ACCESSION: MSBNK-Athens_Univ-AU283703
RECORD_TITLE: Clobetasol propionate; LC-ESI-QTOF; MS2; CE: 30 eV; R=35000; [M+H]+
DATE: 2019.05.31
AUTHORS: Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2019 Department of Chemistry, University of Athens
COMMENT: CONFIDENCE standard compound
COMMENT: INTERNAL_ID 2837
CH$NAME: Clobetasol propionate
CH$NAME: [(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C25H32ClFO5
CH$EXACT_MASS: 466.1922300
CH$SMILES: CCC(=O)O[C@@]1([C@@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)C(=O)CCl
CH$IUPAC: InChI=1S/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1
CH$LINK: CAS
25122-41-2
CH$LINK: CHEBI
31414
CH$LINK: KEGG
D01272
CH$LINK: PUBCHEM
CID:32798
CH$LINK: INCHIKEY
CBGUOGMQLZIXBE-XGQKBEPLSA-N
CH$LINK: CHEMSPIDER
30399
CH$LINK: COMPTOX
DTXSID6045907
AC$INSTRUMENT: Bruker maXis Impact
AC$INSTRUMENT_TYPE: LC-ESI-QTOF
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE CID
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 30 eV
AC$MASS_SPECTROMETRY: RESOLUTION 35000
AC$CHROMATOGRAPHY: COLUMN_NAME Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
AC$CHROMATOGRAPHY: FLOW_GRADIENT 99/1 at 0-1 min, 61/39 at 3 min, 0.1/99.9 at 14-16 min, 99/1 at 16.1-20 min
AC$CHROMATOGRAPHY: FLOW_RATE 200 uL/min at 0-3 min, 400 uL/min at 14 min, 480 uL/min at 16-19 min, 200 uL/min at 19.1-20 min
AC$CHROMATOGRAPHY: RETENTION_TIME 10.664 min
AC$CHROMATOGRAPHY: SOLVENT A 90:10 water:methanol with 0.01% formic acid and 5mM ammonium formate
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.01% formic acid and 5mM ammonium formate
MS$FOCUSED_ION: BASE_PEAK 313.216
MS$FOCUSED_ION: PRECURSOR_M/Z 467.1995
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: RECALIBRATE identity on assigned fragments and MS1
MS$DATA_PROCESSING: WHOLE RMassBank 2.10.1
PK$SPLASH: splash10-004i-0692000000-7d9c3b657519d3e36c53
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
119.0848 ClFH17O3+ 4 119.0845 2.38
121.0637 C8H9O+ 3 121.0648 -9.34
121.1004 C9H13+ 4 121.1012 -6.48
122.0678 C7[13]CH9O+ 1 122.0687 -7.65
122.1048 C8[13]CH13+ 1 122.1051 -2.15
123.0794 C8H11O+ 3 123.0804 -8.35
128.0617 C10H8+ 4 128.0621 -2.8
129.0684 CH15ClFO3+ 4 129.0688 -2.96
131.0483 ClFH13O4+ 4 131.0481 1.24
131.0841 CH17ClFO3+ 4 131.0845 -2.88
132.056 ClFH14O4+ 4 132.0559 0.39
133.0405 C6H10ClO+ 2 133.0415 -6.93
133.063 C3H14ClO3+ 4 133.0626 2.7
133.1 C10H13+ 4 133.1012 -9.08
134.1044 C9[13]CH13+ 1 134.1051 -4.95
