Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100004340/fr1263sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100004340/fr1263Isup2.hkl |
CCDC reference: 147681
Pefloxacinium methanesulfonate was a gift from Rhone-Poulenc Rorer Pakistan (Pvt) Ltd, Wah Cant., Pakistan. It was recrystallized from dimethylformamide as colourless crystals, m.p. 543–544 K (dec.).
Towards the end of the refinement, a void area was indicated by the program PLATON (Spek, 1990) which was consistent with the position of the largest peak in the difference map suggesting water of solvation. O7 was included in the refinement initially allowing its site occupancy factor to refine in order to determine its % in the crystal. In the final round of calculations, O7 was included at 10% occupancy factor and refined isotropically ignoring H atoms attached to it. Distances used in H-atom calculations were C—H 0.93–0.97, N—H 0.91 and O—H 0.82 Å.
Data collection: Enraf-Nonius CAD-4 Software. Version 5.0. (Enraf-Nonius, 1989); cell refinement: Enraf-Nonius CAD-4 Software. Version 5.0. (Enraf-Nonius, 1989); data reduction: TEXSAN (Molecular Structure Corporation, 1994); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN (Molecular Structure Corporation, 1994); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) with the atomic numbering scheme and 30% ellipsoids. | |
Fig. 2. Packing diagram for (I) showing hydrogen bonds. |
C17H21FN3O3+·CH3SO3−·0.10H2O | Z = 2 |
Mr = 431.26 | F(000) = 454 |
Triclinic, P1 | Dx = 1.44 Mg m−3 |
a = 8.111 (3) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 10.013 (1) Å | Cell parameters from 25 reflections |
c = 13.277 (3) Å | θ = 10.0–25.0° |
α = 101.22 (1)° | µ = 1.91 mm−1 |
β = 102.85 (2)° | T = 293 K |
γ = 102.01 (1)° | Prismatic, colourless |
V = 994.9 (4) Å3 | 0.30 × 0.23 × 0.20 mm |
Enraf-Nonius CAD-4 diffractometer | 3167 reflections with I > 2.0σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.012 |
Graphite monochromator | θmax = 68.0°, θmin = 5.0° |
ω–2θ scans | h = 0→9 |
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968) | k = −12→11 |
Tmin = 0.60, Tmax = 0.70 | l = −15→15 |
3886 measured reflections | 3 standard reflections every 200 reflections |
3612 independent reflections | intensity decay: < 0.20% |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.4415P] where P = (Fo2 + 2Fc2)/3 |
3612 reflections | (Δ/σ)max < 0.001 |
266 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
C17H21FN3O3+·CH3SO3−·0.10H2O | γ = 102.01 (1)° |
Mr = 431.26 | V = 994.9 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.111 (3) Å | Cu Kα radiation |
b = 10.013 (1) Å | µ = 1.91 mm−1 |
c = 13.277 (3) Å | T = 293 K |
α = 101.22 (1)° | 0.30 × 0.23 × 0.20 mm |
β = 102.85 (2)° |
Enraf-Nonius CAD-4 diffractometer | 3167 reflections with I > 2.0σ(I) |
