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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): m1288–m1289.
Published online 2008 September 20. doi:  10.1107/S1600536808029590
PMCID: PMC2959439

Bis{2-eth­oxy-6-[2-(ethyl­ammonio)ethyl­imino­meth­yl]phenolato}thio­cyanato­zinc(II) nitrate

Abstract

The title complex, [Zn(NCS)(C13H20N2O2)2]NO3, consists of a complex mononuclear ZnII cation and a nitrate counter-anion. The ZnII ion is five-coordinate in a trigonal-bipyramidal geometry. The thio­cyanate N atom and two O atoms from two Schiff bases define the equatorial plane, and the two imine N atoms from the same two Schiff bases occupy the axial positions, with an N—Zn—N angle of 175.98 (7)°. The amine N atoms of the Schiff base ligands are protonated and are not involved in the coordination to the metal. The dihedral angle between the two substituted benzene rings is 87.7 (2)°. The nitrate counter-ions are linked to the cations through N—H(...)O hydrogen bonds.

Related literature

For background on Schiff base complexes, see: Samanta et al. (2007 [triangle]); Ghosh et al. (2006 [triangle]); Correia et al. (2006 [triangle]); Cai et al. (2006 [triangle]); Zhang et al. (2007 [triangle]). For ZnII complexes with biological properties, see: Berg & Shi (1996 [triangle]); Tarafder et al. (2002 [triangle]); Osowole et al. (2008 [triangle]); Chohan & Kausar (1993 [triangle]). For related structures, see: Eltayeb et al. (2008 [triangle]); Odoko et al. (2006 [triangle]); Tatar et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1288-scheme1.jpg

Experimental

Crystal data

  • [Zn(NCS)(C13H20N2O2)2]NO3
  • M r = 658.08
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1288-efi1.jpg
  • a = 12.619 (3) Å
  • b = 15.596 (3) Å
  • c = 16.373 (4) Å
  • β = 105.942 (3)°
  • V = 3098.5 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.91 mm−1
  • T = 298 (2) K
  • 0.32 × 0.30 × 0.28 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.759, T max = 0.784
  • 25309 measured reflections
  • 6704 independent reflections
  • 4943 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.102
  • S = 1.03
  • 6704 reflections
  • 383 parameters
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029590/bh2194sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029590/bh2194Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We acknowledge Yichun University for support of this research.

supplementary crystallographic information

Comment

The synthesis and structural investigation of Schiff base complexes have attracted much attention due to their interesting structures and wide potential applications (Samanta et al., 2007; Ghosh et al., 2006; Correia et al., 2006; Cai et al., 2006; Zhang et al., 2007). ZnII complexes play an important role in biological systems (Berg & Shi, 1996; Tarafder et al., 2002; Osowole et al., 2008; Chohan & Kausar, 1993). In this paper, the crystal structure of a new ZnII complex, (I), with the Schiff base 2-ethoxy-6-[(2-ethylammonioethylimino)methyl]phenol and thiocyanate as ligands is reported.

The asymmetric unit of (I) (Fig. 1) consists of a mononuclear ZnII complex cation and a nitrate counteranion. The ZnII ion is five-coordinate in a trigonal-bipyramidal geometry, with one thiocyanate N atom and two O atoms from two Schiff bases defining the base-plane, and with two imine N atoms from two Schiff bases occupying the axial positions. The coordination bond lengths and angles (Table 1) are comparable with those found in related structures (Eltayeb et al., 2008; Odoko et al., 2006; Tatar et al., 2002). The dihedral angle between the two substituted benzene rings is 87.7 (2)°. The nitrate counterions are linked to the complex cations through intermolecular N—H···O hydrogen bonds (Table 2, Fig. 2).

Experimental

The Schiff base was synthesized by condensing N-ethylethane-1,2-diamine with 3-ethoxysalicylaldehyde. The compound (0.236 g, 1.0 mmol), ammonium thiocyanate (0.076 g, 1.0 mmol), and Zn(NO3)2.6H2O (0.297 g, 1.0 mmol) were heated in ethanol (30 ml) for two hours. The resulting yellow precipitate was washed with cold ethanol and dried in air. Yellow single crystals of the complex suitable for X-ray diffraction were obtained by recrystallization in methanol at room temperature over a week.

