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Logo of actae2this articlesearchopen accesssubmitActa Crystallographica Section E: Crystallographic CommunicationsActa Crystallographica Section E: Crystallographic Communications
 
Acta Crystallogr E Crystallogr Commun. 2017 October 1; 73(Pt 10): 1483–1487.
Published online 2017 September 15. doi:  10.1107/S2056989017012981
PMCID: PMC5730300

Crystal structures of 2-methyl­pyridinium hydrogen 2,3-bis­(4-methyl­benzo­yloxy)succinate and bis-[4-methyl­pyridinium hydrogen 2,3-bis­(4-methyl­benzo­yloxy)succinate] penta­hydrate

Abstract

The title salt (I), C6H8N+·C20H17O8 , comprises a 2-methyl­pyridinium cation and a 2,3-bis­(4-methyl­benzo­yloxy)succinate mono-anion while the salt (II), 2C6H8N+·2C20H17O8 ·5H2O, consists of a pair of 4-methyl­pyridinium cations and 2,3-bis­(4-methyl­benzo­yloxy)succinate mono-anions and five water mol­ecules of solvation in the asymmetric unit. In (I), the dihedral angle between the aromatic rings of the anion is 40.41 (15)°, comparing with 43.0 (3) and 85.7 (2)° in the conformationally dissimilar anion mol­ecules in (II). The pyridine ring of the cation in (I) is inclined at 23.64 (16) and 42.69 (17)° to the two benzene moieties of the anion. In (II), these comparative values are 4.7 (3), 43.5 (3)° and 43.5 (3), 73.1 (3)° for the two associated cation and anion pairs. The crystal packing of (I) is stabilized by inter-ionic N—H(...)O, O—H(...)O and C—H(...)O hydrogen bonds as well as weak C—H(...)π inter­actions, linking the ions into infinite chains along [100]. In the crystal packing of (II), the anions and cations are also linked by N—H(...)O and O—H(...)O hydrogen bonds involving also the water mol­ecules, giving a two-dimensional network across (001). The crystal structure is also stabilized by weak C—H(...)O and C—H(...)π inter­actions.

Keywords: succinates, pyridinium salts, hydrogen bonding, crystal structure

Chemical context  

Pyridine derivatives exhibit biological activities such as anti­viral (Hamdouchi et al., 1999  ), anti­bacterial (Rival et al., 1992  ), anti­microbial (Jo et al., 2004  ), anti­thrombotic (Sunkel et al., 1990  ). Some pyridine derivatives possess non-linear optical (NLO) properties (Tomaru et al., 1991  ) and often possess anti­bacterial and anti­fungal activities (Akkurt et al., 2005  ). We have now synthesized and determined the crystal structures of the title 1:1 salts of the chiral diprotic acid, 2,3-bis­(4-methyl­benzo­yloxy)succinic acid with 2-methyl­pyridine, C6H8N+·C20H17O8 , (I), and with 4-methyl­pyridine, 2C6H8N+·2C20H17O8 ·5H2O, (II).

Structural commentary  

In both the salts of 2,3-bis­(4-methyl­benzo­yloxy)succinic acid [(I) and (II), Figs. 1  and 2  , respectively], the N atoms of the pyridine mol­ecules are protonated. With (I), the asymmetric unit comprises a single 2-methyl­pyridinium cation and a succinate mono-anion (Fig. 1  ) whereas with (II), the asymmetric unit comprises two 4-methyl­pyridinium cations and two succinate mono-anions along with five water mol­ecules of solvation (Fig. 2  ). In salt (I), the dihedral angle between the aromatic rings (C2–C7) and (C14–C19) is 40.41 (15)°. The pyridine ring (N1/C22–C26) is inclined at angles of 23.64 (16) and 42.69 (17)° with the benzene rings (C2–C7) and (C14–C19), respectively. In salt (II), the benzene ring (C2–C7) forms a dihedral angle of 43.0 (3)° with the benzene ring (C14–C19) whereas the benzene ring (C40–C45) and (C28–C33) are inclined at an angle of 85.7 (2)°. The dihedral angles between the pyridine ring (C22/C23/C24/N1/C25/C26) and the benzene rings (C2–C7) and (C14–C19) are 43.5 (3) and 4.7 (3)°, respectively, and those between the pyridine ring (C48/C49/C50/N2/C51/C52) and the benzene rings (C28–C33) and (C40–C45) are 73.1 (3) and 43.5 (3)°, respectively.

An external file that holds a picture, illustration, etc.
Object name is e-73-01483-scheme1.jpg

Figure 1
The mol­ecular structure and atom numbering scheme in the title salt (I), with 30% probability displacement ellipsoids. The inter-species hydrogen bond is shown as a dashed line.
Figure 2
The mol­ecular structure of the two independent cation and anion pairs and the water mol­ecules of solvation in the asymmetric unit of the title salt (II), with 30% probability displacement ellipsoids. Inter-species hydrogen bonds are ...

Supra­molecular features  

The crystal structure of (I) is stabilized by intra-ionic N—H(...)O, inter-ionic O—H(...)O, C—H(...)O (Table 1  , Fig. 3  ) and C—H(...)π (Table 1  ) inter­actions. The inter-ionic O—H(...)O hydrogen bond links the ions into an infinite chain along [100]. In the crystal packing of (II), the cations and anions are linked by N—H(...)O and O—H(...)O hydrogen bonds (Table 2  , Fig. 4  ), through water mol­ecules, giving an infinite two-dimensional network parallel to (001). The structure is further influenced by weak C—H(...)O hydrogen-bonding inter­actions and weak C—H(...)π contacts (Table 2  ) while there are also very weak π–π inter­actions between like pyridine rings [minimum ring-centroid separations Cg1(...)Cg6i, 3.996 (4) Å and Cg2(...)Cg5ii, 3.900 (3) Å where Cg1, Cg2, Cg5 and Cg6 are the centroids of the C2–C7, C14–C19, N1/C22–C26 and N2/C48–C52 rings, respectively; symmetry codes: (i) 1 + x, 1 + y, −1 + z; (ii) x, y, z].

Figure 3
The crystal packing of the title salt (I) in the unit cell, viewed along the a axis. The hydrogen bonds are shown as dashed lines and H atoms not involved in hydrogen bonding have been omitted.
Figure 4
The crystal packing of the title salt (II) in the unit cell, viewed along the b axis. The hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
Table 1
Hydrogen-bond geometry (Å, °) for (I)
Table 2
Hydrogen-bond geometry (Å, °) for (II)

Database survey  

The geometric parameters of the cation of (I), which contains 2-methyl pyridinium, are comparable with the reported crystal sructures of 2-methyl­pyridinium 2-carb­oxy­benzoate-benzene-1,2-di­carb­oxy­lic acid (2/1) (Sivakumar, Sudhahar, Gunasekaran et al., 2016  ); 2-methyl­pyridinium 2-carb­oxy-6-nitro­benzoate (Sivakumar, Sudhahar Israel et al., 2016  ); 2-methyl­pyridinium 5-(2,4-di­nitro­phen­yl)-1,3-di­methyl­barbiturate (Sridevi & Kalaivani, 2012  ). The geometric parameters of the 4-methyl­pyridinium cation of (II) are comparable with those reported in the crystal structures of 4-methyl­pyridinium 2-carb­oxy-6-nitro­benzoate (Devi et al., 2016  ), 4-methyl­pyridinium 4-hy­droxy­benzoate (Sudhahar et al., 2013  ) and 4-methyl­pyridinium 2-carb­oxy-4,5-di­chloro­benzoate monohydrate (Smith & Wermuth, 2010  ). The geometric parameters of anions of (I) and (II) are comparable with the reported structures of 2,3-di-p-tolyl-(2R,3R)-tartaric acid ethyl acetate solvate (Tang et al., 2006  ) and di-p-tolyl­tartaric acid with aromatic amines (Nassimbeni & Su, 2006  ).

