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In the solid state, the title mol­ecule, C13H10BrNO2, exhibits two intra­molecular hydrogen bonds, namely an O—H...O hydrogen bond between vicinal hydr­oxy groups and an N—H...O hydrogen bond involving hydr­oxy and imine groups. In the crystal structure, symmetry-related mol­ecules are linked by bifurcated O—H...O hydrogen bonds to form centrosymmetric hydrogen-bonded dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039183/kp2053sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039183/kp2053Isup2.hkl
Contains datablock I

CCDC reference: 627968

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.032
  • wR factor = 0.076
  • Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

3-(4-Bromophenyliminomethyl)benzene-1,2-diol top
Crystal data top
C13H10BrNO2Z = 2
Mr = 292.13F(000) = 292
Triclinic, P1Dx = 1.665 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.0312 (12) ÅCell parameters from 7425 reflections
b = 8.7087 (15) Åθ = 1.7–29.6°
c = 11.837 (2) ŵ = 3.51 mm1
α = 87.234 (15)°T = 173 K
β = 81.945 (15)°Plate, orange-red
γ = 71.189 (14)°0.41 × 0.35 × 0.21 mm
V = 582.71 (19) Å3
Data collection top
Stoe IPDS-2
diffractometer
3121 independent reflections
Radiation source: fine-focus sealed tube2733 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 6.67 pixels mm-1θmax = 29.2°, θmin = 1.7°
φ and ω scansh = 88
Absorption correction: integration
(X-RED32; Stoe & Cie, 2006)
k = 1111
Tmin = 0.269, Tmax = 0.500l = 1616
7421 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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0257P)2 + 0.6141P]
where P = (Fo2 + 2Fc2)/3
3121 reflections(Δ/σ)max = 0.001
156 parametersΔρmax = 0.85 e Å3
0 restraintsΔρmin = 0.77 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Br10.18618 (5)0.37185 (3)0.94410 (2)0.0402 (1)
O10.3014 (2)0.46724 (17)0.60514 (13)0.0246 (4)
O20.2511 (2)0.74287 (18)0.47649 (13)0.0279 (4)
N10.1008 (3)0.2933 (2)0.73726 (14)0.0236 (5)
C10.1524 (4)0.1606 (2)0.88345 (17)0.0266 (5)
C20.0254 (4)0.0908 (2)0.81691 (18)0.0265 (6)
C30.0466 (4)0.0615 (2)0.76946 (17)0.0252 (5)
C40.1092 (3)0.1422 (2)0.78856 (16)0.0223 (5)
C50.2901 (4)0.0681 (3)0.85422 (18)0.0275 (6)
C60.3105 (4)0.0833 (3)0.90279 (18)0.0294 (6)
C70.0998 (3)0.4043 (2)0.73342 (17)0.0235 (5)
C80.1171 (3)0.5547 (2)0.67180 (16)0.0219 (5)
C90.0834 (3)0.5785 (2)0.60771 (16)0.0203 (5)
C100.0607 (3)0.7199 (2)0.54292 (16)0.0216 (5)
C110.1575 (3)0.8386 (2)0.54499 (17)0.0245 (5)
C120.3562 (4)0.8171 (3)0.61025 (19)0.0274 (5)
