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In the title compound, C8H8N2OS, strong intramolecular N—H...O hydrogen bonds [N...O = 2.669 (3) and 2.618 (3) Å] form almost planar six-membered rings and enforce the conformation of the mol­ecule. Two kinds of intermolecular N—H...S hydrogen bonds [N...S = 3.309 (3)–3.456 (2) Å] between two symmetry-independent mol­ecules form consecutive dimers that expand in ribbons along the [100] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103001161/gg1152sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103001161/gg1152Isup2.hkl
Contains datablock I

CCDC reference: 205313

Comment top

Thiourea derivatives can be regarded as model compounds for different intra- and intermolecular interactions involving S atoms. In the literature, there are only a few structural reports describing these compounds, perhaps due to the reported difficulties in preparing crystals for X-ray diffraction studies (Shanmuga Sundara Raj et al., 1999). Therefore, we have carried out the X-ray structural study of a simple thiourea derivative, N-benzoyl-thiourea, (I). Our main goal of this study was to identify the patterns created by the intermolecular N—H···S interactions. \sch

The asymmetric part of the unit cell of (I) contains two molecules, hereinafter referred to as molecules A and B. The bond lengths and angles of these symmetry-independent molecules are quite similar. The normal probability plot analysis (Abrahams & Keve, 1971; International Tables for X-ray Crystallography, 1974, Vol. IV, pp. 293–309) shows that the differences are of a statistical rather than systematic nature; the correlation coefficients between experimental and theoretical distributions are 0.97 for bond lengths and 0.94 for bond angles. In fact, there is an approximate pseudo centre of symmetry between molecules A and B. Taking into account only C—CO-thiourea fragments, the coordinates of this pseudo centre are 0.704 (6), 0.78 (2), 0.502 (7). The phenyl rings deviate considerably from this approximate symmetry, the dihedral angle between the least-squares plane of the ring and the plane through the three atoms C11, O11, N11 being 42.9 (1)° in molecule A and 33.0 (1)° in B.

The C1/C11/O11/N11 and thiourea fragments are almost ideally planar, with the maximum deviations from the least-squares planes not exceeding 0.012 (2) Å. The dihedral angles between these planes are also small: 7.3 (1)° in A and 2.1 (2)° in B. This almost coplanar conformation is enforced by a strong intramolecular N12—H···O11 hydrogen bond that closes an almost planar six-membered ring [maximum deviations of 0.051 (6) and 0.015 (8) Å for molecules A and B, respectively]. The significantly more folded conformation of molecule A correlates well with the lengths of the intramolecular hydrogen bonds (Table 2). A similar conformation was found in a closely related compound, N-(4-methylbenzoyl)thiourea, (II) (Reinke, 2001). In that compound, the dihedral angle between two planar fragments is 5.8°, and the hydrogen bonds also have an intermediate length, with an N···O distance of 2.640 Å. Additional arguments for the decisive role of this hydrogen bond in the determination of molecular conformation can be obtained by an examination of the May 2002 release of the Cambridge Structural Database (Allen, 2002). For 28 fragments with primary and secondary N12 groups, the mean value of the improper OC···CN torsion angle is 3(2)° [for (I), this angle is 7.0 (2)° in molecule A and 1.0 (2)° in molecule B, while for (II), it is 3.5°], while for 26 compounds with tertiary groups, the mean value of this angle is 51 (7)° (after removal of two outliers).

The pattern of bond lengths and angles in (I) is quite typical. Both CO and CS bonds have double-bond character, and the C—N bonds in the thiourea fragment are significantly different. The C—NH2 bond is remarkably short, and it is one of the shortest C—N bonds found in thiourea derivatives.

The crystal packing in (I) is governed by two kinds of strong N—H···S hydrogen bonds (Table 2, Fig. 1) which form pseudo-centrosymmetric dimers of molecules A and B. These hydrogen bonds connect the molecules into ribbons along the [100] direction. These hydrophilic hydrogen-bonded channels are surrounded by the hydrophobic surface of the phenyl rings. Interestingly, the true centre of symmetry is not utilized in creating of the main structural pattern; instead, the structure uses two different molecules connected by approximate centres of symmetry. The molecule of (II) also crystallizes in the triclinic space group P1, but with Z = 2, and a similar packing is created by means of exact centres of symmetry. However, in this case, one of the N—H···S intermolecular hydrogen bonds is much longer than the other (3.711 Å).

