1,5-Di­acetyl-7,7-di­nitro-1,5-di­aza­cyclo­octan-3-one ethyl­ene acetal

The solid state structure of the title compound, C₁₂H₁₈N₄O₈, has been determined. There are two mol­ecules in the asymmetric unit that differ in the conformations of their eight-membered heterocyclic rings and in the orientations of the nitro groups.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.113
• Data-to-parameter ratio = 12.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



DIFF_020  Alert A _diffrn_standards_interval_count and
          _diffrn_standards_interval_time are missing. Number of measurements
          between standards or time (min) between standards.

DIFF_022  Alert A _diffrn_standards_decay_% is missing
          Percentage decrease in standards intensity.


 2 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 0 Alert Level C = Please check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001).

(I)

Crystal data

C12H18N4O8	F(000) = 1456
Mr = 346.30	Dx = 1.509 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 17.9560 (2) Å	Cell parameters from 7327 reflections
b = 9.7885 (1) Å	θ = 4.7–57.1°
c = 18.2898 (1) Å	µ = 1.11 mm^−1
β = 108.507 (1)°	T = 293 K
V = 3048.41 (5) Å^3	Irregular, colorless
Z = 8	0.24 × 0.21 × 0.10 mm

Data collection

Bruker SMART 6000 diffractometer	5243 independent reflections
Radiation source: normal-focus sealed tube	4537 reflections with I > 2σ(I)
Gobel mirrors monochromator	Rint = 0.037
φ and ω scans	θmax = 67.2°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −20→21
Tmin = 0.670, Tmax = 0.864	k = −11→10
21447 measured reflections	l = −21→20

