4-Bromo-2-{[4-(3-mesityl-3-methyl­cyclo­butyl)thia­zol-2-yl]hydrazono­meth­yl}phenol, with N—H...N, C—H...π and π–π inter­actions

The title compound, C₂₄H₂₆BrN₃OS, crystallizes in the triclinic space group P, with two independent mol­ecules in the asymmetric unit. The mol­ecules adopt an E geometry about the azomethine C=N double bond. The structure is stabilized as dimers by N—H...N hydrogen bonding. C—H...π and π–π inter­actions are also effective in the crystal packing.

S1. Comment

Hydrazine is a highly reactive base and reducing agent. Its primary uses are as a high-energy rocket propellant, as a reactant in military fuel cells, in nickel plating, in the polymerization of urethane, for removal of halogens from wastewater, as an oxygen scavenger in boiler feed water to inhibit corrosion and in photographic development (Von Burg & Stout, 1991). Hydrazine was historically used experimentally as a therapeutic agent in the treatment of tuberculosis, sickle cell anemia and non-specific chronic illnesses (Von Burg & Stout, 1991; Gold, 1987). Moreover, hydrazones are frequently more efficient than oximes in this reaction since the greater molecular weight of hydrazones causes a lower solubility in most solvents and they can, therefore, often be more easily isolated and recrystallized. Hydrazones have been widely studied as chelating ligands for the spectrophotometric and flouorimetric determination of trace metal ions (Katyal & Dutt, 1975; Galiano-Roth & Collum, 1988).

The title compound, (I), crystallizes in the triclinic space group P1, with two independent molecules in the asymmetric unit. A view of the asymmetric unit with the atom-labeling scheme is shown in Fig. 1. The structure of (I) was initially identified by NMR and IR spectroscopy. The crystal structure determination of (I) was carried out in order to compare the double-bond geometry of this compound with those found in related compounds containing the thiazole moiety, such as 2-({4-[3-methyl-3-(2,4,6-trimethylphenyl)cyclobutyl]-3H-thiazol-2-ylidene}hydrazonomethyl)benzene-1,4-diol ethanol solvate (Yüksektepe et al., 2005), (II), and to obtain more detailed information on the structural conformation of the molecule, which may be of value in structure–activity analysis.

The molecules of (I) adopt an E geometry about the azomethine C═N double bond, with an N2—N3═C18—C19 torsion angle of 175.5 (3)° in molecule A and 177.7 (2)° in molecule B (Fig. 1). The skeleton of the molecules (except for the mesityl and methylcyclobutane moieties) deviates significantly from planarity. The r.m.s. deviations from the planes passing through all non-H atoms for the 3-bromo, 5-hydroxybenzene, thiazole and hydrazine moieties are 0.1492 (for molecule A) and 0.1072 Å (for molecule B). The dihedral angles between the 3-bromo-5-hydroxybenzene plane A (C19—C24), the thiazole plane B (N1/C15/C16/S1/C17) and the mesityl plane C (C5—C10) are 17.47(0.11) and 13.21(0.09)° (A/B), 13.00 (15) and 5.36 (18)° (A/C), and 4.75 (14) and 8.09 (15)° (B/C), respectively, for molecules A and B. In the thiazole ring, the S1—C16 and S1—C17 bond lengths (Table 1) are shorter than the accepted value for an S—Csp² single bond (1.76 Å; Allen, 1984).

In the cyclobutane ring, the C4/C1/C2 plane forms a dihedral angle of 26.57 (3)° in molecule A and 29.55 (2)° in molecule B with the C2/C3/C4 plane. Literature values for the puckering of the cyclobutane ring are 23.5 (Swenson et al., 1997), 29.03 (13) (Yüksektepe et al., 2004) and 26.8 (2)° for (II). These values are comparable to the reported values for (I).

An interesting feature was found in the crystal packing. While electron delocalization occurs along the hydrazine moiety in molecule A and (II), the H atom is transferred to atom N2B of the hydrazine group from atom N1B of the thiazole moiety in molecule B. In consequence of this H-atom migration, the independent molecules in the asymmetric unit are linked by strong N—H···N hydrogen bonds into a dimer in the R₂²(8) formation (Bernstein et al., 1995) (Figs. 2 and 3, and Table 2). Similar dimeric assembly has not been reported before for related structures. The C17A—N1A and C15A—N1A bonds [1.339 (4) and 1.394 (4) Å, respectively] are longer than the corresponding bonds of molecule B [1.318 (4) Å and 1.387 (4) Å]. The N2B—C17B bond [1.348 (4) Å] is also longer than the N2A—C17A bond [1.327 (4) Å]. Intramolecular O—H···N hydrogen bonds are also effective in the crystal packing (Table 2, and Figs. 2 and 3).

Of greater interest are the intermolecular π-ring interactions with the mesityl plane and methyl group (C12A—H12C···Cg1; Cg1 is C5A—C10A), which stabilize the molecules in the crystal. This C—H···π interaction links the above-mentioned dimers again as a dimeric form, thus forming tetramers (Fig. 2 and Table 2). Additionally, π–π interactions between the 3-bromo-5-hydroxybenzene rings of molecule B (Cg2, C19B—C24B) is also effective in the molecular packing in the crystal structure (the distance between centroids is 3.814 (2) Å and the perpendicular distance is 3.41 Å; Fig. 3). Propagation of C—H···π and π—π interactions by inversion thus links the R₂²(8) dimers into a chain of these rings parallel to the [011] direction.

