4-{[3,5-Bis(methoxycarbonyl)-4,5-dihydro-1H-pyrazol-5-yl]methylamino}pyridine 1-oxide monohydrate
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021970/bv2013sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021970/bv2013Isup2.hkl |
CCDC reference: 613608
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: Please supply.
C13H16N4O5·H2O | Z = 2 |
Mr = 326.31 | F(000) = 344 |
Triclinic, P1 | Dx = 1.459 Mg m−3 |
Hall symbol: -P 1 | Mo - Kα radiation, λ = 0.71073 Å |
a = 6.0678 (7) Å | Cell parameters from 8766 reflections |
b = 8.7476 (9) Å | θ = 2–27° |
c = 15.0449 (18) Å | µ = 0.11 mm−1 |
α = 104.435 (6)° | T = 150 K |
β = 94.885 (6)° | Chunk, colourless |
γ = 103.676 (6)° | 0.40 × 0.35 × 0.29 mm |
V = 742.57 (15) Å3 |
Nonius KappaCCD diffractometer | 1906 reflections with I > 2.0σ(I) |
Graphite 002 monochromator | Rint = 0.029 |
ω scans | θmax = 27.8°, θmin = 2.5° |
Absorption correction: multi-scan (Otwinowski & Minor, 1997) | h = 0→7 |
Tmin = 0.936, Tmax = 0.969 | k = −11→11 |
8766 measured reflections | l = −19→19 |
2559 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0806P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.131 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.47 e Å−3 |
2559 reflections | Δρmin = −0.24 e Å−3 |
280 parameters |
Experimental. 1H NMR (d6-DMSO, 400 MHz): δ 8.88 (s, 1H), 7.81 (d, 2H, J = 7.7 Hz), 6.73 (t, 1H, J = 8.4 Hz), 6.60 (d, 2H, J = 7.3 Hz), 3.69 (s, 3H), 3.64 (s, 3H), 3.49 (d, 2H, J = 6.6 Hz), 3.37 (s, 2H), 3.21 (d, 1H, J = 17.6 Hz), 3.00 (d, 1H, J = 17.6 Hz); 13C NMR (d6-DMSO, 100 MHz): δ 172.2, 163.1, 147.5, 139.0, 138.5, 109.9, 73.8, 53.5, 52.2, 47.8, 38.1; IR (KBr, ν cm-1): 1735; ESMS C13H16N4O5Na+ requires m/z = 331.264, found m/z = 331.101. |
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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R_factor_obs 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 | ||
O(1) | 0.3739 (3) | 0.92493 (17) | 0.61361 (10) | 0.0353 (4) | |
O(1W) | 0.6188 (3) | 0.8263 (2) | 0.47558 (13) | 0.0358 (4) | |
O(91) | −0.3029 (3) | −0.0054 (2) | 0.83549 (11) | 0.0396 (4) | |
O(92) | 0.0516 (2) | 0.05867 (17) | 0.79991 (10) | 0.0297 (4) | |
O(121) | −0.1487 (3) | 0.69967 (18) | 0.96714 (10) | 0.0353 (4) | |
O(122) | −0.5292 (3) | 0.62268 (18) | 0.91620 (11) | 0.0365 (4) | |
