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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 75| Part 4| April 2019| Pages 475-481
https://doi.org/10.1107/S205698901900375X

A 1:1:1 co-crystal solvate comprising 2,2′-di­thiodi­benzoic acid, 2-chloro­benzoic acid and N,N-di­methyl­formamide: crystal structure, Hirshfeld surface analysis and computational study

CROSSMARK_Color_square_no_text.svg
Sang Loon Tana and Edward R. T. Tiekinka*

aResearch Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
*Correspondence e-mail: edwardt@sunway.edu.my

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 6 March 2019; accepted 19 March 2019; online 26 March 2019)

The asymmetric unit of the three-component title compound, 2,2′-di­thiodi­benzoic acid–2-chloro­benzoic acid–N,N-di­methyl­formamide (1/1/1), C14H10O4S2·C7H5ClO2·C3H7NO, contains a mol­ecule each of 2,2′-di­thiodi­benzoic acid (DTBA), 2-chloro­benzoic acid (2CBA) and di­methyl­formamide (DMF). The DTBA mol­ecule is twisted [the C—S—S—C torsion angle is 88.37 (17)°] and each carb­oxy­lic group is slightly twisted from the benzene ring to which it is connected [CO2/C6 dihedral angles = 7.6 (3) and 12.5 (3)°]. A small twist is evident in the mol­ecule of 2CBA [CO2/C6 dihedral angle = 4.4 (4)°]. In the crystal, the three mol­ecules are connected by hydrogen bonds with the two carb­oxy­lic acid residues derived from DTBA and 2CBA forming a non-symmetric eight-membered {⋯HOCO}2 synthon, and the second carb­oxy­lic acid of DTBA linked to the DMF mol­ecule via a seven-membered {⋯HOCO⋯HCO} heterosynthon. The three-mol­ecule aggregates are connected into a supra­molecular chain along the a axis via DTBA-C—H⋯O(hydroxyl-2CBA), 2CBA-C—H⋯O(hydroxyl-DTBA) and DTBA-C—H⋯S(DTBA) inter­actions. Supra­molecular layers in the ab plane are formed as the chains are linked via DMF-C—H⋯S(DTBA) contacts, and these inter-digitate along the c-axis direction without specific points of contact between them. A Hirshfeld surface analysis points to additional but, weak contacts to stabilize the three-dimensional architecture: DTBA-C=O⋯H(phenyl-DTBA), 2CBA-Cl⋯H(phenyl-DTBA), as well as a π–π contact between the delocalized eight-membered {⋯HOC=O}2 carb­oxy­lic dimer and the phenyl ring of 2CBA. The latter was confirmed by electrostatic potential (ESP) mapping.

CCDC reference: 1903993

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1. Chemical context

Recent bibliographic reviews have highlighted the rich coord­ination chemistry based on ligands derived from 2-mercapto­benzoic acid (2-MBA) (Wehr-Candler & Henderson, 2016[Wehr-Candler, T. & Henderson, W. (2016). Coord. Chem. Rev. 313, 111-155.]) and its 3- and 4-isomeric analogues (Tiekink & Henderson, 2017[Tiekink, E. R. T. & Henderson, W. (2017). Coord. Chem. Rev. 341, 19-52.]). By contrast, co-crystal formation with these mol­ecules is quite limited with the only co-crystal of an n-MBA mol­ecule being that formed between 2-MBA and its oxidation product 2,2′-di­thiodi­benzoic acid (DTBA) (Rowland et al., 2011[Rowland, C. E., Cantos, P. M., Toby, B. H., Frisch, M., Deschamps, J. R. & Cahill, C. L. (2011). Cryst. Growth Des. 11, 1370-1374.]). One reason for the scarcity of co-crystals containing 2-MBA is the propensity for the acid to be oxidized, to generate DTBA, during co-crystallization experiments with bipyridyl-type mol­ecules (Broker & Tiekink, 2007[Broker, G. A. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 1096-1109.]) and with other carb­oxy­lic acids (Tan & Tiekink, 2019a[Tan, S. L. & Tiekink, E. R. T. (2019a). Acta Cryst. E75, 1-7.]). Another, less common, outcome of crystallization experiments with 2-MBA is the sulfur extrusion product, 2,2′-thiodi­benzoic acid (Tan & Tiekink, 2018[Tan, S. L. & Tiekink, E. R. T. (2018). Acta Cryst. E74, 1764-1771.]; Gorobet et al., 2018[Gorobet, A., Vitiu, A., Petuhov, O. & Croitor, L. (2018). Polyhedron, 151, 51-57.]). Herein, another unexpected product from a co-crystallization experiment involving 2-MBA is described. While the now anti­ci­pated coformer DTBA was observed after the co-cryst­allization of 2-MBA with 2-chloro­benzoic acid (2CBA), and recrystallization from a toluene/di­methyl­formamide solution (50:50 v/v), a solvent di­methyl­formamide mol­ecule was also found in the resultant co-crystal solvate. In this three-component crystal, one of the carb­oxy­lic acid groups of the DTBA mol­ecule forms hydrogen bonds to DMF rather than to 2CBA. Herein, the crystal and mol­ecular structures of the title co-crystal solvate are described along with an analysis of the calculated Hirshfeld surfaces and a computational chemistry study.

[Scheme 1]

2. Structural commentary

The title compound, (I)[link], was isolated from the co-crystallization of 2-mercapto­benzoic acid and 2-chloro­benzoic acid prepared through solvent-assisted (methanol) grinding, followed by recrystallization from a toluene/di­methyl­formamide solution (50:50 v/v). The asymmetric unit comprises 2,2′-di­thiodi­benzoic acid (DTBA), 2-chloro­benzoic acid (2CBA) and a di­methyl­formamide (DMF) solvent mol­ecule in a stoichiometric 1:1:1 ratio, as illustrated in Fig. 1[link]; each mol­ecule is in a general position.

