The molecular and crystal structure of zwitterionic 2-{[(4-iminiumyl-3-methyl-1,4-dihydropyridin-1-yl)methyl]carbamoyl}benzoate hemihydrate is reported. The crystal structure is stabilized by a variety of hydrogen bonds and offset π–π stacking interactions.
Keywords: crystal structure, zwitterion, hydrogen bonding, π–π interactions
Abstract
The asymmetric unit of the title compound, C15H15N3O3·0.5H2O, comprises two 2-{[(4-iminiumyl-3-methyl-1,4-dihydropyridin-1-yl)methyl]carbamoyl}benzoate zwitterions (A and B) and a water molecule. The dihedral angles between the pyridine and phenyl rings in the zwitterions are 53.69 (10) and 73.56 (11)° in A and B, respectively. In the crystal, molecules are linked by N—H⋯O, O—H⋯O, C—H⋯O and C—H⋯π(ring) hydrogen bonds into a three-dimensional network. The crystal structure also features π–π interactions involving the centroids of the pyridine and phenyl rings [centroid–centroid distances = 3.5618 (12) Å in A and 3.8182 (14) Å in B].
Chemical context
Zwitterions are high-performance materials that can be used as drug protein stabilizers without affecting the activity of the drug (Keefe & Jiang, 2012 ▸). Drug protein stabilizers not only maintain the native chemical structure, but the native secondary and higher order structures necessary for biological activity and can increase the stability of the therapeutic protein and enhancs protein–substrate hydrophobic interactions without affecting the activity of the drugs. Zwitterionic polymers grafted from polysulfone (PSF) membranes show improved protein anti-fouling properties, together with good blood compatibility and cytocompatibility in comparison with the pristine PSF membrane (Yue et al., 2013 ▸). Furthermore, zwitterionic nanocarrier drugs showed excellent biocompatibility and non-fouling properties, and were found to extend blood circulation times in vivo. The study and synthesis of new zwitterions is therefore important in the search for new biomedical applications (Jin et al., 2014 ▸).
Structural commentary
The asymmetric unit of the title compound comprises two crystallographically independent 2-{[(4-iminiumyl-3-methyl-1,4-dihydropyridin-1-yl)methyl]carbamoyl}benzoate zwitterions (molecules A and B) and a cocrystallized water molecule, as shown in Fig. 1 ▸. The zwitterions are formed through protonation of the imine substituent on the pyridine ring and deprotonation of the carboxylate substituent on the benzene ring. The bond lengths and angles (Table 1 ▸) in the title compound (Fig. 1 ▸) are generally within normal ranges. However, the N3—C3 [1.335 (3) Å in both molecules] are shorter than expected for an NH2—Car single bond [1.38 (3) Å], but are similar to those found in related compounds with an N+=C double bond (Sharmila et al., 2014 ▸; Sun et al., 2015 ▸). The C—O bonds in the carboxylate units [C15A—O3A = 1.247 (3) Å and C15A—O2A = 1.257 (3) Å] in molecule A, with comparable values in molecule B, are similar to values found in other deprotonated carboxylate groups (Hemamalini & Fun, 2010 ▸).
Figure 1.
The molecular structure of the title compound, with the atom labelling and 50% probability displacement ellipsoids.
Table 1. Selected geometric parameters (Å, °).
| O1A—C8A | 1.220 (3) | O1B—C8B | 1.222 (3) |
| O2A—C15A | 1.257 (3) | O2B—C15B | 1.244 (3) |
| O3A—C15A | 1.247 (3) | O3B—C15B | 1.249 (3) |
| N1A—C1A | 1.346 (3) | N1B—C7B | 1.484 (3) |
| N1A—C7A | 1.480 (3) | N1B—C1B | 1.341 (3) |
| N1A—C5A | 1.355 (3) | N1B—C5B | 1.351 (3) |
| N2A—C8A | 1.353 (3) | N2B—C7B | 1.435 (3) |
| N2A—C7A | 1.430 (3) | N2B—C8B | 1.349 (3) |
| N3A—C3A | 1.335 (3) | N3B—C3B | 1.335 (3) |
| C1A—N1A—C5A | 119.30 (18) | C1B—N1B—C5B | 119.32 (18) |
| C5A—N1A—C7A | 119.47 (17) | C1B—N1B—C7B | 120.78 (18) |
| C1A—N1A—C7A | 121.19 (17) | C5B—N1B—C7B | 119.84 (17) |
| C7A—N2A—C8A | 119.71 (18) | C7B—N2B—C8B | 120.11 (19) |
| N1A—C1A—C2A | 121.03 (19) | N1B—C1B—C2B | 121.2 (2) |
| N3A—C3A—C2A | 121.5 (2) | N3B—C3B—C2B | 122.2 (2) |
| N3A—C3A—C4A | 121.5 (2) | N3B—C3B—C4B | 120.95 (19) |
| N1A—C5A—C4A | 123.08 (19) | N1B—C5B—C4B | 123.12 (19) |
| N1A—C7A—N2A | 113.36 (16) | N1B—C7B—N2B | 113.19 (19) |
| O1A—C8A—N2A | 121.8 (2) | O1B—C8B—C9B | 121.33 (19) |
| N2A—C8A—C9A | 116.71 (18) | N2B—C8B—C9B | 116.39 (18) |
| O1A—C8A—C9A | 121.54 (18) | O1B—C8B—N2B | 122.1 (2) |
| O3A—C15A—C14A | 117.7 (2) | O2B—C15B—C14B | 117.17 (17) |
| O2A—C15A—O3A | 126.7 (2) | O2B—C15B—O3B | 125.5 (2) |
| O2A—C15A—C14A | 115.5 (2) | O3B—C15B—C14B | 117.32 (19) |
Supramolecular features
In the crystal, molecules are linked by N—H⋯O, C—H⋯O and O—H⋯O hydrogen bonds (Table 2 ▸) into a three-dimensional network. Intermolecular N3A—H1N3⋯O3A, N3A—H2N3⋯O3B, N3B—H3N3⋯O3A and N3B—H4N3⋯O3B hydrogen bonds generate 
(8) ring motifs (Fig. 2 ▸), while N2A—H2N2⋯O2B and N2B—H1N2⋯O2A hydrogen bonds form dimers with 
(14) ring motifs (Fig. 3 ▸). Molecule A is connected to molecule B through a C2A—H2AA⋯Cg1 interaction, while molecules of B are linked by C11B—H11B⋯Cg2 interactions (Cg1 and Cg2 are the centroids of the C9B–C14B and N1B/C1B–C5B rings) (Fig. 4 ▸). The crystal structure also features π–π interactions [Cg3⋯Cg3(−x, y, −z + 
) = 3.5618 (12) Å; Cg1⋯Cg4 = 3.8182 (14) Å, where Cg3 and Cg4 are the centroids of the N1A/C1A–C5A and C9A–C14A rings] (Fig. 5 ▸). An overall packing diagram, showing the three-dimensional array of parallel sheet of molecules in the ac plane is shown in Fig. 6 ▸.
