(E)-2-Hydr­oxy-3-meth­oxy-5-[(4-propyl­phen­yl)diazenyl]benzaldehyde

Karadayı, N.; Albayrak, Ç.; Odabaşoğlu, M.; Büyükgüngör, O.

doi:10.1107/S1600536806029631

(E)-2-Hydroxy-3-methoxy-5-[(4-propylphenyl)diazenyl]benzaldehyde

N. Karadayı, Ç. Albayrak, M. Odabaşoğlu and O. Büyükgüngör

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 $\overline{1}$ ].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029631/ci2136sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029631/ci2136Isup2.hkl Contains datablock I

CCDC reference: 620754

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (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

C₁₈H₂₀N₂O₃	F(000) = 664
M_r = 312.36	D_x = 1.234 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2128 reflections
a = 4.6264 (10) Å	θ = 2.0–21.7°
b = 35.911 (7) Å	µ = 0.09 mm⁻¹
c = 10.342 (2) Å	T = 296 K
β = 101.974 (16)°	Plate, brown
V = 1680.9 (6) Å³	0.37 × 0.29 × 0.07 mm
Z = 4

Data collection top

Stoe IPDS-2 diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	831 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.079
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −5→5
T_min = 0.972, T_max = 0.989	k = −42→38
10696 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.0064P)²] where P = (F_o² + 2F_c²)/3
S = 0.80	(Δ/σ)_max = 0.001
2983 reflections	Δρ_max = 0.11 e Å⁻³
211 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction 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

	x	y	z	U_iso*/U_eq
O2	−0.2761 (5)	0.28513 (5)	−0.22611 (18)	0.1172 (8)
O3	−0.6027 (5)	0.25650 (6)	0.08818 (15)	0.0917 (7)
H3	−0.6435	0.2516	0.1598	0.138*
O4	−0.5048 (4)	0.29373 (5)	0.31390 (17)	0.0863 (6)
N1	0.2078 (6)	0.39437 (7)	0.2334 (2)	0.0816 (8)
N2	0.1160 (6)	0.38095 (7)	0.1209 (2)	0.0813 (8)
C1	0.4025 (7)	0.42586 (9)	0.2311 (3)	0.0778 (10)
C2	0.4952 (7)	0.43808 (9)	0.1202 (3)	0.0912 (11)
H2	0.4374	0.4255	0.0405	0.109*
C3	0.6743 (8)	0.46912 (10)	0.1277 (3)	0.0950 (11)
H3A	0.7357	0.4771	0.0522	0.114*
C4	0.7642 (7)	0.48849 (9)	0.2438 (4)	0.0812 (9)
C5	0.6755 (7)	0.47544 (10)	0.3545 (3)	0.0997 (11)
H5	0.7367	0.4876	0.4349	0.120*
C6	0.4960 (7)	0.44440 (9)	0.3472 (3)	0.0917 (10)
H6	0.4380	0.4360	0.4231	0.110*
C7	−0.0753 (7)	0.34951 (9)	0.1220 (3)	0.0742 (10)
C8	−0.1408 (7)	0.33025 (9)	0.0050 (3)	0.0793 (10)
H8	−0.0661	0.3384	−0.0668	0.095*
C9	−0.3181 (7)	0.29861 (9)	−0.0073 (3)	0.0725 (9)
C10	−0.4297 (7)	0.28735 (8)	0.1003 (3)	0.0725 (9)
C11	−0.3715 (7)	0.30797 (8)	0.2196 (3)	0.0712 (9)
C12	−0.1926 (7)	0.33848 (8)	0.2292 (3)	0.0722 (9)
H12	−0.1491	0.3519	0.3076	0.087*
C13	−0.3782 (7)	0.27722 (8)	−0.1300 (3)	0.1013 (12)
H13	−0.5007	0.2565	−0.1352	0.122*
C14	−0.4644 (6)	0.31384 (7)	0.4360 (2)	0.0983 (10)
H14A	−0.2575	0.3152	0.4752	0.148*
H14B	−0.5664	0.3013	0.4952	0.148*
H14C	−0.5423	0.3386	0.4194	0.148*
C15	0.9490 (7)	0.52351 (9)	0.2484 (3)	0.0979 (10)
H15A	1.0101	0.5263	0.1647	0.117*
H15B	1.1260	0.5208	0.3169	0.117*
C16	0.7869 (7)	0.55867 (9)	0.2754 (3)	0.0956 (9)
H16A	0.6075	0.5610	0.2080	0.115*
H16B	0.7296	0.5560	0.3599	0.115*
C17	0.9640 (7)	0.59412 (9)	0.2775 (3)	0.1098 (11)
H17A	1.1457	0.5916	0.3433	0.132*
H17B	1.0174	0.5971	0.1922	0.132*
C18	0.8085 (8)	0.62852 (8)	0.3069 (3)	0.1509 (15)
H18A	0.9374	0.6496	0.3091	0.226*
H18B	0.7540	0.6259	0.3911	0.226*
H18C	0.6342	0.6322	0.2394	0.226*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.201 (2)	0.0790 (16)	0.0887 (14)	−0.0078 (16)	0.0695 (16)	−0.0048 (13)
O3	0.134 (2)	0.0796 (16)	0.0695 (13)	−0.0125 (14)	0.0384 (14)	−0.0033 (12)
O4	0.1156 (18)	0.0827 (15)	0.0667 (12)	−0.0047 (12)	0.0330 (12)	−0.0019 (12)
N1	0.084 (2)	0.069 (2)	0.0896 (19)	0.0043 (16)	0.0138 (17)	0.0052 (16)
N2	0.092 (2)	0.069 (2)	0.0833 (19)	0.0093 (16)	0.0186 (17)	0.0017 (15)
C1	0.085 (3)	0.070 (3)	0.079 (2)	0.0075 (19)	0.018 (2)	0.007 (2)
C2	0.105 (3)	0.081 (3)	0.091 (3)	−0.003 (2)	0.027 (2)	0.002 (2)
C3	0.105 (3)	0.091 (3)	0.094 (3)	0.003 (2)	0.032 (2)	0.008 (2)
C4	0.069 (2)	0.076 (3)	0.101 (3)	0.002 (2)	0.021 (2)	0.005 (2)
C5	0.107 (3)	0.105 (3)	0.088 (3)	−0.024 (2)	0.022 (2)	−0.003 (2)
C6	0.100 (3)	0.098 (3)	0.080 (2)	−0.011 (2)	0.028 (2)	0.002 (2)
C7	0.081 (3)	0.061 (2)	0.083 (2)	0.0064 (19)	0.021 (2)	0.003 (2)
C8	0.099 (3)	0.068 (2)	0.077 (2)	0.011 (2)	0.035 (2)	0.0105 (18)
C9	0.096 (3)	0.060 (2)	0.067 (2)	0.004 (2)	0.030 (2)	0.0033 (19)
C10	0.085 (3)	0.057 (2)	0.080 (2)	0.0020 (19)	0.025 (2)	0.0037 (19)
C11	0.088 (3)	0.062 (2)	0.066 (2)	0.0082 (19)	0.022 (2)	0.0039 (19)
C12	0.089 (3)	0.068 (2)	0.0626 (19)	0.0130 (19)	0.0219 (18)	0.0016 (18)
C13	0.154 (3)	0.079 (3)	0.079 (2)	−0.007 (2)	0.044 (2)	−0.004 (2)
C14	0.140 (3)	0.095 (2)	0.0650 (18)	0.008 (2)	0.0327 (19)	−0.0071 (18)
C15	0.084 (3)	0.090 (3)	0.121 (3)	−0.005 (2)	0.025 (2)	0.010 (2)
C16	0.101 (3)	0.086 (2)	0.106 (2)	−0.008 (2)	0.035 (2)	−0.004 (2)
C17	0.112 (3)	0.093 (2)	0.130 (3)	−0.023 (3)	0.040 (2)	−0.001 (2)
C18	0.173 (4)	0.094 (3)	0.209 (4)	−0.015 (3)	0.091 (3)	−0.037 (3)

