Redetermination of 1,3-diammonio-1,2,3-tride-oxy-cis-inositol dichloride.

The crystal structure of the title compound, C(6)H(16)N(2)O(3) (2+)·2Cl(-), has been reported previously by Palm [Acta Cryst. (1967 ▶), 22, 209-216] from Weisenberg camera data, with R1 = 10.5%, isotropic refinement of non-H atoms and H atoms not located. We remeasured a data set of the title compound and present a more precise structure determination. The asymmetric unit contains two unique 1,3-diammonio-1,2,3-tride-oxy-cis-inositol cations and four Cl(-) counter-ions. The cyclo-hexane rings of both inositol cations adopt chair conformations with two axial hy-droxy groups. An extended network of hydrogen bonds is formed. The four chloride counter ions are hydrogen bonded to the hydroxy and ammonium groups of the cations by N-H⋯Cl and O-H⋯Cl interactions. The cations are aligned into wavy layers by cation⋯cation interactions of the form N-H⋯O(ax), N-H⋯O(eq) and O(ax)-H⋯O(eq). Intramolecular hydrogen bonding between the axial hydroxy groups is, however, not observed.

Related literature

An earlier, less accurate structure determination of the title compound was performed by Palm (1967 ▶). The crystal structure of 1,3-diammonio-1,2,3-tride­oxy-cis-inositol sulfate has been reported by Neis et al. (2012 ▶). The importance of intra­molecular n class="Chemical">hydrogen bonding in 1,3,5-tris­ubstituted cyclo­hexane derivatives has been described by Gencheva et al. (2000 ▶), Saaidi et al. (2008 ▶) and Neis et al. (2010 ▶), and the implication of increased 1,3-diaxial repulsion on the conformation of a cyclo­hexane ring has been discussed by Fritsche-Lang et al. (1985 ▶), Kramer et al. (1998 ▶) and Kuppert et al. (2006 ▶). For the synthesis, see: Merten et al. (2012 ▶). For the treatment of hydrogen atoms in SHELXL, see: Müller et al. (2006 ▶).

Experimental

Crystal data

C6H16N2O3 2+·2Cl−

M = 235.11

Monoclinic,

a = 7.7899 (4) Å

b = 10.1254 (5) Å

c = 13.0136 (7) Å

β = 91.156 (2)°

V = 1026.25 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.61 mm−1

T = 130 K

0.30 × 0.22 × 0.15 mm

Data collection

Bruker–Nonius X8 APEX KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.838, T max = 0.914

16242 measured reflections

4459 independent reflections

4429 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.047

S = 1.06

4459 reflections

289 parameters

19 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack (1983 ▶), 2093 Friedel pairs

Flack parameter: 0.01 (3)

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012366/sj5213sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012366/sj5213Isup2.hkl

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

C6H16N2O32+·2Cl−	F(000) = 496
Mr = 235.11	Dx = 1.522 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9336 reflections
a = 7.7899 (4) Å	θ = 2.6–40.5°
b = 10.1254 (5) Å	µ = 0.61 mm−1
c = 13.0136 (7) Å	T = 130 K
β = 91.156 (2)°	Prism, colorless
V = 1026.25 (9) Å3	0.30 × 0.22 × 0.15 mm
Z = 4

Bruker–Nonius X8 APEX KappaCCD diffractometer	4459 independent reflections
Radiation source: fine-focus sealed tube	4429 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −9→9
Tmin = 0.838, Tmax = 0.914	k = −12→12
16242 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.017	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.047	w = 1/[σ2(Fo2) + (0.0292P)2 + 0.1788P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4459 reflections	Δρmax = 0.27 e Å−3
289 parameters	Δρmin = −0.15 e Å−3
19 restraints	Absolute structure: Flack (1983), 2093 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (3)

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.

