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ISSN: 2414-3146

Sulfamerazine tetra­hydro­furan monosolvate

aDepartment of Chemistry, University of Dhaka, Dhaka-1000, Bangladesh
*Correspondence e-mail: acsbd@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 3 April 2016; accepted 10 April 2016; online 15 April 2016)

The title solvate, C11H12N4O2S·C4H8O, crystallizes with three mol­ecules of sulfamerazine [4-amino-N-(4-methyl­pyrimidin-2-yl)benzene­sulfonamide] and three mol­ecules of tetra­hydro­furan solvent in the asymmetric unit. The dihedral angles between the aromatic rings in the sulfamerazine mol­ecules are 83.40 (12), 87.40 (12) and 89.54 (12)°. In the crystal, mol­ecules are linked by N—H⋯O and N—H⋯N hydrogen bonds, generating (10-6) sheets.

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

Structure description

This is the first crystal structure of solvated sulfamerazine. The structure of three polymorphs of sulfamerazine have been published in space groups Pbca (Acharya et al., 1982[Acharya, K. R., Kuchela, K. N. & Kartha, G. (1982). J. Crystallogr. Spectrosc. Res. 12, 369-376.]), Pna21 (Caria & Mohamed, 1992[Caria, M. R. & Mohamed, R. (1992). Acta Cryst. B48, 492-498.]) and P21/c (Hossain, 2006[Hossain, G. M. G. (2006). Acta Cryst. E62, o2166-o2167.]).

The endocyclic N—C—N angles (pyrimidine ring) of 127.0 (2)–127.5 (2)° in the title compound (Fig. 1[link]) are comparable with the corresponding values in the polymorphs of sulfamerazine; these angles are considerably larger than the value usually observed for a pyrimidine ring.

[Figure 1]
Figure 1
The mol­ecular structure with 30% probability displacement ellipsoids for non-H atoms.

The planes of the benzene and pyrimidine rings are inclined to each other by 83.40 (12)–89.54 (12)°; these dihedral angles are larger than the corresponding values of 71 (1)° (Acharya et al., 1982[Acharya, K. R., Kuchela, K. N. & Kartha, G. (1982). J. Crystallogr. Spectrosc. Res. 12, 369-376.]), 61.5 (5) and 58.5 (5)° (Caria & Mohamed, 1992[Caria, M. R. & Mohamed, R. (1992). Acta Cryst. B48, 492-498.]) and 64.39 (2)° (Hossain, 2006[Hossain, G. M. G. (2006). Acta Cryst. E62, o2166-o2167.]) in the polymorphs of sulfamerazine. This may be due to the solvation of the tetra­hydro­furan mol­ecules hydrogen bonded to the sulfamerazine mol­ecules. The torsion angles of the sulfamerazine mol­ecule in this solvate indicate that the sulfamerazine mol­ecules adopt a gauche conformation when viewed along the S—N vector.

In the crystal, mol­ecules are linked by N—H⋯O and N—H⋯N hydrogen bonds (Table 1[link]), generating (10[\overline{6}]) sheets.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N14—H14B⋯O32 0.88 2.11 2.968 (3) 166
N14—H14A⋯O41 0.88 2.40 3.051 (3) 131
N24—H24A⋯O42 0.88 2.29 2.998 (3) 137
N34—H34B⋯O43 0.88 2.30 2.983 (3) 134
N11—H11⋯N23i 0.88 2.04 2.913 (3) 169
N21—H21⋯N13ii 0.88 2.00 2.873 (3) 172
N24—H24B⋯O21iii 0.88 2.17 2.999 (3) 158
N31—H31⋯N33iv 0.88 2.02 2.893 (3) 174
N34—H34A⋯O11v 0.88 2.15 3.009 (3) 167
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) -x+2, -y+2, -z+2; (v) x, y+1, z.

Synthesis and crystallization

Solid sulfamerazine (0.5446 g, 2 mmol) was dissolved in 50 ml of hot methanol and a methano­lic solution of CuCl2·2H2O (0.1705 g, 1 mmol) was added slowly with constant stirring on a hot plate. A red precipitate was formed and stirring was continued six hours. The precipitate was filtered and dried over silica gel. The red precipitate was dissolved in THF solution, filtered and left for crystallization at 273 K. Two weeks later, colorless blocks were filtered and dried over silica gel.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The mosaicity of the diffraction pattern was high and it did not diffract well so the Rint value is high.