Absorption correction: empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968) | Rint = 0.012 |
Tmin = 0.60, Tmax = 0.70 | 3 standard reflections every 200 reflections |
3886 measured reflections | intensity decay: < 0.20% |
3612 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.35 e Å−3 |
3612 reflections | Δρmin = −0.41 e Å−3 |
266 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.77493 (6) | 0.29092 (5) | 0.99532 (4) | 0.03219 (15) | |
F1 | 0.65338 (19) | 0.75430 (13) | 0.57256 (10) | 0.0514 (3) | |
O1 | 0.9255 (2) | 0.1756 (2) | 0.26551 (12) | 0.0544 (4) | |
H1 | 0.8971 | 0.2501 | 0.2712 | 0.082* | |
O2 | 0.9419 (3) | 0.0148 (2) | 0.35648 (14) | 0.0682 (5) | |
O3 | 0.8243 (2) | 0.38882 (18) | 0.33421 (11) | 0.0485 (4) | |
O4 | 0.6665 (2) | 0.35098 (17) | 0.92482 (13) | 0.0478 (4) | |
O5 | 0.8995 (2) | 0.23530 (17) | 0.94905 (13) | 0.0483 (4) | |
O6 | 0.67168 (18) | 0.18731 (16) | 1.03640 (13) | 0.0438 (4) | |
N1 | 0.7871 (2) | 0.24239 (18) | 0.59762 (13) | 0.0365 (4) | |
N2 | 0.6446 (3) | 0.66246 (17) | 0.76079 (15) | 0.0437 (5) | |
N3 | 0.6690 (2) | 0.81227 (17) | 0.97290 (13) | 0.0340 (4) | |
H3 | 0.5601 | 0.8270 | 0.9597 | 0.041* | |
C1 | 0.8347 (3) | 0.1697 (2) | 0.51834 (16) | 0.0395 (5) | |
H1A | 0.8587 | 0.0843 | 0.5244 | 0.047* | |
C2 | 0.8500 (3) | 0.2140 (2) | 0.42876 (15) | 0.0383 (5) | |
C3 | 0.8139 (3) | 0.3442 (2) | 0.41591 (15) | 0.0359 (4) | |
C4 | 0.7670 (2) | 0.4239 (2) | 0.50284 (15) | 0.0325 (4) | |
C5 | 0.7348 (3) | 0.5560 (2) | 0.50046 (16) | 0.0360 (4) | |
H5 | 0.7426 | 0.5922 | 0.4418 | 0.043* | |
C6 | 0.6925 (3) | 0.6311 (2) | 0.58265 (16) | 0.0353 (4) | |
C7 | 0.6817 (2) | 0.5848 (2) | 0.67572 (15) | 0.0322 (4) | |
C8 | 0.7114 (3) | 0.4528 (2) | 0.67694 (15) | 0.0318 (4) | |
H8 | 0.7028 | 0.4170 | 0.7357 | 0.038* | |
C9 | 0.7535 (2) | 0.3730 (2) | 0.59286 (15) | 0.0311 (4) | |
C10 | 0.7612 (3) | 0.1787 (2) | 0.68610 (17) | 0.0459 (5) | |
H10A | 0.8079 | 0.2509 | 0.7530 | 0.055* | |
H10B | 0.8254 | 0.1074 | 0.6896 | 0.055* | |
C11 | 0.5707 (4) | 0.1127 (3) | 0.6721 (2) | 0.0652 (8) | |
H11A | 0.5056 | 0.1816 | 0.6640 | 0.098* | |
H11B | 0.5576 | 0.0794 | 0.7337 | 0.098* | |
H11C | 0.5271 | 0.0350 | 0.6097 | 0.098* | |
C12 | 0.9093 (3) | 0.1251 (3) | 0.34870 (17) | 0.0453 (5) | |
C13 | 0.6692 (3) | 0.8148 (2) | 0.78642 (18) | 0.0438 (5) | |
H13A | 0.5562 | 0.8357 | 0.7699 | 0.053* | |
H13B | 0.7376 | 0.8557 | 0.7433 | 0.053* | |
C14 | 0.7623 (3) | 0.8789 (2) | 0.90307 (18) | 0.0411 (5) | |
H14A | 0.8804 | 0.8674 | 0.9174 | 0.049* | |
H14B | 0.7707 | 0.9792 | 0.9198 | 0.049* | |
C15 | 0.6471 (3) | 0.6566 (2) | 0.94408 (16) | 0.0344 (4) | |
H15A | 0.5814 | 0.6126 | 0.9871 | 0.041* | |
H15B | 0.7612 | 0.6371 | 0.9583 | 0.041* | |
C16 | 0.5516 (3) | 0.5967 (2) | 0.82772 (16) | 0.0352 (4) | |
H16A | 0.5392 | 0.4958 | 0.8089 | 0.042* | |
