Adenosinium 3,5-di­nitro­salicyl­ate

The crystal structure of adenosinium 3,5-di­nitro­salicyl­icate, C₁₀H₁₄N₅O₄⁺·C₇H₃N₂O₇⁻, shows the presence of a primary chain structure formed through homomeric head-to-tail cyclic R₂²(10) hydrogen-bonding interactions between hydroxy O- and both purine and amine N-donor and acceptor groups of the furan­ose and purine moieties of the adenosinium species. These chain structures are related by crystallographic 2₁ symmetry. Secondary hetero-ionic hydrogen bonding, involving the 3,5-di­nitro­salicyl­ate anion, including a cyclic R₂²(8) interaction between the carboxyl­ate group and the protonated purine and amine groups of the adenosinium cation are also present, together with heteromolecular π–π interactions giving a three-dimensional hydrogen-bonded polymer structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.036
• wR factor = 0.122
• Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.59
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.49
           From the CIF: _reflns_number_total               2406
           Count of symmetry unique reflns         2405
           Completeness (_total/calc)            100.04%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SIR92 (Altomare, 1994); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.

adenosinium 3,5-dinitrosalicylate

Crystal data

C10H14N5O4^+·C7H3N2O7^−	F(000) = 512
Mr = 495.38	Dx = 1.670 Mg m^−3
Monoclinic, P21	Melting point = 487.2–488.5 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71069 Å
a = 15.297 (2) Å	Cell parameters from 25 reflections
b = 8.8543 (14) Å	θ = 12.5–16.9°
c = 7.2805 (8) Å	µ = 0.14 mm^−1
β = 92.321 (10)°	T = 298 K
V = 985.3 (2) Å^3	Plate, pale yellow
Z = 2	0.40 × 0.35 × 0.03 mm

