Tris(2-ammonio­ethyl)­amine benzene-1,3,5-tri­carboxyl­ate 5.5-hydrate

The structure of the title compound, 2,2',2''-nitrilo­tri­(ethyl­ammonium) benzene-1,3,5-tri­carboxyl­ate 5.5-hydrate, C₆H₂₁N₄³⁺·C₉H₃O₆^3-·5.5H₂O, comprises the 1:1 organic salt of tris(2-ammonio­ethyl)­amine and benzene-1,3,5-tri­carboxyl­ate in a complex hydrogen-bonded network which also includes four full water mol­ecules and two with partial occupancies of 0.80 (2) and 0.70 (2).

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• H-atom completeness 98%
• Disorder in solvent or counterion
• R factor = 0.063
• wR factor = 0.208
• Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



DIFMX_01  Alert C The maximum difference density is > 0.1*ZMAX*0.75
          _refine_diff_density_max given =      0.678
          Test value =      0.600

DIFMX_02  Alert C The minimum difference density is > 0.1*ZMAX*0.75
          The relevant atom site should be identified.

PLAT_302  Alert C Anion/Solvent Disorder .........................      25.00 Perc.

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C15 H35 N4 O11.5
          Atom count from the _atom_site data:  C15 H34.3 N4 O11.5

CELLZ_01
         From the CIF: _cell_formula_units_Z    2
         From the CIF: _chemical_formula_sum  C15 H35 N4 O11.50
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C         30.00     30.00    0.00
         H         70.00     68.60    1.40
         N          8.00      8.00    0.00
         O         23.00     23.00    0.00
          Difference between formula and atom_site contents detected.
          WARNING: H atoms missing from atom site list. Is this intentional?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

---

S1. Comment

A search of the April 2003 release of the Cambridge Structural Database (Allen, 2002) reveals that both benzene-1,3,5-tricarboxylic acid and cyclohexane-1,3,5-tricarboxylic acid are involved in the structures of 61 salt, adduct, clatherate or hydrate complexes. Of these structures, 17 incorporate molecules that do not contain either an amine group or heterocyclic N atom whereas the remaining structures do contain other molecules with these features. Of the latter structures, only five comprise molecules with three or more N atoms, available for protonation from the acid H atoms, in the same molecule. Three of these are large selective tripod molecules (Ballester et al., 1997, 2001), while the other two are derivatives of 1,4,8,11-tetraazacyclotetradecane (Burchell et al., 2001) and 1,3,5-triaminocyclohexane (Menger et al., 2002). Interestingly, the structures of either tricarboxylic acid analogue with tris(2-aminoethyl)amine have not been determined. Separate mixing of the two triacids with tris(2-aminoethyl)amine resulted in crystals and subsequent determination of the structure of the organic salt of just the benzene analogue with the tripod amine.

The 1:1 organic salt, (I), of benzene-1,3,5-tricarboxylate with tris(2-ammonioethyl)amine consists of both molecules in a complex hydrogen-bonded network which also includes four water molecules and two partial occupancy water molecules (Fig. 1). Two of the base ammonium groups (N4A and N7A) associate through all their H atoms to different carboxylate O atoms (except for N4A—H43A···O5w), while the third ammonium group (N10A) associates through two of its H atoms to three of the water molecules (O1w, O2w and O6w), while the third H atom (H11A) associates to O52B. Of the water molecules, O1w–O4w mostly associate to carboxylate O atoms (O3w—H31 and O4w—H41 associate to O6w) whereas O5w and O6w associate to other water molecules, although O6w is 2.916 (3) Å from N10A(1 − x, 1 − y, 1 − z). Partial occupancies for O5w (0.80 occupancy) and O6w (0.70 occupancy), giving a total of 5.5 waters, best fits the CHN analysis of the crystals (found: C 39.3, H 7.6, N 12.4%; C₁₅H₃₅N₄O_11.5 requires C 39.6, H 7.7, N 12.3%). Residual electron density of 0.68 e Å⁻³ was located 1.01 Å from O2w and is essentially equidistant from the two H atoms creating H—O2w peak angles of 46–47°. The first four unassigned peaks in the difference map closely proximate O1w–O4w and their respective H atoms but are not in suitable positions to be considered as alternative H atoms.

