Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024385/wn2143sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024385/wn2143Isup2.hkl |
CCDC reference: 651533
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.134
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.53 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Allen et al. (1987); Desiraju & Steiner (1999); Dimmock et al. (2001); Jia et al. (1989); Nesterov (2004); Nesterov et al. (2003, 2007); Rowland & Taylor (1996); Sarkisov et al. (2005).
The title compound was obtained according to literature procedures (Jia et al., 1989; Nesterov et al., 2003) by the reaction of p-dimethylaminobenzaldehyde with 1-propyl-4-piperidone. The precipitate was isolated and recrystallized from ethanol/tetrahydrofuran (1:1) (melting point 464 K, yield 76%). Crystals were obtained by isothermic evaporation of an ethanolic solution. The structure of the compound was characterized by 1H and 13C NMR spectroscopy.
All H atoms were placed in geometrically calculated positions and refined using a riding model with C—H distances of 0.95 Å for Csp2, with Uiso(H) = 1.2Ueq(C); 0.99 Å for CH2, with Uiso (H) = 1.2Ueq(C); 0.98 Å for CH3, with Uiso(H) = 1.5Ueq(C).
As a continuation of our work that includes synthesis and structural investigations of nonlinear optical organic compounds with two-photon absorption properties and potential as biophotonic materials (Nesterov et al., 2003; Nesterov, 2004; Sarkisov et al., 2005; Nesterov et al., 2007), we have investigated the structure of the title compound that has a general motif D-π-A-π-D (Scheme). This compound may find application as an agent for locating cancer cells with two-photon excited fluorescence and as a potential agent for a photodynamic treatment of cancer (Nesterov et al., 2003; Sarkisov et al., 2005).
The title compound belongs to a group that has shown anticancer activity (Dimmock et al., 2001) and here we describe its structure (Fig. 1). The central heterocycle adopts a flattened boat conformation; atoms N1 and C4 lie 0.699 (2) and 0.118 (2) Å, respectively, out of the C2/C3/C5/C6 plane [planar within 0.023 (2) Å]. Dihedral angles between the planar part of the heterocycle and two almost flat fragments that include the benzene rings and attached C atoms are 17.1 (1) and 14.8 (1)° for C7—C13 and C14—C20, respectively. This might be partly due to the presence in the molecule of short intramolecular contacts H2B···H13A and H6A···H20A with distances 2.06 and 2.18 Å, respectively, that are somewhat shorter than the sum of the van der Waals radii (2.2 Å) of the hydrogen atoms (Rowland & Taylor, 1996).
Atom N1 in the piperidone ring is pyramidal, with the sum of bond angles equal to 328.0°; the propyl substituent attached to it occupies the equatorial position. Bond length distributions in the π-conjugated bridges and p-dimethylaminophenyl fragments definitely show an alternation of single C—C and double C═C bond lengths (Table) and close to the standard conjugated values (Allen et al., 1987). In the crystal structure, there are weak intermolecular C—H···O contacts that can be considered as weak hydrogen bonds (Desiraju & Steiner, 1999). Such weak hydrogen bonds link the molecules into ribbons along the b axis (Fig. 2).
For related literature, see: Allen et al. (1987); Desiraju & Steiner (1999); Dimmock et al. (2001); Jia et al. (1989); Nesterov (2004); Nesterov et al. (2003, 2007); Rowland & Taylor (1996); Sarkisov et al. (2005).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2001); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.
