research papers
Nine N-aryl-2-chloronicotinamides: supramolecular structures in one, two and three dimensions
aAgência Córdoba Ciência-Unidad Ceprocor, Córdoba, Argentina, bSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland, cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, dFundação Oswaldo Cruz, Far Manguinhos, Rua Sizenando Nabuco, 100 Manguinhos, 21041-250 Rio de Janeiro-RJ, Brazil, and eInstituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, CP 68563, 21945-970 Rio de Janeiro-RJ, Brazil
*Correspondence e-mail: cg@st-andrews.ac.uk
Structures are reported here for eight further substituted N-aryl-2-chloronicotinamides, 2-ClC5H3NCONHC6H4X-4′. When X = H, compound (I) (C12H9ClN2O), the molecules are linked into sheets by N—H⋯N, C—H⋯π(pyridyl) and C—H⋯π(arene) hydrogen bonds. For X = CH3, compound (II) (C13H11ClN2O, triclinic with Z′ = 2), the molecules are linked into sheets by N—H⋯O, C—H⋯O and C—H⋯π(arene) hydrogen bonds. Compound (III), where X = F, crystallizes as a monohydrate (C12H8ClFN2O·H2O) and sheets are formed by N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds and aromatic π⋯π stacking interactions. Crystals of compound (IV), where X = Cl (C12H8Cl2N2O, monoclinic P21 with Z′ = 4) exhibit inversion the molecules are linked by N—H⋯O hydrogen bonds into four independent chains, linked in pairs by C—H⋯π(arene) hydrogen bonds. When X = Br, compound (V) (C12H8BrClN2O), the molecules are linked into sheets by N—H⋯O and C—H⋯N hydrogen bonds, while in compound (VI), where X = I (C12H8ClIN2O), the molecules are linked into a three-dimensional framework by N—H⋯O and C—H⋯π(arene) hydrogen bonds and an iodo⋯N(pyridyl) interaction. For X = CH3O, compound (VII) (C13H11ClN2O2), the molecules are linked into chains by a single N—H⋯O hydrogen bond. Compound (VIII) (C13H8ClN3O, triclinic with Z′ = 2), where X = CN, forms a complex three-dimensional framework by N—H⋯N, C—H⋯N and C—H⋯O hydrogen bonds and two independent aromatic π⋯π stacking interactions.
Keywords: supramolecular structures; direction-specific intermolecular interactions; hydrogen bonds; vitamin B.
1. Introduction
Nicotinic acid (pyridine-3-carboxylic acid) and nicotinamide (niacinamide, pyridine-3-carboxamide) are two of the principal members of the B-vitamin complex. Niacin, nicotinamide and nicotinic acid have identical vitamin activities, but they have very different pharmacological activities. Nicotinamide, via its major metabolite nicotinamide adenine dinucleotide, is involved in a wide range of biological processes including the production of energy, the synthesis of cholesterol and signal transduction, and the maintenance of the integrity of the genome. Nicotinic acid in pharmacological doses is used as an antihyperlipidemic agent: it also causes vasodilation of cutaneous blood vessels. Nicotinamide has been investigated as an agent for the prevention or delay of the onset of type 1 diabetes mellitus. It also has anti-oxidant, anti-inflammatory and anti-carcinogenic activities, and has putative activity against osteoarthritis and granuloma annulare. We have made a study of the properties and activities of substituted derivatives, 2-chloro-N-(4-X-phenyl)nicotinamides, and here we report the structures and supramolecular arrangements of nine examples having X = H (I), Me (II), F (III), Cl (IV), Br (V), I (VI), OMe (VII) and CN (VIII), and including the recently reported analogue with X = NO2, (IX) (de Souza et al., 2005).
Here we report the molecular and supramolecular structures of eight closely related N-aryl-2-chloronicotinamides, 2-ClC5H3NCONHC6H4X-4′, whose crystallization characteristics prove to be all different, even within the halogen-substituted subset, (III)–(VI), and whose supramolecular structures all prove to be different, with no two utilizing the same combination of direction-specific intermolecular interactions.
2. Experimental
2.1. Synthesis
Samples of (I)–(VIII) were prepared by reaction of equimolar quantities of 2-chloronicotinoyl chloride and the appropriate substituted aniline in tetrahydrofuran solution at ambient temperature in the presence of a catalytic quantity of triethylamine. After stirring for 8 h, the reaction mixtures were neutralized with saturated aqueous sodium hydrogencarbonate solution and the resulting aqueous mixtures were extracted with ethyl acetate (2 × 30 cm3). For each preparation, the organic extracts were combined, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. on silica, using hexane:ethyl acetate gradients (up to 50% ethyl acetate), then yielded the pure products, with yields in the range 80–90%. Crystals of (I), (II) and (IV)–(VIII) suitable for single-crystal X-ray diffraction were grown from solution in ethanol, and crystals of (III) were grown from an aqueous solution: m.p.s: (I) 395–397 K, (II) 432–433 K, (III) 366–367 K, (IV) 421–422 K, (V) 399–400 K, (VI) 448–450 K, (VII) 383–384 K and (VIII) 445–446 K.
2.2. Data collection, structure solution and refinement
Details of cell data, data collection and structure solution and (Bruker, 2004; Cernik et al., 1997; Ferguson, 1999; McArdle, 2003; Otwinowski & Minor, 1997; Sheldrick, 1997a,b, 2003; Hooft, 1999). The space groups for (I), (IV), (V), VI) and (VII) were all assigned uniquely from the crystals of (II), (III) and (VIII) are triclinic, and for each the was selected, and confirmed by the successful structure analysis. The structures were all solved by using SHELXS97 (Sheldrick, 1997a) and refined on F2 with all data using SHELXL97 (Sheldrick, 1997b). A weighting scheme based upon P = [Fo2 + 2Fc2]/3 was employed in order to reduce statistical bias (Wilson, 1976). All H atoms were located from difference maps and all were included in the refinements as riding atoms, with distances C—H 0.95 and N—H 0.88 Å, and with Uiso(H) = 1.2Ueq(C,N). For (V) and (VII), the correct was selected using the (Flack, 1983): the final values were 0.031 (7) and −0.05 (7), respectively. For (IV), where the crystals were all of very poor quality, the 0.54 (11) indicated inversion twinning.
are summarized in Table 1Supramolecular analyses were made and the diagrams were prepared with the aid of PLATON (Spek, 2003). Figs. 1–30 show the independent components of (I)–(VIII) and aspects of their supramolecular structures. Selected torsional angles are given in Table 2 and details of the hydrogen bonding are in Table 3.1
‡In molecule 2 of (II), (IV), (VIII) and (IX) the relevant atom sequence is C32—C33—C37—N41—C41—C42; in molecules 3 and 4 of (IV) the relevant atom sequences are C52—C53—C57—N61—C61—C62 and C72—C73—C77—N81—C81—C82, respectively (see Figs. 5, 12 and 25). §Data from de Souza et al. (2005). |
‡Cg2 is the centroid of ring C21–C26. §Cg3 is the centroid of ring C41–C46. ¶Cg5 is the centroid of ring C81–C86. ††Cg4 is the centroid of ring C61–C66. |
3. Results and discussion
3.1. Crystallization characteristics
Compounds (II) and (VIII) both crystallize with Z′ = 2, while (IV) has Z′= 4; similarly, the 4-nitrophenyl derivative (IX) crystallizes with Z′ = 2 (de Souza et al., 2005). Of the compounds (I)–(VIII) reported here, the 4-fluorophenyl derivative is unique in crystallizing as a monohydrate, although the 2-nitrophenyl analogue reported recently (de Souza et al., 2005) also crystallizes as a stoichiometric monohydrate.
3.2. Molecular conformations
In each of compounds (I)–(VIII), as well as in (IX) (de Souza et al., 2005), the central C—C—N—C spacer unit is nearly planar, as shown by the torsional angles for this unit which are all close to 180°, ranging between 170.0 (3) and −173.4 (2)° (Table 2). However, the aryl ring is often markedly twisted out of this plane, particularly in (II), (IV), (V), (VI) and (VII), while the chloropyridyl is always twisted well away from the plane of the central spacer, being nearly orthogonal to this plane in (II), (VI), (VIII) and (IX). An alternative way to consider the overall conformations is by means of the dihedral angle denoted Δ between the two rings of each molecule, also shown in Table 2. It is striking to note the relationships between the conformations of the four independent molecules in (IV), shown particularly clearly by the dihedral angles Δ: molecules 1 and 2, containing N21 and N41 respectively, are close to being enantiomorphs, as are molecules 3 and 4 containing N61 and N81. However, the relationships between molecules 1 and 3, and between molecules 2 and 4 is that of The wide range of the dihedral angles Δ in (I)–(IX), varying from 10.2 (2)° in (VII) to 89.4 (2)° in molecule 2 of (VIII), indicates that the intramolecular barriers to rotation about the C—C bonds connecting the rings to the central spacer unit are rather readily overcome by the intermolecular forces, in particular by the direction-specific hydrogen bonds. In this way the observed conformations are an indirect reflection of the action of the hydrogen bonds, just as the detailed supramolecular aggregation patterns are a direct reflection of the action of the hydrogen bonds. The bond lengths and angles present no unusual features.
3.3. Supramolecular structures
3.3.1. Compound (I)
In the unsubstituted parent compound, (I) (Fig. 1), the molecules are linked into sheets by a combination of N—H⋯N, C—H⋯π(pyridyl) and C—H⋯π(arene) hydrogen bonds, but N—H⋯O hydrogen bonds are absent (Table 3). The formation of the sheets is most conveniently analysed and described in terms of the chains formed by the N—H⋯N and C—H⋯π(pyridyl) hydrogen bonds, and the linkage of the chains by the C—H⋯π(arene) hydrogen bonds.
The amidic N21 atom in the molecule at (x, y, z) acts as a hydrogen-bond donor to the pyridyl N11 atom in the molecule at (), thus forming a C(7) (Bernstein et al., 1995) chain running parallel to the [001] direction and generated by the c glide plane at x = 0.25. This chain is reinforced by the —H⋯π(pyridyl) hydrogen bond, where the C16 atom in the molecule at (x, y, z) acts as a donor to the pyridyl ring in the molecule at (), thus forming a [001] chain of rings generated by the c glide plane at y = 0.25 (Fig. 2). Four chains of this type pass though each two each in the domains 0.25 < y < 0.75 and −0.25 < y < 0.25, and within each domain, one chain is generated by the c glide plane at 0.25, and the other, antiparallel to the first, is generated by the c glide plane at y = 0.75. A simple centrosymmetric motif serves to link the antiparallel pairs of [001] chains in each domain to form sheets. The C15 atom in the molecule at (x, y, z), which is part of a chain generated by the glide plane at x = 0.25, acts as a hydrogen-bond donor to the phenyl ring in the molecule at (1 - x, 1 - y, 1 - z), which is part of a chain generated by the glide plane at x = 0.75 (Fig. 3). Propagation of this interaction then links all the chains in a given domain of y into a (010) sheet (Fig. 4): two sheets, related to one another by the twofold rotation axes parallel to [001], pass through each but there are no direction-specific interactions between adjacent sheets.
3.3.2. Compound (II)
In the 4-methylphenyl derivative (II), where Z′ = 2 (Fig. 5), the molecules are linked by two independent N—H⋯O hydrogen bonds (Table 3) into C22(8) chains (Fig. 6): it is convenient to refer to molecules containing atoms O1 and O3 as 1 and 2, respectively. Two antiparallel C22(8) chains pass through each and these chains are linked into a chain of edge-fused rings by a single, nearly linear C—H⋯O hydrogen bond, where the pyridyl C35 atom in molecule 2 at (x, y, z) acts as a hydrogen-bond donor to the O1 atom in molecule 1 at (1 - x, 1 - y, 1 - z). Propagation by translation and inversion of these three hydrogen bonds, two of the N—H⋯O type and one of the C—H⋯O type, generates a chain of centrosymmetric, edge-fused rings along (), with R24(16) rings centred at () (n = zero or integer) and R44(20) rings centred at () (n = zero or integer; Fig. 7).
There are two C—H⋯π(arene) hydrogen bonds in the structure of (II) (Table 3): one, having the C34 atom as the donor, lies within the [100] chain of rings, but the other, having C14 as the donor, links the [100] chains into sheets. The C14 atom in molecule 1 at (x, y, z) lies in the chain along (): this atom acts as a donor to the phenyl ring C41–C46 in molecule 2 at (1 - x, 2 - y, -z), which lies in the chain along (). Propagation by inversion of this C—H⋯π(arene) hydrogen bond then links [100] chains into a (011) sheet (Fig. 8). There are no direction-specific interactions between adjacent sheets.
3.3.3. Compound (III)
The 4-fluorophenyl derivative crystallizes as a monohydrate, compound (III), and in the selected ) the two components are linked by an N—H⋯O hydrogen bond: this utilization of the N—H donor site immediately precludes the formation of the characteristic amidic C(4) chain. Instead the molecules are linked into chains of edge-fused rings by a combination of O—H⋯O and O—H⋯N hydrogen bonds (Table 3), and these chains are linked into sheets by a single aromatic π⋯π stacking interaction.
(Fig. 9The water atom O2 at (x, y, z) acts as a hydrogen-bond donor, via H2B, to the amidic atom O1 at (-1 + x, y, z), thus generating by translation a C22(6) chain running parallel to the [100] direction. An antiparallel pair of these C22(6) chains is linked by the N—H⋯O hydrogen bond: the O2 atom at (x, y, z) acts as a donor, via H2A, to the pyridyl N11 atom at (1 - x, 2 - y, 1 - z), thus generating a centrosymmetric R44(16) ring, centred at (). The combination of all the hydrogen bonds then generates, by translation and inversion, a chain of edge-fused R44(16) rings along () (Fig. 10). There are two types of ring within this chain and both are centrosymmetric: those having amidic O atoms as two of the acceptor sites are centred at () (n = zero or integer), and those having water O atoms as two of the acceptor sites are centred at () (n = zero or integer).
The pyridyl rings in the amide molecules at (x, y, z) and (1 - x, 1 - y, 2 - z) are strictly parallel with an of 3.352 (2) Å; the ring-centroid separation is 3.618 (2) Å, corresponding to a nearly ideal ring offset of 1.362 (2) Å. These two amide molecules form parts of the chains of fused rings along () and (), so that propagation by inversion of this stacking interaction forms a [01] chain (Fig. 11), which links the chains of rings into a (011) sheet.
3.3.4. Compound (IV)
We comment here only briefly on the supramolecular aggregation of the 4-chlorophenyl compound (IV). This compound crystallizes in the non-centrosymmetric P21 with Z′ = 4 (Fig. 12), but the crystal quality was extremely poor, with extensive Nonetheless, the main features of the structure are clear enough: each of the four independent molecules forms a C(4) chain by translation along [100], built from N—H⋯O hydrogen bonds (Fig. 13), and these chains are linked in pairs by the C—H⋯ π(arene) hydrogen bonds (Table 3).
3.3.5. Compound (V)
In the 4-bromophenyl compound (V) (Fig. 14), the molecules are linked into isolated sheets by a combination of one N—H⋯O and one C—H⋯N hydrogen bond (Table 3). The amidic N21 atom in the molecule at (x, y, z) acts as a hydrogen-bond donor to the amidic O1 in the molecule at (-1 + x, y, z), so generating by translation a C(4) chain running parallel to the [100] direction (Fig. 15). Four chains of this type pass through each two in each of the domains 0 < z < 0.5 and 0.5 < z < 1.0, and within each of these domains the chains are linked into sheets by a single C—H⋯N hydrogen bond. The aryl C22 atom in the molecule at (x, y, z) acts as a hydrogen-bond donor to the pyridyl N11 atom in the molecule at (), so forming a C(8) chain running parallel to the [010] direction, and generated by the 21 screw axis along () (Fig. 16). The combination of the [100] and [010] chains then generates a (001) sheet in the form of a (4,4) net built from a single type of R44(22) ring (Fig. 17). Two sheets of this type pass through each generated by screw axes at y = 0.25 and y = 0.75, respectively, but there are no direction-specific interactions between adjacent sheets: in particular, aromatic π⋯π stacking interactions and C—H⋯π(arene) hydrogen bonds are absent.
3.3.6. Compound (VI)
The molecules of the 4-iodophenyl compound (VI) (Fig. 18) are linked into sheets by a combination of one N—H⋯O hydrogen bond and one C—H⋯π(arene) hydrogen bond (Table 3) and these sheets are themselves linked by a single iodo⋯N(pyridyl) interaction. The N21 atom in the molecule at (x, y, z) acts as a hydrogen-bond donor to the O1 atom in the molecule at (), so forming a C(4) chain running parallel to the [001] direction, and generated by the c-glide plane at y = 0.25 (Fig. 19). In addition, the pyridyl C15 atom in the molecule at (x, y, z) acts as a hydrogen-bond donor to the aryl ring C21—C26 in the molecule at (), so forming a chain running parallel to the [100] direction and generated by the 21 screw axis along () (Fig. 20). The combination of these two hydrogen-bonded motifs then generates a (010) sheet (Fig. 21): two sheets of this type pass through each in the domains −0.02 < y < 0.52 and 0.48 < y < 1.02. The sole direction-specific interaction between adjacent sheets is an iodo⋯N(pyridyl) interaction, somewhat analogous electronically to an iodo⋯nitro interaction: the I24 atom in the molecule at (x, y, z) forms a short contact with the pyridyl N11 atom in the molecule at (), with dimensions I⋯Ni 3.116 (2) Å, C—I⋯Ni 167.5 (2)° [symmetry code (i) ]. This interaction thus forms a C(10) chain (Starbuck et al., 1999) running parallel to the [010] direction and generated by a b-glide plane at y = 0.75 (Fig. 22): in this manner all the (010) sheets are linked into a continuous three-dimensional array.
3.3.7. Compound (VII)
The supramolecular aggregation of the 4-methoxyphenyl derivative, compound (VII) (Fig. 23), is exceptionally simple. A single N—H⋯O hydrogen bond (Table 3) links the molecules into C(4) chains generated by translation (Fig. 24). Four chain of this type pass through each but there are no direction-specific interactions between adjacent chains: in particular, C—H⋯π(arene) hydrogen bonds and aromatic π⋯π stacking interactions are both absent.
3.3.8. Compound (VIII)
The structure of the 4-cyanophenyl compound (VIII) (Fig. 25) contains N—H⋯N, C—H⋯N and C—H⋯O hydrogen bonds (Table 3), as well as aromatic π⋯π stacking interactions; the resulting three-dimensional structure is of considerable complexity, although it is readily analysed in terms of its constituent one-dimensional sub-structures. Within the the amido N21 atom acts as a hydrogen-bond donor to the cyano N44 atom: similarly, the amido atom N41 at (x, y, z) acts as a donor to the cyano N24 atom at (-2 + x, 1 + y, z), so generating by translation a C22(16) chain running parallel to the [20] direction (Fig. 26). In contrast to the simple chain generated by the hard hydrogen bonds, the soft hydrogen bonds generate both molecular ladders and chains of rings (Bernstein et al., 1995).
Atoms C15 and C35 in the bimolecular aggregate at (x, y, z) act as hydrogen-bond donors respectively to atoms O11 and O31 in the aggregate at (-1 + x, y, z). The individual C—H⋯O hydrogen bonds each generate by translation a C(6) chain along [100] and, together with the N—H⋯N hydrogen bond within the bimolecular aggregate, they generate a chain of edge-fused R44(32) rings (Fig. 27). Alternatively, this motif can be regarded as a molecular ladder, in which the C(6) chains form the uprights, and N—H⋯N hydrogen bonds form part of each rung.
In a similar way, the C25 and C45 atoms in the bimolecular aggregate at (x, y, z) act as hydrogen-bond donors respectively to pyridyl atoms N11 and N31 in the aggregate at (1 + x, -1 + y, z). The individual C—H⋯N hydrogen bonds each generate by translation a C(9) chain along [10] and together with the N—H⋯N hydrogen bond within the bimolecular aggregate they generate a chain of edge-fused R44(28) rings (Fig. 28). As before, this motif can be regarded as a molecular ladder, with the C(9) chains now forming the uprights and with the N—H⋯N hydrogen bonds in the rungs.
Finally, atoms C14 and C34 at (x, y, z) acts as hydrogen-bond donors respectively to atoms O11 at (1 - x, -y, 1 - z) and O31 at (-1 - x, 1 - y, -z), so generating two distinct R22(10) rings, both centrosymmetric, and centred respectively at () and (). The combination of these two rings, together with the N—H⋯N hydrogen bond within the then generates by inversion a chain of rings running parallel to the [21] direction (Fig. 29). This chain, in turn, is reinforced by a combination of two π⋯π stacking interactions. The pyridyl rings containing N11 in the molecules are (x, y, z) and (1 - x, 1 - y, 1 - z) and are parallel with an of 3.426 (2) Å; the ring-centroid separation is 3.589 (2) Å, corresponding to a ring offset of 1.069 (2) Å; similarly, the pyridyl rings containing N31 in the molecules at (x, y, z) and (-1 - x, 2 - y, -z) have an of 3.334 (2) Å, with a ring-centroid separation of 3.658 (2) Å and ring offset of 1.505 (2) Å. These two interactions are centred across the inversion centres at () and (), respectively, and their combination thus generates a second [21] (Fig. 30). The combination of chains along [100], [10], [20] and [21] suffices to generate a continuous three-dimensional framework structure.
3.3.9. Compound (IX)
The structure of the 4-nitrophenyl analogue (IX) has recently been described (de Souza et al., 2005) and here we briefly summarize its supramolecular behaviour. Compound (IX) crystallizes in the P21/n with Z′ = 2, and the molecules are linked by two independent N—H⋯N hydrogen bonds into C22(12) chains in which the two independent molecules alternate: however, the amidic N—H⋯O hydrogen bonds which characterize (II)–(VIII), although not (I), are absent from the structure of (IX).
