4-Amino-5-methyl-1,2,4-triazole-3-thione derivative of 4-[2-(2-hydroxy­ethyl)­methyl­amino]­benz­aldehyde

The title compound, 4-{4-[2-(2-hydroxy­ethyl)­methyl­amino]­benzyl­idene­amino}-5-methyl-1,2,4-triazole-3-thione, C₁₃H₁₇N₅OS, is present in a thio­ketone form and the triazole ring is almost planar. The asymmetric unit consists of two mol­ecules which have different conformations. There is a weak C—H...S intramolecular interaction, a weak O—H...S intermolecular interaction and intermolecular N—H...O and O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.146
• Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found



ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

4-{4-[2-(2-hydroxyethyl)methylamino]benzylideneamino}-5-methyl- 1,2,4-triazole-3-thione

Crystal data

C13H17N5OS	F(000) = 616
Mr = 291.38	Dx = 1.352 Mg m^−3
Triclinic, P1	Melting point: 448.6 K
a = 10.7043 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7230 (2) Å	Cell parameters from 4869 reflections
c = 13.9487 (3) Å	θ = 1.6–28.3°
α = 103.352 (1)°	µ = 0.23 mm^−1
β = 111.835 (1)°	T = 293 K
γ = 92.519 (1)°	Plate, light yellow
V = 1431.01 (5) Å^3	0.40 × 0.28 × 0.06 mm
Z = 4

Data collection

Siemens SMART CCD area-aetector diffractometer	4863 independent reflections
Radiation source: fine-focus sealed tube	3249 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 1.6°
ω scans	h = −8→12
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −12→10
Tmin = 0.914, Tmax = 0.986	l = −16→16
7981 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0734P)^2] where P = (Fo^2 + 2Fc^2)/3
4863 reflections	(Δ/σ)max = 0.001
373 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0,88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 4.023 cm and the detector swing angle was -35°. Coverage of the unit set is 91% complete. Crystal decay was monitored by SAINT (Siemens, 1996) and was found to be negligible.

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 (Ų)

	x	y	z	Uiso*/Ueq
S1A	0.69145 (7)	0.69502 (8)	0.72016 (6)	0.0527 (2)
