Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012340/cf6258sup1.cif | |
Rietveld powder data file (CIF format) https://doi.org/10.1107/S1600536803012340/cf6258Isup2.rtv |
CCDC reference: 217599
Key indicators
- Powder X-ray study
- T = 293 K
- Mean (C-C) = 0.090 Å
- R factor = 0.000
- wR factor = 0.000
- Data-to-parameter ratio = 0.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
REFLT_03 _reflns_number_total not in the CIF REFNR_01 Alert A Ratio of reflections to parameters is < 6 for a centrosymmetric structure sine(theta)/lambda 0.3246 Proportion of unique data used NaN Ratio reflections to parameters 0.0000 THETM_01 Alert A The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.3246
Alert Level C:
RADNW_01 Alert C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54056 PLAT_721 Alert C Bond Calc 0.91967, Rep 0.93000, Dev. 0.01 Ang. C14 -H14 1.555 1.555 PLAT_722 Alert C Angle Calc 117.59, Rep 119.00, Dev. 1.41 Deg. C4 -C7 -H7 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 119.56, Rep 118.00, Dev. 1.56 Deg. C8 -C7 -H7 1.555 1.555 1.555 PLAT_722 Alert C Angle Calc 119.11, Rep 118.00, Dev. 1.11 Deg. C9 -C8 -H8 1.555 1.555 1.555 General Notes
RADNT_01 Extra text has been found in the _diffrn_radiation_type field. Radiation given as CuK\a~1~ Radiation identified as Cu K\a RADNW_01 The radiation wavelength given implies that Cu Kalpha1 has been used. Please check that this is correct. Wavelength given = 1.54056
2 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
5 Alert Level C = Please check
Compound (I) was synthesized acording to the method of Titski & Turovskaya (1990). IR spectra were measured from KBr discs, using a Specord M-80 spectrometer. NMR spectra were measured with a Bruker 300 spectrometer (300 MHz), in CDCl3 solution. Electronic spectra were measured using a Specord UV–vis spectrometer, in 96% ethanol and in chloroform.
Two X-ray powder diffraction patterns were measured in transmission mode on a Ginuier–de Wolf diffractometer and in reflection mode on an X'Pert X-ray powder diffraction system equipped with a standard resolution goniometer PW 3050/60 and proportional point detector PW 3011/20. The powder was sprinkled on the sample holder using a fine sieve to avoid preferred orientation. The thickness of the sample was no more 0.1 mm. During the exposures the specimen was spun in its plane to improve particle statistics. The unit-cell dimensions were determined with the indexing program TREOR (Werner et al., 1985) with M20 = 14 and F30 = 31, using the first 30 peak positions. The structure was solved by the grid-search procedure (Chernyshev & Schenk, 1998) and refined with the use of bond restraints by the MRIA program (Zlokazov & Chernyshev, 1992). The strength of restraints was a function of interatomic separation and, for intramolecular bond lengths, corresponds to an r.m.s. deviation of 0.03 Å. An additional restraint was applied to the planarity of the C15N2O fragment. H atoms were placed in geometrically calculated positions and allowed to refine using riding model constraints, with a common isotropic displacement parameter Uiso fixed at 0.05 Å2. A single overall Uiso parameter for non-H atoms was refined. The diffraction profiles and the differences between the measured and calculated profiles are shown in Fig. 3.
Data collection: local program; data reduction: local program; program(s) used to solve structure: MRIA (Zlokazov & Chernyshev, 1992); program(s) used to refine structure: MRIA; software used to prepare material for publication: MRIA and PARST (Nardelli, 1983).