S2. Experimental

Equimolar amounts of benzene-1,3,5-tricarboxylic acid and tris(2-aminoethyl)amine were refluxed in ethanol for 20 min. Total evaporation of the solvent gave colourless prisms (m.p. 453 K).

S3. Refinement

All H atoms on the amines were initially located in difference syntheses but were then included in the refinement (along with all non-water H atoms), at calculated positions, as riding models with N—H set to 0.89 Å and C—H set to 0.97 Å (CH₂) and 0.93 Å (Ar—H) and the isotropic displacement parameters were allowed to refine. All water H atoms, except H31, H41, H61 and H62, were then located in difference syntheses and positional parameters were refined while the isotropic displacement parameters were set equal to 1.25U_eq of the preceeding normal atom. Atoms H31, H41, H61 and H62 were included at calculated positions and positional parameters refined while the isotropic displacement parameters were set equal to 1.25U_eq of the preceeding normal atom. No suitable position for H62 could be located without causing intermolecular H62···H distances of < 2.0 Å.

Computing details

Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: Xtal3.2 (Hall et al., 1992); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The molecular configuration and atom-numbering scheme for the title compound, showing 50% probability displacement parameters.

2,2',2''-Nitrilotri(ethylammonium) benzene-1,3,5-tricarboxylate 5.5-hydrate

Crystal data

C6H21N4^3+·C9H3O6^3^−·5.5H2O	F(000) = 490
Mr = 455.47	Dx = 1.355 Mg m^−3
Triclinic, P1	Melting point: 453 K K
a = 9.585 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.711 (1) Å	Cell parameters from 25 reflections
c = 12.980 (2) Å	θ = 6–14°
α = 72.79 (1)°	µ = 0.12 mm^−1
β = 73.67 (1)°	T = 298 K
γ = 62.93 (8)°	Prism, colourless
V = 1116.5 (8) Å^3	0.60 × 0.50 × 0.50 mm
Z = 2

