Bis{2-eth-oxy-6-[2-(ethyl-ammonio)ethyl-imino-meth-yl]phenolato}thio-cyanato-zinc(II) nitrate.

The title complex, [Zn(NCS)(C(13)H(20)N(2)O(2))(2)]NO(3), consists of a complex mononuclear Zn(II) cation and a nitrate counter-anion. The Zn(II) ion is five-coordinate in a trigonal-bipyramidal geometry. The thio-cyanate 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 ▶); Ghosh et al. (2006 ▶); Correia et al. (2006 ▶); Cai et al. (2006 ▶); Zhang et al. (2007 ▶). For ZnII complexes with biological properties, see: Berg & Shi (1996 ▶); Tarafder et al. (2002 ▶); Osowole et al. (2008 ▶); Chohan & Kausar (1993 ▶). For related structures, see: Eltayeb et al. (2008 ▶); Odoko et al. (2006 ▶); Tatar et al. (2002 ▶).

Experimental

Crystal data

[Zn(NCS)(C13H20N2O2)2]NO3

M = 658.08

Monoclinic,

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

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

[Zn(NCS)(C13H20N2O2)2]NO3	F(000) = 1384
Mr = 658.08	Dx = 1.411 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5860 reflections
a = 12.619 (3) Å	θ = 2.4–25.0°
b = 15.596 (3) Å	µ = 0.91 mm−1
c = 16.373 (4) Å	T = 298 K
β = 105.942 (3)°	Block, yellow
V = 3098.5 (12) Å3	0.32 × 0.30 × 0.28 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	6704 independent reflections
Radiation source: fine-focus sealed tube	4943 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω scans	θmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.759, Tmax = 0.784	k = −19→19
25309 measured reflections	l = −20→20

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0499P)2 + 0.4058P] where P = (Fo2 + 2Fc2)/3
6704 reflections	(Δ/σ)max < 0.001
383 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

