Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616004861/eg3200sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004861/eg3200Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004861/eg3200IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004861/eg3200IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004861/eg3200IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004861/eg3200Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004861/eg3200VIsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004861/eg3200VIIsup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004861/eg3200VIIIsup9.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004861/eg3200Isup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004861/eg3200IIsup11.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004861/eg3200IIIsup12.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004861/eg3200IVsup13.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004861/eg3200Vsup14.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004861/eg3200VIsup15.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004861/eg3200VIIsup16.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616004861/eg3200VIIIsup17.cml |
CCDC references: 1470144; 1470143; 1470142; 1470141; 1470140; 1470139; 1470138; 1470137
One of the main targets of crystal engineering is to establish reliable intermolecular interaction motifs, so-called synthons, which are suitable for the design of new crystal structures of molecular compounds (Desiraju, 2007). Especially hydrogen bonds are one of the most used intermolecular interactions in crystal engineering due to their strength and directionality (Aakeröy, 1997). Among the hydrogen-bonded synthons, the R22(8) motif is of particular importance (Bernstein et al., 1995) as it is formed by a large number of functional groups, for example, by carboxy or amide groups (Blagden et al., 2007; Rodríguez-Cuamatzi et al., 2007). The three compounds 5-(hydroxymethyl)uracil (5HMU), 5-carboxyuracil (5CU) and 5-carboxy-2-thiouracil (5CTU) show various biologically important properties: 5HMU is one of the major oxidative modifications of thymine and might be used as a biomarker in order to estimate biologically effective levels of carcinogen exposure (Bianchini et al., 1998); 5CU exhibits antitumour, anti-HIV and antiepileptic activity (Ross et al., 1960; Lea et al., 1992; Nichol & Clegg, 2009); and 5CTU, as well as its derivatives, exhibits anticancer and antibacterial properties (Hueso-Urena & Moreno-Carretero, 1995). All three compounds are well suited for the formation of hydrogen-bonded networks within crystal and cocrystal structures since they all contain an ADA (A = acceptor and D = donor) and an AD site. In addition, they are capable of forming an intramolecular S(6) motif involving an O—H···O hydrogen bond between the OH group of the hydroxymethyl group (5HMU) or the carboxy group (5CU and 5CTU) and the carbonyl group at atom C4. The formation of this intramolecular hydrogen bond is possible only if atom C4 and the O atom of the hydroxy group adopt a synperiplanar arrangement (defined via the torsion angle ω). In the case of 5CU and 5CTU, this is important for the formation of R22(8) carboxy-carboxy dimers since the intramolecular hydrogen bonds would prevent the formation of intermolecular hydrogen bonds. A search of the Cambridge Structural Database (CSD, Version 5.37, November 2015; Groom & Allen, 2014) restricted to organic and not polymeric structures yielded no match for 5HMU, two hits for 5CU, namely 5-carboxyuracil monohydrate (CSD refcode AYEBIP; Law et al., 2004) and 4,4'-bipyridin-1-ium uracil-5-carboxylate–4,4'-bipyridine–5-carboxyuracil (2/1/4) (HOXHIM; Nichol & Clegg, 2009), and one hit for 5CTU, viz. 5-carboxy-2-thiouracil monohydrate (QEHSEB; Tiekink, 2001). In order to gain more information about the preferred hydrogen-bonding patterns of 5HMU, 5CU and 5CTU and to point out the preferred conformation of the residue bonded to atom C5 we performed crystallization experiments from different solvents yielding two solvent free structures, (I) and (VIII), as well as the six new solvates (II)–(VII).
Crystals of (I)–(VIII) were obtained by isothermal solvent evaporation experiments under different conditions from commercially available uracil derivatives and various solvents (Table 1). All solvents were applied without further purification and the crystallization experiments were performed at room temperature.
Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms, except those of the disordered solvent molecules, were located initially by difference Fourier synthesis. Carbon-bound H atoms were placed in calculated positions and refined using a riding model, with methyl C—H = 0.98 Å, secondary C—H = 0.99 Å and aromatic C—H = 0.95 Å, and with Uiso(H) = 1.5Ueq(C) for methyl or 1.2Ueq(C) for secondary and aromatic H atoms. Free rotation about the local threefold axis was allowed for all methyl groups except those of the minor-occupied sites of the disordered DMAC molecule in (IV) and the minor-occupied conformation of the rotationally disordered methyl group of the DMF molecule in (V). H atoms bonded to O atoms or N atoms were refined isotropically with the isotropic displacement parameters coupled to the equivalent isotropic displacement parameters of the parent N atoms or O atoms, with Uiso(H) = 1.2Ueq(N,O). Tentative free refinements of their positional coordinates resulted in an unsatisfactory wide range of D—H distances; bond lengths were therefore restrained to 0.88 (2) Å for N—H and to 0.84 (2) Å for O—H.
In (IV), the DMAC molecule is disordered over a pseudo-mirror plane along atoms O21X and C12X perpendicular to the molecular plane [site-occupancy factor for the major-occupied orientation = 0.644 (9)]. For the DMAC molecule, similarity restraints for the 1,2- and 1,3-distances were applied as well as the similar-ADP and the rigid-bond (Hirshfeld, 1976) restraints (SIMU and DELU in SHELXL2014; Sheldrick, 2015).
In (IV) [(V)?], the H atoms of the C11X methyl group of the DMF molecule show a rotational disorder [site-occupancy factor for the major-occupied conformation = 0.55 (3)].
5-(Hydroxymethyl)uracil, (I), crystallizes in the triclinic space group P1 with one planar molecule in the asymmetric unit (r.m.s deviation for all non-H atoms = 0.040 Å), whereby atoms C4A and O51A exhibit an antiperiplanar conformation [ω = 175.0 (2)°] (Fig. 1). In the packing, chains of 5HMU molecules are formed via R22(8) N—H···O hydrogen-bond motifs, which are extended to a two-dimensional network via R24(16) and R44(20) patterns involving further O—H···O hydrogen bonds (Fig. 2 and Table 3).
The DMF solvate of 5-carboxyuracil, (II), crystallizes in the monoclinic space group P21/c. The asymmetric unit consists of one planar 5CU molecule (A) and one DMF molecule (X) connected by an N—H···O hydrogen bond and enclosing a dihedral angle of 7.75 (14)° (r.m.s deviations for all non-H atoms = 0.047 Å for A and 0.009 Å for X). Atoms C4A and O52A adopt a synperiplanar conformation [ω = -3.0 (5)°] and an S(6) motif is formed via an O—H···O hydrogen bond (Fig. 3). In the packing, additional R22(9) patterns consisting of one N—H···O and one C—H···O hydrogen bond are formed between the 5CU molecules yielding chains running along the b axis whereby the DMF molecules are located at both sides of the chains (Fig. 4 and Table 4).
The DMSO solvate of 5-carboxyuracil, (III), crystallizes in the monoclinic space group P21/c with one planar 5CU molecule (A; r.m.s. deviation for all non-H atoms = 0.010 Å) and one DMSO molecule (X) in the asymmetric unit. Atoms C4A and O52A show a synperiplanar arrangement [ω = 0.4 (4)°] leading to the S(6) O—H···O motif and molecules A and X are connected via a single N—H···O hydrogen bond (Fig. 5). In the packing, R23(9) patterns are formed consisting of two N—H···O hydrogen bonds and a weak C—H···O hydrogen bond yielding chains running along the b axis incorporating the DMSO molecules into the chains (Fig. 6 and Table 5).
The DMAC solvate of 5-carboxyuracil, (IV), crystallizes in the monoclinic space group P21/n. The asymmetric unit consists of one 5CU molecule (A) and one disordered DMAC molecule (X), and the two molecules are connected by an N—H···O hydrogen bond enclosing a dihedral angle of 54.34 (6)° (r.m.s deviations for all non-H atoms = 0.030 Å for A and 0.041 Å for X) (Fig. 7). Again, atoms C4A and O52A show a synperiplanar arrangement [ω = 2.1 (4)°], forming the S(6) O—H···O hydrogen-bond motif. In the crystal packing, homodimers of 5CU molecules are formed via R22(8) N—H···O hydrogen bonds and the dimers show a herring-bone like arrangement whereby atom O51A is not involved in hydrogen bonds but only in weak electrostatic interactions (Fig. 8 and Table 6).
5-Carboxy-2-thiouracil–N,N-dimethylformamide (1/1), (V), crystallizes in the monoclinic space group P21/c with one 5CTU molecule (A) and one DMF molecule (X) in the asymmetric unit (Fig. 9). 5CTU molecule A exhibits an S(6) O—H···O hydrogen-bond motif [ω = 1.7 (3)°] and is linked to DMF molecule X by an N—H···O hydrogen bond enclosing a dihedral angle of 11.27 (10)° (r.m.s deviations for all non-H atoms = 0.014 Å for A and 0.014 Å for X). In the crystal packing, the 5CTU molecules form zigzag-like chains running along the b axis via R22(7) N—H···O and C—H···O hydrogen-bond motifs (Fig. 10 and Table 7).
The DMSO solvate of 5-carboxy-2-thiouracil, (VI), crystallizes in the triclinic space group P1 with one planar 5CTU molecule (A; r.m.s deviation for all non-H atoms = 0.040 Å) and one DMSO molecule (X) in the asymmetric unit (Fig. 11). Once more, an intramolecular S(6) O—H···O hydrogen-bond motif is formed [ω = 5.3 (2)°] and 5CTU molecule A is connected to DMSO molecule X via a single N—H···O hydrogen bond. In the crystal packing, molecules are connected by C21(6) interactions consisting of N—H···O hydrogen bonds, resulting in chains running along the a axis (Fig. 12 and Table 8).
The dioxane solvate of 5-carboxy-2-thiouracil, (VII), crystallizes in the triclinic space group P1. The asymmetric unit consists of one planar 5CTU molecule (A; r.m.s deviation for all non-H atoms = 0.030 Å) and three independent halves of dioxane molecules (X, Y and Z), since the solvent molecules are located at special positions (Fig. 13). Solvent molecules X and Z are connected to 5CTU molecule A via single N—H···O hydrogen bonds and an intramolecular S(6) O—H···O hydrogen-bond motif formed by A is present as well [ω = 0.2 (2)°]. Molecules A and X enclose a dihedral angle of 74.62 (7)°, and A and Z enclose a dihedral angle of 78.2 (7)° (with the mean planes of the dioxane molecules defined by the four C atoms of each molecule). In the packing, a two-dimensional network is formed via single N—H···O hydrogen bonds and R22(10) C—H···O hydrogen-bond motifs, whereby dioxane molecule Y does not form any hydrogen bonds and is located in the centre of a mesh characterized by an R1010(46) pattern (Fig. 14 and Table 9).
The ansolvate of 5-carboxy-2-thiouracil, (VIII), crystallizes in the monoclinic space group P21/c with two planar molecules A and B in the asymmetric unit (r.m.s. deviations for all non-H atoms = 0.053 Å for A and 0.046 Å for B). Molecules A and B are linked via R22(8) N—H···S hydrogen-bond motifs and are slightly tilted against each other enclosing a dihedral angle of 5.54 (19)° (Fig. 15). No intramolecular hydrogen bond is formed since the carboxy groups of adjacent 5CTU molecules form R22(8) O—H···O hydrogen-bond mofits even though atoms C4A/B and O52A/B show synperiplanar conformations, respectively [ω = 1.0 (10)° for A and -4.0 (11)° for B]. In the packing, additional R12(6) and R21(5) motifs involving N—H···O and C—H···O hydrogen bonds are formed yielding a two-dimensional network (Fig. 16 and Table 10).
Comparing the structures of (I)–(VIII), R22(8) motifs involving two N—H···O hydrogen bonds were observed in (I) and (IV), whereas in (VIII), R22(8) N—H···S hydrogen-bond motifs are formed. An intramolecular S(6) O—H···O motif was formed in six structures [i.e. (II)–(VII)], while in (VIII), the carboxy group is involved in an R22(8) O—H···O motif. In all cases, the carboxy group shows a coplanar arrangement compared to the pyrimidine ring, with atoms C4 and O52 adopting a synperiplanar conformation. This is in agreement with the CSD search which yielded the structures of the monohydrate structures of 5CU (AYEBIP; Law et al., 2004) and 5CTU (QEHSEB; Tiekink, 2001), respectively, where atoms C4 and O52 show a synperiplanar arrangement whereby intermolecular O—H···O hydrogen bonds with the water molecules are formed in both cases. However, the only cocrystal structure, i.e. 4,4'-bipyridin-1-ium uracil-5-carboxylate–4,4'-bipyridine–5-carboxyuracil (2/1/4) (HOXHIM; Nichol & Clegg, 2009), shows that the structural flexibility is great enough that atoms C4 and O52 can adopt an antiperiplanar arrangement if necessary. In all three structures, R22(8) motifs are formed consisting of either two N—H···O (AYEBIP and HOXHIM) or two N—H···S hydrogen bonds (QEHSEB). A more generalized CSD search for six-membered cyclic molecules containing a carboxy group in the β-position of a carbonyl group (Fig. 17a) (restricted to organic and not polymeric structures with determined three-dimensional coordinates and without errors) confirmed that a coplanar arrangement of the carboxy group is strongly preferred not only in structures of molecules with the uracil substructure (Fig. 17b). All 94 structures show a synperiplanar conformation illustrated by the torsion angle ω and the values of ω observed in the structures of (II)–(VIII) lie well within the same range. Even in structures where no S(6) interaction is possible due to the lack of a hydrogen-bond donor, like in GIMREA (an ansolvate of 5-formyluracil; Portalone & Colapietro, 2007) or DOTGID (cytosinium uracil-5-carboxylate monohydrate; Portalone & Colapietro, 2009), a coplanar arrangement of the residue at atom C5 with respect to the pyrimidine ring is favoured, once more illustrating the preference for coplanarity.
A substructure search of the CSD for the respective isomeric compounds 6-(hydroxymethyl)uracil (6HMU), 6-carboxyuracil (6CU) and 6-carboxy-2-thiouracil (6CTU), restricted to organic and not polymeric structures, yielded three hits for 6HMU, namely 6-(hydroxymethyl)uracil–water (1/1) (CSD refcode HIMMUM; Spek & Kooljman, 2007), 6-(hydroxymethyl)uracil–melamine–water (2/1/3) (REVVAQ; Kooijman et al., 2007) and 6-(hydroxymethyl)uracil–2,4-diamino-6-hydroxymethyl-1,3,5-triazine (1/1) (TUHJAH; Beijer et al., 1996), eight hits for 6CU, viz. 6-carboxyuracil–water (1/1) [OROTAC (Takusagawa & Shimada, 1973) and OROTAC01 (Portalone, 2008)], 6-carboxyuracil–melamine–water (1/1/1) (LIDCAE, LIDCAE01 and LIDCAE02; Xu et al., 2011), 6-carboxyuracil–dimethyl sulfoxide (1/1), dimethylammonium uracil-6-carboxylate–6-carboxyuracil (1/1) and dimethylammonium uracil-6-carboxylate–6-carboxyuracil (3/1) (XARBEZ, XARBID and XARBOJ; Gerhardt et al., 2012), and one hit for 6CTU, viz. 6-carboxy-2-thiouracil–dimethyl sulfoxide (1/1) (FOFLET; Papazoglou et al., 2014). In all these structures, R22(8) hydrogen-bond motifs consisting of two N—H···O hydrogen bonds are observed. In the cocrystal structures REVVAQ and TUHJAH, triply hydrogen-bonded ADA/DAD synthons are formed with the coformers melamine and 2,4-diamino-6-hydroxymethyl-1,3,5-triazine, respectively. Except for HIMMUM, where the O atom of the hydroxy group adopts a synclinal arrangement with respect to atom N1 of the pyrimidine ring, a coplanar arrangement compared to the pyrimidine ring is preferred in all structures.
In conclusion, even though 5-(hydroxymethyl)uracil, 5-carboxyuracil and 5-carboxy-2-thiouracil tend to form intramolecular S(6) O—H···O hydrogen-bond motifs, the structural flexibility is great enough for the formation of intermolecular hydrogen bonds instead if a suitable coformer is present. Synthons involving R22(8) interactions are favourable for the formation of doubly hydrogen-bonded complexes, but triply hydrogen-bonded ADA/DAD synthons can be taken into account for the formation of cocrystals of these compounds as well. This knowledge is helpful in order to select suitable coformers for the design of cocrystals of the title compounds and, therefore, for the development of new solid materials.
