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Acta Cryst. (2003). E59, o572-o573
https://doi.org/10.1107/S1600536803004860
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Methyl (\pm)-(1α,2β,8α,9α,10β)-2-chloro-4-aza-3-oxatetra­cyclo­[8.4.0.02,9.04,8]­tetra­decane-9-carboxyl­ate oxalic acid monohydrate

D. S. Yufit, J. A. K. Howard, S. I. Kozhushkov, S. Masini, A. Brandi and A. Meijere
In the crystal structure of the title compound, C14H20ClNO3·C2H2O4·H2O, there are infinitive flat ribbons, parallel to the [0\overline 11] direction. Molecules in the ribbons are linked together by an extensive network of hydrogen bonds.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803004860/cv6174sup1.cif
Contains datablocks global, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803004860/cv6174IVsup2.hkl
Contains datablock IV

CCDC reference: 209991

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.085
  • Data-to-parameter ratio = 14.4

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry


Red Alert Alert Level A:



PLAT_353  Alert A Long    N-H Bond (0.87A)   N1     -   H7O    =       1.34 Ang.


Yellow Alert Alert Level C:



PLAT_369  Alert C Long   C(sp2)-C(sp2) Bond  C15    -   C16    =       1.55 Ang.


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check
Comment top

The tetracyclic title compound, (III), was obtained upon an attempted 1,3-dipolar cycloaddition of 3,4-dihydro-2H-pyrrole 1-oxide, (I), to methyl 2-chloro-2-(bicyclo[4.1.0]hept-7-ylidene)acetate, (II) (Brandi et al., 2003), during systematic studies of 1,3-dipolar cycloadditions to substituted methylenecyclopropanes (Goti et al., 1996; de Meijere, Kozhushkov & Khlebnikov, 2000; de Meijere & Kozhushkov, 2000). The relative configuration of (III) was established by X-ray crystal structure analysis of its solvate with oxalic acid and water (1:1:1) (IV).

Chlorine and methoxycarbonyl substitutents at the two bridgehead atoms of the tetracyclic system are cis-oriented with respect to each other (Fig. 1).

All four cycles are substantially non-planar. The four-membered ring is folded around the C6···C12 line by 14.7(?)°. The cyclohexane ring has a slightly flattened chair conformation, while the five-membered heterocycles adopt conformations of O1-envelope and twisted half-chair. The solvent molecule of oxalic acid is also not entirely plana, with a torsion angle O5—C15—C16—O6 of −7.5(?)°.

The most remarkable feature of the studied structure is the packing of the molecules in the crystal. The molecles of oxalic acid and water form flat ribbons; the tetracyclic molecules are attached to both edges of the ribbons by very strong hydrogen bonds between oxalic acid and the tetradecane N atom (Fig. 2). The molecules of oxalic acid and water are linked together by a network of O—H···O hydrogen bonds. Tetracyclic molecules in the same ribbon are also connected by C6—H6···O3 [C···O = 3.290 (1) Å] interactions. In the crystal structure, these ribbons are parallel to the [011] direction and show a number of weak C—H···O interactions.

