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The title compound, C14H12N2O2, was isolated from the reaction between 4-methyl­phenyl­diazo­nium nitrite and salicyl­aldehyde in sodium hydro­xide. Structural analysis revealed a nearly planar mol­ecule with the aromatic rings in trans positions about the azo group. The molecular packing shows interdigitated stacks of 12-membered hydrogen-bonded dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013413/su6195sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013413/su6195Isup2.hkl
Contains datablock I

CCDC reference: 274648

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.046
  • wR factor = 0.102
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg. PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C1 .. 12.88 su PLAT230_ALERT_2_B Hirshfeld Test Diff for N2 - C7 .. 8.50 su
Alert level C PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit -P 21yc PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C13 .. 5.17 su PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C14 H12 N2 O2
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.

5-[(4-methylphenyl)diazenyl]salicylaldehyde top
Crystal data top
C14H12N2O2F(000) = 504
Mr = 240.26Dx = 1.358 Mg m3
Monoclinic, P21/cMelting point = 411–413 K
Hall symbol: -P 21ycMo Kα radiation, λ = 0.71069 Å
a = 21.578 (5) ÅCell parameters from 39 reflections
b = 4.674 (5) Åθ = 3.8–25.0°
c = 11.709 (5) ŵ = 0.09 mm1
β = 95.829 (5)°T = 293 K
V = 1174.8 (14) Å3Needle, brown
Z = 40.44 × 0.30 × 0.26 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.032
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.9°
Graphite monochromatorh = 2525
2θ/ω scansk = 15
2985 measured reflectionsl = 131
2061 independent reflections3 standard reflections every 97 reflections
1131 reflections with I > 2σ(I) 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)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.008P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.29(Δ/σ)max < 0.001
2061 reflectionsΔρmax = 0.24 e Å3
180 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0049 (6)
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
O10.41462 (7)0.3221 (4)0.39195 (14)0.0613 (6)
H10.44390.36240.43950.092*
O20.48213 (8)0.2907 (5)0.59592 (16)0.0787 (7)
N20.26054 (8)0.4860 (4)0.57034 (17)0.0482 (5)
C10.17764 (10)0.7766 (5)0.5509 (2)0.0418 (6)
C20.13061 (10)0.8871 (5)0.4755 (2)0.0488 (7)
H20.12710.82950.39910.059*
C30.08900 (10)1.0799 (5)0.5110 (2)0.0454 (6)
H30.05761.15110.45840.054*
C40.09269 (9)1.1716 (5)0.62447 (19)0.0379 (6)
C50.14068 (9)1.0620 (5)0.6999 (2)0.0431 (6)
H50.14451.12160.77610.052*
C60.18274 (10)0.8673 (5)0.6647 (2)0.0452 (6)
H60.21440.79660.71690.054*
C70.29931 (10)0.2789 (5)0.5195 (2)0.0430 (6)
C80.35071 (10)0.1848 (5)0.5871 (2)0.0467 (6)
H80.35880.25710.66110.056*
C90.39112 (9)0.0150 (5)0.54835 (19)0.0437 (6)
C100.37855 (10)0.1245 (5)0.4361 (2)0.0429 (6)
C110.32630 (9)0.0299 (5)0.3676 (2)0.0465 (6)
H110.31750.10230.29370.056*
C120.28782 (10)0.1687 (5)0.4081 (2)0.0475 (7)
H120.25330.23220.36090.057*
C130.44558 (12)0.1084 (7)0.6219 (3)0.0608 (8)
H130.4530 (10)0.001 (5)0.697 (2)0.073 (8)*
C140.04660 (13)1.3797 (7)0.6637 (3)0.0502 (7)
H14C0.0539 (13)1.560 (7)0.646 (3)0.103 (13)*
H14B0.0070 (14)1.346 (6)0.625 (3)0.103 (11)*
H14A0.0415 (12)1.366 (7)0.740 (3)0.107 (12)*