One of the main targets of crystal engineering is to establish reliable intermolecular interaction motifs, so-called synthons, which are suitable for the design of new crystal structures of molecular compounds (Desiraju, 2007). Especially hydrogen bonds are one of the most used intermolecular interactions in crystal engineering due to their strength and directionality (Aakeröy, 1997). Among the hydrogen-bonded synthons, the R22(8) motif is of particular importance (Bernstein et al., 1995) as it is formed by a large number of functional groups, for example, by carboxy or amide groups (Blagden et al., 2007; Rodríguez-Cuamatzi et al., 2007). The three compounds 5-(hydroxymethyl)uracil (5HMU), 5-carboxyuracil (5CU) and 5-carboxy-2-thiouracil (5CTU) show various biologically important properties: 5HMU is one of the major oxidative modifications of thymine and might be used as a biomarker in order to estimate biologically effective levels of carcinogen exposure (Bianchini et al., 1998); 5CU exhibits antitumour, anti-HIV and antiepileptic activity (Ross et al., 1960; Lea et al., 1992; Nichol & Clegg, 2009); and 5CTU, as well as its derivatives, exhibits anticancer and antibacterial properties (Hueso-Urena & Moreno-Carretero, 1995). All three compounds are well suited for the formation of hydrogen-bonded networks within crystal and cocrystal structures since they all contain an ADA (A = acceptor and D = donor) and an AD site. In addition, they are capable of forming an intramolecular S(6) motif involving an O—H···O hydrogen bond between the OH group of the hydroxymethyl group (5HMU) or the carboxy group (5CU and 5CTU) and the carbonyl group at atom C4. The formation of this intramolecular hydrogen bond is possible only if atom C4 and the O atom of the hydroxy group adopt a synperiplanar arrangement (defined via the torsion angle ω). In the case of 5CU and 5CTU, this is important for the formation of R22(8) carboxy-carboxy dimers since the intramolecular hydrogen bonds would prevent the formation of intermolecular hydrogen bonds. A search of the Cambridge Structural Database (CSD, Version 5.37, November 2015; Groom & Allen, 2014) restricted to organic and not polymeric structures yielded no match for 5HMU, two hits for 5CU, namely 5-carboxyuracil monohydrate (CSD refcode AYEBIP; Law et al., 2004) and 4,4'-bipyridin-1-ium uracil-5-carboxylate–4,4'-bipyridine–5-carboxyuracil (2/1/4) (HOXHIM; Nichol & Clegg, 2009), and one hit for 5CTU, viz. 5-carboxy-2-thiouracil monohydrate (QEHSEB; Tiekink, 2001). In order to gain more information about the preferred hydrogen-bonding patterns of 5HMU, 5CU and 5CTU and to point out the preferred conformation of the residue bonded to atom C5 we performed crystallization experiments from different solvents yielding two solvent free structures, (I) and (VIII), as well as the six new solvates (II)–(VII).
5-(Hydroxymethyl)uracil, (I), crystallizes in the triclinic space group P1 with one planar molecule in the asymmetric unit (r.m.s deviation for all non-H atoms = 0.040 Å), whereby atoms C4A and O51A exhibit an antiperiplanar conformation [ω = 175.0 (2)°] (Fig. 1). In the packing, chains of 5HMU molecules are formed via R22(8) N—H···O hydrogen-bond motifs, which are extended to a two-dimensional network via R24(16) and R44(20) patterns involving further O—H···O hydrogen bonds (Fig. 2 and Table 3).
The DMF solvate of 5-carboxyuracil, (II), crystallizes in the monoclinic space group P21/c. The asymmetric unit consists of one planar 5CU molecule (A) and one DMF molecule (X) connected by an N—H···O hydrogen bond and enclosing a dihedral angle of 7.75 (14)° (r.m.s deviations for all non-H atoms = 0.047 Å for A and 0.009 Å for X). Atoms C4A and O52A adopt a synperiplanar conformation [ω = -3.0 (5)°] and an S(6) motif is formed via an O—H···O hydrogen bond (Fig. 3). In the packing, additional R22(9) patterns consisting of one N—H···O and one C—H···O hydrogen bond are formed between the 5CU molecules yielding chains running along the b axis whereby the DMF molecules are located at both sides of the chains (Fig. 4 and Table 4).
The DMSO solvate of 5-carboxyuracil, (III), crystallizes in the monoclinic space group P21/c with one planar 5CU molecule (A; r.m.s. deviation for all non-H atoms = 0.010 Å) and one DMSO molecule (X) in the asymmetric unit. Atoms C4A and O52A show a synperiplanar arrangement [ω = 0.4 (4)°] leading to the S(6) O—H···O motif and molecules A and X are connected via a single N—H···O hydrogen bond (Fig. 5). In the packing, R23(9) patterns are formed consisting of two N—H···O hydrogen bonds and a weak C—H···O hydrogen bond yielding chains running along the b axis incorporating the DMSO molecules into the chains (Fig. 6 and Table 5).
The DMAC solvate of 5-carboxyuracil, (IV), crystallizes in the monoclinic space group P21/n. The asymmetric unit consists of one 5CU molecule (A) and one disordered DMAC molecule (X), and the two molecules are connected by an N—H···O hydrogen bond enclosing a dihedral angle of 54.34 (6)° (r.m.s deviations for all non-H atoms = 0.030 Å for A and 0.041 Å for X) (Fig. 7). Again, atoms C4A and O52A show a synperiplanar arrangement [ω = 2.1 (4)°], forming the S(6) O—H···O hydrogen-bond motif. In the crystal packing, homodimers of 5CU molecules are formed via R22(8) N—H···O hydrogen bonds and the dimers show a herring-bone like arrangement whereby atom O51A is not involved in hydrogen bonds but only in weak electrostatic interactions (Fig. 8 and Table 6).
5-Carboxy-2-thiouracil–N,N-dimethylformamide (1/1), (V), crystallizes in the monoclinic space group P21/c with one 5CTU molecule (A) and one DMF molecule (X) in the asymmetric unit (Fig. 9). 5CTU molecule A exhibits an S(6) O—H···O hydrogen-bond motif [ω = 1.7 (3)°] and is linked to DMF molecule X by an N—H···O hydrogen bond enclosing a dihedral angle of 11.27 (10)° (r.m.s deviations for all non-H atoms = 0.014 Å for A and 0.014 Å for X). In the crystal packing, the 5CTU molecules form zigzag-like chains running along the b axis via R22(7) N—H···O and C—H···O hydrogen-bond motifs (Fig. 10 and Table 7).
The DMSO solvate of 5-carboxy-2-thiouracil, (VI), crystallizes in the triclinic space group P1 with one planar 5CTU molecule (A; r.m.s deviation for all non-H atoms = 0.040 Å) and one DMSO molecule (X) in the asymmetric unit (Fig. 11). Once more, an intramolecular S(6) O—H···O hydrogen-bond motif is formed [ω = 5.3 (2)°] and 5CTU molecule A is connected to DMSO molecule X via a single N—H···O hydrogen bond. In the crystal packing, molecules are connected by C21(6) interactions consisting of N—H···O hydrogen bonds, resulting in chains running along the a axis (Fig. 12 and Table 8).
The dioxane solvate of 5-carboxy-2-thiouracil, (VII), crystallizes in the triclinic space group P1. The asymmetric unit consists of one planar 5CTU molecule (A; r.m.s deviation for all non-H atoms = 0.030 Å) and three independent halves of dioxane molecules (X, Y and Z), since the solvent molecules are located at special positions (Fig. 13). Solvent molecules X and Z are connected to 5CTU molecule A via single N—H···O hydrogen bonds and an intramolecular S(6) O—H···O hydrogen-bond motif formed by A is present as well [ω = 0.2 (2)°]. Molecules A and X enclose a dihedral angle of 74.62 (7)°, and A and Z enclose a dihedral angle of 78.2 (7)° (with the mean planes of the dioxane molecules defined by the four C atoms of each molecule). In the packing, a two-dimensional network is formed via single N—H···O hydrogen bonds and R22(10) C—H···O hydrogen-bond motifs, whereby dioxane molecule Y does not form any hydrogen bonds and is located in the centre of a mesh characterized by an R1010(46) pattern (Fig. 14 and Table 9).
The ansolvate of 5-carboxy-2-thiouracil, (VIII), crystallizes in the monoclinic space group P21/c with two planar molecules A and B in the asymmetric unit (r.m.s. deviations for all non-H atoms = 0.053 Å for A and 0.046 Å for B). Molecules A and B are linked via R22(8) N—H···S hydrogen-bond motifs and are slightly tilted against each other enclosing a dihedral angle of 5.54 (19)° (Fig. 15). No intramolecular hydrogen bond is formed since the carboxy groups of adjacent 5CTU molecules form R22(8) O—H···O hydrogen-bond mofits even though atoms C4A/B and O52A/B show synperiplanar conformations, respectively [ω = 1.0 (10)° for A and -4.0 (11)° for B]. In the packing, additional R12(6) and R21(5) motifs involving N—H···O and C—H···O hydrogen bonds are formed yielding a two-dimensional network (Fig. 16 and Table 10).
Comparing the structures of (I)–(VIII), R22(8) motifs involving two N—H···O hydrogen bonds were observed in (I) and (IV), whereas in (VIII), R22(8) N—H···S hydrogen-bond motifs are formed. An intramolecular S(6) O—H···O motif was formed in six structures [i.e. (II)–(VII)], while in (VIII), the carboxy group is involved in an R22(8) O—H···O motif. In all cases, the carboxy group shows a coplanar arrangement compared to the pyrimidine ring, with atoms C4 and O52 adopting a synperiplanar conformation. This is in agreement with the CSD search which yielded the structures of the monohydrate structures of 5CU (AYEBIP; Law et al., 2004) and 5CTU (QEHSEB; Tiekink, 2001), respectively, where atoms C4 and O52 show a synperiplanar arrangement whereby intermolecular O—H···O hydrogen bonds with the water molecules are formed in both cases. However, the only cocrystal structure, i.e. 4,4'-bipyridin-1-ium uracil-5-carboxylate–4,4'-bipyridine–5-carboxyuracil (2/1/4) (HOXHIM; Nichol & Clegg, 2009), shows that the structural flexibility is great enough that atoms C4 and O52 can adopt an antiperiplanar arrangement if necessary. In all three structures, R22(8) motifs are formed consisting of either two N—H···O (AYEBIP and HOXHIM) or two N—H···S hydrogen bonds (QEHSEB). A more generalized CSD search for six-membered cyclic molecules containing a carboxy group in the β-position of a carbonyl group (Fig. 17a) (restricted to organic and not polymeric structures with determined three-dimensional coordinates and without errors) confirmed that a coplanar arrangement of the carboxy group is strongly preferred not only in structures of molecules with the uracil substructure (Fig. 17b). All 94 structures show a synperiplanar conformation illustrated by the torsion angle ω and the values of ω observed in the structures of (II)–(VIII) lie well within the same range. Even in structures where no S(6) interaction is possible due to the lack of a hydrogen-bond donor, like in GIMREA (an ansolvate of 5-formyluracil; Portalone & Colapietro, 2007) or DOTGID (cytosinium uracil-5-carboxylate monohydrate; Portalone & Colapietro, 2009), a coplanar arrangement of the residue at atom C5 with respect to the pyrimidine ring is favoured, once more illustrating the preference for coplanarity.
A substructure search of the CSD for the respective isomeric compounds 6-(hydroxymethyl)uracil (6HMU), 6-carboxyuracil (6CU) and 6-carboxy-2-thiouracil (6CTU), restricted to organic and not polymeric structures, yielded three hits for 6HMU, namely 6-(hydroxymethyl)uracil–water (1/1) (CSD refcode HIMMUM; Spek & Kooljman, 2007), 6-(hydroxymethyl)uracil–melamine–water (2/1/3) (REVVAQ; Kooijman et al., 2007) and 6-(hydroxymethyl)uracil–2,4-diamino-6-hydroxymethyl-1,3,5-triazine (1/1) (TUHJAH; Beijer et al., 1996), eight hits for 6CU, viz. 6-carboxyuracil–water (1/1) [OROTAC (Takusagawa & Shimada, 1973) and OROTAC01 (Portalone, 2008)], 6-carboxyuracil–melamine–water (1/1/1) (LIDCAE, LIDCAE01 and LIDCAE02; Xu et al., 2011), 6-carboxyuracil–dimethyl sulfoxide (1/1), dimethylammonium uracil-6-carboxylate–6-carboxyuracil (1/1) and dimethylammonium uracil-6-carboxylate–6-carboxyuracil (3/1) (XARBEZ, XARBID and XARBOJ; Gerhardt et al., 2012), and one hit for 6CTU, viz. 6-carboxy-2-thiouracil–dimethyl sulfoxide (1/1) (FOFLET; Papazoglou et al., 2014). In all these structures, R22(8) hydrogen-bond motifs consisting of two N—H···O hydrogen bonds are observed. In the cocrystal structures REVVAQ and TUHJAH, triply hydrogen-bonded ADA/DAD synthons are formed with the coformers melamine and 2,4-diamino-6-hydroxymethyl-1,3,5-triazine, respectively. Except for HIMMUM, where the O atom of the hydroxy group adopts a synclinal arrangement with respect to atom N1 of the pyrimidine ring, a coplanar arrangement compared to the pyrimidine ring is preferred in all structures.
In conclusion, even though 5-(hydroxymethyl)uracil, 5-carboxyuracil and 5-carboxy-2-thiouracil tend to form intramolecular S(6) O—H···O hydrogen-bond motifs, the structural flexibility is great enough for the formation of intermolecular hydrogen bonds instead if a suitable coformer is present. Synthons involving R22(8) interactions are favourable for the formation of doubly hydrogen-bonded complexes, but triply hydrogen-bonded ADA/DAD synthons can be taken into account for the formation of cocrystals of these compounds as well. This knowledge is helpful in order to select suitable coformers for the design of cocrystals of the title compounds and, therefore, for the development of new solid materials.
Crystals of (I)–(VIII) were obtained by isothermal solvent evaporation experiments under different conditions from commercially available uracil derivatives and various solvents (Table 1). All solvents were applied without further purification and the crystallization experiments were performed at room temperature.
Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms, except those of the disordered solvent molecules, were located initially by difference Fourier synthesis. Carbon-bound H atoms were placed in calculated positions and refined using a riding model, with methyl C—H = 0.98 Å, secondary C—H = 0.99 Å and aromatic C—H = 0.95 Å, and with Uiso(H) = 1.5Ueq(C) for methyl or 1.2Ueq(C) for secondary and aromatic H atoms. Free rotation about the local threefold axis was allowed for all methyl groups except those of the minor-occupied sites of the disordered DMAC molecule in (IV) and the minor-occupied conformation of the rotationally disordered methyl group of the DMF molecule in (V). H atoms bonded to O atoms or N atoms were refined isotropically with the isotropic displacement parameters coupled to the equivalent isotropic displacement parameters of the parent N atoms or O atoms, with Uiso(H) = 1.2Ueq(N,O). Tentative free refinements of their positional coordinates resulted in an unsatisfactory wide range of D—H distances; bond lengths were therefore restrained to 0.88 (2) Å for N—H and to 0.84 (2) Å for O—H.
In (IV), the DMAC molecule is disordered over a pseudo-mirror plane along atoms O21X and C12X perpendicular to the molecular plane [site-occupancy factor for the major-occupied orientation = 0.644 (9)]. For the DMAC molecule, similarity restraints for the 1,2- and 1,3-distances were applied as well as the similar-ADP and the rigid-bond (Hirshfeld, 1976) restraints (SIMU and DELU in SHELXL2014; Sheldrick, 2015).
In (IV) [(V)?], the H atoms of the C11X methyl group of the DMF molecule show a rotational disorder [site-occupancy factor for the major-occupied conformation = 0.55 (3)].
