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In the title compound, C
17H
20N
2O
3, the cyclobutane ring is puckered, with a dihedral angle of 19.11 (15)°. The 1-phenyl and 3-[1-hydroxyimino-2-(succinimido)ethyl] groups are in
cis positions. The molecules are linked by O-H
O and C-H
(benzene) interactions, forming a two-dimensional network.
Supporting information
CCDC reference: 251328
A mixture of 1-phenyl-1-methyl-3-(2-succinimido-1-oxoethyl)cyclobutane (2.853 g, 0.01 mol), synthesized according to the literature method of Ahmedzade et al. (2003), hydroxylamine hydrochloride (0.695 g, 0.01 mol) and pyridine (5 ml) in ethanol (100 ml) was refluxed for 3 h. The solvent was removed by distillation, and the resulting solid was filtered off, washed with cold water, dried and recrystallized from ethanol to obtain the title compound (yield 2.8 g, 85%; m.p. 426 K). Elemental analysis calculated for C17H20N2O3: C 67.98, H 6.71, N 9.33%; found: C 68.02, H 6.84, N 9.45%. IR spectroscopy (KBr pellet, ν, cm−1): 1620 (C═N), 3253 (–OH oxime). 1H NMR (CDCl3, δ, p.p.m.): 7.10–7.30 (m, 5H, aromatics), 4.4 (s, 2H, CH2 cyclobutane), 3.5 (quint, 1H, J = 8.9 Hz, CH cyclobutane), 1.74–2.75 (m, 8H, CH2 cyclobutane plus succinimide), 1.49 (s, 3H, CH3).
The oxime H atom was located from a difference density map and the other H atoms were positioned geometrically. All H atoms were treated using a riding model, with an O—H distance of 0.82 Å and C—H distances of 0.93–0.98 Å, and with Uiso(H) = 1.2Ueq (1.5Ueq for methyl) of the parent atom. The maximum difference density (0.73 e Å−3) is located 0.70 Å from atom C3, and the minimum difference density (−0.74 e Å−3) is 0.59 Å from atom C11.
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
1-Methyl-1-phenyl-3-[1-hydroxyimino-2-(succinimido)ethyl]cyclobutane
top
Crystal data top
C17H20N2O3 | F(000) = 640 |
Mr = 300.35 | Dx = 1.281 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 12629 reflections |
a = 8.8356 (7) Å | θ = 1.3–26.1° |
b = 5.7520 (5) Å | µ = 0.09 mm−1 |
c = 30.803 (2) Å | T = 250 K |
β = 95.821 (6)° | Prism, colourless |
V = 1557.4 (2) Å3 | 0.63 × 0.53 × 0.35 mm |
Z = 4 | |
Data collection top
Stoe IPDS 2 diffractometer | 2179 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube | Rint = 0.062 |
Plane graphite monochromator | θmax = 25.0°, θmin = 2.3° |
Detector resolution: 6.67 pixels mm-1 | h = −10→10 |
w scans | k = −6→6 |
11598 measured reflections | l = −34→36 |
2694 independent reflections | |
