organic compounds
1,4-Diazabicyclo[2.2.2]octane-1,4-diium bis(3-chlorobenzoate)
aInstitute for Materials Chemistry and Engineering, Kyushu University, 6-1, Kasuga-koen, Fukuoka, 816-8580, Japan
*Correspondence e-mail: sato@cm.kyushu-u.ac.jp
In the title salt C6H14N22+·2C7H4ClO2−, two 3-chlorobenzoate (3CBA) anions are bridged by one diprotonated 1,4-diazabicyclo[2.2.2]octane-1,4-diium (H2DABCO2+) dication through N—H⋯O hydrogen bonds. In this way, a trimeric unit is generated, in which the mean planes of the two 3CBA anions are twisted with respect to each other by a dihedral angle of 59.87 (9)°. The trimeric units are linked into a three-dimensional network via weak C—H⋯O interactions.
CCDC reference: 980847
Related literature
For related studies on co-crystals of DABCO and carboxylic acids, see: Arman et al. (2011); Skovsgaard & Bond (2009); Meehan et al. (1997); Rosli et al. (2006); Burchell et al. (2001).
Experimental
Crystal data
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Data collection: CrystalClear (Rigaku, 2008); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 980847
10.1107/S1600536814000610/jj2180sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000610/jj2180Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000610/jj2180Isup3.cml
Colourless crystals of (1) were isolated from slow evaporation of the acetone solution containing DABCO and 3-chlorobenzoic acid in a mole ratio of 1:2 at room temperature.
Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 and 0.99 Å) and were included in the
in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The N bound H-atoms were located in a difference Fourier map, and were refined with a distance restraints of N–H 0.90±0.01 Å; with Uiso(H) set to 1.2Ueq(N).Molecular based compounds constructed via hydrogen bond interaction can give rise to intriguing properties. Here we report an organic
of a salt of 1,4-Diazabicyclo[2.2.2]octane (DABCO) and 3-chlorobenzoic acid. The contains two 3-chlorobenzoate anions and one H2DABCO2+ cation, where the 3-chlorobenzoate anions are connected by the H2DABCO2+ cations by strong intermolecular O–H···N hydrogen bond interactions. The short N···O bond lengths (2.528 (3) and 2.536 (2) Å respectively) suggest possible single-well potential curves of the protons in the trimer unit.For related studies on co-crystals of DABCO and
see: Arman et al. (2011); Skovsgaard & Bond (2009); Meehan et al. (1997); Rosli et al. (2006); Burchell et al. (2001).Data collection: CrystalClear (Rigaku, 2008); cell
CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Displacement ellipsoid plot (50% probability level) of the trimer unit. The dashed lines indicate intermolecular N–H···O hydrogen bonds. | |
Fig. 2. Packing diagram of the title compound viewed along the a axis. The dashed lines indicate intermolecular N–H···O hydrogen bonds forming trimer units. H atoms not involved hydrogen bonding have been omitted for clarity. |
C6H14N22+·2C7H4ClO2− | Z = 2 |
Mr = 425.29 | F(000) = 444 |
Triclinic, P1 | Dx = 1.417 Mg m−3 |
a = 7.332 (4) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 10.512 (6) Å | Cell parameters from 3510 reflections |
c = 13.517 (7) Å | θ = 3.1–27.5° |
α = 79.74 (3)° | µ = 0.36 mm−1 |
β = 76.68 (2)° | T = 123 K |
γ = 85.47 (2)° | Block, colourless |
V = 996.8 (9) Å3 | 0.08 × 0.07 × 0.06 mm |
Rigaku Saturn70 diffractometer | 3671 independent reflections |
Radiation source: Rotating Anode | 2777 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.034 |
ω scans | θmax = 25.5°, θmin = 3.1° |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) | h = −8→8 |
Tmin = 0.874, Tmax = 1.000 | k = −12→12 |
6989 measured reflections | l = −16→16 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0526P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max = 0.001 |
3671 reflections | Δρmax = 0.40 e Å−3 |
253 parameters | Δρmin = −0.33 e Å−3 |
C6H14N22+·2C7H4ClO2− | γ = 85.47 (2)° |
Mr = 425.29 | V = 996.8 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.332 (4) Å | Mo Kα radiation |
b = 10.512 (6) Å | µ = 0.36 mm−1 |
c = 13.517 (7) Å | T = 123 K |
α = 79.74 (3)° | 0.08 × 0.07 × 0.06 mm |
β = 76.68 (2)° |
Rigaku Saturn70 diffractometer | 3671 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008) | 2777 reflections with I > 2σ(I) |
Tmin = 0.874, Tmax = 1.000 | Rint = 0.034 |
6989 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 0.91 | Δρmax = 0.40 e Å−3 |
3671 reflections | Δρmin = −0.33 e Å−3 |
253 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 | ||
Cl1 | 0.85741 (7) | 0.29946 (5) | 0.56505 (4) | 0.02963 (16) | |
Cl2 | −0.96963 (7) | −0.46471 (5) | 0.18722 (4) | 0.03041 (16) | |
O1 | 0.33887 (19) | 0.09113 (13) | 0.42587 (10) | 0.0247 (3) | |
O2 | 0.26536 (19) | 0.24510 (13) | 0.30319 (11) | 0.0277 (3) | |
O3 | −0.40110 (18) | −0.19373 (13) | 0.18759 (10) | 0.0209 (3) | |
O4 | −0.22174 (19) | −0.15730 (15) | 0.02822 (10) | 0.0320 (4) | |
N1 | −0.1723 (2) | −0.05291 (14) | 0.22871 (11) | 0.0163 (4) | |
H1N | −0.2524 | −0.1042 | 0.2147 | 0.020* | |
N2 | 0.0517 (2) | 0.08989 (15) | 0.26718 (11) | 0.0170 (4) | |
H2N | 0.1317 | 0.1413 | 0.2812 | 0.020* | |
