Tris[4-(dimethyl-amino)-pyridinium][(bis-μ-dichlorido)-deca-aqua-dichlorido-dineodymium(III)] penta-chloride dihydrate.

The title compound, (C(7)H(11)N(2))(3)[Nd(2)Cl(4)(H(2)O)(10)]Cl(5)·2H(2)O, consists of three 4-(dimethyl-amino)-pyridinium cations, one of which is disordered about an inversion center, one [Nd(2)Cl(4)(H(2)O)(10)](2+) dication possessing inversion symmetry, five chloride anions, one of which is disordered over two inversion centers, and two lattice water mol-ecules. The 4-(dimethyl-amino)-pyridinium cations are protonated at the pyridine N atoms and form N-H⋯Cl hydrogen bonds with Cl(-) counter-ions. The dimethyl-amino groups (C/N/C) lie close to the plane of the pyridinium rings, making dihedral angles of 1.6 (6)° and 6.5 (3)°. In the crystal, the [Nd(2)Cl(4)(H(2)O)(10)](2+) dications are linked via O-H⋯O and O-H⋯Cl hydrogen bonds, forming sheets lying parallel to the bc plane. These sheets are linked via O-H⋯Cl hydrogen bonds, forming a three-dimensional network. The 4-(dimethyl-amino)-pyridinium cations are located in the cavities and linked to the framework by C-H⋯Cl interactions.

Related literature

For the crystal structures of complexes involving 4-(dimethyl­amino)­pyridinium, see: Chao et al. (1977 ▶); Mayr-Stein & Bolte (2000 ▶); Lo & Ng (2008 ▶, 2009 ▶); Koon et al. (2009 ▶); Benslimane et al. (2012 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

(C7H11N2)3[Nd2Cl4(H2O)10]Cl5·2H2O

M = 1193.26

Triclinic,

a = 9.5172 (4) Å

b = 10.7739 (5) Å

c = 11.9976 (5) Å

α = 74.855 (4)°

β = 69.780 (4)°

γ = 85.075 (4)°

V = 1114.28 (8) Å3

Z = 1

Mo Kα radiation

μ = 2.90 mm−1

T = 180 K

0.36 × 0.22 × 0.16 mm

Data collection

Agilent Xcalibur Sapphire1 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.475, T max = 0.633

23060 measured reflections

4551 independent reflections

4088 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.068

S = 1.11

4551 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.95 e Å−3

Δρmin = −1.76 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812041724/su2506sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041724/su2506Isup2.hkl

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

(C7H11N2)3[Nd2Cl4(H2O)10]Cl5·2H2O	Z = 1
Mr = 1193.26	F(000) = 594
Triclinic, P1	Dx = 1.778 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5172 (4) Å	Cell parameters from 15563 reflections
b = 10.7739 (5) Å	θ = 3.0–28.5°
c = 11.9976 (5) Å	µ = 2.90 mm−1
α = 74.855 (4)°	T = 180 K
β = 69.780 (4)°	Platelet, colourless
γ = 85.075 (4)°	0.36 × 0.22 × 0.16 mm
V = 1114.28 (8) Å3

