organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(E)-2-[(3,5-Di-tert-butyl-2-hy­droxy­benzyl­­idene)amino]benzo­nitrile

aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China
*Correspondence e-mail: jczhou@seu.edu.cn

(Received 15 May 2009; accepted 22 May 2009; online 29 May 2009)

The asymmetric unit of the title compound, C22H26N2O, contains three crystallographically independent mol­ecules, in which the aromatic rings are oriented at dihedral angles of 21.74 (5), 27.59 (5) and 27.87 (5)°. Intra­molecular O—H⋯N hydrogen bonds result in the formation of planar six-membered rings, and these are nearly coplanar with the adjacent rings. In the crystal structure, ππ contacts between the benzene rings [centroid–centroid distances = 3.989 (2), 3.802 (1) and 3.882 (1) Å] may stabilize the structure.

Related literature

For general background, see: Chen et al. (2008[Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170-2171.]); Dao et al. (2000[Dao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805-813.]); Sriram et al. (2006[Sriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127-2129.]); Weber et al. (2007[Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159-1162.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C22H26N2O

  • Mr = 334.45

  • Monoclinic, P 21 /c

  • a = 27.9710 (4) Å

  • b = 7.32780 (11) Å

  • c = 29.7840 (4) Å

  • β = 104.5330 (2)°

  • V = 5909.37 (15) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 294 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.948, Tmax = 0.986

  • 30875 measured reflections

  • 11513 independent reflections

  • 4685 reflections with I > 2σ(I)

  • Rint = 0.130

Refinement
  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 0.173

  • S = 0.81

  • 11513 reflections

  • 689 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3A⋯N5 0.95 (2) 1.81 (2) 2.622 (2) 143 (2)
O2—H2A⋯N3 0.92 (3) 1.82 (3) 2.615 (2) 143 (2)
O1—H1A⋯N1 0.87 (2) 1.86 (2) 2.623 (2) 145 (2)

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Schiff base compounds have received considerable attention for many years, primarily due to various pharmacological activities, such as anticancer (Dao et al., 2000) and anti-HIV (Sriram et al., 2006). In addition, Schiff base compounds play important roles in the development of coordination chemistry related to magnetism (Weber, et al., 2007) and catalysis (Chen, et al., 2008). We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains three crystallographicaly independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (C16-C21), C (C23-C28), D (C38-C43), E (C45-C50) and F (C60-C65) are, of course, planar and the dihedral angles between them are A/B = 21.74 (5), C/D = 27.59 (5) and E/F = 27.87 (5) °. Intramolecular O-H···N hydrogen bonds (Table 1) results in the formations of planar six-membered rings G (O1/N1/C1/C2/H1A), H (O2/N3/C23/C24/C37/H2A) and I (O3/N5/C45/C50/C59/H3A), in which they are oriented with respect to the adjacent rings at dihedral angles of A/G = 1.23 (5), C/H = 1.07 (5) and E/I = 1.30 (5) °.

In the crystal structure, the ππ contacts between the benzene rings, Cg1—Cg4i, Cg2—Cg3i and Cg5—Cg6ii, [symmetry codes: (i) x, y - 1, z, (ii) 1 - x, 1/2 + y, 1/2 - z, where Cg1, Cg2, Cg3, Cg4, Cg5 and Cg6 are centroids of the rings A (C1-C6), B (C16-C21), C (C23-C28), D (C38-C43), E (C45-C50) and F (C60-C65), respectively] may stabilize the structure, with centroid-centroid distances of 3.989 (2), 3.802 (1) and 3.882 (1) Å, respectively.

Related literature top

For general background, see: Chen et al. (2008); Dao et al. (2000); Sriram et al. (2006); Weber et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 3,5-di-tert-butyl-2 -hydroxybenzaldehyde (0.936 g, 4 mmol) and 2-aminobenzonitrile (0.531 g, 4.5 mmol) were dissolved in ethanol (25 ml). The mixture was heated to reflux for 6 h, and then cooled to room temperature. The solution was filtered and yellow crystals suitable for X-ray analysis formed after two weeks on slow evaporation of the solvent at room temperature.