[Figure 1]
Figure 1
The mol­ecular structures of (a) 2,2′-di­thiodi­benzoic acid, (b) 2-chloro­benzoic acid and (c) di­methyl­formamide in (I)[link], showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

As anti­cipated, crystallography reveals that the original 2-mercapto­benzoic acid underwent oxidation to yield a mol­ecule of DTBA, with the benzoic acid moieties being bridged through a di­sulfide bond [S1—S2 = 2.053 (1) Å]. The presence of carb­oxy­lic acid groups is confirmed by the disparity in the bond lengths for C8—O4, O3 [1.317 (4) and 1.229 (4) Å] and C21—O6, O5 [1.326 (4) and 1.209 (4) Å]. Both carb­oxy­lic acid groups (O3—C8—O4 and O5—C21—O6) are slightly twisted from the benzene rings (C9/C14 and C15/C20) to which they are bonded with the corresponding dihedral angles being 7.6 (3) and 12.5 (3)°, respectively. The C14—S1—S2—C15 torsion angle is 88.37 (17)°, indicating an almost orthogonal disposition between the benzene rings. The carbonyl-O3 and O5 atoms are oriented towards the di­sulfide-S1 and S2 atoms with S1⋯O3 and S2⋯O5 distances of 2.713 (2) and 2.661 (3) Å, respectively, and are indicative of hypervalent S←O inter­actions (Nakanishi et al., 2007[Nakanishi, W., Nakamoto, T., Hayashi, S., Sasamori, T. & Tokitoh, N. (2007). Chem. Eur. J. 13, 255-268.]).

As for DTBA, the confirmation that 2CBA exists as a carb­oxy­lic acid is readily ascertained by the difference observed in the C1—O1, O2 bond lengths of 1.222 (4) and 1.320 (4), respectively. The carb­oxy­lic acid group is almost co-planar with the phenyl ring (C2–C7) as seen in the dihedral angle of 4.4 (4)° between their planes. Similarly, co-planarity is also noted between the chloride atom and benzene ring plane with the r.m.s deviation from the least-squares plane through the seven non-hydrogen atoms being 0.027 Å.

3. Supra­molecular features

The geometric parameters characterizing the inter­atomic contacts in the crystal of (I)[link], as identified in PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), are given in Table 1[link]. Some of the main contacts in the mol­ecular packing provide direct links between DTBA, 2CBA and DMF mol­ecules, in that hydrogen bonds are formed between one of the terminal carb­oxy­lic groups of DTBA and 2CBA, and between the other carb­oxy­lic acid terminus with the carbonyl group of DMF. The former inter­action leads to a classical, but non-symmetric eight-membered {⋯HOCO}2 homosynthon while the latter results in a seven-membered {⋯HOCO⋯HCO} heterosynthon when the C22—H22⋯O5 inter­action is taken into account, Fig. 2[link](a).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2O⋯O3 0.83 (6) 1.86 (7) 2.687 (4) 176 (9)
O4—H4O⋯O1 0.73 (7) 1.88 (6) 2.612 (4) 175 (5)
O6—H6O⋯O7 0.87 (5) 1.73 (5) 2.594 (4) 172 (5)
C3—H3⋯O4i 0.95 2.57 3.363 (5) 142
C10—H10⋯O2ii 0.95 2.54 3.331 (5) 141
C11—H11⋯S1ii 0.95 2.83 3.544 (4) 133
C22—H22⋯O5 0.95 2.33 3.095 (5) 138
C24—H24B⋯S2iii 0.98 2.83 3.531 (4) 129
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) -x+1, -y, -z+1.
[Figure 2]
Figure 2
Mol­ecular packing in (I)[link]: (a) a view of the three-mol­ecule aggregate with the O—H⋯O hydrogen bonds and C—H⋯O inter­actions shown as orange and blue dashed lines, respectively, (b) supra­molecular chains aligned along the a axis with the C—H⋯S inter­actions shown as purple dashed lines and (c) a view of the unit-cell contents in perspective down the a axis.

The resultant three-mol­ecule aggregates are connected by DTBA-C10—H10⋯O2(hydroxyl-2CBA) and 2CBA-C3—H3⋯O4(hydroxyl-DTBA) inter­actions to form a non-symmetric, ten-membered {⋯OCCCH}2 homosynthon, as well as discrete DTBA-C11—H11⋯S1(DTBA) inter­actions. These lead to a supra­molecular chain along the crystallographic a direction, as indicated in Fig. 2[link](b). Inter­actions between the chains leading to a layer in the ab plane occur through DMF-C24—H24C⋯S2(DTBA) contacts, Fig. 2[link](c). The layers inter-digitate along the c-axis direction with only weak contacts between them as detailed in the next section.

4. Hirshfeld surface analysis

To better understand the nature of the inter­molecular inter­actions in the crystal of (I)[link], the individual mol­ecules comprising the asymmetric unit as well as the contents of the asymmetric unit were subjected to Hirshfeld surface analysis using Crystal Explorer 17 (Turner et al., 2017[Turner, M. J., Mckinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). Crystal Explorer 17. The University of Western Australia.]) and based on the procedures described in the literature (Tan et al., 2019[Tan, S. L., Jotani, M. M. & Tiekink, E. R. T. (2019). Acta Cryst. E75, 308-318.]).

