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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o89–o90.
Published online 2009 December 9. doi:  10.1107/S160053680905209X
PMCID: PMC2980163

(E)-4-(4-Hydr­oxy-3-methoxy­benzyl­idene­amino)-3-[1-(4-isobutyl­phen­yl)eth­yl]-1H-1,2,4-triazole-5(4H)-thione

Abstract

The asymmetric unit of the title compound, C22H26N4O2S, contains two crystallographically independent mol­ecules (A and B). The isobutyl unit of mol­ecule B is disordered over two orientations with refined occupancies of 0.785 (6) and 0.215 (6). In each mol­ecule, intra­molecular C—H(...)S hydrogen bonds generate S(6) ring motifs. The essentially planar 1,2,4-triazole rings [r.m.s. deviations of 0.004 (2) and 0.011 (2) Å, in A and B respectively] form dihedral angles of 85.86 (12), 8.38 (10)°, respectively, with the isobutyl-substituted phenyl ring and the 2-methoxy­phenol substituent in mol­ecule A [89.26 (13) and 2.46 (10)°, respectively, in B]. In the crystal structure, inter­molecular N—H(...)N and N—H(...)S hydrogen bonds link neighbouring mol­ecules, generating R 2 2(7) ring motifs. These molecules are further inter­connected into extended chains along [20An external file that holds a picture, illustration, etc.
Object name is e-66-00o89-efi2.jpg] by inter­molecular O—H(...)O hydrogen bonds. The crystal structure is further stabilized by π–π [centroid-centroid distance = 3.6299 (13) Å] and C—H(...)π inter­actions. A short O(...)O contact of 2.781 (2) Å is also observed.

Related literature

For general background to and applications of the title compound, see: Bekircan & Bektas (2006 [triangle]); Fun et al. (2009 [triangle]); Koparır et al. (2005 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For a closely related 1,2,4-triazole structure, see: Fun et al. (2009 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00o89-scheme1.jpg

Experimental

Crystal data

  • C22H26N4O2S
  • M r = 410.53
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o89-efi3.jpg
  • a = 9.8646 (3) Å
  • b = 14.2026 (5) Å
  • c = 16.6758 (6) Å
  • α = 69.048 (2)°
  • β = 79.881 (2)°
  • γ = 85.946 (2)°
  • V = 2147.83 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.18 mm−1
  • T = 100 K
  • 0.31 × 0.22 × 0.15 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.948, T max = 0.974
  • 39640 measured reflections
  • 7435 independent reflections
  • 5503 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.111
  • S = 1.04
  • 7435 reflections
  • 571 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.25 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, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905209X/sj2704sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905209X/sj2704Isup2.hkl

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

Acknowledgments

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship.

supplementary crystallographic information

Comment

1,2,4-triazoles and their derivatives are found to be associated with various biological activities with for example anti-convulsant, anti-fungal, anti-cancer, anti-inflammatory, anti-bacterial properties (Bekircan & Bektas, 2006) and also act as effective pesticides (Koparır et al., 2005). Several compounds containing 1,2,4-triazole rings are well known as drugs. Furthermore, in recent years, some Schiff base derivatives of 1,2,4-triazoles have been found to possess pharmacological activities (Fun et al., 2009). As part of our ongoing work on Schiff base derivatives, we report here the crystal structure of this new Schiff base.

In the asymmetric unit of the title 1,2,4-triazole compound, there are two crystallographically independent molecules, designated A and B (Fig. 1). In molecule B, the isobutyl unit is disordered over two positions with a refined site-occupancy ratio of 0.785 (6):0.215 (6). In each molecule, intramolecular C7A—H7AA···S1A and C7B—H7BA···S1B hydrogen bonds (Table 1) generate six-membered rings, producing S(6) ring motifs (Fig. 1, Bernstein et al., 1995). The 1,2,4-triazole rings (N2/C8/N3/N4/C9) are essentially planar, with maximum deviations of -0.004 (2) and -0.011 (2) Å, respectively, for atoms C8A and C8B. In molecule A, the 1,2,4-triazole ring makes dihedral angles of 85.86 (12) and 8.38 (10)°, respectively, with isobutyl-substituted phenyl ring (C11-C16) and 2-methoxyphenol moiety (C1-C6/C21/O1/O2); the comparable angles for molecule B are 89.26 (13) and 2.46 (10)°, respectively. The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to a closely related structure (Fun et al., 2009).

In the crystal structure (Fig. 2), intermolecular N3A—H1N3···N4B and N3B—H2N3···S1A hydrogen bonds (Table 1) link neighbouring molecules into R22(7) ring motifs (Bernstein et al., 1995). Intermolecular O2A—H1O2···O2B hydrogen bonds (Table 1) interconnect these hydrogen bond ring motifs into one-dimensional extended chains along [201]. An interesting feature of the crystal structure is the short intermolecular O1A···O2B contacts [symmetry code: -1+x, y, 1+z] with a distance of 2.781 (2) Å, which is significantly shorter than the sum of the van der Waals radii of the oxygen atoms (3.04 Å). The crystal structure is further stabilized by intermolecular C5B—H5BA···Cg1 as well as Cg2···Cg3 interactions [centroid-centroid distance = 3.6299 (13) Åiv; Cg1, Cg2 and Cg3 are the centroids of C11A-C16A, C1A-C6A and C1B-C6B phenyl rings, respectively].

Experimental

The title Schiff base compound was obtained by refluxing 4-amino-5-[1-(4-isobutylphenyl)ethyl]-4H-1,2,4-triazole-3-thiol (0.01 mol) and 4-hydroxy-3-methoxybenzaldehyde (0.01 mol) in ethanol (20 ml) for 6 h, with the addition of three drops of concentrated sulphuric acid. The solid product obtained was collected by filtration, washed with ethanol and dried. It was then recrystallized using ethanol. Single crystals suitable for X-ray analysis were obtained from ethanol by slow evaporation.

