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Two polymorphs, α and γ, of the title compound, C22H20N2O2, have been characterized by means of single-crystal synchrotron X-ray diffraction. In the α form, the mol­ecules pack in a herring-bone fashion, linked via weak C—H...N intermolecular interactions (H...N 2.58 Å). In the γ form, the mol­ecules are arranged in nearly planar sheets, which form a network held together by intermolecular hydrogen bonds of the type C—H...O (H...O 2.49 Å) and C—H...N (H...N 2.50 Å). The stacking distance between the sheets is 3.40 Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010337/bm1420sup1.cif
Contains datablocks global, a-form, g-form

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010337/bm1420a-formsup2.hkl
Contains datablock a-form

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010337/bm1420g-formsup3.hkl
Contains datablock g-form

CCDC references: 152636; 152637

Comment top

The discovery that semiconducting polymers based on polyphenylenevinylene (PPV) have interesting and useful electroluminescent properties has led to their successful development as components in light-emitting diodes (LEDs) and other semiconducting devices (Burroughes et al., 1990; Braun & Heeger, 1991). The characteristics and efficiencies of these devices have been improved by the introduction of electron-withdrawing substituents on the PPV backbone which lower the barrier to electron injection (Bredas & Heeger, 1994). Another way to achieve high electron affinity is to incorporate electronegative hetero atoms into the polymer backbone. Evidence for this has been found in work on oligomers based on distyrylpyrazine which show promise as emissive and/or charge-transport agents for LED devices. In particular, devices made with the dimethoxy derivative 2,5-bis[2-(4-methoxyphenyl)ethenyl]pyrazine, (I), have been shown to have a higher electron affinity than PPV itself (Nohara et al., 1990; Grimsdale et al., 1997). To understand this effect properly, it is necessary first to obtain a detailed knowledge of the structure of the oligomer in the solid state. The parent compound, 2,5-distyrylpyrazine, has two known polymorphic forms, an orthorhombic α-form (Sasada et al., 1971) and a monoclinic γ-form (Nakanishi et al., 1976); the very similar polymorphic forms found for the title dimethoxy derivative, (I), have accordingly been denoted α and γ. \sch

Preliminary measurements were made on laboratory X-ray diffractometers, but due to the weak diffraction of both forms it was necessary to exploit the high intensity of a synchrotron radiation source to determine the crystal structures accurately. These determinations represent the first reported crystal structures of a substituted 2,5-distyrylpyrazine.

Both forms of (I) have one half molecule in the asymmetric unit and the two rings attached to each double bond are mutually trans. The bond lengths and angles are comparable, but there is a difference in the molecular planarity of the two forms caused by differences in the reciprocal orientation of the aromatic rings. Molecules in the γ-form are slightly more planar, with r.m.s. torsional deviations from planarity of 3.5 (2) and 3.3 (2)° for the lateral and central rings, respectively, compared with 3.6 (2) and 4.2 (2)° in the α-form.

The crystal packing of the two forms is quite different, with a herringbone type of arrangement in the α-form (Fig. 2), and a π-π type of stacking in the γ-form. In the latter, the molecules form a nearly planar network held together by two types of intermolecular hydrogen bonds: C—H···O through the methoxy groups, with H···O 2.49 Å, and C—H···N through the pyrazine rings, with H···N 2.50 Å (Fig. 3). The stacking distance between these pseudoplanes is 3.40 Å, calculated between a pyrazine centroid in one plane and a nearest neighbour CC bond in the next. In the α-form there are also intermolecular interactions of the type C—H···N (H···N 2.58 Å), in this case linking pyrazine rings to phenyl H atoms. Also in the crystal of (I), the phenyl and pyrazine rings of neighbouring molecules are found aligned face to face, suggesting the possible presence of quadrupole-quadrupole interactions.

The most striking result of this work is the evidence found for intermolecular hydrogen bonding through the pyrazine and methoxy groups, and the different roles it plays in the crystal packing and degree of torsion of the conjugated backbone in the two polymorphs.

