Supporting information
CCDC references: 1039216; 1039215; 1039214; 1039213; 1039212; 1039211; 1039210
4-Aminoantipyrine (4-AAP), (I), is an anti-inflammatory agent which is mainly used as a reagent to detect phenols and peroxides (Adam, 2013). The use of 4-AAP as a nonsteroidal anti-inflammatory drug is rare because the drug causes agranulocytosis, i.e. a drop in the number of infection-fighting white blood cells (Adam, 2013). Some derivatives of 4-aminoantipyrines, such as dipyrone – an anti-inflammatory which is still in use – have medicinal properties (Li et al., 2013, and references therein). 4-AAP can be modified easily by reacting it with either an aldehyde, ketone or ester functional group to form Schiff bases and the prepared derivatives then show increased biological activities, such as antitumor, fungicidal, bactericidal, antiviral, anti-inflammatory, antipyretic, analgesic, antiproliferative and antioxidant activities (Cunha et al., 2005; Schilf et al., 2013). Metal complexes of 4-AAP-derived Schiff bases have been prepared and tested for biological activity also (Leelavathy & Antony, 2013; El-Bindary et al., 2013). Molecular salt complexes have also been prepared with quinol and picric acid (Adam, 2013). We synthesized six derivatives of 4-AAP, (II)–(VII) (see Scheme 1), and discuss the changes in molecular packing and hydrogen bonding compared to the parent 4-AAP, (I) (Scheme 1), and to related compounds in the Cambridge Structural Database (CSD, Version 5.34, with a May 2013 update; Groom & Allen, 2014). The derivatization is carried out with the molecules shown in Scheme 2. This report is a continuation of structural studies that look at how the hydrogen bonding changes in a series of related structures by varying the substituents on an organic backbone (Omondi et al., 2009; Lemmerer & Michael, 2010a,b, 2011).
All chemicals were purchased from commercial sources and used as received. Crystals where grown by slow evaporation under ambient conditions of a methanol solution containing a 1:1 ratio of 4-aminoantipyrine and the aldehyde/ketone and ester reactant. The solutions were stirred and heated gently overnight to allow for complete reaction. Detailed masses and volumes are as follows: for (II), 4-AAP (0.100 g, 0.492 mmol) and methyl 3-oxobutanoate (see A in Scheme 2; 0.058 g, 0.500 mmol) in 8 ml methanol; for (III), 4-AAP (0.100 g, 0.492 mmol) and ethyl 3-oxobutanoate (B; 0.065 g, 0.500 mmol) in 8 ml methanol; for (IV), 4-AAP (0.100 g, 0.492 mmol) and ethyl 2-oxocyclohexanecarboxylate (C; 0.085 g, 0.500 mmol) in 8 ml methanol; for (V), 4-AAP (0.100 g, 0.492 mmol) and ethyl 3-oxo-3-phenylpropanoate (D; 0.096 g, 0.500 mmol) in 8 ml methanol; for (VI), 4-AAP (0.100 g, 0.492 mmol) and 4-formylbenzoate (E; 0.082 g, 0.500 mmol) in 8 ml methanol; for (VI), 4-AAP (0.100 g, 0.492 mmol) and ethyl cyanoacetate (F; 0.057 g, 0.500 mmol) in 8 ml methanol.
Cell determination, data collection and structure refinement details are summarized in Table 1. For all compounds, C-bound H atoms were placed geometrically [C—H = C—H = 0.95 (alkene), 0.98 (methylene and CH3), 0.99 (ethylene, –CH2–) or 0.95 Å (aromatic)] and refined as riding, with Uiso(H) = 1.2Ueq(C). N-bound H atoms were located in difference maps and their coordinates allowed to refine freely, with Uiso(H) = 1.5Ueq(N).
In (I), the absolute structure was chosen arbitrarily, and refinement of the absolute structure parameter (Flack & Bernardinelli, 2000) was not posible as molybdenum radiation was used. The Friedel pairs of reflections were thus merged prior to the final refinements. In addition, the crystals of (I) showed twinning, and the twin law (1 0 0 1 1 0 0 0 ¯), with the batch scale factor refining to 0.42502, resulted in a significant improvement of the refinement statistics.
The molecular structures and atomic numbering schemes of the asymmetric units of compounds (I)–(VII) are shown in Fig. 1, and the packing diagrams are shown in Figs. 2–4.
Recently, the room-temperature crystal structure of 4-AAP, (I), was reported (Li et al., 2013; CCDC deposition number 801822). The crystallographic indicators show a poor-quality data set [Rint = 0.097 and R1 (all data) = 0.0992] with low redundancy. Crystals grown from propan-2-ol by us showed bipyramidal crystal habits, and were observed as twinned under polarized light microscopy. We collected a low-temperature data set with the same unit cell as reported previously, with higher redundancy, and after applying a twin law, a much improved set of crystallographic discrepancy factors was obtained. Comparable bond lengths and angles are observed. The asymmetric unit consists of one 4-AAP molecule on a general position in the hexagonal space group P61. The hydrogen bonding involves only one of the H atoms on the amine N3 atom (H3A). This forms a hydrogen bond to carbonyl atom O1i of an adjacent molecule to form an infinite chain with graph set C(4) (Bernstein et al., 1995) (Fig. 2; see Table 2 for hydrogen-bond geometry and symmetry code). Ultimately, by virtue of the sixfold screw axis that defines the chain, a symmetrically pleasing helical form results down the crystallographic c axis (Fig. 3). Adjacent 4-AAP moleclues interact along the b axis by C8—H8···O1 hydrogen bonding [not in Table 2?], and along the a axis, there is a π–π interaction between the benzene (atoms C6–C11) and pyrazole (atoms C1–N1) rings, with a centroid–centroid (Cg···Cgviii) distance of 3.9705 (15) Å [symmetry code: (viii) y, -x+y+1, z+1/6].
The reaction of the ketone group of methyl 3-oxobutanoate with the amine group of 4-AAP produced enamine (II). The formation of an enamine favours the formation of an intramolecular six-membered hydrogen-bonded ring with graph set S(6) (Etter, 1990) involving amine atom H3 to ester carbonyl atom O2 (Fig. 1; see Table 3 for hydrogen-bond geometry). The molecules pack in a head-to-tail fashion along the a axis, with two intermolecular interactions involving π systems (Fig. 4a). Firstly, atom C10 interacts with the centroid (Cg1) of the benzene ring through atom H10 [C10—H10···Cg1ix = 2.75 Å and C10—H10···Cg1viii = 172°; symmetry code: (ix) -x+1, y+1/2, -z+3/2]. Secondly, the five-membered pyrazole ring forms a close contact with the O1 ketone group of a neighbouring inversion-related molecule, such that the centroid of the pyrazole ring (Cg2) has an O1···Cg2iv distance of 3.7581 (12) Å [symmetry code: (iv) -x+1, -y+1, -z+1].
The reaction of the ketone group of ethyl 3-oxobutanoate with the amine group of 4-AAP produced enamine (III). Amine atom H3 forms an intermolecular hydrogen bond with graph set S(6) to ester carbonyl atom O2, similar to (II) (Fig. 1). However, it has additional C—H···O hydrogen-bond interactions, viz. C11—H11···O1ii, forming an R22(12) hydrogen-bonded ring, and C8—H8···O3iii, forming an R44(28) ring (Fig. 4b; see Table 4 for hydrogen-bond geometry and symmetry codes). Additionally, the molecules pack antiparallel along the c axis, stabilized by centrosymmtric π–π interactions between adjacent pyrazole rings [Cg···Cgiv = 3.9668 (9) Å].
The reaction of the ketone group of ethyl 2-oxocyclohexanecarboxylate with the amine group of 4-AAP produced enamine (IV). Amine atom H3 forms an intermolecular hydrogen bond with graph set S(6) to ester carbonyl atom O2 (Fig. 1 and Table 5). The molecules pack antiparallel along the c axis, stabilized again by centrosymmtric π–π interactions between adjacent pyrazole rings [Cg···Cgiv = 4.3240 (7) Å] (Fig. 4c).
The reaction of the ketone group of ethyl 3-oxo-3-phenylpropanoate with the amine group of 4-AAP produced enamine (V). Amine atom H3 forms an intermolecular hydrogen bond with graph set S(6) to ester carbonyl atom O2, similar to (II) (Fig. 1). However, it has an additional N3—H3···O2iv hydrogen-bond interaction between neighbouring molecules, thus forming also an R22(4) hydrogen-bonded ring dimer (Fig. 4d; see Table 6 for hydrogen-bond geometry and symmetry codes). The dimers are connected via a weak C8—H8···O1v hydrogen bond along the a axis. Along the c axis, molecules are stabilized again by centrosymmtric π–π interactions, this time between adjacent benzene rings [Cg···Cgx = 4.3681 (8) Å; symmetry code: (x) -x+2, -y, -z+1] (Fig. 4d).
The reaction of the ester group of ethyl cyanoacetate with the amine group of 4-AAP produced enamine (VI). Amine atom H3 forms an intermolecular N—H···O hydrogen bond to ring carbonyl atom O1vi of a neighbouring molecule producing an R22(10) hydrogen-bonded ring dimer (Fig. 1; see Table 7 for hydrogen-bond geometry and symmetry codes). In addition, there is an intermolecular C9—H9···O2vii hydrogen bond between translationally related molecules along the b axis. A π–π interaction is observed along the a axis between pyrazole rings [Cg···Cgxi = 4.2438 (8) Å; symmetry code: (xi) -x, -y+1, -z] (Fig. 4e).
The reaction of the aldehyde group of methyl 4-formylbenzoate with the amine group of 4-AAP produced imine (VII), in contrast to the tautomerization to an enamine seen in the other compounds. Alkene atom H12 forms an intramolecular C—H···O hydrogen bond with graph set S(6) to ring carbonyl atom O1 (Fig. 1), which is different to the intramolecular hydrogen bonds observed in all the other compounds. The packing diagram of (VII) (Fig. 4f; see Table 8 for hydrogen-bond geometry and symmetry codes) shows a head-to tail arrangement and the π–π interactions between the pyrazole and benzene rings of adjacent molecules along the c axis. The centroid of the pyrazole ring (Cg1) is 3.6772 (7) Å from the centroid of the benzene ring at (-x+1/2, -y+1/2, -z+1). [No H-bond data for (VII) is included in the CIF]
Comparatively, there is similarity and some variation in the hydrogen-bonding interactions that derivatives (II)–(VII) of 4-AAP show compared to the parent compound, (I). There are four intramolecular N—H···O hydrogen bonds that form between the enamine N3 and ester carbonyl O2 atoms in (II) and (IV)–(VI). However, in (V), the pattern is slightly different due to the bifurcated nature of the H3···O2 interaction. The bifurcation of the three-centred interaction was confirmed by summing the angles around atom H3 and the sum was 356°. In the one structure that does not form the enamine tautomer, but rather the imine tautomer, i.e. (VII), an intramolecular S(6) hydrogen bond is formed, but this time a weaker C—H···O-type interaction is observed. The molecule in the crystal of (VII) is an imine because the formation of an enamine would have required the removal of the aromaticity of the benzene ring, which is unfavourable. Since the molecule is in the imine form, it does not possess the amine hydrogen-bond donor. The presence of two different aromatic-ring systems, viz. pyrazole and benzene, in all the compounds results in numerous π–π interactions. In terms of significant intermolecular interactions involving weak hydrogen bonding, there are two C—H···O interactions and one C—H···π interaction in addition to the stronger N—H···O hydrogen bonds.
Compared to other derivatized structures that have the 4-aminoantipyrine backbone, there are 146 (136 neither solvated nor hydrated) structures in the CSD that all crystallize in the imine form and only six that crystallize in the enamine form. Unsurprisingly, all 136 of the imine structures have the intramolecular C—H···O S(6) hydrogen bond, as seen in (VII). Similarly, for the five unsolvated enamine structures of the original six, all have the intramolecular N—H···O hydrogen bond. However, if one adds the criteria of having a C═O carbonyl group three C atoms away, as is seen for the derivatized compounds (II)–(VII), then the number of resulting compounds without any solvent that have the imine tautomer decreases to only one. The five enamines found in the literature all contain a carbonyl group, indicating that the presence of a second carbonyl group favours the formation of an enamine over an imine.
