2-(4-Bromo­benzyl)-1,3-di­phenyl­propane-1,3-dione

The title compound, C₂₂H₁₇BrO₂, was obtained from the mono­alkyl­ation reaction of di­benzoyl­methane with 4-bromo-1-(bromo­methyl)­benzene catalyzed by an­hydro­us potassium carbonate in acetone. A 1:1 ratio of dibenzoylmethane to p-bromo­benzyl bromide was utilized to produce this compound.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.031
• wR factor = 0.085
• Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.75
           From the CIF: _reflns_number_total               1874
           Count of symmetry unique reflns         1885
           Completeness (_total/calc)             99.42%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 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
   0 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, 2003); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

2-(4-Bromobenzyl)-1,3-diphenylpropane-1,3-dione

Crystal data

C22H17BrO2	F(000) = 400
Mr = 393.27	Dx = 1.465 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.7227 (13) Å	Cell parameters from 3450 reflections
b = 5.8099 (9) Å	θ = 2.3–23.8°
c = 18.074 (3) Å	µ = 2.32 mm^−1
β = 103.203 (6)°	T = 298 K
V = 891.8 (2) Å^3	Needle, colorless
Z = 2	0.37 × 0.09 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1874 independent reflections
Radiation source: fine-focus sealed tube	1600 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 25.8°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.725, Tmax = 0.869	k = −7→6
7930 measured reflections	l = −21→22

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)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0504P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.029
1874 reflections	Δρmax = 0.29 e Å^−3
226 parameters	Δρmin = −0.37 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.030 (11)

