Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047368/cv2304sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047368/cv2304Isup2.hkl |
CCDC reference: 667264
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.084
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc. PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 120.00 A 3
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O5 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 12
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 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 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related crystal structures, see: Su & Zhu (2004); Sun et al. (2007). For biological activities of tegaserod maleate, see: Satish et al. (2001); Tack et al. (2001). Schikowski et al. (2002); Kamm et al. (2005).
To a solution of tegaserod (9.2 mmol) in 40 ml of anhydrous ethanol a solution of maleate(10 mmol) in 10 ml of anhydrous ethanol was added in 5 min at room temperature. The mixture was stirred for 1 h. The solvent was then evaporated and washed with anhydrous ethanol. The crude product was recrystallized from anhydrous ethanol to afford the desired product as colourless solid (m.p. 462 K). Single crystal of (I) were obtained by slow evaporation of aqueous ethanol(95%) solution at ambient temperature after 12 d.
All hydrogen atoms were geometrically fixed at calculated positions (C—H 0.93–0.97 Å, N—H 0.86 Å, O—H 0.82 Å), and refined as riding with Uiso(H) = 1.2–1.5 Ueq(parent atom). The crystal packing contains the voids of 120 Å3 centered at (0, 0.37, 1/4) and equivalent positions. Because of weak process of crystallization, all obtained single-crystals were of poor quality resulting in poor ratio observed/unique reflections of 0.35.
Tegaserod maleate is effective in the initial and retreatment of irritable bowel syndrome(IBS) and gastroesophageal reflux disease (GERO) as 5-HT4 receptor agonist (Satish et al., 2001; Schikowski et al., 2002). The study about tegaserod salts concentrates mainly in the clinical practice (Tack et al., 2001; Kamm et al., 2005), while structural studies of them have been rarely reported (Su & Zhu, 2004). As a part of our investigation on tegaserod salts, we present here the structure of the title compound, (I) (Fig. 1).
In (I), the guanidyl group is protonated. The C—N bond lengths in the guanidyl group show that the C—N bonds are conjugated, providing the planarity of guanidyl group. Similar result has been observed in other complex containing this group (Sun et al., 2007).
A number of intermolecular N—H···O hydrogen bonds (Table 1) stabilize the crystal packing.
For related crystal structures, see: Su & Zhu (2004); Sun et al. (2007). For biological activities of tegaserod maleate, see: Satish et al. (2001); Tack et al. (2001). Schikowski et al. (2002); Kamm et al. (2005).
