PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o349–o350.
Published online 2009 January 17. doi:  10.1107/S1600536809001731
PMCID: PMC2968344

5-Diethyl­amino-2-[(E)-(4-methyl-3-nitro­phenyl)­imino­meth­yl]phenol: a redetermination

Abstract

The title compound, C18H21N3O3, is a potential bidentate Schiff base ligand. The whole mol­ecule is disordered with a refined site-occupancy ratio of 0.567 (4):0.433 (4) and not just one ethyl group as reported previously [Sarojini et al. (2007 [triangle]). Acta Cryst. E63, o4782–o4782]. Using the whole mol­ecule disorder, R values are much smaller than those published. An intra­molecular O—H(...)N hydrogen bond generates a six-membered ring, producing an S(6) ring motif. The dihedral angle between the mean plane of the two benzene rings (major component) is 9.0 (5)°. The crystal structure shows short C(...)C [3.189 (15)–3.298 (12) Å] and C(...)O [2.983 (5)–3.149 (13) Å] contacts. Inter­molecular C—H(...)O inter­actions link neighbouring mol­ecules into dimers with R 2 2(18) motifs. In the crystal structure, these dimers are linked together by inter­molecular C—H(...)O inter­actions into one-dimensional extended chains along the b axis. The crystal structure is further stabilized by inter­molecular π–π stacking inter­actions [centroid–centroid distances = 3.458 (8)–3.691 (6) Å].

Related literature

For the previous determination of this structure, see: Sarojini et al. (2007 [triangle]). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the application of Schiff bases in synthesis, coordination chemistry and biomedical activities, see: Patai (1970 [triangle]); Tai et al. (2003 [triangle]); Ittel et al. (2000 [triangle]); Kabeer et al. (2001 [triangle]); Pandeya et al. (1999 [triangle]); More et al. (2001 [triangle]); Singh & Dash (1988 [triangle]); Isloor et al. (2009 [triangle]); Pathak et al. (2000 [triangle]); Vazzanaa et al. (2004 [triangle]); Samadhiya & Halve (2001 [triangle]); Aydoğan et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o349-scheme1.jpg

Experimental

Crystal data

  • C18H21N3O3
  • M r = 327.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o349-efi1.jpg
  • a = 7.2777 (1) Å
  • b = 22.1792 (5) Å
  • c = 10.3473 (2) Å
  • β = 103.713 (1)°
  • V = 1622.59 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100.0 (1) K
  • 0.49 × 0.25 × 0.04 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.956, T max = 0.997
  • 21678 measured reflections
  • 4744 independent reflections
  • 3239 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.117
  • S = 1.02
  • 4744 reflections
  • 412 parameters
  • 1197 restraints
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001731/at2709sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001731/at2709Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/ 811012.

supplementary crystallographic information

Comment

Compounds with the structure of –C═N– (azomethine group) are known as Schiff bases, which are usually synthesized by the condensation of primary amines and active carbonyl groups. The chemistry of the carbon-nitrogen double bond plays a vital role in the progresses of chemistry (Patai 1970). They have been used as intermediates in medical substrates and as ligands in complex formation with some metal ions (Tai et al., 2003). Recently multi-dentate complexes of iron and nickel showed high activities of ethylene oligomerization and polymerization (Ittel et al., 2000). They have shown biological activities including antibacterial (Kabeer et al., 2001; Pandeya et al., 1999), antifungal (More et al., 2001; Singh & Dash 1988), anticancer (Isloor et al., 2009; Pathak et al., 2000), anti-inflammatory (Vazzanaa et al., 2004) and herbicidal (Samadhiya & Halve 2001) activities. In addition, Schiff bases have also been used as starting materials in the synthesis of large bioactive and industrial compounds via ring closure, cycloaddition and replacement reactions (Aydoğan et al., 2001).

In the title compound, (I), (Fig. 1), an intramolecular O—H···N hydrogen bond generate a six-membered ring, producing S(6) ring motif (Table 1). Intermolecular C—H···O interactions link neighbouring molecules into dimers with R22(18) motifs (Table 1, Fig. 2). The whole molecule is disordered with a site occupancy ratio of 0.567 (4)/0.433 (4) and not just the ethyl group as mentioned in the previously reported article (Sarojini et al., 2007). Using the whole molecule disorder, R-values are much smaller than those published.