H16B | 0.4351 | 0.6115 | 0.8149 | 0.042* | |
C17 | 0.7584 (3) | 0.8770 (3) | 1.08825 (18) | 0.0495 (6) | |
H17A | 0.6892 | 0.8371 | 1.1304 | 0.074* | |
H17B | 0.7722 | 0.9770 | 1.1033 | 0.074* | |
H17C | 0.8716 | 0.8586 | 1.1054 | 0.074* | |
C18 | 0.8987 (3) | 0.4291 (3) | 1.10682 (18) | 0.0532 (6) | |
H18A | 0.9763 | 0.3942 | 1.1547 | 0.080* | |
H18B | 0.8214 | 0.4663 | 1.1429 | 0.080* | |
H18C | 0.9660 | 0.5023 | 1.0840 | 0.080* | |
O7 | 0.221 (4) | 0.312 (3) | 0.717 (2) | 0.114 (9)* | 0.10 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0310 (2) | 0.0324 (3) | 0.0367 (3) | 0.01049 (19) | 0.01174 (19) | 0.01186 (19) |
F1 | 0.0725 (9) | 0.0412 (7) | 0.0514 (8) | 0.0250 (7) | 0.0207 (7) | 0.0221 (6) |
O1 | 0.0691 (11) | 0.0647 (11) | 0.0332 (8) | 0.0224 (9) | 0.0220 (8) | 0.0068 (8) |
O2 | 0.1002 (15) | 0.0716 (12) | 0.0494 (10) | 0.0499 (12) | 0.0310 (10) | 0.0119 (9) |
O3 | 0.0600 (10) | 0.0617 (10) | 0.0312 (8) | 0.0207 (8) | 0.0183 (7) | 0.0172 (7) |
O4 | 0.0517 (9) | 0.0466 (9) | 0.0502 (9) | 0.0224 (7) | 0.0084 (7) | 0.0203 (7) |
O5 | 0.0431 (8) | 0.0529 (9) | 0.0612 (10) | 0.0214 (7) | 0.0281 (8) | 0.0173 (8) |
O6 | 0.0344 (7) | 0.0419 (8) | 0.0640 (10) | 0.0103 (6) | 0.0209 (7) | 0.0253 (7) |
N1 | 0.0492 (10) | 0.0361 (9) | 0.0294 (8) | 0.0171 (8) | 0.0141 (7) | 0.0099 (7) |
N2 | 0.0669 (12) | 0.0253 (8) | 0.0463 (10) | 0.0101 (8) | 0.0316 (9) | 0.0094 (7) |
N3 | 0.0315 (8) | 0.0311 (8) | 0.0394 (9) | 0.0122 (7) | 0.0101 (7) | 0.0041 (7) |
C1 | 0.0470 (12) | 0.0389 (11) | 0.0338 (10) | 0.0164 (9) | 0.0115 (9) | 0.0057 (9) |
C2 | 0.0397 (11) | 0.0444 (12) | 0.0290 (10) | 0.0117 (9) | 0.0094 (8) | 0.0042 (9) |
C3 | 0.0332 (10) | 0.0448 (11) | 0.0275 (9) | 0.0081 (9) | 0.0061 (8) | 0.0085 (8) |
C4 | 0.0304 (9) | 0.0364 (10) | 0.0274 (9) | 0.0049 (8) | 0.0057 (8) | 0.0075 (8) |
C5 | 0.0356 (10) | 0.0404 (11) | 0.0318 (10) | 0.0069 (9) | 0.0072 (8) | 0.0145 (8) |
C6 | 0.0373 (10) | 0.0313 (10) | 0.0375 (11) | 0.0086 (8) | 0.0078 (8) | 0.0124 (8) |
C7 | 0.0321 (9) | 0.0302 (9) | 0.0316 (10) | 0.0046 (8) | 0.0083 (8) | 0.0062 (8) |
C8 | 0.0372 (10) | 0.0317 (10) | 0.0263 (9) | 0.0081 (8) | 0.0092 (8) | 0.0075 (8) |
C9 | 0.0318 (9) | 0.0317 (10) | 0.0277 (9) | 0.0068 (8) | 0.0059 (7) | 0.0065 (8) |
C10 | 0.0735 (16) | 0.0419 (12) | 0.0372 (11) | 0.0288 (11) | 0.0247 (11) | 0.0184 (9) |
C11 | 0.088 (2) | 0.0483 (14) | 0.0679 (17) | 0.0093 (14) | 0.0405 (16) | 0.0221 (13) |
C12 | 0.0470 (12) | 0.0556 (14) | 0.0320 (11) | 0.0184 (11) | 0.0103 (9) | 0.0032 (10) |
C13 | 0.0621 (14) | 0.0282 (10) | 0.0490 (13) | 0.0160 (10) | 0.0242 (11) | 0.0130 (9) |
C14 | 0.0448 (12) | 0.0258 (10) | 0.0553 (13) | 0.0089 (9) | 0.0219 (10) | 0.0076 (9) |
C15 | 0.0358 (10) | 0.0296 (10) | 0.0425 (11) | 0.0121 (8) | 0.0157 (9) | 0.0106 (8) |
C16 | 0.0387 (10) | 0.0288 (9) | 0.0405 (11) | 0.0065 (8) | 0.0188 (9) | 0.0077 (8) |