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)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.112P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2694 reflections | Δρmax = 0.73 e Å−3 |
200 parameters | Δρmin = −0.74 e Å−3 |
0 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: 0.027 (6) |
Crystal data top
C17H20N2O3 | V = 1557.4 (2) Å3 |
Mr = 300.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.8356 (7) Å | µ = 0.09 mm−1 |
b = 5.7520 (5) Å | T = 250 K |
c = 30.803 (2) Å | 0.63 × 0.53 × 0.35 mm |
β = 95.821 (6)° | |
Data collection top
Stoe IPDS 2 diffractometer | 2179 reflections with I > 2σ(I) |
11598 measured reflections | Rint = 0.062 |
2694 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.73 e Å−3 |
2694 reflections | Δρmin = −0.74 e Å−3 |
200 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 | Uiso*/Ueq | |
O1 | 0.57548 (13) | 1.1129 (2) | 0.23301 (5) | 0.0624 (4) | |
H1 | 0.6667 | 1.1301 | 0.2402 | 0.094* | |
O2 | 0.11958 (13) | 0.6729 (2) | 0.24004 (5) | 0.0624 (4) | |
O3 | 0.09359 (17) | 1.2749 (3) | 0.14455 (5) | 0.0717 (4) | |
N1 | 0.55473 (14) | 0.9532 (3) | 0.19850 (5) | 0.0489 (4) | |
N2 | 0.13975 (13) | 0.9843 (2) | 0.19487 (4) | 0.0385 (3) | |
C1 | 0.47200 (17) | 0.6567 (3) | 0.08929 (5) | 0.0390 (4) | |
C2 | 0.48672 (18) | 0.5782 (3) | 0.13774 (6) | 0.0434 (4) | |
H2A | 0.4502 | 0.4215 | 0.1419 | 0.052* | |
H2B | 0.5879 | 0.5992 | 0.1526 | 0.052* | |
C3 | 0.37278 (16) | 0.7693 (3) | 0.14827 (5) | 0.0418 (4) | |
H3 | 0.2701 | 0.7055 | 0.1487 | 0.050* | |
C4 | 0.39321 (19) | 0.8815 (3) | 0.10328 (6) | 0.0473 (4) | |
H4A | 0.2979 | 0.9151 | 0.0859 | 0.057* | |
H4B | 0.4592 | 1.0167 | 0.1052 | 0.057* | |
C5 | 0.06559 (16) | 0.7988 (3) | 0.21082 (6) | 0.0422 (4) | |
C6 | −0.08827 (17) | 0.7771 (3) | 0.18585 (6) | 0.0481 (4) | |
H6A | −0.1675 | 0.7790 | 0.2055 | 0.058* | |
H6B | −0.0960 | 0.6339 | 0.1692 | 0.058* | |
C7 | −0.10169 (19) | 0.9863 (3) | 0.15585 (6) | 0.0511 (5) | |
H7A | −0.1241 | 0.9382 | 0.1257 | 0.061* | |
H7B | −0.1817 | 1.0896 | 0.1634 | 0.061* | |
C8 | 0.05026 (18) | 1.1044 (3) | 0.16255 (6) | 0.0449 (4) | |
C9 | 0.29534 (16) | 1.0509 (3) | 0.20969 (6) | 0.0420 (4) | |
H9A | 0.3137 | 1.0219 | 0.2408 | 0.050* | |
H9B | 0.3069 | 1.2165 | 0.2051 | 0.050* | |
C10 | 0.41363 (16) | 0.9229 (3) | 0.18684 (5) | 0.0386 (4) | |
C11 | 0.3634 (2) | 0.5056 (3) | 0.05978 (7) | 0.0538 (5) | |
H11A | 0.2699 | 0.4864 | 0.0727 | 0.081* | |
H11B | 0.4089 | 0.3561 | 0.0562 | 0.081* | |
H11C | 0.3431 | 0.5790 | 0.0318 | 0.081* | |
C12 | 0.62057 (17) | 0.6868 (3) | 0.06964 (5) | 0.0388 (4) | |
C13 | 0.6486 (2) | 0.8772 (3) | 0.04414 (6) | 0.0498 (4) | |
