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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020167/lh6416sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020167/lh6416Isup2.hkl
Contains datablock I

CCDC reference: 227940

Key indicators

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

checkCIF/PLATON results

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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+·C7H3NO42·5H2OF(000) = 1776
Mr = 837.85Dx = 1.338 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 9.713 (2) Åθ = 3.1–27.0°
b = 12.025 (3) ŵ = 0.11 mm1
c = 35.703 (3) ÅT = 293 K
β = 94.23 (3)°Block, colourless
V = 4158.7 (14) Å30.38 × 0.26 × 0.19 mm
Z = 4
Data collection top
Philips PW1100
diffractometer
4170 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.0°, θmin = 3.1°
ω scansh = 1212
Absorption correction: part of the refinement model (ΔF)
(SHELXA; Sheldrick, 1997)
k = 015
Tmin = 0.961, Tmax = 0.980l = 045
9210 measured reflections1 standard reflections every 100 reflections
9074 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.160 w = 1/[σ2(Fo2) + (0.0728P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
9074 reflectionsΔρmax = 0.33 e Å3
532 parametersΔρmin = 0.35 e Å3
6 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001Fc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
O1A0.5277 (2)0.00551 (17)0.19165 (6)0.0672 (9)
O2A0.4094 (2)0.12086 (17)0.24403 (5)0.0605 (8)
O3A0.2905 (2)0.31753 (18)0.22869 (6)0.0695 (9)
N1A0.0646 (2)0.10468 (17)0.05921 (6)0.0393 (7)
N2A0.0927 (2)0.11773 (18)0.00838 (6)0.0511 (8)
N3A0.0723 (2)0.25576 (16)0.01799 (5)0.0344 (7)
N4A0.2354 (2)0.39029 (17)0.02812 (6)0.0442 (8)
C2A0.0162 (3)0.1608 (2)0.02837 (7)0.0347 (8)
C4A0.1826 (3)0.2955 (2)0.03903 (7)0.0334 (8)
C5A0.2395 (2)0.2391 (2)0.07233 (7)0.0336 (8)
C6A0.1759 (3)0.1447 (2)0.08074 (7)0.0386 (9)
C7A0.3676 (3)0.2815 (2)0.09441 (7)0.0462 (10)
C8A0.3859 (3)0.2398 (2)0.13451 (7)0.0400 (9)
C9A0.3312 (3)0.3010 (2)0.16246 (8)0.0472 (10)
C10A0.3418 (3)0.2633 (2)0.19941 (8)0.0454 (10)
C11A0.4084 (3)0.1633 (2)0.20816 (7)0.0442 (10)
C12A0.4649 (3)0.1031 (2)0.18027 (8)0.0453 (10)
C13A0.4537 (3)0.1407 (2)0.14327 (8)0.0447 (10)
C14A0.5937 (4)0.0574 (3)0.16484 (11)0.0867 (16)
C15A0.5147 (4)0.1564 (4)0.26973 (10)0.114 (2)
