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In the title compound, [ZnCl2(C14H23N5)]·CH3OH, the Zn atom is coordinated by two N atoms and two Cl atoms in an approximately tetra­hedral arrangement. The dihedral angle between the N—Zn—N and Cl—Zn—Cl planes is 89.69 (5)°. The methanol solvent mol­ecule takes part in the formation of the hydrogen-bond system.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048179/rk2043sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048179/rk2043Isup2.hkl
Contains datablock I

CCDC reference: 667128

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.028
  • wR factor = 0.082
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of N3 = ... R PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn (2) 1.93
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

The ligand, bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine, synthesized (Sorrell & Malachowski, 1983) and its complex of cobalt, copper or zinc was reported (van Berkel et al., 1994). Nickel complex of the ligand was reported as an efficient catalyst for dimerization of enthylene to 1–butene (Ajellal et al., 2006). Aluminium and zinc alkyl complexes bearing the ligand were synthesized and show the activities on polymerization of methyl methacrylate and lactide (Lian et al., 2007). Also palladium complexes containing the ligand were reported (Pañella et al., 2006; Mendoza et al., 2006). In the title complex, the ligand acts as bidentate though it is a potential tridentate. However, the ligand was κ3 bonding mode at zinc from reaction ZnCl2–to–ligand ratio of 2:1 (van Berkel et al., 1994). Herein, we report the crystal structure of Zn(II) complex containing bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine as bidentate. The geometry around Zn(II) is an approximately tetrahedron. The dihedral angle between N—Zn—N and Cl—Zn—Cl planes is 89.69 (5)°.

The methanol solvate molecule takes part in the formation of H–bonds system: the hydroxo–group of one is a donor and acceptor in this system - see table of hydrogen–bond geometry.

Related literature top

For the synthesis of bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine see: Sorrell & Malachowski, (1983). For related structures see: van Berkel et al. (1994); Ajellal et al. (2006); Pañella et al. (2006); Mendoza et al. (2006); Lian et al. (2007).

Experimental top

To bis{2–(3,5–dimethyl–1–pyrazolyl)ethyl}amine (1.67 g, 6.4 mmol) was added dropwise a solution of ZnCl2 (0.87 g, 6.4 mmol) in methanol (20 ml). The mixture was stirred for 1 day at room temperature. The solvent was removed and the residue was washed with ether to give white solids. Colorless crystals was obtained from methanol solution. Yield; 1.63 g (64%). Anal. Calculated for C15H27Cl2N5OZn: C, 41.93; H, 6.33; N, 16.30. Found: C, 42.09; H, 6.24; N, 16.46%. 1H NMR (DMSO–d6); δ 5.97 (s, H-Pz), 4.20 (t, CH2-Pz, J=6.0, 5.7 Hz), 3.07 (t, NCH2–, J=5.7, 5.4 Hz), 2.25 (s, CH3-Pz), 2.18 (s, CH3-Pz), where Pz - pyrazolyl.

Refinement top

All H atoms, except H atoms of hydroxy and amine groups, which were refined isotropically, were positioned geometrically and refined using a riding model, with C—H = 0.97Å and Uiso(H) = 1.2Ueq(C) for CH2, and C—H = 0.96Å and Uiso(H) = 1.5Ueq(C) for CH3 H atoms.

Structure description top

The ligand, bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine, synthesized (Sorrell & Malachowski, 1983) and its complex of cobalt, copper or zinc was reported (van Berkel et al., 1994). Nickel complex of the ligand was reported as an efficient catalyst for dimerization of enthylene to 1–butene (Ajellal et al., 2006). Aluminium and zinc alkyl complexes bearing the ligand were synthesized and show the activities on polymerization of methyl methacrylate and lactide (Lian et al., 2007). Also palladium complexes containing the ligand were reported (Pañella et al., 2006; Mendoza et al., 2006). In the title complex, the ligand acts as bidentate though it is a potential tridentate. However, the ligand was κ3 bonding mode at zinc from reaction ZnCl2–to–ligand ratio of 2:1 (van Berkel et al., 1994). Herein, we report the crystal structure of Zn(II) complex containing bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine as bidentate. The geometry around Zn(II) is an approximately tetrahedron. The dihedral angle between N—Zn—N and Cl—Zn—Cl planes is 89.69 (5)°.