Table 2
Experimental details

Crystal data
Chemical formula C11H12N4O2S·C4H8O
Mr 336.41
Crystal system, space group Monoclinic, P21/c
Temperature (K) 150
a, b, c (Å) 10.5765 (2), 11.8088 (2), 39.1512 (7)
β (°) 92.618 (1)
V3) 4884.71 (15)
Z 12
Radiation type Mo Kα
μ (mm−1) 0.22
Crystal size (mm) 0.25 × 0.22 × 0.20
 
Data collection
Diffractometer Nonius KappaCCD
Absorption correction Multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.])
Tmin, Tmax 0.947, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections 26393, 10636, 6070
Rint 0.119
(sin θ/λ)max−1) 0.649
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.169, 1.01
No. of reflections 10636
No. of parameters 625
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.41, −0.58
Computer programs: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]; Nonius, 2004[Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.]), (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Structural data


Synthesis and crystallization top

Solid sulfamerazine (0.5446 g, 2 mmol) was dissolved in 50 ml of hot methanol and a methano­lic solution of CuCl2.2H2O (0.1705 g, 1 mmol) was added slowly with constant stirring on a hot plate. A red precipitate was formed and the mixture was continued to stir for six hours. The precipitate was filtered and dried over silica gel. The red precipitate was dissolved in THF solution, filtered and left for crystallization at 273 K. Two weeks later, colorless blocks of (I) were filtered and dried over silica gel.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The H atoms were geometrically placed (C—H = 0.95–0.99 Å, N—H = 0.88–0.90Å) and refined as riding with Uiso(H) = xUeq(C,N) where x = 1.5 for methyl H and 1.2 for all other H. The mosaicity of the diffraction pattern was high and it did not diffract well so the Rint is high. Crystal data, data collection and structure refinement details are summarized in Table 1.

Experimental top

Solid sulfamerazine (0.5446 g, 2 mmol) was dissolved in 50 ml of hot methanol and a methanolic solution of CuCl2·2H2O (0.1705 g, 1 mmol) was added slowly with constant stirring on a hot plate. A red precipitate was formed and the mixture was continued to stir for six hours. The precipitate was filtered and dried over silica gel. The red precipitate was dissolved in THF solution, filtered and left for crystallization at 273 K. Two weeks later, colorless blocks were filtered and dried over silica gel.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The mosaicity of the diffraction pattern was high and it did not diffract well so the Rint value is high.

Structure description top

This is the first crystal structure of solvated sulfamerazine. The structure of three polymorphs of sulfamerazine have been published in space groups Pbca (Acharya et al., 1982), Pna21 (Caria & Mohamed, 1992) and P21/c (Hossain, 2006).

The endocyclic N—C—N angles (pyrimidine ring) of 127.0 (2)–127.5 (2)° in the title compound are comparable with the corresponding values in the polymorphs of sulfamerazine; these angles are considerably larger than the value usually observed for a pyrimidine ring.

The planes of the benzene and pyrimidine rings are inclined to each other by 83.40 (12)–89.54 (12)°; these dihedral angles are larger than the corresponding values of 71 (1)° (Acharya et al., 1982), 61.5 (5) and 58.5 (5)° (Caria & Mohamed, 1992) and 64.39 (2)° (Hossain, 2006) in the polymorphs of sulfamerazine. This may be due to the solvation of the tetrahydrofuran molecule hydrogen bonded to the sulfamerazine molecules. The torsion angles of the sulfamerazine molecule in this solvate indicate that the sulfamerazine molecules adopt a gauche conformation when viewed along the S—N vector.

In the crystal, molecules are linked by N—H···O and N—H···N hydrogen bonds (Table 1), generating (106) sheets.

