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The mol­ecule of the title compound, C13H10BrN3O2, is approximately planar and displays a trans configuration with respect to the C=N double bond. The crystal structure is stabilized by inter­molecular N—H...N hydrogen bonds, forming layers parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030765/hg2091sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030765/hg2091Isup2.hkl
Contains datablock I

CCDC reference: 621351

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.096
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O2 .. 3.12 Ang.
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 0.939 Tmax scaled 0.554 Tmin scaled 0.442
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 0 ALERT type 5 Informative message, check

Computing details top

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

N'-[1-(5-Bromo-2-hydroxyphenyl)methylidene]isonicotinohydrazide top
Crystal data top
C13H10BrN3O2F(000) = 640
Mr = 320.15Dx = 1.698 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1696 reflections
a = 8.563 (1) Åθ = 2.5–23.7°
b = 15.875 (2) ŵ = 3.28 mm1
c = 9.368 (2) ÅT = 298 K
β = 100.448 (2)°Block, yellow
V = 1252.4 (3) Å30.27 × 0.23 × 0.18 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2857 independent reflections
Radiation source: fine-focus sealed tube1872 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.471, Tmax = 0.590k = 1920
10587 measured reflectionsl = 1212
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0213P)2 + 0.3987P]
where P = (Fo2 + 2Fc2)/3
2857 reflections(Δ/σ)max = 0.001
176 parametersΔρmax = 0.42 e Å3
1 restraintΔρmin = 0.31 e Å3
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
Br10.30155 (4)1.09897 (3)0.04449 (4)0.05402 (16)
O10.7279 (3)1.13591 (16)0.6250 (2)0.0523 (7)
H10.78511.09450.64450.079*
O21.0534 (3)1.00635 (15)0.8128 (3)0.0574 (7)
N10.8347 (3)0.98735 (17)0.5852 (3)0.0358 (6)
N20.9289 (3)0.92064 (16)0.6384 (3)0.0365 (7)
N31.3330 (3)0.73731 (18)0.9628 (3)0.0380 (7)
C10.6338 (4)1.04986 (19)0.4144 (3)0.0325 (7)
C20.6333 (4)1.1248 (2)0.4943 (3)0.0344 (7)
C30.5330 (4)1.1893 (2)0.4397 (4)0.0420 (8)
H30.53001.23790.49460.050*
C40.4367 (4)1.1834 (2)0.3051 (4)0.0398 (8)
H40.37181.22820.26780.048*
C50.4381 (4)1.11012 (19)0.2268 (3)0.0341 (7)
C60.5332 (4)1.0437 (2)0.2794 (3)0.0361 (8)
H60.53090.99440.22540.043*
C70.7353 (4)0.9793 (2)0.4677 (3)0.0364 (8)
H70.72770.92880.41660.044*
C81.0367 (4)0.9371 (2)0.7597 (3)0.0374 (8)
C91.1350 (4)0.8634 (2)0.8258 (3)0.0334 (7)
C101.2054 (4)0.8705 (2)0.9705 (3)0.0388 (8)
H101.18740.91771.02410.047*
C111.3020 (4)0.8066 (2)1.0336 (3)0.0401 (8)
H111.34840.81191.13100.048*
C121.2653 (4)0.7326 (2)0.8234 (3)0.0397 (8)
H121.28700.68550.77140.048*
C131.1651 (4)0.7928 (2)0.7513 (3)0.0362 (8)
H131.11900.78560.65430.043*
