The title compound, C
13H
12N
2O, consisting of two aromatic groups linked through a diazene bridge, exhibits
trans geometry with respect to the azo double bond and deviates slightly from planarity. The crystal structure is stabilized by intermolecular O—H
N hydrogen bonds.
Supporting information
CCDC reference: 630510
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.160
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.106
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C13
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
1 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (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); software used to prepare material for publication: WinGX (Farrugia, 1999).
(
E)-4-(
p-Tolyldiazenyl}phenol
top
Crystal data top
C13H12N2O | F(000) = 448 |
Mr = 212.25 | Dx = 1.276 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 11243 reflections |
a = 5.6140 (5) Å | θ = 2.2–27.6° |
b = 17.8226 (14) Å | µ = 0.08 mm−1 |
c = 11.0657 (10) Å | T = 296 K |
β = 93.720 (7)° | Prism, yellow |
V = 1104.86 (16) Å3 | 0.34 × 0.29 × 0.24 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 1314 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.107 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
Detector resolution: 6.67 pixels mm-1 | h = −7→7 |
ω scans | k = −22→22 |
13022 measured reflections | l = −14→14 |
2519 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0743P)2] where P = (Fo2 + 2Fc2)/3 |
2519 reflections | (Δ/σ)max < 0.001 |
137 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
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 | |
O1 | 1.6795 (2) | 0.82504 (10) | 0.61940 (15) | 0.0699 (5) | |
N2 | 1.0258 (3) | 0.59731 (10) | 0.32600 (15) | 0.0576 (4) | |
C4 | 1.1976 (3) | 0.66814 (12) | 0.47573 (18) | 0.0591 (4) | |
N1 | 1.0235 (3) | 0.61368 (9) | 0.43558 (15) | 0.0591 (4) | |
C7 | 0.8529 (3) | 0.54132 (12) | 0.28706 (18) | 0.0576 (4) | |
C3 | 1.1616 (4) | 0.70095 (13) | 0.58647 (19) | 0.0637 (6) | |
H3 | 1.0302 | 0.6870 | 0.6283 | 0.076* | |
C1 | 1.5174 (3) | 0.77388 (11) | 0.57532 (17) | 0.0540 (5) | |
C6 | 1.5567 (3) | 0.74003 (13) | 0.46611 (19) | 0.0610 (5) | |
H6 | 1.6920 | 0.7526 | 0.4262 | 0.073* | |
C5 | 1.3991 (3) | 0.68806 (13) | 0.41540 (19) | 0.0610 (6) | |
H5 | 1.4266 | 0.6663 | 0.3412 | 0.073* | |