For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
C5H6N2O3 | Z = 2 |
Mr = 142.12 | F(000) = 148 |
Triclinic, P1 | Dx = 1.652 Mg m−3 |
a = 4.874 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.663 (2) Å | Cell parameters from 3734 reflections |
c = 8.325 (3) Å | θ = 4.2–26.1° |
α = 66.97 (2)° | µ = 0.14 mm−1 |
β = 88.09 (2)° | T = 173 K |
γ = 87.07 (2)° | Block, colourless |
V = 285.7 (2) Å3 | 0.30 × 0.30 × 0.10 mm |
Stoe IPDS II two-circle diffractometer | 807 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.046 |
ω scans | θmax = 25.8°, θmin = 4.2° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −5→5 |
Tmin = 0.221, Tmax = 1.000 | k = −9→8 |
2369 measured reflections | l = −10→10 |
1091 independent reflections |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.055 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0885P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1091 reflections | Δρmax = 0.42 e Å−3 |
100 parameters | Δρmin = −0.30 e Å−3 |
C5H6N2O3 | γ = 87.07 (2)° |
Mr = 142.12 | V = 285.7 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 4.874 (3) Å | Mo Kα radiation |
b = 7.663 (2) Å | µ = 0.14 mm−1 |
c = 8.325 (3) Å | T = 173 K |
α = 66.97 (2)° | 0.30 × 0.30 × 0.10 mm |
β = 88.09 (2)° |
Stoe IPDS II two-circle diffractometer | 1091 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 807 reflections with I > 2σ(I) |
Tmin = 0.221, Tmax = 1.000 | Rint = 0.046 |
2369 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 3 restraints |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.42 e Å−3 |
1091 reflections | Δρmin = −0.30 e Å−3 |
100 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.5660 (4) | 0.7411 (3) | 0.1098 (2) | 0.0359 (5) | |
H1A | 0.642 (6) | 0.839 (3) | 0.031 (3) | 0.043* | |
C2A | 0.3415 (5) | 0.7754 (3) | 0.1960 (3) | 0.0326 (5) | |
O21A | 0.2416 (4) | 0.9366 (2) | 0.1639 (2) | 0.0412 (5) | |
N3A | 0.2324 (4) | 0.6186 (3) | 0.3222 (2) | 0.0341 (5) | |
H3A | 0.085 (5) | 0.638 (4) | 0.382 (3) | 0.041* | |
C4A | 0.3311 (5) | 0.4326 (3) | 0.3714 (3) | 0.0325 (6) | |
O41A | 0.2218 (3) | 0.3042 (2) | 0.49405 (19) | 0.0359 (5) | |
C5A | 0.5660 (5) | 0.4053 (3) | 0.2708 (3) | 0.0336 (6) | |
C51A | 0.6791 (5) | 0.2072 (3) | 0.3083 (3) | 0.0373 (6) | |
H51A | 0.7541 | 0.1505 | 0.4277 | 0.045* | |
H51B | 0.5316 | 0.1269 | 0.3004 | 0.045* | |
O51A | 0.8878 (4) | 0.2167 (3) | 0.1852 (2) | 0.0494 (6) | |
H51C | 0.956 (7) | 0.107 (5) | 0.205 (4) | 0.059* | |
C6A | 0.6701 (5) | 0.5607 (3) | 0.1439 (3) | 0.0339 (5) | |
H6A | 0.8216 | 0.5441 | 0.0757 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0353 (12) | 0.0288 (10) | 0.0358 (11) | −0.0018 (8) | 0.0057 (8) | −0.0047 (8) |
C2A | 0.0310 (13) | 0.0299 (11) | 0.0320 (11) | 0.0005 (9) | −0.0001 (9) | −0.0069 (9) |
O21A | 0.0412 (10) | 0.0290 (8) | 0.0438 (10) | 0.0023 (7) | 0.0097 (7) | −0.0051 (7) |
N3A | 0.0295 (11) | 0.0305 (10) | 0.0372 (11) | −0.0013 (8) | 0.0039 (8) | −0.0080 (8) |
C4A | 0.0302 (13) | 0.0315 (11) | 0.0332 (12) | −0.0023 (9) | −0.0018 (9) | −0.0096 (9) |
O41A | 0.0331 (10) | 0.0309 (9) | 0.0365 (9) | −0.0029 (7) | 0.0058 (7) | −0.0056 (7) |
C5A | 0.0289 (13) | 0.0332 (12) | 0.0362 (12) | −0.0016 (9) | −0.0003 (9) | −0.0109 (10) |
C51A | 0.0366 (13) | 0.0310 (11) | 0.0398 (13) | −0.0008 (9) | 0.0065 (10) | −0.0097 (9) |
O51A | 0.0500 (12) | 0.0360 (9) | 0.0550 (11) | 0.0057 (8) | 0.0147 (9) | −0.0120 (8) |
C6A | 0.0314 (13) | 0.0330 (11) | 0.0345 (12) | 0.0012 (9) | 0.0002 (9) | −0.0104 (9) |
N1A—C2A | 1.359 (3) | C4A—C5A | 1.451 (3) |
N1A—C6A | 1.371 (3) | C5A—C6A | 1.354 (3) |
N1A—H1A | 0.872 (17) | C5A—C51A | 1.503 (3) |
C2A—O21A | 1.234 (3) | C51A—O51A | 1.403 (3) |
C2A—N3A | 1.368 (3) | C51A—H51A | 0.9900 |
N3A—C4A | 1.385 (3) | C51A—H51B | 0.9900 |
N3A—H3A | 0.899 (17) | O51A—H51C | 0.84 (4) |
C4A—O41A | 1.235 (3) | C6A—H6A | 0.9500 |
C2A—N1A—C6A | 122.0 (2) | C6A—C5A—C51A | 122.9 (2) |
C2A—N1A—H1A | 117.0 (19) | C4A—C5A—C51A | 119.12 (19) |
C6A—N1A—H1A | 121.0 (19) | O51A—C51A—C5A | 108.29 (19) |
O21A—C2A—N1A | 122.8 (2) | O51A—C51A—H51A | 110.0 |
O21A—C2A—N3A | 121.8 (2) | C5A—C51A—H51A | 110.0 |
N1A—C2A—N3A | 115.5 (2) | O51A—C51A—H51B | 110.0 |
C2A—N3A—C4A | 126.5 (2) | C5A—C51A—H51B | 110.0 |
C2A—N3A—H3A | 117.2 (18) | H51A—C51A—H51B | 108.4 |
C4A—N3A—H3A | 116.2 (18) | C51A—O51A—H51C | 110 (2) |
O41A—C4A—N3A | 120.2 (2) | C5A—C6A—N1A | 122.7 (2) |
O41A—C4A—C5A | 124.6 (2) | C5A—C6A—H6A | 118.6 |
N3A—C4A—C5A | 115.17 (19) | N1A—C6A—H6A | 118.6 |
C6A—C5A—C4A | 118.0 (2) | ||
C6A—N1A—C2A—O21A | −178.2 (2) | O41A—C4A—C5A—C51A | 3.7 (4) |
C6A—N1A—C2A—N3A | 1.9 (3) | N3A—C4A—C5A—C51A | −177.0 (2) |
O21A—C2A—N3A—C4A | −178.5 (2) | C6A—C5A—C51A—O51A | −3.7 (3) |
N1A—C2A—N3A—C4A | 1.4 (3) | C4A—C5A—C51A—O51A | 175.0 (2) |
C2A—N3A—C4A—O41A | 176.2 (2) | C4A—C5A—C6A—N1A | 1.2 (4) |
C2A—N3A—C4A—C5A | −3.1 (3) | C51A—C5A—C6A—N1A | 179.9 (2) |
O41A—C4A—C5A—C6A | −177.6 (2) | C2A—N1A—C6A—C5A | −3.3 (4) |
N3A—C4A—C5A—C6A | 1.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21Ai | 0.87 (2) | 1.94 (2) | 2.804 (3) | 171 (3) |
N3A—H3A···O41Aii | 0.90 (2) | 1.92 (2) | 2.817 (3) | 176 (3) |
O51A—H51C···O21Aiii | 0.84 (4) | 1.97 (4) | 2.741 (3) | 151 (3) |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+1, −z+1; (iii) x+1, y−1, z. |
C5H4N2O4·C3H7NO | F(000) = 480 |
Mr = 229.20 | Dx = 1.510 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.671 (3) Å | Cell parameters from 8843 reflections |
b = 12.394 (2) Å | θ = 3.6–25.7° |
c = 9.381 (2) Å | µ = 0.13 mm−1 |
β = 90.17 (2)° | T = 173 K |
V = 1008.2 (4) Å3 | Block, colourless |
Z = 4 | 0.29 × 0.21 × 0.20 mm |
Stoe IPDS II two-circle diffractometer | 1180 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.132 |
ω scans | θmax = 26.2°, θmin = 3.6° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −10→10 |
Tmin = 0.415, Tmax = 1.000 | k = −15→15 |
8325 measured reflections | l = −11→11 |
1955 independent reflections |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.165 | w = 1/[σ2(Fo2) + (0.0766P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
1955 reflections | Δρmax = 0.22 e Å−3 |
156 parameters | Δρmin = −0.24 e Å−3 |
C5H4N2O4·C3H7NO | V = 1008.2 (4) Å3 |
Mr = 229.20 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.671 (3) Å | µ = 0.13 mm−1 |
b = 12.394 (2) Å | T = 173 K |
c = 9.381 (2) Å | 0.29 × 0.21 × 0.20 mm |
β = 90.17 (2)° |
Stoe IPDS II two-circle diffractometer | 1955 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1180 reflections with I > 2σ(I) |
Tmin = 0.415, Tmax = 1.000 | Rint = 0.132 |
8325 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 3 restraints |
wR(F2) = 0.165 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.22 e Å−3 |
1955 reflections | Δρmin = −0.24 e Å−3 |
156 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.1621 (4) | 0.23274 (18) | 0.3886 (3) | 0.0414 (7) | |
H1A | 0.209 (4) | 0.282 (2) | 0.445 (3) | 0.050* | |
C2A | 0.1779 (4) | 0.1250 (2) | 0.4290 (3) | 0.0417 (8) | |
O21A | 0.2561 (3) | 0.09750 (17) | 0.5296 (2) | 0.0507 (7) | |
N3A | 0.0959 (4) | 0.05409 (18) | 0.3449 (3) | 0.0427 (7) | |
H3A | 0.105 (4) | −0.0142 (17) | 0.370 (4) | 0.051* | |
C4A | −0.0004 (4) | 0.0804 (2) | 0.2347 (3) | 0.0406 (8) | |
O41A | −0.0697 (3) | 0.00920 (15) | 0.1663 (2) | 0.0494 (7) | |
C5A | −0.0170 (4) | 0.1951 (2) | 0.2060 (3) | 0.0393 (8) | |
C51A | −0.1224 (4) | 0.2348 (2) | 0.0953 (3) | 0.0402 (8) | |
O51A | −0.1430 (3) | 0.33105 (15) | 0.0716 (2) | 0.0475 (7) | |
O52A | −0.1968 (3) | 0.16145 (16) | 0.0178 (2) | 0.0506 (7) | |
H52A | −0.170 (5) | 0.100 (2) | 0.053 (4) | 0.061* | |
C6A | 0.0684 (4) | 0.2650 (2) | 0.2849 (3) | 0.0404 (8) | |
H6A | 0.0609 | 0.3400 | 0.2651 | 0.048* | |
N1X | 0.4824 (4) | 0.40624 (19) | 0.7310 (3) | 0.0476 (8) | |
C11X | 0.5839 (5) | 0.3583 (3) | 0.8373 (4) | 0.0589 (11) | |
H1XA | 0.5391 | 0.3678 | 0.9322 | 0.088* | |
H1XB | 0.6849 | 0.3936 | 0.8338 | 0.088* | |
H1XC | 0.5960 | 0.2811 | 0.8174 | 0.088* | |
C12X | 0.4650 (5) | 0.5234 (2) | 0.7336 (4) | 0.0550 (10) | |
H2XA | 0.3934 | 0.5457 | 0.6582 | 0.083* | |
H2XB | 0.5656 | 0.5574 | 0.7180 | 0.083* | |
H2XC | 0.4244 | 0.5457 | 0.8264 | 0.083* | |
C2X | 0.4080 (5) | 0.3468 (2) | 0.6357 (3) | 0.0481 (9) | |
H2X | 0.4259 | 0.2712 | 0.6373 | 0.058* | |
O21X | 0.3172 (3) | 0.38165 (17) | 0.5450 (2) | 0.0544 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.061 (2) | 0.0222 (12) | 0.0410 (15) | −0.0030 (11) | −0.0205 (14) | −0.0013 (10) |
C2A | 0.060 (3) | 0.0296 (15) | 0.0353 (17) | 0.0020 (14) | −0.0167 (17) | 0.0002 (12) |
O21A | 0.0737 (19) | 0.0336 (11) | 0.0446 (13) | 0.0036 (10) | −0.0286 (12) | 0.0028 (9) |
N3A | 0.066 (2) | 0.0196 (11) | 0.0425 (15) | 0.0017 (11) | −0.0188 (15) | 0.0008 (10) |
C4A | 0.059 (2) | 0.0227 (13) | 0.0402 (17) | −0.0015 (13) | −0.0154 (16) | 0.0009 (12) |
O41A | 0.0753 (19) | 0.0211 (10) | 0.0517 (13) | −0.0030 (10) | −0.0273 (13) | −0.0014 (9) |
C5A | 0.058 (2) | 0.0210 (13) | 0.0387 (17) | 0.0022 (13) | −0.0115 (16) | 0.0001 (11) |
C51A | 0.060 (2) | 0.0261 (14) | 0.0341 (17) | −0.0022 (13) | −0.0163 (16) | −0.0009 (11) |
O51A | 0.0696 (18) | 0.0230 (10) | 0.0499 (13) | 0.0013 (9) | −0.0248 (12) | 0.0011 (9) |
O52A | 0.076 (2) | 0.0251 (10) | 0.0508 (13) | −0.0021 (10) | −0.0352 (13) | −0.0005 (9) |
C6A | 0.061 (2) | 0.0219 (13) | 0.0384 (17) | 0.0013 (13) | −0.0136 (16) | 0.0003 (11) |
N1X | 0.064 (2) | 0.0367 (13) | 0.0417 (15) | −0.0035 (13) | −0.0202 (14) | −0.0016 (11) |
C11X | 0.072 (3) | 0.054 (2) | 0.051 (2) | 0.0048 (18) | −0.023 (2) | 0.0009 (16) |
C12X | 0.075 (3) | 0.0338 (16) | 0.056 (2) | −0.0083 (17) | −0.024 (2) | −0.0024 (15) |
C2X | 0.066 (3) | 0.0365 (16) | 0.0419 (18) | −0.0038 (15) | −0.0133 (19) | −0.0028 (14) |
O21X | 0.077 (2) | 0.0385 (12) | 0.0474 (14) | −0.0101 (11) | −0.0266 (13) | −0.0014 (10) |
N1A—C6A | 1.327 (4) | O52A—H52A | 0.859 (19) |
N1A—C2A | 1.394 (4) | C6A—H6A | 0.9500 |
N1A—H1A | 0.902 (18) | N1X—C2X | 1.325 (4) |
C2A—O21A | 1.210 (4) | N1X—C11X | 1.455 (5) |
C2A—N3A | 1.377 (4) | N1X—C12X | 1.460 (4) |
N3A—C4A | 1.366 (4) | C11X—H1XA | 0.9800 |
N3A—H3A | 0.882 (18) | C11X—H1XB | 0.9800 |
C4A—O41A | 1.245 (4) | C11X—H1XC | 0.9800 |
C4A—C5A | 1.453 (4) | C12X—H2XA | 0.9800 |
C5A—C6A | 1.358 (4) | C12X—H2XB | 0.9800 |
C5A—C51A | 1.466 (4) | C12X—H2XC | 0.9800 |
C51A—O51A | 1.226 (3) | C2X—O21X | 1.236 (4) |
C51A—O52A | 1.330 (4) | C2X—H2X | 0.9500 |
C6A—N1A—C2A | 123.2 (3) | N1A—C6A—H6A | 118.7 |
C6A—N1A—H1A | 120 (2) | C5A—C6A—H6A | 118.7 |
C2A—N1A—H1A | 117 (2) | C2X—N1X—C11X | 121.8 (3) |
O21A—C2A—N3A | 123.6 (3) | C2X—N1X—C12X | 121.0 (3) |
O21A—C2A—N1A | 122.4 (3) | C11X—N1X—C12X | 117.2 (3) |
N3A—C2A—N1A | 113.9 (3) | N1X—C11X—H1XA | 109.5 |
C4A—N3A—C2A | 126.4 (2) | N1X—C11X—H1XB | 109.5 |
C4A—N3A—H3A | 119 (3) | H1XA—C11X—H1XB | 109.5 |
C2A—N3A—H3A | 114 (3) | N1X—C11X—H1XC | 109.5 |
O41A—C4A—N3A | 120.9 (2) | H1XA—C11X—H1XC | 109.5 |
O41A—C4A—C5A | 123.4 (3) | H1XB—C11X—H1XC | 109.5 |
N3A—C4A—C5A | 115.7 (3) | N1X—C12X—H2XA | 109.5 |
C6A—C5A—C4A | 118.0 (3) | N1X—C12X—H2XB | 109.5 |
C6A—C5A—C51A | 120.7 (2) | H2XA—C12X—H2XB | 109.5 |
C4A—C5A—C51A | 121.4 (3) | N1X—C12X—H2XC | 109.5 |
