Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615015119/sk3598sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615015119/sk3598Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615015119/sk3598IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615015119/sk3598IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615015119/sk3598IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615015119/sk3598Vsup6.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615015119/sk3598Isup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615015119/sk3598IIsup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615015119/sk3598IIIsup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615015119/sk3598IVsup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615015119/sk3598Vsup11.cml |
CCDC references: 1418579; 1418578; 1418577; 1418576; 1418575
As part of our ongoing research, we are interested in the crystal structures of 2,6-dichloroaniline (DCA) and 2,6-dichlorophenol (DCP), and in the interactions of these two compounds in their respective crystal structures. Both compounds contain, aside from their hydrogen -ond donor (–OH and –NH2,respectively), two Cl atoms which can either interact as hydrogen/halogen-bond acceptors, or as halogen-bond donors. Dichlorophenol and its derivatives are widely known as pollutants and their cytotoxic nature towards freshwater, marine algae and animal cells and tissues has been examined previously (Wang et al., 2010). Regardless of this, dichlorophenol derivatives are used as building blocks that can be found in pharmaceuticals and formerly deployed herbicides i.e. Triclosan (McMurry et al., 1998) and Chlometoxyfen (Hikawa, 1984) and also in chemical synthesis (Bourguignon et al., 1993). 2,6-Dichlorophenol, especially, had been used for the characterization of Mitsunobu-type intermediates (Kumara Swamy et al., 2006). In comparison with the dichlorophenol derivatives, chlorophenols are widely used as fungicides, herbicides and insecticides (Zhang et al., 2010). 2,6-Dichloroaniline, however, which is also identified to be toxic to fish, crustaceans and mammals, shows the least toxic properties in comparison with its structural isomers (Valentovic et al., 1995). Similar to their dichloro derivatives, chloroaniline and chlorophenol derivatives can be found as structural components in herbicides and pharmaceuticals, i.e. Linuron (Katsumata et al., 2005), Buturon (Lin et al., 2003), Metosulam (Laganà et al., 2002) and Vancomycin (Loll, 2001). For our research, we decided to cocrystallize the 2,6-dichloro derivatives of aniline and phenol with 2,4-diamino-6-methyl-1,3,5-triazine (DMT) and 6-aminoisocytosine (AIC). Both coformers display strong abilities to form hydrogen bonds (Gerhardt et al., 2011). Moreover, they have a tendency to form certain synthons, precisely synthon 2 and 3s for DMT and both types of synthon 3 for AIC (Gerhardt & Egert, 2015) (Fig. 1). In contrast to their coformers, DCP and DCA are capable to form synthon 2, solely. Thus, they usually form only one- or two-dimensional networks.
Integrating DCP or DCA into the synthon-based networks of DMT or AIC might stabilize, or even expand, the usual packing motifs of DCP and DCA to two- or three-dimensional arrangements. However, the latter probably suggests that the Cl atoms participate in the packing and also implies a noncoplanar arrangement of the dichloro derivatives with their coformers. In order to investigate this issue, cocrystallization attempts of DCP with DMT, and DCA with AIC have been performed.
Unfortunately, only two cocrystals of DCP and DCA were obtained. Three of the obtained crystals contain only DMT or ACI. Nevertheless, it is interesting to investigate the intermolecular interactions and the packing motifs of these structures. The structures studied are 2,4-diamino-6-methyl-1,3,5-triazine–N,N-dimethylacetamide (DMT–DMAC) (1/1), (I), 2,4-diamino-6-methyl-1,3,5-triazine–N-methylpyrrolidin-2-one (DMT–NMP) (1/1), (II), 2,4-diamino-6-methyl-1,3,5-triazine–2,6-dichlorophenol (DMT–DCP) (1/1), (III), 6-aminoisocytosine–N-methylpyrrolidin-2-one (AIC–NMP) (1/1), (IV), and 6-aminoisocytosine–2,6-dichloroaniline–N,N-dimethylacetamide (AIC–DCA–DMAC) (1/1/1), (V).
All experiments have been performed with commercially available substances in various hydrous solvents and at different temperatures. Isothermal solvent evaporation experiments of 3-methyl-6-chlorouracil (M6CU), C5H5ClN2O2, with 2,4-diamino-6-methyl-1,3,5-triazine (DMT), C4H7N5, in N,N-dimethylacetamide, C4H9NO, (DMAC), and N-methylpyrrolidin-2-one C5H9NO, (NMP), each at 50 °C, yielded the two DMT and solvent containing crystals (I) and (II). (III) was obtained during crystallization attempts of DMT with 2,6-dichlorophenole (DCP), C6H4Cl2O, in a mixture of methanol and DMSO (dimethyl sulfoxide) at room temperature. The NMP solvate of 6-aminoisocytosine, (IV), C4H6N4O, (AIC), had been crystallized via isothermal solvent evaporation experiments at room temperature with 2-amino-4-chloro-6-methylpyrimidine. The cocrystal-mono-solvate of AIC with 2,6-dichloroaniline, (V), was also crystallized at room temperature. A detailed summary of the performed isothermal solvent evaporation experiments is presented in Table 1.
Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were initially located by difference Fourier synthesis. Subsequently, H atoms bonded to C atoms were 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 Uiso(H) = 1.5Ueq (C) for methyl H atoms or 1.2Ueq (C) for secondary and aromatic H atoms. H atoms bonded to N and O atoms were refined isotropically, with Uiso(H) = 1.2Ueq(N) for (I), (III) and (V), and 1.5Ueq (O) in (III). For the methyl groups in (II) and (III), free rotation about their local threefold axis was allowed. Distance restraints for the solvent molecules were applied to the 1,2 and 1,3 distances in (IV) and (V). Furthermore, in (IV) and (V), the solvent molecules X are disordered across a pseudo-mirror plane, which passes through atoms O2X and C5X with major site-occupation factors of 0.591 (10) in (IV) and 0.635 (9) in (V). Additionally, in (IV), an isotropic extinction parameter has been refined.
Due to the absence of anomalous scatterers in (I) and in (II), 959 Friedel pairs for (I) and 968 Friedel pairs for (II) were merged before refinement and the absolute structure was not determined.
For the CSD, searches only organic structures with determined three-dimensional coordinates have been analyzed and doubled entries, as well as disordered structures of DCA and DCP derivatives, have been omitted.
The DMAC solvate of DMT, (I), crystallizes in the orthorhombic space group Fdd2 with one planar molecule of DMT and one planar DMAC molecule (r.m.s. deviations for non-H atoms = 0.031 Å for DMT and 0.026 Å for DMAC) within the asymmetric unit (Fig. 2). Both molecules are linked by an N—H···O hydrogen bond, and a dihedral angle of 39.95 (12)° is observed between the planes of the DMT and DMAC molecules. In the packing, synthon 2iN·N connects DMT molecules into chains parallel to [101] and to [101] (Fig. 3 and Table 3). The chains are oriented with an angle of about 35° with respect to each other, resulting in a three-dimensional network (Fig. 4). Furthermore, the NMP molecules fill the empty spaces between the DMT molecules to which they are connected via an N—H···O hydrogen bond (Fig. 3 and Table 3).
An NMP solvate of DMT, (II), shows similar cell parameters and similar hydrogen-bonding patterns as (I). It also crystallizes in the Fdd2 space group and has one planar molecule each of DMT and NMP (r.m.s. deviations for non-H atoms = 0.009 Å for DMT and 0.050 Å for DMAC), which are linked via one N—H···O hydrogen bond (Fig. 5). Synthon 2iN·N chains parallel to [101] and to [101] are arranged at an angle of about 35° with respect to each other (Fig. 6 and Table 4). The NMP solvent molecules make a dihedral angle of 42.15 (7) ° with the DMT molecules to which they are hydrogen bonded. As in (I), a three-dimensional network is observed (Fig. 7).
Solvent evaporation experiments of DMT with DCP in a methanol/dimethyl sulfoxide (DMSO) mixture yielded the solvent-free cocrystal, denoted (III). The asymmetric unit of the triclinic cell contains one planar DMT molecule (r.m.s. deviation for non-H atoms = 0.028 Å) and one planar DCP molecule (r.m.s. deviation for non-H atoms = 0.008 Å), which enclose a dihedral angle of 88.76 (3)° with respect to each other (Fig. 8). As in (I) and (II), DMT molecules form synthon 2iN·N chains running parallel to [110]. The plane of the DMT molecules is parallel to (112), whereas the plane of the DCP molecules is parallel to (243), with a dihedral angle of about 85° between these planes. One DCP molecule connects two adjacent chains via N—H···O and O—H···N hydrogen bonds, resulting in two-dimensional sheets parallel to (001) (Fig. 9 and Table 5).
Cocrystal (IV) features one molecule of 6-aminoisocytosine (AIC) and one disordered NMP molecule within the asymmetric unit (Fig. 10). Both molecules are connected via one N—H···O hydrogen bond and are almost planar, whereby the molecular planes are inclined by an angle of 13.19 (16) ° with respect to each other (r.m.s. deviation for non-H atoms = 0.013 Å for AIC and 0.055 Å for NMP). In the packing, AIC molecules are connected according to synthon 3u via two N—H···N interactions and one N—H···O interaction, forming undulated layers parallel to (001) (Fig. 11 and Table 6). The solvent molecules are located above and below these layers and are connected to the AIC molecules via N—H···O hydrogen bonds (Fig. 12).
Crystallization attempts of DCA with AIC yielded a cocrystal of these two compounds as a DMAC solvate, denoted (V). The asymmetric unit contains one molecule of 2,6-dichloroaniline, A, one disordered DMAC molecule, X, and one molecule of AIC, B (Fig. 13). Each molecule is planar. The AIC molecules are oriented at an angle of 39.13 (5) ° with respect to the DCA molecules (r.m.s. deviation for non-H atoms = 0.018 Å for A, 0.014 Å for B and 0.019 Å for X). N—H···O interactions connect molecules A with B, and B with X, which is inclined by 23.58 (5) ° in relation to B. Similar to (IV), molecules of AIC form synthon 3u-based undulated layers which run parallel to (001) (Fig. 14 and Table 7). An R34(12) hydrogen-bonding pattern (Bernstein et al., 1995), consisting of three N—H···O and one N—H···N interaction by two molecules of B with one molecule each of A and DMAC stabilizes the two-dimensional arrangement in the packing (Fig. 15). The DMAC and DCA molecules are located above and below these layers and are connected to the AIC molecules by N—H···O hydrogen bonds.
A Cambridge Structural Database (CSD, Version 5.36 of November 2014, plus two updates; Groom & Allen, 2014) search was performed for DCP and DCA. The independent hits (16 for DCP and 15 for DCA) are one solvent-free structure for each of DCP and DCA [DCP: CSD refcode DCLPHL (Bavoux & Michel, 1974); DCA: WEMDEX (Dou et al., 1993)], one chlorine salt of I [DCP?] (XEGTOT; Swarmy et al., 2006), a cocrystal of II [DCA?] (NEPXEN; Venter et al., 2013), and 14 (for DCP) or 13 (for DCA) C4-substituted derivatives.
For DCP, ten structures are neutral, of which three crystals display a three-dimensional network [CAKYOE (Varughese et al., 2010), GAKVAP (McKinney & Singh, 1988) and SILGOK (González Martínez & Bernès, 2007)]. In CAKYOE, a C—H···Cl hydrogen bond supports the three-dimensional network, while O—H···Cl and weak Cl···Cl interactions are present in SILGOK. In GAKVAP, a weak Cl···Cl interaction connects two-dimensional chains into a three-dimensional network. Two-dimensional networks are observed in ITEKOH (Kai et al., 2002) and TIJVEN (Eriksson & Eriksson, 2001), wherein no halogen interactions are present in the former case, while weak C—H···Cl hydrogen bonds are found in the latter case. One-dimensional chains and ribbons in five structures [LADTUF (Yang et al., 1993), WOMGUB (Desiraju & Bhatt, 2008), and XAZVUQ, XAZWAX and XAZWEB (Britton, 2006)] are mainly built by O—H···O and O—H···N interactions, but are also stabilized by weak Cl···O and Cl···π interactions. Three of the four ionic crystals are three-dimensional [OBEHOS (Habata et al., 1999), SAQJOJ (Szafran et al., 1997) and XOSGET (Szafran et al., 2015)], whereas the fourth ionic crystal (XAMTOV; Dega-Szafran et al., 2005) shows a one-dimensional arrangement of chains within the packing.
Similar to DCP, ten structures retrieved from the CSD for DCA are neutral. In contrast, no one-dimensional network is observed, while six three-dimensional and four two-dimensional packing arrangements are present. Except for one (ZOBCOI; Simonov et al., 1995), all the three-dimensional crystal structures reveal an involvement of Cl atoms in N—H···Cl hydrogen bonds [FIWGOI (Arun Prasad et al., 2005), TCANIL02 (Gowda et al., 2007) and VABFAH (Qin et al., 2010)], weak C—H···Cl interactions (JEQPAX; Soural et al., 2006) or weak Cl···O interactions (ZOBCIC; Simonov et al., 1992). Opposite to this trend, the two-dimensional networks contain no chlorine interactions [EVICES (Liu et al., 2011), KOGSEE (Dvorkin et al., 1991) and KOGSEF (Simonov et al., 1992)], except for UNUQOK (Wang, 2011), wherein a weak C—H···Cl hydrogen bond is found. Three ionic crystals have been examined. Each includes ionic chlorine, which participates in either a three-dimensional (ACBUET; Carpy et al., 1980) or a two-dimensional network within the packing [SAZRUH (Roschenthaler et al., 2005) and SAZSAO (Roschenthaler et al., 2005)].
