Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017683/cm6017sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017683/cm6017Isup2.hkl |
CCDC reference: 198982
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.107
- Data-to-parameter ratio = 8.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.325 0.593 Tmin' and Tmax expected: 0.373 0.593 RR' = 0.872 Please check that your absorption correction is appropriate. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 69.02 From the CIF: _reflns_number_total 2350 Count of symmetry unique reflns 2234 Completeness (_total/calc) 105.19% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 116 Fraction of Friedel pairs measured 0.052 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
The title compound was obtained from the Janssen Rechearch Foundation, Beerse, Belgium. The synthesis has been described by Heykants et al. (1999). Single crystals were grown by slow evaporation from a solution in methanol–water.
The positions of the H atoms of the water molecule were obtained with the program HYDROGEN (Nardelli, 1999). Those of the OH and methyl groups were found from a circular difference Fourier synthesis. The remaining H atoms were calculated geometrically. All H atoms were included in the refinement, but constrained to ride on their parent atoms. The isotropic displacement parameters of the H atoms were fixed at 1.25Ueq of their parent atoms.
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PARST (Nardelli, 1983), PLATON (Spek, 1998) and WinGX (Farrugia, 1999).
Fig. 1. Perspective view of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
C14H21ClN3O3+·C4H5O6−·H2O | F(000) = 508 |
Mr = 481.89 | Dx = 1.407 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
a = 7.6086 (4) Å | Cell parameters from 39 reflections |
b = 10.664 (1) Å | θ = 10.8–28.0° |
c = 14.0482 (6) Å | µ = 2.01 mm−1 |
β = 93.980 (6)° | T = 293 K |
V = 1137.1 (1) Å3 | Block, colourless |
Z = 2 | 0.45 × 0.30 × 0.26 mm |
Siemens P4 four-circle diffractometer | Rint = 0.033 |
ω/2θ scans | θmax = 69.0° |
Absorption correction: ψ scan (XEMP; Siemens, 1989) | h = −1→8 |
Tmin = 0.325, Tmax = 0.593 | k = −1→12 |
2935 measured reflections | l = −17→17 |
2350 independent reflections | 3 standard reflections every 100 reflections |
2280 reflections with F2 > 2σ(F2) | intensity decay: none |
Refinement on F2 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.2043P] where P = (Fo2 + 2Fc2)/3 |
Least-squares matrix: full | (Δ/σ)max < 0.001 |
R[F2 > 2σ(F2)] = 0.037 | Δρmax = 0.21 e Å−3 |
wR(F2) = 0.107 | Δρmin = −0.26 e Å−3 |
