2-Amino-4,5-dihydro-1H-imidazol-3-ium 7,8-dihydro­imidazo[1,2-c][1,3,5]thiadiazine-2,4(6H)-dithione(1−) dimethyl­formamide disolvate

The structure of the title compound, C₅H₄N₃S₃⁻·C₃H₈N₃⁺·2C₃H₇NO, has been determined from a non-merohedral twin. The asymmetric unit consists of a heterocyclic anion, a guanidinium-type cation and two dimethyl­formamide solvent mol­ecules. The three C—N bond lengths in the guanidinium fragment range from 1.315 (3) to 1.342 (3) Å, the shortest bond being to the exocyclic amino group. The anion and cation are connected via a pair of N—H...N hydrogen bonds and the two solvent mol­ecules are linked to this ion pair via N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.088
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93

Author Response: The structure was solved and refined for a nonmerohedral twin. 250 partially overlapping reflections were removed from the data set and they are the cause of low completness

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           26.50
           From the CIF: _diffrn_reflns_theta_full          26.50
           From the CIF: _reflns_number_total               4006
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         4335
           Completeness (_total/calc)             92.41%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.92
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        700 Deg.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C2D
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C3D
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         19
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C5 H4 N3 S3

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

In course of our research on the reactivity of 2-hydroxylamino-4,5-dihydroimidazolium-O-sulfonate, it was reacted with carbon disulfide in aqueous NaOH, forming, unexpectedly, the salt of 2-aminoimidazoline and 7,8-dihydroimidazo [1,2-c][1,3,5]thiadiazine-2,4(6H)-dithione (Saczewski et al., 2003). The crystal structure of (I) has been solved based on diffraction data collected for a twinned specimen. The structure was refined to a R1 factor = 0.20 but twinning was not taken into account, neither at the data processing stage nor during refinement. The structure just served to confirm the connectivity of atoms deduced from spectroscopic methods. When we noticed that this is the first crystal structure of a 2-aminoimdazoline in the Cambridge Structural Databank (Allen, 2002) we decided to refine this structure taking twinning into account. Here, we present the structure of (I) refined as a nonmerohedral twin.

The asymmetric unit is shown in Fig. 1. The cation and anion are linked via two N—H···N hydrogen bonds into an ionic pair and the two solvate molecule are joined via N—H···O interactions to the cation, thus forming discrete hydrogen-bonded assemblies. The five-membered ring of the 2-aminoimidazolinium cation, with the largest endocyclic torsion angle of 15.8 (2)°, forms a slightly puckered half-chair. The three C—N bonds of the guanidinium fragment in the cation range from 1.315 (3) to 1.342 (3) Å, with the shortest bond being to the exocyclic amino group and the longest to the ring N3 atom exhibiting slightly pyramidal sp² hybridization. Deprotonation has an enormous influence on the geometry of the 7,8-dihydroimidazo[1,2-c][1,3,5]thiadiazine-2,4(6H)dithione molecule. For example, in the neutral form, with the acidic proton bonded to N7A (Saczewski et al., 2003), the endocyclic bond angle at this atom is 113.72(16.)° whereas in the ionic form this angle is much smaller, 108.93 (17)°. Bond lengths are also strongly altered and, for example, the N1A—C6A bond length changes from 1.323 (2) in the neutral acid to 1.373 (3) Å in the anion.

Related literature

For synthesis and other data for the title compound see Saczewski et al. (2003). For related literature, see: Allen (2002); Cooper et al. (2002); Farrugia (1999).

S2. Experimental

The title compound was prepared according to the known procedure (Saczewski et al., 2003). Crystals for X-ray analysis were obtained by recrystallization from a dimethylformamide solution of (I).

S3. Refinement

The twin matrix, 1 0 0 0.475 - 1 0 0.003 0 - 1, corresponding to 180° rotation about [100] direct lattice direction has been determined with the program ROTAX (Cooper et al., 2002). For the refinement with the SHELXL97 program (Sheldrick, 1997), the reflection data file was prepared in the HKLF 5 format using the 'Make HKLF5' function of the WinGX program (Farrugia, 1999). The overlapping reflections and those belonging to only one twin domain are used in the refinement (HKLF 5 format of SHELXL). Those which were excluded, 250 reflections, are partial overlaps which could not be integrated properly at the data processing stage.

The H atoms of the N—H groups were freely refined. The H atoms bonded to C atoms were placed at calculated positions, with C—H = 0.95–0.99 Å, and refined as riding on their parent atoms, with U_iso(H) = x U_eq(C), where x = 1.5 for the H atoms from methyl groups and x = 1.2 for the remaining H atoms.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation (Siemens, 1989) and Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Asymmetric unit of (I) showing atom labelling scheme and displacement ellipsoids shown at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Crystal packing shown down the a-axis. Hydrogen bonds are shown as dashed lines.

