4′-Fluoro­chalcone

The enone fragment and the benzene rings of the title compound, C₁₅H₁₁FO, are each planar. The crystal packing is stabilized by weak inter­molecular C—H...π inter­actions involving both aromatic rings; the mol­ecules are stacked along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.154
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.847     0.990
            Tmin(prime) and Tmax expected:      0.964     0.991
            RR(prime) =      0.879
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A    ..  CG2     ..       2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A    ..  CG1     ..       3.08 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

4'-Fluorochalcone

Crystal data

C15H11FO	Z = 2
Mr = 226.24	F(000) = 236
Triclinic, P1	Dx = 1.342 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.8391 (2) Å	Cell parameters from 1274 reflections
b = 7.4435 (3) Å	θ = 1.6–27.5°
c = 13.0358 (5) Å	µ = 0.09 mm^−1
α = 96.592 (2)°	T = 100 K
β = 93.947 (2)°	Block, yellow
γ = 93.593 (2)°	0.38 × 0.30 × 0.10 mm
V = 560.07 (4) Å^3

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	2538 independent reflections
Radiation source: fine-focus sealed tube	1843 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 8.33 pixels mm^-1	θmax = 27.5°, θmin = 1.6°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.847, Tmax = 0.991	l = −16→16
6883 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0877P)^2] where P = (Fo^2 + 2Fc^2)/3
2538 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

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
F1	0.6929 (2)	−0.11348 (16)	−0.44819 (9)	0.0358 (3)
O1	1.2117 (2)	0.20886 (18)	−0.02319 (10)	0.0284 (3)
C1	0.6909 (3)	0.0308 (2)	−0.17421 (14)	0.0230 (4)
H1A	0.5921	0.0280	−0.1213	0.028*
C2	0.6172 (3)	−0.0478 (2)	−0.27336 (15)	0.0240 (4)
H2A	0.4712	−0.1063	−0.2875	0.029*
C3	0.7654 (3)	−0.0372 (2)	−0.35048 (14)	0.0246 (4)
C4	0.9861 (3)	0.0456 (2)	−0.33364 (15)	0.0258 (4)
H4A	1.0817	0.0516	−0.3875	0.031*
C5	1.0583 (3)	0.1190 (2)	−0.23375 (14)	0.0231 (4)
H5A	1.2070	0.1727	−0.2198	0.028*
C6	0.9134 (3)	0.1144 (2)	−0.15310 (14)	0.0211 (4)
C7	1.0035 (3)	0.1967 (2)	−0.04711 (14)	0.0222 (4)
C8	0.8377 (3)	0.2675 (2)	0.02584 (14)	0.0234 (4)
H8A	0.6852	0.2757	0.0022	0.028*
C9	0.9055 (3)	0.3195 (2)	0.12531 (14)	0.0224 (4)
H9A	1.0566	0.3000	0.1460	0.027*
C10	0.7698 (3)	0.4038 (2)	0.20571 (14)	0.0212 (4)
C11	0.8602 (3)	0.4264 (2)	0.30877 (14)	0.0235 (4)
H11A	1.0031	0.3842	0.3254	0.028*
C12	0.7396 (3)	0.5111 (2)	0.38695 (14)	0.0260 (4)
H12A	0.8011	0.5244	0.4553	0.031*
C13	0.5275 (3)	0.5757 (2)	0.36246 (15)	0.0267 (4)
H13A	0.4476	0.6343	0.4143	0.032*
C14	0.4345 (3)	0.5530 (2)	0.26079 (14)	0.0241 (4)
H14A	0.2915	0.5953	0.2447	0.029*
C15	0.5536 (3)	0.4675 (2)	0.18263 (14)	0.0225 (4)
H15B	0.4895	0.4524	0.1146	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0348 (7)	0.0401 (7)	0.0292 (6)	−0.0050 (5)	0.0033 (5)	−0.0063 (5)
O1	0.0200 (7)	0.0331 (7)	0.0315 (7)	0.0014 (6)	0.0022 (5)	0.0010 (6)
C1	0.0191 (9)	0.0224 (9)	0.0289 (10)	0.0023 (7)	0.0059 (7)	0.0059 (7)
C2	0.0190 (9)	0.0195 (8)	0.0331 (10)	−0.0012 (7)	0.0020 (7)	0.0028 (7)
C3	0.0274 (10)	0.0216 (8)	0.0241 (9)	0.0030 (8)	0.0019 (7)	−0.0011 (7)
C4	0.0245 (10)	0.0240 (9)	0.0297 (10)	0.0008 (8)	0.0092 (8)	0.0028 (7)
C5	0.0186 (9)	0.0183 (8)	0.0325 (10)	0.0006 (7)	0.0046 (7)	0.0027 (7)
C6	0.0185 (9)	0.0176 (8)	0.0279 (9)	0.0028 (7)	0.0032 (7)	0.0040 (7)
C7	0.0201 (9)	0.0204 (8)	0.0268 (10)	0.0024 (7)	0.0029 (7)	0.0042 (7)
C8	0.0185 (9)	0.0224 (9)	0.0298 (10)	0.0020 (7)	0.0035 (7)	0.0039 (7)
C9	0.0182 (9)	0.0184 (8)	0.0311 (10)	0.0008 (7)	0.0033 (7)	0.0043 (7)
C10	0.0197 (9)	0.0161 (8)	0.0274 (9)	−0.0024 (7)	0.0038 (7)	0.0022 (7)
C11	0.0198 (9)	0.0211 (8)	0.0296 (10)	−0.0012 (7)	0.0007 (7)	0.0048 (7)
C12	0.0242 (10)	0.0275 (9)	0.0260 (10)	−0.0031 (8)	0.0029 (7)	0.0039 (7)
C13	0.0233 (10)	0.0240 (9)	0.0323 (10)	−0.0021 (8)	0.0088 (8)	−0.0003 (7)
C14	0.0175 (9)	0.0189 (8)	0.0363 (11)	−0.0008 (7)	0.0052 (7)	0.0046 (7)
C15	0.0202 (9)	0.0205 (8)	0.0266 (9)	−0.0024 (7)	0.0013 (7)	0.0041 (7)