H13 | 0.5745 | 0.9915 | 0.0389 | 0.060* | |
C14 | 0.7856 (2) | 0.8995 (4) | 0.02626 (7) | 0.0645 (6) | |
H14 | 0.8022 | 1.0276 | 0.0089 | 0.077* | |
C15 | 0.8970 (2) | 0.7336 (4) | 0.03394 (7) | 0.0679 (6) | |
H15 | 0.9893 | 0.7502 | 0.0222 | 0.081* | |
C16 | 0.8716 (2) | 0.5443 (4) | 0.05893 (7) | 0.0617 (5) | |
H16 | 0.9466 | 0.4313 | 0.0641 | 0.074* | |
C17 | 0.7339 (2) | 0.5200 (3) | 0.07668 (6) | 0.0488 (4) | |
H17 | 0.7175 | 0.3899 | 0.0935 | 0.059* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0343 (6) | 0.0811 (9) | 0.0709 (9) | −0.0085 (6) | 0.0010 (6) | −0.0336 (7) |
O2 | 0.0361 (6) | 0.0784 (9) | 0.0716 (9) | 0.0017 (6) | 0.0009 (6) | 0.0308 (7) |
O3 | 0.0647 (9) | 0.0677 (9) | 0.0820 (11) | −0.0027 (7) | 0.0041 (7) | 0.0286 (8) |
N1 | 0.0312 (7) | 0.0637 (9) | 0.0522 (9) | −0.0050 (6) | 0.0061 (6) | −0.0148 (7) |
N2 | 0.0264 (6) | 0.0478 (7) | 0.0414 (8) | 0.0027 (5) | 0.0049 (5) | 0.0001 (5) |
C1 | 0.0387 (8) | 0.0389 (7) | 0.0396 (9) | 0.0022 (6) | 0.0050 (6) | −0.0034 (6) |
C2 | 0.0463 (9) | 0.0412 (8) | 0.0439 (10) | 0.0024 (6) | 0.0105 (7) | 0.0009 (6) |
C3 | 0.0323 (7) | 0.0489 (9) | 0.0449 (9) | −0.0029 (6) | 0.0077 (6) | −0.0080 (7) |
C4 | 0.0493 (9) | 0.0475 (9) | 0.0448 (10) | 0.0122 (7) | 0.0024 (7) | −0.0031 (7) |
C5 | 0.0291 (7) | 0.0506 (9) | 0.0477 (10) | 0.0038 (6) | 0.0070 (6) | 0.0056 (7) |
C6 | 0.0293 (7) | 0.0545 (9) | 0.0599 (11) | 0.0001 (6) | 0.0019 (7) | 0.0007 (8) |
C7 | 0.0353 (8) | 0.0673 (11) | 0.0492 (11) | 0.0072 (7) | −0.0026 (7) | 0.0031 (8) |
C8 | 0.0405 (8) | 0.0498 (9) | 0.0447 (10) | 0.0056 (7) | 0.0062 (7) | 0.0028 (7) |
C9 | 0.0286 (8) | 0.0493 (8) | 0.0485 (10) | −0.0021 (6) | 0.0054 (6) | −0.0089 (7) |
C10 | 0.0291 (7) | 0.0469 (8) | 0.0408 (9) | −0.0031 (6) | 0.0075 (6) | −0.0023 (6) |
C11 | 0.0483 (10) | 0.0572 (10) | 0.0554 (12) | −0.0046 (8) | 0.0037 (8) | −0.0111 (8) |
C12 | 0.0417 (8) | 0.0403 (8) | 0.0345 (8) | −0.0013 (6) | 0.0041 (6) | −0.0039 (6) |
C13 | 0.0588 (10) | 0.0470 (9) | 0.0438 (10) | 0.0004 (7) | 0.0065 (7) | 0.0031 (7) |
C14 | 0.0750 (13) | 0.0653 (12) | 0.0562 (13) | −0.0174 (10) | 0.0206 (10) | 0.0047 (9) |
C15 | 0.0510 (11) | 0.0889 (15) | 0.0677 (14) | −0.0137 (10) | 0.0249 (9) | −0.0107 (11) |
C16 | 0.0476 (10) | 0.0747 (12) | 0.0646 (13) | 0.0091 (9) | 0.0145 (9) | −0.0064 (10) |
C17 | 0.0472 (9) | 0.0503 (9) | 0.0503 (11) | 0.0064 (7) | 0.0121 (7) | 0.0020 (7) |
Geometric parameters (Å, º) top
O1—N1 | 1.4030 (18) | C6—H6A | 0.9700 |
O1—H1 | 0.8200 | C6—H6B | 0.9700 |
O2—C5 | 1.214 (2) | C7—C8 | 1.500 (2) |
O3—C8 | 1.208 (2) | C7—H7A | 0.9700 |