The methanol solvate molecule takes part in the formation of H–bonds system: the hydroxo–group of one is a donor and acceptor in this system - see table of hydrogen–bond geometry.

For the synthesis of bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine see: Sorrell & Malachowski, (1983). For related structures see: van Berkel et al. (1994); Ajellal et al. (2006); Pañella et al. (2006); Mendoza et al. (2006); Lian et al. (2007).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989; data reduction: XCAD (McArdle, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. A view of the dichlorido{bis[2–(3,5–dimethylpyrazol–1–yl)ethyl]amine–κ2N,N'}zinc with the numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms are drawn as a spheres with arbitrary radius.
{Bis[2-(3,5-dimethylpyrazol-1-yl)ethyl]amine- κ2N,N'}dichloridozinc(II) methanol solvate top
Crystal data top
[ZnCl2(C14H23N5)]·CH4OZ = 2
Mr = 429.71F(000) = 448
Triclinic, P1Dx = 1.411 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 9.3550 (6) ÅCell parameters from 25 reflections
b = 9.3562 (4) Åθ = 10.6–13.2°
c = 13.3177 (7) ŵ = 1.49 mm1
α = 83.362 (4)°T = 293 K
β = 72.448 (5)°Block, colourless
γ = 65.563 (4)°0.45 × 0.40 × 0.35 mm
V = 1011.77 (10) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
3209 reflections with I > 2σ(I)
Radiation source: Fine–focus sealed tubeRint = 0.008
Graphite monochromatorθmax = 25.5°, θmin = 1.6°
Scintillation counter scansh = 011
Absorption correction: ψ scan
(ABSCALC; McArdle & Daly, 1999)
k = 1011
Tmin = 0.517, Tmax = 0.594l = 1516
4135 measured reflections3 standard reflections every 60 min
3753 independent reflections intensity decay: 0.2%
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)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0529P)2 + 0.1929P]
where P = (Fo2 + 2Fc2)/3
3753 reflections(Δ/σ)max < 0.001
225 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
[ZnCl2(C14H23N5)]·CH4Oγ = 65.563 (4)°
Mr = 429.71V = 1011.77 (10) Å3
Triclinic, P1Z = 2
a = 9.3550 (6) ÅMo Kα radiation
b = 9.3562 (4) ŵ = 1.49 mm1
c = 13.3177 (7) ÅT = 293 K
α = 83.362 (4)°0.45 × 0.40 × 0.35 mm
β = 72.448 (5)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
3209 reflections with I > 2σ(I)
Absorption correction: ψ scan
(ABSCALC; McArdle & Daly, 1999)
Rint = 0.008
Tmin = 0.517, Tmax = 0.5943 standard reflections every 60 min
4135 measured reflections intensity decay: 0.2%
3753 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.38 e Å3
3753 reflectionsΔρmin = 0.33 e Å3
225 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn0.50037 (3)0.75209 (3)0.161235 (17)0.04246 (10)
Cl10.53380 (8)0.54111 (7)0.26152 (5)0.06128 (16)
