The title compound, C12H3Cl6NO2, has a dihedral angle of 83.92 (8)° between the benzene rings. It was obtained as an intermediate in the synthesis of 3-hydroxy PCB 136 by nitration of PCB 136.
Supporting information
CCDC reference: 298355
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.042
- wR factor = 0.100
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT430_ALERT_2_A Short Inter D...A Contact O1' .. O1' .. 1.98 Ang.
| Author Response: The CIFCHECK program appears to have generated an alert
because of close contact between a disordered oxygen atom in a
minor-component (12% occupancy) nitrate group and a symmetry generated
copy of itself. No such close contact exists in the actual structure,
it is simply a consequence of the nature of the disorder. The
_publ_section_exptl_refinement section contains a description of the
disorder.
|
PLAT431_ALERT_2_A Short Inter HL..A Contact Cl2' .. O2' .. 2.70 Ang.
| Author Response: This short contact is between a minor component (12%) of a
disordered Cl atom and a symmetry-generated copy of an oxygen on a
minor component (12%) nitrate group. Given the low-occupancy factor
for these minor components and the fact that they are superimposed
on the major components, their refined coordinates are expected to
be of low accuracy. One has to be careful with restraints
during least-squares refinement to maintain a chemically sensible
model, and in this case, use of the normal battery of SAME, SADI etc.
restraints was not quite able to keep the geometry of the minor
component as similar as we would like to that of the major component.
Since the minor component is so small (12%), the major component is
clearly the most important. The corresponding contact for the major
component counterpart of this is 2.983, which although a bit short
is a much more sensible value. The nature of the disorder is
described in the _publ_section_exptl_refinement section. Clearly
the least-squares process has a difficult time simultaneously refining
the position of 12% of a nitrate superimposed on 88% of a Cl and 12%
of a Cl superimposed on 88% of a nitrate. Further refinement with
tighter restraints or constraints on minor component geometry do not
yield any further insights into the structure of this compound.
|
Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact C5 .. O2' .. 2.91 Ang.
Alert level C
PLAT301_ALERT_3_C Main Residue Disorder ......................... 16.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2 .. O2 .. 2.98 Ang.
| Author Response: This short contact is between a minor component (12%) of a
disordered Cl atom and a symmetry-generated copy of an oxygen on a
minor component (12%) nitrate group. Given the low-occupancy factor
for these minor components and the fact that they are superimposed
on the major components, their refined coordinates are expected to
be of low accuracy. One has to be careful with restraints
during least-squares refinement to maintain a chemically sensible
model, and in this case, use of the normal battery of SAME, SADI etc.
restraints was not quite able to keep the geometry of the minor
component as similar as we would like to that of the major component.
Since the minor component is so small (12%), the major component is
clearly the most important. The corresponding contact for the major
component counterpart of this is 2.983, which although a bit short
is a much more sensible value. The nature of the disorder is
described in the _publ_section_exptl_refinement section. Clearly
the least-squares process has a difficult time simultaneously refining
the position of 12% of a nitrate superimposed on 88% of a Cl and 12%
of a Cl superimposed on 88% of a nitrate. Further refinement with
tighter restraints or constraints on minor component geometry do not
yield any further insights into the structure of this compound.
|
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl5 .. O1 .. 3.14 Ang.
| Author Response: This short contact is between a minor component (12%) of a
disordered Cl atom and a symmetry-generated copy of an oxygen on a
minor component (12%) nitrate group. Given the low-occupancy factor
for these minor components and the fact that they are superimposed
on the major components, their refined coordinates are expected to
be of low accuracy. One has to be careful with restraints
during least-squares refinement to maintain a chemically sensible
model, and in this case, use of the normal battery of SAME, SADI etc.
restraints was not quite able to keep the geometry of the minor
component as similar as we would like to that of the major component.
Since the minor component is so small (12%), the major component is
clearly the most important. The corresponding contact for the major
component counterpart of this is 2.983, which although a bit short
is a much more sensible value. The nature of the disorder is
described in the _publ_section_exptl_refinement section. Clearly
the least-squares process has a difficult time simultaneously refining
the position of 12% of a nitrate superimposed on 88% of a Cl and 12%
of a Cl superimposed on 88% of a nitrate. Further refinement with
tighter restraints or constraints on minor component geometry do not
yield any further insights into the structure of this compound.
|
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl6 .. O1' .. 3.01 Ang.
| Author Response: This short contact is between a minor component (12%) of a
disordered Cl atom and a symmetry-generated copy of an oxygen on a
minor component (12%) nitrate group. Given the low-occupancy factor
for these minor components and the fact that they are superimposed
on the major components, their refined coordinates are expected to
be of low accuracy. One has to be careful with restraints
during least-squares refinement to maintain a chemically sensible
model, and in this case, use of the normal battery of SAME, SADI etc.
restraints was not quite able to keep the geometry of the minor
component as similar as we would like to that of the major component.