Refinement

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: calc
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0766P)^2 + 0.2099P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.031
5243 reflections	Δρmax = 0.24 e Å^−3
438 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0109 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.42743 (7)	−0.11060 (11)	0.19079 (6)	0.0386 (3)
O1	0.41983 (8)	−0.33891 (11)	0.19762 (6)	0.0576 (3)
C1A	0.42568 (9)	−0.23866 (15)	0.15981 (8)	0.0439 (3)
C1B	0.43215 (11)	−0.25336 (18)	0.08050 (10)	0.0580 (4)
H1BA	0.4216	−0.3463	0.0637	0.087*
H1BB	0.4842	−0.2290	0.0814	0.087*
H1BC	0.3948	−0.1942	0.0456	0.087*
C2	0.44573 (8)	0.01345 (15)	0.15469 (8)	0.0422 (3)
H2A	0.4802	−0.0119	0.1254	0.051*
H2B	0.4750	0.0746	0.1954	0.051*
C3	0.37642 (9)	0.09305 (14)	0.10122 (7)	0.0425 (3)
O3B	0.34908 (6)	0.03889 (11)	0.02496 (5)	0.0510 (3)
O3A	0.40782 (7)	0.22463 (10)	0.09464 (6)	0.0528 (3)
C3B	0.38734 (11)	0.1139 (2)	−0.01965 (9)	0.0603 (4)
H3BA	0.3563	0.1149	−0.0738	0.072*
H3BB	0.4389	0.0767	−0.0141	0.072*
C3A	0.39297 (13)	0.2524 (2)	0.01490 (10)	0.0673 (5)
H3AA	0.4356	0.3042	0.0066	0.081*
H3AB	0.3443	0.3026	−0.0064	0.081*
C4	0.30342 (9)	0.10156 (16)	0.12752 (8)	0.0468 (3)
H4A	0.2756	0.1853	0.1074	0.056*
H4B	0.2689	0.0260	0.1047	0.056*
N5	0.31876 (7)	0.09854 (12)	0.21094 (6)	0.0412 (3)
O5	0.34809 (9)	0.19555 (13)	0.32704 (7)	0.0683 (4)
C5A	0.33779 (9)	0.20969 (15)	0.25836 (9)	0.0487 (3)
C5B	0.34548 (12)	0.34711 (17)	0.22506 (11)	0.0617 (4)
H5BA	0.3681	0.4106	0.2661	0.093*
H5BB	0.2945	0.3789	0.1945	0.093*
H5BC	0.3787	0.3397	0.1932	0.093*
C6	0.29502 (8)	−0.02417 (15)	0.24289 (8)	0.0437 (3)
H6A	0.2647	−0.0816	0.2007	0.052*
H6B	0.2610	0.0021	0.2724	0.052*
C7	0.36321 (8)	−0.10753 (13)	0.29462 (7)	0.0393 (3)
O7C	0.32586 (7)	−0.07127 (13)	0.40496 (6)	0.0625 (3)
N7B	0.38111 (8)	−0.06559 (12)	0.37977 (7)	0.0458 (3)
O7D	0.44718 (7)	−0.03346 (13)	0.41615 (6)	0.0606 (3)
N7A	0.33605 (8)	−0.25678 (13)	0.29879 (8)	0.0518 (3)
O7A	0.37928 (9)	−0.32760 (12)	0.34934 (8)	0.0704 (4)
O7B	0.27470 (8)	−0.29340 (13)	0.25285 (9)	0.0760 (4)
C8	0.43890 (8)	−0.10393 (14)	0.27372 (7)	0.0394 (3)
H8A	0.4670	−0.0205	0.2941	0.047*
H8B	0.4717	−0.1801	0.2988	0.047*
N11	0.02805 (7)	0.66909 (11)	0.47725 (6)	0.0423 (3)
O11	−0.08978 (8)	0.70490 (12)	0.49381 (8)	0.0630 (3)
C11B	0.01890 (13)	0.8139 (2)	0.58514 (10)	0.0712 (5)
H11A	−0.0207	0.8652	0.5982	0.107*
H11B	0.0552	0.8755	0.5736	0.107*
H11C	0.0465	0.7570	0.6279	0.107*
C11A	−0.01913 (11)	0.72617 (15)	0.51605 (9)	0.0499 (4)