Refinement top

H atoms (for OH) were located in a difference synthesis and refined isotropically. The remaining H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms have been omitted for clarity.
(E)-2-[(3,5-Di-tert-butyl-2-hydroxybenzylidene)amino]benzonitrile top
Crystal data top
C22H26N2OF(000) = 2160
Mr = 334.45Dx = 1.128 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2369 reflections
a = 27.9710 (4) Åθ = 3.1–27.0°
b = 7.32780 (11) ŵ = 0.07 mm1
c = 29.7840 (4) ÅT = 294 K
β = 104.5330 (2)°Block, yellow
V = 5909.37 (15) Å30.30 × 0.20 × 0.20 mm
Z = 12
Data collection top
Bruker SMART CCD area-detector
diffractometer
11513 independent reflections
Radiation source: fine-focus sealed tube4685 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.130
ϕ and ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: empirical (using intensity measurements)
(SADABS; Bruker, 2000)
h = 3234
Tmin = 0.948, Tmax = 0.986k = 89
30875 measured reflectionsl = 3627
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)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.173 w = 1/[σ2(Fo2) + (0.0618P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.81(Δ/σ)max < 0.001
11513 reflectionsΔρmax = 0.31 e Å3
689 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00170 (18)
Crystal data top
C22H26N2OV = 5909.37 (15) Å3
Mr = 334.45Z = 12
Monoclinic, P21/cMo Kα radiation
a = 27.9710 (4) ŵ = 0.07 mm1
b = 7.32780 (11) ÅT = 294 K
c = 29.7840 (4) Å0.30 × 0.20 × 0.20 mm
β = 104.5330 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
11513 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Bruker, 2000)
4685 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.986Rint = 0.130
30875 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.173H atoms treated by a mixture of independent and constrained refinement
S = 0.81Δρmax = 0.31 e Å3
11513 reflectionsΔρmin = 0.23 e Å3
689 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
O10.15087 (5)0.3744 (2)0.18806 (5)0.0691 (5)
H1A0.1686 (9)0.398 (4)0.1684 (8)0.096 (10)*
O20.18374 (5)0.9439 (2)0.02043 (5)0.0684 (5)
H2A0.1652 (9)0.925 (4)0.0006 (9)0.116 (11)*
O30.48619 (5)0.9288 (2)0.35466 (5)0.0684 (5)
H3A0.5055 (9)0.923 (3)0.3328 (8)0.099 (9)*
N10.16759 (6)0.4172 (2)0.10588 (6)0.0550 (5)
N20.27218 (8)0.5702 (4)0.18410 (8)0.1010 (8)
N30.16614 (6)0.9441 (2)0.06174 (6)0.0520 (5)
N40.05724 (8)1.1104 (3)0.00802 (8)0.0945 (8)
N50.50291 (6)0.9533 (2)0.27211 (6)0.0541 (5)
N60.60959 (8)1.1213 (4)0.34472 (8)0.1030 (9)
C10.08638 (7)0.4080 (3)0.11845 (7)0.0515 (6)
C20.10180 (7)0.3837 (3)0.16714 (7)0.0549 (6)
C30.06760 (7)0.3746 (3)0.19363 (7)0.0544 (6)
C40.01780 (7)0.3800 (3)0.17000 (7)0.0594 (6)
H4A0.00560.37310.18730.071*
C50.00084 (7)0.3952 (3)0.12154 (7)0.0555 (6)
C60.03561 (7)0.4134 (3)0.09736 (7)0.0567 (6)
H6A0.02540.43010.06540.068*
C70.05489 (8)0.3915 (4)0.09889 (8)0.0686 (7)
C80.07643 (9)0.2160 (5)0.11300 (10)0.1213 (12)
H8A0.07120.21300.14610.182*
H8B0.06050.11290.10310.182*
H8C0.11120.21150.09870.182*
C90.07904 (9)0.5588 (5)0.11231 (11)0.1360 (15)
H9A0.06430.66570.10280.204*
H9B0.07450.56080.14530.204*
H9C0.11370.55670.09740.204*
