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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o2048–o2049.
Published online 2009 July 31. doi:  10.1107/S1600536809029730
PMCID: PMC2977246

1,1′-Dimethyl-4,4′-(2,4-di-1-naphthyl­cyclo­butane-1,3-di­yl)dipyridinium–(E)-1-methyl-4-[2-(1-naphth­yl)vin­yl]pyridinium–4-amino­benzene­sulfonate–water (0.25/1.50/2/2)

Abstract

In the title compound, 1.5C18H16N+·0.25C36H32N2 2+·2C6H6NO3S·2H2O, the monocation exists in the E configuration with respect to the ethenyl C=C double bond and is almost planar, the dihedral angles between the pyridinium and the fused six-membered rings being 3.1 (7) and 3.8 (8)°. The dication lies about an inversion centre. In the crystal, the dication occupies almost the same site occupied by monocations at (x, y, z) and (−x, 1 − y, 1 − z). The anions and water mol­ecules are linked into a chain along the a axis by O—H(...)O and N—H(...)O hydrogen bonds. The structure is further stabilized by C—H(...)O hydrogen bonds and π–π inter­actions between pyridinium and benzene rings, with centroid–centroid distances in the range 3.516 (9)–3.553 (8) Å. The crystal is a twin with twin law, TWIN An external file that holds a picture, illustration, etc.
Object name is e-65-o2048-efi1.jpg 0 0 0 An external file that holds a picture, illustration, etc.
Object name is e-65-o2048-efi1.jpg 0 1 0 1. The monocation and dication are disordered with fractional site occupancy ratio of 0.75:0.25.

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For background to non-linear optical materials, see: Williams (1984 [triangle]). For related structures, see: Chantrapromma et al. (2009 [triangle]); Fun et al. (2009 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2048-scheme1.jpg

Experimental

Crystal data

  • 1.5C18H16N+·0.25C36H32N2 2+·2C6H6NO3S·2H2O
  • M r = 873.04
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2048-efi3.jpg
  • a = 6.6352 (4) Å
  • b = 14.8824 (8) Å
  • c = 20.9347 (13) Å
  • β = 97.921 (3)°
  • V = 2047.5 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.19 mm−1
  • T = 100 K
  • 0.52 × 0.13 × 0.07 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.906, T max = 0.986
  • 21302 measured reflections
  • 4099 independent reflections
  • 3550 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.097
  • wR(F 2) = 0.275
  • S = 1.07
  • 4099 reflections
  • 440 parameters
  • 300 restraints
  • H-atom parameters constrained
  • Δρmax = 1.20 e Å−3
  • Δρmin = −0.62 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/S1600536809029730/ci2847sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029730/ci2847Isup2.hkl

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

Acknowledgments

The authors thank the Prince of Songkla University for financial support through the Crystal Materials Research Unit and the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. KC thanks the Development and Promotion of Science and Technology Talents Project (DPST) for a study grant. Partial financial support from the Graduate School, Prince of Songkla University, is gratefully acknowledged.

supplementary crystallographic information

Comment

The important requirement of NLO material is that the molecules have to align in noncentrosymmetric space group in the crystal (Williams, 1984). So the X-ray structure determination is a very important procedure to find out whether the compound is NLO active. During the course of our NLO research, we have previously reported crystal structures of (E)-1-methyl-4-[2-(2-naphthyl)vinyl]pyridinium iodide (I) (Fun et al., 2009) and (E)-1-methyl-4-[2-(1-naphthyl)vinyl]pyridinium 4-bromobenzenesulfonate (II) (Chantrapromma et al., 2009). These compounds were prepared by extending conjugated π-system which is a popular strategy to design NLO materials. In order to study the relation and effect of anions to the NLO properties, we attempted to synthesize (E)-1-methyl-4-[2-(2-naphthyl)vinyl]pyridinium 4-aminobenzenesulfonate (III) by replacing the iodide anion in (I) by 4-aminobenzenesulfonate. However, we got a co-crystal of the [2+2] cycloaddition product of (E)-1-methyl-4-[2-(2-naphthyl)vinyl]pyridinium with (III). The title compound crystallizes in the monoclinic centrosymmetric space group P21/c, indicating that the second-order NLO properties are not present.