The two substituted benzene rings are not coplanar and make a dihedral angle of 9.0 (5)° (for major component A). The interesting features of the crystal structure is short C1A···C8Ai [3.298 (12) Å;(i) 1-x,-y,2-z], C1B···C8Bi [3.329 (16) Å], C3B···C12Bi [3.189 (15) Å], C15A···O3Aii [2.983 (5) Å; (ii) 3/2-x,-1/2+y,3/2-z], C8B···O3Biii [3.149 Å; (iii) -x,-y,1-z], and C13B···O3Biii [3.116 (15) Å] contacts which are shorter than the sum of the van der Waals radii of these atoms. In the crystal structure, these dimers are linked together by intermolecular C—H···O interaction into 1-D extended chains along the b-axis (Fig. 3). The crystal structure is further stabilized by weak intermolecular π-π interactions [Cg1··· Cg2i = 3.7744 (6) Å; Cg2···Cg3i = 3.473 (7) Å; Cg3···Cg4i = 3.458 (8) Å and Cg1···Cg4 = 3.670 (7) Å: Cg1, Cg2, Cg3, and Cg4 are the centroids of the C1A–C6A, C8A–C13A, C1B–C6B, and C8B–C13B benzene rings].

Experimental

An equimolar mixture of 4-(diethylamino)-2-hydroxybenzaldehyde (0.5 g, 2.59 mmol) and 4-methyl-3-nitro aniline (0.393 g, 2.59 mmol) in ethanol (10 mL) were refluxed for 4 h. Catalytic amount of sulfuric acid was also added. The precipitated solid was filtered and recrystallised from acetone to yield orange coloured crystalline solid [0.41 g, 82 %, m.p 405 K]).

Refinement

H atoms of the hydroxy groups were positioned by a freely rotating O—H bond and constrained with a fixed distance of 0.84 Å. The rest of the hydrogen atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl hydrogen atoms of the methoxy groups. Rigid bond, similarity and simulation restraints were applied.

Figures

Fig. 1.
The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Intramolecular hydrogen bond is shown as a dashed line. Open bonds show the minor component.
Fig. 2.
The crystal packing of the major component of (I), viewed down the b-axis, showing dimer formation by a R22(18) motif.
Fig. 3.
The crystal packing of the major component of (I), viewed down the c-axis, showing 1-D extended chain along the b-axis.

Crystal data

C18H21N3O3F(000) = 696
Mr = 327.38Dx = 1.340 Mg m3
Monoclinic, P21/nMelting point: 405 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 7.2777 (1) ÅCell parameters from 4554 reflections
b = 22.1792 (5) Åθ = 2.7–29.8°
c = 10.3473 (2) ŵ = 0.09 mm1
β = 103.713 (1)°T = 100 K
V = 1622.59 (5) Å3Plate, yellow
Z = 40.49 × 0.25 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer4744 independent reflections
Radiation source: fine-focus sealed tube3239 reflections with I > 2σ(I)
graphiteRint = 0.037
[var phi] and ω scansθmax = 30.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −10→10
Tmin = 0.956, Tmax = 0.997k = −31→31
21678 measured reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0561P)2 + 0.1724P] where P = (Fo2 + 2Fc2)/3
4744 reflections(Δ/σ)max < 0.001
412 parametersΔρmax = 0.21 e Å3
1197 restraintsΔρmin = −0.22 e Å3

