
C2—C1—C6—C549.2 (2)C15—C13—C14—N23.1 (4)
C1—C2—C7—C1256.4 (3)N1—C13—C14—N2176.8 (2)
C3—C2—C7—C8111.2 (3)C15—C13—C14—C4176.8 (3)
Symmetry codes: (i) x, y+1, z1/2; (ii) x1/2, y+1/2, z1; (iii) x, y+1, z; (iv) x, y+1, z+1/2; (v) x1/2, y+1/2, z1/2; (vi) x1/2, y+1/2, z; (vii) x+1/2, y1/2, z+1; (viii) x, y, z1/2; (ix) x, y, z1; (x) x, y, z+1/2; (xi) x, y1, z; (xii) x+1/2, y1/2, z; (xiii) x, y, z+1; (xiv) x+1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H32···O3vii0.89 (4)2.31 (4)2.974 (3)131 (4)
N3—H32···O4vii0.89 (4)1.96 (4)2.836 (3)168 (4)
N3—H32···N2vii0.89 (4)2.43 (4)3.272 (3)158 (4)
C1—H1···N1i0.96 (3)2.44 (3)3.352 (3)159 (3)
C5—H5A···O40.96 (3)2.47 (3)3.032 (3)117 (2)
C20—H20B···O1iv0.96982.59973.402 (4)140.26
Symmetry codes: (i) x, y+1, z1/2; (iv) x, y+1, z+1/2; (vii) x+1/2, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC17H17N2O5·C6H16N
Mr431.52
Crystal system, space groupMonoclinic, Cc
Temperature (K)293
a, b, c (Å)21.815 (3), 10.464 (2), 11.222 (2)
β (°) 108.55 (1)
V3)2428.6 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.4 × 0.4 × 0.2
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7207, 3539, 2723
Rint0.017
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.125, 1.00
No. of reflections3539
No. of parameters345
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.13

Computer programs: XSCANS (Siemens, 1996), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
O2—N11.425 (3)C3—C41.527 (3)
O2—C41.466 (3)C4—C51.525 (3)
O3—N21.283 (3)C4—C141.500 (3)
O4—N21.294 (3)C13—C151.487 (5)
N1—C131.289 (3)C13—C141.432 (3)
N2—C141.321 (3)
N1—O2—C4110.10 (17)N1—C13—C14111.8 (2)
O2—N1—C13109.28 (18)C14—C13—C15128.8 (2)
O3—N2—O4117.5 (2)N1—C13—C15119.4 (2)
O3—N2—C14122.5 (2)C4—C14—C13107.33 (19)
O4—N2—C14120.0 (2)N2—C14—C4125.37 (19)
O2—C4—C3107.52 (16)N2—C14—C13127.3 (2)
O2—C4—C5107.75 (17)N3—C18—C23113.4 (5)
O2—C4—C14101.11 (16)N3—C19—C22114.1 (4)
O1—C6—C1121.8 (2)N3—C20—C21113.4 (3)
O1—C6—C5122.0 (2)
O4—N2—C14—C43.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H32···O4i0.89 (4)1.96 (4)2.836 (3)168 (4)
C1—H1···N1ii0.96 (3)2.44 (3)3.352 (3)159 (3)
C5—H5A···O40.96 (3)2.47 (3)3.032 (3)117 (2)
C20—H20B···O1iii0.96982.59973.402 (4)140.26
Symmetry codes: (i) x+1/2, y1/2, z+1; (ii) x, y+1, z1/2; (iii) x, y+1, z+1/2.
 

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