O51A—C51A—O52A | 119.7 (3) | H2XA—C12X—H2XC | 109.5 |
O51A—C51A—C5A | 123.0 (3) | H2XB—C12X—H2XC | 109.5 |
O52A—C51A—C5A | 117.3 (2) | O21X—C2X—N1X | 125.3 (3) |
C51A—O52A—H52A | 105 (3) | O21X—C2X—H2X | 117.3 |
N1A—C6A—C5A | 122.6 (3) | N1X—C2X—H2X | 117.3 |
C6A—N1A—C2A—O21A | −175.2 (3) | C6A—C5A—C51A—O51A | −2.6 (5) |
C6A—N1A—C2A—N3A | 4.4 (5) | C4A—C5A—C51A—O51A | 177.5 (3) |
O21A—C2A—N3A—C4A | 176.5 (3) | C6A—C5A—C51A—O52A | 176.9 (3) |
N1A—C2A—N3A—C4A | −3.1 (5) | C4A—C5A—C51A—O52A | −3.0 (5) |
C2A—N3A—C4A—O41A | −179.5 (3) | C2A—N1A—C6A—C5A | −2.0 (5) |
C2A—N3A—C4A—C5A | −0.5 (5) | C4A—C5A—C6A—N1A | −1.9 (5) |
O41A—C4A—C5A—C6A | −177.9 (4) | C51A—C5A—C6A—N1A | 178.2 (3) |
N3A—C4A—C5A—C6A | 3.1 (5) | C11X—N1X—C2X—O21X | 178.0 (4) |
O41A—C4A—C5A—C51A | 1.9 (5) | C12X—N1X—C2X—O21X | −1.7 (6) |
N3A—C4A—C5A—C51A | −177.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21X | 0.90 (2) | 1.81 (2) | 2.712 (3) | 174 (3) |
N3A—H3A···O51Ai | 0.88 (2) | 2.02 (2) | 2.902 (3) | 176 (4) |
O52A—H52A···O41A | 0.86 (2) | 1.78 (2) | 2.590 (3) | 158 (4) |
C6A—H6A···O41Aii | 0.95 | 2.19 | 3.061 (3) | 151 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |
C5H4N2O4·C2H6OS | F(000) = 488 |
Mr = 234.23 | Dx = 1.564 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
a = 6.9341 (9) Å | Cell parameters from 5673 reflections |
b = 6.9015 (5) Å | θ = 3.5–26.0° |
c = 20.919 (3) Å | µ = 0.33 mm−1 |
β = 96.604 (10)° | T = 173 K |
V = 994.5 (2) Å3 | Block, colourless |
Z = 4 | 0.25 × 0.12 × 0.10 mm |
Stoe IPDS II two-circle diffractometer | 1443 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.074 |
ω scans | θmax = 25.8°, θmin = 3.5° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −8→7 |
Tmin = 0.565, Tmax = 1.000 | k = −8→8 |
7444 measured reflections | l = −25→25 |
1900 independent reflections |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0512P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1900 reflections | Δρmax = 0.25 e Å−3 |
147 parameters | Δρmin = −0.44 e Å−3 |
C5H4N2O4·C2H6OS | V = 994.5 (2) Å3 |
Mr = 234.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.9341 (9) Å | µ = 0.33 mm−1 |
b = 6.9015 (5) Å | T = 173 K |
c = 20.919 (3) Å | 0.25 × 0.12 × 0.10 mm |
β = 96.604 (10)° |
Stoe IPDS II two-circle diffractometer | 1900 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1443 reflections with I > 2σ(I) |
Tmin = 0.565, Tmax = 1.000 | Rint = 0.074 |
7444 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 3 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.25 e Å−3 |
1900 reflections | Δρmin = −0.44 e Å−3 |
147 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.1715 (3) | 0.7392 (3) | 0.45369 (9) | 0.0207 (5) | |
H1A | 0.136 (4) | 0.842 (3) | 0.4314 (12) | 0.025* | |
C2A | 0.1206 (4) | 0.5693 (3) | 0.42009 (11) | 0.0205 (5) | |
O21A | 0.0326 (3) | 0.5673 (2) | 0.36653 (8) | 0.0278 (4) | |
N3A | 0.1761 (3) | 0.4014 (3) | 0.45324 (9) | 0.0204 (4) | |
H3A | 0.144 (4) | 0.296 (3) | 0.4319 (12) | 0.025* | |
C4A | 0.2719 (4) | 0.3887 (3) | 0.51435 (11) | 0.0194 (5) | |
O41A | 0.3128 (3) | 0.2287 (2) | 0.53880 (8) | 0.0255 (4) | |
C5A | 0.3178 (4) | 0.5735 (3) | 0.54612 (11) | 0.0195 (5) | |
C51A | 0.4193 (4) | 0.5817 (4) | 0.61195 (11) | 0.0231 (5) | |
O51A | 0.4618 (3) | 0.7319 (3) | 0.64053 (9) | 0.0318 (5) | |
O52A | 0.4664 (3) | 0.4103 (3) | 0.63979 (8) | 0.0300 (4) | |
H52A | 0.426 (5) | 0.329 (4) | 0.6109 (12) | 0.036* | |
C6A | 0.2653 (4) | 0.7402 (3) | 0.51367 (11) | 0.0199 (5) | |
H6A | 0.2960 | 0.8610 | 0.5341 | 0.024* | |
S1X | 0.03084 (10) | 1.09275 (8) | 0.31404 (3) | 0.0236 (2) | |
O11X | 0.0627 (3) | 1.0730 (2) | 0.38765 (8) | 0.0265 (4) | |
C11X | 0.2118 (4) | 0.9439 (4) | 0.28519 (13) | 0.0278 (6) | |
H1XA | 0.3405 | 0.9977 | 0.2993 | 0.042* | |
H1XB | 0.1916 | 0.9397 | 0.2381 | 0.042* | |
H1XC | 0.2030 | 0.8125 | 0.3024 | 0.042* | |
C12X | −0.1787 (4) | 0.9502 (4) | 0.28980 (13) | 0.0273 (6) | |
H2XA | −0.1603 | 0.8195 | 0.3078 | 0.041* | |
H2XB | −0.1988 | 0.9425 | 0.2427 | 0.041* | |
H2XC | −0.2924 | 1.0101 | 0.3055 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0263 (13) | 0.0144 (9) | 0.0215 (11) | 0.0028 (9) | 0.0028 (9) | 0.0025 (8) |
C2A | 0.0205 (14) | 0.0181 (11) | 0.0238 (13) | 0.0002 (10) | 0.0059 (10) | 0.0005 (9) |
O21A | 0.0383 (12) | 0.0231 (9) | 0.0207 (9) | 0.0013 (8) | −0.0023 (8) | 0.0020 (7) |
N3A | 0.0246 (12) | 0.0156 (9) | 0.0211 (10) | 0.0005 (9) | 0.0024 (8) | −0.0027 (8) |
C4A | 0.0178 (13) | 0.0172 (10) | 0.0240 (12) | 0.0010 (10) | 0.0063 (10) | −0.0015 (10) |
O41A | 0.0326 (11) | 0.0162 (8) | 0.0277 (9) | 0.0040 (8) | 0.0033 (8) | 0.0047 (7) |
C5A | 0.0184 (13) | 0.0201 (11) | 0.0206 (12) | 0.0006 (11) | 0.0055 (9) | −0.0004 (9) |
C51A | 0.0236 (14) | 0.0250 (12) | 0.0216 (12) | 0.0010 (11) | 0.0057 (10) | −0.0016 (10) |
O51A | 0.0397 (13) | 0.0283 (9) | 0.0260 (10) | 0.0002 (9) | −0.0027 (8) | −0.0075 (8) |
O52A | 0.0369 (12) | 0.0277 (9) | 0.0240 (9) | 0.0042 (9) | −0.0023 (8) | 0.0010 (8) |
C6A | 0.0217 (15) | 0.0163 (10) | 0.0229 (12) | −0.0029 (10) | 0.0074 (10) | −0.0032 (9) |
S1X | 0.0338 (4) | 0.0162 (3) | 0.0205 (3) | 0.0001 (3) | 0.0014 (2) | 0.0007 (2) |
O11X | 0.0438 (12) | 0.0149 (8) | 0.0202 (9) | −0.0007 (8) | 0.0011 (8) | −0.0011 (7) |
C11X | 0.0300 (16) | 0.0268 (13) | 0.0270 (13) | −0.0003 (12) | 0.0045 (11) | −0.0008 (10) |
C12X | 0.0252 (15) | 0.0281 (13) | 0.0285 (14) | 0.0000 (11) | 0.0019 (11) | −0.0016 (10) |
N1A—C6A | 1.345 (3) | C51A—O52A | 1.343 (3) |
N1A—C2A | 1.392 (3) | O52A—H52A | 0.847 (18) |
N1A—H1A | 0.867 (17) | C6A—H6A | 0.9500 |
C2A—O21A | 1.213 (3) | S1X—O11X | 1.5364 (17) |
C2A—N3A | 1.382 (3) | S1X—C12X | 1.779 (3) |
N3A—C4A | 1.374 (3) | S1X—C11X | 1.780 (3) |
N3A—H3A | 0.867 (17) | C11X—H1XA | 0.9800 |
C4A—O41A | 1.236 (3) | C11X—H1XB | 0.9800 |
C4A—C5A | 1.457 (3) | C11X—H1XC | 0.9800 |
C5A—C6A | 1.364 (3) | C12X—H2XA | 0.9800 |
C5A—C51A | 1.474 (3) | C12X—H2XB | 0.9800 |
C51A—O51A | 1.216 (3) | C12X—H2XC | 0.9800 |
C6A—N1A—C2A | 122.9 (2) | N1A—C6A—C5A | 122.2 (2) |
C6A—N1A—H1A | 125.1 (18) | N1A—C6A—H6A | 118.9 |
C2A—N1A—H1A | 112.1 (18) | C5A—C6A—H6A | 118.9 |
O21A—C2A—N3A | 122.4 (2) | O11X—S1X—C12X | 104.76 (12) |
O21A—C2A—N1A | 123.2 (2) | O11X—S1X—C11X | 105.25 (12) |
N3A—C2A—N1A | 114.4 (2) | C12X—S1X—C11X | 99.72 (13) |
C4A—N3A—C2A | 126.7 (2) | S1X—C11X—H1XA | 109.5 |
C4A—N3A—H3A | 119.6 (18) | S1X—C11X—H1XB | 109.5 |
C2A—N3A—H3A | 113.7 (18) | H1XA—C11X—H1XB | 109.5 |
O41A—C4A—N3A | 120.4 (2) | S1X—C11X—H1XC | 109.5 |
O41A—C4A—C5A | 124.5 (2) | H1XA—C11X—H1XC | 109.5 |
N3A—C4A—C5A | 115.2 (2) | H1XB—C11X—H1XC | 109.5 |
C6A—C5A—C4A | 118.7 (2) | S1X—C12X—H2XA | 109.5 |
C6A—C5A—C51A | 120.3 (2) | S1X—C12X—H2XB | 109.5 |
C4A—C5A—C51A | 121.1 (2) | H2XA—C12X—H2XB | 109.5 |
O51A—C51A—O52A | 120.3 (2) | S1X—C12X—H2XC | 109.5 |
O51A—C51A—C5A | 123.7 (2) | H2XA—C12X—H2XC | 109.5 |
O52A—C51A—C5A | 115.9 (2) | H2XB—C12X—H2XC | 109.5 |
C51A—O52A—H52A | 103 (2) | ||
C6A—N1A—C2A—O21A | 178.5 (2) | N3A—C4A—C5A—C51A | 179.6 (2) |
C6A—N1A—C2A—N3A | −0.6 (4) | C6A—C5A—C51A—O51A | −0.2 (4) |
O21A—C2A—N3A—C4A | −178.5 (2) | C4A—C5A—C51A—O51A | 179.6 (2) |
N1A—C2A—N3A—C4A | 0.6 (4) | C6A—C5A—C51A—O52A | −179.5 (2) |
C2A—N3A—C4A—O41A | 179.7 (2) | C4A—C5A—C51A—O52A | 0.4 (4) |
C2A—N3A—C4A—C5A | −0.1 (4) | C2A—N1A—C6A—C5A | 0.1 (4) |
O41A—C4A—C5A—C6A | 179.7 (2) | C4A—C5A—C6A—N1A | 0.5 (4) |
N3A—C4A—C5A—C6A | −0.5 (4) | C51A—C5A—C6A—N1A | −179.6 (2) |
O41A—C4A—C5A—C51A | −0.1 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O52A—H52A···O41A | 0.85 (2) | 1.76 (2) | 2.579 (3) | 162 (3) |
N1A—H1A···O11X | 0.87 (2) | 1.88 (2) | 2.747 (3) | 176 (3) |
N3A—H3A···O11Xi | 0.87 (2) | 1.85 (2) | 2.718 (3) | 177 (3) |
C6A—H6A···O41Aii | 0.95 | 2.54 | 3.422 (3) | 154 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
C5H4N2O4·C4H9NO | F(000) = 512 |
Mr = 243.22 | Dx = 1.472 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.7707 (19) Å | Cell parameters from 7500 reflections |
b = 6.1053 (10) Å | θ = 3.6–26.0° |
c = 15.271 (3) Å | µ = 0.12 mm−1 |
β = 90.858 (13)° | T = 173 K |
V = 1097.3 (3) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.25 × 0.15 mm |
Stoe IPDS II two-circle diffractometer | 1328 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.065 |
ω scans | θmax = 25.9°, θmin = 3.6° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −14→12 |
Tmin = 0.317, Tmax = 1.000 | k = −7→7 |
8148 measured reflections | l = −18→18 |
2119 independent reflections |
Refinement on F2 | 131 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0743P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
2119 reflections | Δρmax = 0.17 e Å−3 |
185 parameters | Δρmin = −0.25 e Å−3 |
C5H4N2O4·C4H9NO | V = 1097.3 (3) Å3 |
Mr = 243.22 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.7707 (19) Å | µ = 0.12 mm−1 |
b = 6.1053 (10) Å | T = 173 K |
c = 15.271 (3) Å | 0.30 × 0.25 × 0.15 mm |
β = 90.858 (13)° |
Stoe IPDS II two-circle diffractometer | 2119 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1328 reflections with I > 2σ(I) |
Tmin = 0.317, Tmax = 1.000 | Rint = 0.065 |
8148 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 131 restraints |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.17 e Å−3 |
2119 reflections | Δρmin = −0.25 e Å−3 |
185 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.2926 (2) | 0.3079 (4) | 0.59331 (16) | 0.0472 (6) | |
H1A | 0.2214 (17) | 0.266 (5) | 0.583 (2) | 0.057* | |
C2A | 0.3761 (3) | 0.1841 (4) | 0.55581 (17) | 0.0454 (7) | |
O21A | 0.35541 (17) | 0.0140 (3) | 0.51590 (13) | 0.0514 (5) | |
N3A | 0.4839 (2) | 0.2636 (4) | 0.56715 (15) | 0.0462 (6) | |
H3A | 0.538 (2) | 0.184 (4) | 0.5453 (19) | 0.055* | |
C4A | 0.5141 (3) | 0.4552 (4) | 0.60850 (17) | 0.0458 (7) | |
O41A | 0.61524 (18) | 0.5132 (3) | 0.61118 (14) | 0.0550 (5) | |
C5A | 0.4216 (3) | 0.5770 (4) | 0.64618 (17) | 0.0459 (7) | |
C51A | 0.4404 (3) | 0.7878 (5) | 0.69157 (18) | 0.0511 (7) | |
O51A | 0.3652 (2) | 0.8934 (3) | 0.72479 (14) | 0.0621 (6) | |
O52A | 0.5472 (2) | 0.8624 (3) | 0.69315 (14) | 0.0586 (6) | |
H52A | 0.587 (3) | 0.762 (5) | 0.666 (2) | 0.070* | |
C6A | 0.3158 (3) | 0.4958 (4) | 0.63678 (18) | 0.0473 (7) | |
H6A | 0.2546 | 0.5742 | 0.6619 | 0.057* | |
C11X | 0.0690 (4) | −0.1555 (6) | 0.6380 (3) | 0.0880 (13) | |
H1XA | 0.1329 | −0.0691 | 0.6164 | 0.132* | 0.644 (9) |
H1XB | 0.0573 | −0.2835 | 0.6001 | 0.132* | 0.644 (9) |
H1XC | 0.0857 | −0.2043 | 0.6979 | 0.132* | 0.644 (9) |
H1A' | 0.0070 | −0.2372 | 0.6650 | 0.132* | 0.356 (9) |
H1B' | 0.0980 | −0.2386 | 0.5881 | 0.132* | 0.356 (9) |
H1C' | 0.1303 | −0.1332 | 0.6812 | 0.132* | 0.356 (9) |
C12X | −0.1503 (3) | −0.0981 (6) | 0.6608 (2) | 0.0716 (10) | |
H1XD | −0.1408 | −0.2267 | 0.6986 | 0.107* | 0.644 (9) |
H1XE | −0.1927 | −0.1395 | 0.6076 | 0.107* | 0.644 (9) |
H1XF | −0.1922 | 0.0155 | 0.6921 | 0.107* | 0.644 (9) |
H1D' | −0.2303 | −0.0573 | 0.6674 | 0.107* | 0.356 (9) |
H1E' | −0.1451 | −0.2268 | 0.6227 | 0.107* | 0.356 (9) |
H1F' | −0.1171 | −0.1324 | 0.7184 | 0.107* | 0.356 (9) |
O21X | 0.07125 (19) | 0.2298 (4) | 0.56743 (14) | 0.0619 (6) | |
C3X | −0.1352 (3) | 0.3063 (6) | 0.5873 (3) | 0.0751 (10) | |