Special details

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/UeqOcc. (<1)
O1A0.3739 (19)0.0973 (10)1.0926 (17)0.0234 (9)0.567 (4)
H1A0.30890.07911.02620.035*0.567 (4)
C1A0.5374 (9)0.1157 (3)1.0663 (5)0.0125 (7)0.567 (4)
C2A0.647 (2)0.1575 (12)1.1497 (19)0.0255 (9)0.567 (4)
H2AA0.61400.16821.23010.031*0.567 (4)
C3A0.8077 (5)0.18510 (16)1.1189 (3)0.0255 (6)0.567 (4)
C4A0.8620 (5)0.16478 (18)1.0018 (4)0.0296 (7)0.567 (4)
H4AA0.97260.18030.98030.035*0.567 (4)
C5A0.7531 (7)0.1227 (3)0.9210 (6)0.0252 (10)0.567 (4)
H5AA0.79110.10990.84360.030*0.567 (4)
C6A0.5879 (14)0.0974 (8)0.9470 (12)0.0197 (10)0.567 (4)
C7A0.4817 (12)0.0550 (5)0.8538 (8)0.0179 (13)0.567 (4)
H7AA0.53000.04220.78070.021*0.567 (4)
N1A0.3211 (11)0.0336 (5)0.8673 (8)0.0179 (9)0.567 (4)
C8A0.2039 (12)−0.0048 (5)0.7729 (8)0.0250 (14)0.567 (4)
C9A0.2462 (14)−0.0271 (7)0.6580 (10)0.0230 (14)0.567 (4)
H9AA0.3631−0.01710.63760.028*0.567 (4)
C10A0.1184 (11)−0.0637 (5)0.5730 (8)0.0221 (11)0.567 (4)
C11A−0.0553 (11)−0.0821 (6)0.5965 (9)0.0226 (11)0.567 (4)
C12A−0.0955 (14)−0.0564 (5)0.7096 (9)0.0309 (12)0.567 (4)
H12A−0.2169−0.06370.72560.037*0.567 (4)
C13A0.0291 (11)−0.0210 (5)0.8002 (9)0.0264 (12)0.567 (4)
H13A−0.0024−0.00780.87960.032*0.567 (4)
N2A0.9119 (3)0.22760 (14)1.1993 (3)0.0402 (7)0.567 (4)
C14A1.1461 (3)0.22808 (9)1.21715 (19)0.0262 (5)0.567 (4)
H14A1.21680.23691.30930.031*0.567 (4)
H14B1.19420.19081.18430.031*0.567 (4)
C15A1.1392 (3)0.28153 (10)1.1233 (2)0.0327 (6)0.567 (4)
H15A1.26770.29121.11580.049*0.567 (4)
H15B1.08470.31651.15850.049*0.567 (4)
H15C1.06090.27121.03530.049*0.567 (4)
C16A0.8713 (9)0.2448 (3)1.3260 (6)0.0268 (11)0.567 (4)
H16A0.99000.25801.38810.032*0.567 (4)
H16B0.82320.20921.36550.032*0.567 (4)
C17A0.7284 (9)0.2947 (3)1.3107 (9)0.0343 (11)0.567 (4)
H17A0.70580.30471.39790.052*0.567 (4)
H17B0.60970.28161.25090.052*0.567 (4)
H17C0.77640.33041.27340.052*0.567 (4)
C18A−0.1980 (12)−0.1223 (4)0.5104 (10)0.0286 (13)0.567 (4)
H18A−0.3071−0.12700.54980.043*0.567 (4)
H18B−0.1412−0.16190.50340.043*0.567 (4)
H18C−0.2394−0.10450.42160.043*0.567 (4)
N3A0.184 (3)−0.0827 (19)0.455 (2)0.0313 (14)0.567 (4)
O2A0.3440 (11)−0.0694 (3)0.4470 (8)0.0529 (17)0.567 (4)
O3A0.0868 (6)−0.1188 (2)0.3802 (5)0.0700 (13)0.567 (4)
O1B0.398 (3)0.0963 (13)1.092 (2)0.0234 (9)0.433 (4)
H1B0.35510.06801.03910.035*0.433 (4)
C1B0.5589 (14)0.1191 (5)1.0618 (9)0.0306 (17)0.433 (4)
C2B0.665 (3)0.1575 (15)1.155 (2)0.0255 (9)0.433 (4)
H2BA0.61480.17411.22350.031*0.433 (4)
C3B0.8515 (5)0.17175 (19)1.1452 (4)0.0181 (7)0.433 (4)
C4B0.9079 (6)0.1517 (2)1.0301 (4)0.0218 (8)0.433 (4)
