research communications
Crystal structures of N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylamine and N,N-dimethyl-(2-(2,2-diphenyl)-2-prop-2-ynyloxy)acetoxy)ethylammonium 2,4,6-trinitrophenolate
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India, bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, cMaterials Science Center, NCHS Building, University of Mysore, Manasagangotri, Mysuru 570 006, India, and dSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
*Correspondence e-mail: yathirajan@hotmail.com
The N,N-dimethylethylamminium unit in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylamine, C21H23NO3 (I), is disordered over two sets of atomic sites having occupancies of 0.880 (3) and 0. 120 (3), but there are no direction-specific interactions between the molecules of (I). The cation in N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylammonium 2,4,6-trinitrophenolate (picrate), C21H24NO3+·C6H2N3O7− (II), shows a similar type of disorder, with occupancies of 0.654 (11) and 0.346 (11), although the overall conformation of the cation in (II) is different from that in the neutral (I). The component ions are are linked by an almost planar three-centre N—H⋯(O)2 hydrogen bond, and the ion pairs are further linked by a combination of three C—H⋯O hydrogen bonds to form sheets. Comparisons are made with some related structures.
Keywords: crystal structure; disorder; molecular conformation; hydrogen bonding.
1. Chemical context
N,N-dimethyl-[2-(2,2-diphenyl)-2-prop-2-ynyloxyacetoxy]ethylamine (pargeverine) is an established anti-spasmodic drug (Mishra et al., 2010). Although crystal structures have been reported (Bindya et al., 2007; Harrison, Bindya et al., 2007; Harrison, Sreevidya et al., 2007; Swamy et al., 2007; Yathirajan et al., 2007; Jasinski et al., 2009) for a number of related compounds that exhibit a range of pharmacological activities (e.g. Matsushima et al., 1997), the structure of pargeverine itself has not yet been reported. Here we report the structure of the neutral compound (I) and its 2,4,6-trinitrophenolate (picrate) salt (II).
2. Structural commentary
In the neutral compound (I) (Fig. 1) the methylaminoethyl fragment is disordered over two sets of atomic sites with occupancies of 0.880 (3) for the major disorder component comprising the atomic sites C2,C1,N1,C111 and C112, and 0.120 (3) for the minor component, comprising the atomic sites C22,C21,N21,C211 and C212. The atomic sites in the two disorder components exhibit an approximately mirror-image relationship, as shown by the corresponding pairs of torsional angles, thus: O11—C2—C1—N1 = 59.5 (5)° and O11—C22—C21—N21 = −57 (3)°, C2—C1—N1—C111 = 68.9 (4)° and C22—C21—N21—C211 = −56 (2)°, and C2—C1—N1—C112 = −167.3 (4)° and C22—C21—N21—C212 = −180 (2)°. Exact, though nonetheless would require that the corresponding torsional angles have identical magnitudes, but opposite signs. An unexpected feature of this is the close proximity of the two sites N1 and N21, which are separated by only 0.182 (18) Å.
In the cation of the picrate salt (II) (Fig. 2), the same fragment is disordered, again over two sets of atomic sites, but now with occupancies of 0.654 (11) and 0.346 (11). The physical separation of the two sets of atomic sites is, in general, rather less in (II) than in (I), but the overall conformation of the cation in (II) is different from that of the neutral compound (I). This is well illustrated by the values of the torsion angles O12—C11—C12—O13, 157.8 (2)° in (I) and 13.1 (2)° in (II), and C11—O11—C2—C1 − 123.1 (4)° in (I) and 172.8 (4)° in (II), resulting in very different locations for the disordered fragment relative to the fragment Ph2COCH2CCH (cf. Figs. 1 and 2).
The C—O distance in the picrate anion in (II), 1.2486 (17) Å, is short for its type [mean value (Allen et al., 1987) 1.362 Å, lower quartile value 1.353 Å]; the C—N distances in this anion, in the range 1.445 (2)–1.459 (2) Å, all fall below the mean value of 1.468 Å for bonds of this type. In addition, the C31—C32 and C31—C36 distances are 1.445 (2) and 1.439 (2) Å, respectively, whereas the other four C—C distances in this ring lie in the range 1.367 (2)–1.385 (2) Å with a mean value of 1.375 Å. These observations point to significant contributions to the electronic structure of this anion of polarized forms in which the negative charge is delocalized from the phenolic O atom into the ring and thence onto the nitro groups as recently noted (Sagar et al., 2017).
3. Supramolecular features
Despite the abundance of potential hydrogen-bond donors and acceptors in (I), with the C—H bonds of the aryl rings and the alkynyl unit as potential donors, and the amino N atom, the carbonyl O atom, two aryl rings and the triple bond of the alkynyl function as potential acceptors, there are in fact, no hydrogen bonds of any kind in the of (I): nor are there any aromatic π–π stacking interactions, so that the structure consists of essentially isolated molecules making only van der Waals-type contacts with one another.
Both disorder components of the cation in (II) are linked to the anion within the selected via a near planar, but markedly asymmetric three-centre N-H⋯(O)2 charge-assisted (Gilli et al., 1994) hydrogen bond (Table 1), which forms an R12(6) motif. The resulting ion pairs are further linked by three C—H⋯O hydrogen bonds into complex sheets: however, the straightforward identification of two simple one-dimensional sub-structures (Ferguson et al., 1998a,b; Gregson et al., 2000) leads to a simple analysis of the sheet formation. In the simpler of the two sub-structures, the C—H⋯O hydrogen bond involving an aryl C—H unit links ion pairs related by translation along [100] into a C21(12) chain (Fig. 3). In the second sub-structure, the cooperative effect of two C—H⋯O hydrogen bonds, both involving CH2 groups, generates a chain parallel to [10] containing alternating R12(6) and R22(11) rings (Fig. 4). The combination of these two chain motifs generates a sheet lying parallel to (001) in the domain 0.5 < z < 1.0: a second such sheet, related to the first by inversion, lies in the domain 0 < z < 0.5, but there are no direction-specific interactions between adjacent sheets.
4. Database survey
In the (2R,3R)-(hydrogentartrate) salt (III) (Glidewell et al., 2017), the cation is fully ordered, unlike that in the picrate (II) and the conformation of the cation closely resembles that of the neutral molecule (I).
The anions are linked by three O—H⋯O hydrogen bonds to form sheets lying parallel to (001) and containing equal numbers of R22(7) and R44(21) rings (Fig. 5). Within this sheet, the anions related by translation along [100] are linked by a very short and nearly linear O—H⋯O hydrogen bond, although the H atom is nonetheless off-centre; O⋯Oi 2.461 (7) Å; O—H⋯Oi 167 (9)°, O—H 1.12 (1) Å, H⋯Oi 1.35 (10) Å [symmetry code: (i) 1 + x, y, z]. The cations are linked to this sheet by a three-centre N—O⋯(O)2 hydrogen bond and they are disposed to either side of the sheet (Fig. 6).
4-(2,2-Diphenyl-2-propoxyacetoxy)-1-methylpiperidin-1-ium picrate (propiverinium picrate) (IV) is closely related to compound (II), differing in containing a saturated alkoxy substituent and having an N-methyl piperidinium unit in place of the N,N-dimethylethylammonium unit in (II). The component anions in (IV) are linked (Jasinski et al., 2009) by the same type of hydrogen-bonded (R126) ring as seen in (II) but there are no structurally significant interactions between adjacent ion pairs in (IV).
5. Synthesis and crystallization
A sample of compound (I) was a gift from RL Fine Chem, Pvt. Ltd., Bengaluru, India, and it was recrystallized from methanol solution by slow evaporation at room temperature, m.p. 347–351 K. For the preparation of compound (II), equimolar quantities (0.30 mmol) of (I) and picric acid were dissolved in hot methanol and the solution was held at 333 K for 0.5 h, with magnetic stirring throughout. The solution was then allowed to cool slowly to room temperature, giving crystals of (II) suitable for single-crystal X-ray diffraction. m.p. 386–389 K.
