ACCESSION: MSBNK-Eawag-EQ367853
RECORD_TITLE: Doxycycline; LC-ESI-QFT; MS2; CE: 45; R=35000; [M-H]-
DATE: 2015.08.26
AUTHORS: Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag and Thomaidis N, University of Athens
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2015 Eawag, Duebendorf, Switzerland
COMMENT: CONFIDENCE standard compound
COMMENT: EAWAG_UCHEM_ID 3678
CH$NAME: Doxycycline
CH$NAME: 8-carbamoyl-10-(dimethylazaniumyl)-4,6a,7,11-tetrahydroxy-12-methyl-6,9-dioxo-10a,11,11a,12-tetrahydro-10H-tetracen-5-olate
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C22H24N2O8
CH$EXACT_MASS: 444.15327
CH$SMILES: CC1C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
CH$IUPAC: InChI=1S/C22H24N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29/h4-7,10,14-15,17,25-27,30,32H,1-3H3,(H2,23,31)
CH$LINK: CAS
564-25-0
CH$LINK: PUBCHEM
CID:54681536
CH$LINK: INCHIKEY
SGKRLCUYIXIAHR-UHFFFAOYSA-N
CH$LINK: CHEMSPIDER
10482106
AC$INSTRUMENT: Q Exactive Plus Orbitrap Thermo Scientific
AC$INSTRUMENT_TYPE: LC-ESI-QFT
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE NEGATIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE HCD
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 45 (nominal)
AC$MASS_SPECTROMETRY: RESOLUTION 35000
AC$CHROMATOGRAPHY: COLUMN_NAME XBridge C18 3.5um, 2.1x50mm, Waters
AC$CHROMATOGRAPHY: FLOW_GRADIENT 90/10 at 0 min, 50/50 at 4 min, 5/95 at 17 min, 5/95 at 25 min, 90/10 at 25.1 min, 90/10 at 30 min
AC$CHROMATOGRAPHY: FLOW_RATE 200 ul/min
AC$CHROMATOGRAPHY: RETENTION_TIME 6.3 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 443.1457
MS$FOCUSED_ION: PRECURSOR_M/Z 443.146
MS$FOCUSED_ION: PRECURSOR_TYPE [M-H]-
MS$DATA_PROCESSING: RECALIBRATE loess on assigned fragments and MS1
MS$DATA_PROCESSING: REANALYZE Peaks with additional N2/O included
MS$DATA_PROCESSING: WHOLE RMassBank 1.9.6
PK$SPLASH: splash10-0a4i-0591000000-9a17ac193dace0d396f7
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
58.0298 C2H4NO- 1 58.0298 -0.82
63.024 C5H3- 1 63.024 -0.69
65.0032 C4HO- 1 65.0033 -1.05
65.0396 C5H5- 1 65.0397 -0.98
65.9986 C3NO- 1 65.9985 0.35
67.0189 C4H3O- 1 67.0189 -0.27
68.0141 C3H2NO- 1 68.0142 -0.84
68.9983 C3HO2- 1 68.9982 0.97
69.0346 C4H5O- 1 69.0346 0.75
71.0139 C3H3O2- 1 71.0139 0.38
72.9933 C2HO3- 1 72.9931 1.95
79.0189 C5H3O- 1 79.0189 -0.86
80.0266 C5H4O- 1 80.0268 -2.54
81.0346 C5H5O- 1 81.0346 0.02
83.0139 C4H3O2- 1 83.0139 0.33
83.0503 C5H7O- 1 83.0502 1.22
84.009 C3H2NO2- 1 84.0091 -0.86
85.0295 C4H5O2- 1 85.0295 0.44
86.0247 C3H4NO2- 1 86.0248 -0.14
91.019 C6H3O- 1 91.0189 0.24