H4BA1.02770.16361.01720.026*0.433 (4)
C5B0.7946 (8)0.1158 (4)0.9378 (8)0.0221 (11)0.433 (4)
H5BA0.83740.10340.86200.027*0.433 (4)
C6B0.6180 (19)0.0966 (10)0.9512 (17)0.0197 (10)0.433 (4)
C7B0.4953 (17)0.0590 (7)0.8598 (12)0.030 (2)0.433 (4)
H7BA0.53340.04630.78240.036*0.433 (4)
N1B0.3323 (17)0.0409 (7)0.8762 (12)0.0250 (18)0.433 (4)
C8B0.2194 (14)0.0014 (6)0.7836 (10)0.0169 (13)0.433 (4)
C9B0.2642 (19)−0.0211 (9)0.6684 (14)0.0189 (13)0.433 (4)
H9BA0.3822−0.01170.64910.023*0.433 (4)
C10B0.1362 (14)−0.0571 (6)0.5834 (10)0.0213 (14)0.433 (4)
C11B−0.0420 (16)−0.0732 (8)0.6030 (12)0.028 (2)0.433 (4)
C12B−0.0749 (16)−0.0544 (7)0.7258 (11)0.0330 (19)0.433 (4)
H12B−0.1823−0.06880.75360.040*0.433 (4)
C13B0.0489 (16)−0.0153 (7)0.8050 (13)0.033 (2)0.433 (4)
H13B0.01310.00130.88000.040*0.433 (4)
N2B0.9676 (3)0.20711 (11)1.2388 (2)0.0158 (5)0.433 (4)
C14B1.0549 (4)0.26562 (12)1.1520 (3)0.0288 (7)0.433 (4)
H14C1.00150.26541.05470.035*0.433 (4)
H14D1.04820.30631.18990.035*0.433 (4)
C15B1.2453 (4)0.23619 (13)1.1946 (3)0.0343 (8)0.433 (4)
H15D1.33810.25931.16020.051*0.433 (4)
H15E1.23840.19501.15950.051*0.433 (4)
H15F1.28390.23501.29200.051*0.433 (4)
C16B0.9026 (12)0.2355 (5)1.3477 (7)0.0245 (12)0.433 (4)
H16C1.01440.24901.41620.029*0.433 (4)
H16D0.83560.20501.38910.029*0.433 (4)
C17B0.7722 (11)0.2891 (4)1.3056 (11)0.0315 (13)0.433 (4)
H17D0.73390.30541.38320.047*0.433 (4)
H17E0.65980.27611.23890.047*0.433 (4)
H17F0.83880.32031.26740.047*0.433 (4)
C18B−0.1932 (17)−0.1105 (6)0.5125 (13)0.0300 (17)0.433 (4)
H18D−0.3026−0.11430.55180.045*0.433 (4)
H18E−0.1429−0.15070.50140.045*0.433 (4)
H18F−0.2320−0.09070.42560.045*0.433 (4)
N3B0.185 (4)−0.078 (2)0.459 (3)0.0313 (14)0.433 (4)
O2B0.3391 (12)−0.0633 (4)0.4405 (10)0.0260 (11)0.433 (4)
O3B0.0621 (6)−0.10006 (19)0.3677 (5)0.0255 (7)0.433 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.020 (3)0.0286 (7)0.0251 (4)−0.003 (2)0.0111 (17)−0.0049 (4)
C1A0.0190 (15)0.0127 (15)0.0082 (12)0.0006 (11)0.0079 (10)−0.0015 (10)
C2A0.031 (2)0.0267 (5)0.0230 (12)−0.0060 (19)0.0144 (18)−0.0060 (8)
C3A0.0251 (15)0.0271 (17)0.0258 (16)−0.0008 (11)0.0091 (11)−0.0056 (12)
C4A0.0284 (16)0.034 (2)0.0314 (18)−0.0034 (12)0.0175 (13)−0.0041 (13)
C5A0.026 (2)0.0303 (18)0.0211 (16)0.0044 (15)0.0082 (14)−0.0067 (14)
C6A0.019 (3)0.0228 (6)0.0184 (8)0.003 (2)0.0072 (19)0.0009 (7)
C7A0.027 (2)0.0150 (18)0.0087 (19)0.0030 (15)−0.0020 (15)−0.0034 (16)
N1A0.0219 (19)0.018 (2)0.0152 (18)0.0029 (12)0.0063 (15)−0.0020 (14)
C8A0.0211 (17)0.024 (2)0.024 (2)0.0017 (13)−0.0067 (14)−0.0046 (14)
