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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1,1′-[o-Phenyl­enebis(nitrilo­methyl­­idyne)]di-2-naphthol ethanol hemisolvate

aDepartment of Chemistry, Shangqiu Normal University, Shangqiu, Henan Province 476000, People's Republic of China, bDepartment of Chemistry, Weifang Medical University, Weifang, Shandong Province 261053, People's Republic of China, cDepartment of Chemistry, Liaocheng University, Liaocheng 252059, People's Republic of China, and dShandong Donge Experimental High School, Donge, Shandong Province 252200, People's Republic of China
*Correspondence e-mail: hxqqxh2008@163.com

(Received 9 June 2008; accepted 13 July 2008; online 19 July 2008)

The asymmetric unit of the title compound, C28H20N2O2·0.5C2H5OH, contains two independent mol­ecules of 1,1′-[o-phenyl­enebis(nitrilo­methyl­idyne)]di-2-naphthol, denoted A and B, and one ethanol solvent mol­ecule. The hydr­oxy groups are involved in intra­molecular O—H⋯N hydrogen bonds influencing the mol­ecular conformations, which are slightly different in mol­ecules A and B, where the two bicyclic systems form dihedral angles of 51.93 (9) and 58.52 (9)°, respectively. In the crystal structure, a number of short inter­molecular C⋯C contacts with distances of less than 3.5 Å suggest the existence of ππ inter­actions, which contribute to the stability of the crystal packing.

Related literature

For related crystal structures, see: Zhang et al. (1990[Zhang, W., Loebach, J. L., Wilson, S. R. & Jacobsen, E. N. (1990). J. Am. Chem. Soc. 112, 2801-2804.]); Lo et al. (2006[Lo, W.-K., Wong, W.-K., Wong, W.-Y., Guo, J. P., Yeung, K.-T., Cheng, Y.-K., Yang, X. P. & Jones, R. A. (2006). Inorg. Chem. 45, 9315-9325.]); Eltayeb et al. (2007[Eltayeb, N. E., Teoh, S. G., Teh, J. B.-J., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, o117-o119.]).

[Scheme 1]

Experimental

Crystal data
  • C28H20N2O2·0.5C2H6O

  • Mr = 439.50

  • Orthorhombic, P n a 21

  • a = 19.956 (2) Å

  • b = 12.4742 (13) Å

  • c = 18.189 (2) Å

  • V = 4527.9 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 (2) K

  • 0.20 × 0.18 × 0.07 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.984, Tmax = 0.994

  • 21755 measured reflections

  • 4002 independent reflections

  • 1545 reflections with I > 2σ(I)

  • Rint = 0.176

Refinement
  • R[F2 > 2σ(F2)] = 0.094

  • wR(F2) = 0.121

  • S = 1.05

  • 4002 reflections

  • 605 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Selected interatomic distances (Å)

C8⋯C35 3.485 (16)
C12⋯C34 3.387 (16)
C15⋯C46 3.473 (15)
C1⋯C54i 3.462 (17)
C7⋯C52i 3.481 (15)
C9⋯C47i 3.402 (16)
C13⋯C49i 3.475 (16)
C19⋯C37ii 3.418 (15)
C26⋯C29ii 3.308 (17)
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H5⋯O3 0.82 1.99 2.790 (11) 166
O4—H4⋯N4 0.82 1.87 2.594 (11) 147
O3—H3⋯N3 0.82 1.81 2.550 (10) 149
O2—H2⋯N2 0.82 1.85 2.578 (10) 148
O1—H1⋯N1 0.82 1.79 2.535 (9) 149

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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: SHELXTL.

Supporting information


Comment top

Salen-type ligands are amongst the oldest ligands in coordination chemistry and have received considerable interest since Jacobsen and Katsuki first reported their significant success using chiral manganese (III) salen Schiff base catalysts in the asymmetric epoxidation of unfunctionalized olefins (Zhang et al., 1990). In this paper, we report the crystal structure of the title compound, (I), obtained by the reaction of o-phenylenediamine and 2-hydroxy-1- naphthaldehyde.