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
C15	−0.2047 (5)	−0.2801 (7)	0.5825 (2)	0.0573 (11)
H15	−0.2203	−0.4180	0.6058	0.069*
Br1	−0.37483 (4)	−0.18089 (13)	0.98083 (2)	0.0813 (2)
O1	0.2821 (3)	−0.1769 (6)	0.65672 (14)	0.0628 (7)
O2	0.0016 (3)	−0.3917 (4)	0.71902 (14)	0.0540 (7)
C2	0.1291 (4)	−0.0264 (6)	0.73798 (18)	0.0371 (7)
H2	0.0815	0.1272	0.7335	0.044*
C3	0.0102 (4)	−0.1997 (6)	0.69373 (17)	0.0386 (7)
C1	0.2705 (4)	−0.0260 (6)	0.70153 (19)	0.0409 (8)
C5	0.3840 (4)	0.3429 (7)	0.7663 (2)	0.0492 (8)
H5	0.2954	0.3630	0.7861	0.059*
C9	0.5299 (4)	0.1285 (7)	0.6929 (2)	0.0477 (9)
H9	0.5403	0.0017	0.6630	0.057*
C4	0.3955 (4)	0.1525 (6)	0.72172 (19)	0.0409 (8)
C8	0.6477 (4)	0.2925 (8)	0.7084 (2)	0.0586 (10)
H8	0.7365	0.2761	0.6885	0.070*
C6	0.5042 (5)	0.5027 (7)	0.7812 (3)	0.0597 (11)
H6	0.4960	0.6299	0.8112	0.072*
C7	0.6347 (4)	0.4769 (7)	0.7524 (3)	0.0581 (10)
H7	0.7148	0.5859	0.7631	0.070*
C10	−0.0899 (4)	−0.1327 (5)	0.61861 (17)	0.0386 (7)
C14	−0.2977 (5)	−0.2284 (8)	0.5122 (2)	0.0721 (14)
H14	−0.3736	−0.3329	0.4881	0.086*
C11	−0.0716 (4)	0.0752 (6)	0.58328 (19)	0.0458 (9)
H11	0.0035	0.1807	0.6073	0.055*
C12	−0.1648 (5)	0.1245 (7)	0.5127 (2)	0.0582 (10)
H12	−0.1495	0.2612	0.4887	0.070*
C13	−0.2793 (5)	−0.0249 (8)	0.4777 (2)	0.0629 (12)
H13	−0.3441	0.0118	0.4308	0.075*
C20	−0.2053 (4)	−0.1503 (8)	0.93207 (18)	0.0484 (8)
C17	0.0420 (4)	−0.1108 (5)	0.86022 (17)	0.0373 (7)
C19	−0.0979 (5)	−0.3245 (7)	0.9391 (2)	0.0505 (9)
H19	−0.1071	−0.4548	0.9677	0.061*
C16	0.1783 (4)	−0.0935 (6)	0.82225 (18)	0.0432 (8)
H16A	0.2322	−0.2406	0.8265	0.052*
H16B	0.2522	0.0200	0.8489	0.052*
C21	−0.1921 (4)	0.0430 (7)	0.8905 (2)	0.0527 (9)
H21	−0.2660	0.1606	0.8861	0.063*
C18	0.0256 (5)	−0.3028 (6)	0.9026 (2)	0.0483 (9)
H18	0.0991	−0.4210	0.9069	0.058*
C22	−0.0687 (4)	0.0617 (6)	0.8551 (2)	0.0483 (9)
H22	−0.0597	0.1934	0.8272	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C15	0.066 (3)	0.054 (2)	0.048 (2)	−0.0177 (18)	0.005 (2)	0.0067 (17)
Br1	0.0603 (3)	0.1172 (4)	0.0764 (3)	−0.0150 (3)	0.0365 (2)	−0.0046 (3)
O1	0.0571 (14)	0.0730 (16)	0.0626 (15)	−0.0087 (18)	0.0224 (12)	−0.0304 (19)
O2	0.0651 (16)	0.0468 (14)	0.0464 (14)	−0.0110 (12)	0.0053 (12)	0.0071 (12)
C2	0.0377 (17)	0.0400 (16)	0.0344 (18)	−0.0012 (13)	0.0102 (14)	−0.0027 (13)
C3	0.0426 (16)	0.0392 (17)	0.0363 (16)	−0.0034 (16)	0.0140 (13)	−0.0007 (15)
C1	0.0411 (18)	0.0488 (18)	0.0335 (18)	0.0016 (15)	0.0098 (15)	−0.0043 (15)
C5	0.0370 (15)	0.0514 (19)	0.061 (2)	0.0035 (19)	0.0156 (15)	0.000 (2)
C9	0.048 (2)	0.054 (2)	0.046 (2)	0.0073 (17)	0.0203 (17)	0.0031 (16)
C4	0.0369 (18)	0.0482 (19)	0.0384 (19)	0.0031 (14)	0.0103 (15)	0.0042 (15)
C8	0.0446 (19)	0.072 (3)	0.064 (2)	0.005 (2)	0.0229 (17)	0.022 (2)
C6	0.051 (2)	0.048 (2)	0.076 (3)	−0.0050 (17)	0.006 (2)	−0.0039 (19)
C7	0.039 (2)	0.055 (2)	0.077 (3)	−0.0069 (17)	0.007 (2)	0.012 (2)
C10	0.0439 (16)	0.0422 (18)	0.0311 (15)	−0.0046 (14)	0.0115 (13)	−0.0026 (13)
C14	0.075 (3)	0.080 (3)	0.048 (2)	−0.030 (3)	−0.013 (2)	0.004 (2)
C11	0.053 (2)	0.0432 (18)	0.040 (2)	−0.0091 (16)	0.0078 (17)	0.0028 (15)
C12	0.073 (2)	0.053 (2)	0.047 (2)	−0.001 (2)	0.008 (2)	0.0121 (18)
C13	0.070 (3)	0.068 (3)	0.044 (2)	−0.005 (2)	−0.001 (2)	0.0105 (19)
C20	0.0436 (17)	0.063 (2)	0.0409 (18)	−0.0036 (19)	0.0143 (14)	−0.0028 (19)
C17	0.0379 (16)	0.0447 (19)	0.0281 (16)	−0.0004 (13)	0.0050 (13)	−0.0031 (13)
C19	0.060 (2)	0.0500 (19)	0.043 (2)	−0.0029 (17)	0.0161 (18)	0.0090 (16)
C16	0.0408 (18)	0.056 (2)	0.0327 (17)	0.0044 (14)	0.0088 (14)	−0.0021 (14)
C21	0.050 (2)	0.052 (2)	0.058 (2)	0.0134 (17)	0.0162 (19)	0.0029 (18)
C18	0.056 (2)	0.0449 (18)	0.045 (2)	0.0126 (17)	0.0120 (18)	0.0031 (16)
C22	0.053 (2)	0.0456 (18)	0.049 (2)	0.0081 (16)	0.0165 (18)	0.0067 (16)