C9A0.020 (3)0.035 (4)0.015 (2)0.0024 (18)0.005 (2)−0.0029 (15)
C10A0.0218 (18)0.024 (2)0.0150 (15)0.0008 (14)−0.0058 (11)−0.0054 (13)
C11A0.019 (2)0.030 (3)0.020 (2)0.0001 (15)0.0067 (16)−0.0031 (14)
C12A0.0195 (16)0.043 (2)0.026 (2)−0.0028 (14)−0.0026 (13)−0.0072 (17)
C13A0.0192 (16)0.039 (3)0.026 (3)0.0015 (15)0.0150 (19)−0.0062 (17)
N2A0.0351 (12)0.0537 (17)0.0389 (14)−0.0199 (11)0.0227 (10)−0.0212 (12)
C14A0.0232 (10)0.0282 (10)0.0292 (10)−0.0032 (8)0.0105 (8)−0.0030 (8)
C15A0.0344 (11)0.0308 (11)0.0390 (11)−0.0074 (9)0.0208 (9)0.0020 (9)
C16A0.023 (2)0.033 (3)0.0247 (19)−0.0049 (15)0.0064 (15)−0.0040 (16)
C17A0.032 (3)0.0292 (18)0.0424 (18)0.0006 (16)0.0093 (18)0.0078 (14)
C18A0.0211 (15)0.030 (3)0.0303 (18)−0.0061 (16)−0.0038 (12)−0.0059 (18)
N3A0.0284 (5)0.044 (5)0.0211 (13)−0.0034 (11)0.0058 (7)−0.0080 (7)
O2A0.028 (2)0.092 (4)0.040 (3)−0.001 (2)0.0118 (18)−0.028 (3)
O3A0.083 (3)0.087 (3)0.052 (2)−0.0527 (19)0.0408 (18)−0.047 (2)
O1B0.020 (3)0.0286 (7)0.0251 (4)−0.003 (2)0.0111 (17)−0.0049 (4)
C1B0.023 (2)0.029 (3)0.043 (3)−0.0032 (18)0.0160 (18)0.0165 (19)
C2B0.031 (2)0.0267 (5)0.0230 (12)−0.0060 (19)0.0144 (18)−0.0060 (8)
C3B0.0189 (16)0.0160 (16)0.0188 (16)0.0090 (10)0.0033 (11)0.0086 (11)
C4B0.0216 (17)0.0228 (18)0.0221 (17)0.0055 (12)0.0072 (12)0.0046 (12)
C5B0.017 (2)0.029 (2)0.024 (2)0.0043 (18)0.0121 (18)0.0053 (15)
C6B0.019 (3)0.0228 (6)0.0184 (8)0.003 (2)0.0072 (19)0.0009 (7)
C7B0.031 (3)0.031 (4)0.032 (5)0.007 (2)0.017 (3)0.009 (3)
N1B0.028 (2)0.020 (3)0.021 (2)0.0010 (16)−0.0066 (16)−0.0077 (16)
C8B0.019 (3)0.025 (3)0.0084 (19)0.0045 (18)0.0057 (19)−0.0035 (16)
C9B0.0133 (18)0.021 (2)0.018 (2)−0.0030 (15)−0.0052 (15)−0.0053 (17)
C10B0.016 (2)0.036 (4)0.014 (2)−0.0026 (17)0.008 (2)−0.0050 (18)
C11B0.023 (2)0.029 (4)0.026 (2)−0.0086 (18)−0.0078 (17)−0.0045 (19)
C12B0.019 (3)0.063 (4)0.020 (3)−0.003 (2)0.011 (3)−0.006 (2)
C13B0.031 (3)0.043 (4)0.021 (3)−0.001 (2)−0.0029 (19)−0.008 (3)
N2B0.0172 (9)0.0156 (11)0.0132 (10)0.0058 (7)0.0011 (7)0.0053 (8)
C14B0.0297 (14)0.0258 (14)0.0327 (14)−0.0003 (11)0.0111 (11)−0.0025 (11)
C15B0.0268 (15)0.0375 (16)0.0411 (16)−0.0004 (11)0.0128 (12)−0.0035 (12)
C16B0.024 (3)0.030 (3)0.020 (2)0.0050 (16)0.0061 (18)−0.0041 (19)
C17B0.027 (3)0.031 (2)0.038 (2)−0.003 (2)0.009 (2)−0.0073 (17)
C18B0.033 (2)0.027 (4)0.032 (3)−0.008 (2)0.0111 (18)−0.002 (2)
N3B0.0284 (5)0.044 (5)0.0211 (13)−0.0034 (11)0.0058 (7)−0.0080 (7)
O2B0.023 (2)0.0343 (19)0.023 (2)−0.0071 (15)0.0100 (17)−0.0035 (16)
O3B0.0187 (9)0.0372 (17)0.0163 (10)0.0021 (11)−0.0043 (7)−0.0078 (11)