Data collection

Rigaku AFC-7R diffractometer	1873 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.018
Graphite monochromator	θmax = 27.5°, θmin = 2.7°
ω–2θ scans	h = −8→19
Absorption correction: ψ scan (TEXSAN for Windows; Molecular Structure Corporation, 1999)	k = 0→11
Tmin = 0.945, Tmax = 0.995	l = −9→9
2690 measured reflections	3 standard reflections every 150 min
2406 independent reflections	intensity decay: 0.0%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters not refined
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 2.5029P] where P = (Fo^2 + 2Fc^2)/3
S = 0.88	(Δ/σ)max = 0.003
2406 reflections	Δρmax = 0.20 e Å^−3
317 parameters	Δρmin = −0.24 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (3)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O2	0.60981 (18)	0.1756 (4)	0.3497 (5)	0.0449 (10)
O3A	0.6826 (2)	−0.0660 (4)	0.5133 (5)	0.0530 (11)
O3B	0.8175 (2)	−0.0836 (4)	0.4380 (5)	0.0516 (11)
O5A	0.9774 (2)	0.3746 (4)	0.6546 (5)	0.0581 (11)
O5B	0.9495 (2)	0.5597 (4)	0.4672 (4)	0.0505 (10)
O7A	0.62995 (19)	0.6321 (3)	0.2930 (5)	0.0420 (9)
O7B	0.54980 (18)	0.4236 (4)	0.2720 (5)	0.0493 (10)
N3	0.7517 (2)	−0.0119 (4)	0.4699 (5)	0.0380 (10)
N5	0.9304 (2)	0.4413 (4)	0.5402 (5)	0.0380 (10)
C1	0.6965 (2)	0.3985 (4)	0.3833 (5)	0.0276 (10)
C2	0.6854 (2)	0.2404 (5)	0.3972 (5)	0.0312 (11)
C3	0.7581 (3)	0.1533 (4)	0.4576 (5)	0.0318 (11)
C4	0.8377 (3)	0.2184 (5)	0.5037 (5)	0.0337 (11)
C5	0.8454 (2)	0.3730 (5)	0.4892 (5)	0.0302 (10)
C6	0.7761 (2)	0.4645 (4)	0.4297 (5)	0.0295 (10)
C7	0.6208 (2)	0.4938 (5)	0.3118 (6)	0.0323 (11)
O21	0.70934 (18)	0.8539 (3)	1.0866 (4)	0.0360 (8)
O31	0.8179 (2)	1.0044 (3)	0.8598 (4)	0.0419 (9)
O41	0.84577 (16)	0.6698 (3)	0.7672 (4)	0.0320 (8)
O51	0.9662 (2)	0.6129 (4)	1.0694 (5)	0.0490 (10)
N12	0.5273 (2)	0.2793 (4)	0.7750 (5)	0.0348 (10)
N32	0.5874 (2)	0.5264 (4)	0.7650 (5)	0.0359 (10)
N62	0.5965 (2)	0.0651 (4)	0.8899 (5)	0.0393 (10)
N72	0.75235 (19)	0.2820 (4)	0.9702 (4)	0.0303 (9)
N92	0.73744 (19)	0.5268 (4)	0.8934 (4)	0.0285 (8)
C11	0.7654 (2)	0.6817 (4)	0.8549 (5)	0.0276 (9)
C21	0.7839 (2)	0.7775 (4)	1.0275 (5)	0.0285 (10)
C22	0.5248 (2)	0.4296 (5)	0.7334 (6)	0.0377 (11)
C31	0.8551 (2)	0.8849 (4)	0.9644 (5)	0.0306 (10)
C41	0.9063 (2)	0.7848 (4)	0.8354 (5)	0.0310 (10)
C42	0.6591 (2)	0.4599 (4)	0.8464 (5)	0.0278 (10)
C51	0.9868 (3)	0.7075 (5)	0.9208 (7)	0.0429 (14)
C52	0.6693 (2)	0.3099 (4)	0.8945 (5)	0.0289 (10)
C62	0.5992 (2)	0.2097 (4)	0.8555 (5)	0.0288 (10)
C82	0.7898 (2)	0.4153 (5)	0.9659 (6)	0.0319 (11)
H2	0.568400	0.250100	0.328000	0.0330*
H4	0.885900	0.157900	0.546000	0.0400*
H6	0.783800	0.571500	0.417800	0.0340*
H11	0.723100	0.731000	0.775300	0.0330*
H12	0.479500	0.221500	0.751400	0.0330*
H21	0.807500	0.713800	1.123300	0.0340*
H21A	0.689600	0.789700	1.173100	0.0330*
H22	0.471300	0.468100	0.676900	0.0450*
H31	0.891300	0.920600	1.065600	0.0350*
H31A	0.808700	1.090900	0.929000	0.0330*
H41	0.923100	0.844900	0.733800	0.0370*
