In the title compound, C
16H
16N
2O·H
2O, the azobenzene moiety has a
trans configuration, and the two phenyl rings are inclined with respect to each other by 14.23 (17)°. There are intermolecular O—H
O and O—H
N hydrogen bonds involving the water molecule.
Supporting information
CCDC reference: 234857
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.068
- wR factor = 0.180
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level B
RINTA01_ALERT_3_B The value of Rint is greater than 0.15
Rint given 0.175
PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.17
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 31 Perc.
PLAT241_ALERT_2_B Check High U(eq) as Compared to Neighbors .... C16
PLAT731_ALERT_1_B Bond Calc 0.88(11), Rep 0.87(2) ...... 5.50 su-Rat
O2 -H1A 1.555 1.555
PLAT735_ALERT_1_B D-H Calc 0.88(11), Rep 0.87(2) ...... 5.50 su-Rat
O2 -H1A 1.555 1.555
Alert level C
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C15A
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C15B
PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
0 ALERT level A = In general: serious problem
6 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
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
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: ORTEPIII (Burnett & Johnson, 1996); PLUTON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
p-[p
'-methylphenylazo]-
o-allylphenol monohydrate
top
Crystal data top
C16H16N2O·H2O | F(000) = 1152 |
Mr = 270.32 | Dx = 1.205 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 3655 reflections |
a = 27.2961 (9) Å | θ = 1.5–21.6° |
b = 14.4293 (17) Å | µ = 0.08 mm−1 |
c = 7.568 (4) Å | T = 293 K |
V = 2980.8 (16) Å3 | Prism, light brown |
Z = 8 | 0.30 × 0.17 × 0.10 mm |
Data collection top
STOE IPDS 2 diffractometer | 806 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.175 |
Plane graphite monochromator | θmax = 25.0°, θmin = 1.5° |
ω? scans | h = −32→32 |
17874 measured reflections | k = −17→17 |
2629 independent reflections | l = −8→8 |
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)] = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.180 | w = 1/[σ2(Fo2) + (0.062P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.88 | (Δ/σ)max = 0.030 |
2629 reflections | Δρmax = 0.22 e Å−3 |
202 parameters | Δρmin = −0.19 e Å−3 |
29 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0040 (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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C15A | 0.4384 (3) | 0.3755 (6) | 0.4272 (17) | 0.0800 (17) | 0.677 (10) |
