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In the title compound, C18H20N2O3, the azobenzene unit has a trans configuration, and the two benzene rings are inclined with respect to each other by 5.9 (2)°. Mol­ecules are linked by O—H...O hydrogen bonds into a linear chain along [10\overline{1}].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029631/ci2136sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029631/ci2136Isup2.hkl
Contains datablock I

CCDC reference: 620754

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.038
  • wR factor = 0.059
  • Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low .... 28 Perc.
Author Response: The crystal is very thin (SIZE 0.07 0.293 0.37) and although the exposure time was set rather high (3 min.) the weak reflections ratio was high, so the unique data ratio above the 2 sigma level is low.

Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - C10 .. 6.35 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
1 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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) and PLUTON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(E)-2-Hydroxy-3-methoxy-5-[(4-propylphenyl)diazenyl]benzaldehyde top
Crystal data top
C18H20N2O3F(000) = 664
Mr = 312.36Dx = 1.234 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2128 reflections
a = 4.6264 (10) Åθ = 2.0–21.7°
b = 35.911 (7) ŵ = 0.09 mm1
c = 10.342 (2) ÅT = 296 K
β = 101.974 (16)°Plate, brown
V = 1680.9 (6) Å30.37 × 0.29 × 0.07 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
2983 independent reflections
Radiation source: fine-focus sealed tube831 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.079
ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
h = 55
Tmin = 0.972, Tmax = 0.989k = 4238
10696 measured reflectionsl = 1212
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.059 w = 1/[σ2(Fo2) + (0.0064P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.80(Δ/σ)max = 0.001
2983 reflectionsΔρmax = 0.11 e Å3
211 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0047 (5)
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
O20.2761 (5)0.28513 (5)0.22611 (18)0.1172 (8)
O30.6027 (5)0.25650 (6)0.08818 (15)0.0917 (7)
H30.64350.25160.15980.138*
O40.5048 (4)0.29373 (5)0.31390 (17)0.0863 (6)
N10.2078 (6)0.39437 (7)0.2334 (2)0.0816 (8)
N20.1160 (6)0.38095 (7)0.1209 (2)0.0813 (8)
C10.4025 (7)0.42586 (9)0.2311 (3)0.0778 (10)
C20.4952 (7)0.43808 (9)0.1202 (3)0.0912 (11)
H20.43740.42550.04050.109*
C30.6743 (8)0.46912 (10)0.1277 (3)0.0950 (11)
H3A0.73570.47710.05220.114*
C40.7642 (7)0.48849 (9)0.2438 (4)0.0812 (9)
C50.6755 (7)0.47544 (10)0.3545 (3)0.0997 (11)
H50.73670.48760.43490.120*
