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The crystal structure of the dipolar chromophoric title compound, C20H20N3+·PF6-, is described. The phenyl­ene and pyridyl rings are almost coplanar [dihedral angle 7.5 (2)°], but the phenyl substituent forms a dihedral angle of 56.6 (1)° with the pyridyl ring. The compound crystallizes in the non-centrosymmetric space group Cc and is a likely candidate for the display of quadratic non-linear optical effects.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100012543/sx1113sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100012543/sx1113Isup2.hkl
Contains datablock I

CCDC reference: 156175

Comment top

The discovery of new molecular materials possessing nonlinear optical (NLO) properties is crucial for the development of future optoelectronic and photonic devices (Bosshard et al., 1995; Chemla & Zyss, 1987; Nalwa & Miyata, 1997). It is well established that the creation of efficient quadratic NLO materials requires the optimization of both molecular and bulk properties. The majority of promising candidates consist of dipolar donor-π-acceptor (D-π-A) molecules which must exist in a noncentrosymmetric macroscopic arrangement if quadratic NLO effects, such as frequency doubling (second harmonic generation, SHG), are to be observed.

Although NLO organics are usually neutral molecules, various charged compounds also exhibit NLO behaviour. Hemicyanine dyes, such as the p-toluenesulfonate salt of trans-4'-(dimethylamino)-N-methyl-4-stilbazolium (DAST), are particularly attractive for quadratic NLO applications (Marder et al., 1989, 1994). The NLO properties of related Schiff base chromophores such as trans-4-[4-(dimethylamino)phenyliminomethyl]-N-methylpyridinium have also been studied (Coradin et al., 1996). We have recently found that the molecular quadratic NLO responses of N-arylstilbazolium chromophores are larger than those of their N-methyl counterparts (Coe et al., 2000). Hence, dipolar N-arylpyridinium Schiff base derivatives are also of interest as potential novel NLO materials. The title compound, (I), was synthesized by a base-catalyzed condensation reaction of N-phenylpicolinium chloride hydrate (prepared from the reaction of picoline with 2,4-dinitrochlorobenzene, followed by treatment with aniline, according to a procedure previously published by Coe et al., 1998) with N,N'-dimethyl-4-nitrosoaniline and its structure is presented here. \sch

The cation in (I) is a D-π-A molecule and shows an intense visible absorption band at λmax = 534 nm in acetonitrile. By comparison with existing related molecules, this band is ascribed to a π π* intramolecular charge transfer (ICT) from the highest occupied molecular orbital (primarily localized on the electron-rich NMe2 group) to the lowest unoccupied molecular orbital localized on the electron-deficient pyridinium unit. Such low energy ICT bands are typically associated with large molecular quadratic NLO responses (Bosshard et al., 1995; Chemla & Zyss, 1987; Nalwa & Miyata, 1997). The ICT band in (I) is red-shifted by ca 0.14 eV, but is roughly half as intense, when compared with the corresponding absorption in trans-4'-(dimethylamino)-N-phenyl-4-stilbazolium hexafluorophosphate (Coe et al., 2000; data in acetonitrile).

The molecular structure of the cation in (I) is as indicated by 1NMR spectroscopy, with the phenylene and pyridyl rings adopting the expected trans disposition about the iminomethyl group. The small dihedral angle of 7.5 (2)° defined by these ring planes (C13/C14/C15/C16/C17/C18 and N1/C7/C8/C9/C10/C11) is consistent with substantial π-electronic coupling through the D-π-A framework. The phenyl substituent is twisted with respect to the pyridyl ring, with a dihedral angle of 56.6 (1)° between the planes N1/C7/C8/C9/C10/C11 and C1/C2/C3/C4/C5/C6. As expected, the dipolar cation in (I) shows some evidence for polarization in the ground state, both the pyridyl and phenylene rings being partially quinoidal. For example, the average of the distances C14—C15 and C17—C18 is ca 0.03 Å less than the average of the other phenylene C—C distances. Also, N3—C16 shows appreciable double-bond character, being ca 0.08 Å shorter than N1—C1.