H1XG | −0.1931 | 0.2233 | 0.5546 | 0.113* | 0.644 (9) |
H1XH | −0.1201 | 0.4444 | 0.5570 | 0.113* | 0.644 (9) |
H1XI | −0.1626 | 0.3372 | 0.6463 | 0.113* | 0.644 (9) |
H1G' | −0.2166 | 0.3143 | 0.5995 | 0.113* | 0.356 (9) |
H1H' | −0.0957 | 0.4275 | 0.6168 | 0.113* | 0.356 (9) |
H1I' | −0.1238 | 0.3166 | 0.5240 | 0.113* | 0.356 (9) |
N1X | −0.0390 (5) | −0.0142 (8) | 0.6371 (3) | 0.0602 (14) | 0.644 (9) |
C2X | −0.0258 (5) | 0.1718 (9) | 0.5936 (3) | 0.0553 (15) | 0.644 (9) |
N1X' | −0.0874 (7) | 0.0871 (14) | 0.6212 (5) | 0.054 (2) | 0.356 (9) |
C2X' | 0.0248 (8) | 0.0672 (15) | 0.6061 (6) | 0.048 (2) | 0.356 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0469 (15) | 0.0409 (12) | 0.0537 (14) | 0.0021 (11) | 0.0015 (11) | −0.0008 (10) |
C2A | 0.0514 (18) | 0.0418 (14) | 0.0428 (15) | 0.0031 (13) | −0.0012 (12) | 0.0029 (12) |
O21A | 0.0551 (13) | 0.0425 (10) | 0.0565 (12) | −0.0003 (9) | 0.0002 (9) | −0.0068 (9) |
N3A | 0.0486 (15) | 0.0398 (12) | 0.0501 (13) | 0.0049 (11) | 0.0016 (11) | −0.0016 (10) |
C4A | 0.0541 (19) | 0.0382 (14) | 0.0452 (15) | 0.0030 (13) | −0.0004 (13) | 0.0046 (11) |
O41A | 0.0528 (13) | 0.0465 (11) | 0.0658 (13) | −0.0006 (10) | 0.0005 (10) | −0.0031 (9) |
C5A | 0.0563 (18) | 0.0399 (14) | 0.0414 (14) | 0.0024 (13) | 0.0015 (13) | 0.0031 (11) |
C51A | 0.065 (2) | 0.0448 (15) | 0.0434 (16) | −0.0022 (15) | 0.0010 (14) | 0.0014 (12) |
O51A | 0.0735 (16) | 0.0527 (12) | 0.0605 (13) | 0.0043 (11) | 0.0085 (12) | −0.0110 (10) |
O52A | 0.0685 (16) | 0.0461 (11) | 0.0613 (13) | −0.0032 (10) | 0.0000 (11) | −0.0057 (9) |
C6A | 0.0542 (18) | 0.0417 (14) | 0.0460 (15) | 0.0056 (13) | 0.0032 (13) | 0.0035 (12) |
C11X | 0.110 (3) | 0.059 (2) | 0.094 (3) | 0.038 (2) | −0.039 (2) | −0.0210 (18) |
C12X | 0.076 (2) | 0.066 (2) | 0.073 (2) | −0.0150 (18) | 0.0054 (19) | −0.0030 (17) |
O21X | 0.0549 (14) | 0.0620 (13) | 0.0688 (14) | −0.0009 (11) | −0.0006 (11) | 0.0002 (11) |
C3X | 0.070 (2) | 0.063 (2) | 0.092 (3) | 0.0218 (17) | −0.0242 (19) | −0.0198 (18) |
N1X | 0.069 (4) | 0.051 (3) | 0.061 (3) | −0.003 (2) | −0.005 (2) | −0.005 (2) |
C2X | 0.068 (4) | 0.051 (3) | 0.046 (3) | −0.001 (3) | −0.006 (3) | −0.008 (2) |
N1X' | 0.049 (5) | 0.051 (5) | 0.063 (5) | 0.003 (3) | −0.002 (4) | −0.008 (4) |
C2X' | 0.049 (5) | 0.048 (5) | 0.047 (5) | 0.004 (4) | −0.008 (4) | −0.011 (4) |
N1A—C6A | 1.351 (4) | C11X—H1C' | 0.9800 |
N1A—C2A | 1.372 (3) | C12X—N1X | 1.458 (6) |
N1A—H1A | 0.888 (18) | C12X—N1X' | 1.485 (9) |
C2A—O21A | 1.227 (3) | C12X—H1XD | 0.9800 |
C2A—N3A | 1.367 (4) | C12X—H1XE | 0.9800 |
N3A—C4A | 1.374 (4) | C12X—H1XF | 0.9800 |
N3A—H3A | 0.873 (18) | C12X—H1D' | 0.9800 |
C4A—O41A | 1.242 (3) | C12X—H1E' | 0.9800 |
C4A—C5A | 1.445 (4) | C12X—H1F' | 0.9800 |
C5A—C6A | 1.346 (4) | O21X—C2X | 1.267 (6) |
C5A—C51A | 1.477 (4) | O21X—C2X' | 1.282 (9) |
C51A—O51A | 1.213 (4) | C3X—C2X | 1.529 (7) |
C51A—O52A | 1.337 (4) | C3X—N1X' | 1.538 (9) |
O52A—H52A | 0.873 (18) | C3X—H1XG | 0.9800 |
C6A—H6A | 0.9500 | C3X—H1XH | 0.9800 |
C11X—C2X' | 1.533 (10) | C3X—H1XI | 0.9800 |
C11X—N1X | 1.536 (7) | C3X—H1G' | 0.9800 |
C11X—H1XA | 0.9800 | C3X—H1H' | 0.9800 |
C11X—H1XB | 0.9800 | C3X—H1I' | 0.9800 |
C11X—H1XC | 0.9800 | N1X—C2X | 1.325 (8) |
C11X—H1A' | 0.9800 | N1X'—C2X' | 1.350 (12) |
C11X—H1B' | 0.9800 | ||
C6A—N1A—C2A | 122.1 (3) | N1X—C12X—H1XE | 109.5 |
C6A—N1A—H1A | 121 (2) | H1XD—C12X—H1XE | 109.5 |
C2A—N1A—H1A | 117 (2) | N1X—C12X—H1XF | 109.5 |
O21A—C2A—N3A | 122.7 (3) | H1XD—C12X—H1XF | 109.5 |
O21A—C2A—N1A | 122.3 (3) | H1XE—C12X—H1XF | 109.5 |
N3A—C2A—N1A | 114.9 (2) | N1X'—C12X—H1D' | 109.5 |
C2A—N3A—C4A | 126.4 (2) | N1X'—C12X—H1E' | 109.5 |
C2A—N3A—H3A | 116 (2) | H1D'—C12X—H1E' | 109.5 |
C4A—N3A—H3A | 118 (2) | N1X'—C12X—H1F' | 109.5 |
O41A—C4A—N3A | 119.9 (3) | H1D'—C12X—H1F' | 109.5 |
O41A—C4A—C5A | 124.6 (3) | H1E'—C12X—H1F' | 109.5 |
N3A—C4A—C5A | 115.5 (3) | C2X—C3X—H1XG | 109.5 |
C6A—C5A—C4A | 118.0 (3) | C2X—C3X—H1XH | 109.5 |
C6A—C5A—C51A | 120.2 (3) | H1XG—C3X—H1XH | 109.5 |
C4A—C5A—C51A | 121.8 (3) | C2X—C3X—H1XI | 109.5 |
O51A—C51A—O52A | 120.2 (3) | H1XG—C3X—H1XI | 109.5 |
O51A—C51A—C5A | 123.7 (3) | H1XH—C3X—H1XI | 109.5 |
O52A—C51A—C5A | 116.1 (3) | N1X'—C3X—H1G' | 109.5 |
C51A—O52A—H52A | 105 (2) | N1X'—C3X—H1H' | 109.5 |
C5A—C6A—N1A | 123.0 (3) | H1G'—C3X—H1H' | 109.5 |
C5A—C6A—H6A | 118.5 | N1X'—C3X—H1I' | 109.5 |
N1A—C6A—H6A | 118.5 | H1G'—C3X—H1I' | 109.5 |
N1X—C11X—H1XA | 109.5 | H1H'—C3X—H1I' | 109.5 |
N1X—C11X—H1XB | 109.5 | C2X—N1X—C12X | 122.5 (6) |
H1XA—C11X—H1XB | 109.5 | C2X—N1X—C11X | 112.5 (5) |
N1X—C11X—H1XC | 109.5 | C12X—N1X—C11X | 123.2 (4) |
H1XA—C11X—H1XC | 109.5 | O21X—C2X—N1X | 120.7 (6) |
H1XB—C11X—H1XC | 109.5 | O21X—C2X—C3X | 126.4 (5) |
C2X'—C11X—H1A' | 109.5 | N1X—C2X—C3X | 112.8 (5) |
C2X'—C11X—H1B' | 109.5 | C2X'—N1X'—C12X | 119.7 (8) |
H1A'—C11X—H1B' | 109.5 | C2X'—N1X'—C3X | 112.0 (8) |
C2X'—C11X—H1C' | 109.5 | C12X—N1X'—C3X | 128.1 (6) |
H1A'—C11X—H1C' | 109.5 | O21X—C2X'—N1X' | 115.7 (9) |
H1B'—C11X—H1C' | 109.5 | O21X—C2X'—C11X | 133.5 (7) |
N1X—C12X—H1XD | 109.5 | N1X'—C2X'—C11X | 110.8 (8) |
C6A—N1A—C2A—O21A | −179.6 (3) | C4A—C5A—C51A—O52A | 2.1 (4) |
C6A—N1A—C2A—N3A | 1.1 (4) | C4A—C5A—C6A—N1A | −0.6 (4) |
O21A—C2A—N3A—C4A | 177.9 (3) | C51A—C5A—C6A—N1A | 177.6 (2) |
N1A—C2A—N3A—C4A | −2.8 (4) | C2A—N1A—C6A—C5A | 0.5 (4) |
C2A—N3A—C4A—O41A | −177.0 (3) | C12X—N1X—C2X—O21X | −173.7 (4) |
C2A—N3A—C4A—C5A | 2.7 (4) | C11X—N1X—C2X—O21X | −8.6 (6) |
O41A—C4A—C5A—C6A | 178.8 (3) | C12X—N1X—C2X—C3X | 11.1 (6) |
N3A—C4A—C5A—C6A | −0.9 (4) | C11X—N1X—C2X—C3X | 176.2 (3) |
O41A—C4A—C5A—C51A | 0.6 (4) | C12X—N1X'—C2X'—O21X | 176.3 (6) |
N3A—C4A—C5A—C51A | −179.1 (2) | C3X—N1X'—C2X'—O21X | 0.2 (9) |
C6A—C5A—C51A—O51A | 2.7 (4) | C12X—N1X'—C2X'—C11X | −2.1 (9) |
C4A—C5A—C51A—O51A | −179.2 (3) | C3X—N1X'—C2X'—C11X | −178.2 (5) |
C6A—C5A—C51A—O52A | −176.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21X | 0.89 (2) | 1.79 (2) | 2.672 (3) | 170 (3) |
O52A—H52A···O41A | 0.87 (2) | 1.77 (2) | 2.605 (3) | 158 (3) |
N3A—H3A···O21Ai | 0.87 (2) | 1.98 (2) | 2.851 (3) | 172 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
C5H4N2O3S·C3H7NO | F(000) = 512 |
Mr = 245.26 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1742 (10) Å | Cell parameters from 15516 reflections |
b = 11.4616 (12) Å | θ = 3.6–26.1° |
c = 9.9715 (11) Å | µ = 0.29 mm−1 |
β = 104.318 (8)° | T = 173 K |
V = 1126.7 (2) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.30 × 0.30 mm |
Stoe IPDS II two-circle diffractometer | 1796 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.045 |
ω scans | θmax = 25.8°, θmin = 3.6° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −11→12 |
Tmin = 0.499, Tmax = 1.000 | k = −14→13 |
8433 measured reflections | l = −12→12 |
2163 independent reflections |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.049P)2 + 0.2199P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2163 reflections | Δρmax = 0.27 e Å−3 |
157 parameters | Δρmin = −0.20 e Å−3 |
C5H4N2O3S·C3H7NO | V = 1126.7 (2) Å3 |
Mr = 245.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.1742 (10) Å | µ = 0.29 mm−1 |
b = 11.4616 (12) Å | T = 173 K |
c = 9.9715 (11) Å | 0.40 × 0.30 × 0.30 mm |
β = 104.318 (8)° |
Stoe IPDS II two-circle diffractometer | 2163 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1796 reflections with I > 2σ(I) |
Tmin = 0.499, Tmax = 1.000 | Rint = 0.045 |
8433 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 3 restraints |
wR(F2) = 0.093 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.27 e Å−3 |
2163 reflections | Δρmin = −0.20 e Å−3 |
157 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.12196 (16) | 0.62099 (12) | 0.62644 (16) | 0.0278 (3) | |
H1A | 0.103 (2) | 0.5523 (15) | 0.654 (2) | 0.033* | |
C2A | 0.21236 (18) | 0.62753 (15) | 0.54497 (18) | 0.0263 (4) | |
S21A | 0.27742 (5) | 0.50942 (4) | 0.49137 (5) | 0.03359 (16) | |
N3A | 0.24350 (16) | 0.73863 (12) | 0.51204 (15) | 0.0257 (3) | |
H3A | 0.3028 (19) | 0.7464 (17) | 0.461 (2) | 0.031* | |
C4A | 0.19450 (18) | 0.83982 (14) | 0.55586 (17) | 0.0251 (4) | |
O41A | 0.23399 (14) | 0.93613 (10) | 0.52405 (14) | 0.0328 (3) | |
C5A | 0.09886 (18) | 0.82528 (14) | 0.64013 (17) | 0.0252 (4) | |
C51A | 0.03890 (18) | 0.92657 (14) | 0.69386 (19) | 0.0271 (4) | |
O51A | −0.03996 (14) | 0.91647 (10) | 0.76718 (14) | 0.0336 (3) | |
O52A | 0.07515 (14) | 1.03106 (10) | 0.65730 (14) | 0.0316 (3) | |
H52A | 0.130 (2) | 1.0176 (19) | 0.612 (2) | 0.038* | |
C6A | 0.06725 (19) | 0.71524 (14) | 0.67164 (18) | 0.0262 (4) | |
H6A | 0.0047 | 0.7046 | 0.7272 | 0.031* | |
N1X | 0.55873 (16) | 0.68861 (13) | 0.22344 (16) | 0.0296 (3) | |
C11X | 0.6186 (3) | 0.8005 (2) | 0.2065 (3) | 0.0550 (7) | |
H1XA | 0.5909 | 0.8241 | 0.1091 | 0.083* | 0.55 (3) |
H1XB | 0.7176 | 0.7944 | 0.2353 | 0.083* | 0.55 (3) |
H1XC | 0.5877 | 0.8590 | 0.2637 | 0.083* | 0.55 (3) |
H1XD | 0.6835 | 0.7911 | 0.1493 | 0.083* | 0.45 (3) |
H1XE | 0.5471 | 0.8551 | 0.1613 | 0.083* | 0.45 (3) |
H1XF | 0.6656 | 0.8313 | 0.2975 | 0.083* | 0.45 (3) |
C12X | 0.6001 (2) | 0.58867 (17) | 0.1524 (2) | 0.0372 (5) | |
H2XA | 0.5542 | 0.5182 | 0.1732 | 0.056* | |
H2XB | 0.6986 | 0.5782 | 0.1842 | 0.056* | |
H2XC | 0.5754 | 0.6026 | 0.0524 | 0.056* | |
C2X | 0.46777 (19) | 0.67999 (15) | 0.29704 (18) | 0.0284 (4) | |
H2X | 0.4322 | 0.6047 | 0.3070 | 0.034* | |
O21X | 0.42527 (15) | 0.76303 (11) | 0.35421 (14) | 0.0370 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0346 (9) | 0.0204 (7) | 0.0335 (8) | 0.0003 (6) | 0.0180 (7) | 0.0020 (6) |
C2A | 0.0293 (9) | 0.0243 (8) | 0.0264 (9) | 0.0008 (7) | 0.0089 (7) | 0.0002 (6) |
S21A | 0.0438 (3) | 0.0244 (2) | 0.0384 (3) | 0.00722 (19) | 0.0212 (2) | −0.00143 (17) |
N3A | 0.0290 (8) | 0.0240 (7) | 0.0290 (8) | 0.0007 (6) | 0.0163 (6) | 0.0011 (6) |
C4A | 0.0261 (9) | 0.0240 (8) | 0.0264 (9) | 0.0013 (7) | 0.0089 (7) | 0.0014 (6) |
O41A | 0.0378 (8) | 0.0233 (6) | 0.0433 (7) | −0.0016 (5) | 0.0217 (6) | 0.0041 (5) |
C5A | 0.0263 (9) | 0.0242 (8) | 0.0274 (9) | 0.0011 (7) | 0.0109 (7) | −0.0003 (6) |
C51A | 0.0268 (9) | 0.0230 (8) | 0.0328 (10) | 0.0024 (7) | 0.0096 (8) | −0.0013 (7) |
O51A | 0.0348 (7) | 0.0278 (6) | 0.0446 (8) | 0.0017 (5) | 0.0220 (6) | −0.0047 (5) |
O52A | 0.0388 (8) | 0.0208 (6) | 0.0400 (7) | 0.0012 (5) | 0.0187 (6) | 0.0003 (5) |
C6A | 0.0280 (9) | 0.0255 (8) | 0.0287 (9) | 0.0019 (7) | 0.0137 (7) | −0.0002 (7) |
N1X | 0.0313 (9) | 0.0272 (7) | 0.0348 (8) | −0.0001 (6) | 0.0166 (7) | −0.0001 (6) |
C11X | 0.0659 (17) | 0.0409 (11) | 0.0741 (16) | −0.0173 (11) | 0.0474 (14) | −0.0096 (11) |
C12X | 0.0443 (12) | 0.0358 (10) | 0.0360 (10) | 0.0070 (9) | 0.0181 (9) | −0.0025 (8) |
C2X | 0.0291 (9) | 0.0281 (9) | 0.0294 (9) | −0.0006 (7) | 0.0099 (8) | 0.0017 (7) |
O21X | 0.0416 (8) | 0.0349 (7) | 0.0423 (8) | 0.0016 (6) | 0.0250 (7) | −0.0018 (6) |
N1A—C6A | 1.343 (2) | N1X—C2X | 1.319 (2) |
N1A—C2A | 1.372 (2) | N1X—C11X | 1.448 (3) |
N1A—H1A | 0.872 (16) | N1X—C12X | 1.462 (2) |
C2A—N3A | 1.372 (2) | C11X—H1XA | 0.9800 |
C2A—S21A | 1.6526 (17) | C11X—H1XB | 0.9800 |
N3A—C4A | 1.376 (2) | C11X—H1XC | 0.9800 |
N3A—H3A | 0.881 (16) | C11X—H1XD | 0.9800 |
