In molecule of the title compound, the benzene ring is inclined to the mean plane of the anthracene ring system (r.m.s. deviation = 0.024 Å) by 75.21 (9)°. In the crystal, a classical carboxylic acid inversion dimer is formed enclosing an 
(8) ring motif.
Keywords: crystal structure, 4-aminobenzoic acid (PABA), 9-anthraldehyde, hydrogen bonding, C—H⋯π interactions
Abstract
In the molecule of the title anthracene derivative, C22H17NO2, the benzene ring is inclined to the mean plane of the anthracene ring system (r.m.s. deviation = 0.024 Å) by 75.21 (9)°. In the crystal, molecules are linked by pairs of O—H⋯O hydrogen bonds, forming classical carboxylic acid inversion dimers with an R 2 2(8) ring motif. The dimers are linked by C—H⋯π interactions, forming a supramolecular framework.
Chemical context
Anthraldehyde has been used in the synthesis of several Schiff base compounds that exhibit fluorescent properties as a result of strong π–π conjugation (Asiri et al., 2011 ▸; Pavitha et al., 2017 ▸). Many complexes synthesized using anthraldehyde have shown remarkable sensing properties and have been used as chemo sensors (Obali & Ucan, 2012 ▸; Zhou et al., 2012 ▸). Schiff base compounds are also of interest because of their biological applications, which include antibacterial, anticancer and antiviral (Asiri & Khan, 2010 ▸; Cheng et al., 2010 ▸) activities. Herein, we report on the crystal and molecular structures of the title Schiff base compound, 4-{[(anthracen-9-yl)methyl]amino}benzoic acid, synthesized via reaction of 9-anthraldehyde with 4-aminobenzoic acid (PABA) followed by reduction with sodium borohydride.
Structural commentary
The molecular structure of the title compound is illustrated in Fig. 1 ▸. The molecule is non-planar, with the benzene ring (C2–C7) being inclined to the mean plane of the anthracene ring system (C9–C22; r.m.s. deviation = 0.024 Å) by 75.21 (9)°, and the torsional angle of the bridge, C5—N1—C8—C9, is 142.6 (2)°. The C8—N1 bond length of 1.457 (3) Å, is comparable to the C—N bond-length values obtained for the similar ligand 5-[(anthracen-9-ylmethyl)amino]isophthalic acid (see §5. Database survey).
Figure 1.
The molecular structure of the tittle compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
The C1=O2 and C1—O1 bond lengths of 1.238 (3) and 1.325 (3) Å, respectively, are in the expected ranges (Cambridge Structural Database; Groom et al., 2016 ▸).
Supramolecular features
In the crystal, a classical carboxylic acid inversion dimer is formed enclosing an (8) ring motif (Table 1 ▸ and Fig. 2 ▸). The dimers pack along the a-axis direction in a herringbone fashion. They are linked by a series of C—H⋯π interactions (Table 1 ▸ and Fig. 3 ▸), forming a supramolecular three-dimensional structure. The NH hydrogen atom (H1A) is not involved in hydrogen bonding but is directed towards the benzene ring (C2–C7). Approximate geometrical details of this weak N—H⋯π interaction are given in Table 1 ▸.
Table 1. Hydrogen-bond geometry (Å, °).
Cg1, Cg2, and Cg4 are the centroids of the C2–C7, C9/C10/C15–C17/C22 and C17–C22 rings, respectively. Approximative geometrical parameters are given for the weak N—H..π interaction.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O1—H1⋯O2i | 1.05 (4) | 1.58 (3) | 2.621 (3) | 172 (3) |
| N1—H1A⋯Cg1ii | 0.93 (3) | 3.49 | 4.140 | 129 |
| C4—H4⋯Cg4iii | 0.93 | 2.98 (1) | 3.752 (3) | 141 (1) |
| C6—H6⋯Cg1ii | 0.93 | 2.69 (1) | 3.410 (3) | 135 (1) |
| C16—H16⋯Cg4iv | 0.93 | 2.83 (1) | 3.644 (3) | 147 (1) |
| C18—H18⋯Cg2iv | 0.93 | 2.69 (1) | 3.452 (3) | 140 (1) |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
.