135.0793 C9H11O+ 4 135.0804 -8.48
136.0832 C8[13]CH11O+ 1 136.0843 -8.69
137.0953 ClFH19O4+ 4 137.095 2.03
141.0692 C2H15ClFO3+ 4 141.0688 2.87
143.0245 C7H8ClO+ 2 143.0258 -9.26
143.061 C8H12Cl+ 2 143.0622 -8.58
143.0844 C2H17ClFO3+ 4 143.0845 -0.31
144.0578 C7H9FO2+ 4 144.0581 -1.95
144.0889 C5H17ClO2+ 2 144.0912 -15.93
145.0634 CH15ClFO4+ 4 145.0637 -2.5
145.0998 C2H19ClFO3+ 4 145.1001 -2.56
146.0685 C4H15ClO3+ 2 146.0704 -13.41
147.0793 C10H11O+ 4 147.0804 -8.06
148.0824 C9[13]CH11O+ 1 148.0843 -13.41
149.0947 C10H13O+ 4 149.0961 -9.32
150.0987 C9[13]CH13O+ 1 150.1 -8.72
153.046 C9H10Cl+ 2 153.0466 -3.82
155.0603 C9H12Cl+ 2 155.0622 -12.13
155.0842 C3H17ClFO3+ 4 155.0845 -1.63
156.0904 C6H17ClO2+ 3 156.0912 -4.7
157.0407 C8H10ClO+ 2 157.0415 -5.1
157.0636 C2H15ClFO4+ 4 157.0637 -0.65
157.0771 C9H14Cl+ 2 157.0779 -4.7
157.0999 C12H13+ 4 157.1012 -7.93
158.0715 C2H16ClFO4+ 4 158.0716 -0.33
158.1032 C11[13]CH13+ 1 158.1051 -11.72
159.0791 C11H11O+ 4 159.0804 -8.51
160.0832 C10[13]CH11O+ 1 160.0843 -7.07
161.0588 CH15ClFO5+ 4 161.0587 0.74
161.0951 C11H13O+ 4 161.0961 -6.06
162.0978 C10[13]CH13O+ 1 162.1 -13.64
163.0743 C4H16ClO4+ 4 163.0732 6.67
165.0701 C4H16[37]ClO4+ 1 165.0708 -4.21
167.0609 C10H12Cl+ 2 167.0622 -7.87
168.063 C9[13]CH12Cl+ 1 168.0661 -18.39
169.0408 C9H10ClO+ 3 169.0415 -3.83
169.06 C10H12[37]Cl+ 1 169.0598 1.21
169.0753 C10H14Cl+ 2 169.0779 -15.13
169.1009 C13H13+ 4 169.1012 -1.91
171.0556 C9H12ClO+ 2 171.0571 -8.73
171.0792 C6H16ClO3+ 4 171.0782 5.45
171.1156 C4H21ClFO3+ 4 171.1158 -1.18
172.0602 C8[13]CH12ClO+ 1 172.061 -4.71
172.0828 C5[13]CH16ClO3+ 1 172.0822 3.69
173.0534 C9H12[37]ClO+ 1 173.0547 -7.52
173.0949 C12H13O+ 4 173.0961 -6.83
174.0981 C11[13]CH13O+ 1 174.1 -10.85
175.0742 C2H17ClFO5+ 4 175.0743 -0.4
175.0918 C12H12F+ 3 175.0918 0.38
175.11 C6H20ClO3+ 4 175.1095 2.79
177.0901 C5H18ClO4+ 4 177.0888 7.31
179.0603 C11H12Cl+ 2 179.0622 -10.72
179.085 C5H18[37]ClO4+ 1 179.0864 -7.71
179.1064 C11H15O2+ 4 179.1067 -1.31
181.0396 C10H10ClO+ 2 181.0415 -10.5
183.0561 C10H12ClO+ 3 183.0571 -5.55
183.0795 C4H17ClFO4+ 4 183.0794 0.76
183.1147 C8H20ClO2+ 4 183.1146 0.35
184.0874 C4H18ClFO4+ 4 184.0872 0.87
185.0715 C10H14ClO+ 3 185.0728 -6.71
185.095 C13H13O+ 4 185.0961 -5.95
186.0749 C9[13]CH14ClO+ 1 186.0767 -9.49
186.0982 C12[13]CH13O+ 1 186.1 -9.56
187.0735 C12H11O2+ 4 187.0754 -9.77
187.1108 C13H15O+ 4 187.1117 -5.26
188.0773 C11[13]CH11O2+ 1 188.0793 -10.21
188.1129 C12[13]CH15O+ 1 188.1156 -14.75