C26H33N3O | F(000) = 872 |
Mr = 403.55 | Dx = 1.223 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.7200 (9) Å | Cell parameters from 117 reflections |
b = 6.1434 (4) Å | θ = 4–24° |
c = 24.2503 (16) Å | µ = 0.08 mm−1 |
β = 92.262 (1)° | T = 100 K |
V = 2191.3 (2) Å3 | Needle, yellow |
Z = 4 | 0.12 × 0.04 × 0.04 mm |
Bruker SMART APEX II CCD area-detector diffractometer | 4296 independent reflections |
Radiation source: fine-focus sealed tube | 2976 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
φ and ω scans | θmax = 26.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −18→18 |
Tmin = 0.912, Tmax = 0.997 | k = −7→7 |
18187 measured reflections | l = −29→29 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.060P)2 + 1.P] where P = (Fo2 + 2Fc2)/3 |
4296 reflections | (Δ/σ)max < 0.001 |
276 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C26H33N3O | V = 2191.3 (2) Å3 |
Mr = 403.55 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.7200 (9) Å | µ = 0.08 mm−1 |
b = 6.1434 (4) Å | T = 100 K |
c = 24.2503 (16) Å | 0.12 × 0.04 × 0.04 mm |
β = 92.262 (1)° |
Bruker SMART APEX II CCD area-detector diffractometer | 4296 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 2976 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 0.997 | Rint = 0.057 |
18187 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.57 e Å−3 |
4296 reflections | Δρmin = −0.23 e Å−3 |
276 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.24493 (10) | 0.9379 (2) | 0.58185 (6) | 0.0272 (4) | |
N1 | 0.36050 (11) | 0.4318 (3) | 0.50843 (7) | 0.0226 (4) | |
N2 | −0.13269 (12) | 0.4966 (3) | 0.34015 (7) | 0.0271 (4) | |
N3 | 0.66819 (13) | 0.5195 (3) | 0.79613 (7) | 0.0294 (4) | |
C1 | 0.40071 (15) | 0.2306 (4) | 0.48621 (9) | 0.0292 (5) | |
H1A | 0.3783 | 0.1047 | 0.5073 | 0.035* | |
H1B | 0.4675 | 0.2372 | 0.4925 | 0.035* | |
C2 | 0.26123 (13) | 0.4304 (3) | 0.50017 (9) | 0.0230 (5) | |
H2A | 0.2355 | 0.3067 | 0.5205 | 0.028* | |
H2B | 0.2450 | 0.4110 | 0.4605 | 0.028* | |
C3 | 0.22117 (13) | 0.6403 (3) | 0.52019 (8) | 0.0201 (4) | |
C4 | 0.26981 (14) | 0.7562 (3) | 0.56591 (8) | 0.0215 (5) | |
C5 | 0.34805 (13) | 0.6429 (3) | 0.59400 (8) | 0.0205 (4) | |
C6 | 0.38466 (14) | 0.4402 (3) | 0.56754 (8) | 0.0225 (5) | |
H6A | 0.4517 | 0.4370 | 0.5729 | 0.027* | |
H6B | 0.3598 | 0.3102 | 0.5858 | 0.027* | |
C7 | 0.14321 (13) | 0.7289 (3) | 0.49991 (8) | 0.0206 (4) | |
H7A | 0.1292 | 0.8655 | 0.5159 | 0.025* | |
C8 | 0.07633 (13) | 0.6557 (3) | 0.45827 (8) | 0.0201 (4) | |
C9 | 0.01067 (14) | 0.8070 (3) | 0.43939 (8) | 0.0239 (5) | |
H9A | 0.0135 | 0.9506 | 0.4539 | 0.029* | |
C10 | −0.05739 (14) | 0.7584 (3) | 0.40107 (9) | 0.0242 (5) | |
H10A | −0.1000 | 0.8676 | 0.3900 | 0.029* | |
