research communications
Syntheses, crystal structures and Hirshfeld surface analysis of three salts of 1-(4-nitrophenyl)piperazine
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570 006, India, bInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287 Darmstadt, Germany, cThomas Jefferson High School for Science and Technology, 6560 Braddock Rd, Alexandria VA 22312, USA, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington DC 20059, USA
*Correspondence e-mail: yathirajan@hotmail.com
The structures and Hirshfeld surface analysis of three salts of 1-(4-nitrophenyl)piperazine are discussed. In 4-(4-nitrophenyl)piperazin-1-ium salicylate (C10H14N3O2+·C7H5O3−), there are strong hydrogen bonds between cation and anion and the 4-nitrophenyl substituent occupies an equatorial position in the piperazinium ring. The cation and anion are linked together by supramolecular interactions [graph-set notation of hydrogen bonding (6) propagating in the a-axis direction]. Additionally, there is π–π stacking involving the salicylate anion and the piperazinium cation in adjacent asymmetric units as well as a C—H⋯π interaction between a hydrogen atom on the piperazine ring and the phenyl ring within the salicyclate anion. In bis[4-(4-nitrophenyl)piperazin-1-ium] bis(4-fluorobenzoate) trihydrate (2C10H14N3O2+·2C7H4FO2−·3H2O), there are two cations, two anions, and three water molecules of solvation in the all linked by hydrogen bonds [graph-set notation of hydrogen bonding R22(20) between adjacent cations and R33(9) between a cation and its adjacent anion]. In the anion, the 4-nitrophenyl ring occupies an axial substitution position in the piperazinium ring, which is relatively rare. Within the the phenyl groups in the cations show an offset π–π interaction. Additionally, there is a C—H⋯π interaction between a hydrogen atom on the phenyl ring within a cation and the phenyl ring within an anion. In 4-(4-nitrophenyl)piperazin-1-ium 3,5-dinitrobenzoate (C10H14N3O2+·C7H4N2O6−), there is a strong N—H⋯O hydrogen bond linking the cation and anion and the 4-nitrophenyl ring occupies an axial substitution position in the piperazinium ring, as seen in the previous structure. In the crystal, the cation and the anion form a complex three-dimensional hydrogen-bonded array involving R22(8), R44(12) and R44(20) rings propogating in the a-axis direction. The nitrophenyl group is disordered with occupancies of 0.806 (10) and 0.194 (10).
1. Chemical context
Piperazines and substituted piperazines are important pharmacophores that can be found in many biologically active compounds across a number of different therapeutic areas (Berkheij, 2005), being used as antifungal (Upadhayaya et al., 2004), anti-bacterial, anti-malarial and anti-psychotic agents (Chaudhary et al., 2006). An insight into advances on the antimicrobial activity of piperazine derivatives has been reported (Kharb et al., 2012).
Piperazines are among the most important building blocks in today's drug discovery and are found in biologically active compounds across a number of different therapeutic areas (Brockunier et al., 2004; Bogatcheva et al., 2006). A review of pharmacological and toxicological information for piperazine derivatives is given by Elliott (2011).
4-Nitrophenylpiperazinium chloride monohydrate has been used as an intermediate in the synthesis of anticancer drugs, transcriptase inhibitors and antifungal reagents and is also an important reagent for potassium channel openers, which show considerable biomolecular current-voltage rectification characteristics (Lu, 2007).
The inclusion behaviour of 4-sulfonatocalix[n]arenes (SCXn) (n = 4, 6, 8) with 1-(4-nitrophenyl)piperazine (NPP) has been investigated by UV spectroscopy and fluorescence spectroscopy at different pH values (Zhang et al., 2014). The design, synthesis and biological profiling of aryl piperazine-based scaffolds for the management of androgen-sensitive prostatic disorders has been published (Gupta et al., 2016). 4-Nitrophenylpiperazine was the starting material in the synthesis and biological evaluation of novel piperazine-containing hydrazone derivatives (Kaya et al., 2016). Several previous investigations in this area are outlined in the Database Survey section.
In view of the importance of piperazines in general, and the use of 4-nitrophenylpiperazine in particular, the present paper reports the viz., 4-nitrophenylpiperazinium salicylate (1), 4-nitrophenylpiperazinium 4-fluorobenzoate trihydrate (2) and 4-nitrophenylpiperazinium 3,5-dinitrobenzoate (3).
studies of three salts of 4-nitrophenylpiperazine,2. Structural commentary
Compound 1, (4-nitrophenylpiperazinium salicylate; C10H14N3O2·C7H5O3), crystallizes in the monoclinic P21/n with four molecules in the (Fig. 1). The structure contains a 4-phenylpiperazinium cation linked to a salicylate anion by an N—H⋯O hydrogen bond [H⋯O = 1.792 (15) Å; N⋯O = 2.6957 (18) Å; N—H⋯O = 174.0 (18)°, Table 1]. In the salicylate anion, there is an intramolecular hydrogen bond involving the phenol hydrogen and the carboxylate group [ S11(6) in graph-set notation (Etter et al., 1990): H⋯O = 1.733 (17) Å; O⋯O = 2.5221 (17) Å; O—H⋯O = 152 (2)°]. In the conformation of the cation and anion, the dihedral angles between the piperazine ring and the phenyl ring, the piperazine ring with the salicylate ring, the phenyl ring with the salicylate ring, the nitro group and the phenyl ring, and the salicylate ring and its carboxylate group are 36.83 (6), 28.65 (6), 55.01 (5), 1.8 (3) and 7.0 (2)°, respectively. The first dihedral angle of 36.83 (6)° is indicative of the fact that the 4-nitrophenyl ring occupies an equatorial position in the phenyl ring, with the nitrogen lone pair occupying an axial position (see Fig. 1).
Compound 2, (4-nitrophenylpiperazinium 4-fluorobenzoate; 2C10H14N3O2·2C7H4FO2·3H2O, crystallizes in the monoclinic P21/n with four formula units in the The structure consists of two 4-nitrophenylpiperazinium cations, two 4-fluorobenzoate anions and three water solvate molecules (see Fig. 2). Each cation is linked to a corresponding anion by a strong N—H⋯O hydrogen bond (Table 2). The water molecules are also involved in hydrogen bonding, which will be discussed in further detail in section 3. As shown by Fig. 2, the structure has been divided into four rings, with rings A and D representing the two 4-fluorobenzoate anions and rings C and D representing the two nitrophenylpiperazinium cations. Rings A and B are linked by a strong N—H⋯O hydrogen bond [H⋯O = 1.86 (2) Å; N⋯O = 2.739 (5) Å; N—H⋯O = 169 (4)°], as are rings C and D [H⋯O = 1.84 (2) Å; N⋯O = 2.733 (5)Å; N—H⋯O = 176 (4)°]. Additionally, ring B′s piperazine substituent forms a weak C—H⋯O interaction with an oxygen atom in ring C′s terminal nitro group [H⋯O = 2.53 Å; C⋯O = 3.437 (6) Å; C—H⋯O = 155°]. Ring C′s piperazine substituent forms a similar interaction with ring B′s terminal nitro group [H⋯O = 2.53 Å; C⋯O = 3.401 (6) Å; C—H⋯O = 149°]. In the conformation of rings A–D, the dihedral angles between the 4-nitrophenyl rings in rings B and C, the 4-nitrophenyl ring and nitro group in ring B, the 4-nitrophenyl ring and nitro group in ring C, the piperazine ring and the 4-nitrophenyl ring in ring B, the piperazine ring and 4-nitrophenyl ring in ring C, the fluorobenzene ring in ring D and the phenyl ring in ring C, and the fluorobenzene ring in A and the phenyl ring in C are 11.4 (4), 1.1 (2), 0.2 (2), 141.72 (16), 145.17 (17), 101.47 (17) and 103.32 (17)°, respectively. The third and fourth angles listed indicate that the 4-nitrophenyl ring occupies an axial position in both cations, which is relatively rare. In a previous paper containing eleven analogous structures, only one had this substitution pattern (Archana et al., 2022).
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Compound 3, (4-nitrophenylpiperazinium 3,5-dinitrobenzoate; C10H14N3O2·C7H4N2O6), crystallizes in the monoclinic C2/c with eight formula units in the The structure consists of a 4-nitrophenylpiperazinium cation and a 3,5-dinitrobenzoate anion linked by a strong N—H⋯O hydrogen bond [H⋯O = 1.77 (2) Å; N⋯O = 2.705 (3) Å; N—H⋯O = 170.7 (17)°, Table 3] as shown in Fig. 3. The nitrophenyl ring is disordered with occupancies of 0.806 (10)/0.194 (10). In the cation, the dihedral angles between the piperazine ring and the major component of the 4-nitrophenyl ring, and the phenyl ring and its attached nitro group are 62.4 (1) and 10.1 (7)°, respectively. The former angle is indicative of the fact that the 4-nitrophenyl ring occupies an axial position, as it also did in 2. In the anion, the dihedral angle between the 3,5-dinitrobenzoate phenyl ring and its carboxylate substituent is 18.7 (1)°.
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3. Supramolecular features
In discussing the supramolecular features of the three structures, the direct hydrogen bonding involving the linking of the 4-nitrophenylpiperazinium cations and organic acid anions is omitted since it has already been discussed in the previous section. For 1, there is a zigzag chain of hydrogen bonds [graph-set notation (6) (Etter et al., 1990)], propagating in the b-axis direction involving the piperazinium cations and salicylate anions, as shown in Fig. 4. These are also illustrated in the Hirshfeld fingerprint plot (Spackman et al., 2021), which shows the prominent spikes involving both types of N—H⋯O hydrogen bonding (see Fig. 5). In the packing of the piperazinium cation and the salicylate anion, the salicylate anion forms a π–π interaction with the phenyl ring of a piperazinium cation [Cg2⋯Cg3i distance = 3.9296 (2) Å; symmetry code: (i) − x, y − , − z; slippage:1.505 Å; Cg2 and Cg3 are the centroids of the C1–C6 and C11–C16 rings, respectively]. Additionally, there is a C—H⋯π interaction between a hydrogen atom in the piperazine ring and the phenyl ring within the salicyclate anion (H⋯Cgii distance, 2.76 Å; C8—H8B⋯Cg2ii angle of 156°, symmetry code: (ii) − x, + y, − z).
For 2, there are two anions and two cations as well as three water molecules of solvation in the This leads to a complex three-dimensional array of hydrogen bonding involving both R22(20) motifs between rings B and C, and R33(9) motifs between rings C and D as well as one water molecule, as seen in Fig. 6. There are also C—H⋯F interactions between adjacent fluorobenzoate anions linking them into centrosymmetric dimers (symmetry code: + x, − y, − + z; see Table 2 for numerical details). These interactions are shown clearly as spikes in the fingerprint plots delineated into C—H⋯F and N—H⋯O interactions (Figs. 7 and 8, respectively). In the crystal, the phenyl ring in B forms an offset π–π interaction with the phenyl ring in C [Cg2⋯Cg4 distance, 3.8568 (7) Å; slippage of 1.835 Å; perpendicular distance of 3.454 (2) Å; Cg2 and Cg4 are the centroids of the C1B–C6B and C1C–C6C rings, respectively]. Additionally, there is a C–H⋯π interaction between a hydrogen atom on the phenyl ring in C and the phenyl ring in D [H6C⋯Cg6i, 2.91; C6—H6C⋯Cg6i angle of 161°, symmetry code: (i) 1 − x, 1 − y, −z; Cg6 is the centroid of the C11D–C16D ring].
For 3, the cation and the anion form a complex three-dimensional array of hydrogen bonding involving R22(8), R44(12) and R44(20) rings propogating in the a-axis direction between the 4-nitrophenyl group of one cation with the piperazinium ring of an adjacent cation (symmetry code: − x, − y, 1 − z), two cations and two anions in adjacent asymmetric units (−x, −y, 1 − z), two cations and two anions in adjacent asymmetric units (symmetry code: − − x, + y, − z), respectively, as seen in Fig. 9 (Table 3). These show as sharp spikes in the fingerprint plot showing the N—H⋯O interactions (Fig. 10). Additionally, the nitrobenzene group within the piperazinium cation forms a π–π interaction with the phenyl group of another piperazinium cation in an adjacent [Cg2⋯Cg2i distance, 4.4132 (9) Å; perpendicular distance: 3.5596 (9) Å; slippage of 2.609 Å, symmetry code: (i) − x, − y, 1 − z; Cg2 is the centroid of the C1–C6D ring].
