Crystal structure of an aceto­nitrile solvate of 2-(3,4,5-triphen­ylphen­yl)acetic acid

Seidel, P.; Gottwald, F.; Meier, E.; Mazik, M.

doi:10.1107/S2056989024009976

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Volume 80| Part 11| November 2024| Pages 1198-1201

https://doi.org/10.1107/S2056989024009976

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Crystal structure of an acetonitrile solvate of 2-(3,4,5-triphenylphenyl)acetic acid

Pierre Seidel,^a Franziska Gottwald,^a Eric Meier ^a and Monika Mazik ^a ^*

^aInstitut für Organische Chemie, Technische Universität Bergakademie, Freiberg, Leipziger Str. 29, 09599 Freiberg/Sachsen, Germany
^*Correspondence e-mail: monika.mazik@chemie.tu-freiberg.de

Edited by J. Reibenspies, Texas A & M University, USA (Received 6 September 2024; accepted 11 October 2024; online 24 October 2024)

Crystal growth of 2-(3,4,5-triphenylphenyl)acetic acid (1) from acetonitrile yields a monosolvate, C₂₆H₂₀O₂·CH₃CN, of the space group P1. In the crystal, the title molecule adopts a conformation in which the three phenyl rings are arranged in a paddlewheel-like fashion around the central arene ring and the carboxyl residue is oriented nearly perpendicular to the plane of this benzene ring. Inversion-symmetric dimers of O—H⋯O-bonded molecules of 1 represent the basic supramolecular entities of the crystal structure. These dimeric molecular units are further linked by C—H⋯O=C bonds to form one-dimensional supramolecular aggregates running along the crystallographic [111] direction. Weak C_aryl—H⋯N interactions occur between the molecules of 1 and acetonitrile.

Keywords: carboxylic acid dimers; C—H⋯π interactions; acetonitrile solvate; crystal structure.

CCDC reference: 2391130

1. Chemical context

Phenylacetic acid (PAA) and its derivatives have a wide range of biological activities (Cook, 2019 ; Jiao et al., 2022 ; Perez et al., 2023 ). It is important to note that this class of compounds has played an important role in the development of numerous drugs, for example as a building block of drug molecules or as a starting material for their syntheses (Treves & Testa, 1952 ; Vardanyan & Hruby, 2006 ). Examples include drugs such as diclofenac, ibuprofen, flurbiprofen, cyclopentolate and atenolol. They have a wide range of uses, including non-steroidal anti-inflammatory drugs, analgesics, anticancer agents, mydriatics and cycloplegics, among others. Compounds bearing one or two phenyl substituents on the benzene ring of PAA have been reported to have anti-tumor activity (Lade et al., 2023 ) and some have been proposed as candidates for the treatment of Alzheimer's disease (Wilson et al., 2015 ). The synthesis of new derivatives of phenylacetic acid is of great importance due to their interesting properties and the possibility of their wide application.

The title compound, which bears three phenyl substituents in positions 3, 4 and 5 of the benzene ring of PAA, has been prepared by us as a compound with potentially valuable biological activities and with the ability to act as a starting material for various functionalizations (Mazik & Seidel, 2024 ). Crystallization of this compound from acetonitrile yielded a solvate, the crystal structure of which is described in this article.

2. Structural commentary

The title compound 2-(3,4,5-triphenylphenyl)acetic acid (1) forms a solvate with acetonitrile, which crystallizes in the space group P $[\overline{1}]$ and contains one formula unit of each molecular species within its asymmetric unit (see Fig. 1). A slight disorder of the solvent is observed, as its methyl hydrogen atoms occupy two positions in a roughly 50:50 distribution. The three phenyl substituents attached to the central benzene ring of 1 (A, C1–C6) uniformly adopt a tilted orientation with respect to the plane of this ring, resulting in a molecular geometry that resembles a paddlewheel. The inclination angles of the aromatic planes in relation to the central ring (A) amount to 46.39 (6)° (ring B, C9–C14), 59.72 (6)° (ring C, C15–C20) and 56.17 (6)° (ring D, C21–C26), respectively. The plane through the carboxyl group of the molecular side arm is oriented nearly perpendicular [84.9 (1)°] with respect to the central arene ring.

