Hydrogen-bonding patterns in bis­(trimethoprim) dipicolinate penta­hydrate

Hemamalini, M.; Muthiah, P.T.; Bocelli, G.; Cantoni, A.

doi:10.1107/S1600536805020167

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Hydrogen-bonding patterns in bis(trimethoprim) dipicolinate pentahydrate

M. Hemamalini, P. T. Muthiah, G. Bocelli and A. Cantoni

In the title compound, 2C₁₄H₁₉N₄O₃⁺·C₇H₃NO₄²⁻·5H₂O, the asymmetric unit contains two trimethoprim cations (A and B), a dipicolinate anion and five water molecules. One of the picolinate carboxylate groups interacts with cation A via a pair of N—H

O hydrogen bonds, forming a ring motif $R{_2^2}$ (8). A loop of O—H

O hydrogen bonds is formed between four water molecules and the two carboxylate groups to form a supramolecular chain along the a axis. Molecules A and B constitute a base pair via N—H

N hydrogen bonds, and these base pairs are cross-linked by N—H

O and C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020167/lh6416sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020167/lh6416Isup2.hkl Contains datablock I

CCDC reference: 227940

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.057
wR factor = 0.160
Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H12    ..  H22     ..       1.91 Ang.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.41 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        O2A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.99
PLAT420_ALERT_2_C D-H Without Acceptor       N4B    -   H42B   ...          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: FEBO (Belletti, 1996); cell refinement: MolEN (Fair, 1990); data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

(2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidinium dipicolinate pentahydrate top

Crystal data top

2C₁₄H₁₉N₄O₃⁺·C₇H₃NO₄²⁻·5H₂O	F(000) = 1776
M_r = 837.85	D_x = 1.338 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 9.713 (2) Å	θ = 3.1–27.0°
b = 12.025 (3) Å	µ = 0.11 mm⁻¹
c = 35.703 (3) Å	T = 293 K
β = 94.23 (3)°	Block, colourless
V = 4158.7 (14) Å³	0.38 × 0.26 × 0.19 mm
Z = 4

Data collection top

Philips PW1100 diffractometer	4170 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 27.0°, θ_min = 3.1°
ω scans	h = −12→12
Absorption correction: part of the refinement model (ΔF) (SHELXA; Sheldrick, 1997)	k = 0→15
T_min = 0.961, T_max = 0.980	l = 0→45
9210 measured reflections	1 standard reflections every 100 reflections
9074 independent reflections	intensity decay: none

Refinement top

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)] = 0.057	H-atom parameters constrained
wR(F²) = 0.160	w = 1/[σ²(F_o²) + (0.0728P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
9074 reflections	Δρ_max = 0.33 e Å⁻³
532 parameters	Δρ_min = −0.35 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001Fc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (5)