Figure 2.
A partial view along the b axis of crystal packing of the title compound. The hydrogen bonds (Table 1 ▸) are shown as dashed lines.
Figure 3.
A view along the b axis of crystal packing of the title compound. The O—H⋯O hydrogen bonds and the C—H⋯π interactions are indicated by dashed lines (Table 1 ▸). For clarity, only the H atoms (grey balls) involved in these interactions have been included.
Hirshfeld analysis
The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009 ▸) and the associated two-dimensional fingerprint plots (McKinnon et al., 2007 ▸) were performed with CrystalExplorer17 (Turner et al., 2017 ▸). The Hirshfeld surfaces are colour-mapped with the normalized contact distance, d norm, 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 Hirshfeld surface of the title compound mapped over d norm, in the colour range −0.7519 to 1.6997 a.u., is given in Fig. 4 ▸. The positions of the strong O—H⋯O hydrogen bonds are indicated by the red regions on the Hirshfeld surface.
Figure 4.
The Hirshfeld surface of the title compound mapped over d norm, in the colour range −0.7519 to 1.6997 a.u..
The two-dimensional fingerprint plots are given in Fig. 5 ▸. They reveal that the principal contributions to the overall surface involve H⋯H contacts at 42.7% (Fig. 5 ▸ b), followed by C⋯H/H⋯C contacts at 40.0% (Fig. 5 ▸ c) and O⋯H/H⋯O contacts at 12.3% (Fig. 5 ▸ d). Apart from the C⋯C contacts, contributing 2.1%, all other atom⋯atom contact contributions are negligible.
Figure 5.
(a) The two-dimensional fingerprint plots of the title compound, and delineated into (b) H⋯H (42.7%), (c) C⋯H/H⋯C (40.0%) and (d) O⋯H/H⋯O (12.3%) contacts.
Database survey
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 (see supporting information file S1), all of which concern polymeric metal complexes of the ligand 5-[(anthracen-9-ylmethyl)amino]isophthalic acid; for example, a series of four gadolinium coordination polymers (CSD refcodes VOLSOG, VOLSUM, VOLTAT, VOLTIB; Singh et al., 2014 ▸). The bridging C—N bond length varies from ca.1.389 to 1.494 Å, compared to the C8—N1 bond length of 1.457 (3) Å in the title compound.
A search for the 1-(anthracen-9-yl)-N-phenylmethanimine skeleton gave 21 hits (see supporting information file S2), none of which involve a benzoic acid moiety.
Synthesis and crystallization
4-Aminobenzoic acid (0.33 g, 2.42 mmol) was added to a solution of 9-anthraldehyde (0.5 g, 2.42 mmol) dissolved in ethanol and the whole mixture was heated at 343 K under reflux for 5–6 h. The mixture was then stirred for a further 10 h at room temperature to obtain a yellow precipitate of the new product, which was monitored through TLC. The yellow precipitate, which was then air dried, was obtained in 76% yield. This was further reduced with sodium borohydride taken in excess (0.183 g, 4.84 mmol) by maintaining the temperature at 277–278 K until the colour of the precipitate had changed from bright yellow to dull yellow. The precipitate was filtered, washed with water and acidified with acetic acid. The product thus obtained was dissolved in hot ethanol and kept for crystallization. Block-like pale-yellow crystals of the title compound were obtained after a few days.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. The OH and NH hydrogen atoms were located in a difference-Fourier map and refined freely. The C-bound H atoms were included in calculated positions and allowed to ride on their parent C atom: C—H = 0.93–0.97Å with U iso(H) = 1.2U eq(C).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C22H17NO2 |
| M r | 327.39 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 100 |
| a, b, c (Å) | 14.985 (2), 6.0116 (9), 19.106 (3) |
| β (°) | 106.796 (5) |
| V (Å3) | 1647.7 (4) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.09 |
| Crystal size (mm) | 0.4 × 0.27 × 0.18 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Krause et al., 2015 ▸) |
| T min, T max | 0.629, 0.746 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 25595, 2913, 1975 |
| R int | 0.118 |
| (sin θ/λ)max (Å−1) | 0.596 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.048, 0.141, 1.12 |
| No. of reflections | 2913 |
| No. of parameters | 235 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.38, −0.32 |
Supplementary Material
Crystal structure: contains datablock(s) Global, I. DOI: 10.1107/S2056989019016207/su5532sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019016207/su5532Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989019016207/su5532Isup5.cml
CSD search S1. DOI: 10.1107/S2056989019016207/su5532sup3.pdf
CSD search S2. DOI: 10.1107/S2056989019016207/su5532sup4.pdf
CCDC reference: 1969448
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors are grateful to the Department of Chemistry, Langat Singh College, B. R. A. Bihar University, Muzaffarpur, India, for providing laboratory facilities.
