research communications
Syntheses and crystal structures of 4-(4-methoxyphenyl)piperazin-1-ium 4-methylbenzoate monohydrate and bis[4-(4-methoxyphenyl)piperazin-1-ium] benzene-1,2-dicarboxylate
aDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore-570 005, India, bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570 006, India, cDepartment of Chemistry, University of Kentucky, Lexington, KY 40506, USA, and dSchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UK
*Correspondence e-mail: yathirajan@hotmail.com
Co-crystallization of N-(4-methoxyphenyl)piperazine with 4-methylbenzoic acid and with benzene-1,2-dicarboxylic acid yields the salts 4-(4-methoxyphenyl)piperazin-1-ium 4-methylbenzoate monohydrate, C11H17N2O+·C8H7O2−·H2O (I), and bis[4-(4-methoxyphenyl)piperazin-1-ium] benzene-1,2-dicarboxylate, 2C11H17N2O+·C8H4O42− (II). These salts both crystallize with Z′ = 2, in space groups P and Pna21, respectively. In compound (I), a combination of four O—H⋯O, four N—H⋯O, one C—H⋯O and one C—H⋯π(arene) hydrogen bonds link the six independent components into complex sheets, within which the two piperazine rings, the two anions, and the two water molecules are related by an approximate, non-crystallographic translation along the b-axis direction. In compound (II), sheets containing R44(18) and R1012(38) rings are formed by the combined action of eight independent N—H⋯O hydrogen bonds. Comparisons are made with the structures of some related compounds.
1. Chemical context
Piperazine derivatives can exhibit a very wide range of biological activity (Asif, 2015; Brito et al., 2019). In addition, N-(4-methoxyphenyl)piperazine (MeOPP) is a recreational drug whose action on human physiology resembles that of amphetamines, but which appears to have significantly lower potential for abuse (Nagai et al., 2007). With these considerations in mind, we have recently initiated a structural study of MeOPP and its derivatives (Kiran Kumar, Yathirajan, Foro et al., 2019; Kiran Kumar, Yathirajan, Sagar et al., 2019; Kiran Kumar et al., 2020): this has included the structures of a number of salts derived from simple aromatic acids (Kiran Kumar, Yathirajan, Foro et al., 2019; Kiran Kumar et al., 2020). In a continuation of these earlier studies, we now report the structures of two further salts, namely 4-(4-methoxyphenyl)piperazin-1-ium 4-methylbenzoate monohydrate (I) and bis[4-(4-methoxyphenyl)piperazin-1-ium] benzene-1,2-dicarboxylate (II) (see scheme and Figs. 1–3).
2. Structural commentary
Co-crystallization of N-(4-methoxyphenyl)piperazine and 4-methylbenzoic acid yielded a 1:1 salt, which crystallized from methanol–ethyl acetate in air as a monohydrate, with Z′ = 2 in P (Fig. 1). A search for possible additional symmetry revealed none. The possibility of any such symmetry is effectively precluded by the different orientations of the 4-methoxyphenyl unit relative to the piperazine ring in the two independent cations, as indicated by the values of the torsion angles Cx3—Nx4—Cx41—Cx42 (x = 1 or 2, Fig. 1), −5.45 (18)° when x = 1, but −46.92 (17)° when x = 2. Apart from this difference, the other pairs of corresponding units (the two piperazine rings, the two anions, and the two water molecules) are related by an approximate, non-crystallographic translation (x, 0.5 + y, z). Although there are six independent components in the structure, it is possible to select a compact in which the components are linked by three O—H⋯O hydrogen bonds and two N—H⋯O hydrogen bonds (Fig. 1, Table 1).
Compound (II), formed by co-crystallization of N-(4-methoxyphenyl)piperazine with benzene-1,2-dicarboxylic acid (phthalic acid), is a 2:1 salt that crystallizes in solvent-free form with Z′ = 2 in Pna21. A search for possible additional symmetry revealed none. As for compound (I), there are six independent components in the structure of (II), four cations and two anions, providing a considerable degree of choice in the specification of the The selection here consists of two similar ion triplets, each comprising two cations and one anion, which are linked in each triplet by two N—H⋯O hydrogen bonds (Figs. 2 and 3). It will be convenient to refer to the ion triplet containing atom N11 (Fig. 2) as of type 1, and that containing atom N21 (Fig. 3) as of type 2.
In the cations of compound (I), the methoxy C atoms are close to the plane of the adjacent rings, with displacements from these planes of 0.118 (3) and 0.073 (4) Å for atoms C147 and C247, respectively. In compound (II), the corresponding displacements are 0.242 (6), 0.070 (6) and 0.097 (6) Å for atoms C147, C247 and C447, respectively, but 0.750 (6) Å for atom C347. At the same time, the pairs of exocyclic O—C—C angles at C144 and C244 in (I), and at C144, C244 and C444 in (II) all differ by ca 10°. This behaviour is characteristic of planar and near-planar alkoxyarenes (Seip & Seip, 1973; Ferguson et al., 1996; Kiran Kumar et al., 2020). On the other hand, the difference between the exocyclic angles at atom C344 in (II) is only 6.7 (5)°.
3. Supramolecular features
The supramolecular assembly of compound (I) is di-periodic (propagates in two-dimensions) and is built from a combination of O—H⋯O, N—H⋯O, C—H⋯O and C—H⋯π(arene) hydrogen bonds (Table 1). However, the assembly can readily be analysed in terms of a number of simple substructures (Ferguson et al., 1998a,b; Gregson et al., 2000). The two independent anions and the two independent water molecules are linked by O—H⋯O hydrogen bonds to form a C44(12) (Etter, 1990; Etter et al., 1990; Bernstein et al., 1995) chain running parallel to the [010] direction (Fig. 4). Inversion-related pairs of chains of this type are linked by the two types of cation to form a molecular ribbon in the form of a chain of edge-fused R87(20) rings parallel to [010] along the line (1, y, 0.5) (Fig. 5). The ribbons along [010] are linked into sheets lying parallel to (001) by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds, and it is convenient to consider separately the sub-structures formed by these two types of interaction. In the simpler of these two sub-structures, (Fig. 6), inversion-related ion pairs are linked by C—H⋯O hydrogen bonds (Table 1) to form an R42(10) ring, which links the chains along (1, y, 0.5) and (0, y, 0.5). The second sub-structure (Fig. 7) contains C—H⋯π(arene) hydrogen bonds and also includes water molecules but, again, it links the chains along (1, y, 0.5) and (0, y, 0.5). Propagation of these motifs by inversion thus links adjacent [010] chains into a complex sheet lying parallel to (001).
There are eight independent N—H⋯O hydrogen bonds in the structure of compound (II) (Table 2). Four of these lie within the two ion triplets that were selected as the (Figs. 2 and 3), and the other four act to link the type 1 and type 2 triplets into sheets of alternating R44(18) and R1210(38) rings lying parallel to (001) (Fig. 8). Two sheets of this type, which are related to one another by the action of the 21 screw axis, pass through each in the domains 0.25 < z < 0.75 and 0.75 < z < 1.25, but there are no direction-specific interactions between adjacent sheets: the C—H⋯O and C—H⋯π(arene) hydrogen bonds all lie within a single sheet.
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4. Database survey
In addition to the structures of a number of salts formed between N-(4-methoxyphenyl)piperazine and carboxylic acids (Kiran Kumar, Yathirajan, Foro et al., 2019; Kiran Kumar, Yathirajan, Sagar et al., 2019), structures have also been reported for the chloride (Zia-ur-Rehman et al., 2009) and tetra(isothiocyanato)cobaltate(II) salts (Gharbi et al., 2021). By contrast, the only structures reported for salts of the isomeric N-(3-methoxyphenyl)piperazine are those of the maleate (Verdonk et al., 1997) and the 4-(3-methoxyphenyl)piperazin-1-carboxylate (Özdemir, 2021). In addition to the structures reported for the picrate (Verdonk et al., 1997) and 6-chloro-5-isopropyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ide (Al-Omary et al., 2014) salts derived from N-(2-methoxyphenyl)piperazine, we have recently reported (Harish Chinthal et al., 2020) the structures of fifteen salts formed by this piperazine with organic acids, where it was found that the supramolecular assemblies range from finite (non-periodic) aggregates through mono-, di- and tri-periodic arrangements.
5. Synthesis and crystallization
For the preparation of compounds (I) and (II), a solution of N-(4-methoxypiperazine (100 mg, 0.52 mmol) in methanol (10 ml) was mixed with a solution of the appropriate acid, 4-methylbenzoic acid (76 mg, 0.52 mmol) for (I), or benzene-1,2-dicarboxylic acid (phthalic acid, 86 mg, 0.52 mmol) for (II), each in methanol (10 ml). The mixtures were stirred briefly and then set aside at ambient temperature, giving colourless crystals of compounds (I) and (II) after a few days: compound (I), yield 80%, m.p. 413–416 K, compound (II), yield 80%, m.p. 446–447 K. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation, at ambient temperature and in the presence of air, of solutions in methanol–ethyl acetate (initial composition 1:1, v/v).
6. Data collection and structure refinement
Crystals of (I) shattered on cooling to 90 K, while those of compound (II) showed faint satellite reflections at 90 K that gradually diminished in intensity on warming. At the data collection temperature of 180–K, crystals of (I) remained intact and the satellite reflections observed for (II) were absent. Crystal data, data collection and details are summarized in Table 3. All H atoms were located in difference maps. The H atoms bonded to C atoms were then treated as riding atoms in geometrically idealised positions with C—H distances 0.95 Å (aromatic), 0.98 Å (CH3 or 0.99 Å (CH2), and with Uiso(H) = kUeq(C), 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 bonded to C atoms. For the H atoms bonded to N or O atoms, the atomic coordinates were refined with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(O), giving the N—H and O—H distances shown in Tables 1 and 2. For compound (II), Cu Kα radiation was used to facilitate establishing a unique orientation for the structure with respect to the polar axis direction. For the crystal selected for data collection, however, the value of the Flack x parameter (Flack, 1983), obtained in the conventional way via full-matrix least-squares i.e. x = 0.45 (18) was inconclusive due to its high while that calculated using 4511 quotients (Parsons et al., 2013) of the type [(I+) − (I−)]/[(I+) + (I−)] was x = 0.45 (5), strongly suggesting the likelihood of by inversion.