C100.06546 (8)0.3877 (4)0.04606 (8)0.0917 (9)
H10A0.05280.49680.03540.138*
H10B0.10050.38080.03300.138*
H10C0.04980.28320.03660.138*
C110.08366 (8)0.3572 (3)0.24710 (7)0.0606 (6)
C120.11144 (8)0.1771 (4)0.26034 (8)0.0839 (8)
H12A0.09050.07710.24700.126*
H12B0.12070.16500.29350.126*
H12C0.14050.17640.24880.126*
C130.11663 (9)0.5200 (4)0.26765 (8)0.0828 (8)
H13A0.09880.63160.25890.124*
H13B0.14570.51980.25610.124*
H13C0.12600.51010.30080.124*
C140.03994 (8)0.3589 (3)0.26913 (7)0.0759 (7)
H14A0.01840.25860.25730.114*
H14B0.02220.47150.26180.114*
H14C0.05180.34750.30220.114*
C150.12062 (8)0.4301 (3)0.09044 (7)0.0550 (6)
H15A0.10810.45530.05910.066*
C160.19925 (8)0.4445 (3)0.07622 (8)0.0524 (6)
C170.24714 (8)0.5059 (3)0.09644 (8)0.0567 (6)
C180.28038 (9)0.5363 (3)0.07005 (10)0.0716 (7)
H18A0.31210.57770.08400.086*
C190.26641 (10)0.5051 (4)0.02291 (10)0.0794 (8)
H19A0.28860.52580.00480.095*
C200.21944 (9)0.4430 (4)0.00270 (9)0.0761 (8)
H20A0.21010.42260.02910.091*
C210.18616 (8)0.4108 (3)0.02871 (8)0.0632 (6)
H21A0.15490.36640.01460.076*
C220.26084 (8)0.5404 (4)0.14511 (10)0.0700 (7)
C230.24659 (7)0.9944 (3)0.04970 (7)0.0498 (5)
C240.23205 (7)0.9758 (3)0.00082 (7)0.0524 (6)
C250.26610 (7)0.9935 (3)0.02562 (7)0.0539 (6)
C260.31490 (7)1.0267 (3)0.00171 (7)0.0588 (6)
H26A0.33831.03690.01890.071*
C270.33121 (7)1.0459 (3)0.04689 (7)0.0554 (6)
C280.29620 (7)1.0291 (3)0.07106 (7)0.0535 (6)
H28A0.30571.04110.10320.064*
C290.25076 (8)0.9747 (3)0.07914 (7)0.0609 (6)
C300.29447 (8)1.0043 (4)0.10075 (8)0.0781 (8)
H30A0.31980.91650.08840.117*
H30B0.30741.12520.09360.117*
H30C0.28360.98980.13380.117*
C310.23030 (8)0.7842 (4)0.09238 (8)0.0809 (8)
H31A0.25490.69500.07900.121*
H31B0.22160.77210.12550.121*
H31C0.20150.76550.08090.121*
C320.21179 (8)1.1207 (4)0.10026 (7)0.0864 (8)
H32A0.18371.10740.08750.130*
H32B0.20171.10550.13330.130*
H32C0.22581.24000.09310.130*
C330.38584 (7)1.0851 (3)0.06904 (8)0.0656 (7)
C340.40101 (8)1.2618 (4)0.04893 (9)0.1017 (10)
H34A0.39571.24940.01600.153*
H34B0.43531.28570.06260.153*
H34C0.38151.36120.05560.153*
C350.39540 (8)1.1110 (4)0.12172 (8)0.0823 (8)
H35A0.37641.21250.12800.124*
H35B0.42991.13420.13470.124*
H35C0.38591.00250.13530.124*
C360.41687 (8)0.9228 (4)0.06066 (9)0.0991 (10)
H36A0.41180.90370.02790.149*
H36B0.40720.81540.07460.149*
H36C0.45120.94740.07420.149*
C370.21240 (7)0.9782 (3)0.07787 (7)0.0528 (6)
H37A0.22420.99310.10970.063*
C380.13442 (7)0.9239 (3)0.09128 (7)0.0498 (5)
C390.14876 (8)0.8607 (3)0.13675 (8)0.0606 (6)
H39A0.18170.83110.14960.073*
C400.08411 (8)0.9640 (3)0.07310 (8)0.0543 (6)
C410.05055 (8)0.9410 (3)0.09933 (9)0.0678 (7)
H41A0.01740.96680.08660.081*
C420.06576 (9)0.8799 (3)0.14438 (9)0.0725 (7)
H42A0.04310.86480.16220.087*
C430.11512 (9)0.8414 (3)0.16280 (8)0.0701 (7)
H43A0.12570.80170.19340.084*
C440.06939 (8)1.0420 (4)0.02734 (9)0.0669 (7)
C450.42247 (7)0.9779 (3)0.28519 (7)0.0497 (6)
C460.37210 (7)1.0054 (3)0.26459 (7)0.0524 (6)
H46A0.36211.02020.23260.063*
C470.33720 (7)1.0114 (3)0.28913 (7)0.0528 (6)
C480.35431 (7)0.9892 (3)0.33760 (7)0.0575 (6)
H48A0.33110.99260.35510.069*
C490.40353 (7)0.9625 (3)0.36098 (7)0.0535 (6)
C500.43758 (7)0.9546 (3)0.33395 (7)0.0524 (6)