H15A | 0.4437 | 0.3944 | 0.3112 | 0.096* | 0.677 (10) |
C15B | 0.4303 (6) | 0.3852 (13) | 0.559 (3) | 0.0799 (17) | 0.323 (10) |
H15B | 0.4239 | 0.4169 | 0.6640 | 0.096* | 0.323 (10) |
O1 | 0.29396 (16) | 0.3165 (2) | 0.3329 (6) | 0.0769 (13) | |
H1 | 0.2746 | 0.3106 | 0.2509 | 0.115* | |
O2 | 0.21137 (17) | 0.2925 (3) | 0.1485 (7) | 0.0819 (14) | |
N1 | 0.33785 (17) | 0.6899 (3) | 0.4275 (6) | 0.0610 (13) | |
N2 | 0.37711 (18) | 0.7089 (3) | 0.5103 (6) | 0.0664 (14) | |
C1 | 0.3051 (2) | 0.4089 (4) | 0.3547 (7) | 0.0581 (16) | |
C2 | 0.3514 (2) | 0.4296 (4) | 0.4216 (7) | 0.0575 (15) | |
C3 | 0.3630 (2) | 0.5233 (4) | 0.4480 (8) | 0.0623 (16) | |
H3 | 0.3934 | 0.5398 | 0.4938 | 0.075* | |
C4 | 0.3285 (2) | 0.5923 (4) | 0.4048 (7) | 0.0578 (16) | |
C5 | 0.2850 (2) | 0.5685 (4) | 0.3334 (8) | 0.0694 (17) | |
H5 | 0.2631 | 0.6148 | 0.3006 | 0.083* | |
C6 | 0.2722 (2) | 0.4767 (4) | 0.3080 (8) | 0.0656 (17) | |
H6 | 0.2419 | 0.4611 | 0.2602 | 0.079* | |
C7 | 0.3835 (2) | 0.8079 (4) | 0.5334 (7) | 0.0596 (16) | |
C8 | 0.4308 (3) | 0.8356 (4) | 0.5647 (8) | 0.0723 (18) | |
H8 | 0.4557 | 0.7920 | 0.5755 | 0.087* | |
C9 | 0.4409 (2) | 0.9290 (4) | 0.5799 (8) | 0.0739 (18) | |
H9 | 0.4730 | 0.9479 | 0.5992 | 0.089* | |
C10 | 0.4043 (3) | 0.9954 (4) | 0.5672 (8) | 0.0654 (17) | |
C11 | 0.3575 (3) | 0.9637 (4) | 0.5412 (8) | 0.0743 (19) | |
H11 | 0.3322 | 1.0068 | 0.5360 | 0.089* | |
C12 | 0.3462 (2) | 0.8717 (4) | 0.5227 (8) | 0.0683 (18) | |
H12 | 0.3141 | 0.8529 | 0.5032 | 0.082* | |
C13 | 0.4161 (2) | 1.0971 (4) | 0.5803 (8) | 0.087 (2) | |
H13A | 0.4049 | 1.1206 | 0.6919 | 0.130* | |
H13B | 0.4000 | 1.1299 | 0.4862 | 0.130* | |
H13C | 0.4509 | 1.1058 | 0.5710 | 0.130* | |
C14 | 0.3876 (2) | 0.3526 (4) | 0.4624 (9) | 0.0797 (16) | |
H14A | 0.3845 | 0.3361 | 0.5861 | 0.096* | |
H14B | 0.3789 | 0.2985 | 0.3932 | 0.096* | |
C16 | 0.4765 (3) | 0.3755 (6) | 0.5178 (14) | 0.168 (4) | |
H16A | 0.4753 | 0.3578 | 0.6359 | 0.202* | |
H16B | 0.5061 | 0.3933 | 0.4674 | 0.202* | |
H1A | 0.200 (6) | 0.240 (6) | 0.19 (2) | 0.38 (9)* | |
H1B | 0.211 (5) | 0.288 (9) | 0.037 (3) | 0.29 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C15A | 0.080 (3) | 0.058 (3) | 0.102 (4) | 0.003 (3) | 0.000 (3) | 0.000 (3) |
C15B | 0.080 (3) | 0.058 (3) | 0.102 (4) | 0.003 (3) | −0.001 (3) | 0.000 (3) |
O1 | 0.098 (4) | 0.055 (3) | 0.078 (3) | −0.011 (2) | −0.008 (2) | −0.005 (2) |
O2 | 0.091 (3) | 0.074 (3) | 0.081 (3) | −0.017 (3) | −0.004 (3) | −0.009 (3) |
