Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044182/gg2038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044182/gg2038Isup2.hkl |
CCDC reference: 663770
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (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
For related literature, see: Glaser et al. (1995); Hunig et al. (2000); Kesslen et al. (1999); Kundu et al. (2005).
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.
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).
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 C8═N1 and its symmetry related C8a═N1a 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).
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).
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. |
C30H28N2O2 | F(000) = 476 |
Mr = 448.54 | Dx = 1.254 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1572 reflections |
a = 7.7881 (3) Å | θ = 2.5–19.9° |
b = 9.3199 (4) Å | µ = 0.08 mm−1 |
c = 16.5419 (6) Å | T = 273 K |
β = 98.388 (2)° | Plate, yellow |
V = 1187.84 (8) Å3 | 0.32 × 0.23 × 0.12 mm |
Z = 2 |
Bruker APEXII CCD area-detector diffractometer | 2089 independent reflections |
Radiation source: fine-focus sealed tube | 1435 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
φ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −9→9 |
Tmin = 0.989, Tmax = 0.992 | k = −11→11 |
13182 measured reflections | l = −19→19 |
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)] = 0.045 | H-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 reflections | Δρmax = 0.16 e Å−3 |
157 parameters | Δρmin = −0.14 e Å−3 |
24 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.026 (7) |
C30H28N2O2 | V = 1187.84 (8) Å3 |
Mr = 448.54 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.7881 (3) Å | µ = 0.08 mm−1 |
b = 9.3199 (4) Å | T = 273 K |
c = 16.5419 (6) Å | 0.32 × 0.23 × 0.12 mm |
β = 98.388 (2)° |
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 = 0.992 | Rint = 0.049 |
13182 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 24 restraints |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.16 e Å−3 |
2089 reflections | Δρmin = −0.14 e Å−3 |
157 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.0013 (2) | 0.69688 (17) | 0.65896 (9) | 0.0737 (5) | |
H1 | 1.0204 | 0.6307 | 0.6288 | 0.111* | |
N1 | 0.9839 (2) | 0.56036 (16) | 0.52287 (10) | 0.0502 (5) | |
C1 | 0.9186 (3) | 0.8041 (2) | 0.61378 (14) | 0.0568 (6) | |
C2 | 0.8747 (2) | 0.7964 (2) | 0.52817 (12) | 0.0492 (5) | |
C3 | 0.7900 (2) | 0.9149 (2) | 0.48862 (14) | 0.0543 (6) | |
H3 | 0.7609 | 0.9113 | 0.4321 | 0.065* | |
C4 | 0.7470 (3) | 1.0370 (2) | 0.52864 (15) | 0.0599 (6) | |
C5 | 0.7929 (3) | 1.0392 (3) | 0.61281 (17) | 0.0715 (7) | |
H5 | 0.7660 | 1.1197 | 0.6417 | 0.086* | |
C6 | 0.8768 (3) | 0.9260 (3) | 0.65486 (15) | 0.0697 (7) | |
H6 | 0.9057 | 0.9312 | 0.7113 | 0.084* | |
C7 | 0.6570 (3) | 1.1611 (2) | 0.48306 (18) | 0.0810 (8) | |
H7A | 0.6090 | 1.2226 | 0.5206 | 0.121* | |
H7B | 0.5656 | 1.1261 | 0.4426 | 0.121* | |
H7C | 0.7389 | 1.2142 | 0.4567 | 0.121* | |
C8 | 0.9139 (2) | 0.66973 (19) | 0.48152 (12) | 0.0463 (5) | |