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Supporting information
https://doi.org/10.1107/S2056989022008337/zl5034sup1.cif
contains datablocks global, I, II. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022008337/zl5034Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989022008337/zl5034IIsup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989022008337/zl5034Isup4.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989022008337/zl5034IIsup5.cml
For both structures, data collection: APEX3 (Bruker, 2016); cell
APEX3 (Bruker, 2016); data reduction: APEX3 (Bruker, 2016); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020).C11H17N2O+·C8H7O2−·H2O | Z = 4 |
Mr = 346.42 | F(000) = 744 |
Triclinic, P1 | Dx = 1.277 Mg m−3 |
a = 7.4141 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.3595 (11) Å | Cell parameters from 8258 reflections |
c = 19.9917 (17) Å | θ = 1.9–27.5° |
α = 86.695 (2)° | µ = 0.09 mm−1 |
β = 83.654 (2)° | T = 180 K |
γ = 82.182 (3)° | Needle, colourless |
V = 1802.1 (3) Å3 | 0.30 × 0.18 × 0.08 mm |
Bruker D8 Venture dual source diffractometer | 8288 independent reflections |
Radiation source: microsource | 5772 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.050 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −9→8 |
Tmin = 0.938, Tmax = 0.971 | k = −16→16 |
54020 measured reflections | l = −25→25 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0586P)2 + 0.3838P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
8288 reflections | Δρmax = 0.30 e Å−3 |
479 parameters | Δρmin = −0.18 e Å−3 |
0 restraints |
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 | ||
N11 | 0.76096 (16) | 0.62068 (10) | 0.54566 (6) | 0.0267 (3) | |
H11 | 0.733 (2) | 0.6044 (12) | 0.5026 (8) | 0.032* | |
H12 | 0.880 (2) | 0.6350 (12) | 0.5392 (7) | 0.032* | |
C12 | 0.7518 (2) | 0.52384 (11) | 0.59281 (7) | 0.0310 (3) | |
H12A | 0.8359 | 0.4610 | 0.5742 | 0.037* | |
H12B | 0.6260 | 0.5039 | 0.5981 | 0.037* | |
C13 | 0.8047 (2) | 0.54855 (11) | 0.66075 (7) | 0.0294 (3) | |
H13A | 0.7922 | 0.4845 | 0.6922 | 0.035* | |
H13B | 0.9346 | 0.5612 | 0.6559 | 0.035* | |
N14 | 0.69096 (14) | 0.64449 (9) | 0.68905 (5) | 0.0240 (2) | |
C15 | 0.69514 (18) | 0.74004 (10) | 0.64205 (6) | 0.0255 (3) | |
H15A | 0.8203 | 0.7610 | 0.6359 | 0.031* | |
H15B | 0.6112 | 0.8024 | 0.6614 | 0.031* | |
C16 | 0.63897 (18) | 0.71658 (11) | 0.57442 (6) | 0.0280 (3) | |
H16A | 0.5105 | 0.7011 | 0.5798 | 0.034* | |
H16B | 0.6472 | 0.7814 | 0.5433 | 0.034* | |
C141 | 0.71549 (17) | 0.66404 (11) | 0.75664 (6) | 0.0243 (3) | |
C142 | 0.8279 (2) | 0.59160 (12) | 0.79520 (7) | 0.0355 (3) | |
H142 | 0.8979 | 0.5294 | 0.7751 | 0.043* | |
C143 | 0.8388 (2) | 0.60898 (14) | 0.86214 (7) | 0.0426 (4) | |
H143 | 0.9144 | 0.5578 | 0.8876 | 0.051* | |
C144 | 0.7416 (2) | 0.69941 (13) | 0.89278 (7) | 0.0369 (3) | |
C145 | 0.6318 (2) | 0.77281 (12) | 0.85531 (7) | 0.0348 (3) | |
H145 | 0.5649 | 0.8358 | 0.8755 | 0.042* | |
C146 | 0.61891 (19) | 0.75492 (12) | 0.78825 (7) | 0.0299 (3) | |
H146 | 0.5421 | 0.8061 | 0.7632 | 0.036* | |
O144 | 0.76486 (19) | 0.70874 (10) | 0.95950 (5) | 0.0570 (4) | |
C147 | 0.6805 (3) | 0.80445 (16) | 0.99074 (8) | 0.0634 (6) | |
H17A | 0.7279 | 0.8681 | 0.9672 | 0.095* | |
H17B | 0.7069 | 0.8009 | 1.0378 | 0.095* | |
H17C | 0.5479 | 0.8111 | 0.9889 | 0.095* | |
N21 | 0.75064 (16) | 0.11429 (10) | 0.54577 (6) | 0.0264 (2) | |
H21 | 0.723 (2) | 0.0975 (12) | 0.5026 (8) | 0.032* | |
H22 | 0.867 (2) | 0.1300 (12) | 0.5412 (7) | 0.032* | |
C22 | 0.7444 (2) | 0.01754 (11) | 0.59339 (7) | 0.0299 (3) | |
H22A | 0.8321 | −0.0443 | 0.5755 | 0.036* | |
H22B | 0.6202 | −0.0048 | 0.5982 | 0.036* | |
C23 | 0.79276 (19) | 0.04501 (11) | 0.66152 (7) | 0.0291 (3) | |
H23A | 0.7829 | −0.0189 | 0.6933 | 0.035* | |
H23B | 0.9212 | 0.0604 | 0.6571 | 0.035* | |
N24 | 0.67239 (14) | 0.14015 (9) | 0.68904 (5) | 0.0239 (2) | |
C25 | 0.67558 (18) | 0.23465 (11) | 0.64143 (6) | 0.0257 (3) | |
H25A | 0.7999 | 0.2569 | 0.6356 | 0.031* | |
H25B | 0.5892 | 0.2967 | 0.6599 | 0.031* | |
C26 | 0.62318 (18) | 0.20845 (11) | 0.57381 (6) | 0.0274 (3) | |
H26A | 0.4963 | 0.1903 | 0.5790 | 0.033* | |
H26B | 0.6283 | 0.2731 | 0.5424 | 0.033* | |
C241 | 0.70163 (17) | 0.16099 (11) | 0.75612 (6) | 0.0249 (3) | |
C242 | 0.7146 (2) | 0.07628 (13) | 0.80489 (7) | 0.0428 (4) | |
H242 | 0.7053 | 0.0041 | 0.7929 | 0.051* | |
C243 | 0.7406 (3) | 0.09470 (14) | 0.87012 (8) | 0.0518 (5) | |
H243 | 0.7485 | 0.0352 | 0.9024 | 0.062* | |
C244 | 0.7554 (2) | 0.19800 (14) | 0.88941 (7) | 0.0391 (4) | |
C245 | 0.7391 (2) | 0.28321 (14) | 0.84304 (8) | 0.0441 (4) | |
H245 | 0.7458 | 0.3553 | 0.8557 | 0.053* | |
C246 | 0.7126 (2) | 0.26424 (13) | 0.77696 (7) | 0.0402 (4) | |
H246 | 0.7018 | 0.3244 | 0.7452 | 0.048* | |
O244 | 0.7874 (2) | 0.20623 (11) | 0.95543 (6) | 0.0610 (4) | |
C247 | 0.8036 (3) | 0.31074 (18) | 0.97722 (10) | 0.0723 (7) | |
H27A | 0.9015 | 0.3418 | 0.9486 | 0.109* | |
H27B | 0.8328 | 0.3045 | 1.0240 | 0.109* | |
H27C | 0.6877 | 0.3586 | 0.9742 | 0.109* | |
C31 | 0.75414 (17) | 0.59237 (11) | 0.30344 (7) | 0.0263 (3) | |
C32 | 0.8027 (2) | 0.66491 (12) | 0.25084 (7) | 0.0354 (3) | |
H32 | 0.8517 | 0.7290 | 0.2600 | 0.042* | |
C33 | 0.7799 (2) | 0.64400 (14) | 0.18531 (8) | 0.0437 (4) | |
H33 | 0.8126 | 0.6946 | 0.1499 | 0.052* | |
C34 | 0.7104 (2) | 0.55090 (14) | 0.17012 (8) | 0.0399 (4) | |
C35 | 0.6671 (2) | 0.47747 (13) | 0.22262 (7) | 0.0375 (4) | |
H35 | 0.6231 | 0.4119 | 0.2132 | 0.045* | |
C36 | 0.68710 (18) | 0.49820 (12) | 0.28865 (7) | 0.0308 (3) | |
H36 | 0.6546 | 0.4475 | 0.3240 | 0.037* | |
C37 | 0.77205 (18) | 0.61793 (11) | 0.37504 (7) | 0.0289 (3) | |
O31 | 0.69445 (14) | 0.56144 (8) | 0.42179 (5) | 0.0355 (2) | |
O32 | 0.86049 (16) | 0.69333 (10) | 0.38415 (6) | 0.0465 (3) | |
C38 | 0.6821 (3) | 0.52858 (18) | 0.09872 (9) | 0.0619 (5) | |
H38A | 0.6373 | 0.5972 | 0.0753 | 0.093* | |
H38B | 0.5922 | 0.4772 | 0.0995 | 0.093* | |
H38C | 0.7986 | 0.4969 | 0.0751 | 0.093* | |
C41 | 0.78088 (17) | 0.09275 (11) | 0.30254 (7) | 0.0257 (3) | |
C42 | 0.85635 (19) | 0.16165 (12) | 0.25294 (8) | 0.0348 (3) | |
H42 | 0.9018 | 0.2252 | 0.2652 | 0.042* | |
C43 | 0.8655 (2) | 0.13794 (14) | 0.18548 (8) | 0.0433 (4) | |
H43 | 0.9165 | 0.1860 | 0.1520 | 0.052* | |
C44 | 0.8020 (2) | 0.04568 (14) | 0.16608 (7) | 0.0409 (4) | |
C45 | 0.7276 (2) | −0.02308 (13) | 0.21581 (7) | 0.0363 (3) | |
H45 | 0.6831 | −0.0868 | 0.2034 | 0.044* | |
C46 | 0.71718 (18) | −0.00019 (11) | 0.28337 (7) | 0.0290 (3) | |
H46 | 0.6661 | −0.0484 | 0.3167 | 0.035* | |
C47 | 0.77169 (18) | 0.11822 (12) | 0.37561 (7) | 0.0297 (3) | |
O41 | 0.69295 (14) | 0.05664 (9) | 0.41930 (5) | 0.0358 (2) | |
O42 | 0.84243 (17) | 0.19826 (10) | 0.38947 (6) | 0.0529 (3) | |
C48 | 0.8102 (3) | 0.01966 (18) | 0.09276 (8) | 0.0642 (6) | |
H48A | 0.8524 | 0.0805 | 0.0644 | 0.096* | |
H48B | 0.6880 | 0.0087 | 0.0823 | 0.096* | |
H48C | 0.8954 | −0.0471 | 0.0840 | 0.096* | |
O51 | 0.87815 (14) | 0.85863 (9) | 0.46119 (5) | 0.0333 (2) | |
H51 | 0.813 (3) | 0.9175 (16) | 0.4445 (9) | 0.050* | |
H52 | 0.864 (2) | 0.8028 (15) | 0.4347 (9) | 0.050* | |
O61 | 0.86471 (14) | 0.36156 (9) | 0.46571 (5) | 0.0340 (2) | |
H61 | 0.845 (2) | 0.3057 (16) | 0.4412 (9) | 0.051* | |
H62 | 0.797 (3) | 0.4234 (16) | 0.4492 (9) | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0281 (6) | 0.0315 (7) | 0.0209 (6) | −0.0048 (5) | −0.0022 (4) | −0.0048 (5) |
C12 | 0.0388 (8) | 0.0254 (7) | 0.0290 (7) | −0.0034 (6) | −0.0017 (6) | −0.0065 (6) |
C13 | 0.0397 (8) | 0.0217 (7) | 0.0254 (7) | 0.0019 (6) | −0.0039 (6) | −0.0014 (5) |
N14 | 0.0294 (6) | 0.0214 (6) | 0.0205 (5) | −0.0016 (4) | −0.0019 (4) | −0.0019 (4) |
C15 | 0.0307 (7) | 0.0219 (7) | 0.0230 (6) | −0.0013 (5) | −0.0019 (5) | −0.0004 (5) |
C16 | 0.0310 (7) | 0.0281 (7) | 0.0239 (7) | 0.0009 (5) | −0.0034 (5) | −0.0023 (5) |
