1-(4-Bromo­phen­yl)-3-(2,5-dimethoxy­phen­yl)prop-2-en-1-one

In the title compound, C₁₇H₁₅BrO₃, the dihedral angle between the benzene rings is 18.34 (13)°. The crystal structure is stabilized by inter­molecular C—H...O inter­actions and Br...O short contacts.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.129
• Data-to-parameter ratio = 27.5

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:      0.474     0.655
            Tmin(prime) and Tmax expected:      0.531     0.637
            RR(prime) =      0.867
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O3      ..       3.19 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
   1 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

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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).

3-(4-bromophenyl)-1-(2,5-dimethoxyphenyl)prop-2-en-1-one

Crystal data

C17H15BrO3	F(000) = 1408
Mr = 347.20	Dx = 1.576 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8581 reflections
a = 34.1239 (8) Å	θ = 1.2–32.5°
b = 4.6292 (1) Å	µ = 2.82 mm^−1
c = 19.0194 (4) Å	T = 100 K
β = 103.001 (2)°	Block, yellow
V = 2927.41 (11) Å^3	0.22 × 0.16 × 0.16 mm
Z = 8

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	5274 independent reflections
Radiation source: fine-focus sealed tube	3716 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
Detector resolution: 8.33 pixels mm^-1	θmax = 32.5°, θmin = 1.2°
ω scans	h = −48→51
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
Tmin = 0.474, Tmax = 0.655	l = −28→28
46788 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.16	w = 1/[σ^2(Fo^2) + (0.0626P)^2 + 2.8596P] where P = (Fo^2 + 2Fc^2)/3
5274 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.60 e Å^−3
0 restraints	Δρmin = −1.01 e Å^−3

