Crystal structure and Hirshfeld surface analysis of 4,4′-di­meth­oxy­biphenyl-3,3′,5,5′-tetra­carb­oxy­lic acid dihydrate

Hanauer, T.; Seichter, W.; Mazik, M.

doi:10.1107/S2056989024002305

research communications

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ISSN: 2056-9890

Volume 80| Part 4| April 2024| Pages 413-417

https://doi.org/10.1107/S2056989024002305

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Crystal structure and Hirshfeld surface analysis of 4,4′-dimethoxybiphenyl-3,3′,5,5′-tetracarboxylic acid dihydrate

Thomas Hanauer,^a Wilhelm Seichter ^a and Monika Mazik ^a ^*

^aTechnische Universität Bergakademie Freiberg, Leipziger Str. 29, D-09596 Freiberg/Sachsen, Germany
^*Correspondence e-mail: monika.mazik@chemie.tu-freiberg.de

Edited by J. Ellena, Universidade de Sâo Paulo, Brazil (Received 22 January 2024; accepted 9 March 2024; online 26 March 2024)

In the crystal of the title compound, C₁₈H₁₄O₁₀·2H₂O, the arene rings of the biphenyl moiety are tilted at an angle of 24.3 (1)°, while the planes passing through the carboxyl groups are rotated at angles of 8.6 (1) and 7.7 (1)° out of the plane of the benzene ring to which they are attached. The crystal structure is essentially stabilized by O—H⋯O bonds. Here, the carboxyl groups of neighbouring host molecules are connected by cyclic R₂²(8) synthons, leading to the formation of a three-dimensional network. The water molecules in turn form helical supramolecular strands running in the direction of the crystallographic c-axis (chain-like water clusters). The second H atom of each water molecule provides a link to a methoxy O atom of the host molecule. A Hirshfeld surface analysis was performed to quantify the contributions of the different intermolecular interactions, indicating that the most important contributions to the crystal packing are from H⋯O/O⋯H (37.0%), H⋯H (26.3%), H⋯C/C⋯H (18.5%) and C⋯O/O⋯C (9.5%) interactions.

Keywords: biphenyl derivative; O—H⋯O hydrogen bonds; supramolecular motifs; water cluster; helical supramolecular strands; Hirshfeld surface; crystal structure.

CCDC reference: 2339048

1. Chemical context

Our studies on the molecular recognition of mono- and oligosaccharides with artificial receptors led to the development of various acyclic (Mazik, 2009 , 2012 ) and macrocyclic (Lippe & Mazik, 2013 , 2015 ; Amrhein et al., 2016 ; Amrhein & Mazik, 2021 ; Leibiger et al., 2022 ) receptor architectures. Among the acyclic compounds, those with a central aromatic core carrying three or more functionalized side arms as recognition groups have proven to be effective carbohydrate receptors. Their binding properties can be fine-tuned by varying the structural subunits of these compounds. In this context, benzene (Stapf et al., 2020 ; Köhler et al., 2020 , 2021 ; Kaiser et al., 2019 ), fluorene (Seidel & Mazik, 2020 , 2023 ), diphenylmethane (Mazik & König, 2007 ; Mazik & Buthe, 2009 ; Koch et al., 2014 ) or biphenyl units (Mazik & König, 2006 ) were used as the central aromatic platform of the receptor structures. Representatives of the last mentioned receptors can be prepared, for example, on the basis of biphenyl-3,3′,5,5′-tetracarboxylic acid (Mazik & König, 2006). In this article we describe the crystal structure of the hydrate of 4,4′-dimethoxy-biphenyl-3,3′,5,5′-tetracarboxylic acid, which is also a valuable precursor for the synthesis of receptors with a biphenyl-based scaffold.

2. Structural commentary

The title compound, C₁₈H₁₄O₁₀·2H₂O, crystallizes in the tetragonal space group I4₁cd with one half [the second half is generated by the symmetry operation 1 − x, 1 − y, z] of the biphenyl-4,4′-dimethoxy-3,3′,5,5′-tetracarboxylic acid (host) molecule and one water molecule (guest) in the asymmetric unit of the cell. A perspective view of the 1:2 host–guest unit is shown in Fig. 1. The two benzene rings of the biphenyl moiety are twisted at an angle of 24.3 (1)°. The mean planes passing the carboxy groups are inclined at angles of 8.6 (1) and 7.7 (1)° with respect to the planes of the respective benzene rings. The bond lengths within the host molecule resemble those found in the crystal structure of biphenyl-3,3′,5,5′-tetracarboxylic acid (Coles et al., 2002 ).

