trans-Dichloridobis(2,2-dimethyl-prop-ane-1,3-diamine-κN,N')chromium(III) perchlorate.

In the title salt, [CrCl(2)(C(5)H(14)N(2))(2)]ClO(4), the Cr atom is in a trans-CrCl(2)N(4) octa-hedral environment comprising the four N atoms of two chelating 2,2-dimethyl-propane-1,3-diamine ligands and two Cl atoms. The two six-membered CrC(3)N(2) rings in the cation adopt anti chair-chair conformations with respect to each other. The perchlorate anion is disordered over two positions in respect of the Cl and an O atom in a 6:4 ratio. N-H⋯O hydrogen bonds link the cations and anions into a layer structure.

Related literature

For the synthesis, see: House (1986 ▶). For related structures, see: Choi et al. (2002 ▶, 2007 ▶). For the spectroscopic properties, see: Choi (2000 ▶); Poon & Pun (1980 ▶).

Experimental

Crystal data

[CrCl2(C5n class="Species">H14N2)2]ClO4

M = 426.71

Monoclinic,

a = 6.6373 (6) Å

b = 20.767 (2) Å

c = 13.878 (2) Å

β = 100.249 (9)°

V = 1882.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.05 mm−1

T = 298 (2) K

0.32 × 0.30 × 0.25 mm

Data collection

Stoe Stadi-4 diffractometer

Absorption correction: numerical (X-SHAPE; Stoe & Cie, 1996 ▶) T min = 0.805, T max = 0.942

4305 measured reflections

4305 independent reflections

3453 reflections with I > 2σ(I)

3 standard reflections frequency: 60 min intensity decay: 2.7%

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.146

S = 1.11

4305 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.81 e Å−3

Data collection: STADI-4 (Stoe & Cie, 1996 ▶); cell refinement: STADI-4; data reduction: X-RED (Stoe & Cie, 1996 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032911/ng2499sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032911/ng2499Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CrCl2(C5H14N2)2]ClO4	F(000) = 892
Mr = 426.71	Dx = 1.506 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P_2ybc	Cell parameters from 54 reflections
a = 6.6373 (6) Å	θ = 9.5–10.4°
b = 20.767 (2) Å	µ = 1.05 mm−1
c = 13.878 (2) Å	T = 298 K
β = 100.249 (9)°	Block, green
V = 1882.4 (4) Å3	0.32 × 0.30 × 0.25 mm
Z = 4

Stoe Stadi-4 diffractometer	3453 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 27.5°, θmin = 1.8°
ω/2–θ scans	h = −8→8
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 1996)	k = 0→26
Tmin = 0.805, Tmax = 0.942	l = 0→18
4305 measured reflections	3 standard reflections every 60 min
4305 independent reflections	intensity decay: 2.7%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0733P)2 + 1.4729P] where P = (Fo2 + 2Fc2)/3
4305 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.81 e Å−3