H51A	1.028000	0.782700	0.963100	0.0540*
H51B	1.013900	0.648000	0.829000	0.0540*
H51C	0.983800	0.649000	1.164000	0.0330*
H62A	0.642600	0.026000	0.936100	0.0330*
H62B	0.553200	0.007600	0.846600	0.0330*
H82	0.849500	0.432800	1.010400	0.0380*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0298 (14)	0.0317 (15)	0.072 (2)	−0.0026 (12)	−0.0143 (13)	0.0037 (15)
O3A	0.0529 (19)	0.0355 (17)	0.070 (2)	−0.0073 (15)	−0.0059 (16)	0.0095 (16)
O3B	0.0544 (19)	0.0373 (17)	0.062 (2)	0.0159 (16)	−0.0127 (16)	−0.0100 (16)
O5A	0.0405 (16)	0.049 (2)	0.082 (2)	0.0012 (16)	−0.0312 (17)	−0.0012 (18)
O5B	0.0396 (16)	0.056 (2)	0.0559 (18)	−0.0174 (16)	0.0034 (14)	0.0052 (17)
O7A	0.0332 (14)	0.0321 (15)	0.0603 (19)	0.0047 (12)	−0.0028 (13)	0.0084 (14)
O7B	0.0291 (14)	0.0352 (16)	0.082 (2)	0.0028 (13)	−0.0187 (14)	0.0063 (17)
N3	0.0424 (18)	0.0295 (18)	0.0408 (18)	0.0044 (15)	−0.0128 (15)	−0.0019 (15)
N5	0.0273 (15)	0.040 (2)	0.0463 (19)	−0.0027 (15)	−0.0022 (13)	−0.0101 (16)
C1	0.0244 (16)	0.0275 (18)	0.0305 (17)	0.0008 (14)	−0.0022 (13)	0.0004 (14)
C2	0.0258 (17)	0.0282 (19)	0.039 (2)	0.0002 (15)	−0.0052 (14)	−0.0009 (15)
C3	0.0362 (19)	0.0261 (19)	0.0327 (18)	0.0012 (15)	−0.0041 (15)	−0.0019 (15)
C4	0.0275 (17)	0.036 (2)	0.037 (2)	0.0072 (16)	−0.0050 (15)	−0.0006 (16)
C5	0.0239 (16)	0.035 (2)	0.0316 (18)	−0.0004 (15)	−0.0017 (14)	−0.0027 (16)
C6	0.0284 (17)	0.0265 (18)	0.0332 (18)	−0.0021 (14)	−0.0033 (14)	0.0007 (15)
C7	0.0265 (17)	0.029 (2)	0.041 (2)	0.0044 (15)	−0.0029 (14)	0.0025 (16)
O21	0.0350 (13)	0.0297 (14)	0.0437 (15)	0.0050 (12)	0.0047 (12)	0.0019 (12)
O31	0.0592 (18)	0.0221 (14)	0.0441 (15)	0.0053 (14)	−0.0022 (13)	0.0014 (13)
O41	0.0267 (12)	0.0295 (13)	0.0398 (14)	−0.0051 (11)	0.0026 (10)	−0.0076 (12)
O51	0.0490 (17)	0.0401 (18)	0.0561 (18)	0.0072 (15)	−0.0186 (14)	0.0025 (15)
N12	0.0241 (14)	0.0270 (16)	0.0528 (19)	−0.0031 (13)	−0.0063 (13)	−0.0015 (15)
N32	0.0261 (15)	0.0299 (17)	0.051 (2)	0.0011 (13)	−0.0073 (13)	0.0040 (15)
N62	0.0280 (16)	0.0289 (17)	0.060 (2)	−0.0053 (14)	−0.0111 (15)	−0.0030 (16)
N72	0.0269 (14)	0.0246 (15)	0.0388 (16)	0.0020 (13)	−0.0075 (12)	−0.0024 (13)
N92	0.0240 (14)	0.0221 (14)	0.0391 (16)	0.0011 (12)	−0.0025 (12)	−0.0015 (13)
C11	0.0241 (15)	0.0246 (17)	0.0339 (17)	0.0013 (14)	−0.0027 (13)	−0.0006 (15)
C21	0.0284 (17)	0.0241 (17)	0.0327 (17)	0.0029 (15)	−0.0020 (13)	0.0014 (15)
C22	0.0272 (18)	0.0280 (19)	0.057 (2)	0.0040 (16)	−0.0078 (16)	0.0013 (18)
C31	0.0311 (17)	0.0235 (17)	0.0367 (18)	−0.0055 (14)	−0.0056 (14)	−0.0038 (15)
C41	0.0282 (17)	0.0240 (17)	0.0407 (19)	−0.0071 (15)	0.0012 (14)	0.0005 (16)
C42	0.0237 (15)	0.0260 (18)	0.0336 (17)	0.0011 (14)	−0.0009 (13)	−0.0027 (14)
C51	0.0281 (19)	0.037 (2)	0.063 (3)	−0.0012 (17)	−0.0074 (17)	−0.002 (2)
C52	0.0249 (16)	0.0237 (18)	0.0380 (18)	−0.0006 (14)	−0.0001 (14)	−0.0018 (15)
C62	0.0264 (17)	0.0233 (18)	0.0364 (18)	−0.0001 (14)	−0.0014 (14)	−0.0043 (15)
C82	0.0268 (17)	0.0275 (18)	0.041 (2)	0.0029 (15)	−0.0049 (14)	0.0008 (16)

