Trimethyl-ammonium 5-(2,4-dinitro-phenyl)-2,6-dioxo-1,2,3,6-tetra-hydro-pyrimidin-4-olate 0.125-hydrate.

The asymmetric unit of the title salt C3H10N(+)·C10H5N4O7 (-)·0.125H2O [trivial name: trimethyl-ammonium 5-(2,4-dinitro-phen-yl)barbiturate 0.125-hydrate], contains two independent cations, two independent anions and a 0.25-occupancy solvent water mol-ecule. In one of the cations, the C atoms are disordered over two sets of sites with refined occupancies of 0.538 (8) and 0.462 (8). In the anions, the dihedral angles between the pyrimidine and benzene rings are 42.77 (6) and 46.55 (7)°. In the crystal, N-H⋯O hydrogen bonds connect anions and cations into chains along [010]. Within these chains, R 2 (2)(8) ring motifs are formed by inversion-related barbiturate anions. The H atoms of the partial occupancy water mol-ecule were not located nor included in the refinement.

Related literature

For the different types of anionic sigma complexes, see: Terrier (1982 ▶); Al-Kaysi et al. (2005 ▶). For the utility of spiro Meisenheimer complexes, see: Gallardo et al. (2007 ▶); Al-Kaysi et al. 2008 ▶). For the biological activity of carbanionic sigma complexes related to the title compound, see: Kalaivani et al. (2008 ▶); Kalaivani & Buvaneswari (2010 ▶). For the crystal structures of related barbiturates, see: Kalaivani & Malarvizhi (2009 ▶); Kalaivani et al. (2012 ▶). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C3H10N+·C10H5N4O7 −·0.125H2O

M = 355.29

Monoclinic,

a = 15.0410 (5) Å

b = 10.5460 (3) Å

c = 20.4170 (8) Å

β = 94.953 (1)°

V = 3226.50 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.960, T max = 0.987

26803 measured reflections

5517 independent reflections

3780 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.130

S = 1.02

5517 reflections

516 parameters

36 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006) ▶; software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007915/lh5595sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007915/lh5595Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007915/lh5595Isup3.cml

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

C3H10N+·C10H5N4O7−·0.125H2O	F(000) = 1482
Mr = 355.29	Dx = 1.464 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7398 reflections
a = 15.0410 (5) Å	θ = 2.3–23.9°
b = 10.5460 (3) Å	µ = 0.12 mm−1
c = 20.4170 (8) Å	T = 293 K
β = 94.953 (1)°	Needle, red
V = 3226.50 (19) Å3	0.30 × 0.20 × 0.20 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	5517 independent reflections
Radiation source: fine-focus sealed tube	3780 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω and φ scans	θmax = 24.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −17→17
Tmin = 0.960, Tmax = 0.987	k = −12→12
26803 measured reflections	l = −24→23