3.3.10. General comments on the structures
Although the approximately isosteric requirements of methyl and chloro substituents on aryl rings often lead to the isomorphism of corresponding pairs of compounds, the unit-cell dimension and Z′ values (Table 1) for (II) (X = CH3) and (IV) (X = Cl) here are entirely distinct. Likewise, the four 4-halogenophenyl derivatives (III)–(VI) all crystallize in different space groups, one triclinic, two monoclinic and one orthorhombic. In contrast to this, we have recently observed:
|
As the single substituent in the aryl ring is varied within the series (I)–(IX), so too are the direction-specific intermolecular interactions which are manifested in the supramolecular structures. A very common supramolecular motif found in the crystal structures of simple C(4) chains built from N—H⋯O hydrogen bonds, with corresponding C22(8) chains in some cases where Z′ = 2. Such chains occur in (II), where the chain is of C22(8) type; in (IV), where there are four independent C(4) chains, and in (V), (VI) and (VII), each of which forms a single C(4) chain. It is striking how readily this motif can be disrupted when alternative hydrogen-bond acceptor sites are available, so that the amidic N—H donor has a pyridyl N acceptor in each of (I), (VIII) and (IX), while in (III) the water O atom acts as the acceptor to form the amidic N—H bond (Table 3). Despite the acceptor role for the pyridyl N atom manifested in (I), (VIII) and (IX), this potential acceptor is completely inactive in each of (II), (IV) and (VI), while in (III) and (V) this site acts as the acceptor in O—H⋯N and C—H⋯N hydrogen bonds, respectively. No obvious pattern of behaviour can be discerned here and any attempt to rationalize such behaviour would necessarily be largely, if not entirely, speculative: in this connection, it should perhaps be emphasized that the intermolecular forces involved here are all fairly weak and soft, and not readily susceptible to quantitative modelling.
is the formation of simpleFor (IV), where X = Cl, (VII) where X = OMe and (IX) where X = NO2 (de Souza et al., 2005), the supramolecular structures are all one-dimensional, with isolated chains built from N—H⋯O hydrogen bonds in (VII), similar chains linked in pairs by C—H⋯π(arene) hydrogen bonds in (IV), and chains built from N—H⋯N hydrogen bonds in (IX). Compounds (IV) and (IX) differ further in that (IV), where Z′ = 4, contains four independent chains, each containing a single molecular type, whereas (IX), where Z′ = 2, contains a single chain where the two independent molecules alternate.
The structures of compounds (I), where X = H, (II), where X = Me, (III), where X = F, and (V), where X = Br, are all two-dimensional. N—H⋯N hydrogen bonds are present only in the structure of (I); C—H⋯O and C—H⋯π(arene) hydrogen bonds are present only in the structure of (II); O—H⋯O and O—H⋯N hydrogen bonds, and aromatic π⋯π stacking interactions are present only in the structure of (III); and C—H⋯N hydrogen bonds are present only in the structure of (V). For the two compounds with three-dimensional supramolecular structures, there are no direction-specific intermolecular interactions in common: the structure of (VI), where X = I, is built from N—H⋯O and C—H⋯π(arene) hydrogen bonds, and iodo⋯pyridyl interactions, while the structure of (VIII), where X = CN, is built from N—H⋯N, C—H⋯N and C—H⋯O hydrogen bonds.
3.3.11. Compounds closely related to (I)–(IX)
Here we briefly comment on the supramolecular structures of some closely related compounds, including two isomers (X) and (XI) of (IX) (de Souza et al., 2005), and (XII)–(XV) retrieved from the Cambridge Structural Database (CSD; Allen, 2002).
In (X), the only N—H⋯O hydrogen bond is intramolecular, so that again the formation of a C(4) chain has readily been prevented: the molecules of (X) are linked into chains of centrosymmetric edge-fused R22(14) and R44(24) rings by two independent C—H⋯.O hydrogen bonds, while the pyridyl N atom is inactive as an acceptor. In the isomeric compound (XI), which unexpectedly crystallizes as a stoichiometric monohydrate just like compound (III), the amidic N—H bond acts as a hydrogen-bond donor to the water molecule, and these bimolecular aggregates are linked by a combination of O—H⋯N and O—H⋯O hydrogen bonds to form a chain of edge-fused rings containing two different types of R44(16) ring. Thus, despite the different composition and constitutions of (III) and (XI), their supramolecular aggregation patterns show a considerable degree of similarity.
The unsubstituted amide (XII) (CSD code PYDCXA10; Gdaniec et al., 1979), which may be regarded as the parent compound for this whole series, forms simple C(4) chains built from N—H⋯O hydrogen bonds, and these chains are linked in pairs by a centrosymmetric π⋯π stacking interaction. In the dichloro compound (XIII) (CSD code HIFWUO; Jethmalani et al., 1996), a combination of N—H⋯N and C—H⋯N hydrogen bonds generates a C(3)C(6)[R12(7)] chain of rings, but no N—H⋯O hydrogen bonds are present.
The ease with which the C(4) motif can be disrupted, not only by the presence of water molecules in the structure, but also by intramolecular hydrogen bonds, is shown both by (X), and by (XIV) (CSD code MURWUR; Zhang et al., 2002) and (XV) (CSD code ZIKWEX; Pèpe et al., 1995), where the amidic N—H bonds participate respectively in intramolecular N—H⋯N and N—H⋯O hydrogen bonds. The supramolecular structure of (XIV) consists of simple C(6) chains built from C—H⋯O hydrogen bonds, while the structure of (XV) consists of effectively isolated molecules with no direction-specific intermolecular interactions of any kind.
4. Concluding remarks
The variations in the unit-cell dimensions in (I)–(IX) and the consequent absence of any isomorphisms, together with the very wide variations in the active intermolecular interactions and in the resulting supramolecular structures, both for these compounds and for the related compounds (X)–(XV), raise the question of whether supramolecular structures of this type, dependent on weak intermolecular forces, are likely to become reliably predictable in the foreseeable future.
Supporting information
10.1107/S0108768106015497/bm5033sup1.cif
contains datablocks global, I, II, III, IV, V, VI, VII, VIII. DOI:Structure factors: contains datablock 729. DOI: 10.1107/S0108768106015497/bm5033Isup2.fcf
Structure factors: contains datablock 527. DOI: 10.1107/S0108768106015497/bm5033IIsup3.fcf
Structure factors: contains datablock 569. DOI: 10.1107/S0108768106015497/bm5033IIIsup4.fcf
Structure factors: contains datablock 743m. DOI: 10.1107/S0108768106015497/bm5033IVsup5.fcf
Structure factors: contains datablock pmv7. DOI: 10.1107/S0108768106015497/bm5033Vsup6.fcf
Structure factors: contains datablock 744. DOI: 10.1107/S0108768106015497/bm5033VIsup7.fcf
Structure factors: contains datablock 594. DOI: 10.1107/S0108768106015497/bm5033VIIsup8.fcf
Structure factors: contains datablock 745. DOI: 10.1107/S0108768106015497/bm5033VIIIsup9.fcf
Data collection: COLLECT (Hooft, 1999) for (I), (III), (IV), (V), (VI), (VII), (VIII); Bruker APEX2 (Bruker, 2004) for (II). Cell
DENZO (Otwinowski & Minor, 1997) & COLLECT for (I), (III), (IV), (V), (VI), (VII), (VIII); SAINT (Bruker, 2004) for (II). Data reduction: DENZO & COLLECT for (I), (III), (IV), (V), (VI), (VII), (VIII); SAINT for (II). For all compounds, program(s) used to solve structure: OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).C12H9ClN2O | F(000) = 960 |
Mr = 232.66 | Dx = 1.442 Mg m−3 |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 2446 reflections |
a = 13.2296 (6) Å | θ = 3.1–27.5° |
b = 21.0744 (10) Å | µ = 0.33 mm−1 |
c = 7.6898 (16) Å | T = 120 K |
V = 2144.0 (5) Å3 | Needle, colourless |
Z = 8 | 0.24 × 0.09 × 0.02 mm |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 2446 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 1724 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.104 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ & ω scans | h = −16→17 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −27→27 |
Tmin = 0.943, Tmax = 0.993 | l = −9→9 |
17837 measured reflections |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0479P)2 + 1.6007P] where P = (Fo2 + 2Fc2)/3 |
2446 reflections | (Δ/σ)max = 0.001 |
145 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C12H9ClN2O | V = 2144.0 (5) Å3 |
Mr = 232.66 | Z = 8 |
Orthorhombic, Pccn | Mo Kα radiation |
a = 13.2296 (6) Å | µ = 0.33 mm−1 |
b = 21.0744 (10) Å | T = 120 K |
c = 7.6898 (16) Å | 0.24 × 0.09 × 0.02 mm |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 2446 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 1724 reflections with I > 2σ(I) |
Tmin = 0.943, Tmax = 0.993 | Rint = 0.104 |
17837 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.28 e Å−3 |
2446 reflections | Δρmin = −0.28 e Å−3 |
145 parameters |
x | y | z | Uiso*/Ueq | ||
N11 | 0.25408 (16) | 0.57579 (10) | 0.9067 (3) | 0.0262 (5) | |
C12 | 0.32767 (18) | 0.60070 (12) | 0.8111 (4) | 0.0238 (6) | |
Cl1 | 0.31180 (5) | 0.68016 (3) | 0.75558 (10) | 0.0305 (2) | |
C13 | 0.41523 (18) | 0.56871 (12) | 0.7615 (3) | 0.0220 (5) | |
C14 | 0.42677 (19) | 0.50752 (12) | 0.8256 (3) | 0.0248 (6) | |
C15 | 0.3523 (2) | 0.48067 (13) | 0.9271 (3) | 0.0282 (6) | |
C16 | 0.2668 (2) | 0.51593 (13) | 0.9605 (4) | 0.0288 (6) | |
C17 | 0.49778 (19) | 0.59498 (12) | 0.6469 (4) | 0.0246 (6) | |
O1 | 0.58540 (13) | 0.59291 (10) | 0.6968 (3) | 0.0390 (5) | |
N21 | 0.46640 (16) | 0.61551 (10) | 0.4897 (3) | 0.0249 (5) | |
C21 | 0.52498 (19) | 0.64341 (12) | 0.3554 (3) | 0.0235 (6) | |
C22 | 0.4731 (2) | 0.66828 (13) | 0.2137 (4) | 0.0296 (7) | |
C23 | 0.5248 (2) | 0.69702 (13) | 0.0789 (4) | 0.0331 (7) | |
C24 | 0.6292 (2) | 0.70101 (13) | 0.0842 (4) | 0.0295 (6) | |
C25 | 0.6809 (2) | 0.67565 (13) | 0.2231 (4) | 0.0293 (6) | |
C26 | 0.63023 (19) | 0.64704 (12) | 0.3598 (4) | 0.0252 (6) | |
H14 | 0.4862 | 0.4841 | 0.7995 | 0.030* | |
H15 | 0.3597 | 0.4390 | 0.9727 | 0.034* | |
H16 | 0.2139 | 0.4967 | 1.0252 | 0.035* | |
H21 | 0.4012 | 0.6125 | 0.4688 | 0.030* | |
H22 | 0.4015 | 0.6655 | 0.2096 | 0.035* | |
H23 | 0.4887 | 0.7140 | −0.0173 | 0.040* | |
H24 | 0.6650 | 0.7212 | −0.0076 | 0.035* | |
H25 | 0.7526 | 0.6778 | 0.2253 | 0.035* | |
H26 | 0.6667 | 0.6301 | 0.4555 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0225 (11) | 0.0302 (12) | 0.0261 (13) | 0.0000 (10) | 0.0039 (10) | −0.0002 (10) |
C12 | 0.0234 (13) | 0.0253 (13) | 0.0227 (14) | 0.0002 (10) | −0.0028 (11) | 0.0013 (11) |
Cl1 | 0.0259 (3) | 0.0258 (3) | 0.0400 (4) | 0.0033 (3) | 0.0028 (3) | 0.0040 (3) |
C13 | 0.0183 (12) | 0.0277 (13) | 0.0202 (14) | 0.0002 (10) | −0.0021 (11) | 0.0010 (11) |
C14 | 0.0241 (13) | 0.0294 (14) | 0.0210 (14) | 0.0029 (12) | −0.0052 (12) | −0.0030 (11) |
C15 | 0.0333 (15) | 0.0256 (14) | 0.0257 (15) | −0.0025 (12) | −0.0002 (13) | 0.0023 (11) |
C16 | 0.0299 (15) | 0.0317 (14) | 0.0247 (15) | −0.0057 (12) | 0.0040 (12) | 0.0001 (12) |
C17 | 0.0205 (12) | 0.0282 (14) | 0.0250 (15) | 0.0045 (11) | 0.0003 (11) | 0.0008 (11) |
O1 | 0.0193 (10) | 0.0645 (14) | 0.0333 (12) | 0.0000 (10) | −0.0020 (9) | 0.0148 (10) |
N21 | 0.0162 (10) | 0.0334 (13) | 0.0250 (13) | −0.0001 (9) | −0.0004 (10) | 0.0055 (10) |
C21 | 0.0225 (13) | 0.0269 (14) | 0.0213 (15) | −0.0016 (11) | 0.0008 (12) | −0.0021 (11) |
C22 | 0.0198 (13) | 0.0369 (16) | 0.0319 (17) | −0.0011 (11) | −0.0009 (12) | 0.0045 (12) |
C23 | 0.0312 (16) | 0.0367 (16) | 0.0315 (17) | −0.0011 (13) | −0.0018 (13) | 0.0092 (13) |
C24 | 0.0300 (15) | 0.0328 (15) | 0.0257 (15) | −0.0044 (12) | 0.0061 (13) | 0.0018 (12) |
C25 | 0.0237 (14) | 0.0344 (15) | 0.0297 (16) | −0.0042 (12) | 0.0036 (12) | −0.0046 (12) |
C26 | 0.0224 (13) | 0.0280 (14) | 0.0251 (15) | −0.0006 (11) | 0.0002 (12) | −0.0027 (11) |
N11—C12 | 1.328 (3) | N21—C21 | 1.419 (3) |
N11—C16 | 1.338 (3) | N21—H21 | 0.8796 |
C12—C13 | 1.394 (3) | C21—C22 | 1.390 (4) |
C12—Cl1 | 1.741 (3) | C21—C26 | 1.395 (3) |
C13—C14 | 1.389 (3) | C22—C23 | 1.382 (4) |
C13—C17 | 1.509 (4) | C22—H22 | 0.95 |
C14—C15 | 1.378 (4) | C23—C24 | 1.385 (4) |
C14—H14 | 0.95 | C23—H23 | 0.95 |
C15—C16 | 1.378 (4) | C24—C25 | 1.376 (4) |
C15—H15 | 0.95 | C24—H24 | 0.95 |
C16—H16 | 0.95 | C25—C26 | 1.385 (4) |
C17—O1 | 1.222 (3) | C25—H25 | 0.95 |
C17—N21 | 1.349 (3) | C26—H26 | 0.95 |
C12—N11—C16 | 116.9 (2) | C17—N21—H21 | 116.3 |
N11—C12—C13 | 124.7 (2) | C21—N21—H21 | 115.6 |
N11—C12—Cl1 | 115.32 (19) | C22—C21—C26 | 119.4 (2) |
C13—C12—Cl1 | 119.9 (2) | C22—C21—N21 | 117.2 (2) |
C14—C13—C12 | 116.3 (2) | C26—C21—N21 | 123.4 (2) |
C14—C13—C17 | 117.9 (2) | C23—C22—C21 | 120.6 (2) |
C12—C13—C17 | 125.8 (2) | C23—C22—H22 | 119.7 |
C15—C14—C13 | 120.2 (2) | C21—C22—H22 | 119.7 |
C15—C14—H14 | 119.9 | C22—C23—C24 | 119.8 (3) |
C13—C14—H14 | 119.9 | C22—C23—H23 | 120.1 |
C16—C15—C14 | 118.1 (2) | C24—C23—H23 | 120.1 |
C16—C15—H15 | 120.9 | C25—C24—C23 | 119.7 (3) |
C14—C15—H15 | 120.9 | C25—C24—H24 | 120.2 |
N11—C16—C15 | 123.6 (3) | C23—C24—H24 | 120.2 |
N11—C16—H16 | 118.2 | C24—C25—C26 | 121.2 (2) |
C15—C16—H16 | 118.2 | C24—C25—H25 | 119.4 |
O1—C17—N21 | 125.8 (2) | C26—C25—H25 | 119.4 |
O1—C17—C13 | 119.4 (2) | C25—C26—C21 | 119.3 (3) |
N21—C17—C13 | 114.7 (2) | C25—C26—H26 | 120.4 |
C17—N21—C21 | 128.1 (2) | C21—C26—H26 | 120.4 |
C16—N11—C12—C13 | 1.1 (4) | C12—C13—C17—N21 | −56.2 (4) |
C16—N11—C12—Cl1 | −176.12 (19) | O1—C17—N21—C21 | −5.5 (4) |
N11—C12—C13—C14 | −3.4 (4) | C13—C17—N21—C21 | 178.8 (2) |
Cl1—C12—C13—C14 | 173.71 (19) | C17—N21—C21—C22 | −171.8 (2) |
N11—C12—C13—C17 | 177.3 (2) | C17—N21—C21—C26 | 8.0 (4) |
Cl1—C12—C13—C17 | −5.7 (4) | C26—C21—C22—C23 | −0.7 (4) |
C12—C13—C14—C15 | 2.3 (4) | N21—C21—C22—C23 | 179.1 (2) |
C17—C13—C14—C15 | −178.3 (2) | C21—C22—C23—C24 | 0.2 (4) |
C13—C14—C15—C16 | 0.7 (4) | C22—C23—C24—C25 | 0.7 (4) |
C12—N11—C16—C15 | 2.4 (4) | C23—C24—C25—C26 | −1.1 (4) |
C14—C15—C16—N11 | −3.2 (4) | C24—C25—C26—C21 | 0.6 (4) |
C14—C13—C17—O1 | −51.6 (4) | C22—C21—C26—C25 | 0.3 (4) |
C12—C13—C17—O1 | 127.8 (3) | N21—C21—C26—C25 | −179.5 (2) |