S = 1.06 | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin((2θ)]-1/4 |
2350 reflections | Extinction coefficient: 0.026 (2) |
295 parameters | Absolute structure: Flack (1983), 220 Friedel pairs |
H-atom parameters constrained | Absolute structure parameter: −0.01 (2) |
C14H21ClN3O3+·C4H5O6−·H2O | V = 1137.1 (1) Å3 |
Mr = 481.89 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 7.6086 (4) Å | µ = 2.01 mm−1 |
b = 10.664 (1) Å | T = 293 K |
c = 14.0482 (6) Å | 0.45 × 0.30 × 0.26 mm |
β = 93.980 (6)° |
Siemens P4 four-circle diffractometer | 2280 reflections with F2 > 2σ(F2) |
Absorption correction: ψ scan (XEMP; Siemens, 1989) | Rint = 0.033 |
Tmin = 0.325, Tmax = 0.593 | 3 standard reflections every 100 reflections |
2935 measured reflections | intensity decay: none |
2350 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.107 | Δρmax = 0.21 e Å−3 |
S = 1.06 | Δρmin = −0.26 e Å−3 |
2350 reflections | Absolute structure: Flack (1983), 220 Friedel pairs |
295 parameters | Absolute structure parameter: −0.01 (2) |
x | y | z | Uiso*/Ueq | ||
N1 | 1.0233 (3) | 0.8441 (3) | 0.5720 (2) | 0.0472 (8)* | |
C2 | 0.9115 (5) | 0.9582 (4) | 0.5754 (2) | 0.052 (1)* | |
C3 | 0.8016 (4) | 0.9525 (3) | 0.6611 (2) | 0.0445 (8)* | |
C4 | 0.6873 (4) | 0.8348 (3) | 0.6578 (2) | 0.0443 (8)* | |
C5 | 0.7988 (4) | 0.7178 (3) | 0.6499 (2) | 0.0472 (9)* | |
C6 | 0.9171 (4) | 0.7267 (4) | 0.5667 (2) | 0.051 (1)* | |
O7 | 0.9111 (3) | 0.9443 (2) | 0.7472 (1) | 0.0496 (6)* | |
C8 | 0.9896 (8) | 1.0584 (5) | 0.7775 (4) | 0.094 (2)* | |
N9 | 0.5907 (3) | 0.8322 (3) | 0.7439 (2) | 0.0509 (9)* | |
C10 | 0.4270 (4) | 0.7920 (3) | 0.7488 (2) | 0.043 (1)* | |
O11 | 0.3413 (3) | 0.7443 (2) | 0.6784 (1) | 0.0489 (6)* | |
C12 | 0.3447 (3) | 0.8048 (3) | 0.8414 (2) | 0.0416 (9)* | |
C13 | 0.4104 (4) | 0.8751 (3) | 0.9209 (2) | 0.0468 (9)* | |
C14 | 0.3177 (4) | 0.8832 (4) | 1.0018 (2) | 0.0506 (9)* | |
C15 | 0.1554 (4) | 0.8235 (3) | 1.0080 (2) | 0.0494 (9)* | |
C16 | 0.0901 (4) | 0.7531 (3) | 0.9287 (2) | 0.0469 (9)* | |
C17 | 0.1846 (4) | 0.7434 (3) | 0.8483 (2) | 0.0430 (8)* | |
O18 | 0.5680 (3) | 0.9344 (3) | 0.9141 (2) | 0.0615 (8)* | |
C19 | 0.6417 (6) | 1.0067 (6) | 0.9924 (3) | 0.083 (2)* | |
N20 | 0.0663 (5) | 0.8328 (4) | 1.0882 (2) | 0.071 (1)* | |
Cl21 | −0.1091 (1) | 0.6751 (1) | 0.93367 (7) | 0.0695 (3)* | |
O22 | 0.7777 (4) | 0.3019 (4) | 0.5790 (2) | 0.076 (1)* | |
O23 | 0.8168 (3) | 0.4087 (3) | 0.7152 (2) | 0.0561 (8)* | |
C24 | 0.7273 (4) | 0.3465 (4) | 0.6541 (2) | 0.0474 (9)* | |
C25 | 0.5358 (4) | 0.3187 (3) | 0.6734 (2) | 0.0467 (9)* | |