N10.21719 (8)0.5724 (4)0.50170 (17)0.0495 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0553 (10)0.0719 (13)0.0573 (11)0.0201 (10)0.0086 (9)0.0085 (11)
O20.0647 (12)0.0973 (16)0.0722 (13)0.0391 (12)0.0029 (10)0.0044 (13)
N20.0427 (10)0.0501 (13)0.0513 (12)0.0036 (11)0.0017 (10)0.0062 (11)
C10.0411 (13)0.0355 (14)0.0505 (15)0.0030 (11)0.0128 (11)0.0027 (13)
C20.0550 (14)0.0505 (16)0.0405 (14)0.0093 (13)0.0024 (12)0.0017 (13)
C30.0473 (13)0.0448 (15)0.0433 (14)0.0108 (12)0.0002 (11)0.0014 (13)
C40.0381 (12)0.0319 (13)0.0444 (14)0.0028 (11)0.0076 (11)0.0015 (12)
C50.0470 (12)0.0426 (15)0.0391 (13)0.0010 (12)0.0015 (11)0.0017 (12)
C60.0370 (12)0.0449 (15)0.0524 (15)0.0046 (11)0.0024 (11)0.0036 (14)
C70.0387 (12)0.0400 (15)0.0516 (15)0.0054 (11)0.0103 (11)0.0019 (13)
C80.0466 (13)0.0493 (16)0.0445 (14)0.0044 (12)0.0066 (11)0.0044 (14)
C90.0371 (11)0.0505 (16)0.0437 (13)0.0086 (12)0.0051 (11)0.0039 (13)
C100.0389 (12)0.0421 (15)0.0494 (14)0.0039 (11)0.0119 (11)0.0009 (13)
C110.0441 (12)0.0529 (16)0.0424 (14)0.0017 (13)0.0033 (11)0.0011 (13)
C120.0361 (12)0.0481 (16)0.0575 (16)0.0041 (12)0.0012 (11)0.0084 (14)
C130.0542 (15)0.076 (2)0.0522 (17)0.0137 (16)0.0037 (14)0.0022 (18)
C140.0484 (16)0.0457 (18)0.0575 (19)0.0072 (14)0.0104 (14)0.0004 (16)
N10.0439 (10)0.0508 (14)0.0530 (12)0.0016 (10)0.0014 (10)0.0085 (12)
Geometric parameters (Å, º) top
O1—C101.344 (3)C6—H60.9300
O1—H10.8200C7—C81.368 (3)
O2—C131.220 (3)C7—C121.401 (3)
N2—N11.237 (2)C8—C91.385 (3)
N2—C71.446 (3)C8—H80.9300
C1—C21.376 (3)C9—C101.411 (3)
C1—C61.393 (3)C9—C131.452 (3)
C1—N11.439 (3)C10—C111.388 (3)
C2—C31.367 (3)C11—C121.362 (3)
C2—H20.9300C11—H110.9300
C3—C41.390 (3)C12—H120.9300
C3—H30.9300C13—H131.01 (3)
C4—C51.389 (3)C14—H14C0.89 (3)
C4—C141.496 (3)C14—H14B0.94 (3)
C5—C61.378 (3)C14—H14A0.91 (3)
C5—H50.9300
C10—O1—H1109.5C7—C8—H8119.1
N1—N2—C7112.5 (2)C9—C8—H8119.1
C2—C1—C6118.8 (2)C8—C9—C10118.8 (2)
C2—C1—N1114.9 (2)C8—C9—C13120.5 (2)
C6—C1—N1126.3 (2)C10—C9—C13120.7 (2)
C3—C2—C1121.1 (2)O1—C10—C11117.7 (2)
C3—C2—H2119.4O1—C10—C9122.9 (2)
C1—C2—H2119.4C11—C10—C9119.4 (2)
C2—C3—C4121.2 (2)C12—C11—C10120.3 (2)
C2—C3—H3119.4C12—C11—H11119.9
C4—C3—H3119.4C10—C11—H11119.9
C5—C4—C3117.4 (2)C11—C12—C7121.2 (2)
C5—C4—C14121.3 (2)C11—C12—H12119.4
C3—C4—C14121.2 (2)C7—C12—H12119.4
C6—C5—C4121.6 (2)O2—C13—C9124.5 (3)
C6—C5—H5119.2O2—C13—H13120.9 (14)
C4—C5—H5119.2C9—C13—H13114.5 (14)
C5—C6—C1119.8 (2)C4—C14—H14C114 (2)
C5—C6—H6120.1C4—C14—H14B110.0 (18)
C1—C6—H6120.1H14C—C14—H14B103 (2)
C8—C7—C12118.5 (2)C4—C14—H14A114.0 (19)
C8—C7—N2116.5 (2)H14C—C14—H14A110 (3)
C12—C7—N2125.0 (2)H14B—C14—H14A106 (2)
C7—C8—C9121.9 (2)N2—N1—C1113.4 (2)
C1—N1—N2—C7179.40 (18)N2—C7—C12—C11178.9 (2)
N1—N2—C7—C124.4 (3)C8—C7—C12—C110.7 (3)
N1—N2—C7—C8176.1 (2)N2—C7—C8—C9179.5 (2)
N2—N1—C1—C63.2 (3)C12—C7—C8—C90.1 (4)
N2—N1—C1—C2177.2 (2)C7—C8—C9—C100.2 (3)
N1—C1—C6—C5179.0 (2)C7—C8—C9—C13179.4 (2)
N1—C1—C2—C3179.0 (2)C8—C9—C10—C110.0 (3)
C6—C1—C2—C30.7 (3)C8—C9—C10—O1178.9 (2)
C2—C1—C6—C50.7 (3)C8—C9—C13—O2177.2 (3)
C1—C2—C3—C40.1 (4)C10—C9—C13—O23.2 (4)
C2—C3—C4—C14179.2 (2)C13—C9—C10—O11.4 (4)
C2—C3—C4—C50.7 (3)C13—C9—C10—C11179.7 (2)
C3—C4—C5—C60.8 (3)O1—C10—C11—C12179.6 (2)
C14—C4—C5—C6179.1 (2)C9—C10—C11—C120.6 (3)
C4—C5—C6—C10.1 (3)C10—C11—C12—C70.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.962.672 (3)145
O1—H1···O2i0.822.342.863 (3)122
Symmetry code: (i) x+1, y+1, z+1.
 

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