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Journal logoIUCrDATA
ISSN: 2414-3146

L-Glutaminium 4-methyl­benzene­sulfonate

aDepartment of Physics, Presidency College, Chennai 600 005, Tamil Nadu, India, and bDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203 Tamil Nadu, India
*Correspondence e-mail: ppkpresidency@gmail.com, phdguna@gmail.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 29 December 2016; accepted 31 January 2017; online 14 February 2017)

The asymmetric unit of the title salt, C5H10NO4+·C7H7O3S, contains two glutaminium cations and two 4-methyl­benzene­sulfonate anions. The crystal packing features weak inter­molecular C—H⋯O, O—H⋯O and N—H⋯O hydrogen bonds.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Glutamic acid is a proteinogenic and non-essential amino acid which acts as a neurotransmitter and is essential in the pathology of neurological and psychiatric disorders (Haxhiu et al., 2000[Haxhiu, M., Chavez, J., Pichiule, P., Erokwu, B. & Dreshaj, I. (2000). Brain Res. 883, 77-86.]; Liu et al., 2016[Liu, G., Deng, C., Liao, X., Wang, X., Li, M., Lan, Y., Peng, Y. & Wen, Y. (2016). Int. J. Electrochem. Sci. 11, 650-664.]). Glutamate (L-Glu) is the main excitatory transmitter within the mammalian central nervous system (Tamborini et al., 2016[Tamborini, L., Cullia, G., Nielsen, B., De Micheli, C., Conti, P. & Pinto, A. (2016). Bioorg. Med. Chem. 24, 5741-5747.]). L-Glutamate plays an important role in chronic neurodegenerative and acute diseases such as cerebral ischemia, traumatic brain injury, spinal injury and epilepsy (Hynd et al., 2004[Hynd, M., Scott, H. L. & Dodd, P. R. (2004). Neurochem. Int. 45, 583-595.]).

The asymmetric unit of the title compound comprises two glutaminium cations and two 4-methyl­benzene­sulfonate anions (Fig. 1[link]). The geometric parameters of the title compound agree well with those reported for a similar structure (Thayanithi et al., 2016[Thayanithi, V., Kumar, P. P. & Gunasekaran, B. (2016). IUCrData, 1, x161622-x161622.]). The crystal packing is controlled by weak inter­molecular C—H⋯O, O—H⋯O and N—H⋯O hydrogen bonds (Table 1[link], Fig. 2[link]), forming a three-dimensional structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1C⋯O6 0.86 (1) 2.46 (3) 2.7527 (17) 100 (2)
C2—H2⋯O2 0.93 2.49 2.864 (2) 104
C18—H18⋯O9 0.93 2.53 2.904 (2) 104
N1—H1B⋯O2i 0.87 (2) 2.01 (2) 2.8301 (16) 157 (2)
N2—H2B⋯O8ii 0.86 (1) 2.00 (1) 2.8524 (17) 170 (2)
O7—H7⋯O1iii 0.82 (1) 1.84 (1) 2.6592 (16) 176 (3)
C6—H6⋯O6iv 0.93 2.55 3.316 (2) 140
N2—H2C⋯O14 0.86 (1) 2.50 (2) 2.7803 (18) 100 (2)
N1—H1C⋯O3v 0.86 (1) 2.07 (1) 2.8969 (18) 160 (2)
N2—H2C⋯O9vi 0.86 (1) 2.18 (2) 2.9369 (18) 147 (2)
N1—H1A⋯O1vii 0.88 (2) 2.05 (2) 2.9150 (16) 167 (2)
N2—H2A⋯O10viii 0.87 (1) 2.11 (2) 2.8947 (17) 150 (2)
Symmetry codes: (i) x-1, y, z; (ii) x+1, y+1, z; (iii) x, y-1, z; (iv) x, y+1, z; (v) [-x, y-{\script{1\over 2}}, -z+1]; (vi) [-x+2, y+{\script{1\over 2}}, -z+2]; (vii) [-x+1, y-{\script{1\over 2}}, -z+1]; (viii) [-x+1, y+{\script{1\over 2}}, -z+2].
[Figure 1]
Figure 1
The asymmetric unit of the title compound, showing atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2]
Figure 2
The packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Synthesis and crystallization