The dnorm maps of the respective mol­ecules in the aggregates are shown in Fig. 3[link]. DTBA exhibits several intense red spots on the dnorm map signifying close contacts which origin­ate from DTBA-O—H⋯O(carbonyl-2CBA), DTBA-O—H⋯O(carbonyl-DMF), DTBA-C=O⋯H(hydroxyl-2CBA) and DTBA-C=O⋯H(DMF). Other red spots are observed through the dnorm map, albeit with relatively weak intensity. The contacts are consistent with those identified above except for some additional inter­actions such as DTBA-C=O⋯H(phenyl-DTBA), 2CBA-Cl⋯H(phenyl-DTBA) as well as a π–π contact between the delocalized eight-membered {⋯HOC=O}2 carb­oxy­lic dimer and the phenyl ring of 2CBA, Fig. 3[link](b). To validate the non-conventional π–π contact, the inter­acting mol­ecules were subjected to electrostatic potential (ESP) mapping using Spartan'16 (Spartan'16, 2017[Spartan'16 (2017). Spartan'16. Wavefunction, Inc. Irvine, CA.]) by treating the DTBA dimer as a single entity through a DFT-B3LYP/6-311+G(d,p) level of theory. The ESP mapping shows that the dimeric ring ranges from electropositive to neutral within the centre of the ring while the phenyl ring of 2CBA is mainly neutral indicating that the inter­action is mainly diffusive in nature, Fig. 3[link](c) and (d). As for the 2CBA and DMF mol­ecules, the corresponding dnorm maps (not shown) are reflective of their inter­actions with the DTBA mol­ecule.

[Figure 3]
Figure 3
(a) and (b) Two views of the dnorm map of the DTBA mol­ecule within the range −0.274 to +0.862 arbitrary units, showing the short contacts highlighted as red spots with the intensity relative to the contact distances. Hydrogen bonds are indicated as green dashed lines and π–π contacts are highlighted as yellow dashed lines. ESPs map of (c) the DTBA dimer and (d) 2CBA, with the isosurface value scaled from −0.019 to +0.019 atomic units.

The two-dimensional fingerprint plots were generated to qu­antify the close contacts identified on the Hirshfeld surfaces. The overall fingerprint plot of (I)[link] and the corresponding plots of the individual components are shown in Fig. 4[link]. In general, (I)[link] exhibits a shield-like profile in the overall fingerprint plot without any obvious spikes unlike the individual components. This indicates the discrete nature of the three-mol­ecule aggregate sustained by hydrogen bonding. Decomposition of the full fingerprint plots of (I)[link] shows that the contacts are mainly dominated by H⋯H (34.3%; di + de ∼2.20 Å), O⋯H/H⋯O (18.4%; di + de ∼2.44 Å), C⋯H/H⋯C (18.0%; di + de ∼2.86 Å), S⋯H/H⋯S (8.2%; di + de ∼2.74 Å), Cl⋯H/H⋯Cl (7.2%; di + de ∼2.72 Å) and other contacts (14.0%). Almost all of these contacts are shorter than their corres­ponding sum van der Waals radii, with H⋯H, O⋯H, C⋯H, S⋯H and Cl⋯H being ∼2.4, ∼2.72, ∼2.9, ∼3.0 and ∼2.95 Å, respectively.

[Figure 4]
Figure 4
(a) The overall two-dimensional fingerprint plots for the DTBA, 2CBA and DMF mol­ecules and entire (I)[link], and those delineated into (b) H⋯H, (c) H⋯O/ O⋯H, (d) H⋯C/ C⋯H, (e) H⋯S/ S⋯H and (f) H⋯Cl/ Cl⋯H contacts, with the percentage contribution being specified for each contact.

The DTBA and 2CBA mol­ecules display similar fingerprint patterns having a claw-like profile in the respective full fingerprint plots, implying the existence of nearly identical inter­actions between the mol­ecules which is expected considering the similarity of their mol­ecular structures. Detailed analysis of the decomposed fingerprint plots shows that H⋯H is the most prevalent contact for the mol­ecules, with the percentage contribution to the overall contacts of 29.7 and 25.0% and minimum di + de contact distance of ∼2.18 and ∼2.24 Å for DTBA and 2CBA, respectively. The O⋯H/H⋯O contacts are the second most dominant contact for the individual mol­ecules which lead to the distinctive spikes in the corresponding decomposed fingerprint plots with a contribution of 26.4% for DTBA and 22.2% for 2CBA. Further delin­eation of the contact shows that DTBA possesses about 11.1% of (inter­nal)-H⋯O-(external) and 15.3% (inter­nal)-O⋯H-(external) compared to 2CBA with 10.9 and 11.2% of the equivalent contacts, both with approximately the same di + de contact distance of ∼1.70 Å for DTBA and ∼1.62 Å for 2CBA. Additional contacts for DTBA and 2CBA are respectively dominated by C⋯H/H⋯C (17.5%, di + de ∼2.18 Å; 14.8%, di + de ∼3.16 Å), S⋯H/H⋯S (12.3%, di + de ∼2.72 Å; 1.5%, di + de ∼3.38 Å) and Cl⋯H/H⋯Cl (2.8%, di + de ∼2.74 Å; 17.7%, di + de ∼2.74 Å). As for the DMF solvent mol­ecule, this exhibits a relatively different claw-like profile with several disproportional spikes observed in the fingerprint plot mainly owing to the asymmetric inter­action environment for the O⋯H/ H⋯O contact, in which the contribution of (inter­nal)-O⋯H-(external) contact to the Hirshfeld surfaces is about 14.6% (di + de ∼1.60 Å), while the (inter­nal)-H⋯O-(external) contact is about 11.2% (di + de ∼2.22 Å) that can be summed up to yield an overall 25.8%. The contribution of other short contacts is noted in decreasing order: H⋯H (47.4%, di + de ∼2.20 Å), C⋯H/ H⋯C (15.4%, di + de ∼2.90 Å) and H⋯S (4.4%, di + de ∼3.36 Å), respectively.