supplementary crystallographic information
Crystal data
| C22H17NO2 | F(000) = 688.3239 |
| Mr = 327.39 | Dx = 1.320 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 14.985 (2) Å | Cell parameters from 3139 reflections |
| b = 6.0116 (9) Å | θ = 3.1–28.2° |
| c = 19.106 (3) Å | µ = 0.09 mm−1 |
| β = 106.796 (5)° | T = 100 K |
| V = 1647.7 (4) Å3 | Block, pale-yellow |
| Z = 4 | 0.4 × 0.27 × 0.18 mm |
Data collection
| Bruker APEXII CCD diffractometer | 1975 reflections with I > 2σ(I) |
| φ and ω scans | Rint = 0.118 |
| Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 25.1°, θmin = 2.8° |
| Tmin = 0.629, Tmax = 0.746 | h = −20→20 |
| 25595 measured reflections | k = −8→8 |
| 2913 independent reflections | l = −25→25 |
Refinement
| Refinement on F2 | 29 constraints |
| Least-squares matrix: full | Primary atom site location: iterative |
| R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.141 | w = 1/[σ2(Fo2) + (0.0452P)2 + 0.9105P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.12 | (Δ/σ)max = 0.0003 |
| 2913 reflections | Δρmax = 0.38 e Å−3 |
| 235 parameters | Δρmin = −0.32 e Å−3 |
| 0 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.47155 (12) | 0.7404 (3) | 0.95012 (10) | 0.0304 (5) | |
| O2 | 0.57543 (12) | 1.0125 (3) | 0.95315 (10) | 0.0317 (5) | |
| N1 | 0.66609 (14) | 0.3342 (4) | 0.72544 (12) | 0.0252 (5) | |
| C1 | 0.54000 (17) | 0.8318 (4) | 0.92904 (14) | 0.0238 (6) | |
| C2 | 0.57055 (16) | 0.7035 (4) | 0.87497 (13) | 0.0212 (6) | |
| C3 | 0.63813 (16) | 0.7902 (4) | 0.84570 (14) | 0.0230 (6) | |
| H3 | 0.66266 (16) | 0.9303 (4) | 0.86054 (14) | 0.0276 (7)* | |
| C4 | 0.66973 (17) | 0.6741 (4) | 0.79531 (13) | 0.0222 (6) | |
| H4 | 0.71436 (17) | 0.7367 (4) | 0.77612 (13) | 0.0266 (7)* | |
| C5 | 0.63421 (16) | 0.4606 (4) | 0.77302 (13) | 0.0209 (6) | |
| C6 | 0.56515 (17) | 0.3731 (4) | 0.80193 (13) | 0.0224 (6) | |
| H6 | 0.53997 (17) | 0.2335 (4) | 0.78701 (13) | 0.0269 (7)* | |
| C7 | 0.53463 (16) | 0.4920 (4) | 0.85202 (13) | 0.0215 (6) | |
| H7 | 0.48944 (16) | 0.4312 (4) | 0.87096 (13) | 0.0258 (7)* | |
| C8 | 0.74688 (17) | 0.3903 (4) | 0.70105 (14) | 0.0243 (6) | |
| H8a | 0.72642 (17) | 0.4653 (4) | 0.65418 (14) | 0.0291 (7)* | |