C60.4960 (7)0.44440 (9)0.3472 (3)0.0917 (10)
H60.43800.43600.42310.110*
C70.0753 (7)0.34951 (9)0.1220 (3)0.0742 (10)
C80.1408 (7)0.33025 (9)0.0050 (3)0.0793 (10)
H80.06610.33840.06680.095*
C90.3181 (7)0.29861 (9)0.0073 (3)0.0725 (9)
C100.4297 (7)0.28735 (8)0.1003 (3)0.0725 (9)
C110.3715 (7)0.30797 (8)0.2196 (3)0.0712 (9)
C120.1926 (7)0.33848 (8)0.2292 (3)0.0722 (9)
H120.14910.35190.30760.087*
C130.3782 (7)0.27722 (8)0.1300 (3)0.1013 (12)
H130.50070.25650.13520.122*
C140.4644 (6)0.31384 (7)0.4360 (2)0.0983 (10)
H14A0.25750.31520.47520.148*
H14B0.56640.30130.49520.148*
H14C0.54230.33860.41940.148*
C150.9490 (7)0.52351 (9)0.2484 (3)0.0979 (10)
H15A1.01010.52630.16470.117*
H15B1.12600.52080.31690.117*
C160.7869 (7)0.55867 (9)0.2754 (3)0.0956 (9)
H16A0.60750.56100.20800.115*
H16B0.72960.55600.35990.115*
C170.9640 (7)0.59412 (9)0.2775 (3)0.1098 (11)
H17A1.14570.59160.34330.132*
H17B1.01740.59710.19220.132*
C180.8085 (8)0.62852 (8)0.3069 (3)0.1509 (15)
H18A0.93740.64960.30910.226*
H18B0.75400.62590.39110.226*
H18C0.63420.63220.23940.226*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.201 (2)0.0790 (16)0.0887 (14)0.0078 (16)0.0695 (16)0.0048 (13)
O30.134 (2)0.0796 (16)0.0695 (13)0.0125 (14)0.0384 (14)0.0033 (12)
O40.1156 (18)0.0827 (15)0.0667 (12)0.0047 (12)0.0330 (12)0.0019 (12)
N10.084 (2)0.069 (2)0.0896 (19)0.0043 (16)0.0138 (17)0.0052 (16)
N20.092 (2)0.069 (2)0.0833 (19)0.0093 (16)0.0186 (17)0.0017 (15)
C10.085 (3)0.070 (3)0.079 (2)0.0075 (19)0.018 (2)0.007 (2)
C20.105 (3)0.081 (3)0.091 (3)0.003 (2)0.027 (2)0.002 (2)
C30.105 (3)0.091 (3)0.094 (3)0.003 (2)0.032 (2)0.008 (2)
C40.069 (2)0.076 (3)0.101 (3)0.002 (2)0.021 (2)0.005 (2)
C50.107 (3)0.105 (3)0.088 (3)0.024 (2)0.022 (2)0.003 (2)
C60.100 (3)0.098 (3)0.080 (2)0.011 (2)0.028 (2)0.002 (2)
C70.081 (3)0.061 (2)0.083 (2)0.0064 (19)0.021 (2)0.003 (2)
C80.099 (3)0.068 (2)0.077 (2)0.011 (2)0.035 (2)0.0105 (18)
C90.096 (3)0.060 (2)0.067 (2)0.004 (2)0.030 (2)0.0033 (19)
C100.085 (3)0.057 (2)0.080 (2)0.0020 (19)0.025 (2)0.0037 (19)
C110.088 (3)0.062 (2)0.066 (2)0.0082 (19)0.022 (2)0.0039 (19)
C120.089 (3)0.068 (2)0.0626 (19)0.0130 (19)0.0219 (18)0.0016 (18)
C130.154 (3)0.079 (3)0.079 (2)0.007 (2)0.044 (2)0.004 (2)
C140.140 (3)0.095 (2)0.0650 (18)0.008 (2)0.0327 (19)0.0071 (18)
C150.084 (3)0.090 (3)0.121 (3)0.005 (2)0.025 (2)0.010 (2)
C160.101 (3)0.086 (2)0.106 (2)0.008 (2)0.035 (2)0.004 (2)
C170.112 (3)0.093 (2)0.130 (3)0.023 (3)0.040 (2)0.001 (2)
C180.173 (4)0.094 (3)0.209 (4)0.015 (3)0.091 (3)0.037 (3)
Geometric parameters (Å, º) top
O2—C131.219 (2)C8—H80.93
O3—C101.357 (3)C9—C101.381 (3)
O3—H30.82C9—C131.460 (3)
O4—C111.357 (3)C10—C111.416 (3)
O4—C141.433 (2)C11—C121.364 (3)
N1—N21.250 (2)C12—H120.93