5. Computational chemistry study

The energy calculations through Crystal Explorer 17, Table 2[link], indicate that the strongest inter­action occurs between the hydrogen-bonded DTBA and 2CBA mol­ecules [DTBA-O—H⋯O(carbonyl-2CBA)/DTBA=O⋯H—O-(hydroxyl-2CBA)] dimer with an inter­action energy (Eint) of −73.2 kJ mol−1. This energy is about one and a half-fold greater than the second strongest inter­action that occurs between DTBA-DMF [DTBA-O—H⋯O(carbonyl-DMF)/ DTBA=O⋯H—C-(DMF)] with an Eint = −45.9 kJ mol−1. The disparity in energy is likely due the replacement of one O—H⋯O hydrogen bond with a C—H⋯O inter­action in the latter inter­action.

Table 2
Inter­action energies (kJ mol−1) for selected close contacts

Contact Eelectrostatic Epolarization Edispersion Eexchange-repulsion Etotal Symmetry operation
O2—H2⋯O3/O4—H4O⋯O1 −123.7 −28.0 −13.0 145.1 −73.2 x, y, z
O6—H6O⋯O7/C22—H22⋯O5 −82.4 −19.2 −11.4 105.7 −45.9 x, y, z
Cg1(C9/C14)⋯Cg2(C2/C7)/C6—H16⋯Cl1 −4.1 −1.7 −41.9 30.3 −23.4 1 − x, 1 − y, − z
Cg3(C1O1O2⋯C8O3O4)⋯Cg2(C2/C7) −1.0 −1.8 −30.7 21.6 −15.9 1 − x, − y, − z
C11—H11⋯S1/C11—H11⋯O3 −11.6 −2.2 −15.0 21.3 −13.8 −1 + x, y, z
C24—H24C⋯S2/C24—H24C⋯O5 −10.3 −2.5 −14.3 19.5 −13.2 1 − x, − y, 1 − z
C10—H10⋯O2/C3—H3⋯O4 −2.4 −1.1 −14.5 15.4 −6.5 −x, −y, 1 − z

On the other hand, the π–π inter­action between the hydrogen bond-mediated dimer of (DTBA)2 and the 2CBA-benzene ring gives an energy of −15.9 kJ mol−1 which is considered weak in nature. This indicates the energy is mainly dominated by dispersive forces, Table 2[link], which validates the previous finding on ESP mapping. Inter­estingly, a recent study demonstrated that the presence of external agents such as Lewis acids may either increase or decrease the strength of resonance assisted hydrogen bonds (RAHB) depending on the position of inter­action of the external agent with a carb­oxy­lic acid dimer (Grabowski, 2008[Grabowski, S. (2008). J. Phys. Org. Chem. 21, 694-702.]). The Eint for other inter­actions present in the crystal were also calculated and the results are summarized as in Table 2[link]. Generally, the energies for these inter­actions range between −23.4 to −6.5 kJ mol−1 which can be considered weak.

The energy frameworks of (I)[link] were also generated. The results of the calculations show that the mol­ecular packing is mainly governed by electrostatic forces which can be attributed to the strong O—H⋯O inter­actions, Fig. 5[link]. The inter­actions coupled with the near orthogonal arrangement of the two carb­oxy­lic acid moieties of DTBA lead to a discrete, directional V-shape electrostatic energy topology which is arranged in an alternate array along the c-axis direction. A relatively weaker dispersion force co-exists along with the main energy framework due to π–π inter­actions which help to sustain the overall mol­ecular packing of (I)[link].

[Figure 5]
Figure 5
Energy framework of (I)[link] as viewed down along the b axis, showing the energy framework comprising (a) electrostatic potential force, (b) dispersion force and (c) total energy. The cylindrical radii are proportional to the relative strength of the respective energies and they were scaled by a factor of 80 with a cut-off energy value of 5 kJ mol−1 within 4 × 4 × 4 unit cells.

A structural analogue of (I)[link] in the literature is the 2:1 co-crystal composed of two DTBA mol­ecules and the isomeric 3-chloro­benzoic acid (3CBA) mol­ecule, (II) (Tan & Tiekink, 2019b[Tan, S. L. & Tiekink, E. R. T. (2019b). Z. Kristallogr. New Cryst. Struct. 234 doi: 10.1515/ncrs-2018-0442.]). Unlike (I)[link], in which hydrogen bonds are formed between DTBA, 2CBA and DMF to result in a three-mol­ecule aggregate, Fig. 2[link](a), in (II) the two DTBA mol­ecules (DTBA-IIa and DTBA-IIb) form hydrogen bonds with each other, to yield a non-symmetric homosynthon, and with the two remaining carb­oxy­lic acid groups being hydrogen bonded to two 3CBA mol­ecules to give rise to a four-mol­ecule aggregate.

A mol­ecular cluster of (I)[link] and (II) containing 20 mol­ecules was subjected to mol­ecular packing analysis using Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]), with the geometric tolerances being set to the default values (20% for distance and 20° for angle tolerance); mol­ecular inversions were allowed during the comparison. The study shows that there are five pairs of DTBA mol­ecules from (I)[link] and (II) which exhibit close similarity in the mol­ecular packing with an r.m.s. deviation of 0.4 Å, Fig. 6[link].

[Figure 6]
Figure 6
A comparison of the mol­ecular packing between (I)[link] (blue) and (II) (red), showing the similarity between five pairs of DTBA mol­ecules with an overall r.m.s. deviation of 0.4 Å.

Both (I)[link] and (II) also exhibit similarity in terms of their close contacts as evidenced from the percentage contribution of the corresponding contacts obtained through Hirshfeld surface analysis for the DTBA mol­ecules in (I)[link] and (II), 2CBA in (I)[link] or 3CBA in (II), Fig. 7[link]. In general, the variations in contributions between those DTBA mol­ecules as well as 2CBA and 3CBA are relatively small: these differences range from 0.2 to 2.9% and 1.0 to 2.7% respectively. Exceptions are noted in the C⋯H/ H⋯C contacts which contribute about 17.5% of the overall contacts in DTBA-I, that is about 7.4 and 3.4% higher than the contacts in DTBA-IIa and DTBA-IIb, respectively. On the other hand, a relatively higher contribution is observed for the C⋯C contacts in 3CBA (ca 12.4%) which is approximately 6% greater than 2CBA in (I)[link] (ca 6.3%).