189.0696 C15H9+ 4 189.0699 -1.72
189.0902 C6H18ClO4+ 4 189.0888 7.15
190.0934 C10H16ClF+ 3 190.0919 7.78
191.0855 C6H18[37]ClO4+ 1 191.0864 -4.91
193.0763 C12H14Cl+ 2 193.0779 -8.2
193.0982 C9H18ClO2+ 4 193.099 -4.29
194.0792 C11[13]CH14Cl+ 1 194.0818 -13.2
195.0553 C11H12ClO+ 2 195.0571 -9.19
195.0763 C12H14[37]Cl+ 1 195.0755 4.22
195.1157 C6H21ClFO3+ 4 195.1158 -0.58
196.0604 C10[13]CH12ClO+ 1 196.061 -3.09
197.0336 C10H10ClO2+ 2 197.0364 -13.98
197.056 C11H12[37]ClO+ 1 197.0547 6.51
197.0714 C11H14ClO+ 3 197.0728 -7.14
197.095 C14H13O+ 4 197.0961 -5.55
198.0998 C13[13]CH13O+ 1 198.1 -0.79
199.0741 C4H17ClFO5+ 4 199.0743 -0.99
199.1104 C8H20ClO3+ 4 199.1095 4.46
200.1143 C7[13]CH20ClO3+ 1 200.1135 4.14
201.0887 C7H18ClO4+ 5 201.0888 -0.32
201.1268 C5H23ClFO4+ 4 201.1263 2.03
203.068 C6H16ClO5+ 4 203.0681 -0.57
203.1056 C7H20ClO4+ 4 203.1045 5.66
204.1084 C11H18ClF+ 3 204.1076 3.96
205.1016 C7H20[37]ClO4+ 1 205.1021 -2.29
207.0793 C6H17ClFO4+ 4 207.0794 -0.3
207.1174 C13H16FO+ 4 207.118 -2.71
208.0855 C9H17ClO3+ 4 208.0861 -2.89
209.0723 C12H14ClO+ 3 209.0728 -2.15
209.0952 C6H19ClFO4+ 4 209.095 0.78
210.1019 C9H19ClO3+ 4 210.1017 1.01
211.0741 C5H17ClFO5+ 4 211.0743 -0.9
211.111 C15H15O+ 4 211.1117 -3.48
212.1152 C14[13]CH15O+ 1 212.1156 -1.97
213.0661 C11H14ClO2+ 4 213.0677 -7.57
213.0873 C8H18ClO4+ 5 213.0888 -7.02
213.1262 C9H22ClO3+ 4 213.1252 4.9
214.1294 C8[13]CH22ClO3+ 1 214.1291 1.3
215.0646 C11H14[37]ClO2+ 1 215.0653 -3.09
215.1078 C11H16FO3+ 4 215.1078 -0.03
219.0564 C13H12ClO+ 3 219.0571 -3.5
221.0722 C13H14ClO+ 3 221.0728 -2.71
221.095 C7H19ClFO4+ 4 221.095 -0.24
221.1315 C8H23ClFO3+ 4 221.1314 0.4
222.101 C10H19ClO3+ 4 222.1017 -3.08
223.1105 C16H15O+ 4 223.1117 -5.48
224.1153 C15[13]CH15O+ 1 224.1156 -1.65
225.0899 C6H19ClFO5+ 4 225.09 -0.17
225.1251 C13H18FO2+ 4 225.1285 -15.42
226.1337 C12[13]CH18FO2+ 1 226.1324 5.7
227.1056 C6H21ClFO5+ 4 227.1056 0.17
227.1426 C16H19O+ 4 227.143 -1.81
230.1086 C18H14+ 4 230.109 -1.68
231.1156 C9H21ClFO3+ 4 231.1158 -0.97
233.0708 C14H14ClO+ 3 233.0728 -8.43
233.095 C8H19ClFO4+ 4 233.095 -0.13
234.1027 C8H20ClFO4+ 4 234.1029 -0.71
235.1106 C8H21ClFO4+ 4 235.1107 -0.25
235.1479 C18H19+ 4 235.1481 -0.82
236.1167 C11H21ClO3+ 4 236.1174 -2.9
236.151 C17[13]CH19+ 1 236.152 -4.25
237.0928 C13H14FO3+ 4 237.0921 2.63
237.1255 C17H17O+ 4 237.1274 -7.97
238.1315 C16[13]CH17O+ 1 238.1313 0.92
239.1059 C7H21ClFO5+ 4 239.1056 1.03
239.1418 C17H19O+ 4 239.143 -5.38
240.1114 C10H21ClO4+ 5 240.1123 -3.81