93.0345 C6H5O- 1 93.0346 -0.63
94.0299 C5H4NO- 1 94.0298 0.88
95.0138 C5H3O2- 1 95.0139 -0.14
96.009 C4H2NO2- 1 96.0091 -0.64
96.0217 C5H4O2- 1 96.0217 0.13
96.0455 C5H6NO- 1 96.0455 0.13
96.993 C4HO3- 1 96.9931 -0.8
97.0294 C5H5O2- 1 97.0295 -0.96
99.0088 C4H3O3- 1 99.0088 0.02
100.0768 C5H10NO- 1 100.0768 -0.27
102.056 C4H8NO2- 1 102.0561 -0.22
107.0138 C6H3O2- 1 107.0139 -0.59
107.0503 C7H7O- 1 107.0502 0.11
108.0217 C6H4O2- 1 108.0217 -0.17
109.0295 C6H5O2- 1 109.0295 -0.21
110.0611 C6H8NO- 1 110.0611 -0.34
111.0087 C5H3O3- 1 111.0088 -0.7
112.0405 C5H6NO2- 1 112.0404 0.61
112.0768 C6H10NO- 1 112.0768 0.02
117.0345 C8H5O- 1 117.0346 -0.5
119.0138 C7H3O2- 1 119.0139 -0.28
119.0502 C8H7O- 1 119.0502 -0.15
120.0218 C7H4O2- 1 120.0217 0.93
121.0293 C7H5O2- 1 121.0295 -1.26
121.0533 C7H7NO- 1 121.0533 0.23
121.0659 C8H9O- 1 121.0659 -0.15
122.0373 C7H6O2- 1 122.0373 -0.23
123.0088 C6H3O3- 1 123.0088 0.02
124.0165 C6H4O3- 1 124.0166 -0.59
124.0404 C6H6NO2- 1 124.0404 -0.18
124.0769 C7H10NO- 1 124.0768 0.83
124.9881 C5HO4- 1 124.988 0.22
125.0244 C6H5O3- 1 125.0244 0.18
125.072 C6H9N2O- 1 125.072 -0.29
126.0195 C5H4NO3- 1 126.0197 -1.32
126.0561 C6H8NO2- 1 126.0561 0.06
134.0248 C7H4NO2- 1 134.0248 0.36
135.0088 C7H3O3- 1 135.0088 0.31
135.0453 C8H7O2- 1 135.0452 0.72
136.0166 C7H4O3- 1 136.0166 -0.17
136.0403 C7H6NO2- 1 136.0404 -0.97
136.0767 C8H10NO- 1 136.0768 -0.5
136.988 C6HO4- 1 136.988 -0.53
137.0244 C7H5O3- 1 137.0244 -0.27
137.0481 C7H7NO2- 1 137.0482 -0.64
138.0195 C6H4NO3- 1 138.0197 -1.06
138.0323 C7H6O3- 1 138.0322 0.27
138.056 C7H8NO2- 1 138.0561 -0.38
138.0925 C8H12NO- 1 138.0924 0.38
139.015 C5H3N2O3- 1 139.0149 0.54
139.0274 C6H5NO3- 1 139.0275 -0.8
140.0355 C6H6NO3- 1 140.0353 1.02
140.0718 C7H10NO2- 1 140.0717 0.48
141.0193 C6H5O4- 1 141.0193 -0.3
141.0667 C6H9N2O2- 1 141.067 -1.78
142.0145 C5H4NO4- 1 142.0146 -0.43
142.9985 C5H3O5- 1 142.9986 -0.4
143.0826 C6H11N2O2- 1 143.0826 0.2
146.0374 C9H6O2- 1 146.0373 0.7
147.0451 C9H7O2- 1 147.0452 -0.29
149.0121 C7H3NO3- 1 149.0118 1.6
149.0237 C8H5O3- 1 149.0244 -4.82
149.0481 C8H7NO2- 1 149.0482 -0.79
149.0607 C9H9O2- 1 149.0608 -0.69
150.0197 C7H4NO3- 1 150.0197 0.22
151.0038 C7H3O4- 1 151.0037 0.52
151.0276 C7H5NO3- 1 151.0275 0.92
152.0115 C7H4O4- 1 152.0115 -0.11
152.0353 C7H6NO3- 1 152.0353 0.09
152.0717 C8H10NO2- 1 152.0717 0.05
153.0196 C7H5O4- 1 153.0193 1.42
153.0434 C7H7NO3- 1 153.0431 1.69
154.0384 C6H6N2O3- 1 154.0384 0.26
154.0874 C8H12NO2- 1 154.0874 0.05
157.0659 C11H9O- 1 157.0659 0.39
158.0371 C10H6O2- 1 158.0373 -1.44