Figure 1
Perspective view of the molecular structure of 1·CH₃CN including the atom labeling and ring specification. Atomic displacement ellipsoids are drawn at the 50% probability level. Broken gray lines indicate the second position of the disordered methyl hydrogen atoms of the solvent.

3. Supramolecular features

The most dominant non-covalent interactions within the crystal structure (see Fig. 2 and Table 1) are classical hydrogen bonds between the carboxyl moieties of the inversion-related molecules [d(H1⋯O2) = 1.62 (2) Å, O—H⋯O = 174 (2)°], forming a cyclic synthon of the graph set R₂²(8) (Etter et al. 1990 ; Bernstein et al., 1995 ; for a discussion on supramolecular synthons in crystal engineering, including those formed by carboxyl groups, see: Desiraju, 1995 ). As shown in Fig. 3, these dimers are connected along the [111] direction by pairs of C—H⋯O bonds involving the aryl hydrogen atom H19 and the carbonyl oxygen atom O2 [d = 2.56 Å, C—H⋯O = 163°; for other examples of C—H⋯O bonds, see: Desiraju & Steiner, 1999 ; Desiraju, 2005 ; Mazik et al., 1999a , 2005 , 2010 ; Ebersbach et al., 2023 ]. Consequently, O2 acts as a bifurcated binding site for hydrogen bonding. The solvent molecule appears to be fixed in its position by a weak C—H⋯N bond involving the atom H2 of the central arene ring [d = 2.71 Å, C—H⋯N = 150°; for other examples of C—H⋯N bonds, see: Reddy et al., 1996 ; Desiraju & Steiner, 1999; Thalladi et al., 2000a ,b ; Mazik et al., 1999b , 2000a ,b , 2001 , 2005]. Since the peripheries of the one-dimensional supramolecular aggregates are formed by the non-polar units of the host molecules, van der Waals forces contribute significantly to the cohesion of the crystal structure. Moreover, multiple short distances between C—H units and aromatic moieties suggest the presence of C—H⋯π interactions (Nishio et al., 2009 , 2011 ).

Table 1
Geometric data (Å, °) of short intermolecular interactions

Cg(A) and Cg(D) refer to the centers of gravity of the rings C1–C6 and C21–C26, respectively

D—H⋯A/Cg	D—H	H⋯A/Cg	D⋯A/Cg	D—H⋯A/Cg
O1—H1⋯O2ⁱ	1.01 (2)	1.62 (2)	2.624 (1)	174 (2)
C2—H2⋯N1ⁱⁱ	0.95	2.71	3.567 (2)	150
C19—H19⋯O2ⁱⁱⁱ	0.95	2.56	3.477 (1)	163
C7—H7B⋯Cg(D)^iv	0.99	2.97	3.746 (1)	136
C10—H10⋯Cg(A)^v	0.95	2.97	3.509 (1)	119
Symmetry codes: (i) −x, −y, −z + 1; (ii) −x + 1, −y, −z + 1; (iii) −x + 1, −y + 1, −z + 2; (iv) −x, −y + 1, −z + 1; (v) −x + 1, −y + 1, −z + 1.

Figure 2
Excerpt of the chain-like supramolecular aggregates with labeling of atoms involved in O—H⋯O and C—H⋯O/N hydrogen bonding. Color code: red – O; blue – N. Only the major disorder component of the solvent molecules is depicted.

Figure 3
Packing diagram of the structure viewed along the [111] direction (parallel to the propagation of the supramolecular chains). Hydrogen atoms excluded from hydrogen bonding are omitted for clarity. Dashed lines symbolize the cyclic hydrogen-bond motif between carboxyl functionalities. Color code: red – O; blue – N.