C510.28202 (7)1.0428 (3)0.26768 (8)0.0640 (7)
C520.27148 (8)1.0677 (4)0.21492 (7)0.0810 (8)
H52A0.28100.95930.20130.121*
H52B0.29001.16980.20810.121*
H52C0.23691.08950.20240.121*
C530.26556 (8)1.2169 (4)0.28790 (9)0.0998 (10)
H53A0.27151.20470.32090.150*
H53B0.23091.23630.27460.150*
H53C0.28391.31910.28080.150*
C540.25289 (8)0.8771 (4)0.27695 (9)0.0947 (9)
H54A0.25910.85790.30980.142*
H54B0.26300.77120.26270.142*
H54C0.21830.89790.26410.142*
C550.41951 (8)0.9427 (3)0.41447 (7)0.0596 (6)
C560.37603 (8)0.9617 (4)0.43647 (7)0.0748 (7)
H56A0.35200.86920.42430.112*
H56B0.36131.08000.42940.112*
H56C0.38750.94780.46950.112*
C570.45652 (8)1.0928 (4)0.43532 (7)0.0792 (8)
H57A0.46631.07940.46840.119*
H57B0.44141.21010.42760.119*
H57C0.48501.08300.42300.119*
C580.44251 (8)0.7541 (4)0.42697 (8)0.0768 (7)
H58A0.41890.66160.41360.115*
H58B0.45180.74050.46010.115*
H58C0.47120.74190.41500.115*
C590.45650 (7)0.9795 (3)0.25691 (7)0.0524 (6)
H59A0.44421.00090.22530.063*
C600.53436 (7)0.9589 (3)0.24184 (7)0.0502 (6)
C610.58307 (8)1.0150 (3)0.25981 (8)0.0542 (6)
C620.61611 (8)1.0212 (3)0.23255 (9)0.0667 (7)
H62A0.64851.05780.24530.080*
C630.60124 (9)0.9730 (3)0.18625 (9)0.0738 (7)
H63A0.62330.97850.16750.089*
C640.55325 (9)0.9169 (3)0.16834 (8)0.0709 (7)
H64A0.54300.88430.13720.085*
C650.52018 (8)0.9078 (3)0.19529 (7)0.0606 (6)
H65A0.48810.86740.18250.073*
C660.59803 (8)1.0731 (4)0.30739 (9)0.0685 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0411 (9)0.1099 (14)0.0502 (10)0.0016 (9)0.0002 (8)0.0064 (9)
O20.0390 (9)0.1115 (14)0.0492 (10)0.0063 (9)0.0007 (8)0.0077 (9)
O30.0383 (9)0.1148 (14)0.0463 (10)0.0079 (9)0.0000 (8)0.0056 (9)
N10.0488 (11)0.0636 (12)0.0500 (12)0.0004 (9)0.0073 (9)0.0037 (9)
N20.0710 (15)0.136 (2)0.0851 (18)0.0008 (14)0.0003 (14)0.0288 (17)
N30.0455 (11)0.0634 (12)0.0461 (11)0.0004 (9)0.0093 (9)0.0026 (9)
N40.0746 (15)0.119 (2)0.0790 (17)0.0005 (14)0.0018 (13)0.0166 (15)
N50.0441 (10)0.0683 (13)0.0480 (11)0.0040 (9)0.0081 (9)0.0014 (9)
N60.0743 (15)0.140 (2)0.0859 (18)0.0056 (14)0.0030 (14)0.0344 (17)
C10.0422 (12)0.0613 (14)0.0443 (13)0.0019 (10)0.0016 (11)0.0056 (11)
C20.0391 (12)0.0692 (15)0.0487 (14)0.0021 (11)0.0033 (11)0.0002 (11)
C30.0437 (12)0.0664 (15)0.0480 (14)0.0015 (11)0.0018 (11)0.0001 (11)
C40.0457 (13)0.0789 (17)0.0505 (14)0.0025 (11)0.0061 (11)0.0011 (12)
C50.0391 (12)0.0694 (15)0.0523 (14)0.0005 (11)0.0007 (11)0.0026 (12)
C60.0464 (13)0.0689 (15)0.0465 (13)0.0017 (11)0.0039 (11)0.0021 (11)
C70.0402 (13)0.098 (2)0.0601 (16)0.0004 (13)0.0024 (12)0.0027 (14)
C80.0559 (16)0.176 (3)0.115 (3)0.031 (2)0.0095 (16)0.034 (2)
C90.0650 (18)0.191 (4)0.129 (3)0.056 (2)0.0181 (18)0.072 (3)
C100.0553 (15)0.134 (2)0.0692 (18)0.0051 (15)0.0158 (14)0.0109 (17)
C110.0547 (14)0.0782 (17)0.0439 (13)0.0018 (12)0.0029 (11)0.0064 (12)
C120.0742 (16)0.107 (2)0.0666 (17)0.0195 (16)0.0107 (14)0.0202 (15)
C130.0811 (17)0.111 (2)0.0473 (15)0.0183 (16)0.0004 (14)0.0039 (14)
C140.0752 (16)0.098 (2)0.0534 (15)0.0074 (14)0.0147 (13)0.0070 (14)
C150.0538 (14)0.0620 (15)0.0441 (14)0.0016 (11)0.0031 (12)0.0053 (11)
C160.0522 (14)0.0511 (14)0.0528 (15)0.0059 (11)0.0112 (12)0.0008 (11)
