Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805036974/ac6219sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805036974/ac6219Isup2.hkl
Contains datablock I

CCDC reference: 293809

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

Computing details top

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 top
Crystal data top
C16H12N4O8F(000) = 800
Mr = 388.3Dx = 1.552 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 7.9797 (6) Åθ = 20–25°
b = 13.5449 (10) ŵ = 0.13 mm1
c = 15.3793 (9) ÅT = 295 K
β = 91.816 (6)°Plate, colorless
V = 1661.4 (2) Å30.35 × 0.35 × 0.18 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 2°
Graphite monochromatorh = 99
ω scansk = 016
2949 measured reflectionsl = 018
2949 independent reflections3 standard reflections every 120 min
2311 reflections with I > 2σ(I) intensity decay: 1.1%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.1197P)2 + 9.7917P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.133(Δ/σ)max = 0.015
S = 1.06Δρmax = 0.21 e Å3
2949 reflectionsΔρmin = 0.15 e Å3
253 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
O1A0.2306 (3)0.20042 (13)0.25567 (13)0.0576 (5)
N30.1289 (3)0.40009 (16)0.27366 (13)0.0421 (5)
C10A0.3382 (3)0.41477 (16)0.41967 (14)0.0334 (5)
O3B0.0381 (2)0.34284 (16)0.30814 (14)0.0629 (6)
N10.3083 (3)0.26245 (16)0.21832 (13)0.0425 (5)
C4A0.5177 (3)0.27928 (16)0.36004 (14)0.0326 (5)
C8A0.2930 (3)0.35342 (17)0.48729 (14)0.0345 (5)
N90.3942 (3)0.21578 (16)0.57756 (13)0.0485 (5)
O9A0.5190 (3)0.25872 (17)0.60388 (13)0.0709 (6)
N20.3625 (3)0.43354 (18)0.18191 (14)0.0537 (6)
C9A0.4681 (3)0.21582 (16)0.42544 (14)0.0353 (5)
C100.4253 (3)0.37449 (16)0.34125 (13)0.0316 (5)
H100.51160.42310.32760.038*
O1B0.3976 (3)0.25003 (18)0.15779 (14)0.0727 (6)
C120.3076 (3)0.36670 (16)0.25680 (14)0.0342 (5)
O2B0.2733 (3)0.43189 (19)0.11673 (13)0.0813 (8)
C50.3122 (3)0.51624 (17)0.42564 (17)0.0430 (6)
H50.34450.55720.38070.052*
O3A0.0981 (3)0.48531 (16)0.25704 (16)0.0752 (7)
C90.3259 (3)0.24303 (17)0.48427 (14)0.0366 (5)
C80.2163 (3)0.3949 (2)0.55873 (16)0.0469 (6)
H80.18170.35440.60350.056*
C60.2391 (3)0.5564 (2)0.49727 (18)0.0520 (7)
H60.22220.62420.50080.062*
O2A0.4875 (3)0.4822 (2)0.19315 (15)0.0870 (8)
C40.6557 (3)0.25506 (19)0.31115 (16)0.0437 (6)
H40.6910.29840.26860.052*
O9B0.3221 (3)0.15310 (17)0.61850 (14)0.0790 (7)
C30.7405 (3)0.1679 (2)0.32506 (19)0.0571 (7)
H30.83320.15280.29240.069*
C10.5538 (4)0.12737 (19)0.43706 (18)0.0529 (7)
H10.51970.08350.47950.064*
C110.1666 (3)0.1836 (2)0.46620 (17)0.0506 (6)
H15A0.08220.20370.50560.076*
H15B0.19010.11460.47420.076*
H15C0.12720.19490.40740.076*
C70.1912 (3)0.4955 (2)0.56380 (19)0.0560 (7)
H70.14170.52230.61240.067*
C20.6880 (4)0.1031 (2)0.3872 (2)0.0615 (8)