Figure 1
Perspective view (ORTEP diagram) including atom labeling of the 1:2 host–guest complex of the title molecule with water. Anisotropic displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features and Hirshfeld surface analysis

The crystal structure is mainly stabilized by O—H⋯O bonds (Table 1). On the one hand, these hydrogen bonds contribute to the connection of the host molecules via cyclic synthons of the structure $[R_{2}^{2}]$ (8) (Etter et al., 1990 ; Etter, 1991 ; Bernstein et al., 1995 ), thus creating a three-dimensional cross-linking of these molecules. On the other hand, the water molecules in turn form infinite helical strands running in the c-axis direction (Fig. 2). The arrangement of the water molecules in this helical structure corresponds to the fourfold symmetry element (4₁ axis) of the crystal structure. The second H atom of the water molecule serves as a binding site for a hydrogen bond to the O atom of the methoxy group (Fig. 3). Taking the interactions between the water molecules into account, their arrangement could also be described as water clusters, which belong to the class of infinite chains (for nomenclature of water clusters, see: Infantes & Motherwell, 2002 ; Mascal et al., 2006 ; for examples of other water clusters reported by our group, see: Rosin et al., 2017 ). Furthermore, the H⋯Cg distances of 2.96 and 2.99 Å involving the hydrogen atoms H3 and H5 (symmetry operations: x, 1 − y, $[{1\over 2}]$ + z; 1 − x, y, − $[{1\over 2}]$ + z) indicate the presence of weak C—H⋯π interactions. A packing diagram of the title compound viewed along the c-axis direction is presented in Fig. 4.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O5ⁱ	0.88 (6)	1.80 (6)	2.663 (4)	166 (7)
O4—H1O4⋯O1ⁱⁱ	0.88 (3)	1.74 (3)	2.611 (4)	174 (7)
O6—H1O6⋯O6ⁱⁱⁱ	0.91 (3)	1.86 (3)	2.768 (4)	173 (5)
O6—H2O6⋯O3	0.90 (3)	2.04 (3)	2.941 (5)	174 (7)
Symmetry codes: (i) $[-y+1, -x+{\script{1\over 2}}, z-{\script{1\over 4}}]$ ; (ii) $[-y+{\script{1\over 2}}, -x+1, z+{\script{1\over 4}}]$ ; (iii) $[y, -x+{\script{1\over 2}}, z+{\script{1\over 4}}]$ .

Figure 2
Part of the crystal structure of the title compound showing the helical strands of O—H⋯O-bonded water molecules running along the c-axis direction. Dashed lines represent hydrogen-bond interactions.

Figure 3
Part of the crystal structure of the title compound showing the mode of hydrogen bonding.

Figure 4
Packing diagram of the title compound viewed down the crystallographic c-axis. Dashed lines represent hydrogen-bond interactions.

In order to visualize and quantify intermolecular interactions a Hirshfeld surface analysis (Spackman & Byrom, 1997 ; McKinnon et al., 1998 ) was performed using CrystalExplorer (Version 21.5, Spackman et al., 2021 ). The Hirshfeld surface mapped over d_norm using a standard surface resolution with a fixed colour scale of −0.7603 to 1.5689 a.u. is shown in Fig. 5. The red spots on the d_norm surface represent O—H⋯O hydrogen bonds. The full two-dimensional fingerprint plots and those delineated into different types of interactions (McKinnon, 2007 ) are illustrated in Fig. 6. They reveal that H⋯O/O⋯H contacts (Fig. 6b), i.e. strong hydrogen bonds, contribute 37.0% of the Hirshfeld surface. The two weakly pronounced wings in the fingerprint plot prove the presence of intermolecular interactions of the C—H⋯π type. H⋯H contacts represent 26.3% of the fingerprint plot, while H⋯C/C⋯H and C⋯O/O⋯C contacts cover 18.5% and 9.5% of the Hirshfeld surface, respectively.

