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In the structure of the title compound, C12H9BrO2, all bond lengths and angles are normal. There is an O—H...O intramolecular hydrogen bond and a weak intermolecular C—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804021889/fl6117sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804021889/fl6117Isup2.hkl
Contains datablock I

CCDC reference: 252984

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • R factor = 0.052
  • wR factor = 0.135
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

2-Bromo-1-(1-hydroxynaphthalene-2-yl)ethanone top
Crystal data top
C12H9BrO2F(000) = 528
Mr = 265.10Dx = 1.701 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 4.9207 (5) ÅCell parameters from 12498 reflections
b = 10.5041 (10) Åθ = 1.9–27.1°
c = 20.357 (2) ŵ = 3.94 mm1
β = 100.293 (8)°T = 293 K
V = 1035.28 (18) Å3Plate, colourless
Z = 40.50 × 0.23 × 0.02 mm
Data collection top
STOE IPDS-II
diffractometer
2007 independent reflections
Radiation source: fine-focus sealed tube842 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.092
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.0°
Ω scanh = 56
Absorption correction: integration
X-RED32 (Stoe & Cie, 2002)
k = 1212
Tmin = 0.309, Tmax = 0.794l = 2525
7371 measured reflections
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 0.87 w = 1/[σ2(Fo2) + (0.0602P)2]
where P = (Fo2 + 2Fc2)/3
2007 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.61 e Å3
0 restraintsΔρmin = 0.59 e Å3
Special details top

Experimental. Instruments: Melting points were determinated with a Thomas Hoover capillary melting point apparatus and are uncorrected·IR spectra were recorded in KBr disks with a Bruker vector 22 IR Spectrometer 1H-NMR spectra were recorded on a Bruker 80 MHz and the chemical shifts was reported as (p.p.m.) values. Splitting patterns are designated as follows: s: singlet and m: multiplet.