| H8b | 0.78696 (17) | 0.4913 (4) | 0.73586 (14) | 0.0291 (7)* | |
| C9 | 0.80133 (16) | 0.1835 (4) | 0.69386 (13) | 0.0208 (6) | |
| C10 | 0.80253 (16) | 0.1014 (4) | 0.62496 (13) | 0.0204 (6) | |
| C11 | 0.75646 (17) | 0.2083 (4) | 0.55691 (14) | 0.0257 (6) | |
| H11 | 0.72308 (17) | 0.3384 (4) | 0.55740 (14) | 0.0308 (7)* | |
| C12 | 0.76034 (18) | 0.1242 (5) | 0.49175 (14) | 0.0294 (7) | |
| H12 | 0.72945 (18) | 0.1972 (5) | 0.44864 (14) | 0.0353 (8)* | |
| C13 | 0.81084 (18) | −0.0732 (5) | 0.48869 (15) | 0.0310 (7) | |
| H13 | 0.81360 (18) | −0.1278 (5) | 0.44382 (15) | 0.0372 (8)* | |
| C14 | 0.85503 (17) | −0.1822 (4) | 0.55102 (14) | 0.0269 (6) | |
| H14 | 0.88740 (17) | −0.3124 (4) | 0.54841 (14) | 0.0322 (7)* | |
| C15 | 0.85289 (16) | −0.1007 (4) | 0.62098 (14) | 0.0216 (6) | |
| C16 | 0.89943 (16) | −0.2114 (4) | 0.68500 (14) | 0.0225 (6) | |
| H16 | 0.93082 (16) | −0.3429 (4) | 0.68203 (14) | 0.0270 (7)* | |
| C17 | 0.90025 (16) | −0.1302 (4) | 0.75358 (13) | 0.0202 (6) | |
| C18 | 0.94936 (16) | −0.2430 (4) | 0.81929 (14) | 0.0255 (6) | |
| H18 | 0.98095 (16) | −0.3741 (4) | 0.81619 (14) | 0.0307 (7)* | |
| C19 | 0.95099 (18) | −0.1630 (4) | 0.88627 (15) | 0.0289 (7) | |
| H19 | 0.98374 (18) | −0.2383 (4) | 0.92840 (15) | 0.0347 (8)* | |
| C20 | 0.90250 (17) | 0.0354 (4) | 0.89133 (15) | 0.0287 (6) | |
| H20 | 0.90346 (17) | 0.0897 (4) | 0.93712 (15) | 0.0344 (8)* | |
| C21 | 0.85437 (17) | 0.1482 (4) | 0.83019 (14) | 0.0243 (6) | |
| H21 | 0.82321 (17) | 0.2784 (4) | 0.83510 (14) | 0.0291 (7)* | |
| C22 | 0.85075 (16) | 0.0706 (4) | 0.75862 (14) | 0.0204 (6) | |
| H1 | 0.457 (2) | 0.850 (6) | 0.9884 (19) | 0.074 (11)* | |
| H1a | 0.635 (2) | 0.201 (5) | 0.7113 (15) | 0.042 (9)* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0321 (10) | 0.0298 (10) | 0.0357 (12) | −0.0061 (8) | 0.0198 (9) | −0.0083 (9) |
| O2 | 0.0368 (11) | 0.0274 (10) | 0.0352 (12) | −0.0070 (9) | 0.0172 (9) | −0.0115 (9) |
| N1 | 0.0215 (12) | 0.0251 (12) | 0.0322 (14) | −0.0041 (10) | 0.0127 (10) | −0.0071 (10) |
| C1 | 0.0234 (14) | 0.0238 (14) | 0.0239 (15) | 0.0007 (11) | 0.0065 (11) | 0.0001 (11) |