O26 | 0.4549 (3) | 0.2500 (3) | 0.5963 (2) | 0.0650 (9)* | |
C27 | 0.4360 (4) | 0.4391 (3) | 0.6895 (2) | 0.0434 (9)* | |
O28 | 0.4358 (3) | 0.5134 (2) | 0.6063 (2) | 0.0475 (7)* | |
C29 | 0.2509 (4) | 0.4065 (3) | 0.7192 (2) | 0.047 (1)* | |
O30 | 0.1244 (3) | 0.4570 (3) | 0.6666 (2) | 0.0628 (8)* | |
O31 | 0.2339 (3) | 0.3397 (4) | 0.7876 (2) | 0.081 (1)* | |
O32 | 0.3290 (5) | 0.0093 (4) | 0.5658 (3) | 0.109 (2)* | |
H1A | 1.0982 | 0.8417 | 0.6244 | 0.059* | |
H1B | 1.0877 | 0.8485 | 0.5207 | 0.059* | |
H2A | 0.8349 | 0.9639 | 0.5174 | 0.065* | |
H2B | 0.9857 | 1.0322 | 0.5795 | 0.065* | |
H3 | 0.7268 | 1.0272 | 0.6625 | 0.056* | |
H4 | 0.6027 | 0.8395 | 0.6020 | 0.055* | |
H5A | 0.7224 | 0.6454 | 0.6411 | 0.059* | |
H5B | 0.8714 | 0.7062 | 0.7088 | 0.059* | |
H6A | 0.9954 | 0.6549 | 0.5678 | 0.064* | |
H6B | 0.8449 | 0.7249 | 0.5070 | 0.064* | |
H8A | 1.0636 | 1.0446 | 0.8347 | 0.117* | |
H8B | 0.8994 | 1.1179 | 0.7901 | 0.117* | |
H8C | 1.0592 | 1.0904 | 0.7286 | 0.117* | |
H9 | 0.6446 | 0.8589 | 0.7958 | 0.064* | |
H14 | 0.3645 | 0.9297 | 1.0536 | 0.063* | |
H17 | 0.1398 | 0.6945 | 0.7974 | 0.054* | |
H19A | 0.7553 | 1.0375 | 0.9779 | 0.104* | |
H19B | 0.6540 | 0.9551 | 1.0485 | 0.104* | |
H19C | 0.5655 | 1.0761 | 1.0036 | 0.104* | |
H20A | 0.1097 | 0.8759 | 1.1359 | 0.089* | |
H20B | −0.0334 | 0.7957 | 1.0912 | 0.089* | |
H25 | 0.5348 | 0.2672 | 0.7312 | 0.058* | |
H26 | 0.5276 | 0.2355 | 0.5572 | 0.081* | |
H27 | 0.4983 | 0.4851 | 0.7420 | 0.054* | |
H28 | 0.4080 | 0.5855 | 0.6188 | 0.059* | |
H30 | 0.0299 | 0.4393 | 0.6880 | 0.078* | |
H32A | 0.3552 | 0.0810 | 0.5891 | 0.137* | |
H32B | 0.3534 | 0.0097 | 0.5077 | 0.137* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.035 (1) | 0.068 (2) | 0.040 (1) | −0.003 (1) | 0.0108 (9) | 0.001 (1) |
C2 | 0.052 (2) | 0.061 (2) | 0.045 (2) | −0.001 (2) | 0.009 (1) | 0.009 (1) |
C3 | 0.040 (2) | 0.053 (2) | 0.041 (1) | 0.004 (1) | 0.007 (1) | 0.001 (1) |
C4 | 0.031 (1) | 0.068 (2) | 0.035 (1) | −0.002 (1) | 0.0071 (9) | −0.005 (1) |
C5 | 0.044 (2) | 0.054 (2) | 0.045 (1) | −0.007 (1) | 0.009 (1) | −0.005 (1) |
C6 | 0.044 (2) | 0.062 (2) | 0.049 (2) | −0.002 (1) | 0.014 (1) | −0.011 (1) |
O7 | 0.049 (1) | 0.056 (1) | 0.043 (1) | −0.005 (1) | −0.0005 (8) | −0.005 (1) |
C8 | 0.123 (4) | 0.068 (3) | 0.087 (3) | −0.026 (3) | −0.023 (3) | −0.016 (2) |
N9 | 0.029 (1) | 0.090 (2) | 0.035 (1) | −0.006 (1) | 0.0060 (8) | −0.010 (1) |
C10 | 0.037 (2) | 0.055 (2) | 0.038 (1) | 0.003 (1) | 0.005 (1) | −0.004 (1) |
O11 | 0.041 (1) | 0.064 (1) | 0.041 (1) | −0.003 (1) | 0.0038 (7) | −0.010 (1) |