Geometric parameters (Å, º)

C15—C10	1.365 (5)	C10—C11	1.392 (5)
C15—C14	1.375 (5)	C14—C13	1.363 (6)
Br1—C20	1.895 (3)	C14—H14	0.9300
O1—C1	1.214 (4)	C11—C12	1.376 (5)
O2—C3	1.214 (4)	C11—H11	0.9300
C2—C1	1.526 (5)	C12—C13	1.365 (6)
C2—C3	1.533 (5)	C12—H12	0.9300
C2—C16	1.535 (4)	C13—H13	0.9300
C2—H2	0.9800	C20—C21	1.371 (6)
C3—C10	1.489 (4)	C20—C19	1.365 (6)
C1—C4	1.489 (5)	C17—C18	1.379 (5)
C5—C4	1.385 (6)	C17—C22	1.380 (5)
C5—C6	1.380 (5)	C17—C16	1.505 (5)
C5—H5	0.9300	C19—C18	1.392 (5)
C9—C8	1.382 (6)	C19—H19	0.9300
C9—C4	1.394 (5)	C16—H16A	0.9700
C9—H9	0.9300	C16—H16B	0.9700
C8—C7	1.355 (6)	C21—C22	1.376 (6)
C8—H8	0.9300	C21—H21	0.9300
C6—C7	1.363 (6)	C18—H18	0.9300
C6—H6	0.9300	C22—H22	0.9300
C7—H7	0.9300
C10—C15—C14	121.2 (3)	C13—C14—C15	120.4 (4)
C10—C15—H15	119.4	C13—C14—H14	119.8
C14—C15—H15	119.4	C15—C14—H14	119.8
C1—C2—C3	107.1 (3)	C12—C11—C10	120.0 (3)
C1—C2—C16	111.0 (3)	C12—C11—H11	120.0
C3—C2—C16	110.7 (3)	C10—C11—H11	120.0
C1—C2—H2	109.3	C13—C12—C11	120.8 (4)
C3—C2—H2	109.3	C13—C12—H12	119.6
C16—C2—H2	109.3	C11—C12—H12	119.6
O2—C3—C10	120.7 (3)	C14—C13—C12	119.3 (4)
O2—C3—C2	120.0 (3)	C14—C13—H13	120.3
C10—C3—C2	119.4 (3)	C12—C13—H13	120.4
O1—C1—C4	119.9 (3)	C21—C20—C19	121.1 (3)
O1—C1—C2	119.1 (3)	C21—C20—Br1	120.3 (3)
C4—C1—C2	121.0 (3)	C19—C20—Br1	118.6 (3)
C4—C5—C6	119.8 (3)	C18—C17—C22	117.7 (3)
C4—C5—H5	120.1	C18—C17—C16	120.0 (3)
C6—C5—H5	120.1	C22—C17—C16	122.3 (3)
C8—C9—C4	120.3 (3)	C20—C19—C18	118.5 (3)
C8—C9—H9	119.9	C20—C19—H19	120.7
C4—C9—H9	119.9	C18—C19—H19	120.7
C5—C4—C9	118.4 (3)	C17—C16—C2	113.5 (3)
C5—C4—C1	123.5 (3)	C17—C16—H16A	108.9
C9—C4—C1	118.0 (3)	C2—C16—H16A	108.9
C7—C8—C9	120.4 (4)	C17—C16—H16B	108.9
C7—C8—H8	119.8	C2—C16—H16B	108.9
C9—C8—H8	119.8	H16A—C16—H16B	107.7
C7—C6—C5	121.0 (4)	C20—C21—C22	119.4 (3)
C7—C6—H6	119.5	C20—C21—H21	120.3
C5—C6—H6	119.5	C22—C21—H21	120.3
C8—C7—C6	120.0 (4)	C17—C18—C19	121.8 (3)
C8—C7—H7	120.0	C17—C18—H18	119.1
C6—C7—H7	120.0	C19—C18—H18	119.1
C15—C10—C11	118.2 (3)	C21—C22—C17	121.5 (3)
C15—C10—C3	119.0 (3)	C21—C22—H22	119.3
C11—C10—C3	122.7 (3)	C17—C22—H22	119.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1^i	0.93	2.54	3.157 (5)	124

Symmetry code: (i) −x, y+1/2, −z+1.