4. Database survey
Related structures containing 1-phenylpiperazine or the 1-phenylpiperazinium cation include racemic perhydrotriphenylene (PHTP), which has been shown to form a polar et al., 1997). The of the simple salt 4-nitrophenylpiperazinium chloride monohydrate has been reported (LIJNAU; Lu, 2007). The of 4,6-dimethoxypyrimidin-2-amine-1-(4-nitrophenyl)piperazine (1:1) has been published (LUDMUU; Wang et al., 2014) as well as the synthesis and of a Schiff base, 5-methyl-2-{[4-(4-nitrophenyl)piperazin-1-yl]methyl}phenol (WUWBIC; Ayeni et al., 2019).
with 1-(4-nitrophenyl)piperazine (NPP) as a guest molecule (CSD refcode NOVWOK; KönigNMR-based investigations of acyl-functionalized piperazines concerning their conformational behavior in solution has been studied and crystal structures of 1-(4-fluorobenzoyl)-4-(4-nitrophenyl)piperazine (BIQYIM), 1-(4-bromobenzoyl)-4-(4-nitrophenyl)piperazine (BIRHES), 1-(3-bromobenzoyl)-4-(4-nitrophenyl)piperazine (BIRHIW) and (piperazine-1,4-diyl)bis[(4-fluorophenyl)methanone] (BIRGOB) have been reported (Wodtke et al., 2018). We have recently reported the crystal structures of some salts of 4-methoxyphenylpiperazine (Kiran Kumar et al., 2019) and also 2-methoxyphenylpiperazine (Harish Chinthal et al., 2020). We have recently reported the crystal structures of some salts of piperazine derivatives (Archana et al., 2021). Very recently, we have reported the crystal structures of six salts of 4-nitrophenylpiperazine (NEBVOJ; NEBVUP; NEBWAW; NEBWEA; NEBWIE; NEBWOK) and four salts of 1-phenylpiperazine (Mahesha et al., 2022a, 2022b). The syntheses and crystal structures of 4-(4-nitrophenyl)piperazin-1-ium benzoate monohydrate (BEFGIG) and 4-(4-nitrophenyl)piperazin-1-ium 2-carboxy-4,6-dinitrophenolate (BEFGOM) have been reported (Shankara Prasad et al., 2022).
5. Synthesis and crystallization
For the synthesis of salts 1–3, a solution of commercially available (from Sigma-Aldrich) 4-nitrophenylpiperazine (100 mg, 0.483 mol) in methanol (10 ml) was mixed with equimolar solutions of the appropriate acids in methanol (10 ml) and ethyl acetate (10 ml) viz., salicylic acid (67 mg) for 1, 4-fluorobenzoic acid (68 mg) for 2 and 3,5-dinitrobenzoic acid (102 mg) for 3 (see Fig. 11 for reaction scheme). The corresponding solutions were stirred for 15 minutes at room temperature and allowed to stand at the same temperature. X-ray quality crystals were formed on slow evaporation (for 1 and 2) for a week. For 3, DMF (3 ml) was used for crystallization. The corresponding melting points were 453–458 K (1), 373–378 K (2) and 445–447 K (3).
6. Refinement
Crystal data, data collection and structure . In all structures, a riding model was used for the H atoms attached to C with Uiso(H) = 1.2Ueq(C) while the N–H and water O–H hydrogen atoms were refined isotropically. In 3 the nitrophenyl group is disordered with occupancies of 0.806 (10)/0.194 (10) and constrained to have similar metrical parameters.
details for the three structures are summarized in Table 4
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Supporting information
https://doi.org/10.1107/S2056989023002517/vm2276sup1.cif
contains datablocks 1, 2, 3. DOI:Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989023002517/vm22761sup2.hkl
Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989023002517/vm22762sup3.hkl
Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S2056989023002517/vm22763sup4.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023002517/vm22761sup5.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989023002517/vm22762sup6.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989023002517/vm22763sup7.cml
For all structures, data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C10H14N3O2+·C7H5O3− | F(000) = 728 |
Mr = 345.35 | Dx = 1.405 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0018 (3) Å | Cell parameters from 3505 reflections |
b = 7.3938 (3) Å | θ = 2.6–27.7° |
c = 31.531 (1) Å | µ = 0.11 mm−1 |
β = 90.132 (4)° | T = 293 K |
V = 1632.35 (11) Å3 | Prism, yellow |
Z = 4 | 0.48 × 0.40 × 0.40 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 2606 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.016 |
Rotation method data acquisition using ω scans. | θmax = 27.8°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −8→7 |
Tmin = 0.886, Tmax = 1.000 | k = −5→9 |
6955 measured reflections | l = −30→41 |
3506 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: mixed |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0464P)2 + 0.6706P] where P = (Fo2 + 2Fc2)/3 |
3506 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.22 e Å−3 |
3 restraints | Δρmin = −0.21 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 | ||
C1 | 0.9480 (2) | 0.4305 (2) | 0.40335 (5) | 0.0322 (4) | |
C2 | 1.1448 (3) | 0.4516 (3) | 0.40783 (6) | 0.0420 (4) | |
H2 | 1.214403 | 0.506875 | 0.386354 | 0.050* | |
C3 | 1.2372 (3) | 0.3912 (3) | 0.44378 (6) | 0.0481 (5) | |
H3 | 1.368446 | 0.406601 | 0.446657 | 0.058* | |
C4 | 1.1344 (3) | 0.3082 (3) | 0.47539 (5) | 0.0410 (4) | |
C5 | 0.9401 (3) | 0.2866 (3) | 0.47224 (6) | 0.0435 (4) | |
H5 | 0.871988 | 0.231148 | 0.493930 | 0.052* | |
C6 | 0.8476 (3) | 0.3485 (3) | 0.43645 (6) | 0.0416 (4) | |
H6 | 0.715817 | 0.335531 | 0.434273 | 0.050* | |
C7 | 0.6915 (2) | 0.6105 (3) | 0.37246 (5) | 0.0376 (4) | |
H7A | 0.742612 | 0.729932 | 0.378242 | 0.045* | |
H7B | 0.616032 | 0.573640 | 0.396727 | 0.045* | |
C8 | 0.5651 (2) | 0.6186 (3) | 0.33363 (5) | 0.0380 (4) | |
H8A | 0.499976 | 0.503859 | 0.330013 | 0.046* | |
H8B | 0.469135 | 0.711902 | 0.337361 | 0.046* | |
C9 | 0.8353 (3) | 0.5226 (3) | 0.29013 (5) | 0.0423 (4) | |
H9A | 0.909732 | 0.550803 | 0.265077 | 0.051* | |
H9B | 0.780236 | 0.403244 | 0.286470 | 0.051* | |
C10 | 0.9632 (2) | 0.5244 (3) | 0.32892 (5) | 0.0371 (4) | |
H10A | 1.064043 | 0.435557 | 0.325689 | 0.045* | |
H10B | 1.021744 | 0.642570 | 0.332035 | 0.045* | |
C11 | 0.3106 (2) | 0.5498 (2) | 0.16617 (5) | 0.0327 (4) | |
C12 | 0.1281 (2) | 0.6228 (2) | 0.17173 (5) | 0.0322 (4) | |
C13 | −0.0084 (3) | 0.6071 (3) | 0.13974 (6) | 0.0407 (4) | |
H13 | −0.130219 | 0.654106 | 0.143688 | 0.049* | |
C14 | 0.0370 (3) | 0.5219 (3) | 0.10231 (6) | 0.0462 (5) | |
H14 | −0.055100 | 0.510333 | 0.081179 | 0.055* | |
C15 | 0.2181 (3) | 0.4534 (3) | 0.09584 (6) | 0.0500 (5) | |
H15 | 0.248883 | 0.397864 | 0.070291 | 0.060* | |
C16 | 0.3527 (3) | 0.4681 (3) | 0.12755 (6) | 0.0434 (5) | |
H16 | 0.474660 | 0.422323 | 0.123046 | 0.052* | |
C17 | 0.4577 (2) | 0.5577 (2) | 0.20097 (6) | 0.0383 (4) | |
N1 | 0.84988 (19) | 0.4826 (2) | 0.36656 (4) | 0.0346 (3) | |
N2 | 0.6802 (2) | 0.6586 (2) | 0.29534 (5) | 0.0402 (4) | |
H21 | 0.735 (3) | 0.771 (2) | 0.2977 (6) | 0.048* | |
H22 | 0.597 (2) | 0.659 (3) | 0.2733 (5) | 0.048* | |
N3 | 1.2348 (3) | 0.2403 (3) | 0.51271 (6) | 0.0578 (5) | |
O1 | 1.1425 (3) | 0.1642 (3) | 0.54024 (5) | 0.0781 (5) | |
O2 | 1.4076 (3) | 0.2658 (3) | 0.51533 (6) | 0.0970 (7) | |