Computing details top

Data collection: COLLECT (Hooft, 1998; Nonius, 2004); cell refinement: (Otwinowski & Minor, 1997); data reduction: (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. The molecular structure with 30% probability displacement ellipsoids for non-H atoms.
4-Amino-N-(4-methylpyrimidin-2-yl)benzenesulfonamide tetrahydrofuran monosolvate top
Crystal data top
C11H12N4O2S·C4H8OF(000) = 2136
Mr = 336.41Dx = 1.372 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.5765 (2) ÅCell parameters from 10636 reflections
b = 11.8088 (2) Åθ = 2.9–27.5°
c = 39.1512 (7) ŵ = 0.22 mm1
β = 92.618 (1)°T = 150 K
V = 4884.71 (15) Å3Block, colorless
Z = 120.25 × 0.22 × 0.20 mm
Data collection top
Nonius KappaCCD
diffractometer
10636 independent reflections
Radiation source: fine-focus sealed tube6070 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.119
ω and φ scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
h = 1313
Tmin = 0.947, Tmax = 0.957k = 1512
26393 measured reflectionsl = 5050
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.169 w = 1/[σ2(Fo2) + (0.0684P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
10636 reflectionsΔρmax = 0.41 e Å3
625 parametersΔρmin = 0.58 e Å3
Crystal data top
C11H12N4O2S·C4H8OV = 4884.71 (15) Å3
Mr = 336.41Z = 12
Monoclinic, P21/cMo Kα radiation
a = 10.5765 (2) ŵ = 0.22 mm1
b = 11.8088 (2) ÅT = 150 K
c = 39.1512 (7) Å0.25 × 0.22 × 0.20 mm
β = 92.618 (1)°
Data collection top
Nonius KappaCCD
diffractometer
10636 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
6070 reflections with I > 2σ(I)
Tmin = 0.947, Tmax = 0.957Rint = 0.119
26393 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 1.01Δρmax = 0.41 e Å3
10636 reflectionsΔρmin = 0.58 e Å3
625 parameters
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
S110.25291 (6)0.32196 (6)0.86011 (2)0.02129 (18)
S210.73980 (6)0.65993 (6)0.80975 (2)0.02120 (18)
S310.74417 (6)0.83415 (6)0.97168 (2)0.02228 (18)
O110.22462 (17)0.20954 (15)0.87149 (4)0.0262 (4)
O120.30284 (17)0.33533 (16)0.82686 (4)0.0284 (5)
O210.78019 (16)0.76950 (15)0.79868 (4)0.0268 (5)
O220.69177 (17)0.64950 (16)0.84348 (4)0.0287 (5)
O310.68851 (17)0.85232 (16)1.00396 (4)0.0292 (5)
O320.77429 (16)0.72023 (15)0.96177 (4)0.0267 (5)
N110.12207 (19)0.39811 (19)0.85734 (5)0.0247 (5)
H110.09740.42390.83700.030*
N120.08098 (19)0.37871 (19)0.91486 (5)0.0218 (5)
N130.0476 (2)0.49571 (19)0.87746 (5)0.0241 (5)
N140.5984 (2)0.5253 (2)0.96566 (6)0.0341 (6)
H14A0.60440.49510.98620.041*
H14B0.64320.58560.96100.041*
N210.86047 (19)0.5717 (2)0.81117 (5)0.0257 (6)
H210.88370.54290.83120.031*
N220.89790 (19)0.5881 (2)0.75340 (5)0.0237 (5)
N231.0164 (2)0.46017 (19)0.78991 (5)0.0249 (5)
N240.3689 (2)0.4854 (2)0.70574 (6)0.0393 (7)
H24A0.36190.51750.68550.047*
H24B0.32150.42670.71040.047*
N310.87487 (19)0.90998 (19)0.97536 (5)0.0259 (6)
H310.89240.94260.99520.031*
N320.9370 (2)0.87305 (19)0.92019 (5)0.0245 (5)
N331.0552 (2)0.9978 (2)0.95796 (5)0.0272 (6)
N340.4198 (2)1.0297 (2)0.86005 (6)0.0326 (6)
H34A0.37321.09000.86370.039*
H34B0.41860.99850.83960.039*
C110.0479 (2)0.4246 (2)0.88462 (6)0.0200 (6)
C120.0132 (2)0.4121 (2)0.94139 (7)0.0254 (7)
C130.0859 (3)0.4873 (3)0.93699 (7)0.0330 (8)
H130.13350.51110.95570.040*
C140.1132 (3)0.5264 (3)0.90433 (7)0.0336 (8)
H140.18180.57760.90070.040*
C150.3542 (2)0.3840 (2)0.89128 (6)0.0205 (6)