C14—C13—C17—N21 | 124.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···N11i | 0.88 | 2.25 | 3.101 (3) | 164 |
C15—H15···Cg1ii | 0.95 | 2.89 | 3.535 (3) | 126 |
C16—H16···Cg2iii | 0.95 | 2.87 | 3.464 (3) | 121 |
Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y, z+1/2. |
C13H11ClN2O | Z = 4 |
Mr = 246.69 | F(000) = 512 |
Triclinic, P1 | Dx = 1.390 Mg m−3 |
Hall symbol: -P 1 | Synchrotron radiation, λ = 0.67510 Å |
a = 9.6824 (6) Å | Cell parameters from 6881 reflections |
b = 11.3082 (7) Å | θ = 2.1–28.8° |
c = 11.5139 (7) Å | µ = 0.31 mm−1 |
α = 77.453 (2)° | T = 120 K |
β = 73.445 (2)° | Needle, colourless |
γ = 87.978 (2)° | 0.10 × 0.02 × 0.02 mm |
V = 1179.07 (13) Å3 |
Bruker SMART APEX2 CCD diffractometer | 6881 independent reflections |
Radiation source: Daresbury SRS station 9.8, (Cernik et al., 1997) | 5217 reflections with ( > 2σ(I) |
Silicon 111 monochromator | Rint = 0.022 |
fine–slice ω scans | θmax = 28.8°, θmin = 2.1° |
Absorption correction: multi-scan Bruker SADABS (Bruker, 2004) | h = −13→13 |
Tmin = 0.970, Tmax = 0.994 | k = −16→16 |
12982 measured reflections | l = −16→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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0648P)2 + 0.3225P] where P = (Fo2 + 2Fc2)/3 |
6881 reflections | (Δ/σ)max = 0.001 |
309 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C13H11ClN2O | γ = 87.978 (2)° |
Mr = 246.69 | V = 1179.07 (13) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.6824 (6) Å | Synchrotron radiation, λ = 0.67510 Å |
b = 11.3082 (7) Å | µ = 0.31 mm−1 |
c = 11.5139 (7) Å | T = 120 K |
α = 77.453 (2)° | 0.10 × 0.02 × 0.02 mm |
β = 73.445 (2)° |
Bruker SMART APEX2 CCD diffractometer | 6881 independent reflections |
Absorption correction: multi-scan Bruker SADABS (Bruker, 2004) | 5217 reflections with ( > 2σ(I) |
Tmin = 0.970, Tmax = 0.994 | Rint = 0.022 |
12982 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.43 e Å−3 |
6881 reflections | Δρmin = −0.30 e Å−3 |
309 parameters |
x | y | z | Uiso*/Ueq | ||
N11 | 0.86915 (14) | 0.73134 (12) | −0.08967 (11) | 0.0221 (3) | |
C12 | 0.84419 (15) | 0.70831 (13) | 0.03187 (12) | 0.0183 (3) | |
Cl1 | 0.83100 (5) | 0.55573 (3) | 0.10547 (3) | 0.02910 (11) | |
C13 | 0.83069 (14) | 0.79583 (13) | 0.10341 (12) | 0.0168 (3) | |
C14 | 0.83825 (17) | 0.91586 (14) | 0.04073 (13) | 0.0220 (3) | |
C15 | 0.86423 (18) | 0.94293 (14) | −0.08708 (13) | 0.0245 (3) | |
C16 | 0.88058 (17) | 0.84842 (14) | −0.14807 (13) | 0.0236 (3) | |
C17 | 0.82579 (15) | 0.76179 (13) | 0.23844 (12) | 0.0173 (3) | |
O1 | 0.93912 (11) | 0.74347 (11) | 0.26770 (9) | 0.0255 (2) | |
N21 | 0.69517 (13) | 0.75458 (11) | 0.31986 (10) | 0.0182 (2) | |
C21 | 0.66503 (14) | 0.71569 (13) | 0.45110 (12) | 0.0168 (3) | |
C22 | 0.54054 (15) | 0.64547 (14) | 0.51422 (13) | 0.0201 (3) | |
C23 | 0.50576 (16) | 0.60308 (14) | 0.64181 (13) | 0.0223 (3) | |
C24 | 0.59492 (16) | 0.62974 (14) | 0.70977 (12) | 0.0209 (3) | |
C25 | 0.71711 (16) | 0.70342 (14) | 0.64523 (13) | 0.0214 (3) | |
C26 | 0.75349 (15) | 0.74657 (14) | 0.51730 (13) | 0.0196 (3) | |
C241 | 0.56166 (18) | 0.57879 (16) | 0.84700 (13) | 0.0274 (3) | |
N31 | 0.09859 (14) | 0.76364 (12) | 0.58897 (11) | 0.0225 (3) | |
C32 | 0.17080 (16) | 0.79085 (13) | 0.47011 (13) | 0.0192 (3) | |
Cl3 | 0.20022 (5) | 0.94486 (3) | 0.40386 (4) | 0.03240 (11) | |
C33 | 0.22193 (15) | 0.70691 (13) | 0.39653 (12) | 0.0175 (3) | |
C34 | 0.19083 (15) | 0.58576 (13) | 0.45303 (13) | 0.0200 (3) | |
C35 | 0.11540 (16) | 0.55384 (14) | 0.57837 (13) | 0.0215 (3) | |
C36 | 0.07258 (16) | 0.64550 (14) | 0.64210 (13) | 0.0219 (3) | |
C37 | 0.31481 (15) | 0.74411 (14) | 0.26399 (12) | 0.0194 (3) | |
O3 | 0.44343 (12) | 0.76878 (14) | 0.24022 (10) | 0.0373 (3) | |
N41 | 0.24535 (12) | 0.74497 (11) | 0.17848 (10) | 0.0171 (2) | |
C41 | 0.30028 (14) | 0.78264 (13) | 0.04773 (12) | 0.0164 (3) | |
C42 | 0.21841 (15) | 0.75010 (13) | −0.02321 (12) | 0.0192 (3) | |
C43 | 0.25670 (16) | 0.79412 (14) | −0.15074 (13) | 0.0211 (3) | |
C44 | 0.37751 (16) | 0.87086 (14) | −0.21107 (12) | 0.0205 (3) | |
C441 | 0.41532 (19) | 0.92274 (16) | −0.34831 (13) | 0.0274 (3) | |
C45 | 0.46144 (16) | 0.89806 (14) | −0.13930 (13) | 0.0222 (3) | |
C46 | 0.42436 (15) | 0.85517 (14) | −0.01134 (12) | 0.0204 (3) | |
H14 | 0.8257 | 0.9791 | 0.0850 | 0.026* | |
H15 | 0.8707 | 1.0247 | −0.1318 | 0.029* | |
H16 | 0.9010 | 0.8674 | −0.2359 | 0.028* | |
H21 | 0.6227 | 0.7543 | 0.2879 | 0.022* | |
H22 | 0.4787 | 0.6263 | 0.4696 | 0.024* | |
H23 | 0.4201 | 0.5553 | 0.6836 | 0.027* | |
H25 | 0.7774 | 0.7248 | 0.6901 | 0.026* | |
H26 | 0.8375 | 0.7964 | 0.4756 | 0.024* | |
H24A | 0.5336 | 0.4928 | 0.8650 | 0.041* | |
H24B | 0.4824 | 0.6230 | 0.8913 | 0.041* | |
H24C | 0.6473 | 0.5873 | 0.8741 | 0.041* | |
H34 | 0.2208 | 0.5249 | 0.4065 | 0.024* | |
H35 | 0.0939 | 0.4713 | 0.6190 | 0.026* | |
H36 | 0.0222 | 0.6238 | 0.7279 | 0.026* | |
H41 | 0.1522 | 0.7281 | 0.2078 | 0.021* | |
H42 | 0.1362 | 0.6976 | 0.0160 | 0.023* | |
H43 | 0.1997 | 0.7717 | −0.1978 | 0.025* | |
H44A | 0.3280 | 0.9264 | −0.3758 | 0.041* | |
H44B | 0.4851 | 0.8711 | −0.3923 | 0.041* | |
H44C | 0.4575 | 1.0045 | −0.3663 | 0.041* | |
H45 | 0.5464 | 0.9473 | −0.1790 | 0.027* | |
H46 | 0.4832 | 0.8752 | 0.0354 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0278 (7) | 0.0255 (6) | 0.0147 (5) | 0.0004 (5) | −0.0070 (5) | −0.0064 (5) |
C12 | 0.0191 (6) | 0.0206 (7) | 0.0149 (6) | −0.0015 (5) | −0.0044 (5) | −0.0036 (5) |
Cl1 | 0.0429 (2) | 0.02044 (19) | 0.02131 (18) | −0.00353 (15) | −0.00605 (15) | −0.00230 (14) |
C13 | 0.0156 (6) | 0.0228 (7) | 0.0118 (6) | 0.0001 (5) | −0.0032 (5) | −0.0044 (5) |
C14 | 0.0279 (7) | 0.0226 (7) | 0.0160 (6) | 0.0040 (6) | −0.0058 (5) | −0.0067 (5) |
C15 | 0.0337 (8) | 0.0229 (7) | 0.0154 (6) | 0.0049 (6) | −0.0068 (6) | −0.0021 (5) |
C16 | 0.0298 (8) | 0.0280 (8) | 0.0131 (6) | 0.0044 (6) | −0.0067 (5) | −0.0043 (5) |
C17 | 0.0175 (6) | 0.0214 (7) | 0.0132 (6) | −0.0003 (5) | −0.0043 (5) | −0.0043 (5) |
O1 | 0.0162 (5) | 0.0439 (7) | 0.0158 (5) | 0.0009 (4) | −0.0056 (4) | −0.0039 (4) |
N21 | 0.0159 (5) | 0.0283 (6) | 0.0115 (5) | 0.0006 (4) | −0.0051 (4) | −0.0050 (4) |
C21 | 0.0171 (6) | 0.0238 (7) | 0.0103 (5) | 0.0021 (5) | −0.0033 (5) | −0.0066 (5) |
C22 | 0.0180 (6) | 0.0285 (7) | 0.0147 (6) | −0.0018 (5) | −0.0052 (5) | −0.0054 (5) |
C23 | 0.0203 (7) | 0.0289 (8) | 0.0152 (6) | −0.0019 (6) | −0.0019 (5) | −0.0032 (5) |
C24 | 0.0238 (7) | 0.0260 (7) | 0.0124 (6) | 0.0050 (5) | −0.0039 (5) | −0.0056 (5) |
C25 | 0.0220 (7) | 0.0302 (8) | 0.0153 (6) | 0.0020 (6) | −0.0071 (5) | −0.0095 (5) |
C26 | 0.0181 (6) | 0.0270 (7) | 0.0157 (6) | −0.0011 (5) | −0.0052 (5) | −0.0075 (5) |
C241 | 0.0318 (8) | 0.0363 (9) | 0.0125 (6) | 0.0040 (7) | −0.0049 (6) | −0.0042 (6) |
N31 | 0.0278 (7) | 0.0256 (6) | 0.0133 (5) | 0.0024 (5) | −0.0043 (5) | −0.0048 (5) |
C32 | 0.0227 (7) | 0.0205 (7) | 0.0141 (6) | 0.0004 (5) | −0.0063 (5) | −0.0016 (5) |
Cl3 | 0.0471 (3) | 0.0213 (2) | 0.02420 (19) | −0.00033 (16) | −0.00680 (17) | 0.00040 (14) |
C33 | 0.0159 (6) | 0.0259 (7) | 0.0115 (5) | 0.0000 (5) | −0.0056 (5) | −0.0029 (5) |
C34 | 0.0197 (7) | 0.0243 (7) | 0.0172 (6) | 0.0008 (5) | −0.0054 (5) | −0.0071 (5) |
C35 | 0.0220 (7) | 0.0228 (7) | 0.0177 (6) | −0.0005 (5) | −0.0055 (5) | −0.0001 (5) |
C36 | 0.0228 (7) | 0.0281 (8) | 0.0133 (6) | 0.0004 (6) | −0.0045 (5) | −0.0024 (5) |
C37 | 0.0170 (6) | 0.0294 (7) | 0.0116 (6) | 0.0009 (5) | −0.0048 (5) | −0.0029 (5) |
O3 | 0.0172 (5) | 0.0745 (10) | 0.0175 (5) | −0.0082 (5) | −0.0072 (4) | 0.0001 (6) |
N41 | 0.0150 (5) | 0.0259 (6) | 0.0103 (5) | −0.0014 (4) | −0.0032 (4) | −0.0039 (4) |
C41 | 0.0167 (6) | 0.0229 (7) | 0.0101 (5) | 0.0019 (5) | −0.0038 (5) | −0.0049 (5) |
C42 | 0.0178 (6) | 0.0260 (7) | 0.0147 (6) | −0.0001 (5) | −0.0046 (5) | −0.0060 (5) |
C43 | 0.0226 (7) | 0.0303 (8) | 0.0137 (6) | 0.0034 (6) | −0.0076 (5) | −0.0089 (5) |
C44 | 0.0242 (7) | 0.0251 (7) | 0.0116 (6) | 0.0037 (5) | −0.0040 (5) | −0.0045 (5) |
C441 | 0.0341 (9) | 0.0335 (9) | 0.0121 (6) | 0.0041 (7) | −0.0046 (6) | −0.0031 (6) |
C45 | 0.0226 (7) | 0.0287 (8) | 0.0132 (6) | −0.0036 (6) | −0.0024 (5) | −0.0027 (5) |
C46 | 0.0197 (7) | 0.0281 (7) | 0.0139 (6) | −0.0034 (5) | −0.0048 (5) | −0.0051 (5) |
N11—C12 | 1.3182 (17) | N31—C32 | 1.3203 (17) |
N11—C16 | 1.341 (2) | N31—C36 | 1.3428 (19) |
C12—C13 | 1.3996 (19) | C32—C33 | 1.393 (2) |
C12—Cl1 | 1.7407 (15) | C32—Cl3 | 1.7407 (15) |
C13—C14 | 1.386 (2) | C33—C34 | 1.386 (2) |
C13—C17 | 1.5056 (18) | C33—C37 | 1.5101 (18) |
C14—C15 | 1.3861 (19) | C34—C35 | 1.3921 (19) |
C14—H14 | 0.95 | C34—H34 | 0.95 |
C15—C16 | 1.382 (2) | C35—C36 | 1.383 (2) |
C15—H15 | 0.95 | C35—H35 | 0.95 |
C16—H16 | 0.95 | C36—H36 | 0.95 |
C17—O1 | 1.2348 (16) | C37—O3 | 1.2251 (18) |
C17—N21 | 1.3355 (17) | C37—N41 | 1.3395 (17) |
N21—C21 | 1.4251 (16) | N41—C41 | 1.4184 (16) |
N21—H21 | 0.8803 | N41—H41 | 0.8803 |
C21—C22 | 1.3890 (19) | C41—C46 | 1.3928 (19) |
C21—C26 | 1.3948 (18) | C41—C42 | 1.3969 (18) |
C22—C23 | 1.3874 (19) | C42—C43 | 1.3880 (19) |
C22—H22 | 0.95 | C42—H42 | 0.95 |
C23—C24 | 1.398 (2) | C43—C44 | 1.397 (2) |
C23—H23 | 0.95 | C43—H43 | 0.95 |
C24—C25 | 1.395 (2) | C44—C45 | 1.396 (2) |
C24—C241 | 1.5032 (19) | C44—C441 | 1.5026 (19) |
C25—C26 | 1.3914 (19) | C441—H44A | 0.98 |
C25—H25 | 0.95 | C441—H44B | 0.98 |
C26—H26 | 0.95 | C441—H44C | 0.98 |
C241—H24A | 0.98 | C45—C46 | 1.3911 (19) |
C241—H24B | 0.98 | C45—H45 | 0.95 |
C241—H24C | 0.98 | C46—H46 | 0.95 |
C12—N11—C16 | 116.68 (13) | C32—N31—C36 | 116.89 (13) |
N11—C12—C13 | 125.25 (13) | N31—C32—C33 | 125.15 (13) |
N11—C12—Cl1 | 115.85 (11) | N31—C32—Cl3 | 115.60 (11) |
C13—C12—Cl1 | 118.90 (10) | C33—C32—Cl3 | 119.24 (11) |
C14—C13—C12 | 116.57 (12) | C34—C33—C32 | 116.74 (12) |
C14—C13—C17 | 121.50 (12) | C34—C33—C37 | 120.95 (13) |
C12—C13—C17 | 121.55 (12) | C32—C33—C37 | 122.20 (13) |
C13—C14—C15 | 119.45 (13) | C33—C34—C35 | 119.58 (13) |
C13—C14—H14 | 120.3 | C33—C34—H34 | 120.2 |
C15—C14—H14 | 120.3 | C35—C34—H34 | 120.2 |
C16—C15—C14 | 118.57 (14) | C36—C35—C34 | 118.23 (14) |
C16—C15—H15 | 120.7 | C36—C35—H35 | 120.9 |
C14—C15—H15 | 120.7 | C34—C35—H35 | 120.9 |
N11—C16—C15 | 123.40 (13) | N31—C36—C35 | 123.37 (13) |
N11—C16—H16 | 118.3 | N31—C36—H36 | 118.3 |
C15—C16—H16 | 118.3 | C35—C36—H36 | 118.3 |
O1—C17—N21 | 124.14 (12) | O3—C37—N41 | 124.47 (13) |
O1—C17—C13 | 119.67 (12) | O3—C37—C33 | 121.01 (12) |
N21—C17—C13 | 116.18 (12) | N41—C37—C33 | 114.51 (12) |
C17—N21—C21 | 125.42 (12) | C37—N41—C41 | 127.77 (12) |
C17—N21—H21 | 114.9 | C37—N41—H41 | 115.4 |
C21—N21—H21 | 117.4 | C41—N41—H41 | 116.4 |
C22—C21—C26 | 119.55 (12) | C46—C41—C42 | 119.37 (12) |
C22—C21—N21 | 117.58 (12) | C46—C41—N41 | 123.70 (12) |
C26—C21—N21 | 122.86 (12) | C42—C41—N41 | 116.80 (12) |
C23—C22—C21 | 120.59 (13) | C43—C42—C41 | 120.29 (13) |
C23—C22—H22 | 119.7 | C43—C42—H42 | 119.9 |
C21—C22—H22 | 119.7 | C41—C42—H42 | 119.9 |
C22—C23—C24 | 120.94 (14) | C42—C43—C44 | 121.15 (13) |
C22—C23—H23 | 119.5 | C42—C43—H43 | 119.4 |
C24—C23—H23 | 119.5 | C44—C43—H43 | 119.4 |
C25—C24—C23 | 117.58 (13) | C45—C44—C43 | 117.66 (12) |
C25—C24—C241 | 121.29 (14) | C45—C44—C441 | 121.21 (14) |
C23—C24—C241 | 121.12 (14) | C43—C44—C441 | 121.13 (13) |
C26—C25—C24 | 122.13 (13) | C44—C441—H44A | 109.5 |
C26—C25—H25 | 118.9 | C44—C441—H44B | 109.5 |
C24—C25—H25 | 118.9 | H44A—C441—H44B | 109.5 |
C25—C26—C21 | 119.15 (13) | C44—C441—H44C | 109.5 |
C25—C26—H26 | 120.4 | H44A—C441—H44C | 109.5 |
C21—C26—H26 | 120.4 | H44B—C441—H44C | 109.5 |
C24—C241—H24A | 109.5 | C46—C45—C44 | 121.91 (13) |
C24—C241—H24B | 109.5 | C46—C45—H45 | 119.0 |
H24A—C241—H24B | 109.5 | C44—C45—H45 | 119.0 |
C24—C241—H24C | 109.5 | C45—C46—C41 | 119.50 (13) |
H24A—C241—H24C | 109.5 | C45—C46—H46 | 120.2 |
H24B—C241—H24C | 109.5 | C41—C46—H46 | 120.2 |
C16—N11—C12—C13 | −0.8 (2) | C36—N31—C32—C33 | −0.2 (2) |
C16—N11—C12—Cl1 | −179.58 (11) | C36—N31—C32—Cl3 | 179.10 (11) |
N11—C12—C13—C14 | 2.9 (2) | N31—C32—C33—C34 | 1.6 (2) |
Cl1—C12—C13—C14 | −178.36 (11) | Cl3—C32—C33—C34 | −177.70 (10) |
N11—C12—C13—C17 | −170.10 (13) | N31—C32—C33—C37 | −174.61 (13) |
Cl1—C12—C13—C17 | 8.60 (18) | Cl3—C32—C33—C37 | 6.09 (19) |
C12—C13—C14—C15 | −2.7 (2) | C32—C33—C34—C35 | −1.8 (2) |
C17—C13—C14—C15 | 170.38 (14) | C37—C33—C34—C35 | 174.50 (13) |
C13—C14—C15—C16 | 0.6 (2) | C33—C34—C35—C36 | 0.7 (2) |
C12—N11—C16—C15 | −1.6 (2) | C32—N31—C36—C35 | −1.0 (2) |
C14—C15—C16—N11 | 1.7 (2) | C34—C35—C36—N31 | 0.8 (2) |
C14—C13—C17—O1 | −91.64 (18) | C34—C33—C37—O3 | −97.98 (19) |
C12—C13—C17—O1 | 81.05 (18) | C32—C33—C37—O3 | 78.1 (2) |
C14—C13—C17—N21 | 87.78 (17) | C34—C33—C37—N41 | 80.81 (17) |
C12—C13—C17—N21 | −99.53 (16) | C32—C33—C37—N41 | −103.14 (16) |
O1—C17—N21—C21 | −5.3 (2) | O3—C37—N41—C41 | −5.5 (3) |
C13—C17—N21—C21 | 175.30 (13) | C33—C37—N41—C41 | 175.77 (13) |
C17—N21—C21—C22 | −141.82 (15) | C37—N41—C41—C46 | −18.0 (2) |
C17—N21—C21—C26 | 39.1 (2) | C37—N41—C41—C42 | 166.05 (14) |
C26—C21—C22—C23 | −1.8 (2) | C46—C41—C42—C43 | −2.9 (2) |
N21—C21—C22—C23 | 179.06 (13) | N41—C41—C42—C43 | 173.22 (13) |
C21—C22—C23—C24 | −0.1 (2) | C41—C42—C43—C44 | 0.4 (2) |
C22—C23—C24—C25 | 2.0 (2) | C42—C43—C44—C45 | 2.4 (2) |
C22—C23—C24—C241 | −176.85 (14) | C42—C43—C44—C441 | −177.36 (14) |
C23—C24—C25—C26 | −2.1 (2) | C43—C44—C45—C46 | −2.6 (2) |
C241—C24—C25—C26 | 176.79 (14) | C441—C44—C45—C46 | 177.08 (14) |
C24—C25—C26—C21 | 0.2 (2) | C44—C45—C46—C41 | 0.2 (2) |
C22—C21—C26—C25 | 1.8 (2) | C42—C41—C46—C45 | 2.6 (2) |
N21—C21—C26—C25 | −179.17 (13) | N41—C41—C46—C45 | −173.22 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O3 | 0.88 | 1.96 | 2.827 (2) | 170 |
N41—H41···O1i | 0.88 | 1.99 | 2.847 (2) | 163 |
C35—H35···O1ii | 0.95 | 2.48 | 3.424 (2) | 174 |
C14—H14···Cg3iii | 0.95 | 2.69 | 3.398 (2) | 132 |
C34—H34···Cg2ii | 0.95 | 2.63 | 3.398 (2) | 138 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+2, −z. |
C12H8ClFN2O·H2O | Z = 2 |
Mr = 268.67 | F(000) = 276 |
Triclinic, P1 | Dx = 1.504 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8033 (4) Å | Cell parameters from 2720 reflections |
b = 8.1303 (3) Å | θ = 3.3–27.8° |
