Hexa-kis-(3-chloro-2-methyl-anilinium) cyclo-hexa-phosphate dihydrate.

In the organic/inorganic salt hydrate, 6C7H9ClN(+)·P6O18 (6-)·2H2O, the cyclo-hexa-phosphate anion resides on an inversion centre. The asymmetric unit consists of three cations, one half-anion and a water mol-ecule. In the crystal, the water mol-ecules and the [P6O18](6-) anions are linked by O-H⋯O hydrogen bonds, generating infinite layers parallel to the ab plane. These layers are inter-connected by the organic cations through N-H⋯O hydrogen bonds.

Related literature

For the properties of hybrid materials, see: Shi et al. (2000 ▶); Yokotani et al. (1989 ▶); Xiao et al. (2005 ▶); Koo et al. (2004 ▶). For related structures containing cyclo­hexa­phosphate rings, see: Khedhiri et al. (2012 ▶); Amri et al. (2009 ▶); Marouani & Rzaigui (2010 ▶); Averbuch-Pouchot & Durif (1991 ▶). For bond lengths, see: Fábry et al. (2002 ▶). For the preparation of cyclo­hexa­phospho­ric acid, see: Schülke & Kayser (1985 ▶).

Experimental

Crystal data

6C7H9ClN+·P6O18 6−·2H2O

M = 1365.46

Triclinic,

a = 9.576 (5) Å

b = 10.187 (4) Å

c = 17.392 (5) Å

α = 94.48 (2)°

β = 103.74 (4)°

γ = 112.25 (4)°

V = 1498.5 (12) Å3

Z = 1

Mo Kα radiation

μ = 0.52 mm−1

T = 293 K

0.32 × 0.22 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

7464 measured reflections

7229 independent reflections

4800 reflections with I > 2σ(I)

R int = 0.033

2 standard reflections every 120 min intensity decay: 5%

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.128

S = 1.02

7229 reflections

405 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813033230/fj2652sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033230/fj2652Isup2.hkl

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

6C7H9ClN+·P6O186−·2H2O	Z = 1
Mr = 1365.46	F(000) = 704
Triclinic, P1	Dx = 1.513 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.576 (5) Å	Cell parameters from 25 reflections
b = 10.187 (4) Å	θ = 9–11°
c = 17.392 (5) Å	µ = 0.52 mm−1
α = 94.48 (2)°	T = 293 K
β = 103.74 (4)°	Prism, colorless
γ = 112.25 (4)°	0.32 × 0.22 × 0.15 mm
V = 1498.5 (12) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 28.0°, θmin = 2.2°
Graphite monochromator	h = −12→12
non–profiled ω scans	k = −13→13
7464 measured reflections	l = 0→22
7229 independent reflections	2 standard reflections every 120 min
4800 reflections with I > 2σ(I)	intensity decay: 5%