N1 | 0.075 (4) | 0.055 (3) | 0.053 (3) | −0.004 (3) | −0.002 (3) | 0.003 (3) |
N2 | 0.075 (4) | 0.059 (3) | 0.066 (3) | −0.007 (3) | −0.002 (3) | 0.003 (3) |
C1 | 0.071 (5) | 0.051 (4) | 0.052 (4) | 0.000 (3) | 0.006 (3) | 0.007 (3) |
C2 | 0.058 (4) | 0.057 (4) | 0.058 (4) | −0.003 (3) | 0.001 (3) | 0.001 (3) |
C3 | 0.068 (4) | 0.058 (4) | 0.061 (4) | −0.001 (3) | 0.006 (3) | 0.001 (3) |
C4 | 0.073 (5) | 0.051 (4) | 0.049 (4) | −0.003 (3) | −0.001 (3) | 0.000 (3) |
C5 | 0.074 (5) | 0.062 (4) | 0.072 (4) | 0.001 (4) | −0.008 (4) | 0.005 (4) |
C6 | 0.054 (4) | 0.067 (4) | 0.076 (4) | −0.009 (3) | −0.008 (3) | 0.005 (4) |
C7 | 0.068 (4) | 0.056 (4) | 0.055 (4) | −0.005 (4) | 0.006 (3) | 0.003 (3) |
C8 | 0.088 (5) | 0.062 (4) | 0.067 (4) | 0.000 (4) | −0.003 (4) | −0.002 (4) |
C9 | 0.072 (5) | 0.073 (5) | 0.077 (5) | −0.015 (4) | −0.010 (4) | 0.005 (4) |
C10 | 0.084 (5) | 0.060 (4) | 0.052 (4) | −0.003 (4) | 0.005 (4) | −0.007 (3) |
C11 | 0.086 (5) | 0.072 (5) | 0.065 (5) | 0.008 (4) | 0.003 (4) | −0.013 (4) |
C12 | 0.074 (5) | 0.055 (4) | 0.075 (5) | 0.004 (4) | −0.001 (3) | −0.011 (4) |
C13 | 0.122 (6) | 0.061 (4) | 0.077 (5) | −0.011 (4) | 0.017 (4) | −0.004 (4) |
C14 | 0.080 (3) | 0.058 (3) | 0.102 (4) | 0.003 (3) | −0.001 (3) | 0.000 (3) |
C16 | 0.171 (4) | 0.087 (9) | 0.132 (12) | 0.007 (6) | −0.031 (5) | −0.011 (9) |
Geometric parameters (Å, º) top
C15A—C16 | 1.247 (10) | C5—H5 | 0.9300 |
C15A—C14 | 1.449 (9) | C6—H6 | 0.9300 |
C15A—H15A | 0.9300 | C7—C8 | 1.372 (7) |
C15B—C16 | 1.309 (15) | C7—C12 | 1.374 (7) |
C15B—C14 | 1.454 (15) | C8—C9 | 1.381 (7) |
C15B—H15B | 0.9300 | C8—H8 | 0.9300 |
O1—C1 | 1.378 (6) | C9—C10 | 1.387 (7) |
O1—H1 | 0.8200 | C9—H9 | 0.9300 |
O2—H1A | 0.87 (2) | C10—C11 | 1.370 (7) |
O2—H1B | 0.84 (2) | C10—C13 | 1.506 (7) |
N1—N2 | 1.272 (5) | C11—C12 | 1.370 (7) |
N1—C4 | 1.441 (6) | C11—H11 | 0.9300 |
N2—C7 | 1.450 (6) | C12—H12 | 0.9300 |
C1—C6 | 1.374 (7) | C13—H13A | 0.9600 |
C1—C2 | 1.392 (7) | C13—H13B | 0.9600 |
C2—C3 | 1.403 (7) | C13—H13C | 0.9600 |
C2—C14 | 1.520 (7) | C14—H14A | 0.9700 |
C3—C4 | 1.410 (7) | C14—H14B | 0.9700 |
C3—H3 | 0.9300 | C16—H16A | 0.9300 |
C4—C5 | 1.348 (7) | C16—H16B | 0.9300 |
C5—C6 | 1.383 (7) | | |
| | | |
C16—C15A—C14 | 134.2 (11) | C7—C8—C9 | 119.1 (6) |
C16—C15A—H15A | 112.9 | C7—C8—H8 | 120.5 |
C14—C15A—H15A | 112.9 | C9—C8—H8 | 120.5 |
C16—C15B—C14 | 128.0 (18) | C8—C9—C10 | 121.7 (6) |
C16—C15B—H15B | 116.0 | C8—C9—H9 | 119.2 |
C14—C15B—H15B | 116.0 | C10—C9—H9 | 119.2 |