C11 | −0.06472 (14) | 0.5473 (3) | 0.37789 (8) | 0.0216 (4) | |
C12 | 0.00081 (13) | 0.3930 (3) | 0.39659 (8) | 0.0214 (5) | |
H12A | −0.0014 | 0.2498 | 0.3818 | 0.026* | |
C13 | 0.06775 (13) | 0.4452 (3) | 0.43573 (8) | 0.0209 (4) | |
H13A | 0.1094 | 0.3356 | 0.4479 | 0.025* | |
C14 | 0.37999 (13) | 0.7282 (3) | 0.64231 (9) | 0.0226 (5) | |
H14A | 0.3499 | 0.8577 | 0.6527 | 0.027* | |
C15 | 0.45150 (13) | 0.6596 (3) | 0.68130 (8) | 0.0214 (4) | |
C16 | 0.48335 (14) | 0.8106 (3) | 0.72105 (9) | 0.0255 (5) | |
H16A | 0.4554 | 0.9499 | 0.7218 | 0.031* | |
C17 | 0.55279 (15) | 0.7671 (3) | 0.75880 (9) | 0.0266 (5) | |
H17A | 0.5720 | 0.8763 | 0.7844 | 0.032* | |
C18 | 0.59610 (14) | 0.5619 (3) | 0.76001 (8) | 0.0234 (5) | |
C19 | 0.56228 (14) | 0.4060 (3) | 0.72189 (8) | 0.0235 (5) | |
H19A | 0.5880 | 0.2641 | 0.7223 | 0.028* | |
C20 | 0.49298 (14) | 0.4537 (3) | 0.68410 (8) | 0.0239 (5) | |
H20A | 0.4725 | 0.3437 | 0.6590 | 0.029* | |
C21 | −0.19772 (15) | 0.6606 (4) | 0.32053 (9) | 0.0290 (5) | |
H21A | −0.2211 | 0.7395 | 0.3521 | 0.044* | |
H21B | −0.2482 | 0.5895 | 0.3001 | 0.044* | |
H21C | −0.1676 | 0.7629 | 0.2962 | 0.044* | |
C22 | −0.13508 (15) | 0.2850 (3) | 0.31302 (9) | 0.0274 (5) | |
H22A | −0.0746 | 0.2506 | 0.2999 | 0.041* | |
H22B | −0.1791 | 0.2887 | 0.2817 | 0.041* | |
H22C | −0.1531 | 0.1733 | 0.3393 | 0.041* | |
C23 | 0.69416 (16) | 0.6790 (4) | 0.83827 (10) | 0.0354 (6) | |
H23A | 0.7150 | 0.8123 | 0.8206 | 0.053* | |
H23B | 0.7433 | 0.6197 | 0.8622 | 0.053* | |
H23C | 0.6416 | 0.7123 | 0.8604 | 0.053* | |
C24 | 0.70289 (16) | 0.3012 (4) | 0.80339 (9) | 0.0304 (5) | |
H24A | 0.7107 | 0.2344 | 0.7672 | 0.046* | |
H24B | 0.6599 | 0.2148 | 0.8241 | 0.046* | |
H24D | 0.7616 | 0.3063 | 0.8238 | 0.046* | |
C25 | 0.38018 (16) | 0.1914 (4) | 0.42620 (9) | 0.0323 (6) | |
H25A | 0.4025 | 0.3158 | 0.4046 | 0.039* | |
H25C | 0.3136 | 0.1808 | 0.4194 | 0.039* | |
C26 | 0.42548 (16) | −0.0191 (4) | 0.40712 (10) | 0.0335 (6) | |
H26D | 0.4099 | −0.0436 | 0.3680 | 0.050* | |
H26A | 0.4039 | −0.1420 | 0.4288 | 0.050* | |
H26B | 0.4916 | −0.0062 | 0.4124 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0317 (8) | 0.0175 (7) | 0.0320 (8) | 0.0061 (6) | −0.0055 (7) | −0.0053 (6) |
N1 | 0.0213 (9) | 0.0218 (9) | 0.0244 (9) | 0.0036 (7) | −0.0033 (7) | −0.0061 (7) |
N2 | 0.0326 (10) | 0.0173 (9) | 0.0303 (10) | 0.0027 (8) | −0.0105 (8) | −0.0004 (8) |
N3 | 0.0348 (11) | 0.0213 (10) | 0.0311 (10) | 0.0020 (8) | −0.0116 (8) | −0.0021 (8) |
C1 | 0.0250 (11) | 0.0277 (12) | 0.0348 (13) | 0.0076 (10) | −0.0027 (10) | −0.0095 (10) |
C2 | 0.0243 (11) | 0.0174 (10) | 0.0271 (11) | 0.0020 (9) | −0.0021 (9) | −0.0061 (9) |
C3 | 0.0226 (10) | 0.0156 (10) | 0.0220 (11) | 0.0004 (8) | 0.0022 (8) | 0.0008 (8) |