For all compounds, data collection: APEX3 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
C11H13N3O | Dx = 1.321 Mg m−3 |
Mr = 203.24 | Mo Kα radiation, λ = 0.71073 Å |
Hexagonal, P61 | Cell parameters from 5670 reflections |
Hall symbol: P 61 | θ = 3.2–25.2° |
a = 7.4519 (1) Å | µ = 0.09 mm−1 |
c = 31.8705 (7) Å | T = 173 K |
V = 1532.69 (5) Å3 | Prism, colourless |
Z = 6 | 0.45 × 0.18 × 0.15 mm |
F(000) = 648 |
Bruker D8 Venture Photon CMOS diffractometer | 2353 reflections with I > 2σ(I) |
ω scans | Rint = 0.031 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.0°, θmin = 1.3° |
Tmin = 0.95, Tmax = 0.96 | h = −9→9 |
13962 measured reflections | k = −9→9 |
2455 independent reflections | l = −42→42 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0536P)2 + 0.0558P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.033 | (Δ/σ)max = 0.026 |
wR(F2) = 0.083 | Δρmax = 0.16 e Å−3 |
S = 1.07 | Δρmin = −0.15 e Å−3 |
2455 reflections | Absolute structure: Flack x determined using 1076 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013). |
147 parameters | Absolute structure parameter: 0.2 (10) |
1 restraint |
C11H13N3O | Z = 6 |
Mr = 203.24 | Mo Kα radiation |
Hexagonal, P61 | µ = 0.09 mm−1 |
a = 7.4519 (1) Å | T = 173 K |
c = 31.8705 (7) Å | 0.45 × 0.18 × 0.15 mm |
V = 1532.69 (5) Å3 |
Bruker D8 Venture Photon CMOS diffractometer | 2455 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2353 reflections with I > 2σ(I) |
Tmin = 0.95, Tmax = 0.96 | Rint = 0.031 |
13962 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.083 | Δρmax = 0.16 e Å−3 |
S = 1.07 | Δρmin = −0.15 e Å−3 |
2455 reflections | Absolute structure: Flack x determined using 1076 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013). |
147 parameters | Absolute structure parameter: 0.2 (10) |
1 restraint |
Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6930 (4) | 0.2346 (4) | 0.15103 (7) | 0.0282 (5) | |
C2 | 0.6318 (4) | 0.1598 (4) | 0.19357 (8) | 0.0305 (5) | |
C3 | 0.4930 (4) | 0.2136 (4) | 0.20641 (7) | 0.0291 (5) | |
C4 | 0.3883 (4) | 0.1794 (4) | 0.24802 (8) | 0.0384 (6) | |
H4A | 0.4364 | 0.1081 | 0.2668 | 0.058* | |
H4B | 0.2379 | 0.0944 | 0.2443 | 0.058* | |
H4C | 0.4218 | 0.3133 | 0.2602 | 0.058* | |
C5 | 0.2424 (4) | 0.2541 (4) | 0.16340 (9) | 0.0355 (5) | |
H5A | 0.2387 | 0.3398 | 0.1405 | 0.053* | |
H5B | 0.1676 | 0.2648 | 0.1877 | 0.053* | |
H5C | 0.1768 | 0.1094 | 0.1542 | 0.053* | |
C6 | 0.6124 (4) | 0.4585 (4) | 0.10609 (7) | 0.0271 (5) | |
C7 | 0.6249 (4) | 0.6488 (4) | 0.11171 (9) | 0.0332 (5) | |
H7 | 0.6065 | 0.6903 | 0.1388 | 0.04* | |
C8 | 0.6649 (4) | 0.7790 (4) | 0.07719 (10) | 0.0403 (6) | |
H8 | 0.6741 | 0.91 | 0.0808 | 0.048* | |
C9 | 0.6909 (4) | 0.7174 (5) | 0.03793 (9) | 0.0437 (7) | |
H9 | 0.7174 | 0.8059 | 0.0145 | 0.052* | |
C10 | 0.6784 (4) | 0.5272 (5) | 0.03254 (8) | 0.0395 (6) | |
H10 | 0.6986 | 0.4867 | 0.0055 | 0.047* | |
C11 | 0.6369 (4) | 0.3960 (4) | 0.06634 (7) | 0.0319 (5) | |
H11 | 0.625 | 0.2641 | 0.0625 | 0.038* | |
N1 | 0.5751 (3) | 0.3231 (3) | 0.14030 (6) | 0.0280 (4) | |
N2 | 0.4599 (3) | 0.3271 (4) | 0.17519 (6) | 0.0291 (4) | |
N3 | 0.7274 (4) | 0.0677 (5) | 0.21505 (9) | 0.0508 (7) | |
H3A | 0.675 (5) | −0.001 (5) | 0.2376 (11) | 0.036 (8)* | |
H3B | 0.797 (6) | 0.040 (5) | 0.2010 (11) | 0.042 (9)* | |
O1 | 0.8267 (3) | 0.2302 (3) | 0.12882 (6) | 0.0356 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0287 (11) | 0.0295 (11) | 0.0257 (10) | 0.0140 (9) | 0.0007 (9) | 0.0023 (9) |
C2 | 0.0296 (12) | 0.0312 (11) | 0.0265 (11) | 0.0121 (10) | 0.0026 (9) | 0.0047 (9) |
C3 | 0.0280 (10) | 0.0294 (10) | 0.0231 (10) | 0.0093 (9) | 0.0018 (9) | 0.0005 (9) |
C4 | 0.0437 (14) | 0.0404 (14) | 0.0260 (12) | 0.0172 (11) | 0.0086 (11) | 0.0020 (11) |
C5 | 0.0274 (12) | 0.0381 (13) | 0.0403 (12) | 0.0159 (11) | 0.0031 (10) | −0.0030 (12) |
C6 | 0.0222 (10) | 0.0326 (12) | 0.0254 (10) | 0.0130 (9) | −0.0011 (9) | 0.0018 (9) |
C7 | 0.0303 (11) | 0.0365 (13) | 0.0354 (12) | 0.0187 (11) | −0.0018 (10) | 0.0009 (10) |
C8 | 0.0312 (12) | 0.0366 (13) | 0.0546 (16) | 0.0181 (11) | −0.0011 (12) | 0.0111 (13) |
C9 | 0.0352 (13) | 0.0501 (17) | 0.0418 (14) | 0.0184 (13) | −0.0011 (13) | 0.0200 (13) |
C10 | 0.0365 (14) | 0.0532 (16) | 0.0260 (11) | 0.0203 (12) | −0.0026 (11) | 0.0054 (12) |
C11 | 0.0308 (11) | 0.0364 (12) | 0.0270 (11) | 0.0156 (10) | −0.0032 (10) | 0.0012 (10) |
N1 | 0.0305 (10) | 0.0345 (10) | 0.0225 (8) | 0.0189 (8) | 0.0030 (7) | 0.0025 (8) |
N2 | 0.0288 (10) | 0.0324 (11) | 0.0249 (9) | 0.0143 (8) | 0.0047 (7) | 0.0010 (8) |
N3 | 0.0520 (15) | 0.0734 (19) | 0.0419 (14) | 0.0425 (15) | 0.0166 (13) | 0.0307 (15) |
O1 | 0.0382 (10) | 0.0463 (10) | 0.0307 (9) | 0.0274 (8) | 0.0096 (8) | 0.0096 (8) |
C1—O1 | 1.236 (3) | C6—C11 | 1.393 (3) |
C1—N1 | 1.380 (3) | C6—N1 | 1.416 (3) |
C1—C2 | 1.450 (3) | C7—C8 | 1.397 (4) |
C2—C3 | 1.346 (3) | C7—H7 | 0.95 |
C2—N3 | 1.391 (4) | C8—C9 | 1.380 (5) |
C3—N2 | 1.405 (3) | C8—H8 | 0.95 |
C3—C4 | 1.495 (3) | C9—C10 | 1.384 (5) |
C4—H4A | 0.98 | C9—H9 | 0.95 |
C4—H4B | 0.98 | C10—C11 | 1.382 (4) |
C4—H4C | 0.98 | C10—H10 | 0.95 |
C5—N2 | 1.477 (3) | C11—H11 | 0.95 |
C5—H5A | 0.98 | N1—N2 | 1.414 (3) |
C5—H5B | 0.98 | N3—H3A | 0.86 (4) |
C5—H5C | 0.98 | N3—H3B | 0.79 (4) |
C6—C7 | 1.385 (4) | ||
O1—C1—N1 | 125.8 (2) | C6—C7—C8 | 119.4 (3) |
O1—C1—C2 | 128.9 (2) | C6—C7—H7 | 120.3 |
N1—C1—C2 | 105.22 (19) | C8—C7—H7 | 120.3 |
C3—C2—N3 | 131.0 (2) | C9—C8—C7 | 120.0 (3) |
C3—C2—C1 | 108.1 (2) | C9—C8—H8 | 120 |
N3—C2—C1 | 120.6 (2) | C7—C8—H8 | 120 |
C2—C3—N2 | 110.87 (19) | C8—C9—C10 | 120.3 (2) |
C2—C3—C4 | 129.2 (2) | C8—C9—H9 | 119.8 |
N2—C3—C4 | 119.8 (2) | C10—C9—H9 | 119.8 |
C3—C4—H4A | 109.5 | C11—C10—C9 | 120.3 (3) |
C3—C4—H4B | 109.5 | C11—C10—H10 | 119.9 |
H4A—C4—H4B | 109.5 | C9—C10—H10 | 119.9 |
C3—C4—H4C | 109.5 | C10—C11—C6 | 119.5 (2) |
H4A—C4—H4C | 109.5 | C10—C11—H11 | 120.2 |
H4B—C4—H4C | 109.5 | C6—C11—H11 | 120.2 |
N2—C5—H5A | 109.5 | C1—N1—N2 | 110.69 (18) |
N2—C5—H5B | 109.5 | C1—N1—C6 | 125.93 (19) |
H5A—C5—H5B | 109.5 | N2—N1—C6 | 119.71 (19) |
N2—C5—H5C | 109.5 | C3—N2—N1 | 104.66 (18) |
H5A—C5—H5C | 109.5 | C3—N2—C5 | 116.7 (2) |
H5B—C5—H5C | 109.5 | N1—N2—C5 | 110.97 (18) |
C7—C6—C11 | 120.5 (2) | C2—N3—H3A | 121 (2) |
C7—C6—N1 | 121.2 (2) | C2—N3—H3B | 115 (2) |
C11—C6—N1 | 118.3 (2) | H3A—N3—H3B | 119 (3) |
O1—C1—C2—C3 | 174.7 (3) | O1—C1—N1—N2 | −171.4 (2) |
N1—C1—C2—C3 | −2.7 (3) | C2—C1—N1—N2 | 6.1 (3) |
O1—C1—C2—N3 | −0.1 (4) | O1—C1—N1—C6 | −13.3 (4) |
N1—C1—C2—N3 | −177.5 (2) | C2—C1—N1—C6 | 164.3 (2) |
N3—C2—C3—N2 | 172.3 (3) | C7—C6—N1—C1 | −127.3 (3) |
C1—C2—C3—N2 | −1.7 (3) | C11—C6—N1—C1 | 52.5 (3) |
N3—C2—C3—C4 | −3.7 (5) | C7—C6—N1—N2 | 29.0 (3) |
C1—C2—C3—C4 | −177.8 (3) | C11—C6—N1—N2 | −151.1 (2) |
C11—C6—C7—C8 | −0.8 (4) | C2—C3—N2—N1 | 5.3 (3) |
N1—C6—C7—C8 | 179.1 (2) | C4—C3—N2—N1 | −178.2 (2) |
C6—C7—C8—C9 | 0.2 (4) | C2—C3—N2—C5 | 128.4 (2) |
C7—C8—C9—C10 | −0.3 (4) | C4—C3—N2—C5 | −55.1 (3) |
C8—C9—C10—C11 | 0.9 (4) | C1—N1—N2—C3 | −7.1 (3) |
C9—C10—C11—C6 | −1.5 (4) | C6—N1—N2—C3 | −166.8 (2) |
C7—C6—C11—C10 | 1.4 (4) | C1—N1—N2—C5 | −133.8 (2) |
N1—C6—C11—C10 | −178.4 (2) | C6—N1—N2—C5 | 66.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1i | 0.86 (4) | 2.15 (4) | 2.999 (3) | 170 (3) |
Symmetry code: (i) x−y, x−1, z+1/6. |
C16H19N3O3 | F(000) = 640 |
Mr = 301.34 | Dx = 1.312 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6999 reflections |
a = 11.2061 (14) Å | θ = 3.3–28.3° |
b = 7.4638 (8) Å | µ = 0.09 mm−1 |
c = 19.044 (2) Å | T = 173 K |
β = 106.655 (4)° | Plate, colourless |
V = 1526.0 (3) Å3 | 0.42 × 0.33 × 0.13 mm |
Z = 4 |
Bruker D8 Venture Photon diffractometer | 3114 reflections with I > 2σ(I) |
ω scans | Rint = 0.018 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.0°, θmin = 3.5° |
Tmin = 0.96, Tmax = 0.99 | h = −14→14 |
12126 measured reflections | k = −9→8 |
3670 independent reflections | l = −23→25 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0562P)2 + 0.4578P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.108 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.32 e Å−3 |
3670 reflections | Δρmin = −0.25 e Å−3 |
207 parameters |
C16H19N3O3 | V = 1526.0 (3) Å3 |
Mr = 301.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.2061 (14) Å | µ = 0.09 mm−1 |
b = 7.4638 (8) Å | T = 173 K |
c = 19.044 (2) Å | 0.42 × 0.33 × 0.13 mm |
β = 106.655 (4)° |
Bruker D8 Venture Photon diffractometer | 3670 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3114 reflections with I > 2σ(I) |
Tmin = 0.96, Tmax = 0.99 | Rint = 0.018 |
12126 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.32 e Å−3 |
3670 reflections | Δρmin = −0.25 e Å−3 |
207 parameters |
Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.33084 (10) | 0.54325 (15) | 0.48152 (6) | 0.0223 (2) | |
C2 | 0.27364 (10) | 0.42379 (15) | 0.42209 (6) | 0.0222 (2) | |
C3 | 0.27806 (10) | 0.25393 (15) | 0.44904 (6) | 0.0215 (2) | |
C4 | 0.23794 (12) | 0.08445 (16) | 0.40829 (7) | 0.0300 (3) | |
H4A | 0.1794 | 0.1114 | 0.3604 | 0.045* | |
H4B | 0.1971 | 0.0077 | 0.4362 | 0.045* | |
H4C | 0.3108 | 0.0224 | 0.4014 | 0.045* | |
C5 | 0.40900 (12) | 0.11438 (15) | 0.56482 (6) | 0.0274 (3) | |
H5A | 0.3791 | −0.0026 | 0.5436 | 0.041* | |
H5B | 0.4079 | 0.1176 | 0.6161 | 0.041* | |
H5C | 0.4943 | 0.1336 | 0.5624 | 0.041* | |
C6 | 0.36757 (10) | 0.49332 (14) | 0.61445 (6) | 0.0210 (2) | |
C7 | 0.28437 (11) | 0.42183 (16) | 0.64849 (6) | 0.0258 (2) | |
H7 | 0.2311 | 0.3258 | 0.6264 | 0.031* | |
C8 | 0.27954 (12) | 0.49164 (18) | 0.71511 (7) | 0.0310 (3) | |
H8 | 0.223 | 0.4426 | 0.7388 | 0.037* | |
C9 | 0.35629 (12) | 0.63190 (17) | 0.74739 (7) | 0.0311 (3) | |
H9 | 0.3514 | 0.6807 | 0.7926 | 0.037* | |
C10 | 0.44014 (12) | 0.70079 (17) | 0.71360 (7) | 0.0320 (3) | |
H10 | 0.4935 | 0.7964 | 0.736 | 0.038* | |
C11 | 0.44716 (11) | 0.63159 (16) | 0.64722 (7) | 0.0271 (3) | |
H11 | 0.5057 | 0.6783 | 0.6245 | 0.032* | |
C12 | 0.11810 (10) | 0.58614 (15) | 0.32668 (6) | 0.0229 (2) | |
C13 | 0.05629 (12) | 0.64069 (17) | 0.38326 (7) | 0.0295 (3) | |
H13A | 0.0234 | 0.5343 | 0.4014 | 0.044* | |
H13B | −0.0121 | 0.7235 | 0.3614 | 0.044* | |
H13C | 0.1171 | 0.7 | 0.424 | 0.044* | |
C14 | 0.07240 (11) | 0.64379 (16) | 0.25596 (6) | 0.0255 (2) | |
H14 | 0.0037 | 0.724 | 0.2444 | 0.031* | |
C15 | 0.12353 (11) | 0.58856 (16) | 0.19846 (6) | 0.0263 (3) | |
C16 | 0.11845 (15) | 0.6344 (2) | 0.07489 (7) | 0.0453 (4) | |