159.0451 C10H7O2- 1 159.0452 -0.33
159.0815 C11H11O- 1 159.0815 -0.18
161.0245 C9H5O3- 1 161.0244 0.64
161.0608 C10H9O2- 1 161.0608 0.23
162.0197 C8H4NO3- 1 162.0197 -0.04
163.0038 C8H3O4- 1 163.0037 0.48
163.0275 C8H5NO3- 1 163.0275 0.11
163.0765 C10H11O2- 1 163.0765 0.47
164.0117 C8H4O4- 1 164.0115 0.99
164.0355 C8H6NO3- 1 164.0353 1.36
164.0592 C8H8N2O2- 1 164.0591 0.21
164.0717 C9H10NO2- 1 164.0717 0.17
165.0193 C8H5O4- 1 165.0193 -0.13
165.0432 C8H7NO3- 1 165.0431 0.11
166.0146 C7H4NO4- 1 166.0146 0.17
166.0511 C8H8NO3- 1 166.051 0.5
167.0224 C7H5NO4- 1 167.0224 -0.04
167.0463 C7H7N2O3- 1 167.0462 0.27
168.0303 C7H6NO4- 1 168.0302 0.23
168.0666 C8H10NO3- 1 168.0666 -0.04
169.0142 C7H5O5- 1 169.0142 -0.22
169.0254 C6H5N2O4- 1 169.0255 -0.24
169.0616 C7H9N2O3- 1 169.0619 -1.69
171.0454 C11H7O2- 1 171.0452 1.5
171.0818 C12H11O- 1 171.0815 1.53
172.0529 C11H8O2- 1 172.053 -0.22
173.0607 C11H9O2- 1 173.0608 -0.48
174.0323 C10H6O3- 1 174.0322 0.5
175.0403 C10H7O3- 1 175.0401 1.33
175.0765 C11H11O2- 1 175.0765 0.04
177.0304 C8H5N2O3- 1 177.0306 -0.88
177.0669 C9H9N2O2- 1 177.067 -0.12
178.0145 C8H4NO4- 1 178.0146 -0.51
178.0508 C9H8NO3- 1 178.051 -0.82
178.9987 C8H3O5- 1 178.9986 0.58
179.0826 C9H11N2O2- 1 179.0826 0.22
180.0302 C8H6NO4- 1 180.0302 -0.23
180.0666 C9H10NO3- 1 180.0666 -0.2
181.0382 C8H7NO4- 1 181.0381 0.9
181.0614 C8H9N2O3- 1 181.0619 -2.35
182.0821 C9H12NO3- 1 182.0823 -0.92
185.0607 C12H9O2- 1 185.0608 -0.45
186.0688 C12H10O2- 1 186.0686 0.82
187.04 C11H7O3- 1 187.0401 -0.52
187.0764 C12H11O2- 1 187.0765 -0.39
188.048 C11H8O3- 1 188.0479 0.41
189.0563 C11H9O3- 1 189.0557 2.92
189.067 C10H9N2O2- 1 189.067 0.26
189.0921 C12H13O2- 1 189.0921 -0.28
192.0542 C9H8N2O3- 1 192.054 0.83
194.0735 C14H10O- 1 194.0737 -0.95
195.041 C8H7N2O4- 1 195.0411 -0.57
195.0775 C9H11N2O3- 1 195.0775 0.02
196.0252 C8H6NO5- 1 196.0251 0.33
196.0531 C13H8O2- 1 196.053 0.47
196.0616 C9H10NO4- 1 196.0615 0.3
197.0608 C13H9O2- 1 197.0608 -0.27
197.0927 C9H13N2O3- 1 197.0932 -2.41
198.0771 C9H12NO4- 1 198.0772 -0.66
199.0399 C12H7O3- 1 199.0401 -1.04
199.0764 C13H11O2- 1 199.0765 -0.17
200.0482 C12H8O3- 1 200.0479 1.34
201.0558 C12H9O3- 1 201.0557 0.61
201.0924 C13H13O2- 1 201.0921 1.53
203.0715 C12H11O3- 1 203.0714 0.45
204.0422 C11H8O4- 1 204.0428 -2.83
207.0774 C10H11N2O3- 1 207.0775 -0.66
208.0611 C10H10NO4- 1 208.0615 -2.27
209.0608 C14H9O2- 1 209.0608 -0.11
210.0687 C14H10O2- 1 210.0686 0.15
211.0403 C13H7O3- 1 211.0401 1.2
211.0765 C14H11O2- 1 211.0765 0.22
212.0479 C13H8O3- 1 212.0479 0.27
213.0556 C13H9O3- 1 213.0557 -0.46