[Figure 7]
Figure 7
Percentage distribution of the corresponding close contacts to the Hirshfeld surfaces of (a) DTBA in (I)[link], (b) first DTBA mol­ecule in (II), (c) second DTBA mol­ecule in (II), (d) 2CBA in (I)[link] and (e) 3CBA in (II).

6. Database survey

There are over 200 structures included in the Cambridge Structural Database (version5.40; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) featuring hydrogen bonds between carb­oxy­lic acid residues and DMF. The most relevant structure is that of the 1:2 DTBA:DMF solvate (Cai et al., 2006[Cai, Y.-P., Sun, F., Zhu, L.-C., Yu, Q.-Y. & Liu, M.-S. (2006). Acta Cryst. E62, o841-o842.]). Here, both carb­oxy­lic acid residues engage in hydrogen bonding inter­actions with DMF mol­ecules akin to that seen in (I)[link]. There are approximately 250 structures where (non-coordinated) DMF and a carb­oxy­lic acid residue are present in the same crystal but no hydrogen bonding is evident between them. This suggest a 40% likelihood of hydrogen bonding between carb­oxy­lic acids and DMF, a percentage higher than for the formation of the eight-membered {⋯HOCO}2 synthon in carb­oxy­lic acid structures, i.e. 33%, emphasizing that this particular synthon can be readily disrupted in the presence of competing synthons (Allen et al., 1999[Allen, F. H., Motherwell, W. D. S., Raithby, P. R., Shields, G. P. & Taylor, R. (1999). New J. Chem. 23, 25-34.]).

7. Synthesis and crystallization

All chemical precursors were of reagent grade and used as received without further purification. 2-Mercapto­benzoic acid (Merck; 0.154 g, 0.001 mol) was mixed with 2-chloro­benzoic acid (Hopkin & Williams, 0.157 g, 0.001 mol) and ground for 15 mins in the presence of a few drops of methanol. The procedure was repeated three times. Colourless blocks were obtained through the careful layering of toluene (1 ml) on an N,N-di­methyl­formamide (1 ml) solution of the ground mixture. M.p. 437.3–438.9 K. IR (cm−1): 3076 ν(C—H), 1678 ν(C=O), 1473 ν(C=C), 1426 δ(C—H), 736 δ(C—Cl).

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. The carbon-bound H atoms were placed in calculated positions (C—H = 0.93–0.96 Å) and were included in the refinement in the riding-model approximation, with Uiso(H) set to 1.2–1.5Ueq(C). The oxygen-bound H atoms were located from difference Fourier maps and refined without constraint. Owing to poor agreement, one reflection, i.e. (4 2 2), was omitted from the final cycles of refinement.

Table 3
Experimental details

Crystal data
Chemical formula C14H10O4S2·C7H5ClO2·C3H7NO
Mr 536.00
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 7.7487 (3), 7.8575 (3), 21.4486 (6)
α, β, γ (°) 86.136 (3), 88.693 (2), 65.080 (4)
V (Å3) 1181.61 (8)
Z 2
Radiation type Cu Kα
μ (mm−1) 3.50
Crystal size (mm) 0.19 × 0.12 × 0.03
 
Data collection
Diffractometer XtaLAB Synergy, Dualflex, AtlasS2
Absorption correction Gaussian (CrysAlis PRO; Rigaku OD, 2018[Rigaku OD (2018). CrysAlis PRO Software system. Rigaku Oxford Diffraction, Oxford, UK.])
Tmin, Tmax 0.413, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 40239, 4915, 4507
Rint 0.057
(sin θ/λ)max (Å−1) 0.630
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.203, 1.10
No. of reflections 4915
No. of parameters 330
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 1.21, −0.83
Computer programs: CrysAlis PRO (Rigaku OD, 2018[Rigaku OD (2018). CrysAlis PRO Software system. Rigaku Oxford Diffraction, Oxford, UK.]), SHELXT (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. A71, 3-8.]), SHELXL (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC reference: 1903993

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S205698901900375X/hb7808sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901900375X/hb7808Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698901900375X/hb7808Isup3.cml

checkCIF report


Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL (Sheldrick, 2015a); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

