In the crystal structure of the title compound intermolecular hydrogen-bonding interactions and weak C—H⋯π interactions between the constituents lead to the formation of a three-dimensional network. Hirshfeld surface analysis revealed that H⋯H interactions dominate the crystal packing.
Keywords: crystal structure, 4-aminobenzoic acid (PABA), anthracene, intermolecular hydrogen bonding, C—H⋯π interactions, Hirshfeld surface analysis
Abstract
The title compound, C22H17NO2·C3H7NO, was synthesized by condensation of an aromatic aldehyde with a secondary amine and subsequent reduction. It was crystallized from a dimethylformamide solution as a monosolvate, C22H17NO2·C3H7NO. The aromatic molecule is non-planar with a dihedral angle between the mean planes of the aniline moiety and the methyl anthracene moiety of 81.36 (8)°. The torsion angle of the Caryl—CH2—NH—Caryl backbone is 175.9 (2)°. The crystal structure exhibits a three-dimensional supramolecular network, resulting from hydrogen-bonding interactions between the carboxylic OH group and the solvent O atom as well as between the amine functionality and the O atom of the carboxylic group and additional C—H⋯π interactions. Hirshfeld surface analysis was performed to quantify the intermolecular interactions.
Chemical context
Schiff bases belong to a class of organic compounds that are formed by the condensation reaction of a carbonyl carbon with an aliphatic/aromatic amine, resulting in the formation of a characteristic imine bond (–HC=N–). Many Schiff bases exhibit activities of biological and pharmaceutical significance. Moreover, Schiff bases are actively used as organic linkers for building metal complexes with interesting properties.
Here we report the synthesis and crystal structure of a reduced Schiff base that was formed by a condensation reaction of anthraldehyde with 4-amino benzoic acid (PABA). The title compound crystallizes with a dimethylformamide (DMF) solvent molecule in a 1:1: ratio. Both anthraldehyde and PABA have shown anticancer (Pavitha et al., 2017 ▸), fluorescence (Obali & Ucan, 2012 ▸; Singh et al., 2014 ▸), sensing (Zhou et al., 2012 ▸ ), antimicrobial (Vidya, 2016 ▸) and magnetic properties (Dianu et al., 2010 ▸).
Structural commentary
The title molecule is non-planar, with the tricyclic fragment nearly perpendicular to the phenyl ring of the PABA moiety, making a dihedral angle of 81.36 (8)° (Fig. 1 ▸). The torsion angle of the Caryl—CH2—NH—Caryl backbone (C9—C8—N1—C5) is 175.9 (2)°. The C8—N1 bond length of 1.452 (3) Å is in agreement with the corresponding bond length of 1.457 (3) Å in the solvent-free compound [CSD (Groom et al., 2016 ▸) refcode RUCJIL; Ahmed et al., 2020 ▸], just as the bond lengths in the carboxylic group of the title compound, C1—O2 = 1.230 (3), C1—O1 = 1.322 (3) Å, are virtually identical with those of the solvent-free compound [1.238 (3) and 1.325 (3) Å, respectively].
Figure 1.
The molecular structures of the components in the title compound. Displacement ellipsoids are drawn at the 50% probability level.
Supramolecular features
Classical hydrogen-bonding interactions between the carboxylic OH group (O1) and the solvent O atom (O3) as well as between the amine functionality (N1) and the O atom of the carboxylic group (O2) lead to the formation of supramolecular layers extending parallel to (10
) (Fig. 2 ▸, Table 1 ▸). C—H⋯π interactions involving the phenyl C—H groups of PABA as donor groups and the π system of the anthracene moiety link adjacent layers into a three-dimensional network (Fig. 3 ▸, Table 1 ▸).
Figure 2.
View along [010] showing a layer formed by hydrogen-bonding interactions between the molecule and the solvent. Purple and blue dashed lines represent the N—H⋯O and O—H⋯O bonds, respectively.
Table 1. Hydrogen-bond geometry (Å, °).