C16A0.2072 (5)0.4124 (3)0.22065 (11)0.0974 (19)
O1B0.7765 (2)0.32451 (18)0.24788 (6)0.0674 (9)
O2B0.9412 (2)0.15273 (17)0.26471 (5)0.0626 (8)
O3B1.0566 (2)0.03647 (18)0.21136 (5)0.0655 (8)
N1B1.0298 (2)0.49072 (18)0.09778 (6)0.0449 (8)
N2B1.0387 (2)0.62059 (19)0.05104 (6)0.0560 (9)
N3B0.8715 (2)0.48534 (17)0.04479 (6)0.0385 (7)
N4B0.7097 (2)0.3467 (2)0.03922 (6)0.0540 (9)
C2B0.9785 (3)0.5318 (2)0.06421 (7)0.0396 (9)
C4B0.8136 (3)0.3949 (2)0.05933 (7)0.0373 (9)
C5B0.8611 (3)0.3493 (2)0.09539 (7)0.0384 (8)
C6B0.9700 (3)0.4009 (2)0.11283 (7)0.0433 (9)
C7B0.7899 (3)0.2514 (2)0.11187 (7)0.0516 (10)
C8B0.8360 (3)0.2267 (2)0.15255 (7)0.0448 (10)
C9B0.9283 (3)0.1426 (2)0.16177 (7)0.0470 (10)
C10B0.9676 (3)0.1193 (2)0.19951 (8)0.0473 (10)
C11B0.9136 (3)0.1812 (2)0.22763 (7)0.0458 (10)
C12B0.8221 (3)0.2677 (2)0.21819 (8)0.0480 (10)
C13B0.7837 (3)0.2893 (2)0.18068 (8)0.0500 (10)
C14B0.6886 (4)0.4174 (3)0.24005 (11)0.0920 (17)
C15B1.0629 (4)0.2001 (4)0.28273 (9)0.0872 (18)
C16B1.1173 (4)0.0281 (3)0.18386 (9)0.0710 (12)
O40.4128 (2)0.53599 (18)0.07495 (6)0.0751 (9)
O50.4573 (3)0.6459 (2)0.02803 (6)0.0944 (10)
O60.7868 (2)0.93134 (16)0.04534 (6)0.0609 (8)
O70.9608 (2)0.91555 (16)0.08868 (6)0.0614 (8)
N50.6698 (2)0.74232 (17)0.07016 (6)0.0406 (8)
C170.6045 (3)0.6553 (2)0.08396 (7)0.0405 (9)
C180.6446 (3)0.6100 (2)0.11861 (8)0.0543 (11)
C190.7564 (3)0.6547 (3)0.13928 (9)0.0710 (12)
C200.8249 (3)0.7431 (2)0.12482 (8)0.0581 (11)
C210.7787 (3)0.7855 (2)0.09025 (7)0.0387 (9)
C220.8465 (3)0.8847 (2)0.07334 (8)0.0448 (10)
C230.4821 (3)0.6087 (2)0.05994 (8)0.0526 (11)
O1W0.2018 (3)0.8005 (2)0.10661 (10)0.1239 (14)
O2W0.3449 (3)0.8911 (3)0.05177 (9)0.1569 (19)
O3W0.5736 (3)0.8311 (2)0.00256 (6)0.0884 (10)
O4W0.2566 (2)0.59006 (18)0.13290 (6)0.0746 (9)
O5W0.5593 (4)0.0682 (3)0.05840 (7)0.191 (2)
H1A0.020700.034400.066600.0470*
H2A0.127000.151300.011400.0610*
H2B0.128500.056400.015300.0610*
H4A0.199200.423700.008500.0530*
H4B0.305800.418700.040700.0530*
H6A0.208600.104900.101900.0460*
H7A0.447800.260100.081400.0550*
H7B0.364300.362100.094800.0550*
H9A0.287400.368200.156600.0570*
H13A0.491700.099500.124500.0540*
H14A0.526300.083300.145800.1040*
H14B0.639600.119900.176900.1040*
H14C0.660100.011500.153600.1040*
H15A0.601700.129700.262300.1360*
