Syntheses and structures of two anthracene–benzoic acid derivatives as potential MOF linkers

Kushwaha, S.; Thapliyal, A.; Mishra, A.K.; Singh, U.P.; Butcher, R.J.

doi:10.1107/S2056989025008503

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ISSN: 2056-9890

Volume 81| Part 11| November 2025| Pages 1063-1066

https://doi.org/10.1107/S2056989025008503

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Syntheses and structures of two anthracene–benzoic acid derivatives as potential MOF linkers

Shagun Kushwaha,^a Amit Thapliyal,^a Anil K. Mishra,^a Udai P. Singh ^a ^* and Ray J. Butcher ^b

^aDepartment of Chemistry, Indian Institute of Technology Roorkee, Roorkee - 247667, India, and ^bDepartment of Chemistry, Howard University, 525 College St NW, Washington DC 20059, USA
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 7 July 2025; accepted 27 September 2025; online 28 October 2025)

In the title compounds, 2,2′-{[anthracene-9,10-diylbis(methylene)]bis(sulfanediyl)}dibenzoic acid dimethylacetamide tetrasolvate, C₃₀H₂₂O₄S₂·4C₄H₉NO 1 and 4,4′-{[anthracene-9,10-diylbis(methylene)]bis(oxy)}dibenzoic acid dimethylformamide disolvate, C₃₀H₂₂O₆·2C₃H₇NO 2, the complete anthracene–benzoic acid molecule is generated by a crystallographic centre of symmetry. The dihedral angle between the anthracene ring system and the pendant ring is 71.43 (7) in 1 and 75.27 (12)° in 2. In the extended structures of 1 and 2, O—H⋯O hydrogen bonds link the main molecules into pairs of solvent molecules to generate trimers. Weak C—H⋯O and C—H⋯π interactions further consolidate both structures.

Keywords: crystal structure; anthracene derivatized ligands.

CCDC references: 2491864; 2491863

1. Chemical context

Anthracene is a rigid and planar tricyclic aromatic hydrocarbon, has extensive π-conjugation, high photoluminescence efficiency and good thermal stability (Klosterman et al., 2009 ; Hunter et al., 2001 ). The anthracene core serves as a light-harvesting chromophore and a versatile structural unit for designing functional materials such as organic semiconductors, photoresponsive switches, fluorescent sensors and supramolecular hosts (Desiraju & Gavezzotti, 1989 ). In coordination chemistry, the incorporation of anthracene into ligands can significantly influence both the structural and electronic characteristics of the resulting complexes as reported by our group (e.g., Verma et al., 2022 ) and others (e.g., Jindal et al., 2021 ).

Herein we report the syntheses and crystal structures of the title compounds, 1 and 2, with a thioether and ether linkage between the anthracene ring system and benzoic acid moiety, respectively. These compounds could act as potential linkers in metal–organic frameworks (MOFs) after deprotonation of the carboxylic acid.

2. Structural commentary

Compound 1 (Fig. 1) crystallizes in the monoclinic space group P2₁/c with half of the main molecule and two dimethylacetamide (DMA) solvent molecules in the asymmetric unit. The dihedral angle between the anthracene ring system and the phenyl ring of the 2-mercaptobenzoic acid moiety is 71.43 (7)°. The torsion angle between the anthracene ring and phenyl group (C1—C8—S1—C9) is 178.13 (9)° indicating an anti conformation for this grouping and the C8—S1—C9 bond angle is 103.13 (7)°. Compound 2 (Fig. 2) crystallizes in space group P2₁/n with half of the main molecule and one dimethylformamide (DMF) molecule in the asymmetric unit. The C8—O1—C9 bond angle is 117.8 (2)° and the C1—C8—O1—C9 torsion angle is −178.3 (2)°, indicating an anti conformation. The dihedral angle between the plane of anthracene ring system and the phenyl ring of the 4-hydroxybenzoic acid moiety is 75.27 (12)°.

Figure 1
The molecular structure of 1 showing displacement ellipsoids drawn at the 50% level. Symmetry code: 1 − x, 1 − y, 1 − z.

Figure 2
The molecular structure of 2 showing displacement ellipsoids drawn at the 50% level. Symmetry code: 1 − x, −y, −z.

3. Supramolecular features

In the extended structure of 1, the carboxylic acid group of the ligand forms an O2—H2⋯O3A hydrogen bond with the DMA molecule with an H⋯O bond length of 1.94 Å. The structure of 1 is further consolidated by a number of C—H⋯O, C—H⋯S and C—H⋯π weak interactions (Table 1). Among these, consecutive C—H⋯π interactions occur between the C4—H4 group of the anthracene ring and the centroid (Cg1) of the adjacent benzene ring with an H⋯π separation of 2.76 Å (Fig. 3). The packing also features a weak hydrogen bond between the methylene hydrogen atoms of the anthracene ring and oxygen atom of DMF molecule (C8—H8B⋯O4A) at a distance of 2.48 Å, forming infinite chains running parallel to each other.

Table 1
Hydrogen-bond geometry (Å, °) for 1

Cg1 is the centroid of the C9–C14 ring of 1.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3Aⁱ	0.84	1.94	2.770 (14)	169
C8—H8B⋯O4Aⁱⁱ	0.99	2.48	3.126 (8)	122
C17—H17A⋯O4ⁱⁱⁱ	0.98	2.62	3.518 (8)	152
C18A—H18D⋯S1ⁱⁱⁱ	0.98	3.02	3.83 (3)	142
C19A—H19E⋯O4Aⁱⁱⁱ	0.98	2.43	3.40 (4)	168
C21—H21C⋯O1	0.98	2.49	3.422 (7)	158
C22A—H22F⋯O1	0.98	2.54	3.51 (3)	168
C4—H4⋯Cg1	0.95	2.76	3.49	135
Symmetry codes: (i) ; (ii) ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 3
The packing of 1 showing C—H⋯π interactions.

A similar strong hydrogen bond occurs in 2, between the carboxylic acid group of the ligand and oxygen atom of the DMF molecule (O3—H3⋯O4) at a distance of 1.74 Å and the packing is supported by various weak interactions (Table 2), including consecutive C—H⋯π interactions involving the aromatic C11—H11 group of the phenyl ring and the centroid (Cg2) of the adjacent anthracene ring at an H⋯π distance of 3.07 Å, resulting in an array of chains running parallel to each other (Fig. 4). Additionally, the packing of 2 is reinforced by the hydrogen-bond interactions between the aromatic H atom of the benzene ring of one molecule and the oxygen atom of the ether bond in the adjacent molecule (C10—H10⋯O1) at a distance of 2.67 Å.

