2,3-Dibromo-3-(4-methoxy­phen­yl)-1-phenyl­propan-1-one

In the title compound, C₁₆H₁₄Br₂O₂, the C-Br bond lengths are dsignificantly different. One of the Br atoms participates in weak hydrogen-bonding inter­actions with C-H groups from adjoining mol­ecules.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.048
• wR factor = 0.137
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O2      ..       3.30 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A    ..  BR2     ..       3.03 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A    ..  BR2     ..       3.02 Ang.

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

2,3-Dibromo-3-(4-methoxyphenyl)-1-phenylpropan-1-one

Crystal data

C16H14Br2O2	Z = 2
Mr = 398.09	F(000) = 392
Triclinic, P1	Dx = 1.717 Mg m^−3
a = 5.9055 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.133 (3) Å	Cell parameters from 2368 reflections
c = 14.584 (5) Å	θ = 2.3–27.1°
α = 101.028 (4)°	µ = 5.26 mm^−1
β = 90.411 (4)°	T = 293 K
γ = 94.264 (5)°	Plate, colorless
V = 769.8 (4) Å^3	0.33 × 0.26 × 0.16 mm

Data collection

Bruker APEX-II CCD area-detector diffractometer	3711 independent reflections
Radiation source: fine-focus sealed tube	2452 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 28.2°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
Tmin = 0.227, Tmax = 0.451	k = −12→12
7685 measured reflections	l = −19→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.137	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0804P)^2] where P = (Fo^2 + 2Fc^2)/3
3711 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 1.12 e Å^−3
0 restraints	Δρmin = −1.00 e Å^−3