H15B0.499200.127900.294200.1360*
H15C0.515900.236200.270500.1360*
H16A0.172100.439400.243400.1170*
H16B0.261700.469400.210000.1170*
H16C0.131600.393000.203100.1170*
H1B1.104000.523700.110700.0540*
H6B1.005800.374400.136000.0520*
H9B0.964500.101000.142800.0560*
H13B0.722300.346800.174400.0600*
H21A1.008700.648500.029800.0670*
H22B1.107900.650400.063700.0670*
H41A0.681400.373500.017700.0650*
H42B0.670600.288800.047700.0650*
H71A0.691200.264900.110000.0620*
H72B0.806600.186000.096900.0620*
H1410.605500.393200.226200.1100*
H1420.665900.451000.263200.1100*
H1430.735100.470700.225400.1100*
H1511.056100.279800.282000.1050*
H1521.073400.175800.308400.1050*
H1531.141400.176800.269900.1050*
H1611.172100.019000.169100.0850*
H1621.175000.084300.196000.0850*
H1631.046200.062800.167800.0850*
H180.596800.550100.127800.0650*
H190.785100.625600.162700.0850*
H200.901400.773900.138200.0700*
H110.114200.840000.106300.1490*
H120.246500.823100.084200.1490*
H210.409900.889400.032000.1880*
H220.399200.910400.070900.1880*
H310.643400.866300.013300.1060*
H320.553600.763300.009000.1060*
H410.237600.666300.128100.0900*
H420.324800.567900.115900.0900*
H510.649100.051800.052700.2290*
H520.531600.118700.038500.2290*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0868 (17)0.0504 (13)0.0635 (14)0.0228 (12)0.0002 (12)0.0160 (11)
O2A0.0708 (14)0.0649 (14)0.0439 (12)0.0100 (12)0.0090 (10)0.0170 (10)
O3A0.0898 (17)0.0680 (15)0.0491 (13)0.0187 (13)0.0057 (12)0.0093 (11)
N1A0.0417 (13)0.0311 (11)0.0440 (13)0.0125 (10)0.0045 (10)0.0082 (10)
N2A0.0534 (15)0.0409 (13)0.0559 (15)0.0194 (12)0.0173 (12)0.0110 (11)
N3A0.0366 (12)0.0318 (12)0.0339 (12)0.0088 (10)0.0038 (9)0.0043 (9)
N4A0.0468 (14)0.0385 (13)0.0448 (13)0.0148 (11)0.0131 (11)0.0147 (11)
C2A0.0335 (15)0.0324 (14)0.0371 (15)0.0044 (12)0.0040 (12)0.0007 (12)
C4A0.0342 (15)0.0296 (14)0.0361 (14)0.0043 (11)0.0014 (11)0.0023 (11)
C5A0.0333 (14)0.0318 (14)0.0350 (14)0.0051 (11)0.0019 (11)0.0038 (11)
C6A0.0393 (15)0.0380 (15)0.0374 (15)0.0048 (12)0.0048 (12)0.0074 (12)
C7A0.0446 (17)0.0481 (17)0.0439 (16)0.0168 (14)0.0105 (13)0.0100 (13)
C8A0.0392 (15)0.0390 (15)0.0398 (15)0.0123 (13)0.0112 (12)0.0078 (13)
C9A0.0493 (18)0.0375 (16)0.0519 (18)0.0009 (13)0.0162 (14)0.0040 (14)
C10A0.0515 (18)0.0408 (16)0.0422 (16)0.0023 (14)0.0087 (14)0.0046 (13)