Experimental top

The synthesis of compound (I) is described elsewhere by Grimsdale et al. (1997). The γ-form was obtained as thick yellow plates? green blocks in tables? by slow evaporation of solvent at 278 K from a solution of (I) in CH2Cl2. Fast evaporation of solvent from the same solution at 298 K yielded very thin green plates? needle in tables? of the α-form.

Refinement top

H atoms were placed geometrically, with Csp2—H 0.95 Å and Csp3—H 0.98 Å, and refined riding on their respective carrier atoms with Uiso(H) = 1.2Ueq(C). The program PLATON (Spek, 1990) was used to calculate the hydrogen bonding interactions using C—H distances normalized to the neutron-derived value of 1.08 Å.

Computing details top

For both compounds, data collection: SMART (Bruker, 1998); cell refinement: LSCELL (Clegg, 1995); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SCHAKAL97 (Keller, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The molecular structures of a) the α form and b) the γ form of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the ??% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The herringbone type of packing in the α-form of (I), showing the C—H···N intermolecular interactions (H···N 2.58 Å).
[Figure 3] Fig. 3. The nearly planar network in the γ-form of (I), showing the C—H···O and C—H···N interactions (H···O 2.49 Å and H···N 2.50 Å). The π-π stacking distance between these pseudoplanes is 3.40 Å.
(a-form) top
Crystal data top
C22H20N2O2F(000) = 728
Mr = 344.40Dx = 1.313 Mg m3
Orthorhombic, PccnSynchrotron radiation, λ = 0.68910 Å
Hall symbol: -P 2ab 2acCell parameters from 5802 reflections
a = 9.124 (1) Åθ = 3.1–29.3°
b = 26.061 (3) ŵ = 0.09 mm1
c = 7.328 (1) ÅT = 150 K
V = 1742.5 (4) Å3Needle, green
Z = 40.18 × 0.04 × 0.01 mm
Data collection top
Bruker SMART CCD
diffractometer
2502 independent reflections
Radiation source: Daresbury SRS, Station 9.8 (Greaves et al., 1997; Clegg et al., 1998)1979 reflections with I > 2σ(I)
Silicon 111 monochromatorRint = 0.035
Detector resolution: 8.192 pixels mm-1θmax = 29.4°, θmin = 2.3°
thin slice, ω–scansh = 127
Absorption correction: multi-scan
SADABS (Sheldrick, 1997)
k = 3636
Tmin = 0.985, Tmax = 0.998l = 1010
9157 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.8532P]
where P = (Fo2 + 2Fc2)/3
2502 reflections(Δ/σ)max = 0.007
119 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C22H20N2O2V = 1742.5 (4) Å3
Mr = 344.40Z = 4
Orthorhombic, PccnSynchrotron radiation, λ = 0.68910 Å
a = 9.124 (1) ŵ = 0.09 mm1
b = 26.061 (3) ÅT = 150 K
c = 7.328 (1) Å0.18 × 0.04 × 0.01 mm
Data collection top
Bruker SMART CCD
diffractometer
2502 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick, 1997)
1979 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.998Rint = 0.035
9157 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.12Δρmax = 0.34 e Å3
2502 reflectionsΔρmin = 0.28 e Å3
119 parameters
Special details top

Experimental. Diffraction intensities for the two polymorphs (α-form and γ-form) were collected at the Daresbury SRS (UK), Station 9.8 (Greaves et al., 1997; Clegg et al., 1998), using a Bruker AXS SMART CCD area-detector diffractometer. Intensities were integrated from several series of exposures. For the α-form, each exposure covered 0.45° in ω, with an exposure time of 1 s; for the γ-form, each exposure covered 0.3° in ω, with an exposure time of 3 s. In both cases, the total data sets were more than a hemisphere. Data were corrected for absorption and incident beam decay (Sheldrick, 1997). The program PLATON (Spek, 1990) was used to calculate the hydrogen-bonding interactions using normalized C—H distances to the neutron derived value (1.08 Å). For all molecular representations, the graphics program SCHAKAL97 (Keller, 1997) was used.

