Literature DB >> 21588028

2-Amino-pyridinium picrate.

M S Sivaramkumar, R Velmurugan, M Sekar, P Ramesh, M N Ponnuswamy.   

Abstract

In the title compound, C(5)H(7)N(2) (+)·C(6)n class="Species">H(2)N(3)O(7) (-), there are two crystallographically independent cations and anions (A and B) in the asymmetric unit. In both picrate anions, one of the nitro groups lies in the plane of the benzene ring [r.m.s. deviations = 0.014 (2) and 0.014 (2) Å for anions A and B, respectively] and the other two are twisted away by 39.0 (2) and 18.8 (2)° in A, and 18.2 (1) and 2.5 (2)° in B. In the crystal, the cations and anions are linked by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds, forming a two-dimensional network.

Entities:  

Year:  2010        PMID： 21588028      PMCID： PMC3006739          DOI： 10.1107/S1600536810024220

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background to picrate complexes, see: In et al. (1997 ▶); Zaderenko et al. (1997 ▶).

Experimental

Crystal data

C5H7N2 +·C6n class="Species">H2N3O7 − M = 323.23 Triclinic, a = 11.2543 (4) Å b = 11.6588 (5) Å c = 12.9883 (5) Å α = 114.641 (4)° β = 100.204 (3)° γ = 103.928 (3)° V = 1427.16 (12) Å3 Z = 4 Mo Kα radiation μ = 0.13 mm−1 T = 110 K 0.20 × 0.17 × 0.15 mm