C130.3369 (3)0.6757 (2)0.67184 (18)0.0254 (5)
H10.292800.387600.646400.0370*
H20.372000.663200.483700.0420*
H2A0.131700.146300.803800.0320*
H3A0.168300.110700.723700.0300*
H5A0.399800.121600.865700.0330*
H6A0.431700.133000.948700.0350*
H7A0.239200.387200.771700.0280*
H11A0.171800.935200.501600.0290*
H12A0.505000.899800.612400.0330*
H13A0.473700.660300.714600.0300*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0560 (2)0.0233 (1)0.0350 (1)0.0075 (1)0.0006 (1)0.0091 (1)
O10.0191 (6)0.0191 (6)0.0320 (7)0.0037 (5)0.0003 (5)0.0064 (5)
O20.0220 (7)0.0229 (7)0.0369 (8)0.0067 (5)0.0025 (6)0.0110 (6)
N10.0262 (8)0.0220 (8)0.0231 (8)0.0093 (6)0.0009 (6)0.0008 (6)
C10.0336 (10)0.0184 (8)0.0227 (9)0.0044 (7)0.0021 (7)0.0042 (7)
C20.0312 (10)0.0228 (9)0.0270 (10)0.0117 (8)0.0025 (8)0.0034 (7)
C30.0275 (9)0.0233 (9)0.0256 (9)0.0092 (8)0.0048 (7)0.0043 (7)
C40.0247 (9)0.0205 (8)0.0198 (8)0.0063 (7)0.0006 (7)0.0002 (7)
C50.0270 (9)0.0285 (10)0.0282 (10)0.0100 (8)0.0054 (8)0.0008 (8)
C60.0302 (10)0.0274 (10)0.0266 (10)0.0031 (8)0.0069 (8)0.0037 (8)
C70.0247 (9)0.0233 (9)0.0228 (9)0.0097 (7)0.0009 (7)0.0006 (7)
C80.0232 (9)0.0198 (8)0.0226 (9)0.0073 (7)0.0010 (7)0.0017 (7)
C90.0204 (8)0.0175 (8)0.0223 (8)0.0048 (7)0.0032 (7)0.0000 (6)
C100.0225 (8)0.0194 (8)0.0240 (9)0.0078 (7)0.0042 (7)0.0016 (7)
C110.0272 (9)0.0189 (8)0.0278 (10)0.0063 (7)0.0080 (7)0.0025 (7)
C120.0225 (9)0.0236 (9)0.0328 (10)0.0020 (7)0.0053 (8)0.0024 (8)
C130.0211 (9)0.0260 (9)0.0270 (9)0.0057 (7)0.0003 (7)0.0034 (8)
Geometric parameters (Å, º) top
Br1—C11.9009 (18)C8—C131.402 (3)
O1—C91.356 (2)C8—C91.404 (3)
O2—C101.363 (2)C9—C101.397 (2)
O1—H10.8400C10—C111.385 (3)
O2—H20.8400C11—C121.393 (3)
N1—C71.287 (3)C12—C131.381 (3)
N1—C41.411 (2)C2—H2A0.9500
C1—C61.380 (3)C3—H3A0.9500
C1—C21.382 (3)C5—H5A0.9500
C2—C31.389 (2)C6—H6A0.9500
C3—C41.389 (3)C7—H7A0.9500
C4—C51.395 (3)C11—H11A0.9500
C5—C61.388 (3)C12—H12A0.9500
C7—C81.449 (2)C13—H13A0.9500
Br1···Br1i3.7271 (8)C7···H3A2.7300
Br1···C4ii3.731 (2)C7···H12.4100
Br1···H13Aiii3.2300C8···H2Aix3.0700
O1···O22.735 (2)C12···H2x3.0000
O1···N12.574 (2)C12···H2Aix2.9000
O1···O2iv2.797 (2)C13···H2x3.0500
O2···C7v3.217 (3)C13···H2Aix2.9000
O2···O12.735 (2)H1···N11.8300
O2···O1iv2.797 (2)H1···C43.0500
O2···C12vi3.267 (3)H1···C72.4100
O1···H13Avi2.9200H1···O2iv2.8300
O1···H2iv2.0900H1···H2iv2.3000
O1···H22.2800H2···O12.2800
O2···H1iv2.8300H2···C12vi3.0000
O2···H3Av2.6700H2···C13vi3.0500
O2···H11Avii2.7100H2···O1iv2.0900
N1···O12.574 (2)H2···H1iv2.3000