Data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
Fig. 1. The molecular structure of (I) showing atomic numbering. Displacement ellipsoids are drawn at the 30% probability level. |
C16H24N5O+·C4H3O4− | F(000) = 1776 |
Mr = 417.47 | Dx = 1.180 Mg m−3 |
Monoclinic, C2/c | Melting point: 462 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 24.873 (3) Å | Cell parameters from 919 reflections |
b = 8.4962 (16) Å | θ = 2.4–18.6° |
c = 22.294 (2) Å | µ = 0.09 mm−1 |
β = 93.732 (2)° | T = 298 K |
V = 4701.3 (11) Å3 | Plate, white |
Z = 8 | 0.55 × 0.42 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 4110 independent reflections |
Radiation source: fine-focus sealed tube | 1423 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −29→29 |
Tmin = 0.954, Tmax = 0.985 | k = −9→9 |
9394 measured reflections | l = −12→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0053P)2] where P = (Fo2 + 2Fc2)/3 |
4110 reflections | (Δ/σ)max < 0.001 |
273 parameters | Δρmax = 0.14 e Å−3 |
12 restraints | Δρmin = −0.12 e Å−3 |
C16H24N5O+·C4H3O4− | V = 4701.3 (11) Å3 |
Mr = 417.47 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 24.873 (3) Å | µ = 0.09 mm−1 |
b = 8.4962 (16) Å | T = 298 K |
c = 22.294 (2) Å | 0.55 × 0.42 × 0.18 mm |
β = 93.732 (2)° |
Bruker SMART CCD area-detector diffractometer | 4110 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1423 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.985 | Rint = 0.058 |
9394 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 12 restraints |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.14 e Å−3 |
4110 reflections | Δρmin = −0.12 e Å−3 |
273 parameters |
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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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 | ||
N1 | 0.18528 (10) | 0.3231 (4) | 0.26144 (12) | 0.0815 (9) | |
H1 | 0.1625 | 0.3205 | 0.2308 | 0.098* | |
N2 | 0.31664 (11) | 0.4735 (3) | 0.40465 (12) | 0.0720 (8) | |
N3 | 0.35352 (11) | 0.5854 (3) | 0.42702 (12) | 0.0842 (9) | |
H3 | 0.3558 | 0.6767 | 0.4107 | 0.101* | |
N4 | 0.37930 (10) | 0.4053 (4) | 0.50059 (12) | 0.0812 (9) | |
H4 | 0.3547 | 0.3445 | 0.4846 | 0.097* | |
N5 | 0.42242 (10) | 0.6447 (3) | 0.49566 (10) | 0.0934 (10) | |
H5A | 0.4434 | 0.6202 | 0.5264 | 0.112* | |
H5B | 0.4257 | 0.7345 | 0.4785 | 0.112* | |
O1 | 0.57296 (9) | 1.0683 (3) | 0.57298 (9) | 0.0937 (8) | |
O2 | 0.63215 (9) | 1.1500 (3) | 0.64577 (9) | 0.0990 (9) | |
O3 | 0.51639 (8) | 0.8387 (3) | 0.55244 (9) | 0.0880 (8) | |
H3A | 0.5364 | 0.9147 | 0.5576 | 0.132* | |
O4 | 0.50672 (10) | 0.6058 (3) | 0.59162 (11) | 0.1094 (10) | |
O5 | 0.24227 (10) | −0.1033 (3) | 0.43832 (12) | 0.1085 (9) | |
