organic compounds
The title compound, C10H13N3O5, was designed as a potential endothelin receptor antagonist and as a probe of the structural requirements of the endothelin receptor binding site. The isoxazole ring is planar and the cyclononane moiety lies approximately in the plane of the heterocycle. The molecules are packed in the crystal structure by ionic and van der Waals interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004186/hg6133sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004186/hg6133IIsup2.hkl |
CCDC reference: 270427
Computing details top
Data collection: XSCANS (Siemens, 1991); 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: PLUTON (Spek, 1992); software used to prepare material for publication: SHELXL97.
4,4-Dinitro-5,6,7,8,9,10-hexahydro-4H-cyclonona[d]isoxazole top
Crystal data top
C10H13N3O5 | F(000) = 536 |
Mr = 255.23 | Dx = 1.461 Mg m−3 |
Monoclinic, P21/n | Melting point: 375 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.735 (2) Å | Cell parameters from 20 reflections |
b = 16.569 (4) Å | θ = 7–20° |
c = 8.764 (2) Å | µ = 0.12 mm−1 |
β = 113.81 (4)° | T = 293 K |
V = 1160.5 (5) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.20 × 0.15 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.039 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 2.5° |
Graphite monochromator | h = 0→12 |
ω/2θ scans | k = 0→23 |
3583 measured reflections | l = −12→11 |
3383 independent reflections | 3 standard reflections every 97 reflections |
1421 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.162 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0694P)2] where P = (Fo2 + 2Fc2)/3 |
3383 reflections | (Δ/σ)max = 0.001 |
163 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.9096 (2) | −0.05376 (10) | −0.2294 (2) | 0.0662 (5) | |
N2 | 0.7924 (3) | −0.09898 (12) | −0.1923 (3) | 0.0718 (6) | |
C3 | 0.6943 (3) | −0.04550 (14) | −0.1733 (3) | 0.0594 (6) | |
H3 | 0.6042 | −0.0582 | −0.1469 | 0.071* | |
C3A | 0.7373 (2) | 0.03438 (12) | −0.1966 (2) | 0.0427 (5) | |
C4 | 0.6522 (2) | 0.10938 (12) | −0.1786 (2) | 0.0427 (5) | |
C5 | 0.6752 (3) | 0.18516 (14) | −0.2641 (3) | 0.0582 (6) | |
H5A | 0.7936 | 0.1976 | −0.2231 | 0.070* | |
H5B | 0.6204 | 0.2299 | −0.2352 | 0.070* | |
C6 | 0.6041 (4) | 0.1769 (3) | −0.4540 (4) | 0.1237 (16) | |
H6A | 0.5645 | 0.1217 | −0.4790 | 0.148* | |
H6B | 0.5056 | 0.2110 | −0.4975 | 0.148* | |
C7 | 0.6907 (6) | 0.1922 (4) | −0.5451 (4) | 0.175 (3) | |
H7A | 0.6624 | 0.2471 | −0.5846 | 0.211* | |
H7B | 0.6425 | 0.1579 | −0.6427 | 0.211* | |
C8 | 0.8713 (5) | 0.18582 (18) | −0.4916 (4) | 0.0915 (10) | |
H8A | 0.9233 | 0.2216 | −0.3970 | 0.110* | |
H8B | 0.8988 | 0.2063 | −0.5811 | 0.110* | |