6. Refinement
Crystal data, data collection and structure . It was apparent from an early stage in the refinements that in both (I) and (II) the dimethylaminoethyl portion was disordered over two sets of atomic sites having different occupancies in each case, and corresponding to different conformations. For the minor conformation of each compound, the bonded distances and the 1,3-non-bonded distances were restrained to be the same as the corresponding distances in the major conformer, subject to s.u.s of 0.005 and 0.01 Å, respectively: in addition, the anisotropic displacement parameters for corresponding pairs of atomic sites occupying essentially the same physical space were constrained to be equal. All H atoms, other than those in the minor disorder components, were located in difference maps, and then treated as riding atoms in geometrically idealized position, with distances C—H 0.93 Å (aromatic and alkyne), 0.96 Å (CH3) or 0.97 Å (CH2) and N—H 0.98 Å, with Uiso(H) = kUeq(carrier), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and 1.2 for all other H atoms. The H atoms in the minor disorder components were included in calculated positions using the same procedure. When the of the atomic coordinates for the H atoms bonded to N atoms in (II) was attempted, the resulting N—H distances were 1.04 (4) and 0.82 (8) Å: accordingly, the riding model was preferred. Two low-angle reflections which had been attenuated by the beam stop, (020) for (I) and (002) for (II), were omitted from the final refinements. Subject to these conditions, the occupancies of the disorder components were 0.880 (3) and 0.120 (3) in (I) and 0.654 (11) and 0.346 (11) in (II). In the final analyses of variance for (I) there was a large value, 22.969, of K = [mean(Fo2)/mean(Fc2)] for the group of 518 very weak reflections having Fc/Fc(max) in the range 0.000 < Fc/Fc(max) < 0.004, and for (II) a value of K = 9.509 for the group of 789 very weak reflections having Fc/Fc(max) in the range 0.000 < Fc/Fc(max) < 0.006.
details are summarized in Table 2
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Supporting information
https://doi.org/10.1107/S2056989017012968/bq2403sup1.cif
contains datablocks global, I, II. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017012968/bq2403Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989017012968/bq2403IIsup3.hkl
For both structures, data collection: CrystalClear (Rigaku, 2011); cell
CrystalClear (Rigaku, 2011); data reduction: CrystalClear (Rigaku, 2011); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).C21H23NO3 | F(000) = 720 |
Mr = 337.40 | Dx = 1.183 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2545 (9) Å | Cell parameters from 5622 reflections |
b = 21.7246 (19) Å | θ = 1.9–31.2° |
c = 9.4531 (9) Å | µ = 0.08 mm−1 |
β = 94.763 (9)° | T = 296 K |
V = 1894.0 (3) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.24 × 0.23 mm |
Rigaku Saturn724 diffractometer | 2221 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.066 |
φ and ω scans | θmax = 27.6°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick,2003) | h = −9→11 |
Tmin = 0.956, Tmax = 0.982 | k = −28→28 |
23094 measured reflections | l = −12→12 |
4348 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.064 | w = 1/[σ2(Fo2) + (0.0758P)2 + 0.2089P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.195 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.16 e Å−3 |
4348 reflections | Δρmin = −0.15 e Å−3 |
247 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
10 restraints | Extinction coefficient: 0.011 (2) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.1191 (3) | 0.41234 (15) | 0.8098 (3) | 0.0714 (6) | 0.880 (3) |
C111 | 0.2407 (5) | 0.37948 (19) | 0.7606 (5) | 0.1196 (16) | 0.880 (3) |
H11A | 0.3275 | 0.4032 | 0.7805 | 0.179* | 0.880 (3) |
H11B | 0.2247 | 0.3728 | 0.6602 | 0.179* | 0.880 (3) |
H11C | 0.2509 | 0.3405 | 0.8084 | 0.179* | 0.880 (3) |
C112 | −0.0119 (5) | 0.3773 (2) | 0.7788 (5) | 0.1315 (16) | 0.880 (3) |
H11D | −0.0068 | 0.3400 | 0.8336 | 0.197* | 0.880 (3) |
H11E | −0.0224 | 0.3673 | 0.6796 | 0.197* | 0.880 (3) |
H11F | −0.0937 | 0.4011 | 0.8026 | 0.197* | 0.880 (3) |
C1 | 0.1396 (3) | 0.42760 (13) | 0.9570 (3) | 0.0735 (9) | 0.880 (3) |
H1A | 0.1655 | 0.3906 | 1.0107 | 0.088* | 0.880 (3) |
H1B | 0.0488 | 0.4427 | 0.9880 | 0.088* | 0.880 (3) |
C2 | 0.2551 (7) | 0.47531 (13) | 0.9896 (4) | 0.0849 (9) | 0.880 (3) |
H2A | 0.2646 | 0.4840 | 1.0906 | 0.102* | 0.880 (3) |
H2B | 0.3476 | 0.4602 | 0.9627 | 0.102* | 0.880 (3) |
O11 | 0.21492 (17) | 0.53133 (7) | 0.91034 (17) | 0.0686 (5) | 0.880 (3) |
N21 | 0.1334 (19) | 0.4120 (9) | 0.8101 (19) | 0.0714 (6) | 0.120 (3) |
C212 | 0.143 (3) | 0.3597 (14) | 0.718 (3) | 0.1196 (16) | 0.120 (3) |
H21A | 0.2189 | 0.3663 | 0.6562 | 0.179* | 0.120 (3) |
H21B | 0.0523 | 0.3545 | 0.6614 | 0.179* | 0.120 (3) |