Fig. 1 shows the molecular structure of the title compound, which consists of one and a half C18H16N+ cation, one-quarter of the C36C32N22+ dication, two C6H6NO3S- anions and two water molecules. The monocation exists in the E configuration with respect to the C11═C12 double bond (C10—C11—C12—C13 = -179.9 (10)°) and is almost planar with dihedral angles between the pyridinium and C1–C6 and C1/C6–C10 rings being 3.1 (7) and 3.8 (8)°, respectively. The dication lies on an inversion center. The dihedral angle between the pyridinium and two aromatic C1A–C6A and C1A/C6A–C10A rings being 13 (2) and 14 (2)°, respectively, with the C10A–C11A–C12A–C13A torsion angle being -115 (3)°. Bond lengths are in normal ranges (Allen et al., 1987) and comparable with those in related structures (Chantrapromma et al., 2009; Fun et al., 2009).

In the crystal structure, the anions and water molecules are linked into a chain along the a axis by O—H···O and N—H···O hydrogen bonds (Fig.2). The structure is further stabilized by C—H···O hydrogen bonds (Table 1) and π–π interactions between pyridinium and benzene rings [Cg1···Cg2v = 3.553 (8) Å, Cg1···Cg2vi = 3.530 (8) Å, Cg1···Cg3v = 3.550 (9) Å and Cg1···Cg3vi = 3.516 (9) Å; Cg1, Cg2 and Cg3 are centroids of the N1/C13-C17, C1-C6 and C1/C6-C10 rings, respectively. Symmetry code: (v) -x, 1-y, 1-z; (vi) 1-x, 1-y, 1-z].

Experimental

Silver(I) 4-aminobenzenesulfonate (compound A) was prepared by mixing a solution of sulfanilic acid (0.12 g, 0.71 mmol) in hot methanol (50 ml) with a solution of sodium hydroxide (0.03 g, 0.71 mmol) in methanol (30 ml), followed by addition of a solution of silver nitrate (0.12 g, 0.71 mmol) in methanol (30 ml). A colourless solution together with black solid of AgI was obtained which was then filtered. The white solid of compound A was collected after allowing the filtrate to stand in air for a few days. (E)-1-Methyl-4-[2-(1-naphthyl)vinyl]pyridinium iodide (compound B) was prepared by the previous method (Chantrapromma et al., 2009). The yellow solid of compound B (0.27 g, 0.71 mmol) was mixed with compound A (0.20 g, 0.71 mmol) in methanol (100 ml) and stirred for 30 minutes. The precipitate of silver iodide which formed was filtered and the filtrate was evaporated to give a yellow solid product. The yellow solid was repeatedly recrystallized for three times by dissolving the yellow solid in methanol and the solution was heated at 323 K to get a clear solution. The [2+2] cycloaddition of the (E)-1-methyl-4-[2-(1-naphthyl)vinyl]pyridinium occured upon heating. Green needle-shaped single crystals of the title compound suitable for x-ray structure determination were obtained from a methanol solution by slow evaporation at room temperature over a month (m.p. 513-514 K).

Refinement

The fractional occupancies of the monocation and dication were initially refined to 0.746 (8) and 0.254 (2), respectively, and later for charge-balance they were fixed at 0.75 and 0.25. In the dication, the Uij components of all atoms were restrained to approximate isotropic behaviour and atoms closer than 1.7 Å were restrained to have the same Uij components. Same Uij parameters were used for atoms C2 and C2A and also for C3 and C3A. In the dication, the naphthalene and pyridinium rings were restrained to be planar. All H atoms were positioned geometrically and allowed to ride on their parent atoms, with N-H = 0.86 Å and C-H = 0.93-0.98 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq(C) for the remaining H atoms. The highest residual electron density peak is located at 1.18 Å from C12 and the deepest hole is located at 0.74 Å from S1. The crystal is a twin with twin law, TWIN -1 0 0 0 -1 0 1 0 1 and BASF = 0.036 (1).

Figures

Fig. 1.
The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme. The dication is shown in open bonds. Unlabelled atoms in the dication are related to the labelled atoms by the symmetry operation ...
Fig. 2.
The crystal packing of the title compound viewed down the b axis. Hydrogen bonds are shown as dashed lines. The monocation with a fractional occupancy of 0.75 is shown while the dication with an occupancy of 0.25 has been omitted for clarity.