All bond lengths and angles in (I) have normal values (Eltayeb et al., 2007). The asymmetric unit of (I) contain two independent molecules (A and B) and one ethanol solvent molecule (Fig. 1). In A, the dihedral angles C12-C17/C1-C10, C12-C17/C19-C28 and C1-C10/C19-C28 are 4.71 (9), 51.28 (9) and 55.97 (7) °, respectively. In B, the dihedral angles C40-C45/C29-C38, C40-C45/C48-C56 and C29-C38/C48-C56 are 1.80 (9), 58.29 (9) and 59.84 (6) °, respectively. The hydroxyl groups are involved in intramolecular O—H···N hydrogen bonds (Table 2) influencing the molecular conformations.

In the crystal, a number of short intermolecular C···C contacts with the distances less than 3.5 Å (Table 1) suggest an existence of π-π interactions, which contribute to the crystal packing stability.

Related literature top

For related crystal structures, see: Zhang et al. (1990); Lo et al. (2006); Eltayeb et al. (2007).

Experimental top

To a solution of o-phenylenediamine (3 mmol) in ethanol (30 ml) was added 2-hydroxy-1-naphthaldehyde (6 mmol). The mixture was refluxed with stirring for 20 min. An orange precipitate was then obtained. Red crystals suitable for X-ray diffraction analysis formed after several weeks on slow evaporation of a ethanol solution at room temperature. Elemental analysis: calculated for C58H46N4O5: C 79.25, H 5.27, N 6.37%; found: C 79.28, H 5.22, N 6.45%.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.98 Å and Uiso(H) = 1.2-1.5 Ueq(C). The H atoms of hydroxyl were placed in idealized positions , O—H 0.82%/A, the Uiso(H) values were set at 1.5 Ueq(O). In the absence of any significant anomalous scatterers in the compound, the 3833 Friedel pairs were merged before the final refinement.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The content of asymmetric unit of the title compound showing the atomic numbering scheme and 30% probability displacement ellipsoids. Hydrogen atoms and solvent molecule omitted for clarity.
1,1'-[o-Phenylenebis(nitrilomethylidyne)]di-2-naphthol ethanol hemisolvate top
Crystal data top
C28H20N2O2·0.5(C2H6O)Dx = 1.289 Mg m3
Mr = 439.50Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 1646 reflections
a = 19.956 (2) Åθ = 2.9–28.1°
b = 12.4742 (13) ŵ = 0.08 mm1
c = 18.189 (2) ÅT = 298 K
V = 4527.9 (8) Å3Block, yellow
Z = 80.20 × 0.18 × 0.07 mm
F(000) = 1848
Data collection top
Bruker SMART CCD area-detector
diffractometer
4002 independent reflections
Radiation source: fine-focus sealed tube1545 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.176
ϕ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1923
Tmin = 0.984, Tmax = 0.994k = 1414
21755 measured reflectionsl = 2121
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)] = 0.094Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.026P)2]
where P = (Fo2 + 2Fc2)/3
4002 reflections(Δ/σ)max = 0.001
605 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.16 e Å3