N1—C11.449 (3)C13—H130.93
N2—C71.436 (3)C14—H14A0.96
C1—C61.363 (3)C14—H14B0.96
C1—C21.377 (3)C14—H14C0.96
C2—C31.381 (3)C15—C161.523 (3)
C2—H20.93C15—H15A0.97
C3—C41.375 (3)C15—H15B0.97
C3—H3A0.93C16—C171.512 (3)
C4—C51.376 (3)C16—H16A0.97
C4—C151.516 (4)C16—H16B0.97
C5—C61.383 (3)C17—C181.492 (3)
C5—H50.93C17—H17A0.97
C6—H60.93C17—H17B0.97
C7—C81.372 (3)C18—H18A0.96
C7—C121.389 (3)C18—H18B0.96
C8—C91.392 (3)C18—H18C0.96
C10—O3—H3109.5C11—C12—C7120.2 (3)
C11—O4—C14116.6 (2)C11—C12—H12119.9
N2—N1—C1112.2 (3)C7—C12—H12119.9
N1—N2—C7112.8 (3)O2—C13—C9123.3 (3)
C6—C1—C2118.8 (3)O2—C13—H13118.3
C6—C1—N1116.8 (3)C9—C13—H13118.3
C2—C1—N1124.4 (3)O4—C14—H14A109.5
C1—C2—C3119.9 (3)O4—C14—H14B109.5
C1—C2—H2120.1H14A—C14—H14B109.5
C3—C2—H2120.1O4—C14—H14C109.5
C4—C3—C2121.7 (3)H14A—C14—H14C109.5
C4—C3—H3A119.1H14B—C14—H14C109.5
C2—C3—H3A119.1C4—C15—C16113.4 (3)
C3—C4—C5117.8 (3)C4—C15—H15A108.9
C3—C4—C15120.9 (3)C16—C15—H15A108.9
C5—C4—C15121.3 (3)C4—C15—H15B108.9
C4—C5—C6120.6 (3)C16—C15—H15B108.9
C4—C5—H5119.7H15A—C15—H15B107.7
C6—C5—H5119.7C17—C16—C15114.5 (3)
C1—C6—C5121.2 (3)C17—C16—H16A108.6
C1—C6—H6119.4C15—C16—H16A108.6
C5—C6—H6119.4C17—C16—H16B108.6
C8—C7—C12120.6 (3)C15—C16—H16B108.6
C8—C7—N2114.4 (3)H16A—C16—H16B107.6
C12—C7—N2125.0 (3)C18—C17—C16114.7 (3)
C7—C8—C9120.7 (3)C18—C17—H17A108.6
C7—C8—H8119.7C16—C17—H17A108.6
C9—C8—H8119.7C18—C17—H17B108.6
C10—C9—C8118.5 (3)C16—C17—H17B108.6
C10—C9—C13120.7 (3)H17A—C17—H17B107.6
C8—C9—C13120.8 (3)C17—C18—H18A109.5
O3—C10—C9118.5 (3)C17—C18—H18B109.5
O3—C10—C11120.6 (3)H18A—C18—H18B109.5
C9—C10—C11120.9 (3)C17—C18—H18C109.5
O4—C11—C12127.6 (3)H18A—C18—H18C109.5
O4—C11—C10113.3 (3)H18B—C18—H18C109.5
C12—C11—C10119.1 (3)
C1—N1—N2—C7179.5 (2)C13—C9—C10—O31.7 (4)
N2—N1—C1—C6174.9 (3)C8—C9—C10—C111.5 (4)
N2—N1—C1—C24.6 (4)C13—C9—C10—C11179.9 (3)
C6—C1—C2—C31.4 (5)C14—O4—C11—C123.0 (4)
N1—C1—C2—C3178.1 (3)C14—O4—C11—C10177.9 (2)
C1—C2—C3—C40.0 (5)O3—C10—C11—O40.3 (4)
C2—C3—C4—C51.5 (5)C9—C10—C11—O4178.1 (2)
C2—C3—C4—C15177.1 (3)O3—C10—C11—C12178.9 (3)
C3—C4—C5—C61.5 (5)C9—C10—C11—C122.7 (4)
C15—C4—C5—C6177.1 (3)O4—C11—C12—C7179.5 (3)
C2—C1—C6—C51.4 (5)C10—C11—C12—C71.5 (4)
N1—C1—C6—C5178.1 (3)C8—C7—C12—C110.9 (4)
C4—C5—C6—C10.1 (5)N2—C7—C12—C11179.7 (3)
N1—N2—C7—C8169.7 (3)C10—C9—C13—O2177.2 (3)
N1—N2—C7—C1210.9 (4)C8—C9—C13—O21.2 (5)
C12—C7—C8—C92.1 (4)C3—C4—C15—C16112.7 (3)
N2—C7—C8—C9178.4 (3)C5—C4—C15—C1665.9 (4)
C7—C8—C9—C100.9 (4)C4—C15—C16—C17178.7 (3)
C7—C8—C9—C13177.5 (3)C15—C16—C17—C18178.7 (3)
C8—C9—C10—O3179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.822.192.646 (2)115
O3—H3···O2i0.821.952.685 (2)148
Symmetry code: (i) x1/2, y+1/2, z+1/2.
 

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