H20.911 (5)0.8703 (13)0.595 (4)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0534 (3)0.0584 (3)0.0414 (2)0.0031 (2)0.01487 (17)0.00346 (19)
O10.0681 (18)0.0455 (15)0.0360 (14)0.0103 (13)0.0102 (12)0.0088 (12)
O20.0693 (18)0.0366 (14)0.0540 (16)0.0059 (13)0.0215 (14)0.0055 (12)
N10.0362 (15)0.0365 (16)0.0309 (14)0.0038 (12)0.0043 (12)0.0045 (12)
N20.0368 (16)0.0312 (15)0.0367 (16)0.0019 (12)0.0060 (13)0.0043 (12)
N30.0360 (16)0.0431 (17)0.0334 (15)0.0019 (13)0.0026 (12)0.0055 (13)
C10.0335 (17)0.0320 (18)0.0309 (16)0.0026 (14)0.0031 (14)0.0033 (14)
C20.0379 (18)0.0372 (18)0.0267 (16)0.0022 (14)0.0024 (14)0.0012 (14)
C30.051 (2)0.0317 (18)0.043 (2)0.0058 (16)0.0066 (17)0.0039 (15)
C40.0403 (19)0.037 (2)0.042 (2)0.0053 (15)0.0087 (16)0.0053 (16)
C50.0346 (18)0.0353 (18)0.0300 (17)0.0018 (14)0.0003 (14)0.0063 (14)
C60.0388 (19)0.0329 (18)0.0341 (17)0.0030 (15)0.0004 (15)0.0019 (15)
C70.0397 (19)0.0288 (18)0.0382 (19)0.0017 (14)0.0004 (16)0.0027 (14)
C80.0392 (19)0.0338 (18)0.0362 (19)0.0001 (15)0.0015 (15)0.0021 (15)
C90.0318 (17)0.0333 (17)0.0314 (18)0.0046 (14)0.0039 (14)0.0078 (14)
C100.048 (2)0.0346 (18)0.0313 (18)0.0034 (16)0.0000 (16)0.0000 (14)
C110.0409 (19)0.045 (2)0.0309 (18)0.0047 (16)0.0035 (15)0.0083 (16)
C120.045 (2)0.0356 (19)0.0374 (19)0.0002 (16)0.0049 (16)0.0026 (15)
C130.0357 (18)0.0397 (19)0.0299 (17)0.0049 (15)0.0029 (14)0.0023 (15)
Geometric parameters (Å, º) top
Br1—C51.895 (3)C3—H30.9300
O1—C21.352 (4)C4—C51.377 (4)
O1—H10.8200C4—H40.9300
O2—C81.205 (4)C5—C61.368 (4)
N1—C71.269 (4)C6—H60.9300
N1—N21.369 (3)C7—H70.9300
N2—C81.354 (4)C8—C91.507 (4)
N2—H20.895 (10)C9—C131.370 (4)
N3—C121.331 (4)C9—C101.384 (4)
N3—C111.336 (4)C10—C111.373 (4)
C1—C61.398 (4)C10—H100.9300
C1—C21.406 (4)C11—H110.9300
C1—C71.450 (4)C12—C131.377 (4)
C2—C31.374 (4)C12—H120.9300
C3—C41.379 (4)C13—H130.9300
C2—O1—H1109.5C1—C6—H6120.0
C7—N1—N2119.7 (3)N1—C7—C1119.1 (3)
C8—N2—N1115.1 (3)N1—C7—H7120.4
C8—N2—H2126 (3)C1—C7—H7120.4
N1—N2—H2119 (3)O2—C8—N2122.3 (3)
C12—N3—C11116.3 (3)O2—C8—C9121.6 (3)
C6—C1—C2118.6 (3)N2—C8—C9116.2 (3)
C6—C1—C7119.4 (3)C13—C9—C10118.5 (3)
C2—C1—C7122.0 (3)C13—C9—C8124.6 (3)
O1—C2—C3118.1 (3)C10—C9—C8116.8 (3)
O1—C2—C1122.2 (3)C11—C10—C9118.9 (3)
C3—C2—C1119.7 (3)C11—C10—H10120.5
C2—C3—C4121.3 (3)C9—C10—H10120.5
C2—C3—H3119.4N3—C11—C10123.5 (3)
C4—C3—H3119.4N3—C11—H11118.2
C5—C4—C3118.9 (3)C10—C11—H11118.2
C5—C4—H4120.5N3—C12—C13124.3 (3)
C3—C4—H4120.5N3—C12—H12117.8
C6—C5—C4121.4 (3)C13—C12—H12117.8
C6—C5—Br1118.9 (2)C9—C13—C12118.4 (3)
C4—C5—Br1119.7 (2)C9—C13—H13120.8
C5—C6—C1120.1 (3)C12—C13—H13120.8
C5—C6—H6120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.581 (4)146
N2—H2···N3i0.90 (1)2.14 (3)3.029 (4)169 (4)
Symmetry code: (i) x1/2, y+3/2, z1/2.
 

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