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The title molecule, C30H28N2O2, (I), resides on a crystallographic inversion centre located at the midpoint of the N—N bond. It contains an intra­molecular O—H...N inter­action [O...N = 2.572 (2) Å] and a weak C—H...N contact [C...N = 2.752 (2) Å]. There are no inter­molecular inter­actions of note in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044182/gg2038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044182/gg2038Isup2.hkl
Contains datablock I

CCDC reference: 663770

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.163
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.98 su
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 24
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 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 1 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

Comment top

Recently, a number of azine compounds containing both a diimine linkage and N—N bond have been investigated in terms of their crystallography and coordination chemistry (Kundu et al., 2005; Kesslen et al., 1999). As an extension of work on the structural characterization of azine derivatives, the title compound, (I),was synthesized and its crystal structure is reported here.

In the title compound (I), there is a crystallographic centre of symmetry at the midpoint of the N—N bond (Fig. 1). The molecule displays the (E,E) conformation with respect to the C8N1 and its symmetry related C8aN1a double bond (Fig. 1). This configuration agrees with those commonly found in similar compounds (Glaser et al., 1995; Hunig et al., 2000). The C6 aromatic rings in the asymmetric unit, C1–C6 (A), C10–C15 (B) have dihedral angles of 81.36 (7)°. The crystal structure is stabilized by intramolecular O—H···N hydrogen bonds and C—H···N contacts (Table 1).

Related literature top

For related literature, see: Glaser et al. (1995); Hunig et al. (2000); Kesslen et al. (1999); Kundu et al. (2005).

Experimental top

An ethanol solution (50 ml) of hydrazine (0.02 mol) and 1-(2-hydroxy-5-methylphenyl)-2-phenylethanone (0.04 mol) was refluxed and stirred for 5 h; the mixture was cooled and the resulting solid product, (I), was collected by filtration. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in acetone.

Refinement top

All H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H(methyl) = 0.96 Å, C—H(methylene) = 0.97 Å, C—H(aromatic) = 0.93 Å, O—H = 0.82 Å and with Uiso(H) =1.5Ueq(Cmethyl,O) and 1.2Ueq(Caromatic,Cmethylene).

Structure description top

Recently, a number of azine compounds containing both a diimine linkage and N—N bond have been investigated in terms of their crystallography and coordination chemistry (Kundu et al., 2005; Kesslen et al., 1999). As an extension of work on the structural characterization of azine derivatives, the title compound, (I),was synthesized and its crystal structure is reported here.

In the title compound (I), there is a crystallographic centre of symmetry at the midpoint of the N—N bond (Fig. 1). The molecule displays the (E,E) conformation with respect to the C8N1 and its symmetry related C8aN1a double bond (Fig. 1). This configuration agrees with those commonly found in similar compounds (Glaser et al., 1995; Hunig et al., 2000). The C6 aromatic rings in the asymmetric unit, C1–C6 (A), C10–C15 (B) have dihedral angles of 81.36 (7)°. The crystal structure is stabilized by intramolecular O—H···N hydrogen bonds and C—H···N contacts (Table 1).