Agilent Xcalibur Sapphire1 diffractometer	4551 independent reflections
Radiation source: fine-focus sealed tube	4088 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 8.2632 pixels mm-1	θmax = 26.4°, θmin = 3.0°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→13
Tmin = 0.475, Tmax = 0.633	l = −14→14
23060 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0222P)2 + 2.5244P] where P = (Fo2 + 2Fc2)/3
4551 reflections	(Δ/σ)max < 0.001
210 parameters	Δρmax = 0.95 e Å−3
0 restraints	Δρmin = −1.76 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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)
Nd1	0.48488 (2)	0.51184 (2)	0.18894 (2)	0.0276 (1)
Cl1	0.49345 (10)	0.66402 (8)	−0.04455 (7)	0.0285 (3)
Cl11	0.79337 (11)	0.51474 (10)	0.06963 (10)	0.0421 (3)
O11	0.2356 (3)	0.4935 (3)	0.1820 (3)	0.0523 (10)
O12	0.4711 (4)	0.7381 (3)	0.1875 (3)	0.0550 (12)
O13	0.2865 (6)	0.5264 (5)	0.3836 (3)	0.111 (2)
O14	0.5955 (5)	0.5337 (3)	0.3421 (3)	0.0655 (13)
O15	0.4930 (4)	0.2980 (3)	0.3127 (2)	0.0432 (9)
N31	−0.00665 (19)	−0.11195 (8)	1.07329 (14)	0.0521 (19)	0.500
N32	0.0280 (4)	0.25416 (14)	0.8530 (3)	0.0521 (19)	0.500
C31	0.00000	0.00000	1.00000	0.0413 (12)
C32	0.14423 (11)	0.0583 (2)	0.9163 (3)	0.0413 (12)	0.500
C33	0.1501 (3)	0.1728 (2)	0.8432 (3)	0.0413 (12)	0.500
C34	−0.1136 (3)	0.20203 (19)	0.9333 (4)	0.0413 (12)	0.500
C35	−0.12188 (16)	0.08640 (17)	1.0072 (3)	0.0413 (12)	0.500
C36	−0.1501 (3)	−0.1736 (2)	1.1571 (3)	0.098 (5)	0.500
C37	0.1136 (3)	−0.20276 (19)	1.0670 (4)	0.098 (5)	0.500
N11	0.9754 (4)	−0.0990 (4)	0.3994 (4)	0.0544 (14)
N12	1.0009 (6)	0.2582 (4)	0.1682 (4)	0.0614 (18)
C11	0.9844 (4)	0.0171 (4)	0.3236 (4)	0.0362 (12)
C12	1.1192 (5)	0.0674 (5)	0.2318 (4)	0.0488 (16)
C13	1.1231 (6)	0.1873 (5)	0.1574 (4)	0.0572 (17)
C14	0.8722 (7)	0.2147 (5)	0.2527 (6)	0.068 (2)
C15	0.8601 (5)	0.0985 (5)	0.3294 (5)	0.0567 (17)
C16	0.8358 (7)	−0.1516 (6)	0.4911 (6)	0.083 (2)
C17	1.1055 (7)	−0.1817 (6)	0.3913 (7)	0.088 (3)
Cl3	0.51832 (13)	0.21187 (10)	0.57337 (9)	0.0429 (3)
Cl4	0.07818 (14)	0.49945 (15)	0.64240 (11)	0.0727 (5)
Cl6	0.50000	0.00000	0.00000	0.0420 (5)
O1W	0.5008 (5)	0.0727 (3)	0.2546 (3)	0.0672 (13)
H111	0.14610	0.49370	0.23020	0.0790*
H112	0.23500	0.49450	0.11120	0.0790*
H121	0.48380	0.80390	0.12760	0.0820*
H122	0.46940	0.76020	0.25090	0.0820*
H131	0.23040	0.55930	0.34170	0.1670*
H132	0.23300	0.51220	0.45890	0.1670*
H141	0.55620	0.47610	0.40730	0.0980*
H142	0.68760	0.51610	0.31140	0.0980*
H151	0.50200	0.22980	0.28800	0.0650*
H152	0.50060	0.28000	0.38360	0.0650*
H32	0.23430	0.01240	0.91520	0.0490*	0.500
H32A	0.03790	0.33510	0.81110	0.0620*	0.500
H33	0.24240	0.20160	0.78040	0.0490*	0.500
H34	−0.20210	0.25030	0.93380	0.0490*	0.500
H35	−0.21530	0.05930	1.06910	0.0490*	0.500
H36A	−0.13100	−0.25800	1.20490	0.1460*	0.500
H36B	−0.21150	−0.18420	1.10930	0.1460*	0.500
H36C	−0.20330	−0.11950	1.21270	0.1460*	0.500
H37A	0.07940	−0.28050	1.13340	0.1460*	0.500
H37B	0.19810	−0.16470	1.07540	0.1460*	0.500
H37C	0.14530	−0.22520	0.98780	0.1460*	0.500
H12	1.00550	0.33520	0.11860	0.0740*
H12A	1.20780	0.01730	0.22180	0.0590*
H13	1.21510	0.22070	0.09680	0.0690*
H14	0.78600	0.26750	0.25900	0.0820*
H15	0.76560	0.07030	0.38910	0.0680*
H16A	0.78800	−0.08910	0.53910	0.1240*
H16B	0.85550	−0.23100	0.54560	0.1240*
H16C	0.76920	−0.17030	0.45080	0.1240*
H17A	1.14130	−0.20270	0.31140	0.1320*
H17B	1.07790	−0.26110	0.45660	0.1320*
H17C	1.18490	−0.13720	0.40040	0.1320*
H11W	0.49450	−0.00300	0.30050	0.1000*
H12W	0.50320	0.06830	0.18430	0.1000*