Since the minor component is so small (12%), the major component is
clearly the most important. The corresponding contact for the major
component counterpart of this is 2.983, which although a bit short
is a much more sensible value. The nature of the disorder is
described in the _publ_section_exptl_refinement section. Clearly
the least-squares process has a difficult time simultaneously refining
the position of 12% of a nitrate superimposed on 88% of a Cl and 12%
of a Cl superimposed on 88% of a nitrate. Further refinement with
tighter restraints or constraints on minor component geometry do not
yield any further insights into the structure of this compound.
|
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl2' .. O2' .. 3.11 Ang.
| Author Response: This short contact is between a minor component (12%) of a
disordered Cl atom and a symmetry-generated copy of an oxygen on a
minor component (12%) nitrate group. Given the low-occupancy factor
for these minor components and the fact that they are superimposed
on the major components, their refined coordinates are expected to
be of low accuracy. One has to be careful with restraints
during least-squares refinement to maintain a chemically sensible
model, and in this case, use of the normal battery of SAME, SADI etc.
restraints was not quite able to keep the geometry of the minor
component as similar as we would like to that of the major component.
Since the minor component is so small (12%), the major component is
clearly the most important. The corresponding contact for the major
component counterpart of this is 2.983, which although a bit short
is a much more sensible value. The nature of the disorder is
described in the _publ_section_exptl_refinement section. Clearly
the least-squares process has a difficult time simultaneously refining
the position of 12% of a nitrate superimposed on 88% of a Cl and 12%
of a Cl superimposed on 88% of a nitrate. Further refinement with
tighter restraints or constraints on minor component geometry do not
yield any further insights into the structure of this compound.
|
PLAT432_ALERT_2_C Short Inter X...Y Contact C4 .. O1' .. 2.93 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 2.00 Deg.
N1' -C3 -CL2 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 9.20 Deg.
N1 -C5 -CL2' 1.555 1.555 1.555
2 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
8 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
10 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
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.
2,2',3,3',6,6'-Hexachloro-5-nitro-1,1'-biphenyl
top
Crystal data top
C12H3Cl6NO2 | F(000) = 800 |