Crystal data

1.5C18H16N+·0.25C36H32N22+·2C6H6NO3S·2H2OF(000) = 920
Mr = 873.04Dx = 1.416 Mg m3
Monoclinic, P21/cMelting point = 513–514 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.6352 (4) ÅCell parameters from 4099 reflections
b = 14.8824 (8) Åθ = 1.0–26.0°
c = 20.9347 (13) ŵ = 0.19 mm1
β = 97.921 (3)°T = 100 K
V = 2047.5 (2) Å3Needle, green
Z = 20.52 × 0.13 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer4099 independent reflections
Radiation source: sealed tube3550 reflections with I > 2σ(I)
graphiteRint = 0.044
[var phi] and ω scansθmax = 26.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −8→8
Tmin = 0.906, Tmax = 0.986k = −16→18
21302 measured reflectionsl = −25→23

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)] = 0.097Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.275H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.1017P)2 + 16.5792P] where P = (Fo2 + 2Fc2)/3
4099 reflections(Δ/σ)max = 0.001
440 parametersΔρmax = 1.20 e Å3
300 restraintsΔρmin = −0.61 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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)
S10.3679 (2)0.09002 (8)0.28289 (6)0.0218 (3)
O10.5862 (6)0.0903 (2)0.28680 (19)0.0275 (9)
O20.2700 (6)0.0497 (3)0.2232 (2)0.0298 (9)
O30.2958 (7)0.0516 (3)0.3399 (2)0.0352 (10)
N20.1545 (7)0.4776 (3)0.2898 (2)0.0245 (10)
H2B0.24000.51740.28070.029*
H2C0.04260.49400.30280.029*
C190.2965 (8)0.2043 (3)0.2812 (2)0.0197 (10)
C200.4260 (8)0.2701 (4)0.2610 (2)0.0227 (11)
H200.54610.25290.24610.027*
C210.3758 (8)0.3600 (4)0.2630 (3)0.0226 (11)
H210.46420.40280.25010.027*
C220.1966 (8)0.3877 (3)0.2838 (2)0.0197 (10)
C230.0644 (8)0.3219 (4)0.3019 (2)0.0212 (11)
H23−0.05850.33930.31480.025*
C240.1135 (8)0.2316 (4)0.3009 (2)0.0224 (11)
H240.02420.18890.31340.027*
N10.2543 (17)0.1774 (6)0.5190 (5)0.024 (2)0.75
C10.2403 (16)0.6807 (6)0.4633 (4)0.0197 (19)0.75
C20.2154 (18)0.6500 (6)0.3985 (4)0.0223 (17)0.75
H20.21240.58660.39000.027*0.75
C30.1902 (17)0.7092 (5)0.3482 (5)0.0228 (19)0.75
H30.17500.68670.30480.027*0.75
C40.191 (2)0.8026 (7)0.3597 (5)0.025 (3)0.75
H40.17210.84370.32400.030*0.75
C50.215 (3)0.8344 (7)0.4214 (6)0.028 (3)0.75
H50.21770.89800.42900.033*0.75
C60.240 (3)0.7748 (6)0.4755 (5)0.022 (2)0.75
C70.264 (4)0.8077 (7)0.5393 (6)0.025 (3)0.75
H70.25700.87120.54680.030*0.75
C80.294 (3)0.7491 (7)0.5904 (5)0.021 (2)0.75
H80.31590.77140.63380.026*0.75
C90.294 (2)0.6548 (7)0.5788 (4)0.020 (2)0.75
H90.30970.61440.61490.024*0.75
C100.269 (2)0.6203 (6)0.5185 (4)0.025 (2)0.75
C110.2690 (12)0.5210 (5)0.5082 (4)0.0316 (18)0.75
H110.26900.50060.46470.038*0.75