Refinement

All H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å, N—H 0.90 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Ueq(C) and 1.2Ueq(N). A rotating group model was used for the methyl groups.

Figures

Fig. 1.
The structure of the title complex, showing 30% probability displacement ellipsoids and the atomic numbering scheme. H atoms have been omitted for clarity.
Fig. 2.
A part of the packing structure of the title complex.

Crystal data

[Zn(NCS)(C13H20N2O2)2]NO3F(000) = 1384
Mr = 658.08Dx = 1.411 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5860 reflections
a = 12.619 (3) Åθ = 2.4–25.0°
b = 15.596 (3) ŵ = 0.91 mm1
c = 16.373 (4) ÅT = 298 K
β = 105.942 (3)°Block, yellow
V = 3098.5 (12) Å30.32 × 0.30 × 0.28 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer6704 independent reflections
Radiation source: fine-focus sealed tube4943 reflections with I > 2σ(I)
graphiteRint = 0.039
ω scansθmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.759, Tmax = 0.784k = −19→19
25309 measured reflectionsl = −20→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0499P)2 + 0.4058P] where P = (Fo2 + 2Fc2)/3
6704 reflections(Δ/σ)max < 0.001
383 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = −0.24 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Zn10.16270 (2)0.137705 (16)0.239060 (17)0.03736 (10)
S10.23354 (8)0.13520 (6)0.53956 (5)0.0790 (3)
O10.06063 (12)0.04409 (9)0.19068 (10)0.0431 (4)
O2−0.10767 (13)−0.02591 (11)0.08270 (10)0.0489 (4)
O30.24094 (12)0.19615 (10)0.16454 (10)0.0422 (4)
O40.36595 (13)0.23273 (11)0.06500 (10)0.0512 (4)
O50.63860 (17)0.06593 (14)0.23141 (16)0.0828 (7)
O60.5331 (2)−0.04262 (17)0.2091 (2)0.1186 (10)
O70.70321 (18)−0.05719 (14)0.21816 (15)0.0844 (7)
N10.29156 (15)0.04450 (12)0.26479 (12)0.0397 (4)
N20.46270 (15)0.17344 (12)0.24593 (12)0.0427 (5)
H2A0.40090.17120.20250.051*
H2B0.50960.13360.23650.051*
N30.03405 (15)0.23032 (12)0.20425 (13)0.0434 (5)
N4−0.11498 (16)0.07668 (13)0.23973 (13)0.0502 (5)
H4A−0.17210.04230.21520.060*
H4B−0.05790.06080.22020.060*
N50.18116 (19)0.15588 (14)0.36497 (15)0.0561 (6)
N60.62424 (19)−0.01249 (16)0.22004 (15)0.0592 (6)
C10.18606 (19)−0.06203 (13)0.16659 (14)0.0382 (5)
C20.08048 (18)−0.02498 (13)0.15115 (14)0.0357 (5)
C3−0.00785 (19)−0.06361 (14)0.09016 (14)0.0401 (5)
C40.0100 (2)−0.13289 (15)0.04369 (16)0.0507 (6)
H4−0.0482−0.15580.00150.061*
C50.1139 (2)−0.16862 (16)0.05934 (18)0.0561 (7)
H50.1252−0.21580.02800.067*
C60.2000 (2)−0.13502 (15)0.12040 (17)0.0501 (6)