Crystal data top
C28H20N2O2·0.5(C2H6O)V = 4527.9 (8) Å3
Mr = 439.50Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 19.956 (2) ŵ = 0.08 mm1
b = 12.4742 (13) ÅT = 298 K
c = 18.189 (2) Å0.20 × 0.18 × 0.07 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4002 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1545 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.994Rint = 0.176
21755 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0941 restraint
wR(F2) = 0.121H-atom parameters constrained
S = 1.06Δρmax = 0.15 e Å3
4002 reflectionsΔρmin = 0.16 e Å3
605 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
N10.4622 (4)0.4463 (5)0.2203 (4)0.061 (2)
N20.5628 (4)0.3113 (6)0.1967 (4)0.065 (2)
N30.2294 (4)0.5681 (6)0.1085 (4)0.061 (2)
N40.1288 (4)0.7009 (6)0.1347 (5)0.069 (2)
O10.5069 (4)0.5421 (5)0.1076 (4)0.087 (2)
H10.50210.49460.13830.130*
O20.6557 (3)0.4250 (5)0.1367 (4)0.088 (2)
H20.62660.40910.16660.132*
O30.1832 (4)0.4657 (5)0.2186 (4)0.090 (2)
H30.18630.51300.18760.136*
O40.0335 (4)0.5789 (5)0.1839 (4)0.090 (3)
H40.06400.59760.15650.136*
O50.1992 (5)0.5525 (9)0.3589 (5)0.175 (5)
H50.19730.51750.32080.263*
C10.4667 (5)0.3606 (7)0.2677 (5)0.058 (3)
C20.5175 (6)0.2856 (7)0.2548 (5)0.065 (3)
C30.5266 (6)0.1963 (8)0.2979 (6)0.081 (3)
H3A0.56220.14990.28900.097*
C40.4820 (6)0.1766 (8)0.3547 (6)0.083 (3)
H4A0.48620.11450.38260.100*
C50.4317 (6)0.2479 (8)0.3701 (6)0.085 (4)
H5A0.40330.23570.40980.102*
C60.4232 (6)0.3379 (8)0.3269 (5)0.075 (3)
H60.38810.38450.33700.090*
C70.4192 (5)0.5246 (7)0.2259 (5)0.058 (3)
H70.38920.52340.26500.070*
C80.4156 (6)0.6088 (8)0.1773 (6)0.061 (3)
C90.4628 (6)0.6155 (8)0.1181 (7)0.069 (3)
C100.4633 (6)0.7026 (9)0.0693 (6)0.081 (3)
H100.49290.70360.02990.097*
C110.4208 (7)0.7840 (9)0.0800 (7)0.085 (4)
H110.42350.84360.04930.102*
C120.3710 (6)0.7826 (8)0.1374 (6)0.070 (3)
C130.3675 (5)0.6957 (8)0.1864 (6)0.059 (3)
C140.3169 (6)0.6970 (9)0.2400 (5)0.067 (3)
H140.31260.63950.27230.081*
C150.2741 (6)0.7811 (9)0.2454 (6)0.082 (4)
H150.24050.77910.28090.099*
C160.2785 (6)0.8696 (9)0.2000 (7)0.087 (4)
H160.24970.92770.20560.104*
C170.3271 (6)0.8687 (9)0.1464 (6)0.082 (4)
H170.33080.92740.11510.098*
C180.5801 (5)0.2358 (8)0.1518 (5)0.057 (3)
H180.56140.16800.15780.069*
C190.6269 (5)0.2526 (7)0.0933 (5)0.053 (3)
C200.6634 (6)0.3443 (8)0.0881 (6)0.070 (3)
C210.7127 (6)0.3604 (10)0.0342 (7)0.090 (4)
H210.73690.42420.03290.108*
C220.7249 (7)0.2819 (12)0.0164 (7)0.097 (4)
H220.75820.29170.05160.116*
C230.6875 (6)0.1859 (11)0.0156 (6)0.079 (3)
C240.6383 (6)0.1729 (8)0.0383 (6)0.064 (3)
C250.6016 (6)0.0770 (9)0.0364 (5)0.077 (3)
H250.56870.06500.07170.093*
C260.6131 (7)0.0004 (9)0.0165 (7)0.091 (4)
H260.58710.06150.01670.109*
C270.6626 (8)0.0126 (11)0.0696 (7)0.112 (5)
H270.67010.03990.10500.134*
C280.6992 (8)0.1034 (12)0.0680 (6)0.104 (5)
H280.73330.11240.10220.125*
C290.2245 (6)0.6585 (8)0.0626 (5)0.061 (3)
C300.1732 (6)0.7312 (8)0.0783 (6)0.061 (3)