Refinement

Atoms H1N3, H2N3, H1O2 and H2O2 were located from difference Fourier map and allowed to refine freely. All other hydrogen atoms were placed in their calculated positions, with C—H = 0.93 – 0.98 Å, and refined using a riding model, with Uiso = 1.2 or 1.5 Ueq(C). A rotating group model was used for the methyl groups. The isobutyl unit of molecule B is disordered over two positions with refined occupancies of 0.785 (6) and 0.215 (6). The same Uij parameters were used for the atom pair C19B/C19C. The reflection (010) was omitted as the intensity was affected by the beam backstop.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. Intramolecular hydrogen bonds are shown as dashed lines. Open bonds indicate the minor disorder component.
Fig. 2.
The crystal structure of the title compound, showing R22(7) ring motifs being linked into one-dimensional extended chains. Only the major disorder component is shown. H atoms not involved in intermolecular interactions (dashed lines) have been omitted ...

Crystal data

C22H26N4O2SZ = 4
Mr = 410.53F(000) = 872
Triclinic, P1Dx = 1.270 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8646 (3) ÅCell parameters from 9988 reflections
b = 14.2026 (5) Åθ = 2.5–29.9°
c = 16.6758 (6) ŵ = 0.18 mm1
α = 69.048 (2)°T = 100 K
β = 79.881 (2)°Block, colourless
γ = 85.946 (2)°0.31 × 0.22 × 0.15 mm
V = 2147.83 (13) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer7435 independent reflections
Radiation source: fine-focus sealed tube5503 reflections with I > 2σ(I)
graphiteRint = 0.060
[var phi] and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −11→11
Tmin = 0.948, Tmax = 0.974k = −16→16
39640 measured reflectionsl = −19→19