Taking a closer look at the two solvent-free crystals, as well as at the cocrystal of DCA and the salt of DCP, one two-dimensional and one three-dimensional arrangement is present in the crystals of DCA. In NEPXEN, chains running along the c maxis are connected via weak C—H···O hydrogen bonds and weak Cl···Cl interactions, forming a two-dimensional pattern, while in WEMDEX, a three-dimensional network is built by a mixture of weak Cl···Cl , C—H···Cl and N—H···N interactions. The solvent-free structure of DCP (DCLPHL) also shows a three-dimensional network, that is mainly built by weak Cl···Cl halogen contacts and O—H···O hydogen bonds. In contrast to the chloride salt of DCA, a three-dimensional pattern is observed for the salt of DCP (XEGTOT), showing O—H···Cl and N—H···Cl hydrogen bonds with the chloride ions.
Comparing the results of the crystallization experiments and the CSD search, no obvious trend including both, i.e. DCP and DCA, can be determined. Both molecules prefer noncoplanar arrangements in cocrystals regarding their coformers and usually show strong hydrogen bonds. Nevertheless, it can be assumed that for neutral cocrystals, two-dimensional networks might be slightly preferred as well as for the CSD search of DCA. In contrast to the solvent-free structures of DCP and DCA, three-dimensional arrangements are slightly favoured and only for DCP derivatives are one-dimensional arrangements present. Both types of molecules differ within their preferred one- or two-dimensional patterns. For DCP, only one H atom interacts as a strong hydrogen-bond donor and, as a consequence of this limitation, one-dimensional networks are predominantly formed. Interestingly, the crystal packing of (III) is mainly a result of strong interactions of almost orthogonal molecules of DCP with respect to DMT, resulting in the two-dimensional arrangement. Otherwise, in (V), the packing is built only by AIC molecules, and DCA molecules are adjusted [attached] to both sides of the layers.
In summary, noncoplanar arrangements of DCP and DCA with respect to their coformers are favoured, which is in agreement with the frequent occurance of structural analogues in pharmacology and biology. Additionally, the integration of DCP and DCA into synthon-based networks enhances their ability to form two-dimensional networks, either strongly involved or just as stabilizing compounds.
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: SHELXL (Sheldrick, 2008) for (I); SHELXL97 (Sheldrick, 2008) for (II), (III), (IV), (V). For all compounds, molecular graphics: Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
C4H7N5·C4H9NO | F(000) = 1824 |
Mr = 212.27 | Dx = 1.267 Mg m−3 |
Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2d | Cell parameters from 8606 reflections |
a = 23.198 (3) Å | θ = 3.5–25.8° |
b = 26.327 (3) Å | µ = 0.09 mm−1 |
c = 7.288 (1) Å | T = 173 K |
V = 4451.0 (10) Å3 | Needle, colourless |
Z = 16 | 0.14 × 0.12 × 0.08 mm |
Stoe IPDS II two-circle diffractometer | 1139 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 996 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.109 |
ω scans | θmax = 25.6°, θmin = 3.5° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −28→28 |
Tmin = 0.884, Tmax = 0.922 | k = −31→31 |
17579 measured reflections | l = −8→8 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.159 | w = 1/[σ2(Fo2) + (0.0846P)2 + 6.4135P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max < 0.001 |
1139 reflections | Δρmax = 0.24 e Å−3 |
148 parameters | Δρmin = −0.28 e Å−3 |
5 restraints | Absolute structure: - |
Primary atom site location: structure-invariant direct methods |
C4H7N5·C4H9NO | V = 4451.0 (10) Å3 |
Mr = 212.27 | Z = 16 |
Orthorhombic, Fdd2 | Mo Kα radiation |
a = 23.198 (3) Å | µ = 0.09 mm−1 |
b = 26.327 (3) Å | T = 173 K |
c = 7.288 (1) Å | 0.14 × 0.12 × 0.08 mm |
Stoe IPDS II two-circle diffractometer | 1139 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 996 reflections with I > 2σ(I) |
Tmin = 0.884, Tmax = 0.922 | Rint = 0.109 |
17579 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 5 restraints |
wR(F2) = 0.159 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.14 | Δρmax = 0.24 e Å−3 |
1139 reflections | Δρmin = −0.28 e Å−3 |
148 parameters | Absolute structure: - |
Experimental. ; |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.50038 (16) | 0.36665 (13) | 0.5231 (5) | 0.0230 (9) | |
C2 | 0.50245 (19) | 0.41755 (16) | 0.5102 (6) | 0.0204 (9) | |
N2 | 0.45481 (15) | 0.44296 (14) | 0.5518 (6) | 0.0247 (9) | |
H21 | 0.4229 (15) | 0.4268 (17) | 0.584 (7) | 0.030* | |
H22 | 0.451 (2) | 0.4764 (10) | 0.539 (7) | 0.030* | |
N3 | 0.54958 (16) | 0.44451 (13) | 0.4587 (6) | 0.0229 (8) | |
C4 | 0.59571 (18) | 0.41644 (16) | 0.4191 (6) | 0.0204 (10) | |
N4 | 0.64339 (16) | 0.44023 (15) | 0.3637 (6) | 0.0285 (10) | |
H41 | 0.6757 (15) | 0.4232 (18) | 0.346 (8) | 0.034* | |
H42 | 0.642 (2) | 0.4728 (11) | 0.332 (8) | 0.034* | |
N5 | 0.59932 (17) | 0.36526 (14) | 0.4306 (6) | 0.0258 (9) | |
C6 | 0.5497 (2) | 0.34317 (15) | 0.4814 (7) | 0.0230 (9) | |
C61 | 0.5499 (2) | 0.28668 (17) | 0.4904 (10) | 0.0388 (13) | |
H61A | 0.5882 | 0.2740 | 0.4571 | 0.058* | |
H61B | 0.5212 | 0.2731 | 0.4047 | 0.058* | |
H61C | 0.5404 | 0.2758 | 0.6154 | 0.058* | |
C1X | 0.5649 (3) | 0.5457 (3) | 0.0886 (10) | 0.0545 (17) | |
H1X1 | 0.5400 | 0.5731 | 0.0440 | 0.082* | |
H1X2 | 0.5452 | 0.5272 | 0.1870 | 0.082* | |
H1X3 | 0.5735 | 0.5223 | −0.0124 | 0.082* | |
C2X | 0.6213 (3) | 0.5683 (2) | 0.1627 (8) | 0.0471 (15) | |
O2X | 0.65926 (18) | 0.54120 (14) | 0.2260 (7) | 0.0509 (11) | |
N3X | 0.6268 (3) | 0.6178 (2) | 0.1502 (8) | 0.0600 (16) | |
C4X | 0.6817 (4) | 0.6403 (3) | 0.2137 (11) | 0.075 (2) | |
H4X1 | 0.6805 | 0.6772 | 0.1973 | 0.112* | |
H4X2 | 0.7137 | 0.6262 | 0.1421 | 0.112* | |
H4X3 | 0.6874 | 0.6323 | 0.3439 | 0.112* | |
C5X | 0.5813 (4) | 0.6515 (3) | 0.0847 (14) | 0.092 (3) | |
H5X1 | 0.5951 | 0.6867 | 0.0872 | 0.138* | |
H5X2 | 0.5474 | 0.6482 | 0.1640 | 0.138* | |
H5X3 | 0.5709 | 0.6422 | −0.0413 | 0.138* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0193 (17) | 0.0193 (17) | 0.031 (2) | −0.0009 (15) | 0.0003 (16) | 0.0028 (17) |
C2 | 0.019 (2) | 0.021 (2) | 0.021 (2) | −0.0024 (18) | −0.0004 (18) | 0.0011 (19) |
N2 | 0.0166 (19) | 0.0161 (17) | 0.042 (2) | 0.0027 (16) | 0.0080 (18) | 0.0042 (18) |
N3 | 0.0185 (16) | 0.0186 (17) | 0.032 (2) | −0.0002 (16) | 0.0032 (15) | 0.0046 (18) |
C4 | 0.015 (2) | 0.018 (2) | 0.028 (2) | −0.0005 (17) | −0.0015 (19) | −0.0011 (19) |
N4 | 0.0182 (19) | 0.0193 (18) | 0.048 (3) | 0.0029 (16) | 0.0025 (19) | 0.0050 (18) |
N5 | 0.0217 (19) | 0.0187 (19) | 0.037 (2) | 0.0019 (15) | 0.0018 (18) | 0.0018 (18) |
C6 | 0.022 (2) | 0.023 (2) | 0.024 (2) | 0.0007 (19) | −0.0029 (18) | 0.007 (2) |
C61 | 0.026 (2) | 0.021 (2) | 0.070 (4) | −0.003 (2) | 0.010 (3) | −0.002 (3) |
C1X | 0.062 (4) | 0.045 (3) | 0.056 (4) | 0.000 (3) | −0.002 (3) | 0.004 (3) |
C2X | 0.068 (4) | 0.038 (3) | 0.035 (3) | 0.003 (3) | 0.017 (3) | 0.006 (3) |
O2X | 0.056 (3) | 0.036 (2) | 0.061 (3) | 0.0007 (19) | 0.001 (2) | 0.018 (2) |
N3X | 0.092 (4) | 0.038 (3) | 0.050 (4) | 0.006 (3) | 0.015 (3) | 0.013 (3) |
C4X | 0.121 (7) | 0.050 (4) | 0.053 (4) | −0.032 (4) | 0.018 (5) | −0.007 (4) |
C5X | 0.129 (8) | 0.062 (5) | 0.086 (6) | 0.046 (5) | 0.036 (6) | 0.038 (5) |
N1—C6 | 1.335 (6) | C61—H61C | 0.9800 |
N1—C2 | 1.344 (6) | C1X—C2X | 1.536 (9) |
C2—N2 | 1.327 (6) | C1X—H1X1 | 0.9800 |
C2—N3 | 1.356 (6) | C1X—H1X2 | 0.9800 |
N2—H21 | 0.89 (2) | C1X—H1X3 | 0.9800 |
N2—H22 | 0.89 (2) | C2X—O2X | 1.224 (7) |
N3—C4 | 1.332 (5) | C2X—N3X | 1.311 (8) |
C4—N4 | 1.334 (6) | N3X—C5X | 1.459 (9) |
C4—N5 | 1.352 (6) | N3X—C4X | 1.479 (9) |
N4—H41 | 0.88 (2) | C4X—H4X1 | 0.9800 |
N4—H42 | 0.89 (2) | C4X—H4X2 | 0.9800 |
N5—C6 | 1.342 (6) | C4X—H4X3 | 0.9800 |
C6—C61 | 1.489 (6) | C5X—H5X1 | 0.9800 |
C61—H61A | 0.9800 | C5X—H5X2 | 0.9800 |
C61—H61B | 0.9800 | C5X—H5X3 | 0.9800 |
C6—N1—C2 | 114.5 (4) | C2X—C1X—H1X1 | 109.5 |
N2—C2—N1 | 117.2 (4) | C2X—C1X—H1X2 | 109.5 |
N2—C2—N3 | 118.1 (4) | H1X1—C1X—H1X2 | 109.5 |
N1—C2—N3 | 124.7 (4) | C2X—C1X—H1X3 | 109.5 |
