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For the new organic salt 1H-imidazol-3-ium 1,4-dioxo-1,4-dihydro­naphthalen-2-olate, C3H5N2+·C10H5O3-, ab initio cal­cul­ations of the gas-phase structures of the lawsonate and imidazolium ions were performed to help in the inter­pretation of the structural features observed. Three different types of hydrogen bond are responsible for the three-dimensional packing of the salt.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113005106/sf3193sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005106/sf3193Isup2.hkl
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S0108270113005106/sf3193Isup3.mol
Supplementary material

CCDC reference: 934613

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

1H-Imidazol-3-ium 1,4-dioxo-1,4-dihydronaphthalen-2-olate top
Crystal data top
C3H5N2+·C10H5O3F(000) = 504
Mr = 242.23Dx = 1.364 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2abCell parameters from 5844 reflections
a = 4.7783 (1) Åθ = 3.9–66.5°
b = 10.7727 (2) ŵ = 0.83 mm1
c = 22.9128 (5) ÅT = 298 K
V = 1179.44 (4) Å3Needle, orange
Z = 40.28 × 0.21 × 0.12 mm
Data collection top
Oxford Xcalibur Gemini Ultra
diffractometer with Atlas detector
2091 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source1966 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.062
Detector resolution: 10.4186 pixels mm-1θmax = 66.6°, θmin = 3.9°
w scansh = 55
Absorption correction: analytical
(CrysAlisPro; Agilent, 2012)
k = 1212
Tmin = 0.861, Tmax = 0.924l = 2727
10612 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.0499P)2 + 0.0821P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.16 e Å3
2091 reflectionsΔρmin = 0.12 e Å3
170 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0032 (6)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with how many Friedel pairs?
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.1 (2)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O40.0065 (3)0.23173 (10)0.36739 (6)0.0582 (4)
O20.6384 (3)0.53669 (11)0.31088 (5)0.0545 (3)
O10.4704 (3)0.67443 (11)0.40191 (5)0.0574 (4)
C90.0664 (4)0.59711 (15)0.48453 (7)0.0435 (4)
H90.14690.67460.49070.052*
C50.0249 (3)0.40963 (14)0.42746 (6)0.0376 (3)
C20.4506 (3)0.49163 (14)0.34490 (7)0.0406 (3)
C30.3269 (4)0.37835 (15)0.33886 (7)0.0454 (4)
H30.3870.32770.30850.054*
C100.1470 (3)0.52621 (13)0.43676 (6)0.0369 (3)
C60.1761 (4)0.36641 (16)0.46604 (7)0.0451 (4)
H60.260.28970.45980.054*
C70.2525 (4)0.43715 (17)0.51387 (7)0.0499 (4)
H70.38440.4070.54010.06*
C80.1327 (4)0.55279 (16)0.52275 (7)0.0492 (4)
H80.18690.60060.55460.059*
C10.3623 (4)0.57319 (13)0.39573 (6)0.0395 (3)
C40.1112 (4)0.33248 (13)0.37613 (7)0.0421 (4)
N10.1010 (3)0.25871 (13)0.18337 (6)0.0481 (4)
N20.1444 (3)0.40035 (13)0.22501 (6)0.0483 (3)
C120.0294 (5)0.45191 (17)0.17647 (8)0.0583 (5)
H120.05270.53310.16360.07*
C130.1243 (5)0.36318 (18)0.15059 (8)0.0596 (5)
H130.22770.37180.11650.072*
C110.0612 (4)0.28451 (16)0.22807 (7)0.0500 (4)
H110.10970.2290.25750.06*
H10.194 (6)0.190 (2)0.1794 (11)0.075*
H20.243 (5)0.445 (2)0.2525 (12)0.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0750 (8)0.0399 (6)0.0598 (7)0.0138 (6)0.0085 (7)0.0117 (5)
O20.0630 (8)0.0473 (6)0.0531 (6)0.0096 (6)0.0226 (6)0.0121 (5)
O10.0714 (8)0.0433 (7)0.0576 (7)0.0156 (6)0.0208 (6)0.0118 (5)
C90.0501 (9)0.0410 (8)0.0394 (8)0.0031 (7)0.0022 (7)0.0066 (6)