Geometric parameters (Å, º)

O2—C2	1.324 (5)	N92—C11	1.467 (5)
O3A—N3	1.214 (5)	N12—H12	0.9033
O3B—N3	1.220 (5)	N62—H62B	0.8834
O5A—N5	1.229 (5)	N62—H62A	0.8433
O5B—N5	1.216 (5)	C1—C2	1.414 (6)
O7A—C7	1.241 (5)	C1—C7	1.508 (5)
O7B—C7	1.275 (5)	C1—C6	1.380 (5)
O2—H2	0.9237	C2—C3	1.409 (6)
O21—C21	1.408 (4)	C3—C4	1.376 (6)
O31—C31	1.410 (4)	C4—C5	1.378 (6)
O41—C11	1.412 (4)	C5—C6	1.389 (5)
O41—C41	1.450 (4)	C4—H4	0.9524
O51—C51	1.414 (6)	C6—H6	0.9591
O21—H21A	0.9090	C11—C21	1.533 (5)
O31—H31A	0.9306	C21—C31	1.530 (5)
O51—H51C	0.7962	C31—C41	1.530 (5)
N3—C3	1.469 (5)	C41—C51	1.520 (6)
N5—C5	1.468 (5)	C42—C52	1.381 (5)
N12—C62	1.371 (5)	C52—C62	1.412 (5)
N12—C22	1.365 (6)	C11—H11	0.9564
N32—C42	1.359 (5)	C21—H21	0.9563
N32—C22	1.299 (5)	C22—H22	0.9633
N62—C62	1.306 (5)	C31—H31	0.9573
N72—C52	1.386 (4)	C41—H41	0.9549
N72—C82	1.313 (5)	C51—H51A	0.9590
N92—C42	1.368 (4)	C51—H51B	0.9584
N92—C82	1.364 (5)	C82—H82	0.9690
C2—O2—H2	108.71	N72—C52—C62	130.1 (3)
C11—O41—C41	110.4 (3)	C42—C52—C62	118.4 (3)
C21—O21—H21A	101.96	N72—C52—C42	111.4 (3)
C31—O31—H31A	113.07	N12—C62—N62	119.4 (3)
C51—O51—H51C	110.00	N62—C62—C52	127.4 (3)
O3B—N3—C3	116.7 (3)	N12—C62—C52	113.1 (3)
O3A—N3—C3	118.0 (3)	N72—C82—N92	114.2 (3)
O3A—N3—O3B	125.3 (4)	O41—C11—H11	109.89
O5B—N5—C5	118.1 (3)	N92—C11—H11	110.31
O5A—N5—O5B	124.5 (3)	C21—C11—H11	110.00
O5A—N5—C5	117.5 (3)	O21—C21—H21	110.30
C22—N12—C62	123.2 (3)	C11—C21—H21	108.86
C22—N32—C42	111.6 (3)	C31—C21—H21	109.46
C52—N72—C82	102.9 (3)	N12—C22—H22	117.09
C11—N92—C82	125.4 (3)	N32—C22—H22	116.72
C11—N92—C42	128.0 (3)	O31—C31—H31	112.09
C42—N92—C82	106.1 (3)	C21—C31—H31	111.76
O21—C21—C11	113.0 (3)	C41—C31—H31	111.67
N12—C22—N32	126.2 (3)	O41—C41—H41	108.31
O31—C31—C21	110.6 (3)	C31—C41—H41	108.25
O31—C31—C41	108.0 (3)	C51—C41—H41	109.20
C21—C31—C41	102.3 (3)	O51—C51—H51A	109.24
O41—C41—C31	106.3 (2)	O51—C51—H51B	108.91
O41—C41—C51	108.6 (3)	C41—C51—H51A	109.26
C31—C41—C51	115.9 (3)	C41—C51—H51B	109.18
N32—C42—N92	127.2 (3)	H51A—C51—H51B	107.96
N32—C42—C52	127.4 (3)	N72—C82—H82	122.82
N92—C42—C52	105.3 (3)	N92—C82—H82	122.98
O51—C51—C41	112.2 (4)
C41—O41—C11—C21	−17.4 (4)	C7—C1—C2—O2	−0.4 (5)
C11—O41—C41—C31	−5.4 (4)	C7—C1—C2—C3	177.6 (3)
C41—O41—C11—N92	−139.1 (3)	C7—C1—C6—C5	−177.8 (3)