	x	y	z	Uiso*/Ueq
C1	0.65695 (15)	0.78053 (13)	0.49259 (9)	0.0116 (2)
H1A	0.7440	0.8297	0.4535	0.014*
H1B	0.6742	0.6850	0.4805	0.014*
C2	0.47789 (15)	0.82069 (11)	0.45618 (9)	0.0109 (2)
H2	0.4629	0.9177	0.4672	0.013*
C3	0.33980 (16)	0.74645 (11)	0.51435 (9)	0.0117 (2)
H3	0.2245	0.7822	0.4936	0.014*
C4	0.36884 (16)	0.76840 (13)	0.63009 (9)	0.0135 (2)
H4	0.3478	0.8638	0.6453	0.016*
C5	0.54882 (17)	0.73308 (12)	0.66995 (9)	0.0141 (2)
H5	0.5605	0.7597	0.7438	0.017*
C6	0.67808 (15)	0.81082 (12)	0.60699 (9)	0.0129 (2)
H6	0.6605	0.9075	0.6185	0.015*
N18	0.72743 (14)	1.01783 (11)	0.05624 (8)	0.0149 (2)
H18A	0.6277 (19)	1.0191 (18)	0.0889 (12)	0.022*
H18B	0.789 (2)	1.0895 (16)	0.0746 (14)	0.022*
H18C	0.706 (2)	1.0188 (19)	−0.0129 (10)	0.022*
N22	0.73895 (14)	0.53468 (11)	0.10007 (8)	0.0154 (2)
H22C	0.706 (2)	0.5268 (19)	0.0357 (11)	0.023*
H22A	0.801 (2)	0.4651 (17)	0.1183 (13)	0.023*
H22B	0.646 (2)	0.5385 (19)	0.1356 (13)	0.023*
O19	0.75839 (12)	0.93190 (9)	0.26803 (7)	0.01429 (18)
H19	0.751 (2)	1.0080 (15)	0.2863 (13)	0.021*
O20	1.09187 (12)	0.81557 (10)	0.32436 (7)	0.0206 (2)
H20	1.028 (2)	0.8689 (19)	0.3606 (14)	0.031*
O21	0.78841 (12)	0.64823 (10)	0.28780 (7)	0.01674 (19)
H21	0.837 (2)	0.6185 (18)	0.3397 (12)	0.025*
N7	0.45629 (14)	0.79085 (11)	0.34387 (8)	0.0132 (2)
H7C	0.3542 (19)	0.8197 (17)	0.3215 (13)	0.020*
H7B	0.537 (2)	0.8271 (17)	0.3103 (13)	0.020*
H7A	0.462 (2)	0.7050 (14)	0.3315 (13)	0.020*
C13	0.83453 (16)	0.90192 (12)	0.08871 (9)	0.0140 (2)
H13	0.9361	0.8970	0.0431	0.017*
O8	0.34834 (12)	0.61091 (9)	0.48626 (7)	0.01400 (17)
H8	0.2471 (19)	0.5838 (18)	0.4902 (14)	0.021*
C14	0.89926 (16)	0.92022 (12)	0.19938 (9)	0.0131 (2)
H14	0.9704	1.0023	0.2037	0.016*
O9	0.24058 (12)	0.69200 (10)	0.68068 (7)	0.01881 (19)
H9	0.213 (2)	0.7301 (18)	0.7312 (13)	0.028*
C15	1.01194 (16)	0.80171 (13)	0.22624 (9)	0.0152 (2)
H15	1.1064	0.8011	0.1754	0.018*
O10	0.58596 (14)	0.59647 (10)	0.66089 (7)	0.0204 (2)
H10	0.601 (2)	0.5671 (19)	0.7219 (12)	0.031*
C16	0.92115 (16)	0.66793 (12)	0.21605 (9)	0.0134 (2)
H16	1.0084	0.5963	0.2255	0.016*
N11	0.85723 (14)	0.77409 (13)	0.63986 (8)	0.0182 (2)
H11C	0.931 (2)	0.8269 (18)	0.6089 (14)	0.027*
H11B	0.872 (2)	0.780 (2)	0.7055 (11)	0.027*
H11A	0.883 (2)	0.6931 (16)	0.6164 (14)	0.027*
C17	0.84314 (16)	0.65722 (12)	0.10753 (9)	0.0132 (2)