Special details top

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

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1A	0.5277 (2)	0.00551 (17)	0.19165 (6)	0.0672 (9)
O2A	0.4094 (2)	0.12086 (17)	0.24403 (5)	0.0605 (8)
O3A	0.2905 (2)	0.31753 (18)	0.22869 (6)	0.0695 (9)
N1A	0.0646 (2)	0.10468 (17)	0.05921 (6)	0.0393 (7)
N2A	−0.0927 (2)	0.11773 (18)	0.00838 (6)	0.0511 (8)
N3A	0.0723 (2)	0.25576 (16)	0.01799 (5)	0.0344 (7)
N4A	0.2354 (2)	0.39029 (17)	0.02812 (6)	0.0442 (8)
C2A	0.0162 (3)	0.1608 (2)	0.02837 (7)	0.0347 (8)
C4A	0.1826 (3)	0.2955 (2)	0.03903 (7)	0.0334 (8)
C5A	0.2395 (2)	0.2391 (2)	0.07233 (7)	0.0336 (8)
C6A	0.1759 (3)	0.1447 (2)	0.08074 (7)	0.0386 (9)
C7A	0.3676 (3)	0.2815 (2)	0.09441 (7)	0.0462 (10)
C8A	0.3859 (3)	0.2398 (2)	0.13451 (7)	0.0400 (9)
C9A	0.3312 (3)	0.3010 (2)	0.16246 (8)	0.0472 (10)
C10A	0.3418 (3)	0.2633 (2)	0.19941 (8)	0.0454 (10)
C11A	0.4084 (3)	0.1633 (2)	0.20816 (7)	0.0442 (10)
C12A	0.4649 (3)	0.1031 (2)	0.18027 (8)	0.0453 (10)
C13A	0.4537 (3)	0.1407 (2)	0.14327 (8)	0.0447 (10)
C14A	0.5937 (4)	−0.0574 (3)	0.16484 (11)	0.0867 (16)
C15A	0.5147 (4)	0.1564 (4)	0.26973 (10)	0.114 (2)
C16A	0.2072 (5)	0.4124 (3)	0.22065 (11)	0.0974 (19)
O1B	0.7765 (2)	0.32451 (18)	0.24788 (6)	0.0674 (9)
O2B	0.9412 (2)	0.15273 (17)	0.26471 (5)	0.0626 (8)
O3B	1.0566 (2)	0.03647 (18)	0.21136 (5)	0.0655 (8)
N1B	1.0298 (2)	0.49072 (18)	0.09778 (6)	0.0449 (8)
N2B	1.0387 (2)	0.62059 (19)	0.05104 (6)	0.0560 (9)
N3B	0.8715 (2)	0.48534 (17)	0.04479 (6)	0.0385 (7)
N4B	0.7097 (2)	0.3467 (2)	0.03922 (6)	0.0540 (9)
C2B	0.9785 (3)	0.5318 (2)	0.06421 (7)	0.0396 (9)
C4B	0.8136 (3)	0.3949 (2)	0.05933 (7)	0.0373 (9)
C5B	0.8611 (3)	0.3493 (2)	0.09539 (7)	0.0384 (8)
C6B	0.9700 (3)	0.4009 (2)	0.11283 (7)	0.0433 (9)
C7B	0.7899 (3)	0.2514 (2)	0.11187 (7)	0.0516 (10)
C8B	0.8360 (3)	0.2267 (2)	0.15255 (7)	0.0448 (10)
C9B	0.9283 (3)	0.1426 (2)	0.16177 (7)	0.0470 (10)
C10B	0.9676 (3)	0.1193 (2)	0.19951 (8)	0.0473 (10)
C11B	0.9136 (3)	0.1812 (2)	0.22763 (7)	0.0458 (10)
C12B	0.8221 (3)	0.2677 (2)	0.21819 (8)	0.0480 (10)
C13B	0.7837 (3)	0.2893 (2)	0.18068 (8)	0.0500 (10)
C14B	0.6886 (4)	0.4174 (3)	0.24005 (11)	0.0920 (17)
C15B	1.0629 (4)	0.2001 (4)	0.28273 (9)	0.0872 (18)
C16B	1.1173 (4)	−0.0281 (3)	0.18386 (9)	0.0710 (12)
O4	0.4128 (2)	0.53599 (18)	0.07495 (6)	0.0751 (9)
O5	0.4573 (3)	0.6459 (2)	0.02803 (6)	0.0944 (10)
O6	0.7868 (2)	0.93134 (16)	0.04534 (6)	0.0609 (8)
