Crystal structure and Hirshfeld surface analysis of (2E)-1-(3-bromo­phen­yl)-3-(4-fluoro­phen­yl)prop-2-en-1-one

In the title compound, the 3-bromo­phenyl and 4-fluoro­phenyl rings, linked via a prop-2-en-1-one spacer, make a dihedral angle of 48.90 (15)°. In the crystal, mol­ecules are linked by C—H...π inter­actions between the bromo­phenyl and fluoro­phenyl rings of mol­ecules, resulting in a two-dimensional layered structure parallel to the ab plane.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.105
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         39 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         13 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   2 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

(2E)-1-(3-Bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one

Crystal data

C15H10BrFO	Z = 2
Mr = 305.14	F(000) = 304
Triclinic, P1	Dx = 1.608 Mg m^−3
a = 5.9255 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5867 (8) Å	Cell parameters from 4763 reflections
c = 14.1427 (15) Å	θ = 3.6–27.3°
α = 89.774 (2)°	µ = 3.26 mm^−1
β = 82.671 (2)°	T = 294 K
γ = 87.712 (2)°	Block, colourless
V = 630.09 (11) Å^3	0.30 × 0.28 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer	2101 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2007)	θmax = 26.0°, θmin = 1.5°
Tmin = 0.398, Tmax = 0.431	h = −7→7
9618 measured reflections	k = −7→9
2442 independent reflections	l = −17→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0481P)^2 + 0.4984P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
2442 reflections	Δρmax = 0.76 e Å^−3
163 parameters	Δρmin = −0.40 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Br1	1.29286 (6)	0.37541 (6)	0.08193 (2)	0.06864 (18)
F1	0.2394 (4)	−0.0245 (4)	0.91227 (16)	0.0855 (7)
O1	1.2246 (4)	0.2758 (4)	0.46700 (17)	0.0609 (6)
C1	0.7494 (5)	0.4234 (4)	0.3499 (2)	0.0485 (7)
H1A	0.639101	0.432526	0.402871	0.058*
C2	0.7020 (5)	0.4863 (5)	0.2621 (3)	0.0553 (8)
H2A	0.560236	0.540073	0.257032	0.066*
C3	0.8602 (5)	0.4709 (4)	0.1826 (2)	0.0530 (8)
H3A	0.825976	0.511138	0.123703	0.064*
C4	1.0720 (5)	0.3940 (4)	0.1920 (2)	0.0440 (6)
C5	1.1280 (5)	0.3320 (4)	0.2783 (2)	0.0408 (6)
H5A	1.271938	0.281871	0.283008	0.049*
C6	0.9640 (5)	0.3463 (4)	0.3583 (2)	0.0401 (6)
C7	1.0259 (5)	0.2821 (4)	0.4522 (2)	0.0453 (7)
C8	0.8399 (5)	0.2254 (4)	0.5237 (2)	0.0491 (7)
H8A	0.697720	0.207874	0.504874	0.059*
C9	0.8697 (5)	0.1987 (4)	0.6141 (2)	0.0437 (6)
H9A	1.012966	0.220989	0.630447	0.052*
C10	0.7013 (5)	0.1380 (4)	0.6910 (2)	0.0402 (6)
C11	0.7434 (5)	0.1542 (4)	0.7850 (2)	0.0479 (7)
H11A	0.878507	0.202032	0.797670	0.058*
C12	0.5888 (6)	0.1008 (5)	0.8598 (2)	0.0585 (8)
H12A	0.617731	0.112494	0.922560	0.070*
C13	0.3923 (6)	0.0304 (5)	0.8394 (2)	0.0550 (8)
C14	0.3445 (5)	0.0080 (4)	0.7482 (2)	0.0500 (7)
H14A	0.211180	−0.044035	0.736707	0.060*
C15	0.4981 (5)	0.0640 (4)	0.6738 (2)	0.0456 (7)
H15A	0.466180	0.052442	0.611505	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0651 (3)	0.0932 (3)	0.0443 (2)	0.00443 (19)	0.00298 (15)	0.01381 (18)
F1	0.0780 (15)	0.117 (2)	0.0573 (13)	−0.0210 (14)	0.0140 (11)	0.0172 (13)
O1	0.0431 (12)	0.0916 (19)	0.0486 (13)	−0.0062 (12)	−0.0076 (9)	0.0087 (12)
C1	0.0376 (14)	0.0507 (18)	0.0559 (18)	−0.0022 (13)	−0.0009 (13)	−0.0040 (14)
C2	0.0405 (15)	0.0551 (19)	0.072 (2)	0.0047 (14)	−0.0157 (15)	0.0050 (16)
C3	0.0502 (17)	0.0548 (19)	0.0564 (19)	−0.0041 (14)	−0.0162 (14)	0.0139 (15)
C4	0.0426 (14)	0.0470 (16)	0.0416 (15)	−0.0025 (13)	−0.0023 (12)	0.0043 (12)
C5	0.0359 (13)	0.0421 (15)	0.0444 (15)	−0.0014 (12)	−0.0049 (11)	0.0028 (12)
C6	0.0368 (13)	0.0397 (15)	0.0442 (15)	−0.0062 (11)	−0.0052 (11)	−0.0003 (12)
C7	0.0435 (15)	0.0490 (17)	0.0440 (15)	−0.0073 (13)	−0.0059 (12)	−0.0013 (13)
C8	0.0437 (15)	0.0570 (19)	0.0474 (17)	−0.0093 (14)	−0.0067 (13)	0.0011 (14)
C9	0.0398 (14)	0.0441 (16)	0.0468 (16)	−0.0008 (12)	−0.0048 (12)	0.0003 (13)
C10	0.0418 (14)	0.0342 (14)	0.0445 (15)	0.0027 (11)	−0.0062 (12)	0.0009 (12)
C11	0.0460 (16)	0.0496 (17)	0.0495 (17)	−0.0009 (13)	−0.0117 (13)	0.0032 (13)
C12	0.065 (2)	0.071 (2)	0.0397 (16)	−0.0030 (17)	−0.0085 (14)	0.0045 (15)
C13	0.0530 (18)	0.060 (2)	0.0490 (18)	0.0006 (15)	0.0050 (14)	0.0107 (15)
C14	0.0425 (15)	0.0476 (17)	0.0597 (19)	−0.0055 (13)	−0.0049 (13)	0.0022 (14)
C15	0.0478 (16)	0.0470 (17)	0.0424 (15)	−0.0023 (13)	−0.0071 (12)	−0.0008 (13)