C1 | 0.4754 (2) | 0.29730 (18) | 0.39639 (13) | 0.0152 (4) | |
C2 | 0.4815 (3) | 0.42300 (18) | 0.34315 (14) | 0.0183 (4) | |
H2 | 0.3996 | 0.4506 | 0.2977 | 0.022* | |
C3 | 0.6052 (3) | 0.50894 (19) | 0.35524 (14) | 0.0204 (4) | |
H3 | 0.6092 | 0.5944 | 0.3175 | 0.024* | |
C4 | 0.7235 (3) | 0.46978 (19) | 0.42271 (14) | 0.0193 (4) | |
H4 | 0.8105 | 0.5273 | 0.4309 | 0.023* | |
C5 | 0.7124 (2) | 0.34535 (19) | 0.47776 (14) | 0.0178 (4) | |
C6 | 0.5904 (2) | 0.25831 (18) | 0.46641 (14) | 0.0168 (4) | |
H6 | 0.5848 | 0.1735 | 0.5054 | 0.020* | |
C7 | 0.3501 (2) | 0.20080 (18) | 0.37673 (14) | 0.0166 (4) | |
C8 | −0.4958 (3) | −0.27845 (17) | 0.05760 (14) | 0.0165 (4) | |
C9 | −0.6506 (2) | −0.33291 (17) | 0.12918 (14) | 0.0163 (4) | |
H9 | −0.6695 | −0.3249 | 0.1998 | 0.020* | |
C10 | −0.7755 (3) | −0.39815 (18) | 0.09679 (15) | 0.0183 (4) | |
C11 | −0.7508 (3) | −0.41311 (19) | −0.00502 (15) | 0.0212 (4) | |
H11 | −0.8381 | −0.4587 | −0.0262 | 0.025* | |
C12 | −0.5961 (3) | −0.36021 (18) | −0.07544 (15) | 0.0213 (4) | |
H12 | −0.5769 | −0.3698 | −0.1457 | 0.026* | |
C13 | −0.4691 (3) | −0.29346 (18) | −0.04470 (14) | 0.0193 (4) | |
H13 | −0.3633 | −0.2579 | −0.0938 | 0.023* | |
C14 | −0.3593 (3) | −0.20410 (18) | 0.09103 (14) | 0.0191 (4) | |
C15 | −0.1980 (3) | 0.08017 (18) | 0.17522 (15) | 0.0211 (4) | |
H15A | −0.3308 | 0.1102 | 0.1950 | 0.025* | |
H15B | −0.1653 | 0.0822 | 0.0997 | 0.025* | |
C16 | −0.0712 (3) | 0.16953 (18) | 0.20515 (15) | 0.0210 (4) | |
H16A | 0.0062 | 0.2189 | 0.1423 | 0.025* | |
H16B | −0.1488 | 0.2319 | 0.2457 | 0.025* | |
C17 | 0.0218 (2) | −0.10165 (19) | 0.19240 (15) | 0.0200 (4) | |
H17A | 0.0442 | −0.1082 | 0.1184 | 0.024* | |
H17B | 0.0414 | −0.1890 | 0.2312 | 0.024* | |
C18 | 0.1599 (3) | −0.00838 (18) | 0.20868 (14) | 0.0188 (4) | |
H18A | 0.2499 | −0.0569 | 0.2474 | 0.023* | |
H18B | 0.2315 | 0.0344 | 0.1412 | 0.023* | |
C19 | −0.2115 (3) | −0.05460 (19) | 0.34127 (14) | 0.0190 (4) | |
H19A | −0.2063 | −0.1448 | 0.3777 | 0.023* | |
H19B | −0.3385 | −0.0165 | 0.3649 | 0.023* | |
C20 | −0.0641 (3) | 0.02409 (18) | 0.36553 (14) | 0.0187 (4) | |
H20A | −0.1270 | 0.0892 | 0.4081 | 0.022* | |
H20B | 0.0169 | −0.0340 | 0.4048 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0312 (3) | 0.0291 (3) | 0.0341 (3) | −0.0036 (2) | −0.0212 (2) | −0.0007 (2) |
Cl2 | 0.0256 (3) | 0.0346 (3) | 0.0307 (3) | −0.0156 (2) | −0.0003 (2) | −0.0061 (2) |
O1 | 0.0320 (8) | 0.0181 (8) | 0.0259 (8) | −0.0076 (6) | −0.0121 (6) | 0.0020 (6) |
O2 | 0.0377 (9) | 0.0250 (8) | 0.0254 (8) | −0.0111 (6) | −0.0205 (7) | 0.0046 (6) |
O3 | 0.0248 (8) | 0.0236 (8) | 0.0153 (7) | −0.0077 (6) | −0.0037 (6) | −0.0042 (6) |