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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0383P)2 + 1.5959P] where P = (Fo2 + 2Fc2)/3
7435 reflections(Δ/σ)max = 0.001
571 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = −0.25 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.
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)
S1A0.14118 (6)1.03163 (5)0.30146 (4)0.02423 (16)
O1A0.82404 (16)0.95561 (12)−0.02253 (10)0.0245 (4)
O2A0.87801 (18)1.15369 (14)−0.06581 (11)0.0279 (4)
N1A0.36062 (18)0.90569 (15)0.18842 (12)0.0211 (5)
N2A0.24185 (18)0.87048 (14)0.25021 (12)0.0191 (4)
N3A0.0621 (2)0.83823 (15)0.34536 (13)0.0224 (5)
N4A0.09167 (19)0.75035 (15)0.32812 (12)0.0241 (5)
C1A0.6112 (2)0.97179 (17)0.07204 (14)0.0197 (5)
H1AA0.58970.90420.08760.024*
C2A0.7294 (2)1.01022 (17)0.01489 (14)0.0196 (5)
C3A0.7613 (2)1.11248 (17)−0.00986 (14)0.0199 (5)
C4A0.6741 (2)1.17468 (18)0.02374 (15)0.0227 (5)
H4AA0.69441.24260.00690.027*
C5A0.5561 (2)1.13561 (18)0.08250 (15)0.0234 (6)
H5AA0.49861.17740.10580.028*
C6A0.5232 (2)1.03453 (17)0.10683 (14)0.0196 (5)
C7A0.3988 (2)0.99654 (18)0.16938 (15)0.0218 (5)
H7AA0.34721.03830.19550.026*
C8A0.1491 (2)0.91387 (18)0.29956 (14)0.0202 (5)
C9A0.2026 (2)0.77220 (18)0.26948 (15)0.0220 (5)
C10A0.2820 (2)0.70098 (18)0.23134 (16)0.0245 (6)
H10A0.30510.73580.16830.029*
C11A0.4164 (2)0.66929 (17)0.26810 (15)0.0213 (5)
C12A0.4173 (2)0.63440 (17)0.35689 (15)0.0238 (6)
H12A0.33570.63330.39480.029*
C13A0.5383 (2)0.60111 (17)0.38975 (16)0.0249 (6)
H13A0.53640.57860.44960.030*
C14A0.6620 (2)0.60045 (17)0.33603 (16)0.0242 (6)
C15A0.6609 (2)0.63709 (18)0.24672 (16)0.0268 (6)
H15A0.74290.63880.20890.032*
C16A0.5410 (2)0.67088 (17)0.21306 (16)0.0245 (6)
H16A0.54340.69490.15310.029*
C17A0.7915 (3)0.55792 (19)0.37397 (17)0.0298 (6)
H17A0.78690.56920.42840.036*
H17B0.87030.59430.33430.036*
C18A0.8138 (2)0.44485 (18)0.39067 (15)0.0247 (6)
H18A0.72960.40970.42590.030*
C19A0.9313 (3)0.40483 (19)0.44231 (18)0.0336 (6)
H19A0.93960.33320.45630.050*
H19B0.91260.41970.49500.050*
H19C1.01560.43640.40820.050*
C20A0.8408 (3)0.42227 (19)0.30693 (17)0.0358 (7)
H20A0.85450.35100.32020.054*
H20B0.92170.45730.27070.054*
H20C0.76330.44420.27690.054*
C21A0.8043 (3)0.84942 (18)0.00711 (18)0.0314 (6)
H21A0.87840.8193−0.02140.047*
H21B0.71850.8360−0.00620.047*
H21C0.80280.82140.06890.047*
C22A0.1956 (3)0.6086 (2)0.24750 (18)0.0335 (6)
H22A0.11700.62940.21840.050*
H22B0.16540.57660.30890.050*
H22C0.25040.56200.22530.050*
S1B0.76869 (7)1.16289 (5)0.46186 (4)0.02935 (17)
O1B0.12190 (16)0.86906 (12)0.82309 (10)0.0249 (4)
O2B0.03960 (17)1.04132 (15)0.84371 (11)0.0272 (4)
N1B0.55655 (18)0.96259 (14)0.59078 (12)0.0204 (4)
N2B0.67979 (18)0.96233 (14)0.53497 (12)0.0199 (4)
N3B0.8661 (2)0.98759 (16)0.44571 (13)0.0234 (5)
N4B0.83900 (19)0.88679 (15)0.46948 (12)0.0227 (5)
C1B0.3228 (2)0.94956 (18)0.71665 (14)0.0203 (5)
H1BA0.35100.89090.70560.024*
C2B0.2040 (2)0.95066 (18)0.77424 (14)0.0208 (5)
C3B0.1595 (2)1.04026 (18)0.78779 (14)0.0213 (5)
C4B0.2352 (2)1.12697 (18)0.74649 (14)0.0216 (5)
H4BA0.20441.18650.75540.026*
C5B0.3578 (2)1.12518 (18)0.69152 (14)0.0210 (5)
H5BA0.41151.18280.66560.025*
C6B0.4004 (2)1.03784 (17)0.67511 (14)0.0194 (5)
C7B0.5282 (2)1.03830 (18)0.61510 (14)0.0198 (5)