Table 2. Hydrogen-bond geometry (Å, °).
Cg1 and Cg2 are the centroids of the C9B–C14B and N1B/C1B–C5B rings, respectively.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| N2A—H2N2⋯O2B | 0.88 (2) | 2.03 (2) | 2.897 (2) | 173 (2) |
| N3A—H2N3⋯O3B i | 0.93 (3) | 1.95 (3) | 2.864 (3) | 168 (2) |
| N3A—H1N3⋯O3A ii | 0.90 (2) | 2.01 (3) | 2.864 (3) | 157 (2) |
| N2B—H1N2⋯O2A | 0.90 (3) | 2.12 (3) | 3.006 (3) | 171 (3) |
| N3B—H4N3⋯O3B iii | 0.89 (2) | 2.01 (3) | 2.887 (3) | 167 (2) |
| N3B—H3N3⋯O3A iv | 0.95 (3) | 2.03 (3) | 2.935 (3) | 161 (3) |
| O1W—H1W1⋯O2B | 0.87 | 1.87 | 2.681 (3) | 155 |
| O1W—H2W1⋯O2A v | 0.86 | 1.81 | 2.581 (3) | 147 |
| C1A—H1AA⋯O1B vi | 0.93 | 2.53 | 3.355 (3) | 147 |
| C5A—H5AA⋯O1W | 0.93 | 2.27 | 3.083 (3) | 146 |
| C7A—H7AA⋯O1W | 0.97 | 2.47 | 3.139 (3) | 126 |
| C7A—H7AB⋯O1B vi | 0.97 | 2.40 | 3.336 (3) | 162 |
| C1B—H1BA⋯O1A v | 0.93 | 2.20 | 3.053 (3) | 152 |
| C2A—H2AA⋯Cg1i | 0.93 | 2.95 | 3.831 (2) | 158 |
| C11B—H11B⋯Cg2vii | 0.93 | 2.94 | 3.721 (3) | 142 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
; (v) 
; (vi) 
; (vii) 
.
Figure 2.
A partial packing diagram, with an (8) ring motif generated by N—H⋯O hydrogen bonds (dotted lines).
Figure 3.
A dimer with an (14) ring motif generated by N—H⋯O hydrogen bonds (dotted lines).
Figure 4.
A partial packing diagram of the title compound, with C—H⋯π interactions (dotted lines).
Figure 5.
The molecular packing in the title compound with two kinds of π–π interactions (dotted lines).
Figure 6.
The overall packing of the title compound, viewed along the b-axis direction, showing parallel sheets in the ac plane linked into a three-dimensional network along b.
Database survey
Eight structures containing carbamoylbenzoates were found in a search of the Cambridge Structural Database (Version 3.57; Groom et al., 2016 ▸): N-[2-(4,5,6,7-tetrahydrobenzimidazol-2-yl)ethyl]phthalamic acid tetrahydrate (Elz et al., 1983 ▸), 2-(phenylcarbamoyl)benzoic acid (Smith et al., 1983 ▸), N-(4-chlorophenyl)phthalamic acid (Mornon, 1970 ▸), 2-(pyridin-4-ylcarbamoyl)benzoate 4-aminopyridinium monohydrate (Zhu et al., 2010 ▸), phthalimide–phthalamate monohydrate (Barrett et al., 1998 ▸), bicyclo[2.2.1]heptan-2-aminium (R)-2-[(1-phenylethyl)carbamoyl]benzoate (Caille et al., 2009 ▸), bis(trimethylammonium) 7-[2-(carboxylato)benzamidoethyl]-7,8-dicarba-nido-undecaborate(10) (Batsanov et al., 2001 ▸) and (R)-1-phenylethanaminium 2-{[(2R,3R)-2,3-dimethoxy-2,3-dimethyl-2,3-dihydro-1,4-benzodioxin-6-yl]carbamoyl}benzoate (Ramarao et al., 2012 ▸).
A search for iminopyridine derivatives using 4-(λ4-azanylidene)-4H-1λ2-pyridine as the skeleton gave 15 hits, although none of these were zwitterionic derivatives comparable to the title compound. Of these, only three had aromatic rings in the cation in addition to the iminopoyridine unit (Sharmila et al., 2014 ▸; Pei et al., 2013 ▸)
Synthesis and crystallization
The title compound was obtained unexpectedly from the reaction of 0.01 mol of N-(bromomethyl)phthalimide and 0.01 mol of 4-amino-3-methylpyridine in 10 ml of dimethylformamide with a catalytic amount of potassium carbonate. The mixture was stirred in a 50 ml round-bottomed flask at room temperature for about 3 h. The progress of the reaction was monitored by thin-layer chromatography and the mixture was poured into cold water once the reaction was complete. The resulting precipitate was filtered off, washed successively with distilled water, and recrystallized from acetone solution by slow evaporation to obtain colourless block-shaped single crystals.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. The N- and O- bound H atoms were located from difference Fourier maps and the former were refined freely [N—H = 0.88 (2)–0.95 (3) Å], whereas for the latter, the distances from atom O1W were fixed at 0.86 Å, the H⋯H distance was fixed at 1.34 Å and the H atoms were refined with a riding model [U iso(H) = 1.5U eq(O), and O—H = 0.864 and 0.865 Å]. The C-bound H atoms were positioned geometrically using a riding model, with U iso(H) = 1.2 or 1.5U eq(C) (C—H = 0.93, 0.96 and 0.97 Å). A rotating-group model was applied to the methyl groups.