H60.2689−0.16080.13160.060*
C70.28236 (19)−0.02800 (14)0.22705 (15)0.0411 (5)
H70.3447−0.06260.24010.049*
C80.3959 (2)0.06192 (16)0.32864 (16)0.0492 (6)
H8A0.45170.02300.31980.059*
H8B0.38690.05070.38460.059*
C90.4351 (2)0.15274 (16)0.32568 (15)0.0470 (6)
H9A0.37800.19160.33230.056*
H9B0.49970.16190.37310.056*
C100.5139 (2)0.26019 (17)0.24785 (18)0.0597 (7)
H10A0.46570.30260.26220.072*
H10B0.52050.27370.19160.072*
C110.6256 (2)0.26614 (19)0.31053 (19)0.0639 (8)
H11A0.61780.26630.36720.096*
H11B0.66120.31810.30090.096*
H11C0.66940.21780.30350.096*
C12−0.2001 (2)−0.05535 (18)0.01591 (16)0.0537 (7)
H12A−0.2182−0.11400.02660.064*
H12B−0.1828−0.0535−0.03820.064*
C13−0.2952 (2)0.0027 (2)0.01422 (19)0.0710 (8)
H13A−0.3164−0.00410.06580.107*
H13B−0.3562−0.0117−0.03340.107*
H13C−0.27390.06110.00910.107*
C140.11326 (18)0.30877 (14)0.10555 (14)0.0389 (5)
C150.20996 (17)0.26120 (13)0.11291 (13)0.0355 (5)
C160.27758 (19)0.28547 (15)0.06010 (14)0.0410 (5)
C170.2535 (2)0.35687 (16)0.00929 (16)0.0551 (7)
H170.30050.3732−0.02280.066*
C180.1593 (2)0.40514 (18)0.00539 (17)0.0599 (7)
H180.14420.4542−0.02820.072*
C190.0899 (2)0.38012 (16)0.05081 (16)0.0514 (6)
H190.02520.41080.04580.062*
C200.03422 (19)0.29130 (15)0.15277 (15)0.0433 (6)
H20−0.02420.32970.14440.052*
C21−0.0571 (2)0.23231 (17)0.2451 (2)0.0602 (7)
H21A−0.09050.28880.23720.072*
H21B−0.02670.22340.30570.072*
C22−0.1456 (2)0.16612 (18)0.2113 (2)0.0644 (8)
H22A−0.21060.18210.22860.077*
H22B−0.16540.16760.14980.077*
C23−0.0843 (3)0.06135 (19)0.33260 (18)0.0655 (8)
H23A−0.14910.06760.35310.079*
H23B−0.03070.10390.36100.079*
C24−0.0368 (3)−0.0266 (2)0.3540 (2)0.0901 (11)
H24A−0.0897−0.06880.32590.135*
H24B−0.0190−0.03520.41430.135*
H24C0.0288−0.03220.33550.135*
C250.4284 (2)0.2466 (2)0.00521 (18)0.0654 (8)
H25A0.46440.30210.01510.078*
H25B0.38000.2458−0.05220.078*
C260.5126 (3)0.1772 (2)0.0158 (2)0.0878 (11)
H26A0.55750.17630.07350.132*
H26B0.55820.1878−0.02140.132*
H26C0.47620.12290.00200.132*
C270.2027 (2)0.14706 (16)0.43733 (18)0.0491 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.03578 (15)0.03238 (15)0.04647 (17)−0.00390 (11)0.01557 (12)−0.00297 (11)
S10.0852 (6)0.1015 (7)0.0522 (4)−0.0016 (5)0.0221 (4)0.0014 (4)
O10.0345 (8)0.0380 (9)0.0611 (10)−0.0048 (7)0.0202 (8)−0.0166 (7)
O20.0383 (9)0.0521 (10)0.0565 (10)−0.0086 (8)0.0135 (8)−0.0118 (8)
O30.0348 (8)0.0423 (9)0.0514 (9)0.0036 (7)0.0148 (7)0.0109 (7)
O40.0447 (10)0.0605 (11)0.0526 (10)0.0014 (8)0.0205 (8)0.0112 (8)