240.1466 C16[13]CH19O+ 1 240.1469 -1.37
241.122 C16H17O2+ 4 241.1223 -1.22
241.1586 C14H22FO2+ 4 241.1598 -5.12
242.1244 C15[13]CH17O2+ 1 242.1262 -7.61
242.1641 C13[13]CH22FO2+ 1 242.1637 1.64
243.1143 C13H20ClO2+ 4 243.1146 -1.31
244.1221 C13H21ClO2+ 4 244.1225 -1.3
245.0951 C9H19ClFO4+ 4 245.095 0.21
245.1319 C19H17+ 4 245.1325 -2.42
246.1032 C9H20ClFO4+ 4 246.1029 1.16
246.1391 C18[13]CH17+ 1 246.1364 11.15
247.0516 C14H12ClO2+ 4 247.052 -1.74
247.0867 C15H16ClO+ 3 247.0884 -6.9
247.1094 C12H20ClO3+ 4 247.1095 -0.44
248.1183 C9H22ClFO4+ 4 248.1185 -0.74
249.0829 C15H16[37]ClO+ 1 249.086 -12.39
249.1262 C18H17O+ 4 249.1274 -4.59
249.1623 C10H27ClFO3+ 4 249.1627 -1.56
250.1326 C17[13]CH17O+ 1 250.1313 5.32
250.1699 C13H27ClO2+ 4 250.1694 1.93
251.0816 C14H16ClO2+ 4 251.0833 -7.01
251.1051 C8H21ClFO5+ 5 251.1056 -2.06
251.1411 C12H24ClO3+ 4 251.1408 1.02
252.1481 C12H25ClO3+ 4 252.1487 -2.08
253.1575 C18H21O+ 4 253.1587 -4.71
254.1615 C17[13]CH21O+ 1 254.1626 -4.46
257.0707 C16H14ClO+ 3 257.0728 -8.07
257.1303 C14H22ClO2+ 4 257.1303 -0.02
258.1409 C17H19FO+ 5 258.1414 -1.99
259.0687 C16H13ClF+ 3 259.0684 0.95
259.1097 C13H20ClO3+ 4 259.1095 0.61
259.1474 C11H25ClFO3+ 4 259.1471 1.09
260.1173 C13H21ClO3+ 4 260.1174 -0.14
260.1552 C11H26ClFO3+ 4 260.1549 1.23
261.0667 C15H14ClO2+ 4 261.0677 -3.82
261.1257 C13H22ClO3+ 4 261.1252 1.88
261.1632 C17H22FO+ 5 261.1649 -6.73
262.1341 C10H24ClFO4+ 4 262.1342 -0.23
262.1692 C16[13]CH22FO+ 1 262.1688 1.39
263.1422 C19H19O+ 4 263.143 -3.19
264.112 C12H21ClO4+ 5 264.1123 -1.1
264.146 C18[13]CH19O+ 1 264.1469 -3.58
265.1536 C17[13]C2H19O+ 1 265.1503 12.54
266.1638 C13H27ClO3+ 4 266.1643 -2.06
267.0957 C15H17ClFO+ 4 267.0946 3.81
267.1369 C18H19O2+ 5 267.138 -3.96
267.1729 C19H23O+ 4 267.1743 -5.44
268.1397 C17[13]CH19O2+ 1 268.1419 -8.09
268.1762 C18[13]CH23O+ 1 268.1782 -7.68
271.0868 C17H16ClO+ 3 271.0884 -6.1
271.1102 C11H21ClFO4+ 4 271.1107 -1.75
272.1181 C11H22ClFO4+ 4 272.1185 -1.59
273.1262 C11H23ClFO4+ 4 273.1263 -0.59
273.1618 C15H26ClO2+ 4 273.1616 0.65
274.1325 C14H23ClO3+ 4 274.133 -1.98
275.0821 C16H16ClO2+ 4 275.0833 -4.56
275.1425 C20H19O+ 4 275.143 -1.89
276.1486 C14H25ClO3+ 4 276.1487 -0.25
277.1217 C10H23ClFO5+ 5 277.1213 1.64
277.1575 C11H27ClFO4+ 4 277.1576 -0.34
278.1658 C11H28ClFO4+ 4 278.1655 1.12
279.1726 C20H23O+ 4 279.1743 -6.08
280.1762 C19[13]CH23O+ 1 280.1782 -7.13
281.1521 C13H26ClO4+ 5 281.1514 2.51
281.1847 C18[13]C2H23O+ 1 281.1816 11.01