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0564P)2 + 1.2781P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
5517 reflections	Δρmax = 0.21 e Å−3
516 parameters	Δρmin = −0.21 e Å−3
36 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (4)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
C1	0.49436 (14)	0.3608 (2)	0.41756 (12)	0.0407 (5)
C2	0.34407 (14)	0.3929 (2)	0.36471 (11)	0.0397 (5)
C3	0.33767 (13)	0.26371 (19)	0.34916 (11)	0.0375 (5)
C4	0.40782 (14)	0.18045 (19)	0.37118 (11)	0.0373 (5)
C5	0.25811 (14)	0.2167 (2)	0.31023 (11)	0.0412 (5)
C6	0.17278 (15)	0.2572 (2)	0.32317 (13)	0.0508 (6)
H6	0.1672	0.3167	0.3562	0.061*
C7	0.09634 (16)	0.2114 (3)	0.28831 (15)	0.0630 (8)
H7	0.0406	0.2431	0.2962	0.076*
C8	0.10415 (18)	0.1187 (3)	0.24204 (14)	0.0611 (8)
C9	0.18518 (19)	0.0769 (3)	0.22658 (13)	0.0603 (7)
H9	0.1895	0.0146	0.1947	0.072*
C10	0.26101 (15)	0.1286 (2)	0.25901 (12)	0.0472 (6)
C11	0.48116 (14)	0.24816 (19)	0.58140 (11)	0.0399 (5)
C12	0.38713 (14)	0.06518 (19)	0.54816 (11)	0.0382 (5)
C13	0.31760 (13)	0.14908 (19)	0.52559 (11)	0.0376 (5)
C14	0.33028 (13)	0.28091 (19)	0.53044 (11)	0.0389 (5)
C15	0.23348 (14)	0.1023 (2)	0.49394 (12)	0.0422 (6)
C16	0.23265 (17)	0.0110 (2)	0.44466 (13)	0.0525 (6)
H16	0.2862	−0.0268	0.4359	0.063*
C17	0.1550 (2)	−0.0257 (2)	0.40826 (14)	0.0646 (8)
H17	0.1562	−0.0876	0.3759	0.077*
C18	0.07617 (18)	0.0312 (3)	0.42094 (16)	0.0675 (9)
C19	0.07232 (17)	0.1193 (3)	0.46899 (16)	0.0670 (8)
H19	0.0183	0.1569	0.4769	0.080*
C20	0.14985 (15)	0.1520 (2)	0.50569 (14)	0.0530 (7)
C21	0.2649 (2)	0.6911 (3)	0.4683 (2)	0.0951 (12)
H21A	0.2330	0.7699	0.4647	0.143*
H21B	0.2811	0.6660	0.4257	0.143*
H21C	0.3179	0.7012	0.4976	0.143*
C22	0.1287 (2)	0.5725 (3)	0.44899 (19)	0.0935 (11)
H22A	0.0955	0.5024	0.4643	0.140*
H22B	0.1462	0.5540	0.4059	0.140*
H22C	0.0921	0.6473	0.4472	0.140*
C23	0.1874 (4)	0.6194 (5)	0.5611 (2)	0.1438 (19)
H23A	0.1611	0.7020	0.5632	0.216*
H23B	0.2412	0.6162	0.5901	0.216*
H23C	0.1462	0.5567	0.5743	0.216*
N1	0.48201 (12)	0.23460 (17)	0.40610 (10)	0.0400 (5)
N2	0.42297 (12)	0.43476 (18)	0.39760 (10)	0.0450 (5)
N3	0.34457 (16)	0.0974 (2)	0.23077 (11)	0.0627 (6)
N4	0.0238 (2)	0.0651 (3)	0.20626 (16)	0.0905 (9)