Table 3. Experimental details.
| Crystal data | |
| Chemical formula | C15H15N3O3·0.5H2O |
| M r | 294.31 |
| Crystal system, space group | Monoclinic, C2/c |
| Temperature (K) | 294 |
| a, b, c (Å) | 21.3157 (18), 11.9883 (8), 22.8642 (15) |
| β (°) | 103.729 (2) |
| V (Å3) | 5675.8 (7) |
| Z | 16 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.10 |
| Crystal size (mm) | 0.28 × 0.26 × 0.13 |
| Data collection | |
| Diffractometer | Bruker APEXII DUO CCD area-detector |
| Absorption correction | Multi-scan (SADABS, 2012 ▸) |
| T min, T max | 0.962, 0.996 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 65196, 5430, 3849 |
| R int | 0.052 |
| (sin θ/λ)max (Å−1) | 0.613 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.047, 0.136, 1.04 |
| No. of reflections | 5430 |
| No. of parameters | 414 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.48, −0.29 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989017007836/sj5531sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017007836/sj5531Isup2.hkl
CCDC reference: 1552520
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
AJS and HCK thank the Malaysian Government for MyBrain15 scholarships. CSCK extends his appreciation to Vidya Vikas Research & Development Centre for facilities and encouragement.
supplementary crystallographic information
Crystal data
| C15H15N3O3·0.5H2O | F(000) = 2480 |
| Mr = 294.31 | Dx = 1.378 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 8600 reflections |
| a = 21.3157 (18) Å | θ = 2.4–21.2° |
| b = 11.9883 (8) Å | µ = 0.10 mm−1 |
| c = 22.8642 (15) Å | T = 294 K |
| β = 103.729 (2)° | Block, colourless |
| V = 5675.8 (7) Å3 | 0.28 × 0.26 × 0.13 mm |
| Z = 16 |
Data collection
| Bruker APEXII DUO CCD area-detector diffractometer | 5430 independent reflections |
| Radiation source: Rotating Anode | 3849 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.052 |
| Detector resolution: 18.4 pixels mm-1 | θmax = 25.8°, θmin = 1.8° |
| φ and ω scans | h = −25→25 |
| Absorption correction: multi-scan SADABS 2014/5 | k = −14→14 |
| Tmin = 0.962, Tmax = 0.996 | l = −27→27 |
| 65196 measured reflections |
Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.136 | W = 1/[Σ2(FO2) + (0.0647P)2 + 3.8981P] where P = (FO2 + 2FC2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 5430 reflections | Δρmax = 0.48 e Å−3 |
| 414 parameters | Δρmin = −0.29 e Å−3 |
Special details
| Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
| Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1A | 0.22583 (8) | 0.40107 (12) | 0.40032 (7) | 0.0547 (5) | |
| O2A | 0.34333 (10) | 0.40853 (15) | 0.33565 (7) | 0.0715 (7) | |
| O3A | 0.38535 (9) | 0.53318 (14) | 0.40709 (8) | 0.0686 (7) | |
| N1A | 0.11034 (8) | 0.25855 (14) | 0.31440 (7) | 0.0374 (5) | |
| N2A | 0.22652 (8) | 0.23844 (15) | 0.35155 (8) | 0.0410 (6) | |
| N3A | −0.06918 (9) | 0.2157 (2) | 0.34758 (9) | 0.0475 (7) | |
| C1A | 0.07352 (10) | 0.34764 (17) | 0.31936 (9) | 0.0411 (7) | |
| C2A | 0.01405 (10) | 0.33503 (17) | 0.32906 (9) | 0.0409 (7) | |
| C3A | −0.01122 (10) | 0.22851 (17) | 0.33576 (8) | 0.0379 (6) | |
| C4A | 0.02754 (10) | 0.13531 (17) | 0.32905 (9) | 0.0414 (7) | |
| C5A | 0.08670 (10) | 0.15470 (17) | 0.31853 (9) | 0.0422 (7) | |
| C6A | 0.00423 (13) | 0.01857 (19) | 0.33375 (14) | 0.0650 (10) | |
