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

The title compound, C₁₅H₁₀BrNO₃, is close to planar, as seen by the dihedral angle of 3.32 (17)° between the bromo­phenyl and nitro­phenyl rings. In the crystal, mol­ecules are linked by weak C—H...O hydrogen bonds, forming chains propagating along the c-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.033
• wR factor = 0.083
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     --  N1      ..        7.0 s.u.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Note

   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
   3 ALERT level G = General information/check it is not something unexpected

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: CrystalClear SM-Expert (Rigaku, 2011); cell refinement: CrystalClear SM-Expert (Rigaku, 2011); data reduction: CrystalClear SM-Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

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

Crystal data

C15H10BrNO3	F(000) = 332
Mr = 332.14	Dx = 1.660 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2325 reflections
a = 6.0511 (7) Å	θ = 1.9–26.1°
b = 5.0542 (6) Å	µ = 3.10 mm^−1
c = 21.841 (3) Å	T = 294 K
β = 95.781 (2)°	Rectangle, brown
V = 664.58 (14) Å^3	0.49 × 0.28 × 0.10 mm
Z = 2

Data collection

Rigaku Saturn724+ diffractometer	2605 independent reflections
Radiation source: fine-focus sealed tube	2325 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 18.4 pixels mm^-1	θmax = 26.1°, θmin = 1.9°
profile data from ω–scans	h = −7→7
Absorption correction: multi-scan (NUMABS; Rigaku, 1999)	k = −6→6
Tmin = 0.312, Tmax = 0.751	l = −27→24
8418 measured reflections