For related literature, see: Glaser et al. (1995); Hunig et al. (2000); Kesslen et al. (1999); Kundu et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker,2005); data reduction: SAINT (Bruker,2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The molecular structure of compound (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines show intramolecular hydrogen bonds.
(E,E)-4,4'-Dimethyl-2,2'-(1,1'-dibenzylazino)diphenol top
Crystal data top
C30H28N2O2F(000) = 476
Mr = 448.54Dx = 1.254 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1572 reflections
a = 7.7881 (3) Åθ = 2.5–19.9°
b = 9.3199 (4) ŵ = 0.08 mm1
c = 16.5419 (6) ÅT = 273 K
β = 98.388 (2)°Plate, yellow
V = 1187.84 (8) Å30.32 × 0.23 × 0.12 mm
Z = 2
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2089 independent reflections
Radiation source: fine-focus sealed tube1435 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 99
Tmin = 0.989, Tmax = 0.992k = 1111
13182 measured reflectionsl = 1919
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.163 w = 1/[σ2(Fo2) + (0.106P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2089 reflectionsΔρmax = 0.16 e Å3
157 parametersΔρmin = 0.14 e Å3
24 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (7)
Crystal data top
C30H28N2O2V = 1187.84 (8) Å3
Mr = 448.54Z = 2
Monoclinic, P21/cMo Kα radiation
a = 7.7881 (3) ŵ = 0.08 mm1
b = 9.3199 (4) ÅT = 273 K
c = 16.5419 (6) Å0.32 × 0.23 × 0.12 mm
β = 98.388 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2089 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1435 reflections with I > 2σ(I)
Tmin = 0.989, Tmax = 0.992Rint = 0.049
13182 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04524 restraints
wR(F2) = 0.163H-atom parameters constrained
S = 1.01Δρmax = 0.16 e Å3
2089 reflectionsΔρmin = 0.14 e Å3
157 parameters
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
O11.0013 (2)0.69688 (17)0.65896 (9)0.0737 (5)
H11.02040.63070.62880.111*
N10.9839 (2)0.56036 (16)0.52287 (10)0.0502 (5)
C10.9186 (3)0.8041 (2)0.61378 (14)0.0568 (6)
C20.8747 (2)0.7964 (2)0.52817 (12)0.0492 (5)
C30.7900 (2)0.9149 (2)0.48862 (14)0.0543 (6)
H30.76090.91130.43210.065*
C40.7470 (3)1.0370 (2)0.52864 (15)0.0599 (6)
C50.7929 (3)1.0392 (3)0.61281 (17)0.0715 (7)
H50.76601.11970.64170.086*
C60.8768 (3)0.9260 (3)0.65486 (15)0.0697 (7)
H60.90570.93120.71130.084*
C70.6570 (3)1.1611 (2)0.48306 (18)0.0810 (8)
H7A0.60901.22260.52060.121*
H7B0.56561.12610.44260.121*
H7C0.73891.21420.45670.121*
C80.9139 (2)0.66973 (19)0.48152 (12)0.0463 (5)
C90.8695 (2)0.6714 (2)0.38985 (12)0.0508 (6)
H9A0.94170.60190.36700.061*
H9B0.89630.76540.36980.061*
C100.6811 (3)0.63753 (19)0.36001 (12)0.0477 (5)
C110.5936 (3)0.5321 (2)0.39669 (13)0.0589 (6)
H110.65070.48240.44150.071*
C120.4225 (3)0.4998 (3)0.36756 (17)0.0778 (8)
H120.36550.42800.39230.093*
C130.3372 (3)0.5736 (4)0.30232 (19)0.0886 (9)
H130.22220.55170.28260.106*
C140.4203 (4)0.6795 (3)0.26598 (17)0.0897 (9)
H140.36160.73000.22190.108*
C150.5920 (3)0.7115 (3)0.29474 (14)0.0694 (7)
H150.64790.78370.26980.083*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0905 (12)0.0692 (11)0.0575 (10)0.0016 (9)0.0020 (9)0.0031 (8)
N10.0501 (9)0.0438 (9)0.0543 (11)0.0025 (7)0.0004 (8)0.0038 (7)
C10.0570 (12)0.0534 (12)0.0603 (14)0.0109 (10)0.0097 (10)0.0054 (11)
C20.0435 (10)0.0463 (11)0.0585 (14)0.0085 (8)0.0093 (9)0.0027 (9)
C30.0500 (10)0.0498 (11)0.0644 (13)0.0069 (9)0.0123 (9)0.0007 (10)
C40.0519 (11)0.0489 (12)0.0824 (16)0.0081 (9)0.0213 (10)0.0055 (10)
C50.0699 (13)0.0583 (13)0.0920 (17)0.0088 (10)0.0316 (12)0.0157 (12)
C60.0760 (14)0.0721 (15)0.0638 (14)0.0137 (12)0.0191 (11)0.0151 (12)
