Dichloro­bis(2,4-dichloro-5-fluoro­phen­yl)methane

The molecule of the title compound, C₁₃H₄Cl₆F₂, has twofold crystallographic symmetry, with the axis passing through the central methlyene C atom. The dihedral angle between the two aromatic residues is 86.13 (8)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.088
• Data-to-parameter ratio = 12.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  F1      ..       3.07 Ang.

   0 ALERT level A = In general: serious problem
   0 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
   1 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

Dichlorobis(2,4-dichloro-5-fluorophenyl)methane

Crystal data

C13H4Cl6F2	F(000) = 808.00
Mr = 410.89	Dx = 1.806 Mg m^−3
Orthorhombic, Pnna	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2a 2bc	Cell parameters from 10723 reflections
a = 19.896 (9) Å	θ = 3.1–27.6°
b = 11.483 (4) Å	µ = 1.14 mm^−1
c = 6.614 (2) Å	T = 298 K
V = 1510.9 (10) Å^3	Block, colorless
Z = 4	0.43 × 0.33 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1186 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.037
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −25→25
Tmin = 0.613, Tmax = 0.710	k = −14→14
13211 measured reflections	l = −8→8
1734 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0007Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.033	(Δ/σ)max < 0.001
wR(F^2) = 0.088	Δρmax = 0.32 e Å^−3
S = 1.02	Δρmin = −0.33 e Å^−3
1189 reflections	Extinction correction: Larson (1970), equation 22
97 parameters	Extinction coefficient: 40 (2)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 2.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.09298 (4)	0.34402 (6)	0.53467 (9)	0.0611 (2)
Cl2	0.05197 (6)	0.67907 (6)	−0.00764 (17)	0.0956 (3)
Cl3	0.26111 (4)	0.19831 (6)	0.05320 (11)	0.0704 (2)
F1	0.16106 (9)	0.56424 (13)	−0.2275 (2)	0.0836 (5)
C1	0.11564 (12)	0.40418 (19)	0.3046 (3)	0.0454 (5)
C2	0.08103 (12)	0.5036 (2)	0.2475 (3)	0.0564 (7)
C3	0.09582 (13)	0.5571 (2)	0.0676 (4)	0.0594 (7)
C4	0.14532 (14)	0.5115 (2)	−0.0501 (3)	0.0576 (7)
C5	0.17995 (12)	0.4129 (2)	0.0027 (3)	0.0521 (6)
C6	0.16602 (12)	0.35645 (18)	0.1833 (3)	0.0438 (5)
C7	0.20614 (17)	0.2500	0.2500	0.0481 (8)
H2	0.0477	0.5340	0.3309	0.068*
H5	0.2129	0.3836	−0.0833	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0743 (4)	0.0577 (3)	0.0512 (3)	0.0027 (3)	0.0176 (3)	0.0051 (2)
Cl2	0.1107 (7)	0.0643 (4)	0.1120 (6)	0.0165 (4)	−0.0228 (5)	0.0247 (4)
Cl3	0.0579 (4)	0.0750 (4)	0.0784 (4)	0.0081 (3)	0.0225 (3)	−0.0053 (3)
F1	0.1165 (14)	0.0743 (10)	0.0600 (9)	−0.0246 (9)	0.0019 (9)	0.0260 (7)
C1	0.0497 (13)	0.0443 (11)	0.0422 (11)	−0.0063 (10)	0.0018 (10)	0.0003 (10)
C2	0.0572 (15)	0.0488 (13)	0.0631 (14)	−0.0005 (11)	0.0032 (12)	−0.0005 (12)
C3	0.0634 (17)	0.0468 (13)	0.0680 (17)	−0.0056 (12)	−0.0110 (13)	0.0092 (12)
C4	0.0724 (19)	0.0525 (14)	0.0478 (12)	−0.0183 (13)	−0.0063 (12)	0.0117 (12)
C5	0.0548 (15)	0.0556 (14)	0.0460 (11)	−0.0117 (11)	0.0063 (11)	0.0010 (10)
C6	0.0432 (12)	0.0446 (11)	0.0438 (11)	−0.0068 (9)	−0.0011 (9)	−0.0009 (9)
C7	0.0431 (18)	0.0553 (18)	0.0458 (16)	0.0000	0.0000	−0.0016 (14)