	x	y	z	Uiso*/Ueq
Zn1	0.16270 (2)	0.137705 (16)	0.239060 (17)	0.03736 (10)
S1	0.23354 (8)	0.13520 (6)	0.53956 (5)	0.0790 (3)
O1	0.06063 (12)	0.04409 (9)	0.19068 (10)	0.0431 (4)
O2	−0.10767 (13)	−0.02591 (11)	0.08270 (10)	0.0489 (4)
O3	0.24094 (12)	0.19615 (10)	0.16454 (10)	0.0422 (4)
O4	0.36595 (13)	0.23273 (11)	0.06500 (10)	0.0512 (4)
O5	0.63860 (17)	0.06593 (14)	0.23141 (16)	0.0828 (7)
O6	0.5331 (2)	−0.04262 (17)	0.2091 (2)	0.1186 (10)
O7	0.70321 (18)	−0.05719 (14)	0.21816 (15)	0.0844 (7)
N1	0.29156 (15)	0.04450 (12)	0.26479 (12)	0.0397 (4)
N2	0.46270 (15)	0.17344 (12)	0.24593 (12)	0.0427 (5)
H2A	0.4009	0.1712	0.2025	0.051*
H2B	0.5096	0.1336	0.2365	0.051*
N3	0.03405 (15)	0.23032 (12)	0.20425 (13)	0.0434 (5)
N4	−0.11498 (16)	0.07668 (13)	0.23973 (13)	0.0502 (5)
H4A	−0.1721	0.0423	0.2152	0.060*
H4B	−0.0579	0.0608	0.2202	0.060*
N5	0.18116 (19)	0.15588 (14)	0.36497 (15)	0.0561 (6)
N6	0.62424 (19)	−0.01249 (16)	0.22004 (15)	0.0592 (6)
C1	0.18606 (19)	−0.06203 (13)	0.16659 (14)	0.0382 (5)
C2	0.08048 (18)	−0.02498 (13)	0.15115 (14)	0.0357 (5)
C3	−0.00785 (19)	−0.06361 (14)	0.09016 (14)	0.0401 (5)
C4	0.0100 (2)	−0.13289 (15)	0.04369 (16)	0.0507 (6)
H4	−0.0482	−0.1558	0.0015	0.061*
C5	0.1139 (2)	−0.16862 (16)	0.05934 (18)	0.0561 (7)
H5	0.1252	−0.2158	0.0280	0.067*
C6	0.2000 (2)	−0.13502 (15)	0.12040 (17)	0.0501 (6)
H6	0.2689	−0.1608	0.1316	0.060*
C7	0.28236 (19)	−0.02800 (14)	0.22705 (15)	0.0411 (5)
H7	0.3447	−0.0626	0.2401	0.049*
C8	0.3959 (2)	0.06192 (16)	0.32864 (16)	0.0492 (6)
H8A	0.4517	0.0230	0.3198	0.059*
H8B	0.3869	0.0507	0.3846	0.059*
C9	0.4351 (2)	0.15274 (16)	0.32568 (15)	0.0470 (6)
H9A	0.3780	0.1916	0.3323	0.056*
H9B	0.4997	0.1619	0.3731	0.056*
C10	0.5139 (2)	0.26019 (17)	0.24785 (18)	0.0597 (7)
H10A	0.4657	0.3026	0.2622	0.072*
H10B	0.5205	0.2737	0.1916	0.072*