C4 | 0.0254 (11) | 0.0145 (10) | 0.0249 (11) | 0.0009 (9) | 0.0035 (9) | −0.0017 (8) |
C5 | 0.0201 (10) | 0.0167 (10) | 0.0248 (11) | 0.0003 (8) | 0.0007 (8) | −0.0004 (8) |
C6 | 0.0224 (11) | 0.0178 (10) | 0.0271 (11) | 0.0046 (8) | −0.0036 (9) | −0.0025 (9) |
C7 | 0.0252 (11) | 0.0157 (10) | 0.0211 (10) | 0.0020 (8) | 0.0017 (8) | 0.0007 (8) |
C8 | 0.0210 (10) | 0.0178 (10) | 0.0216 (11) | 0.0004 (8) | 0.0014 (8) | 0.0017 (8) |
C9 | 0.0298 (12) | 0.0176 (10) | 0.0241 (11) | 0.0039 (9) | −0.0009 (9) | −0.0015 (9) |
C10 | 0.0275 (11) | 0.0176 (10) | 0.0271 (12) | 0.0060 (9) | −0.0034 (9) | 0.0021 (9) |
C11 | 0.0261 (11) | 0.0181 (10) | 0.0203 (10) | −0.0007 (8) | −0.0007 (9) | 0.0021 (8) |
C12 | 0.0256 (11) | 0.0141 (10) | 0.0244 (11) | 0.0004 (8) | 0.0004 (9) | 0.0002 (8) |
C13 | 0.0219 (10) | 0.0151 (10) | 0.0256 (11) | 0.0043 (8) | 0.0007 (8) | 0.0033 (8) |
C14 | 0.0228 (11) | 0.0165 (10) | 0.0284 (12) | 0.0027 (8) | 0.0021 (9) | −0.0029 (9) |
C15 | 0.0221 (11) | 0.0199 (10) | 0.0221 (11) | 0.0012 (8) | −0.0005 (8) | −0.0020 (9) |
C16 | 0.0287 (11) | 0.0185 (11) | 0.0290 (12) | 0.0040 (9) | −0.0019 (9) | −0.0064 (9) |
C17 | 0.0311 (12) | 0.0221 (11) | 0.0262 (12) | 0.0005 (9) | −0.0030 (9) | −0.0078 (9) |
C18 | 0.0251 (11) | 0.0228 (11) | 0.0221 (11) | 0.0009 (9) | −0.0004 (9) | 0.0014 (9) |
C19 | 0.0289 (11) | 0.0157 (10) | 0.0257 (11) | 0.0024 (9) | −0.0015 (9) | −0.0012 (9) |
C20 | 0.0304 (12) | 0.0174 (10) | 0.0236 (11) | −0.0001 (9) | −0.0012 (9) | −0.0046 (9) |
C21 | 0.0317 (12) | 0.0239 (11) | 0.0306 (12) | 0.0040 (10) | −0.0100 (10) | 0.0015 (10) |
C22 | 0.0327 (12) | 0.0203 (11) | 0.0287 (12) | −0.0001 (9) | −0.0055 (9) | −0.0031 (9) |
C23 | 0.0370 (13) | 0.0356 (14) | 0.0324 (13) | 0.0049 (11) | −0.0124 (11) | −0.0076 (11) |
C24 | 0.0329 (13) | 0.0285 (12) | 0.0292 (12) | 0.0070 (10) | −0.0074 (10) | −0.0004 (10) |
C25 | 0.0316 (12) | 0.0320 (13) | 0.0331 (13) | 0.0069 (10) | −0.0015 (10) | −0.0062 (10) |
C26 | 0.0306 (12) | 0.0339 (13) | 0.0356 (13) | 0.0070 (10) | −0.0029 (10) | −0.0150 (11) |
O1—C4 | 1.242 (2) | C12—H12A | 0.9500 |
N1—C6 | 1.464 (3) | C13—H13A | 0.9500 |
N1—C2 | 1.467 (3) | C14—C15 | 1.449 (3) |
N1—C1 | 1.481 (3) | C14—H14A | 0.9500 |
N2—C11 | 1.365 (3) | C15—C16 | 1.405 (3) |
N2—C21 | 1.456 (3) | C15—C20 | 1.405 (3) |
N2—C22 | 1.457 (3) | C16—C17 | 1.371 (3) |
N3—C18 | 1.374 (3) | C16—H16A | 0.9500 |
N3—C24 | 1.443 (3) | C17—C18 | 1.412 (3) |
N3—C23 | 1.456 (3) | C17—H17A | 0.9500 |
C1—C25 | 1.494 (3) | C18—C19 | 1.409 (3) |
C1—H1A | 0.9900 | C19—C20 | 1.376 (3) |
C1—H1B | 0.9900 | C19—H19A | 0.9500 |
C2—C3 | 1.506 (3) | C20—H20A | 0.9500 |
C2—H2A | 0.9900 | C21—H21A | 0.9800 |
C2—H2B | 0.9900 | C21—H21B | 0.9800 |
C3—C7 | 1.346 (3) | C21—H21C | 0.9800 |
C3—C4 | 1.478 (3) | C22—H22A | 0.9800 |