213.0919 C14H13O2- 1 213.0921 -1.14
214.0273 C12H6O4- 1 214.0272 0.53
214.0638 C13H10O3- 1 214.0635 1.01
215.0346 C12H7O4- 1 215.035 -1.87
215.0714 C13H11O3- 1 215.0714 0.1
217.0506 C12H9O4- 1 217.0506 0.08
218.0588 C12H10O4- 1 218.0585 1.75
219.0813 C16H11O- 1 219.0815 -1
221.0614 C15H9O2- 1 221.0608 2.47
221.0974 C16H13O- 1 221.0972 0.82
222.0686 C15H10O2- 1 222.0686 -0.08
223.0767 C15H11O2- 1 223.0765 0.88
224.048 C14H8O3- 1 224.0479 0.3
224.0843 C15H12O2- 1 224.0843 0.23
225.056 C14H9O3- 1 225.0557 1.3
225.0922 C15H13O2- 1 225.0921 0.39
226.0635 C14H10O3- 1 226.0635 -0.19
226.0728 C10H12NO5- 1 226.0721 3.16
226.0875 C14H12NO2- 1 226.0874 0.65
227.0351 C13H7O4- 1 227.035 0.47
227.0714 C14H11O3- 1 227.0714 -0.03
229.0506 C13H9O4- 1 229.0506 -0.18
229.087 C14H13O3- 1 229.087 0.05
231.0665 C13H11O4- 1 231.0663 0.86
232.0523 C16H8O2- 1 232.053 -2.79
233.0607 C16H9O2- 1 233.0608 -0.36
234.0686 C16H10O2- 1 234.0686 0.05
235.0765 C16H11O2- 1 235.0765 0.07
236.0472 C15H8O3- 1 236.0479 -2.77
237.056 C15H9O3- 1 237.0557 1.32
237.0921 C16H13O2- 1 237.0921 -0.01
238.0635 C15H10O3- 1 238.0635 -0.01
238.0874 C15H12NO2- 1 238.0874 0.28
239.0714 C15H11O3- 1 239.0714 0.22
240.0429 C14H8O4- 1 240.0428 0.34
241.0509 C14H9O4- 1 241.0506 1.19
241.0871 C15H13O3- 1 241.087 0.13
243.1026 C15H15O3- 1 243.1027 -0.4
244.0377 C13H8O5- 1 244.0377 -0.17
247.0762 C17H11O2- 1 247.0765 -1.11
248.0479 C16H8O3- 1 248.0479 -0.09
248.0719 C16H10NO2- 1 248.0717 0.68
248.0839 C17H12O2- 1 248.0843 -1.73
249.0554 C16H9O3- 1 249.0557 -1.12
249.0918 C17H13O2- 1 249.0921 -1.1
250.0635 C16H10O3- 1 250.0635 -0.01
251.0713 C16H11O3- 1 251.0714 -0.15
252.0427 C15H8O4- 1 252.0428 -0.58
252.0669 C15H10NO3- 1 252.0666 1
252.0792 C16H12O3- 1 252.0792 -0.05
252.103 C16H14NO2- 1 252.103 -0.01
253.0515 C15H9O4- 1 253.0506 3.39
253.0869 C16H13O3- 1 253.087 -0.39
254.0583 C15H10O4- 1 254.0585 -0.5
255.0664 C15H11O4- 1 255.0663 0.46
256.0979 C15H14NO3- 1 256.0979 0.01
256.1343 C16H18NO2- 1 256.1343 -0.01
257.0459 C14H9O5- 1 257.0455 1.33
257.0817 C15H13O4- 1 257.0819 -0.94
258.1139 C15H16NO3- 1 258.1136 1.25
258.15 C16H20NO2- 1 258.15 0.15
260.0475 C17H8O3- 1 260.0479 -1.47
261.0555 C17H9O3- 1 261.0557 -1.03
262.0873 C17H12NO2- 1 262.0874 -0.05
263.0712 C17H11O3- 1 263.0714 -0.52
264.0428 C16H8O4- 1 264.0428 -0.1
264.0787 C17H12O3- 1 264.0792 -1.87
264.1029 C17H14NO2- 1 264.103 -0.5
265.0502 C16H9O4- 1 265.0506 -1.63
265.087 C17H13O3- 1 265.087 -0.18
266.0584 C16H10O4- 1 266.0585 -0.18
266.0952 C17H14O3- 1 266.0948 1.27
267.0663 C16H11O4- 1 267.0663 0.22
267.1029 C17H15O3- 1 267.1027 0.87