H7BA0.58771.09280.59510.024*
C8B0.7711 (2)1.03861 (18)0.48228 (14)0.0221 (5)
C9B0.7242 (2)0.87318 (18)0.52375 (14)0.0208 (5)
C10B0.6490 (2)0.77595 (17)0.57006 (15)0.0217 (5)
H10B0.55160.78860.56430.026*
C11B0.6591 (2)0.73653 (17)0.66668 (15)0.0226 (5)
C12B0.7824 (3)0.73933 (19)0.69533 (16)0.0299 (6)
H12B0.86040.76600.65500.036*
C13B0.7903 (3)0.7030 (2)0.78281 (17)0.0342 (6)
H13B0.87380.70610.80030.041*
C14B0.6771 (3)0.66181 (19)0.84572 (16)0.0300 (6)
C15B0.5549 (3)0.6571 (2)0.81633 (17)0.0348 (7)
H15B0.47780.62840.85660.042*
C16B0.5456 (3)0.6942 (2)0.72841 (16)0.0318 (6)
H16B0.46250.69070.71070.038*
C17B0.6842 (3)0.6274 (2)0.94214 (16)0.0355 (7)
H17C0.59720.59620.97410.043*0.785 (6)
H17D0.69320.68670.95670.043*0.785 (6)
H17E0.59450.63550.97250.043*0.215 (6)
H17F0.74580.67090.95100.043*0.215 (6)
C18B0.7994 (5)0.5541 (3)0.9742 (2)0.0301 (10)0.785 (6)
H18B0.88650.58400.93900.036*0.785 (6)
C19B0.7853 (5)0.4535 (3)0.9638 (3)0.0417 (12)0.785 (6)
H19D0.78240.46430.90390.062*0.785 (6)
H19E0.70200.42140.99920.062*0.785 (6)
H19F0.86280.41110.98170.062*0.785 (6)
C20B0.8060 (6)0.5394 (4)1.0684 (2)0.0390 (11)0.785 (6)
H20D0.87940.49321.08770.059*0.785 (6)
H20E0.72020.51261.10420.059*0.785 (6)
H20F0.82250.60301.07280.059*0.785 (6)
C18C0.7281 (19)0.5229 (13)0.9807 (9)0.032 (4)0.215 (6)
H18C0.65390.48160.97890.038*0.215 (6)
C19C0.855 (2)0.4920 (12)0.9330 (10)0.0417 (12)0.215 (6)
H19G0.84220.50270.87460.062*0.215 (6)
H19H0.87410.42190.96210.062*0.215 (6)
H19I0.93130.53150.93140.062*0.215 (6)
C20C0.7302 (17)0.5010 (13)1.0787 (9)0.037 (4)0.215 (6)
H20G0.74330.43001.10770.056*0.215 (6)
H20H0.64430.52221.10450.056*0.215 (6)
H20I0.80430.53731.08450.056*0.215 (6)
C21B0.1587 (3)0.77692 (19)0.80815 (18)0.0338 (6)
H21D0.09480.72530.84540.051*
H21E0.25000.75700.82060.051*
H21F0.15600.78650.74850.051*
C22B0.7028 (3)0.69751 (19)0.52920 (17)0.0308 (6)
H22D0.69110.72210.46920.046*
H22E0.65250.63610.55960.046*
H22F0.79880.68490.53310.046*
H1N30.001 (3)0.837 (2)0.3856 (18)0.040 (9)*
H2N30.938 (3)1.0140 (19)0.4079 (16)0.029 (7)*
H1O20.912 (3)1.111 (2)−0.0781 (19)0.036 (9)*
H2O20.006 (3)0.984 (2)0.8625 (19)0.047 (10)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S1A0.0174 (3)0.0280 (4)0.0254 (3)0.0006 (3)0.0021 (3)−0.0098 (3)
O1A0.0181 (9)0.0224 (9)0.0300 (9)0.0023 (7)0.0054 (7)−0.0103 (8)
O2A0.0225 (10)0.0256 (10)0.0305 (10)−0.0032 (8)0.0067 (8)−0.0081 (9)
N1A0.0126 (10)0.0290 (12)0.0183 (10)−0.0001 (9)−0.0002 (8)−0.0056 (9)
N2A0.0122 (10)0.0237 (11)0.0185 (10)0.0005 (8)−0.0001 (8)−0.0052 (9)
N3A0.0166 (11)0.0283 (12)0.0202 (11)−0.0001 (9)0.0020 (9)−0.0082 (10)
N4A0.0177 (11)0.0279 (12)0.0252 (11)−0.0002 (9)−0.0014 (9)−0.0086 (9)
C1A0.0180 (13)0.0200 (13)0.0196 (12)−0.0012 (10)−0.0044 (10)−0.0042 (10)
C2A0.0155 (12)0.0244 (14)0.0182 (12)0.0041 (10)−0.0033 (10)−0.0070 (10)
C3A0.0165 (12)0.0244 (14)0.0154 (12)−0.0013 (10)−0.0016 (10)−0.0032 (10)
C4A0.0242 (13)0.0199 (13)0.0219 (13)0.0006 (10)−0.0031 (10)−0.0051 (11)
C5A0.0200 (13)0.0282 (14)0.0234 (13)0.0054 (11)−0.0031 (10)−0.0121 (11)
C6A0.0164 (12)0.0251 (14)0.0168 (12)0.0011 (10)−0.0029 (10)−0.0068 (10)
C7A0.0181 (13)0.0256 (15)0.0206 (13)0.0030 (11)−0.0025 (10)−0.0076 (11)
C8A0.0124 (12)0.0291 (14)0.0169 (12)0.0024 (10)−0.0031 (9)−0.0057 (11)