| C2 | 0.0200 (13) | 0.0223 (13) | 0.0209 (14) | 0.0021 (11) | 0.0053 (11) | −0.0011 (11) |
| C3 | 0.0204 (13) | 0.0206 (13) | 0.0275 (15) | 0.0013 (11) | 0.0059 (11) | −0.0024 (11) |
| C4 | 0.0197 (13) | 0.0236 (13) | 0.0242 (14) | −0.0003 (11) | 0.0078 (11) | 0.0018 (11) |
| C5 | 0.0195 (13) | 0.0207 (13) | 0.0219 (14) | 0.0026 (10) | 0.0051 (11) | 0.0004 (11) |
| C6 | 0.0215 (13) | 0.0194 (13) | 0.0251 (15) | 0.0012 (11) | 0.0050 (11) | −0.0012 (11) |
| C7 | 0.0185 (13) | 0.0229 (13) | 0.0230 (14) | 0.0015 (11) | 0.0058 (11) | 0.0036 (11) |
| C8 | 0.0234 (13) | 0.0218 (13) | 0.0295 (16) | −0.0009 (11) | 0.0105 (12) | −0.0011 (11) |
| C9 | 0.0193 (13) | 0.0202 (13) | 0.0241 (14) | −0.0013 (10) | 0.0081 (11) | −0.0007 (11) |
| C10 | 0.0147 (12) | 0.0227 (13) | 0.0242 (15) | −0.0019 (10) | 0.0063 (11) | −0.0005 (11) |
| C11 | 0.0216 (13) | 0.0277 (14) | 0.0279 (15) | 0.0013 (11) | 0.0076 (11) | 0.0009 (12) |
| C12 | 0.0250 (14) | 0.0397 (16) | 0.0215 (15) | 0.0021 (12) | 0.0037 (12) | 0.0020 (12) |
| C13 | 0.0267 (14) | 0.0393 (16) | 0.0258 (16) | 0.0018 (13) | 0.0057 (12) | −0.0067 (13) |
| C14 | 0.0238 (13) | 0.0287 (14) | 0.0276 (15) | 0.0006 (12) | 0.0066 (12) | −0.0089 (12) |
| C15 | 0.0170 (12) | 0.0235 (13) | 0.0239 (15) | −0.0030 (10) | 0.0054 (11) | −0.0043 (11) |
| C16 | 0.0202 (13) | 0.0190 (13) | 0.0297 (15) | 0.0000 (11) | 0.0094 (11) | −0.0029 (11) |
| C17 | 0.0171 (12) | 0.0212 (13) | 0.0235 (14) | −0.0022 (10) | 0.0076 (11) | 0.0009 (11) |
| C18 | 0.0195 (13) | 0.0249 (14) | 0.0318 (16) | −0.0010 (11) | 0.0066 (11) | 0.0024 (12) |
| C19 | 0.0234 (14) | 0.0345 (16) | 0.0272 (16) | −0.0043 (12) | 0.0047 (11) | 0.0064 (12) |
| C20 | 0.0285 (15) | 0.0338 (15) | 0.0245 (16) | −0.0051 (12) | 0.0087 (12) | −0.0032 (12) |
| C21 | 0.0216 (13) | 0.0261 (14) | 0.0268 (15) | −0.0023 (11) | 0.0096 (11) | −0.0029 (12) |
| C22 | 0.0181 (12) | 0.0203 (13) | 0.0242 (14) | −0.0054 (10) | 0.0085 (11) | −0.0030 (11) |
Geometric parameters (Å, º)
| O1—C1 | 1.325 (3) | C10—C15 | 1.443 (3) |
| O1—H1 | 1.05 (4) | C11—H11 | 0.9300 |
| O2—C1 | 1.238 (3) | C11—C12 | 1.360 (3) |
| N1—C5 | 1.372 (3) | C12—H12 | 0.9300 |
| N1—C8 | 1.457 (3) | C12—C13 | 1.418 (4) |
| N1—H1a | 0.92 (3) | C13—H13 | 0.9300 |
