Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052087/fj2052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052087/fj2052Isup2.hkl |
CCDC reference: 667439
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.089
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H6 .. H7 .. 2.06 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C1 -C3_a 1.45 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C3_a ... 1.54 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related compounds, see: Gotoh et al. (2006); Jai-nhuknan et al. (1997); Ojala et al. (1994); Young et al. (1991).
Crystals were obtained by slow evaporation from a methanol solution (100 ml) of chloranilic acid with adenine in a 1:2 molar ratio (37 and 48 mg for chloranilic acid and adenine, respectively).
H atoms were found in a difference Fourier map and refined isotropically [refined distances: O—H = 0.85 (3)–0.94 (3), N—H = 0.88 (2)–0.90 (2) and C—H = 0.939 (19)–0.965 (19) Å].
The title compound, (I), was prepared in order to extend our studies on D—H···A hydrogen bonding (D = N, O, or C; A = N, O or Cl) in the pyridine–chloranilic acid system (Gotoh et al., 2006). Adenine, one of the nucleotide building blocks, is a strong base and some crystal structures of its organic salts have been reported (Jai-Nhuknan et al., 1997; Ojala et al., 1994; Young et al., 1991).
The asymmetric unit in (I) contains one adeninium cation, one half chloranilate dianion and a water molecule; these three molecules are held together by O3—H7···O1, N1—H1···O1, N5—H6···O3, O3—H7···Cl1 and C5—H2···O2i hydrogen bonds (Table 1), forming a centrosymmetric unit (Fig. 1). The neighboring units related by an inversion center are connected by an N5—H5···N4iii hydrogen bond (Table 1), resulting in an approximately planar tape running along the [210] direction (Fig. 2). The tapes are further connected by N3—H3···Cl1ii, N3—H3···O2ii and O3—H8···N2iv hydrogen bonds (Table 1), forming a three-dimensional hydrogen-bond network.
For related compounds, see: Gotoh et al. (2006); Jai-nhuknan et al. (1997); Ojala et al. (1994); Young et al. (1991).
Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO (Rigaku/MSC, 2004); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).
2C5N5H6+·C6Cl2O42−·2H2O | F(000) = 528.00 |
Mr = 515.27 | Dx = 1.736 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 12221 reflections |
a = 7.7080 (4) Å | θ = 3.1–30.1° |
b = 7.1460 (3) Å | µ = 0.39 mm−1 |
c = 17.9718 (9) Å | T = 100 K |
β = 95.366 (2)° | Plate, purple |
V = 985.57 (8) Å3 | 0.30 × 0.25 × 0.13 mm |
Z = 2 |
Rigaku R-AXIS RAPID-II diffractometer | 2560 reflections with I > 2σ(I) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.058 |
ω scans | θmax = 30.0°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −10→10 |
Tmin = 0.854, Tmax = 0.950 | k = −10→9 |
10874 measured reflections | l = −25→24 |
2876 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0471P)2 + 0.5544P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.089 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.39 e Å−3 |