C9A0.0162 (12)0.0293 (15)0.0189 (12)0.0011 (10)−0.0044 (10)−0.0061 (11)
C10A0.0226 (13)0.0274 (14)0.0229 (13)0.0004 (11)−0.0007 (10)−0.0097 (11)
C11A0.0205 (13)0.0176 (13)0.0255 (13)0.0002 (10)−0.0026 (10)−0.0077 (11)
C12A0.0214 (13)0.0222 (13)0.0251 (13)−0.0028 (10)0.0016 (10)−0.0070 (11)
C13A0.0276 (14)0.0207 (13)0.0242 (13)−0.0006 (11)−0.0056 (11)−0.0044 (11)
C14A0.0237 (13)0.0161 (13)0.0332 (15)−0.0005 (10)−0.0043 (11)−0.0091 (11)
C15A0.0197 (13)0.0234 (14)0.0355 (15)0.0002 (11)0.0022 (11)−0.0113 (12)
C16A0.0251 (14)0.0216 (13)0.0235 (13)0.0016 (11)−0.0013 (11)−0.0054 (11)
C17A0.0227 (14)0.0287 (15)0.0391 (16)0.0019 (11)−0.0075 (11)−0.0126 (12)
C18A0.0221 (13)0.0214 (13)0.0270 (14)0.0002 (10)−0.0030 (11)−0.0047 (11)
C19A0.0286 (15)0.0276 (15)0.0407 (16)0.0033 (12)−0.0094 (12)−0.0062 (13)
C20A0.0474 (18)0.0223 (14)0.0339 (16)0.0079 (13)−0.0063 (13)−0.0067 (12)
C21A0.0244 (14)0.0223 (14)0.0457 (17)0.0024 (11)0.0032 (12)−0.0146 (13)
C22A0.0279 (15)0.0364 (16)0.0415 (16)0.0011 (12)−0.0054 (12)−0.0205 (13)
S1B0.0273 (4)0.0275 (4)0.0281 (4)−0.0055 (3)0.0048 (3)−0.0069 (3)
O1B0.0181 (9)0.0238 (9)0.0265 (9)−0.0047 (7)0.0018 (7)−0.0029 (8)
O2B0.0165 (9)0.0348 (12)0.0268 (10)−0.0016 (8)0.0063 (7)−0.0111 (9)
N1B0.0113 (10)0.0276 (12)0.0195 (10)0.0002 (8)0.0012 (8)−0.0066 (9)
N2B0.0137 (10)0.0256 (11)0.0180 (10)−0.0003 (8)0.0002 (8)−0.0060 (9)
N3B0.0136 (11)0.0312 (13)0.0231 (11)−0.0010 (9)0.0028 (9)−0.0091 (10)
N4B0.0170 (11)0.0295 (12)0.0210 (11)0.0023 (9)−0.0023 (8)−0.0090 (9)
C1B0.0176 (12)0.0220 (13)0.0207 (12)0.0026 (10)−0.0024 (10)−0.0075 (11)
C2B0.0157 (12)0.0247 (14)0.0189 (12)−0.0031 (10)−0.0044 (10)−0.0028 (11)
C3B0.0165 (12)0.0291 (14)0.0157 (12)0.0016 (10)−0.0015 (10)−0.0058 (11)
C4B0.0213 (13)0.0238 (14)0.0205 (12)0.0031 (10)−0.0029 (10)−0.0098 (11)
C5B0.0192 (13)0.0226 (13)0.0189 (12)−0.0015 (10)−0.0031 (10)−0.0041 (10)
C6B0.0157 (12)0.0240 (13)0.0159 (12)−0.0002 (10)−0.0033 (9)−0.0036 (10)
C7B0.0159 (12)0.0237 (13)0.0181 (12)0.0003 (10)−0.0030 (10)−0.0054 (11)
C8B0.0147 (12)0.0332 (15)0.0166 (12)−0.0026 (11)−0.0011 (10)−0.0068 (11)
C9B0.0164 (12)0.0277 (14)0.0202 (12)0.0062 (10)−0.0058 (10)−0.0106 (11)
C10B0.0165 (12)0.0245 (14)0.0241 (13)0.0011 (10)−0.0037 (10)−0.0088 (11)
C11B0.0218 (13)0.0182 (13)0.0267 (13)0.0046 (10)−0.0034 (10)−0.0078 (11)
C12B0.0258 (14)0.0330 (15)0.0261 (14)−0.0036 (12)−0.0055 (11)−0.0034 (12)
C13B0.0354 (16)0.0362 (16)0.0307 (15)−0.0044 (13)−0.0133 (12)−0.0070 (13)
C14B0.0360 (16)0.0268 (15)0.0279 (14)0.0054 (12)−0.0042 (12)−0.0120 (12)
C15B0.0288 (15)0.0400 (17)0.0271 (15)0.0015 (12)0.0040 (12)−0.0059 (13)
C16B0.0204 (14)0.0397 (16)0.0315 (15)0.0012 (12)−0.0015 (11)−0.0095 (13)
C17B0.0476 (18)0.0315 (16)0.0265 (14)0.0080 (13)−0.0068 (13)−0.0103 (12)
C18B0.038 (3)0.026 (2)0.025 (2)−0.004 (2)−0.0014 (19)−0.0080 (17)
C19B0.069 (3)0.025 (2)0.031 (2)0.004 (2)−0.007 (2)−0.0104 (19)
C20B0.053 (3)0.036 (3)0.026 (2)0.000 (2)−0.009 (2)−0.0090 (19)
C18C0.030 (9)0.030 (10)0.030 (8)0.007 (7)−0.013 (7)−0.001 (7)
C19C0.069 (3)0.025 (2)0.031 (2)0.004 (2)−0.007 (2)−0.0104 (19)
C20C0.030 (9)0.028 (9)0.036 (8)0.013 (7)−0.008 (7)0.008 (7)
C21B0.0279 (15)0.0279 (15)0.0401 (16)−0.0082 (12)0.0020 (12)−0.0075 (13)
C22B0.0331 (15)0.0316 (15)0.0297 (15)0.0060 (12)−0.0090 (12)−0.0124 (12)