H17	0.9392	0.6500	0.0580	0.016*
C12	0.73148 (16)	0.77507 (13)	0.07590 (9)	0.0137 (2)
H12A	0.6929	0.7652	0.0033	0.016*
H12B	0.6285	0.7786	0.1192	0.016*
Cl1	0.95255 (4)	0.27346 (3)	0.13119 (2)	0.01574 (7)
Cl2	0.96850 (3)	0.51134 (3)	0.48456 (2)	0.01623 (6)
Cl3	0.36075 (4)	0.53635 (3)	0.18167 (2)	0.02006 (7)
Cl4	0.34728 (4)	0.98731 (3)	0.12868 (2)	0.02147 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0106 (5)	0.0148 (6)	0.0092 (5)	−0.0009 (4)	−0.0005 (4)	0.0008 (4)
C2	0.0121 (5)	0.0109 (5)	0.0096 (5)	−0.0002 (4)	−0.0004 (4)	−0.0002 (4)
C3	0.0111 (5)	0.0103 (5)	0.0138 (5)	0.0004 (4)	0.0021 (4)	−0.0004 (4)
C4	0.0166 (6)	0.0108 (5)	0.0134 (5)	−0.0016 (4)	0.0059 (4)	−0.0001 (4)
C5	0.0203 (6)	0.0122 (5)	0.0097 (5)	−0.0014 (5)	0.0021 (4)	0.0003 (4)
C6	0.0138 (6)	0.0140 (6)	0.0107 (5)	−0.0020 (4)	−0.0015 (4)	0.0004 (4)
N18	0.0175 (5)	0.0141 (5)	0.0131 (4)	−0.0007 (4)	−0.0003 (4)	0.0020 (4)
N22	0.0177 (5)	0.0142 (5)	0.0140 (5)	0.0010 (4)	−0.0013 (4)	−0.0019 (4)
O19	0.0168 (4)	0.0137 (4)	0.0125 (4)	0.0013 (3)	0.0033 (3)	−0.0020 (3)
O20	0.0189 (5)	0.0250 (5)	0.0176 (4)	0.0031 (4)	−0.0048 (4)	−0.0033 (4)
O21	0.0170 (5)	0.0219 (5)	0.0114 (4)	0.0020 (4)	0.0003 (3)	0.0017 (3)
N7	0.0133 (5)	0.0159 (5)	0.0104 (5)	−0.0016 (4)	−0.0012 (4)	0.0010 (4)
C13	0.0158 (6)	0.0136 (6)	0.0125 (5)	0.0003 (4)	0.0017 (4)	0.0005 (4)
O8	0.0129 (4)	0.0115 (4)	0.0177 (4)	−0.0025 (3)	0.0029 (3)	−0.0030 (3)
C14	0.0113 (5)	0.0139 (6)	0.0140 (6)	−0.0012 (4)	0.0011 (4)	−0.0014 (4)
O9	0.0214 (5)	0.0175 (5)	0.0180 (4)	−0.0036 (4)	0.0115 (4)	−0.0020 (4)
C15	0.0115 (5)	0.0173 (6)	0.0167 (6)	0.0015 (4)	−0.0028 (4)	−0.0033 (5)
O10	0.0302 (5)	0.0148 (4)	0.0162 (4)	0.0005 (4)	−0.0002 (4)	0.0018 (4)
C16	0.0128 (6)	0.0142 (6)	0.0133 (5)	0.0022 (4)	−0.0005 (4)	−0.0003 (4)
N11	0.0171 (5)	0.0222 (6)	0.0151 (5)	−0.0032 (5)	−0.0055 (4)	0.0027 (5)
C17	0.0135 (6)	0.0133 (6)	0.0127 (5)	0.0000 (4)	0.0021 (4)	−0.0020 (4)
C12	0.0166 (5)	0.0144 (6)	0.0101 (5)	0.0001 (5)	−0.0015 (4)	−0.0010 (4)
Cl1	0.01912 (14)	0.01465 (13)	0.01360 (12)	−0.00009 (11)	0.00369 (10)	0.00124 (10)
Cl2	0.01362 (13)	0.01454 (13)	0.02052 (14)	−0.00019 (10)	0.00009 (10)	0.00263 (11)
Cl3	0.01973 (14)	0.02535 (17)	0.01513 (13)	−0.00115 (12)	0.00145 (10)	−0.00093 (12)
Cl4	0.01848 (14)	0.03068 (18)	0.01520 (13)	−0.00287 (12)	−0.00074 (10)	0.00097 (12)