Synthesis and crystallization  

The title salts (I) and (II) were synthesized using the reaction of equi-molar qu­anti­ties of di-p-tolyl-l-tartaric acid (0.967 g) and 0.237 g of either 2-methyl­pyridine [for (I)] or 4-methyl­pyridine [for (II)], dissolved in 10 ml of acetone. A white precipitate was formed, which was dissolved in 30 ml of water and then kept at room temperature for slow evaporation. After 2 months, crystals of (I) or (II), suitable for X-ray diffraction analysis were obtained.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 3  . C-bound H atoms were placed in calculated positions and allowed to ride on their carrier atoms, with C—H = 0.93 Å (aromatic CH), 0.98 Å for CH, or 0.96 Å (methyl CH), and with U iso = 1.5U eq(methyl C or O) and U iso = 1.2U eq(aromatic and methyl­ene C). H atoms for NH and OH groups were located in difference-Fourier maps and refined with a distance restraint [N—H = 0.86 (1) Å or O—H = 0.82 (1) Å]. The Flack absolute structure obtained for both structures (Parsons et al., 2013  ) for the arbitrarily numbered chiral atoms [C9R,C11R] gave ambiguous Flack parameters of 0.4 (4) [(for (I)] and 0.6 (3) [for (II)], for 1335 and 2690 quotients, respectively.

Table 3
Experimental details

Supplementary Material

Crystal structure: contains datablock(s) I, II, global. DOI: 10.1107/S2056989017012981/zs2388sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017012981/zs2388Isup2.hkl

Structure factors: contains datablock(s) II. DOI: 10.1107/S2056989017012981/zs2388IIsup3.hkl

CCDC references: 1573939, 1573938

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors wish to acknowledge the IIT, Madras, for the data collection.

supplementary crystallographic information

2-Methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate (I)   Crystal data

C20H17O8+·C6H8NDx = 1.306 Mg m3
Mr = 479.47Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 5788 reflections
a = 7.4849 (2) Åθ = 2.3–24.3°
b = 16.2063 (4) ŵ = 0.10 mm1
c = 20.0959 (7) ÅT = 296 K
V = 2437.68 (12) Å3Block, colourless
Z = 40.30 × 0.26 × 0.24 mm
F(000) = 1008

2-Methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate (I)   Data collection

Bruker APEXII CCD Diffractometer4206 reflections with I > 2σ(I)
ω and [var phi] scansRint = 0.038
Absorption correction: multi-scan (SADABS; Bruker, 2004)θmax = 30.3°, θmin = 2.4°
Tmin = 0.707, Tmax = 0.746h = −10→10
23766 measured reflectionsk = −21→22
7045 independent reflectionsl = −27→28

2-Methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate (I)   Refinement

Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.053w = 1/[σ2(Fo2) + (0.0586P)2 + 0.0095P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.124(Δ/σ)max < 0.001
S = 1.01Δρmax = 0.20 e Å3
7045 reflectionsΔρmin = −0.22 e Å3
326 parametersAbsolute structure: Flack x determined using 1335 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013).
2 restraintsAbsolute structure parameter: 0.4 (4)

2-Methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate (I)   Special details

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.

2-Methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate (I)   Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C20.6147 (4)0.14980 (19)0.02329 (15)0.0504 (7)
C30.5336 (4)0.13935 (17)0.08445 (15)0.0486 (7)
H30.4921290.0873320.0964140.058*
C40.5128 (4)0.20389 (16)0.12799 (15)0.0429 (7)
H40.4575600.1953860.1688720.051*
C50.5740 (4)0.28162 (15)0.11098 (14)0.0395 (6)
C60.6610 (4)0.29218 (18)0.05099 (16)0.0512 (8)
H60.7071420.3436240.0397630.061*
C70.6797 (4)0.22748 (19)0.00812 (17)0.0571 (9)
H70.7374570.235793−0.0322920.069*
C10.6274 (6)0.0795 (2)−0.02603 (19)0.0760 (11)
H1A0.5773600.030495−0.0067070.114*
H1B0.7505080.069861−0.0370160.114*
H1C0.5625190.093486−0.0656510.114*
C80.5389 (4)0.35568 (16)0.15234 (15)0.0435 (7)
C90.3662 (3)0.40446 (15)0.24351 (14)0.0359 (6)
H90.3867960.4558320.2189590.043*
C100.1651 (3)0.38826 (16)0.24566 (16)0.0413 (7)
C110.4517 (3)0.41223 (13)0.31095 (14)0.0328 (6)
H110.3873180.4541920.3366110.039*
C120.6476 (3)0.43854 (15)0.30436 (14)0.0384 (6)
C130.4645 (3)0.33626 (15)0.40973 (14)0.0378 (6)
C140.4553 (3)0.25329 (14)0.44002 (14)0.0363 (6)
C150.4030 (4)0.18421 (17)0.40542 (16)0.0494 (7)
H150.3722080.1884370.3607080.059*
C160.3961 (5)0.10887 (17)0.43680 (17)0.0558 (9)
H160.3602450.0626170.4128860.067*
C170.4412 (4)0.10048 (16)0.50286 (17)0.0519 (8)
C180.4951 (5)0.17001 (18)0.53717 (16)0.0567 (8)
H180.5256120.1658610.5819000.068*
C190.5040 (5)0.24497 (18)0.50593 (17)0.0504 (7)
H190.5433690.2909190.5294410.060*
C200.4279 (6)0.01852 (18)0.53753 (19)0.0741 (11)
H20A0.5169370.0153970.5718170.111*
H20B0.446815−0.0250360.5059370.111*
H20C0.3113810.0128610.5569940.111*
C260.9766 (5)0.56457 (19)0.1769 (2)0.0700 (10)
H260.9184520.5193930.1583390.084*
C251.0947 (7)0.6084 (2)0.1398 (2)0.0863 (13)
H251.1210290.5932440.0962610.104*
C241.1741 (5)0.6759 (2)0.1688 (3)0.0831 (13)
H241.2518310.7083920.1439930.100*
C231.1402 (5)0.6956 (2)0.2335 (2)0.0695 (11)
H231.1962230.7409060.2528660.083*
C221.0225 (4)0.64833 (17)0.27049 (17)0.0510 (8)
C210.9800 (5)0.6634 (2)0.34083 (19)0.0748 (11)
H21A0.9441560.7198250.3465230.112*
H21B1.0836260.6525510.3675860.112*
H21C0.8844020.6276220.3543480.112*
N10.9432 (3)0.58574 (14)0.23975 (15)0.0499 (6)
O10.5866 (4)0.42423 (12)0.13919 (13)0.0834 (9)
O20.4435 (2)0.33775 (10)0.20649 (9)0.0408 (4)
O30.0897 (3)0.35352 (16)0.20132 (14)0.0797 (8)
O40.0887 (2)0.41986 (12)0.29719 (12)0.0515 (5)
O50.6695 (3)0.51344 (11)0.29317 (12)0.0581 (6)
O60.7639 (2)0.38471 (11)0.30924 (12)0.0538 (6)
O70.4337 (2)0.33449 (9)0.34376 (9)0.0355 (4)
O80.4950 (3)0.39923 (11)0.43943 (11)0.0577 (6)
H10.864 (4)0.5548 (17)0.2594 (16)0.071 (11)*
H4A−0.021 (2)0.409 (2)0.299 (2)0.107*