C17 | 0.0465 (13) | 0.0503 (13) | 0.0418 (12) | 0.0116 (11) | 0.0064 (10) | −0.0032 (10) |
C18 | 0.0531 (14) | 0.0589 (15) | 0.0382 (12) | −0.0075 (11) | 0.0171 (10) | 0.0089 (11) |
S1—O5 | 1.444 (2) | C5—H5 | 0.9300 |
S1—O4 | 1.444 (2) | C6—C7 | 1.415 (3) |
S1—O6 | 1.462 (2) | C7—C8 | 1.395 (3) |
S1—C18 | 1.754 (2) | C8—C9 | 1.392 (3) |
F1—C6 | 1.360 (2) | C8—H8 | 0.9300 |
O1—C12 | 1.322 (3) | C10—C11 | 1.503 (4) |
O1—H1 | 0.8200 | C10—H10A | 0.9700 |
O2—C12 | 1.206 (3) | C10—H10B | 0.9700 |
O3—C3 | 1.264 (2) | C11—H11A | 0.9600 |
N1—C1 | 1.336 (3) | C11—H11B | 0.9600 |
N1—C9 | 1.401 (3) | C11—H11C | 0.9600 |
N1—C10 | 1.475 (3) | C13—C14 | 1.507 (3) |
N2—C7 | 1.370 (3) | C13—H13A | 0.9700 |
N2—C16 | 1.453 (2) | C13—H13B | 0.9700 |
N2—C13 | 1.457 (3) | C14—H14A | 0.9700 |
N3—C17 | 1.488 (3) | C14—H14B | 0.9700 |
N3—C14 | 1.490 (3) | C15—C16 | 1.504 (3) |
N3—C15 | 1.494 (2) | C15—H15A | 0.9700 |
N3—H3 | 0.9100 | C15—H15B | 0.9700 |
C1—C2 | 1.369 (3) | C16—H16A | 0.9700 |
C1—H1A | 0.9300 | C16—H16B | 0.9700 |
C2—C3 | 1.427 (3) | C17—H17A | 0.9600 |
C2—C12 | 1.480 (3) | C17—H17B | 0.9600 |
C3—C4 | 1.442 (3) | C17—H17C | 0.9600 |
C4—C9 | 1.404 (3) | C18—H18A | 0.9600 |
C4—C5 | 1.406 (3) | C18—H18B | 0.9600 |
C5—C6 | 1.352 (3) | C18—H18C | 0.9600 |
O5—S1—O4 | 113.06 (10) | N1—C10—H10B | 109.3 |
O5—S1—O6 | 111.81 (9) | C11—C10—H10B | 109.3 |
O4—S1—O6 | 112.36 (10) | H10A—C10—H10B | 108.0 |
O5—S1—C18 | 106.28 (12) | C10—C11—H11A | 109.5 |
O4—S1—C18 | 106.79 (12) | C10—C11—H11B | 109.5 |
O6—S1—C18 | 105.95 (11) | H11A—C11—H11B | 109.5 |
C12—O1—H1 | 109.5 | C10—C11—H11C | 109.5 |
C1—N1—C9 | 120.01 (17) | H11A—C11—H11C | 109.5 |
C1—N1—C10 | 118.77 (17) | H11B—C11—H11C | 109.5 |
C9—N1—C10 | 121.13 (16) | O2—C12—O1 | 121.0 (2) |
C7—N2—C16 | 122.13 (16) | O2—C12—C2 | 124.1 (2) |
C7—N2—C13 | 125.47 (17) | O1—C12—C2 | 114.9 (2) |
C16—N2—C13 | 111.88 (16) | N2—C13—C14 | 110.33 (18) |
C17—N3—C14 | 111.99 (17) | N2—C13—H13A | 109.6 |
C17—N3—C15 | 111.94 (17) | C14—C13—H13A | 109.6 |
C14—N3—C15 | 109.78 (15) | N2—C13—H13B | 109.6 |
C17—N3—H3 | 107.6 | C14—C13—H13B | 109.6 |
C14—N3—H3 | 107.6 | H13A—C13—H13B | 108.1 |
C15—N3—H3 | 107.6 | N3—C14—C13 | 111.74 (17) |
N1—C1—C2 | 123.7 (2) | N3—C14—H14A | 109.3 |
N1—C1—H1A | 118.2 | C13—C14—H14A | 109.3 |
C2—C1—H1A | 118.2 | N3—C14—H14B | 109.3 |
C1—C2—C3 | 120.14 (19) | C13—C14—H14B | 109.3 |
C1—C2—C12 | 118.0 (2) | H14A—C14—H14B | 107.9 |
C3—C2—C12 | 121.86 (19) | N3—C15—C16 | 109.51 (16) |
O3—C3—C2 | 122.54 (19) | N3—C15—H15A | 109.8 |
O3—C3—C4 | 121.47 (19) | C16—C15—H15A | 109.8 |
C2—C3—C4 | 115.99 (18) | N3—C15—H15B | 109.8 |
C9—C4—C5 | 117.89 (18) | C16—C15—H15B | 109.8 |
C9—C4—C3 | 121.24 (18) | H15A—C15—H15B | 108.2 |
C5—C4—C3 | 120.87 (18) | N2—C16—C15 | 111.29 (17) |
C6—C5—C4 | 120.66 (18) | N2—C16—H16A | 109.4 |
