1,12-Bis(2-carboxy-phen-yl)-5,8-dioxa-2,11-diaza-dodecane-2,11-diium dichloride methanol solvate.

In the title salt hydrate, C(22)H(30)N(2)O(6) (2+)·2Cl(-)·CH(4)O, the dication adopts a U-shaped conformation whereby the benzene rings are splayed out from the chain linking them. All components of the asymmetric unit are linked into a cohesive entity by a combination of O-H⋯Cl(-), N(+)-H⋯Cl(-) and N(+)-H⋯O charge-assisted hydrogen-bonding inter-actions. The assemblies thus formed are linked into supra-molecular helical chains along [010] via C-H⋯O contacts. The resulting chains are, in turn, consolidated into the three-dimensional crystal structure by C-H⋯π contacts.

Related literature

For related literature on dinucleating ligands, see: Fenton & Okawa (1997 ▶); Uhlenbrock & Krebs (1992 ▶); Ghiladi et al. (1997 ▶); Koga et al. (1998 ▶); Kitagawa et al. (2004 ▶); Bradshaw et al. (2005 ▶).

Experimental

Crystal data

C22H30N2O6 2+·2Cl−·CH4O

M = 521.42

Monoclinic,

a = 11.567 (3) Å

b = 11.352 (2) Å

c = 20.052 (5) Å

β = 102.760 (6)°

V = 2568.0 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 93 K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku AFC12κ/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.824, T max = 1.000

66801 measured reflections

5874 independent reflections

5598 reflections with I > 2σ(I)

R int = 0.050

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.05

5874 reflections

316 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrystalClear (Rigaku/MSC 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051824/hg2615sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051824/hg2615Isup2.hkl

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

C22H30N2O62+·2Cl−·CH4O	F(000) = 1104
Mr = 521.42	Dx = 1.349 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10052 reflections
a = 11.567 (3) Å	θ = 2.3–27.5°
b = 11.352 (2) Å	µ = 0.30 mm−1
c = 20.052 (5) Å	T = 93 K
β = 102.760 (6)°	Needle, pale-yellow
V = 2568.0 (10) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Rigaku AFC12κ/SATURN724 diffractometer	5874 independent reflections
Radiation source: fine-focus sealed tube	5598 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scans	θmax = 27.6°, θmin = 2.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −15→15
Tmin = 0.824, Tmax = 1.000	k = −14→14
66801 measured reflections	l = −25→23