C141 | 0.0263 (6) | 0.0253 (7) | 0.0217 (6) | −0.0048 (5) | −0.0027 (5) | 0.0000 (5) |
C142 | 0.0426 (8) | 0.0326 (8) | 0.0292 (7) | 0.0058 (6) | −0.0071 (6) | −0.0023 (6) |
C143 | 0.0540 (10) | 0.0418 (9) | 0.0303 (8) | 0.0071 (7) | −0.0144 (7) | 0.0008 (7) |
C144 | 0.0487 (9) | 0.0404 (9) | 0.0228 (7) | −0.0058 (7) | −0.0085 (6) | −0.0030 (6) |
C145 | 0.0422 (8) | 0.0335 (8) | 0.0278 (7) | 0.0012 (6) | −0.0041 (6) | −0.0074 (6) |
C146 | 0.0340 (7) | 0.0308 (8) | 0.0244 (7) | 0.0021 (6) | −0.0070 (5) | −0.0024 (6) |
O144 | 0.0881 (10) | 0.0560 (8) | 0.0260 (6) | 0.0075 (7) | −0.0207 (6) | −0.0079 (5) |
C147 | 0.1103 (17) | 0.0533 (12) | 0.0268 (9) | −0.0018 (11) | −0.0142 (9) | −0.0118 (8) |
N21 | 0.0262 (6) | 0.0316 (7) | 0.0220 (6) | −0.0038 (5) | −0.0028 (4) | −0.0047 (5) |
C22 | 0.0371 (7) | 0.0245 (7) | 0.0286 (7) | −0.0034 (6) | −0.0038 (6) | −0.0056 (6) |
C23 | 0.0362 (7) | 0.0241 (7) | 0.0259 (7) | 0.0017 (6) | −0.0045 (5) | −0.0018 (5) |
N24 | 0.0274 (6) | 0.0227 (6) | 0.0213 (5) | −0.0019 (4) | −0.0034 (4) | −0.0015 (4) |
C25 | 0.0276 (7) | 0.0228 (7) | 0.0255 (7) | 0.0001 (5) | −0.0018 (5) | −0.0012 (5) |
C26 | 0.0283 (7) | 0.0295 (7) | 0.0234 (7) | 0.0007 (5) | −0.0039 (5) | −0.0005 (5) |
C241 | 0.0238 (6) | 0.0274 (7) | 0.0236 (6) | −0.0035 (5) | −0.0021 (5) | −0.0022 (5) |
C242 | 0.0697 (11) | 0.0306 (8) | 0.0307 (8) | −0.0103 (8) | −0.0128 (7) | 0.0008 (6) |
C243 | 0.0867 (14) | 0.0402 (10) | 0.0300 (8) | −0.0060 (9) | −0.0191 (8) | 0.0056 (7) |
C244 | 0.0463 (9) | 0.0474 (10) | 0.0239 (7) | −0.0008 (7) | −0.0087 (6) | −0.0063 (7) |
C245 | 0.0665 (11) | 0.0359 (9) | 0.0320 (8) | −0.0076 (8) | −0.0092 (7) | −0.0095 (7) |
C246 | 0.0646 (11) | 0.0289 (8) | 0.0281 (7) | −0.0080 (7) | −0.0068 (7) | −0.0008 (6) |
O244 | 0.0957 (10) | 0.0601 (8) | 0.0294 (6) | 0.0005 (7) | −0.0246 (6) | −0.0107 (6) |
C247 | 0.1032 (18) | 0.0722 (15) | 0.0462 (11) | 0.0022 (12) | −0.0323 (11) | −0.0265 (10) |
C31 | 0.0226 (6) | 0.0281 (7) | 0.0281 (7) | 0.0011 (5) | −0.0045 (5) | −0.0063 (6) |
C32 | 0.0431 (8) | 0.0276 (8) | 0.0362 (8) | −0.0041 (6) | −0.0080 (6) | −0.0014 (6) |
C33 | 0.0572 (10) | 0.0415 (10) | 0.0323 (8) | −0.0056 (8) | −0.0089 (7) | 0.0047 (7) |
C34 | 0.0397 (8) | 0.0495 (10) | 0.0304 (8) | −0.0005 (7) | −0.0072 (6) | −0.0083 (7) |
C35 | 0.0356 (8) | 0.0440 (9) | 0.0359 (8) | −0.0108 (7) | −0.0032 (6) | −0.0160 (7) |
C36 | 0.0291 (7) | 0.0332 (8) | 0.0306 (7) | −0.0068 (6) | 0.0004 (5) | −0.0062 (6) |
C37 | 0.0262 (7) | 0.0286 (7) | 0.0314 (7) | 0.0050 (6) | −0.0075 (5) | −0.0097 (6) |
O31 | 0.0410 (6) | 0.0402 (6) | 0.0255 (5) | −0.0021 (5) | −0.0049 (4) | −0.0069 (4) |
O32 | 0.0521 (7) | 0.0477 (7) | 0.0452 (7) | −0.0166 (5) | −0.0084 (5) | −0.0191 (5) |
C38 | 0.0717 (13) | 0.0817 (15) | 0.0349 (9) | −0.0065 (11) | −0.0154 (9) | −0.0130 (9) |
C41 | 0.0228 (6) | 0.0271 (7) | 0.0277 (7) | −0.0004 (5) | −0.0065 (5) | −0.0046 (5) |
C42 | 0.0324 (7) | 0.0299 (8) | 0.0433 (9) | −0.0060 (6) | −0.0060 (6) | −0.0012 (6) |
C43 | 0.0465 (9) | 0.0445 (10) | 0.0359 (8) | −0.0040 (7) | 0.0017 (7) | 0.0074 (7) |
C44 | 0.0474 (9) | 0.0446 (9) | 0.0282 (8) | 0.0061 (7) | −0.0055 (6) | −0.0039 (7) |
C45 | 0.0446 (9) | 0.0319 (8) | 0.0336 (8) | −0.0004 (6) | −0.0119 (6) | −0.0094 (6) |
C46 | 0.0314 (7) | 0.0281 (7) | 0.0280 (7) | −0.0029 (6) | −0.0059 (5) | −0.0023 (6) |
C47 | 0.0252 (7) | 0.0313 (8) | 0.0331 (7) | 0.0031 (6) | −0.0090 (5) | −0.0107 (6) |
O41 | 0.0398 (6) | 0.0417 (6) | 0.0260 (5) | −0.0015 (5) | −0.0063 (4) | −0.0062 (4) |
O42 | 0.0631 (8) | 0.0510 (7) | 0.0516 (7) | −0.0211 (6) | −0.0090 (6) | −0.0239 (6) |
C48 | 0.0876 (15) | 0.0710 (14) | 0.0296 (9) | 0.0081 (11) | −0.0063 (9) | −0.0081 (9) |
O51 | 0.0338 (5) | 0.0334 (6) | 0.0341 (6) | −0.0057 (4) | −0.0042 (4) | −0.0090 (5) |
O61 | 0.0363 (6) | 0.0333 (6) | 0.0340 (6) | −0.0066 (5) | −0.0034 (4) | −0.0104 (5) |
N11—C12 | 1.4845 (18) | C242—C243 | 1.375 (2) |
N11—C16 | 1.4917 (17) | C242—H242 | 0.9500 |
N11—H11 | 0.948 (16) | C243—C244 | 1.377 (2) |
N11—H12 | 0.918 (16) | C243—H243 | 0.9500 |
C12—C13 | 1.5131 (18) | C244—C245 | 1.364 (2) |
C12—H12A | 0.9900 | C244—O244 | 1.3784 (17) |
C12—H12B | 0.9900 | C245—C246 | 1.394 (2) |
C13—N14 | 1.4617 (16) | C245—H245 | 0.9500 |
C13—H13A | 0.9900 | C246—H246 | 0.9500 |
C13—H13B | 0.9900 | O244—C247 | 1.411 (2) |
N14—C141 | 1.4216 (16) | C247—H27A | 0.9800 |
N14—C15 | 1.4677 (16) | C247—H27B | 0.9800 |
C15—C16 | 1.5128 (18) | C247—H27C | 0.9800 |
C15—H15A | 0.9900 | C31—C36 | 1.3852 (19) |
C15—H15B | 0.9900 | C31—C32 | 1.391 (2) |
C16—H16A | 0.9900 | C31—C37 | 1.5072 (18) |
C16—H16B | 0.9900 | C32—C33 | 1.383 (2) |
C141—C146 | 1.3917 (18) | C32—H32 | 0.9500 |
C141—C142 | 1.3963 (19) | C33—C34 | 1.385 (2) |
C142—C143 | 1.380 (2) | C33—H33 | 0.9500 |
C142—H142 | 0.9500 | C34—C35 | 1.387 (2) |
C143—C144 | 1.381 (2) | C34—C38 | 1.511 (2) |
C143—H143 | 0.9500 | C35—C36 | 1.3865 (19) |
C144—O144 | 1.3771 (17) | C35—H35 | 0.9500 |
C144—C145 | 1.379 (2) | C36—H36 | 0.9500 |
C145—C146 | 1.3870 (19) | C37—O32 | 1.2424 (17) |
C145—H145 | 0.9500 | C37—O31 | 1.2678 (17) |
C146—H146 | 0.9500 | C38—H38A | 0.9800 |
O144—C147 | 1.406 (2) | C38—H38B | 0.9800 |
C147—H17A | 0.9800 | C38—H38C | 0.9800 |
C147—H17B | 0.9800 | C41—C46 | 1.3885 (19) |
C147—H17C | 0.9800 | C41—C42 | 1.390 (2) |
N21—C22 | 1.4874 (18) | C41—C47 | 1.5043 (18) |
N21—C26 | 1.4902 (17) | C42—C43 | 1.389 (2) |
N21—H21 | 0.950 (16) | C42—H42 | 0.9500 |
N21—H22 | 0.905 (16) | C43—C44 | 1.382 (2) |
C22—C23 | 1.5144 (18) | C43—H43 | 0.9500 |
C22—H22A | 0.9900 | C44—C45 | 1.387 (2) |
C22—H22B | 0.9900 | C44—C48 | 1.512 (2) |
C23—N24 | 1.4706 (16) | C45—C46 | 1.3876 (19) |
C23—H23A | 0.9900 | C45—H45 | 0.9500 |
C23—H23B | 0.9900 | C46—H46 | 0.9500 |
N24—C241 | 1.4251 (16) | C47—O42 | 1.2392 (17) |
N24—C25 | 1.4646 (16) | C47—O41 | 1.2705 (18) |
C25—C26 | 1.5113 (18) | C48—H48A | 0.9800 |
C25—H25A | 0.9900 | C48—H48B | 0.9800 |
C25—H25B | 0.9900 | C48—H48C | 0.9800 |
C26—H26A | 0.9900 | O51—H51 | 0.89 (2) |
C26—H26B | 0.9900 | O51—H52 | 0.918 (19) |
C241—C246 | 1.381 (2) | O61—H61 | 0.904 (19) |
C241—C242 | 1.390 (2) | O61—H62 | 0.92 (2) |
C12—N11—C16 | 109.88 (10) | N21—C26—H26A | 109.7 |
C12—N11—H11 | 110.3 (9) | C25—C26—H26A | 109.7 |
C16—N11—H11 | 112.7 (9) | N21—C26—H26B | 109.7 |
C12—N11—H12 | 108.3 (10) | C25—C26—H26B | 109.7 |
C16—N11—H12 | 110.4 (9) | H26A—C26—H26B | 108.2 |
H11—N11—H12 | 105.1 (13) | C246—C241—C242 | 116.53 (13) |
N11—C12—C13 | 110.18 (11) | C246—C241—N24 | 123.04 (12) |
N11—C12—H12A | 109.6 | C242—C241—N24 | 120.40 (12) |
C13—C12—H12A | 109.6 | C243—C242—C241 | 121.40 (15) |
N11—C12—H12B | 109.6 | C243—C242—H242 | 119.3 |
C13—C12—H12B | 109.6 | C241—C242—H242 | 119.3 |
H12A—C12—H12B | 108.1 | C242—C243—C244 | 121.06 (15) |
N14—C13—C12 | 112.02 (11) | C242—C243—H243 | 119.5 |
N14—C13—H13A | 109.2 | C244—C243—H243 | 119.5 |
C12—C13—H13A | 109.2 | C245—C244—C243 | 118.89 (14) |
N14—C13—H13B | 109.2 | C245—C244—O244 | 125.06 (15) |
C12—C13—H13B | 109.2 | C243—C244—O244 | 116.05 (14) |
H13A—C13—H13B | 107.9 | C244—C245—C246 | 119.87 (15) |
C141—N14—C13 | 115.21 (10) | C244—C245—H245 | 120.1 |
C141—N14—C15 | 115.05 (10) | C246—C245—H245 | 120.1 |
C13—N14—C15 | 111.21 (10) | C241—C246—C245 | 122.22 (14) |
N14—C15—C16 | 111.37 (11) | C241—C246—H246 | 118.9 |
N14—C15—H15A | 109.4 | C245—C246—H246 | 118.9 |
C16—C15—H15A | 109.4 | C244—O244—C247 | 117.82 (14) |
N14—C15—H15B | 109.4 | O244—C247—H27A | 109.5 |
C16—C15—H15B | 109.4 | O244—C247—H27B | 109.5 |
H15A—C15—H15B | 108.0 | H27A—C247—H27B | 109.5 |
N11—C16—C15 | 109.93 (11) | O244—C247—H27C | 109.5 |
N11—C16—H16A | 109.7 | H27A—C247—H27C | 109.5 |
C15—C16—H16A | 109.7 | H27B—C247—H27C | 109.5 |
N11—C16—H16B | 109.7 | C36—C31—C32 | 118.79 (13) |
C15—C16—H16B | 109.7 | C36—C31—C37 | 121.27 (12) |
H16A—C16—H16B | 108.2 | C32—C31—C37 | 119.93 (13) |