C6—C5—H5 | 119.7 | C15—C16—H16A | 109.4 |
C4—C5—H5 | 119.7 | N2—C16—H16B | 109.4 |
C5—C6—F1 | 117.59 (18) | C15—C16—H16B | 109.4 |
C5—C6—C7 | 123.09 (19) | H16A—C16—H16B | 108.0 |
F1—C6—C7 | 119.28 (18) | N3—C17—H17A | 109.5 |
N2—C7—C8 | 120.68 (18) | N3—C17—H17B | 109.5 |
N2—C7—C6 | 123.39 (18) | H17A—C17—H17B | 109.5 |
C8—C7—C6 | 115.94 (18) | N3—C17—H17C | 109.5 |
C9—C8—C7 | 122.00 (18) | H17A—C17—H17C | 109.5 |
C9—C8—H8 | 119.0 | H17B—C17—H17C | 109.5 |
C7—C8—H8 | 119.0 | S1—C18—H18A | 109.5 |
C8—C9—N1 | 120.67 (17) | S1—C18—H18B | 109.5 |
C8—C9—C4 | 120.39 (18) | H18A—C18—H18B | 109.5 |
N1—C9—C4 | 118.92 (17) | S1—C18—H18C | 109.5 |
N1—C10—C11 | 111.6 (2) | H18A—C18—H18C | 109.5 |
N1—C10—H10A | 109.3 | H18B—C18—H18C | 109.5 |
C11—C10—H10A | 109.3 | ||
C9—N1—C1—C2 | −1.4 (3) | C7—C8—C9—N1 | 178.33 (18) |
C10—N1—C1—C2 | 175.1 (2) | C7—C8—C9—C4 | −0.2 (3) |
N1—C1—C2—C3 | −0.2 (3) | C1—N1—C9—C8 | −177.15 (19) |
N1—C1—C2—C12 | 178.1 (2) | C10—N1—C9—C8 | 6.4 (3) |
C1—C2—C3—O3 | −179.2 (2) | C1—N1—C9—C4 | 1.4 (3) |
C12—C2—C3—O3 | 2.5 (3) | C10—N1—C9—C4 | −175.06 (19) |
C1—C2—C3—C4 | 1.7 (3) | C5—C4—C9—C8 | −0.7 (3) |
C12—C2—C3—C4 | −176.58 (19) | C3—C4—C9—C8 | 178.72 (18) |
O3—C3—C4—C9 | 179.21 (19) | C5—C4—C9—N1 | −179.24 (17) |
C2—C3—C4—C9 | −1.7 (3) | C3—C4—C9—N1 | 0.2 (3) |
O3—C3—C4—C5 | −1.4 (3) | C1—N1—C10—C11 | −98.8 (2) |
C2—C3—C4—C5 | 177.73 (18) | C9—N1—C10—C11 | 77.6 (3) |
C9—C4—C5—C6 | 0.1 (3) | C1—C2—C12—O2 | 1.4 (4) |
C3—C4—C5—C6 | −179.34 (19) | C3—C2—C12—O2 | 179.7 (2) |
C4—C5—C6—F1 | −176.39 (17) | C1—C2—C12—O1 | −178.4 (2) |
C4—C5—C6—C7 | 1.4 (3) | C3—C2—C12—O1 | −0.1 (3) |
C16—N2—C7—C8 | −31.1 (3) | C7—N2—C13—C14 | −132.3 (2) |
C13—N2—C7—C8 | 157.9 (2) | C16—N2—C13—C14 | 55.9 (3) |
C16—N2—C7—C6 | 148.9 (2) | C17—N3—C14—C13 | −178.93 (17) |
C13—N2—C7—C6 | −22.1 (3) | C15—N3—C14—C13 | 56.1 (2) |
C5—C6—C7—N2 | 177.8 (2) | N2—C13—C14—N3 | −55.2 (2) |
F1—C6—C7—N2 | −4.4 (3) | C17—N3—C15—C16 | 178.34 (16) |
C5—C6—C7—C8 | −2.2 (3) | C14—N3—C15—C16 | −56.6 (2) |
F1—C6—C7—C8 | 175.57 (17) | C7—N2—C16—C15 | 129.6 (2) |
N2—C7—C8—C9 | −178.43 (19) | C13—N2—C16—C15 | −58.3 (2) |
C6—C7—C8—C9 | 1.6 (3) | N3—C15—C16—N2 | 58.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O6i | 0.91 | 1.87 | 2.739 (2) | 159 |
O1—H1···O3 | 0.82 | 1.76 | 2.523 (2) | 155 |
Symmetry code: (i) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C17H21FN3O3+·CH3SO3−·0.10H2O |
Mr | 431.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.111 (3), 10.013 (1), 13.277 (3) |
α, β, γ (°) | 101.22 (1), 102.85 (2), 102.01 (1) |
V (Å3) | 994.9 (4) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 1.91 |
Crystal size (mm) | 0.30 × 0.23 × 0.20 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | Empirical (using intensity measurements) ψ-scan (3 reflections) (North et al., 1968) |