C11—O41—C41—C51	119.9 (3)	C2—C1—C7—O7B	1.6 (5)
O3B—N3—C3—C4	−32.0 (5)	O2—C2—C3—C4	178.6 (4)
O3A—N3—C3—C2	−34.3 (5)	O2—C2—C3—N3	−0.2 (6)
O3B—N3—C3—C2	146.8 (4)	C1—C2—C3—N3	−178.2 (3)
O3A—N3—C3—C4	146.9 (4)	C1—C2—C3—C4	0.6 (5)
O5A—N5—C5—C4	−27.6 (5)	N3—C3—C4—C5	178.6 (3)
O5A—N5—C5—C6	152.0 (4)	C2—C3—C4—C5	−0.1 (6)
O5B—N5—C5—C4	152.6 (4)	C3—C4—C5—C6	−0.1 (6)
O5B—N5—C5—C6	−27.8 (5)	C3—C4—C5—N5	179.5 (4)
C62—N12—C22—N32	−1.0 (7)	C4—C5—C6—C1	0.0 (6)
C22—N12—C62—C52	1.4 (5)	N5—C5—C6—C1	−179.6 (3)
C22—N12—C62—N62	−179.6 (4)	N92—C11—C21—O21	−89.0 (3)
C42—N32—C22—N12	0.4 (6)	O41—C11—C21—C31	32.8 (3)
C22—N32—C42—C52	−0.2 (6)	O41—C11—C21—O21	154.2 (3)
C22—N32—C42—N92	177.8 (4)	N92—C11—C21—C31	149.5 (3)
C82—N72—C52—C62	177.2 (4)	O21—C21—C31—O31	−41.5 (4)
C52—N72—C82—N92	0.0 (4)	O21—C21—C31—C41	−156.3 (3)
C82—N72—C52—C42	0.1 (4)	C11—C21—C31—C41	−34.7 (3)
C11—N92—C42—C52	173.1 (3)	C11—C21—C31—O31	80.1 (3)
C82—N92—C11—C21	−71.4 (4)	O31—C31—C41—C51	148.1 (3)
C11—N92—C42—N32	−5.3 (6)	O31—C31—C41—O41	−91.1 (3)
C42—N92—C11—C21	116.9 (4)	C21—C31—C41—O41	25.6 (3)
C82—N92—C42—N32	−178.3 (4)	C21—C31—C41—C51	−95.2 (3)
C42—N92—C11—O41	−126.6 (3)	O41—C41—C51—O51	−60.4 (4)
C82—N92—C42—C52	0.1 (4)	C31—C41—C51—O51	59.2 (5)
C11—N92—C82—N72	−173.3 (3)	N92—C42—C52—C62	−177.6 (3)
C42—N92—C82—N72	0.0 (4)	N92—C42—C52—N72	−0.1 (4)
C82—N92—C11—O41	45.2 (5)	N32—C42—C52—N72	178.3 (4)
C6—C1—C2—O2	−178.7 (4)	N32—C42—C52—C62	0.7 (6)
C6—C1—C2—C3	−0.7 (5)	N72—C52—C62—N62	2.8 (7)
C6—C1—C7—O7A	0.6 (6)	C42—C52—C62—N12	−1.2 (5)
C6—C1—C7—O7B	179.9 (5)	C42—C52—C62—N62	179.9 (5)
C2—C1—C7—O7A	−177.7 (4)	N72—C52—C62—N12	−178.2 (4)
C2—C1—C6—C5	0.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O7B	0.92	1.61	2.438 (5)	147
N12—H12···O7A^i	0.90	1.87	2.763 (4)	170
N62—H62B···O7B^i	0.88	1.92	2.785 (5)	167
O21—H21A···O7A^ii	0.91	1.90	2.782 (4)	163
O51—H51C···O5B^ii	0.80	2.42	2.955 (5)	125
O31—H31A···N72^iii	0.93	1.93	2.785 (4)	152
O51—H51C···O5A^iv	0.80	2.45	3.164 (5)	149
N62—H62A···O21^v	0.84	2.12	2.886 (4)	152
C22—H22···O2^vi	0.96	2.22	3.041 (5)	142
C82—H82···O51	0.97	2.42	3.278 (5)	148

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x, y, z+1; (iii) x, y+1, z; (iv) −x+2, y+1/2, −z+2; (v) x, y−1, z; (vi) −x+1, y+1/2, −z+1.