Figure 5
View of the three-dimensional Hirshfeld surface of the title compound, plotted over d_norm in the range −0.7606 to 1.5689 a.u., generated with CrystalExplorer (Spackman et al., 2021

)

Figure 6
Two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) H⋯O/O⋯H, (c) H⋯C/C⋯H, (d) C⋯O/O⋯C, (e) O⋯O, (f) C⋯C and (g) H⋯H interactions. The d_i and d_e values represent the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

4. Database survey

A search in the Cambridge Structural Database (CSD, Version 5.44, update April 2023; Groom et al., 2016 ) for 4,4′-disubstituted derivatives of biphenyl-3,3′,5,5′-tetracarboxylic acid gave no hits; however, the crystal structure of biphenyl-3,3′,5,5′-tetracarboxylic acid is known (refcode: PUYTEI; Coles et al., 2002). A comparison between the structure of the title compound and the unsolvated structure of biphenyl-3,3′,5,5′-tetracarboxylic acid (PUYTEI) provides a hint about the influence of the water molecules on the packing of the crystal structure. The difference in the space-group symmetries (I4₁cd vs P2₁/c) suggests structural differences. In the structure of PUYTEI, a supramolecular arrangement of three interpenetrating corrugated layers forms structure domains that extend parallel to the crystallographic ac plane. Within a given corrugated layer, adjacent molecules are also linked via their carboxyl groups through eight-membered ring synthons. Furthermore, the molecules within the structure domains are arranged such that offset π–π-stacking interactions [d(Cg⋯Cg) = 3.636 Å] are effective between their aromatic units.

5. Synthesis and crystallization

To a mixture of 760 mg (1.51 mmol) of 4,4′-dimethoxy-3,3′,5,5′-biphenyltetracarboxylic acid tetraethyl ester and 60 mL of water, 1.01 g (17.9 mmol) of potassium hydroxide were added. After heating to boiling point for up to 18 h, the solution was cooled and acidified with semi-concentrated sulfuric acid. The white solid was filtered and dried under reduced pressure. Yield 96% (578 mg, 1.48 mmol); m.p. 528 K. ¹H NMR (500 MHz, DMSO-d₆, ppm): δ = 3.85 (s, 6H), 8.08 (s, 4H), 13.31 (br. s, 4H). ¹³C NMR (125 MHz, DMSO-d₆, ppm): δ = 63.0, 128.4, 131.0, 133.1, 157.1, 166.7. Single crystals suitable for X-ray analysis were obtained by recrystallizing the resulting solid from water.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The non-hydrogen atoms were refined anisotropically. The carboxyl H atoms and the hydrogen atoms of the water molecules were identified in difference-Fourier maps and their U_iso parameters refined freely. All other H atoms were placed in calculated positions and refined using a riding model with C—H = 0.95–0.98 Å and U_iso(H) = 1.2 or 1.5 U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₄O₁₀·2H₂O
M_r	426.32
Crystal system, space group	Tetragonal, I4₁cd
Temperature (K)	123
a, c (Å)	24.069 (3), 6.4468 (8)
V (Å³)	3734.6 (9)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.13
Crystal size (mm)	0.40 × 0.03 × 0.03

Data collection
Diffractometer	Stoe IPDS 2T
No. of measured, independent and observed [I > 2σ(I)] reflections	14573, 1914, 1502
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.093, 1.08
No. of reflections	1914
No. of parameters	153
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.20
Absolute structure	Flack x determined using 575 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	−2.2 (10)
Computer programs: X-AREA and X-RED (Stoe & Cie, 2002 ), SHELXT2018/2 (Sheldrick, 2015 a), SHELXL2018/3 (Sheldrick, 2015 b), XP in SHELXTL (Sheldrick, 2008 ), WinGX (Farrugia, 2012 ), publCIF (Westrip, 2010 ) and ShelXle (Hübschle et al., 2011 ).

Supporting information

CCDC reference: 2339048

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989024002305/ex2080sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024002305/ex2080Isup2.hkl

checkCIF report

Computing details top

4,4'-Dimethoxybiphenyl-3,3',5,5'-tetracarboxylic acid dihydrate top

Crystal data top

C₁₈H₁₄O₁₀·2H₂O	D_x = 1.516 Mg m⁻³
M_r = 426.32	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁cd	Cell parameters from 1164 reflections
a = 24.069 (3) Å	θ = 3.7–23.3°
c = 6.4468 (8) Å	µ = 0.13 mm⁻¹
V = 3734.6 (9) Å³	T = 123 K
Z = 8	Needle, colorless
F(000) = 1776	0.40 × 0.03 × 0.03 mm

Data collection top

Stoe IPDS 2T diffractometer	1502 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	R_int = 0.055
Plane graphite monochromator	θ_max = 26.5°, θ_min = 2.7°
Detector resolution: 6.67 pixels mm^-1	h = −30→30
rotation method scans	k = −30→30
14573 measured reflections	l = −7→8
1914 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.0377P)² + 2.9912P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.093	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.22 e Å⁻³
1914 reflections	Δρ_min = −0.20 e Å⁻³
153 parameters	Absolute structure: Flack x determined using 575 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
4 restraints	Absolute structure parameter: −2.2 (10)