Table 2
Hydrogen-bond geometry (Å, °) for 2

Cg2 is the centroid of the C9–C14 ring of 2.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.84	1.74	2.575 (3)	175
C8—H8A⋯O2ⁱ	0.99	2.54	3.429 (4)	149
C16—H16⋯O2	0.95	2.31	3.080 (4)	138
C4—H4⋯Cg2	0.95	3.07	3.96	157
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 4
The packing of 2 showing C—H⋯π interactions.

4. Database survey

A simple name search in the Cambridge Structural Database (CSD version 5.46, November 2024; Groom et al., 2016 ) of both compounds 1 and 2 resulted in no hits. However, searching for the fragment anthracene-9,10-diylbis(methylene) resulted in more than thirty similar structures, for example including CSD refcode BIHNIR (Suresh et al., 2013 ), XUTHAZ (Verma et al., 2025 ), TAPYEQ (Chen et al., 2010 ), WUTGUO01 (Kan et al., 2011 ), YIGCEA (Li et al., 2023 ) and ZIHFEF (Verma et al., 2023 ). These structures are either ligand molecules or metal-organic structures having different substituents on the anthracene-9,10-diylbis(methylene) moiety.

5. Synthesis and crystallization

As outlined in Figs. 5 and 6, 2-mercaptobenzoic acid (2.0 mmol) and potassium carbonate (4.0 mmol) were dissolved in an acetone:water (1:1) mixture and refluxed for 1 h. After an hour, 9,10-bis(bromomethyl)anthracene (1.0 mmol) was added to the reaction mixture and it was refluxed overnight. After the completion of reaction, mixture was neutralized with 1 N HCl solution and the yellow precipitate was filtered, washed with water and dried to yield a yellow solid (yield: 92%). ¹H-NMR (500MHz, DMSO-d₆): δ 5.17 (s, 4H), 7.27–7.31 (m, 2H), 7.58–7.60 (m, 4H), 7.64–7.67 (m, 2H), 7.90–7.93 (m, 4H), 8.37–8.39 (m, 4H), 13.05 (s, 2H). The crystals of 1 were obtained by a solvothermal method using DMA solvent at 363 K for 96 h.

Figure 5
Synthesis schemes for compound 1.

Figure 6
Synthesis schemes for compound 2.

To prepare 2, methyl-4-hydroxybenzoate was synthesized by following the previously reported procedure (Mondal et al., 2023 ). Methyl-4-hydroxybenzoate (2.0 mmol) and potassium carbonate (2.2 mmol) were dissolved in acetonitrile (20 ml) and refluxed for 1 h. After an hour, 9,10-bis(bromomethyl)anthracene (1.0 mmol) was added to the reaction mixture and refluxed overnight. After the completion of reaction, it was neutralized with 1 N HCl solution and the solid product was filtered, washed with water and dried in a hot air oven (yield: 92%). ¹H-NMR (500MHz, DMSO-d₆): δ 3.81 (s, 6H), 6.17 (s, 4H), 7.27–7.29 (d, 4H), 7.59–7.61 (m, 4H), 7.95–7.96 (d, 4H), 8.39–8.41 (m, 4H). The methyl ester derivative was taken in a 100 ml round-bottom flask and dissolved in mixed solvents of THF:MeOH (1:1). 4 M NaOH was added into the reaction mixture and stirred for 24 h at RT. After the completion of reaction, it was neutralized with 1 N HCl solution and precipitate was filtered, washed with water and dried (yield: 85%). Crystals of 2 were obtained by a solvothermal method using DMF solvent at 373 K for 72 h.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The H atoms attached to carbon atoms were refined using a riding model with U_iso(H) = 1.2U_eq(C). In 1, both DMA molecules were found to be disordered in a similar manner. This was modeled using SAME instructions in SHELXL for each component and resulted in occupancies of 0.799 (3)/0.201 (3) and 0.804 (3)/0.196 (3), respectively.

Table 3
Experimental details

	1	2
Crystal data
Chemical formula	C₃₀H₂₂O₄S₂·4C₄H₉NO	C₃₀H₂₂O₆·2C₃H₇NO
M_r	859.08	624.67
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/n
Temperature (K)	104	104
a, b, c (Å)	9.9818 (3), 9.2026 (2), 24.1998 (7)	10.8761 (10), 9.6711 (9), 14.8968 (14)
β (°)	91.016 (1)	100.519 (3)
V (Å³)	2222.61 (10)	1540.6 (2)
Z	2	2
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.18	0.10
Crystal size (mm)	0.35 × 0.15 × 0.12	0.26 × 0.19 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD	Bruker APEXII CCD
Absorption correction	Multi-scan (OLEX2; Dolomanov et al., 2009 )	Multi-scan (OLEX2; Dolomanov et al., 2009)
T_min, T_max	0.706, 0.746	0.666, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	84923, 5544, 4374	49734, 3169, 1669
R_int	0.076	0.179
(sin θ/λ)_max (Å⁻¹)	0.668	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.112, 1.03	0.069, 0.182, 1.02
No. of reflections	5544	3169
No. of parameters	394	211
No. of restraints	422	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.27	0.31, −0.24
Computer programs: APEX4, APEX2 and SAINT (Bruker, 2016 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL-2019/2 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009).

Supporting information

CCDC references: 2491864; 2491863

Crystal structure: contains datablocks 1, 2. DOI: https://doi.org/10.1107/S2056989025008503/hb8146sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989025008503/hb81461sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989025008503/hb81462sup3.hkl

checkCIF report

Computing details top

2,2'-{[Anthracene-9,10-diylbis(methylene)]bis(sulfanediyl)}dibenzoic acid dimethylacetamide tetrasolvate (1) top

Crystal data top

C₃₀H₂₂O₄S₂·4C₄H₉NO	F(000) = 916
M_r = 859.08	D_x = 1.284 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.9818 (3) Å	Cell parameters from 9910 reflections
b = 9.2026 (2) Å	θ = 2.4–25.7°
c = 24.1998 (7) Å	µ = 0.18 mm⁻¹
β = 91.016 (1)°	T = 104 K
V = 2222.61 (10) Å³	Block, clear yellowish yellow
Z = 2	0.35 × 0.15 × 0.12 mm

Data collection top

Bruker APEXII CCD diffractometer	4374 reflections with I > 2σ(I)
ω and φ scans	R_int = 0.076
Absorption correction: multi-scan (Olex2; Dolomanov et al., 2009)	θ_max = 28.3°, θ_min = 1.7°
T_min = 0.706, T_max = 0.746	h = −13→13
84923 measured reflections	k = −12→12
5544 independent reflections	l = −32→32