N(1) | 0.2422 (3) | 0.7822 (2) | 0.62159 (12) | 0.0274 (4) | |
N(7) | −0.1541 (3) | 0.3372 (2) | 0.63695 (13) | 0.0301 (4) | |
N(10) | −0.4357 (3) | 0.2115 (2) | 0.75419 (14) | 0.0358 (5) | |
N(11) | −0.4930 (3) | 0.3438 (2) | 0.80260 (12) | 0.0300 (5) | |
C(2) | 0.3380 (4) | 0.6909 (3) | 0.66583 (15) | 0.0283 (5) | |
C(3) | 0.2142 (4) | 0.5445 (3) | 0.67368 (15) | 0.0273 (5) | |
C(4) | −0.0204 (3) | 0.4838 (2) | 0.63575 (13) | 0.0244 (5) | |
C(5) | −0.1150 (4) | 0.5846 (3) | 0.59284 (14) | 0.0272 (5) | |
C(6) | 0.0174 (4) | 0.7298 (3) | 0.58598 (14) | 0.0279 (5) | |
C(8) | −0.0880 (4) | 0.2203 (3) | 0.67996 (15) | 0.0262 (5) | |
C(9) | −0.1877 (3) | 0.2231 (2) | 0.77078 (14) | 0.0265 (5) | |
C(12) | −0.3076 (3) | 0.4467 (2) | 0.85505 (14) | 0.0249 (5) | |
C(13) | −0.0975 (4) | 0.3877 (3) | 0.84731 (17) | 0.0326 (6) | |
C(91) | −0.1571 (3) | 0.0796 (3) | 0.80603 (14) | 0.0266 (5) | |
C(93) | 0.1021 (4) | −0.0683 (3) | 0.83872 (18) | 0.0336 (6) | |
C(121) | −0.3188 (4) | 0.6015 (3) | 0.91833 (15) | 0.0286 (5) | |
C(123) | −0.5433 (5) | 0.7740 (3) | 0.97963 (18) | 0.0351 (6) | |
H(2) | 0.490 (4) | 0.738 (3) | 0.6911 (15) | 0.031 (6)* | |
H(3) | 0.296 (4) | 0.487 (2) | 0.7035 (14) | 0.026 (5)* | |
H(5) | −0.284 (4) | 0.552 (3) | 0.5656 (16) | 0.036 (6)* | |
H(6) | −0.026 (3) | 0.803 (2) | 0.5573 (14) | 0.020 (5)* | |
H(7) | −0.296 (5) | 0.312 (3) | 0.6130 (17) | 0.041 (7)* | |
H(10) | −0.560 (5) | 0.111 (4) | 0.717 (2) | 0.078 (10)* | |
H(81) | −0.157 (4) | 0.112 (3) | 0.6336 (16) | 0.037 (6)* | |
H(82) | 0.066 (4) | 0.244 (3) | 0.6918 (15) | 0.025 (6)* | |
H(131) | 0.045 (4) | 0.437 (3) | 0.8300 (15) | 0.029 (6)* | |
H(132) | −0.042 (4) | 0.372 (3) | 0.9028 (18) | 0.036 (6)* | |
H(1W1) | 0.550 (5) | 0.863 (4) | 0.520 (2) | 0.061 (10)* | |
H(1W2) | 0.670 (6) | 0.902 (4) | 0.458 (2) | 0.067 (11)* | |
H(231) | −0.472 (4) | 0.786 (3) | 1.0431 (18) | 0.038 (6)* | |
H(232) | −0.461 (4) | 0.867 (3) | 0.9631 (15) | 0.033 (6)* | |
H(233) | −0.703 (5) | 0.756 (3) | 0.9738 (19) | 0.057 (8)* | |
H(931) | 0.095 (4) | −0.049 (3) | 0.9083 (16) | 0.037 (6)* | |
H(932) | 0.260 (4) | −0.062 (3) | 0.8374 (15) | 0.029 (6)* | |
H(933) | −0.004 (4) | −0.175 (3) | 0.8020 (16) | 0.033 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O(1) | 0.0459 (10) | 0.0199 (7) | 0.0359 (9) | −0.0021 (7) | 0.0073 (7) | 0.0100 (6) |