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0485P)2 + 1.3403P] where P = (Fo2 + 2Fc2)/3
5874 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.51 e Å−3
3 restraints	Δρmin = −0.34 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.17035 (3)	0.90851 (3)	0.294477 (16)	0.02137 (9)
Cl2	0.38918 (3)	0.44293 (3)	0.645104 (15)	0.01982 (9)
O1	0.28564 (9)	0.80955 (8)	0.46826 (5)	0.0219 (2)
O2	0.31089 (9)	0.99194 (8)	0.43228 (5)	0.0226 (2)
H2O	0.2788	0.9626	0.3942	0.034*
O3	0.06032 (8)	0.70435 (9)	0.54842 (5)	0.0203 (2)
O4	−0.00828 (8)	0.63200 (8)	0.41190 (5)	0.01964 (19)
O5	0.29306 (9)	0.53733 (8)	0.47333 (5)	0.0206 (2)
O6	0.37621 (9)	0.36208 (8)	0.50329 (5)	0.0218 (2)
H6O	0.3793	0.3878	0.5429	0.033*
O7	−0.03491 (14)	1.03638 (17)	0.34730 (7)	0.0617 (5)
H7O	0.01604	1.0020	0.3302	0.093*
N1	0.29662 (9)	0.68943 (9)	0.58991 (5)	0.0149 (2)
H1A	0.2544	0.7080	0.5467	0.018*
H1B	0.3051	0.6088	0.5919	0.018*
N2	0.18404 (9)	0.65500 (9)	0.35526 (5)	0.0161 (2)
H2A	0.1871	0.6387	0.4006	0.019*
H2B	0.1845	0.7356	0.3507	0.019*
C1	0.32087 (11)	0.91027 (11)	0.48045 (6)	0.0168 (2)
C2	0.37852 (11)	0.95398 (11)	0.55001 (6)	0.0160 (2)
C3	0.39169 (12)	1.07574 (11)	0.56072 (7)	0.0197 (3)
H3	0.3632	1.1281	0.5238	0.024*
C4	0.44551 (12)	1.12139 (12)	0.62416 (7)	0.0212 (3)
H4	0.4538	1.2041	0.6306	0.025*
C5	0.48703 (11)	1.04508 (12)	0.67811 (7)	0.0188 (3)
H5	0.5249	1.0754	0.7216	0.023*
C6	0.47325 (11)	0.92430 (11)	0.66853 (6)	0.0169 (2)
H6	0.5010	0.8730	0.7061	0.020*
C7	0.41960 (10)	0.87617 (11)	0.60510 (6)	0.0149 (2)
C8	0.41731 (10)	0.74319 (11)	0.59949 (7)	0.0161 (2)
H8A	0.4519	0.7201	0.5604	0.019*
H8B	0.4684	0.7100	0.6415	0.019*
C9	0.22530 (11)	0.72536 (11)	0.63977 (6)	0.0180 (2)
H9A	0.2190	0.8123	0.6409	0.022*
H9B	0.2640	0.6977	0.6862	0.022*
C10	0.10344 (12)	0.67130 (12)	0.61791 (7)	0.0205 (3)
H10A	0.1081	0.5845	0.6223	0.025*
H10B	0.0504	0.7014	0.6466	0.025*
C11	−0.05474 (11)	0.65894 (13)	0.52063 (7)	0.0223 (3)
H11A	−0.1127	0.6933	0.5448	0.027*
H11B	−0.0550	0.5723	0.5264	0.027*
C12	−0.08839 (11)	0.68984 (13)	0.44601 (7)	0.0222 (3)
H12A	−0.1706	0.6641	0.4264	0.027*
H12B	−0.0840	0.7762	0.4401	0.027*
C13	−0.03062 (11)	0.66044 (12)	0.34123 (7)	0.0196 (3)
H13A	−0.0340	0.7469	0.3349	0.023*
H13B	−0.1072	0.6264	0.3170	0.023*
C14	0.06982 (11)	0.60919 (12)	0.31388 (7)	0.0191 (3)
H14A	0.0684	0.5222	0.3167	0.023*
H14B	0.0613	0.6317	0.2653	0.023*
C15	0.29383 (11)	0.60681 (11)	0.33720 (7)	0.0179 (2)
H15A	0.3636	0.6296	0.3731	0.022*
H15B	0.3030	0.6422	0.2936	0.022*
C16	0.29048 (10)	0.47434 (11)	0.33022 (6)	0.0155 (2)
C17	0.30167 (10)	0.39592 (11)	0.38574 (6)	0.0154 (2)
C18	0.29275 (11)	0.27445 (11)	0.37379 (7)	0.0175 (2)
H18	0.2987	0.2220	0.4113	0.021*
C19	0.27540 (11)	0.22952 (11)	0.30795 (7)	0.0190 (3)
H19	0.2671	0.1471	0.3003	0.023*
C20	0.27025 (11)	0.30619 (12)	0.25346 (7)	0.0196 (3)
H20	0.2629	0.2761	0.2085	0.023*
C21	0.27589 (11)	0.42735 (12)	0.26475 (7)	0.0185 (3)
H21	0.2696	0.4791	0.2269	0.022*
C22	0.32280 (10)	0.43990 (11)	0.45765 (6)	0.0160 (2)
C23	0.00444 (18)	1.02239 (16)	0.41719 (9)	0.0399 (4)
H23A	0.0692	1.0778	0.4342	0.060*
H23B	0.0330	0.9416	0.4271	0.060*
H23C	−0.0610	1.0378	0.4398	0.060*

