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The molecule of the title compound, C13H10Br2N2O, is nearly planar and displays a trans configuration with respect to the central C=N double bond. In the crystal structure, the mol­ecules are linked through inter­molecular C—H...Br hydrogen bonds, forming chains running along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008580/bh2008sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008580/bh2008Isup2.hkl
Contains datablock I

CCDC reference: 604967

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.035
  • wR factor = 0.075
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. N2 .. 3.24 Ang.
Alert level G 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 26.50 From the CIF: _reflns_number_total 2617 Count of symmetry unique reflns 1420 Completeness (_total/calc) 184.30% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1197 Fraction of Friedel pairs measured 0.843 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

2,4-Dibromo-6-(4-methylpyridin-2-yliminomethyl)phenol top
Crystal data top
C13H10Br2N2OF(000) = 360
Mr = 370.05Dx = 1.869 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1653 reflections
a = 6.077 (1) Åθ = 2.5–24.1°
b = 14.224 (2) ŵ = 6.15 mm1
c = 7.676 (1) ÅT = 298 K
β = 97.791 (2)°Block, yellow
V = 657.38 (17) Å30.20 × 0.20 × 0.19 mm
Z = 2
Data collection top
Bruker APEX area-detector
diffractometer
2617 independent reflections
Radiation source: fine-focus sealed tube2111 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 26.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 77
Tmin = 0.298, Tmax = 0.310k = 1717
5325 measured reflectionsl = 99
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)] = 0.035H-atom parameters constrained
wR(F2) = 0.075 w = 1/[σ2(Fo2) + (0.0257P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2617 reflectionsΔρmax = 0.39 e Å3
166 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: 0.389 (12), 1197 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: Flack (1983)
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
Br11.35666 (9)0.97782 (3)0.73700 (8)0.06337 (18)
Br21.50915 (10)0.58820 (3)0.79446 (8)0.0678 (2)
O10.9168 (6)0.9128 (2)0.5442 (5)0.0566 (9)
H10.79660.89410.49490.085*
N10.6307 (7)0.7910 (3)0.3945 (5)0.0437 (10)
N20.3830 (7)0.6767 (3)0.2523 (6)0.0570 (12)
C10.9735 (7)0.7456 (3)0.5627 (6)0.0389 (11)
C21.0435 (8)0.8395 (3)0.5993 (6)0.0399 (11)
C31.2516 (8)0.8536 (3)0.6955 (6)0.0408 (11)
C41.3888 (8)0.7796 (4)0.7537 (6)0.0440 (12)
H41.52810.79060.81680.053*
C51.3156 (8)0.6884 (3)0.7164 (6)0.0435 (11)
C61.1133 (8)0.6704 (3)0.6221 (6)0.0432 (11)
H61.06830.60880.59740.052*
C70.7626 (8)0.7265 (3)0.4553 (6)0.0451 (12)
H70.72290.66430.43030.054*
C80.4273 (9)0.7670 (3)0.2901 (7)0.0419 (11)
C90.2835 (8)0.8386 (4)0.2342 (6)0.0454 (11)
H90.32260.90030.26470.054*