C9 | 0.8695 (2) | 0.6714 (2) | 0.38985 (12) | 0.0508 (6) | |
H9A | 0.9417 | 0.6019 | 0.3670 | 0.061* | |
H9B | 0.8963 | 0.7654 | 0.3698 | 0.061* | |
C10 | 0.6811 (3) | 0.63753 (19) | 0.36001 (12) | 0.0477 (5) | |
C11 | 0.5936 (3) | 0.5321 (2) | 0.39669 (13) | 0.0589 (6) | |
H11 | 0.6507 | 0.4824 | 0.4415 | 0.071* | |
C12 | 0.4225 (3) | 0.4998 (3) | 0.36756 (17) | 0.0778 (8) | |
H12 | 0.3655 | 0.4280 | 0.3923 | 0.093* | |
C13 | 0.3372 (3) | 0.5736 (4) | 0.30232 (19) | 0.0886 (9) | |
H13 | 0.2222 | 0.5517 | 0.2826 | 0.106* | |
C14 | 0.4203 (4) | 0.6795 (3) | 0.26598 (17) | 0.0897 (9) | |
H14 | 0.3616 | 0.7300 | 0.2219 | 0.108* | |
C15 | 0.5920 (3) | 0.7115 (3) | 0.29474 (14) | 0.0694 (7) | |
H15 | 0.6479 | 0.7837 | 0.2698 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0905 (12) | 0.0692 (11) | 0.0575 (10) | −0.0016 (9) | −0.0020 (9) | −0.0031 (8) |
N1 | 0.0501 (9) | 0.0438 (9) | 0.0543 (11) | −0.0025 (7) | −0.0004 (8) | −0.0038 (7) |
C1 | 0.0570 (12) | 0.0534 (12) | 0.0603 (14) | −0.0109 (10) | 0.0097 (10) | −0.0054 (11) |
C2 | 0.0435 (10) | 0.0463 (11) | 0.0585 (14) | −0.0085 (8) | 0.0093 (9) | −0.0027 (9) |
C3 | 0.0500 (10) | 0.0498 (11) | 0.0644 (13) | −0.0069 (9) | 0.0123 (9) | −0.0007 (10) |
C4 | 0.0519 (11) | 0.0489 (12) | 0.0824 (16) | −0.0081 (9) | 0.0213 (10) | −0.0055 (10) |
C5 | 0.0699 (13) | 0.0583 (13) | 0.0920 (17) | −0.0088 (10) | 0.0316 (12) | −0.0157 (12) |
C6 | 0.0760 (14) | 0.0721 (15) | 0.0638 (14) | −0.0137 (12) | 0.0191 (11) | −0.0151 (12) |
C7 | 0.0686 (15) | 0.0512 (13) | 0.127 (2) | 0.0038 (11) | 0.0285 (15) | 0.0020 (14) |
C8 | 0.0405 (10) | 0.0443 (11) | 0.0537 (13) | −0.0059 (8) | 0.0055 (9) | −0.0004 (9) |
C9 | 0.0560 (11) | 0.0472 (11) | 0.0505 (13) | 0.0003 (9) | 0.0116 (9) | 0.0043 (9) |
C10 | 0.0577 (11) | 0.0407 (10) | 0.0437 (11) | 0.0066 (9) | 0.0037 (9) | −0.0046 (9) |
C11 | 0.0582 (12) | 0.0552 (13) | 0.0608 (14) | −0.0041 (10) | 0.0001 (11) | −0.0001 (10) |
C12 | 0.0643 (15) | 0.0831 (17) | 0.0839 (19) | −0.0162 (13) | 0.0043 (14) | −0.0184 (15) |
C13 | 0.0556 (14) | 0.116 (2) | 0.088 (2) | 0.0092 (15) | −0.0097 (15) | −0.0383 (19) |
C14 | 0.0828 (19) | 0.116 (2) | 0.0616 (17) | 0.0375 (17) | −0.0189 (15) | −0.0110 (16) |
C15 | 0.0849 (17) | 0.0682 (15) | 0.0530 (14) | 0.0157 (12) | 0.0027 (12) | 0.0064 (11) |
O1—C1 | 1.353 (3) | C7—H7C | 0.9600 |
O1—H1 | 0.8200 | C8—C9 | 1.505 (3) |
N1—C8 | 1.302 (2) | C9—C10 | 1.512 (3) |
N1—N1i | 1.399 (3) | C9—H9A | 0.9700 |
C1—C6 | 1.387 (3) | C9—H9B | 0.9700 |
C1—C2 | 1.409 (3) | C10—C15 | 1.380 (3) |
C2—C3 | 1.398 (3) | C10—C11 | 1.385 (3) |
C2—C8 | 1.467 (3) | C11—C12 | 1.383 (3) |
C3—C4 | 1.382 (3) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.368 (4) |
C4—C5 | 1.386 (3) | C12—H12 | 0.9300 |
C4—C7 | 1.498 (3) | C13—C14 | 1.367 (4) |
C5—C6 | 1.375 (3) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—C15 | 1.385 (4) |
C6—H6 | 0.9300 | C14—H14 | 0.9300 |
C7—H7A | 0.9600 | C15—H15 | 0.9300 |
C7—H7B | 0.9600 | ||
C1—O1—H1 | 109.5 | N1—C8—C9 | 123.66 (17) |
C8—N1—N1i | 116.10 (19) | C2—C8—C9 | 119.12 (17) |
O1—C1—C6 | 117.5 (2) | C8—C9—C10 | 113.35 (15) |