Geometric parameters (Å, º)

Cl1—C1	1.731 (2)	C3—C4	1.360 (3)
Cl2—C3	1.723 (2)	C4—C5	1.371 (3)
Cl3—C7	1.801 (2)	C5—C6	1.386 (3)
F1—C4	1.357 (2)	C6—C7	1.525 (2)
C1—C2	1.386 (3)	C2—H2	0.930
C1—C6	1.396 (3)	C5—H5	0.930
C2—C3	1.371 (3)
Cl1···Cl1	3.5741 (8)	Cl2···H2	3.497
Cl1···Cl2	3.4616 (13)	Cl3···H5	3.386
Cl1···F1	3.2715 (17)	F1···H5	2.750
Cl1···C4	3.511 (2)	C4···H5	3.076
Cl2···Cl1	3.4616 (13)	C5···H5	3.215
Cl2···Cl2	3.5959 (15)	H2···Cl1	3.254
Cl3···F1	3.0671 (17)	H2···Cl2	3.497
F1···Cl1	3.2715 (17)	H2···H2	3.036
F1···Cl3	3.0671 (17)	H5···Cl1	3.504
F1···C5	3.521 (3)	H5···Cl3	3.386
C4···Cl1	3.511 (2)	H5···F1	2.750
C5···F1	3.521 (3)	H5···C4	3.076
C5···C5	3.431 (3)	H5···C5	3.215
Cl1···H2	3.254	H5···H5	3.056
Cl1···H5	3.504
Cl1—C1—C2	116.05 (17)	C1—C6—C7	121.60 (18)
Cl1—C1—C6	122.39 (16)	C5—C6—C7	121.3 (2)
C2—C1—C6	121.6 (2)	Cl3—C7—Cl3	105.20 (17)
C1—C2—C3	119.9 (2)	Cl3—C7—C6	111.89 (8)
Cl2—C3—C2	120.4 (2)	Cl3—C7—C6	105.24 (8)
Cl2—C3—C4	120.9 (2)	Cl3—C7—C6	105.24 (8)
C2—C3—C4	118.7 (2)	Cl3—C7—C6	111.89 (8)
F1—C4—C3	119.4 (2)	C6—C7—C6	116.9 (2)
F1—C4—C5	118.2 (2)	C1—C2—H2	120.1
C3—C4—C5	122.4 (2)	C3—C2—H2	120.0
C4—C5—C6	120.3 (2)	C4—C5—H5	119.8
C1—C6—C5	117.1 (2)	C6—C5—H5	119.9
Cl1—C1—C2—C3	179.91 (19)	C2—C3—C4—C5	1.3 (4)
Cl1—C1—C6—C5	−179.62 (18)	F1—C4—C5—C6	179.5 (2)
Cl1—C1—C6—C7	−2.2 (3)	C3—C4—C5—C6	−1.1 (4)
C2—C1—C6—C5	−0.0 (2)	C4—C5—C6—C1	0.4 (3)
C2—C1—C6—C7	177.4 (2)	C4—C5—C6—C7	−177.0 (2)
C6—C1—C2—C3	0.3 (3)	C1—C6—C7—Cl3	173.74 (18)
C1—C2—C3—Cl2	178.66 (19)	C1—C6—C7—Cl3	−72.5 (2)
C1—C2—C3—C4	−0.9 (3)	C1—C6—C7—C6	52.3 (2)
Cl2—C3—C4—F1	1.2 (3)	C5—C6—C7—Cl3	−8.9 (2)
Cl2—C3—C4—C5	−178.2 (2)	C5—C6—C7—Cl3	104.8 (2)
C2—C3—C4—F1	−179.3 (2)	C5—C6—C7—C6	−130.4 (2)