C1—C2	1.5195 (16)	O19—H19	0.809 (15)
C1—C6	1.5257 (15)	O20—C15	1.4163 (15)
C1—H1A	0.9900	O20—H20	0.878 (15)
C1—H1B	0.9900	O21—C16	1.4212 (15)
C2—N7	1.4987 (14)	O21—H21	0.825 (14)
C2—C3	1.5258 (16)	N7—H7C	0.890 (14)
C2—H2	1.0000	N7—H7B	0.852 (14)
C3—O8	1.4222 (14)	N7—H7A	0.885 (14)
C3—C4	1.5347 (16)	C13—C12	1.5221 (18)
C3—H3	1.0000	C13—C14	1.5275 (16)
C4—O9	1.4341 (14)	C13—H13	1.0000
C4—C5	1.5275 (18)	O8—H8	0.838 (14)
C4—H4	1.0000	C14—C15	1.5232 (17)
C5—O10	1.4186 (15)	C14—H14	1.0000
C5—C6	1.5291 (16)	O9—H9	0.796 (15)
C5—H5	1.0000	C15—C16	1.5326 (17)
C6—N11	1.4983 (16)	C15—H15	1.0000
C6—H6	1.0000	O10—H10	0.854 (15)
N18—C13	1.4959 (16)	C16—C17	1.5299 (16)
N18—H18A	0.893 (14)	C16—H16	1.0000
N18—H18B	0.900 (14)	N11—H11C	0.885 (15)
N18—H18C	0.911 (13)	N11—H11B	0.862 (14)
N22—C17	1.4848 (16)	N11—H11A	0.898 (15)
N22—H22C	0.874 (14)	C17—C12	1.5283 (17)
N22—H22A	0.883 (15)	C17—H17	1.0000
N22—H22B	0.865 (14)	C12—H12A	0.9900
O19—C14	1.4339 (15)	C12—H12B	0.9900
C2—C1—C6	109.31 (10)	C2—N7—H7C	109.6 (11)
C2—C1—H1A	109.8	C2—N7—H7B	110.1 (12)
C6—C1—H1A	109.8	H7C—N7—H7B	110.5 (16)
C2—C1—H1B	109.8	C2—N7—H7A	111.7 (12)
C6—C1—H1B	109.8	H7C—N7—H7A	107.9 (17)
H1A—C1—H1B	108.3	H7B—N7—H7A	106.9 (17)
N7—C2—C1	109.54 (9)	N18—C13—C12	109.95 (10)
N7—C2—C3	108.55 (9)	N18—C13—C14	110.05 (10)
C1—C2—C3	111.43 (9)	C12—C13—C14	111.65 (10)
N7—C2—H2	109.1	N18—C13—H13	108.4
C1—C2—H2	109.1	C12—C13—H13	108.4
C3—C2—H2	109.1	C14—C13—H13	108.4
O8—C3—C2	108.11 (9)	C3—O8—H8	104.6 (12)
O8—C3—C4	112.66 (10)	O19—C14—C15	111.51 (10)
C2—C3—C4	108.91 (10)	O19—C14—C13	110.81 (10)
O8—C3—H3	109.0	C15—C14—C13	107.37 (10)
C2—C3—H3	109.0	O19—C14—H14	109.0
C4—C3—H3	109.0	C15—C14—H14	109.0
O9—C4—C5	111.16 (10)	C13—C14—H14	109.0
O9—C4—C3	106.39 (10)	C4—O9—H9	108.6 (14)
C5—C4—C3	114.55 (10)	O20—C15—C14	111.69 (10)
O9—C4—H4	108.2	O20—C15—C16	111.06 (10)
C5—C4—H4	108.2	C14—C15—C16	114.43 (10)
C3—C4—H4	108.2	O20—C15—H15	106.4
O10—C5—C4	112.79 (10)	C14—C15—H15	106.4
O10—C5—C6	108.65 (10)	C16—C15—H15	106.4
C4—C5—C6	107.90 (10)	C5—O10—H10	106.7 (13)
O10—C5—H5	109.1	O21—C16—C17	108.41 (10)