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.4583P] where P = (Fo2 + 2Fc2)/3
7229 reflections	(Δ/σ)max = 0.001
405 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.39 e Å−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
P1	0.10693 (8)	0.76984 (7)	0.50600 (4)	0.0233 (2)
P2	0.32227 (7)	0.62757 (7)	0.52138 (4)	0.0217 (2)
P3	0.13627 (8)	0.34633 (7)	0.41193 (4)	0.0236 (2)
O1	0.2396 (2)	0.9092 (2)	0.54611 (13)	0.0389 (7)
O2	−0.0196 (2)	0.7621 (2)	0.43465 (12)	0.0320 (6)
O3	0.1712 (2)	0.6560 (2)	0.47796 (11)	0.0302 (6)
O4	0.3518 (2)	0.6539 (2)	0.61045 (11)	0.0301 (6)
O5	0.4520 (2)	0.7054 (2)	0.48872 (13)	0.0363 (7)
O6	0.2550 (2)	0.4574 (2)	0.49312 (12)	0.0333 (6)
O7	0.1293 (2)	0.4211 (2)	0.34254 (12)	0.0329 (6)
O8	0.1743 (2)	0.2189 (2)	0.41061 (12)	0.0343 (6)
O9	0.0321 (2)	0.6948 (2)	0.57240 (12)	0.0327 (6)
Cl1	0.34937 (16)	−0.02530 (14)	0.04005 (7)	0.0821 (5)
N1	0.3436 (3)	0.1365 (3)	0.32844 (15)	0.0306 (8)
C1	0.2839 (3)	0.1210 (3)	0.24115 (17)	0.0308 (8)
C2	0.3467 (4)	0.0618 (3)	0.19071 (19)	0.0375 (10)
C3	0.2856 (4)	0.0540 (4)	0.1089 (2)	0.0483 (11)
C4	0.1740 (5)	0.1046 (4)	0.0786 (2)	0.0564 (11)
C5	0.1155 (4)	0.1631 (4)	0.1303 (2)	0.0560 (14)
C6	0.1694 (4)	0.1698 (3)	0.21233 (19)	0.0416 (10)
C7	0.4738 (5)	0.0117 (4)	0.2232 (2)	0.0579 (16)
Cl2	0.6890 (2)	0.81050 (16)	0.11837 (7)	0.1000 (6)
N2	0.7057 (3)	0.8023 (3)	0.41707 (15)	0.0281 (8)
C8	0.6282 (3)	0.7400 (3)	0.33153 (17)	0.0292 (8)
C9	0.6979 (4)	0.8032 (3)	0.27466 (18)	0.0359 (10)
C10	0.6160 (5)	0.7370 (4)	0.1948 (2)	0.0546 (13)
C11	0.4744 (6)	0.6175 (5)	0.1737 (3)	0.0785 (18)
C12	0.4108 (5)	0.5590 (5)	0.2319 (3)	0.0726 (17)
C13	0.4874 (4)	0.6200 (4)	0.3115 (2)	0.0464 (11)