C1 | 0.60303 (14) | 1.0445 (5) | 0.62047 (16) | 0.0758 (11) | |
C2 | 0.60531 (14) | 0.8864 (5) | 0.64804 (14) | 0.0783 (11) | |
H2 | 0.6320 | 0.8736 | 0.6789 | 0.094* | |
C3 | 0.57583 (14) | 0.7612 (5) | 0.63601 (15) | 0.0853 (12) | |
H3B | 0.5854 | 0.6755 | 0.6603 | 0.102* | |
C4 | 0.53053 (16) | 0.7283 (5) | 0.59181 (18) | 0.0809 (12) | |
C5 | 0.21768 (13) | 0.4462 (4) | 0.27763 (15) | 0.0801 (10) | |
H5 | 0.2187 | 0.5411 | 0.2570 | 0.096* | |
C6 | 0.24901 (13) | 0.4099 (5) | 0.32940 (14) | 0.0663 (10) | |
C7 | 0.23417 (13) | 0.2540 (4) | 0.34535 (15) | 0.0621 (10) | |
C8 | 0.19506 (14) | 0.2007 (5) | 0.30291 (15) | 0.0685 (10) | |
C9 | 0.17191 (14) | 0.0541 (5) | 0.30518 (17) | 0.0864 (12) | |
H9 | 0.1454 | 0.0217 | 0.2765 | 0.104* | |
C10 | 0.18961 (14) | −0.0418 (5) | 0.35149 (18) | 0.0922 (12) | |
H10 | 0.1753 | −0.1425 | 0.3540 | 0.111* | |
C11 | 0.22844 (15) | 0.0072 (5) | 0.39489 (17) | 0.0801 (12) | |
C12 | 0.25123 (12) | 0.1520 (5) | 0.39251 (14) | 0.0670 (10) | |
H12 | 0.2776 | 0.1831 | 0.4215 | 0.080* | |
C13 | 0.28742 (13) | 0.5141 (4) | 0.35782 (15) | 0.0769 (11) | |
H13 | 0.2914 | 0.6144 | 0.3420 | 0.092* | |
C14 | 0.38510 (15) | 0.5443 (5) | 0.47484 (17) | 0.0736 (11) | |
C15 | 0.41036 (12) | 0.3455 (4) | 0.55299 (13) | 0.0786 (10) | |
H15A | 0.4057 | 0.4135 | 0.5872 | 0.094* | |
H15B | 0.4483 | 0.3435 | 0.5455 | 0.094* | |
C16 | 0.39137 (12) | 0.1818 (4) | 0.56628 (13) | 0.0759 (10) | |
H16A | 0.3963 | 0.1153 | 0.5317 | 0.091* | |
H16B | 0.3531 | 0.1851 | 0.5725 | 0.091* | |
C17 | 0.42096 (12) | 0.1093 (4) | 0.62119 (14) | 0.0813 (11) | |
H17A | 0.4592 | 0.1057 | 0.6151 | 0.098* | |
H17B | 0.4160 | 0.1754 | 0.6559 | 0.098* | |
C18 | 0.40137 (13) | −0.0553 (5) | 0.63385 (15) | 0.0973 (12) | |
H18A | 0.4080 | −0.1226 | 0.6000 | 0.117* | |
H18B | 0.3628 | −0.0525 | 0.6380 | 0.117* | |
C19 | 0.42889 (14) | −0.1251 (4) | 0.69043 (15) | 0.1351 (16) | |
H19A | 0.4671 | −0.1275 | 0.6867 | 0.203* | |
H19B | 0.4159 | −0.2302 | 0.6960 | 0.203* | |
H19C | 0.4211 | −0.0617 | 0.7244 | 0.203* | |
C20 | 0.28068 (13) | −0.0593 (4) | 0.48471 (15) | 0.1021 (13) | |
H20A | 0.3133 | −0.0271 | 0.4675 | 0.153* | |
H20B | 0.2880 | −0.1473 | 0.5110 | 0.153* | |
H20C | 0.2668 | 0.0264 | 0.5071 | 0.153* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.066 (2) | 0.108 (3) | 0.0679 (19) | −0.0014 (18) | −0.0122 (16) | −0.0043 (18) |
N2 | 0.075 (2) | 0.072 (2) | 0.0670 (19) | −0.0053 (18) | −0.0096 (17) | 0.0091 (18) |
N3 | 0.098 (2) | 0.070 (2) | 0.081 (2) | −0.014 (2) | −0.0259 (18) | 0.0077 (18) |
N4 | 0.098 (2) | 0.073 (3) | 0.070 (2) | −0.022 (2) | −0.0145 (18) | 0.0087 (18) |
N5 | 0.120 (2) | 0.080 (2) | 0.078 (2) | −0.024 (2) | −0.0150 (18) | 0.0037 (18) |
O1 | 0.1099 (19) | 0.096 (2) | 0.0706 (15) | −0.0253 (16) | −0.0285 (14) | 0.0151 (14) |