c = 11.5356 (6) Å | µ = 0.33 mm−1 |
α = 84.032 (3)° | T = 120 K |
β = 84.297 (2)° | Plate, colourless |
γ = 69.569 (3)° | 0.18 × 0.16 × 0.03 mm |
V = 593.32 (5) Å3 |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 2720 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 1943 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.8°, θmin = 3.3° |
ϕ & ω scans | h = −8→8 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick,. 2003) | k = −9→10 |
Tmin = 0.933, Tmax = 0.990 | l = −14→14 |
12303 measured reflections |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0536P)2 + 0.1705P] where P = (Fo2 + 2Fc2)/3 |
2720 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C12H8ClFN2O·H2O | γ = 69.569 (3)° |
Mr = 268.67 | V = 593.32 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.8033 (4) Å | Mo Kα radiation |
b = 8.1303 (3) Å | µ = 0.33 mm−1 |
c = 11.5356 (6) Å | T = 120 K |
α = 84.032 (3)° | 0.18 × 0.16 × 0.03 mm |
β = 84.297 (2)° |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 2720 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick,. 2003) | 1943 reflections with I > 2σ(I) |
Tmin = 0.933, Tmax = 0.990 | Rint = 0.052 |
12303 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.26 e Å−3 |
2720 reflections | Δρmin = −0.29 e Å−3 |
163 parameters |
x | y | z | Uiso*/Ueq | ||
N11 | 0.7571 (3) | 0.9978 (2) | 0.48546 (15) | 0.0235 (4) | |
C12 | 0.7752 (3) | 0.9063 (3) | 0.58821 (17) | 0.0199 (4) | |
Cl1 | 0.78295 (8) | 1.02152 (7) | 0.70544 (5) | 0.02776 (17) | |
C13 | 0.7785 (3) | 0.7329 (2) | 0.60679 (17) | 0.0197 (4) | |
C14 | 0.7568 (3) | 0.6539 (3) | 0.50950 (18) | 0.0234 (5) | |
C15 | 0.7400 (3) | 0.7458 (3) | 0.40094 (18) | 0.0258 (5) | |
C16 | 0.7432 (3) | 0.9155 (3) | 0.39284 (19) | 0.0258 (5) | |
C17 | 0.8196 (3) | 0.6272 (3) | 0.72202 (17) | 0.0209 (4) | |
O1 | 0.9775 (2) | 0.61153 (18) | 0.77274 (12) | 0.0271 (4) | |
N21 | 0.6788 (3) | 0.5477 (2) | 0.75786 (14) | 0.0209 (4) | |
C21 | 0.6875 (3) | 0.4219 (2) | 0.85440 (17) | 0.0205 (4) | |
C22 | 0.5108 (3) | 0.3715 (3) | 0.87844 (18) | 0.0231 (5) | |
C23 | 0.5070 (4) | 0.2461 (3) | 0.96891 (18) | 0.0270 (5) | |
C24 | 0.6789 (4) | 0.1759 (3) | 1.03364 (18) | 0.0277 (5) | |
F24 | 0.6761 (2) | 0.05172 (17) | 1.12278 (11) | 0.0396 (4) | |
C25 | 0.8533 (4) | 0.2245 (3) | 1.01359 (19) | 0.0288 (5) | |
C26 | 0.8583 (3) | 0.3489 (3) | 0.92234 (19) | 0.0268 (5) | |
O2 | 0.3127 (2) | 0.65660 (18) | 0.63096 (13) | 0.0276 (4) | |
H14 | 0.7534 | 0.5374 | 0.5177 | 0.028* | |
H15 | 0.7267 | 0.6935 | 0.3336 | 0.031* | |
H16 | 0.7353 | 0.9775 | 0.3180 | 0.031* | |
H21 | 0.5606 | 0.5839 | 0.7159 | 0.025* | |
H22 | 0.3927 | 0.4232 | 0.8327 | 0.028* | |
H23 | 0.3880 | 0.2098 | 0.9855 | 0.032* | |
H25 | 0.9689 | 0.1740 | 1.0612 | 0.035* | |
H26 | 0.9784 | 0.3839 | 0.9066 | 0.032* | |
H2A | 0.2798 | 0.7599 | 0.5792 | 0.041* | |
H2B | 0.2058 | 0.6458 | 0.6689 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0174 (9) | 0.0273 (9) | 0.0255 (10) | −0.0077 (7) | −0.0038 (7) | 0.0021 (7) |
C12 | 0.0127 (10) | 0.0235 (10) | 0.0238 (11) | −0.0060 (8) | −0.0026 (8) | −0.0026 (8) |
Cl1 | 0.0311 (3) | 0.0269 (3) | 0.0277 (3) | −0.0113 (2) | −0.0042 (2) | −0.0056 (2) |
C13 | 0.0122 (10) | 0.0223 (10) | 0.0235 (11) | −0.0052 (8) | −0.0003 (8) | −0.0001 (8) |
C14 | 0.0182 (11) | 0.0239 (11) | 0.0277 (12) | −0.0062 (8) | −0.0033 (9) | −0.0027 (9) |
C15 | 0.0214 (11) | 0.0311 (12) | 0.0245 (12) | −0.0075 (9) | −0.0033 (9) | −0.0048 (9) |
C16 | 0.0199 (11) | 0.0321 (12) | 0.0229 (11) | −0.0068 (9) | −0.0020 (9) | 0.0027 (9) |
C17 | 0.0181 (11) | 0.0223 (10) | 0.0221 (11) | −0.0063 (8) | −0.0025 (8) | −0.0021 (8) |
O1 | 0.0237 (8) | 0.0326 (8) | 0.0279 (8) | −0.0134 (6) | −0.0084 (6) | 0.0044 (6) |
N21 | 0.0169 (9) | 0.0217 (9) | 0.0249 (10) | −0.0078 (7) | −0.0061 (7) | 0.0039 (7) |
C21 | 0.0226 (11) | 0.0171 (10) | 0.0211 (11) | −0.0057 (8) | −0.0015 (8) | −0.0026 (8) |
C22 | 0.0234 (11) | 0.0254 (11) | 0.0227 (11) | −0.0105 (9) | −0.0028 (9) | −0.0031 (8) |
C23 | 0.0325 (13) | 0.0292 (11) | 0.0240 (12) | −0.0168 (10) | −0.0002 (10) | −0.0033 (9) |
C24 | 0.0413 (14) | 0.0222 (11) | 0.0197 (11) | −0.0123 (10) | −0.0010 (10) | 0.0012 (8) |
F24 | 0.0566 (9) | 0.0359 (7) | 0.0300 (8) | −0.0230 (7) | −0.0073 (7) | 0.0111 (6) |
C25 | 0.0285 (12) | 0.0275 (12) | 0.0277 (12) | −0.0056 (9) | −0.0081 (10) | 0.0022 (9) |
C26 | 0.0233 (12) | 0.0271 (11) | 0.0297 (12) | −0.0086 (9) | −0.0046 (9) | 0.0016 (9) |
O2 | 0.0212 (8) | 0.0271 (8) | 0.0357 (9) | −0.0111 (6) | −0.0052 (6) | 0.0057 (6) |
N11—C12 | 1.325 (3) | N21—H21 | 0.9217 |
N11—C16 | 1.345 (3) | C21—C26 | 1.386 (3) |
C12—C13 | 1.397 (3) | C21—C22 | 1.394 (3) |
C12—Cl1 | 1.738 (2) | C22—C23 | 1.386 (3) |
C13—C14 | 1.394 (3) | C22—H22 | 0.95 |
C13—C17 | 1.501 (3) | C23—C24 | 1.368 (3) |
C14—C15 | 1.384 (3) | C23—H23 | 0.95 |
C14—H14 | 0.95 | C24—C25 | 1.367 (3) |
C15—C16 | 1.381 (3) | C24—F24 | 1.368 (2) |
C15—H15 | 0.95 | C25—C26 | 1.389 (3) |
C16—H16 | 0.95 | C25—H25 | 0.95 |
C17—O1 | 1.235 (2) | C26—H26 | 0.95 |
C17—N21 | 1.343 (2) | O2—H2A | 0.9508 |
N21—C21 | 1.423 (2) | O2—H2B | 0.8371 |
C12—N11—C16 | 117.01 (17) | C21—N21—H21 | 117.2 |
N11—C12—C13 | 124.72 (19) | C26—C21—C22 | 120.02 (19) |
N11—C12—Cl1 | 115.00 (15) | C26—C21—N21 | 123.98 (18) |
C13—C12—Cl1 | 120.21 (15) | C22—C21—N21 | 116.00 (18) |
C14—C13—C12 | 116.67 (18) | C23—C22—C21 | 120.2 (2) |
C14—C13—C17 | 119.78 (18) | C23—C22—H22 | 119.9 |
C12—C13—C17 | 123.38 (18) | C21—C22—H22 | 119.9 |
C15—C14—C13 | 119.74 (19) | C24—C23—C22 | 118.3 (2) |
C15—C14—H14 | 120.1 | C24—C23—H23 | 120.9 |
C13—C14—H14 | 120.1 | C22—C23—H23 | 120.9 |
C16—C15—C14 | 118.4 (2) | C25—C24—C23 | 123.1 (2) |
C16—C15—H15 | 120.8 | C25—C24—F24 | 118.5 (2) |
C14—C15—H15 | 120.8 | C23—C24—F24 | 118.43 (19) |
N11—C16—C15 | 123.42 (19) | C24—C25—C26 | 118.8 (2) |
N11—C16—H16 | 118.3 | C24—C25—H25 | 120.6 |
C15—C16—H16 | 118.3 | C26—C25—H25 | 120.6 |
O1—C17—N21 | 125.40 (18) | C21—C26—C25 | 119.7 (2) |
O1—C17—C13 | 120.50 (17) | C21—C26—H26 | 120.2 |
N21—C17—C13 | 113.99 (17) | C25—C26—H26 | 120.2 |
C17—N21—C21 | 127.79 (17) | H2A—O2—H2B | 112.3 |
C17—N21—H21 | 114.9 | ||
C16—N11—C12—C13 | −0.7 (3) | O1—C17—N21—C21 | −4.9 (3) |
C16—N11—C12—Cl1 | −177.79 (14) | C13—C17—N21—C21 | 171.39 (18) |
N11—C12—C13—C14 | −1.4 (3) | C17—N21—C21—C26 | −5.9 (3) |
Cl1—C12—C13—C14 | 175.56 (14) | C17—N21—C21—C22 | 174.60 (18) |
N11—C12—C13—C17 | 174.01 (18) | C26—C21—C22—C23 | −1.2 (3) |
Cl1—C12—C13—C17 | −9.1 (3) | N21—C21—C22—C23 | 178.30 (17) |
C12—C13—C14—C15 | 2.0 (3) | C21—C22—C23—C24 | 0.7 (3) |
C17—C13—C14—C15 | −173.52 (18) | C22—C23—C24—C25 | 0.4 (3) |
C13—C14—C15—C16 | −0.7 (3) | C22—C23—C24—F24 | −179.80 (18) |
C12—N11—C16—C15 | 2.2 (3) | C23—C24—C25—C26 | −1.0 (3) |
C14—C15—C16—N11 | −1.5 (3) | F24—C24—C25—C26 | 179.21 (18) |
C14—C13—C17—O1 | 122.2 (2) | C22—C21—C26—C25 | 0.6 (3) |
C12—C13—C17—O1 | −53.0 (3) | N21—C21—C26—C25 | −178.85 (19) |
C14—C13—C17—N21 | −54.2 (2) | C24—C25—C26—C21 | 0.5 (3) |
C12—C13—C17—N21 | 130.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···N11i | 0.95 | 1.97 | 2.887 (2) | 161 |
O2—H2B···O1ii | 0.84 | 1.95 | 2.780 (2) | 173 |
N21—H21···O2 | 0.92 | 1.91 | 2.837 (2) | 179 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y, z. |
C12H8Cl2N2O | F(000) = 1088 |
Mr = 267.10 | Dx = 1.543 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 9787 reflections |
a = 5.0855 (8) Å | θ = 3.0–27.5° |
b = 28.982 (8) Å | µ = 0.55 mm−1 |
c = 15.607 (4) Å | T = 120 K |
β = 90.37 (2)° | Plate, colourless |
V = 2300.2 (9) Å3 | 0.28 × 0.07 × 0.03 mm |
Z = 8 |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 9787 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 6370 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ϕ & ω scans | h = −6→6 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −37→37 |
Tmin = 0.862, Tmax = 0.984 | l = −20→20 |
24726 measured reflections |
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)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.169 | w = 1/[σ2(Fo2) + (0.0454P)2 + 5.774P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
9787 reflections | Δρmax = 0.79 e Å−3 |
254 parameters | Δρmin = −0.54 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 4396 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.54 (11) |
C12H8Cl2N2O | V = 2300.2 (9) Å3 |
Mr = 267.10 | Z = 8 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.0855 (8) Å | µ = 0.55 mm−1 |
b = 28.982 (8) Å | T = 120 K |
c = 15.607 (4) Å | 0.28 × 0.07 × 0.03 mm |
β = 90.37 (2)° |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 9787 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 6370 reflections with I > 2σ(I) |
Tmin = 0.862, Tmax = 0.984 | Rint = 0.053 |
24726 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | H-atom parameters constrained |
wR(F2) = 0.169 | Δρmax = 0.79 e Å−3 |
S = 1.04 | Δρmin = −0.54 e Å−3 |
9787 reflections | Absolute structure: Flack (1983), 4396 Friedel pairs |
254 parameters | Absolute structure parameter: 0.54 (11) |
1 restraint |
x | y | z | Uiso*/Ueq | ||
N11 | 1.0930 (11) | −0.1416 (2) | −0.0684 (4) | 0.0249 (6) | |
C12 | 1.1545 (15) | −0.0970 (3) | −0.0642 (5) | 0.0249 (6) | |
Cl1 | 1.3934 (4) | −0.07776 (6) | −0.13183 (11) | 0.0255 (4) | |
C13 | 1.0218 (16) | −0.0653 (3) | −0.0091 (5) | 0.0249 (6) | |
C14 | 0.8354 (15) | −0.0820 (3) | 0.0465 (4) | 0.0249 (6) | |
C15 | 0.7658 (14) | −0.1313 (3) | 0.0424 (5) | 0.0249 (6) | |
C16 | 0.8947 (12) | −0.1561 (3) | −0.0104 (4) | 0.0249 (6) | |
C17 | 1.0824 (14) | −0.0137 (3) | −0.0081 (5) | 0.0249 (6) | |
O1 | 1.3151 (10) | −0.00037 (17) | −0.0012 (3) | 0.0249 (6) | |
N21 | 0.8848 (12) | 0.0131 (2) | −0.0071 (4) | 0.0193 (5) | |
Cl24 | 0.8822 (4) | 0.21692 (6) | 0.02990 (14) | 0.0324 (5) | |
C21 | 0.8859 (7) | 0.06241 (12) | 0.0004 (2) | 0.0193 (5) | |
C22 | 0.6884 (6) | 0.08819 (14) | −0.0387 (2) | 0.0193 (5) | |
C23 | 0.6872 (6) | 0.13596 (14) | −0.0308 (2) | 0.0193 (5) | |
C24 | 0.8835 (7) | 0.15795 (12) | 0.0162 (2) | 0.0193 (5) | |
C25 | 1.0810 (6) | 0.13216 (14) | 0.0554 (2) | 0.0193 (5) | |
C26 | 1.0822 (6) | 0.08439 (14) | 0.0474 (2) | 0.0193 (5) | |
N31 | 0.3668 (10) | 0.8114 (2) | 0.1869 (4) | 0.0231 (5) | |
C32 | 0.4029 (15) | 0.7668 (3) | 0.1884 (5) | 0.0231 (5) | |
Cl3 | 0.6478 (4) | 0.74925 (6) | 0.11518 (12) | 0.0285 (5) | |
C33 | 0.2773 (16) | 0.7352 (3) | 0.2393 (5) | 0.0231 (5) | |
C34 | 0.0798 (15) | 0.7547 (3) | 0.2904 (5) | 0.0231 (5) | |
C35 | 0.0404 (13) | 0.7987 (2) | 0.2935 (5) | 0.0231 (5) | |
C36 | 0.1852 (12) | 0.8288 (2) | 0.2357 (4) | 0.0231 (5) | |
C37 | 0.3454 (14) | 0.6860 (3) | 0.2416 (5) | 0.0231 (5) | |
O3 | 0.5701 (9) | 0.67153 (16) | 0.2390 (3) | 0.0231 (5) | |
N41 | 0.1203 (12) | 0.6564 (2) | 0.2434 (4) | 0.0211 (5) | |
Cl44 | 0.1270 (4) | 0.45328 (6) | 0.27721 (12) | 0.0280 (5) | |
C41 | 0.1364 (7) | 0.60846 (12) | 0.2500 (2) | 0.0211 (5) | |
C42 | −0.0605 (6) | 0.58283 (15) | 0.2102 (2) | 0.0211 (5) | |
C43 | −0.0640 (6) | 0.53508 (14) | 0.2184 (2) | 0.0211 (5) | |
C44 | 0.1295 (7) | 0.51296 (12) | 0.2665 (3) | 0.0211 (5) | |
C45 | 0.3263 (6) | 0.53858 (14) | 0.3063 (2) | 0.0211 (5) | |
C46 | 0.3298 (6) | 0.58633 (14) | 0.2981 (2) | 0.0211 (5) | |
N51 | 0.4263 (11) | 0.3580 (2) | 0.5740 (4) | 0.0252 (6) | |
C52 | 0.3620 (15) | 0.4025 (3) | 0.5697 (5) | 0.0252 (6) | |
Cl5 | 0.1300 (4) | 0.42136 (6) | 0.64060 (11) | 0.0272 (4) | |
C53 | 0.4881 (16) | 0.4344 (3) | 0.5147 (5) | 0.0252 (6) | |
C54 | 0.6738 (15) | 0.4183 (3) | 0.4579 (5) | 0.0252 (6) | |
C55 | 0.7478 (13) | 0.3695 (2) | 0.4609 (5) | 0.0252 (6) | |
C56 | 0.6201 (12) | 0.3440 (3) | 0.5145 (4) | 0.0252 (6) | |
C57 | 0.4242 (14) | 0.4860 (3) | 0.5140 (5) | 0.0252 (6) | |
O5 | 0.1900 (10) | 0.49896 (17) | 0.5091 (3) | 0.0252 (6) | |
Cl64 | 0.5855 (4) | 0.71624 (6) | 0.46495 (13) | 0.0298 (5) | |
N61 | 0.6203 (12) | 0.5126 (2) | 0.5135 (4) | 0.0201 (5) | |
C61 | 0.6177 (7) | 0.56264 (12) | 0.5049 (2) | 0.0201 (5) | |
C62 | 0.8107 (6) | 0.58460 (14) | 0.4572 (2) | 0.0201 (5) | |
C63 | 0.8043 (6) | 0.63223 (15) | 0.4470 (2) | 0.0201 (5) | |
C64 | 0.6049 (7) | 0.65791 (12) | 0.4845 (2) | 0.0201 (5) | |
C65 | 0.4120 (6) | 0.63595 (15) | 0.5322 (2) | 0.0201 (5) | |
C66 | 0.4184 (6) | 0.58832 (15) | 0.5424 (2) | 0.0201 (5) | |
N71 | 1.1553 (11) | 0.3130 (2) | 0.3173 (4) | 0.0249 (6) | |
C72 | 1.1159 (15) | 0.2685 (3) | 0.3159 (5) | 0.0249 (6) | |
Cl7 | 0.8784 (4) | 0.25131 (6) | 0.39206 (12) | 0.0293 (5) | |
C73 | 1.2365 (16) | 0.2368 (3) | 0.2649 (5) | 0.0249 (6) | |
C74 | 1.4280 (15) | 0.2551 (3) | 0.2109 (5) | 0.0249 (6) | |
C75 | 1.4668 (13) | 0.2994 (2) | 0.2065 (5) | 0.0249 (6) | |
C76 | 1.3311 (12) | 0.3301 (2) | 0.2677 (4) | 0.0249 (6) | |
C77 | 1.1627 (14) | 0.1876 (3) | 0.2631 (5) | 0.0249 (6) | |
O7 | 0.9370 (9) | 0.17332 (16) | 0.2669 (3) | 0.0249 (6) | |
N81 | 1.3862 (12) | 0.1571 (2) | 0.2606 (4) | 0.0208 (5) | |
Cl84 | 1.3420 (4) | −0.04497 (6) | 0.21810 (13) | 0.0297 (5) | |
C81 | 1.3679 (7) | 0.10957 (12) | 0.2546 (2) | 0.0208 (5) | |
C82 | 1.5613 (6) | 0.08769 (14) | 0.2070 (2) | 0.0208 (5) | |
C83 | 1.5558 (6) | 0.04005 (14) | 0.1969 (2) | 0.0208 (5) | |
C84 | 1.3569 (7) | 0.01429 (12) | 0.2344 (3) | 0.0208 (5) | |
C85 | 1.1634 (6) | 0.03616 (15) | 0.2820 (2) | 0.0208 (5) | |
C86 | 1.1690 (6) | 0.08381 (15) | 0.2921 (2) | 0.0208 (5) | |
H14 | 0.7533 | −0.0621 | 0.0866 | 0.030* | |
H15 | 0.6315 | −0.1440 | 0.0772 | 0.030* | |
H16 | 0.8533 | −0.1881 | −0.0109 | 0.030* | |
H21 | 0.7294 | −0.0001 | −0.0116 | 0.023* | |
H22 | 0.5542 | 0.0732 | −0.0709 | 0.023* | |
H23 | 0.5522 | 0.1536 | −0.0575 | 0.023* | |
H25 | 1.2152 | 0.1472 | 0.0875 | 0.023* | |
H26 | 1.2172 | 0.0668 | 0.0742 | 0.023* | |
H34 | −0.0280 | 0.7349 | 0.3236 | 0.028* | |
H35 | −0.0815 | 0.8113 | 0.3330 | 0.028* | |
H36 | 0.1473 | 0.8608 | 0.2337 | 0.028* | |
H41 | −0.0366 | 0.6690 | 0.2401 | 0.025* | |
H42 | −0.1927 | 0.5980 | 0.1773 | 0.025* | |
H43 | −0.1985 | 0.5176 | 0.1912 | 0.025* | |
H45 | 0.4585 | 0.5235 | 0.3392 | 0.025* | |
H46 | 0.4644 | 0.6038 | 0.3253 | 0.025* | |
H54 | 0.7521 | 0.4385 | 0.4176 | 0.030* | |
H55 | 0.8820 | 0.3573 | 0.4255 | 0.030* | |
H56 | 0.6612 | 0.3121 | 0.5140 | 0.030* | |
H61 | 0.7756 | 0.4995 | 0.5189 | 0.024* | |