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	Occ. (<1)
Cr	0.43254 (6)	0.23278 (2)	0.57694 (3)	0.03056 (15)
Cl1	0.67222 (13)	0.25634 (5)	0.47898 (7)	0.0540 (2)
Cl2	0.18895 (12)	0.21076 (4)	0.67312 (7)	0.0493 (2)
Cl3A	0.9541 (3)	0.11988 (10)	0.31249 (14)	0.0471 (4)	0.60
Cl3B	0.8697 (4)	0.11095 (15)	0.3227 (2)	0.0434 (6)	0.40
O4B	0.6845 (14)	0.1083 (5)	0.3541 (7)	0.096 (3)	0.40
O4A	1.1593 (9)	0.1344 (3)	0.3048 (5)	0.0913 (18)	0.60
O1	0.8766 (6)	0.06609 (19)	0.2505 (3)	0.0957 (12)
O2	0.8510 (7)	0.1748 (2)	0.2793 (3)	0.1124 (15)
O3	0.9840 (9)	0.1052 (3)	0.4093 (3)	0.140 (2)
N1	0.6658 (4)	0.20091 (13)	0.6894 (2)	0.0420 (6)
H1AN	0.7834	0.2010	0.6656	0.050*
H1BN	0.6795	0.2305	0.7375	0.050*
N2	0.4181 (4)	0.13895 (13)	0.5210 (2)	0.0466 (7)
H2AN	0.2998	0.1354	0.4782	0.056*
H2BN	0.5200	0.1348	0.4865	0.056*
N3	0.1983 (4)	0.26418 (12)	0.46576 (19)	0.0385 (6)
H3AN	0.1880	0.2354	0.4167	0.046*
H3BN	0.0806	0.2622	0.4893	0.046*
N4	0.4506 (4)	0.32609 (13)	0.6350 (2)	0.0448 (6)
H4AN	0.3526	0.3297	0.6719	0.054*
H4BN	0.5717	0.3295	0.6758	0.054*
C1	0.6476 (5)	0.13679 (16)	0.7353 (2)	0.0444 (7)
H1A	0.5282	0.1372	0.7667	0.053*
H1B	0.7668	0.1302	0.7860	0.053*
C2	0.6295 (5)	0.07995 (15)	0.6641 (3)	0.0411 (7)
C3	0.6162 (7)	0.01867 (19)	0.7255 (3)	0.0644 (11)
H3A	0.6049	−0.0184	0.6836	0.077*
H3B	0.4982	0.0212	0.7565	0.077*
H3C	0.7374	0.0151	0.7746	0.077*
C4	0.8169 (6)	0.07509 (19)	0.6154 (3)	0.0569 (9)
H4A	0.8011	0.0393	0.5708	0.068*
H4B	0.9368	0.0688	0.6645	0.068*
H4C	0.8311	0.1141	0.5801	0.068*
C5	0.4308 (5)	0.08283 (16)	0.5890 (3)	0.0495 (8)
H5A	0.4181	0.0435	0.5507	0.059*
H5B	0.3161	0.0846	0.6235	0.059*
C6	0.2096 (5)	0.32895 (16)	0.4223 (2)	0.0441 (7)
H6A	0.0874	0.3356	0.3735	0.053*
H6B	0.3261	0.3300	0.3889	0.053*
C7	0.2293 (5)	0.38464 (15)	0.4953 (2)	0.0410 (7)
C8	0.2337 (8)	0.4469 (2)	0.4358 (4)	0.0715 (12)
H8A	0.2455	0.4833	0.4791	0.086*
H8B	0.1095	0.4503	0.3886	0.086*
H8C	0.3488	0.4459	0.4026	0.086*
C9	0.4311 (5)	0.38267 (15)	0.5681 (3)	0.0469 (8)
H9A	0.5435	0.3821	0.5320	0.056*
H9B	0.4433	0.4217	0.6071	0.056*
C10	0.0472 (6)	0.38715 (19)	0.5480 (3)	0.0571 (9)
H10A	0.0640	0.4224	0.5935	0.069*
H10B	0.0388	0.3475	0.5827	0.069*
H10C	−0.0762	0.3932	0.5010	0.069*