O7	0.9608 (2)	0.91555 (16)	0.08868 (6)	0.0614 (8)
N5	0.6698 (2)	0.74232 (17)	0.07016 (6)	0.0406 (8)
C17	0.6045 (3)	0.6553 (2)	0.08396 (7)	0.0405 (9)
C18	0.6446 (3)	0.6100 (2)	0.11861 (8)	0.0543 (11)
C19	0.7564 (3)	0.6547 (3)	0.13928 (9)	0.0710 (12)
C20	0.8249 (3)	0.7431 (2)	0.12482 (8)	0.0581 (11)
C21	0.7787 (3)	0.7855 (2)	0.09025 (7)	0.0387 (9)
C22	0.8465 (3)	0.8847 (2)	0.07334 (8)	0.0448 (10)
C23	0.4821 (3)	0.6087 (2)	0.05994 (8)	0.0526 (11)
O1W	0.2018 (3)	0.8005 (2)	0.10661 (10)	0.1239 (14)
O2W	0.3449 (3)	0.8911 (3)	0.05177 (9)	0.1569 (19)
O3W	0.5736 (3)	0.8311 (2)	−0.00256 (6)	0.0884 (10)
O4W	0.2566 (2)	0.59006 (18)	0.13290 (6)	0.0746 (9)
O5W	0.5593 (4)	0.0682 (3)	0.05840 (7)	0.191 (2)
H1A	0.02070	0.03440	0.06660	0.0470*
H2A	−0.12700	0.15130	−0.01140	0.0610*
H2B	−0.12850	0.05640	0.01530	0.0610*
H4A	0.19920	0.42370	0.00850	0.0530*
H4B	0.30580	0.41870	0.04070	0.0530*
H6A	0.20860	0.10490	0.10190	0.0460*
H7A	0.44780	0.26010	0.08140	0.0550*
H7B	0.36430	0.36210	0.09480	0.0550*
H9A	0.28740	0.36820	0.15660	0.0570*
H13A	0.49170	0.09950	0.12450	0.0540*
H14A	0.52630	−0.08330	0.14580	0.1040*
H14B	0.63960	−0.11990	0.17690	0.1040*
H14C	0.66010	−0.01150	0.15360	0.1040*
H15A	0.60170	0.12970	0.26230	0.1360*
H15B	0.49920	0.12790	0.29420	0.1360*
H15C	0.51590	0.23620	0.27050	0.1360*
H16A	0.17210	0.43940	0.24340	0.1170*
H16B	0.26170	0.46940	0.21000	0.1170*
H16C	0.13160	0.39300	0.20310	0.1170*
H1B	1.10400	0.52370	0.11070	0.0540*
H6B	1.00580	0.37440	0.13600	0.0520*
H9B	0.96450	0.10100	0.14280	0.0560*
H13B	0.72230	0.34680	0.17440	0.0600*
H21A	1.00870	0.64850	0.02980	0.0670*
H22B	1.10790	0.65040	0.06370	0.0670*
H41A	0.68140	0.37350	0.01770	0.0650*
H42B	0.67060	0.28880	0.04770	0.0650*
H71A	0.69120	0.26490	0.11000	0.0620*
H72B	0.80660	0.18600	0.09690	0.0620*
H141	0.60550	0.39320	0.22620	0.1100*
H142	0.66590	0.45100	0.26320	0.1100*
H143	0.73510	0.47070	0.22540	0.1100*
H151	1.05610	0.27980	0.28200	0.1050*
H152	1.07340	0.17580	0.30840	0.1050*
H153	1.14140	0.17680	0.26990	0.1050*
H161	1.17210	0.01900	0.16910	0.0850*
H162	1.17500	−0.08430	0.19600	0.0850*
H163	1.04620	−0.06280	0.16780	0.0850*
H18	0.59680	0.55010	0.12780	0.0650*
H19	0.78510	0.62560	0.16270	0.0850*
H20	0.90140	0.77390	0.13820	0.0700*
H11	0.11420	0.84000	0.10630	0.1490*
H12	0.24650	0.82310	0.08420	0.1490*
H21	0.40990	0.88940	0.03200	0.1880*
H22	0.39920	0.91040	0.07090	0.1880*