C170.0484 (14)0.0576 (15)0.0607 (16)0.0048 (11)0.0073 (13)0.0014 (12)
C180.0566 (15)0.0722 (17)0.087 (2)0.0037 (13)0.0189 (16)0.0056 (15)
C190.0749 (19)0.091 (2)0.081 (2)0.0123 (15)0.0348 (17)0.0212 (16)
C200.0789 (18)0.091 (2)0.0594 (17)0.0123 (16)0.0199 (16)0.0071 (14)
C210.0587 (15)0.0723 (16)0.0552 (15)0.0024 (12)0.0080 (13)0.0013 (12)
C220.0434 (14)0.0868 (19)0.0749 (19)0.0003 (12)0.0056 (14)0.0116 (16)
C230.0401 (12)0.0626 (15)0.0428 (13)0.0024 (10)0.0032 (11)0.0016 (11)
C240.0392 (12)0.0687 (16)0.0438 (14)0.0008 (11)0.0002 (11)0.0007 (11)
C250.0453 (13)0.0702 (16)0.0434 (13)0.0035 (11)0.0059 (11)0.0040 (11)
C260.0423 (13)0.0817 (17)0.0511 (15)0.0014 (11)0.0095 (11)0.0088 (12)
C270.0403 (12)0.0722 (16)0.0475 (14)0.0010 (11)0.0004 (11)0.0117 (11)
C280.0447 (13)0.0672 (15)0.0423 (13)0.0012 (11)0.0008 (11)0.0045 (11)
C290.0498 (13)0.0861 (18)0.0431 (14)0.0032 (13)0.0046 (11)0.0003 (12)
C300.0765 (17)0.106 (2)0.0522 (15)0.0026 (15)0.0177 (14)0.0063 (14)
C310.0751 (16)0.107 (2)0.0609 (16)0.0126 (16)0.0178 (13)0.0162 (15)
C320.0784 (17)0.124 (2)0.0473 (15)0.0266 (16)0.0018 (13)0.0121 (15)
C330.0394 (12)0.0897 (19)0.0598 (16)0.0020 (12)0.0023 (12)0.0162 (13)
C340.0578 (15)0.135 (3)0.099 (2)0.0259 (17)0.0057 (15)0.0427 (19)
C350.0522 (14)0.114 (2)0.0666 (17)0.0124 (14)0.0108 (13)0.0019 (15)
C360.0494 (15)0.149 (3)0.090 (2)0.0202 (17)0.0007 (15)0.0008 (19)
C370.0488 (13)0.0622 (15)0.0426 (13)0.0013 (11)0.0023 (11)0.0010 (11)
C380.0482 (13)0.0494 (13)0.0507 (14)0.0024 (10)0.0107 (11)0.0038 (10)
C390.0560 (14)0.0657 (16)0.0563 (15)0.0025 (12)0.0073 (12)0.0029 (12)
C400.0459 (13)0.0568 (14)0.0591 (15)0.0012 (11)0.0110 (12)0.0033 (11)
C410.0524 (14)0.0746 (17)0.0779 (19)0.0007 (12)0.0194 (14)0.0028 (14)
C420.0713 (17)0.0797 (19)0.0761 (19)0.0118 (14)0.0363 (15)0.0024 (15)
C430.0761 (17)0.0758 (18)0.0588 (16)0.0066 (14)0.0178 (14)0.0039 (13)
C440.0460 (14)0.0794 (19)0.0700 (19)0.0003 (12)0.0048 (14)0.0014 (15)
C450.0385 (12)0.0611 (14)0.0450 (14)0.0005 (10)0.0020 (11)0.0043 (10)
C460.0424 (12)0.0703 (16)0.0382 (12)0.0002 (11)0.0015 (11)0.0061 (11)
C470.0402 (12)0.0706 (16)0.0424 (13)0.0015 (11)0.0009 (11)0.0087 (11)
C480.0418 (13)0.0805 (17)0.0491 (14)0.0007 (11)0.0094 (11)0.0063 (12)
C490.0454 (13)0.0712 (16)0.0404 (13)0.0007 (11)0.0042 (11)0.0034 (11)
C500.0384 (12)0.0696 (16)0.0441 (14)0.0003 (11)0.0007 (11)0.0002 (11)
C510.0406 (13)0.0891 (18)0.0550 (15)0.0033 (12)0.0013 (11)0.0148 (13)
C520.0507 (14)0.118 (2)0.0624 (17)0.0142 (14)0.0087 (13)0.0008 (15)
C530.0545 (15)0.132 (3)0.098 (2)0.0263 (16)0.0081 (14)0.0435 (19)
C540.0516 (15)0.143 (3)0.083 (2)0.0193 (16)0.0044 (14)0.0018 (18)
C550.0537 (14)0.0783 (17)0.0427 (14)0.0005 (12)0.0044 (11)0.0006 (12)
C560.0736 (16)0.104 (2)0.0476 (15)0.0030 (15)0.0162 (13)0.0052 (13)
C570.0760 (16)0.110 (2)0.0425 (14)0.0182 (15)0.0029 (13)0.0039 (14)
C580.0681 (15)0.103 (2)0.0554 (15)0.0062 (15)0.0091 (13)0.0115 (14)
C590.0464 (13)0.0660 (15)0.0408 (13)0.0023 (11)0.0036 (11)0.0029 (10)
C600.0449 (13)0.0536 (14)0.0521 (15)0.0038 (10)0.0120 (12)0.0023 (11)
C610.0456 (13)0.0570 (14)0.0586 (15)0.0078 (11)0.0102 (12)0.0001 (11)
