1-(4-Bromo­phenyl)-3-(3-hydroxy­phenyl)prop-2-en-1-one

The title mol­ecule, C₁₅H₁₁BrO₂, is approximately planar and the dihedral angle between the two aromatic rings is 10.2 (2)°. The H atoms of the central enone moiety are trans. The mol­ecules form centrosymmetric hydrogen-bonded dimers via intermolecular O—H...O hydrogen bonds (H...O = 2.02 Å and O—H...O = 172°).

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.091
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br1     ..       3.58 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14    ..  CG1     ..       3.02 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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 and PLATON (Spek, 2003).

1-(4-Bromophenyl)-3-(3-hydroxyphenyl)prop-2-ene-1-one

Crystal data

C15H11BrO2	F(000) = 608
Mr = 303.15	Dx = 1.557 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2004 reflections
a = 11.7495 (13) Å	θ = 2.5–27.6°
b = 5.4876 (6) Å	µ = 3.17 mm^−1
c = 20.165 (2) Å	T = 293 K
β = 95.918 (2)°	Block, colourless
V = 1293.2 (2) Å^3	0.23 × 0.16 × 0.12 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	2538 independent reflections
Radiation source: fine-focus sealed tube	1905 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω scans	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.514, Tmax = 0.686	k = −4→6
6678 measured reflections	l = −24→23

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0356P)^2 + 0.6438P] where P = (Fo^2 + 2Fc^2)/3
2538 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.46 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
Br1	0.00624 (3)	0.06073 (8)	0.087423 (15)	0.08419 (18)
O1	0.32757 (18)	0.5202 (4)	0.35878 (10)	0.0633 (6)
O2	0.54835 (17)	0.0805 (4)	0.68682 (9)	0.0609 (5)
H2	0.5796	0.2053	0.6755	0.091*
C1	0.4431 (2)	0.1437 (5)	0.57977 (11)	0.0435 (6)
H1	0.4818	0.2892	0.5746	0.052*
C2	0.4674 (2)	0.0093 (5)	0.63716 (12)	0.0454 (6)
C3	0.4110 (2)	−0.2072 (5)	0.64535 (13)	0.0500 (6)
H3	0.4282	−0.3002	0.6836	0.060*
C4	0.3283 (2)	−0.2845 (5)	0.59570 (13)	0.0522 (7)
H4	0.2889	−0.4287	0.6015	0.063*
C5	0.3034 (2)	−0.1516 (5)	0.53795 (13)	0.0494 (6)
H5	0.2483	−0.2067	0.5050	0.059*
C6	0.3615 (2)	0.0656 (5)	0.52940 (11)	0.0409 (6)
C7	0.3434 (2)	0.2125 (5)	0.46901 (12)	0.0453 (6)
H7	0.3821	0.3606	0.4702	0.054*
C8	0.2798 (2)	0.1635 (5)	0.41302 (12)	0.0469 (6)
H8	0.2353	0.0229	0.4102	0.056*
C9	0.2771 (2)	0.3249 (5)	0.35488 (12)	0.0448 (6)
C10	0.21330 (19)	0.2493 (5)	0.29038 (12)	0.0410 (6)
C11	0.1497 (2)	0.0378 (5)	0.28260 (14)	0.0533 (7)
H11	0.1478	−0.0681	0.3185	0.064*
C12	0.0886 (3)	−0.0191 (5)	0.22213 (15)	0.0586 (7)
H12	0.0452	−0.1610	0.2174	0.070*
C13	0.0929 (2)	0.1361 (6)	0.16952 (12)	0.0515 (7)
C14	0.1568 (3)	0.3429 (6)	0.17499 (13)	0.0621 (8)
H14	0.1603	0.4451	0.1385	0.075*
C15	0.2166 (2)	0.3987 (5)	0.23567 (13)	0.0541 (7)
H15	0.2602	0.5405	0.2397	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0802 (3)	0.1233 (4)	0.0446 (2)	−0.0086 (2)	−0.01476 (15)	−0.01742 (17)
O1	0.0770 (13)	0.0521 (12)	0.0557 (12)	−0.0210 (10)	−0.0179 (10)	0.0048 (9)
O2	0.0706 (13)	0.0701 (14)	0.0385 (10)	−0.0045 (10)	−0.0114 (9)	0.0026 (9)
C1	0.0482 (14)	0.0434 (15)	0.0381 (13)	0.0012 (11)	0.0013 (10)	−0.0021 (11)
C2	0.0463 (13)	0.0525 (17)	0.0373 (13)	0.0068 (12)	0.0043 (11)	−0.0038 (11)
C3	0.0574 (15)	0.0538 (17)	0.0399 (13)	0.0117 (14)	0.0102 (11)	0.0058 (12)
C4	0.0552 (15)	0.0468 (16)	0.0560 (16)	−0.0020 (13)	0.0132 (13)	0.0026 (13)
C5	0.0504 (14)	0.0512 (16)	0.0457 (14)	−0.0012 (13)	0.0007 (11)	−0.0048 (12)
C6	0.0447 (13)	0.0421 (14)	0.0352 (12)	0.0065 (11)	0.0010 (10)	−0.0026 (10)
C7	0.0484 (13)	0.0426 (15)	0.0434 (13)	−0.0012 (12)	−0.0027 (11)	−0.0010 (11)
C8	0.0488 (13)	0.0478 (15)	0.0420 (13)	−0.0079 (12)	−0.0045 (11)	−0.0007 (12)
C9	0.0412 (13)	0.0461 (15)	0.0452 (14)	0.0008 (12)	−0.0042 (10)	0.0004 (12)
C10	0.0374 (12)	0.0445 (15)	0.0400 (12)	0.0012 (11)	−0.0011 (10)	−0.0002 (11)
C11	0.0589 (16)	0.0500 (16)	0.0474 (15)	−0.0081 (13)	−0.0122 (12)	0.0087 (12)
C12	0.0617 (17)	0.0545 (18)	0.0558 (17)	−0.0117 (14)	−0.0119 (13)	−0.0035 (13)
C13	0.0461 (14)	0.071 (2)	0.0356 (13)	−0.0019 (14)	−0.0018 (10)	−0.0101 (12)
C14	0.0727 (18)	0.079 (2)	0.0340 (13)	−0.0132 (17)	0.0033 (12)	0.0062 (14)
C15	0.0607 (16)	0.0588 (18)	0.0419 (14)	−0.0149 (14)	0.0010 (12)	0.0023 (12)