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.209883 (7)	0.13524 (6)	0.112998 (13)	0.02202 (9)
O1	0.39516 (6)	0.7559 (5)	0.22725 (10)	0.0230 (4)
O2	0.48667 (6)	1.4259 (5)	0.15190 (11)	0.0261 (4)
O3	0.37138 (6)	1.7272 (5)	−0.09129 (11)	0.0256 (4)
C1	0.30538 (8)	0.6467 (5)	0.08658 (14)	0.0187 (5)
H1A	0.3126	0.7457	0.0488	0.022*
C2	0.26938 (8)	0.4925 (6)	0.07401 (14)	0.0195 (5)
H2A	0.2525	0.4886	0.0282	0.023*
C3	0.25897 (7)	0.3447 (6)	0.13061 (14)	0.0187 (5)
C4	0.28354 (8)	0.3484 (6)	0.19946 (14)	0.0205 (5)
H4A	0.2762	0.2491	0.2370	0.025*
C5	0.31942 (8)	0.5037 (6)	0.21123 (14)	0.0195 (5)
H5A	0.3361	0.5073	0.2572	0.023*
C6	0.33068 (7)	0.6539 (5)	0.15532 (13)	0.0163 (4)
C7	0.37016 (8)	0.8110 (5)	0.17147 (14)	0.0180 (5)
C8	0.37744 (7)	1.0273 (5)	0.11946 (14)	0.0185 (5)
H8A	0.3567	1.0728	0.0802	0.022*
C9	0.41279 (7)	1.1615 (5)	0.12634 (13)	0.0178 (5)
H9A	0.4332	1.1133	0.1659	0.021*
C10	0.42190 (7)	1.3785 (5)	0.07635 (13)	0.0171 (4)
C11	0.46002 (8)	1.5121 (6)	0.09056 (14)	0.0205 (5)
C12	0.46840 (8)	1.7177 (7)	0.04275 (15)	0.0244 (5)
H12A	0.4935	1.8059	0.0521	0.029*
C13	0.43967 (8)	1.7940 (6)	−0.01914 (15)	0.0225 (5)
H13A	0.4458	1.9306	−0.0509	0.027*
C14	0.40216 (8)	1.6657 (6)	−0.03299 (14)	0.0195 (5)
C15	0.39370 (8)	1.4586 (6)	0.01446 (14)	0.0196 (5)
H15A	0.3685	1.3712	0.0046	0.024*
C16	0.37963 (9)	1.9302 (6)	−0.14269 (15)	0.0246 (5)
H16A	0.3560	1.9561	−0.1805	0.037*
H16B	0.4012	1.8591	−0.1628	0.037*
H16C	0.3873	2.1119	−0.1193	0.037*
C17	0.52292 (8)	1.5917 (7)	0.17446 (17)	0.0296 (6)
H17A	0.5380	1.5195	0.2198	0.044*
H17B	0.5162	1.7907	0.1797	0.044*
H17C	0.5388	1.5758	0.1389	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01411 (13)	0.03246 (16)	0.02112 (13)	−0.00546 (10)	0.00740 (9)	0.00024 (10)
O1	0.0162 (9)	0.0313 (10)	0.0213 (9)	−0.0011 (8)	0.0038 (7)	0.0007 (8)
O2	0.0144 (9)	0.0345 (11)	0.0271 (10)	−0.0066 (8)	−0.0001 (7)	0.0034 (8)
O3	0.0199 (9)	0.0299 (10)	0.0254 (9)	−0.0059 (8)	0.0015 (7)	0.0064 (8)
C1	0.0168 (11)	0.0220 (12)	0.0189 (11)	−0.0010 (9)	0.0072 (9)	0.0019 (9)
C2	0.0151 (11)	0.0243 (13)	0.0203 (11)	−0.0011 (9)	0.0063 (9)	0.0019 (9)
C3	0.0133 (10)	0.0232 (12)	0.0222 (11)	−0.0020 (9)	0.0094 (9)	−0.0024 (9)
C4	0.0180 (11)	0.0266 (13)	0.0186 (11)	−0.0011 (10)	0.0075 (9)	0.0021 (9)
C5	0.0169 (11)	0.0240 (13)	0.0180 (11)	−0.0020 (9)	0.0046 (9)	0.0001 (9)
C6	0.0122 (10)	0.0173 (11)	0.0206 (11)	0.0008 (8)	0.0064 (8)	−0.0002 (8)
C7	0.0139 (11)	0.0208 (12)	0.0196 (11)	−0.0002 (8)	0.0044 (9)	−0.0031 (9)
C8	0.0137 (11)	0.0193 (11)	0.0227 (11)	0.0004 (9)	0.0045 (9)	−0.0006 (9)
C9	0.0146 (11)	0.0215 (12)	0.0181 (10)	0.0003 (9)	0.0055 (8)	−0.0017 (9)
C10	0.0129 (10)	0.0184 (11)	0.0210 (10)	−0.0004 (9)	0.0062 (8)	−0.0031 (9)
C11	0.0134 (11)	0.0251 (13)	0.0234 (12)	−0.0015 (9)	0.0052 (9)	−0.0019 (10)
C12	0.0147 (12)	0.0310 (14)	0.0286 (13)	−0.0063 (10)	0.0071 (10)	0.0005 (11)
C13	0.0188 (12)	0.0261 (13)	0.0244 (12)	−0.0051 (10)	0.0087 (10)	0.0012 (10)
C14	0.0158 (11)	0.0224 (12)	0.0213 (11)	−0.0020 (9)	0.0063 (9)	−0.0011 (9)
C15	0.0139 (11)	0.0215 (11)	0.0238 (12)	−0.0022 (9)	0.0051 (9)	−0.0016 (9)
C16	0.0258 (14)	0.0268 (14)	0.0216 (12)	−0.0025 (10)	0.0061 (10)	0.0032 (10)
C17	0.0146 (12)	0.0421 (17)	0.0306 (14)	−0.0087 (11)	0.0016 (10)	−0.0003 (12)

Geometric parameters (Å, º)