C14	0.8500 (4)	0.9359 (4)	0.2981 (2)	0.0518 (12)
Cl3	1.0171 (2)	0.67872 (17)	0.06613 (8)	0.1091 (7)
N3	0.8848 (3)	0.5080 (3)	0.32105 (15)	0.0317 (8)
C15	0.8371 (3)	0.4984 (3)	0.23430 (18)	0.0345 (9)
C16	0.9415 (4)	0.5911 (3)	0.19903 (19)	0.0403 (10)
C17	0.8953 (5)	0.5702 (4)	0.1164 (2)	0.0641 (14)
C18	0.7528 (7)	0.4644 (6)	0.0704 (3)	0.109 (2)
C19	0.6514 (6)	0.3770 (6)	0.1070 (3)	0.105 (2)
C20	0.6930 (4)	0.3946 (4)	0.1898 (2)	0.0662 (12)
C21	1.0981 (4)	0.7057 (4)	0.2497 (3)	0.0616 (14)
O1W	0.5687 (3)	0.0657 (3)	0.59977 (17)	0.0498 (9)
H1A	0.284 (4)	0.166 (4)	0.357 (2)	0.056 (11)*
H1B	0.350 (4)	0.050 (4)	0.346 (2)	0.049 (10)*
H1C	0.446 (4)	0.210 (4)	0.3448 (19)	0.039 (9)*
H4	0.13811	0.09937	0.02333	0.0851*
H5	0.03996	0.19805	0.11032	0.0839*
H6	0.12852	0.20698	0.24769	0.0624*
H7A	0.49965	0.02657	0.28092	0.0874*
H7B	0.43730	−0.08912	0.20193	0.0874*
H7C	0.56571	0.06563	0.20757	0.0874*
H2A	0.640 (4)	0.755 (4)	0.445 (2)	0.047 (10)*
H2B	0.797 (5)	0.786 (4)	0.431 (2)	0.059 (11)*
H2C	0.726 (4)	0.896 (4)	0.427 (2)	0.043 (9)*
H11	0.42203	0.57662	0.11971	0.1168*
H12	0.31566	0.47788	0.21759	0.1088*
H13	0.44471	0.58085	0.35145	0.0694*
H14A	0.88732	0.96426	0.35569	0.0779*
H14B	0.92709	0.91552	0.27887	0.0779*
H14C	0.83286	1.01277	0.27464	0.0779*
H3A	0.979 (5)	0.484 (5)	0.334 (3)	0.089 (15)*
H3B	0.802 (5)	0.442 (4)	0.344 (2)	0.066 (12)*
H3C	0.912 (4)	0.591 (4)	0.348 (2)	0.058 (12)*
H18	0.72554	0.45254	0.01451	0.1635*
H19	0.55476	0.30596	0.07609	0.1573*
H20	0.62411	0.33662	0.21526	0.0991*
H21A	1.10761	0.70244	0.30568	0.0919*
H21B	1.18180	0.68856	0.23587	0.0919*
H21C	1.10459	0.79895	0.23990	0.0919*
H1W	0.476 (6)	0.015 (5)	0.576 (3)	0.085 (17)*
H2W	0.583 (5)	0.135 (5)	0.577 (3)	0.083 (16)*