C146—C141—C142 | 117.13 (12) | C33—C32—C31 | 120.19 (14) |
C146—C141—N14 | 120.41 (11) | C33—C32—H32 | 119.9 |
C142—C141—N14 | 122.38 (12) | C31—C32—H32 | 119.9 |
C143—C142—C141 | 120.97 (13) | C32—C33—C34 | 121.44 (15) |
C143—C142—H142 | 119.5 | C32—C33—H33 | 119.3 |
C141—C142—H142 | 119.5 | C34—C33—H33 | 119.3 |
C142—C143—C144 | 121.15 (14) | C33—C34—C35 | 118.01 (14) |
C142—C143—H143 | 119.4 | C33—C34—C38 | 121.66 (16) |
C144—C143—H143 | 119.4 | C35—C34—C38 | 120.33 (16) |
O144—C144—C145 | 125.25 (14) | C36—C35—C34 | 121.09 (14) |
O144—C144—C143 | 115.95 (13) | C36—C35—H35 | 119.5 |
C145—C144—C143 | 118.79 (13) | C34—C35—H35 | 119.5 |
C144—C145—C146 | 120.21 (13) | C31—C36—C35 | 120.44 (14) |
C144—C145—H145 | 119.9 | C31—C36—H36 | 119.8 |
C146—C145—H145 | 119.9 | C35—C36—H36 | 119.8 |
C145—C146—C141 | 121.74 (13) | O32—C37—O31 | 124.57 (13) |
C145—C146—H146 | 119.1 | O32—C37—C31 | 117.82 (13) |
C141—C146—H146 | 119.1 | O31—C37—C31 | 117.61 (12) |
C144—O144—C147 | 117.49 (13) | C34—C38—H38A | 109.5 |
O144—C147—H17A | 109.5 | C34—C38—H38B | 109.5 |
O144—C147—H17B | 109.5 | H38A—C38—H38B | 109.5 |
H17A—C147—H17B | 109.5 | C34—C38—H38C | 109.5 |
O144—C147—H17C | 109.5 | H38A—C38—H38C | 109.5 |
H17A—C147—H17C | 109.5 | H38B—C38—H38C | 109.5 |
H17B—C147—H17C | 109.5 | C46—C41—C42 | 118.81 (12) |
C22—N21—C26 | 109.64 (10) | C46—C41—C47 | 121.00 (12) |
C22—N21—H21 | 110.7 (9) | C42—C41—C47 | 120.18 (12) |
C26—N21—H21 | 111.8 (9) | C43—C42—C41 | 120.21 (14) |
C22—N21—H22 | 106.9 (10) | C43—C42—H42 | 119.9 |
C26—N21—H22 | 110.2 (10) | C41—C42—H42 | 119.9 |
H21—N21—H22 | 107.5 (13) | C44—C43—C42 | 121.24 (15) |
N21—C22—C23 | 109.97 (11) | C44—C43—H43 | 119.4 |
N21—C22—H22A | 109.7 | C42—C43—H43 | 119.4 |
C23—C22—H22A | 109.7 | C43—C44—C45 | 118.30 (14) |
N21—C22—H22B | 109.7 | C43—C44—C48 | 121.61 (16) |
C23—C22—H22B | 109.7 | C45—C44—C48 | 120.08 (16) |
H22A—C22—H22B | 108.2 | C44—C45—C46 | 121.03 (14) |
N24—C23—C22 | 112.03 (11) | C44—C45—H45 | 119.5 |
N24—C23—H23A | 109.2 | C46—C45—H45 | 119.5 |
C22—C23—H23A | 109.2 | C45—C46—C41 | 120.40 (13) |
N24—C23—H23B | 109.2 | C45—C46—H46 | 119.8 |
C22—C23—H23B | 109.2 | C41—C46—H46 | 119.8 |
H23A—C23—H23B | 107.9 | O42—C47—O41 | 123.97 (13) |
C241—N24—C25 | 114.88 (10) | O42—C47—C41 | 117.63 (14) |
C241—N24—C23 | 113.35 (10) | O41—C47—C41 | 118.40 (12) |
C25—N24—C23 | 110.62 (10) | C44—C48—H48A | 109.5 |
N24—C25—C26 | 111.20 (11) | C44—C48—H48B | 109.5 |
N24—C25—H25A | 109.4 | H48A—C48—H48B | 109.5 |
C26—C25—H25A | 109.4 | C44—C48—H48C | 109.5 |
N24—C25—H25B | 109.4 | H48A—C48—H48C | 109.5 |
C26—C25—H25B | 109.4 | H48B—C48—H48C | 109.5 |
H25A—C25—H25B | 108.0 | H51—O51—H52 | 105.5 (16) |
N21—C26—C25 | 110.03 (10) | H61—O61—H62 | 106.6 (16) |
C16—N11—C12—C13 | −57.49 (14) | C241—C242—C243—C244 | −0.2 (3) |
N11—C12—C13—N14 | 56.22 (15) | C242—C243—C244—C245 | 1.7 (3) |
C12—C13—N14—C141 | 171.77 (11) | C242—C243—C244—O244 | −177.89 (16) |
C12—C13—N14—C15 | −55.02 (15) | C243—C244—C245—C246 | −1.6 (3) |
C141—N14—C15—C16 | −171.14 (10) | O244—C244—C245—C246 | 177.91 (16) |
C13—N14—C15—C16 | 55.58 (14) | C242—C241—C246—C245 | 1.3 (2) |
C12—N11—C16—C15 | 58.26 (14) | N24—C241—C246—C245 | 179.21 (14) |
N14—C15—C16—N11 | −57.35 (14) | C244—C245—C246—C241 | 0.1 (3) |
C13—N14—C141—C146 | 177.99 (12) | C245—C244—O244—C247 | 0.4 (3) |
C15—N14—C141—C146 | 46.58 (16) | C243—C244—O244—C247 | 179.97 (18) |
C13—N14—C141—C142 | −5.45 (18) | C36—C31—C32—C33 | 1.5 (2) |
C15—N14—C141—C142 | −136.85 (14) | C37—C31—C32—C33 | −177.47 (13) |
C146—C141—C142—C143 | 1.3 (2) | C31—C32—C33—C34 | −0.6 (2) |
N14—C141—C142—C143 | −175.37 (14) | C32—C33—C34—C35 | −1.2 (2) |
C141—C142—C143—C144 | −1.2 (3) | C32—C33—C34—C38 | 178.95 (15) |
C142—C143—C144—O144 | −179.29 (15) | C33—C34—C35—C36 | 2.1 (2) |
C142—C143—C144—C145 | 0.2 (3) | C38—C34—C35—C36 | −178.08 (15) |
O144—C144—C145—C146 | −179.99 (15) | C32—C31—C36—C35 | −0.7 (2) |
C143—C144—C145—C146 | 0.6 (2) | C37—C31—C36—C35 | 178.31 (12) |
C144—C145—C146—C141 | −0.4 (2) | C34—C35—C36—C31 | −1.1 (2) |
C142—C141—C146—C145 | −0.5 (2) | C36—C31—C37—O32 | 168.27 (13) |
N14—C141—C146—C145 | 176.20 (13) | C32—C31—C37—O32 | −12.75 (19) |
C145—C144—O144—C147 | −4.8 (3) | C36—C31—C37—O31 | −12.27 (18) |
C143—C144—O144—C147 | 174.67 (17) | C32—C31—C37—O31 | 166.71 (13) |
C26—N21—C22—C23 | −57.46 (14) | C46—C41—C42—C43 | 0.7 (2) |
N21—C22—C23—N24 | 56.44 (15) | C47—C41—C42—C43 | 179.74 (13) |
C22—C23—N24—C241 | 173.71 (11) | C41—C42—C43—C44 | −0.5 (2) |
C22—C23—N24—C25 | −55.59 (14) | C42—C43—C44—C45 | 0.2 (2) |
C241—N24—C25—C26 | −173.81 (10) | C42—C43—C44—C48 | 179.55 (15) |
C23—N24—C25—C26 | 56.30 (13) | C43—C44—C45—C46 | 0.0 (2) |
C22—N21—C26—C25 | 58.68 (14) | C48—C44—C45—C46 | −179.38 (15) |
N24—C25—C26—N21 | −58.38 (14) | C44—C45—C46—C41 | 0.2 (2) |
C25—N24—C241—C246 | 6.68 (18) | C42—C41—C46—C45 | −0.5 (2) |
C23—N24—C241—C246 | 135.22 (14) | C47—C41—C46—C45 | −179.56 (12) |
C25—N24—C241—C242 | −175.46 (13) | C46—C41—C47—O42 | 175.08 (13) |
C23—N24—C241—C242 | −46.92 (17) | C42—C41—C47—O42 | −3.96 (19) |
C246—C241—C242—C243 | −1.2 (2) | C46—C41—C47—O41 | −4.69 (19) |
N24—C241—C242—C243 | −179.21 (15) | C42—C41—C47—O41 | 176.28 (12) |
Cg1 and Cg2 represent the centroids of the C31–C36 and C41–C46 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O31 | 0.946 (16) | 1.793 (16) | 2.7366 (16) | 174.5 (13) |
N11—H12···O61i | 0.917 (15) | 1.891 (15) | 2.7969 (16) | 169.2 (13) |
N21—H21···O41 | 0.949 (16) | 1.813 (16) | 2.7592 (16) | 174.1 (14) |
N21—H22···O51i | 0.904 (15) | 1.909 (15) | 2.8047 (16) | 170.9 (13) |
O51—H51···O41ii | 0.89 (2) | 1.89 (2) | 2.7712 (16) | 170.0 (18) |
O51—H52···O32 | 0.918 (18) | 1.739 (18) | 2.6539 (16) | 174.3 (15) |
O61—H61···O42 | 0.906 (19) | 1.733 (19) | 2.6315 (16) | 171.2 (15) |
O61—H62···O31 | 0.92 (2) | 1.85 (2) | 2.7593 (15) | 169.1 (19) |
C22—H22B···O41iii | 0.99 | 2.56 | 3.5266 (19) | 167 |
C142—H142···Cg1i | 0.95 | 2.83 | 3.5976 (16) | 138 |
C146—H146···Cg2iv | 0.95 | 2.73 | 3.5478 (16) | 145 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+1, −y, −z+1; (iv) −x+1, −y+1, −z+1. |
2C11H17N2O+·C8H4O42− | Dx = 1.332 Mg m−3 |
Mr = 550.64 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, Pna21 | Cell parameters from 10053 reflections |
a = 17.8424 (4) Å | θ = 5.0–70.1° |
b = 8.8124 (2) Å | µ = 0.76 mm−1 |
c = 34.9337 (9) Å | T = 180 K |
V = 5492.8 (2) Å3 | Plate, colourless |
Z = 8 | 0.26 × 0.24 × 0.04 mm |
F(000) = 2352 |
Bruker D8 Venture dual source diffractometer | 10053 independent reflections |
Radiation source: microsource | 9727 reflections with I > 2σ(I) |
Multilayer optics monochromator | Rint = 0.031 |
φ and ω scans | θmax = 70.1°, θmin = 5.0° |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | h = −21→21 |
Tmin = 0.814, Tmax = 0.942 | k = −10→10 |
36488 measured reflections | l = −41→42 |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0511P)2 + 1.5447P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.037 | (Δ/σ)max = 0.001 |
wR(F2) = 0.098 | Δρmax = 0.27 e Å−3 |
S = 1.07 | Δρmin = −0.17 e Å−3 |
10053 reflections | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
750 parameters | Extinction coefficient: 0.0018 (2) |
1 restraint | Absolute structure: Flack x determined using 4511 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: dual | Absolute structure parameter: 0.45 (5) |
Hydrogen site location: mixed |
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 | ||
N11 | 0.87134 (14) | 0.7550 (3) | 0.46161 (8) | 0.0272 (5) | |
H11 | 0.8642 (18) | 0.778 (4) | 0.4891 (11) | 0.033* | |
H12 | 0.909 (2) | 0.799 (4) | 0.4563 (10) | 0.033* | |
C12 | 0.80552 (16) | 0.8091 (3) | 0.43903 (9) | 0.0320 (6) | |
H12A | 0.8019 | 0.9209 | 0.4409 | 0.038* | |
H12B | 0.7590 | 0.7650 | 0.4498 | 0.038* | |
C13 | 0.81286 (17) | 0.7636 (3) | 0.39740 (8) | 0.0285 (6) | |
H13A | 0.7669 | 0.7931 | 0.3834 | 0.034* | |