268.0741 C16H12O4- 1 268.0741 -0.03
268.0979 C16H14NO3- 1 268.0979 0.05
268.1345 C17H18NO2- 1 268.1343 0.92
269.0819 C16H13O4- 1 269.0819 -0.08
270.1132 C16H16NO3- 1 270.1136 -1.51
270.1491 C17H20NO2- 1 270.15 -3.01
271.0616 C15H11O5- 1 271.0612 1.52
271.0976 C16H15O4- 1 271.0976 0.03
273.0769 C15H13O5- 1 273.0768 0.19
275.0715 C18H11O3- 1 275.0714 0.37
276.0427 C17H8O4- 1 276.0428 -0.42
276.0653 C17H10NO3- 2 276.0666 -4.84
276.0795 C18H12O3- 1 276.0792 1.22
276.1036 C18H14NO2- 1 276.103 2.2
277.0505 C17H9O4- 1 277.0506 -0.44
277.0867 C18H13O3- 1 277.087 -1.15
277.1104 C18H15NO2- 1 277.1108 -1.4
278.0585 C17H10O4- 1 278.0585 0.05
278.0823 C17H12NO3- 1 278.0823 0.26
278.1188 C18H16NO2- 1 278.1187 0.42
279.0661 C17H11O4- 1 279.0663 -0.55
280.0379 C16H8O5- 1 280.0377 0.74
280.0745 C17H12O4- 1 280.0741 1.37
280.0978 C17H14NO3- 1 280.0979 -0.49
281.082 C17H13O4- 1 281.0819 0.24
281.1053 C17H15NO3- 1 281.1057 -1.54
282.0533 C16H10O5- 1 282.0534 -0.22
282.0765 C16H12NO4- 1 282.0772 -2.52
282.1135 C17H16NO3- 1 282.1136 -0.38
283.097 C17H15O4- 1 283.0976 -2.02
284.1291 C17H18NO3- 1 284.1292 -0.55
285.0768 C16H13O5- 1 285.0768 -0.34
286.1445 C17H20NO3- 1 286.1449 -1.39
288.067 C18H10NO3- 1 288.0666 1.16
290.0222 C17H6O5- 1 290.0221 0.27
290.0822 C18H12NO3- 1 290.0823 -0.2
291.0664 C18H11O4- 1 291.0663 0.4
292.037 C17H8O5- 1 292.0377 -2.44
292.0746 C18H12O4- 1 292.0741 1.62
292.0976 C18H14NO3- 1 292.0979 -1.12
292.1341 C19H18NO2- 1 292.1343 -0.62
293.0459 C17H9O5- 1 293.0455 1.17
293.0821 C18H13O4- 1 293.0819 0.61
294.0537 C17H10O5- 1 294.0534 1.01
294.0899 C18H14O4- 1 294.0898 0.59
294.1142 C18H16NO3- 1 294.1136 2.12
294.1499 C19H20NO2- 1 294.15 -0.01
295.061 C17H11O5- 1 295.0612 -0.8
295.0977 C18H15O4- 1 295.0976 0.33
296.093 C17H14NO4- 1 296.0928 0.5
296.1292 C18H18NO3- 1 296.1292 -0.06
297.0768 C17H13O5- 1 297.0768 -0.16
300.1244 C17H18NO4- 1 300.1241 1.03
304.0372 C18H8O5- 1 304.0377 -1.85
304.0614 C18H10NO4- 1 304.0615 -0.37
304.0976 C19H14NO3- 1 304.0979 -1.11
305.0454 C18H9O5- 1 305.0455 -0.48
305.1051 C19H15NO3- 1 305.1057 -2.04
306.0761 C18H12NO4- 1 306.0772 -3.44
307.0612 C18H11O5- 1 307.0612 -0.09
308.093 C18H14NO4- 1 308.0928 0.64
308.1294 C19H18NO3- 1 308.1292 0.72
309.0767 C18H13O5- 1 309.0768 -0.57
310.145 C19H20NO3- 1 310.1449 0.53
311.0928 C18H15O5- 1 311.0925 1.13
312.1242 C18H18NO4- 1 312.1241 0.28
313.0722 C17H13O6- 1 313.0718 1.56
314.1395 C18H20NO4- 1 314.1398 -0.96
318.0772 C19H12NO4- 1 318.0772 0.12
318.1138 C20H16NO3- 1 318.1136 0.67
319.0621 C19H11O5- 1 319.0612 2.89
320.0695 C19H12O5- 1 320.069 1.4