O4 | 0.0295 (9) | 0.0475 (10) | 0.0191 (8) | −0.0213 (7) | −0.0021 (6) | −0.0013 (7) |
N1 | 0.0186 (9) | 0.0145 (8) | 0.0179 (8) | −0.0035 (6) | −0.0077 (7) | −0.0025 (7) |
N2 | 0.0176 (9) | 0.0171 (9) | 0.0181 (8) | −0.0045 (7) | −0.0074 (7) | −0.0014 (7) |
C1 | 0.0157 (10) | 0.0172 (10) | 0.0124 (9) | −0.0011 (7) | −0.0011 (7) | −0.0040 (8) |
C2 | 0.0199 (11) | 0.0226 (11) | 0.0123 (9) | −0.0002 (8) | −0.0043 (8) | −0.0017 (8) |
C3 | 0.0258 (11) | 0.0171 (10) | 0.0165 (10) | −0.0039 (8) | −0.0021 (8) | 0.0000 (8) |
C4 | 0.0186 (10) | 0.0217 (11) | 0.0181 (10) | −0.0062 (8) | −0.0018 (8) | −0.0047 (8) |
C5 | 0.0159 (10) | 0.0228 (11) | 0.0160 (10) | −0.0003 (8) | −0.0058 (8) | −0.0040 (8) |
C6 | 0.0172 (10) | 0.0169 (10) | 0.0153 (9) | −0.0014 (8) | −0.0020 (7) | −0.0018 (8) |
C7 | 0.0156 (10) | 0.0203 (11) | 0.0139 (10) | −0.0024 (8) | −0.0022 (7) | −0.0037 (8) |
C8 | 0.0186 (10) | 0.0126 (10) | 0.0183 (10) | 0.0009 (7) | −0.0055 (8) | −0.0014 (8) |
C9 | 0.0177 (10) | 0.0162 (10) | 0.0153 (10) | 0.0009 (8) | −0.0030 (8) | −0.0046 (8) |
C10 | 0.0169 (10) | 0.0165 (10) | 0.0213 (10) | −0.0013 (8) | −0.0037 (8) | −0.0028 (8) |
C11 | 0.0228 (11) | 0.0194 (11) | 0.0262 (11) | 0.0000 (8) | −0.0119 (9) | −0.0080 (9) |
C12 | 0.0272 (12) | 0.0227 (11) | 0.0158 (10) | 0.0016 (8) | −0.0085 (8) | −0.0042 (8) |
C13 | 0.0221 (11) | 0.0194 (10) | 0.0151 (10) | −0.0003 (8) | −0.0042 (8) | 0.0008 (8) |
C14 | 0.0199 (11) | 0.0170 (10) | 0.0206 (11) | −0.0031 (8) | −0.0064 (8) | 0.0003 (8) |
C15 | 0.0228 (11) | 0.0183 (10) | 0.0232 (11) | −0.0010 (8) | −0.0108 (8) | 0.0016 (9) |
C16 | 0.0253 (11) | 0.0171 (10) | 0.0218 (11) | −0.0016 (8) | −0.0103 (8) | 0.0009 (8) |
C17 | 0.0153 (11) | 0.0236 (11) | 0.0217 (10) | 0.0019 (8) | −0.0037 (8) | −0.0068 (9) |
C18 | 0.0165 (10) | 0.0212 (11) | 0.0184 (10) | −0.0007 (8) | −0.0029 (8) | −0.0034 (8) |
C19 | 0.0203 (11) | 0.0216 (11) | 0.0145 (10) | −0.0040 (8) | −0.0022 (8) | −0.0017 (8) |
C20 | 0.0225 (11) | 0.0203 (10) | 0.0135 (10) | −0.0023 (8) | −0.0040 (8) | −0.0020 (8) |
Cl1—C5 | 1.747 (2) | C8—C9 | 1.397 (3) |
Cl2—C10 | 1.749 (2) | C8—C14 | 1.508 (3) |
O1—C7 | 1.222 (2) | C9—C10 | 1.375 (2) |
O2—C7 | 1.290 (2) | C9—H9 | 0.9500 |
O3—C14 | 1.292 (2) | C10—C11 | 1.382 (3) |
O4—C14 | 1.231 (2) | C11—C12 | 1.384 (3) |
N1—C15 | 1.475 (2) | C11—H11 | 0.9500 |
N1—C19 | 1.479 (2) | C12—C13 | 1.385 (2) |
N1—C17 | 1.478 (2) | C12—H12 | 0.9500 |
N1—H1N | 0.9000 | C13—H13 | 0.9500 |
N2—C18 | 1.481 (2) | C15—C16 | 1.536 (3) |
N2—C16 | 1.481 (2) | C15—H15A | 0.9900 |
N2—C20 | 1.487 (2) | C15—H15B | 0.9900 |