282.1557 C12[13]CH26ClO4+ 1 282.1553 1.28
283.1477 C13H26[37]ClO4+ 1 283.149 -4.58
284.1548 C13H26ClFO3+ 5 284.1549 -0.2
285.0706 C20H10FO+ 5 285.071 -1.62
285.1047 C15H19ClFO2+ 3 285.1052 -1.71
286.1342 C21H18O+ 4 286.1352 -3.44
287.1188 C18H20ClO+ 3 287.1197 -3.05
287.132 C20[13]CH18O+ 1 287.1391 -24.87
288.1211 C17[13]CH20ClO+ 1 288.1236 -8.9
288.1497 C21H20O+ 4 288.1509 -4.03
289.1143 C18H19ClF+ 3 289.1154 -3.62
289.1554 C20[13]CH20O+ 1 289.1548 2.09
290.1274 C14H23ClO4+ 5 290.1279 -1.99
291.1365 C17H20FO3+ 5 291.1391 -9.08
291.1738 C18H24FO2+ 4 291.1755 -5.81
292.1441 C16[13]CH20FO3+ 1 292.143 3.72
292.1774 C17[13]CH24FO2+ 1 292.1794 -6.9
293.1491 C14H26ClO4+ 5 293.1514 -7.95
293.1859 C16[13]C2H24FO2+ 1 293.1827 10.93
295.0892 C16H17ClFO2+ 4 295.0896 -1.16
295.1278 C17H21ClFO+ 5 295.1259 6.12
295.1684 C11H29ClFO5+ 5 295.1682 0.71
296.1756 C11H30ClFO5+ 5 296.176 -1.4
297.1043 C19H18ClO+ 3 297.1041 0.62
297.1812 C18H27ClF+ 5 297.178 10.97
298.177 C17[13]CH27ClF+ 1 298.1819 -16.38
299.0831 C18H16ClO2+ 4 299.0833 -0.85
301.1579 C22H21O+ 4 301.1587 -2.66
302.1623 C21[13]CH21O+ 1 302.1626 -0.82
303.1643 C20[13]C2H21O+ 1 303.1659 -5.34
304.1442 C12H26ClFO5+ 5 304.1447 -1.59
305.1523 C12H27ClFO5+ 5 305.1526 -0.91
306.1614 C21H22O2+ 5 306.1614 0.04
307.1652 C20[13]CH22O2+ 1 307.1653 -0.31
309.14 C21H22Cl+ 3 309.1405 -1.57
309.184 C21H25O2+ 5 309.1849 -2.89
310.1888 C20[13]CH25O2+ 1 310.1888 0.04
311.1177 C20H20ClO+ 3 311.1197 -6.57
312.1227 C20H21ClO+ 3 312.1275 -15.54
313.0988 C16H19ClFO3+ 4 313.1001 -4.31
313.1354 C20H22ClO+ 3 313.1354 0.14
314.1041 C15[13]CH19ClFO3+ 1 314.104 0.17
314.135 C19[13]CH22ClO+ 1 314.1393 -13.75
315.0979 C16H19[37]ClFO3+ 1 315.0977 0.61
315.132 C20H22[37]ClO+ 1 315.133 -3.21
319.1682 C16H28ClO4+ 5 319.1671 3.7
320.1714 C15[13]CH28ClO4+ 1 320.171 1.38
321.1691 C18H25O5+ 5 321.1697 -1.73
322.112 C21H19ClO+ 4 322.1119 0.3
324.1728 C18H25FO4+ 4 324.1731 -1
327.1507 C21H24ClO+ 3 327.151 -1
328.1546 C20[13]CH24ClO+ 1 328.1549 -1.13
329.1468 C21H24[37]ClO+ 1 329.1486 -5.38
330.1494 C19H22O5+ 3 330.1462 9.83
337.1339 C22H22ClO+ 3 337.1354 -4.36
337.1791 C22H25O3+ 5 337.1798 -2.28
338.1391 C21[13]CH22ClO+ 1 338.1393 -0.41
339.1335 C22H22[37]ClO+ 1 339.133 1.59
340.1335 C20H20O5+ 3 340.1305 8.74
345.1614 C21H26ClO2+ 4 345.1616 -0.49
346.1672 C20[13]CH26ClO2+ 1 346.1655 4.89
347.1575 C21H26[37]ClO2+ 1 347.1592 -4.95
355.1455 C22H24ClO2+ 4 355.1459 -1.33
356.1488 C21[13]CH24ClO2+ 1 356.1498 -3.05