2-Amino-4,5-dihydro-1H-imidazol-3-ium 7,8-dihydroimidazo[1,2-c][1,3,5]thiadiazine-2,4(6H)-dithione(1-) dimethylformamide disolvate

Crystal data

C3H8N3^+·C5H4N3S3^−·2C3H7NO	Z = 2
Mr = 434.61	F(000) = 460
Triclinic, P1	Dx = 1.383 Mg m^−3
Hall symbol: -P 1	Melting point: 447 K
a = 6.8301 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.1321 (14) Å	Cell parameters from 2455 reflections
c = 12.9487 (10) Å	θ = 4.0–25.0°
α = 79.232 (7)°	µ = 0.38 mm^−1
β = 89.907 (7)°	T = 120 K
γ = 82.125 (7)°	Prism, yellow
V = 1043.82 (18) Å^3	0.60 × 0.20 × 0.10 mm

Data collection

Kuma KM-4-CCD κ-geometry diffractometer	3627 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 26.5°, θmin = 4.2°
ω scans	h = −8→8
8801 measured reflections	k = −15→15
4006 independent reflections	l = −16→16

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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F^2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0351P)^2 + 0.3779P] where P = (Fo^2 + 2Fc^2)/3
4006 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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	0.74388 (10)	−0.03696 (5)	0.69870 (4)	0.02750 (15)
S2A	0.73548 (10)	−0.34589 (5)	1.09680 (5)	0.02675 (15)
N1A	0.7458 (3)	0.01169 (14)	0.88951 (13)	0.0205 (4)
C2A	0.7457 (3)	−0.06552 (17)	0.83134 (16)	0.0194 (4)
S3A	0.74710 (10)	−0.21218 (4)	0.88413 (4)	0.02568 (15)
C4A	0.7430 (3)	−0.22047 (17)	1.02092 (17)	0.0199 (5)
N5A	0.7464 (3)	−0.12406 (14)	1.05684 (13)	0.0192 (4)
C6A	0.7493 (3)	−0.01300 (17)	0.99742 (16)	0.0190 (4)
N7A	0.7534 (3)	0.06311 (14)	1.05371 (13)	0.0224 (4)
C8A	0.7578 (4)	0.00908 (18)	1.16541 (16)	0.0222 (5)
H8B	0.6442	0.0435	1.2016	0.027*
H8A	0.8815	0.0187	1.2004	0.027*
C9A	0.7465 (4)	−0.11769 (17)	1.16928 (16)	0.0224 (5)
H9B	0.8624	−0.1660	1.2074	0.027*
H9A	0.6240	−0.1401	1.2028	0.027*
N1B	0.7728 (3)	0.28829 (16)	0.93022 (15)	0.0236 (4)
H1B	0.765 (4)	0.227 (2)	0.965 (2)	0.027 (7)*
C2B	0.7435 (3)	0.31567 (17)	0.82677 (18)	0.0224 (5)
N3B	0.7231 (3)	0.42843 (15)	0.79407 (16)	0.0263 (5)
H3B	0.750 (4)	0.456 (2)	0.735 (2)	0.020 (6)*
C4B	0.7636 (4)	0.48437 (18)	0.88018 (18)	0.0280 (5)
H4BA	0.6611	0.5497	0.8833	0.034*
H4BB	0.8950	0.5105	0.8738	0.034*
C5B	0.7578 (4)	0.38891 (18)	0.97749 (18)	0.0266 (5)
H5BA	0.8704	0.3851	1.0267	0.032*
H5BB	0.6325	0.3996	1.0152	0.032*
N6B	0.7384 (3)	0.24212 (17)	0.76439 (17)	0.0275 (5)
H6BB	0.742 (4)	0.177 (2)	0.794 (2)	0.032 (7)*
H6BA	0.717 (4)	0.2707 (19)	0.700 (2)	0.020 (6)*
O1C	0.6385 (3)	0.33821 (18)	0.55175 (14)	0.0496 (5)
N1C	0.6926 (3)	0.29562 (18)	0.38911 (15)	0.0336 (5)
C1C	0.6495 (4)	0.3658 (2)	0.4563 (2)	0.0388 (6)
H1CA	0.6252	0.4445	0.4274	0.047*
C2C	0.7292 (5)	0.1734 (2)	0.4252 (2)	0.0477 (7)
H2CA	0.7208	0.1559	0.5019	0.072*
H2CB	0.8614	0.1441	0.4045	0.072*