C160.4259 (2)0.4786 (2)0.88334 (7)0.0240 (6)
H160.41860.51090.86110.029*
C170.5076 (2)0.5252 (2)0.90798 (7)0.0264 (7)
H170.55640.58980.90260.032*
C180.5193 (2)0.4785 (2)0.94098 (7)0.0237 (6)
C190.4475 (2)0.3824 (2)0.94814 (7)0.0230 (6)
H190.45580.34870.97020.028*
C200.3653 (2)0.3361 (2)0.92385 (6)0.0212 (6)
H200.31620.27170.92920.025*
C210.9280 (2)0.5395 (2)0.78351 (6)0.0200 (6)
C220.9583 (2)0.5492 (2)0.72655 (7)0.0258 (7)
C231.0500 (3)0.4662 (3)0.73016 (7)0.0320 (7)
H231.09310.43900.71100.038*
C241.0766 (3)0.4242 (3)0.76258 (7)0.0315 (7)
H241.14000.36770.76560.038*
C250.6292 (2)0.6087 (2)0.77938 (6)0.0203 (6)
C260.6176 (2)0.6598 (2)0.74717 (6)0.0220 (6)
H260.67050.72190.74200.026*
C270.5298 (2)0.6203 (2)0.72295 (7)0.0253 (6)
H270.52090.65670.70130.030*
C280.4536 (2)0.5268 (2)0.73002 (7)0.0249 (6)
C290.4649 (2)0.4768 (2)0.76266 (7)0.0279 (7)
H290.41190.41500.76800.034*
C300.5528 (2)0.5174 (2)0.78696 (7)0.0252 (6)
H300.56080.48270.80880.030*
C310.9596 (2)0.9269 (2)0.94987 (6)0.0223 (6)
C321.0181 (3)0.8950 (2)0.89552 (7)0.0278 (7)
C331.1182 (3)0.9691 (3)0.90116 (7)0.0339 (7)
H331.17490.98520.88370.041*
C341.1330 (3)1.0185 (3)0.93276 (7)0.0349 (8)
H341.20151.06950.93690.042*
C350.6488 (2)0.8931 (2)0.93866 (6)0.0209 (6)
C360.5742 (2)0.9872 (2)0.94514 (7)0.0263 (7)
H360.57591.02000.96730.032*
C370.4979 (2)1.0324 (2)0.91911 (7)0.0271 (7)
H370.44721.09680.92340.032*
C380.4941 (2)0.9845 (2)0.88630 (7)0.0233 (6)
C390.5698 (2)0.8894 (2)0.88041 (7)0.0225 (6)
H390.56790.85580.85830.027*
C400.6465 (2)0.8445 (2)0.90619 (7)0.0223 (6)
H400.69780.78050.90190.027*
C560.0545 (3)0.3624 (3)0.97532 (6)0.0351 (8)
H56A0.13840.39170.98230.053*
H56B0.05830.27970.97340.053*
H56C0.00620.38320.99240.053*
C570.9215 (3)0.6026 (3)0.69277 (7)0.0390 (8)
H57A0.91270.68460.69570.059*
H57B0.84070.57090.68410.059*
H57C0.98700.58720.67650.059*
C580.9911 (3)0.8349 (3)0.86235 (7)0.0419 (9)
H58A0.90730.85710.85290.063*
H58B0.99310.75290.86620.063*
H58C1.05540.85550.84620.063*
O410.75615 (19)0.36623 (19)1.01187 (5)0.0414 (6)
O420.2191 (2)0.6315 (2)0.65606 (6)0.0490 (6)
O430.3115 (2)0.84734 (18)0.81484 (6)0.0484 (6)
C410.7635 (3)0.3445 (3)1.04792 (8)0.0408 (8)
H41A0.74070.41311.06080.049*
H41B0.85010.32091.05550.049*
C420.6696 (3)0.2502 (3)1.05346 (8)0.0472 (9)
H42A0.58700.28111.05980.057*
H42B0.70160.19811.07170.057*
C430.6576 (3)0.1892 (3)1.01893 (8)0.0383 (8)
H43A0.68580.10951.02110.046*
H43B0.56920.19081.00950.046*
C440.7442 (3)0.2564 (3)0.99650 (8)0.0444 (9)
H44A0.82790.21930.99570.053*
H44B0.70690.26230.97290.053*
C450.2034 (3)0.6474 (3)0.61990 (9)0.0538 (10)
H45A0.11320.66090.61330.065*
H45B0.23240.57950.60770.065*
C460.2823 (4)0.7491 (3)0.61114 (9)0.0549 (10)
H46A0.23350.80170.59590.066*
H46B0.35990.72570.59980.066*
C470.3146 (3)0.8040 (3)0.64550 (8)0.0460 (9)
H47A0.40520.79350.65220.055*
H47B0.29520.88600.64490.055*
C480.2318 (3)0.7430 (3)0.66945 (9)0.0500 (9)
H48A0.27150.74150.69280.060*
H48B0.14820.78030.67020.060*
C490.3219 (3)0.7412 (3)0.83223 (9)0.0458 (9)
H49A0.29730.74920.85620.055*
H49B0.40990.71260.83220.055*
C500.2324 (3)0.6605 (3)0.81282 (8)0.0390 (8)
H50A0.15380.64890.82520.047*
H50B0.27320.58620.80930.047*
C510.2048 (3)0.7208 (3)0.77892 (8)0.0482 (9)
H51A0.22040.67000.75940.058*
H51B0.11590.74710.77700.058*
C520.2948 (3)0.8194 (3)0.77967 (8)0.0448 (9)
H52A0.37640.79790.77010.054*