C11A0.0512 (18)0.0424 (16)0.0372 (16)0.0099 (14)0.0089 (13)0.0065 (13)
C12A0.0470 (17)0.0351 (15)0.0518 (18)0.0037 (13)0.0093 (14)0.0102 (14)
C13A0.0427 (16)0.0459 (17)0.0447 (17)0.0030 (13)0.0014 (13)0.0010 (13)
C14A0.104 (3)0.061 (2)0.095 (3)0.031 (2)0.007 (2)0.005 (2)
C15A0.108 (3)0.169 (5)0.057 (2)0.037 (3)0.038 (2)0.040 (3)
C16A0.128 (4)0.078 (3)0.085 (3)0.043 (3)0.001 (2)0.013 (2)
O1B0.0795 (17)0.0653 (15)0.0582 (13)0.0089 (13)0.0113 (12)0.0081 (12)
O2B0.0795 (16)0.0689 (14)0.0385 (12)0.0060 (12)0.0023 (11)0.0100 (10)
O3B0.0817 (16)0.0663 (14)0.0482 (13)0.0212 (13)0.0031 (11)0.0086 (11)
N1B0.0408 (13)0.0534 (14)0.0382 (13)0.0131 (11)0.0127 (10)0.0094 (11)
N2B0.0597 (17)0.0536 (16)0.0512 (15)0.0206 (13)0.0188 (12)0.0173 (12)
N3B0.0387 (13)0.0381 (12)0.0374 (12)0.0026 (10)0.0069 (10)0.0052 (10)
N4B0.0541 (15)0.0638 (16)0.0413 (14)0.0189 (13)0.0156 (12)0.0109 (12)
C2B0.0430 (16)0.0360 (15)0.0387 (15)0.0005 (13)0.0049 (13)0.0061 (12)
C4B0.0334 (15)0.0411 (15)0.0367 (15)0.0015 (12)0.0029 (12)0.0004 (12)
C5B0.0377 (15)0.0422 (15)0.0345 (14)0.0032 (13)0.0035 (12)0.0066 (12)
C6B0.0385 (16)0.0514 (17)0.0385 (15)0.0063 (14)0.0075 (13)0.0153 (13)
C7B0.0490 (18)0.0616 (19)0.0423 (16)0.0147 (15)0.0088 (13)0.0138 (14)
C8B0.0439 (17)0.0499 (17)0.0398 (16)0.0138 (14)0.0021 (13)0.0102 (14)
C9B0.0516 (18)0.0540 (18)0.0358 (16)0.0078 (15)0.0062 (13)0.0035 (13)
C10B0.0525 (18)0.0447 (17)0.0446 (17)0.0018 (15)0.0022 (14)0.0097 (14)
C11B0.0512 (18)0.0499 (18)0.0359 (16)0.0093 (15)0.0013 (13)0.0047 (14)
C12B0.0495 (18)0.0489 (18)0.0460 (17)0.0095 (15)0.0059 (14)0.0020 (15)
C13B0.0463 (18)0.0449 (17)0.0580 (19)0.0041 (14)0.0018 (15)0.0108 (15)
C14B0.110 (3)0.069 (3)0.098 (3)0.023 (2)0.015 (2)0.015 (2)
C15B0.076 (3)0.131 (4)0.052 (2)0.000 (2)0.0129 (19)0.000 (2)
C16B0.075 (2)0.070 (2)0.067 (2)0.0151 (19)0.0024 (18)0.0040 (19)
O40.0862 (16)0.0642 (15)0.0711 (15)0.0495 (13)0.0196 (12)0.0097 (12)
O50.0996 (19)0.115 (2)0.0612 (15)0.0632 (16)0.0438 (14)0.0330 (14)
O60.0489 (12)0.0547 (13)0.0771 (15)0.0112 (10)0.0081 (11)0.0288 (11)
O70.0463 (13)0.0520 (13)0.0828 (15)0.0236 (10)0.0154 (11)0.0167 (11)
N50.0409 (13)0.0374 (13)0.0421 (13)0.0105 (11)0.0063 (10)0.0072 (10)
C170.0417 (16)0.0346 (15)0.0436 (16)0.0086 (13)0.0072 (13)0.0070 (12)
