1,5-Dichloro-2,4-dinitro­benzene

In the title compound, C₆H₂Cl₂N₂O, the two nitro groups are twisted away from the plane of the aromatic ring. Inter­molecular short Cl...O and Cl...Cl contacts are observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.061
• wR factor = 0.163
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O4      ..       3.16 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

1,5-dichloro-2,4-dinitrobenzene

Crystal data

C6H2Cl2N2O4	F(000) = 472
Mr = 237.00	Dx = 1.766 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.5900 (19) Å	θ = 10–14°
b = 6.5860 (13) Å	µ = 0.72 mm^−1
c = 14.751 (3) Å	T = 298 K
β = 106.86 (3)°	Needle, yellow
V = 891.6 (3) Å^3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	1065 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 26.0°, θmin = 2.2°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
Tmin = 0.814, Tmax = 0.932	l = −18→17
1845 measured reflections	3 standard reflections every 200 reflections
1739 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.163	w = 1/[σ^2(Fo^2) + (0.0612P)^2 + 0.8029P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
1739 reflections	Δρmax = 0.39 e Å^−3
128 parameters	Δρmin = −0.21 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.081 (7)

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
Cl1	0.86836 (16)	0.8072 (2)	0.51157 (9)	0.0803 (6)
Cl2	0.52778 (16)	0.1606 (2)	0.42287 (10)	0.0807 (6)
O1	0.6239 (4)	−0.0393 (5)	0.2774 (3)	0.0885 (13)
O2	0.6192 (4)	0.1645 (6)	0.1615 (3)	0.0870 (12)
O3	0.9089 (5)	0.7816 (9)	0.2416 (3)	0.1227 (19)
O4	1.0529 (4)	0.7729 (7)	0.3821 (3)	0.1004 (14)
N1	0.6402 (4)	0.1278 (6)	0.2447 (3)	0.0624 (11)
N2	0.9417 (4)	0.7272 (7)	0.3233 (3)	0.0672 (11)
C1	0.8048 (5)	0.6115 (7)	0.4339 (3)	0.0522 (11)
C2	0.8413 (4)	0.5881 (7)	0.3509 (3)	0.0484 (10)
C3	0.7831 (4)	0.4338 (7)	0.2888 (3)	0.0505 (11)
H3	0.8050	0.4233	0.2316	0.061*
C4	0.6926 (4)	0.2955 (6)	0.3121 (3)	0.0485 (10)
C5	0.6525 (5)	0.3152 (6)	0.3944 (3)	0.0505 (11)
C6	0.7088 (5)	0.4764 (7)	0.4544 (3)	0.0543 (12)
H6	0.6812	0.4934	0.5094	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0985 (11)	0.0792 (10)	0.0644 (8)	−0.0227 (8)	0.0254 (7)	−0.0246 (7)
Cl2	0.0986 (11)	0.0680 (9)	0.0870 (10)	−0.0193 (7)	0.0452 (8)	0.0154 (7)
O1	0.111 (3)	0.048 (2)	0.102 (3)	−0.010 (2)	0.023 (2)	−0.008 (2)
O2	0.119 (3)	0.082 (3)	0.059 (2)	−0.013 (2)	0.024 (2)	−0.017 (2)
O3	0.109 (3)	0.180 (5)	0.082 (3)	−0.055 (3)	0.033 (3)	0.030 (3)
O4	0.080 (3)	0.125 (4)	0.094 (3)	−0.044 (3)	0.021 (2)	−0.010 (3)
N1	0.066 (3)	0.052 (3)	0.070 (3)	−0.001 (2)	0.021 (2)	−0.011 (2)
N2	0.058 (3)	0.084 (3)	0.063 (3)	−0.016 (2)	0.024 (2)	−0.002 (2)
C1	0.055 (3)	0.054 (3)	0.046 (2)	−0.002 (2)	0.013 (2)	0.001 (2)
C2	0.046 (2)	0.050 (3)	0.050 (2)	0.000 (2)	0.0163 (19)	0.005 (2)
C3	0.050 (3)	0.058 (3)	0.047 (2)	0.006 (2)	0.020 (2)	0.000 (2)
C4	0.048 (2)	0.045 (2)	0.053 (2)	0.003 (2)	0.015 (2)	0.000 (2)
C5	0.055 (3)	0.047 (2)	0.051 (2)	−0.002 (2)	0.018 (2)	0.011 (2)
C6	0.068 (3)	0.058 (3)	0.042 (2)	0.000 (2)	0.023 (2)	0.004 (2)

Geometric parameters (Å, º)

Cl1—C1	1.714 (5)	C1—C6	1.376 (6)
Cl2—C5	1.713 (4)	C1—C2	1.377 (6)
O1—N1	1.230 (5)	C2—C3	1.373 (6)
O2—N1	1.208 (5)	C3—C4	1.368 (6)
O3—N2	1.209 (5)	C3—H3	0.93
O4—N2	1.201 (5)	C4—C5	1.382 (6)
N1—C4	1.473 (6)	C5—C6	1.388 (6)
N2—C2	1.469 (6)	C6—H6	0.93
O2—N1—O1	125.0 (4)	C4—C3—C2	119.4 (4)
O2—N1—C4	117.3 (4)	C4—C3—H3	120.3
O1—N1—C4	117.6 (4)	C2—C3—H3	120.3
O4—N2—O3	124.5 (5)	C3—C4—C5	121.1 (4)
O4—N2—C2	118.2 (4)	C3—C4—N1	116.5 (4)
O3—N2—C2	117.3 (4)	C5—C4—N1	122.4 (4)
C6—C1—C2	118.8 (4)	C4—C5—C6	118.5 (4)
C6—C1—Cl1	118.0 (3)	C4—C5—Cl2	123.5 (4)
C2—C1—Cl1	123.1 (4)	C6—C5—Cl2	117.9 (3)
C3—C2—C1	121.1 (4)	C1—C6—C5	121.1 (4)
C3—C2—N2	116.7 (4)	C1—C6—H6	119.5
C1—C2—N2	122.2 (4)	C5—C6—H6	119.5
C6—C1—C2—C3	0.3 (7)	O2—N1—C4—C3	−33.8 (6)
Cl1—C1—C2—C3	−177.3 (3)	O1—N1—C4—C3	144.9 (4)
C6—C1—C2—N2	179.3 (4)	O2—N1—C4—C5	145.8 (4)
Cl1—C1—C2—N2	1.7 (6)	O1—N1—C4—C5	−35.6 (6)
O4—N2—C2—C3	−135.2 (5)	C3—C4—C5—C6	−1.4 (6)
O3—N2—C2—C3	42.0 (7)	N1—C4—C5—C6	179.1 (4)
O4—N2—C2—C1	45.8 (7)	C3—C4—C5—Cl2	174.2 (3)
O3—N2—C2—C1	−137.0 (5)	N1—C4—C5—Cl2	−5.3 (6)
C1—C2—C3—C4	−3.1 (6)	C2—C1—C6—C5	1.9 (7)
N2—C2—C3—C4	177.9 (4)	Cl1—C1—C6—C5	179.6 (3)
C2—C3—C4—C5	3.6 (6)	C4—C5—C6—C1	−1.4 (7)
C2—C3—C4—N1	−176.8 (4)	Cl2—C5—C6—C1	−177.3 (4)