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0474P)² + 1.119P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5544 reflections	Δρ_max = 0.41 e Å⁻³
394 parameters	Δρ_min = −0.27 e Å⁻³
422 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)
S1	0.49737 (4)	0.76829 (4)	0.38089 (2)	0.01827 (10)
O1	0.29231 (11)	0.87413 (12)	0.31863 (4)	0.0263 (3)
O2	0.31257 (12)	0.96903 (14)	0.23437 (5)	0.0310 (3)
H2	0.230729	0.948146	0.232140	0.047*
C1	0.56861 (14)	0.58987 (15)	0.46196 (6)	0.0167 (3)
C2	0.52491 (14)	0.45046 (15)	0.44587 (6)	0.0173 (3)
C3	0.54843 (16)	0.39496 (16)	0.39171 (6)	0.0224 (3)
H3	0.593487	0.454054	0.365752	0.027*
C4	0.50773 (17)	0.25944 (17)	0.37653 (6)	0.0267 (4)
H4	0.525167	0.224961	0.340360	0.032*
C5	0.43976 (17)	0.16965 (17)	0.41413 (7)	0.0273 (4)
H5	0.411335	0.075326	0.403109	0.033*
C6	0.41483 (16)	0.21774 (16)	0.46609 (6)	0.0228 (3)
H6	0.369268	0.155798	0.490923	0.027*
C7	0.54455 (14)	0.64077 (15)	0.51567 (6)	0.0171 (3)
C8	0.63542 (15)	0.68688 (16)	0.42042 (6)	0.0192 (3)
H8A	0.694092	0.629672	0.396056	0.023*
H8B	0.689817	0.762652	0.439262	0.023*
C9	0.57997 (15)	0.88537 (15)	0.33438 (6)	0.0177 (3)
C10	0.71660 (16)	0.91600 (16)	0.34057 (6)	0.0217 (3)
H10	0.766922	0.871749	0.369702	0.026*
C11	0.77937 (17)	1.01029 (17)	0.30463 (7)	0.0251 (3)
H11	0.871972	1.031090	0.309790	0.030*
C12	0.70906 (17)	1.07443 (16)	0.26140 (6)	0.0247 (3)
H12	0.752673	1.139489	0.237117	0.030*
C13	0.57494 (16)	1.04298 (16)	0.25390 (6)	0.0223 (3)
H13	0.526989	1.085006	0.223637	0.027*
C14	0.50800 (15)	0.95009 (15)	0.29011 (6)	0.0195 (3)
C15	0.36146 (16)	0.92700 (16)	0.28293 (6)	0.0211 (3)
O3	1.0671 (4)	0.9058 (3)	0.2180 (2)	0.0353 (7)	0.799 (3)
N1	0.88738 (18)	0.9245 (2)	0.16135 (7)	0.0285 (5)	0.799 (3)
C16	0.9981 (2)	0.9800 (2)	0.18493 (9)	0.0274 (5)	0.799 (3)
C17	1.0361 (8)	1.1340 (7)	0.1719 (4)	0.0353 (10)	0.799 (3)
H17A	1.050112	1.143580	0.132038	0.053*	0.799 (3)
H17B	1.118931	1.159241	0.191974	0.053*	0.799 (3)
H17C	0.964103	1.199522	0.183008	0.053*	0.799 (3)
C18	0.8425 (6)	0.7782 (5)	0.1765 (3)	0.0369 (10)	0.799 (3)
H18A	0.816616	0.724555	0.142961	0.055*	0.799 (3)
H18B	0.765414	0.785502	0.200811	0.055*	0.799 (3)
H18C	0.915606	0.726820	0.195702	0.055*	0.799 (3)
C19	0.7988 (6)	1.0049 (7)	0.1234 (3)	0.0360 (11)	0.799 (3)
H19A	0.781855	0.946712	0.090114	0.054*	0.799 (3)
H19B	0.841408	1.096737	0.113248	0.054*	0.799 (3)
H19C	0.713733	1.024955	0.141564	0.054*	0.799 (3)
O3A	1.0538 (16)	0.8659 (15)	0.2192 (8)	0.036 (2)	0.201 (3)
N1A	0.9312 (8)	1.0021 (9)	0.1604 (3)	0.0294 (12)	0.201 (3)
C16A	0.9542 (8)	0.8815 (9)	0.1884 (3)	0.0296 (12)	0.201 (3)
C17A	0.858 (2)	0.757 (2)	0.1825 (13)	0.035 (3)	0.201 (3)
H17D	0.766243	0.793275	0.184933	0.052*	0.201 (3)
H17E	0.875504	0.686684	0.212185	0.052*	0.201 (3)
H17F	0.870396	0.709975	0.146647	0.052*	0.201 (3)
C18A	0.815 (2)	1.025 (3)	0.1230 (13)	0.034 (3)	0.201 (3)
H18D	0.767338	1.113996	0.133881	0.051*	0.201 (3)
H18E	0.753673	0.942141	0.125383	0.051*	0.201 (3)
H18F	0.845163	1.035463	0.084941	0.051*	0.201 (3)
C19A	1.022 (3)	1.128 (3)	0.1644 (16)	0.033 (3)	0.201 (3)
H19D	0.983823	1.201294	0.188723	0.050*	0.201 (3)
H19E	1.034642	1.169307	0.127565	0.050*	0.201 (3)
H19F	1.109197	1.096129	0.179621	0.050*	0.201 (3)
O4	−0.0836 (2)	0.7997 (3)	0.45732 (9)	0.0501 (6)	0.804 (3)
N2	0.1140 (2)	0.7946 (2)	0.50291 (9)	0.0326 (5)	0.804 (3)
C20	0.0317 (2)	0.8450 (2)	0.46303 (9)	0.0317 (5)	0.804 (3)
C21	0.0868 (7)	0.9608 (6)	0.4254 (2)	0.0367 (8)	0.804 (3)
H21A	0.123902	1.040534	0.447754	0.055*	0.804 (3)
H21B	0.014736	0.997995	0.401298	0.055*	0.804 (3)
H21C	0.157583	0.918999	0.402787	0.055*	0.804 (3)
C22	0.0711 (7)	0.6745 (7)	0.53909 (16)	0.0553 (13)	0.804 (3)
H22A	0.083561	0.703059	0.577852	0.083*	0.804 (3)
H22B	0.125009	0.587919	0.531637	0.083*	0.804 (3)
H22C	−0.023695	0.652905	0.531759	0.083*	0.804 (3)
C23	0.2478 (4)	0.8572 (5)	0.51334 (18)	0.0365 (9)	0.804 (3)
H23A	0.300280	0.791520	0.537132	0.055*	0.804 (3)