To the best of our knowledge, no crystallographic studies of purely organic compounds closely related to (I) have been reported previously. The only structures containing 4-[(4-R-phenyl)iminomethyl]-N—R'-pyridinium fragments (R and R' are any substituent) are cluster complexes of Rh (Lahoz et al., 1991) or Os (Wong et al., 1995, 1996). The geometric parameters of the diaryl Schiff base unit in (I) are similar to those found in [Os3(µ-H)2(CO)93-CNC5H4CH=NC6H4-4-OC16H33-n)] (Wong et al., 1996).

The crystal packing structure of (I) is of primary importance in relation to quadratic NLO properties. The well studied compound DAST crystallizes in the noncentrosymmetric space group Cc and is highly SHG active (Marder et al., 1989). Although the presence of p-toluenesulfonate anions generally appears to encourage stilbazolium salts to adopt packing motifs favourable for quadratic NLO effects (Marder et al., 1994), the PF6 salt (I) also crystallizes in Cc.

The pseudoplanar trans-4-[4-(dimethylamino)phenyliminomethyl]-pyridinium portions of the cations of (I) align head-to-tail and stack in an essentially parallel fashion, forming polar sheets within a macroscopically polar structure. The plane of the pyridinium ring (N1/C7/C8/C9/C10/C11) in a given molecule and the phenylene ring plane (C13/C14/C15/C16/C17/C18) in the adjacent molecule generated by the symmetry operation (x, 1 − y, z + 1/2) form an angle of 1.5° with an interplanar separation of 3.29 Å, suggestive of π-stacking interactions. The PF6 anions lie in between the cationic sheets and are located close to the electron-deficient pyridinium moieties. The shortest intermolecular contact involving the PF6 anion is C9—H···F3(x, y + 1, z − 1), with H···F1 = 2.43 Å [not H···F3(x, y + 1, z − 1)?]. The anions are arranged in channels which run parallel to the c axis. Similar packing structures have been observed in DAST and related compounds, in which it has been suggested that the intervening anions act to reduce dipole-dipole interactions which would otherwise cause the polar cationic sheets to align antiparallel (Marder et al., 1989, 1994).

In (I), the angle θm between the dipolar axis (approximated as the N1—N3 vector) and the crystallographic b axis is 74.33°. The optimal θm value for SHG phase matching in the m symmetry point group is 35.26° (Zyss & Oudar, 1982). Hence, although the structure is not optimized for SHG, it is anticipated that (I) will exhibit substantial bulk quadratic NLO effects, especially electro-optic behaviour.

Experimental top

A solution of N-phenylpicolinium chloride hydrate (220 mg, 0.878 mmol), N,N'-dimethyl-4-nitrosoaniline (Aldrich; 219 mg, 1.458 mmol) and piperidine (Lancaster Synthesis; 2 drops) in methanol (grade?, Merck; 15 ml) was heated under reflux for 1.5 h. The addition of diethyl ether (grade?, Merck; volume?) to the purple solution afforded a dark precipitate, which was filtered off, washed with diethyl ether and dried. The crude chloride salt was metathesized to the PF6 salt by precipitation from water/aqueous NH4PF6 (Acros) and purified by column chromatography [silica gel, 70–230 mesh (Aldrich), acetone (Merck)/dichloromethane (Merck) 1:10], followed by precipitation from acetone/diethyl ether (yield 59 mg, 14%). Analysis calculated for C20H20F6N3P: C 53.69, H 4.51, N 9.39%; found: C 53.99, H 4.57, N 9.21%. Spectroscopic analysis: 1H NMR (200 MHz, CD3CN, δ, p.p.m.): 9.31 (2H, d, J = 7.0 Hz, C5H4N), 9.07 (1H, s, CH), 8.66 (2H, d, J = 7.0 Hz, C5H4N), 8.01–7.96 (2H, m, Ph), 7.84–7.79 (3H, m, Ph), 7.61 (2H, d, J = 9.1 Hz, C6H4), 6.87 (2H, d, J = 9.2 Hz, C6H4), 3.11 (6H, s, NMe2); MS, m/z: 302, [M - PF6]+; λmax/nm (ε/M−1 dm3) 534 (32,900), 284 (16,500). Crystals of (I) suitable for single-crystal X-ray diffraction measurements were obtained by slow evaporation of an acetonitrile (Rathburn) solution at room temperature.

