metal-organic compounds
Bis(dihydrogen norfloxacinium) tri-μ2-chlorido-bis[trichloridobismuthate(III)] chloride dihydrate
aInstitute of Chemistry, FEB RAS, Prospekt 100-letiya Vladivostoka 159, Vladivostok 690022, Russian Federation
*Correspondence e-mail: gerasimenko@ich.dvo.ru
The title compound, {systematic name: (3-carboxy-1-ethyl-6-fluoro-7-piperazin-4-ium-1-yl-1H-quinolin-4-ylidene)oxonium tri-μ2-chlorido-bis[trichloridobismuthate(III)] chloride dihydrate], (C16H20FN3O3)2[Bi2Cl9]Cl·2H2O, is composed of [Bi2Cl9]3− anions lying on crystallographic twofold rotation axes, Cl− anions also on twofold axes, C16H20FN3O32+ cations, and water molecules. The BiIII is a distorted octahedron and two such octahedra share a triangular face to form the complex anion. There are three short terminal Bi—Cl bonds [2.5471 (6)–2.5781(5 Å] and three longer bridging bonds [2.8599 (5)–2.9984 (6) Å] in each octahedron. Anions, cations and water molecules are linked by hydrogen bonds to form a three-dimensional network. There are also π–π stacking interactions between quinoline ring systems, with an interplanar distance of 3.27 (1) Å.
Related literature
For the Cambridge Structural Database (Version 5.28) used to identify related structures, see: Allen (2002).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: publCIF (Version 1.9.0; Westrip, 2008).
Supporting information
10.1107/S1600536808001244/cf2178sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808001244/cf2178Isup2.hkl
Bi(OH)3 (0.052 g, 0.2 mmol) was reacted with nfH (0.066 g, 0.2 mmol) in an aqueous solution of HCl (21%, 20 ml). Yellow crystals were obtained after evaporation for 72 h at room temperature.
H atoms (for H2O) were located in a difference map and refined with Uiso(H) = 1.5Ueq(O) and the O—H distances were restrained to be similar. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.94, 0.97 and 0.98 Å; N—H = 0.91 Å and O—H = 0.83 Å. All H atoms were refined with Uiso set to 1.2 or 1.5 times Ueq of the parent atom. The maximum peak and the deepest hole are located 0.77 Å and 1.33 Å from Bi, respectively.
Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Version 1.9.0; Westrip, 2008).Fig. 1. A view of the dinuclear [Bi2Cl9]3- complex, with displacement ellipsoids drawn at the 50% probability level. [Symmetry code: (i) -x, y, 1/2 - z.] | |
Fig. 2. A view of the nfH32+ canion, with displacement ellipsoids drawn at the 50% probability level. The intramolecular hydrogen bond is shown as a dashed line. | |