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 (Å2) top
xyzUiso*/Ueq
O20.0836 (10)0.0531 (4)0.3542 (2)0.0587 (14)
H2O0.05460.04060.32590.088*
Br10.72337 (15)0.25234 (9)0.16152 (4)0.0773 (3)
C80.0320 (13)0.2669 (6)0.3189 (3)0.0447 (16)
O10.3360 (10)0.1106 (4)0.2656 (2)0.0570 (12)
C110.2695 (13)0.2229 (6)0.2711 (3)0.0453 (17)
C70.1395 (13)0.1805 (6)0.3584 (3)0.0445 (16)
C60.3720 (14)0.2173 (5)0.4045 (3)0.0450 (18)
C10.4335 (15)0.3506 (6)0.4116 (3)0.0472 (17)
C90.0400 (14)0.3992 (6)0.3282 (3)0.0508 (18)
H90.07040.45970.30280.061*
C20.6664 (16)0.3871 (7)0.4579 (3)0.061 (2)
H20.70960.47310.46300.073*
C100.2584 (15)0.4383 (6)0.3716 (3)0.0526 (18)
H100.29680.52490.37580.063*
C30.8305 (16)0.3011 (8)0.4955 (4)0.064 (2)
H30.98540.32790.52540.077*
C40.7645 (16)0.1709 (8)0.4889 (4)0.067 (2)
H40.87350.11160.51550.080*
C50.5443 (15)0.1312 (7)0.4443 (3)0.058 (2)
H50.50660.04460.43990.069*
C120.4318 (14)0.3209 (6)0.2264 (3)0.0544 (18)
H12A0.30630.36720.20340.065*
H12B0.50990.38130.25390.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.064 (3)0.029 (2)0.081 (3)0.002 (2)0.004 (3)0.003 (2)
Br10.0750 (5)0.0705 (5)0.0777 (5)0.0110 (6)0.0100 (3)0.0114 (5)
C80.055 (4)0.032 (4)0.051 (3)0.003 (3)0.020 (3)0.005 (3)
O10.062 (3)0.033 (3)0.074 (3)0.006 (2)0.007 (2)0.008 (2)
C110.049 (4)0.041 (5)0.049 (3)0.002 (3)0.015 (3)0.010 (3)
C70.055 (4)0.026 (3)0.054 (4)0.003 (3)0.014 (3)0.004 (3)
C60.052 (4)0.036 (5)0.049 (3)0.005 (3)0.016 (3)0.003 (3)
C10.058 (4)0.045 (4)0.042 (4)0.014 (4)0.020 (3)0.007 (3)
C90.059 (5)0.038 (4)0.058 (4)0.000 (3)0.019 (4)0.000 (3)
C20.072 (5)0.059 (4)0.051 (4)0.024 (4)0.010 (4)0.009 (4)
C100.066 (5)0.035 (4)0.061 (4)0.013 (3)0.022 (4)0.004 (3)
C30.052 (5)0.082 (5)0.058 (5)0.011 (4)0.007 (4)0.002 (4)
C40.062 (5)0.079 (6)0.055 (5)0.001 (5)0.001 (4)0.005 (4)
C50.066 (5)0.048 (4)0.057 (4)0.002 (4)0.006 (4)0.009 (4)
C120.055 (4)0.039 (4)0.068 (4)0.001 (3)0.009 (4)0.006 (3)
Geometric parameters (Å, º) top
O2—C71.366 (7)C9—C101.329 (8)
O2—H2O0.8200C9—H90.9300
Br1—C121.909 (6)C2—C31.354 (10)
C8—C71.392 (8)C2—H20.9300
C8—C91.439 (9)C10—H100.9300
C8—C111.456 (8)C3—C41.407 (10)
O1—C111.224 (7)C3—H30.9300
C11—C121.506 (8)C4—C51.349 (9)
C7—C61.399 (8)C4—H40.9300
C6—C51.394 (8)C5—H50.9300
C6—C11.435 (9)C12—H12A0.9700
C1—C21.402 (9)C12—H12B0.9700
C1—C101.415 (9)
C7—O2—H2O109.5C3—C2—H2118.9
C7—C8—C9116.4 (5)C1—C2—H2118.9
C7—C8—C11120.7 (6)C9—C10—C1121.3 (6)
C9—C8—C11122.9 (6)C9—C10—H10119.4
O1—C11—C8122.4 (5)C1—C10—H10119.4
O1—C11—C12119.9 (6)C2—C3—C4119.3 (7)
C8—C11—C12117.6 (5)C2—C3—H3120.3
O2—C7—C8120.5 (5)C4—C3—H3120.3
O2—C7—C6116.3 (5)C5—C4—C3120.6 (7)
C8—C7—C6123.1 (6)C5—C4—H4119.7
C5—C6—C7123.4 (6)C3—C4—H4119.7
C5—C6—C1118.6 (6)C4—C5—C6121.5 (7)
C7—C6—C1118.0 (5)C4—C5—H5119.3
C2—C1—C10123.4 (6)C6—C5—H5119.3
C2—C1—C6117.8 (6)C11—C12—Br1114.4 (4)
C10—C1—C6118.8 (5)C11—C12—H12A108.7
C10—C9—C8122.4 (6)Br1—C12—H12A108.7
C10—C9—H9118.8C11—C12—H12B108.7
C8—C9—H9118.8Br1—C12—H12B108.7
C3—C2—C1122.1 (7)H12A—C12—H12B107.6
C7—C8—C11—O13.4 (10)C7—C6—C1—C100.3 (10)
C9—C8—C11—O1176.8 (6)C7—C8—C9—C100.2 (10)
C7—C8—C11—C12175.2 (6)C11—C8—C9—C10179.5 (6)
C9—C8—C11—C124.6 (9)C10—C1—C2—C3180.0 (7)
C9—C8—C7—O2178.4 (6)C6—C1—C2—C30.2 (11)
C11—C8—C7—O21.8 (9)C8—C9—C10—C10.0 (11)
C9—C8—C7—C60.5 (10)C2—C1—C10—C9179.8 (7)
C11—C8—C7—C6179.3 (6)C6—C1—C10—C90.0 (10)
O2—C7—C6—C50.9 (10)C1—C2—C3—C41.0 (13)
C8—C7—C6—C5179.9 (7)C2—C3—C4—C51.8 (14)
O2—C7—C6—C1178.5 (6)C3—C4—C5—C61.5 (12)
C8—C7—C6—C10.6 (10)C7—C6—C5—C4179.0 (7)
C5—C6—C1—C20.5 (10)C1—C6—C5—C40.3 (11)
C7—C6—C1—C2179.9 (7)O1—C11—C12—Br12.7 (9)
C5—C6—C1—C10179.7 (6)C8—C11—C12—Br1175.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12B···O1i0.972.533.265 (8)132
O2—H2O···O10.821.832.559 (6)147
Symmetry code: (i) x1, y+1/2, z+1/2.
 

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