2-Methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate (I)   Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C20.0479 (17)0.0592 (17)0.0441 (19)0.0101 (14)0.0032 (14)0.0005 (14)
C30.0537 (18)0.0465 (15)0.0457 (19)0.0005 (14)0.0045 (14)0.0050 (13)
C40.0412 (15)0.0513 (15)0.0363 (17)0.0006 (12)0.0077 (12)0.0094 (12)
C50.0338 (14)0.0470 (14)0.0378 (16)0.0035 (12)0.0073 (12)0.0090 (12)
C60.0514 (18)0.0523 (17)0.050 (2)0.0021 (14)0.0194 (16)0.0137 (14)
C70.059 (2)0.069 (2)0.043 (2)0.0081 (16)0.0214 (16)0.0100 (16)
C10.096 (3)0.075 (2)0.057 (2)0.014 (2)0.010 (2)−0.0102 (18)
C80.0385 (15)0.0482 (15)0.0438 (18)−0.0018 (13)0.0085 (13)0.0097 (13)
C90.0275 (12)0.0334 (13)0.0468 (17)0.0004 (10)0.0061 (11)0.0017 (11)
C100.0291 (13)0.0449 (15)0.0497 (19)−0.0054 (11)0.0003 (13)0.0040 (14)
C110.0215 (11)0.0283 (11)0.0485 (17)−0.0016 (9)0.0050 (11)0.0008 (11)
C120.0226 (12)0.0440 (15)0.0488 (18)−0.0063 (11)0.0030 (12)−0.0051 (12)
C130.0296 (13)0.0415 (14)0.0423 (17)−0.0023 (11)0.0030 (12)−0.0042 (12)
C140.0302 (13)0.0381 (13)0.0404 (17)−0.0025 (10)0.0052 (12)−0.0034 (11)
C150.061 (2)0.0454 (15)0.0419 (18)−0.0050 (14)−0.0013 (14)−0.0038 (14)
C160.070 (2)0.0403 (16)0.057 (2)−0.0068 (14)0.0044 (17)−0.0072 (15)
C170.0524 (17)0.0456 (16)0.058 (2)0.0025 (14)0.0096 (16)0.0052 (14)
C180.069 (2)0.0575 (18)0.0432 (19)−0.0056 (16)−0.0026 (15)0.0055 (15)
C190.0593 (19)0.0465 (15)0.0452 (19)−0.0059 (13)−0.0071 (15)−0.0057 (13)
C200.094 (3)0.0509 (18)0.077 (3)0.0023 (19)0.016 (2)0.0117 (17)
C260.085 (3)0.0507 (18)0.074 (3)0.0018 (18)−0.005 (2)0.0013 (17)
C250.108 (4)0.072 (2)0.079 (3)0.017 (2)0.031 (3)0.015 (2)
C240.065 (2)0.079 (3)0.105 (4)−0.008 (2)0.031 (2)0.027 (3)
C230.0501 (19)0.061 (2)0.097 (3)−0.0210 (16)0.002 (2)0.015 (2)
C220.0379 (15)0.0450 (16)0.070 (2)−0.0063 (13)−0.0037 (14)0.0135 (15)
C210.081 (3)0.078 (2)0.065 (3)−0.012 (2)−0.002 (2)0.010 (2)
N10.0405 (13)0.0422 (14)0.067 (2)−0.0073 (11)−0.0005 (13)0.0134 (12)
O10.117 (2)0.0464 (12)0.087 (2)−0.0150 (13)0.0531 (17)0.0060 (12)
O20.0408 (10)0.0384 (9)0.0432 (11)−0.0002 (8)0.0126 (9)0.0042 (8)
O30.0473 (12)0.1178 (19)0.0741 (18)−0.0229 (13)−0.0025 (12)−0.0307 (16)
O40.0229 (9)0.0668 (12)0.0649 (15)−0.0003 (9)0.0041 (10)−0.0068 (11)
O50.0414 (11)0.0413 (11)0.0916 (18)−0.0156 (9)0.0093 (11)0.0040 (10)
O60.0197 (8)0.0532 (11)0.0886 (17)0.0014 (8)0.0088 (10)0.0003 (11)
O70.0316 (9)0.0338 (9)0.0412 (11)−0.0055 (7)0.0030 (8)0.0000 (8)
O80.0778 (16)0.0406 (10)0.0546 (14)−0.0097 (10)−0.0055 (12)−0.0098 (9)

2-Methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate (I)   Geometric parameters (Å, º)

C2—C31.381 (4)C14—C151.375 (4)
C2—C71.383 (4)C14—C191.380 (4)
C2—C11.513 (4)C15—C161.375 (4)
C3—C41.373 (4)C15—H150.9300
C3—H30.9300C16—C171.376 (4)
C4—C51.383 (4)C16—H160.9300
C4—H40.9300C17—C181.381 (4)
C5—C61.381 (4)C17—C201.503 (4)
C5—C81.484 (4)C18—C191.369 (4)
C6—C71.364 (5)C18—H180.9300
C6—H60.9300C19—H190.9300
C7—H70.9300C20—H20A0.9600
C1—H1A0.9600C20—H20B0.9600
C1—H1B0.9600C20—H20C0.9600
C1—H1C0.9600C26—N11.332 (5)
C8—O11.196 (3)C26—C251.357 (6)
C8—O21.333 (3)C26—H260.9300
C9—O21.435 (3)C25—C241.374 (6)
C9—C111.504 (4)C25—H250.9300
C9—C101.528 (4)C24—C231.364 (6)
C9—H90.9800C24—H240.9300
C10—O31.196 (3)C23—C221.384 (4)
C10—O41.289 (4)C23—H230.9300
C11—O71.428 (3)C22—N11.328 (4)
C11—C121.533 (3)C22—C211.469 (5)
C11—H110.9800C21—H21A0.9600
C12—O61.237 (3)C21—H21B0.9600
C12—O51.245 (3)C21—H21C0.9600
C13—O81.204 (3)N1—H10.873 (13)
C13—O71.346 (3)O4—H4A0.839 (13)
C13—C141.478 (4)
C3—C2—C7117.5 (3)C19—C14—C13118.2 (2)
C3—C2—C1121.2 (3)C14—C15—C16120.1 (3)
C7—C2—C1121.3 (3)C14—C15—H15119.9
C4—C3—C2121.6 (3)C16—C15—H15119.9
C4—C3—H3119.2C15—C16—C17121.4 (3)
C2—C3—H3119.2C15—C16—H16119.3
C3—C4—C5119.9 (3)C17—C16—H16119.3
C3—C4—H4120.0C16—C17—C18118.2 (3)
C5—C4—H4120.0C16—C17—C20121.2 (3)
C6—C5—C4119.0 (3)C18—C17—C20120.6 (3)
C6—C5—C8118.2 (2)C19—C18—C17120.6 (3)
C4—C5—C8122.6 (2)C19—C18—H18119.7
C7—C6—C5120.3 (3)C17—C18—H18119.7
C7—C6—H6119.9C18—C19—C14120.9 (3)
C5—C6—H6119.9C18—C19—H19119.5
C6—C7—C2121.6 (3)C14—C19—H19119.5
C6—C7—H7119.2C17—C20—H20A109.5
C2—C7—H7119.2C17—C20—H20B109.5
C2—C1—H1A109.5H20A—C20—H20B109.5
C2—C1—H1B109.5C17—C20—H20C109.5
H1A—C1—H1B109.5H20A—C20—H20C109.5
C2—C1—H1C109.5H20B—C20—H20C109.5
H1A—C1—H1C109.5N1—C26—C25120.5 (4)
H1B—C1—H1C109.5N1—C26—H26119.7
O1—C8—O2122.8 (3)C25—C26—H26119.7
O1—C8—C5125.1 (3)C26—C25—C24117.7 (4)
O2—C8—C5112.1 (2)C26—C25—H25121.1
O2—C9—C11111.0 (2)C24—C25—H25121.1
O2—C9—C10106.4 (2)C23—C24—C25120.7 (4)
C11—C9—C10114.1 (2)C23—C24—H24119.6
O2—C9—H9108.4C25—C24—H24119.6
C11—C9—H9108.4C24—C23—C22120.0 (4)
C10—C9—H9108.4C24—C23—H23120.0
O3—C10—O4125.2 (3)C22—C23—H23120.0
O3—C10—C9121.6 (3)N1—C22—C23117.3 (3)
O4—C10—C9113.0 (2)N1—C22—C21118.5 (3)
O7—C11—C9107.58 (18)C23—C22—C21124.2 (3)
O7—C11—C12112.05 (19)C22—C21—H21A109.5
C9—C11—C12110.6 (2)C22—C21—H21B109.5
O7—C11—H11108.8H21A—C21—H21B109.5
C9—C11—H11108.8C22—C21—H21C109.5
C12—C11—H11108.8H21A—C21—H21C109.5
O6—C12—O5127.5 (2)H21B—C21—H21C109.5
O6—C12—C11118.1 (2)C22—N1—C26123.6 (3)
O5—C12—C11114.4 (2)C22—N1—H1122 (2)
O8—C13—O7122.6 (2)C26—N1—H1114 (2)
O8—C13—C14125.2 (3)C8—O2—C9118.4 (2)
O7—C13—C14112.2 (2)C10—O4—H4A113 (3)
C15—C14—C19118.7 (3)C13—O7—C11114.83 (19)
C15—C14—C13123.1 (3)
C7—C2—C3—C42.0 (5)O8—C13—C14—C19−7.5 (4)
C1—C2—C3—C4−176.4 (3)O7—C13—C14—C19172.8 (2)
C2—C3—C4—C5−0.1 (5)C19—C14—C15—C161.4 (4)
C3—C4—C5—C6−2.2 (4)C13—C14—C15—C16−179.5 (3)
C3—C4—C5—C8173.3 (3)C14—C15—C16—C17−0.2 (5)
C4—C5—C6—C72.6 (5)C15—C16—C17—C18−0.4 (5)
C8—C5—C6—C7−173.1 (3)C15—C16—C17—C20178.0 (3)
C5—C6—C7—C2−0.7 (5)C16—C17—C18—C19−0.3 (5)
C3—C2—C7—C6−1.6 (5)C20—C17—C18—C19−178.8 (3)
C1—C2—C7—C6176.8 (3)C17—C18—C19—C141.6 (5)
C6—C5—C8—O1−3.3 (5)C15—C14—C19—C18−2.1 (5)
C4—C5—C8—O1−178.8 (3)C13—C14—C19—C18178.8 (3)
C6—C5—C8—O2175.6 (3)N1—C26—C25—C24−1.6 (6)
C4—C5—C8—O20.1 (4)C26—C25—C24—C232.7 (6)
O2—C9—C10—O3−31.1 (4)C25—C24—C23—C22−1.1 (6)
C11—C9—C10—O3−153.9 (3)C24—C23—C22—N1−1.7 (5)
O2—C9—C10—O4152.7 (2)C24—C23—C22—C21178.6 (4)
C11—C9—C10—O430.0 (3)C23—C22—N1—C262.9 (4)
O2—C9—C11—O7−56.2 (2)C21—C22—N1—C26−177.4 (3)
C10—C9—C11—O764.1 (3)C25—C26—N1—C22−1.2 (5)
O2—C9—C11—C1266.5 (2)O1—C8—O2—C912.3 (4)
C10—C9—C11—C12−173.2 (2)C5—C8—O2—C9−166.7 (2)
O7—C11—C12—O619.8 (4)C11—C9—O2—C8−112.8 (2)
C9—C11—C12—O6−100.2 (3)C10—C9—O2—C8122.5 (2)
O7—C11—C12—O5−161.5 (2)O8—C13—O7—C114.0 (4)
C9—C11—C12—O578.5 (3)C14—C13—O7—C11−176.33 (19)
O8—C13—C14—C15173.4 (3)C9—C11—O7—C13−164.90 (19)
O7—C13—C14—C15−6.2 (4)C12—C11—O7—C1373.3 (3)