C120.2670 (11)0.4559 (5)0.5546 (4)0.0280 (16)0.75
H120.26510.47450.59840.034*0.75
C130.2678 (15)0.3597 (6)0.5405 (4)0.032 (2)0.75
C140.2476 (19)0.3249 (8)0.4777 (5)0.027 (3)0.75
H140.24190.36470.44140.032*0.75
C150.239 (3)0.2339 (7)0.4682 (6)0.026 (3)0.75
H150.21900.21030.42510.031*0.75
C160.274 (2)0.2081 (7)0.5799 (5)0.028 (3)0.75
H160.28160.16660.61530.034*0.75
C170.2813 (15)0.2983 (7)0.5916 (4)0.025 (2)0.75
H170.29450.31970.63520.030*0.75
C180.259 (2)0.0794 (7)0.5068 (6)0.035 (3)0.75
H18A0.18410.06650.46520.053*0.75
H18B0.19840.04820.53950.053*0.75
H18C0.39740.06020.50780.053*0.75
N1A0.285 (6)0.1907 (16)0.5264 (14)0.018 (5)0.25
C1A0.239 (4)0.6868 (16)0.4553 (14)0.024 (4)0.25
C2A0.208 (6)0.6680 (19)0.3881 (14)0.0223 (17)0.25
H2A0.19850.60860.37420.027*0.25
C3A0.193 (5)0.735 (2)0.3437 (15)0.0228 (19)0.25
H3A0.17320.72090.30000.027*0.25
C4A0.206 (7)0.826 (2)0.3629 (17)0.024 (5)0.25
H4A0.19590.87100.33200.028*0.25
C5A0.233 (10)0.8472 (19)0.4267 (17)0.023 (6)0.25
H5A0.23860.90730.43900.028*0.25
C6A0.254 (11)0.7784 (17)0.4752 (15)0.025 (5)0.25
C7A0.285 (12)0.801 (2)0.5412 (16)0.025 (6)0.25
H7A0.29400.86130.55380.030*0.25
C8A0.300 (10)0.734 (2)0.5867 (16)0.026 (6)0.25
H8A0.31740.74910.63030.031*0.25
C9A0.290 (8)0.643 (2)0.5675 (15)0.026 (6)0.25
H9A0.31360.59840.59900.031*0.25
C10A0.248 (7)0.6176 (16)0.5052 (15)0.025 (5)0.25
C11A0.138 (4)0.5304 (12)0.4899 (10)0.026 (4)0.25
H11A0.20280.50090.45610.031*0.25
C12A0.108 (3)0.4637 (11)0.5361 (9)0.023 (3)0.25
H12A0.13630.48860.57970.028*0.25
C13A0.204 (4)0.3737 (12)0.5336 (10)0.014 (4)0.25
C14A0.208 (5)0.3306 (17)0.4740 (11)0.012 (5)0.25
H14A0.18310.36340.43590.015*0.25
C15A0.247 (8)0.2405 (17)0.4719 (14)0.016 (6)0.25
H15A0.24810.21280.43220.019*0.25
C16A0.284 (6)0.2299 (17)0.5844 (13)0.012 (5)0.25
H16A0.31060.19560.62180.014*0.25
C17A0.244 (4)0.3190 (16)0.5887 (11)0.011 (5)0.25
H17A0.24230.34460.62920.014*0.25
C18A0.300 (6)0.0916 (17)0.5214 (19)0.033 (8)0.25
H18D0.32780.06610.56390.049*0.25
H18E0.40900.07660.49740.049*0.25
H18F0.17470.06800.49980.049*0.25
O1W−0.0921 (7)0.0188 (3)0.3769 (2)0.0447 (12)
H1W10.00980.03200.35900.067*
H2W1−0.19960.03100.35250.067*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0227 (7)0.0165 (6)0.0267 (7)0.0017 (5)0.0054 (5)0.0013 (5)
O10.034 (2)0.0158 (18)0.032 (2)0.0041 (16)0.0041 (17)−0.0007 (16)
O20.031 (2)0.022 (2)0.035 (2)−0.0017 (16)0.0011 (17)−0.0079 (17)
O30.049 (3)0.025 (2)0.034 (2)0.0064 (18)0.015 (2)0.0102 (18)
N20.028 (2)0.014 (2)0.033 (2)0.0018 (18)0.008 (2)−0.0024 (18)
C190.019 (2)0.021 (3)0.018 (2)0.000 (2)0.0002 (19)0.001 (2)