Geometric parameters (Å, °)

O1A—C1A1.346 (7)O1B—C1B1.376 (9)
O1A—H1A0.8400O1B—H1B0.8400
C1A—C2A1.384 (7)C1B—C2B1.377 (10)
C1A—C6A1.427 (7)C1B—C6B1.406 (9)
C2A—C3A1.420 (8)C2B—C3B1.418 (10)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—N2A1.363 (4)C3B—N2B1.371 (5)
C3A—C4A1.433 (5)C3B—C4B1.420 (6)
C4A—C5A1.373 (6)C4B—C5B1.361 (8)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.409 (7)C5B—C6B1.391 (8)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.436 (7)C6B—C7B1.409 (9)
C7A—N1A1.299 (7)C7B—N1B1.301 (9)
C7A—H7AA0.9500C7B—H7BA0.9500
N1A—C8A1.419 (7)N1B—C8B1.410 (9)
C8A—C9A1.388 (7)C8B—C13B1.363 (9)
C8A—C13A1.413 (7)C8B—C9B1.401 (9)
C9A—C10A1.383 (7)C9B—C10B1.375 (9)
C9A—H9AA0.9500C9B—H9BA0.9500
C10A—C11A1.403 (6)C10B—C11B1.405 (8)
C10A—N3A1.474 (7)C10B—N3B1.484 (9)
C11A—C12A1.394 (7)C11B—C12B1.410 (9)
C11A—C18A1.493 (7)C11B—C18B1.512 (9)
C12A—C13A1.384 (7)C12B—C13B1.373 (9)
C12A—H12A0.9500C12B—H12B0.9500
C13A—H13A0.9500C13B—H13B0.9500
N2A—C16A1.462 (6)N2B—C16B1.463 (8)
N2A—C14A1.670 (3)N2B—C14B1.779 (4)
C14A—C15A1.526 (3)C14B—C15B1.501 (4)
C14A—H14A0.9900C14B—H14C0.9900
C14A—H14B0.9900C14B—H14D0.9900
C15A—H15A0.9800C15B—H15D0.9800
C15A—H15B0.9800C15B—H15E0.9800
C15A—H15C0.9800C15B—H15F0.9800
C16A—C17A1.501 (6)C16B—C17B1.518 (8)
C16A—H16A0.9900C16B—H16C0.9900
C16A—H16B0.9900C16B—H16D0.9900
C17A—H17A0.9800C17B—H17D0.9800
C17A—H17B0.9800C17B—H17E0.9800
C17A—H17C0.9800C17B—H17F0.9800
C18A—H18A0.9800C18B—H18D0.9800
C18A—H18B0.9800C18B—H18E0.9800
C18A—H18C0.9800C18B—H18F0.9800
N3A—O3A1.219 (10)N3B—O2B1.225 (9)
N3A—O2A1.220 (7)N3B—O3B1.242 (13)
O1A—C1A—C2A119.0 (8)O1B—C1B—C2B115.9 (10)
O1A—C1A—C6A120.7 (7)O1B—C1B—C6B119.6 (10)
C2A—C1A—C6A120.0 (6)C2B—C1B—C6B123.9 (9)
C1A—C2A—C3A122.2 (8)C1B—C2B—C3B118.5 (10)
C1A—C2A—H2AA118.9C1B—C2B—H2BA120.7
C3A—C2A—H2AA118.9C3B—C2B—H2BA120.7
N2A—C3A—C2A121.9 (4)N2B—C3B—C2B121.2 (6)
N2A—C3A—C4A120.6 (3)N2B—C3B—C4B121.3 (4)
C2A—C3A—C4A117.4 (5)C2B—C3B—C4B117.3 (6)
C5A—C4A—C3A119.6 (4)C5B—C4B—C3B121.6 (5)
C5A—C4A—H4AA120.2C5B—C4B—H4BA119.2
C3A—C4A—H4AA120.2C3B—C4B—H4BA119.2
C4A—C5A—C6A123.3 (5)C4B—C5B—C6B122.0 (7)
C4A—C5A—H5AA118.4C4B—C5B—H5BA119.0
C6A—C5A—H5AA118.4C6B—C5B—H5BA119.0
C5A—C6A—C1A117.3 (6)C5B—C6B—C1B116.1 (8)
C5A—C6A—C7A118.7 (6)C5B—C6B—C7B124.6 (9)
C1A—C6A—C7A124.0 (6)C1B—C6B—C7B119.2 (8)
N1A—C7A—C6A121.5 (7)N1B—C7B—C6B123.2 (10)
N1A—C7A—H7AA119.3N1B—C7B—H7BA118.4
C6A—C7A—H7AA119.3C6B—C7B—H7BA118.4
C7A—N1A—C8A123.7 (6)C7B—N1B—C8B120.4 (9)
C9A—C8A—C13A118.3 (6)C13B—C8B—C9B116.5 (8)
C9A—C8A—N1A125.7 (6)C13B—C8B—N1B117.7 (8)
C13A—C8A—N1A116.0 (6)C9B—C8B—N1B125.8 (8)
C10A—C9A—C8A120.1 (6)C10B—C9B—C8B119.5 (9)
C10A—C9A—H9AA119.9C10B—C9B—H9BA120.2
C8A—C9A—H9AA119.9C8B—C9B—H9BA120.2
C9A—C10A—C11A124.0 (6)C9B—C10B—C11B124.3 (7)
C9A—C10A—N3A113.1 (6)C9B—C10B—N3B117.9 (7)
C11A—C10A—N3A123.0 (6)C11B—C10B—N3B117.8 (8)
C12A—C11A—C10A113.8 (6)C10B—C11B—C12B114.5 (7)
C12A—C11A—C18A119.4 (6)C10B—C11B—C18B127.6 (9)
C10A—C11A—C18A126.7 (6)C12B—C11B—C18B117.8 (9)
C13A—C12A—C11A124.5 (7)C13B—C12B—C11B119.8 (8)
C13A—C12A—H12A117.7C13B—C12B—H12B120.1
C11A—C12A—H12A117.7C11B—C12B—H12B120.1
C12A—C13A—C8A119.1 (6)C8B—C13B—C12B124.6 (9)
C12A—C13A—H13A120.5C8B—C13B—H13B117.7
C8A—C13A—H13A120.5C12B—C13B—H13B117.7
C3A—N2A—C16A121.8 (4)C3B—N2B—C16B122.2 (5)
C3A—N2A—C14A118.5 (2)C3B—N2B—C14B107.1 (2)
C16A—N2A—C14A108.5 (3)C16B—N2B—C14B107.1 (5)
C15A—C14A—N2A93.22 (16)C15B—C14B—N2B87.1 (2)
C15A—C14A—H14A113.1C15B—C14B—H14C114.1