C310.1655 (6)0.8246 (8)0.0391 (5)0.073 (3)
H310.13120.87230.05030.087*
C320.2102 (7)0.8460 (9)0.0176 (7)0.092 (4)
H320.20590.90910.04450.111*
C330.2607 (8)0.7748 (11)0.0346 (6)0.099 (5)
H330.28940.78960.07350.119*
C340.2692 (6)0.6825 (10)0.0052 (6)0.084 (4)
H340.30430.63610.00570.101*
C350.2738 (6)0.4901 (9)0.1006 (5)0.070 (3)
H350.30480.49400.06250.085*
C360.2755 (5)0.4010 (10)0.1486 (6)0.065 (3)
C370.2286 (6)0.3932 (9)0.2067 (6)0.070 (3)
C380.2295 (7)0.3021 (11)0.2539 (6)0.095 (4)
H380.19840.29630.29180.114*
C390.2755 (7)0.2246 (10)0.2437 (7)0.096 (4)
H390.27600.16690.27600.115*
C400.3226 (6)0.2265 (11)0.1868 (7)0.082 (3)
C410.3239 (6)0.3154 (10)0.1385 (6)0.070 (3)
C420.3731 (7)0.3146 (9)0.0840 (7)0.090 (4)
H420.37550.37200.05150.107*
C430.4186 (6)0.2309 (11)0.0766 (9)0.108 (5)
H430.45130.23280.04030.130*
C440.4144 (7)0.1455 (12)0.1239 (9)0.110 (5)
H440.44400.08840.11880.132*
C450.3684 (7)0.1434 (11)0.1771 (8)0.100 (5)
H450.36680.08480.20870.120*
C460.1101 (5)0.7724 (7)0.1818 (5)0.062 (3)
H460.12840.84090.17900.074*
C470.0611 (6)0.7490 (8)0.2394 (5)0.066 (3)
C480.0233 (6)0.6535 (10)0.2340 (6)0.072 (3)
C490.0279 (6)0.6367 (9)0.2871 (8)0.089 (4)
H490.05440.57550.28420.107*
C500.0385 (7)0.7058 (12)0.3396 (6)0.104 (5)
H500.07340.69080.37180.124*
C510.0030 (8)0.7987 (10)0.3522 (7)0.095 (4)
C520.0501 (6)0.8240 (9)0.2981 (6)0.076 (3)
C530.0881 (6)0.9171 (10)0.3089 (6)0.084 (4)
H530.12160.93490.27550.101*
C540.0765 (8)0.9826 (9)0.3685 (8)0.132 (6)
H540.10311.04290.37570.159*
C550.0237 (10)0.9590 (13)0.4198 (7)0.134 (7)
H550.01441.00410.45920.161*
C560.0111 (9)0.8695 (13)0.4085 (8)0.124 (6)
H560.04450.85380.44250.148*
C570.1328 (10)0.5731 (16)0.3850 (11)0.188 (8)
H57A0.12990.64840.39770.226*
H57B0.10200.56080.34460.226*
C580.1125 (10)0.5189 (14)0.4398 (11)0.220 (9)
H58A0.11980.44400.43070.329*
H58B0.06560.53170.44730.329*
H58C0.13690.54020.48300.329*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.086 (7)0.021 (4)0.074 (5)0.002 (4)0.003 (5)0.004 (4)
N20.056 (6)0.066 (5)0.073 (6)0.002 (5)0.004 (5)0.008 (5)
N30.061 (6)0.059 (5)0.062 (5)0.004 (5)0.003 (5)0.008 (5)
N40.069 (7)0.068 (5)0.070 (6)0.007 (5)0.004 (6)0.000 (5)
O10.095 (6)0.086 (5)0.079 (5)0.006 (5)0.019 (5)0.007 (4)
O20.068 (6)0.073 (4)0.123 (6)0.013 (4)0.019 (5)0.005 (5)
O30.087 (6)0.113 (5)0.070 (5)0.013 (5)0.007 (5)0.010 (4)
O40.095 (7)0.083 (5)0.093 (5)0.020 (5)0.004 (5)0.003 (5)
O50.127 (9)0.277 (13)0.122 (8)0.038 (10)0.012 (8)0.059 (8)
C10.059 (8)0.043 (6)0.073 (7)0.003 (6)0.007 (6)0.020 (6)
C20.079 (9)0.050 (6)0.065 (7)0.017 (6)0.007 (7)0.007 (6)
C30.072 (9)0.075 (8)0.096 (9)0.012 (7)0.012 (8)0.010 (7)
C40.081 (9)0.088 (8)0.081 (8)0.011 (7)0.016 (7)0.030 (7)
C50.093 (10)0.093 (9)0.070 (8)0.011 (7)0.036 (7)0.013 (7)
C60.085 (9)0.078 (8)0.063 (7)0.011 (7)0.013 (7)0.002 (6)
C70.076 (8)0.041 (5)0.058 (6)0.012 (6)0.000 (6)0.004 (5)
C80.066 (9)0.057 (7)0.060 (7)0.013 (6)0.002 (7)0.009 (6)