Experimental top

Crystals of (III) were obtained by slow evaporation from a solution in Et2O at 277 K.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of all the molecules in (III). Displacement ellipsoids are shown at the 50% probability level and H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Arrangement of the molecules in hydrogen-bonded ribbons.
[Figure 3] Fig. 3. Packing diagram, viewed along a axis.
Methyl (±)-(1α,2β,8α,9α,10β)-2-chloro-3-oxa- 4-azatetracyclo[8.4.02,904,8]tetradecane-9-carboxylate oxalic acid monohydrate top
Crystal data top
C14H20ClNO3·C2H2O4·H2OZ = 2
Mr = 393.81F(000) = 416
Triclinic, P1Dx = 1.428 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6133 (2) ÅCell parameters from 999 reflections
b = 8.0737 (2) Åθ = 10.3–20.8°
c = 17.8848 (5) ŵ = 0.25 mm−1
α = 77.746 (1)°T = 120 K
β = 83.211 (1)°Block, colourless
γ = 80.169 (1)°0.42 × 0.35 × 0.17 mm
V = 916.14 (4) Å3
Data collection top
Bruker SMART-CCD 1K
diffractometer		3835 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 29.0°, θmin = 2.3°
ω scansh = −8→9
11202 measured reflectionsk = −10→10
4763 independent reflectionsl = −24→23
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)] = 0.033Hydrogen site location: difference Fourier map
wR(F2) = 0.085All H-atom parameters refined
S = 1.02 w = 1/[σ2(Fo2) + (0.04P)2 + 0.3P]
where P = (Fo2 + 2Fc2)/3
4763 reflections(Δ/σ)max < 0.001
331 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
C14H20ClNO3·C2H2O4·H2Oγ = 80.169 (1)°
Mr = 393.81V = 916.14 (4) Å3
Triclinic, P1Z = 2
a = 6.6133 (2) ÅMo Kα radiation
b = 8.0737 (2) ŵ = 0.25 mm−1
c = 17.8848 (5) ÅT = 120 K
α = 77.746 (1)°0.42 × 0.35 × 0.17 mm
β = 83.211 (1)°
Data collection top
Bruker SMART-CCD 1K
diffractometer		3835 reflections with I > 2σ(I)
11202 measured reflectionsRint = 0.026
4763 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.085All H-atom parameters refined
S = 1.02Δρmax = 0.39 e Å−3
4763 reflectionsΔρmin = −0.28 e Å−3
331 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*/Ueq
Cl1−0.09069 (5)0.02471 (4)0.163575 (19)0.02746 (9)
O1−0.45991 (14)−0.02751 (11)0.22730 (5)0.02126 (19)
O2−0.06398 (14)−0.55704 (11)0.24933 (5)0.0231 (2)
O30.08735 (14)−0.35793 (12)0.16422 (6)0.0268 (2)
O40.05205 (15)0.17594 (14)0.43769 (7)0.0320 (2)
O5−0.23363 (15)0.34249 (12)0.47483 (6)0.0282 (2)
O6−0.45876 (16)0.16682 (17)0.41118 (9)0.0484 (3)
O7−0.16835 (14)0.03342 (12)0.35997 (5)0.02272 (19)
O1W0.26688 (16)0.31727 (14)0.50902 (6)0.0253 (2)
N1−0.41902 (16)−0.11384 (13)0.30664 (6)0.0183 (2)
C1−0.62385 (19)−0.10868 (17)0.35159 (8)0.0214 (2)
