(2E)-3-(Biphenyl-4-yl)-1-(4-bromo­phen­yl)prop-2-en-1-one

The title compound, C₂₁H₁₅BrO, was obtained from 4-bromo­acetophenone and biphenyl-4-carbaldehyde. The geometry of the mol­ecule is unexceptional. The compound crystallizes isostructurally with the corresponding chloro compound.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.016 Å
• R factor = 0.064
• wR factor = 0.158
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         16

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96

Alert level G
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           25.50
           From the CIF: _reflns_number_total               2434
           Count of symmetry unique reflns         1565
           Completeness (_total/calc)            155.53%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       869
           Fraction of Friedel pairs measured     0.555
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).

(2E)-3-(Biphenyl-4-yl)-1-(4-bromophenyl)prop-2-en-1-one

Crystal data

C21H15BrO	F(000) = 736
Mr = 363.26	Dx = 1.440 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 21 reflections
a = 37.35 (3) Å	θ = 4.7–12.4°
b = 7.3663 (15) Å	µ = 2.45 mm^−1
c = 6.0978 (17) Å	T = 296 K
β = 92.63 (4)°	Plate, light yellow
V = 1675.9 (15) Å^3	0.44 × 0.23 × 0.05 mm
Z = 4

Data collection

Bruker–Nonius KappaCCD diffractometer	1640 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.075
ω scans	θmax = 25.5°, θmin = 4.6°
Absorption correction: numerical (Herrendorf & Bärnighausen, 1997)	h = −44→39
Tmin = 0.530, Tmax = 0.864	k = −8→7
4893 measured reflections	l = −7→6
2434 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.064	w = 1/[σ^2(Fo^2) + (0.0299P)^2 + 8.9572P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.158	(Δ/σ)max < 0.001
S = 1.17	Δρmax = 0.24 e Å^−3
2434 reflections	Δρmin = −0.34 e Å^−3
208 parameters	Absolute structure: Flack (1983), 924 Friedel pairs
2 restraints	Absolute structure parameter: −0.01 (3)
Primary atom site location: structure-invariant direct methods