Geometric parameters (Å, º)

F1—C3	1.361 (2)	C8—H8A	0.9300
O1—C7	1.229 (2)	C9—C10	1.465 (2)
C1—C2	1.384 (3)	C9—H9A	0.9300
C1—C6	1.401 (3)	C10—C11	1.397 (3)
C1—H1A	0.9300	C10—C15	1.401 (2)
C2—C3	1.376 (3)	C11—C12	1.393 (3)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.385 (3)	C12—C13	1.387 (3)
C4—C5	1.380 (3)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.385 (3)
C5—C6	1.396 (2)	C13—H13A	0.9300
C5—H5A	0.9300	C14—C15	1.390 (2)
C6—C7	1.492 (3)	C14—H14A	0.9300
C7—C8	1.481 (2)	C15—H15B	0.9300
C8—C9	1.335 (3)
C2—C1—C6	120.34 (17)	C7—C8—H8A	119.7
C2—C1—H1A	119.8	C8—C9—C10	127.65 (17)
C6—C1—H1A	119.8	C8—C9—H9A	116.2
C3—C2—C1	118.42 (17)	C10—C9—H9A	116.2
C3—C2—H2A	120.8	C11—C10—C15	118.47 (16)
C1—C2—H2A	120.8	C11—C10—C9	119.29 (16)
F1—C3—C2	118.53 (17)	C15—C10—C9	122.22 (17)
F1—C3—C4	118.13 (16)	C12—C11—C10	120.97 (17)
C2—C3—C4	123.33 (17)	C12—C11—H11A	119.5
C5—C4—C3	117.35 (17)	C10—C11—H11A	119.5
C5—C4—H4A	121.3	C13—C12—C11	119.76 (18)
C3—C4—H4A	121.3	C13—C12—H12A	120.1
C4—C5—C6	121.53 (17)	C11—C12—H12A	120.1
C4—C5—H5A	119.2	C14—C13—C12	119.98 (16)
C6—C5—H5A	119.2	C14—C13—H13A	120.0
C5—C6—C1	118.99 (17)	C12—C13—H13A	120.0
C5—C6—C7	118.50 (16)	C13—C14—C15	120.43 (17)
C1—C6—C7	122.50 (16)	C13—C14—H14A	119.8
O1—C7—C8	121.62 (16)	C15—C14—H14A	119.8
O1—C7—C6	119.85 (15)	C14—C15—C10	120.38 (17)
C8—C7—C6	118.50 (16)	C14—C15—H15B	119.8
C9—C8—C7	120.52 (17)	C10—C15—H15B	119.8
C9—C8—H8A	119.7
C6—C1—C2—C3	−1.7 (3)	O1—C7—C8—C9	−11.1 (3)
C1—C2—C3—F1	−179.63 (15)	C6—C7—C8—C9	170.87 (16)
C1—C2—C3—C4	1.0 (3)	C7—C8—C9—C10	175.35 (16)
F1—C3—C4—C5	−178.73 (15)	C8—C9—C10—C11	171.32 (17)
C2—C3—C4—C5	0.6 (3)	C8—C9—C10—C15	−10.5 (3)
C3—C4—C5—C6	−1.6 (3)	C15—C10—C11—C12	−0.4 (3)
C4—C5—C6—C1	1.0 (3)	C9—C10—C11—C12	177.92 (16)
C4—C5—C6—C7	−179.92 (15)	C10—C11—C12—C13	−0.6 (3)
C2—C1—C6—C5	0.7 (3)	C11—C12—C13—C14	1.1 (3)
C2—C1—C6—C7	−178.32 (16)	C12—C13—C14—C15	−0.7 (3)
C5—C6—C7—O1	−25.2 (2)	C13—C14—C15—C10	−0.3 (3)
C1—C6—C7—O1	153.85 (17)	C11—C10—C15—C14	0.8 (3)
C5—C6—C7—C8	152.85 (16)	C9—C10—C15—C14	−177.44 (16)
C1—C6—C7—C8	−28.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···Cg2^i	0.93	2.90	3.528 (2)	126
C5—H5A···Cg2^ii	0.93	2.84	3.442 (2)	123
C9—H9A···Cg1^iii	0.93	3.08	3.639 (2)	120
C14—H14A···Cg1^iv	0.93	2.87	3.536 (2)	129
C9—H9A···O1	0.93	2.48	2.814 (2)	101

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, −y+1, −z; (iii) −x+2, −y, −z; (iv) −x+1, −y+1, −z.