Buy article online - an online subscription or single-article purchase is required to access this article.
The title compound, C
6HCl
3N
2O
4, is an intermediate in the synthesis of 1,3,5-trichloro-2,4,6-trinitrobenzene. The crystal structure at 153 K shows no major deviations from the previously reported structure at 295 K other than the expected contraction of the
a and
c axes and, correspondingly, the
angle.
Supporting information
CCDC reference: 153955
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL.
1,3,5-Trichloro-2,4-dinitrobenzene
top
Crystal data top
C6HCl3N2O4 | F(000) = 732 |
Mr = 271.44 | Dx = 1.902 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.933 (7) Å | Cell parameters from 999 reflections |
b = 9.328 (6) Å | θ = 2–25° |
c = 12.814 (9) Å | µ = 0.96 mm−1 |
β = 91.76 (4)° | T = 153 K |
V = 947.8 (12) Å3 | Prism, colourless |
Z = 4 | 0.36 × 0.28 × 0.26 mm |
Data collection top
Bruker AXS SMART diffractometer | 1315 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.074 |
Graphite monochromator | θmax = 26.5°, θmin = 2.6° |
ω–2θ scans | h = −7→9 |
5687 measured reflections | k = −11→11 |
1942 independent reflections | l = −14→16 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0729P)2] where P = (Fo2 + 2Fc2)/3 |
1942 reflections | (Δ/σ)max < 0.001 |
136 parameters | Δρmax = 0.77 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.49373 (14) | 0.23165 (12) | 0.09129 (8) | 0.0378 (3) | |
C1 | 0.7276 (5) | 0.0237 (4) | 0.0908 (3) | 0.0259 (9) | |
H1 | 0.7173 | 0.0267 | 0.0167 | 0.031* | |
Cl2 | 0.95696 (14) | −0.18278 (12) | 0.06791 (9) | 0.0364 (3) | |
C2 | 0.8371 (5) | −0.0705 (4) | 0.1404 (3) | 0.0253 (9) | |
Cl3 | 0.77463 (13) | 0.01355 (11) | 0.44296 (7) | 0.0296 (3) | |
C3 | 0.8524 (5) | −0.0747 (4) | 0.2492 (3) | 0.0230 (8) | |
C4 | 0.7576 (5) | 0.0175 (4) | 0.3092 (3) | 0.0237 (9) | |
C5 | 0.6486 (5) | 0.1104 (4) | 0.2583 (3) | 0.0244 (9) | |
C6 | 0.6325 (5) | 0.1143 (4) | 0.1518 (3) | 0.0253 (9) | |
N11 | 0.9690 (5) | −0.1741 (4) | 0.3008 (3) | 0.0351 (9) | |
O11 | 1.0971 (4) | −0.1258 (4) | 0.3409 (3) | 0.0535 (10) | |
O12 | 0.9280 (5) | −0.3001 (4) | 0.3011 (3) | 0.0535 (10) | |
O21 | 0.6000 (5) | 0.3267 (3) | 0.3372 (3) | 0.0492 (9) | |
N22 | 0.5451 (4) | 0.2070 (4) | 0.3213 (3) | 0.0296 (8) | |
O22 | 0.4143 (4) | 0.1598 (4) | 0.3533 (3) | 0.0428 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0428 (7) | 0.0377 (7) | 0.0326 (6) | 0.0123 (5) | −0.0060 (5) | 0.0087 (5) |
C1 | 0.028 (2) | 0.028 (2) | 0.021 (2) | −0.0068 (17) | −0.0009 (17) | 0.0016 (17) |
Cl2 | 0.0401 (7) | 0.0344 (6) | 0.0351 (6) | 0.0060 (5) | 0.0056 (5) | −0.0103 (5) |
C2 | 0.028 (2) | 0.017 (2) | 0.030 (2) | −0.0019 (16) | 0.0019 (17) | −0.0060 (17) |
Cl3 | 0.0373 (6) | 0.0285 (6) | 0.0228 (5) | 0.0044 (4) | −0.0043 (4) | −0.0006 (4) |
C3 | 0.026 (2) | 0.0158 (19) | 0.027 (2) | 0.0009 (15) | −0.0060 (16) | −0.0012 (16) |
C4 | 0.027 (2) | 0.023 (2) | 0.0214 (19) | −0.0018 (16) | −0.0037 (16) | 0.0020 (16) |
C5 | 0.025 (2) | 0.018 (2) | 0.030 (2) | 0.0018 (16) | −0.0011 (17) | −0.0020 (16) |
C6 | 0.025 (2) | 0.023 (2) | 0.028 (2) | −0.0008 (16) | −0.0069 (16) | 0.0053 (17) |
N11 | 0.041 (2) | 0.031 (2) | 0.033 (2) | 0.0121 (17) | −0.0020 (18) | −0.0061 (16) |
O11 | 0.042 (2) | 0.056 (2) | 0.061 (2) | 0.0120 (18) | −0.0219 (18) | −0.0105 (19) |
O12 | 0.064 (2) | 0.0270 (18) | 0.068 (3) | 0.0134 (17) | −0.009 (2) | 0.0046 (17) |
O21 | 0.067 (2) | 0.0243 (18) | 0.057 (2) | 0.0037 (16) | 0.0147 (19) | −0.0063 (16) |
N22 | 0.034 (2) | 0.031 (2) | 0.0242 (18) | 0.0077 (16) | −0.0030 (15) | 0.0002 (15) |
O22 | 0.0324 (18) | 0.054 (2) | 0.0422 (19) | 0.0031 (15) | 0.0072 (15) | −0.0058 (16) |
Geometric parameters (Å, º) top
Cl1—C6 | 1.720 (4) | C4—C5 | 1.374 (5) |
C1—C2 | 1.378 (6) | C5—C6 | 1.367 (6) |
C1—C6 | 1.389 (5) | C5—N22 | 1.476 (5) |
Cl2—C2 | 1.708 (4) | N11—O11 | 1.211 (5) |
C2—C3 | 1.396 (6) | N11—O12 | 1.220 (5) |
Cl3—C4 | 1.716 (4) | O21—N22 | 1.214 (5) |
C3—C4 | 1.390 (5) | N22—O22 | 1.210 (5) |
C3—N11 | 1.455 (5) | | |
| | | |
C2—C1—C6 | 118.3 (4) | C6—C5—N22 | 119.5 (3) |
C1—C2—C3 | 120.8 (4) | C4—C5—N22 | 118.5 (3) |
C1—C2—Cl2 | 119.6 (3) | C5—C6—C1 | 120.7 (4) |
C3—C2—Cl2 | 119.5 (3) | C5—C6—Cl1 | 120.4 (3) |
C4—C3—C2 | 120.2 (4) | C1—C6—Cl1 | 119.0 (3) |
C4—C3—N11 | 119.3 (3) | O11—N11—O12 | 125.3 (4) |
C2—C3—N11 | 120.4 (3) | O11—N11—C3 | 118.0 (4) |
C5—C4—C3 | 118.1 (4) | O12—N11—C3 | 116.7 (4) |
C5—C4—Cl3 | 121.1 (3) | O22—N22—O21 | 125.8 (3) |
C3—C4—Cl3 | 120.8 (3) | O22—N22—C5 | 117.5 (3) |
C6—C5—C4 | 121.9 (4) | O21—N22—C5 | 116.8 (3) |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
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.