	U11	U22	U33	U12	U13	U23
Cr	0.0243 (2)	0.0293 (2)	0.0375 (3)	0.00052 (16)	0.00378 (17)	−0.00218 (18)
Cl1	0.0375 (4)	0.0574 (5)	0.0726 (6)	0.0075 (4)	0.0244 (4)	0.0073 (4)
Cl2	0.0377 (4)	0.0561 (5)	0.0578 (5)	0.0062 (3)	0.0185 (4)	0.0123 (4)
Cl3A	0.0561 (12)	0.0449 (9)	0.0375 (8)	0.0080 (9)	0.0011 (9)	−0.0001 (6)
Cl3B	0.0381 (13)	0.0507 (14)	0.0405 (12)	0.0016 (11)	0.0046 (11)	0.0027 (9)
O4B	0.077 (5)	0.122 (8)	0.096 (6)	−0.025 (5)	0.034 (5)	−0.052 (6)
O4A	0.065 (3)	0.100 (4)	0.099 (4)	−0.011 (3)	−0.013 (3)	0.000 (4)
O1	0.110 (3)	0.091 (3)	0.092 (2)	−0.029 (2)	0.034 (2)	−0.038 (2)
O2	0.126 (3)	0.077 (2)	0.122 (3)	0.025 (2)	−0.010 (3)	0.024 (2)
O3	0.167 (5)	0.178 (5)	0.062 (2)	0.004 (4)	−0.019 (3)	0.017 (3)
N1	0.0319 (12)	0.0373 (13)	0.0526 (16)	0.0014 (10)	−0.0036 (11)	−0.0012 (12)
N2	0.0489 (15)	0.0369 (14)	0.0502 (16)	0.0038 (12)	−0.0017 (12)	−0.0068 (12)
N3	0.0332 (12)	0.0391 (14)	0.0420 (14)	0.0029 (10)	0.0031 (10)	−0.0021 (11)
N4	0.0485 (15)	0.0358 (13)	0.0460 (15)	0.0014 (11)	−0.0029 (12)	−0.0048 (12)
C1	0.0439 (17)	0.0408 (17)	0.0467 (17)	0.0064 (13)	0.0035 (14)	0.0064 (14)
C2	0.0373 (15)	0.0323 (15)	0.0554 (19)	0.0035 (12)	0.0126 (13)	0.0059 (13)
C3	0.070 (3)	0.044 (2)	0.084 (3)	0.0058 (18)	0.024 (2)	0.0195 (19)
C4	0.0474 (19)	0.053 (2)	0.076 (3)	0.0068 (16)	0.0259 (18)	0.0017 (19)
C5	0.0434 (17)	0.0322 (16)	0.071 (2)	−0.0017 (13)	0.0040 (16)	−0.0052 (15)
C6	0.0467 (17)	0.0487 (18)	0.0371 (16)	0.0131 (14)	0.0080 (13)	0.0041 (14)
C7	0.0417 (16)	0.0352 (15)	0.0479 (17)	0.0068 (12)	0.0133 (13)	0.0069 (13)
C8	0.083 (3)	0.045 (2)	0.086 (3)	0.007 (2)	0.015 (2)	0.022 (2)
C9	0.0448 (18)	0.0321 (15)	0.064 (2)	−0.0009 (13)	0.0094 (16)	−0.0003 (14)
C10	0.049 (2)	0.052 (2)	0.077 (3)	0.0090 (16)	0.0259 (19)	−0.0037 (18)