	U11	U22	U33	U12	U13	U23
Nd1	0.0410 (1)	0.0217 (1)	0.0170 (1)	0.0017 (1)	−0.0077 (1)	−0.0030 (1)
Cl1	0.0433 (5)	0.0198 (4)	0.0207 (4)	0.0021 (3)	−0.0107 (3)	−0.0029 (3)
Cl11	0.0362 (5)	0.0397 (5)	0.0472 (6)	−0.0027 (4)	−0.0187 (4)	0.0017 (4)
O11	0.0269 (15)	0.070 (2)	0.0489 (18)	0.0026 (14)	0.0025 (13)	−0.0175 (16)
O12	0.114 (3)	0.0252 (14)	0.0345 (16)	0.0054 (16)	−0.0362 (18)	−0.0082 (12)
O13	0.150 (5)	0.107 (4)	0.0282 (19)	0.053 (3)	0.013 (2)	−0.011 (2)
O14	0.118 (3)	0.0475 (19)	0.0464 (19)	0.008 (2)	−0.049 (2)	−0.0110 (15)
O15	0.075 (2)	0.0263 (14)	0.0281 (14)	−0.0017 (14)	−0.0222 (14)	0.0009 (11)
N31	0.061 (4)	0.033 (3)	0.056 (3)	−0.002 (3)	−0.021 (3)	0.002 (2)
N32	0.061 (4)	0.033 (3)	0.056 (3)	−0.002 (3)	−0.021 (3)	0.002 (2)
C31	0.031 (2)	0.041 (2)	0.047 (2)	0.0040 (17)	−0.0102 (17)	−0.0080 (18)
C32	0.031 (2)	0.041 (2)	0.047 (2)	0.0040 (17)	−0.0102 (17)	−0.0080 (18)
C33	0.031 (2)	0.041 (2)	0.047 (2)	0.0040 (17)	−0.0102 (17)	−0.0080 (18)
C34	0.031 (2)	0.041 (2)	0.047 (2)	0.0040 (17)	−0.0102 (17)	−0.0080 (18)
C35	0.031 (2)	0.041 (2)	0.047 (2)	0.0040 (17)	−0.0102 (17)	−0.0080 (18)
C36	0.091 (8)	0.081 (8)	0.096 (9)	0.004 (6)	−0.028 (7)	0.014 (7)
C37	0.091 (8)	0.081 (8)	0.096 (9)	0.004 (6)	−0.028 (7)	0.014 (7)
N11	0.050 (2)	0.044 (2)	0.060 (3)	−0.0031 (18)	−0.0208 (19)	0.0069 (19)
N12	0.093 (4)	0.035 (2)	0.064 (3)	−0.006 (2)	−0.042 (3)	−0.0022 (19)
C11	0.035 (2)	0.033 (2)	0.037 (2)	−0.0004 (16)	−0.0106 (17)	−0.0046 (17)
C12	0.034 (2)	0.054 (3)	0.051 (3)	−0.001 (2)	−0.008 (2)	−0.009 (2)
C13	0.061 (3)	0.060 (3)	0.043 (3)	−0.027 (3)	−0.009 (2)	−0.003 (2)
C14	0.073 (4)	0.048 (3)	0.080 (4)	0.024 (3)	−0.030 (3)	−0.013 (3)
C15	0.041 (3)	0.056 (3)	0.060 (3)	0.012 (2)	−0.009 (2)	−0.007 (2)
C16	0.074 (4)	0.084 (4)	0.066 (4)	−0.033 (3)	−0.018 (3)	0.024 (3)
C17	0.081 (4)	0.056 (4)	0.117 (6)	0.021 (3)	−0.047 (4)	0.008 (4)
Cl3	0.0650 (7)	0.0375 (5)	0.0298 (5)	0.0030 (5)	−0.0210 (5)	−0.0083 (4)
Cl4	0.0507 (7)	0.0898 (10)	0.0383 (6)	0.0214 (7)	0.0100 (5)	0.0094 (6)
Cl6	0.0588 (9)	0.0270 (7)	0.0404 (8)	−0.0014 (6)	−0.0198 (7)	−0.0040 (6)
O1W	0.128 (3)	0.0297 (16)	0.050 (2)	0.0021 (19)	−0.042 (2)	−0.0041 (14)