The title compound was synthesized by dissolving L-Glutamic acid (0.1 mmol) and p-toluene sulfonic acid monohydrate (0.1 mmol) in 30 ml of deionized water. The solution was stirred for 4 h, filtered into a beaker and kept dust free. Colourless block-shaped crystals were obtained from the mother solution in 93% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C5H10NO4+·C7H7O3S
Mr 319.33
Crystal system, space group Monoclinic, P21
Temperature (K) 295
a, b, c (Å) 5.4540 (3), 8.8013 (5), 30.2297 (18)
β (°) 92.835 (1)
V3) 1449.32 (14)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.26
Crystal size (mm) 0.25 × 0.20 × 0.20
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.])
Tmin, Tmax 0.956, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections 22234, 9991, 8841
Rint 0.019
(sin θ/λ)max−1) 0.769
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.092, 1.03
No. of reflections 9991
No. of parameters 414
No. of restraints 9
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.35, −0.29
Absolute structure Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4563 Friedel pairs
Absolute structure parameter 0.01 (4)
Computer programs: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

L-Glutaminium 4-methylbenzenesulfonate top
Crystal data top
C5H10NO4+·C7H7O3SF(000) = 672
Mr = 319.33Dx = 1.463 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5436 reflections
a = 5.4540 (3) Åθ = 0.7–33.1°
b = 8.8013 (5) ŵ = 0.26 mm1
c = 30.2297 (18) ÅT = 295 K
β = 92.835 (1)°Block, colourless
V = 1449.32 (14) Å30.25 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
9991 independent reflections
Radiation source: fine-focus sealed tube8841 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 0 pixels mm-1θmax = 33.1°, θmin = 0.7°
ω and φ scansh = 88
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1313
Tmin = 0.956, Tmax = 0.975l = 4445
22234 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092 w = 1/[σ2(Fo2) + (0.0469P)2 + 0.186P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.003
9991 reflectionsΔρmax = 0.35 e Å3
414 parametersΔρmin = 0.29 e Å3
9 restraintsAbsolute structure: Flack (1983), 4563 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (4)
Special details top

Refinement. H atoms were positioned geometrically and refined using riding model with C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for C—H, C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H.

One hydroxyl H atom was freely refined with the O—H distance restrained to 0.82 (1) Å, the remaining three using a riding model with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O). The displacement parameter of one riding H atom was refined.