H23B	0.238720	0.951551	0.531667	0.055*	0.804 (3)
H23C	0.293469	0.870156	0.478167	0.055*	0.804 (3)
O4A	−0.0743 (8)	0.7207 (12)	0.4693 (4)	0.0496 (19)	0.196 (3)
N2A	0.1243 (8)	0.8380 (9)	0.4771 (4)	0.0332 (12)	0.196 (3)
C20A	0.0371 (9)	0.7362 (11)	0.4923 (4)	0.0369 (12)	0.196 (3)
C21A	0.064 (3)	0.694 (3)	0.5513 (6)	0.039 (2)	0.196 (3)
H21D	0.129391	0.761244	0.567808	0.059*	0.196 (3)
H21E	0.099197	0.594970	0.552752	0.059*	0.196 (3)
H21F	−0.019839	0.699037	0.571807	0.059*	0.196 (3)
C22A	0.083 (3)	0.933 (3)	0.4313 (10)	0.035 (2)	0.196 (3)
H22D	0.102444	1.034030	0.440877	0.053*	0.196 (3)
H22E	−0.013882	0.921667	0.424344	0.053*	0.196 (3)
H22F	0.131343	0.905840	0.398021	0.053*	0.196 (3)
C23A	0.2596 (15)	0.836 (3)	0.5004 (8)	0.040 (3)	0.196 (3)
H23D	0.320334	0.885391	0.475125	0.060*	0.196 (3)
H23E	0.288775	0.735411	0.505731	0.060*	0.196 (3)
H23F	0.260857	0.886607	0.536101	0.060*	0.196 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0203 (2)	0.01784 (18)	0.01676 (18)	−0.00194 (14)	0.00182 (13)	0.00343 (13)
O1	0.0255 (6)	0.0321 (6)	0.0213 (6)	0.0003 (5)	0.0022 (5)	0.0035 (5)
O2	0.0273 (6)	0.0448 (7)	0.0209 (6)	0.0008 (5)	−0.0034 (5)	0.0087 (5)
C1	0.0164 (7)	0.0172 (7)	0.0166 (7)	0.0000 (5)	−0.0002 (5)	0.0038 (5)
C2	0.0179 (7)	0.0180 (7)	0.0161 (7)	0.0015 (5)	0.0010 (5)	0.0016 (5)
C3	0.0270 (8)	0.0231 (7)	0.0171 (7)	0.0010 (6)	0.0038 (6)	0.0013 (6)
C4	0.0355 (9)	0.0251 (8)	0.0196 (8)	0.0025 (7)	0.0030 (7)	−0.0056 (6)
C5	0.0334 (9)	0.0191 (7)	0.0293 (8)	−0.0021 (7)	0.0003 (7)	−0.0062 (6)
C6	0.0270 (8)	0.0180 (7)	0.0235 (8)	−0.0031 (6)	0.0029 (6)	0.0014 (6)
C7	0.0176 (7)	0.0161 (7)	0.0177 (7)	0.0009 (5)	−0.0002 (5)	0.0006 (5)
C8	0.0203 (8)	0.0197 (7)	0.0176 (7)	−0.0021 (6)	0.0019 (6)	0.0035 (6)
C9	0.0246 (8)	0.0144 (6)	0.0144 (7)	−0.0005 (6)	0.0046 (6)	0.0001 (5)
C10	0.0251 (8)	0.0206 (7)	0.0193 (7)	0.0002 (6)	0.0024 (6)	0.0030 (6)
C11	0.0246 (8)	0.0245 (8)	0.0264 (8)	−0.0031 (6)	0.0068 (7)	0.0019 (6)
C12	0.0337 (9)	0.0196 (7)	0.0211 (8)	−0.0006 (6)	0.0098 (7)	0.0030 (6)
C13	0.0333 (9)	0.0184 (7)	0.0153 (7)	0.0030 (6)	0.0047 (6)	0.0007 (5)
C14	0.0268 (8)	0.0169 (7)	0.0151 (7)	0.0013 (6)	0.0037 (6)	−0.0023 (5)
C15	0.0280 (8)	0.0181 (7)	0.0171 (7)	0.0030 (6)	0.0006 (6)	−0.0015 (6)
O3	0.0269 (12)	0.0420 (17)	0.0365 (11)	−0.0029 (11)	−0.0087 (9)	0.0098 (13)
N1	0.0231 (9)	0.0343 (10)	0.0281 (9)	0.0025 (8)	−0.0027 (7)	−0.0040 (8)
C16	0.0213 (10)	0.0370 (11)	0.0240 (10)	0.0014 (8)	0.0025 (8)	−0.0010 (8)
C17	0.033 (3)	0.0390 (15)	0.034 (3)	−0.0047 (13)	0.0030 (16)	0.0056 (16)
C18	0.0321 (19)	0.0303 (16)	0.048 (2)	0.0022 (14)	−0.0077 (14)	−0.0056 (14)
C19	0.0286 (19)	0.048 (2)	0.0311 (15)	0.0058 (17)	−0.0070 (13)	0.0038 (15)
O3A	0.027 (4)	0.042 (5)	0.037 (4)	0.000 (4)	−0.005 (3)	0.007 (4)
N1A	0.022 (2)	0.038 (2)	0.029 (2)	0.001 (2)	−0.001 (2)	0.001 (2)
C16A	0.023 (2)	0.037 (2)	0.029 (2)	0.002 (2)	0.002 (2)	−0.002 (2)
C17A	0.030 (5)	0.034 (4)	0.040 (5)	−0.002 (4)	−0.002 (4)	−0.005 (4)
C18A	0.022 (4)	0.043 (5)	0.036 (5)	−0.003 (4)	−0.008 (4)	0.001 (4)
C19A	0.024 (5)	0.042 (4)	0.033 (6)	−0.005 (4)	0.001 (4)	0.003 (4)
O4	0.0313 (10)	0.0784 (17)	0.0403 (11)	−0.0231 (11)	−0.0036 (8)	−0.0016 (11)
N2	0.0279 (10)	0.0325 (10)	0.0374 (11)	−0.0028 (8)	0.0053 (8)	0.0029 (8)
C20	0.0284 (11)	0.0387 (11)	0.0282 (10)	−0.0058 (9)	0.0042 (8)	−0.0080 (9)
C21	0.0410 (15)	0.040 (2)	0.0293 (17)	−0.0050 (15)	0.0059 (13)	0.0024 (12)
C22	0.056 (2)	0.070 (3)	0.040 (2)	−0.0181 (19)	0.0098 (19)	0.0103 (19)
C23	0.0215 (12)	0.0405 (18)	0.047 (2)	0.0020 (11)	−0.0001 (13)	−0.0004 (14)
O4A	0.033 (3)	0.063 (4)	0.052 (4)	−0.013 (3)	−0.004 (3)	−0.001 (4)
N2A	0.029 (2)	0.040 (2)	0.031 (2)	−0.001 (2)	0.004 (2)	0.001 (2)
C20A	0.032 (2)	0.045 (2)	0.034 (2)	−0.005 (2)	0.004 (2)	−0.002 (2)
C21A	0.043 (5)	0.037 (5)	0.038 (4)	−0.003 (4)	0.008 (4)	0.008 (4)
C22A	0.035 (5)	0.040 (5)	0.030 (5)	0.004 (4)	0.002 (4)	−0.005 (3)
C23A	0.028 (4)	0.051 (5)	0.042 (5)	0.002 (4)	0.005 (4)	0.003 (5)

