(E)-9,10-Dihydro-9-methyl-9-nitro-10-(trinitro­meth­yl)anthracene

The title compound, C₁₆H₁₂N₄O₈, was prepared by the photochemical reaction of 9-methyl­anthracene and tetra­nitro­methane in dichloromethane. Intermolecula face-to-face π–π stacking inter­actions are present along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.133
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O9A    ..  N1      ..       2.87 Ang.

Alert level C
PLAT430_ALERT_2_C Short Inter D...A Contact  O1A    ..  O9A     ..       2.89 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4-PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4-PC Software; data reduction: DATRD2 in NRCVAX (Gabe et al., 1989); 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) and PLATON/PLUTON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

E)-9,10-Dihydro-9-methyl-9-nitro-10-(trinitromethyl)anthracene

Crystal data

C16H12N4O8	F(000) = 800
Mr = 388.3	Dx = 1.552 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 7.9797 (6) Å	θ = 20–25°
b = 13.5449 (10) Å	µ = 0.13 mm^−1
c = 15.3793 (9) Å	T = 295 K
β = 91.816 (6)°	Plate, colorless
V = 1661.4 (2) Å^3	0.35 × 0.35 × 0.18 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 2°
Graphite monochromator	h = −9→9
ω scans	k = 0→16
2949 measured reflections	l = 0→18
2949 independent reflections	3 standard reflections every 120 min
2311 reflections with I > 2σ(I)	intensity decay: 1.1%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.1197P)^2 + 9.7917P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.133	(Δ/σ)max = 0.015
S = 1.06	Δρmax = 0.21 e Å^−3
2949 reflections	Δρmin = −0.15 e Å^−3
253 parameters

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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

4.7343 (0.0054) x + 6.0935 (0.0107) y + 9.9722 (0.0102) z = 7.7588 (0.0014)

* -0.0020 (0.0015) C1 * -0.0111 (0.0017) C2 * 0.0111 (0.0016) C3 * 0.0022 (0.0013) C4 * -0.0152 (0.0012) C4A * 0.0150 (0.0013) C9A

Rms deviation of fitted atoms = 0.0109

7.0843 (0.0030) x + 1.5222 (0.0104) y + 6.4279 (0.0112) z = 5.7333 (0.0063)

Angle to previous plane (with approximate e.s.d.) = 28.93 (0.09)

* -0.0009 (0.0013) C5 * 0.0052 (0.0014) C6 * -0.0007 (0.0015) C7 * -0.0080 (0.0014) C8 * 0.0121 (0.0012) C8A * -0.0077 (0.0012) C10A