	U11	U22	U33	U12	U13	U23
P1	0.0201 (3)	0.0222 (3)	0.0295 (4)	0.0093 (3)	0.0095 (3)	0.0054 (3)
P2	0.0176 (3)	0.0215 (3)	0.0254 (4)	0.0070 (3)	0.0073 (3)	0.0033 (3)
P3	0.0206 (3)	0.0227 (3)	0.0275 (4)	0.0079 (3)	0.0090 (3)	0.0033 (3)
O1	0.0334 (11)	0.0220 (10)	0.0539 (14)	0.0051 (9)	0.0112 (10)	0.0025 (9)
O2	0.0303 (10)	0.0385 (11)	0.0341 (11)	0.0197 (9)	0.0102 (9)	0.0125 (9)
O3	0.0270 (10)	0.0348 (11)	0.0308 (10)	0.0192 (9)	0.0038 (8)	−0.0019 (8)
O4	0.0260 (10)	0.0332 (10)	0.0258 (10)	0.0085 (8)	0.0053 (8)	0.0021 (8)
O5	0.0253 (10)	0.0401 (12)	0.0422 (12)	0.0070 (9)	0.0173 (9)	0.0110 (10)
O6	0.0344 (11)	0.0223 (10)	0.0355 (11)	0.0100 (9)	0.0005 (9)	0.0018 (8)
O7	0.0339 (11)	0.0351 (11)	0.0329 (11)	0.0134 (9)	0.0153 (9)	0.0102 (9)
O8	0.0363 (11)	0.0281 (10)	0.0425 (12)	0.0163 (9)	0.0142 (9)	0.0032 (9)
O9	0.0232 (9)	0.0468 (12)	0.0355 (11)	0.0167 (9)	0.0146 (8)	0.0169 (9)
Cl1	0.1113 (10)	0.0872 (8)	0.0560 (6)	0.0345 (7)	0.0527 (7)	0.0022 (6)
N1	0.0265 (13)	0.0326 (14)	0.0310 (13)	0.0116 (11)	0.0078 (10)	0.0014 (11)
C1	0.0283 (14)	0.0289 (14)	0.0277 (14)	0.0048 (12)	0.0073 (12)	0.0018 (12)
C2	0.0372 (16)	0.0324 (16)	0.0406 (18)	0.0076 (13)	0.0194 (14)	0.0029 (13)
C3	0.055 (2)	0.0407 (19)	0.0402 (19)	0.0060 (16)	0.0233 (17)	−0.0002 (15)
C4	0.057 (2)	0.066 (2)	0.0317 (18)	0.013 (2)	0.0083 (17)	0.0068 (17)
C5	0.046 (2)	0.070 (3)	0.044 (2)	0.0226 (19)	0.0013 (17)	0.0090 (18)
C6	0.0369 (17)	0.0464 (19)	0.0375 (18)	0.0168 (15)	0.0061 (14)	0.0010 (14)
C7	0.065 (2)	0.068 (3)	0.068 (3)	0.042 (2)	0.040 (2)	0.023 (2)
Cl2	0.1609 (14)	0.1171 (11)	0.0480 (6)	0.0661 (10)	0.0541 (8)	0.0379 (7)
N2	0.0295 (13)	0.0284 (13)	0.0300 (13)	0.0137 (11)	0.0109 (11)	0.0083 (10)
C8	0.0295 (14)	0.0285 (14)	0.0311 (15)	0.0142 (12)	0.0078 (12)	0.0051 (12)
C9	0.0436 (17)	0.0363 (16)	0.0364 (17)	0.0218 (14)	0.0167 (14)	0.0103 (13)
C10	0.078 (3)	0.063 (2)	0.0319 (18)	0.035 (2)	0.0210 (18)	0.0123 (17)
C11	0.094 (4)	0.076 (3)	0.039 (2)	0.025 (3)	−0.005 (2)	−0.010 (2)
C12	0.062 (3)	0.058 (3)	0.057 (3)	−0.002 (2)	−0.004 (2)	−0.011 (2)
C13	0.0406 (18)	0.0370 (18)	0.050 (2)	0.0044 (15)	0.0136 (16)	0.0016 (15)
C14	0.051 (2)	0.047 (2)	0.062 (2)	0.0133 (17)	0.0319 (18)	0.0225 (18)
Cl3	0.1496 (14)	0.1094 (11)	0.0706 (8)	0.0299 (10)	0.0648 (9)	0.0485 (8)
N3	0.0322 (14)	0.0333 (14)	0.0278 (13)	0.0114 (12)	0.0081 (11)	0.0076 (11)
C15	0.0356 (16)	0.0332 (16)	0.0313 (15)	0.0114 (13)	0.0074 (13)	0.0090 (12)
C16	0.0448 (18)	0.0356 (17)	0.0379 (17)	0.0138 (14)	0.0111 (15)	0.0092 (14)
C17	0.080 (3)	0.059 (2)	0.040 (2)	0.011 (2)	0.020 (2)	0.0190 (18)
C18	0.126 (5)	0.109 (4)	0.033 (2)	−0.002 (4)	0.002 (3)	0.012 (3)
C19	0.086 (4)	0.101 (4)	0.050 (3)	−0.022 (3)	−0.015 (3)	0.001 (3)
C20	0.050 (2)	0.061 (2)	0.049 (2)	−0.0095 (19)	−0.0008 (18)	0.0114 (19)
C21	0.050 (2)	0.051 (2)	0.068 (3)	−0.0003 (18)	0.022 (2)	0.017 (2)
O1W	0.0428 (15)	0.0427 (14)	0.0590 (16)	0.0150 (12)	0.0074 (13)	0.0182 (13)

