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
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.131
- Data-to-parameter ratio = 9.1
checkCIF/PLATON results
No syntax errors found
Alert level B ABSMU01_ALERT_1_B The ratio of given/expected absorption coefficient lies outside the range 0.95 <> 1.05 Calculated value of mu = 0.117 Value of mu given = 0.109
Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.6569 Proportion of unique data used 0.7925 Ratio reflections to parameters 9.1393 PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.14 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.90 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C12 - C121 .. 5.68 su PLAT320_ALERT_2_C Check Hybridisation of C13 in Main Residue . ? PLAT353_ALERT_3_C Long N-H Bond (0.87A) N10 - H10 ... 1.01 Ang. PLAT390_ALERT_3_C Deviating Methyl C123 X-C-H Bond Angle ...... 100.00 Deg. PLAT391_ALERT_3_C Deviating Methyl C93 H-C-H Bond Angle ...... 101.20 Deg. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H16 N4 O5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
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. |
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