H2CC	0.6301	0.1379	0.3934	0.072*
C3C	0.7023 (5)	0.3360 (3)	0.2762 (2)	0.0536 (8)
H3CA	0.6770	0.4190	0.2610	0.080*
H3CB	0.6024	0.3056	0.2397	0.080*
H3CC	0.8340	0.3106	0.2521	0.080*
O1D	0.8400 (3)	0.58284 (15)	0.62367 (14)	0.0491 (5)
N1D	0.8126 (3)	0.72687 (15)	0.48209 (14)	0.0252 (4)
C1D	0.8103 (4)	0.6845 (2)	0.58456 (18)	0.0330 (6)
H1D	0.7839	0.7366	0.6310	0.040*
C2D	0.8469 (4)	0.65334 (19)	0.40540 (19)	0.0325 (6)
H2DA	0.8733	0.5742	0.4419	0.049*
H2DB	0.9610	0.6726	0.3632	0.049*
H2DC	0.7296	0.6635	0.3593	0.049*
C3D	0.7716 (5)	0.84823 (19)	0.44212 (18)	0.0374 (7)
H3DA	0.7507	0.8883	0.5012	0.056*
H3DB	0.6526	0.8647	0.3967	0.056*
H3DC	0.8839	0.8734	0.4016	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0346 (4)	0.0317 (3)	0.0166 (3)	−0.0039 (3)	0.0002 (3)	−0.0062 (2)
S2A	0.0287 (3)	0.0186 (3)	0.0310 (3)	−0.0042 (2)	0.0013 (2)	0.0009 (2)
N1A	0.0238 (11)	0.0208 (8)	0.0162 (8)	−0.0017 (8)	−0.0001 (8)	−0.0026 (7)
C2A	0.0159 (12)	0.0216 (10)	0.0201 (10)	−0.0011 (9)	−0.0014 (9)	−0.0030 (8)
S3A	0.0347 (4)	0.0194 (3)	0.0233 (3)	−0.0025 (2)	−0.0010 (2)	−0.0058 (2)
C4A	0.0134 (12)	0.0206 (10)	0.0248 (11)	−0.0019 (8)	−0.0021 (9)	−0.0021 (8)
N5A	0.0210 (10)	0.0190 (8)	0.0159 (8)	0.0007 (7)	−0.0003 (7)	−0.0016 (6)
C6A	0.0191 (11)	0.0187 (10)	0.0170 (9)	0.0005 (8)	0.0001 (9)	0.0000 (8)
N7A	0.0285 (11)	0.0222 (9)	0.0168 (8)	−0.0033 (8)	−0.0006 (8)	−0.0043 (7)
C8A	0.0243 (13)	0.0270 (11)	0.0163 (10)	−0.0043 (10)	0.0006 (9)	−0.0059 (8)
C9A	0.0233 (13)	0.0248 (11)	0.0179 (10)	−0.0011 (9)	−0.0005 (9)	−0.0022 (8)
N1B	0.0294 (12)	0.0172 (9)	0.0232 (9)	−0.0038 (8)	0.0002 (8)	−0.0006 (8)
C2B	0.0174 (12)	0.0193 (10)	0.0290 (11)	−0.0008 (9)	0.0029 (9)	−0.0022 (9)
N3B	0.0334 (13)	0.0183 (9)	0.0262 (10)	−0.0053 (8)	0.0057 (9)	−0.0003 (8)
C4B	0.0313 (14)	0.0182 (10)	0.0343 (13)	−0.0034 (9)	0.0017 (11)	−0.0046 (9)
C5B	0.0284 (14)	0.0236 (11)	0.0286 (12)	−0.0027 (10)	0.0007 (10)	−0.0075 (9)
N6B	0.0377 (13)	0.0207 (10)	0.0237 (10)	−0.0047 (9)	0.0026 (9)	−0.0030 (8)
O1C	0.0513 (14)	0.0707 (14)	0.0281 (10)	−0.0133 (11)	−0.0030 (9)	−0.0089 (9)
N1C	0.0322 (13)	0.0425 (12)	0.0232 (10)	−0.0066 (10)	−0.0023 (9)	0.0024 (9)
C1C	0.0346 (17)	0.0461 (15)	0.0365 (14)	−0.0132 (13)	−0.0034 (13)	−0.0041 (12)
C2C	0.047 (2)	0.0425 (15)	0.0499 (17)	−0.0003 (14)	0.0001 (15)	−0.0027 (13)
C3C	0.053 (2)	0.074 (2)	0.0271 (13)	−0.0011 (17)	−0.0008 (14)	0.0007 (13)
O1D	0.0645 (15)	0.0369 (10)	0.0366 (10)	−0.0008 (10)	0.0105 (10)	0.0126 (8)
N1D	0.0314 (12)	0.0224 (9)	0.0207 (9)	−0.0032 (8)	0.0014 (9)	−0.0016 (7)
C1D	0.0376 (16)	0.0335 (12)	0.0251 (12)	−0.0045 (11)	0.0047 (11)	0.0013 (10)
C2D	0.0391 (16)	0.0282 (12)	0.0300 (12)	−0.0010 (11)	0.0039 (12)	−0.0073 (10)
C3D	0.063 (2)	0.0230 (11)	0.0244 (12)	−0.0014 (12)	−0.0032 (13)	−0.0034 (9)

Geometric parameters (Å, º)

S1A—C2A	1.687 (2)	C5B—H5BA	0.9900
S2A—C4A	1.657 (2)	C5B—H5BB	0.9900
N1A—C2A	1.307 (3)	N6B—H6BB	0.81 (3)
N1A—C6A	1.373 (3)	N6B—H6BA	0.85 (2)
C2A—S3A	1.782 (2)	O1C—C1C	1.224 (3)
S3A—C4A	1.756 (2)	N1C—C1C	1.333 (3)
C4A—N5A	1.340 (3)	N1C—C2C	1.456 (3)
N5A—C6A	1.424 (3)	N1C—C3C	1.457 (3)
N5A—C9A	1.472 (3)	C1C—H1CA	0.9500
C6A—N7A	1.282 (3)	C2C—H2CA	0.9800
N7A—C8A	1.471 (2)	C2C—H2CB	0.9800
C8A—C9A	1.542 (3)	C2C—H2CC	0.9800
C8A—H8B	0.9900	C3C—H3CA	0.9800
C8A—H8A	0.9900	C3C—H3CB	0.9800
C9A—H9B	0.9900	C3C—H3CC	0.9800
C9A—H9A	0.9900	O1D—C1D	1.232 (3)
N1B—C2B	1.327 (3)	N1D—C1D	1.331 (3)
N1B—C5B	1.456 (3)	N1D—C2D	1.452 (3)
N1B—H1B	0.81 (3)	N1D—C3D	1.455 (3)
C2B—N6B	1.315 (3)	C1D—H1D	0.9500
C2B—N3B	1.342 (3)	C2D—H2DA	0.9800
N3B—C4B	1.455 (3)	C2D—H2DB	0.9800
N3B—H3B	0.81 (3)	C2D—H2DC	0.9800
C4B—C5B	1.548 (3)	C3D—H3DA	0.9800
C4B—H4BA	0.9900	C3D—H3DB	0.9800
C4B—H4BB	0.9900	C3D—H3DC	0.9800
C2A—N1A—C6A	123.01 (17)	C4B—C5B—H5BA	111.3
N1A—C2A—S1A	123.67 (16)	N1B—C5B—H5BB	111.3
N1A—C2A—S3A	123.39 (15)	C4B—C5B—H5BB	111.3
S1A—C2A—S3A	112.95 (12)	H5BA—C5B—H5BB	109.2
C4A—S3A—C2A	104.71 (10)	C2B—N6B—H6BB	115.3 (19)
N5A—C4A—S2A	124.40 (16)	C2B—N6B—H6BA	115.2 (16)
N5A—C4A—S3A	117.30 (15)	H6BB—N6B—H6BA	129 (2)
S2A—C4A—S3A	118.30 (12)	C1C—N1C—C2C	121.3 (2)
C4A—N5A—C6A	128.01 (17)	C1C—N1C—C3C	122.3 (2)
C4A—N5A—C9A	123.64 (17)	C2C—N1C—C3C	116.4 (2)
C6A—N5A—C9A	108.35 (16)	O1C—C1C—N1C	126.0 (3)
N7A—C6A—N1A	122.48 (18)	O1C—C1C—H1CA	117.0
N7A—C6A—N5A	114.00 (18)	N1C—C1C—H1CA	117.0
N1A—C6A—N5A	123.52 (18)	N1C—C2C—H2CA	109.5
C6A—N7A—C8A	108.93 (17)	N1C—C2C—H2CB	109.5
N7A—C8A—C9A	106.84 (16)	H2CA—C2C—H2CB	109.5
N7A—C8A—H8B	110.4	N1C—C2C—H2CC	109.5
C9A—C8A—H8B	110.4	H2CA—C2C—H2CC	109.5
N7A—C8A—H8A	110.4	H2CB—C2C—H2CC	109.5
C9A—C8A—H8A	110.4	N1C—C3C—H3CA	109.5
H8B—C8A—H8A	108.6	N1C—C3C—H3CB	109.5
N5A—C9A—C8A	101.81 (15)	H3CA—C3C—H3CB	109.5
N5A—C9A—H9B	111.4	N1C—C3C—H3CC	109.5
C8A—C9A—H9B	111.4	H3CA—C3C—H3CC	109.5
N5A—C9A—H9A	111.4	H3CB—C3C—H3CC	109.5
C8A—C9A—H9A	111.4	C1D—N1D—C2D	121.24 (19)
H9B—C9A—H9A	109.3	C1D—N1D—C3D	121.4 (2)
C2B—N1B—C5B	111.22 (18)	C2D—N1D—C3D	117.33 (18)
C2B—N1B—H1B	124.7 (18)	O1D—C1D—N1D	124.8 (2)
C5B—N1B—H1B	121.5 (18)	O1D—C1D—H1D	117.6
N6B—C2B—N1B	124.5 (2)	N1D—C1D—H1D	117.6
N6B—C2B—N3B	124.5 (2)	N1D—C2D—H2DA	109.5
N1B—C2B—N3B	111.0 (2)	N1D—C2D—H2DB	109.5
C2B—N3B—C4B	110.62 (19)	H2DA—C2D—H2DB	109.5
C2B—N3B—H3B	120.9 (17)	N1D—C2D—H2DC	109.5
C4B—N3B—H3B	119.5 (18)	H2DA—C2D—H2DC	109.5
N3B—C4B—C5B	102.30 (17)	H2DB—C2D—H2DC	109.5
N3B—C4B—H4BA	111.3	N1D—C3D—H3DA	109.5
C5B—C4B—H4BA	111.3	N1D—C3D—H3DB	109.5
N3B—C4B—H4BB	111.3	H3DA—C3D—H3DB	109.5
C5B—C4B—H4BB	111.3	N1D—C3D—H3DC	109.5
H4BA—C4B—H4BB	109.2	H3DA—C3D—H3DC	109.5
N1B—C5B—C4B	102.14 (18)	H3DB—C3D—H3DC	109.5
N1B—C5B—H5BA	111.3
C6A—N1A—C2A—S1A	−179.33 (17)	N5A—C6A—N7A—C8A	1.1 (3)
C6A—N1A—C2A—S3A	0.8 (3)	C6A—N7A—C8A—C9A	−2.4 (3)
N1A—C2A—S3A—C4A	1.3 (2)	C4A—N5A—C9A—C8A	178.2 (2)
S1A—C2A—S3A—C4A	−178.67 (13)	C6A—N5A—C9A—C8A	−2.1 (2)
C2A—S3A—C4A—N5A	−2.1 (2)	N7A—C8A—C9A—N5A	2.6 (2)
C2A—S3A—C4A—S2A	177.92 (14)	C5B—N1B—C2B—N6B	−176.4 (2)
S2A—C4A—N5A—C6A	−178.78 (18)	C5B—N1B—C2B—N3B	4.6 (3)
S3A—C4A—N5A—C6A	1.2 (3)	N6B—C2B—N3B—C4B	−172.0 (2)
S2A—C4A—N5A—C9A	0.9 (3)	N1B—C2B—N3B—C4B	7.0 (3)
S3A—C4A—N5A—C9A	−179.10 (17)	C2B—N3B—C4B—C5B	−14.5 (3)
C2A—N1A—C6A—N7A	178.6 (2)	C2B—N1B—C5B—C4B	−13.1 (3)
C2A—N1A—C6A—N5A	−2.2 (4)	N3B—C4B—C5B—N1B	15.8 (2)
C4A—N5A—C6A—N7A	−179.6 (2)	C2C—N1C—C1C—O1C	1.0 (5)
C9A—N5A—C6A—N7A	0.7 (3)	C3C—N1C—C1C—O1C	179.9 (3)
C4A—N5A—C6A—N1A	1.1 (4)	C2D—N1D—C1D—O1D	1.5 (4)
C9A—N5A—C6A—N1A	−178.6 (2)	C3D—N1D—C1D—O1D	178.6 (3)
N1A—C6A—N7A—C8A	−179.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···N7A	0.81 (3)	2.11 (3)	2.916 (3)	178 (3)
N3B—H3B···O1D	0.81 (3)	2.07 (3)	2.806 (3)	153 (2)
N6B—H6BB···N1A	0.81 (3)	2.14 (3)	2.952 (3)	173 (3)
N6B—H6BA···O1C	0.85 (2)	1.98 (3)	2.827 (3)	174 (3)