H16A | 0.204 | 0.6798 | 0.0868 | 0.068* | |
H16B | 0.0677 | 0.6926 | 0.0302 | 0.068* | |
H16C | 0.1185 | 0.5046 | 0.0671 | 0.068* | |
N1 | 0.36827 (9) | 0.43209 (12) | 0.54355 (5) | 0.0218 (2) | |
N2 | 0.32779 (9) | 0.25576 (12) | 0.52354 (5) | 0.0216 (2) | |
N3 | 0.21884 (10) | 0.47652 (13) | 0.34857 (5) | 0.0253 (2) | |
H3 | 0.2528 (14) | 0.447 (2) | 0.3147 (9) | 0.035 (4)* | |
O1 | 0.34267 (8) | 0.70732 (11) | 0.48366 (5) | 0.0302 (2) | |
O2 | 0.20659 (9) | 0.47876 (12) | 0.20326 (5) | 0.0332 (2) | |
O3 | 0.06747 (9) | 0.67266 (14) | 0.13427 (5) | 0.0355 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0243 (5) | 0.0195 (5) | 0.0241 (5) | 0.0012 (4) | 0.0086 (4) | 0.0031 (4) |
C2 | 0.0260 (5) | 0.0209 (5) | 0.0202 (5) | 0.0036 (4) | 0.0073 (4) | 0.0026 (4) |
C3 | 0.0229 (5) | 0.0204 (5) | 0.0212 (5) | 0.0033 (4) | 0.0063 (4) | 0.0003 (4) |
C4 | 0.0391 (7) | 0.0209 (5) | 0.0253 (6) | 0.0030 (5) | 0.0015 (5) | −0.0028 (4) |
C5 | 0.0337 (6) | 0.0195 (5) | 0.0260 (6) | 0.0054 (5) | 0.0035 (5) | 0.0041 (4) |
C6 | 0.0216 (5) | 0.0188 (5) | 0.0203 (5) | 0.0033 (4) | 0.0026 (4) | 0.0004 (4) |
C7 | 0.0251 (5) | 0.0259 (6) | 0.0252 (6) | −0.0028 (4) | 0.0054 (4) | −0.0021 (4) |
C8 | 0.0312 (6) | 0.0364 (7) | 0.0273 (6) | 0.0017 (5) | 0.0111 (5) | 0.0001 (5) |
C9 | 0.0352 (6) | 0.0337 (6) | 0.0217 (6) | 0.0075 (5) | 0.0036 (5) | −0.0046 (5) |
C10 | 0.0334 (6) | 0.0281 (6) | 0.0288 (6) | −0.0026 (5) | −0.0002 (5) | −0.0064 (5) |
C11 | 0.0254 (6) | 0.0255 (6) | 0.0289 (6) | −0.0031 (4) | 0.0056 (5) | −0.0014 (5) |
C12 | 0.0247 (5) | 0.0184 (5) | 0.0248 (6) | −0.0021 (4) | 0.0056 (4) | 0.0002 (4) |
C13 | 0.0282 (6) | 0.0330 (6) | 0.0280 (6) | 0.0030 (5) | 0.0094 (5) | −0.0002 (5) |
C14 | 0.0245 (5) | 0.0240 (5) | 0.0256 (6) | 0.0018 (4) | 0.0037 (4) | 0.0035 (4) |
C15 | 0.0289 (6) | 0.0250 (6) | 0.0220 (6) | −0.0058 (5) | 0.0026 (4) | 0.0021 (4) |
C16 | 0.0520 (9) | 0.0604 (10) | 0.0236 (6) | −0.0095 (7) | 0.0108 (6) | 0.0056 (6) |
N1 | 0.0281 (5) | 0.0153 (4) | 0.0215 (5) | −0.0012 (4) | 0.0065 (4) | −0.0003 (3) |
N2 | 0.0292 (5) | 0.0146 (4) | 0.0198 (4) | 0.0006 (4) | 0.0048 (4) | 0.0006 (3) |
N3 | 0.0329 (5) | 0.0249 (5) | 0.0190 (5) | 0.0084 (4) | 0.0087 (4) | 0.0040 (4) |
O1 | 0.0402 (5) | 0.0173 (4) | 0.0325 (5) | −0.0024 (3) | 0.0092 (4) | 0.0034 (3) |
O2 | 0.0425 (5) | 0.0301 (5) | 0.0275 (4) | 0.0053 (4) | 0.0111 (4) | −0.0002 (4) |
O3 | 0.0349 (5) | 0.0464 (6) | 0.0231 (4) | −0.0012 (4) | 0.0048 (4) | 0.0098 (4) |
C1—O1 | 1.2312 (14) | C9—C10 | 1.3812 (19) |
C1—N1 | 1.4057 (14) | C9—H9 | 0.95 |
C1—C2 | 1.4390 (16) | C10—C11 | 1.3887 (18) |
C2—C3 | 1.3633 (15) | C10—H10 | 0.95 |
C2—N3 | 1.4141 (14) | C11—H11 | 0.95 |
C3—N2 | 1.3677 (14) | C12—N3 | 1.3593 (15) |
C3—C4 | 1.4848 (16) | C12—C14 | 1.3659 (16) |
C4—H4A | 0.98 | C12—C13 | 1.4948 (16) |
C4—H4B | 0.98 | C13—H13A | 0.98 |
C4—H4C | 0.98 | C13—H13B | 0.98 |
C5—N2 | 1.4662 (14) | C13—H13C | 0.98 |
C5—H5A | 0.98 | C14—C15 | 1.4343 (17) |
C5—H5B | 0.98 | C14—H14 | 0.95 |
C5—H5C | 0.98 | C15—O2 | 1.2237 (15) |
C6—C7 | 1.3860 (16) | C15—O3 | 1.3575 (14) |
C6—C11 | 1.3895 (16) | C16—O3 | 1.4343 (17) |
C6—N1 | 1.4276 (14) | C16—H16A | 0.98 |
C7—C8 | 1.3868 (17) | C16—H16B | 0.98 |
C7—H7 | 0.95 | C16—H16C | 0.98 |
C8—C9 | 1.3822 (18) | N1—N2 | 1.4086 (12) |
C8—H8 | 0.95 | N3—H3 | 0.865 (15) |
O1—C1—N1 | 123.77 (10) | C11—C10—H10 | 119.7 |
O1—C1—C2 | 131.43 (11) | C10—C11—C6 | 119.24 (11) |
N1—C1—C2 | 104.70 (9) | C10—C11—H11 | 120.4 |
C3—C2—N3 | 126.17 (10) | C6—C11—H11 | 120.4 |
C3—C2—C1 | 108.67 (10) | N3—C12—C14 | 122.39 (11) |
N3—C2—C1 | 125.13 (10) | N3—C12—C13 | 117.29 (10) |
C2—C3—N2 | 109.96 (10) | C14—C12—C13 | 120.31 (11) |
C2—C3—C4 | 128.51 (10) | C12—C13—H13A | 109.5 |
N2—C3—C4 | 121.53 (10) | C12—C13—H13B | 109.5 |
C3—C4—H4A | 109.5 | H13A—C13—H13B | 109.5 |
C3—C4—H4B | 109.5 | C12—C13—H13C | 109.5 |
H4A—C4—H4B | 109.5 | H13A—C13—H13C | 109.5 |
C3—C4—H4C | 109.5 | H13B—C13—H13C | 109.5 |
H4A—C4—H4C | 109.5 | C12—C14—C15 | 122.91 (11) |
H4B—C4—H4C | 109.5 | C12—C14—H14 | 118.5 |
N2—C5—H5A | 109.5 | C15—C14—H14 | 118.5 |
N2—C5—H5B | 109.5 | O2—C15—O3 | 121.51 (11) |
H5A—C5—H5B | 109.5 | O2—C15—C14 | 126.67 (11) |
N2—C5—H5C | 109.5 | O3—C15—C14 | 111.82 (11) |
H5A—C5—H5C | 109.5 | O3—C16—H16A | 109.5 |
H5B—C5—H5C | 109.5 | O3—C16—H16B | 109.5 |
C7—C6—C11 | 120.47 (11) | H16A—C16—H16B | 109.5 |
C7—C6—N1 | 120.39 (10) | O3—C16—H16C | 109.5 |
C11—C6—N1 | 119.06 (10) | H16A—C16—H16C | 109.5 |
C6—C7—C8 | 119.41 (11) | H16B—C16—H16C | 109.5 |
C6—C7—H7 | 120.3 | C1—N1—N2 | 109.19 (8) |
C8—C7—H7 | 120.3 | C1—N1—C6 | 121.65 (9) |
C9—C8—C7 | 120.59 (12) | N2—N1—C6 | 117.80 (9) |
C9—C8—H8 | 119.7 | C3—N2—N1 | 107.09 (8) |
C7—C8—H8 | 119.7 | C3—N2—C5 | 123.70 (9) |
C10—C9—C8 | 119.64 (11) | N1—N2—C5 | 115.16 (9) |
C10—C9—H9 | 120.2 | C12—N3—C2 | 123.92 (10) |
C8—C9—H9 | 120.2 | C12—N3—H3 | 115.2 (10) |
C9—C10—C11 | 120.61 (12) | C2—N3—H3 | 120.6 (10) |
C9—C10—H10 | 119.7 | C15—O3—C16 | 115.58 (11) |
O1—C1—C2—C3 | −176.21 (12) | C2—C1—N1—N2 | −3.94 (11) |
N1—C1—C2—C3 | 0.18 (12) | O1—C1—N1—C6 | 30.18 (16) |
O1—C1—C2—N3 | 2.0 (2) | C2—C1—N1—C6 | −146.57 (10) |
N1—C1—C2—N3 | 178.38 (10) | C7—C6—N1—C1 | 112.10 (12) |
N3—C2—C3—N2 | −174.40 (10) | C11—C6—N1—C1 | −64.76 (14) |
C1—C2—C3—N2 | 3.78 (13) | C7—C6—N1—N2 | −27.50 (14) |
N3—C2—C3—C4 | 5.9 (2) | C11—C6—N1—N2 | 155.64 (10) |
C1—C2—C3—C4 | −175.94 (11) | C2—C3—N2—N1 | −6.19 (12) |
C11—C6—C7—C8 | 1.14 (17) | C4—C3—N2—N1 | 173.56 (10) |
N1—C6—C7—C8 | −175.67 (10) | C2—C3—N2—C5 | −143.89 (11) |
C6—C7—C8—C9 | 0.34 (18) | C4—C3—N2—C5 | 35.87 (16) |
C7—C8—C9—C10 | −1.23 (19) | C1—N1—N2—C3 | 6.29 (12) |
C8—C9—C10—C11 | 0.63 (19) | C6—N1—N2—C3 | 150.55 (9) |
C9—C10—C11—C6 | 0.83 (19) | C1—N1—N2—C5 | 148.07 (10) |
C7—C6—C11—C10 | −1.73 (17) | C6—N1—N2—C5 | −67.67 (12) |
N1—C6—C11—C10 | 175.13 (11) | C14—C12—N3—C2 | 175.65 (11) |
N3—C12—C14—C15 | 2.42 (18) | C13—C12—N3—C2 | −5.27 (17) |
C13—C12—C14—C15 | −176.63 (11) | C3—C2—N3—C12 | 115.01 (14) |
C12—C14—C15—O2 | 4.5 (2) | C1—C2—N3—C12 | −62.89 (16) |
C12—C14—C15—O3 | −176.07 (11) | O2—C15—O3—C16 | −4.56 (17) |
O1—C1—N1—N2 | 172.80 (10) | C14—C15—O3—C16 | 176.01 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.865 (15) | 2.048 (16) | 2.7312 (13) | 135 (1) |
C17H21N3O3 | F(000) = 672 |
Mr = 315.37 | Dx = 1.283 Mg m−3 Dm = 0 Mg m−3 Dm measured by ? |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9952 reflections |
a = 13.427 (2) Å | θ = 3.4–28.3° |
b = 10.1086 (14) Å | µ = 0.09 mm−1 |
c = 12.2801 (18) Å | T = 173 K |
β = 101.690 (5)° | Block, brown |
V = 1632.2 (4) Å3 | 0.42 × 0.39 × 0.31 mm |
Z = 4 |
Bruker D8 Venture Photon diffractometer | 3494 reflections with I > 2σ(I) |
ω scans | Rint = 0.021 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.0°, θmin = 3.4° |
Tmin = 0.96, Tmax = 0.97 | h = −17→17 |
20796 measured reflections | k = −13→13 |
3921 independent reflections | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0661P)2 + 0.4416P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.115 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.30 e Å−3 |
3921 reflections | Δρmin = −0.26 e Å−3 |
216 parameters |
C17H21N3O3 | V = 1632.2 (4) Å3 |
Mr = 315.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.427 (2) Å | µ = 0.09 mm−1 |
b = 10.1086 (14) Å | T = 173 K |
c = 12.2801 (18) Å | 0.42 × 0.39 × 0.31 mm |
β = 101.690 (5)° |
Bruker D8 Venture Photon diffractometer | 3921 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3494 reflections with I > 2σ(I) |
Tmin = 0.96, Tmax = 0.97 | Rint = 0.021 |
20796 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.30 e Å−3 |
3921 reflections | Δρmin = −0.26 e Å−3 |
216 parameters |
Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.50682 (8) | 0.24189 (10) | 0.49565 (8) | 0.0220 (2) | |
C2 | 0.56615 (8) | 0.34047 (10) | 0.45208 (8) | 0.0224 (2) | |
C3 | 0.50318 (8) | 0.41389 (10) | 0.37465 (8) | 0.0230 (2) | |
C4 | 0.52683 (9) | 0.52616 (11) | 0.30537 (10) | 0.0307 (2) | |
H4A | 0.5958 | 0.5584 | 0.3353 | 0.046* | |
H4B | 0.4779 | 0.5978 | 0.3066 | 0.046* | |
H4C | 0.5223 | 0.496 | 0.2287 | 0.046* | |
C5 | 0.33522 (9) | 0.36253 (12) | 0.25646 (9) | 0.0298 (2) | |
H5A | 0.3317 | 0.449 | 0.2197 | 0.045* | |
H5B | 0.2673 | 0.3373 | 0.267 | 0.045* | |
H5C | 0.3601 | 0.2962 | 0.2102 | 0.045* | |
C6 | 0.31891 (8) | 0.20442 (10) | 0.45872 (8) | 0.0218 (2) | |
C7 | 0.24395 (8) | 0.28769 (11) | 0.48285 (9) | 0.0262 (2) | |
H7 | 0.2516 | 0.381 | 0.48 | 0.031* | |
C8 | 0.15768 (9) | 0.23323 (13) | 0.51115 (10) | 0.0326 (3) | |
H8 | 0.1057 | 0.2893 | 0.5273 | 0.039* | |
C9 | 0.14749 (9) | 0.09698 (14) | 0.51584 (10) | 0.0357 (3) | |
H9 | 0.0889 | 0.0598 | 0.5361 | 0.043* | |
C10 | 0.22245 (10) | 0.01499 (12) | 0.49106 (10) | 0.0342 (3) | |
H10 | 0.2146 | −0.0783 | 0.4939 | 0.041* | |
C11 | 0.30883 (9) | 0.06761 (11) | 0.46209 (9) | 0.0273 (2) | |
H11 | 0.3602 | 0.0113 | 0.4449 | 0.033* | |
C12 | 0.74722 (8) | 0.34228 (10) | 0.44013 (9) | 0.0248 (2) | |
C13 | 0.72015 (10) | 0.29611 (16) | 0.32186 (11) | 0.0412 (3) | |
H13A | 0.6707 | 0.2239 | 0.3158 | 0.062* | |
H13B | 0.7815 | 0.2646 | 0.2984 | 0.062* | |
H13C | 0.6905 | 0.3697 | 0.2741 | 0.062* | |
C14 | 0.84661 (8) | 0.36475 (11) | 0.48936 (9) | 0.0265 (2) | |
H14 | 0.8971 | 0.353 | 0.4461 | 0.032* | |
C15 | 0.87833 (8) | 0.40522 (10) | 0.60321 (9) | 0.0235 (2) | |
C16 | 1.02030 (9) | 0.46559 (14) | 0.74458 (10) | 0.0371 (3) | |
H16A | 1.0937 | 0.4438 | 0.7636 | 0.044* | |
H16B | 0.9857 | 0.4142 | 0.7947 | 0.044* | |
C17 | 1.00661 (11) | 0.61014 (14) | 0.76352 (12) | 0.0419 (3) | |
H17A | 1.0376 | 0.6615 | 0.7114 | 0.063* | |
H17B | 1.0394 | 0.633 | 0.8399 | 0.063* | |
H17C | 0.9339 | 0.6306 | 0.7517 | 0.063* | |
N1 | 0.40925 (7) | 0.25677 (9) | 0.43186 (7) | 0.0237 (2) | |
N2 | 0.40470 (7) | 0.37017 (9) | 0.36466 (7) | 0.0229 (2) | |
N3 | 0.67072 (7) | 0.35975 (10) | 0.49527 (8) | 0.0250 (2) | |
H3 | 0.6905 (13) | 0.3796 (17) | 0.5667 (15) | 0.049 (4)* | |
O1 | 0.53027 (6) | 0.16475 (8) | 0.57443 (6) | 0.02857 (19) | |
O2 | 0.82303 (6) | 0.41981 (8) | 0.67041 (6) | 0.02946 (19) | |
O3 | 0.97998 (6) | 0.42703 (9) | 0.63075 (7) | 0.0325 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0195 (5) | 0.0245 (5) | 0.0215 (4) | 0.0030 (4) | 0.0030 (4) | −0.0016 (4) |
C2 | 0.0207 (5) | 0.0253 (5) | 0.0215 (4) | 0.0001 (4) | 0.0048 (4) | −0.0035 (4) |
C3 | 0.0244 (5) | 0.0239 (5) | 0.0214 (5) | 0.0012 (4) | 0.0066 (4) | −0.0027 (4) |
C4 | 0.0361 (6) | 0.0269 (5) | 0.0300 (5) | −0.0004 (4) | 0.0093 (5) | 0.0033 (4) |