Cl1—C3	1.741 (4)	C4—C5	1.373 (6)
Cl2—C10	1.737 (4)	C5—C6	1.384 (5)
Cl3—C17	1.734 (5)	C4—H4	0.9300
P1—O2	1.487 (2)	C5—H5	0.9300
P1—O9	1.596 (2)	C6—H6	0.9300
P1—O3	1.599 (2)	C7—H7C	0.9600
P1—O1	1.475 (2)	C7—H7B	0.9600
P2—O5	1.468 (2)	C7—H7A	0.9600
P2—O3	1.606 (2)	C8—C9	1.388 (4)
P2—O4	1.490 (2)	C8—C13	1.377 (5)
P2—O6	1.591 (2)	C9—C14	1.502 (5)
P3—O9i	1.601 (2)	C9—C10	1.391 (5)
P3—O7	1.478 (2)	C10—C11	1.378 (7)
P3—O8	1.475 (2)	C11—C12	1.365 (7)
P3—O6	1.606 (2)	C12—C13	1.371 (6)
O1W—H1W	0.82 (5)	C11—H11	0.9300
O1W—H2W	0.82 (5)	C12—H12	0.9300
N1—C1	1.462 (4)	C13—H13	0.9300
N1—H1C	0.94 (4)	C14—H14C	0.9600
N1—H1B	0.97 (4)	C14—H14A	0.9600
N1—H1A	0.95 (4)	C14—H14B	0.9600
N2—C8	1.462 (4)	C15—C16	1.391 (5)
N2—H2B	0.93 (5)	C15—C20	1.372 (5)
N2—H2A	0.90 (4)	C16—C21	1.508 (6)
N2—H2C	0.89 (4)	C16—C17	1.373 (5)
N3—C15	1.453 (4)	C17—C18	1.377 (7)
N3—H3C	0.85 (4)	C18—C19	1.367 (8)
N3—H3B	1.01 (4)	C19—C20	1.378 (6)
N3—H3A	1.00 (5)	C18—H18	0.9300
C1—C6	1.375 (5)	C19—H19	0.9300
C1—C2	1.392 (5)	C20—H20	0.9300
C2—C7	1.500 (6)	C21—H21C	0.9600
C2—C3	1.387 (5)	C21—H21A	0.9600
C3—C4	1.370 (6)	C21—H21B	0.9600
O1—P1—O2	120.42 (13)	C5—C6—H6	120.00
O1—P1—O3	110.23 (13)	C1—C6—H6	120.00
O1—P1—O9	108.66 (12)	C2—C7—H7C	109.00
O2—P1—O3	105.54 (12)	C2—C7—H7A	109.00
O2—P1—O9	110.27 (13)	C2—C7—H7B	109.00
O3—P1—O9	99.71 (11)	H7A—C7—H7B	109.00
O3—P2—O4	110.07 (12)	H7A—C7—H7C	109.00
O3—P2—O5	108.64 (12)	H7B—C7—H7C	109.00
O3—P2—O6	100.22 (12)	N2—C8—C13	117.5 (3)
O4—P2—O5	118.09 (13)	C9—C8—C13	123.1 (3)
O4—P2—O6	106.34 (12)	N2—C8—C9	119.4 (3)
O5—P2—O6	112.00 (12)	C10—C9—C14	122.5 (3)
O6—P3—O7	110.89 (12)	C8—C9—C14	122.0 (3)
O6—P3—O8	106.05 (12)	C8—C9—C10	115.5 (3)
O6—P3—O9i	102.62 (12)	Cl2—C10—C9	119.5 (3)
O7—P3—O8	121.53 (13)	C9—C10—C11	122.1 (4)
O7—P3—O9i	104.67 (12)	Cl2—C10—C11	118.4 (3)
O8—P3—O9i	109.53 (12)	C10—C11—C12	120.2 (4)
P1—O3—P2	130.72 (13)	C11—C12—C13	119.9 (5)
P2—O6—P3	134.20 (14)	C8—C13—C12	119.2 (4)
P1—O9—P3i	133.29 (14)	C12—C11—H11	120.00
H1W—O1W—H2W	101 (5)	C10—C11—H11	120.00
