research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 75| Part 11| November 2019| Pages 1595-1599
https://doi.org/10.1107/S205698901901329X

Crystal structures, syntheses, and spectroscopic and electrochemical measurements of two push–pull chromophores: 2-[4-(di­methyl­amino)­benzyl­­idene]-1H-indene-1,3(2H)-dione and (E)-2-{3-[4-(di­meth­ylamino)­phen­yl]allyl­­idene}-1H-indene-1,3(2H)-dione

CROSSMARK_Color_square_no_text.svg
Georgii Bogdanov,a* John P. Tillotsonb and Tatiana Timofeevaa

aDepartment of Chemistry, New Mexico Highlands University, Las Vegas, New Mexico, 87701, USA, and bSchool of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia, 30332, USA
*Correspondence e-mail: bogdgv@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 30 August 2019; accepted 27 September 2019; online 3 October 2019)

The title pull–push chromophores, 2-[4-(di­methyl­amino)­benzyl­idene]-1H-indene-1,3(2H)-dione, C18H15NO2 (ID[1]) and (E)-2-{3-[4-(di­methyl­amino)­phen­yl]allyl­idene}-1H-indene-1,3(2H)-dione, C20H17NO2 (ID[2]), have donor–π-bridge–acceptor structures. The mol­ecule with the short π-bridge, ID[1], is almost planar while for the mol­ecule with a longer bridge, ID[2], is less planar. The benzene ring is inclined to the mean plane of the 2,3-di­hydro-1H-indene unit by 3.19 (4)° in ID[1] and 13.06 (8)° in ID[2]. The structures of three polymorphs of compound ID[1] have been reported: the α-polymorph [space group P21/c; Magomedova & Zvonkova (1978[Magomedova, N. S. & Zvonkova, Z. V. (1978). Kristallografiya, 23, 281-288.]). Kristallografiya, 23, 281–288], the β-polymorph [space group P21/c; Magomedova & Zvonkova (1980[Magomedova, N. S. & Zvonkova, Z. V. (1980). Kristallografiya, 25, 1183-1187.]). Kristallografiya, 25 1183–1187] and the γ-polymorph [space group Pna21; Magomedova, Neigauz, Zvonkova & Novakovskaya (1980[Magomedova, N. S., Neigauz, M. G., Zvonkova, Z. V. & Novakovskaya, L. A. (1980). Kristallografiya, 25, 400-402.]). Kristallografiya, 25, 400–402]. The mol­ecular packing in ID[1] studied here is centrosymmetric (space group P21/c) and corresponds to the β-polymorph structure. The mol­ecular packing in ID[2] is non-centrosymmetric (space group P21), which suggests potential NLO properties for this crystalline material. In both compounds, there is short intra­molecular C—H⋯O contact present, enclosing an S(7) ring motif. In the crystal of ID[1], mol­ecules are linked by C—H⋯O hydrogen bonds and C—H⋯π inter­actions, forming layers parallel to the bc plane. In the crystal of ID[2], mol­ecules are liked by C—H⋯O hydrogen bonds to form 21 helices propagating along the b-axis direction. The mol­ecules in the helix are linked by offset π–π inter­actions with, for example, a centroid–centroid distance of 3.9664 (13) Å (= b axis) separating the indene rings, and an offset of 1.869 Å. Spectroscopic and electrochemical measurements show the ability of these compounds to easily transfer electrons through the π-conjugated chain.

CCDC references: 1956419; 1956418; 1956418; 1956419

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1. Chemical context

Organic mol­ecules containing donor and acceptor groups connected by a conjugated π-bridge (push–pull chromophores) are important in many areas of materials chemistry, especially organic electronics and optoelectronics. Applic­ations of pull–push mol­ecules can be related to their properties such as intra­molecular charge transfer and specific mol­ecular arrangements in the solid state. Intra­molecular charge transfer from donor to acceptor via a π-bridge defines their colour, light absorption and emission, hyperpolarizability and other optoelectronic effects. Applications of pull–push chromophores include non-linear optics (NLO; Ortiz et al., 1994[Ortiz, R., Marder, S. R., Cheng, L.-T., Tiemann, B. G., Cavagnero, S. & Ziller, J. W. (1994). J. Chem. Soc. Chem. Commun. pp. 2263-2264.]), as luminescent sensors (Duarte et al., 2011[Duarte, A., Pu, K.-Y., Liu, B. & Bazan, G. C. (2011). Chem. Mater. 23, 501-515.]; Qin et al., 2015[Qin, W., Lam, J. W., Yang, Z., Chen, S., Liang, G., Zhao, W., Kwok, H. S. & Tang, B. Z. (2015). Chem. Commun. 51, 7321-7324.]), solid-state lasers (Samuel & Turnbull, 2007[Samuel, I. D. & Turnbull, G. A. (2007). Chem. Rev. 107, 1272-1295.]), organic light-emitting diodes (Muller et al., 2003[Müller, C. D., Falcou, A., Reckefuss, N., Rojahn, M., Wiederhirn, V., Rudati, P., Frohne, H., Nuyken, O., Becker, H. & Meerholz, K. (2003). Nature, 421, 829-833.]), organic field-effect transistors (Suponitsky et al., 2006[Suponitsky, K. Y., Timofeeva, T. V. & Antipin, M. Y. (2006). Russ. Chem. Rev. 75, 457-496.]; Oliveira et al., 2018[Oliveira, A. F. C. D. S., de Souza, A. P. M., de Oliveira, A. S., da Silva, M. L., de Oliveira, F. M., Santos, E. G., da Silva, Í. E. P., Ferreira, R. S., Villela, F. S., Martins, F. T., Leal, D. H. S., Vaz, B. G., Teixeira, R. R. & de Paula, S. O. (2018). Eur. J. Med. Chem. 149, 98-109.]) and many more. The spectroscopic properties of pull–push mol­ecules are related to the donor and acceptor strength in these mol­ecules and to the length of the π-bridge. Many such compounds have been studied, but not all of their crystal structures have been reported. Such compounds are important for their NLO properties (Andreu et al., 2003[Andreu, R., Garín, J., Orduna, J., Alcalá, R. & Villacampa, B. (2003). Org. Lett. 5, 3143-3146.]; Raimundo et al., 2002[Raimundo, J.-M., Blanchard, P., Gallego-Planas, N., Mercier, N., Ledoux-Rak, I., Hierle, R. & Roncali, J. (2002). J. Org. Chem. 67, 205-218.]). Herein, we report on the crystal structures, syntheses and spectroscopic and electrochemical properties of the title donor–π-bridge–acceptor structures, ID[1] and ID[2]. The structures of three polymorphs of ID[1] have been reported previously; the α-polymorph (Magomedova & Zvonkova, 1978[Magomedova, N. S. & Zvonkova, Z. V. (1978). Kristallografiya, 23, 281-288.]), the β-polymorph (Magomedova & Zvonkova, 1980[Magomedova, N. S. & Zvonkova, Z. V. (1980). Kristallografiya, 25, 1183-1187.]) and the γ-polymorph (Magomedova, Neigauz et al., 1980[Magomedova, N. S., Neigauz, M. G., Zvonkova, Z. V. & Novakovskaya, L. A. (1980). Kristallografiya, 25, 400-402.]). We have repeated the structural study of ID[1] in order to establish exactly which polymorph we obtained. It was then characterized by spectroscopic and electrochemical measurements.