Geometric parameters (Å, º) top

O2—C13	1.219 (2)	C8—H8	0.93
O3—C10	1.357 (3)	C9—C10	1.381 (3)
O3—H3	0.82	C9—C13	1.460 (3)
O4—C11	1.357 (3)	C10—C11	1.416 (3)
O4—C14	1.433 (2)	C11—C12	1.364 (3)
N1—N2	1.250 (2)	C12—H12	0.93
N1—C1	1.449 (3)	C13—H13	0.93
N2—C7	1.436 (3)	C14—H14A	0.96
C1—C6	1.363 (3)	C14—H14B	0.96
C1—C2	1.377 (3)	C14—H14C	0.96
C2—C3	1.381 (3)	C15—C16	1.523 (3)
C2—H2	0.93	C15—H15A	0.97
C3—C4	1.375 (3)	C15—H15B	0.97
C3—H3A	0.93	C16—C17	1.512 (3)
C4—C5	1.376 (3)	C16—H16A	0.97
C4—C15	1.516 (4)	C16—H16B	0.97
C5—C6	1.383 (3)	C17—C18	1.492 (3)
C5—H5	0.93	C17—H17A	0.97
C6—H6	0.93	C17—H17B	0.97
C7—C8	1.372 (3)	C18—H18A	0.96
C7—C12	1.389 (3)	C18—H18B	0.96
C8—C9	1.392 (3)	C18—H18C	0.96

