Literature DB >> 22259478

Acridin-10-ium 6-carb-oxy-pyridine-2-carboxyl-ate.

Kwang Ha1.   

Abstract

The title compound, C(13)H(10)N(+)·C(7)H(4)NO(4) (-), consists of a protonated acridinium cation and a 6-carb-oxy-pyridine-2-carboxyl-ate monoanion. The carboxyl-ate group of the anion appears to be delocalized on the basis of the nearly equivalent C-O bond lengths. In the crystal, the anions are connected by strong O-H⋯O hydrogen bonds, forming chains along the b axis. The acridinium cations are linked to the anionic chains by strong N-H⋯O hydrogen bonds between the carboxyl-ate group of the anion and the N-H group of the cation. Along the b axis, successive chains stack in opposite directions. Weak inter-molecular C-H⋯O hydrogen bonds further stabilize the crystal structure.

Entities:  

Year:  2011        PMID： 22259478      PMCID： PMC3254532          DOI： 10.1107/S1600536811053578

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


Related literature

For related crystal structures of acridinium compounds with carboxyl­ate, see: Shaameri et al. (2001 ▶); Derikvand et al. (2009 ▶); Attar Gharamaleki et al. (2010 ▶).

Experimental

Crystal data

C13H10N+·C7H4NO4 − M = 346.33 Monoclinic, a = 16.6817 (8) Å b = 8.2872 (4) Å c = 23.7289 (12) Å β = 105.582 (1)° V = 3159.8 (3) Å3 Z = 8 Mo Kα radiation μ = 0.10 mm−1 T = 200 K 0.29 × 0.18 × 0.17 mm