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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0421P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2605 reflections	Δρmax = 0.59 e Å^−3
181 parameters	Δρmin = −0.40 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.028 (11)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	0.10940 (5)	1.49979 (11)	0.55889 (2)	0.0536 (1)
O1	0.1299 (4)	0.7918 (8)	0.74119 (13)	0.0805 (13)
O2	0.8278 (4)	−0.4766 (7)	0.98538 (11)	0.0523 (8)
O3	1.0879 (4)	−0.4357 (5)	0.92554 (12)	0.0544 (10)
N1	0.9084 (4)	−0.3727 (6)	0.94205 (13)	0.0397 (9)
C1	0.5966 (6)	0.8764 (8)	0.65218 (17)	0.0499 (11)
C2	0.6499 (5)	1.0205 (12)	0.60163 (17)	0.0576 (13)
C3	0.5076 (6)	1.1998 (8)	0.57345 (18)	0.0522 (12)
C4	0.3066 (5)	1.2470 (7)	0.59803 (15)	0.0405 (11)
C5	0.2521 (6)	1.1097 (7)	0.64856 (17)	0.0401 (11)
C6	0.3956 (5)	0.9202 (6)	0.67594 (16)	0.0384 (11)
C7	0.3196 (6)	0.7626 (8)	0.72774 (16)	0.0461 (12)
C8	0.4693 (6)	0.5698 (7)	0.76037 (16)	0.0470 (14)
C9	0.4138 (6)	0.4312 (7)	0.80724 (17)	0.0435 (13)
C10	0.5470 (5)	0.2282 (7)	0.84194 (15)	0.0359 (10)
C11	0.4689 (5)	0.1157 (7)	0.89396 (16)	0.0409 (10)
C12	0.5857 (5)	−0.0774 (6)	0.92742 (17)	0.0375 (11)
C13	0.7850 (5)	−0.1623 (6)	0.90817 (15)	0.0326 (10)
C14	0.8681 (5)	−0.0549 (7)	0.85751 (16)	0.0421 (13)
C15	0.7494 (6)	0.1405 (7)	0.82458 (16)	0.0434 (11)
H1A	0.69530	0.75090	0.67010	0.0600*
H2A	0.78680	0.99340	0.58670	0.0690*
H3A	0.54270	1.28940	0.53850	0.0630*
H5A	0.11820	1.14370	0.66450	0.0480*
H8A	0.60940	0.54470	0.74730	0.0560*
H9A	0.27440	0.46550	0.81990	0.0530*
H11A	0.33430	0.17310	0.90630	0.0490*
H12A	0.53230	−0.14960	0.96220	0.0450*
H14A	1.00300	−0.11330	0.84550	0.0510*
H15A	0.80550	0.21450	0.79040	0.0520*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0622 (2)	0.0424 (2)	0.0541 (2)	0.0079 (2)	−0.0041 (2)	0.0068 (2)
O1	0.0605 (17)	0.120 (3)	0.066 (2)	0.0404 (18)	0.0305 (15)	0.0444 (19)
O2	0.0533 (12)	0.0489 (16)	0.0559 (14)	0.0060 (14)	0.0111 (10)	0.0179 (16)
O3	0.0488 (13)	0.052 (2)	0.0643 (17)	0.0202 (11)	0.0158 (12)	0.0045 (12)
N1	0.0420 (16)	0.0328 (15)	0.0434 (18)	0.0072 (11)	−0.0004 (13)	−0.0078 (12)
C1	0.0431 (18)	0.054 (2)	0.052 (2)	0.0101 (16)	0.0022 (17)	0.0085 (17)
C2	0.0443 (17)	0.065 (3)	0.066 (2)	0.006 (2)	0.0182 (15)	0.016 (3)
C3	0.051 (2)	0.054 (2)	0.053 (2)	−0.0019 (19)	0.0127 (17)	0.0123 (19)
C4	0.0490 (19)	0.0328 (18)	0.0381 (19)	0.0016 (14)	−0.0038 (15)	0.0002 (14)
C5	0.0385 (17)	0.0447 (19)	0.037 (2)	0.0058 (14)	0.0032 (15)	−0.0062 (14)
C6	0.0427 (18)	0.040 (2)	0.0321 (18)	0.0037 (13)	0.0024 (14)	−0.0023 (12)
C7	0.049 (2)	0.052 (2)	0.037 (2)	0.0157 (17)	0.0036 (16)	−0.0008 (16)
C8	0.0482 (19)	0.053 (3)	0.041 (2)	0.0103 (16)	0.0100 (16)	0.0053 (15)
C9	0.0398 (16)	0.049 (3)	0.042 (2)	0.0085 (14)	0.0052 (15)	−0.0002 (14)
C10	0.0390 (16)	0.0366 (18)	0.0328 (18)	0.0010 (14)	0.0065 (13)	0.0016 (13)
C11	0.0342 (16)	0.0449 (18)	0.045 (2)	0.0069 (14)	0.0108 (15)	0.0003 (15)
C12	0.0398 (16)	0.034 (2)	0.0403 (19)	0.0021 (12)	0.0120 (14)	0.0030 (12)
C13	0.0336 (15)	0.0270 (17)	0.0370 (18)	0.0019 (12)	0.0027 (13)	0.0000 (13)
C14	0.0339 (15)	0.050 (3)	0.044 (2)	0.0070 (14)	0.0117 (14)	−0.0025 (15)
C15	0.0463 (19)	0.047 (2)	0.039 (2)	0.0014 (15)	0.0140 (16)	0.0061 (16)

Geometric parameters (Å, º)

