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The mol­ecule of the title compound, C6H4BrNO, is essentially planar. In the crystal structure, C—H...N hydrogen bonds link the mol­ecules into a chain along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011615/ci2041sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011615/ci2041Isup2.hkl
Contains datablock I

CCDC reference: 608389

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.038
  • wR factor = 0.099
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 4 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
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 1 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: DIFRAC (Gabe et al., 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

6-Bromopyridine-2-carbaldehyde top
Crystal data top
C6H4BrNOF(000) = 360
Mr = 186.00Dx = 1.897 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yabCell parameters from 22 reflections
a = 6.908 (2) Åθ = 4.4–7.7°
b = 6.290 (4) ŵ = 6.22 mm1
c = 15.060 (6) ÅT = 290 K
β = 95.57 (3)°Block, yellow
V = 651.3 (5) Å30.24 × 0.22 × 0.22 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.012
Radiation source: fine-focus sealed tubeθmax = 25.4°, θmin = 1.4°
Graphite monochromatorh = 88
ω/2θ scansk = 07
1335 measured reflectionsl = 818
1202 independent reflections3 standard reflections every 200 reflections
750 reflections with I > 2σ(I) intensity decay: 1.3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038All H-atom parameters refined
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.056P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
1202 reflectionsΔρmax = 0.34 e Å3
99 parametersΔρmin = 0.44 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.037 (4)
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
Br10.82162 (10)0.08760 (10)0.58233 (3)0.0649 (3)
O10.8667 (6)0.2360 (7)0.9935 (2)0.0658 (11)
N10.8400 (6)0.1588 (6)0.7622 (3)0.0406 (10)
C10.8355 (7)0.2589 (9)0.6868 (3)0.0460 (12)
C20.8413 (9)0.4787 (8)0.6781 (4)0.0509 (14)
C30.8510 (9)0.5974 (8)0.7545 (4)0.0536 (13)
C40.8564 (8)0.4960 (8)0.8347 (3)0.0463 (13)
C50.8496 (7)0.2775 (7)0.8364 (3)0.0379 (11)
C60.8541 (9)0.1550 (8)0.9205 (4)0.0513 (14)
H20.850 (7)0.542 (8)0.625 (3)0.051 (14)*
H30.852 (7)0.760 (9)0.746 (3)0.053 (14)*
H40.867 (8)0.586 (8)0.893 (2)0.072 (17)*
H60.851 (8)0.008 (10)0.906 (4)0.072 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0928 (5)0.0614 (4)0.0395 (3)0.0033 (4)0.0009 (3)0.0134 (3)
O10.093 (3)0.064 (2)0.0395 (19)0.001 (2)0.0046 (19)0.001 (2)
N10.051 (2)0.034 (2)0.037 (2)0.0002 (18)0.0013 (18)0.0016 (17)
C10.053 (3)0.041 (3)0.042 (3)0.002 (3)0.002 (2)0.012 (2)
C20.071 (4)0.038 (3)0.044 (3)0.004 (3)0.006 (3)0.009 (2)
C30.077 (4)0.035 (3)0.049 (3)0.004 (3)0.005 (3)0.004 (3)
C40.059 (3)0.034 (2)0.046 (3)0.004 (3)0.001 (3)0.008 (2)
C50.046 (3)0.032 (2)0.034 (2)0.003 (2)0.001 (2)0.001 (2)
C60.068 (4)0.041 (3)0.044 (3)0.003 (3)0.001 (3)0.001 (2)
Geometric parameters (Å, º) top
Br1—C11.901 (5)C3—C41.364 (7)
O1—C61.207 (6)C3—H31.03 (5)
N1—C11.296 (6)C4—C51.376 (7)
N1—C51.341 (6)C4—H41.04 (4)
C1—C21.390 (8)C5—C61.481 (7)
C2—C31.368 (7)C6—H61.05 (6)
C2—H20.91 (5)
C1—N1—C5117.1 (4)C3—C4—C5119.0 (5)
N1—C1—C2124.6 (4)C3—C4—H4119 (3)
N1—C1—Br1116.4 (4)C5—C4—H4122 (3)
C2—C1—Br1119.0 (4)N1—C5—C4122.7 (4)
C3—C2—C1117.6 (5)N1—C5—C6114.8 (4)
C3—C2—H2120 (3)C4—C5—C6122.5 (4)
C1—C2—H2122 (3)O1—C6—C5123.6 (5)
C4—C3—C2119.0 (5)O1—C6—H6127 (3)
C4—C3—H3125 (3)C5—C6—H6110 (3)
C2—C3—H3116 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N1i1.03 (6)2.52 (6)3.534 (7)167 (4)
Symmetry code: (i) x, y+1, z.
 

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