Cg5 and Cg7 are the centroids of the 10-membered ring system C9–C22 and of the 14-membered anthracene moiety, respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O1—H1⋯O3 | 1.02 (4) | 1.59 (4) | 2.590 (3) | 167 (4) |
| N1—H1A⋯O2i | 0.88 (1) | 2.13 (1) | 2.973 (3) | 160 (1) |
| C18—H18⋯O3ii | 0.95 (1) | 2.40 (1) | 3.277 (4) | 154 (1) |
| C6—H6⋯Cg7iii | 0.95 | 2.80 (1) | 3.552 (2) | 137 (1) |
| C7—H7⋯Cg5iii | 0.95 | 2.99 (1) | 3.646 (3) | 138 (1) |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
Figure 3.
The crystal packing showing C—H⋯π interactions between the layers, building up a three-dimensional network.
Hirshfeld Surface Analysis
Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ▸) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ▸) were performed with CrystalExplorer (Turner et al., 2017 ▸). The Hirshfeld surfaces are colour-mapped with the normalized contact distance, d norm, varying from red (distances shorter than the sum of the van der Waals radii) through white to blue (distances longer than the sum of the van der Waals radii). The positions of the O—H⋯O and N—H⋯O hydrogen bonds between the molecules are indicated by the red regions on the Hirshfeld surface (Fig. 4 ▸).
Figure 4.
Hirshfeld surface of the two molecules in the title compound mapped over d norm, in the colour range −0. 461 to 1.471 a.u..
The two-dimensional fingerprint plot (Fig. 5 ▸ a) and those delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) N⋯H/H⋯N and (e) O⋯H/H⋯O interactions reveal contributions of 47.9%, 34.2%, 0.6% and 13.7%, respectively, to the overall surface.
Figure 5.
(a) Two-dimensional fingerprint plot of the title compound, and those delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) N⋯H/H⋯N and (e) O⋯H/H⋯O interactions.
Database survey
Next to the solvent-free crystal structure (RUCJIL; Ahmed et al., 2020 ▸), a search of the Cambridge Structural Database (CSD,Version 5.40, update August 2019; Groom et al., 2016 ▸) for the N-(anthracen-9-ylmethyl)aniline skeleton gave six hits, five polymeric metal complexes of the ligand 5-[(anthracen-9-ylmethyl)amino]isophthalic acid containing gadolinium (VOLSOG, VOLSUM, VOLTAT, VOLTIB; Singh et al., 2014 ▸) and cadmium (EYUMOC; Yan et al., 2016 ▸) as well as an organic molecule with a calix(4)arene ring (Bu et al., 2004 ▸). In these structures, the bridging C—N bond length varies from ≃ 1.389 to 1.494 Å, compared to the C8—N1 bond length of 1.452 (3) Å in the title structure.
Synthesis and crystallization
The Schiff base was synthesized and subsequently reduced by a reported procedure (Ahmed et al., 2020 ▸). To this reduced ligand (0.15 mmol), ethanol and dimethylformamide were added in an equal volume ratio, and the mixture was heated under reflux for 3–4 h at 353 K. The solution was then allowed to cool to room temperature, filtered and kept for slow evaporation. After 10 to 12 d, small colourless block-like crystals began to grow that were dried and characterized by single crystal X-ray diffraction.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. Hydrogen atoms bound to N or O atoms were located in a difference-Fourier map and were freely refined, while the C-bound hydrogen atoms were included in calculated positions and allowed to ride on their parent C atom: C—H = 0.93–0.97 Å with U iso(H) = 1.2U eq(C).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C22H17NO2·C3H7NO |
| M r | 400.48 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 100 |
| a, b, c (Å) | 10.6878 (9), 8.9088 (7), 21.9503 (19) |
| β (°) | 99.049 (3) |
| V (Å3) | 2064.0 (3) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.09 |
| Crystal size (mm) | 0.36 × 0.28 × 0.16 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2016 ▸) |
| T min, T max | 0.368, 0.746 |
| No. of measured, independent and observed [I ≥ 2u(I)] reflections | 31593, 3668, 2477 |
| R int | 0.139 |
| (sin θ/λ)max (Å−1) | 0.596 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.057, 0.184, 1.12 |
| No. of reflections | 3668 |
| No. of parameters | 278 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.47, −0.37 |
Supplementary Material
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989020005393/wm5548sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989020005393/wm5548Isup2.hkl
CCDC reference: 1982147
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors are grateful to the Department of Applied Chemistry, ZHCET, Aligarh Muslim University, Aligarh, U.P., India, for providing laboratory facilities.