2,2'-Dithiodibenzoic acid–2-chlorobenzoic acid–N,N-dimethylformamide (1/1/1) top
Crystal data top
C14H10O4S2·C7H5ClO2·C3H7NOZ = 2
Mr = 536.00F(000) = 556
Triclinic, P1Dx = 1.506 Mg m−3
a = 7.7487 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 7.8575 (3) ÅCell parameters from 21119 reflections
c = 21.4486 (6) Åθ = 4.0–76.1°
α = 86.136 (3)°µ = 3.50 mm−1
β = 88.693 (2)°T = 100 K
γ = 65.080 (4)°Plate, colourless
V = 1181.61 (8) Å30.19 × 0.12 × 0.03 mm
Data collection top
XtaLAB Synergy, Dualflex, AtlasS2
diffractometer		4915 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source4507 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.057
Detector resolution: 5.2558 pixels mm-1θmax = 76.1°, θmin = 4.1°
ω scansh = −9→9
Absorption correction: gaussian
(CrysAlisPro; Rigaku OD, 2018)		k = −9→9
Tmin = 0.413, Tmax = 1.000l = −24→26
40239 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.067H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.203 w = 1/[σ2(Fo2) + (0.1187P)2 + 2.0348P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
4915 reflectionsΔρmax = 1.21 e Å−3
330 parametersΔρmin = −0.83 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
xyzUiso*/Ueq
S10.59149 (11)0.53119 (12)0.76852 (4)0.0306 (2)
Cl10.45069 (12)0.95992 (13)1.14356 (4)0.0349 (2)
S20.59937 (12)0.53437 (12)0.67272 (4)0.0308 (2)
O40.3171 (4)0.6699 (4)0.95268 (11)0.0326 (5)
H4O0.364 (8)0.709 (7)0.973 (3)0.052 (15)*
O30.5740 (3)0.5927 (3)0.89192 (10)0.0296 (5)
O20.7735 (4)0.6833 (4)0.97404 (12)0.0354 (6)
H2O0.712 (8)0.652 (8)0.950 (3)0.060 (16)*
O10.5007 (3)0.7890 (4)1.02638 (11)0.0344 (6)
O50.6630 (4)0.5440 (4)0.55037 (12)0.0418 (6)
O60.8588 (4)0.3049 (4)0.49649 (12)0.0410 (6)
H6O0.841 (7)0.395 (7)0.468 (2)0.045 (13)*
O70.8389 (4)0.5600 (4)0.41008 (12)0.0434 (6)
N10.7396 (5)0.8751 (5)0.39798 (14)0.0400 (7)
C90.2951 (5)0.5828 (4)0.85135 (15)0.0267 (6)
C10.6657 (5)0.7680 (5)1.02109 (15)0.0275 (6)
C140.3607 (5)0.5473 (5)0.78952 (15)0.0270 (6)
C80.4089 (4)0.6141 (5)0.90013 (15)0.0267 (6)
C20.7656 (5)0.8312 (5)1.06648 (15)0.0280 (6)
C120.0633 (5)0.5400 (5)0.76228 (16)0.0306 (7)
H12−0.0162660.5262110.7318340.037*
C100.1132 (5)0.5965 (5)0.86691 (15)0.0291 (7)
H100.0681600.6221040.9083350.035*
C130.2422 (5)0.5262 (5)0.74536 (15)0.0295 (7)
H130.2845610.5023620.7036000.035*
C60.7871 (5)0.9609 (5)1.16394 (16)0.0323 (7)
H6A0.7301711.0152281.2016430.039*
C11−0.0011 (5)0.5736 (5)0.82314 (16)0.0318 (7)
H11−0.1231160.5806470.8344700.038*
C50.9736 (5)0.9304 (5)1.15083 (17)0.0345 (7)
H51.0441520.9630151.1796890.041*
C70.6831 (5)0.9126 (5)1.12226 (15)0.0274 (6)
C160.6785 (5)0.1584 (5)0.70069 (16)0.0338 (7)
H160.6264130.1960470.7406350.041*
C150.6826 (5)0.2925 (5)0.65578 (16)0.0312 (7)
C210.7543 (5)0.3771 (5)0.54597 (16)0.0336 (7)
C200.7578 (5)0.2356 (5)0.59629 (16)0.0330 (7)
C30.9540 (5)0.8034 (5)1.05434 (17)0.0319 (7)
H31.0122390.7495751.0167080.038*
C220.7667 (6)0.7194 (5)0.42990 (18)0.0413 (9)
H220.7276430.7287130.4723190.050*
C170.7494 (6)−0.0294 (5)0.68806 (18)0.0402 (8)
H170.743500−0.1190550.7190450.048*
C190.8321 (6)0.0448 (5)0.58490 (18)0.0398 (8)
H190.8857220.0052470.5452620.048*
C41.0573 (5)0.8524 (5)1.09581 (18)0.0368 (8)
H4A1.1846080.8326531.0865670.044*
C180.8290 (6)−0.0872 (5)0.63029 (19)0.0432 (9)
H180.880856−0.2165000.6220250.052*
C230.7881 (7)0.8803 (6)0.33196 (18)0.0441 (9)
H23A0.8542110.9620190.3245000.066*
H23B0.6714350.9294590.3066550.066*
H23C0.8710870.7529670.3203890.066*
C240.6454 (7)1.0572 (6)0.4254 (2)0.0487 (10)
H24A0.6262071.0375880.4701180.073*
H24B0.5218381.1297210.4048250.073*
H24C0.7248831.1263610.4194630.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0263 (4)0.0454 (5)0.0243 (4)−0.0182 (3)0.0065 (3)−0.0111 (3)