C4A—O41A | 1.242 (2) | C11X—H1XE | 0.9800 |
C4A—C5A | 1.444 (2) | C11X—H1XF | 0.9800 |
C5A—C6A | 1.358 (2) | C12X—H2XA | 0.9800 |
C5A—C51A | 1.473 (2) | C12X—H2XB | 0.9800 |
C51A—O51A | 1.217 (2) | C12X—H2XC | 0.9800 |
C51A—O52A | 1.330 (2) | C2X—O21X | 1.241 (2) |
O52A—H52A | 0.819 (16) | C2X—H2X | 0.9500 |
C6A—H6A | 0.9500 | ||
C6A—N1A—C2A | 123.30 (15) | C2X—N1X—C12X | 122.44 (15) |
C6A—N1A—H1A | 118.4 (14) | C11X—N1X—C12X | 117.25 (15) |
C2A—N1A—H1A | 118.2 (14) | N1X—C11X—H1XA | 109.5 |
N1A—C2A—N3A | 114.90 (15) | N1X—C11X—H1XB | 109.5 |
N1A—C2A—S21A | 121.85 (13) | H1XA—C11X—H1XB | 109.5 |
N3A—C2A—S21A | 123.25 (13) | N1X—C11X—H1XC | 109.5 |
C2A—N3A—C4A | 125.69 (15) | H1XA—C11X—H1XC | 109.5 |
C2A—N3A—H3A | 117.6 (13) | H1XB—C11X—H1XC | 109.5 |
C4A—N3A—H3A | 116.7 (13) | N1X—C11X—H1XD | 109.5 |
O41A—C4A—N3A | 120.17 (16) | N1X—C11X—H1XE | 109.5 |
O41A—C4A—C5A | 123.93 (15) | H1XD—C11X—H1XE | 109.5 |
N3A—C4A—C5A | 115.90 (14) | N1X—C11X—H1XF | 109.5 |
C6A—C5A—C4A | 118.31 (15) | H1XD—C11X—H1XF | 109.5 |
C6A—C5A—C51A | 120.33 (15) | H1XE—C11X—H1XF | 109.5 |
C4A—C5A—C51A | 121.34 (15) | N1X—C12X—H2XA | 109.5 |
O51A—C51A—O52A | 121.25 (15) | N1X—C12X—H2XB | 109.5 |
O51A—C51A—C5A | 122.51 (15) | H2XA—C12X—H2XB | 109.5 |
O52A—C51A—C5A | 116.24 (15) | N1X—C12X—H2XC | 109.5 |
C51A—O52A—H52A | 104.9 (16) | H2XA—C12X—H2XC | 109.5 |
N1A—C6A—C5A | 121.88 (16) | H2XB—C12X—H2XC | 109.5 |
N1A—C6A—H6A | 119.1 | O21X—C2X—N1X | 124.76 (17) |
C5A—C6A—H6A | 119.1 | O21X—C2X—H2X | 117.6 |
C2X—N1X—C11X | 120.29 (16) | N1X—C2X—H2X | 117.6 |
C6A—N1A—C2A—N3A | −0.1 (3) | C6A—C5A—C51A—O51A | −0.1 (3) |
C6A—N1A—C2A—S21A | −179.97 (14) | C4A—C5A—C51A—O51A | −178.61 (17) |
N1A—C2A—N3A—C4A | 1.4 (3) | C6A—C5A—C51A—O52A | −179.74 (16) |
S21A—C2A—N3A—C4A | −178.68 (14) | C4A—C5A—C51A—O52A | 1.7 (2) |
C2A—N3A—C4A—O41A | 177.08 (17) | C2A—N1A—C6A—C5A | −0.5 (3) |
C2A—N3A—C4A—C5A | −2.1 (3) | C4A—C5A—C6A—N1A | −0.2 (3) |
O41A—C4A—C5A—C6A | −177.76 (17) | C51A—C5A—C6A—N1A | −178.78 (16) |
N3A—C4A—C5A—C6A | 1.3 (2) | C11X—N1X—C2X—O21X | 1.1 (3) |
O41A—C4A—C5A—C51A | 0.8 (3) | C12X—N1X—C2X—O21X | −176.82 (18) |
N3A—C4A—C5A—C51A | 179.92 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O51Ai | 0.87 (2) | 1.92 (2) | 2.7846 (19) | 169 (2) |
N3A—H3A···O21X | 0.88 (2) | 1.84 (2) | 2.723 (2) | 179 (2) |
O52A—H52A···O41A | 0.82 (2) | 1.79 (2) | 2.5735 (18) | 159 (2) |
C6A—H6A···O52Ai | 0.95 | 2.53 | 3.269 (2) | 135 |
Symmetry code: (i) −x, y−1/2, −z+3/2. |
C5H4N2O3S·C2H6OS | Z = 2 |
Mr = 250.29 | F(000) = 260 |
Triclinic, P1 | Dx = 1.606 Mg m−3 |
a = 7.0475 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9534 (12) Å | Cell parameters from 5472 reflections |
c = 9.2802 (13) Å | θ = 3.5–26.1° |
α = 115.79 (1)° | µ = 0.51 mm−1 |
β = 95.753 (11)° | T = 173 K |
γ = 95.791 (10)° | Block, colourless |
V = 517.72 (13) Å3 | 0.30 × 0.25 × 0.15 mm |
Stoe IPDS II two-circle diffractometer | 1703 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.033 |
ω scans | θmax = 25.8°, θmin = 3.5° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −8→8 |
Tmin = 0.746, Tmax = 1.000 | k = −10→10 |
4538 measured reflections | l = −11→11 |
1976 independent reflections |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.037P)2 + 0.1288P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1976 reflections | Δρmax = 0.40 e Å−3 |
147 parameters | Δρmin = −0.23 e Å−3 |
C5H4N2O3S·C2H6OS | γ = 95.791 (10)° |
Mr = 250.29 | V = 517.72 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.0475 (9) Å | Mo Kα radiation |
b = 8.9534 (12) Å | µ = 0.51 mm−1 |
c = 9.2802 (13) Å | T = 173 K |
α = 115.79 (1)° | 0.30 × 0.25 × 0.15 mm |
β = 95.753 (11)° |
Stoe IPDS II two-circle diffractometer | 1976 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1703 reflections with I > 2σ(I) |
Tmin = 0.746, Tmax = 1.000 | Rint = 0.033 |
4538 measured reflections |
R[F2 > 2σ(F2)] = 0.027 | 3 restraints |
wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.40 e Å−3 |
1976 reflections | Δρmin = −0.23 e Å−3 |
147 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.59088 (19) | 0.20626 (17) | 0.58016 (17) | 0.0190 (3) | |
H1A | 0.486 (2) | 0.190 (2) | 0.619 (2) | 0.023* | |
C2A | 0.7581 (2) | 0.16694 (19) | 0.63431 (19) | 0.0172 (3) | |
S21A | 0.76313 (6) | 0.08217 (5) | 0.76181 (5) | 0.02329 (13) | |
N3A | 0.91866 (18) | 0.20414 (17) | 0.57701 (17) | 0.0191 (3) | |
H3A | 1.028 (2) | 0.190 (2) | 0.622 (2) | 0.023* | |
C4A | 0.9224 (2) | 0.2689 (2) | 0.4674 (2) | 0.0195 (3) | |
O41A | 1.07581 (17) | 0.29605 (16) | 0.42167 (16) | 0.0276 (3) | |
C5A | 0.7396 (2) | 0.3040 (2) | 0.4134 (2) | 0.0198 (3) | |
C51A | 0.7227 (3) | 0.3754 (2) | 0.2961 (2) | 0.0252 (4) | |
O51A | 0.57451 (19) | 0.41422 (17) | 0.25516 (17) | 0.0325 (3) | |
O52A | 0.8826 (2) | 0.39130 (18) | 0.23516 (17) | 0.0325 (3) | |
H52A | 0.969 (3) | 0.360 (3) | 0.277 (3) | 0.039* | |
C6A | 0.5815 (2) | 0.27235 (19) | 0.47463 (19) | 0.0187 (3) | |
H6A | 0.4615 | 0.2975 | 0.4422 | 0.022* | |
S1X | 0.35729 (5) | 0.25809 (5) | 0.89806 (5) | 0.01963 (12) | |
O11X | 0.27606 (15) | 0.17703 (15) | 0.71689 (14) | 0.0231 (3) | |
C11X | 0.2801 (3) | 0.1028 (2) | 0.9612 (2) | 0.0292 (4) | |
H1XA | 0.1411 | 0.0631 | 0.9236 | 0.044* | |
H1XB | 0.3063 | 0.1520 | 1.0798 | 0.044* | |
H1XC | 0.3504 | 0.0080 | 0.9148 | 0.044* | |
C12X | 0.2052 (2) | 0.4063 (2) | 0.9970 (2) | 0.0242 (4) | |
H2XA | 0.2178 | 0.4964 | 0.9638 | 0.036* | |
H2XB | 0.2436 | 0.4542 | 1.1147 | 0.036* | |
H2XC | 0.0706 | 0.3499 | 0.9669 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0131 (6) | 0.0245 (7) | 0.0213 (7) | 0.0031 (5) | 0.0023 (5) | 0.0121 (6) |
C2A | 0.0143 (7) | 0.0163 (7) | 0.0190 (8) | 0.0006 (6) | 0.0002 (6) | 0.0071 (6) |
S21A | 0.0185 (2) | 0.0291 (2) | 0.0289 (2) | 0.00175 (16) | 0.00037 (17) | 0.0202 (2) |
N3A | 0.0123 (6) | 0.0235 (7) | 0.0232 (7) | 0.0031 (5) | 0.0015 (5) | 0.0123 (6) |
C4A | 0.0181 (8) | 0.0175 (8) | 0.0202 (8) | 0.0015 (6) | 0.0045 (6) | 0.0060 (7) |
O41A | 0.0220 (6) | 0.0330 (7) | 0.0316 (7) | 0.0046 (5) | 0.0109 (5) | 0.0165 (6) |
C5A | 0.0215 (8) | 0.0185 (8) | 0.0178 (8) | 0.0020 (6) | 0.0006 (6) | 0.0074 (7) |
C51A | 0.0323 (9) | 0.0217 (8) | 0.0198 (9) | 0.0002 (7) | 0.0026 (7) | 0.0088 (7) |
O51A | 0.0356 (7) | 0.0371 (7) | 0.0305 (7) | 0.0059 (6) | −0.0022 (6) | 0.0220 (6) |
O52A | 0.0388 (8) | 0.0384 (8) | 0.0288 (7) | 0.0062 (6) | 0.0116 (6) | 0.0217 (6) |
C6A | 0.0176 (7) | 0.0184 (7) | 0.0181 (8) | 0.0030 (6) | −0.0011 (6) | 0.0070 (7) |
S1X | 0.01389 (19) | 0.0265 (2) | 0.0205 (2) | 0.00437 (15) | 0.00238 (15) | 0.01223 (17) |
O11X | 0.0148 (5) | 0.0362 (7) | 0.0191 (6) | 0.0045 (5) | 0.0016 (5) | 0.0134 (5) |
C11X | 0.0338 (9) | 0.0280 (9) | 0.0302 (10) | 0.0053 (8) | −0.0005 (8) | 0.0181 (8) |
C12X | 0.0228 (8) | 0.0256 (8) | 0.0265 (9) | 0.0075 (7) | 0.0058 (7) | 0.0127 (7) |
N1A—C6A | 1.346 (2) | C51A—O52A | 1.332 (2) |
N1A—C2A | 1.372 (2) | O52A—H52A | 0.825 (16) |
N1A—H1A | 0.883 (15) | C6A—H6A | 0.9500 |
C2A—N3A | 1.369 (2) | S1X—O11X | 1.5306 (12) |
C2A—S21A | 1.6600 (16) | S1X—C12X | 1.7823 (17) |
N3A—C4A | 1.374 (2) | S1X—C11X | 1.7871 (18) |
N3A—H3A | 0.886 (15) | C11X—H1XA | 0.9800 |
C4A—O41A | 1.239 (2) | C11X—H1XB | 0.9800 |
C4A—C5A | 1.449 (2) | C11X—H1XC | 0.9800 |
C5A—C6A | 1.359 (2) | C12X—H2XA | 0.9800 |
C5A—C51A | 1.485 (2) | C12X—H2XB | 0.9800 |
C51A—O51A | 1.210 (2) | C12X—H2XC | 0.9800 |
C6A—N1A—C2A | 123.20 (14) | N1A—C6A—C5A | 121.57 (14) |
C6A—N1A—H1A | 119.0 (13) | N1A—C6A—H6A | 119.2 |
C2A—N1A—H1A | 117.8 (13) | C5A—C6A—H6A | 119.2 |
N3A—C2A—N1A | 115.25 (14) | O11X—S1X—C12X | 106.23 (8) |
N3A—C2A—S21A | 122.94 (12) | O11X—S1X—C11X | 104.29 (8) |
N1A—C2A—S21A | 121.81 (12) | C12X—S1X—C11X | 98.50 (9) |
C2A—N3A—C4A | 125.63 (13) | S1X—C11X—H1XA | 109.5 |
C2A—N3A—H3A | 114.8 (13) | S1X—C11X—H1XB | 109.5 |
C4A—N3A—H3A | 119.4 (13) | H1XA—C11X—H1XB | 109.5 |
O41A—C4A—N3A | 120.45 (14) | S1X—C11X—H1XC | 109.5 |
O41A—C4A—C5A | 123.73 (15) | H1XA—C11X—H1XC | 109.5 |
N3A—C4A—C5A | 115.81 (14) | H1XB—C11X—H1XC | 109.5 |
C6A—C5A—C4A | 118.48 (15) | S1X—C12X—H2XA | 109.5 |
C6A—C5A—C51A | 119.91 (14) | S1X—C12X—H2XB | 109.5 |
C4A—C5A—C51A | 121.60 (15) | H2XA—C12X—H2XB | 109.5 |
O51A—C51A—O52A | 121.60 (16) | S1X—C12X—H2XC | 109.5 |
O51A—C51A—C5A | 123.16 (16) | H2XA—C12X—H2XC | 109.5 |
O52A—C51A—C5A | 115.22 (15) | H2XB—C12X—H2XC | 109.5 |
C51A—O52A—H52A | 108.5 (17) | ||
C6A—N1A—C2A—N3A | 1.8 (2) | N3A—C4A—C5A—C51A | 179.53 (15) |
C6A—N1A—C2A—S21A | −178.80 (12) | C6A—C5A—C51A—O51A | 3.0 (3) |
N1A—C2A—N3A—C4A | −3.0 (2) | C4A—C5A—C51A—O51A | −176.02 (17) |
S21A—C2A—N3A—C4A | 177.66 (13) | C6A—C5A—C51A—O52A | −175.72 (15) |
C2A—N3A—C4A—O41A | −179.03 (15) | C4A—C5A—C51A—O52A | 5.3 (2) |
C2A—N3A—C4A—C5A | 1.8 (2) | C2A—N1A—C6A—C5A | 0.4 (2) |
O41A—C4A—C5A—C6A | −178.59 (16) | C4A—C5A—C6A—N1A | −1.6 (2) |
N3A—C4A—C5A—C6A | 0.5 (2) | C51A—C5A—C6A—N1A | 179.42 (15) |
O41A—C4A—C5A—C51A | 0.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O11X | 0.88 (2) | 1.83 (2) | 2.7087 (17) | 174 (2) |
N3A—H3A···O11Xi | 0.89 (2) | 1.92 (2) | 2.7983 (18) | 175 (2) |
O52A—H52A···O41A | 0.83 (2) | 1.80 (2) | 2.5738 (19) | 155 (2) |
Symmetry code: (i) x+1, y, z. |
C5H4N2O3S·1.5C4H8O2 | Z = 2 |
Mr = 304.32 | F(000) = 320 |
Triclinic, P1 | Dx = 1.459 Mg m−3 |
a = 5.2819 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3542 (12) Å | Cell parameters from 6794 reflections |
c = 13.0071 (15) Å | θ = 3.7–26.1° |
α = 89.377 (10)° | µ = 0.26 mm−1 |
β = 85.143 (10)° | T = 173 K |
γ = 77.70 (1)° | Block, colourless |
V = 692.51 (15) Å3 | 0.30 × 0.21 × 0.16 mm |
Stoe IPDS II two-circle diffractometer | 2272 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.045 |
ω scans | θmax = 25.8°, θmin = 3.7° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −6→5 |
Tmin = 0.528, Tmax = 1.000 | k = −12→12 |
5885 measured reflections | l = −15→15 |
2645 independent reflections |
Refinement on F2 | 3 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.0652P)2 + 0.0475P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2645 reflections | Δρmax = 0.30 e Å−3 |
190 parameters | Δρmin = −0.22 e Å−3 |
C5H4N2O3S·1.5C4H8O2 | γ = 77.70 (1)° |
Mr = 304.32 | V = 692.51 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.2819 (7) Å | Mo Kα radiation |
b = 10.3542 (12) Å | µ = 0.26 mm−1 |
c = 13.0071 (15) Å | T = 173 K |
α = 89.377 (10)° | 0.30 × 0.21 × 0.16 mm |
β = 85.143 (10)° |
Stoe IPDS II two-circle diffractometer | 2645 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 2272 reflections with I > 2σ(I) |
Tmin = 0.528, Tmax = 1.000 | Rint = 0.045 |
5885 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 3 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.30 e Å−3 |
2645 reflections | Δρmin = −0.22 e Å−3 |
190 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.5758 (3) | 0.33844 (13) | 0.12070 (9) | 0.0232 (3) | |
H1A | 0.597 (4) | 0.2659 (16) | 0.0860 (13) | 0.028* | |
C2A | 0.7455 (3) | 0.34583 (15) | 0.19351 (11) | 0.0227 (3) | |
S21A | 0.99858 (8) | 0.22538 (4) | 0.21249 (3) | 0.03074 (15) | |
N3A | 0.6876 (3) | 0.46087 (13) | 0.25010 (9) | 0.0241 (3) | |
H3A | 0.799 (4) | 0.4702 (19) | 0.2964 (13) | 0.029* | |