Data collection

Bruker SMART APEXII area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.975, T max = 0.981 12905 measured reflections 6555 independent reflections 3011 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.054 wR(F 2) = 0.179 S = 0.90 6555 reflections 438 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.27 e Å−3 Δρmin = −0.21 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024220/sj5016sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024220/sj5016Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C5H7N2+·C6H2N3O7−Z = 4
Mr = 323.23F(000) = 664
Triclinic, P1Dx = 1.504 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.2543 (4) ÅCell parameters from 1241 reflections
b = 11.6588 (5) Åθ = 2.9–29.2°
c = 12.9883 (5) ŵ = 0.13 mm−1
α = 114.641 (4)°T = 110 K
β = 100.204 (3)°Block, colourless
γ = 103.928 (3)°0.20 × 0.17 × 0.15 mm
V = 1427.16 (12) Å3
Bruker SMART APEXII area-detector diffractometer6555 independent reflections
Radiation source: fine-focus sealed tube3011 reflections with I > 2σ(I)
graphiteRint = 0.020
ω and φ scansθmax = 29.2°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −14→14
Tmin = 0.975, Tmax = 0.981k = −13→15
12905 measured reflectionsl = −17→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H atoms treated by a mixture of independent and constrained refinement
S = 0.90w = 1/[σ2(Fo2) + (0.0994P)2] where P = (Fo2 + 2Fc2)/3
6555 reflections(Δ/σ)max = 0.003
438 parametersΔρmax = 0.27 e Å−3
1 restraintΔρmin = −0.21 e Å−3
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.
xyzUiso*/Ueq
O1A0.09943 (15)0.43819 (16)0.43463 (15)0.0536 (5)
O1B0.23913 (17)0.3169 (2)0.1731 (2)0.0813 (7)
O2A0.27377 (16)0.3677 (2)0.54622 (19)0.0748 (6)
O2B0.40164 (17)0.3168 (2)0.3449 (2)0.0836 (7)
O3A0.20270 (17)0.33859 (19)0.67855 (17)0.0710 (6)
O3B0.36036 (19)0.1314 (2)0.3494 (2)0.0942 (8)
O4A−0.20594 (19)−0.04375 (18)0.48852 (19)0.0745 (6)
O4B−0.0709 (2)−0.1479 (2)0.2427 (2)0.0963 (8)
O5A−0.35954 (18)−0.03632 (19)0.36907 (19)0.0752 (6)
O5B−0.2227 (2)−0.1377 (2)0.1262 (2)0.1038 (9)
O6A−0.28300 (19)0.3105 (3)0.2612 (2)0.1067 (9)
O6B−0.14349 (18)0.1761 (2)−0.0134 (2)0.0871 (7)
O7A−0.09658 (17)0.40685 (19)0.26526 (17)0.0671 (6)
O7B0.03844 (19)0.3203 (2)0.0375 (2)0.0870 (7)
N1A0.17461 (19)0.6011 (2)0.33902 (18)0.0435 (5)
H1A0.124 (2)0.534 (3)0.342 (2)0.061 (8)*
N1B0.31598 (19)0.4800 (2)0.08244 (18)0.0478 (5)
H1B0.265 (2)0.409 (3)0.093 (2)0.070 (8)*
C2A0.1199 (3)0.6384 (3)0.2628 (2)0.0538 (7)
H2A0.03060.59450.21900.065*
C2B0.2668 (3)0.5098 (3)−0.0024 (3)0.0631 (8)
H2B0.17910.4623−0.05080.076*
C3A0.1918 (3)0.7381 (3)0.2486 (3)0.0637 (8)
H3A0.15420.76420.19440.076*
C3B0.3409 (3)0.6061 (3)−0.0190 (3)0.0681 (8)
H3B0.30690.6277−0.07810.082*
C4A0.3221 (3)0.8020 (3)0.3147 (3)0.0616 (8)
H4A0.37360.87270.30570.074*
C4B0.4689 (3)0.6726 (3)0.0531 (3)0.0621 (8)
H4B0.52300.74040.04270.075*
C5A0.3761 (3)0.7650 (2)0.3913 (2)0.0556 (7)