C2—N2—H21 | 121 (3) | H1X1—C1X—H1X3 | 109.5 |
C2—N2—H22 | 124 (3) | H1X2—C1X—H1X3 | 109.5 |
H21—N2—H22 | 115 (5) | O2X—C2X—N3X | 122.4 (6) |
C4—N3—C2 | 114.6 (3) | O2X—C2X—C1X | 121.3 (5) |
N3—C4—N4 | 118.1 (4) | N3X—C2X—C1X | 116.3 (6) |
N3—C4—N5 | 126.1 (4) | C2X—N3X—C5X | 123.8 (7) |
N4—C4—N5 | 115.8 (4) | C2X—N3X—C4X | 117.4 (6) |
C4—N4—H41 | 121 (4) | C5X—N3X—C4X | 118.8 (7) |
C4—N4—H42 | 120 (3) | N3X—C4X—H4X1 | 109.5 |
H41—N4—H42 | 119 (5) | N3X—C4X—H4X2 | 109.5 |
C6—N5—C4 | 113.3 (4) | H4X1—C4X—H4X2 | 109.5 |
N1—C6—N5 | 126.7 (4) | N3X—C4X—H4X3 | 109.5 |
N1—C6—C61 | 117.1 (4) | H4X1—C4X—H4X3 | 109.5 |
N5—C6—C61 | 116.3 (4) | H4X2—C4X—H4X3 | 109.5 |
C6—C61—H61A | 109.5 | N3X—C5X—H5X1 | 109.5 |
C6—C61—H61B | 109.5 | N3X—C5X—H5X2 | 109.5 |
H61A—C61—H61B | 109.5 | H5X1—C5X—H5X2 | 109.5 |
C6—C61—H61C | 109.5 | N3X—C5X—H5X3 | 109.5 |
H61A—C61—H61C | 109.5 | H5X1—C5X—H5X3 | 109.5 |
H61B—C61—H61C | 109.5 | H5X2—C5X—H5X3 | 109.5 |
C6—N1—C2—N2 | −179.4 (4) | C2—N1—C6—N5 | 0.4 (7) |
C6—N1—C2—N3 | 0.4 (7) | C2—N1—C6—C61 | −179.1 (5) |
N2—C2—N3—C4 | −180.0 (4) | C4—N5—C6—N1 | −1.7 (7) |
N1—C2—N3—C4 | 0.3 (7) | C4—N5—C6—C61 | 177.9 (5) |
C2—N3—C4—N4 | 178.6 (4) | O2X—C2X—N3X—C5X | −176.6 (7) |
C2—N3—C4—N5 | −1.8 (7) | C1X—C2X—N3X—C5X | 4.9 (9) |
N3—C4—N5—C6 | 2.4 (7) | O2X—C2X—N3X—C4X | 0.9 (9) |
N4—C4—N5—C6 | −178.0 (4) | C1X—C2X—N3X—C4X | −177.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···N5i | 0.89 (2) | 2.15 (3) | 3.037 (5) | 175 (5) |
N2—H22···N3ii | 0.89 (2) | 2.16 (3) | 3.041 (5) | 169 (5) |
N4—H41···N1iii | 0.88 (2) | 2.10 (3) | 2.973 (5) | 174 (6) |
N4—H42···O2X | 0.89 (2) | 2.00 (3) | 2.865 (5) | 163 (5) |
Symmetry codes: (i) x−1/4, −y+3/4, z+1/4; (ii) −x+1, −y+1, z; (iii) x+1/4, −y+3/4, z−1/4. |
C4H7N5·C5H9NO | F(000) = 1920 |
Mr = 224.28 | Dx = 1.330 Mg m−3 |
Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2d | Cell parameters from 15487 reflections |
a = 23.178 (2) Å | θ = 3.5–26.0° |
b = 26.3327 (17) Å | µ = 0.09 mm−1 |
c = 7.3428 (5) Å | T = 173 K |
V = 4481.7 (6) Å3 | Block, colourless |
Z = 16 | 0.19 × 0.14 × 0.10 mm |
Stoe IPDS II two-circle diffractometer | 1147 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 1050 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.104 |
ω scans | θmax = 25.6°, θmin = 3.5° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −28→28 |
Tmin = 0.623, Tmax = 0.776 | k = −32→31 |
27934 measured reflections | l = −8→8 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0505P)2 + 1.9967P] where P = (Fo2 + 2Fc2)/3 |
S = 1.22 | (Δ/σ)max < 0.001 |
1147 reflections | Δρmax = 0.16 e Å−3 |
159 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: - |
Primary atom site location: structure-invariant direct methods |
C4H7N5·C5H9NO | V = 4481.7 (6) Å3 |
Mr = 224.28 | Z = 16 |
Orthorhombic, Fdd2 | Mo Kα radiation |
a = 23.178 (2) Å | µ = 0.09 mm−1 |
b = 26.3327 (17) Å | T = 173 K |
c = 7.3428 (5) Å | 0.19 × 0.14 × 0.10 mm |
Stoe IPDS II two-circle diffractometer | 1147 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1050 reflections with I > 2σ(I) |
Tmin = 0.623, Tmax = 0.776 | Rint = 0.104 |
27934 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 1 restraint |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.22 | Δρmax = 0.16 e Å−3 |
1147 reflections | Δρmin = −0.20 e Å−3 |
159 parameters | Absolute structure: - |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.49594 (12) | 0.36682 (10) | 0.5730 (4) | 0.0228 (7) | |
C2 | 0.49845 (14) | 0.41812 (12) | 0.5642 (5) | 0.0200 (7) | |
N2 | 0.45130 (13) | 0.44390 (12) | 0.6090 (5) | 0.0249 (7) | |
H21 | 0.4501 (17) | 0.4796 (17) | 0.595 (5) | 0.030* | |
H22 | 0.4216 (18) | 0.4258 (16) | 0.627 (6) | 0.030* | |
N3 | 0.54562 (12) | 0.44473 (10) | 0.5151 (5) | 0.0209 (6) | |
C4 | 0.59207 (14) | 0.41692 (12) | 0.4753 (5) | 0.0199 (8) | |
N4 | 0.63988 (13) | 0.44089 (12) | 0.4230 (5) | 0.0233 (7) | |
H41 | 0.6692 (19) | 0.4242 (16) | 0.388 (6) | 0.028* | |
H42 | 0.6392 (16) | 0.4738 (16) | 0.406 (6) | 0.028* | |
N5 | 0.59445 (12) | 0.36540 (10) | 0.4812 (4) | 0.0224 (7) | |
C6 | 0.54485 (15) | 0.34311 (12) | 0.5305 (6) | 0.0227 (8) | |
C61 | 0.54503 (18) | 0.28666 (13) | 0.5392 (7) | 0.0377 (11) | |
H61A | 0.5523 | 0.2758 | 0.6647 | 0.056* | |
H61B | 0.5754 | 0.2734 | 0.4595 | 0.056* | |
H61C | 0.5075 | 0.2737 | 0.4991 | 0.056* | |
N1X | 0.58914 (12) | 0.58571 (12) | 0.1681 (5) | 0.0305 (8) | |
C1X | 0.55352 (18) | 0.54228 (16) | 0.1290 (7) | 0.0385 (10) | |
H1X1 | 0.5742 | 0.5112 | 0.1623 | 0.058* | |
H1X2 | 0.5444 | 0.5416 | −0.0013 | 0.058* | |
H1X3 | 0.5177 | 0.5445 | 0.1994 | 0.058* | |
C2X | 0.64175 (16) | 0.58309 (15) | 0.2446 (6) | 0.0308 (9) | |
O2X | 0.66470 (12) | 0.54405 (11) | 0.2990 (5) | 0.0427 (8) | |
C3X | 0.66724 (16) | 0.63528 (14) | 0.2470 (6) | 0.0316 (9) | |
H3X1 | 0.7003 | 0.6374 | 0.1621 | 0.038* | |
H3X2 | 0.6808 | 0.6441 | 0.3710 | 0.038* | |
C4X | 0.61915 (17) | 0.67100 (14) | 0.1875 (6) | 0.0333 (9) | |
H4X1 | 0.6330 | 0.6946 | 0.0921 | 0.040* | |
H4X2 | 0.6049 | 0.6911 | 0.2921 | 0.040* | |
C5X | 0.57135 (16) | 0.63644 (14) | 0.1128 (6) | 0.0314 (9) | |
H5X1 | 0.5335 | 0.6453 | 0.1663 | 0.038* | |
H5X2 | 0.5688 | 0.6390 | −0.0215 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0182 (14) | 0.0193 (14) | 0.0308 (18) | 0.0020 (12) | 0.0057 (12) | 0.0016 (14) |
C2 | 0.0174 (15) | 0.0232 (17) | 0.0195 (17) | 0.0006 (14) | −0.0017 (13) | −0.0004 (16) |
N2 | 0.0183 (15) | 0.0167 (15) | 0.0396 (19) | −0.0023 (13) | 0.0052 (15) | 0.0013 (14) |
N3 | 0.0154 (12) | 0.0186 (13) | 0.0288 (15) | −0.0002 (12) | 0.0012 (12) | 0.0015 (14) |
C4 | 0.0150 (15) | 0.0229 (18) | 0.0218 (19) | −0.0003 (14) | −0.0006 (14) | −0.0010 (16) |
N4 | 0.0149 (14) | 0.0161 (14) | 0.0389 (19) | 0.0021 (13) | 0.0058 (14) | 0.0008 (13) |
N5 | 0.0195 (15) | 0.0159 (15) | 0.0319 (18) | 0.0021 (11) | 0.0021 (13) | 0.0009 (14) |
C6 | 0.0202 (15) | 0.0219 (16) | 0.0260 (19) | −0.0002 (15) | −0.0025 (14) | 0.0000 (16) |
C61 | 0.0282 (18) | 0.0218 (18) | 0.063 (3) | 0.0013 (17) | 0.012 (2) | −0.004 (2) |
N1X | 0.0261 (16) | 0.0292 (17) | 0.0362 (19) | −0.0025 (13) | 0.0013 (16) | 0.0057 (15) |
C1X | 0.033 (2) | 0.035 (2) | 0.047 (3) | −0.0059 (18) | 0.002 (2) | −0.002 (2) |
C2X | 0.0286 (19) | 0.033 (2) | 0.031 (2) | 0.0023 (17) | 0.0052 (18) | 0.0052 (18) |
O2X | 0.0350 (15) | 0.0310 (15) | 0.062 (2) | 0.0070 (12) | −0.0020 (14) | 0.0141 (15) |
C3X | 0.030 (2) | 0.033 (2) | 0.031 (2) | −0.0018 (17) | 0.0016 (18) | 0.0044 (18) |
C4X | 0.041 (2) | 0.0260 (19) | 0.033 (2) | 0.0008 (18) | 0.0035 (18) | 0.0027 (17) |
C5X | 0.0297 (19) | 0.032 (2) | 0.033 (2) | 0.0076 (17) | 0.0028 (18) | 0.0079 (18) |
N1—C6 | 1.331 (4) | N1X—C2X | 1.344 (5) |
N1—C2 | 1.354 (4) | N1X—C1X | 1.439 (5) |
C2—N2 | 1.328 (5) | N1X—C5X | 1.456 (5) |
C2—N3 | 1.348 (4) | C1X—H1X1 | 0.9800 |
N2—H21 | 0.95 (4) | C1X—H1X2 | 0.9800 |
N2—H22 | 0.85 (4) | C1X—H1X3 | 0.9800 |
N3—C4 | 1.334 (4) | C2X—O2X | 1.224 (5) |
C4—N4 | 1.332 (4) | C2X—C3X | 1.496 (5) |
C4—N5 | 1.358 (4) | C3X—C4X | 1.522 (5) |
N4—H41 | 0.85 (5) | C3X—H3X1 | 0.9900 |
N4—H42 | 0.88 (4) | C3X—H3X2 | 0.9900 |
N5—C6 | 1.341 (4) | C4X—C5X | 1.535 (6) |
C6—C61 | 1.488 (5) | C4X—H4X1 | 0.9900 |
C61—H61A | 0.9800 | C4X—H4X2 | 0.9900 |
C61—H61B | 0.9800 | C5X—H5X1 | 0.9900 |
C61—H61C | 0.9800 | C5X—H5X2 | 0.9900 |
C6—N1—C2 | 114.8 (3) | N1X—C1X—H1X1 | 109.5 |
N2—C2—N3 | 117.9 (3) | N1X—C1X—H1X2 | 109.5 |
N2—C2—N1 | 117.6 (3) | H1X1—C1X—H1X2 | 109.5 |
N3—C2—N1 | 124.5 (3) | N1X—C1X—H1X3 | 109.5 |
C2—N2—H21 | 120 (2) | H1X1—C1X—H1X3 | 109.5 |
C2—N2—H22 | 115 (3) | H1X2—C1X—H1X3 | 109.5 |
H21—N2—H22 | 124 (4) | O2X—C2X—N1X | 125.0 (4) |
C4—N3—C2 | 115.3 (3) | O2X—C2X—C3X | 126.6 (4) |
N4—C4—N3 | 118.3 (3) | N1X—C2X—C3X | 108.4 (3) |
N4—C4—N5 | 116.7 (3) | C2X—C3X—C4X | 106.0 (3) |
N3—C4—N5 | 125.0 (3) | C2X—C3X—H3X1 | 110.5 |
C4—N4—H41 | 121 (3) | C4X—C3X—H3X1 | 110.5 |
C4—N4—H42 | 120 (3) | C2X—C3X—H3X2 | 110.5 |
H41—N4—H42 | 119 (4) | C4X—C3X—H3X2 | 110.5 |
C6—N5—C4 | 114.2 (3) | H3X1—C3X—H3X2 | 108.7 |
N1—C6—N5 | 126.0 (3) | C3X—C4X—C5X | 105.4 (3) |
N1—C6—C61 | 117.4 (3) | C3X—C4X—H4X1 | 110.7 |
N5—C6—C61 | 116.5 (3) | C5X—C4X—H4X1 | 110.7 |
C6—C61—H61A | 109.5 | C3X—C4X—H4X2 | 110.7 |