	U11	U22	U33	U12	U13	U23
Cl1	0.03162 (17)	0.01666 (15)	0.01446 (16)	−0.00054 (11)	0.00213 (12)	0.00079 (11)
Cl2	0.02616 (16)	0.01604 (15)	0.01504 (16)	0.00147 (11)	−0.00022 (11)	0.00010 (10)
O1	0.0312 (5)	0.0167 (4)	0.0155 (5)	−0.0051 (4)	0.0004 (4)	−0.0002 (3)
O2	0.0343 (5)	0.0167 (4)	0.0139 (5)	−0.0046 (4)	−0.0007 (4)	0.0016 (3)
O3	0.0168 (4)	0.0256 (5)	0.0181 (5)	−0.0050 (4)	0.0034 (3)	−0.0004 (4)
O4	0.0181 (4)	0.0231 (5)	0.0173 (5)	0.0043 (4)	0.0031 (3)	0.0009 (4)
O5	0.0274 (5)	0.0173 (4)	0.0162 (5)	0.0042 (4)	0.0025 (4)	−0.0016 (3)
O6	0.0302 (5)	0.0199 (5)	0.0140 (5)	0.0071 (4)	0.0017 (4)	0.0008 (4)
O7	0.0603 (9)	0.0978 (12)	0.0255 (7)	0.0453 (9)	0.0063 (6)	0.0057 (7)
N1	0.0172 (5)	0.0135 (5)	0.0141 (5)	−0.0007 (4)	0.0032 (4)	−0.0008 (4)
N2	0.0188 (5)	0.0144 (5)	0.0143 (5)	0.0003 (4)	0.0020 (4)	−0.0008 (4)
C1	0.0175 (6)	0.0169 (6)	0.0158 (6)	−0.0002 (4)	0.0031 (5)	0.0012 (5)
C2	0.0162 (5)	0.0164 (6)	0.0148 (6)	−0.0006 (4)	0.0024 (4)	−0.0007 (4)
C3	0.0234 (6)	0.0162 (6)	0.0186 (7)	−0.0003 (5)	0.0024 (5)	0.0015 (5)
C4	0.0252 (6)	0.0156 (6)	0.0227 (7)	−0.0014 (5)	0.0048 (5)	−0.0034 (5)
C5	0.0188 (6)	0.0210 (6)	0.0162 (6)	−0.0015 (5)	0.0030 (5)	−0.0047 (5)
C6	0.0152 (5)	0.0206 (6)	0.0146 (6)	0.0010 (4)	0.0025 (4)	0.0001 (5)
C7	0.0138 (5)	0.0151 (5)	0.0161 (6)	0.0001 (4)	0.0038 (4)	−0.0009 (4)
C8	0.0149 (5)	0.0144 (5)	0.0183 (6)	0.0006 (4)	0.0026 (4)	0.0008 (4)
C9	0.0208 (6)	0.0199 (6)	0.0142 (6)	−0.0021 (5)	0.0057 (5)	−0.0023 (5)
C10	0.0224 (6)	0.0230 (6)	0.0169 (7)	−0.0047 (5)	0.0056 (5)	−0.0007 (5)
C11	0.0159 (6)	0.0287 (7)	0.0233 (7)	−0.0039 (5)	0.0066 (5)	−0.0048 (5)
C12	0.0155 (6)	0.0271 (7)	0.0237 (7)	0.0014 (5)	0.0041 (5)	−0.0045 (5)
C13	0.0195 (6)	0.0198 (6)	0.0173 (7)	0.0018 (5)	−0.0004 (5)	0.0009 (5)
C14	0.0200 (6)	0.0203 (6)	0.0153 (6)	−0.0011 (5)	0.0002 (5)	−0.0007 (5)
C15	0.0190 (6)	0.0160 (6)	0.0200 (7)	−0.0010 (4)	0.0068 (5)	0.0008 (5)
C16	0.0143 (5)	0.0160 (6)	0.0170 (6)	−0.0004 (4)	0.0051 (4)	−0.0004 (4)
C17	0.0131 (5)	0.0165 (6)	0.0165 (6)	−0.0002 (4)	0.0032 (4)	−0.0011 (5)
C18	0.0160 (5)	0.0158 (6)	0.0206 (7)	0.0005 (4)	0.0039 (5)	0.0006 (5)
C19	0.0156 (5)	0.0164 (6)	0.0245 (7)	−0.0010 (4)	0.0036 (5)	−0.0040 (5)
C20	0.0180 (6)	0.0236 (6)	0.0173 (6)	−0.0027 (5)	0.0042 (5)	−0.0059 (5)
C21	0.0188 (6)	0.0208 (6)	0.0166 (6)	−0.0017 (5)	0.0054 (5)	0.0007 (5)
C22	0.0144 (5)	0.0165 (6)	0.0169 (6)	0.0001 (4)	0.0030 (4)	0.0001 (4)
C23	0.0546 (11)	0.0366 (9)	0.0302 (9)	0.0102 (8)	0.0130 (8)	0.0026 (7)