[Scheme 1]

2. Structural commentary

The mol­ecular structures of ID[1] and ID[2] are illustrated in Fig. 1[link]. The structural analysis of ID[1] synthesized by us established that it is the β-polymorph (Magomedova & Zvonkova, 1980[Magomedova, N. S. & Zvonkova, Z. V. (1980). Kristallografiya, 25, 1183-1187.]), and it was then characterized with spectroscopic (§4) and electrochemical (§5) measurements.

[Figure 1]
Figure 1
A view of the mol­ecular structure of the title compounds, (a) ID[1] and (b) ID[2], with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intra­molecular C—H⋯O hydrogen bonds (Tables 2[link] and 3[link]) are shown as dashed lines.

Both mol­ecules have acceptor–π-bridge–donor structures. It was found, as in our previous studies (Tillotson et al., 2019[Tillotson, J. P., Bogdanov, G., Jucov, E. V., Khrustalev, V. N., Rigin, S., Hales, J. M., Perry, J. W. & Timofeeva, T. V. (2019). J. Mol. Struct. 1189, 146-154.]), that with an increase of the length of the π-conjugated bridge the mol­ecule becomes less planar, and the angles between the different planar fragments (acceptor–bridge, bridge–donor) become larger (Table 1[link]).

Table 1
Dihedral angles between mol­ecular fragments (°) and mean deviations (Å) of atoms from these fragments

  ID[1] ID[2]
Acceptor–bridge 1.31 (11) 11.6 (2)
Bridge–donor 2.63 (11) 4.9 (3)
     
Deviation in acceptor 0.0325 0.0159
Deviation in bridge 0.0000 0.0473
Deviation in donor 0.0035 0.0073

Compound ID[1] has an almost planar structure, with the benzene ring (C10–C15) being inclined to the mean plane of the indene ring system (C1–C9) by 3.19 (4)°. In ID[2] the deviation from planarity is somewhat larger with the benzene ring (C10–C15) being inclined to the mean plane of the indene ring system (C1–C9) by 13.06 (8)°; see further details in Table 1[link].

3. Supra­molecular features

Mol­ecules of ID[1] and ID[2] have significant dipole moments, which is very common for NLO chromophores. Because of this, mol­ecules have a trend to anti­parallel packing, which is observed in the crystal structures of both ID[1] and ID[2].

In the crystal of ID[1], mol­ecules form two almost perpendicular stacks with anangle of ca 84.47° between them. The mol­ecules, which stack in an anti­parallel or head-to-tail fashion, are linked by C—H⋯O hydrogen bonds (Fig. 2[link], Table 2[link]), forming layers lying parallel to the bc plane. Within the layers there are C—H⋯π inter­actions present (Table 2[link]).

Table 2
Hydrogen-bond geometry (Å, °) for ID[1][link]

Cg2 and Cg3 are the centroids of the C4–C9 and C10–C15 rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C14—H14⋯O1 0.95 2.17 3.0143 (12) 147
C7—H7⋯O3i 0.95 2.58 3.4813 (14) 159
C11—H11⋯O1ii 0.95 2.37 3.2778 (11) 160
C16—H16A⋯Cg3iii 0.98 2.91 3.7948 (12) 151
C17—H17A⋯Cg2iv 0.98 2.83 3.6591 (13) 143
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) -x+1, -y+2, -z+1; (iv) -x+1, -y+1, -z+1.
[Figure 2]
Figure 2
Views along (a) the a axis and (b) the c axis of the crystal packing of ID[1]. The hydrogen bonds (Table 2[link]) are shown as dashed lines. For clarity, only the H atoms involved in the inter­molecular inter­actions have been included.

In the crystal of ID[2], mol­ecules form stacks with parallel mol­ecular positions, and shifted positions of stacks extended along the b-axis direction within the acentric space group P21. The ID[2] mol­ecules are packed in a herringbone fashion (Fig. 3[link]). Here, the angle between two mol­ecules from different stacks is ca 60.8°. The mol­ecules are linked by C—H⋯O hydrogen bonds (Table 3[link]), forming a 21 helix that propagates along the b-axis direction. The mol­ecules in the helix are linked by offset π–π inter­actions with, for example, a centroid–centroid distance Cg1⋯Cg1i of 3.9664 (13) Å [symmetry code: (i) x, y − 1, z] separating the indene ring systems (C1–C9), with an offset of 1.869 Å.

Table 3
Hydrogen-bond geometry (Å, °) for ID[2][link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C19—H19⋯O1 0.95 2.51 3.118 (3) 122
C17—H17C⋯O3i 0.98 2.50 3.463 (3) 169
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+1].
[Figure 3]
Figure 3
Views along (a) the b axis and (b) the c axis of the crystal packing of ID[2]. The hydrogen bonds (Table 3[link]) are shown as dashed lines. For clarity, only the H atoms involved in the inter­molecular inter­actions have been included.

4. Spectroscopic studies

Absorbance spectra were obtained for both ID[1] and ID[2] in chloro­form and aceto­nitrile. For donor–acceptor polyenes, the dominating feature of the absorbance spectrum is the π–π* transition that results from charge transfer from donor to acceptor. According to recent studies (Bogdanov et al., 2019[Bogdanov, G., Tillotson, J. P., Khrustalev, V. N., Rigin, S. & Timofeeva, T. V. (2019). Acta Cryst. C75, 1175-1181.]), it proves that di­methyl­amino­phenyl polyenals have reversed solvatochromism, which is proved by the maxima of the absorption values (Table 4[link]), showing that both ID[1] and ID[2] have their peaks higher in chloro­form than in aceto­nitrile; see the absorption spectra of ID[1] and ID[2] in aceto­nitrile given in Fig. 4[link].

Table 4
Absorption maxima (nm) for ID[1] and ID[2] in chloro­form and aceto­nitrile

Solvent ID[1] ID[2]
Chloro­form 483 539
Aceto­nitrile 480 526
[Figure 4]
Figure 4
Normalized absorbance spectra (nm) in aceto­nitrile for ID[1] and ID[2].