H13B | 0.8558 | 0.8178 | 0.3857 | 0.034* | |
N14 | 0.82434 (12) | 0.5999 (2) | 0.39400 (6) | 0.0235 (5) | |
C15 | 0.89338 (15) | 0.5558 (3) | 0.41323 (8) | 0.0267 (6) | |
H15A | 0.9362 | 0.6126 | 0.4023 | 0.032* | |
H15B | 0.9026 | 0.4460 | 0.4095 | 0.032* | |
C16 | 0.88572 (16) | 0.5909 (3) | 0.45548 (8) | 0.0297 (6) | |
H16A | 0.8439 | 0.5310 | 0.4664 | 0.036* | |
H16B | 0.9323 | 0.5612 | 0.4689 | 0.036* | |
C141 | 0.81224 (15) | 0.5400 (3) | 0.35683 (7) | 0.0230 (5) | |
C142 | 0.73982 (16) | 0.5497 (4) | 0.34152 (9) | 0.0328 (6) | |
H142 | 0.7014 | 0.5990 | 0.3557 | 0.039* | |
C143 | 0.72360 (18) | 0.4888 (4) | 0.30617 (10) | 0.0362 (7) | |
H143 | 0.6742 | 0.4973 | 0.2962 | 0.043* | |
C144 | 0.77848 (17) | 0.4148 (3) | 0.28482 (8) | 0.0304 (6) | |
C145 | 0.84993 (16) | 0.4047 (3) | 0.29947 (8) | 0.0298 (6) | |
H145 | 0.8880 | 0.3546 | 0.2853 | 0.036* | |
C146 | 0.86657 (15) | 0.4677 (3) | 0.33516 (8) | 0.0269 (6) | |
H146 | 0.9163 | 0.4609 | 0.3448 | 0.032* | |
O144 | 0.75569 (14) | 0.3577 (3) | 0.25005 (7) | 0.0448 (6) | |
C147 | 0.80702 (19) | 0.2601 (4) | 0.23098 (9) | 0.0379 (7) | |
H17A | 0.8533 | 0.3157 | 0.2254 | 0.057* | |
H17B | 0.7847 | 0.2242 | 0.2070 | 0.057* | |
H17C | 0.8185 | 0.1730 | 0.2474 | 0.057* | |
N21 | 0.62871 (13) | 0.7455 (3) | 1.03620 (8) | 0.0285 (5) | |
H21 | 0.6222 (19) | 0.722 (4) | 1.0088 (11) | 0.034* | |
H22 | 0.676 (2) | 0.689 (4) | 1.0436 (10) | 0.034* | |
C22 | 0.56305 (16) | 0.6921 (3) | 1.05899 (9) | 0.0326 (6) | |
H22A | 0.5589 | 0.5804 | 1.0569 | 0.039* | |
H22B | 0.5166 | 0.7372 | 1.0485 | 0.039* | |
C23 | 0.57104 (16) | 0.7362 (3) | 1.10062 (8) | 0.0286 (6) | |
H23A | 0.5250 | 0.7077 | 1.1147 | 0.034* | |
H23B | 0.6136 | 0.6803 | 1.1121 | 0.034* | |
N24 | 0.58379 (12) | 0.8995 (2) | 1.10434 (6) | 0.0237 (5) | |
C25 | 0.65261 (16) | 0.9418 (3) | 1.08482 (8) | 0.0274 (6) | |
H25A | 0.6952 | 0.8828 | 1.0953 | 0.033* | |
H25B | 0.6630 | 1.0510 | 1.0888 | 0.033* | |
C26 | 0.64373 (17) | 0.9093 (3) | 1.04258 (8) | 0.0310 (6) | |
H26A | 0.6018 | 0.9701 | 1.0322 | 0.037* | |
H26B | 0.6900 | 0.9390 | 1.0289 | 0.037* | |
C241 | 0.57153 (15) | 0.9597 (3) | 1.14149 (8) | 0.0230 (5) | |
C242 | 0.49942 (16) | 0.9532 (3) | 1.15652 (9) | 0.0304 (6) | |
H242 | 0.4610 | 0.9041 | 1.1423 | 0.036* | |
C243 | 0.48233 (17) | 1.0164 (4) | 1.19163 (10) | 0.0356 (7) | |
H243 | 0.4327 | 1.0100 | 1.2013 | 0.043* | |
C244 | 0.53764 (17) | 1.0895 (3) | 1.21301 (8) | 0.0295 (6) | |
C245 | 0.60958 (16) | 1.0977 (3) | 1.19861 (8) | 0.0289 (6) | |
H245 | 0.6477 | 1.1476 | 1.2128 | 0.035* | |
C246 | 0.62640 (15) | 1.0326 (3) | 1.16312 (8) | 0.0273 (6) | |
H246 | 0.6762 | 1.0382 | 1.1536 | 0.033* | |
O244 | 0.51493 (13) | 1.1490 (3) | 1.24745 (6) | 0.0407 (5) | |
C247 | 0.5690 (2) | 1.2308 (4) | 1.26905 (10) | 0.0433 (8) | |
H27A | 0.6094 | 1.1621 | 1.2769 | 0.065* | |
H27B | 0.5451 | 1.2741 | 1.2918 | 0.065* | |
H27C | 0.5898 | 1.3127 | 1.2533 | 0.065* | |
N31 | 0.59650 (13) | 0.7174 (3) | 0.52626 (7) | 0.0261 (5) | |
H31 | 0.5784 (19) | 0.718 (4) | 0.5010 (10) | 0.031* | |
H32 | 0.640 (2) | 0.774 (4) | 0.5272 (10) | 0.031* | |
C32 | 0.61659 (16) | 0.5555 (3) | 0.53320 (8) | 0.0291 (6) | |
H32A | 0.6589 | 0.5267 | 0.5164 | 0.035* | |
H32B | 0.5733 | 0.4901 | 0.5267 | 0.035* | |
C33 | 0.63847 (16) | 0.5297 (3) | 0.57459 (8) | 0.0286 (6) | |
H33A | 0.6491 | 0.4207 | 0.5788 | 0.034* | |
H33B | 0.6845 | 0.5878 | 0.5805 | 0.034* | |
N34 | 0.57770 (13) | 0.5783 (3) | 0.59990 (6) | 0.0247 (5) | |
C35 | 0.56205 (17) | 0.7403 (3) | 0.59425 (9) | 0.0284 (6) | |
H35A | 0.6076 | 0.8001 | 0.6001 | 0.034* | |
H35B | 0.5220 | 0.7727 | 0.6121 | 0.034* | |
C36 | 0.53783 (16) | 0.7706 (3) | 0.55351 (8) | 0.0291 (6) | |
H36A | 0.4901 | 0.7172 | 0.5483 | 0.035* | |
H36B | 0.5293 | 0.8808 | 0.5499 | 0.035* | |
C341 | 0.58380 (15) | 0.5329 (3) | 0.63868 (8) | 0.0245 (5) | |
C342 | 0.64566 (17) | 0.4557 (3) | 0.65329 (8) | 0.0312 (6) | |
H342 | 0.6874 | 0.4372 | 0.6371 | 0.037* | |
C343 | 0.64786 (19) | 0.4050 (4) | 0.69096 (9) | 0.0377 (7) | |
H343 | 0.6901 | 0.3504 | 0.7001 | 0.045* | |
C344 | 0.58839 (19) | 0.4345 (3) | 0.71498 (8) | 0.0342 (7) | |
C345 | 0.52757 (19) | 0.5138 (4) | 0.70097 (10) | 0.0395 (7) | |
H345 | 0.4868 | 0.5360 | 0.7176 | 0.047* | |
C346 | 0.52465 (17) | 0.5612 (4) | 0.66353 (9) | 0.0351 (7) | |
H346 | 0.4817 | 0.6140 | 0.6545 | 0.042* | |
O344 | 0.58749 (16) | 0.3975 (3) | 0.75337 (6) | 0.0499 (6) | |
C347 | 0.6144 (2) | 0.2511 (4) | 0.76343 (10) | 0.0434 (8) | |
H37A | 0.5844 | 0.1736 | 0.7504 | 0.065* | |
H37B | 0.6103 | 0.2372 | 0.7912 | 0.065* | |
H37C | 0.6670 | 0.2416 | 0.7557 | 0.065* | |
N41 | 0.35347 (13) | 0.7834 (3) | 0.96744 (7) | 0.0284 (5) | |
H41 | 0.3333 (19) | 0.780 (4) | 0.9940 (11) | 0.034* | |
H42 | 0.394 (2) | 0.723 (4) | 0.9660 (10) | 0.034* | |
C42 | 0.37614 (16) | 0.9436 (3) | 0.96097 (9) | 0.0311 (6) | |
H42A | 0.4193 | 0.9683 | 0.9777 | 0.037* | |
H42B | 0.3342 | 1.0115 | 0.9680 | 0.037* | |
C43 | 0.39750 (16) | 0.9709 (3) | 0.91972 (9) | 0.0309 (6) | |
H43A | 0.4100 | 1.0794 | 0.9160 | 0.037* | |
H43B | 0.4424 | 0.9101 | 0.9132 | 0.037* | |
N44 | 0.33606 (13) | 0.9291 (2) | 0.89465 (7) | 0.0267 (5) | |
C45 | 0.31864 (16) | 0.7675 (3) | 0.89905 (9) | 0.0306 (6) | |
H45A | 0.3634 | 0.7062 | 0.8926 | 0.037* | |
H45B | 0.2779 | 0.7391 | 0.8812 | 0.037* | |
C46 | 0.29473 (16) | 0.7340 (3) | 0.93967 (10) | 0.0315 (6) | |
H46A | 0.2472 | 0.7877 | 0.9453 | 0.038* | |
H46B | 0.2857 | 0.6237 | 0.9426 | 0.038* | |
C441 | 0.33856 (16) | 0.9847 (3) | 0.85647 (8) | 0.0266 (6) | |
C442 | 0.39903 (16) | 1.0619 (3) | 0.84117 (8) | 0.0294 (6) | |
H442 | 0.4442 | 1.0682 | 0.8555 | 0.035* | |
C443 | 0.39546 (17) | 1.1310 (3) | 0.80501 (9) | 0.0321 (6) | |
H443 | 0.4375 | 1.1848 | 0.7953 | 0.038* | |
C444 | 0.33068 (17) | 1.1208 (3) | 0.78350 (8) | 0.0322 (6) | |
C445 | 0.27056 (18) | 1.0369 (4) | 0.79782 (9) | 0.0351 (7) | |
H445 | 0.2265 | 1.0252 | 0.7828 | 0.042* | |
C446 | 0.27444 (16) | 0.9710 (3) | 0.83348 (9) | 0.0315 (6) | |
H446 | 0.2327 | 0.9150 | 0.8427 | 0.038* | |
O447 | 0.31901 (13) | 1.1870 (2) | 0.74835 (6) | 0.0407 (5) | |
C447 | 0.3794 (2) | 1.2730 (4) | 0.73265 (10) | 0.0438 (8) | |
H47A | 0.4236 | 1.2078 | 0.7299 | 0.066* | |
H47B | 0.3912 | 1.3579 | 0.7497 | 0.066* | |
H47C | 0.3649 | 1.3123 | 0.7075 | 0.066* | |
C51 | 0.77813 (14) | 0.9274 (3) | 0.58429 (7) | 0.0218 (5) | |
C52 | 0.72145 (14) | 1.0348 (3) | 0.59017 (8) | 0.0230 (5) | |
C53 | 0.70626 (16) | 1.0837 (3) | 0.62739 (8) | 0.0290 (6) | |
H53 | 0.6675 | 1.1555 | 0.6316 | 0.035* | |
C54 | 0.74701 (18) | 1.0288 (3) | 0.65831 (9) | 0.0343 (6) | |
H54 | 0.7356 | 1.0620 | 0.6835 | 0.041* | |
C55 | 0.80426 (18) | 0.9257 (3) | 0.65224 (8) | 0.0335 (6) | |
H55 | 0.8331 | 0.8893 | 0.6732 | 0.040* | |
C56 | 0.81934 (15) | 0.8757 (3) | 0.61533 (8) | 0.0269 (6) | |
H56 | 0.8586 | 0.8047 | 0.6113 | 0.032* | |
C57 | 0.79259 (14) | 0.8587 (3) | 0.54501 (7) | 0.0216 (5) | |
O51 | 0.85883 (12) | 0.8253 (3) | 0.53699 (6) | 0.0442 (6) | |
O52 | 0.73774 (11) | 0.8367 (3) | 0.52362 (6) | 0.0339 (5) | |
C58 | 0.67939 (15) | 1.1118 (3) | 0.55757 (8) | 0.0258 (6) | |
O53 | 0.72016 (11) | 1.1881 (2) | 0.53494 (6) | 0.0315 (4) | |
O54 | 0.61057 (11) | 1.1038 (3) | 0.55663 (7) | 0.0431 (6) | |
C61 | 0.53754 (14) | 0.5763 (3) | 0.91267 (7) | 0.0203 (5) | |
C62 | 0.48063 (14) | 0.4705 (3) | 0.90566 (7) | 0.0210 (5) | |
C63 | 0.46708 (15) | 0.4225 (3) | 0.86845 (8) | 0.0261 (6) | |
H63 | 0.4280 | 0.3518 | 0.8637 | 0.031* | |
C64 | 0.50944 (16) | 0.4758 (3) | 0.83823 (8) | 0.0289 (6) | |
H64 | 0.4992 | 0.4423 | 0.8129 | 0.035* | |
C65 | 0.56708 (16) | 0.5782 (3) | 0.84487 (8) | 0.0290 (6) | |
H65 | 0.5968 | 0.6142 | 0.8242 | 0.035* | |
C66 | 0.58113 (15) | 0.6279 (3) | 0.88205 (8) | 0.0245 (5) | |
H66 | 0.6208 | 0.6976 | 0.8866 | 0.029* | |
C67 | 0.55033 (15) | 0.6439 (3) | 0.95187 (7) | 0.0234 (5) | |