| C1—C2 | 1.465 (3) | C13—C14 | 1.353 (4) |
| C2—C3 | 1.392 (3) | C14—H14 | 0.9300 |
| C2—C7 | 1.401 (3) | C14—C15 | 1.433 (3) |
| C3—H3 | 0.9300 | C15—C16 | 1.390 (3) |
| C3—C4 | 1.379 (3) | C16—H16 | 0.9300 |
| C4—H4 | 0.9300 | C16—C17 | 1.395 (3) |
| C4—C5 | 1.408 (3) | C17—C18 | 1.429 (3) |
| C5—C6 | 1.408 (3) | C17—C22 | 1.435 (3) |
| C6—H6 | 0.9300 | C18—H18 | 0.9300 |
| C6—C7 | 1.375 (3) | C18—C19 | 1.360 (4) |
| C7—H7 | 0.9300 | C19—H19 | 0.9300 |
| C8—H8a | 0.9700 | C19—C20 | 1.414 (4) |
| C8—H8b | 0.9700 | C20—H20 | 0.9300 |
| C8—C9 | 1.515 (3) | C20—C21 | 1.363 (3) |
| C9—C10 | 1.411 (3) | C21—H21 | 0.9300 |
| C9—C22 | 1.418 (3) | C21—C22 | 1.431 (3) |
| C10—C11 | 1.436 (3) | ||
| H1—O1—C1 | 106.6 (18) | H11—C11—C10 | 119.13 (14) |
| C8—N1—C5 | 124.4 (2) | C12—C11—C10 | 121.7 (2) |
| H1a—N1—C5 | 115.7 (18) | C12—C11—H11 | 119.13 (16) |
| H1a—N1—C8 | 119.8 (18) | H12—C12—C11 | 119.57 (16) |
| O2—C1—O1 | 122.5 (2) | C13—C12—C11 | 120.9 (3) |
| C2—C1—O1 | 115.1 (2) | C13—C12—H12 | 119.57 (16) |
| C2—C1—O2 | 122.5 (2) | H13—C13—C12 | 119.99 (16) |
| C3—C2—C1 | 119.9 (2) | C14—C13—C12 | 120.0 (3) |
| C7—C2—C1 | 121.9 (2) | C14—C13—H13 | 119.99 (16) |
| C7—C2—C3 | 118.2 (2) | H14—C14—C13 | 119.39 (16) |
| H3—C3—C2 | 119.07 (15) | C15—C14—C13 | 121.2 (2) |
| C4—C3—C2 | 121.9 (2) | C15—C14—H14 | 119.39 (15) |
| C4—C3—H3 | 119.07 (15) | C14—C15—C10 | 119.3 (2) |
| H4—C4—C3 | 120.11 (15) | C16—C15—C10 | 119.6 (2) |
| C5—C4—C3 | 119.8 (2) | C16—C15—C14 | 121.1 (2) |
| C5—C4—H4 | 120.11 (14) | H16—C16—C15 | 119.16 (14) |
| C4—C5—N1 | 122.1 (2) | C17—C16—C15 | 121.7 (2) |
| C6—C5—N1 | 119.3 (2) | C17—C16—H16 | 119.16 (14) |
| C6—C5—C4 | 118.6 (2) | C18—C17—C16 | 121.5 (2) |
| H6—C6—C5 | 119.71 (14) | C22—C17—C16 | 119.5 (2) |
| C7—C6—C5 | 120.6 (2) | C22—C17—C18 | 119.0 (2) |
| C7—C6—H6 | 119.71 (15) | H18—C18—C17 | 119.22 (15) |
| C6—C7—C2 | 121.0 (2) | C19—C18—C17 | 121.6 (2) |
| H7—C7—C2 | 119.49 (14) | C19—C18—H18 | 119.22 (16) |
| H7—C7—C6 | 119.49 (15) | H19—C19—C18 | 120.26 (16) |
| H8a—C8—N1 | 109.44 (13) | C20—C19—C18 | 119.5 (3) |
| H8b—C8—N1 | 109.44 (13) | C20—C19—H19 | 120.26 (16) |
| H8b—C8—H8a | 108.0 | H20—C20—C19 | 119.47 (16) |