supplementary crystallographic information
Crystal data
| C22H17NO2·C3H7NO | F(000) = 848.4030 |
| Mr = 400.48 | Dx = 1.289 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.6878 (9) Å | Cell parameters from 4326 reflections |
| b = 8.9088 (7) Å | θ = 3.2–28.1° |
| c = 21.9503 (19) Å | µ = 0.09 mm−1 |
| β = 99.049 (3)° | T = 100 K |
| V = 2064.0 (3) Å3 | Block, colourless |
| Z = 4 | 0.36 × 0.28 × 0.16 mm |
Data collection
| Bruker APEXII CCD diffractometer | 2477 reflections with I≥ 2u(I) |
| φ and ω scans | Rint = 0.139 |
| Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 25.1°, θmin = 3.0° |
| Tmin = 0.368, Tmax = 0.746 | h = −14→14 |
| 31593 measured reflections | k = −11→11 |
| 3668 independent reflections | l = −29→29 |
Refinement
| Refinement on F2 | 41 constraints |
| Least-squares matrix: full | Primary atom site location: iterative |
| R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.184 | w = 1/[σ2(Fo2) + (0.0846P)2 + 0.3653P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.12 | (Δ/σ)max < 0.001 |
| 3668 reflections | Δρmax = 0.47 e Å−3 |
| 278 parameters | Δρmin = −0.37 e Å−3 |
| 0 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.73134 (18) | 0.7445 (2) | 0.43603 (9) | 0.0355 (5) | |
| O2 | 0.88916 (17) | 0.7377 (2) | 0.38033 (9) | 0.0323 (5) | |
| O3 | 0.83886 (19) | 0.9615 (2) | 0.50335 (9) | 0.0400 (5) | |
| N1 | 0.49557 (19) | 0.2754 (2) | 0.23347 (11) | 0.0271 (5) | |
| H1a | 0.52980 (19) | 0.2410 (2) | 0.20230 (11) | 0.0326 (7)* | |
| N2 | 0.8603 (2) | 1.1906 (2) | 0.46049 (11) | 0.0319 (6) | |
| C1 | 0.7855 (2) | 0.6922 (3) | 0.39023 (13) | 0.0271 (6) | |
| C2 | 0.7105 (2) | 0.5787 (3) | 0.35193 (12) | 0.0239 (6) | |
| C3 | 0.7566 (2) | 0.5171 (3) | 0.30121 (12) | 0.0262 (6) | |
| H3 | 0.8380 (2) | 0.5456 (3) | 0.29315 (12) | 0.0314 (7)* | |
| C4 | 0.6864 (2) | 0.4164 (3) | 0.26299 (13) | 0.0270 (6) | |
| H4 | 0.7197 (2) | 0.3763 (3) | 0.22878 (13) | 0.0324 (8)* | |
| C5 | 0.5653 (2) | 0.3715 (3) | 0.27377 (12) | 0.0242 (6) | |
| C6 | 0.5206 (2) | 0.4299 (3) | 0.32576 (12) | 0.0263 (6) | |
| H6 | 0.4407 (2) | 0.3988 (3) | 0.33498 (12) | 0.0316 (7)* | |
| C7 | 0.5920 (2) | 0.5320 (3) | 0.36341 (12) | 0.0251 (6) | |
| H7 | 0.5597 (2) | 0.5715 (3) | 0.39801 (12) | 0.0302 (7)* | |
| C8 | 0.3682 (2) | 0.2265 (3) | 0.23901 (13) | 0.0272 (6) | |
| H8a | 0.3697 (2) | 0.1682 (3) | 0.27751 (13) | 0.0327 (8)* | |