H52B0.25840.88410.76650.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S110.0219 (4)0.0264 (4)0.0156 (3)0.0045 (3)0.0009 (3)0.0011 (3)
S210.0205 (4)0.0252 (4)0.0177 (4)0.0036 (3)0.0004 (3)0.0016 (3)
S310.0202 (4)0.0277 (4)0.0187 (4)0.0072 (3)0.0011 (3)0.0012 (3)
O110.0297 (11)0.0252 (11)0.0233 (10)0.0034 (9)0.0043 (8)0.0012 (8)
O120.0301 (11)0.0396 (13)0.0158 (10)0.0056 (9)0.0058 (8)0.0009 (8)
O210.0274 (10)0.0243 (11)0.0281 (11)0.0002 (9)0.0062 (8)0.0018 (8)
O220.0297 (11)0.0396 (13)0.0170 (10)0.0075 (9)0.0042 (8)0.0020 (8)
O310.0264 (11)0.0451 (13)0.0163 (10)0.0120 (10)0.0027 (8)0.0018 (9)
O320.0277 (10)0.0265 (12)0.0254 (11)0.0049 (9)0.0058 (8)0.0028 (8)
N110.0234 (12)0.0352 (15)0.0153 (12)0.0082 (11)0.0003 (9)0.0033 (10)
N120.0189 (12)0.0307 (14)0.0158 (12)0.0014 (10)0.0008 (9)0.0031 (10)
N130.0239 (12)0.0310 (14)0.0175 (12)0.0067 (11)0.0008 (9)0.0038 (10)
N140.0338 (14)0.0362 (16)0.0319 (14)0.0113 (12)0.0025 (11)0.0015 (11)
N210.0227 (12)0.0367 (15)0.0173 (12)0.0098 (11)0.0023 (9)0.0064 (10)
N220.0211 (12)0.0346 (15)0.0156 (12)0.0039 (11)0.0018 (9)0.0030 (10)
N230.0240 (12)0.0329 (15)0.0179 (12)0.0079 (11)0.0005 (9)0.0002 (10)
N240.0384 (15)0.0485 (18)0.0305 (15)0.0172 (13)0.0051 (12)0.0003 (12)
N310.0220 (12)0.0370 (15)0.0187 (12)0.0103 (11)0.0010 (9)0.0049 (10)
N320.0222 (12)0.0344 (15)0.0168 (12)0.0044 (11)0.0003 (9)0.0016 (10)
N330.0246 (12)0.0380 (15)0.0191 (13)0.0137 (11)0.0013 (10)0.0030 (10)
N340.0346 (14)0.0367 (15)0.0263 (14)0.0110 (12)0.0017 (11)0.0044 (11)
C110.0186 (13)0.0267 (16)0.0146 (14)0.0012 (12)0.0007 (10)0.0015 (11)
C120.0207 (14)0.0381 (18)0.0173 (14)0.0009 (13)0.0012 (11)0.0010 (12)
C130.0306 (16)0.050 (2)0.0184 (15)0.0117 (15)0.0030 (12)0.0041 (13)
C140.0295 (16)0.045 (2)0.0266 (17)0.0152 (15)0.0021 (13)0.0008 (14)
C150.0187 (14)0.0221 (15)0.0209 (14)0.0045 (12)0.0041 (11)0.0029 (11)
C160.0246 (15)0.0255 (16)0.0223 (15)0.0047 (13)0.0048 (12)0.0026 (12)
C170.0264 (15)0.0237 (16)0.0296 (16)0.0037 (13)0.0070 (12)0.0020 (12)
C180.0181 (14)0.0316 (17)0.0215 (15)0.0006 (13)0.0028 (11)0.0045 (12)
C190.0217 (14)0.0275 (16)0.0197 (14)0.0000 (12)0.0003 (11)0.0022 (12)
C200.0197 (14)0.0224 (15)0.0216 (15)0.0020 (12)0.0019 (11)0.0006 (11)
C210.0165 (13)0.0280 (16)0.0155 (14)0.0016 (12)0.0002 (10)0.0011 (11)
C220.0208 (14)0.0369 (18)0.0196 (15)0.0012 (13)0.0003 (11)0.0008 (13)
C230.0311 (16)0.048 (2)0.0168 (15)0.0102 (15)0.0049 (12)0.0028 (13)
C240.0292 (16)0.0389 (19)0.0264 (17)0.0117 (14)0.0009 (13)0.0022 (14)
C250.0193 (14)0.0220 (15)0.0198 (14)0.0029 (12)0.0041 (11)0.0004 (11)
C260.0223 (14)0.0212 (15)0.0226 (15)0.0011 (12)0.0005 (11)0.0000 (11)
C270.0256 (15)0.0283 (17)0.0218 (15)0.0004 (13)0.0004 (12)0.0011 (12)
C280.0210 (14)0.0303 (17)0.0231 (15)0.0015 (13)0.0001 (11)0.0064 (12)
C290.0264 (15)0.0262 (17)0.0317 (17)0.0064 (13)0.0072 (12)0.0009 (13)
C300.0267 (15)0.0279 (17)0.0212 (15)0.0032 (13)0.0040 (12)0.0036 (12)
C310.0211 (14)0.0300 (17)0.0159 (14)0.0023 (12)0.0002 (11)0.0024 (12)
C320.0289 (16)0.0345 (18)0.0202 (15)0.0019 (14)0.0016 (12)0.0014 (12)
C330.0320 (17)0.048 (2)0.0223 (16)0.0113 (15)0.0063 (12)0.0003 (14)
C340.0311 (17)0.048 (2)0.0260 (17)0.0194 (15)0.0070 (13)0.0046 (14)
C350.0200 (14)0.0246 (16)0.0183 (14)0.0065 (12)0.0012 (11)0.0007 (11)
C360.0267 (15)0.0276 (17)0.0250 (16)0.0047 (13)0.0058 (12)0.0038 (12)
C370.0268 (15)0.0249 (16)0.0299 (17)0.0029 (13)0.0054 (12)0.0026 (12)