4. Database survey

Based on the search in the Cambridge Structural Database (CSD, Version 5.45, update June 2024; Groom et al., 2016 ) for phenylacetic acid and its derivatives with one to five phenyl substituents on the benzene ring, the crystal structures of phenylacetic acid (ZZZMLY01; Hodgson & Asplund, 1991 ) and 4-biphenylacetic acid (KUZWEI; Van Eerdenbrugh et al., 2010 ) were found. The latter compound is a potent non-steroidal anti-inflammatory drug (felbinac; Hosie & Bird, 1994 ). Furthermore, the crystal structures of the complexes of phenylacetic acid with its potassium salt (KHDPAC; Bacon & Curry, 1960 ), benzamide (MECHAF; Chaudhari & Suryaprakash, 2012 ) and hexamethylenetetramine (urotropine) (VIJTIR; Mak et al., 1986 ) are reported. Single crystal structures of complexes of felbinac with tryptamine and 1,2-diphenylethylenediamine are also described (JOZMEQ, Koshima et al., 1998 ; EDOLAL, Imai et al., 2007 ). Similar to 1, in the solvent-free crystal structures with the reference codes ZZZMLY01 and KUZWEI, the carboxy groups of the adjacent molecules form the dimer synthon (Desiraju, 1995). Furthermore, the aromatic cores are linked via edge-to-face C—H⋯π interactions.

5. Synthesis and crystallization

Compound 1 was prepared as previously described (Mazik & Seidel, 2024). Crystallization was carried out from acetonitrile by slow evaporation of the solvent. Crystal habit: colorless, rhombic plates.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All non-hydrogen atoms were refined anisotropically. The hydrogen atom of the carboxyl group (H1) was located in a difference-Fourier map and refined freely. The remaining hydrogen atoms were positioned geometrically and refined isotropically using a riding model, with C—H bond distances of 0.95 Å (arene), 0.98 Å (methyl) and 0.99 Å (methylene). Additionally, their thermal displacement ellipsoids [U_iso(H)] were set to 1.2 U_eq(C) and 1.5 U_eq(C) for arene/methylene and methyl groups, respectively.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₆H₂₀O₂·C₂H₃N
M_r	405.47
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	123
a, b, c (Å)	10.0737 (5), 11.1039 (6), 11.5835 (6)
α, β, γ (°)	107.025 (4), 114.263 (4), 93.898 (4)
V (Å³)	1102.82 (11)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.32 × 0.23 × 0.12

Data collection
Diffractometer	Stoe Stadivari
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	29260, 5839, 4519
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.07
No. of reflections	5839
No. of parameters	286
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.23
Computer programs: X-AREA, X-AREA Recipe, X-RED32 and LANA (Stoe & Cie, 2002 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/3 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), XP in SHELXTL (Sheldrick, 2008 ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Supporting information

CCDC reference: 2391130

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024009976/jy2053sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024009976/jy2053Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989024009976/jy2053Isup3.cml

checkCIF report

Computing details top

2-(3,4,5-Triphenylphenyl)acetic acid acetonitrile monosolvate top

Crystal data top

C₂₆H₂₀O₂·C₂H₃N	Z = 2
M_r = 405.47	F(000) = 428
Triclinic, P1	D_x = 1.221 Mg m⁻³
a = 10.0737 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1039 (6) Å	Cell parameters from 20520 reflections
c = 11.5835 (6) Å	θ = 2.0–31.2°
α = 107.025 (4)°	µ = 0.08 mm⁻¹
β = 114.263 (4)°	T = 123 K
γ = 93.898 (4)°	Irregular, colorless
V = 1102.82 (11) Å³	0.32 × 0.23 × 0.12 mm