O1—C1—C2 | 122.94 (18) | C8—C9—H9A | 108.9 |
C6—C1—C2 | 119.6 (2) | C10—C9—H9A | 108.9 |
C3—C2—C1 | 117.32 (19) | C8—C9—H9B | 108.9 |
C3—C2—C8 | 120.63 (19) | C10—C9—H9B | 108.9 |
C1—C2—C8 | 122.05 (18) | H9A—C9—H9B | 107.7 |
C4—C3—C2 | 123.8 (2) | C15—C10—C11 | 118.3 (2) |
C4—C3—H3 | 118.1 | C15—C10—C9 | 120.29 (19) |
C2—C3—H3 | 118.1 | C11—C10—C9 | 121.39 (17) |
C3—C4—C5 | 116.7 (2) | C12—C11—C10 | 120.8 (2) |
C3—C4—C7 | 121.5 (2) | C12—C11—H11 | 119.6 |
C5—C4—C7 | 121.8 (2) | C10—C11—H11 | 119.6 |
C6—C5—C4 | 122.0 (2) | C13—C12—C11 | 119.9 (3) |
C6—C5—H5 | 119.0 | C13—C12—H12 | 120.1 |
C4—C5—H5 | 119.0 | C11—C12—H12 | 120.1 |
C5—C6—C1 | 120.6 (2) | C14—C13—C12 | 120.2 (2) |
C5—C6—H6 | 119.7 | C14—C13—H13 | 119.9 |
C1—C6—H6 | 119.7 | C12—C13—H13 | 119.9 |
C4—C7—H7A | 109.5 | C13—C14—C15 | 120.0 (2) |
C4—C7—H7B | 109.5 | C13—C14—H14 | 120.0 |
H7A—C7—H7B | 109.5 | C15—C14—H14 | 120.0 |
C4—C7—H7C | 109.5 | C10—C15—C14 | 120.7 (3) |
H7A—C7—H7C | 109.5 | C10—C15—H15 | 119.6 |
H7B—C7—H7C | 109.5 | C14—C15—H15 | 119.6 |
N1—C8—C2 | 117.21 (18) | ||
O1—C1—C2—C3 | −179.72 (18) | C1—C2—C8—N1 | 3.4 (3) |
C6—C1—C2—C3 | 0.2 (3) | C3—C2—C8—C9 | 2.9 (3) |
O1—C1—C2—C8 | 0.7 (3) | C1—C2—C8—C9 | −177.61 (16) |
C6—C1—C2—C8 | −179.32 (18) | N1—C8—C9—C10 | 97.6 (2) |
C1—C2—C3—C4 | −0.4 (3) | C2—C8—C9—C10 | −81.4 (2) |
C8—C2—C3—C4 | 179.19 (16) | C8—C9—C10—C15 | 140.17 (19) |
C2—C3—C4—C5 | 0.3 (3) | C8—C9—C10—C11 | −40.1 (2) |
C2—C3—C4—C7 | 179.69 (19) | C15—C10—C11—C12 | 1.3 (3) |
C3—C4—C5—C6 | −0.1 (3) | C9—C10—C11—C12 | −178.43 (19) |
C7—C4—C5—C6 | −179.5 (2) | C10—C11—C12—C13 | −0.8 (4) |
C4—C5—C6—C1 | −0.1 (3) | C11—C12—C13—C14 | −0.2 (4) |
O1—C1—C6—C5 | 179.9 (2) | C12—C13—C14—C15 | 0.6 (4) |
C2—C1—C6—C5 | 0.0 (3) | C11—C10—C15—C14 | −1.0 (3) |
N1i—N1—C8—C2 | 178.47 (17) | C9—C10—C15—C14 | 178.8 (2) |
N1i—N1—C8—C9 | −0.5 (3) | C13—C14—C15—C10 | 0.0 (4) |
C3—C2—C8—N1 | −176.16 (16) |
Symmetry code: (i) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.85 | 2.572 (2) | 146 |
C9—H9A···N1i | 0.97 | 2.37 | 2.752 (2) | 103 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C30H28N2O2 |
Mr | 448.54 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 7.7881 (3), 9.3199 (4), 16.5419 (6) |
β (°) | 98.388 (2) |
V (Å3) | 1187.84 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.32 × 0.23 × 0.12 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.989, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13182, 2089, 1435 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.163, 1.01 |
No. of reflections | 2089 |
No. of parameters | 157 |
No. of restraints | 24 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.14 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker,2005), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.820 | 1.85 | 2.572 (2) | 146 |
C9—H9A···N1i | 0.970 | 2.37 | 2.752 (2) | 103 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
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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 C8═N1 and its symmetry related C8a═N1a 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).