Data collection

Enraf-Nonius CAD-4 diffractometer	2940 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
2θ/ω scans	h = 0→11
Absorption correction: ψ scan (Xtal3.2; Hall et al., 1992)	k = −11→12
Tmin = 0.930, Tmax = 0.942	l = −14→15
4196 measured reflections	3 standard reflections every 200 reflections
3937 independent reflections	intensity decay: 25%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ^2(Fo^2) + (0.127P)^2 + 0.3227P] where P = (Fo^2 + 2Fc^2)/3
3937 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.68 e Å^−3
0 restraints	Δρmin = −0.50 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.1266 (3)	0.5040 (2)	0.23580 (17)	0.0301 (5)
C2A	0.1778 (3)	0.3546 (3)	0.2953 (2)	0.0355 (6)
H21A	0.1034	0.3172	0.2938	0.046 (9)*
H22A	0.1751	0.3517	0.3712	0.031 (7)*
C3A	0.3427 (3)	0.2606 (3)	0.2474 (2)	0.0376 (7)
H31A	0.3646	0.1615	0.2820	0.052 (9)*
H32A	0.3490	0.2704	0.1697	0.036 (8)*
N4A	0.4638 (3)	0.2996 (3)	0.26388 (19)	0.0372 (6)
H41A	0.4637	0.2836	0.3352	0.054 (10)*
H42A	0.4408	0.3918	0.2353	0.053 (10)*
H43A	0.5594	0.2469	0.2310	0.035 (8)*
C5A	0.0737 (3)	0.5213 (3)	0.1345 (2)	0.0370 (7)
H51A	−0.0358	0.5316	0.1516	0.052 (9)*
H52A	0.1384	0.4361	0.1034	0.031 (7)*
C6A	0.0860 (4)	0.6502 (3)	0.0511 (2)	0.0404 (7)
H61A	0.0513	0.6579	−0.0147	0.049 (9)*
H62A	0.0171	0.7362	0.0803	0.049 (9)*
N7A	0.2519 (3)	0.6374 (2)	0.02381 (18)	0.0337 (5)
H71A	0.2851	0.6265	0.0847	0.052 (10)*
H72A	0.2565	0.7162	−0.0223	0.043 (9)*
H73A	0.3140	0.5619	−0.0074	0.035 (8)*
C8A	−0.0004 (3)	0.5986 (3)	0.3064 (2)	0.0378 (7)
H81A	−0.0762	0.5564	0.3443	0.048 (9)*
H82A	−0.0560	0.6894	0.2612	0.031 (7)*
C9A	0.0601 (4)	0.6253 (3)	0.3899 (2)	0.0430 (7)
H91A	−0.0297	0.6763	0.4407	0.056 (10)*
H92A	0.1234	0.5343	0.4312	0.040 (8)*
N10A	0.1576 (3)	0.7091 (3)	0.3383 (2)	0.0435 (6)
H11A	0.2445	0.6593	0.2959	0.050 (9)*
H12A	0.1857	0.7275	0.3901	0.046 (9)*
H13A	0.1014	0.7910	0.2979	0.055 (10)*
C1B	0.4084 (3)	0.2055 (3)	0.6652 (2)	0.0289 (6)
C11B	0.4038 (3)	0.2376 (3)	0.5447 (2)	0.0361 (6)
O11B	0.4415 (3)	0.3378 (3)	0.48424 (17)	0.0571 (7)
O12B	0.3571 (4)	0.1696 (3)	0.51031 (18)	0.0614 (7)
C2B	0.3635 (3)	0.0985 (3)	0.7357 (2)	0.0285 (6)
H2B	0.3399	0.0417	0.7071	0.028 (7)*
C3B	0.3534 (3)	0.0754 (3)	0.8479 (2)	0.0272 (6)
C31B	0.2961 (3)	−0.0363 (3)	0.9230 (2)	0.0298 (6)
O31B	0.2836 (2)	−0.12126 (19)	0.87925 (15)	0.0352 (5)
O32B	0.2610 (3)	−0.0369 (2)	1.02305 (16)	0.0447 (5)
C4B	0.3878 (3)	0.1603 (3)	0.8908 (2)	0.0290 (6)
H4B	0.3769	0.1478	0.9662	0.040 (8)*
C5B	0.4384 (3)	0.2640 (3)	0.8215 (2)	0.0272 (6)
C51B	0.4750 (3)	0.3564 (3)	0.8688 (2)	0.0301 (6)
O51B	0.4109 (3)	0.3742 (2)	0.96312 (16)	0.0456 (6)
O52B	0.5704 (2)	0.4114 (2)	0.80818 (16)	0.0376 (5)
C6B	0.44795 (15)	0.28551 (13)	0.70956 (10)	0.0296 (6)
H6B	0.4816	0.3551	0.6632	0.046 (9)*
O1W	0.28635 (15)	0.62163 (13)	0.53915 (10)	0.0643 (7)
H11	0.3675	0.6448	0.5266	0.080*
H12	0.3263	0.5333	0.5247	0.080*
O2W	0.01827 (15)	0.91810 (13)	0.16977 (10)	0.0664 (7)
H21	0.0887	0.9370	0.1178	0.083*
H22	−0.0638	0.9943	0.1650	0.083*
O3W	0.13861 (15)	0.14870 (13)	0.17162 (10)	0.1002 (12)
H31	0.1470	0.0911	0.2331	0.125*
H32	0.1826	0.0847	0.1323	0.125*
O4W	0.19582 (15)	−0.00158 (13)	0.56437 (10)	0.1127 (13)
H41	0.1759	0.0081	0.5012	0.141*
H42	0.2513	0.0518	0.5409	0.141*
O5W	0.80533 (15)	0.26304 (13)	0.26316 (10)	0.1050 (16)	0.80
H51	0.9038	0.2293	0.2361	0.131*	0.80
H52	0.7970	0.3086	0.3088	0.131*	0.80
O6W	0.86206 (15)	0.02992 (13)	0.61994 (10)	0.0872 (14)	0.70
H61	0.9580	0.0208	0.6040	0.109*	0.70