H62 | 0.9469 | 0.5670 | 0.4315 | 0.024* | |
H63 | 0.9362 | 0.6472 | 0.4144 | 0.024* | |
H65 | 0.2757 | 0.6535 | 0.5579 | 0.024* | |
H66 | 0.2865 | 0.5733 | 0.5750 | 0.024* | |
H74 | 1.5312 | 0.2349 | 0.1769 | 0.030* | |
H75 | 1.5809 | 0.3119 | 0.1646 | 0.030* | |
H76 | 1.3733 | 0.3620 | 0.2703 | 0.030* | |
H81 | 1.5441 | 0.1695 | 0.2629 | 0.025* | |
H82 | 1.6973 | 0.1053 | 0.1813 | 0.025* | |
H83 | 1.6880 | 0.0251 | 0.1643 | 0.025* | |
H85 | 1.0275 | 0.0186 | 0.3077 | 0.025* | |
H86 | 1.0368 | 0.0988 | 0.3247 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0242 (13) | 0.0245 (15) | 0.0262 (12) | −0.0006 (11) | 0.0013 (10) | −0.0009 (11) |
C12 | 0.0242 (13) | 0.0245 (15) | 0.0262 (12) | −0.0006 (11) | 0.0013 (10) | −0.0009 (11) |
Cl1 | 0.0312 (10) | 0.0205 (10) | 0.0249 (9) | 0.0036 (8) | 0.0083 (7) | 0.0004 (8) |
C13 | 0.0242 (13) | 0.0245 (15) | 0.0262 (12) | −0.0006 (11) | 0.0013 (10) | −0.0009 (11) |
C14 | 0.0242 (13) | 0.0245 (15) | 0.0262 (12) | −0.0006 (11) | 0.0013 (10) | −0.0009 (11) |
C15 | 0.0242 (13) | 0.0245 (15) | 0.0262 (12) | −0.0006 (11) | 0.0013 (10) | −0.0009 (11) |
C16 | 0.0242 (13) | 0.0245 (15) | 0.0262 (12) | −0.0006 (11) | 0.0013 (10) | −0.0009 (11) |
C17 | 0.0242 (13) | 0.0245 (15) | 0.0262 (12) | −0.0006 (11) | 0.0013 (10) | −0.0009 (11) |
O1 | 0.0242 (13) | 0.0245 (15) | 0.0262 (12) | −0.0006 (11) | 0.0013 (10) | −0.0009 (11) |
N21 | 0.0169 (11) | 0.0209 (12) | 0.0202 (12) | −0.0001 (10) | 0.0027 (9) | 0.0005 (9) |
Cl24 | 0.0369 (12) | 0.0165 (11) | 0.0438 (12) | −0.0031 (9) | 0.0072 (9) | 0.0017 (9) |
C21 | 0.0169 (11) | 0.0209 (12) | 0.0202 (12) | −0.0001 (10) | 0.0027 (9) | 0.0005 (9) |
C22 | 0.0169 (11) | 0.0209 (12) | 0.0202 (12) | −0.0001 (10) | 0.0027 (9) | 0.0005 (9) |
C23 | 0.0169 (11) | 0.0209 (12) | 0.0202 (12) | −0.0001 (10) | 0.0027 (9) | 0.0005 (9) |
C24 | 0.0169 (11) | 0.0209 (12) | 0.0202 (12) | −0.0001 (10) | 0.0027 (9) | 0.0005 (9) |
C25 | 0.0169 (11) | 0.0209 (12) | 0.0202 (12) | −0.0001 (10) | 0.0027 (9) | 0.0005 (9) |
C26 | 0.0169 (11) | 0.0209 (12) | 0.0202 (12) | −0.0001 (10) | 0.0027 (9) | 0.0005 (9) |
N31 | 0.0225 (12) | 0.0146 (12) | 0.0324 (13) | 0.0002 (10) | 0.0059 (10) | −0.0015 (10) |
C32 | 0.0225 (12) | 0.0146 (12) | 0.0324 (13) | 0.0002 (10) | 0.0059 (10) | −0.0015 (10) |
Cl3 | 0.0264 (10) | 0.0245 (11) | 0.0347 (11) | −0.0019 (9) | 0.0116 (8) | −0.0006 (9) |
C33 | 0.0225 (12) | 0.0146 (12) | 0.0324 (13) | 0.0002 (10) | 0.0059 (10) | −0.0015 (10) |
C34 | 0.0225 (12) | 0.0146 (12) | 0.0324 (13) | 0.0002 (10) | 0.0059 (10) | −0.0015 (10) |
C35 | 0.0225 (12) | 0.0146 (12) | 0.0324 (13) | 0.0002 (10) | 0.0059 (10) | −0.0015 (10) |
C36 | 0.0225 (12) | 0.0146 (12) | 0.0324 (13) | 0.0002 (10) | 0.0059 (10) | −0.0015 (10) |
C37 | 0.0225 (12) | 0.0146 (12) | 0.0324 (13) | 0.0002 (10) | 0.0059 (10) | −0.0015 (10) |
O3 | 0.0225 (12) | 0.0146 (12) | 0.0324 (13) | 0.0002 (10) | 0.0059 (10) | −0.0015 (10) |
N41 | 0.0228 (12) | 0.0173 (12) | 0.0233 (12) | 0.0005 (10) | 0.0042 (9) | −0.0003 (10) |
Cl44 | 0.0373 (12) | 0.0153 (10) | 0.0314 (10) | −0.0023 (8) | 0.0044 (8) | 0.0018 (8) |
C41 | 0.0228 (12) | 0.0173 (12) | 0.0233 (12) | 0.0005 (10) | 0.0042 (9) | −0.0003 (10) |
C42 | 0.0228 (12) | 0.0173 (12) | 0.0233 (12) | 0.0005 (10) | 0.0042 (9) | −0.0003 (10) |
C43 | 0.0228 (12) | 0.0173 (12) | 0.0233 (12) | 0.0005 (10) | 0.0042 (9) | −0.0003 (10) |
C44 | 0.0228 (12) | 0.0173 (12) | 0.0233 (12) | 0.0005 (10) | 0.0042 (9) | −0.0003 (10) |
C45 | 0.0228 (12) | 0.0173 (12) | 0.0233 (12) | 0.0005 (10) | 0.0042 (9) | −0.0003 (10) |
C46 | 0.0228 (12) | 0.0173 (12) | 0.0233 (12) | 0.0005 (10) | 0.0042 (9) | −0.0003 (10) |
N51 | 0.0209 (13) | 0.0243 (15) | 0.0304 (13) | 0.0018 (10) | −0.0007 (10) | 0.0006 (11) |
C52 | 0.0209 (13) | 0.0243 (15) | 0.0304 (13) | 0.0018 (10) | −0.0007 (10) | 0.0006 (11) |
Cl5 | 0.0313 (10) | 0.0197 (10) | 0.0308 (10) | −0.0008 (9) | 0.0123 (8) | 0.0001 (9) |
C53 | 0.0209 (13) | 0.0243 (15) | 0.0304 (13) | 0.0018 (10) | −0.0007 (10) | 0.0006 (11) |
C54 | 0.0209 (13) | 0.0243 (15) | 0.0304 (13) | 0.0018 (10) | −0.0007 (10) | 0.0006 (11) |
C55 | 0.0209 (13) | 0.0243 (15) | 0.0304 (13) | 0.0018 (10) | −0.0007 (10) | 0.0006 (11) |
C56 | 0.0209 (13) | 0.0243 (15) | 0.0304 (13) | 0.0018 (10) | −0.0007 (10) | 0.0006 (11) |
C57 | 0.0209 (13) | 0.0243 (15) | 0.0304 (13) | 0.0018 (10) | −0.0007 (10) | 0.0006 (11) |
O5 | 0.0209 (13) | 0.0243 (15) | 0.0304 (13) | 0.0018 (10) | −0.0007 (10) | 0.0006 (11) |
Cl64 | 0.0330 (11) | 0.0164 (10) | 0.0400 (11) | 0.0020 (8) | 0.0040 (9) | −0.0033 (8) |
N61 | 0.0169 (11) | 0.0228 (13) | 0.0207 (12) | 0.0021 (10) | 0.0004 (9) | −0.0001 (10) |
C61 | 0.0169 (11) | 0.0228 (13) | 0.0207 (12) | 0.0021 (10) | 0.0004 (9) | −0.0001 (10) |
C62 | 0.0169 (11) | 0.0228 (13) | 0.0207 (12) | 0.0021 (10) | 0.0004 (9) | −0.0001 (10) |
C63 | 0.0169 (11) | 0.0228 (13) | 0.0207 (12) | 0.0021 (10) | 0.0004 (9) | −0.0001 (10) |
C64 | 0.0169 (11) | 0.0228 (13) | 0.0207 (12) | 0.0021 (10) | 0.0004 (9) | −0.0001 (10) |
C65 | 0.0169 (11) | 0.0228 (13) | 0.0207 (12) | 0.0021 (10) | 0.0004 (9) | −0.0001 (10) |
C66 | 0.0169 (11) | 0.0228 (13) | 0.0207 (12) | 0.0021 (10) | 0.0004 (9) | −0.0001 (10) |
N71 | 0.0249 (13) | 0.0151 (13) | 0.0347 (13) | −0.0005 (10) | 0.0085 (10) | −0.0005 (10) |
C72 | 0.0249 (13) | 0.0151 (13) | 0.0347 (13) | −0.0005 (10) | 0.0085 (10) | −0.0005 (10) |
Cl7 | 0.0345 (11) | 0.0208 (10) | 0.0328 (10) | −0.0023 (9) | 0.0145 (8) | −0.0038 (8) |
C73 | 0.0249 (13) | 0.0151 (13) | 0.0347 (13) | −0.0005 (10) | 0.0085 (10) | −0.0005 (10) |
C74 | 0.0249 (13) | 0.0151 (13) | 0.0347 (13) | −0.0005 (10) | 0.0085 (10) | −0.0005 (10) |
C75 | 0.0249 (13) | 0.0151 (13) | 0.0347 (13) | −0.0005 (10) | 0.0085 (10) | −0.0005 (10) |
C76 | 0.0249 (13) | 0.0151 (13) | 0.0347 (13) | −0.0005 (10) | 0.0085 (10) | −0.0005 (10) |
C77 | 0.0249 (13) | 0.0151 (13) | 0.0347 (13) | −0.0005 (10) | 0.0085 (10) | −0.0005 (10) |
O7 | 0.0249 (13) | 0.0151 (13) | 0.0347 (13) | −0.0005 (10) | 0.0085 (10) | −0.0005 (10) |
N81 | 0.0216 (12) | 0.0169 (12) | 0.0239 (12) | −0.0014 (10) | −0.0002 (9) | 0.0019 (9) |
Cl84 | 0.0394 (12) | 0.0163 (10) | 0.0335 (10) | −0.0024 (9) | 0.0101 (9) | −0.0031 (8) |
C81 | 0.0216 (12) | 0.0169 (12) | 0.0239 (12) | −0.0014 (10) | −0.0002 (9) | 0.0019 (9) |
C82 | 0.0216 (12) | 0.0169 (12) | 0.0239 (12) | −0.0014 (10) | −0.0002 (9) | 0.0019 (9) |
C83 | 0.0216 (12) | 0.0169 (12) | 0.0239 (12) | −0.0014 (10) | −0.0002 (9) | 0.0019 (9) |
C84 | 0.0216 (12) | 0.0169 (12) | 0.0239 (12) | −0.0014 (10) | −0.0002 (9) | 0.0019 (9) |
C85 | 0.0216 (12) | 0.0169 (12) | 0.0239 (12) | −0.0014 (10) | −0.0002 (9) | 0.0019 (9) |
C86 | 0.0216 (12) | 0.0169 (12) | 0.0239 (12) | −0.0014 (10) | −0.0002 (9) | 0.0019 (9) |
N11—C12 | 1.330 (10) | N51—C52 | 1.330 (10) |
N11—C16 | 1.424 (9) | N51—C56 | 1.418 (9) |
C12—C13 | 1.432 (12) | C52—C53 | 1.418 (12) |
C12—Cl1 | 1.709 (8) | C52—Cl5 | 1.713 (8) |
C13—C14 | 1.376 (11) | C53—C54 | 1.382 (11) |
C13—C17 | 1.525 (11) | C53—C57 | 1.530 (11) |
C14—C15 | 1.474 (11) | C54—C55 | 1.462 (11) |
C14—H14 | 0.95 | C54—H54 | 0.95 |
C15—C16 | 1.278 (10) | C55—C56 | 1.295 (10) |
C15—H15 | 0.95 | C55—H55 | 0.95 |
C16—H16 | 0.95 | C56—H56 | 0.95 |
C17—O1 | 1.249 (9) | C57—O5 | 1.251 (9) |
C17—N21 | 1.270 (9) | C57—N61 | 1.260 (9) |
N21—C21 | 1.435 (7) | Cl64—C64 | 1.721 (4) |
N21—H21 | 0.88 | N61—C61 | 1.456 (7) |
Cl24—C24 | 1.722 (4) | N61—H61 | 0.88 |
C21—C22 | 1.39 | C61—C62 | 1.39 |
C21—C26 | 1.39 | C61—C66 | 1.39 |
C22—C23 | 1.39 | C62—C63 | 1.39 |
C22—H22 | 0.95 | C62—H62 | 0.95 |
C23—C24 | 1.39 | C63—C64 | 1.39 |
C23—H23 | 0.95 | C63—H63 | 0.95 |
C24—C25 | 1.39 | C64—C65 | 1.39 |
C25—C26 | 1.39 | C65—C66 | 1.39 |
C25—H25 | 0.95 | C65—H65 | 0.95 |
C26—H26 | 0.95 | C66—H66 | 0.95 |
N31—C36 | 1.302 (8) | N71—C76 | 1.285 (9) |
N31—C32 | 1.307 (10) | N71—C72 | 1.305 (10) |
C32—C33 | 1.372 (11) | C72—C73 | 1.365 (11) |
C32—Cl3 | 1.770 (8) | C72—Cl7 | 1.771 (8) |
C33—C34 | 1.405 (11) | C73—C74 | 1.396 (11) |
C33—C37 | 1.469 (10) | C73—C77 | 1.474 (11) |
C34—C35 | 1.290 (11) | C74—C75 | 1.300 (11) |
C34—H34 | 0.95 | C74—H74 | 0.95 |
C35—C36 | 1.458 (9) | C75—C76 | 1.479 (10) |
C35—H35 | 0.95 | C75—H75 | 0.95 |
C36—H36 | 0.95 | C76—H76 | 0.95 |
C37—O3 | 1.218 (8) | C77—O7 | 1.222 (8) |
C37—N41 | 1.431 (9) | C77—N81 | 1.441 (9) |
N41—C41 | 1.394 (7) | N81—C81 | 1.384 (7) |
N41—H41 | 0.88 | N81—H81 | 0.88 |
Cl44—C44 | 1.738 (4) | Cl84—C84 | 1.738 (4) |
C41—C42 | 1.39 | C81—C82 | 1.39 |
C41—C46 | 1.39 | C81—C86 | 1.39 |
C42—C43 | 1.39 | C82—C83 | 1.39 |
C42—H42 | 0.95 | C82—H82 | 0.95 |
C43—C44 | 1.39 | C83—C84 | 1.39 |
C43—H43 | 0.95 | C83—H83 | 0.95 |
C44—C45 | 1.39 | C84—C85 | 1.39 |
C45—C46 | 1.39 | C85—C86 | 1.39 |
C45—H45 | 0.95 | C85—H85 | 0.95 |
C46—H46 | 0.95 | C86—H86 | 0.95 |
C12—N11—C16 | 115.0 (6) | C52—N51—C56 | 114.5 (6) |
N11—C12—C13 | 122.9 (7) | N51—C52—C53 | 123.4 (7) |
N11—C12—Cl1 | 117.0 (6) | N51—C52—Cl5 | 116.5 (6) |
C13—C12—Cl1 | 120.0 (6) | C53—C52—Cl5 | 119.9 (6) |
C14—C13—C12 | 118.8 (8) | C54—C53—C52 | 118.7 (8) |
C14—C13—C17 | 118.5 (7) | C54—C53—C57 | 118.2 (7) |
C12—C13—C17 | 122.7 (7) | C52—C53—C57 | 123.1 (7) |
C13—C14—C15 | 118.7 (7) | C53—C54—C55 | 118.9 (7) |
C13—C14—H14 | 120.7 | C53—C54—H54 | 120.5 |
C15—C14—H14 | 120.7 | C55—C54—H54 | 120.5 |
C16—C15—C14 | 116.8 (7) | C56—C55—C54 | 116.2 (7) |
C16—C15—H15 | 121.6 | C56—C55—H55 | 121.9 |
C14—C15—H15 | 121.6 | C54—C55—H55 | 121.9 |
C15—C16—N11 | 127.7 (7) | C55—C56—N51 | 127.9 (7) |
C15—C16—H16 | 116.2 | C55—C56—H56 | 116.1 |
N11—C16—H16 | 116.2 | N51—C56—H56 | 116.1 |
O1—C17—N21 | 124.0 (8) | O5—C57—N61 | 124.7 (8) |
O1—C17—C13 | 119.7 (7) | O5—C57—C53 | 119.7 (7) |
N21—C17—C13 | 116.0 (7) | N61—C57—C53 | 115.4 (7) |
C17—N21—C21 | 127.4 (6) | C57—N61—C61 | 127.1 (6) |
C17—N21—H21 | 116.3 | C57—N61—H61 | 116.5 |
C21—N21—H21 | 116.3 | C61—N61—H61 | 116.5 |
C22—C21—C26 | 120.0 | C62—C61—C66 | 120.0 |
C22—C21—N21 | 119.8 (3) | C62—C61—N61 | 120.0 (3) |
C26—C21—N21 | 120.2 (3) | C66—C61—N61 | 120.0 (3) |
C21—C22—C23 | 120.0 | C61—C62—C63 | 120.0 |
C21—C22—H22 | 120.0 | C61—C62—H62 | 120.0 |
C23—C22—H22 | 120.0 | C63—C62—H62 | 120.0 |
C24—C23—C22 | 120.0 | C64—C63—C62 | 120.0 |
C24—C23—H23 | 120.0 | C64—C63—H63 | 120.0 |
C22—C23—H23 | 120.0 | C62—C63—H63 | 120.0 |
C25—C24—C23 | 120.0 | C65—C64—C63 | 120.0 |
C25—C24—Cl24 | 118.8 (2) | C65—C64—Cl64 | 120.3 (2) |
C23—C24—Cl24 | 121.1 (2) | C63—C64—Cl64 | 119.5 (2) |
C24—C25—C26 | 120.0 | C66—C65—C64 | 120.0 |
C24—C25—H25 | 120.0 | C66—C65—H65 | 120.0 |
C26—C25—H25 | 120.0 | C64—C65—H65 | 120.0 |
C25—C26—C21 | 120.0 | C65—C66—C61 | 120.0 |
C25—C26—H26 | 120.0 | C65—C66—H66 | 120.0 |
C21—C26—H26 | 120.0 | C61—C66—H66 | 120.0 |
C36—N31—C32 | 118.2 (6) | C76—N71—C72 | 118.6 (7) |
N31—C32—C33 | 127.1 (7) | N71—C72—C73 | 127.2 (8) |
N31—C32—Cl3 | 111.9 (6) | N71—C72—Cl7 | 111.9 (6) |
C33—C32—Cl3 | 121.0 (6) | C73—C72—Cl7 | 120.9 (6) |
C32—C33—C34 | 113.4 (7) | C72—C73—C74 | 114.5 (7) |
C32—C33—C37 | 123.5 (7) | C72—C73—C77 | 123.1 (7) |
C34—C33—C37 | 123.1 (7) | C74—C73—C77 | 122.3 (7) |
C35—C34—C33 | 122.0 (8) | C75—C74—C73 | 120.8 (8) |
C35—C34—H34 | 119.0 | C75—C74—H74 | 119.6 |
C33—C34—H34 | 119.0 | C73—C74—H74 | 119.6 |
C34—C35—C36 | 119.2 (7) | C74—C75—C76 | 119.3 (7) |
C34—C35—H35 | 120.4 | C74—C75—H75 | 120.4 |
C36—C35—H35 | 120.4 | C76—C75—H75 | 120.4 |
N31—C36—C35 | 119.6 (6) | N71—C76—C75 | 119.0 (6) |
N31—C36—H36 | 120.2 | N71—C76—H76 | 120.5 |
C35—C36—H36 | 120.2 | C75—C76—H76 | 120.5 |
O3—C37—N41 | 123.0 (7) | O7—C77—N81 | 122.3 (7) |
O3—C37—C33 | 123.6 (7) | O7—C77—C73 | 124.5 (7) |
N41—C37—C33 | 113.3 (6) | N81—C77—C73 | 113.1 (6) |
C41—N41—C37 | 123.5 (6) | C81—N81—C77 | 124.1 (6) |
C41—N41—H41 | 118.2 | C81—N81—H81 | 118.0 |
C37—N41—H41 | 118.2 | C77—N81—H81 | 118.0 |
C42—C41—C46 | 120.0 | N81—C81—C82 | 116.3 (3) |
C42—C41—N41 | 117.2 (3) | N81—C81—C86 | 123.7 (3) |
C46—C41—N41 | 122.7 (3) | C82—C81—C86 | 120.0 |
C43—C42—C41 | 120.0 | C81—C82—C83 | 120.0 |
C43—C42—H42 | 120.0 | C81—C82—H82 | 120.0 |
C41—C42—H42 | 120.0 | C83—C82—H82 | 120.0 |
C42—C43—C44 | 120.0 | C84—C83—C82 | 120.0 |
C42—C43—H43 | 120.0 | C84—C83—H83 | 120.0 |
C44—C43—H43 | 120.0 | C82—C83—H83 | 120.0 |
C45—C44—C43 | 120.0 | C83—C84—C85 | 120.0 |
C45—C44—Cl44 | 119.6 (2) | C83—C84—Cl84 | 120.0 (2) |
C43—C44—Cl44 | 120.4 (2) | C85—C84—Cl84 | 119.9 (2) |
C44—C45—C46 | 120.0 | C84—C85—C86 | 120.0 |
C44—C45—H45 | 120.0 | C84—C85—H85 | 120.0 |
C46—C45—H45 | 120.0 | C86—C85—H85 | 120.0 |
C45—C46—C41 | 120.0 | C85—C86—C81 | 120.0 |
C45—C46—H46 | 120.0 | C85—C86—H86 | 120.0 |
C41—C46—H46 | 120.0 | C81—C86—H86 | 120.0 |
C16—N11—C12—C13 | −3.4 (10) | C56—N51—C52—C53 | −4.3 (10) |
C16—N11—C12—Cl1 | 179.5 (5) | C56—N51—C52—Cl5 | −179.6 (5) |
N11—C12—C13—C14 | 4.8 (11) | N51—C52—C53—C54 | 5.1 (12) |
Cl1—C12—C13—C14 | −178.2 (5) | Cl5—C52—C53—C54 | −179.8 (6) |
N11—C12—C13—C17 | −176.5 (7) | N51—C52—C53—C57 | −176.2 (6) |
Cl1—C12—C13—C17 | 0.5 (10) | Cl5—C52—C53—C57 | −1.1 (10) |
C12—C13—C14—C15 | −4.6 (10) | C52—C53—C54—C55 | −4.6 (11) |
C17—C13—C14—C15 | 176.7 (6) | C57—C53—C54—C55 | 176.7 (6) |
C13—C14—C15—C16 | 3.5 (10) | C53—C54—C55—C56 | 3.9 (10) |
C14—C15—C16—N11 | −2.4 (10) | C54—C55—C56—N51 | −3.6 (10) |
C12—N11—C16—C15 | 2.5 (10) | C52—N51—C56—C55 | 3.8 (10) |
C14—C13—C17—O1 | 128.4 (8) | C54—C53—C57—O5 | 129.1 (8) |
C12—C13—C17—O1 | −50.3 (10) | C52—C53—C57—O5 | −49.6 (11) |
C14—C13—C17—N21 | −45.8 (9) | C54—C53—C57—N61 | −46.9 (10) |
C12—C13—C17—N21 | 135.5 (8) | C52—C53—C57—N61 | 134.4 (8) |
O1—C17—N21—C21 | 1.0 (12) | O5—C57—N61—C61 | −1.8 (12) |
C13—C17—N21—C21 | 175.0 (6) | C53—C57—N61—C61 | 173.9 (6) |
C17—N21—C21—C22 | 149.0 (6) | C57—N61—C61—C62 | −141.9 (6) |
C17—N21—C21—C26 | −31.7 (8) | C57—N61—C61—C66 | 36.4 (8) |
C26—C21—C22—C23 | 0.0 | C66—C61—C62—C63 | 0.0 |
N21—C21—C22—C23 | 179.3 (4) | N61—C61—C62—C63 | 178.2 (4) |
C21—C22—C23—C24 | 0.0 | C61—C62—C63—C64 | 0.0 |
C22—C23—C24—C25 | 0.0 | C62—C63—C64—C65 | 0.0 |
C22—C23—C24—Cl24 | −178.1 (3) | C62—C63—C64—Cl64 | −175.3 (3) |
C23—C24—C25—C26 | 0.0 | C63—C64—C65—C66 | 0.0 |
Cl24—C24—C25—C26 | 178.1 (3) | Cl64—C64—C65—C66 | 175.2 (3) |
C24—C25—C26—C21 | 0.0 | C64—C65—C66—C61 | 0.0 |