Geometric parameters (Å, °)

S1A—C8A1.680 (2)N1B—N2B1.396 (2)
O1A—C2A1.379 (3)N2B—C9B1.376 (3)
O1A—C21A1.425 (3)N2B—C8B1.392 (3)
O2A—C3A1.366 (3)N3B—C8B1.339 (3)
O2A—H1O20.75 (3)N3B—N4B1.374 (3)
N1A—C7A1.281 (3)N3B—H2N30.87 (3)
N1A—N2A1.405 (2)N4B—C9B1.298 (3)
N2A—C8A1.383 (3)C1B—C2B1.381 (3)
N2A—C9A1.383 (3)C1B—C6B1.402 (3)
N3A—C8A1.337 (3)C1B—H1BA0.9300
N3A—N4A1.379 (3)C2B—C3B1.398 (3)
N3A—H1N30.81 (3)C3B—C4B1.375 (3)
N4A—C9A1.306 (3)C4B—C5B1.388 (3)
C1A—C2A1.375 (3)C4B—H4BA0.9300
C1A—C6A1.403 (3)C5B—C6B1.385 (3)
C1A—H1AA0.9300C5B—H5BA0.9300
C2A—C3A1.403 (3)C6B—C7B1.465 (3)
C3A—C4A1.383 (3)C7B—H7BA0.9300
C4A—C5A1.387 (3)C9B—C10B1.495 (3)
C4A—H4AA0.9300C10B—C22B1.523 (3)
C5A—C6A1.391 (3)C10B—C11B1.524 (3)
C5A—H5AA0.9300C10B—H10B0.9800
C6A—C7A1.458 (3)C11B—C16B1.387 (3)
C7A—H7AA0.9300C11B—C12B1.390 (3)
C9A—C10A1.488 (3)C12B—C13B1.377 (3)
C10A—C11A1.530 (3)C12B—H12B0.9300
C10A—C22A1.530 (3)C13B—C14B1.389 (4)
C10A—H10A0.9800C13B—H13B0.9300
C11A—C12A1.385 (3)C14B—C15B1.393 (4)
C11A—C16A1.396 (3)C14B—C17B1.517 (3)
C12A—C13A1.383 (3)C15B—C16B1.387 (4)
C12A—H12A0.9300C15B—H15B0.9300
C13A—C14A1.383 (3)C16B—H16B0.9300
C13A—H13A0.9300C17B—C18C1.460 (15)
C14A—C15A1.393 (3)C17B—C18B1.520 (5)
C14A—C17A1.516 (3)C17B—H17C0.9700
C15A—C16A1.380 (3)C17B—H17D0.9700
C15A—H15A0.9300C17B—H17E0.9602
C16A—H16A0.9300C17B—H17F0.9599
C17A—C18A1.535 (3)C18B—C19B1.518 (6)
C17A—H17A0.9700C18B—C20B1.521 (5)
C17A—H17B0.9700C18B—H18B0.9800
C18A—C20A1.517 (3)C19B—H19D0.9600
C18A—C19A1.521 (3)C19B—H19E0.9600
C18A—H18A0.9800C19B—H19F0.9600
C19A—H19A0.9600C20B—H20D0.9600
C19A—H19B0.9600C20B—H20E0.9600
C19A—H19C0.9600C20B—H20F0.9600
C20A—H20A0.9600C18C—C19C1.49 (2)
C20A—H20B0.9600C18C—C20C1.55 (2)
C20A—H20C0.9600C18C—H18C0.9800
C21A—H21A0.9600C19C—H19G0.9600
C21A—H21B0.9600C19C—H19H0.9600
C21A—H21C0.9600C19C—H19I0.9600
C22A—H22A0.9600C20C—H20G0.9600
C22A—H22B0.9600C20C—H20H0.9600
C22A—H22C0.9600C20C—H20I0.9600
S1B—C8B1.673 (3)C21B—H21D0.9600
O1B—C2B1.374 (3)C21B—H21E0.9600
O1B—C21B1.428 (3)C21B—H21F0.9600
O2B—C3B1.375 (3)C22B—H22D0.9600
O2B—H2O20.83 (3)C22B—H22E0.9600
N1B—C7B1.276 (3)C22B—H22F0.9600
C2A—O1A—C21A117.01 (17)C2B—C1B—H1BA120.4
C3A—O2A—H1O2104 (2)C6B—C1B—H1BA120.4
C7A—N1A—N2A118.84 (19)O1B—C2B—C1B125.8 (2)
C8A—N2A—C9A108.79 (18)O1B—C2B—C3B114.27 (19)
C8A—N2A—N1A133.50 (19)C1B—C2B—C3B119.9 (2)
C9A—N2A—N1A117.71 (18)O2B—C3B—C4B119.7 (2)
C8A—N3A—N4A114.89 (19)O2B—C3B—C2B119.6 (2)
C8A—N3A—H1N3126 (2)C4B—C3B—C2B120.7 (2)
N4A—N3A—H1N3118 (2)C3B—C4B—C5B119.6 (2)
C9A—N4A—N3A103.57 (19)C3B—C4B—H4BA120.2
C2A—C1A—C6A120.0 (2)C5B—C4B—H4BA120.2
C2A—C1A—H1AA120.0C6B—C5B—C4B120.2 (2)
C6A—C1A—H1AA120.0C6B—C5B—H5BA119.9
C1A—C2A—O1A125.1 (2)C4B—C5B—H5BA119.9
C1A—C2A—C3A120.3 (2)C5B—C6B—C1B120.2 (2)
O1A—C2A—C3A114.67 (19)C5B—C6B—C7B119.3 (2)
O2A—C3A—C4A117.9 (2)C1B—C6B—C7B120.4 (2)
O2A—C3A—C2A122.3 (2)N1B—C7B—C6B118.8 (2)
C4A—C3A—C2A119.8 (2)N1B—C7B—H7BA120.6
C3A—C4A—C5A119.9 (2)C6B—C7B—H7BA120.6
C3A—C4A—H4AA120.0N3B—C8B—N2B101.5 (2)
C5A—C4A—H4AA120.0N3B—C8B—S1B126.27 (18)
C4A—C5A—C6A120.5 (2)N2B—C8B—S1B132.20 (17)
C4A—C5A—H5AA119.7N4B—C9B—N2B110.2 (2)
C6A—C5A—H5AA119.7N4B—C9B—C10B126.5 (2)
C5A—C6A—C1A119.4 (2)N2B—C9B—C10B123.29 (19)
C5A—C6A—C7A118.6 (2)C9B—C10B—C22B110.97 (19)
C1A—C6A—C7A121.9 (2)C9B—C10B—C11B110.98 (19)
N1A—C7A—C6A120.1 (2)C22B—C10B—C11B110.61 (19)
N1A—C7A—H7AA120.0C9B—C10B—H10B108.1
C6A—C7A—H7AA120.0C22B—C10B—H10B108.1