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
C1	0.6912 (3)	0.7737 (14)	0.3586 (17)	0.063 (3)
C2	0.6610 (3)	0.8290 (14)	0.4609 (15)	0.059 (3)
H2	0.6628	0.8809	0.6000	0.070*
C3	0.6278 (3)	0.8055 (15)	0.3515 (15)	0.061 (3)
H3	0.6071	0.8397	0.4206	0.073*
C4	0.6247 (3)	0.7319 (14)	0.1402 (18)	0.057 (3)
C5	0.6560 (3)	0.6811 (14)	0.038 (2)	0.058 (3)
H5	0.6545	0.6367	−0.1051	0.070*
C6	0.6894 (3)	0.6967 (15)	0.1480 (16)	0.062 (3)
H6	0.7101	0.6568	0.0833	0.074*
C7	0.5889 (3)	0.7184 (18)	0.019 (2)	0.066 (3)
C8	0.5557 (3)	0.7156 (15)	0.1387 (19)	0.058 (3)
H8	0.5567	0.6840	0.2865	0.069*
C9	0.5245 (4)	0.7569 (16)	0.041 (2)	0.058 (3)
H9	0.5253	0.7897	−0.1057	0.070*
C10	0.4891 (3)	0.7585 (15)	0.1299 (18)	0.050 (3)
C11	0.4819 (4)	0.6834 (15)	0.336 (2)	0.057 (4)
H11	0.5007	0.6338	0.4209	0.069*
C12	0.4474 (3)	0.6809 (14)	0.4169 (18)	0.051 (3)
H12	0.4439	0.6321	0.5550	0.061*
C13	0.4177 (3)	0.7520 (15)	0.2905 (16)	0.047 (3)
C14	0.4252 (3)	0.8264 (11)	0.0855 (14)	0.052 (2)
H14	0.4064	0.8754	−0.0007	0.062*
C15	0.4593 (3)	0.8297 (13)	0.0068 (14)	0.053 (3)
H15	0.4628	0.8800	−0.1305	0.063*
C16	0.3806 (3)	0.7511 (13)	0.3782 (17)	0.051 (3)
C17	0.3730 (3)	0.6669 (14)	0.5728 (16)	0.053 (3)
H17	0.3915	0.6120	0.6559	0.063*
C18	0.3391 (3)	0.6621 (14)	0.6465 (16)	0.062 (3)
H18	0.3351	0.6040	0.7785	0.074*
C19	0.3103 (4)	0.7422 (15)	0.529 (2)	0.068 (3)
H19	0.2870	0.7347	0.5769	0.082*
C20	0.3177 (3)	0.8332 (14)	0.3377 (19)	0.063 (3)
H20	0.2995	0.8929	0.2582	0.076*
C21	0.3524 (3)	0.8359 (14)	0.2637 (17)	0.056 (3)
H21	0.3568	0.8963	0.1337	0.067*
Br1	0.73698 (5)	0.79797 (17)	0.50629 (19)	0.0925 (5)
O1	0.5885 (2)	0.7059 (12)	−0.1871 (13)	0.086 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.072 (7)	0.046 (7)	0.070 (7)	−0.004 (5)	0.003 (6)	0.006 (5)
C2	0.071 (7)	0.054 (7)	0.051 (6)	−0.002 (5)	0.013 (5)	−0.009 (5)
C3	0.065 (7)	0.062 (7)	0.057 (6)	0.006 (5)	0.023 (5)	0.007 (5)
C4	0.075 (8)	0.042 (6)	0.054 (7)	0.000 (5)	0.015 (6)	0.006 (5)
C5	0.080 (9)	0.047 (7)	0.048 (7)	0.004 (6)	0.003 (7)	0.009 (5)
C6	0.068 (7)	0.048 (6)	0.071 (7)	0.008 (6)	0.011 (5)	0.004 (6)
C7	0.066 (8)	0.066 (8)	0.068 (9)	0.000 (6)	0.018 (7)	0.015 (7)
C8	0.058 (7)	0.062 (8)	0.054 (7)	−0.004 (6)	0.008 (6)	0.004 (6)
C9	0.072 (8)	0.046 (6)	0.057 (7)	−0.008 (6)	0.007 (6)	−0.006 (5)
C10	0.066 (7)	0.040 (6)	0.046 (7)	−0.004 (5)	0.013 (5)	0.005 (5)
C11	0.065 (8)	0.046 (8)	0.060 (8)	0.009 (5)	−0.009 (6)	−0.004 (5)
C12	0.061 (7)	0.045 (7)	0.046 (6)	0.002 (5)	0.006 (5)	0.015 (5)
C13	0.062 (7)	0.037 (5)	0.041 (6)	−0.001 (4)	−0.002 (5)	−0.008 (5)
C14	0.070 (7)	0.036 (6)	0.049 (6)	−0.003 (5)	−0.004 (5)	0.005 (4)
C15	0.058 (6)	0.056 (7)	0.042 (5)	0.004 (5)	−0.004 (5)	0.007 (4)
C16	0.068 (8)	0.031 (6)	0.053 (7)	−0.001 (5)	−0.005 (6)	0.003 (5)
C17	0.049 (6)	0.066 (8)	0.045 (6)	0.004 (5)	0.014 (5)	0.005 (5)
C18	0.088 (8)	0.046 (7)	0.052 (6)	0.005 (5)	0.007 (6)	0.005 (5)
C19	0.081 (8)	0.049 (7)	0.076 (8)	−0.009 (7)	0.020 (7)	−0.012 (7)
C20	0.052 (7)	0.059 (7)	0.077 (8)	0.003 (5)	−0.005 (6)	0.014 (6)
C21	0.068 (7)	0.046 (7)	0.053 (7)	−0.001 (5)	−0.009 (5)	0.005 (5)
Br1	0.0751 (7)	0.1123 (9)	0.0887 (8)	−0.0010 (13)	−0.0107 (5)	−0.0009 (13)
O1	0.075 (5)	0.122 (7)	0.062 (5)	−0.004 (5)	0.010 (4)	−0.005 (5)