| H8b | 0.3128 (2) | 0.3149 (3) | 0.24074 (13) | 0.0327 (8)* | |
| C9 | 0.3172 (2) | 0.1300 (3) | 0.18389 (12) | 0.0234 (6) | |
| C10 | 0.2375 (2) | 0.1918 (3) | 0.13285 (12) | 0.0248 (6) | |
| C11 | 0.1944 (3) | 0.3436 (3) | 0.13080 (14) | 0.0344 (7) | |
| H11 | 0.2224 (3) | 0.4081 (3) | 0.16466 (14) | 0.0412 (9)* | |
| C12 | 0.1145 (3) | 0.3979 (4) | 0.08172 (16) | 0.0452 (8) | |
| H12 | 0.0856 (3) | 0.4987 (4) | 0.08225 (16) | 0.0543 (10)* | |
| C13 | 0.0737 (3) | 0.3074 (4) | 0.03015 (16) | 0.0456 (9) | |
| H13 | 0.0174 (3) | 0.3471 (4) | −0.00384 (16) | 0.0548 (10)* | |
| C14 | 0.1141 (3) | 0.1640 (4) | 0.02867 (14) | 0.0372 (7) | |
| H14 | 0.0880 (3) | 0.1048 (4) | −0.00706 (14) | 0.0447 (9)* | |
| C15 | 0.1955 (2) | 0.0998 (3) | 0.07979 (12) | 0.0282 (6) | |
| C16 | 0.2339 (2) | −0.0494 (3) | 0.07998 (13) | 0.0289 (7) | |
| H16 | 0.2064 (2) | −0.1097 (3) | 0.04472 (13) | 0.0347 (8)* | |
| C17 | 0.3112 (2) | −0.1129 (3) | 0.13030 (12) | 0.0266 (6) | |
| C18 | 0.3469 (3) | −0.2670 (3) | 0.13064 (15) | 0.0350 (7) | |
| H18 | 0.3170 (3) | −0.3283 (3) | 0.09599 (15) | 0.0420 (9)* | |
| C19 | 0.4230 (3) | −0.3272 (3) | 0.17973 (16) | 0.0407 (8) | |
| H19 | 0.4447 (3) | −0.4306 (3) | 0.17957 (16) | 0.0489 (10)* | |
| C20 | 0.4701 (3) | −0.2375 (3) | 0.23099 (15) | 0.0368 (7) | |
| H20 | 0.5252 (3) | −0.2804 (3) | 0.26469 (15) | 0.0441 (9)* | |
| C21 | 0.4378 (2) | −0.0896 (3) | 0.23285 (13) | 0.0306 (7) | |
| H21 | 0.4707 (2) | −0.0312 (3) | 0.26793 (13) | 0.0367 (8)* | |
| C22 | 0.3555 (2) | −0.0209 (3) | 0.18322 (12) | 0.0235 (6) | |
| C23 | 0.8782 (3) | 1.0922 (3) | 0.50634 (14) | 0.0318 (7) | |
| H23 | 0.9249 (3) | 1.1247 (3) | 0.54448 (14) | 0.0381 (8)* | |
| C24 | 0.9129 (3) | 1.3401 (3) | 0.46883 (15) | 0.0401 (8) | |
| H24a | 0.8440 (3) | 1.4139 (3) | 0.4638 (9) | 0.0602 (12)* | |
| H24b | 0.9620 (16) | 1.3491 (7) | 0.5103 (3) | 0.0602 (12)* | |
| H24c | 0.9684 (15) | 1.3586 (9) | 0.4381 (6) | 0.0602 (12)* | |
| C25 | 0.7882 (3) | 1.1510 (4) | 0.40096 (14) | 0.0445 (8) | |
| H25a | 0.8462 (3) | 1.136 (2) | 0.3711 (3) | 0.0668 (12)* | |
| H25b | 0.7411 (15) | 1.0580 (13) | 0.4049 (2) | 0.0668 (12)* | |
| H25c | 0.7286 (14) | 1.2320 (11) | 0.3868 (5) | 0.0668 (12)* | |
| H1 | 0.776 (4) | 0.836 (4) | 0.4571 (18) | 0.085 (13)* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0360 (12) | 0.0387 (12) | 0.0343 (12) | −0.0078 (9) | 0.0132 (9) | −0.0087 (10) |