O(1W) | 0.0330 (10) | 0.0362 (10) | 0.0379 (10) | 0.0074 (8) | 0.0010 (8) | 0.0134 (8) |
O(91) | 0.0267 (9) | 0.0483 (10) | 0.0497 (10) | 0.0055 (8) | 0.0119 (8) | 0.0267 (8) |
O(92) | 0.0251 (8) | 0.0311 (8) | 0.0388 (9) | 0.0077 (7) | 0.0093 (7) | 0.0185 (7) |
O(121) | 0.0335 (9) | 0.0320 (8) | 0.0362 (9) | 0.0044 (7) | −0.0008 (7) | 0.0078 (7) |
O(122) | 0.0285 (9) | 0.0330 (9) | 0.0450 (10) | 0.0083 (7) | 0.0035 (7) | 0.0060 (7) |
N(1) | 0.0342 (11) | 0.0215 (9) | 0.0255 (9) | 0.0033 (8) | 0.0055 (8) | 0.0085 (7) |
N(7) | 0.0233 (10) | 0.0290 (10) | 0.0357 (11) | −0.0007 (8) | −0.0030 (9) | 0.0144 (8) |
N(10) | 0.0256 (11) | 0.0353 (11) | 0.0426 (11) | 0.0108 (9) | 0.0028 (9) | 0.0026 (9) |
N(11) | 0.0303 (10) | 0.0269 (9) | 0.0328 (10) | 0.0052 (8) | 0.0017 (8) | 0.0115 (8) |
C(2) | 0.0255 (12) | 0.0266 (11) | 0.0310 (12) | 0.0037 (10) | 0.0007 (10) | 0.0090 (9) |
C(3) | 0.0277 (12) | 0.0241 (11) | 0.0299 (12) | 0.0067 (10) | 0.0003 (9) | 0.0088 (9) |
C(4) | 0.0265 (11) | 0.0226 (10) | 0.0221 (11) | 0.0042 (9) | 0.0022 (9) | 0.0052 (8) |
C(5) | 0.0284 (12) | 0.0278 (11) | 0.0241 (11) | 0.0071 (10) | 0.0000 (9) | 0.0066 (9) |
C(6) | 0.0347 (13) | 0.0256 (11) | 0.0240 (11) | 0.0098 (10) | 0.0013 (9) | 0.0076 (9) |
C(8) | 0.0247 (13) | 0.0225 (11) | 0.0299 (12) | 0.0015 (9) | 0.0019 (10) | 0.0096 (9) |
C(9) | 0.0243 (11) | 0.0265 (11) | 0.0274 (11) | 0.0058 (9) | 0.0028 (9) | 0.0061 (9) |
C(12) | 0.0261 (11) | 0.0245 (11) | 0.0257 (11) | 0.0062 (9) | 0.0038 (9) | 0.0106 (9) |
C(13) | 0.0297 (13) | 0.0347 (13) | 0.0298 (13) | 0.0057 (11) | −0.0002 (11) | 0.0066 (10) |
C(91) | 0.0241 (12) | 0.0304 (11) | 0.0231 (11) | 0.0047 (10) | 0.0026 (9) | 0.0063 (9) |
C(93) | 0.0328 (14) | 0.0346 (14) | 0.0409 (15) | 0.0130 (12) | 0.0068 (11) | 0.0199 (11) |
C(121) | 0.0291 (12) | 0.0299 (12) | 0.0313 (12) | 0.0068 (10) | 0.0053 (10) | 0.0171 (10) |
C(123) | 0.0398 (15) | 0.0270 (13) | 0.0412 (15) | 0.0128 (12) | 0.0143 (12) | 0.0082 (11) |
O(1)—N(1) | 1.353 (2) | C(3)—H(3) | 0.94 (2) |
O(1W)—H(1W1) | 0.85 (3) | C(4)—C(5) | 1.409 (3) |
O(1W)—H(1W2) | 0.78 (4) | C(5)—C(6) | 1.366 (3) |
O(91)—C(91) | 1.205 (3) | C(5)—H(5) | 1.02 (2) |
O(92)—C(91) | 1.329 (2) | C(6)—H(6) | 0.93 (2) |
O(92)—C(93) | 1.457 (3) | C(8)—C(9) | 1.538 (3) |
O(121)—C(121) | 1.217 (3) | C(8)—H(81) | 1.00 (2) |
O(122)—C(121) | 1.331 (3) | C(8)—H(82) | 0.90 (2) |