C22—C21—C26—C25 | 0.0 | C62—C61—C66—C65 | 0.0 |
N21—C21—C26—C25 | −179.3 (4) | N61—C61—C66—C65 | −178.2 (4) |
C36—N31—C32—C33 | −3.2 (11) | C76—N71—C72—C73 | −2.2 (12) |
C36—N31—C32—Cl3 | 177.7 (5) | C76—N71—C72—Cl7 | 177.1 (5) |
N31—C32—C33—C34 | 4.0 (12) | N71—C72—C73—C74 | 2.2 (12) |
Cl3—C32—C33—C34 | −177.0 (5) | Cl7—C72—C73—C74 | −177.1 (6) |
N31—C32—C33—C37 | −174.9 (7) | N71—C72—C73—C77 | −174.8 (7) |
Cl3—C32—C33—C37 | 4.1 (11) | Cl7—C72—C73—C77 | 5.9 (11) |
C32—C33—C34—C35 | −5.8 (11) | C72—C73—C74—C75 | −5.3 (11) |
C37—C33—C34—C35 | 173.1 (7) | C77—C73—C74—C75 | 171.7 (7) |
C33—C34—C35—C36 | 6.7 (11) | C73—C74—C75—C76 | 8.1 (11) |
C32—N31—C36—C35 | 3.6 (9) | C72—N71—C76—C75 | 4.7 (10) |
C34—C35—C36—N31 | −5.6 (10) | C74—C75—C76—N71 | −7.9 (10) |
C32—C33—C37—O3 | 39.5 (12) | C72—C73—C77—O7 | 39.2 (12) |
C34—C33—C37—O3 | −139.3 (8) | C74—C73—C77—O7 | −137.6 (8) |
C32—C33—C37—N41 | −137.9 (8) | C72—C73—C77—N81 | −138.0 (8) |
C34—C33—C37—N41 | 43.3 (10) | C74—C73—C77—N81 | 45.2 (10) |
O3—C37—N41—C41 | 5.9 (11) | O7—C77—N81—C81 | 5.8 (11) |
C33—C37—N41—C41 | −176.7 (6) | C73—C77—N81—C81 | −176.9 (6) |
C37—N41—C41—C42 | −148.6 (5) | C77—N81—C81—C82 | 144.9 (5) |
C37—N41—C41—C46 | 35.1 (7) | C77—N81—C81—C86 | −34.2 (8) |
C46—C41—C42—C43 | 0.0 | N81—C81—C82—C83 | −179.2 (4) |
N41—C41—C42—C43 | −176.4 (4) | C86—C81—C82—C83 | 0.0 |
C41—C42—C43—C44 | 0.0 | C81—C82—C83—C84 | 0.0 |
C42—C43—C44—C45 | 0.0 | C82—C83—C84—C85 | 0.0 |
C42—C43—C44—Cl44 | 180.0 (3) | C82—C83—C84—Cl84 | 177.3 (3) |
C43—C44—C45—C46 | 0.0 | C83—C84—C85—C86 | 0.0 |
Cl44—C44—C45—C46 | 180.0 (3) | Cl84—C84—C85—C86 | −177.3 (3) |
C44—C45—C46—C41 | 0.0 | C84—C85—C86—C81 | 0.0 |
C42—C41—C46—C45 | 0.0 | N81—C81—C86—C85 | 179.2 (5) |
N41—C41—C46—C45 | 176.2 (5) | C82—C81—C86—C85 | 0.0 |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O1i | 0.88 | 2.11 | 2.925 (8) | 153 |
N41—H41···O3i | 0.88 | 2.00 | 2.833 (8) | 157 |
N61—H61···O5ii | 0.88 | 2.11 | 2.925 (8) | 153 |
N81—H81···O7ii | 0.88 | 2.00 | 2.841 (8) | 159 |
C26—H26···Cg5 | 0.95 | 2.76 | 3.444 (8) | 130 |
C46—H46···Cg4 | 0.95 | 2.75 | 3.448 (8) | 131 |
C62—H62···Cg3ii | 0.95 | 2.88 | 3.588 (8) | 132 |
C82—H82···Cg2ii | 0.95 | 2.87 | 3.579 (8) | 132 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
C12H8BrClN2O | F(000) = 616 |
Mr = 311.56 | Dx = 1.727 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2736 reflections |
a = 4.8810 (2) Å | θ = 3.1–27.5° |
b = 13.3448 (2) Å | µ = 3.64 mm−1 |
c = 18.3974 (3) Å | T = 120 K |
V = 1198.33 (6) Å3 | Block, colourless |
Z = 4 | 0.16 × 0.16 × 0.16 mm |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 2736 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2597 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ & ω scans | h = −6→6 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −17→17 |
Tmin = 0.558, Tmax = 0.558 | l = −23→23 |
36201 measured reflections |
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)] = 0.023 | H-atom parameters constrained |
wR(F2) = 0.060 | w = 1/[σ2(Fo2) + (0.0339P)2 + 0.2964P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
2736 reflections | Δρmax = 0.43 e Å−3 |
154 parameters | Δρmin = −0.52 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1098 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.031 (7) |
C12H8BrClN2O | V = 1198.33 (6) Å3 |
Mr = 311.56 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 4.8810 (2) Å | µ = 3.64 mm−1 |
b = 13.3448 (2) Å | T = 120 K |
c = 18.3974 (3) Å | 0.16 × 0.16 × 0.16 mm |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 2736 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2597 reflections with I > 2σ(I) |
Tmin = 0.558, Tmax = 0.558 | Rint = 0.047 |
36201 measured reflections |
R[F2 > 2σ(F2)] = 0.023 | H-atom parameters constrained |
wR(F2) = 0.060 | Δρmax = 0.43 e Å−3 |
S = 1.07 | Δρmin = −0.52 e Å−3 |
2736 reflections | Absolute structure: Flack (1983), 1098 Friedel pairs |
154 parameters | Absolute structure parameter: 0.031 (7) |
0 restraints |
x | y | z | Uiso*/Ueq | ||
N11 | 0.2251 (4) | 0.44892 (15) | 0.25022 (11) | 0.0305 (4) | |
C12 | 0.3184 (4) | 0.53761 (16) | 0.27104 (11) | 0.0233 (4) | |
Cl1 | 0.20925 (12) | 0.63776 (4) | 0.21708 (3) | 0.03344 (13) | |
C13 | 0.5004 (4) | 0.55387 (15) | 0.32813 (11) | 0.0212 (4) | |
C14 | 0.6017 (5) | 0.46884 (16) | 0.36219 (12) | 0.0282 (5) | |
C15 | 0.5092 (5) | 0.37504 (17) | 0.34193 (13) | 0.0350 (5) | |
C16 | 0.3191 (5) | 0.36907 (17) | 0.28653 (13) | 0.0344 (5) | |
C17 | 0.5980 (4) | 0.65411 (16) | 0.35532 (10) | 0.0218 (4) | |
O1 | 0.8431 (3) | 0.66775 (13) | 0.36577 (10) | 0.0359 (4) | |
N21 | 0.4029 (3) | 0.72119 (12) | 0.37036 (9) | 0.0212 (3) | |
C21 | 0.4464 (4) | 0.81970 (14) | 0.39778 (10) | 0.0201 (4) | |
C22 | 0.2741 (4) | 0.89596 (16) | 0.37318 (12) | 0.0261 (4) | |
C23 | 0.3060 (5) | 0.99245 (16) | 0.39955 (12) | 0.0275 (5) | |
C24 | 0.5085 (4) | 1.01185 (14) | 0.44999 (11) | 0.0242 (4) | |
Br24 | 0.55925 (5) | 1.144725 (15) | 0.484926 (12) | 0.03552 (8) | |
C25 | 0.6793 (4) | 0.93690 (16) | 0.47524 (11) | 0.0256 (4) | |
C26 | 0.6465 (4) | 0.83994 (16) | 0.44923 (11) | 0.0236 (4) | |
H14 | 0.7351 | 0.4751 | 0.3995 | 0.037* | |
H15 | 0.5746 | 0.3163 | 0.3654 | 0.045* | |
H16 | 0.2512 | 0.3048 | 0.2735 | 0.045* | |
H21 | 0.2466 | 0.7057 | 0.3631 | 0.025* | |
H22 | 0.1355 | 0.8817 | 0.3385 | 0.034* | |
H23 | 0.1895 | 1.0448 | 0.3831 | 0.036* | |
H25 | 0.8176 | 0.9516 | 0.5100 | 0.033* | |
H26 | 0.7609 | 0.7876 | 0.4666 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0325 (10) | 0.0286 (10) | 0.0305 (10) | −0.0047 (8) | 0.0013 (8) | −0.0098 (8) |
C12 | 0.0242 (10) | 0.0250 (10) | 0.0206 (10) | 0.0007 (8) | 0.0021 (8) | −0.0028 (8) |
Cl1 | 0.0459 (3) | 0.0307 (3) | 0.0237 (2) | 0.0034 (3) | −0.0106 (2) | −0.0017 (2) |
C13 | 0.0205 (9) | 0.0238 (10) | 0.0192 (9) | 0.0000 (7) | 0.0044 (7) | −0.0029 (8) |
C14 | 0.0332 (11) | 0.0288 (11) | 0.0225 (10) | 0.0030 (9) | 0.0007 (9) | −0.0021 (8) |
C15 | 0.0501 (14) | 0.0249 (11) | 0.0299 (11) | 0.0034 (10) | 0.0038 (10) | 0.0000 (9) |
C16 | 0.0425 (12) | 0.0213 (11) | 0.0393 (13) | −0.0059 (10) | 0.0090 (10) | −0.0085 (10) |
C17 | 0.0199 (9) | 0.0259 (10) | 0.0196 (9) | −0.0037 (9) | 0.0019 (7) | −0.0015 (8) |
O1 | 0.0187 (7) | 0.0393 (10) | 0.0497 (10) | −0.0021 (7) | −0.0010 (7) | −0.0161 (8) |
N21 | 0.0178 (8) | 0.0224 (8) | 0.0232 (8) | −0.0042 (7) | −0.0028 (7) | −0.0034 (7) |
C21 | 0.0204 (9) | 0.0206 (9) | 0.0192 (9) | −0.0027 (8) | 0.0016 (8) | −0.0006 (7) |
C22 | 0.0243 (10) | 0.0297 (11) | 0.0243 (10) | 0.0003 (9) | −0.0049 (8) | 0.0007 (8) |
C23 | 0.0286 (11) | 0.0245 (10) | 0.0293 (12) | 0.0040 (9) | −0.0009 (9) | 0.0017 (9) |
C24 | 0.0340 (12) | 0.0175 (9) | 0.0210 (9) | −0.0035 (8) | 0.0055 (8) | −0.0006 (7) |
Br24 | 0.05752 (15) | 0.01955 (11) | 0.02950 (12) | −0.00444 (10) | 0.00210 (10) | −0.00290 (9) |
C25 | 0.0284 (10) | 0.0255 (10) | 0.0228 (10) | −0.0042 (8) | −0.0060 (8) | −0.0025 (8) |
C26 | 0.0247 (9) | 0.0235 (10) | 0.0225 (9) | −0.0016 (8) | −0.0045 (8) | 0.0004 (8) |
N11—C12 | 1.325 (3) | N21—C21 | 1.424 (2) |
N11—C16 | 1.339 (3) | N21—H21 | 0.8017 |
C12—C13 | 1.393 (3) | C21—C26 | 1.387 (3) |
C12—Cl1 | 1.748 (2) | C21—C22 | 1.395 (3) |
C13—C14 | 1.387 (3) | C22—C23 | 1.385 (3) |
C13—C17 | 1.506 (3) | C22—H22 | 0.95 |
C14—C15 | 1.382 (3) | C23—C24 | 1.381 (3) |
C14—H14 | 0.95 | C23—H23 | 0.95 |
C15—C16 | 1.381 (4) | C24—C25 | 1.382 (3) |
C15—H15 | 0.95 | C24—Br24 | 1.9022 (19) |
C16—H16 | 0.95 | C25—C26 | 1.389 (3) |
C17—O1 | 1.225 (3) | C25—H25 | 0.95 |
C17—N21 | 1.336 (3) | C26—H26 | 0.95 |
C12—N11—C16 | 116.70 (19) | C17—N21—H21 | 118.1 |
N11—C12—C13 | 125.2 (2) | C21—N21—H21 | 116.0 |
N11—C12—Cl1 | 114.47 (16) | C26—C21—C22 | 120.24 (19) |
C13—C12—Cl1 | 120.23 (17) | C26—C21—N21 | 121.77 (18) |
C14—C13—C12 | 116.14 (19) | C22—C21—N21 | 117.95 (18) |
C14—C13—C17 | 117.63 (17) | C23—C22—C21 | 119.8 (2) |
C12—C13—C17 | 126.23 (19) | C23—C22—H22 | 120.1 |
C15—C14—C13 | 120.2 (2) | C21—C22—H22 | 120.1 |
C15—C14—H14 | 119.9 | C24—C23—C22 | 119.3 (2) |
C13—C14—H14 | 119.9 | C24—C23—H23 | 120.3 |
C16—C15—C14 | 118.1 (2) | C22—C23—H23 | 120.3 |
C16—C15—H15 | 120.9 | C23—C24—C25 | 121.47 (19) |
C14—C15—H15 | 120.9 | C23—C24—Br24 | 119.68 (16) |
N11—C16—C15 | 123.5 (2) | C25—C24—Br24 | 118.84 (16) |
N11—C16—H16 | 118.2 | C24—C25—C26 | 119.25 (19) |
C15—C16—H16 | 118.2 | C24—C25—H25 | 120.4 |
O1—C17—N21 | 124.3 (2) | C26—C25—H25 | 120.4 |
O1—C17—C13 | 119.55 (18) | C21—C26—C25 | 119.86 (19) |
N21—C17—C13 | 116.01 (16) | C21—C26—H26 | 120.1 |
C17—N21—C21 | 125.86 (17) | C25—C26—H26 | 120.1 |
C16—N11—C12—C13 | −1.3 (3) | O1—C17—N21—C21 | 2.7 (3) |
C16—N11—C12—Cl1 | 175.22 (17) | C13—C17—N21—C21 | 178.86 (17) |
N11—C12—C13—C14 | 4.1 (3) | C17—N21—C21—C26 | −38.6 (3) |
Cl1—C12—C13—C14 | −172.30 (16) | C17—N21—C21—C22 | 143.6 (2) |
N11—C12—C13—C17 | −176.62 (19) | C26—C21—C22—C23 | 0.9 (3) |
Cl1—C12—C13—C17 | 7.0 (3) | N21—C21—C22—C23 | 178.7 (2) |
C12—C13—C14—C15 | −3.8 (3) | C21—C22—C23—C24 | 0.0 (3) |
C17—C13—C14—C15 | 176.82 (19) | C22—C23—C24—C25 | −0.5 (3) |
C13—C14—C15—C16 | 1.1 (3) | C22—C23—C24—Br24 | 178.60 (17) |
C12—N11—C16—C15 | −1.7 (3) | C23—C24—C25—C26 | 0.0 (3) |
C14—C15—C16—N11 | 1.8 (4) | Br24—C24—C25—C26 | −179.05 (16) |
C14—C13—C17—O1 | 46.9 (3) | C22—C21—C26—C25 | −1.3 (3) |
C12—C13—C17—O1 | −132.4 (2) | N21—C21—C26—C25 | −179.10 (19) |
C14—C13—C17—N21 | −129.4 (2) | C24—C25—C26—C21 | 0.9 (3) |
C12—C13—C17—N21 | 51.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O1i | 0.80 | 2.03 | 2.825 (2) | 169 |
C22—H22···N11ii | 0.95 | 2.56 | 3.405 (3) | 148 |
Symmetry codes: (i) x−1, y, z; (ii) −x, y+1/2, −z+1/2. |
C12H8ClIN2O | F(000) = 1376 |
Mr = 358.55 | Dx = 1.868 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2909 reflections |
a = 10.6597 (2) Å | θ = 3.0–27.5° |
b = 25.9833 (3) Å | µ = 2.71 mm−1 |
c = 9.2044 (6) Å | T = 120 K |
V = 2549.38 (18) Å3 | Plate, colourless |
Z = 8 | 0.33 × 0.18 × 0.07 mm |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 2909 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2314 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ϕ & ω scans | h = −13→13 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −32→33 |
Tmin = 0.469, Tmax = 0.833 | l = −11→11 |
19649 measured reflections |
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)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.056 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.026P)2 + 0.5926P] where P = (Fo2 + 2Fc2)/3 |
2909 reflections | (Δ/σ)max = 0.005 |
154 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.78 e Å−3 |
C12H8ClIN2O | V = 2549.38 (18) Å3 |
Mr = 358.55 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 10.6597 (2) Å | µ = 2.71 mm−1 |
b = 25.9833 (3) Å | T = 120 K |
c = 9.2044 (6) Å | 0.33 × 0.18 × 0.07 mm |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 2909 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2314 reflections with I > 2σ(I) |
Tmin = 0.469, Tmax = 0.833 | Rint = 0.038 |
19649 measured reflections |
R[F2 > 2σ(F2)] = 0.023 | 0 restraints |
wR(F2) = 0.056 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.39 e Å−3 |
2909 reflections | Δρmin = −0.78 e Å−3 |
154 parameters |
x | y | z | Uiso*/Ueq | ||
N11 | 0.60356 (18) | 0.11949 (7) | 0.62709 (19) | 0.0203 (4) | |
C12 | 0.6165 (2) | 0.16921 (8) | 0.6038 (2) | 0.0160 (5) | |
Cl1 | 0.76816 (5) | 0.19337 (2) | 0.62506 (6) | 0.02158 (13) | |
C13 | 0.5212 (2) | 0.20242 (8) | 0.5592 (2) | 0.0143 (4) | |
C14 | 0.4040 (2) | 0.18113 (8) | 0.5380 (2) | 0.0203 (5) | |
C15 | 0.3866 (2) | 0.12909 (8) | 0.5640 (2) | 0.0244 (5) | |
C16 | 0.4878 (2) | 0.10011 (8) | 0.6066 (3) | 0.0245 (5) | |
C17 | 0.54567 (19) | 0.25827 (8) | 0.5278 (2) | 0.0149 (4) | |
O1 | 0.55314 (15) | 0.27425 (5) | 0.40199 (16) | 0.0207 (4) | |
N21 | 0.55734 (17) | 0.28802 (7) | 0.64672 (17) | 0.0170 (4) | |
C21 | 0.5942 (2) | 0.34079 (8) | 0.6469 (2) | 0.0171 (5) | |
C22 | 0.6810 (2) | 0.35646 (8) | 0.7503 (2) | 0.0204 (5) | |
C23 | 0.7200 (2) | 0.40740 (8) | 0.7567 (3) | 0.0220 (5) | |
C24 | 0.6721 (2) | 0.44248 (8) | 0.6580 (2) | 0.0190 (5) | |
I24 | 0.741430 (14) | 0.518368 (5) | 0.656374 (16) | 0.02235 (7) | |
C25 | 0.5848 (2) | 0.42725 (8) | 0.5546 (2) | 0.0195 (5) | |
C26 | 0.5448 (2) | 0.37637 (8) | 0.5492 (2) | 0.0186 (5) | |
H14 | 0.3361 | 0.2019 | 0.5059 | 0.026* | |
H15 | 0.3063 | 0.1138 | 0.5526 | 0.032* | |
H16 | 0.4754 | 0.0643 | 0.6226 | 0.032* | |
H21 | 0.5409 | 0.2738 | 0.7313 | 0.022* | |
H22 | 0.7140 | 0.3321 | 0.8172 | 0.027* | |
H23 | 0.7788 | 0.4181 | 0.8280 | 0.029* | |
H25 | 0.5524 | 0.4516 | 0.4875 | 0.025* | |
H26 | 0.4842 | 0.3660 | 0.4795 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0209 (11) | 0.0147 (10) | 0.0253 (10) | 0.0018 (8) | 0.0015 (8) | 0.0022 (8) |
C12 | 0.0160 (12) | 0.0168 (12) | 0.0150 (11) | −0.0013 (9) | 0.0016 (9) | −0.0029 (9) |
Cl1 | 0.0157 (3) | 0.0203 (3) | 0.0288 (3) | −0.0014 (2) | −0.0015 (2) | 0.0029 (2) |
C13 | 0.0191 (12) | 0.0134 (11) | 0.0105 (10) | 0.0016 (9) | 0.0021 (9) | −0.0010 (8) |
C14 | 0.0192 (12) | 0.0188 (12) | 0.0230 (12) | 0.0011 (9) | −0.0050 (10) | 0.0009 (9) |
C15 | 0.0209 (13) | 0.0189 (13) | 0.0334 (14) | −0.0057 (10) | −0.0023 (11) | −0.0028 (10) |
C16 | 0.0290 (15) | 0.0146 (12) | 0.0300 (13) | −0.0048 (10) | 0.0029 (11) | 0.0007 (10) |
C17 | 0.0100 (11) | 0.0154 (11) | 0.0193 (12) | 0.0005 (8) | −0.0004 (9) | 0.0000 (9) |
O1 | 0.0329 (10) | 0.0161 (8) | 0.0132 (8) | 0.0007 (7) | 0.0016 (7) | 0.0012 (6) |
N21 | 0.0265 (11) | 0.0115 (9) | 0.0131 (9) | −0.0038 (8) | 0.0026 (8) | 0.0005 (7) |
C21 | 0.0208 (12) | 0.0146 (11) | 0.0158 (11) | −0.0007 (9) | 0.0039 (9) | −0.0015 (9) |
C22 | 0.0305 (14) | 0.0171 (11) | 0.0137 (10) | 0.0002 (10) | 0.0010 (10) | 0.0015 (9) |
C23 | 0.0304 (14) | 0.0174 (12) | 0.0182 (11) | −0.0048 (10) | −0.0026 (10) | −0.0036 (9) |
C24 | 0.0241 (13) | 0.0096 (11) | 0.0234 (12) | −0.0018 (9) | 0.0059 (10) | −0.0032 (9) |
I24 | 0.02689 (11) | 0.01153 (10) | 0.02863 (11) | −0.00335 (6) | −0.00034 (7) | −0.00170 (6) |
C25 | 0.0185 (12) | 0.0138 (11) | 0.0263 (12) | 0.0028 (9) | 0.0003 (10) | 0.0024 (9) |
C26 | 0.0162 (12) | 0.0173 (11) | 0.0225 (12) | 0.0003 (9) | −0.0005 (9) | −0.0016 (9) |