O2 | 0.113 (2) | 0.095 (2) | 0.0846 (17) | −0.0356 (16) | −0.0278 (15) | 0.0050 (16) |
O3 | 0.0922 (18) | 0.098 (2) | 0.0719 (16) | −0.0168 (16) | −0.0102 (14) | −0.0025 (15) |
O4 | 0.122 (2) | 0.087 (2) | 0.116 (2) | −0.0410 (18) | −0.0185 (17) | −0.0034 (18) |
O5 | 0.115 (2) | 0.092 (2) | 0.114 (2) | −0.0311 (18) | −0.0276 (18) | 0.0317 (19) |
C1 | 0.073 (3) | 0.090 (4) | 0.064 (3) | −0.015 (3) | 0.005 (2) | 0.003 (3) |
C2 | 0.086 (3) | 0.087 (3) | 0.059 (2) | −0.009 (3) | −0.017 (2) | 0.008 (2) |
C3 | 0.090 (3) | 0.085 (3) | 0.078 (3) | −0.007 (3) | −0.018 (2) | 0.009 (2) |
C4 | 0.082 (3) | 0.088 (4) | 0.072 (3) | −0.009 (3) | 0.000 (3) | −0.009 (3) |
C5 | 0.074 (3) | 0.098 (3) | 0.067 (2) | 0.000 (2) | 0.0006 (17) | 0.012 (2) |
C6 | 0.061 (2) | 0.081 (3) | 0.055 (2) | −0.011 (2) | −0.0014 (16) | 0.008 (2) |
C7 | 0.049 (2) | 0.074 (3) | 0.064 (2) | −0.001 (2) | 0.005 (2) | 0.003 (2) |
C8 | 0.054 (2) | 0.090 (3) | 0.061 (2) | −0.001 (2) | 0.000 (2) | −0.005 (2) |
C9 | 0.071 (3) | 0.103 (4) | 0.084 (3) | −0.016 (3) | −0.011 (2) | −0.010 (3) |
C10 | 0.078 (3) | 0.088 (3) | 0.109 (3) | −0.026 (3) | −0.005 (3) | −0.008 (3) |
C11 | 0.074 (3) | 0.081 (4) | 0.084 (3) | −0.021 (3) | −0.004 (2) | 0.007 (3) |
C12 | 0.057 (2) | 0.082 (3) | 0.061 (2) | −0.007 (2) | −0.0043 (19) | 0.002 (2) |
C13 | 0.076 (3) | 0.079 (3) | 0.074 (2) | −0.009 (2) | −0.0054 (19) | 0.018 (2) |
C14 | 0.077 (3) | 0.077 (3) | 0.065 (3) | −0.016 (3) | −0.008 (2) | −0.010 (3) |
C15 | 0.090 (3) | 0.087 (3) | 0.056 (2) | −0.001 (2) | −0.013 (2) | 0.004 (2) |
C16 | 0.077 (2) | 0.085 (3) | 0.066 (2) | −0.005 (2) | 0.008 (2) | 0.003 (2) |
C17 | 0.087 (3) | 0.094 (3) | 0.062 (2) | 0.016 (2) | 0.003 (2) | 0.007 (2) |
C18 | 0.096 (3) | 0.107 (4) | 0.090 (3) | 0.011 (3) | 0.017 (2) | 0.024 (3) |
C19 | 0.144 (4) | 0.158 (4) | 0.104 (3) | 0.032 (3) | 0.010 (3) | 0.043 (3) |
C20 | 0.106 (3) | 0.105 (3) | 0.094 (3) | −0.012 (3) | −0.004 (3) | 0.037 (3) |
N1—C5 | 1.355 (4) | C7—C8 | 1.388 (4) |
N1—C8 | 1.402 (4) | C7—C12 | 1.407 (4) |
N1—H1 | 0.8600 | C8—C9 | 1.374 (4) |
N2—C13 | 1.280 (3) | C9—C10 | 1.365 (4) |
N2—N3 | 1.391 (3) | C9—H9 | 0.9300 |
N3—C14 | 1.329 (4) | C10—C11 | 1.386 (4) |
N3—H3 | 0.8600 | C10—H10 | 0.9300 |
N4—C14 | 1.325 (4) | C11—C12 | 1.356 (4) |
N4—C15 | 1.450 (3) | C12—H12 | 0.9300 |
N4—H4 | 0.8600 | C13—H13 | 0.9300 |
N5—C14 | 1.322 (4) | C15—C16 | 1.504 (4) |
N5—H5A | 0.8600 | C15—H15A | 0.9700 |
N5—H5B | 0.8600 | C15—H15B | 0.9700 |
O1—C1 | 1.272 (3) | C16—C17 | 1.518 (3) |
O2—C1 | 1.262 (4) | C16—H16A | 0.9700 |
O3—C4 | 1.316 (4) | C16—H16B | 0.9700 |
O3—H3A | 0.8200 | C17—C18 | 1.513 (4) |
O4—C4 | 1.198 (4) | C17—H17A | 0.9700 |
O5—C11 | 1.376 (4) | C17—H17B | 0.9700 |
O5—C20 | 1.412 (3) | C18—C19 | 1.516 (4) |
C1—C2 | 1.477 (4) | C18—H18A | 0.9700 |
C2—C3 | 1.309 (4) | C18—H18B | 0.9700 |