H5A0.46500.80960.43640.067*
C5B0.5183 (2)0.6432 (2)0.1379 (2)0.0527 (7)
H5B0.60590.69050.18650.063*
C6A0.2995 (2)0.6592 (2)0.4042 (2)0.0417 (6)
C6B0.4402 (2)0.5433 (2)0.1535 (2)0.0425 (6)
N7A0.3450 (2)0.6145 (2)0.4761 (2)0.0557 (6)
H7A0.427 (3)0.650 (3)0.514 (3)0.102 (8)*
H7B0.287 (3)0.528 (3)0.474 (3)0.102 (8)*
N7B0.4794 (3)0.5063 (3)0.2321 (2)0.0626 (7)
H7C0.547 (3)0.539 (3)0.265 (3)0.060 (10)*
H7D0.423 (3)0.450 (3)0.239 (3)0.070 (10)*
C8A0.0194 (2)0.3402 (2)0.43135 (19)0.0361 (5)
C8B0.1588 (2)0.2278 (2)0.1784 (2)0.0453 (6)
C9A0.0536 (2)0.2783 (2)0.5026 (2)0.0386 (5)
C9B0.1927 (2)0.1623 (2)0.2467 (2)0.0442 (6)
C10A−0.0308 (2)0.1731 (2)0.5044 (2)0.0411 (6)
H10A−0.00320.13710.55390.049*
C10B0.1087 (2)0.0598 (2)0.2493 (2)0.0451 (6)
H10B0.13730.02030.29510.054*
C11A−0.1580 (2)0.1204 (2)0.4318 (2)0.0385 (5)
C11B−0.0197 (2)0.0135 (2)0.1839 (2)0.0437 (6)
C12A−0.2003 (2)0.1743 (2)0.3635 (2)0.0389 (5)
H12A−0.28830.13840.31640.047*
C12B−0.0629 (2)0.0708 (2)0.1180 (2)0.0397 (6)
H12B−0.15170.03840.07420.048*
C13A−0.1151 (2)0.2806 (2)0.36324 (19)0.0376 (5)
C13B0.0225 (2)0.1740 (2)0.1161 (2)0.0379 (5)
N14A0.18554 (19)0.33227 (19)0.58082 (19)0.0484 (5)
N14B0.3273 (2)0.2071 (2)0.3173 (2)0.0579 (6)
N15A−0.2477 (2)0.00586 (19)0.4296 (2)0.0524 (6)
N15B−0.1106 (2)−0.0986 (2)0.1844 (2)0.0608 (6)
N16A−0.1678 (2)0.3358 (2)0.29156 (18)0.0493 (5)
N16B−0.0302 (2)0.2282 (2)0.04259 (18)0.0481 (5)
U11U22U33U12U13U23
O1A0.0453 (9)0.0539 (10)0.0624 (12)0.0011 (8)0.0076 (8)0.0413 (9)
O1B0.0462 (11)0.1026 (15)0.1073 (17)−0.0049 (10)0.0033 (10)0.0862 (14)
O2A0.0380 (10)0.1079 (16)0.0862 (15)0.0112 (10)0.0115 (10)0.0646 (13)
O2B0.0465 (11)0.0889 (15)0.1088 (18)0.0002 (9)−0.0047 (11)0.0659 (14)
O3A0.0661 (12)0.0843 (14)0.0561 (13)0.0079 (10)−0.0046 (10)0.0474 (11)
O3B0.0629 (13)0.1237 (19)0.133 (2)0.0345 (12)0.0134 (13)0.1004 (17)
O4A0.0800 (14)0.0627 (12)0.0970 (16)0.0110 (10)0.0246 (12)0.0615 (12)
O4B0.1063 (18)0.0910 (16)0.115 (2)0.0131 (13)0.0293 (15)0.0845 (16)
O5A0.0518 (12)0.0658 (13)0.0883 (16)−0.0106 (9)0.0091 (11)0.0419 (11)
O5B0.0642 (14)0.0994 (17)0.125 (2)−0.0206 (12)0.0024 (14)0.0711 (16)
O6A0.0481 (13)0.155 (2)0.149 (2)0.0152 (13)−0.0001 (13)0.125 (2)
O6B0.0508 (12)0.1075 (17)0.1051 (18)0.0075 (11)−0.0084 (11)0.0770 (15)
O7A0.0610 (12)0.0790 (14)0.0779 (14)0.0147 (10)0.0102 (10)0.0622 (12)
O7B0.0596 (12)0.1074 (17)0.1231 (19)0.0117 (11)0.0115 (12)0.0975 (16)
N1A0.0437 (12)0.0441 (12)0.0469 (13)0.0100 (10)0.0118 (10)0.0295 (10)
N1B0.0379 (11)0.0573 (13)0.0522 (13)0.0089 (10)0.0078 (10)0.0366 (11)
C2A0.0578 (16)0.0597 (16)0.0533 (17)0.0205 (13)0.0128 (13)0.0374 (14)
C2B0.0525 (16)0.078 (2)0.0618 (19)0.0157 (14)0.0065 (14)0.0446 (16)
C3A0.082 (2)0.077 (2)0.0677 (19)0.0430 (17)0.0314 (17)0.0548 (17)
C3B0.074 (2)0.083 (2)0.077 (2)0.0290 (17)0.0280 (17)0.0624 (19)
C4A0.073 (2)0.0548 (17)0.081 (2)0.0231 (15)0.0380 (17)0.0486 (16)
C4B0.0669 (19)0.0553 (17)0.076 (2)0.0164 (14)0.0293 (16)0.0416 (16)