C180.0538 (19)0.0512 (18)0.0553 (18)0.0209 (15)0.0137 (15)0.0212 (15)
C190.070 (2)0.081 (2)0.057 (2)0.031 (2)0.0293 (17)0.0345 (18)
C200.0515 (19)0.059 (2)0.060 (2)0.0250 (16)0.0210 (15)0.0136 (16)
C210.0364 (15)0.0335 (14)0.0450 (16)0.0069 (12)0.0060 (12)0.0046 (12)
C220.0381 (16)0.0338 (15)0.0619 (19)0.0033 (13)0.0005 (14)0.0070 (14)
C230.056 (2)0.0489 (18)0.0502 (18)0.0206 (16)0.0146 (15)0.0061 (15)
O1W0.0790 (19)0.092 (2)0.202 (3)0.0165 (16)0.019 (2)0.044 (2)
O2W0.096 (2)0.275 (5)0.103 (2)0.060 (3)0.0299 (18)0.016 (3)
O3W0.117 (2)0.0767 (16)0.0662 (15)0.0053 (15)0.0280 (14)0.0202 (13)
O4W0.0626 (14)0.0759 (16)0.0816 (16)0.0211 (12)0.0200 (12)0.0070 (13)
O5W0.216 (4)0.288 (5)0.0641 (18)0.185 (4)0.022 (2)0.027 (2)
Geometric parameters (Å, º) top
O1A—C12A1.370 (3)C8A—C9A1.378 (4)
O1A—C14A1.411 (4)C8A—C13A1.386 (4)
O2A—C11A1.378 (3)C9A—C10A1.392 (4)
O2A—C15A1.390 (4)C10A—C11A1.390 (4)
O3A—C10A1.358 (3)C11A—C12A1.377 (4)
O3A—C16A1.416 (5)C12A—C13A1.393 (4)
N1A—C2A1.346 (3)C6A—H6A0.9302
N1A—C6A1.367 (3)C7A—H7B0.9699
N2A—C2A1.336 (3)C7A—H7A0.9707
N3A—C4A1.350 (3)C9A—H9A0.9299
N3A—C2A1.330 (3)C13A—H13A0.9313
N4A—C4A1.320 (3)C14A—H14B0.9595
O1B—C12B1.362 (3)C14A—H14A0.9602
O1B—C14B1.421 (4)C14A—H14C0.9591
O2B—C15B1.422 (4)C15A—H15A0.9595
O2B—C11B1.375 (3)C15A—H15C0.9600
O3B—C10B1.365 (3)C15A—H15B0.9606
O3B—C16B1.414 (4)C16A—H16B0.9614
N1B—C2B1.357 (3)C16A—H16C0.9583
N1B—C6B1.356 (3)C16A—H16A0.9603
N2B—C2B1.320 (3)C4B—C5B1.443 (4)
N3B—C2B1.329 (3)C5B—C7B1.507 (4)
N3B—C4B1.346 (3)C5B—C6B1.340 (4)
N4B—C4B1.328 (3)C7B—C8B1.517 (4)
O4—C231.248 (3)C8B—C9B1.375 (4)
O5—C231.231 (4)C8B—C13B1.382 (4)
O6—C221.251 (3)C9B—C10B1.401 (4)
O7—C221.257 (3)C10B—C11B1.384 (4)
N5—C211.338 (3)C11B—C12B1.393 (4)
N5—C171.336 (3)C12B—C13B1.388 (4)
O1W—H120.9766C6B—H6B0.9297
O1W—H110.9738C7B—H72B0.9712
O2W—H210.9813C7B—H71A0.9698
O2W—H220.8634C9B—H9B0.9315
N1A—H1A0.9911C13B—H13B0.9297
N2A—H2A0.8591C14B—H1410.9601
N2A—H2B0.8594C14B—H1430.9608
O3W—H310.9502C14B—H1420.9602
O3W—H320.9405C15B—H1530.9598
N4A—H4A0.8599C15B—H1520.9602
N4A—H4B0.8606C15B—H1510.9609
N1B—H1B0.9168C16B—H1610.9608
N2B—H21A0.8602C16B—H1620.9606
N2B—H22B0.8601C16B—H1630.9599
N4B—H41A0.8594C17—C181.381 (4)
N4B—H42B0.8588C17—C231.521 (4)
O4W—H420.9683C18—C191.376 (4)
O4W—H410.9483C19—C201.375 (4)