C620.0484 (14)0.0741 (17)0.0768 (19)0.0041 (12)0.0143 (14)0.0062 (14)
C630.0645 (17)0.093 (2)0.0718 (19)0.0136 (14)0.0317 (15)0.0139 (15)
C640.0679 (16)0.093 (2)0.0532 (16)0.0135 (14)0.0170 (14)0.0002 (13)
C650.0529 (14)0.0725 (16)0.0539 (15)0.0066 (12)0.0084 (12)0.0024 (12)
C660.0461 (14)0.0821 (19)0.0739 (19)0.0069 (12)0.0088 (14)0.0114 (15)
Geometric parameters (Å, º) top
C1—C61.402 (3)C30—H30C0.9600
C1—C21.417 (3)C31—H31A0.9600
C1—C151.429 (3)C31—H31B0.9600
N1—C151.282 (2)C31—H31C0.9600
N1—C161.413 (2)C32—H32A0.9600
O1—C21.359 (2)C32—H32B0.9600
O1—H1A0.87 (2)C32—H32C0.9600
C2—C31.386 (3)C33—C361.529 (3)
N2—C221.145 (3)C33—C341.531 (3)
O2—C241.361 (2)C33—C351.536 (3)
O2—H2A0.92 (3)C34—H34A0.9600
C3—C41.395 (2)C34—H34B0.9600
C3—C111.548 (3)C34—H34C0.9600
O3—C501.358 (2)C35—H35A0.9600
O3—H3A0.95 (2)C35—H35B0.9600
N3—C371.287 (2)C35—H35C0.9600
N3—C381.405 (2)C36—H36A0.9600
C4—C51.406 (3)C36—H36B0.9600
C4—H4A0.9300C36—H36C0.9600
N4—C441.138 (3)C37—H37A0.9300
C5—C61.354 (3)C38—C391.392 (3)
C5—C71.536 (3)C38—C401.406 (3)
N5—C591.277 (2)C39—C431.369 (3)
N5—C601.409 (2)C39—H39A0.9300
C6—H6A0.9300C40—C411.374 (3)
N6—C661.134 (3)C40—C441.440 (3)
C7—C91.501 (3)C41—C421.377 (3)
C7—C81.523 (4)C41—H41A0.9300
C7—C101.527 (3)C42—C431.381 (3)
C8—H8A0.9600C42—H42A0.9300
C8—H8B0.9600C43—H43A0.9300
C8—H8C0.9600C45—C461.403 (2)
C9—H9A0.9600C45—C501.417 (3)
C9—H9B0.9600C45—C591.421 (3)
C9—H9C0.9600C46—C471.359 (3)
C10—H10A0.9600C46—H46A0.9300
C10—H10B0.9600C47—C481.412 (3)
C10—H10C0.9600C47—C511.532 (3)
C11—C141.526 (3)C48—C491.392 (2)
C11—C121.532 (3)C48—H48A0.9300
C11—C131.538 (3)C49—C501.394 (3)
C12—H12A0.9600C49—C551.550 (3)
C12—H12B0.9600C51—C541.526 (3)
C12—H12C0.9600C51—C531.531 (3)
C13—H13A0.9600C51—C521.535 (3)
C13—H13B0.9600C52—H52A0.9600
C13—H13C0.9600C52—H52B0.9600
C14—H14A0.9600C52—H52C0.9600
C14—H14B0.9600C53—H53A0.9600
C14—H14C0.9600C53—H53B0.9600
C15—H15A0.9300C53—H53C0.9600
C16—C211.392 (3)C54—H54A0.9600
C16—C171.398 (3)C54—H54B0.9600
C17—C181.378 (3)C54—H54C0.9600
C17—C221.426 (3)C55—C561.526 (3)
C18—C191.379 (3)C55—C581.531 (3)
C18—H18A0.9300C55—C571.531 (3)
C19—C201.378 (3)C56—H56A0.9600
C19—H19A0.9300C56—H56B0.9600
C20—C211.373 (3)C56—H56C0.9600
C20—H20A0.9300C57—H57A0.9600
C21—H21A0.9300C57—H57B0.9600
C23—C281.397 (2)C57—H57C0.9600
C23—C241.416 (3)C58—H58A0.9600
C23—C371.427 (3)C58—H58B0.9600
C24—C251.386 (3)C58—H58C0.9600
C25—C261.393 (3)C59—H59A0.9300
C25—C291.550 (3)C60—C651.394 (3)
C26—C271.411 (3)C60—C611.395 (3)
C26—H26A0.9300C61—C621.376 (3)
C27—C281.359 (3)C61—C661.437 (3)
C27—C331.532 (3)C62—C631.383 (3)
C28—H28A0.9300C62—H62A0.9300
C29—C311.522 (3)C63—C641.377 (3)
C29—C301.533 (3)C63—H63A0.9300
C29—C321.544 (3)C64—C651.370 (3)
C30—H30A0.9600C64—H64A0.9300
C30—H30B0.9600C65—H65A0.9300
C6—C1—C2118.4 (2)H32B—C32—H32C109.5
C6—C1—C15119.16 (19)C36—C33—C34111.7 (2)
C2—C1—C15122.39 (18)C36—C33—C27109.3 (2)
C15—N1—C16120.80 (19)C34—C33—C27109.54 (18)
C2—O1—H1A111.2 (16)C36—C33—C35107.60 (19)
O1—C2—C3119.90 (19)C34—C33—C35107.5 (2)
O1—C2—C1119.2 (2)C27—C33—C35111.24 (19)
C3—C2—C1120.84 (18)C33—C34—H34A109.5
C24—O2—H2A112.0 (16)C33—C34—H34B109.5
C2—C3—C4117.13 (19)H34A—C34—H34B109.5