O1A	0.0703 (2)	0.66841 (19)	−0.05338 (14)	0.0466 (5)
N1A	0.9506 (2)	0.8044 (2)	0.79000 (16)	0.0448 (6)
H1AA	0.9771	0.7673	0.8412	0.054*
N3A	0.8274 (2)	0.8632 (2)	0.65341 (15)	0.0367 (5)
N4A	0.7339 (2)	0.8770 (2)	0.55563 (16)	0.0416 (5)
N5A	0.2095 (2)	0.8870 (2)	0.13868 (17)	0.0468 (6)
N2A	1.0380 (2)	0.8868 (2)	0.77290 (17)	0.0462 (6)
C1A	1.0061 (3)	1.0107 (3)	0.6388 (2)	0.0548 (8)
H1AB	1.0979	1.0505	0.6837	0.082*
H1AC	0.9480	1.0764	0.6297	0.082*
H1AD	1.0023	0.9631	0.5701	0.082*
C2A	0.9604 (3)	0.9215 (3)	0.6893 (2)	0.0396 (6)
C3A	0.8207 (3)	0.7870 (2)	0.72023 (19)	0.0380 (6)
C4A	0.6090 (3)	0.8385 (3)	0.5280 (2)	0.0432 (7)
H4AA	0.5806	0.8039	0.5730	0.052*
C5A	0.5090 (3)	0.8482 (2)	0.4255 (2)	0.0389 (6)
C6A	0.3733 (3)	0.8004 (3)	0.3942 (2)	0.0449 (7)
H6AA	0.3479	0.7614	0.4385	0.054*
C7A	0.2744 (3)	0.8092 (3)	0.2985 (2)	0.0439 (7)
H7AA	0.1848	0.7734	0.2789	0.053*
C8A	0.3072 (3)	0.8709 (2)	0.23119 (19)	0.0379 (6)
C9A	0.4452 (3)	0.9178 (3)	0.2627 (2)	0.0439 (7)
H9AA	0.4713	0.9577	0.2191	0.053*
C10A	0.5424 (3)	0.9058 (3)	0.3567 (2)	0.0444 (7)
H10A	0.6329	0.9371	0.3748	0.053*
C11A	0.0683 (3)	0.8309 (3)	0.1005 (2)	0.0491 (7)
H11A	0.0121	0.8797	0.0547	0.059*
H11B	0.0431	0.8399	0.1615	0.059*
C12A	0.0381 (3)	0.6901 (3)	0.0393 (2)	0.0490 (7)
H12A	0.0900	0.6401	0.0861	0.059*
H12B	−0.0577	0.6597	0.0173	0.059*
C13A	0.2454 (3)	0.9634 (3)	0.0766 (2)	0.0532 (8)
H13A	0.2852	1.0494	0.1212	0.080*
H13B	0.1651	0.9676	0.0170	0.080*
H13C	0.3095	0.9238	0.0508	0.080*
S1B	1.28467 (8)	0.16528 (9)	0.92159 (7)	0.0663 (3)
O1B	0.6498 (2)	0.1485 (2)	0.16659 (16)	0.0638 (6)
N1B	1.5501 (2)	0.2721 (2)	1.00488 (17)	0.0444 (6)
H1BA	1.5738	0.2353	1.0564	0.053*
N2B	1.6408 (2)	0.3501 (2)	0.98786 (17)	0.0438 (6)
N3B	1.4323 (2)	0.3373 (2)	0.87137 (15)	0.0369 (5)
N4B	1.3312 (2)	0.3451 (2)	0.77424 (16)	0.0407 (5)
N5B	0.7576 (2)	0.4000 (2)	0.42453 (18)	0.0510 (6)
C1B	1.6141 (3)	0.4734 (3)	0.8523 (2)	0.0546 (8)
H1BB	1.7113	0.4944	0.8868	0.082*
H1BC	1.5737	0.5515	0.8581	0.082*
H1BD	1.5888	0.4296	0.7781	0.082*
C2B	1.5655 (3)	0.3879 (3)	0.9047 (2)	0.0385 (6)
C3B	1.4214 (3)	0.2585 (3)	0.9339 (2)	0.0408 (6)