Cl20.27310 (8)0.86417 (8)0.10889 (5)0.06388 (17)
N10.7028 (2)0.7171 (2)0.03740 (13)0.0458 (4)
C10.7535 (3)0.6476 (2)0.05640 (15)0.0455 (4)
C20.6472 (3)0.5905 (3)0.09021 (19)0.0612 (6)
H2A0.67680.48100.07450.092*
H2B0.66200.60530.16460.092*
H2C0.53480.64860.05320.092*
C30.9078 (3)0.6424 (2)0.10956 (16)0.0480 (5)
H30.97030.59940.17610.058*
C40.9508 (2)0.7128 (2)0.04526 (15)0.0426 (4)
C51.0994 (3)0.7445 (3)0.06226 (18)0.0572 (5)
H5A1.07350.85410.07600.086*
H5B1.18340.68370.12130.086*
H5C1.13720.71630.00040.086*
N20.8257 (2)0.7571 (2)0.04240 (12)0.0435 (4)
C60.8102 (3)0.8360 (3)0.13570 (17)0.0573 (6)
H6A0.89660.87390.12020.069*
H6B0.82500.76060.19210.069*
C70.6463 (3)0.9729 (3)0.17301 (18)0.0551 (5)
H7A0.65791.04600.21280.066*
H7B0.61211.02760.11240.066*
N30.5195 (2)0.9201 (2)0.23970 (13)0.0419 (4)
H3N0.549 (3)0.874 (3)0.2914 (18)0.039 (6)*
C80.3639 (3)1.0539 (2)0.28370 (16)0.0469 (4)
H8A0.31401.10540.22800.056*
H8B0.38421.12960.31510.056*
C90.2496 (3)0.9949 (3)0.36641 (17)0.0493 (5)
H9A0.21680.93190.33240.059*
H9B0.30740.92820.41510.059*
N40.1048 (2)1.1224 (2)0.42467 (13)0.0476 (4)
N50.1135 (2)1.1900 (2)0.50638 (14)0.0518 (4)
C100.0371 (3)1.2995 (3)0.54475 (18)0.0545 (5)
C110.0740 (4)1.3975 (4)0.6380 (2)0.0752 (8)
H11A0.13891.36470.69890.113*
H11B0.13321.50590.62440.113*
H11C0.02661.38480.65030.113*
C120.1397 (3)1.3013 (3)0.4873 (2)0.0573 (6)
H120.24971.36710.49840.069*
C130.0471 (3)1.1874 (3)0.41129 (17)0.0500 (5)
C140.0908 (3)1.1326 (3)0.3282 (2)0.0667 (6)
H14A0.00511.11540.26340.100*
H14B0.19111.21090.31800.100*
H14C0.10411.03630.34980.100*
C150.4334 (4)0.2736 (4)0.4990 (3)0.0890 (9)
H1510.35270.33630.46360.134*
H1520.53110.20850.44860.134*
H1530.45790.34100.53420.134*
O0.3734 (3)0.1799 (3)0.57224 (17)0.0806 (6)
H1O0.306 (4)0.161 (4)0.561 (3)0.081 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.04342 (14)0.04865 (15)0.03929 (14)0.02289 (10)0.00885 (10)0.00452 (9)
Cl10.0659 (3)0.0536 (3)0.0568 (3)0.0239 (3)0.0080 (3)0.0041 (2)
Cl20.0606 (3)0.0711 (4)0.0668 (4)0.0204 (3)0.0321 (3)0.0099 (3)
N10.0505 (9)0.0558 (10)0.0378 (8)0.0310 (8)0.0053 (7)0.0068 (7)
C10.0583 (12)0.0434 (10)0.0379 (10)0.0248 (9)0.0102 (9)0.0027 (8)
C20.0751 (16)0.0703 (15)0.0517 (13)0.0436 (13)0.0101 (11)0.0144 (11)
C30.0528 (11)0.0489 (11)0.0370 (10)0.0184 (9)0.0052 (9)0.0075 (8)
C40.0410 (10)0.0439 (10)0.0379 (9)0.0133 (8)0.0089 (8)0.0004 (8)
C50.0402 (11)0.0761 (15)0.0513 (12)0.0205 (10)0.0072 (9)0.0100 (11)
N20.0427 (9)0.0531 (9)0.0376 (8)0.0223 (7)0.0086 (7)0.0056 (7)
C60.0487 (12)0.0872 (16)0.0444 (11)0.0358 (11)0.0048 (9)0.0203 (11)
C70.0607 (13)0.0643 (13)0.0478 (11)0.0389 (11)0.0015 (10)0.0180 (10)
N30.0440 (9)0.0495 (9)0.0341 (8)0.0211 (7)0.0085 (7)0.0038 (7)