| O2 | 0.0293 (11) | 0.0377 (11) | 0.0307 (11) | −0.0076 (8) | 0.0071 (9) | −0.0032 (9) |
| O3 | 0.0511 (13) | 0.0329 (12) | 0.0356 (13) | −0.0006 (9) | 0.0058 (10) | −0.0041 (10) |
| N1 | 0.0206 (11) | 0.0305 (12) | 0.0311 (13) | −0.0044 (9) | 0.0066 (10) | −0.0092 (10) |
| N2 | 0.0321 (13) | 0.0264 (12) | 0.0366 (15) | 0.0015 (10) | 0.0039 (11) | −0.0002 (11) |
| C1 | 0.0242 (15) | 0.0293 (15) | 0.0288 (16) | 0.0008 (11) | 0.0071 (12) | 0.0040 (12) |
| C2 | 0.0220 (13) | 0.0238 (13) | 0.0260 (15) | 0.0027 (10) | 0.0043 (11) | 0.0031 (11) |
| C3 | 0.0201 (13) | 0.0254 (14) | 0.0331 (16) | −0.0019 (10) | 0.0045 (11) | 0.0012 (12) |
| C4 | 0.0240 (14) | 0.0272 (14) | 0.0311 (16) | 0.0007 (11) | 0.0088 (11) | −0.0040 (12) |
| C5 | 0.0215 (13) | 0.0230 (13) | 0.0278 (15) | 0.0016 (10) | 0.0030 (11) | 0.0018 (12) |
| C6 | 0.0199 (13) | 0.0284 (14) | 0.0316 (16) | 0.0005 (11) | 0.0070 (11) | 0.0012 (12) |
| C7 | 0.0230 (14) | 0.0275 (14) | 0.0255 (15) | 0.0017 (11) | 0.0055 (11) | −0.0011 (12) |
| C8 | 0.0197 (14) | 0.0317 (15) | 0.0309 (16) | −0.0039 (11) | 0.0060 (11) | −0.0039 (12) |
| C9 | 0.0166 (13) | 0.0278 (14) | 0.0267 (15) | −0.0037 (10) | 0.0064 (11) | −0.0007 (12) |
| C10 | 0.0179 (13) | 0.0265 (14) | 0.0311 (16) | −0.0033 (10) | 0.0075 (11) | 0.0036 (12) |
| C11 | 0.0327 (16) | 0.0330 (16) | 0.0387 (18) | 0.0027 (12) | 0.0097 (13) | 0.0042 (14) |
| C12 | 0.0374 (18) | 0.0412 (18) | 0.057 (2) | 0.0063 (14) | 0.0066 (16) | 0.0160 (17) |
| C13 | 0.0301 (17) | 0.058 (2) | 0.047 (2) | 0.0023 (15) | −0.0001 (15) | 0.0250 (17) |
| C14 | 0.0266 (15) | 0.0536 (19) | 0.0307 (17) | −0.0107 (14) | 0.0021 (13) | 0.0099 (15) |
| C15 | 0.0212 (14) | 0.0355 (15) | 0.0284 (16) | −0.0060 (11) | 0.0055 (11) | 0.0037 (13) |
| C16 | 0.0240 (14) | 0.0356 (16) | 0.0281 (16) | −0.0089 (11) | 0.0066 (12) | −0.0044 (13) |
| C17 | 0.0209 (13) | 0.0284 (14) | 0.0326 (16) | −0.0046 (11) | 0.0106 (12) | −0.0013 (12) |
| C18 | 0.0336 (16) | 0.0291 (15) | 0.045 (2) | −0.0057 (12) | 0.0159 (14) | −0.0033 (14) |
| C19 | 0.0361 (17) | 0.0262 (15) | 0.062 (2) | 0.0008 (13) | 0.0139 (16) | 0.0051 (15) |
| C20 | 0.0260 (15) | 0.0352 (16) | 0.048 (2) | 0.0010 (12) | 0.0036 (14) | 0.0132 (15) |
| C21 | 0.0217 (14) | 0.0340 (15) | 0.0358 (17) | −0.0047 (11) | 0.0040 (12) | 0.0039 (13) |
| C22 | 0.0168 (13) | 0.0256 (13) | 0.0290 (15) | −0.0029 (10) | 0.0065 (11) | 0.0027 (12) |