H31	0.64340	0.86630	0.01330	0.1060*
H32	0.55360	0.76330	0.00900	0.1060*
H41	0.23760	0.66630	0.12810	0.0900*
H42	0.32480	0.56790	0.11590	0.0900*
H51	0.64910	0.05180	0.05270	0.2290*
H52	0.53160	0.11870	0.03850	0.2290*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0868 (17)	0.0504 (13)	0.0635 (14)	0.0228 (12)	0.0002 (12)	0.0160 (11)
O2A	0.0708 (14)	0.0649 (14)	0.0439 (12)	−0.0100 (12)	−0.0090 (10)	0.0170 (10)
O3A	0.0898 (17)	0.0680 (15)	0.0491 (13)	0.0187 (13)	−0.0057 (12)	−0.0093 (11)
N1A	0.0417 (13)	0.0311 (11)	0.0440 (13)	−0.0125 (10)	−0.0045 (10)	0.0082 (10)
N2A	0.0534 (15)	0.0409 (13)	0.0559 (15)	−0.0194 (12)	−0.0173 (12)	0.0110 (11)
N3A	0.0366 (12)	0.0318 (12)	0.0339 (12)	−0.0088 (10)	−0.0038 (9)	0.0043 (9)
N4A	0.0468 (14)	0.0385 (13)	0.0448 (13)	−0.0148 (11)	−0.0131 (11)	0.0147 (11)
C2A	0.0335 (15)	0.0324 (14)	0.0371 (15)	−0.0044 (12)	−0.0040 (12)	−0.0007 (12)
C4A	0.0342 (15)	0.0296 (14)	0.0361 (14)	−0.0043 (11)	0.0014 (11)	0.0023 (11)
C5A	0.0333 (14)	0.0318 (14)	0.0350 (14)	−0.0051 (11)	−0.0019 (11)	0.0038 (11)
C6A	0.0393 (15)	0.0380 (15)	0.0374 (15)	−0.0048 (12)	−0.0048 (12)	0.0074 (12)
C7A	0.0446 (17)	0.0481 (17)	0.0439 (16)	−0.0168 (14)	−0.0105 (13)	0.0100 (13)
C8A	0.0392 (15)	0.0390 (15)	0.0398 (15)	−0.0123 (13)	−0.0112 (12)	0.0078 (13)
C9A	0.0493 (18)	0.0375 (16)	0.0519 (18)	−0.0009 (13)	−0.0162 (14)	0.0040 (14)
C10A	0.0515 (18)	0.0408 (16)	0.0422 (16)	−0.0023 (14)	−0.0087 (14)	−0.0046 (13)
C11A	0.0512 (18)	0.0424 (16)	0.0372 (16)	−0.0099 (14)	−0.0089 (13)	0.0065 (13)
C12A	0.0470 (17)	0.0351 (15)	0.0518 (18)	−0.0037 (13)	−0.0093 (14)	0.0102 (14)
C13A	0.0427 (16)	0.0459 (17)	0.0447 (17)	−0.0030 (13)	−0.0014 (13)	0.0010 (13)
C14A	0.104 (3)	0.061 (2)	0.095 (3)	0.031 (2)	0.007 (2)	0.005 (2)
C15A	0.108 (3)	0.169 (5)	0.057 (2)	−0.037 (3)	−0.038 (2)	0.040 (3)
C16A	0.128 (4)	0.078 (3)	0.085 (3)	0.043 (3)	−0.001 (2)	−0.013 (2)
O1B	0.0795 (17)	0.0653 (15)	0.0582 (13)	0.0089 (13)	0.0113 (12)	−0.0081 (12)
O2B	0.0795 (16)	0.0689 (14)	0.0385 (12)	−0.0060 (12)	−0.0023 (11)	0.0100 (10)
O3B	0.0817 (16)	0.0663 (14)	0.0482 (13)	0.0212 (13)	0.0031 (11)	0.0086 (11)
N1B	0.0408 (13)	0.0534 (14)	0.0382 (13)	−0.0131 (11)	−0.0127 (10)	0.0094 (11)
N2B	0.0597 (17)	0.0536 (16)	0.0512 (15)	−0.0206 (13)	−0.0188 (12)	0.0173 (12)
N3B	0.0387 (13)	0.0381 (12)	0.0374 (12)	−0.0026 (10)	−0.0069 (10)	0.0052 (10)
N4B	0.0541 (15)	0.0638 (16)	0.0413 (14)	−0.0189 (13)	−0.0156 (12)	0.0109 (12)