C12	0.11346 (9)	0.66485 (14)	0.50892 (8)	0.0456 (3)
H12A	0.1306	0.5741	0.5002	0.055*
H12B	0.1279	0.6777	0.5643	0.055*
C13	0.15929 (8)	0.76938 (14)	0.47715 (8)	0.0440 (3)
O13A	0.12077 (6)	0.89664 (10)	0.46937 (6)	0.0495 (3)
O13B	0.23504 (7)	0.78607 (11)	0.53288 (7)	0.0588 (3)
C13A	0.18095 (11)	0.99748 (17)	0.49819 (12)	0.0662 (5)
H13A	0.1609	1.0774	0.5171	0.079*
H13B	0.2036	1.0252	0.4589	0.079*
C13B	0.23923 (12)	0.92232 (19)	0.56220 (12)	0.0717 (5)
H13C	0.2915	0.9600	0.5727	0.086*
H13D	0.2248	0.9252	0.6090	0.086*
C14	0.17408 (9)	0.72573 (16)	0.40271 (9)	0.0506 (4)
H14A	0.1837	0.8067	0.3764	0.061*
H14B	0.2212	0.6701	0.4158	0.061*
O15	0.05763 (7)	0.46438 (13)	0.28149 (7)	0.0643 (3)
N15	0.10951 (7)	0.64889 (12)	0.34989 (7)	0.0435 (3)
C15A	0.11566 (9)	0.51892 (16)	0.32618 (8)	0.0495 (4)
C15B	0.19200 (11)	0.4438 (2)	0.35666 (12)	0.0704 (5)
H15A	0.1863	0.3535	0.3351	0.106*
H15B	0.2066	0.4379	0.4118	0.106*
H15C	0.2320	0.4920	0.3426	0.106*
C16	0.03614 (8)	0.72121 (15)	0.31417 (8)	0.0430 (3)
H16A	0.0245	0.7197	0.2586	0.052*
H16B	0.0424	0.8159	0.3307	0.052*
C17	−0.03320 (8)	0.65957 (13)	0.33432 (8)	0.0392 (3)
O17A	−0.06599 (7)	0.87885 (11)	0.36661 (7)	0.0571 (3)
N17A	−0.09258 (8)	0.77231 (12)	0.33623 (7)	0.0465 (3)
O17D	−0.09839 (8)	0.60577 (14)	0.20439 (7)	0.0693 (4)
N17B	−0.08267 (7)	0.56468 (13)	0.27017 (7)	0.0500 (3)
O17C	−0.10468 (7)	0.45662 (12)	0.28897 (8)	0.0631 (3)
O17B	−0.16201 (7)	0.74303 (14)	0.31137 (8)	0.0697 (4)
C18	−0.01197 (8)	0.58382 (13)	0.41161 (8)	0.0404 (3)
H18A	−0.0597	0.5482	0.4186	0.049*
H18B	0.0214	0.5067	0.4100	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0380 (6)	0.0409 (6)	0.0370 (5)	−0.0005 (4)	0.0121 (5)	0.0018 (4)
O1	0.0742 (8)	0.0414 (6)	0.0569 (6)	0.0048 (5)	0.0202 (6)	0.0021 (5)
C1A	0.0373 (8)	0.0459 (8)	0.0474 (7)	0.0043 (6)	0.0119 (6)	−0.0019 (6)
C1B	0.0661 (11)	0.0583 (9)	0.0536 (9)	0.0043 (7)	0.0248 (8)	−0.0086 (7)
C2	0.0393 (8)	0.0474 (7)	0.0403 (7)	−0.0065 (6)	0.0133 (6)	0.0020 (5)
C3	0.0458 (8)	0.0429 (7)	0.0369 (6)	−0.0073 (6)	0.0103 (6)	0.0021 (5)
O3B	0.0578 (7)	0.0563 (6)	0.0354 (5)	−0.0103 (5)	0.0098 (4)	0.0021 (4)
O3A	0.0635 (7)	0.0454 (6)	0.0499 (6)	−0.0121 (5)	0.0186 (5)	0.0047 (4)
C3B	0.0607 (11)	0.0791 (11)	0.0433 (8)	−0.0100 (8)	0.0195 (7)	0.0055 (7)
C3A	0.0789 (13)	0.0665 (10)	0.0569 (9)	−0.0109 (9)	0.0220 (9)	0.0189 (8)
C4	0.0400 (8)	0.0562 (8)	0.0401 (7)	−0.0002 (6)	0.0069 (6)	0.0084 (6)
N5	0.0376 (6)	0.0437 (6)	0.0419 (6)	0.0033 (5)	0.0118 (5)	0.0059 (4)
O5	0.0990 (10)	0.0547 (6)	0.0493 (6)	0.0065 (6)	0.0206 (6)	−0.0028 (5)