O(122)—C(123) | 1.452 (3) | C(9)—C(91) | 1.522 (3) |
N(1)—C(6) | 1.347 (3) | C(9)—C(13) | 1.547 (3) |
N(1)—C(2) | 1.356 (3) | C(12)—C(121) | 1.468 (3) |
N(7)—C(4) | 1.351 (3) | C(12)—C(13) | 1.487 (3) |
N(7)—C(8) | 1.451 (3) | C(13)—H(131) | 0.96 (2) |
N(7)—H(7) | 0.86 (3) | C(13)—H(132) | 0.93 (3) |
N(10)—N(11) | 1.343 (3) | C(93)—H(931) | 1.02 (2) |
N(10)—C(9) | 1.479 (3) | C(93)—H(932) | 0.95 (2) |
N(10)—H(10) | 1.02 (3) | C(93)—H(933) | 0.99 (3) |
N(11)—C(12) | 1.309 (3) | C(123)—H(231) | 0.99 (3) |
C(2)—C(3) | 1.362 (3) | C(123)—H(232) | 0.95 (3) |
C(2)—H(2) | 0.92 (2) | C(123)—H(233) | 0.94 (3) |
C(3)—C(4) | 1.410 (3) | ||
H(1W1)—O(1W)—H(1W2) | 105 (3) | N(10)—C(9)—C(91) | 108.65 (17) |
C(91)—O(92)—C(93) | 115.16 (17) | N(10)—C(9)—C(8) | 109.51 (17) |
C(121)—O(122)—C(123) | 114.36 (18) | C(91)—C(9)—C(8) | 110.79 (16) |
C(6)—N(1)—O(1) | 120.82 (17) | N(10)—C(9)—C(13) | 101.45 (15) |
C(6)—N(1)—C(2) | 119.67 (19) | C(91)—C(9)—C(13) | 111.65 (17) |
O(1)—N(1)—C(2) | 119.50 (18) | C(8)—C(9)—C(13) | 114.28 (18) |
C(4)—N(7)—C(8) | 126.94 (19) | N(11)—C(12)—C(121) | 120.68 (18) |
C(4)—N(7)—H(7) | 117.5 (17) | N(11)—C(12)—C(13) | 114.16 (17) |
C(8)—N(7)—H(7) | 115.4 (17) | C(121)—C(12)—C(13) | 125.09 (19) |
N(11)—N(10)—C(9) | 113.87 (18) | C(12)—C(13)—C(9) | 101.95 (17) |
N(11)—N(10)—H(10) | 119.9 (17) | C(12)—C(13)—H(131) | 129.1 (13) |
C(9)—N(10)—H(10) | 125.9 (17) | C(9)—C(13)—H(131) | 103.4 (13) |
C(12)—N(11)—N(10) | 108.36 (17) | C(12)—C(13)—H(132) | 111.2 (14) |
N(1)—C(2)—C(3) | 121.8 (2) | C(9)—C(13)—H(132) | 111.3 (14) |
N(1)—C(2)—H(2) | 114.2 (14) | H(131)—C(13)—H(132) | 99 (2) |
C(3)—C(2)—H(2) | 124.0 (14) | O(91)—C(91)—O(92) | 123.88 (19) |
C(2)—C(3)—C(4) | 120.3 (2) | O(91)—C(91)—C(9) | 124.69 (18) |
C(2)—C(3)—H(3) | 116.3 (13) | O(92)—C(91)—C(9) | 111.43 (17) |
C(4)—C(3)—H(3) | 123.4 (13) | O(92)—C(93)—H(931) | 114.9 (12) |
N(7)—C(4)—C(5) | 119.44 (19) | O(92)—C(93)—H(932) | 107.1 (13) |
N(7)—C(4)—C(3) | 124.39 (19) | H(931)—C(93)—H(932) | 101.3 (18) |
C(5)—C(4)—C(3) | 116.17 (19) | O(92)—C(93)—H(933) | 107.9 (13) |
C(6)—C(5)—C(4) | 121.2 (2) | H(931)—C(93)—H(933) | 111.1 (19) |
C(6)—C(5)—H(5) | 117.4 (13) | H(932)—C(93)—H(933) | 114.6 (18) |
C(4)—C(5)—H(5) | 121.4 (13) | O(121)—C(121)—O(122) | 124.30 (19) |
N(1)—C(6)—C(5) | 120.9 (2) | O(121)—C(121)—C(12) | 121.89 (19) |
N(1)—C(6)—H(6) | 111.2 (13) | O(122)—C(121)—C(12) | 113.81 (19) |