320.1285 C20H18NO3- 1 320.1292 -2.36
321.0629 C18H11NO5- 2 321.0643 -4.15
321.1008 C19H15NO4- 1 321.1007 0.29
322.0485 C18H10O6- 1 322.0483 0.57
322.1093 C19H16NO4- 1 322.1085 2.54
323.1178 C19H17NO4- 2 323.1163 4.75
324.0874 C18H14NO5- 1 324.0877 -0.94
326.1037 C18H16NO5- 1 326.1034 1.05
326.1396 C19H20NO4- 1 326.1398 -0.65
328.156 C19H22NO4- 1 328.1554 1.7
334.072 C19H12NO5- 1 334.0721 -0.29
335.0555 C19H11O6- 1 335.0561 -1.86
335.1397 C20H19N2O3- 1 335.1401 -1.36
336.0874 C19H14NO5- 1 336.0877 -1.09
336.1241 C20H18NO4- 1 336.1241 -0.09
337.0722 C19H13O6- 1 337.0718 1.27
337.095 C19H15NO5- 1 337.0956 -1.58
338.0799 C19H14O6- 1 338.0796 0.78
338.1401 C20H20NO4- 1 338.1398 0.91
340.1191 C19H18NO5- 1 340.119 0.31
349.0963 C20H15NO5- 1 349.0956 2.23
353.1509 C20H21N2O4- 1 353.1507 0.51
354.1349 C20H20NO5- 1 354.1347 0.49
356.1501 C20H22NO5- 1 356.1503 -0.64
358.1297 C19H20NO6- 1 358.1296 0.19
362.068 C20H12NO6- 1 362.067 2.65
363.0506 C20H11O7- 1 363.051 -1.17
364.1194 C21H18NO5- 1 364.119 0.86
371.1619 C20H23N2O5- 1 371.1612 1.84
382.1298 C21H20NO6- 1 382.1296 0.47
400.1405 C21H22NO7- 1 400.1402 0.76
408.1088 C22H18NO7- 1 408.1089 -0.18
PK$NUM_PEAK: 348
PK$PEAK: m/z int. rel.int.
58.0298 1907.9 1
63.024 3057.9 2
65.0032 2088.9 1
65.0396 2509.9 1
65.9986 15520.8 10
67.0189 2613 1
68.0141 1567.5 1
68.9983 14743.9 9
69.0346 6150.1 4
71.0139 6453.3 4
72.9933 1891.5 1
79.0189 2774.3 1
80.0266 2012.1 1
81.0346 6213.7 4
83.0139 10277.2 6
83.0503 1788.5 1
84.009 46254.8 31
85.0295 6161.4 4
86.0247 5461.2 3
91.019 2142.4 1
93.0345 17531.7 11
94.0299 1581.9 1
95.0138 115104 78
96.009 9569 6
96.0217 2832.2 1
96.0455 1753.4 1
96.993 25263.8 17
97.0294 23044.9 15
99.0088 19761 13
100.0768 13146.2 8
102.056 1756 1
107.0138 11842.4 8
107.0503 5641.6 3
108.0217 25154 17
109.0295 126815.9 85
110.0611 7668.9 5
111.0087 15550.7 10
112.0405 7794.1 5
112.0768 2725.5 1
117.0345 2663.8 1
119.0138 69170.7 46
119.0502 36946 25
120.0218 7560.6 5
121.0293 4731.4 3
121.0533 2192.2 1
121.0659 25079.5 17
122.0373 2049.5 1
123.0088 64522.4 43
124.0165 35528.2 24
124.0404 2878.8 1
124.0769 5202.1 3
124.9881 28186.8 19
125.0244 25108.9 17
125.072 84277.6 57
126.0195 11479.5 7
126.0561 67411 45
134.0248 35829.9 24
135.0088 115683.8 78
135.0453 6692.7 4
136.0166 5374.7 3
136.0403 6687.6 4
136.0767 23425.9 15
136.988 6239.8 4
137.0244 53507.7 36
137.0481 9810.1 6
138.0195 6271.6 4
138.0323 15431.7 10
138.056 26788.4 18
138.0925 1933.3 1
139.015 16501.4 11
139.0274 2616.2 1
140.0355 14869.6 10
140.0718 20729.6 14
141.0193 17647.7 11
141.0667 5476.2 3