C6—C61—H61B | 109.5 | C5X—C4X—H4X2 | 110.7 |
H61A—C61—H61B | 109.5 | H4X1—C4X—H4X2 | 108.8 |
C6—C61—H61C | 109.5 | N1X—C5X—C4X | 103.9 (3) |
H61A—C61—H61C | 109.5 | N1X—C5X—H5X1 | 111.0 |
H61B—C61—H61C | 109.5 | C4X—C5X—H5X1 | 111.0 |
C2X—N1X—C1X | 124.3 (3) | N1X—C5X—H5X2 | 111.0 |
C2X—N1X—C5X | 114.9 (3) | C4X—C5X—H5X2 | 111.0 |
C1X—N1X—C5X | 120.7 (3) | H5X1—C5X—H5X2 | 109.0 |
C6—N1—C2—N2 | −178.6 (4) | C4—N5—C6—C61 | 180.0 (4) |
C6—N1—C2—N3 | 0.7 (6) | C1X—N1X—C2X—O2X | −4.0 (6) |
N2—C2—N3—C4 | 178.6 (3) | C5X—N1X—C2X—O2X | −179.5 (4) |
N1—C2—N3—C4 | −0.6 (6) | C1X—N1X—C2X—C3X | 174.7 (4) |
C2—N3—C4—N4 | 179.0 (3) | C5X—N1X—C2X—C3X | −0.8 (5) |
C2—N3—C4—N5 | 0.0 (6) | O2X—C2X—C3X—C4X | −173.0 (4) |
N4—C4—N5—C6 | −178.5 (3) | N1X—C2X—C3X—C4X | 8.3 (4) |
N3—C4—N5—C6 | 0.4 (5) | C2X—C3X—C4X—C5X | −12.1 (4) |
C2—N1—C6—N5 | −0.1 (6) | C2X—N1X—C5X—C4X | −6.9 (5) |
C2—N1—C6—C61 | 179.5 (4) | C1X—N1X—C5X—C4X | 177.4 (4) |
C4—N5—C6—N1 | −0.4 (6) | C3X—C4X—C5X—N1X | 11.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···N3i | 0.95 (4) | 2.08 (4) | 3.013 (4) | 169 (4) |
N2—H22···N5ii | 0.85 (4) | 2.23 (5) | 3.062 (4) | 168 (4) |
N4—H41···N1iii | 0.85 (5) | 2.14 (5) | 2.982 (4) | 175 (4) |
N4—H42···O2X | 0.88 (4) | 2.09 (4) | 2.922 (4) | 157 (4) |
Symmetry codes: (i) −x+1, −y+1, z; (ii) x−1/4, −y+3/4, z+1/4; (iii) x+1/4, −y+3/4, z−1/4. |
C6H4Cl2O·C4H7N5 | Z = 2 |
Mr = 288.14 | F(000) = 296 |
Triclinic, P1 | Dx = 1.516 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.0318 (7) Å | Cell parameters from 2942 reflections |
b = 8.5779 (11) Å | θ = 3.5–26.0° |
c = 15.008 (2) Å | µ = 0.51 mm−1 |
α = 93.929 (11)° | T = 173 K |
β = 96.214 (11)° | Needle, colourless |
γ = 100.121 (11)° | 0.19 × 0.12 × 0.06 mm |
V = 631.41 (15) Å3 |
Stoe IPDS II two-circle diffractometer | 2354 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 1864 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.033 |
ω scans | θmax = 25.6°, θmin = 3.5° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −6→5 |
Tmin = 0.719, Tmax = 0.872 | k = −10→10 |
5126 measured reflections | l = −18→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0448P)2] where P = (Fo2 + 2Fc2)/3 |
2354 reflections | (Δ/σ)max < 0.001 |
180 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C6H4Cl2O·C4H7N5 | γ = 100.121 (11)° |
Mr = 288.14 | V = 631.41 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.0318 (7) Å | Mo Kα radiation |
b = 8.5779 (11) Å | µ = 0.51 mm−1 |
c = 15.008 (2) Å | T = 173 K |
α = 93.929 (11)° | 0.19 × 0.12 × 0.06 mm |
β = 96.214 (11)° |
Stoe IPDS II two-circle diffractometer | 2354 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1864 reflections with I > 2σ(I) |
Tmin = 0.719, Tmax = 0.872 | Rint = 0.033 |
5126 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.081 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.19 e Å−3 |
2354 reflections | Δρmin = −0.21 e Å−3 |
180 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1B | 0.9771 (3) | 0.16148 (16) | 0.42259 (10) | 0.0264 (3) | |
C2B | 0.8271 (4) | 0.21542 (19) | 0.48369 (12) | 0.0246 (4) | |
N2B | 0.7876 (4) | 0.1316 (2) | 0.55389 (12) | 0.0329 (4) | |
H2B1 | 0.706 (5) | 0.168 (3) | 0.5937 (16) | 0.040* | |
H2B2 | 0.853 (5) | 0.048 (3) | 0.5601 (16) | 0.040* | |
N3B | 0.7150 (3) | 0.34583 (16) | 0.47818 (10) | 0.0248 (3) | |
C4B | 0.7728 (4) | 0.42905 (19) | 0.40828 (11) | 0.0227 (4) | |
N4B | 0.6633 (4) | 0.55767 (19) | 0.39815 (12) | 0.0294 (4) | |
H4B1 | 0.679 (5) | 0.603 (3) | 0.3510 (16) | 0.035* | |
H4B2 | 0.545 (5) | 0.579 (3) | 0.4332 (16) | 0.035* | |
N5B | 0.9340 (3) | 0.39039 (16) | 0.34689 (10) | 0.0256 (3) | |
C6B | 1.0255 (4) | 0.2552 (2) | 0.35688 (12) | 0.0246 (4) | |
C61B | 1.1942 (4) | 0.2055 (2) | 0.28837 (14) | 0.0332 (5) | |
H6B1 | 1.3221 | 0.1434 | 0.3158 | 0.050* | 0.71 (2) |
H6B2 | 1.2956 | 0.3000 | 0.2659 | 0.050* | 0.71 (2) |
H6B3 | 1.0758 | 0.1404 | 0.2383 | 0.050* | 0.71 (2) |
H6BA | 1.3856 | 0.2532 | 0.3069 | 0.050* | 0.29 (2) |
H6BB | 1.1342 | 0.2412 | 0.2302 | 0.050* | 0.29 (2) |
H6BC | 1.1738 | 0.0894 | 0.2829 | 0.050* | 0.29 (2) |
C1A | 0.1526 (4) | 0.6818 (2) | 0.19030 (12) | 0.0261 (4) | |
O1A | 0.1896 (3) | 0.62854 (16) | 0.27128 (9) | 0.0325 (3) | |
H1A | 0.083 (6) | 0.545 (3) | 0.2841 (17) | 0.049* | |
C2A | −0.0606 (4) | 0.6224 (2) | 0.12390 (13) | 0.0326 (4) | |
Cl2A | −0.30587 (12) | 0.46466 (7) | 0.14567 (4) | 0.04572 (17) | |
C3A | −0.0874 (5) | 0.6851 (3) | 0.04147 (15) | 0.0466 (6) | |
H3A | −0.2353 | 0.6409 | −0.0030 | 0.056* | |
C4A | 0.1029 (6) | 0.8121 (3) | 0.02492 (16) | 0.0551 (7) | |
H4A | 0.0858 | 0.8563 | −0.0313 | 0.066* | |
C5A | 0.3175 (6) | 0.8757 (3) | 0.08890 (16) | 0.0473 (6) | |
H5A | 0.4482 | 0.9638 | 0.0773 | 0.057* | |
C6A | 0.3417 (4) | 0.8105 (2) | 0.17021 (13) | 0.0315 (4) | |
Cl6A | 0.61299 (11) | 0.88885 (6) | 0.25170 (4) | 0.04033 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1B | 0.0305 (9) | 0.0197 (7) | 0.0300 (8) | 0.0056 (6) | 0.0067 (7) | 0.0020 (6) |
C2B | 0.0262 (10) | 0.0188 (8) | 0.0280 (9) | 0.0020 (7) | 0.0032 (8) | 0.0016 (7) |
N2B | 0.0466 (12) | 0.0248 (8) | 0.0336 (9) | 0.0150 (8) | 0.0145 (8) | 0.0093 (7) |
N3B | 0.0244 (8) | 0.0221 (7) | 0.0283 (8) | 0.0048 (6) | 0.0038 (6) | 0.0039 (6) |
C4B | 0.0192 (9) | 0.0215 (8) | 0.0257 (9) | 0.0016 (7) | −0.0013 (7) | 0.0026 (7) |
N4B | 0.0314 (10) | 0.0301 (8) | 0.0319 (9) | 0.0131 (7) | 0.0091 (7) | 0.0126 (7) |
N5B | 0.0246 (8) | 0.0243 (8) | 0.0282 (8) | 0.0038 (6) | 0.0049 (6) | 0.0036 (6) |
C6B | 0.0236 (10) | 0.0201 (8) | 0.0284 (9) | 0.0015 (7) | 0.0014 (7) | 0.0004 (7) |
C61B | 0.0354 (12) | 0.0279 (9) | 0.0386 (11) | 0.0066 (8) | 0.0140 (9) | 0.0027 (8) |
C1A | 0.0271 (10) | 0.0267 (9) | 0.0275 (9) | 0.0099 (7) | 0.0065 (8) | 0.0046 (7) |
O1A | 0.0320 (8) | 0.0326 (7) | 0.0295 (7) | −0.0032 (6) | −0.0015 (6) | 0.0107 (6) |
C2A | 0.0330 (11) | 0.0364 (10) | 0.0298 (10) | 0.0095 (8) | 0.0055 (8) | 0.0035 (8) |
Cl2A | 0.0367 (3) | 0.0533 (3) | 0.0395 (3) | −0.0067 (2) | −0.0046 (2) | 0.0029 (2) |
C3A | 0.0510 (15) | 0.0591 (14) | 0.0296 (11) | 0.0143 (11) | −0.0035 (10) | 0.0059 (10) |
C4A | 0.0724 (19) | 0.0630 (15) | 0.0335 (12) | 0.0149 (14) | 0.0078 (12) | 0.0223 (11) |
C5A | 0.0588 (16) | 0.0437 (12) | 0.0433 (13) | 0.0072 (11) | 0.0191 (12) | 0.0179 (10) |
C6A | 0.0316 (11) | 0.0303 (10) | 0.0349 (11) | 0.0080 (8) | 0.0091 (9) | 0.0049 (8) |
Cl6A | 0.0348 (3) | 0.0338 (3) | 0.0491 (3) | −0.0038 (2) | 0.0066 (2) | 0.0050 (2) |
N1B—C6B | 1.330 (2) | C61B—H6BA | 0.9800 |
N1B—C2B | 1.356 (2) | C61B—H6BB | 0.9800 |
C2B—N2B | 1.329 (2) | C61B—H6BC | 0.9800 |
C2B—N3B | 1.342 (2) | C1A—O1A | 1.333 (2) |
N2B—H2B1 | 0.84 (2) | C1A—C2A | 1.382 (3) |
N2B—H2B2 | 0.85 (3) | C1A—C6A | 1.397 (3) |
N3B—C4B | 1.338 (2) | O1A—H1A | 0.86 (3) |
C4B—N4B | 1.328 (2) | C2A—C3A | 1.385 (3) |
C4B—N5B | 1.354 (2) | C2A—Cl2A | 1.738 (2) |
N4B—H4B1 | 0.83 (2) | C3A—C4A | 1.374 (4) |
N4B—H4B2 | 0.87 (3) | C3A—H3A | 0.9500 |
N5B—C6B | 1.332 (2) | C4A—C5A | 1.372 (4) |
C6B—C61B | 1.488 (3) | C4A—H4A | 0.9500 |
C61B—H6B1 | 0.9800 | C5A—C6A | 1.379 (3) |
C61B—H6B2 | 0.9800 | C5A—H5A | 0.9500 |
C61B—H6B3 | 0.9800 | C6A—Cl6A | 1.736 (2) |
C6B—N1B—C2B | 114.68 (15) | H6BA—C61B—H6BB | 109.5 |
N2B—C2B—N3B | 117.89 (17) | C6B—C61B—H6BC | 109.5 |
N2B—C2B—N1B | 117.13 (16) | H6BA—C61B—H6BC | 109.5 |
N3B—C2B—N1B | 124.98 (15) | H6BB—C61B—H6BC | 109.5 |
C2B—N2B—H2B1 | 117.3 (15) | O1A—C1A—C2A | 125.68 (17) |
C2B—N2B—H2B2 | 121.3 (16) | O1A—C1A—C6A | 117.98 (18) |
H2B1—N2B—H2B2 | 121 (2) | C2A—C1A—C6A | 116.34 (17) |
C4B—N3B—C2B | 114.98 (15) | C1A—O1A—H1A | 120.0 (17) |
N4B—C4B—N3B | 117.81 (17) | C1A—C2A—C3A | 122.5 (2) |
N4B—C4B—N5B | 117.79 (16) | C1A—C2A—Cl2A | 118.49 (14) |
N3B—C4B—N5B | 124.40 (16) | C3A—C2A—Cl2A | 119.03 (18) |
C4B—N4B—H4B1 | 118.5 (15) | C4A—C3A—C2A | 119.1 (2) |
C4B—N4B—H4B2 | 119.1 (14) | C4A—C3A—H3A | 120.4 |
H4B1—N4B—H4B2 | 121 (2) | C2A—C3A—H3A | 120.4 |
C6B—N5B—C4B | 115.45 (14) | C5A—C4A—C3A | 120.5 (2) |
N1B—C6B—N5B | 125.32 (17) | C5A—C4A—H4A | 119.7 |
N1B—C6B—C61B | 117.75 (16) | C3A—C4A—H4A | 119.7 |
N5B—C6B—C61B | 116.93 (15) | C4A—C5A—C6A | 119.4 (2) |
C6B—C61B—H6B1 | 109.5 | C4A—C5A—H5A | 120.3 |
