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

In the title compound, C₁₅H₉BrCl₂O, the mol­ecules form chains along the b axis through short Br...Cl contacts. These chains form layers through C—H...O inter­molecular inter­actions and these layers stack parallel to the c axis.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.050
• wR factor = 0.131
• Data-to-parameter ratio = 22.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.91
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Cl1     ..       3.42 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.913
            Tmax scaled      0.470 Tmin scaled      0.259
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total               3923
           Count of symmetry unique reflns         2351
           Completeness (_total/calc)            166.87%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1572
           Fraction of Friedel pairs measured     0.669
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 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
   1 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 (Bruker, 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).

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

Crystal data

C15H9BrCl2O	F(000) = 704
Mr = 356.03	Dx = 1.756 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8196 reflections
a = 11.4642 (4) Å	θ = 1.4–30.0°
b = 30.0972 (10) Å	µ = 3.44 mm^−1
c = 3.9020 (1) Å	T = 100 K
V = 1346.35 (7) Å^3	Block, yellow
Z = 4	0.51 × 0.29 × 0.22 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3923 independent reflections
Radiation source: fine-focus sealed tube	3809 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 1.4°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −42→42
Tmin = 0.284, Tmax = 0.515	l = −5→5
30878 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)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.0456P)^2 + 5.363P] where P = (Fo^2 + 2Fc^2)/3
S = 1.20	(Δ/σ)max = 0.001
3923 reflections	Δρmax = 1.74 e Å^−3
172 parameters	Δρmin = −1.16 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1572 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.068 (14)

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	0.85416 (4)	0.398731 (15)	−0.70729 (12)	0.02235 (12)
Cl1	1.09004 (12)	−0.00326 (4)	0.6186 (4)	0.0280 (3)
Cl2	0.66526 (10)	0.07008 (4)	0.5591 (4)	0.0243 (2)
O1	0.6195 (3)	0.20630 (12)	−0.0942 (11)	0.0252 (8)
C1	0.8175 (4)	0.34168 (15)	−0.5337 (13)	0.0199 (9)
C2	0.7035 (4)	0.32592 (16)	−0.5653 (14)	0.0212 (9)
H2A	0.6467	0.3430	−0.6727	0.025*
C3	0.6763 (4)	0.28468 (16)	−0.4353 (13)	0.0186 (8)
H3A	0.6006	0.2739	−0.4575	0.022*
C4	0.7603 (3)	0.25865 (14)	−0.2704 (12)	0.0160 (8)
C5	0.8745 (3)	0.27525 (15)	−0.2412 (13)	0.0192 (8)
H5A	0.9314	0.2582	−0.1334	0.023*
C6	0.9034 (4)	0.31660 (15)	−0.3708 (12)	0.0190 (9)
H6A	0.9789	0.3275	−0.3496	0.023*
C7	0.7241 (4)	0.21503 (15)	−0.1211 (12)	0.0175 (8)
C8	0.8126 (4)	0.18321 (15)	−0.0025 (14)	0.0199 (9)
H8A	0.8913	0.1889	−0.0401	0.024*
C9	0.7801 (4)	0.14616 (15)	0.1591 (14)	0.0190 (9)
H9A	0.7009	0.1430	0.2046	0.023*
C10	0.8560 (4)	0.10998 (13)	0.2720 (12)	0.0185 (8)
C11	0.9762 (4)	0.10987 (14)	0.2081 (14)	0.0197 (8)
H11A	1.0088	0.1340	0.0937	0.024*
C12	1.0484 (4)	0.07534 (16)	0.3086 (15)	0.0220 (9)
H12A	1.1279	0.0764	0.2620	0.026*
C13	1.0011 (4)	0.03940 (15)	0.4784 (14)	0.0206 (9)
C14	0.8819 (4)	0.03792 (15)	0.5537 (13)	0.0199 (9)
H14A	0.8501	0.0138	0.6693	0.024*
C15	0.8126 (4)	0.07296 (15)	0.4530 (13)	0.0185 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0276 (2)	0.02075 (19)	0.0187 (2)	−0.00100 (17)	−0.00104 (18)	0.00330 (17)
Cl1	0.0329 (6)	0.0231 (5)	0.0281 (7)	0.0100 (5)	−0.0035 (5)	−0.0006 (5)
Cl2	0.0184 (5)	0.0257 (5)	0.0289 (6)	−0.0040 (4)	0.0041 (4)	0.0020 (5)
O1	0.0131 (14)	0.0297 (17)	0.033 (2)	−0.0018 (12)	0.0036 (13)	0.0037 (16)
C1	0.022 (2)	0.0183 (19)	0.020 (2)	0.0018 (16)	0.0021 (17)	0.0001 (17)
C2	0.021 (2)	0.025 (2)	0.017 (2)	0.0045 (17)	−0.0041 (17)	0.0022 (18)
C3	0.0169 (19)	0.024 (2)	0.015 (2)	0.0050 (15)	−0.0050 (16)	−0.0019 (17)
C4	0.0142 (16)	0.0205 (18)	0.013 (2)	0.0016 (14)	0.0004 (15)	0.0018 (17)
C5	0.0120 (16)	0.0229 (18)	0.023 (2)	0.0027 (14)	0.0004 (16)	0.0016 (18)
C6	0.0177 (18)	0.021 (2)	0.018 (2)	0.0005 (16)	0.0021 (16)	0.0002 (17)
C7	0.0160 (18)	0.0205 (19)	0.016 (2)	0.0011 (15)	0.0032 (15)	0.0011 (16)
C8	0.0141 (18)	0.022 (2)	0.024 (2)	0.0021 (15)	0.0042 (16)	0.0037 (18)
C9	0.0144 (17)	0.0196 (19)	0.023 (2)	−0.0002 (14)	0.0009 (16)	0.0015 (17)
C10	0.0184 (17)	0.0165 (16)	0.021 (2)	−0.0003 (14)	−0.0038 (19)	−0.0004 (15)
C11	0.0206 (19)	0.0201 (19)	0.018 (2)	0.0005 (15)	0.0026 (17)	0.0013 (17)
C12	0.0151 (18)	0.027 (2)	0.024 (2)	0.0017 (15)	0.0012 (18)	−0.003 (2)
C13	0.022 (2)	0.020 (2)	0.020 (2)	0.0056 (16)	0.0019 (17)	−0.0022 (17)
C14	0.026 (2)	0.0196 (19)	0.014 (2)	−0.0006 (16)	−0.0018 (17)	−0.0021 (17)
C15	0.0194 (19)	0.0175 (19)	0.018 (2)	−0.0021 (15)	−0.0006 (17)	−0.0021 (17)