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0261 (11)	0.0320 (11)	0.0297 (11)	−0.0124 (9)	−0.0020 (9)	−0.0040 (9)
C2A	0.0354 (15)	0.0347 (14)	0.0345 (14)	−0.0171 (12)	−0.0047 (11)	−0.0008 (11)
C3A	0.0398 (16)	0.0329 (14)	0.0396 (15)	−0.0149 (12)	−0.0056 (12)	−0.0076 (12)
N4A	0.0342 (13)	0.0393 (14)	0.0318 (13)	−0.0111 (11)	−0.0043 (10)	−0.0056 (10)
C5A	0.0360 (16)	0.0439 (16)	0.0351 (14)	−0.0218 (13)	−0.0071 (12)	−0.0034 (12)
C6A	0.0400 (16)	0.0428 (16)	0.0337 (15)	−0.0144 (13)	−0.0114 (12)	−0.0002 (12)
N7A	0.0437 (14)	0.0315 (12)	0.0278 (11)	−0.0195 (10)	−0.0055 (10)	−0.0023 (9)
C8A	0.0279 (14)	0.0370 (15)	0.0399 (15)	−0.0116 (12)	0.0014 (12)	−0.0054 (12)
C9A	0.0465 (18)	0.0463 (17)	0.0323 (14)	−0.0198 (14)	0.0033 (13)	−0.0100 (12)
N10A	0.0435 (15)	0.0493 (15)	0.0384 (13)	−0.0195 (13)	−0.0017 (12)	−0.0137 (12)
C1B	0.0273 (13)	0.0291 (13)	0.0268 (13)	−0.0105 (11)	−0.0047 (10)	−0.0022 (10)
C11B	0.0398 (16)	0.0372 (15)	0.0308 (14)	−0.0166 (13)	−0.0080 (12)	−0.0025 (12)
O11B	0.0826 (18)	0.0752 (16)	0.0314 (11)	−0.0556 (15)	−0.0162 (11)	0.0099 (11)
O12B	0.109 (2)	0.0617 (15)	0.0367 (12)	−0.0521 (15)	−0.0273 (13)	0.0002 (10)
C2B	0.0288 (13)	0.0254 (12)	0.0316 (13)	−0.0116 (10)	−0.0046 (10)	−0.0053 (10)
C3B	0.0258 (13)	0.0237 (12)	0.0299 (13)	−0.0098 (10)	−0.0026 (10)	−0.0049 (10)
C31B	0.0276 (13)	0.0274 (13)	0.0321 (14)	−0.0117 (11)	−0.0039 (10)	−0.0029 (10)
O31B	0.0432 (11)	0.0299 (10)	0.0373 (10)	−0.0213 (9)	−0.0040 (8)	−0.0055 (8)
O32B	0.0618 (14)	0.0510 (12)	0.0293 (10)	−0.0372 (11)	0.0034 (9)	−0.0062 (9)
C4B	0.0293 (13)	0.0303 (13)	0.0265 (13)	−0.0130 (11)	−0.0028 (10)	−0.0050 (10)
C5B	0.0248 (13)	0.0267 (12)	0.0304 (13)	−0.0117 (10)	−0.0024 (10)	−0.0061 (10)
C51B	0.0320 (14)	0.0296 (13)	0.0294 (13)	−0.0151 (11)	−0.0004 (11)	−0.0072 (10)
O51B	0.0587 (14)	0.0501 (12)	0.0373 (11)	−0.0335 (11)	0.0102 (10)	−0.0202 (9)
O52B	0.0413 (12)	0.0429 (11)	0.0381 (10)	−0.0288 (10)	0.0018 (8)	−0.0099 (8)
C6B	0.0308 (14)	0.0283 (13)	0.0301 (13)	−0.0152 (11)	−0.0024 (10)	−0.0036 (10)
O1W	0.0659 (17)	0.0718 (17)	0.0622 (16)	−0.0350 (14)	−0.0161 (13)	−0.0064 (13)
O2W	0.0500 (15)	0.0679 (16)	0.0657 (16)	−0.0254 (13)	−0.0085 (12)	0.0097 (13)
O3W	0.130 (3)	0.101 (3)	0.096 (2)	−0.068 (2)	0.003 (2)	−0.043 (2)
O4W	0.129 (3)	0.143 (3)	0.113 (3)	−0.092 (3)	−0.026 (2)	−0.024 (3)
O5W	0.072 (3)	0.166 (5)	0.111 (3)	−0.051 (3)	0.006 (2)	−0.091 (3)
O6W	0.122 (4)	0.080 (3)	0.079 (3)	−0.042 (3)	−0.038 (3)	−0.020 (2)

