2-Bromo­benzo­phenone

Details of the crystal structure and quantum chemistry calculations of the title mol­ecule, C₁₃H₉BrO, illustrate the effects of intermolecular interactions and the substitution of one of the two aromatic rings on the molecular conformation. The asymmetry of the mol­ecule is documented by the two C_aryl—C_aryl—C=O torsion angles of −68.3 (5) and −17.6 (6)°. A C—H...O hydrogen bond [H...O = 2.5 Å, C...O = 3.412 (5) Å and C—H...O = 174°] and a C—H...π contact involving the H atom at position 4 of the substituted ring and the π-system of the unsubstituted ring of an adjacent mol­ecule [H...Cg = 2.96 Å, C...Cg = 3.806 (5) Å and C—H...Cg = 153°; where Cg is the centroid of the unsubstituted ring] are observed in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.038
• wR factor = 0.064
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O1     -   C1      ..       7.16 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C1B    -   C2B     ..       9.40 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C3B    -   C4B     ..       8.29 su

Alert level C
ABSTY02_ALERT_1_C  An _exptl_absorpt_correction_type has been given without
            a literature citation. This should be contained in the
            _exptl_absorpt_process_details field.
            Absorption correction given as integration
PLAT128_ALERT_4_C Non-standard setting of Space group P21/c   ....    P21/a
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1B    -   C6B     ..       5.82 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.03
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A    ..  O1      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A    ..  CG2     ..       2.96 Ang.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK and XPREP (Siemens, 1991); program(s) used to solve structure: SHELXSS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

2-Bromobenzophenone

Crystal data

C13H9BrO	F(000) = 520
Mr = 261.11	Dx = 1.559 Mg m^−3
Monoclinic, P21/a	Melting point: 415 K
Hall symbol: -P 2yab	Mo Kα radiation, λ = 0.71073 Å
a = 7.836 (2) Å	Cell parameters from 24 reflections
b = 16.833 (4) Å	θ = 13–15°
c = 8.490 (2) Å	µ = 3.66 mm^−1
β = 96.72 (2)°	T = 293 K
V = 1112.3 (5) Å^3	Plate, colourless
Z = 4	0.35 × 0.24 × 0.1 mm

Data collection

Siemens P3/PC diffractometer	Rint = 0.075
2θ/θ scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: integration	h = 0→9
Tmin = 0.425, Tmax = 0.585	k = 0→20
2111 measured reflections	l = −10→10
1963 independent reflections	2 standard reflections every 98 reflections
1170 reflections with I > 2σ(I)	intensity decay: 2%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.038	w = 1/[σ^2(Fo^2)]
wR(F^2) = 0.064	(Δ/σ)max < 0.001
S = 0.94	Δρmax = 0.30 e Å^−3
1963 reflections	Δρmin = −0.29 e Å^−3
136 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.15616 (8)	0.80357 (3)	0.57595 (6)	0.06702 (19)
O1	−0.0740 (3)	0.96039 (16)	0.8179 (4)	0.0635 (10)
C1	0.0703 (5)	0.9364 (2)	0.8227 (5)	0.0385 (10)
C1A	0.1171 (5)	0.85401 (19)	0.8865 (4)	0.0293 (9)
C2A	0.1511 (5)	0.7898 (2)	0.7967 (4)	0.0343 (9)
C3A	0.1820 (5)	0.7154 (2)	0.8604 (5)	0.0462 (11)
H3A	0.2055	0.6731	0.7961	0.055*
C4A	0.1779 (5)	0.7045 (3)	1.0168 (5)	0.0570 (12)
H4A	0.2014	0.6545	1.0606	0.068*
C5A	0.1403 (7)	0.7649 (3)	1.1112 (5)	0.0621 (14)
H5A	0.133	0.7562	1.2184	0.075*
C6A	0.1122 (5)	0.8409 (2)	1.0462 (5)	0.0460 (11)
H6A	0.09	0.883	1.1116	0.055*
C1B	0.2062 (4)	0.98346 (19)	0.7587 (4)	0.0292 (8)
C2B	0.3802 (5)	0.9676 (2)	0.8036 (5)	0.0436 (11)
H2B	0.4121	0.9255	0.8718	0.052*
C3B	0.5040 (6)	1.0139 (3)	0.7473 (6)	0.0562 (13)
H3B	0.6195	1.0043	0.7806	0.067*
C4B	0.4583 (7)	1.0740 (3)	0.6426 (6)	0.0705 (17)
H4B	0.5423	1.1033	0.5998	0.085*
C5B	0.2814 (7)	1.0914 (3)	0.5996 (5)	0.0646 (14)
H5B	0.2486	1.1344	0.534	0.078*
C6B	0.1631 (6)	1.0454 (2)	0.6545 (5)	0.0429 (11)
H6B	0.0477	1.0553	0.6216	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.1128 (4)	0.0436 (2)	0.0490 (3)	0.0083 (4)	0.0278 (2)	−0.0059 (3)
O1	0.0255 (16)	0.0438 (17)	0.124 (3)	0.0105 (16)	0.0188 (18)	0.0032 (19)
C1	0.040 (3)	0.0185 (19)	0.057 (3)	−0.0102 (19)	0.007 (2)	−0.0032 (17)
C1A	0.033 (2)	0.0153 (16)	0.041 (2)	−0.0030 (17)	0.0098 (17)	0.0043 (15)
C2A	0.025 (2)	0.026 (2)	0.054 (2)	0.0002 (17)	0.0138 (18)	0.0053 (18)
C3A	0.055 (3)	0.028 (2)	0.057 (3)	0.002 (2)	0.016 (2)	−0.012 (2)
C4A	0.069 (3)	0.032 (2)	0.074 (3)	−0.002 (2)	0.022 (3)	0.019 (2)
C5A	0.083 (4)	0.058 (3)	0.047 (3)	−0.007 (3)	0.017 (3)	0.019 (2)
C6A	0.049 (3)	0.043 (2)	0.048 (3)	0.004 (2)	0.017 (2)	−0.004 (2)
C1B	0.022 (2)	0.0247 (18)	0.040 (2)	−0.0061 (17)	−0.0016 (17)	−0.0105 (16)
C2B	0.049 (3)	0.032 (2)	0.053 (3)	−0.008 (2)	0.018 (2)	−0.001 (2)
C3B	0.043 (3)	0.050 (3)	0.080 (3)	−0.014 (2)	0.027 (3)	0.001 (3)
C4B	0.082 (4)	0.055 (3)	0.084 (4)	−0.038 (3)	0.050 (3)	−0.022 (3)
C5B	0.100 (4)	0.039 (3)	0.059 (3)	−0.013 (3)	0.028 (3)	−0.001 (2)
C6B	0.056 (3)	0.0227 (19)	0.049 (2)	0.010 (2)	0.002 (2)	0.0082 (18)