N3A—C8A—N2A102.15 (19)C11B—C10B—H10B108.1
N3A—C8A—S1A127.63 (17)C16B—C11B—C12B118.2 (2)
N2A—C8A—S1A130.20 (18)C16B—C11B—C10B120.5 (2)
N4A—C9A—N2A110.6 (2)C12B—C11B—C10B121.3 (2)
N4A—C9A—C10A125.6 (2)C13B—C12B—C11B120.7 (2)
N2A—C9A—C10A123.8 (2)C13B—C12B—H12B119.6
C9A—C10A—C11A110.58 (19)C11B—C12B—H12B119.6
C9A—C10A—C22A110.9 (2)C12B—C13B—C14B122.0 (2)
C11A—C10A—C22A110.7 (2)C12B—C13B—H13B119.0
C9A—C10A—H10A108.2C14B—C13B—H13B119.0
C11A—C10A—H10A108.2C13B—C14B—C15B116.9 (2)
C22A—C10A—H10A108.2C13B—C14B—C17B121.7 (2)
C12A—C11A—C16A118.0 (2)C15B—C14B—C17B121.3 (2)
C12A—C11A—C10A121.1 (2)C16B—C15B—C14B121.5 (2)
C16A—C11A—C10A120.8 (2)C16B—C15B—H15B119.2
C13A—C12A—C11A120.7 (2)C14B—C15B—H15B119.2
C13A—C12A—H12A119.6C11B—C16B—C15B120.7 (2)
C11A—C12A—H12A119.6C11B—C16B—H16B119.7
C14A—C13A—C12A121.8 (2)C15B—C16B—H16B119.7
C14A—C13A—H13A119.1C18C—C17B—C14B114.9 (6)
C12A—C13A—H13A119.1C18C—C17B—C18B32.2 (7)
C13A—C14A—C15A117.3 (2)C14B—C17B—C18B116.8 (2)
C13A—C14A—C17A120.7 (2)C18C—C17B—H17C79.2
C15A—C14A—C17A122.0 (2)C14B—C17B—H17C108.1
C16A—C15A—C14A121.5 (2)C18B—C17B—H17C108.1
C16A—C15A—H15A119.2C18C—C17B—H17D131.9
C14A—C15A—H15A119.2C14B—C17B—H17D108.1
C15A—C16A—C11A120.6 (2)C18B—C17B—H17D108.1
C15A—C16A—H16A119.7H17C—C17B—H17D107.3
C11A—C16A—H16A119.7C18C—C17B—H17E108.1
C14A—C17A—C18A113.7 (2)C14B—C17B—H17E108.5
C14A—C17A—H17A108.8C18B—C17B—H17E129.5
C18A—C17A—H17A108.8H17C—C17B—H17E33.0
C14A—C17A—H17B108.8H17D—C17B—H17E76.2
C18A—C17A—H17B108.8C18C—C17B—H17F109.2
H17A—C17A—H17B107.7C14B—C17B—H17F108.5
C20A—C18A—C19A110.5 (2)C18B—C17B—H17F78.9
C20A—C18A—C17A112.2 (2)H17C—C17B—H17F133.8
C19A—C18A—C17A110.2 (2)H17D—C17B—H17F33.6
C20A—C18A—H18A108.0H17E—C17B—H17F107.5
C19A—C18A—H18A108.0C19B—C18B—C17B112.3 (4)
C17A—C18A—H18A108.0C19B—C18B—C20B110.8 (3)
C18A—C19A—H19A109.5C17B—C18B—C20B110.4 (3)
C18A—C19A—H19B109.5C19B—C18B—H18B107.7
H19A—C19A—H19B109.5C17B—C18B—H18B107.7
C18A—C19A—H19C109.5C20B—C18B—H18B107.7
H19A—C19A—H19C109.5C17B—C18C—C19C115.6 (14)
H19B—C19A—H19C109.5C17B—C18C—C20C107.9 (11)
C18A—C20A—H20A109.5C19C—C18C—C20C115.0 (12)
C18A—C20A—H20B109.5C17B—C18C—H18C105.8
H20A—C20A—H20B109.5C19C—C18C—H18C105.8
C18A—C20A—H20C109.5C20C—C18C—H18C105.8
H20A—C20A—H20C109.5C18C—C19C—H19G109.5
H20B—C20A—H20C109.5C18C—C19C—H19H109.5
O1A—C21A—H21A109.5H19G—C19C—H19H109.5
O1A—C21A—H21B109.5C18C—C19C—H19I109.5
H21A—C21A—H21B109.5H19G—C19C—H19I109.5
O1A—C21A—H21C109.5H19H—C19C—H19I109.5
H21A—C21A—H21C109.5C18C—C20C—H20G109.5
H21B—C21A—H21C109.5C18C—C20C—H20H109.5
C10A—C22A—H22A109.5H20G—C20C—H20H109.5
C10A—C22A—H22B109.5C18C—C20C—H20I109.5
H22A—C22A—H22B109.5H20G—C20C—H20I109.5
C10A—C22A—H22C109.5H20H—C20C—H20I109.5
H22A—C22A—H22C109.5O1B—C21B—H21D109.5
H22B—C22A—H22C109.5O1B—C21B—H21E109.5
C2B—O1B—C21B116.45 (18)H21D—C21B—H21E109.5
C3B—O2B—H2O2108 (2)O1B—C21B—H21F109.5
C7B—N1B—N2B118.68 (19)H21D—C21B—H21F109.5
C9B—N2B—C8B109.26 (18)H21E—C21B—H21F109.5
C9B—N2B—N1B118.38 (18)C10B—C22B—H22D109.5
C8B—N2B—N1B132.31 (19)C10B—C22B—H22E109.5
C8B—N3B—N4B114.66 (19)H22D—C22B—H22E109.5
C8B—N3B—H2N3125.0 (17)C10B—C22B—H22F109.5
N4B—N3B—H2N3120.3 (17)H22D—C22B—H22F109.5
C9B—N4B—N3B104.41 (18)H22E—C22B—H22F109.5
C2B—C1B—C6B119.3 (2)
C7A—N1A—N2A—C8A−0.3 (3)C21B—O1B—C2B—C3B176.7 (2)
C7A—N1A—N2A—C9A179.9 (2)C6B—C1B—C2B—O1B−176.3 (2)
C8A—N3A—N4A—C9A0.5 (3)C6B—C1B—C2B—C3B2.6 (3)
C6A—C1A—C2A—O1A179.2 (2)O1B—C2B—C3B—O2B−2.5 (3)