C4B	1.2201 (2)	0.3737 (2)	0.7832 (2)	0.0365 (6)
H4BA	1.2163	0.3938	0.8505	0.044*
C5B	1.1004 (2)	0.3753 (2)	0.6900 (2)	0.0351 (6)
C6B	0.9942 (3)	0.4377 (3)	0.7029 (2)	0.0404 (6)
H6BA	0.9995	0.4744	0.7719	0.049*
C7B	0.8813 (3)	0.4465 (3)	0.6165 (2)	0.0416 (6)
H7BA	0.8130	0.4905	0.6279	0.050*
C8B	0.8687 (2)	0.3899 (2)	0.5116 (2)	0.0390 (6)
C9B	0.9744 (3)	0.3230 (3)	0.4989 (2)	0.0437 (7)
H9BA	0.9677	0.2820	0.4304	0.052*
C10B	1.0866 (3)	0.3174 (2)	0.5856 (2)	0.0403 (6)
H10B	1.1554	0.2738	0.5747	0.048*
C11B	0.7401 (3)	0.3393 (3)	0.3140 (2)	0.0516 (8)
H11C	0.8284	0.3417	0.3095	0.062*
H11D	0.6858	0.3883	0.2674	0.062*
C12B	0.6721 (3)	0.2012 (3)	0.2762 (2)	0.0499 (7)
H12C	0.7290	0.1503	0.3195	0.060*
H12D	0.5858	0.1976	0.2841	0.060*
C13B	0.6554 (3)	0.4782 (3)	0.4401 (3)	0.0634 (9)
H13E	0.6992	0.5624	0.4865	0.095*
H13F	0.6056	0.4370	0.4719	0.095*
H13G	0.5940	0.4868	0.3721	0.095*
H1AE	0.159 (4)	0.666 (4)	−0.039 (3)	0.100 (14)*
H1BE	0.695 (6)	0.083 (6)	0.155 (5)	0.21 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0453 (5)	0.0619 (5)	0.0566 (5)	0.0056 (3)	0.0192 (4)	0.0282 (4)
O1A	0.0347 (12)	0.0619 (12)	0.0345 (10)	0.0090 (9)	0.0045 (8)	0.0120 (9)
N1A	0.0418 (14)	0.0569 (14)	0.0328 (12)	0.0039 (11)	0.0068 (10)	0.0203 (11)
N3A	0.0385 (13)	0.0426 (12)	0.0271 (11)	0.0085 (10)	0.0081 (9)	0.0133 (9)
N4A	0.0427 (15)	0.0466 (13)	0.0302 (12)	0.0073 (10)	0.0058 (10)	0.0146 (10)
N5A	0.0462 (15)	0.0496 (14)	0.0359 (13)	0.0017 (11)	0.0032 (10)	0.0180 (11)
N2A	0.0416 (14)	0.0529 (14)	0.0394 (13)	0.0005 (11)	0.0099 (11)	0.0146 (11)
C1A	0.0558 (19)	0.0604 (18)	0.0485 (18)	−0.0009 (14)	0.0182 (14)	0.0209 (15)
C2A	0.0404 (16)	0.0438 (15)	0.0313 (14)	0.0030 (12)	0.0113 (12)	0.0090 (12)
C3A	0.0407 (16)	0.0407 (14)	0.0308 (13)	0.0106 (11)	0.0111 (12)	0.0100 (11)
C4A	0.0438 (18)	0.0484 (16)	0.0359 (15)	0.0083 (13)	0.0118 (12)	0.0147 (12)
C5A	0.0399 (16)	0.0412 (14)	0.0315 (14)	0.0067 (12)	0.0074 (11)	0.0134 (11)
C6A	0.0452 (18)	0.0514 (16)	0.0399 (15)	0.0066 (13)	0.0123 (13)	0.0231 (13)
C7A	0.0365 (16)	0.0507 (16)	0.0414 (15)	0.0023 (12)	0.0089 (12)	0.0181 (13)
C8A	0.0392 (16)	0.0351 (14)	0.0320 (14)	0.0048 (11)	0.0061 (12)	0.0083 (11)
C9A	0.0475 (18)	0.0472 (16)	0.0335 (14)	−0.0006 (13)	0.0104 (12)	0.0148 (12)
C10A	0.0384 (16)	0.0486 (16)	0.0401 (15)	0.0006 (12)	0.0090 (12)	0.0125 (13)
C11A	0.0413 (18)	0.0633 (18)	0.0389 (15)	0.0159 (14)	0.0095 (13)	0.0155 (14)
C12A	0.0401 (17)	0.0605 (18)	0.0406 (16)	0.0007 (13)	0.0102 (13)	0.0134 (14)
C13A	0.067 (2)	0.0492 (17)	0.0388 (16)	0.0110 (14)	0.0109 (14)	0.0203 (14)
S1B	0.0406 (5)	0.0849 (6)	0.0817 (6)	0.0036 (4)	0.0154 (4)	0.0534 (5)
O1B	0.0783 (16)	0.0664 (15)	0.0358 (12)	0.0288 (12)	0.0065 (10)	0.0167 (10)
N1B	0.0327 (13)	0.0625 (15)	0.0391 (13)	0.0110 (11)	0.0078 (10)	0.0255 (11)
N2B	0.0333 (13)	0.0509 (14)	0.0420 (13)	0.0077 (10)	0.0071 (10)	0.0154 (11)
N3B	0.0282 (12)	0.0485 (13)	0.0315 (11)	0.0074 (9)	0.0034 (9)	0.0196 (10)
N4B	0.0298 (13)	0.0522 (13)	0.0355 (12)	0.0078 (10)	0.0031 (9)	0.0193 (10)
N5B	0.0411 (14)	0.0519 (14)	0.0417 (14)	0.0128 (11)	−0.0040 (10)	0.0113 (11)
C1B	0.0411 (18)	0.0603 (19)	0.065 (2)	0.0050 (14)	0.0150 (15)	0.0315 (16)
C2B	0.0307 (15)	0.0435 (15)	0.0388 (15)	0.0065 (11)	0.0098 (12)	0.0123 (12)
C3B	0.0360 (16)	0.0504 (16)	0.0361 (15)	0.0128 (12)	0.0080 (12)	0.0209 (12)
C4B	0.0323 (15)	0.0369 (14)	0.0363 (14)	0.0052 (11)	0.0063 (11)	0.0142 (11)
C5B	0.0281 (14)	0.0355 (13)	0.0372 (14)	0.0031 (11)	0.0046 (11)	0.0157 (11)
C6B	0.0359 (16)	0.0442 (15)	0.0373 (15)	0.0060 (12)	0.0097 (12)	0.0114 (12)
C7B	0.0307 (15)	0.0444 (15)	0.0465 (16)	0.0110 (11)	0.0087 (12)	0.0160 (13)
C8B	0.0276 (15)	0.0370 (13)	0.0412 (15)	0.0019 (11)	−0.0002 (11)	0.0129 (12)
C9B	0.0401 (16)	0.0483 (16)	0.0335 (14)	0.0078 (12)	0.0047 (12)	0.0099 (12)
C10B	0.0325 (15)	0.0436 (15)	0.0409 (15)	0.0091 (11)	0.0086 (12)	0.0130 (12)
C11B	0.0415 (17)	0.0570 (18)	0.0476 (18)	0.0020 (13)	0.0007 (13)	0.0272 (14)
C12B	0.0471 (18)	0.0550 (18)	0.0413 (16)	0.0033 (13)	0.0094 (13)	0.0152 (14)
C13B	0.0422 (19)	0.067 (2)	0.065 (2)	0.0174 (15)	−0.0002 (15)	0.0204 (17)

Geometric parameters (Å, º)

S1A—C3A	1.663 (3)	S1B—C3B	1.666 (3)
O1A—C12A	1.430 (3)	O1B—C12B	1.425 (3)
O1A—H1AE	0.90 (4)	O1B—H1BE	0.89 (6)
N1A—C3A	1.342 (3)	N1B—C3B	1.342 (3)
N1A—N2A	1.380 (3)	N1B—N2B	1.375 (3)
N1A—H1AA	0.8600	N1B—H1BA	0.8600
N3A—C2A	1.384 (3)	N2B—C2B	1.308 (3)
N3A—C3A	1.392 (3)	N3B—C2B	1.366 (3)
N3A—N4A	1.405 (3)	N3B—C3B	1.378 (3)
N4A—C4A	1.266 (3)	N3B—N4B	1.408 (3)
N5A—C8A	1.380 (3)	N4B—C4B	1.283 (3)
N5A—C11A	1.450 (3)	N5B—C8B	1.378 (3)
N5A—C13A	1.454 (3)	N5B—C13B	1.456 (4)
N2A—C2A	1.302 (3)	N5B—C11B	1.465 (3)
C1A—C2A	1.475 (4)	C1B—C2B	1.481 (4)
C1A—H1AB	0.9600	C1B—H1BB	0.9600
C1A—H1AC	0.9600	C1B—H1BC	0.9600
C1A—H1AD	0.9600	C1B—H1BD	0.9600
C4A—C5A	1.462 (4)	C4B—C5B	1.451 (3)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.386 (4)	C5B—C6B	1.392 (3)
C5A—C10A	1.393 (4)	C5B—C10B	1.393 (3)
C6A—C7A	1.388 (4)	C6B—C7B	1.379 (3)
C6A—H6AA	0.9300	C6B—H6BA	0.9300
C7A—C8A	1.399 (4)	C7B—C8B	1.401 (4)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.406 (4)	C8B—C9B	1.410 (4)
C9A—C10A	1.376 (4)	C9B—C10B	1.367 (3)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.507 (4)	C11B—C12B	1.504 (4)
C11A—H11A	0.9700	C11B—H11C	0.9700
C11A—H11B	0.9700	C11B—H11D	0.9700
C12A—H12A	0.9700	C12B—H12C	0.9700
C12A—H12B	0.9700	C12B—H12D	0.9700
C13A—H13A	0.9600	C13B—H13E	0.9600
C13A—H13B	0.9600	C13B—H13F	0.9600
C13A—H13C	0.9600	C13B—H13G	0.9600
C12A—O1A—H1AE	114 (2)	C12B—O1B—H1BE	115 (4)
C3A—N1A—N2A	114.5 (2)	C3B—N1B—N2B	113.9 (2)
C3A—N1A—H1AA	122.7	C3B—N1B—H1BA	123.0
N2A—N1A—H1AA	122.7	N2B—N1B—H1BA	123.0
C2A—N3A—C3A	108.6 (2)	C2B—N2B—N1B	104.1 (2)
C2A—N3A—N4A	117.8 (2)	C2B—N3B—C3B	109.4 (2)
C3A—N3A—N4A	133.0 (2)	C2B—N3B—N4B	122.8 (2)
C4A—N4A—N3A	118.8 (2)	C3B—N3B—N4B	126.5 (2)
C8A—N5A—C11A	121.9 (2)	C4B—N4B—N3B	113.0 (2)
C8A—N5A—C13A	120.5 (2)	C8B—N5B—C13B	120.2 (2)
C11A—N5A—C13A	117.6 (2)	C8B—N5B—C11B	122.3 (2)
C2A—N2A—N1A	104.1 (2)	C13B—N5B—C11B	117.4 (2)
C2A—C1A—H1AB	109.5	C2B—C1B—H1BB	109.5
C2A—C1A—H1AC	109.5	C2B—C1B—H1BC	109.5
H1AB—C1A—H1AC	109.5	H1BB—C1B—H1BC	109.5
C2A—C1A—H1AD	109.5	C2B—C1B—H1BD	109.5
H1AB—C1A—H1AD	109.5	H1BB—C1B—H1BD	109.5
H1AC—C1A—H1AD	109.5	H1BC—C1B—H1BD	109.5
N2A—C2A—N3A	110.7 (2)	N2B—C2B—N3B	110.2 (2)
N2A—C2A—C1A	125.3 (3)	N2B—C2B—C1B	126.2 (2)
N3A—C2A—C1A	124.0 (2)	N3B—C2B—C1B	123.6 (2)
N1A—C3A—N3A	102.1 (2)	N1B—C3B—N3B	102.2 (2)
N1A—C3A—S1A	126.1 (2)	N1B—C3B—S1B	128.8 (2)
N3A—C3A—S1A	131.81 (19)	N3B—C3B—S1B	128.90 (19)
N4A—C4A—C5A	120.4 (2)	N4B—C4B—C5B	121.0 (2)
N4A—C4A—H4AA	119.8	N4B—C4B—H4BA	119.5
C5A—C4A—H4AA	119.8	C5B—C4B—H4BA	119.5
C6A—C5A—C10A	117.1 (2)	C6B—C5B—C10B	117.4 (2)
C6A—C5A—C4A	119.7 (2)	C6B—C5B—C4B	119.9 (2)
C10A—C5A—C4A	123.2 (2)	C10B—C5B—C4B	122.7 (2)
C5A—C6A—C7A	121.8 (3)	C7B—C6B—C5B	121.9 (2)
C5A—C6A—H6AA	119.1	C7B—C6B—H6BA	119.1
C7A—C6A—H6AA	119.1	C5B—C6B—H6BA	119.1
C6A—C7A—C8A	121.1 (2)	C6B—C7B—C8B	120.6 (2)
C6A—C7A—H7AA	119.5	C6B—C7B—H7BA	119.7
C8A—C7A—H7AA	119.5	C8B—C7B—H7BA	119.7
N5A—C8A—C7A	122.1 (2)	N5B—C8B—C7B	121.2 (2)
N5A—C8A—C9A	121.0 (2)	N5B—C8B—C9B	121.5 (2)
C7A—C8A—C9A	116.9 (2)	C7B—C8B—C9B	117.3 (2)
C10A—C9A—C8A	121.2 (3)	C10B—C9B—C8B	121.2 (2)
C10A—C9A—H9AA	119.4	C10B—C9B—H9BA	119.4
C8A—C9A—H9AA	119.4	C8B—C9B—H9BA	119.4
C9A—C10A—C5A	121.8 (3)	C9B—C10B—C5B	121.6 (2)
C9A—C10A—H10A	119.1	C9B—C10B—H10B	119.2
C5A—C10A—H10A	119.1	C5B—C10B—H10B	119.2
N5A—C11A—C12A	114.2 (2)	N5B—C11B—C12B	111.8 (2)
N5A—C11A—H11A	108.7	N5B—C11B—H11C	109.2
C12A—C11A—H11A	108.7	C12B—C11B—H11C	109.2
N5A—C11A—H11B	108.7	N5B—C11B—H11D	109.2
C12A—C11A—H11B	108.7	C12B—C11B—H11D	109.2
H11A—C11A—H11B	107.6	H11C—C11B—H11D	107.9
O1A—C12A—C11A	112.4 (2)	O1B—C12B—C11B	110.0 (2)
O1A—C12A—H12A	109.1	O1B—C12B—H12C	109.7
C11A—C12A—H12A	109.1	C11B—C12B—H12C	109.7
O1A—C12A—H12B	109.1	O1B—C12B—H12D	109.7
C11A—C12A—H12B	109.1	C11B—C12B—H12D	109.7
H12A—C12A—H12B	107.9	H12C—C12B—H12D	108.2
N5A—C13A—H13A	109.5	N5B—C13B—H13E	109.5
N5A—C13A—H13B	109.5	N5B—C13B—H13F	109.5
H13A—C13A—H13B	109.5	H13E—C13B—H13F	109.5
N5A—C13A—H13C	109.5	N5B—C13B—H13G	109.5
H13A—C13A—H13C	109.5	H13E—C13B—H13G	109.5
H13B—C13A—H13C	109.5	H13F—C13B—H13G	109.5
C2A—N3A—N4A—C4A	−171.3 (2)	C3B—N1B—N2B—C2B	1.0 (3)
C3A—N3A—N4A—C4A	18.4 (4)	C2B—N3B—N4B—C4B	−137.4 (2)
C3A—N1A—N2A—C2A	−0.3 (3)	C3B—N3B—N4B—C4B	57.1 (3)
N1A—N2A—C2A—N3A	−0.2 (3)	N1B—N2B—C2B—N3B	0.8 (3)
N1A—N2A—C2A—C1A	179.8 (3)	N1B—N2B—C2B—C1B	−179.4 (3)
C3A—N3A—C2A—N2A	0.7 (3)	C3B—N3B—C2B—N2B	−2.4 (3)
N4A—N3A—C2A—N2A	−171.9 (2)	N4B—N3B—C2B—N2B	−170.1 (2)
C3A—N3A—C2A—C1A	−179.3 (2)	C3B—N3B—C2B—C1B	177.8 (2)
N4A—N3A—C2A—C1A	8.2 (4)	N4B—N3B—C2B—C1B	10.1 (4)
N2A—N1A—C3A—N3A	0.7 (3)	N2B—N1B—C3B—N3B	−2.4 (3)
N2A—N1A—C3A—S1A	−179.46 (19)	N2B—N1B—C3B—S1B	175.3 (2)
C2A—N3A—C3A—N1A	−0.8 (3)	C2B—N3B—C3B—N1B	2.8 (3)
N4A—N3A—C3A—N1A	170.2 (2)	N4B—N3B—C3B—N1B	169.9 (2)
C2A—N3A—C3A—S1A	179.4 (2)	C2B—N3B—C3B—S1B	−174.9 (2)
N4A—N3A—C3A—S1A	−9.6 (4)	N4B—N3B—C3B—S1B	−7.9 (4)
N3A—N4A—C4A—C5A	−178.4 (2)	N3B—N4B—C4B—C5B	−174.7 (2)
N4A—C4A—C5A—C6A	177.2 (2)	N4B—C4B—C5B—C6B	−163.4 (2)
N4A—C4A—C5A—C10A	−4.0 (4)	N4B—C4B—C5B—C10B	16.0 (4)
C10A—C5A—C6A—C7A	0.0 (4)	C10B—C5B—C6B—C7B	−2.3 (4)
C4A—C5A—C6A—C7A	179.0 (3)	C4B—C5B—C6B—C7B	177.1 (2)
C5A—C6A—C7A—C8A	−2.2 (4)	C5B—C6B—C7B—C8B	1.4 (4)
C11A—N5A—C8A—C7A	−5.6 (4)	C13B—N5B—C8B—C7B	4.5 (4)
C13A—N5A—C8A—C7A	173.5 (2)	C11B—N5B—C8B—C7B	−178.6 (2)
C11A—N5A—C8A—C9A	175.2 (2)	C13B—N5B—C8B—C9B	−175.1 (3)
C13A—N5A—C8A—C9A	−5.7 (4)	C11B—N5B—C8B—C9B	1.8 (4)
C6A—C7A—C8A—N5A	−176.4 (2)	C6B—C7B—C8B—N5B	−178.9 (3)
C6A—C7A—C8A—C9A	2.8 (4)	C6B—C7B—C8B—C9B	0.8 (4)
N5A—C8A—C9A—C10A	177.8 (3)	N5B—C8B—C9B—C10B	177.6 (3)
C7A—C8A—C9A—C10A	−1.5 (4)	C7B—C8B—C9B—C10B	−2.0 (4)
C8A—C9A—C10A—C5A	−0.6 (4)	C8B—C9B—C10B—C5B	1.1 (4)
C6A—C5A—C10A—C9A	1.4 (4)	C6B—C5B—C10B—C9B	1.1 (4)
C4A—C5A—C10A—C9A	−177.5 (3)	C4B—C5B—C10B—C9B	−178.3 (3)
C8A—N5A—C11A—C12A	−81.4 (3)	C8B—N5B—C11B—C12B	86.3 (3)
C13A—N5A—C11A—C12A	99.5 (3)	C13B—N5B—C11B—C12B	−96.7 (3)
N5A—C11A—C12A—O1A	−59.4 (3)	N5B—C11B—C12B—O1B	176.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···O1A^i	0.86	2.00	2.845 (3)	167
N1B—H1BA···O1B^i	0.86	1.92	2.775 (3)	172
O1A—H1AE···N2B^ii	0.90 (5)	2.02 (4)	2.911 (3)	171 (4)
O1B—H1BE···S1B^iii	0.89 (7)	2.68 (7)	3.502 (2)	154 (6)
C4A—H4AA···S1A	0.93	2.53	3.255 (3)	135
C4B—H4BA···S1B	0.93	2.87	3.215 (3)	103

Symmetry codes: (i) x+1, y, z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+2, −y, −z+1.