C90.074 (10)0.057 (7)0.077 (8)0.003 (7)0.016 (8)0.014 (7)
C100.083 (11)0.081 (8)0.077 (8)0.000 (8)0.004 (7)0.002 (7)
C110.094 (11)0.086 (9)0.075 (9)0.015 (8)0.007 (8)0.013 (7)
C120.064 (9)0.073 (7)0.072 (8)0.001 (7)0.022 (7)0.011 (7)
C130.065 (8)0.057 (6)0.054 (6)0.007 (6)0.022 (7)0.004 (6)
C140.061 (8)0.076 (7)0.066 (7)0.001 (7)0.006 (7)0.015 (6)
C150.068 (10)0.084 (8)0.094 (9)0.001 (8)0.013 (7)0.025 (8)
C160.080 (10)0.070 (8)0.110 (10)0.011 (7)0.021 (9)0.020 (8)
C170.079 (10)0.083 (8)0.082 (9)0.001 (8)0.014 (8)0.007 (7)
C180.047 (7)0.062 (6)0.062 (7)0.007 (6)0.002 (6)0.021 (6)
C190.062 (8)0.032 (5)0.066 (7)0.014 (5)0.005 (6)0.007 (5)
C200.074 (9)0.044 (6)0.091 (8)0.009 (6)0.008 (7)0.006 (6)
C210.075 (10)0.088 (9)0.107 (10)0.007 (8)0.024 (8)0.031 (8)
C220.090 (11)0.109 (11)0.091 (10)0.010 (9)0.019 (9)0.037 (8)
C230.075 (9)0.109 (10)0.053 (7)0.023 (8)0.016 (7)0.028 (7)
C240.064 (8)0.050 (6)0.077 (8)0.008 (6)0.009 (7)0.021 (6)
C250.098 (10)0.083 (8)0.050 (6)0.041 (7)0.010 (6)0.004 (6)
C260.104 (11)0.094 (9)0.074 (8)0.008 (8)0.025 (8)0.000 (8)
C270.153 (17)0.113 (11)0.069 (9)0.035 (11)0.011 (10)0.013 (9)
C280.129 (14)0.130 (11)0.052 (7)0.044 (11)0.015 (8)0.001 (9)
C290.076 (9)0.058 (6)0.050 (6)0.009 (6)0.011 (6)0.013 (6)
C300.070 (9)0.058 (7)0.053 (7)0.009 (6)0.004 (6)0.009 (6)
C310.091 (10)0.074 (7)0.053 (6)0.015 (6)0.002 (7)0.009 (6)
C320.125 (12)0.080 (9)0.072 (8)0.024 (9)0.020 (9)0.005 (7)
C330.135 (15)0.099 (10)0.064 (8)0.042 (10)0.003 (8)0.001 (8)
C340.083 (10)0.105 (10)0.065 (7)0.024 (8)0.021 (7)0.012 (7)
C350.070 (9)0.085 (7)0.057 (7)0.018 (7)0.004 (6)0.021 (6)
C360.030 (7)0.098 (9)0.066 (8)0.002 (7)0.003 (6)0.013 (7)
C370.046 (8)0.098 (9)0.067 (8)0.006 (7)0.015 (7)0.005 (7)
C380.096 (12)0.126 (10)0.062 (8)0.000 (9)0.013 (8)0.029 (8)
C390.087 (11)0.108 (10)0.091 (10)0.000 (9)0.020 (9)0.019 (8)
C400.067 (10)0.093 (9)0.085 (9)0.000 (8)0.007 (8)0.011 (8)
C410.045 (8)0.095 (9)0.069 (8)0.009 (7)0.002 (7)0.012 (7)
C420.085 (10)0.079 (8)0.105 (10)0.007 (8)0.005 (9)0.013 (7)
C430.068 (11)0.093 (10)0.163 (13)0.009 (9)0.000 (9)0.017 (10)
C440.072 (12)0.096 (11)0.161 (15)0.010 (9)0.014 (11)0.032 (11)
C450.081 (12)0.089 (9)0.130 (14)0.009 (9)0.014 (10)0.006 (9)
C460.061 (8)0.062 (6)0.063 (7)0.005 (6)0.010 (6)0.012 (6)
C470.061 (8)0.076 (7)0.060 (7)0.005 (7)0.009 (6)0.012 (6)
C480.060 (9)0.093 (9)0.063 (7)0.002 (8)0.002 (7)0.031 (7)
C490.064 (9)0.098 (9)0.105 (10)0.006 (7)0.008 (9)0.028 (8)
C500.118 (13)0.123 (12)0.070 (9)0.050 (11)0.026 (9)0.015 (9)
C510.138 (14)0.078 (10)0.070 (9)0.051 (9)0.003 (10)0.004 (8)
C520.087 (10)0.084 (9)0.056 (7)0.026 (8)0.000 (7)0.013 (7)
C530.098 (11)0.085 (8)0.069 (8)0.028 (8)0.012 (7)0.007 (7)
C540.198 (18)0.112 (11)0.087 (9)0.065 (11)0.040 (11)0.025 (9)
C550.21 (2)0.130 (13)0.060 (9)0.080 (14)0.012 (11)0.013 (10)
C560.176 (18)0.116 (11)0.078 (10)0.077 (12)0.017 (10)0.023 (10)
C570.17 (2)0.26 (2)0.134 (17)0.003 (19)0.054 (16)0.041 (15)