H atoms bonded to N were freely refined with the N—H distances restrained to 0.86 (2) Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.51194 (6)0.76994 (3)0.554874 (11)0.02313 (7)
O10.6281 (2)0.91527 (13)0.54506 (4)0.0359 (3)
O20.6862 (2)0.64604 (13)0.55531 (4)0.0373 (3)
O30.2927 (2)0.74121 (15)0.52729 (4)0.0388 (3)
O60.1221 (2)0.13029 (13)0.54256 (4)0.0357 (3)
O70.4978 (2)0.19277 (13)0.56959 (5)0.0347 (2)
O40.2597 (3)0.3680 (3)0.72528 (4)0.0665 (5)
H40.18580.37890.74800.100*
O50.0963 (3)0.4398 (2)0.69465 (4)0.0541 (4)
N10.0337 (2)0.43370 (15)0.52645 (4)0.0244 (2)
C100.0652 (3)0.40515 (18)0.60781 (5)0.0281 (3)
H10A0.02380.51140.61170.034*
H10B0.08680.34780.60570.034*
C90.1981 (2)0.38670 (14)0.56476 (4)0.0199 (2)
H90.34630.44990.56590.024*
C10.4162 (3)0.78387 (17)0.60965 (5)0.0250 (3)
C80.2681 (3)0.22182 (15)0.55723 (4)0.0217 (2)
C40.2677 (4)0.7993 (2)0.69645 (6)0.0445 (4)
C20.5542 (3)0.7157 (2)0.64356 (6)0.0426 (4)
H20.69750.66400.63760.051*
C120.1120 (3)0.3917 (2)0.69141 (5)0.0369 (4)
C50.1322 (4)0.8685 (2)0.66220 (7)0.0459 (4)
H50.00920.92180.66850.055*
C60.2021 (3)0.8605 (2)0.61848 (6)0.0370 (4)
H60.10700.90560.59570.044*
C110.2190 (3)0.3513 (2)0.64802 (5)0.0370 (4)
H11A0.23680.24180.64640.044*
H11B0.38150.39560.64720.044*
C30.4782 (4)0.7246 (3)0.68669 (6)0.0544 (5)
H30.57260.67880.70940.065*
C70.1889 (6)0.8037 (4)0.74348 (7)0.0708 (7)
H7A0.30140.74530.76200.106*
H7B0.02700.76160.74470.106*
H7C0.18790.90700.75370.106*
H70.532 (5)0.1074 (16)0.5614 (9)0.069 (9)*
H1C0.074 (4)0.368 (2)0.5168 (8)0.056 (7)*
H1B0.048 (4)0.516 (2)0.5314 (7)0.040 (6)*
H1A0.120 (3)0.438 (3)0.5027 (6)0.043 (6)*
S20.47952 (6)0.07804 (4)0.944471 (11)0.02329 (7)
O130.4998 (2)0.34191 (13)0.94161 (4)0.0325 (2)
H130.46300.25480.94830.060 (8)*
O90.7071 (2)0.13081 (14)0.96616 (4)0.0345 (2)
O80.2987 (2)0.19844 (14)0.93747 (5)0.0408 (3)
O140.8813 (2)0.26035 (14)0.95742 (5)0.0424 (3)
O100.3770 (2)0.05506 (13)0.96595 (4)0.0355 (3)
N21.0071 (2)0.56332 (15)0.97136 (4)0.0251 (2)
O111.0828 (3)0.4383 (3)0.80447 (4)0.0597 (4)
O120.7164 (3)0.4973 (2)0.77510 (5)0.0599 (5)
H120.78790.48690.75210.115 (14)*
C210.8273 (3)0.51769 (15)0.93531 (4)0.0205 (2)
H210.68840.58850.93400.025*
C130.5501 (3)0.01743 (16)0.89089 (5)0.0256 (3)
C200.7386 (3)0.35883 (16)0.94638 (5)0.0241 (3)
C220.9485 (3)0.51528 (17)0.89077 (5)0.0269 (3)
H22A1.03580.61000.88690.032*
H22B1.06700.43310.89060.032*
C230.7601 (3)0.4941 (2)0.85277 (5)0.0395 (4)
H23A0.66080.40580.85880.047*
H23B0.65230.58180.85140.047*