C15H16N2O | Z = 4 |
Mr = 240.2 | F(000) = 512 |
Monoclinic, P21/n | Dx = 1.266 Mg m−3 |
a = 26.822 (4) Å | Cu Kα1 radiation, λ = 1.54056 Å |
b = 7.758 (2) Å | T = 293 K |
c = 6.079 (3) Å | Particle morphology: no specific habit |
β = 94.03 (1)° | yellow |
V = 1262 (1) Å3 | flat_sheet, 20 × 20 mm |
Philips Analytical XPert PRO X-ray diffraction system diffractometer | Data collection mode: reflection |
Radiation source: PW3373/00, line-focus sealed tube | Scan method: step |
PW3110/65, four Ge(220) crystals monochromator | 2θmin = 6°, 2θmax = 60°, 2θstep = 0.01° |
Specimen mounting: The powder was sprinkled on the sample holder through a fine sieve. The thickness of the layer was no more than 0.1 mm. |
Refinement on Inet | 162 parameters |
Least-squares matrix: full with fixed elements per cycle | 112 restraints |
Rp = 0.19 | 1 constraint |
Rwp = 0.29 | H-atom parameters constrained |
Rexp = 0.19 | Weighting scheme based on measured s.u.'s w(i) = 1/Iobs(i) at each point i |
χ2 = 2.250 | (Δ/σ)max = 0.01 |
5401 data points | Background function: Chebyshev polynomial up to the 5th order |
Profile function: split-type pseudo-Voigt (Toraya, 1986) | Preferred orientation correction: Spherical harmonics expansion (Ahtee et al., 1989) up to the 6th order. |
C15H16N2O | β = 94.03 (1)° |
Mr = 240.2 | V = 1262 (1) Å3 |
Monoclinic, P21/n | Z = 4 |
a = 26.822 (4) Å | Cu Kα1 radiation, λ = 1.54056 Å |
b = 7.758 (2) Å | T = 293 K |
c = 6.079 (3) Å | flat_sheet, 20 × 20 mm |
Philips Analytical XPert PRO X-ray diffraction system diffractometer | Scan method: step |
Specimen mounting: The powder was sprinkled on the sample holder through a fine sieve. The thickness of the layer was no more than 0.1 mm. | 2θmin = 6°, 2θmax = 60°, 2θstep = 0.01° |
Data collection mode: reflection |
Rp = 0.19 | 5401 data points |
Rwp = 0.29 | 162 parameters |
Rexp = 0.19 | 112 restraints |
χ2 = 2.250 | H-atom parameters constrained |
Experimental. specimen was rotated in its plane |
Geometry. All e.s.d.'s 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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.0708 (16) | 0.180 (6) | −0.545 (9) | 0.075 (3)* | |
C2 | 0.115 (2) | 0.269 (7) | −0.574 (12) | 0.075 (3)* | |
C3 | 0.156 (2) | 0.254 (8) | −0.425 (12) | 0.075 (3)* | |
C4 | 0.155 (2) | 0.147 (8) | −0.240 (12) | 0.075 (3)* | |
C5 | 0.111 (2) | 0.056 (8) | −0.208 (12) | 0.075 (3)* | |
C6 | 0.0696 (18) | 0.074 (8) | −0.361 (14) | 0.075 (3)* | |
C7 | 0.198 (2) | 0.130 (8) | −0.084 (11) | 0.075 (3)* | |
C8 | 0.241 (3) | 0.214 (8) | −0.106 (11) | 0.075 (3)* | |
C9 | 0.284 (2) | 0.197 (8) | 0.050 (13) | 0.075 (3)* | |
C10 | 0.328 (2) | 0.288 (7) | 0.017 (11) | 0.075 (3)* | |
C11 | 0.3689 (19) | 0.273 (8) | 0.166 (12) | 0.075 (3)* | |
C12 | 0.367 (2) | 0.165 (8) | 0.353 (11) | 0.075 (3)* | |
C13 | 0.323 (2) | 0.074 (8) | 0.385 (11) | 0.075 (3)* | |
C14 | 0.2818 (19) | 0.090 (8) | 0.235 (11) | 0.075 (3)* | |
N15 | 0.4075 (16) | 0.148 (6) | 0.502 (9) | 0.075 (3)* | |
C16 | 0.404 (2) | 0.038 (9) | 0.689 (13) | 0.075 (3)* | |
C17 | 0.452 (2) | 0.242 (7) | 0.467 (13) | 0.075 (3)* | |
O18 | 0.0320 (14) | 0.194 (5) | −0.685 (7) | 0.075 (3)* | |
H2 | 0.117 | 0.340 | −0.696 | 0.051* | |
H3 | 0.185 | 0.315 | −0.449 | 0.051* | |
H5 | 0.109 | −0.016 | −0.087 | 0.051* | |
H6 | 0.041 | 0.012 | −0.338 | 0.051* | |
H7 | 0.195 | 0.058 | 0.037 | 0.051* | |
H8 | 0.243 | 0.286 | −0.227 | 0.051* | |
H10 | 0.329 | 0.360 | −0.106 | 0.051* | |
H11 | 0.398 | 0.334 | 0.143 | 0.051* | |
H13 | 0.321 | 0.003 | 0.508 | 0.051* | |
H14 | 0.253 | 0.030 | 0.257 | 0.051* | |
H16A | 0.435 | 0.040 | 0.778 | 0.051* | |
H16B | 0.397 | −0.078 | 0.640 | 0.051* | |
H16C | 0.378 | 0.077 | 0.776 | 0.051* | |
H17A | 0.477 | 0.217 | 0.585 | 0.051* | |
H17B | 0.445 | 0.363 | 0.465 | 0.051* | |
H17C | 0.464 | 0.208 | 0.329 | 0.051* |