C4—C5 | 1.487 (3) | C22—H22B | 0.9800 |
C5—C14 | 1.351 (3) | C22—H22C | 0.9800 |
C5—C6 | 1.510 (3) | C23—H23A | 0.9800 |
C6—H6A | 0.9900 | C23—H23B | 0.9800 |
C6—H6B | 0.9900 | C23—H23C | 0.9800 |
C7—C8 | 1.453 (3) | C24—H24A | 0.9800 |
C7—H7A | 0.9500 | C24—H24B | 0.9800 |
C8—C9 | 1.405 (3) | C24—H24D | 0.9800 |
C8—C13 | 1.408 (3) | C25—C26 | 1.535 (3) |
C9—C10 | 1.372 (3) | C25—H25A | 0.9900 |
C9—H9A | 0.9500 | C25—H25C | 0.9900 |
C10—C11 | 1.416 (3) | C26—H26D | 0.9800 |
C10—H10A | 0.9500 | C26—H26A | 0.9800 |
C11—C12 | 1.414 (3) | C26—H26B | 0.9800 |
C12—C13 | 1.379 (3) | ||
C6—N1—C2 | 109.64 (16) | C5—C14—C15 | 132.23 (19) |
C6—N1—C1 | 107.48 (16) | C5—C14—H14A | 113.9 |
C2—N1—C1 | 110.84 (16) | C15—C14—H14A | 113.9 |
C11—N2—C21 | 121.08 (17) | C16—C15—C20 | 115.38 (18) |
C11—N2—C22 | 120.68 (17) | C16—C15—C14 | 118.03 (18) |
C21—N2—C22 | 117.76 (17) | C20—C15—C14 | 126.60 (19) |
C18—N3—C24 | 121.00 (18) | C17—C16—C15 | 123.31 (19) |
C18—N3—C23 | 119.62 (18) | C17—C16—H16A | 118.3 |
C24—N3—C23 | 117.24 (17) | C15—C16—H16A | 118.3 |
N1—C1—C25 | 114.85 (18) | C16—C17—C18 | 120.78 (19) |
N1—C1—H1A | 108.6 | C16—C17—H17A | 119.6 |
C25—C1—H1A | 108.6 | C18—C17—H17A | 119.6 |
N1—C1—H1B | 108.6 | N3—C18—C19 | 122.22 (19) |
C25—C1—H1B | 108.6 | N3—C18—C17 | 121.29 (19) |
H1A—C1—H1B | 107.5 | C19—C18—C17 | 116.48 (18) |
N1—C2—C3 | 110.58 (16) | C20—C19—C18 | 121.71 (19) |
N1—C2—H2A | 109.5 | C20—C19—H19A | 119.1 |
C3—C2—H2A | 109.5 | C18—C19—H19A | 119.1 |
N1—C2—H2B | 109.5 | C19—C20—C15 | 122.25 (19) |
C3—C2—H2B | 109.5 | C19—C20—H20A | 118.9 |
H2A—C2—H2B | 108.1 | C15—C20—H20A | 118.9 |
C7—C3—C4 | 117.38 (18) | N2—C21—H21A | 109.5 |
C7—C3—C2 | 124.58 (18) | N2—C21—H21B | 109.5 |
C4—C3—C2 | 118.03 (17) | H21A—C21—H21B | 109.5 |
O1—C4—C3 | 121.77 (18) | N2—C21—H21C | 109.5 |
O1—C4—C5 | 120.70 (18) | H21A—C21—H21C | 109.5 |
C3—C4—C5 | 117.48 (17) | H21B—C21—H21C | 109.5 |
C14—C5—C4 | 116.91 (18) | N2—C22—H22A | 109.5 |
C14—C5—C6 | 124.78 (18) | N2—C22—H22B | 109.5 |
C4—C5—C6 | 118.29 (17) | H22A—C22—H22B | 109.5 |
N1—C6—C5 | 111.59 (16) | N2—C22—H22C | 109.5 |
N1—C6—H6A | 109.3 | H22A—C22—H22C | 109.5 |
C5—C6—H6A | 109.3 | H22B—C22—H22C | 109.5 |
N1—C6—H6B | 109.3 | N3—C23—H23A | 109.5 |
C5—C6—H6B | 109.3 | N3—C23—H23B | 109.5 |
H6A—C6—H6B | 108.0 | H23A—C23—H23B | 109.5 |
C3—C7—C8 | 132.31 (19) | N3—C23—H23C | 109.5 |
C3—C7—H7A | 113.8 | H23A—C23—H23C | 109.5 |
C8—C7—H7A | 113.8 | H23B—C23—H23C | 109.5 |
C9—C8—C13 | 115.55 (18) | N3—C24—H24A | 109.5 |
C9—C8—C7 | 117.40 (18) | N3—C24—H24B | 109.5 |
C13—C8—C7 | 127.00 (18) | H24A—C24—H24B | 109.5 |
C10—C9—C8 | 123.47 (19) | N3—C24—H24D | 109.5 |
C10—C9—H9A | 118.3 | H24A—C24—H24D | 109.5 |
C8—C9—H9A | 118.3 | H24B—C24—H24D | 109.5 |
C9—C10—C11 | 120.68 (19) | C1—C25—C26 | 110.83 (19) |