N2—H2N | 0.9000 | C16—H16A | 0.9900 |
C1—C2 | 1.386 (3) | C16—H16B | 0.9900 |
C1—C6 | 1.396 (3) | C17—C18 | 1.540 (2) |
C1—C7 | 1.516 (2) | C17—H17A | 0.9900 |
C2—C3 | 1.384 (3) | C17—H17B | 0.9900 |
C2—H2 | 0.9500 | C18—H18A | 0.9900 |
C3—C4 | 1.388 (3) | C18—H18B | 0.9900 |
C3—H3 | 0.9500 | C19—C20 | 1.537 (2) |
C4—C5 | 1.383 (3) | C19—H19A | 0.9900 |
C4—H4 | 0.9500 | C19—H19B | 0.9900 |
C5—C6 | 1.379 (3) | C20—H20A | 0.9900 |
C6—H6 | 0.9500 | C20—H20B | 0.9900 |
C8—C13 | 1.387 (3) | ||
C15—N1—C19 | 109.80 (15) | C13—C12—C11 | 120.80 (18) |
C15—N1—C17 | 109.77 (15) | C13—C12—H12 | 119.6 |
C19—N1—C17 | 109.86 (14) | C11—C12—H12 | 119.6 |
C15—N1—H1N | 109.2 | C12—C13—C8 | 120.19 (18) |
C19—N1—H1N | 109.2 | C12—C13—H13 | 119.9 |
C17—N1—H1N | 109.1 | C8—C13—H13 | 119.9 |
C18—N2—C16 | 109.80 (14) | O4—C14—O3 | 124.69 (17) |
C18—N2—C20 | 109.46 (15) | O4—C14—C8 | 120.50 (17) |
C16—N2—C20 | 109.79 (15) | O3—C14—C8 | 114.81 (16) |
C18—N2—H2N | 109.3 | N1—C15—C16 | 109.14 (15) |
C16—N2—H2N | 109.3 | N1—C15—H15A | 109.9 |
C20—N2—H2N | 109.2 | C16—C15—H15A | 109.9 |
C2—C1—C6 | 119.49 (17) | N1—C15—H15B | 109.9 |
C2—C1—C7 | 120.69 (17) | C16—C15—H15B | 109.9 |
C6—C1—C7 | 119.79 (17) | H15A—C15—H15B | 108.3 |
C3—C2—C1 | 121.01 (18) | N2—C16—C15 | 108.98 (15) |
C3—C2—H2 | 119.5 | N2—C16—H16A | 109.9 |
C1—C2—H2 | 119.5 | C15—C16—H16A | 109.9 |
C2—C3—C4 | 119.77 (18) | N2—C16—H16B | 109.9 |
C2—C3—H3 | 120.1 | C15—C16—H16B | 109.9 |
C4—C3—H3 | 120.1 | H16A—C16—H16B | 108.3 |
C5—C4—C3 | 118.74 (18) | N1—C17—C18 | 109.31 (15) |
C5—C4—H4 | 120.6 | N1—C17—H17A | 109.8 |
C3—C4—H4 | 120.6 | C18—C17—H17A | 109.8 |
C6—C5—C4 | 122.26 (18) | N1—C17—H17B | 109.8 |
C6—C5—Cl1 | 119.69 (15) | C18—C17—H17B | 109.8 |
C4—C5—Cl1 | 118.05 (14) | H17A—C17—H17B | 108.3 |
C5—C6—C1 | 118.67 (18) | N2—C18—C17 | 108.61 (14) |
C5—C6—H6 | 120.7 | N2—C18—H18A | 110.0 |
C1—C6—H6 | 120.7 | C17—C18—H18A | 110.0 |
O1—C7—O2 | 125.20 (17) | N2—C18—H18B | 110.0 |
O1—C7—C1 | 121.13 (17) | C17—C18—H18B | 110.0 |
O2—C7—C1 | 113.64 (17) | H18A—C18—H18B | 108.3 |
C13—C8—C9 | 119.23 (17) | N1—C19—C20 | 108.85 (14) |
C13—C8—C14 | 120.32 (17) | N1—C19—H19A | 109.9 |
C9—C8—C14 | 120.45 (16) | C20—C19—H19A | 109.9 |
C10—C9—C8 | 119.57 (17) | N1—C19—H19B | 109.9 |
C10—C9—H9 | 120.2 | C20—C19—H19B | 109.9 |
C8—C9—H9 | 120.2 | H19A—C19—H19B | 108.3 |
C9—C10—C11 | 121.69 (18) | N2—C20—C19 | 109.05 (14) |
C9—C10—Cl2 | 119.01 (15) | N2—C20—H20A | 109.9 |
C11—C10—Cl2 | 119.29 (14) | C19—C20—H20A | 109.9 |
C10—C11—C12 | 118.52 (17) | N2—C20—H20B | 109.9 |
C10—C11—H11 | 120.7 | C19—C20—H20B | 109.9 |