Refinement top

All H atoms were refined in idealized positions using a riding model (C—H 0.93 and 0.96 Å) and their isotropic displacement parameters were allowed to refine freely.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. A representation of the molecular structure of (I), with 50% probability displacement ellipsoids. H atoms are drawn as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A crystal packing diagram for (I), viewed along the b axis.
trans-4-[4-(Dimethylamino)phenyliminomethyl]-N-phenylpyridinium hexafluorophosphate top
Crystal data top
C20H20N3+·PF6F(000) = 920
Mr = 447.36Dx = 1.531 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 19.3044 (4) ÅCell parameters from 3729 reflections
b = 10.6009 (3) Åθ = 2.9–40.2°
c = 11.6549 (3) ŵ = 0.21 mm1
β = 125.527 (2)°T = 150 K
V = 1941.10 (8) Å3Block, black
Z = 40.1 × 0.1 × 0.1 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
3240 independent reflections
Radiation source: Nonius FR591 rotating anode2945 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ϕ and ω scans to fill Ewald sphereθmax = 26.0°, θmin = 3.6°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 2323
Tmin = 0.979, Tmax = 0.979k = 1213
6150 measured reflectionsl = 1312
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0611P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.22 e Å3
3240 reflectionsΔρmin = 0.21 e Å3
292 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0126 (13)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.01 (9)
Crystal data top
C20H20N3+·PF6V = 1941.10 (8) Å3
Mr = 447.36Z = 4
Monoclinic, CcMo Kα radiation
a = 19.3044 (4) ŵ = 0.21 mm1
b = 10.6009 (3) ÅT = 150 K
c = 11.6549 (3) Å0.1 × 0.1 × 0.1 mm
β = 125.527 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
3240 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
2945 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.979Rint = 0.028
6150 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.092Δρmax = 0.22 e Å3
S = 1.00Δρmin = 0.21 e Å3
3240 reflectionsAbsolute structure: Flack (1983)
292 parametersAbsolute structure parameter: 0.01 (9)
2 restraints
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
N10.24675 (13)0.37546 (19)0.4277 (2)0.0281 (4)
N20.07694 (13)0.5322 (2)0.5957 (2)0.0302 (5)
N30.11816 (14)0.6445 (2)0.7961 (3)0.0411 (6)
C10.29748 (15)0.3621 (2)0.3741 (2)0.0279 (5)
C20.37421 (17)0.4255 (2)0.4405 (3)0.0322 (6)
H20.39280.47590.51870.047 (8)*
C30.42324 (17)0.4132 (2)0.3888 (3)0.0369 (7)
H30.47530.45430.43290.043 (8)*
C40.39333 (17)0.3386 (2)0.2704 (3)0.0367 (6)
H40.42530.33100.23440.029 (7)*
C50.31675 (16)0.2757 (2)0.2059 (3)0.0351 (6)
H50.29770.22610.12690.040 (8)*
C60.26808 (16)0.2857 (2)0.2576 (3)0.0312 (5)
H60.21690.24220.21540.033 (7)*
C70.14696 (15)0.4046 (2)0.5252 (2)0.0288 (5)
C80.17283 (17)0.2858 (2)0.5134 (3)0.0316 (5)
H80.15660.21460.53890.044 (8)*