C6B—C61B—H6B2 | 109.5 | C6A—C5A—H5A | 120.3 |
C6B—C61B—H6B3 | 109.5 | C5A—C6A—C1A | 122.1 (2) |
C6B—C61B—H6BA | 109.5 | C5A—C6A—Cl6A | 119.97 (17) |
C6B—C61B—H6BB | 109.5 | C1A—C6A—Cl6A | 117.89 (14) |
C6B—N1B—C2B—N2B | −175.78 (18) | C6A—C1A—C2A—C3A | 0.3 (3) |
C6B—N1B—C2B—N3B | 4.6 (3) | O1A—C1A—C2A—Cl2A | 0.1 (3) |
N2B—C2B—N3B—C4B | 177.00 (17) | C6A—C1A—C2A—Cl2A | −178.86 (14) |
N1B—C2B—N3B—C4B | −3.4 (3) | C1A—C2A—C3A—C4A | −0.6 (3) |
C2B—N3B—C4B—N4B | 178.67 (16) | Cl2A—C2A—C3A—C4A | 178.52 (19) |
C2B—N3B—C4B—N5B | −0.9 (3) | C2A—C3A—C4A—C5A | 0.3 (4) |
N4B—C4B—N5B—C6B | −176.09 (17) | C3A—C4A—C5A—C6A | 0.3 (4) |
N3B—C4B—N5B—C6B | 3.5 (3) | C4A—C5A—C6A—C1A | −0.6 (3) |
C2B—N1B—C6B—N5B | −1.7 (3) | C4A—C5A—C6A—Cl6A | 179.68 (19) |
C2B—N1B—C6B—C61B | 178.69 (17) | O1A—C1A—C6A—C5A | −178.74 (19) |
C4B—N5B—C6B—N1B | −2.1 (3) | C2A—C1A—C6A—C5A | 0.3 (3) |
C4B—N5B—C6B—C61B | 177.56 (16) | O1A—C1A—C6A—Cl6A | 1.0 (2) |
O1A—C1A—C2A—C3A | 179.3 (2) | C2A—C1A—C6A—Cl6A | −179.97 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4B—H4B1···O1A | 0.83 (2) | 2.68 (2) | 3.060 (2) | 110 (2) |
N4B—H4B1···Cl6A | 0.83 (2) | 3.01 (2) | 3.7354 (17) | 147 (2) |
N2B—H2B1···O1Ai | 0.84 (2) | 2.53 (2) | 3.200 (2) | 139 (2) |
N2B—H2B2···N1Bii | 0.85 (3) | 2.14 (3) | 2.987 (2) | 179 (2) |
N4B—H4B2···N3Bi | 0.87 (3) | 2.11 (3) | 2.977 (2) | 174 (2) |
O1A—H1A···N5Biii | 0.86 (3) | 1.78 (3) | 2.6123 (19) | 160 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) x−1, y, z. |
C4H6N4O·C5H9NO | F(000) = 480 |
Mr = 225.26 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25481 reflections |
a = 8.1456 (5) Å | θ = 3.3–26.0° |
b = 9.2289 (6) Å | µ = 0.10 mm−1 |
c = 14.9731 (9) Å | T = 173 K |
β = 96.463 (5)° | Block, colourless |
V = 1118.45 (12) Å3 | 0.50 × 0.45 × 0.30 mm |
Z = 4 |
Stoe IPDS II two-circle diffractometer | 2098 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 1912 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.073 |
ω scans | θmax = 25.7°, θmin = 3.4° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −9→9 |
Tmin = 0.869, Tmax = 0.914 | k = −11→11 |
28235 measured reflections | l = −17→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.179 | w = 1/[σ2(Fo2) + (0.0893P)2 + 0.8169P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2098 reflections | Δρmax = 0.61 e Å−3 |
212 parameters | Δρmin = −0.41 e Å−3 |
32 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.022 (7) |
C4H6N4O·C5H9NO | V = 1118.45 (12) Å3 |
Mr = 225.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.1456 (5) Å | µ = 0.10 mm−1 |
b = 9.2289 (6) Å | T = 173 K |
c = 14.9731 (9) Å | 0.50 × 0.45 × 0.30 mm |
β = 96.463 (5)° |
Stoe IPDS II two-circle diffractometer | 2098 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 1912 reflections with I > 2σ(I) |
Tmin = 0.869, Tmax = 0.914 | Rint = 0.073 |
28235 measured reflections |
R[F2 > 2σ(F2)] = 0.065 | 32 restraints |
wR(F2) = 0.179 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.61 e Å−3 |
2098 reflections | Δρmin = −0.41 e Å−3 |
212 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.3959 (2) | 0.33450 (19) | 0.70055 (13) | 0.0351 (5) | |
C2 | 0.4815 (3) | 0.4517 (2) | 0.72640 (15) | 0.0352 (5) | |
N2 | 0.6421 (2) | 0.4574 (2) | 0.71351 (16) | 0.0426 (6) | |
H21 | 0.689 (4) | 0.371 (3) | 0.7025 (19) | 0.048 (7)* | |
H22 | 0.704 (4) | 0.530 (3) | 0.745 (2) | 0.051 (8)* | |
N3 | 0.4148 (2) | 0.5680 (2) | 0.76271 (14) | 0.0360 (5) | |
H3 | 0.479 (4) | 0.646 (4) | 0.7774 (19) | 0.052 (8)* | |
C4 | 0.2487 (3) | 0.5746 (2) | 0.77620 (15) | 0.0347 (5) | |
O4 | 0.19854 (19) | 0.68802 (17) | 0.81076 (12) | 0.0420 (5) | |
C5 | 0.1561 (3) | 0.4521 (2) | 0.74841 (16) | 0.0365 (6) | |
H5 | 0.0416 | 0.4482 | 0.7553 | 0.044* | |
C6 | 0.2316 (3) | 0.3366 (2) | 0.71089 (15) | 0.0337 (5) | |
N6 | 0.1494 (3) | 0.2150 (2) | 0.68309 (16) | 0.0409 (5) | |
H61 | 0.191 (4) | 0.162 (3) | 0.644 (2) | 0.049 (8)* | |
H62 | 0.038 (5) | 0.214 (3) | 0.686 (2) | 0.060 (9)* | |
O2X | 0.2800 (4) | −0.0024 (3) | 0.5758 (2) | 0.1088 (12) | |
C5X | 0.2443 (8) | −0.3733 (4) | 0.5204 (3) | 0.1028 (17) | |
H5X1 | 0.2862 | −0.4544 | 0.5598 | 0.123* | 0.591 (9) |
H5X2 | 0.2510 | −0.3983 | 0.4566 | 0.123* | 0.591 (9) |
H5XA | 0.1878 | −0.3978 | 0.4602 | 0.123* | 0.409 (9) |
H5XB | 0.2311 | −0.4547 | 0.5620 | 0.123* | 0.409 (9) |
N1X | 0.3228 (8) | −0.2372 (5) | 0.5459 (3) | 0.0684 (18) | 0.591 (9) |
C1X | 0.4979 (10) | −0.2377 (10) | 0.5403 (8) | 0.085 (3) | 0.591 (9) |
H1X1 | 0.5350 | −0.3373 | 0.5317 | 0.127* | 0.591 (9) |
H1X2 | 0.5556 | −0.1984 | 0.5960 | 0.127* | 0.591 (9) |
H1X3 | 0.5224 | −0.1779 | 0.4894 | 0.127* | 0.591 (9) |
C2X | 0.2360 (11) | −0.1221 (7) | 0.5557 (9) | 0.063 (3) | 0.591 (9) |
C3X | 0.0540 (8) | −0.1597 (11) | 0.5493 (6) | 0.095 (3) | 0.591 (9) |
H3X1 | 0.0050 | −0.1331 | 0.6046 | 0.114* | 0.591 (9) |
H3X2 | −0.0097 | −0.1138 | 0.4966 | 0.114* | 0.591 (9) |
C4X | 0.0661 (13) | −0.3216 (12) | 0.5385 (10) | 0.142 (6) | 0.591 (9) |
H4X1 | −0.0148 | −0.3529 | 0.4878 | 0.171* | 0.591 (9) |
H4X2 | 0.0363 | −0.3692 | 0.5937 | 0.171* | 0.591 (9) |
N1X' | 0.1840 (11) | −0.2455 (8) | 0.5520 (5) | 0.080 (3) | 0.409 (9) |
C1X' | 0.0141 (14) | −0.2659 (16) | 0.5624 (11) | 0.082 (4) | 0.409 (9) |
H1XA | −0.0177 | −0.3661 | 0.5472 | 0.123* | 0.409 (9) |
H1XB | −0.0531 | −0.1995 | 0.5224 | 0.123* | 0.409 (9) |
H1XC | −0.0041 | −0.2461 | 0.6249 | 0.123* | 0.409 (9) |
C2X' | 0.2852 (17) | −0.1335 (11) | 0.5626 (19) | 0.093 (6) | 0.409 (9) |
C3X' | 0.4550 (19) | −0.1781 (14) | 0.5369 (13) | 0.122 (7) | 0.409 (9) |
H3XA | 0.4828 | −0.1242 | 0.4834 | 0.147* | 0.409 (9) |
H3XB | 0.5428 | −0.1619 | 0.5872 | 0.147* | 0.409 (9) |
C4X' | 0.4317 (13) | −0.3364 (12) | 0.5169 (8) | 0.104 (5) | 0.409 (9) |
H4XA | 0.5014 | −0.3948 | 0.5619 | 0.125* | 0.409 (9) |
H4XB | 0.4640 | −0.3587 | 0.4566 | 0.125* | 0.409 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0279 (9) | 0.0272 (9) | 0.0509 (11) | 0.0002 (7) | 0.0078 (8) | −0.0002 (8) |
C2 | 0.0307 (11) | 0.0282 (11) | 0.0472 (13) | 0.0005 (8) | 0.0070 (9) | 0.0022 (9) |
N2 | 0.0281 (10) | 0.0306 (10) | 0.0707 (15) | −0.0024 (8) | 0.0124 (9) | −0.0074 (10) |
N3 | 0.0288 (10) | 0.0265 (10) | 0.0534 (12) | −0.0012 (7) | 0.0077 (8) | −0.0021 (8) |
C4 | 0.0303 (11) | 0.0284 (11) | 0.0462 (12) | 0.0021 (8) | 0.0070 (9) | 0.0019 (9) |
O4 | 0.0321 (8) | 0.0289 (8) | 0.0665 (11) | 0.0015 (6) | 0.0122 (7) | −0.0068 (7) |
C5 | 0.0275 (11) | 0.0303 (11) | 0.0526 (13) | 0.0007 (8) | 0.0077 (9) | 0.0010 (9) |
C6 | 0.0296 (11) | 0.0280 (10) | 0.0436 (12) | −0.0006 (8) | 0.0049 (9) | 0.0041 (9) |
N6 | 0.0304 (10) | 0.0309 (10) | 0.0622 (13) | −0.0025 (8) | 0.0089 (9) | −0.0064 (9) |
O2X | 0.135 (3) | 0.0803 (19) | 0.104 (2) | 0.0409 (19) | −0.0184 (19) | −0.0484 (17) |
C5X | 0.185 (6) | 0.062 (2) | 0.061 (2) | −0.016 (3) | 0.016 (3) | 0.0039 (18) |
N1X | 0.106 (5) | 0.047 (3) | 0.052 (3) | 0.004 (3) | 0.013 (3) | −0.002 (2) |
C1X | 0.101 (6) | 0.074 (6) | 0.085 (5) | 0.030 (5) | 0.032 (4) | −0.003 (5) |
C2X | 0.078 (5) | 0.066 (5) | 0.043 (4) | −0.001 (4) | 0.003 (5) | −0.014 (3) |
C3X | 0.072 (4) | 0.140 (8) | 0.071 (4) | −0.008 (5) | 0.000 (3) | −0.031 (5) |
C4X | 0.163 (15) | 0.128 (11) | 0.122 (12) | −0.027 (10) | −0.046 (10) | 0.060 (9) |
N1X' | 0.106 (8) | 0.083 (7) | 0.050 (4) | 0.005 (6) | 0.011 (4) | −0.003 (4) |
C1X' | 0.086 (7) | 0.092 (11) | 0.071 (6) | 0.015 (7) | 0.021 (5) | 0.031 (7) |
C2X' | 0.119 (13) | 0.084 (11) | 0.066 (8) | 0.026 (8) | −0.031 (9) | −0.025 (7) |
C3X' | 0.162 (18) | 0.122 (14) | 0.088 (9) | 0.056 (12) | 0.031 (10) | −0.027 (10) |
C4X' | 0.166 (14) | 0.073 (8) | 0.078 (7) | 0.050 (8) | 0.034 (7) | 0.001 (6) |
N1—C2 | 1.321 (3) | C5X—H5XB | 0.9901 |
N1—C6 | 1.365 (3) | N1X—C2X | 1.293 (8) |
C2—N2 | 1.345 (3) | N1X—C1X | 1.438 (8) |
C2—N3 | 1.345 (3) | C1X—H1X1 | 0.9800 |
N2—H21 | 0.91 (3) | C1X—H1X2 | 0.9800 |
N2—H22 | 0.94 (3) | C1X—H1X3 | 0.9800 |
N3—C4 | 1.391 (3) | C2X—C3X | 1.515 (8) |
N3—H3 | 0.91 (3) | C3X—C4X | 1.507 (9) |
C4—O4 | 1.256 (3) | C3X—H3X1 | 0.9900 |
C4—C5 | 1.397 (3) | C3X—H3X2 | 0.9900 |
C5—C6 | 1.381 (3) | C4X—H4X1 | 0.9900 |
C5—H5 | 0.9500 | C4X—H4X2 | 0.9900 |
C6—N6 | 1.348 (3) | N1X'—C2X' | 1.321 (9) |