5. Electrochemical measurements

Donor–acceptor polyenes can be characterized by electrochemical measurements to show their ability to transfer electrons. The voltammagrams (Fig. 5[link]) demonstrate a completely reversible oxidation process and a partially reversible reduction process. When only swept between 0 V and 1.7 V the oxidation process is reversible (Fig. 5[link]a), however, when swept to −1.9 V the reduction is only partly reversible (Fig. 5[link]b). This represents the ability of the compound to `easily' transfer electrons through the chain from donor towards acceptor.

[Figure 5]
Figure 5
Cyclic voltammagrams of ID[1]: (a) sweep from 0 to 1.7 V and (b) sweep from −1.9 to 1.7 V.

Note: cyclic voltammagrams of ID[1] were made against FeCp2+/0 (inter­nal reference E1/2+/0 = 0.55 V vs Ag/AgCl) in di­chloro­methane with 0.1 M nBu4NPF6). Measurements were recorded at 50 mV s−1 using a BAS Potentiostat using a glassy carbon working electrode, Pt wire auxilliary electrode and a Ag/AgCl reference electrode.

6. Database survey

A search of the Cambridge Structural Database (CSD Version 5.40, update May 2019; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) for the substructure of ID[1] yielded 27 hits. Three of them, 2-(p-di­ethyl­amino­benzyl­idene)-1,3-indandione (CSD refcode TELWEM; Khodorkovsky et al., 1996[Khodorkovsky, V., Mazor, R. A. & Ellern, A. (1996). Acta Cryst. C52, 2878-2880.]), which has ethyl groups instead of methyl groups in the donor, 2-{[4-(di­phenyl­amino)­phen­yl]methyl­idene}-1H-indene-1,3(2H)-dione (QENYEQ at 223 K: Hariharan et al., 2018[Hariharan, P. S., Gayathri, P., Kundu, A., Karthikeyan, S., Moon, D. & Anthony, S. P. (2018). CrystEngComm, 20, 643-651.]; QENYEQ01 at 150 K: Redon et al., 2018[Redon, S., Eucat, G., Ipuy, M., Jeanneau, E., Gautier-Luneau, I., Ibanez, A., Andraud, C. & Bretonnière, Y. (2018). Dyes Pigments, 156, 116-132.]), which has methyl groups in the donor, and 2-{[4-(di­butyl­amino)­phen­yl]methyl­idene}-1H-indene-1,3(2H)-di­one (BIQYUY; Situ et al., 2019[Situ, B., Gao, M., He, X., Li, S., He, B., Guo, F., Kang, C., Liu, S., Yang, L., Jiang, M., Hu, Y., Tang, B. Z. & Zheng, L. (2019). Mater. Horiz. 6, 546-553.]), which has butyl groups in the donor. In these three compounds, the benzene ring is inclined to the mean plane of the 2,3-di­hydro-1H-indene ring system by 7.6 (2), 1.66 (6)/1.49 (9) and 5.71 (9)°, for TELWEN, QENYEQ/QENYEQ01 and BIQYUY, respectively, compared to 3.19 (4)° in ID[1].

Also, out of all 27 hits there are three hits, (MBYINO: Magomedova et al., 1978[Magomedova, N. S. & Zvonkova, Z. V. (1978). Kristallografiya, 23, 281-288.]; MBYINO01: Magomedova, Neigauz et al., 1980[Magomedova, N. S., Neigauz, M. G., Zvonkova, Z. V. & Novakovskaya, L. A. (1980). Kristallografiya, 25, 400-402.]; MBYINO02: Magomedova & Zvonkova, 1980[Magomedova, N. S. & Zvonkova, Z. V. (1980). Kristallografiya, 25, 1183-1187.]), which are the α, γ and β ID[1] polymorphs, respectively, published over 40 years ago. It should be mentioned that the crystal packing in the α and β polymorphs is centric (space group P21/c), while in the γ polymorph it is acentric (space group Pna21). The crystal structure of ID[1] we obtained corresponds to the β polymorph, i.e. the centrosymmetric modification MBYINO02. The dihedral angles between the benzene and indene rings for two independent mol­ecules in MBYINO are ca 4.35 and 7.79°, compared to ca 7.36° in MBYINO01, and 3.54° in MBYINO02 (cf. 3.19 (4)° in the present crystal structure analysis of ID[1]).

A search of the CSD for the substructure of ID[2] yielded nine hits. Only two structures are similar to that of ID[2]. The first, 2-{3-[4-(di­methyl­amino)­phen­yl]prop-2-yn-1-yl­idene}-1H-indene-1,3(2H)-dione (ZIGPIR; Solanke et al., 2018[Solanke, P., Růžička, A., Mikysek, T., Pytela, O., Bureš, F. & Klikar, M. (2018). Helv. Chim. Acta, 101, e201800090.]), has a triple bond between atoms C18 and C19. The second, 2-[4-(di­methyl­amino)­cinnamo­yl]indan-1,3-dione (CNINDO; Magomedova, Zvonkova et al., 1980[Magomedova, N. S., Zvonkova, Z. V., Geita, L. S., Smelyanskaya, E. M. & Ginzburg, S. L. (1980). Zh. Strukt. Khim. (Russ. J. Struct. Chem.), 21, 131-132.]) has a hydroxyl group attached to atom C18. Like ID[2], it crystallizes in the chiral monoclinic space group P21. The benzene ring is inclined to the mean plane of the indene ring system by ca 11.42° in CNINDO compared to 13.06 (8)° in ID[2]. In ZIGPIR this dihedral angle is smaller at 8.6 (3)°.

7. Synthesis and crystallization

For the synthesis of the title compounds, two aldehydes were used: 4-(di­methyl­amino)­benzaldehyde (A1; purchased from Aldrich) and 4-(di­methyl­amino)­cinnamaldehyde (A2), which was synthesized as described previously (Tillotson, et al., 2019[Tillotson, J. P., Bogdanov, G., Jucov, E. V., Khrustalev, V. N., Rigin, S., Hales, J. M., Perry, J. W. & Timofeeva, T. V. (2019). J. Mol. Struct. 1189, 146-154.]). 2,3-Indanedione was purchased from Aldrich and used without further purification.