H20.74290.04310.39570.074*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0773 (13)0.0367 (10)0.0581 (11)0.0099 (9)0.0121 (10)0.0015 (9)
N30.0416 (11)0.0484 (12)0.0356 (10)0.0038 (10)0.0095 (9)0.0039 (9)
C10A0.0317 (11)0.0345 (12)0.0337 (11)0.0014 (9)0.0065 (9)0.0044 (9)
O3B0.0471 (11)0.0713 (14)0.0709 (13)0.0086 (10)0.0146 (10)0.0018 (11)
N10.0455 (11)0.0453 (12)0.0361 (11)0.0030 (9)0.0087 (9)0.0072 (9)
C4A0.0307 (10)0.0355 (11)0.0312 (11)0.0004 (9)0.0042 (8)0.0025 (9)
C8A0.0320 (11)0.0391 (12)0.0322 (11)0.0024 (9)0.0027 (9)0.0044 (9)
N90.0667 (14)0.0449 (12)0.0336 (11)0.0001 (11)0.0036 (10)0.0039 (9)
O9A0.0789 (14)0.0756 (14)0.0559 (12)0.0104 (12)0.0325 (11)0.0047 (11)
N20.0606 (14)0.0584 (14)0.0418 (12)0.0147 (12)0.0011 (11)0.0144 (10)
C9A0.0386 (12)0.0338 (11)0.0333 (11)0.0011 (9)0.0043 (9)0.0019 (9)
C100.0328 (11)0.0302 (11)0.0315 (11)0.0057 (9)0.0029 (9)0.0025 (9)
O1B0.0741 (14)0.0877 (16)0.0569 (12)0.0083 (12)0.0134 (11)0.0279 (11)
C120.0383 (11)0.0349 (12)0.0295 (11)0.0028 (9)0.0010 (9)0.0026 (9)
O2B0.1028 (18)0.0961 (18)0.0435 (11)0.0274 (14)0.0223 (12)0.0270 (11)
C50.0466 (13)0.0332 (12)0.0484 (14)0.0002 (10)0.0109 (11)0.0036 (10)
O3A0.0745 (15)0.0549 (13)0.0954 (17)0.0251 (11)0.0115 (13)0.0093 (12)
C90.0441 (12)0.0368 (12)0.0287 (11)0.0047 (10)0.0022 (9)0.0028 (9)
C80.0420 (13)0.0604 (16)0.0385 (13)0.0023 (12)0.0051 (10)0.0075 (12)
C60.0532 (15)0.0429 (14)0.0592 (17)0.0110 (12)0.0110 (13)0.0176 (13)
O2A0.0865 (16)0.1066 (19)0.0674 (14)0.0510 (15)0.0079 (12)0.0369 (13)
C40.0359 (12)0.0511 (14)0.0443 (13)0.0017 (11)0.0021 (10)0.0020 (11)
O9B0.1157 (19)0.0744 (15)0.0468 (11)0.0154 (14)0.0020 (12)0.0231 (11)
C30.0437 (14)0.0665 (18)0.0613 (17)0.0150 (13)0.0044 (13)0.0118 (15)
C10.0656 (17)0.0385 (14)0.0544 (16)0.0063 (12)0.0015 (13)0.0062 (12)
C110.0546 (15)0.0506 (15)0.0467 (14)0.0166 (12)0.0021 (12)0.0014 (12)
C70.0446 (14)0.0694 (19)0.0542 (16)0.0120 (13)0.0027 (12)0.0270 (15)
C20.0628 (18)0.0475 (16)0.074 (2)0.0222 (14)0.0009 (15)0.0041 (15)
Geometric parameters (Å, º) top
O1A—N11.201 (3)C9A—C91.518 (3)
N3—O3B1.197 (3)C10—C121.582 (3)
N3—O3A1.206 (3)C10—H100.98
N3—C121.526 (3)C5—C61.375 (4)
C10A—C8A1.388 (3)C5—H50.93
C10A—C51.394 (3)C9—C111.523 (3)
C10A—C101.513 (3)C8—C71.379 (4)
N1—O1B1.202 (3)C8—H80.93
N1—C121.531 (3)C6—C71.378 (4)
C4A—C41.392 (3)C6—H60.93
C4A—C9A1.390 (3)C4—C31.375 (4)
C4A—C101.509 (3)C4—H40.93
C8A—C81.393 (3)C3—C21.373 (4)
C8A—C91.519 (3)C3—H30.93
N9—O9A1.212 (3)C1—C21.376 (4)
N9—O9B1.213 (3)C1—H10.93
N9—C91.563 (3)C11—H15A0.96
N2—O2A1.203 (3)C11—H15B0.96
N2—O2B1.211 (3)C11—H15C0.96
N2—C121.540 (3)C7—H70.93
C9A—C11.388 (3)C2—H20.93
O3B—N3—O3A126.3 (2)C6—C5—C10A120.7 (2)
O3B—N3—C12117.7 (2)C6—C5—H5119.6
O3A—N3—C12115.7 (2)C10A—C5—H5119.6
C8A—C10A—C5119.9 (2)C9A—C9—C11113.44 (19)
C8A—C10A—C10121.2 (2)C9A—C9—C8A112.98 (18)