C11	0.6256 (2)	0.26614 (19)	0.31053 (19)	0.0639 (8)
H11A	0.6178	0.2663	0.3672	0.096*
H11B	0.6612	0.3181	0.3009	0.096*
H11C	0.6694	0.2178	0.3035	0.096*
C12	−0.2001 (2)	−0.05535 (18)	0.01591 (16)	0.0537 (7)
H12A	−0.2182	−0.1140	0.0266	0.064*
H12B	−0.1828	−0.0535	−0.0382	0.064*
C13	−0.2952 (2)	0.0027 (2)	0.01422 (19)	0.0710 (8)
H13A	−0.3164	−0.0041	0.0658	0.107*
H13B	−0.3562	−0.0117	−0.0334	0.107*
H13C	−0.2739	0.0611	0.0091	0.107*
C14	0.11326 (18)	0.30877 (14)	0.10555 (14)	0.0389 (5)
C15	0.20996 (17)	0.26120 (13)	0.11291 (13)	0.0355 (5)
C16	0.27758 (19)	0.28547 (15)	0.06010 (14)	0.0410 (5)
C17	0.2535 (2)	0.35687 (16)	0.00929 (16)	0.0551 (7)
H17	0.3005	0.3732	−0.0228	0.066*
C18	0.1593 (2)	0.40514 (18)	0.00539 (17)	0.0599 (7)
H18	0.1442	0.4542	−0.0282	0.072*
C19	0.0899 (2)	0.38012 (16)	0.05081 (16)	0.0514 (6)
H19	0.0252	0.4108	0.0458	0.062*
C20	0.03422 (19)	0.29130 (15)	0.15277 (15)	0.0433 (6)
H20	−0.0242	0.3297	0.1444	0.052*
C21	−0.0571 (2)	0.23231 (17)	0.2451 (2)	0.0602 (7)
H21A	−0.0905	0.2888	0.2372	0.072*
H21B	−0.0267	0.2234	0.3057	0.072*
C22	−0.1456 (2)	0.16612 (18)	0.2113 (2)	0.0644 (8)
H22A	−0.2106	0.1821	0.2286	0.077*
H22B	−0.1654	0.1676	0.1498	0.077*
C23	−0.0843 (3)	0.06135 (19)	0.33260 (18)	0.0655 (8)
H23A	−0.1491	0.0676	0.3531	0.079*
H23B	−0.0307	0.1039	0.3610	0.079*
C24	−0.0368 (3)	−0.0266 (2)	0.3540 (2)	0.0901 (11)
H24A	−0.0897	−0.0688	0.3259	0.135*
H24B	−0.0190	−0.0352	0.4143	0.135*
H24C	0.0288	−0.0322	0.3355	0.135*
C25	0.4284 (2)	0.2466 (2)	0.00521 (18)	0.0654 (8)
H25A	0.4644	0.3021	0.0151	0.078*
H25B	0.3800	0.2458	−0.0522	0.078*
C26	0.5126 (3)	0.1772 (2)	0.0158 (2)	0.0878 (11)
H26A	0.5575	0.1763	0.0735	0.132*
H26B	0.5582	0.1878	−0.0214	0.132*
H26C	0.4762	0.1229	0.0020	0.132*
C27	0.2027 (2)	0.14706 (16)	0.43733 (18)	0.0491 (6)