C(5)—C(6)—H(6) | 128.0 (13) | O(122)—C(123)—H(231) | 110.7 (13) |
N(7)—C(8)—C(9) | 110.97 (17) | O(122)—C(123)—H(232) | 111.6 (13) |
N(7)—C(8)—H(81) | 104.6 (13) | H(231)—C(123)—H(232) | 106 (2) |
C(9)—C(8)—H(81) | 109.6 (14) | O(122)—C(123)—H(233) | 100.0 (17) |
N(7)—C(8)—H(82) | 109.5 (14) | H(231)—C(123)—H(233) | 113 (2) |
C(9)—C(8)—H(82) | 109.6 (14) | H(232)—C(123)—H(233) | 116 (2) |
H(81)—C(8)—H(82) | 112.5 (18) | ||
C(9)—N(10)—N(11)—C(12) | −2.3 (2) | N(10)—N(11)—C(12)—C(13) | −1.1 (3) |
C(6)—N(1)—C(2)—C(3) | 1.5 (3) | N(11)—C(12)—C(13)—C(9) | 3.7 (3) |
O(1)—N(1)—C(2)—C(3) | −178.33 (18) | C(121)—C(12)—C(13)—C(9) | −179.45 (19) |
N(1)—C(2)—C(3)—C(4) | −0.3 (3) | N(10)—C(9)—C(13)—C(12) | −4.4 (2) |
C(8)—N(7)—C(4)—C(5) | −178.14 (18) | C(91)—C(9)—C(13)—C(12) | −119.95 (19) |
C(8)—N(7)—C(4)—C(3) | 3.1 (3) | C(8)—C(9)—C(13)—C(12) | 113.3 (2) |
C(2)—C(3)—C(4)—N(7) | 177.26 (19) | C(93)—O(92)—C(91)—O(91) | −4.8 (3) |
C(2)—C(3)—C(4)—C(5) | −1.6 (3) | C(93)—O(92)—C(91)—C(9) | 175.53 (17) |
N(7)—C(4)—C(5)—C(6) | −176.60 (18) | N(10)—C(9)—C(91)—O(91) | −15.6 (3) |
C(3)—C(4)—C(5)—C(6) | 2.3 (3) | C(8)—C(9)—C(91)—O(91) | −135.9 (2) |
O(1)—N(1)—C(6)—C(5) | 179.05 (17) | C(13)—C(9)—C(91)—O(91) | 95.5 (2) |
C(2)—N(1)—C(6)—C(5) | −0.8 (3) | N(10)—C(9)—C(91)—O(92) | 164.09 (16) |
C(4)—C(5)—C(6)—N(1) | −1.1 (3) | C(8)—C(9)—C(91)—O(92) | 43.8 (2) |
C(4)—N(7)—C(8)—C(9) | 104.6 (2) | C(13)—C(9)—C(91)—O(92) | −84.9 (2) |
N(11)—N(10)—C(9)—C(91) | 122.11 (18) | C(123)—O(122)—C(121)—O(121) | −1.4 (3) |
N(11)—N(10)—C(9)—C(8) | −116.76 (19) | C(123)—O(122)—C(121)—C(12) | 179.01 (18) |
N(11)—N(10)—C(9)—C(13) | 4.4 (2) | N(11)—C(12)—C(121)—O(121) | −179.3 (2) |
N(7)—C(8)—C(9)—N(10) | 49.4 (2) | C(13)—C(12)—C(121)—O(121) | 4.0 (3) |
N(7)—C(8)—C(9)—C(91) | 169.25 (17) | N(11)—C(12)—C(121)—O(122) | 0.3 (3) |
N(7)—C(8)—C(9)—C(13) | −63.6 (2) | C(13)—C(12)—C(121)—O(122) | −176.4 (2) |
N(10)—N(11)—C(12)—C(121) | −178.12 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N(7)—H(7)···O(1W)i | 0.86 (3) | 2.17 (2) | 2.989 (4) | 159 (2) |
N(10)—H(10)···O(1)ii | 1.01 (3) | 1.88 (3) | 2.768 (3) | 144 (3) |
O(1W)—H(1W1)···O(1) | 0.85 (3) | 1.89 (3) | 2.739 (3) | 174 (3) |
O(1W)—H(1W2)···O(1)iii | 0.78 (4) | 2.12 (4) | 2.821 (3) | 150 (3) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y−1, z; (iii) −x+1, −y+2, −z+1. |