Mr = 405.85 | Dx = 1.879 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3326 reflections |
a = 12.1073 (2) Å | θ = 1.0–27.5° |
b = 16.3810 (5) Å | µ = 1.20 mm−1 |
c = 7.5813 (4) Å | T = 90 K |
β = 107.4219 (14)° | Block cut from rod, yellow |
V = 1434.62 (9) Å3 | 0.25 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 3280 independent reflections |
Radiation source: fine-focus sealed tube | 2544 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 1.8° |
ω scans at fixed χ = 55° | h = −15→15 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −21→21 |
Tmin = 0.742, Tmax = 0.796 | l = −9→9 |
5940 measured reflections | |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0381P)2 + 1.8622P] where P = (Fo2 + 2Fc2)/3 |
3280 reflections | (Δ/σ)max = 0.002 |
207 parameters | Δρmax = 0.65 e Å−3 |
20 restraints | Δρmin = −0.41 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. The ring with the NO2 substituent is disordered. This was modelled with major
and minor components for the Cl and the NO2. Some resraints were used to
maintain the geometry of the disordered parts. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cl1 | 0.32816 (6) | −0.04170 (4) | 0.50062 (9) | 0.02591 (18) | |
Cl2 | 0.0854 (2) | −0.07297 (11) | 0.2114 (2) | 0.0259 (4) | 0.880 (4) |
N1' | 0.084 (6) | −0.0615 (8) | 0.231 (3) | 0.026 (17)* | 0.120 (4) |
O1' | 0.0407 (15) | −0.0472 (10) | 0.072 (2) | 0.028 (5)* | 0.120 (4) |
O2' | 0.1057 (16) | −0.1253 (10) | 0.315 (2) | 0.032 (5)* | 0.120 (4) |
Cl3 | 0.17149 (7) | 0.23375 (5) | 0.72135 (10) | 0.03124 (19) | |
Cl4 | 0.43141 (6) | 0.17323 (5) | 0.49570 (9) | 0.02545 (18) | |
Cl5 | 0.66240 (6) | 0.19969 (5) | 0.82349 (10) | 0.02769 (18) | |
Cl6 | 0.23880 (6) | 0.03511 (5) | 0.97899 (9) | 0.02959 (19) | |
N1 | −0.0637 (4) | 0.1921 (3) | 0.4076 (8) | 0.0272 (12) | 0.880 (4) |
O1 | −0.1546 (2) | 0.1641 (2) | 0.3258 (5) | 0.0582 (10) | 0.880 (4) |
O2 | −0.0451 (2) | 0.2622 (2) | 0.4636 (5) | 0.0490 (9) | 0.880 (4) |
Cl2' | −0.0639 (11) | 0.2133 (7) | 0.410 (2) | 0.025 (3)* | 0.120 (4) |
C1 | 0.2343 (2) | 0.09375 (17) | 0.5985 (4) | 0.0189 (6) | |
C2 | 0.2167 (2) | 0.02602 (17) | 0.4817 (3) | 0.0191 (6) | |
C3 | 0.1100 (2) | 0.01338 (17) | 0.3488 (4) | 0.0198 (6) | |
C4 | 0.0220 (2) | 0.06932 (18) | 0.3288 (4) | 0.0215 (6) | |
H4 | −0.0505 | 0.0610 | 0.2378 | 0.026* | |
C5 | 0.0392 (2) | 0.13725 (18) | 0.4410 (4) | 0.0209 (6) | |
C6 | 0.1448 (2) | 0.15058 (17) | 0.5764 (4) | 0.0197 (6) | |
C1' | 0.3459 (2) | 0.10483 (16) | 0.7497 (4) | 0.0189 (6) | |
C2' | 0.4419 (2) | 0.14049 (17) | 0.7173 (4) | 0.0200 (6) | |
C3' | 0.5445 (2) | 0.15131 (17) | 0.8597 (4) | 0.0220 (6) | |
C4' | 0.5523 (2) | 0.12411 (18) | 1.0359 (4) | 0.0230 (6) | |
H4' | 0.6227 | 0.1303 | 1.1328 | 0.028* | |