Geometric parameters (Å, º)

Br1—C1	1.893 (5)	C7—C8	1.470 (6)
Cl1—C13	1.728 (5)	C8—C9	1.334 (7)
Cl2—C15	1.741 (5)	C8—H8A	0.9300
O1—C7	1.232 (5)	C9—C10	1.462 (6)
C1—C6	1.394 (7)	C9—H9A	0.9300
C1—C2	1.396 (7)	C10—C11	1.400 (6)
C2—C3	1.377 (7)	C10—C15	1.410 (6)
C2—H2A	0.9300	C11—C12	1.385 (6)
C3—C4	1.398 (6)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.380 (7)
C4—C5	1.406 (6)	C12—H12A	0.9300
C4—C7	1.495 (6)	C13—C14	1.399 (7)
C5—C6	1.384 (6)	C14—C15	1.378 (6)
C5—H5A	0.9300	C14—H14A	0.9300
C6—H6A	0.9300
C6—C1—C2	121.2 (4)	C7—C8—H8A	120.0
C6—C1—Br1	119.8 (4)	C8—C9—C10	126.8 (4)
C2—C1—Br1	119.0 (4)	C8—C9—H9A	116.6
C3—C2—C1	119.1 (4)	C10—C9—H9A	116.6
C3—C2—H2A	120.5	C11—C10—C15	115.8 (4)
C1—C2—H2A	120.5	C11—C10—C9	122.2 (4)
C2—C3—C4	121.3 (4)	C15—C10—C9	122.0 (4)
C2—C3—H3A	119.4	C12—C11—C10	122.7 (4)
C4—C3—H3A	119.4	C12—C11—H11A	118.7
C3—C4—C5	118.7 (4)	C10—C11—H11A	118.7
C3—C4—C7	118.7 (4)	C13—C12—C11	119.3 (4)
C5—C4—C7	122.6 (4)	C13—C12—H12A	120.4
C6—C5—C4	120.8 (4)	C11—C12—H12A	120.4
C6—C5—H5A	119.6	C12—C13—C14	120.6 (4)
C4—C5—H5A	119.6	C12—C13—Cl1	120.2 (4)
C5—C6—C1	119.0 (4)	C14—C13—Cl1	119.1 (4)
C5—C6—H6A	120.5	C15—C14—C13	118.7 (5)
C1—C6—H6A	120.5	C15—C14—H14A	120.7
O1—C7—C8	120.4 (4)	C13—C14—H14A	120.7
O1—C7—C4	119.4 (4)	C14—C15—C10	123.0 (4)
C8—C7—C4	120.2 (4)	C14—C15—Cl2	117.0 (4)
C9—C8—C7	120.1 (4)	C10—C15—Cl2	120.1 (3)
C9—C8—H8A	120.0
C6—C1—C2—C3	−0.6 (8)	C7—C8—C9—C10	175.6 (5)
Br1—C1—C2—C3	−179.2 (4)	C8—C9—C10—C11	−2.4 (8)
C1—C2—C3—C4	0.6 (8)	C8—C9—C10—C15	177.5 (5)
C2—C3—C4—C5	−0.5 (7)	C15—C10—C11—C12	1.4 (7)
C2—C3—C4—C7	177.4 (5)	C9—C10—C11—C12	−178.8 (5)
C3—C4—C5—C6	0.4 (7)	C10—C11—C12—C13	0.0 (8)
C7—C4—C5—C6	−177.4 (4)	C11—C12—C13—C14	−0.9 (8)
C4—C5—C6—C1	−0.4 (7)	C11—C12—C13—Cl1	−177.9 (4)
C2—C1—C6—C5	0.5 (7)	C12—C13—C14—C15	0.4 (8)
Br1—C1—C6—C5	179.1 (4)	Cl1—C13—C14—C15	177.4 (4)
C3—C4—C7—O1	−12.2 (7)	C13—C14—C15—C10	1.1 (8)
C5—C4—C7—O1	165.5 (5)	C13—C14—C15—Cl2	−178.9 (4)
C3—C4—C7—C8	168.8 (4)	C11—C10—C15—C14	−2.0 (7)
C5—C4—C7—C8	−13.4 (7)	C9—C10—C15—C14	178.2 (5)
O1—C7—C8—C9	−5.1 (8)	C11—C10—C15—Cl2	178.1 (4)
C4—C7—C8—C9	173.8 (5)	C9—C10—C15—Cl2	−1.8 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1^i	0.93	2.57	3.148 (5)	121
C6—H6A···O1^i	0.93	2.58	3.147 (6)	120
C9—H9A···Cl2	0.93	2.63	3.068 (5)	110
C9—H9A···O1	0.93	2.42	2.765 (6)	102

Symmetry code: (i) x+1/2, −y+1/2, −z.