H21C | 0.1634 | 0.3233 | 0.7734 | 0.179* | 0.120 (3) |
C211 | 0.012 (2) | 0.4041 (15) | 0.895 (3) | 0.1315 (16) | 0.120 (3) |
H21D | −0.0293 | 0.3640 | 0.8779 | 0.197* | 0.120 (3) |
H21E | −0.0593 | 0.4350 | 0.8703 | 0.197* | 0.120 (3) |
H21F | 0.0452 | 0.4079 | 0.9938 | 0.197* | 0.120 (3) |
C21 | 0.2645 (18) | 0.4226 (5) | 0.897 (2) | 0.0735 (9) | 0.120 (3) |
H21G | 0.3427 | 0.4295 | 0.8369 | 0.088* | 0.120 (3) |
H21H | 0.2879 | 0.3861 | 0.9536 | 0.088* | 0.120 (3) |
C22 | 0.255 (5) | 0.4768 (5) | 0.9950 (18) | 0.0849 (9) | 0.120 (3) |
H22A | 0.1833 | 0.4690 | 1.0619 | 0.102* | 0.120 (3) |
H22B | 0.3482 | 0.4833 | 1.0483 | 0.102* | 0.120 (3) |
O21 | 0.21492 (17) | 0.53133 (7) | 0.91034 (17) | 0.0686 (5) | 0.120 (3) |
C11 | 0.3078 (3) | 0.55286 (10) | 0.8243 (2) | 0.0560 (6) | |
O12 | 0.42714 (18) | 0.53231 (8) | 0.81288 (19) | 0.0774 (6) | |
C12 | 0.2500 (2) | 0.61174 (9) | 0.7481 (2) | 0.0519 (5) | |
O13 | 0.09551 (14) | 0.61353 (6) | 0.73420 (15) | 0.0549 (4) | |
C14 | 0.0256 (2) | 0.56650 (10) | 0.6483 (2) | 0.0603 (6) | |
H14A | 0.0515 | 0.5263 | 0.6874 | 0.072* | |
H14B | 0.0563 | 0.5686 | 0.5528 | 0.072* | |
C15 | −0.1296 (3) | 0.57546 (11) | 0.6453 (2) | 0.0603 (6) | |
C16 | −0.2545 (3) | 0.58165 (14) | 0.6416 (3) | 0.0869 (9) | |
H16 | −0.3545 | 0.5866 | 0.6386 | 0.104* | |
C121 | 0.3093 (2) | 0.61909 (10) | 0.6028 (2) | 0.0538 (6) | |
C122 | 0.3424 (2) | 0.56994 (11) | 0.5191 (3) | 0.0654 (7) | |
H122 | 0.3367 | 0.5301 | 0.5543 | 0.079* | |
C123 | 0.3841 (3) | 0.57906 (14) | 0.3833 (3) | 0.0804 (8) | |
H123 | 0.4062 | 0.5454 | 0.3283 | 0.096* | |
C124 | 0.3928 (3) | 0.63714 (17) | 0.3298 (3) | 0.0898 (9) | |
H124 | 0.4213 | 0.6431 | 0.2388 | 0.108* | |
C125 | 0.3594 (3) | 0.68648 (15) | 0.4108 (3) | 0.0889 (9) | |
H125 | 0.3638 | 0.7261 | 0.3740 | 0.107* | |
C126 | 0.3192 (3) | 0.67781 (12) | 0.5471 (3) | 0.0725 (7) | |
H126 | 0.2986 | 0.7117 | 0.6019 | 0.087* | |
C131 | 0.2994 (2) | 0.66400 (10) | 0.8497 (2) | 0.0571 (6) | |
C132 | 0.4459 (3) | 0.67502 (12) | 0.8790 (3) | 0.0843 (8) | |
H132 | 0.5132 | 0.6509 | 0.8365 | 0.101* | |
C133 | 0.4930 (4) | 0.72146 (15) | 0.9706 (3) | 0.0987 (10) | |
H133 | 0.5918 | 0.7288 | 0.9889 | 0.118* | |
C134 | 0.3965 (4) | 0.75646 (13) | 1.0342 (3) | 0.0952 (10) | |
H134 | 0.4289 | 0.7876 | 1.0966 | 0.114* | |
C135 | 0.2507 (4) | 0.74606 (13) | 1.0068 (3) | 0.0933 (9) | |
H135 | 0.1843 | 0.7704 | 1.0498 | 0.112* | |
C136 | 0.2019 (3) | 0.69943 (11) | 0.9152 (3) | 0.0730 (7) | |
H136 | 0.1030 | 0.6921 | 0.8980 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0713 (16) | 0.0745 (13) | 0.0683 (14) | 0.0059 (11) | 0.0060 (11) | 0.0046 (10) |
C111 | 0.122 (4) | 0.109 (3) | 0.135 (4) | 0.016 (3) | 0.047 (3) | −0.014 (3) |
C112 | 0.108 (3) | 0.154 (4) | 0.126 (4) | −0.034 (3) | −0.028 (3) | −0.019 (3) |
C1 | 0.079 (2) | 0.0749 (18) | 0.0674 (19) | −0.0072 (15) | 0.0104 (15) | 0.0114 (14) |
C2 | 0.097 (2) | 0.0824 (18) | 0.0710 (18) | −0.0109 (15) | −0.0182 (15) | 0.0298 (14) |
O11 | 0.0646 (11) | 0.0706 (10) | 0.0701 (11) | −0.0038 (8) | 0.0022 (8) | 0.0146 (8) |
N21 | 0.0713 (16) | 0.0745 (13) | 0.0683 (14) | 0.0059 (11) | 0.0060 (11) | 0.0046 (10) |
C212 | 0.122 (4) | 0.109 (3) | 0.135 (4) | 0.016 (3) | 0.047 (3) | −0.014 (3) |
C211 | 0.108 (3) | 0.154 (4) | 0.126 (4) | −0.034 (3) | −0.028 (3) | −0.019 (3) |
C21 | 0.079 (2) | 0.0749 (18) | 0.0674 (19) | −0.0072 (15) | 0.0104 (15) | 0.0114 (14) |
C22 | 0.097 (2) | 0.0824 (18) | 0.0710 (18) | −0.0109 (15) | −0.0182 (15) | 0.0298 (14) |
O21 | 0.0646 (11) | 0.0706 (10) | 0.0701 (11) | −0.0038 (8) | 0.0022 (8) | 0.0146 (8) |
C11 | 0.0462 (14) | 0.0603 (13) | 0.0602 (14) | −0.0003 (11) | −0.0033 (11) | −0.0009 (11) |
O12 | 0.0573 (12) | 0.0861 (12) | 0.0880 (13) | 0.0196 (9) | 0.0010 (9) | 0.0147 (9) |
C12 | 0.0402 (13) | 0.0560 (12) | 0.0589 (13) | 0.0006 (9) | 0.0005 (10) | 0.0000 (10) |
O13 | 0.0403 (9) | 0.0568 (9) | 0.0667 (10) | 0.0001 (6) | −0.0008 (7) | −0.0052 (7) |
C14 | 0.0474 (14) | 0.0655 (14) | 0.0664 (15) | −0.0069 (10) | −0.0039 (11) | −0.0062 (11) |
C15 | 0.0486 (15) | 0.0732 (15) | 0.0586 (14) | −0.0082 (11) | 0.0019 (11) | 0.0039 (11) |
C16 | 0.0495 (17) | 0.114 (2) | 0.096 (2) | −0.0066 (15) | 0.0000 (14) | −0.0089 (17) |
C121 | 0.0366 (12) | 0.0597 (13) | 0.0647 (14) | 0.0012 (9) | 0.0015 (10) | 0.0031 (11) |
C122 | 0.0579 (15) | 0.0708 (15) | 0.0680 (16) | 0.0038 (11) | 0.0078 (12) | 0.0023 (12) |
C123 | 0.0661 (18) | 0.104 (2) | 0.0729 (18) | 0.0116 (15) | 0.0140 (13) | −0.0018 (16) |
C124 | 0.072 (2) | 0.125 (3) | 0.0751 (19) | 0.0081 (17) | 0.0218 (15) | 0.0191 (19) |
C125 | 0.082 (2) | 0.090 (2) | 0.095 (2) | −0.0066 (16) | 0.0172 (17) | 0.0297 (18) |
C126 | 0.0689 (17) | 0.0704 (16) | 0.0783 (18) | 0.0006 (12) | 0.0058 (13) | 0.0116 (13) |
C131 | 0.0549 (15) | 0.0526 (12) | 0.0626 (14) | −0.0033 (10) | −0.0025 (11) | 0.0016 (10) |
C132 | 0.0567 (17) | 0.0823 (18) | 0.111 (2) | −0.0084 (13) | −0.0133 (15) | −0.0131 (16) |