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
O1	0.51833 (11)	0.31455 (13)	0.2339 (6)	0.0237 (8)
O2	0.42995 (12)	0.28601 (12)	0.2186 (6)	0.0239 (8)
H1O2	0.449 (3)	0.256 (3)	0.185 (12)	0.05 (2)*
O3	0.35137 (11)	0.35799 (11)	0.3165 (6)	0.0179 (5)
O4	0.28338 (12)	0.43760 (11)	0.4265 (6)	0.0248 (8)
H1O4	0.2495 (15)	0.450 (3)	0.443 (13)	0.07 (2)*
O5	0.31378 (12)	0.52496 (11)	0.4093 (6)	0.0222 (7)
C1	0.39269 (17)	0.39659 (18)	0.3264 (9)	0.0140 (6)
C2	0.37996 (17)	0.45289 (16)	0.3673 (7)	0.0140 (9)
C3	0.42244 (16)	0.49250 (17)	0.3661 (6)	0.0127 (9)
H3	0.413302	0.530267	0.392110	0.015*
C4	0.47773 (17)	0.47854 (17)	0.3282 (9)	0.0124 (5)
C5	0.48953 (17)	0.42264 (17)	0.2878 (7)	0.0137 (9)
H5	0.526771	0.412055	0.259073	0.016*
C6	0.44816 (17)	0.38202 (16)	0.2884 (7)	0.0142 (9)
C7	0.46785 (15)	0.32382 (17)	0.2435 (7)	0.0156 (9)
C8	0.33949 (17)	0.32976 (16)	0.5113 (7)	0.0271 (9)
H8A	0.308463	0.303926	0.491492	0.041*
H8B	0.329565	0.357244	0.617154	0.041*
H8C	0.372435	0.309100	0.556346	0.041*
C9	0.32219 (16)	0.47463 (15)	0.4027 (8)	0.0155 (9)
O6	0.30431 (14)	0.28767 (14)	−0.0127 (6)	0.0401 (8)
H1O6	0.302 (2)	0.2570 (16)	0.070 (7)	0.042 (15)*
H2O6	0.321 (3)	0.309 (3)	0.084 (9)	0.09 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0149 (13)	0.0148 (15)	0.041 (2)	0.0036 (10)	0.0022 (14)	−0.0036 (15)
O2	0.0179 (13)	0.0110 (15)	0.043 (2)	−0.0020 (11)	0.0022 (14)	−0.0074 (15)
O3	0.0136 (13)	0.0131 (13)	0.0270 (12)	−0.0032 (9)	0.0003 (12)	−0.0021 (12)
O4	0.0101 (14)	0.0168 (14)	0.047 (2)	0.0004 (10)	0.0038 (15)	−0.0043 (14)
O5	0.0126 (13)	0.0170 (13)	0.037 (2)	0.0036 (10)	0.0038 (15)	−0.0010 (14)
C1	0.0113 (19)	0.0159 (19)	0.0146 (14)	−0.0022 (11)	−0.0012 (17)	0.0004 (17)
C2	0.0126 (19)	0.0133 (18)	0.016 (2)	0.0019 (15)	−0.0009 (17)	−0.0020 (17)
C3	0.0131 (17)	0.0119 (18)	0.013 (2)	−0.0007 (14)	−0.0030 (18)	−0.0004 (17)
C4	0.0117 (19)	0.0137 (19)	0.0118 (14)	0.0007 (10)	−0.0030 (16)	−0.0001 (17)
C5	0.0093 (17)	0.0163 (19)	0.016 (2)	0.0034 (14)	−0.0002 (17)	−0.0001 (19)
C6	0.019 (2)	0.0106 (19)	0.014 (2)	−0.0002 (15)	0.0004 (18)	−0.0002 (17)
C7	0.0157 (17)	0.0125 (19)	0.019 (2)	−0.0012 (15)	0.0031 (19)	0.0006 (17)
C8	0.022 (2)	0.024 (2)	0.035 (2)	−0.0026 (16)	0.0039 (18)	0.0104 (18)
C9	0.0138 (19)	0.0166 (18)	0.016 (2)	0.0024 (15)	−0.0012 (18)	0.0016 (17)
O6	0.045 (2)	0.0366 (18)	0.039 (2)	−0.0051 (15)	−0.0063 (16)	−0.0029 (16)