Tmin, Tmax | 0.60, 0.70 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 3886, 3612, 3167 |
Rint | 0.012 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.111, 1.10 |
No. of reflections | 3612 |
No. of parameters | 266 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.41 |
Computer programs: Enraf-Nonius CAD-4 Software. Version 5.0. (Enraf-Nonius, 1989), TEXSAN (Molecular Structure Corporation, 1994), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997).
S1—O5 | 1.444 (2) | N1—C9 | 1.401 (3) |
S1—O4 | 1.444 (2) | N1—C10 | 1.475 (3) |
S1—O6 | 1.462 (2) | N2—C7 | 1.370 (3) |
S1—C18 | 1.754 (2) | N2—C16 | 1.453 (2) |
F1—C6 | 1.360 (2) | N2—C13 | 1.457 (3) |
O1—C12 | 1.322 (3) | N3—C17 | 1.488 (3) |
O2—C12 | 1.206 (3) | N3—C14 | 1.490 (3) |
O3—C3 | 1.264 (2) | N3—C15 | 1.494 (2) |
N1—C1 | 1.336 (3) | ||
O5—S1—O4 | 113.06 (10) | C9—N1—C10 | 121.13 (16) |
O5—S1—O6 | 111.81 (9) | C7—N2—C16 | 122.13 (16) |
O4—S1—O6 | 112.36 (10) | C7—N2—C13 | 125.47 (17) |
O5—S1—C18 | 106.28 (12) | C16—N2—C13 | 111.88 (16) |
O4—S1—C18 | 106.79 (12) | C17—N3—C14 | 111.99 (17) |
O6—S1—C18 | 105.95 (11) | C17—N3—C15 | 111.94 (17) |
C1—N1—C9 | 120.01 (17) | C14—N3—C15 | 109.78 (15) |
C1—N1—C10 | 118.77 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O6i | 0.91 | 1.87 | 2.739 (2) | 159 |
O1—H1···O3 | 0.82 | 1.76 | 2.523 (2) | 155 |
Symmetry code: (i) −x+1, −y+1, −z+2. |
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Pefloxacin belongs to the second generation quinolone antimicrobial agents. These antimicrobials exert their action by inhibiting enzyme DNA-gyrase which is responsible for the continuous introduction of negative supercoils into DNA (Alfred et al., 1996). Pefloxacin gives satisfactory clinical responses in the treatment of respiratory tract infections including gram negative bacillary, staphylococcal pneumonia (Lauwers et al., 1986), gram negative pneumonia (Giamarellou et al., 1987) and chronic bronchitis (Maesens et al., 1987). It is also used in the treatment of prostatitis (Guibert et al., 1990), neisseria, gonorrhea (Ridgway, 1993) and possesses excellent activity against several gram negative meningeal pathogens (Scheld & Sande, 1983). It may cause headache, dizziness, insomnia, rashes, gastrointestinal symptoms like nausea, vomiting, diarrhea (John & Hooper, 1989). The crystal structures of pefloxacinium methanesulfonate dihydrate (Toffoli et al., 1987), silver pefloxacin hexahydrate (Baenziger et al., 1986) and dipefloxacinium tetrachloro platinum(II) dihydrate (Toffoli et al., 1988) have already been reported. In this article, we report the crystal and molecular structure of pefloxacinium methanesulfonate 0.10 hydrate, (I). \sch
