Download citation
Download citation
link to html
The structure of 1,3,4-tri­nitro-7,8-di­aza­pentalene, C6H3N5O6, is reported. In this mol­ecule, while the 7,8-di­aza­pentalene skeleton is planar, the nitro groups are twisted with respect to and deviate from this plane. The metrical parameters of the monosubstituted and disubstituted five-membered rings differ.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803020051/cv6220sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803020051/cv6220Isup2.hkl
Contains datablock I

CCDC reference: 227006

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.048
  • wR factor = 0.110
  • Data-to-parameter ratio = 5.5

checkCIF/PLATON results

No syntax errors found




Alert level A ABSTM02_ALERT_3_A The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 Tmin and Tmax reported: 0.190 0.981 Tmin' and Tmax expected: 0.943 0.979 RR' = 0.201 Please check that your absorption correction is appropriate. DENSX01_ALERT_1_A The ratio of the calculated to measured crystal density lies outside the range 0.80 <> 1.20 Calculated density = 1.829 Measured density = 0.000 PLAT061_ALERT_3_A Tmax/Tmin Range Test RR' too Large ............. 0.20
Alert level B REFNR01_ALERT_3_B Ratio of reflections to parameters is < 6 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.3033 Proportion of unique data used 1.0000 Ratio reflections to parameters 5.4903 PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.50 Sigma PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 5.49 PLAT430_ALERT_2_B Short Inter D...A Contact O41 .. N8 = 2.80 Ang.
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.102 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT128_ALERT_4_C Non-standard setting of Space group Pca21 .... Pc21b PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT430_ALERT_2_C Short Inter D...A Contact O11 .. O42 = 2.89 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C6 H3 N5 O6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.35 From the CIF: _reflns_number_total 851 Count of symmetry unique reflns 852 Completeness (_total/calc) 99.88% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
3 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 7 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Sheldrick, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1,3,4-trinitro-7,8-diazapentalene top
Crystal data top
C6H3N5O6Dx = 1.829 Mg m3
Dm = 0 Mg m3
Dm measured by not measured
Mr = 241.13Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pc21bCell parameters from 2958 reflections
a = 7.0098 (15) Åθ = 5.8–50.6°
b = 9.363 (2) ŵ = 0.17 mm1
c = 13.344 (3) ÅT = 93 K
V = 875.8 (3) Å3Chunk, red
Z = 40.35 × 0.22 × 0.13 mm
F(000) = 488
Data collection top
Bruker SMART CCD area-detector
diffractometer
851 independent reflections
Radiation source: fine-focus sealed tube795 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.102
φ and ω scansθmax = 25.4°, θmin = 2.9°
Absorption correction: multi-scan
(Sheldrick, 1999)
h = 88
Tmin = 0.190, Tmax = 0.981k = 1110
4530 measured reflectionsl = 1615
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0594P)2 + 0.2676P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max < 0.001
851 reflectionsΔρmax = 0.28 e Å3
155 parametersΔρmin = 0.34 e Å3
1 restraintExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.006 (4)
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.

