4,4-Dinitro-5,6,7,8,9,10-hexa­hydro-4H-cyclo­nona­[d]isoxazole

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	Prism, colourless
Z = 4	0.30 × 0.20 × 0.15 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0694P)^2] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)