	U11	U22	U33	U12	U13	U23
Zn1	0.03578 (15)	0.03238 (15)	0.04647 (17)	−0.00390 (11)	0.01557 (12)	−0.00297 (11)
S1	0.0852 (6)	0.1015 (7)	0.0522 (4)	−0.0016 (5)	0.0221 (4)	0.0014 (4)
O1	0.0345 (8)	0.0380 (9)	0.0611 (10)	−0.0048 (7)	0.0202 (8)	−0.0166 (7)
O2	0.0383 (9)	0.0521 (10)	0.0565 (10)	−0.0086 (8)	0.0135 (8)	−0.0118 (8)
O3	0.0348 (8)	0.0423 (9)	0.0514 (9)	0.0036 (7)	0.0148 (7)	0.0109 (7)
O4	0.0447 (10)	0.0605 (11)	0.0526 (10)	0.0014 (8)	0.0205 (8)	0.0112 (8)
O5	0.0583 (12)	0.0506 (13)	0.144 (2)	−0.0014 (10)	0.0361 (13)	−0.0036 (12)
O6	0.0652 (15)	0.1000 (19)	0.208 (3)	−0.0290 (14)	0.0664 (18)	−0.0322 (19)
O7	0.0703 (14)	0.0690 (14)	0.125 (2)	0.0200 (12)	0.0454 (14)	0.0028 (13)
N1	0.0351 (10)	0.0365 (11)	0.0471 (11)	−0.0016 (8)	0.0110 (9)	0.0076 (9)
N2	0.0353 (10)	0.0424 (11)	0.0471 (11)	−0.0054 (9)	0.0057 (9)	0.0008 (9)
N3	0.0396 (11)	0.0345 (11)	0.0600 (13)	−0.0019 (8)	0.0206 (9)	−0.0086 (9)
N4	0.0392 (11)	0.0513 (13)	0.0690 (14)	−0.0087 (9)	0.0301 (10)	−0.0145 (11)
N5	0.0614 (15)	0.0613 (15)	0.0481 (13)	−0.0093 (11)	0.0195 (11)	−0.0086 (11)
N6	0.0469 (13)	0.0566 (15)	0.0828 (17)	−0.0006 (11)	0.0327 (12)	0.0022 (12)
C1	0.0440 (13)	0.0289 (11)	0.0467 (13)	−0.0014 (10)	0.0209 (11)	0.0035 (10)
C2	0.0427 (12)	0.0284 (11)	0.0430 (12)	−0.0046 (9)	0.0237 (10)	−0.0008 (9)
C3	0.0451 (13)	0.0361 (12)	0.0439 (13)	−0.0058 (10)	0.0202 (11)	−0.0015 (10)
C4	0.0641 (17)	0.0418 (14)	0.0480 (14)	−0.0111 (12)	0.0183 (13)	−0.0100 (11)
C5	0.076 (2)	0.0350 (13)	0.0653 (17)	0.0021 (13)	0.0325 (15)	−0.0103 (12)
C6	0.0604 (16)	0.0337 (13)	0.0645 (17)	0.0086 (12)	0.0312 (14)	0.0036 (12)
C7	0.0399 (13)	0.0341 (13)	0.0534 (14)	0.0058 (10)	0.0199 (11)	0.0139 (11)
C8	0.0429 (14)	0.0505 (15)	0.0510 (15)	−0.0021 (11)	0.0072 (12)	0.0097 (12)
C9	0.0403 (13)	0.0503 (15)	0.0463 (14)	−0.0073 (11)	0.0050 (11)	0.0006 (11)
C10	0.0610 (17)	0.0486 (16)	0.0663 (18)	−0.0148 (13)	0.0121 (14)	0.0054 (13)
C11	0.0486 (16)	0.0622 (18)	0.081 (2)	−0.0182 (13)	0.0183 (15)	−0.0178 (15)
C12	0.0517 (15)	0.0602 (17)	0.0445 (14)	−0.0156 (13)	0.0056 (12)	0.0024 (12)
C13	0.0466 (16)	0.096 (2)	0.069 (2)	−0.0077 (16)	0.0136 (14)	0.0072 (17)
C14	0.0402 (13)	0.0331 (12)	0.0389 (12)	−0.0022 (10)	0.0033 (10)	−0.0076 (9)
C15	0.0357 (12)	0.0312 (12)	0.0353 (12)	−0.0056 (9)	0.0026 (9)	−0.0024 (9)
C16	0.0407 (13)	0.0423 (13)	0.0369 (12)	−0.0063 (10)	0.0053 (10)	−0.0010 (10)
C17	0.0661 (18)	0.0554 (16)	0.0433 (14)	−0.0082 (14)	0.0139 (13)	0.0093 (12)
C18	0.0716 (19)	0.0499 (16)	0.0526 (16)	0.0057 (14)	0.0074 (14)	0.0137 (13)
C19	0.0548 (16)	0.0429 (14)	0.0494 (15)	0.0095 (12)	0.0021 (13)	−0.0005 (11)
C20	0.0362 (12)	0.0352 (13)	0.0550 (14)	0.0027 (10)	0.0066 (11)	−0.0122 (11)
C21	0.0563 (16)	0.0442 (15)	0.093 (2)	0.0027 (12)	0.0424 (16)	−0.0065 (14)
C22	0.0434 (15)	0.0602 (18)	0.100 (2)	0.0053 (13)	0.0371 (16)	0.0020 (16)
C23	0.0709 (19)	0.0653 (19)	0.071 (2)	−0.0144 (15)	0.0375 (16)	−0.0140 (15)
C24	0.099 (3)	0.082 (2)	0.097 (3)	−0.001 (2)	0.041 (2)	0.019 (2)
C25	0.0595 (18)	0.083 (2)	0.0630 (18)	−0.0080 (16)	0.0326 (15)	0.0040 (15)
C26	0.080 (2)	0.084 (2)	0.121 (3)	0.002 (2)	0.064 (2)	0.004 (2)
C27	0.0440 (14)	0.0466 (15)	0.0622 (17)	−0.0063 (11)	0.0240 (13)	−0.0089 (12)