Data collection top

Stoe Stadivari diffractometer	4519 reflections with I > 2σ(I)
Radiation source: Primux 50 Mo	R_int = 0.029
Graded multilayer mirror monochromator	θ_max = 29.0°, θ_min = 2.0°
Detector resolution: 5.81 pixels mm^-1	h = −13→13
rotation method, ω scans	k = −14→15
29260 measured reflections	l = −15→14
5839 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0493P)² + 0.1858P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
5839 reflections	Δρ_max = 0.29 e Å⁻³
286 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	−0.07298 (9)	0.05965 (8)	0.36283 (9)	0.0358 (2)
H1	−0.091 (2)	−0.0091 (19)	0.399 (2)	0.078 (6)*
O2	0.13280 (9)	0.12762 (8)	0.55908 (8)	0.03183 (19)
C1	0.22564 (11)	0.34842 (10)	0.52186 (10)	0.0216 (2)
C2	0.36906 (12)	0.33544 (10)	0.54368 (10)	0.0218 (2)
H2	0.382286	0.263815	0.483487	0.026*
C3	0.49456 (11)	0.42462 (10)	0.65156 (10)	0.0201 (2)
C4	0.47611 (11)	0.53195 (10)	0.74027 (10)	0.0193 (2)
C5	0.33056 (11)	0.54609 (10)	0.71808 (10)	0.0201 (2)
C6	0.20807 (11)	0.45380 (10)	0.60987 (10)	0.0216 (2)
H6	0.110351	0.463520	0.596275	0.026*
C7	0.09294 (12)	0.24659 (10)	0.40881 (11)	0.0242 (2)
H7A	0.114936	0.210270	0.331366	0.029*
H7B	0.006185	0.286815	0.378211	0.029*
C8	0.05351 (11)	0.13879 (10)	0.45171 (10)	0.0224 (2)
C9	0.64313 (11)	0.39716 (10)	0.66840 (11)	0.0211 (2)
C10	0.66910 (12)	0.35689 (11)	0.55507 (11)	0.0259 (2)
H10	0.594934	0.353617	0.469893	0.031*
C11	0.80157 (13)	0.32161 (12)	0.56508 (12)	0.0301 (2)
H11	0.817483	0.294114	0.486928	0.036*
C12	0.91069 (13)	0.32630 (12)	0.68844 (12)	0.0290 (2)
H12	1.001067	0.301151	0.695058	0.035*
C13	0.88762 (12)	0.36781 (11)	0.80227 (12)	0.0274 (2)
H13	0.963120	0.372551	0.887470	0.033*
C14	0.75473 (12)	0.40252 (11)	0.79249 (11)	0.0244 (2)
H14	0.739576	0.430200	0.871045	0.029*
C15	0.60663 (11)	0.63167 (10)	0.85467 (10)	0.0208 (2)
C16	0.70629 (12)	0.70122 (10)	0.83003 (11)	0.0249 (2)
H16	0.692565	0.683040	0.739973	0.030*
C17	0.82536 (12)	0.79678 (11)	0.93604 (13)	0.0305 (2)
H17	0.891780	0.844448	0.918032	0.037*
C18	0.84776 (13)	0.82292 (11)	1.06779 (13)	0.0334 (3)
H18	0.929920	0.887786	1.140284	0.040*
C19	0.74974 (13)	0.75402 (12)	1.09360 (12)	0.0315 (3)
H19	0.764585	0.771875	1.183930	0.038*
C20	0.63008 (12)	0.65911 (11)	0.98772 (11)	0.0255 (2)
H20	0.563380	0.612290	1.006140	0.031*
C21	0.30036 (11)	0.65849 (10)	0.80381 (10)	0.0211 (2)
C22	0.35417 (12)	0.78503 (10)	0.82192 (11)	0.0246 (2)
H22	0.416416	0.801271	0.782487	0.029*
C23	0.31780 (13)	0.88733 (11)	0.89682 (12)	0.0293 (2)
H23	0.354078	0.973106	0.907495	0.035*
C24	0.22888 (14)	0.86499 (12)	0.95610 (12)	0.0337 (3)
H24	0.204717	0.935273	1.008130	0.040*
C25	0.17528 (15)	0.74009 (13)	0.93941 (13)	0.0354 (3)
H25	0.114454	0.724663	0.980389	0.042*