2876 reflections | Δρmin = −0.37 e Å−3 |
186 parameters |
2C5N5H6+·C6Cl2O42−·2H2O | V = 985.57 (8) Å3 |
Mr = 515.27 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.7080 (4) Å | µ = 0.39 mm−1 |
b = 7.1460 (3) Å | T = 100 K |
c = 17.9718 (9) Å | 0.30 × 0.25 × 0.13 mm |
β = 95.366 (2)° |
Rigaku R-AXIS RAPID-II diffractometer | 2876 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2560 reflections with I > 2σ(I) |
Tmin = 0.854, Tmax = 0.950 | Rint = 0.058 |
10874 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.089 | All H-atom parameters refined |
S = 1.08 | Δρmax = 0.39 e Å−3 |
2876 reflections | Δρmin = −0.37 e Å−3 |
186 parameters |
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 | ||
Cl1 | 0.19323 (4) | 0.42773 (4) | 0.660836 (15) | 0.01354 (9) | |
O1 | 0.32479 (12) | 0.34900 (15) | 0.51288 (5) | 0.0162 (2) | |
O2 | −0.16665 (12) | 0.57064 (14) | 0.62314 (5) | 0.01537 (19) | |
O3 | 0.54421 (14) | 0.20531 (15) | 0.62976 (6) | 0.0187 (2) | |
N1 | 0.53807 (15) | 0.21786 (16) | 0.40694 (6) | 0.0140 (2) | |
N2 | 0.59010 (15) | 0.16074 (16) | 0.28044 (6) | 0.0152 (2) | |
N3 | 0.87954 (15) | 0.02622 (16) | 0.27282 (6) | 0.0138 (2) | |
N4 | 0.97050 (14) | 0.00942 (16) | 0.39558 (6) | 0.0137 (2) | |
N5 | 0.73247 (16) | 0.13676 (17) | 0.51095 (6) | 0.0155 (2) | |
C1 | 0.17542 (16) | 0.41976 (17) | 0.50991 (7) | 0.0115 (2) | |
C2 | 0.08698 (16) | 0.46508 (18) | 0.57219 (6) | 0.0115 (2) | |
C3 | −0.08301 (16) | 0.53768 (17) | 0.56819 (7) | 0.0113 (2) | |
C4 | 0.69243 (16) | 0.14470 (18) | 0.43820 (7) | 0.0126 (2) | |
C5 | 0.49359 (17) | 0.2210 (2) | 0.33161 (7) | 0.0160 (2) | |
C6 | 0.74616 (17) | 0.09277 (18) | 0.31014 (7) | 0.0125 (2) | |
C7 | 1.00994 (17) | −0.02156 (19) | 0.32668 (7) | 0.0149 (2) | |
C8 | 0.80350 (16) | 0.08175 (17) | 0.38542 (7) | 0.0122 (2) | |
H1 | 0.462 (3) | 0.269 (3) | 0.4356 (12) | 0.029 (5)* | |
H2 | 0.384 (2) | 0.273 (3) | 0.3169 (10) | 0.016 (4)* | |
H3 | 0.876 (3) | 0.011 (3) | 0.2228 (13) | 0.032 (5)* | |
H4 | 1.120 (3) | −0.071 (3) | 0.3134 (11) | 0.019 (4)* | |
H5 | 0.833 (3) | 0.085 (3) | 0.5277 (12) | 0.025 (5)* | |
H6 | 0.661 (3) | 0.182 (3) | 0.5434 (14) | 0.038 (6)* | |
H7 | 0.461 (4) | 0.262 (4) | 0.6051 (16) | 0.055 (8)* | |
H8 | 0.553 (3) | 0.256 (4) | 0.6781 (17) | 0.056 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01460 (15) | 0.01792 (15) | 0.00795 (13) | 0.00072 (11) | 0.00021 (9) | 0.00064 (10) |
O1 | 0.0136 (4) | 0.0241 (5) | 0.0110 (4) | 0.0042 (4) | 0.0015 (3) | 0.0002 (4) |
O2 | 0.0157 (4) | 0.0209 (5) | 0.0100 (4) | 0.0019 (4) | 0.0040 (3) | 0.0002 (4) |
O3 | 0.0187 (5) | 0.0243 (5) | 0.0133 (4) | 0.0044 (4) | 0.0019 (4) | −0.0020 (4) |
N1 | 0.0141 (5) | 0.0159 (5) | 0.0123 (5) | 0.0024 (4) | 0.0028 (4) | −0.0011 (4) |
N2 | 0.0159 (5) | 0.0178 (5) | 0.0119 (5) | 0.0003 (4) | 0.0007 (4) | 0.0000 (4) |
N3 | 0.0160 (5) | 0.0163 (5) | 0.0095 (4) | −0.0004 (4) | 0.0026 (4) | −0.0003 (4) |
N4 | 0.0135 (5) | 0.0153 (5) | 0.0123 (5) | 0.0000 (4) | 0.0017 (4) | 0.0000 (4) |
N5 | 0.0165 (5) | 0.0208 (5) | 0.0094 (5) | 0.0020 (4) | 0.0023 (4) | −0.0005 (4) |