C10—O3—H3	109.5	C11—C12—C7	120.2 (3)
C11—O4—C14	116.6 (2)	C11—C12—H12	119.9
N2—N1—C1	112.2 (3)	C7—C12—H12	119.9
N1—N2—C7	112.8 (3)	O2—C13—C9	123.3 (3)
C6—C1—C2	118.8 (3)	O2—C13—H13	118.3
C6—C1—N1	116.8 (3)	C9—C13—H13	118.3
C2—C1—N1	124.4 (3)	O4—C14—H14A	109.5
C1—C2—C3	119.9 (3)	O4—C14—H14B	109.5
C1—C2—H2	120.1	H14A—C14—H14B	109.5
C3—C2—H2	120.1	O4—C14—H14C	109.5
C4—C3—C2	121.7 (3)	H14A—C14—H14C	109.5
C4—C3—H3A	119.1	H14B—C14—H14C	109.5
C2—C3—H3A	119.1	C4—C15—C16	113.4 (3)
C3—C4—C5	117.8 (3)	C4—C15—H15A	108.9
C3—C4—C15	120.9 (3)	C16—C15—H15A	108.9
C5—C4—C15	121.3 (3)	C4—C15—H15B	108.9
C4—C5—C6	120.6 (3)	C16—C15—H15B	108.9
C4—C5—H5	119.7	H15A—C15—H15B	107.7
C6—C5—H5	119.7	C17—C16—C15	114.5 (3)
C1—C6—C5	121.2 (3)	C17—C16—H16A	108.6
C1—C6—H6	119.4	C15—C16—H16A	108.6
C5—C6—H6	119.4	C17—C16—H16B	108.6
C8—C7—C12	120.6 (3)	C15—C16—H16B	108.6
C8—C7—N2	114.4 (3)	H16A—C16—H16B	107.6
C12—C7—N2	125.0 (3)	C18—C17—C16	114.7 (3)
C7—C8—C9	120.7 (3)	C18—C17—H17A	108.6
C7—C8—H8	119.7	C16—C17—H17A	108.6
C9—C8—H8	119.7	C18—C17—H17B	108.6
C10—C9—C8	118.5 (3)	C16—C17—H17B	108.6
C10—C9—C13	120.7 (3)	H17A—C17—H17B	107.6
C8—C9—C13	120.8 (3)	C17—C18—H18A	109.5
O3—C10—C9	118.5 (3)	C17—C18—H18B	109.5
O3—C10—C11	120.6 (3)	H18A—C18—H18B	109.5
C9—C10—C11	120.9 (3)	C17—C18—H18C	109.5
O4—C11—C12	127.6 (3)	H18A—C18—H18C	109.5
O4—C11—C10	113.3 (3)	H18B—C18—H18C	109.5
C12—C11—C10	119.1 (3)

C1—N1—N2—C7	179.5 (2)	C13—C9—C10—O3	−1.7 (4)
N2—N1—C1—C6	174.9 (3)	C8—C9—C10—C11	1.5 (4)
N2—N1—C1—C2	−4.6 (4)	C13—C9—C10—C11	179.9 (3)
C6—C1—C2—C3	−1.4 (5)	C14—O4—C11—C12	3.0 (4)
N1—C1—C2—C3	178.1 (3)	C14—O4—C11—C10	−177.9 (2)
C1—C2—C3—C4	0.0 (5)	O3—C10—C11—O4	−0.3 (4)
C2—C3—C4—C5	1.5 (5)	C9—C10—C11—O4	178.1 (2)
C2—C3—C4—C15	−177.1 (3)	O3—C10—C11—C12	178.9 (3)
C3—C4—C5—C6	−1.5 (5)	C9—C10—C11—C12	−2.7 (4)
C15—C4—C5—C6	177.1 (3)	O4—C11—C12—C7	−179.5 (3)
C2—C1—C6—C5	1.4 (5)	C10—C11—C12—C7	1.5 (4)
N1—C1—C6—C5	−178.1 (3)	C8—C7—C12—C11	0.9 (4)
C4—C5—C6—C1	0.1 (5)	N2—C7—C12—C11	−179.7 (3)
N1—N2—C7—C8	−169.7 (3)	C10—C9—C13—O2	−177.2 (3)
N1—N2—C7—C12	10.9 (4)	C8—C9—C13—O2	1.2 (5)
C12—C7—C8—C9	−2.1 (4)	C3—C4—C15—C16	112.7 (3)
N2—C7—C8—C9	178.4 (3)	C5—C4—C15—C16	−65.9 (4)
C7—C8—C9—C10	0.9 (4)	C4—C15—C16—C17	−178.7 (3)
C7—C8—C9—C13	−177.5 (3)	C15—C16—C17—C18	−178.7 (3)
C8—C9—C10—O3	179.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	2.19	2.646 (2)	115
O3—H3···O2ⁱ	0.82	1.95	2.685 (2)	148

Symmetry code: (i) x−1/2, −y+1/2, z+1/2.

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(E)-2-Hydr­oxy-3-meth­oxy-5-[(4-propyl­phen­yl)diazenyl]benzaldehyde

Supporting information

Key indicators

checkCIF/PLATON results

(E)-2-Hydroxy-3-methoxy-5-[(4-propylphenyl)diazenyl]benzaldehyde