C240.8682 (3)0.4742 (2)0.80852 (5)0.0370 (4)
C140.3910 (3)0.0751 (2)0.86642 (6)0.0368 (3)
H140.24940.11120.87880.044*
C180.7653 (3)0.0665 (2)0.87305 (6)0.0380 (3)
H180.87750.12480.88990.046*
C160.6499 (4)0.0616 (2)0.80408 (6)0.0404 (4)
C150.4420 (4)0.1144 (2)0.82343 (6)0.0438 (4)
H150.33410.17760.80730.053*
C170.8114 (4)0.0275 (3)0.82973 (6)0.0470 (5)
H170.95450.06210.81760.056*
C190.6998 (5)0.1001 (3)0.75667 (7)0.0622 (6)
H19A0.66480.01330.73820.093*
H19B0.86910.12810.75480.093*
H19C0.59720.18350.74690.093*
H2C1.114 (3)0.496 (2)0.9792 (8)0.051 (7)*
H2B1.101 (4)0.637 (2)0.9645 (8)0.058 (7)*
H2A0.937 (4)0.576 (3)0.9961 (5)0.054 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02595 (16)0.01870 (14)0.02521 (16)0.00330 (12)0.00599 (12)0.00040 (12)
O10.0419 (6)0.0222 (5)0.0456 (7)0.0002 (5)0.0214 (5)0.0001 (5)
O20.0428 (6)0.0295 (6)0.0406 (6)0.0157 (5)0.0118 (5)0.0005 (5)
O30.0410 (6)0.0429 (7)0.0316 (6)0.0009 (5)0.0061 (5)0.0024 (5)
O60.0406 (6)0.0229 (5)0.0423 (6)0.0007 (5)0.0114 (5)0.0041 (5)
O70.0291 (5)0.0253 (5)0.0493 (7)0.0082 (4)0.0030 (5)0.0074 (5)
O40.0642 (10)0.1150 (15)0.0196 (6)0.0341 (10)0.0059 (6)0.0049 (7)
O50.0538 (8)0.0846 (11)0.0241 (6)0.0257 (8)0.0052 (5)0.0033 (7)
N10.0299 (6)0.0234 (5)0.0197 (5)0.0069 (5)0.0005 (4)0.0019 (5)
C100.0332 (7)0.0324 (7)0.0186 (6)0.0081 (6)0.0019 (5)0.0023 (5)
C90.0228 (6)0.0180 (5)0.0189 (5)0.0016 (4)0.0000 (5)0.0013 (4)
C10.0276 (6)0.0226 (6)0.0254 (6)0.0007 (5)0.0066 (5)0.0004 (5)
C80.0293 (6)0.0183 (5)0.0175 (5)0.0026 (5)0.0011 (5)0.0003 (4)
C40.0560 (11)0.0462 (10)0.0325 (8)0.0029 (8)0.0146 (8)0.0039 (7)
C20.0388 (9)0.0578 (11)0.0312 (8)0.0176 (8)0.0029 (7)0.0016 (8)
C120.0464 (9)0.0440 (9)0.0199 (6)0.0086 (7)0.0010 (6)0.0000 (6)
C50.0456 (10)0.0503 (10)0.0438 (10)0.0121 (8)0.0215 (8)0.0010 (8)
C60.0329 (8)0.0409 (9)0.0379 (9)0.0101 (6)0.0096 (7)0.0044 (7)
C110.0439 (9)0.0463 (9)0.0205 (7)0.0143 (7)0.0005 (6)0.0018 (6)
C30.0629 (13)0.0717 (14)0.0284 (8)0.0182 (11)0.0001 (8)0.0041 (9)
C70.0957 (19)0.0847 (19)0.0346 (10)0.0002 (16)0.0273 (12)0.0037 (12)
S20.02485 (15)0.01980 (15)0.02554 (16)0.00294 (12)0.00467 (12)0.00029 (12)
O130.0313 (5)0.0265 (5)0.0398 (6)0.0075 (4)0.0030 (5)0.0005 (5)
O90.0326 (6)0.0406 (6)0.0301 (6)0.0033 (5)0.0009 (5)0.0021 (5)
O80.0439 (7)0.0346 (6)0.0439 (7)0.0192 (5)0.0029 (6)0.0038 (5)
O140.0424 (7)0.0277 (5)0.0557 (8)0.0020 (5)0.0122 (6)0.0121 (6)
O100.0439 (6)0.0264 (5)0.0379 (6)0.0024 (5)0.0199 (5)0.0007 (5)
N20.0313 (6)0.0243 (5)0.0194 (5)0.0073 (5)0.0003 (5)0.0022 (4)