C10 | 0.5300 (4) | 0.43407 (12) | 0.1916 (2) | 0.0650 (6) | |
C2 | 1.3173 (3) | 0.75384 (12) | 0.63537 (19) | 0.0613 (6) | |
H2 | 1.2887 | 0.7763 | 0.7089 | 0.074* | |
C12 | 0.8630 (4) | 0.51589 (16) | 0.1706 (2) | 0.0824 (7) | |
H12 | 0.9783 | 0.5350 | 0.1223 | 0.099* | |
C9 | 0.5194 (4) | 0.45993 (14) | 0.3078 (2) | 0.0759 (7) | |
H9 | 0.4016 | 0.4414 | 0.3552 | 0.091* | |
C8 | 0.6781 (4) | 0.51262 (13) | 0.3567 (2) | 0.0721 (6) | |
H8 | 0.6677 | 0.5288 | 0.4361 | 0.087* | |
C13 | 0.3572 (4) | 0.37576 (14) | 0.1405 (2) | 0.0843 (8) | |
H13A | 0.3916 | 0.3646 | 0.0586 | 0.126* | |
H13B | 0.1972 | 0.3946 | 0.1419 | 0.126* | |
H13C | 0.3726 | 0.3309 | 0.1885 | 0.126* | |
C11 | 0.7055 (4) | 0.46260 (16) | 0.1240 (2) | 0.0822 (8) | |
H11 | 0.7181 | 0.4456 | 0.0452 | 0.099* | |
H1 | 1.634 (5) | 0.8474 (19) | 0.690 (3) | 0.124 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0602 (8) | 0.0861 (12) | 0.0630 (10) | −0.0074 (8) | 0.0009 (7) | −0.0152 (9) |
N2 | 0.0601 (7) | 0.0576 (8) | 0.0542 (8) | 0.0074 (6) | −0.0034 (5) | −0.0005 (6) |
C4 | 0.0639 (7) | 0.0575 (8) | 0.0548 (8) | 0.0046 (6) | −0.0041 (6) | −0.0005 (6) |
N1 | 0.0639 (7) | 0.0575 (8) | 0.0548 (8) | 0.0046 (6) | −0.0041 (6) | −0.0005 (6) |
C7 | 0.0601 (7) | 0.0576 (8) | 0.0542 (8) | 0.0074 (6) | −0.0034 (5) | −0.0005 (6) |
C3 | 0.0640 (11) | 0.0711 (14) | 0.0561 (13) | −0.0040 (10) | 0.0051 (9) | 0.0003 (11) |
C1 | 0.0526 (10) | 0.0580 (12) | 0.0504 (11) | 0.0069 (9) | −0.0049 (8) | −0.0015 (9) |
C6 | 0.0503 (10) | 0.0771 (14) | 0.0553 (12) | 0.0048 (10) | 0.0015 (8) | −0.0088 (11) |
C5 | 0.0607 (11) | 0.0703 (14) | 0.0510 (12) | 0.0136 (10) | −0.0033 (9) | −0.0108 (10) |
C10 | 0.0641 (12) | 0.0606 (13) | 0.0687 (15) | 0.0055 (10) | −0.0086 (10) | −0.0046 (11) |
C2 | 0.0645 (12) | 0.0710 (14) | 0.0487 (12) | 0.0000 (10) | 0.0047 (9) | −0.0031 (10) |
C12 | 0.0772 (14) | 0.1019 (19) | 0.0691 (16) | −0.0199 (14) | 0.0126 (11) | −0.0187 (14) |
C9 | 0.0861 (15) | 0.0723 (15) | 0.0698 (16) | −0.0185 (12) | 0.0104 (12) | −0.0021 (12) |
C8 | 0.0951 (16) | 0.0672 (14) | 0.0538 (14) | −0.0069 (12) | 0.0039 (12) | −0.0052 (11) |
C13 | 0.0802 (15) | 0.0747 (16) | 0.095 (2) | −0.0090 (12) | −0.0140 (13) | −0.0140 (14) |
C11 | 0.0834 (15) | 0.099 (2) | 0.0639 (15) | −0.0129 (14) | 0.0048 (12) | −0.0233 (14) |
Geometric parameters (Å, º) top
O1—C1 | 1.356 (2) | C5—H5 | 0.9300 |