O1—C1	1.2203 (16)	C8—H8B	0.9900
O2—C1	1.3254 (15)	C9—C10	1.5108 (18)
O2—H2O	0.8401	C9—H9A	0.9900
O3—C11	1.4212 (16)	C9—H9B	0.9900
O3—C10	1.4227 (17)	C10—H10A	0.9900
O4—C13	1.4203 (16)	C10—H10B	0.9900
O4—C12	1.4275 (16)	C11—C12	1.502 (2)
O5—C22	1.2200 (16)	C11—H11A	0.9900
O6—C22	1.3228 (15)	C11—H11B	0.9900
O6—H6O	0.8402	C12—H12A	0.9900
O7—C23	1.384 (2)	C12—H12B	0.9900
O7—H7O	0.8401	C13—C14	1.5068 (18)
N1—C9	1.4869 (16)	C13—H13A	0.9900
N1—C8	1.4965 (15)	C13—H13B	0.9900
N1—H1A	0.9200	C14—H14A	0.9900
N1—H1B	0.9200	C14—H14B	0.9900
N2—C14	1.4901 (16)	C15—C16	1.5100 (17)
N2—C15	1.4987 (16)	C15—H15A	0.9900
N2—H2A	0.9200	C15—H15B	0.9900
N2—H2B	0.9200	C16—C21	1.3924 (18)
C1—C2	1.4918 (17)	C16—C17	1.4090 (17)
C2—C3	1.4021 (17)	C17—C18	1.3996 (17)
C2—C7	1.4122 (17)	C17—C22	1.4941 (18)
C3—C4	1.3872 (19)	C18—C19	1.3880 (19)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.3864 (19)	C19—C20	1.3880 (19)
C4—H4	0.9500	C19—H19	0.9500
C5—C6	1.3889 (18)	C20—C21	1.3931 (18)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.3975 (18)	C21—H21	0.9500
C6—H6	0.9500	C23—H23A	0.9800
C7—C8	1.5136 (17)	C23—H23B	0.9800
C8—H8A	0.9900	C23—H23C	0.9800
C1—O2—H2O	109.5	O3—C11—H11A	110.0
C11—O3—C10	112.56 (10)	C12—C11—H11A	110.0
C13—O4—C12	112.29 (10)	O3—C11—H11B	110.0
C22—O6—H6O	109.7	C12—C11—H11B	110.0
C23—O7—H7O	104.8	H11A—C11—H11B	108.3
C9—N1—C8	116.24 (10)	O4—C12—C11	108.49 (11)
C9—N1—H1A	108.2	O4—C12—H12A	110.0
C8—N1—H1A	108.2	C11—C12—H12A	110.0
C9—N1—H1B	108.2	O4—C12—H12B	110.0
C8—N1—H1B	108.2	C11—C12—H12B	110.0
H1A—N1—H1B	107.4	H12A—C12—H12B	108.4
C14—N2—C15	115.62 (10)	O4—C13—C14	106.89 (10)
C14—N2—H2A	108.4	O4—C13—H13A	110.3
C15—N2—H2A	108.4	C14—C13—H13A	110.3
C14—N2—H2B	108.4	O4—C13—H13B	110.3
C15—N2—H2B	108.4	C14—C13—H13B	110.3
H2A—N2—H2B	107.4	H13A—C13—H13B	108.6
O1—C1—O2	122.54 (12)	N2—C14—C13	108.82 (10)