| C7A | 0.17511 (10) | 0.27198 (19) | 0.30229 (9) | 0.0433 (7) | |
| C8A | 0.25260 (10) | 0.31309 (17) | 0.39486 (9) | 0.0395 (7) | |
| C9A | 0.31568 (10) | 0.28213 (16) | 0.43608 (9) | 0.0384 (6) | |
| C10A | 0.32083 (12) | 0.19564 (18) | 0.47694 (10) | 0.0488 (8) | |
| C11A | 0.37896 (13) | 0.1736 (2) | 0.51714 (10) | 0.0577 (9) | |
| C12A | 0.43176 (13) | 0.2375 (2) | 0.51666 (10) | 0.0598 (9) | |
| C13A | 0.42725 (11) | 0.3252 (2) | 0.47687 (10) | 0.0521 (8) | |
| C14A | 0.36955 (10) | 0.34807 (18) | 0.43589 (9) | 0.0414 (7) | |
| C15A | 0.36504 (11) | 0.43856 (19) | 0.38932 (11) | 0.0494 (8) | |
| O1B | 0.33946 (9) | 0.04329 (13) | 0.23061 (7) | 0.0606 (6) | |
| O2B | 0.29329 (7) | 0.02903 (12) | 0.34775 (7) | 0.0534 (6) | |
| O3B | 0.35853 (8) | −0.10987 (13) | 0.38676 (8) | 0.0601 (6) | |
| N1B | 0.29345 (8) | 0.24185 (14) | 0.13343 (8) | 0.0420 (6) | |
| N2B | 0.32218 (9) | 0.22607 (16) | 0.24284 (8) | 0.0446 (6) | |
| N3B | 0.35284 (10) | 0.27772 (19) | −0.02411 (9) | 0.0498 (7) | |
| C1B | 0.29850 (10) | 0.15205 (18) | 0.09987 (10) | 0.0450 (7) | |
| C2B | 0.31782 (10) | 0.16157 (17) | 0.04763 (10) | 0.0443 (7) | |
| C3B | 0.33333 (9) | 0.26616 (17) | 0.02691 (9) | 0.0391 (6) | |
| C4B | 0.32668 (10) | 0.36049 (16) | 0.06271 (9) | 0.0401 (7) | |
| C5B | 0.30681 (10) | 0.34382 (17) | 0.11433 (9) | 0.0424 (7) | |
| C6B | 0.33867 (14) | 0.47561 (19) | 0.04276 (11) | 0.0590 (9) | |
| C7B | 0.27054 (11) | 0.2309 (2) | 0.18961 (10) | 0.0491 (8) | |
| C8B | 0.35212 (10) | 0.12839 (17) | 0.26047 (9) | 0.0410 (7) | |
| C9B | 0.40518 (10) | 0.13125 (17) | 0.31648 (9) | 0.0399 (6) | |
| C10B | 0.45840 (12) | 0.1987 (2) | 0.31831 (12) | 0.0596 (9) | |
| C11B | 0.51180 (13) | 0.1928 (3) | 0.36621 (14) | 0.0736 (11) | |
| C12B | 0.51240 (12) | 0.1204 (2) | 0.41257 (13) | 0.0659 (10) | |
| C13B | 0.45962 (11) | 0.0541 (2) | 0.41153 (10) | 0.0515 (8) | |
| C14B | 0.40539 (9) | 0.05834 (16) | 0.36407 (9) | 0.0371 (6) | |
| C15B | 0.34765 (10) | −0.01351 (16) | 0.36602 (9) | 0.0386 (7) | |
| O1W | 0.18224 (9) | 0.0223 (2) | 0.26300 (9) | 0.0921 (9) | |
| H2N2 | 0.2484 (10) | 0.1778 (19) | 0.3480 (9) | 0.036 (6)* | |
| H2N3 | −0.0890 (14) | 0.279 (2) | 0.3580 (12) | 0.074 (9)* | |
| H1N3 | −0.0822 (13) | 0.148 (2) | 0.3573 (12) | 0.071 (8)* | |
| H1AA | 0.08940 | 0.41900 | 0.31600 | 0.0490* | |
| H2AA | −0.01080 | 0.39790 | 0.33140 | 0.0490* | |
| H5AA | 0.11220 | 0.09380 | 0.31390 | 0.0510* | |
| H6AA | −0.03720 | 0.00910 | 0.30630 | 0.0980* | |
| H6AB | 0.00040 | 0.00490 | 0.37410 | 0.0980* | |
| H6AC | 0.03450 | −0.03310 | 0.32380 | 0.0980* | |
| H7AA | 0.17720 | 0.22820 | 0.26710 | 0.0520* | |
| H10A | 0.28490 | 0.15200 | 0.47740 | 0.0590* | |
| H7AB | 0.18120 | 0.34960 | 0.29310 | 0.0520* | |
| H11A | 0.38210 | 0.11520 | 0.54450 | 0.0690* | |
| H12A | 0.47100 | 0.22190 | 0.54330 | 0.0720* | |
| H13A | 0.46330 | 0.36940 | 0.47750 | 0.0630* | |
| H10B | 0.45820 | 0.24840 | 0.28700 | 0.0720* | |
| H11B | 0.54740 | 0.23820 | 0.36690 | 0.0880* | |
| H1N2 | 0.3306 (14) | 0.285 (3) | 0.2678 (14) | 0.086 (10)* | |
| H12B | 0.54850 | 0.11610 | 0.44470 | 0.0790* | |
| H4N3 | 0.3539 (12) | 0.218 (2) | −0.0473 (12) | 0.061 (7)* | |
| H13B | 0.46030 | 0.00530 | 0.44330 | 0.0620* | |
| H3N3 | 0.3629 (13) | 0.348 (3) | −0.0382 (12) | 0.077 (9)* | |
| H1BA | 0.28860 | 0.08200 | 0.11260 | 0.0540* | |