N1—C10 | 1.274 (2) | C7—H7B | 0.9700 |
N2—C5 | 1.369 (2) | C9—C10 | 1.510 (2) |
N2—C8 | 1.391 (2) | C9—H9A | 0.9700 |
N2—C9 | 1.4552 (18) | C9—H9B | 0.9700 |
C1—C12 | 1.510 (2) | C11—H11A | 0.9600 |
C1—C11 | 1.525 (2) | C11—H11B | 0.9600 |
C1—C4 | 1.550 (2) | C11—H11C | 0.9600 |
C1—C2 | 1.552 (2) | C12—C13 | 1.385 (2) |
C2—C3 | 1.547 (2) | C12—C17 | 1.388 (2) |
C2—H2A | 0.9700 | C13—C14 | 1.386 (3) |
C2—H2B | 0.9700 | C13—H13 | 0.9300 |
C3—C10 | 1.495 (2) | C14—C15 | 1.375 (3) |
C3—C4 | 1.556 (2) | C14—H14 | 0.9300 |
C3—H3 | 0.9800 | C15—C16 | 1.365 (3) |
C4—H4A | 0.9700 | C15—H15 | 0.9300 |
C4—H4B | 0.9700 | C16—C17 | 1.391 (3) |
C5—C6 | 1.498 (2) | C16—H16 | 0.9300 |
C6—C7 | 1.514 (3) | C17—H17 | 0.9300 |
| | | |
N1—O1—H1 | 109.5 | C6—C7—H7A | 110.7 |
C10—N1—O1 | 110.61 (13) | C8—C7—H7B | 110.7 |
C5—N2—C8 | 112.71 (13) | C6—C7—H7B | 110.7 |
C5—N2—C9 | 124.33 (13) | H7A—C7—H7B | 108.8 |
C8—N2—C9 | 122.96 (13) | O3—C8—N2 | 123.25 (15) |
C12—C1—C11 | 110.26 (14) | O3—C8—C7 | 128.73 (16) |
C12—C1—C4 | 116.66 (13) | N2—C8—C7 | 108.02 (14) |
C11—C1—C4 | 111.60 (13) | N2—C9—C10 | 113.71 (12) |
C12—C1—C2 | 115.30 (12) | N2—C9—H9A | 108.8 |
C11—C1—C2 | 113.17 (14) | C10—C9—H9A | 108.8 |
C4—C1—C2 | 88.39 (12) | N2—C9—H9B | 108.8 |
C3—C2—C1 | 90.11 (12) | C10—C9—H9B | 108.8 |
C3—C2—H2A | 113.6 | H9A—C9—H9B | 107.7 |
C1—C2—H2A | 113.6 | N1—C10—C3 | 117.08 (13) |
C3—C2—H2B | 113.6 | N1—C10—C9 | 120.40 (14) |
C1—C2—H2B | 113.6 | C3—C10—C9 | 122.40 (12) |
H2A—C2—H2B | 110.9 | C1—C11—H11A | 109.5 |
C10—C3—C2 | 118.48 (13) | C1—C11—H11B | 109.5 |
C10—C3—C4 | 114.97 (13) | H11A—C11—H11B | 109.5 |
C2—C3—C4 | 88.35 (12) | C1—C11—H11C | 109.5 |
C10—C3—H3 | 111.1 | H11A—C11—H11C | 109.5 |
C2—C3—H3 | 111.1 | H11B—C11—H11C | 109.5 |
C4—C3—H3 | 111.1 | C13—C12—C17 | 117.90 (15) |
C1—C4—C3 | 89.85 (12) | C13—C12—C1 | 122.05 (14) |
C1—C4—H4A | 113.7 | C17—C12—C1 | 120.05 (14) |
C3—C4—H4A | 113.7 | C12—C13—C14 | 120.82 (17) |
C1—C4—H4B | 113.7 | C12—C13—H13 | 119.6 |
C3—C4—H4B | 113.7 | C14—C13—H13 | 119.6 |
H4A—C4—H4B | 110.9 | C15—C14—C13 | 120.44 (18) |
O2—C5—N2 | 124.36 (14) | C15—C14—H14 | 119.8 |
O2—C5—C6 | 126.78 (14) | C13—C14—H14 | 119.8 |
N2—C5—C6 | 108.85 (13) | C16—C15—C14 | 119.69 (17) |
C5—C6—C7 | 104.96 (13) | C16—C15—H15 | 120.2 |
C5—C6—H6A | 110.8 | C14—C15—H15 | 120.2 |
C7—C6—H6A | 110.8 | C15—C16—C17 | 120.15 (19) |
C5—C6—H6B | 110.8 | C15—C16—H16 | 119.9 |
C7—C6—H6B | 110.8 | C17—C16—H16 | 119.9 |
H6A—C6—H6B | 108.8 | C12—C17—C16 | 121.00 (17) |
C8—C7—C6 | 105.20 (13) | C12—C17—H17 | 119.5 |