C133 | 0.087 (2) | 0.088 (2) | 0.115 (3) | −0.0243 (18) | −0.0298 (19) | −0.0037 (19) |
C134 | 0.133 (3) | 0.0632 (17) | 0.083 (2) | −0.0200 (19) | −0.029 (2) | −0.0020 (14) |
C135 | 0.115 (3) | 0.0709 (18) | 0.093 (2) | −0.0019 (17) | 0.0038 (19) | −0.0187 (15) |
C136 | 0.0724 (17) | 0.0671 (15) | 0.0790 (17) | −0.0037 (13) | 0.0039 (14) | −0.0103 (13) |
N1—C1 | 1.428 (4) | C12—O13 | 1.426 (2) |
N1—C112 | 1.442 (5) | C12—C121 | 1.529 (3) |
N1—C111 | 1.442 (4) | C12—C131 | 1.532 (3) |
C111—H11A | 0.9600 | O13—C14 | 1.426 (2) |
C111—H11B | 0.9600 | C14—C15 | 1.447 (3) |
C111—H11C | 0.9600 | C14—H14A | 0.9700 |
C112—H11D | 0.9600 | C14—H14B | 0.9700 |
C112—H11E | 0.9600 | C15—C16 | 1.161 (3) |
C112—H11F | 0.9600 | C16—H16 | 0.9300 |
C1—C2 | 1.502 (6) | C121—C122 | 1.378 (3) |
C1—H1A | 0.9700 | C121—C126 | 1.386 (3) |
C1—H1B | 0.9700 | C122—C123 | 1.385 (3) |
C2—O11 | 1.461 (3) | C122—H122 | 0.9300 |
C2—H2A | 0.9700 | C123—C124 | 1.364 (4) |
C2—H2B | 0.9700 | C123—H123 | 0.9300 |
O11—C11 | 1.317 (3) | C124—C125 | 1.367 (4) |
N21—C21 | 1.428 (6) | C124—H124 | 0.9300 |
N21—C211 | 1.441 (7) | C125—C126 | 1.384 (3) |
N21—C212 | 1.442 (6) | C125—H125 | 0.9300 |
C212—H21A | 0.9600 | C126—H126 | 0.9300 |
C212—H21B | 0.9600 | C131—C136 | 1.372 (3) |
C212—H21C | 0.9600 | C131—C132 | 1.382 (3) |
C211—H21D | 0.9600 | C132—C133 | 1.377 (4) |
C211—H21E | 0.9600 | C132—H132 | 0.9300 |
C211—H21F | 0.9600 | C133—C134 | 1.352 (4) |
C21—C22 | 1.503 (8) | C133—H133 | 0.9300 |
C21—H21G | 0.9700 | C134—C135 | 1.371 (4) |
C21—H21H | 0.9700 | C134—H134 | 0.9300 |
C22—H22A | 0.9700 | C135—C136 | 1.384 (3) |
C22—H22B | 0.9700 | C135—H135 | 0.9300 |
C11—O12 | 1.204 (2) | C136—H136 | 0.9300 |
C11—C12 | 1.542 (3) | ||
C1—N1—C112 | 111.3 (3) | O12—C11—C12 | 123.4 (2) |
C1—N1—C111 | 112.7 (3) | O11—C11—C12 | 111.37 (19) |
C112—N1—C111 | 109.8 (4) | O13—C12—C121 | 110.28 (16) |
N1—C111—H11A | 109.5 | O13—C12—C131 | 106.39 (16) |
N1—C111—H11B | 109.5 | C121—C12—C131 | 112.03 (17) |
H11A—C111—H11B | 109.5 | O13—C12—C11 | 111.83 (17) |
N1—C111—H11C | 109.5 | C121—C12—C11 | 111.72 (17) |
H11A—C111—H11C | 109.5 | C131—C12—C11 | 104.35 (17) |
H11B—C111—H11C | 109.5 | C12—O13—C14 | 115.91 (15) |
N1—C112—H11D | 109.5 | O13—C14—C15 | 108.50 (18) |
N1—C112—H11E | 109.5 | O13—C14—H14A | 110.0 |
H11D—C112—H11E | 109.5 | C15—C14—H14A | 110.0 |
N1—C112—H11F | 109.5 | O13—C14—H14B | 110.0 |
H11D—C112—H11F | 109.5 | C15—C14—H14B | 110.0 |
H11E—C112—H11F | 109.5 | H14A—C14—H14B | 108.4 |
N1—C1—C2 | 113.3 (3) | C16—C15—C14 | 178.7 (3) |
N1—C1—H1A | 108.9 | C15—C16—H16 | 180.0 |
C2—C1—H1A | 108.9 | C122—C121—C126 | 118.0 (2) |
N1—C1—H1B | 108.9 | C122—C121—C12 | 123.23 (19) |
C2—C1—H1B | 108.9 | C126—C121—C12 | 118.5 (2) |
H1A—C1—H1B | 107.7 | C121—C122—C123 | 120.9 (2) |
O11—C2—C1 | 108.8 (3) | C121—C122—H122 | 119.6 |
O11—C2—H2A | 109.9 | C123—C122—H122 | 119.6 |
C1—C2—H2A | 109.9 | C124—C123—C122 | 120.4 (3) |
O11—C2—H2B | 109.9 | C124—C123—H123 | 119.8 |
C1—C2—H2B | 109.9 | C122—C123—H123 | 119.8 |
H2A—C2—H2B | 108.3 | C123—C124—C125 | 119.6 (3) |
C11—O11—C2 | 117.4 (3) | C123—C124—H124 | 120.2 |
C21—N21—C211 | 111.1 (8) | C125—C124—H124 | 120.2 |
C21—N21—C212 | 112.7 (8) | C124—C125—C126 | 120.4 (3) |
C211—N21—C212 | 109.4 (8) | C124—C125—H125 | 119.8 |
N21—C212—H21A | 109.5 | C126—C125—H125 | 119.8 |
N21—C212—H21B | 109.5 | C125—C126—C121 | 120.7 (3) |
H21A—C212—H21B | 109.5 | C125—C126—H126 | 119.6 |
N21—C212—H21C | 109.5 | C121—C126—H126 | 119.6 |
H21A—C212—H21C | 109.5 | C136—C131—C132 | 118.9 (2) |
H21B—C212—H21C | 109.5 | C136—C131—C12 | 121.7 (2) |
N21—C211—H21D | 109.5 | C132—C131—C12 | 119.4 (2) |
N21—C211—H21E | 109.5 | C133—C132—C131 | 120.5 (3) |
H21D—C211—H21E | 109.5 | C133—C132—H132 | 119.8 |
N21—C211—H21F | 109.5 | C131—C132—H132 | 119.8 |
H21D—C211—H21F | 109.5 | C134—C133—C132 | 120.4 (3) |
H21E—C211—H21F | 109.5 | C134—C133—H133 | 119.8 |
N21—C21—C22 | 113.1 (9) | C132—C133—H133 | 119.8 |
N21—C21—H21G | 109.0 | C133—C134—C135 | 120.0 (3) |
C22—C21—H21G | 109.0 | C133—C134—H134 | 120.0 |
N21—C21—H21H | 109.0 | C135—C134—H134 | 120.0 |
C22—C21—H21H | 109.0 | C134—C135—C136 | 120.2 (3) |
H21G—C21—H21H | 107.8 | C134—C135—H135 | 119.9 |
C21—C22—H22A | 109.9 | C136—C135—H135 | 119.9 |
C21—C22—H22B | 109.9 | C131—C136—C135 | 120.0 (3) |
H22A—C22—H22B | 108.3 | C131—C136—H136 | 120.0 |
O12—C11—O11 | 125.0 (2) | C135—C136—H136 | 120.0 |
C112—N1—C1—C2 | −167.3 (4) | C11—C12—C121—C126 | −153.9 (2) |
C111—N1—C1—C2 | 68.9 (4) | C126—C121—C122—C123 | −0.1 (3) |
N1—C1—C2—O11 | 59.5 (5) | C12—C121—C122—C123 | 174.4 (2) |
C1—C2—O11—C11 | −123.1 (4) | C121—C122—C123—C124 | −0.1 (4) |
C211—N21—C21—C22 | −56 (2) | C122—C123—C124—C125 | −0.3 (4) |
C212—N21—C21—C22 | −180 (2) | C123—C124—C125—C126 | 1.0 (5) |
C2—O11—C11—O12 | −5.2 (3) | C124—C125—C126—C121 | −1.3 (4) |