Geometric parameters (Å, º) top

S1—C9	1.7721 (14)	C19—H19C	0.9800
S1—C8	1.8245 (15)	O3A—C16A	1.241 (12)
O1—C15	1.2169 (18)	N1A—C16A	1.318 (10)
O2—C15	1.3222 (18)	N1A—C19A	1.473 (14)
O2—H2	0.8400	N1A—C18A	1.477 (14)
C1—C7	1.406 (2)	C16A—C17A	1.497 (14)
C1—C2	1.408 (2)	C17A—H17D	0.9800
C1—C8	1.5086 (19)	C17A—H17E	0.9800
C2—C3	1.430 (2)	C17A—H17F	0.9800
C2—C7ⁱ	1.4405 (19)	C18A—H18D	0.9800
C3—C4	1.360 (2)	C18A—H18E	0.9800
C3—H3	0.9500	C18A—H18F	0.9800
C4—C5	1.412 (2)	C19A—H19D	0.9800
C4—H4	0.9500	C19A—H19E	0.9800
C5—C6	1.360 (2)	C19A—H19F	0.9800
C5—H5	0.9500	O4—C20	1.229 (3)
C6—C7ⁱ	1.431 (2)	N2—C20	1.339 (3)
C6—H6	0.9500	N2—C23	1.472 (4)
C8—H8A	0.9900	N2—C22	1.478 (6)
C8—H8B	0.9900	C20—C21	1.511 (4)
C9—C10	1.398 (2)	C21—H21A	0.9800
C9—C14	1.411 (2)	C21—H21B	0.9800
C10—C11	1.386 (2)	C21—H21C	0.9800
C10—H10	0.9500	C22—H22A	0.9800
C11—C12	1.382 (2)	C22—H22B	0.9800
C11—H11	0.9500	C22—H22C	0.9800
C12—C13	1.379 (2)	C23—H23A	0.9800
C12—H12	0.9500	C23—H23B	0.9800
C13—C14	1.402 (2)	C23—H23C	0.9800
C13—H13	0.9500	O4A—C20A	1.243 (10)
C14—C15	1.485 (2)	N2A—C20A	1.335 (10)
O3—C16	1.249 (4)	N2A—C23A	1.454 (13)
N1—C16	1.336 (3)	N2A—C22A	1.466 (13)
N1—C19	1.464 (5)	C20A—C21A	1.497 (13)
N1—C18	1.467 (5)	C21A—H21D	0.9800
C16—C17	1.502 (5)	C21A—H21E	0.9800
C17—H17A	0.9800	C21A—H21F	0.9800
C17—H17B	0.9800	C22A—H22D	0.9800
C17—H17C	0.9800	C22A—H22E	0.9800
C18—H18A	0.9800	C22A—H22F	0.9800
C18—H18B	0.9800	C23A—H23D	0.9800
C18—H18C	0.9800	C23A—H23E	0.9800
C19—H19A	0.9800	C23A—H23F	0.9800
C19—H19B	0.9800

C9—S1—C8	103.13 (7)	H19B—C19—H19C	109.5
C15—O2—H2	109.5	C16A—N1A—C19A	121.7 (14)
C7—C1—C2	120.14 (12)	C16A—N1A—C18A	124.4 (12)
C7—C1—C8	120.23 (13)	C19A—N1A—C18A	114.0 (16)
C2—C1—C8	119.57 (13)	O3A—C16A—N1A	122.5 (10)
C1—C2—C3	121.59 (13)	O3A—C16A—C17A	118.2 (12)
C1—C2—C7ⁱ	120.19 (13)	N1A—C16A—C17A	119.4 (11)
C3—C2—C7ⁱ	118.22 (13)	C16A—C17A—H17D	109.5
C4—C3—C2	121.46 (14)	C16A—C17A—H17E	109.5
C4—C3—H3	119.3	H17D—C17A—H17E	109.5
C2—C3—H3	119.3	C16A—C17A—H17F	109.5
C3—C4—C5	120.48 (14)	H17D—C17A—H17F	109.5
C3—C4—H4	119.8	H17E—C17A—H17F	109.5
C5—C4—H4	119.8	N1A—C18A—H18D	109.5
C6—C5—C4	120.22 (14)	N1A—C18A—H18E	109.5
C6—C5—H5	119.9	H18D—C18A—H18E	109.5
C4—C5—H5	119.9	N1A—C18A—H18F	109.5
C5—C6—C7ⁱ	121.72 (14)	H18D—C18A—H18F	109.5
C5—C6—H6	119.1	H18E—C18A—H18F	109.5
C7ⁱ—C6—H6	119.1	N1A—C19A—H19D	109.5
C1—C7—C6ⁱ	122.42 (13)	N1A—C19A—H19E	109.5
C1—C7—C2ⁱ	119.68 (13)	H19D—C19A—H19E	109.5
C6ⁱ—C7—C2ⁱ	117.90 (13)	N1A—C19A—H19F	109.5
C1—C8—S1	104.70 (10)	H19D—C19A—H19F	109.5
C1—C8—H8A	110.8	H19E—C19A—H19F	109.5
S1—C8—H8A	110.8	C20—N2—C23	122.1 (3)
C1—C8—H8B	110.8	C20—N2—C22	120.4 (3)
S1—C8—H8B	110.8	C23—N2—C22	117.5 (4)
H8A—C8—H8B	108.9	O4—C20—N2	121.6 (2)
C10—C9—C14	118.61 (13)	O4—C20—C21	121.4 (3)
C10—C9—S1	121.23 (11)	N2—C20—C21	116.9 (3)
C14—C9—S1	120.16 (11)	C20—C21—H21A	109.5
C11—C10—C9	120.66 (14)	C20—C21—H21B	109.5
C11—C10—H10	119.7	H21A—C21—H21B	109.5
C9—C10—H10	119.7	C20—C21—H21C	109.5
C12—C11—C10	120.88 (15)	H21A—C21—H21C	109.5
C12—C11—H11	119.6	H21B—C21—H21C	109.5
C10—C11—H11	119.6	N2—C22—H22A	109.5
C13—C12—C11	119.28 (14)	N2—C22—H22B	109.5
C13—C12—H12	120.4	H22A—C22—H22B	109.5
C11—C12—H12	120.4	N2—C22—H22C	109.5
C12—C13—C14	121.20 (14)	H22A—C22—H22C	109.5
C12—C13—H13	119.4	H22B—C22—H22C	109.5
C14—C13—H13	119.4	N2—C23—H23A	109.5
C13—C14—C9	119.34 (14)	N2—C23—H23B	109.5
C13—C14—C15	119.55 (13)	H23A—C23—H23B	109.5
C9—C14—C15	121.04 (13)	N2—C23—H23C	109.5
O1—C15—O2	122.88 (15)	H23A—C23—H23C	109.5
O1—C15—C14	122.95 (14)	H23B—C23—H23C	109.5
O2—C15—C14	114.17 (13)	C20A—N2A—C23A	119.4 (12)
C16—N1—C19	124.1 (3)	C20A—N2A—C22A	116.6 (11)
C16—N1—C18	119.9 (3)	C23A—N2A—C22A	123.3 (14)
C19—N1—C18	115.9 (3)	O4A—C20A—N2A	122.7 (9)
O3—C16—N1	120.5 (2)	O4A—C20A—C21A	122.7 (13)
O3—C16—C17	120.8 (3)	N2A—C20A—C21A	109.7 (12)
N1—C16—C17	118.7 (3)	C20A—C21A—H21D	109.5
C16—C17—H17A	109.5	C20A—C21A—H21E	109.5
C16—C17—H17B	109.5	H21D—C21A—H21E	109.5
H17A—C17—H17B	109.5	C20A—C21A—H21F	109.5
C16—C17—H17C	109.5	H21D—C21A—H21F	109.5
H17A—C17—H17C	109.5	H21E—C21A—H21F	109.5
H17B—C17—H17C	109.5	N2A—C22A—H22D	109.5
N1—C18—H18A	109.5	N2A—C22A—H22E	109.5
N1—C18—H18B	109.5	H22D—C22A—H22E	109.5
H18A—C18—H18B	109.5	N2A—C22A—H22F	109.5
N1—C18—H18C	109.5	H22D—C22A—H22F	109.5
H18A—C18—H18C	109.5	H22E—C22A—H22F	109.5
H18B—C18—H18C	109.5	N2A—C23A—H23D	109.5
N1—C19—H19A	109.5	N2A—C23A—H23E	109.5
N1—C19—H19B	109.5	H23D—C23A—H23E	109.5
H19A—C19—H19B	109.5	N2A—C23A—H23F	109.5
N1—C19—H19C	109.5	H23D—C23A—H23F	109.5
H19A—C19—H19C	109.5	H23E—C23A—H23F	109.5