C90.22194 (16)0.2730 (2)0.4644 (3)0.0301 (5)
H90.23850.19300.45630.052 (9)*
C100.22193 (16)0.4926 (2)0.4380 (3)0.0291 (5)
H100.23910.56270.41240.034 (7)*
C110.17241 (15)0.5092 (2)0.4850 (2)0.0290 (5)
H110.15550.58990.49040.045 (8)*
C120.09424 (15)0.4203 (2)0.5760 (3)0.0304 (5)
H120.07310.35010.59410.035 (7)*
C130.02629 (15)0.5525 (2)0.6431 (3)0.0285 (5)
C140.01263 (15)0.4589 (2)0.6732 (3)0.0311 (5)
H140.00560.37460.66030.022 (6)*
C150.06039 (16)0.4889 (2)0.7210 (3)0.0317 (5)
H150.08570.42470.73890.036 (7)*
C160.07240 (16)0.6169 (2)0.7440 (3)0.0313 (5)
C170.03350 (16)0.7098 (2)0.7149 (3)0.0339 (6)
H170.03950.79420.72950.032 (7)*
C180.01388 (16)0.6783 (2)0.6646 (3)0.0327 (6)
H180.03820.74240.64440.048 (9)*
C190.16634 (18)0.5472 (3)0.8099 (3)0.0395 (7)
H19A0.19400.58360.84890.083 (13)*
H19B0.12840.48170.87110.057 (10)*
H19C0.20840.51240.71870.037 (7)*
C200.1200 (2)0.7718 (3)0.8387 (3)0.0448 (7)
H20A0.15450.77440.87350.098 (15)*
H20B0.14350.82730.75920.046 (8)*
H20C0.06310.79820.91170.096 (15)*
P10.62278 (4)0.41335 (5)0.31783 (7)0.02990 (18)
F10.67777 (11)0.30287 (16)0.3124 (2)0.0500 (4)
F20.56834 (12)0.52115 (16)0.3248 (2)0.0555 (5)
F30.70799 (11)0.46850 (15)0.45444 (18)0.0554 (5)
F40.60867 (11)0.32515 (17)0.41289 (19)0.0534 (5)
F50.63678 (12)0.5012 (2)0.2230 (2)0.0633 (5)
F60.53763 (10)0.35838 (17)0.17980 (17)0.0505 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0281 (11)0.0258 (11)0.0272 (10)0.0018 (9)0.0143 (9)0.0003 (8)
N20.0270 (11)0.0332 (12)0.0247 (10)0.0022 (9)0.0118 (9)0.0011 (8)
N30.0408 (14)0.0332 (13)0.0562 (15)0.0030 (10)0.0321 (12)0.0114 (11)
C10.0276 (13)0.0246 (12)0.0304 (13)0.0047 (10)0.0162 (11)0.0045 (9)
C20.0314 (15)0.0272 (13)0.0360 (13)0.0002 (10)0.0185 (12)0.0027 (11)
C30.0308 (15)0.0285 (14)0.0483 (17)0.0003 (10)0.0213 (14)0.0064 (11)
C40.0337 (15)0.0348 (15)0.0467 (15)0.0099 (12)0.0263 (13)0.0081 (12)
C50.0354 (15)0.0320 (14)0.0369 (14)0.0093 (11)0.0204 (12)0.0047 (11)
C60.0251 (12)0.0283 (13)0.0344 (13)0.0032 (10)0.0139 (11)0.0011 (10)
C70.0235 (13)0.0326 (14)0.0234 (12)0.0039 (10)0.0097 (11)0.0007 (9)
C80.0316 (13)0.0289 (13)0.0274 (12)0.0034 (10)0.0133 (11)0.0024 (10)
C90.0290 (13)0.0271 (13)0.0294 (12)0.0033 (10)0.0141 (11)0.0007 (10)
C100.0304 (13)0.0247 (12)0.0288 (12)0.0033 (10)0.0153 (11)0.0004 (10)
C110.0287 (13)0.0273 (13)0.0265 (12)0.0027 (10)0.0136 (11)0.0005 (10)
C120.0265 (13)0.0340 (14)0.0269 (12)0.0054 (10)0.0133 (11)0.0017 (9)
C130.0234 (12)0.0298 (12)0.0258 (12)0.0019 (10)0.0105 (10)0.0005 (10)
C140.0297 (14)0.0232 (13)0.0371 (14)0.0016 (10)0.0175 (12)0.0021 (10)
C150.0318 (13)0.0267 (13)0.0394 (14)0.0057 (11)0.0223 (12)0.0036 (10)
C160.0238 (13)0.0314 (13)0.0321 (13)0.0007 (11)0.0124 (11)0.0038 (11)
C170.0304 (14)0.0227 (12)0.0354 (13)0.0009 (10)0.0116 (11)0.0005 (10)
C180.0289 (13)0.0259 (13)0.0313 (13)0.0029 (10)0.0107 (12)0.0029 (10)
C190.0300 (15)0.0484 (17)0.0412 (16)0.0022 (13)0.0213 (14)0.0088 (13)