C12 | 0.030 (1) | 0.055 (2) | 0.040 (1) | 0.002 (1) | 0.007 (1) | −0.003 (1) |
C13 | 0.043 (2) | 0.056 (2) | 0.042 (1) | −0.002 (1) | 0.007 (1) | −0.008 (1) |
C14 | 0.048 (2) | 0.063 (2) | 0.042 (1) | −0.001 (2) | 0.008 (1) | −0.008 (1) |
C15 | 0.051 (2) | 0.058 (2) | 0.041 (1) | 0.008 (1) | 0.017 (1) | 0.005 (1) |
C16 | 0.035 (2) | 0.059 (2) | 0.047 (1) | 0.003 (1) | 0.011 (1) | 0.008 (1) |
C17 | 0.035 (2) | 0.053 (2) | 0.041 (1) | 0.002 (1) | 0.003 (1) | 0.001 (1) |
O18 | 0.048 (1) | 0.087 (2) | 0.050 (1) | −0.022 (1) | 0.0130 (9) | −0.024 (1) |
C19 | 0.074 (3) | 0.110 (4) | 0.066 (2) | −0.031 (3) | 0.008 (2) | −0.035 (3) |
N20 | 0.072 (2) | 0.093 (2) | 0.052 (1) | −0.006 (2) | 0.032 (1) | −0.002 (2) |
Cl21 | 0.0483 (5) | 0.0927 (7) | 0.0693 (5) | −0.0162 (4) | 0.0172 (3) | 0.0086 (5) |
O22 | 0.057 (2) | 0.111 (2) | 0.064 (1) | −0.009 (2) | 0.032 (1) | −0.015 (2) |
O23 | 0.029 (1) | 0.083 (2) | 0.056 (1) | −0.003 (1) | 0.0063 (8) | 0.001 (1) |
C24 | 0.030 (1) | 0.065 (2) | 0.047 (1) | 0.003 (1) | 0.011 (1) | 0.006 (1) |
C25 | 0.035 (2) | 0.056 (2) | 0.049 (2) | −0.004 (1) | 0.008 (1) | 0.001 (1) |
O26 | 0.048 (1) | 0.069 (2) | 0.078 (2) | −0.007 (1) | 0.004 (1) | −0.020 (1) |
C27 | 0.031 (2) | 0.061 (2) | 0.039 (1) | −0.006 (1) | 0.009 (1) | −0.005 (1) |
O28 | 0.037 (1) | 0.054 (1) | 0.053 (1) | −0.0037 (9) | 0.0135 (8) | −0.001 (1) |
C29 | 0.028 (1) | 0.072 (2) | 0.043 (1) | −0.001 (1) | 0.009 (1) | −0.001 (1) |
O30 | 0.026 (1) | 0.098 (2) | 0.065 (1) | −0.002 (1) | 0.0074 (9) | 0.021 (1) |
O31 | 0.042 (1) | 0.136 (3) | 0.067 (1) | 0.005 (2) | 0.019 (1) | 0.039 (2) |
O32 | 0.105 (3) | 0.072 (2) | 0.149 (3) | −0.017 (2) | 0.000 (2) | 0.003 (3) |
N1—H1A | 0.900 | C14—H14 | 0.930 |
N1—H1B | 0.900 | C14—C15 | 1.398 (5) |
N1—C2 | 1.487 (5) | C15—C16 | 1.404 (4) |
N1—C6 | 1.489 (5) | C15—N20 | 1.358 (5) |
C2—H2A | 0.970 | C16—C17 | 1.384 (4) |
C2—H2B | 0.970 | C16—Cl21 | 1.735 (3) |
C2—C3 | 1.513 (4) | C17—H17 | 0.930 |
C3—H3 | 0.980 | O18—C19 | 1.427 (5) |
C3—C4 | 1.526 (5) | C19—H19A | 0.960 |
C3—O7 | 1.423 (3) | C19—H19B | 0.960 |
C4—H4 | 0.980 | C19—H19C | 0.960 |
C4—C5 | 1.517 (5) | N20—H20A | 0.860 |
C4—N9 | 1.459 (4) | N20—H20B | 0.860 |
C5—H5A | 0.970 | O22—C24 | 1.242 (4) |
C5—H5B | 0.970 | O23—C24 | 1.249 (4) |
C5—C6 | 1.527 (5) | C24—C25 | 1.529 (4) |
C6—H6A | 0.970 | C25—H25 | 0.980 |
C6—H6B | 0.970 | C25—O26 | 1.413 (4) |
O7—C8 | 1.408 (6) | C25—C27 | 1.517 (5) |
C8—H8A | 0.960 | O26—H26 | 0.820 |
C8—H8B | 0.960 | C27—H27 | 0.980 |
C8—H8C | 0.960 | C27—O28 | 1.412 (4) |
N9—H9 | 0.860 | C27—C29 | 1.536 (4) |
N9—C10 | 1.323 (4) | O28—H28 | 0.820 |