C9 | 0.9512 (3) | 0.10494 (16) | −0.4434 (3) | 0.0662 (7) | |
H9A | 1.0527 | 0.1045 | −0.4632 | 0.079* | |
H9B | 0.8762 | 0.0649 | −0.5166 | 0.079* | |
C10 | 0.9959 (3) | 0.07882 (17) | −0.2630 (3) | 0.0644 (7) | |
H10A | 1.1027 | 0.0511 | −0.2236 | 0.077* | |
H10B | 1.0113 | 0.1271 | −0.1958 | 0.077* | |
C10A | 0.8748 (3) | 0.02586 (14) | −0.2312 (2) | 0.0479 (5) | |
N3 | 0.7033 (2) | 0.12410 (13) | 0.0101 (2) | 0.0566 (5) | |
O2 | 0.7829 (3) | 0.18347 (12) | 0.0707 (2) | 0.0890 (6) | |
O3 | 0.6669 (2) | 0.07114 (12) | 0.0864 (2) | 0.0804 (6) | |
N4 | 0.4612 (2) | 0.09592 (12) | −0.2430 (3) | 0.0584 (5) | |
O4 | 0.3978 (2) | 0.04630 (11) | −0.3503 (2) | 0.0764 (6) | |
O5 | 0.3870 (2) | 0.13998 (12) | −0.1852 (3) | 0.0970 (7) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0668 (11) | 0.0693 (12) | 0.0659 (11) | 0.0265 (9) | 0.0302 (9) | 0.0065 (8) |
N2 | 0.0817 (15) | 0.0538 (13) | 0.0858 (16) | 0.0116 (11) | 0.0400 (13) | 0.0063 (11) |
C3 | 0.0619 (15) | 0.0566 (15) | 0.0647 (15) | 0.0043 (12) | 0.0308 (12) | −0.0024 (12) |
C3A | 0.0429 (11) | 0.0478 (12) | 0.0391 (10) | 0.0011 (9) | 0.0182 (9) | −0.0037 (9) |
C4 | 0.0394 (11) | 0.0447 (12) | 0.0460 (11) | −0.0032 (9) | 0.0192 (9) | −0.0048 (9) |
C5 | 0.0581 (14) | 0.0529 (14) | 0.0597 (15) | −0.0053 (11) | 0.0198 (12) | 0.0087 (11) |
C6 | 0.083 (2) | 0.180 (4) | 0.070 (2) | −0.056 (2) | −0.0094 (17) | 0.056 (2) |
C7 | 0.150 (4) | 0.320 (7) | 0.0483 (19) | 0.136 (4) | 0.031 (2) | 0.020 (3) |
C8 | 0.160 (3) | 0.0715 (19) | 0.0659 (18) | −0.007 (2) | 0.069 (2) | 0.0083 (14) |
C9 | 0.0623 (16) | 0.0845 (19) | 0.0634 (15) | 0.0002 (13) | 0.0374 (13) | 0.0105 (14) |
C10 | 0.0402 (12) | 0.0947 (19) | 0.0598 (14) | 0.0044 (12) | 0.0219 (11) | 0.0129 (14) |
C10A | 0.0428 (11) | 0.0619 (15) | 0.0373 (10) | 0.0089 (11) | 0.0144 (9) | 0.0050 (10) |
N3 | 0.0669 (13) | 0.0582 (12) | 0.0565 (12) | −0.0025 (10) | 0.0370 (10) | −0.0076 (10) |
O2 | 0.1187 (17) | 0.0799 (13) | 0.0699 (12) | −0.0293 (12) | 0.0397 (12) | −0.0306 (10) |
O3 | 0.1062 (15) | 0.0857 (13) | 0.0730 (12) | −0.0052 (11) | 0.0609 (12) | 0.0073 (10) |
N4 | 0.0442 (11) | 0.0514 (12) | 0.0822 (14) | 0.0007 (9) | 0.0283 (11) | −0.0048 (11) |
O4 | 0.0506 (10) | 0.0742 (12) | 0.0918 (13) | −0.0108 (9) | 0.0157 (9) | −0.0210 (11) |
O5 | 0.0591 (12) | 0.0913 (15) | 0.151 (2) | 0.0092 (10) | 0.0532 (13) | −0.0345 (13) |
Geometric parameters (Å, º) top
O1—C10A | 1.352 (3) | C7—C8 | 1.457 (5) |
O1—N2 | 1.408 (3) | C7—H7A | 0.9700 |
N2—C3 | 1.289 (3) | C7—H7B | 0.9700 |
C3—C3A | 1.413 (3) | C8—C9 | 1.491 (4) |
C3—H3 | 0.9300 | C8—H8A | 0.9700 |
C3A—C10A | 1.360 (3) | C8—H8B | 0.9700 |
C3A—C4 | 1.489 (3) | C9—C10 | 1.530 (3) |
C4—C5 | 1.516 (3) | C9—H9A | 0.9700 |