C2—C3—C11121.75 (18)C33—C34—H34C109.5
C4—C3—C11121.1 (2)H34A—C34—H34C109.5
C50—O3—H3A112.0 (14)H34B—C34—H34C109.5
C37—N3—C38121.36 (18)C33—C35—H35A109.5
C3—C4—C5123.9 (2)C33—C35—H35B109.5
C3—C4—H4A118.1H35A—C35—H35B109.5
C5—C4—H4A118.1C33—C35—H35C109.5
C6—C5—C4116.83 (18)H35A—C35—H35C109.5
C6—C5—C7123.6 (2)H35B—C35—H35C109.5
C4—C5—C7119.6 (2)C33—C36—H36A109.5
C59—N5—C60120.71 (18)C33—C36—H36B109.5
C5—C6—C1122.7 (2)H36A—C36—H36B109.5
C5—C6—H6A118.6C33—C36—H36C109.5
C1—C6—H6A118.6H36A—C36—H36C109.5
C9—C7—C8112.4 (2)H36B—C36—H36C109.5
C9—C7—C10107.8 (2)N3—C37—C23123.80 (19)
C8—C7—C10106.3 (2)N3—C37—H37A118.1
C9—C7—C5110.1 (2)C23—C37—H37A118.1
C8—C7—C5108.8 (2)C39—C38—N3124.82 (19)
C10—C7—C5111.5 (2)C39—C38—C40117.4 (2)
C7—C8—H8A109.5N3—C38—C40117.72 (19)
C7—C8—H8B109.5C43—C39—C38121.0 (2)
H8A—C8—H8B109.5C43—C39—H39A119.5
C7—C8—H8C109.5C38—C39—H39A119.5
H8A—C8—H8C109.5C41—C40—C38121.1 (2)
H8B—C8—H8C109.5C41—C40—C44120.9 (2)
C7—C9—H9A109.5C38—C40—C44117.9 (2)
C7—C9—H9B109.5C40—C41—C42120.4 (2)
H9A—C9—H9B109.5C40—C41—H41A119.8
C7—C9—H9C109.5C42—C41—H41A119.8
H9A—C9—H9C109.5C41—C42—C43119.2 (2)
H9B—C9—H9C109.5C41—C42—H42A120.4
C7—C10—H10A109.5C43—C42—H42A120.4
C7—C10—H10B109.5C39—C43—C42121.0 (2)
H10A—C10—H10B109.5C39—C43—H43A119.5
C7—C10—H10C109.5C42—C43—H43A119.5
H10A—C10—H10C109.5N4—C44—C40177.1 (3)
H10B—C10—H10C109.5C46—C45—C50118.3 (2)
C14—C11—C12107.80 (19)C46—C45—C59119.23 (19)
C14—C11—C13106.72 (19)C50—C45—C59122.45 (18)
C12—C11—C13110.55 (18)C47—C46—C45123.19 (19)
C14—C11—C3112.63 (17)C47—C46—H46A118.4
C12—C11—C3109.47 (19)C45—C46—H46A118.4
C13—C11—C3109.63 (18)C46—C47—C48116.18 (18)
C11—C12—H12A109.5C46—C47—C51124.39 (19)
C11—C12—H12B109.5C48—C47—C51119.4 (2)
H12A—C12—H12B109.5C49—C48—C47124.5 (2)
C11—C12—H12C109.5C49—C48—H48A117.7
H12A—C12—H12C109.5C47—C48—H48A117.7
H12B—C12—H12C109.5C48—C49—C50116.76 (19)
C11—C13—H13A109.5C48—C49—C55121.43 (19)
C11—C13—H13B109.5C50—C49—C55121.82 (18)
H13A—C13—H13B109.5O3—C50—C49119.65 (19)
C11—C13—H13C109.5O3—C50—C45119.30 (19)
H13A—C13—H13C109.5C49—C50—C45121.03 (19)
H13B—C13—H13C109.5C54—C51—C53111.4 (2)
C11—C14—H14A109.5C54—C51—C47109.5 (2)
C11—C14—H14B109.5C53—C51—C47109.39 (18)
H14A—C14—H14B109.5C54—C51—C52107.80 (19)
C11—C14—H14C109.5C53—C51—C52107.7 (2)
H14A—C14—H14C109.5C47—C51—C52111.05 (19)
H14B—C14—H14C109.5C51—C52—H52A109.5
N1—C15—C1124.0 (2)C51—C52—H52B109.5
N1—C15—H15A118.0H52A—C52—H52B109.5
C1—C15—H15A118.0C51—C52—H52C109.5
C21—C16—C17118.3 (2)H52A—C52—H52C109.5
C21—C16—N1124.3 (2)H52B—C52—H52C109.5
C17—C16—N1117.3 (2)C51—C53—H53A109.5
C18—C17—C16121.1 (2)C51—C53—H53B109.5
C18—C17—C22120.3 (2)H53A—C53—H53B109.5
C16—C17—C22118.6 (2)C51—C53—H53C109.5
C17—C18—C19119.7 (2)H53A—C53—H53C109.5
C17—C18—H18A120.2H53B—C53—H53C109.5
C19—C18—H18A120.2C51—C54—H54A109.5
C20—C19—C18119.7 (2)C51—C54—H54B109.5
C20—C19—H19A120.2H54A—C54—H54B109.5
C18—C19—H19A120.2C51—C54—H54C109.5
C21—C20—C19121.2 (2)H54A—C54—H54C109.5
C21—C20—H20A119.4H54B—C54—H54C109.5
C19—C20—H20A119.4C56—C55—C58108.01 (19)
C20—C21—C16120.0 (2)C56—C55—C57106.92 (19)
C20—C21—H21A120.0C58—C55—C57110.48 (19)
C16—C21—H21A120.0C56—C55—C49112.19 (17)