2-Methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate (I)   Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C2–C7 ring.

D—H···AD—HH···AD···AD—H···A
N1—H1···O50.87 (1)1.74 (2)2.593 (3)166 (3)
O4—H4A···O6i0.84 (1)1.67 (1)2.509 (2)175 (5)
C1—H1A···O8ii0.962.583.522 (4)168
C16—H16···O1ii0.932.513.362 (4)153
C21—H21A···O3iii0.962.383.238 (4)148
C7—H7···Cg1iv0.932.893.5882 (1)133
C21—H21B···Cg10.962.913.7651 (1)148

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

Bis-[4-methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate] pentahydrate (II)   Crystal data

2C20H17O8+·2C6H8N·5H2OZ = 1
Mr = 1049.02F(000) = 554
Triclinic, P1Dx = 1.293 Mg m3
a = 7.5106 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.0155 (3) ÅCell parameters from 9138 reflections
c = 18.5203 (5) Åθ = 2.3–23.5°
α = 75.646 (2)°µ = 0.10 mm1
β = 88.438 (2)°T = 296 K
γ = 86.344 (2)°Block, colourless
V = 1346.81 (7) Å30.40 × 0.30 × 0.30 mm

Bis-[4-methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate] pentahydrate (II)   Data collection

Bruker APEXII CCD Diffractometer6749 reflections with I > 2σ(I)
ω and [var phi] scanRint = 0.031
Absorption correction: multi-scan (SADABS; Bruker, 2004)θmax = 25.0°, θmin = 2.1°
Tmin = 0.683, Tmax = 0.746h = −8→8
26169 measured reflectionsk = −11→11
9433 independent reflectionsl = −22→22

Bis-[4-methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate] pentahydrate (II)   Refinement

Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: fullw = 1/[σ2(Fo2) + (0.0673P)2] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.044(Δ/σ)max < 0.001
wR(F2) = 0.121Δρmax = 0.37 e Å3
S = 1.02Δρmin = −0.23 e Å3
9433 reflectionsExtinction correction: SHELXL-2016 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
715 parametersExtinction coefficient: 0.032 (3)
21 restraintsAbsolute structure: Flack x determined using 2690 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: mixedAbsolute structure parameter: 0.6 (3)

Bis-[4-methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate] pentahydrate (II)   Special details

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.

