organic compounds
In its crystal structure, the title compound, C8H7BrO2, displays an intramolecular O—HO hydrogen bond. Adjacent molecules are linked into chains by a C—BrO interaction.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011348/hb2317sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011348/hb2317Isup2.hkl |
CCDC reference: 643010
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.010 Å
- R factor = 0.064
- wR factor = 0.180
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level A ABSTM02_ALERT_3_A The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 Tmin and Tmax reported: 0.058 0.178 Tmin(prime) and Tmax expected: 0.055 0.071 RR(prime) = 0.420 Please check that your absorption correction is appropriate.
Author Response: The ratio is given by SADABS. The range is somewhat narrowed when an additional spherical correction (\mr = 0.5) was applied, and the high-angle reflections omitted. |
PLAT061_ALERT_3_A Tmax/Tmin Range Test RR' too Large ............. 0.26
Author Response: As above. |
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.40 PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 10 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 6 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C8 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O1 .. 3.36 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.402 Tmax scaled 0.071 Tmin scaled 0.023
Author Response: The ratio is given by SADABS. The range is somewhat narrowed when an additional spherical correction (\mr = 0.5) was applied, and the high-angle reflections omitted. |
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).
5'-Bromo-2'-hydroxyacetophenone top
Crystal data top
C8H7BrO2 | Z = 2 |
Mr = 215.05 | F(000) = 212 |
Triclinic, P1 | Dx = 1.854 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1098 (1) Å | Cell parameters from 4168 reflections |
b = 7.7472 (1) Å | θ = 2.7–32.9° |
c = 7.8345 (1) Å | µ = 5.28 mm−1 |
α = 90.655 (1)° | T = 173 K |
β = 106.038 (1)° | Block, colorless |
γ = 110.690 (1)° | 0.50 × 0.50 × 0.50 mm |
V = 385.12 (1) Å3 |
Data collection top
Bruker APEX II CCD diffractometer | 1347 independent reflections |
Radiation source: medium-focus sealed tube | 1226 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.058, Tmax = 0.178 | k = −9→9 |
4967 measured reflections | l = −9→9 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.180 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1417P)2 + 0.6382P] where P = (Fo2 + 2Fc2)/3 |
1347 reflections | (Δ/σ)max = 0.001 |
102 parameters | Δρmax = 2.27 e Å−3 |
0 restraints | Δρmin = −2.25 e Å−3 |
Special details top
Experimental. A medium-focus collimator of 0.8 mm was used on the diffractometer. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.85713 (9) | 0.65112 (8) | 0.88947 (7) | 0.0247 (4) | |
O1 | 0.3468 (7) | 0.8763 (6) | 0.1647 (6) | 0.0262 (11) | |
O2 | 0.1199 (7) | 0.7629 (6) | 0.3733 (7) | 0.0250 (10) | |
H2 | 0.1432 | 0.7929 | 0.2763 | 0.038* | |
C1 | 0.4769 (10) | 0.7773 (8) | 0.4412 (8) | 0.0192 (13) | |