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	0.04261 (8)	0.79601 (5)	0.29733 (3)	0.06189 (18)
Br2	0.60934 (7)	1.09478 (5)	0.18794 (3)	0.05362 (17)
O1	0.4756 (6)	0.7172 (4)	0.1534 (2)	0.0700 (9)
O2	0.2405 (6)	1.4333 (4)	0.5870 (2)	0.0694 (9)
C1	0.1772 (7)	0.7417 (4)	0.0519 (3)	0.0453 (9)
C2	0.2495 (9)	0.6316 (5)	−0.0186 (3)	0.0612 (12)
H2A	0.3835	0.5881	−0.0098	0.073*
C3	0.1283 (11)	0.5854 (6)	−0.1011 (3)	0.0760 (16)
H3A	0.1796	0.5105	−0.1469	0.091*
C4	−0.0689 (12)	0.6495 (7)	−0.1161 (3)	0.0819 (17)
H4A	−0.1513	0.6179	−0.1718	0.098*
C5	−0.1439 (9)	0.7611 (6)	−0.0478 (3)	0.0735 (14)
H5A	−0.2757	0.8060	−0.0579	0.088*
C6	−0.0222 (8)	0.8060 (5)	0.0359 (3)	0.0568 (11)
H6A	−0.0746	0.8800	0.0820	0.068*
C7	0.3108 (7)	0.7820 (4)	0.1400 (3)	0.0478 (9)
C8	0.2339 (7)	0.9048 (4)	0.2181 (3)	0.0450 (9)
H8A	0.1444	0.9734	0.1916	0.054*
C9	0.4294 (6)	0.9903 (4)	0.2765 (3)	0.0436 (9)
H9A	0.5237	0.9186	0.2974	0.052*
C10	0.3729 (6)	1.1050 (4)	0.3603 (3)	0.0432 (9)
C11	0.5272 (7)	1.1389 (5)	0.4347 (3)	0.0495 (10)
H11A	0.6576	1.0874	0.4327	0.059*
C12	0.4907 (8)	1.2483 (5)	0.5122 (3)	0.0546 (11)
H12A	0.5965	1.2702	0.5613	0.066*
C13	0.2974 (8)	1.3243 (5)	0.5159 (3)	0.0520 (10)
C14	0.1388 (8)	1.2905 (5)	0.4415 (3)	0.0559 (11)
H14A	0.0069	1.3406	0.4437	0.067*
C15	0.1805 (7)	1.1824 (5)	0.3651 (3)	0.0535 (10)
H15A	0.0760	1.1612	0.3154	0.064*
C16	0.4077 (11)	1.4841 (6)	0.6614 (3)	0.0821 (17)
H16A	0.3603	1.5720	0.7016	0.123*
H16B	0.5515	1.5073	0.6352	0.123*
H16C	0.4221	1.4068	0.6969	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0509 (3)	0.0699 (3)	0.0598 (3)	−0.0149 (2)	0.0021 (2)	0.0072 (2)
Br2	0.0497 (3)	0.0573 (3)	0.0531 (3)	0.00143 (19)	0.00993 (19)	0.0094 (2)
O1	0.057 (2)	0.066 (2)	0.081 (2)	0.0256 (17)	−0.0153 (17)	−0.0070 (17)
O2	0.087 (2)	0.065 (2)	0.0486 (17)	−0.0019 (18)	0.0058 (16)	−0.0066 (15)
C1	0.046 (2)	0.042 (2)	0.044 (2)	−0.0008 (17)	0.0042 (17)	0.0020 (17)
C2	0.069 (3)	0.048 (2)	0.063 (3)	0.009 (2)	0.022 (2)	0.000 (2)
C3	0.107 (5)	0.066 (3)	0.044 (3)	−0.014 (3)	0.021 (3)	−0.012 (2)
C4	0.114 (5)	0.087 (4)	0.038 (2)	−0.022 (4)	−0.012 (3)	0.005 (3)
C5	0.073 (3)	0.088 (4)	0.055 (3)	0.006 (3)	−0.018 (2)	0.005 (3)
C6	0.050 (3)	0.061 (3)	0.053 (2)	0.008 (2)	−0.006 (2)	−0.004 (2)
C7	0.039 (2)	0.045 (2)	0.055 (2)	0.0055 (18)	−0.0003 (18)	−0.0003 (19)
C8	0.039 (2)	0.049 (2)	0.045 (2)	0.0046 (17)	−0.0041 (17)	0.0026 (18)
C9	0.036 (2)	0.049 (2)	0.045 (2)	0.0014 (17)	−0.0021 (16)	0.0079 (17)
C10	0.038 (2)	0.049 (2)	0.042 (2)	0.0001 (17)	−0.0025 (16)	0.0067 (17)
C11	0.041 (2)	0.060 (2)	0.048 (2)	0.0020 (18)	−0.0072 (17)	0.0114 (19)
C12	0.058 (3)	0.065 (3)	0.038 (2)	−0.006 (2)	−0.0094 (19)	0.006 (2)
C13	0.059 (3)	0.055 (2)	0.038 (2)	−0.007 (2)	0.0068 (19)	0.0041 (18)
C14	0.047 (3)	0.057 (3)	0.058 (3)	0.005 (2)	0.001 (2)	−0.002 (2)
C15	0.043 (2)	0.060 (3)	0.053 (2)	0.0038 (19)	−0.0080 (19)	−0.002 (2)
C16	0.123 (5)	0.073 (3)	0.039 (2)	−0.012 (3)	0.005 (3)	−0.009 (2)

Geometric parameters (Å, º)