Fig. 3. Fragment of the zigzag chain formed from water molecules, chloride anions and nfH32+ canions, with hydrogen bonds shown as dashed lines. | |
Fig. 4. The crystal structure of the title compound viewed along the c axis. Dashed lines represent hydrogen bonds. |
(C16H20FN3O3)2[Bi2Cl9]Cl·2H2O | F(000) = 2784 |
Mr = 1451.19 | Dx = 2.093 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.9109 (12) Å | Cell parameters from 951 reflections |
b = 22.7104 (19) Å | θ = 3.9–30.6° |
c = 14.5964 (12) Å | µ = 8.27 mm−1 |
β = 92.798 (2)° | T = 203 K |
V = 4605.8 (7) Å3 | Prism, yellow |
Z = 4 | 0.27 × 0.22 × 0.17 mm |
Bruker SMART 1000 CCD area-detector diffractometer | 6987 independent reflections |
Radiation source: fine-focus sealed tube | 6081 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 8.33 pixels mm-1 | θmax = 31.5°, θmin = 3.6° |
ϕ and ω scans | h = −20→15 |
Absorption correction: gaussian (SADABS; Bruker, 2003) | k = −31→32 |
Tmin = 0.180, Tmax = 0.334 | l = −20→14 |
16736 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.025 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0269P)2 + 1.9407P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.012 |
6987 reflections | Δρmax = 1.58 e Å−3 |
282 parameters | Δρmin = −0.84 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.000362 (17) |
(C16H20FN3O3)2[Bi2Cl9]Cl·2H2O | V = 4605.8 (7) Å3 |
Mr = 1451.19 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 13.9109 (12) Å | µ = 8.27 mm−1 |
b = 22.7104 (19) Å | T = 203 K |
c = 14.5964 (12) Å | 0.27 × 0.22 × 0.17 mm |
β = 92.798 (2)° |
Bruker SMART 1000 CCD area-detector diffractometer | 6987 independent reflections |
Absorption correction: gaussian (SADABS; Bruker, 2003) | 6081 reflections with I > 2σ(I) |
Tmin = 0.180, Tmax = 0.334 | Rint = 0.031 |
16736 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 1 restraint |
wR(F2) = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 1.58 e Å−3 |
6987 reflections | Δρmin = −0.84 e Å−3 |
282 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 | ||
Bi1 | 0.125399 (5) | 0.231497 (3) | 0.205209 (5) | 0.01711 (2) | |
Cl1 | 0.0000 | 0.13708 (3) | 0.2500 | 0.02433 (15) | |
Cl2 | 0.06458 (4) | 0.26380 (2) | 0.38711 (4) | 0.02637 (11) | |
Cl3 | 0.16112 (4) | 0.18802 (2) | 0.04945 (3) | 0.02670 (11) | |
Cl4 | 0.27484 (4) | 0.18468 (3) | 0.28222 (4) | 0.03193 (13) | |
Cl5 | 0.20122 (4) | 0.33350 (2) | 0.18044 (4) | 0.03441 (13) | |
Cl6 | 0.5000 | 0.48180 (3) | 0.2500 | 0.0356 (2) | |
F1 | 0.75259 (8) | 0.46603 (5) | 0.43340 (9) | 0.0275 (3) | |