Data collection

Bruker SMART 1000 CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.884, T max = 1.000 11354 measured reflections 3894 independent reflections 2198 reflections with I > 2σ(I) R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.140 S = 1.06 3894 reflections 235 parameters H-atom parameters constrained Δρmax = 0.31 e Å−3 Δρmin = −0.27 e Å−3 Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053578/su2350sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053578/su2350Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811053578/su2350Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H10N+·C7H4NO4−F(000) = 1440
Mr = 346.33Dx = 1.456 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3018 reflections
a = 16.6817 (8) Åθ = 2.5–27.8°
b = 8.2872 (4) ŵ = 0.10 mm−1
c = 23.7289 (12) ÅT = 200 K
β = 105.582 (1)°Block, yellow
V = 3159.8 (3) Å30.29 × 0.18 × 0.17 mm
Z = 8
Bruker SMART 1000 CCD diffractometer3894 independent reflections
Radiation source: fine-focus sealed tube2198 reflections with I > 2σ(I)
graphiteRint = 0.046
φ and ω scansθmax = 28.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −22→19
Tmin = 0.884, Tmax = 1.000k = −10→11
11354 measured reflectionsl = −29→31
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0484P)2 + 0.8669P] where P = (Fo2 + 2Fc2)/3
3894 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.27 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
N1−0.04881 (10)0.2361 (2)−0.00985 (7)0.0305 (4)
H1N−0.10010.2338−0.03670.046*
C1−0.04063 (12)0.1529 (2)0.04054 (9)0.0300 (5)
C2−0.11101 (13)0.0861 (3)0.05417 (10)0.0369 (5)
H2−0.16480.09860.02800.044*
C3−0.10107 (14)0.0039 (3)0.10497 (10)0.0410 (6)
H3−0.1486−0.03970.11430.049*
C4−0.02137 (14)−0.0185 (3)0.14456 (10)0.0408 (6)
H4−0.0161−0.07660.17990.049*
C50.04717 (14)0.0427 (3)0.13213 (9)0.0366 (5)
H50.10050.02580.15840.044*
C60.03965 (13)0.1322 (3)0.07986 (9)0.0308 (5)
C70.10755 (13)0.2029 (3)0.06581 (9)0.0338 (5)
H70.16170.18840.09120.041*
C80.09735 (12)0.2943 (3)0.01523 (9)0.0317 (5)
C90.16393 (14)0.3735 (3)−0.00016 (10)0.0413 (6)
H90.21830.36900.02570.050*
C100.15110 (15)0.4556 (3)−0.05128 (11)0.0446 (6)
H100.19650.5060−0.06130.054*
C110.07003 (14)0.4662 (3)−0.08980 (10)0.0408 (6)
H110.06180.5243−0.12540.049*
C120.00364 (14)0.3949 (3)−0.07683 (9)0.0344 (5)
H12−0.05040.4037−0.10290.041*
C130.01634 (12)0.3078 (2)−0.02393 (9)0.0294 (5)
O10.24957 (9)0.82325 (18)0.32785 (7)0.0433 (4)
H1O0.25330.92410.33110.065*
O20.13288 (10)0.87006 (19)0.25747 (7)0.0475 (5)
O30.30738 (9)0.32253 (19)0.41697 (7)0.0431 (4)
O40.29134 (9)0.11156 (19)0.35743 (7)0.0462 (5)
N20.22360 (10)0.5100 (2)0.32603 (7)0.0295 (4)
C140.17072 (12)0.5985 (3)0.28554 (9)0.0295 (5)
C150.10598 (13)0.5332 (3)0.24202 (10)0.0369 (5)
H150.06860.60070.21480.044*
C160.09746 (14)0.3678 (3)0.23931 (10)0.0407 (6)