O5W—H520.9580C20—C211.379 (4)
O5W—H510.9313C21—C221.510 (4)
C4A—C5A1.443 (4)C18—H180.9298
C5A—C6A1.337 (3)C19—H190.9300
C5A—C7A1.512 (4)C20—H200.9301
C7A—C8A1.515 (4)
C12A—O1A—C14A118.2 (2)N1A—C6A—H6A118.95
C11A—O2A—C15A117.0 (2)C8A—C7A—H7A108.79
C10A—O3A—C16A117.9 (2)H7A—C7A—H7B107.48
C2A—N1A—C6A119.8 (2)C5A—C7A—H7A108.65
C2A—N3A—C4A118.3 (2)C5A—C7A—H7B108.53
N1A—C2A—N3A122.2 (2)C8A—C7A—H7B108.60
N2A—C2A—N3A120.6 (2)C10A—C9A—H9A119.81
N1A—C2A—N2A117.2 (2)C8A—C9A—H9A119.72
N3A—C4A—C5A122.2 (2)C8A—C13A—H13A120.13
N4A—C4A—C5A121.0 (2)C12A—C13A—H13A120.16
N3A—C4A—N4A116.8 (2)H14A—C14A—H14B109.49
N1A—C6A—C5A122.1 (2)O1A—C14A—H14C109.18
O3A—C10A—C9A124.6 (2)H14A—C14A—H14C109.56
O3A—C10A—C11A115.7 (2)O1A—C14A—H14A109.52
O2A—C11A—C10A120.0 (2)O1A—C14A—H14B109.57
O2A—C11A—C12A120.1 (2)H14B—C14A—H14C109.51
O1A—C12A—C13A124.1 (2)H15B—C15A—H15C109.45
O1A—C12A—C11A115.3 (2)H15A—C15A—H15B109.41
C12B—O1B—C14B117.8 (2)H15A—C15A—H15C109.47
C11B—O2B—C15B115.6 (2)O2A—C15A—H15C109.45
C10B—O3B—C16B118.2 (2)O2A—C15A—H15B109.49
C2B—N1B—C6B120.0 (2)O2A—C15A—H15A109.56
C2B—N3B—C4B118.1 (2)H16B—C16A—H16C109.43
N1B—C2B—N3B122.0 (2)O3A—C16A—H16A109.52
N2B—C2B—N3B120.3 (2)H16A—C16A—H16C109.43
N1B—C2B—N2B117.7 (2)O3A—C16A—H16C109.59
N4B—C4B—C5B119.8 (2)H16A—C16A—H16B109.49
N3B—C4B—C5B122.4 (2)O3A—C16A—H16B109.36
N3B—C4B—N4B117.8 (2)C4B—C5B—C7B121.3 (2)
N1B—C6B—C5B122.1 (2)C4B—C5B—C6B115.3 (2)
O3B—C10B—C9B124.4 (2)C6B—C5B—C7B123.4 (2)
O3B—C10B—C11B115.6 (2)C5B—C7B—C8B114.5 (2)
O2B—C11B—C12B119.6 (2)C7B—C8B—C9B120.9 (2)
O2B—C11B—C10B120.5 (2)C7B—C8B—C13B119.4 (2)
O1B—C12B—C13B125.3 (2)C9B—C8B—C13B119.7 (2)
O1B—C12B—C11B115.1 (2)C8B—C9B—C10B120.2 (2)
C17—N5—C21118.9 (2)C9B—C10B—C11B119.9 (2)
N5—C17—C18121.9 (2)C10B—C11B—C12B119.7 (2)
N5—C17—C23116.9 (2)C11B—C12B—C13B119.6 (2)
N5—C21—C20121.9 (2)C8B—C13B—C12B120.8 (2)
N5—C21—C22116.3 (2)C5B—C6B—H6B119.05
O7—C22—C21117.1 (2)N1B—C6B—H6B118.85
O6—C22—C21118.9 (2)C5B—C7B—H72B108.52
O6—C22—O7123.9 (2)C8B—C7B—H71A108.61
O4—C23—C17116.1 (2)C5B—C7B—H71A108.80
O4—C23—O5125.2 (3)C8B—C7B—H72B108.59
O5—C23—C17118.7 (3)H71A—C7B—H72B107.58
H11—O1W—H12107.21C10B—C9B—H9B120.07
H21—O2W—H22100.76C8B—C9B—H9B119.68
C6A—N1A—H1A119.24C8B—C13B—H13B119.58
C2A—N1A—H1A120.93C12B—C13B—H13B119.59
H2A—N2A—H2B119.93O1B—C14B—H141109.46