C2B	0.0430 (16)	0.0360 (15)	0.0387 (15)	−0.0005 (13)	−0.0049 (13)	0.0061 (12)
C4B	0.0334 (15)	0.0411 (15)	0.0367 (15)	−0.0015 (12)	−0.0029 (12)	0.0004 (12)
C5B	0.0377 (15)	0.0422 (15)	0.0345 (14)	−0.0032 (13)	−0.0035 (12)	0.0066 (12)
C6B	0.0385 (16)	0.0514 (17)	0.0385 (15)	−0.0063 (14)	−0.0075 (13)	0.0153 (13)
C7B	0.0490 (18)	0.0616 (19)	0.0423 (16)	−0.0147 (15)	−0.0088 (13)	0.0138 (14)
C8B	0.0439 (17)	0.0499 (17)	0.0398 (16)	−0.0138 (14)	−0.0021 (13)	0.0102 (14)
C9B	0.0516 (18)	0.0540 (18)	0.0358 (16)	−0.0078 (15)	0.0062 (13)	0.0035 (13)
C10B	0.0525 (18)	0.0447 (17)	0.0446 (17)	−0.0018 (15)	0.0022 (14)	0.0097 (14)
C11B	0.0512 (18)	0.0499 (18)	0.0359 (16)	−0.0093 (15)	0.0013 (13)	0.0047 (14)
C12B	0.0495 (18)	0.0489 (18)	0.0460 (17)	−0.0095 (15)	0.0059 (14)	0.0020 (15)
C13B	0.0463 (18)	0.0449 (17)	0.0580 (19)	−0.0041 (14)	−0.0018 (15)	0.0108 (15)
C14B	0.110 (3)	0.069 (3)	0.098 (3)	0.023 (2)	0.015 (2)	−0.015 (2)
C15B	0.076 (3)	0.131 (4)	0.052 (2)	0.000 (2)	−0.0129 (19)	0.000 (2)
C16B	0.075 (2)	0.070 (2)	0.067 (2)	0.0151 (19)	−0.0024 (18)	−0.0040 (19)
O4	0.0862 (16)	0.0642 (15)	0.0711 (15)	−0.0495 (13)	−0.0196 (12)	0.0097 (12)
O5	0.0996 (19)	0.115 (2)	0.0612 (15)	−0.0632 (16)	−0.0438 (14)	0.0330 (14)
O6	0.0489 (12)	0.0547 (13)	0.0771 (15)	−0.0112 (10)	−0.0081 (11)	0.0288 (11)
O7	0.0463 (13)	0.0520 (13)	0.0828 (15)	−0.0236 (10)	−0.0154 (11)	0.0167 (11)
N5	0.0409 (13)	0.0374 (13)	0.0421 (13)	−0.0105 (11)	−0.0063 (10)	0.0072 (10)
C17	0.0417 (16)	0.0346 (15)	0.0436 (16)	−0.0086 (13)	−0.0072 (13)	0.0070 (12)
C18	0.0538 (19)	0.0512 (18)	0.0553 (18)	−0.0209 (15)	−0.0137 (15)	0.0212 (15)
C19	0.070 (2)	0.081 (2)	0.057 (2)	−0.031 (2)	−0.0293 (17)	0.0345 (18)
C20	0.0515 (19)	0.059 (2)	0.060 (2)	−0.0250 (16)	−0.0210 (15)	0.0136 (16)
C21	0.0364 (15)	0.0335 (14)	0.0450 (16)	−0.0069 (12)	−0.0060 (12)	0.0046 (12)
C22	0.0381 (16)	0.0338 (15)	0.0619 (19)	−0.0033 (13)	0.0005 (14)	0.0070 (14)
C23	0.056 (2)	0.0489 (18)	0.0502 (18)	−0.0206 (16)	−0.0146 (15)	0.0061 (15)
O1W	0.0790 (19)	0.092 (2)	0.202 (3)	0.0165 (16)	0.019 (2)	0.044 (2)
O2W	0.096 (2)	0.275 (5)	0.103 (2)	0.060 (3)	0.0299 (18)	0.016 (3)
O3W	0.117 (2)	0.0767 (16)	0.0662 (15)	−0.0053 (15)	−0.0280 (14)	0.0202 (13)
O4W	0.0626 (14)	0.0759 (16)	0.0816 (16)	−0.0211 (12)	−0.0200 (12)	0.0070 (13)
O5W	0.216 (4)	0.288 (5)	0.0641 (18)	0.185 (4)	−0.022 (2)	−0.027 (2)