C5A	0.0468 (9)	0.0450 (8)	0.0533 (8)	0.0082 (6)	0.0145 (7)	0.0011 (6)
C5B	0.0710 (12)	0.0441 (8)	0.0734 (11)	0.0041 (7)	0.0275 (9)	0.0030 (7)
C6	0.0358 (7)	0.0516 (8)	0.0441 (7)	−0.0018 (6)	0.0131 (6)	0.0052 (6)
C7	0.0432 (8)	0.0370 (7)	0.0378 (6)	−0.0038 (5)	0.0129 (6)	0.0008 (5)
O7C	0.0688 (8)	0.0760 (7)	0.0525 (6)	−0.0058 (6)	0.0329 (6)	0.0002 (5)
N7B	0.0522 (8)	0.0460 (6)	0.0396 (6)	0.0013 (5)	0.0151 (6)	0.0032 (5)
O7D	0.0531 (7)	0.0773 (8)	0.0443 (6)	−0.0022 (6)	0.0053 (5)	−0.0075 (5)
N7A	0.0605 (9)	0.0432 (7)	0.0576 (7)	−0.0086 (6)	0.0272 (7)	−0.0009 (6)
O7A	0.0959 (10)	0.0470 (6)	0.0699 (8)	0.0011 (6)	0.0287 (7)	0.0165 (5)
O7B	0.0644 (9)	0.0586 (7)	0.0986 (10)	−0.0231 (6)	0.0168 (8)	−0.0108 (7)
C8	0.0379 (7)	0.0408 (7)	0.0375 (6)	0.0004 (5)	0.0090 (5)	0.0027 (5)
N11	0.0485 (7)	0.0400 (6)	0.0404 (6)	0.0034 (5)	0.0168 (5)	0.0030 (4)
O11	0.0629 (8)	0.0605 (7)	0.0771 (8)	0.0086 (6)	0.0386 (6)	0.0041 (6)
C11B	0.0974 (15)	0.0648 (11)	0.0590 (10)	0.0101 (10)	0.0357 (10)	−0.0085 (8)
C11A	0.0660 (11)	0.0406 (7)	0.0494 (8)	0.0095 (7)	0.0273 (7)	0.0092 (6)
C12	0.0499 (9)	0.0430 (7)	0.0392 (7)	0.0057 (6)	0.0074 (6)	0.0008 (5)
C13	0.0371 (8)	0.0408 (7)	0.0466 (7)	0.0019 (5)	0.0028 (6)	−0.0054 (5)
O13A	0.0441 (6)	0.0394 (5)	0.0592 (6)	0.0030 (4)	0.0084 (5)	−0.0014 (4)
O13B	0.0450 (7)	0.0483 (6)	0.0660 (7)	0.0037 (5)	−0.0064 (5)	−0.0150 (5)
C13A	0.0583 (11)	0.0424 (8)	0.0919 (13)	−0.0030 (7)	0.0156 (9)	−0.0131 (8)
C13B	0.0628 (12)	0.0561 (10)	0.0796 (12)	−0.0007 (8)	−0.0007 (9)	−0.0283 (9)
C14	0.0385 (8)	0.0554 (8)	0.0579 (9)	−0.0096 (6)	0.0152 (7)	−0.0129 (7)
O15	0.0488 (7)	0.0691 (7)	0.0677 (7)	−0.0026 (5)	0.0081 (5)	−0.0308 (6)
N15	0.0368 (6)	0.0503 (7)	0.0434 (6)	−0.0050 (5)	0.0126 (5)	−0.0081 (5)
C15A	0.0439 (9)	0.0569 (9)	0.0483 (8)	−0.0019 (6)	0.0155 (7)	−0.0141 (6)
C15B	0.0520 (11)	0.0720 (11)	0.0791 (12)	0.0095 (8)	0.0095 (9)	−0.0253 (9)
C16	0.0411 (8)	0.0469 (7)	0.0410 (7)	−0.0039 (6)	0.0128 (6)	0.0035 (5)
C17	0.0359 (7)	0.0377 (7)	0.0423 (7)	−0.0005 (5)	0.0101 (5)	0.0001 (5)
O17A	0.0649 (7)	0.0398 (6)	0.0676 (7)	0.0053 (5)	0.0223 (6)	0.0024 (5)
N17A	0.0439 (8)	0.0436 (7)	0.0509 (7)	0.0053 (5)	0.0133 (5)	0.0083 (5)
O17D	0.0647 (8)	0.0844 (9)	0.0464 (6)	−0.0070 (6)	0.0002 (5)	−0.0037 (6)
N17B	0.0389 (7)	0.0533 (7)	0.0537 (7)	−0.0026 (5)	0.0088 (5)	−0.0066 (6)
O17C	0.0534 (7)	0.0505 (7)	0.0807 (8)	−0.0137 (5)	0.0146 (6)	−0.0086 (5)
O17B	0.0379 (7)	0.0726 (8)	0.0935 (9)	0.0065 (5)	0.0136 (6)	−0.0012 (7)
C18	0.0424 (8)	0.0340 (6)	0.0460 (7)	−0.0004 (5)	0.0156 (6)	0.0039 (5)