Experimental top

N-benzoylthiourea was prepared by a modification of the method previously described by Klayman et al. (1972). Benzoyl chloride was added to a solution of potassium thiocyanate in warm anhydrous acetone, and the resulting mixture was refluxed. Potassium chloride, which precipitated as a fine powder, was removed by filtration and a concentrated aqueous ammonia solution was added to the filtrate. The resulting mixture was evaporated to dryness using a rotatory evaporator and the residue was extracted with ethanol. Colourless crystals of (I) were obtained by slow evaporation from a methanol solution.

Computing details top

Data collection: KM-4 Software (Kuma Diffraction, 1992); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989).

Figures top
[Figure 1] Fig. 1. A fragment of the hydrogen-bonded ribbon of molecules A and B of (I), together with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level, H atoms are shown as small spheres of arbitrary radii and hydrogen bonds are drawn with dashed lines [symmetry code: (i) 1 + x, y, z].
1-benzoylthiourea top
Crystal data top
C8H8N2OSZ = 4
Mr = 180.22F(000) = 376
Triclinic, P1Dx = 1.365 Mg m3
Hall symbol: -p-1Mo Kα radiation, λ = 0.71073 Å
a = 8.2300 (16) ÅCell parameters from 25 reflections
b = 9.3410 (18) Åθ = 5–26°
c = 12.594 (3) ŵ = 0.32 mm1
α = 73.91 (3)°T = 293 K
β = 88.14 (3)°Plate, colourless
γ = 70.80 (3)°0.30 × 0.15 × 0.10 mm
V = 876.7 (4) Å3
Data collection top
Kuma KM-4 four-circle
diffractometer
Rint = 0.025
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 2.5°
Graphite monochromatorh = 99
ω/2θ scansk = 010
3276 measured reflectionsl = 1414
3067 independent reflections3 standard reflections every 100 reflections
1929 reflections with I > 2σ(I) intensity decay: 3%
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)] = 0.034All H-atom parameters refined
wR(F2) = 0.071 w = 1/[σ2(Fo2) + (0.01P)2 + 0.3P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.009
3067 reflectionsΔρmax = 0.15 e Å3
282 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (2)
Crystal data top
C8H8N2OSγ = 70.80 (3)°
Mr = 180.22V = 876.7 (4) Å3
Triclinic, P1Z = 4
a = 8.2300 (16) ÅMo Kα radiation
b = 9.3410 (18) ŵ = 0.32 mm1
c = 12.594 (3) ÅT = 293 K
α = 73.91 (3)°0.30 × 0.15 × 0.10 mm
β = 88.14 (3)°
Data collection top
Kuma KM-4 four-circle
diffractometer
Rint = 0.025
3276 measured reflections3 standard reflections every 100 reflections
3067 independent reflections intensity decay: 3%
1929 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.071All H-atom parameters refined
S = 1.00Δρmax = 0.15 e Å3
3067 reflectionsΔρmin = 0.21 e Å3
282 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.7198 (3)0.8666 (3)0.79040 (16)0.0461 (5)
C2A0.7341 (4)0.9887 (3)0.8263 (2)0.0648 (7)
H2A0.643 (4)1.084 (3)0.814 (2)0.096 (10)*
C3A0.8884 (4)0.9755 (4)0.8743 (2)0.0774 (8)
H3A0.901 (3)1.057 (3)0.895 (2)0.083 (9)*
C4A1.0266 (4)0.8403 (4)0.8887 (2)0.0782 (9)
H4A1.130 (4)0.834 (3)0.928 (2)0.094 (9)*
C5A1.0118 (4)0.7171 (4)0.8566 (2)0.0792 (9)
H5A1.100 (3)0.623 (3)0.8720 (19)0.076 (8)*
C6A0.8586 (3)0.7293 (3)0.80687 (19)0.0614 (7)
H6A0.847 (3)0.649 (3)0.7871 (18)0.065 (8)*
C11A0.5498 (3)0.8855 (3)0.74004 (17)0.0484 (5)
O11A0.4140 (2)0.9440 (2)0.77829 (13)0.0666 (5)
N11A0.5567 (2)0.8304 (2)0.64877 (15)0.0463 (5)
H11A0.646 (3)0.813 (2)0.6214 (16)0.038 (6)*