Synthesis of 2-[4-(di­methyl­amino)­benzyl­idene]indane-1,3-dione (ID[1]): Aldehyde A1 (2.00 g, 13.4 mmol) and 1,3-indanedione (2.01 g, 13.4 mmol) were suspended in 100 ml of absolute ethanol. The mixture was gently heated until the solids had dissolved. After about 10 min of stirring the dissolution was complete, and a red crystalline precipitate began forming on the walls of the flask. The reaction mixture was stirred vigorously overnight, and the resulting product was collected by filtration then washed with cold ethanol and hexa­nes to give shiny dark-red crystals (yield 3.65 g, 98%; m.p. 477–478 K). ID[1] can be purified by recrystallization using numerous solvent systems (acetone, ethanol, ethyl acetate/hexane, di­chloro­methane/hexane and toluene (to name a few), many of which afforded single crystals. 1H NMR (400 MHz, CD2Cl2) δ 8.52 (d, J = 9.16 Hz, 2H), 7.91–9.73 (m, 4H), 7.71 (s, 1H), 6.77 (d, J = 9.16 HZ, 2H), 3.14 (s, 6H) ppm. 13C NMR (100 MHz, CD2Cl2) δ 191.6, 190.1, 154.5, 147.3, 142.7, 140.3, 138.2, 134.8, 134.5, 123.3, 122.7, 122.6, 122.2, 111.7, 40.3 ppm.

Synthesis of (E)-2-{3-[4-(di­methyl­amino)­phen­yl]allyl­idene}indane-1,3-dione (ID[2]): Aldehyde A2 (1.00 g, 5.71 mmol), 1,3-indanedione (0.85 g, 5.7 mmol) and piperidine (0.15 ml, 1.4 mmol) in ethanol (50 ml) were mixed and treated as for the synthesis of ID[1]. The crude product obtained was collected by filtration and washed with cold ethanol before being recrystallized from ethanol to give incredibly shiny and thin purple actinic crystals (1.55 g, 90%; m.p. 535–537 K). They were washed with hexane and dried under vacuum. 1H NMR (400 MHz, CD2Cl2) δ 8.25 (dd, J = 15.0, 12.2 Hz, 1H), 7.90–7.86 (m, 2H), 7.76–7.73 (m, 2H), 7.60 (d, J = 12.2 Hz, 1H), 7.60 (d, J = 9.0 Hz, 2H), 7.34 (d, J = 15.0 Hz, 1H), 6.72 (d, J = 9.0 Hz, 2H), 3.08 (s, 6H) ppm.

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5[link]. For both structures, the C-bound hydrogen atoms were positioned geometrically and refined using a riding model: C—H = 0.95–0.98 Å with Uiso(H) = 1.5Ueq(C-meth­yl) and 1.2Uiso(C) for other H atoms.

Table 5
Experimental details

  ID[1] ID[2]
Crystal data
Chemical formula C18H15NO2 C20H17NO2
Mr 277.31 303.35
Crystal system, space group Monoclinic, P21/c Monoclinic, P21
Temperature (K) 150 150
a, b, c (Å) 9.2298 (9), 9.0302 (9), 16.7375 (17) 11.072 (2), 3.9664 (8), 17.557 (4)
β (°) 97.863 (1) 104.500 (2)
V (Å3) 1381.9 (2) 746.5 (3)
Z 4 2
Radiation type Mo Kα Mo Kα
μ (mm−1) 0.09 0.09
Crystal size (mm) 0.40 × 0.20 × 0.15 0.40 × 0.12 × 0.10
 
Data collection
Diffractometer Bruker APEXII CCD Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.]) Multi-scan (SADABS; Krause et al., 2015[Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3-10.])
Tmin, Tmax 0.673, 0.746 0.584, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 15794, 4391, 3812 8685, 4531, 4358
Rint 0.041 0.044
(sin θ/λ)max (Å−1) 0.741 0.739
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.139, 1.07 0.044, 0.121, 1.12
No. of reflections 4391 4531
No. of parameters 192 210
No. of restraints 0 1
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.27, −0.40 0.22, −0.33
Absolute structure – Flack x determined using 1732 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter – −0.1 (5)
Computer programs: APEX3 and SAINT (Bruker, 2015[Bruker (2015). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT2017/1 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC references: 1956419; 1956418; 1956418; 1956419

Crystal structure: contains datablocks ID1, ID2, Gobal. DOI: https://doi.org/10.1107/S205698901901329X/su5515sup1.cif

Structure factors: contains datablock ID1. DOI: https://doi.org/10.1107/S205698901901329X/su5515ID1sup2.hkl

Structure factors: contains datablock ID2. DOI: https://doi.org/10.1107/S205698901901329X/su5515ID2sup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698901901329X/su5515ID1sup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S205698901901329X/su5515ID2sup5.cml

checkCIF report


Computing details top

For both structures, data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2017/1 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