C8—C7—H7A | 110.7 | C16—C17—H17 | 119.5 |
| | | |
C12—C1—C2—C3 | 132.62 (13) | C8—N2—C9—C10 | −94.48 (18) |
C11—C1—C2—C3 | −99.14 (14) | O1—N1—C10—C3 | 175.95 (14) |
C4—C1—C2—C3 | 13.72 (12) | O1—N1—C10—C9 | −0.2 (2) |
C1—C2—C3—C10 | −131.38 (14) | C2—C3—C10—N1 | 26.6 (2) |
C1—C2—C3—C4 | −13.67 (12) | C4—C3—C10—N1 | −75.92 (19) |
C12—C1—C4—C3 | −131.31 (13) | C2—C3—C10—C9 | −157.32 (15) |
C11—C1—C4—C3 | 100.70 (15) | C4—C3—C10—C9 | 100.17 (17) |
C2—C1—C4—C3 | −13.65 (12) | N2—C9—C10—N1 | −175.52 (15) |
C10—C3—C4—C1 | 134.54 (13) | N2—C9—C10—C3 | 8.5 (2) |
C2—C3—C4—C1 | 13.69 (12) | C11—C1—C12—C13 | 94.81 (18) |
C8—N2—C5—O2 | −177.81 (16) | C4—C1—C12—C13 | −33.8 (2) |
C9—N2—C5—O2 | 2.3 (3) | C2—C1—C12—C13 | −135.52 (16) |
C8—N2—C5—C6 | 3.31 (19) | C11—C1—C12—C17 | −84.77 (18) |
C9—N2—C5—C6 | −176.61 (14) | C4—C1—C12—C17 | 146.60 (15) |
O2—C5—C6—C7 | 176.13 (17) | C2—C1—C12—C17 | 44.9 (2) |
N2—C5—C6—C7 | −5.03 (19) | C17—C12—C13—C14 | 0.0 (3) |
C5—C6—C7—C8 | 4.77 (19) | C1—C12—C13—C14 | −179.53 (17) |
C5—N2—C8—O3 | 179.18 (17) | C12—C13—C14—C15 | −0.7 (3) |
C9—N2—C8—O3 | −0.9 (3) | C13—C14—C15—C16 | 0.8 (3) |
C5—N2—C8—C7 | −0.10 (19) | C14—C15—C16—C17 | −0.3 (3) |
C9—N2—C8—C7 | 179.83 (14) | C13—C12—C17—C16 | 0.5 (3) |
C6—C7—C8—O3 | 177.71 (19) | C1—C12—C17—C16 | −179.95 (17) |
C6—C7—C8—N2 | −3.06 (19) | C15—C16—C17—C12 | −0.4 (3) |
C5—N2—C9—C10 | 85.44 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···N2 | 0.98 | 2.50 | 2.9030 (19) | 104 |
C2—H2B···N1 | 0.97 | 2.51 | 2.879 (2) | 102 |
O1—H1···O2i | 0.82 | 1.94 | 2.7594 (16) | 177 |
C7—H7A···Cg3ii | 0.97 | 2.74 | 3.68 | 163 |
C11—H11C···Cg3iii | 0.96 | 3.12 | 3.71 | 121 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+1, −y+1, −z. |
Experimental details
Crystal data |
Chemical formula | C17H20N2O3 |
Mr | 300.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 250 |
a, b, c (Å) | 8.8356 (7), 5.7520 (5), 30.803 (2) |
β (°) | 95.821 (6) |
V (Å3) | 1557.4 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.63 × 0.53 × 0.35 |
|
Data collection |
Diffractometer | Stoe IPDS 2 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11598, 2694, 2179 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.146, 1.02 |
No. of reflections | 2694 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.73, −0.74 |
Selected geometric parameters (Å, º) topO1—N1 | 1.4030 (18) | C1—C12 | 1.510 (2) |
O2—C5 | 1.214 (2) | C1—C11 | 1.525 (2) |
O3—C8 | 1.208 (2) | C1—C4 | 1.550 (2) |
N1—C10 | 1.274 (2) | C1—C2 | 1.552 (2) |
N2—C5 | 1.369 (2) | C2—C3 | 1.547 (2) |
N2—C8 | 1.391 (2) | C3—C10 | 1.495 (2) |