C12A0.4222 (3)0.8226 (2)0.59098 (16)0.0456 (5)
S12A0.46386 (8)0.75591 (9)0.47884 (5)0.0619 (2)
S12B0.95337 (7)0.73710 (9)0.54810 (5)0.0612 (2)
N12A0.2691 (3)0.8617 (3)0.62850 (19)0.0597 (6)
H1210.258 (3)0.894 (3)0.6792 (18)0.053 (8)*
H1220.180 (4)0.843 (3)0.598 (2)0.087 (9)*
C1B0.7081 (3)0.6561 (3)0.21436 (17)0.0461 (5)
C2B0.6660 (3)0.7133 (3)0.10126 (19)0.0634 (7)
H2B0.730 (3)0.772 (3)0.0563 (19)0.077 (8)*
C3B0.5285 (4)0.6890 (4)0.0574 (2)0.0719 (8)
H3B0.498 (3)0.732 (3)0.016 (2)0.077 (8)*
C4B0.4341 (3)0.6103 (3)0.1238 (2)0.0654 (7)
H4B0.339 (3)0.595 (3)0.094 (2)0.083 (8)*
C5B0.4767 (3)0.5513 (3)0.2361 (2)0.0558 (6)
H5B0.417 (3)0.496 (3)0.2832 (18)0.064 (7)*
C6B0.6134 (3)0.5743 (3)0.28104 (19)0.0483 (6)
H6B0.639 (3)0.534 (2)0.3554 (17)0.054 (6)*
C11B0.8600 (3)0.6803 (3)0.25664 (18)0.0521 (6)
O11B0.9836 (2)0.6829 (3)0.20079 (13)0.0811 (6)
N11B0.8552 (2)0.7006 (2)0.36139 (14)0.0473 (5)
H11B0.760 (2)0.700 (2)0.3895 (15)0.036 (5)*
C12B0.9821 (3)0.7191 (3)0.41926 (17)0.0504 (6)
N12B1.1223 (3)0.7217 (4)0.3704 (2)0.0963 (10)
H1231.205 (3)0.723 (3)0.405 (2)0.082 (9)*
H1241.127 (4)0.706 (3)0.308 (2)0.095 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0489 (13)0.0522 (14)0.0391 (11)0.0170 (11)0.0017 (9)0.0158 (10)
C2A0.0671 (18)0.0581 (17)0.0679 (16)0.0155 (15)0.0178 (13)0.0198 (14)
C3A0.087 (2)0.078 (2)0.0769 (19)0.0354 (19)0.0205 (15)0.0250 (16)
C4A0.0593 (18)0.116 (3)0.0621 (17)0.0257 (19)0.0109 (13)0.0328 (17)
C5A0.0577 (18)0.100 (2)0.0688 (18)0.0055 (17)0.0132 (14)0.0423 (18)
C6A0.0634 (16)0.0638 (18)0.0548 (15)0.0070 (14)0.0070 (12)0.0291 (13)
C11A0.0514 (14)0.0481 (14)0.0472 (13)0.0170 (11)0.0008 (10)0.0149 (11)
O11A0.0513 (10)0.0865 (13)0.0694 (11)0.0167 (9)0.0060 (8)0.0414 (10)
N11A0.0410 (11)0.0580 (13)0.0478 (11)0.0210 (10)0.0038 (9)0.0221 (9)
C12A0.0438 (13)0.0469 (14)0.0456 (12)0.0186 (11)0.0003 (10)0.0079 (10)
S12A0.0506 (4)0.1030 (6)0.0498 (4)0.0390 (4)0.0057 (3)0.0332 (4)
S12B0.0452 (4)0.0976 (5)0.0504 (4)0.0282 (3)0.0009 (3)0.0307 (3)
N12A0.0433 (13)0.0795 (16)0.0637 (14)0.0184 (11)0.0015 (11)0.0341 (13)
C1B0.0442 (12)0.0514 (14)0.0446 (12)0.0129 (11)0.0013 (10)0.0201 (11)
C2B0.0644 (16)0.089 (2)0.0448 (13)0.0339 (15)0.0059 (12)0.0214 (13)
C3B0.0717 (18)0.105 (2)0.0434 (15)0.0340 (17)0.0079 (13)0.0211 (15)
C4B0.0605 (17)0.0751 (19)0.0693 (18)0.0247 (15)0.0120 (14)0.0295 (15)
C5B0.0579 (15)0.0496 (15)0.0632 (16)0.0222 (13)0.0021 (12)0.0152 (13)
C6B0.0515 (14)0.0466 (14)0.0465 (13)0.0136 (11)0.0032 (11)0.0152 (11)
C11B0.0475 (13)0.0654 (16)0.0487 (13)0.0207 (12)0.0034 (11)0.0219 (12)
O11B0.0612 (11)0.1485 (18)0.0625 (11)0.0562 (12)0.0212 (9)0.0515 (11)
N11B0.0353 (10)0.0659 (13)0.0459 (11)0.0186 (9)0.0042 (8)0.0220 (9)
C12B0.0386 (13)0.0667 (16)0.0487 (13)0.0191 (11)0.0004 (10)0.0187 (12)
N12B0.0617 (16)0.200 (3)0.0664 (16)0.0758 (18)0.0179 (13)0.0619 (19)
Geometric parameters (Å, º) top
S12A—C12A1.678 (2)C5A—H5A0.91 (2)
O11A—C11A1.220 (2)C6A—H6A0.89 (2)
N11A—C11A1.376 (3)N11A—H11A0.791 (19)
N11A—C12A1.377 (3)N12A—H1210.77 (2)
N12A—C12A1.303 (3)N12A—H1220.93 (3)
S12B—C12B1.679 (2)C1B—C6B1.375 (3)
O11B—C11B1.220 (3)C1B—C2B1.387 (3)
N11B—C11B1.382 (3)C1B—C11B1.481 (3)
N11B—C12B1.374 (3)C2B—C3B1.384 (3)
N12B—C12B1.295 (3)C2B—H2B0.95 (2)
C1A—C6A1.377 (3)C3B—C4B1.356 (4)
C1A—C2A1.378 (3)C3B—H3B0.91 (2)
C1A—C11A1.491 (3)C4B—C5B1.379 (3)
C2A—C3A1.377 (4)C4B—H4B0.95 (3)
C2A—H2A0.94 (3)C5B—C6B1.378 (3)