C12—C11—H11 | 120.7 | H20A—C20—H20B | 108.3 |
C6—C1—C2—C3 | 2.6 (3) | C9—C8—C13—C12 | 0.9 (3) |
C7—C1—C2—C3 | −175.35 (16) | C14—C8—C13—C12 | −179.08 (17) |
C1—C2—C3—C4 | −0.9 (3) | C13—C8—C14—O4 | −0.8 (3) |
C2—C3—C4—C5 | −1.0 (3) | C9—C8—C14—O4 | 179.18 (18) |
C3—C4—C5—C6 | 1.3 (3) | C13—C8—C14—O3 | 178.35 (17) |
C3—C4—C5—Cl1 | −178.13 (14) | C9—C8—C14—O3 | −1.6 (3) |
C4—C5—C6—C1 | 0.4 (3) | C19—N1—C15—C16 | 56.50 (19) |
Cl1—C5—C6—C1 | 179.80 (13) | C17—N1—C15—C16 | −64.36 (19) |
C2—C1—C6—C5 | −2.3 (3) | C18—N2—C16—C15 | 56.32 (19) |
C7—C1—C6—C5 | 175.65 (15) | C20—N2—C16—C15 | −64.07 (18) |
C2—C1—C7—O1 | −177.41 (18) | N1—C15—C16—N2 | 7.0 (2) |
C6—C1—C7—O1 | 4.6 (3) | C15—N1—C17—C18 | 56.14 (19) |
C2—C1—C7—O2 | 4.5 (2) | C19—N1—C17—C18 | −64.69 (19) |
C6—C1—C7—O2 | −173.43 (16) | C16—N2—C18—C17 | −64.37 (19) |
C13—C8—C9—C10 | −1.3 (3) | C20—N2—C18—C17 | 56.22 (19) |
C14—C8—C9—C10 | 178.71 (17) | N1—C17—C18—N2 | 7.0 (2) |
C8—C9—C10—C11 | 0.9 (3) | C15—N1—C19—C20 | −65.01 (18) |
C8—C9—C10—Cl2 | −179.50 (14) | C17—N1—C19—C20 | 55.80 (19) |
C9—C10—C11—C12 | −0.2 (3) | C18—N2—C20—C19 | −65.10 (19) |
Cl2—C10—C11—C12 | −179.78 (15) | C16—N2—C20—C19 | 55.49 (19) |
C10—C11—C12—C13 | −0.2 (3) | N1—C19—C20—N2 | 7.6 (2) |
C11—C12—C13—C8 | −0.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3 | 0.90 | 1.64 | 2.536 (2) | 178 |
N2—H2N···O2 | 0.90 | 1.63 | 2.528 (3) | 175 |
C3—H3···O3i | 0.95 | 2.59 | 3.523 (3) | 169 |
C18—H18B···O4ii | 0.99 | 2.43 | 3.311 (3) | 147 |
C19—H19B···O1iii | 0.99 | 2.56 | 3.552 (3) | 178 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y, −z; (iii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O3 | 0.90 | 1.64 | 2.536 (2) | 178 |
N2—H2N···O2 | 0.90 | 1.63 | 2.528 (3) | 175 |
C3—H3···O3i | 0.95 | 2.59 | 3.523 (3) | 169 |
C18—H18B···O4ii | 0.99 | 2.43 | 3.311 (3) | 147 |
C19—H19B···O1iii | 0.99 | 2.56 | 3.552 (3) | 177.6 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y, −z; (iii) x−1, y, z. |
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Molecular based compounds constructed via hydrogen bond interaction can give rise to intriguing properties. Here we report an organic co-crystal of a salt of 1,4-Diazabicyclo[2.2.2]octane (DABCO) and 3-chlorobenzoic acid. The asymmetric unit contains two 3-chlorobenzoate anions and one H2DABCO2+ cation, where the 3-chlorobenzoate anions are connected by the H2DABCO2+ cations by strong intermolecular O–H···N hydrogen bond interactions. The short N···O bond lengths (2.528 (3) and 2.536 (2) Å respectively) suggest possible single-well potential curves of the protons in the trimer unit.