C7—C1—C2—C3	−179.61 (14)	C10—C9—C14—C13	−0.2 (2)
C8—C1—C2—C3	3.3 (2)	S1—C9—C14—C13	179.70 (11)
C7—C1—C2—C7ⁱ	−0.1 (2)	C10—C9—C14—C15	−177.18 (13)
C8—C1—C2—C7ⁱ	−177.13 (13)	S1—C9—C14—C15	2.68 (19)
C1—C2—C3—C4	179.07 (15)	C13—C14—C15—O1	−164.05 (14)
C7ⁱ—C2—C3—C4	−0.5 (2)	C9—C14—C15—O1	13.0 (2)
C2—C3—C4—C5	0.4 (2)	C13—C14—C15—O2	15.89 (19)
C3—C4—C5—C6	−0.3 (3)	C9—C14—C15—O2	−167.10 (13)
C4—C5—C6—C7ⁱ	0.2 (3)	C19—N1—C16—O3	178.2 (5)
C2—C1—C7—C6ⁱ	−179.13 (14)	C18—N1—C16—O3	3.2 (6)
C8—C1—C7—C6ⁱ	−2.1 (2)	C19—N1—C16—C17	−0.5 (7)
C2—C1—C7—C2ⁱ	0.1 (2)	C18—N1—C16—C17	−175.6 (6)
C8—C1—C7—C2ⁱ	177.11 (13)	C19A—N1A—C16A—O3A	−1 (3)
C7—C1—C8—S1	−95.52 (14)	C18A—N1A—C16A—O3A	180 (2)
C2—C1—C8—S1	81.56 (14)	C19A—N1A—C16A—C17A	−180 (3)
C9—S1—C8—C1	178.13 (9)	C18A—N1A—C16A—C17A	0 (3)
C8—S1—C9—C10	−11.00 (14)	C23—N2—C20—O4	−174.3 (3)
C8—S1—C9—C14	169.14 (11)	C22—N2—C20—O4	4.3 (4)
C14—C9—C10—C11	1.3 (2)	C23—N2—C20—C21	5.4 (5)
S1—C9—C10—C11	−178.57 (12)	C22—N2—C20—C21	−175.9 (4)
C9—C10—C11—C12	−1.0 (2)	C23A—N2A—C20A—O4A	−171.1 (13)
C10—C11—C12—C13	−0.5 (2)	C22A—N2A—C20A—O4A	0 (2)
C11—C12—C13—C14	1.6 (2)	C23A—N2A—C20A—C21A	33.2 (17)
C12—C13—C14—C9	−1.3 (2)	C22A—N2A—C20A—C21A	−155.7 (19)
C12—C13—C14—C15	175.77 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring of (1).

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3Aⁱⁱ	0.84	1.94	2.770 (14)	169
C8—H8B···O4Aⁱⁱⁱ	0.99	2.48	3.126 (8)	122
C17—H17A···O4^iv	0.98	2.62	3.518 (8)	152
C18A—H18D···S1^iv	0.98	3.02	3.83 (3)	142
C19A—H19E···O4A^iv	0.98	2.43	3.40 (4)	168
C21—H21C···O1	0.98	2.49	3.422 (7)	158
C22A—H22F···O1	0.98	2.54	3.51 (3)	168
C4—H4···Cg1	0.95	2.76	3.49	135

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

4,4'-{[Anthracene-9,10-diylbis(methylene)]bis(oxy)}dibenzoic acid dimethylformamide disolvate (2) top