O3 | 0.61169 (19) | 0.4778 (2) | 0.19676 (5) | 0.0570 (4) | |
O4 | 0.41348 (19) | 0.6511 (2) | 0.23358 (4) | 0.0500 (4) | |
O5 | 0.07825 (18) | 0.7116 (2) | 0.20780 (4) | 0.0468 (3) | |
H5O | 0.178 (2) | 0.710 (3) | 0.2234 (6) | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0357 (9) | 0.0313 (9) | 0.0295 (8) | 0.0005 (7) | −0.0032 (7) | −0.0013 (7) |
C2 | 0.0369 (9) | 0.0525 (11) | 0.0367 (9) | 0.0005 (8) | −0.0012 (7) | 0.0080 (8) |
C3 | 0.0357 (9) | 0.0647 (13) | 0.0439 (11) | 0.0055 (9) | −0.0085 (8) | 0.0037 (10) |
C4 | 0.0503 (11) | 0.0412 (10) | 0.0315 (9) | 0.0072 (9) | −0.0107 (8) | 0.0010 (8) |
C5 | 0.0532 (11) | 0.0445 (11) | 0.0329 (9) | −0.0067 (9) | −0.0016 (8) | 0.0052 (8) |
C6 | 0.0366 (9) | 0.0507 (11) | 0.0374 (9) | −0.0081 (8) | −0.0053 (7) | 0.0048 (8) |
C7 | 0.0338 (9) | 0.0470 (11) | 0.0320 (9) | 0.0031 (8) | −0.0028 (7) | −0.0005 (8) |
C8 | 0.0354 (9) | 0.0405 (10) | 0.0382 (9) | −0.0016 (8) | −0.0072 (7) | 0.0009 (8) |
C9 | 0.0453 (10) | 0.0538 (12) | 0.0279 (9) | −0.0024 (9) | −0.0022 (7) | −0.0002 (8) |
C10 | 0.0359 (9) | 0.0453 (10) | 0.0301 (9) | 0.0003 (8) | −0.0014 (7) | 0.0010 (8) |
C11 | 0.0349 (9) | 0.0287 (8) | 0.0344 (9) | 0.0014 (7) | −0.0043 (7) | 0.0036 (7) |
C12 | 0.0341 (8) | 0.0309 (9) | 0.0317 (8) | −0.0008 (7) | −0.0033 (7) | 0.0027 (7) |
C13 | 0.0348 (9) | 0.0412 (10) | 0.0462 (10) | 0.0003 (8) | −0.0078 (8) | 0.0045 (8) |
C14 | 0.0573 (12) | 0.0411 (11) | 0.0400 (10) | −0.0038 (9) | −0.0191 (9) | 0.0009 (8) |
C15 | 0.0727 (14) | 0.0436 (11) | 0.0337 (10) | 0.0077 (10) | −0.0050 (9) | −0.0050 (8) |
C16 | 0.0475 (11) | 0.0419 (10) | 0.0409 (10) | 0.0124 (9) | 0.0005 (8) | 0.0005 (8) |
C17 | 0.0369 (9) | 0.0351 (9) | 0.0429 (10) | −0.0007 (8) | −0.0076 (8) | 0.0074 (8) |
N1 | 0.0338 (7) | 0.0434 (8) | 0.0267 (7) | 0.0016 (6) | −0.0025 (6) | 0.0036 (6) |
N2 | 0.0442 (9) | 0.0431 (9) | 0.0333 (8) | −0.0078 (7) | −0.0150 (6) | 0.0049 (7) |
N3 | 0.0719 (13) | 0.0590 (11) | 0.0423 (10) | 0.0081 (10) | −0.0188 (9) | 0.0060 (9) |
O1 | 0.0997 (13) | 0.0862 (13) | 0.0481 (9) | −0.0073 (11) | −0.0204 (9) | 0.0270 (9) |
O2 | 0.0658 (11) | 0.1458 (19) | 0.0794 (13) | 0.0075 (12) | −0.0338 (9) | 0.0346 (12) |
O3 | 0.0401 (8) | 0.0599 (9) | 0.0710 (10) | 0.0141 (7) | −0.0141 (7) | 0.0035 (8) |
O4 | 0.0517 (8) | 0.0608 (9) | 0.0375 (7) | 0.0066 (7) | −0.0175 (6) | −0.0052 (7) |
O5 | 0.0427 (7) | 0.0608 (9) | 0.0368 (7) | 0.0106 (7) | −0.0033 (5) | −0.0085 (6) |
C1—C2 | 1.394 (2) | C10—N1 | 1.462 (2) |
C1—C6 | 1.398 (2) | C10—H10A | 0.9700 |
C1—N1 | 1.401 (2) | C10—H10B | 0.9700 |
C2—C3 | 1.378 (2) | C11—C16 | 1.391 (2) |
C2—H2 | 0.9300 | C11—C12 | 1.399 (2) |
C3—C4 | 1.375 (3) | C11—C17 | 1.504 (2) |
C3—H3 | 0.9300 | C12—O5 | 1.359 (2) |
C4—C5 | 1.373 (3) | C12—C13 | 1.393 (2) |
C4—N3 | 1.458 (2) | C13—C14 | 1.375 (3) |
C5—C6 | 1.378 (2) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—C15 | 1.381 (3) |
C6—H6 | 0.9300 | C14—H14 | 0.9300 |
C7—N1 | 1.470 (2) | C15—C16 | 1.376 (3) |
C7—C8 | 1.510 (2) | C15—H15 | 0.9300 |
C7—H7A | 0.9700 | C16—H16 | 0.9300 |
C7—H7B | 0.9700 | C17—O3 | 1.237 (2) |
C8—N2 | 1.483 (2) | C17—O4 | 1.277 (2) |
C8—H8A | 0.9700 | N2—H21 | 0.918 (15) |
C8—H8B | 0.9700 | N2—H22 | 0.907 (15) |
C9—N2 | 1.489 (2) | N3—O1 | 1.221 (2) |
C9—C10 | 1.514 (2) | N3—O2 | 1.227 (3) |
C9—H9A | 0.9700 | O5—H5O | 0.855 (15) |
C9—H9B | 0.9700 | ||
C2—C1—C6 | 118.13 (15) | C9—C10—H10A | 109.8 |
C2—C1—N1 | 122.42 (15) | N1—C10—H10B | 109.8 |
C6—C1—N1 | 119.41 (15) | C9—C10—H10B | 109.8 |
C3—C2—C1 | 120.64 (17) | H10A—C10—H10B | 108.2 |
C3—C2—H2 | 119.7 | C16—C11—C12 | 118.20 (15) |
C1—C2—H2 | 119.7 | C16—C11—C17 | 120.64 (16) |
C4—C3—C2 | 119.66 (17) | C12—C11—C17 | 121.15 (15) |
C4—C3—H3 | 120.2 | O5—C12—C13 | 117.97 (15) |
C2—C3—H3 | 120.2 | O5—C12—C11 | 121.87 (14) |
C5—C4—C3 | 121.31 (16) | C13—C12—C11 | 120.15 (16) |
C5—C4—N3 | 119.60 (18) | C14—C13—C12 | 120.03 (17) |
C3—C4—N3 | 119.09 (18) | C14—C13—H13 | 120.0 |
C4—C5—C6 | 118.97 (18) | C12—C13—H13 | 120.0 |
C4—C5—H5 | 120.5 | C13—C14—C15 | 120.56 (17) |
C6—C5—H5 | 120.5 | C13—C14—H14 | 119.7 |
C5—C6—C1 | 121.28 (17) | C15—C14—H14 | 119.7 |
C5—C6—H6 | 119.4 | C16—C15—C14 | 119.40 (18) |
C1—C6—H6 | 119.4 | C16—C15—H15 | 120.3 |
N1—C7—C8 | 111.35 (14) | C14—C15—H15 | 120.3 |
N1—C7—H7A | 109.4 | C15—C16—C11 | 121.61 (17) |
C8—C7—H7A | 109.4 | C15—C16—H16 | 119.2 |
N1—C7—H7B | 109.4 | C11—C16—H16 | 119.2 |
C8—C7—H7B | 109.4 | O3—C17—O4 | 123.89 (16) |
H7A—C7—H7B | 108.0 | O3—C17—C11 | 119.89 (17) |
N2—C8—C7 | 110.44 (14) | O4—C17—C11 | 116.22 (15) |
N2—C8—H8A | 109.6 | C1—N1—C10 | 117.67 (13) |
C7—C8—H8A | 109.6 | C1—N1—C7 | 116.15 (13) |
N2—C8—H8B | 109.6 | C10—N1—C7 | 112.18 (13) |
C7—C8—H8B | 109.6 | C8—N2—C9 | 110.67 (14) |
H8A—C8—H8B | 108.1 | C8—N2—H21 | 109.9 (13) |
N2—C9—C10 | 109.57 (14) | C9—N2—H21 | 108.5 (12) |
N2—C9—H9A | 109.8 | C8—N2—H22 | 105.9 (12) |
C10—C9—H9A | 109.8 | C9—N2—H22 | 112.8 (13) |
N2—C9—H9B | 109.8 | H21—N2—H22 | 109.1 (18) |
C10—C9—H9B | 109.8 | O1—N3—O2 | 123.11 (18) |
H9A—C9—H9B | 108.2 | O1—N3—C4 | 118.53 (19) |
N1—C10—C9 | 109.44 (14) | O2—N3—C4 | 118.3 (2) |
N1—C10—H10A | 109.8 | C12—O5—H5O | 105.3 (15) |
C6—C1—C2—C3 | 0.7 (3) | C12—C11—C16—C15 | −2.0 (3) |
N1—C1—C2—C3 | −177.07 (17) | C17—C11—C16—C15 | 177.55 (18) |
C1—C2—C3—C4 | 0.5 (3) | C16—C11—C17—O3 | −6.2 (3) |
C2—C3—C4—C5 | −1.1 (3) | C12—C11—C17—O3 | 173.34 (17) |
C2—C3—C4—N3 | 178.25 (18) | C16—C11—C17—O4 | 173.08 (17) |
C3—C4—C5—C6 | 0.5 (3) | C12—C11—C17—O4 | −7.4 (2) |
N3—C4—C5—C6 | −178.85 (17) | C2—C1—N1—C10 | 12.9 (2) |
C4—C5—C6—C1 | 0.7 (3) | C6—C1—N1—C10 | −164.78 (16) |
C2—C1—C6—C5 | −1.3 (3) | C2—C1—N1—C7 | −124.13 (18) |
N1—C1—C6—C5 | 176.53 (17) | C6—C1—N1—C7 | 58.1 (2) |
N1—C7—C8—N2 | −54.0 (2) | C9—C10—N1—C1 | 163.32 (15) |
N2—C9—C10—N1 | 59.2 (2) | C9—C10—N1—C7 | −58.00 (19) |
C16—C11—C12—O5 | −177.19 (16) | C8—C7—N1—C1 | −164.92 (15) |
C17—C11—C12—O5 | 3.3 (3) | C8—C7—N1—C10 | 55.73 (19) |
C16—C11—C12—C13 | 2.3 (3) | C7—C8—N2—C9 | 56.27 (19) |
C17—C11—C12—C13 | −177.21 (16) | C10—C9—N2—C8 | −59.12 (19) |
O5—C12—C13—C14 | 178.56 (17) | C5—C4—N3—O1 | 0.6 (3) |
C11—C12—C13—C14 | −1.0 (3) | C3—C4—N3—O1 | −178.8 (2) |
C12—C13—C14—C15 | −0.8 (3) | C5—C4—N3—O2 | −177.9 (2) |
C13—C14—C15—C16 | 1.2 (3) | C3—C4—N3—O2 | 2.7 (3) |
C14—C15—C16—C11 | 0.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O5i | 0.97 | 2.53 | 3.430 (2) | 155 |
C9—H9A···O5ii | 0.97 | 2.47 | 3.407 (2) | 164 |
N2—H21···O3iii | 0.92 (2) | 1.88 (2) | 2.784 (2) | 170 (2) |
N2—H22···O4 | 0.91 (2) | 1.79 (2) | 2.6957 (18) | 174 (2) |
O5—H5O···O4 | 0.86 (2) | 1.73 (2) | 2.5221 (17) | 152 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+3/2, y+1/2, −z+1/2. |
2C10H14N3O2+·2C7H4FO2−·3H2O | F(000) = 1576 |
Mr = 748.73 | Dx = 1.333 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 16.882 (2) Å | Cell parameters from 3000 reflections |
b = 9.719 (1) Å | θ = 2.7–27.9° |
c = 23.445 (4) Å | µ = 0.11 mm−1 |
β = 104.17 (1)° | T = 293 K |