Cr—N3	2.090 (3)	C1—H1A	0.9700
Cr—N2	2.093 (3)	C1—H1B	0.9700
Cr—N4	2.094 (3)	C2—C4	1.522 (4)
Cr—N1	2.100 (3)	C2—C5	1.530 (5)
Cr—Cl2	2.3179 (9)	C2—C3	1.543 (5)
Cr—Cl1	2.3212 (9)	C3—H3A	0.9600
Cl3A—Cl3B	0.629 (2)	C3—H3B	0.9600
Cl3A—O3	1.357 (4)	C3—H3C	0.9600
Cl3A—O2	1.368 (4)	C4—H4A	0.9600
Cl3A—O4A	1.418 (6)	C4—H4B	0.9600
Cl3A—O1	1.447 (4)	C4—H4C	0.9600
Cl3B—O3	1.308 (5)	C5—H5A	0.9700
Cl3B—O1	1.374 (5)	C5—H5B	0.9700
Cl3B—O4B	1.377 (9)	C6—C7	1.528 (5)
Cl3B—O2	1.453 (5)	C6—H6A	0.9700
N1—C1	1.490 (4)	C6—H6B	0.9700
N1—H1AN	0.9000	C7—C10	1.520 (5)
N1—H1BN	0.9000	C7—C9	1.528 (5)
N2—C5	1.492 (4)	C7—C8	1.537 (5)
N2—H2AN	0.9000	C8—H8A	0.9600
N2—H2BN	0.9000	C8—H8B	0.9600
N3—C6	1.481 (4)	C8—H8C	0.9600
N3—H3AN	0.9000	C9—H9A	0.9700
N3—H3BN	0.9000	C9—H9B	0.9700
N4—C9	1.488 (4)	C10—H10A	0.9600
N4—H4AN	0.9000	C10—H10B	0.9600
N4—H4BN	0.9000	C10—H10C	0.9600
C1—C2	1.530 (5)
N3—Cr—N2	92.17 (10)	N1—C1—C2	114.6 (3)
N3—Cr—N4	88.82 (10)	N1—C1—H1A	108.6
N2—Cr—N4	179.01 (11)	C2—C1—H1A	108.6
N3—Cr—N1	179.46 (11)	N1—C1—H1B	108.6
N2—Cr—N1	87.78 (11)	C2—C1—H1B	108.6
N4—Cr—N1	91.24 (11)	H1A—C1—H1B	107.6
N3—Cr—Cl2	89.04 (8)	C4—C2—C5	111.9 (3)
N2—Cr—Cl2	92.25 (9)	C4—C2—C1	111.2 (3)
N4—Cr—Cl2	87.65 (9)	C5—C2—C1	111.7 (3)
N1—Cr—Cl2	90.42 (8)	C4—C2—C3	108.8 (3)
N3—Cr—Cl1	89.95 (8)	C5—C2—C3	106.4 (3)
N2—Cr—Cl1	88.28 (9)	C1—C2—C3	106.6 (3)
N4—Cr—Cl1	91.84 (9)	C2—C3—H3A	109.5
N1—Cr—Cl1	90.59 (8)	C2—C3—H3B	109.5
Cl2—Cr—Cl1	178.87 (4)	H3A—C3—H3B	109.5
O3—Cl3A—O2	119.8 (4)	C2—C3—H3C	109.5
Cl3B—Cl3A—O4A	170.0 (5)	H3A—C3—H3C	109.5
O3—Cl3A—O4A	98.6 (4)	H3B—C3—H3C	109.5
O2—Cl3A—O4A	103.2 (4)	C2—C4—H4A	109.5
O3—Cl3A—O1	112.9 (3)	C2—C4—H4B	109.5
O2—Cl3A—O1	109.9 (3)	H4A—C4—H4B	109.5
O4A—Cl3A—O1	111.3 (3)	C2—C4—H4C	109.5
O3—Cl3A—O4B	70.5 (4)	H4A—C4—H4C	109.5
O2—Cl3A—O4B	77.1 (4)	H4B—C4—H4C	109.5
O4A—Cl3A—O4B	166.7 (4)	N2—C5—C2	114.0 (3)
O1—Cl3A—O4B	80.6 (3)	N2—C5—H5A	108.8
O3—Cl3B—O1	121.3 (4)	C2—C5—H5A	108.8
O3—Cl3B—O4B	96.3 (5)	N2—C5—H5B	108.8
O1—Cl3B—O4B	110.6 (4)	C2—C5—H5B	108.8
O3—Cl3B—O2	117.1 (4)	H5A—C5—H5B	107.7
O1—Cl3B—O2	109.2 (3)	N3—C6—C7	115.0 (3)