Geometric parameters (Å, º)

Br1—C13	1.898 (2)	C7—C8	1.316 (3)
O1—C9	1.223 (3)	C7—H7	0.93
O2—C2	1.365 (3)	C8—C9	1.467 (4)
O2—H2	0.82	C8—H8	0.93
C1—C2	1.377 (3)	C9—C10	1.492 (3)
C1—C6	1.390 (3)	C10—C15	1.378 (3)
C1—H1	0.93	C10—C11	1.381 (4)
C2—C3	1.378 (4)	C11—C12	1.385 (4)
C3—C4	1.388 (4)	C11—H11	0.93
C3—H3	0.93	C12—C13	1.366 (4)
C4—C5	1.380 (4)	C12—H12	0.93
C4—H4	0.93	C13—C14	1.359 (4)
C5—C6	1.393 (4)	C14—C15	1.381 (4)
C5—H5	0.93	C14—H14	0.93
C6—C7	1.458 (3)	C15—H15	0.93
C2—O2—H2	109.5	C7—C8—H8	119.2
C2—C1—C6	121.1 (2)	C9—C8—H8	119.2
C2—C1—H1	119.5	O1—C9—C8	120.5 (2)
C6—C1—H1	119.5	O1—C9—C10	119.8 (2)
O2—C2—C1	122.1 (2)	C8—C9—C10	119.7 (2)
O2—C2—C3	117.8 (2)	C15—C10—C11	118.0 (2)
C1—C2—C3	120.1 (2)	C15—C10—C9	118.6 (2)
C2—C3—C4	119.1 (2)	C11—C10—C9	123.4 (2)
C2—C3—H3	120.4	C10—C11—C12	121.0 (3)
C4—C3—H3	120.4	C10—C11—H11	119.5
C5—C4—C3	121.3 (3)	C12—C11—H11	119.5
C5—C4—H4	119.4	C13—C12—C11	119.1 (3)
C3—C4—H4	119.4	C13—C12—H12	120.5
C4—C5—C6	119.5 (2)	C11—C12—H12	120.5
C4—C5—H5	120.2	C14—C13—C12	121.5 (2)
C6—C5—H5	120.2	C14—C13—Br1	119.7 (2)
C1—C6—C5	118.9 (2)	C12—C13—Br1	118.8 (2)
C1—C6—C7	118.0 (2)	C13—C14—C15	118.9 (3)
C5—C6—C7	123.1 (2)	C13—C14—H14	120.5
C8—C7—C6	128.6 (3)	C15—C14—H14	120.5
C8—C7—H7	115.7	C10—C15—C14	121.6 (3)
C6—C7—H7	115.7	C10—C15—H15	119.2
C7—C8—C9	121.7 (2)	C14—C15—H15	119.2
C6—C1—C2—O2	179.0 (2)	O1—C9—C10—C15	2.5 (4)
C6—C1—C2—C3	0.3 (4)	C8—C9—C10—C15	−176.9 (2)
O2—C2—C3—C4	−180.0 (2)	O1—C9—C10—C11	−176.8 (3)
C1—C2—C3—C4	−1.2 (4)	C8—C9—C10—C11	3.8 (4)
C2—C3—C4—C5	1.4 (4)	C15—C10—C11—C12	−1.7 (4)
C3—C4—C5—C6	−0.6 (4)	C9—C10—C11—C12	177.6 (3)
C2—C1—C6—C5	0.5 (4)	C10—C11—C12—C13	0.8 (5)
C2—C1—C6—C7	−177.7 (2)	C11—C12—C13—C14	0.8 (5)
C4—C5—C6—C1	−0.3 (4)	C11—C12—C13—Br1	−178.6 (2)
C4—C5—C6—C7	177.7 (2)	C12—C13—C14—C15	−1.4 (5)
C1—C6—C7—C8	172.9 (3)	Br1—C13—C14—C15	178.0 (2)
C5—C6—C7—C8	−5.1 (4)	C11—C10—C15—C14	1.2 (4)
C6—C7—C8—C9	−175.7 (2)	C9—C10—C15—C14	−178.1 (3)
C7—C8—C9—O1	−5.8 (4)	C13—C14—C15—C10	0.4 (5)
C7—C8—C9—C10	173.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82	2.02	2.837 (3)	172
C7—H7···O1	0.93	2.43	2.782 (3)	102
C12—H12···Cg2^ii	0.93	2.78	3.482 (4)	132
C14—H14···Cg1^iii	0.93	3.02	3.590 (3)	121

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