O1 | 1.25735 (10) | 0.45323 (6) | 0.28600 (10) | 0.0262 (3) | |
O2 | 1.32428 (11) | 0.54074 (6) | 0.32107 (12) | 0.0317 (4) | |
H2 | 1.3714 | 0.5259 | 0.2970 | 0.048* | |
O3 | 1.08058 (10) | 0.43447 (6) | 0.32403 (10) | 0.0225 (3) | |
H3 | 1.1348 | 0.4259 | 0.3067 | 0.034* | |
O4 | 0.42564 (14) | 0.36716 (10) | 0.14845 (15) | 0.0632 (6) | |
H4A | 0.3777 (12) | 0.3561 (14) | 0.152 (3) | 0.076* | |
H4B | 0.429 (3) | 0.3968 (8) | 0.165 (2) | 0.076* | |
N1 | 1.07419 (11) | 0.60588 (7) | 0.41452 (11) | 0.0167 (3) | |
N2 | 0.73624 (11) | 0.58287 (7) | 0.48464 (11) | 0.0200 (4) | |
N3 | 0.56019 (12) | 0.64241 (8) | 0.52271 (13) | 0.0275 (4) | |
H3A | 0.5558 | 0.6702 | 0.4778 | 0.033* | |
H3B | 0.5084 | 0.6464 | 0.5579 | 0.033* | |
C1 | 1.15439 (13) | 0.58404 (8) | 0.38258 (13) | 0.0184 (4) | |
H1 | 1.2091 | 0.6083 | 0.3820 | 0.022* | |
C2 | 1.16090 (13) | 0.52665 (8) | 0.34983 (13) | 0.0179 (4) | |
C3 | 1.08010 (13) | 0.48980 (8) | 0.35148 (13) | 0.0172 (4) | |
C4 | 0.99316 (13) | 0.51308 (8) | 0.38424 (13) | 0.0167 (4) | |
C5 | 0.91002 (14) | 0.47809 (8) | 0.38934 (13) | 0.0192 (4) | |
H5 | 0.9105 | 0.4386 | 0.3700 | 0.023* | |
C6 | 0.82924 (13) | 0.50185 (8) | 0.42245 (13) | 0.0193 (4) | |
C7 | 0.82172 (13) | 0.56183 (8) | 0.45095 (13) | 0.0180 (4) | |
C8 | 0.90503 (13) | 0.59551 (8) | 0.44819 (13) | 0.0176 (4) | |
H8 | 0.9043 | 0.6348 | 0.4684 | 0.021* | |
C9 | 0.99058 (13) | 0.57178 (8) | 0.41560 (13) | 0.0170 (4) | |
C10 | 1.07597 (14) | 0.66786 (8) | 0.44871 (14) | 0.0211 (4) | |
H10A | 1.1427 | 0.6794 | 0.4639 | 0.025* | |
H10B | 1.0406 | 0.6701 | 0.5050 | 0.025* | |
C11 | 1.03232 (16) | 0.71041 (9) | 0.37950 (16) | 0.0282 (5) | |
H11A | 1.0642 | 0.7065 | 0.3222 | 0.042* | |
H11B | 1.0403 | 0.7503 | 0.4023 | 0.042* | |
H11C | 0.9643 | 0.7019 | 0.3694 | 0.042* | |
C12 | 1.25206 (14) | 0.50349 (9) | 0.31606 (14) | 0.0213 (4) | |
C13 | 0.73860 (14) | 0.64186 (9) | 0.52505 (14) | 0.0228 (4) | |
H13A | 0.7405 | 0.6714 | 0.4763 | 0.027* | |
H13B | 0.7969 | 0.6463 | 0.5650 | 0.027* | |
C14 | 0.65017 (15) | 0.65186 (10) | 0.58046 (16) | 0.0270 (5) | |
H14A | 0.6516 | 0.6247 | 0.6327 | 0.032* | |
H14B | 0.6511 | 0.6921 | 0.6045 | 0.032* | |
C15 | 0.55900 (15) | 0.58264 (10) | 0.48029 (16) | 0.0284 (5) | |
H15A | 0.5012 | 0.5782 | 0.4397 | 0.034* | |
H15B | 0.5572 | 0.5526 | 0.5284 | 0.034* | |
C16 | 0.64805 (14) | 0.57405 (10) | 0.42577 (14) | 0.0254 (5) | |
H16A | 0.6480 | 0.5342 | 0.4001 | 0.031* | |