Geometric parameters (Å, º)

C1—C2	1.373 (13)	C11—C12	1.400 (19)
C1—C6	1.403 (13)	C11—H11	0.9300
C1—Br1	1.905 (10)	C12—C13	1.422 (18)
C2—C3	1.394 (13)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.404 (13)
C3—C4	1.397 (14)	C13—C16	1.509 (16)
C3—H3	0.9300	C14—C15	1.382 (13)
C4—C5	1.402 (17)	C14—H14	0.9300
C4—C7	1.501 (16)	C15—H15	0.9300
C5—C6	1.394 (15)	C16—C17	1.380 (14)
C5—H5	0.9300	C16—C21	1.385 (14)
C6—H6	0.9300	C17—C18	1.362 (13)
C7—O1	1.261 (13)	C17—H17	0.9300
C7—C8	1.466 (17)	C18—C19	1.398 (15)
C8—C9	1.321 (19)	C18—H18	0.9300
C8—H8	0.9300	C19—C20	1.384 (15)
C9—C10	1.45 (2)	C19—H19	0.9300
C9—H9	0.9300	C20—C21	1.392 (15)
C10—C11	1.409 (12)	C20—H20	0.9300
C10—C15	1.413 (15)	C21—H21	0.9300
C2—C1—C6	122.1 (10)	C10—C11—H11	118.8
C2—C1—Br1	119.6 (8)	C11—C12—C13	120.7 (11)
C6—C1—Br1	118.3 (8)	C11—C12—H12	119.7
C1—C2—C3	118.5 (9)	C13—C12—H12	119.7
C1—C2—H2	120.8	C14—C13—C12	116.4 (11)
C3—C2—H2	120.8	C14—C13—C16	122.8 (10)
C2—C3—C4	121.5 (9)	C12—C13—C16	120.9 (10)
C2—C3—H3	119.2	C15—C14—C13	122.7 (9)
C4—C3—H3	119.2	C15—C14—H14	118.6
C3—C4—C5	118.7 (11)	C13—C14—H14	118.6
C3—C4—C7	120.8 (10)	C14—C15—C10	121.6 (9)
C5—C4—C7	120.4 (10)	C14—C15—H15	119.2
C6—C5—C4	120.6 (11)	C10—C15—H15	119.2
C6—C5—H5	119.7	C17—C16—C21	117.1 (11)
C4—C5—H5	119.7	C17—C16—C13	122.4 (10)
C5—C6—C1	118.5 (10)	C21—C16—C13	120.5 (10)
C5—C6—H6	120.7	C18—C17—C16	121.8 (10)
C1—C6—H6	120.7	C18—C17—H17	119.1
O1—C7—C8	121.6 (11)	C16—C17—H17	119.1
O1—C7—C4	117.7 (10)	C17—C18—C19	121.7 (10)
C8—C7—C4	120.8 (11)	C17—C18—H18	119.1
C9—C8—C7	121.5 (12)	C19—C18—H18	119.1
C9—C8—H8	119.2	C20—C19—C18	117.1 (12)
C7—C8—H8	119.2	C20—C19—H19	121.4
C8—C9—C10	129.5 (13)	C18—C19—H19	121.4
C8—C9—H9	115.3	C19—C20—C21	120.5 (11)
C10—C9—H9	115.3	C19—C20—H20	119.8
C11—C10—C15	116.3 (9)	C21—C20—H20	119.8
C11—C10—C9	122.8 (10)	C16—C21—C20	121.8 (11)
C15—C10—C9	120.9 (11)	C16—C21—H21	119.1
C12—C11—C10	122.4 (9)	C20—C21—H21	119.1
C12—C11—H11	118.8