N15—C17 | 1.43 (8) | N1—O18 | 1.30 (6) |
N15—C16 | 1.43 (9) | C6—H6 | 0.93 |
N15—C12 | 1.37 (7) | C5—H5 | 0.93 |
C12—C11 | 1.42 (9) | C2—H2 | 0.93 |
C12—C13 | 1.41 (8) | C3—H3 | 0.93 |
C11—C10 | 1.38 (8) | C7—H7 | 0.93 |
C13—C14 | 1.38 (8) | C8—H8 | 0.93 |
C14—C9 | 1.40 (9) | C14—H14 | 0.93 |
C10—C9 | 1.40 (8) | C13—H13 | 0.93 |
C9—C8 | 1.44 (9) | C11—H11 | 0.93 |
C8—C7 | 1.34 (9) | C10—H10 | 0.93 |
C7—C4 | 1.44 (8) | C16—H16A | 0.96 |
C4—C3 | 1.40 (9) | C16—H16B | 0.96 |
C3—C2 | 1.39 (8) | C16—H16C | 0.96 |
C4—C5 | 1.40 (8) | C17—H17A | 0.96 |
C5—C6 | 1.39 (9) | C17—H17B | 0.96 |
C2—N1 | 1.39 (7) | C17—H17C | 0.96 |
C6—N1 | 1.39 (9) | ||
C6—N1—O18 | 121 (5) | C10—C9—C14 | 120 (6) |
C2—N1—O18 | 121 (4) | C9—C10—H10 | 120 |
C2—N1—C6 | 118 (5) | C9—C10—C11 | 120 (5) |
N1—C2—H2 | 119 | C11—C10—H10 | 120 |
N1—C2—C3 | 122 (5) | C10—C11—H11 | 120 |
C3—C2—H2 | 119 | C10—C11—C12 | 121 (6) |
C2—C3—H3 | 120 | C12—C11—H11 | 120 |
C2—C3—C4 | 120 (6) | C11—C12—N15 | 121 (6) |
C4—C3—H3 | 120 | C11—C12—C13 | 119 (5) |
C3—C4—C7 | 121 (6) | C13—C12—N15 | 120 (5) |
C3—C4—C5 | 119 (6) | C12—C13—H13 | 120 |
C5—C4—C7 | 120 (5) | C12—C13—C14 | 120 (5) |
C4—C5—H5 | 120 | C14—C13—H13 | 120 |
C4—C5—C6 | 120 (5) | C9—C14—C13 | 121 (6) |
C6—C5—H5 | 120 | C13—C14—H14 | 120 |
N1—C6—C5 | 122 (6) | C9—C14—H14 | 120 |
C5—C6—H6 | 119 | C12—N15—C17 | 119 (5) |
N1—C6—H6 | 119 | C12—N15—C16 | 119 (5) |
C4—C7—H7 | 119 | C16—N15—C17 | 121 (5) |
C4—C7—C8 | 123 (6) | N15—C16—H16C | 110 |
C8—C7—H7 | 118 | N15—C16—H16B | 110 |
C7—C8—H8 | 118 | N15—C16—H16A | 110 |
C7—C8—C9 | 123 (6) | N15—C17—H17C | 109 |
C9—C8—H8 | 118 | N15—C17—H17B | 109 |
C8—C9—C14 | 120 (6) | N15—C17—H17A | 109 |
C8—C9—C10 | 120 (5) |
Experimental details
Crystal data | |
Chemical formula | C15H16N2O |
Mr | 240.2 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 26.822 (4), 7.758 (2), 6.079 (3) |
β (°) | 94.03 (1) |
V (Å3) | 1262 (1) |
Z | 4 |
Radiation type | Cu Kα1, λ = 1.54056 Å |
Specimen shape, size (mm) | Flat_sheet, 20 × 20 |
Data collection | |
Diffractometer | Philips Analytical XPert PRO X-ray diffraction system diffractometer |
Specimen mounting | The powder was sprinkled on the sample holder through a fine sieve. The thickness of the layer was no more than 0.1 mm. |
Data collection mode | Reflection |
Scan method | Step |
2θ values (°) | 2θmin = 6 2θmax = 60 2θstep = 0.01 |
Refinement | |
R factors and goodness of fit | Rp = 0.19, Rwp = 0.29, Rexp = 0.19, χ2 = 2.250 |
No. of data points | 5401 |
No. of parameters | 162 |
No. of restraints | 112 |
H-atom treatment | H-atom parameters constrained |
Computer programs: local program, MRIA (Zlokazov & Chernyshev, 1992), MRIA and PARST (Nardelli, 1983).
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4-(4'-Dimethylaminostyril)pyridine N-oxide, (I), is an unusual substance. It has two potential coordinating groups, N–O and NMe2, which are conjugated with each other through an extensive π-system. The question of the first site of protonation has been discussed previously (Titski et al., 1996; Korzhenevskaya & Rybatschenko, 1999). This compound is the subject of much research devoted to the investigation of complexes formed with Lewis acids (Andreev et al., 2002), intramolecular charge transfer (Andreev et al., 1998), nucleophilic properties (Rybatschenko et al., 2001; Lobanova, 2001), and biological activity (Anisimov et al., 2000). Compound (I) has apoptogenic and erythroid differentiation induction activity towards K-562 cells (Volkova et al., 2001). According to our data, the molecule of (I) studied here is the trans isomer. The IR spectrum contains a band at 970 cm−1, which shows the presence of a trans H—C═C—H group. The NMR spectrum contains two signals for vicinal olefin protons with J = 16 Hz, characteristic of a trans isomer (Silverstein et al., 1977).