C4A | 0.4821 (3) | 0.56608 (15) | 0.23970 (11) | 0.0233 (3) | |
O41A | 0.4540 (2) | 0.66521 (11) | 0.29541 (8) | 0.0308 (3) | |
C5A | 0.3104 (3) | 0.54962 (15) | 0.16168 (11) | 0.0226 (3) | |
C51A | 0.0737 (3) | 0.65151 (15) | 0.14615 (12) | 0.0265 (3) | |
O51A | −0.0751 (2) | 0.64100 (12) | 0.08219 (9) | 0.0360 (3) | |
O52A | 0.0287 (2) | 0.75760 (12) | 0.20765 (9) | 0.0326 (3) | |
H52A | 0.150 (4) | 0.744 (2) | 0.2446 (15) | 0.039* | |
C6A | 0.3660 (3) | 0.43494 (15) | 0.10612 (11) | 0.0228 (3) | |
H6A | 0.2536 | 0.4224 | 0.0555 | 0.027* | |
O1X | 1.0271 (2) | 0.50814 (11) | 0.39123 (8) | 0.0307 (3) | |
C2X | 0.9442 (4) | 0.62568 (16) | 0.45447 (12) | 0.0322 (4) | |
H2X1 | 0.8250 | 0.6936 | 0.4173 | 0.039* | |
H2X2 | 1.0972 | 0.6618 | 0.4683 | 0.039* | |
C6X | 1.1922 (3) | 0.40586 (17) | 0.44515 (12) | 0.0316 (4) | |
H6X1 | 1.3530 | 0.4350 | 0.4589 | 0.038* | |
H6X2 | 1.2422 | 0.3253 | 0.4014 | 0.038* | |
O1Y | 0.3820 (3) | 0.89102 (14) | 0.48933 (12) | 0.0525 (4) | |
C2Y | 0.3206 (5) | 0.9769 (2) | 0.57690 (18) | 0.0567 (6) | |
H2Y1 | 0.2734 | 0.9266 | 0.6381 | 0.068* | |
H2Y2 | 0.1687 | 1.0481 | 0.5648 | 0.068* | |
C6Y | 0.4550 (5) | 0.9636 (2) | 0.40253 (17) | 0.0551 (6) | |
H6Y1 | 0.3057 | 1.0345 | 0.3868 | 0.066* | |
H6Y2 | 0.5032 | 0.9041 | 0.3417 | 0.066* | |
O1Z | 0.6295 (2) | 0.10460 (10) | 0.01198 (8) | 0.0282 (3) | |
C2Z | 0.7012 (3) | −0.01927 (15) | 0.06553 (13) | 0.0291 (3) | |
H2Z1 | 0.7668 | −0.0032 | 0.1323 | 0.035* | |
H2Z2 | 0.8423 | −0.0795 | 0.0238 | 0.035* | |
C6Z | 0.5295 (3) | 0.08283 (15) | −0.08431 (12) | 0.0272 (3) | |
H6Z1 | 0.6668 | 0.0249 | −0.1294 | 0.033* | |
H6Z2 | 0.4771 | 0.1682 | −0.1198 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0238 (7) | 0.0216 (6) | 0.0248 (6) | −0.0050 (5) | −0.0047 (5) | −0.0034 (5) |
C2A | 0.0215 (7) | 0.0232 (7) | 0.0241 (7) | −0.0066 (6) | −0.0022 (6) | 0.0019 (5) |
S21A | 0.0265 (2) | 0.0259 (2) | 0.0388 (2) | −0.00069 (16) | −0.00924 (17) | −0.00132 (16) |
N3A | 0.0231 (7) | 0.0248 (7) | 0.0252 (6) | −0.0047 (5) | −0.0079 (5) | −0.0030 (5) |
C4A | 0.0234 (8) | 0.0230 (7) | 0.0244 (7) | −0.0066 (6) | −0.0030 (6) | −0.0002 (6) |
O41A | 0.0316 (6) | 0.0265 (6) | 0.0343 (6) | −0.0035 (5) | −0.0089 (5) | −0.0080 (5) |
C5A | 0.0222 (8) | 0.0235 (7) | 0.0229 (7) | −0.0059 (6) | −0.0038 (6) | 0.0016 (5) |
C51A | 0.0260 (8) | 0.0240 (8) | 0.0291 (7) | −0.0045 (6) | −0.0029 (6) | 0.0017 (6) |
O51A | 0.0315 (7) | 0.0350 (7) | 0.0401 (6) | 0.0015 (5) | −0.0169 (5) | −0.0025 (5) |
O52A | 0.0300 (7) | 0.0274 (6) | 0.0384 (6) | 0.0015 (5) | −0.0102 (5) | −0.0033 (5) |
C6A | 0.0219 (8) | 0.0250 (7) | 0.0230 (7) | −0.0074 (6) | −0.0045 (6) | 0.0016 (5) |
O1X | 0.0372 (7) | 0.0316 (6) | 0.0241 (5) | −0.0054 (5) | −0.0110 (5) | −0.0022 (4) |
C2X | 0.0395 (10) | 0.0270 (8) | 0.0308 (8) | −0.0048 (7) | −0.0132 (7) | −0.0026 (6) |
C6X | 0.0293 (9) | 0.0339 (9) | 0.0313 (8) | −0.0022 (7) | −0.0113 (7) | −0.0052 (6) |
O1Y | 0.0603 (10) | 0.0385 (8) | 0.0635 (9) | −0.0206 (7) | −0.0080 (8) | −0.0012 (7) |
C2Y | 0.0662 (15) | 0.0474 (12) | 0.0568 (12) | −0.0180 (11) | 0.0082 (11) | 0.0001 (10) |
C6Y | 0.0744 (16) | 0.0448 (12) | 0.0495 (11) | −0.0152 (11) | −0.0172 (11) | 0.0015 (9) |
O1Z | 0.0283 (6) | 0.0201 (5) | 0.0380 (6) | −0.0059 (4) | −0.0109 (5) | −0.0014 (4) |
C2Z | 0.0287 (8) | 0.0220 (7) | 0.0377 (8) | −0.0041 (6) | −0.0123 (7) | 0.0004 (6) |
C6Z | 0.0273 (8) | 0.0233 (8) | 0.0305 (7) | −0.0030 (6) | −0.0044 (6) | −0.0016 (6) |
N1A—C6A | 1.350 (2) | C6X—C2Xi | 1.504 (3) |
N1A—C2A | 1.3716 (19) | C6X—H6X1 | 0.9900 |
N1A—H1A | 0.862 (15) | C6X—H6X2 | 0.9900 |
C2A—N3A | 1.371 (2) | O1Y—C6Y | 1.421 (3) |
C2A—S21A | 1.6559 (15) | O1Y—C2Y | 1.425 (3) |
N3A—C4A | 1.379 (2) | C2Y—C6Yii | 1.491 (4) |
N3A—H3A | 0.898 (14) | C2Y—H2Y1 | 0.9900 |
C4A—O41A | 1.2385 (19) | C2Y—H2Y2 | 0.9900 |
C4A—C5A | 1.451 (2) | C6Y—C2Yii | 1.491 (4) |
C5A—C6A | 1.361 (2) | C6Y—H6Y1 | 0.9900 |
C5A—C51A | 1.481 (2) | C6Y—H6Y2 | 0.9900 |
C51A—O51A | 1.2131 (19) | O1Z—C6Z | 1.4379 (18) |
C51A—O52A | 1.334 (2) | O1Z—C2Z | 1.4464 (18) |
O52A—H52A | 0.821 (16) | C2Z—C6Ziii | 1.505 (2) |
C6A—H6A | 0.9500 | C2Z—H2Z1 | 0.9900 |
O1X—C6X | 1.4379 (19) | C2Z—H2Z2 | 0.9900 |
O1X—C2X | 1.443 (2) | C6Z—C2Ziii | 1.505 (2) |
C2X—C6Xi | 1.504 (3) | C6Z—H6Z1 | 0.9900 |
C2X—H2X1 | 0.9900 | C6Z—H6Z2 | 0.9900 |
C2X—H2X2 | 0.9900 | ||
C6A—N1A—C2A | 123.32 (13) | C2Xi—C6X—H6X1 | 109.5 |
C6A—N1A—H1A | 118.1 (13) | O1X—C6X—H6X2 | 109.5 |
C2A—N1A—H1A | 118.3 (13) | C2Xi—C6X—H6X2 | 109.5 |
N3A—C2A—N1A | 114.52 (13) | H6X1—C6X—H6X2 | 108.0 |
N3A—C2A—S21A | 122.58 (11) | C6Y—O1Y—C2Y | 108.89 (16) |
N1A—C2A—S21A | 122.90 (12) | O1Y—C2Y—C6Yii | 111.2 (2) |
C2A—N3A—C4A | 126.59 (13) | O1Y—C2Y—H2Y1 | 109.4 |
C2A—N3A—H3A | 116.6 (13) | C6Yii—C2Y—H2Y1 | 109.4 |
C4A—N3A—H3A | 116.8 (12) | O1Y—C2Y—H2Y2 | 109.4 |
O41A—C4A—N3A | 119.91 (13) | C6Yii—C2Y—H2Y2 | 109.4 |
O41A—C4A—C5A | 124.74 (14) | H2Y1—C2Y—H2Y2 | 108.0 |
N3A—C4A—C5A | 115.34 (13) | O1Y—C6Y—C2Yii | 110.69 (18) |
C6A—C5A—C4A | 118.19 (14) | O1Y—C6Y—H6Y1 | 109.5 |
C6A—C5A—C51A | 120.59 (13) | C2Yii—C6Y—H6Y1 | 109.5 |
C4A—C5A—C51A | 121.15 (13) | O1Y—C6Y—H6Y2 | 109.5 |
O51A—C51A—O52A | 120.62 (15) | C2Yii—C6Y—H6Y2 | 109.5 |
O51A—C51A—C5A | 123.09 (14) | H6Y1—C6Y—H6Y2 | 108.1 |
O52A—C51A—C5A | 116.30 (13) | C6Z—O1Z—C2Z | 110.04 (11) |
C51A—O52A—H52A | 104.6 (15) | O1Z—C2Z—C6Ziii | 110.44 (13) |
N1A—C6A—C5A | 122.02 (13) | O1Z—C2Z—H2Z1 | 109.6 |
N1A—C6A—H6A | 119.0 | C6Ziii—C2Z—H2Z1 | 109.6 |
C5A—C6A—H6A | 119.0 | O1Z—C2Z—H2Z2 | 109.6 |
C6X—O1X—C2X | 110.73 (11) | C6Ziii—C2Z—H2Z2 | 109.6 |
O1X—C2X—C6Xi | 110.26 (14) | H2Z1—C2Z—H2Z2 | 108.1 |
O1X—C2X—H2X1 | 109.6 | O1Z—C6Z—C2Ziii | 110.14 (13) |
C6Xi—C2X—H2X1 | 109.6 | O1Z—C6Z—H6Z1 | 109.6 |
O1X—C2X—H2X2 | 109.6 | C2Ziii—C6Z—H6Z1 | 109.6 |
C6Xi—C2X—H2X2 | 109.6 | O1Z—C6Z—H6Z2 | 109.6 |
H2X1—C2X—H2X2 | 108.1 | C2Ziii—C6Z—H6Z2 | 109.6 |
O1X—C6X—C2Xi | 110.90 (14) | H6Z1—C6Z—H6Z2 | 108.1 |
O1X—C6X—H6X1 | 109.5 | ||
C6A—N1A—C2A—N3A | −0.9 (2) | C6A—C5A—C51A—O52A | 176.76 (14) |
C6A—N1A—C2A—S21A | 178.59 (11) | C4A—C5A—C51A—O52A | −0.2 (2) |
N1A—C2A—N3A—C4A | −0.6 (2) | C2A—N1A—C6A—C5A | 1.7 (2) |
S21A—C2A—N3A—C4A | 179.93 (12) | C4A—C5A—C6A—N1A | −0.9 (2) |
C2A—N3A—C4A—O41A | −179.16 (14) | C51A—C5A—C6A—N1A | −177.92 (13) |
C2A—N3A—C4A—C5A | 1.2 (2) | C6X—O1X—C2X—C6Xi | −56.90 (19) |
O41A—C4A—C5A—C6A | 179.95 (14) | C2X—O1X—C6X—C2Xi | 57.26 (19) |
N3A—C4A—C5A—C6A | −0.4 (2) | C6Y—O1Y—C2Y—C6Yii | −57.8 (3) |
O41A—C4A—C5A—C51A | −3.1 (2) | C2Y—O1Y—C6Y—C2Yii | 57.5 (3) |
N3A—C4A—C5A—C51A | 176.56 (13) | C6Z—O1Z—C2Z—C6Ziii | −58.19 (18) |
C6A—C5A—C51A—O51A | −2.7 (2) | C2Z—O1Z—C6Z—C2Ziii | 58.01 (18) |
C4A—C5A—C51A—O51A | −179.58 (15) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6A···O51Aiv | 0.95 | 2.26 | 3.1892 (18) | 166 |
N1A—H1A···O1Z | 0.86 (2) | 1.91 (2) | 2.7670 (17) | 178 (2) |
N3A—H3A···O1X | 0.90 (1) | 1.89 (2) | 2.7889 (17) | 174 (2) |
O52A—H52A···O41A | 0.82 (2) | 1.81 (2) | 2.5998 (16) | 160 (2) |
Symmetry code: (iv) −x, −y+1, −z. |
C5H4N2O3S | F(000) = 704 |
Mr = 172.16 | Dx = 1.765 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.409 (3) Å | Cell parameters from 5588 reflections |
b = 15.552 (3) Å | θ = 3.4–26.0° |
c = 7.369 (2) Å | µ = 0.45 mm−1 |
β = 97.599 (19)° | T = 173 K |
V = 1296.0 (6) Å3 | Block, colourless |
Z = 8 | 0.25 × 0.11 × 0.08 mm |
Stoe IPDS II two-circle diffractometer | 1294 reflections with I > 2σ(I) |
Radiation source: Genix 3D IµS microfocus X-ray source | Rint = 0.149 |
ω scans | θmax = 26.0°, θmin = 3.4° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −11→14 |
Tmin = 0.149, Tmax = 1.000 | k = −19→19 |
9985 measured reflections | l = −9→8 |
2492 independent reflections |
Refinement on F2 | 6 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.164 | w = 1/[σ2(Fo2) + (0.0547P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
2492 reflections | Δρmax = 0.61 e Å−3 |
217 parameters | Δρmin = −0.32 e Å−3 |
C5H4N2O3S | V = 1296.0 (6) Å3 |
Mr = 172.16 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.409 (3) Å | µ = 0.45 mm−1 |
b = 15.552 (3) Å | T = 173 K |
c = 7.369 (2) Å | 0.25 × 0.11 × 0.08 mm |
β = 97.599 (19)° |
Stoe IPDS II two-circle diffractometer | 2492 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1294 reflections with I > 2σ(I) |
Tmin = 0.149, Tmax = 1.000 | Rint = 0.149 |
9985 measured reflections |
R[F2 > 2σ(F2)] = 0.077 | 6 restraints |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.61 e Å−3 |
2492 reflections | Δρmin = −0.32 e Å−3 |
217 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.4523 (5) | 0.8214 (3) | 0.1538 (7) | 0.0364 (14) | |
H1A | 0.519 (4) | 0.806 (4) | 0.219 (8) | 0.044* | |
C2A | 0.3863 (6) | 0.7515 (4) | 0.0896 (8) | 0.0342 (15) | |
S21A | 0.43438 (16) | 0.65141 (11) | 0.1289 (2) | 0.0379 (5) | |
N3A | 0.2805 (5) | 0.7715 (3) | −0.0096 (8) | 0.0376 (14) | |
H3A | 0.231 (5) | 0.731 (3) | −0.053 (9) | 0.045* | |
C4A | 0.2361 (6) | 0.8537 (4) | −0.0597 (9) | 0.0340 (15) | |
O41A | 0.1442 (4) | 0.8588 (3) | −0.1625 (7) | 0.0466 (13) | |
C5A | 0.3096 (6) | 0.9227 (4) | 0.0265 (8) | 0.0337 (16) | |
C51A | 0.2765 (7) | 1.0147 (4) | 0.0136 (8) | 0.0357 (16) | |
O51A | 0.3435 (5) | 1.0694 (3) | 0.0922 (7) | 0.0500 (14) | |
O52A | 0.1736 (4) | 1.0341 (3) | −0.0812 (6) | 0.0449 (13) | |
H52A | 0.155 (7) | 1.0864 (18) | −0.090 (10) | 0.054* | |
C6A | 0.4124 (6) | 0.9036 (4) | 0.1289 (8) | 0.0323 (16) | |
H6A | 0.4591 | 0.9491 | 0.1862 | 0.039* | |
N1B | 0.0603 (5) | 0.4502 (3) | −0.1906 (8) | 0.0376 (14) | |
H1B | −0.001 (4) | 0.460 (4) | −0.272 (7) | 0.045* | |
C2B | 0.1251 (6) | 0.5209 (4) | −0.1303 (8) | 0.0340 (16) | |
S21B | 0.08396 (16) | 0.62065 (10) | −0.1902 (2) | 0.0395 (5) | |
N3B | 0.2257 (5) | 0.5011 (3) | −0.0177 (7) | 0.0363 (14) | |
H3B | 0.266 (5) | 0.545 (3) | 0.029 (8) | 0.044* | |
C4B | 0.2689 (6) | 0.4203 (4) | 0.0411 (9) | 0.0337 (16) | |
O41B | 0.3576 (4) | 0.4154 (3) | 0.1522 (7) | 0.0463 (14) | |
C5B | 0.1964 (6) | 0.3496 (4) | −0.0393 (9) | 0.0348 (16) | |
C51B | 0.2222 (6) | 0.2579 (4) | −0.0058 (9) | 0.0403 (18) | |
O51B | 0.1522 (5) | 0.2029 (3) | −0.0751 (8) | 0.0566 (16) | |
O52B | 0.3212 (4) | 0.2395 (3) | 0.0942 (7) | 0.0436 (13) | |
H52B | 0.327 (7) | 0.1851 (14) | 0.097 (10) | 0.052* | |
C6B | 0.0945 (6) | 0.3694 (4) | −0.1497 (8) | 0.0395 (18) | |
H6B | 0.0453 | 0.3237 | −0.2000 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.031 (3) | 0.033 (3) | 0.041 (3) | −0.001 (2) | −0.012 (3) | 0.001 (2) |
C2A | 0.037 (4) | 0.037 (4) | 0.030 (3) | 0.004 (3) | 0.009 (3) | −0.001 (3) |
S21A | 0.0341 (10) | 0.0302 (9) | 0.0464 (10) | 0.0019 (7) | −0.0058 (8) | 0.0022 (7) |
N3A | 0.039 (4) | 0.025 (3) | 0.045 (3) | 0.000 (2) | −0.008 (3) | −0.001 (2) |
C4A | 0.029 (4) | 0.035 (4) | 0.037 (4) | 0.003 (3) | 0.000 (3) | 0.003 (3) |
O41A | 0.034 (3) | 0.035 (3) | 0.064 (3) | 0.003 (2) | −0.021 (3) | 0.000 (2) |
C5A | 0.041 (4) | 0.032 (4) | 0.029 (4) | 0.001 (3) | 0.005 (3) | −0.001 (3) |
C51A | 0.041 (4) | 0.033 (4) | 0.033 (4) | −0.002 (3) | 0.002 (3) | 0.000 (3) |
O51A | 0.052 (4) | 0.031 (3) | 0.061 (3) | −0.003 (2) | −0.013 (3) | −0.001 (2) |