O110.0579 (9)0.0969 (13)0.0246 (6)0.0214 (9)0.0033 (6)0.0027 (8)
O120.0609 (9)0.0978 (13)0.0202 (6)0.0163 (9)0.0061 (6)0.0025 (7)
C210.0261 (6)0.0183 (5)0.0167 (5)0.0018 (4)0.0015 (5)0.0003 (4)
C130.0288 (7)0.0227 (6)0.0256 (7)0.0025 (5)0.0039 (5)0.0006 (5)
C200.0326 (7)0.0217 (6)0.0178 (6)0.0042 (5)0.0008 (5)0.0002 (5)
C220.0328 (7)0.0296 (7)0.0183 (6)0.0035 (5)0.0022 (5)0.0009 (5)
C230.0399 (9)0.0594 (11)0.0190 (7)0.0061 (8)0.0003 (6)0.0016 (7)
C240.0485 (10)0.0425 (9)0.0195 (6)0.0005 (7)0.0018 (7)0.0011 (6)
C140.0343 (8)0.0421 (9)0.0342 (8)0.0102 (7)0.0023 (6)0.0011 (7)
C180.0365 (8)0.0452 (9)0.0329 (8)0.0109 (7)0.0082 (6)0.0064 (7)
C160.0540 (10)0.0374 (8)0.0302 (8)0.0039 (8)0.0057 (7)0.0024 (7)
C150.0520 (10)0.0450 (10)0.0337 (8)0.0105 (8)0.0030 (8)0.0086 (8)
C170.0456 (10)0.0625 (12)0.0339 (9)0.0077 (9)0.0132 (8)0.0030 (9)
C190.0857 (17)0.0677 (15)0.0342 (10)0.0071 (13)0.0117 (10)0.0102 (10)
Geometric parameters (Å, º) top
S1—O31.4460 (12)S2—O81.4558 (12)
S1—O21.4461 (11)S2—O101.4637 (12)
S1—O11.4642 (12)S2—C131.7657 (15)
S1—C11.7650 (14)O13—C201.3115 (18)
O6—C81.2021 (18)O13—H130.8200
O7—C81.3144 (18)O14—O140.000 (4)
O7—H70.816 (10)O14—C201.2012 (19)
O4—C121.288 (2)N2—C211.4849 (18)
O4—H40.8200N2—H2C0.855 (9)
O5—C121.221 (2)N2—H2B0.858 (7)
N1—C91.4877 (17)N2—H2A0.866 (10)
N1—H1C0.863 (10)O11—C241.224 (2)
N1—H1B0.867 (15)O12—C241.290 (2)
N1—H1A0.878 (15)O12—H120.8200
C10—C111.518 (2)C21—C201.5221 (19)
C10—C91.5295 (19)C21—C221.5293 (19)
C10—H10A0.9700C21—H210.9800
C10—H10B0.9700C13—C141.378 (2)
C9—C81.5205 (18)C13—C181.385 (2)
C9—H90.9800C20—O141.2012 (19)
C1—C21.379 (2)C22—C231.514 (2)
C1—C61.385 (2)C22—H22A0.9700
C4—C31.368 (3)C22—H22B0.9700
C4—C51.383 (3)C23—C241.499 (2)
C4—C71.506 (3)C23—H23A0.9700
C2—C31.390 (3)C23—H23B0.9700
C2—H20.9300C14—C151.386 (2)
C12—C111.504 (2)C14—H140.9300
C5—C61.395 (3)C18—C171.389 (2)
C5—H50.9300C18—H180.9300
C6—H60.9300C16—C151.382 (3)
C11—H11A0.9700C16—C171.387 (3)
C11—H11B0.9700C16—C191.510 (3)
C3—H30.9300C15—H150.9300
C7—H7A0.9600C17—H170.9300
C7—H7B0.9600C19—H19A0.9600
C7—H7C0.9600C19—H19B0.9600
S2—O91.4511 (12)C19—H19C0.9600
O3—S1—O2113.44 (8)O8—S2—O10112.10 (7)
O3—S1—O1112.93 (8)O9—S2—C13106.90 (7)
O2—S1—O1111.71 (7)O8—S2—C13105.28 (7)
O3—S1—C1106.17 (7)O10—S2—C13105.70 (7)
O2—S1—C1105.59 (7)C20—O13—H13109.5
O1—S1—C1106.28 (7)O14—O14—C200 (10)
C8—O7—H7108.7 (19)C21—N2—H2C115.5 (17)
C12—O4—H4109.5C21—N2—H2B114.2 (16)
C9—N1—H1C117.0 (18)H2C—N2—H2B100 (2)