Cl10.0324 (4)0.0482 (5)0.0290 (4)−0.0208 (4)0.0096 (3)−0.0119 (3)
S20.0342 (4)0.0354 (4)0.0240 (4)−0.0152 (3)0.0080 (3)−0.0083 (3)
O40.0306 (12)0.0483 (14)0.0260 (12)−0.0220 (11)0.0055 (9)−0.0132 (10)
O30.0229 (11)0.0420 (13)0.0266 (11)−0.0153 (10)0.0053 (8)−0.0106 (9)
O20.0300 (12)0.0515 (15)0.0287 (12)−0.0195 (11)0.0069 (10)−0.0152 (11)
O10.0266 (12)0.0495 (15)0.0309 (12)−0.0180 (11)0.0065 (9)−0.0158 (10)
O50.0530 (16)0.0358 (14)0.0291 (13)−0.0115 (12)0.0136 (11)−0.0056 (10)
O60.0519 (16)0.0363 (13)0.0284 (13)−0.0123 (12)0.0155 (11)−0.0069 (11)
O70.0574 (17)0.0385 (14)0.0313 (13)−0.0169 (12)0.0120 (12)−0.0081 (11)
N10.0502 (19)0.0412 (17)0.0297 (15)−0.0200 (15)0.0053 (13)−0.0058 (13)
C90.0266 (15)0.0296 (15)0.0242 (15)−0.0117 (12)0.0016 (12)−0.0056 (12)
C10.0259 (15)0.0313 (16)0.0251 (15)−0.0113 (12)0.0035 (12)−0.0059 (12)
C140.0255 (15)0.0305 (15)0.0267 (15)−0.0127 (12)0.0046 (12)−0.0077 (12)
C80.0252 (15)0.0316 (16)0.0250 (15)−0.0131 (12)0.0034 (12)−0.0067 (12)
C20.0254 (15)0.0316 (16)0.0257 (15)−0.0105 (12)0.0019 (12)−0.0040 (12)
C120.0279 (16)0.0355 (17)0.0302 (16)−0.0141 (13)−0.0001 (13)−0.0082 (13)
C100.0280 (16)0.0349 (17)0.0262 (16)−0.0143 (13)0.0054 (12)−0.0082 (13)
C130.0278 (16)0.0372 (17)0.0242 (15)−0.0136 (13)0.0031 (12)−0.0080 (13)
C60.0353 (18)0.0357 (17)0.0248 (16)−0.0134 (14)−0.0001 (13)−0.0042 (13)
C110.0255 (16)0.0386 (18)0.0332 (17)−0.0145 (14)0.0034 (13)−0.0097 (14)
C50.0334 (18)0.0379 (18)0.0333 (18)−0.0152 (14)−0.0034 (14)−0.0062 (14)
C70.0269 (15)0.0302 (15)0.0250 (15)−0.0118 (12)0.0033 (12)−0.0042 (12)
C160.0318 (17)0.0385 (18)0.0274 (16)−0.0109 (14)0.0060 (13)−0.0057 (13)
C150.0268 (16)0.0368 (17)0.0273 (16)−0.0102 (13)0.0042 (12)−0.0076 (13)
C210.0359 (18)0.0390 (18)0.0255 (16)−0.0146 (15)0.0080 (13)−0.0095 (13)
C200.0335 (17)0.0372 (18)0.0264 (16)−0.0125 (14)0.0052 (13)−0.0062 (13)
C30.0259 (16)0.0387 (18)0.0331 (17)−0.0142 (14)0.0042 (13)−0.0125 (14)
C220.046 (2)0.040 (2)0.0353 (19)−0.0148 (17)0.0088 (16)−0.0088 (15)
C170.043 (2)0.0355 (18)0.0367 (19)−0.0116 (16)0.0097 (15)−0.0009 (15)
C190.044 (2)0.0384 (19)0.0321 (18)−0.0115 (16)0.0110 (15)−0.0099 (15)
C40.0259 (16)0.046 (2)0.0392 (19)−0.0151 (15)0.0014 (14)−0.0108 (16)
C180.052 (2)0.0323 (18)0.040 (2)−0.0119 (16)0.0109 (17)−0.0082 (15)
C230.060 (3)0.048 (2)0.0304 (18)−0.028 (2)0.0074 (17)−0.0047 (16)
C240.061 (3)0.038 (2)0.041 (2)−0.0153 (19)0.0057 (19)−0.0063 (17)
Geometric parameters (Å, º) top
S1—S22.0531 (11)C13—H130.9500
S1—C141.788 (3)C6—H6A0.9500
Cl1—C71.736 (3)C6—C51.387 (5)
S2—C151.791 (4)C6—C71.389 (5)
O4—H4O0.74 (6)C11—H110.9500
O4—C81.317 (4)C5—H50.9500
O3—C81.229 (4)C5—C41.384 (5)
O2—H2O0.82 (6)C16—H160.9500
O2—C11.320 (4)C16—C151.389 (5)
O1—C11.222 (4)C16—C171.384 (5)
O5—C211.209 (4)C15—C201.411 (5)
O6—H6O0.87 (5)C21—C201.488 (5)
O6—C211.326 (4)C20—C191.398 (5)
O7—C221.238 (5)C3—H30.9500
N1—C221.298 (5)C3—C41.385 (5)
N1—C231.459 (5)C22—H220.9500
N1—C241.463 (5)C17—H170.9500
C9—C141.412 (4)C17—C181.388 (5)
C9—C81.480 (4)C19—H190.9500
C9—C101.402 (5)C19—C181.381 (6)
C1—C21.489 (5)C4—H4A0.9500
C14—C131.398 (5)C18—H180.9500
C2—C71.404 (4)C23—H23A0.9800
C2—C31.403 (5)C23—H23B0.9800
C12—H120.9500C23—H23C0.9800
C12—C131.386 (5)C24—H24A0.9800
C12—C111.389 (5)C24—H24B0.9800
C10—H100.9500C24—H24C0.9800
C10—C111.376 (5)
C14—S1—S2105.47 (11)C6—C7—C2120.5 (3)
C15—S2—S1104.62 (12)C15—C16—H16119.5
C8—O4—H4O113 (4)C17—C16—H16119.5
C1—O2—H2O110 (4)C17—C16—C15120.9 (3)
C21—O6—H6O109 (3)C16—C15—S2121.2 (3)
C22—N1—C23122.3 (3)C16—C15—C20119.1 (3)
C22—N1—C24121.4 (3)C20—C15—S2119.7 (3)
C23—N1—C24116.1 (3)O5—C21—O6123.2 (3)
C14—C9—C8122.3 (3)O5—C21—C20122.2 (3)
C10—C9—C14119.3 (3)O6—C21—C20114.6 (3)
