Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013927/ya6049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013927/ya6049Isup2.hkl |
CCDC reference: 175361
Acridine and isophthalic acid were obtained from Aldrich. 33 mg of the acid and 36 mg of the base were used to dissolve into 15 ml of ethanol. Crystals of (I) were obtained by slow evaporation of the ethanol solution at the room temperature.
The H101 atom on the carboxylic acid group was located from the difference Fourier map and refined without restraint. All other H atoms were placed geometrically and allowed to ride on their parent atom during subsequent refinement, with an isotropic displacement parameter fixed at 1.2 times the Ueq value of the corresponding C or N atom.
Data collection: CAD-4 Software (Enraf-Nonius, 1988); cell refinement: CAD-4 Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993); software used to prepare material for publication: SHELXL97.
C13H10N+·C8H5O4− | Z = 2 |
Mr = 345.34 | F(000) = 360 |
Triclinic, P1 | Dx = 1.389 Mg m−3 |
a = 8.5196 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.144 (1) Å | Cell parameters from 25 reflections |
c = 11.386 (4) Å | θ = 8.0–15.0° |
α = 69.41 (2)° | µ = 0.10 mm−1 |
β = 89.44 (1)° | T = 295 K |
γ = 84.22 (1)° | Block, yellow |
V = 825.8 (3) Å3 | 0.50 × 0.25 × 0.15 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.023 |
Radiation source: fine-focus sealed tube | θmax = 24.9°, θmin = 3.5° |
Graphite monochromator | h = −10→10 |
ω/2θ scans | k = −10→10 |
3032 measured reflections | l = 0→13 |
2874 independent reflections | 3 standard reflections every 200 reflections |
2054 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0389P)2 + 0.2511P] where P = (Fo2 + 2Fc2)/3 |
2874 reflections | (Δ/σ)max < 0.001 |
239 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C13H10N+·C8H5O4− | γ = 84.22 (1)° |
Mr = 345.34 | V = 825.8 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5196 (9) Å | Mo Kα radiation |
b = 9.144 (1) Å | µ = 0.10 mm−1 |
c = 11.386 (4) Å | T = 295 K |
α = 69.41 (2)° | 0.50 × 0.25 × 0.15 mm |
β = 89.44 (1)° |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.023 |
3032 measured reflections | 3 standard reflections every 200 reflections |
2874 independent reflections | intensity decay: none |
2054 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.16 e Å−3 |
2874 reflections | Δρmin = −0.27 e Å−3 |
239 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 | ||
C1 | 0.1914 (2) | 0.5425 (2) | 0.05355 (18) | 0.0397 (5) | |
C2 | 0.0934 (3) | 0.5486 (3) | 0.1533 (2) | 0.0524 (6) | |
H2 | 0.0545 | 0.4578 | 0.2067 | 0.063* | |
C3 | 0.0565 (3) | 0.6866 (3) | 0.1706 (3) | 0.0683 (7) | |
H3 | −0.0065 | 0.6896 | 0.2371 | 0.082* | |
C4 | 0.1114 (4) | 0.8249 (3) | 0.0903 (3) | 0.0736 (8) | |
H4 | 0.0851 | 0.9185 | 0.1043 | 0.088* | |
C5 | 0.2023 (3) | 0.8243 (3) | −0.0074 (3) | 0.0675 (7) | |
H5 | 0.2366 | 0.9176 | −0.0608 | 0.081* | |
C6 | 0.2458 (2) | 0.6823 (2) | −0.02912 (19) | 0.0466 (5) | |