C1—O1—H1 | 109.5 | C11—C10—C9 | 116.8 (6) |
H1A—O2—H1B | 105 (10) | C11—C10—C13 | 122.3 (6) |
N2—N1—C4 | 114.8 (5) | C9—C10—C13 | 121.0 (6) |
N1—N2—C7 | 111.9 (5) | C12—C11—C10 | 123.2 (6) |
C6—C1—O1 | 120.9 (6) | C12—C11—H11 | 118.4 |
C6—C1—C2 | 122.2 (5) | C10—C11—H11 | 118.4 |
O1—C1—C2 | 116.9 (5) | C11—C12—C7 | 118.4 (6) |
C1—C2—C3 | 117.7 (5) | C11—C12—H12 | 120.8 |
C1—C2—C14 | 120.5 (5) | C7—C12—H12 | 120.8 |
C3—C2—C14 | 121.8 (5) | C10—C13—H13A | 109.5 |
C2—C3—C4 | 119.7 (5) | C10—C13—H13B | 109.5 |
C2—C3—H3 | 120.2 | H13A—C13—H13B | 109.5 |
C4—C3—H3 | 120.2 | C10—C13—H13C | 109.5 |
C5—C4—C3 | 120.1 (5) | H13A—C13—H13C | 109.5 |
C5—C4—N1 | 117.0 (5) | H13B—C13—H13C | 109.5 |
C3—C4—N1 | 122.9 (5) | C15A—C14—C2 | 114.7 (6) |
C4—C5—C6 | 121.5 (6) | C15B—C14—C2 | 112.8 (9) |
C4—C5—H5 | 119.3 | C15A—C14—H14A | 108.6 |
C6—C5—H5 | 119.3 | C2—C14—H14A | 108.6 |
C1—C6—C5 | 118.7 (5) | C15A—C14—H14B | 108.6 |
C1—C6—H6 | 120.6 | C2—C14—H14B | 108.6 |
C5—C6—H6 | 120.6 | H14A—C14—H14B | 107.6 |
C8—C7—C12 | 120.8 (6) | C15A—C16—H16A | 120.0 |
C8—C7—N2 | 114.8 (6) | C15A—C16—H16B | 120.0 |
C12—C7—N2 | 124.4 (6) | H16A—C16—H16B | 120.0 |
| | | |
C4—N1—N2—C7 | −178.1 (5) | N2—C7—C8—C9 | 176.9 (5) |
C6—C1—C2—C3 | 2.7 (8) | C7—C8—C9—C10 | 1.0 (10) |
O1—C1—C2—C3 | −178.7 (5) | C8—C9—C10—C11 | 0.9 (10) |
C6—C1—C2—C14 | −176.7 (6) | C8—C9—C10—C13 | −178.7 (6) |
O1—C1—C2—C14 | 1.8 (8) | C9—C10—C11—C12 | −2.0 (10) |
C1—C2—C3—C4 | −0.7 (8) | C13—C10—C11—C12 | 177.6 (6) |
C14—C2—C3—C4 | 178.7 (5) | C10—C11—C12—C7 | 1.1 (10) |
C2—C3—C4—C5 | −2.0 (8) | C8—C7—C12—C11 | 1.0 (9) |
C2—C3—C4—N1 | −179.7 (5) | N2—C7—C12—C11 | −177.8 (6) |
N2—N1—C4—C5 | 173.6 (5) | C16—C15A—C14—C15B | 26.8 (13) |
N2—N1—C4—C3 | −8.6 (7) | C16—C15A—C14—C2 | 124.0 (11) |
C3—C4—C5—C6 | 2.9 (9) | C16—C15B—C14—C15A | −23.0 (12) |
N1—C4—C5—C6 | −179.3 (5) | C16—C15B—C14—C2 | −125.2 (16) |
O1—C1—C6—C5 | 179.6 (5) | C1—C2—C14—C15A | 144.4 (7) |
C2—C1—C6—C5 | −2.0 (9) | C3—C2—C14—C15A | −35.1 (9) |
C4—C5—C6—C1 | −0.9 (9) | C1—C2—C14—C15B | −169.8 (11) |
N1—N2—C7—C8 | −158.7 (5) | C3—C2—C14—C15B | 10.7 (12) |
N1—N2—C7—C12 | 20.2 (8) | C14—C15A—C16—C15B | −26.8 (13) |
C12—C7—C8—C9 | −2.0 (9) | C14—C15B—C16—C15A | 24.2 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2 | 0.82 | 1.91 | 2.674 (6) | 155 |
O2—H1A···N1i | 0.87 (2) | 2.22 (12) | 2.908 (7) | 136 (14) |
O2—H1B···O1ii | 0.84 (2) | 2.17 (9) | 2.864 (6) | 140 (12) |
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x+1/2, −y+1/2, z−1/2. |