C1 | 0.0132 (5) | 0.0126 (5) | 0.0089 (5) | −0.0014 (4) | 0.0018 (4) | 0.0000 (4) |
C2 | 0.0138 (5) | 0.0138 (5) | 0.0069 (5) | −0.0007 (4) | 0.0003 (4) | 0.0004 (4) |
C3 | 0.0133 (5) | 0.0116 (5) | 0.0091 (5) | −0.0020 (4) | 0.0013 (4) | −0.0001 (4) |
C4 | 0.0135 (5) | 0.0128 (5) | 0.0115 (5) | −0.0016 (4) | 0.0014 (4) | −0.0005 (4) |
C5 | 0.0152 (6) | 0.0187 (6) | 0.0137 (5) | 0.0014 (5) | −0.0004 (4) | 0.0007 (5) |
C6 | 0.0151 (5) | 0.0129 (5) | 0.0100 (5) | −0.0016 (4) | 0.0029 (4) | −0.0006 (4) |
C7 | 0.0155 (6) | 0.0170 (6) | 0.0123 (5) | −0.0003 (5) | 0.0024 (4) | −0.0004 (5) |
C8 | 0.0135 (5) | 0.0133 (5) | 0.0098 (5) | −0.0009 (4) | 0.0009 (4) | −0.0002 (4) |
Cl1—C2 | 1.7423 (12) | N4—C7 | 1.3210 (17) |
O1—C1 | 1.2540 (15) | N4—C8 | 1.3833 (16) |
O2—C3 | 1.2512 (15) | N5—C4 | 1.3163 (16) |
O3—H7 | 0.85 (3) | N5—H5 | 0.88 (2) |
O3—H8 | 0.94 (3) | N5—H6 | 0.90 (2) |
N1—C5 | 1.3653 (17) | C1—C2 | 1.4019 (16) |
N1—C4 | 1.3709 (17) | C1—C3i | 1.5437 (17) |
N1—H1 | 0.90 (2) | C2—C3 | 1.4049 (17) |
N2—C5 | 1.3085 (17) | C3—C1i | 1.5437 (17) |
N2—C6 | 1.3593 (17) | C4—C8 | 1.4096 (17) |
N3—C6 | 1.3645 (16) | C5—H2 | 0.939 (19) |
N3—C7 | 1.3718 (17) | C6—C8 | 1.3857 (17) |
N3—H3 | 0.90 (2) | C7—H4 | 0.965 (19) |
H7—O3—H8 | 106 (2) | O2—C3—C2 | 125.17 (11) |
C5—N1—C4 | 122.71 (11) | O2—C3—C1i | 116.91 (11) |
C5—N1—H1 | 116.5 (14) | C2—C3—C1i | 117.92 (10) |
C4—N1—H1 | 120.8 (14) | N5—C4—N1 | 122.51 (12) |
C5—N2—C6 | 112.45 (11) | N5—C4—C8 | 123.64 (12) |
C6—N3—C7 | 106.02 (11) | N1—C4—C8 | 113.85 (11) |
C6—N3—H3 | 125.2 (14) | N2—C5—N1 | 125.80 (12) |
C7—N3—H3 | 128.7 (14) | N2—C5—H2 | 119.2 (11) |
C7—N4—C8 | 103.40 (11) | N1—C5—H2 | 115.0 (11) |
C4—N5—H5 | 118.1 (14) | N2—C6—N3 | 127.68 (11) |
C4—N5—H6 | 121.8 (15) | N2—C6—C8 | 126.40 (12) |
H5—N5—H6 | 120 (2) | N3—C6—C8 | 105.90 (11) |
O1—C1—C2 | 124.90 (11) | N4—C7—N3 | 113.70 (12) |
O1—C1—C3i | 117.51 (10) | N4—C7—H4 | 125.2 (12) |
C2—C1—C3i | 117.58 (11) | N3—C7—H4 | 121.1 (12) |
C1—C2—C3 | 124.42 (11) | N4—C8—C6 | 110.98 (11) |
C1—C2—Cl1 | 118.20 (9) | N4—C8—C4 | 130.29 (12) |
C3—C2—Cl1 | 117.37 (9) | C6—C8—C4 | 118.72 (12) |
O1—C1—C2—C3 | −177.45 (13) | C7—N3—C6—N2 | 178.54 (13) |
C3i—C1—C2—C3 | 3.3 (2) | C7—N3—C6—C8 | 0.03 (14) |
O1—C1—C2—Cl1 | 2.04 (18) | C8—N4—C7—N3 | 0.08 (15) |
C3i—C1—C2—Cl1 | −177.18 (9) | C6—N3—C7—N4 | −0.07 (16) |
C1—C2—C3—O2 | 176.49 (12) | C7—N4—C8—C6 | −0.05 (15) |
Cl1—C2—C3—O2 | −3.01 (18) | C7—N4—C8—C4 | −178.86 (13) |
C1—C2—C3—C1i | −3.3 (2) | N2—C6—C8—N4 | −178.52 (12) |
Cl1—C2—C3—C1i | 177.16 (9) | N3—C6—C8—N4 | 0.01 (14) |
C5—N1—C4—N5 | −177.86 (13) | N2—C6—C8—C4 | 0.4 (2) |
C5—N1—C4—C8 | 2.88 (18) | N3—C6—C8—C4 | 178.97 (11) |
C6—N2—C5—N1 | −0.4 (2) | N5—C4—C8—N4 | −2.8 (2) |
C4—N1—C5—N2 | −1.6 (2) | N1—C4—C8—N4 | 176.46 (13) |
C5—N2—C6—N3 | −177.25 (13) | N5—C4—C8—C6 | 178.47 (12) |
C5—N2—C6—C8 | 0.96 (19) | N1—C4—C8—C6 | −2.27 (17) |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H2···O2i | 0.938 (17) | 2.357 (17) | 3.1004 (16) | 136.0 (15) |
N1—H1···O1 | 0.89 (2) | 1.91 (2) | 2.7913 (15) | 168 (2) |