Crystal data top

C₃₀H₂₂O₆·2C₃H₇NO	F(000) = 660
M_r = 624.67	D_x = 1.347 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.8761 (10) Å	Cell parameters from 1406 reflections
b = 9.6711 (9) Å	θ = 2.6–18.7°
c = 14.8968 (14) Å	µ = 0.10 mm⁻¹
β = 100.519 (3)°	T = 104 K
V = 1540.6 (2) Å³	Plate, clear yellowish yellow
Z = 2	0.26 × 0.19 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	1669 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.179
Absorption correction: multi-scan (Olex2; Dolomanov et al., 2009)	θ_max = 26.5°, θ_min = 2.1°
T_min = 0.666, T_max = 0.745	h = −13→13
49734 measured reflections	k = −12→12
3169 independent reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0696P)² + 0.9349P] where P = (F_o² + 2F_c²)/3
3169 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.4625 (2)	0.3352 (2)	0.09997 (14)	0.0337 (6)
O2	0.3683 (2)	0.8009 (2)	0.38061 (15)	0.0411 (6)
O3	0.4259 (2)	0.9259 (2)	0.26840 (16)	0.0466 (7)
H3	0.420178	0.991287	0.304515	0.070*
O4	0.4165 (2)	1.1349 (2)	0.37398 (17)	0.0503 (7)
N1	0.3426 (3)	1.1942 (3)	0.50255 (19)	0.0422 (7)
C7	0.3906 (3)	0.0820 (3)	−0.0203 (2)	0.0250 (7)
C1	0.4710 (3)	0.0961 (3)	0.0652 (2)	0.0255 (7)
C9	0.4409 (3)	0.4460 (3)	0.1518 (2)	0.0303 (8)
C2	0.5807 (3)	0.0166 (3)	0.0859 (2)	0.0259 (7)
C13	0.3834 (3)	0.5569 (3)	0.2809 (2)	0.0316 (8)
H13	0.353304	0.551391	0.336760	0.038*
C14	0.3968 (3)	0.4365 (3)	0.2335 (2)	0.0313 (8)
H14	0.376246	0.349338	0.256255	0.038*
C6	0.7205 (3)	−0.1639 (3)	0.0447 (2)	0.0312 (8)
H6	0.740356	−0.229858	0.002326	0.037*
C8	0.4362 (3)	0.1987 (3)	0.1318 (2)	0.0299 (7)
H8A	0.346404	0.190190	0.134842	0.036*
H8B	0.485761	0.181983	0.193453	0.036*
C3	0.6662 (3)	0.0280 (3)	0.1708 (2)	0.0336 (8)
H3A	0.649564	0.092861	0.215009	0.040*
C15	0.4000 (3)	0.8076 (3)	0.3059 (2)	0.0368 (8)
C12	0.4126 (3)	0.6845 (3)	0.2495 (2)	0.0309 (8)
C10	0.4707 (3)	0.5746 (3)	0.1194 (2)	0.0335 (8)
H10	0.501582	0.580681	0.063815	0.040*
C11	0.4557 (3)	0.6929 (3)	0.1676 (2)	0.0354 (8)
H11	0.474846	0.780492	0.144782	0.042*
C5	0.7977 (3)	−0.1500 (4)	0.1261 (2)	0.0378 (8)
H5	0.870193	−0.206227	0.140562	0.045*
C4	0.7702 (3)	−0.0514 (4)	0.1897 (2)	0.0410 (9)
H4	0.825451	−0.040790	0.246538	0.049*
C16	0.3683 (3)	1.1049 (4)	0.4424 (3)	0.0443 (9)
H16	0.349206	1.010445	0.450942	0.053*
C17	0.3683 (4)	1.3394 (4)	0.4945 (3)	0.0541 (11)
H17A	0.433156	1.351418	0.457255	0.081*
H17B	0.397436	1.378518	0.555323	0.081*
H17C	0.291892	1.387089	0.465295	0.081*
C18	0.2832 (4)	1.1503 (4)	0.5779 (3)	0.0540 (11)
H18A	0.198205	1.188036	0.569478	0.081*
H18B	0.331843	1.184320	0.635586	0.081*
H18C	0.279500	1.049111	0.579376	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0475 (14)	0.0227 (12)	0.0350 (12)	−0.0027 (10)	0.0182 (10)	−0.0034 (10)
O2	0.0483 (15)	0.0389 (14)	0.0400 (14)	−0.0043 (11)	0.0181 (12)	−0.0065 (11)
O3	0.0656 (17)	0.0302 (14)	0.0507 (15)	−0.0051 (12)	0.0288 (14)	−0.0078 (12)
O4	0.0652 (17)	0.0386 (15)	0.0510 (16)	−0.0080 (13)	0.0210 (14)	−0.0086 (12)
N1	0.0441 (18)	0.0409 (19)	0.0423 (17)	0.0027 (14)	0.0098 (14)	−0.0051 (15)
C7	0.0250 (16)	0.0212 (16)	0.0303 (17)	−0.0032 (13)	0.0094 (14)	0.0010 (13)
C1	0.0303 (17)	0.0182 (16)	0.0307 (18)	−0.0031 (13)	0.0127 (14)	0.0004 (13)
C9	0.0343 (18)	0.0233 (18)	0.0336 (18)	−0.0003 (14)	0.0067 (15)	−0.0047 (14)
C2	0.0303 (17)	0.0198 (17)	0.0288 (17)	−0.0061 (13)	0.0087 (14)	0.0007 (13)
C13	0.0363 (19)	0.0305 (19)	0.0299 (18)	−0.0025 (15)	0.0111 (15)	−0.0001 (15)
C14	0.0357 (18)	0.0251 (18)	0.0342 (19)	−0.0054 (14)	0.0092 (15)	0.0015 (14)
C6	0.0329 (18)	0.0256 (18)	0.0373 (19)	0.0005 (14)	0.0123 (15)	0.0019 (14)
C8	0.0346 (18)	0.0242 (18)	0.0318 (17)	−0.0009 (14)	0.0087 (14)	0.0019 (14)
C3	0.0365 (19)	0.034 (2)	0.0316 (19)	−0.0036 (16)	0.0103 (15)	−0.0064 (15)
C15	0.039 (2)	0.033 (2)	0.041 (2)	−0.0043 (16)	0.0153 (17)	−0.0025 (17)
C12	0.0315 (18)	0.0288 (19)	0.0338 (18)	−0.0002 (14)	0.0096 (14)	−0.0025 (15)
C10	0.041 (2)	0.033 (2)	0.0285 (18)	−0.0005 (15)	0.0106 (15)	−0.0011 (15)
C11	0.042 (2)	0.0290 (19)	0.0372 (19)	−0.0008 (15)	0.0112 (16)	0.0018 (16)
C5	0.0330 (19)	0.042 (2)	0.039 (2)	0.0063 (16)	0.0078 (16)	0.0054 (17)
C4	0.035 (2)	0.052 (2)	0.034 (2)	0.0015 (18)	0.0020 (16)	−0.0005 (17)
C16	0.042 (2)	0.040 (2)	0.052 (2)	−0.0043 (17)	0.0091 (19)	−0.0013 (19)
C17	0.075 (3)	0.039 (2)	0.052 (2)	0.004 (2)	0.019 (2)	−0.0032 (18)
C18	0.062 (3)	0.057 (3)	0.050 (2)	−0.001 (2)	0.026 (2)	0.001 (2)