Geometric parameters (Å, º)

Br1—C2A	1.893 (4)	C6A—H6A	0.93
O1—C1	1.197 (4)	C1B—C6B	1.383 (5)
C1—C1B	1.480 (5)	C1B—C2B	1.398 (5)
C1—C1A	1.519 (4)	C2B—C3B	1.374 (5)
C1A—C2A	1.367 (5)	C2B—H2B	0.93
C1A—C6A	1.379 (5)	C3B—C4B	1.367 (6)
C2A—C3A	1.373 (5)	C3B—H3B	0.93
C3A—C4A	1.344 (5)	C4B—C5B	1.422 (6)
C3A—H3A	0.93	C4B—H4B	0.93
C4A—C5A	1.348 (6)	C5B—C6B	1.333 (5)
C4A—H4A	0.93	C5B—H5B	0.93
C5A—C6A	1.400 (5)	C6B—H6B	0.93
C5A—H5A	0.93
O1—C1—C1B	121.6 (3)	C5A—C6A—H6A	119.6
O1—C1—C1A	120.5 (3)	C6B—C1B—C2B	118.4 (4)
C1B—C1—C1A	117.7 (3)	C6B—C1B—C1	120.4 (4)
C2A—C1A—C6A	116.8 (3)	C2B—C1B—C1	121.2 (4)
C2A—C1A—C1	125.4 (3)	C3B—C2B—C1B	120.2 (4)
C6A—C1A—C1	117.6 (3)	C3B—C2B—H2B	119.9
C1A—C2A—C3A	122.5 (4)	C1B—C2B—H2B	119.9
C1A—C2A—Br1	118.9 (3)	C4B—C3B—C2B	120.3 (5)
C3A—C2A—Br1	118.6 (3)	C4B—C3B—H3B	119.8
C4A—C3A—C2A	119.4 (4)	C2B—C3B—H3B	119.8
C4A—C3A—H3A	120.3	C3B—C4B—C5B	119.5 (4)
C2A—C3A—H3A	120.3	C3B—C4B—H4B	120.2
C3A—C4A—C5A	121.1 (4)	C5B—C4B—H4B	120.2
C3A—C4A—H4A	119.5	C6B—C5B—C4B	119.2 (4)
C5A—C4A—H4A	119.5	C6B—C5B—H5B	120.4
C4A—C5A—C6A	119.3 (4)	C4B—C5B—H5B	120.4
C4A—C5A—H5A	120.3	C5B—C6B—C1B	122.3 (4)
C6A—C5A—H5A	120.3	C5B—C6B—H6B	118.9
C1A—C6A—C5A	120.9 (4)	C1B—C6B—H6B	118.9
C1A—C6A—H6A	119.6
O1—C1—C1A—C2A	106.4 (5)	C4A—C5A—C6A—C1A	2.1 (8)
C1B—C1—C1A—C2A	−70.0 (5)	O1—C1—C1B—C6B	−17.6 (6)
O1—C1—C1A—C6A	−68.3 (5)	C1A—C1—C1B—C6B	158.8 (3)
C1B—C1—C1A—C6A	115.3 (4)	O1—C1—C1B—C2B	161.3 (4)
C6A—C1A—C2A—C3A	−1.0 (6)	C1A—C1—C1B—C2B	−22.4 (5)
C1—C1A—C2A—C3A	−175.7 (4)	C6B—C1B—C2B—C3B	1.3 (6)
C6A—C1A—C2A—Br1	179.0 (3)	C1—C1B—C2B—C3B	−177.5 (4)
C1—C1A—C2A—Br1	4.3 (5)	C1B—C2B—C3B—C4B	−2.4 (6)
C1A—C2A—C3A—C4A	0.4 (6)	C2B—C3B—C4B—C5B	3.8 (7)
Br1—C2A—C3A—C4A	−179.6 (3)	C3B—C4B—C5B—C6B	−4.3 (7)
C2A—C3A—C4A—C5A	1.5 (7)	C4B—C5B—C6B—C1B	3.4 (6)
C3A—C4A—C5A—C6A	−2.7 (8)	C2B—C1B—C6B—C5B	−1.9 (6)
C2A—C1A—C6A—C5A	−0.3 (6)	C1—C1B—C6B—C5B	177.0 (4)
C1—C1A—C6A—C5A	174.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3B—H3B···O1^i	0.93	2.50	3.412 (5)	168
C6A—H6A···O1^ii	0.93	2.71	3.562 (5)	153
C4A—H4A···Cg2^iii	0.93	2.96	3.806 (5)	153

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