O4B—Cl3B—O2	98.8 (6)	N3—C6—H6A	108.5
O3—Cl3B—O4A	74.2 (3)	C7—C6—H6A	108.5
O1—Cl3B—O4A	85.3 (3)	N3—C6—H6B	108.5
O4B—Cl3B—O4A	164.1 (5)	C7—C6—H6B	108.5
O2—Cl3B—O4A	75.2 (3)	H6A—C6—H6B	107.5
C1—N1—Cr	119.62 (19)	C10—C7—C6	111.3 (3)
C1—N1—H1AN	107.4	C10—C7—C9	111.2 (3)
Cr—N1—H1AN	107.4	C6—C7—C9	112.3 (3)
C1—N1—H1BN	107.4	C10—C7—C8	108.8 (3)
Cr—N1—H1BN	107.4	C6—C7—C8	106.7 (3)
H1AN—N1—H1BN	106.9	C9—C7—C8	106.2 (3)
C5—N2—Cr	119.9 (2)	C7—C8—H8A	109.5
C5—N2—H2AN	107.3	C7—C8—H8B	109.5
Cr—N2—H2AN	107.3	H8A—C8—H8B	109.5
C5—N2—H2BN	107.3	C7—C8—H8C	109.5
Cr—N2—H2BN	107.3	H8A—C8—H8C	109.5
H2AN—N2—H2BN	106.9	H8B—C8—H8C	109.5
C6—N3—Cr	119.9 (2)	N4—C9—C7	113.7 (3)
C6—N3—H3AN	107.3	N4—C9—H9A	108.8
Cr—N3—H3AN	107.3	C7—C9—H9A	108.8
C6—N3—H3BN	107.3	N4—C9—H9B	108.8
Cr—N3—H3BN	107.3	C7—C9—H9B	108.8
H3AN—N3—H3BN	106.9	H9A—C9—H9B	107.7
C9—N4—Cr	119.9 (2)	C7—C10—H10A	109.5
C9—N4—H4AN	107.4	C7—C10—H10B	109.5
Cr—N4—H4AN	107.4	H10A—C10—H10B	109.5
C9—N4—H4BN	107.4	C7—C10—H10C	109.5
Cr—N4—H4BN	107.4	H10A—C10—H10C	109.5
H4AN—N4—H4BN	106.9	H10B—C10—H10C	109.5
O2—Cl3A—Cl3B—O3	−123.6 (4)	O1—Cl3A—O2—Cl3B	67.3 (4)
O4A—Cl3A—Cl3B—O3	20 (3)	O4B—Cl3A—O2—Cl3B	−7.5 (5)
O1—Cl3A—Cl3B—O3	123.2 (4)	O3—Cl3B—O2—Cl3A	67.5 (5)
O4B—Cl3A—Cl3B—O3	−80 (3)	O1—Cl3B—O2—Cl3A	−75.3 (4)
O3—Cl3A—Cl3B—O1	−123.2 (4)	O4B—Cl3B—O2—Cl3A	169.2 (6)
O2—Cl3A—Cl3B—O1	113.2 (3)	O4A—Cl3B—O2—Cl3A	4.3 (4)
O4A—Cl3A—Cl3B—O1	−103 (3)	O1—Cl3B—O3—Cl3A	76.7 (5)
O4B—Cl3A—Cl3B—O1	157 (3)	O4B—Cl3B—O3—Cl3A	−164.5 (7)
O3—Cl3A—Cl3B—O4B	80 (3)	O2—Cl3B—O3—Cl3A	−61.3 (5)
O2—Cl3A—Cl3B—O4B	−43 (3)	O4A—Cl3B—O3—Cl3A	2.4 (4)
O4A—Cl3A—Cl3B—O4B	100 (4)	O2—Cl3A—O3—Cl3B	72.8 (5)
O1—Cl3A—Cl3B—O4B	−157 (3)	O4A—Cl3A—O3—Cl3B	−176.6 (6)
O3—Cl3A—Cl3B—O2	123.6 (4)	O1—Cl3A—O3—Cl3B	−59.0 (5)
O4A—Cl3A—Cl3B—O2	143 (3)	O4B—Cl3A—O3—Cl3B	11.2 (5)
O1—Cl3A—Cl3B—O2	−113.2 (3)	N2—Cr—N1—C1	−41.0 (2)
O4B—Cl3A—Cl3B—O2	43 (3)	N4—Cr—N1—C1	138.9 (2)
O3—Cl3A—Cl3B—O4A	−20 (3)	Cl2—Cr—N1—C1	51.3 (2)
O2—Cl3A—Cl3B—O4A	−143 (3)	Cl1—Cr—N1—C1	−129.2 (2)
O1—Cl3A—Cl3B—O4A	103 (3)	N3—Cr—N2—C5	−137.9 (2)
