Crystal structure of a new hybrid anti-mony-halide-based compound for possible non-linear optical applications.

The hybrid title compound, catena-poly[[[bis-(1,4-diazo-niabi-cyclo-[2.2.2]octa-ne) [tetra-achlorido-anti-monate(III)]-μ-chlorido-[tetra-chlorido-anti-monate(III)]-μ-chlorido]] monohydrate], {(C6H14N2)2[Sb2Cl10]·H2O} n , is self-assembled into alternating organic and inorganic layers parallel to the bc plane. The anionic inorganic layer consists of infinite zigzag chains of corner-sharing [SbCl6](3-) octa-hedra running along the b axis. The organic part is made up of 1,4-diazo-niabi-cyclo-[2.2.2]octane dications (dabcoH2 (2+)). The water mol-ecules in the structure connect inorganic and organic layers. Hydrogen-bonding inter-actions between the ammonium groups, water mol-ecules and Cl atoms ensure the structure cohesion.

Chemical context

Organic–inorganic hybrid structures with the general formula {(R a)n+ M b X 3b+na} (where R is an organic cation; M is any trivalent metal and X is Cl, Br or/and I) are able to combine desirable characteristics from both types of constituents into a mol­ecular scale composite. These hybrids have been extensively studied for their excitonic and magneto-optical properties. In recent years, a significant number of organic–inorganic hybrid materials based on anti­mony–halide units have been studied. Six-coordinate anti­mony halides can arrange themselves in three-, two- or one-dimensional networks through sharing halides in the SbX 6 octa­hedra, separated by organic cations (Ben Rhaiem et al., 2013 ▸; Leblanc et al., 2012 ▸; Piecha et al., 2012 ▸; Bujack & Angel, 2005 ▸, 2006 ▸; Bujack & Zaleski, 2004 ▸). One-dimensional extended chains can be formed by one, two or three bridging halides and combinations thereof. The use of one bridging halide leads to two types of chains; if the two bridging halides connecting the central octa­hedron to its neighbours are related cis, a zigzag pattern is obtained; if they are trans, the chain is linear.

Structural commentary

The asymmetric unit of the new chlorido­anti­monate(III) compound, (C6H14N2)2[Sb2Cl10]·H2O, (I), consists of two symmetry-independant (dabcoH2)2+ dications, a corner sharing bi-octa­hedron deca­chlorido­dianti­monate(III) anion and one crystallization water mol­ecule. The cations are labeled Cat1 (containing atoms N1 and N2) and Cat2 (containing N3 and N4) and the atomic numbering scheme is shown in Fig. 1 ▸.

Figure 1

The asymmetric unit of (I) completed by Cl4i, showing the atomic numbering scheme. Displacement ellipsoids are shown at 30% probability level. [Symmetry code: (i) x, y − 1, z.]

The structure of the title compound, (I), is self-assembled into an alternating organic and inorganic layered structure. The anionic layer consists of infinite zigzag chains of corner-sharing [SbCl6]3− octa­hedra running along the b axis. Thus, (I) can be classified among the one-dimensional hybrid structures. The organic part is made up of (dabcoH2)2+ cations located in the holes around the corner-sharing octa­hedra. The layers are stacked along the a axis and water mol­ecules connect the organic and inorganic components (Fig. 2 ▸).

Figure 2

The organic–inorganic layered structure of (I), projected along the c axis, showing the zigzag chains of corner-sharing [SbCl6]3− octa­hedra.

The inorganic structural unit part of (I) is build up by two Sb atoms in an octa­hedral coordination ([Sb1Cl6]3− and [Sb2Cl6]3−) joined by the Cl2 ion. Both octa­hedra are severely distorted with Sb—Cl bond lengths lying in the range of 2.5233 (18)–3.073 (2) Å for the bridging ones and 2.4277 (15)–2.8233 (17) Å for the terminal ones. The two bridging halides (Cl2 and Cl4) connecting the central octa­hedron to its neighbours are related cis, leading to zigzag chain of corner-sharing [SbCl6]3− octa­hedra running along the b axis (Fig. 3 ▸).

Figure 3

A magnified view of the hydrogen bonding of the inorganic chain in (I). H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) x, y − 1, z; (ii) x, y + 1, z; (iii) −x + 1, −y + 1, z + ; (iv) −x + 1, −y + 1, z − ; (v) −x + , y − , z − .]

It is worth noting that at room temperature the DABCO mol­ecule crystallizes in the hexa­gonal system (P63/m) (Nimmo & Lucas, 1976 ▸). In our case, Cat2 seems to be more distorted than Cat1. In fact, the highest absolute value of the N—C—C—N torsion angle of 7.80 (14)° proves that both (dabcoH2)2+ cations exhibit deviations from ideal D 3 symmetry. The observed lowering symmetry (hexa­gonal to ortho­rhom­bic) is probably due to the distortion of the (dabcoH2)2+ cation and can be related to the complex hydrogen-bond network linking the mol­ecular components (cations, anions and water mol­ecules).

The studied compound crystals are transparent and the structure is noncentrosymmetric (Pna21). These are two indispensable conditions making this phase a potential promising candidate for non-linear optical (NLO) behaviour as is the case for the well-known KTiOPO4 (KTP) and equivalent efficient NLO materials.

Supra­molecular features

As shown in Fig. 3 ▸, every bi-octa­hedron unit is linked to four (dabcoH2)2+ cations and two water mol­ecules via hydrogen bonds (Table 1 ▸): on one side Cat1 via Cl6⋯H1iv—N1iv and Cat 2 by Cl8⋯H3v—N3v, Cl9⋯H3v—N3v [symmetry codes: (iv) −x + 1, −y + 1, −z − ; (v) −x + , y − , z − ] and the other side Cat1 via Cl1⋯H2iii—N2iii, Cl3⋯H2iii—N2iii and Cat2 by Cl3⋯H4ii—N4ii [symmetry codes: (ii) x, y + 1, z; (iii) −x + 1, −y + 1, z + ]. The water mol­ecules are linked by Cl5⋯H13A—O and Cl9⋯H13B v—Ov [symmetry code: (v) −x + , y − , z − ].

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1Cl6i	0.95	2.67	3.391(6)	134
N2H2Cl1ii	0.88	2.78	3.378(4)	126
N2H2Cl3ii	0.88	2.62	3.281(6)	133
N2H2Oii	0.88	2.46	3.040(7)	124
N3H3Cl8iii	0.89	2.82	3.418(7)	126
N3H3Cl9iii	0.89	2.38	3.132(9)	143
N4H4Cl3iv	0.87	2.66	3.303(6)	131
N4H4Oiv	0.87	2.30	3.026(8)	143
OH13ACl5	0.84	2.43	3.185(7)	151
OH13BCl9iii	0.83	2.66	3.210(5)	126

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Using ammonium groups, both cations (Cat1 and Cat2) are linked to the anionic chains by hydrogen bonds via halogenous octa­hedral vertices. As shown in Fig. 4 ▸, Cat1 is linked by N1—H1⋯Cl6i hydrogen bond and three inter­actions between N2—H2 group, both vertices Cl1ii—Sb1ii, Cl3ii—Sb1ii and O atom of the water mol­ecule [symmetry codes: (i) −x + 1, −y + 1, z + ; (ii) −x + 1, −y + 1, z − ]. On the other hand, each ammonium group of Cat 2 inter­acts by two hydrogen bonds. N4—H4 to Cl3i—Sb1i and the O atom and N3—H3 group to both Cl8ii—Sb2ii and Cl9ii—Sb2ii vertices (Fig. 5 ▸) [symmetry codes: (i) x, y − 1, z; (ii) −x + , y + , z + ].

Figure 4

The hydrogen-bonding environment of Cat 1 in (I). Only H atoms involved in hydrogen bonding have been represented. [Symmetry codes: (i) −x + 1, −y + 1, z + ; (ii) −x + 1, −y + 1, z − .]

Figure 5

The hydrogen-bonding environment of Cat 2 in (I). Only H atoms involved in hydrogen bonding have been represented. [Symmetry codes: (i) x, y − 1, z; (ii) −x + , y + , z + .]

As can be seen in Fig. 6 ▸, the water mol­ecule plays an important role in the structure connectivity. It is establishing four hydrogen links joining Cat1 by O⋯H2ii—N2ii, Cat2 through O⋯H4i—N4i and two [SbCl6]3− octa­hedra via O—H13A⋯Cl5 and O—H13B⋯Cl9iii [symmetry codes: (i) x, y + 1, z; (ii) −x + 1, −y + 1, z + ; (iii) −x + , y + , z + ].

Figure 6

Water-mol­ecule hydrogen-bonding inter­actions in (I). C—H bonds have been omitted for clarity. [Symmetry codes: (i) x, y + 1, z; (ii) −x + 1, −y + 1, z + ; (iii) −x + , y + , z + .]

Database survey

A search of the Cambridge Structural Database (Version 5.36; Groom & Allen, 2014 ▸) gave 184 hits for organic–inorganic hybrid materials based on anti­mony chloride units. For this class of compounds with (dabcoH2)2+ cations, there is only one zero-dimensional compound, (C6H14N2)2[Sb2Cl10]·2H2O containing isolated [Sb2Cl10]4− double octa­hedra, (dabcoH2)2+ cations and water mol­ecules (Ben Rhaiem et al., 2013 ▸). Indeed, this compound is a pseudo-polymorph over the title compound. For similar one-dimensional compounds with N,N-di­methyl­ethylenedi­ammonium cations, [(CH3)2NH(CH2)2NH3]2+, see: Bujack & Angel (2006 ▸). For two-dimensional compounds with [{Sb2Cl9}]3 polyanionic layers, see: Bujack & Angel (2005 ▸); Bujack & Zaleski (2004 ▸).

Synthesis and crystallization

A mixture of SbCl3 (1 mmol) and DABCO (0.5 mmol) was dissolved in a hydro­chloric aqueous solution and stirred for several minutes at 353 K. Colourless crystals suitable for X-ray diffraction analysis were obtained by slow evaporation at room temperature after two weeks.

Refinement

Data collection and structure refinement details are summarized in Table 2 ▸. H atoms were localized from geometrical constraint conditions using adequate AFIX and DFIX SHELXL (Sheldrick, 2008 ▸) options and parameters were refined with a common isotropic displacement parameter. Water H atoms were found in difference Fourier maps and O—H distances were refined using DFIX and DANG soft restraints. The Flack parameter was refined despite the low Friedel pair coverage because the structure contains a sufficient number of relatively strong anomalous scatterers.

Table 2

Experimental details

Crystal data
Chemical formula	(C6H14N2)2[Sb2Cl10]H2O
M r	844.40
Crystal system, space group	Orthorhombic, P n a21
Temperature (K)	298
a, b, c ()	29.122(3), 8.4029(10), 11.358(2)
V (3)	2779.4(7)
Z	4
Radiation type	Mo K
(mm1)	2.92
Crystal size (mm)	0.13 0.06 0.02
Data collection
Diffractometer	EnrafNonius CAD-4
Absorption correction	scan (North et al., 1968 ▸)
T min, T max	0.358, 0.555
No. of measured, independent and observed [I > 2(I)] reflections	7000, 3492, 2988
R int	0.041
(sin /)max (1)	0.638
Refinement
R[F 2 > 2(F 2)], wR(F 2), S	0.026, 0.070, 1.09
No. of reflections	3492
No. of parameters	273
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
max, min (e 3)	0.72, 0.62
Absolute structure	Flack (1983 ▸), 66 Friedel pairs
Absolute structure parameter	0.01(3)

Computer programs: CAD-4 EXPRESS (Duisenberg, 1992 ▸), XCAD4 (Harms Wocadlo, 1995 ▸), SHELXS97 and SHELXL97 (Sheldrick, 2008 ▸), DIAMOND (Brandenburg, 2006 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015007379/vn2091sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007379/vn2091Isup2.hkl

CCDC reference: 943047

Additional supporting information: crystallographic information; 3D view; checkCIF report

(C6H14N2)2[Sb2Cl10]·H2O	Dx = 2.018 Mg m−3
Mr = 844.40	Melting point: 594 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3492 reflections
a = 29.122 (3) Å	θ = 2.4–27.0°
b = 8.4029 (10) Å	µ = 2.92 mm−1
c = 11.358 (2) Å	T = 298 K
V = 2779.4 (7) Å3	Prism, colourless
Z = 4	0.13 × 0.06 × 0.02 mm
F(000) = 1640

Enraf–Nonius CAD-4 diffractometer	2988 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
Graphite monochromator	θmax = 27.0°, θmin = 2.3°
non–profiled ω/2θ scans	h = −37→1
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.358, Tmax = 0.555	l = −1→14
7000 measured reflections	2 standard reflections every 120 min
3492 independent reflections	intensity decay: −1%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.026	w = 1/[σ2(Fo2) + (0.0316P)2 + 2.3277P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.070	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.72 e Å−3
3492 reflections	Δρmin = −0.62 e Å−3
273 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
5 restraints	Extinction coefficient: 0.00168 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 66 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.01 (3)

Experimental. Absorption correction: North et al. (1968) Number of psi-scan sets used was 6 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Sb1	0.593657 (12)	0.74481 (3)	0.49688 (3)	0.02787 (11)
Sb2	0.657146 (11)	0.24077 (3)	0.22050 (3)	0.02842 (11)
Cl1	0.57361 (5)	0.54093 (18)	0.66622 (15)	0.0452 (4)
Cl2	0.61712 (8)	0.5151 (2)	0.3671 (2)	0.0760 (6)
Cl3	0.57606 (5)	0.97355 (17)	0.67100 (15)	0.0437 (3)
Cl4	0.61408 (7)	0.9753 (2)	0.3459 (2)	0.0765 (6)
Cl5	0.67713 (6)	0.75095 (17)	0.56999 (19)	0.0522 (4)
Cl6	0.50864 (7)	0.7328 (2)	0.3883 (2)	0.0619 (5)
Cl7	0.69068 (7)	0.4519 (2)	0.09980 (17)	0.0645 (5)
Cl8	0.68555 (6)	0.0345 (2)	0.08973 (16)	0.0562 (5)
Cl9	0.74068 (5)	0.19561 (18)	0.34215 (18)	0.0430 (3)
Cl10	0.58708 (5)	0.25828 (14)	0.1013 (2)	0.0478 (4)
N1	0.49311 (19)	0.2444 (5)	0.5900 (5)	0.0390 (12)
H1	0.5113 (15)	0.2480 (6)	0.659 (6)	0.047*
N2	0.44602 (17)	0.2354 (5)	0.4084 (5)	0.0378 (11)
H2	0.4294 (4)	0.2318 (5)	0.3440 (16)	0.045*
N3	0.72003 (16)	0.3837 (5)	0.7294 (5)	0.0389 (11)
H3	0.7352 (10)	0.475 (6)	0.7261 (5)	0.047*
N4	0.6767 (2)	0.1317 (6)	0.7367 (7)	0.068 (2)
H4	0.6616 (14)	0.044 (8)	0.7384 (7)	0.082*
C1	0.5235 (2)	0.2498 (6)	0.4859 (7)	0.0455 (16)
H1A	0.5447	0.1609	0.4882	0.055*
H1B	0.5412	0.3475	0.4867	0.055*
C2	0.4952 (2)	0.2417 (8)	0.3748 (8)	0.059 (2)
H2A	0.5010	0.3347	0.3264	0.071*
H2B	0.5033	0.1476	0.3299	0.071*
C3	0.4365 (2)	0.0911 (7)	0.4788 (6)	0.0481 (17)
H3A	0.4434	−0.0030	0.4326	0.058*
H3B	0.4043	0.0880	0.5001	0.058*
C4	0.4656 (2)	0.0921 (7)	0.5887 (6)	0.0479 (15)
H4A	0.4860	0.0010	0.5891	0.057*
H4B	0.4461	0.0865	0.6579	0.057*
C5	0.4622 (2)	0.3851 (8)	0.5871 (6)	0.0510 (16)
H5A	0.4802	0.4821	0.5888	0.061*
H5B	0.4423	0.3844	0.6556	0.061*
C6	0.4333 (2)	0.3800 (6)	0.4754 (6)	0.0467 (17)
H6A	0.4010	0.3773	0.4953	0.056*
H6B	0.4391	0.4742	0.4283	0.056*
C7	0.7097 (3)	0.3302 (8)	0.6095 (6)	0.063 (2)
H7A	0.7381	0.3127	0.5668	0.075*
H7B	0.6924	0.4116	0.5685	0.075*
C8	0.6829 (4)	0.1808 (11)	0.6134 (8)	0.092 (4)
H8A	0.6532	0.1972	0.5767	0.110*
H8B	0.6989	0.0981	0.5702	0.110*
C9	0.6768 (2)	0.4080 (7)	0.7935 (7)	0.0473 (15)
H9A	0.6577	0.4839	0.7516	0.057*
H9B	0.6831	0.4505	0.8712	0.057*
C10	0.6519 (2)	0.2512 (6)	0.8042 (8)	0.0479 (18)
H10A	0.6502	0.2195	0.8862	0.057*
H10B	0.6208	0.2617	0.7744	0.057*
C11	0.7484 (3)	0.2641 (9)	0.7941 (10)	0.081 (3)
H11A	0.7525	0.2964	0.8754	0.097*
H11B	0.7784	0.2535	0.7577	0.097*
C12	0.7221 (3)	0.1056 (10)	0.7878 (11)	0.107 (4)
H12A	0.7391	0.0303	0.7399	0.129*
H12B	0.7190	0.0612	0.8662	0.129*
O	0.65412 (17)	0.8095 (7)	0.8407 (6)	0.0637 (14)
H13A	0.662 (3)	0.760 (8)	0.780 (4)	0.070*
H13B	0.674 (2)	0.788 (9)	0.890 (5)	0.070*

	U11	U22	U33	U12	U13	U23
Sb1	0.0343 (2)	0.02365 (18)	0.0257 (2)	−0.00135 (12)	0.00135 (16)	−0.00099 (18)
Sb2	0.03007 (18)	0.02876 (19)	0.0264 (2)	0.00021 (12)	−0.00028 (17)	−0.0021 (2)
Cl1	0.0497 (9)	0.0439 (7)	0.0421 (8)	−0.0053 (6)	−0.0007 (7)	−0.0001 (7)
Cl2	0.0915 (15)	0.0703 (11)	0.0662 (14)	0.0140 (11)	0.0062 (12)	−0.0308 (11)
Cl3	0.0418 (8)	0.0419 (7)	0.0473 (8)	0.0013 (6)	−0.0043 (7)	0.0077 (7)
Cl4	0.0833 (14)	0.0808 (13)	0.0655 (14)	−0.0231 (11)	−0.0066 (13)	0.0276 (12)
Cl5	0.0457 (8)	0.0532 (9)	0.0578 (12)	−0.0055 (7)	0.0018 (8)	0.0039 (8)
Cl6	0.0538 (10)	0.0626 (11)	0.0695 (14)	−0.0031 (8)	0.0168 (10)	0.0005 (10)
Cl7	0.0750 (12)	0.0718 (11)	0.0466 (10)	−0.0361 (9)	−0.0079 (10)	0.0184 (9)
Cl8	0.0638 (11)	0.0643 (9)	0.0406 (9)	0.0285 (8)	−0.0105 (8)	−0.0222 (8)
Cl9	0.0429 (7)	0.0501 (7)	0.0360 (7)	0.0012 (7)	0.0007 (7)	−0.0113 (7)
Cl10	0.0447 (8)	0.0333 (7)	0.0652 (12)	0.0041 (5)	−0.0225 (8)	−0.0034 (7)
N1	0.044 (3)	0.038 (3)	0.035 (3)	0.001 (2)	−0.007 (2)	0.000 (2)
N2	0.039 (3)	0.036 (2)	0.038 (3)	0.0019 (18)	−0.007 (2)	0.003 (2)
N3	0.046 (3)	0.033 (2)	0.038 (3)	−0.0052 (18)	0.004 (3)	−0.003 (2)
N4	0.089 (5)	0.028 (2)	0.088 (5)	−0.010 (3)	0.049 (4)	0.000 (3)
C1	0.034 (3)	0.041 (3)	0.062 (5)	−0.004 (2)	0.004 (3)	0.003 (3)
C2	0.045 (4)	0.089 (6)	0.043 (4)	−0.001 (3)	0.003 (3)	−0.001 (4)
C3	0.057 (4)	0.031 (2)	0.057 (4)	−0.008 (2)	−0.021 (4)	0.009 (3)
C4	0.053 (4)	0.046 (3)	0.044 (4)	−0.011 (3)	−0.002 (3)	0.013 (3)
C5	0.055 (4)	0.051 (3)	0.047 (4)	0.012 (3)	0.000 (3)	−0.009 (3)
C6	0.057 (4)	0.032 (3)	0.051 (4)	0.010 (3)	−0.014 (3)	−0.004 (3)
C7	0.110 (7)	0.051 (3)	0.026 (3)	−0.031 (4)	0.009 (4)	−0.004 (3)
C8	0.133 (9)	0.087 (6)	0.054 (5)	−0.071 (6)	0.028 (6)	−0.035 (5)
C9	0.052 (4)	0.038 (3)	0.052 (4)	0.002 (3)	0.008 (3)	−0.015 (3)
C10	0.047 (4)	0.051 (4)	0.046 (4)	0.004 (3)	0.017 (3)	0.004 (3)
C11	0.056 (5)	0.111 (7)	0.075 (7)	0.033 (5)	−0.011 (5)	−0.004 (5)
C12	0.103 (8)	0.071 (5)	0.148 (10)	0.047 (5)	0.079 (7)	0.060 (6)
O	0.055 (3)	0.067 (3)	0.069 (4)	0.017 (2)	−0.010 (3)	−0.016 (3)

Sb1—Cl2	2.5233 (18)	C1—H1B	0.9700
Sb1—Cl5	2.5695 (18)	C2—H2A	0.9700
Sb1—Cl1	2.6411 (17)	C2—H2B	0.9700
Sb1—Cl4	2.654 (2)	C3—C4	1.507 (9)
Sb1—Cl6	2.768 (2)	C3—H3A	0.9700
Sb1—Cl3	2.8051 (17)	C3—H3B	0.9700
Sb2—Cl8	2.4277 (15)	C4—H4A	0.9700
Sb2—Cl7	2.4457 (17)	C4—H4B	0.9700
Sb2—Cl10	2.4532 (16)	C5—C6	1.521 (9)
Sb2—Cl9	2.8233 (17)	C5—H5A	0.9700
Sb2—Cl2	3.073 (2)	C5—H5B	0.9700
Sb2—Cl4i	2.9291 (19)	C6—H6A	0.9700
N1—C1	1.477 (9)	C6—H6B	0.9700
N1—C5	1.487 (8)	C7—C8	1.480 (10)
N1—C4	1.510 (7)	C7—H7A	0.9700
N1—H1	0.9496	C7—H7B	0.9700
N2—C3	1.478 (7)	C8—H8A	0.9700
N2—C6	1.481 (7)	C8—H8B	0.9700
N2—C2	1.483 (9)	C9—C10	1.509 (7)
N2—H2	0.8784	C9—H9A	0.9700
N3—C7	1.465 (8)	C9—H9B	0.9700
N3—C9	1.469 (8)	C10—H10A	0.9700
N3—C11	1.494 (9)	C10—H10B	0.9700
N3—H3	0.8858	C11—C12	1.538 (11)
N4—C10	1.456 (8)	C11—H11A	0.9700
N4—C12	1.462 (12)	C11—H11B	0.9700
N4—C8	1.471 (11)	C12—H12A	0.9700
N4—H4	0.8565	C12—H12B	0.9700
C1—C2	1.508 (11)	O—H13A	0.84 (2)
C1—H1A	0.9700	O—H13B	0.82 (2)
Cl2—Sb1—Cl5	87.02 (7)	C1—C2—H2B	110.0
Cl2—Sb1—Cl1	89.38 (7)	H2A—C2—H2B	108.4
Cl5—Sb1—Cl1	89.25 (6)	N2—C3—C4	109.8 (5)
Cl2—Sb1—Cl4	96.90 (9)	N2—C3—H3A	109.7
Cl5—Sb1—Cl4	88.98 (6)	C4—C3—H3A	109.7
Cl1—Sb1—Cl4	173.38 (6)	N2—C3—H3B	109.7
Cl2—Sb1—Cl6	87.36 (7)	C4—C3—H3B	109.7
Cl5—Sb1—Cl6	172.33 (7)	H3A—C3—H3B	108.2
Cl1—Sb1—Cl6	95.92 (6)	C3—C4—N1	108.1 (5)
Cl4—Sb1—Cl6	86.51 (6)	C3—C4—H4A	110.1
Cl2—Sb1—Cl3	170.28 (7)	N1—C4—H4A	110.1
Cl5—Sb1—Cl3	86.05 (5)	C3—C4—H4B	110.1
Cl1—Sb1—Cl3	83.72 (5)	N1—C4—H4B	110.1
Cl4—Sb1—Cl3	89.79 (6)	H4A—C4—H4B	108.4
Cl6—Sb1—Cl3	100.12 (5)	N1—C5—C6	109.3 (5)
Cl8—Sb2—Cl7	92.23 (8)	N1—C5—H5A	109.8
Cl8—Sb2—Cl10	89.35 (6)	C6—C5—H5A	109.8
Cl7—Sb2—Cl10	88.82 (7)	N1—C5—H5B	109.8
Cl8—Sb2—Cl9	84.83 (5)	C6—C5—H5B	109.8
Cl7—Sb2—Cl9	91.59 (6)	H5A—C5—H5B	108.3
Cl10—Sb2—Cl9	174.17 (6)	N2—C6—C5	108.3 (5)
Cl4i—Sb2—Cl10	87.62 (5)	N2—C6—H6A	110.0
Cl2—Sb2—Cl10	86.49 (6)	C5—C6—H6A	110.0
Cl4i—Sb2—Cl9	91.63 (5)	N2—C6—H6B	110.0
Cl2—Sb2—Cl9	99.35 (5)	C5—C6—H6B	110.0
Cl8—Sb2—Cl4i	84.24 (6)	H6A—C6—H6B	108.4
Cl4i—Sb2—Cl2	98.36 (5)	N3—C7—C8	109.9 (6)
Cl2—Sb2—Cl7	84.89 (6)	N3—C7—H7A	109.7
Cl2—Sb2—Cl8	174.98 (6)	C8—C7—H7A	109.7
Cl4i—Sb2—Cl7	175.00 (6)	N3—C7—H7B	109.7
C1—N1—C5	108.7 (5)	C8—C7—H7B	109.7
C1—N1—C4	109.6 (5)	H7A—C7—H7B	108.2
C5—N1—C4	110.6 (5)	N4—C8—C7	109.3 (6)
C1—N1—H1	109.3	N4—C8—H8A	109.8
C5—N1—H1	109.3	C7—C8—H8A	109.8
C4—N1—H1	109.3	N4—C8—H8B	109.8
C3—N2—C6	110.4 (5)	C7—C8—H8B	109.8
C3—N2—C2	110.4 (5)	H8A—C8—H8B	108.3
C6—N2—C2	110.1 (5)	N3—C9—C10	109.3 (5)
C3—N2—H2	108.6	N3—C9—H9A	109.8
C6—N2—H2	108.6	C10—C9—H9A	109.8
C2—N2—H2	108.6	N3—C9—H9B	109.8
C7—N3—C9	109.1 (5)	C10—C9—H9B	109.8
C7—N3—C11	111.4 (6)	H9A—C9—H9B	108.3
C9—N3—C11	108.9 (6)	N4—C10—C9	108.7 (5)
C7—N3—H3	109.1	N4—C10—H10A	109.9
C9—N3—H3	109.1	C9—C10—H10A	109.9
C11—N3—H3	109.1	N4—C10—H10B	109.9
C10—N4—C12	110.1 (7)	C9—C10—H10B	109.9
C10—N4—C8	111.6 (7)	H10A—C10—H10B	108.3
C12—N4—C8	108.0 (8)	N3—C11—C12	106.5 (7)
C10—N4—H4	109.0	N3—C11—H11A	110.4
C12—N4—H4	109.0	C12—C11—H11A	110.4
C8—N4—H4	109.0	N3—C11—H11B	110.4
N1—C1—C2	110.0 (5)	C12—C11—H11B	110.4
N1—C1—H1A	109.7	H11A—C11—H11B	108.6
C2—C1—H1A	109.7	N4—C12—C11	109.8 (6)
N1—C1—H1B	109.7	N4—C12—H12A	109.7
C2—C1—H1B	109.7	C11—C12—H12A	109.7
H1A—C1—H1B	108.2	N4—C12—H12B	109.7
N2—C2—C1	108.3 (6)	C11—C12—H12B	109.7
N2—C2—H2A	110.0	H12A—C12—H12B	108.2
C1—C2—H2A	110.0	H13A—O—H13B	105 (4)
N2—C2—H2B	110.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl6ii	0.95	2.67	3.391 (6)	134
N2—H2···Cl1iii	0.88	2.78	3.378 (4)	126
N2—H2···Cl3iii	0.88	2.62	3.281 (6)	133
N2—H2···Oiii	0.88	2.46	3.040 (7)	124
N3—H3···Cl8iv	0.89	2.82	3.418 (7)	126
N3—H3···Cl9iv	0.89	2.38	3.132 (9)	143
N4—H4···Cl3i	0.87	2.66	3.303 (6)	131
N4—H4···Oi	0.87	2.30	3.026 (8)	143
O—H13A···Cl5	0.84	2.43	3.185 (7)	151
O—H13B···Cl9iv	0.83	2.66	3.210 (5)	126