N5	0.46542 (12)	0.12161 (16)	0.57581 (10)	0.0411 (5)
N6	0.41223 (12)	0.32321 (17)	0.55772 (10)	0.0412 (5)
N7	0.13846 (15)	0.2384 (2)	0.56078 (15)	0.0695 (7)
N8	−0.0066 (2)	−0.0018 (4)	0.38078 (18)	0.0998 (11)
N9	0.20830 (14)	0.5938 (2)	0.49399 (12)	0.0585 (6)
N10	0.31143 (19)	0.5901 (3)	0.23666 (15)	0.0822 (8)
C24	0.3960 (6)	0.6339 (15)	0.2289 (5)	0.139 (4)	0.538 (8)
H24A	0.4118	0.6979	0.2612	0.208*	0.538 (8)
H24B	0.3975	0.6694	0.1857	0.208*	0.538 (8)
H24C	0.4376	0.5650	0.2343	0.208*	0.538 (8)
C25	0.2718 (9)	0.4906 (11)	0.1921 (8)	0.100 (3)	0.538 (8)
H25A	0.2127	0.4713	0.2035	0.149*	0.538 (8)
H25B	0.3080	0.4156	0.1963	0.149*	0.538 (8)
H25C	0.2690	0.5204	0.1475	0.149*	0.538 (8)
C26	0.2437 (8)	0.7042 (9)	0.2306 (6)	0.166 (5)	0.538 (8)
H26A	0.1848	0.6738	0.2367	0.249*	0.538 (8)
H26B	0.2439	0.7417	0.1878	0.249*	0.538 (8)
H26C	0.2609	0.7665	0.2635	0.249*	0.538 (8)
C24'	0.4071 (5)	0.5293 (11)	0.2295 (5)	0.099 (3)	0.462 (8)
H24D	0.4483	0.5583	0.2649	0.149*	0.462 (8)
H24E	0.4278	0.5545	0.1883	0.149*	0.462 (8)
H24F	0.4027	0.4386	0.2311	0.149*	0.462 (8)
C25'	0.2503 (10)	0.5448 (16)	0.1872 (11)	0.133 (6)	0.462 (8)
H25D	0.2447	0.4546	0.1913	0.200*	0.462 (8)
H25E	0.2707	0.5648	0.1451	0.200*	0.462 (8)
H25F	0.1933	0.5839	0.1909	0.200*	0.462 (8)
C26'	0.3305 (12)	0.7243 (9)	0.2384 (7)	0.158 (5)	0.462 (8)
H26D	0.3714	0.7431	0.2758	0.238*	0.462 (8)
H26E	0.2761	0.7708	0.2414	0.238*	0.462 (8)
H26F	0.3567	0.7484	0.1989	0.238*	0.462 (8)
O1	0.56366 (10)	0.40504 (14)	0.44398 (9)	0.0549 (5)
O2	0.28668 (10)	0.47693 (14)	0.34922 (9)	0.0503 (4)
O3	0.40882 (10)	0.06395 (13)	0.36237 (8)	0.0474 (4)
O4	0.03283 (18)	−0.0250 (3)	0.16961 (14)	0.1164 (10)
O5	−0.04734 (18)	0.1135 (3)	0.21523 (16)	0.1303 (11)
O6	0.35400 (17)	−0.0101 (2)	0.21072 (13)	0.1034 (8)
O7	0.39882 (13)	0.1810 (2)	0.22575 (10)	0.0735 (6)
O8	0.55192 (10)	0.29224 (14)	0.60553 (9)	0.0517 (4)
O9	0.38360 (10)	−0.05263 (13)	0.54731 (9)	0.0501 (4)
O10	0.27374 (10)	0.36162 (14)	0.51066 (9)	0.0544 (5)
O11	0.18612 (14)	0.2261 (2)	0.61110 (12)	0.0802 (6)
O12	0.07827 (14)	0.3173 (2)	0.55353 (15)	0.1107 (9)
O13	−0.07427 (19)	0.0598 (3)	0.39067 (16)	0.1369 (13)
O14	−0.0034 (2)	−0.0854 (4)	0.34104 (18)	0.1460 (14)