V = 3729.7 (9) Å3 | Prism, yellow |
Z = 4 | 0.32 × 0.16 × 0.14 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 2429 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.063 |
Rotation method data acquisition using ω scans. | θmax = 25.4°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −18→20 |
Tmin = 0.887, Tmax = 1.000 | k = −10→11 |
14552 measured reflections | l = −27→28 |
6755 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.089 | Hydrogen site location: mixed |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0366P)2 + 1.3296P] where P = (Fo2 + 2Fc2)/3 |
6755 reflections | (Δ/σ)max < 0.001 |
508 parameters | Δρmax = 0.19 e Å−3 |
10 restraints | Δρmin = −0.18 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 | ||
O1C | −0.0312 (2) | 0.0993 (6) | 0.05767 (19) | 0.1313 (19) | |
O2C | −0.0276 (2) | 0.3166 (5) | 0.07469 (19) | 0.1200 (17) | |
N1C | 0.3330 (2) | 0.2257 (4) | 0.05682 (18) | 0.0771 (13) | |
N2C | 0.5029 (2) | 0.2032 (6) | 0.10503 (19) | 0.0755 (13) | |
H2CA | 0.525 (3) | 0.228 (5) | 0.0755 (15) | 0.091* | |
H2CB | 0.5443 (19) | 0.181 (4) | 0.1336 (15) | 0.091* | |
N3C | 0.0042 (3) | 0.2079 (7) | 0.0642 (2) | 0.0969 (18) | |
C1C | 0.2521 (3) | 0.2222 (5) | 0.05718 (18) | 0.0548 (12) | |
C2C | 0.2079 (3) | 0.1001 (5) | 0.0481 (2) | 0.0711 (15) | |
H2C | 0.233224 | 0.019457 | 0.040707 | 0.085* | |
C3C | 0.1267 (3) | 0.0971 (6) | 0.0501 (2) | 0.0772 (16) | |
H3C | 0.097724 | 0.014854 | 0.044109 | 0.093* | |
C4C | 0.0892 (3) | 0.2159 (7) | 0.0607 (2) | 0.0682 (15) | |
C5C | 0.1305 (3) | 0.3366 (6) | 0.0683 (2) | 0.0733 (15) | |
H5C | 0.104210 | 0.417170 | 0.074714 | 0.088* | |
C6C | 0.2101 (3) | 0.3398 (5) | 0.0666 (2) | 0.0683 (14) | |
H6C | 0.237594 | 0.423523 | 0.071920 | 0.082* | |
C7C | 0.3781 (3) | 0.1119 (5) | 0.0402 (2) | 0.0780 (16) | |
H7CA | 0.395409 | 0.135654 | 0.004936 | 0.094* | |
H7CB | 0.343097 | 0.031626 | 0.031706 | 0.094* | |
C8C | 0.4513 (3) | 0.0795 (5) | 0.0889 (2) | 0.0778 (15) | |
H8CA | 0.433740 | 0.046830 | 0.122885 | 0.093* | |
H8CB | 0.482818 | 0.007113 | 0.076378 | 0.093* | |
C9C | 0.4560 (3) | 0.3197 (6) | 0.1201 (2) | 0.0896 (18) | |
H9CA | 0.490449 | 0.400734 | 0.127955 | 0.107* | |
H9CB | 0.438091 | 0.298123 | 0.155397 | 0.107* | |
C10C | 0.3834 (3) | 0.3483 (5) | 0.0706 (3) | 0.0967 (19) | |
H10A | 0.351600 | 0.422484 | 0.081479 | 0.116* | |
H10B | 0.401437 | 0.376935 | 0.036203 | 0.116* | |
F1D | 0.80958 (18) | 0.2961 (4) | −0.15139 (13) | 0.1174 (11) | |
O3D | 0.56389 (18) | 0.2765 (4) | 0.01163 (13) | 0.0890 (12) | |
O4D | 0.68138 (17) | 0.2812 (3) | 0.07894 (14) | 0.0732 (9) | |
C11D | 0.6858 (2) | 0.2799 (4) | −0.02171 (19) | 0.0491 (11) | |
C12D | 0.6447 (3) | 0.2743 (5) | −0.0801 (2) | 0.0695 (14) | |
H12D | 0.588034 | 0.266742 | −0.090222 | 0.083* | |
C13D | 0.6866 (3) | 0.2796 (5) | −0.1238 (2) | 0.0842 (17) | |
H13D | 0.658864 | 0.276926 | −0.163259 | 0.101* | |
C14D | 0.7692 (3) | 0.2888 (5) | −0.1075 (2) | 0.0737 (15) | |
C15D | 0.8119 (3) | 0.2932 (5) | −0.0508 (2) | 0.0707 (14) | |
H15D | 0.868565 | 0.299146 | −0.041181 | 0.085* | |
C16D | 0.7698 (3) | 0.2886 (5) | −0.0074 (2) | 0.0629 (13) | |
H16D | 0.798341 | 0.291399 | 0.031866 | 0.075* | |
C17D | 0.6400 (3) | 0.2786 (5) | 0.0263 (2) | 0.0595 (13) | |
O2B | 0.3231 (2) | 0.2769 (5) | 0.20682 (17) | 0.1045 (14) | |
O1B | 0.3290 (2) | 0.0563 (5) | 0.20074 (18) | 0.1105 (15) | |
N1B | −0.0349 (2) | 0.1235 (4) | 0.21687 (19) | 0.0790 (13) | |
N2B | −0.2044 (2) | 0.1456 (5) | 0.16528 (17) | 0.0588 (11) | |
H2BA | −0.2443 (18) | 0.172 (4) | 0.1358 (13) | 0.071* | |
H2BB | −0.227 (2) | 0.120 (4) | 0.1942 (13) | 0.071* | |
N3B | 0.2917 (3) | 0.1638 (6) | 0.20481 (18) | 0.0761 (14) | |
C1B | 0.0441 (3) | 0.1348 (5) | 0.21270 (19) | 0.0566 (13) | |
C2B | 0.0898 (3) | 0.0181 (5) | 0.2067 (2) | 0.0733 (15) | |
H2B | 0.065666 | −0.068307 | 0.204790 | 0.088* | |
C3B | 0.1698 (3) | 0.0287 (6) | 0.2037 (2) | 0.0735 (15) | |
H3B | 0.199054 | −0.050062 | 0.199530 | 0.088* | |
C4B | 0.2063 (3) | 0.1544 (7) | 0.20692 (19) | 0.0605 (14) | |
C5B | 0.1634 (3) | 0.2711 (5) | 0.21249 (18) | 0.0651 (14) | |
H5B | 0.188542 | 0.356672 | 0.214251 | 0.078* | |
C6B | 0.0836 (3) | 0.2623 (5) | 0.21548 (18) | 0.0640 (14) | |
H6B | 0.055117 | 0.342280 | 0.219424 | 0.077* | |
C7B | −0.0848 (3) | −0.0001 (5) | 0.2001 (2) | 0.0835 (16) | |
H7BA | −0.104035 | −0.032659 | 0.233468 | 0.100* | |
H7BB | −0.051975 | −0.072114 | 0.188784 | 0.100* | |
C8B | −0.1567 (3) | 0.0313 (5) | 0.1496 (2) | 0.0746 (15) | |
H8BA | −0.137606 | 0.055819 | 0.115176 | 0.090* | |
H8BB | −0.191039 | −0.049624 | 0.140231 | 0.090* | |
C9B | −0.1539 (3) | 0.2701 (5) | 0.1840 (2) | 0.0664 (14) | |
H9BA | −0.186574 | 0.340691 | 0.196546 | 0.080* | |
H9BB | −0.134516 | 0.305835 | 0.151264 | 0.080* | |
C10B | −0.0822 (3) | 0.2335 (5) | 0.2341 (2) | 0.0730 (15) | |
H10C | −0.047802 | 0.313746 | 0.245332 | 0.088* | |
H10D | −0.101734 | 0.204666 | 0.267845 | 0.088* | |
F1A | −0.49683 (18) | 0.1699 (4) | 0.43216 (14) | 0.1397 (14) | |
O4A | −0.38370 (18) | 0.0984 (4) | 0.19821 (14) | 0.0888 (11) | |
O3A | −0.26382 (17) | 0.0937 (3) | 0.26186 (12) | 0.0729 (10) | |
C11A | −0.3810 (2) | 0.1255 (4) | 0.29882 (19) | 0.0477 (11) | |
C16A | −0.4654 (3) | 0.1210 (4) | 0.2880 (2) | 0.0600 (13) | |
H16A | −0.496139 | 0.108480 | 0.249617 | 0.072* | |
C15A | −0.5051 (3) | 0.1346 (5) | 0.3326 (2) | 0.0745 (15) | |
H15A | −0.561728 | 0.129803 | 0.325026 | 0.089* | |
C14A | −0.4589 (3) | 0.1549 (6) | 0.3875 (2) | 0.0849 (17) | |
C13A | −0.3756 (3) | 0.1629 (6) | 0.4012 (2) | 0.0885 (18) | |
H13A | −0.345964 | 0.178267 | 0.439690 | 0.106* | |
C12A | −0.3368 (3) | 0.1473 (5) | 0.3559 (2) | 0.0666 (14) | |
H12A | −0.280128 | 0.151696 | 0.364060 | 0.080* | |
C17A | −0.3395 (3) | 0.1061 (5) | 0.2497 (2) | 0.0585 (13) | |
O5 | 0.6374 (2) | 0.4752 (4) | 0.15259 (17) | 0.0930 (12) | |
H5A | 0.678 (2) | 0.513 (5) | 0.1756 (19) | 0.112* | |
H5D | 0.653 (3) | 0.419 (4) | 0.131 (2) | 0.112* | |
O6 | 0.3427 (3) | 0.0628 (6) | −0.1109 (2) | 0.1407 (17) | |
H6A | 0.349 (4) | 0.042 (7) | −0.1444 (15) | 0.169* | |
H6D | 0.371 (4) | 0.135 (4) | −0.106 (3) | 0.169* | |
O7 | 0.4318 (3) | 0.3010 (5) | −0.0864 (3) | 0.1502 (18) | |
H7A | 0.473 (3) | 0.311 (7) | −0.059 (2) | 0.180* | |
H7B | 0.414 (4) | 0.373 (4) | −0.104 (3) | 0.180* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1C | 0.077 (3) | 0.203 (5) | 0.119 (4) | −0.059 (3) | 0.032 (2) | −0.048 (4) |
O2C | 0.064 (3) | 0.187 (5) | 0.111 (4) | 0.008 (3) | 0.025 (2) | −0.019 (4) |
N1C | 0.045 (3) | 0.063 (3) | 0.120 (4) | 0.003 (2) | 0.014 (2) | −0.015 (3) |
N2C | 0.043 (3) | 0.123 (4) | 0.060 (3) | 0.001 (3) | 0.012 (2) | 0.013 (3) |
N3C | 0.062 (4) | 0.165 (6) | 0.060 (3) | −0.010 (4) | 0.010 (3) | −0.029 (4) |
C1C | 0.041 (3) | 0.065 (3) | 0.052 (3) | −0.002 (3) | 0.000 (2) | 0.002 (3) |
C2C | 0.055 (3) | 0.075 (4) | 0.080 (4) | −0.008 (3) | 0.012 (3) | −0.012 (3) |
C3C | 0.059 (4) | 0.091 (5) | 0.078 (4) | −0.026 (3) | 0.011 (3) | −0.013 (3) |