C200.0419 (17)0.0374 (16)0.0468 (16)0.0034 (12)0.0210 (15)0.0112 (13)
P10.0292 (3)0.0244 (3)0.0335 (3)0.0010 (3)0.0167 (3)0.0003 (3)
F10.0422 (10)0.0440 (9)0.0675 (12)0.0033 (8)0.0339 (9)0.0112 (8)
F20.0578 (11)0.0338 (9)0.0776 (13)0.0132 (8)0.0409 (10)0.0020 (8)
F30.0465 (10)0.0397 (10)0.0461 (10)0.0051 (8)0.0077 (8)0.0070 (8)
F40.0631 (12)0.0481 (9)0.0616 (11)0.0058 (9)0.0435 (10)0.0180 (8)
F50.0553 (12)0.0724 (13)0.0633 (12)0.0022 (9)0.0350 (10)0.0274 (10)
F60.0358 (10)0.0496 (10)0.0463 (10)0.0052 (8)0.0126 (8)0.0110 (8)
Geometric parameters (Å, º) top
N1—C91.353 (3)C10—H100.9300
N1—C101.361 (3)C11—H110.9300
N1—C11.443 (3)C12—H120.9300
N2—C121.288 (3)C13—C181.403 (4)
N2—C131.392 (3)C13—C141.406 (3)
N3—C161.363 (3)C14—C151.362 (3)
N3—C201.445 (4)C14—H140.9300
N3—C191.459 (3)C15—C161.428 (4)
C1—C21.383 (4)C15—H150.9300
C1—C61.388 (3)C16—C171.395 (4)
C2—C31.392 (4)C17—C181.384 (4)
C2—H20.9300C17—H170.9300
C3—C41.392 (4)C18—H180.9300
C3—H30.9300C19—H19A0.9600
C4—C51.380 (4)C19—H19B0.9600
C4—H40.9300C19—H19C0.9600
C5—C61.384 (3)C20—H20A0.9600
C5—H50.9300C20—H20B0.9600
C6—H60.9300C20—H20C0.9600
C7—C81.391 (4)P1—F51.5839 (18)
C7—C111.399 (3)P1—F21.5863 (16)
C7—C121.454 (3)P1—F41.5897 (16)
C8—C91.368 (4)P1—F31.5933 (17)
C8—H80.9300P1—F61.5988 (17)
C9—H90.9300P1—F11.6061 (16)
C10—C111.362 (3)
C9—N1—C10119.8 (2)N2—C13—C14126.2 (2)
C9—N1—C1120.8 (2)C18—C13—C14117.1 (2)
C10—N1—C1119.3 (2)C15—C14—C13121.6 (2)
C12—N2—C13121.9 (2)C15—C14—H14119.2
C16—N3—C20120.3 (2)C13—C14—H14119.2
C16—N3—C19121.1 (2)C14—C15—C16121.4 (2)
C20—N3—C19118.6 (2)C14—C15—H15119.3
C2—C1—C6121.8 (2)C16—C15—H15119.3
C2—C1—N1119.1 (2)N3—C16—C17122.4 (2)
C6—C1—N1119.1 (2)N3—C16—C15120.4 (2)
C1—C2—C3119.3 (2)C17—C16—C15117.1 (2)
C1—C2—H2120.4C18—C17—C16121.0 (2)
C3—C2—H2120.4C18—C17—H17119.5
C4—C3—C2119.2 (3)C16—C17—H17119.5
C4—C3—H3120.4C17—C18—C13121.9 (2)
C2—C3—H3120.4C17—C18—H18119.1
C5—C4—C3120.7 (2)C13—C18—H18119.1
C5—C4—H4119.6N3—C19—H19A109.5
C3—C4—H4119.6N3—C19—H19B109.5
C4—C5—C6120.6 (2)H19A—C19—H19B109.5
C4—C5—H5119.7N3—C19—H19C109.5
C6—C5—H5119.7H19A—C19—H19C109.5
C5—C6—C1118.4 (2)H19B—C19—H19C109.5
C5—C6—H6120.8N3—C20—H20A109.5
C1—C6—H6120.8N3—C20—H20B109.5
C8—C7—C11118.0 (2)H20A—C20—H20B109.5
C8—C7—C12121.4 (2)N3—C20—H20C109.5
C11—C7—C12120.7 (2)H20A—C20—H20C109.5
C9—C8—C7120.4 (2)H20B—C20—H20C109.5
C9—C8—H8119.8F5—P1—F289.94 (10)
C7—C8—H8119.8F5—P1—F4179.95 (19)
N1—C9—C8120.7 (2)F2—P1—F490.06 (10)
N1—C9—H9119.6F5—P1—F389.19 (11)
C8—C9—H9119.6F2—P1—F390.83 (11)
N1—C10—C11121.2 (2)F4—P1—F390.85 (10)
N1—C10—H10119.4F5—P1—F690.27 (11)
C11—C10—H10119.4F2—P1—F689.41 (11)
C10—C11—C7119.8 (2)F4—P1—F689.68 (10)
C10—C11—H11120.1F3—P1—F6179.41 (11)
C7—C11—H11120.1F5—P1—F190.97 (11)
N2—C12—C7119.5 (2)F2—P1—F1179.09 (11)
N2—C12—H12120.2F4—P1—F189.03 (9)
C7—C12—H12120.2F3—P1—F189.12 (10)
N2—C13—C18116.7 (2)F6—P1—F190.65 (10)