Zn1—O1	1.9641 (15)	C9—H9A	0.9700
Zn1—O3	1.9890 (15)	C9—H9B	0.9700
Zn1—N5	2.030 (2)	C10—C11	1.502 (4)
Zn1—N3	2.1305 (19)	C10—H10A	0.9700
Zn1—N1	2.1351 (19)	C10—H10B	0.9700
S1—C27	1.622 (3)	C11—H11A	0.9600
O1—C2	1.316 (2)	C11—H11B	0.9600
O2—C3	1.365 (3)	C11—H11C	0.9600
O2—C12	1.438 (3)	C12—C13	1.497 (4)
O3—C15	1.310 (2)	C12—H12A	0.9700
O4—C16	1.370 (3)	C12—H12B	0.9700
O4—C25	1.432 (3)	C13—H13A	0.9600
O5—N6	1.243 (3)	C13—H13B	0.9600
O6—N6	1.209 (3)	C13—H13C	0.9600
O7—N6	1.223 (3)	C14—C15	1.405 (3)
N1—C7	1.278 (3)	C14—C19	1.408 (3)
N1—C8	1.464 (3)	C14—C20	1.446 (3)
N2—C9	1.477 (3)	C15—C16	1.423 (3)
N2—C10	1.496 (3)	C16—C17	1.373 (3)
N2—H2A	0.9000	C17—C18	1.393 (4)
N2—H2B	0.9000	C17—H17	0.9300
N3—C20	1.271 (3)	C18—C19	1.353 (4)
N3—C21	1.481 (3)	C18—H18	0.9300
N4—C23	1.482 (3)	C19—H19	0.9300
N4—C22	1.488 (3)	C20—H20	0.9300
N4—H4A	0.9000	C21—C22	1.510 (4)
N4—H4B	0.9000	C21—H21A	0.9700
N5—C27	1.149 (3)	C21—H21B	0.9700
C1—C6	1.404 (3)	C22—H22A	0.9700
C1—C2	1.410 (3)	C22—H22B	0.9700
C1—C7	1.441 (3)	C23—C24	1.500 (4)
C2—C3	1.411 (3)	C23—H23A	0.9700
C3—C4	1.375 (3)	C23—H23B	0.9700
C4—C5	1.383 (4)	C24—H24A	0.9600
C4—H4	0.9300	C24—H24B	0.9600
C5—C6	1.363 (4)	C24—H24C	0.9600
C5—H5	0.9300	C25—C26	1.493 (4)
C6—H6	0.9300	C25—H25A	0.9700
C7—H7	0.9300	C25—H25B	0.9700
C8—C9	1.505 (3)	C26—H26A	0.9600
C8—H8A	0.9700	C26—H26B	0.9600
C8—H8B	0.9700	C26—H26C	0.9600
O1—Zn1—O3	118.31 (7)	C10—C11—H11B	109.5
O1—Zn1—N5	113.14 (8)	H11A—C11—H11B	109.5
O3—Zn1—N5	128.40 (8)	C10—C11—H11C	109.5
O1—Zn1—N3	91.66 (7)	H11A—C11—H11C	109.5
O3—Zn1—N3	89.74 (7)	H11B—C11—H11C	109.5
N5—Zn1—N3	92.49 (9)	O2—C12—C13	107.4 (2)
O1—Zn1—N1	87.31 (7)	O2—C12—H12A	110.2
O3—Zn1—N1	87.34 (7)	C13—C12—H12A	110.2
N5—Zn1—N1	91.49 (8)	O2—C12—H12B	110.2
N3—Zn1—N1	175.98 (7)	C13—C12—H12B	110.2
C2—O1—Zn1	127.92 (13)	H12A—C12—H12B	108.5
C3—O2—C12	117.82 (19)	C12—C13—H13A	109.5
C15—O3—Zn1	129.83 (14)	C12—C13—H13B	109.5
C16—O4—C25	117.45 (19)	H13A—C13—H13B	109.5
C7—N1—C8	117.0 (2)	C12—C13—H13C	109.5
C7—N1—Zn1	122.93 (16)	H13A—C13—H13C	109.5
C8—N1—Zn1	120.08 (15)	H13B—C13—H13C	109.5
C9—N2—C10	112.61 (19)	C15—C14—C19	119.8 (2)
C9—N2—H2A	109.1	C15—C14—C20	124.4 (2)
C10—N2—H2A	109.1	C19—C14—C20	115.7 (2)
C9—N2—H2B	109.1	O3—C15—C14	124.2 (2)
C10—N2—H2B	109.1	O3—C15—C16	118.4 (2)
H2A—N2—H2B	107.8	C14—C15—C16	117.3 (2)
C20—N3—C21	115.3 (2)	O4—C16—C17	124.3 (2)
C20—N3—Zn1	123.00 (16)	O4—C16—C15	114.78 (19)
C21—N3—Zn1	121.50 (17)	C17—C16—C15	120.9 (2)