C9—C10—H10A | 119.7 | C1—C25—H25A | 109.5 |
C11—C10—H10A | 119.7 | C26—C25—H25A | 109.5 |
N2—C11—C12 | 122.34 (18) | C1—C25—H25C | 109.5 |
N2—C11—C10 | 121.15 (18) | C26—C25—H25C | 109.5 |
C12—C11—C10 | 116.50 (18) | H25A—C25—H25C | 108.1 |
C13—C12—C11 | 121.67 (18) | C25—C26—H26D | 109.5 |
C13—C12—H12A | 119.2 | C25—C26—H26A | 109.5 |
C11—C12—H12A | 119.2 | H26D—C26—H26A | 109.5 |
C12—C13—C8 | 122.10 (18) | C25—C26—H26B | 109.5 |
C12—C13—H13A | 118.9 | H26D—C26—H26B | 109.5 |
C8—C13—H13A | 118.9 | H26A—C26—H26B | 109.5 |
C6—N1—C1—C25 | 178.10 (19) | C22—N2—C11—C10 | 174.65 (19) |
C2—N1—C1—C25 | 58.3 (2) | C9—C10—C11—N2 | 179.3 (2) |
C6—N1—C2—C3 | 64.4 (2) | C9—C10—C11—C12 | 0.3 (3) |
C1—N1—C2—C3 | −177.10 (17) | N2—C11—C12—C13 | −178.40 (19) |
N1—C2—C3—C7 | 151.68 (19) | C10—C11—C12—C13 | 0.6 (3) |
N1—C2—C3—C4 | −29.3 (2) | C11—C12—C13—C8 | −1.7 (3) |
C7—C3—C4—O1 | −6.5 (3) | C9—C8—C13—C12 | 1.7 (3) |
C2—C3—C4—O1 | 174.41 (19) | C7—C8—C13—C12 | 179.35 (19) |
C7—C3—C4—C5 | 171.03 (18) | C4—C5—C14—C15 | 177.6 (2) |
C2—C3—C4—C5 | −8.1 (3) | C6—C5—C14—C15 | −1.0 (4) |
O1—C4—C5—C14 | 10.8 (3) | C5—C14—C15—C16 | 164.8 (2) |
C3—C4—C5—C14 | −166.72 (18) | C5—C14—C15—C20 | −15.8 (4) |
O1—C4—C5—C6 | −170.44 (19) | C20—C15—C16—C17 | 2.8 (3) |
C3—C4—C5—C6 | 12.0 (3) | C14—C15—C16—C17 | −177.7 (2) |
C2—N1—C6—C5 | −60.5 (2) | C15—C16—C17—C18 | −0.8 (3) |
C1—N1—C6—C5 | 178.94 (17) | C24—N3—C18—C19 | −10.8 (3) |
C14—C5—C6—N1 | −159.57 (19) | C23—N3—C18—C19 | −173.8 (2) |
C4—C5—C6—N1 | 21.8 (3) | C24—N3—C18—C17 | 170.1 (2) |
C4—C3—C7—C8 | −175.9 (2) | C23—N3—C18—C17 | 7.1 (3) |
C2—C3—C7—C8 | 3.1 (4) | C16—C17—C18—N3 | 177.3 (2) |
C3—C7—C8—C9 | −168.4 (2) | C16—C17—C18—C19 | −1.8 (3) |
C3—C7—C8—C13 | 14.0 (4) | N3—C18—C19—C20 | −176.8 (2) |
C13—C8—C9—C10 | −0.8 (3) | C17—C18—C19—C20 | 2.4 (3) |
C7—C8—C9—C10 | −178.65 (19) | C18—C19—C20—C15 | −0.3 (3) |
C8—C9—C10—C11 | −0.2 (3) | C16—C15—C20—C19 | −2.3 (3) |
C21—N2—C11—C12 | −178.29 (19) | C14—C15—C20—C19 | 178.3 (2) |
C22—N2—C11—C12 | −6.4 (3) | N1—C1—C25—C26 | 179.46 (19) |
C21—N2—C11—C10 | 2.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O1i | 0.95 | 2.56 | 3.371 (3) | 143 |
C22—H22C···O1ii | 0.98 | 2.48 | 3.364 (3) | 150 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C26H33N3O |
Mr | 403.55 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 14.7200 (9), 6.1434 (4), 24.2503 (16) |
β (°) | 92.262 (1) |
V (Å3) | 2191.3 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.12 × 0.04 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART APEX II CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.912, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18187, 4296, 2976 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.134, 1.01 |