Bis-[4-methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate] pentahydrate (II)   Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.4416 (8)0.4071 (7)0.1428 (3)0.0793 (17)
H1A0.5151670.3287520.1686130.119*
H1B0.3568320.3776240.1129880.119*
H1C0.5151420.4731330.1112640.119*
C20.3443 (7)0.4722 (5)0.1985 (3)0.0532 (12)
C30.3625 (7)0.4182 (5)0.2745 (3)0.0554 (12)
H30.4401790.3413490.2913860.067*
C40.2694 (6)0.4746 (5)0.3259 (2)0.0480 (11)
H40.2833250.4353860.3766720.058*
C50.1548 (6)0.5900 (5)0.3016 (2)0.0402 (10)
C60.1376 (6)0.6468 (5)0.2255 (2)0.0501 (12)
H60.0634060.7257930.2084450.060*
C70.2297 (7)0.5868 (6)0.1754 (2)0.0565 (13)
H70.2142080.6247030.1246420.068*
C80.0476 (6)0.6537 (5)0.3533 (2)0.0412 (10)
C9−0.0219 (5)0.6496 (4)0.4789 (2)0.0380 (10)
H9−0.0280260.7506880.4629540.046*
C10−0.2101 (6)0.5998 (5)0.4849 (2)0.0429 (10)
C110.0718 (5)0.6040 (4)0.5525 (2)0.0364 (9)
H110.0022500.6407660.5895530.044*
C120.2588 (6)0.6587 (5)0.5467 (2)0.0414 (10)
C130.0855 (6)0.3976 (5)0.6475 (2)0.0468 (11)
C140.0943 (6)0.2458 (5)0.6654 (2)0.0475 (11)
C150.0686 (7)0.1740 (5)0.6117 (3)0.0595 (13)
H150.0451140.2222150.5627920.071*
C160.0777 (8)0.0317 (6)0.6302 (3)0.0692 (15)
H160.059400−0.0143550.5934580.083*
C170.1130 (8)−0.0438 (5)0.7013 (3)0.0620 (13)
C180.1433 (8)0.0282 (6)0.7543 (3)0.0716 (16)
H180.170779−0.0206320.8026890.086*
C190.1337 (8)0.1714 (5)0.7370 (3)0.0645 (14)
H190.1538430.2173040.7737000.077*
C200.1240 (10)−0.1987 (6)0.7208 (4)0.0864 (19)
H20A0.149643−0.2331110.7728220.130*
H20B0.012272−0.2308950.7102460.130*
H20C0.217198−0.2310550.6917350.130*
C210.6306 (11)−0.3317 (6)0.7232 (4)0.098 (2)
H21A0.668596−0.3725040.7733010.147*
H21B0.516077−0.3634510.7158580.147*
H21C0.715704−0.3579570.6888240.147*
C220.6171 (8)−0.1767 (5)0.7099 (3)0.0630 (14)
C230.5652 (8)−0.0962 (6)0.6422 (3)0.0689 (15)
H230.537456−0.1361440.6040000.083*
C240.5544 (8)0.0457 (7)0.6313 (3)0.0759 (16)
H240.5200430.1013610.5851430.091*
C250.6426 (9)0.0252 (7)0.7530 (4)0.0848 (18)
H250.6689380.0669640.7907240.102*
C260.6538 (8)−0.1122 (6)0.7648 (3)0.0705 (15)
H260.687538−0.1657710.8114870.085*
C270.6262 (8)−0.4418 (6)0.9500 (3)0.0718 (15)
H27A0.725863−0.3997200.9647700.108*
H27B0.613947−0.5311170.9832460.108*
H27C0.645700−0.4517450.9000930.108*
C280.4590 (7)−0.3526 (5)0.9529 (3)0.0509 (11)
C290.2947 (7)−0.3880 (5)0.9345 (3)0.0604 (13)
H290.286017−0.4701710.9203700.072*
C300.1436 (7)−0.3039 (5)0.9365 (3)0.0556 (12)
H300.034756−0.3280880.9223530.067*
C310.1530 (6)−0.1832 (4)0.9597 (2)0.0405 (10)
C320.3143 (6)−0.1487 (5)0.9793 (3)0.0485 (11)
H320.321834−0.0687760.9956970.058*
C330.4662 (6)−0.2312 (5)0.9749 (3)0.0537 (12)
H330.575636−0.2045050.9869970.064*
C34−0.0084 (6)−0.0889 (4)0.9560 (2)0.0412 (10)
C35−0.1137 (5)0.1186 (4)0.9861 (2)0.0373 (9)
H35−0.1257250.1531990.9319760.045*
C36−0.2969 (6)0.0908 (5)1.0201 (2)0.0422 (10)
C37−0.0266 (5)0.2267 (4)1.0163 (2)0.0375 (9)
H37−0.0860940.3175710.9955420.045*
C380.1718 (6)0.2300 (4)0.9941 (3)0.0408 (10)
C39−0.0725 (6)0.2939 (5)1.1298 (2)0.0449 (11)
C40−0.1118 (5)0.2436 (4)1.2100 (2)0.0406 (10)
C41−0.1176 (7)0.3368 (5)1.2554 (3)0.0563 (13)
H41−0.0944980.4287111.2347990.068*
C42−0.1569 (7)0.2937 (6)1.3295 (3)0.0594 (13)
H42−0.1597160.3571091.3587240.071*
C43−0.1928 (7)0.1577 (6)1.3625 (3)0.0580 (13)
C44−0.1860 (7)0.0669 (5)1.3175 (3)0.0578 (13)
H44−0.208865−0.0249481.3383710.069*
C45−0.1464 (6)0.1078 (5)1.2426 (3)0.0496 (11)
H45−0.1428270.0437801.2137060.059*
C46−0.2300 (10)0.1089 (7)1.4447 (3)0.0859 (19)
H46A−0.2298660.1855431.4672320.129*
H46B−0.3445440.0697991.4524750.129*
H46C−0.1394800.0401541.4670380.129*
C47−0.7287 (12)0.0319 (10)1.3715 (6)0.136 (3)
H47A−0.7901370.1142471.3429280.204*
H47B−0.812131−0.0238491.4038180.204*
H47C−0.6385760.0564791.4008920.204*
C48−0.6451 (8)−0.0458 (8)1.3212 (4)0.0847 (19)
C49−0.5482 (9)−0.1688 (8)1.3487 (4)0.087 (2)
H49−0.540336−0.2035471.4000630.104*
C50−0.4674 (10)−0.2378 (9)1.3051 (5)0.095 (2)
H50−0.403703−0.3209751.3250290.114*
C51−0.5745 (12)−0.0702 (12)1.1991 (5)0.115 (3)
H51−0.581512−0.0389411.1475390.139*
C52−0.6604 (9)−0.0004 (9)1.2439 (5)0.105 (3)
H52−0.7308840.0789551.2232870.126*
N10.5918 (7)0.1026 (5)0.6848 (3)0.0730 (13)
N2−0.4772 (8)−0.1875 (8)1.2309 (4)0.1036 (19)
O1−0.0614 (5)0.7494 (4)0.33454 (18)0.0651 (10)
O20.0829 (4)0.5948 (3)0.42562 (14)0.0419 (7)
O3−0.2586 (4)0.5169 (4)0.45325 (19)0.0651 (10)
O4−0.3076 (4)0.6597 (4)0.52791 (19)0.0626 (9)
H4A−0.4020280.6217470.5373930.094*
O50.2675 (4)0.7843 (4)0.5287 (2)0.0632 (9)
O60.3893 (4)0.5698 (4)0.55959 (18)0.0569 (8)
O70.0901 (6)0.4658 (4)0.69297 (17)0.0749 (11)
O80.0755 (4)0.4557 (3)0.57457 (14)0.0423 (7)
O9−0.1347 (4)−0.0835 (4)0.91686 (18)0.0609 (9)
O100.0060 (3)−0.0014 (3)1.00073 (15)0.0415 (7)
O11−0.3342 (4)−0.0201 (3)1.05921 (19)0.0578 (8)
O12−0.4032 (4)0.1993 (4)1.0006 (2)0.0639 (9)
H12−0.4788070.1994451.0334170.096*
O130.2042 (4)0.2724 (4)0.92676 (18)0.0569 (8)
O140.2833 (4)0.1877 (3)1.04482 (18)0.0512 (8)
O15−0.0519 (4)0.1899 (3)1.09612 (14)0.0409 (7)
O16−0.0613 (5)0.4136 (4)1.09713 (19)0.0693 (10)
H2−0.402 (7)−0.241 (5)1.204 (3)0.106 (17)*
O17−0.2550 (9)−0.3002 (6)1.1321 (3)0.1186 (17)
H17A−0.199 (12)−0.363 (6)1.112 (4)0.142*
H17B−0.263 (12)−0.225 (5)1.094 (3)0.142*
O18−0.0808 (7)0.4142 (7)0.8384 (2)0.123 (2)
H18B−0.036 (10)0.453 (9)0.796 (2)0.147*
H18A0.000 (8)0.383 (9)0.869 (3)0.147*
O190.5407 (11)0.3153 (8)0.8300 (3)0.145 (2)
H19A0.660 (5)0.323 (12)0.832 (3)0.174*
H19B0.518 (9)0.271 (10)0.876 (3)0.174*
O200.5618 (8)0.3695 (4)0.6789 (3)0.1005 (16)
H20E0.513 (10)0.448 (5)0.648 (3)0.121*
H20D0.545 (10)0.393 (7)0.7215 (19)0.121*
O210.4508 (6)0.3247 (4)0.5022 (2)0.0807 (12)
H21E0.554 (5)0.355 (6)0.492 (4)0.097*
H21D0.383 (6)0.375 (6)0.520 (4)0.097*
H10.572 (7)0.191 (3)0.683 (3)0.070 (17)*