C5 | 0.0282 (6) | 0.0387 (6) | 0.0201 (5) | 0.0037 (4) | −0.0009 (4) | 0.0012 (4) |
C6 | 0.0187 (5) | 0.0265 (5) | 0.0191 (4) | 0.0003 (4) | 0.0011 (4) | 0.0006 (4) |
C7 | 0.0238 (5) | 0.0271 (5) | 0.0267 (5) | 0.0033 (4) | 0.0028 (4) | −0.0004 (4) |
C8 | 0.0209 (5) | 0.0469 (7) | 0.0299 (6) | 0.0038 (5) | 0.0049 (4) | −0.0014 (5) |
C9 | 0.0252 (6) | 0.0515 (7) | 0.0295 (6) | −0.0124 (5) | 0.0030 (4) | 0.0033 (5) |
C10 | 0.0366 (6) | 0.0303 (6) | 0.0326 (6) | −0.0097 (5) | −0.0007 (5) | 0.0026 (5) |
C11 | 0.0275 (5) | 0.0261 (5) | 0.0264 (5) | 0.0018 (4) | 0.0011 (4) | −0.0011 (4) |
C12 | 0.0247 (5) | 0.0247 (5) | 0.0256 (5) | 0.0008 (4) | 0.0062 (4) | −0.0040 (4) |
C13 | 0.0280 (6) | 0.0633 (9) | 0.0321 (6) | 0.0019 (6) | 0.0058 (5) | −0.0218 (6) |
C14 | 0.0222 (5) | 0.0315 (5) | 0.0268 (5) | 0.0000 (4) | 0.0074 (4) | −0.0044 (4) |
C15 | 0.0217 (5) | 0.0218 (5) | 0.0264 (5) | 0.0001 (4) | 0.0033 (4) | 0.0020 (4) |
C16 | 0.0283 (6) | 0.0457 (7) | 0.0326 (6) | −0.0014 (5) | −0.0047 (5) | −0.0058 (5) |
C17 | 0.0436 (7) | 0.0443 (7) | 0.0383 (7) | −0.0091 (6) | 0.0095 (6) | −0.0053 (6) |
N1 | 0.0194 (4) | 0.0267 (4) | 0.0242 (4) | 0.0026 (3) | 0.0025 (3) | 0.0058 (3) |
N2 | 0.0233 (4) | 0.0255 (4) | 0.0194 (4) | 0.0023 (3) | 0.0028 (3) | 0.0034 (3) |
N3 | 0.0198 (4) | 0.0335 (5) | 0.0215 (4) | −0.0023 (3) | 0.0035 (3) | −0.0047 (3) |
O1 | 0.0248 (4) | 0.0322 (4) | 0.0275 (4) | 0.0056 (3) | 0.0024 (3) | 0.0074 (3) |
O2 | 0.0265 (4) | 0.0387 (5) | 0.0237 (4) | −0.0019 (3) | 0.0061 (3) | 0.0003 (3) |
O3 | 0.0213 (4) | 0.0433 (5) | 0.0315 (4) | −0.0017 (3) | 0.0018 (3) | −0.0070 (3) |
C1—O1 | 1.2328 (13) | C10—C11 | 1.3864 (17) |
C1—N1 | 1.3916 (13) | C10—H10 | 0.95 |
C1—C2 | 1.4446 (14) | C11—H11 | 0.95 |
C2—C3 | 1.3579 (15) | C12—N3 | 1.3515 (14) |
C2—N3 | 1.4102 (14) | C12—C14 | 1.3679 (16) |
C3—N2 | 1.3759 (14) | C12—C13 | 1.4985 (15) |
C3—C4 | 1.4906 (15) | C13—H13A | 0.98 |
C4—H4A | 0.98 | C13—H13B | 0.98 |
C4—H4B | 0.98 | C13—H13C | 0.98 |
C4—H4C | 0.98 | C14—C15 | 1.4360 (15) |
C5—N2 | 1.4627 (13) | C14—H14 | 0.95 |
C5—H5A | 0.98 | C15—O2 | 1.2258 (13) |
C5—H5B | 0.98 | C15—O3 | 1.3559 (13) |
C5—H5C | 0.98 | C16—O3 | 1.4464 (14) |
C6—C7 | 1.3893 (15) | C16—C17 | 1.4967 (19) |
C6—C11 | 1.3910 (15) | C16—H16A | 0.99 |
C6—N1 | 1.4220 (13) | C16—H16B | 0.99 |
C7—C8 | 1.3887 (16) | C17—H17A | 0.98 |
C7—H7 | 0.95 | C17—H17B | 0.98 |
C8—C9 | 1.3864 (19) | C17—H17C | 0.98 |
C8—H8 | 0.95 | N1—N2 | 1.4066 (12) |
C9—C10 | 1.3844 (19) | N3—H3 | 0.886 (18) |
C9—H9 | 0.95 | ||
O1—C1—N1 | 124.87 (10) | C6—C11—H11 | 120.6 |
O1—C1—C2 | 130.90 (10) | N3—C12—C14 | 121.96 (10) |
N1—C1—C2 | 104.11 (9) | N3—C12—C13 | 117.81 (10) |
C3—C2—N3 | 128.24 (10) | C14—C12—C13 | 120.22 (10) |
C3—C2—C1 | 108.94 (9) | C12—C13—H13A | 109.5 |
N3—C2—C1 | 122.53 (9) | C12—C13—H13B | 109.5 |
C2—C3—N2 | 109.74 (9) | H13A—C13—H13B | 109.5 |
C2—C3—C4 | 129.89 (10) | C12—C13—H13C | 109.5 |
N2—C3—C4 | 120.37 (9) | H13A—C13—H13C | 109.5 |
C3—C4—H4A | 109.5 | H13B—C13—H13C | 109.5 |
C3—C4—H4B | 109.5 | C12—C14—C15 | 123.23 (10) |
H4A—C4—H4B | 109.5 | C12—C14—H14 | 118.4 |
C3—C4—H4C | 109.5 | C15—C14—H14 | 118.4 |
H4A—C4—H4C | 109.5 | O2—C15—O3 | 121.93 (10) |
H4B—C4—H4C | 109.5 | O2—C15—C14 | 126.09 (10) |
N2—C5—H5A | 109.5 | O3—C15—C14 | 111.98 (9) |
N2—C5—H5B | 109.5 | O3—C16—C17 | 112.31 (11) |
H5A—C5—H5B | 109.5 | O3—C16—H16A | 109.1 |
N2—C5—H5C | 109.5 | C17—C16—H16A | 109.1 |
H5A—C5—H5C | 109.5 | O3—C16—H16B | 109.1 |
H5B—C5—H5C | 109.5 | C17—C16—H16B | 109.1 |
C7—C6—C11 | 121.12 (10) | H16A—C16—H16B | 107.9 |
C7—C6—N1 | 120.86 (10) | C16—C17—H17A | 109.5 |
C11—C6—N1 | 118.00 (9) | C16—C17—H17B | 109.5 |
C8—C7—C6 | 119.36 (11) | H17A—C17—H17B | 109.5 |
C8—C7—H7 | 120.3 | C16—C17—H17C | 109.5 |
C6—C7—H7 | 120.3 | H17A—C17—H17C | 109.5 |
C9—C8—C7 | 119.90 (11) | H17B—C17—H17C | 109.5 |
C9—C8—H8 | 120 | C1—N1—N2 | 110.02 (8) |
C7—C8—H8 | 120 | C1—N1—C6 | 125.40 (9) |
C10—C9—C8 | 120.22 (11) | N2—N1—C6 | 120.11 (8) |
C10—C9—H9 | 119.9 | C3—N2—N1 | 106.42 (8) |
C8—C9—H9 | 119.9 | C3—N2—C5 | 121.50 (9) |
C9—C10—C11 | 120.66 (11) | N1—N2—C5 | 115.71 (9) |
C9—C10—H10 | 119.7 | C12—N3—C2 | 126.39 (9) |
C11—C10—H10 | 119.7 | C12—N3—H3 | 114.8 (11) |
C10—C11—C6 | 118.73 (10) | C2—N3—H3 | 118.6 (11) |
C10—C11—H11 | 120.6 | C15—O3—C16 | 116.46 (9) |
O1—C1—C2—C3 | −171.19 (11) | O1—C1—N1—C6 | 11.97 (17) |
N1—C1—C2—C3 | 4.94 (11) | C2—C1—N1—C6 | −164.46 (9) |
O1—C1—C2—N3 | 3.12 (17) | C7—C6—N1—C1 | 114.34 (12) |
N1—C1—C2—N3 | 179.25 (9) | C11—C6—N1—C1 | −64.49 (14) |
N3—C2—C3—N2 | −173.49 (9) | C7—C6—N1—N2 | −39.49 (14) |
C1—C2—C3—N2 | 0.40 (11) | C11—C6—N1—N2 | 141.68 (10) |
N3—C2—C3—C4 | 6.68 (18) | C2—C3—N2—N1 | −5.57 (11) |
C1—C2—C3—C4 | −179.43 (10) | C4—C3—N2—N1 | 174.28 (9) |
C11—C6—C7—C8 | 0.22 (16) | C2—C3—N2—C5 | −140.90 (10) |
N1—C6—C7—C8 | −178.58 (9) | C4—C3—N2—C5 | 38.95 (14) |
C6—C7—C8—C9 | 0.46 (17) | C1—N1—N2—C3 | 8.90 (11) |
C7—C8—C9—C10 | −0.80 (18) | C6—N1—N2—C3 | 166.40 (9) |
C8—C9—C10—C11 | 0.47 (18) | C1—N1—N2—C5 | 147.19 (9) |
C9—C10—C11—C6 | 0.20 (17) | C6—N1—N2—C5 | −55.31 (12) |
C7—C6—C11—C10 | −0.54 (16) | C14—C12—N3—C2 | 179.44 (10) |
N1—C6—C11—C10 | 178.29 (9) | C13—C12—N3—C2 | −0.92 (17) |
N3—C12—C14—C15 | 1.55 (18) | C3—C2—N3—C12 | −69.82 (16) |
C13—C12—C14—C15 | −178.08 (11) | C1—C2—N3—C12 | 117.04 (12) |
C12—C14—C15—O2 | 2.80 (18) | O2—C15—O3—C16 | 1.37 (16) |
C12—C14—C15—O3 | −177.10 (10) | C14—C15—O3—C16 | −178.72 (10) |
O1—C1—N1—N2 | 168.01 (10) | C17—C16—O3—C15 | −81.62 (13) |
C2—C1—N1—N2 | −8.42 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.886 (18) | 2.009 (18) | 2.7192 (12) | 136 (1) |
C11—H11···O1i | 0.95 | 2.35 | 3.2829 (14) | 167 |
C8—H8···O3ii | 0.95 | 2.7 | 3.6206 (15) | 164 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z. |
C20H25N3O3 | Z = 2 |
Mr = 355.43 | F(000) = 380 |
Triclinic, P1 | Dx = 1.274 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3857 (2) Å | Cell parameters from 8186 reflections |
b = 9.2159 (3) Å | θ = 2.2–28.3° |
c = 13.7494 (4) Å | µ = 0.09 mm−1 |
α = 85.898 (1)° | T = 173 K |
β = 84.499 (1)° | Plate, colourless |
γ = 85.210 (1)° | 0.3 × 0.3 × 0.19 mm |
V = 926.40 (5) Å3 |
Bruker D8 Venture Photon diffractometer | 3628 reflections with I > 2σ(I) |
ω scans | Rint = 0.043 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.0°, θmin = 1.5° |
Tmin = 0.95, Tmax = 0.96 | h = −9→9 |
20559 measured reflections | k = −12→11 |
4466 independent reflections | l = −18→18 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0494P)2 + 0.2134P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.107 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.24 e Å−3 |
4466 reflections | Δρmin = −0.23 e Å−3 |
242 parameters |
C20H25N3O3 | γ = 85.210 (1)° |
Mr = 355.43 | V = 926.40 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3857 (2) Å | Mo Kα radiation |
b = 9.2159 (3) Å | µ = 0.09 mm−1 |
c = 13.7494 (4) Å | T = 173 K |
α = 85.898 (1)° | 0.3 × 0.3 × 0.19 mm |
β = 84.499 (1)° |
Bruker D8 Venture Photon diffractometer | 4466 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3628 reflections with I > 2σ(I) |
Tmin = 0.95, Tmax = 0.96 | Rint = 0.043 |
20559 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.24 e Å−3 |
4466 reflections | Δρmin = −0.23 e Å−3 |
242 parameters |
Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.69149 (16) | 0.77040 (13) | 0.44703 (8) | 0.0257 (2) | |
C2 | 0.56088 (16) | 0.70172 (13) | 0.39711 (8) | 0.0253 (2) | |
C3 | 0.41466 (16) | 0.67442 (12) | 0.46160 (8) | 0.0252 (2) | |
C4 | 0.24182 (17) | 0.61259 (14) | 0.44459 (9) | 0.0325 (3) | |
H4A | 0.2502 | 0.5807 | 0.3777 | 0.049* | |
H4B | 0.1402 | 0.6873 | 0.4535 | 0.049* | |
H4C | 0.2211 | 0.529 | 0.4913 | 0.049* | |
C5 | 0.29521 (17) | 0.78324 (14) | 0.61675 (9) | 0.0302 (3) | |
H5A | 0.2666 | 0.8836 | 0.5909 | 0.045* | |
H5B | 0.3322 | 0.7843 | 0.6833 | 0.045* | |
H5C | 0.187 | 0.7281 | 0.6182 | 0.045* | |
C6 | 0.70009 (16) | 0.81214 (13) | 0.62319 (8) | 0.0249 (2) | |
C7 | 0.69056 (18) | 0.71728 (13) | 0.70625 (8) | 0.0292 (3) | |
H7 | 0.6208 | 0.6348 | 0.709 | 0.035* | |
C8 | 0.78386 (19) | 0.74410 (14) | 0.78510 (9) | 0.0341 (3) | |
H8 | 0.7779 | 0.6797 | 0.8422 | 0.041* | |
C9 | 0.88554 (19) | 0.86411 (15) | 0.78110 (9) | 0.0345 (3) | |
H9 | 0.9494 | 0.8818 | 0.8353 | 0.041* | |
C10 | 0.89427 (17) | 0.95840 (14) | 0.69818 (9) | 0.0320 (3) | |
H10 | 0.9639 | 1.041 | 0.6957 | 0.038* | |
C11 | 0.80186 (17) | 0.93284 (13) | 0.61877 (9) | 0.0285 (3) | |
H11 | 0.8081 | 0.9974 | 0.5617 | 0.034* | |
C12 | 0.63541 (15) | 0.74644 (12) | 0.22002 (8) | 0.0239 (2) | |
C13 | 0.68815 (15) | 0.69490 (12) | 0.12974 (8) | 0.0236 (2) | |
C14 | 0.73716 (17) | 0.79641 (13) | 0.04140 (8) | 0.0268 (3) | |
H14A | 0.6382 | 0.8023 | −0.0028 | 0.032* | |
H14B | 0.8499 | 0.7551 | 0.0053 | 0.032* | |
C15 | 0.7664 (2) | 0.94900 (14) | 0.06831 (9) | 0.0339 (3) | |
H15A | 0.8841 | 0.9481 | 0.0974 | 0.041* | |
H15B | 0.7713 | 1.0159 | 0.0086 | 0.041* | |
C16 | 0.6127 (2) | 1.00262 (14) | 0.14074 (9) | 0.0346 (3) | |
H16A | 0.4944 | 0.9992 | 0.113 | 0.042* | |
H16B | 0.6271 | 1.105 | 0.1539 | 0.042* | |
C17 | 0.61487 (18) | 0.90701 (13) | 0.23578 (8) | 0.0292 (3) | |
H17A | 0.7169 | 0.9316 | 0.2718 | 0.035* | |
H17B | 0.4999 | 0.9291 | 0.2771 | 0.035* | |
C18 | 0.69463 (16) | 0.54040 (13) | 0.11583 (8) | 0.0253 (2) | |
C19 | 0.74116 (19) | 0.35824 (13) | 0.00053 (9) | 0.0318 (3) | |
H19A | 0.6193 | 0.3218 | 0.0185 | 0.038* | |
H19B | 0.8307 | 0.2988 | 0.0388 | 0.038* | |
C20 | 0.7937 (2) | 0.34768 (15) | −0.10745 (10) | 0.0365 (3) | |
H20A | 0.7042 | 0.407 | −0.1446 | 0.055* | |
H20B | 0.7963 | 0.2457 | −0.1238 | 0.055* | |
H20C | 0.9148 | 0.3835 | −0.1243 | 0.055* | |
N1 | 0.60598 (13) | 0.78805 (11) | 0.54063 (7) | 0.0262 (2) | |
N2 | 0.44476 (13) | 0.71398 (11) | 0.55359 (7) | 0.0256 (2) | |
N3 | 0.59282 (14) | 0.65599 (12) | 0.30077 (7) | 0.0273 (2) | |
H3 | 0.608 (2) | 0.5608 (18) | 0.2902 (11) | 0.043 (4)* | |
O1 | 0.84587 (12) | 0.80604 (10) | 0.41948 (6) | 0.0331 (2) | |
O2 | 0.66354 (13) | 0.44227 (9) | 0.17906 (6) | 0.0339 (2) | |
O3 | 0.73861 (12) | 0.50993 (9) | 0.02103 (6) | 0.0285 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0294 (6) | 0.0280 (6) | 0.0186 (5) | −0.0005 (5) | −0.0004 (4) | 0.0019 (4) |
C2 | 0.0295 (6) | 0.0264 (6) | 0.0192 (5) | −0.0004 (5) | −0.0007 (4) | 0.0004 (4) |
C3 | 0.0281 (6) | 0.0235 (5) | 0.0235 (5) | 0.0003 (5) | −0.0025 (4) | −0.0013 (4) |
C4 | 0.0302 (7) | 0.0350 (7) | 0.0330 (6) | −0.0043 (5) | −0.0030 (5) | −0.0048 (5) |