O15	0.3059 (7)	0.8311 (10)	0.3338 (6)	0.112 (3)	0.25
H1A	0.5215 (16)	0.188 (2)	0.4194 (12)	0.047 (7)*
H2A	0.4307 (17)	0.519 (3)	0.4003 (13)	0.065 (8)*
H5A	0.5069 (16)	0.075 (2)	0.5918 (12)	0.048 (7)*
H6A	0.4201 (15)	0.403 (2)	0.5586 (11)	0.046 (7)*
H9A	0.242 (2)	0.507 (3)	0.4982 (16)	0.100 (10)*
H10	0.301 (2)	0.553 (3)	0.2815 (19)	0.101 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0379 (12)	0.0329 (11)	0.0502 (15)	0.0000 (10)	−0.0031 (11)	0.0029 (10)
C2	0.0346 (12)	0.0361 (11)	0.0472 (14)	0.0022 (10)	−0.0031 (10)	0.0048 (10)
C3	0.0345 (11)	0.0343 (11)	0.0425 (13)	0.0005 (9)	−0.0043 (10)	0.0018 (10)
C4	0.0378 (12)	0.0331 (11)	0.0405 (13)	−0.0002 (9)	0.0015 (10)	0.0010 (10)
C5	0.0413 (13)	0.0330 (11)	0.0482 (14)	−0.0021 (9)	−0.0025 (11)	0.0100 (10)
C6	0.0417 (14)	0.0448 (13)	0.0650 (17)	−0.0020 (11)	−0.0008 (12)	0.0049 (12)
C7	0.0403 (14)	0.0642 (17)	0.082 (2)	−0.0041 (12)	−0.0072 (14)	0.0227 (16)
C8	0.0547 (17)	0.0672 (18)	0.0574 (18)	−0.0231 (14)	−0.0187 (14)	0.0147 (15)
C9	0.0689 (19)	0.0590 (16)	0.0505 (17)	−0.0171 (14)	−0.0097 (14)	0.0023 (13)
C10	0.0492 (14)	0.0428 (13)	0.0478 (15)	−0.0063 (11)	−0.0054 (12)	0.0035 (11)
C11	0.0346 (12)	0.0325 (11)	0.0520 (15)	−0.0001 (9)	−0.0004 (11)	0.0023 (10)
C12	0.0351 (12)	0.0315 (11)	0.0473 (14)	0.0007 (9)	0.0004 (10)	0.0007 (10)
C13	0.0302 (11)	0.0312 (11)	0.0503 (14)	−0.0010 (9)	−0.0020 (10)	0.0023 (10)
C14	0.0323 (12)	0.0327 (11)	0.0509 (14)	0.0025 (9)	−0.0005 (10)	0.0037 (10)
C15	0.0361 (12)	0.0334 (11)	0.0557 (15)	−0.0035 (9)	−0.0049 (11)	0.0116 (11)
C16	0.0523 (15)	0.0396 (13)	0.0634 (17)	−0.0073 (11)	−0.0073 (13)	0.0049 (12)
C17	0.077 (2)	0.0494 (15)	0.0633 (19)	−0.0224 (14)	−0.0185 (15)	0.0129 (13)
C18	0.0473 (17)	0.076 (2)	0.075 (2)	−0.0262 (15)	−0.0223 (15)	0.0277 (17)
C19	0.0365 (14)	0.078 (2)	0.085 (2)	−0.0084 (13)	−0.0068 (14)	0.0288 (18)
C20	0.0357 (13)	0.0511 (14)	0.0710 (18)	−0.0039 (11)	−0.0030 (12)	0.0156 (13)
C21	0.073 (2)	0.0631 (19)	0.146 (3)	−0.0026 (16)	−0.014 (2)	0.024 (2)
C22	0.0570 (19)	0.099 (3)	0.121 (3)	0.0029 (17)	−0.0150 (19)	−0.006 (2)
C23	0.202 (5)	0.153 (4)	0.079 (3)	0.050 (4)	0.025 (3)	−0.009 (3)
N1	0.0356 (10)	0.0291 (10)	0.0535 (13)	0.0048 (8)	−0.0074 (9)	0.0019 (9)