Geometric parameters (Å, º)

N1—C1A	1.3719 (18)	N11—C11A	1.3840 (19)
N1—C8	1.4661 (16)	N11—C18	1.4514 (18)
N1—C2	1.4683 (17)	N11—C12	1.458 (2)
O1—C1A	1.2240 (18)	O11—C11A	1.221 (2)
C1A—C1B	1.498 (2)	C11B—C11A	1.501 (2)
C2—C3	1.530 (2)	C12—C13	1.538 (2)
C3—O3B	1.4256 (16)	C13—O13A	1.4100 (17)
C3—O3A	1.4263 (17)	C13—O13B	1.4267 (18)
C3—C4	1.535 (2)	C13—C14	1.529 (2)
O3B—C3B	1.4257 (18)	O13A—C13A	1.435 (2)
O3A—C3A	1.4231 (19)	O13B—C13B	1.431 (2)
C3B—C3A	1.486 (3)	C13A—C13B	1.493 (3)
C4—N5	1.4620 (17)	C14—N15	1.4603 (18)
N5—C5A	1.366 (2)	O15—C15A	1.2239 (19)
N5—C6	1.4575 (18)	N15—C15A	1.360 (2)
O5—C5A	1.218 (2)	N15—C16	1.4550 (19)
C5A—C5B	1.501 (2)	C15A—C15B	1.498 (2)
C6—C7	1.5247 (19)	C16—C17	1.5302 (18)
C7—C8	1.5246 (18)	C17—C18	1.5334 (18)
C7—N7B	1.5425 (17)	C17—N17B	1.5385 (18)
C7—N7A	1.5497 (17)	C17—N17A	1.5424 (18)
O7C—N7B	1.2206 (16)	O17A—N17A	1.2067 (17)
N7B—O7D	1.2033 (17)	N17A—O17B	1.2179 (18)
N7A—O7B	1.2086 (19)	O17D—N17B	1.2137 (18)
N7A—O7A	1.2175 (19)	N17B—O17C	1.2164 (18)
C1A—N1—C8	116.44 (11)	C11A—N11—C18	115.68 (13)
C1A—N1—C2	123.30 (11)	C11A—N11—C12	123.08 (12)
C8—N1—C2	116.77 (10)	C18—N11—C12	119.64 (11)
O1—C1A—N1	119.61 (13)	O11—C11A—N11	120.06 (15)
O1—C1A—C1B	121.12 (13)	O11—C11A—C11B	121.67 (15)
N1—C1A—C1B	119.26 (13)	N11—C11A—C11B	118.27 (16)
N1—C2—C3	117.13 (11)	N11—C12—C13	116.90 (11)
O3B—C3—O3A	106.02 (10)	O13A—C13—O13B	107.27 (11)
O3B—C3—C2	113.19 (12)	O13A—C13—C14	112.05 (12)
O3A—C3—C2	104.52 (11)	O13B—C13—C14	105.82 (12)
O3B—C3—C4	105.29 (11)	O13A—C13—C12	108.77 (12)
O3A—C3—C4	112.15 (12)	O13B—C13—C12	108.02 (12)
C2—C3—C4	115.44 (11)	C14—C13—C12	114.56 (12)
C3B—O3B—C3	106.84 (11)	C13—O13A—C13A	106.41 (11)
C3A—O3A—C3	107.95 (12)	C13—O13B—C13B	107.42 (12)
O3B—C3B—C3A	101.91 (13)	O13A—C13A—C13B	101.99 (14)
O3A—C3A—C3B	103.13 (13)	O13B—C13B—C13A	103.00 (13)
N5—C4—C3	115.41 (12)	N15—C14—C13	114.03 (12)
C5A—N5—C6	116.62 (11)	C15A—N15—C16	117.75 (12)
C5A—N5—C4	124.96 (12)	C15A—N15—C14	124.40 (13)
C6—N5—C4	116.92 (11)	C16—N15—C14	117.52 (12)
O5—C5A—N5	119.34 (14)	O15—C15A—N15	118.88 (14)
O5—C5A—C5B	121.12 (15)	O15—C15A—C15B	121.25 (15)
N5—C5A—C5B	119.54 (13)	N15—C15A—C15B	119.84 (14)
N5—C6—C7	114.23 (11)	N15—C16—C17	112.96 (11)
C6—C7—C8	115.86 (11)	C16—C17—C18	115.43 (11)
C6—C7—N7B	110.68 (11)	C16—C17—N17B	111.79 (11)
C8—C7—N7B	109.29 (11)	C18—C17—N17B	109.00 (11)
C6—C7—N7A	109.38 (11)	C16—C17—N17A	110.15 (10)
C8—C7—N7A	110.71 (11)	C18—C17—N17A	107.25 (10)
N7B—C7—N7A	99.74 (10)	N17B—C17—N17A	102.32 (10)
O7D—N7B—O7C	125.46 (12)	O17A—N17A—O17B	125.71 (13)
O7D—N7B—C7	118.73 (11)	O17A—N17A—C17	116.97 (12)
O7C—N7B—C7	115.79 (12)	O17B—N17A—C17	117.14 (12)
O7B—N7A—O7A	125.44 (14)	O17D—N17B—O17C	125.04 (14)
O7B—N7A—C7	118.49 (13)	O17D—N17B—C17	116.88 (13)
O7A—N7A—C7	116.07 (13)	O17C—N17B—C17	118.04 (12)
N1—C8—C7	114.51 (11)	N11—C18—C17	113.42 (11)