H16B | 0.6471 | 0.6021 | 0.3748 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.01352 (3) | 0.01870 (3) | 0.01912 (3) | −0.00108 (2) | 0.00093 (2) | −0.00093 (2) |
Cl1 | 0.0228 (3) | 0.0167 (3) | 0.0330 (4) | 0.000 | −0.0039 (3) | 0.000 |
Cl2 | 0.0241 (2) | 0.0284 (2) | 0.0269 (2) | −0.00434 (18) | 0.00425 (19) | −0.00849 (19) |
Cl3 | 0.0214 (2) | 0.0372 (2) | 0.0214 (2) | 0.00634 (19) | −0.00045 (18) | −0.0049 (2) |
Cl4 | 0.0214 (2) | 0.0466 (3) | 0.0275 (3) | 0.0063 (2) | −0.00225 (19) | 0.0042 (2) |
Cl5 | 0.0332 (3) | 0.0226 (2) | 0.0480 (3) | −0.0083 (2) | 0.0071 (2) | −0.0018 (2) |
Cl6 | 0.0209 (3) | 0.0200 (3) | 0.0671 (5) | 0.000 | 0.0154 (3) | 0.000 |
F1 | 0.0198 (5) | 0.0281 (6) | 0.0351 (7) | −0.0095 (5) | 0.0049 (5) | −0.0042 (5) |
O1 | 0.0213 (7) | 0.0252 (7) | 0.0324 (8) | 0.0038 (6) | 0.0036 (6) | −0.0085 (6) |
O2 | 0.0182 (7) | 0.0258 (7) | 0.0523 (10) | −0.0008 (6) | 0.0126 (6) | −0.0086 (7) |
O3 | 0.0206 (6) | 0.0201 (6) | 0.0267 (7) | 0.0011 (5) | 0.0017 (6) | −0.0056 (5) |
O4 | 0.0324 (9) | 0.0866 (13) | 0.0726 (13) | −0.0253 (9) | 0.0216 (9) | −0.0498 (11) |
N1 | 0.0134 (6) | 0.0167 (6) | 0.0199 (7) | −0.0018 (5) | 0.0008 (6) | −0.0012 (6) |
N2 | 0.0109 (7) | 0.0268 (7) | 0.0223 (8) | 0.0003 (6) | −0.0003 (6) | −0.0025 (7) |
N3 | 0.0158 (7) | 0.0310 (8) | 0.0360 (10) | 0.0057 (7) | 0.0045 (7) | 0.0098 (8) |
C1 | 0.0142 (8) | 0.0213 (8) | 0.0196 (9) | −0.0020 (6) | 0.0008 (7) | 0.0016 (7) |
C2 | 0.0151 (8) | 0.0208 (8) | 0.0178 (8) | 0.0006 (7) | 0.0013 (7) | −0.0004 (7) |
C3 | 0.0183 (8) | 0.0163 (7) | 0.0167 (8) | 0.0006 (6) | −0.0004 (7) | 0.0005 (7) |
C4 | 0.0157 (8) | 0.0186 (8) | 0.0159 (8) | −0.0006 (6) | −0.0002 (6) | −0.0002 (7) |
C5 | 0.0194 (8) | 0.0209 (8) | 0.0171 (8) | −0.0032 (7) | −0.0002 (7) | −0.0016 (7) |
C6 | 0.0148 (8) | 0.0240 (8) | 0.0189 (9) | −0.0045 (7) | −0.0002 (7) | −0.0007 (7) |
C7 | 0.0159 (8) | 0.0211 (8) | 0.0168 (8) | −0.0015 (7) | −0.0016 (7) | 0.0003 (7) |
C8 | 0.0165 (8) | 0.0183 (8) | 0.0180 (8) | 0.0006 (6) | 0.0001 (7) | −0.0016 (7) |
C9 | 0.0141 (8) | 0.0200 (8) | 0.0168 (8) | −0.0002 (6) | −0.0004 (6) | 0.0006 (7) |
C10 | 0.0171 (8) | 0.0192 (8) | 0.0273 (10) | −0.0027 (7) | 0.0027 (7) | −0.0087 (7) |
C11 | 0.0277 (10) | 0.0224 (9) | 0.0348 (12) | 0.0019 (8) | 0.0045 (9) | 0.0004 (9) |
C12 | 0.0200 (9) | 0.0248 (9) | 0.0191 (9) | 0.0019 (7) | 0.0008 (7) | 0.0007 (7) |
C13 | 0.0175 (8) | 0.0232 (9) | 0.0277 (10) | 0.0006 (7) | 0.0029 (7) | −0.0024 (8) |
C14 | 0.0199 (9) | 0.0276 (9) | 0.0338 (11) | 0.0043 (8) | 0.0048 (8) | 0.0006 (9) |