142.0145 114705.9 77
142.9985 85108.1 57
143.0826 18470.3 12
146.0374 1830.9 1
147.0451 41973.9 28
149.0121 4714.1 3
149.0237 2316.6 1
149.0481 9880.1 6
149.0607 29447 19
150.0197 53673.8 36
151.0038 17040.8 11
151.0276 8179.2 5
152.0115 4749.5 3
152.0353 81606.8 55
152.0717 48201.9 32
153.0196 10761.4 7
153.0434 1537.4 1
154.0384 17824.6 12
154.0874 16036.6 10
157.0659 7999.2 5
158.0371 8382.2 5
159.0451 26001.9 17
159.0815 29144.3 19
161.0245 22611.7 15
161.0608 28141.9 19
162.0197 18166.2 12
163.0038 81688.2 55
163.0275 12885 8
163.0765 7458.3 5
164.0117 31369.4 21
164.0355 8700 5
164.0592 5552.2 3
164.0717 43367.3 29
165.0193 2862.6 1
165.0432 6113.9 4
166.0146 2550 1
166.0511 2678.1 1
167.0224 21441.3 14
167.0463 6372.8 4
168.0303 68366 46
168.0666 77390.1 52
169.0142 2042 1
169.0254 28791 19
169.0616 35240.5 23
171.0454 2046.9 1
171.0818 8302.1 5
172.0529 22325.8 15
173.0607 424786.9 288
174.0323 2003.3 1
175.0403 2239.6 1
175.0765 5811.7 3
177.0304 8630.3 5
177.0669 2753.1 1
178.0145 31203.8 21
178.0508 5505.4 3
178.9987 16000.7 10
179.0826 13035.9 8
180.0302 38993.3 26
180.0666 46645 31
181.0382 13893.7 9
181.0614 11858.1 8
182.0821 27346.3 18
185.0607 18826 12
186.0688 14862.9 10
187.04 29585.9 20
187.0764 156521.1 106
188.048 6359.8 4
189.0563 2092.1 1
189.067 5905.7 4
189.0921 2592.2 1
192.0542 11933.4 8
194.0735 1709.1 1
195.041 7017.3 4
195.0775 10375.6 7
196.0252 16211.4 10
196.0531 32462.5 22
196.0616 4443.9 3
197.0608 14250.6 9
197.0927 28773.6 19
198.0771 4680.4 3
199.0399 9030.4 6
199.0764 19462.4 13
200.0482 2517.5 1
201.0558 37294.6 25
201.0924 6246.9 4
203.0715 70349.6 47
204.0422 1482.9 1
207.0774 53413.6 36
208.0611 11328.2 7
209.0608 19536 13
210.0687 31902 21
211.0403 22554.2 15
211.0765 103546.1 70
212.0479 12827.7 8
213.0556 26562.9 18
213.0919 20346.9 13
214.0273 10716.8 7
214.0638 6532.2 4
215.0346 1900.2 1
215.0714 8378.5 5
217.0506 362880.8 246
218.0588 2216.5 1
219.0813 4869.5 3
221.0614 2714.8 1
221.0974 8928 6
222.0686 8599.2 5
223.0767 45110.2 30
224.048 28672.1 19
224.0843 5265.3 3
225.056 27488.6 18
225.0922 47568.6 32
226.0635 18331.3 12
226.0728 4910.8 3
226.0875 1646.5 1
227.0351 4600.3 3
227.0714 63816.6 43
229.0506 75804.3 51
229.087 41173.9 27
231.0665 11117.2 7
232.0523 1701.7 1
233.0607 5881.4 3
234.0686 18154.1 12
235.0765 13311.7 9
236.0472 9577 6
237.056 20373.1 13
237.0921 29564.2 20
238.0635 25496.5 17
238.0874 5491.5 3
239.0714 103839.5 70
240.0429 900714.4 610
241.0509 19084 12
241.0871 143306.5 97
243.1026 11564.5 7
244.0377 1834.1 1
247.0762 26192.4 17
