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The title compound, [(5-methoxy­indol-3-yl)methyl­ene­hydrazino]­(pentyl­amino)methaniminium maleate, C16H24N5O+·C4H3O4, was synthesized by the reaction of tegaserod and maleic acid in anhydrous ethanol. In the tegaserod cation, the guanidyl group is protonated. A number of inter­molecular N—H...O hydrogen bonds stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047368/cv2304sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047368/cv2304Isup2.hkl
Contains datablock I

CCDC reference: 667264

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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.

Related literature top

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).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing atomic numbering. Displacement ellipsoids are drawn at the 30% probability level.
[(5-methoxyindol-3-yl)methylenehydrazino](pentylamino)methaniminium maleate top
Crystal data top
C16H24N5O+·C4H3O4F(000) = 1776
Mr = 417.47Dx = 1.180 Mg m3
Monoclinic, C2/cMelting point: 462 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 24.873 (3) ÅCell parameters from 919 reflections
b = 8.4962 (16) Åθ = 2.4–18.6°
c = 22.294 (2) ŵ = 0.09 mm1
β = 93.732 (2)°T = 298 K
V = 4701.3 (11) Å3Plate, white
Z = 80.55 × 0.42 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4110 independent reflections
Radiation source: fine-focus sealed tube1423 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
φ and ω scansθmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2929
Tmin = 0.954, Tmax = 0.985k = 99
9394 measured reflectionsl = 1226
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H-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 parametersΔρmax = 0.14 e Å3
12 restraintsΔρmin = 0.12 e Å3
Crystal data top
C16H24N5O+·C4H3O4V = 4701.3 (11) Å3
Mr = 417.47Z = 8
Monoclinic, C2/cMo Kα radiation
a = 24.873 (3) ŵ = 0.09 mm1
b = 8.4962 (16) ÅT = 298 K
c = 22.294 (2) Å0.55 × 0.42 × 0.18 mm
β = 93.732 (2)°
Data collection top
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 = 0.985Rint = 0.058
9394 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04912 restraints
wR(F2) = 0.084H-atom parameters constrained
S = 1.00Δρmax = 0.14 e Å3
4110 reflectionsΔρmin = 0.12 e Å3
273 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.18528 (10)0.3231 (4)0.26144 (12)0.0815 (9)
H10.16250.32050.23080.098*
N20.31664 (11)0.4735 (3)0.40465 (12)0.0720 (8)
N30.35352 (11)0.5854 (3)0.42702 (12)0.0842 (9)
H30.35580.67670.41070.101*
N40.37930 (10)0.4053 (4)0.50059 (12)0.0812 (9)
H40.35470.34450.48460.097*
N50.42242 (10)0.6447 (3)0.49566 (10)0.0934 (10)
H5A0.44340.62020.52640.112*
H5B0.42570.73450.47850.112*