C15 | 0.0157 (9) | 0.0325 (10) | 0.0367 (12) | 0.0009 (8) | −0.0014 (8) | 0.0053 (9) |
C16 | 0.0169 (9) | 0.0361 (10) | 0.0229 (10) | −0.0016 (8) | −0.0028 (7) | 0.0020 (8) |
Bi1—Bi1i | 3.7851 (3) | C1—H1 | 0.940 |
Bi1—Cl4 | 2.5471 (6) | C2—C3 | 1.402 (3) |
Bi1—Cl3 | 2.5497 (5) | C2—C12 | 1.479 (3) |
Bi1—Cl5 | 2.5781 (5) | C3—C4 | 1.424 (3) |
Bi1—Cl1 | 2.8599 (5) | C4—C5 | 1.408 (3) |
Bi1—Cl2 | 2.9194 (6) | C4—C9 | 1.411 (3) |
Bi1—Cl2i | 2.9984 (6) | C5—C6 | 1.357 (3) |
Cl1—Bi1i | 2.8599 (5) | C5—H5 | 0.940 |
Cl2—Bi1i | 2.9984 (6) | C6—C7 | 1.430 (3) |
F1—C6 | 1.357 (2) | C7—C8 | 1.391 (3) |
O1—C12 | 1.226 (2) | C8—C9 | 1.410 (3) |
O2—C12 | 1.313 (2) | C8—H8 | 0.940 |
O2—H2 | 0.830 | C10—C11 | 1.504 (3) |
O3—C3 | 1.319 (2) | C10—H10A | 0.980 |
O3—H3 | 0.830 | C10—H10B | 0.980 |
O4—H4A | 0.715 (18) | C11—H11A | 0.970 |
O4—H4B | 0.717 (19) | C11—H11B | 0.970 |
N1—C1 | 1.326 (2) | C11—H11C | 0.970 |
N1—C9 | 1.398 (2) | C13—C14 | 1.522 (3) |
N1—C10 | 1.493 (2) | C13—H13A | 0.980 |
N2—C7 | 1.393 (2) | C13—H13B | 0.980 |
N2—C13 | 1.464 (3) | C14—H14A | 0.980 |
N2—C16 | 1.477 (3) | C14—H14B | 0.980 |
N3—C14 | 1.490 (3) | C15—C16 | 1.517 (3) |
N3—C15 | 1.492 (3) | C15—H15A | 0.980 |
N3—H3A | 0.910 | C15—H15B | 0.980 |
N3—H3B | 0.910 | C16—H16A | 0.980 |
C1—C2 | 1.393 (3) | C16—H16B | 0.980 |
Cl4—Bi1—Cl3 | 92.375 (18) | F1—C6—C7 | 117.90 (16) |
Cl4—Bi1—Cl5 | 96.10 (2) | C8—C7—N2 | 123.26 (17) |
Cl3—Bi1—Cl5 | 97.124 (19) | C8—C7—C6 | 116.27 (17) |
Cl4—Bi1—Cl1 | 94.585 (16) | N2—C7—C6 | 120.35 (16) |
Cl3—Bi1—Cl1 | 93.506 (14) | C7—C8—C9 | 121.19 (17) |
Cl5—Bi1—Cl1 | 164.578 (16) | C7—C8—H8 | 119.4 |
Cl4—Bi1—Cl2 | 88.285 (17) | C9—C8—H8 | 119.4 |
Cl3—Bi1—Cl2 | 170.408 (16) | N1—C9—C8 | 120.56 (16) |
Cl5—Bi1—Cl2 | 92.318 (17) | N1—C9—C4 | 119.04 (16) |
Cl1—Bi1—Cl2 | 76.903 (12) | C8—C9—C4 | 120.39 (16) |
Cl4—Bi1—Cl2i | 169.401 (17) | N1—C10—C11 | 112.43 (16) |
Cl3—Bi1—Cl2i | 84.255 (16) | N1—C10—H10A | 109.1 |
Cl5—Bi1—Cl2i | 94.291 (17) | C11—C10—H10A | 109.1 |
Cl1—Bi1—Cl2i | 75.647 (12) | N1—C10—H10B | 109.1 |
Cl2—Bi1—Cl2i | 93.385 (16) | C11—C10—H10B | 109.1 |
Bi1—Cl1—Bi1i | 82.867 (18) | H10A—C10—H10B | 107.9 |
Bi1—Cl2—Bi1i | 79.513 (14) | C10—C11—H11A | 109.5 |
C12—O2—H2 | 109.5 | C10—C11—H11B | 109.5 |
C3—O3—H3 | 109.5 | H11A—C11—H11B | 109.5 |
H4A—O4—H4B | 110 (4) | C10—C11—H11C | 109.5 |
C1—N1—C9 | 120.76 (15) | H11A—C11—H11C | 109.5 |
C1—N1—C10 | 118.00 (15) | H11B—C11—H11C | 109.5 |
C9—N1—C10 | 121.24 (15) | O1—C12—O2 | 124.09 (19) |
C7—N2—C13 | 116.96 (15) | O1—C12—C2 | 121.17 (18) |