Geometric parameters (Å, º)

N1A—C2A	1.471 (4)	C1B—C6B	1.386 (3)
N1A—C8A	1.465 (4)	C1B—C2B	1.394 (4)
N1A—C5A	1.472 (4)	C1B—C11B	1.509 (4)
C2A—C3A	1.506 (4)	C11B—O12B	1.237 (4)
C2A—H21A	0.97	C11B—O11B	1.262 (3)
C2A—H22A	0.97	C2B—C3B	1.386 (4)
C3A—N4A	1.483 (4)	C2B—H2B	0.93
C3A—H31A	0.97	C3B—C4B	1.386 (4)
C3A—H32A	0.97	C3B—C31B	1.513 (3)
N4A—H41A	0.89	C31B—O32B	1.245 (3)
N4A—H42A	0.89	C31B—O31B	1.269 (3)
N4A—H43A	0.89	C4B—C5B	1.390 (4)
C5A—C6A	1.511 (4)	C4B—H4B	0.93
C5A—H51A	0.97	C5B—C6B	1.385 (3)
C5A—H52A	0.97	C5B—C51B	1.508 (3)
C6A—N7A	1.478 (4)	C51B—O51B	1.234 (3)
C6A—H61A	0.97	C51B—O52B	1.269 (3)
C6A—H62A	0.97	C6B—H6B	0.9300
N7A—H71A	0.89	O1W—H11	0.8796
N7A—H72A	0.89	O1W—H12	0.9009
N7A—H73A	0.89	O2W—H21	0.8596
C8A—C9A	1.509 (4)	O2W—H22	0.8379
C8A—H81A	0.97	O3W—H31	0.8504
C8A—H82A	0.97	O3W—H32	0.8559
C9A—N10A	1.478 (4)	O4W—H41	0.8595
C9A—H91A	0.97	O4W—H42	0.8862
C9A—H92A	0.97	O5W—H51	0.8500
N10A—H11A	0.89	O5W—H52	0.8397
N10A—H12A	0.89	O6W—H61	0.8496
N10A—H13A	0.89
C2A—N1A—C8A	110.0 (2)	N10A—C9A—C8A	112.1 (2)
C2A—N1A—C5A	111.0 (2)	N10A—C9A—H91A	109.2
C8A—N1A—C5A	110.7 (2)	C8A—C9A—H91A	109.2
N1A—C2A—C3A	112.6 (2)	N10A—C9A—H92A	109.2
N1A—C2A—H21A	109.1	C8A—C9A—H92A	109.2
C3A—C2A—H21A	109.1	H91A—C9A—H92A	107.9
N1A—C2A—H22A	109.1	C9A—N10A—H11A	109.5
C3A—C2A—H22A	109.1	C9A—N10A—H12A	109.5
H21A—C2A—H22A	107.8	H11A—N10A—H12A	109.5
N4A—C3A—C2A	111.0 (2)	C9A—N10A—H13A	109.5
N4A—C3A—H31A	109.4	H11A—N10A—H13A	109.5
C2A—C3A—H31A	109.4	H12A—N10A—H13A	109.5
N4A—C3A—H32A	109.4	C6B—C1B—C2B	118.4 (2)
C2A—C3A—H32A	109.4	C6B—C1B—C11B	121.5 (2)
H31A—C3A—H32A	108.0	C2B—C1B—C11B	120.0 (2)
C3A—N4A—H41A	109.5	O12B—C11B—O11B	123.1 (3)
C3A—N4A—H42A	109.5	O12B—C11B—C1B	119.0 (2)
H41A—N4A—H42A	109.5	O11B—C11B—C1B	117.9 (2)
C3A—N4A—H43A	109.5	C3B—C2B—C1B	121.0 (2)
H41A—N4A—H43A	109.5	C3B—C2B—H2B	119.5
H42A—N4A—H43A	109.5	C1B—C2B—H2B	119.5
N1A—C5A—C6A	111.7 (2)	C4B—C3B—C2B	119.6 (2)
N1A—C5A—H51A	109.3	C4B—C3B—C31B	120.5 (2)
C6A—C5A—H51A	109.3	C2B—C3B—C31B	119.9 (2)
N1A—C5A—H52A	109.3	O32B—C31B—O31B	124.3 (2)
C6A—C5A—H52A	109.3	O32B—C31B—C3B	118.2 (2)
H51A—C5A—H52A	107.9	O31B—C31B—C3B	117.5 (2)
N7A—C6A—C5A	110.4 (2)	C3B—C4B—C5B	120.2 (2)
N7A—C6A—H61A	109.6	C3B—C4B—H4B	119.9
C5A—C6A—H61A	109.6	C5B—C4B—H4B	119.9
N7A—C6A—H62A	109.6	C6B—C5B—C4B	119.3 (2)
C5A—C6A—H62A	109.6	C6B—C5B—C51B	120.6 (2)
H61A—C6A—H62A	108.1	C4B—C5B—C51B	120.0 (2)
C6A—N7A—H71A	109.5	O51B—C51B—O52B	124.1 (2)
C6A—N7A—H72A	109.5	O51B—C51B—C5B	118.4 (2)
H71A—N7A—H72A	109.5	O52B—C51B—C5B	117.4 (2)
C6A—N7A—H73A	109.5	C1B—C6B—C5B	121.34 (17)
H71A—N7A—H73A	109.5	C1B—C6B—H6B	119.3
H72A—N7A—H73A	109.5	C5B—C6B—H6B	119.3
N1A—C8A—C9A	113.1 (2)	H11—O1W—H12	106.5
N1A—C8A—H81A	109.0	H21—O2W—H22	104.0
C9A—C8A—H81A	109.0	H31—O3W—H32	96.3
N1A—C8A—H82A	109.0	H41—O4W—H42	95.4
C9A—C8A—H82A	109.0	H51—O5W—H52	105.1
H81A—C8A—H82A	107.8
C8A—N1A—C2A—C3A	−158.1 (2)	C4B—C3B—C31B—O32B	9.3 (4)
C5A—N1A—C2A—C3A	79.1 (3)	C2B—C3B—C31B—O32B	−167.2 (2)
N1A—C2A—C3A—N4A	67.8 (3)	C4B—C3B—C31B—O31B	−172.3 (2)
C2A—N1A—C5A—C6A	−156.3 (2)	C2B—C3B—C31B—O31B	11.2 (4)
C8A—N1A—C5A—C6A	81.2 (3)	C2B—C3B—C4B—C5B	−2.6 (4)
N1A—C5A—C6A—N7A	58.7 (3)	C31B—C3B—C4B—C5B	−179.2 (2)
C2A—N1A—C8A—C9A	77.0 (3)	C3B—C4B—C5B—C6B	2.6 (4)
C5A—N1A—C8A—C9A	−159.9 (2)	C3B—C4B—C5B—C51B	179.8 (2)
N1A—C8A—C9A—N10A	67.3 (3)	C6B—C5B—C51B—O51B	152.7 (2)