C7 | 0.3398 (3) | 0.6711 (3) | −0.1264 (2) | 0.0544 (6) | |
H7 | 0.3776 | 0.7612 | −0.1820 | 0.065* | |
C8 | 0.3784 (2) | 0.5298 (3) | −0.14236 (19) | 0.0476 (5) | |
C9 | 0.4724 (3) | 0.5118 (4) | −0.2416 (2) | 0.0694 (7) | |
H9 | 0.5110 | 0.5992 | −0.3001 | 0.083* | |
C10 | 0.5058 (3) | 0.3697 (5) | −0.2515 (3) | 0.0838 (10) | |
H10 | 0.5667 | 0.3598 | −0.3171 | 0.101* | |
C11 | 0.4492 (3) | 0.2358 (4) | −0.1633 (3) | 0.0792 (9) | |
H11 | 0.4737 | 0.1385 | −0.1715 | 0.095* | |
C12 | 0.3600 (3) | 0.2459 (3) | −0.0673 (2) | 0.0604 (6) | |
H12 | 0.3239 | 0.1564 | −0.0095 | 0.072* | |
C13 | 0.3222 (2) | 0.3933 (2) | −0.05556 (19) | 0.0419 (5) | |
C14 | 0.1152 (2) | 0.9353 (2) | 0.36771 (18) | 0.0371 (4) | |
C15 | −0.0485 (2) | 0.9496 (2) | 0.36344 (18) | 0.0387 (5) | |
H15 | −0.1037 | 1.0405 | 0.3084 | 0.046* | |
C16 | −0.1309 (2) | 0.8297 (2) | 0.44059 (18) | 0.0393 (5) | |
C17 | −0.0475 (3) | 0.6944 (2) | 0.52102 (19) | 0.0492 (5) | |
H17 | −0.1012 | 0.6123 | 0.5715 | 0.059* | |
C18 | 0.1157 (3) | 0.6809 (3) | 0.5266 (2) | 0.0548 (6) | |
H18 | 0.1711 | 0.5899 | 0.5812 | 0.066* | |
C19 | 0.1963 (2) | 0.8011 (2) | 0.4518 (2) | 0.0487 (5) | |
H19 | 0.3059 | 0.7922 | 0.4578 | 0.058* | |
C20 | 0.2007 (2) | 1.0627 (2) | 0.2786 (2) | 0.0430 (5) | |
O1 | 0.11318 (16) | 1.16990 (17) | 0.19597 (15) | 0.0576 (5) | |
O2 | 0.34385 (17) | 1.0593 (2) | 0.28384 (17) | 0.0726 (5) | |
O3 | −0.36907 (18) | 0.98302 (19) | 0.36458 (17) | 0.0673 (5) | |
H101 | −0.493 (4) | 0.986 (3) | 0.363 (3) | 0.102 (9)* | |
O4 | −0.38280 (19) | 0.7372 (2) | 0.49132 (16) | 0.0697 (5) | |
C21 | −0.3057 (2) | 0.8430 (3) | 0.43635 (19) | 0.0460 (5) | |
N1 | 0.23126 (18) | 0.40482 (19) | 0.03912 (15) | 0.0408 (4) | |
H1 | 0.1980 | 0.3213 | 0.0916 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C14 | 0.0353 (10) | 0.0420 (11) | 0.0359 (10) | −0.0065 (8) | 0.0056 (8) | −0.0155 (9) |
O3 | 0.0354 (9) | 0.0595 (10) | 0.0841 (13) | −0.0094 (7) | 0.0016 (8) | 0.0044 (9) |
O1 | 0.0406 (8) | 0.0522 (9) | 0.0624 (10) | −0.0115 (7) | 0.0028 (7) | 0.0035 (8) |
C16 | 0.0400 (10) | 0.0440 (11) | 0.0346 (10) | −0.0090 (8) | 0.0044 (8) | −0.0133 (9) |
C20 | 0.0368 (11) | 0.0458 (12) | 0.0462 (12) | −0.0089 (9) | 0.0045 (9) | −0.0150 (10) |
C17 | 0.0526 (13) | 0.0466 (12) | 0.0408 (12) | −0.0136 (10) | 0.0058 (10) | −0.0040 (10) |
O4 | 0.0526 (10) | 0.0711 (11) | 0.0677 (11) | −0.0270 (8) | 0.0117 (8) | 0.0027 (9) |
C15 | 0.0384 (11) | 0.0386 (11) | 0.0377 (11) | −0.0052 (8) | 0.0016 (8) | −0.0112 (9) |
O2 | 0.0326 (9) | 0.0817 (12) | 0.0804 (12) | −0.0141 (8) | 0.0030 (8) | 0.0024 (10) |
C19 | 0.0393 (11) | 0.0524 (13) | 0.0506 (13) | −0.0007 (9) | −0.0002 (10) | −0.0145 (10) |
C21 | 0.0442 (11) | 0.0532 (13) | 0.0367 (11) | −0.0141 (10) | 0.0078 (9) | −0.0087 (10) |
C18 | 0.0517 (13) | 0.0463 (13) | 0.0528 (13) | −0.0012 (10) | −0.0043 (11) | −0.0013 (10) |
N1 | 0.0403 (9) | 0.0406 (9) | 0.0386 (9) | −0.0108 (7) | 0.0080 (7) | −0.0088 (7) |