C2—O11—C11—C12 | 179.8 (2) | C122—C121—C126—C125 | 0.8 (4) |
O12—C11—C12—O13 | 157.8 (2) | C12—C121—C126—C125 | −174.0 (2) |
O11—C11—C12—O13 | −27.0 (2) | O13—C12—C131—C136 | 4.0 (3) |
O12—C11—C12—C121 | 33.6 (3) | C121—C12—C131—C136 | 124.6 (2) |
O11—C11—C12—C121 | −151.20 (18) | C11—C12—C131—C136 | −114.3 (2) |
O12—C11—C12—C131 | −87.6 (3) | O13—C12—C131—C132 | −177.5 (2) |
O11—C11—C12—C131 | 87.6 (2) | C121—C12—C131—C132 | −56.9 (3) |
C121—C12—O13—C14 | 61.1 (2) | C11—C12—C131—C132 | 64.2 (3) |
C131—C12—O13—C14 | −177.23 (17) | C136—C131—C132—C133 | −1.0 (4) |
C11—C12—O13—C14 | −63.9 (2) | C12—C131—C132—C133 | −179.6 (2) |
C12—O13—C14—C15 | −179.68 (16) | C131—C132—C133—C134 | 0.7 (5) |
O13—C12—C121—C122 | −93.5 (2) | C132—C133—C134—C135 | −0.5 (5) |
C131—C12—C121—C122 | 148.2 (2) | C133—C134—C135—C136 | 0.7 (4) |
C11—C12—C121—C122 | 31.6 (3) | C132—C131—C136—C135 | 1.2 (4) |
O13—C12—C121—C126 | 81.1 (2) | C12—C131—C136—C135 | 179.7 (2) |
C131—C12—C121—C126 | −37.2 (3) | C134—C135—C136—C131 | −1.0 (4) |
C21H24NO3·C6H2N3O7 | Z = 2 |
Mr = 566.52 | F(000) = 592 |
Triclinic, P1 | Dx = 1.397 Mg m−3 |
a = 7.5208 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.3919 (3) Å | Cell parameters from 4348 reflections |
c = 22.2282 (7) Å | θ = 2.4–27.6° |
α = 85.099 (3)° | µ = 0.11 mm−1 |
β = 84.294 (3)° | T = 296 K |
γ = 75.117 (3)° | Block, colourless |
V = 1346.51 (9) Å3 | 0.23 × 0.21 × 0.21 mm |
Rigaku Saturn724 diffractometer | 4973 reflections with I > 2σ(I) |
Radiation source: fine focus sealed tube | Rint = 0.033 |
φ and ω scans | θmax = 31.1°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick,2003) | h = −10→10 |
Tmin = 0.949, Tmax = 0.978 | k = −12→9 |
18671 measured reflections | l = −31→31 |
7547 independent reflections |
Refinement on F2 | 10 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0499P)2 + 0.2103P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
7547 reflections | Δρmax = 0.27 e Å−3 |
390 parameters | Δρmin = −0.22 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.6256 (10) | 0.4825 (7) | 0.6843 (3) | 0.0517 (9) | 0.654 (11) |
H1 | 0.7502 | 0.4253 | 0.6689 | 0.062* | 0.654 (11) |
C111 | 0.5676 (10) | 0.3670 (6) | 0.7326 (4) | 0.0770 (17) | 0.654 (11) |
H11A | 0.5826 | 0.2612 | 0.7166 | 0.115* | 0.654 (11) |
H11B | 0.4403 | 0.4105 | 0.7461 | 0.115* | 0.654 (11) |
H11C | 0.6424 | 0.3550 | 0.7660 | 0.115* | 0.654 (11) |
C112 | 0.5108 (16) | 0.5096 (11) | 0.6316 (3) | 0.0809 (18) | 0.654 (11) |
H11D | 0.3834 | 0.5528 | 0.6451 | 0.121* | 0.654 (11) |
H11E | 0.5252 | 0.4067 | 0.6136 | 0.121* | 0.654 (11) |
H11F | 0.5499 | 0.5870 | 0.6022 | 0.121* | 0.654 (11) |
C1 | 0.6438 (8) | 0.6401 (8) | 0.7067 (4) | 0.0500 (9) | 0.654 (11) |
H1A | 0.7169 | 0.6903 | 0.6760 | 0.060* | 0.654 (11) |
H1B | 0.7123 | 0.6133 | 0.7425 | 0.060* | 0.654 (11) |
C2 | 0.4667 (11) | 0.7662 (7) | 0.7221 (4) | 0.0448 (9) | 0.654 (11) |
H2A | 0.4931 | 0.8687 | 0.7308 | 0.054* | 0.654 (11) |
H2B | 0.3907 | 0.7882 | 0.6881 | 0.054* | 0.654 (11) |
O11 | 0.36983 (14) | 0.70288 (12) | 0.77457 (5) | 0.0435 (3) | 0.654 (11) |
N21 | 0.612 (2) | 0.4863 (14) | 0.6728 (5) | 0.0517 (9) | 0.346 (11) |
H21 | 0.7335 | 0.4177 | 0.6599 | 0.062* | 0.346 (11) |
C211 | 0.5119 (18) | 0.3703 (13) | 0.7068 (6) | 0.0770 (17) | 0.346 (11) |
H21A | 0.3918 | 0.4310 | 0.7220 | 0.115* | 0.346 (11) |
H21B | 0.5804 | 0.3152 | 0.7401 | 0.115* | 0.346 (11) |
H21C | 0.4992 | 0.2901 | 0.6803 | 0.115* | 0.346 (11) |
C212 | 0.526 (3) | 0.558 (2) | 0.6156 (6) | 0.0809 (18) | 0.346 (11) |
H21D | 0.5839 | 0.6415 | 0.5975 | 0.121* | 0.346 (11) |
H21E | 0.3966 | 0.6054 | 0.6245 | 0.121* | 0.346 (11) |
H21F | 0.5424 | 0.4720 | 0.5881 | 0.121* | 0.346 (11) |
C21 | 0.6478 (14) | 0.6122 (18) | 0.7103 (7) | 0.0500 (9) | 0.346 (11) |
H21G | 0.7460 | 0.6556 | 0.6890 | 0.060* | 0.346 (11) |
H21H | 0.6932 | 0.5566 | 0.7479 | 0.060* | 0.346 (11) |
C22 | 0.488 (2) | 0.7555 (13) | 0.7256 (7) | 0.0448 (9) | 0.346 (11) |
H22A | 0.5327 | 0.8455 | 0.7378 | 0.054* | 0.346 (11) |
H22B | 0.4187 | 0.7945 | 0.6904 | 0.054* | 0.346 (11) |
O21 | 0.36983 (14) | 0.70288 (12) | 0.77457 (5) | 0.0435 (3) | 0.346 (11) |
C11 | 0.2198 (2) | 0.81409 (17) | 0.79625 (6) | 0.0359 (3) | |
O12 | 0.16787 (16) | 0.94998 (13) | 0.77343 (5) | 0.0506 (3) | |
C12 | 0.13145 (19) | 0.74885 (17) | 0.85597 (6) | 0.0335 (3) | |
O13 | −0.04211 (13) | 0.86286 (12) | 0.87024 (4) | 0.0367 (2) | |
C14 | −0.1829 (2) | 0.8619 (2) | 0.83189 (8) | 0.0481 (4) | |
H14A | −0.2176 | 0.7577 | 0.8386 | 0.058* | |
H14B | −0.1365 | 0.8725 | 0.7898 | 0.058* | |
C15 | −0.3429 (2) | 0.9967 (2) | 0.84437 (7) | 0.0472 (4) | |
C16 | −0.4802 (3) | 1.0991 (3) | 0.85172 (10) | 0.0723 (6) | |
H16 | −0.5894 | 1.1806 | 0.8576 | 0.087* | |
C121 | 0.25642 (19) | 0.75762 (17) | 0.90515 (6) | 0.0348 (3) | |
C122 | 0.2015 (2) | 0.87452 (19) | 0.94821 (7) | 0.0421 (4) | |
H122 | 0.0868 | 0.9497 | 0.9473 | 0.051* | |