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
O10.03673 (13)0.70252 (5)0.54373 (16)0.0320 (3)
N10.10940 (12)0.49301 (5)0.63293 (17)0.0214 (3)
C10.01382 (16)0.66890 (6)0.4036 (2)0.0229 (3)
C20.09905 (16)0.63315 (6)0.3974 (2)0.0226 (3)
H20.16760.63080.49470.027*
C30.11050 (15)0.60076 (6)0.24668 (19)0.0209 (3)
H30.18740.57620.24310.025*
C40.01271 (15)0.60328 (5)0.10124 (19)0.0188 (3)
C50.09976 (15)0.64000 (6)0.1111 (2)0.0234 (3)
H50.16790.64270.01360.028*
C60.11312 (16)0.67216 (6)0.2594 (2)0.0252 (3)
H60.19020.69660.26340.030*
C70.03328 (15)0.56864 (5)0.05300 (19)0.0200 (3)
H70.11450.54590.04640.024*
C80.05018 (15)0.56547 (6)0.2031 (2)0.0206 (3)
H80.13370.58710.21080.025*
C90.02112 (14)0.53096 (5)0.35512 (19)0.0189 (3)
C100.12769 (15)0.52338 (6)0.4896 (2)0.0215 (3)
H100.21830.54100.47760.026*
C110.0667 (2)0.70142 (7)0.6900 (2)0.0365 (4)
H11A0.16470.70920.64280.055*
H11B0.03940.72700.78180.055*
H11C0.06690.66720.74590.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0385 (6)0.0306 (6)0.0268 (6)0.0055 (5)0.0029 (5)0.0091 (5)
N10.0179 (5)0.0250 (6)0.0212 (6)0.0014 (4)0.0015 (4)0.0011 (5)
C10.0262 (7)0.0209 (7)0.0216 (7)0.0023 (5)0.0024 (6)0.0008 (5)
C20.0234 (7)0.0250 (7)0.0194 (6)0.0007 (5)0.0011 (5)0.0018 (5)
C30.0190 (6)0.0238 (7)0.0200 (7)0.0009 (5)0.0006 (5)0.0011 (5)
C40.0169 (6)0.0210 (7)0.0186 (6)0.0022 (5)0.0016 (5)0.0010 (5)
C50.0201 (7)0.0276 (7)0.0226 (7)0.0010 (5)0.0033 (5)0.0011 (6)
C60.0226 (7)0.0249 (7)0.0280 (7)0.0044 (6)0.0000 (6)0.0010 (6)
C70.0182 (6)0.0218 (7)0.0199 (6)0.0012 (5)0.0019 (5)0.0005 (5)
C80.0174 (6)0.0231 (7)0.0214 (7)0.0011 (5)0.0010 (5)0.0005 (5)
C90.0167 (6)0.0217 (6)0.0184 (6)0.0031 (5)0.0013 (5)0.0010 (5)
C100.0163 (6)0.0255 (7)0.0226 (7)0.0003 (5)0.0011 (5)0.0013 (5)
C110.0509 (10)0.0314 (8)0.0271 (8)0.0006 (8)0.0069 (8)0.0084 (7)
Geometric parameters (Å, º) top
O1—C11.3658 (18)C5—H50.9500
O1—C111.428 (2)C6—H60.9500
N1—C101.3257 (19)C7—C81.3406 (19)
N1—C9i1.3477 (17)C7—H70.9500
C1—C21.389 (2)C8—C91.4558 (19)
C1—C61.395 (2)C8—H80.9500
C2—C31.394 (2)C9—N1i1.3477 (17)
C2—H20.9500C9—C101.3985 (19)
C3—C41.3914 (19)C10—H100.9500
C3—H30.9500C11—H11A0.9800
C4—C51.4051 (19)C11—H11B0.9800
C4—C71.4585 (19)C11—H11C0.9800
C5—C61.377 (2)
C1—O1—C11116.75 (13)C1—C6—H6119.9
C10—N1—C9i116.08 (12)C8—C7—C4126.95 (13)
O1—C1—C2124.63 (14)C8—C7—H7116.5
O1—C1—C6115.55 (13)C4—C7—H7116.5
C2—C1—C6119.82 (14)C7—C8—C9124.23 (13)
C1—C2—C3119.18 (13)C7—C8—H8117.9
C1—C2—H2120.4C9—C8—H8117.9
C3—C2—H2120.4N1i—C9—C10120.21 (13)
C4—C3—C2122.03 (13)N1i—C9—C8119.80 (12)
C4—C3—H3119.0C10—C9—C8119.98 (12)
C2—C3—H3119.0N1—C10—C9123.72 (13)
C3—C4—C5117.44 (13)N1—C10—H10118.1
C3—C4—C7118.81 (12)C9—C10—H10118.1
C5—C4—C7123.74 (13)O1—C11—H11A109.5
C6—C5—C4121.31 (14)O1—C11—H11B109.5