C5A0.0527 (16)0.0488 (16)0.0662 (19)0.0100 (12)0.0244 (14)0.0306 (14)
C5B0.0447 (14)0.0481 (15)0.0608 (18)0.0077 (11)0.0136 (13)0.0279 (13)
C6A0.0453 (14)0.0408 (14)0.0435 (14)0.0143 (11)0.0183 (12)0.0230 (11)
C6B0.0379 (13)0.0460 (14)0.0438 (15)0.0119 (11)0.0133 (11)0.0231 (12)
N7A0.0419 (13)0.0706 (16)0.0612 (16)0.0119 (12)0.0070 (11)0.0453 (13)
N7B0.0372 (14)0.0818 (19)0.0681 (18)0.0050 (13)0.0020 (13)0.0498 (15)
C8A0.0390 (12)0.0337 (13)0.0361 (13)0.0073 (10)0.0102 (10)0.0210 (10)
C8B0.0393 (13)0.0530 (15)0.0489 (15)0.0108 (11)0.0113 (11)0.0332 (13)
C9A0.0371 (12)0.0378 (13)0.0385 (13)0.0090 (10)0.0062 (10)0.0206 (11)
C9B0.0371 (13)0.0518 (15)0.0475 (15)0.0125 (11)0.0105 (11)0.0301 (12)
C10A0.0508 (14)0.0338 (13)0.0418 (14)0.0122 (10)0.0128 (11)0.0232 (11)
C10B0.0503 (14)0.0494 (15)0.0479 (15)0.0201 (12)0.0178 (12)0.0321 (12)
C11A0.0411 (13)0.0319 (12)0.0413 (14)0.0061 (10)0.0139 (11)0.0198 (11)
C11B0.0489 (14)0.0394 (14)0.0460 (15)0.0121 (11)0.0229 (12)0.0221 (12)
C12A0.0339 (12)0.0365 (13)0.0371 (13)0.0058 (9)0.0050 (10)0.0155 (11)
C12B0.0375 (12)0.0401 (13)0.0387 (13)0.0111 (10)0.0123 (10)0.0177 (11)
C13A0.0404 (13)0.0379 (13)0.0327 (13)0.0104 (10)0.0067 (10)0.0191 (11)
C13B0.0408 (13)0.0402 (13)0.0374 (13)0.0136 (10)0.0133 (10)0.0229 (11)
N14A0.0434 (12)0.0460 (12)0.0535 (14)0.0072 (9)0.0024 (10)0.0315 (11)
N14B0.0453 (12)0.0751 (14)0.0697 (16)0.0203 (9)0.0157 (11)0.0506 (13)
N15A0.0556 (14)0.0400 (12)0.0576 (14)0.0050 (10)0.0217 (11)0.0249 (11)
N15B0.0629 (15)0.0514 (14)0.0633 (16)0.0033 (11)0.0245 (13)0.0306 (12)
N16A0.0453 (12)0.0518 (13)0.0482 (13)0.0064 (10)0.0013 (10)0.0328 (11)
N16B0.0438 (12)0.0560 (13)0.0491 (13)0.0166 (10)0.0112 (10)0.0311 (11)
O1A—C8A1.252 (2)C5A—C6A1.416 (3)
O1B—C8B1.237 (3)C5A—H5A0.9500
O2A—N14A1.214 (3)C5B—C6B1.393 (3)
O2B—N14B1.208 (3)C5B—H5B0.9500
O3A—N14A1.217 (2)C6A—N7A1.331 (3)
O3B—N14B1.226 (2)C6B—N7B1.312 (3)
O4A—N15A1.230 (3)N7A—H7A0.87 (3)
O4B—N15B1.212 (3)N7A—H7B1.05 (3)
O5A—N15A1.214 (3)N7B—H7C0.72 (3)
O5B—N15B1.212 (3)N7B—H7D0.84 (3)
O6A—N16A1.209 (2)C8A—C13A1.436 (3)
O6B—N16B1.206 (2)C8A—C9A1.446 (3)
O7A—N16A1.208 (2)C8B—C13B1.441 (3)
O7B—N16B1.197 (2)C8B—C9B1.450 (3)
N1A—C6A1.339 (3)C9A—C10A1.371 (3)
N1A—C2A1.350 (3)C9A—N14A1.454 (3)
N1A—H1A0.87 (3)C9B—C10B1.351 (3)
N1B—C6B1.352 (3)C9B—N14B1.461 (3)
N1B—C2B1.356 (3)C10A—C11A1.389 (3)
N1B—H1B0.96 (3)C10A—H10A0.9500
C2A—C3A1.348 (3)C10B—C11B1.381 (3)
C2A—H2A0.9500C10B—H10B0.9500
C2B—C3B1.347 (4)C11A—C12A1.367 (3)
C2B—H2B0.9500C11A—N15A1.453 (3)
C3A—C4A1.391 (4)C11B—C12B1.379 (3)
C3A—H3A0.9500C11B—N15B1.457 (3)
C3B—C4B1.390 (4)C12A—C13A1.374 (3)
C3B—H3B0.9500C12A—H12A0.9500
C4A—C5A1.348 (3)C12B—C13B1.359 (3)
C4A—H4A0.9500C12B—H12B0.9500
C4B—C5B1.351 (4)C13A—N16A1.456 (3)
C4B—H4B0.9500C13B—N16B1.465 (3)
C6A—N1A—C2A123.2 (2)C10A—C9A—C8A124.6 (2)
C6A—N1A—H1A121.2 (17)C10A—C9A—N14A116.76 (19)
C2A—N1A—H1A115.6 (17)C8A—C9A—N14A118.66 (19)