C6A—C1A—C2A—C3A−1.0 (3)C1B—C2B—C3B—O2B178.5 (2)
C21A—O1A—C2A—C1A−6.5 (3)O1B—C2B—C3B—C4B176.8 (2)
C21A—O1A—C2A—C3A173.7 (2)C1B—C2B—C3B—C4B−2.2 (3)
C1A—C2A—C3A—O2A179.4 (2)O2B—C3B—C4B—C5B178.6 (2)
O1A—C2A—C3A—O2A−0.7 (3)C2B—C3B—C4B—C5B−0.7 (3)
C1A—C2A—C3A—C4A0.4 (3)C3B—C4B—C5B—C6B3.1 (3)
O1A—C2A—C3A—C4A−179.8 (2)C4B—C5B—C6B—C1B−2.6 (3)
O2A—C3A—C4A—C5A−178.4 (2)C4B—C5B—C6B—C7B178.4 (2)
C2A—C3A—C4A—C5A0.8 (3)C2B—C1B—C6B—C5B−0.3 (3)
C3A—C4A—C5A—C6A−1.2 (3)C2B—C1B—C6B—C7B178.7 (2)
C4A—C5A—C6A—C1A0.6 (3)N2B—N1B—C7B—C6B−178.74 (19)
C4A—C5A—C6A—C7A179.5 (2)C5B—C6B—C7B—N1B−170.1 (2)
C2A—C1A—C6A—C5A0.5 (3)C1B—C6B—C7B—N1B10.9 (3)
C2A—C1A—C6A—C7A−178.3 (2)N4B—N3B—C8B—N2B1.8 (2)
N2A—N1A—C7A—C6A178.74 (19)N4B—N3B—C8B—S1B−175.74 (17)
C5A—C6A—C7A—N1A175.1 (2)C9B—N2B—C8B—N3B−2.0 (2)
C1A—C6A—C7A—N1A−6.1 (3)N1B—N2B—C8B—N3B−179.3 (2)
N4A—N3A—C8A—N2A−0.7 (2)C9B—N2B—C8B—S1B175.30 (19)
N4A—N3A—C8A—S1A177.76 (17)N1B—N2B—C8B—S1B−2.0 (4)
C9A—N2A—C8A—N3A0.6 (2)N3B—N4B—C9B—N2B−0.5 (2)
N1A—N2A—C8A—N3A−179.3 (2)N3B—N4B—C9B—C10B−179.5 (2)
C9A—N2A—C8A—S1A−177.78 (18)C8B—N2B—C9B—N4B1.7 (3)
N1A—N2A—C8A—S1A2.3 (4)N1B—N2B—C9B—N4B179.41 (18)
N3A—N4A—C9A—N2A−0.1 (2)C8B—N2B—C9B—C10B−179.4 (2)
N3A—N4A—C9A—C10A176.8 (2)N1B—N2B—C9B—C10B−1.6 (3)
C8A—N2A—C9A—N4A−0.4 (3)N4B—C9B—C10B—C22B−14.6 (3)
N1A—N2A—C9A—N4A179.54 (18)N2B—C9B—C10B—C22B166.5 (2)
C8A—N2A—C9A—C10A−177.3 (2)N4B—C9B—C10B—C11B108.8 (3)
N1A—N2A—C9A—C10A2.6 (3)N2B—C9B—C10B—C11B−70.0 (3)
N4A—C9A—C10A—C11A−105.8 (3)C9B—C10B—C11B—C16B139.1 (2)
N2A—C9A—C10A—C11A70.7 (3)C22B—C10B—C11B—C16B−97.3 (3)
N4A—C9A—C10A—C22A17.4 (3)C9B—C10B—C11B—C12B−42.7 (3)
N2A—C9A—C10A—C22A−166.1 (2)C22B—C10B—C11B—C12B80.9 (3)
C9A—C10A—C11A—C12A50.2 (3)C16B—C11B—C12B—C13B−1.4 (4)
C22A—C10A—C11A—C12A−73.0 (3)C10B—C11B—C12B—C13B−179.7 (2)
C9A—C10A—C11A—C16A−132.4 (2)C11B—C12B—C13B—C14B0.4 (4)
C22A—C10A—C11A—C16A104.3 (3)C12B—C13B—C14B—C15B1.1 (4)
C16A—C11A—C12A—C13A−0.7 (3)C12B—C13B—C14B—C17B−176.4 (2)
C10A—C11A—C12A—C13A176.7 (2)C13B—C14B—C15B—C16B−1.6 (4)
C11A—C12A—C13A—C14A−0.5 (4)C17B—C14B—C15B—C16B175.9 (2)
C12A—C13A—C14A—C15A1.5 (3)C12B—C11B—C16B—C15B0.9 (4)
C12A—C13A—C14A—C17A−176.4 (2)C10B—C11B—C16B—C15B179.2 (2)
C13A—C14A—C15A—C16A−1.2 (3)C14B—C15B—C16B—C11B0.6 (4)
C17A—C14A—C15A—C16A176.6 (2)C13B—C14B—C17B—C18C−89.0 (9)
C14A—C15A—C16A—C11A0.0 (4)C15B—C14B—C17B—C18C93.6 (9)
C12A—C11A—C16A—C15A1.0 (3)C13B—C14B—C17B—C18B−53.2 (4)
C10A—C11A—C16A—C15A−176.5 (2)C15B—C14B—C17B—C18B129.4 (3)
C13A—C14A—C17A—C18A89.9 (3)C18C—C17B—C18B—C19B30.3 (11)
C15A—C14A—C17A—C18A−87.9 (3)C14B—C17B—C18B—C19B−64.4 (5)
C14A—C17A—C18A—C20A66.0 (3)C18C—C17B—C18B—C20B−93.9 (12)
C14A—C17A—C18A—C19A−170.5 (2)C14B—C17B—C18B—C20B171.4 (3)
C7B—N1B—N2B—C9B166.3 (2)C14B—C17B—C18C—C19C49.4 (18)
C7B—N1B—N2B—C8B−16.6 (3)C18B—C17B—C18C—C19C−51.9 (14)
C8B—N3B—N4B—C9B−0.9 (3)C14B—C17B—C18C—C20C179.7 (9)
C21B—O1B—C2B—C1B−4.4 (3)C18B—C17B—C18C—C20C78.4 (14)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11A—C16A phenyl ring.
D—H···AD—HH···AD···AD—H···A
N3A—H1N3···N4Bi0.82 (3)2.19 (3)2.968 (3)161 (3)
N3B—H2N3···S1Aii0.87 (3)2.39 (3)3.227 (2)161 (3)
O2A—H1O2···O2Biii0.75 (3)2.11 (3)2.808 (3)157 (3)
C7A—H7AA···S1A0.932.433.193 (2)139
C7B—H7BA···S1B0.932.533.243 (2)134
C5B—H5BA···Cg1iv0.932.913.660 (3)139

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2704).

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