C70.0686 (15)0.0512 (13)0.127 (2)0.0038 (11)0.0285 (15)0.0020 (14)
C80.0405 (10)0.0443 (11)0.0537 (13)0.0059 (8)0.0055 (9)0.0004 (9)
C90.0560 (11)0.0472 (11)0.0505 (13)0.0003 (9)0.0116 (9)0.0043 (9)
C100.0577 (11)0.0407 (10)0.0437 (11)0.0066 (9)0.0037 (9)0.0046 (9)
C110.0582 (12)0.0552 (13)0.0608 (14)0.0041 (10)0.0001 (11)0.0001 (10)
C120.0643 (15)0.0831 (17)0.0839 (19)0.0162 (13)0.0043 (14)0.0184 (15)
C130.0556 (14)0.116 (2)0.088 (2)0.0092 (15)0.0097 (15)0.0383 (19)
C140.0828 (19)0.116 (2)0.0616 (17)0.0375 (17)0.0189 (15)0.0110 (16)
C150.0849 (17)0.0682 (15)0.0530 (14)0.0157 (12)0.0027 (12)0.0064 (11)
Geometric parameters (Å, º) top
O1—C11.353 (3)C7—H7C0.9600
O1—H10.8200C8—C91.505 (3)
N1—C81.302 (2)C9—C101.512 (3)
N1—N1i1.399 (3)C9—H9A0.9700
C1—C61.387 (3)C9—H9B0.9700
C1—C21.409 (3)C10—C151.380 (3)
C2—C31.398 (3)C10—C111.385 (3)
C2—C81.467 (3)C11—C121.383 (3)
C3—C41.382 (3)C11—H110.9300
C3—H30.9300C12—C131.368 (4)
C4—C51.386 (3)C12—H120.9300
C4—C71.498 (3)C13—C141.367 (4)
C5—C61.375 (3)C13—H130.9300
C5—H50.9300C14—C151.385 (4)
C6—H60.9300C14—H140.9300
C7—H7A0.9600C15—H150.9300
C7—H7B0.9600
C1—O1—H1109.5N1—C8—C9123.66 (17)
C8—N1—N1i116.10 (19)C2—C8—C9119.12 (17)
O1—C1—C6117.5 (2)C8—C9—C10113.35 (15)
O1—C1—C2122.94 (18)C8—C9—H9A108.9
C6—C1—C2119.6 (2)C10—C9—H9A108.9
C3—C2—C1117.32 (19)C8—C9—H9B108.9
C3—C2—C8120.63 (19)C10—C9—H9B108.9
C1—C2—C8122.05 (18)H9A—C9—H9B107.7
C4—C3—C2123.8 (2)C15—C10—C11118.3 (2)
C4—C3—H3118.1C15—C10—C9120.29 (19)
C2—C3—H3118.1C11—C10—C9121.39 (17)
C3—C4—C5116.7 (2)C12—C11—C10120.8 (2)
C3—C4—C7121.5 (2)C12—C11—H11119.6
C5—C4—C7121.8 (2)C10—C11—H11119.6
C6—C5—C4122.0 (2)C13—C12—C11119.9 (3)
C6—C5—H5119.0C13—C12—H12120.1
C4—C5—H5119.0C11—C12—H12120.1
C5—C6—C1120.6 (2)C14—C13—C12120.2 (2)
C5—C6—H6119.7C14—C13—H13119.9
C1—C6—H6119.7C12—C13—H13119.9
C4—C7—H7A109.5C13—C14—C15120.0 (2)
C4—C7—H7B109.5C13—C14—H14120.0
H7A—C7—H7B109.5C15—C14—H14120.0
C4—C7—H7C109.5C10—C15—C14120.7 (3)
H7A—C7—H7C109.5C10—C15—H15119.6
H7B—C7—H7C109.5C14—C15—H15119.6
N1—C8—C2117.21 (18)
O1—C1—C2—C3179.72 (18)C1—C2—C8—N13.4 (3)
C6—C1—C2—C30.2 (3)C3—C2—C8—C92.9 (3)
O1—C1—C2—C80.7 (3)C1—C2—C8—C9177.61 (16)
C6—C1—C2—C8179.32 (18)N1—C8—C9—C1097.6 (2)
C1—C2—C3—C40.4 (3)C2—C8—C9—C1081.4 (2)
C8—C2—C3—C4179.19 (16)C8—C9—C10—C15140.17 (19)
C2—C3—C4—C50.3 (3)C8—C9—C10—C1140.1 (2)
C2—C3—C4—C7179.69 (19)C15—C10—C11—C121.3 (3)
C3—C4—C5—C60.1 (3)C9—C10—C11—C12178.43 (19)
C7—C4—C5—C6179.5 (2)C10—C11—C12—C130.8 (4)
C4—C5—C6—C10.1 (3)C11—C12—C13—C140.2 (4)
O1—C1—C6—C5179.9 (2)C12—C13—C14—C150.6 (4)
C2—C1—C6—C50.0 (3)C11—C10—C15—C141.0 (3)
N1i—N1—C8—C2178.47 (17)C9—C10—C15—C14178.8 (2)
N1i—N1—C8—C90.5 (3)C13—C14—C15—C100.0 (4)
C3—C2—C8—N1176.16 (16)
Symmetry code: (i) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.852.572 (2)146
C9—H9A···N1i0.972.372.752 (2)103
Symmetry code: (i) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC30H28N2O2
Mr448.54
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)7.7881 (3), 9.3199 (4), 16.5419 (6)
β (°) 98.388 (2)
V3)1187.84 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.32 × 0.23 × 0.12
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.989, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
13182, 2089, 1435
Rint0.049
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.163, 1.01
No. of reflections2089
No. of parameters157
No. of restraints24
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.14

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker,2005), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.8201.852.572 (2)146
C9—H9A···N1i0.9702.372.752 (2)103
Symmetry code: (i) x+2, y+1, z+1.
 

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