C6B—N1B—C2B122.5 (2)C10B—C9B—C8B124.8 (2)
C6B—N1B—H1B115.8 (15)C10B—C9B—N14B116.4 (2)
C2B—N1B—H1B121.7 (15)C8B—C9B—N14B118.8 (2)
C3A—C2A—N1A120.1 (3)C9A—C10A—C11A118.2 (2)
C3A—C2A—H2A120.0C9A—C10A—H10A120.9
N1A—C2A—H2A120.0C11A—C10A—H10A120.9
C3B—C2B—N1B120.8 (3)C9B—C10B—C11B118.6 (2)
C3B—C2B—H2B119.6C9B—C10B—H10B120.7
N1B—C2B—H2B119.6C11B—C10B—H10B120.7
C2A—C3A—C4A118.9 (2)C12A—C11A—C10A121.5 (2)
C2A—C3A—H3A120.6C12A—C11A—N15A119.6 (2)
C4A—C3A—H3A120.6C10A—C11A—N15A118.9 (2)
C2B—C3B—C4B117.8 (3)C12B—C11B—C10B121.4 (2)
C2B—C3B—H3B121.1C12B—C11B—N15B119.6 (2)
C4B—C3B—H3B121.1C10B—C11B—N15B119.0 (2)
C5A—C4A—C3A120.8 (2)C11A—C12A—C13A119.8 (2)
C5A—C4A—H4A119.6C11A—C12A—H12A120.1
C3A—C4A—H4A119.6C13A—C12A—H12A120.1
C5B—C4B—C3B121.7 (2)C13B—C12B—C11B119.5 (2)
C5B—C4B—H4B119.2C13B—C12B—H12B120.3
C3B—C4B—H4B119.2C11B—C12B—H12B120.3
C4A—C5A—C6A119.6 (3)C12A—C13A—C8A123.6 (2)
C4A—C5A—H5A120.2C12A—C13A—N16A116.78 (19)
C6A—C5A—H5A120.2C8A—C13A—N16A119.61 (19)
C4B—C5B—C6B119.7 (2)C12B—C13B—C8B123.8 (2)
C4B—C5B—H5B120.2C12B—C13B—N16B116.4 (2)
C6B—C5B—H5B120.2C8B—C13B—N16B119.77 (19)
N7A—C6A—N1A118.9 (2)O2A—N14A—O3A122.7 (2)
N7A—C6A—C5A123.7 (2)O2A—N14A—C9A119.2 (2)
N1A—C6A—C5A117.4 (2)O3A—N14A—C9A118.1 (2)
N7B—C6B—N1B118.1 (2)O2B—N14B—O3B121.8 (2)
N7B—C6B—C5B124.3 (2)O2B—N14B—C9B120.4 (2)
N1B—C6B—C5B117.6 (2)O3B—N14B—C9B117.7 (2)
C6A—N7A—H7A118 (2)O5A—N15A—O4A123.5 (2)
C6A—N7A—H7B120.8 (17)O5A—N15A—C11A118.3 (2)
H7A—N7A—H7B120 (3)O4A—N15A—C11A118.2 (2)
C6B—N7B—H7C114 (2)O4B—N15B—O5B123.4 (2)
C6B—N7B—H7D117.1 (19)O4B—N15B—C11B118.7 (2)
H7C—N7B—H7D129 (3)O5B—N15B—C11B117.9 (2)
O1A—C8A—C13A125.4 (2)O7A—N16A—O6A121.4 (2)
O1A—C8A—C9A122.2 (2)O7A—N16A—C13A120.0 (2)
C13A—C8A—C9A112.30 (19)O6A—N16A—C13A118.5 (2)
O1B—C8B—C13B124.9 (2)O7B—N16B—O6B121.4 (2)
O1B—C8B—C9B123.2 (2)O7B—N16B—C13B120.5 (2)
C13B—C8B—C9B111.9 (2)O6B—N16B—C13B118.1 (2)
D—H···AD—HH···AD···AD—H···A
N1B—H1B···O1B0.96 (3)1.79 (3)2.681 (3)152 (2)
N1B—H1B···O7B0.96 (3)2.36 (3)3.035 (3)127 (2)
N7B—H7D···O1B0.84 (3)2.04 (3)2.784 (3)148 (3)
N7B—H7D···O2B0.84 (3)2.47 (3)3.165 (3)141 (2)
N1A—H1A···O1A0.87 (3)1.97 (3)2.726 (2)145 (2)
N1A—H1A···O7A0.87 (3)2.34 (3)3.031 (3)137 (2)
N7A—H7B···O2A1.05 (3)2.40 (3)3.329 (3)147 (2)
C10A—H10A···O4Bi0.952.573.438 (3)153
N7A—H7A···O2Bii0.87 (3)2.24 (3)3.029 (3)152 (3)
N7B—H7C···O2Aii0.72 (3)2.49 (3)3.137 (3)149 (3)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1B—H1B⋯O1B0.96 (3)1.79 (3)2.681 (3)152 (2)
N1B—H1B⋯O7B0.96 (3)2.36 (3)3.035 (3)127 (2)
N7B—H7D⋯O1B0.84 (3)2.04 (3)2.784 (3)148 (3)
N7B—H7D⋯O2B0.84 (3)2.47 (3)3.165 (3)141 (2)
N1A—H1A⋯O1A0.87 (3)1.97 (3)2.726 (2)145 (2)
N1A—H1A⋯O7A0.87 (3)2.34 (3)3.031 (3)137 (2)
N7A—H7B⋯O2A1.05 (3)2.40 (3)3.329 (3)147 (2)
C10A—H10A⋯O4Bi0.952.573.438 (3)153
N7A—H7A⋯O2Bii0.87 (3)2.24 (3)3.029 (3)152 (3)
N7B—H7C⋯O2Aii0.72 (3)2.49 (3)3.137 (3)149 (3)

Symmetry codes: (i) ; (ii) .

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