N6—H61 | 0.87 (3) | N1X'—C1X' | 1.423 (9) |
N6—H62 | 0.92 (4) | C1X'—H1XA | 0.9800 |
O2X—C2X | 1.189 (7) | C1X'—H1XB | 0.9800 |
O2X—C2X' | 1.228 (9) | C1X'—H1XC | 0.9800 |
C5X—N1X' | 1.381 (7) | C2X'—C3X' | 1.534 (10) |
C5X—N1X | 1.441 (6) | C3X'—C4X' | 1.499 (10) |
C5X—C4X' | 1.571 (9) | C3X'—H3XA | 0.9900 |
C5X—C4X | 1.580 (9) | C3X'—H3XB | 0.9900 |
C5X—H5X1 | 0.9900 | C4X'—H4XA | 0.9900 |
C5X—H5X2 | 0.9900 | C4X'—H4XB | 0.9900 |
C5X—H5XA | 0.9900 | ||
C2—N1—C6 | 116.57 (18) | C2X—N1X—C1X | 124.6 (7) |
N1—C2—N2 | 118.7 (2) | C2X—N1X—C5X | 121.0 (6) |
N1—C2—N3 | 123.2 (2) | C1X—N1X—C5X | 113.3 (6) |
N2—C2—N3 | 118.1 (2) | N1X—C1X—H1X1 | 109.5 |
C2—N2—H21 | 115.3 (18) | N1X—C1X—H1X2 | 109.5 |
C2—N2—H22 | 115.4 (18) | H1X1—C1X—H1X2 | 109.5 |
H21—N2—H22 | 121 (3) | N1X—C1X—H1X3 | 109.5 |
C2—N3—C4 | 122.52 (19) | H1X1—C1X—H1X3 | 109.5 |
C2—N3—H3 | 119.2 (19) | H1X2—C1X—H1X3 | 109.5 |
C4—N3—H3 | 118.3 (19) | O2X—C2X—N1X | 129.7 (8) |
O4—C4—N3 | 117.61 (19) | O2X—C2X—C3X | 119.6 (7) |
O4—C4—C5 | 127.4 (2) | N1X—C2X—C3X | 110.3 (6) |
N3—C4—C5 | 114.99 (19) | C4X—C3X—C2X | 99.1 (7) |
C6—C5—C4 | 119.7 (2) | C4X—C3X—H3X1 | 111.9 |
C6—C5—H5 | 120.1 | C2X—C3X—H3X1 | 111.9 |
C4—C5—H5 | 120.1 | C4X—C3X—H3X2 | 111.9 |
N6—C6—N1 | 114.36 (19) | C2X—C3X—H3X2 | 111.9 |
N6—C6—C5 | 122.6 (2) | H3X1—C3X—H3X2 | 109.6 |
N1—C6—C5 | 122.99 (19) | C3X—C4X—C5X | 113.0 (7) |
C6—N6—H61 | 117 (2) | C3X—C4X—H4X1 | 109.0 |
C6—N6—H62 | 117 (2) | C5X—C4X—H4X1 | 109.0 |
H61—N6—H62 | 120 (3) | C3X—C4X—H4X2 | 109.0 |
N1X'—C5X—N1X | 47.9 (4) | C5X—C4X—H4X2 | 109.0 |
N1X'—C5X—C4X' | 102.2 (6) | H4X1—C4X—H4X2 | 107.8 |
N1X—C5X—C4X' | 54.3 (5) | C2X'—N1X'—C5X | 117.9 (8) |
N1X'—C5X—C4X | 46.7 (6) | C2X'—N1X'—C1X' | 133.8 (10) |
N1X—C5X—C4X | 94.6 (6) | C5X—N1X'—C1X' | 108.2 (8) |
C4X'—C5X—C4X | 148.8 (6) | N1X'—C1X'—H1XA | 109.5 |
N1X'—C5X—H5X1 | 123.6 | N1X'—C1X'—H1XB | 109.5 |
N1X—C5X—H5X1 | 112.8 | H1XA—C1X'—H1XB | 109.5 |
C4X'—C5X—H5X1 | 85.0 | N1X'—C1X'—H1XC | 109.5 |
C4X—C5X—H5X1 | 112.8 | H1XA—C1X'—H1XC | 109.5 |
N1X'—C5X—H5X2 | 126.2 | H1XB—C1X'—H1XC | 109.5 |
N1X—C5X—H5X2 | 112.8 | O2X—C2X'—N1X' | 139.4 (12) |
C4X'—C5X—H5X2 | 81.9 | O2X—C2X'—C3X' | 110.7 (9) |
C4X—C5X—H5X2 | 112.8 | N1X'—C2X'—C3X' | 109.2 (9) |
H5X1—C5X—H5X2 | 110.3 | C4X'—C3X'—C2X' | 102.4 (9) |
N1X'—C5X—H5XA | 111.1 | C4X'—C3X'—H3XA | 111.3 |
N1X—C5X—H5XA | 125.9 | C2X'—C3X'—H3XA | 111.3 |
C4X'—C5X—H5XA | 111.9 | C4X'—C3X'—H3XB | 111.3 |
C4X—C5X—H5XA | 83.3 | C2X'—C3X'—H3XB | 111.3 |
H5X1—C5X—H5XA | 117.6 | H3XA—C3X'—H3XB | 109.2 |
N1X'—C5X—H5XB | 111.4 | C3X'—C4X'—C5X | 107.8 (8) |
N1X—C5X—H5XB | 124.8 | C3X'—C4X'—H4XA | 110.1 |
C4X'—C5X—H5XB | 111.1 | C5X—C4X'—H4XA | 110.1 |
C4X—C5X—H5XB | 87.4 | C3X'—C4X'—H4XB | 110.1 |
H5X2—C5X—H5XB | 116.9 | C5X—C4X'—H4XB | 110.1 |
H5XA—C5X—H5XB | 109.1 | H4XA—C4X'—H4XB | 108.5 |
C6—N1—C2—N2 | −176.8 (2) | O2X—C2X—C3X—C4X | −170.9 (12) |
C6—N1—C2—N3 | 1.1 (3) | N1X—C2X—C3X—C4X | 2.6 (13) |
N1—C2—N3—C4 | 0.0 (4) | C2X—C3X—C4X—C5X | −10.8 (12) |
N2—C2—N3—C4 | 178.0 (2) | N1X'—C5X—C4X—C3X | 15.6 (7) |
C2—N3—C4—O4 | 179.9 (2) | N1X—C5X—C4X—C3X | 13.8 (10) |
C2—N3—C4—C5 | −0.6 (3) | C4X'—C5X—C4X—C3X | 10 (2) |
O4—C4—C5—C6 | 179.5 (2) | N1X—C5X—N1X'—C2X' | 5.6 (15) |
N3—C4—C5—C6 | 0.0 (3) | C4X'—C5X—N1X'—C2X' | 5.2 (16) |
C2—N1—C6—N6 | 179.6 (2) | C4X—C5X—N1X'—C2X' | −172.0 (18) |
C2—N1—C6—C5 | −1.7 (3) | N1X—C5X—N1X'—C1X' | −177.0 (10) |
C4—C5—C6—N6 | 179.7 (2) | C4X'—C5X—N1X'—C1X' | −177.4 (9) |
C4—C5—C6—N1 | 1.1 (3) | C4X—C5X—N1X'—C1X' | 5.4 (13) |
N1X'—C5X—N1X—C2X | −14.8 (9) | C2X—O2X—C2X'—N1X' | −18 (2) |
C4X'—C5X—N1X—C2X | 164.6 (10) | C2X—O2X—C2X'—C3X' | 150 (7) |
C4X—C5X—N1X—C2X | −13.1 (10) | C5X—N1X'—C2X'—O2X | 167 (3) |
N1X'—C5X—N1X—C1X | 177.3 (8) | C1X'—N1X'—C2X'—O2X | −9 (5) |
C4X'—C5X—N1X—C1X | −3.3 (7) | C5X—N1X'—C2X'—C3X' | −1 (2) |
C4X—C5X—N1X—C1X | 179.0 (7) | C1X'—N1X'—C2X'—C3X' | −177.6 (14) |
C2X'—O2X—C2X—N1X | −10 (4) | O2X—C2X'—C3X'—C4X' | −175.7 (18) |
C2X'—O2X—C2X—C3X | 162 (6) | N1X'—C2X'—C3X'—C4X' | −4 (2) |
C1X—N1X—C2X—O2X | −13 (2) | C2X'—C3X'—C4X'—C5X | 6.7 (18) |
C5X—N1X—C2X—O2X | −179.6 (10) | N1X'—C5X—C4X'—C3X' | −7.3 (12) |
C1X—N1X—C2X—C3X | 174.2 (8) | N1X—C5X—C4X'—C3X' | −7.7 (10) |
C5X—N1X—C2X—C3X | 7.7 (13) | C4X—C5X—C4X'—C3X' | −3.2 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O4i | 0.91 (3) | 1.94 (3) | 2.846 (3) | 175 (3) |
N2—H22···N6ii | 0.94 (3) | 2.28 (3) | 3.216 (3) | 177 (3) |
N3—H3···N1ii | 0.91 (3) | 2.02 (3) | 2.922 (3) | 173 (3) |
N6—H61···O2X | 0.87 (3) | 2.01 (3) | 2.850 (3) | 165 (3) |
N6—H62···O4iii | 0.92 (4) | 1.94 (4) | 2.857 (3) | 173 (3) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x, y−1/2, −z+3/2. |
C6H5Cl2N·C4H6N4O·C4H9NO | F(000) = 392 |
Mr = 375.26 | Dx = 1.388 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 23474 reflections |
a = 8.1060 (5) Å | θ = 3.3–26.4° |
b = 9.0448 (5) Å | µ = 0.38 mm−1 |
c = 12.5656 (8) Å | T = 173 K |
β = 102.859 (5)° | Block, colourless |
V = 898.17 (9) Å3 | 0.20 × 0.14 × 0.12 mm |
Z = 2 |
Stoe IPDS II two-circle diffractometer | 3534 independent reflections |
Radiation source: Genix 3D IµS microfocus X-ray source | 3330 reflections with I > 2σ(I) |
Genix 3D multilayer optics monochromator | Rint = 0.046 |
ω scans | θmax = 26.1°, θmin = 3.3° |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | h = −10→10 |
Tmin = 0.794, Tmax = 0.916 | k = −11→11 |
21925 measured reflections | l = −15→15 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0462P)2 + 0.1437P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
3534 reflections | Δρmax = 0.26 e Å−3 |
257 parameters | Δρmin = −0.18 e Å−3 |
17 restraints | Absolute structure: Flack (1983), Number of Bijvoet pairs: 1646 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (5) |
C6H5Cl2N·C4H6N4O·C4H9NO | V = 898.17 (9) Å3 |
Mr = 375.26 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.1060 (5) Å | µ = 0.38 mm−1 |
b = 9.0448 (5) Å | T = 173 K |
c = 12.5656 (8) Å | 0.20 × 0.14 × 0.12 mm |
β = 102.859 (5)° |
Stoe IPDS II two-circle diffractometer | 3534 independent reflections |
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001) | 3330 reflections with I > 2σ(I) |
Tmin = 0.794, Tmax = 0.916 | Rint = 0.046 |
21925 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.080 | Δρmax = 0.26 e Å−3 |
S = 1.10 | Δρmin = −0.18 e Å−3 |
3534 reflections | Absolute structure: Flack (1983), Number of Bijvoet pairs: 1646 |
257 parameters | Absolute structure parameter: 0.04 (5) |
17 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1A | 0.7878 (3) | 0.9517 (2) | 0.87440 (16) | 0.0252 (4) | |
N1A | 0.7379 (3) | 0.8483 (2) | 0.79611 (17) | 0.0352 (5) | |
H1A1 | 0.789 (4) | 0.853 (3) | 0.750 (2) | 0.042* | |
H1A2 | 0.642 (4) | 0.814 (3) | 0.791 (2) | 0.042* | |
C2A | 0.9313 (3) | 1.0404 (3) | 0.87964 (17) | 0.0306 (4) | |
Cl2A | 1.04435 (8) | 1.01771 (7) | 0.77792 (5) | 0.04277 (16) | |
C3A | 0.9862 (3) | 1.1433 (3) | 0.9603 (2) | 0.0407 (6) | |
H3A | 1.0855 | 1.1994 | 0.9610 | 0.049* | |
C4A | 0.8958 (4) | 1.1648 (3) | 1.0406 (2) | 0.0441 (6) | |
H4A | 0.9326 | 1.2354 | 1.0968 | 0.053* | |
C5A | 0.7518 (3) | 1.0823 (3) | 1.03762 (19) | 0.0369 (5) | |
H5A | 0.6876 | 1.0974 | 1.0914 | 0.044* | |
C6A | 0.7011 (3) | 0.9790 (3) | 0.95776 (17) | 0.0298 (5) | |
Cl6A | 0.51908 (8) | 0.87668 (7) | 0.95601 (5) | 0.04686 (18) | |
N1B | 0.56730 (19) | 0.42237 (18) | 0.43752 (13) | 0.0186 (3) | |
C2B | 0.5014 (2) | 0.5401 (2) | 0.47486 (14) | 0.0184 (4) | |
N2B | 0.3341 (2) | 0.5485 (2) | 0.46373 (15) | 0.0250 (4) | |
H21B | 0.269 (3) | 0.468 (3) | 0.439 (2) | 0.030* | |
H22B | 0.292 (3) | 0.620 (3) | 0.496 (2) | 0.030* | |
N3B | 0.5969 (2) | 0.6551 (2) | 0.52280 (13) | 0.0205 (3) | |
H3B | 0.548 (3) | 0.729 (3) | 0.5441 (19) | 0.025* | |
C4B | 0.7719 (2) | 0.6587 (2) | 0.53695 (15) | 0.0192 (4) | |
O4B | 0.84738 (16) | 0.76997 (15) | 0.58309 (12) | 0.0232 (3) | |
C5B | 0.8424 (2) | 0.5367 (2) | 0.49467 (15) | 0.0204 (4) | |
H5B | 0.9609 | 0.5322 | 0.4993 | 0.024* | |
C6B | 0.7383 (2) | 0.4227 (2) | 0.44609 (15) | 0.0183 (4) | |
N6B | 0.7971 (2) | 0.30113 (19) | 0.40550 (15) | 0.0226 (3) | |
H61B | 0.902 (3) | 0.299 (3) | 0.4059 (19) | 0.027* | |
H62B | 0.728 (3) | 0.252 (3) | 0.361 (2) | 0.027* | |