O10.57296 (9)1.0683 (3)0.57298 (9)0.0937 (8)
O20.63215 (9)1.1500 (3)0.64577 (9)0.0990 (9)
O30.51639 (8)0.8387 (3)0.55244 (9)0.0880 (8)
H3A0.53640.91470.55760.132*
O40.50672 (10)0.6058 (3)0.59162 (11)0.1094 (10)
O50.24227 (10)0.1033 (3)0.43832 (12)0.1085 (9)
C10.60303 (14)1.0445 (5)0.62047 (16)0.0758 (11)
C20.60531 (14)0.8864 (5)0.64804 (14)0.0783 (11)
H20.63200.87360.67890.094*
C30.57583 (14)0.7612 (5)0.63601 (15)0.0853 (12)
H3B0.58540.67550.66030.102*
C40.53053 (16)0.7283 (5)0.59181 (18)0.0809 (12)
C50.21768 (13)0.4462 (4)0.27763 (15)0.0801 (10)
H50.21870.54110.25700.096*
C60.24901 (13)0.4099 (5)0.32940 (14)0.0663 (10)
C70.23417 (13)0.2540 (4)0.34535 (15)0.0621 (10)
C80.19506 (14)0.2007 (5)0.30291 (15)0.0685 (10)
C90.17191 (14)0.0541 (5)0.30518 (17)0.0864 (12)
H90.14540.02170.27650.104*
C100.18961 (14)0.0418 (5)0.35149 (18)0.0922 (12)
H100.17530.14250.35400.111*
C110.22844 (15)0.0072 (5)0.39489 (17)0.0801 (12)
C120.25123 (12)0.1520 (5)0.39251 (14)0.0670 (10)
H120.27760.18310.42150.080*
C130.28742 (13)0.5141 (4)0.35782 (15)0.0769 (11)
H130.29140.61440.34200.092*
C140.38510 (15)0.5443 (5)0.47484 (17)0.0736 (11)
C150.41036 (12)0.3455 (4)0.55299 (13)0.0786 (10)
H15A0.40570.41350.58720.094*
H15B0.44830.34350.54550.094*
C160.39137 (12)0.1818 (4)0.56628 (13)0.0759 (10)
H16A0.39630.11530.53170.091*
H16B0.35310.18510.57250.091*
C170.42096 (12)0.1093 (4)0.62119 (14)0.0813 (11)
H17A0.45920.10570.61510.098*
H17B0.41600.17540.65590.098*
C180.40137 (13)0.0553 (5)0.63385 (15)0.0973 (12)
H18A0.40800.12260.60000.117*
H18B0.36280.05250.63800.117*
C190.42889 (14)0.1251 (4)0.69043 (15)0.1351 (16)
H19A0.46710.12750.68670.203*
H19B0.41590.23020.69600.203*
H19C0.42110.06170.72440.203*
C200.28068 (13)0.0593 (4)0.48471 (15)0.1021 (13)
H20A0.31330.02710.46750.153*
H20B0.28800.14730.51100.153*
H20C0.26680.02640.50710.153*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.066 (2)0.108 (3)0.0679 (19)0.0014 (18)0.0122 (16)0.0043 (18)
N20.075 (2)0.072 (2)0.0670 (19)0.0053 (18)0.0096 (17)0.0091 (18)
N30.098 (2)0.070 (2)0.081 (2)0.014 (2)0.0259 (18)0.0077 (18)
N40.098 (2)0.073 (3)0.070 (2)0.022 (2)0.0145 (18)0.0087 (18)
N50.120 (2)0.080 (2)0.078 (2)0.024 (2)0.0150 (18)0.0037 (18)
O10.1099 (19)0.096 (2)0.0706 (15)0.0253 (16)0.0285 (14)0.0151 (14)
O20.113 (2)0.095 (2)0.0846 (17)0.0356 (16)0.0278 (15)0.0050 (16)
O30.0922 (18)0.098 (2)0.0719 (16)0.0168 (16)0.0102 (14)0.0025 (15)
O40.122 (2)0.087 (2)0.116 (2)0.0410 (18)0.0185 (17)0.0034 (18)
O50.115 (2)0.092 (2)0.114 (2)0.0311 (18)0.0276 (18)0.0317 (19)
C10.073 (3)0.090 (4)0.064 (3)0.015 (3)0.005 (2)0.003 (3)
C20.086 (3)0.087 (3)0.059 (2)0.009 (3)0.017 (2)0.008 (2)
C30.090 (3)0.085 (3)0.078 (3)0.007 (3)0.018 (2)0.009 (2)