C6—C5—H5119.3H11A—C11—H11B109.5
C4—C5—H5119.3O1—C11—H11C109.5
C5—C6—C1120.22 (14)H11A—C11—H11C109.5
C5—C6—H6119.9H11B—C11—H11C109.5
C11—O1—C1—C22.2 (2)O1—C1—C6—C5179.95 (14)
C11—O1—C1—C6177.63 (14)C2—C1—C6—C50.1 (2)
O1—C1—C2—C3179.78 (14)C3—C4—C7—C8179.51 (14)
C6—C1—C2—C30.4 (2)C5—C4—C7—C81.5 (2)
C1—C2—C3—C40.4 (2)C4—C7—C8—C9178.12 (13)
C2—C3—C4—C50.0 (2)C7—C8—C9—N1i12.8 (2)
C2—C3—C4—C7179.02 (13)C7—C8—C9—C10168.16 (14)
C3—C4—C5—C60.2 (2)C9i—N1—C10—C90.3 (2)
C7—C4—C5—C6179.27 (14)N1i—C9—C10—N10.4 (2)
C4—C5—C6—C10.2 (2)C8—C9—C10—N1179.39 (14)
Symmetry code: (i) x, y+1, z+1.
(g-form) top
Crystal data top
C22H20N2O2F(000) = 728
Mr = 344.40Dx = 1.345 Mg m3
Monoclinic, C2/cSynchrotron radiation, λ = 0.68910 Å
a = 32.339 (6) ÅCell parameters from 4261 reflections
b = 5.732 (1) Åθ = 3.6–29.3°
c = 9.411 (2) ŵ = 0.09 mm1
β = 102.815 (4)°T = 150 K
V = 1701.0 (6) Å3Block, yellow
Z = 40.14 × 0.12 × 0.10 mm
Data collection top
Bruker SMART CCD
diffractometer
2384 independent reflections
Radiation source: Daresbury SRS, Station 9.8 (Greaves et al., 1997; Clegg et al., 1998)1937 reflections with I > 2σ(I)
Silicon 111 monochromatorRint = 0.032
Detector resolution: 8.192 pixels mm-1θmax = 29.4°, θmin = 2.5°
thin slice, ω–scansh = 4345
Absorption correction: multi-scan
SADABS (Sheldrick, 1997)
k = 85
Tmin = 0.988, Tmax = 0.991l = 1311
5705 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0801P)2 + 0.6111P]
where P = (Fo2 + 2Fc2)/3
2384 reflections(Δ/σ)max = 0.009
119 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C22H20N2O2V = 1701.0 (6) Å3
Mr = 344.40Z = 4
Monoclinic, C2/cSynchrotron radiation, λ = 0.68910 Å
a = 32.339 (6) ŵ = 0.09 mm1
b = 5.732 (1) ÅT = 150 K
c = 9.411 (2) Å0.14 × 0.12 × 0.10 mm
β = 102.815 (4)°
Data collection top
Bruker SMART CCD
diffractometer
2384 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick, 1997)
1937 reflections with I > 2σ(I)
Tmin = 0.988, Tmax = 0.991Rint = 0.032
5705 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.141H-atom parameters constrained
S = 1.09Δρmax = 0.38 e Å3
2384 reflectionsΔρmin = 0.20 e Å3
119 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.28826 (3)0.21068 (16)0.67400 (9)0.0250 (2)
N10.51819 (3)0.71235 (17)1.55555 (11)0.0191 (2)
C10.32231 (4)0.2230 (2)0.78949 (12)0.0181 (2)
C20.35269 (4)0.0489 (2)0.82793 (13)0.0195 (3)
H20.35120.08870.77080.023*
C30.38526 (4)0.07860 (19)0.95113 (12)0.0187 (2)
H30.40590.04110.97750.022*
C40.38849 (4)0.27970 (19)1.03710 (12)0.0168 (2)
C50.35776 (4)0.45371 (19)0.99423 (13)0.0193 (2)
H50.35930.59281.05010.023*
C60.32530 (4)0.4267 (2)0.87245 (13)0.0207 (3)
H60.30490.54720.84500.025*
C70.42260 (4)0.2981 (2)1.16777 (12)0.0184 (2)
H70.43800.15941.19920.022*