Geometric parameters (Å, º)

Br1—C4	1.903 (3)	C8—C9	1.327 (4)
F1—C13	1.358 (4)	C8—H8A	0.9300
O1—C7	1.221 (4)	C9—C10	1.465 (4)
C1—C2	1.387 (5)	C9—H9A	0.9300
C1—C6	1.397 (4)	C10—C11	1.390 (4)
C1—H1A	0.9300	C10—C15	1.398 (4)
C2—C3	1.371 (5)	C11—C12	1.379 (5)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.384 (4)	C12—C13	1.364 (5)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.382 (4)	C13—C14	1.368 (5)
C5—C6	1.396 (4)	C14—C15	1.378 (4)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.496 (4)	C15—H15A	0.9300
C7—C8	1.474 (4)
C2—C1—C6	119.6 (3)	C7—C8—H8A	119.1
C2—C1—H1A	120.2	C8—C9—C10	127.1 (3)
C6—C1—H1A	120.2	C8—C9—H9A	116.5
C3—C2—C1	121.2 (3)	C10—C9—H9A	116.5
C3—C2—H2A	119.4	C11—C10—C15	118.2 (3)
C1—C2—H2A	119.4	C11—C10—C9	119.2 (3)
C2—C3—C4	118.6 (3)	C15—C10—C9	122.5 (3)
C2—C3—H3A	120.7	C12—C11—C10	121.3 (3)
C4—C3—H3A	120.7	C12—C11—H11A	119.3
C5—C4—C3	122.2 (3)	C10—C11—H11A	119.3
C5—C4—Br1	119.3 (2)	C13—C12—C11	118.3 (3)
C3—C4—Br1	118.5 (2)	C13—C12—H12A	120.9
C4—C5—C6	118.6 (3)	C11—C12—H12A	120.9
C4—C5—H5A	120.7	F1—C13—C12	119.0 (3)
C6—C5—H5A	120.7	F1—C13—C14	118.2 (3)
C5—C6—C1	119.8 (3)	C12—C13—C14	122.8 (3)
C5—C6—C7	118.6 (3)	C13—C14—C15	118.6 (3)
C1—C6—C7	121.5 (3)	C13—C14—H14A	120.7
O1—C7—C8	122.3 (3)	C15—C14—H14A	120.7
O1—C7—C6	120.2 (3)	C14—C15—C10	120.7 (3)
C8—C7—C6	117.5 (2)	C14—C15—H15A	119.6
C9—C8—C7	121.9 (3)	C10—C15—H15A	119.6
C9—C8—H8A	119.1
C6—C1—C2—C3	1.5 (5)	C6—C7—C8—C9	−166.9 (3)
C1—C2—C3—C4	−1.4 (5)	C7—C8—C9—C10	−178.2 (3)
C2—C3—C4—C5	0.3 (5)	C8—C9—C10—C11	−165.8 (3)
C2—C3—C4—Br1	−179.2 (3)	C8—C9—C10—C15	14.1 (5)
C3—C4—C5—C6	0.7 (5)	C15—C10—C11—C12	−0.7 (5)
Br1—C4—C5—C6	−179.9 (2)	C9—C10—C11—C12	179.2 (3)
C4—C5—C6—C1	−0.6 (4)	C10—C11—C12—C13	0.3 (5)
C4—C5—C6—C7	−179.0 (3)	C11—C12—C13—F1	179.3 (3)
C2—C1—C6—C5	−0.5 (4)	C11—C12—C13—C14	1.2 (6)
C2—C1—C6—C7	177.9 (3)	F1—C13—C14—C15	179.7 (3)
C5—C6—C7—O1	25.1 (4)	C12—C13—C14—C15	−2.1 (5)
C1—C6—C7—O1	−153.3 (3)	C13—C14—C15—C10	1.7 (5)
C5—C6—C7—C8	−154.0 (3)	C11—C10—C15—C14	−0.3 (5)
C1—C6—C7—C8	27.6 (4)	C9—C10—C15—C14	179.8 (3)
O1—C7—C8—C9	14.0 (5)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the 3-bromophenyl (C1–C6) and 4-fluorophenyl (C10–C15) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.53	2.840 (4)	100
C2—H2A···Cg2^i	0.93	2.93	3.571 (4)	127
C5—H5A···Cg2^ii	0.93	2.98	3.642 (3)	129
C14—H14A···Cg1^iii	0.93	2.90	3.590 (3)	132

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