C2A—N2A—H2A120.05O1B—C14B—H142109.52
C2A—N2A—H2B120.02H141—C14B—H143109.44
H31—O3W—H32106.62O1B—C14B—H143109.37
C4A—N4A—H4B119.98H142—C14B—H143109.57
C4A—N4A—H4A119.95H141—C14B—H142109.46
H4A—N4A—H4B120.07O2B—C15B—H152109.64
C6B—N1B—H1B119.28O2B—C15B—H153109.28
C2B—N1B—H1B120.72O2B—C15B—H151109.51
C2B—N2B—H21A119.95H152—C15B—H153109.54
C2B—N2B—H22B119.95H151—C15B—H153109.49
H21A—N2B—H22B120.09H151—C15B—H152109.37
C4B—N4B—H41A120.00O3B—C16B—H163109.57
H41A—N4B—H42B119.91H161—C16B—H162109.50
C4B—N4B—H42B120.10H162—C16B—H163109.50
H41—O4W—H42106.61O3B—C16B—H161109.47
H51—O5W—H52100.87H161—C16B—H163109.38
C6A—C5A—C7A123.1 (2)O3B—C16B—H162109.40
C4A—C5A—C7A121.4 (2)C18—C17—C23121.1 (2)
C4A—C5A—C6A115.4 (2)C17—C18—C19119.0 (3)
C5A—C7A—C8A114.6 (2)C18—C19—C20119.0 (3)
C7A—C8A—C9A118.9 (2)C19—C20—C21119.2 (3)
C9A—C8A—C13A119.9 (2)C20—C21—C22121.8 (2)
C7A—C8A—C13A121.2 (2)C17—C18—H18120.43
C8A—C9A—C10A120.5 (2)C19—C18—H18120.53
C9A—C10A—C11A119.7 (2)C20—C19—H19120.48
C10A—C11A—C12A119.7 (2)C18—C19—H19120.49
C11A—C12A—C13A120.5 (2)C21—C20—H20120.48
C8A—C13A—C12A119.7 (2)C19—C20—H20120.36
C5A—C6A—H6A118.91
C14A—O1A—C12A—C11A176.9 (3)O3A—C10A—C11A—O2A5.2 (4)
C14A—O1A—C12A—C13A4.6 (4)C9A—C10A—C11A—O2A174.6 (3)
C15A—O2A—C11A—C10A87.2 (4)C10A—C11A—C12A—C13A1.1 (4)
C15A—O2A—C11A—C12A97.3 (3)O2A—C11A—C12A—C13A174.3 (3)
C16A—O3A—C10A—C9A7.4 (4)C10A—C11A—C12A—O1A179.7 (2)
C16A—O3A—C10A—C11A172.4 (3)O2A—C11A—C12A—O1A4.2 (4)
C14B—O1B—C12B—C13B3.7 (4)O1A—C12A—C13A—C8A178.8 (3)
C14B—O1B—C12B—C11B176.8 (3)C11A—C12A—C13A—C8A0.4 (4)
C15B—O2B—C11B—C12B96.6 (3)N4B—C4B—C5B—C6B177.3 (2)
C15B—O2B—C11B—C10B88.3 (3)N3B—C4B—C5B—C6B2.2 (4)
C16B—O3B—C10B—C9B2.3 (4)N3B—C4B—C5B—C7B176.9 (2)
C16B—O3B—C10B—C11B178.7 (3)N4B—C4B—C5B—C7B3.5 (4)
C6A—N1A—C2A—N3A0.7 (4)C4B—C5B—C7B—C8B169.7 (2)
C6A—N1A—C2A—N2A179.9 (2)C4B—C5B—C6B—N1B0.9 (4)
C2A—N1A—C6A—C5A0.2 (4)C7B—C5B—C6B—N1B178.2 (2)
C2A—N3A—C4A—C5A0.8 (4)C6B—C5B—C7B—C8B9.4 (4)
C4A—N3A—C2A—N2A179.7 (2)C5B—C7B—C8B—C13B79.7 (3)
C2A—N3A—C4A—N4A179.6 (2)C5B—C7B—C8B—C9B100.7 (3)
C4A—N3A—C2A—N1A0.9 (4)C7B—C8B—C9B—C10B178.6 (3)
C6B—N1B—C2B—N2B178.8 (2)C13B—C8B—C9B—C10B1.0 (4)
C2B—N1B—C6B—C5B0.7 (4)C7B—C8B—C13B—C12B179.0 (3)
C6B—N1B—C2B—N3B1.3 (4)C9B—C8B—C13B—C12B0.6 (4)
C2B—N3B—C4B—N4B177.8 (2)C8B—C9B—C10B—C11B0.1 (4)