C80.0506 (11)0.0474 (11)0.0410 (10)0.0201 (9)0.0075 (9)0.0055 (8)
C90.0449 (11)0.0507 (11)0.0452 (11)0.0157 (9)0.0076 (9)0.0000 (9)
N40.0407 (9)0.0569 (10)0.0405 (9)0.0157 (8)0.0098 (7)0.0015 (7)
N50.0438 (9)0.0649 (11)0.0437 (9)0.0197 (8)0.0098 (8)0.0035 (8)
C100.0470 (11)0.0623 (13)0.0500 (12)0.0243 (10)0.0023 (9)0.0046 (10)
C110.0654 (16)0.0877 (19)0.0651 (16)0.0284 (14)0.0016 (13)0.0250 (14)
C120.0377 (10)0.0615 (13)0.0662 (14)0.0155 (10)0.0108 (10)0.0020 (11)
C130.0426 (11)0.0608 (13)0.0502 (12)0.0249 (10)0.0145 (9)0.0077 (10)
C140.0623 (15)0.0826 (17)0.0657 (15)0.0330 (13)0.0271 (12)0.0016 (13)
C150.091 (2)0.102 (2)0.098 (2)0.0493 (19)0.0520 (19)0.0208 (19)
O0.0804 (13)0.1126 (17)0.0730 (13)0.0492 (13)0.0461 (11)0.0182 (11)
Geometric parameters (Å, º) top
Zn—N12.0349 (16)N3—H3N0.83 (2)
Zn—N32.0787 (17)C8—C91.516 (3)
Zn—Cl12.2158 (6)C8—H8A0.9700
Zn—Cl22.2330 (6)C8—H8B0.9700
N1—C11.335 (2)C9—N41.450 (3)
N1—N21.369 (2)C9—H9A0.9700
C1—C31.386 (3)C9—H9B0.9700
C1—C21.497 (3)N4—C131.354 (3)
C2—H2A0.9600N4—N51.359 (3)
C2—H2B0.9600N5—C101.337 (3)
C2—H2C0.9600C10—C121.391 (3)
C3—C41.374 (3)C10—C111.498 (3)
C3—H30.9300C11—H11A0.9600
C4—N21.338 (2)C11—H11B0.9600
C4—C51.485 (3)C11—H11C0.9600
C5—H5A0.9600C12—C131.366 (3)
C5—H5B0.9600C12—H120.9300
C5—H5C0.9600C13—C141.494 (3)
N2—C61.458 (3)C14—H14A0.9600
C6—C71.517 (3)C14—H14B0.9600
C6—H6A0.9700C14—H14C0.9600
C6—H6B0.9700C15—O1.383 (4)
C7—N31.479 (3)C15—H1510.9600
C7—H7A0.9700C15—H1520.9600
C7—H7B0.9700C15—H1530.9600
N3—C81.476 (3)O—H1O0.78 (3)
N1—Zn—N397.10 (6)C8—N3—H3N105.1 (15)
N1—Zn—Cl1111.06 (5)C7—N3—H3N108.8 (15)
N3—Zn—Cl1107.94 (5)Zn—N3—H3N104.9 (15)
N1—Zn—Cl2110.94 (5)N3—C8—C9109.32 (17)
N3—Zn—Cl2108.51 (5)N3—C8—H8A109.8
Cl1—Zn—Cl2118.95 (3)C9—C8—H8A109.8
C1—N1—N2105.84 (16)N3—C8—H8B109.8
C1—N1—Zn132.04 (15)C9—C8—H8B109.8
N2—N1—Zn121.97 (12)H8A—C8—H8B108.3
N1—C1—C3109.52 (18)N4—C9—C8112.15 (18)
N1—C1—C2120.74 (19)N4—C9—H9A109.2
C3—C1—C2129.74 (19)C8—C9—H9A109.2
C1—C2—H2A109.5N4—C9—H9B109.2
C1—C2—H2B109.5C8—C9—H9B109.2
H2A—C2—H2B109.5H9A—C9—H9B107.9
C1—C2—H2C109.5C13—N4—N5111.80 (17)
H2A—C2—H2C109.5C13—N4—C9129.17 (19)
H2B—C2—H2C109.5N5—N4—C9119.02 (17)
C4—C3—C1106.98 (17)C10—N5—N4105.05 (18)
C4—C3—H3126.5N5—C10—C12110.4 (2)
C1—C3—H3126.5N5—C10—C11119.9 (2)
N2—C4—C3106.46 (18)C12—C10—C11129.6 (2)
N2—C4—C5122.74 (19)C10—C11—H11A109.5
C3—C4—C5130.78 (19)C10—C11—H11B109.5
C4—C5—H5A109.5H11A—C11—H11B109.5
C4—C5—H5B109.5C10—C11—H11C109.5
H5A—C5—H5B109.5H11A—C11—H11C109.5
C4—C5—H5C109.5H11B—C11—H11C109.5
H5A—C5—H5C109.5C13—C12—C10106.5 (2)
H5B—C5—H5C109.5C13—C12—H12126.7
C4—N2—N1111.20 (16)C10—C12—H12126.7
C4—N2—C6128.46 (17)N4—C13—C12106.2 (2)
N1—N2—C6120.34 (16)N4—C13—C14122.7 (2)
N2—C6—C7113.19 (19)C12—C13—C14131.1 (2)