C26	0.20969 (13)	0.63725 (11)	0.86329 (12)	0.0280 (2)
H26	0.171302	0.551625	0.851468	0.034*
N1	0.7111 (2)	−0.01405 (16)	0.68515 (17)	0.0758 (5)
C27	0.6123 (2)	0.02633 (15)	0.68979 (15)	0.0529 (4)
C28	0.4872 (2)	0.07793 (19)	0.6979 (2)	0.0655 (5)
H28A	0.406195	0.007112	0.673936	0.098*	0.51 (2)
H28B	0.452431	0.124632	0.634864	0.098*	0.51 (2)
H28C	0.518164	0.137051	0.790284	0.098*	0.51 (2)
H28D	0.399355	0.041271	0.609405	0.098*	0.49 (2)
H28E	0.511169	0.171985	0.724289	0.098*	0.49 (2)
H28F	0.466266	0.055539	0.765390	0.098*	0.49 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0314 (4)	0.0319 (5)	0.0287 (4)	−0.0063 (4)	0.0000 (4)	0.0126 (4)
O2	0.0300 (4)	0.0307 (4)	0.0248 (4)	−0.0032 (3)	0.0037 (3)	0.0110 (3)
C1	0.0221 (5)	0.0215 (5)	0.0199 (5)	0.0024 (4)	0.0080 (4)	0.0084 (4)
C2	0.0253 (5)	0.0207 (5)	0.0206 (5)	0.0059 (4)	0.0113 (4)	0.0073 (4)
C3	0.0210 (5)	0.0220 (5)	0.0203 (5)	0.0063 (4)	0.0105 (4)	0.0096 (4)
C4	0.0205 (5)	0.0206 (5)	0.0186 (5)	0.0048 (4)	0.0094 (4)	0.0082 (4)
C5	0.0213 (5)	0.0210 (5)	0.0211 (5)	0.0056 (4)	0.0111 (4)	0.0092 (4)
C6	0.0192 (5)	0.0236 (5)	0.0239 (5)	0.0049 (4)	0.0103 (4)	0.0099 (4)
C7	0.0229 (5)	0.0248 (5)	0.0207 (5)	0.0025 (4)	0.0071 (4)	0.0067 (4)
C8	0.0216 (5)	0.0218 (5)	0.0194 (5)	0.0044 (4)	0.0080 (4)	0.0030 (4)
C9	0.0213 (5)	0.0193 (5)	0.0245 (5)	0.0056 (4)	0.0114 (4)	0.0085 (4)
C10	0.0263 (5)	0.0320 (6)	0.0233 (5)	0.0104 (4)	0.0127 (4)	0.0121 (5)
C11	0.0318 (6)	0.0373 (6)	0.0308 (6)	0.0144 (5)	0.0204 (5)	0.0142 (5)
C12	0.0251 (5)	0.0343 (6)	0.0358 (6)	0.0136 (5)	0.0173 (5)	0.0166 (5)
C13	0.0239 (5)	0.0321 (6)	0.0272 (6)	0.0099 (4)	0.0099 (4)	0.0132 (5)
C14	0.0260 (5)	0.0272 (5)	0.0234 (5)	0.0090 (4)	0.0129 (4)	0.0100 (4)
C15	0.0192 (5)	0.0203 (5)	0.0212 (5)	0.0072 (4)	0.0075 (4)	0.0067 (4)
C16	0.0229 (5)	0.0239 (5)	0.0271 (5)	0.0064 (4)	0.0112 (4)	0.0076 (4)
C17	0.0228 (5)	0.0243 (5)	0.0396 (7)	0.0050 (4)	0.0121 (5)	0.0076 (5)
C18	0.0236 (5)	0.0259 (6)	0.0331 (6)	0.0069 (5)	0.0034 (5)	−0.0001 (5)
C19	0.0307 (6)	0.0340 (6)	0.0207 (5)	0.0142 (5)	0.0064 (5)	0.0035 (5)
C20	0.0252 (5)	0.0289 (6)	0.0226 (5)	0.0108 (4)	0.0102 (4)	0.0091 (4)
C21	0.0190 (5)	0.0239 (5)	0.0195 (5)	0.0072 (4)	0.0075 (4)	0.0075 (4)
C22	0.0211 (5)	0.0256 (5)	0.0254 (5)	0.0059 (4)	0.0091 (4)	0.0087 (4)
C23	0.0282 (6)	0.0242 (5)	0.0281 (6)	0.0088 (4)	0.0072 (5)	0.0067 (4)
C24	0.0404 (7)	0.0368 (6)	0.0260 (6)	0.0227 (5)	0.0156 (5)	0.0098 (5)
C25	0.0440 (7)	0.0448 (7)	0.0365 (7)	0.0239 (6)	0.0290 (6)	0.0212 (6)
C26	0.0317 (6)	0.0301 (6)	0.0320 (6)	0.0125 (5)	0.0195 (5)	0.0153 (5)
N1	0.0926 (12)	0.0596 (10)	0.0610 (10)	0.0290 (9)	0.0321 (9)	0.0031 (8)
C27	0.0676 (11)	0.0396 (8)	0.0378 (8)	0.0121 (8)	0.0141 (8)	0.0089 (6)
C28	0.0614 (11)	0.0703 (12)	0.0682 (12)	0.0228 (9)	0.0213 (9)	0.0390 (10)