Rms deviation of fitted atoms = 0.0070

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
O1A	0.2306 (3)	0.20042 (13)	0.25567 (13)	0.0576 (5)
N3	0.1289 (3)	0.40009 (16)	0.27366 (13)	0.0421 (5)
C10A	0.3382 (3)	0.41477 (16)	0.41967 (14)	0.0334 (5)
O3B	0.0381 (2)	0.34284 (16)	0.30814 (14)	0.0629 (6)
N1	0.3083 (3)	0.26245 (16)	0.21832 (13)	0.0425 (5)
C4A	0.5177 (3)	0.27928 (16)	0.36004 (14)	0.0326 (5)
C8A	0.2930 (3)	0.35342 (17)	0.48729 (14)	0.0345 (5)
N9	0.3942 (3)	0.21578 (16)	0.57756 (13)	0.0485 (5)
O9A	0.5190 (3)	0.25872 (17)	0.60388 (13)	0.0709 (6)
N2	0.3625 (3)	0.43354 (18)	0.18191 (14)	0.0537 (6)
C9A	0.4681 (3)	0.21582 (16)	0.42544 (14)	0.0353 (5)
C10	0.4253 (3)	0.37449 (16)	0.34125 (13)	0.0316 (5)
H10	0.5116	0.4231	0.3276	0.038*
O1B	0.3976 (3)	0.25003 (18)	0.15779 (14)	0.0727 (6)
C12	0.3076 (3)	0.36670 (16)	0.25680 (14)	0.0342 (5)
O2B	0.2733 (3)	0.43189 (19)	0.11673 (13)	0.0813 (8)
C5	0.3122 (3)	0.51624 (17)	0.42564 (17)	0.0430 (6)
H5	0.3445	0.5572	0.3807	0.052*
O3A	0.0981 (3)	0.48531 (16)	0.25704 (16)	0.0752 (7)
C9	0.3259 (3)	0.24303 (17)	0.48427 (14)	0.0366 (5)
C8	0.2163 (3)	0.3949 (2)	0.55873 (16)	0.0469 (6)
H8	0.1817	0.3544	0.6035	0.056*
C6	0.2391 (3)	0.5564 (2)	0.49727 (18)	0.0520 (7)
H6	0.2222	0.6242	0.5008	0.062*
O2A	0.4875 (3)	0.4822 (2)	0.19315 (15)	0.0870 (8)
C4	0.6557 (3)	0.25506 (19)	0.31115 (16)	0.0437 (6)
H4	0.691	0.2984	0.2686	0.052*
O9B	0.3221 (3)	0.15310 (17)	0.61850 (14)	0.0790 (7)
C3	0.7405 (3)	0.1679 (2)	0.32506 (19)	0.0571 (7)
H3	0.8332	0.1528	0.2924	0.069*
C1	0.5538 (4)	0.12737 (19)	0.43706 (18)	0.0529 (7)
H1	0.5197	0.0835	0.4795	0.064*
C11	0.1666 (3)	0.1836 (2)	0.46620 (17)	0.0506 (6)
H15A	0.0822	0.2037	0.5056	0.076*
H15B	0.1901	0.1146	0.4742	0.076*
H15C	0.1272	0.1949	0.4074	0.076*
C7	0.1912 (3)	0.4955 (2)	0.56380 (19)	0.0560 (7)
H7	0.1417	0.5223	0.6124	0.067*
C2	0.6880 (4)	0.1031 (2)	0.3872 (2)	0.0615 (8)
H2	0.7429	0.0431	0.3957	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0773 (13)	0.0367 (10)	0.0581 (11)	−0.0099 (9)	−0.0121 (10)	0.0015 (9)
N3	0.0416 (11)	0.0484 (12)	0.0356 (10)	0.0038 (10)	−0.0095 (9)	−0.0039 (9)
C10A	0.0317 (11)	0.0345 (12)	0.0337 (11)	−0.0014 (9)	−0.0065 (9)	−0.0044 (9)
O3B	0.0471 (11)	0.0713 (14)	0.0709 (13)	−0.0086 (10)	0.0146 (10)	−0.0018 (11)
N1	0.0455 (11)	0.0453 (12)	0.0361 (11)	0.0030 (9)	−0.0087 (9)	−0.0072 (9)
C4A	0.0307 (10)	0.0355 (11)	0.0312 (11)	−0.0004 (9)	−0.0042 (8)	−0.0025 (9)
C8A	0.0320 (11)	0.0391 (12)	0.0322 (11)	−0.0024 (9)	−0.0027 (9)	−0.0044 (9)
N9	0.0667 (14)	0.0449 (12)	0.0336 (11)	0.0001 (11)	−0.0036 (10)	0.0039 (9)
O9A	0.0789 (14)	0.0756 (14)	0.0559 (12)	−0.0104 (12)	−0.0325 (11)	0.0047 (11)
N2	0.0606 (14)	0.0584 (14)	0.0418 (12)	−0.0147 (12)	−0.0011 (11)	0.0144 (10)
C9A	0.0386 (12)	0.0338 (11)	0.0333 (11)	−0.0011 (9)	−0.0043 (9)	−0.0019 (9)
C10	0.0328 (11)	0.0302 (11)	0.0315 (11)	−0.0057 (9)	−0.0029 (9)	0.0025 (9)
O1B	0.0741 (14)	0.0877 (16)	0.0569 (12)	0.0083 (12)	0.0134 (11)	−0.0279 (11)
C12	0.0383 (11)	0.0349 (12)	0.0295 (11)	−0.0028 (9)	0.0010 (9)	0.0026 (9)
O2B	0.1028 (18)	0.0961 (18)	0.0435 (11)	−0.0274 (14)	−0.0223 (12)	0.0270 (11)
C5	0.0466 (13)	0.0332 (12)	0.0484 (14)	−0.0002 (10)	−0.0109 (11)	−0.0036 (10)
O3A	0.0745 (15)	0.0549 (13)	0.0954 (17)	0.0251 (11)	−0.0115 (13)	0.0093 (12)
C9	0.0441 (12)	0.0368 (12)	0.0287 (11)	−0.0047 (10)	−0.0022 (9)	0.0028 (9)
C8	0.0420 (13)	0.0604 (16)	0.0385 (13)	0.0023 (12)	0.0051 (10)	−0.0075 (12)
C6	0.0532 (15)	0.0429 (14)	0.0592 (17)	0.0110 (12)	−0.0110 (13)	−0.0176 (13)
O2A	0.0865 (16)	0.1066 (19)	0.0674 (14)	−0.0510 (15)	−0.0079 (12)	0.0369 (13)
C4	0.0359 (12)	0.0511 (14)	0.0443 (13)	0.0017 (11)	0.0021 (10)	−0.0020 (11)
O9B	0.1157 (19)	0.0744 (15)	0.0468 (11)	−0.0154 (14)	0.0020 (12)	0.0231 (11)
C3	0.0437 (14)	0.0665 (18)	0.0613 (17)	0.0150 (13)	0.0044 (13)	−0.0118 (15)
C1	0.0656 (17)	0.0385 (14)	0.0544 (16)	0.0063 (12)	−0.0015 (13)	0.0062 (12)
C11	0.0546 (15)	0.0506 (15)	0.0467 (14)	−0.0166 (12)	0.0021 (12)	−0.0014 (12)
C7	0.0446 (14)	0.0694 (19)	0.0542 (16)	0.0120 (13)	0.0027 (12)	−0.0270 (15)
C2	0.0628 (18)	0.0475 (16)	0.074 (2)	0.0222 (14)	0.0009 (15)	−0.0041 (15)