C10—O11 | 1.254 (3) | C29—O30 | 1.290 (4) |
C10—C12 | 1.488 (4) | C29—O31 | 1.210 (5) |
C12—C13 | 1.408 (4) | O30—H30 | 0.820 |
C12—C17 | 1.392 (4) | O32—H32A | 0.850 |
C13—C14 | 1.382 (4) | O32—H32B | 0.850 |
C13—O18 | 1.364 (4) | ||
H1A—N1—H1B | 107.9 | C10—C12—C17 | 116.2 (2) |
H1A—N1—C2 | 109.1 | C13—C12—C17 | 117.3 (3) |
H1A—N1—C6 | 109.1 | C12—C13—C14 | 120.9 (3) |
H1B—N1—C2 | 109.1 | C12—C13—O18 | 117.2 (3) |
H1B—N1—C6 | 109.1 | C14—C13—O18 | 122.0 (3) |
C2—N1—C6 | 112.3 (3) | C13—C14—H14 | 119.1 |
N1—C2—H2A | 109.7 | C13—C14—C15 | 121.7 (3) |
N1—C2—H2B | 109.7 | H14—C14—C15 | 119.1 |
N1—C2—C3 | 110.0 (3) | C14—C15—C16 | 117.4 (3) |
H2A—C2—H2B | 108.2 | C14—C15—N20 | 120.8 (3) |
H2A—C2—C3 | 109.7 | C16—C15—N20 | 121.9 (3) |
H2B—C2—C3 | 109.7 | C15—C16—C17 | 120.8 (3) |
C2—C3—H3 | 109.8 | C15—C16—Cl21 | 119.1 (2) |
C2—C3—C4 | 110.8 (3) | C17—C16—Cl21 | 120.1 (2) |
C2—C3—O7 | 110.8 (2) | C12—C17—C16 | 121.9 (3) |
H3—C3—C4 | 109.8 | C12—C17—H17 | 119.1 |
H3—C3—O7 | 109.8 | C16—C17—H17 | 119.0 |
C4—C3—O7 | 105.9 (2) | C13—O18—C19 | 119.8 (3) |
C3—C4—H4 | 108.9 | O18—C19—H19A | 109.5 |
C3—C4—C5 | 111.0 (3) | O18—C19—H19B | 109.5 |
C3—C4—N9 | 108.0 (2) | O18—C19—H19C | 109.5 |
H4—C4—C5 | 108.9 | H19A—C19—H19B | 109.5 |
H4—C4—N9 | 108.9 | H19A—C19—H19C | 109.5 |
C5—C4—N9 | 111.2 (2) | H19B—C19—H19C | 109.5 |
C4—C5—H5A | 109.3 | C15—N20—H20A | 120.0 |
C4—C5—H5B | 109.3 | C15—N20—H20B | 120.0 |
C4—C5—C6 | 111.5 (3) | H20A—N20—H20B | 120.0 |
H5A—C5—H5B | 108.0 | O22—C24—O23 | 127.0 (3) |
H5A—C5—C6 | 109.3 | O22—C24—C25 | 115.5 (3) |
H5B—C5—C6 | 109.3 | O23—C24—C25 | 117.5 (3) |
N1—C6—C5 | 111.1 (3) | C24—C25—H25 | 108.5 |
N1—C6—H6A | 109.4 | C24—C25—O26 | 109.5 (2) |
N1—C6—H6B | 109.4 | C24—C25—C27 | 110.8 (2) |
C5—C6—H6A | 109.4 | H25—C25—O26 | 108.5 |
C5—C6—H6B | 109.4 | H25—C25—C27 | 108.5 |
H6A—C6—H6B | 108.0 | O26—C25—C27 | 110.9 (3) |
C3—O7—C8 | 114.6 (3) | C25—O26—H26 | 109.5 |
O7—C8—H8A | 109.5 | C25—C27—H27 | 108.3 |
O7—C8—H8B | 109.5 | C25—C27—O28 | 108.9 (3) |
O7—C8—H8C | 109.5 | C25—C27—C29 | 109.1 (2) |
H8A—C8—H8B | 109.5 | H27—C27—O28 | 108.3 |
H8A—C8—H8C | 109.5 | H27—C27—C29 | 108.3 |
H8B—C8—H8C | 109.5 | O28—C27—C29 | 113.8 (2) |
C4—N9—H9 | 117.3 | C27—O28—H28 | 109.5 |
C4—N9—C10 | 125.4 (2) | C27—C29—O30 | 114.3 (2) |
H9—N9—C10 | 117.3 | C27—C29—O31 | 120.0 (3) |
N9—C10—O11 | 122.0 (3) | O30—C29—O31 | 125.7 (3) |
N9—C10—C12 | 118.0 (2) | C29—O30—H30 | 109.5 |
O11—C10—C12 | 120.0 (2) | H32A—O32—H32B | 107.7 |
C10—C12—C13 | 126.5 (2) | ||
H1A—N1—C2—H2A | 176.9 | H9—N9—C10—O11 | −175.6 |
H1A—N1—C2—H2B | 58.2 | H9—N9—C10—C12 | 4.4 |
