2,6-Di­fluoro­benzo­nitrile

2,6-Difluorobenzonitrile packs in slightly puckered molecular sheets (mol­ecules tilted 4.1 (2)° with respect to the sheets). All of the H atoms in the mol­ecule are in contact with N and F atoms in adjacent mol­ecules in the sheet.

Key indicators

• Single-crystal X-ray study
• T = 174 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.120
• Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C7      ..       5.31 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C7     ...       1.43 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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.

2,6-Difluorobenzonitrile

Crystal data

C7H3F2N	Z = 2
Mr = 139.10	F(000) = 140
Triclinic, P1	Dx = 1.505 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8164 (17) Å	Cell parameters from 1641 reflections
b = 7.2165 (18) Å	θ = 3.2–27.4°
c = 7.2951 (18) Å	µ = 0.13 mm^−1
α = 111.40 (1)°	T = 174 K
β = 104.57 (1)°	Cut needle, colorless
γ = 101.06 (1)°	0.50 × 0.50 × 0.45 mm
V = 306.93 (13) Å^3

Data collection

Siemens area detector diffractometer	1040 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 26.0°, θmin = 3.2°
ω scans	h = −8→8
1769 measured reflections	k = −7→8
1144 independent reflections	l = −8→8

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)] = 0.039	All H-atom parameters refined
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.071P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max = 0.001
1144 reflections	Δρmax = 0.21 e Å^−3
104 parameters	Δρmin = −0.22 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 1.22 (9)

Special details

Experimental. When the data collection was about 60% complete, the crystal shattered, indicating a phase change had taken place. Since there were enough data for an acceptable determination, another crystal was not used.

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

	x	y	z	Uiso*/Ueq
C1	0.2519 (2)	0.3933 (2)	0.6701 (2)	0.0320 (4)
C2	0.2677 (2)	0.5566 (2)	0.6105 (2)	0.0353 (4)
F2	0.27881 (16)	0.51572 (15)	0.41887 (14)	0.0485 (4)
C3	0.2698 (3)	0.7522 (2)	0.7371 (3)	0.0416 (4)
H3	0.279 (3)	0.857 (3)	0.687 (3)	0.052 (5)*
C4	0.2566 (2)	0.7870 (2)	0.9327 (2)	0.0409 (4)
H4	0.257 (3)	0.923 (3)	1.025 (3)	0.057 (5)*
C5	0.2425 (2)	0.6308 (2)	1.0011 (2)	0.0368 (4)
H5	0.239 (3)	0.657 (3)	1.140 (3)	0.049 (5)*
C6	0.2406 (2)	0.4375 (2)	0.8690 (2)	0.0323 (4)
F6	0.22844 (15)	0.28246 (13)	0.93013 (13)	0.0436 (4)
C7	0.2474 (2)	0.1900 (2)	0.5328 (2)	0.0384 (4)
N1	0.2425 (3)	0.0278 (2)	0.4227 (2)	0.0535 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0314 (7)	0.0354 (8)	0.0282 (7)	0.0095 (6)	0.0101 (5)	0.0138 (6)
C2	0.0358 (8)	0.0440 (9)	0.0285 (7)	0.0098 (6)	0.0114 (5)	0.0194 (6)
F2	0.0627 (7)	0.0590 (7)	0.0324 (5)	0.0175 (5)	0.0209 (4)	0.0272 (5)
C3	0.0456 (9)	0.0380 (9)	0.0440 (9)	0.0114 (7)	0.0134 (7)	0.0234 (7)
C4	0.0428 (8)	0.0351 (8)	0.0384 (8)	0.0100 (7)	0.0129 (6)	0.0113 (7)
C5	0.0370 (8)	0.0419 (9)	0.0285 (7)	0.0095 (6)	0.0128 (6)	0.0126 (6)
C6	0.0322 (7)	0.0361 (8)	0.0309 (7)	0.0083 (6)	0.0108 (5)	0.0184 (6)
F6	0.0585 (6)	0.0429 (6)	0.0389 (6)	0.0156 (4)	0.0207 (4)	0.0257 (4)
C7	0.0443 (8)	0.0432 (9)	0.0308 (7)	0.0146 (7)	0.0149 (6)	0.0177 (7)
N1	0.0759 (11)	0.0443 (9)	0.0403 (8)	0.0238 (8)	0.0244 (7)	0.0134 (7)

Geometric parameters (Å, º)

C1—C2	1.392 (2)	C4—C5	1.387 (2)
C1—C6	1.393 (2)	C4—H4	0.97 (2)
C1—C7	1.433 (2)	C5—C6	1.371 (2)
C2—F2	1.3449 (18)	C5—H5	0.96 (2)
C2—C3	1.371 (2)	C6—F6	1.3437 (16)
C3—C4	1.385 (2)	C7—N1	1.1407 (19)
C3—H3	0.95 (2)
C2—C1—C6	116.74 (13)	C3—C4—H4	119.8 (12)
C2—C1—C7	121.39 (13)	C5—C4—H4	118.5 (12)
C6—C1—C7	121.87 (13)	C6—C5—C4	118.23 (14)
F2—C2—C3	119.93 (13)	C6—C5—H5	120.3 (11)
F2—C2—C1	117.24 (13)	C4—C5—H5	121.4 (11)
C3—C2—C1	122.83 (14)	F6—C6—C5	120.00 (13)
C2—C3—C4	117.98 (14)	F6—C6—C1	117.50 (13)
C2—C3—H3	118.9 (11)	C5—C6—C1	122.49 (13)
C4—C3—H3	123.1 (11)	N1—C7—C1	179.55 (17)
C3—C4—C5	121.72 (15)