O50.0583 (12)0.0506 (13)0.144 (2)−0.0014 (10)0.0361 (13)−0.0036 (12)
O60.0652 (15)0.1000 (19)0.208 (3)−0.0290 (14)0.0664 (18)−0.0322 (19)
O70.0703 (14)0.0690 (14)0.125 (2)0.0200 (12)0.0454 (14)0.0028 (13)
N10.0351 (10)0.0365 (11)0.0471 (11)−0.0016 (8)0.0110 (9)0.0076 (9)
N20.0353 (10)0.0424 (11)0.0471 (11)−0.0054 (9)0.0057 (9)0.0008 (9)
N30.0396 (11)0.0345 (11)0.0600 (13)−0.0019 (8)0.0206 (9)−0.0086 (9)
N40.0392 (11)0.0513 (13)0.0690 (14)−0.0087 (9)0.0301 (10)−0.0145 (11)
N50.0614 (15)0.0613 (15)0.0481 (13)−0.0093 (11)0.0195 (11)−0.0086 (11)
N60.0469 (13)0.0566 (15)0.0828 (17)−0.0006 (11)0.0327 (12)0.0022 (12)
C10.0440 (13)0.0289 (11)0.0467 (13)−0.0014 (10)0.0209 (11)0.0035 (10)
C20.0427 (12)0.0284 (11)0.0430 (12)−0.0046 (9)0.0237 (10)−0.0008 (9)
C30.0451 (13)0.0361 (12)0.0439 (13)−0.0058 (10)0.0202 (11)−0.0015 (10)
C40.0641 (17)0.0418 (14)0.0480 (14)−0.0111 (12)0.0183 (13)−0.0100 (11)
C50.076 (2)0.0350 (13)0.0653 (17)0.0021 (13)0.0325 (15)−0.0103 (12)
C60.0604 (16)0.0337 (13)0.0645 (17)0.0086 (12)0.0312 (14)0.0036 (12)
C70.0399 (13)0.0341 (13)0.0534 (14)0.0058 (10)0.0199 (11)0.0139 (11)
C80.0429 (14)0.0505 (15)0.0510 (15)−0.0021 (11)0.0072 (12)0.0097 (12)
C90.0403 (13)0.0503 (15)0.0463 (14)−0.0073 (11)0.0050 (11)0.0006 (11)
C100.0610 (17)0.0486 (16)0.0663 (18)−0.0148 (13)0.0121 (14)0.0054 (13)
C110.0486 (16)0.0622 (18)0.081 (2)−0.0182 (13)0.0183 (15)−0.0178 (15)
C120.0517 (15)0.0602 (17)0.0445 (14)−0.0156 (13)0.0056 (12)0.0024 (12)
C130.0466 (16)0.096 (2)0.069 (2)−0.0077 (16)0.0136 (14)0.0072 (17)
C140.0402 (13)0.0331 (12)0.0389 (12)−0.0022 (10)0.0033 (10)−0.0076 (9)
C150.0357 (12)0.0312 (12)0.0353 (12)−0.0056 (9)0.0026 (9)−0.0024 (9)
C160.0407 (13)0.0423 (13)0.0369 (12)−0.0063 (10)0.0053 (10)−0.0010 (10)
C170.0661 (18)0.0554 (16)0.0433 (14)−0.0082 (14)0.0139 (13)0.0093 (12)
C180.0716 (19)0.0499 (16)0.0526 (16)0.0057 (14)0.0074 (14)0.0137 (13)
C190.0548 (16)0.0429 (14)0.0494 (15)0.0095 (12)0.0021 (13)−0.0005 (11)
C200.0362 (12)0.0352 (13)0.0550 (14)0.0027 (10)0.0066 (11)−0.0122 (11)
C210.0563 (16)0.0442 (15)0.093 (2)0.0027 (12)0.0424 (16)−0.0065 (14)
C220.0434 (15)0.0602 (18)0.100 (2)0.0053 (13)0.0371 (16)0.0020 (16)
C230.0709 (19)0.0653 (19)0.071 (2)−0.0144 (15)0.0375 (16)−0.0140 (15)
C240.099 (3)0.082 (2)0.097 (3)−0.001 (2)0.041 (2)0.019 (2)
C250.0595 (18)0.083 (2)0.0630 (18)−0.0080 (16)0.0326 (15)0.0040 (15)
C260.080 (2)0.084 (2)0.121 (3)0.002 (2)0.064 (2)0.004 (2)
C270.0440 (14)0.0466 (15)0.0622 (17)−0.0063 (11)0.0240 (13)−0.0089 (12)