O52A | 0.039 (3) | 0.036 (3) | 0.055 (3) | 0.005 (2) | −0.010 (3) | 0.004 (2) |
C6A | 0.035 (4) | 0.026 (3) | 0.034 (3) | −0.002 (3) | −0.002 (3) | 0.001 (2) |
N1B | 0.032 (4) | 0.033 (3) | 0.043 (3) | −0.002 (3) | −0.010 (3) | 0.005 (2) |
C2B | 0.035 (4) | 0.033 (4) | 0.034 (3) | −0.005 (3) | 0.005 (3) | −0.003 (3) |
S21B | 0.0363 (10) | 0.0305 (9) | 0.0489 (10) | 0.0019 (7) | −0.0052 (8) | 0.0028 (7) |
N3B | 0.035 (4) | 0.029 (3) | 0.042 (3) | −0.002 (3) | −0.007 (3) | −0.002 (2) |
C4B | 0.034 (4) | 0.038 (4) | 0.030 (4) | 0.004 (3) | 0.009 (3) | −0.004 (3) |
O41B | 0.038 (3) | 0.035 (3) | 0.060 (3) | 0.005 (2) | −0.017 (3) | −0.003 (2) |
C5B | 0.035 (4) | 0.023 (3) | 0.043 (4) | −0.001 (3) | −0.007 (3) | −0.003 (3) |
C51B | 0.028 (4) | 0.038 (4) | 0.052 (4) | 0.002 (3) | −0.008 (4) | −0.002 (3) |
O51B | 0.049 (4) | 0.027 (3) | 0.085 (4) | −0.001 (2) | −0.024 (3) | −0.006 (2) |
O52B | 0.038 (3) | 0.027 (3) | 0.060 (3) | 0.003 (2) | −0.015 (3) | 0.002 (2) |
C6B | 0.040 (4) | 0.038 (4) | 0.038 (4) | 0.002 (3) | −0.004 (4) | −0.001 (3) |
N1A—C6A | 1.360 (8) | N1B—C6B | 1.338 (8) |
N1A—C2A | 1.371 (8) | N1B—C2B | 1.367 (8) |
N1A—H1A | 0.88 (2) | N1B—H1B | 0.87 (2) |
C2A—N3A | 1.362 (9) | C2B—N3B | 1.359 (9) |
C2A—S21A | 1.663 (6) | C2B—S21B | 1.663 (7) |
N3A—C4A | 1.407 (8) | N3B—C4B | 1.397 (8) |
N3A—H3A | 0.87 (2) | N3B—H3B | 0.87 (2) |
C4A—O41A | 1.212 (7) | C4B—O41B | 1.217 (8) |
C4A—C5A | 1.455 (9) | C4B—C5B | 1.455 (9) |
C5A—C6A | 1.342 (9) | C5B—C6B | 1.363 (9) |
C5A—C51A | 1.479 (9) | C5B—C51B | 1.469 (9) |
C51A—O51A | 1.236 (8) | C51B—O51B | 1.234 (8) |
C51A—O52A | 1.319 (8) | C51B—O52B | 1.296 (8) |
O52A—H52A | 0.84 (2) | O52B—H52B | 0.85 (2) |
C6A—H6A | 0.9500 | C6B—H6B | 0.9500 |
C6A—N1A—C2A | 122.7 (6) | C6B—N1B—C2B | 123.6 (6) |
C6A—N1A—H1A | 125 (4) | C6B—N1B—H1B | 120 (5) |
C2A—N1A—H1A | 112 (4) | C2B—N1B—H1B | 115 (5) |
N3A—C2A—N1A | 114.3 (5) | N3B—C2B—N1B | 113.1 (5) |
N3A—C2A—S21A | 123.8 (5) | N3B—C2B—S21B | 124.1 (5) |
N1A—C2A—S21A | 122.0 (5) | N1B—C2B—S21B | 122.9 (5) |
C2A—N3A—C4A | 127.7 (5) | C2B—N3B—C4B | 129.0 (5) |
C2A—N3A—H3A | 121 (5) | C2B—N3B—H3B | 115 (5) |
C4A—N3A—H3A | 111 (5) | C4B—N3B—H3B | 116 (5) |
O41A—C4A—N3A | 118.4 (6) | O41B—C4B—N3B | 119.6 (6) |
O41A—C4A—C5A | 128.7 (6) | O41B—C4B—C5B | 127.1 (6) |
N3A—C4A—C5A | 112.9 (5) | N3B—C4B—C5B | 113.3 (6) |
C6A—C5A—C4A | 119.5 (6) | C6B—C5B—C4B | 117.8 (6) |
C6A—C5A—C51A | 116.6 (6) | C6B—C5B—C51B | 117.1 (5) |
C4A—C5A—C51A | 123.9 (6) | C4B—C5B—C51B | 125.0 (6) |
O51A—C51A—O52A | 122.9 (6) | O51B—C51B—O52B | 123.3 (6) |
O51A—C51A—C5A | 119.9 (6) | O51B—C51B—C5B | 119.9 (6) |
O52A—C51A—C5A | 117.1 (6) | O52B—C51B—C5B | 116.8 (6) |
C51A—O52A—H52A | 117 (5) | C51B—O52B—H52B | 107 (5) |
C5A—C6A—N1A | 122.4 (6) | N1B—C6B—C5B | 123.2 (6) |
C5A—C6A—H6A | 118.8 | N1B—C6B—H6B | 118.4 |
N1A—C6A—H6A | 118.8 | C5B—C6B—H6B | 118.4 |
C6A—N1A—C2A—N3A | 3.5 (9) | C6B—N1B—C2B—N3B | −2.7 (10) |
C6A—N1A—C2A—S21A | −177.4 (6) | C6B—N1B—C2B—S21B | 177.2 (6) |
N1A—C2A—N3A—C4A | 3.6 (10) | N1B—C2B—N3B—C4B | 0.1 (10) |
S21A—C2A—N3A—C4A | −175.5 (5) | S21B—C2B—N3B—C4B | −179.8 (6) |
C2A—N3A—C4A—O41A | 173.5 (7) | C2B—N3B—C4B—O41B | −175.3 (7) |
C2A—N3A—C4A—C5A | −7.7 (10) | C2B—N3B—C4B—C5B | 3.1 (10) |
O41A—C4A—C5A—C6A | −176.3 (7) | O41B—C4B—C5B—C6B | 174.4 (7) |
N3A—C4A—C5A—C6A | 5.0 (9) | N3B—C4B—C5B—C6B | −3.8 (9) |
O41A—C4A—C5A—C51A | 5.7 (12) | O41B—C4B—C5B—C51B | −3.4 (12) |
N3A—C4A—C5A—C51A | −173.0 (7) | N3B—C4B—C5B—C51B | 178.4 (6) |
C6A—C5A—C51A—O51A | 1.3 (10) | C6B—C5B—C51B—O51B | −0.8 (11) |
C4A—C5A—C51A—O51A | 179.4 (7) | C4B—C5B—C51B—O51B | 177.0 (7) |
C6A—C5A—C51A—O52A | −177.6 (6) | C6B—C5B—C51B—O52B | 177.7 (7) |
C4A—C5A—C51A—O52A | 0.5 (10) | C4B—C5B—C51B—O52B | −4.5 (10) |
C4A—C5A—C6A—N1A | 1.0 (11) | C2B—N1B—C6B—C5B | 1.8 (11) |
C51A—C5A—C6A—N1A | 179.2 (6) | C4B—C5B—C6B—N1B | 1.8 (11) |
C2A—N1A—C6A—C5A | −5.8 (11) | C51B—C5B—C6B—N1B | 179.7 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O52Bi | 0.88 (2) | 2.38 (3) | 3.239 (7) | 168 (6) |
N1B—H1B···O52Aii | 0.87 (2) | 2.41 (3) | 3.235 (7) | 158 (6) |
N3A—H3A···S21B | 0.87 (2) | 2.52 (2) | 3.393 (6) | 177 (6) |
N3B—H3B···S21A | 0.87 (2) | 2.57 (3) | 3.409 (6) | 163 (6) |
O52A—H52A···O51Biii | 0.84 (2) | 1.82 (3) | 2.639 (6) | 165 (8) |
O52B—H52B···O51Aiv | 0.85 (2) | 1.81 (2) | 2.657 (6) | 177 (8) |
N1A—H1A···O41Bi | 0.88 (2) | 2.32 (6) | 2.840 (7) | 118 (5) |
C6A—H6A···O41Bi | 0.95 | 2.32 | 2.898 (8) | 118 |
N1B—H1B···O41Aii | 0.87 (2) | 2.27 (6) | 2.822 (7) | 121 (6) |
C6B—H6B···O41Aii | 0.95 | 2.33 | 2.891 (8) | 117 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z−1/2; (iii) x, y+1, z; (iv) x, y−1, z. |
Crystal | Amount (mg, mmol) | Solvent |
(I) | 2.4, 0.017 | H2O (200 µl) |
(II) | 1.9, 0.012 | DMF (50 µl) |
(III) | 2.7, 0.017 | DMSO (50 µl) |
(IV) | 2.2, 0.014 | DMAC (25 µl) |
(V) | 2.3, 0.013 | DMF (25 µl) |
(VI) | 2.6, 0.015 | DMSO (25 µl) |
(VII) | 2.3, 0.013 | Dioxane (300 µl) |
(VIII) | 2.0, 0.012 | Methanol (500 µl) |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C5H6N2O3 | C5H4N2O4·C3H7NO | C5H4N2O4·C2H6OS | C5H4N2O4·C4H9NO |
Mr | 142.12 | 229.20 | 234.23 | 243.22 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 173 | 173 | 173 | 173 |
a, b, c (Å) | 4.874 (3), 7.663 (2), 8.325 (3) | 8.671 (3), 12.394 (2), 9.381 (2) | 6.9341 (9), 6.9015 (5), 20.919 (3) | 11.7707 (19), 6.1053 (10), 15.271 (3) |
α, β, γ (°) | 66.97 (2), 88.09 (2), 87.07 (2) | 90, 90.17 (2), 90 | 90, 96.604 (10), 90 | 90, 90.858 (13), 90 |
V (Å3) | 285.7 (2) | 1008.2 (4) | 994.5 (2) | 1097.3 (3) |
Z | 2 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.14 | 0.13 | 0.33 | 0.12 |
Crystal size (mm) | 0.30 × 0.30 × 0.10 | 0.29 × 0.21 × 0.20 | 0.25 × 0.12 × 0.10 | 0.30 × 0.25 × 0.15 |
Data collection | ||||
Diffractometer | Stoe IPDS II two-circle | Stoe IPDS II two-circle | Stoe IPDS II two-circle | Stoe IPDS II two-circle |
Absorption correction | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) |
Tmin, Tmax | 0.221, 1.000 | 0.415, 1.000 | 0.565, 1.000 | 0.317, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2369, 1091, 807 | 8325, 1955, 1180 | 7444, 1900, 1443 | 8148, 2119, 1328 |
Rint | 0.046 | 0.132 | 0.074 | 0.065 |
(sin θ/λ)max (Å−1) | 0.613 | 0.620 | 0.613 | 0.615 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.145, 1.05 | 0.064, 0.165, 1.00 | 0.046, 0.105, 1.06 | 0.060, 0.150, 0.99 |
No. of reflections | 1091 | 1955 | 1900 | 2119 |
No. of parameters | 100 | 156 | 147 | 185 |
No. of restraints | 3 | 3 | 3 | 131 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.30 | 0.22, −0.24 | 0.25, −0.44 | 0.17, −0.25 |
(V) | (VI) | (VII) | (VIII) | |
Crystal data | ||||
Chemical formula | C5H4N2O3S·C3H7NO | C5H4N2O3S·C2H6OS | C5H4N2O3S·1.5C4H8O2 | C5H4N2O3S |
Mr | 245.26 | 250.29 | 304.32 | 172.16 |
Crystal system, space group | Monoclinic, P21/c | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 173 | 173 | 173 | 173 |
a, b, c (Å) | 10.1742 (10), 11.4616 (12), 9.9715 (11) | 7.0475 (9), 8.9534 (12), 9.2802 (13) | 5.2819 (7), 10.3542 (12), 13.0071 (15) | 11.409 (3), 15.552 (3), 7.369 (2) |
α, β, γ (°) | 90, 104.318 (8), 90 | 115.79 (1), 95.753 (11), 95.791 (10) | 89.377 (10), 85.143 (10), 77.70 (1) | 90, 97.599 (19), 90 |
V (Å3) | 1126.7 (2) | 517.72 (13) | 692.51 (15) | 1296.0 (6) |
Z | 4 | 2 | 2 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.29 | 0.51 | 0.26 | 0.45 |
Crystal size (mm) | 0.40 × 0.30 × 0.30 | 0.30 × 0.25 × 0.15 | 0.30 × 0.21 × 0.16 | 0.25 × 0.11 × 0.08 |
Data collection | ||||
Diffractometer | Stoe IPDS II two-circle | Stoe IPDS II two-circle | Stoe IPDS II two-circle | Stoe IPDS II two-circle |
Absorption correction | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) |
Tmin, Tmax | 0.499, 1.000 | 0.746, 1.000 | 0.528, 1.000 | 0.149, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8433, 2163, 1796 | 4538, 1976, 1703 | 5885, 2645, 2272 | 9985, 2492, 1294 |
Rint | 0.045 | 0.033 | 0.045 | 0.149 |
(sin θ/λ)max (Å−1) | 0.613 | 0.613 | 0.613 | 0.618 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.093, 1.08 | 0.027, 0.070, 1.05 | 0.036, 0.100, 1.04 | 0.077, 0.164, 0.96 |
No. of reflections | 2163 | 1976 | 2645 | 2492 |
No. of parameters | 157 | 147 | 190 | 217 |
No. of restraints | 3 | 3 | 3 | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.20 | 0.40, −0.23 | 0.30, −0.22 | 0.61, −0.32 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21Ai | 0.872 (17) | 1.940 (18) | 2.804 (3) | 171 (3) |
N3A—H3A···O41Aii | 0.899 (17) | 1.920 (18) | 2.817 (3) | 176 (3) |
O51A—H51C···O21Aiii | 0.84 (4) | 1.97 (4) | 2.741 (3) | 151 (3) |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+1, −z+1; (iii) x+1, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21X | 0.902 (18) | 1.813 (19) | 2.712 (3) | 174 (3) |
N3A—H3A···O51Ai | 0.882 (18) | 2.022 (19) | 2.902 (3) | 176 (4) |
O52A—H52A···O41A | 0.859 (19) | 1.78 (2) | 2.590 (3) | 158 (4) |
C6A—H6A···O41Aii | 0.95 | 2.19 | 3.061 (3) | 151.0 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O52A—H52A···O41A | 0.847 (18) | 1.76 (2) | 2.579 (3) | 162 (3) |
N1A—H1A···O11X | 0.867 (17) | 1.881 (18) | 2.747 (3) | 176 (3) |
N3A—H3A···O11Xi | 0.867 (17) | 1.852 (18) | 2.718 (3) | 177 (3) |
C6A—H6A···O41Aii | 0.95 | 2.54 | 3.422 (3) | 154.2 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O21X | 0.888 (18) | 1.793 (19) | 2.672 (3) | 170 (3) |
O52A—H52A···O41A | 0.873 (18) | 1.77 (2) | 2.605 (3) | 158 (3) |
N3A—H3A···O21Ai | 0.873 (18) | 1.984 (19) | 2.851 (3) | 172 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O51Ai | 0.872 (16) | 1.922 (16) | 2.7846 (19) | 169 (2) |
N3A—H3A···O21X | 0.881 (16) | 1.842 (16) | 2.723 (2) | 179 (2) |
O52A—H52A···O41A | 0.819 (16) | 1.791 (17) | 2.5735 (18) | 159 (2) |
C6A—H6A···O52Ai | 0.95 | 2.53 | 3.269 (2) | 134.7 |
Symmetry code: (i) −x, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O11X | 0.883 (15) | 1.829 (15) | 2.7087 (17) | 174.1 (19) |
N3A—H3A···O11Xi | 0.886 (15) | 1.915 (15) | 2.7983 (18) | 175.2 (19) |
O52A—H52A···O41A | 0.825 (16) | 1.804 (18) | 2.5738 (19) | 155 (2) |
Symmetry code: (i) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6A—H6A···O51Ai | 0.95 | 2.26 | 3.1892 (18) | 165.9 |
N1A—H1A···O1Z | 0.862 (15) | 1.905 (15) | 2.7670 (17) | 177.6 (19) |
N3A—H3A···O1X | 0.898 (14) | 1.894 (15) | 2.7889 (17) | 174.3 (18) |
O52A—H52A···O41A | 0.821 (16) | 1.814 (17) | 2.5998 (16) | 160 (2) |
Symmetry code: (i) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O52Bi | 0.88 (2) | 2.38 (3) | 3.239 (7) | 168 (6) |
N1B—H1B···O52Aii | 0.87 (2) | 2.41 (3) | 3.235 (7) | 158 (6) |
N3A—H3A···S21B | 0.87 (2) | 2.52 (2) | 3.393 (6) | 177 (6) |
N3B—H3B···S21A | 0.87 (2) | 2.57 (3) | 3.409 (6) | 163 (6) |
O52A—H52A···O51Biii | 0.84 (2) | 1.82 (3) | 2.639 (6) | 165 (8) |
O52B—H52B···O51Aiv | 0.85 (2) | 1.81 (2) | 2.657 (6) | 177 (8) |
N1A—H1A···O41Bi | 0.88 (2) | 2.32 (6) | 2.840 (7) | 118 (5) |
C6A—H6A···O41Bi | 0.95 | 2.32 | 2.898 (8) | 118.2 |
N1B—H1B···O41Aii | 0.87 (2) | 2.27 (6) | 2.822 (7) | 121 (6) |
C6B—H6B···O41Aii | 0.95 | 2.33 | 2.891 (8) | 117.4 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y−1/2, −z−1/2; (iii) x, y+1, z; (iv) x, y−1, z. |