C80.43442 (4)0.48976 (19)1.24785 (12)0.0190 (2)
H80.42000.63181.21770.023*
C90.46837 (4)0.49131 (18)1.37919 (12)0.0169 (2)
C100.48702 (4)0.70142 (19)1.43708 (13)0.0192 (2)
H100.47690.84291.38920.023*
C110.28306 (4)0.0003 (2)0.59144 (14)0.0272 (3)
H11A0.30840.02840.55300.041*
H11B0.25820.01340.51040.041*
H11C0.27900.13070.65420.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0246 (5)0.0235 (5)0.0227 (4)0.0019 (3)0.0037 (3)0.0031 (3)
N10.0217 (5)0.0134 (4)0.0209 (5)0.0015 (3)0.0022 (4)0.0010 (3)
C10.0185 (5)0.0190 (5)0.0163 (5)0.0012 (4)0.0025 (4)0.0006 (4)
C20.0199 (5)0.0183 (5)0.0199 (5)0.0002 (4)0.0036 (4)0.0032 (4)
C30.0192 (5)0.0153 (5)0.0208 (5)0.0009 (4)0.0029 (4)0.0010 (4)
C40.0179 (5)0.0155 (5)0.0171 (5)0.0015 (4)0.0039 (4)0.0007 (4)
C50.0219 (6)0.0140 (5)0.0214 (5)0.0005 (4)0.0035 (4)0.0023 (4)
C60.0213 (6)0.0158 (5)0.0237 (6)0.0017 (4)0.0020 (4)0.0007 (4)
C70.0192 (5)0.0169 (5)0.0184 (5)0.0004 (4)0.0026 (4)0.0002 (4)
C80.0194 (5)0.0159 (5)0.0204 (5)0.0004 (4)0.0017 (4)0.0003 (4)
C90.0187 (5)0.0136 (5)0.0184 (5)0.0004 (4)0.0039 (4)0.0016 (4)
C100.0224 (6)0.0127 (5)0.0211 (5)0.0005 (4)0.0021 (4)0.0003 (4)
C110.0265 (6)0.0290 (7)0.0234 (6)0.0002 (5)0.0007 (5)0.0078 (5)
Geometric parameters (Å, º) top
O1—C11.3666 (13)C5—H50.9500
O1—C111.4269 (15)C6—H60.9500
N1—C101.3283 (14)C7—C81.3392 (16)
N1—C9i1.3455 (14)C7—H70.9500
C1—C21.3907 (16)C8—C91.4599 (15)
C1—C61.3960 (16)C8—H80.9500
C2—C31.3933 (16)C9—N1i1.3455 (14)
C2—H20.9500C9—C101.4018 (15)
C3—C41.3988 (15)C10—H100.9500
C3—H30.9500C11—H11A0.9800
C4—C51.4027 (16)C11—H11B0.9800
C4—C71.4622 (15)C11—H11C0.9800
C5—C61.3804 (16)
C1—O1—C11116.98 (9)C1—C6—H6119.9
C10—N1—C9i116.76 (10)C8—C7—C4126.90 (11)
O1—C1—C2124.60 (10)C8—C7—H7116.5
O1—C1—C6115.58 (10)C4—C7—H7116.5
C2—C1—C6119.82 (10)C7—C8—C9123.28 (10)
C1—C2—C3119.28 (10)C7—C8—H8118.4
C1—C2—H2120.4C9—C8—H8118.4
C3—C2—H2120.4N1i—C9—C10120.03 (10)
C2—C3—C4121.84 (10)N1i—C9—C8119.16 (10)
C2—C3—H3119.1C10—C9—C8120.81 (10)
C4—C3—H3119.1N1—C10—C9123.21 (10)
C3—C4—C5117.54 (10)N1—C10—H10118.4
C3—C4—C7119.44 (10)C9—C10—H10118.4
C5—C4—C7123.00 (10)O1—C11—H11A109.5
C6—C5—C4121.25 (10)O1—C11—H11B109.5
C6—C5—H5119.4H11A—C11—H11B109.5
C4—C5—H5119.4O1—C11—H11C109.5
C5—C6—C1120.25 (10)H11A—C11—H11C109.5
C5—C6—H6119.9H11B—C11—H11C109.5
C11—O1—C1—C22.49 (17)O1—C1—C6—C5177.97 (11)
C11—O1—C1—C6176.86 (11)C2—C1—C6—C51.41 (18)
O1—C1—C2—C3177.92 (11)C3—C4—C7—C8168.23 (12)
C6—C1—C2—C31.41 (18)C5—C4—C7—C813.20 (19)
C1—C2—C3—C40.41 (18)C4—C7—C8—C9178.58 (11)
C2—C3—C4—C50.57 (17)C7—C8—C9—N1i16.69 (18)
C2—C3—C4—C7178.08 (11)C7—C8—C9—C10163.10 (12)
C3—C4—C5—C60.57 (17)C9i—N1—C10—C90.28 (19)
C7—C4—C5—C6178.03 (11)N1i—C9—C10—N10.3 (2)
C4—C5—C6—C10.41 (18)C8—C9—C10—N1179.49 (11)
Symmetry code: (i) x+1, y+1, z+3.