O1—H1 | 0.93 (4) | C10—C9 | 1.371 (3) |
N2—N1 | 1.248 (2) | C10—C11 | 1.373 (3) |
N2—C7 | 1.439 (3) | C10—C13 | 1.507 (3) |
C4—C3 | 1.384 (3) | C2—H2 | 0.9300 |
C4—C5 | 1.396 (3) | C12—C11 | 1.375 (3) |
C4—N1 | 1.428 (3) | C12—H12 | 0.9300 |
C7—C12 | 1.371 (3) | C9—C8 | 1.381 (3) |
C7—C8 | 1.384 (3) | C9—H9 | 0.9300 |
C3—C2 | 1.372 (3) | C8—H8 | 0.9300 |
C3—H3 | 0.9300 | C13—H13A | 0.9600 |
C1—C6 | 1.381 (3) | C13—H13B | 0.9600 |
C1—C2 | 1.389 (3) | C13—H13C | 0.9600 |
C6—C5 | 1.375 (3) | C11—H11 | 0.9300 |
C6—H6 | 0.9300 | | |
| | | |
C1—O1—H1 | 112 (2) | C11—C10—C13 | 121.2 (2) |
N1—N2—C7 | 113.80 (18) | C3—C2—C1 | 120.2 (2) |
C3—C4—C5 | 119.01 (19) | C3—C2—H2 | 119.9 |
C3—C4—N1 | 115.2 (2) | C1—C2—H2 | 119.9 |
C5—C4—N1 | 125.70 (19) | C7—C12—C11 | 121.1 (2) |
N2—N1—C4 | 114.28 (18) | C7—C12—H12 | 119.5 |
C12—C7—C8 | 118.4 (2) | C11—C12—H12 | 119.5 |
C12—C7—N2 | 116.3 (2) | C10—C9—C8 | 122.0 (2) |
C8—C7—N2 | 125.35 (19) | C10—C9—H9 | 119.0 |
C2—C3—C4 | 120.9 (2) | C8—C9—H9 | 119.0 |
C2—C3—H3 | 119.6 | C9—C8—C7 | 119.7 (2) |
C4—C3—H3 | 119.6 | C9—C8—H8 | 120.1 |
O1—C1—C6 | 117.83 (19) | C7—C8—H8 | 120.1 |
O1—C1—C2 | 123.06 (19) | C10—C13—H13A | 109.5 |
C6—C1—C2 | 119.11 (19) | C10—C13—H13B | 109.5 |
C5—C6—C1 | 121.1 (2) | H13A—C13—H13B | 109.5 |
C5—C6—H6 | 119.5 | C10—C13—H13C | 109.5 |
C1—C6—H6 | 119.5 | H13A—C13—H13C | 109.5 |
C6—C5—C4 | 119.7 (2) | H13B—C13—H13C | 109.5 |
C6—C5—H5 | 120.1 | C10—C11—C12 | 121.2 (2) |
C4—C5—H5 | 120.1 | C10—C11—H11 | 119.4 |
C9—C10—C11 | 117.6 (2) | C12—C11—H11 | 119.4 |
C9—C10—C13 | 121.2 (2) | | |
| | | |
C7—N2—N1—C4 | 178.85 (15) | O1—C1—C2—C3 | −179.21 (18) |
C3—C4—N1—N2 | 164.55 (17) | C6—C1—C2—C3 | 0.1 (3) |
C5—C4—N1—N2 | −17.8 (3) | C8—C7—C12—C11 | −0.7 (4) |
N1—N2—C7—C12 | −173.87 (19) | N2—C7—C12—C11 | −179.8 (2) |
N1—N2—C7—C8 | 7.1 (3) | C11—C10—C9—C8 | −0.1 (4) |
C5—C4—C3—C2 | 1.8 (3) | C13—C10—C9—C8 | 179.2 (2) |
N1—C4—C3—C2 | 179.61 (18) | C10—C9—C8—C7 | 0.7 (4) |
O1—C1—C6—C5 | −179.48 (18) | C12—C7—C8—C9 | −0.2 (4) |
C2—C1—C6—C5 | 1.1 (3) | N2—C7—C8—C9 | 178.7 (2) |
C1—C6—C5—C4 | −1.0 (3) | C9—C10—C11—C12 | −0.8 (4) |
C3—C4—C5—C6 | −0.5 (3) | C13—C10—C11—C12 | 179.9 (2) |
N1—C4—C5—C6 | −178.09 (18) | C7—C12—C11—C10 | 1.2 (4) |
C4—C3—C2—C1 | −1.6 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.93 (4) | 1.93 (4) | 2.853 (2) | 174 (3) |
Symmetry code: (i) x+1/2, −y+3/2, z+1/2. |