C9—N1—H1B113.1 (15)C21—N2—H2A111.4 (16)
H1C—N1—H1B106 (2)H2C—N2—H2A100 (2)
C9—N1—H1A108.7 (14)H2B—N2—H2A114 (2)
H1C—N1—H1A98 (2)C24—O12—H12109.5
H1B—N1—H1A114 (2)N2—C21—C20107.03 (11)
C11—C10—C9112.44 (12)N2—C21—C22110.56 (11)
C11—C10—H10A109.1C20—C21—C22109.67 (11)
C9—C10—H10A109.1N2—C21—H21109.8
C11—C10—H10B109.1C20—C21—H21109.8
C9—C10—H10B109.1C22—C21—H21109.8
H10A—C10—H10B107.8C14—C13—C18119.89 (15)
N1—C9—C8107.16 (11)C14—C13—S2120.71 (12)
N1—C9—C10109.87 (11)C18—C13—S2119.38 (12)
C8—C9—C10111.21 (11)O14—C20—O140.00 (15)
N1—C9—H9109.5O14—C20—O13125.09 (14)
C8—C9—H9109.5O14—C20—O13125.09 (14)
C10—C9—H9109.5O14—C20—C21121.01 (14)
C2—C1—C6120.18 (15)O14—C20—C21121.01 (14)
C2—C1—S1119.42 (12)O13—C20—C21113.88 (12)
C6—C1—S1120.39 (12)C23—C22—C21111.28 (13)
O6—C8—O7125.40 (13)C23—C22—H22A109.4
O6—C8—C9121.88 (13)C21—C22—H22A109.4
O7—C8—C9112.70 (12)C23—C22—H22B109.4
C3—C4—C5118.25 (17)C21—C22—H22B109.4
C3—C4—C7119.8 (2)H22A—C22—H22B108.0
C5—C4—C7121.9 (2)C24—C23—C22114.17 (15)
C1—C2—C3119.73 (16)C24—C23—H23A108.7
C1—C2—H2120.1C22—C23—H23A108.7
C3—C2—H2120.1C24—C23—H23B108.7
O5—C12—O4122.72 (16)C22—C23—H23B108.7
O5—C12—C11123.67 (15)H23A—C23—H23B107.6
O4—C12—C11113.60 (15)O11—C24—O12122.82 (17)
C4—C5—C6121.72 (17)O11—C24—C23122.67 (15)
C4—C5—H5119.1O12—C24—C23114.51 (16)
C6—C5—H5119.1C13—C14—C15120.04 (16)
C1—C6—C5118.65 (17)C13—C14—H14120.0
C1—C6—H6120.7C15—C14—H14120.0
C5—C6—H6120.7C13—C18—C17119.12 (16)
C12—C11—C10113.67 (13)C13—C18—H18120.4
C12—C11—H11A108.8C17—C18—H18120.4
C10—C11—H11A108.8C15—C16—C17117.71 (17)
C12—C11—H11B108.8C15—C16—C19121.06 (19)
C10—C11—H11B108.8C17—C16—C19121.23 (19)
H11A—C11—H11B107.7C16—C15—C14121.30 (17)
C4—C3—C2121.45 (18)C16—C15—H15119.4
C4—C3—H3119.3C14—C15—H15119.4
C2—C3—H3119.3C16—C17—C18121.84 (18)
C4—C7—H7A109.5C16—C17—H17119.1
C4—C7—H7B109.5C18—C17—H17119.1
H7A—C7—H7B109.5C16—C19—H19A109.5
C4—C7—H7C109.5C16—C19—H19B109.5
H7A—C7—H7C109.5H19A—C19—H19B109.5
H7B—C7—H7C109.5C16—C19—H19C109.5
O9—S2—O8113.01 (8)H19A—C19—H19C109.5
O9—S2—O10113.11 (8)H19B—C19—H19C109.5
C11—C10—C9—N1177.06 (13)O10—S2—C13—C1441.80 (16)
C11—C10—C9—C858.59 (17)O9—S2—C13—C1818.89 (16)
O3—S1—C1—C2137.98 (15)O8—S2—C13—C18101.54 (15)
O2—S1—C1—C217.26 (16)O10—S2—C13—C18139.65 (14)
O1—S1—C1—C2101.53 (15)O14—O14—C20—O130.0 (6)
O3—S1—C1—C640.99 (15)O14—O14—C20—C210.0 (6)
O2—S1—C1—C6161.71 (14)N2—C21—C20—O1447.36 (18)
O1—S1—C1—C679.50 (15)C22—C21—C20—O1472.62 (18)
N1—C9—C8—O640.23 (18)N2—C21—C20—O1447.36 (18)
C10—C9—C8—O679.86 (17)C22—C21—C20—O1472.62 (18)