C1 | 0.0393 (10) | 0.0415 (12) | 0.0372 (11) | −0.0033 (9) | −0.0014 (8) | −0.0125 (9) |
C13 | 0.0340 (10) | 0.0536 (13) | 0.0421 (11) | −0.0073 (9) | 0.0041 (9) | −0.0212 (10) |
C6 | 0.0516 (12) | 0.0421 (12) | 0.0414 (12) | −0.0037 (9) | −0.0055 (10) | −0.0090 (9) |
C8 | 0.0401 (11) | 0.0657 (15) | 0.0344 (11) | −0.0134 (10) | 0.0043 (9) | −0.0124 (10) |
C2 | 0.0499 (12) | 0.0633 (15) | 0.0434 (12) | −0.0009 (11) | 0.0060 (10) | −0.0194 (11) |
C7 | 0.0587 (14) | 0.0504 (13) | 0.0432 (13) | −0.0169 (10) | −0.0008 (11) | 0.0001 (10) |
C9 | 0.0527 (14) | 0.114 (2) | 0.0395 (13) | −0.0197 (14) | 0.0138 (11) | −0.0226 (14) |
C12 | 0.0554 (14) | 0.0638 (16) | 0.0724 (17) | −0.0088 (11) | 0.0059 (12) | −0.0364 (13) |
C5 | 0.0873 (19) | 0.0416 (13) | 0.0670 (17) | −0.0020 (12) | −0.0231 (15) | −0.0115 (12) |
C3 | 0.0666 (16) | 0.083 (2) | 0.0591 (16) | 0.0171 (14) | −0.0077 (13) | −0.0366 (15) |
C4 | 0.091 (2) | 0.0623 (17) | 0.0710 (18) | 0.0233 (15) | −0.0254 (16) | −0.0352 (15) |
C10 | 0.0548 (16) | 0.150 (3) | 0.0654 (19) | −0.0049 (18) | 0.0110 (14) | −0.064 (2) |
C11 | 0.0625 (16) | 0.108 (2) | 0.093 (2) | −0.0015 (16) | 0.0070 (16) | −0.070 (2) |
C14—C19 | 1.384 (3) | C13—C12 | 1.406 (3) |
C14—C15 | 1.388 (3) | C13—C8 | 1.417 (3) |
C14—C20 | 1.497 (3) | C6—C7 | 1.387 (3) |
O3—H101 | 1.06 (3) | C6—C5 | 1.419 (3) |
O1—C20 | 1.272 (2) | C8—C7 | 1.375 (3) |
C16—C17 | 1.383 (3) | C8—C9 | 1.425 (3) |
C16—C15 | 1.390 (3) | C2—C3 | 1.351 (3) |
C16—C21 | 1.482 (3) | C2—H2 | 0.9300 |
O2—C20 | 1.219 (2) | C7—H7 | 0.9300 |
O3—C21 | 1.316 (3) | C9—C10 | 1.345 (4) |
C17—C18 | 1.383 (3) | C9—H9 | 0.9300 |
C17—H17 | 0.9300 | C12—C11 | 1.350 (4) |
O4—C21 | 1.205 (2) | C12—H12 | 0.9300 |
C15—H15 | 0.9300 | C5—C4 | 1.351 (4) |
C19—C18 | 1.374 (3) | C5—H5 | 0.9300 |
C19—H19 | 0.9300 | C3—C4 | 1.397 (4) |
C18—H18 | 0.9300 | C3—H3 | 0.9300 |
N1—C1 | 1.336 (2) | C4—H4 | 0.9300 |
N1—C13 | 1.349 (3) | C10—C11 | 1.409 (5) |
N1—H1 | 0.8600 | C10—H10 | 0.9300 |
C1—C6 | 1.414 (3) | C11—H11 | 0.9300 |
C1—C2 | 1.417 (3) | ||
C19—C14—C15 | 119.20 (19) | C7—C6—C1 | 117.49 (19) |
C19—C14—C20 | 121.34 (18) | C7—C6—C5 | 124.1 (2) |
C15—C14—C20 | 119.43 (18) | C1—C6—C5 | 118.4 (2) |
C21—O3—H101 | 110.1 (16) | C7—C8—C13 | 118.58 (19) |
C17—C16—C15 | 119.10 (18) | C7—C8—C9 | 123.8 (2) |
C17—C16—C21 | 119.63 (18) | C13—C8—C9 | 117.6 (2) |
C15—C16—C21 | 121.26 (18) | C3—C2—C1 | 119.9 (2) |
O2—C20—O1 | 123.42 (19) | C3—C2—H2 | 120.1 |
O2—C20—C14 | 121.59 (19) | C1—C2—H2 | 120.1 |
O1—C20—C14 | 114.95 (17) | C8—C7—C6 | 121.4 (2) |
C18—C17—C16 | 120.23 (19) | C8—C7—H7 | 119.3 |
C18—C17—H17 | 119.9 | C6—C7—H7 | 119.3 |
C16—C17—H17 | 119.9 | C10—C9—C8 | 120.7 (3) |
C14—C15—C16 | 120.72 (18) | C10—C9—H9 | 119.6 |
C14—C15—H15 | 119.6 | C8—C9—H9 | 119.6 |
C16—C15—H15 | 119.6 | C11—C12—C13 | 119.2 (3) |
C18—C19—C14 | 120.33 (19) | C11—C12—H12 | 120.4 |
C18—C19—H19 | 119.8 | C13—C12—H12 | 120.4 |
C14—C19—H19 | 119.8 | C4—C5—C6 | 120.4 (3) |
O4—C21—O3 | 123.1 (2) | C4—C5—H5 | 119.8 |
O4—C21—C16 | 124.1 (2) | C6—C5—H5 | 119.8 |