Br1—C8	1.973 (4)	C8—C9	1.505 (6)
Br2—C9	2.012 (4)	C8—H8A	0.9800
O1—C7	1.210 (5)	C9—C10	1.507 (5)
O2—C13	1.355 (5)	C9—H9A	0.9800
O2—C16	1.447 (7)	C10—C15	1.377 (5)
C1—C2	1.388 (6)	C10—C11	1.385 (6)
C1—C6	1.391 (6)	C11—C12	1.387 (6)
C1—C7	1.473 (6)	C11—H11A	0.9300
C2—C3	1.373 (8)	C12—C13	1.375 (6)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.376 (8)	C13—C14	1.402 (6)
C3—H3A	0.9300	C14—C15	1.377 (6)
C4—C5	1.383 (8)	C14—H14A	0.9300
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.388 (6)	C16—H16A	0.9600
C5—H5A	0.9300	C16—H16B	0.9600
C6—H6A	0.9300	C16—H16C	0.9600
C7—C8	1.534 (5)
C13—O2—C16	117.0 (4)	C8—C9—Br2	104.7 (3)
C2—C1—C6	117.7 (4)	C10—C9—Br2	108.7 (3)
C2—C1—C7	118.8 (4)	C8—C9—H9A	108.6
C6—C1—C7	123.5 (4)	C10—C9—H9A	108.6
C3—C2—C1	121.6 (5)	Br2—C9—H9A	108.6
C3—C2—H2A	119.2	C15—C10—C11	118.3 (4)
C1—C2—H2A	119.2	C15—C10—C9	123.4 (4)
C2—C3—C4	120.2 (5)	C11—C10—C9	118.3 (4)
C2—C3—H3A	119.9	C10—C11—C12	121.2 (4)
C4—C3—H3A	119.9	C10—C11—H11A	119.4
C3—C4—C5	119.6 (5)	C12—C11—H11A	119.4
C3—C4—H4A	120.2	C13—C12—C11	119.7 (4)
C5—C4—H4A	120.2	C13—C12—H12A	120.1
C4—C5—C6	119.9 (5)	C11—C12—H12A	120.1
C4—C5—H5A	120.0	O2—C13—C12	125.9 (4)
C6—C5—H5A	120.0	O2—C13—C14	114.3 (4)
C5—C6—C1	120.9 (4)	C12—C13—C14	119.7 (4)
C5—C6—H6A	119.5	C15—C14—C13	119.3 (4)
C1—C6—H6A	119.5	C15—C14—H14A	120.4
O1—C7—C1	121.5 (4)	C13—C14—H14A	120.4
O1—C7—C8	119.2 (4)	C14—C15—C10	121.7 (4)
C1—C7—C8	119.3 (3)	C14—C15—H15A	119.1
C9—C8—C7	112.8 (3)	C10—C15—H15A	119.1
C9—C8—Br1	108.8 (3)	O2—C16—H16A	109.5
C7—C8—Br1	104.5 (3)	O2—C16—H16B	109.5
C9—C8—H8A	110.2	H16A—C16—H16B	109.5
C7—C8—H8A	110.2	O2—C16—H16C	109.5
Br1—C8—H8A	110.2	H16A—C16—H16C	109.5
C8—C9—C10	117.4 (3)	H16B—C16—H16C	109.5
C6—C1—C2—C3	−0.9 (7)	C7—C8—C9—Br2	64.5 (4)
C7—C1—C2—C3	177.7 (4)	Br1—C8—C9—Br2	179.91 (16)
C1—C2—C3—C4	0.8 (8)	C8—C9—C10—C15	−29.6 (6)
C2—C3—C4—C5	0.2 (8)	Br2—C9—C10—C15	88.9 (4)
C3—C4—C5—C6	−1.1 (8)	C8—C9—C10—C11	153.4 (4)
C4—C5—C6—C1	1.0 (8)	Br2—C9—C10—C11	−88.1 (4)
C2—C1—C6—C5	0.0 (7)	C15—C10—C11—C12	−0.2 (6)
C7—C1—C6—C5	−178.5 (4)	C9—C10—C11—C12	177.0 (4)
C2—C1—C7—O1	−3.1 (6)	C10—C11—C12—C13	0.4 (7)
C6—C1—C7—O1	175.4 (4)	C16—O2—C13—C12	6.2 (6)
C2—C1—C7—C8	179.3 (4)	C16—O2—C13—C14	−173.8 (4)
C6—C1—C7—C8	−2.2 (6)	C11—C12—C13—O2	−180.0 (4)
O1—C7—C8—C9	33.4 (6)	C11—C12—C13—C14	0.0 (7)
C1—C7—C8—C9	−149.0 (4)	O2—C13—C14—C15	179.4 (4)
O1—C7—C8—Br1	−84.6 (4)	C12—C13—C14—C15	−0.6 (7)
C1—C7—C8—Br1	93.0 (4)	C13—C14—C15—C10	0.9 (7)
C7—C8—C9—C10	−174.9 (3)	C11—C10—C15—C14	−0.4 (6)
Br1—C8—C9—C10	−59.5 (4)	C9—C10—C15—C14	−177.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Br2^i	0.93	3.03	3.867 (5)	151
C6—H6A···Br2^ii	0.93	3.02	3.911 (5)	160

Symmetry codes: (i) −x, −y+2, −z; (ii) x−1, y, z.