C580.24 (2)0.26 (2)0.157 (17)0.066 (17)0.024 (17)0.073 (14)
Geometric parameters (Å, º) top
N1—C71.304 (9)C25—H250.9300
N1—C11.376 (10)C26—C271.389 (16)
N2—C181.294 (10)C26—H260.9300
N2—C21.426 (10)C27—C281.349 (15)
N3—C351.324 (11)C27—H270.9300
N3—C291.406 (10)C28—H280.9300
N4—C461.292 (10)C29—C301.398 (12)
N4—C301.408 (11)C29—C341.405 (13)
O1—C91.284 (11)C30—C311.374 (12)
O1—H10.8200C31—C321.389 (14)
O2—C201.348 (10)C31—H310.9300
O2—H20.8200C32—C331.378 (14)
O3—C371.299 (10)C32—H320.9300
O3—H30.8200C33—C341.370 (14)
O4—C481.319 (12)C33—H330.9300
O4—H40.8200C34—H340.9300
O5—C571.43 (2)C35—C361.414 (13)
O5—H50.8200C35—H350.9300
C1—C21.400 (12)C36—C371.415 (13)
C1—C61.411 (12)C36—C411.452 (14)
C2—C31.374 (12)C37—C381.424 (12)
C3—C41.387 (13)C38—C391.347 (14)
C3—H3A0.9300C38—H380.9300
C4—C51.369 (12)C39—C401.397 (14)
C4—H4A0.9300C39—H390.9300
C5—C61.381 (12)C40—C451.392 (15)
C5—H5A0.9300C40—C411.415 (14)
C6—H60.9300C41—C421.394 (13)
C7—C81.374 (12)C42—C431.390 (14)
C7—H70.9300C42—H420.9300
C8—C91.434 (14)C43—C441.371 (16)
C8—C131.456 (13)C43—H430.9300
C9—C101.402 (13)C44—C451.335 (16)
C10—C111.337 (14)C44—H440.9300
C10—H100.9300C45—H450.9300
C11—C121.442 (14)C46—C471.463 (12)
C11—H110.9300C46—H460.9300
C12—C171.396 (13)C47—C481.413 (13)
C12—C131.405 (12)C47—C521.436 (13)
C13—C141.405 (12)C48—C491.421 (14)
C14—C151.357 (12)C49—C501.304 (13)
C14—H140.9300C49—H490.9300
C15—C161.381 (12)C50—C511.377 (16)
C15—H150.9300C50—H500.9300
C16—C171.377 (14)C51—C561.361 (14)
C16—H160.9300C51—C521.480 (16)
C17—H170.9300C52—C531.401 (14)
C18—C191.432 (12)C53—C541.377 (15)
C18—H180.9300C53—H530.9300
C19—C201.359 (12)C54—C551.437 (18)
C19—C241.428 (12)C54—H540.9300
C20—C211.404 (13)C55—C561.332 (19)
C21—C221.366 (14)C55—H550.9300
C21—H210.9300C56—H560.9300
C22—C231.411 (14)C57—C581.271 (18)
C22—H220.9300C57—H57A0.9700
C23—C241.398 (13)C57—H57B0.9700
C23—C281.421 (15)C58—H58A0.9600
C24—C251.403 (13)C58—H58B0.9600
C25—C261.377 (13)C58—H58C0.9600
C8···C353.485 (16)C9···C47i3.402 (16)
C12···C343.387 (16)C13···C49i3.475 (16)
C15···C463.473 (15)C19···C37ii3.418 (15)
C1···C54i3.462 (17)C26···C29ii3.308 (17)
C7···C52i3.481 (15)
C7—N1—C1125.2 (9)C34—C29—N3124.6 (11)
C18—N2—C2118.2 (8)C31—C30—C29121.7 (11)
C35—N3—C29124.9 (10)C31—C30—N4122.4 (11)
C46—N4—C30118.6 (9)C29—C30—N4115.8 (9)
C9—O1—H1109.5C30—C31—C32118.5 (11)
C20—O2—H2109.5C30—C31—H31120.8
C37—O3—H3109.5C32—C31—H31120.8
C48—O4—H4109.5C33—C32—C31120.7 (12)
C57—O5—H5109.5C33—C32—H32119.6
N1—C1—C2117.5 (10)C31—C32—H32119.6
N1—C1—C6126.4 (10)C34—C33—C32121.0 (13)
C2—C1—C6116.1 (9)C34—C33—H33119.5
C3—C2—C1122.8 (11)C32—C33—H33119.5
C3—C2—N2121.4 (11)C33—C34—C29119.5 (12)
C1—C2—N2115.6 (9)C33—C34—H34120.3
C2—C3—C4118.9 (11)C29—C34—H34120.3
C2—C3—H3A120.5N3—C35—C36121.8 (10)
C4—C3—H3A120.5N3—C35—H35119.1
C5—C4—C3120.6 (10)C36—C35—H35119.1
C5—C4—H4A119.7C35—C36—C37120.0 (11)
C3—C4—H4A119.7C35—C36—C41121.0 (11)
C4—C5—C6120.1 (10)C37—C36—C41118.9 (11)