C7—N2—C16 | 116.57 (16) | O2—C12—C2 | 114.74 (17) |
C13—N2—C16 | 111.13 (16) | N2—C13—C14 | 110.36 (16) |
C14—N3—C15 | 110.96 (16) | N2—C13—H13A | 109.6 |
C14—N3—H3A | 109.4 | C14—C13—H13A | 109.6 |
C15—N3—H3A | 109.4 | N2—C13—H13B | 109.6 |
C14—N3—H3B | 109.4 | C14—C13—H13B | 109.6 |
C15—N3—H3B | 109.4 | H13A—C13—H13B | 108.1 |
H3A—N3—H3B | 108.0 | N3—C14—C13 | 110.88 (18) |
N1—C1—C2 | 122.72 (17) | N3—C14—H14A | 109.5 |
N1—C1—H1 | 118.6 | C13—C14—H14A | 109.5 |
C2—C1—H1 | 118.6 | N3—C14—H14B | 109.5 |
C1—C2—C3 | 119.14 (17) | C13—C14—H14B | 109.5 |
C1—C2—C12 | 121.21 (17) | H14A—C14—H14B | 108.1 |
C3—C2—C12 | 119.62 (16) | N3—C15—C16 | 110.00 (17) |
O3—C3—C2 | 123.19 (17) | N3—C15—H15A | 109.7 |
O3—C3—C4 | 118.21 (16) | C16—C15—H15A | 109.7 |
C2—C3—C4 | 118.61 (16) | N3—C15—H15B | 109.7 |
C5—C4—C9 | 118.83 (17) | C16—C15—H15B | 109.7 |
C5—C4—C3 | 121.43 (17) | H15A—C15—H15B | 108.2 |
C9—C4—C3 | 119.70 (16) | N2—C16—C15 | 110.71 (17) |
C6—C5—C4 | 119.41 (17) | N2—C16—H16A | 109.5 |
C6—C5—H5 | 120.3 | C15—C16—H16A | 109.5 |
C4—C5—H5 | 120.3 | N2—C16—H16B | 109.5 |
C5—C6—F1 | 118.21 (17) | C15—C16—H16B | 109.5 |
C5—C6—C7 | 123.80 (17) | H16A—C16—H16B | 108.1 |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1 | 0.83 | 1.85 | 2.583 (2) | 146 |
O2—H2···Cl6ii | 0.83 | 2.19 | 3.0150 (15) | 173 |
O4—H4A···Cl5 | 0.72 (2) | 2.56 (2) | 3.270 (2) | 170 (4) |
O4—H4B···Cl6 | 0.72 (2) | 2.47 (2) | 3.146 (2) | 157 (4) |
N3—H3A···Cl2iii | 0.91 | 2.51 | 3.3961 (19) | 165 |
N3—H3B···O4iv | 0.91 | 1.82 | 2.693 (3) | 160 |
Symmetry codes: (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | (C16H20FN3O3)2[Bi2Cl9]Cl·2H2O |
Mr | 1451.19 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 203 |
a, b, c (Å) | 13.9109 (12), 22.7104 (19), 14.5964 (12) |
β (°) | 92.798 (2) |
V (Å3) | 4605.8 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 8.27 |
Crystal size (mm) | 0.27 × 0.22 × 0.17 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector diffractometer |
Absorption correction | Gaussian (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.180, 0.334 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16736, 6987, 6081 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.735 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.061, 1.06 |
No. of reflections | 6987 |
No. of parameters | 282 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.58, −0.84 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2003), XP in SHELXTL (Sheldrick, 2008), publCIF (Version 1.9.0; Westrip, 2008).