Nd1—Cl1	2.8298 (8)	N12—H12	0.8800
Nd1—Cl11	2.7852 (11)	C31—C35ii	1.417 (2)
Nd1—O11	2.429 (3)	C31—C32ii	1.467 (2)
Nd1—O12	2.426 (3)	C31—C35	1.417 (2)
Nd1—O13	2.477 (4)	C31—C32	1.467 (2)
Nd1—O14	2.479 (4)	C32—C33	1.306 (4)
Nd1—O15	2.404 (3)	C34—C35	1.318 (4)
Nd1—Cl1i	2.8345 (9)	C32—H32	0.9500
O11—H111	0.8500	C33—H33	0.9500
O11—H112	0.8500	C34—H34	0.9500
O12—H121	0.8500	C35—H35	0.9500
O12—H122	0.8500	C36—H36B	0.9800
O13—H131	0.8500	C36—H36C	0.9800
O13—H132	0.8500	C36—H36A	0.9800
O14—H141	0.8500	C37—H37A	0.9800
O14—H142	0.8500	C37—H37B	0.9800
O15—H151	0.8500	C37—H37C	0.9800
O15—H152	0.8500	C11—C15	1.404 (7)
N31—C31	1.2855 (12)	C11—C12	1.408 (6)
N31—C36	1.474 (4)	C12—C13	1.360 (7)
N31—C37	1.435 (3)	C14—C15	1.333 (8)
N32—C33	1.385 (4)	C12—H12A	0.9500
N32—C34	1.418 (5)	C13—H13	0.9500
O1W—H12W	0.8500	C14—H14	0.9500
O1W—H11W	0.8500	C15—H15	0.9500
N32—H32A	0.8800	C16—H16B	0.9800
N11—C11	1.330 (6)	C16—H16C	0.9800
N11—C17	1.452 (8)	C16—H16A	0.9800
N11—C16	1.446 (8)	C17—H17C	0.9800
N12—C13	1.322 (8)	C17—H17A	0.9800
N12—C14	1.319 (9)	C17—H17B	0.9800
Cl1—Nd1—Cl11	81.28 (3)	C32—C31—C35ii	66.36 (14)
Cl1—Nd1—O11	74.96 (8)	C32—C31—C32ii	180.00
Cl1—Nd1—O12	69.82 (8)	C35—C31—C35ii	180.00
Cl1—Nd1—O13	124.05 (12)	C32ii—C31—C35ii	113.64 (14)
Cl1—Nd1—O14	134.06 (8)	N31ii—C31—C32	58.94 (12)
Cl1—Nd1—O15	146.10 (7)	N31—C31—C35ii	55.70 (14)
Cl1—Nd1—Cl1i	74.27 (2)	C32ii—C31—C35	66.36 (14)
Cl11—Nd1—O11	148.14 (8)	C32—C31—C35	113.64 (14)
Cl11—Nd1—O12	94.54 (9)	N31ii—C31—C35ii	124.30 (14)
Cl11—Nd1—O13	144.01 (13)	N31ii—C31—C32ii	121.06 (12)
Cl11—Nd1—O14	74.88 (10)	C31—C32—C33	120.66 (19)
Cl11—Nd1—O15	91.79 (9)	N32—C33—C32	123.0 (3)
Cl1i—Nd1—Cl11	79.91 (3)	N32—C34—C35	119.7 (3)
O11—Nd1—O12	96.80 (12)	C31—C35—C34	124.0 (3)
O11—Nd1—O13	67.84 (15)	C33—C32—H32	120.00
O11—Nd1—O14	136.94 (12)	C31—C32—H32	120.00
O11—Nd1—O15	96.19 (12)	C32—C33—H33	119.00
Cl1i—Nd1—O11	73.49 (8)	N32—C33—H33	118.00
O12—Nd1—O13	74.71 (15)	N32—C34—H34	120.00
O12—Nd1—O14	73.57 (12)	C35—C34—H34	120.00
O12—Nd1—O15	144.06 (10)	C31—C35—H35	118.00
Cl1i—Nd1—O12	144.08 (8)	C34—C35—H35	118.00
O13—Nd1—O14	69.15 (16)	H36A—C36—H36B	109.00
O13—Nd1—O15	79.52 (14)	H36A—C36—H36C	109.00