C10—C9—C8118.4 (3)C15—C20—C21120.5 (3)
O2—C1—C2113.6 (3)C19—C20—C15119.0 (3)
O1—C1—O2122.2 (3)C19—C20—C21120.5 (3)
O1—C1—C2124.2 (3)C2—C3—H3119.2
C9—C14—S1120.0 (2)C4—C3—C2121.7 (3)
C13—C14—S1120.9 (2)C4—C3—H3119.2
C13—C14—C9119.0 (3)O7—C22—N1125.9 (4)
O4—C8—C9114.4 (3)O7—C22—H22117.0
O3—C8—O4122.8 (3)N1—C22—H22117.0
O3—C8—C9122.8 (3)C16—C17—H17119.9
C7—C2—C1123.4 (3)C16—C17—C18120.2 (3)
C3—C2—C1118.8 (3)C18—C17—H17119.9
C3—C2—C7117.8 (3)C20—C19—H19119.4
C13—C12—H12119.6C18—C19—C20121.1 (3)
C13—C12—C11120.9 (3)C18—C19—H19119.4
C11—C12—H12119.6C5—C4—C3119.5 (3)
C9—C10—H10119.5C5—C4—H4A120.3
C11—C10—C9121.1 (3)C3—C4—H4A120.3
C11—C10—H10119.5C17—C18—H18120.2
C14—C13—H13119.9C19—C18—C17119.5 (4)
C12—C13—C14120.3 (3)C19—C18—H18120.2
C12—C13—H13119.9N1—C23—H23A109.5
C5—C6—H6A119.8N1—C23—H23B109.5
C5—C6—C7120.4 (3)N1—C23—H23C109.5
C7—C6—H6A119.8H23A—C23—H23B109.5
C12—C11—H11120.3H23A—C23—H23C109.5
C10—C11—C12119.4 (3)H23B—C23—H23C109.5
C10—C11—H11120.3N1—C24—H24A109.5
C6—C5—H5119.9N1—C24—H24B109.5
C4—C5—C6120.2 (3)N1—C24—H24C109.5
C4—C5—H5119.9H24A—C24—H24B109.5
C2—C7—Cl1123.5 (3)H24A—C24—H24C109.5
C6—C7—Cl1116.0 (3)H24B—C24—H24C109.5
S1—S2—C15—C1617.0 (3)C2—C3—C4—C50.2 (6)
S1—S2—C15—C20−161.5 (3)C10—C9—C14—S1179.5 (3)
S1—C14—C13—C12−179.7 (3)C10—C9—C14—C13−0.2 (5)
S2—S1—C14—C9−168.5 (2)C10—C9—C8—O4−6.1 (4)
S2—S1—C14—C1311.1 (3)C10—C9—C8—O3175.0 (3)
S2—C15—C20—C21−4.9 (5)C13—C12—C11—C101.1 (5)
S2—C15—C20—C19176.4 (3)C6—C5—C4—C3−0.7 (6)
O2—C1—C2—C7−175.4 (3)C11—C12—C13—C14−0.4 (5)
O2—C1—C2—C32.5 (5)C5—C6—C7—Cl1−179.4 (3)
O1—C1—C2—C73.7 (5)C5—C6—C7—C20.3 (5)
O1—C1—C2—C3−178.3 (3)C7—C2—C3—C40.5 (5)
O5—C21—C20—C15−11.7 (6)C7—C6—C5—C40.4 (6)
O5—C21—C20—C19167.0 (4)C16—C15—C20—C21176.5 (3)
O6—C21—C20—C15168.3 (3)C16—C15—C20—C19−2.1 (5)
O6—C21—C20—C19−13.0 (5)C16—C17—C18—C19−1.8 (7)
C9—C14—C13—C120.0 (5)C15—C16—C17—C181.1 (6)
C9—C10—C11—C12−1.3 (5)C15—C20—C19—C181.5 (6)
C1—C2—C7—Cl1−3.2 (5)C21—C20—C19—C18−177.2 (4)
C1—C2—C7—C6177.1 (3)C20—C19—C18—C170.5 (7)
C1—C2—C3—C4−177.5 (3)C3—C2—C7—Cl1178.9 (3)
C14—C9—C8—O4171.4 (3)C3—C2—C7—C6−0.8 (5)
C14—C9—C8—O3−7.5 (5)C17—C16—C15—S2−177.6 (3)
C14—C9—C10—C110.8 (5)C17—C16—C15—C200.9 (5)
C8—C9—C14—S12.1 (4)C23—N1—C22—O71.9 (7)
C8—C9—C14—C13−177.6 (3)C24—N1—C22—O7177.4 (4)
C8—C9—C10—C11178.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O30.83 (6)1.86 (7)2.687 (4)176 (9)
O4—H4O···O10.73 (7)1.88 (6)2.612 (4)175 (5)
O6—H6O···O70.87 (5)1.73 (5)2.594 (4)172 (5)
C3—H3···O4i0.952.573.363 (5)142
C10—H10···O2ii0.952.543.331 (5)141
C11—H11···S1ii0.952.833.544 (4)133
C22—H22···O50.952.333.095 (5)138
C24—H24B···S2iii0.982.833.531 (4)129
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) −x+1, −y, −z+1.
Interaction energies (kJ mol-1) for selected close contacts top
ContactEelectrostaticEpolarizationEdispersionEexchange-repulsionEtotalSymmetry operation
O2—H2···O3/O4—H4O···O1-123.7-28.0-13.0145.1-73.2x, y, z
O6—H6O···O7/C22—H22···O5-82.4-19.2-11.4105.7-45.9x, y, z
Cg1(C9/C14)···Cg2(C2/C7)/C6—H16···Cl1-4.1-1.7-41.930.3-23.41 - x, 1 - y, - z
Cg3(C1O1O2···C8O3O4)···Cg2(C2/C7)-1.0-1.8-30.721.6-15.91 - x, - y, - z
C11—H11···S1/ C11—H11···O3-11.6-2.2-15.021.3-13.8-1 + x, y, z
C24—H24C···S2/ C24—H24C···O5-10.3-2.5-14.319.5-13.21 - x, - y, 1 - z
C10—H10···O2/ C3—H3···O4-2.4-1.1-14.515.4-6.5-x, -y, 1 - z
 

Funding information

The support of Sunway University for studies in co-crystals, through Grant No. INT-FST-RCCM-2016–01, is gratefully acknowledged.

References

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ISSN: 2056-9890
Volume 75| Part 4| April 2019| Pages 475-481
https://doi.org/10.1107/S205698901900375X
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