| C9—C8—N1 | 111.0 (2) | C21—C20—C19 | 121.1 (3) |
| C9—C8—H8a | 109.44 (14) | C21—C20—H20 | 119.47 (16) |
| C9—C8—H8b | 109.44 (13) | H21—C21—C20 | 119.29 (16) |
| C10—C9—C8 | 121.6 (2) | C22—C21—C20 | 121.4 (2) |
| C22—C9—C8 | 118.2 (2) | C22—C21—H21 | 119.29 (14) |
| C22—C9—C10 | 120.2 (2) | C17—C22—C9 | 119.6 (2) |
| C11—C10—C9 | 123.8 (2) | C21—C22—C9 | 123.0 (2) |
| C15—C10—C9 | 119.4 (2) | C21—C22—C17 | 117.4 (2) |
| C15—C10—C11 | 116.8 (2) | ||
| C8—N1—C5—C4 | 8.8 (4) | C9—C10—C11—C12 | 179.3 (3) |
| C8—N1—C5—C6 | −169.8 (2) | C15—C10—C11—C12 | −0.3 (4) |
| C5—N1—C8—C9 | 142.6 (2) | C9—C10—C15—C14 | −179.2 (2) |
| O1—C1—C2—C3 | 176.1 (2) | C9—C10—C15—C16 | 0.0 (4) |
| O1—C1—C2—C7 | −4.8 (4) | C11—C10—C15—C14 | 0.4 (3) |
| O2—C1—C2—C3 | −3.8 (4) | C11—C10—C15—C16 | 179.6 (2) |
| O2—C1—C2—C7 | 175.3 (2) | C10—C11—C12—C13 | −0.3 (4) |
| C1—C2—C3—C4 | 179.2 (2) | C11—C12—C13—C14 | 0.8 (4) |
| C7—C2—C3—C4 | 0.1 (4) | C12—C13—C14—C15 | −0.7 (4) |
| C1—C2—C7—C6 | −179.1 (2) | C13—C14—C15—C10 | 0.1 (4) |
| C3—C2—C7—C6 | 0.0 (4) | C13—C14—C15—C16 | −179.1 (3) |
| C2—C3—C4—C5 | −0.8 (4) | C10—C15—C16—C17 | −1.1 (4) |
| C3—C4—C5—N1 | −177.2 (2) | C14—C15—C16—C17 | 178.0 (2) |
| C3—C4—C5—C6 | 1.4 (4) | C15—C16—C17—C18 | −179.1 (2) |
| N1—C5—C6—C7 | 177.3 (2) | C15—C16—C17—C22 | 1.0 (4) |
| C4—C5—C6—C7 | −1.4 (4) | C16—C17—C18—C19 | 179.4 (2) |
| C5—C6—C7—C2 | 0.7 (4) | C22—C17—C18—C19 | −0.7 (4) |
| N1—C8—C9—C10 | 109.5 (3) | C16—C17—C22—C9 | 0.3 (4) |
| N1—C8—C9—C22 | −69.6 (3) | C16—C17—C22—C21 | −179.5 (2) |
| C8—C9—C10—C11 | 2.5 (4) | C18—C17—C22—C9 | −179.7 (2) |
| C8—C9—C10—C15 | −177.9 (2) | C18—C17—C22—C21 | 0.6 (4) |
| C22—C9—C10—C11 | −178.4 (2) | C17—C18—C19—C20 | 0.5 (4) |
| C22—C9—C10—C15 | 1.3 (4) | C18—C19—C20—C21 | −0.2 (4) |
| C8—C9—C22—C17 | 177.8 (2) | C19—C20—C21—C22 | 0.1 (4) |
| C8—C9—C22—C21 | −2.5 (4) | C20—C21—C22—C9 | 179.9 (3) |
| C10—C9—C22—C17 | −1.4 (4) | C20—C21—C22—C17 | −0.4 (4) |
| C10—C9—C22—C21 | 178.3 (2) |
Hydrogen-bond geometry (Å, º)
Cg1, Cg2, and Cg4 are the centroids of the C2–C7, C9/C10/C15–C17/C22 and C17–C22 rings, respectively. Approximative geometrical parameters are given for the weak N—H..π interaction.