C4C | 0.040 (3) | 0.111 (5) | 0.051 (3) | −0.003 (4) | 0.007 (2) | −0.009 (4) |
C5C | 0.053 (3) | 0.091 (5) | 0.073 (4) | 0.010 (3) | 0.010 (3) | −0.003 (3) |
C6C | 0.049 (3) | 0.065 (4) | 0.088 (4) | 0.003 (3) | 0.013 (3) | 0.000 (3) |
C7C | 0.052 (3) | 0.088 (4) | 0.090 (4) | 0.003 (3) | 0.011 (3) | −0.019 (3) |
C8C | 0.058 (3) | 0.089 (4) | 0.089 (4) | 0.009 (3) | 0.022 (3) | 0.007 (3) |
C9C | 0.063 (4) | 0.103 (5) | 0.110 (5) | −0.023 (3) | 0.035 (3) | −0.025 (4) |
C10C | 0.054 (3) | 0.069 (4) | 0.162 (6) | −0.001 (3) | 0.017 (3) | 0.004 (4) |
F1D | 0.107 (2) | 0.179 (3) | 0.084 (2) | −0.010 (2) | 0.0579 (19) | −0.012 (2) |
O3D | 0.048 (2) | 0.157 (3) | 0.063 (2) | 0.004 (2) | 0.0152 (17) | 0.019 (2) |
O4D | 0.065 (2) | 0.100 (3) | 0.054 (2) | 0.0097 (18) | 0.0136 (17) | 0.009 (2) |
C11D | 0.045 (3) | 0.053 (3) | 0.050 (3) | 0.000 (2) | 0.014 (2) | 0.005 (3) |
C12D | 0.056 (3) | 0.090 (4) | 0.059 (4) | −0.005 (3) | 0.009 (3) | −0.008 (3) |
C13D | 0.084 (4) | 0.124 (5) | 0.048 (3) | −0.010 (4) | 0.024 (3) | −0.017 (3) |
C14D | 0.073 (4) | 0.090 (4) | 0.074 (4) | −0.006 (3) | 0.048 (3) | −0.008 (4) |
C15D | 0.058 (3) | 0.085 (4) | 0.069 (4) | 0.003 (3) | 0.016 (3) | 0.002 (4) |
C16D | 0.058 (3) | 0.080 (4) | 0.054 (3) | 0.004 (3) | 0.019 (3) | 0.011 (3) |
C17D | 0.056 (3) | 0.072 (4) | 0.050 (3) | 0.004 (3) | 0.012 (3) | 0.008 (3) |
O2B | 0.073 (3) | 0.147 (4) | 0.101 (3) | −0.043 (3) | 0.036 (2) | −0.035 (3) |
O1B | 0.055 (2) | 0.145 (4) | 0.134 (4) | 0.022 (2) | 0.028 (2) | 0.016 (3) |
N1B | 0.041 (2) | 0.065 (3) | 0.131 (4) | −0.004 (2) | 0.020 (2) | −0.014 (3) |
N2B | 0.047 (3) | 0.074 (3) | 0.056 (3) | 0.008 (3) | 0.0141 (19) | 0.009 (3) |
N3B | 0.051 (3) | 0.123 (5) | 0.054 (3) | −0.006 (3) | 0.012 (2) | 0.001 (3) |
C1B | 0.039 (3) | 0.065 (4) | 0.059 (3) | 0.007 (3) | −0.001 (2) | 0.002 (3) |
C2B | 0.044 (3) | 0.069 (4) | 0.103 (4) | 0.002 (3) | 0.010 (3) | 0.009 (3) |
C3B | 0.052 (3) | 0.080 (4) | 0.085 (4) | 0.011 (3) | 0.010 (3) | 0.006 (3) |
C4B | 0.038 (3) | 0.091 (4) | 0.050 (3) | −0.008 (3) | 0.005 (2) | 0.002 (3) |
C5B | 0.060 (3) | 0.078 (4) | 0.054 (3) | −0.010 (3) | 0.009 (2) | −0.005 (3) |
C6B | 0.053 (3) | 0.069 (4) | 0.068 (4) | −0.002 (3) | 0.010 (2) | −0.010 (3) |
C7B | 0.049 (3) | 0.066 (4) | 0.137 (5) | 0.002 (3) | 0.025 (3) | 0.003 (4) |
C8B | 0.057 (3) | 0.074 (4) | 0.100 (4) | −0.004 (3) | 0.033 (3) | −0.017 (3) |
C9B | 0.060 (3) | 0.060 (3) | 0.081 (4) | 0.004 (3) | 0.021 (3) | 0.001 (3) |
C10B | 0.052 (3) | 0.082 (4) | 0.086 (4) | 0.004 (3) | 0.018 (3) | −0.014 (3) |
F1A | 0.100 (2) | 0.246 (4) | 0.090 (2) | −0.018 (2) | 0.055 (2) | −0.043 (3) |
O4A | 0.067 (2) | 0.145 (3) | 0.051 (2) | 0.020 (2) | 0.0076 (18) | −0.003 (2) |
O3A | 0.0438 (19) | 0.116 (3) | 0.061 (2) | 0.0097 (18) | 0.0175 (16) | 0.012 (2) |
C11A | 0.042 (3) | 0.052 (3) | 0.048 (3) | 0.001 (2) | 0.010 (2) | 0.000 (3) |
C16A | 0.055 (3) | 0.070 (3) | 0.054 (3) | −0.001 (3) | 0.010 (2) | −0.005 (3) |
C15A | 0.055 (3) | 0.102 (4) | 0.070 (4) | −0.013 (3) | 0.021 (3) | −0.018 (4) |
C14A | 0.068 (4) | 0.131 (5) | 0.069 (4) | −0.011 (4) | 0.043 (3) | −0.023 (4) |
C13A | 0.075 (4) | 0.141 (5) | 0.050 (3) | −0.012 (4) | 0.017 (3) | −0.024 (4) |
C12A | 0.055 (3) | 0.090 (4) | 0.053 (3) | −0.005 (3) | 0.010 (3) | −0.009 (3) |
C17A | 0.055 (3) | 0.072 (4) | 0.050 (3) | 0.007 (3) | 0.016 (3) | 0.007 (3) |
O5 | 0.061 (2) | 0.112 (3) | 0.100 (3) | −0.002 (2) | 0.008 (2) | −0.036 (3) |
O6 | 0.115 (3) | 0.170 (5) | 0.149 (4) | −0.041 (3) | 0.056 (3) | −0.068 (4) |
O7 | 0.122 (4) | 0.128 (4) | 0.156 (5) | −0.024 (3) | −0.050 (3) | 0.019 (4) |
O1C—N3C | 1.203 (6) | N1B—C10B | 1.449 (5) |
O2C—N3C | 1.237 (6) | N1B—C7B | 1.464 (5) |
N1C—C1C | 1.368 (5) | N2B—C8B | 1.470 (5) |
N1C—C7C | 1.449 (5) | N2B—C9B | 1.483 (5) |
N1C—C10C | 1.454 (5) | N2B—H2BA | 0.875 (18) |
N2C—C9C | 1.474 (6) | N2B—H2BB | 0.892 (18) |
N2C—C8C | 1.478 (6) | N3B—C4B | 1.456 (6) |
N2C—H2CA | 0.897 (19) | C1B—C2B | 1.398 (6) |
N2C—H2CB | 0.869 (19) | C1B—C6B | 1.402 (5) |
N3C—C4C | 1.460 (6) | C2B—C3B | 1.372 (5) |
C1C—C2C | 1.391 (5) | C2B—H2B | 0.9300 |
C1C—C6C | 1.391 (5) | C3B—C4B | 1.363 (6) |
C2C—C3C | 1.382 (6) | C3B—H3B | 0.9300 |
C2C—H2C | 0.9300 | C4B—C5B | 1.369 (6) |
C3C—C4C | 1.368 (6) | C5B—C6B | 1.369 (5) |
C3C—H3C | 0.9300 | C5B—H5B | 0.9300 |
C4C—C5C | 1.354 (6) | C6B—H6B | 0.9300 |
C5C—C6C | 1.355 (5) | C7B—C8B | 1.505 (5) |
C5C—H5C | 0.9300 | C7B—H7BA | 0.9700 |
C6C—H6C | 0.9300 | C7B—H7BB | 0.9700 |
C7C—C8C | 1.495 (5) | C8B—H8BA | 0.9700 |
C7C—H7CA | 0.9700 | C8B—H8BB | 0.9700 |
C7C—H7CB | 0.9700 | C9B—C10B | 1.508 (5) |
C8C—H8CA | 0.9700 | C9B—H9BA | 0.9700 |
C8C—H8CB | 0.9700 | C9B—H9BB | 0.9700 |
C9C—C10C | 1.493 (6) | C10B—H10C | 0.9700 |
C9C—H9CA | 0.9700 | C10B—H10D | 0.9700 |
C9C—H9CB | 0.9700 | F1A—C14A | 1.363 (5) |
C10C—H10A | 0.9700 | O4A—C17A | 1.257 (5) |
C10C—H10B | 0.9700 | O3A—C17A | 1.245 (4) |
F1D—C14D | 1.368 (5) | C11A—C12A | 1.379 (5) |
O3D—C17D | 1.247 (4) | C11A—C16A | 1.386 (5) |
O4D—C17D | 1.260 (5) | C11A—C17A | 1.499 (6) |
C11D—C12D | 1.376 (5) | C16A—C15A | 1.380 (6) |
C11D—C16D | 1.377 (5) | C16A—H16A | 0.9300 |
C11D—C17D | 1.514 (6) | C15A—C14A | 1.346 (6) |
C12D—C13D | 1.381 (6) | C15A—H15A | 0.9300 |
C12D—H12D | 0.9300 | C14A—C13A | 1.365 (6) |
C13D—C14D | 1.356 (6) | C13A—C12A | 1.387 (6) |
C13D—H13D | 0.9300 | C13A—H13A | 0.9300 |
C14D—C15D | 1.350 (6) | C12A—H12A | 0.9300 |
C15D—C16D | 1.375 (6) | O5—H5A | 0.843 (19) |
C15D—H15D | 0.9300 | O5—H5D | 0.833 (19) |
C16D—H16D | 0.9300 | O6—H6A | 0.84 (2) |
O2B—N3B | 1.216 (5) | O6—H6D | 0.84 (2) |
O1B—N3B | 1.236 (5) | O7—H7A | 0.83 (2) |
N1B—C1B | 1.365 (5) | O7—H7B | 0.83 (2) |
C1C—N1C—C7C | 125.0 (4) | C10B—N1B—C7B | 111.1 (4) |
C1C—N1C—C10C | 123.3 (4) | C8B—N2B—C9B | 112.3 (3) |
C7C—N1C—C10C | 111.6 (4) | C8B—N2B—H2BA | 113 (3) |
C9C—N2C—C8C | 111.6 (4) | C9B—N2B—H2BA | 106 (3) |
C9C—N2C—H2CA | 109 (3) | C8B—N2B—H2BB | 110 (3) |
C8C—N2C—H2CA | 111 (3) | C9B—N2B—H2BB | 109 (3) |
C9C—N2C—H2CB | 113 (3) | H2BA—N2B—H2BB | 107 (4) |
C8C—N2C—H2CB | 108 (3) | O2B—N3B—O1B | 122.8 (5) |
H2CA—N2C—H2CB | 105 (4) | O2B—N3B—C4B | 118.7 (5) |
O1C—N3C—O2C | 123.3 (6) | O1B—N3B—C4B | 118.5 (5) |
O1C—N3C—C4C | 120.2 (6) | N1B—C1B—C2B | 121.0 (5) |
O2C—N3C—C4C | 116.5 (6) | N1B—C1B—C6B | 122.0 (5) |
N1C—C1C—C2C | 121.3 (5) | C2B—C1B—C6B | 117.0 (4) |
N1C—C1C—C6C | 122.0 (5) | C3B—C2B—C1B | 121.2 (5) |
C2C—C1C—C6C | 116.7 (4) | C3B—C2B—H2B | 119.4 |
C3C—C2C—C1C | 120.9 (5) | C1B—C2B—H2B | 119.4 |
C3C—C2C—H2C | 119.6 | C4B—C3B—C2B | 120.2 (5) |
C1C—C2C—H2C | 119.6 | C4B—C3B—H3B | 119.9 |
C4C—C3C—C2C | 119.6 (5) | C2B—C3B—H3B | 119.9 |
C4C—C3C—H3C | 120.2 | C3B—C4B—C5B | 120.3 (4) |
C2C—C3C—H3C | 120.2 | C3B—C4B—N3B | 119.5 (6) |
C5C—C4C—C3C | 120.6 (5) | C5B—C4B—N3B | 120.2 (5) |
C5C—C4C—N3C | 121.3 (6) | C6B—C5B—C4B | 120.3 (5) |
C3C—C4C—N3C | 118.1 (6) | C6B—C5B—H5B | 119.9 |
C4C—C5C—C6C | 119.9 (5) | C4B—C5B—H5B | 119.9 |
C4C—C5C—H5C | 120.1 | C5B—C6B—C1B | 121.1 (5) |
C6C—C5C—H5C | 120.1 | C5B—C6B—H6B | 119.5 |