Bi1—Bi1i | 3.7851 (3) | Bi1—Cl1 | 2.8599 (5) |
Bi1—Cl4 | 2.5471 (6) | Bi1—Cl2 | 2.9194 (6) |
Bi1—Cl3 | 2.5497 (5) | Bi1—Cl2i | 2.9984 (6) |
Bi1—Cl5 | 2.5781 (5) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1 | 0.83 | 1.85 | 2.583 (2) | 146 |
O2—H2···Cl6ii | 0.83 | 2.19 | 3.0150 (15) | 173 |
O4—H4A···Cl5 | 0.715 (18) | 2.563 (18) | 3.270 (2) | 170 (4) |
O4—H4B···Cl6 | 0.717 (19) | 2.47 (2) | 3.146 (2) | 157 (4) |
N3—H3A···Cl2iii | 0.91 | 2.51 | 3.3961 (19) | 165 |
N3—H3B···O4iv | 0.91 | 1.82 | 2.693 (3) | 160 |
Symmetry codes: (ii) x+1, y, z; (iii) x+1/2, y+1/2, z; (iv) x, −y+1, z+1/2. |
References
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (1998). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2003). SAINT (Version 6.45) and SADABS (Version 2.10). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
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.
Norfloxacin (nfH) belongs to the second-generation quinolone antimicrobial agents. According to a search of the Cambridge Structural Database (CSD, Version 5.28; Allen, 2002), well determined relevant structures are those where norfloxacin acts as an anion, a singly protonated cation or a zwitterion. The present research deals with the synthesis and structure of a chlorido-bismuth complex with the doubly protonated cation of norfloxacin (nfH3)2+.
The asymmetric unit of the title compound, (I), contains one Bi atom, five chlorine atoms, one nfH3 cation and one H2O molecule. The Bi atoms are coordinated by six Cl atoms in a distorted octahedral geometry. Two Bi-centred octahedra are linked by triple Cl bridges to form a dinuclear [Bi2Cl9]3- complex (Fig. 1), which lies on a twofold rotation axis, with a Bi···Bi distance of 3.7851 (3) Å. In the Bi-centred octahedra there are three short terminal Bi—Cl bonds [2.5471 (6)–2.5781 (5) Å] and three longer bridging bonds [2.8599 (5)–2.9984(6] Å). These anions pack in columns parallel to the [101] direction.
The protonation of nfH32+ is realised on the carbonyl atom O3 and N3 of the piperazine ring (Fig. 2). The hydrogen atom H3 is linked by an intramolecular hydrogen bond with O1 of the carboxyl group. O2 and N3 in the cation act as hydrogen-bond donors, via H2, H3A and H3B.
Water molecules, uncoordinated chloride anions (Cl6) and nfH32+ cations are linked in zigzag chains by hydrogen bonds parallel to the [102] direction (Fig. 3). In the chain, the nfH32+ cations are pairwise parallel (as a result of inversion symmetry), and there exist also π–π interactions between quinoline ring systems, with an interplanar distance of 3.27 (1) Å.
The combination of the hydrogen bonds and π–π stacking generates a three-dimensional network (Fig. 4).