C380.0191 (14)0.0269 (16)0.0238 (15)0.0006 (12)0.0000 (11)0.0058 (12)
C390.0201 (14)0.0267 (16)0.0207 (14)0.0006 (12)0.0004 (11)0.0017 (12)
C400.0194 (14)0.0238 (16)0.0236 (15)0.0007 (12)0.0010 (11)0.0003 (12)
C560.0315 (17)0.055 (2)0.0188 (16)0.0075 (16)0.0040 (12)0.0061 (14)
C570.0411 (19)0.058 (2)0.0182 (16)0.0153 (17)0.0023 (13)0.0070 (14)
C580.051 (2)0.055 (2)0.0209 (17)0.0154 (18)0.0092 (14)0.0115 (15)
O410.0397 (13)0.0418 (14)0.0435 (14)0.0011 (11)0.0088 (10)0.0051 (11)
O420.0471 (14)0.0436 (15)0.0571 (16)0.0022 (12)0.0099 (11)0.0111 (12)
O430.0591 (16)0.0386 (14)0.0471 (15)0.0102 (12)0.0034 (12)0.0045 (11)
C410.0356 (19)0.047 (2)0.039 (2)0.0022 (16)0.0001 (15)0.0040 (16)
C420.064 (2)0.037 (2)0.041 (2)0.0001 (18)0.0180 (17)0.0022 (15)
C430.0362 (18)0.041 (2)0.0378 (19)0.0004 (16)0.0049 (14)0.0029 (15)
C440.0406 (19)0.053 (2)0.040 (2)0.0023 (17)0.0086 (15)0.0059 (17)
C450.049 (2)0.053 (3)0.058 (3)0.012 (2)0.0105 (18)0.0118 (19)
C460.080 (3)0.040 (2)0.045 (2)0.009 (2)0.0156 (19)0.0022 (17)
C470.0361 (19)0.051 (2)0.051 (2)0.0009 (17)0.0007 (16)0.0005 (17)
C480.053 (2)0.058 (3)0.040 (2)0.0099 (19)0.0065 (17)0.0012 (18)
C490.052 (2)0.039 (2)0.046 (2)0.0055 (18)0.0035 (16)0.0034 (17)
C500.0393 (19)0.036 (2)0.042 (2)0.0022 (15)0.0063 (15)0.0017 (15)
C510.049 (2)0.048 (2)0.046 (2)0.0012 (18)0.0072 (17)0.0008 (17)
C520.044 (2)0.044 (2)0.047 (2)0.0001 (17)0.0059 (16)0.0026 (17)
Geometric parameters (Å, º) top
S11—O111.4361 (19)C29—C301.386 (3)
S11—O121.4359 (19)C29—H290.9500
S11—N111.650 (2)C30—H300.9500
S11—C151.747 (3)C32—C331.384 (4)
S21—O211.4358 (19)C32—C581.495 (4)
S21—O221.4417 (19)C33—C341.370 (4)
S21—N211.646 (2)C33—H330.9500
S21—C251.738 (3)C34—H340.9500
S31—O311.4346 (19)C35—C361.393 (4)
S31—O321.440 (2)C35—C401.394 (3)
S31—N311.648 (2)C36—C371.378 (3)
S31—C351.748 (2)C36—H360.9500
N11—C111.390 (3)C37—C381.403 (3)
N11—H110.8800C37—H370.9500
N12—C111.334 (3)C38—C391.404 (4)
N12—C121.348 (3)C39—C401.372 (3)
N13—C111.333 (3)C39—H390.9500
N13—C141.337 (3)C40—H400.9500
N14—C181.365 (3)C56—H56A0.9800
N14—H14A0.8800C56—H56B0.9800
N14—H14B0.8800C56—H56C0.9800
N21—C211.378 (3)C57—H57A0.9800
N21—H210.8800C57—H57B0.9800
N22—C211.336 (3)C57—H57C0.9800
N22—C221.336 (3)C58—H58A0.9800
N23—C241.339 (3)C58—H58B0.9800
N23—C211.339 (3)C58—H58C0.9800
N24—C281.366 (3)O41—C411.433 (3)
N24—H24A0.8800O41—C441.433 (4)
N24—H24B0.8800O42—C481.422 (4)
N31—C311.386 (3)O42—C451.430 (4)
N31—H310.8800O43—C521.419 (3)
N32—C311.337 (3)O43—C491.429 (4)
N32—C321.346 (3)C41—C421.515 (4)
N33—C341.336 (3)C41—H41A0.9900
N33—C311.339 (3)C41—H41B0.9900
N34—C381.373 (3)C42—C431.532 (4)
N34—H34A0.8800C42—H42A0.9900
N34—H34B0.8800C42—H42B0.9900
C12—C131.378 (4)C43—C441.520 (4)
C12—C561.499 (3)C43—H43A0.9900
C13—C141.378 (4)C43—H43B0.9900
C13—H130.9500C44—H44A0.9900
C14—H140.9500C44—H44B0.9900
C15—C161.394 (4)C45—C461.511 (5)
C15—C201.395 (3)C45—H45A0.9900
C16—C171.379 (3)C45—H45B0.9900
C16—H160.9500C46—C471.518 (4)
C17—C181.405 (4)C46—H46A0.9900
C17—H170.9500C46—H46B0.9900
C18—C191.401 (4)C47—C481.496 (4)
C19—C201.372 (3)C47—H47A0.9900
C19—H190.9500C47—H47B0.9900
C20—H200.9500C48—H48A0.9900
C22—C231.382 (4)C48—H48B0.9900
C22—C571.500 (3)C49—C501.521 (4)
C23—C241.379 (3)C49—H49A0.9900
C23—H230.9500C49—H49B0.9900
C24—H240.9500C50—C511.522 (4)
C25—C301.387 (4)C50—H50A0.9900
C25—C261.398 (3)C50—H50B0.9900
C26—C271.378 (3)C51—C521.504 (4)
C26—H260.9500C51—H51A0.9900