C5C—C6C—C1C | 122.3 (5) | C1B—C6B—H6B | 119.5 |
C5C—C6C—H6C | 118.9 | N1B—C7B—C8B | 110.2 (4) |
C1C—C6C—H6C | 118.9 | N1B—C7B—H7BA | 109.6 |
N1C—C7C—C8C | 110.3 (4) | C8B—C7B—H7BA | 109.6 |
N1C—C7C—H7CA | 109.6 | N1B—C7B—H7BB | 109.6 |
C8C—C7C—H7CA | 109.6 | C8B—C7B—H7BB | 109.6 |
N1C—C7C—H7CB | 109.6 | H7BA—C7B—H7BB | 108.1 |
C8C—C7C—H7CB | 109.6 | N2B—C8B—C7B | 110.0 (4) |
H7CA—C7C—H7CB | 108.1 | N2B—C8B—H8BA | 109.7 |
N2C—C8C—C7C | 110.4 (4) | C7B—C8B—H8BA | 109.7 |
N2C—C8C—H8CA | 109.6 | N2B—C8B—H8BB | 109.7 |
C7C—C8C—H8CA | 109.6 | C7B—C8B—H8BB | 109.7 |
N2C—C8C—H8CB | 109.6 | H8BA—C8B—H8BB | 108.2 |
C7C—C8C—H8CB | 109.6 | N2B—C9B—C10B | 109.4 (4) |
H8CA—C8C—H8CB | 108.1 | N2B—C9B—H9BA | 109.8 |
N2C—C9C—C10C | 110.1 (4) | C10B—C9B—H9BA | 109.8 |
N2C—C9C—H9CA | 109.6 | N2B—C9B—H9BB | 109.8 |
C10C—C9C—H9CA | 109.6 | C10B—C9B—H9BB | 109.8 |
N2C—C9C—H9CB | 109.6 | H9BA—C9B—H9BB | 108.2 |
C10C—C9C—H9CB | 109.6 | N1B—C10B—C9B | 110.4 (4) |
H9CA—C9C—H9CB | 108.2 | N1B—C10B—H10C | 109.6 |
N1C—C10C—C9C | 110.2 (4) | C9B—C10B—H10C | 109.6 |
N1C—C10C—H10A | 109.6 | N1B—C10B—H10D | 109.6 |
C9C—C10C—H10A | 109.6 | C9B—C10B—H10D | 109.6 |
N1C—C10C—H10B | 109.6 | H10C—C10B—H10D | 108.1 |
C9C—C10C—H10B | 109.6 | C12A—C11A—C16A | 118.0 (4) |
H10A—C10C—H10B | 108.1 | C12A—C11A—C17A | 121.4 (4) |
C12D—C11D—C16D | 118.9 (4) | C16A—C11A—C17A | 120.5 (4) |
C12D—C11D—C17D | 120.9 (4) | C15A—C16A—C11A | 121.8 (4) |
C16D—C11D—C17D | 120.2 (4) | C15A—C16A—H16A | 119.1 |
C11D—C12D—C13D | 120.7 (4) | C11A—C16A—H16A | 119.1 |
C11D—C12D—H12D | 119.7 | C14A—C15A—C16A | 117.6 (5) |
C13D—C12D—H12D | 119.7 | C14A—C15A—H15A | 121.2 |
C14D—C13D—C12D | 118.2 (5) | C16A—C15A—H15A | 121.2 |
C14D—C13D—H13D | 120.9 | C15A—C14A—F1A | 118.7 (5) |
C12D—C13D—H13D | 120.9 | C15A—C14A—C13A | 123.8 (5) |
C15D—C14D—C13D | 122.9 (5) | F1A—C14A—C13A | 117.6 (5) |
C15D—C14D—F1D | 119.7 (5) | C14A—C13A—C12A | 117.7 (5) |
C13D—C14D—F1D | 117.4 (5) | C14A—C13A—H13A | 121.1 |
C14D—C15D—C16D | 118.7 (5) | C12A—C13A—H13A | 121.1 |
C14D—C15D—H15D | 120.7 | C11A—C12A—C13A | 121.1 (4) |
C16D—C15D—H15D | 120.7 | C11A—C12A—H12A | 119.5 |
C15D—C16D—C11D | 120.6 (4) | C13A—C12A—H12A | 119.5 |
C15D—C16D—H16D | 119.7 | O3A—C17A—O4A | 123.3 (4) |
C11D—C16D—H16D | 119.7 | O3A—C17A—C11A | 118.9 (4) |
O3D—C17D—O4D | 123.9 (4) | O4A—C17A—C11A | 117.8 (4) |
O3D—C17D—C11D | 118.3 (4) | H5A—O5—H5D | 110 (5) |
O4D—C17D—C11D | 117.8 (4) | H6A—O6—H6D | 98 (7) |
C1B—N1B—C10B | 125.1 (4) | H7A—O7—H7B | 115 (7) |
C1B—N1B—C7B | 123.7 (4) | ||
C7C—N1C—C1C—C2C | 8.1 (7) | C10B—N1B—C1B—C2B | 167.7 (4) |
C10C—N1C—C1C—C2C | −175.0 (5) | C7B—N1B—C1B—C2B | −17.0 (7) |
C7C—N1C—C1C—C6C | −172.0 (4) | C10B—N1B—C1B—C6B | −10.8 (7) |
C10C—N1C—C1C—C6C | 4.9 (7) | C7B—N1B—C1B—C6B | 164.5 (5) |
N1C—C1C—C2C—C3C | 178.4 (4) | N1B—C1B—C2B—C3B | −178.7 (4) |
C6C—C1C—C2C—C3C | −1.6 (7) | C6B—C1B—C2B—C3B | −0.1 (7) |
C1C—C2C—C3C—C4C | 0.3 (7) | C1B—C2B—C3B—C4B | 0.4 (7) |
C2C—C3C—C4C—C5C | 1.3 (8) | C2B—C3B—C4B—C5B | −0.7 (7) |
C2C—C3C—C4C—N3C | −178.2 (4) | C2B—C3B—C4B—N3B | 178.8 (4) |
O1C—N3C—C4C—C5C | −179.5 (5) | O2B—N3B—C4B—C3B | 178.9 (5) |
O2C—N3C—C4C—C5C | −0.4 (7) | O1B—N3B—C4B—C3B | −0.7 (7) |
O1C—N3C—C4C—C3C | −0.1 (7) | O2B—N3B—C4B—C5B | −1.6 (7) |
O2C—N3C—C4C—C3C | 179.0 (5) | O1B—N3B—C4B—C5B | 178.8 (5) |
C3C—C4C—C5C—C6C | −1.4 (7) | C3B—C4B—C5B—C6B | 0.6 (7) |
N3C—C4C—C5C—C6C | 178.0 (4) | N3B—C4B—C5B—C6B | −178.9 (4) |
C4C—C5C—C6C—C1C | 0.0 (7) | C4B—C5B—C6B—C1B | −0.3 (7) |
N1C—C1C—C6C—C5C | −178.5 (4) | N1B—C1B—C6B—C5B | 178.6 (4) |
C2C—C1C—C6C—C5C | 1.4 (7) | C2B—C1B—C6B—C5B | 0.0 (6) |
C1C—N1C—C7C—C8C | −124.1 (5) | C1B—N1B—C7B—C8B | −116.6 (5) |
C10C—N1C—C7C—C8C | 58.7 (5) | C10B—N1B—C7B—C8B | 59.3 (5) |
C9C—N2C—C8C—C7C | 55.0 (5) | C9B—N2B—C8B—C7B | 55.5 (5) |
N1C—C7C—C8C—N2C | −55.7 (5) | N1B—C7B—C8B—N2B | −56.2 (5) |
C8C—N2C—C9C—C10C | −55.5 (5) | C8B—N2B—C9B—C10B | −55.5 (5) |
C1C—N1C—C10C—C9C | 123.4 (5) | C1B—N1B—C10B—C9B | 116.0 (5) |
C7C—N1C—C10C—C9C | −59.4 (6) | C7B—N1B—C10B—C9B | −59.8 (5) |
N2C—C9C—C10C—N1C | 56.9 (6) | N2B—C9B—C10B—N1B | 56.8 (5) |
C16D—C11D—C12D—C13D | −1.1 (8) | C12A—C11A—C16A—C15A | −1.5 (7) |
C17D—C11D—C12D—C13D | 178.1 (5) | C17A—C11A—C16A—C15A | 178.1 (5) |
C11D—C12D—C13D—C14D | 0.8 (8) | C11A—C16A—C15A—C14A | 1.1 (8) |
C12D—C13D—C14D—C15D | −0.1 (9) | C16A—C15A—C14A—F1A | 179.4 (5) |
C12D—C13D—C14D—F1D | −179.0 (5) | C16A—C15A—C14A—C13A | 0.1 (9) |
C13D—C14D—C15D—C16D | −0.3 (9) | C15A—C14A—C13A—C12A | −0.8 (9) |
F1D—C14D—C15D—C16D | 178.6 (4) | F1A—C14A—C13A—C12A | 179.8 (5) |
C14D—C15D—C16D—C11D | −0.1 (8) | C16A—C11A—C12A—C13A | 0.6 (7) |
C12D—C11D—C16D—C15D | 0.8 (7) | C17A—C11A—C12A—C13A | −178.9 (5) |
C17D—C11D—C16D—C15D | −178.5 (5) | C14A—C13A—C12A—C11A | 0.4 (8) |
C12D—C11D—C17D—O3D | −2.2 (7) | C12A—C11A—C17A—O3A | 8.3 (7) |
C16D—C11D—C17D—O3D | 177.0 (4) | C16A—C11A—C17A—O3A | −171.2 (4) |
C12D—C11D—C17D—O4D | 178.6 (4) | C12A—C11A—C17A—O4A | −174.1 (4) |
C16D—C11D—C17D—O4D | −2.2 (7) | C16A—C11A—C17A—O4A | 6.4 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2C—H2CA···O3D | 0.90 (2) | 1.84 (2) | 2.733 (5) | 176 (4) |
N2C—H2CB···O4Ai | 0.87 (2) | 1.87 (2) | 2.726 (5) | 166 (4) |
C3C—H3C···O1Cii | 0.93 | 2.62 | 3.261 (7) | 126 |
C9C—H9CA···O5 | 0.97 | 2.51 | 3.332 (6) | 142 |
C9C—H9CB···O2B | 0.97 | 2.53 | 3.401 (6) | 149 |
C15D—H15D···F1Aiii | 0.93 | 2.52 | 3.369 (5) | 152 |
N2B—H2BA···O4Div | 0.88 (2) | 1.92 (2) | 2.764 (5) | 163 (4) |
N2B—H2BB···O3A | 0.89 (2) | 1.86 (2) | 2.739 (5) | 169 (4) |
C3B—H3B···F1Dv | 0.93 | 2.63 | 3.436 (6) | 145 |
C8B—H8BA···O1C | 0.97 | 2.53 | 3.437 (6) | 155 |
C8B—H8BB···O6ii | 0.97 | 2.49 | 3.182 (6) | 129 |
C15A—H15A···F1Dvi | 0.93 | 2.48 | 3.310 (5) | 149 |
O5—H5A···O3Avii | 0.84 (2) | 1.96 (2) | 2.794 (4) | 172 (5) |
O5—H5D···O4D | 0.83 (2) | 1.95 (2) | 2.778 (5) | 175 (5) |
O6—H6A···O4Aii | 0.84 (2) | 2.04 (4) | 2.795 (6) | 149 (7) |
O6—H6D···O7 | 0.84 (2) | 1.91 (2) | 2.744 (7) | 174 (8) |
O7—H7A···O3D | 0.83 (2) | 1.99 (3) | 2.794 (5) | 163 (7) |
O7—H7B···O5viii | 0.83 (2) | 1.93 (2) | 2.759 (6) | 172 (7) |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z; (iii) x+3/2, −y+1/2, z−1/2; (iv) x−1, y, z; (v) −x+1, −y, −z; (vi) x−3/2, −y+1/2, z+1/2; (vii) −x+1/2, y+1/2, −z+1/2; (viii) −x+1, −y+1, −z. |
C10H14N3O2+·C7H3N2O6− | F(000) = 1744 |
Mr = 419.35 | Dx = 1.443 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 27.953 (6) Å | Cell parameters from 4154 reflections |
b = 8.1422 (6) Å | θ = 2.6–27.7° |
c = 24.657 (5) Å | µ = 0.12 mm−1 |
β = 136.55 (4)° | T = 293 K |
V = 3859 (2) Å3 | Prism, orange |
Z = 8 | 0.48 × 0.48 × 0.40 mm |
Oxford Diffraction Xcalibur with Sapphire CCD diffractometer | 2838 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.015 |
Rotation method data acquisition using ω scans. | θmax = 27.7°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | h = −35→23 |
Tmin = 0.621, Tmax = 1.000 | k = −10→10 |
8107 measured reflections | l = −31→30 |