H1A—N1—C2—C3 | −62.5 | N9—C10—C12—C13 | 12.0 (4) |
H1B—N1—C2—H2A | 59.2 | N9—C10—C12—C17 | −169.8 (3) |
H1B—N1—C2—H2B | −59.4 | O11—C10—C12—C13 | −168.0 (3) |
H1B—N1—C2—C3 | 179.9 | O11—C10—C12—C17 | 10.2 (4) |
C6—N1—C2—H2A | −62.0 | C10—C12—C13—C14 | 177.6 (3) |
C6—N1—C2—H2B | 179.4 | C10—C12—C13—O18 | −2.3 (4) |
C6—N1—C2—C3 | 58.7 (3) | C17—C12—C13—C14 | −0.6 (4) |
H1A—N1—C6—C5 | 64.9 | C17—C12—C13—O18 | 179.5 (3) |
H1A—N1—C6—H6A | −56.0 | C10—C12—C17—C16 | −176.6 (3) |
H1A—N1—C6—H6B | −174.1 | C10—C12—C17—H17 | 3.3 |
H1B—N1—C6—C5 | −177.4 | C13—C12—C17—C16 | 1.7 (4) |
H1B—N1—C6—H6A | 61.7 | C13—C12—C17—H17 | −178.3 |
H1B—N1—C6—H6B | −56.5 | C12—C13—C14—H14 | 179.4 |
C2—N1—C6—C5 | −56.3 (3) | C12—C13—C14—C15 | −0.6 (5) |
C2—N1—C6—H6A | −177.2 | O18—C13—C14—H14 | −0.7 |
C2—N1—C6—H6B | 64.7 | O18—C13—C14—C15 | 179.3 (3) |
N1—C2—C3—H3 | −179.1 | C12—C13—O18—C19 | −179.8 (3) |
N1—C2—C3—C4 | −57.7 (3) | C14—C13—O18—C19 | 0.3 (5) |
N1—C2—C3—O7 | 59.5 (3) | C13—C14—C15—C16 | 0.7 (5) |
H2A—C2—C3—H3 | −58.5 | C13—C14—C15—N20 | −179.9 (3) |
H2A—C2—C3—C4 | 62.9 | H14—C14—C15—C16 | −179.3 |
H2A—C2—C3—O7 | −179.9 | H14—C14—C15—N20 | 0.1 |
H2B—C2—C3—H3 | 60.2 | C14—C15—C16—C17 | 0.4 (5) |
H2B—C2—C3—C4 | −178.4 | C14—C15—C16—Cl21 | 178.9 (3) |
H2B—C2—C3—O7 | −61.2 | N20—C15—C16—C17 | −179.0 (3) |
C2—C3—C4—H4 | −64.3 | N20—C15—C16—Cl21 | −0.5 (4) |
C2—C3—C4—C5 | 55.5 (3) | C14—C15—N20—H20A | 0.0 |
C2—C3—C4—N9 | 177.6 (3) | C14—C15—N20—H20B | 180.0 |
H3—C3—C4—H4 | 57.1 | C16—C15—N20—H20A | 179.4 |
H3—C3—C4—C5 | 176.9 | C16—C15—N20—H20B | −0.6 |
H3—C3—C4—N9 | −61.0 | C15—C16—C17—C12 | −1.6 (5) |
O7—C3—C4—H4 | 175.5 | C15—C16—C17—H17 | 178.4 |
O7—C3—C4—C5 | −64.7 (3) | Cl21—C16—C17—C12 | 179.9 (2) |
O7—C3—C4—N9 | 57.4 (3) | Cl21—C16—C17—H17 | −0.2 |
C2—C3—O7—C8 | 77.3 (4) | C13—O18—C19—H19A | 176.4 |
H3—C3—O7—C8 | −44.1 | C13—O18—C19—H19B | 56.4 |
C4—C3—O7—C8 | −162.6 (3) | C13—O18—C19—H19C | −63.6 |
C3—C4—C5—H5A | −173.9 | O22—C24—C25—H25 | 115.9 |
C3—C4—C5—H5B | 68.1 | O22—C24—C25—O26 | −2.4 (4) |
C3—C4—C5—C6 | −52.9 (3) | O22—C24—C25—C27 | −125.1 (3) |
H4—C4—C5—H5A | −54.1 | O23—C24—C25—H25 | −62.9 |
H4—C4—C5—H5B | −172.1 | O23—C24—C25—O26 | 178.8 (3) |
H4—C4—C5—C6 | 66.9 | O23—C24—C25—C27 | 56.1 (4) |
N9—C4—C5—H5A | 65.8 | C24—C25—O26—H26 | 2.6 |
N9—C4—C5—H5B | −52.1 | H25—C25—O26—H26 | −115.7 |
N9—C4—C5—C6 | −173.1 (3) | C27—C25—O26—H26 | 125.3 |
C3—C4—N9—H9 | −36.7 | C24—C25—C27—H27 | −56.2 |
C3—C4—N9—C10 | 143.3 (3) | C24—C25—C27—O28 | 61.4 (3) |
H4—C4—N9—H9 | −154.7 | C24—C25—C27—C29 | −173.9 (3) |
H4—C4—N9—C10 | 25.3 | H25—C25—C27—H27 | 62.8 |