N2A—C14A—H14A113.1N2B—C14B—H14C114.1
C15A—C14A—H14B113.1C15B—C14B—H14D114.1
N2A—C14A—H14B113.1N2B—C14B—H14D114.1
H14A—C14A—H14B110.5H14C—C14B—H14D111.3
C14A—C15A—H15A109.5C14B—C15B—H15D109.5
C14A—C15A—H15B109.5C14B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
C14A—C15A—H15C109.5C14B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
N2A—C16A—C17A112.4 (4)N2B—C16B—C17B114.2 (6)
N2A—C16A—H16A109.1N2B—C16B—H16C108.7
C17A—C16A—H16A109.1C17B—C16B—H16C108.7
N2A—C16A—H16B109.1N2B—C16B—H16D108.7
C17A—C16A—H16B109.1C17B—C16B—H16D108.7
H16A—C16A—H16B107.9H16C—C16B—H16D107.6
C16A—C17A—H17A109.5C16B—C17B—H17D109.5
C16A—C17A—H17B109.5C16B—C17B—H17E109.5
H17A—C17A—H17B109.5H17D—C17B—H17E109.5
C16A—C17A—H17C109.5C16B—C17B—H17F109.5
H17A—C17A—H17C109.5H17D—C17B—H17F109.5
H17B—C17A—H17C109.5H17E—C17B—H17F109.5
C11A—C18A—H18A109.5C11B—C18B—H18D109.5
C11A—C18A—H18B109.5C11B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C11A—C18A—H18C109.5C11B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
O3A—N3A—O2A122.4 (11)O2B—N3B—O3B120.2 (13)
O3A—N3A—C10A117.3 (8)O2B—N3B—C10B118.2 (9)
O2A—N3A—C10A119.3 (7)O3B—N3B—C10B120.4 (11)
C1B—O1B—H1B109.5
O1A—C1A—C2A—C3A−171 (2)O1B—C1B—C2B—C3B166 (3)
C6A—C1A—C2A—C3A2(3)C6B—C1B—C2B—C3B−5(4)
C1A—C2A—C3A—N2A178.0 (16)C1B—C2B—C3B—N2B−176 (2)
C1A—C2A—C3A—C4A−5(3)C1B—C2B—C3B—C4B8(4)
N2A—C3A—C4A—C5A−178.9 (4)N2B—C3B—C4B—C5B178.9 (4)
C2A—C3A—C4A—C5A3.6 (15)C2B—C3B—C4B—C5B−6(2)
C3A—C4A—C5A—C6A−0.3 (12)C3B—C4B—C5B—C6B−0.2 (16)
C4A—C5A—C6A—C1A−2(2)C4B—C5B—C6B—C1B3(3)
C4A—C5A—C6A—C7A178.3 (10)C4B—C5B—C6B—C7B−179.4 (17)
O1A—C1A—C6A—C5A174.7 (16)O1B—C1B—C6B—C5B−172 (2)
C2A—C1A—C6A—C5A1(2)C2B—C1B—C6B—C5B0(4)
O1A—C1A—C6A—C7A−6(2)O1B—C1B—C6B—C7B11 (3)
C2A—C1A—C6A—C7A−179 (2)C2B—C1B—C6B—C7B−178 (3)
C5A—C6A—C7A—N1A−174.8 (13)C5B—C6B—C7B—N1B179 (2)
C1A—C6A—C7A—N1A6(2)C1B—C6B—C7B—N1B−4(3)
C6A—C7A—N1A—C8A175.0 (14)C6B—C7B—N1B—C8B−177.5 (19)
C7A—N1A—C8A—C9A3(2)C7B—N1B—C8B—C13B−179.1 (17)
C7A—N1A—C8A—C13A−176.6 (12)C7B—N1B—C8B—C9B−1(3)
C13A—C8A—C9A—C10A0(2)C13B—C8B—C9B—C10B1(3)
N1A—C8A—C9A—C10A−179.3 (13)N1B—C8B—C9B—C10B−176.9 (17)
C8A—C9A—C10A—C11A−2(2)C8B—C9B—C10B—C11B1(3)
C8A—C9A—C10A—N3A179 (2)C8B—C9B—C10B—N3B177 (3)
C9A—C10A—C11A—C12A4.5 (19)C9B—C10B—C11B—C12B−6(3)
N3A—C10A—C11A—C12A−177 (2)N3B—C10B—C11B—C12B177 (3)
C9A—C10A—C11A—C18A−178.9 (13)C9B—C10B—C11B—C18B177.7 (18)
N3A—C10A—C11A—C18A0(3)N3B—C10B—C11B—C18B1(4)
C10A—C11A—C12A—C13A−6.6 (19)C10B—C11B—C12B—C13B10 (2)
C18A—C11A—C12A—C13A176.6 (12)C18B—C11B—C12B—C13B−173.2 (15)
C11A—C12A—C13A—C8A6(2)C9B—C8B—C13B—C12B3(3)
C9A—C8A—C13A—C12A−2.3 (19)N1B—C8B—C13B—C12B−178.4 (16)
N1A—C8A—C13A—C12A177.4 (11)C11B—C12B—C13B—C8B−9(3)
C2A—C3A—N2A—C16A3.6 (16)C2B—C3B—N2B—C16B−4(2)
C4A—C3A—N2A—C16A−173.8 (3)C4B—C3B—N2B—C16B170.9 (5)
C2A—C3A—N2A—C14A143.3 (15)C2B—C3B—N2B—C14B−128 (2)
C4A—C3A—N2A—C14A−34.1 (4)C4B—C3B—N2B—C14B47.0 (3)
C3A—N2A—C14A—C15A102.7 (3)C3B—N2B—C14B—C15B−111.2 (2)
C16A—N2A—C14A—C15A−112.8 (4)C16B—N2B—C14B—C15B116.1 (4)
C3A—N2A—C16A—C17A−88.1 (6)C3B—N2B—C16B—C17B−74.0 (9)
C14A—N2A—C16A—C17A128.8 (5)C14B—N2B—C16B—C17B49.9 (8)
C9A—C10A—N3A—O3A175 (3)C9B—C10B—N3B—O2B2(6)
C11A—C10A—N3A—O3A−4(5)C11B—C10B—N3B—O2B179 (4)
C9A—C10A—N3A—O2A5(5)C9B—C10B—N3B—O3B−166 (4)
C11A—C10A—N3A—O2A−174 (3)C11B—C10B—N3B—O3B11 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1A—H1A···N1A0.841.952.68 (2)144
C12A—H12A···O1Ai0.952.533.329 (19)141
C15A—H15A···O3Aii0.982.262.983 (5)130