H1A—N1—H1B	108 (3)	C13—C12—H12	120.00
H1A—N1—H1C	107 (3)	C11—C12—H12	120.00
C1—N1—H1B	114 (2)	C8—C13—H13	120.00
C1—N1—H1C	107 (2)	C12—C13—H13	120.00
H1B—N1—H1C	108 (3)	C9—C14—H14C	109.00
C1—N1—H1A	113 (2)	C9—C14—H14B	109.00
H2B—N2—H2C	112 (4)	H14A—C14—H14C	109.00
H2A—N2—H2B	110 (3)	C9—C14—H14A	109.00
H2A—N2—H2C	109 (4)	H14A—C14—H14B	109.00
C8—N2—H2A	108 (2)	H14B—C14—H14C	109.00
C8—N2—H2B	107 (2)	C16—C15—C20	122.3 (3)
C8—N2—H2C	111 (2)	N3—C15—C16	118.9 (3)
C15—N3—H3B	116 (2)	N3—C15—C20	118.8 (3)
H3B—N3—H3C	104 (3)	C15—C16—C21	121.1 (3)
C15—N3—H3C	114 (2)	C17—C16—C21	122.5 (4)
C15—N3—H3A	107 (3)	C15—C16—C17	116.4 (3)
H3A—N3—H3C	107 (4)	Cl3—C17—C18	117.5 (3)
H3A—N3—H3B	109 (4)	C16—C17—C18	122.2 (4)
C2—C1—C6	122.5 (3)	Cl3—C17—C16	120.3 (3)
N1—C1—C6	117.9 (3)	C17—C18—C19	119.9 (5)
N1—C1—C2	119.6 (3)	C18—C19—C20	119.7 (5)
C3—C2—C7	122.4 (3)	C15—C20—C19	119.3 (4)
C1—C2—C7	121.9 (3)	C17—C18—H18	120.00
C1—C2—C3	115.7 (3)	C19—C18—H18	120.00
Cl1—C3—C2	119.6 (3)	C20—C19—H19	120.00
C2—C3—C4	123.0 (4)	C18—C19—H19	120.00
Cl1—C3—C4	117.4 (3)	C15—C20—H20	120.00
C3—C4—C5	119.6 (3)	C19—C20—H20	120.00
C4—C5—C6	119.7 (4)	C16—C21—H21B	109.00
C1—C6—C5	119.5 (3)	C16—C21—H21C	109.00
C5—C4—H4	120.00	C16—C21—H21A	109.00
C3—C4—H4	120.00	H21A—C21—H21C	109.00
C4—C5—H5	120.00	H21B—C21—H21C	110.00
C6—C5—H5	120.00	H21A—C21—H21B	109.00
O1—P1—O3—P2	38.7 (2)	C3—C4—C5—C6	−0.3 (6)
O2—P1—O3—P2	170.22 (16)	C4—C5—C6—C1	1.6 (5)
O9—P1—O3—P2	−75.42 (19)	N2—C8—C9—C10	−179.9 (3)
O2—P1—O9—P3i	−19.0 (2)	N2—C8—C9—C14	−1.1 (5)
O3—P1—O9—P3i	−129.62 (18)	C13—C8—C9—C10	−0.1 (5)
O1—P1—O9—P3i	115.04 (19)	C13—C8—C9—C14	178.7 (4)
O4—P2—O3—P1	33.9 (2)	N2—C8—C13—C12	179.7 (4)
O5—P2—O3—P1	−96.79 (18)	C9—C8—C13—C12	−0.2 (6)
O5—P2—O6—P3	−79.6 (2)	C8—C9—C10—Cl2	177.9 (3)
O6—P2—O3—P1	145.66 (17)	C8—C9—C10—C11	0.6 (6)
O3—P2—O6—P3	35.4 (2)	C14—C9—C10—Cl2	−1.0 (6)
O4—P2—O6—P3	150.01 (19)	C14—C9—C10—C11	−178.3 (4)
O7—P3—O6—P2	22.7 (2)	Cl2—C10—C11—C12	−178.1 (4)
O8—P3—O6—P2	156.50 (19)	C9—C10—C11—C12	−0.8 (8)