H160.05400.31920.20990.049*
C170.15273 (13)0.2735 (3)0.27968 (9)0.0346 (5)
H170.14890.15910.27790.041*
C180.21413 (12)0.3490 (2)0.32294 (9)0.0284 (5)
C190.18181 (13)0.7786 (3)0.28826 (9)0.0315 (5)
C200.27569 (12)0.2525 (3)0.36928 (10)0.0317 (5)
U11U22U33U12U13U23
N10.0284 (9)0.0307 (10)0.0287 (10)−0.0019 (8)0.0014 (8)−0.0006 (8)
C10.0333 (11)0.0281 (12)0.0270 (11)0.0005 (9)0.0054 (9)−0.0018 (9)
C20.0321 (12)0.0428 (14)0.0339 (13)−0.0032 (10)0.0056 (10)0.0001 (11)
C30.0422 (13)0.0437 (15)0.0396 (14)−0.0047 (11)0.0153 (11)0.0029 (11)
C40.0491 (14)0.0400 (14)0.0331 (13)0.0023 (11)0.0106 (11)0.0059 (10)
C50.0410 (13)0.0360 (13)0.0290 (12)0.0066 (10)0.0030 (10)0.0012 (10)
C60.0328 (11)0.0285 (12)0.0289 (12)0.0023 (9)0.0048 (9)−0.0046 (9)
C70.0286 (11)0.0379 (13)0.0300 (12)0.0006 (10)−0.0005 (9)−0.0045 (10)
C80.0315 (11)0.0307 (12)0.0313 (12)−0.0033 (9)0.0055 (9)−0.0052 (10)
C90.0309 (12)0.0485 (15)0.0416 (14)−0.0053 (11)0.0045 (10)−0.0037 (12)
C100.0423 (14)0.0479 (16)0.0468 (15)−0.0110 (12)0.0173 (11)−0.0029 (12)
C110.0490 (14)0.0371 (14)0.0369 (14)−0.0043 (11)0.0124 (11)0.0029 (11)
C120.0377 (12)0.0328 (13)0.0303 (12)−0.0004 (10)0.0047 (10)−0.0012 (10)
C130.0294 (11)0.0262 (12)0.0319 (12)−0.0030 (9)0.0072 (9)−0.0048 (9)
O10.0412 (9)0.0265 (9)0.0531 (11)0.0000 (7)−0.0029 (8)0.0003 (7)
O20.0533 (10)0.0325 (9)0.0460 (10)0.0081 (8)−0.0049 (8)0.0074 (8)
O30.0454 (9)0.0406 (10)0.0344 (9)0.0111 (8)−0.0047 (7)−0.0041 (8)
O40.0396 (9)0.0277 (9)0.0617 (12)0.0043 (7)−0.0029 (8)−0.0070 (8)
N20.0277 (9)0.0319 (10)0.0283 (10)0.0035 (8)0.0063 (7)0.0020 (8)
C140.0302 (11)0.0292 (12)0.0292 (12)0.0011 (9)0.0082 (9)0.0007 (9)
C150.0375 (12)0.0381 (14)0.0305 (12)0.0037 (10)0.0010 (10)0.0012 (10)
C160.0375 (12)0.0389 (14)0.0375 (14)−0.0019 (11)−0.0040 (10)−0.0047 (11)
C170.0349 (12)0.0292 (12)0.0354 (13)−0.0003 (10)0.0021 (10)−0.0034 (10)
C180.0276 (10)0.0262 (12)0.0313 (12)0.0005 (9)0.0077 (9)−0.0008 (9)
C190.0330 (11)0.0324 (12)0.0285 (12)0.0009 (10)0.0071 (9)0.0023 (10)
C200.0270 (11)0.0295 (13)0.0371 (13)0.0002 (9)0.0057 (10)−0.0005 (10)
N1—C11.355 (3)C10—H100.9500
N1—C131.357 (3)C11—C121.361 (3)
N1—H1N0.9200C11—H110.9500
C1—C21.412 (3)C12—C131.414 (3)
C1—C61.422 (3)C12—H120.9500
C2—C31.355 (3)O1—C191.314 (2)
C2—H20.9500O1—H1O0.8400
C3—C41.419 (3)O2—C191.206 (2)
C3—H30.9500O3—C201.255 (2)
C4—C51.354 (3)O4—C201.246 (3)
C4—H40.9500N2—C141.335 (3)
C5—C61.421 (3)N2—C181.344 (3)
C5—H50.9500C14—C151.388 (3)
C6—C71.393 (3)C14—C191.503 (3)
C7—C81.390 (3)C15—C161.378 (3)
C7—H70.9500C15—H150.9500
C8—C91.420 (3)C16—C171.380 (3)
C8—C131.424 (3)C16—H160.9500
C9—C101.357 (3)C17—C181.389 (3)
C9—H90.9500C17—H170.9500
C10—C111.417 (3)C18—C201.515 (3)
C1—N1—C13122.86 (17)C12—C11—C10121.4 (2)
C1—N1—H1N117.1C12—C11—H11119.3
C13—N1—H1N119.7C10—C11—H11119.3