Geometric parameters (Å, º) top

O1—C7	1.237 (4)	C3—C4	1.394 (6)
O2—C7	1.298 (5)	C3—H3	0.9500
O2—H1O2	0.88 (6)	C4—C5	1.400 (6)
O3—C1	1.363 (4)	C4—C4ⁱ	1.489 (6)
O3—C8	1.456 (5)	C5—C6	1.396 (6)
O4—C9	1.300 (5)	C5—H5	0.9500
O4—H1O4	0.88 (3)	C6—C7	1.507 (6)
O5—C9	1.229 (4)	C8—H8A	0.9800
C1—C6	1.402 (6)	C8—H8B	0.9800
C1—C2	1.414 (6)	C8—H8C	0.9800
C2—C3	1.398 (6)	O6—H1O6	0.91 (3)
C2—C9	1.503 (6)	O6—H2O6	0.90 (3)

C7—O2—H1O2	105 (4)	C4—C5—H5	119.1
C1—O3—C8	114.9 (4)	C5—C6—C1	120.3 (4)
C9—O4—H1O4	117 (5)	C5—C6—C7	115.2 (4)
O3—C1—C6	121.1 (4)	C1—C6—C7	124.5 (3)
O3—C1—C2	120.3 (4)	O1—C7—O2	123.9 (4)
C6—C1—C2	118.6 (2)	O1—C7—C6	119.1 (4)
C3—C2—C1	119.6 (4)	O2—C7—C6	117.0 (3)
C3—C2—C9	116.1 (3)	O3—C8—H8A	109.5
C1—C2—C9	124.2 (3)	O3—C8—H8B	109.5
C4—C3—C2	122.3 (4)	H8A—C8—H8B	109.5
C4—C3—H3	118.8	O3—C8—H8C	109.5
C2—C3—H3	118.8	H8A—C8—H8C	109.5
C3—C4—C5	117.3 (2)	H8B—C8—H8C	109.5
C3—C4—C4ⁱ	121.3 (5)	O5—C9—O4	123.6 (4)
C5—C4—C4ⁱ	121.4 (5)	O5—C9—C2	120.1 (4)
C6—C5—C4	121.9 (4)	O4—C9—C2	116.4 (3)
C6—C5—H5	119.1	H1O6—O6—H2O6	95 (6)

C8—O3—C1—C6	90.3 (6)	C4—C5—C6—C7	−179.6 (5)
C8—O3—C1—C2	−92.3 (6)	O3—C1—C6—C5	176.4 (4)
O3—C1—C2—C3	−176.6 (5)	C2—C1—C6—C5	−1.1 (9)
C6—C1—C2—C3	0.9 (9)	O3—C1—C6—C7	−2.7 (8)
O3—C1—C2—C9	0.1 (8)	C2—C1—C6—C7	179.8 (4)
C6—C1—C2—C9	177.6 (4)	C5—C6—C7—O1	8.4 (7)
C1—C2—C3—C4	−0.8 (8)	C1—C6—C7—O1	−172.4 (5)
C9—C2—C3—C4	−177.8 (4)	C5—C6—C7—O2	−172.1 (4)
C2—C3—C4—C5	0.9 (8)	C1—C6—C7—O2	7.1 (7)
C2—C3—C4—C4ⁱ	−179.9 (3)	C3—C2—C9—O5	6.7 (7)
C3—C4—C5—C6	−1.1 (8)	C1—C2—C9—O5	−170.1 (5)
C4ⁱ—C4—C5—C6	179.7 (3)	C3—C2—C9—O4	−172.8 (4)
C4—C5—C6—C1	1.2 (8)	C1—C2—C9—O4	10.4 (7)

Symmetry code: (i) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O5ⁱⁱ	0.88 (6)	1.80 (6)	2.663 (4)	166 (7)
O4—H1O4···O1ⁱⁱⁱ	0.88 (3)	1.74 (3)	2.611 (4)	174 (7)
O6—H1O6···O6^iv	0.91 (3)	1.86 (3)	2.768 (4)	173 (5)
O6—H2O6···O3	0.90 (3)	2.04 (3)	2.941 (5)	174 (7)

Symmetry codes: (ii) −y+1, −x+1/2, z−1/4; (iii) −y+1/2, −x+1, z+1/4; (iv) y, −x+1/2, z+1/4.

Acknowledgements

TH would like to thank the Free State of Saxony for funding (Saxon State Doctoral Scholarship). Open Access Funding by the Publication Fund of the Technische Universität Bergakademie Freiberg is gratefully acknowledged.

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