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In its crystal structure, the title compound, C8H7BrO2, displays an intra­molecular O—H...O hydrogen bond. Adjacent mol­ecules are linked into chains by a C—Br...O inter­action.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011348/hb2317sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011348/hb2317Isup2.hkl
Contains datablock I

CCDC reference: 643010

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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
C8H7BrO2Z = 2
Mr = 215.05F(000) = 212
Triclinic, P1Dx = 1.854 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1098 (1) ÅCell parameters from 4168 reflections
b = 7.7472 (1) Åθ = 2.7–32.9°
c = 7.8345 (1) ŵ = 5.28 mm1
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 tube1226 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω scansθmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.058, Tmax = 0.178k = 99
4967 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-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 parametersΔρmax = 2.27 e Å3
0 restraintsΔρmin = 2.25 e Å3
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
xyzUiso*/Ueq
Br10.85713 (9)0.65112 (8)0.88947 (7)0.0247 (4)
O10.3468 (7)0.8763 (6)0.1647 (6)0.0262 (11)
O20.1199 (7)0.7629 (6)0.3733 (7)0.0250 (10)
H20.14320.79290.27630.038*
C10.4769 (10)0.7773 (8)0.4412 (8)0.0192 (13)
C20.2886 (9)0.7349 (8)0.4826 (9)0.0182 (13)
C30.2653 (11)0.6611 (9)0.6419 (9)0.0228 (14)
H30.13460.62830.66700.027*
C40.4354 (11)0.6370 (8)0.7615 (9)0.0218 (14)
H40.42310.58910.87060.026*
C50.6240 (9)0.6832 (8)0.7210 (8)0.0176 (13)
C60.6465 (10)0.7515 (8)0.5647 (9)0.0196 (13)
H60.77710.78140.53990.024*
C70.4971 (11)0.8525 (8)0.2705 (8)0.0209 (13)
C80.7019 (11)0.8985 (9)0.2270 (9)0.0236 (14)
H8A0.68880.94570.11050.035*
H8B0.73490.78620.22280.035*
H8C0.81520.99340.31940.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0187 (5)0.0348 (5)0.0188 (5)0.0132 (3)0.0012 (3)0.0045 (3)
O10.018 (3)0.030 (2)0.022 (2)0.008 (2)0.004 (2)0.005 (2)
O20.014 (2)0.029 (2)0.028 (3)0.008 (2)0.001 (2)0.006 (2)
C10.018 (3)0.017 (3)0.020 (3)0.007 (2)0.000 (3)0.000 (2)
C20.008 (3)0.017 (3)0.024 (3)0.004 (2)0.003 (2)0.001 (2)
C30.015 (3)0.024 (3)0.026 (4)0.008 (3)0.002 (3)0.000 (3)
C40.025 (4)0.017 (3)0.019 (3)0.005 (3)0.003 (3)0.004 (2)
C50.012 (3)0.018 (3)0.018 (3)0.006 (2)0.003 (2)0.001 (2)
C60.010 (3)0.022 (3)0.024 (3)0.007 (2)0.001 (3)0.000 (2)
C70.027 (4)0.016 (3)0.014 (3)0.006 (3)0.001 (3)0.002 (2)
C80.025 (4)0.026 (3)0.018 (3)0.011 (3)0.003 (3)0.003 (3)
Geometric parameters (Å, º) top
Br1—C51.908 (6)C3—H30.9500
O1—C71.232 (8)C4—C51.388 (9)
O2—C21.357 (8)C4—H40.9500
O2—H20.8400C5—C61.367 (9)
C1—C21.392 (9)C6—H60.9500
C1—C61.400 (9)C7—C81.508 (10)
C1—C71.487 (9)C8—H8A0.9800
C2—C31.405 (9)C8—H8B0.9800
C3—C41.383 (9)C8—H8C0.9800
C2—O2—H2109.5C6—C5—Br1119.6 (5)
C2—C1—C6118.6 (6)C4—C5—Br1118.8 (5)
C2—C1—C7120.2 (6)C5—C6—C1120.0 (6)
C6—C1—C7121.2 (6)C5—C6—H6120.0
O2—C2—C1122.2 (6)C1—C6—H6120.0
O2—C2—C3116.7 (6)O1—C7—C1120.1 (6)
C1—C2—C3121.1 (6)O1—C7—C8120.1 (6)
C4—C3—C2119.0 (6)C1—C7—C8119.8 (6)
C4—C3—H3120.5C7—C8—H8A109.5
C2—C3—H3120.5C7—C8—H8B109.5
C3—C4—C5119.6 (6)H8A—C8—H8B109.5
C3—C4—H4120.2C7—C8—H8C109.5
C5—C4—H4120.2H8A—C8—H8C109.5
C6—C5—C4121.6 (6)H8B—C8—H8C109.5
C6—C1—C2—O2177.3 (5)C4—C5—C6—C10.3 (9)
C7—C1—C2—O21.3 (9)Br1—C5—C6—C1179.3 (4)
C6—C1—C2—C32.3 (9)C2—C1—C6—C51.0 (9)
C7—C1—C2—C3179.0 (5)C7—C1—C6—C5179.6 (5)
O2—C2—C3—C4177.4 (5)C2—C1—C7—O10.4 (9)
C1—C2—C3—C42.3 (9)C6—C1—C7—O1179.1 (5)
C2—C3—C4—C51.0 (9)C2—C1—C7—C8179.9 (5)
C3—C4—C5—C60.3 (9)C6—C1—C7—C81.2 (9)
C3—C4—C5—Br1179.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.841.822.556 (6)145
 

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