C23—N4—C22	116.4 (2)	C16—C17—C18	120.7 (3)
C23—N4—H4A	108.2	C16—C17—H17	119.7
C22—N4—H4A	108.2	C18—C17—H17	119.7
C23—N4—H4B	108.2	C19—C18—C17	119.5 (2)
C22—N4—H4B	108.2	C19—C18—H18	120.3
H4A—N4—H4B	107.4	C17—C18—H18	120.3
C27—N5—Zn1	163.6 (2)	C18—C19—C14	121.6 (2)
O6—N6—O7	121.5 (3)	C18—C19—H19	119.2
O6—N6—O5	119.9 (2)	C14—C19—H19	119.2
O7—N6—O5	118.6 (2)	N3—C20—C14	128.5 (2)
C6—C1—C2	119.2 (2)	N3—C20—H20	115.7
C6—C1—C7	117.5 (2)	C14—C20—H20	115.7
C2—C1—C7	123.3 (2)	N3—C21—C22	114.1 (2)
O1—C2—C1	123.1 (2)	N3—C21—H21A	108.7
O1—C2—C3	118.5 (2)	C22—C21—H21A	108.7
C1—C2—C3	118.4 (2)	N3—C21—H21B	108.7
O2—C3—C4	125.2 (2)	C22—C21—H21B	108.7
O2—C3—C2	114.18 (19)	H21A—C21—H21B	107.6
C4—C3—C2	120.6 (2)	N4—C22—C21	115.1 (2)
C3—C4—C5	120.3 (2)	N4—C22—H22A	108.5
C3—C4—H4	119.8	C21—C22—H22A	108.5
C5—C4—H4	119.8	N4—C22—H22B	108.5
C6—C5—C4	120.3 (2)	C21—C22—H22B	108.5
C6—C5—H5	119.8	H22A—C22—H22B	107.5
C4—C5—H5	119.8	N4—C23—C24	111.2 (2)
C5—C6—C1	121.0 (2)	N4—C23—H23A	109.4
C5—C6—H6	119.5	C24—C23—H23A	109.4
C1—C6—H6	119.5	N4—C23—H23B	109.4
N1—C7—C1	127.2 (2)	C24—C23—H23B	109.4
N1—C7—H7	116.4	H23A—C23—H23B	108.0
C1—C7—H7	116.4	C23—C24—H24A	109.5
N1—C8—C9	112.99 (19)	C23—C24—H24B	109.5
N1—C8—H8A	109.0	H24A—C24—H24B	109.5
C9—C8—H8A	109.0	C23—C24—H24C	109.5
N1—C8—H8B	109.0	H24A—C24—H24C	109.5
C9—C8—H8B	109.0	H24B—C24—H24C	109.5
H8A—C8—H8B	107.8	O4—C25—C26	108.6 (2)
N2—C9—C8	113.2 (2)	O4—C25—H25A	110.0
N2—C9—H9A	108.9	C26—C25—H25A	110.0
C8—C9—H9A	108.9	O4—C25—H25B	110.0
N2—C9—H9B	108.9	C26—C25—H25B	110.0
C8—C9—H9B	108.9	H25A—C25—H25B	108.4
H9A—C9—H9B	107.8	C25—C26—H26A	109.5
N2—C10—C11	112.9 (2)	C25—C26—H26B	109.5
N2—C10—H10A	109.0	H26A—C26—H26B	109.5
C11—C10—H10A	109.0	C25—C26—H26C	109.5
N2—C10—H10B	109.0	H26A—C26—H26C	109.5
C11—C10—H10B	109.0	H26B—C26—H26C	109.5
H10A—C10—H10B	107.8	N5—C27—S1	179.6 (3)
C10—C11—H11A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O5	0.90	1.96	2.843 (3)	166
N2—H2A···O3	0.90	1.98	2.772 (2)	146
N2—H2A···O4	0.90	2.37	3.022 (3)	129
N4—H4A···O7i	0.90	2.22	3.050 (3)	153
N4—H4A···O5i	0.90	2.50	3.080 (3)	122
N4—H4B···O1	0.90	1.71	2.606 (2)	171
N4—H4B···O2	0.90	2.55	3.051 (3)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O5	0.90	1.96	2.843 (3)	166
N2—H2A⋯O3	0.90	1.98	2.772 (2)	146
N2—H2A⋯O4	0.90	2.37	3.022 (3)	129
N4—H4A⋯O7i	0.90	2.22	3.050 (3)	153
N4—H4A⋯O5i	0.90	2.50	3.080 (3)	122
N4—H4B⋯O1	0.90	1.71	2.606 (2)	171
N4—H4B⋯O2	0.90	2.55	3.051 (3)	116

Symmetry code: (i) .