C2 | 0.2886 (9) | 0.7349 (8) | 0.4826 (9) | 0.0182 (13) | |
C3 | 0.2653 (11) | 0.6611 (9) | 0.6419 (9) | 0.0228 (14) | |
H3 | 0.1346 | 0.6283 | 0.6670 | 0.027* | |
C4 | 0.4354 (11) | 0.6370 (8) | 0.7615 (9) | 0.0218 (14) | |
H4 | 0.4231 | 0.5891 | 0.8706 | 0.026* | |
C5 | 0.6240 (9) | 0.6832 (8) | 0.7210 (8) | 0.0176 (13) | |
C6 | 0.6465 (10) | 0.7515 (8) | 0.5647 (9) | 0.0196 (13) | |
H6 | 0.7771 | 0.7814 | 0.5399 | 0.024* | |
C7 | 0.4971 (11) | 0.8525 (8) | 0.2705 (8) | 0.0209 (13) | |
C8 | 0.7019 (11) | 0.8985 (9) | 0.2270 (9) | 0.0236 (14) | |
H8A | 0.6888 | 0.9457 | 0.1105 | 0.035* | |
H8B | 0.7349 | 0.7862 | 0.2228 | 0.035* | |
H8C | 0.8152 | 0.9934 | 0.3194 | 0.035* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0187 (5) | 0.0348 (5) | 0.0188 (5) | 0.0132 (3) | −0.0012 (3) | 0.0045 (3) |
O1 | 0.018 (3) | 0.030 (2) | 0.022 (2) | 0.008 (2) | −0.004 (2) | 0.005 (2) |
O2 | 0.014 (2) | 0.029 (2) | 0.028 (3) | 0.008 (2) | 0.001 (2) | 0.006 (2) |
C1 | 0.018 (3) | 0.017 (3) | 0.020 (3) | 0.007 (2) | 0.000 (3) | 0.000 (2) |
C2 | 0.008 (3) | 0.017 (3) | 0.024 (3) | 0.004 (2) | −0.003 (2) | −0.001 (2) |
C3 | 0.015 (3) | 0.024 (3) | 0.026 (4) | 0.008 (3) | 0.002 (3) | 0.000 (3) |
C4 | 0.025 (4) | 0.017 (3) | 0.019 (3) | 0.005 (3) | 0.003 (3) | 0.004 (2) |
C5 | 0.012 (3) | 0.018 (3) | 0.018 (3) | 0.006 (2) | −0.003 (2) | −0.001 (2) |
C6 | 0.010 (3) | 0.022 (3) | 0.024 (3) | 0.007 (2) | −0.001 (3) | 0.000 (2) |
C7 | 0.027 (4) | 0.016 (3) | 0.014 (3) | 0.006 (3) | 0.001 (3) | 0.002 (2) |
C8 | 0.025 (4) | 0.026 (3) | 0.018 (3) | 0.011 (3) | 0.003 (3) | 0.003 (3) |
Geometric parameters (Å, º) top
Br1—C5 | 1.908 (6) | C3—H3 | 0.9500 |
O1—C7 | 1.232 (8) | C4—C5 | 1.388 (9) |
O2—C2 | 1.357 (8) | C4—H4 | 0.9500 |
O2—H2 | 0.8400 | C5—C6 | 1.367 (9) |
C1—C2 | 1.392 (9) | C6—H6 | 0.9500 |
C1—C6 | 1.400 (9) | C7—C8 | 1.508 (10) |
C1—C7 | 1.487 (9) | C8—H8A | 0.9800 |
C2—C3 | 1.405 (9) | C8—H8B | 0.9800 |
C3—C4 | 1.383 (9) | C8—H8C | 0.9800 |
C2—O2—H2 | 109.5 | C6—C5—Br1 | 119.6 (5) |
C2—C1—C6 | 118.6 (6) | C4—C5—Br1 | 118.8 (5) |
C2—C1—C7 | 120.2 (6) | C5—C6—C1 | 120.0 (6) |
C6—C1—C7 | 121.2 (6) | C5—C6—H6 | 120.0 |
O2—C2—C1 | 122.2 (6) | C1—C6—H6 | 120.0 |
O2—C2—C3 | 116.7 (6) | O1—C7—C1 | 120.1 (6) |
C1—C2—C3 | 121.1 (6) | O1—C7—C8 | 120.1 (6) |
C4—C3—C2 | 119.0 (6) | C1—C7—C8 | 119.8 (6) |
C4—C3—H3 | 120.5 | C7—C8—H8A | 109.5 |
C2—C3—H3 | 120.5 | C7—C8—H8B | 109.5 |
C3—C4—C5 | 119.6 (6) | H8A—C8—H8B | 109.5 |
C3—C4—H4 | 120.2 | C7—C8—H8C | 109.5 |
C5—C4—H4 | 120.2 | H8A—C8—H8C | 109.5 |
C6—C5—C4 | 121.6 (6) | H8B—C8—H8C | 109.5 |
C6—C1—C2—O2 | 177.3 (5) | C4—C5—C6—C1 | 0.3 (9) |
C7—C1—C2—O2 | −1.3 (9) | Br1—C5—C6—C1 | −179.3 (4) |
C6—C1—C2—C3 | −2.3 (9) | C2—C1—C6—C5 | 1.0 (9) |
C7—C1—C2—C3 | 179.0 (5) | C7—C1—C6—C5 | 179.6 (5) |
O2—C2—C3—C4 | −177.4 (5) | C2—C1—C7—O1 | −0.4 (9) |
C1—C2—C3—C4 | 2.3 (9) | C6—C1—C7—O1 | −179.1 (5) |
C2—C3—C4—C5 | −1.0 (9) | C2—C1—C7—C8 | 179.9 (5) |
C3—C4—C5—C6 | −0.3 (9) | C6—C1—C7—C8 | 1.2 (9) |
C3—C4—C5—Br1 | 179.3 (4) |