248.0479 4849.3 3
248.0719 10815.6 7
248.0839 2494.1 1
249.0554 15015.1 10
249.0918 22062.6 14
250.0635 34254.3 23
251.0713 62831.9 42
252.0427 2707.4 1
252.0669 2305.6 1
252.0792 8799.6 5
252.103 4779.2 3
253.0515 12053.9 8
253.0869 32357.7 21
254.0583 30437.3 20
255.0664 1473375.4 999
256.0979 4680.5 3
256.1343 4906.2 3
257.0459 18491.3 12
257.0817 20668.4 14
258.1139 1532.2 1
258.15 17469.4 11
260.0475 19662.7 13
261.0555 18126.7 12
262.0873 7980.9 5
263.0712 26624.6 18
264.0428 11706.7 7
264.0787 3029.7 2
264.1029 6500.7 4
265.0502 5441.2 3
265.087 73974.5 50
266.0584 7306.2 4
266.0952 8768 5
267.0663 50590.1 34
267.1029 7366.9 4
268.0741 2403.5 1
268.0979 5099.2 3
268.1345 18184 12
269.0819 100831.6 68
270.1132 2594.6 1
270.1491 5082 3
271.0616 2513.9 1
271.0976 8650.7 5
273.0769 218455.9 148
275.0715 48568.9 32
276.0427 6786.2 4
276.0653 1991.1 1
276.0795 5978.2 4
276.1036 2865.1 1
277.0505 27590.6 18
277.0867 5930.7 4
277.1104 2740.2 1
278.0585 42403.6 28
278.0823 3801.2 2
278.1188 13758.2 9
279.0661 38994.2 26
280.0379 5099.5 3
280.0745 2930.7 1
280.0978 21093.6 14
281.082 47561.3 32
281.1053 16669.3 11
282.0533 6463.8 4
282.0765 1724.6 1
282.1135 6300.2 4
283.097 15674.5 10
284.1291 16902.9 11
285.0768 27933.7 18
286.1445 7186.2 4
288.067 2455.9 1
290.0222 29799 20
290.0822 16652.4 11
291.0664 44836.1 30
292.037 1791 1
292.0746 14839.1 10
292.0976 1742.1 1
292.1341 8326.5 5
293.0459 6158 4
293.0821 67634.6 45
294.0537 5888.9 3
294.0899 17298.9 11
294.1142 13798.2 9
294.1499 10671.6 7
295.061 21139.3 14
295.0977 3125.7 2
296.093 2900.6 1
296.1292 48361.4 32
297.0768 61840.8 41
300.1244 10669.1 7
304.0372 2743.7 1
304.0614 5979.8 4
304.0976 2406.9 1
305.0454 37604.8 25
305.1051 10570.2 7
306.0761 10112.6 6
307.0612 8129.6 5
308.093 25512.3 17
308.1294 10273.5 6
309.0767 44705.3 30
310.145 38645.4 26
311.0928 10828.4 7
312.1242 15487.3 10
313.0722 1707.5 1
314.1395 2789.1 1
318.0772 6142.6 4
318.1138 3139 2
319.0621 13423.4 9
320.0695 6595.4 4
320.1285 9152.6 6
321.0629 1571.9 1
321.1008 5115.2 3
322.0485 16518.1 11
322.1093 4427.5 3
323.1178 4590 3
324.0874 1576.2 1
326.1037 1660.7 1
326.1396 23238.2 15
328.156 8131.3 5
334.072 6885.2 4
335.0555 4700.2 3
335.1397 2275.7 1
336.0874 5702 3
336.1241 27522.5 18
337.0722 12878.9 8
337.095 2843.7 1
338.0799 5640.7 3
338.1401 19715.3 13
340.1191 16535.4 11
349.0963 2608.1 1
353.1509 6147.9 4
354.1349 22675.8 15
356.1501 2182.6 1
358.1297 503370.8 341
362.068 1509.4 1
363.0506 2093.3 1
364.1194 2275.9 1
371.1619 7344.9 4
382.1298 10058.4 6
400.1405 3044.2 2
408.1088 7177 4
//