C5 | 0.0310 (6) | 0.0336 (6) | 0.0248 (6) | −0.0015 (5) | 0.0049 (5) | −0.0048 (5) |
C6 | 0.0273 (6) | 0.0282 (6) | 0.0191 (5) | −0.0024 (5) | 0.0002 (4) | −0.0031 (4) |
C7 | 0.0403 (7) | 0.0270 (6) | 0.0208 (5) | −0.0090 (5) | 0.0002 (5) | −0.0023 (4) |
C8 | 0.0487 (8) | 0.0343 (7) | 0.0200 (5) | −0.0080 (6) | −0.0041 (5) | 0.0002 (5) |
C9 | 0.0396 (7) | 0.0406 (7) | 0.0255 (6) | −0.0087 (6) | −0.0060 (5) | −0.0064 (5) |
C10 | 0.0315 (7) | 0.0335 (7) | 0.0320 (6) | −0.0109 (5) | 0.0017 (5) | −0.0048 (5) |
C11 | 0.0306 (6) | 0.0289 (6) | 0.0252 (6) | −0.0048 (5) | 0.0016 (5) | 0.0022 (5) |
C12 | 0.0230 (6) | 0.0277 (6) | 0.0207 (5) | −0.0016 (5) | −0.0029 (4) | 0.0010 (4) |
C13 | 0.0250 (6) | 0.0259 (6) | 0.0200 (5) | −0.0034 (4) | −0.0022 (4) | 0.0000 (4) |
C14 | 0.0329 (6) | 0.0278 (6) | 0.0197 (5) | −0.0048 (5) | −0.0017 (4) | −0.0002 (4) |
C15 | 0.0485 (8) | 0.0283 (6) | 0.0249 (6) | −0.0096 (6) | −0.0002 (5) | 0.0010 (5) |
C16 | 0.0519 (8) | 0.0255 (6) | 0.0257 (6) | 0.0014 (6) | −0.0043 (5) | −0.0001 (5) |
C17 | 0.0378 (7) | 0.0272 (6) | 0.0219 (5) | 0.0015 (5) | −0.0020 (5) | −0.0023 (4) |
C18 | 0.0252 (6) | 0.0288 (6) | 0.0218 (5) | −0.0020 (5) | −0.0009 (4) | −0.0015 (4) |
C19 | 0.0383 (7) | 0.0245 (6) | 0.0326 (6) | −0.0015 (5) | −0.0018 (5) | −0.0051 (5) |
C20 | 0.0421 (8) | 0.0344 (7) | 0.0333 (7) | −0.0002 (6) | −0.0021 (6) | −0.0097 (5) |
N1 | 0.0273 (5) | 0.0334 (5) | 0.0181 (4) | −0.0078 (4) | 0.0008 (4) | −0.0008 (4) |
N2 | 0.0250 (5) | 0.0302 (5) | 0.0215 (5) | −0.0047 (4) | 0.0020 (4) | −0.0032 (4) |
N3 | 0.0367 (6) | 0.0263 (5) | 0.0181 (5) | −0.0020 (4) | 0.0005 (4) | −0.0010 (4) |
O1 | 0.0283 (5) | 0.0460 (5) | 0.0241 (4) | −0.0077 (4) | 0.0016 (3) | 0.0034 (4) |
O2 | 0.0481 (6) | 0.0267 (4) | 0.0258 (4) | −0.0057 (4) | 0.0022 (4) | 0.0016 (3) |
O3 | 0.0378 (5) | 0.0250 (4) | 0.0225 (4) | −0.0034 (4) | 0.0010 (3) | −0.0040 (3) |
C1—O1 | 1.2302 (14) | C12—C13 | 1.3707 (15) |
C1—N1 | 1.3924 (14) | C12—C17 | 1.5040 (16) |
C1—C2 | 1.4468 (17) | C13—C18 | 1.4464 (16) |
C2—C3 | 1.3586 (17) | C13—C14 | 1.5137 (15) |
C2—N3 | 1.4110 (14) | C14—C15 | 1.5171 (17) |
C3—N2 | 1.3840 (14) | C14—H14A | 0.99 |
C3—C4 | 1.4856 (17) | C14—H14B | 0.99 |
C4—H4A | 0.98 | C15—C16 | 1.5115 (19) |
C4—H4B | 0.98 | C15—H15A | 0.99 |
C4—H4C | 0.98 | C15—H15B | 0.99 |
C5—N2 | 1.4694 (15) | C16—C17 | 1.5235 (16) |
C5—H5A | 0.98 | C16—H16A | 0.99 |
C5—H5B | 0.98 | C16—H16B | 0.99 |
C5—H5C | 0.98 | C17—H17A | 0.99 |
C6—C7 | 1.3876 (16) | C17—H17B | 0.99 |
C6—C11 | 1.3882 (16) | C18—O2 | 1.2289 (14) |
C6—N1 | 1.4261 (14) | C18—O3 | 1.3562 (13) |
C7—C8 | 1.3862 (17) | C19—O3 | 1.4439 (14) |
C7—H7 | 0.95 | C19—C20 | 1.5061 (18) |
C8—C9 | 1.3828 (18) | C19—H19A | 0.99 |
C8—H8 | 0.95 | C19—H19B | 0.99 |
C9—C10 | 1.3830 (18) | C20—H20A | 0.98 |
C9—H9 | 0.95 | C20—H20B | 0.98 |
C10—C11 | 1.3856 (17) | C20—H20C | 0.98 |
C10—H10 | 0.95 | N1—N2 | 1.4118 (13) |
C11—H11 | 0.95 | N3—H3 | 0.896 (16) |
C12—N3 | 1.3679 (15) | ||
O1—C1—N1 | 124.35 (11) | C15—C14—H14A | 109 |
O1—C1—C2 | 131.25 (11) | C13—C14—H14B | 109 |
N1—C1—C2 | 104.39 (10) | C15—C14—H14B | 109 |
C3—C2—N3 | 126.34 (11) | H14A—C14—H14B | 107.8 |
C3—C2—C1 | 108.72 (10) | C16—C15—C14 | 110.09 (11) |
N3—C2—C1 | 124.54 (10) | C16—C15—H15A | 109.6 |
C2—C3—N2 | 109.92 (10) | C14—C15—H15A | 109.6 |
C2—C3—C4 | 129.23 (11) | C16—C15—H15B | 109.6 |
N2—C3—C4 | 120.85 (10) | C14—C15—H15B | 109.6 |
C3—C4—H4A | 109.5 | H15A—C15—H15B | 108.2 |
C3—C4—H4B | 109.5 | C15—C16—C17 | 109.66 (11) |
H4A—C4—H4B | 109.5 | C15—C16—H16A | 109.7 |
C3—C4—H4C | 109.5 | C17—C16—H16A | 109.7 |
H4A—C4—H4C | 109.5 | C15—C16—H16B | 109.7 |
H4B—C4—H4C | 109.5 | C17—C16—H16B | 109.7 |
N2—C5—H5A | 109.5 | H16A—C16—H16B | 108.2 |
N2—C5—H5B | 109.5 | C12—C17—C16 | 113.24 (10) |
H5A—C5—H5B | 109.5 | C12—C17—H17A | 108.9 |
N2—C5—H5C | 109.5 | C16—C17—H17A | 108.9 |
H5A—C5—H5C | 109.5 | C12—C17—H17B | 108.9 |
H5B—C5—H5C | 109.5 | C16—C17—H17B | 108.9 |
C7—C6—C11 | 120.54 (11) | H17A—C17—H17B | 107.7 |
C7—C6—N1 | 120.92 (10) | O2—C18—O3 | 120.68 (10) |
C11—C6—N1 | 118.55 (10) | O2—C18—C13 | 126.86 (10) |
C8—C7—C6 | 119.34 (11) | O3—C18—C13 | 112.46 (9) |
C8—C7—H7 | 120.3 | O3—C19—C20 | 107.49 (10) |
C6—C7—H7 | 120.3 | O3—C19—H19A | 110.2 |
C9—C8—C7 | 120.38 (11) | C20—C19—H19A | 110.2 |
C9—C8—H8 | 119.8 | O3—C19—H19B | 110.2 |
C7—C8—H8 | 119.8 | C20—C19—H19B | 110.2 |
C8—C9—C10 | 120.01 (11) | H19A—C19—H19B | 108.5 |
C8—C9—H9 | 120 | C19—C20—H20A | 109.5 |
C10—C9—H9 | 120 | C19—C20—H20B | 109.5 |
C9—C10—C11 | 120.22 (11) | H20A—C20—H20B | 109.5 |
C9—C10—H10 | 119.9 | C19—C20—H20C | 109.5 |
C11—C10—H10 | 119.9 | H20A—C20—H20C | 109.5 |
C10—C11—C6 | 119.51 (11) | H20B—C20—H20C | 109.5 |
C10—C11—H11 | 120.2 | C1—N1—N2 | 109.98 (9) |
C6—C11—H11 | 120.2 | C1—N1—C6 | 123.86 (10) |
N3—C12—C13 | 122.39 (10) | N2—N1—C6 | 120.08 (9) |
N3—C12—C17 | 115.68 (10) | C3—N2—N1 | 105.89 (9) |
C13—C12—C17 | 121.90 (10) | C3—N2—C5 | 120.39 (10) |
C12—C13—C18 | 120.43 (10) | N1—N2—C5 | 115.15 (9) |
C12—C13—C14 | 121.70 (10) | C12—N3—C2 | 124.33 (10) |
C18—C13—C14 | 117.85 (10) | C12—N3—H3 | 114.4 (10) |
C13—C14—C15 | 112.91 (9) | C2—N3—H3 | 120.3 (10) |
C13—C14—H14A | 109 | C18—O3—C19 | 115.81 (9) |
O1—C1—C2—C3 | 175.21 (12) | C12—C13—C18—O2 | −3.08 (19) |
N1—C1—C2—C3 | −3.53 (13) | C14—C13—C18—O2 | 178.25 (11) |
O1—C1—C2—N3 | 2.1 (2) | C12—C13—C18—O3 | 176.17 (10) |
N1—C1—C2—N3 | −176.63 (10) | C14—C13—C18—O3 | −2.50 (15) |
N3—C2—C3—N2 | 169.71 (11) | O1—C1—N1—N2 | −169.93 (11) |
C1—C2—C3—N2 | −3.24 (13) | C2—C1—N1—N2 | 8.92 (12) |
N3—C2—C3—C4 | −10.5 (2) | O1—C1—N1—C6 | −17.55 (18) |
C1—C2—C3—C4 | 176.55 (12) | C2—C1—N1—C6 | 161.30 (10) |
C11—C6—C7—C8 | 0.00 (19) | C7—C6—N1—C1 | −121.50 (13) |
N1—C6—C7—C8 | 179.98 (11) | C11—C6—N1—C1 | 58.49 (16) |
C6—C7—C8—C9 | 0.0 (2) | C7—C6—N1—N2 | 28.28 (16) |
C7—C8—C9—C10 | 0.1 (2) | C11—C6—N1—N2 | −151.74 (11) |
C8—C9—C10—C11 | −0.2 (2) | C2—C3—N2—N1 | 8.61 (13) |
C9—C10—C11—C6 | 0.18 (19) | C4—C3—N2—N1 | −171.21 (10) |
C7—C6—C11—C10 | −0.07 (19) | C2—C3—N2—C5 | 141.38 (11) |
N1—C6—C11—C10 | 179.95 (11) | C4—C3—N2—C5 | −38.44 (16) |
N3—C12—C13—C18 | 2.18 (17) | C1—N1—N2—C3 | −11.00 (12) |
C17—C12—C13—C18 | −175.80 (11) | C6—N1—N2—C3 | −164.59 (10) |
N3—C12—C13—C14 | −179.20 (10) | C1—N1—N2—C5 | −146.61 (10) |
C17—C12—C13—C14 | 2.82 (17) | C6—N1—N2—C5 | 59.80 (14) |
C12—C13—C14—C15 | 14.10 (16) | C13—C12—N3—C2 | 171.45 (11) |
C18—C13—C14—C15 | −167.24 (11) | C17—C12—N3—C2 | −10.46 (16) |
C13—C14—C15—C16 | −47.09 (14) | C3—C2—N3—C12 | 129.14 (13) |
C14—C15—C16—C17 | 63.96 (14) | C1—C2—N3—C12 | −58.97 (17) |
N3—C12—C17—C16 | −164.18 (11) | O2—C18—O3—C19 | 1.53 (16) |
C13—C12—C17—C16 | 13.92 (17) | C13—C18—O3—C19 | −177.77 (10) |
C15—C16—C17—C12 | −46.68 (15) | C20—C19—O3—C18 | −179.63 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.896 (16) | 1.934 (16) | 2.6618 (13) | 137 (1) |
C22H23N3O3 | F(000) = 800 |
Mr = 377.43 | Dx = 1.32 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9961 reflections |
a = 8.4851 (7) Å | θ = 3.2–28.2° |
b = 12.4253 (10) Å | µ = 0.09 mm−1 |
c = 18.0314 (18) Å | T = 173 K |
β = 92.282 (3)° | Plate, yellow |
V = 1899.5 (3) Å3 | 0.44 × 0.34 × 0.11 mm |
Z = 4 |
Bruker D8 Venture Photon diffractometer | 3838 reflections with I > 2σ(I) |
ω scans | Rint = 0.025 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.0°, θmin = 3.3° |
Tmin = 0.95, Tmax = 0.96 | h = −10→11 |
28673 measured reflections | k = −16→16 |
4570 independent reflections | l = −23→23 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0403P)2 + 0.6436P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.095 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.28 e Å−3 |
4570 reflections | Δρmin = −0.19 e Å−3 |
260 parameters |
C22H23N3O3 | V = 1899.5 (3) Å3 |
Mr = 377.43 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.4851 (7) Å | µ = 0.09 mm−1 |
b = 12.4253 (10) Å | T = 173 K |
c = 18.0314 (18) Å | 0.44 × 0.34 × 0.11 mm |
β = 92.282 (3)° |
Bruker D8 Venture Photon diffractometer | 4570 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3838 reflections with I > 2σ(I) |
Tmin = 0.95, Tmax = 0.96 | Rint = 0.025 |
28673 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.28 e Å−3 |
4570 reflections | Δρmin = −0.19 e Å−3 |
260 parameters |
Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.73101 (12) | 0.24095 (9) | 0.38575 (6) | 0.0235 (2) | |
C2 | 0.68561 (12) | 0.34800 (9) | 0.36110 (6) | 0.0228 (2) | |
C3 | 0.79944 (12) | 0.38855 (9) | 0.31873 (6) | 0.0220 (2) | |
C4 | 0.80437 (14) | 0.49224 (9) | 0.27788 (7) | 0.0277 (2) | |
H4A | 0.7825 | 0.4793 | 0.2248 | 0.042* | |
H4B | 0.9091 | 0.5247 | 0.2852 | 0.042* | |
H4C | 0.7247 | 0.5412 | 0.2967 | 0.042* | |
C5 | 0.98523 (15) | 0.29227 (10) | 0.24187 (6) | 0.0289 (3) | |
H5A | 0.9037 | 0.2555 | 0.2113 | 0.043* | |
H5B | 1.0782 | 0.2458 | 0.2478 | 0.043* | |
H5C | 1.0147 | 0.3595 | 0.2176 | 0.043* | |
C6 | 0.99274 (12) | 0.14792 (9) | 0.37750 (6) | 0.0210 (2) | |
C7 | 1.15038 (13) | 0.17856 (9) | 0.38681 (6) | 0.0238 (2) | |
H7 | 1.1819 | 0.2497 | 0.3751 | 0.029* | |
C8 | 1.26092 (13) | 0.10407 (10) | 0.41337 (6) | 0.0285 (2) | |
H8 | 1.3687 | 0.1242 | 0.4194 | 0.034* | |
C9 | 1.21484 (15) | 0.00056 (10) | 0.43107 (6) | 0.0305 (3) | |
H9 | 1.2902 | −0.0496 | 0.4505 | 0.037* | |
C10 | 1.05869 (15) | −0.02949 (9) | 0.42031 (6) | 0.0289 (3) | |
H10 | 1.0275 | −0.1008 | 0.4319 | 0.035* | |
C11 | 0.94718 (13) | 0.04313 (9) | 0.39279 (6) | 0.0250 (2) | |
H11 | 0.8406 | 0.0215 | 0.3844 | 0.03* | |
C12 | 0.42177 (12) | 0.41268 (8) | 0.32552 (6) | 0.0226 (2) | |
C13 | 0.43943 (12) | 0.36614 (9) | 0.25002 (6) | 0.0235 (2) | |
C14 | 0.46922 (13) | 0.25684 (10) | 0.23929 (7) | 0.0287 (2) | |
H14 | 0.48 | 0.21 | 0.2808 | 0.034* | |
C15 | 0.48312 (14) | 0.21660 (10) | 0.16805 (8) | 0.0343 (3) | |
H15 | 0.5039 | 0.1422 | 0.1612 | 0.041* | |
C16 | 0.46709 (14) | 0.28360 (11) | 0.10689 (7) | 0.0356 (3) | |
H16 | 0.4784 | 0.2556 | 0.0584 | 0.043* | |
C17 | 0.43452 (14) | 0.39154 (11) | 0.11684 (7) | 0.0323 (3) | |
H17 | 0.421 | 0.4376 | 0.075 | 0.039* | |
C18 | 0.42150 (13) | 0.43263 (10) | 0.18807 (7) | 0.0275 (2) | |
H18 | 0.4001 | 0.507 | 0.1946 | 0.033* | |
C19 | 0.28782 (13) | 0.46926 (9) | 0.33825 (6) | 0.0256 (2) | |
H19 | 0.2096 | 0.4728 | 0.2991 | 0.031* | |
C20 | 0.25582 (12) | 0.52413 (9) | 0.40659 (6) | 0.0249 (2) | |
C21 | 0.06614 (15) | 0.63645 (11) | 0.46383 (7) | 0.0336 (3) | |
H21A | 0.1338 | 0.701 | 0.4698 | 0.04* | |