C200.021 (3)0.026 (3)0.022 (3)0.001 (2)0.006 (2)0.001 (2)
C210.022 (3)0.021 (3)0.025 (3)−0.003 (2)0.003 (2)0.005 (2)
C220.030 (3)0.018 (2)0.010 (2)0.001 (2)−0.0016 (19)0.0020 (18)
C230.021 (3)0.024 (3)0.020 (2)0.003 (2)0.007 (2)0.000 (2)
C240.022 (3)0.027 (3)0.019 (2)−0.001 (2)0.002 (2)0.000 (2)
N10.019 (5)0.024 (4)0.027 (4)−0.009 (3)0.001 (3)−0.002 (3)
C10.014 (3)0.025 (4)0.020 (4)−0.003 (3)0.003 (3)−0.007 (3)
C20.020 (3)0.024 (4)0.023 (4)0.001 (3)0.003 (3)−0.002 (3)
C30.023 (3)0.027 (5)0.019 (3)−0.003 (4)0.002 (2)−0.001 (4)
C40.021 (5)0.032 (7)0.021 (4)0.000 (5)−0.002 (3)0.001 (4)
C50.029 (6)0.025 (5)0.028 (5)0.001 (5)0.000 (4)−0.004 (4)
C60.014 (5)0.027 (4)0.027 (4)0.002 (3)0.002 (3)−0.004 (3)
C70.029 (8)0.016 (4)0.029 (5)0.001 (4)0.004 (4)−0.004 (3)
C80.020 (4)0.016 (5)0.026 (4)0.000 (4)−0.001 (3)−0.010 (3)
C90.022 (4)0.022 (5)0.019 (4)0.002 (3)0.007 (4)−0.007 (3)
C100.027 (5)0.026 (4)0.022 (6)−0.003 (3)0.006 (4)−0.008 (3)
C110.029 (4)0.040 (5)0.024 (4)0.008 (3)−0.004 (3)−0.004 (3)
C120.020 (4)0.041 (4)0.023 (4)0.002 (3)0.000 (3)0.000 (3)
C130.034 (5)0.031 (5)0.027 (5)0.015 (4)−0.010 (4)−0.001 (4)
C140.026 (7)0.032 (5)0.022 (4)0.006 (4)0.000 (4)0.001 (4)
C150.020 (5)0.033 (5)0.023 (5)−0.004 (4)0.002 (4)−0.005 (4)
C160.021 (5)0.033 (6)0.030 (5)−0.004 (5)0.005 (4)0.002 (4)
C170.021 (5)0.034 (7)0.019 (4)0.012 (4)−0.001 (3)0.001 (4)
C180.044 (7)0.026 (5)0.034 (6)−0.007 (4)−0.002 (5)−0.002 (4)
N1A0.018 (7)0.017 (7)0.020 (7)−0.003 (6)0.001 (5)0.000 (5)
C1A0.023 (6)0.026 (6)0.024 (6)0.001 (5)0.004 (5)0.001 (5)
C2A0.020 (3)0.024 (4)0.023 (4)0.001 (3)0.003 (3)−0.002 (3)
C3A0.023 (3)0.027 (5)0.019 (3)−0.003 (4)0.002 (2)−0.001 (4)
C4A0.022 (7)0.026 (7)0.022 (7)−0.001 (6)0.002 (5)0.001 (6)
C5A0.023 (7)0.027 (8)0.019 (8)0.000 (6)0.003 (6)−0.001 (6)
C6A0.024 (7)0.026 (7)0.024 (7)0.001 (6)0.004 (6)0.000 (6)
C7A0.026 (8)0.025 (8)0.025 (8)0.000 (6)0.004 (6)0.000 (6)
C8A0.024 (8)0.026 (8)0.028 (8)−0.001 (6)0.004 (6)0.002 (6)
C9A0.025 (8)0.026 (8)0.026 (8)−0.002 (6)0.004 (6)0.002 (6)
C10A0.025 (6)0.029 (7)0.023 (6)−0.002 (5)0.004 (5)−0.003 (5)
C11A0.026 (6)0.027 (6)0.025 (6)−0.001 (5)0.003 (5)−0.001 (5)
C12A0.025 (6)0.025 (6)0.021 (6)0.002 (5)0.005 (5)0.001 (5)
C13A0.016 (6)0.013 (6)0.014 (6)0.002 (5)0.005 (5)0.006 (5)
C14A0.012 (7)0.012 (7)0.013 (7)−0.003 (5)0.004 (5)0.003 (6)
C15A0.015 (8)0.017 (8)0.016 (8)−0.003 (6)0.001 (6)0.002 (6)
C16A0.010 (7)0.014 (8)0.012 (7)0.002 (6)0.003 (5)0.004 (5)
C17A0.012 (7)0.010 (7)0.012 (7)0.004 (6)0.001 (5)0.004 (5)
C18A0.031 (11)0.033 (11)0.034 (11)−0.010 (8)0.006 (8)−0.007 (8)
O1W0.041 (3)0.061 (3)0.034 (2)0.017 (2)0.012 (2)0.015 (2)