C100.0825 (8)0.8209 (4)0.1335 (7)0.0501 (13)
C110.0376 (9)0.7271 (4)0.0959 (7)0.0585 (15)
H110.09640.71010.03030.070*
C120.1885 (9)0.6599 (4)0.1544 (7)0.0622 (15)
H120.15370.59780.12410.075*
C130.0751 (10)0.8978 (4)0.0703 (8)0.0696 (17)
H13A0.03480.95410.13610.104*
H13B0.22320.87970.08610.104*
H13C0.06860.90930.05220.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0593 (3)0.0380 (3)0.0848 (4)0.0060 (2)0.0192 (3)0.0053 (3)
Br20.0616 (4)0.0452 (3)0.0911 (4)0.0110 (3)0.0095 (3)0.0107 (3)
O10.046 (2)0.0387 (18)0.078 (3)0.0044 (16)0.0163 (18)0.0031 (17)
N10.038 (2)0.045 (2)0.048 (3)0.0012 (19)0.0024 (19)0.0029 (19)
N20.046 (3)0.050 (3)0.072 (3)0.001 (2)0.007 (2)0.011 (2)
C10.038 (3)0.042 (3)0.036 (3)0.005 (2)0.002 (2)0.0023 (19)
C20.041 (3)0.036 (2)0.041 (3)0.000 (2)0.001 (2)0.001 (2)
C30.042 (3)0.031 (3)0.047 (3)0.004 (2)0.000 (2)0.007 (2)
C40.042 (3)0.046 (3)0.042 (3)0.001 (2)0.001 (2)0.004 (2)
C50.041 (3)0.040 (3)0.048 (3)0.004 (2)0.001 (2)0.005 (2)
C60.050 (3)0.031 (3)0.048 (3)0.003 (2)0.005 (2)0.000 (2)
C70.045 (3)0.045 (3)0.044 (3)0.005 (2)0.003 (2)0.002 (2)
C80.039 (2)0.040 (3)0.047 (3)0.006 (2)0.003 (2)0.004 (2)
C90.042 (3)0.042 (3)0.051 (3)0.005 (2)0.001 (2)0.003 (2)
C100.042 (3)0.061 (3)0.046 (3)0.004 (2)0.005 (2)0.003 (2)
C110.044 (3)0.073 (4)0.058 (4)0.010 (3)0.001 (3)0.014 (3)
C120.054 (3)0.052 (3)0.076 (4)0.005 (3)0.008 (3)0.016 (3)
C130.062 (4)0.072 (4)0.070 (4)0.014 (3)0.007 (3)0.020 (3)
Geometric parameters (Å, º) top
Br1—C31.891 (4)C5—C61.364 (6)
Br2—C51.893 (5)C6—H60.9300
O1—C21.330 (5)C7—H70.9300
O1—H10.8200C8—C91.372 (8)
N1—C71.265 (6)C9—C101.378 (7)
N1—C81.420 (6)C9—H90.9300
N2—C121.334 (6)C10—C111.383 (8)
N2—C81.336 (6)C10—C131.492 (7)
C1—C61.403 (6)C11—C121.359 (8)
C1—C21.418 (6)C11—H110.9300
C1—C71.452 (7)C12—H120.9300
C2—C31.390 (6)C13—H13A0.9600
C3—C41.379 (7)C13—H13B0.9600
C4—C51.388 (7)C13—H13C0.9600
C4—H40.9300
C2—O1—H1109.5C1—C7—H7118.7
C7—N1—C8119.6 (4)N2—C8—C9123.0 (5)
C12—N2—C8115.6 (5)N2—C8—N1119.2 (5)
C6—C1—C2120.1 (4)C9—C8—N1117.8 (5)
C6—C1—C7119.3 (4)C8—C9—C10121.2 (5)
C2—C1—C7120.5 (4)C8—C9—H9119.4
O1—C2—C3120.1 (4)C10—C9—H9119.4
O1—C2—C1122.0 (4)C9—C10—C11115.4 (5)
C3—C2—C1117.9 (4)C9—C10—C13122.0 (5)
C4—C3—C2122.0 (4)C11—C10—C13122.7 (5)
C4—C3—Br1118.9 (3)C12—C11—C10120.3 (5)
C2—C3—Br1119.1 (3)C12—C11—H11119.9
C3—C4—C5118.9 (4)C10—C11—H11119.9
C3—C4—H4120.6N2—C12—C11124.5 (5)
C5—C4—H4120.6N2—C12—H12117.7
C6—C5—C4121.7 (4)C11—C12—H12117.7
C6—C5—Br2120.2 (4)C10—C13—H13A109.5
C4—C5—Br2118.0 (4)C10—C13—H13B109.5
C5—C6—C1119.5 (4)H13A—C13—H13B109.5
C5—C6—H6120.3C10—C13—H13C109.5
C1—C6—H6120.3H13A—C13—H13C109.5
N1—C7—C1122.7 (5)H13B—C13—H13C109.5
N1—C7—H7118.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···Br2i0.932.923.783 (5)155
O1—H1···N10.821.882.608 (5)147
C7—H7···N20.932.322.698 (5)104
Symmetry code: (i) x+2, y+1/2, z+1.
 

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