Geometric parameters (Å, º) top

O1A—C12A	1.370 (3)	C8A—C9A	1.378 (4)
O1A—C14A	1.411 (4)	C8A—C13A	1.386 (4)
O2A—C11A	1.378 (3)	C9A—C10A	1.392 (4)
O2A—C15A	1.390 (4)	C10A—C11A	1.390 (4)
O3A—C10A	1.358 (3)	C11A—C12A	1.377 (4)
O3A—C16A	1.416 (5)	C12A—C13A	1.393 (4)
N1A—C2A	1.346 (3)	C6A—H6A	0.9302
N1A—C6A	1.367 (3)	C7A—H7B	0.9699
N2A—C2A	1.336 (3)	C7A—H7A	0.9707
N3A—C4A	1.350 (3)	C9A—H9A	0.9299
N3A—C2A	1.330 (3)	C13A—H13A	0.9313
N4A—C4A	1.320 (3)	C14A—H14B	0.9595
O1B—C12B	1.362 (3)	C14A—H14A	0.9602
O1B—C14B	1.421 (4)	C14A—H14C	0.9591
O2B—C15B	1.422 (4)	C15A—H15A	0.9595
O2B—C11B	1.375 (3)	C15A—H15C	0.9600
O3B—C10B	1.365 (3)	C15A—H15B	0.9606
O3B—C16B	1.414 (4)	C16A—H16B	0.9614
N1B—C2B	1.357 (3)	C16A—H16C	0.9583
N1B—C6B	1.356 (3)	C16A—H16A	0.9603
N2B—C2B	1.320 (3)	C4B—C5B	1.443 (4)
N3B—C2B	1.329 (3)	C5B—C7B	1.507 (4)
N3B—C4B	1.346 (3)	C5B—C6B	1.340 (4)
N4B—C4B	1.328 (3)	C7B—C8B	1.517 (4)
O4—C23	1.248 (3)	C8B—C9B	1.375 (4)
O5—C23	1.231 (4)	C8B—C13B	1.382 (4)
O6—C22	1.251 (3)	C9B—C10B	1.401 (4)
O7—C22	1.257 (3)	C10B—C11B	1.384 (4)
N5—C21	1.338 (3)	C11B—C12B	1.393 (4)
N5—C17	1.336 (3)	C12B—C13B	1.388 (4)
O1W—H12	0.9766	C6B—H6B	0.9297
O1W—H11	0.9738	C7B—H72B	0.9712
O2W—H21	0.9813	C7B—H71A	0.9698
O2W—H22	0.8634	C9B—H9B	0.9315
N1A—H1A	0.9911	C13B—H13B	0.9297
N2A—H2A	0.8591	C14B—H141	0.9601
N2A—H2B	0.8594	C14B—H143	0.9608
O3W—H31	0.9502	C14B—H142	0.9602
O3W—H32	0.9405	C15B—H153	0.9598
N4A—H4A	0.8599	C15B—H152	0.9602
N4A—H4B	0.8606	C15B—H151	0.9609
N1B—H1B	0.9168	C16B—H161	0.9608
N2B—H21A	0.8602	C16B—H162	0.9606
N2B—H22B	0.8601	C16B—H163	0.9599
N4B—H41A	0.8594	C17—C18	1.381 (4)
N4B—H42B	0.8588	C17—C23	1.521 (4)
O4W—H42	0.9683	C18—C19	1.376 (4)
O4W—H41	0.9483	C19—C20	1.375 (4)
O5W—H52	0.9580	C20—C21	1.379 (4)
O5W—H51	0.9313	C21—C22	1.510 (4)
C4A—C5A	1.443 (4)	C18—H18	0.9298
C5A—C6A	1.337 (3)	C19—H19	0.9300
C5A—C7A	1.512 (4)	C20—H20	0.9301
C7A—C8A	1.515 (4)