H21B | 0.0747 | 0.5937 | 0.5102 | 0.04* | |
C22 | −0.10227 (15) | 0.66841 (12) | 0.44690 (7) | 0.0376 (3) | |
H22A | −0.1097 | 0.7066 | 0.3993 | 0.056* | |
H22B | −0.1384 | 0.7156 | 0.4863 | 0.056* | |
H22C | −0.1685 | 0.6038 | 0.444 | 0.056* | |
N1 | 0.87573 (10) | 0.22321 (7) | 0.35321 (5) | 0.0233 (2) | |
N2 | 0.92385 (10) | 0.31639 (7) | 0.31523 (5) | 0.02214 (19) | |
N3 | 0.54052 (11) | 0.39661 (8) | 0.37760 (6) | 0.0269 (2) | |
H3 | 0.5283 (17) | 0.4200 (12) | 0.4223 (9) | 0.036 (4)* | |
O1 | 0.66500 (9) | 0.17733 (7) | 0.42638 (5) | 0.0320 (2) | |
O2 | 0.34206 (10) | 0.52933 (8) | 0.46196 (5) | 0.0347 (2) | |
O3 | 0.11324 (10) | 0.57275 (7) | 0.40133 (5) | 0.0329 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0181 (5) | 0.0287 (6) | 0.0236 (5) | 0.0013 (4) | −0.0002 (4) | 0.0024 (4) |
C2 | 0.0199 (5) | 0.0268 (5) | 0.0215 (5) | 0.0039 (4) | −0.0006 (4) | 0.0012 (4) |
C3 | 0.0213 (5) | 0.0244 (5) | 0.0199 (5) | 0.0033 (4) | −0.0027 (4) | 0.0004 (4) |
C4 | 0.0283 (6) | 0.0258 (6) | 0.0292 (6) | 0.0036 (5) | 0.0016 (4) | 0.0055 (5) |
C5 | 0.0313 (6) | 0.0319 (6) | 0.0240 (6) | 0.0048 (5) | 0.0058 (4) | 0.0021 (5) |
C6 | 0.0208 (5) | 0.0234 (5) | 0.0188 (5) | 0.0044 (4) | 0.0009 (4) | −0.0001 (4) |
C7 | 0.0224 (5) | 0.0250 (5) | 0.0239 (5) | 0.0017 (4) | 0.0014 (4) | −0.0008 (4) |
C8 | 0.0213 (5) | 0.0389 (6) | 0.0252 (5) | 0.0063 (5) | 0.0000 (4) | −0.0011 (5) |
C9 | 0.0328 (6) | 0.0344 (6) | 0.0245 (5) | 0.0153 (5) | 0.0026 (5) | 0.0029 (5) |
C10 | 0.0396 (6) | 0.0223 (5) | 0.0251 (5) | 0.0055 (5) | 0.0057 (5) | 0.0025 (4) |
C11 | 0.0266 (5) | 0.0249 (5) | 0.0236 (5) | −0.0003 (4) | 0.0020 (4) | −0.0001 (4) |
C12 | 0.0192 (5) | 0.0197 (5) | 0.0290 (6) | −0.0008 (4) | 0.0012 (4) | 0.0028 (4) |
C13 | 0.0155 (5) | 0.0251 (5) | 0.0296 (6) | −0.0002 (4) | −0.0004 (4) | −0.0016 (4) |
C14 | 0.0235 (5) | 0.0247 (6) | 0.0378 (6) | 0.0002 (4) | 0.0012 (5) | 0.0006 (5) |
C15 | 0.0272 (6) | 0.0277 (6) | 0.0482 (8) | 0.0001 (5) | 0.0039 (5) | −0.0099 (5) |
C16 | 0.0265 (6) | 0.0462 (8) | 0.0341 (7) | −0.0036 (5) | 0.0026 (5) | −0.0121 (6) |
C17 | 0.0257 (6) | 0.0413 (7) | 0.0296 (6) | −0.0025 (5) | −0.0026 (5) | 0.0020 (5) |
C18 | 0.0220 (5) | 0.0264 (6) | 0.0337 (6) | 0.0008 (4) | −0.0027 (4) | −0.0002 (5) |
C19 | 0.0194 (5) | 0.0260 (5) | 0.0310 (6) | 0.0020 (4) | −0.0027 (4) | −0.0022 (4) |
C20 | 0.0190 (5) | 0.0249 (5) | 0.0307 (6) | 0.0019 (4) | 0.0000 (4) | 0.0025 (4) |
C21 | 0.0328 (6) | 0.0391 (7) | 0.0286 (6) | 0.0108 (5) | −0.0015 (5) | −0.0093 (5) |
C22 | 0.0329 (7) | 0.0473 (8) | 0.0328 (7) | 0.0130 (6) | 0.0033 (5) | −0.0082 (6) |
N1 | 0.0193 (4) | 0.0233 (5) | 0.0275 (5) | 0.0018 (4) | 0.0025 (3) | 0.0065 (4) |
N2 | 0.0212 (4) | 0.0226 (4) | 0.0228 (4) | 0.0023 (4) | 0.0028 (3) | 0.0048 (3) |
N3 | 0.0224 (5) | 0.0351 (5) | 0.0231 (5) | 0.0094 (4) | 0.0017 (4) | 0.0018 (4) |
O1 | 0.0240 (4) | 0.0344 (5) | 0.0380 (5) | 0.0014 (3) | 0.0071 (3) | 0.0121 (4) |
O2 | 0.0266 (4) | 0.0490 (5) | 0.0282 (4) | 0.0089 (4) | −0.0028 (3) | −0.0001 (4) |
O3 | 0.0251 (4) | 0.0415 (5) | 0.0317 (4) | 0.0127 (4) | −0.0039 (3) | −0.0110 (4) |
C1—O1 | 1.2280 (14) | C12—N3 | 1.3645 (14) |
C1—N1 | 1.3994 (14) | C12—C13 | 1.4920 (16) |
C1—C2 | 1.4497 (15) | C13—C18 | 1.3929 (16) |
C2—C3 | 1.3526 (15) | C13—C14 | 1.3963 (16) |
C2—N3 | 1.4135 (14) | C14—C15 | 1.3878 (18) |
C3—N2 | 1.3884 (14) | C14—H14 | 0.95 |
C3—C4 | 1.4855 (15) | C15—C16 | 1.384 (2) |
C4—H4A | 0.98 | C15—H15 | 0.95 |
C4—H4B | 0.98 | C16—C17 | 1.3825 (19) |
C4—H4C | 0.98 | C16—H16 | 0.95 |
C5—N2 | 1.4716 (14) | C17—C18 | 1.3905 (17) |
C5—H5A | 0.98 | C17—H17 | 0.95 |
C5—H5B | 0.98 | C18—H18 | 0.95 |
C5—H5C | 0.98 | C19—C20 | 1.4435 (16) |
C6—C11 | 1.3890 (15) | C19—H19 | 0.95 |
C6—C7 | 1.3945 (15) | C20—O2 | 1.2159 (14) |
C6—N1 | 1.4206 (13) | C20—O3 | 1.3522 (13) |
C7—C8 | 1.3892 (16) | C21—O3 | 1.4465 (14) |
C7—H7 | 0.95 | C21—C22 | 1.5027 (17) |
C8—C9 | 1.3852 (18) | C21—H21A | 0.99 |
C8—H8 | 0.95 | C21—H21B | 0.99 |
C9—C10 | 1.3828 (18) | C22—H22A | 0.98 |
C9—H9 | 0.95 | C22—H22B | 0.98 |
C10—C11 | 1.3850 (16) | C22—H22C | 0.98 |
C10—H10 | 0.95 | N1—N2 | 1.4136 (12) |
C11—H11 | 0.95 | N3—H3 | 0.867 (16) |
C12—C19 | 1.3637 (15) | ||
O1—C1—N1 | 125.27 (10) | C14—C13—C12 | 121.92 (10) |
O1—C1—C2 | 130.66 (10) | C15—C14—C13 | 120.08 (12) |
N1—C1—C2 | 104.05 (9) | C15—C14—H14 | 120 |
C3—C2—N3 | 127.39 (10) | C13—C14—H14 | 120 |
C3—C2—C1 | 109.14 (9) | C16—C15—C14 | 120.76 (12) |
N3—C2—C1 | 123.41 (10) | C16—C15—H15 | 119.6 |
C2—C3—N2 | 110.27 (10) | C14—C15—H15 | 119.6 |
C2—C3—C4 | 129.64 (10) | C17—C16—C15 | 119.60 (12) |
N2—C3—C4 | 120.08 (10) | C17—C16—H16 | 120.2 |
C3—C4—H4A | 109.5 | C15—C16—H16 | 120.2 |
C3—C4—H4B | 109.5 | C16—C17—C18 | 119.98 (12) |
H4A—C4—H4B | 109.5 | C16—C17—H17 | 120 |
C3—C4—H4C | 109.5 | C18—C17—H17 | 120 |
H4A—C4—H4C | 109.5 | C17—C18—C13 | 120.86 (11) |
H4B—C4—H4C | 109.5 | C17—C18—H18 | 119.6 |
N2—C5—H5A | 109.5 | C13—C18—H18 | 119.6 |
N2—C5—H5B | 109.5 | C12—C19—C20 | 125.00 (10) |
H5A—C5—H5B | 109.5 | C12—C19—H19 | 117.5 |
N2—C5—H5C | 109.5 | C20—C19—H19 | 117.5 |
H5A—C5—H5C | 109.5 | O2—C20—O3 | 122.78 (11) |
H5B—C5—H5C | 109.5 | O2—C20—C19 | 126.77 (10) |
C11—C6—C7 | 120.35 (10) | O3—C20—C19 | 110.44 (9) |
C11—C6—N1 | 118.81 (10) | O3—C21—C22 | 106.03 (10) |
C7—C6—N1 | 120.84 (10) | O3—C21—H21A | 110.5 |
C8—C7—C6 | 119.40 (11) | C22—C21—H21A | 110.5 |
C8—C7—H7 | 120.3 | O3—C21—H21B | 110.5 |
C6—C7—H7 | 120.3 | C22—C21—H21B | 110.5 |
C9—C8—C7 | 120.34 (11) | H21A—C21—H21B | 108.7 |
C9—C8—H8 | 119.8 | C21—C22—H22A | 109.5 |
C7—C8—H8 | 119.8 | C21—C22—H22B | 109.5 |
C10—C9—C8 | 119.74 (11) | H22A—C22—H22B | 109.5 |
C10—C9—H9 | 120.1 | C21—C22—H22C | 109.5 |
C8—C9—H9 | 120.1 | H22A—C22—H22C | 109.5 |
C9—C10—C11 | 120.76 (11) | H22B—C22—H22C | 109.5 |
C9—C10—H10 | 119.6 | C1—N1—N2 | 110.45 (8) |
C11—C10—H10 | 119.6 | C1—N1—C6 | 126.06 (9) |
C10—C11—C6 | 119.36 (11) | N2—N1—C6 | 118.48 (8) |
C10—C11—H11 | 120.3 | C3—N2—N1 | 105.79 (8) |
C6—C11—H11 | 120.3 | C3—N2—C5 | 117.99 (9) |
C19—C12—N3 | 123.86 (11) | N1—N2—C5 | 112.84 (9) |
C19—C12—C13 | 117.91 (10) | C12—N3—C2 | 122.90 (10) |
N3—C12—C13 | 118.23 (9) | C12—N3—H3 | 118.6 (10) |
C18—C13—C14 | 118.70 (11) | C2—N3—H3 | 118.4 (10) |
C18—C13—C12 | 119.35 (10) | C20—O3—C21 | 117.64 (9) |
O1—C1—C2—C3 | 177.76 (12) | N3—C12—C19—C20 | 3.14 (18) |
N1—C1—C2—C3 | −1.23 (12) | C13—C12—C19—C20 | −176.56 (10) |
O1—C1—C2—N3 | −4.83 (19) | C12—C19—C20—O2 | 0.8 (2) |
N1—C1—C2—N3 | 176.18 (10) | C12—C19—C20—O3 | 179.86 (11) |
N3—C2—C3—N2 | −179.52 (10) | O1—C1—N1—N2 | −174.85 (11) |
C1—C2—C3—N2 | −2.24 (13) | C2—C1—N1—N2 | 4.21 (11) |
N3—C2—C3—C4 | −0.6 (2) | O1—C1—N1—C6 | −20.54 (18) |
C1—C2—C3—C4 | 176.65 (11) | C2—C1—N1—C6 | 158.52 (10) |
C11—C6—C7—C8 | −1.65 (16) | C11—C6—N1—C1 | 47.88 (15) |
N1—C6—C7—C8 | 177.53 (10) | C7—C6—N1—C1 | −131.33 (12) |
C6—C7—C8—C9 | −0.57 (17) | C11—C6—N1—N2 | −159.65 (10) |
C7—C8—C9—C10 | 1.77 (17) | C7—C6—N1—N2 | 21.15 (15) |
C8—C9—C10—C11 | −0.75 (17) | C2—C3—N2—N1 | 4.75 (12) |
C9—C10—C11—C6 | −1.46 (17) | C4—C3—N2—N1 | −174.26 (9) |
C7—C6—C11—C10 | 2.66 (16) | C2—C3—N2—C5 | 132.13 (10) |
N1—C6—C11—C10 | −176.55 (10) | C4—C3—N2—C5 | −46.89 (14) |
C19—C12—C13—C18 | 52.83 (14) | C1—N1—N2—C3 | −5.60 (11) |
N3—C12—C13—C18 | −126.89 (11) | C6—N1—N2—C3 | −162.10 (9) |
C19—C12—C13—C14 | −125.36 (12) | C1—N1—N2—C5 | −136.01 (9) |
N3—C12—C13—C14 | 54.92 (15) | C6—N1—N2—C5 | 67.49 (12) |
C18—C13—C14—C15 | 1.09 (16) | C19—C12—N3—C2 | −172.86 (11) |
C12—C13—C14—C15 | 179.29 (10) | C13—C12—N3—C2 | 6.85 (16) |
C13—C14—C15—C16 | −0.29 (18) | C3—C2—N3—C12 | 68.10 (17) |
C14—C15—C16—C17 | −0.97 (18) | C1—C2—N3—C12 | −108.82 (13) |
C15—C16—C17—C18 | 1.41 (18) | O2—C20—O3—C21 | 2.31 (17) |
C16—C17—C18—C13 | −0.60 (17) | C19—C20—O3—C21 | −176.77 (10) |
C14—C13—C18—C17 | −0.65 (16) | C22—C21—O3—C20 | −173.01 (11) |
C12—C13—C18—C17 | −178.90 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.867 (16) | 2.224 (15) | 2.8413 (13) | 128 (1) |
N3—H3···O2i | 0.867 (16) | 2.404 (16) | 3.1590 (14) | 146 (1) |
C8—H8···O1ii | 0.95 | 2.6 | 3.5462 (15) | 176 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z. |
C14H14N4O2 | F(000) = 568 |
Mr = 270.29 | Dx = 1.332 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9915 reflections |
a = 6.9996 (8) Å | θ = 3.1–28.3° |
b = 12.3350 (16) Å | µ = 0.09 mm−1 |
c = 15.8345 (19) Å | T = 173 K |
β = 99.666 (4)° | Needle, colourless |
V = 1347.7 (3) Å3 | 0.67 × 0.16 × 0.11 mm |
Z = 4 |
Bruker D8 Venture Photon diffractometer | 2737 reflections with I > 2σ(I) |
ω scans | Rint = 0.023 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.0°, θmin = 3.4° |
Tmin = 0.98, Tmax = 0.99 | h = −9→8 |
19472 measured reflections | k = −16→16 |
3252 independent reflections | l = −20→20 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0482P)2 + 0.3708P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.097 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.27 e Å−3 |
3252 reflections | Δρmin = −0.18 e Å−3 |
187 parameters |
C14H14N4O2 | V = 1347.7 (3) Å3 |
Mr = 270.29 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.9996 (8) Å | µ = 0.09 mm−1 |
b = 12.3350 (16) Å | T = 173 K |
c = 15.8345 (19) Å | 0.67 × 0.16 × 0.11 mm |
β = 99.666 (4)° |
Bruker D8 Venture Photon diffractometer | 3252 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2737 reflections with I > 2σ(I) |
Tmin = 0.98, Tmax = 0.99 | Rint = 0.023 |
19472 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.27 e Å−3 |
3252 reflections | Δρmin = −0.18 e Å−3 |
187 parameters |
Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.34738 (14) | 0.45507 (8) | 0.10778 (6) | 0.0226 (2) | |
C2 | 0.23701 (14) | 0.55169 (8) | 0.08681 (7) | 0.0231 (2) | |
C3 | 0.05925 (15) | 0.53893 (8) | 0.11050 (7) | 0.0246 (2) | |
C4 | −0.10439 (16) | 0.61652 (10) | 0.10627 (8) | 0.0327 (3) | |
H4A | −0.1001 | 0.6511 | 0.1623 | 0.049* | |
H4B | −0.2273 | 0.5776 | 0.0907 | 0.049* | |
H4C | −0.0937 | 0.6721 | 0.0631 | 0.049* | |
C5 | −0.05781 (17) | 0.41025 (11) | 0.21283 (8) | 0.0349 (3) | |
H5A | 0.012 | 0.4399 | 0.2667 | 0.052* | |
H5B | −0.068 | 0.3313 | 0.2178 | 0.052* | |
H5C | −0.188 | 0.4419 | 0.2007 | 0.052* | |
C6 | 0.25170 (15) | 0.27381 (9) | 0.15402 (7) | 0.0251 (2) | |
C7 | 0.11104 (18) | 0.20547 (10) | 0.11078 (8) | 0.0346 (3) | |
H7 | −0.0041 | 0.2344 | 0.0783 | 0.041* | |
C8 | 0.1407 (2) | 0.09414 (11) | 0.11558 (9) | 0.0438 (3) | |
H8 | 0.044 | 0.0465 | 0.0873 | 0.053* | |
C9 | 0.3095 (2) | 0.05252 (10) | 0.16110 (9) | 0.0436 (3) | |