O9i—P3—O6—P2	−88.6 (2)	C10—C11—C12—C13	0.5 (8)
O6i—P3i—O9—P1	61.0 (2)	C11—C12—C13—C8	−0.1 (7)
O7i—P3i—O9—P1	176.90 (17)	N3—C15—C16—C17	175.3 (3)
O8i—P3i—O9—P1	−51.3 (2)	N3—C15—C16—C21	−3.4 (5)
N1—C1—C2—C3	−178.7 (3)	C20—C15—C16—C17	−2.3 (5)
N1—C1—C2—C7	0.6 (5)	C20—C15—C16—C21	179.0 (4)
C6—C1—C2—C3	−0.4 (5)	N3—C15—C20—C19	−175.0 (4)
C6—C1—C2—C7	178.8 (3)	C16—C15—C20—C19	2.5 (6)
N1—C1—C6—C5	177.0 (3)	C15—C16—C17—Cl3	−179.5 (3)
C2—C1—C6—C5	−1.3 (5)	C15—C16—C17—C18	0.6 (7)
C1—C2—C3—Cl1	−177.2 (3)	C21—C16—C17—Cl3	−0.8 (6)
C1—C2—C3—C4	1.9 (5)	C21—C16—C17—C18	179.3 (5)
C7—C2—C3—Cl1	3.6 (5)	Cl3—C17—C18—C19	−179.2 (5)
C7—C2—C3—C4	−177.3 (4)	C16—C17—C18—C19	0.7 (9)
Cl1—C3—C4—C5	177.5 (3)	C17—C18—C19—C20	−0.5 (9)
C2—C3—C4—C5	−1.6 (6)	C18—C19—C20—C15	−1.0 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O8	0.95 (4)	1.76 (4)	2.705 (4)	179 (5)
N1—H1B···O1Wii	0.97 (4)	1.85 (4)	2.779 (4)	160 (3)
N1—H1C···O4iii	0.94 (4)	1.83 (4)	2.766 (4)	173 (3)
O1W—H1W···O1iv	0.82 (5)	2.02 (6)	2.813 (4)	164 (5)
O1W—H2W···O5iii	0.82 (5)	2.14 (5)	2.934 (4)	163 (5)
N2—H2A···O5	0.90 (4)	2.02 (4)	2.871 (4)	156 (4)
N2—H2B···O2v	0.93 (5)	1.85 (5)	2.763 (4)	166 (3)
N2—H2C···O1vi	0.89 (4)	1.89 (4)	2.775 (4)	176 (4)
N3—H3A···O7v	1.00 (5)	1.77 (5)	2.759 (4)	171 (5)
N3—H3B···O4iii	1.01 (4)	1.83 (4)	2.834 (4)	172 (4)
N3—H3C···O2v	0.85 (4)	2.00 (4)	2.827 (4)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O8	0.95 (4)	1.76 (4)	2.705 (4)	179 (5)
N1—H1B⋯O1W i	0.97 (4)	1.85 (4)	2.779 (4)	160 (3)
N1—H1C⋯O4ii	0.94 (4)	1.83 (4)	2.766 (4)	173 (3)
O1W—H1W⋯O1iii	0.82 (5)	2.02 (6)	2.813 (4)	164 (5)
O1W—H2W⋯O5ii	0.82 (5)	2.14 (5)	2.934 (4)	163 (5)
N2—H2A⋯O5	0.90 (4)	2.02 (4)	2.871 (4)	156 (4)
N2—H2B⋯O2iv	0.93 (5)	1.85 (5)	2.763 (4)	166 (3)
N2—H2C⋯O1v	0.89 (4)	1.89 (4)	2.775 (4)	176 (4)
N3—H3A⋯O7iv	1.00 (5)	1.77 (5)	2.759 (4)	171 (5)
N3—H3B⋯O4ii	1.01 (4)	1.83 (4)	2.834 (4)	172 (4)
N3—H3C⋯O2iv	0.85 (4)	2.00 (4)	2.827 (4)	166 (3)

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