C50.0419 (8)0.0351 (7)0.0359 (7)0.0010 (6)0.0039 (6)0.0016 (6)
C20.0435 (8)0.0411 (8)0.0372 (7)0.0013 (7)0.0040 (6)0.0030 (6)
C30.0502 (9)0.0432 (8)0.0428 (8)0.0006 (7)0.0056 (7)0.0138 (6)
C100.0395 (7)0.0363 (8)0.0348 (7)0.0017 (6)0.0010 (6)0.0005 (5)
C60.0484 (9)0.0394 (8)0.0476 (8)0.0042 (7)0.0010 (7)0.0039 (6)
C70.0507 (10)0.0571 (10)0.0417 (8)0.0036 (8)0.0078 (7)0.0052 (7)
C80.0568 (10)0.0526 (9)0.0381 (8)0.0026 (8)0.0065 (8)0.0058 (7)
C10.0437 (8)0.0346 (8)0.0402 (8)0.0001 (6)0.0023 (6)0.0027 (6)
C40.0495 (9)0.0332 (7)0.0436 (8)0.0009 (7)0.0016 (7)0.0028 (6)
N10.0548 (9)0.0459 (7)0.0435 (7)0.0095 (7)0.0004 (7)0.0042 (6)
N20.0590 (8)0.0446 (7)0.0414 (7)0.0064 (7)0.0068 (7)0.0051 (6)
C120.0792 (13)0.0460 (9)0.0496 (9)0.0089 (9)0.0068 (9)0.0064 (7)
C130.0739 (12)0.0606 (10)0.0444 (9)0.0089 (10)0.0185 (9)0.0046 (8)
C110.0615 (10)0.0465 (9)0.0421 (8)0.0023 (8)0.0037 (8)0.0024 (7)
Geometric parameters (Å, º) top
O4—C41.2387 (19)C6—H60.93
O2—C21.284 (2)C7—C81.386 (3)
O1—C11.2151 (19)C7—H70.93
C9—C81.378 (2)C8—H80.93
C9—C101.389 (2)N1—C111.314 (2)
C9—H90.93N1—C131.358 (2)
C5—C61.386 (2)N1—H10.87 (3)
C5—C101.401 (2)N2—C111.312 (2)
C5—C41.498 (2)N2—C121.359 (2)
C2—C31.363 (2)N2—H20.92 (3)
C2—C11.519 (2)C12—C131.343 (3)
C3—C41.427 (2)C12—H120.93
C3—H30.93C13—H130.93
C10—C11.483 (2)C11—H110.93
C6—C71.384 (3)
C8—C9—C10120.10 (15)C7—C8—H8119.9
C8—C9—H9119.9O1—C1—C10121.83 (14)
C10—C9—H9120O1—C1—C2119.37 (14)
C6—C5—C10119.51 (14)C10—C1—C2118.79 (13)
C6—C5—C4120.34 (14)O4—C4—C3122.33 (14)
C10—C5—C4120.15 (14)O4—C4—C5119.21 (15)
O2—C2—C3125.45 (14)C3—C4—C5118.46 (13)
O2—C2—C1116.17 (13)C11—N1—C13107.71 (15)
C3—C2—C1118.37 (14)C11—N1—H1124.3 (17)
C2—C3—C4124.24 (14)C13—N1—H1127.4 (17)
C2—C3—H3117.9C11—N2—C12108.06 (15)
C4—C3—H3117.9C11—N2—H2128.2 (16)
C9—C10—C5119.82 (15)C12—N2—H2123.3 (16)
C9—C10—C1120.29 (14)C13—C12—N2106.94 (16)
C5—C10—C1119.89 (13)C13—C12—H12126.5
C7—C6—C5120.18 (16)N2—C12—H12126.5
C7—C6—H6119.9C12—C13—N1107.51 (16)
C5—C6—H6119.9C12—C13—H13126.2
C6—C7—C8120.17 (16)N1—C13—H13126.2
C6—C7—H7119.9N1—C11—N2109.78 (15)
C8—C7—H7119.9N1—C11—H11125.1
C9—C8—C7120.20 (15)N2—C11—H11125.1
C9—C8—H8119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.87 (3)2.46 (3)2.9726 (19)118 (2)
N1—H1···O2i0.87 (3)1.85 (3)2.6999 (19)166 (3)
N2—H2···O2ii0.92 (3)1.76 (3)2.6658 (17)168 (2)
C12—H12···O4iii0.932.273.182 (2)166
C11—H11···O40.932.573.253 (2)131
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x1, y, z; (iii) x, y+1/2, z+1/2.
Selected bond lengths (Å) for lawsonate taken from X-ray diffraction refinements, for the lawsonate and lawsone forms obtained after ab initio optimization and from the literature top
C1—O1C2—O2C4—O4C3—C4
This work1.220 (2)1.287 (3)1.239 (2)1.423 (3)
Lawsonate, theoreticala1.2511.2741.2821.4117
Lawsone, theoreticala1.2241.3511.2231.465
Lawsone, experimentalb1.207 (2)1.333 (2)1.228 (2)1.450 (3)
Notes: (a) ab initio calculations; (b) Dekkers et al. (1996).
Selected bond lengths (Å) for 1H-imidazolium taken from X-ray diffraction refinements, for 1H-imidazolium obtained after ab initio optimization and from the literature top
N1—C11N2—C11N2—C12C12—C13N1—C13
This work1.314 (2)1.312 (2)1.359 (2)1.343 (3)1.358 (2)
1H-Imidazolium, theoreticala1.3341.3341.3831.3601.383
1H-Imidazole, experimentalb1.349 (18)1.313 (11)1.376 (11)1.360 (14)1.370 (10)
Notes: (a) ab initio calculations; (b) Allen (2002).
 

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