O4B—Cl3A—Cl3B—O4A	−100 (4)	N1—Cr—N2—C5	41.6 (2)
O3—Cl3B—O4B—Cl3A	78 (3)	Cl2—Cr—N2—C5	−48.8 (2)
O1—Cl3B—O4B—Cl3A	−155 (3)	Cl1—Cr—N2—C5	132.2 (2)
O2—Cl3B—O4B—Cl3A	−41 (2)	N2—Cr—N3—C6	−141.5 (2)
O4A—Cl3B—O4B—Cl3A	25.7 (16)	N4—Cr—N3—C6	38.6 (2)
O3—Cl3A—O4B—Cl3B	−96 (3)	Cl2—Cr—N3—C6	126.3 (2)
O2—Cl3A—O4B—Cl3B	135 (3)	Cl1—Cr—N3—C6	−53.2 (2)
O4A—Cl3A—O4B—Cl3B	−132 (3)	N3—Cr—N4—C9	−39.7 (2)
O1—Cl3A—O4B—Cl3B	22 (2)	N1—Cr—N4—C9	140.8 (2)
O3—Cl3A—O4A—Cl3B	19 (3)	Cl2—Cr—N4—C9	−128.8 (2)
O2—Cl3A—O4A—Cl3B	142 (3)	Cl1—Cr—N4—C9	50.2 (2)
O1—Cl3A—O4A—Cl3B	−100 (3)	Cr—N1—C1—C2	59.1 (3)
O4B—Cl3A—O4A—Cl3B	53 (3)	N1—C1—C2—C4	60.6 (4)
O3—Cl3B—O4A—Cl3A	−160 (3)	N1—C1—C2—C5	−65.2 (4)
O1—Cl3B—O4A—Cl3A	76 (3)	N1—C1—C2—C3	179.0 (3)
O4B—Cl3B—O4A—Cl3A	−105 (4)	Cr—N2—C5—C2	−60.0 (4)
O2—Cl3B—O4A—Cl3A	−35 (3)	C4—C2—C5—N2	−60.1 (4)
O3—Cl3B—O1—Cl3A	−75.2 (5)	C1—C2—C5—N2	65.2 (4)
O4B—Cl3B—O1—Cl3A	173.4 (8)	C3—C2—C5—N2	−178.8 (3)
O2—Cl3B—O1—Cl3A	65.8 (4)	Cr—N3—C6—C7	−56.9 (3)
O4A—Cl3B—O1—Cl3A	−6.8 (4)	N3—C6—C7—C10	−60.2 (4)
O3—Cl3A—O1—Cl3B	59.8 (5)	N3—C6—C7—C9	65.2 (4)
O2—Cl3A—O1—Cl3B	−76.8 (5)	N3—C6—C7—C8	−178.8 (3)
O4A—Cl3A—O1—Cl3B	169.6 (6)	Cr—N4—C9—C7	58.7 (3)
O4B—Cl3A—O1—Cl3B	−4.3 (5)	C10—C7—C9—N4	59.8 (4)
O3—Cl3A—O2—Cl3B	−65.8 (5)	C6—C7—C9—N4	−65.7 (4)
O4A—Cl3A—O2—Cl3B	−173.9 (6)	C8—C7—C9—N4	178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1BN···O2i	0.90	2.29	3.030 (5)	139
N2—H2AN···O3ii	0.90	2.23	3.099 (6)	162
N2—H2AN···O4Aii	0.90	2.42	3.183 (6)	143
N2—H2BN···O4B	0.90	2.36	3.217 (9)	159
N3—H3AN···O4Aii	0.90	2.60	3.482 (7)	168
N4—H4BN···O2i	0.90	2.14	3.030 (5)	172
N4—H4AN···O4Aiii	0.90	2.54	3.403 (8)	161
N1—H1AN···Cl2iv	0.90	2.68	3.525 (3)	156
N3—H3BN···Cl1ii	0.90	2.69	3.533 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1BN⋯O2i	0.90	2.29	3.030 (5)	139
N2—H2AN⋯O3ii	0.90	2.23	3.099 (6)	162
N2—H2AN⋯O4Aii	0.90	2.42	3.183 (6)	143
N2—H2BN⋯O4B	0.90	2.36	3.217 (9)	159
N3—H3AN⋯O4Aii	0.90	2.60	3.482 (7)	168
N4—H4BN⋯O2i	0.90	2.14	3.030 (5)	172
N4—H4AN⋯O4Aiii	0.90	2.54	3.403 (8)	161

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