Bis-[4-methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate] pentahydrate (II)   Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.070 (4)0.110 (5)0.068 (3)−0.006 (4)0.014 (3)−0.043 (3)
C20.047 (3)0.067 (3)0.050 (3)−0.010 (3)0.007 (2)−0.022 (2)
C30.053 (3)0.061 (3)0.054 (3)0.004 (3)0.004 (2)−0.019 (2)
C40.050 (3)0.052 (3)0.040 (2)0.005 (2)0.000 (2)−0.009 (2)
C50.035 (2)0.051 (3)0.036 (2)−0.004 (2)−0.0002 (18)−0.0120 (19)
C60.046 (3)0.056 (3)0.042 (3)−0.003 (2)−0.001 (2)0.000 (2)
C70.056 (3)0.079 (4)0.032 (2)−0.013 (3)0.004 (2)−0.009 (2)
C80.035 (2)0.044 (3)0.042 (2)−0.002 (2)−0.003 (2)−0.007 (2)
C90.029 (2)0.043 (2)0.043 (2)0.0018 (19)0.0050 (18)−0.0137 (19)
C100.035 (2)0.052 (3)0.041 (2)−0.001 (2)−0.0019 (19)−0.010 (2)
C110.032 (2)0.039 (2)0.039 (2)−0.0035 (19)0.0043 (17)−0.0111 (18)
C120.031 (2)0.054 (3)0.040 (2)−0.004 (2)−0.0010 (18)−0.013 (2)
C130.049 (3)0.051 (3)0.039 (3)−0.009 (2)0.005 (2)−0.009 (2)
C140.046 (3)0.051 (3)0.043 (2)−0.008 (2)0.006 (2)−0.005 (2)
C150.075 (4)0.048 (3)0.055 (3)−0.011 (3)−0.011 (2)−0.009 (2)
C160.079 (4)0.064 (4)0.069 (4)−0.016 (3)−0.013 (3)−0.021 (3)
C170.065 (3)0.047 (3)0.072 (4)−0.008 (3)0.009 (3)−0.009 (3)
C180.094 (4)0.059 (4)0.051 (3)0.006 (3)0.014 (3)0.002 (3)
C190.085 (4)0.063 (4)0.044 (3)−0.006 (3)0.010 (3)−0.010 (2)
C200.102 (5)0.055 (3)0.097 (5)−0.007 (3)0.011 (4)−0.009 (3)
C210.136 (6)0.052 (4)0.104 (5)−0.003 (4)−0.013 (4)−0.016 (3)
C220.071 (4)0.049 (3)0.067 (3)−0.006 (3)0.001 (3)−0.011 (3)
C230.082 (4)0.064 (4)0.058 (3)−0.006 (3)−0.006 (3)−0.010 (3)
C240.071 (4)0.079 (4)0.068 (4)0.000 (3)0.002 (3)0.000 (3)
C250.096 (5)0.077 (5)0.090 (5)−0.005 (4)−0.016 (4)−0.035 (4)
C260.087 (4)0.065 (4)0.059 (3)0.000 (3)−0.016 (3)−0.015 (3)
C270.068 (4)0.061 (3)0.089 (4)0.016 (3)0.009 (3)−0.027 (3)
C280.050 (3)0.043 (3)0.060 (3)0.005 (2)0.007 (2)−0.015 (2)
C290.065 (3)0.045 (3)0.080 (3)−0.003 (3)0.005 (3)−0.033 (3)
C300.048 (3)0.053 (3)0.073 (3)−0.009 (2)0.000 (2)−0.027 (3)
C310.036 (2)0.045 (2)0.042 (2)−0.005 (2)0.0029 (18)−0.0124 (19)
C320.041 (3)0.042 (3)0.067 (3)0.005 (2)−0.003 (2)−0.024 (2)
C330.038 (3)0.052 (3)0.077 (3)0.000 (2)0.001 (2)−0.030 (2)
C340.033 (2)0.049 (3)0.044 (2)−0.002 (2)0.001 (2)−0.016 (2)
C350.025 (2)0.048 (2)0.038 (2)0.0000 (19)−0.0012 (16)−0.0098 (18)
C360.028 (2)0.050 (3)0.049 (2)−0.001 (2)−0.001 (2)−0.015 (2)
C370.027 (2)0.044 (2)0.038 (2)0.0034 (18)0.0004 (17)−0.0060 (19)
C380.031 (2)0.042 (2)0.051 (3)−0.006 (2)0.008 (2)−0.014 (2)
C390.038 (3)0.049 (3)0.052 (3)−0.007 (2)−0.003 (2)−0.019 (2)
C400.032 (2)0.048 (3)0.044 (2)−0.003 (2)−0.0004 (18)−0.015 (2)
C410.060 (3)0.056 (3)0.060 (3)−0.009 (3)0.001 (2)−0.026 (2)
C420.067 (3)0.064 (3)0.057 (3)−0.004 (3)0.005 (2)−0.034 (3)
C430.053 (3)0.074 (4)0.049 (3)0.002 (3)0.003 (2)−0.021 (3)
C440.061 (3)0.053 (3)0.056 (3)−0.003 (3)0.002 (2)−0.009 (2)
C450.053 (3)0.048 (3)0.052 (3)−0.003 (2)0.001 (2)−0.020 (2)
C460.102 (5)0.100 (5)0.054 (3)−0.005 (4)0.015 (3)−0.019 (3)
C470.092 (6)0.129 (7)0.165 (9)−0.001 (5)0.005 (6)0.002 (7)
C480.047 (3)0.106 (5)0.087 (5)−0.017 (4)0.010 (3)0.003 (4)
C490.055 (4)0.095 (5)0.091 (5)−0.021 (4)−0.016 (4)0.019 (4)
C500.062 (4)0.108 (6)0.104 (6)−0.014 (4)−0.020 (4)0.002 (5)
C510.074 (5)0.156 (8)0.088 (5)−0.022 (6)0.009 (5)0.027 (6)
C520.055 (4)0.122 (6)0.101 (6)−0.008 (4)0.003 (4)0.040 (5)
N10.077 (3)0.047 (3)0.096 (4)−0.008 (3)0.013 (3)−0.018 (3)
N20.060 (4)0.130 (6)0.116 (6)−0.032 (4)0.005 (4)−0.014 (5)
O10.071 (2)0.066 (2)0.0521 (19)0.023 (2)−0.0061 (17)−0.0089 (16)
O20.0363 (16)0.0536 (18)0.0340 (15)0.0039 (14)0.0027 (12)−0.0094 (13)
O30.051 (2)0.081 (2)0.076 (2)−0.0193 (19)0.0088 (17)−0.042 (2)
O40.0320 (17)0.089 (3)0.080 (2)−0.0067 (17)0.0121 (16)−0.045 (2)
O50.048 (2)0.057 (2)0.087 (2)−0.0149 (17)−0.0003 (18)−0.0182 (18)
O60.0296 (17)0.072 (2)0.066 (2)−0.0004 (17)0.0003 (14)−0.0113 (17)
O70.128 (3)0.058 (2)0.0402 (18)−0.007 (2)0.0018 (19)−0.0143 (16)
O80.0449 (17)0.0438 (17)0.0377 (16)−0.0053 (14)0.0003 (13)−0.0089 (13)
O90.045 (2)0.081 (2)0.065 (2)0.0000 (17)−0.0126 (17)−0.0335 (18)
O100.0332 (16)0.0478 (18)0.0450 (16)0.0081 (14)−0.0070 (13)−0.0164 (13)
O110.0451 (19)0.055 (2)0.067 (2)−0.0086 (16)0.0124 (16)−0.0047 (18)
O120.0275 (17)0.062 (2)0.095 (3)0.0001 (16)0.0108 (16)−0.0071 (19)
O130.0412 (19)0.072 (2)0.054 (2)−0.0065 (16)0.0116 (15)−0.0092 (16)
O140.0242 (15)0.072 (2)0.0581 (18)0.0020 (15)−0.0043 (14)−0.0187 (16)
O150.0349 (16)0.0486 (17)0.0404 (15)0.0000 (13)0.0038 (12)−0.0141 (14)
O160.098 (3)0.052 (2)0.060 (2)−0.020 (2)0.008 (2)−0.0156 (18)
O170.119 (5)0.115 (4)0.106 (4)0.004 (4)−0.017 (3)0.002 (3)
O180.122 (4)0.168 (5)0.054 (2)0.073 (4)0.009 (3)−0.006 (3)
O190.223 (8)0.147 (5)0.069 (3)−0.015 (6)−0.010 (4)−0.031 (3)
O200.154 (5)0.066 (3)0.084 (3)0.006 (3)−0.025 (3)−0.026 (2)
O210.089 (3)0.067 (3)0.084 (3)−0.005 (2)0.012 (2)−0.016 (2)

Bis-[4-methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate] pentahydrate (II)   Geometric parameters (Å, º)