C6B—C1B—C11B—O12B	−175.0 (3)	C4B—C5B—C51B—O51B	−24.4 (4)
C2B—C1B—C11B—O12B	1.2 (4)	C6B—C5B—C51B—O52B	−27.1 (3)
C6B—C1B—C11B—O11B	2.0 (4)	C4B—C5B—C51B—O52B	155.7 (3)
C2B—C1B—C11B—O11B	178.2 (3)	C2B—C1B—C6B—C5B	−2.1 (3)
C6B—C1B—C2B—C3B	2.1 (4)	C11B—C1B—C6B—C5B	174.2 (2)
C11B—C1B—C2B—C3B	−174.3 (2)	C4B—C5B—C6B—C1B	−0.2 (3)
C1B—C2B—C3B—C4B	0.3 (4)	C51B—C5B—C6B—C1B	−177.3 (2)
C1B—C2B—C3B—C31B	176.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H41A···O11B	0.89	2.11	2.944 (3)	156
N4A—H41A···O12B	0.89	2.43	3.168 (3)	141
N4A—H42A···O52B^i	0.89	1.97	2.847 (3)	166
N4A—H43A···O31B^ii	0.89	2.05	2.885 (4)	155
N4A—H43A···O5W	0.89	2.59	3.113 (3)	118
N7A—H71A···O52B^i	0.89	2.06	2.921 (3)	162
N7A—H72A···O31B^iii	0.89	1.91	2.796 (3)	176
N7A—H73A···O51B^iv	0.89	1.90	2.760 (4)	162
N10A—H11A···O52B^i	0.89	1.89	2.771 (3)	169
N10A—H12A···O1W	0.89	2.17	2.917 (3)	141
N10A—H12A···O6W^i	0.89	2.39	2.916 (3)	118
N10A—H13A···O2W	0.89	1.92	2.758 (3)	157
O1W—H11···O11B^i	0.88 (3)	1.89 (3)	2.755 (3)	170 (3)
O1W—H12···O11B	0.90 (4)	2.02 (4)	2.921 (4)	173 (3)
O2W—H21···O32B^iii	0.86 (3)	1.84 (3)	2.694 (2)	171 (3)
O2W—H22···O31B^v	0.84 (4)	2.06 (4)	2.828 (4)	153 (3)
O3W—H31···O6W^ii	0.85 (3)	1.97 (3)	2.814 (2)	173 (3)
O3W—H32···O32B^iv	0.86 (3)	1.97 (3)	2.814 (3)	170 (3)
O4W—H41···O6W^ii	0.86 (3)	1.90 (3)	2.730 (2)	162 (3)
O4W—H42···O12B	0.89 (3)	1.85 (3)	2.730 (3)	172 (3)
O5W—H51···O3W^vi	0.85 (3)	2.03 (3)	2.878 (3)	180 (3)
O5W—H52···O1W^i	0.84 (3)	2.13 (3)	2.916 (2)	156 (3)
O6W—H61···O4W^vi	0.85 (3)	2.11 (3)	2.955 (3)	180 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, y+1, z−1; (iv) x, y, z−1; (v) −x, −y+1, −z+1; (vi) x+1, y, z.