C1X | 0.3033 (3) | −0.0586 (4) | 0.2158 (3) | 0.0550 (8) | |
H11X | 0.2927 | −0.1661 | 0.2077 | 0.082* | 0.635 (9) |
H12X | 0.2497 | −0.0108 | 0.1468 | 0.082* | 0.635 (9) |
H13X | 0.2475 | −0.0258 | 0.2733 | 0.082* | 0.635 (9) |
H4AX | 0.2186 | −0.1377 | 0.2029 | 0.082* | 0.365 (9) |
H4BX | 0.2839 | 0.0056 | 0.2747 | 0.082* | 0.365 (9) |
H4CX | 0.2939 | −0.0003 | 0.1490 | 0.082* | 0.365 (9) |
O2X | 0.5497 (2) | 0.11334 (17) | 0.26385 (14) | 0.0350 (4) | |
C4X | 0.5361 (5) | −0.2831 (3) | 0.2364 (2) | 0.0531 (8) | |
H41X | 0.6320 | −0.3517 | 0.2514 | 0.080* | 0.635 (9) |
H42X | 0.4776 | −0.2908 | 0.1594 | 0.080* | 0.635 (9) |
H43X | 0.4574 | −0.3079 | 0.2827 | 0.080* | 0.635 (9) |
H1AX | 0.4378 | −0.3491 | 0.2226 | 0.080* | 0.365 (9) |
H1BX | 0.5925 | −0.2886 | 0.1751 | 0.080* | 0.365 (9) |
H1CX | 0.6153 | −0.3133 | 0.3037 | 0.080* | 0.365 (9) |
C5X | 0.7811 (3) | −0.0953 (3) | 0.2912 (2) | 0.0437 (6) | |
H51X | 0.8461 | −0.1875 | 0.2990 | 0.066* | 0.635 (9) |
H52X | 0.8058 | −0.0416 | 0.3607 | 0.066* | 0.635 (9) |
H53X | 0.8125 | −0.0340 | 0.2345 | 0.066* | 0.635 (9) |
H5AX | 0.7706 | −0.2032 | 0.2869 | 0.066* | 0.365 (9) |
H5BX | 0.8425 | −0.0604 | 0.2371 | 0.066* | 0.365 (9) |
H5CX | 0.8431 | −0.0668 | 0.3645 | 0.066* | 0.365 (9) |
C2X | 0.4921 (6) | −0.0160 (5) | 0.2469 (3) | 0.0257 (11) | 0.635 (9) |
N3X | 0.5987 (5) | −0.1294 (4) | 0.2602 (2) | 0.0316 (12) | 0.635 (9) |
N3X' | 0.4761 (9) | −0.1240 (8) | 0.2466 (4) | 0.038 (2) | 0.365 (9) |
C2X' | 0.5992 (10) | −0.0249 (8) | 0.2677 (5) | 0.027 (2) | 0.365 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.0255 (9) | 0.0256 (10) | 0.0236 (9) | 0.0033 (8) | 0.0035 (7) | 0.0048 (8) |
N1A | 0.0349 (11) | 0.0404 (12) | 0.0321 (10) | −0.0137 (9) | 0.0111 (8) | −0.0073 (9) |
C2A | 0.0300 (11) | 0.0316 (12) | 0.0317 (10) | −0.0013 (9) | 0.0098 (8) | 0.0011 (10) |
Cl2A | 0.0397 (3) | 0.0499 (4) | 0.0446 (3) | −0.0146 (3) | 0.0218 (2) | −0.0087 (3) |
C3A | 0.0399 (13) | 0.0388 (14) | 0.0439 (13) | −0.0114 (11) | 0.0101 (11) | −0.0060 (11) |
C4A | 0.0530 (16) | 0.0383 (14) | 0.0398 (13) | −0.0056 (12) | 0.0082 (11) | −0.0134 (11) |
C5A | 0.0432 (14) | 0.0371 (13) | 0.0321 (12) | 0.0070 (10) | 0.0117 (10) | −0.0005 (9) |
C6A | 0.0270 (10) | 0.0335 (12) | 0.0295 (10) | 0.0020 (9) | 0.0076 (8) | 0.0076 (9) |
Cl6A | 0.0415 (3) | 0.0562 (4) | 0.0489 (3) | −0.0133 (3) | 0.0229 (3) | −0.0016 (3) |
N1B | 0.0139 (7) | 0.0158 (8) | 0.0268 (8) | −0.0011 (6) | 0.0064 (6) | −0.0005 (6) |
C2B | 0.0158 (8) | 0.0162 (9) | 0.0239 (8) | 0.0006 (7) | 0.0057 (7) | 0.0008 (7) |
N2B | 0.0137 (8) | 0.0217 (9) | 0.0414 (9) | −0.0011 (7) | 0.0096 (7) | −0.0077 (8) |
N3B | 0.0154 (7) | 0.0173 (8) | 0.0306 (8) | 0.0014 (6) | 0.0091 (6) | −0.0022 (7) |
C4B | 0.0161 (8) | 0.0170 (9) | 0.0253 (9) | −0.0006 (7) | 0.0061 (7) | 0.0032 (8) |
O4B | 0.0148 (6) | 0.0213 (7) | 0.0337 (7) | −0.0030 (5) | 0.0059 (5) | −0.0043 (6) |
C5B | 0.0134 (8) | 0.0196 (9) | 0.0296 (9) | 0.0007 (7) | 0.0076 (7) | 0.0011 (8) |
C6B | 0.0156 (8) | 0.0191 (9) | 0.0218 (8) | 0.0013 (7) | 0.0075 (7) | 0.0039 (7) |
N6B | 0.0139 (8) | 0.0195 (8) | 0.0359 (10) | 0.0001 (7) | 0.0084 (7) | −0.0029 (7) |
C1X | 0.0344 (14) | 0.067 (2) | 0.0603 (17) | −0.0076 (13) | 0.0047 (12) | −0.0119 (15) |
O2X | 0.0407 (9) | 0.0252 (8) | 0.0394 (9) | −0.0010 (7) | 0.0097 (7) | −0.0058 (7) |
C4X | 0.085 (2) | 0.0273 (13) | 0.0431 (15) | −0.0061 (13) | 0.0062 (14) | −0.0027 (11) |
C5X | 0.0337 (12) | 0.0548 (17) | 0.0414 (12) | 0.0070 (12) | 0.0057 (10) | 0.0003 (12) |
C2X | 0.029 (2) | 0.025 (3) | 0.0222 (16) | −0.0050 (17) | 0.0049 (15) | −0.0063 (13) |
N3X | 0.040 (3) | 0.021 (2) | 0.0329 (16) | −0.0042 (15) | 0.0063 (14) | −0.0066 (13) |
N3X' | 0.042 (5) | 0.038 (5) | 0.034 (3) | −0.013 (3) | 0.007 (2) | −0.007 (3) |
C2X' | 0.034 (5) | 0.028 (5) | 0.017 (3) | −0.004 (3) | 0.001 (3) | −0.001 (2) |
C1A—N1A | 1.353 (3) | C1X—N3X' | 1.490 (8) |
C1A—C2A | 1.402 (3) | C1X—C2X | 1.542 (5) |
C1A—C6A | 1.407 (3) | C1X—H11X | 0.9800 |
N1A—H1A1 | 0.79 (3) | C1X—H12X | 0.9800 |
N1A—H1A2 | 0.83 (3) | C1X—H13X | 0.9800 |
C2A—C3A | 1.375 (3) | C1X—H4AX | 0.9800 |
C2A—Cl2A | 1.743 (2) | C1X—H4BX | 0.9799 |
C3A—C4A | 1.386 (4) | C1X—H4CX | 0.9802 |
C3A—H3A | 0.9500 | O2X—C2X | 1.260 (5) |
C4A—C5A | 1.378 (4) | O2X—C2X' | 1.311 (8) |
C4A—H4A | 0.9500 | C4X—N3X | 1.487 (5) |
C5A—C6A | 1.366 (3) | C4X—N3X' | 1.533 (8) |
C5A—H5A | 0.9500 | C4X—H41X | 0.9800 |
C6A—Cl6A | 1.738 (2) | C4X—H42X | 0.9800 |
N1B—C2B | 1.323 (2) | C4X—H43X | 0.9800 |
N1B—C6B | 1.366 (2) | C4X—H1AX | 0.9800 |
C2B—N2B | 1.334 (2) | C4X—H1BX | 0.9801 |
C2B—N3B | 1.355 (3) | C4X—H1CX | 0.9799 |
N2B—H21B | 0.91 (3) | C5X—N3X | 1.475 (5) |
N2B—H22B | 0.87 (3) | C5X—C2X' | 1.573 (8) |
N3B—C4B | 1.390 (2) | C5X—H51X | 0.9800 |
N3B—H3B | 0.85 (3) | C5X—H52X | 0.9800 |
C4B—O4B | 1.252 (2) | C5X—H53X | 0.9800 |
C4B—C5B | 1.400 (3) | C5X—H5AX | 0.9800 |
C5B—C6B | 1.385 (3) | C5X—H5BX | 0.9800 |
C5B—H5B | 0.9500 | C5X—H5CX | 0.9800 |
C6B—N6B | 1.344 (3) | C2X—N3X | 1.327 (6) |
N6B—H61B | 0.85 (3) | N3X'—C2X' | 1.324 (11) |
N6B—H62B | 0.83 (3) | ||
N1A—C1A—C2A | 122.7 (2) | H4BX—C1X—H4CX | 109.5 |
N1A—C1A—C6A | 123.0 (2) | N3X—C4X—H41X | 109.5 |
C2A—C1A—C6A | 114.28 (19) | N3X'—C4X—H41X | 146.3 |
C1A—N1A—H1A1 | 112 (2) | N3X—C4X—H42X | 109.5 |
C1A—N1A—H1A2 | 117 (2) | N3X'—C4X—H42X | 93.2 |
H1A1—N1A—H1A2 | 127 (3) | H41X—C4X—H42X | 109.5 |
C3A—C2A—C1A | 123.4 (2) | N3X—C4X—H43X | 109.5 |
C3A—C2A—Cl2A | 118.92 (18) | N3X'—C4X—H43X | 84.6 |
C1A—C2A—Cl2A | 117.64 (16) | H41X—C4X—H43X | 109.5 |
C2A—C3A—C4A | 119.6 (2) | H42X—C4X—H43X | 109.5 |
C2A—C3A—H3A | 120.2 | N3X—C4X—H1AX | 146.4 |
C4A—C3A—H3A | 120.2 | N3X'—C4X—H1AX | 109.0 |
C5A—C4A—C3A | 119.1 (2) | H41X—C4X—H1AX | 103.1 |
C5A—C4A—H4A | 120.5 | H42X—C4X—H1AX | 65.6 |
C3A—C4A—H4A | 120.5 | H43X—C4X—H1AX | 49.8 |
C6A—C5A—C4A | 120.3 (2) | N3X—C4X—H1BX | 90.4 |
C6A—C5A—H5A | 119.9 | N3X'—C4X—H1BX | 109.0 |
C4A—C5A—H5A | 119.9 | H41X—C4X—H1BX | 68.3 |
C5A—C6A—C1A | 123.2 (2) | H42X—C4X—H1BX | 55.2 |
C5A—C6A—Cl6A | 119.31 (18) | H43X—C4X—H1BX | 158.9 |
C1A—C6A—Cl6A | 117.44 (17) | H1AX—C4X—H1BX | 109.5 |
C2B—N1B—C6B | 116.92 (16) | N3X—C4X—H1CX | 87.6 |
N1B—C2B—N2B | 119.33 (17) | N3X'—C4X—H1CX | 110.4 |
N1B—C2B—N3B | 122.67 (16) | H41X—C4X—H1CX | 47.0 |
N2B—C2B—N3B | 117.99 (18) | H42X—C4X—H1CX | 155.7 |
C2B—N2B—H21B | 119.3 (15) | H43X—C4X—H1CX | 79.2 |
C2B—N2B—H22B | 119.1 (17) | H1AX—C4X—H1CX | 109.5 |
H21B—N2B—H22B | 119 (2) | H1BX—C4X—H1CX | 109.5 |
C2B—N3B—C4B | 122.70 (17) | N3X—C5X—H51X | 109.5 |
C2B—N3B—H3B | 119.0 (16) | C2X'—C5X—H51X | 145.5 |
C4B—N3B—H3B | 118.3 (16) | N3X—C5X—H52X | 109.5 |
O4B—C4B—N3B | 117.26 (17) | C2X'—C5X—H52X | 88.0 |
O4B—C4B—C5B | 127.63 (17) | H51X—C5X—H52X | 109.5 |
N3B—C4B—C5B | 115.10 (17) | N3X—C5X—H53X | 109.5 |
C6B—C5B—C4B | 119.56 (16) | C2X'—C5X—H53X | 91.1 |
C6B—C5B—H5B | 120.2 | H51X—C5X—H53X | 109.5 |
C4B—C5B—H5B | 120.2 | H52X—C5X—H53X | 109.5 |
N6B—C6B—N1B | 114.07 (17) | N3X—C5X—H5AX | 73.0 |
N6B—C6B—C5B | 122.93 (16) | C2X'—C5X—H5AX | 109.1 |
N1B—C6B—C5B | 122.98 (17) | H52X—C5X—H5AX | 122.7 |
C6B—N6B—H61B | 117.0 (17) | H53X—C5X—H5AX | 123.8 |
C6B—N6B—H62B | 116.5 (17) | N3X—C5X—H5BX | 121.2 |
H61B—N6B—H62B | 122 (2) | C2X'—C5X—H5BX | 109.9 |
N3X'—C1X—H11X | 71.9 | H51X—C5X—H5BX | 89.9 |
C2X—C1X—H11X | 109.5 | H52X—C5X—H5BX | 115.1 |
N3X'—C1X—H12X | 127.6 | H5AX—C5X—H5BX | 109.5 |
C2X—C1X—H12X | 109.5 | N3X—C5X—H5CX | 125.3 |
H11X—C1X—H12X | 109.5 | C2X'—C5X—H5CX | 109.5 |
N3X'—C1X—H13X | 119.4 | H51X—C5X—H5CX | 88.7 |
C2X—C1X—H13X | 109.5 | H53X—C5X—H5CX | 111.9 |
H11X—C1X—H13X | 109.5 | H5AX—C5X—H5CX | 109.5 |
H12X—C1X—H13X | 109.5 | H5BX—C5X—H5CX | 109.5 |
N3X'—C1X—H4AX | 109.6 | O2X—C2X—N3X | 119.3 (5) |
C2X—C1X—H4AX | 147.5 | O2X—C2X—C1X | 125.7 (4) |
H12X—C1X—H4AX | 91.1 | N3X—C2X—C1X | 114.9 (4) |
H13X—C1X—H4AX | 85.5 | C2X—N3X—C5X | 117.3 (4) |
N3X'—C1X—H4BX | 109.8 | C2X—N3X—C4X | 120.9 (4) |
C2X—C1X—H4BX | 88.7 | C5X—N3X—C4X | 121.7 (3) |
H11X—C1X—H4BX | 129.9 | C2X—N3X—H5AX | 155.5 |
H12X—C1X—H4BX | 107.1 | C4X—N3X—H5AX | 83.6 |
H4AX—C1X—H4BX | 109.5 | C2X'—N3X'—C1X | 114.0 (7) |
N3X'—C1X—H4CX | 109.0 | C2X'—N3X'—C4X | 114.4 (7) |