N1—C9—C8—O7141.59 (12)N2—C21—C20—O13134.14 (13)
C10—C9—C8—O798.32 (14)C22—C21—C20—O13105.88 (14)
C6—C1—C2—C30.2 (3)N2—C21—C22—C23170.78 (13)
S1—C1—C2—C3179.20 (17)C20—C21—C22—C2371.43 (16)
C3—C4—C5—C61.6 (3)C21—C22—C23—C24173.86 (14)
C7—C4—C5—C6178.1 (2)C22—C23—C24—O1118.2 (3)
C2—C1—C6—C50.8 (3)C22—C23—C24—O12162.05 (18)
S1—C1—C6—C5179.78 (15)C18—C13—C14—C152.4 (3)
C4—C5—C6—C11.5 (3)S2—C13—C14—C15176.17 (15)
O5—C12—C11—C1011.8 (3)C14—C13—C18—C173.2 (3)
O4—C12—C11—C10169.55 (18)S2—C13—C18—C17175.38 (16)
C9—C10—C11—C12170.29 (14)C17—C16—C15—C142.5 (3)
C5—C4—C3—C20.9 (4)C19—C16—C15—C14177.8 (2)
C7—C4—C3—C2178.8 (2)C13—C14—C15—C160.5 (3)
C1—C2—C3—C40.3 (4)C15—C16—C17—C181.6 (3)
O9—S2—C13—C14162.57 (14)C19—C16—C17—C18178.6 (2)
O8—S2—C13—C1477.01 (15)C13—C18—C17—C161.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O60.86 (1)2.46 (3)2.7527 (17)100 (2)
C2—H2···O20.932.492.864 (2)104
C18—H18···O90.932.532.904 (2)104
N1—H1B···O2i0.87 (2)2.01 (2)2.8301 (16)157 (2)
N2—H2B···O8ii0.86 (1)2.00 (1)2.8524 (17)170 (2)
O7—H7···O1iii0.82 (1)1.84 (1)2.6592 (16)176 (3)
C6—H6···O6iv0.932.553.316 (2)140
N2—H2C···O140.86 (1)2.50 (2)2.7803 (18)100 (2)
N1—H1C···O3v0.86 (1)2.07 (1)2.8969 (18)160 (2)
N2—H2C···O9vi0.86 (1)2.18 (2)2.9369 (18)147 (2)
N1—H1A···O1vii0.88 (2)2.05 (2)2.9150 (16)167 (2)
N2—H2A···O10viii0.87 (1)2.11 (2)2.8947 (17)150 (2)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z; (iii) x, y1, z; (iv) x, y+1, z; (v) x, y1/2, z+1; (vi) x+2, y+1/2, z+2; (vii) x+1, y1/2, z+1; (viii) x+1, y+1/2, z+2.
 

Acknowledgements

The authors acknowledge the SAIF, IIT Madras, Chennai.

References

First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHaxhiu, M., Chavez, J., Pichiule, P., Erokwu, B. & Dreshaj, I. (2000). Brain Res. 883, 77–86.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHynd, M., Scott, H. L. & Dodd, P. R. (2004). Neurochem. Int. 45, 583–595.  Web of Science CrossRef PubMed CAS Google Scholar
First citationLiu, G., Deng, C., Liao, X., Wang, X., Li, M., Lan, Y., Peng, Y. & Wen, Y. (2016). Int. J. Electrochem. Sci. 11, 650–664.  CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTamborini, L., Cullia, G., Nielsen, B., De Micheli, C., Conti, P. & Pinto, A. (2016). Bioorg. Med. Chem. 24, 5741–5747.  Web of Science CrossRef CAS PubMed Google Scholar
First citationThayanithi, V., Kumar, P. P. & Gunasekaran, B. (2016). IUCrData, 1, x161622–x161622.  Google Scholar

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