Geometric parameters (Å, °)

Zn1—O11.9641 (15)C9—H9A0.9700
Zn1—O31.9890 (15)C9—H9B0.9700
Zn1—N52.030 (2)C10—C111.502 (4)
Zn1—N32.1305 (19)C10—H10A0.9700
Zn1—N12.1351 (19)C10—H10B0.9700
S1—C271.622 (3)C11—H11A0.9600
O1—C21.316 (2)C11—H11B0.9600
O2—C31.365 (3)C11—H11C0.9600
O2—C121.438 (3)C12—C131.497 (4)
O3—C151.310 (2)C12—H12A0.9700
O4—C161.370 (3)C12—H12B0.9700
O4—C251.432 (3)C13—H13A0.9600
O5—N61.243 (3)C13—H13B0.9600
O6—N61.209 (3)C13—H13C0.9600
O7—N61.223 (3)C14—C151.405 (3)
N1—C71.278 (3)C14—C191.408 (3)
N1—C81.464 (3)C14—C201.446 (3)
N2—C91.477 (3)C15—C161.423 (3)
N2—C101.496 (3)C16—C171.373 (3)
N2—H2A0.9000C17—C181.393 (4)
N2—H2B0.9000C17—H170.9300
N3—C201.271 (3)C18—C191.353 (4)
N3—C211.481 (3)C18—H180.9300
N4—C231.482 (3)C19—H190.9300
N4—C221.488 (3)C20—H200.9300
N4—H4A0.9000C21—C221.510 (4)
N4—H4B0.9000C21—H21A0.9700
N5—C271.149 (3)C21—H21B0.9700
C1—C61.404 (3)C22—H22A0.9700
C1—C21.410 (3)C22—H22B0.9700
C1—C71.441 (3)C23—C241.500 (4)
C2—C31.411 (3)C23—H23A0.9700
C3—C41.375 (3)C23—H23B0.9700
C4—C51.383 (4)C24—H24A0.9600
C4—H40.9300C24—H24B0.9600
C5—C61.363 (4)C24—H24C0.9600
C5—H50.9300C25—C261.493 (4)
C6—H60.9300C25—H25A0.9700
C7—H70.9300C25—H25B0.9700
C8—C91.505 (3)C26—H26A0.9600
C8—H8A0.9700C26—H26B0.9600
C8—H8B0.9700C26—H26C0.9600
O1—Zn1—O3118.31 (7)C10—C11—H11B109.5
O1—Zn1—N5113.14 (8)H11A—C11—H11B109.5
O3—Zn1—N5128.40 (8)C10—C11—H11C109.5
O1—Zn1—N391.66 (7)H11A—C11—H11C109.5
O3—Zn1—N389.74 (7)H11B—C11—H11C109.5
N5—Zn1—N392.49 (9)O2—C12—C13107.4 (2)
O1—Zn1—N187.31 (7)O2—C12—H12A110.2
O3—Zn1—N187.34 (7)C13—C12—H12A110.2
N5—Zn1—N191.49 (8)O2—C12—H12B110.2
N3—Zn1—N1175.98 (7)C13—C12—H12B110.2
C2—O1—Zn1127.92 (13)H12A—C12—H12B108.5
C3—O2—C12117.82 (19)C12—C13—H13A109.5
C15—O3—Zn1129.83 (14)C12—C13—H13B109.5
C16—O4—C25117.45 (19)H13A—C13—H13B109.5
C7—N1—C8117.0 (2)C12—C13—H13C109.5
C7—N1—Zn1122.93 (16)H13A—C13—H13C109.5
C8—N1—Zn1120.08 (15)H13B—C13—H13C109.5
C9—N2—C10112.61 (19)C15—C14—C19119.8 (2)
C9—N2—H2A109.1C15—C14—C20124.4 (2)
C10—N2—H2A109.1C19—C14—C20115.7 (2)
C9—N2—H2B109.1O3—C15—C14124.2 (2)
C10—N2—H2B109.1O3—C15—C16118.4 (2)
H2A—N2—H2B107.8C14—C15—C16117.3 (2)
C20—N3—C21115.3 (2)O4—C16—C17124.3 (2)