| C23 | 0.0307 (15) | 0.0281 (15) | 0.0360 (18) | 0.0041 (12) | 0.0036 (13) | −0.0066 (13) |
| C24 | 0.0380 (18) | 0.0304 (16) | 0.053 (2) | −0.0011 (13) | 0.0099 (15) | 0.0012 (15) |
| C25 | 0.047 (2) | 0.049 (2) | 0.0341 (18) | −0.0011 (15) | −0.0030 (15) | 0.0005 (15) |
Geometric parameters (Å, º)
| O1—C1 | 1.322 (3) | C11—H11 | 0.9500 |
| O1—H1 | 1.02 (4) | C11—C12 | 1.354 (4) |
| O2—C1 | 1.230 (3) | C12—H12 | 0.9500 |
| O3—C23 | 1.236 (3) | C12—C13 | 1.402 (5) |
| N1—H1a | 0.8800 | C13—H13 | 0.9500 |
| N1—C5 | 1.365 (3) | C13—C14 | 1.351 (4) |
| N1—C8 | 1.452 (3) | C14—H14 | 0.9500 |
| N2—C23 | 1.326 (4) | C14—C15 | 1.427 (4) |
| N2—C24 | 1.446 (3) | C15—C16 | 1.391 (4) |
| N2—C25 | 1.452 (4) | C16—H16 | 0.9500 |
| C1—C2 | 1.470 (4) | C16—C17 | 1.392 (4) |
| C2—C3 | 1.399 (4) | C17—C18 | 1.424 (4) |
| C2—C7 | 1.393 (3) | C17—C22 | 1.439 (4) |
| C3—H3 | 0.9500 | C18—H18 | 0.9500 |
| C3—C4 | 1.368 (4) | C18—C19 | 1.355 (4) |
| C4—H4 | 0.9500 | C19—H19 | 0.9500 |
| C4—C5 | 1.410 (3) | C19—C20 | 1.407 (4) |
| C5—C6 | 1.405 (4) | C20—H20 | 0.9500 |
| C6—H6 | 0.9500 | C20—C21 | 1.365 (4) |
| C6—C7 | 1.376 (4) | C21—H21 | 0.9500 |
| C7—H7 | 0.9500 | C21—C22 | 1.426 (4) |
| C8—H8a | 0.9900 | C23—H23 | 0.9500 |
| C8—H8b | 0.9900 | C24—H24a | 0.9800 |
| C8—C9 | 1.514 (4) | C24—H24b | 0.9800 |
| C9—C10 | 1.408 (4) | C24—H24c | 0.9800 |
| C9—C22 | 1.406 (3) | C25—H25a | 0.9800 |
| C10—C11 | 1.427 (4) | C25—H25b | 0.9800 |
| C10—C15 | 1.437 (4) | C25—H25c | 0.9800 |
| H1—O1—C1 | 114 (2) | H13—C13—C12 | 119.91 (18) |
| C5—N1—H1a | 118.07 (14) | C14—C13—C12 | 120.2 (3) |
| C8—N1—H1a | 118.07 (14) | C14—C13—H13 | 119.91 (19) |
| C8—N1—C5 | 123.9 (2) | H14—C14—C13 | 119.40 (19) |
| C24—N2—C23 | 120.4 (2) | C15—C14—C13 | 121.2 (3) |
| C25—N2—C23 | 121.1 (2) | C15—C14—H14 | 119.40 (18) |
| C25—N2—C24 | 118.6 (2) | C14—C15—C10 | 118.9 (3) |
| O2—C1—O1 | 122.2 (3) | C16—C15—C10 | 119.2 (2) |
| C2—C1—O1 | 114.4 (2) | C16—C15—C14 | 121.9 (3) |
| C2—C1—O2 | 123.4 (2) | H16—C16—C15 | 119.03 (16) |
| C3—C2—C1 | 119.8 (2) | C17—C16—C15 | 121.9 (2) |
| C7—C2—C1 | 122.1 (2) | C17—C16—H16 | 119.03 (16) |
| C7—C2—C3 | 118.1 (2) | C18—C17—C16 | 121.4 (3) |
| H3—C3—C2 | 119.41 (15) | C22—C17—C16 | 119.2 (2) |
| C4—C3—C2 | 121.2 (2) | C22—C17—C18 | 119.4 (2) |
| C4—C3—H3 | 119.41 (16) | H18—C18—C17 | 119.59 (17) |
| H4—C4—C3 | 119.59 (16) | C19—C18—C17 | 120.8 (3) |