S2. Experimental

To an alcoholic suspension of 1-(2-hydroxy-5-bromobenzylidene)thiosemicarbazide (1.3707 g, 5 mmol), a solution of 1-methyl-1-mesityl-3-(2-chloro-1-oxoethyl)cyclobutane (1.3225 g, 5 mmol) in absolute ethanol (20 ml) was added dropwise at ca 323–328 K with continuous stirring. After the addition of the α-haloketone, the temperature was kept at 323–328 K for a further 2 h. After cooling to room temperature, the solution was then made alkaline with an aqueous solution of NH₃ (5%), and a light-yellow precipitate separated. The precipitate was filtered off, washed with aqueous NH₃ solution several times and dried in air. Suitable single crystals for crystal structure determination were obtained by slow evaporation of an ethanol solution. Yield 87%, m.p. 503 K. IR (cm⁻¹): 3285 ν(O—H), 1165 ν(C—O), 1625 ν(C═N thiazole), 1600 ν(C═N azomethine), 3131 ν(N—H), 655 ν(C—S—C thiazole). Characteristic ¹H NMR shifts (CDCl₃, p.p.m.): δ 1.49 (s, 3H, –CH₃ on cyclobutane), 2.14 (s, 6H, o-CH₃), 2.39 (s, 3H, p-CH₃), 2.54 (m, 4H, –CH₂– cyclobutane), 3.31 (q, 1H, >CH– cyclobutane), 5.96 (s, 1H, thiazole), 6.7–7.4 (m, 5H, aromatics), 8.02 (s, 1H, azomethine).

S3. Refinement

The H atoms on atoms N1A and N2B were located at the end of the refinement in a Fourier difference synthesis. Once located, they were refined as riding (N—H = 0.86 Å). All other H atoms were placed in calculated positions and refined as riding, with C—H distances in the range 0.93–0.98 Å and O—H distances of 0.82 Å. The U_iso(H) values were set at 1.2 or 1.5 times U_eq of the parent atom.

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. : Views of the dimers formed in the crystal structure of (I). Displacement ellipsoids are drawn at the 50% probability level and the atom-numbering scheme is given. Hydrogen bonds are shown as dashed lines.
	Fig. 2. : A partial packing diagram for (I), showing the N—H···N and C—H···π interactions as dotted lines. Cg1 is the centroid of the C5A—C10A ring. [Symmetry code: (i) −x, −y + 2, − z + 1.]
	Fig. 3. : A partial packing diagram for (I), showing the N—H···N and π–π interactions. Cg2 is the centroid of the C19B–C24B ring. [Symmetry code: (ii) −x, −y + 1, −z.]

4-Bromo-2-{[4-(3-mesityl-3-methylcyclobutyl)thiazol-2- yl]hydrazonomethyl}phenol

Crystal data

C24H26BrN3OS	Z = 4
Mr = 484.45	F(000) = 1000
Triclinic, P1	Dx = 1.407 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3589 (5) Å	Cell parameters from 24578 reflections
b = 11.9903 (7) Å	θ = 1.7–27.2°
c = 24.1438 (14) Å	µ = 1.91 mm^−1
α = 75.507 (5)°	T = 293 K
β = 86.063 (5)°	Plate, colorless
γ = 77.418 (5)°	0.40 × 0.31 × 0.07 mm
V = 2286.3 (2) Å^3