O61 | 0.61608 (11) | 0.6799 (3) | 0.96078 (6) | 0.0408 (6) | |
O62 | 0.49458 (10) | 0.6629 (2) | 0.97323 (6) | 0.0325 (5) | |
C68 | 0.43777 (14) | 0.3927 (3) | 0.93738 (8) | 0.0237 (5) | |
O63 | 0.47775 (10) | 0.3110 (2) | 0.95979 (6) | 0.0296 (4) | |
O64 | 0.36920 (11) | 0.4038 (3) | 0.93907 (7) | 0.0391 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0225 (12) | 0.0352 (14) | 0.0239 (13) | −0.0028 (9) | 0.0018 (9) | −0.0044 (10) |
C12 | 0.0274 (13) | 0.0363 (16) | 0.0322 (15) | 0.0080 (12) | −0.0026 (12) | −0.0077 (12) |
C13 | 0.0339 (15) | 0.0227 (13) | 0.0289 (16) | 0.0054 (11) | −0.0026 (11) | −0.0008 (11) |
N14 | 0.0225 (11) | 0.0220 (11) | 0.0260 (11) | 0.0025 (8) | −0.0030 (9) | 0.0003 (9) |
C15 | 0.0245 (13) | 0.0246 (13) | 0.0310 (15) | 0.0054 (11) | −0.0033 (11) | 0.0005 (11) |
C16 | 0.0307 (14) | 0.0315 (15) | 0.0270 (15) | −0.0028 (12) | −0.0048 (11) | 0.0054 (11) |
C141 | 0.0237 (13) | 0.0200 (12) | 0.0254 (13) | −0.0003 (10) | −0.0019 (10) | 0.0027 (10) |
C142 | 0.0214 (13) | 0.0361 (15) | 0.0408 (17) | 0.0055 (11) | −0.0035 (12) | −0.0078 (13) |
C143 | 0.0283 (15) | 0.0392 (17) | 0.0410 (18) | 0.0071 (13) | −0.0119 (13) | −0.0059 (14) |
C144 | 0.0372 (15) | 0.0284 (14) | 0.0257 (14) | 0.0041 (12) | −0.0049 (11) | 0.0011 (11) |
C145 | 0.0313 (15) | 0.0303 (14) | 0.0279 (14) | 0.0047 (12) | 0.0035 (11) | 0.0003 (11) |
C146 | 0.0227 (13) | 0.0294 (14) | 0.0286 (14) | 0.0008 (10) | −0.0016 (10) | 0.0011 (11) |
O144 | 0.0509 (14) | 0.0496 (13) | 0.0339 (12) | 0.0120 (11) | −0.0116 (10) | −0.0124 (10) |
C147 | 0.0454 (18) | 0.0378 (17) | 0.0304 (17) | −0.0048 (14) | 0.0010 (13) | −0.0046 (13) |
N21 | 0.0239 (12) | 0.0360 (14) | 0.0255 (13) | 0.0028 (10) | −0.0014 (9) | −0.0068 (10) |
C22 | 0.0287 (14) | 0.0328 (16) | 0.0363 (16) | −0.0043 (12) | 0.0029 (12) | −0.0096 (12) |
C23 | 0.0308 (14) | 0.0245 (14) | 0.0303 (16) | −0.0054 (11) | 0.0044 (11) | −0.0027 (11) |
N24 | 0.0243 (11) | 0.0232 (11) | 0.0237 (11) | −0.0015 (9) | 0.0022 (8) | −0.0015 (8) |
C25 | 0.0307 (14) | 0.0270 (13) | 0.0245 (14) | −0.0036 (11) | 0.0073 (11) | −0.0010 (10) |
C26 | 0.0324 (15) | 0.0352 (16) | 0.0254 (14) | 0.0030 (12) | 0.0029 (11) | 0.0037 (12) |
C241 | 0.0246 (12) | 0.0215 (12) | 0.0228 (13) | 0.0015 (10) | 0.0005 (10) | 0.0023 (10) |
C242 | 0.0252 (13) | 0.0311 (14) | 0.0349 (16) | −0.0031 (11) | −0.0001 (11) | −0.0046 (12) |
C243 | 0.0264 (15) | 0.0391 (16) | 0.0415 (18) | −0.0004 (13) | 0.0109 (12) | −0.0053 (13) |
C244 | 0.0362 (15) | 0.0254 (14) | 0.0268 (14) | 0.0045 (12) | 0.0080 (11) | −0.0002 (11) |
C245 | 0.0323 (15) | 0.0278 (14) | 0.0265 (14) | −0.0031 (11) | −0.0011 (11) | −0.0015 (11) |
C246 | 0.0249 (13) | 0.0285 (14) | 0.0286 (14) | −0.0027 (11) | 0.0036 (10) | 0.0018 (11) |
O244 | 0.0462 (13) | 0.0436 (12) | 0.0324 (11) | 0.0027 (10) | 0.0121 (10) | −0.0096 (10) |
C247 | 0.064 (2) | 0.0368 (17) | 0.0291 (17) | 0.0086 (16) | −0.0008 (15) | −0.0085 (13) |
N31 | 0.0213 (11) | 0.0293 (12) | 0.0277 (12) | −0.0055 (10) | −0.0030 (9) | 0.0005 (9) |
C32 | 0.0314 (14) | 0.0299 (14) | 0.0261 (14) | 0.0022 (11) | 0.0014 (11) | −0.0025 (11) |
C33 | 0.0277 (14) | 0.0298 (14) | 0.0283 (14) | 0.0071 (11) | 0.0021 (11) | −0.0036 (11) |
N34 | 0.0249 (11) | 0.0250 (11) | 0.0243 (11) | 0.0035 (9) | −0.0006 (9) | −0.0028 (9) |
C35 | 0.0308 (14) | 0.0226 (13) | 0.0317 (15) | 0.0038 (11) | 0.0021 (11) | −0.0029 (11) |
C36 | 0.0255 (14) | 0.0298 (14) | 0.0321 (16) | 0.0002 (11) | −0.0011 (11) | 0.0015 (11) |
C341 | 0.0263 (13) | 0.0219 (12) | 0.0252 (13) | −0.0009 (10) | −0.0012 (10) | −0.0036 (10) |
C342 | 0.0304 (14) | 0.0353 (15) | 0.0280 (15) | 0.0096 (12) | 0.0045 (11) | −0.0021 (12) |
C343 | 0.0406 (17) | 0.0391 (17) | 0.0334 (16) | 0.0147 (13) | −0.0032 (13) | −0.0021 (13) |
C344 | 0.0477 (18) | 0.0302 (14) | 0.0246 (14) | 0.0027 (13) | 0.0026 (12) | −0.0023 (11) |
C345 | 0.0422 (17) | 0.0413 (17) | 0.0352 (17) | 0.0090 (14) | 0.0097 (13) | −0.0011 (13) |
C346 | 0.0304 (15) | 0.0411 (16) | 0.0337 (16) | 0.0101 (13) | 0.0030 (12) | 0.0018 (13) |
O344 | 0.0782 (18) | 0.0450 (12) | 0.0265 (11) | 0.0175 (12) | 0.0065 (11) | 0.0069 (10) |
C347 | 0.063 (2) | 0.0353 (17) | 0.0322 (18) | −0.0003 (15) | −0.0069 (15) | 0.0080 (13) |
N41 | 0.0229 (11) | 0.0298 (12) | 0.0323 (13) | 0.0036 (10) | 0.0035 (9) | 0.0000 (10) |
C42 | 0.0279 (14) | 0.0310 (15) | 0.0342 (15) | −0.0008 (11) | −0.0022 (11) | −0.0042 (12) |
C43 | 0.0274 (14) | 0.0315 (15) | 0.0337 (15) | −0.0063 (12) | −0.0032 (11) | −0.0015 (12) |
N44 | 0.0249 (11) | 0.0239 (11) | 0.0313 (12) | −0.0033 (9) | −0.0018 (9) | −0.0027 (9) |
C45 | 0.0286 (14) | 0.0253 (14) | 0.0379 (17) | −0.0005 (11) | −0.0013 (12) | −0.0059 (12) |
C46 | 0.0233 (13) | 0.0267 (14) | 0.0445 (18) | −0.0036 (11) | 0.0023 (12) | −0.0016 (12) |
C441 | 0.0272 (14) | 0.0242 (13) | 0.0282 (14) | 0.0005 (11) | 0.0009 (10) | −0.0065 (11) |
C442 | 0.0247 (13) | 0.0286 (14) | 0.0350 (16) | −0.0020 (11) | −0.0027 (11) | −0.0044 (11) |
C443 | 0.0319 (15) | 0.0301 (15) | 0.0342 (15) | −0.0029 (12) | 0.0024 (12) | −0.0029 (12) |
C444 | 0.0390 (16) | 0.0291 (14) | 0.0287 (14) | 0.0013 (12) | −0.0013 (12) | −0.0057 (11) |
C445 | 0.0330 (16) | 0.0376 (17) | 0.0346 (16) | 0.0006 (13) | −0.0079 (12) | −0.0075 (12) |
C446 | 0.0257 (14) | 0.0353 (15) | 0.0337 (15) | −0.0051 (11) | −0.0004 (11) | −0.0041 (12) |
O447 | 0.0459 (12) | 0.0435 (12) | 0.0328 (11) | 0.0014 (10) | −0.0040 (9) | 0.0028 (9) |
C447 | 0.058 (2) | 0.0386 (17) | 0.0344 (18) | 0.0009 (16) | 0.0035 (15) | 0.0054 (14) |
C51 | 0.0206 (12) | 0.0217 (12) | 0.0230 (13) | −0.0033 (10) | −0.0008 (10) | −0.0014 (10) |
C52 | 0.0206 (12) | 0.0213 (12) | 0.0271 (13) | −0.0047 (9) | 0.0028 (10) | −0.0021 (10) |
C53 | 0.0256 (14) | 0.0299 (14) | 0.0314 (15) | −0.0030 (11) | 0.0065 (11) | −0.0042 (11) |
C54 | 0.0424 (17) | 0.0340 (16) | 0.0266 (14) | −0.0041 (13) | 0.0063 (12) | −0.0063 (12) |
C55 | 0.0444 (17) | 0.0321 (14) | 0.0239 (14) | −0.0039 (12) | −0.0060 (12) | 0.0014 (11) |
C56 | 0.0273 (13) | 0.0232 (13) | 0.0303 (15) | 0.0014 (11) | −0.0001 (11) | −0.0009 (10) |
C57 | 0.0206 (12) | 0.0208 (12) | 0.0233 (13) | −0.0002 (9) | 0.0015 (10) | −0.0021 (10) |
O51 | 0.0259 (10) | 0.0750 (17) | 0.0317 (11) | 0.0149 (10) | −0.0033 (9) | −0.0179 (11) |
O52 | 0.0216 (10) | 0.0508 (13) | 0.0292 (10) | −0.0074 (9) | 0.0000 (8) | −0.0124 (9) |
C58 | 0.0206 (13) | 0.0235 (13) | 0.0334 (14) | 0.0003 (10) | −0.0014 (10) | −0.0036 (11) |
O53 | 0.0265 (10) | 0.0337 (11) | 0.0344 (11) | −0.0034 (8) | −0.0065 (8) | 0.0084 (9) |
O54 | 0.0178 (10) | 0.0556 (14) | 0.0558 (14) | 0.0019 (9) | −0.0016 (9) | 0.0104 (12) |
C61 | 0.0178 (11) | 0.0188 (12) | 0.0244 (13) | 0.0037 (9) | −0.0009 (9) | −0.0011 (10) |
C62 | 0.0168 (11) | 0.0222 (12) | 0.0240 (13) | 0.0031 (9) | 0.0000 (9) | −0.0011 (10) |
C63 | 0.0250 (13) | 0.0247 (13) | 0.0286 (14) | 0.0007 (10) | −0.0049 (10) | −0.0032 (11) |
C64 | 0.0348 (15) | 0.0321 (14) | 0.0198 (13) | 0.0065 (12) | −0.0033 (11) | −0.0026 (11) |
C65 | 0.0317 (14) | 0.0302 (14) | 0.0252 (14) | 0.0025 (11) | 0.0043 (11) | 0.0054 (11) |
C66 | 0.0256 (13) | 0.0211 (12) | 0.0268 (13) | 0.0008 (10) | 0.0031 (10) | 0.0006 (10) |
C67 | 0.0223 (13) | 0.0224 (12) | 0.0254 (13) | 0.0014 (10) | −0.0005 (10) | −0.0015 (10) |
O61 | 0.0218 (10) | 0.0699 (16) | 0.0307 (11) | −0.0123 (10) | 0.0018 (8) | −0.0169 (11) |
O62 | 0.0207 (9) | 0.0486 (12) | 0.0281 (10) | 0.0055 (8) | 0.0001 (8) | −0.0112 (9) |
C68 | 0.0208 (12) | 0.0238 (13) | 0.0266 (13) | −0.0007 (10) | 0.0008 (10) | −0.0028 (10) |
O63 | 0.0248 (9) | 0.0344 (11) | 0.0296 (10) | 0.0059 (8) | 0.0050 (8) | 0.0063 (8) |
O64 | 0.0181 (9) | 0.0556 (14) | 0.0436 (12) | −0.0006 (9) | 0.0027 (9) | 0.0092 (10) |
N11—C16 | 1.484 (4) | C36—H36B | 0.9900 |
N11—C12 | 1.493 (4) | C341—C346 | 1.389 (4) |
N11—H11 | 0.99 (4) | C341—C342 | 1.394 (4) |
N11—H12 | 0.79 (4) | C342—C343 | 1.390 (4) |