C2—H2 | 0.9300 | C19—H19A | 0.9600 |
C3—C4 | 1.475 (4) | C19—H19B | 0.9600 |
C3—H3B | 0.9300 | C19—H19C | 0.9600 |
C5—C6 | 1.385 (4) | C20—H20A | 0.9600 |
C5—H5 | 0.9300 | C20—H20B | 0.9600 |
C6—C13 | 1.421 (4) | C20—H20C | 0.9600 |
C6—C7 | 1.426 (4) | ||
C5—N1—C8 | 108.8 (3) | O5—C11—C10 | 114.6 (4) |
C5—N1—H1 | 125.6 | C11—C12—C7 | 118.8 (3) |
C8—N1—H1 | 125.6 | C11—C12—H12 | 120.6 |
C13—N2—N3 | 115.8 (3) | C7—C12—H12 | 120.6 |
C14—N3—N2 | 116.7 (3) | N2—C13—C6 | 121.7 (3) |
C14—N3—H3 | 121.6 | N2—C13—H13 | 119.2 |
N2—N3—H3 | 121.6 | C6—C13—H13 | 119.2 |
C14—N4—C15 | 126.4 (3) | N5—C14—N4 | 121.1 (4) |
C14—N4—H4 | 116.8 | N5—C14—N3 | 118.5 (4) |
C15—N4—H4 | 116.8 | N4—C14—N3 | 120.4 (4) |
C14—N5—H5A | 120.0 | N4—C15—C16 | 109.0 (3) |
C14—N5—H5B | 120.0 | N4—C15—H15A | 109.9 |
H5A—N5—H5B | 120.0 | C16—C15—H15A | 109.9 |
C4—O3—H3A | 109.5 | N4—C15—H15B | 109.9 |
C11—O5—C20 | 117.4 (3) | C16—C15—H15B | 109.9 |
O2—C1—O1 | 123.2 (4) | H15A—C15—H15B | 108.3 |
O2—C1—C2 | 117.0 (4) | C15—C16—C17 | 113.1 (3) |
O1—C1—C2 | 119.7 (4) | C15—C16—H16A | 109.0 |
C3—C2—C1 | 130.4 (4) | C17—C16—H16A | 109.0 |
C3—C2—H2 | 114.8 | C15—C16—H16B | 109.0 |
C1—C2—H2 | 114.8 | C17—C16—H16B | 109.0 |
C2—C3—C4 | 133.2 (4) | H16A—C16—H16B | 107.8 |
C2—C3—H3B | 113.4 | C18—C17—C16 | 112.4 (3) |
C4—C3—H3B | 113.4 | C18—C17—H17A | 109.1 |
O4—C4—O3 | 120.4 (4) | C16—C17—H17A | 109.1 |
O4—C4—C3 | 121.6 (4) | C18—C17—H17B | 109.1 |
O3—C4—C3 | 118.0 (4) | C16—C17—H17B | 109.1 |
N1—C5—C6 | 110.1 (3) | H17A—C17—H17B | 107.9 |
N1—C5—H5 | 125.0 | C17—C18—C19 | 112.5 (3) |
C6—C5—H5 | 125.0 | C17—C18—H18A | 109.1 |
C5—C6—C13 | 124.0 (4) | C19—C18—H18A | 109.1 |
C5—C6—C7 | 105.9 (3) | C17—C18—H18B | 109.1 |
C13—C6—C7 | 130.2 (3) | C19—C18—H18B | 109.1 |
C8—C7—C12 | 118.2 (4) | H18A—C18—H18B | 107.8 |
C8—C7—C6 | 108.3 (4) | C18—C19—H19A | 109.5 |
C12—C7—C6 | 133.5 (4) | C18—C19—H19B | 109.5 |
C9—C8—C7 | 123.2 (4) | H19A—C19—H19B | 109.5 |
C9—C8—N1 | 129.9 (4) | C18—C19—H19C | 109.5 |
C7—C8—N1 | 106.9 (4) | H19A—C19—H19C | 109.5 |
C10—C9—C8 | 117.0 (4) | H19B—C19—H19C | 109.5 |
C10—C9—H9 | 121.5 | O5—C20—H20A | 109.5 |
C8—C9—H9 | 121.5 | O5—C20—H20B | 109.5 |
C9—C10—C11 | 121.6 (4) | H20A—C20—H20B | 109.5 |
C9—C10—H10 | 119.2 | O5—C20—H20C | 109.5 |
C11—C10—H10 | 119.2 | H20A—C20—H20C | 109.5 |
C12—C11—O5 | 124.1 (4) | H20B—C20—H20C | 109.5 |
C12—C11—C10 | 121.3 (4) | ||
C13—N2—N3—C14 | −178.5 (3) | C8—C9—C10—C11 | 1.1 (5) |
O2—C1—C2—C3 | 171.5 (4) | C20—O5—C11—C12 | 3.3 (5) |
O1—C1—C2—C3 | −9.2 (6) | C20—O5—C11—C10 | −178.5 (3) |
C1—C2—C3—C4 | 0.3 (7) | C9—C10—C11—C12 | −1.2 (6) |
C2—C3—C4—O4 | −174.7 (4) | C9—C10—C11—O5 | −179.5 (3) |
C2—C3—C4—O3 | 4.7 (6) | O5—C11—C12—C7 | 179.1 (3) |
C8—N1—C5—C6 | −0.3 (4) | C10—C11—C12—C7 | 1.0 (5) |
N1—C5—C6—C13 | 179.7 (3) | C8—C7—C12—C11 | −0.7 (5) |