Experimental details

(a-form)(g-form)
Crystal data
Chemical formulaC22H20N2O2C22H20N2O2
Mr344.40344.40
Crystal system, space groupOrthorhombic, PccnMonoclinic, C2/c
Temperature (K)150150
a, b, c (Å)9.124 (1), 26.061 (3), 7.328 (1)32.339 (6), 5.732 (1), 9.411 (2)
α, β, γ (°)90, 90, 9090, 102.815 (4), 90
V3)1742.5 (4)1701.0 (6)
Z44
Radiation typeSynchrotron, λ = 0.68910 ÅSynchrotron, λ = 0.68910 Å
µ (mm1)0.090.09
Crystal size (mm)0.18 × 0.04 × 0.010.14 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART CCD
diffractometer
Bruker SMART CCD
diffractometer
Absorption correctionMulti-scan
SADABS (Sheldrick, 1997)
Multi-scan
SADABS (Sheldrick, 1997)
Tmin, Tmax0.985, 0.9980.988, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
9157, 2502, 1979 5705, 2384, 1937
Rint0.0350.032
(sin θ/λ)max1)0.7130.713
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.138, 1.12 0.049, 0.141, 1.09
No. of reflections25022384
No. of parameters119119
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.280.38, 0.20

Computer programs: SMART (Bruker, 1998), LSCELL (Clegg, 1995), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SCHAKAL97 (Keller, 1997), SHELXL97 and PLATON (Spek, 1990).

 

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