C4—C5—H5	109.1	O21—C16—C15	114.07 (10)
C6—C5—H5	109.1	C17—C16—C15	108.45 (10)
N11—C6—C1	108.07 (10)	O21—C16—H16	108.6
N11—C6—C5	109.81 (10)	C17—C16—H16	108.6
C1—C6—C5	111.11 (10)	C15—C16—H16	108.6
N11—C6—H6	109.3	C6—N11—H11C	109.0 (12)
C1—C6—H6	109.3	C6—N11—H11B	111.6 (13)
C5—C6—H6	109.3	H11C—N11—H11B	109.4 (18)
C13—N18—H18A	111.2 (12)	C6—N11—H11A	109.9 (12)
C13—N18—H18B	105.4 (12)	H11C—N11—H11A	104.3 (17)
H18A—N18—H18B	109.1 (17)	H11B—N11—H11A	112.3 (18)
C13—N18—H18C	112.1 (11)	N22—C17—C12	109.12 (10)
H18A—N18—H18C	109.2 (15)	N22—C17—C16	109.03 (10)
H18B—N18—H18C	109.8 (17)	C12—C17—C16	113.99 (10)
C17—N22—H22C	106.7 (12)	N22—C17—H17	108.2
C17—N22—H22A	110.8 (12)	C12—C17—H17	108.2
H22C—N22—H22A	109.4 (17)	C16—C17—H17	108.2
C17—N22—H22B	112.8 (13)	C13—C12—C17	109.47 (10)
H22C—N22—H22B	106.6 (16)	C13—C12—H12A	109.8
H22A—N22—H22B	110.3 (17)	C17—C12—H12A	109.8
C14—O19—H19	108.9 (13)	C13—C12—H12B	109.8
C15—O20—H20	107.5 (13)	C17—C12—H12B	109.8
C16—O21—H21	105.0 (13)	H12A—C12—H12B	108.2
C6—C1—C2—N7	−179.87 (10)	N18—C13—C14—O19	59.93 (13)
C6—C1—C2—C3	−59.74 (13)	C12—C13—C14—O19	−62.45 (13)
N7—C2—C3—O8	53.24 (12)	N18—C13—C14—C15	−178.07 (10)
C1—C2—C3—O8	−67.46 (12)	C12—C13—C14—C15	59.55 (13)
N7—C2—C3—C4	175.96 (9)	O19—C14—C15—O20	−64.11 (13)
C1—C2—C3—C4	55.26 (12)	C13—C14—C15—O20	174.33 (10)
O8—C3—C4—O9	−57.58 (13)	O19—C14—C15—C16	63.16 (13)
C2—C3—C4—O9	−177.52 (9)	C13—C14—C15—C16	−58.41 (13)
O8—C3—C4—C5	65.65 (14)	O20—C15—C16—O21	61.04 (13)
C2—C3—C4—C5	−54.29 (13)	C14—C15—C16—O21	−66.54 (13)
O9—C4—C5—O10	55.85 (13)	O20—C15—C16—C17	−178.05 (10)
C3—C4—C5—O10	−64.77 (13)	C14—C15—C16—C17	54.36 (13)
O9—C4—C5—C6	175.88 (9)	O21—C16—C17—N22	−49.61 (13)
C3—C4—C5—C6	55.25 (13)	C15—C16—C17—N22	−173.95 (10)
C2—C1—C6—N11	−178.30 (10)	O21—C16—C17—C12	72.58 (13)
C2—C1—C6—C5	61.17 (13)	C15—C16—C17—C12	−51.77 (13)
O10—C5—C6—N11	−54.54 (13)	N18—C13—C12—C17	179.03 (10)
C4—C5—C6—N11	−177.14 (10)	C14—C13—C12—C17	−58.53 (13)
O10—C5—C6—C1	64.96 (13)	N22—C17—C12—C13	177.03 (10)