C12A—O1A—C14A	118.2 (2)	N1A—C6A—H6A	118.95
C11A—O2A—C15A	117.0 (2)	C8A—C7A—H7A	108.79
C10A—O3A—C16A	117.9 (2)	H7A—C7A—H7B	107.48
C2A—N1A—C6A	119.8 (2)	C5A—C7A—H7A	108.65
C2A—N3A—C4A	118.3 (2)	C5A—C7A—H7B	108.53
N1A—C2A—N3A	122.2 (2)	C8A—C7A—H7B	108.60
N2A—C2A—N3A	120.6 (2)	C10A—C9A—H9A	119.81
N1A—C2A—N2A	117.2 (2)	C8A—C9A—H9A	119.72
N3A—C4A—C5A	122.2 (2)	C8A—C13A—H13A	120.13
N4A—C4A—C5A	121.0 (2)	C12A—C13A—H13A	120.16
N3A—C4A—N4A	116.8 (2)	H14A—C14A—H14B	109.49
N1A—C6A—C5A	122.1 (2)	O1A—C14A—H14C	109.18
O3A—C10A—C9A	124.6 (2)	H14A—C14A—H14C	109.56
O3A—C10A—C11A	115.7 (2)	O1A—C14A—H14A	109.52
O2A—C11A—C10A	120.0 (2)	O1A—C14A—H14B	109.57
O2A—C11A—C12A	120.1 (2)	H14B—C14A—H14C	109.51
O1A—C12A—C13A	124.1 (2)	H15B—C15A—H15C	109.45
O1A—C12A—C11A	115.3 (2)	H15A—C15A—H15B	109.41
C12B—O1B—C14B	117.8 (2)	H15A—C15A—H15C	109.47
C11B—O2B—C15B	115.6 (2)	O2A—C15A—H15C	109.45
C10B—O3B—C16B	118.2 (2)	O2A—C15A—H15B	109.49
C2B—N1B—C6B	120.0 (2)	O2A—C15A—H15A	109.56
C2B—N3B—C4B	118.1 (2)	H16B—C16A—H16C	109.43
N1B—C2B—N3B	122.0 (2)	O3A—C16A—H16A	109.52
N2B—C2B—N3B	120.3 (2)	H16A—C16A—H16C	109.43
N1B—C2B—N2B	117.7 (2)	O3A—C16A—H16C	109.59
N4B—C4B—C5B	119.8 (2)	H16A—C16A—H16B	109.49
N3B—C4B—C5B	122.4 (2)	O3A—C16A—H16B	109.36
N3B—C4B—N4B	117.8 (2)	C4B—C5B—C7B	121.3 (2)
N1B—C6B—C5B	122.1 (2)	C4B—C5B—C6B	115.3 (2)
O3B—C10B—C9B	124.4 (2)	C6B—C5B—C7B	123.4 (2)
O3B—C10B—C11B	115.6 (2)	C5B—C7B—C8B	114.5 (2)
O2B—C11B—C12B	119.6 (2)	C7B—C8B—C9B	120.9 (2)
O2B—C11B—C10B	120.5 (2)	C7B—C8B—C13B	119.4 (2)
O1B—C12B—C13B	125.3 (2)	C9B—C8B—C13B	119.7 (2)
O1B—C12B—C11B	115.1 (2)	C8B—C9B—C10B	120.2 (2)
C17—N5—C21	118.9 (2)	C9B—C10B—C11B	119.9 (2)
N5—C17—C18	121.9 (2)	C10B—C11B—C12B	119.7 (2)
N5—C17—C23	116.9 (2)	C11B—C12B—C13B	119.6 (2)
N5—C21—C20	121.9 (2)	C8B—C13B—C12B	120.8 (2)
N5—C21—C22	116.3 (2)	C5B—C6B—H6B	119.05
O7—C22—C21	117.1 (2)	N1B—C6B—H6B	118.85
O6—C22—C21	118.9 (2)	C5B—C7B—H72B	108.52
O6—C22—O7	123.9 (2)	C8B—C7B—H71A	108.61
O4—C23—C17	116.1 (2)	C5B—C7B—H71A	108.80
O4—C23—O5	125.2 (3)	C8B—C7B—H72B	108.59
O5—C23—C17	118.7 (3)	H71A—C7B—H72B	107.58
H11—O1W—H12	107.21	C10B—C9B—H9B	120.07
H21—O2W—H22	100.76	C8B—C9B—H9B	119.68
C6A—N1A—H1A	119.24	C8B—C13B—H13B	119.58
C2A—N1A—H1A	120.93	C12B—C13B—H13B	119.59
H2A—N2A—H2B	119.93	O1B—C14B—H141	109.46
C2A—N2A—H2A	120.05	O1B—C14B—H142	109.52
C2A—N2A—H2B	120.02	H141—C14B—H143	109.44
H31—O3W—H32	106.62	O1B—C14B—H143	109.37
C4A—N4A—H4B	119.98	H142—C14B—H143	109.57
C4A—N4A—H4A	119.95	H141—C14B—H142	109.46
H4A—N4A—H4B	120.07	O2B—C15B—H152	109.64
C6B—N1B—H1B	119.28	O2B—C15B—H153	109.28
C2B—N1B—H1B	120.72	O2B—C15B—H151	109.51
C2B—N2B—H21A	119.95	H152—C15B—H153	109.54
C2B—N2B—H22B	119.95	H151—C15B—H153	109.49
H21A—N2B—H22B	120.09	H151—C15B—H152	109.37
C4B—N4B—H41A	120.00	O3B—C16B—H163	109.57
H41A—N4B—H42B	119.91	H161—C16B—H162	109.50
C4B—N4B—H42B	120.10	H162—C16B—H163	109.50
H41—O4W—H42	106.61	O3B—C16B—H161	109.47
H51—O5W—H52	100.87	H161—C16B—H163	109.38
C6A—C5A—C7A	123.1 (2)	O3B—C16B—H162	109.40
C4A—C5A—C7A	121.4 (2)	C18—C17—C23	121.1 (2)
C4A—C5A—C6A	115.4 (2)	C17—C18—C19	119.0 (3)
C5A—C7A—C8A	114.6 (2)	C18—C19—C20	119.0 (3)
C7A—C8A—C9A	118.9 (2)	C19—C20—C21	119.2 (3)
C9A—C8A—C13A	119.9 (2)	C20—C21—C22	121.8 (2)
C7A—C8A—C13A	121.2 (2)	C17—C18—H18	120.43
C8A—C9A—C10A	120.5 (2)	C19—C18—H18	120.53
C9A—C10A—C11A	119.7 (2)	C20—C19—H19	120.48
C10A—C11A—C12A	119.7 (2)	C18—C19—H19	120.49
C11A—C12A—C13A	120.5 (2)	C21—C20—H20	120.48
C8A—C13A—C12A	119.7 (2)	C19—C20—H20	120.36
C5A—C6A—H6A	118.91