Cl1i—Nd1—O13	128.31 (13)	N31—C36—H36C	109.00
O14—Nd1—O15	74.08 (11)	N31—C36—H36A	110.00
Cl1i—Nd1—O14	136.47 (9)	H36B—C36—H36C	109.00
Cl1i—Nd1—O15	71.85 (7)	N31—C36—H36B	109.00
Nd1—Cl1—Nd1i	105.74 (3)	H37B—C37—H37C	109.00
Nd1—O11—H111	137.00	H37A—C37—H37C	109.00
Nd1—O11—H112	113.00	N31—C37—H37B	110.00
H111—O11—H112	109.00	N31—C37—H37A	109.00
Nd1—O12—H121	130.00	H37A—C37—H37B	110.00
Nd1—O12—H122	119.00	N31—C37—H37C	109.00
H121—O12—H122	110.00	C12—C11—C15	115.1 (4)
Nd1—O13—H131	88.00	N11—C11—C15	122.4 (4)
Nd1—O13—H132	163.00	N11—C11—C12	122.5 (4)
H131—O13—H132	108.00	C11—C12—C13	120.3 (5)
Nd1—O14—H141	107.00	N12—C13—C12	121.1 (5)
Nd1—O14—H142	104.00	N12—C14—C15	121.7 (6)
H141—O14—H142	109.00	C11—C15—C14	121.2 (5)
Nd1—O15—H151	125.00	C11—C12—H12A	120.00
Nd1—O15—H152	125.00	C13—C12—H12A	120.00
H151—O15—H152	109.00	C12—C13—H13	119.00
C31—N31—C36	122.21 (17)	N12—C13—H13	119.00
C31—N31—C37	125.7 (2)	N12—C14—H14	119.00
C36—N31—C37	110.75 (19)	C15—C14—H14	119.00
C33—N32—C34	117.4 (2)	C14—C15—H15	119.00
H11W—O1W—H12W	109.00	C11—C15—H15	119.00
C34—N32—H32A	121.00	N11—C16—H16A	109.00
C33—N32—H32A	121.00	N11—C16—H16B	109.00
C11—N11—C16	122.2 (4)	H16A—C16—H16B	109.00
C11—N11—C17	121.4 (5)	H16A—C16—H16C	109.00
C16—N11—C17	116.4 (5)	N11—C16—H16C	109.00
C13—N12—C14	120.6 (5)	H16B—C16—H16C	109.00
C13—N12—H12	120.00	N11—C17—H17B	109.00
C14—N12—H12	120.00	N11—C17—H17C	109.00
N31—C31—C35	124.30 (14)	N11—C17—H17A	109.00
N31—C31—C32	121.06 (12)	H17A—C17—H17C	109.00
N31—C31—N31ii	180.00	H17B—C17—H17C	110.00
N31ii—C31—C35	55.70 (14)	H17A—C17—H17B	109.00
N31—C31—C32ii	58.94 (12)
Cl11—Nd1—Cl1—Nd1i	81.90 (4)	C33—N32—C34—C35	9.3 (5)
O11—Nd1—Cl1—Nd1i	−76.70 (9)	C16—N11—C11—C12	−178.2 (5)
O12—Nd1—Cl1—Nd1i	−179.96 (10)	C16—N11—C11—C15	1.9 (7)
O13—Nd1—Cl1—Nd1i	−125.94 (16)	C17—N11—C11—C12	−0.3 (7)
O14—Nd1—Cl1—Nd1i	140.86 (13)	C17—N11—C11—C15	179.8 (5)
O15—Nd1—Cl1—Nd1i	1.78 (17)	C14—N12—C13—C12	0.8 (8)
Cl1i—Nd1—Cl1—Nd1i	0.00 (4)	C13—N12—C14—C15	−0.3 (9)
Cl1—Nd1—Cl1i—Nd1i	0.00 (3)	N31ii—C31—C32—C33	0.9 (2)
Cl11—Nd1—Cl1i—Nd1i	−83.69 (4)	C35—C31—C32—C33	−10.1 (3)
O11—Nd1—Cl1i—Nd1i	78.59 (9)	N31—C31—C32—C33	−179.1 (2)
O12—Nd1—Cl1i—Nd1i	0.06 (16)	C32—C31—C35—C34	10.0 (3)