C27—C281.403 (4)C51—H51B0.9900
C27—H270.9500C52—H52A0.9900
C28—C291.407 (4)C52—H52B0.9900
O11—S11—O12118.25 (11)C33—C34—H34118.7
O11—S11—N11109.77 (12)C36—C35—C40120.5 (2)
O12—S11—N11102.86 (11)C36—C35—S31119.7 (2)
O12—S11—C15110.37 (12)C40—C35—S31119.7 (2)
O11—S11—C15107.49 (12)C37—C36—C35119.5 (3)
N11—S11—C15107.65 (12)C37—C36—H36120.3
O21—S21—O22118.40 (11)C35—C36—H36120.3
O21—S21—N21109.83 (12)C36—C37—C38120.8 (3)
O22—S21—N21102.72 (11)C36—C37—H37119.6
O21—S21—C25107.90 (12)C38—C37—H37119.6
O22—S21—C25110.03 (12)N34—C38—C37121.3 (3)
N21—S21—C25107.43 (12)N34—C38—C39120.0 (2)
O31—S31—O32118.81 (12)C37—C38—C39118.7 (2)
O31—S31—N31102.59 (11)C40—C39—C38120.7 (2)
O32—S31—N31109.65 (12)C40—C39—H39119.7
O31—S31—C35110.23 (12)C38—C39—H39119.7
O32—S31—C35107.49 (12)C39—C40—C35119.8 (3)
N31—S31—C35107.56 (12)C39—C40—H40120.1
C11—N11—S11125.00 (17)C35—C40—H40120.1
C11—N11—H11117.5C12—C56—H56A109.5
S11—N11—H11117.5C12—C56—H56B109.5
C11—N12—C12116.0 (2)H56A—C56—H56B109.5
C11—N13—C14114.9 (2)C12—C56—H56C109.5
C18—N14—H14A120.0H56A—C56—H56C109.5
C18—N14—H14B120.0H56B—C56—H56C109.5
H14A—N14—H14B120.0C22—C57—H57A109.5
C21—N21—S21125.26 (17)C22—C57—H57B109.5
C21—N21—H21117.4H57A—C57—H57B109.5
S21—N21—H21117.4C22—C57—H57C109.5
C21—N22—C22116.3 (2)H57A—C57—H57C109.5
C24—N23—C21115.2 (2)H57B—C57—H57C109.5
C28—N24—H24A120.0C32—C58—H58A109.5
C28—N24—H24B120.0C32—C58—H58B109.5
H24A—N24—H24B120.0H58A—C58—H58B109.5
C31—N31—S31125.66 (18)C32—C58—H58C109.5
C31—N31—H31117.2H58A—C58—H58C109.5
S31—N31—H31117.2H58B—C58—H58C109.5
C31—N32—C32116.0 (2)C41—O41—C44104.6 (2)
C34—N33—C31115.1 (2)C48—O42—C45104.3 (2)
C38—N34—H34A120.0C52—O43—C49105.2 (2)
C38—N34—H34B120.0O41—C41—C42105.4 (2)
H34A—N34—H34B120.0O41—C41—H41A110.7
N12—C11—N13127.5 (2)C42—C41—H41A110.7
N13—C11—N11115.4 (2)O41—C41—H41B110.7
N12—C11—N11117.1 (2)C42—C41—H41B110.7
N12—C12—C13121.4 (2)H41A—C41—H41B108.8
N12—C12—C56115.1 (2)C41—C42—C43104.4 (3)
C13—C12—C56123.5 (3)C41—C42—H42A110.9
C14—C13—C12117.2 (3)C43—C42—H42A110.9
C14—C13—H13121.4C41—C42—H42B110.9
C12—C13—H13121.4C43—C42—H42B110.9
N13—C14—C13123.0 (3)H42A—C42—H42B108.9
N13—C14—H14118.5C44—C43—C42103.7 (3)
C13—C14—H14118.5C44—C43—H43A111.0
C16—C15—C20120.3 (2)C42—C43—H43A111.0
C16—C15—S11120.2 (2)C44—C43—H43B111.0
C20—C15—S11119.5 (2)C42—C43—H43B111.0
C17—C16—C15119.6 (2)H43A—C43—H43B109.0
C17—C16—H16120.2O41—C44—C43105.9 (3)
C15—C16—H16120.2O41—C44—H44A110.6
C16—C17—C18120.8 (3)C43—C44—H44A110.6
C16—C17—H17119.6O41—C44—H44B110.6
C18—C17—H17119.6C43—C44—H44B110.6
N14—C18—C19120.4 (2)H44A—C44—H44B108.7
N14—C18—C17121.1 (3)O42—C45—C46106.8 (3)
C19—C18—C17118.4 (2)O42—C45—H45A110.4
C20—C19—C18121.1 (2)C46—C45—H45A110.4
C20—C19—H19119.5O42—C45—H45B110.4
C18—C19—H19119.5C46—C45—H45B110.4
C19—C20—C15119.8 (3)H45A—C45—H45B108.6
C19—C20—H20120.1C45—C46—C47104.0 (3)
C15—C20—H20120.1C45—C46—H46A110.9
N22—C21—N23127.0 (2)C47—C46—H46A110.9
N22—C21—N21117.6 (2)C45—C46—H46B110.9
N23—C21—N21115.4 (2)C47—C46—H46B110.9
N22—C22—C23121.4 (2)H46A—C46—H46B109.0
N22—C22—C57115.8 (2)C48—C47—C46103.6 (3)
C23—C22—C57122.8 (3)C48—C47—H47A111.0
C24—C23—C22117.5 (3)C46—C47—H47A111.0
C24—C23—H23121.3C48—C47—H47B111.0
C22—C23—H23121.3C46—C47—H47B111.0
N23—C24—C23122.5 (3)H47A—C47—H47B109.0
N23—C24—H24118.8O42—C48—C47105.2 (3)
C23—C24—H24118.8O42—C48—H48A110.7
C30—C25—C26120.0 (2)C47—C48—H48A110.7
C30—C25—S21120.3 (2)O42—C48—H48B110.7