2-[4-(Dimethylamino)benzylidene]-1H-indene-1,3(2H)-dione (ID1) top
Crystal data top
C18H15NO2F(000) = 584
Mr = 277.31Dx = 1.333 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.2298 (9) ÅCell parameters from 8518 reflections
b = 9.0302 (9) Åθ = 2.2–31.5°
c = 16.7375 (17) ŵ = 0.09 mm−1
β = 97.863 (1)°T = 150 K
V = 1381.9 (2) Å3Block, purple
Z = 40.40 × 0.20 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer		3812 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
φ and ω scansθmax = 31.8°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)		h = −13→12
Tmin = 0.673, Tmax = 0.746k = −12→12
15794 measured reflectionsl = −23→23
4391 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0835P)2 + 0.2073P]
where P = (Fo2 + 2Fc2)/3
4391 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.27 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O30.93689 (8)0.32542 (8)0.50819 (4)0.03149 (17)
O10.60774 (9)0.60246 (9)0.32291 (4)0.0379 (2)
N100.31173 (9)0.97003 (9)0.60039 (5)0.02873 (18)
C130.60837 (9)0.65851 (10)0.52818 (5)0.02205 (17)
C20.75196 (9)0.49196 (9)0.44122 (5)0.02184 (17)
C180.71343 (9)0.55144 (10)0.51060 (5)0.02284 (17)
H180.7693810.5126030.5578170.027*
C40.89040 (10)0.33908 (10)0.36262 (5)0.02526 (18)
C120.60627 (10)0.69512 (10)0.61024 (5)0.02429 (18)
H120.6734180.6470100.6499790.029*
C30.86960 (9)0.37921 (10)0.44692 (5)0.02369 (18)
C110.51125 (10)0.79732 (10)0.63494 (5)0.02506 (18)
H110.5147280.8192760.6906770.030*
C150.40888 (10)0.83354 (10)0.49501 (5)0.02435 (18)
H150.3410380.8805510.4551850.029*
C140.50520 (10)0.73202 (10)0.47141 (5)0.02373 (18)
H140.5025650.7105980.4156580.028*
C100.40801 (9)0.87012 (9)0.57750 (5)0.02255 (17)
C10.70060 (10)0.51650 (10)0.35504 (5)0.02429 (18)
C50.78862 (10)0.41613 (10)0.30928 (5)0.02495 (18)
C60.78078 (12)0.39789 (12)0.22630 (6)0.0329 (2)
H60.7101430.4496910.1901250.039*
C90.98955 (12)0.24303 (13)0.33465 (7)0.0347 (2)
H91.0593970.1906030.3709990.042*
C70.87982 (14)0.30121 (14)0.19785 (7)0.0392 (3)
H70.8768100.2864480.1414530.047*
C170.31815 (13)1.01545 (13)0.68433 (7)0.0369 (2)
H17A0.2970020.9302050.7170830.055*
H17B0.2456491.0933420.6885450.055*
H17C0.4161091.0533490.7038300.055*
C160.19759 (12)1.03450 (12)0.54226 (7)0.0367 (2)
H16A0.2423181.0892170.5013650.055*
H16B0.1381871.1021980.5700430.055*
H16C0.1353580.9555110.5161970.055*
C80.98325 (14)0.22601 (14)0.25148 (7)0.0409 (3)
H81.0508500.1618330.2309030.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0289 (3)0.0367 (4)0.0275 (3)0.0027 (3)−0.0011 (3)0.0068 (3)
O10.0502 (5)0.0424 (4)0.0201 (3)0.0190 (3)0.0011 (3)0.0033 (3)
N100.0287 (4)0.0296 (4)0.0275 (4)0.0028 (3)0.0026 (3)−0.0008 (3)
C130.0230 (4)0.0253 (4)0.0174 (3)−0.0038 (3)0.0009 (3)0.0006 (3)
C20.0224 (4)0.0237 (4)0.0190 (4)−0.0023 (3)0.0015 (3)0.0023 (3)
C180.0233 (4)0.0263 (4)0.0183 (3)−0.0032 (3)0.0003 (3)0.0023 (3)
C40.0244 (4)0.0261 (4)0.0258 (4)−0.0015 (3)0.0052 (3)0.0014 (3)
C120.0254 (4)0.0291 (4)0.0174 (3)−0.0012 (3)−0.0007 (3)0.0010 (3)
C30.0214 (4)0.0257 (4)0.0236 (4)−0.0035 (3)0.0017 (3)0.0027 (3)
C110.0277 (4)0.0288 (4)0.0178 (3)−0.0024 (3)0.0003 (3)−0.0015 (3)
C150.0246 (4)0.0280 (4)0.0194 (4)−0.0021 (3)−0.0008 (3)0.0034 (3)
C140.0253 (4)0.0281 (4)0.0172 (3)−0.0032 (3)0.0008 (3)0.0012 (3)
C100.0224 (4)0.0221 (4)0.0228 (4)−0.0046 (3)0.0017 (3)0.0006 (3)
C10.0291 (4)0.0251 (4)0.0187 (4)0.0003 (3)0.0031 (3)0.0013 (3)
C50.0277 (4)0.0256 (4)0.0218 (4)−0.0005 (3)0.0047 (3)0.0006 (3)
C60.0401 (5)0.0365 (5)0.0224 (4)0.0059 (4)0.0056 (4)0.0000 (4)
C90.0308 (5)0.0378 (5)0.0363 (5)0.0076 (4)0.0072 (4)0.0026 (4)
C70.0470 (6)0.0444 (6)0.0283 (5)0.0076 (5)0.0126 (4)−0.0028 (4)
C170.0393 (5)0.0389 (5)0.0333 (5)0.0040 (4)0.0079 (4)−0.0076 (4)
C160.0306 (5)0.0324 (5)0.0449 (6)0.0041 (4)−0.0026 (4)0.0035 (4)
C80.0427 (6)0.0441 (6)0.0385 (5)0.0122 (5)0.0145 (5)−0.0021 (5)
Geometric parameters (Å, º) top
O3—C31.2243 (11)C15—C141.3722 (13)
O1—C11.2249 (11)C15—C101.4207 (12)
N10—C101.3578 (12)C15—H150.9500
N10—C161.4543 (13)C14—H140.9500
N10—C171.4570 (13)C1—C51.4961 (13)
C13—C141.4152 (12)C5—C61.3907 (13)
C13—C121.4155 (12)C6—C71.3941 (15)
C13—C181.4281 (12)C6—H60.9500
C2—C181.3700 (12)C9—C81.3939 (16)
C2—C11.4721 (11)C9—H90.9500
C2—C31.4820 (12)C7—C81.3941 (17)
C18—H180.9500C7—H70.9500
C4—C91.3879 (13)C17—H17A0.9800
C4—C51.3907 (13)C17—H17B0.9800
C4—C31.4943 (13)C17—H17C0.9800
C12—C111.3751 (13)C16—H16A0.9800
C12—H120.9500C16—H16B0.9800
C11—C101.4190 (12)C16—H16C0.9800
C11—H110.9500C8—H80.9500
C10—N10—C16121.29 (9)C11—C10—C15117.27 (8)
C10—N10—C17121.15 (8)O1—C1—C2129.63 (8)
C16—N10—C17117.56 (9)O1—C1—C5123.74 (8)
C14—C13—C12116.40 (8)C2—C1—C5106.61 (7)
C14—C13—C18126.35 (8)C6—C5—C4121.34 (9)
C12—C13—C18117.25 (8)C6—C5—C1128.71 (8)
C18—C2—C1133.27 (8)C4—C5—C1109.93 (8)
C18—C2—C3119.19 (8)C5—C6—C7117.92 (9)
C1—C2—C3107.54 (7)C5—C6—H6121.0
C2—C18—C13134.62 (8)C7—C6—H6121.0
C2—C18—H18112.7C4—C9—C8117.80 (10)
C13—C18—H18112.7C4—C9—H9121.1
C9—C4—C5120.99 (9)C8—C9—H9121.1
C9—C4—C3130.22 (9)C6—C7—C8120.56 (10)