Experimental details

Crystal data
Chemical formulaC20H20N3+·PF6
Mr447.36
Crystal system, space groupMonoclinic, Cc
Temperature (K)150
a, b, c (Å)19.3044 (4), 10.6009 (3), 11.6549 (3)
β (°) 125.527 (2)
V3)1941.10 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.1 × 0.1 × 0.1
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.979, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
6150, 3240, 2945
Rint0.028
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.092, 1.00
No. of reflections3240
No. of parameters292
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.21
Absolute structureFlack (1983)
Absolute structure parameter0.01 (9)

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), DENZO and COLLECT, DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
N1—C91.353 (3)C5—C61.384 (3)
N1—C101.361 (3)C7—C81.391 (4)
N1—C11.443 (3)C7—C111.399 (3)
N2—C121.288 (3)C7—C121.454 (3)
N2—C131.392 (3)C8—C91.368 (4)
N3—C161.363 (3)C10—C111.362 (3)
N3—C201.445 (4)C13—C181.403 (4)
N3—C191.459 (3)C13—C141.406 (3)
C1—C21.383 (4)C14—C151.362 (3)
C1—C61.388 (3)C15—C161.428 (4)
C2—C31.392 (4)C16—C171.395 (4)
C3—C41.392 (4)C17—C181.384 (4)
C4—C51.380 (4)
C9—N1—C10119.8 (2)C11—C7—C12120.7 (2)
C9—N1—C1120.8 (2)C9—C8—C7120.4 (2)
C10—N1—C1119.3 (2)N1—C9—C8120.7 (2)
C12—N2—C13121.9 (2)N1—C10—C11121.2 (2)
C16—N3—C20120.3 (2)C10—C11—C7119.8 (2)
C16—N3—C19121.1 (2)N2—C12—C7119.5 (2)
C20—N3—C19118.6 (2)N2—C13—C18116.7 (2)
C2—C1—C6121.8 (2)N2—C13—C14126.2 (2)
C2—C1—N1119.1 (2)C18—C13—C14117.1 (2)
C6—C1—N1119.1 (2)C15—C14—C13121.6 (2)
C1—C2—C3119.3 (2)C14—C15—C16121.4 (2)
C4—C3—C2119.2 (3)N3—C16—C17122.4 (2)
C5—C4—C3120.7 (2)N3—C16—C15120.4 (2)
C4—C5—C6120.6 (2)C17—C16—C15117.1 (2)
C5—C6—C1118.4 (2)C18—C17—C16121.0 (2)
C8—C7—C11118.0 (2)C17—C18—C13121.9 (2)
C8—C7—C12121.4 (2)
 

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