C123 | 0.3161 (3) | 0.8801 (2) | 0.99240 (8) | 0.0543 (4) | |
H123 | 0.2772 | 0.9580 | 1.0214 | 0.065* | |
C124 | 0.4869 (3) | 0.7715 (3) | 0.99388 (9) | 0.0593 (5) | |
H124 | 0.5638 | 0.7762 | 1.0236 | 0.071* | |
C125 | 0.5439 (2) | 0.6557 (2) | 0.95124 (9) | 0.0568 (5) | |
H125 | 0.6600 | 0.5826 | 0.9519 | 0.068* | |
C126 | 0.4292 (2) | 0.6476 (2) | 0.90731 (8) | 0.0471 (4) | |
H126 | 0.4680 | 0.5678 | 0.8790 | 0.056* | |
C131 | 0.1025 (2) | 0.57518 (17) | 0.85444 (6) | 0.0357 (3) | |
C132 | 0.0746 (2) | 0.48827 (19) | 0.90896 (7) | 0.0443 (4) | |
H132 | 0.0871 | 0.5313 | 0.9451 | 0.053* | |
C133 | 0.0288 (3) | 0.3393 (2) | 0.91052 (8) | 0.0537 (4) | |
H133 | 0.0097 | 0.2832 | 0.9475 | 0.064* | |
C134 | 0.0110 (3) | 0.2730 (2) | 0.85755 (9) | 0.0540 (4) | |
H134 | −0.0201 | 0.1724 | 0.8587 | 0.065* | |
C135 | 0.0395 (2) | 0.3566 (2) | 0.80287 (8) | 0.0497 (4) | |
H135 | 0.0295 | 0.3116 | 0.7669 | 0.060* | |
C136 | 0.0830 (2) | 0.50791 (19) | 0.80123 (7) | 0.0424 (4) | |
H136 | 0.0994 | 0.5648 | 0.7642 | 0.051* | |
C31 | 1.0191 (2) | 0.18823 (19) | 0.61774 (7) | 0.0424 (4) | |
O31 | 0.93492 (18) | 0.25416 (15) | 0.66415 (5) | 0.0584 (3) | |
C32 | 1.0549 (2) | 0.01354 (19) | 0.60957 (7) | 0.0426 (4) | |
N32 | 0.9763 (2) | −0.08842 (19) | 0.65583 (6) | 0.0529 (4) | |
O32 | 0.8237 (2) | −0.03049 (19) | 0.68053 (7) | 0.0753 (4) | |
O33 | 1.0676 (2) | −0.22946 (16) | 0.66751 (6) | 0.0688 (4) | |
C33 | 1.1556 (2) | −0.0640 (2) | 0.56099 (7) | 0.0450 (4) | |
H33 | 1.1750 | −0.1773 | 0.5585 | 0.054* | |
C34 | 1.2283 (2) | 0.0300 (2) | 0.51549 (7) | 0.0435 (4) | |
N34 | 1.3347 (2) | −0.0478 (2) | 0.46332 (7) | 0.0558 (4) | |
O34 | 1.3586 (2) | −0.19701 (19) | 0.46114 (7) | 0.0872 (5) | |
O35 | 1.3986 (2) | 0.0377 (2) | 0.42408 (6) | 0.0740 (4) | |
C35 | 1.2027 (2) | 0.1978 (2) | 0.51881 (7) | 0.0438 (4) | |
H35 | 1.2539 | 0.2590 | 0.4882 | 0.053* | |
C36 | 1.1010 (2) | 0.27324 (19) | 0.56788 (7) | 0.0429 (4) | |
N36 | 1.0748 (2) | 0.45097 (18) | 0.56790 (7) | 0.0525 (4) | |
O36 | 1.1884 (2) | 0.51340 (17) | 0.53894 (7) | 0.0749 (4) | |
O37 | 0.9371 (2) | 0.53363 (16) | 0.59497 (7) | 0.0786 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0486 (13) | 0.0446 (9) | 0.057 (2) | −0.0052 (9) | 0.0087 (16) | −0.0119 (13) |
C111 | 0.074 (4) | 0.0484 (13) | 0.099 (4) | −0.012 (2) | 0.027 (3) | −0.006 (3) |
C112 | 0.080 (2) | 0.080 (5) | 0.082 (4) | −0.004 (3) | −0.015 (4) | −0.038 (3) |
C1 | 0.0448 (9) | 0.050 (2) | 0.0532 (12) | −0.0107 (12) | 0.0077 (9) | −0.0113 (16) |
C2 | 0.048 (2) | 0.0416 (11) | 0.0435 (12) | −0.0126 (11) | 0.0092 (14) | −0.0078 (8) |
O11 | 0.0461 (6) | 0.0387 (6) | 0.0399 (5) | −0.0045 (5) | 0.0090 (5) | −0.0042 (4) |
N21 | 0.0486 (13) | 0.0446 (9) | 0.057 (2) | −0.0052 (9) | 0.0087 (16) | −0.0119 (13) |
C211 | 0.074 (4) | 0.0484 (13) | 0.099 (4) | −0.012 (2) | 0.027 (3) | −0.006 (3) |
C212 | 0.080 (2) | 0.080 (5) | 0.082 (4) | −0.004 (3) | −0.015 (4) | −0.038 (3) |
C21 | 0.0448 (9) | 0.050 (2) | 0.0532 (12) | −0.0107 (12) | 0.0077 (9) | −0.0113 (16) |
C22 | 0.048 (2) | 0.0416 (11) | 0.0435 (12) | −0.0126 (11) | 0.0092 (14) | −0.0078 (8) |
O21 | 0.0461 (6) | 0.0387 (6) | 0.0399 (5) | −0.0045 (5) | 0.0090 (5) | −0.0042 (4) |
C11 | 0.0409 (7) | 0.0302 (7) | 0.0364 (7) | −0.0080 (6) | 0.0004 (6) | −0.0075 (6) |
O12 | 0.0616 (7) | 0.0322 (6) | 0.0510 (6) | −0.0049 (5) | 0.0082 (6) | 0.0000 (5) |
C12 | 0.0359 (7) | 0.0290 (7) | 0.0339 (7) | −0.0051 (6) | 0.0007 (6) | −0.0065 (5) |
O13 | 0.0348 (5) | 0.0349 (5) | 0.0388 (5) | −0.0034 (4) | −0.0026 (4) | −0.0105 (4) |
C14 | 0.0429 (8) | 0.0521 (10) | 0.0487 (9) | −0.0054 (7) | −0.0086 (7) | −0.0133 (7) |
C15 | 0.0421 (8) | 0.0545 (10) | 0.0431 (8) | −0.0085 (8) | −0.0046 (7) | −0.0029 (7) |
C16 | 0.0510 (11) | 0.0828 (15) | 0.0684 (13) | 0.0096 (10) | −0.0043 (10) | −0.0039 (11) |
C121 | 0.0382 (7) | 0.0324 (7) | 0.0353 (7) | −0.0126 (6) | 0.0000 (6) | −0.0021 (5) |
C122 | 0.0470 (8) | 0.0407 (8) | 0.0404 (8) | −0.0128 (7) | −0.0029 (7) | −0.0075 (6) |
C123 | 0.0671 (11) | 0.0556 (11) | 0.0463 (9) | −0.0224 (9) | −0.0085 (8) | −0.0102 (8) |
C124 | 0.0611 (11) | 0.0720 (13) | 0.0535 (10) | −0.0282 (10) | −0.0186 (9) | 0.0002 (9) |
C125 | 0.0436 (9) | 0.0635 (12) | 0.0617 (11) | −0.0107 (8) | −0.0124 (8) | 0.0069 (9) |
C126 | 0.0444 (8) | 0.0451 (9) | 0.0489 (9) | −0.0054 (7) | −0.0041 (7) | −0.0047 (7) |
C131 | 0.0365 (7) | 0.0306 (7) | 0.0389 (7) | −0.0065 (6) | −0.0001 (6) | −0.0060 (6) |
C132 | 0.0551 (9) | 0.0370 (8) | 0.0417 (8) | −0.0146 (7) | 0.0026 (7) | −0.0051 (6) |
C133 | 0.0647 (11) | 0.0384 (9) | 0.0575 (10) | −0.0171 (8) | 0.0051 (9) | 0.0012 (7) |
C134 | 0.0572 (10) | 0.0334 (8) | 0.0741 (12) | −0.0151 (8) | −0.0045 (9) | −0.0078 (8) |
C135 | 0.0547 (10) | 0.0379 (9) | 0.0589 (10) | −0.0094 (8) | −0.0123 (8) | −0.0148 (7) |
C136 | 0.0496 (9) | 0.0359 (8) | 0.0419 (8) | −0.0091 (7) | −0.0057 (7) | −0.0058 (6) |