C20—N3—Zn1123.00 (16)O4—C16—C15114.78 (19)
C21—N3—Zn1121.50 (17)C17—C16—C15120.9 (2)
C23—N4—C22116.4 (2)C16—C17—C18120.7 (3)
C23—N4—H4A108.2C16—C17—H17119.7
C22—N4—H4A108.2C18—C17—H17119.7
C23—N4—H4B108.2C19—C18—C17119.5 (2)
C22—N4—H4B108.2C19—C18—H18120.3
H4A—N4—H4B107.4C17—C18—H18120.3
C27—N5—Zn1163.6 (2)C18—C19—C14121.6 (2)
O6—N6—O7121.5 (3)C18—C19—H19119.2
O6—N6—O5119.9 (2)C14—C19—H19119.2
O7—N6—O5118.6 (2)N3—C20—C14128.5 (2)
C6—C1—C2119.2 (2)N3—C20—H20115.7
C6—C1—C7117.5 (2)C14—C20—H20115.7
C2—C1—C7123.3 (2)N3—C21—C22114.1 (2)
O1—C2—C1123.1 (2)N3—C21—H21A108.7
O1—C2—C3118.5 (2)C22—C21—H21A108.7
C1—C2—C3118.4 (2)N3—C21—H21B108.7
O2—C3—C4125.2 (2)C22—C21—H21B108.7
O2—C3—C2114.18 (19)H21A—C21—H21B107.6
C4—C3—C2120.6 (2)N4—C22—C21115.1 (2)
C3—C4—C5120.3 (2)N4—C22—H22A108.5
C3—C4—H4119.8C21—C22—H22A108.5
C5—C4—H4119.8N4—C22—H22B108.5
C6—C5—C4120.3 (2)C21—C22—H22B108.5
C6—C5—H5119.8H22A—C22—H22B107.5
C4—C5—H5119.8N4—C23—C24111.2 (2)
C5—C6—C1121.0 (2)N4—C23—H23A109.4
C5—C6—H6119.5C24—C23—H23A109.4
C1—C6—H6119.5N4—C23—H23B109.4
N1—C7—C1127.2 (2)C24—C23—H23B109.4
N1—C7—H7116.4H23A—C23—H23B108.0
C1—C7—H7116.4C23—C24—H24A109.5
N1—C8—C9112.99 (19)C23—C24—H24B109.5
N1—C8—H8A109.0H24A—C24—H24B109.5
C9—C8—H8A109.0C23—C24—H24C109.5
N1—C8—H8B109.0H24A—C24—H24C109.5
C9—C8—H8B109.0H24B—C24—H24C109.5
H8A—C8—H8B107.8O4—C25—C26108.6 (2)
N2—C9—C8113.2 (2)O4—C25—H25A110.0
N2—C9—H9A108.9C26—C25—H25A110.0
C8—C9—H9A108.9O4—C25—H25B110.0
N2—C9—H9B108.9C26—C25—H25B110.0
C8—C9—H9B108.9H25A—C25—H25B108.4
H9A—C9—H9B107.8C25—C26—H26A109.5
N2—C10—C11112.9 (2)C25—C26—H26B109.5
N2—C10—H10A109.0H26A—C26—H26B109.5
C11—C10—H10A109.0C25—C26—H26C109.5
N2—C10—H10B109.0H26A—C26—H26C109.5
C11—C10—H10B109.0H26B—C26—H26C109.5
H10A—C10—H10B107.8N5—C27—S1179.6 (3)
C10—C11—H11A109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2B···O50.901.962.843 (3)166
N2—H2A···O30.901.982.772 (2)146
N2—H2A···O40.902.373.022 (3)129
N4—H4A···O7i0.902.223.050 (3)153
N4—H4A···O5i0.902.503.080 (3)122
N4—H4B···O10.901.712.606 (2)171
N4—H4B···O20.902.553.051 (3)116

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2194).

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