Details of the crystal structure and quantum chemistry calculations of the title molecule, C
13H
9BrO, 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.
Supporting information
CCDC reference: 270465
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
Crystal data top
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) Å3 | Plate, colourless |
Z = 4 | 0.35 × 0.24 × 0.1 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2)] |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3B—H3B···O1i | 0.93 | 2.50 | 3.412 (5) | 168 |
C6A—H6A···O1ii | 0.93 | 2.71 | 3.562 (5) | 153 |
C4A—H4A···Cg2iii | 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. |