4119 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: mixed |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0543P)2 + 1.7099P] where P = (Fo2 + 2Fc2)/3 |
4119 reflections | (Δ/σ)max < 0.001 |
337 parameters | Δρmax = 0.24 e Å−3 |
262 restraints | Δρmin = −0.24 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 | 0.02612 (8) | 0.1284 (2) | 0.33993 (9) | 0.0580 (4) | |
N2 | 0.02315 (7) | −0.0150 (2) | 0.44281 (9) | 0.0452 (4) | |
H21 | −0.0246 (11) | −0.041 (2) | 0.4078 (11) | 0.054 (5)* | |
H22 | 0.0488 (10) | −0.044 (2) | 0.4941 (13) | 0.060 (6)* | |
O1 | 0.29131 (19) | 0.2691 (7) | 0.4152 (3) | 0.0936 (12) | 0.806 (10) |
O2 | 0.28193 (17) | 0.5004 (6) | 0.4502 (2) | 0.0809 (12) | 0.806 (10) |
N3 | 0.26170 (14) | 0.3612 (7) | 0.42375 (18) | 0.0631 (11) | 0.806 (10) |
C1 | 0.08449 (14) | 0.1834 (4) | 0.3603 (2) | 0.0484 (8) | 0.806 (10) |
C2 | 0.12478 (14) | 0.0767 (5) | 0.36260 (19) | 0.0547 (7) | 0.806 (10) |
H2A | 0.112973 | −0.033824 | 0.350722 | 0.066* | 0.806 (10) |
C3 | 0.18272 (12) | 0.1354 (5) | 0.38267 (16) | 0.0554 (8) | 0.806 (10) |
H3A | 0.209682 | 0.064018 | 0.384227 | 0.067* | 0.806 (10) |
C4 | 0.20037 (11) | 0.3006 (5) | 0.40042 (16) | 0.0508 (8) | 0.806 (10) |
C5 | 0.16008 (13) | 0.4073 (4) | 0.3981 (2) | 0.0621 (8) | 0.806 (10) |
H5A | 0.171890 | 0.517846 | 0.409976 | 0.075* | 0.806 (10) |
C6 | 0.10214 (14) | 0.3487 (4) | 0.3780 (2) | 0.0613 (8) | 0.806 (10) |
H6A | 0.075181 | 0.420007 | 0.376471 | 0.074* | 0.806 (10) |
O1A | 0.2969 (7) | 0.342 (2) | 0.4346 (10) | 0.082 (3) | 0.194 (10) |
O2A | 0.2788 (8) | 0.575 (2) | 0.4647 (10) | 0.092 (4) | 0.194 (10) |
N3A | 0.2640 (8) | 0.436 (2) | 0.4386 (12) | 0.067 (2) | 0.194 (10) |
C1A | 0.0900 (6) | 0.2138 (18) | 0.3708 (9) | 0.0517 (19) | 0.194 (10) |
C2A | 0.1283 (6) | 0.1262 (16) | 0.3643 (9) | 0.0519 (18) | 0.194 (10) |
H2AA | 0.116265 | 0.018417 | 0.346160 | 0.062* | 0.194 (10) |
C3A | 0.1845 (6) | 0.1997 (19) | 0.3848 (7) | 0.0519 (17) | 0.194 (10) |
H3AA | 0.210172 | 0.141125 | 0.380427 | 0.062* | 0.194 (10) |
C4A | 0.2025 (5) | 0.3609 (18) | 0.4119 (7) | 0.0608 (19) | 0.194 (10) |
C5A | 0.1642 (6) | 0.4485 (14) | 0.4184 (8) | 0.064 (2) | 0.194 (10) |
H5AA | 0.176195 | 0.556282 | 0.436505 | 0.077* | 0.194 (10) |
C6A | 0.1079 (6) | 0.3750 (17) | 0.3979 (9) | 0.062 (2) | 0.194 (10) |
H6AA | 0.082288 | 0.433576 | 0.402238 | 0.075* | 0.194 (10) |
C7 | 0.01491 (10) | −0.0473 (3) | 0.33759 (11) | 0.0549 (5) | |
H7A | 0.033495 | −0.105603 | 0.321795 | 0.066* | |
H7B | −0.034605 | −0.069484 | 0.298825 | 0.066* | |
C8 | 0.04986 (8) | −0.1082 (2) | 0.41735 (9) | 0.0453 (4) | |
H8A | 0.040452 | −0.224338 | 0.414378 | 0.054* | |
H8B | 0.099796 | −0.093615 | 0.455510 | 0.054* | |
C9 | 0.02899 (9) | 0.1652 (3) | 0.44076 (12) | 0.0566 (5) | |
H9A | 0.077636 | 0.196839 | 0.480671 | 0.068* | |
H9B | 0.006349 | 0.220270 | 0.452198 | 0.068* | |
C10 | −0.00458 (10) | 0.2165 (3) | 0.36060 (13) | 0.0665 (6) | |
H10A | −0.054078 | 0.193843 | 0.321442 | 0.080* | |
H10B | 0.001467 | 0.333748 | 0.360480 | 0.080* | |
O3 | −0.34048 (7) | 0.22513 (19) | 0.30638 (8) | 0.0637 (4) | |
O4 | −0.43333 (6) | 0.11002 (19) | 0.19876 (9) | 0.0728 (4) | |
O5 | −0.43221 (7) | −0.0409 (2) | 0.00913 (7) | 0.0831 (5) | |
O6 | −0.33493 (8) | −0.1049 (2) | 0.05113 (8) | 0.0724 (4) | |
O7 | −0.11517 (5) | 0.10834 (17) | 0.40386 (6) | 0.0513 (3) | |
O8 | −0.11592 (5) | −0.06375 (17) | 0.33293 (7) | 0.0543 (3) | |
N4 | −0.37128 (7) | 0.14524 (19) | 0.24700 (10) | 0.0500 (4) | |
N5 | −0.36882 (8) | −0.05526 (19) | 0.06164 (8) | 0.0563 (4) | |
C11 | −0.22389 (7) | 0.03229 (19) | 0.27718 (9) | 0.0358 (4) | |
C12 | −0.26050 (8) | 0.0878 (2) | 0.29183 (9) | 0.0379 (4) | |
H12 | −0.237068 | 0.124431 | 0.341817 | 0.046* | |
C13 | −0.33255 (8) | 0.0880 (2) | 0.23089 (10) | 0.0411 (4) | |
C14 | −0.36957 (8) | 0.0396 (2) | 0.15541 (10) | 0.0457 (4) | |
H14 | −0.417939 | 0.040358 | 0.115159 | 0.055* | |
C15 | −0.33151 (8) | −0.0098 (2) | 0.14243 (9) | 0.0432 (4) | |
C16 | −0.25940 (8) | −0.0165 (2) | 0.20176 (9) | 0.0398 (4) | |
H16 | −0.235352 | −0.053046 | 0.191140 | 0.048* | |
C17 | −0.14489 (7) | 0.0247 (2) | 0.34377 (9) | 0.0376 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0508 (8) | 0.0655 (11) | 0.0574 (9) | −0.0030 (8) | 0.0391 (8) | 0.0125 (8) |
N2 | 0.0288 (7) | 0.0606 (10) | 0.0318 (7) | −0.0051 (7) | 0.0173 (6) | 0.0001 (7) |
O1 | 0.0676 (16) | 0.116 (3) | 0.112 (2) | −0.0083 (18) | 0.0703 (18) | −0.002 (2) |
O2 | 0.0652 (15) | 0.090 (3) | 0.0628 (17) | −0.0371 (19) | 0.0384 (14) | −0.006 (2) |
N3 | 0.0402 (13) | 0.088 (3) | 0.0429 (14) | −0.0095 (16) | 0.0242 (12) | 0.0118 (16) |
C1 | 0.0460 (11) | 0.0555 (16) | 0.0392 (12) | −0.0086 (10) | 0.0294 (10) | 0.0044 (11) |
C2 | 0.0532 (11) | 0.0565 (18) | 0.0525 (11) | −0.0103 (12) | 0.0378 (10) | −0.0025 (13) |
C3 | 0.0523 (11) | 0.0624 (19) | 0.0520 (11) | −0.0039 (13) | 0.0380 (10) | 0.0016 (13) |
C4 | 0.0438 (10) | 0.061 (2) | 0.0415 (11) | −0.0109 (11) | 0.0291 (9) | 0.0037 (12) |
C5 | 0.0620 (12) | 0.0578 (17) | 0.0624 (15) | −0.0131 (12) | 0.0438 (12) | −0.0005 (13) |
C6 | 0.0606 (12) | 0.0606 (17) | 0.0696 (18) | −0.0051 (12) | 0.0495 (13) | 0.0016 (14) |
O1A | 0.045 (4) | 0.091 (8) | 0.075 (6) | −0.005 (5) | 0.032 (4) | 0.013 (6) |
O2A | 0.061 (5) | 0.068 (6) | 0.074 (7) | −0.026 (5) | 0.025 (4) | 0.004 (5) |
N3A | 0.049 (3) | 0.065 (4) | 0.053 (3) | −0.013 (3) | 0.026 (3) | 0.008 (3) |
C1A | 0.054 (2) | 0.060 (3) | 0.050 (2) | −0.007 (2) | 0.0401 (18) | 0.000 (2) |
C2A | 0.049 (2) | 0.058 (3) | 0.051 (2) | −0.013 (2) | 0.0370 (17) | 0.001 (2) |
C3A | 0.0483 (18) | 0.060 (3) | 0.053 (2) | −0.010 (2) | 0.0386 (16) | 0.006 (2) |
C4A | 0.0518 (19) | 0.060 (3) | 0.052 (2) | −0.012 (2) | 0.0315 (17) | 0.006 (2) |
C5A | 0.060 (2) | 0.062 (3) | 0.054 (2) | −0.014 (2) | 0.0357 (19) | 0.000 (2) |
C6A | 0.060 (2) | 0.058 (3) | 0.056 (3) | −0.014 (2) | 0.0379 (19) | 0.000 (2) |
C7 | 0.0513 (10) | 0.0639 (13) | 0.0459 (10) | −0.0144 (9) | 0.0341 (9) | −0.0059 (9) |
C8 | 0.0346 (8) | 0.0487 (10) | 0.0395 (9) | −0.0048 (7) | 0.0227 (7) | −0.0014 (8) |
C9 | 0.0436 (9) | 0.0572 (12) | 0.0699 (13) | −0.0088 (9) | 0.0415 (10) | −0.0121 (10) |
C10 | 0.0492 (10) | 0.0591 (13) | 0.0887 (15) | 0.0088 (10) | 0.0493 (11) | 0.0230 (11) |
O3 | 0.0575 (8) | 0.0796 (10) | 0.0590 (8) | 0.0076 (7) | 0.0439 (7) | −0.0009 (8) |
O4 | 0.0396 (7) | 0.0735 (10) | 0.0930 (11) | 0.0004 (7) | 0.0441 (8) | −0.0027 (8) |
O5 | 0.0490 (8) | 0.0826 (11) | 0.0350 (7) | 0.0164 (7) | 0.0035 (6) | −0.0085 (7) |
O6 | 0.0707 (9) | 0.0865 (11) | 0.0444 (8) | −0.0093 (8) | 0.0367 (7) | −0.0170 (7) |
O7 | 0.0331 (6) | 0.0708 (9) | 0.0299 (6) | −0.0012 (6) | 0.0163 (5) | −0.0073 (6) |
O8 | 0.0301 (6) | 0.0648 (8) | 0.0530 (7) | −0.0033 (6) | 0.0253 (6) | −0.0166 (6) |
N4 | 0.0391 (8) | 0.0462 (9) | 0.0597 (10) | 0.0086 (7) | 0.0341 (8) | 0.0102 (8) |
N5 | 0.0507 (9) | 0.0451 (9) | 0.0328 (8) | 0.0016 (7) | 0.0172 (7) | −0.0044 (7) |
C11 | 0.0291 (7) | 0.0349 (9) | 0.0316 (8) | 0.0000 (6) | 0.0182 (6) | 0.0014 (7) |