N2—C22—C17179.1 (3)C58—C55—C49109.25 (18)
C28—C23—C24118.8 (2)C57—C55—C49109.96 (18)
C28—C23—C37118.89 (19)C55—C56—H56A109.5
C24—C23—C37122.30 (18)C55—C56—H56B109.5
O2—C24—C25119.71 (19)H56A—C56—H56B109.5
O2—C24—C23119.35 (19)C55—C56—H56C109.5
C25—C24—C23120.92 (18)H56A—C56—H56C109.5
C24—C25—C26116.80 (19)H56B—C56—H56C109.5
C24—C25—C29121.59 (18)C55—C57—H57A109.5
C26—C25—C29121.6 (2)C55—C57—H57B109.5
C25—C26—C27124.4 (2)H57A—C57—H57B109.5
C25—C26—H26A117.8C55—C57—H57C109.5
C27—C26—H26A117.8H57A—C57—H57C109.5
C28—C27—C26116.37 (18)H57B—C57—H57C109.5
C28—C27—C33124.2 (2)C55—C58—H58A109.5
C26—C27—C33119.4 (2)C55—C58—H58B109.5
C27—C28—C23122.7 (2)H58A—C58—H58B109.5
C27—C28—H28A118.6C55—C58—H58C109.5
C23—C28—H28A118.6H58A—C58—H58C109.5
C31—C29—C30107.98 (19)H58B—C58—H58C109.5
C31—C29—C32110.41 (19)N5—C59—C45124.14 (19)
C30—C29—C32106.64 (19)N5—C59—H59A117.9
C31—C29—C25109.70 (19)C45—C59—H59A117.9
C30—C29—C25112.03 (17)C65—C60—C61117.9 (2)
C32—C29—C25110.02 (19)C65—C60—N5124.12 (19)
C29—C30—H30A109.5C61—C60—N5118.0 (2)
C29—C30—H30B109.5C62—C61—C60121.3 (2)
H30A—C30—H30B109.5C62—C61—C66120.0 (2)
C29—C30—H30C109.5C60—C61—C66118.7 (2)
H30A—C30—H30C109.5C61—C62—C63120.1 (2)
H30B—C30—H30C109.5C61—C62—H62A119.9
C29—C31—H31A109.5C63—C62—H62A119.9
C29—C31—H31B109.5C64—C63—C62118.9 (2)
H31A—C31—H31B109.5C64—C63—H63A120.6
C29—C31—H31C109.5C62—C63—H63A120.6
H31A—C31—H31C109.5C65—C64—C63121.5 (2)
H31B—C31—H31C109.5C65—C64—H64A119.2
C29—C32—H32A109.5C63—C64—H64A119.2
C29—C32—H32B109.5C64—C65—C60120.3 (2)
H32A—C32—H32B109.5C64—C65—H65A119.9
C29—C32—H32C109.5C60—C65—H65A119.9
H32A—C32—H32C109.5N6—C66—C61179.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···N50.95 (2)1.81 (2)2.622 (2)143 (2)
O2—H2A···N30.92 (3)1.82 (3)2.615 (2)143 (2)
O1—H1A···N10.87 (2)1.86 (2)2.623 (2)145 (2)

Experimental details

Crystal data
Chemical formulaC22H26N2O
Mr334.45
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)27.9710 (4), 7.32780 (11), 29.7840 (4)
β (°) 104.5330 (2)
V3)5909.37 (15)
Z12
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Bruker, 2000)
Tmin, Tmax0.948, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
30875, 11513, 4685
Rint0.130
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.173, 0.81
No. of reflections11513
No. of parameters689
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.31, 0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···N50.95 (2)1.81 (2)2.622 (2)143 (2)
O2—H2A···N30.92 (3)1.82 (3)2.615 (2)143 (2)
O1—H1A···N10.87 (2)1.86 (2)2.623 (2)145 (2)
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170–2171.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationDao, V.-T., Gaspard, C., Mayer, M., Werner, G. H., Nguyen, S. N. & Michelot, R. J. (2000). Eur. J. Med. Chem. 35, 805–813.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSriram, D., Yogeeswari, P., Myneedu, N. S. & Saraswat, V. (2006). Bioorg. Med. Chem. Lett. 16, 2127–2129.  Web of Science CrossRef PubMed CAS Google Scholar
First citationWeber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159–1162.  Web of Science CSD CrossRef CAS Google Scholar

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