C40.082 (3)0.088 (4)0.072 (3)0.009 (3)0.000 (3)0.009 (3)
C50.074 (3)0.098 (3)0.067 (2)0.000 (2)0.0006 (17)0.012 (2)
C60.061 (2)0.081 (3)0.055 (2)0.011 (2)0.0014 (16)0.008 (2)
C70.049 (2)0.074 (3)0.064 (2)0.001 (2)0.005 (2)0.003 (2)
C80.054 (2)0.090 (3)0.061 (2)0.001 (2)0.000 (2)0.005 (2)
C90.071 (3)0.103 (4)0.084 (3)0.016 (3)0.011 (2)0.010 (3)
C100.078 (3)0.088 (3)0.109 (3)0.026 (3)0.005 (3)0.008 (3)
C110.074 (3)0.081 (4)0.084 (3)0.021 (3)0.004 (2)0.007 (3)
C120.057 (2)0.082 (3)0.061 (2)0.007 (2)0.0043 (19)0.002 (2)
C130.076 (3)0.079 (3)0.074 (2)0.009 (2)0.0054 (19)0.018 (2)
C140.077 (3)0.077 (3)0.065 (3)0.016 (3)0.008 (2)0.010 (3)
C150.090 (3)0.087 (3)0.056 (2)0.001 (2)0.013 (2)0.004 (2)
C160.077 (2)0.085 (3)0.066 (2)0.005 (2)0.008 (2)0.003 (2)
C170.087 (3)0.094 (3)0.062 (2)0.016 (2)0.003 (2)0.007 (2)
C180.096 (3)0.107 (4)0.090 (3)0.011 (3)0.017 (2)0.024 (3)
C190.144 (4)0.158 (4)0.104 (3)0.032 (3)0.010 (3)0.043 (3)
C200.106 (3)0.105 (3)0.094 (3)0.012 (3)0.004 (3)0.037 (3)
Geometric parameters (Å, º) top
N1—C51.355 (4)C7—C81.388 (4)
N1—C81.402 (4)C7—C121.407 (4)
N1—H10.8600C8—C91.374 (4)
N2—C131.280 (3)C9—C101.365 (4)
N2—N31.391 (3)C9—H90.9300
N3—C141.329 (4)C10—C111.386 (4)
N3—H30.8600C10—H100.9300
N4—C141.325 (4)C11—C121.356 (4)
N4—C151.450 (3)C12—H120.9300
N4—H40.8600C13—H130.9300
N5—C141.322 (4)C15—C161.504 (4)
N5—H5A0.8600C15—H15A0.9700
N5—H5B0.8600C15—H15B0.9700
O1—C11.272 (3)C16—C171.518 (3)
O2—C11.262 (4)C16—H16A0.9700
O3—C41.316 (4)C16—H16B0.9700
O3—H3A0.8200C17—C181.513 (4)
O4—C41.198 (4)C17—H17A0.9700
O5—C111.376 (4)C17—H17B0.9700
O5—C201.412 (3)C18—C191.516 (4)
C1—C21.477 (4)C18—H18A0.9700
C2—C31.309 (4)C18—H18B0.9700
C2—H20.9300C19—H19A0.9600
C3—C41.475 (4)C19—H19B0.9600
C3—H3B0.9300C19—H19C0.9600
C5—C61.385 (4)C20—H20A0.9600
C5—H50.9300C20—H20B0.9600
C6—C131.421 (4)C20—H20C0.9600
C6—C71.426 (4)
C5—N1—C8108.8 (3)O5—C11—C10114.6 (4)
C5—N1—H1125.6C11—C12—C7118.8 (3)
C8—N1—H1125.6C11—C12—H12120.6
C13—N2—N3115.8 (3)C7—C12—H12120.6
C14—N3—N2116.7 (3)N2—C13—C6121.7 (3)
C14—N3—H3121.6N2—C13—H13119.2
N2—N3—H3121.6C6—C13—H13119.2
C14—N4—C15126.4 (3)N5—C14—N4121.1 (4)
C14—N4—H4116.8N5—C14—N3118.5 (4)
C15—N4—H4116.8N4—C14—N3120.4 (4)
C14—N5—H5A120.0N4—C15—C16109.0 (3)
C14—N5—H5B120.0N4—C15—H15A109.9
H5A—N5—H5B120.0C16—C15—H15A109.9
C4—O3—H3A109.5N4—C15—H15B109.9
C11—O5—C20117.4 (3)C16—C15—H15B109.9
O2—C1—O1123.2 (4)H15A—C15—H15B108.3
O2—C1—C2117.0 (4)C15—C16—C17113.1 (3)
O1—C1—C2119.7 (4)C15—C16—H16A109.0
C3—C2—C1130.4 (4)C17—C16—H16A109.0
C3—C2—H2114.8C15—C16—H16B109.0
C1—C2—H2114.8C17—C16—H16B109.0
C2—C3—C4133.2 (4)H16A—C16—H16B107.8
C2—C3—H3B113.4C18—C17—C16112.4 (3)
C4—C3—H3B113.4C18—C17—H17A109.1
O4—C4—O3120.4 (4)C16—C17—H17A109.1
O4—C4—C3121.6 (4)C18—C17—H17B109.1
