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The oxidation of 4-hydroxy­azo­benzene provided a mixture of two azoxy compounds, which were separated by column chromatography. The isomer with the higher melting point appeared to belong to the α (ONN) series, as determined by X-ray diffraction. The mol­ecule, C12H10N2O2, is almost planar. The benzene rings are twisted by 11.7 (2) (substituted) and 4.1 (1)° (unsubstituted) with respect to the ONN plane. The mol­ecules are connected to one another by strong O—H...O hydrogen bonds forming chains extended along [001], which are bound by much weaker C—H...O hydrogen bonds forming layers in the bc plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003449/gd1082sup1.cif
Contains datablocks global, IIa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003449/gd1082IIasup2.hkl
Contains datablock IIa

CCDC reference: 146061

Computing details top

Data collection: KUMA Diffraction Software (Kuma, 1998); cell refinement: KUMA Diffraction Software; data reduction: KUMA Diffraction Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

(IIa) top
Crystal data top
C12H10N2O2Dx = 1.372 Mg m3
Dm = 1.37 (1) Mg m3
Dm measured by flotation
Mr = 214.22Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 21 reflections
a = 7.187 (1) Åθ = 8–11°
b = 11.261 (2) ŵ = 0.10 mm1
c = 12.812 (3) ÅT = 293 K
V = 1036.9 (3) Å3Plate, yellow
Z = 40.5 × 0.4 × 0.3 mm
F(000) = 448
Data collection top
KUMA KM–4
diffractometer
Rint = 0.029
Radiation source: fine-focus sealed tubeθmax = 30.1°, θmin = 2.4°
Graphite monochromatorh = 1010
ωθ scansk = 1515
2796 measured reflectionsl = 1818
1729 independent reflections2 standard reflections every 50 reflections
1026 reflections with I > 2σ(I) intensity decay: 0.5%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: difference Fourier map
wR(F2) = 0.096All H atoms refined isotropically
S = 0.99Calculated w = 1/[σ2(Fo2) + (0.0252P)2 + 0.113P]
where P = (Fo2 + 2Fc2)/3
1729 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.13 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N20.2024 (3)0.24506 (17)0.84313 (14)0.0548 (5)
N10.1457 (3)0.21220 (18)0.93209 (14)0.0521 (5)
O20.2274 (3)0.70176 (16)0.68493 (14)0.0673 (6)
O10.0781 (3)0.27976 (13)1.00334 (14)0.0608 (5)
C10.1961 (4)0.3645 (2)0.81248 (16)0.0514 (6)
C20.2936 (4)0.3844 (2)0.72042 (17)0.0634 (7)
C30.3056 (4)0.4951 (2)0.67680 (18)0.0626 (7)
C40.2184 (4)0.5901 (2)0.72317 (16)0.0523 (6)
C50.1148 (4)0.5715 (2)0.81343 (18)0.0569 (7)
C60.1035 (4)0.4607 (2)0.85810 (17)0.0544 (6)
C1'0.1562 (3)0.0855 (2)0.95302 (16)0.0491 (6)
C6'0.1027 (4)0.0457 (2)1.04995 (19)0.0619 (7)
C5'0.1099 (5)0.0739 (3)1.0707 (2)0.0736 (9)
C4'0.1677 (5)0.1527 (3)0.9970 (2)0.0719 (8)
C3'0.2199 (5)0.1121 (2)0.89940 (19)0.0722 (8)
C2'0.2135 (4)0.0072 (3)0.87713 (19)0.0625 (7)
H220.298 (6)0.703 (3)0.632 (3)0.108 (12)*
H20.370 (5)0.315 (3)0.686 (3)0.098 (10)*
H30.375 (4)0.506 (2)0.618 (2)0.071 (8)*
H50.045 (3)0.639 (2)0.8410 (18)0.061 (7)*
H60.026 (4)0.445 (2)0.920 (2)0.066 (8)*
H6'0.059 (4)0.105 (2)1.096 (2)0.080 (9)*