C5' | 0.4582 (2) | 0.08809 (18) | 1.0717 (4) | 0.0232 (6) | |
H5' | 0.4636 | 0.0695 | 1.1926 | 0.028* | |
C6' | 0.3556 (2) | 0.07930 (18) | 0.9293 (4) | 0.0212 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0222 (4) | 0.0262 (4) | 0.0250 (3) | 0.0058 (3) | 0.0005 (3) | −0.0037 (3) |
Cl2 | 0.0232 (7) | 0.0271 (6) | 0.0254 (6) | −0.0056 (5) | 0.0042 (5) | −0.0053 (5) |
Cl3 | 0.0256 (4) | 0.0321 (4) | 0.0321 (4) | 0.0059 (3) | 0.0027 (3) | −0.0111 (3) |
Cl4 | 0.0214 (4) | 0.0321 (4) | 0.0220 (3) | −0.0025 (3) | 0.0052 (3) | 0.0045 (3) |
Cl5 | 0.0170 (4) | 0.0309 (4) | 0.0335 (4) | −0.0041 (3) | 0.0051 (3) | −0.0004 (3) |
Cl6 | 0.0231 (4) | 0.0439 (5) | 0.0211 (3) | −0.0090 (3) | 0.0057 (3) | 0.0017 (3) |
N1 | 0.020 (2) | 0.024 (3) | 0.035 (2) | −0.0032 (19) | 0.0040 (13) | 0.000 (2) |
O1 | 0.0174 (15) | 0.063 (2) | 0.081 (2) | 0.0083 (14) | −0.0059 (14) | −0.0288 (18) |
O2 | 0.0272 (16) | 0.0280 (18) | 0.080 (2) | 0.0077 (12) | −0.0015 (14) | −0.0067 (17) |
C1 | 0.0147 (14) | 0.0235 (15) | 0.0189 (12) | −0.0036 (11) | 0.0056 (10) | 0.0017 (11) |
C2 | 0.0164 (14) | 0.0228 (15) | 0.0174 (12) | −0.0002 (11) | 0.0042 (10) | 0.0028 (11) |
C3 | 0.0201 (14) | 0.0220 (14) | 0.0178 (12) | −0.0055 (12) | 0.0066 (11) | −0.0020 (11) |
C4 | 0.0129 (14) | 0.0308 (16) | 0.0191 (13) | −0.0033 (12) | 0.0021 (10) | 0.0022 (12) |
C5 | 0.0144 (14) | 0.0260 (15) | 0.0214 (13) | 0.0034 (11) | 0.0040 (11) | 0.0036 (12) |
C6 | 0.0177 (14) | 0.0231 (15) | 0.0190 (13) | −0.0026 (11) | 0.0068 (11) | 0.0003 (11) |
C1' | 0.0167 (14) | 0.0190 (14) | 0.0193 (13) | 0.0025 (11) | 0.0026 (11) | −0.0035 (11) |
C2' | 0.0208 (14) | 0.0195 (14) | 0.0193 (13) | 0.0030 (11) | 0.0054 (11) | 0.0004 (11) |
C3' | 0.0178 (14) | 0.0202 (15) | 0.0273 (14) | 0.0014 (11) | 0.0057 (11) | −0.0035 (12) |
C4' | 0.0175 (14) | 0.0237 (15) | 0.0232 (14) | 0.0023 (11) | −0.0010 (11) | −0.0012 (11) |
C5' | 0.0216 (15) | 0.0260 (16) | 0.0192 (13) | 0.0006 (12) | 0.0020 (11) | 0.0001 (11) |
C6' | 0.0180 (14) | 0.0222 (15) | 0.0225 (13) | −0.0007 (11) | 0.0048 (11) | 0.0000 (11) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.719 (3) | C1—C1' | 1.498 (4) |
Cl2—C3 | 1.729 (3) | C2—C3 | 1.395 (4) |
N1'—O1' | 1.182 (18) | C3—C4 | 1.379 (4) |
N1'—O2' | 1.211 (18) | C4—C5 | 1.378 (4) |
N1'—C3 | 1.494 (6) | C4—H4 | 0.9500 |
Cl3—C6 | 1.719 (3) | C5—C6 | 1.397 (4) |
Cl4—C2' | 1.731 (3) | C1'—C2' | 1.388 (4) |
Cl5—C3' | 1.724 (3) | C1'—C6' | 1.395 (4) |
Cl6—C6' | 1.727 (3) | C2'—C3' | 1.392 (4) |
N1—O1 | 1.183 (6) | C3'—C4' | 1.385 (4) |
N1—O2 | 1.222 (7) | C4'—C5' | 1.380 (4) |
N1—C5 | 1.494 (6) | C4'—H4' | 0.9500 |
Cl2'—C5 | 1.729 (3) | C5'—C6' | 1.388 (4) |
C1—C2 | 1.396 (4) | C5'—H5' | 0.9500 |