N2—C9 | 1.4552 (18) | C3—C4 | 1.556 (2) |
| | | |
C10—N1—O1 | 110.61 (13) | C1—C4—C3 | 89.85 (12) |
C5—N2—C8 | 112.71 (13) | O2—C5—N2 | 124.36 (14) |
C5—N2—C9 | 124.33 (13) | O3—C8—N2 | 123.25 (15) |
C8—N2—C9 | 122.96 (13) | N2—C9—C10 | 113.71 (12) |
C4—C1—C2 | 88.39 (12) | N1—C10—C3 | 117.08 (13) |
C3—C2—C1 | 90.11 (12) | N1—C10—C9 | 120.40 (14) |
C2—C3—C4 | 88.35 (12) | C3—C10—C9 | 122.40 (12) |
| | | |
C5—N2—C9—C10 | 85.44 (19) | C4—C3—C10—N1 | −75.92 (19) |
C8—N2—C9—C10 | −94.48 (18) | C2—C3—C10—C9 | −157.32 (15) |
O1—N1—C10—C3 | 175.95 (14) | C4—C3—C10—C9 | 100.17 (17) |
O1—N1—C10—C9 | −0.2 (2) | N2—C9—C10—N1 | −175.52 (15) |
C2—C3—C10—N1 | 26.6 (2) | N2—C9—C10—C3 | 8.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···N2 | 0.98 | 2.50 | 2.9030 (19) | 104 |
C2—H2B···N1 | 0.97 | 2.51 | 2.879 (2) | 102 |
O1—H1···O2i | 0.82 | 1.94 | 2.7594 (16) | 177 |
C7—H7A···Cg3ii | 0.97 | 2.74 | 3.68 | 163 |
C11—H11C···Cg3iii | 0.96 | 3.12 | 3.71 | 121 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+1, −y+1, −z. |
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3-Substituted cyclobutane carboxylic acid derivatives exhibit antiinflammatory and antidepressant activities (Dehmlow & Schmidt, 1990), and also liquid crystal properties (Coghi et al., 1976). Oximes show geometric isomerism, due to the double bond between the N and C atoms (Mixich & Thiele, 1979; Migrdichian, 1957). Because of the significant differences in the physical, chemical and biological properties of the geometric isomers, determination of the configuration of these isomers is important (Mathison et al., 1989). Oximes and oxime ethers also have a broad pharmacological activity spectrum, encompassing antifungal, antibacterial, antidepressant and insecticidal activities, as well as activity as a nerve-gas antidote, depending on the pharmacophoric group of the molecule (Polak, 1982; Balsamo et al., 1990; Holan et al., 1984; Forman, 1964). The oxime (C═N—OH) group possesses stronger hydrogen-bonding capabilities than alcohols, phenols and carboxylic acids (Marsman et al., 1999). Hydrogen bonding plays a key role in molecular recognition in chemical engineering (Bertolasi et al., 1982; Gilli et al., 1983; Hökelek et al., 2001). As part of our ongoing study of the relationship between the molecular and crystal structures of cyclobutane and oxime derivatives, a crystal structure determination of the title compound, (I), has been undertaken and the results are presented here. \sch