C4—C5—H5A120.0O3—C37—C36122.6 (11)
C6—C5—H5A120.0O3—C37—C38117.6 (12)
C5—C6—C1121.5 (10)C36—C37—C38119.8 (12)
C5—C6—H6119.3C39—C38—C37119.9 (13)
C1—C6—H6119.3C39—C38—H38120.0
N1—C7—C8123.9 (10)C37—C38—H38120.0
N1—C7—H7118.0C38—C39—C40123.3 (13)
C8—C7—H7118.0C38—C39—H39118.4
C7—C8—C9119.5 (11)C40—C39—H39118.4
C7—C8—C13122.1 (11)C45—C40—C39121.4 (15)
C9—C8—C13118.3 (10)C45—C40—C41119.5 (13)
O1—C9—C10116.9 (12)C39—C40—C41119.0 (13)
O1—C9—C8121.4 (11)C42—C41—C40116.6 (12)
C10—C9—C8121.7 (11)C42—C41—C36124.3 (12)
C11—C10—C9119.5 (12)C40—C41—C36119.1 (12)
C11—C10—H10120.3C43—C42—C41122.3 (13)
C9—C10—H10120.3C43—C42—H42118.9
C10—C11—C12122.2 (11)C41—C42—H42118.9
C10—C11—H11118.9C44—C43—C42118.9 (14)
C12—C11—H11118.9C44—C43—H43120.6
C17—C12—C13119.3 (12)C42—C43—H43120.6
C17—C12—C11120.5 (12)C45—C44—C43120.8 (16)
C13—C12—C11120.2 (11)C45—C44—H44119.6
C12—C13—C14117.8 (11)C43—C44—H44119.6
C12—C13—C8118.1 (11)C44—C45—C40121.9 (15)
C14—C13—C8124.1 (10)C44—C45—H45119.0
C15—C14—C13120.8 (11)C40—C45—H45119.0
C15—C14—H14119.6N4—C46—C47122.0 (9)
C13—C14—H14119.6N4—C46—H46119.0
C14—C15—C16122.3 (12)C47—C46—H46119.0
C14—C15—H15118.8C48—C47—C52121.3 (11)
C16—C15—H15118.8C48—C47—C46118.4 (10)
C17—C16—C15117.5 (12)C52—C47—C46120.3 (11)
C17—C16—H16121.2O4—C48—C47124.1 (11)
C15—C16—H16121.2O4—C48—C49118.5 (12)
C16—C17—C12122.1 (12)C47—C48—C49117.4 (12)
C16—C17—H17118.9C50—C49—C48121.1 (13)
C12—C17—H17118.9C50—C49—H49119.4
N2—C18—C19122.5 (9)C48—C49—H49119.4
N2—C18—H18118.8C49—C50—C51126.5 (14)
C19—C18—H18118.8C49—C50—H50116.7
C20—C19—C24116.9 (10)C51—C50—H50116.7
C20—C19—C18121.6 (10)C56—C51—C50127.6 (17)
C24—C19—C18121.5 (9)C56—C51—C52116.5 (14)
O2—C20—C19121.5 (10)C50—C51—C52115.9 (12)
O2—C20—C21115.5 (11)C53—C52—C47124.2 (12)
C19—C20—C21123.0 (11)C53—C52—C51118.1 (12)
C22—C21—C20119.5 (12)C47—C52—C51117.7 (12)
C22—C21—H21120.2C54—C53—C52120.7 (13)
C20—C21—H21120.2C54—C53—H53119.6
C21—C22—C23120.5 (13)C52—C53—H53119.6
C21—C22—H22119.8C53—C54—C55120.9 (14)
C23—C22—H22119.8C53—C54—H54119.6
C24—C23—C22118.5 (12)C55—C54—H54119.6
C24—C23—C28120.1 (13)C56—C55—C54117.0 (14)
C22—C23—C28121.4 (13)C56—C55—H55121.5
C23—C24—C25116.6 (11)C54—C55—H55121.5
C23—C24—C19121.5 (11)C55—C56—C51126.8 (17)
C25—C24—C19121.9 (10)C55—C56—H56116.6
C26—C25—C24121.5 (12)C51—C56—H56116.6
C26—C25—H25119.3C58—C57—O5117.4 (19)
C24—C25—H25119.3C58—C57—H57A108.0
C25—C26—C27122.0 (13)O5—C57—H57A108.0
C25—C26—H26119.0C58—C57—H57B108.0
C27—C26—H26119.0O5—C57—H57B108.0
C28—C27—C26117.5 (14)H57A—C57—H57B107.2
C28—C27—H27121.3C57—C58—H58A109.5
C26—C27—H27121.3C57—C58—H58B109.5
C27—C28—C23122.3 (14)H58A—C58—H58B109.5
C27—C28—H28118.9C57—C58—H58C109.5
C23—C28—H28118.9H58A—C58—H58C109.5
C30—C29—C34118.6 (10)H58B—C58—H58C109.5
C30—C29—N3116.8 (10)
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O30.821.992.790 (11)166
O4—H4···N40.821.872.594 (11)147
O3—H3···N30.821.812.550 (10)149
O2—H2···N20.821.852.578 (10)148
O1—H1···N10.821.792.535 (9)149