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···O2i | 1.05 (4) | 1.58 (3) | 2.621 (3) | 172 (3) |
| N1—H1A···Cg1ii | 0.93 (3) | 3.49 | 4.140 | 129 |
| C4—H4···Cg4iii | 0.93 | 2.98 (1) | 3.752 (3) | 141 (1) |
| C6—H6···Cg1ii | 0.93 | 2.69 (1) | 3.410 (3) | 135 (1) |
| C16—H16···Cg4iv | 0.93 | 2.83 (1) | 3.644 (3) | 147 (1) |
| C18—H18···Cg2iv | 0.93 | 2.69 (1) | 3.452 (3) | 140 (1) |
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y+1, z; (iv) −x+2, y−1/2, −z+3/2.
Funding Statement
This work was funded by University Grants Commisson (India) grant .
References
- Asiri, A. M., Al-Youbi, A. O., Khan, S. A. & Tahir, M. N. (2011). Acta Cryst. E67, o3419. [DOI] [PMC free article] [PubMed]
- Asiri, A. M. & Khan, S. A. (2010). Molecules, 15, 6850–6858. [DOI] [PMC free article] [PubMed]
- Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59–75. [DOI] [PMC free article] [PubMed]
- Bruker (2016). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
- Cheng, L. X., Tang, J. J., Luo, H., Jin, X.-L., Dai, F., Yang, J., Qian, Y.-P., Li, X.-Z. & Zhou, B. (2010). Bioorg. Med. Chem. Lett. 20, 2417–2420. [DOI] [PubMed]
- Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.
- Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. [DOI] [PMC free article] [PubMed]
- Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. [DOI] [PMC free article] [PubMed]
- 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.
- McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. [DOI] [PubMed]
- Obali, A. Y. & Ucan, H. I. (2012). J. Fluoresc. 22, 1357–1370. [DOI] [PubMed]
- Pavitha, P., Prashanth, J., Ramu, G., Ramesh, G., Mamatha, K. & Reddy, B. V. (2017). J. Mol. Struct. 1147, 406–426.
- Singh, R., Mrozinski, J. & Bharadwaj, P. K. (2014). Cryst. Growth Des. 14, 3623–3633.
- Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32.
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
- Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. http://hirshfeldsurface.net
- Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.
- Zhou, Y., Zhou, H., Zhang, J., Zhang, L. & Niu, J. (2012). Spectrochimica Acta Part A: Mol. Biomol. Spect. 98, 14–17. [DOI] [PubMed]
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) Global, I. DOI: 10.1107/S2056989019016207/su5532sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989019016207/su5532Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989019016207/su5532Isup5.cml
CSD search S1. DOI: 10.1107/S2056989019016207/su5532sup3.pdf
CSD search S2. DOI: 10.1107/S2056989019016207/su5532sup4.pdf
CCDC reference: 1969448
Additional supporting information: crystallographic information; 3D view; checkCIF report