C3A—C4A1.365 (4)C5B—H5B0.92 (2)
C3A—H3A0.90 (3)C6B—H6B0.91 (2)
C4A—C5A1.362 (4)N11B—H11B0.850 (19)
C4A—H4A0.98 (3)N12B—H1230.83 (3)
C5A—C6A1.383 (4)N12B—H1240.84 (3)
S12A—C12A—N11A118.70 (17)C12A—N11A—H11A116.0 (15)
S12A—C12A—N12A122.97 (18)C12A—N12A—H121118.0 (17)
N11A—C12A—N12A118.3 (2)C12A—N12A—H122120.2 (16)
C11A—N11A—C12A128.0 (2)H121—N12A—H122122 (2)
S12B—C12B—N11B120.50 (16)C6B—C1B—C2B119.2 (2)
S12B—C12B—N12B122.19 (18)C6B—C1B—C11B123.09 (19)
N11B—C12B—N12B117.3 (2)C2B—C1B—C11B117.6 (2)
C11B—N11B—C12B127.72 (19)C3B—C2B—C1B119.8 (3)
C6A—C1A—C2A119.5 (2)C3B—C2B—H2B121.7 (15)
C6A—C1A—C11A122.3 (2)C1B—C2B—H2B118.5 (15)
C2A—C1A—C11A118.2 (2)C4B—C3B—C2B120.7 (2)
C3A—C2A—C1A120.0 (3)C4B—C3B—H3B119.9 (16)
C3A—C2A—H2A118.8 (17)C2B—C3B—H3B119.3 (16)
C1A—C2A—H2A121.0 (17)C3B—C4B—C5B119.8 (2)
C4A—C3A—C2A120.3 (3)C3B—C4B—H4B120.5 (15)
C4A—C3A—H3A118.9 (17)C5B—C4B—H4B119.7 (15)
C2A—C3A—H3A120.8 (17)C6B—C5B—C4B120.1 (3)
C3A—C4A—C5A120.0 (3)C6B—C5B—H5B117.9 (14)
C3A—C4A—H4A116.8 (16)C4B—C5B—H5B122.0 (14)
C5A—C4A—H4A123.0 (16)C1B—C6B—C5B120.4 (2)
C4A—C5A—C6A120.4 (3)C1B—C6B—H6B121.1 (13)
C4A—C5A—H5A120.7 (16)C5B—C6B—H6B118.6 (13)
C6A—C5A—H5A118.7 (16)O11B—C11B—N11B121.6 (2)
C1A—C6A—C5A119.7 (3)O11B—C11B—C1B121.20 (19)
C1A—C6A—H6A119.1 (15)N11B—C11B—C1B117.18 (19)
C5A—C6A—H6A121.2 (15)C12B—N11B—H11B120.7 (13)
O11A—C11A—N11A122.4 (2)C11B—N11B—H11B111.5 (13)
O11A—C11A—C1A122.10 (19)C12B—N12B—H123119.5 (18)
N11A—C11A—C1A115.54 (19)C12B—N12B—H124115 (2)
C11A—N11A—H11A115.4 (15)H123—N12B—H124124 (3)
C6A—C1A—C11A—O11A135.1 (2)C11B—C1B—C2B—C3B177.9 (2)
C6B—C1B—C11B—O11B145.3 (2)C1B—C2B—C3B—C4B0.2 (4)
C6A—C1A—C2A—C3A2.6 (4)C2B—C3B—C4B—C5B1.0 (4)
C11A—C1A—C2A—C3A179.4 (2)C3B—C4B—C5B—C6B0.9 (4)
C1A—C2A—C3A—C4A1.5 (4)C2B—C1B—C6B—C5B0.9 (3)
C2A—C3A—C4A—C5A0.6 (5)C11B—C1B—C6B—C5B177.8 (2)
C3A—C4A—C5A—C6A1.6 (5)C4B—C5B—C6B—C1B0.0 (4)
C2A—C1A—C6A—C5A1.7 (4)C2B—C1B—C11B—O11B31.7 (4)
C11A—C1A—C6A—C5A178.3 (2)C6B—C1B—C11B—N11B35.1 (3)
C4A—C5A—C6A—C1A0.4 (4)C2B—C1B—C11B—N11B147.9 (2)
C2A—C1A—C11A—O11A41.6 (3)O11B—C11B—N11B—C12B2.9 (4)
C6A—C1A—C11A—N11A43.9 (3)C1B—C11B—N11B—C12B177.4 (2)
C2A—C1A—C11A—N11A139.4 (2)C11B—N11B—C12B—N12B1.8 (4)
O11A—C11A—N11A—C12A4.0 (4)C11B—N11B—C12B—S12B178.20 (19)
C1A—C11A—N11A—C12A175.1 (2)O11A—C11A—C12A—S12A173.4 (2)
C11A—N11A—C12A—N12A4.7 (3)O11A—C11A—C12A—N12A7.5 (2)
C11A—N11A—C12A—S12A177.85 (18)O11B—C11B—C12B—S12B179.7 (2)
C6B—C1B—C2B—C3B0.8 (4)O11B—C11B—C12B—N12B0.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11A—H11A···S12B0.791 (19)2.60 (2)3.391 (2)175.0 (19)
N12A—H121···O11A0.77 (2)2.06 (2)2.669 (3)136 (2)
N11B—H11B···S12A0.850 (19)2.606 (19)3.442 (2)168.2 (17)
N12B—H124···O11B0.84 (3)1.92 (3)2.618 (3)140 (3)
N12B—H123···S12Ai0.83 (3)2.49 (3)3.309 (3)170 (2)
N12A—H122···S12Bii0.93 (3)2.55 (3)3.456 (2)167 (2)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC8H8N2OS
Mr180.22
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.2300 (16), 9.3410 (18), 12.594 (3)
α, β, γ (°)73.91 (3), 88.14 (3), 70.80 (3)
V3)876.7 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.32
Crystal size (mm)0.30 × 0.15 × 0.10
Data collection
DiffractometerKuma KM-4 four-circle
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3276, 3067, 1929
Rint0.025
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.071, 1.00
No. of reflections3067
No. of parameters282
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.15, 0.21

