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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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.056
- wR factor = 0.162
- Data-to-parameter ratio = 20.8
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT241_ALERT_2_A Check High Ueq as Compared to Neighbors for C7
Author Response: This is caused by unresolved disorder of C7; for more details, see _publ_section_exptl_refinement |
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.12 Ratio PLAT230_ALERT_2_B Hirshfeld Test Diff for C5 - C6 .. 7.53 su PLAT230_ALERT_2_B Hirshfeld Test Diff for C6 - C7 .. 10.29 su PLAT360_ALERT_2_B Short C(sp3)-C(sp3) Bond C6 - C7 ... 1.33 Ang.
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.01 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - N2 .. 5.28 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C3A .. 5.81 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT320_ALERT_2_C Check Hybridisation of C7 in Main Residue . ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C10 H13 N3 O5
1 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
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) |
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