Experimental details

Crystal data
Chemical formulaC28H20N2O2·0.5(C2H6O)
Mr439.50
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)298
a, b, c (Å)19.956 (2), 12.4742 (13), 18.189 (2)
V3)4527.9 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.18 × 0.07
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.984, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections
21755, 4002, 1545
Rint0.176
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.094, 0.121, 1.06
No. of reflections4002
No. of parameters605
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.16

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected interatomic distances (Å) top
C8···C353.485 (16)C9···C47i3.402 (16)
C12···C343.387 (16)C13···C49i3.475 (16)
C15···C463.473 (15)C19···C37ii3.418 (15)
C1···C54i3.462 (17)C26···C29ii3.308 (17)
C7···C52i3.481 (15)
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O30.821.992.790 (11)165.9
O4—H4···N40.821.872.594 (11)147.0
O3—H3···N30.821.812.550 (10)148.9
O2—H2···N20.821.852.578 (10)147.7
O1—H1···N10.821.792.535 (9)149.4
 

Acknowledgements

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (grant No. X051040).

References

First citationEltayeb, N. E., Teoh, S. G., Teh, J. B.-J., Fun, H.-K. & Ibrahim, K. (2007). Acta Cryst. E63, o117–o119.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLo, W.-K., Wong, W.-K., Wong, W.-Y., Guo, J. P., Yeung, K.-T., Cheng, Y.-K., Yang, X. P. & Jones, R. A. (2006). Inorg. Chem. 45, 9315–9325.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationZhang, W., Loebach, J. L., Wilson, S. R. & Jacobsen, E. N. (1990). J. Am. Chem. Soc. 112, 2801–2804.  CSD CrossRef CAS Web of Science Google Scholar

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