N11—C12 | 1.317 (3) | N21—C21 | 1.426 (3) |
N11—C16 | 1.346 (3) | N21—H21 | 0.88 |
C12—C13 | 1.395 (3) | C21—C22 | 1.389 (3) |
C12—Cl1 | 1.745 (2) | C21—C26 | 1.393 (3) |
C13—C14 | 1.380 (3) | C22—C23 | 1.388 (3) |
C13—C17 | 1.502 (3) | C22—H22 | 0.95 |
C14—C15 | 1.386 (3) | C23—C24 | 1.384 (3) |
C14—H14 | 0.95 | C23—H23 | 0.95 |
C15—C16 | 1.373 (3) | C24—C25 | 1.388 (3) |
C15—H15 | 0.95 | C24—I24 | 2.106 (2) |
C16—H16 | 0.95 | C25—C26 | 1.390 (3) |
C17—O1 | 1.232 (2) | C25—H25 | 0.95 |
C17—N21 | 1.346 (3) | C26—H26 | 0.95 |
C12—N11—C16 | 116.14 (19) | C17—N21—H21 | 117.3 |
N11—C12—C13 | 125.3 (2) | C21—N21—H21 | 117.3 |
N11—C12—Cl1 | 115.59 (16) | C22—C21—C26 | 120.0 (2) |
C13—C12—Cl1 | 119.03 (16) | C22—C21—N21 | 117.77 (19) |
C14—C13—C12 | 116.93 (19) | C26—C21—N21 | 122.2 (2) |
C14—C13—C17 | 121.16 (18) | C23—C22—C21 | 120.5 (2) |
C12—C13—C17 | 121.83 (19) | C23—C22—H22 | 119.7 |
C13—C14—C15 | 119.2 (2) | C21—C22—H22 | 119.7 |
C13—C14—H14 | 120.4 | C24—C23—C22 | 119.3 (2) |
C15—C14—H14 | 120.4 | C24—C23—H23 | 120.3 |
C16—C15—C14 | 118.6 (2) | C22—C23—H23 | 120.3 |
C16—C15—H15 | 120.7 | C23—C24—C25 | 120.6 (2) |
C14—C15—H15 | 120.7 | C23—C24—I24 | 119.47 (16) |
N11—C16—C15 | 123.7 (2) | C25—C24—I24 | 119.83 (16) |
N11—C16—H16 | 118.1 | C24—C25—C26 | 120.1 (2) |
C15—C16—H16 | 118.1 | C24—C25—H25 | 119.9 |
O1—C17—N21 | 124.37 (19) | C26—C25—H25 | 119.9 |
O1—C17—C13 | 121.16 (18) | C25—C26—C21 | 119.5 (2) |
N21—C17—C13 | 114.47 (18) | C25—C26—H26 | 120.3 |
C17—N21—C21 | 125.33 (18) | C21—C26—H26 | 120.3 |
C16—N11—C12—C13 | −0.6 (3) | O1—C17—N21—C21 | −7.7 (3) |
C16—N11—C12—Cl1 | −178.02 (16) | C13—C17—N21—C21 | 172.75 (19) |
N11—C12—C13—C14 | 0.0 (3) | C17—N21—C21—C22 | −135.9 (2) |
Cl1—C12—C13—C14 | 177.36 (15) | C17—N21—C21—C26 | 45.1 (3) |
N11—C12—C13—C17 | −176.83 (19) | C26—C21—C22—C23 | −0.5 (3) |
Cl1—C12—C13—C17 | 0.5 (3) | N21—C21—C22—C23 | −179.6 (2) |
C12—C13—C14—C15 | 1.1 (3) | C21—C22—C23—C24 | −0.5 (3) |
C17—C13—C14—C15 | 177.99 (19) | C22—C23—C24—C25 | 0.8 (3) |
C13—C14—C15—C16 | −1.6 (3) | C22—C23—C24—I24 | −175.18 (16) |
C12—N11—C16—C15 | 0.0 (3) | C23—C24—C25—C26 | −0.1 (3) |
C14—C15—C16—N11 | 1.1 (4) | I24—C24—C25—C26 | 175.85 (16) |
C14—C13—C17—O1 | −73.6 (3) | C24—C25—C26—C21 | −0.9 (3) |
C12—C13—C17—O1 | 103.1 (2) | C22—C21—C26—C25 | 1.2 (3) |
C14—C13—C17—N21 | 106.0 (2) | N21—C21—C26—C25 | −179.80 (19) |
C12—C13—C17—N21 | −77.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O1i | 0.88 | 2.01 | 2.853 (2) | 160 |
C15—H15···Cg2ii | 0.95 | 2.65 | 3.404 (2) | 137 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x−2, y+1, z. |
C13H11ClN2O2 | F(000) = 544 |
Mr = 262.69 | Dx = 1.441 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 2661 reflections |
a = 4.8536 (2) Å | θ = 3.6–27.5° |
b = 11.8437 (4) Å | µ = 0.31 mm−1 |
c = 21.0612 (7) Å | T = 120 K |
V = 1210.69 (6) Å3 | Block, colourless |
Z = 4 | 0.34 × 0.22 × 0.12 mm |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 2661 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2184 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.6° |
ϕ & ω scans | h = −5→6 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −15→11 |
Tmin = 0.921, Tmax = 0.964 | l = −21→27 |
7884 measured reflections |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0579P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2661 reflections | Δρmax = 0.24 e Å−3 |
164 parameters | Δρmin = −0.35 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1013 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.05 (7) |
C13H11ClN2O2 | V = 1210.69 (6) Å3 |
Mr = 262.69 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 4.8536 (2) Å | µ = 0.31 mm−1 |
b = 11.8437 (4) Å | T = 120 K |
c = 21.0612 (7) Å | 0.34 × 0.22 × 0.12 mm |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 2661 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2184 reflections with I > 2σ(I) |
Tmin = 0.921, Tmax = 0.964 | Rint = 0.040 |
7884 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.104 | Δρmax = 0.24 e Å−3 |
S = 1.04 | Δρmin = −0.35 e Å−3 |
2661 reflections | Absolute structure: Flack (1983), 1013 Friedel pairs |
164 parameters | Absolute structure parameter: −0.05 (7) |
0 restraints |
x | y | z | Uiso*/Ueq | ||
N11 | 0.2528 (4) | 0.42072 (18) | 0.20676 (9) | 0.0307 (5) | |
C12 | 0.3347 (4) | 0.3434 (2) | 0.24770 (10) | 0.0227 (5) | |
Cl1 | 0.56547 (12) | 0.24507 (5) | 0.21709 (3) | 0.03297 (19) | |
C13 | 0.2436 (4) | 0.33534 (18) | 0.31091 (9) | 0.0177 (5) | |
C14 | 0.0515 (4) | 0.41567 (19) | 0.33018 (10) | 0.0208 (5) | |
C15 | −0.0354 (5) | 0.4982 (2) | 0.28822 (11) | 0.0267 (5) | |
C16 | 0.0687 (5) | 0.4970 (2) | 0.22747 (11) | 0.0331 (6) | |
C17 | 0.3486 (4) | 0.24784 (19) | 0.35626 (9) | 0.0182 (4) | |
O1 | 0.5965 (3) | 0.22805 (14) | 0.36182 (7) | 0.0282 (4) | |
N21 | 0.1514 (4) | 0.19607 (16) | 0.39034 (8) | 0.0183 (4) | |
C21 | 0.1969 (4) | 0.11043 (18) | 0.43713 (9) | 0.0182 (5) | |
C22 | 0.0365 (5) | 0.1129 (2) | 0.49195 (10) | 0.0215 (5) | |
C23 | 0.0673 (5) | 0.0297 (2) | 0.53731 (10) | 0.0245 (5) | |
C24 | 0.2577 (5) | −0.0565 (2) | 0.52849 (9) | 0.0212 (5) | |
O24 | 0.2684 (3) | −0.13507 (14) | 0.57646 (7) | 0.0285 (4) | |
C241 | 0.4823 (5) | −0.2180 (2) | 0.57344 (11) | 0.0314 (6) | |
C25 | 0.4176 (5) | −0.0590 (2) | 0.47362 (10) | 0.0225 (5) | |
C26 | 0.3853 (4) | 0.02478 (19) | 0.42806 (10) | 0.0218 (5) | |
H14 | −0.0200 | 0.4138 | 0.3722 | 0.027* | |
H15 | −0.1638 | 0.5543 | 0.3011 | 0.035* | |
H16 | 0.0070 | 0.5532 | 0.1986 | 0.043* | |
H21 | −0.0202 | 0.2166 | 0.3833 | 0.022* | |
H22 | −0.0939 | 0.1717 | 0.4981 | 0.028* | |
H23 | −0.0421 | 0.0314 | 0.5747 | 0.032* | |
H24A | 0.4653 | −0.2610 | 0.5339 | 0.041* | |
H24B | 0.4660 | −0.2694 | 0.6097 | 0.041* | |
H12C | 0.6622 | −0.1805 | 0.5747 | 0.041* | |
H25 | 0.5482 | −0.1177 | 0.4674 | 0.029* | |
H26 | 0.4934 | 0.0230 | 0.3905 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0356 (11) | 0.0325 (12) | 0.0241 (10) | −0.0033 (11) | 0.0013 (9) | 0.0069 (9) |
C12 | 0.0179 (11) | 0.0260 (14) | 0.0242 (11) | −0.0046 (10) | 0.0031 (10) | −0.0039 (10) |
Cl1 | 0.0300 (3) | 0.0373 (4) | 0.0316 (3) | 0.0010 (3) | 0.0104 (2) | −0.0087 (3) |
C13 | 0.0130 (9) | 0.0202 (13) | 0.0197 (10) | −0.0033 (9) | −0.0041 (9) | −0.0016 (9) |
C14 | 0.0181 (10) | 0.0221 (13) | 0.0223 (10) | −0.0025 (10) | −0.0004 (9) | −0.0023 (9) |
C15 | 0.0256 (12) | 0.0189 (12) | 0.0357 (13) | 0.0024 (11) | −0.0031 (12) | 0.0023 (10) |
C16 | 0.0372 (15) | 0.0283 (15) | 0.0337 (13) | 0.0024 (13) | −0.0053 (12) | 0.0109 (10) |
C17 | 0.0166 (10) | 0.0173 (11) | 0.0206 (9) | −0.0010 (10) | −0.0021 (8) | −0.0040 (9) |
O1 | 0.0124 (7) | 0.0343 (10) | 0.0378 (8) | −0.0011 (8) | −0.0020 (7) | 0.0081 (8) |
N21 | 0.0112 (8) | 0.0225 (11) | 0.0211 (9) | 0.0035 (8) | −0.0011 (7) | 0.0023 (8) |
C21 | 0.0173 (11) | 0.0187 (13) | 0.0185 (11) | −0.0018 (9) | −0.0027 (9) | −0.0009 (9) |
C22 | 0.0188 (11) | 0.0209 (13) | 0.0247 (10) | 0.0025 (10) | 0.0008 (9) | −0.0013 (9) |
C23 | 0.0259 (12) | 0.0280 (14) | 0.0195 (10) | 0.0019 (11) | 0.0046 (10) | −0.0029 (9) |
C24 | 0.0249 (11) | 0.0206 (13) | 0.0182 (10) | −0.0011 (11) | −0.0029 (9) | 0.0010 (9) |
O24 | 0.0347 (9) | 0.0268 (10) | 0.0242 (8) | 0.0050 (9) | 0.0021 (8) | 0.0074 (7) |
C241 | 0.0329 (13) | 0.0312 (15) | 0.0300 (12) | 0.0041 (12) | −0.0035 (11) | 0.0074 (11) |
C25 | 0.0184 (11) | 0.0216 (13) | 0.0274 (11) | 0.0076 (11) | −0.0007 (10) | 0.0006 (9) |
C26 | 0.0196 (11) | 0.0265 (13) | 0.0192 (10) | 0.0031 (10) | 0.0035 (9) | 0.0002 (9) |
N11—C12 | 1.319 (3) | C21—C26 | 1.379 (3) |
N11—C16 | 1.344 (3) | C21—C22 | 1.393 (3) |
C12—C13 | 1.406 (3) | C22—C23 | 1.381 (3) |
C12—Cl1 | 1.740 (2) | C22—H22 | 0.95 |
C13—C14 | 1.393 (3) | C23—C24 | 1.389 (3) |
C13—C17 | 1.499 (3) | C23—H23 | 0.95 |
C14—C15 | 1.384 (3) | C24—O24 | 1.375 (3) |
C14—H14 | 0.95 | C24—C25 | 1.393 (3) |
C15—C16 | 1.376 (3) | O24—C241 | 1.431 (3) |
C15—H15 | 0.95 | C241—H24A | 0.98 |
C16—H16 | 0.95 | C241—H24B | 0.98 |
C17—O1 | 1.231 (2) | C241—H12C | 0.98 |
C17—N21 | 1.344 (3) | C25—C26 | 1.389 (3) |
N21—C21 | 1.431 (3) | C25—H25 | 0.95 |
N21—H21 | 0.88 | C26—H26 | 0.95 |
C12—N11—C16 | 117.07 (19) | C22—C21—N21 | 117.99 (18) |
N11—C12—C13 | 124.9 (2) | C23—C22—C21 | 119.9 (2) |
N11—C12—Cl1 | 114.61 (17) | C23—C22—H22 | 120.1 |
C13—C12—Cl1 | 120.50 (18) | C21—C22—H22 | 120.1 |
C14—C13—C12 | 116.1 (2) | C22—C23—C24 | 120.3 (2) |
C14—C13—C17 | 120.95 (18) | C22—C23—H23 | 119.9 |
C12—C13—C17 | 122.9 (2) | C24—C23—H23 | 119.9 |
C15—C14—C13 | 120.1 (2) | O24—C24—C23 | 115.13 (19) |
C15—C14—H14 | 120.0 | O24—C24—C25 | 125.1 (2) |
C13—C14—H14 | 120.0 | C23—C24—C25 | 119.8 (2) |
C16—C15—C14 | 118.3 (2) | C24—O24—C241 | 117.39 (17) |
C16—C15—H15 | 120.8 | O24—C241—H24A | 109.5 |
C14—C15—H15 | 120.8 | O24—C241—H24B | 109.5 |
N11—C16—C15 | 123.6 (2) | H24A—C241—H24B | 109.5 |
N11—C16—H16 | 118.2 | O24—C241—H12C | 109.5 |
C15—C16—H16 | 118.2 | H24A—C241—H12C | 109.5 |
O1—C17—N21 | 123.9 (2) | H24B—C241—H12C | 109.5 |
O1—C17—C13 | 121.64 (19) | C26—C25—C24 | 119.7 (2) |
N21—C17—C13 | 114.43 (17) | C26—C25—H25 | 120.2 |
C17—N21—C21 | 125.51 (17) | C24—C25—H25 | 120.2 |
C17—N21—H21 | 117.2 | C21—C26—C25 | 120.30 (19) |
C21—N21—H21 | 117.2 | C21—C26—H26 | 119.9 |
C26—C21—C22 | 120.1 (2) | C25—C26—H26 | 119.9 |
C26—C21—N21 | 121.89 (17) | ||
C16—N11—C12—C13 | 0.0 (3) | C13—C17—N21—C21 | −179.40 (17) |
C16—N11—C12—Cl1 | 178.26 (19) | C17—N21—C21—C26 | −41.5 (3) |
N11—C12—C13—C14 | 0.4 (3) | C17—N21—C21—C22 | 141.0 (2) |
Cl1—C12—C13—C14 | −177.73 (16) | C26—C21—C22—C23 | 0.3 (3) |
N11—C12—C13—C17 | −178.3 (2) | N21—C21—C22—C23 | 177.8 (2) |
Cl1—C12—C13—C17 | 3.6 (3) | C21—C22—C23—C24 | 0.0 (3) |
C12—C13—C14—C15 | −1.0 (3) | C22—C23—C24—O24 | −179.4 (2) |
C17—C13—C14—C15 | 177.7 (2) | C22—C23—C24—C25 | −0.1 (3) |
C13—C14—C15—C16 | 1.2 (3) | C23—C24—O24—C241 | −172.87 (19) |
C12—N11—C16—C15 | 0.1 (4) | C25—C24—O24—C241 | 7.9 (3) |
C14—C15—C16—N11 | −0.8 (4) | O24—C24—C25—C26 | 179.2 (2) |
C14—C13—C17—O1 | −131.8 (2) | C23—C24—C25—C26 | −0.1 (3) |
C12—C13—C17—O1 | 46.8 (3) | C22—C21—C26—C25 | −0.5 (3) |
C14—C13—C17—N21 | 46.9 (3) | N21—C21—C26—C25 | −177.90 (19) |
C12—C13—C17—N21 | −134.5 (2) | C24—C25—C26—C21 | 0.4 (3) |
O1—C17—N21—C21 | −0.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O1i | 0.88 | 1.92 | 2.785 (2) | 168 |
Symmetry code: (i) x−1, y, z. |
C13H8ClN3O | Z = 4 |
Mr = 257.67 | F(000) = 528 |
Triclinic, P1 | Dx = 1.461 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2885 (3) Å | Cell parameters from 5365 reflections |
b = 7.7607 (3) Å | θ = 2.9–27.6° |
c = 20.8849 (9) Å | µ = 0.32 mm−1 |
α = 96.456 (2)° | T = 120 K |
β = 92.913 (2)° | Block, colourless |
γ = 91.810 (2)° | 0.40 × 0.10 × 0.10 mm |
V = 1171.49 (8) Å3 |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 5365 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 3760 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.6°, θmin = 2.9° |
ϕ & ω scans | h = −9→9 |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | k = −10→10 |
Tmin = 0.899, Tmax = 0.969 | l = −27→26 |
21639 measured reflections |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0844P)2 + 1.0407P] where P = (Fo2 + 2Fc2)/3 |
5365 reflections | (Δ/σ)max < 0.001 |
325 parameters | Δρmax = 0.74 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C13H8ClN3O | γ = 91.810 (2)° |
Mr = 257.67 | V = 1171.49 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.2885 (3) Å | Mo Kα radiation |
b = 7.7607 (3) Å | µ = 0.32 mm−1 |
c = 20.8849 (9) Å | T = 120 K |
α = 96.456 (2)° | 0.40 × 0.10 × 0.10 mm |
β = 92.913 (2)° |
Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | 5365 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 3760 reflections with I > 2σ(I) |
Tmin = 0.899, Tmax = 0.969 | Rint = 0.060 |
21639 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.74 e Å−3 |
5365 reflections | Δρmin = −0.35 e Å−3 |
325 parameters |
x | y | z | Uiso*/Ueq | ||
N11 | 0.4024 (3) | 0.5334 (3) | 0.41399 (12) | 0.0257 (6) | |
C12 | 0.5406 (4) | 0.4277 (4) | 0.40989 (14) | 0.0225 (6) | |
Cl11 | 0.74241 (10) | 0.51557 (10) | 0.38256 (4) | 0.0285 (2) | |
C13 | 0.5387 (4) | 0.2603 (4) | 0.42747 (14) | 0.0206 (6) | |
C14 | 0.3775 (4) | 0.2012 (4) | 0.45139 (15) | 0.0241 (7) | |
C15 | 0.2276 (4) | 0.3077 (4) | 0.45524 (15) | 0.0268 (7) | |
C16 | 0.2475 (4) | 0.4714 (4) | 0.43607 (15) | 0.0279 (7) | |
C17 | 0.7039 (4) | 0.1471 (4) | 0.42314 (14) | 0.0211 (6) | |
O11 | 0.7924 (3) | 0.1170 (3) | 0.47166 (10) | 0.0273 (5) | |
N21 | 0.7375 (3) | 0.0842 (3) | 0.36189 (12) | 0.0235 (6) | |
C21 | 0.8926 (4) | −0.0042 (4) | 0.33945 (14) | 0.0209 (6) | |
C22 | 0.9149 (4) | −0.0138 (4) | 0.27334 (15) | 0.0232 (6) | |
C23 | 1.0691 (4) | −0.0867 (4) | 0.24724 (15) | 0.0244 (7) | |
C24 | 1.2018 (4) | −0.1517 (4) | 0.28771 (15) | 0.0221 (6) | |
C241 | 1.3665 (4) | −0.2196 (4) | 0.26069 (15) | 0.0263 (7) | |
N24 | 1.4970 (4) | −0.2700 (4) | 0.23738 (14) | 0.0340 (7) | |
C25 | 1.1762 (4) | −0.1476 (4) | 0.35319 (15) | 0.0224 (6) | |
C26 | 1.0208 (4) | −0.0761 (4) | 0.37956 (15) | 0.0221 (6) | |
N31 | −0.5598 (3) | 1.0705 (3) | 0.08089 (12) | 0.0251 (6) | |
C32 | −0.4236 (4) | 0.9650 (4) | 0.08737 (14) | 0.0203 (6) | |
Cl31 | −0.21001 (10) | 1.06368 (10) | 0.11310 (4) | 0.0268 (2) | |
C33 | −0.4379 (4) | 0.7849 (4) | 0.07404 (14) | 0.0194 (6) | |
C34 | −0.6107 (4) | 0.7128 (4) | 0.05231 (15) | 0.0244 (7) | |
C35 | −0.7567 (4) | 0.8212 (4) | 0.04530 (15) | 0.0266 (7) | |
C36 | −0.7249 (4) | 0.9975 (4) | 0.05984 (15) | 0.0279 (7) | |
C37 | −0.2739 (4) | 0.6719 (4) | 0.07828 (14) | 0.0193 (6) | |
O31 | −0.1832 (3) | 0.6369 (3) | 0.03110 (10) | 0.0257 (5) | |
N41 | −0.2429 (3) | 0.6166 (3) | 0.13691 (12) | 0.0221 (5) | |
C41 | −0.0939 (4) | 0.5220 (4) | 0.15886 (14) | 0.0192 (6) | |
C42 | −0.0933 (4) | 0.4872 (4) | 0.22279 (15) | 0.0238 (7) | |
C43 | 0.0521 (4) | 0.4041 (4) | 0.24920 (15) | 0.0246 (7) | |
C44 | 0.1995 (4) | 0.3559 (4) | 0.21195 (15) | 0.0220 (6) | |
C441 | 0.3543 (4) | 0.2754 (4) | 0.23969 (15) | 0.0259 (7) | |
N44 | 0.4780 (4) | 0.2120 (4) | 0.26268 (14) | 0.0326 (6) | |
C45 | 0.1955 (4) | 0.3863 (4) | 0.14756 (14) | 0.0216 (6) | |