Br1—C3	1.899 (2)	C8—H8A	0.9300
O1—C7	1.229 (3)	C9—C10	1.464 (4)
O2—C11	1.367 (3)	C9—H9A	0.9300
O2—C17	1.437 (3)	C10—C15	1.393 (4)
O3—C14	1.375 (3)	C10—C11	1.410 (3)
O3—C16	1.429 (3)	C11—C12	1.390 (4)
C1—C2	1.394 (4)	C12—C13	1.397 (4)
C1—C6	1.396 (3)	C12—H12A	0.9300
C1—H1A	0.9300	C13—C14	1.381 (4)
C2—C3	1.387 (4)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.391 (4)
C3—C4	1.387 (4)	C15—H15A	0.9300
C4—C5	1.394 (4)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.395 (3)	C16—H16C	0.9600
C5—H5A	0.9300	C17—H17A	0.9600
C6—C7	1.500 (3)	C17—H17B	0.9600
C7—C8	1.468 (4)	C17—H17C	0.9600
C8—C9	1.337 (3)
C11—O2—C17	117.5 (2)	C15—C10—C9	121.6 (2)
C14—O3—C16	117.1 (2)	C11—C10—C9	119.9 (2)
C2—C1—C6	120.6 (2)	O2—C11—C12	124.2 (2)
C2—C1—H1A	119.7	O2—C11—C10	116.3 (2)
C6—C1—H1A	119.7	C12—C11—C10	119.5 (2)
C3—C2—C1	119.3 (2)	C11—C12—C13	121.0 (2)
C3—C2—H2A	120.4	C11—C12—H12A	119.5
C1—C2—H2A	120.4	C13—C12—H12A	119.5
C4—C3—C2	121.4 (2)	C14—C13—C12	119.8 (3)
C4—C3—Br1	119.64 (19)	C14—C13—H13A	120.1
C2—C3—Br1	118.98 (19)	C12—C13—H13A	120.1
C3—C4—C5	118.7 (2)	O3—C14—C13	124.9 (2)
C3—C4—H4A	120.6	O3—C14—C15	115.7 (2)
C5—C4—H4A	120.6	C13—C14—C15	119.4 (2)
C4—C5—C6	121.2 (2)	C14—C15—C10	121.8 (2)
C4—C5—H5A	119.4	C14—C15—H15A	119.1
C6—C5—H5A	119.4	C10—C15—H15A	119.1
C5—C6—C1	118.9 (2)	O3—C16—H16A	109.5
C5—C6—C7	118.3 (2)	O3—C16—H16B	109.5
C1—C6—C7	122.8 (2)	H16A—C16—H16B	109.5
O1—C7—C8	122.2 (2)	O3—C16—H16C	109.5
O1—C7—C6	119.5 (2)	H16A—C16—H16C	109.5
C8—C7—C6	118.2 (2)	H16B—C16—H16C	109.5
C9—C8—C7	122.5 (2)	O2—C17—H17A	109.5
C9—C8—H8A	118.8	O2—C17—H17B	109.5
C7—C8—H8A	118.8	H17A—C17—H17B	109.5
C8—C9—C10	125.0 (2)	O2—C17—H17C	109.5
C8—C9—H9A	117.5	H17A—C17—H17C	109.5
C10—C9—H9A	117.5	H17B—C17—H17C	109.5
C15—C10—C11	118.5 (2)
C6—C1—C2—C3	−0.2 (4)	C8—C9—C10—C11	178.0 (3)
C1—C2—C3—C4	0.3 (4)	C17—O2—C11—C12	10.8 (4)
C1—C2—C3—Br1	179.99 (19)	C17—O2—C11—C10	−169.5 (2)
C2—C3—C4—C5	−0.2 (4)	C15—C10—C11—O2	−179.9 (2)
Br1—C3—C4—C5	−179.94 (19)	C9—C10—C11—O2	0.2 (4)
C3—C4—C5—C6	0.1 (4)	C15—C10—C11—C12	−0.2 (4)
C4—C5—C6—C1	−0.1 (4)	C9—C10—C11—C12	180.0 (2)
C4—C5—C6—C7	−178.6 (2)	O2—C11—C12—C13	179.7 (3)
C2—C1—C6—C5	0.1 (4)	C10—C11—C12—C13	0.0 (4)
C2—C1—C6—C7	178.6 (2)	C11—C12—C13—C14	0.6 (4)
C5—C6—C7—O1	15.5 (4)	C16—O3—C14—C13	2.8 (4)
C1—C6—C7—O1	−163.0 (2)	C16—O3—C14—C15	−177.5 (2)
C5—C6—C7—C8	−164.4 (2)	C12—C13—C14—O3	178.8 (3)
C1—C6—C7—C8	17.1 (4)	C12—C13—C14—C15	−0.9 (4)
O1—C7—C8—C9	5.5 (4)	O3—C14—C15—C10	−179.0 (2)
C6—C7—C8—C9	−174.6 (2)	C13—C14—C15—C10	0.8 (4)
C7—C8—C9—C10	179.9 (2)	C11—C10—C15—C14	−0.2 (4)
C8—C9—C10—C15	−1.9 (4)	C9—C10—C15—C14	179.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2	0.93	2.39	2.746 (3)	103
C17—H17A···O1^i	0.96	2.53	3.088 (4)	118

Symmetry code: (i) −x+1, y+1, −z+1/2.