The asymmetric unit of (I) contains a pefloxacinium cation, a methanesulfonate anion and a partially occupied water of solvation with 0.10 site occupancy factor (Fig. 1). The cation is composed of an essentially planar quinoline ring system [maximum deviation 0.029 (2) Å] which is substituted with ethyl, fluoro, oxo, carboxyl and methylpiperazinium groups. The bond distances and bond angles in the pefloxacinium ion are in excellent agreement with the corresponding dimensions reported in the structures of pefloxacinium methanesulfonate dihydrate (Toffoli et al., 1987), silver pefloxacin hexahydrate (Baenziger et al., 1986) and dipefloxacinium tetrachloro platinum(II) dihydrate (Toffoli et al., 1988); the mean values being: Csp3—N (ammonium N3) 1.491 (2), Csp3—N 1.462 (10), Csp2—N 1.37 (3), Csp3—Csp3 1.505 (2) and C—Caromatic 1.39 (2) Å. The carboxyl group in (I) lies in the plane of the quinolyl moiety [angle between the two planes being 3.3 (3)°] while the plane of the N1,C10,C11 atoms is inclined at 80.5 (1)° to the quinolyl moiety. The six-membered piperazinyl ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.566 (2) Å, θ = 177.3 (2) and ϕ = 60 (6)°. The methanesulfonate anion also exhibits normal molecular dimensions with a mean S═O distance of 1.450 (8) with the longest distance associated with the O6 atom involved in a hydrogen bond [1.462 (2) Å].
The structure is stabilized by hydrogen bonds involving the terminal piperazinyl N atom of the pefloxacinium and an O atom of the methanesulfonate ions with strong N—H···O interactions [N3···O6 2.739 (2) Å and N3—H3···O6 159°]. The carbonyl and carboxyl groups are also involved in a strong intramolecular hydrogen bond O—H···O [O···O 2.523 (2) Å and O1—H1···O3 155°]. The pefloxacinium ions in (I) lie parallel to each other about inversion centers with N-ethyl groups oriented inwards (Fig. 2), similar to the packing observed in dipefloxacinium tetrachloro platinum(II) dihydrate (Toffoli et al., 1988). In the structures of pefloxacinium methanesulfonate dihydrate (Toffoli et al., 1987), and silver pefloxacin hexahydrate (Baenziger et al., 1986), the pefloxacinium moieties lie parallel to each other in a head-to-tail manner with the N-ethyl groups oriented in the opposite directions. The `outwards' motif is also present in (I). The separation o fthe quinoline rings in the `inwards' and `outwards' motifs in (I) is 3.35 and 3.34 Å, respectively.
The atom O7 of the partially occupied water of solvation lies at distances between 3.13 (3) to 3.38 (3) Å from O2, O3, C16 and N1 atoms. There is a short intramolecular contact H8···H16A, 2.01 Å which does not seem to influence the geometry about the atoms in the close proximity of these atoms.
The crystal structures of the quinolones related to (I) which have been reported include: an adduct of magnesium sulfate with ciprofloxacin (Turel et al., 1996), norfloxacin 2DCl·D2O (Wallis et al., 1994), and iron(III) complex of ciprofloxacin (Wallis et al., 1995).