| C5—C4—C3 | 120.8 (2) | C19—C18—H18 | 119.59 (17) |
| C5—C4—H4 | 119.59 (15) | H19—C19—C18 | 119.81 (17) |
| C4—C5—N1 | 119.4 (2) | C20—C19—C18 | 120.4 (3) |
| C6—C5—N1 | 122.6 (2) | C20—C19—H19 | 119.81 (17) |
| C6—C5—C4 | 118.0 (2) | H20—C20—C19 | 119.60 (17) |
| H6—C6—C5 | 119.79 (15) | C21—C20—C19 | 120.8 (3) |
| C7—C6—C5 | 120.4 (2) | C21—C20—H20 | 119.60 (18) |
| C7—C6—H6 | 119.79 (15) | H21—C21—C20 | 119.32 (18) |
| C6—C7—C2 | 121.5 (2) | C22—C21—C20 | 121.4 (3) |
| H7—C7—C2 | 119.26 (15) | C22—C21—H21 | 119.32 (16) |
| H7—C7—C6 | 119.26 (15) | C17—C22—C9 | 119.6 (2) |
| H8a—C8—N1 | 109.85 (14) | C21—C22—C9 | 123.2 (2) |
| H8b—C8—N1 | 109.85 (14) | C21—C22—C17 | 117.2 (2) |
| H8b—C8—H8a | 108.3 | N2—C23—O3 | 125.1 (3) |
| C9—C8—N1 | 109.2 (2) | H23—C23—O3 | 117.46 (17) |
| C9—C8—H8a | 109.85 (14) | H23—C23—N2 | 117.46 (16) |
| C9—C8—H8b | 109.85 (14) | H24a—C24—N2 | 109.5 |
| C10—C9—C8 | 120.7 (2) | H24b—C24—N2 | 109.5 |
| C22—C9—C8 | 118.8 (2) | H24b—C24—H24a | 109.5 |
| C22—C9—C10 | 120.4 (2) | H24c—C24—N2 | 109.5 |
| C11—C10—C9 | 123.2 (2) | H24c—C24—H24a | 109.5 |
| C15—C10—C9 | 119.7 (2) | H24c—C24—H24b | 109.5 |
| C15—C10—C11 | 117.2 (2) | H25a—C25—N2 | 109.5 |
| H11—C11—C10 | 119.22 (16) | H25b—C25—N2 | 109.5 |
| C12—C11—C10 | 121.6 (3) | H25b—C25—H25a | 109.5 |
| C12—C11—H11 | 119.22 (19) | H25c—C25—N2 | 109.5 |
| H12—C12—C11 | 119.52 (19) | H25c—C25—H25a | 109.5 |
| C13—C12—C11 | 121.0 (3) | H25c—C25—H25b | 109.5 |
| C13—C12—H12 | 119.52 (18) |
Hydrogen-bond geometry (Å, º)
Cg5 and Cg7 are the centroids of the 10-membered ring system C9–C22 and of the 14-membered anthracene moiety, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O3 | 1.02 (4) | 1.59 (4) | 2.590 (3) | 167 (4) |
| N1—H1A···O2i | 0.88 (1) | 2.13 (1) | 2.973 (3) | 160 (1) |
| C18—H18···O3ii | 0.95 (1) | 2.40 (1) | 3.277 (4) | 154 (1) |
| C6—H6···Cg7iii | 0.95 | 2.80 (1) | 3.552 (2) | 137 (1) |
| C7—H7···Cg5iii | 0.95 | 2.99 (1) | 3.646 (3) | 138 (1) |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y+1/2, −z+1/2.
Funding Statement
This work was funded by University Grant Commission, India grant .
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989020005393/wm5548sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989020005393/wm5548Isup2.hkl
CCDC reference: 1982147
Additional supporting information: crystallographic information; 3D view; checkCIF report