C26—C25—S21119.7 (2)C47—C48—H48B110.7
C27—C26—C25120.2 (3)H48A—C48—H48B108.8
C27—C26—H26119.9O43—C49—C50106.2 (2)
C25—C26—H26119.9O43—C49—H49A110.5
C26—C27—C28120.4 (2)C50—C49—H49A110.5
C26—C27—H27119.8O43—C49—H49B110.5
C28—C27—H27119.8C50—C49—H49B110.5
N24—C28—C27120.6 (3)H49A—C49—H49B108.7
N24—C28—C29120.5 (3)C49—C50—C51103.5 (3)
C27—C28—C29118.9 (2)C49—C50—H50A111.1
C30—C29—C28120.3 (3)C51—C50—H50A111.1
C30—C29—H29119.8C49—C50—H50B111.1
C28—C29—H29119.8C51—C50—H50B111.1
C29—C30—C25120.1 (2)H50A—C50—H50B109.0
C29—C30—H30120.0C52—C51—C50104.4 (2)
C25—C30—H30120.0C52—C51—H51A110.9
N32—C31—N33127.3 (2)C50—C51—H51A110.9
N32—C31—N31117.5 (2)C52—C51—H51B110.9
N33—C31—N31115.2 (2)C50—C51—H51B110.9
N32—C32—C33121.0 (3)H51A—C51—H51B108.9
N32—C32—C58115.5 (2)O43—C52—C51104.5 (3)
C33—C32—C58123.6 (3)O43—C52—H52A110.9
C34—C33—C32117.9 (3)C51—C52—H52A110.9
C34—C33—H33121.0O43—C52—H52B110.9
C32—C33—H33121.0C51—C52—H52B110.9
N33—C34—C33122.7 (3)H52A—C52—H52B108.9
N33—C34—H34118.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N14—H14B···O320.882.112.968 (3)166
N14—H14A···O410.882.403.051 (3)131
N24—H24A···O420.882.292.998 (3)137
N34—H34B···O430.882.302.983 (3)134
N11—H11···N23i0.882.042.913 (3)169
N21—H21···N13ii0.882.002.873 (3)172
N24—H24B···O21iii0.882.172.999 (3)158
N31—H31···N33iv0.882.022.893 (3)174
N34—H34A···O11v0.882.153.009 (3)167
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y1/2, z+3/2; (iv) x+2, y+2, z+2; (v) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N14—H14B···O320.882.112.968 (3)166
N14—H14A···O410.882.403.051 (3)131
N24—H24A···O420.882.292.998 (3)137
N34—H34B···O430.882.302.983 (3)134
N11—H11···N23i0.882.042.913 (3)169
N21—H21···N13ii0.882.002.873 (3)172
N24—H24B···O21iii0.882.172.999 (3)158
N31—H31···N33iv0.882.022.893 (3)174
N34—H34A···O11v0.882.153.009 (3)167
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y1/2, z+3/2; (iv) x+2, y+2, z+2; (v) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC11H12N4O2S·C4H8O
Mr336.41
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)10.5765 (2), 11.8088 (2), 39.1512 (7)
β (°) 92.618 (1)
V3)4884.71 (15)
Z12
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.25 × 0.22 × 0.20
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.947, 0.957
No. of measured, independent and
observed [I > 2σ(I)] reflections
26393, 10636, 6070
Rint0.119
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.169, 1.01
No. of reflections10636
No. of parameters625
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.58

Computer programs: COLLECT (Hooft, 1998; Nonius, 2004), (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012).

 

Acknowledgements

The author acknowledges the School of Chemistry, Cardiff University, Wales, for the data collection.

References

First citationAcharya, K. R., Kuchela, K. N. & Kartha, G. (1982). J. Crystallogr. Spectrosc. Res. 12, 369–376.  CAS Google Scholar
First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationCaria, M. R. & Mohamed, R. (1992). Acta Cryst. B48, 492–498.  CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationHooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationHossain, G. M. G. (2006). Acta Cryst. E62, o2166–o2167.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationNonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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