H5'0.059 (5)0.105 (3)1.135 (3)0.123 (13)*
H4'0.163 (4)0.236 (2)1.008 (2)0.068 (7)*
H3'0.254 (4)0.171 (2)0.848 (2)0.093 (10)*
H2'0.246 (4)0.038 (2)0.808 (2)0.074 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0612 (13)0.0648 (13)0.0383 (9)0.0017 (12)0.0060 (10)0.0019 (9)
N10.0550 (12)0.0659 (13)0.0355 (8)0.0005 (11)0.0017 (9)0.0047 (9)
O20.0893 (15)0.0617 (11)0.0508 (9)0.0053 (11)0.0132 (10)0.0078 (8)
O10.0805 (12)0.0664 (11)0.0353 (6)0.0122 (10)0.0062 (9)0.0081 (9)
C10.0620 (15)0.0522 (13)0.0399 (10)0.0017 (13)0.0015 (12)0.0011 (10)
C20.0830 (19)0.0648 (15)0.0423 (11)0.0008 (16)0.0122 (14)0.0039 (11)
C30.0787 (19)0.0697 (17)0.0394 (11)0.0032 (16)0.0133 (14)0.0017 (12)
C40.0625 (15)0.0578 (14)0.0367 (10)0.0004 (13)0.0017 (11)0.0029 (10)
C50.0637 (16)0.0615 (15)0.0454 (12)0.0065 (14)0.0071 (13)0.0009 (11)
C60.0569 (15)0.0663 (16)0.0400 (11)0.0009 (13)0.0064 (12)0.0009 (11)
C1'0.0537 (15)0.0526 (14)0.0410 (11)0.0003 (12)0.0029 (11)0.0019 (10)
C6'0.0772 (19)0.0671 (17)0.0414 (12)0.0005 (15)0.0088 (14)0.0037 (12)
C5'0.106 (3)0.0663 (17)0.0486 (13)0.0125 (18)0.0102 (17)0.0082 (13)
C4'0.101 (2)0.0572 (15)0.0577 (14)0.0097 (17)0.0046 (18)0.0062 (14)
C3'0.101 (2)0.0612 (16)0.0546 (14)0.0033 (17)0.0127 (17)0.0036 (13)
C2'0.0796 (19)0.0662 (16)0.0417 (11)0.0044 (16)0.0087 (14)0.0024 (12)
Geometric parameters (Å, º) top
N2—N11.266 (3)C4—C51.391 (3)
N2—C11.402 (3)C5—C61.375 (3)
N1—O11.284 (2)C1'—C6'1.375 (3)
N1—C1'1.453 (3)C1'—C2'1.376 (3)
O2—C41.351 (3)C6'—C5'1.375 (4)
C1—C21.390 (3)C5'—C4'1.359 (4)
C1—C61.400 (3)C4'—C3'1.383 (4)
C2—C31.368 (4)C3'—C2'1.375 (4)
C3—C41.375 (3)
N1—N2—C1121.5 (2)C3—C4—C5119.1 (2)
N2—N1—O1126.1 (2)C6—C5—C4120.9 (2)
N2—N1—C1'115.9 (2)C5—C6—C1120.0 (2)
O1—N1—C1'118.0 (2)C6'—C1'—C2'120.9 (2)
C2—C1—C6118.0 (2)C6'—C1'—N1118.2 (2)
C2—C1—N2112.1 (2)C2'—C1'—N1120.9 (2)
C6—C1—N2129.9 (2)C1'—C6'—C5'118.9 (2)
C3—C2—C1121.7 (3)C4'—C5'—C6'121.1 (2)
C2—C3—C4120.2 (2)C5'—C4'—C3'119.7 (3)
O2—C4—C3123.1 (2)C2'—C3'—C4'120.1 (3)
O2—C4—C5117.8 (2)C1'—C2'—C3'119.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H22···O1i0.85 (4)1.88 (4)2.722 (3)170 (4)
C3—H3···O2ii0.97 (3)2.54 (3)3.456 (3)158 (3)
Symmetry codes: (i) x+1/2, y+1, z1/2; (ii) x, y1, z.
Selected geometric paramterers in some substituted azoxybenzenes top
4-OH4,4'-(OMe)24,4'-(OPr)24'-N(Me)2cis-4'-Me
N1-N21.266 (3)1.2811.2551.2631.264
N1-O11.284 (2)1.2881.2711.2751.264
C1-N21.402 (3)1.4281.4211.4151.427
C1'-N11.453 (3)1.4451.4751.4421.470
C1'-N1-O1118.0 (2)118.9115.7114.6114.3
C1'-N1-N2115.9 (2)116.5116.0118.4125.0
N2-N1-O1126.1 (2)124.6128.3126.7120.5
C1-N2-N1121.5 (2)120.6118.8118.8119.2
C2-C1-N2112.1 (2)112.7112.5112.6116.5
C6-C1-N2129.9 (2)127.5130.0127.8123.4
C2'-C1'-N1120.9 (2)120.7122.2120.4119.0
C6'-C1'-N1118.2 (2)119.5117.2119.8118.3
A\dag/B4.1 (1)3.34.08.955.5
B/C11.7 (2)19.46.333.456.6
A/C15.6 (1)22.22.332.669.9
\dag The angle between the planes defined as: A the plane of the benzene ring connected to the atom N1; B the plane of the azoxy group; C the plane of the other benzene ring.
 

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