Geometric parameters (Å, º) top

O1—H1	1.01 (2)	C15—C20	1.3928 (15)
O1—C8	1.3022 (13)	C16—H16	0.9500
O2—C8	1.2196 (13)	C16—C17	1.3878 (16)
C1—C2	1.3862 (14)	C17—H17	0.9500
C1—C6	1.3848 (15)	C17—C18	1.3831 (18)
C1—C7	1.5063 (14)	C18—H18	0.9500
C2—H2	0.9500	C18—C19	1.3869 (18)
C2—C3	1.3955 (15)	C19—H19	0.9500
C3—C4	1.4074 (14)	C19—C20	1.3869 (16)
C3—C9	1.4926 (14)	C20—H20	0.9500
C4—C5	1.4091 (13)	C21—C22	1.3938 (15)
C4—C15	1.4906 (14)	C21—C26	1.3956 (15)
C5—C6	1.3959 (14)	C22—H22	0.9500
C5—C21	1.4869 (14)	C22—C23	1.3850 (16)
C6—H6	0.9500	C23—H23	0.9500
C7—H7A	0.9900	C23—C24	1.3823 (17)
C7—H7B	0.9900	C24—H24	0.9500
C7—C8	1.5111 (15)	C24—C25	1.3811 (19)
C9—C10	1.3950 (15)	C25—H25	0.9500
C9—C14	1.3951 (15)	C25—C26	1.3846 (16)
C10—H10	0.9500	C26—H26	0.9500
C10—C11	1.3849 (15)	N1—C27	1.134 (2)
C11—H11	0.9500	C27—C28	1.445 (3)
C11—C12	1.3823 (16)	C28—H28A	0.9800
C12—H12	0.9500	C28—H28B	0.9800
C12—C13	1.3840 (16)	C28—H28C	0.9800
C13—H13	0.9500	C28—H28D	0.9800
C13—C14	1.3873 (15)	C28—H28E	0.9800
C14—H14	0.9500	C28—H28F	0.9800
C15—C16	1.3946 (15)