Data collection

STOE IPDS-II diffractometer	8041 independent reflections
Radiation source: fine-focus sealed tube	5444 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
Detector resolution: 6.67 pixels mm^-1	θmax = 25.0°, θmin = 1.7°
rotation method scans	h = −9→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
Tmin = 0.396, Tmax = 0.877	l = −28→28
27215 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0449P)^2] where P = (Fo^2 + 2Fc^2)/3
8041 reflections	(Δ/σ)max = 0.005
547 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.50 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
Br1A	0.18264 (7)	0.87358 (5)	−0.244543 (19)	0.09687 (18)
S1A	0.26983 (13)	1.10008 (7)	0.07543 (4)	0.0667 (3)
N1A	0.4044 (3)	0.9132 (2)	0.14726 (10)	0.0492 (6)
H1N	0.4501	0.8414	0.1624	0.059*
N2A	0.3665 (3)	0.8826 (2)	0.05665 (11)	0.0548 (7)
N3A	0.2878 (3)	0.9457 (2)	0.00618 (11)	0.0533 (7)
O1A	0.0793 (3)	1.1224 (2)	−0.05388 (11)	0.0760 (7)
H1O	0.1364	1.0856	−0.0262	0.114*
C1A	0.4246 (4)	0.9823 (3)	0.23728 (14)	0.0530 (8)
H1A	0.5441	0.9697	0.2395	0.064*
C2A	0.3418 (5)	1.0807 (3)	0.26662 (15)	0.0608 (9)
H2A	0.2349	1.1224	0.2515	0.073*
H2B	0.4108	1.1355	0.2679	0.073*
C3A	0.3340 (4)	0.9873 (3)	0.32415 (14)	0.0551 (8)
C4A	0.3590 (4)	0.8950 (3)	0.28656 (13)	0.0514 (8)
H4A	0.4394	0.8238	0.3016	0.062*
H4B	0.2576	0.8764	0.2779	0.062*
C5A	0.1794 (4)	0.9974 (3)	0.36140 (14)	0.0545 (8)
C6A	0.0830 (5)	1.1076 (3)	0.36546 (15)	0.0655 (10)
C7A	−0.0552 (5)	1.1114 (4)	0.40085 (17)	0.0753 (12)
H7A	−0.1180	1.1848	0.4025	0.090*
C8A	−0.1042 (5)	1.0135 (4)	0.43341 (18)	0.0766 (11)
C9A	−0.0076 (5)	0.9065 (4)	0.43008 (17)	0.0746 (11)
H9A	−0.0376	0.8381	0.4517	0.090*
C10A	0.1331 (4)	0.8963 (3)	0.39575 (15)	0.0604 (9)
C11A	0.1254 (6)	1.2233 (3)	0.3352 (2)	0.0958 (15)
H11A	0.2408	1.2183	0.3383	0.144*
H11B	0.0650	1.2842	0.3523	0.144*
H11C	0.0976	1.2414	0.2955	0.144*
C12A	−0.2541 (5)	1.0213 (5)	0.4727 (2)	0.1058 (17)
H12A	−0.2912	0.9485	0.4809	0.159*
H12B	−0.3397	1.0844	0.4543	0.159*
H12C	−0.2260	1.0361	0.5077	0.159*
C13A	0.2333 (5)	0.7727 (3)	0.40088 (18)	0.0799 (11)
H13A	0.3469	0.7723	0.4048	0.120*
H13B	0.2196	0.7471	0.3672	0.120*
H13C	0.1967	0.7204	0.4339	0.120*
C14A	0.4836 (5)	0.9733 (4)	0.36032 (17)	0.0750 (11)
H14A	0.5810	0.9665	0.3368	0.112*
H14B	0.4911	0.9038	0.3910	0.112*
H14C	0.4727	1.0410	0.3759	0.112*
C15A	0.3758 (4)	1.0021 (3)	0.17669 (13)	0.0521 (8)
C16A	0.3060 (5)	1.1057 (3)	0.14373 (15)	0.0657 (10)
H16A	0.2793	1.1746	0.1565	0.079*
C17A	0.3536 (4)	0.9508 (3)	0.09307 (13)	0.0490 (7)
C18A	0.3050 (4)	0.8960 (3)	−0.03566 (13)	0.0508 (8)
H18A	0.3746	0.8227	−0.0322	0.061*
C19A	0.2172 (4)	0.9528 (3)	−0.08823 (13)	0.0504 (8)
C20A	0.2391 (4)	0.8971 (3)	−0.13336 (14)	0.0578 (8)
H20A	0.3124	0.8253	−0.1298	0.069*
C21A	0.1530 (5)	0.9478 (3)	−0.18302 (15)	0.0646 (9)
C22A	0.0445 (5)	1.0547 (4)	−0.18910 (17)	0.0734 (11)
H22A	−0.0129	1.0885	−0.2229	0.088*
C23A	0.0210 (5)	1.1112 (3)	−0.14532 (17)	0.0715 (10)
H23A	−0.0531	1.1828	−0.1496	0.086*
C24A	0.1064 (4)	1.0627 (3)	−0.09492 (15)	0.0578 (8)
Br1B	−0.06327 (4)	0.60101 (3)	−0.160046 (15)	0.06310 (12)
S1B	0.52158 (11)	0.43925 (7)	0.16823 (4)	0.0566 (2)
N1B	0.5030 (3)	0.6514 (2)	0.17666 (10)	0.0461 (6)
N2B	0.3460 (3)	0.6400 (2)	0.10245 (11)	0.0526 (7)
H2N	0.2956	0.7125	0.0961	0.063*
N3B	0.3257 (3)	0.5672 (2)	0.06846 (10)	0.0462 (6)