N2—C6—H6A108.9C13—C14—H14A109.5
C7—C6—H6A108.9C13—C14—H14B109.5
N2—C6—H6B108.9H14A—C14—H14B109.5
C7—C6—H6B108.9C13—C14—H14C109.5
H6A—C6—H6B107.8H14A—C14—H14C109.5
N3—C7—C6111.62 (19)H14B—C14—H14C109.5
N3—C7—H7A109.3O—C15—H151109.5
C6—C7—H7A109.3O—C15—H152109.5
N3—C7—H7B109.3H151—C15—H152109.5
C6—C7—H7B109.3O—C15—H153109.5
H7A—C7—H7B108.0H151—C15—H153109.5
C8—N3—C7111.73 (17)H152—C15—H153109.5
C8—N3—Zn114.97 (13)C15—O—H1O116 (2)
C7—N3—Zn110.82 (12)
N3—Zn—N1—C1164.96 (19)C6—C7—N3—C8175.01 (17)
Cl1—Zn—N1—C182.7 (2)C6—C7—N3—Zn55.4 (2)
Cl2—Zn—N1—C152.0 (2)N1—Zn—N3—C8137.79 (14)
N3—Zn—N1—N220.20 (16)Cl1—Zn—N3—C8107.31 (13)
Cl1—Zn—N1—N292.17 (15)Cl2—Zn—N3—C822.86 (15)
Cl2—Zn—N1—N2133.17 (14)N1—Zn—N3—C79.90 (16)
N2—N1—C1—C30.6 (2)Cl1—Zn—N3—C7124.80 (15)
Zn—N1—C1—C3174.84 (15)Cl2—Zn—N3—C7105.03 (15)
N2—N1—C1—C2178.83 (19)C7—N3—C8—C9169.66 (18)
Zn—N1—C1—C25.7 (3)Zn—N3—C8—C962.9 (2)
N1—C1—C3—C40.5 (2)N3—C8—C9—N4170.79 (17)
C2—C1—C3—C4178.9 (2)C8—C9—N4—C1398.9 (3)
C1—C3—C4—N20.1 (2)C8—C9—N4—N582.3 (2)
C1—C3—C4—C5178.0 (2)C13—N4—N5—C100.1 (2)
C3—C4—N2—N10.2 (2)C9—N4—N5—C10178.89 (19)
C5—C4—N2—N1178.60 (19)N4—N5—C10—C120.3 (3)
C3—C4—N2—C6179.6 (2)N4—N5—C10—C11179.1 (2)
C5—C4—N2—C62.1 (3)N5—C10—C12—C130.3 (3)
C1—N1—N2—C40.5 (2)C11—C10—C12—C13179.0 (3)
Zn—N1—N2—C4175.48 (13)N5—N4—C13—C120.0 (2)
C1—N1—N2—C6179.9 (2)C9—N4—C13—C12178.9 (2)
Zn—N1—N2—C63.9 (3)N5—N4—C13—C14178.8 (2)
C4—N2—C6—C7133.5 (2)C9—N4—C13—C140.1 (4)
N1—N2—C6—C747.2 (3)C10—C12—C13—N40.2 (3)
N2—C6—C7—N383.4 (2)C10—C12—C13—C14178.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O—H1O···N5i0.78 (4)2.04 (4)2.787 (3)159 (3)
N3—H3N···Oii0.83 (3)2.09 (2)2.889 (3)163 (2)
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[ZnCl2(C14H23N5)]·CH4O
Mr429.71
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.3550 (6), 9.3562 (4), 13.3177 (7)
α, β, γ (°)83.362 (4), 72.448 (5), 65.563 (4)
V3)1011.77 (10)
Z2
Radiation typeMo Kα
µ (mm1)1.49
Crystal size (mm)0.45 × 0.40 × 0.35
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(ABSCALC; McArdle & Daly, 1999)
Tmin, Tmax0.517, 0.594
No. of measured, independent and
observed [I > 2σ(I)] reflections
4135, 3753, 3209
Rint0.008
(sin θ/λ)max1)0.605
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.082, 1.04
No. of reflections3753
No. of parameters225
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.38, 0.33

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software (Enraf–Nonius, 1989, XCAD (McArdle, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O—H1O···N5i0.78 (4)2.04 (4)2.787 (3)159 (3)
N3—H3N···Oii0.83 (3)2.09 (2)2.889 (3)163 (2)
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z+1.
 

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