Geometric parameters (Å, º) top

O1—C9	1.366 (3)	C6—C5	1.348 (4)
O1—C8	1.448 (3)	C6—H6	0.9500
O2—C15	1.225 (4)	C8—H8A	0.9900
O3—C15	1.326 (4)	C8—H8B	0.9900
O3—H3	0.8400	C3—C4	1.353 (4)
O4—C16	1.262 (4)	C3—H3A	0.9500
N1—C16	1.311 (4)	C15—C12	1.477 (4)
N1—C17	1.442 (5)	C12—C11	1.387 (4)
N1—C18	1.457 (4)	C10—C11	1.377 (4)
C7—C1	1.414 (4)	C10—H10	0.9500
C7—C6ⁱ	1.435 (4)	C11—H11	0.9500
C7—C2ⁱ	1.439 (4)	C5—C4	1.415 (5)
C1—C2	1.405 (4)	C5—H5	0.9500
C1—C8	1.499 (4)	C4—H4	0.9500
C9—C14	1.391 (4)	C16—H16	0.9500
C9—C10	1.394 (4)	C17—H17A	0.9800
C2—C3	1.431 (4)	C17—H17B	0.9800
C13—C12	1.377 (4)	C17—H17C	0.9800
C13—C14	1.383 (4)	C18—H18A	0.9800
C13—H13	0.9500	C18—H18B	0.9800
C14—H14	0.9500	C18—H18C	0.9800

C9—O1—C8	117.8 (2)	C2—C3—H3A	119.2
C15—O3—H3	109.5	O2—C15—O3	123.0 (3)
C16—N1—C17	121.1 (3)	O2—C15—C12	123.0 (3)
C16—N1—C18	121.0 (3)	O3—C15—C12	114.0 (3)
C17—N1—C18	117.9 (3)	C13—C12—C11	119.1 (3)
C1—C7—C6ⁱ	121.9 (3)	C13—C12—C15	118.6 (3)
C1—C7—C2ⁱ	120.0 (3)	C11—C12—C15	122.3 (3)
C6ⁱ—C7—C2ⁱ	118.1 (3)	C11—C10—C9	120.2 (3)
C2—C1—C7	120.4 (3)	C11—C10—H10	119.9
C2—C1—C8	121.6 (3)	C9—C10—H10	119.9
C7—C1—C8	118.1 (3)	C10—C11—C12	120.1 (3)
O1—C9—C14	124.4 (3)	C10—C11—H11	119.9
O1—C9—C10	115.5 (3)	C12—C11—H11	119.9
C14—C9—C10	120.1 (3)	C6—C5—C4	119.8 (3)
C1—C2—C3	122.7 (3)	C6—C5—H5	120.1
C1—C2—C7ⁱ	119.6 (3)	C4—C5—H5	120.1
C3—C2—C7ⁱ	117.7 (3)	C3—C4—C5	120.9 (3)
C12—C13—C14	122.0 (3)	C3—C4—H4	119.5
C12—C13—H13	119.0	C5—C4—H4	119.5
C14—C13—H13	119.0	O4—C16—N1	124.9 (3)
C13—C14—C9	118.4 (3)	O4—C16—H16	117.6
C13—C14—H14	120.8	N1—C16—H16	117.6
C9—C14—H14	120.8	N1—C17—H17A	109.5
C5—C6—C7ⁱ	122.0 (3)	N1—C17—H17B	109.5
C5—C6—H6	119.0	H17A—C17—H17B	109.5
C7ⁱ—C6—H6	119.0	N1—C17—H17C	109.5
O1—C8—C1	107.4 (2)	H17A—C17—H17C	109.5
O1—C8—H8A	110.2	H17B—C17—H17C	109.5
C1—C8—H8A	110.2	N1—C18—H18A	109.5
O1—C8—H8B	110.2	N1—C18—H18B	109.5
C1—C8—H8B	110.2	H18A—C18—H18B	109.5
H8A—C8—H8B	108.5	N1—C18—H18C	109.5
C4—C3—C2	121.6 (3)	H18A—C18—H18C	109.5
C4—C3—H3A	119.2	H18B—C18—H18C	109.5

C6ⁱ—C7—C1—C2	−178.4 (3)	C7ⁱ—C2—C3—C4	−0.5 (4)
C2ⁱ—C7—C1—C2	1.5 (4)	C14—C13—C12—C11	0.5 (5)
C6ⁱ—C7—C1—C8	1.0 (4)	C14—C13—C12—C15	−177.8 (3)
C2ⁱ—C7—C1—C8	−179.1 (2)	O2—C15—C12—C13	2.2 (5)
C8—O1—C9—C14	0.8 (4)	O3—C15—C12—C13	−177.7 (3)
C8—O1—C9—C10	178.4 (3)	O2—C15—C12—C11	−176.1 (3)
C7—C1—C2—C3	179.2 (3)	O3—C15—C12—C11	4.0 (5)
C8—C1—C2—C3	−0.2 (4)	O1—C9—C10—C11	−178.3 (3)
C7—C1—C2—C7ⁱ	−1.5 (4)	C14—C9—C10—C11	−0.6 (5)
C8—C1—C2—C7ⁱ	179.2 (3)	C9—C10—C11—C12	1.0 (5)
C12—C13—C14—C9	0.0 (5)	C13—C12—C11—C10	−1.0 (5)
O1—C9—C14—C13	177.6 (3)	C15—C12—C11—C10	177.3 (3)
C10—C9—C14—C13	0.1 (5)	C7ⁱ—C6—C5—C4	−0.6 (5)
C9—O1—C8—C1	−178.3 (2)	C2—C3—C4—C5	−0.6 (5)
C2—C1—C8—O1	104.5 (3)	C6—C5—C4—C3	1.1 (5)
C7—C1—C8—O1	−74.8 (3)	C17—N1—C16—O4	0.2 (5)
C1—C2—C3—C4	178.9 (3)	C18—N1—C16—O4	178.0 (3)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C9–C14 ring of (2).

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.84	1.74	2.575 (3)	175
C8—H8A···O2ⁱⁱ	0.99	2.54	3.429 (4)	149
C16—H16···O2	0.95	2.31	3.080 (4)	138
C4—H4···Cg2	0.95	3.07	3.96	157

Symmetry code: (ii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

The authors are thankful to the DRDO, New Delhi, India for financial support and to the DST-FIST for Single Crystal X-ray facilities in the Department of chemistry, IIT Roorkee. Shagun Kushwaha is grateful to the DST, Govt. of India for the Inspire fellowship and Amit Thapaliyal to the IIT Roorkee for the Institute fellowship.

Funding information

Funding for this research was provided by: Life Sciences Research Board (grant No. LSRB-419 to Prof. U.P. Singh).

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Volume 81| Part 11| November 2025| Pages 1063-1066

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

Syntheses and structures of two anthracene–benzoic acid derivatives as potential MOF linkers

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

3. Supramolecular features