Previously, we have reported the closely related compound 2-[2-hydroxyimino-2-(3-methyl-3-phenylcyclobutyl)ethyl]isoindole-1,3-dione, (II) (Özdemir et al., 2004). The main aim of the present investigation is to study the types of differences which are present in the structure of (I) compared with (II), and to determine the strength of the hydrogen-bonding capabilities of the oxime group.
Fig. 1 shows the molecular structure and conformation of (I), with the atomic numbering scheme. The structure of (I) can be described as being built from planar fragments, viz. a cyclobutane ring (C1—C4), an oxime group (C10/N1/O1), a succinimide ring (O2/O3/N2/C5/C6/C7/C8), a phenyl ring (C12—C17), and a four-atom bridge (C3/C10/C9/N2) linking the cyclobutane and succinimide rings. The maximum deviation of the succinimide ring from planarity is 0.0413 (13) Å for atom C6. The C3—C10—C9—N2 torsion angle is 8.5 (2)°, corresponding to a (+)-synperiplanar configuration, and the plane of the four-atom bridge is almost perpendicular to the succinimide ring (Table 1). The plane of these four atoms makes a dihedral angle of 76.19 (8)° with the mean plane of the cyclobutane ring.
Although close to planar, the cyclobutane ring is more puckered than in (II). The C4/C1/C2 plane forms a dihedral angle of 19.26 (17)° with the C2/C3/C4 plane [11.55 (3)° in (II); Özdemir et al., 2004]. The mean plane of the cyclobutane ring forms a dihedral angle of 81.62 (6)° with the plane of the succinimide ring. The oxime moiety has an E configuration, with a C3—C10—N1—O1 torsion angle of 175.95 (14)°, which corresponds to a (+)-antiperiplanar configuration. In this configuration, atom O1 acts as hydrogen-bond donor to atom O2 of the succimido group at (1 − x, 1/2 + y, 1/2 − z). The O···O distance is 2.7594 (16) Å, which is a little shorter than that in (II) [2.814 (3) Å]. In (I), the plane of the oxime moiety is twisted by 74.95 (13)° out of the mean plane of the cyclobutane ring, and it is almost coplanar with the four-atom bridge, with a dihedral angle of 3.2 (2)°. The bond lengths and angles of the oxime moiety in (I) are close to those in (II).
There are two weak intramolecular C—H···N interactions in (I) (Fig. 1). Each of these interactions forms a five-membered ring. As a point of difference from (II), two intermolecular C—H···π(phenyl) interactions are also observed (Fig. 2 and Table 2). The centroid (Cg3) of the C12—C17 ring acts as a single acceptor for both these C—H···π interactions. A two-dimensional network is formed by these O—H···O and C—H···π(phenyl) interactions. There are no intermolecular π–π interactions in the crystal of (I).