C5—C4—C3108.79 (8)C6—C7—H7119.7
C11—C12—C13122.85 (8)C8—C7—H7119.7
C11—C12—H12118.6N10—C17—H17A109.5
C13—C12—H12118.6N10—C17—H17B109.5
O3—C3—C2127.57 (8)H17A—C17—H17B109.5
O3—C3—C4125.36 (9)N10—C17—H17C109.5
C2—C3—C4107.06 (7)H17A—C17—H17C109.5
C12—C11—C10120.27 (8)H17B—C17—H17C109.5
C12—C11—H11119.9N10—C16—H16A109.5
C10—C11—H11119.9N10—C16—H16B109.5
C14—C15—C10121.68 (8)H16A—C16—H16B109.5
C14—C15—H15119.2N10—C16—H16C109.5
C10—C15—H15119.2H16A—C16—H16C109.5
C15—C14—C13121.53 (8)H16B—C16—H16C109.5
C15—C14—H14119.2C9—C8—C7121.37 (10)
C13—C14—H14119.2C9—C8—H8119.3
N10—C10—C11121.43 (8)C7—C8—H8119.3
N10—C10—C15121.31 (8)
C1—C2—C18—C130.93 (17)C12—C11—C10—C15−0.50 (13)
C3—C2—C18—C13−179.71 (9)C14—C15—C10—N10−179.59 (8)
C14—C13—C18—C22.59 (16)C14—C15—C10—C110.04 (13)
C12—C13—C18—C2−177.54 (9)C18—C2—C1—O11.45 (18)
C14—C13—C12—C11−0.66 (13)C3—C2—C1—O1−177.97 (10)
C18—C13—C12—C11179.46 (8)C18—C2—C1—C5179.75 (9)
C18—C2—C3—O32.96 (14)C3—C2—C1—C50.33 (9)
C1—C2—C3—O3−177.53 (9)C9—C4—C5—C61.13 (15)
C18—C2—C3—C4−178.21 (8)C3—C4—C5—C6−178.70 (9)
C1—C2—C3—C41.30 (9)C9—C4—C5—C1−177.34 (9)
C9—C4—C3—O3−3.52 (16)C3—C4—C5—C12.83 (10)
C5—C4—C3—O3176.28 (9)O1—C1—C5—C6−1.89 (16)
C9—C4—C3—C2177.62 (10)C2—C1—C5—C6179.68 (10)
C5—C4—C3—C2−2.58 (10)O1—C1—C5—C4176.43 (9)
C13—C12—C11—C100.83 (14)C2—C1—C5—C4−2.00 (10)
C10—C15—C14—C130.11 (13)C4—C5—C6—C7−0.91 (16)
C12—C13—C14—C150.18 (13)C1—C5—C6—C7177.25 (10)
C18—C13—C14—C15−179.95 (8)C5—C4—C9—C8−0.25 (16)
C16—N10—C10—C11−174.40 (9)C3—C4—C9—C8179.53 (10)
C17—N10—C10—C114.97 (14)C5—C6—C7—C8−0.15 (18)
C16—N10—C10—C155.21 (14)C4—C9—C8—C7−0.81 (18)
C17—N10—C10—C15−175.41 (9)C6—C7—C8—C91.0 (2)
C12—C11—C10—N10179.13 (8)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg3 are the centroids of the C4–C9 and C10–C15 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C14—H14···O10.952.173.0143 (12)147
C7—H7···O3i0.952.583.4813 (14)159
C11—H11···O1ii0.952.373.2778 (11)160
C16—H16A···Cg3iii0.982.913.7948 (12)151
C17—H17A···Cg2iv0.982.833.6591 (13)143
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) −x+1, −y+2, −z+1; (iv) −x+1, −y+1, −z+1.
(E)-2-{3-[4-(Dimethylamino)phenyl]allylidene}-1H-indene-1,3(2H)-dione (ID2) top
Crystal data top
C20H17NO2F(000) = 320
Mr = 303.35Dx = 1.350 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.072 (2) ÅCell parameters from 6074 reflections
b = 3.9664 (8) Åθ = 2.4–31.6°
c = 17.557 (4) ŵ = 0.09 mm−1
β = 104.500 (2)°T = 150 K
V = 746.5 (3) Å3Needle, blue
Z = 20.40 × 0.12 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer		4358 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
φ and ω scansθmax = 31.7°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)		h = −15→16
Tmin = 0.584, Tmax = 0.746k = −5→5
8685 measured reflectionsl = −24→25
4531 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.2055P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
4531 reflectionsΔρmax = 0.22 e Å−3
210 parametersΔρmin = −0.33 e Å−3
1 restraintAbsolute structure: Flack x determined using 1732 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: dualAbsolute structure parameter: −0.1 (5)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O30.50946 (14)0.2510 (5)0.17850 (9)0.0331 (4)
O10.11093 (14)0.5986 (5)0.20367 (9)0.0328 (4)
N100.15603 (16)0.3906 (5)0.69990 (9)0.0253 (4)
C130.29025 (17)0.2553 (5)0.49784 (10)0.0203 (3)
C100.20054 (16)0.3470 (5)0.63500 (10)0.0202 (3)
C120.35740 (17)0.1388 (5)0.57237 (11)0.0232 (4)
H120.4343330.0252050.5765570.028*
C90.37083 (18)0.5984 (6)0.02319 (11)0.0250 (4)
H90.4503100.5284510.0177450.030*
C110.31564 (18)0.1834 (5)0.63920 (11)0.0236 (4)
H110.3642930.1039460.6883970.028*
C70.16966 (19)0.8643 (6)−0.03035 (11)0.0276 (4)
H70.1133860.972479−0.0731530.033*
C140.17745 (18)0.4244 (5)0.49465 (11)0.0224 (4)
H140.1306880.5107830.4456470.027*
C190.29104 (17)0.3097 (5)0.35537 (11)0.0230 (4)
H190.2114330.4149400.3421260.028*
C180.35755 (17)0.2675 (5)0.29653 (10)0.0222 (3)
H180.4335770.1449550.3111300.027*
C200.33964 (17)0.2017 (5)0.43054 (11)0.0222 (4)
H200.4149710.0761840.4394460.027*
C170.2246 (2)0.2557 (6)0.77578 (11)0.0294 (4)
H17A0.2369510.0127150.7709330.044*
H17B0.1769650.2960730.8150260.044*
H17C0.3058560.3676090.7923160.044*
C80.2871 (2)0.7601 (6)−0.03803 (11)0.0273 (4)
H80.3096690.800923−0.0859630.033*
C60.13502 (17)0.8102 (5)0.03978 (11)0.0247 (4)
H60.0561400.8826290.0457700.030*
C160.03720 (19)0.5566 (6)0.69463 (13)0.0283 (4)
H16A0.0405500.7874280.6753610.043*
H16B0.0202340.5623740.7467830.043*
H16C−0.0293160.4319040.6581840.043*
C40.33549 (16)0.5416 (5)0.09239 (10)0.0200 (3)
C150.13295 (17)0.4683 (5)0.56017 (11)0.0224 (4)
H150.0558200.5814230.5555470.027*
C30.40481 (17)0.3712 (5)0.16627 (10)0.0216 (3)
C50.21913 (16)0.6474 (5)0.10052 (10)0.0195 (3)
C20.32319 (17)0.3854 (5)0.22113 (10)0.0212 (3)
C10.20501 (17)0.5508 (5)0.18022 (11)0.0219 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0219 (6)0.0463 (10)0.0311 (7)0.0089 (7)0.0068 (5)0.0039 (7)