Geometric parameters (Å, °)

S1—O11.439 (4)C16—C171.363 (12)
S1—O21.456 (4)C16—H160.96
S1—O31.462 (4)C17—H170.96
S1—C191.765 (5)C18—H18A0.96
N2—C221.376 (7)C18—H18B0.96
N2—H2B0.86C18—H18C0.96
N2—H2C0.86N1A—C16A1.348 (17)
C19—C241.395 (7)N1A—C15A1.354 (16)
C19—C201.406 (7)N1A—C18A1.484 (18)
C20—C211.381 (8)C1A—C2A1.421 (16)
C20—H200.93C1A—C6A1.425 (16)
C21—C221.385 (8)C1A—C10A1.463 (17)
C21—H210.93C2A—C3A1.358 (18)
C22—C231.401 (7)C2A—H2A0.93
C23—C241.384 (8)C3A—C4A1.407 (19)
C23—H230.93C3A—H3A0.93
C24—H240.93C4A—C5A1.361 (18)
N1—C161.344 (10)C4A—H4A0.93
N1—C151.350 (9)C5A—C6A1.435 (16)
N1—C181.481 (11)C5A—H5A0.93
C1—C21.419 (9)C6A—C7A1.411 (16)
C1—C61.423 (9)C7A—C8A1.373 (17)
C1—C101.457 (10)C7A—H7A0.93
C2—C31.364 (10)C8A—C9A1.422 (18)
C2—H20.96C8A—H8A0.93
C3—C41.411 (11)C9A—C10A1.348 (18)
C3—H30.96C9A—H9A0.93
C4—C51.364 (10)C10A—C11A1.500 (9)
C4—H40.96C11A—C12A1.421 (18)
C5—C61.431 (9)C11A—C12Ai1.65 (3)
C5—H50.96C11A—H11A0.98
C6—C71.411 (9)C12A—C13A1.488 (18)
C7—C81.373 (10)C12A—C11Ai1.65 (3)
C7—H70.96C12A—H12A0.98
C8—C91.424 (10)C13A—C17A1.406 (18)
C8—H80.96C13A—C14A1.407 (16)
C9—C101.351 (10)C14A—C15A1.368 (17)
C9—H90.96C14A—H14A0.93
C10—C111.493 (11)C15A—H15A0.93
C11—C121.374 (11)C16A—C17A1.359 (19)
C11—H110.96C16A—H16A0.93
C12—C131.462 (11)C17A—H17A0.93
C12—H120.96C18A—H18D0.96
C13—C171.401 (11)C18A—H18E0.96
C13—C141.402 (10)C18A—H18F0.96
C14—C151.368 (10)O1W—H1W10.84
C14—H140.96O1W—H2W10.84
C15—H150.96
O1—S1—O2112.1 (2)C17—C16—H16119.9
O1—S1—O3113.2 (3)C16—C17—C13120.6 (8)
O2—S1—O3112.5 (3)C16—C17—H17119.6
O1—S1—C19105.2 (2)C13—C17—H17119.8
O2—S1—C19107.1 (2)N1—C18—H18A109.5
O3—S1—C19106.0 (2)N1—C18—H18B109.5
C22—N2—H2B120.0H18A—C18—H18B109.5
C22—N2—H2C120.0N1—C18—H18C109.5
H2B—N2—H2C120.0H18A—C18—H18C109.5
C24—C19—C20118.6 (5)H18B—C18—H18C109.5
C24—C19—S1121.1 (4)C16A—N1A—C15A120.0 (18)
C20—C19—S1120.2 (4)C16A—N1A—C18A120 (2)
C21—C20—C19120.4 (5)C15A—N1A—C18A119.4 (19)
C21—C20—H20119.8C2A—C1A—C6A118.2 (16)
C19—C20—H20119.8C2A—C1A—C10A123.7 (18)
C20—C21—C22121.3 (5)C6A—C1A—C10A118.0 (16)
C20—C21—H21119.4C3A—C2A—C1A121.3 (19)
C22—C21—H21119.4C3A—C2A—H2A119.4
N2—C22—C21120.8 (5)C1A—C2A—H2A119.4
N2—C22—C23120.8 (5)C2A—C3A—C4A120.9 (19)
C21—C22—C23118.3 (5)C2A—C3A—H3A119.5
C24—C23—C22121.2 (5)C4A—C3A—H3A119.5
C24—C23—H23119.4C5A—C4A—C3A120 (2)
C22—C23—H23119.4C5A—C4A—H4A120.0
C23—C24—C19120.2 (5)C3A—C4A—H4A120.0
C23—C24—H24119.9C4A—C5A—C6A121 (2)
C19—C24—H24119.9C4A—C5A—H5A119.5
C16—N1—C15121.5 (8)C6A—C5A—H5A119.5