C5—C4—N9—H9 | 85.3 | H25—C25—C27—O28 | −179.6 |
C5—C4—N9—C10 | −94.7 (3) | H25—C25—C27—C29 | −54.9 |
C4—C5—C6—N1 | 53.0 (3) | O26—C25—C27—H27 | −178.1 |
C4—C5—C6—H6A | 173.9 | O26—C25—C27—O28 | −60.5 (3) |
C4—C5—C6—H6B | −67.9 | O26—C25—C27—C29 | 64.2 (3) |
H5A—C5—C6—N1 | 174.0 | C25—C27—O28—H28 | −164.0 |
H5A—C5—C6—H6A | −65.1 | H27—C27—O28—H28 | −46.4 |
H5A—C5—C6—H6B | 53.1 | C29—C27—O28—H28 | 74.2 |
H5B—C5—C6—N1 | −68.0 | C25—C27—C29—O30 | −125.1 (3) |
H5B—C5—C6—H6A | 52.9 | C25—C27—C29—O31 | 55.8 (4) |
H5B—C5—C6—H6B | 171.0 | H27—C27—C29—O30 | 117.2 |
C3—O7—C8—H8A | −178.4 | H27—C27—C29—O31 | −61.9 |
C3—O7—C8—H8B | 61.6 | O28—C27—C29—O30 | −3.3 (4) |
C3—O7—C8—H8C | −58.4 | O28—C27—C29—O31 | 177.6 (3) |
C4—N9—C10—O11 | 4.3 (5) | C27—C29—O30—H30 | −176.7 |
C4—N9—C10—C12 | −175.6 (3) | O31—C29—O30—H30 | 2.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9···O18 | 0.86 | 1.97 | 2.643 (3) | 134 |
O26—H26···O22 | 0.82 | 2.03 | 2.545 (4) | 120 |
O28—H28···O11 | 0.82 | 1.97 | 2.776 (3) | 167 |
O32—H32A···O26 | 0.85 | 1.96 | 2.764 (5) | 158 |
N1—H1A···O11i | 0.90 | 2.21 | 2.953 (3) | 140 |
N1—H1B···O22ii | 0.90 | 1.86 | 2.728 (4) | 161 |
N20—H20A···O23iii | 0.86 | 2.16 | 2.955 (4) | 155 |
N20—H20B···O31iv | 0.86 | 2.41 | 2.970 (4) | 123 |
O30—H30···O23v | 0.82 | 1.72 | 2.535 (3) | 171 |
O32—H32B···O28vi | 0.85 | 2.34 | 3.107 (5) | 150 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y+1/2, −z+1; (iii) −x+1, y+1/2, −z+2; (iv) −x, y+1/2, −z+2; (v) x−1, y, z; (vi) −x+1, y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H21ClN3O3+·C4H5O6−·H2O |
Mr | 481.89 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 7.6086 (4), 10.664 (1), 14.0482 (6) |
β (°) | 93.980 (6) |
V (Å3) | 1137.1 (1) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 2.01 |
Crystal size (mm) | 0.45 × 0.30 × 0.26 |
Data collection | |
Diffractometer | Siemens P4 four-circle diffractometer |
Absorption correction | ψ scan (XEMP; Siemens, 1989) |
Tmin, Tmax | 0.325, 0.593 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 2935, 2350, 2280 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.107, 1.06 |
No. of reflections | 2350 |
No. of parameters | 295 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.26 |
Absolute structure | Flack (1983), 220 Friedel pairs |
Absolute structure parameter | −0.01 (2) |
Computer programs: XSCANS (Siemens, 1996), XSCANS, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), DIAMOND (Bergerhoff, 1996), PARST (Nardelli, 1983), PLATON (Spek, 1998) and WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9···O18 | 0.86 | 1.97 | 2.643 (3) | 134 |