H9 | 0.3303 | −0.0236 | 0.1631 | 0.052* | |
C10 | 0.4488 (2) | 0.12139 (11) | 0.20388 (9) | 0.0408 (3) | |
H10 | 0.5653 | 0.0923 | 0.2351 | 0.049* | |
C11 | 0.42005 (17) | 0.23284 (10) | 0.20169 (7) | 0.0311 (2) | |
H11 | 0.5142 | 0.2801 | 0.2324 | 0.037* | |
C12 | 0.32054 (15) | 0.74122 (9) | 0.06778 (7) | 0.0258 (2) | |
C13 | 0.41768 (18) | 0.81538 (9) | 0.00944 (8) | 0.0327 (3) | |
H13A | 0.4643 | 0.7711 | −0.0351 | 0.039* | |
H13B | 0.3212 | 0.8677 | −0.0197 | 0.039* | |
C14 | 0.58016 (17) | 0.87440 (10) | 0.05817 (8) | 0.0339 (3) | |
N1 | 0.22982 (12) | 0.38856 (7) | 0.14719 (6) | 0.0247 (2) | |
N2 | 0.04759 (12) | 0.43659 (7) | 0.14307 (6) | 0.0255 (2) | |
N3 | 0.30922 (13) | 0.63698 (7) | 0.04169 (6) | 0.0252 (2) | |
H3 | 0.375 (2) | 0.6174 (12) | −0.0003 (9) | 0.036 (4)* | |
N4 | 0.70659 (18) | 0.92148 (12) | 0.09499 (9) | 0.0551 (3) | |
O1 | 0.51052 (10) | 0.42821 (6) | 0.09377 (5) | 0.02694 (18) | |
O2 | 0.25709 (13) | 0.77685 (7) | 0.12907 (5) | 0.0345 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0215 (5) | 0.0229 (5) | 0.0232 (5) | −0.0034 (4) | 0.0033 (4) | −0.0020 (4) |
C2 | 0.0218 (5) | 0.0207 (5) | 0.0265 (5) | −0.0024 (4) | 0.0037 (4) | −0.0016 (4) |
C3 | 0.0224 (5) | 0.0242 (5) | 0.0267 (5) | −0.0022 (4) | 0.0024 (4) | −0.0028 (4) |
C4 | 0.0240 (5) | 0.0304 (6) | 0.0441 (7) | 0.0030 (4) | 0.0075 (5) | −0.0004 (5) |
C5 | 0.0271 (5) | 0.0451 (7) | 0.0349 (6) | 0.0021 (5) | 0.0127 (5) | 0.0062 (5) |
C6 | 0.0273 (5) | 0.0230 (5) | 0.0262 (5) | −0.0017 (4) | 0.0080 (4) | 0.0028 (4) |
C7 | 0.0336 (6) | 0.0318 (6) | 0.0374 (6) | −0.0078 (5) | 0.0034 (5) | 0.0018 (5) |
C8 | 0.0554 (8) | 0.0291 (6) | 0.0493 (8) | −0.0148 (6) | 0.0162 (6) | −0.0043 (5) |
C9 | 0.0616 (9) | 0.0229 (5) | 0.0538 (8) | 0.0021 (6) | 0.0315 (7) | 0.0066 (5) |
C10 | 0.0448 (7) | 0.0367 (7) | 0.0438 (7) | 0.0114 (5) | 0.0159 (6) | 0.0160 (6) |
C11 | 0.0307 (5) | 0.0324 (6) | 0.0299 (6) | 0.0007 (5) | 0.0048 (4) | 0.0054 (5) |
C12 | 0.0241 (5) | 0.0230 (5) | 0.0288 (5) | −0.0017 (4) | 0.0000 (4) | 0.0009 (4) |
C13 | 0.0382 (6) | 0.0260 (5) | 0.0332 (6) | −0.0068 (5) | 0.0039 (5) | 0.0036 (5) |
C14 | 0.0301 (6) | 0.0305 (6) | 0.0424 (7) | −0.0026 (5) | 0.0104 (5) | 0.0031 (5) |
N1 | 0.0193 (4) | 0.0234 (4) | 0.0321 (5) | −0.0004 (3) | 0.0065 (3) | 0.0018 (4) |
N2 | 0.0189 (4) | 0.0263 (4) | 0.0323 (5) | −0.0001 (3) | 0.0069 (3) | 0.0017 (4) |
N3 | 0.0258 (4) | 0.0214 (4) | 0.0295 (5) | −0.0026 (3) | 0.0078 (4) | 0.0001 (4) |
N4 | 0.0384 (6) | 0.0614 (8) | 0.0645 (8) | −0.0176 (6) | 0.0056 (6) | −0.0012 (7) |
O1 | 0.0205 (3) | 0.0281 (4) | 0.0333 (4) | 0.0005 (3) | 0.0078 (3) | 0.0015 (3) |
O2 | 0.0416 (5) | 0.0268 (4) | 0.0365 (4) | −0.0031 (3) | 0.0109 (4) | −0.0052 (3) |
C1—O1 | 1.2442 (12) | C7—H7 | 0.95 |
C1—N1 | 1.3828 (13) | C8—C9 | 1.376 (2) |
C1—C2 | 1.4288 (15) | C8—H8 | 0.95 |
C2—C3 | 1.3676 (14) | C9—C10 | 1.382 (2) |
C2—N3 | 1.4120 (13) | C9—H9 | 0.95 |
C3—N2 | 1.3713 (14) | C10—C11 | 1.3889 (18) |
C3—C4 | 1.4855 (15) | C10—H10 | 0.95 |
C4—H4A | 0.98 | C11—H11 | 0.95 |
C4—H4B | 0.98 | C12—O2 | 1.2153 (14) |
C4—H4C | 0.98 | C12—N3 | 1.3489 (14) |
C5—N2 | 1.4641 (14) | C12—C13 | 1.5373 (15) |
C5—H5A | 0.98 | C13—C14 | 1.4575 (17) |
C5—H5B | 0.98 | C13—H13A | 0.99 |
C5—H5C | 0.98 | C13—H13B | 0.99 |
C6—C11 | 1.3839 (16) | C14—N4 | 1.1345 (17) |
C6—C7 | 1.3865 (16) | N1—N2 | 1.3980 (12) |
C6—N1 | 1.4258 (14) | N3—H3 | 0.903 (15) |
C7—C8 | 1.3890 (18) | ||
O1—C1—N1 | 123.78 (9) | C7—C8—H8 | 119.8 |
O1—C1—C2 | 131.09 (10) | C8—C9—C10 | 120.05 (12) |
N1—C1—C2 | 105.09 (8) | C8—C9—H9 | 120 |
C3—C2—N3 | 130.09 (10) | C10—C9—H9 | 120 |
C3—C2—C1 | 108.75 (9) | C9—C10—C11 | 120.57 (12) |
N3—C2—C1 | 120.90 (9) | C9—C10—H10 | 119.7 |
C2—C3—N2 | 108.87 (9) | C11—C10—H10 | 119.7 |
C2—C3—C4 | 130.06 (10) | C6—C11—C10 | 118.80 (12) |
N2—C3—C4 | 121.06 (9) | C6—C11—H11 | 120.6 |
C3—C4—H4A | 109.5 | C10—C11—H11 | 120.6 |
C3—C4—H4B | 109.5 | O2—C12—N3 | 125.37 (10) |
H4A—C4—H4B | 109.5 | O2—C12—C13 | 121.50 (10) |
C3—C4—H4C | 109.5 | N3—C12—C13 | 113.10 (10) |
H4A—C4—H4C | 109.5 | C14—C13—C12 | 111.32 (10) |
H4B—C4—H4C | 109.5 | C14—C13—H13A | 109.4 |
N2—C5—H5A | 109.5 | C12—C13—H13A | 109.4 |
N2—C5—H5B | 109.5 | C14—C13—H13B | 109.4 |
H5A—C5—H5B | 109.5 | C12—C13—H13B | 109.4 |
N2—C5—H5C | 109.5 | H13A—C13—H13B | 108 |
H5A—C5—H5C | 109.5 | N4—C14—C13 | 178.86 (14) |
H5B—C5—H5C | 109.5 | C1—N1—N2 | 109.57 (8) |
C11—C6—C7 | 121.09 (11) | C1—N1—C6 | 123.96 (9) |
C11—C6—N1 | 118.34 (10) | N2—N1—C6 | 120.65 (8) |
C7—C6—N1 | 120.52 (10) | C3—N2—N1 | 107.23 (8) |
C6—C7—C8 | 119.13 (12) | C3—N2—C5 | 123.88 (9) |
C6—C7—H7 | 120.4 | N1—N2—C5 | 116.24 (9) |
C8—C7—H7 | 120.4 | C12—N3—C2 | 124.25 (9) |
C9—C8—C7 | 120.33 (13) | C12—N3—H3 | 118.1 (9) |
C9—C8—H8 | 119.8 | C2—N3—H3 | 116.3 (9) |
O1—C1—C2—C3 | 175.50 (11) | C2—C1—N1—N2 | 5.83 (11) |
N1—C1—C2—C3 | −2.28 (11) | O1—C1—N1—C6 | −19.06 (16) |
O1—C1—C2—N3 | 0.73 (17) | C2—C1—N1—C6 | 158.93 (9) |
N1—C1—C2—N3 | −177.05 (9) | C11—C6—N1—C1 | 64.08 (14) |
N3—C2—C3—N2 | 171.96 (10) | C7—C6—N1—C1 | −113.18 (12) |
C1—C2—C3—N2 | −2.17 (12) | C11—C6—N1—N2 | −145.63 (10) |
N3—C2—C3—C4 | −8.91 (19) | C7—C6—N1—N2 | 37.12 (15) |
C1—C2—C3—C4 | 176.96 (11) | C2—C3—N2—N1 | 5.73 (11) |
C11—C6—C7—C8 | −0.10 (18) | C4—C3—N2—N1 | −173.49 (10) |
N1—C6—C7—C8 | 177.09 (11) | C2—C3—N2—C5 | 145.71 (10) |
C6—C7—C8—C9 | −1.4 (2) | C4—C3—N2—C5 | −33.51 (15) |
C7—C8—C9—C10 | 1.4 (2) | C1—N1—N2—C3 | −7.30 (11) |
C8—C9—C10—C11 | 0.21 (19) | C6—N1—N2—C3 | −161.43 (9) |
C7—C6—C11—C10 | 1.66 (17) | C1—N1—N2—C5 | −150.77 (10) |
N1—C6—C11—C10 | −175.58 (10) | C6—N1—N2—C5 | 55.10 (13) |
C9—C10—C11—C6 | −1.72 (18) | O2—C12—N3—C2 | −6.09 (17) |
O2—C12—C13—C14 | 56.70 (15) | C13—C12—N3—C2 | 176.09 (9) |
N3—C12—C13—C14 | −125.39 (11) | C3—C2—N3—C12 | 58.82 (16) |
O1—C1—N1—N2 | −172.16 (9) | C1—C2—N3—C12 | −127.66 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1i | 0.903 (15) | 1.884 (15) | 2.7835 (12) | 174 (1) |
C9—H9···O2ii | 0.95 | 2.55 | 3.4485 (16) | 157 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y−1, z. |
C20H19N3O3 | F(000) = 1472 |
Mr = 349.38 | Dx = 1.298 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 8137 reflections |
a = 32.7563 (10) Å | θ = 2.6–28.0° |
b = 6.9258 (2) Å | µ = 0.09 mm−1 |
c = 16.4002 (5) Å | T = 173 K |
β = 106.032 (1)° | Plate, yellow |
V = 3575.90 (19) Å3 | 0.68 × 0.24 × 0.09 mm |
Z = 8 |
Bruker D8 Venture Photon diffractometer | 3539 reflections with I > 2σ(I) |
ω scans | Rint = 0.040 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.0°, θmin = 2.6° |
Tmin = 0.95, Tmax = 0.99 | h = −41→43 |
31732 measured reflections | k = −9→8 |
4312 independent reflections | l = −21→20 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + (0.0539P)2 + 2.065P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.110 | (Δ/σ)max = 0.002 |
S = 1.03 | Δρmax = 0.24 e Å−3 |
4312 reflections | Δρmin = −0.30 e Å−3 |
238 parameters |
C20H19N3O3 | V = 3575.90 (19) Å3 |
Mr = 349.38 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 32.7563 (10) Å | µ = 0.09 mm−1 |
b = 6.9258 (2) Å | T = 173 K |
c = 16.4002 (5) Å | 0.68 × 0.24 × 0.09 mm |
β = 106.032 (1)° |
Bruker D8 Venture Photon diffractometer | 4312 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3539 reflections with I > 2σ(I) |
Tmin = 0.95, Tmax = 0.99 | Rint = 0.040 |
31732 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.24 e Å−3 |
4312 reflections | Δρmin = −0.30 e Å−3 |
238 parameters |
Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.31423 (4) | 0.32838 (17) | 0.65668 (7) | 0.0249 (2) | |
C2 | 0.27746 (4) | 0.20497 (17) | 0.64224 (7) | 0.0241 (2) | |
C3 | 0.28930 (4) | 0.03859 (17) | 0.68905 (7) | 0.0249 (2) | |
C4 | 0.26341 (4) | −0.13591 (19) | 0.69093 (8) | 0.0347 (3) | |
H4A | 0.2742 | −0.2437 | 0.6642 | 0.052* | |
H4B | 0.2338 | −0.1104 | 0.6599 | 0.052* | |
H4C | 0.2652 | −0.169 | 0.7499 | 0.052* | |
C5 | 0.35913 (4) | −0.11026 (18) | 0.76603 (8) | 0.0323 (3) | |
H5A | 0.3425 | −0.2272 | 0.7677 | 0.048* | |
H5B | 0.3771 | −0.0814 | 0.8232 | 0.048* | |
H5C | 0.3771 | −0.1307 | 0.7279 | 0.048* | |
C6 | 0.38177 (4) | 0.31383 (17) | 0.77103 (7) | 0.0256 (2) | |
C7 | 0.38420 (4) | 0.31516 (19) | 0.85699 (8) | 0.0315 (3) | |
H7 | 0.3631 | 0.2521 | 0.8771 | 0.038* | |
C8 | 0.41769 (5) | 0.4094 (2) | 0.91302 (8) | 0.0371 (3) | |
H8 | 0.4198 | 0.4095 | 0.972 | 0.045* | |
C9 | 0.44812 (4) | 0.5036 (2) | 0.88369 (9) | 0.0390 (3) | |
H9 | 0.471 | 0.5679 | 0.9224 | 0.047* | |
C10 | 0.44513 (4) | 0.5039 (2) | 0.79796 (9) | 0.0368 (3) | |
H10 | 0.4658 | 0.5701 | 0.7779 | 0.044* | |
C11 | 0.41205 (4) | 0.40798 (18) | 0.74104 (8) | 0.0307 (3) | |
H11 | 0.4102 | 0.4069 | 0.6822 | 0.037* | |
C12 | 0.22522 (4) | 0.39995 (18) | 0.55655 (7) | 0.0265 (2) | |
H12 | 0.2467 | 0.4883 | 0.5522 | 0.032* | |
C13 | 0.18049 (4) | 0.44398 (18) | 0.51512 (7) | 0.0256 (2) | |
C14 | 0.16980 (4) | 0.62384 (18) | 0.47654 (7) | 0.0277 (3) | |
H14 | 0.1915 | 0.7145 | 0.4764 | 0.033* | |
C15 | 0.12782 (4) | 0.67091 (18) | 0.43851 (7) | 0.0278 (3) | |
H15 | 0.1208 | 0.7938 | 0.4127 | 0.033* | |
C16 | 0.09584 (4) | 0.53855 (18) | 0.43809 (7) | 0.0264 (2) | |
C17 | 0.10635 (4) | 0.35766 (18) | 0.47584 (8) | 0.0293 (3) | |
H17 | 0.0846 | 0.2664 | 0.4753 | 0.035* | |
C18 | 0.14830 (4) | 0.31137 (18) | 0.51399 (7) | 0.0294 (3) | |
H18 | 0.1553 | 0.1883 | 0.5396 | 0.035* | |
C19 | 0.05106 (4) | 0.59546 (19) | 0.39791 (8) | 0.0309 (3) | |
C20 | −0.02046 (5) | 0.4949 (3) | 0.35914 (14) | 0.0618 (5) | |
H20A | −0.0302 | 0.581 | 0.3974 | 0.093* | |
H20B | −0.037 | 0.3753 | 0.3512 | 0.093* | |
H20C | −0.0243 | 0.5587 | 0.3042 | 0.093* | |
N1 | 0.34734 (3) | 0.22117 (14) | 0.71114 (6) | 0.0262 (2) | |
N2 | 0.33035 (3) | 0.05151 (14) | 0.73522 (6) | 0.0269 (2) | |
N3 | 0.23550 (3) | 0.24258 (15) | 0.59866 (6) | 0.0261 (2) | |
O1 | 0.31896 (3) | 0.49344 (13) | 0.63305 (6) | 0.0333 (2) | |
O2 | 0.03997 (3) | 0.75497 (15) | 0.37135 (7) | 0.0445 (3) | |
O3 | 0.02396 (3) | 0.45057 (14) | 0.39547 (8) | 0.0489 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0240 (6) | 0.0246 (6) | 0.0258 (5) | 0.0030 (5) | 0.0063 (4) | 0.0011 (4) |
C2 | 0.0237 (5) | 0.0249 (6) | 0.0247 (5) | 0.0010 (5) | 0.0084 (4) | −0.0007 (4) |
C3 | 0.0268 (6) | 0.0254 (6) | 0.0241 (5) | −0.0001 (5) | 0.0093 (4) | −0.0010 (4) |
C4 | 0.0355 (7) | 0.0312 (7) | 0.0373 (6) | −0.0060 (6) | 0.0100 (5) | 0.0037 (5) |
C5 | 0.0374 (7) | 0.0244 (6) | 0.0314 (6) | 0.0058 (5) | 0.0033 (5) | 0.0048 (5) |