O1B	0.3892 (3)	0.36565 (18)	0.03793 (9)	0.0596 (6)
H2O	0.3964	0.4110	0.0576	0.089*
C1B	0.6824 (4)	0.6336 (3)	0.25678 (13)	0.0514 (8)
H1B	0.6297	0.7171	0.2501	0.062*
C2B	0.8691 (4)	0.6208 (3)	0.25665 (14)	0.0543 (8)
H2C	0.9068	0.6889	0.2333	0.065*
H2D	0.9295	0.5490	0.2472	0.065*
C3B	0.8627 (4)	0.6153 (3)	0.32189 (13)	0.0478 (7)
C4B	0.6946 (4)	0.5789 (3)	0.32153 (14)	0.0558 (8)
H4C	0.7021	0.4944	0.3318	0.067*
H4D	0.6095	0.6176	0.3438	0.067*
C5B	0.9986 (4)	0.5331 (3)	0.35963 (14)	0.0482 (7)
C6B	1.1639 (4)	0.5231 (3)	0.34104 (16)	0.0590 (9)
C7B	1.2858 (5)	0.4477 (4)	0.3771 (2)	0.0792 (12)
H7B	1.3942	0.4407	0.3644	0.095*
C8B	1.2536 (6)	0.3836 (4)	0.4304 (2)	0.0883 (14)
C9B	1.0941 (6)	0.3977 (4)	0.44876 (18)	0.0807 (12)
H9B	1.0704	0.3568	0.4855	0.097*
C10B	0.9658 (4)	0.4698 (3)	0.41534 (15)	0.0589 (9)
C11B	1.2163 (5)	0.5922 (4)	0.28422 (19)	0.0834 (12)
H11D	1.1511	0.6707	0.2761	0.125*
H11E	1.2016	0.5546	0.2547	0.125*
H11F	1.3298	0.5952	0.2856	0.125*
C12B	1.3931 (7)	0.3019 (5)	0.4676 (3)	0.151 (3)
H12D	1.3484	0.2537	0.5003	0.227*
H12E	1.4574	0.3481	0.4801	0.227*
H12F	1.4613	0.2525	0.4458	0.227*
C13B	0.7969 (5)	0.4781 (5)	0.44131 (16)	0.0882 (13)
H13D	0.7376	0.5582	0.4310	0.106*
H13E	0.8043	0.4521	0.4822	0.106*
H13F	0.7405	0.4291	0.4274	0.106*
C14B	0.8379 (5)	0.7386 (3)	0.33286 (17)	0.0703 (10)
H14D	0.7520	0.7911	0.3090	0.105*
H14E	0.9378	0.7670	0.3242	0.105*
H14F	0.8083	0.7348	0.3723	0.105*
C15B	0.6076 (4)	0.5783 (3)	0.21914 (13)	0.0463 (7)
C16B	0.6310 (4)	0.4636 (3)	0.22079 (15)	0.0573 (8)
H16B	0.6977	0.4044	0.2469	0.069*
C17B	0.4501 (3)	0.5899 (2)	0.14625 (12)	0.0437 (7)
C18B	0.2298 (4)	0.6116 (3)	0.02600 (13)	0.0444 (7)
H18B	0.1740	0.6896	0.0200	0.053*
C19B	0.2064 (3)	0.5419 (2)	−0.01318 (12)	0.0421 (7)
C20B	0.1035 (3)	0.5939 (3)	−0.05961 (12)	0.0449 (7)
H20B	0.0517	0.6728	−0.0656	0.054*
C21B	0.0778 (4)	0.5296 (3)	−0.09687 (12)	0.0453 (7)
C22B	0.1545 (4)	0.4123 (3)	−0.08898 (13)	0.0499 (7)
H22B	0.1359	0.3693	−0.1141	0.060*
C23B	0.2580 (4)	0.3599 (3)	−0.04384 (13)	0.0511 (8)
H23B	0.3103	0.2813	−0.0387	0.061*
C24B	0.2854 (4)	0.4228 (2)	−0.00591 (12)	0.0443 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.1332 (4)	0.1162 (4)	0.0585 (3)	−0.0529 (3)	−0.0112 (3)	−0.0267 (2)
S1A	0.0992 (7)	0.0399 (4)	0.0528 (5)	−0.0007 (4)	−0.0037 (5)	−0.0073 (4)
N1A	0.0608 (16)	0.0400 (14)	0.0449 (15)	−0.0053 (12)	−0.0038 (12)	−0.0105 (11)
N2A	0.0714 (18)	0.0458 (15)	0.0444 (15)	−0.0049 (13)	−0.0086 (13)	−0.0101 (12)
N3A	0.0679 (17)	0.0443 (14)	0.0440 (15)	−0.0082 (13)	−0.0037 (13)	−0.0060 (12)
O1A	0.0918 (18)	0.0547 (14)	0.0729 (17)	0.0056 (13)	−0.0147 (14)	−0.0142 (13)
C1A	0.0550 (19)	0.0546 (19)	0.0532 (19)	−0.0112 (15)	−0.0041 (15)	−0.0192 (16)
C2A	0.079 (2)	0.0499 (19)	0.062 (2)	−0.0168 (17)	0.0006 (18)	−0.0263 (17)
C3A	0.065 (2)	0.0500 (18)	0.0553 (19)	−0.0061 (15)	−0.0076 (16)	−0.0245 (16)
C4A	0.0613 (19)	0.0463 (17)	0.0495 (18)	−0.0042 (15)	−0.0079 (15)	−0.0208 (15)
C5A	0.063 (2)	0.060 (2)	0.0453 (18)	−0.0030 (16)	−0.0108 (15)	−0.0270 (16)
C6A	0.083 (3)	0.061 (2)	0.057 (2)	−0.0021 (18)	−0.0130 (19)	−0.0312 (18)
C7A	0.075 (3)	0.088 (3)	0.063 (2)	0.015 (2)	−0.010 (2)	−0.042 (2)
C8A	0.067 (2)	0.105 (3)	0.063 (2)	−0.008 (2)	−0.007 (2)	−0.038 (2)
C9A	0.082 (3)	0.089 (3)	0.058 (2)	−0.022 (2)	−0.004 (2)	−0.024 (2)
C10A	0.070 (2)	0.064 (2)	0.0495 (19)	−0.0095 (17)	−0.0083 (17)	−0.0201 (17)
C11A	0.143 (4)	0.060 (3)	0.088 (3)	−0.004 (3)	0.001 (3)	−0.040 (2)
C12A	0.067 (3)	0.165 (5)	0.095 (3)	−0.011 (3)	0.005 (2)	−0.063 (3)
C13A	0.100 (3)	0.065 (2)	0.070 (3)	−0.014 (2)	0.005 (2)	−0.013 (2)
C14A	0.074 (2)	0.093 (3)	0.070 (2)	−0.016 (2)	−0.013 (2)	−0.039 (2)
C15A	0.065 (2)	0.0438 (17)	0.0492 (18)	−0.0089 (15)	0.0010 (15)	−0.0169 (14)
C16A	0.096 (3)	0.0431 (18)	0.058 (2)	−0.0047 (18)	−0.0008 (19)	−0.0193 (16)
C17A	0.0575 (19)	0.0380 (16)	0.0479 (18)	−0.0057 (14)	0.0040 (15)	−0.0088 (14)
C18A	0.0565 (19)	0.0455 (17)	0.0480 (18)	−0.0093 (14)	0.0002 (15)	−0.0085 (14)
C19A	0.0539 (19)	0.0492 (18)	0.0459 (18)	−0.0124 (15)	−0.0053 (15)	−0.0048 (14)
C20A	0.065 (2)	0.059 (2)	0.0490 (19)	−0.0189 (17)	0.0003 (16)	−0.0081 (16)
C21A	0.070 (2)	0.077 (2)	0.050 (2)	−0.032 (2)	−0.0070 (17)	−0.0058 (18)
C22A	0.077 (3)	0.080 (3)	0.060 (2)	−0.028 (2)	−0.021 (2)	0.005 (2)
C23A	0.071 (2)	0.065 (2)	0.068 (2)	−0.0134 (19)	−0.014 (2)	0.006 (2)
C24A	0.062 (2)	0.055 (2)	0.055 (2)	−0.0172 (16)	−0.0033 (17)	−0.0055 (16)
Br1B	0.0645 (2)	0.0692 (2)	0.0543 (2)	0.00107 (16)	−0.01158 (16)	−0.02258 (17)
S1B	0.0639 (5)	0.0439 (4)	0.0635 (5)	−0.0074 (4)	−0.0123 (4)	−0.0158 (4)
N1B	0.0544 (15)	0.0454 (14)	0.0392 (13)	−0.0089 (11)	−0.0031 (11)	−0.0125 (11)
N2B	0.0645 (17)	0.0440 (14)	0.0520 (16)	−0.0052 (12)	−0.0119 (13)	−0.0187 (12)
N3B	0.0539 (15)	0.0437 (13)	0.0451 (14)	−0.0142 (11)	−0.0011 (12)	−0.0145 (11)
O1B	0.0769 (15)	0.0427 (12)	0.0557 (13)	0.0001 (11)	−0.0144 (12)	−0.0130 (10)
C1B	0.0554 (18)	0.0490 (18)	0.0495 (18)	0.0004 (14)	−0.0070 (15)	−0.0193 (15)
C2B	0.063 (2)	0.0560 (19)	0.0484 (18)	−0.0217 (16)	0.0028 (15)	−0.0132 (15)
C3B	0.0481 (17)	0.0476 (17)	0.0504 (18)	−0.0082 (13)	−0.0010 (14)	−0.0186 (14)
C4B	0.0471 (18)	0.075 (2)	0.0491 (19)	−0.0106 (16)	−0.0017 (15)	−0.0230 (17)
C5B	0.0494 (18)	0.0470 (17)	0.0544 (19)	−0.0110 (14)	−0.0042 (14)	−0.0220 (15)
C6B	0.0492 (19)	0.057 (2)	0.079 (2)	−0.0116 (15)	0.0010 (17)	−0.0322 (18)
C7B	0.049 (2)	0.075 (3)	0.122 (4)	−0.0033 (19)	−0.014 (2)	−0.042 (3)
C8B	0.086 (3)	0.065 (3)	0.112 (4)	−0.004 (2)	−0.037 (3)	−0.019 (3)
C9B	0.095 (3)	0.076 (3)	0.069 (3)	−0.022 (2)	−0.027 (2)	−0.003 (2)
C10B	0.064 (2)	0.062 (2)	0.053 (2)	−0.0179 (17)	−0.0072 (17)	−0.0126 (17)
C11B	0.059 (2)	0.106 (3)	0.096 (3)	−0.035 (2)	0.017 (2)	−0.033 (3)
C12B	0.121 (5)	0.116 (4)	0.192 (7)	0.023 (4)	−0.087 (5)	−0.010 (4)
C13B	0.086 (3)	0.135 (4)	0.044 (2)	−0.039 (3)	0.000 (2)	−0.007 (2)
C14B	0.081 (2)	0.056 (2)	0.077 (3)	0.0021 (18)	−0.022 (2)	−0.0291 (18)
C15B	0.0463 (17)	0.0490 (18)	0.0434 (17)	−0.0076 (14)	−0.0024 (13)	−0.0124 (14)
C16B	0.0582 (19)	0.0514 (19)	0.059 (2)	0.0008 (15)	−0.0147 (16)	−0.0144 (16)
C17B	0.0462 (16)	0.0405 (16)	0.0434 (17)	−0.0076 (13)	0.0016 (14)	−0.0101 (13)
C18B	0.0470 (17)	0.0402 (16)	0.0458 (17)	−0.0098 (13)	−0.0005 (14)	−0.0094 (13)
C19B	0.0435 (16)	0.0390 (16)	0.0443 (16)	−0.0109 (13)	0.0045 (13)	−0.0101 (13)
C20B	0.0438 (16)	0.0441 (16)	0.0465 (17)	−0.0063 (13)	0.0021 (13)	−0.0137 (14)
C21B	0.0448 (16)	0.0501 (18)	0.0416 (16)	−0.0100 (13)	0.0019 (13)	−0.0127 (14)
C22B	0.0613 (19)	0.0490 (18)	0.0450 (17)	−0.0160 (15)	0.0045 (15)	−0.0188 (14)
C23B	0.063 (2)	0.0383 (16)	0.0506 (18)	−0.0095 (14)	0.0046 (16)	−0.0110 (14)
C24B	0.0470 (16)	0.0434 (16)	0.0415 (16)	−0.0086 (13)	0.0022 (13)	−0.0097 (13)

Geometric parameters (Å, º)

Br1A—C21A	1.891 (4)	Br1B—C21B	1.898 (3)
S1A—C16A	1.717 (4)	S1B—C16B	1.730 (3)
S1A—C17A	1.729 (3)	S1B—C17B	1.730 (3)
N1A—C17A	1.339 (4)	N1B—C17B	1.318 (4)
N1A—C15A	1.394 (4)	N1B—C15B	1.387 (4)
N1A—H1N	0.8600	N2B—C17B	1.348 (4)
N2A—C17A	1.327 (4)	N2B—N3B	1.381 (3)
N2A—N3A	1.386 (3)	N2B—H2N	0.8600
N3A—C18A	1.281 (4)	N3B—C18B	1.277 (4)
O1A—C24A	1.341 (4)	O1B—C24B	1.359 (3)
O1A—H1O	0.8200	O1B—H2O	0.8200
C1A—C15A	1.493 (4)	C1B—C15B	1.489 (4)
C1A—C4A	1.533 (5)	C1B—C2B	1.534 (4)
C1A—C2A	1.539 (4)	C1B—C4B	1.537 (4)
C1A—H1A	0.9800	C1B—H1B	0.9800
C2A—C3A	1.558 (5)	C2B—C3B	1.558 (4)
C2A—H2A	0.9700	C2B—H2C	0.9700
C2A—H2B	0.9700	C2B—H2D	0.9700
C3A—C5A	1.524 (5)	C3B—C5B	1.515 (4)
C3A—C14A	1.530 (5)	C3B—C14B	1.534 (4)
C3A—C4A	1.571 (4)	C3B—C4B	1.561 (4)
C4A—H4A	0.9700	C4B—H4C	0.9700
C4A—H4B	0.9700	C4B—H4D	0.9700
C5A—C10A	1.401 (5)	C5B—C10B	1.410 (5)
C5A—C6A	1.412 (4)	C5B—C6B	1.412 (5)
C6A—C7A	1.388 (6)	C6B—C7B	1.394 (5)
C6A—C11A	1.503 (6)	C6B—C11B	1.506 (5)
C7A—C8A	1.366 (6)	C7B—C8B	1.366 (6)
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.377 (6)	C8B—C9B	1.364 (6)
C8A—C12A	1.520 (6)	C8B—C12B	1.527 (6)
C9A—C10A	1.392 (5)	C9B—C10B	1.384 (5)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C13A	1.515 (5)	C10B—C13B	1.499 (5)
C11A—H11A	0.9600	C11B—H11D	0.9600
C11A—H11B	0.9600	C11B—H11E	0.9600
C11A—H11C	0.9600	C11B—H11F	0.9600
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600
C15A—C16A	1.331 (4)	C15B—C16B	1.337 (4)
C16A—H16A	0.9300	C16B—H16B	0.9300
C18A—C19A	1.446 (4)	C18B—C19B	1.458 (4)
C18A—H18A	0.9300	C18B—H18B	0.9300
C19A—C20A	1.396 (5)	C19B—C20B	1.390 (4)
C19A—C24A	1.415 (4)	C19B—C24B	1.409 (4)
C20A—C21A	1.374 (5)	C20B—C21B	1.377 (4)
C20A—H20A	0.9300	C20B—H20B	0.9300
C21A—C22A	1.379 (5)	C21B—C22B	1.384 (4)
C22A—C23A	1.374 (6)	C22B—C23B	1.372 (4)
C22A—H22A	0.9300	C22B—H22B	0.9300
C23A—C24A	1.383 (5)	C23B—C24B	1.382 (4)
C23A—H23A	0.9300	C23B—H23B	0.9300
C16A—S1A—C17A	89.19 (15)	C16B—S1B—C17B	88.49 (15)
C17A—N1A—C15A	113.3 (2)	C17B—N1B—C15B	110.9 (2)
C17A—N1A—H1N	123.4	C17B—N2B—N3B	115.5 (2)
C15A—N1A—H1N	123.4	C17B—N2B—H2N	122.2
C17A—N2A—N3A	110.1 (2)	N3B—N2B—H2N	122.2
C18A—N3A—N2A	117.5 (2)	C18B—N3B—N2B	117.6 (2)
C24A—O1A—H1O	109.5	C24B—O1B—H2O	109.5
C15A—C1A—C4A	122.4 (3)	C15B—C1B—C2B	119.9 (3)
C15A—C1A—C2A	114.5 (3)	C15B—C1B—C4B	120.4 (3)
C4A—C1A—C2A	87.9 (2)	C2B—C1B—C4B	86.7 (2)
C15A—C1A—H1A	110.0	C15B—C1B—H1B	109.3
C4A—C1A—H1A	110.0	C2B—C1B—H1B	109.3
C2A—C1A—H1A	110.0	C4B—C1B—H1B	109.3
C1A—C2A—C3A	90.0 (2)	C1B—C2B—C3B	90.2 (2)
C1A—C2A—H2A	113.6	C1B—C2B—H2C	113.6
C3A—C2A—H2A	113.6	C3B—C2B—H2C	113.6
C1A—C2A—H2B	113.6	C1B—C2B—H2D	113.6
C3A—C2A—H2B	113.6	C3B—C2B—H2D	113.6
H2A—C2A—H2B	110.9	H2C—C2B—H2D	110.9
C5A—C3A—C14A	109.6 (3)	C5B—C3B—C14B	109.1 (3)
C5A—C3A—C2A	119.6 (3)	C5B—C3B—C2B	119.2 (3)
C14A—C3A—C2A	110.3 (3)	C14B—C3B—C2B	111.4 (3)
C5A—C3A—C4A	117.0 (3)	C5B—C3B—C4B	119.5 (3)
C14A—C3A—C4A	112.6 (3)	C14B—C3B—C4B	110.7 (3)
C2A—C3A—C4A	85.9 (2)	C2B—C3B—C4B	85.1 (2)
C1A—C4A—C3A	89.8 (2)	C1B—C4B—C3B	90.0 (2)
C1A—C4A—H4A	113.7	C1B—C4B—H4C	113.6
C3A—C4A—H4A	113.7	C3B—C4B—H4C	113.6
C1A—C4A—H4B	113.7	C1B—C4B—H4D	113.6
C3A—C4A—H4B	113.7	C3B—C4B—H4D	113.6
H4A—C4A—H4B	110.9	H4C—C4B—H4D	110.9
C10A—C5A—C6A	117.4 (3)	C10B—C5B—C6B	117.9 (3)
C10A—C5A—C3A	120.6 (3)	C10B—C5B—C3B	121.5 (3)
C6A—C5A—C3A	121.9 (3)	C6B—C5B—C3B	120.5 (3)
C7A—C6A—C5A	119.4 (4)	C7B—C6B—C5B	119.0 (4)
C7A—C6A—C11A	117.1 (4)	C7B—C6B—C11B	117.8 (3)
C5A—C6A—C11A	123.4 (4)	C5B—C6B—C11B	123.2 (3)
C8A—C7A—C6A	123.8 (4)	C8B—C7B—C6B	123.1 (4)
C8A—C7A—H7A	118.1	C8B—C7B—H7B	118.5
C6A—C7A—H7A	118.1	C6B—C7B—H7B	118.5
C7A—C8A—C9A	116.4 (4)	C9B—C8B—C7B	117.3 (4)
C7A—C8A—C12A	122.2 (4)	C9B—C8B—C12B	122.3 (5)
C9A—C8A—C12A	121.4 (5)	C7B—C8B—C12B	120.3 (5)
C8A—C9A—C10A	122.8 (4)	C8B—C9B—C10B	123.1 (4)
C8A—C9A—H9A	118.6	C8B—C9B—H9B	118.4
C10A—C9A—H9A	118.6	C10B—C9B—H9B	118.4
C9A—C10A—C5A	120.2 (3)	C9B—C10B—C5B	119.5 (3)
C9A—C10A—C13A	116.1 (4)	C9B—C10B—C13B	117.3 (4)
C5A—C10A—C13A	123.7 (3)	C5B—C10B—C13B	123.1 (3)
C6A—C11A—H11A	109.5	C6B—C11B—H11D	109.5
C6A—C11A—H11B	109.5	C6B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
C6A—C11A—H11C	109.5	C6B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
C8A—C12A—H12A	109.5	C8B—C12B—H12D	109.5
C8A—C12A—H12B	109.5	C8B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C8A—C12A—H12C	109.5	C8B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C10A—C13A—H13A	109.5	C10B—C13B—H13D	109.5
C10A—C13A—H13B	109.5	C10B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C10A—C13A—H13C	109.5	C10B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C3A—C14A—H14A	109.5	C3B—C14B—H14D	109.5
C3A—C14A—H14B	109.5	C3B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C3A—C14A—H14C	109.5	C3B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C16A—C15A—N1A	111.9 (3)	C16B—C15B—N1B	114.6 (3)
C16A—C15A—C1A	124.9 (3)	C16B—C15B—C1B	127.2 (3)
N1A—C15A—C1A	123.2 (3)	N1B—C15B—C1B	118.1 (3)
C15A—C16A—S1A	113.6 (2)	C15B—C16B—S1B	111.5 (2)
C15A—C16A—H16A	123.2	C15B—C16B—H16B	124.2
S1A—C16A—H16A	123.2	S1B—C16B—H16B	124.2
N2A—C17A—N1A	124.5 (3)	N1B—C17B—N2B	122.7 (3)
N2A—C17A—S1A	123.5 (2)	N1B—C17B—S1B	114.5 (2)
N1A—C17A—S1A	112.0 (2)	N2B—C17B—S1B	122.8 (2)
N3A—C18A—C19A	120.6 (3)	N3B—C18B—C19B	121.0 (3)
N3A—C18A—H18A	119.7	N3B—C18B—H18B	119.5
C19A—C18A—H18A	119.7	C19B—C18B—H18B	119.5
C20A—C19A—C24A	118.8 (3)	C20B—C19B—C24B	118.4 (3)
C20A—C19A—C18A	119.5 (3)	C20B—C19B—C18B	119.4 (2)
C24A—C19A—C18A	121.7 (3)	C24B—C19B—C18B	122.2 (3)
C21A—C20A—C19A	120.4 (3)	C21B—C20B—C19B	120.5 (3)
C21A—C20A—H20A	119.8	C21B—C20B—H20B	119.7
C19A—C20A—H20A	119.8	C19B—C20B—H20B	119.7
C20A—C21A—C22A	120.5 (4)	C20B—C21B—C22B	120.6 (3)
C20A—C21A—Br1A	120.7 (3)	C20B—C21B—Br1B	120.3 (2)
C22A—C21A—Br1A	118.8 (3)	C22B—C21B—Br1B	119.0 (2)
C23A—C22A—C21A	120.2 (3)	C23B—C22B—C21B	119.6 (3)
C23A—C22A—H22A	119.9	C23B—C22B—H22B	120.2
C21A—C22A—H22A	119.9	C21B—C22B—H22B	120.2
C22A—C23A—C24A	120.7 (4)	C22B—C23B—C24B	120.7 (3)
C22A—C23A—H23A	119.7	C22B—C23B—H23B	119.7
C24A—C23A—H23A	119.7	C24B—C23B—H23B	119.7
O1A—C24A—C23A	118.0 (3)	O1B—C24B—C23B	117.7 (3)
O1A—C24A—C19A	122.5 (3)	O1B—C24B—C19B	122.2 (3)
C23A—C24A—C19A	119.4 (3)	C23B—C24B—C19B	120.1 (3)
C17A—N2A—N3A—C18A	172.3 (3)	C17B—N2B—N3B—C18B	−179.1 (3)
C15A—C1A—C2A—C3A	144.1 (3)	C15B—C1B—C2B—C3B	−144.8 (3)
C4A—C1A—C2A—C3A	19.2 (2)	C4B—C1B—C2B—C3B	−21.3 (2)
C1A—C2A—C3A—C5A	−137.6 (3)	C1B—C2B—C3B—C5B	142.3 (3)
C1A—C2A—C3A—C14A	93.9 (3)	C1B—C2B—C3B—C14B	−89.2 (3)
C1A—C2A—C3A—C4A	−18.7 (2)	C1B—C2B—C3B—C4B	21.0 (2)
C15A—C1A—C4A—C3A	−137.0 (3)	C15B—C1B—C4B—C3B	144.3 (3)
C2A—C1A—C4A—C3A	−19.0 (2)	C2B—C1B—C4B—C3B	21.3 (2)
C5A—C3A—C4A—C1A	140.1 (3)	C5B—C3B—C4B—C1B	−141.9 (3)
C14A—C3A—C4A—C1A	−91.5 (3)	C14B—C3B—C4B—C1B	90.0 (3)
C2A—C3A—C4A—C1A	18.8 (2)	C2B—C3B—C4B—C1B	−21.0 (2)
C14A—C3A—C5A—C10A	−82.0 (4)	C14B—C3B—C5B—C10B	89.0 (4)
C2A—C3A—C5A—C10A	149.1 (3)	C2B—C3B—C5B—C10B	−141.6 (3)
C4A—C3A—C5A—C10A	47.8 (4)	C4B—C3B—C5B—C10B	−39.8 (4)
C14A—C3A—C5A—C6A	94.2 (4)	C14B—C3B—C5B—C6B	−87.2 (4)
C2A—C3A—C5A—C6A	−34.7 (4)	C2B—C3B—C5B—C6B	42.3 (4)
C4A—C3A—C5A—C6A	−136.1 (3)	C4B—C3B—C5B—C6B	144.0 (3)
C10A—C5A—C6A—C7A	−2.6 (5)	C10B—C5B—C6B—C7B	2.9 (5)
C3A—C5A—C6A—C7A	−178.9 (3)	C3B—C5B—C6B—C7B	179.2 (3)
C10A—C5A—C6A—C11A	174.7 (3)	C10B—C5B—C6B—C11B	−175.7 (3)
C3A—C5A—C6A—C11A	−1.6 (5)	C3B—C5B—C6B—C11B	0.6 (5)
C5A—C6A—C7A—C8A	1.0 (5)	C5B—C6B—C7B—C8B	−1.0 (6)
C11A—C6A—C7A—C8A	−176.5 (4)	C11B—C6B—C7B—C8B	177.8 (4)
C6A—C7A—C8A—C9A	0.4 (6)	C6B—C7B—C8B—C9B	−1.6 (6)
C6A—C7A—C8A—C12A	178.5 (4)	C6B—C7B—C8B—C12B	179.5 (4)
C7A—C8A—C9A—C10A	0.1 (6)	C7B—C8B—C9B—C10B	2.3 (7)
C12A—C8A—C9A—C10A	−178.1 (4)	C12B—C8B—C9B—C10B	−178.9 (4)
C8A—C9A—C10A—C5A	−1.8 (5)	C8B—C9B—C10B—C5B	−0.3 (6)
C8A—C9A—C10A—C13A	174.9 (4)	C8B—C9B—C10B—C13B	−179.2 (4)
C6A—C5A—C10A—C9A	3.0 (5)	C6B—C5B—C10B—C9B	−2.4 (5)
C3A—C5A—C10A—C9A	179.4 (3)	C3B—C5B—C10B—C9B	−178.6 (3)
C6A—C5A—C10A—C13A	−173.5 (3)	C6B—C5B—C10B—C13B	176.6 (3)
C3A—C5A—C10A—C13A	2.9 (5)	C3B—C5B—C10B—C13B	0.3 (5)
C17A—N1A—C15A—C16A	−0.9 (4)	C17B—N1B—C15B—C16B	−0.7 (4)
C17A—N1A—C15A—C1A	−178.7 (3)	C17B—N1B—C15B—C1B	178.5 (3)
C4A—C1A—C15A—C16A	122.4 (4)	C2B—C1B—C15B—C16B	62.1 (5)
C2A—C1A—C15A—C16A	18.4 (5)	C4B—C1B—C15B—C16B	−43.0 (5)
C4A—C1A—C15A—N1A	−60.1 (5)	C2B—C1B—C15B—N1B	−117.0 (3)
C2A—C1A—C15A—N1A	−164.1 (3)	C4B—C1B—C15B—N1B	137.9 (3)
N1A—C15A—C16A—S1A	0.6 (4)	N1B—C15B—C16B—S1B	0.1 (4)
C1A—C15A—C16A—S1A	178.3 (3)	C1B—C15B—C16B—S1B	−179.1 (3)
C17A—S1A—C16A—C15A	−0.1 (3)	C17B—S1B—C16B—C15B	0.4 (3)
N3A—N2A—C17A—N1A	174.0 (3)	C15B—N1B—C17B—N2B	179.7 (3)
N3A—N2A—C17A—S1A	−6.5 (4)	C15B—N1B—C17B—S1B	1.1 (3)
C15A—N1A—C17A—N2A	−179.5 (3)	N3B—N2B—C17B—N1B	168.7 (3)
C15A—N1A—C17A—S1A	0.9 (4)	N3B—N2B—C17B—S1B	−12.9 (4)
C16A—S1A—C17A—N2A	180.0 (3)	C16B—S1B—C17B—N1B	−0.9 (3)
C16A—S1A—C17A—N1A	−0.5 (3)	C16B—S1B—C17B—N2B	−179.5 (3)
N2A—N3A—C18A—C19A	175.5 (3)	N2B—N3B—C18B—C19B	177.7 (3)
N3A—C18A—C19A—C20A	179.5 (3)	N3B—C18B—C19B—C20B	−178.7 (3)
N3A—C18A—C19A—C24A	−1.8 (5)	N3B—C18B—C19B—C24B	1.0 (5)
C24A—C19A—C20A—C21A	−0.7 (5)	C24B—C19B—C20B—C21B	1.1 (4)
C18A—C19A—C20A—C21A	178.0 (3)	C18B—C19B—C20B—C21B	−179.2 (3)
C19A—C20A—C21A—C22A	0.4 (6)	C19B—C20B—C21B—C22B	−0.4 (5)
C19A—C20A—C21A—Br1A	179.6 (3)	C19B—C20B—C21B—Br1B	179.8 (2)
C20A—C21A—C22A—C23A	−0.3 (6)	C20B—C21B—C22B—C23B	−0.5 (5)
Br1A—C21A—C22A—C23A	−179.6 (3)	Br1B—C21B—C22B—C23B	179.4 (2)
C21A—C22A—C23A—C24A	0.6 (6)	C21B—C22B—C23B—C24B	0.6 (5)
C22A—C23A—C24A—O1A	179.5 (3)	C22B—C23B—C24B—O1B	179.9 (3)
C22A—C23A—C24A—C19A	−1.0 (6)	C22B—C23B—C24B—C19B	0.2 (5)
C20A—C19A—C24A—O1A	−179.5 (3)	C20B—C19B—C24B—O1B	179.2 (3)
C18A—C19A—C24A—O1A	1.9 (5)	C18B—C19B—C24B—O1B	−0.4 (5)
C20A—C19A—C24A—C23A	1.0 (5)	C20B—C19B—C24B—C23B	−1.0 (4)
C18A—C19A—C24A—C23A	−177.6 (3)	C18B—C19B—C24B—C23B	179.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1N···N1B	0.86	2.17	2.979 (3)	158
O1A—H1O···N3A	0.82	1.89	2.613 (3)	146
N2B—H2N···N2A	0.86	2.21	2.880 (4)	134
O1B—H2O···N3B	0.82	1.91	2.635 (3)	146
C12A—H12C···Cg1^i	0.96	2.74	3.627 (3)	154

Symmetry code: (i) −x, −y+2, −z+1.