Br1—C4	1.893 (3)	C10—C15	1.391 (5)
O1—C7	1.222 (4)	C11—C12	1.372 (5)
O2—N1	1.226 (4)	C12—C13	1.385 (4)
O3—N1	1.221 (4)	C13—C14	1.373 (5)
N1—C13	1.458 (4)	C14—C15	1.380 (5)
C1—C2	1.388 (6)	C1—H1A	0.9300
C1—C6	1.387 (5)	C2—H2A	0.9300
C2—C3	1.355 (6)	C3—H3A	0.9300
C3—C4	1.399 (5)	C5—H5A	0.9300
C4—C5	1.372 (5)	C8—H8A	0.9300
C5—C6	1.387 (5)	C9—H9A	0.9300
C6—C7	1.494 (5)	C11—H11A	0.9300
C7—C8	1.466 (5)	C12—H12A	0.9300
C8—C9	1.312 (5)	C14—H14A	0.9300
C9—C10	1.468 (5)	C15—H15A	0.9300
C10—C11	1.395 (5)
O2—N1—O3	123.5 (3)	N1—C13—C14	119.2 (3)
O2—N1—C13	118.8 (3)	C12—C13—C14	121.6 (3)
O3—N1—C13	117.8 (3)	C13—C14—C15	119.3 (3)
C2—C1—C6	119.8 (3)	C10—C15—C14	120.8 (3)
C1—C2—C3	121.7 (3)	C2—C1—H1A	120.00
C2—C3—C4	118.5 (3)	C6—C1—H1A	120.00
Br1—C4—C3	118.4 (3)	C1—C2—H2A	119.00
Br1—C4—C5	120.9 (2)	C3—C2—H2A	119.00
C3—C4—C5	120.8 (3)	C2—C3—H3A	121.00
C4—C5—C6	120.4 (3)	C4—C3—H3A	121.00
C1—C6—C5	118.9 (3)	C4—C5—H5A	120.00
C1—C6—C7	123.1 (3)	C6—C5—H5A	120.00
C5—C6—C7	117.9 (3)	C7—C8—H8A	119.00
O1—C7—C6	119.1 (3)	C9—C8—H8A	119.00
O1—C7—C8	120.9 (4)	C8—C9—H9A	116.00
C6—C7—C8	120.0 (3)	C10—C9—H9A	116.00
C7—C8—C9	122.7 (3)	C10—C11—H11A	119.00
C8—C9—C10	127.3 (3)	C12—C11—H11A	119.00
C9—C10—C11	119.5 (3)	C11—C12—H12A	121.00
C9—C10—C15	122.4 (3)	C13—C12—H12A	121.00
C11—C10—C15	118.2 (3)	C13—C14—H14A	120.00
C10—C11—C12	121.7 (3)	C15—C14—H14A	120.00
C11—C12—C13	118.5 (3)	C10—C15—H15A	120.00
N1—C13—C12	119.3 (3)	C14—C15—H15A	120.00
O2—N1—C13—C12	2.9 (5)	C5—C6—C7—C8	−176.8 (3)
O2—N1—C13—C14	−176.4 (3)	O1—C7—C8—C9	−3.9 (6)
O3—N1—C13—C12	−177.0 (3)	C6—C7—C8—C9	178.1 (3)
O3—N1—C13—C14	3.7 (4)	C7—C8—C9—C10	178.0 (3)
C6—C1—C2—C3	−1.8 (7)	C8—C9—C10—C11	174.7 (4)
C2—C1—C6—C5	−0.4 (6)	C8—C9—C10—C15	−5.9 (6)
C2—C1—C6—C7	176.2 (4)	C9—C10—C11—C12	179.1 (3)
C1—C2—C3—C4	2.8 (7)	C15—C10—C11—C12	−0.4 (5)
C2—C3—C4—Br1	179.5 (3)	C9—C10—C15—C14	−178.6 (3)
C2—C3—C4—C5	−1.7 (6)	C11—C10—C15—C14	0.8 (5)
Br1—C4—C5—C6	178.4 (3)	C10—C11—C12—C13	−0.6 (5)
C3—C4—C5—C6	−0.4 (5)	C11—C12—C13—N1	−178.2 (3)
C4—C5—C6—C1	1.4 (5)	C11—C12—C13—C14	1.1 (5)
C4—C5—C6—C7	−175.4 (3)	N1—C13—C14—C15	178.7 (3)
C1—C6—C7—O1	−171.4 (4)	C12—C13—C14—C15	−0.6 (5)
C1—C6—C7—C8	6.6 (5)	C13—C14—C15—C10	−0.3 (5)
C5—C6—C7—O1	5.2 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O3^i	0.93	2.54	3.354 (4)	147
C14—H14A···O1^ii	0.93	2.52	3.221 (4)	132

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