N3—H3···Cl1ii | 0.90 (2) | 2.81 (2) | 3.3038 (12) | 115.4 (17) |
N3—H3···O2ii | 0.90 (2) | 1.88 (2) | 2.7682 (14) | 166 (2) |
N5—H5···N4iii | 0.89 (2) | 2.06 (2) | 2.9044 (16) | 158 (2) |
N5—H6···O3 | 0.90 (2) | 1.87 (2) | 2.7358 (16) | 160 (2) |
O3—H7···Cl1 | 0.85 (3) | 2.66 (3) | 3.2311 (11) | 126 (2) |
O3—H7···O1 | 0.85 (3) | 1.98 (3) | 2.7681 (14) | 155 (3) |
O3—H8···N2iv | 0.94 (3) | 1.93 (3) | 2.8628 (15) | 174 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, −y+1/2, z−1/2; (iii) −x+2, −y, −z+1; (iv) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | 2C5N5H6+·C6Cl2O42−·2H2O |
Mr | 515.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 7.7080 (4), 7.1460 (3), 17.9718 (9) |
β (°) | 95.366 (2) |
V (Å3) | 985.57 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.39 |
Crystal size (mm) | 0.30 × 0.25 × 0.13 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID-II |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.854, 0.950 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10874, 2876, 2560 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.089, 1.08 |
No. of reflections | 2876 |
No. of parameters | 186 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.39, −0.37 |
Computer programs: PROCESS-AUTO (Rigaku/MSC, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H2···O2i | 0.938 (17) | 2.357 (17) | 3.1004 (16) | 136.0 (15) |
N1—H1···O1 | 0.89 (2) | 1.91 (2) | 2.7913 (15) | 168 (2) |
N3—H3···Cl1ii | 0.90 (2) | 2.81 (2) | 3.3038 (12) | 115.4 (17) |
N3—H3···O2ii | 0.90 (2) | 1.88 (2) | 2.7682 (14) | 166 (2) |
N5—H5···N4iii | 0.89 (2) | 2.06 (2) | 2.9044 (16) | 158 (2) |
N5—H6···O3 | 0.90 (2) | 1.87 (2) | 2.7358 (16) | 160 (2) |
O3—H7···Cl1 | 0.85 (3) | 2.66 (3) | 3.2311 (11) | 126 (2) |
O3—H7···O1 | 0.85 (3) | 1.98 (3) | 2.7681 (14) | 155 (3) |
O3—H8···N2iv | 0.94 (3) | 1.93 (3) | 2.8628 (15) | 174 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x+1, −y+1/2, z−1/2; (iii) −x+2, −y, −z+1; (iv) x, −y+1/2, z+1/2. |
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The title compound, (I), was prepared in order to extend our studies on D—H···A hydrogen bonding (D = N, O, or C; A = N, O or Cl) in the pyridine–chloranilic acid system (Gotoh et al., 2006). Adenine, one of the nucleotide building blocks, is a strong base and some crystal structures of its organic salts have been reported (Jai-Nhuknan et al., 1997; Ojala et al., 1994; Young et al., 1991).
The asymmetric unit in (I) contains one adeninium cation, one half chloranilate dianion and a water molecule; these three molecules are held together by O3—H7···O1, N1—H1···O1, N5—H6···O3, O3—H7···Cl1 and C5—H2···O2i hydrogen bonds (Table 1), forming a centrosymmetric unit (Fig. 1). The neighboring units related by an inversion center are connected by an N5—H5···N4iii hydrogen bond (Table 1), resulting in an approximately planar tape running along the [210] direction (Fig. 2). The tapes are further connected by N3—H3···Cl1ii, N3—H3···O2ii and O3—H8···N2iv hydrogen bonds (Table 1), forming a three-dimensional hydrogen-bond network.