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
C10.0210 (6)1.1250 (5)0.5789 (3)0.0172 (10)
N10.0540 (5)1.2135 (4)0.5012 (3)0.0189 (9)
O110.0596 (5)1.2597 (4)0.4384 (3)0.0261 (8)
O120.2252 (4)1.2397 (4)0.5033 (3)0.0238 (8)
C20.0634 (6)1.0841 (5)0.6673 (3)0.0164 (10)
H2A0.18841.10670.68970.020*
C30.0710 (6)1.0033 (5)0.7165 (3)0.0159 (10)
N30.0744 (5)0.9723 (4)0.8205 (3)0.0188 (8)
O310.0808 (5)0.9590 (4)0.8621 (2)0.0274 (8)
O320.2306 (4)0.9651 (4)0.8632 (2)0.0265 (8)
C40.4099 (6)0.9341 (5)0.6507 (3)0.0174 (10)
N40.4639 (5)0.8143 (4)0.7092 (3)0.0176 (9)
O410.3388 (4)0.7534 (4)0.7570 (3)0.0238 (8)
O420.6315 (5)0.7768 (4)0.7045 (3)0.0286 (9)
C50.4948 (6)0.9825 (5)0.5614 (3)0.0156 (9)
H5A0.61930.96030.53790.019*
C60.3633 (6)1.0679 (5)0.5149 (3)0.0171 (9)
H6A0.38051.11590.45280.021*
N70.2042 (5)1.0722 (4)0.5725 (3)0.0158 (8)
N80.2325 (5)0.9916 (4)0.6578 (3)0.0148 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.022 (2)0.014 (2)0.016 (2)0.0018 (19)0.0039 (19)0.0024 (18)
N10.025 (2)0.015 (2)0.0170 (19)0.0001 (17)0.0069 (19)0.0014 (17)
O110.0347 (19)0.028 (2)0.0156 (17)0.0029 (16)0.0030 (14)0.0056 (15)
O120.0247 (18)0.0202 (18)0.0264 (17)0.0045 (15)0.0070 (15)0.0015 (14)
C20.019 (2)0.015 (2)0.015 (2)0.0016 (18)0.0015 (17)0.0024 (19)
C30.020 (2)0.018 (3)0.009 (2)0.001 (2)0.0029 (15)0.0069 (18)
N30.026 (2)0.018 (2)0.0119 (17)0.0019 (16)0.0035 (16)0.0020 (16)
O310.0328 (17)0.030 (2)0.0194 (16)0.0039 (15)0.0133 (14)0.0033 (16)
O320.0334 (18)0.031 (2)0.0152 (16)0.0018 (16)0.0036 (14)0.0017 (14)
C40.016 (2)0.017 (2)0.020 (2)0.001 (2)0.0038 (17)0.0024 (19)
N40.022 (2)0.019 (2)0.0122 (17)0.0014 (17)0.0005 (16)0.0041 (16)
O410.0293 (16)0.0189 (17)0.0233 (16)0.0003 (15)0.0001 (16)0.0053 (15)
O420.0271 (19)0.034 (2)0.0244 (17)0.0133 (17)0.0017 (15)0.0069 (16)
C50.0147 (19)0.017 (2)0.0155 (19)0.0024 (19)0.0026 (16)0.0030 (19)
C60.020 (2)0.021 (2)0.0108 (19)0.004 (2)0.0011 (17)0.0006 (19)
N70.0224 (19)0.0156 (19)0.0092 (17)0.0036 (16)0.0032 (14)0.0018 (15)
N80.0224 (19)0.0119 (18)0.0099 (17)0.0023 (16)0.0033 (14)0.0021 (15)
Geometric parameters (Å, º) top
C1—C21.375 (6)C4—N81.359 (5)
C1—N71.379 (6)C4—C51.407 (6)
C1—N11.428 (6)C4—N41.417 (6)
N1—O121.225 (5)N4—O411.226 (5)
N1—O111.234 (5)N4—O421.227 (5)
C2—C31.375 (6)C5—C61.369 (7)
C2—H2A0.9500C5—H5A0.9500
C3—N81.381 (5)C6—N71.355 (5)
C3—N31.418 (6)C6—H6A0.9500
N3—O311.228 (5)N7—N81.380 (5)
N3—O321.236 (5)
C2—C1—N7110.7 (4)C5—C4—N4127.5 (4)
C2—C1—N1128.8 (4)O41—N4—O42125.3 (4)
N7—C1—N1120.4 (4)O41—N4—C4117.6 (4)
O12—N1—O11125.3 (4)O42—N4—C4117.0 (4)
O12—N1—C1117.4 (4)C6—C5—C4106.7 (4)
O11—N1—C1117.3 (4)C6—C5—H5A126.6
C3—C2—C1105.5 (4)C4—C5—H5A126.6
C3—C2—H2A127.2N7—C6—C5108.3 (4)
C1—C2—H2A127.2N7—C6—H6A125.8
C2—C3—N8109.6 (4)C5—C6—H6A125.8
C2—C3—N3126.2 (4)C6—N7—C1144.3 (4)
N8—C3—N3121.7 (4)C6—N7—N8109.5 (3)
O31—N3—O32124.8 (3)C1—N7—N8106.2 (3)
O31—N3—C3116.7 (3)C4—N8—N7106.9 (3)
O32—N3—C3118.5 (3)C4—N8—C3145.2 (4)
N8—C4—C5108.5 (4)N7—N8—C3107.8 (3)
N8—C4—N4121.3 (4)
C2—C1—N1—O1213.0 (7)C5—C6—N7—C1177.8 (6)
N7—C1—N1—O12169.4 (4)C5—C6—N7—N81.0 (5)
C2—C1—N1—O11165.7 (5)C2—C1—N7—C6179.0 (6)
N7—C1—N1—O1112.0 (6)N1—C1—N7—C61.0 (9)
N7—C1—C2—C30.3 (5)C2—C1—N7—N82.1 (5)
N1—C1—C2—C3178.1 (4)N1—C1—N7—N8179.8 (4)
C1—C2—C3—N81.8 (5)C5—C4—N8—N71.6 (5)
C1—C2—C3—N3160.3 (4)N4—C4—N8—N7161.2 (4)
C2—C3—N3—O3133.5 (7)C5—C4—N8—C3177.1 (6)
N8—C3—N3—O31166.4 (4)N4—C4—N8—C320.1 (9)
C2—C3—N3—O32144.3 (5)C6—N7—N8—C41.7 (5)
N8—C3—N3—O3215.8 (6)C1—N7—N8—C4177.6 (3)
N8—C4—N4—O418.9 (6)C6—N7—N8—C3177.6 (4)
C5—C4—N4—O41150.4 (4)C1—N7—N8—C33.2 (5)
N8—C4—N4—O42173.9 (4)C2—C3—N8—C4178.2 (6)
C5—C4—N4—O4226.8 (7)N3—C3—N8—C418.8 (9)
N8—C4—C5—C61.0 (5)C2—C3—N8—N73.1 (5)
N4—C4—C5—C6160.4 (4)N3—C3—N8—N7159.9 (4)
C4—C5—C6—N70.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O42i0.952.473.280 (5)143
C5—H5A···O32ii0.952.563.275 (5)132
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x1, y, z1/2.
 

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