O10.0235 (6)0.0485 (10)0.0297 (7)0.0070 (7)0.0128 (5)0.0051 (7)
N100.0264 (8)0.0304 (9)0.0201 (7)0.0016 (7)0.0078 (6)0.0028 (7)
C130.0197 (7)0.0221 (8)0.0182 (7)−0.0011 (7)0.0029 (6)0.0026 (6)
C100.0196 (7)0.0211 (8)0.0190 (7)−0.0023 (7)0.0035 (6)0.0013 (6)
C120.0187 (7)0.0278 (9)0.0219 (8)0.0035 (7)0.0028 (6)0.0038 (7)
C90.0241 (8)0.0292 (10)0.0240 (8)−0.0017 (8)0.0103 (7)−0.0015 (7)
C110.0214 (8)0.0286 (10)0.0189 (7)0.0020 (7)0.0011 (6)0.0041 (7)
C70.0290 (9)0.0305 (10)0.0208 (8)−0.0019 (8)0.0017 (7)0.0038 (8)
C140.0203 (8)0.0245 (9)0.0198 (7)−0.0002 (7)0.0003 (6)0.0041 (7)
C190.0212 (8)0.0267 (9)0.0206 (7)−0.0009 (7)0.0046 (6)0.0010 (7)
C180.0217 (8)0.0237 (9)0.0206 (7)−0.0007 (7)0.0038 (6)−0.0001 (7)
C200.0208 (8)0.0242 (9)0.0213 (8)−0.0009 (7)0.0046 (6)0.0008 (7)
C170.0351 (10)0.0348 (11)0.0176 (8)−0.0032 (9)0.0051 (7)0.0012 (8)
C80.0315 (9)0.0313 (10)0.0198 (8)−0.0033 (8)0.0076 (7)0.0005 (7)
C60.0198 (8)0.0288 (10)0.0243 (8)−0.0002 (7)0.0035 (6)0.0026 (7)
C160.0257 (9)0.0299 (10)0.0320 (10)−0.0005 (8)0.0121 (7)−0.0022 (8)
C40.0186 (7)0.0222 (8)0.0191 (7)−0.0014 (7)0.0047 (6)−0.0026 (7)
C150.0185 (8)0.0261 (9)0.0206 (8)0.0021 (7)0.0012 (6)0.0032 (7)
C30.0187 (7)0.0255 (9)0.0206 (7)0.0003 (7)0.0045 (6)−0.0011 (7)
C50.0173 (7)0.0221 (8)0.0186 (7)−0.0013 (6)0.0037 (6)−0.0010 (6)
C20.0189 (7)0.0254 (9)0.0190 (7)0.0001 (7)0.0042 (6)−0.0007 (7)
C10.0195 (7)0.0266 (9)0.0201 (7)−0.0001 (7)0.0059 (6)0.0002 (7)
Geometric parameters (Å, º) top
O3—C31.221 (2)C19—C201.364 (3)
O1—C11.227 (2)C19—C181.421 (2)
N10—C101.361 (2)C19—H190.9500
N10—C161.453 (3)C18—C21.365 (3)
N10—C171.460 (3)C18—H180.9500
C13—C141.406 (3)C20—H200.9500
C13—C121.411 (2)C17—H17A0.9800
C13—C201.437 (2)C17—H17B0.9800
C10—C111.416 (3)C17—H17C0.9800
C10—C151.423 (2)C8—H80.9500
C12—C111.376 (3)C6—C51.387 (3)
C12—H120.9500C6—H60.9500
C9—C41.385 (2)C16—H16A0.9800
C9—C81.389 (3)C16—H16B0.9800
C9—H90.9500C16—H16C0.9800
C11—H110.9500C4—C51.396 (2)
C7—C61.395 (3)C4—C31.493 (3)
C7—C81.402 (3)C15—H150.9500
C7—H70.9500C3—C21.478 (2)
C14—C151.371 (3)C5—C11.496 (2)
C14—H140.9500C2—C11.479 (3)
C10—N10—C16121.07 (16)H17A—C17—H17B109.5
C10—N10—C17120.19 (17)N10—C17—H17C109.5
C16—N10—C17118.67 (16)H17A—C17—H17C109.5
C14—C13—C12116.72 (16)H17B—C17—H17C109.5
C14—C13—C20123.71 (16)C9—C8—C7121.16 (18)
C12—C13—C20119.57 (17)C9—C8—H8119.4
N10—C10—C11121.65 (16)C7—C8—H8119.4
N10—C10—C15120.86 (17)C5—C6—C7118.06 (18)
C11—C10—C15117.49 (16)C5—C6—H6121.0
C11—C12—C13122.48 (17)C7—C6—H6121.0
C11—C12—H12118.8N10—C16—H16A109.5
C13—C12—H12118.8N10—C16—H16B109.5
C4—C9—C8118.26 (18)H16A—C16—H16B109.5
C4—C9—H9120.9N10—C16—H16C109.5
C8—C9—H9120.9H16A—C16—H16C109.5
C12—C11—C10120.33 (16)H16B—C16—H16C109.5
C12—C11—H11119.8C9—C4—C5120.77 (17)
C10—C11—H11119.8C9—C4—C3129.72 (17)
C6—C7—C8120.39 (18)C5—C4—C3109.52 (15)
C6—C7—H7119.8C14—C15—C10121.01 (17)
C8—C7—H7119.8C14—C15—H15119.5
C15—C14—C13121.95 (17)C10—C15—H15119.5
C15—C14—H14119.0O3—C3—C2127.48 (18)
C13—C14—H14119.0O3—C3—C4126.02 (17)
C20—C19—C18121.06 (18)C2—C3—C4106.49 (15)
C20—C19—H19119.5C6—C5—C4121.36 (16)
C18—C19—H19119.5C6—C5—C1129.12 (16)
C2—C18—C19126.54 (18)C4—C5—C1109.51 (15)
C2—C18—H18116.7C18—C2—C3123.48 (17)
C19—C18—H18116.7C18—C2—C1128.36 (17)
C19—C20—C13127.60 (18)C3—C2—C1108.14 (15)
C19—C20—H20116.2O1—C1—C2128.88 (18)
C13—C20—H20116.2O1—C1—C5124.79 (17)
N10—C17—H17A109.5C2—C1—C5106.31 (15)
N10—C17—H17B109.5
C16—N10—C10—C11−179.48 (19)C5—C4—C3—O3−179.7 (2)
C17—N10—C10—C11−2.5 (3)C9—C4—C3—C2179.4 (2)
C16—N10—C10—C151.1 (3)C5—C4—C3—C2−1.0 (2)
C17—N10—C10—C15178.13 (19)C7—C6—C5—C40.3 (3)
C14—C13—C12—C110.5 (3)C7—C6—C5—C1−178.4 (2)
C20—C13—C12—C11179.7 (2)C9—C4—C5—C60.4 (3)
C13—C12—C11—C100.9 (3)C3—C4—C5—C6−179.24 (18)
N10—C10—C11—C12179.1 (2)C9—C4—C5—C1179.36 (18)
C15—C10—C11—C12−1.5 (3)C3—C4—C5—C1−0.3 (2)
C12—C13—C14—C15−1.4 (3)C19—C18—C2—C3171.6 (2)
C20—C13—C14—C15179.5 (2)C19—C18—C2—C1−6.9 (4)
C20—C19—C18—C2−175.0 (2)O3—C3—C2—C181.7 (3)
C18—C19—C20—C13173.3 (2)C4—C3—C2—C18−176.93 (19)
C14—C13—C20—C192.4 (3)O3—C3—C2—C1−179.5 (2)
C12—C13—C20—C19−176.7 (2)C4—C3—C2—C11.9 (2)
C4—C9—C8—C70.1 (3)C18—C2—C1—O1−4.8 (4)
C6—C7—C8—C90.7 (3)C3—C2—C1—O1176.5 (2)
C8—C7—C6—C5−0.9 (3)C18—C2—C1—C5176.7 (2)
C8—C9—C4—C5−0.6 (3)C3—C2—C1—C5−2.0 (2)
C8—C9—C4—C3179.0 (2)C6—C5—C1—O11.7 (3)
C13—C14—C15—C100.8 (3)C4—C5—C1—O1−177.2 (2)
N10—C10—C15—C14−179.92 (19)C6—C5—C1—C2−179.7 (2)
C11—C10—C15—C140.7 (3)C4—C5—C1—C21.4 (2)
C9—C4—C3—O30.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19···O10.952.513.118 (3)122
C17—H17C···O3i0.982.503.463 (3)169
Symmetry code: (i) −x+1, y+1/2, −z+1.
Dihedral angles between molecular fragments (°) and mean deviations (Å) of atoms from these fragments top
ID[1]ID[2]
Acceptor–bridge1.31 (11)11.6 (2)
Bridge–donor2.63 (11)4.9 (3)
Deviation in acceptor0.03250.0159
Deviation in bridge0.00000.0473
Deviation in donor0.00350.0073
Absorption maxima (nm) for ID[1] and ID[2] in chloroform and acetonitrile top
SolventID[1]ID[2]
Chloroform483539
Acetonitrile480526
 