C16—N1—C18119.8 (8)C7A—C6A—C1A120.8 (17)
C15—N1—C18118.6 (8)C7A—C6A—C5A120.5 (18)
C2—C1—C6119.1 (7)C1A—C6A—C5A118.6 (16)
C2—C1—C10123.1 (7)C8A—C7A—C6A119.4 (19)
C6—C1—C10117.8 (7)C8A—C7A—H7A120.3
C3—C2—C1121.0 (7)C6A—C7A—H7A120.3
C3—C2—H2119.7C7A—C8A—C9A120 (2)
C1—C2—H2119.3C7A—C8A—H8A119.9
C2—C3—C4120.5 (7)C9A—C8A—H8A119.9
C2—C3—H3119.4C10A—C9A—C8A122 (2)
C4—C3—H3120.1C10A—C9A—H9A118.8
C5—C4—C3120.1 (8)C8A—C9A—H9A118.8
C5—C4—H4120.0C9A—C10A—C1A118.6 (17)
C3—C4—H4119.9C9A—C10A—C11A118 (2)
C4—C5—C6121.3 (8)C1A—C10A—C11A119.0 (18)
C4—C5—H5119.8C12A—C11A—C10A124.7 (17)
C6—C5—H5118.9C12A—C11A—C12Ai91.9 (16)
C7—C6—C1120.6 (7)C10A—C11A—C12Ai117 (2)
C7—C6—C5121.3 (8)C12A—C11A—H11A107.2
C1—C6—C5118.1 (7)C10A—C11A—H11A107.2
C8—C7—C6120.1 (7)C12Ai—C11A—H11A107.2
C8—C7—H7120.1C11A—C12A—C13A120.2 (16)
C6—C7—H7119.7C11A—C12A—C11Ai88.1 (16)
C7—C8—C9119.8 (7)C13A—C12A—C11Ai116.5 (17)
C7—C8—H8120.3C11A—C12A—H12A110.1
C9—C8—H8119.9C13A—C12A—H12A110.1
C10—C9—C8122.0 (7)C11Ai—C12A—H12A110.1
C10—C9—H9118.9C17A—C13A—C14A116.1 (16)
C8—C9—H9119.1C17A—C13A—C12A121.7 (16)
C9—C10—C1119.6 (7)C14A—C13A—C12A120.1 (16)
C9—C10—C11120.6 (7)C15A—C14A—C13A120.1 (18)
C1—C10—C11119.9 (7)C15A—C14A—H14A120.0
C12—C11—C10126.6 (7)C13A—C14A—H14A120.0
C12—C11—H11116.6N1A—C15A—C14A121.6 (19)
C10—C11—H11116.8N1A—C15A—H15A119.2
C11—C12—C13123.2 (7)C14A—C15A—H15A119.2
C11—C12—H12118.3N1A—C16A—C17A120.4 (19)
C13—C12—H12118.5N1A—C16A—H16A119.8
C17—C13—C14117.6 (8)C17A—C16A—H16A119.8
C17—C13—C12119.1 (8)C16A—C17A—C13A121.9 (18)
C14—C13—C12123.3 (8)C16A—C17A—H17A119.1
C15—C14—C13119.9 (9)C13A—C17A—H17A119.1
C15—C14—H14120.0N1A—C18A—H18D109.5
C13—C14—H14120.0N1A—C18A—H18E109.5
N1—C15—C14120.4 (9)H18D—C18A—H18E109.5
N1—C15—H15119.8N1A—C18A—H18F109.5
C14—C15—H15119.8H18D—C18A—H18F109.5
N1—C16—C17120.1 (8)H18E—C18A—H18F109.5
N1—C16—H16120.1H1W1—O1W—H2W1110.2
O1—S1—C19—C24−156.2 (4)C18—N1—C16—C17176.2 (12)
O2—S1—C19—C2484.3 (5)N1—C16—C17—C130.3 (16)
O3—S1—C19—C24−36.0 (5)C14—C13—C17—C16−0.3 (15)
O1—S1—C19—C2022.6 (5)C12—C13—C17—C16177.2 (11)
O2—S1—C19—C20−96.9 (4)C6A—C1A—C2A—C3A0(3)
O3—S1—C19—C20142.9 (4)C10A—C1A—C2A—C3A177 (2)
C24—C19—C20—C212.4 (8)C1A—C2A—C3A—C4A0(2)
S1—C19—C20—C21−176.4 (4)C2A—C3A—C4A—C5A0(5)
C19—C20—C21—C22−1.1 (8)C3A—C4A—C5A—C6A2(7)
C20—C21—C22—N2175.5 (5)C2A—C1A—C6A—C7A180 (4)
C20—C21—C22—C23−1.0 (8)C10A—C1A—C6A—C7A2(6)
N2—C22—C23—C24−174.7 (5)C2A—C1A—C6A—C5A1(6)
C21—C22—C23—C241.8 (7)C10A—C1A—C6A—C5A−176 (4)
C22—C23—C24—C19−0.5 (8)C4A—C5A—C6A—C7A179 (5)