N1—C1—C2120.59 (18)C11—C12—C13119.0 (2)
N1—C1—C6119.62 (19)C11—C12—H12120.5
C2—C1—C6119.8 (2)C13—C12—H12120.5
C3—C2—C1119.3 (2)N1—C13—C12120.22 (18)
C3—C2—H2120.3N1—C13—C8119.18 (19)
C1—C2—H2120.3C12—C13—C8120.60 (19)
C2—C3—C4121.6 (2)C19—O1—H1O112.0
C2—C3—H3119.2C14—N2—C18117.44 (18)
C4—C3—H3119.2N2—C14—C15123.6 (2)
C5—C4—C3120.2 (2)N2—C14—C19117.66 (19)
C5—C4—H4119.9C15—C14—C19118.77 (19)
C3—C4—H4119.9C16—C15—C14118.2 (2)
C4—C5—C6120.3 (2)C16—C15—H15120.9
C4—C5—H5119.9C14—C15—H15120.9
C6—C5—H5119.9C15—C16—C17119.3 (2)
C7—C6—C5122.78 (19)C15—C16—H16120.3
C7—C6—C1118.4 (2)C17—C16—H16120.3
C5—C6—C1118.8 (2)C16—C17—C18118.7 (2)
C8—C7—C6121.12 (19)C16—C17—H17120.6
C8—C7—H7119.4C18—C17—H17120.6
C6—C7—H7119.4N2—C18—C17122.70 (19)
C7—C8—C9123.4 (2)N2—C18—C20115.95 (18)
C7—C8—C13118.73 (19)C17—C18—C20121.34 (19)
C9—C8—C13117.8 (2)O2—C19—O1124.6 (2)
C10—C9—C8121.0 (2)O2—C19—C14122.9 (2)
C10—C9—H9119.5O1—C19—C14112.50 (18)
C8—C9—H9119.5O4—C20—O3125.0 (2)
C9—C10—C11120.1 (2)O4—C20—C18118.25 (19)
C9—C10—H10119.9O3—C20—C18116.73 (19)
C11—C10—H10119.9
C13—N1—C1—C2177.4 (2)C11—C12—C13—N1179.8 (2)
C13—N1—C1—C6−2.9 (3)C11—C12—C13—C8−0.1 (3)
N1—C1—C2—C3−179.8 (2)C7—C8—C13—N12.3 (3)
C6—C1—C2—C30.5 (3)C9—C8—C13—N1−178.68 (19)
C1—C2—C3—C4−0.8 (4)C7—C8—C13—C12−177.8 (2)
C2—C3—C4—C50.0 (4)C9—C8—C13—C121.2 (3)
C3—C4—C5—C61.1 (4)C18—N2—C14—C151.8 (3)
C4—C5—C6—C7177.6 (2)C18—N2—C14—C19−179.12 (18)
C4—C5—C6—C1−1.4 (3)N2—C14—C15—C16−2.2 (3)
N1—C1—C6—C71.8 (3)C19—C14—C15—C16178.8 (2)
C2—C1—C6—C7−178.5 (2)C14—C15—C16—C170.3 (4)
N1—C1—C6—C5−179.16 (19)C15—C16—C17—C181.7 (3)
C2—C1—C6—C50.6 (3)C14—N2—C18—C170.4 (3)
C5—C6—C7—C8−177.7 (2)C14—N2—C18—C20179.50 (18)
C1—C6—C7—C81.2 (3)C16—C17—C18—N2−2.2 (3)
C6—C7—C8—C9177.8 (2)C16—C17—C18—C20178.8 (2)
C6—C7—C8—C13−3.2 (3)N2—C14—C19—O2−172.6 (2)
C7—C8—C9—C10177.2 (2)C15—C14—C19—O26.5 (3)
C13—C8—C9—C10−1.8 (3)N2—C14—C19—O16.8 (3)
C8—C9—C10—C111.3 (4)C15—C14—C19—O1−174.07 (19)
C9—C10—C11—C12−0.2 (4)N2—C18—C20—O4−153.4 (2)
C10—C11—C12—C13−0.4 (3)C17—C18—C20—O425.7 (3)
C1—N1—C13—C12−179.1 (2)N2—C18—C20—O326.3 (3)
C1—N1—C13—C80.8 (3)C17—C18—C20—O3−154.6 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1N···O3i0.921.702.602 (2)165.
O1—H1O···O4ii0.841.732.535 (2)160.
C7—H7···O1iii0.952.373.132 (2)137.
C10—H10···O3iv0.952.493.435 (3)171.
C12—H12···O4i0.952.563.466 (3)160.
C17—H17···O2v0.952.443.387 (3)171.
O1—C191.314 (2)
O2—C191.206 (2)
O3—C201.255 (2)
O4—C201.246 (3)
O2—C19—O1124.6 (2)
O4—C20—O3125.0 (2)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1N⋯O3i0.921.702.602 (2)165
O1—H1O⋯O4ii0.841.732.535 (2)160
C7—H7⋯O1iii0.952.373.132 (2)137
C10—H10⋯O3iv0.952.493.435 (3)171
C12—H12⋯O4i0.952.563.466 (3)160
C17—H17⋯O2v0.952.443.387 (3)171

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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