C6 | 0.0231 (6) | 0.0208 (6) | 0.0312 (6) | 0.0034 (4) | 0.0044 (4) | 0.0020 (4) |
C7 | 0.0334 (6) | 0.0282 (6) | 0.0336 (6) | −0.0021 (5) | 0.0102 (5) | 0.0001 (5) |
C8 | 0.0457 (8) | 0.0318 (7) | 0.0307 (6) | −0.0027 (6) | 0.0051 (5) | −0.0016 (5) |
C9 | 0.0376 (7) | 0.0289 (7) | 0.0427 (7) | −0.0064 (6) | −0.0019 (6) | −0.0001 (5) |
C10 | 0.0303 (6) | 0.0319 (7) | 0.0465 (7) | −0.0051 (6) | 0.0080 (5) | 0.0058 (6) |
C11 | 0.0296 (6) | 0.0291 (6) | 0.0331 (6) | 0.0010 (5) | 0.0080 (5) | 0.0044 (5) |
C12 | 0.0244 (6) | 0.0292 (6) | 0.0266 (5) | 0.0008 (5) | 0.0081 (4) | −0.0007 (4) |
C13 | 0.0245 (6) | 0.0297 (6) | 0.0232 (5) | 0.0029 (5) | 0.0073 (4) | −0.0007 (4) |
C14 | 0.0262 (6) | 0.0294 (6) | 0.0287 (5) | −0.0010 (5) | 0.0095 (4) | 0.0021 (5) |
C15 | 0.0288 (6) | 0.0269 (6) | 0.0277 (5) | 0.0026 (5) | 0.0080 (5) | 0.0036 (4) |
C16 | 0.0255 (6) | 0.0285 (6) | 0.0246 (5) | 0.0025 (5) | 0.0062 (4) | 0.0003 (4) |
C17 | 0.0264 (6) | 0.0269 (6) | 0.0339 (6) | −0.0015 (5) | 0.0075 (5) | 0.0022 (5) |
C18 | 0.0285 (6) | 0.0272 (6) | 0.0319 (6) | 0.0024 (5) | 0.0076 (5) | 0.0042 (5) |
C19 | 0.0270 (6) | 0.0308 (7) | 0.0323 (6) | 0.0001 (5) | 0.0040 (5) | 0.0010 (5) |
C20 | 0.0250 (7) | 0.0426 (9) | 0.1037 (14) | −0.0035 (7) | −0.0057 (8) | 0.0077 (9) |
N1 | 0.0250 (5) | 0.0212 (5) | 0.0305 (5) | −0.0009 (4) | 0.0046 (4) | 0.0045 (4) |
N2 | 0.0279 (5) | 0.0199 (5) | 0.0312 (5) | −0.0002 (4) | 0.0055 (4) | 0.0041 (4) |
N3 | 0.0231 (5) | 0.0304 (5) | 0.0248 (4) | 0.0028 (4) | 0.0066 (4) | −0.0009 (4) |
O1 | 0.0306 (5) | 0.0244 (5) | 0.0417 (5) | −0.0001 (4) | 0.0044 (4) | 0.0087 (4) |
O2 | 0.0296 (5) | 0.0381 (6) | 0.0599 (6) | 0.0034 (4) | 0.0024 (4) | 0.0176 (5) |
O3 | 0.0251 (5) | 0.0311 (6) | 0.0800 (8) | −0.0017 (4) | −0.0030 (5) | 0.0054 (5) |
C1—O1 | 1.2305 (14) | C10—H10 | 0.95 |
C1—N1 | 1.4109 (14) | C11—H11 | 0.95 |
C1—C2 | 1.4421 (16) | C12—N3 | 1.2844 (16) |
C2—C3 | 1.3795 (16) | C12—C13 | 1.4670 (16) |
C2—N3 | 1.3875 (14) | C12—H12 | 0.95 |
C3—N2 | 1.3518 (15) | C13—C18 | 1.3946 (17) |
C3—C4 | 1.4815 (17) | C13—C14 | 1.3972 (17) |
C4—H4A | 0.98 | C14—C15 | 1.3831 (16) |
C4—H4B | 0.98 | C14—H14 | 0.95 |
C4—H4C | 0.98 | C15—C16 | 1.3904 (17) |
C5—N2 | 1.4614 (15) | C15—H15 | 0.95 |
C5—H5A | 0.98 | C16—C17 | 1.3977 (17) |
C5—H5B | 0.98 | C16—C19 | 1.4857 (16) |
C5—H5C | 0.98 | C17—C18 | 1.3810 (17) |
C6—C11 | 1.3859 (17) | C17—H17 | 0.95 |
C6—C7 | 1.3898 (17) | C18—H18 | 0.95 |
C6—N1 | 1.4271 (15) | C19—O2 | 1.2062 (16) |
C7—C8 | 1.3846 (19) | C19—O3 | 1.3330 (16) |
C7—H7 | 0.95 | C20—O3 | 1.4449 (17) |
C8—C9 | 1.384 (2) | C20—H20A | 0.98 |
C8—H8 | 0.95 | C20—H20B | 0.98 |
C9—C10 | 1.382 (2) | C20—H20C | 0.98 |
C9—H9 | 0.95 | N1—N2 | 1.4028 (14) |
C10—C11 | 1.3884 (18) | ||
O1—C1—N1 | 123.13 (11) | N3—C12—C13 | 120.35 (11) |
O1—C1—C2 | 132.14 (11) | N3—C12—H12 | 119.8 |
N1—C1—C2 | 104.67 (10) | C13—C12—H12 | 119.8 |
C3—C2—N3 | 121.99 (11) | C18—C13—C14 | 119.15 (11) |
C3—C2—C1 | 108.06 (10) | C18—C13—C12 | 121.61 (11) |
N3—C2—C1 | 129.56 (11) | C14—C13—C12 | 119.23 (11) |
N2—C3—C2 | 109.86 (10) | C15—C14—C13 | 120.52 (11) |
N2—C3—C4 | 121.93 (11) | C15—C14—H14 | 119.7 |
C2—C3—C4 | 128.20 (11) | C13—C14—H14 | 119.7 |
C3—C4—H4A | 109.5 | C14—C15—C16 | 120.04 (11) |
C3—C4—H4B | 109.5 | C14—C15—H15 | 120 |
H4A—C4—H4B | 109.5 | C16—C15—H15 | 120 |
C3—C4—H4C | 109.5 | C15—C16—C17 | 119.72 (11) |
H4A—C4—H4C | 109.5 | C15—C16—C19 | 118.51 (11) |
H4B—C4—H4C | 109.5 | C17—C16—C19 | 121.77 (11) |
N2—C5—H5A | 109.5 | C18—C17—C16 | 120.08 (11) |
N2—C5—H5B | 109.5 | C18—C17—H17 | 120 |
H5A—C5—H5B | 109.5 | C16—C17—H17 | 120 |
N2—C5—H5C | 109.5 | C17—C18—C13 | 120.47 (12) |
H5A—C5—H5C | 109.5 | C17—C18—H18 | 119.8 |
H5B—C5—H5C | 109.5 | C13—C18—H18 | 119.8 |
C11—C6—C7 | 120.72 (11) | O2—C19—O3 | 123.15 (11) |
C11—C6—N1 | 118.31 (10) | O2—C19—C16 | 124.43 (12) |
C7—C6—N1 | 120.94 (11) | O3—C19—C16 | 112.42 (11) |
C8—C7—C6 | 119.29 (12) | O3—C20—H20A | 109.5 |
C8—C7—H7 | 120.4 | O3—C20—H20B | 109.5 |
C6—C7—H7 | 120.4 | H20A—C20—H20B | 109.5 |
C9—C8—C7 | 120.40 (12) | O3—C20—H20C | 109.5 |
C9—C8—H8 | 119.8 | H20A—C20—H20C | 109.5 |
C7—C8—H8 | 119.8 | H20B—C20—H20C | 109.5 |
C10—C9—C8 | 119.92 (12) | N2—N1—C1 | 108.88 (9) |
C10—C9—H9 | 120 | N2—N1—C6 | 118.85 (9) |
C8—C9—H9 | 120 | C1—N1—C6 | 121.49 (10) |
C9—C10—C11 | 120.42 (12) | C3—N2—N1 | 107.96 (9) |
C9—C10—H10 | 119.8 | C3—N2—C5 | 126.14 (10) |
C11—C10—H10 | 119.8 | N1—N2—C5 | 118.12 (9) |
C6—C11—C10 | 119.24 (12) | C12—N3—C2 | 120.76 (10) |
C6—C11—H11 | 120.4 | C19—O3—C20 | 116.02 (11) |
C10—C11—H11 | 120.4 | ||
O1—C1—C2—C3 | −175.46 (12) | C12—C13—C18—C17 | 178.86 (11) |
N1—C1—C2—C3 | 1.93 (12) | C15—C16—C19—O2 | −6.30 (19) |
O1—C1—C2—N3 | −2.7 (2) | C17—C16—C19—O2 | 173.01 (13) |
N1—C1—C2—N3 | 174.70 (11) | C15—C16—C19—O3 | 174.72 (11) |
N3—C2—C3—N2 | −170.52 (10) | C17—C16—C19—O3 | −5.97 (17) |
C1—C2—C3—N2 | 2.91 (13) | O1—C1—N1—N2 | 171.78 (11) |
N3—C2—C3—C4 | 10.72 (18) | C2—C1—N1—N2 | −5.91 (12) |
C1—C2—C3—C4 | −175.85 (11) | O1—C1—N1—C6 | 27.94 (16) |
C11—C6—C7—C8 | −0.97 (19) | C2—C1—N1—C6 | −149.75 (10) |
N1—C6—C7—C8 | −178.87 (12) | C11—C6—N1—N2 | 146.60 (11) |
C6—C7—C8—C9 | 0.9 (2) | C7—C6—N1—N2 | −35.45 (16) |
C7—C8—C9—C10 | 0.1 (2) | C11—C6—N1—C1 | −72.99 (14) |
C8—C9—C10—C11 | −0.9 (2) | C7—C6—N1—C1 | 104.96 (13) |
C7—C6—C11—C10 | 0.17 (19) | C2—C3—N2—N1 | −6.64 (12) |
N1—C6—C11—C10 | 178.13 (11) | C4—C3—N2—N1 | 172.21 (10) |
C9—C10—C11—C6 | 0.8 (2) | C2—C3—N2—C5 | −154.88 (11) |
N3—C12—C13—C18 | −5.38 (17) | C4—C3—N2—C5 | 23.98 (17) |
N3—C12—C13—C14 | 174.01 (10) | C1—N1—N2—C3 | 7.89 (12) |
C18—C13—C14—C15 | 0.73 (17) | C6—N1—N2—C3 | 152.83 (10) |
C12—C13—C14—C15 | −178.67 (10) | C1—N1—N2—C5 | 159.07 (10) |
C13—C14—C15—C16 | −0.31 (17) | C6—N1—N2—C5 | −55.98 (14) |
C14—C15—C16—C17 | −0.33 (17) | C13—C12—N3—C2 | −176.14 (10) |
C14—C15—C16—C19 | 178.99 (11) | C3—C2—N3—C12 | 178.95 (11) |
C15—C16—C17—C18 | 0.54 (18) | C1—C2—N3—C12 | 7.07 (18) |
C19—C16—C17—C18 | −178.76 (11) | O2—C19—O3—C20 | −0.4 (2) |
C16—C17—C18—C13 | −0.10 (18) | C16—C19—O3—C20 | 178.58 (13) |
C14—C13—C18—C17 | −0.53 (17) |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C11H13N3O | C16H19N3O3 | C17H21N3O3 | C20H25N3O3 |
Mr | 203.24 | 301.34 | 315.37 | 355.43 |
Crystal system, space group | Hexagonal, P61 | Monoclinic, P21/c | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 173 | 173 | 173 | 173 |
a, b, c (Å) | 7.4519 (1), 7.4519 (1), 31.8705 (7) | 11.2061 (14), 7.4638 (8), 19.044 (2) | 13.427 (2), 10.1086 (14), 12.2801 (18) | 7.3857 (2), 9.2159 (3), 13.7494 (4) |
α, β, γ (°) | 90, 90, 120 | 90, 106.655 (4), 90 | 90, 101.690 (5), 90 | 85.898 (1), 84.499 (1), 85.210 (1) |
V (Å3) | 1532.69 (5) | 1526.0 (3) | 1632.2 (4) | 926.40 (5) |
Z | 6 | 4 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 | 0.09 | 0.09 |
Crystal size (mm) | 0.45 × 0.18 × 0.15 | 0.42 × 0.33 × 0.13 | 0.42 × 0.39 × 0.31 | 0.3 × 0.3 × 0.19 |
Data collection | ||||
Diffractometer | Bruker D8 Venture Photon CMOS diffractometer | Bruker D8 Venture Photon diffractometer | Bruker D8 Venture Photon diffractometer | Bruker D8 Venture Photon diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.95, 0.96 | 0.96, 0.99 | 0.96, 0.97 | 0.95, 0.96 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13962, 2455, 2353 | 12126, 3670, 3114 | 20796, 3921, 3494 | 20559, 4466, 3628 |
Rint | 0.031 | 0.018 | 0.021 | 0.043 |
(sin θ/λ)max (Å−1) | 0.660 | 0.660 | 0.661 | 0.660 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.083, 1.07 | 0.039, 0.108, 1.04 | 0.040, 0.115, 1.04 | 0.039, 0.107, 1.04 |
No. of reflections | 2455 | 3670 | 3921 | 4466 |
No. of parameters | 147 | 207 | 216 | 242 |
No. of restraints | 1 | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.15 | 0.32, −0.25 | 0.30, −0.26 | 0.24, −0.23 |
Absolute structure | Flack x determined using 1076 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013). | ? | ? | ? |
Absolute structure parameter | 0.2 (10) | ? | ? | ? |
(V) | (VI) | (VII) | |
Crystal data | |||
Chemical formula | C22H23N3O3 | C14H14N4O2 | C20H19N3O3 |
Mr | 377.43 | 270.29 | 349.38 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, C2/c |
Temperature (K) | 173 | 173 | 173 |
a, b, c (Å) | 8.4851 (7), 12.4253 (10), 18.0314 (18) | 6.9996 (8), 12.3350 (16), 15.8345 (19) | 32.7563 (10), 6.9258 (2), 16.4002 (5) |
α, β, γ (°) | 90, 92.282 (3), 90 | 90, 99.666 (4), 90 | 90, 106.032 (1), 90 |
V (Å3) | 1899.5 (3) | 1347.7 (3) | 3575.90 (19) |
Z | 4 | 4 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.09 | 0.09 |
Crystal size (mm) | 0.44 × 0.34 × 0.11 | 0.67 × 0.16 × 0.11 | 0.68 × 0.24 × 0.09 |
Data collection | |||
Diffractometer | Bruker D8 Venture Photon diffractometer | Bruker D8 Venture Photon diffractometer | Bruker D8 Venture Photon diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.95, 0.96 | 0.98, 0.99 | 0.95, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28673, 4570, 3838 | 19472, 3252, 2737 | 31732, 4312, 3539 |
Rint | 0.025 | 0.023 | 0.040 |
(sin θ/λ)max (Å−1) | 0.660 | 0.660 | 0.660 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.095, 1.04 | 0.036, 0.097, 1.03 | 0.040, 0.110, 1.03 |
No. of reflections | 4570 | 3252 | 4312 |
No. of parameters | 260 | 187 | 238 |
No. of restraints | 0 | 0 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.19 | 0.27, −0.18 | 0.24, −0.30 |
Absolute structure | ? | ? | ? |
Absolute structure parameter | ? | ? | ? |
Computer programs: APEX3 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SAINT-Plus (Bruker 2007), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O1i | 0.86 (4) | 2.15 (4) | 2.999 (3) | 170 (3) |
Symmetry code: (i) x−y, x−1, z+1/6. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.865 (15) | 2.048 (16) | 2.7312 (13) | 135 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.886 (18) | 2.009 (18) | 2.7192 (12) | 136 (1) |
C11—H11···O1i | 0.95 | 2.35 | 3.2829 (14) | 167 |
C8—H8···O3ii | 0.95 | 2.7 | 3.6206 (15) | 164 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.896 (16) | 1.934 (16) | 2.6618 (13) | 137 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.867 (16) | 2.224 (15) | 2.8413 (13) | 128 (1) |
N3—H3···O2i | 0.867 (16) | 2.404 (16) | 3.1590 (14) | 146 (1) |
C8—H8···O1ii | 0.95 | 2.6 | 3.5462 (15) | 176 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O1i | 0.903 (15) | 1.884 (15) | 2.7835 (12) | 174 (1) |
C9—H9···O2ii | 0.95 | 2.55 | 3.4485 (16) | 157 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1 | 0.95 | 2.37 | 3.0486 (17) | 128 |