N1—C5—C6—C7 | −0.1 (4) | C6—C7—C12—C11 | −180.0 (3) |
C5—C6—C7—C8 | 0.5 (3) | N3—N2—C13—C6 | 178.5 (3) |
C13—C6—C7—C8 | −179.3 (3) | C5—C6—C13—N2 | −177.9 (3) |
C5—C6—C7—C12 | 179.8 (3) | C7—C6—C13—N2 | 1.9 (5) |
C13—C6—C7—C12 | 0.0 (6) | C15—N4—C14—N5 | 1.0 (5) |
C12—C7—C8—C9 | 0.7 (5) | C15—N4—C14—N3 | −179.4 (3) |
C6—C7—C8—C9 | −179.9 (3) | N2—N3—C14—N5 | 176.8 (3) |
C12—C7—C8—N1 | 179.9 (3) | N2—N3—C14—N4 | −2.8 (5) |
C6—C7—C8—N1 | −0.7 (4) | C14—N4—C15—C16 | −178.8 (3) |
C5—N1—C8—C9 | 179.7 (3) | N4—C15—C16—C17 | −179.1 (2) |
C5—N1—C8—C7 | 0.6 (4) | C15—C16—C17—C18 | −180.0 (3) |
C7—C8—C9—C10 | −0.9 (5) | C16—C17—C18—C19 | −177.2 (3) |
N1—C8—C9—C10 | −179.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.01 | 2.829 (3) | 159 |
N3—H3···O2ii | 0.86 | 1.97 | 2.809 (3) | 164 |
N5—H5B···O1ii | 0.86 | 2.03 | 2.885 (3) | 171 |
N5—H5A···O4 | 0.86 | 2.08 | 2.915 (4) | 165 |
O3—H3A···O1 | 0.82 | 1.61 | 2.432 (3) | 175 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H24N5O+·C4H3O4− |
Mr | 417.47 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 24.873 (3), 8.4962 (16), 22.294 (2) |
β (°) | 93.732 (2) |
V (Å3) | 4701.3 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.55 × 0.42 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.954, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9394, 4110, 1423 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.084, 1.00 |
No. of reflections | 4110 |
No. of parameters | 273 |
No. of restraints | 12 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.12 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.01 | 2.829 (3) | 159.1 |
N3—H3···O2ii | 0.86 | 1.97 | 2.809 (3) | 163.7 |
N5—H5B···O1ii | 0.86 | 2.03 | 2.885 (3) | 171.3 |
N5—H5A···O4 | 0.86 | 2.08 | 2.915 (4) | 165.1 |
O3—H3A···O1 | 0.82 | 1.61 | 2.432 (3) | 174.9 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x+1, −y+2, −z+1. |
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Tegaserod maleate is effective in the initial and retreatment of irritable bowel syndrome(IBS) and gastroesophageal reflux disease (GERO) as 5-HT4 receptor agonist (Satish et al., 2001; Schikowski et al., 2002). The study about tegaserod salts concentrates mainly in the clinical practice (Tack et al., 2001; Kamm et al., 2005), while structural studies of them have been rarely reported (Su & Zhu, 2004). As a part of our investigation on tegaserod salts, we present here the structure of the title compound, (I) (Fig. 1).
In (I), the guanidyl group is protonated. The C—N bond lengths in the guanidyl group show that the C—N bonds are conjugated, providing the planarity of guanidyl group. Similar result has been observed in other complex containing this group (Sun et al., 2007).
A number of intermolecular N—H···O hydrogen bonds (Table 1) stabilize the crystal packing.