C1—C6 | 1.400 (4) | | |
| | | |
O1'—N1'—O2' | 131.9 (14) | C4—C5—Cl2' | 121.9 (6) |
O1'—N1'—C3 | 113.3 (15) | C6—C5—Cl2' | 116.9 (6) |
O2'—N1'—C3 | 114.8 (16) | N1—C5—Cl2' | 9.2 (7) |
O1—N1—O2 | 126.3 (5) | C5—C6—C1 | 119.3 (2) |
O1—N1—C5 | 117.0 (5) | C5—C6—Cl3 | 123.3 (2) |
O2—N1—C5 | 116.7 (4) | C1—C6—Cl3 | 117.4 (2) |
C2—C1—C6 | 119.1 (2) | C2'—C1'—C6' | 118.0 (2) |
C2—C1—C1' | 120.9 (2) | C2'—C1'—C1 | 121.8 (2) |
C6—C1—C1' | 119.9 (2) | C6'—C1'—C1 | 120.3 (2) |
C3—C2—C1 | 120.6 (2) | C1'—C2'—C3' | 121.1 (2) |
C3—C2—Cl1 | 119.9 (2) | C1'—C2'—Cl4 | 118.7 (2) |
C1—C2—Cl1 | 119.5 (2) | C3'—C2'—Cl4 | 120.2 (2) |
C4—C3—C2 | 119.9 (2) | C4'—C3'—C2' | 119.6 (3) |
C4—C3—N1' | 117 (2) | C4'—C3'—Cl5 | 118.8 (2) |
C2—C3—N1' | 123 (2) | C2'—C3'—Cl5 | 121.6 (2) |
C4—C3—Cl2 | 119.3 (2) | C5'—C4'—C3' | 120.4 (3) |
C2—C3—Cl2 | 120.8 (2) | C5'—C4'—H4' | 119.8 |
N1'—C3—Cl2 | 2 (3) | C3'—C4'—H4' | 119.8 |
C5—C4—C3 | 120.0 (2) | C4'—C5'—C6' | 119.4 (3) |
C5—C4—H4 | 120.0 | C4'—C5'—H5' | 120.3 |
C3—C4—H4 | 120.0 | C6'—C5'—H5' | 120.3 |
C4—C5—C6 | 121.1 (3) | C5'—C6'—C1' | 121.5 (3) |
C4—C5—N1 | 114.6 (3) | C5'—C6'—Cl6 | 118.3 (2) |
C6—C5—N1 | 124.3 (3) | C1'—C6'—Cl6 | 120.2 (2) |
| | | |
C6—C1—C2—C3 | −2.3 (4) | N1—C5—C6—Cl3 | −1.3 (5) |
C1'—C1—C2—C3 | 175.9 (2) | Cl2'—C5—C6—Cl3 | 5.0 (6) |
C6—C1—C2—Cl1 | 177.1 (2) | C2—C1—C6—C5 | 1.5 (4) |
C1'—C1—C2—Cl1 | −4.8 (4) | C1'—C1—C6—C5 | −176.7 (2) |
C1—C2—C3—C4 | 1.8 (4) | C2—C1—C6—Cl3 | −179.1 (2) |
Cl1—C2—C3—C4 | −177.5 (2) | C1'—C1—C6—Cl3 | 2.8 (3) |
C1—C2—C3—N1' | −175 (2) | C2—C1—C1'—C2' | 84.4 (4) |
Cl1—C2—C3—N1' | 6 (2) | C6—C1—C1'—C2' | −97.5 (3) |
C1—C2—C3—Cl2 | −176.8 (2) | C2—C1—C1'—C6' | −95.8 (3) |
Cl1—C2—C3—Cl2 | 3.9 (3) | C6—C1—C1'—C6' | 82.4 (3) |
O1'—N1'—C3—C4 | 51 (6) | C6'—C1'—C2'—C3' | −0.7 (4) |
O2'—N1'—C3—C4 | −127 (4) | C1—C1'—C2'—C3' | 179.2 (3) |
O1'—N1'—C3—C2 | −132 (4) | C6'—C1'—C2'—Cl4 | −179.6 (2) |
O2'—N1'—C3—C2 | 50 (6) | C1—C1'—C2'—Cl4 | 0.3 (4) |
C2—C3—C4—C5 | −0.5 (4) | C1'—C2'—C3'—C4' | 1.8 (4) |
N1'—C3—C4—C5 | 176 (2) | Cl4—C2'—C3'—C4' | −179.4 (2) |
Cl2—C3—C4—C5 | 178.1 (2) | C1'—C2'—C3'—Cl5 | −177.0 (2) |
C3—C4—C5—C6 | −0.3 (4) | Cl4—C2'—C3'—Cl5 | 1.9 (3) |
C3—C4—C5—N1 | −178.9 (3) | C2'—C3'—C4'—C5' | −1.4 (4) |
C3—C4—C5—Cl2' | 174.8 (6) | Cl5—C3'—C4'—C5' | 177.4 (2) |
O1—N1—C5—C4 | 17.9 (6) | C3'—C4'—C5'—C6' | 0.0 (4) |
O2—N1—C5—C4 | −160.2 (4) | C4'—C5'—C6'—C1' | 1.1 (4) |
O1—N1—C5—C6 | −160.6 (4) | C4'—C5'—C6'—Cl6 | −179.2 (2) |
O2—N1—C5—C6 | 21.3 (7) | C2'—C1'—C6'—C5' | −0.8 (4) |
C4—C5—C6—C1 | −0.2 (4) | C1—C1'—C6'—C5' | 179.4 (3) |
N1—C5—C6—C1 | 178.2 (3) | C2'—C1'—C6'—Cl6 | 179.6 (2) |
Cl2'—C5—C6—C1 | −175.5 (6) | C1—C1'—C6'—Cl6 | −0.3 (4) |
C4—C5—C6—Cl3 | −179.7 (2) | | |