O3—C21—C16 | 112.81 (17) | C2—C3—C4 | 121.1 (3) |
C19—C18—C17 | 120.4 (2) | C2—C3—H3 | 119.5 |
C19—C18—H18 | 119.8 | C4—C3—H3 | 119.5 |
C17—C18—H18 | 119.8 | C5—C4—C3 | 120.8 (2) |
C1—N1—C13 | 121.77 (17) | C5—C4—H4 | 119.6 |
C1—N1—H1 | 119.1 | C3—C4—H4 | 119.6 |
C13—N1—H1 | 119.1 | C9—C10—C11 | 120.4 (3) |
N1—C1—C6 | 121.01 (19) | C9—C10—H10 | 119.8 |
N1—C1—C2 | 119.56 (19) | C11—C10—H10 | 119.8 |
C6—C1—C2 | 119.43 (19) | C12—C11—C10 | 121.4 (3) |
N1—C13—C12 | 119.6 (2) | C12—C11—H11 | 119.3 |
N1—C13—C8 | 119.74 (19) | C10—C11—H11 | 119.3 |
C12—C13—C8 | 120.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H101···O2i | 1.06 (3) | 1.61 (3) | 2.562 (2) | 147 (3) |
N1—H1···O1ii | 0.86 | 1.70 | 2.553 (2) | 173 |
C19—H19···O4iii | 0.93 | 2.66 | 3.582 (3) | 174 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C13H10N+·C8H5O4− |
Mr | 345.34 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 8.5196 (9), 9.144 (1), 11.386 (4) |
α, β, γ (°) | 69.41 (2), 89.44 (1), 84.22 (1) |
V (Å3) | 825.8 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.50 × 0.25 × 0.15 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3032, 2874, 2054 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.592 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.120, 1.11 |
No. of reflections | 2874 |
No. of parameters | 239 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.27 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1988), CAD-4 Software, TEXSAN (Molecular Structure Corporation, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1993), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H101···O2i | 1.06 (3) | 1.61 (3) | 2.562 (2) | 147 (3) |
N1—H1···O1ii | 0.86 | 1.70 | 2.553 (2) | 173.3 |
C19—H19···O4iii | 0.93 | 2.66 | 3.582 (3) | 174.1 |
Symmetry codes: (i) x−1, y, z; (ii) x, y−1, z; (iii) x+1, y, z. |
Isophthalic acid is an organic dicarboxylic acid which crystallizes in space group P21/c, and forms supramolecular acid chains in its solid-state structure (Derissen, 1974). It is one of the organic acids that we are interested in for our research into the molecular self-assembly of carboxylic acids with N-aromatic complexes. As part of our analysis of the molecular interactions, the structure of the title complex, (I), was determined.
In (I), the cations and anions form a 1:1 cocrystal. The asymmetric unit and atomic numbering scheme of (I) is shown in Fig. 1. Supramolecular acid chains are formed along the a axis via strong O3—H101···O2 and weak C19—H19···O4 hydrogen bonds (Table 2). In addition, acridinium cations are joined to the acid chains (Fig. 2) by N1—H1···O1 hydrogen bonds (Table 2). Proton transfer occurs between the carboxylic acid group and the acridine N atom so that the aromatic N atom is positively charged while the corresponding carboxylic acid group is negatively charged (Table 1). Acridinium cations form infinite stacks along the a axis, the distance between the planes of adjacent acridinium cations being ca 3.5 Å.