N2	0.0393 (11)	0.0268 (10)	0.0666 (14)	0.0017 (8)	−0.0092 (10)	−0.0007 (9)
N3	0.0672 (15)	0.0638 (15)	0.0561 (15)	0.0007 (13)	0.0006 (12)	−0.0126 (12)
N4	0.072 (2)	0.116 (3)	0.078 (2)	−0.0380 (19)	−0.0195 (16)	0.0198 (19)
N5	0.0321 (10)	0.0303 (10)	0.0591 (13)	0.0031 (8)	−0.0073 (9)	0.0012 (9)
N6	0.0375 (10)	0.0248 (9)	0.0595 (13)	−0.0011 (8)	−0.0055 (9)	0.0018 (9)
N7	0.0423 (13)	0.0651 (15)	0.103 (2)	0.0020 (12)	0.0183 (14)	−0.0020 (15)
N8	0.073 (2)	0.120 (3)	0.098 (3)	−0.047 (2)	−0.0348 (19)	0.046 (2)
N9	0.0573 (13)	0.0423 (12)	0.0743 (17)	0.0121 (10)	−0.0035 (12)	0.0044 (11)
N10	0.093 (2)	0.0820 (19)	0.0712 (19)	−0.0091 (16)	0.0058 (16)	0.0140 (16)
C24	0.078 (5)	0.220 (12)	0.120 (6)	−0.044 (7)	0.019 (5)	0.010 (9)
C25	0.077 (7)	0.147 (9)	0.071 (5)	−0.001 (6)	−0.016 (5)	0.007 (6)
C26	0.163 (9)	0.097 (6)	0.240 (11)	0.042 (6)	0.033 (9)	0.079 (7)
C24'	0.070 (5)	0.145 (9)	0.085 (6)	−0.017 (6)	0.016 (4)	0.036 (7)
C25'	0.070 (8)	0.214 (17)	0.107 (8)	−0.013 (9)	−0.041 (6)	0.016 (12)
C26'	0.199 (12)	0.099 (7)	0.168 (9)	−0.004 (8)	−0.043 (10)	0.033 (7)
O1	0.0434 (9)	0.0375 (8)	0.0794 (13)	−0.0030 (7)	−0.0200 (9)	0.0010 (8)
O2	0.0409 (9)	0.0354 (8)	0.0724 (12)	0.0064 (7)	−0.0071 (8)	0.0059 (8)
O3	0.0463 (9)	0.0297 (8)	0.0637 (11)	0.0029 (7)	−0.0088 (8)	−0.0038 (7)
O4	0.113 (2)	0.138 (2)	0.093 (2)	−0.0637 (18)	−0.0212 (16)	−0.0162 (18)
O5	0.0599 (15)	0.183 (3)	0.142 (3)	−0.0275 (18)	−0.0307 (16)	0.010 (2)
O6	0.1144 (19)	0.0792 (16)	0.119 (2)	0.0062 (14)	0.0223 (16)	−0.0437 (15)
O7	0.0633 (12)	0.0905 (15)	0.0681 (14)	−0.0123 (11)	0.0136 (10)	−0.0077 (11)
O8	0.0375 (9)	0.0384 (8)	0.0757 (12)	−0.0049 (7)	−0.0147 (8)	0.0018 (8)
O9	0.0439 (9)	0.0267 (8)	0.0772 (12)	0.0019 (6)	−0.0098 (8)	−0.0011 (8)
O10	0.0398 (9)	0.0344 (8)	0.0866 (13)	0.0058 (7)	−0.0094 (8)	0.0104 (8)
O11	0.0713 (14)	0.0872 (15)	0.0830 (16)	−0.0027 (11)	0.0122 (12)	−0.0153 (13)
O12	0.0624 (13)	0.1029 (18)	0.169 (3)	0.0362 (13)	0.0214 (15)	−0.0064 (17)
O13	0.0581 (16)	0.193 (3)	0.151 (3)	−0.0261 (19)	−0.0423 (17)	0.038 (2)
O14	0.135 (3)	0.155 (3)	0.135 (3)	−0.078 (2)	−0.064 (2)	0.006 (2)
O15	0.096 (7)	0.117 (8)	0.120 (9)	0.001 (6)	−0.012 (6)	0.015 (7)