C5—C10A—C10118.8 (2)C11—C9—C8A112.5 (2)
O1A—N1—O1B126.9 (2)C9A—C9—N9104.15 (18)
O1A—N1—C12116.88 (19)C11—C9—N9107.89 (19)
O1B—N1—C12116.0 (2)C8A—C9—N9105.07 (18)
C4—C4A—C9A119.6 (2)C7—C8—C8A120.8 (3)
C4—C4A—C10119.2 (2)C7—C8—H8119.6
C9A—C4A—C10121.21 (19)C8A—C8—H8119.6
C8—C8A—C10A118.7 (2)C5—C6—C7119.5 (2)
C8—C8A—C9120.2 (2)C5—C6—H6120.2
C10A—C8A—C9121.1 (2)C7—C6—H6120.2
O9A—N9—O9B124.1 (2)C3—C4—C4A120.8 (2)
O9A—N9—C9116.9 (2)C3—C4—H4119.6
O9B—N9—C9119.0 (2)C4A—C4—H4119.6
O2A—N2—O2B126.3 (2)C4—C3—C2119.9 (3)
O2A—N2—C12118.0 (2)C4—C3—H3120.1
O2B—N2—C12115.7 (2)C2—C3—H3120.1
C1—C9A—C4A118.4 (2)C2—C1—C9A121.6 (3)
C1—C9A—C9120.5 (2)C2—C1—H1119.2
C4A—C9A—C9121.1 (2)C9A—C1—H1119.2
C10A—C10—C4A112.93 (17)C9—C11—H15A109.5
C10A—C10—C12113.77 (17)C9—C11—H15B109.5
C4A—C10—C12111.97 (17)H15A—C11—H15B109.5
C10A—C10—H10105.8C9—C11—H15C109.5
C4A—C10—H10105.8H15A—C11—H15C109.5
C12—C10—H10105.8H15B—C11—H15C109.5
N3—C12—N2104.05 (18)C6—C7—C8120.4 (2)
N3—C12—N1110.72 (17)C6—C7—H7119.8
N2—C12—N1104.40 (18)C8—C7—H7119.8
N3—C12—C10111.98 (17)C3—C2—C1119.7 (3)
N2—C12—C10113.53 (18)C3—C2—H2120.2
N1—C12—C10111.69 (17)C1—C2—H2120.2
C5—C10A—C8A—C82.3 (3)C10A—C10—C12—N2116.3 (2)
C10—C10A—C8A—C8178.6 (2)C4A—C10—C12—N2114.1 (2)
C5—C10A—C8A—C9177.6 (2)C10A—C10—C12—N1125.95 (19)
C10—C10A—C8A—C91.3 (3)C4A—C10—C12—N13.6 (2)
C4—C4A—C9A—C13.1 (3)C8A—C10A—C5—C61.2 (3)
C10—C4A—C9A—C1177.3 (2)C10—C10A—C5—C6177.6 (2)
C4—C4A—C9A—C9175.7 (2)C1—C9A—C9—C1173.1 (3)
C10—C4A—C9A—C94.0 (3)C4A—C9A—C9—C11108.2 (2)
C8A—C10A—C10—C4A23.9 (3)C1—C9A—C9—C8A157.4 (2)
C5—C10A—C10—C4A152.5 (2)C4A—C9A—C9—C8A21.3 (3)
C8A—C10A—C10—C12105.2 (2)C1—C9A—C9—N943.9 (3)
C5—C10A—C10—C1278.5 (2)C4A—C9A—C9—N9134.8 (2)
C4—C4A—C10—C10A153.1 (2)C8—C8A—C9—C9A155.9 (2)
C9A—C4A—C10—C10A26.6 (3)C10A—C8A—C9—C9A24.0 (3)
C4—C4A—C10—C1277.0 (2)C8—C8A—C9—C1174.1 (3)
C9A—C4A—C10—C12103.4 (2)C10A—C8A—C9—C11106.0 (2)
O3B—N3—C12—N2157.0 (2)C8—C8A—C9—N943.0 (3)
O3A—N3—C12—N228.9 (3)C10A—C8A—C9—N9136.9 (2)
O3B—N3—C12—N145.4 (3)O9A—N9—C9—C9A61.2 (3)
O3A—N3—C12—N1140.5 (2)O9B—N9—C9—C9A117.9 (2)
O3B—N3—C12—C1080.0 (2)O9A—N9—C9—C11178.0 (2)
O3A—N3—C12—C1094.1 (2)O9B—N9—C9—C113.0 (3)
O2A—N2—C12—N3123.6 (3)O9A—N9—C9—C8A57.8 (3)
O2B—N2—C12—N356.1 (3)O9B—N9—C9—C8A123.1 (2)
O2A—N2—C12—N1120.2 (3)C10A—C8A—C8—C72.3 (4)
O2B—N2—C12—N160.0 (3)C9—C8A—C8—C7177.6 (2)
O2A—N2—C12—C101.6 (3)C10A—C5—C6—C70.0 (4)
O2B—N2—C12—C10178.1 (2)C9A—C4A—C4—C31.9 (3)
O1A—N1—C12—N350.3 (2)C10—C4A—C4—C3178.4 (2)
O1B—N1—C12—N3135.4 (2)C4A—C4—C3—C20.7 (4)
O1A—N1—C12—N2161.7 (2)C4A—C9A—C1—C21.8 (4)
O1B—N1—C12—N224.0 (3)C9—C9A—C1—C2177.0 (2)
O1A—N1—C12—C1075.2 (2)C5—C6—C7—C80.1 (4)
O1B—N1—C12—C1099.1 (2)C8A—C8—C7—C61.1 (4)
C10A—C10—C12—N31.1 (3)C4—C3—C2—C12.0 (5)
C4A—C10—C12—N3128.42 (19)C9A—C1—C2—C30.7 (5)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds