Crystal structure of trans-bis-(ethane-1,2-diamine-κ(2) N,N')bis-(thio-cyanato-κN)chromium(III) perchlorate from synchrotron data.

The structure of the title compound, [Cr(NCS)2(C2H8N2)2]ClO4, has been determined from synchroton data. The asymmetric unit consists of one half of a centrosymmetric Cr(III) complex cation and half of a perchlorate anion with the Cl atom on a twofold rotation axis. The Cr(III) ion is coordinated by the four N atoms of two ethane-1,2-di-amine (en) ligands in the equatorial plane and two N-bound thio-cyanate (NCS(-)) anions in a trans-axial arrangement, displaying a slightly distorted octa-hedral geometry with crystallographic inversion symmetry. The Cr-N(en) bond lengths are in the range 2.053 (16)-2.09 (2) Å, while the Cr-N(thio-cyanate) bond length is 1.983 (2) Å. The five-membered en rings are disordered over two sites, with occupancy ratios of 0.522 (16):0.478 (16). Each ClO4 (-) anion is disordered over two sites with equal occupancy. The crystal structure is stabilized by inter-molecular hydrogen bonds involving the en NH2 groups as donors and perchlorate O and thio-cyanate S atoms as acceptors.

Chemical context

Considerable attention has ben class="Chemical">en focussed for some time on metal complexes containing thio­cyanate ligands because of their ability to coordinate through either the N or S atoms. Ethane-1,2-di­amine (en) can coordinate to a central metal ion as a bidentate ligand via the two N atoms, forming a five-membered chelate ring. The [Cr(NCS)2(en)2]+ cation can form either trans or cis geometric isomers. Trans and cis isomers of the complex cation with SCN− or ClO4 − counter-anions have been prepared and their IR spectral properties reported (House, 1973 ▸; Sandrini et al., 1978 ▸; De et al., 1987 ▸). IR and electronic spectral properties are useful in determining the geometric isomers of chromium(III) complexes with mixed ligands (Choi, 2000 ▸; Choi et al., 2004 ▸; Choi & Moon, 2014 ▸). However, it should be noted that the geometric assignments based on spectroscopic studies are not always definitive.

In a recent publication, we desn class="Chemical">cribed the synthesis and crystal structure of trans-[Cr(NCS)2(en)2]2[ZnCl4] (Moon & Choi, 2015 ▸). The asymmetric unit of this complex contained four halves of centrosymmetric [Cr(NCS)2(en)2]+ complex cations and one [ZnCl4]2− anion. To compare and contrast this structure with a complex of this cation with a different counter-anion we report here the structure of trans-[Cr(NCS)2(en)2]ClO4, (I).

Structural commentary

Fig. 1 ▸ shows an ellipsoid plot of trans-[Cr(NCS)2(en)2]ClO4, (I), with the atom-numbering scheme. In the structure of (I), there is a cn class="Chemical">entrosymmetric CrIII complex cation with two en ligands bound through their N atoms in equatorial sites and the two axial N-bound thio­cyanate anions in a trans configuration. The asymmetric unit is composed of half of one complex cation and half a ClO4 − anion. The CrIII atom is located on a crystallographic centre of symmetry, so this complex cation has mol­ecular C symmetry, while the the Cl atom of the perchlorate anion lies on a twofold rotation axis. The bidentate en ligand adopts a stable gauche conformation similar to that observed in related compounds (Brenčič & Leban, 1981 ▸; Choi et al., 2010 ▸). The Cr—N bond lengths for the en ligand range from 2.053 (16) to 2.09 (2) Å, and these bond lengths are in good agreement with those observed in trans-[CrF2(en)2]ClO4 (Brenčič & Leban, 1981 ▸), trans-[CrBr2(en)2]ClO4 (Choi et al., 2010 ▸), trans-[CrCl2(Me2tn)2]2ZnCl4 (Me2tn = 2,2-di­methyl­propane-1,3-di­amine; Choi et al., 2011 ▸) and trans-[CrF2(2,2,3-tet)]ClO4 (2,2,3-tet = 1,4,7,11-tetra­aza­undecane; Choi & Moon, 2014 ▸). The Cr—N(thio­cyanate) bond length is 1.983 (2) Å and is similar to the average values of 1.985 (2), 1.995 (6), 1.983 (2) and 1.996 (15) Å found in trans-[Cr(NCS)2(en)2]2ZnCl4 (Moon & Choi, 2015 ▸), trans-[Cr(NCS)2(cyclam)]2ZnCl4 (cyclam = 1,4,8,11-tetra­aza­cyclo­tetra­decane (Moon et al., 2015 ▸), trans-[Cr(NCS)2(Me2tn)2]NCS (Choi & Lee, 2009 ▸) and cis-[Cr(NCS)2(cyclam)]NCS (Moon et al., 2013 ▸), respectively. The N-coordinated iso­thio­cyanate group is almost linear, with an N—C—S angle of 179.3 (3)°. The ClO4 − counter-anion lies well outside the coordination sphere of the complex and, because of significant disorder, the tetra­hedral geometry of this anion is severely distorted.

Figure 1

The mol­ecular structure of (I), drawn with 20% probability displacement ellipsoids. Atoms of the minor disorder components have been omitted for clarity.

Supra­molecular features

In the crystal, an n class="Chemical">N—H⋯S hydrogen bond links neighbouring cations, while a series of N—H⋯O contacts link the cations to neighbouring anions (Table 1 ▸). An extensive array of these contacts generate a three-dimensional network of mol­ecules stacked along the b-axis direction (Fig. 2 ▸). These hydrogen-bonded networks help to stabilize the crystal structure.

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N2AH2A1S1i	0.89	2.45	3.324(17)	167
N2AH2A2O2B ii	0.89	2.41	3.187(19)	146
N3AH3A1O1B iii	0.89	2.58	3.282(16)	136
N2BH2B1S1i	0.89	2.77	3.459(17)	135
N3BH3B1O2C iii	0.89	2.45	3.22(2)	145
N3BH3B2S1iv	0.89	2.38	3.255(18)	166

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

Figure 2

The crystal packing of (I), viewed perpendicular to the ac plane. Dashed lines represent N—H⋯O (red) and N—H⋯S (blue) hydrogen-bonding inter­actions, respectively. The minor disorder components and C-bound H atoms have been omitted for clarity.

Database survey

A search of the Cambridge Structural Database (Version 5.36, last update February 2015; Groom & Allen, 2014 ▸) indicates a total of 13 hits for n class="Chemical">CrIII complexes with a [CrL 2(en)2]+ unit. The crystal structures of trans-[CrCl2(en)2]Cl·HCl·2H2O (Ooi et al., 1960 ▸), trans-[CrF2(en)2]X (X = ClO4, Cl, Br) (Brenčič & Leban, 1981 ▸), cis-[CrF2(en)2]ClO4 (Brenčič et al., 1987 ▸), trans-[CrBr2(en)2]ClO4 (Choi et al., 2010 ▸) have been reported previously. Recently, we have also reported the closely related crystal structure of [Cr(NCS)2(en)2]2[ZnCl4], in which there are four crystallographically independent CrIII complex cations that also adopt a trans configuration. However, a crystal structure of [Cr(NCS)2(en)2]+ with a ClO4 anion has not been reported previously.

Synthesis and crystallization

All chemicals were reagent grade materials and were used without further purification. The title compound, n class="Chemical">trans-[Cr(NCS)2(en)2]ClO4 was prepared according to the literature method (Sandrini et al., 1978 ▸). The crude perchlorate salt (0.33 g) was dissolved in 20 mL of 0.1 M HCl at 333 K. The filtrate was added to 6 mL of 60% HClO4. The resulting solution was allowed to stand at room temperature for 2 d to give orange block-like crystals suitable for X-ray structural analysis. IR spectrum (KBr, cm−1) : 3247 (vs), 3208 (vs), 3131 (vs) and 3097 (vs) (ν NH), 2966 (s), 2955 (s) and 2893 (s) (ν CH), 2077 (vs) (ν CN), 1586 (vs) (δ NH2), 1459 (s) (δ CH2), 1365 (m) (ν CN), 1326 (s) (ω NH2), 1290 (vs) (ω CH2), 1146 (vs) (γ NH2), 1117 (vs) (ν CN), 1088 (vs) (ν Cl—O), 1047 (vs) (γ CH2), 1007 (s), 983 (s), 873 (m) (ρ CH2), 849 (w) (ρ NH2), 729 (vs), 636 (s) and 626 (vs) (δ OClO), 558 (vs), 559 (s) (δ CCC), 501 (vs), 478 (s) (δ NCS), 444 (m) and 419 (m) (ν Cr—N).

Refinement

Crystal data, data collection and structure refinemn class="Chemical">ent details are summarized in Table 2 ▸. In the title compound, the ethane-1,2-di­amine group is disordered with atoms N2A/N2B, C2A/C2B, C3A/C3B and N3A/N3B positionally disordered over two sets of sites with a refined occupancy ratio of 0.522 (16):0.478 (16). The half mol­ecules of each distorted perchlorate anion are disordered over two sites of equal occupancy, with atoms Cl1B/Cl1C and O2B/O1C refined using EXYZ/EADP constraints. All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.97 Å and N—H = 0.89 Å, and with U iso(H) values of 1.2 of the parent atoms.

Table 2

Experimental details

Crystal data
Chemical formula	[Cr(NCS)2(C2H8N2)2]ClO4
M r	387.82
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	260
a, b, c ()	15.599(3), 7.4440(15), 13.792(3)
()	105.83(3)
V (3)	1540.8(6)
Z	4
Radiation type	Synchrotron, = 0.630
(mm1)	0.86
Crystal size (mm)	0.14 0.13 0.13
Data collection
Diffractometer	ADSC Q210 CCD area detector
Absorption correction	Empirical (using intensity measurements) (HKL3000sm SCALEAPCK; Otwinowski Minor, 1997 ▸)
T min, T max	0.893, 0.897
No. of measured, independent and observed [I > 2(I)] reflections	8172, 2121, 2019
R int	0.015
(sin /)max (1)	0.696
Refinement
R[F 2 > 2(F 2)], wR(F 2), S	0.060, 0.178, 1.09
No. of reflections	2121
No. of parameters	140
H-atom treatment	H-atom parameters constrained
max, min (e 3)	0.74, 1.12

Computer programs: PAL ADSC Quantum-210 ADX Program (Arvai Nielsen, 1983 ▸), HKL3000sm (Otwinowski Minor, 1997 ▸), SHELXT2014/5 (Sheldrick, 2015a ▸), SHELXL2014/7 (Sheldrick, 2015b ▸), DIAMOND (Putz Brandenburg, 2014 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015009184/sj5459sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015009184/sj5459Isup2.hkl

CCDC reference: 1400767

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

[Cr(NCS)2(C2H8N2)2]ClO4	F(000) = 796
Mr = 387.82	Dx = 1.672 Mg m−3
Monoclinic, C2/c	Synchrotron radiation, λ = 0.630 Å
a = 15.599 (3) Å	Cell parameters from 46962 reflections
b = 7.4440 (15) Å	θ = 0.4–33.6°
c = 13.792 (3) Å	µ = 0.86 mm−1
β = 105.83 (3)°	T = 260 K
V = 1540.8 (6) Å3	Block, orange
Z = 4	0.14 × 0.13 × 0.13 mm

ADSC Q210 CCD area-detector diffractometer	2019 reflections with I > 2σ(I)
Radiation source: PLSII 2D bending magnet	Rint = 0.015
ω scan	θmax = 26.0°, θmin = 2.7°
Absorption correction: empirical (using intensity measurements) (HKL3000sm SCALEAPCK; Otwinowski & Minor, 1997)	h = −21→21
Tmin = 0.893, Tmax = 0.897	k = −10→10
8172 measured reflections	l = −19→19
2121 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.060	w = 1/[σ2(Fo2) + (0.1146P)2 + 2.4721P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.178	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.74 e Å−3
2121 reflections	Δρmin = −1.12 e Å−3
140 parameters	Extinction correction: SHELXL2014/7 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.045 (12)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cr1	0.2500	0.2500	0.5000	0.0273 (3)
S1	0.21080 (8)	0.77661 (11)	0.67477 (8)	0.0586 (3)
N1	0.24831 (15)	0.4775 (3)	0.57426 (17)	0.0433 (5)
C1	0.23290 (16)	0.6026 (3)	0.61573 (17)	0.0363 (5)
N2A	0.3423 (12)	0.1308 (19)	0.6213 (13)	0.036 (2)	0.522 (16)
H2A1	0.3272	0.1503	0.6781	0.043*	0.522 (16)
H2A2	0.3442	0.0127	0.6118	0.043*	0.522 (16)
N3A	0.3624 (11)	0.337 (2)	0.4641 (10)	0.043 (3)	0.522 (16)
H3A1	0.3553	0.3266	0.3981	0.052*	0.522 (16)
H3A2	0.3722	0.4525	0.4807	0.052*	0.522 (16)
C2A	0.4311 (5)	0.2126 (10)	0.6277 (8)	0.057 (2)	0.522 (16)
H2A3	0.4784	0.1375	0.6678	0.068*	0.522 (16)
H2A4	0.4355	0.3305	0.6587	0.068*	0.522 (16)
C3A	0.4385 (5)	0.2274 (14)	0.5199 (10)	0.066 (3)	0.522 (16)
H3A3	0.4943	0.2842	0.5191	0.079*	0.522 (16)
H3A4	0.4362	0.1092	0.4897	0.079*	0.522 (16)
N2B	0.3570 (13)	0.164 (2)	0.6143 (14)	0.041 (3)	0.478 (16)
H2B1	0.3654	0.2382	0.6667	0.049*	0.478 (16)
H2B2	0.3464	0.0548	0.6342	0.049*	0.478 (16)
N3B	0.3502 (13)	0.341 (3)	0.4378 (9)	0.040 (2)	0.478 (16)
H3B1	0.3527	0.2732	0.3856	0.048*	0.478 (16)
H3B2	0.3396	0.4543	0.4167	0.048*	0.478 (16)
C2B	0.4369 (4)	0.1614 (15)	0.5773 (8)	0.056 (2)	0.478 (16)
H2B3	0.4355	0.0582	0.5339	0.067*	0.478 (16)
H2B4	0.4902	0.1541	0.6334	0.067*	0.478 (16)
C3B	0.4370 (5)	0.3297 (19)	0.5203 (7)	0.060 (3)	0.478 (16)
H3B3	0.4869	0.3303	0.4911	0.072*	0.478 (16)
H3B4	0.4427	0.4322	0.5651	0.072*	0.478 (16)
Cl1B	0.5000	0.7072 (3)	0.7500	0.0989 (7)	0.5
O1B	0.4393 (4)	0.5672 (9)	0.7711 (5)	0.0762 (16)	0.5
O2B	0.4350 (6)	0.7462 (8)	0.6376 (6)	0.159 (3)	0.5
Cl1C	0.5000	0.7072 (3)	0.7500	0.0989 (7)	0.5
O1C	0.4350 (6)	0.7462 (8)	0.6376 (6)	0.159 (3)	0.5
O2C	0.4488 (11)	0.8416 (15)	0.7860 (8)	0.152 (5)	0.5

	U11	U22	U33	U12	U13	U23
Cr1	0.0366 (4)	0.0229 (3)	0.0251 (3)	0.00353 (14)	0.0128 (2)	−0.00135 (14)
S1	0.0988 (7)	0.0298 (4)	0.0630 (6)	0.0072 (3)	0.0492 (5)	−0.0070 (3)
N1	0.0553 (12)	0.0327 (11)	0.0427 (10)	0.0052 (9)	0.0145 (9)	−0.0097 (8)
C1	0.0472 (12)	0.0289 (10)	0.0356 (10)	0.0012 (9)	0.0163 (9)	−0.0012 (8)
N2A	0.050 (5)	0.024 (3)	0.034 (3)	−0.001 (2)	0.011 (3)	0.004 (2)
N3A	0.047 (5)	0.036 (3)	0.056 (7)	0.006 (3)	0.028 (5)	0.017 (5)
C2A	0.048 (3)	0.044 (3)	0.065 (5)	−0.003 (2)	−0.006 (3)	−0.001 (3)
C3A	0.038 (3)	0.044 (4)	0.121 (8)	0.008 (3)	0.031 (4)	0.026 (5)
N2B	0.048 (6)	0.044 (8)	0.031 (3)	0.012 (5)	0.014 (3)	0.005 (4)
N3B	0.050 (5)	0.043 (4)	0.031 (4)	0.005 (3)	0.019 (4)	0.002 (3)
C2B	0.041 (3)	0.073 (5)	0.051 (5)	0.017 (3)	0.007 (3)	0.003 (4)
C3B	0.045 (3)	0.068 (7)	0.070 (4)	−0.014 (4)	0.023 (3)	−0.013 (4)
Cl1B	0.1112 (15)	0.0671 (10)	0.1316 (18)	0.000	0.0553 (13)	0.000
O1B	0.074 (3)	0.073 (4)	0.083 (4)	−0.009 (3)	0.024 (3)	0.029 (3)
O2B	0.152 (6)	0.199 (8)	0.130 (5)	0.028 (4)	0.045 (5)	0.035 (4)
Cl1C	0.1112 (15)	0.0671 (10)	0.1316 (18)	0.000	0.0553 (13)	0.000
O1C	0.152 (6)	0.199 (8)	0.130 (5)	0.028 (4)	0.045 (5)	0.035 (4)
O2C	0.255 (15)	0.095 (7)	0.121 (8)	−0.038 (9)	0.076 (9)	−0.014 (6)

Cr1—N1	1.983 (2)	C3A—H3A3	0.9700
Cr1—N1i	1.983 (2)	C3A—H3A4	0.9700
Cr1—N3Ai	2.053 (16)	N2B—C2B	1.471 (18)
Cr1—N3A	2.053 (16)	N2B—H2B1	0.8900
Cr1—N2B	2.06 (2)	N2B—H2B2	0.8900
Cr1—N2Bi	2.06 (2)	N3B—C3B	1.514 (17)
Cr1—N2Ai	2.085 (19)	N3B—H3B1	0.8900
Cr1—N2A	2.085 (19)	N3B—H3B2	0.8900
Cr1—N3Bi	2.09 (2)	C2B—C3B	1.479 (17)
Cr1—N3B	2.09 (2)	C2B—H2B3	0.9700
S1—C1	1.617 (3)	C2B—H2B4	0.9700
N1—C1	1.152 (3)	C3B—H3B3	0.9700
N2A—C2A	1.493 (15)	C3B—H3B4	0.9700
N2A—H2A1	0.8900	Cl1B—O1Bii	1.489 (6)
N2A—H2A2	0.8900	Cl1B—O1B	1.489 (6)
N3A—C3A	1.475 (16)	Cl1B—O2Bii	1.630 (8)
N3A—H3A1	0.8900	Cl1B—O2B	1.630 (8)
N3A—H3A2	0.8900	Cl1C—O2Cii	1.450 (13)
C2A—C3A	1.527 (17)	Cl1C—O2C	1.450 (13)
C2A—H2A3	0.9700	Cl1C—O1Cii	1.630 (8)
C2A—H2A4	0.9700	Cl1C—O1C	1.630 (8)
N1—Cr1—N1i	180.0	N2A—C2A—H2A4	110.4
N1—Cr1—N3Ai	90.8 (5)	C3A—C2A—H2A4	110.4
N1i—Cr1—N3Ai	89.2 (5)	H2A3—C2A—H2A4	108.6
N1—Cr1—N3A	89.2 (5)	N3A—C3A—C2A	106.5 (10)
N1i—Cr1—N3A	90.8 (5)	N3A—C3A—H3A3	110.4
N3Ai—Cr1—N3A	180.0	C2A—C3A—H3A3	110.4
N1—Cr1—N2B	89.5 (5)	N3A—C3A—H3A4	110.4
N1i—Cr1—N2B	90.5 (5)	C2A—C3A—H3A4	110.4
N1—Cr1—N2Bi	90.5 (5)	H3A3—C3A—H3A4	108.6
N1i—Cr1—N2Bi	89.5 (5)	C2B—N2B—Cr1	109.0 (9)
N2B—Cr1—N2Bi	180.0 (9)	C2B—N2B—H2B1	109.9
N1—Cr1—N2Ai	87.0 (4)	Cr1—N2B—H2B1	109.9
N1i—Cr1—N2Ai	93.0 (5)	C2B—N2B—H2B2	109.9
N3Ai—Cr1—N2Ai	83.1 (5)	Cr1—N2B—H2B2	109.9
N3A—Cr1—N2Ai	96.9 (5)	H2B1—N2B—H2B2	108.3
N1—Cr1—N2A	93.0 (4)	C3B—N3B—Cr1	106.7 (8)
N1i—Cr1—N2A	87.0 (4)	C3B—N3B—H3B1	110.4
N3Ai—Cr1—N2A	96.9 (5)	Cr1—N3B—H3B1	110.4
N3A—Cr1—N2A	83.1 (5)	C3B—N3B—H3B2	110.4
N2Ai—Cr1—N2A	180.0	Cr1—N3B—H3B2	110.4
N1—Cr1—N3Bi	87.1 (5)	H3B1—N3B—H3B2	108.6
N1i—Cr1—N3Bi	92.9 (5)	N2B—C2B—C3B	107.1 (10)
N2B—Cr1—N3Bi	97.2 (5)	N2B—C2B—H2B3	110.3
N2Bi—Cr1—N3Bi	82.8 (5)	C3B—C2B—H2B3	110.3
N1—Cr1—N3B	92.9 (5)	N2B—C2B—H2B4	110.3
N1i—Cr1—N3B	87.1 (5)	C3B—C2B—H2B4	110.3
N2B—Cr1—N3B	82.8 (5)	H2B3—C2B—H2B4	108.5
N2Bi—Cr1—N3B	97.2 (5)	C2B—C3B—N3B	108.6 (10)
N3Bi—Cr1—N3B	180.0	C2B—C3B—H3B3	110.0
C1—N1—Cr1	168.7 (2)	N3B—C3B—H3B3	110.0
N1—C1—S1	179.3 (3)	C2B—C3B—H3B4	110.0
C2A—N2A—Cr1	107.5 (7)	N3B—C3B—H3B4	110.0
C2A—N2A—H2A1	110.2	H3B3—C3B—H3B4	108.4
Cr1—N2A—H2A1	110.2	O1Bii—Cl1B—O1B	91.2 (5)
C2A—N2A—H2A2	110.2	O1Bii—Cl1B—O2Bii	92.7 (4)
Cr1—N2A—H2A2	110.2	O1B—Cl1B—O2Bii	101.7 (3)
H2A1—N2A—H2A2	108.5	O1Bii—Cl1B—O2B	101.7 (3)
C3A—N3A—Cr1	108.5 (8)	O1B—Cl1B—O2B	92.7 (4)
C3A—N3A—H3A1	110.0	O2Bii—Cl1B—O2B	159.4 (5)
Cr1—N3A—H3A1	110.0	O2Cii—Cl1C—O2C	92.7 (9)
C3A—N3A—H3A2	110.0	O2Cii—Cl1C—O1Cii	86.8 (6)
Cr1—N3A—H3A2	110.0	O2C—Cl1C—O1Cii	79.0 (6)
H3A1—N3A—H3A2	108.4	O2Cii—Cl1C—O1C	79.0 (6)
N2A—C2A—C3A	106.7 (9)	O2C—Cl1C—O1C	86.8 (6)
N2A—C2A—H2A3	110.4	O1Cii—Cl1C—O1C	159.4 (5)
C3A—C2A—H2A3	110.4
Cr1—N2A—C2A—C3A	−42.0 (11)	Cr1—N2B—C2B—C3B	44.2 (13)
Cr1—N3A—C3A—C2A	−44.8 (13)	N2B—C2B—C3B—N3B	−56.3 (15)
N2A—C2A—C3A—N3A	57.9 (14)	Cr1—N3B—C3B—C2B	40.2 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A1···S1iii	0.89	2.45	3.324 (17)	167
N2A—H2A2···O2Biv	0.89	2.41	3.187 (19)	146
N3A—H3A1···O1Bv	0.89	2.58	3.282 (16)	136
N2B—H2B1···S1iii	0.89	2.77	3.459 (17)	135
N3B—H3B1···O2Cv	0.89	2.45	3.22 (2)	145
N3B—H3B2···S1vi	0.89	2.38	3.255 (18)	166