C1—O1	1.224 (2)	C22—N9	1.462 (4)
C1—N2	1.361 (3)	C22—H22A	0.9600
C1—N1	1.361 (3)	C22—H22B	0.9600
C2—O2	1.258 (2)	C22—H22C	0.9600
C2—N2	1.384 (3)	C23—N9	1.458 (5)
C2—C3	1.401 (3)	C23—H23A	0.9600
C3—C4	1.416 (3)	C23—H23B	0.9600
C3—C5	1.465 (3)	C23—H23C	0.9600
C4—O3	1.242 (2)	N1—H1A	0.80 (2)
C4—N1	1.394 (3)	N2—H2A	0.89 (3)
C5—C6	1.399 (3)	N3—O7	1.212 (3)
C5—C10	1.402 (3)	N3—O6	1.217 (3)
C6—C7	1.386 (3)	N4—O5	1.213 (4)
C6—H6	0.9300	N4—O4	1.225 (4)
C7—C8	1.372 (4)	N5—H5A	0.84 (2)
C7—H7	0.9300	N6—H6A	0.85 (2)
C8—C9	1.359 (4)	N7—O11	1.208 (3)
C8—N4	1.470 (4)	N7—O12	1.229 (3)
C9—C10	1.381 (3)	N8—O14	1.202 (5)
C9—H9	0.9300	N8—O13	1.239 (5)
C10—N3	1.465 (3)	N9—H9A	1.04 (3)
C11—O8	1.225 (2)	N10—C24	1.375 (8)
C11—N5	1.359 (3)	N10—C25'	1.390 (12)
C11—N6	1.360 (3)	N10—C26'	1.445 (9)
C12—O9	1.244 (2)	N10—C25	1.480 (10)
C12—N5	1.394 (3)	N10—C26	1.575 (8)
C12—C13	1.416 (3)	N10—C24'	1.593 (9)
C13—C14	1.406 (3)	N10—H10	1.02 (4)
C13—C15	1.456 (3)	C24—H24A	0.9600
C14—O10	1.246 (2)	C24—H24B	0.9600
C14—N6	1.382 (3)	C24—H24C	0.9600
C15—C16	1.392 (3)	C25—H25A	0.9600
C15—C20	1.402 (3)	C25—H25B	0.9600
C16—C17	1.384 (3)	C25—H25C	0.9600
C16—H16	0.9300	C26—H26A	0.9600
C17—C18	1.374 (4)	C26—H26B	0.9600
C17—H17	0.9300	C26—H26C	0.9600
C18—C19	1.356 (4)	C24'—H24D	0.9600
C18—N8	1.471 (4)	C24'—H24E	0.9600
C19—C20	1.374 (3)	C24'—H24F	0.9600
C19—H19	0.9300	C25'—H25D	0.9600
C20—N7	1.469 (4)	C25'—H25E	0.9600
C21—N9	1.459 (4)	C25'—H25F	0.9600
C21—H21A	0.9600	C26'—H26D	0.9600
C21—H21B	0.9600	C26'—H26E	0.9600
C21—H21C	0.9600	C26'—H26F	0.9600
O1—C1—N2	122.3 (2)	C2—N2—H2A	116.5 (16)
O1—C1—N1	123.1 (2)	O7—N3—O6	123.4 (3)
N2—C1—N1	114.60 (19)	O7—N3—C10	118.5 (2)
O2—C2—N2	116.01 (19)	O6—N3—C10	118.1 (2)
O2—C2—C3	126.6 (2)	O5—N4—O4	124.4 (3)
N2—C2—C3	117.34 (18)	O5—N4—C8	117.5 (4)
C2—C3—C4	119.78 (18)	O4—N4—C8	118.2 (3)
C2—C3—C5	119.30 (18)	C11—N5—C12	126.03 (19)
C4—C3—C5	120.92 (18)	C11—N5—H5A	115.3 (16)
O3—C4—N1	117.40 (18)	C12—N5—H5A	118.6 (16)
O3—C4—C3	125.84 (19)	C11—N6—C14	125.57 (18)
N1—C4—C3	116.76 (18)	C11—N6—H6A	118.0 (15)
C6—C5—C10	115.5 (2)	C14—N6—H6A	116.5 (15)
C6—C5—C3	120.9 (2)	O11—N7—O12	123.5 (3)
C10—C5—C3	123.5 (2)	O11—N7—C20	119.0 (2)
C7—C6—C5	122.1 (3)	O12—N7—C20	117.5 (3)
C7—C6—H6	119.0	O14—N8—O13	125.1 (3)
C5—C6—H6	119.0	O14—N8—C18	117.9 (4)
C8—C7—C6	119.0 (3)	O13—N8—C18	116.9 (4)
C8—C7—H7	120.5	C23—N9—C21	112.8 (3)
C6—C7—H7	120.5	C23—N9—C22	112.8 (3)
C9—C8—C7	121.6 (2)	C21—N9—C22	110.7 (3)
C9—C8—N4	118.4 (3)	C23—N9—H9A	103.1 (18)
C7—C8—N4	120.0 (3)	C21—N9—H9A	110.7 (18)