N1···H11.8300H2A···C8viii3.0700
C2···C11viii3.549 (3)H2A···C12viii2.9000
C4···Br1ii3.731 (2)H2A···C13viii2.9000
C6···C13iii3.528 (3)H3A···C72.7300
C7···C10v3.448 (3)H3A···H7A2.3900
C7···O2v3.217 (3)H3A···O2v2.6700
C8···C10v3.481 (3)H5A···H6Axii2.5700
C8···C9v3.516 (3)H6A···H5Axii2.5700
C9···C8v3.516 (3)H7A···C32.7000
C9···C9v3.365 (3)H7A···H3A2.3900
C10···C7v3.448 (3)H7A···H13A2.4600
C10···C8v3.481 (3)H11A···O2vii2.7100
C11···C2ix3.549 (3)H11A···H12Axiii2.5400
C12···O2x3.267 (3)H12A···H11Axiii2.5400
C13···C6xi3.528 (3)H13A···Br1xi3.2300
C1···H13Aiii2.8800H13A···O1x2.9200
C3···H7A2.7000H13A···C1xi2.8800
C4···H13.0500H13A···C6xi3.0700
C6···H13Aiii3.0700H13A···H7A2.4600
C9—O1—H1109.00C9—C10—C11120.10 (17)
C10—O2—H2109.00O2—C10—C9120.86 (16)
C4—N1—C7119.84 (18)C10—C11—C12120.35 (18)
Br1—C1—C2118.80 (16)C11—C12—C13120.0 (2)
C2—C1—C6121.55 (18)C8—C13—C12120.55 (19)
Br1—C1—C6119.60 (17)C1—C2—H2A120.00
C1—C2—C3119.1 (2)C3—C2—H2A120.00
C2—C3—C4120.4 (2)C2—C3—H3A120.00
C3—C4—C5119.55 (18)C4—C3—H3A120.00
N1—C4—C3122.03 (17)C4—C5—H5A120.00
N1—C4—C5118.29 (18)C6—C5—H5A120.00
C4—C5—C6120.3 (2)C1—C6—H6A120.00
C1—C6—C5119.1 (2)C5—C6—H6A120.00
N1—C7—C8121.32 (18)N1—C7—H7A119.00
C7—C8—C13120.17 (17)C8—C7—H7A119.00
C7—C8—C9120.58 (16)C10—C11—H11A120.00
C9—C8—C13119.20 (16)C12—C11—H11A120.00
O1—C9—C10118.07 (17)C11—C12—H12A120.00
O1—C9—C8122.14 (16)C13—C12—H12A120.00
C8—C9—C10119.78 (16)C8—C13—H13A120.00
O2—C10—C11119.04 (16)C12—C13—H13A120.00
C7—N1—C4—C343.4 (3)C7—C8—C9—O13.4 (3)
C7—N1—C4—C5140.9 (2)C7—C8—C9—C10175.87 (17)
C4—N1—C7—C8173.90 (17)C13—C8—C9—O1179.18 (17)
Br1—C1—C2—C3178.06 (16)C13—C8—C9—C101.5 (3)
C6—C1—C2—C30.7 (3)C7—C8—C13—C12177.83 (19)
Br1—C1—C6—C5177.38 (17)C9—C8—C13—C120.4 (3)
C2—C1—C6—C50.0 (3)O1—C9—C10—O21.9 (3)
C1—C2—C3—C40.1 (3)O1—C9—C10—C11178.50 (17)
C2—C3—C4—N1176.77 (18)C8—C9—C10—O2177.39 (17)
C2—C3—C4—C51.1 (3)C8—C9—C10—C112.2 (3)
N1—C4—C5—C6177.61 (19)O2—C10—C11—C12178.70 (18)
C3—C4—C5—C61.8 (3)C9—C10—C11—C120.9 (3)
C4—C5—C6—C11.2 (3)C10—C11—C12—C131.1 (3)
N1—C7—C8—C94.6 (3)C11—C12—C13—C81.7 (3)
N1—C7—C8—C13178.06 (19)
Symmetry codes: (i) x, y1, z+2; (ii) x, y, z+2; (iii) x+1, y1, z; (iv) x+1, y+1, z+1; (v) x, y+1, z+1; (vi) x+1, y, z; (vii) x, y+2, z+1; (viii) x, y1, z; (ix) x, y+1, z; (x) x1, y, z; (xi) x1, y+1, z; (xii) x+1, y, z+2; (xiii) x1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.842.282.735 (2)114
O1—H1···N10.841.832.574 (2)147
O2—H2···O1iv0.842.092.797 (2)141
Symmetry code: (iv) x+1, y+1, z+1.
 

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