No. of reflections | 4296 |
No. of parameters | 276 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.57, −0.23 |
Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXTL-NT (Sheldrick, 2001), SHELXTL-NT.
O1—C4 | 1.242 (2) | C5—C14 | 1.351 (3) |
N2—C11 | 1.365 (3) | C7—C8 | 1.453 (3) |
N3—C18 | 1.374 (3) | C14—C15 | 1.449 (3) |
C3—C7 | 1.346 (3) | ||
C4—C3—C7—C8 | −175.9 (2) | C4—C5—C14—C15 | 177.6 (2) |
C3—C7—C8—C9 | −168.4 (2) | C5—C14—C15—C16 | 164.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O1i | 0.95 | 2.56 | 3.371 (3) | 143 |
C22—H22C···O1ii | 0.98 | 2.48 | 3.364 (3) | 150 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+1. |
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As a continuation of our work that includes synthesis and structural investigations of nonlinear optical organic compounds with two-photon absorption properties and potential as biophotonic materials (Nesterov et al., 2003; Nesterov, 2004; Sarkisov et al., 2005; Nesterov et al., 2007), we have investigated the structure of the title compound that has a general motif D-π-A-π-D (Scheme). This compound may find application as an agent for locating cancer cells with two-photon excited fluorescence and as a potential agent for a photodynamic treatment of cancer (Nesterov et al., 2003; Sarkisov et al., 2005).
The title compound belongs to a group that has shown anticancer activity (Dimmock et al., 2001) and here we describe its structure (Fig. 1). The central heterocycle adopts a flattened boat conformation; atoms N1 and C4 lie 0.699 (2) and 0.118 (2) Å, respectively, out of the C2/C3/C5/C6 plane [planar within 0.023 (2) Å]. Dihedral angles between the planar part of the heterocycle and two almost flat fragments that include the benzene rings and attached C atoms are 17.1 (1) and 14.8 (1)° for C7—C13 and C14—C20, respectively. This might be partly due to the presence in the molecule of short intramolecular contacts H2B···H13A and H6A···H20A with distances 2.06 and 2.18 Å, respectively, that are somewhat shorter than the sum of the van der Waals radii (2.2 Å) of the hydrogen atoms (Rowland & Taylor, 1996).
Atom N1 in the piperidone ring is pyramidal, with the sum of bond angles equal to 328.0°; the propyl substituent attached to it occupies the equatorial position. Bond length distributions in the π-conjugated bridges and p-dimethylaminophenyl fragments definitely show an alternation of single C—C and double C═C bond lengths (Table) and close to the standard conjugated values (Allen et al., 1987). In the crystal structure, there are weak intermolecular C—H···O contacts that can be considered as weak hydrogen bonds (Desiraju & Steiner, 1999). Such weak hydrogen bonds link the molecules into ribbons along the b axis (Fig. 2).