C12—C13 | 1.514 (4) | C342—H342 | 0.9500 |
C12—H12A | 0.9900 | C343—C344 | 1.378 (4) |
C12—H12B | 0.9900 | C343—H343 | 0.9500 |
C13—N14 | 1.462 (3) | C344—O344 | 1.380 (4) |
C13—H13A | 0.9900 | C344—C345 | 1.380 (5) |
C13—H13B | 0.9900 | C345—C346 | 1.374 (5) |
N14—C141 | 1.418 (3) | C345—H345 | 0.9500 |
N14—C15 | 1.456 (3) | C346—H346 | 0.9500 |
C15—C16 | 1.514 (4) | O344—C347 | 1.420 (4) |
C15—H15A | 0.9900 | C347—H37A | 0.9800 |
C15—H15B | 0.9900 | C347—H37B | 0.9800 |
C16—H16A | 0.9900 | C347—H37C | 0.9800 |
C16—H16B | 0.9900 | N41—C42 | 1.485 (4) |
C141—C146 | 1.385 (4) | N41—C46 | 1.493 (4) |
C141—C142 | 1.401 (4) | N41—H41 | 1.00 (4) |
C142—C143 | 1.378 (5) | N41—H42 | 0.91 (4) |
C142—H142 | 0.9500 | C42—C43 | 1.510 (4) |
C143—C144 | 1.393 (4) | C42—H42A | 0.9900 |
C143—H143 | 0.9500 | C42—H42B | 0.9900 |
C144—O144 | 1.376 (4) | C43—N44 | 1.451 (4) |
C144—C145 | 1.377 (4) | C43—H43A | 0.9900 |
C145—C146 | 1.397 (4) | C43—H43B | 0.9900 |
C145—H145 | 0.9500 | N44—C441 | 1.422 (4) |
C146—H146 | 0.9500 | N44—C45 | 1.465 (4) |
O144—C147 | 1.422 (4) | C45—C46 | 1.511 (5) |
C147—H17A | 0.9800 | C45—H45A | 0.9900 |
C147—H17B | 0.9800 | C45—H45B | 0.9900 |
C147—H17C | 0.9800 | C46—H46A | 0.9900 |
N21—C26 | 1.485 (4) | C46—H46B | 0.9900 |
N21—C22 | 1.493 (4) | C441—C442 | 1.383 (4) |
N21—H21 | 0.99 (4) | C441—C446 | 1.403 (4) |
N21—H22 | 1.01 (4) | C442—C443 | 1.404 (4) |
C22—C23 | 1.512 (4) | C442—H442 | 0.9500 |
C22—H22A | 0.9900 | C443—C444 | 1.381 (4) |
C22—H22B | 0.9900 | C443—H443 | 0.9500 |
C23—N24 | 1.463 (4) | C444—O447 | 1.375 (4) |
C23—H23A | 0.9900 | C444—C445 | 1.395 (5) |
C23—H23B | 0.9900 | C445—C446 | 1.376 (4) |
N24—C241 | 1.419 (3) | C445—H445 | 0.9500 |
N24—C25 | 1.453 (3) | C446—H446 | 0.9500 |
C25—C26 | 1.512 (4) | O447—C447 | 1.427 (4) |
C25—H25A | 0.9900 | C447—H47A | 0.9800 |
C25—H25B | 0.9900 | C447—H47B | 0.9800 |
C26—H26A | 0.9900 | C447—H47C | 0.9800 |
C26—H26B | 0.9900 | C51—C56 | 1.387 (4) |
C241—C242 | 1.391 (4) | C51—C52 | 1.400 (4) |
C241—C246 | 1.394 (4) | C51—C57 | 1.522 (3) |
C242—C243 | 1.381 (4) | C52—C53 | 1.396 (4) |
C242—H242 | 0.9500 | C52—C58 | 1.523 (4) |
C243—C244 | 1.395 (4) | C53—C54 | 1.389 (4) |
C243—H243 | 0.9500 | C53—H53 | 0.9500 |
C244—O244 | 1.374 (3) | C54—C55 | 1.384 (5) |
C244—C245 | 1.380 (4) | C54—H54 | 0.9500 |
C245—C246 | 1.398 (4) | C55—C56 | 1.389 (4) |
C245—H245 | 0.9500 | C55—H55 | 0.9500 |
C246—H246 | 0.9500 | C56—H56 | 0.9500 |
O244—C247 | 1.422 (4) | C57—O52 | 1.246 (3) |
C247—H27A | 0.9800 | C57—O51 | 1.250 (3) |
C247—H27B | 0.9800 | C58—O54 | 1.230 (3) |
C247—H27C | 0.9800 | C58—O53 | 1.267 (4) |
N31—C32 | 1.490 (4) | C61—C66 | 1.399 (4) |
N31—C36 | 1.491 (4) | C61—C62 | 1.400 (4) |
N31—H31 | 0.94 (4) | C61—C67 | 1.511 (4) |
N31—H32 | 0.92 (4) | C62—C63 | 1.388 (4) |
C32—C33 | 1.515 (4) | C62—C68 | 1.511 (4) |
C32—H32A | 0.9900 | C63—C64 | 1.380 (4) |
C32—H32B | 0.9900 | C63—H63 | 0.9500 |
C33—N34 | 1.463 (3) | C64—C65 | 1.388 (4) |
C33—H33A | 0.9900 | C64—H64 | 0.9500 |
C33—H33B | 0.9900 | C65—C66 | 1.393 (4) |
N34—C341 | 1.416 (3) | C65—H65 | 0.9500 |
N34—C35 | 1.468 (3) | C66—H66 | 0.9500 |
C35—C36 | 1.511 (4) | C67—O61 | 1.255 (3) |
C35—H35A | 0.9900 | C67—O62 | 1.255 (3) |
C35—H35B | 0.9900 | C68—O64 | 1.229 (3) |
C36—H36A | 0.9900 | C68—O63 | 1.281 (3) |
C16—N11—C12 | 111.8 (2) | N34—C35—H35B | 109.5 |
C16—N11—H11 | 111 (2) | C36—C35—H35B | 109.5 |
C12—N11—H11 | 110.2 (19) | H35A—C35—H35B | 108.1 |
C16—N11—H12 | 107 (3) | N31—C36—C35 | 110.2 (2) |
C12—N11—H12 | 113 (3) | N31—C36—H36A | 109.6 |
H11—N11—H12 | 104 (3) | C35—C36—H36A | 109.6 |
N11—C12—C13 | 110.8 (2) | N31—C36—H36B | 109.6 |
N11—C12—H12A | 109.5 | C35—C36—H36B | 109.6 |
C13—C12—H12A | 109.5 | H36A—C36—H36B | 108.1 |
N11—C12—H12B | 109.5 | C346—C341—C342 | 117.4 (3) |
C13—C12—H12B | 109.5 | C346—C341—N34 | 119.3 (2) |
H12A—C12—H12B | 108.1 | C342—C341—N34 | 123.3 (2) |
N14—C13—C12 | 110.6 (2) | C343—C342—C341 | 121.7 (3) |
N14—C13—H13A | 109.5 | C343—C342—H342 | 119.1 |
C12—C13—H13A | 109.5 | C341—C342—H342 | 119.1 |
N14—C13—H13B | 109.5 | C344—C343—C342 | 119.6 (3) |
C12—C13—H13B | 109.5 | C344—C343—H343 | 120.2 |
H13A—C13—H13B | 108.1 | C342—C343—H343 | 120.2 |
C141—N14—C15 | 116.9 (2) | C343—C344—O344 | 123.8 (3) |
C141—N14—C13 | 114.9 (2) | C343—C344—C345 | 119.0 (3) |
C15—N14—C13 | 110.1 (2) | O344—C344—C345 | 117.1 (3) |
N14—C15—C16 | 108.6 (2) | C346—C345—C344 | 121.4 (3) |
N14—C15—H15A | 110.0 | C346—C345—H345 | 119.3 |
C16—C15—H15A | 110.0 | C344—C345—H345 | 119.3 |
N14—C15—H15B | 110.0 | C345—C346—C341 | 120.8 (3) |
C16—C15—H15B | 110.0 | C345—C346—H346 | 119.6 |
H15A—C15—H15B | 108.4 | C341—C346—H346 | 119.6 |
N11—C16—C15 | 110.8 (2) | C344—O344—C347 | 116.8 (2) |
N11—C16—H16A | 109.5 | O344—C347—H37A | 109.5 |
C15—C16—H16A | 109.5 | O344—C347—H37B | 109.5 |
N11—C16—H16B | 109.5 | H37A—C347—H37B | 109.5 |
C15—C16—H16B | 109.5 | O344—C347—H37C | 109.5 |
H16A—C16—H16B | 108.1 | H37A—C347—H37C | 109.5 |
C146—C141—C142 | 117.7 (2) | H37B—C347—H37C | 109.5 |
C146—C141—N14 | 124.4 (2) | C42—N41—C46 | 111.7 (2) |
C142—C141—N14 | 117.8 (2) | C42—N41—H41 | 105 (2) |
C143—C142—C141 | 120.8 (3) | C46—N41—H41 | 110 (2) |
C143—C142—H142 | 119.6 | C42—N41—H42 | 109 (2) |
C141—C142—H142 | 119.6 | C46—N41—H42 | 111 (2) |
C142—C143—C144 | 121.0 (3) | H41—N41—H42 | 109 (3) |
C142—C143—H143 | 119.5 | N41—C42—C43 | 111.4 (2) |
C144—C143—H143 | 119.5 | N41—C42—H42A | 109.3 |
O144—C144—C145 | 125.3 (3) | C43—C42—H42A | 109.3 |
O144—C144—C143 | 115.8 (3) | N41—C42—H42B | 109.3 |
C145—C144—C143 | 118.8 (3) | C43—C42—H42B | 109.3 |
C144—C145—C146 | 120.2 (3) | H42A—C42—H42B | 108.0 |
C144—C145—H145 | 119.9 | N44—C43—C42 | 110.2 (2) |
C146—C145—H145 | 119.9 | N44—C43—H43A | 109.6 |
C141—C146—C145 | 121.5 (3) | C42—C43—H43A | 109.6 |
C141—C146—H146 | 119.3 | N44—C43—H43B | 109.6 |
C145—C146—H146 | 119.3 | C42—C43—H43B | 109.6 |
C144—O144—C147 | 116.4 (2) | H43A—C43—H43B | 108.1 |
O144—C147—H17A | 109.5 | C441—N44—C43 | 117.1 (2) |
O144—C147—H17B | 109.5 | C441—N44—C45 | 116.1 (2) |
H17A—C147—H17B | 109.5 | C43—N44—C45 | 110.1 (2) |
O144—C147—H17C | 109.5 | N44—C45—C46 | 110.4 (2) |
H17A—C147—H17C | 109.5 | N44—C45—H45A | 109.6 |
H17B—C147—H17C | 109.5 | C46—C45—H45A | 109.6 |
C26—N21—C22 | 111.6 (2) | N44—C45—H45B | 109.6 |
C26—N21—H21 | 112 (2) | C46—C45—H45B | 109.6 |
C22—N21—H21 | 111 (2) | H45A—C45—H45B | 108.1 |
C26—N21—H22 | 107 (2) | N41—C46—C45 | 110.8 (2) |
C22—N21—H22 | 111 (2) | N41—C46—H46A | 109.5 |
H21—N21—H22 | 104 (3) | C45—C46—H46A | 109.5 |
N21—C22—C23 | 111.0 (2) | N41—C46—H46B | 109.5 |
N21—C22—H22A | 109.4 | C45—C46—H46B | 109.5 |
C23—C22—H22A | 109.4 | H46A—C46—H46B | 108.1 |
N21—C22—H22B | 109.4 | C442—C441—C446 | 117.2 (3) |
C23—C22—H22B | 109.4 | C442—C441—N44 | 123.8 (3) |
H22A—C22—H22B | 108.0 | C446—C441—N44 | 118.8 (3) |
N24—C23—C22 | 110.7 (2) | C441—C442—C443 | 121.7 (3) |
N24—C23—H23A | 109.5 | C441—C442—H442 | 119.1 |
C22—C23—H23A | 109.5 | C443—C442—H442 | 119.1 |
N24—C23—H23B | 109.5 | C444—C443—C442 | 119.9 (3) |
C22—C23—H23B | 109.5 | C444—C443—H443 | 120.0 |
H23A—C23—H23B | 108.1 | C442—C443—H443 | 120.0 |
C241—N24—C25 | 117.6 (2) | O447—C444—C443 | 125.8 (3) |
C241—N24—C23 | 115.1 (2) | O447—C444—C445 | 115.4 (3) |
C25—N24—C23 | 110.0 (2) | C443—C444—C445 | 118.9 (3) |
N24—C25—C26 | 108.7 (2) | C446—C445—C444 | 120.6 (3) |
N24—C25—H25A | 109.9 | C446—C445—H445 | 119.7 |
C26—C25—H25A | 109.9 | C444—C445—H445 | 119.7 |
N24—C25—H25B | 109.9 | C445—C446—C441 | 121.5 (3) |
C26—C25—H25B | 109.9 | C445—C446—H446 | 119.2 |
H25A—C25—H25B | 108.3 | C441—C446—H446 | 119.2 |
N21—C26—C25 | 110.4 (2) | C444—O447—C447 | 117.0 (2) |
N21—C26—H26A | 109.6 | O447—C447—H47A | 109.5 |
C25—C26—H26A | 109.6 | O447—C447—H47B | 109.5 |
N21—C26—H26B | 109.6 | H47A—C447—H47B | 109.5 |
C25—C26—H26B | 109.6 | O447—C447—H47C | 109.5 |