| H2BA | 0.32090 | 0.09800 | 0.02520 | 0.0530* | |
| H5BA | 0.30220 | 0.40550 | 0.13760 | 0.0510* | |
| H6BA | 0.31080 | 0.48980 | 0.00390 | 0.0890* | |
| H6BB | 0.38290 | 0.48200 | 0.04030 | 0.0890* | |
| H6BC | 0.33010 | 0.52890 | 0.07120 | 0.0890* | |
| H7BA | 0.24300 | 0.29390 | 0.19280 | 0.0590* | |
| H7BB | 0.24470 | 0.16370 | 0.18730 | 0.0590* | |
| H1W1 | 0.22220 | 0.01410 | 0.28200 | 0.1380* | |
| H2W1 | 0.17600 | −0.03640 | 0.24040 | 0.1380* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1A | 0.0601 (10) | 0.0382 (8) | 0.0649 (10) | 0.0109 (7) | 0.0128 (8) | −0.0017 (7) |
| O2A | 0.0976 (14) | 0.0641 (11) | 0.0488 (10) | −0.0138 (10) | 0.0096 (9) | 0.0080 (8) |
| O3A | 0.0942 (14) | 0.0495 (10) | 0.0758 (12) | −0.0161 (9) | 0.0477 (10) | −0.0041 (9) |
| N1A | 0.0341 (9) | 0.0401 (9) | 0.0390 (9) | −0.0023 (7) | 0.0105 (7) | 0.0026 (7) |
| N2A | 0.0343 (9) | 0.0373 (10) | 0.0516 (11) | 0.0018 (8) | 0.0104 (8) | −0.0016 (8) |
| N3A | 0.0398 (11) | 0.0490 (12) | 0.0581 (12) | 0.0002 (9) | 0.0204 (9) | 0.0038 (10) |
| C1A | 0.0438 (12) | 0.0375 (11) | 0.0418 (11) | −0.0019 (9) | 0.0099 (9) | 0.0025 (9) |
| C2A | 0.0434 (12) | 0.0381 (11) | 0.0424 (11) | 0.0060 (9) | 0.0127 (9) | 0.0021 (9) |
| C3A | 0.0367 (11) | 0.0444 (11) | 0.0323 (10) | −0.0001 (9) | 0.0074 (8) | 0.0020 (8) |
| C4A | 0.0411 (12) | 0.0400 (11) | 0.0452 (12) | −0.0026 (9) | 0.0143 (9) | −0.0010 (9) |
| C5A | 0.0411 (12) | 0.0389 (11) | 0.0480 (12) | 0.0040 (9) | 0.0133 (9) | −0.0003 (9) |
| C6A | 0.0618 (16) | 0.0428 (13) | 0.100 (2) | −0.0044 (12) | 0.0381 (15) | 0.0023 (13) |
| C7A | 0.0366 (11) | 0.0497 (12) | 0.0452 (12) | −0.0024 (9) | 0.0129 (9) | 0.0045 (9) |
| C8A | 0.0425 (12) | 0.0339 (11) | 0.0455 (11) | −0.0015 (9) | 0.0171 (9) | 0.0052 (9) |
| C9A | 0.0413 (11) | 0.0391 (11) | 0.0365 (10) | 0.0014 (9) | 0.0127 (9) | −0.0008 (8) |
| C10A | 0.0564 (14) | 0.0443 (12) | 0.0490 (13) | 0.0002 (10) | 0.0192 (11) | 0.0044 (10) |
| C11A | 0.0724 (17) | 0.0582 (15) | 0.0419 (12) | 0.0077 (13) | 0.0126 (12) | 0.0107 (11) |
| C12A | 0.0611 (16) | 0.0770 (17) | 0.0366 (12) | 0.0135 (14) | 0.0022 (11) | −0.0013 (12) |
| C13A | 0.0444 (13) | 0.0623 (15) | 0.0491 (13) | −0.0056 (11) | 0.0099 (10) | −0.0072 (11) |
| C14A | 0.0432 (12) | 0.0459 (12) | 0.0370 (11) | 0.0001 (9) | 0.0134 (9) | −0.0022 (9) |
| C15A | 0.0519 (14) | 0.0446 (13) | 0.0573 (14) | −0.0082 (10) | 0.0242 (11) | −0.0001 (11) |
| O1B | 0.0794 (12) | 0.0455 (9) | 0.0485 (9) | 0.0102 (8) | −0.0015 (8) | −0.0085 (7) |
| O2B | 0.0394 (9) | 0.0426 (9) | 0.0765 (11) | 0.0006 (7) | 0.0102 (8) | 0.0035 (8) |
| O3B | 0.0658 (11) | 0.0423 (9) | 0.0775 (11) | 0.0070 (8) | 0.0277 (9) | 0.0203 (8) |
| N1B | 0.0431 (10) | 0.0390 (10) | 0.0444 (10) | 0.0052 (8) | 0.0116 (8) | 0.0069 (8) |
| N2B | 0.0538 (11) | 0.0369 (10) | 0.0439 (10) | 0.0061 (8) | 0.0133 (9) | 0.0066 (8) |
| N3B | 0.0584 (12) | 0.0475 (12) | 0.0461 (11) | 0.0049 (10) | 0.0176 (9) | −0.0073 (10) |
| C1B | 0.0418 (12) | 0.0378 (12) | 0.0522 (13) | 0.0000 (9) | 0.0046 (10) | 0.0054 (10) |
| C2B | 0.0418 (12) | 0.0376 (11) | 0.0492 (12) | 0.0057 (9) | 0.0025 (10) | −0.0055 (9) |
| C3B | 0.0315 (10) | 0.0432 (11) | 0.0405 (11) | 0.0067 (9) | 0.0044 (9) | −0.0004 (9) |
| C4B | 0.0432 (12) | 0.0358 (11) | 0.0412 (11) | 0.0028 (9) | 0.0100 (9) | 0.0011 (9) |
| C5B | 0.0483 (12) | 0.0362 (11) | 0.0433 (11) | 0.0045 (9) | 0.0120 (9) | 0.0030 (9) |
| C6B | 0.0861 (18) | 0.0434 (13) | 0.0516 (14) | −0.0042 (12) | 0.0246 (13) | −0.0004 (10) |
| C7B | 0.0484 (13) | 0.0529 (13) | 0.0495 (13) | 0.0062 (10) | 0.0189 (11) | 0.0153 (10) |
| C8B | 0.0494 (12) | 0.0362 (11) | 0.0401 (11) | 0.0022 (9) | 0.0161 (9) | 0.0025 (9) |
| C9B | 0.0391 (11) | 0.0382 (11) | 0.0443 (11) | 0.0002 (9) | 0.0140 (9) | −0.0035 (9) |
| C10B | 0.0575 (15) | 0.0606 (15) | 0.0652 (16) | −0.0133 (12) | 0.0235 (13) | 0.0054 (12) |
| C11B | 0.0470 (15) | 0.080 (2) | 0.091 (2) | −0.0225 (14) | 0.0111 (14) | −0.0056 (16) |
| C12B | 0.0423 (14) | 0.0819 (19) | 0.0674 (17) | −0.0056 (13) | 0.0008 (12) | −0.0084 (15) |
| C13B | 0.0473 (13) | 0.0583 (14) | 0.0463 (12) | 0.0031 (11) | 0.0062 (10) | −0.0013 (11) |
| C14B | 0.0378 (11) | 0.0362 (10) | 0.0379 (11) | 0.0035 (9) | 0.0105 (9) | −0.0040 (8) |
| C15B | 0.0435 (12) | 0.0343 (11) | 0.0396 (11) | 0.0032 (9) | 0.0131 (9) | 0.0008 (9) |
| O1W | 0.0648 (12) | 0.1316 (19) | 0.0752 (13) | 0.0212 (12) | 0.0074 (10) | −0.0386 (12) |
Geometric parameters (Å, º)
| O1A—C8A | 1.220 (3) | C14A—C15A | 1.507 (3) |
| O2A—C15A | 1.257 (3) | C1A—H1AA | 0.9300 |
| O3A—C15A | 1.247 (3) | C2A—H2AA | 0.9300 |
| O1W—H1W1 | 0.8700 | C5A—H5AA | 0.9300 |
| O1W—H2W1 | 0.8600 | C6A—H6AB | 0.9600 |
| N1A—C1A | 1.346 (3) | C6A—H6AA | 0.9600 |
| N1A—C7A | 1.480 (3) | C6A—H6AC | 0.9600 |
| N1A—C5A | 1.355 (3) | C7A—H7AB | 0.9700 |
| N2A—C8A | 1.353 (3) | C7A—H7AA | 0.9700 |
| N2A—C7A | 1.430 (3) | C10A—H10A | 0.9300 |
| N3A—C3A | 1.335 (3) | C11A—H11A | 0.9300 |
| N2A—H2N2 | 0.88 (2) | C12A—H12A | 0.9300 |
| N3A—H1N3 | 0.90 (2) | C13A—H13A | 0.9300 |
| N3A—H2N3 | 0.93 (3) | C1B—C2B | 1.358 (3) |
| O1B—C8B | 1.222 (3) | C2B—C3B | 1.407 (3) |
| O2B—C15B | 1.244 (3) | C3B—C4B | 1.423 (3) |
| O3B—C15B | 1.249 (3) | C4B—C6B | 1.494 (3) |
| N1B—C7B | 1.484 (3) | C4B—C5B | 1.360 (3) |
| N1B—C1B | 1.341 (3) | C8B—C9B | 1.494 (3) |
| N1B—C5B | 1.351 (3) | C9B—C10B | 1.386 (3) |
| N2B—C7B | 1.435 (3) | C9B—C14B | 1.395 (3) |
| N2B—C8B | 1.349 (3) | C10B—C11B | 1.381 (4) |
| N3B—C3B | 1.335 (3) | C11B—C12B | 1.368 (4) |
| N2B—H1N2 | 0.90 (3) | C12B—C13B | 1.373 (4) |
| N3B—H3N3 | 0.95 (3) | C13B—C14B | 1.386 (3) |
| N3B—H4N3 | 0.89 (2) | C14B—C15B | 1.512 (3) |
| C1A—C2A | 1.346 (3) | C1B—H1BA | 0.9300 |
| C2A—C3A | 1.408 (3) | C2B—H2BA | 0.9300 |
| C3A—C4A | 1.419 (3) | C5B—H5BA | 0.9300 |
| C4A—C6A | 1.498 (3) | C6B—H6BB | 0.9600 |
| C4A—C5A | 1.359 (3) | C6B—H6BA | 0.9600 |
| C8A—C9A | 1.494 (3) | C6B—H6BC | 0.9600 |
| C9A—C10A | 1.383 (3) | C7B—H7BB | 0.9700 |
| C9A—C14A | 1.395 (3) | C7B—H7BA | 0.9700 |
| C10A—C11A | 1.382 (4) | C10B—H10B | 0.9300 |
| C11A—C12A | 1.364 (4) | C11B—H11B | 0.9300 |
| C12A—C13A | 1.379 (3) | C12B—H12B | 0.9300 |
| C13A—C14A | 1.385 (3) | C13B—H13B | 0.9300 |
| H1W1—O1W—H2W1 | 102.00 | C12A—C11A—H11A | 120.00 |
| C1A—N1A—C5A | 119.30 (18) | C13A—C12A—H12A | 120.00 |
| C5A—N1A—C7A | 119.47 (17) | C11A—C12A—H12A | 120.00 |
| C1A—N1A—C7A | 121.19 (17) | C14A—C13A—H13A | 120.00 |
| C7A—N2A—C8A | 119.71 (18) | C12A—C13A—H13A | 120.00 |
| C7A—N2A—H2N2 | 119.0 (13) | C1B—N1B—C5B | 119.32 (18) |
| C8A—N2A—H2N2 | 118.7 (14) | C1B—N1B—C7B | 120.78 (18) |
| C3A—N3A—H2N3 | 117.3 (18) | C5B—N1B—C7B | 119.84 (17) |
| H2N3—N3A—H1N3 | 119 (2) | C7B—N2B—C8B | 120.11 (19) |
| C3A—N3A—H1N3 | 120.5 (18) | N1B—C1B—C2B | 121.2 (2) |
| C8B—N2B—H1N2 | 119 (2) | C1B—C2B—C3B | 121.04 (19) |
| C7B—N2B—H1N2 | 120 (2) | N3B—C3B—C2B | 122.2 (2) |
| C3B—N3B—H3N3 | 122.2 (18) | N3B—C3B—C4B | 120.95 (19) |
| C3B—N3B—H4N3 | 119.5 (17) | C2B—C3B—C4B | 116.82 (18) |
| H4N3—N3B—H3N3 | 118 (2) | C3B—C4B—C5B | 118.46 (18) |
| N1A—C1A—C2A | 121.03 (19) | C3B—C4B—C6B | 120.72 (19) |
| C1A—C2A—C3A | 121.3 (2) | C5B—C4B—C6B | 120.77 (19) |
| C2A—C3A—C4A | 117.04 (19) | N1B—C5B—C4B | 123.12 (19) |
| N3A—C3A—C2A | 121.5 (2) | N1B—C7B—N2B | 113.19 (19) |
| N3A—C3A—C4A | 121.5 (2) | O1B—C8B—C9B | 121.33 (19) |
| C3A—C4A—C6A | 121.1 (2) | N2B—C8B—C9B | 116.39 (18) |
| C3A—C4A—C5A | 118.23 (19) | O1B—C8B—N2B | 122.1 (2) |
| C5A—C4A—C6A | 120.7 (2) | C10B—C9B—C14B | 119.4 (2) |
| N1A—C5A—C4A | 123.08 (19) | C8B—C9B—C10B | 119.14 (19) |
| N1A—C7A—N2A | 113.36 (16) | C8B—C9B—C14B | 121.05 (19) |
| O1A—C8A—N2A | 121.8 (2) | C9B—C10B—C11B | 120.6 (2) |
| N2A—C8A—C9A | 116.71 (18) | C10B—C11B—C12B | 120.1 (3) |
| O1A—C8A—C9A | 121.54 (18) | C11B—C12B—C13B | 119.8 (3) |
| C8A—C9A—C14A | 118.39 (18) | C12B—C13B—C14B | 121.3 (2) |
| C10A—C9A—C14A | 119.6 (2) | C9B—C14B—C13B | 118.78 (19) |
| C8A—C9A—C10A | 121.9 (2) | C9B—C14B—C15B | 121.88 (18) |
| C9A—C10A—C11A | 120.5 (2) | C13B—C14B—C15B | 119.32 (18) |
| C10A—C11A—C12A | 119.9 (2) | O2B—C15B—C14B | 117.17 (17) |
| C11A—C12A—C13A | 120.4 (2) | O2B—C15B—O3B | 125.5 (2) |
| C12A—C13A—C14A | 120.6 (2) | O3B—C15B—C14B | 117.32 (19) |
| C9A—C14A—C15A | 119.71 (19) | C2B—C1B—H1BA | 119.00 |
| C13A—C14A—C15A | 121.2 (2) | N1B—C1B—H1BA | 119.00 |
| C9A—C14A—C13A | 119.0 (2) | C1B—C2B—H2BA | 119.00 |
| O3A—C15A—C14A | 117.7 (2) | C3B—C2B—H2BA | 119.00 |
| O2A—C15A—O3A | 126.7 (2) | C4B—C5B—H5BA | 118.00 |
| O2A—C15A—C14A | 115.5 (2) | N1B—C5B—H5BA | 118.00 |
| C2A—C1A—H1AA | 119.00 | C4B—C6B—H6BA | 109.00 |
| N1A—C1A—H1AA | 119.00 | C4B—C6B—H6BC | 110.00 |
| C3A—C2A—H2AA | 119.00 | H6BA—C6B—H6BB | 109.00 |
| C1A—C2A—H2AA | 119.00 | C4B—C6B—H6BB | 109.00 |
| N1A—C5A—H5AA | 118.00 | H6BB—C6B—H6BC | 110.00 |
| C4A—C5A—H5AA | 119.00 | H6BA—C6B—H6BC | 110.00 |
| C4A—C6A—H6AC | 109.00 | N1B—C7B—H7BB | 109.00 |
| H6AA—C6A—H6AB | 109.00 | N2B—C7B—H7BA | 109.00 |
| C4A—C6A—H6AB | 110.00 | N1B—C7B—H7BA | 109.00 |
| C4A—C6A—H6AA | 109.00 | H7BA—C7B—H7BB | 108.00 |
| H6AA—C6A—H6AC | 110.00 | N2B—C7B—H7BB | 109.00 |
| H6AB—C6A—H6AC | 109.00 | C9B—C10B—H10B | 120.00 |
| H7AA—C7A—H7AB | 108.00 | C11B—C10B—H10B | 120.00 |
| N2A—C7A—H7AB | 109.00 | C12B—C11B—H11B | 120.00 |
| N2A—C7A—H7AA | 109.00 | C10B—C11B—H11B | 120.00 |
| N1A—C7A—H7AA | 109.00 | C11B—C12B—H12B | 120.00 |
| N1A—C7A—H7AB | 109.00 | C13B—C12B—H12B | 120.00 |
| C11A—C10A—H10A | 120.00 | C12B—C13B—H13B | 119.00 |
| C9A—C10A—H10A | 120.00 | C14B—C13B—H13B | 119.00 |
| C10A—C11A—H11A | 120.00 | ||
| C5A—N1A—C1A—C2A | 0.8 (3) | C9A—C10A—C11A—C12A | 0.0 (4) |
| C7A—N1A—C1A—C2A | 178.52 (18) | C10A—C11A—C12A—C13A | 1.0 (4) |
| C1A—N1A—C5A—C4A | −1.7 (3) | C11A—C12A—C13A—C14A | −1.6 (4) |
| C7A—N1A—C5A—C4A | −179.45 (18) | C12A—C13A—C14A—C15A | −175.7 (2) |
| C1A—N1A—C7A—N2A | 112.8 (2) | C12A—C13A—C14A—C9A | 1.0 (3) |
| C5A—N1A—C7A—N2A | −69.5 (2) | C9A—C14A—C15A—O2A | −51.8 (3) |
| C8A—N2A—C7A—N1A | −88.4 (2) | C13A—C14A—C15A—O3A | −52.1 (3) |
| C7A—N2A—C8A—O1A | 15.1 (3) | C9A—C14A—C15A—O3A | 131.2 (2) |
| C7A—N2A—C8A—C9A | −165.31 (18) | C13A—C14A—C15A—O2A | 125.0 (2) |
| C7B—N1B—C5B—C4B | −178.6 (2) | N1B—C1B—C2B—C3B | 0.1 (3) |
| C1B—N1B—C7B—N2B | 97.4 (2) | C1B—C2B—C3B—N3B | 179.6 (2) |
| C5B—N1B—C7B—N2B | −85.4 (2) | C1B—C2B—C3B—C4B | −1.0 (3) |
| C5B—N1B—C1B—C2B | 1.1 (3) | N3B—C3B—C4B—C5B | −179.8 (2) |
| C7B—N1B—C1B—C2B | 178.3 (2) | N3B—C3B—C4B—C6B | 2.6 (3) |
| C1B—N1B—C5B—C4B | −1.4 (3) | C2B—C3B—C4B—C5B | 0.8 (3) |
| C8B—N2B—C7B—N1B | −83.4 (2) | C2B—C3B—C4B—C6B | −176.8 (2) |
| C7B—N2B—C8B—O1B | 4.4 (3) | C3B—C4B—C5B—N1B | 0.4 (3) |
| C7B—N2B—C8B—C9B | −179.84 (19) | C6B—C4B—C5B—N1B | 178.0 (2) |
| N1A—C1A—C2A—C3A | 1.5 (3) | O1B—C8B—C9B—C10B | 115.5 (3) |
| C1A—C2A—C3A—N3A | 177.5 (2) | O1B—C8B—C9B—C14B | −57.2 (3) |
| C1A—C2A—C3A—C4A | −2.8 (3) | N2B—C8B—C9B—C10B | −60.3 (3) |
| N3A—C3A—C4A—C5A | −178.40 (19) | N2B—C8B—C9B—C14B | 127.0 (2) |
| C2A—C3A—C4A—C6A | −178.4 (2) | C8B—C9B—C10B—C11B | −171.8 (2) |
| C2A—C3A—C4A—C5A | 2.0 (3) | C14B—C9B—C10B—C11B | 1.1 (4) |
| N3A—C3A—C4A—C6A | 1.3 (3) | C8B—C9B—C14B—C13B | 171.6 (2) |
| C6A—C4A—C5A—N1A | −179.4 (2) | C8B—C9B—C14B—C15B | −10.1 (3) |
| C3A—C4A—C5A—N1A | 0.3 (3) | C10B—C9B—C14B—C13B | −1.2 (3) |
| O1A—C8A—C9A—C10A | 111.7 (2) | C10B—C9B—C14B—C15B | 177.2 (2) |
| N2A—C8A—C9A—C14A | 116.8 (2) | C9B—C10B—C11B—C12B | −0.4 (4) |
| O1A—C8A—C9A—C14A | −63.6 (3) | C10B—C11B—C12B—C13B | −0.4 (4) |
| N2A—C8A—C9A—C10A | −67.9 (3) | C11B—C12B—C13B—C14B | 0.4 (4) |
| C14A—C9A—C10A—C11A | −0.5 (3) | C12B—C13B—C14B—C9B | 0.4 (3) |
| C8A—C9A—C14A—C13A | 175.42 (19) | C12B—C13B—C14B—C15B | −178.0 (2) |
| C8A—C9A—C14A—C15A | −7.8 (3) | C9B—C14B—C15B—O2B | −38.6 (3) |
| C10A—C9A—C14A—C13A | 0.0 (3) | C9B—C14B—C15B—O3B | 142.6 (2) |
| C10A—C9A—C14A—C15A | 176.8 (2) | C13B—C14B—C15B—O2B | 139.7 (2) |
| C8A—C9A—C10A—C11A | −175.8 (2) | C13B—C14B—C15B—O3B | −39.1 (3) |
Hydrogen-bond geometry (Å, º)
Cg1 and Cg2 are the centroids of the C9B–C14B and N1B/C1B–C5B rings, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2A—H2N2···O2B | 0.88 (2) | 2.03 (2) | 2.897 (2) | 173 (2) |
| N3A—H2N3···O3Bi | 0.93 (3) | 1.95 (3) | 2.864 (3) | 168 (2) |
| N3A—H1N3···O3Aii | 0.90 (2) | 2.01 (3) | 2.864 (3) | 157 (2) |
| N2B—H1N2···O2A | 0.90 (3) | 2.12 (3) | 3.006 (3) | 171 (3) |
| N3B—H4N3···O3Biii | 0.89 (2) | 2.01 (3) | 2.887 (3) | 167 (2) |
| N3B—H3N3···O3Aiv | 0.95 (3) | 2.03 (3) | 2.935 (3) | 161 (3) |
| O1W—H1W1···O2B | 0.87 | 1.87 | 2.681 (3) | 155 |
| O1W—H2W1···O2Av | 0.86 | 1.81 | 2.581 (3) | 147 |
| C1A—H1AA···O1Bvi | 0.93 | 2.53 | 3.355 (3) | 147 |
| C5A—H5AA···O1W | 0.93 | 2.27 | 3.083 (3) | 146 |
| C7A—H7AA···O1W | 0.97 | 2.47 | 3.139 (3) | 126 |
| C7A—H7AB···O1Bvi | 0.97 | 2.40 | 3.336 (3) | 162 |
| C1B—H1BA···O1Av | 0.93 | 2.20 | 3.053 (3) | 152 |
| C2A—H2AA···Cg1i | 0.93 | 2.95 | 3.831 (2) | 158 |
| C11B—H11B···Cg2vii | 0.93 | 2.94 | 3.721 (3) | 142 |
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x−1/2, y−1/2, z; (iii) x, −y, z−1/2; (iv) x, −y+1, z−1/2; (v) −x+1/2, y−1/2, −z+1/2; (vi) −x+1/2, y+1/2, −z+1/2; (vii) −x+1, y, −z+1/2.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989017007836/sj5531sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017007836/sj5531Isup2.hkl
CCDC reference: 1552520
Additional supporting information: crystallographic information; 3D view; checkCIF report