Geometric parameters (Å, º)

O1A—N1	1.201 (3)	C9A—C9	1.518 (3)
N3—O3B	1.197 (3)	C10—C12	1.582 (3)
N3—O3A	1.206 (3)	C10—H10	0.98
N3—C12	1.526 (3)	C5—C6	1.375 (4)
C10A—C8A	1.388 (3)	C5—H5	0.93
C10A—C5	1.394 (3)	C9—C11	1.523 (3)
C10A—C10	1.513 (3)	C8—C7	1.379 (4)
N1—O1B	1.202 (3)	C8—H8	0.93
N1—C12	1.531 (3)	C6—C7	1.378 (4)
C4A—C4	1.392 (3)	C6—H6	0.93
C4A—C9A	1.390 (3)	C4—C3	1.375 (4)
C4A—C10	1.509 (3)	C4—H4	0.93
C8A—C8	1.393 (3)	C3—C2	1.373 (4)
C8A—C9	1.519 (3)	C3—H3	0.93
N9—O9A	1.212 (3)	C1—C2	1.376 (4)
N9—O9B	1.213 (3)	C1—H1	0.93
N9—C9	1.563 (3)	C11—H15A	0.96
N2—O2A	1.203 (3)	C11—H15B	0.96
N2—O2B	1.211 (3)	C11—H15C	0.96
N2—C12	1.540 (3)	C7—H7	0.93
C9A—C1	1.388 (3)	C2—H2	0.93
O3B—N3—O3A	126.3 (2)	C6—C5—C10A	120.7 (2)
O3B—N3—C12	117.7 (2)	C6—C5—H5	119.6
O3A—N3—C12	115.7 (2)	C10A—C5—H5	119.6
C8A—C10A—C5	119.9 (2)	C9A—C9—C11	113.44 (19)
C8A—C10A—C10	121.2 (2)	C9A—C9—C8A	112.98 (18)
C5—C10A—C10	118.8 (2)	C11—C9—C8A	112.5 (2)
O1A—N1—O1B	126.9 (2)	C9A—C9—N9	104.15 (18)
O1A—N1—C12	116.88 (19)	C11—C9—N9	107.89 (19)
O1B—N1—C12	116.0 (2)	C8A—C9—N9	105.07 (18)
C4—C4A—C9A	119.6 (2)	C7—C8—C8A	120.8 (3)
C4—C4A—C10	119.2 (2)	C7—C8—H8	119.6
C9A—C4A—C10	121.21 (19)	C8A—C8—H8	119.6
C8—C8A—C10A	118.7 (2)	C5—C6—C7	119.5 (2)
C8—C8A—C9	120.2 (2)	C5—C6—H6	120.2
C10A—C8A—C9	121.1 (2)	C7—C6—H6	120.2
O9A—N9—O9B	124.1 (2)	C3—C4—C4A	120.8 (2)
O9A—N9—C9	116.9 (2)	C3—C4—H4	119.6
O9B—N9—C9	119.0 (2)	C4A—C4—H4	119.6
O2A—N2—O2B	126.3 (2)	C4—C3—C2	119.9 (3)
O2A—N2—C12	118.0 (2)	C4—C3—H3	120.1
O2B—N2—C12	115.7 (2)	C2—C3—H3	120.1
C1—C9A—C4A	118.4 (2)	C2—C1—C9A	121.6 (3)
C1—C9A—C9	120.5 (2)	C2—C1—H1	119.2
C4A—C9A—C9	121.1 (2)	C9A—C1—H1	119.2
C10A—C10—C4A	112.93 (17)	C9—C11—H15A	109.5
C10A—C10—C12	113.77 (17)	C9—C11—H15B	109.5
C4A—C10—C12	111.97 (17)	H15A—C11—H15B	109.5
C10A—C10—H10	105.8	C9—C11—H15C	109.5
C4A—C10—H10	105.8	H15A—C11—H15C	109.5
C12—C10—H10	105.8	H15B—C11—H15C	109.5
N3—C12—N2	104.05 (18)	C6—C7—C8	120.4 (2)