C14A—O1A—C12A—C11A	−176.9 (3)	O3A—C10A—C11A—O2A	5.2 (4)
C14A—O1A—C12A—C13A	4.6 (4)	C9A—C10A—C11A—O2A	−174.6 (3)
C15A—O2A—C11A—C10A	−87.2 (4)	C10A—C11A—C12A—C13A	−1.1 (4)
C15A—O2A—C11A—C12A	97.3 (3)	O2A—C11A—C12A—C13A	174.3 (3)
C16A—O3A—C10A—C9A	7.4 (4)	C10A—C11A—C12A—O1A	−179.7 (2)
C16A—O3A—C10A—C11A	−172.4 (3)	O2A—C11A—C12A—O1A	−4.2 (4)
C14B—O1B—C12B—C13B	−3.7 (4)	O1A—C12A—C13A—C8A	178.8 (3)
C14B—O1B—C12B—C11B	176.8 (3)	C11A—C12A—C13A—C8A	0.4 (4)
C15B—O2B—C11B—C12B	−96.6 (3)	N4B—C4B—C5B—C6B	177.3 (2)
C15B—O2B—C11B—C10B	88.3 (3)	N3B—C4B—C5B—C6B	−2.2 (4)
C16B—O3B—C10B—C9B	2.3 (4)	N3B—C4B—C5B—C7B	176.9 (2)
C16B—O3B—C10B—C11B	−178.7 (3)	N4B—C4B—C5B—C7B	−3.5 (4)
C6A—N1A—C2A—N3A	−0.7 (4)	C4B—C5B—C7B—C8B	−169.7 (2)
C6A—N1A—C2A—N2A	179.9 (2)	C4B—C5B—C6B—N1B	0.9 (4)
C2A—N1A—C6A—C5A	0.2 (4)	C7B—C5B—C6B—N1B	−178.2 (2)
C2A—N3A—C4A—C5A	−0.8 (4)	C6B—C5B—C7B—C8B	9.4 (4)
C4A—N3A—C2A—N2A	−179.7 (2)	C5B—C7B—C8B—C13B	79.7 (3)
C2A—N3A—C4A—N4A	−179.6 (2)	C5B—C7B—C8B—C9B	−100.7 (3)
C4A—N3A—C2A—N1A	0.9 (4)	C7B—C8B—C9B—C10B	−178.6 (3)
C6B—N1B—C2B—N2B	178.8 (2)	C13B—C8B—C9B—C10B	1.0 (4)
C2B—N1B—C6B—C5B	0.7 (4)	C7B—C8B—C13B—C12B	179.0 (3)
C6B—N1B—C2B—N3B	−1.3 (4)	C9B—C8B—C13B—C12B	−0.6 (4)
C2B—N3B—C4B—N4B	−177.8 (2)	C8B—C9B—C10B—C11B	−0.1 (4)
C2B—N3B—C4B—C5B	1.8 (4)	C8B—C9B—C10B—O3B	178.9 (3)
C4B—N3B—C2B—N1B	0.0 (4)	C9B—C10B—C11B—O2B	173.9 (2)
C4B—N3B—C2B—N2B	179.9 (2)	O3B—C10B—C11B—O2B	−5.1 (4)
C17—N5—C21—C22	−179.1 (2)	C9B—C10B—C11B—C12B	−1.1 (4)
C21—N5—C17—C18	1.2 (4)	O3B—C10B—C11B—C12B	179.8 (2)
C21—N5—C17—C23	−179.5 (2)	O2B—C11B—C12B—O1B	5.9 (4)
C17—N5—C21—C20	−0.3 (4)	C10B—C11B—C12B—C13B	1.4 (4)
N3A—C4A—C5A—C6A	0.3 (4)	O2B—C11B—C12B—C13B	−173.7 (2)
N4A—C4A—C5A—C6A	179.1 (2)	C10B—C11B—C12B—O1B	−179.1 (2)
N3A—C4A—C5A—C7A	176.7 (2)	C11B—C12B—C13B—C8B	−0.6 (4)
N4A—C4A—C5A—C7A	−4.5 (4)	O1B—C12B—C13B—C8B	180.0 (3)
C7A—C5A—C6A—N1A	−176.4 (2)	N5—C17—C18—C19	−1.0 (4)
C4A—C5A—C7A—C8A	159.9 (2)	C23—C17—C18—C19	179.7 (3)
C4A—C5A—C6A—N1A	0.0 (4)	N5—C17—C23—O4	−172.1 (2)
C6A—C5A—C7A—C8A	−24.0 (3)	N5—C17—C23—O5	6.6 (4)
C5A—C7A—C8A—C9A	−90.8 (3)	C18—C17—C23—O4	7.1 (4)
C5A—C7A—C8A—C13A	87.9 (3)	C18—C17—C23—O5	−174.2 (3)
C9A—C8A—C13A—C12A	0.6 (4)	C17—C18—C19—C20	0.0 (4)
C7A—C8A—C9A—C10A	177.7 (3)	C18—C19—C20—C21	0.8 (4)
C7A—C8A—C13A—C12A	−178.0 (3)	C19—C20—C21—N5	−0.7 (4)
C13A—C8A—C9A—C10A	−0.9 (4)	C19—C20—C21—C22	178.1 (3)
C8A—C9A—C10A—O3A	−179.6 (3)	N5—C21—C22—O6	11.1 (4)
C8A—C9A—C10A—C11A	0.2 (4)	N5—C21—C22—O7	−169.2 (2)
C9A—C10A—C11A—C12A	0.8 (4)	C20—C21—C22—O6	−167.8 (3)
O3A—C10A—C11A—C12A	−179.4 (3)	C20—C21—C22—O7	12.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O7ⁱ	0.99	1.75	2.730 (3)	168
N1B—H1B···O4Wⁱⁱ	0.92	1.81	2.728 (3)	176
N2A—H2A···O2Wⁱⁱⁱ	0.86	2.52	3.138 (4)	129
N2A—H2B···O6ⁱ	0.86	2.05	2.892 (3)	165
N4A—H4A···N3B^iv	0.86	2.26	3.113 (3)	174
N4A—H4B···O4	0.86	2.09	2.900 (3)	156
O1W—H11···O7^v	0.97	1.82	2.754 (4)	160
O1W—H12···O2W	0.98	1.76	2.712 (5)	165
O2W—H21···O3W	0.98	2.20	3.139 (4)	160
N2B—H21A···N3A^iv	0.86	2.16	3.009 (3)	170
O2W—H22···O5W^vi	0.86	2.51	2.976 (5)	114
N2B—H22B···O1Wⁱⁱ	0.86	2.50	3.265 (4)	149
O3W—H31···O6	0.95	1.90	2.854 (3)	178
O3W—H31···N5	0.95	2.52	2.898 (3)	104
O3W—H32···O5	0.94	1.85	2.759 (4)	162
O3W—H32···N5	0.94	2.40	2.898 (3)	113
O4W—H41···O1W	0.95	1.81	2.738 (3)	165
N4B—H41A···O5^iv	0.86	2.05	2.798 (3)	145
O4W—H42···O4	0.97	1.79	2.733 (3)	164
O5W—H51···O6^vii	0.93	2.00	2.821 (4)	146
O5W—H52···O3W^iv	0.96	1.69	2.594 (4)	155
C7A—H7B···O4	0.97	2.27	3.176 (3)	155
C13A—H13A···O5W	0.93	2.52	3.384 (4)	154
C16A—H16A···O2A^viii	0.96	2.38	3.061 (4)	128

Symmetry codes: (i) x−1, y−1, z; (ii) x+1, y, z; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z; (v) x−1, y, z; (vi) x, y+1, z; (vii) x, y−1, z; (viii) −x+1/2, y+1/2, −z+1/2.

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