C4—C5—C6—C1	−57.64 (13)	C16—C17—C12—C13	54.90 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N18—H18A···Cl4	0.89 (1)	2.28 (1)	3.1411 (11)	163 (2)
N18—H18B···Cl1i	0.90 (1)	2.37 (2)	3.2646 (12)	177 (2)
N18—H18C···Cl3ii	0.91 (1)	2.26 (1)	3.1634 (11)	175 (2)
N22—H22C···Cl4iii	0.87 (1)	2.21 (1)	3.0761 (11)	172 (2)
N22—H22A···Cl1	0.88 (2)	2.28 (2)	3.1466 (12)	168 (2)
N22—H22B···Cl3	0.87 (1)	2.32 (2)	3.1518 (12)	162 (2)
O19—H19···O9iv	0.81 (2)	1.91 (2)	2.7168 (13)	172 (2)
O20—H20···Cl2v	0.88 (2)	2.48 (2)	3.2220 (10)	143 (2)
O21—H21···Cl2	0.83 (1)	2.39 (2)	3.2096 (10)	174 (2)
N7—H7C···O20vi	0.89 (1)	2.05 (2)	2.8560 (15)	151 (2)
N7—H7B···O19	0.85 (1)	2.11 (2)	2.9404 (14)	164 (2)
N7—H7A···Cl3	0.89 (1)	2.70 (2)	3.4038 (11)	138 (1)
O8—H8···Cl2vi	0.84 (1)	2.29 (2)	3.1256 (10)	175 (2)
O9—H9···Cl1iv	0.80 (2)	2.27 (2)	3.0144 (10)	156 (2)
O10—H10···Cl4vii	0.85 (2)	2.14 (2)	2.9889 (10)	177 (2)
N11—H11C···Cl2v	0.89 (2)	2.37 (2)	3.2132 (12)	159 (2)
N11—H11B···Cl1v	0.86 (1)	2.51 (2)	3.3007 (11)	154 (2)
N11—H11A···Cl2	0.90 (2)	2.61 (2)	3.4618 (13)	158 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N18—H18A⋯Cl4	0.89 (1)	2.28 (1)	3.1411 (11)	163 (2)
N18—H18B⋯Cl1i	0.90 (1)	2.37 (2)	3.2646 (12)	177 (2)
N18—H18C⋯Cl3ii	0.91 (1)	2.26 (1)	3.1634 (11)	175 (2)
N22—H22C⋯Cl4iii	0.87 (1)	2.21 (1)	3.0761 (11)	172 (2)
N22—H22A⋯Cl1	0.88 (2)	2.28 (2)	3.1466 (12)	168 (2)
N22—H22B⋯Cl3	0.87 (1)	2.32 (2)	3.1518 (12)	162 (2)
O19—H19⋯O9iv	0.81 (2)	1.91 (2)	2.7168 (13)	172 (2)
O20—H20⋯Cl2v	0.88 (2)	2.48 (2)	3.2220 (10)	143 (2)
O21—H21⋯Cl2	0.83 (1)	2.39 (2)	3.2096 (10)	174 (2)
N7—H7C⋯O20vi	0.89 (1)	2.05 (2)	2.8560 (15)	151 (2)
N7—H7B⋯O19	0.85 (1)	2.11 (2)	2.9404 (14)	164 (2)
N7—H7A⋯Cl3	0.89 (1)	2.70 (2)	3.4038 (11)	138 (1)
O8—H8⋯Cl2vi	0.84 (1)	2.29 (2)	3.1256 (10)	175 (2)
O9—H9⋯Cl1iv	0.80 (2)	2.27 (2)	3.0144 (10)	156 (2)
O10—H10⋯Cl4vii	0.85 (2)	2.14 (2)	2.9889 (10)	177 (2)
N11—H11C⋯Cl2v	0.89 (2)	2.37 (2)	3.2132 (12)	159 (2)
N11—H11B⋯Cl1v	0.86 (1)	2.51 (2)	3.3007 (11)	154 (2)
N11—H11A⋯Cl2	0.90 (2)	2.61 (2)	3.4618 (13)	158 (2)

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