C2−0.71691 (19)−0.25532 (18)0.33415 (8)0.0227 (3)
C3−0.52807 (19)−0.39647 (16)0.33350 (8)0.0204 (2)
C4−0.34408 (18)−0.29981 (15)0.30182 (7)0.0167 (2)
C5−0.26763 (17)−0.29163 (15)0.21625 (7)0.0160 (2)
C6−0.42686 (18)−0.30992 (16)0.15951 (7)0.0176 (2)
C7−0.4024 (2)−0.46438 (17)0.12020 (8)0.0215 (3)
C8−0.2486 (2)−0.45580 (18)0.04882 (8)0.0245 (3)
C9−0.2821 (2)−0.27937 (19)−0.00365 (8)0.0274 (3)
C10−0.2398 (2)−0.14239 (18)0.03772 (8)0.0244 (3)
C11−0.3909 (2)−0.13198 (17)0.10907 (7)0.0212 (2)
C12−0.29973 (19)−0.09861 (16)0.17885 (7)0.0195 (2)
C13−0.05962 (18)−0.40003 (16)0.20571 (7)0.0179 (2)
C140.1218 (2)−0.68069 (18)0.24252 (9)0.0253 (3)
C15−0.14498 (19)0.22915 (16)0.44224 (7)0.0206 (2)
C16−0.2716 (2)0.13487 (17)0.40170 (8)0.0232 (3)
H011−0.593 (2)−0.134 (2)0.4052 (10)0.023 (4)*
H012−0.704 (3)0.003 (2)0.3391 (9)0.026 (4)*
H21−0.773 (2)−0.2169 (19)0.2834 (9)0.021 (4)*
H22−0.825 (3)−0.289 (2)0.3741 (11)0.037 (5)*
H31−0.508 (2)−0.458 (2)0.3860 (10)0.024 (4)*
H32−0.540 (2)−0.483 (2)0.3035 (10)0.026 (4)*
H4−0.231 (2)−0.341 (2)0.3330 (9)0.021 (4)*
H6−0.562 (2)−0.2980 (19)0.1868 (9)0.018 (4)*
H71−0.535 (3)−0.466 (2)0.1042 (10)0.029 (4)*
H72−0.370 (2)−0.572 (2)0.1588 (9)0.023 (4)*
H81−0.108 (2)−0.4761 (19)0.0627 (9)0.020 (4)*
H82−0.264 (2)−0.547 (2)0.0234 (10)0.027 (4)*
H91−0.194 (3)−0.277 (2)−0.0507 (11)0.035 (5)*
H92−0.422 (3)−0.253 (2)−0.0200 (10)0.031 (4)*
H101−0.103 (2)−0.1732 (19)0.0534 (9)0.021 (4)*
H102−0.248 (3)−0.027 (2)0.0034 (11)0.038 (5)*
H11−0.514 (3)−0.054 (2)0.0970 (9)0.026 (4)*
H1410.167 (3)−0.678 (2)0.1889 (11)0.038 (5)*
H1420.223 (3)−0.657 (2)0.2676 (10)0.033 (4)*
H1430.081 (3)−0.793 (2)0.2680 (11)0.037 (5)*
H1W0.243 (3)0.426 (3)0.5090 (12)0.051 (6)*
H2W0.381 (4)0.294 (3)0.4852 (13)0.050 (6)*
H4O0.116 (4)0.236 (3)0.4653 (14)0.069 (7)*
H7O−0.287 (4)−0.037 (3)0.3342 (14)0.071 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.03382 (18)0.02492 (16)0.02669 (17)−0.01474 (13)0.00010 (12)−0.00510 (12)
O10.0257 (5)0.0189 (4)0.0179 (4)0.0015 (3)−0.0037 (3)−0.0036 (3)
O20.0191 (4)0.0190 (4)0.0278 (5)0.0010 (3)0.0028 (3)−0.0026 (4)
O30.0175 (4)0.0281 (5)0.0319 (5)−0.0036 (4)0.0024 (4)−0.0018 (4)
O40.0212 (5)0.0402 (6)0.0435 (6)−0.0067 (4)−0.0001 (4)−0.0278 (5)
O50.0317 (5)0.0255 (5)0.0307 (5)−0.0002 (4)−0.0036 (4)−0.0157 (4)
O60.0203 (5)0.0540 (7)0.0859 (10)−0.0025 (5)0.0006 (5)−0.0524 (7)
O70.0219 (4)0.0241 (5)0.0259 (5)−0.0050 (3)0.0004 (4)−0.0133 (4)
O1W0.0250 (5)0.0259 (5)0.0283 (5)−0.0052 (4)−0.0010 (4)−0.0121 (4)
N10.0203 (5)0.0185 (5)0.0167 (5)−0.0019 (4)−0.0026 (4)−0.0050 (4)