O26—H26···O22 | 0.82 | 2.03 | 2.545 (4) | 120 |
O28—H28···O11 | 0.82 | 1.97 | 2.776 (3) | 167 |
O32—H32A···O26 | 0.85 | 1.96 | 2.764 (5) | 158 |
N1—H1A···O11i | 0.90 | 2.21 | 2.953 (3) | 140 |
N1—H1B···O22ii | 0.90 | 1.86 | 2.728 (4) | 161 |
N20—H20A···O23iii | 0.86 | 2.16 | 2.955 (4) | 155 |
N20—H20B···O31iv | 0.86 | 2.41 | 2.970 (4) | 123 |
O30—H30···O23v | 0.82 | 1.72 | 2.535 (3) | 171 |
O32—H32B···O28vi | 0.85 | 2.34 | 3.107 (5) | 150 |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y+1/2, −z+1; (iii) −x+1, y+1/2, −z+2; (iv) −x, y+1/2, −z+2; (v) x−1, y, z; (vi) −x+1, y−1/2, −z+1. |
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The title compound, (I), is the (+)-tartrate salt of the (+)-enantiomer of norcisapride.
Racemic norcisapride is the principal metabolite of racemic cisapride, a widely used gastrokinetic drug (Meuldermans et al., 1988). The metabolization occurs mainly via the cytochrome P-450 isoenzyme CYP3A4 (Bohets et al., 2000). Certain therapeutic agents (e.g. ketoconazole) that inhibit the metabolic pathway of cisapride can give rise to undesirably high cisapride blood levels that may cause side effects.
It has been discovered that (-)-norcisapride is a potent drug for the treatment of gastro-esophageal reflux disease while substantially reducing adverse effects associated with the administration of racemic cisapride (McCullough & Aberg, 1998). It has also been found that (+)-norcisapride has both 5-HT3 antagonistic and 5-HT4 agonistic properties and is further substantially devoid of central nervous system effects (Heykants et al., 1999).
To contribute to a better understanding of the mechanism of action of the (-)- and (+)-norcisapride, the crystal structure and absolute configuration of the title compound was determined.
The absolute configuration of the (+)-norcisapride moiety is 3S,4R in view of the fact that the Flack (1983) parameter for this configuration is −0.01 (2) and that the known configuration 2R,3R for (+)-tartrate is obtained. As in the structures of cisapride (Collin et al., 1989) and cisapride tartrate (Peeters et al., 1997) an intramolecular hydrogen bond between the amidic N atom and the O atom of the o-methoxy substituent (Table 1) forces the amido moiety and the substituted benzene ring to be roughly coplanar [dihedral angle between the two least-squares planes: 10.8 (1)°]. The C atom chain of the hydrogen tartrate ion is in an extended conformation with the hydroxyl O atoms -sc with respect to one another. The hydrogen bonds listed in Table 2 form a three-dimensional network in the crystal.