O3—C4—C3118.0 (4)C16—C17—H17B109.1
N1—C5—C6110.1 (3)H17A—C17—H17B107.9
N1—C5—H5125.0C17—C18—C19112.5 (3)
C6—C5—H5125.0C17—C18—H18A109.1
C5—C6—C13124.0 (4)C19—C18—H18A109.1
C5—C6—C7105.9 (3)C17—C18—H18B109.1
C13—C6—C7130.2 (3)C19—C18—H18B109.1
C8—C7—C12118.2 (4)H18A—C18—H18B107.8
C8—C7—C6108.3 (4)C18—C19—H19A109.5
C12—C7—C6133.5 (4)C18—C19—H19B109.5
C9—C8—C7123.2 (4)H19A—C19—H19B109.5
C9—C8—N1129.9 (4)C18—C19—H19C109.5
C7—C8—N1106.9 (4)H19A—C19—H19C109.5
C10—C9—C8117.0 (4)H19B—C19—H19C109.5
C10—C9—H9121.5O5—C20—H20A109.5
C8—C9—H9121.5O5—C20—H20B109.5
C9—C10—C11121.6 (4)H20A—C20—H20B109.5
C9—C10—H10119.2O5—C20—H20C109.5
C11—C10—H10119.2H20A—C20—H20C109.5
C12—C11—O5124.1 (4)H20B—C20—H20C109.5
C12—C11—C10121.3 (4)
C13—N2—N3—C14178.5 (3)C8—C9—C10—C111.1 (5)
O2—C1—C2—C3171.5 (4)C20—O5—C11—C123.3 (5)
O1—C1—C2—C39.2 (6)C20—O5—C11—C10178.5 (3)
C1—C2—C3—C40.3 (7)C9—C10—C11—C121.2 (6)
C2—C3—C4—O4174.7 (4)C9—C10—C11—O5179.5 (3)
C2—C3—C4—O34.7 (6)O5—C11—C12—C7179.1 (3)
C8—N1—C5—C60.3 (4)C10—C11—C12—C71.0 (5)
N1—C5—C6—C13179.7 (3)C8—C7—C12—C110.7 (5)
N1—C5—C6—C70.1 (4)C6—C7—C12—C11180.0 (3)
C5—C6—C7—C80.5 (3)N3—N2—C13—C6178.5 (3)
C13—C6—C7—C8179.3 (3)C5—C6—C13—N2177.9 (3)
C5—C6—C7—C12179.8 (3)C7—C6—C13—N21.9 (5)
C13—C6—C7—C120.0 (6)C15—N4—C14—N51.0 (5)
C12—C7—C8—C90.7 (5)C15—N4—C14—N3179.4 (3)
C6—C7—C8—C9179.9 (3)N2—N3—C14—N5176.8 (3)
C12—C7—C8—N1179.9 (3)N2—N3—C14—N42.8 (5)
C6—C7—C8—N10.7 (4)C14—N4—C15—C16178.8 (3)
C5—N1—C8—C9179.7 (3)N4—C15—C16—C17179.1 (2)
C5—N1—C8—C70.6 (4)C15—C16—C17—C18180.0 (3)
C7—C8—C9—C100.9 (5)C16—C17—C18—C19177.2 (3)
N1—C8—C9—C10179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.012.829 (3)159
N3—H3···O2ii0.861.972.809 (3)164
N5—H5B···O1ii0.862.032.885 (3)171
N5—H5A···O40.862.082.915 (4)165
O3—H3A···O10.821.612.432 (3)175
Symmetry codes: (i) x1/2, y+3/2, z1/2; (ii) x+1, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC16H24N5O+·C4H3O4
Mr417.47
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)24.873 (3), 8.4962 (16), 22.294 (2)
β (°) 93.732 (2)
V3)4701.3 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.55 × 0.42 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.954, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
9394, 4110, 1423
Rint0.058
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.084, 1.00
No. of reflections4110
No. of parameters273
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.12

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.012.829 (3)159.1
N3—H3···O2ii0.861.972.809 (3)163.7
N5—H5B···O1ii0.862.032.885 (3)171.3
N5—H5A···O40.862.082.915 (4)165.1
O3—H3A···O10.821.612.432 (3)174.9
Symmetry codes: (i) x1/2, y+3/2, z1/2; (ii) x+1, y+2, z+1.
 

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