C2X—C1X—H4CX | 88.1 | C1X—N3X'—C4X | 130.4 (5) |
H11X—C1X—H4CX | 117.1 | O2X—C2X'—N3X' | 115.3 (8) |
H13X—C1X—H4CX | 120.6 | O2X—C2X'—C5X | 131.3 (6) |
H4AX—C1X—H4CX | 109.5 | N3X'—C2X'—C5X | 113.4 (6) |
N1A—C1A—C2A—C3A | −178.2 (2) | C4B—C5B—C6B—N1B | −0.4 (3) |
C6A—C1A—C2A—C3A | 1.4 (3) | C2X'—O2X—C2X—N3X | −1.8 (4) |
N1A—C1A—C2A—Cl2A | 1.8 (3) | C2X'—O2X—C2X—C1X | 175.3 (6) |
C6A—C1A—C2A—Cl2A | −178.56 (15) | N3X'—C1X—C2X—O2X | −172.9 (6) |
C1A—C2A—C3A—C4A | −1.2 (4) | N3X'—C1X—C2X—N3X | 4.4 (4) |
Cl2A—C2A—C3A—C4A | 178.7 (2) | O2X—C2X—N3X—C5X | −1.9 (4) |
C2A—C3A—C4A—C5A | −0.1 (4) | C1X—C2X—N3X—C5X | −179.3 (3) |
C3A—C4A—C5A—C6A | 1.2 (4) | O2X—C2X—N3X—C4X | −177.4 (3) |
C4A—C5A—C6A—C1A | −1.0 (4) | C1X—C2X—N3X—C4X | 5.2 (4) |
C4A—C5A—C6A—Cl6A | −180.0 (2) | C2X'—C5X—N3X—C2X | 2.8 (4) |
N1A—C1A—C6A—C5A | 179.4 (2) | C2X'—C5X—N3X—C4X | 178.3 (5) |
C2A—C1A—C6A—C5A | −0.3 (3) | N3X'—C4X—N3X—C2X | −8.3 (4) |
N1A—C1A—C6A—Cl6A | −1.7 (3) | N3X'—C4X—N3X—C5X | 176.4 (5) |
C2A—C1A—C6A—Cl6A | 178.68 (16) | C2X—C1X—N3X'—C2X' | 1.5 (4) |
C6B—N1B—C2B—N2B | 176.80 (17) | C2X—C1X—N3X'—C4X | −165.0 (8) |
C6B—N1B—C2B—N3B | −2.0 (3) | N3X—C4X—N3X'—C2X' | 2.2 (4) |
N1B—C2B—N3B—C4B | −0.2 (3) | N3X—C4X—N3X'—C1X | 168.7 (8) |
N2B—C2B—N3B—C4B | −179.01 (17) | C2X—O2X—C2X'—N3X' | −4.5 (4) |
C2B—N3B—C4B—O4B | −179.43 (17) | C2X—O2X—C2X'—C5X | 174.2 (9) |
C2B—N3B—C4B—C5B | 2.1 (3) | C1X—N3X'—C2X'—O2X | 3.4 (7) |
O4B—C4B—C5B—C6B | 179.93 (18) | C4X—N3X'—C2X'—O2X | 172.2 (4) |
N3B—C4B—C5B—C6B | −1.8 (3) | C1X—N3X'—C2X'—C5X | −175.5 (4) |
C2B—N1B—C6B—N6B | −179.18 (16) | C4X—N3X'—C2X'—C5X | −6.8 (6) |
C2B—N1B—C6B—C5B | 2.3 (3) | N3X—C5X—C2X'—O2X | −175.7 (8) |
C4B—C5B—C6B—N6B | −178.78 (18) | N3X—C5X—C2X'—N3X' | 3.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A1···O4B | 0.79 (3) | 2.37 (3) | 3.084 (3) | 151 (3) |
N1A—H1A1···Cl2A | 0.79 (3) | 2.51 (3) | 2.971 (2) | 119 (3) |
N1A—H1A2···O2Xi | 0.83 (3) | 2.39 (3) | 3.120 (3) | 149 (3) |
N1A—H1A2···Cl6A | 0.83 (3) | 2.56 (3) | 2.972 (2) | 112 (2) |
N2B—H21B···O4Bii | 0.91 (3) | 2.02 (3) | 2.911 (2) | 167 (2) |
N2B—H22B···N6Bi | 0.87 (3) | 2.27 (3) | 3.135 (3) | 174 (2) |
N3B—H3B···N1Bi | 0.85 (3) | 2.02 (3) | 2.857 (2) | 168 (2) |
N6B—H61B···O4Biii | 0.85 (3) | 2.02 (3) | 2.867 (2) | 173 (2) |
N6B—H62B···O2X | 0.83 (3) | 2.09 (3) | 2.913 (2) | 173 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) −x+2, y−1/2, −z+1. |
M6CU is 3-methyl-6-chlorouracil, DMT is 2,4-diamino-6-methyl-1,3,5-triazine, DCP is 2,6-dichlorophenol, ACM is ???? AIC is 6-aminoisocytosine and DCA is 2,6-dichloroaniline. top
Cocrystal | Experiment 1 (mg; mmol) | Experiment 2 (mg; mmol) | Solvent (µl) | Temperature (°C; K) |
(I) | M6CU: 5; 0.03 | DMT: 1; 0.01 | 260 | 50; 323 |
(II) | M6CU: 5; 0.03 | DMT: 2; 0.02 | 195 | 50; 323 |
(III) | DCP: 52; 0.32 | DMT: 22; 0.17 | 50* | 23; 296 |
(IV) | ACM: 2; 0.01 | AIC: 4; 0.03 | 150 | 23; 296 |
(V) | DCA: 169; 1.04 | AIC: 26; 0.2 | 200 | 23; 296 |
Notes: (*) plus 30 µl DMSO (dimethyl sulfoxide); ACM = 2-amino-4-chloro-6-methylpyrimidine. |
Experimental details
(I) | (II) | (III) | |
Crystal data | |||
Chemical formula | C4H7N5·C4H9NO | C4H7N5·C5H9NO | C6H4Cl2O·C4H7N5 |
Mr | 212.27 | 224.28 | 288.14 |
Crystal system, space group | Orthorhombic, Fdd2 | Orthorhombic, Fdd2 | Triclinic, P1 |
Temperature (K) | 173 | 173 | 173 |
a, b, c (Å) | 23.198 (3), 26.327 (3), 7.288 (1) | 23.178 (2), 26.3327 (17), 7.3428 (5) | 5.0318 (7), 8.5779 (11), 15.008 (2) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 93.929 (11), 96.214 (11), 100.121 (11) |
V (Å3) | 4451.0 (10) | 4481.7 (6) | 631.41 (15) |
Z | 16 | 16 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 | 0.51 |
Crystal size (mm) | 0.14 × 0.12 × 0.08 | 0.19 × 0.14 × 0.10 | 0.19 × 0.12 × 0.06 |
Data collection | |||
Diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) |
Tmin, Tmax | 0.884, 0.922 | 0.623, 0.776 | 0.719, 0.872 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17579, 1139, 996 | 27934, 1147, 1050 | 5126, 2354, 1864 |
Rint | 0.109 | 0.104 | 0.033 |
(sin θ/λ)max (Å−1) | 0.609 | 0.609 | 0.608 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.159, 1.14 | 0.052, 0.103, 1.22 | 0.033, 0.081, 1.03 |
No. of reflections | 1139 | 1147 | 2354 |
No. of parameters | 148 | 159 | 180 |
No. of restraints | 5 | 1 | 0 |
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 |
Δρmax, Δρmin (e Å−3) | 0.24, −0.28 | 0.16, −0.20 | 0.19, −0.21 |
Absolute structure | - | - | ? |
Absolute structure parameter | ? | ? | ? |
(IV) | (V) | |
Crystal data | ||
Chemical formula | C4H6N4O·C5H9NO | C6H5Cl2N·C4H6N4O·C4H9NO |
Mr | 225.26 | 375.26 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21 |
Temperature (K) | 173 | 173 |
a, b, c (Å) | 8.1456 (5), 9.2289 (6), 14.9731 (9) | 8.1060 (5), 9.0448 (5), 12.5656 (8) |
α, β, γ (°) | 90, 96.463 (5), 90 | 90, 102.859 (5), 90 |
V (Å3) | 1118.45 (12) | 898.17 (9) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.38 |
Crystal size (mm) | 0.50 × 0.45 × 0.30 | 0.20 × 0.14 × 0.12 |
Data collection | ||
Diffractometer | Stoe IPDS II two-circle diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | Multi-scan (X-AREA; Stoe & Cie, 2001) | Multi-scan (X-AREA; Stoe & Cie, 2001) |
Tmin, Tmax | 0.869, 0.914 | 0.794, 0.916 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28235, 2098, 1912 | 21925, 3534, 3330 |
Rint | 0.073 | 0.046 |
(sin θ/λ)max (Å−1) | 0.611 | 0.619 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.179, 1.07 | 0.031, 0.080, 1.10 |
No. of reflections | 2098 | 3534 |
No. of parameters | 212 | 257 |
No. of restraints | 32 | 17 |
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 |
Δρmax, Δρmin (e Å−3) | 0.61, −0.41 | 0.26, −0.18 |
Absolute structure | ? | Flack (1983), Number of Bijvoet pairs: 1646 |
Absolute structure parameter | ? | 0.04 (5) |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), 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 |
N2—H21···N5i | 0.89 (2) | 2.15 (3) | 3.037 (5) | 175 (5) |
N2—H22···N3ii | 0.89 (2) | 2.16 (3) | 3.041 (5) | 169 (5) |
N4—H41···N1iii | 0.88 (2) | 2.10 (3) | 2.973 (5) | 174 (6) |
N4—H42···O2X | 0.89 (2) | 2.00 (3) | 2.865 (5) | 163 (5) |
Symmetry codes: (i) x−1/4, −y+3/4, z+1/4; (ii) −x+1, −y+1, z; (iii) x+1/4, −y+3/4, z−1/4. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···N3i | 0.95 (4) | 2.08 (4) | 3.013 (4) | 169 (4) |
N2—H22···N5ii | 0.85 (4) | 2.23 (5) | 3.062 (4) | 168 (4) |
N4—H41···N1iii | 0.85 (5) | 2.14 (5) | 2.982 (4) | 175 (4) |
N4—H42···O2X | 0.88 (4) | 2.09 (4) | 2.922 (4) | 157 (4) |
Symmetry codes: (i) −x+1, −y+1, z; (ii) x−1/4, −y+3/4, z+1/4; (iii) x+1/4, −y+3/4, z−1/4. |
D—H···A | D—H | H···A | D···A | D—H···A |
N4B—H4B1···O1A | 0.83 (2) | 2.68 (2) | 3.060 (2) | 110 (2) |
N4B—H4B1···Cl6A | 0.83 (2) | 3.01 (2) | 3.7354 (17) | 147 (2) |
N2B—H2B1···O1Ai | 0.84 (2) | 2.53 (2) | 3.200 (2) | 139 (2) |
N2B—H2B2···N1Bii | 0.85 (3) | 2.14 (3) | 2.987 (2) | 179 (2) |
N4B—H4B2···N3Bi | 0.87 (3) | 2.11 (3) | 2.977 (2) | 174 (2) |
O1A—H1A···N5Biii | 0.86 (3) | 1.78 (3) | 2.6123 (19) | 160 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O4i | 0.91 (3) | 1.94 (3) | 2.846 (3) | 175 (3) |
N2—H22···N6ii | 0.94 (3) | 2.28 (3) | 3.216 (3) | 177 (3) |
N3—H3···N1ii | 0.91 (3) | 2.02 (3) | 2.922 (3) | 173 (3) |
N6—H61···O2X | 0.87 (3) | 2.01 (3) | 2.850 (3) | 165 (3) |
N6—H62···O4iii | 0.92 (4) | 1.94 (4) | 2.857 (3) | 173 (3) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) −x, y−1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A1···O4B | 0.79 (3) | 2.37 (3) | 3.084 (3) | 151 (3) |
N1A—H1A1···Cl2A | 0.79 (3) | 2.51 (3) | 2.971 (2) | 119 (3) |
N1A—H1A2···O2Xi | 0.83 (3) | 2.39 (3) | 3.120 (3) | 149 (3) |
N1A—H1A2···Cl6A | 0.83 (3) | 2.56 (3) | 2.972 (2) | 112 (2) |
N2B—H21B···O4Bii | 0.91 (3) | 2.02 (3) | 2.911 (2) | 167 (2) |
N2B—H22B···N6Bi | 0.87 (3) | 2.27 (3) | 3.135 (3) | 174 (2) |
N3B—H3B···N1Bi | 0.85 (3) | 2.02 (3) | 2.857 (2) | 168 (2) |
N6B—H61B···O4Biii | 0.85 (3) | 2.02 (3) | 2.867 (2) | 173 (2) |
N6B—H62B···O2X | 0.83 (3) | 2.09 (3) | 2.913 (2) | 173 (2) |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) −x+2, y−1/2, −z+1. |
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