C4—N4 | 1.547 (3) | C9—H9B | 0.9700 |
C4—N3 | 1.549 (3) | C10—C10A | 1.484 (3) |
C5—C6 | 1.530 (4) | C10—H10A | 0.9700 |
C5—H5A | 0.9700 | C10—H10B | 0.9700 |
C5—H5B | 0.9700 | N3—O2 | 1.198 (2) |
C6—C7 | 1.327 (5) | N3—O3 | 1.220 (2) |
C6—H6A | 0.9700 | N4—O4 | 1.202 (2) |
C6—H6B | 0.9700 | N4—O5 | 1.214 (2) |
C10A—O1—N2 | 109.97 (16) | C8—C7—H7B | 105.6 |
C3—N2—O1 | 104.29 (19) | H7A—C7—H7B | 106.1 |
N2—C3—C3A | 113.3 (2) | C7—C8—C9 | 118.6 (3) |
N2—C3—H3 | 123.3 | C7—C8—H8A | 107.7 |
C3A—C3—H3 | 123.3 | C9—C8—H8A | 107.7 |
C10A—C3A—C3 | 104.18 (19) | C7—C8—H8B | 107.7 |
C10A—C3A—C4 | 129.34 (19) | C9—C8—H8B | 107.7 |
C3—C3A—C4 | 126.43 (18) | H8A—C8—H8B | 107.1 |
C3A—C4—C5 | 117.88 (17) | C8—C9—C10 | 116.2 (2) |
C3A—C4—N4 | 110.61 (16) | C8—C9—H9A | 108.2 |
C5—C4—N4 | 106.14 (17) | C10—C9—H9A | 108.2 |
C3A—C4—N3 | 107.67 (16) | C8—C9—H9B | 108.2 |
C5—C4—N3 | 111.01 (17) | C10—C9—H9B | 108.2 |
N4—C4—N3 | 102.45 (16) | H9A—C9—H9B | 107.4 |
C4—C5—C6 | 112.7 (2) | C10A—C10—C9 | 117.2 (2) |
C4—C5—H5A | 109.0 | C10A—C10—H10A | 108.0 |
C6—C5—H5A | 109.0 | C9—C10—H10A | 108.0 |
C4—C5—H5B | 109.0 | C10A—C10—H10B | 108.0 |
C6—C5—H5B | 109.0 | C9—C10—H10B | 108.0 |
H5A—C5—H5B | 107.8 | H10A—C10—H10B | 107.2 |
C7—C6—C5 | 123.9 (3) | O1—C10A—C3A | 108.2 (2) |
C7—C6—H6A | 106.4 | O1—C10A—C10 | 113.95 (19) |
C5—C6—H6A | 106.4 | C3A—C10A—C10 | 137.8 (2) |
C7—C6—H6B | 106.4 | O2—N3—O3 | 125.5 (2) |
C5—C6—H6B | 106.4 | O2—N3—C4 | 117.92 (19) |
H6A—C6—H6B | 106.4 | O3—N3—C4 | 116.43 (19) |
C6—C7—C8 | 126.8 (3) | O4—N4—O5 | 125.6 (2) |
C6—C7—H7A | 105.6 | O4—N4—C4 | 118.16 (18) |
C8—C7—H7A | 105.6 | O5—N4—C4 | 116.09 (19) |
C6—C7—H7B | 105.6 | ||
C10A—O1—N2—C3 | −0.2 (3) | N2—O1—C10A—C10 | 177.79 (17) |
O1—N2—C3—C3A | 0.4 (3) | C3—C3A—C10A—O1 | 0.3 (2) |
N2—C3—C3A—C10A | −0.5 (3) | C4—C3A—C10A—O1 | 177.83 (19) |
N2—C3—C3A—C4 | −178.1 (2) | C3—C3A—C10A—C10 | −176.8 (2) |
C10A—C3A—C4—C5 | 23.7 (3) | C4—C3A—C10A—C10 | 0.7 (4) |
C3—C3A—C4—C5 | −159.3 (2) | C9—C10—C10A—O1 | 94.6 (2) |
C10A—C3A—C4—N4 | 146.1 (2) | C9—C10—C10A—C3A | −88.4 (3) |
C3—C3A—C4—N4 | −37.0 (3) | C3A—C4—N3—O2 | 115.7 (2) |
C10A—C3A—C4—N3 | −102.7 (2) | C5—C4—N3—O2 | −14.7 (3) |
C3—C3A—C4—N3 | 74.2 (3) | N4—C4—N3—O2 | −127.6 (2) |
C3A—C4—C5—C6 | 63.0 (3) | C3A—C4—N3—O3 | −60.1 (2) |
N4—C4—C5—C6 | −61.6 (3) | C5—C4—N3—O3 | 169.55 (19) |
N3—C4—C5—C6 | −172.2 (2) | N4—C4—N3—O3 | 56.6 (2) |
C4—C5—C6—C7 | −127.1 (5) | C3A—C4—N4—O4 | −28.1 (3) |
C5—C6—C7—C8 | 27.7 (9) | C5—C4—N4—O4 | 100.9 (2) |
C6—C7—C8—C9 | 63.6 (7) | N3—C4—N4—O4 | −142.6 (2) |
C7—C8—C9—C10 | −85.1 (3) | C3A—C4—N4—O5 | 155.4 (2) |
C8—C9—C10—C10A | 96.9 (3) | C5—C4—N4—O5 | −75.6 (2) |
N2—O1—C10A—C3A | −0.1 (2) | N3—C4—N4—O5 | 40.9 (2) |