Computer programs: KM-4 Software (Kuma Diffraction, 1992), KM-4 Software, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), Stereochemical Workstation Operation Manual (Siemens, 1989).

Selected geometric parameters (Å, º) top
S12A—C12A1.678 (2)S12B—C12B1.679 (2)
O11A—C11A1.220 (2)O11B—C11B1.220 (3)
N11A—C11A1.376 (3)N11B—C11B1.382 (3)
N11A—C12A1.377 (3)N11B—C12B1.374 (3)
N12A—C12A1.303 (3)N12B—C12B1.295 (3)
S12A—C12A—N11A118.70 (17)S12B—C12B—N11B120.50 (16)
S12A—C12A—N12A122.97 (18)S12B—C12B—N12B122.19 (18)
N11A—C12A—N12A118.3 (2)N11B—C12B—N12B117.3 (2)
C11A—N11A—C12A128.0 (2)C11B—N11B—C12B127.72 (19)
C6A—C1A—C11A—O11A135.1 (2)C6B—C1B—C11B—O11B145.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11A—H11A···S12B0.791 (19)2.60 (2)3.391 (2)175.0 (19)
N12A—H121···O11A0.77 (2)2.06 (2)2.669 (3)136 (2)
N11B—H11B···S12A0.850 (19)2.606 (19)3.442 (2)168.2 (17)
N12B—H124···O11B0.84 (3)1.92 (3)2.618 (3)140 (3)
N12B—H123···S12Ai0.83 (3)2.49 (3)3.309 (3)170 (2)
N12A—H122···S12Bii0.93 (3)2.55 (3)3.456 (2)167 (2)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
 

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