C20—C19—C24—C23−1.7 (7)C4A—C5A—C6A—C1A−2(7)
S1—C19—C24—C23177.2 (4)C1A—C6A—C7A—C8A0(8)
C6—C1—C2—C3−0.4 (13)C5A—C6A—C7A—C8A179 (5)
C10—C1—C2—C3−179.7 (9)C6A—C7A—C8A—C9A1(8)
C1—C2—C3—C40.9 (12)C7A—C8A—C9A—C10A−6(7)
C2—C3—C4—C5−0.9 (17)C8A—C9A—C10A—C1A8(6)
C3—C4—C5—C60(2)C8A—C9A—C10A—C11A−149 (4)
C2—C1—C6—C7179.9 (13)C2A—C1A—C10A—C9A176 (3)
C10—C1—C6—C7−1(2)C6A—C1A—C10A—C9A−6(5)
C2—C1—C6—C5−0.1 (19)C2A—C1A—C10A—C11A−27 (4)
C10—C1—C6—C5179.3 (13)C6A—C1A—C10A—C11A151 (4)
C4—C5—C6—C7−179.9 (16)C9A—C10A—C11A—C12A−12 (5)
C4—C5—C6—C10(2)C1A—C10A—C11A—C12A−170 (2)
C1—C6—C7—C82(2)C9A—C10A—C11A—C12Ai101 (4)
C5—C6—C7—C8−178.0 (16)C1A—C10A—C11A—C12Ai−56 (4)
C6—C7—C8—C9−2(2)C10A—C11A—C12A—C13A−115 (3)
C7—C8—C9—C101(2)C12Ai—C11A—C12A—C13A120 (2)
C8—C9—C10—C1−0.1 (19)C10A—C11A—C12A—C11Ai125 (3)
C8—C9—C10—C11−179.9 (13)C12Ai—C11A—C12A—C11Ai0.000 (2)
C2—C1—C10—C9179.2 (10)C11A—C12A—C13A—C17A156 (2)
C6—C1—C10—C9−0.2 (17)C11Ai—C12A—C13A—C17A−100 (2)
C2—C1—C10—C11−1.0 (15)C11A—C12A—C13A—C14A−41 (3)
C6—C1—C10—C11179.7 (13)C11Ai—C12A—C13A—C14A63 (2)
C9—C10—C11—C129.0 (18)C17A—C13A—C14A—C15A0.4 (19)
C1—C10—C11—C12−170.9 (9)C12A—C13A—C14A—C15A−163 (3)
C10—C11—C12—C13−179.9 (10)C16A—N1A—C15A—C14A0(3)
C11—C12—C13—C17175.2 (8)C18A—N1A—C15A—C14A172 (4)
C11—C12—C13—C14−7.4 (14)C13A—C14A—C15A—N1A−1(3)
C17—C13—C14—C150.9 (15)C15A—N1A—C16A—C17A0(3)
C12—C13—C14—C15−176.6 (12)C18A—N1A—C16A—C17A−172 (4)
C16—N1—C15—C141.4 (18)N1A—C16A—C17A—C13A−1(4)
C18—N1—C15—C14−175.7 (13)C14A—C13A—C17A—C16A0(3)
C13—C14—C15—N1−1.4 (18)C12A—C13A—C17A—C16A164 (3)
C15—N1—C16—C17−0.9 (16)

Symmetry codes: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O30.842.012.831 (7)164
O1W—H2W1···O1ii0.842.042.853 (6)164
N2—H2B···O1iii0.862.233.018 (6)153
N2—H2C···O2iv0.862.232.991 (6)147
C18—H18A···O1W0.962.523.448 (13)163
C18—H18B···O1Wv0.962.213.168 (13)173

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2847).

References

  • 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.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chantrapromma, S., Chanawanno, K. & Fun, H.-K. (2009). Acta Cryst. E65, o1144–o1145. [PMC free article] [PubMed]
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.
  • Fun, H. K., Chanawanno, K. & Chantrapromma, S. (2009). Acta Cryst. E65, o1406–o1407. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Williams, D. J. (1984). Angew. Chem. Int. Ed. Engl.23, 690–703.

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