C8—O1—H1	108.3 (11)	C20—C15—C16	118.67 (10)
C2—C1—C7	120.40 (9)	C15—C16—H16	119.7
C6—C1—C2	118.42 (9)	C17—C16—C15	120.52 (11)
C6—C1—C7	121.11 (9)	C17—C16—H16	119.7
C1—C2—H2	119.1	C16—C17—H17	119.9
C1—C2—C3	121.86 (10)	C18—C17—C16	120.29 (11)
C3—C2—H2	119.1	C18—C17—H17	119.9
C2—C3—C4	119.49 (9)	C17—C18—H18	120.1
C2—C3—C9	116.97 (9)	C17—C18—C19	119.70 (11)
C4—C3—C9	123.51 (9)	C19—C18—H18	120.1
C3—C4—C5	118.89 (9)	C18—C19—H19	120.0
C3—C4—C15	121.46 (9)	C20—C19—C18	120.10 (11)
C5—C4—C15	119.64 (9)	C20—C19—H19	120.0
C4—C5—C21	122.60 (9)	C15—C20—H20	119.6
C6—C5—C4	119.77 (9)	C19—C20—C15	120.72 (11)
C6—C5—C21	117.61 (9)	C19—C20—H20	119.6
C1—C6—C5	121.55 (9)	C22—C21—C5	122.06 (9)
C1—C6—H6	119.2	C22—C21—C26	118.55 (10)
C5—C6—H6	119.2	C26—C21—C5	119.32 (9)
C1—C7—H7A	109.2	C21—C22—H22	119.7
C1—C7—H7B	109.2	C23—C22—C21	120.66 (10)
C1—C7—C8	112.18 (8)	C23—C22—H22	119.7
H7A—C7—H7B	107.9	C22—C23—H23	119.9
C8—C7—H7A	109.2	C24—C23—C22	120.18 (11)
C8—C7—H7B	109.2	C24—C23—H23	119.9
O1—C8—C7	113.30 (9)	C23—C24—H24	120.1
O2—C8—O1	123.66 (10)	C25—C24—C23	119.75 (11)
O2—C8—C7	123.04 (10)	C25—C24—H24	120.1
C10—C9—C3	119.25 (9)	C24—C25—H25	119.8
C10—C9—C14	118.32 (9)	C24—C25—C26	120.38 (11)
C14—C9—C3	122.30 (9)	C26—C25—H25	119.8
C9—C10—H10	119.6	C21—C26—H26	119.8
C11—C10—C9	120.88 (10)	C25—C26—C21	120.47 (11)
C11—C10—H10	119.6	C25—C26—H26	119.8
C10—C11—H11	119.9	N1—C27—C28	179.11 (18)
C12—C11—C10	120.20 (10)	C27—C28—H28A	109.5
C12—C11—H11	119.9	C27—C28—H28B	109.5
C11—C12—H12	120.2	C27—C28—H28C	109.5
C11—C12—C13	119.67 (10)	C27—C28—H28D	109.5
C13—C12—H12	120.2	C27—C28—H28E	109.5
C12—C13—H13	119.9	C27—C28—H28F	109.5
C12—C13—C14	120.29 (10)	H28A—C28—H28B	109.5
C14—C13—H13	119.9	H28A—C28—H28C	109.5
C9—C14—H14	119.7	H28B—C28—H28C	109.5
C13—C14—C9	120.63 (10)	H28D—C28—H28E	109.5
C13—C14—H14	119.7	H28D—C28—H28F	109.5
C16—C15—C4	120.43 (9)	H28E—C28—H28F	109.5
C20—C15—C4	120.89 (9)