C31 | 0.0410 (8) | 0.0420 (8) | 0.0398 (8) | −0.0002 (7) | −0.0074 (6) | −0.0044 (6) |
O31 | 0.0670 (8) | 0.0537 (7) | 0.0424 (6) | 0.0041 (6) | 0.0043 (6) | −0.0061 (5) |
C32 | 0.0416 (8) | 0.0405 (8) | 0.0443 (8) | −0.0074 (7) | −0.0084 (7) | 0.0011 (6) |
N32 | 0.0600 (9) | 0.0550 (9) | 0.0464 (8) | −0.0180 (8) | −0.0134 (7) | 0.0032 (6) |
O32 | 0.0622 (9) | 0.0881 (11) | 0.0710 (9) | −0.0208 (8) | 0.0053 (7) | 0.0144 (8) |
O33 | 0.0942 (10) | 0.0463 (7) | 0.0640 (8) | −0.0138 (7) | −0.0185 (7) | 0.0094 (6) |
C33 | 0.0454 (8) | 0.0371 (8) | 0.0520 (9) | −0.0041 (7) | −0.0133 (7) | −0.0073 (7) |
C34 | 0.0393 (8) | 0.0450 (9) | 0.0441 (8) | −0.0031 (7) | −0.0043 (7) | −0.0124 (7) |
N34 | 0.0474 (8) | 0.0617 (10) | 0.0562 (9) | −0.0045 (7) | −0.0035 (7) | −0.0219 (8) |
O34 | 0.0967 (12) | 0.0629 (9) | 0.0981 (12) | −0.0099 (8) | 0.0170 (9) | −0.0424 (8) |
O35 | 0.0716 (9) | 0.0897 (11) | 0.0557 (8) | −0.0140 (8) | 0.0126 (7) | −0.0159 (7) |
C35 | 0.0423 (8) | 0.0445 (9) | 0.0428 (8) | −0.0071 (7) | −0.0033 (7) | −0.0037 (6) |
C36 | 0.0465 (8) | 0.0358 (8) | 0.0451 (8) | −0.0061 (7) | −0.0056 (7) | −0.0057 (6) |
N36 | 0.0639 (9) | 0.0414 (8) | 0.0504 (8) | −0.0098 (7) | −0.0026 (7) | −0.0064 (6) |
O36 | 0.0896 (10) | 0.0533 (8) | 0.0851 (10) | −0.0293 (8) | 0.0079 (9) | −0.0052 (7) |
O37 | 0.0959 (11) | 0.0432 (7) | 0.0824 (10) | 0.0016 (7) | 0.0185 (8) | −0.0132 (7) |
N1—C111 | 1.492 (3) | C16—H16 | 0.9300 |
N1—C112 | 1.492 (4) | C121—C122 | 1.387 (2) |
N1—C1 | 1.495 (3) | C121—C126 | 1.390 (2) |
N1—H1 | 0.9800 | C122—C123 | 1.381 (2) |
C111—H11A | 0.9600 | C122—H122 | 0.9300 |
C111—H11B | 0.9600 | C123—C124 | 1.373 (3) |
C111—H11C | 0.9600 | C123—H123 | 0.9300 |
C112—H11D | 0.9600 | C124—C125 | 1.374 (3) |
C112—H11E | 0.9600 | C124—H124 | 0.9300 |
C112—H11F | 0.9600 | C125—C126 | 1.383 (2) |
C1—C2 | 1.503 (3) | C125—H125 | 0.9300 |
C1—H1A | 0.9700 | C126—H126 | 0.9300 |
C1—H1B | 0.9700 | C131—C132 | 1.386 (2) |
C2—O11 | 1.447 (3) | C131—C136 | 1.389 (2) |
C2—H2A | 0.9700 | C132—C133 | 1.376 (2) |
C2—H2B | 0.9700 | C132—H132 | 0.9300 |
O11—C11 | 1.3432 (16) | C133—C134 | 1.377 (3) |
N21—C211 | 1.489 (5) | C133—H133 | 0.9300 |
N21—C212 | 1.490 (5) | C134—C135 | 1.377 (3) |
N21—C21 | 1.493 (4) | C134—H134 | 0.9300 |
N21—H21 | 0.9800 | C135—C136 | 1.387 (2) |
C211—H21A | 0.9600 | C135—H135 | 0.9300 |
C211—H21B | 0.9600 | C136—H136 | 0.9300 |
C211—H21C | 0.9600 | C31—O31 | 1.2486 (17) |
C212—H21D | 0.9600 | C31—C36 | 1.439 (2) |
C212—H21E | 0.9600 | C31—C32 | 1.445 (2) |
C212—H21F | 0.9600 | C32—C33 | 1.367 (2) |
C21—C22 | 1.502 (4) | C32—N32 | 1.459 (2) |
C21—H21G | 0.9700 | N32—O32 | 1.220 (2) |
C21—H21H | 0.9700 | N32—O33 | 1.2267 (19) |
C22—H22A | 0.9700 | C33—C34 | 1.385 (2) |
C22—H22B | 0.9700 | C33—H33 | 0.9300 |
C11—O12 | 1.1925 (17) | C34—C35 | 1.379 (2) |
C11—C12 | 1.546 (2) | C34—N34 | 1.445 (2) |
C12—O13 | 1.4311 (15) | N34—O35 | 1.222 (2) |
C12—C121 | 1.529 (2) | N34—O34 | 1.223 (2) |
C12—C131 | 1.532 (2) | C35—C36 | 1.371 (2) |
O13—C14 | 1.4261 (19) | C35—H35 | 0.9300 |
C14—C15 | 1.447 (2) | C36—N36 | 1.453 (2) |
C14—H14A | 0.9700 | N36—O36 | 1.2170 (19) |
C14—H14B | 0.9700 | N36—O37 | 1.2226 (18) |
C15—C16 | 1.169 (2) | ||
C111—N1—C112 | 112.0 (3) | C15—C14—H14A | 109.6 |
C111—N1—C1 | 114.3 (3) | O13—C14—H14B | 109.6 |
C112—N1—C1 | 112.9 (3) | C15—C14—H14B | 109.6 |
C111—N1—H1 | 105.6 | H14A—C14—H14B | 108.1 |
C112—N1—H1 | 105.6 | C16—C15—C14 | 174.3 (2) |
C1—N1—H1 | 105.6 | C15—C16—H16 | 180.0 |
N1—C111—H11A | 109.5 | C122—C121—C126 | 118.53 (14) |
N1—C111—H11B | 109.5 | C122—C121—C12 | 121.32 (13) |
H11A—C111—H11B | 109.5 | C126—C121—C12 | 120.15 (13) |
N1—C111—H11C | 109.5 | C123—C122—C121 | 120.45 (15) |
H11A—C111—H11C | 109.5 | C123—C122—H122 | 119.8 |
H11B—C111—H11C | 109.5 | C121—C122—H122 | 119.8 |
N1—C112—H11D | 109.5 | C124—C123—C122 | 120.53 (16) |
N1—C112—H11E | 109.5 | C124—C123—H123 | 119.7 |
H11D—C112—H11E | 109.5 | C122—C123—H123 | 119.7 |
N1—C112—H11F | 109.5 | C123—C124—C125 | 119.72 (17) |
H11D—C112—H11F | 109.5 | C123—C124—H124 | 120.1 |
H11E—C112—H11F | 109.5 | C125—C124—H124 | 120.1 |
N1—C1—C2 | 116.3 (3) | C124—C125—C126 | 120.22 (17) |
N1—C1—H1A | 108.2 | C124—C125—H125 | 119.9 |
C2—C1—H1A | 108.2 | C126—C125—H125 | 119.9 |
N1—C1—H1B | 108.2 | C125—C126—C121 | 120.53 (15) |
C2—C1—H1B | 108.2 | C125—C126—H126 | 119.7 |
H1A—C1—H1B | 107.4 | C121—C126—H126 | 119.7 |
O11—C2—C1 | 108.8 (3) | C132—C131—C136 | 118.23 (14) |
O11—C2—H2A | 109.9 | C132—C131—C12 | 118.48 (13) |
C1—C2—H2A | 109.9 | C136—C131—C12 | 122.91 (13) |
O11—C2—H2B | 109.9 | C133—C132—C131 | 121.04 (15) |
C1—C2—H2B | 109.9 | C133—C132—H132 | 119.5 |
H2A—C2—H2B | 108.3 | C131—C132—H132 | 119.5 |
C11—O11—C2 | 113.4 (3) | C132—C133—C134 | 120.36 (16) |
C211—N21—C212 | 111.9 (6) | C132—C133—H133 | 119.8 |
C211—N21—C21 | 114.3 (6) | C134—C133—H133 | 119.8 |
C212—N21—C21 | 113.7 (5) | C133—C134—C135 | 119.54 (16) |