O1—C1—C2	124.02 (11)	N2—C14—H14A	109.9
O2—C1—C2	113.44 (11)	C13—C14—H14A	109.9
C3—C2—C7	119.37 (12)	N2—C14—H14B	109.9
C3—C2—C1	118.83 (11)	C13—C14—H14B	109.9
C7—C2—C1	121.80 (11)	H14A—C14—H14B	108.3
C4—C3—C2	121.36 (12)	N2—C15—C16	112.35 (10)
C4—C3—H3	119.3	N2—C15—H15A	109.1
C2—C3—H3	119.3	C16—C15—H15A	109.1
C5—C4—C3	119.35 (12)	N2—C15—H15B	109.1
C5—C4—H4	120.3	C16—C15—H15B	109.1
C3—C4—H4	120.3	H15A—C15—H15B	107.9
C4—C5—C6	119.97 (12)	C21—C16—C17	118.28 (11)
C4—C5—H5	120.0	C21—C16—C15	117.67 (11)
C6—C5—H5	120.0	C17—C16—C15	124.05 (11)
C5—C6—C7	121.75 (12)	C18—C17—C16	119.79 (12)
C5—C6—H6	119.1	C18—C17—C22	118.99 (11)
C7—C6—H6	119.1	C16—C17—C22	121.22 (11)
C6—C7—C2	118.20 (11)	C19—C18—C17	120.98 (12)
C6—C7—C8	117.04 (11)	C19—C18—H18	119.5
C2—C7—C8	124.64 (11)	C17—C18—H18	119.5
N1—C8—C7	114.63 (10)	C20—C19—C18	119.37 (12)
N1—C8—H8A	108.6	C20—C19—H19	120.3
C7—C8—H8A	108.6	C18—C19—H19	120.3
N1—C8—H8B	108.6	C19—C20—C21	119.93 (12)
C7—C8—H8B	108.6	C19—C20—H20	120.0
H8A—C8—H8B	107.6	C21—C20—H20	120.0
N1—C9—C10	108.30 (10)	C16—C21—C20	121.54 (12)
N1—C9—H9A	110.0	C16—C21—H21	119.2
C10—C9—H9A	110.0	C20—C21—H21	119.2
N1—C9—H9B	110.0	O5—C22—O6	122.85 (12)
C10—C9—H9B	110.0	O5—C22—C17	123.80 (11)
H9A—C9—H9B	108.4	O6—C22—C17	113.35 (11)
O3—C10—C9	106.25 (10)	O7—C23—H23A	109.5
O3—C10—H10A	110.5	O7—C23—H23B	109.5
C9—C10—H10A	110.5	H23A—C23—H23B	109.5
O3—C10—H10B	110.5	O7—C23—H23C	109.5
C9—C10—H10B	110.5	H23A—C23—H23C	109.5
H10A—C10—H10B	108.7	H23B—C23—H23C	109.5
O3—C11—C12	108.67 (11)
O1—C1—C2—C3	−166.11 (13)	O3—C11—C12—O4	63.74 (14)
O2—C1—C2—C3	13.74 (17)	C12—O4—C13—C14	171.72 (10)
O1—C1—C2—C7	13.7 (2)	C15—N2—C14—C13	176.57 (10)
O2—C1—C2—C7	−166.45 (11)	O4—C13—C14—N2	−55.46 (13)
C7—C2—C3—C4	0.7 (2)	C14—N2—C15—C16	−47.35 (15)
C1—C2—C3—C4	−179.44 (12)	N2—C15—C16—C21	108.39 (13)