C2B—N3B—C4B—C5B1.8 (4)C8B—C9B—C10B—O3B178.9 (3)
C4B—N3B—C2B—N1B0.0 (4)C9B—C10B—C11B—O2B173.9 (2)
C4B—N3B—C2B—N2B179.9 (2)O3B—C10B—C11B—O2B5.1 (4)
C17—N5—C21—C22179.1 (2)C9B—C10B—C11B—C12B1.1 (4)
C21—N5—C17—C181.2 (4)O3B—C10B—C11B—C12B179.8 (2)
C21—N5—C17—C23179.5 (2)O2B—C11B—C12B—O1B5.9 (4)
C17—N5—C21—C200.3 (4)C10B—C11B—C12B—C13B1.4 (4)
N3A—C4A—C5A—C6A0.3 (4)O2B—C11B—C12B—C13B173.7 (2)
N4A—C4A—C5A—C6A179.1 (2)C10B—C11B—C12B—O1B179.1 (2)
N3A—C4A—C5A—C7A176.7 (2)C11B—C12B—C13B—C8B0.6 (4)
N4A—C4A—C5A—C7A4.5 (4)O1B—C12B—C13B—C8B180.0 (3)
C7A—C5A—C6A—N1A176.4 (2)N5—C17—C18—C191.0 (4)
C4A—C5A—C7A—C8A159.9 (2)C23—C17—C18—C19179.7 (3)
C4A—C5A—C6A—N1A0.0 (4)N5—C17—C23—O4172.1 (2)
C6A—C5A—C7A—C8A24.0 (3)N5—C17—C23—O56.6 (4)
C5A—C7A—C8A—C9A90.8 (3)C18—C17—C23—O47.1 (4)
C5A—C7A—C8A—C13A87.9 (3)C18—C17—C23—O5174.2 (3)
C9A—C8A—C13A—C12A0.6 (4)C17—C18—C19—C200.0 (4)
C7A—C8A—C9A—C10A177.7 (3)C18—C19—C20—C210.8 (4)
C7A—C8A—C13A—C12A178.0 (3)C19—C20—C21—N50.7 (4)
C13A—C8A—C9A—C10A0.9 (4)C19—C20—C21—C22178.1 (3)
C8A—C9A—C10A—O3A179.6 (3)N5—C21—C22—O611.1 (4)
C8A—C9A—C10A—C11A0.2 (4)N5—C21—C22—O7169.2 (2)
C9A—C10A—C11A—C12A0.8 (4)C20—C21—C22—O6167.8 (3)
O3A—C10A—C11A—C12A179.4 (3)C20—C21—C22—O712.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O7i0.991.752.730 (3)168
N1B—H1B···O4Wii0.921.812.728 (3)176
N2A—H2A···O2Wiii0.862.523.138 (4)129
N2A—H2B···O6i0.862.052.892 (3)165
N4A—H4A···N3Biv0.862.263.113 (3)174
N4A—H4B···O40.862.092.900 (3)156
O1W—H11···O7v0.971.822.754 (4)160
O1W—H12···O2W0.981.762.712 (5)165
O2W—H21···O3W0.982.203.139 (4)160
N2B—H21A···N3Aiv0.862.163.009 (3)170
O2W—H22···O5Wvi0.862.512.976 (5)114
N2B—H22B···O1Wii0.862.503.265 (4)149
O3W—H31···O60.951.902.854 (3)178
O3W—H31···N50.952.522.898 (3)104
O3W—H32···O50.941.852.759 (4)162
O3W—H32···N50.942.402.898 (3)113
O4W—H41···O1W0.951.812.738 (3)165
N4B—H41A···O5iv0.862.052.798 (3)145
O4W—H42···O40.971.792.733 (3)164
O5W—H51···O6vii0.932.002.821 (4)146
O5W—H52···O3Wiv0.961.692.594 (4)155
C7A—H7B···O40.972.273.176 (3)155
C13A—H13A···O5W0.932.523.384 (4)154
C16A—H16A···O2Aviii0.962.383.061 (4)128
Symmetry codes: (i) x1, y1, z; (ii) x+1, y, z; (iii) x, y+1, z; (iv) x+1, y+1, z; (v) x1, y, z; (vi) x, y+1, z; (vii) x, y1, z; (viii) x+1/2, y+1/2, z+1/2.
 

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