C1—C21.502 (7)C29—H290.9300
C1—H1A0.9600C30—C311.385 (6)
C1—H1B0.9600C30—H300.9300
C1—H1C0.9600C31—C321.363 (6)
C2—C71.376 (7)C31—C341.481 (6)
C2—C31.384 (7)C32—C331.378 (6)
C3—C41.377 (6)C32—H320.9300
C3—H30.9300C33—H330.9300
C4—C51.384 (6)C34—O91.201 (5)
C4—H40.9300C34—O101.357 (5)
C5—C61.389 (6)C35—O101.428 (5)
C5—C81.473 (6)C35—C361.511 (6)
C6—C71.375 (7)C35—C371.525 (6)
C6—H60.9300C35—H350.9800
C7—H70.9300C36—O111.211 (5)
C8—O11.208 (5)C36—O121.288 (6)
C8—O21.349 (5)C37—O151.442 (5)
C9—O21.437 (5)C37—C381.536 (6)
C9—C111.505 (6)C37—H370.9800
C9—C101.520 (6)C38—O131.236 (5)
C9—H90.9800C38—O141.250 (5)
C10—O31.207 (5)C39—O161.209 (5)
C10—O41.296 (5)C39—O151.339 (5)
C11—O81.439 (5)C39—C401.474 (6)
C11—C121.531 (6)C40—C451.382 (6)
C11—H110.9800C40—C411.401 (6)
C12—O51.224 (5)C41—C421.363 (7)
C12—O61.267 (5)C41—H410.9300
C13—O71.211 (5)C42—C431.388 (8)
C13—O81.334 (5)C42—H420.9300
C13—C141.471 (6)C43—C441.375 (7)
C14—C191.381 (7)C43—C461.505 (7)
C14—C151.388 (7)C44—C451.376 (7)
C15—C161.378 (7)C44—H440.9300
C15—H150.9300C45—H450.9300
C16—C171.370 (7)C46—H46A0.9600
C16—H160.9300C46—H46B0.9600
C17—C181.385 (8)C46—H46C0.9600
C17—C201.500 (8)C47—C481.461 (12)
C18—C191.387 (7)C47—H47A0.9600
C18—H180.9300C47—H47B0.9600
C19—H190.9300C47—H47C0.9600
C20—H20A0.9600C48—C491.379 (10)
C20—H20B0.9600C48—C521.396 (10)
C20—H20C0.9600C49—C501.303 (11)
C21—C221.508 (8)C49—H490.9300
C21—H21A0.9600C50—N21.344 (10)
C21—H21B0.9600C50—H500.9300
C21—H21C0.9600C51—C521.339 (12)
C22—C231.363 (7)C51—N21.353 (11)
C22—C261.375 (7)C51—H510.9300
C23—C241.382 (8)C52—H520.9300
C23—H230.9300N1—H10.88 (3)
C24—N11.303 (8)N2—H20.97 (3)
C24—H240.9300O4—H4A0.8200
C25—C261.336 (8)O12—H120.8200
C25—N11.359 (8)O17—H17A0.88 (3)
C25—H250.9300O17—H17B0.89 (3)
C26—H260.9300O18—H18B0.85 (3)
C27—C281.502 (7)O18—H18A0.84 (3)
C27—H27A0.9600O19—H19A0.91 (3)
C27—H27B0.9600O19—H19B0.88 (3)
C27—H27C0.9600O20—H20E0.91 (3)
C28—C291.380 (7)O20—H20D0.88 (3)
C28—C331.379 (6)O21—H21E0.85 (3)
C29—C301.375 (7)O21—H21D0.82 (3)
C2—C1—H1A109.5C30—C29—C28121.2 (4)
C2—C1—H1B109.5C30—C29—H29119.4
H1A—C1—H1B109.5C28—C29—H29119.4
C2—C1—H1C109.5C29—C30—C31120.2 (4)
H1A—C1—H1C109.5C29—C30—H30119.9
H1B—C1—H1C109.5C31—C30—H30119.9
C7—C2—C3117.4 (4)C32—C31—C30118.9 (4)
C7—C2—C1120.8 (5)C32—C31—C34121.5 (4)
C3—C2—C1121.8 (5)C30—C31—C34119.3 (4)
C4—C3—C2122.2 (5)C31—C32—C33120.6 (4)
C4—C3—H3118.9C31—C32—H32119.7
C2—C3—H3118.9C33—C32—H32119.7
C3—C4—C5119.5 (4)C32—C33—C28121.2 (4)
C3—C4—H4120.2C32—C33—H33119.4
C5—C4—H4120.2C28—C33—H33119.4
C4—C5—C6119.0 (4)O9—C34—O10122.6 (4)
C4—C5—C8122.5 (4)O9—C34—C31125.9 (4)
C6—C5—C8118.5 (4)O10—C34—C31111.4 (3)
C7—C6—C5120.2 (5)O10—C35—C36113.0 (4)
C7—C6—H6119.9O10—C35—C37106.7 (3)
C5—C6—H6119.9C36—C35—C37111.2 (3)
C6—C7—C2121.6 (4)O10—C35—H35108.6
C6—C7—H7119.2C36—C35—H35108.6
C2—C7—H7119.2C37—C35—H35108.6
O1—C8—O2122.0 (4)O11—C36—O12126.4 (4)
O1—C8—C5124.8 (4)O11—C36—C35123.0 (4)
O2—C8—C5113.2 (4)O12—C36—C35110.5 (4)
O2—C9—C11107.5 (3)O15—C37—C35107.1 (3)
O2—C9—C10110.8 (3)O15—C37—C38111.9 (3)
C11—C9—C10111.2 (3)C35—C37—C38109.8 (3)
O2—C9—H9109.1O15—C37—H37109.3
C11—C9—H9109.1C35—C37—H37109.3
C10—C9—H9109.1C38—C37—H37109.3
O3—C10—O4126.0 (4)O13—C38—O14126.7 (4)
O3—C10—C9123.8 (4)O13—C38—C37115.7 (4)
O4—C10—C9110.2 (4)O14—C38—C37117.5 (4)
O8—C11—C9107.4 (3)O16—C39—O15123.2 (4)
O8—C11—C12112.4 (3)O16—C39—C40125.2 (4)
C9—C11—C12110.9 (3)O15—C39—C40111.6 (4)
O8—C11—H11108.7C45—C40—C41118.2 (4)
C9—C11—H11108.7C45—C40—C39122.7 (4)
C12—C11—H11108.7C41—C40—C39119.1 (4)
O5—C12—O6126.4 (4)C42—C41—C40120.4 (5)
O5—C12—C11116.6 (4)C42—C41—H41119.8
O6—C12—C11117.0 (4)C40—C41—H41119.8
O7—C13—O8121.9 (4)C41—C42—C43121.7 (4)
O7—C13—C14124.8 (4)C41—C42—H42119.1
O8—C13—C14113.2 (4)C43—C42—H42119.1
C19—C14—C15118.4 (4)C44—C43—C42117.4 (4)
C19—C14—C13119.6 (4)C44—C43—C46120.8 (5)
C15—C14—C13121.9 (4)C42—C43—C46121.8 (5)
C16—C15—C14120.5 (5)C45—C44—C43122.0 (5)
C16—C15—H15119.8C45—C44—H44119.0
C14—C15—H15119.8C43—C44—H44119.0
C17—C16—C15121.9 (5)C44—C45—C40120.3 (4)
C17—C16—H16119.1C44—C45—H45119.8
C15—C16—H16119.1C40—C45—H45119.8
C16—C17—C18117.4 (5)C43—C46—H46A109.5
C16—C17—C20121.4 (5)C43—C46—H46B109.5
C18—C17—C20121.1 (5)H46A—C46—H46B109.5
C17—C18—C19121.7 (5)C43—C46—H46C109.5
C17—C18—H18119.1H46A—C46—H46C109.5
C19—C18—H18119.1H46B—C46—H46C109.5
C14—C19—C18120.0 (5)C48—C47—H47A109.5
C14—C19—H19120.0C48—C47—H47B109.5
C18—C19—H19120.0H47A—C47—H47B109.5
C17—C20—H20A109.5C48—C47—H47C109.5
C17—C20—H20B109.5H47A—C47—H47C109.5
H20A—C20—H20B109.5H47B—C47—H47C109.5
C17—C20—H20C109.5C49—C48—C52117.1 (8)
H20A—C20—H20C109.5C49—C48—C47120.8 (7)
H20B—C20—H20C109.5C52—C48—C47122.1 (8)
C22—C21—H21A109.5C50—C49—C48122.0 (7)
C22—C21—H21B109.5C50—C49—H49119.0
H21A—C21—H21B109.5C48—C49—H49119.0
C22—C21—H21C109.5C49—C50—N2119.2 (8)
H21A—C21—H21C109.5C49—C50—H50120.4
H21B—C21—H21C109.5N2—C50—H50120.4
C23—C22—C26118.0 (5)C52—C51—N2118.2 (8)
C23—C22—C21120.1 (5)C52—C51—H51120.9
C26—C22—C21121.9 (5)N2—C51—H51120.9
C22—C23—C24119.1 (5)C51—C52—C48120.6 (8)
C22—C23—H23120.5C51—C52—H52119.7
C24—C23—H23120.5C48—C52—H52119.7
N1—C24—C23120.9 (5)C24—N1—C25121.5 (5)
N1—C24—H24119.6C24—N1—H1124 (4)
C23—C24—H24119.6C25—N1—H1114 (4)
C26—C25—N1118.6 (5)C50—N2—C51122.6 (8)
C26—C25—H25120.7C50—N2—H2112 (3)
N1—C25—H25120.7C51—N2—H2125 (3)
C25—C26—C22122.0 (5)C8—O2—C9115.8 (3)
C25—C26—H26119.0C10—O4—H4A109.5
C22—C26—H26119.0C13—O8—C11116.5 (3)
C28—C27—H27A109.5C34—O10—C35116.2 (3)
C28—C27—H27B109.5C36—O12—H12109.5
H27A—C27—H27B109.5C39—O15—C37116.9 (3)
C28—C27—H27C109.5H17A—O17—H17B104 (4)
H27A—C27—H27C109.5H18B—O18—H18A110 (5)
H27B—C27—H27C109.5H19A—O19—H19B100 (4)
C29—C28—C33117.8 (4)H20E—O20—H20D98 (4)
C29—C28—C27122.1 (4)H21E—O21—H21D114 (5)
C33—C28—C27120.1 (5)
C7—C2—C3—C40.7 (7)C32—C31—C34—O9152.2 (5)
C1—C2—C3—C4−177.8 (5)C30—C31—C34—O9−22.1 (7)
C2—C3—C4—C5−0.8 (8)C32—C31—C34—O10−24.7 (6)
C3—C4—C5—C6−0.4 (7)C30—C31—C34—O10160.9 (4)
C3—C4—C5—C8178.4 (4)O10—C35—C36—O113.9 (5)
C4—C5—C6—C71.7 (7)C37—C35—C36—O11−116.0 (4)
C8—C5—C6—C7−177.3 (4)O10—C35—C36—O12−175.1 (3)
C5—C6—C7—C2−1.7 (7)C37—C35—C36—O1264.9 (4)
C3—C2—C7—C60.6 (7)O10—C35—C37—O15−77.4 (4)
C1—C2—C7—C6179.1 (5)C36—C35—C37—O1546.2 (4)
C4—C5—C8—O1−175.5 (4)O10—C35—C37—C3844.3 (4)
C6—C5—C8—O13.4 (7)C36—C35—C37—C38167.9 (4)
C4—C5—C8—O24.7 (6)O15—C37—C38—O13−173.9 (3)
C6—C5—C8—O2−176.4 (4)C35—C37—C38—O1367.3 (5)
O2—C9—C10—O35.4 (6)O15—C37—C38—O147.4 (5)
C11—C9—C10—O3−114.2 (5)C35—C37—C38—O14−111.4 (4)
O2—C9—C10—O4−174.2 (3)O16—C39—C40—C45171.2 (5)
C11—C9—C10—O466.2 (4)O15—C39—C40—C45−8.2 (6)
O2—C9—C11—O8−62.8 (4)O16—C39—C40—C41−7.7 (7)
C10—C9—C11—O858.7 (4)O15—C39—C40—C41172.9 (4)
O2—C9—C11—C1260.4 (4)C45—C40—C41—C42−0.2 (7)
C10—C9—C11—C12−178.1 (4)C39—C40—C41—C42178.8 (5)
O8—C11—C12—O5−179.4 (3)C40—C41—C42—C43−0.2 (8)
C9—C11—C12—O560.3 (5)C41—C42—C43—C440.5 (8)
O8—C11—C12—O61.7 (5)C41—C42—C43—C46177.9 (5)
C9—C11—C12—O6−118.5 (4)C42—C43—C44—C45−0.4 (8)
O7—C13—C14—C19−9.0 (8)C46—C43—C44—C45−177.8 (5)
O8—C13—C14—C19169.6 (4)C43—C44—C45—C400.0 (8)
O7—C13—C14—C15172.7 (5)C41—C40—C45—C440.3 (7)
O8—C13—C14—C15−8.6 (6)C39—C40—C45—C44−178.6 (4)
C19—C14—C15—C161.7 (8)C52—C48—C49—C502.8 (10)
C13—C14—C15—C16180.0 (5)C47—C48—C49—C50−177.7 (7)
C14—C15—C16—C17−0.4 (9)C48—C49—C50—N20.5 (10)
C15—C16—C17—C18−1.3 (9)N2—C51—C52—C481.9 (12)
C15—C16—C17—C20−179.5 (6)C49—C48—C52—C51−4.1 (10)
C16—C17—C18—C191.7 (9)C47—C48—C52—C51176.5 (8)
C20—C17—C18—C19179.9 (6)C23—C24—N1—C250.0 (9)
C15—C14—C19—C18−1.3 (8)C26—C25—N1—C240.0 (10)
C13—C14—C19—C18−179.6 (5)C49—C50—N2—C51−3.0 (10)
C17—C18—C19—C14−0.4 (9)C52—C51—N2—C501.7 (11)
C26—C22—C23—C241.0 (9)O1—C8—O2—C92.2 (6)
C21—C22—C23—C24−179.8 (6)C5—C8—O2—C9−178.0 (3)
C22—C23—C24—N1−0.5 (9)C11—C9—O2—C8−162.9 (3)
N1—C25—C26—C220.5 (10)C10—C9—O2—C875.3 (4)
C23—C22—C26—C25−1.0 (9)O7—C13—O8—C110.5 (6)
C21—C22—C26—C25179.7 (7)C14—C13—O8—C11−178.2 (3)
C33—C28—C29—C301.2 (8)C9—C11—O8—C13−154.2 (3)
C27—C28—C29—C30−179.1 (5)C12—C11—O8—C1383.6 (4)
C28—C29—C30—C31−2.1 (8)O9—C34—O10—C35−14.8 (6)
C29—C30—C31—C320.9 (7)C31—C34—O10—C35162.2 (3)
C29—C30—C31—C34175.4 (4)C36—C35—O10—C3481.4 (4)
C30—C31—C32—C331.1 (7)C37—C35—O10—C34−156.1 (3)
C34—C31—C32—C33−173.2 (4)O16—C39—O15—C37−4.1 (6)
C31—C32—C33—C28−2.0 (8)C40—C39—O15—C37175.3 (3)
C29—C28—C33—C320.8 (7)C35—C37—O15—C39−146.9 (3)
C27—C28—C33—C32−178.9 (5)C38—C37—O15—C3992.8 (4)