357.1424 C22H24[37]ClO2+ 1 357.1435 -3.14
358.1457 C25H23Cl+ 3 358.1483 -7.09
373.1559 C22H26ClO3+ 3 373.1565 -1.61
374.1582 C21[13]CH26ClO3+ 1 374.1604 -5.83
375.1514 C22H26[37]ClO3+ 1 375.1541 -7.2
376.1562 C25H25ClO+ 3 376.1588 -6.95
PK$NUM_PEAK: 284
PK$PEAK: m/z int. rel.int.
119.0848 3884 35
121.0637 10860 98
121.1004 7488 67
122.0678 1272 11
122.1048 736 6
123.0794 860 7
128.0617 1404 12
129.0684 960 8
131.0483 564 5
131.0841 3968 35
132.056 1008 9
133.0405 2412 21
133.063 2028 18
133.1 5480 49
134.1044 860 7
135.0793 13592 123
136.0832 1408 12
137.0953 1168 10
141.0692 1096 9
143.0245 1244 11
143.061 2384 21
143.0844 2704 24
144.0578 756 6
144.0889 712 6
145.0634 4976 45
145.0998 2588 23
146.0685 868 7
147.0793 55308 501
148.0824 5088 46
149.0947 4248 38
150.0987 800 7
153.046 664 6
155.0603 752 6
155.0842 1004 9
156.0904 616 5
157.0407 680 6
157.0636 880 7
157.0771 2524 22
157.0999 2856 25
158.0715 1476 13
158.1032 564 5
159.0791 21608 195
160.0832 2804 25
161.0588 2360 21
161.0951 14524 131
162.0978 2200 19
163.0743 1820 16
165.0701 844 7
167.0609 7592 68
168.063 648 5
169.0408 1372 12
169.06 2872 26
169.0753 2072 18
169.1009 712 6
171.0556 15816 143
171.0792 38680 350
171.1156 3120 28
172.0602 1504 13
172.0828 4184 37
173.0534 5592 50
173.0949 23620 214
174.0981 2920 26
175.0742 1020 9
175.0918 1372 12
175.11 1772 16
177.0901 2116 19
179.0603 552 5
179.085 712 6
179.1064 684 6
181.0396 600 5
183.0561 4152 37
183.0795 2060 18
183.1147 912 8
184.0874 804 7
185.0715 27912 253
185.095 25924 235
186.0749 2640 23
186.0982 3528 31
187.0735 29916 271
187.1108 3392 30
188.0773 3528 31
188.1129 748 6
189.0696 796 7
189.0902 3376 30
190.0934 568 5
191.0855 1424 12
193.0763 4512 40
193.0982 712 6
194.0792 996 9
195.0553 3316 30
195.0763 1432 12
195.1157 844 7
196.0604 568 5
197.0336 684 6
197.056 848 7
197.0714 2296 20
197.095 6388 57
198.0998 1468 13
199.0741 3812 34
199.1104 5804 52
200.1143 636 5
201.0887 1160 10
201.1268 1040 9
203.068 1404 12
203.1056 3476 31
204.1084 672 6
205.1016 1240 11
207.0793 552 5
207.1174 900 8
208.0855 1676 15
209.0723 984 8
209.0952 5200 47
210.1019 2156 19
211.0741 940 8
211.111 9208 83
212.1152 2072 18
213.0661 2416 21
213.0873 1520 13
213.1262 25168 228
214.1294 3388 30
215.0646 1240 11
215.1078 1144 10
219.0564 760 6
221.0722 632 5
221.095 7268 65
221.1315 644 5
222.101 3168 28
223.1105 18620 168
224.1153 5360 48
225.0899 860 7
225.1251 3264 29
226.1337 596 5
227.1056 1284 11
227.1426 2524 22
230.1086 600 5
