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The molecule of the title compound, C6H6BrNO, is essentially planar. Inter­molecular O—H...Br hydrogen bonds link the mol­ecules into a chain along [101].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015066/ci2059sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015066/ci2059Isup2.hkl
Contains datablock I

CCDC reference: 608588

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.015 Å
  • R factor = 0.056
  • wR factor = 0.142
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.79 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 15
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 0.789 Tmax scaled 0.297 Tmin scaled 0.208 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.96 From the CIF: _reflns_number_total 1294 Count of symmetry unique reflns 690 Completeness (_total/calc) 187.54% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 604 Fraction of Friedel pairs measured 0.875 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

5-Bromo-2-(hydroxymethyl)pyridine top
Crystal data top
C6H6BrNOF(000) = 184
Mr = 188.03Dx = 1.870 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 4.039 (1) Åθ = 9–13°
b = 8.974 (2) ŵ = 6.07 mm1
c = 9.224 (2) ÅT = 293 K
β = 93.09 (3)°Block, brown
V = 333.85 (13) Å30.30 × 0.20 × 0.20 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
1093 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 26.0°, θmin = 2.2°
ω/2θ scansh = 04
Absorption correction: ψ scan
(North et al., 1968)
k = 1111
Tmin = 0.263, Tmax = 0.377l = 1111
1479 measured reflections3 standard reflections every 200 reflections
1294 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.142 w = 1/[σ2(Fo2) + (0.0999P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
1294 reflectionsΔρmax = 0.52 e Å3
82 parametersΔρmin = 0.77 e Å3
1 restraintAbsolute structure: Flack (1983), with 601 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (3)
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.

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
Br10.1262 (2)0.25210 (17)0.40114 (7)0.0479 (3)
O10.8828 (17)0.1474 (10)1.0727 (7)0.062 (2)
H10.94360.15651.15850.093*
N10.380 (2)0.3728 (8)0.8225 (8)0.0431 (18)
C10.3050 (17)0.250 (2)0.5959 (7)0.0365 (16)
C20.260 (2)0.3691 (9)0.6842 (10)0.0398 (19)
H20.14170.45080.64720.048*
C30.5450 (16)0.256 (2)0.8743 (7)0.0360 (15)
C40.598 (2)0.1308 (10)0.7885 (10)0.042 (2)
H40.71650.04960.82680.051*
C50.474 (3)0.1291 (9)0.6467 (10)0.0380 (18)
H50.50510.04700.58740.046*
C60.669 (2)0.265 (3)1.0320 (9)0.050 (3)
H6A0.78480.35831.04840.060*
H6B0.48110.26311.09290.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0616 (5)0.0467 (5)0.0343 (4)0.0141 (7)0.0067 (3)0.0037 (8)
O10.068 (5)0.071 (5)0.045 (4)0.009 (4)0.021 (4)0.018 (4)
N10.064 (5)0.031 (4)0.034 (4)0.003 (4)0.002 (4)0.003 (3)
C10.045 (4)0.033 (4)0.031 (3)0.008 (8)0.004 (3)0.017 (7)
C20.053 (6)0.027 (4)0.039 (5)0.002 (4)0.003 (4)0.002 (3)
C30.035 (3)0.040 (4)0.034 (3)0.011 (8)0.006 (3)0.002 (8)
C40.055 (6)0.032 (5)0.041 (5)0.012 (4)0.010 (4)0.005 (4)
C50.049 (5)0.030 (4)0.036 (5)0.003 (4)0.005 (4)0.005 (4)
C60.060 (5)0.058 (7)0.030 (4)0.015 (7)0.003 (3)0.007 (7)
Geometric parameters (Å, º) top
Br1—C11.900 (7)C3—C41.397 (19)
O1—C61.397 (19)C3—C61.515 (10)
O1—H10.82C4—C51.376 (13)
N1—C31.318 (19)C4—H40.93
N1—C21.341 (12)C5—H50.93
C1—C51.354 (18)C6—H6A0.97
C1—C21.359 (17)C6—H6B0.97
C2—H20.93
C6—O1—H1109.5C5—C4—H4120.4
C3—N1—C2118.3 (8)C3—C4—H4120.4
C5—C1—C2120.2 (7)C1—C5—C4118.1 (8)
C5—C1—Br1119.5 (9)C1—C5—H5120.9
C2—C1—Br1120.2 (11)C4—C5—H5120.9
N1—C2—C1122.5 (9)O1—C6—C3112.8 (14)
N1—C2—H2118.8O1—C6—H6A109.0
C1—C2—H2118.8C3—C6—H6A109.0
N1—C3—C4121.6 (7)O1—C6—H6B109.0
N1—C3—C6116.2 (15)C3—C6—H6B109.0
C4—C3—C6122.1 (15)H6A—C6—H6B107.8
C5—C4—C3119.2 (9)
C3—N1—C2—C10.6 (15)C6—C3—C4—C5178.9 (10)
C5—C1—C2—N10.5 (16)C2—C1—C5—C40.4 (15)
Br1—C1—C2—N1179.7 (7)Br1—C1—C5—C4179.5 (7)
C2—N1—C3—C40.5 (15)C3—C4—C5—C10.3 (14)
C2—N1—C3—C6178.8 (9)N1—C3—C6—O1171.0 (9)
N1—C3—C4—C50.4 (15)C4—C3—C6—O19.7 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Br1i0.822.473.272 (7)165
C4—H4···O10.932.492.809 (11)100
Symmetry code: (i) x+1, y, z+1.
 

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