H26A—C26—H26B | 108.1 | H47A—C447—H47C | 109.5 |
C242—C241—C246 | 117.6 (2) | H47B—C447—H47C | 109.5 |
C242—C241—N24 | 118.2 (2) | C56—C51—C52 | 119.4 (2) |
C246—C241—N24 | 124.1 (2) | C56—C51—C57 | 119.0 (2) |
C243—C242—C241 | 121.5 (3) | C52—C51—C57 | 121.6 (2) |
C243—C242—H242 | 119.2 | C53—C52—C51 | 119.0 (3) |
C241—C242—H242 | 119.2 | C53—C52—C58 | 117.6 (2) |
C242—C243—C244 | 120.4 (3) | C51—C52—C58 | 123.2 (2) |
C242—C243—H243 | 119.8 | C54—C53—C52 | 121.0 (3) |
C244—C243—H243 | 119.8 | C54—C53—H53 | 119.5 |
O244—C244—C245 | 125.0 (3) | C52—C53—H53 | 119.5 |
O244—C244—C243 | 115.9 (3) | C55—C54—C53 | 119.7 (3) |
C245—C244—C243 | 119.1 (3) | C55—C54—H54 | 120.1 |
C244—C245—C246 | 120.1 (3) | C53—C54—H54 | 120.1 |
C244—C245—H245 | 120.0 | C54—C55—C56 | 119.6 (3) |
C246—C245—H245 | 120.0 | C54—C55—H55 | 120.2 |
C241—C246—C245 | 121.3 (3) | C56—C55—H55 | 120.2 |
C241—C246—H246 | 119.4 | C51—C56—C55 | 121.2 (3) |
C245—C246—H246 | 119.4 | C51—C56—H56 | 119.4 |
C244—O244—C247 | 117.3 (3) | C55—C56—H56 | 119.4 |
O244—C247—H27A | 109.5 | O52—C57—O51 | 124.9 (2) |
O244—C247—H27B | 109.5 | O52—C57—C51 | 118.0 (2) |
H27A—C247—H27B | 109.5 | O51—C57—C51 | 117.1 (2) |
O244—C247—H27C | 109.5 | O54—C58—O53 | 125.9 (3) |
H27A—C247—H27C | 109.5 | O54—C58—C52 | 119.1 (3) |
H27B—C247—H27C | 109.5 | O53—C58—C52 | 114.8 (2) |
C32—N31—C36 | 111.5 (2) | C66—C61—C62 | 119.1 (2) |
C32—N31—H31 | 104 (2) | C66—C61—C67 | 118.8 (2) |
C36—N31—H31 | 111 (2) | C62—C61—C67 | 122.0 (2) |
C32—N31—H32 | 108 (2) | C63—C62—C61 | 119.5 (2) |
C36—N31—H32 | 113 (2) | C63—C62—C68 | 117.4 (2) |
H31—N31—H32 | 109 (3) | C61—C62—C68 | 122.8 (2) |
N31—C32—C33 | 111.2 (2) | C64—C63—C62 | 121.1 (3) |
N31—C32—H32A | 109.4 | C64—C63—H63 | 119.4 |
C33—C32—H32A | 109.4 | C62—C63—H63 | 119.4 |
N31—C32—H32B | 109.4 | C63—C64—C65 | 119.9 (3) |
C33—C32—H32B | 109.4 | C63—C64—H64 | 120.0 |
H32A—C32—H32B | 108.0 | C65—C64—H64 | 120.0 |
N34—C33—C32 | 110.0 (2) | C64—C65—C66 | 119.6 (3) |
N34—C33—H33A | 109.7 | C64—C65—H65 | 120.2 |
C32—C33—H33A | 109.7 | C66—C65—H65 | 120.2 |
N34—C33—H33B | 109.7 | C65—C66—C61 | 120.7 (3) |
C32—C33—H33B | 109.7 | C65—C66—H66 | 119.6 |
H33A—C33—H33B | 108.2 | C61—C66—H66 | 119.6 |
C341—N34—C33 | 116.0 (2) | O61—C67—O62 | 124.1 (2) |
C341—N34—C35 | 114.7 (2) | O61—C67—C61 | 117.8 (2) |
C33—N34—C35 | 110.1 (2) | O62—C67—C61 | 118.2 (2) |
N34—C35—C36 | 110.7 (2) | O64—C68—O63 | 124.7 (3) |
N34—C35—H35A | 109.5 | O64—C68—C62 | 120.2 (2) |
C36—C35—H35A | 109.5 | O63—C68—C62 | 114.9 (2) |
C16—N11—C12—C13 | −51.3 (3) | C344—C345—C346—C341 | −1.1 (5) |
N11—C12—C13—N14 | 54.6 (3) | C342—C341—C346—C345 | −0.3 (5) |
C12—C13—N14—C141 | 164.1 (2) | N34—C341—C346—C345 | 177.6 (3) |
C12—C13—N14—C15 | −61.4 (3) | C343—C344—O344—C347 | −44.2 (5) |
C141—N14—C15—C16 | −163.5 (2) | C345—C344—O344—C347 | 139.9 (3) |
C13—N14—C15—C16 | 63.1 (3) | C46—N41—C42—C43 | −52.1 (3) |
C12—N11—C16—C15 | 54.0 (3) | N41—C42—C43—N44 | 56.6 (3) |
N14—C15—C16—N11 | −59.3 (3) | C42—C43—N44—C441 | 163.5 (2) |
C15—N14—C141—C146 | −12.7 (4) | C42—C43—N44—C45 | −61.0 (3) |
C13—N14—C141—C146 | 118.6 (3) | C441—N44—C45—C46 | −162.8 (2) |
C15—N14—C141—C142 | 165.0 (2) | C43—N44—C45—C46 | 61.2 (3) |
C13—N14—C141—C142 | −63.7 (3) | C42—N41—C46—C45 | 51.8 (3) |
C146—C141—C142—C143 | 0.2 (4) | N44—C45—C46—N41 | −56.2 (3) |
N14—C141—C142—C143 | −177.6 (3) | C43—N44—C441—C442 | 6.8 (4) |
C141—C142—C143—C144 | 0.5 (5) | C45—N44—C441—C442 | −126.0 (3) |
C142—C143—C144—O144 | 179.6 (3) | C43—N44—C441—C446 | −168.4 (3) |
C142—C143—C144—C145 | −0.6 (5) | C45—N44—C441—C446 | 58.7 (3) |
O144—C144—C145—C146 | 179.7 (3) | C446—C441—C442—C443 | 3.4 (4) |
C143—C144—C145—C146 | 0.0 (4) | N44—C441—C442—C443 | −171.9 (3) |
C142—C141—C146—C145 | −0.9 (4) | C441—C442—C443—C444 | −1.1 (4) |
N14—C141—C146—C145 | 176.8 (2) | C442—C443—C444—O447 | 177.8 (3) |
C144—C145—C146—C141 | 0.7 (4) | C442—C443—C444—C445 | −2.1 (4) |
C145—C144—O144—C147 | 10.7 (4) | O447—C444—C445—C446 | −177.1 (3) |
C143—C144—O144—C147 | −169.6 (3) | C443—C444—C445—C446 | 2.8 (5) |
C26—N21—C22—C23 | −51.3 (3) | C444—C445—C446—C441 | −0.4 (5) |
N21—C22—C23—N24 | 54.2 (3) | C442—C441—C446—C445 | −2.7 (4) |
C22—C23—N24—C241 | 163.3 (2) | N44—C441—C446—C445 | 172.9 (3) |
C22—C23—N24—C25 | −61.0 (3) | C443—C444—O447—C447 | 0.5 (4) |
C241—N24—C25—C26 | −162.1 (2) | C445—C444—O447—C447 | −179.6 (3) |
C23—N24—C25—C26 | 63.4 (3) | C56—C51—C52—C53 | −2.0 (4) |
C22—N21—C26—C25 | 54.4 (3) | C57—C51—C52—C53 | 174.2 (2) |
N24—C25—C26—N21 | −60.0 (3) | C56—C51—C52—C58 | 172.7 (2) |
C25—N24—C241—C242 | 164.0 (3) | C57—C51—C52—C58 | −11.1 (4) |
C23—N24—C241—C242 | −63.8 (3) | C51—C52—C53—C54 | 0.8 (4) |
C25—N24—C241—C246 | −12.4 (4) | C58—C52—C53—C54 | −174.2 (3) |
C23—N24—C241—C246 | 119.8 (3) | C52—C53—C54—C55 | 0.9 (4) |
C246—C241—C242—C243 | 0.0 (4) | C53—C54—C55—C56 | −1.3 (5) |
N24—C241—C242—C243 | −176.6 (3) | C52—C51—C56—C55 | 1.6 (4) |
C241—C242—C243—C244 | 0.2 (5) | C57—C51—C56—C55 | −174.8 (3) |
C242—C243—C244—O244 | 179.8 (3) | C54—C55—C56—C51 | 0.1 (4) |
C242—C243—C244—C245 | 0.0 (5) | C56—C51—C57—O52 | 141.7 (3) |
O244—C244—C245—C246 | 179.9 (3) | C52—C51—C57—O52 | −34.5 (4) |
C243—C244—C245—C246 | −0.3 (4) | C56—C51—C57—O51 | −36.7 (4) |
C242—C241—C246—C245 | −0.3 (4) | C52—C51—C57—O51 | 147.0 (3) |
N24—C241—C246—C245 | 176.0 (3) | C53—C52—C58—O54 | −60.9 (4) |
C244—C245—C246—C241 | 0.5 (4) | C51—C52—C58—O54 | 124.3 (3) |
C245—C244—O244—C247 | 2.9 (4) | C53—C52—C58—O53 | 114.5 (3) |
C243—C244—O244—C247 | −176.9 (3) | C51—C52—C58—O53 | −60.2 (3) |
C36—N31—C32—C33 | −53.7 (3) | C66—C61—C62—C63 | −2.0 (4) |
N31—C32—C33—N34 | 56.5 (3) | C67—C61—C62—C63 | 174.2 (2) |
C32—C33—N34—C341 | 167.6 (2) | C66—C61—C62—C68 | 171.6 (2) |
C32—C33—N34—C35 | −60.0 (3) | C67—C61—C62—C68 | −12.3 (4) |
C341—N34—C35—C36 | −166.1 (2) | C61—C62—C63—C64 | 0.9 (4) |
C33—N34—C35—C36 | 60.9 (3) | C68—C62—C63—C64 | −173.0 (2) |
C32—N31—C36—C35 | 53.6 (3) | C62—C63—C64—C65 | 0.5 (4) |
N34—C35—C36—N31 | −57.2 (3) | C63—C64—C65—C66 | −0.8 (4) |
C33—N34—C341—C346 | −173.4 (3) | C64—C65—C66—C61 | −0.4 (4) |
C35—N34—C341—C346 | 56.4 (3) | C62—C61—C66—C65 | 1.7 (4) |
C33—N34—C341—C342 | 4.3 (4) | C67—C61—C66—C65 | −174.6 (2) |
C35—N34—C341—C342 | −125.9 (3) | C66—C61—C67—O61 | −34.9 (4) |
C346—C341—C342—C343 | 1.6 (4) | C62—C61—C67—O61 | 149.0 (3) |
N34—C341—C342—C343 | −176.1 (3) | C66—C61—C67—O62 | 144.0 (3) |
C341—C342—C343—C344 | −1.6 (5) | C62—C61—C67—O62 | −32.2 (4) |
C342—C343—C344—O344 | −175.6 (3) | C63—C62—C68—O64 | −64.0 (3) |
C342—C343—C344—C345 | 0.2 (5) | C61—C62—C68—O64 | 122.3 (3) |
C343—C344—C345—C346 | 1.2 (5) | C63—C62—C68—O63 | 112.2 (3) |
O344—C344—C345—C346 | 177.3 (3) | C61—C62—C68—O63 | −61.4 (3) |
Cg3 and Cg4 represent the centroids of the C61–C66 and C51–C56 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O51 | 0.99 (4) | 1.73 (4) | 2.714 (4) | 175 (2) |
N11—H12···O63i | 0.80 (4) | 2.03 (4) | 2.738 (3) | 148 (3) |
N21—H21···O61 | 0.99 (4) | 1.72 (4) | 2.707 (4) | 177 (3) |
N21—H22···O53ii | 1.01 (4) | 1.88 (4) | 2.744 (3) | 142 (3) |
N31—H31···O63iii | 0.94 (3) | 1.77 (3) | 2.685 (3) | 163 (3) |
N31—H32···O52 | 0.92 (4) | 1.83 (4) | 2.732 (3) | 164 (3) |
N41—H41···O53iv | 1.00 (4) | 1.74 (4) | 2.711 (3) | 163 (3) |
N41—H42···O62 | 0.90 (4) | 1.89 (4) | 2.740 (3) | 157 (3) |
C36—H36A···O51v | 0.99 | 2.40 | 3.354 (4) | 160 |
C46—H46A···O61v | 0.99 | 2.42 | 3.359 (4) | 158 |
C13—H13B···Cg3i | 0.99 | 2.84 | 3.795 (3) | 161 |
C23—H23B···Cg4i | 0.99 | 2.85 | 3.800 (3) | 162 |
Symmetry codes: (i) −x+3/2, y+1/2, z−1/2; (ii) −x+3/2, y−1/2, z+1/2; (iii) −x+1, −y+1, z−1/2; (iv) −x+1, −y+2, z+1/2; (v) x−1/2, −y+3/2, z. |
Acknowledgements
HJS is grateful to the University of Mysore for research facilities.
Funding information
HSY thanks UGC for a BSR Faculty fellowship for three years.
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