C10.0191 (6)0.0230 (6)0.0219 (6)0.0004 (5)−0.0010 (5)−0.0075 (5)
C20.0173 (6)0.0301 (7)0.0222 (6)−0.0043 (5)−0.0008 (5)−0.0084 (5)
C30.0214 (6)0.0204 (6)0.0201 (6)−0.0056 (5)−0.0002 (5)−0.0048 (5)
C40.0167 (5)0.0163 (5)0.0179 (6)−0.0010 (4)−0.0032 (4)−0.0052 (4)
C50.0145 (5)0.0167 (5)0.0173 (5)−0.0030 (4)−0.0019 (4)−0.0040 (4)
C60.0149 (5)0.0220 (6)0.0173 (6)−0.0031 (4)−0.0022 (4)−0.0061 (5)
C70.0200 (6)0.0256 (6)0.0220 (6)−0.0063 (5)−0.0016 (5)−0.0094 (5)
C80.0229 (6)0.0298 (7)0.0233 (6)−0.0040 (5)0.0005 (5)−0.0122 (5)
C90.0293 (7)0.0361 (8)0.0186 (6)−0.0058 (6)−0.0015 (5)−0.0089 (6)
C100.0281 (7)0.0281 (7)0.0174 (6)−0.0060 (5)−0.0027 (5)−0.0030 (5)
C110.0229 (6)0.0219 (6)0.0187 (6)−0.0008 (5)−0.0053 (5)−0.0039 (5)
C120.0214 (6)0.0183 (6)0.0193 (6)−0.0045 (4)−0.0017 (4)−0.0037 (5)
C130.0165 (5)0.0208 (6)0.0182 (6)−0.0032 (4)−0.0038 (4)−0.0059 (5)
C140.0206 (6)0.0223 (7)0.0317 (7)0.0018 (5)−0.0012 (5)−0.0069 (5)
C150.0231 (6)0.0203 (6)0.0196 (6)−0.0047 (5)0.0010 (5)−0.0066 (5)
C160.0215 (6)0.0215 (6)0.0292 (7)−0.0031 (5)−0.0018 (5)−0.0110 (5)
Geometric parameters (Å, º) top
Cl1—C121.801 (1)C4—C51.545 (2)
O1—C121.410 (2)C4—H40.96 (2)
O1—N11.476 (1)C5—C131.514 (2)
O2—C131.343 (1)C5—C121.549 (2)
O2—C141.456 (2)C5—C61.590 (2)
O3—C131.203 (1)C6—C71.534 (2)
O4—C151.299 (2)C6—C111.565 (2)
O4—H4O0.94 (3)C6—H60.96 (2)
O5—C151.218 (2)C7—C81.533 (2)
O6—C161.219 (2)C7—H710.96 (2)
O7—C161.282 (2)C7—H721.00 (2)
O7—H7O1.22 (2)C8—C91.527 (2)
O1W—H1W0.86 (2)C8—H810.97 (2)
O1W—H2W0.83 (2)C8—H820.97 (2)
N1—C11.490 (2)C9—C101.533 (2)
N1—C41.516 (2)C9—H910.96 (2)
N1—H7O1.34 (2)C9—H920.98 (2)
C1—C21.526 (2)C10—C111.533 (2)
C1—H0110.98 (2)C10—H1010.95 (2)
C1—H0120.96 (2)C10—H1021.00 (2)
C2—C31.541 (2)C11—C121.540 (2)
C2—H210.99 (2)C11—H110.96 (2)
C2—H220.98 (2)C14—H1410.97 (2)
C3—C41.544 (2)C14—H1420.92 (2)
C3—H310.98 (2)C14—H1430.99 (2)
C3—H320.98 (2)C15—C161.550 (2)
C12—O1—N1106.47 (8)C6—C7—H71106.0 (10)
C13—O2—C14115.94 (10)C8—C7—H72112.1 (9)
C15—O4—H4O109.2 (14)C6—C7—H72109.4 (9)
C16—O7—H7O109.4 (11)H71—C7—H72106.6 (13)
H1W—O1W—H2W109 (2)C9—C8—C7110.94 (11)
O1—N1—C1105.85 (9)C9—C8—H81107.4 (9)
O1—N1—C4104.78 (8)C7—C8—H81111.3 (9)
C1—N1—C4106.68 (9)C9—C8—H82112.5 (10)
O1—N1—H7O110.8 (10)C7—C8—H82107.6 (10)
C1—N1—H7O113.1 (10)H81—C8—H82107.1 (13)
C4—N1—H7O114.9 (10)C8—C9—C10109.93 (11)
N1—C1—C2105.03 (10)C8—C9—H91111.0 (10)
N1—C1—H011104.9 (9)C10—C9—H91109.8 (11)
C2—C1—H011109.9 (9)C8—C9—H92110.7 (10)
N1—C1—H012110.4 (10)C10—C9—H92110.6 (10)
C2—C1—H012115.3 (10)H91—C9—H92104.6 (15)
H011—C1—H012110.6 (13)C11—C10—C9110.96 (11)
C1—C2—C3101.90 (10)C11—C10—H101108.7 (9)