C1—C2—C3—C4	−0.81 (14)	C6—C1—C7—C8	−90.31 (11)
C1—C2—C3—C9	177.24 (9)	C6—C5—C21—C22	−121.95 (11)
C1—C7—C8—O1	170.53 (9)	C6—C5—C21—C26	55.02 (13)
C1—C7—C8—O2	−9.46 (15)	C7—C1—C2—C3	−176.72 (9)
C2—C1—C6—C5	0.35 (14)	C7—C1—C6—C5	177.49 (9)
C2—C1—C7—C8	86.78 (12)	C9—C3—C4—C5	−177.54 (9)
C2—C3—C4—C5	0.38 (14)	C9—C3—C4—C15	3.78 (14)
C2—C3—C4—C15	−178.30 (9)	C9—C10—C11—C12	−0.21 (18)
C2—C3—C9—C10	44.96 (13)	C10—C9—C14—C13	−0.39 (16)
C2—C3—C9—C14	−130.96 (11)	C10—C11—C12—C13	−0.72 (18)
C3—C4—C5—C6	0.38 (14)	C11—C12—C13—C14	1.09 (18)
C3—C4—C5—C21	−177.95 (9)	C12—C13—C14—C9	−0.53 (17)
C3—C4—C15—C16	59.69 (13)	C14—C9—C10—C11	0.77 (16)
C3—C4—C15—C20	−121.55 (11)	C15—C4—C5—C6	179.09 (9)
C3—C9—C10—C11	−175.31 (10)	C15—C4—C5—C21	0.76 (14)
C3—C9—C14—C13	175.56 (10)	C15—C16—C17—C18	0.91 (16)
C4—C3—C9—C10	−137.08 (10)	C16—C15—C20—C19	0.27 (15)
C4—C3—C9—C14	47.01 (14)	C16—C17—C18—C19	−0.63 (17)
C4—C5—C6—C1	−0.76 (15)	C17—C18—C19—C20	0.18 (17)
C4—C5—C21—C22	56.41 (14)	C18—C19—C20—C15	0.00 (16)
C4—C5—C21—C26	−126.62 (11)	C20—C15—C16—C17	−0.72 (15)
C4—C15—C16—C17	178.07 (9)	C21—C5—C6—C1	177.65 (9)
C4—C15—C20—C19	−178.51 (10)	C21—C22—C23—C24	0.82 (16)
C5—C4—C15—C16	−118.98 (11)	C22—C21—C26—C25	−0.50 (16)
C5—C4—C15—C20	59.77 (13)	C22—C23—C24—C25	−0.56 (17)
C5—C21—C22—C23	176.70 (10)	C23—C24—C25—C26	−0.23 (19)
C5—C21—C26—C25	−177.58 (10)	C24—C25—C26—C21	0.76 (18)
C6—C1—C2—C3	0.45 (14)	C26—C21—C22—C23	−0.29 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	1.01 (2)	1.62 (2)	2.624 (1)	174 (2)

Symmetry code: (i) −x, −y, −z+1.

Geometric data (Å, °) of short intermolecular interactions top

Cg(A) and Cg(D) refer to the centers of gravity of the rings C1–C6 and C21–C26, respectively

D—H···A/Cg	D—H	H···A/Cg	D···A/Cg	D—H···A/Cg
O1—H1···O2ⁱ	1.01 (2)	1.62 (2)	2.624 (1)	174 (2)
C2—H2···N1ⁱⁱ	0.95	2.71	3.567 (2)	150
C19—H19···O2ⁱⁱⁱ	0.95	2.56	3.477 (1)	163
C7—H7B···Cg(D)^iv	0.99	2.97	3.746 (1)	136
C10—H10···Cg(A)^v	0.95	2.97	3.509 (1)	119

Symmetry codes: (i) -x, -y, -z + 1; (ii) -x + 1, -y, -z + 1; (iii) -x + 1, -y + 1, -z + 2; (iv) -x, -y + 1, -z + 1; (v) -x + 1, -y + 1, -z + 1.

Acknowledgements

We would like to thank the Dr Erich-Krüger-Stiftung for financial support. Open Access Funding by the Publication Fund of the Technische Universität Bergakademie Freiberg is gratefully acknowledged.

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Volume 80| Part 11| November 2024| Pages 1198-1201

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

Crystal structure of an aceto­nitrile solvate of 2-(3,4,5-triphen­ylphen­yl)acetic acid

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure of an acetonitrile solvate of 2-(3,4,5-triphenylphenyl)acetic acid

3. Supramolecular features