C46 | 0.0501 (4) | 0.4687 (4) | 0.12041 (14) | 0.0217 (6) | |
H14 | 0.3693 | 0.0887 | 0.4651 | 0.029* | |
H15 | 0.1148 | 0.2689 | 0.4706 | 0.032* | |
H16 | 0.1453 | 0.5443 | 0.4387 | 0.034* | |
H21 | 0.6517 | 0.1005 | 0.3322 | 0.028* | |
H22 | 0.8237 | 0.0299 | 0.2460 | 0.028* | |
H23 | 1.0845 | −0.0924 | 0.2022 | 0.029* | |
H25 | 1.2659 | −0.1942 | 0.3803 | 0.027* | |
H26 | 1.0021 | −0.0761 | 0.4242 | 0.027* | |
H34 | −0.6284 | 0.5908 | 0.0424 | 0.029* | |
H35 | −0.8757 | 0.7748 | 0.0308 | 0.032* | |
H36 | −0.8248 | 1.0714 | 0.0547 | 0.033* | |
H41 | −0.3263 | 0.6429 | 0.1651 | 0.026* | |
H42 | −0.1931 | 0.5208 | 0.2483 | 0.029* | |
H43 | 0.0516 | 0.3798 | 0.2928 | 0.030* | |
H45 | 0.2940 | 0.3500 | 0.1218 | 0.026* | |
H46 | 0.0481 | 0.4887 | 0.0763 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0217 (13) | 0.0263 (14) | 0.0300 (15) | 0.0095 (11) | 0.0027 (11) | 0.0032 (11) |
C12 | 0.0200 (14) | 0.0251 (16) | 0.0229 (15) | 0.0055 (12) | 0.0028 (11) | 0.0029 (12) |
Cl11 | 0.0228 (4) | 0.0318 (4) | 0.0330 (4) | 0.0026 (3) | 0.0089 (3) | 0.0083 (3) |
C13 | 0.0190 (14) | 0.0238 (16) | 0.0195 (14) | 0.0059 (12) | 0.0024 (11) | 0.0023 (11) |
C14 | 0.0186 (15) | 0.0261 (17) | 0.0285 (17) | 0.0043 (12) | 0.0035 (12) | 0.0050 (12) |
C15 | 0.0141 (14) | 0.0328 (18) | 0.0330 (18) | 0.0029 (13) | 0.0042 (12) | −0.0004 (13) |
C16 | 0.0158 (14) | 0.0325 (19) | 0.0346 (18) | 0.0099 (13) | 0.0020 (12) | −0.0030 (14) |
C17 | 0.0184 (14) | 0.0222 (16) | 0.0236 (15) | 0.0023 (12) | 0.0025 (12) | 0.0052 (12) |
O11 | 0.0214 (11) | 0.0361 (13) | 0.0254 (12) | 0.0096 (9) | 0.0015 (9) | 0.0056 (9) |
N21 | 0.0163 (12) | 0.0305 (15) | 0.0241 (13) | 0.0098 (11) | 0.0003 (10) | 0.0029 (11) |
C21 | 0.0162 (14) | 0.0172 (15) | 0.0292 (16) | 0.0039 (11) | 0.0021 (11) | 0.0016 (12) |
C22 | 0.0211 (15) | 0.0232 (16) | 0.0255 (16) | 0.0065 (12) | −0.0008 (12) | 0.0026 (12) |
C23 | 0.0232 (15) | 0.0248 (17) | 0.0255 (16) | 0.0029 (13) | 0.0038 (12) | 0.0019 (12) |
C24 | 0.0151 (14) | 0.0181 (15) | 0.0329 (17) | 0.0031 (11) | 0.0031 (12) | 0.0008 (12) |
C241 | 0.0218 (16) | 0.0243 (17) | 0.0323 (17) | 0.0034 (13) | 0.0009 (13) | 0.0006 (13) |
N24 | 0.0247 (15) | 0.0377 (17) | 0.0402 (17) | 0.0097 (13) | 0.0083 (12) | 0.0017 (13) |
C25 | 0.0172 (14) | 0.0184 (15) | 0.0319 (17) | 0.0071 (11) | −0.0006 (12) | 0.0035 (12) |
C26 | 0.0220 (15) | 0.0202 (15) | 0.0251 (16) | 0.0057 (12) | 0.0038 (12) | 0.0041 (12) |
N31 | 0.0202 (13) | 0.0281 (14) | 0.0280 (14) | 0.0104 (11) | 0.0032 (10) | 0.0043 (11) |
C32 | 0.0133 (13) | 0.0264 (16) | 0.0214 (15) | 0.0034 (12) | 0.0010 (11) | 0.0024 (11) |
Cl31 | 0.0208 (4) | 0.0279 (4) | 0.0309 (4) | 0.0004 (3) | −0.0033 (3) | 0.0022 (3) |
C33 | 0.0174 (14) | 0.0218 (15) | 0.0200 (14) | 0.0028 (11) | 0.0035 (11) | 0.0048 (11) |
C34 | 0.0186 (15) | 0.0247 (16) | 0.0308 (17) | 0.0024 (12) | 0.0020 (12) | 0.0064 (13) |
C35 | 0.0146 (14) | 0.0347 (19) | 0.0317 (17) | −0.0001 (13) | 0.0009 (12) | 0.0097 (14) |
C36 | 0.0211 (15) | 0.0350 (19) | 0.0300 (17) | 0.0137 (14) | 0.0043 (13) | 0.0096 (14) |
C37 | 0.0163 (14) | 0.0174 (15) | 0.0241 (15) | 0.0001 (11) | 0.0017 (11) | 0.0010 (11) |
O31 | 0.0221 (11) | 0.0313 (13) | 0.0247 (11) | 0.0085 (9) | 0.0052 (9) | 0.0040 (9) |
N41 | 0.0165 (12) | 0.0280 (14) | 0.0233 (13) | 0.0093 (10) | 0.0048 (10) | 0.0060 (10) |
C41 | 0.0129 (13) | 0.0176 (15) | 0.0275 (16) | 0.0041 (11) | 0.0013 (11) | 0.0029 (11) |
C42 | 0.0223 (15) | 0.0242 (16) | 0.0262 (16) | 0.0086 (13) | 0.0071 (12) | 0.0043 (12) |
C43 | 0.0233 (15) | 0.0279 (17) | 0.0237 (16) | 0.0070 (13) | 0.0020 (12) | 0.0059 (12) |
C44 | 0.0191 (14) | 0.0155 (15) | 0.0311 (17) | 0.0032 (11) | −0.0015 (12) | 0.0020 (12) |
C441 | 0.0257 (16) | 0.0233 (16) | 0.0290 (17) | 0.0034 (13) | 0.0008 (13) | 0.0043 (13) |
N44 | 0.0280 (15) | 0.0330 (16) | 0.0376 (16) | 0.0111 (12) | −0.0030 (12) | 0.0074 (12) |
C45 | 0.0166 (14) | 0.0187 (15) | 0.0296 (16) | 0.0046 (11) | 0.0030 (12) | 0.0015 (12) |
C46 | 0.0203 (15) | 0.0216 (15) | 0.0242 (15) | 0.0062 (12) | 0.0034 (12) | 0.0049 (12) |
N11—C12 | 1.319 (4) | N31—C32 | 1.318 (4) |
N11—C16 | 1.336 (4) | N31—C36 | 1.345 (4) |
C12—C13 | 1.389 (4) | C32—C33 | 1.394 (4) |
C12—Cl11 | 1.751 (3) | C32—Cl31 | 1.745 (3) |
C13—C14 | 1.385 (4) | C33—C34 | 1.395 (4) |
C13—C17 | 1.513 (4) | C33—C37 | 1.510 (4) |
C14—C15 | 1.391 (4) | C34—C35 | 1.389 (4) |
C14—H14 | 0.95 | C34—H34 | 0.95 |
C15—C16 | 1.380 (5) | C35—C36 | 1.377 (5) |
C15—H15 | 0.95 | C35—H35 | 0.95 |
C16—H16 | 0.95 | C36—H36 | 0.95 |
C17—O11 | 1.222 (3) | C37—O31 | 1.224 (3) |
C17—N21 | 1.354 (4) | C37—N41 | 1.353 (4) |
N21—C21 | 1.414 (4) | N41—C41 | 1.415 (4) |
N21—H21 | 0.88 | N41—H41 | 0.88 |
C21—C22 | 1.392 (4) | C41—C42 | 1.391 (4) |
C21—C26 | 1.395 (4) | C41—C46 | 1.399 (4) |
C22—C23 | 1.383 (4) | C42—C43 | 1.381 (4) |
C22—H22 | 0.95 | C42—H42 | 0.95 |
C23—C24 | 1.396 (4) | C43—C44 | 1.395 (4) |
C23—H23 | 0.95 | C43—H43 | 0.95 |
C24—C25 | 1.387 (4) | C44—C45 | 1.390 (4) |
C24—C241 | 1.442 (4) | C44—C441 | 1.434 (4) |
C241—N24 | 1.150 (4) | C441—N44 | 1.150 (4) |
C25—C26 | 1.389 (4) | C45—C46 | 1.385 (4) |
C25—H25 | 0.95 | C45—H45 | 0.95 |
C26—H26 | 0.95 | C46—H46 | 0.95 |
C12—N11—C16 | 116.5 (3) | C32—N31—C36 | 117.0 (3) |
N11—C12—C13 | 125.5 (3) | N31—C32—C33 | 125.0 (3) |
N11—C12—Cl11 | 115.0 (2) | N31—C32—Cl31 | 116.0 (2) |
C13—C12—Cl11 | 119.4 (2) | C33—C32—Cl31 | 118.9 (2) |
C14—C13—C12 | 116.6 (3) | C32—C33—C34 | 116.7 (3) |
C14—C13—C17 | 120.5 (3) | C32—C33—C37 | 122.5 (3) |
C12—C13—C17 | 122.9 (3) | C34—C33—C37 | 120.7 (3) |
C13—C14—C15 | 119.6 (3) | C35—C34—C33 | 119.4 (3) |
C13—C14—H14 | 120.2 | C35—C34—H34 | 120.3 |
C15—C14—H14 | 120.2 | C33—C34—H34 | 120.3 |
C16—C15—C14 | 118.0 (3) | C36—C35—C34 | 118.5 (3) |
C16—C15—H15 | 121.0 | C36—C35—H35 | 120.8 |
C14—C15—H15 | 121.0 | C34—C35—H35 | 120.8 |
N11—C16—C15 | 123.8 (3) | N31—C36—C35 | 123.4 (3) |
N11—C16—H16 | 118.1 | N31—C36—H36 | 118.3 |
C15—C16—H16 | 118.1 | C35—C36—H36 | 118.3 |
O11—C17—N21 | 125.5 (3) | O31—C37—N41 | 125.9 (3) |
O11—C17—C13 | 121.1 (3) | O31—C37—C33 | 120.3 (3) |
N21—C17—C13 | 113.4 (2) | N41—C37—C33 | 113.9 (2) |
C17—N21—C21 | 128.4 (2) | C37—N41—C41 | 128.5 (2) |
C17—N21—H21 | 115.8 | C37—N41—H41 | 115.8 |
C21—N21—H21 | 115.8 | C41—N41—H41 | 115.8 |
C22—C21—C26 | 120.3 (3) | C42—C41—C46 | 120.2 (3) |
C22—C21—N21 | 116.0 (3) | C42—C41—N41 | 116.4 (2) |
C26—C21—N21 | 123.8 (3) | C46—C41—N41 | 123.3 (3) |
C23—C22—C21 | 120.4 (3) | C43—C42—C41 | 120.2 (3) |
C23—C22—H22 | 119.8 | C43—C42—H42 | 119.9 |
C21—C22—H22 | 119.8 | C41—C42—H42 | 119.9 |
C22—C23—C24 | 119.4 (3) | C42—C43—C44 | 120.0 (3) |
C22—C23—H23 | 120.3 | C42—C43—H43 | 120.0 |
C24—C23—H23 | 120.3 | C44—C43—H43 | 120.0 |
C25—C24—C23 | 120.1 (3) | C45—C44—C43 | 119.5 (3) |
C25—C24—C241 | 120.7 (3) | C45—C44—C441 | 120.1 (3) |
C23—C24—C241 | 119.1 (3) | C43—C44—C441 | 120.4 (3) |
N24—C241—C24 | 177.5 (3) | N44—C441—C44 | 179.1 (4) |
C24—C25—C26 | 120.7 (3) | C46—C45—C44 | 121.0 (3) |
C24—C25—H25 | 119.6 | C46—C45—H45 | 119.5 |
C26—C25—H25 | 119.6 | C44—C45—H45 | 119.5 |
C25—C26—C21 | 119.0 (3) | C45—C46—C41 | 119.0 (3) |
C25—C26—H26 | 120.5 | C45—C46—H46 | 120.5 |
C21—C26—H26 | 120.5 | C41—C46—H46 | 120.5 |
C16—N11—C12—C13 | −1.1 (5) | C36—N31—C32—C33 | 0.1 (4) |
C16—N11—C12—Cl11 | −178.6 (2) | C36—N31—C32—Cl31 | 178.7 (2) |
N11—C12—C13—C14 | −0.2 (5) | N31—C32—C33—C34 | −0.1 (4) |
Cl11—C12—C13—C14 | 177.2 (2) | Cl31—C32—C33—C34 | −178.6 (2) |
N11—C12—C13—C17 | −178.4 (3) | N31—C32—C33—C37 | 175.9 (3) |
Cl11—C12—C13—C17 | −1.0 (4) | Cl31—C32—C33—C37 | −2.7 (4) |
C12—C13—C14—C15 | 1.4 (4) | C32—C33—C34—C35 | −0.1 (4) |
C17—C13—C14—C15 | 179.7 (3) | C37—C33—C34—C35 | −176.2 (3) |
C13—C14—C15—C16 | −1.4 (5) | C33—C34—C35—C36 | 0.4 (4) |
C12—N11—C16—C15 | 1.1 (5) | C32—N31—C36—C35 | 0.2 (4) |
C14—C15—C16—N11 | 0.1 (5) | C34—C35—C36—N31 | −0.4 (5) |
C14—C13—C17—O11 | −70.9 (4) | C32—C33—C37—O31 | −89.6 (4) |
C12—C13—C17—O11 | 107.3 (3) | C34—C33—C37—O31 | 86.2 (4) |
C14—C13—C17—N21 | 108.1 (3) | C32—C33—C37—N41 | 90.9 (3) |
C12—C13—C17—N21 | −73.7 (4) | C34—C33—C37—N41 | −93.3 (3) |
O11—C17—N21—C21 | −10.7 (5) | O31—C37—N41—C41 | 6.3 (5) |
C13—C17—N21—C21 | 170.3 (3) | C33—C37—N41—C41 | −174.2 (3) |
C17—N21—C21—C22 | −163.6 (3) | C37—N41—C41—C42 | 177.8 (3) |
C17—N21—C21—C26 | 15.1 (5) | C37—N41—C41—C46 | −0.3 (5) |
C26—C21—C22—C23 | −3.4 (4) | C46—C41—C42—C43 | 1.8 (5) |
N21—C21—C22—C23 | 175.4 (3) | N41—C41—C42—C43 | −176.4 (3) |
C21—C22—C23—C24 | 0.4 (4) | C41—C42—C43—C44 | 0.5 (5) |
C22—C23—C24—C25 | 1.9 (4) | C42—C43—C44—C45 | −2.4 (5) |
C22—C23—C24—C241 | −177.0 (3) | C42—C43—C44—C441 | 177.6 (3) |
C23—C24—C25—C26 | −1.3 (4) | C43—C44—C45—C46 | 2.1 (4) |
C241—C24—C25—C26 | 177.5 (3) | C441—C44—C45—C46 | −178.0 (3) |
C24—C25—C26—C21 | −1.6 (4) | C44—C45—C46—C41 | 0.2 (4) |
C22—C21—C26—C25 | 3.9 (4) | C42—C41—C46—C45 | −2.1 (4) |
N21—C21—C26—C25 | −174.7 (3) | N41—C41—C46—C45 | 175.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···N44 | 0.88 | 2.15 | 3.006 (4) | 164 |
N41—H41···N24i | 0.88 | 2.10 | 2.978 (4) | 173 |
C14—H14···O11ii | 0.95 | 2.49 | 3.334 (4) | 148 |
C15—H15···O11iii | 0.95 | 2.60 | 3.507 (4) | 160 |
C25—H25···N11iv | 0.95 | 2.52 | 3.348 (4) | 146 |
C34—H34···O31v | 0.95 | 2.53 | 3.327 (4) | 142 |
C35—H35···O31iii | 0.95 | 2.45 | 3.366 (4) | 161 |
C45—H45···N31iv | 0.95 | 2.53 | 3.300 (4) | 138 |
Symmetry codes: (i) x−2, y+1, z; (ii) −x+1, −y, −z+1; (iii) x−1, y, z; (iv) x+1, y−1, z; (v) −x−1, −y+1, −z. |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C12H9ClN2O | C13H11ClN2O | C12H8ClFN2O·H2O | C12H8Cl2N2O |
Mr | 232.66 | 246.69 | 268.67 | 267.10 |
Crystal system, space group | Orthorhombic, Pccn | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21 |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 13.2296 (6), 21.0744 (10), 7.6898 (16) | 9.6824 (6), 11.3082 (7), 11.5139 (7) | 6.8033 (4), 8.1303 (3), 11.5356 (6) | 5.0855 (8), 28.982 (8), 15.607 (4) |
α, β, γ (°) | 90, 90, 90 | 77.453 (2), 73.445 (2), 87.978 (2) | 84.032 (3), 84.297 (2), 69.569 (3) | 90, 90.37 (2), 90 |
V (Å3) | 2144.0 (5) | 1179.07 (13) | 593.32 (5) | 2300.2 (9) |
Z | 8 | 4 | 2 | 8 |
Radiation type | Mo Kα | Synchrotron, λ = 0.67510 Å | Mo Kα | Mo Kα |
µ (mm−1) | 0.33 | 0.31 | 0.33 | 0.55 |
Crystal size (mm) | 0.24 × 0.09 × 0.02 | 0.10 × 0.02 × 0.02 | 0.18 × 0.16 × 0.03 | 0.28 × 0.07 × 0.03 |
Data collection | ||||
Diffractometer | Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | Bruker SMART APEX2 CCD diffractometer | Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer |
Absorption correction | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan Bruker SADABS (Bruker, 2004) | Multi-scan SADABS 2.10 (Sheldrick,. 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) |
Tmin, Tmax | 0.943, 0.993 | 0.970, 0.994 | 0.933, 0.990 | 0.862, 0.984 |
No. of measured, independent and observed reflections | 17837, 2446, 1724 [I > 2σ(I)] | 12982, 6881, 5217 [( > 2σ(I)] | 12303, 2720, 1943 [I > 2σ(I)] | 24726, 9787, 6370 [I > 2σ(I)] |
Rint | 0.104 | 0.022 | 0.052 | 0.053 |
(sin θ/λ)max (Å−1) | 0.650 | 0.714 | 0.655 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.129, 1.07 | 0.044, 0.124, 1.02 | 0.044, 0.113, 1.05 | 0.069, 0.169, 1.04 |
No. of reflections | 2446 | 6881 | 2720 | 9787 |
No. of parameters | 145 | 309 | 163 | 254 |
No. of restraints | 0 | 0 | 0 | 1 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.28 | 0.43, −0.30 | 0.26, −0.29 | 0.79, −0.54 |
Absolute structure | ? | ? | ? | Flack (1983), 4396 Friedel pairs |
Absolute structure parameter | ? | ? | ? | 0.54 (11) |
(V) | (VI) | (VII) | (VIII) | |
Crystal data | ||||
Chemical formula | C12H8BrClN2O | C12H8ClIN2O | C13H11ClN2O2 | C13H8ClN3O |
Mr | 311.56 | 358.55 | 262.69 | 257.67 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, Pbca | Orthorhombic, P212121 | Triclinic, P1 |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 4.8810 (2), 13.3448 (2), 18.3974 (3) | 10.6597 (2), 25.9833 (3), 9.2044 (6) | 4.8536 (2), 11.8437 (4), 21.0612 (7) | 7.2885 (3), 7.7607 (3), 20.8849 (9) |
α, β, γ (°) | 90, 90, 90 | 90, 90, 90 | 90, 90, 90 | 96.456 (2), 92.913 (2), 91.810 (2) |
V (Å3) | 1198.33 (6) | 2549.38 (18) | 1210.69 (6) | 1171.49 (8) |
Z | 4 | 8 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 3.64 | 2.71 | 0.31 | 0.32 |
Crystal size (mm) | 0.16 × 0.16 × 0.16 | 0.33 × 0.18 × 0.07 | 0.34 × 0.22 × 0.12 | 0.40 × 0.10 × 0.10 |
Data collection | ||||
Diffractometer | Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer | Bruker-Nonius 95mm CCD camera on κ goniostat diffractometer |
Absorption correction | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) |
Tmin, Tmax | 0.558, 0.558 | 0.469, 0.833 | 0.921, 0.964 | 0.899, 0.969 |
No. of measured, independent and observed reflections | 36201, 2736, 2597 [I > 2σ(I)] | 19649, 2909, 2314 [I > 2σ(I)] | 7884, 2661, 2184 [I > 2σ(I)] | 21639, 5365, 3760 [I > 2σ(I)] |
Rint | 0.047 | 0.038 | 0.040 | 0.060 |
(sin θ/λ)max (Å−1) | 0.650 | 0.649 | 0.649 | 0.653 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.023, 0.060, 1.07 | 0.023, 0.056, 1.04 | 0.042, 0.104, 1.04 | 0.059, 0.171, 1.07 |
No. of reflections | 2736 | 2909 | 2661 | 5365 |
No. of parameters | 154 | 154 | 164 | 325 |
No. of restraints | 0 | 0 | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.52 | 0.39, −0.78 | 0.24, −0.35 | 0.74, −0.35 |
Absolute structure | Flack (1983), 1098 Friedel pairs | ? | Flack (1983), 1013 Friedel pairs | ? |
Absolute structure parameter | 0.031 (7) | ? | −0.05 (7) | ? |
Computer programs: COLLECT (Hooft, 1999), Bruker APEX2 (Bruker, 2004), DENZO (Otwinowski & Minor, 1997) & COLLECT, SAINT (Bruker, 2004), DENZO & COLLECT, SAINT, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).
Acknowledgements
We thank the EPSRC National Crystallography Service, University of Southampton, UK, for collecting the X-ray data for (I) and (III)–(VIII). Data for (II) were collected on Daresbury SRS Station 9.8, for which we thank the EPSRC-funded synchrotron crystallography service and Professor W. Clegg. JLW and SMSVW thank CNPq and FAPERJ for financial support.
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