C1—C2—H21108.3 (9)C9—C10—H101108.3 (9)
C3—C2—H21112.4 (9)C11—C10—H102109.3 (10)
C1—C2—H22110.4 (11)C9—C10—H102112.1 (11)
C3—C2—H22112.5 (10)H101—C10—H102107.3 (14)
H21—C2—H22110.8 (14)C10—C11—C12115.46 (11)
C2—C3—C4105.01 (10)C10—C11—C6114.49 (11)
C2—C3—H31109.5 (9)C12—C11—C686.74 (9)
C4—C3—H31109.3 (9)C10—C11—H11111.7 (10)
C2—C3—H32114.2 (9)C12—C11—H11111.6 (10)
C4—C3—H32112.0 (9)C6—C11—H11114.8 (10)
H31—C3—H32106.8 (13)O1—C12—C11109.23 (10)
N1—C4—C3106.00 (9)O1—C12—C5103.35 (9)
N1—C4—C5103.60 (9)C11—C12—C592.32 (9)
C3—C4—C5117.43 (10)O1—C12—Cl1109.52 (8)
N1—C4—H4108.3 (9)C11—C12—Cl1119.37 (9)
C3—C4—H4110.9 (9)C5—C12—Cl1121.05 (9)
C5—C4—H4109.9 (9)O3—C13—O2123.94 (11)
C13—C5—C4112.30 (10)O3—C13—C5127.02 (11)
C13—C5—C12120.05 (10)O2—C13—C5109.02 (10)
C4—C5—C12105.36 (9)O2—C14—H141109.6 (11)
C13—C5—C6113.31 (10)O2—C14—H142110.3 (11)
C4—C5—C6117.89 (9)H141—C14—H142110.4 (15)
C12—C5—C685.55 (9)O2—C14—H143104.8 (10)
C7—C6—C11118.41 (10)H141—C14—H143111.8 (15)
C7—C6—C5122.38 (10)H142—C14—H143109.8 (15)
C11—C6—C589.80 (9)O5—C15—O4126.07 (12)
C7—C6—H6108.7 (9)O5—C15—C16119.35 (11)
C11—C6—H6108.9 (9)O4—C15—C16114.58 (11)
C5—C6—H6106.9 (9)O6—C16—O7126.40 (12)
C8—C7—C6114.62 (11)O6—C16—C15117.18 (12)
C8—C7—H71107.7 (10)O7—C16—C15116.39 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7O···N11.22 (2)1.34 (2)2.5690 (14)179 (2)
O4—H4O···O1W0.94 (3)1.63 (3)2.5589 (14)169 (2)
O1W—H1W···O5i0.86 (2)1.94 (2)2.7917 (14)168 (2)
O1W—H2W···O6ii0.83 (2)1.95 (2)2.6886 (15)147 (2)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC14H20ClNO3·C2H2O4·H2O
Mr393.81
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)6.6133 (2), 8.0737 (2), 17.8848 (5)
α, β, γ (°)77.746 (1), 83.211 (1), 80.169 (1)
V (Å3)916.14 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.25
Crystal size (mm)0.42 × 0.35 × 0.17
Data collection
DiffractometerBruker SMART-CCD 1K
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		11202, 4763, 3835
Rint0.026
(sin θ/λ)max (Å−1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.085, 1.02
No. of reflections4763
No. of parameters331
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.39, −0.28

Computer programs: SMART (Bruker, 1997), SMART, SHELXTL (Bruker, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7O···N11.22 (2)1.34 (2)2.5690 (14)179 (2)
O4—H4O···O1W0.94 (3)1.63 (3)2.5589 (14)169 (2)
O1W—H1W···O5i0.86 (2)1.94 (2)2.7917 (14)168 (2)
O1W—H2W···O6ii0.83 (2)1.95 (2)2.6886 (15)147 (2)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, y, z.
 

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