Symmetry codes: (i) −x, −y, −z+2; (ii) −x+3/2, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2709).

References

  • Aydoğan, F., Öcal, N., Turgut, Z. & Yolaçan, C. (2001). Bull. Korean Chem. Soc 22, 476–480.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Isloor, A. M., Sunil, D., Shetty, P. & Satyamoorthy, K. (2009). Eur. J. Med. Chem. Submitted.
  • Ittel, S. D., Johnson, L. K. & Brookhart, M. (2000). Chem. Rev. 100, 1169–1203. [PubMed]
  • Kabeer, A. S., Baseer, M. A. & Mote, N. A. (2001). Asian J. Chem.13, 496–500.
  • More, P. G., Bhalvankar, R. B. & Pattar, S. C. (2001). J. Indian Chem. Soc.78, 474–475.
  • Pandeya, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Farmaco, 54, 624–628. [PubMed]
  • Patai, S. (1970). The Chemistry of the Carbon–Nitrogen Double Bond London: John Wiley & Sons Ltd.
  • Pathak, P., Jolly, V. S. & Sharma, K. P. (2000). Orient. J. Chem 16, 161–162.
  • Samadhiya, S. & Halve, A. (2001). Orient. J. Chem 17, 119–122.
  • Sarojini, B. K., Narayana, B., Mustafa, K., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o4782.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33–37.
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Tai, X., Yin, X., Chen, Q. & Tan, M. (2003). Molecules, 8, 439–443.
  • Vazzanaa, I., Terranova, E., Mattiolib, F. & Sparatore, F. (2004). Arkivoc, v, 364–374.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography