Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615018094/ku3164sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615018094/ku3164Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615018094/ku3164IIsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615018094/ku3164Isup4.cml |
CCDC references: 1427880; 1427879
For the past several decades, supramolecular interactions and hydrogen-bonding patterns have received considerable attention with respect to materials science and the pharmaceutical industry (Desiraju, 1989; Perumalla & Sun, 2014; Stanley et al., 2005).These interactions, such as hydrogen-bonding, stacking, electrostatic, hydrophobic and charge-transfer interactions, play an important role in molecular recognition and drug-delivery systems (Bond, 2012; Kawakami, 2012). Nucleobases [guanine (G), adenine (A), cytosine (C) and thymine (T) or uracil (U)] occur in nature as components of nucleic acids and cofactors. Adenine and its derivatives are biologically important compounds offering a variety of hydrogen-bonding donor and acceptor sites (McHugh & Erxleben, 2011; Imaz et al., 2011). Researchers are currently focusing their studies on N6-substituted adenines because of their role as plant-growth hormones and other biological applications. The cytokinin families of N6-benzyladenine, N6-furfuryladenine, trans-zeatin and 6-histaminopurine have been studied extensively due to their potential applications, such as mutation, antioxidant, proliferation, enzyme-inhibition, neurological, antitumour and parasitic treatments (Francis & Sorrell, 2001; Bressi et al., 2000; Huang et al., 2007). The N6-substituted adenine compounds exhibit an extensive variety of hydrogen-bonding patterns and supramolecular architectures (McHugh & Erxleben, 2011). 3-Hydroxypicolinic acid is a pyridine derivative having a carboxylic acid group. It is widely used for biological applications and photo-switching materials (Schlumbohm & Keller, 1990; Rode & Sobolewski, 2014). The crystal structures of various salts and complexes of 3-hydroxypicolinic acids have also been reported (Karthikeyan et al., 2014; Nirmalram et al., 2011; Betz & Gerber, 2011; Koleša-Dobravc et al., 2014). Tartaric acid has been widely used in food additives, for souring, making wine or as a leavening agent, for making silver mirrors, and in the pharmaceutical industry and in catalysis (Luner et al., 2002; Gratzer et al., 2013). Various salts and compounds of tartaric acid have been reported to date (Farrell et al., 2002; Thanigaimani et al., 2007; Smith et al., 2007; Mohandas et al., 2013). Recently, our group reported several N6-benzyladenine and N6-furfuryladenine compounds with different halides, carboxylic acids and metal complexes, with special emphasis on their hydrogen-bonding interactions and supramolecular architectures (Jennifer et al., 2014; Nirmalram et al., 2011; Tamilselvi & Muthiah, 2011; Stanley et al., 2003; Umadevi et al., 2001, 2002). Based on these interesting studies, we decided to extend our work on N6-benzoyladenine. In the present work, the hydrogen-bonding patterns of two cocrystals of N6-benzoyladenine, namely N6-benzoyladenine–3-hydroxypyridinium-2-carboxylate (3HPA) (1/1), (I), and N6-benzoyladenine–DL-tartaric acid (TA) (1/1), (II), are reported.
Compounds (I) and (II) were prepared by mixing a hot methanolic solution of N6-benzoyladenine (60 mg) with 3-hydroxypyridine-2-carboxylic acid (37 mg) or DL-tartaric acid (38 mg) in a 1:1 molar ratio and warming in a water bath for 30 min. Colourless needle-shaped crystals of both compounds were obtained by slow evaporation at room temperature.
Crystal data, data collection and structure refinement details for (I) and (II) are summarized in Table 1. H atoms were located readily in difference Fourier maps and were subsequently treated as riding atoms in geometrically idealized positions, with Uiso(H) = kUeq(O,N,C), where k = 1.5 for hydroxyl and 1.2 for all other H atoms.
The asymmetric unit of (I) consists of one molecule of N6-benzoyladenine (BA) and the zwitterion 3-hydroxypyridinium-2-carboxylate (3HPA). In this cocrystal, the N6-benzoyladenine exists in the N(7)–H tautomeric form with nonprotonated atoms N1, N3 and N9. The internal C8—N7—C5 angle [106.80 (14)°] is larger than the C8—N9—C4 angle [104.20 (14)°] and the N7—C8 bond [1.335 (2) Å] is longer than the C8—N9 bond [1.315 (2) Å]. These values are in the agreement with neutral benzoyladenine (Raghunathan & Pattabhi, 1981). The benzoyl C═O group of adenine is oriented syn with respect to the N6—C6 bond and anti with respect to the phenyl C11—C12 bond. An intramolecular N—H···O hydrogen bond between the N7—H7 group on the Hoogsteen face of the purine ring and the C10═O1 benzoyl group forms an S(7) graph-set motif (Etter, 1990). 3-Hydroxypicolinic acid exists in the zwitterionic form, i.e. 3-hydroxypyridinium-2-carboxylate. The protonation at the N atom of the pyridine ring is evident from the internal angle at N10 [C18—N10—C22 = 123.84 (15)°].
The 3HPA zwitterion of (I) is involved in intramolecular O—H···O and N—H···O hydrogen bonds, forming S(6) and S(5) ring motifs (Betz & Gerber, 2011). The carboxylate and phenolic groups of 3HPA (O3 and O4—H4) interact with the hydrogen-bonding sites (N6—H6 and N1; Watson–Crick sites) of the BA molecule through N—H···O and O—H···N hydrogen bonds, generating a ring-motif heterosynthon [graph-set R22(6); Etter, 1990] (Fig. 1). This motif is further linked by intermolecular N—H···N and C—H···O hydrogen bonds involving imidazole atoms N9 and C8 of the BA and atoms N10 and O2 of 3HPA, forming an R22(5) motif and thus generating a supramolecular chain. This supramolecular chain is further interlinked with a neighbouring chain through N7—H7···O2 hydrogen-bonded R42(10) and R46(16) ring motifs, leading to a supramolecular chain (Fig. 2a). These supramolecular chains are further extended on both sides by C21—H21···O1 hydrogen bonds to form supramolecular sheets with graph-set notation R76(28). Inversion-related 3HPA molecules and BA molecules form a graph-set R64(16) motif (Fig. 2b).
The crystal structure of (I) is further stabilized by π–π homo- and hetero-stacking interactions involving BA–BA, 3HPA–3HPA and BA–3HPA molecules. The corresponding centroid–centroid distances are Cg1–Cg1 = 3.6077 (10) Å, Cg1–Cg2 = 3.6389 (10) Å, Cg1–Cg3 = 3.6869 (12) Å, Cg2–Cg3 = 3.6390 (11) Å, Cg3–Cg5 = 3.6558 (11) Å and Cg5–Cg5 = 3.4970 (10) Å; Cg1 is the centroid of the imidazole ring, Cg2 that of the pyrimidine ring, Cg3 that of the phenyl ring and Cg5 that of the pyridine ring. These types of stacking interaction are similar to some known examples (Raghunathan & Pattabhi, 1981; Betz & Gerber, 2011; Tamilselvi & Muthiah, 2011) (Fig. 3).
The asymmetric unit of (II) contains one molecule of N6-benzoyladenine and one molecule of tartaric acid (TA). As in (I), N6-benzoyladenine exists as the N(7)—H tautomer. The bond lengths and angles of TA are in good agreement with the values found in the literature (Nie et al., 2001). The angle between the planes of the half molecules (O2/O3/C17/C18/O4 and O6/O7/C20/C19/O5) is 66.29 (10)°, which is close to the value of 54.6° observed in the TA structure. The carbon skeleton of the TA molecule is nearly planar, as evident from the C17—C18—C19—C20 torsion angle of 171.90 (15)° (Okaya et al., 1966; Mohandas et al., 2013).
The Hoogsteen face of the N6-benzoyladenine (N7 and benzoyl atom O1) of (II) interacts with the carboxylate group (O2) and the hydroxyl group (O4) of TA through N—H···O and O—H···O hydrogen bonds [graph-set R22(4)] (Fig. 1). This motif is further connected with symmetry-related adenine and TA molecules via O6—H6···N3 and O3—H3···N9 hydrogen bonds, generating an R44(20) ring motif. Moreover, O3—H3···N9 and N7—H7···O2 hydrogen bonds form another ring R22(16) motif. These motifs are further connected on either side via N6—H6···O5 and O4—H4···O1 hydrogen bonds, generating an R22(18) motif. The typical ADADAD (A is an acceptor and D is a donor) array of six hydrogen bonds (N—H···O, C—H···O and O—H···O) generates fused ring motifs R22(6), R22(5), R22(4), R22(5) and R22(6). These motifs connect on either side to BA and TA via O—H···N and C—H···O hydrogen bonds, leading to R22(7) motifs. Typical intramolecular N—H···O and O—H···O hydrogen bonds with S(7) and two S(5) ring motifs are also observed in the BA and TA molecules of (II).
The overall supramolecular three-dimensional network of hydrogen-bonding interactions in (II) is illustrated in Fig. 4. This supramolecular architecture is further stabilized by π–π hetero-stacking interactions (head-to-tail manner) between the five-membered ring of adenine and the benzene ring, with a centroid-to-centroid distance of 3.7459 (12) Å, and between the six-membered ring of adenine and the benzene ring, with a centroid-to-centroid distance of 3.6097 (12) Å (Raghunathan & Pattabhi, 1981) (Fig. 5).
In both title cocrystals, the N6-benzoyladenine molecules have an almost similar conformation, as revealed by the various torsion/dihedral angles (see above). The N6-benzoyladenine molecule maintains a near planar structure due to intramolecular hydrogen bonds. In cocrystal (I), the Watson–Crick face of BA interacts with 3HPA via O4—H4···N1 and N6—H6···O3 hydrogen bonds, whereas in (II) the Hoogsteen face of BA interacts with TA through N7—H7···O2 and O4—H4···O1 hydrogen bonds. Furthermore, the two crystal structures are stabilized by different types of stacking interaction, such as homo- and hetero-stacking interactions. Columns are formed in (I) through various homo-stacking imidazole–imidazole and pyridine–pyridine interactions, and hetero-stacking imidazole–pyrimidine, imidazole–phenyl, primidine–phenyl and phenyl–pyrimidine interactions involving the BA and 3HPA molecules. However, in (II) only hetero-stacking imidazole–phenyl and phenyl–pyrimidine interactions involving BA molecules are present.
For both compounds, data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).
C12H9N5O·C6H5NO3 | Z = 2 |
Mr = 378.35 | F(000) = 392 |
Triclinic, P1 | Dx = 1.525 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3961 (4) Å | Cell parameters from 3143 reflections |
b = 9.8673 (5) Å | θ = 3.1–29.3° |
c = 11.0680 (7) Å | µ = 0.11 mm−1 |
α = 66.137 (5)° | T = 293 K |
β = 83.459 (4)° | Prism, colourless |
γ = 79.546 (4)° | 0.25 × 0.2 × 0.08 mm |
V = 823.81 (8) Å3 |
Agilent SuperNova Dual Source diffractometer with Atlas detector | 3753 independent reflections |
Mirror monochromator | 2756 reflections with I > 2σ(I) |
Detector resolution: 10.4933 pixels mm-1 | Rint = 0.026 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −10→10 |
Tmin = 0.822, Tmax = 1 | k = −12→12 |
7594 measured reflections | l = −14→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.1401P], where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3753 reflections | Δρmax = 0.24 e Å−3 |
253 parameters | Δρmin = −0.22 e Å−3 |
C12H9N5O·C6H5NO3 | γ = 79.546 (4)° |
Mr = 378.35 | V = 823.81 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3961 (4) Å | Mo Kα radiation |
b = 9.8673 (5) Å | µ = 0.11 mm−1 |
c = 11.0680 (7) Å | T = 293 K |
α = 66.137 (5)° | 0.25 × 0.2 × 0.08 mm |
β = 83.459 (4)° |
Agilent SuperNova Dual Source diffractometer with Atlas detector | 3753 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 2756 reflections with I > 2σ(I) |
Tmin = 0.822, Tmax = 1 | Rint = 0.026 |
7594 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.24 e Å−3 |
3753 reflections | Δρmin = −0.22 e Å−3 |
253 parameters |
Experimental. 372 frames in 4 runs of ω scans. Crystal-to-detector distance = 55.0 mm. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.20565 (17) | 0.33549 (16) | 0.31307 (14) | 0.0387 (4) | |
N3 | 0.05049 (18) | 0.58065 (16) | 0.21959 (14) | 0.0397 (4) | |
N6 | 0.13666 (17) | 0.13598 (15) | 0.49501 (13) | 0.0367 (4) | |
H6 | 0.2047 | 0.0817 | 0.4627 | 0.044* | |
N7 | −0.18146 (16) | 0.38062 (15) | 0.49745 (14) | 0.0367 (3) | |
H7 | −0.207 | 0.3056 | 0.5664 | 0.044* | |
N9 | −0.20321 (17) | 0.61016 (15) | 0.33884 (14) | 0.0380 (4) | |
O1 | −0.02249 (16) | 0.13018 (14) | 0.67529 (12) | 0.0484 (4) | |
C2 | 0.1762 (2) | 0.4766 (2) | 0.22403 (18) | 0.0411 (4) | |
H2 | 0.2548 | 0.5054 | 0.156 | 0.049* | |
C4 | −0.0571 (2) | 0.52989 (18) | 0.32051 (16) | 0.0325 (4) | |
C5 | −0.04000 (19) | 0.38494 (17) | 0.41993 (15) | 0.0307 (4) | |
C6 | 0.0981 (2) | 0.28576 (18) | 0.41276 (16) | 0.0319 (4) | |
C8 | −0.2710 (2) | 0.5154 (2) | 0.44483 (18) | 0.0397 (4) | |
H8 | −0.3726 | 0.5401 | 0.4801 | 0.048* | |
C10 | 0.0788 (2) | 0.06522 (18) | 0.62129 (16) | 0.0331 (4) | |
C11 | 0.1477 (2) | −0.09553 (18) | 0.69194 (16) | 0.0337 (4) | |
C12 | 0.2962 (2) | −0.1624 (2) | 0.65767 (18) | 0.0417 (4) | |
H12 | 0.3572 | −0.1073 | 0.5844 | 0.05* | |
C13 | 0.3534 (3) | −0.3107 (2) | 0.7323 (2) | 0.0512 (5) | |
H13 | 0.4528 | −0.355 | 0.7089 | 0.061* | |
C14 | 0.2640 (3) | −0.3931 (2) | 0.8413 (2) | 0.0548 (6) | |
H14 | 0.3032 | −0.4926 | 0.8916 | 0.066* | |
C15 | 0.1169 (3) | −0.3276 (2) | 0.87503 (19) | 0.0513 (5) | |
H15 | 0.0559 | −0.3835 | 0.9479 | 0.062* | |
C16 | 0.0589 (2) | −0.1800 (2) | 0.80184 (17) | 0.0414 (4) | |
H16 | −0.0405 | −0.1365 | 0.8261 | 0.05* | |
O2 | 0.44752 (17) | −0.21633 (15) | 0.35809 (15) | 0.0612 (4) | |
O3 | 0.33716 (16) | 0.01920 (15) | 0.32401 (14) | 0.0557 (4) | |
O4 | 0.39918 (15) | 0.22854 (13) | 0.09991 (13) | 0.0472 (3) | |
H4 | 0.3473 | 0.1895 | 0.1693 | 0.071* | |
N10 | 0.68302 (16) | −0.10964 (15) | 0.16657 (13) | 0.0327 (3) | |
H10 | 0.6998 | −0.1992 | 0.226 | 0.039* | |
C17 | 0.4369 (2) | −0.0793 (2) | 0.30058 (17) | 0.0392 (4) | |
C18 | 0.55111 (19) | −0.01742 (18) | 0.18269 (16) | 0.0310 (4) | |
C19 | 0.5247 (2) | 0.12930 (18) | 0.08782 (16) | 0.0338 (4) | |
C20 | 0.6305 (2) | 0.1706 (2) | −0.02260 (17) | 0.0401 (4) | |
H20 | 0.6117 | 0.2662 | −0.0889 | 0.048* | |
C21 | 0.7627 (2) | 0.0712 (2) | −0.03463 (18) | 0.0415 (4) | |
H21 | 0.8336 | 0.0991 | −0.1085 | 0.05* | |
C22 | 0.7889 (2) | −0.0705 (2) | 0.06418 (18) | 0.0395 (4) | |
H22 | 0.8798 | −0.1379 | 0.0591 | 0.047* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0387 (8) | 0.0330 (8) | 0.0347 (8) | −0.0029 (6) | 0.0084 (7) | −0.0071 (6) |
N3 | 0.0452 (9) | 0.0309 (8) | 0.0334 (8) | −0.0047 (7) | 0.0079 (7) | −0.0059 (6) |
N6 | 0.0408 (8) | 0.0276 (7) | 0.0320 (8) | 0.0032 (6) | 0.0078 (6) | −0.0076 (6) |
N7 | 0.0344 (8) | 0.0317 (8) | 0.0346 (8) | −0.0014 (6) | 0.0076 (6) | −0.0072 (6) |
N9 | 0.0359 (8) | 0.0319 (8) | 0.0379 (8) | −0.0002 (6) | 0.0030 (7) | −0.0084 (7) |
O1 | 0.0576 (8) | 0.0373 (7) | 0.0348 (7) | 0.0059 (6) | 0.0121 (6) | −0.0072 (6) |
C2 | 0.0433 (10) | 0.0346 (9) | 0.0356 (10) | −0.0070 (8) | 0.0123 (8) | −0.0071 (8) |
C4 | 0.0336 (9) | 0.0276 (8) | 0.0324 (9) | −0.0019 (7) | 0.0006 (7) | −0.0095 (7) |
C5 | 0.0334 (9) | 0.0290 (8) | 0.0266 (8) | −0.0050 (7) | 0.0026 (7) | −0.0085 (7) |
C6 | 0.0359 (9) | 0.0275 (8) | 0.0280 (8) | −0.0031 (7) | 0.0022 (7) | −0.0081 (7) |
C8 | 0.0324 (9) | 0.0379 (10) | 0.0431 (10) | −0.0003 (7) | 0.0041 (8) | −0.0137 (8) |
C10 | 0.0349 (9) | 0.0314 (9) | 0.0288 (8) | −0.0031 (7) | 0.0015 (7) | −0.0090 (7) |
C11 | 0.0399 (9) | 0.0299 (9) | 0.0289 (8) | −0.0029 (7) | −0.0041 (7) | −0.0093 (7) |
C12 | 0.0428 (10) | 0.0382 (10) | 0.0393 (10) | −0.0013 (8) | −0.0028 (8) | −0.0120 (8) |
C13 | 0.0531 (12) | 0.0428 (11) | 0.0537 (12) | 0.0115 (9) | −0.0140 (10) | −0.0196 (10) |
C14 | 0.0789 (15) | 0.0306 (10) | 0.0482 (12) | 0.0048 (10) | −0.0236 (11) | −0.0087 (9) |
C15 | 0.0732 (15) | 0.0376 (11) | 0.0345 (10) | −0.0147 (10) | −0.0048 (10) | −0.0020 (8) |
C16 | 0.0486 (11) | 0.0377 (10) | 0.0324 (9) | −0.0072 (8) | −0.0005 (8) | −0.0081 (8) |
O2 | 0.0586 (9) | 0.0368 (8) | 0.0591 (9) | 0.0006 (6) | 0.0254 (7) | 0.0003 (7) |
O3 | 0.0581 (9) | 0.0435 (8) | 0.0535 (9) | 0.0026 (6) | 0.0238 (7) | −0.0178 (7) |
O4 | 0.0484 (8) | 0.0324 (7) | 0.0470 (8) | 0.0070 (6) | 0.0048 (6) | −0.0086 (6) |
N10 | 0.0336 (8) | 0.0276 (7) | 0.0299 (7) | −0.0015 (6) | 0.0031 (6) | −0.0066 (6) |
C17 | 0.0387 (10) | 0.0355 (10) | 0.0361 (10) | −0.0008 (8) | 0.0054 (8) | −0.0105 (8) |
C18 | 0.0315 (9) | 0.0293 (8) | 0.0297 (8) | −0.0030 (7) | 0.0035 (7) | −0.0111 (7) |
C19 | 0.0342 (9) | 0.0303 (9) | 0.0350 (9) | −0.0035 (7) | −0.0007 (7) | −0.0115 (7) |
C20 | 0.0495 (11) | 0.0323 (9) | 0.0321 (9) | −0.0092 (8) | 0.0003 (8) | −0.0054 (8) |
C21 | 0.0403 (10) | 0.0469 (11) | 0.0338 (10) | −0.0133 (8) | 0.0102 (8) | −0.0125 (8) |
C22 | 0.0322 (9) | 0.0462 (11) | 0.0392 (10) | −0.0044 (8) | 0.0067 (8) | −0.0186 (9) |
N1—C6 | 1.330 (2) | C13—C14 | 1.379 (3) |
N1—C2 | 1.339 (2) | C13—H13 | 0.93 |
N3—C2 | 1.322 (2) | C14—C15 | 1.372 (3) |
N3—C4 | 1.340 (2) | C14—H14 | 0.93 |
N6—C10 | 1.362 (2) | C15—C16 | 1.376 (3) |
N6—C6 | 1.387 (2) | C15—H15 | 0.93 |
N6—H6 | 0.86 | C16—H16 | 0.93 |
N7—C8 | 1.335 (2) | O2—C17 | 1.231 (2) |
N7—C5 | 1.380 (2) | O3—C17 | 1.254 (2) |
N7—H7 | 0.86 | O4—C19 | 1.3368 (19) |
N9—C8 | 1.315 (2) | O4—H4 | 0.82 |
N9—C4 | 1.376 (2) | N10—C22 | 1.328 (2) |
O1—C10 | 1.2198 (19) | N10—C18 | 1.344 (2) |
C2—H2 | 0.93 | N10—H10 | 0.86 |
C4—C5 | 1.402 (2) | C17—C18 | 1.509 (2) |
C5—C6 | 1.392 (2) | C18—C19 | 1.398 (2) |
C8—H8 | 0.93 | C19—C20 | 1.389 (2) |
C10—C11 | 1.493 (2) | C20—C21 | 1.374 (3) |
C11—C16 | 1.389 (2) | C20—H20 | 0.93 |
C11—C12 | 1.389 (2) | C21—C22 | 1.380 (3) |
C12—C13 | 1.383 (3) | C21—H21 | 0.93 |
C12—H12 | 0.93 | C22—H22 | 0.93 |
C6—N1—C2 | 119.09 (15) | C14—C13—H13 | 119.8 |
C2—N3—C4 | 111.76 (15) | C12—C13—H13 | 119.8 |
C10—N6—C6 | 127.30 (14) | C15—C14—C13 | 119.71 (19) |
C10—N6—H6 | 116.4 | C15—C14—H14 | 120.1 |
C6—N6—H6 | 116.4 | C13—C14—H14 | 120.1 |
C8—N7—C5 | 106.80 (14) | C14—C15—C16 | 120.48 (19) |
C8—N7—H7 | 126.6 | C14—C15—H15 | 119.8 |
C5—N7—H7 | 126.6 | C16—C15—H15 | 119.8 |
C8—N9—C4 | 104.20 (14) | C15—C16—C11 | 120.46 (18) |
N3—C2—N1 | 128.83 (16) | C15—C16—H16 | 119.8 |
N3—C2—H2 | 115.6 | C11—C16—H16 | 119.8 |
N1—C2—H2 | 115.6 | C19—O4—H4 | 109.5 |
N3—C4—N9 | 125.07 (15) | C22—N10—C18 | 123.84 (15) |
N3—C4—C5 | 124.81 (15) | C22—N10—H10 | 118.1 |
N9—C4—C5 | 110.08 (14) | C18—N10—H10 | 118.1 |
N7—C5—C6 | 137.45 (15) | O2—C17—O3 | 128.11 (16) |
N7—C5—C4 | 104.70 (14) | O2—C17—C18 | 117.88 (15) |
C6—C5—C4 | 117.69 (14) | O3—C17—C18 | 113.94 (15) |
N1—C6—N6 | 114.24 (14) | N10—C18—C19 | 118.40 (15) |
N1—C6—C5 | 117.83 (15) | N10—C18—C17 | 118.11 (15) |
N6—C6—C5 | 127.88 (15) | C19—C18—C17 | 123.47 (15) |
N9—C8—N7 | 114.21 (15) | O4—C19—C20 | 119.79 (16) |
N9—C8—H8 | 122.9 | O4—C19—C18 | 121.61 (15) |
N7—C8—H8 | 122.9 | C20—C19—C18 | 118.58 (16) |
O1—C10—N6 | 121.87 (15) | C21—C20—C19 | 120.46 (17) |
O1—C10—C11 | 121.32 (15) | C21—C20—H20 | 119.8 |
N6—C10—C11 | 116.81 (14) | C19—C20—H20 | 119.8 |
C16—C11—C12 | 118.89 (17) | C20—C21—C22 | 119.20 (16) |
C16—C11—C10 | 116.93 (15) | C20—C21—H21 | 120.4 |
C12—C11—C10 | 124.13 (15) | C22—C21—H21 | 120.4 |
C13—C12—C11 | 120.11 (18) | N10—C22—C21 | 119.39 (16) |
C13—C12—H12 | 119.9 | N10—C22—H22 | 120.3 |
C11—C12—H12 | 119.9 | C21—C22—H22 | 120.3 |
C14—C13—C12 | 120.35 (19) | ||
C4—N3—C2—N1 | −0.3 (3) | O1—C10—C11—C12 | −157.30 (18) |
C6—N1—C2—N3 | 0.5 (3) | N6—C10—C11—C12 | 21.6 (2) |
C2—N3—C4—N9 | −176.90 (16) | C16—C11—C12—C13 | 0.0 (3) |
C2—N3—C4—C5 | 0.4 (2) | C10—C11—C12—C13 | 177.27 (16) |
C8—N9—C4—N3 | 177.03 (17) | C11—C12—C13—C14 | −0.1 (3) |
C8—N9—C4—C5 | −0.59 (19) | C12—C13—C14—C15 | 0.4 (3) |
C8—N7—C5—C6 | −175.60 (19) | C13—C14—C15—C16 | −0.7 (3) |
C8—N7—C5—C4 | −0.47 (18) | C14—C15—C16—C11 | 0.6 (3) |
N3—C4—C5—N7 | −176.96 (15) | C12—C11—C16—C15 | −0.3 (3) |
N9—C4—C5—N7 | 0.67 (18) | C10—C11—C16—C15 | −177.72 (16) |
N3—C4—C5—C6 | −0.7 (3) | C22—N10—C18—C19 | −1.3 (2) |
N9—C4—C5—C6 | 176.95 (14) | C22—N10—C18—C17 | 177.12 (15) |
C2—N1—C6—N6 | 176.79 (15) | O2—C17—C18—N10 | −16.7 (3) |
C2—N1—C6—C5 | −0.7 (2) | O3—C17—C18—N10 | 165.94 (15) |
C10—N6—C6—N1 | 160.14 (16) | O2—C17—C18—C19 | 161.64 (17) |
C10—N6—C6—C5 | −22.7 (3) | O3—C17—C18—C19 | −15.8 (3) |
N7—C5—C6—N1 | 175.49 (18) | N10—C18—C19—O4 | −177.66 (14) |
C4—C5—C6—N1 | 0.8 (2) | C17—C18—C19—O4 | 4.0 (3) |
N7—C5—C6—N6 | −1.6 (3) | N10—C18—C19—C20 | 3.7 (2) |
C4—C5—C6—N6 | −176.30 (15) | C17—C18—C19—C20 | −174.59 (15) |
C4—N9—C8—N7 | 0.3 (2) | O4—C19—C20—C21 | 178.14 (15) |
C5—N7—C8—N9 | 0.1 (2) | C18—C19—C20—C21 | −3.2 (3) |
C6—N6—C10—O1 | 2.6 (3) | C19—C20—C21—C22 | 0.2 (3) |
C6—N6—C10—C11 | −176.25 (15) | C18—N10—C22—C21 | −1.8 (3) |
O1—C10—C11—C16 | 20.0 (2) | C20—C21—C22—N10 | 2.3 (3) |
N6—C10—C11—C16 | −161.15 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3 | 0.82 | 1.86 | 2.577 (2) | 146 |
O4—H4···N1 | 0.82 | 2.61 | 3.137 (2) | 123 |
N6—H6···O3 | 0.86 | 2.03 | 2.842 (2) | 158 |
N7—H7···O1 | 0.86 | 2.15 | 2.689 (2) | 121 |
N7—H7···O2i | 0.86 | 2.28 | 2.929 (2) | 132 |
N10—H10···O2 | 0.86 | 2.42 | 2.740 (2) | 102 |
N10—H10···N9ii | 0.86 | 1.88 | 2.717 (2) | 164 |
C8—H8···O2iii | 0.93 | 2.53 | 3.115 (2) | 121 |
C21—H21···O1iv | 0.93 | 2.48 | 3.384 (2) | 163 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, y−1, z; (iii) x−1, y+1, z; (iv) x+1, y, z−1. |
C12H9N5O·C4H6O6 | Z = 2 |
Mr = 389.33 | F(000) = 404 |
Triclinic, P1 | Dx = 1.562 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5844 (7) Å | Cell parameters from 2252 reflections |
b = 10.0175 (9) Å | θ = 3.4–29.9° |
c = 11.9658 (10) Å | µ = 0.13 mm−1 |
α = 111.669 (8)° | T = 293 K |
β = 93.488 (7)° | Prism, colourless |
γ = 98.845 (7)° | 0.3 × 0.15 × 0.08 mm |
V = 827.95 (14) Å3 |
Agilent SuperNova Dual Source diffractometer with Atlas detector | 3785 independent reflections |
Mirror monochromator | 2760 reflections with I > 2σ(I) |
Detector resolution: 10.4933 pixels mm-1 | Rint = 0.023 |
ω scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −8→9 |
Tmin = 0.791, Tmax = 1 | k = −12→10 |
6799 measured reflections | l = −15→15 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0504P)2 + 0.1756P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3785 reflections | Δρmax = 0.20 e Å−3 |
257 parameters | Δρmin = −0.23 e Å−3 |
C12H9N5O·C4H6O6 | γ = 98.845 (7)° |
Mr = 389.33 | V = 827.95 (14) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5844 (7) Å | Mo Kα radiation |
b = 10.0175 (9) Å | µ = 0.13 mm−1 |
c = 11.9658 (10) Å | T = 293 K |
α = 111.669 (8)° | 0.3 × 0.15 × 0.08 mm |
β = 93.488 (7)° |
Agilent SuperNova Dual Source diffractometer with Atlas detector | 3785 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | 2760 reflections with I > 2σ(I) |
Tmin = 0.791, Tmax = 1 | Rint = 0.023 |
6799 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.20 e Å−3 |
3785 reflections | Δρmin = −0.23 e Å−3 |
257 parameters |
Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.8599 (2) | −0.18858 (18) | 0.06552 (14) | 0.0376 (4) | |
N3 | 0.8873 (2) | −0.23864 (18) | 0.24560 (14) | 0.0373 (4) | |
N6 | 0.7641 (2) | 0.00673 (17) | 0.04347 (13) | 0.0347 (4) | |
H6A | 0.7844 | −0.0362 | −0.03 | 0.042* | |
N7 | 0.7389 (2) | 0.09567 (18) | 0.33263 (13) | 0.0361 (4) | |
H7 | 0.708 | 0.1712 | 0.325 | 0.043* | |
N9 | 0.7996 (2) | −0.05705 (19) | 0.42010 (14) | 0.0396 (4) | |
O1 | 0.6637 (2) | 0.20574 (16) | 0.16579 (12) | 0.0477 (4) | |
C2 | 0.8996 (3) | −0.2681 (2) | 0.12920 (17) | 0.0401 (5) | |
H2 | 0.9403 | −0.3535 | 0.0869 | 0.048* | |
C4 | 0.8305 (2) | −0.1127 (2) | 0.30113 (16) | 0.0318 (4) | |
C5 | 0.7908 (2) | −0.0190 (2) | 0.24406 (16) | 0.0311 (4) | |
C6 | 0.8036 (2) | −0.0628 (2) | 0.12100 (16) | 0.0304 (4) | |
C8 | 0.7459 (3) | 0.0666 (2) | 0.43300 (17) | 0.0429 (5) | |
H8 | 0.7156 | 0.1282 | 0.5058 | 0.051* | |
C10 | 0.6980 (2) | 0.1324 (2) | 0.06592 (16) | 0.0320 (4) | |
C11 | 0.6695 (2) | 0.1731 (2) | −0.04092 (16) | 0.0313 (4) | |
C16 | 0.6327 (3) | 0.3116 (2) | −0.01922 (18) | 0.0408 (5) | |
H16 | 0.6275 | 0.375 | 0.0597 | 0.049* | |
C15 | 0.6037 (3) | 0.3556 (2) | −0.1143 (2) | 0.0466 (5) | |
H15 | 0.5791 | 0.4484 | −0.0991 | 0.056* | |
C14 | 0.6109 (3) | 0.2632 (2) | −0.23149 (19) | 0.0429 (5) | |
H14 | 0.5912 | 0.2932 | −0.2953 | 0.051* | |
C13 | 0.6474 (3) | 0.1258 (2) | −0.25368 (17) | 0.0424 (5) | |
H13 | 0.6522 | 0.063 | −0.3328 | 0.051* | |
C12 | 0.6769 (3) | 0.0804 (2) | −0.15943 (17) | 0.0379 (4) | |
H12 | 0.7019 | −0.0124 | −0.1754 | 0.045* | |
O7 | 0.0306 (2) | 0.44846 (15) | 0.14238 (12) | 0.0462 (4) | |
O6 | 0.0213 (2) | 0.57523 (18) | 0.33864 (13) | 0.0562 (4) | |
H6 | −0.0285 | 0.6274 | 0.3132 | 0.084* | |
O5 | 0.1405 (2) | 0.22910 (15) | 0.18254 (12) | 0.0507 (4) | |
H5 | 0.1303 | 0.2497 | 0.1225 | 0.076* | |
O4 | 0.4336 (2) | 0.45284 (18) | 0.32491 (16) | 0.0585 (4) | |
H4 | 0.477 | 0.3824 | 0.2857 | 0.088* | |
O2 | 0.4639 (2) | 0.24813 (17) | 0.42002 (14) | 0.0524 (4) | |
O3 | 0.1816 (2) | 0.2378 (2) | 0.46307 (15) | 0.0580 (5) | |
H3 | 0.2078 | 0.1796 | 0.4918 | 0.087* | |
C20 | 0.0512 (3) | 0.4625 (2) | 0.24657 (17) | 0.0360 (4) | |
C19 | 0.1135 (3) | 0.3473 (2) | 0.28529 (17) | 0.0372 (4) | |
H19 | 0.0179 | 0.3106 | 0.3241 | 0.045* | |
C18 | 0.2861 (3) | 0.4056 (2) | 0.37558 (17) | 0.0396 (5) | |
H18 | 0.266 | 0.4901 | 0.4446 | 0.047* | |
C17 | 0.3227 (3) | 0.2892 (2) | 0.42276 (16) | 0.0374 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0482 (9) | 0.0387 (9) | 0.0374 (8) | 0.0232 (7) | 0.0126 (7) | 0.0208 (7) |
N3 | 0.0451 (9) | 0.0412 (10) | 0.0397 (9) | 0.0215 (7) | 0.0100 (7) | 0.0255 (7) |
N6 | 0.0481 (9) | 0.0369 (9) | 0.0300 (8) | 0.0209 (7) | 0.0097 (7) | 0.0196 (7) |
N7 | 0.0500 (9) | 0.0374 (9) | 0.0313 (8) | 0.0218 (7) | 0.0112 (7) | 0.0186 (7) |
N9 | 0.0502 (10) | 0.0471 (10) | 0.0346 (9) | 0.0216 (8) | 0.0095 (7) | 0.0251 (8) |
O1 | 0.0756 (10) | 0.0467 (9) | 0.0361 (8) | 0.0319 (7) | 0.0181 (7) | 0.0235 (7) |
C2 | 0.0512 (12) | 0.0399 (11) | 0.0414 (11) | 0.0255 (9) | 0.0131 (9) | 0.0216 (9) |
C4 | 0.0344 (9) | 0.0376 (10) | 0.0338 (9) | 0.0149 (8) | 0.0066 (7) | 0.0222 (8) |
C5 | 0.0329 (9) | 0.0351 (10) | 0.0329 (9) | 0.0121 (7) | 0.0063 (7) | 0.0192 (8) |
C6 | 0.0324 (9) | 0.0334 (10) | 0.0344 (9) | 0.0131 (7) | 0.0072 (7) | 0.0199 (8) |
C8 | 0.0595 (13) | 0.0481 (13) | 0.0319 (10) | 0.0253 (10) | 0.0113 (9) | 0.0211 (9) |
C10 | 0.0360 (9) | 0.0318 (10) | 0.0350 (9) | 0.0115 (7) | 0.0070 (7) | 0.0182 (8) |
C11 | 0.0328 (9) | 0.0344 (10) | 0.0350 (9) | 0.0093 (7) | 0.0043 (7) | 0.0218 (8) |
C16 | 0.0549 (12) | 0.0374 (11) | 0.0389 (10) | 0.0210 (9) | 0.0101 (9) | 0.0193 (9) |
C15 | 0.0600 (13) | 0.0398 (12) | 0.0558 (13) | 0.0228 (10) | 0.0123 (10) | 0.0302 (10) |
C14 | 0.0468 (11) | 0.0514 (13) | 0.0464 (12) | 0.0128 (9) | 0.0060 (9) | 0.0357 (10) |
C13 | 0.0558 (12) | 0.0453 (12) | 0.0335 (10) | 0.0120 (10) | 0.0060 (9) | 0.0225 (9) |
C12 | 0.0498 (11) | 0.0339 (10) | 0.0378 (10) | 0.0143 (8) | 0.0069 (8) | 0.0199 (8) |
O7 | 0.0693 (10) | 0.0435 (9) | 0.0361 (8) | 0.0247 (7) | 0.0059 (7) | 0.0215 (6) |
O6 | 0.0916 (12) | 0.0536 (10) | 0.0392 (8) | 0.0470 (9) | 0.0132 (8) | 0.0221 (7) |
O5 | 0.0854 (11) | 0.0339 (8) | 0.0370 (8) | 0.0264 (7) | −0.0009 (7) | 0.0139 (6) |
O4 | 0.0579 (10) | 0.0523 (10) | 0.0791 (12) | 0.0092 (8) | 0.0108 (8) | 0.0411 (9) |
O2 | 0.0552 (9) | 0.0562 (10) | 0.0603 (10) | 0.0316 (8) | 0.0134 (7) | 0.0297 (8) |
O3 | 0.0625 (10) | 0.0840 (13) | 0.0673 (10) | 0.0433 (9) | 0.0290 (8) | 0.0596 (10) |
C20 | 0.0438 (11) | 0.0336 (10) | 0.0368 (10) | 0.0164 (8) | 0.0070 (8) | 0.0167 (8) |
C19 | 0.0500 (11) | 0.0324 (10) | 0.0370 (10) | 0.0163 (8) | 0.0070 (8) | 0.0187 (8) |
C18 | 0.0507 (11) | 0.0375 (11) | 0.0351 (10) | 0.0183 (9) | 0.0029 (8) | 0.0157 (8) |
C17 | 0.0508 (11) | 0.0371 (11) | 0.0293 (9) | 0.0217 (9) | 0.0074 (8) | 0.0130 (8) |
N1—C6 | 1.339 (2) | C15—C14 | 1.375 (3) |
N1—C2 | 1.341 (2) | C15—H15 | 0.93 |
N3—C2 | 1.325 (2) | C14—C13 | 1.378 (3) |
N3—C4 | 1.342 (2) | C14—H14 | 0.93 |
N6—C10 | 1.367 (2) | C13—C12 | 1.381 (3) |
N6—C6 | 1.394 (2) | C13—H13 | 0.93 |
N6—H6A | 0.86 | C12—H12 | 0.93 |
N7—C8 | 1.336 (2) | O7—C20 | 1.199 (2) |
N7—C5 | 1.374 (2) | O6—C20 | 1.316 (2) |
N7—H7 | 0.86 | O6—H6 | 0.82 |
N9—C8 | 1.321 (3) | O5—C19 | 1.409 (2) |
N9—C4 | 1.374 (2) | O5—H5 | 0.82 |
O1—C10 | 1.218 (2) | O4—C18 | 1.405 (2) |
C2—H2 | 0.93 | O4—H4 | 0.82 |
C4—C5 | 1.405 (2) | O2—C17 | 1.202 (2) |
C5—C6 | 1.387 (2) | O3—C17 | 1.311 (2) |
C8—H8 | 0.93 | O3—H3 | 0.82 |
C10—C11 | 1.492 (2) | C20—C19 | 1.519 (3) |
C11—C12 | 1.389 (3) | C19—C18 | 1.532 (3) |
C11—C16 | 1.390 (3) | C19—H19 | 0.98 |
C16—C15 | 1.381 (3) | C18—C17 | 1.524 (3) |
C16—H16 | 0.93 | C18—H18 | 0.98 |
C6—N1—C2 | 119.63 (16) | C14—C15—H15 | 119.7 |
C2—N3—C4 | 112.97 (16) | C16—C15—H15 | 119.7 |
C10—N6—C6 | 130.14 (15) | C15—C14—C13 | 119.53 (18) |
C10—N6—H6A | 114.9 | C15—C14—H14 | 120.2 |
C6—N6—H6A | 114.9 | C13—C14—H14 | 120.2 |
C8—N7—C5 | 106.45 (16) | C14—C13—C12 | 120.57 (18) |
C8—N7—H7 | 126.8 | C14—C13—H13 | 119.7 |
C5—N7—H7 | 126.8 | C12—C13—H13 | 119.7 |
C8—N9—C4 | 104.05 (15) | C13—C12—C11 | 120.19 (18) |
N3—C2—N1 | 127.38 (18) | C13—C12—H12 | 119.9 |
N3—C2—H2 | 116.3 | C11—C12—H12 | 119.9 |
N1—C2—H2 | 116.3 | C20—O6—H6 | 109.5 |
N3—C4—N9 | 125.86 (16) | C19—O5—H5 | 109.5 |
N3—C4—C5 | 124.31 (16) | C18—O4—H4 | 109.5 |
N9—C4—C5 | 109.82 (16) | C17—O3—H3 | 109.5 |
N7—C5—C6 | 136.90 (17) | O7—C20—O6 | 124.96 (18) |
N7—C5—C4 | 105.28 (15) | O7—C20—C19 | 122.32 (17) |
C6—C5—C4 | 117.74 (16) | O6—C20—C19 | 112.71 (16) |
N1—C6—C5 | 117.90 (16) | O5—C19—C20 | 109.78 (15) |
N1—C6—N6 | 113.44 (15) | O5—C19—C18 | 109.19 (16) |
C5—C6—N6 | 128.66 (16) | C20—C19—C18 | 113.47 (16) |
N9—C8—N7 | 114.39 (17) | O5—C19—H19 | 108.1 |
N9—C8—H8 | 122.8 | C20—C19—H19 | 108.1 |
N7—C8—H8 | 122.8 | C18—C19—H19 | 108.1 |
O1—C10—N6 | 122.55 (16) | O4—C18—C17 | 111.66 (16) |
O1—C10—C11 | 122.19 (17) | O4—C18—C19 | 112.00 (16) |
N6—C10—C11 | 115.26 (15) | C17—C18—C19 | 109.58 (16) |
C12—C11—C16 | 118.91 (17) | O4—C18—H18 | 107.8 |
C12—C11—C10 | 123.65 (17) | C17—C18—H18 | 107.8 |
C16—C11—C10 | 117.44 (16) | C19—C18—H18 | 107.8 |
C15—C16—C11 | 120.26 (18) | O2—C17—O3 | 124.77 (19) |
C15—C16—H16 | 119.9 | O2—C17—C18 | 123.21 (18) |
C11—C16—H16 | 119.9 | O3—C17—C18 | 111.99 (16) |
C14—C15—C16 | 120.53 (19) | ||
C4—N3—C2—N1 | −1.0 (3) | O1—C10—C11—C12 | −168.35 (18) |
C6—N1—C2—N3 | 1.2 (3) | N6—C10—C11—C12 | 11.2 (3) |
C2—N3—C4—N9 | 177.72 (18) | O1—C10—C11—C16 | 11.3 (3) |
C2—N3—C4—C5 | −1.1 (3) | N6—C10—C11—C16 | −169.13 (16) |
C8—N9—C4—N3 | −179.86 (19) | C12—C11—C16—C15 | 0.1 (3) |
C8—N9—C4—C5 | −0.9 (2) | C10—C11—C16—C15 | −179.53 (18) |
C8—N7—C5—C6 | 175.4 (2) | C11—C16—C15—C14 | 0.0 (3) |
C8—N7—C5—C4 | −1.1 (2) | C16—C15—C14—C13 | 0.0 (3) |
N3—C4—C5—N7 | −179.76 (16) | C15—C14—C13—C12 | −0.1 (3) |
N9—C4—C5—N7 | 1.2 (2) | C14—C13—C12—C11 | 0.2 (3) |
N3—C4—C5—C6 | 2.9 (3) | C16—C11—C12—C13 | −0.2 (3) |
N9—C4—C5—C6 | −176.07 (16) | C10—C11—C12—C13 | 179.42 (17) |
C2—N1—C6—C5 | 0.8 (3) | O7—C20—C19—O5 | 0.0 (3) |
C2—N1—C6—N6 | −178.83 (16) | O6—C20—C19—O5 | 179.17 (17) |
N7—C5—C6—N1 | −178.80 (19) | O7—C20—C19—C18 | 122.5 (2) |
C4—C5—C6—N1 | −2.6 (3) | O6—C20—C19—C18 | −58.4 (2) |
N7—C5—C6—N6 | 0.7 (4) | O5—C19—C18—O4 | 59.2 (2) |
C4—C5—C6—N6 | 176.92 (17) | C20—C19—C18—O4 | −63.6 (2) |
C10—N6—C6—N1 | 177.40 (17) | O5—C19—C18—C17 | −65.30 (19) |
C10—N6—C6—C5 | −2.2 (3) | C20—C19—C18—C17 | 171.90 (15) |
C4—N9—C8—N7 | 0.2 (2) | O4—C18—C17—O2 | 2.5 (3) |
C5—N7—C8—N9 | 0.6 (2) | C19—C18—C17—O2 | 127.1 (2) |
C6—N6—C10—O1 | 0.5 (3) | O4—C18—C17—O3 | −175.90 (17) |
C6—N6—C10—C11 | −179.10 (16) | C19—C18—C17—O3 | −51.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···N3i | 0.82 | 1.97 | 2.780 (3) | 171 |
O5—H5···N1ii | 0.82 | 2.11 | 2.843 (2) | 148 |
O5—H5···O7 | 0.82 | 2.17 | 2.655 (2) | 118 |
O4—H4···O2 | 0.82 | 2.44 | 2.718 (3) | 101 |
O4—H4···O1 | 0.82 | 2.52 | 3.324 (2) | 168 |
O3—H3···N9iii | 0.82 | 1.89 | 2.679 (2) | 162 |
N6—H6A···O5ii | 0.86 | 2.29 | 3.076 (2) | 152 |
N7—H7···O1 | 0.86 | 2.07 | 2.685 (2) | 127 |
N7—H7···O2 | 0.86 | 2.32 | 2.800 (2) | 115 |
C2—H2···O7iv | 0.93 | 2.49 | 3.202 (3) | 134 |
C2—H2···O7ii | 0.93 | 2.59 | 3.205 (2) | 124 |
Symmetry codes: (i) x−1, y+1, z; (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) x+1, y−1, z. |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C12H9N5O·C6H5NO3 | C12H9N5O·C4H6O6 |
Mr | 378.35 | 389.33 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 8.3961 (4), 9.8673 (5), 11.0680 (7) | 7.5844 (7), 10.0175 (9), 11.9658 (10) |
α, β, γ (°) | 66.137 (5), 83.459 (4), 79.546 (4) | 111.669 (8), 93.488 (7), 98.845 (7) |
V (Å3) | 823.81 (8) | 827.95 (14) |
Z | 2 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.13 |
Crystal size (mm) | 0.25 × 0.2 × 0.08 | 0.3 × 0.15 × 0.08 |
Data collection | ||
Diffractometer | Agilent SuperNova Dual Source diffractometer with Atlas detector | Agilent SuperNova Dual Source diffractometer with Atlas detector |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2013) | Multi-scan (CrysAlis PRO; Agilent, 2013) |
Tmin, Tmax | 0.822, 1 | 0.791, 1 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7594, 3753, 2756 | 6799, 3785, 2760 |
Rint | 0.026 | 0.023 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.130, 1.04 | 0.047, 0.126, 1.05 |
No. of reflections | 3753 | 3785 |
No. of parameters | 253 | 257 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.22 | 0.20, −0.23 |
Computer programs: CrysAlis PRO (Agilent, 2013), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O3 | 0.82 | 1.86 | 2.577 (2) | 146 |
O4—H4···N1 | 0.82 | 2.61 | 3.137 (2) | 123 |
N6—H6···O3 | 0.86 | 2.03 | 2.842 (2) | 158 |
N7—H7···O1 | 0.86 | 2.15 | 2.689 (2) | 121 |
N7—H7···O2i | 0.86 | 2.28 | 2.929 (2) | 132 |
N10—H10···O2 | 0.86 | 2.42 | 2.740 (2) | 102 |
N10—H10···N9ii | 0.86 | 1.88 | 2.717 (2) | 164 |
C8—H8···O2iii | 0.93 | 2.53 | 3.115 (2) | 121 |
C21—H21···O1iv | 0.93 | 2.48 | 3.384 (2) | 163 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, y−1, z; (iii) x−1, y+1, z; (iv) x+1, y, z−1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···N3i | 0.82 | 1.97 | 2.780 (3) | 171 |
O5—H5···N1ii | 0.82 | 2.11 | 2.843 (2) | 148 |
O5—H5···O7 | 0.82 | 2.17 | 2.655 (2) | 118 |
O4—H4···O2 | 0.82 | 2.44 | 2.718 (3) | 101 |
O4—H4···O1 | 0.82 | 2.52 | 3.324 (2) | 168 |
O3—H3···N9iii | 0.82 | 1.89 | 2.679 (2) | 162 |
N6—H6A···O5ii | 0.86 | 2.29 | 3.076 (2) | 152 |
N7—H7···O1 | 0.86 | 2.07 | 2.685 (2) | 127 |
N7—H7···O2 | 0.86 | 2.32 | 2.800 (2) | 115 |
C2—H2···O7iv | 0.93 | 2.49 | 3.202 (3) | 134 |
C2—H2···O7ii | 0.93 | 2.59 | 3.205 (2) | 124 |
Symmetry codes: (i) x−1, y+1, z; (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) x+1, y−1, z. |
Cocrystal | Dihedral angle (°) | Torsion angle (°) | |||
Pyrimidine ring/imdazole ring of adenine (N1-N3-C2-C4-C5-C6/N7-N9-C4-C5-C8) | Purine ring/benzene ring (N1-C2-N3-C4-C5-C6-N7-C8-N9/C11-C12-C13-C14-C15-C16) | Purine ring/amide (N1-C2-N3-C4-C5-C6-N7-C8-N9/N6-H6-C10-O1) | Benzene ring/amide (C11-C12-C13-C14-C15-C16/N6-H6-C10-O1) | (C6-N6-C10-C11) | |
(I) | 3.00 (9) | 0.94 (8) | 21.20 (17) | 21.45 (18) | -176.24 (16) |
(II) | 2.26 (10) | 9.77 (8) | 2.93 (18) | 11.35 (9) | -179.08 (17) |
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