C211—N21—H21 | 105.3 | C133—C134—H134 | 120.2 |
C212—N21—H21 | 105.3 | C135—C134—H134 | 120.2 |
C21—N21—H21 | 105.3 | C134—C135—C136 | 120.19 (16) |
N21—C211—H21A | 109.5 | C134—C135—H135 | 119.9 |
N21—C211—H21B | 109.5 | C136—C135—H135 | 119.9 |
H21A—C211—H21B | 109.5 | C135—C136—C131 | 120.62 (15) |
N21—C211—H21C | 109.5 | C135—C136—H136 | 119.7 |
H21A—C211—H21C | 109.5 | C131—C136—H136 | 119.7 |
H21B—C211—H21C | 109.5 | O31—C31—C36 | 124.73 (15) |
N21—C212—H21D | 109.5 | O31—C31—C32 | 123.31 (15) |
N21—C212—H21E | 109.5 | C36—C31—C32 | 111.87 (13) |
H21D—C212—H21E | 109.5 | C33—C32—C31 | 124.78 (15) |
N21—C212—H21F | 109.5 | C33—C32—N32 | 117.05 (14) |
H21D—C212—H21F | 109.5 | C31—C32—N32 | 118.17 (14) |
H21E—C212—H21F | 109.5 | O32—N32—O33 | 123.34 (16) |
N21—C21—C22 | 116.8 (6) | O32—N32—C32 | 118.84 (15) |
N21—C21—H21G | 108.1 | O33—N32—C32 | 117.82 (15) |
C22—C21—H21G | 108.1 | C32—C33—C34 | 118.50 (15) |
N21—C21—H21H | 108.1 | C32—C33—H33 | 120.8 |
C22—C21—H21H | 108.1 | C34—C33—H33 | 120.8 |
H21G—C21—H21H | 107.3 | C35—C34—C33 | 121.46 (14) |
C21—C22—H22A | 109.9 | C35—C34—N34 | 118.57 (15) |
C21—C22—H22B | 109.9 | C33—C34—N34 | 119.97 (15) |
H22A—C22—H22B | 108.3 | O35—N34—O34 | 123.21 (15) |
O12—C11—O11 | 123.37 (13) | O35—N34—C34 | 118.67 (15) |
O12—C11—C12 | 124.45 (13) | O34—N34—C34 | 118.12 (17) |
O11—C11—C12 | 112.07 (11) | C36—C35—C34 | 119.12 (15) |
O13—C12—C121 | 106.58 (10) | C36—C35—H35 | 120.4 |
O13—C12—C131 | 109.47 (11) | C34—C35—H35 | 120.4 |
C121—C12—C131 | 111.76 (11) | C35—C36—C31 | 124.26 (14) |
O13—C12—C11 | 108.04 (11) | C35—C36—N36 | 116.46 (15) |
C121—C12—C11 | 105.98 (11) | C31—C36—N36 | 119.27 (13) |
C131—C12—C11 | 114.62 (11) | O36—N36—O37 | 122.06 (15) |
C14—O13—C12 | 114.74 (10) | O36—N36—C36 | 118.51 (14) |
O13—C14—C15 | 110.22 (13) | O37—N36—C36 | 119.38 (15) |
O13—C14—H14A | 109.6 | ||
C111—N1—C1—C2 | −75.6 (5) | C11—C12—C131—C136 | −25.2 (2) |
C112—N1—C1—C2 | 54.0 (6) | C136—C131—C132—C133 | 0.0 (2) |
N1—C1—C2—O11 | 67.3 (7) | C12—C131—C132—C133 | 173.15 (15) |
C1—C2—O11—C11 | 172.8 (4) | C131—C132—C133—C134 | 0.5 (3) |
C211—N21—C21—C22 | −77.1 (10) | C132—C133—C134—C135 | 0.1 (3) |
C212—N21—C21—C22 | 53.1 (12) | C133—C134—C135—C136 | −1.0 (3) |
C2—O11—C11—O12 | 2.3 (5) | C134—C135—C136—C131 | 1.4 (3) |
C2—O11—C11—C12 | −174.0 (5) | C132—C131—C136—C135 | −0.9 (2) |
O12—C11—C12—O13 | 13.1 (2) | C12—C131—C136—C135 | −173.77 (14) |
O11—C11—C12—O13 | −170.68 (11) | O31—C31—C32—C33 | −176.05 (16) |
O12—C11—C12—C121 | −100.86 (17) | C36—C31—C32—C33 | 0.6 (2) |
O11—C11—C12—C121 | 75.41 (14) | O31—C31—C32—N32 | 4.9 (2) |
O12—C11—C12—C131 | 135.39 (16) | C36—C31—C32—N32 | −178.42 (13) |
O11—C11—C12—C131 | −48.34 (17) | C33—C32—N32—O32 | −142.86 (17) |
C121—C12—O13—C14 | −174.95 (12) | C31—C32—N32—O32 | 36.3 (2) |
C131—C12—O13—C14 | −53.92 (15) | C33—C32—N32—O33 | 36.5 (2) |
C11—C12—O13—C14 | 71.53 (15) | C31—C32—N32—O33 | −144.32 (16) |
C12—O13—C14—C15 | −171.72 (13) | C31—C32—C33—C34 | −0.7 (2) |
O13—C12—C121—C122 | −7.05 (18) | N32—C32—C33—C34 | 178.39 (14) |
C131—C12—C121—C122 | −126.61 (14) | C32—C33—C34—C35 | 0.8 (2) |
C11—C12—C121—C122 | 107.87 (15) | C32—C33—C34—N34 | −179.70 (14) |
O13—C12—C121—C126 | 173.18 (13) | C35—C34—N34—O35 | 0.1 (2) |
C131—C12—C121—C126 | 53.63 (17) | C33—C34—N34—O35 | −179.37 (15) |
C11—C12—C121—C126 | −71.90 (16) | C35—C34—N34—O34 | 179.07 (16) |
C126—C121—C122—C123 | −0.5 (2) | C33—C34—N34—O34 | −0.4 (2) |
C12—C121—C122—C123 | 179.77 (14) | C33—C34—C35—C36 | −0.9 (2) |
C121—C122—C123—C124 | 0.9 (3) | N34—C34—C35—C36 | 179.57 (15) |
C122—C123—C124—C125 | −0.4 (3) | C34—C35—C36—C31 | 0.9 (2) |
C123—C124—C125—C126 | −0.6 (3) | C34—C35—C36—N36 | −178.34 (14) |
C124—C125—C126—C121 | 1.0 (3) | O31—C31—C36—C35 | 175.86 (16) |
C122—C121—C126—C125 | −0.4 (2) | C32—C31—C36—C35 | −0.8 (2) |
C12—C121—C126—C125 | 179.32 (15) | O31—C31—C36—N36 | −4.9 (2) |
O13—C12—C131—C132 | −76.50 (16) | C32—C31—C36—N36 | 178.50 (14) |
C121—C12—C131—C132 | 41.34 (17) | C35—C36—N36—O36 | −25.2 (2) |
C11—C12—C131—C132 | 161.95 (13) | C31—C36—N36—O36 | 155.44 (16) |
O13—C12—C131—C136 | 96.35 (16) | C35—C36—N36—O37 | 152.17 (16) |
C121—C12—C131—C136 | −145.81 (14) | C31—C36—N36—O37 | −27.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O31 | 0.98 | 1.72 | 2.633 (7) | 153 |
N1—H1···O37 | 0.98 | 2.33 | 3.010 (7) | 126 |
N21—H21···O31 | 0.98 | 1.77 | 2.697 (14) | 157 |
N21—H21···O37 | 0.98 | 2.34 | 2.944 (14) | 120 |
C2—H2B···O33i | 0.97 | 2.56 | 3.338 (9) | 137 |
C14—H14B···O32i | 0.97 | 2.52 | 3.407 (2) | 153 |
C135—H135···O31ii | 0.93 | 2.58 | 3.485 (2) | 165 |
Symmetry codes: (i) x−1, y+1, z; (ii) x−1, y, z. |
Acknowledgements
The authors thank the DST–PURSE Lab (Mangalore University) for the diffractometer and other facilities. MAES thanks the University of Mysore for research facilities.
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