C8—C9—C10	118.7 (3)	C22—N9—H9A	106.3 (18)
C8—C9—H9	120.6	C24—N10—C25'	126.3 (12)
C10—C9—H9	120.6	C24—N10—C26'	59.3 (6)
C9—C10—C5	122.8 (2)	C25'—N10—C26'	118.1 (8)
C9—C10—N3	115.1 (2)	C24—N10—C25	119.6 (8)
C5—C10—N3	121.7 (2)	C25'—N10—C25	26.4 (8)
O8—C11—N5	123.06 (19)	C26'—N10—C25	141.1 (8)
O8—C11—N6	122.11 (19)	C24—N10—C26	109.4 (7)
N5—C11—N6	114.83 (19)	C25'—N10—C26	79.7 (8)
O9—C12—N5	117.75 (18)	C26'—N10—C26	51.6 (6)
O9—C12—C13	126.16 (19)	C25—N10—C26	105.6 (6)
N5—C12—C13	116.05 (18)	C24—N10—C24'	43.4 (6)
C14—C13—C12	120.20 (18)	C25'—N10—C24'	109.9 (9)
C14—C13—C15	118.26 (18)	C26'—N10—C24'	102.6 (7)
C12—C13—C15	121.46 (18)	C25—N10—C24'	88.7 (7)
O10—C14—N6	118.06 (18)	C26—N10—C24'	152.1 (5)
O10—C14—C13	124.63 (19)	C24—N10—H10	116.9 (19)
N6—C14—C13	117.29 (18)	C25'—N10—H10	112 (2)
C16—C15—C20	115.5 (2)	C26'—N10—H10	114 (2)
C16—C15—C13	120.5 (2)	C25—N10—H10	101 (2)
C20—C15—C13	123.8 (2)	C26—N10—H10	102.1 (19)
C17—C16—C15	122.4 (3)	C24'—N10—H10	98.3 (19)
C17—C16—H16	118.8	N10—C24—H24A	109.5
C15—C16—H16	118.8	N10—C24—H24B	109.5
C18—C17—C16	118.6 (3)	H24A—C24—H24B	109.5
C18—C17—H17	120.7	N10—C24—H24C	109.5
C16—C17—H17	120.7	H24A—C24—H24C	109.5
C19—C18—C17	121.8 (2)	H24B—C24—H24C	109.5
C19—C18—N8	118.6 (3)	N10—C25—H25A	109.5
C17—C18—N8	119.6 (4)	N10—C25—H25B	109.5
C18—C19—C20	118.6 (3)	H25A—C25—H25B	109.5
C18—C19—H19	120.7	N10—C25—H25C	109.5
C20—C19—H19	120.7	H25A—C25—H25C	109.5
C19—C20—C15	123.0 (3)	H25B—C25—H25C	109.5
C19—C20—N7	115.0 (2)	N10—C26—H26A	109.5
C15—C20—N7	121.9 (2)	N10—C26—H26B	109.5
N9—C21—H21A	109.5	H26A—C26—H26B	109.5
N9—C21—H21B	109.5	N10—C26—H26C	109.5
H21A—C21—H21B	109.5	H26A—C26—H26C	109.5
N9—C21—H21C	109.5	H26B—C26—H26C	109.5
H21A—C21—H21C	109.5	N10—C24'—H24D	109.5
H21B—C21—H21C	109.5	N10—C24'—H24E	109.5
N9—C22—H22A	109.5	H24D—C24'—H24E	109.5
N9—C22—H22B	109.5	N10—C24'—H24F	109.5
H22A—C22—H22B	109.5	H24D—C24'—H24F	109.5
N9—C22—H22C	109.5	H24E—C24'—H24F	109.5
H22A—C22—H22C	109.5	N10—C25'—H25D	109.5
H22B—C22—H22C	109.5	N10—C25'—H25E	109.5
N9—C23—H23A	109.5	H25D—C25'—H25E	109.5
N9—C23—H23B	109.5	N10—C25'—H25F	109.5
H23A—C23—H23B	109.5	H25D—C25'—H25F	109.5
N9—C23—H23C	109.5	H25E—C25'—H25F	109.5
H23A—C23—H23C	109.5	N10—C26'—H26D	109.5
H23B—C23—H23C	109.5	N10—C26'—H26E	109.5
C1—N1—C4	125.44 (19)	H26D—C26'—H26E	109.5
C1—N1—H1A	117.2 (17)	N10—C26'—H26F	109.5
C4—N1—H1A	117.3 (17)	H26D—C26'—H26F	109.5
C1—N2—C2	125.73 (19)	H26E—C26'—H26F	109.5
C1—N2—H2A	117.0 (17)
O2—C2—C3—C4	−179.0 (2)	C16—C17—C18—N8	177.1 (2)
N2—C2—C3—C4	4.4 (3)	C17—C18—C19—C20	0.1 (4)