Bis-[4-methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate] pentahydrate (II)   Hydrogen-bond geometry (Å, º)

Cg1 and Cg4 are the centroids of the C2–C7 and C40–C45 rings, respectively.

D—H···AD—HH···AD···AD—H···A
C24—H24···O210.932.413.262 (8)152
C51—H51···O110.932.433.072 (10)127
O4—H4A···O6i0.821.692.503 (4)170
O12—H12···O14i0.821.802.472 (4)138
N2—H2···O170.97 (3)1.89 (3)2.832 (10)164 (5)
O17—H17A···O16ii0.88 (3)2.48 (3)3.330 (7)162 (7)
O17—H17B···O110.89 (3)2.03 (4)2.828 (7)148 (7)
O18—H18B···O70.85 (3)2.09 (5)2.894 (6)157 (9)
O18—H18A···O130.84 (3)2.00 (4)2.815 (6)164 (9)
O19—H19A···O18iii0.91 (3)2.22 (5)3.090 (11)160 (11)
O19—H19B···O12iii0.88 (3)2.32 (5)3.115 (7)151 (7)
O19—H19B···O130.88 (3)2.52 (6)3.048 (8)120 (6)
O20—H20E···O60.91 (3)2.00 (3)2.867 (6)159 (6)
O20—H20D···O190.88 (3)1.97 (4)2.717 (7)142 (6)
O21—H21E···O3iii0.85 (3)2.19 (4)2.976 (5)154 (6)
O21—H21D···O60.82 (3)2.25 (5)2.914 (5)139 (5)
N1—H1···O200.88 (3)1.77 (3)2.644 (6)172 (6)
C41—H41···Cg1iv0.932.903.468 (6)121
C47—H47A···Cg4i0.962.943.707 (10)137

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

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