N3—C12—N1	110.72 (17)	C6—C7—H7	119.8
N2—C12—N1	104.40 (18)	C8—C7—H7	119.8
N3—C12—C10	111.98 (17)	C3—C2—C1	119.7 (3)
N2—C12—C10	113.53 (18)	C3—C2—H2	120.2
N1—C12—C10	111.69 (17)	C1—C2—H2	120.2
C5—C10A—C8A—C8	2.3 (3)	C10A—C10—C12—N2	116.3 (2)
C10—C10A—C8A—C8	178.6 (2)	C4A—C10—C12—N2	−114.1 (2)
C5—C10A—C8A—C9	−177.6 (2)	C10A—C10—C12—N1	−125.95 (19)
C10—C10A—C8A—C9	−1.3 (3)	C4A—C10—C12—N1	3.6 (2)
C4—C4A—C9A—C1	−3.1 (3)	C8A—C10A—C5—C6	−1.2 (3)
C10—C4A—C9A—C1	177.3 (2)	C10—C10A—C5—C6	−177.6 (2)
C4—C4A—C9A—C9	175.7 (2)	C1—C9A—C9—C11	−73.1 (3)
C10—C4A—C9A—C9	−4.0 (3)	C4A—C9A—C9—C11	108.2 (2)
C8A—C10A—C10—C4A	−23.9 (3)	C1—C9A—C9—C8A	157.4 (2)
C5—C10A—C10—C4A	152.5 (2)	C4A—C9A—C9—C8A	−21.3 (3)
C8A—C10A—C10—C12	105.2 (2)	C1—C9A—C9—N9	43.9 (3)
C5—C10A—C10—C12	−78.5 (2)	C4A—C9A—C9—N9	−134.8 (2)
C4—C4A—C10—C10A	−153.1 (2)	C8—C8A—C9—C9A	−155.9 (2)
C9A—C4A—C10—C10A	26.6 (3)	C10A—C8A—C9—C9A	24.0 (3)
C4—C4A—C10—C12	77.0 (2)	C8—C8A—C9—C11	74.1 (3)
C9A—C4A—C10—C12	−103.4 (2)	C10A—C8A—C9—C11	−106.0 (2)
O3B—N3—C12—N2	157.0 (2)	C8—C8A—C9—N9	−43.0 (3)
O3A—N3—C12—N2	−28.9 (3)	C10A—C8A—C9—N9	136.9 (2)
O3B—N3—C12—N1	45.4 (3)	O9A—N9—C9—C9A	61.2 (3)
O3A—N3—C12—N1	−140.5 (2)	O9B—N9—C9—C9A	−117.9 (2)
O3B—N3—C12—C10	−80.0 (2)	O9A—N9—C9—C11	−178.0 (2)
O3A—N3—C12—C10	94.1 (2)	O9B—N9—C9—C11	3.0 (3)
O2A—N2—C12—N3	123.6 (3)	O9A—N9—C9—C8A	−57.8 (3)
O2B—N2—C12—N3	−56.1 (3)	O9B—N9—C9—C8A	123.1 (2)
O2A—N2—C12—N1	−120.2 (3)	C10A—C8A—C8—C7	−2.3 (4)
O2B—N2—C12—N1	60.0 (3)	C9—C8A—C8—C7	177.6 (2)
O2A—N2—C12—C10	1.6 (3)	C10A—C5—C6—C7	0.0 (4)
O2B—N2—C12—C10	−178.1 (2)	C9A—C4A—C4—C3	1.9 (3)
O1A—N1—C12—N3	−50.3 (2)	C10—C4A—C4—C3	−178.4 (2)
O1B—N1—C12—N3	135.4 (2)	C4A—C4—C3—C2	0.7 (4)
O1A—N1—C12—N2	−161.7 (2)	C4A—C9A—C1—C2	1.8 (4)
O1B—N1—C12—N2	24.0 (3)	C9—C9A—C1—C2	−177.0 (2)
O1A—N1—C12—C10	75.2 (2)	C5—C6—C7—C8	0.1 (4)
O1B—N1—C12—C10	−99.1 (2)	C8A—C8—C7—C6	1.1 (4)
C10A—C10—C12—N3	−1.1 (3)	C4—C3—C2—C1	−2.0 (5)
C4A—C10—C12—N3	128.42 (19)	C9A—C1—C2—C3	0.7 (5)