C2—C3—C4—C5	−0.1 (2)	N2—C15—C16—C17	−71.88 (15)
C3—C4—C5—C6	−0.8 (2)	C21—C16—C17—C18	−2.78 (17)
C4—C5—C6—C7	0.94 (19)	C15—C16—C17—C18	177.49 (11)
C5—C6—C7—C2	−0.25 (18)	C21—C16—C17—C22	177.33 (11)
C5—C6—C7—C8	175.76 (11)	C15—C16—C17—C22	−2.41 (18)
C3—C2—C7—C6	−0.58 (18)	C16—C17—C18—C19	1.33 (18)
C1—C2—C7—C6	179.61 (11)	C22—C17—C18—C19	−178.77 (11)
C3—C2—C7—C8	−176.27 (12)	C17—C18—C19—C20	1.87 (18)
C1—C2—C7—C8	3.93 (19)	C18—C19—C20—C21	−3.56 (18)
C9—N1—C8—C7	−51.76 (14)	C17—C16—C21—C20	1.10 (18)
C6—C7—C8—N1	111.81 (12)	C15—C16—C21—C20	−179.15 (11)
C2—C7—C8—N1	−72.46 (15)	C19—C20—C21—C16	2.09 (19)
C8—N1—C9—C10	174.80 (10)	C18—C17—C22—O5	−154.04 (12)
C11—O3—C10—C9	179.84 (10)	C16—C17—C22—O5	25.86 (18)
N1—C9—C10—O3	−53.07 (13)	C18—C17—C22—O6	25.28 (16)
C10—O3—C11—C12	−175.41 (11)	C16—C17—C22—O6	−154.82 (11)
C13—O4—C12—C11	−177.50 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···Cl1	0.84	2.20	3.0316 (13)	170
O6—H6O···Cl2	0.84	2.12	2.9602 (13)	177
O7—H7O···Cl1	0.84	2.32	3.1586 (19)	174
N1—H1A···O1	0.92	2.05	2.7729 (16)	135
N1—H1A···O3	0.92	2.25	2.6809 (16)	108
N1—H1B···Cl2	0.92	2.27	3.1110 (13)	151
N2—H2A···O4	0.92	2.32	2.7245 (16)	106
N2—H2A···O5	0.92	2.04	2.7678 (16)	135
N2—H2B···Cl1	0.92	2.25	3.1157 (13)	156
C14—H14B···O7i	0.99	2.46	3.273 (2)	139
C8—H8B···Cgii	0.99	2.88	3.6364 (16)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯Cl1	0.84	2.20	3.0316 (13)	170
O6—H6O⋯Cl2	0.84	2.12	2.9602 (13)	177
O7—H7O⋯Cl1	0.84	2.32	3.1586 (19)	174
N1—H1A⋯O1	0.92	2.05	2.7729 (16)	135
N1—H1A⋯O3	0.92	2.25	2.6809 (16)	108
N1—H1B⋯Cl2	0.92	2.27	3.1110 (13)	151
N2—H2A⋯O4	0.92	2.32	2.7245 (16)	106
N2—H2A⋯O5	0.92	2.04	2.7678 (16)	135
N2—H2B⋯Cl1	0.92	2.25	3.1157 (13)	156
C14—H14B⋯O7i	0.99	2.46	3.273 (2)	139
C8—H8B⋯Cgii	0.99	2.88	3.6364 (16)	134

Symmetry codes: (i) ; (ii) . Cg is the centroid of the C16–C21 ring.