Funding information

Funding for this research was provided by: National Science Foundation (grant Nos. DMR-0934212 and DMR-1523611); Foundation for the National Institutes of Health (grant No. 1R21NS084353-01).

References

First citationAndreu, R., Garín, J., Orduna, J., Alcalá, R. & Villacampa, B. (2003). Org. Lett. 5, 3143–3146.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationBogdanov, G., Tillotson, J. P., Khrustalev, V. N., Rigin, S. & Timofeeva, T. V. (2019). Acta Cryst. C75, 1175–1181.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationBruker (2015). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDuarte, A., Pu, K.-Y., Liu, B. & Bazan, G. C. (2011). Chem. Mater. 23, 501–515.  Web of Science CrossRef CAS Google Scholar
 First citationGroom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationHariharan, P. S., Gayathri, P., Kundu, A., Karthikeyan, S., Moon, D. & Anthony, S. P. (2018). CrystEngComm, 20, 643–651.  Web of Science CSD CrossRef CAS Google Scholar
 First citationKhodorkovsky, V., Mazor, R. A. & Ellern, A. (1996). Acta Cryst. C52, 2878–2880.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationKrause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10.  Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationMagomedova, N. S., Neigauz, M. G., Zvonkova, Z. V. & Novakovskaya, L. A. (1980). Kristallografiya, 25, 400–402.  CAS Google Scholar
 First citationMagomedova, N. S. & Zvonkova, Z. V. (1978). Kristallografiya, 23, 281–288.  CAS Google Scholar
 First citationMagomedova, N. S. & Zvonkova, Z. V. (1980). Kristallografiya, 25, 1183–1187.  CAS Google Scholar
 First citationMagomedova, N. S., Zvonkova, Z. V., Geita, L. S., Smelyanskaya, E. M. & Ginzburg, S. L. (1980). Zh. Strukt. Khim. (Russ. J. Struct. Chem.), 21, 131–132.  CAS Google Scholar
 First citationMüller, C. D., Falcou, A., Reckefuss, N., Rojahn, M., Wiederhirn, V., Rudati, P., Frohne, H., Nuyken, O., Becker, H. & Meerholz, K. (2003). Nature, 421, 829–833.  Web of Science PubMed Google Scholar
 First citationOliveira, A. F. C. D. S., de Souza, A. P. M., de Oliveira, A. S., da Silva, M. L., de Oliveira, F. M., Santos, E. G., da Silva, Í. E. P., Ferreira, R. S., Villela, F. S., Martins, F. T., Leal, D. H. S., Vaz, B. G., Teixeira, R. R. & de Paula, S. O. (2018). Eur. J. Med. Chem. 149, 98–109.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationOrtiz, R., Marder, S. R., Cheng, L.-T., Tiemann, B. G., Cavagnero, S. & Ziller, J. W. (1994). J. Chem. Soc. Chem. Commun. pp. 2263–2264.  CSD CrossRef Web of Science Google Scholar
 First citationParsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationQin, W., Lam, J. W., Yang, Z., Chen, S., Liang, G., Zhao, W., Kwok, H. S. & Tang, B. Z. (2015). Chem. Commun. 51, 7321–7324.  Web of Science CrossRef CAS Google Scholar
 First citationRaimundo, J.-M., Blanchard, P., Gallego-Planas, N., Mercier, N., Ledoux-Rak, I., Hierle, R. & Roncali, J. (2002). J. Org. Chem. 67, 205–218.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationRedon, S., Eucat, G., Ipuy, M., Jeanneau, E., Gautier-Luneau, I., Ibanez, A., Andraud, C. & Bretonnière, Y. (2018). Dyes Pigments, 156, 116–132.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSamuel, I. D. & Turnbull, G. A. (2007). Chem. Rev. 107, 1272–1295.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSitu, B., Gao, M., He, X., Li, S., He, B., Guo, F., Kang, C., Liu, S., Yang, L., Jiang, M., Hu, Y., Tang, B. Z. & Zheng, L. (2019). Mater. Horiz. 6, 546–553.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSolanke, P., Růžička, A., Mikysek, T., Pytela, O., Bureš, F. & Klikar, M. (2018). Helv. Chim. Acta, 101, e201800090.  Web of Science CSD CrossRef Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSuponitsky, K. Y., Timofeeva, T. V. & Antipin, M. Y. (2006). Russ. Chem. Rev. 75, 457–496.  CrossRef CAS Google Scholar
 First citationTillotson, J. P., Bogdanov, G., Jucov, E. V., Khrustalev, V. N., Rigin, S., Hales, J. M., Perry, J. W. & Timofeeva, T. V. (2019). J. Mol. Struct. 1189, 146–154.  Web of Science CSD CrossRef CAS Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 75| Part 11| November 2019| Pages 1595-1599
https://doi.org/10.1107/S205698901901329X
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