C12 | 0.0327 (7) | 0.0384 (9) | 0.0313 (8) | 0.0006 (7) | 0.0195 (7) | 0.0015 (7) |
C13 | 0.0327 (8) | 0.0366 (9) | 0.0433 (9) | 0.0042 (7) | 0.0241 (7) | 0.0044 (7) |
C14 | 0.0273 (7) | 0.0395 (9) | 0.0396 (9) | 0.0024 (7) | 0.0143 (7) | 0.0008 (7) |
C15 | 0.0360 (8) | 0.0366 (9) | 0.0284 (8) | 0.0008 (7) | 0.0140 (7) | −0.0017 (7) |
C16 | 0.0351 (8) | 0.0393 (9) | 0.0332 (8) | 0.0012 (7) | 0.0209 (7) | −0.0004 (7) |
C17 | 0.0291 (7) | 0.0422 (9) | 0.0319 (8) | −0.0022 (7) | 0.0190 (7) | 0.0014 (7) |
N1—C1 | 1.388 (3) | C5A—C6A | 1.3900 |
N1—C7 | 1.457 (3) | C5A—H5AA | 0.9300 |
N1—C10 | 1.465 (3) | C6A—H6AA | 0.9300 |
N1—C1A | 1.508 (9) | C7—C8 | 1.509 (3) |
N2—C9 | 1.481 (3) | C7—H7A | 0.9700 |
N2—C8 | 1.486 (2) | C7—H7B | 0.9700 |
N2—H21 | 0.95 (2) | C8—H8A | 0.9700 |
N2—H22 | 0.92 (2) | C8—H8B | 0.9700 |
O1—N3 | 1.243 (4) | C9—C10 | 1.506 (3) |
O2—N3 | 1.222 (4) | C9—H9A | 0.9700 |
N3—C4 | 1.443 (3) | C9—H9B | 0.9700 |
C1—C2 | 1.3900 | C10—H10A | 0.9700 |
C1—C6 | 1.3900 | C10—H10B | 0.9700 |
C2—C3 | 1.3900 | O3—N4 | 1.216 (2) |
C2—H2A | 0.9300 | O4—N4 | 1.229 (2) |
C3—C4 | 1.3900 | O5—N5 | 1.224 (2) |
C3—H3A | 0.9300 | O6—N5 | 1.219 (2) |
C4—C5 | 1.3900 | O7—C17 | 1.250 (2) |
C5—C6 | 1.3900 | O8—C17 | 1.2491 (19) |
C5—H5A | 0.9300 | N4—C13 | 1.473 (2) |
C6—H6A | 0.9300 | N5—C15 | 1.475 (2) |
O1A—N3A | 1.251 (16) | C11—C12 | 1.385 (2) |
O2A—N3A | 1.217 (15) | C11—C16 | 1.386 (2) |
N3A—C4A | 1.455 (12) | C11—C17 | 1.520 (2) |
C1A—C2A | 1.3900 | C12—C13 | 1.386 (2) |
C1A—C6A | 1.3900 | C12—H12 | 0.9300 |
C2A—C3A | 1.3900 | C13—C14 | 1.376 (2) |
C2A—H2AA | 0.9300 | C14—C15 | 1.375 (3) |
C3A—C4A | 1.3900 | C14—H14 | 0.9300 |
C3A—H3AA | 0.9300 | C15—C16 | 1.387 (2) |
C4A—C5A | 1.3900 | C16—H16 | 0.9300 |
C1—N1—C7 | 119.6 (2) | C1A—C6A—H6AA | 120.0 |
C1—N1—C10 | 123.3 (2) | N1—C7—C8 | 110.72 (15) |
C7—N1—C10 | 109.32 (15) | N1—C7—H7A | 109.5 |
C7—N1—C1A | 127.9 (6) | C8—C7—H7A | 109.5 |
C10—N1—C1A | 112.1 (6) | N1—C7—H7B | 109.5 |
C9—N2—C8 | 112.95 (14) | C8—C7—H7B | 109.5 |
C9—N2—H21 | 108.0 (12) | H7A—C7—H7B | 108.1 |
C8—N2—H21 | 107.8 (11) | N2—C8—C7 | 109.52 (15) |
C9—N2—H22 | 108.0 (12) | N2—C8—H8A | 109.8 |
C8—N2—H22 | 108.5 (12) | C7—C8—H8A | 109.8 |
H21—N2—H22 | 111.6 (17) | N2—C8—H8B | 109.8 |
O2—N3—O1 | 122.9 (3) | C7—C8—H8B | 109.8 |
O2—N3—C4 | 119.0 (3) | H8A—C8—H8B | 108.2 |
O1—N3—C4 | 118.1 (3) | N2—C9—C10 | 109.91 (17) |
N1—C1—C2 | 121.22 (19) | N2—C9—H9A | 109.7 |
N1—C1—C6 | 118.78 (19) | C10—C9—H9A | 109.7 |
C2—C1—C6 | 120.0 | N2—C9—H9B | 109.7 |
C3—C2—C1 | 120.0 | C10—C9—H9B | 109.7 |
C3—C2—H2A | 120.0 | H9A—C9—H9B | 108.2 |
C1—C2—H2A | 120.0 | N1—C10—C9 | 110.88 (16) |
C2—C3—C4 | 120.0 | N1—C10—H10A | 109.5 |
C2—C3—H3A | 120.0 | C9—C10—H10A | 109.5 |
C4—C3—H3A | 120.0 | N1—C10—H10B | 109.5 |
C5—C4—C3 | 120.0 | C9—C10—H10B | 109.5 |
C5—C4—N3 | 119.7 (2) | H10A—C10—H10B | 108.1 |
C3—C4—N3 | 120.3 (2) | O3—N4—O4 | 123.95 (17) |
C4—C5—C6 | 120.0 | O3—N4—C13 | 118.51 (14) |
C4—C5—H5A | 120.0 | O4—N4—C13 | 117.53 (17) |
C6—C5—H5A | 120.0 | O6—N5—O5 | 123.96 (17) |
C5—C6—C1 | 120.0 | O6—N5—C15 | 118.28 (15) |
C5—C6—H6A | 120.0 | O5—N5—C15 | 117.76 (19) |
C1—C6—H6A | 120.0 | C12—C11—C16 | 119.88 (14) |
O2A—N3A—O1A | 128.2 (14) | C12—C11—C17 | 120.03 (14) |
O2A—N3A—C4A | 117.8 (13) | C16—C11—C17 | 120.08 (15) |
O1A—N3A—C4A | 114.0 (13) | C11—C12—C13 | 119.02 (15) |
C2A—C1A—C6A | 120.0 | C11—C12—H12 | 120.5 |
C2A—C1A—N1 | 115.7 (8) | C13—C12—H12 | 120.5 |
C6A—C1A—N1 | 124.0 (8) | C14—C13—C12 | 122.68 (17) |
C1A—C2A—C3A | 120.0 | C14—C13—N4 | 118.49 (15) |
C1A—C2A—H2AA | 120.0 | C12—C13—N4 | 118.82 (16) |
C3A—C2A—H2AA | 120.0 | C15—C14—C13 | 116.72 (15) |
C4A—C3A—C2A | 120.0 | C15—C14—H14 | 121.6 |
C4A—C3A—H3AA | 120.0 | C13—C14—H14 | 121.6 |
C2A—C3A—H3AA | 120.0 | C14—C15—C16 | 122.91 (16) |
C3A—C4A—C5A | 120.0 | C14—C15—N5 | 118.67 (15) |
C3A—C4A—N3A | 120.6 (8) | C16—C15—N5 | 118.41 (17) |
C5A—C4A—N3A | 119.3 (8) | C11—C16—C15 | 118.74 (16) |
C6A—C5A—C4A | 120.0 | C11—C16—H16 | 120.6 |
C6A—C5A—H5AA | 120.0 | C15—C16—H16 | 120.6 |
C4A—C5A—H5AA | 120.0 | O8—C17—O7 | 126.27 (14) |
C5A—C6A—C1A | 120.0 | O8—C17—C11 | 116.84 (14) |
C5A—C6A—H6AA | 120.0 | O7—C17—C11 | 116.90 (15) |
C7—N1—C1—C2 | 13.5 (3) | N1—C1A—C6A—C5A | −174.0 (12) |
C10—N1—C1—C2 | 159.33 (19) | C1—N1—C7—C8 | 88.7 (2) |
C7—N1—C1—C6 | −166.94 (18) | C10—N1—C7—C8 | −61.5 (2) |
C10—N1—C1—C6 | −21.1 (3) | C1A—N1—C7—C8 | 79.6 (8) |
N1—C1—C2—C3 | 179.6 (3) | C9—N2—C8—C7 | −53.44 (19) |
C6—C1—C2—C3 | 0.0 | N1—C7—C8—N2 | 57.24 (19) |
C1—C2—C3—C4 | 0.0 | C8—N2—C9—C10 | 53.10 (19) |
C2—C3—C4—C5 | 0.0 | C1—N1—C10—C9 | −87.8 (3) |
C2—C3—C4—N3 | 178.0 (2) | C7—N1—C10—C9 | 61.0 (2) |
O2—N3—C4—C5 | 8.8 (4) | C1A—N1—C10—C9 | −86.7 (7) |
O1—N3—C4—C5 | −170.6 (3) | N2—C9—C10—N1 | −56.3 (2) |
O2—N3—C4—C3 | −169.2 (3) | C16—C11—C12—C13 | 2.3 (2) |
O1—N3—C4—C3 | 11.4 (4) | C17—C11—C12—C13 | −177.66 (15) |
C3—C4—C5—C6 | 0.0 | C11—C12—C13—C14 | −2.0 (3) |
N3—C4—C5—C6 | −178.0 (2) | C11—C12—C13—N4 | 179.25 (15) |
C4—C5—C6—C1 | 0.0 | O3—N4—C13—C14 | −161.90 (16) |
N1—C1—C6—C5 | −179.6 (3) | O4—N4—C13—C14 | 17.5 (2) |
C2—C1—C6—C5 | 0.0 | O3—N4—C13—C12 | 16.9 (2) |
C7—N1—C1A—C2A | 30.4 (11) | O4—N4—C13—C12 | −163.67 (16) |
C10—N1—C1A—C2A | 170.6 (5) | C12—C13—C14—C15 | −0.1 (3) |
C7—N1—C1A—C6A | −155.4 (6) | N4—C13—C14—C15 | 178.72 (15) |
C10—N1—C1A—C6A | −15.1 (10) | C13—C14—C15—C16 | 1.9 (3) |
C6A—C1A—C2A—C3A | 0.0 | C13—C14—C15—N5 | −177.15 (15) |
N1—C1A—C2A—C3A | 174.5 (11) | O6—N5—C15—C14 | −177.23 (17) |
C1A—C2A—C3A—C4A | 0.0 | O5—N5—C15—C14 | 2.7 (3) |
C2A—C3A—C4A—C5A | 0.0 | O6—N5—C15—C16 | 3.7 (3) |
C2A—C3A—C4A—N3A | 175.8 (13) | O5—N5—C15—C16 | −176.40 (17) |
O2A—N3A—C4A—C3A | −177.1 (15) | C12—C11—C16—C15 | −0.6 (2) |
O1A—N3A—C4A—C3A | 0 (2) | C17—C11—C16—C15 | 179.33 (15) |
O2A—N3A—C4A—C5A | −1 (2) | C14—C15—C16—C11 | −1.5 (3) |
O1A—N3A—C4A—C5A | 175.8 (13) | N5—C15—C16—C11 | 177.46 (15) |
C3A—C4A—C5A—C6A | 0.0 | C12—C11—C17—O8 | 161.97 (15) |
N3A—C4A—C5A—C6A | −175.9 (13) | C16—C11—C17—O8 | −18.0 (2) |
C4A—C5A—C6A—C1A | 0.0 | C12—C11—C17—O7 | −18.5 (2) |
C2A—C1A—C6A—C5A | 0.0 | C16—C11—C17—O7 | 161.58 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21···O8 | 0.95 (2) | 1.77 (2) | 2.705 (3) | 170.7 (17) |
N2—H22···O7i | 0.92 (2) | 1.81 (2) | 2.715 (3) | 166.4 (18) |
C8—H8A···O4ii | 0.97 | 2.54 | 3.245 (3) | 130 |
C8—H8B···O2iii | 0.97 | 2.40 | 3.354 (4) | 168 |
C8—H8B···O2Aiii | 0.97 | 2.39 | 3.353 (16) | 172 |
C9—H9A···O1iii | 0.97 | 2.54 | 3.497 (5) | 171 |
C9—H9A···O1Aiii | 0.97 | 2.47 | 3.378 (14) | 155 |
C10—H10B···O4iv | 0.97 | 2.60 | 3.425 (3) | 143 |
C12—H12···O2v | 0.93 | 2.53 | 3.231 (4) | 133 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x−1/2, y−1/2, −z+1/2; (iii) −x+1/2, −y+1/2, −z+1; (iv) −x−1/2, y+1/2, −z+1/2; (v) x−1/2, y−1/2, z. |
Acknowledgements
SDA is grateful to the University of Mysore for research facilities. HSY thanks UGC for a BSR Faculty fellowship for three years.
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