O13—Nd1—Cl1i—Nd1i	121.24 (15)	C35ii—C31—C32—C33	169.9 (3)
O14—Nd1—Cl1i—Nd1i	−138.80 (13)	N31—C31—C35—C34	178.6 (2)
O15—Nd1—Cl1i—Nd1i	−178.95 (10)	N31ii—C31—C35—C34	−1.4 (2)
C36—N31—C31—C32	−179.1 (2)	C32ii—C31—C35—C34	−170.0 (3)
C36—N31—C31—C35	13.0 (2)	C31—C32—C33—N32	11.0 (4)
C36—N31—C31—C32ii	0.88 (19)	N32—C34—C35—C31	−10.1 (5)
C36—N31—C31—C35ii	−167.0 (2)	N11—C11—C12—C13	−179.2 (5)
C37—N31—C31—C32	−13.5 (3)	C15—C11—C12—C13	0.7 (7)
C37—N31—C31—C35	178.6 (2)	N11—C11—C15—C14	179.7 (5)
C37—N31—C31—C32ii	166.5 (3)	C12—C11—C15—C14	−0.3 (8)
C37—N31—C31—C35ii	−1.4 (2)	C11—C12—C13—N12	−1.0 (8)
C34—N32—C33—C32	−10.2 (5)	N12—C14—C15—C11	0.1 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H111···Cl4iii	0.85	2.16	3.010 (3)	177
O11—H112···Cl11i	0.85	2.30	3.149 (4)	173
O12—H121···Cl6iv	0.85	2.24	3.080 (3)	168
O12—H122···Cl3v	0.85	2.25	3.089 (3)	171
O13—H131···O11	0.85	2.19	2.738 (6)	122
O13—H131···Cl4iii	0.85	2.99	3.631 (6)	134
O13—H132···Cl4	0.85	2.16	3.005 (4)	172
O14—H142···Cl4v	0.85	2.46	3.159 (4)	140
O14—H142···Cl11	0.85	2.73	3.210 (4)	118
O15—H151···O1W	0.85	1.84	2.683 (4)	172
O15—H152···Cl3	0.85	2.26	3.109 (3)	175
N12—H12···Cl11vi	0.88	2.65	3.358 (5)	138
N12—H12···Cl11	0.88	2.78	3.451 (5)	134
O1W—H11W···Cl3vii	0.85	2.35	3.197 (3)	179
O1W—H12W···Cl6	0.85	2.52	3.349 (3)	167
N32—H32A···Cl4	0.88	2.26	3.0808 (16)	156
C34—H34···Cl1iii	0.95	2.82	3.703 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H111⋯Cl4i	0.85	2.16	3.010 (3)	177
O11—H112⋯Cl11ii	0.85	2.30	3.149 (4)	173
O12—H121⋯Cl6iii	0.85	2.24	3.080 (3)	168
O12—H122⋯Cl3iv	0.85	2.25	3.089 (3)	171
O13—H131⋯O11	0.85	2.19	2.738 (6)	122
O13—H131⋯Cl4i	0.85	2.99	3.631 (6)	134
O13—H132⋯Cl4	0.85	2.16	3.005 (4)	172
O14—H142⋯Cl4iv	0.85	2.46	3.159 (4)	140
O14—H142⋯Cl11	0.85	2.73	3.210 (4)	118
O15—H151⋯O1W	0.85	1.84	2.683 (4)	172
O15—H152⋯Cl3	0.85	2.26	3.109 (3)	175
N12—H12⋯Cl11v	0.88	2.65	3.358 (5)	138
N12—H12⋯Cl11	0.88	2.78	3.451 (5)	134
O1W—H11W⋯Cl3vi	0.85	2.35	3.197 (3)	179
O1W—H12W⋯Cl6	0.85	2.52	3.349 (3)	167
N32—H32A⋯Cl4	0.88	2.26	3.0808 (16)	156
C34—H34⋯Cl1i	0.95	2.82	3.703 (3)	155

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