231.1156 1348 12
233.0708 1192 10
233.095 844 7
234.1027 3000 27
235.1106 6392 57
235.1479 2292 20
236.1167 2392 21
236.151 640 5
237.0928 684 6
237.1255 6456 58
238.1315 1176 10
239.1059 1720 15
239.1418 7372 66
240.1114 556 5
240.1466 1268 11
241.122 3612 32
241.1586 3324 30
242.1244 724 6
242.1641 680 6
243.1143 820 7
244.1221 572 5
245.0951 564 5
245.1319 2512 22
246.1032 1032 9
246.1391 784 7
247.0516 1188 10
247.0867 1824 16
247.1094 1148 10
248.1183 6172 55
249.0829 812 7
249.1262 7820 70
249.1623 888 8
250.1326 2368 21
250.1699 1252 11
251.0816 1332 12
251.1051 880 7
251.1411 4596 41
252.1481 2280 20
253.1575 22744 206
254.1615 4248 38
257.0707 1036 9
257.1303 932 8
258.1409 744 6
259.0687 744 6
259.1097 1488 13
259.1474 1464 13
260.1173 3052 27
260.1552 1440 13
261.0667 1100 9
261.1257 3448 31
261.1632 4776 43
262.1341 4084 37
262.1692 1348 12
263.1422 76084 690
264.112 972 8
264.146 15820 143
265.1536 1520 13
266.1638 780 7
267.0957 608 5
267.1369 2524 22
267.1729 2968 26
268.1397 716 6
268.1762 736 6
271.0868 1216 11
271.1102 1068 9
272.1181 1044 9
273.1262 4484 40
273.1618 2084 18
274.1325 2244 20
275.0821 1720 15
275.1425 9340 84
276.1486 5912 53
277.1217 2472 22
277.1575 30024 272
278.1658 110140 999
279.1726 65020 589
280.1762 12248 111
281.1521 4316 39
281.1847 1636 14
282.1557 556 5
283.1477 1388 12
284.1548 660 5
285.0706 596 5
285.1047 1136 10
286.1342 5084 46
287.1188 1904 17
287.132 1616 14
288.1211 640 5
288.1497 12140 110
289.1143 1104 10
289.1554 3332 30
290.1274 1028 9
291.1365 2500 22
291.1738 26744 242
292.1441 624 5
292.1774 5720 51
293.1491 676 6
293.1859 564 5
295.0892 992 8
295.1278 704 6
295.1684 2368 21
296.1756 6612 59
297.1043 736 6
297.1812 2940 26
298.177 692 6
299.0831 1104 10
301.1579 27856 252
302.1623 7356 66
303.1643 804 7
304.1442 1552 14
305.1523 776 7
306.1614 13276 120
307.1652 2992 27
309.14 740 6
309.184 4580 41
310.1888 1204 10
311.1177 1564 14
312.1227 748 6
313.0988 3084 27
313.1354 5936 53
314.1041 828 7
314.135 1604 14
315.0979 828 7
315.132 1976 17
319.1682 13892 126
320.1714 2672 24
321.1691 872 7
322.112 980 8
324.1728 1376 12
327.1507 16736 151
328.1546 3612 32
329.1468 5296 48
330.1494 1004 9
337.1339 13792 125
337.1791 2124 19
338.1391 3168 28
339.1335 4548 41
340.1335 968 8
345.1614 3372 30
346.1672 1056 9
347.1575 1472 13
355.1455 34920 316
356.1488 9044 82
357.1424 10796 97
358.1457 1564 14
373.1559 6188 56
374.1582 1296 11
375.1514 1808 16
376.1562 696 6
//