O2—C2—C3—C5	1.0 (4)	N8—C18—C19—C20	−178.7 (2)
N2—C2—C3—C5	−175.6 (2)	C18—C19—C20—C15	2.8 (4)
C2—C3—C4—O3	177.7 (2)	C18—C19—C20—N7	−174.2 (2)
C5—C3—C4—O3	−2.3 (4)	C16—C15—C20—C19	−3.7 (4)
C2—C3—C4—N1	−2.0 (3)	C13—C15—C20—C19	170.6 (2)
C5—C3—C4—N1	178.0 (2)	C16—C15—C20—N7	173.1 (2)
C2—C3—C5—C6	−43.2 (3)	C13—C15—C20—N7	−12.6 (4)
C4—C3—C5—C6	136.7 (2)	O1—C1—N1—C4	−174.0 (2)
C2—C3—C5—C10	137.7 (2)	N2—C1—N1—C4	6.4 (3)
C4—C3—C5—C10	−42.4 (3)	O3—C4—N1—C1	176.6 (2)
C10—C5—C6—C7	1.0 (3)	C3—C4—N1—C1	−3.7 (3)
C3—C5—C6—C7	−178.1 (2)	O1—C1—N2—C2	176.8 (2)
C5—C6—C7—C8	3.5 (4)	N1—C1—N2—C2	−3.6 (3)
C6—C7—C8—C9	−4.4 (4)	O2—C2—N2—C1	−178.5 (2)
C6—C7—C8—N4	177.6 (2)	C3—C2—N2—C1	−1.6 (4)
C7—C8—C9—C10	0.7 (4)	C9—C10—N3—O7	136.7 (2)
N4—C8—C9—C10	178.7 (2)	C5—C10—N3—O7	−36.0 (3)
C8—C9—C10—C5	4.2 (4)	C9—C10—N3—O6	−40.0 (3)
C8—C9—C10—N3	−168.4 (2)	C5—C10—N3—O6	147.4 (3)
C6—C5—C10—C9	−4.9 (3)	C9—C8—N4—O5	−171.8 (3)
C3—C5—C10—C9	174.2 (2)	C7—C8—N4—O5	6.2 (4)
C6—C5—C10—N3	167.2 (2)	C9—C8—N4—O4	8.3 (4)
C3—C5—C10—N3	−13.7 (3)	C7—C8—N4—O4	−173.7 (3)
O9—C12—C13—C14	179.0 (2)	O8—C11—N5—C12	−179.1 (2)
N5—C12—C13—C14	1.3 (3)	N6—C11—N5—C12	0.6 (3)
O9—C12—C13—C15	−4.2 (4)	O9—C12—N5—C11	−179.6 (2)
N5—C12—C13—C15	178.1 (2)	C13—C12—N5—C11	−1.7 (3)
C12—C13—C14—O10	178.4 (2)	O8—C11—N6—C14	−179.3 (2)
C15—C13—C14—O10	1.5 (4)	N5—C11—N6—C14	1.0 (3)
C12—C13—C14—N6	0.0 (3)	O10—C14—N6—C11	−179.8 (2)
C15—C13—C14—N6	−176.9 (2)	C13—C14—N6—C11	−1.3 (3)
C14—C13—C15—C16	130.0 (2)	C19—C20—N7—O11	144.5 (3)
C12—C13—C15—C16	−46.9 (3)	C15—C20—N7—O11	−32.6 (4)
C14—C13—C15—C20	−44.1 (3)	C19—C20—N7—O12	−33.2 (3)
C12—C13—C15—C20	139.1 (2)	C15—C20—N7—O12	149.8 (2)
C20—C15—C16—C17	1.9 (3)	C19—C18—N8—O14	−175.6 (3)
C13—C15—C16—C17	−172.6 (2)	C17—C18—N8—O14	5.6 (4)
C15—C16—C17—C18	0.6 (4)	C19—C18—N8—O13	4.6 (4)
C16—C17—C18—C19	−1.7 (4)	C17—C18—N8—O13	−174.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O9i	0.80 (2)	2.09 (2)	2.888 (2)	175 (2)
N2—H2A···O8ii	0.89 (3)	2.02 (3)	2.905 (2)	173 (2)
N5—H5A···O3i	0.84 (2)	2.10 (2)	2.931 (2)	169 (2)
N6—H6A···O1ii	0.85 (2)	2.04 (3)	2.889 (2)	177 (2)
N9—H9A···O10	1.04 (3)	1.62 (4)	2.650 (2)	167 (3)
N10—H10···O2	1.02 (4)	1.63 (4)	2.644 (3)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O9i	0.80 (2)	2.09 (2)	2.888 (2)	175 (2)
N2—H2A⋯O8ii	0.89 (3)	2.02 (3)	2.905 (2)	173 (2)
N5—H5A⋯O3i	0.84 (2)	2.10 (2)	2.931 (2)	169 (2)
N6—H6A⋯O1ii	0.85 (2)	2.04 (3)	2.889 (2)	177 (2)
N9—H9A⋯O10	1.04 (3)	1.62 (4)	2.650 (2)	167 (3)
N10—H10⋯O2	1.02 (4)	1.63 (4)	2.644 (3)	173 (3)

Symmetry codes: (i) ; (ii) .