N,N-Diethyl-2-hy-droxy-ethanaminium 5-(5-chloro-2,4-dinitro-phen-yl)-2,6-dioxo-1,2,3,6-tetra-hydro-pyrimidin-4-olate hemihydrate.

The asymmetric unit of the title salt, C(6)H(16)NO(+)·C(10)H(4)ClN(4)O(7) (-)·0.5H(2)O, contains two cations, two anions and one water mol-ecule. In one independent anion, one nitro group is rotationally disordered over two orientations in a 0.657 (8):0.343 (8) ratio. In the crystal, inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link all the components into ribbons extending along [100].

Related literature

For details of the pharmacological properties of pyrimidine derivatives, see: Hueso et al. (2003 ▶); Colorado & Brodbelt (1996 ▶); Kalaivani et al. (2008 ▶); Kalaivani & Buvaneswari (2010 ▶). For the crystal structures of related compounds, see: Kalaivani & Malarvizhi (2009 ▶); Buvaneswari & Kalaivani (2011 ▶).

Experimental

Crystal data

C6H16NO+·C10H4ClN4O7 −·0.5H2O

M = 454.83

Triclinic,

a = 12.3775 (7) Å

b = 12.8109 (8) Å

c = 13.5834 (9) Å

α = 101.497 (4)°

β = 99.142 (3)°

γ = 99.718 (3)°

V = 2038.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 294 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.901, T max = 0.942

36654 measured reflections

7179 independent reflections

5639 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.138

S = 1.07

7179 reflections

598 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.72 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003248/cv5228sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003248/cv5228Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003248/cv5228Isup3.cml

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

C6H16NO+·C10H4ClN4O7−·0.5H2O	Z = 4
Mr = 454.83	F(000) = 948
Triclinic, P1	Dx = 1.482 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.3775 (7) Å	Cell parameters from 6078 reflections
b = 12.8109 (8) Å	θ = 2.5–27.0°
c = 13.5834 (9) Å	µ = 0.25 mm−1
α = 101.497 (4)°	T = 294 K
β = 99.142 (3)°	Block, red
γ = 99.718 (3)°	0.30 × 0.25 × 0.20 mm
V = 2038.6 (2) Å3

Bruker Kappa APEXII CCD diffractometer	7179 independent reflections
Radiation source: fine-focus sealed tube	5639 reflections with I > 2σ(I)
graphite	Rint = 0.031
ω and φ scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
Tmin = 0.901, Tmax = 0.942	k = −15→15
36654 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0773P)2 + 0.6949P] where P = (Fo2 + 2Fc2)/3
7179 reflections	(Δ/σ)max < 0.001
598 parameters	Δρmax = 0.72 e Å−3
4 restraints	Δρmin = −0.32 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	Occ. (<1)
C1	0.73604 (16)	0.44594 (17)	−0.05043 (16)	0.0343 (5)
C2	0.60151 (16)	0.40344 (17)	0.05684 (15)	0.0309 (4)
C3	0.65908 (16)	0.32478 (16)	0.08526 (15)	0.0307 (4)
C4	0.75520 (16)	0.30658 (16)	0.04682 (16)	0.0330 (4)
C5	0.62072 (15)	0.26499 (16)	0.15797 (15)	0.0309 (4)
C6	0.59379 (16)	0.32162 (17)	0.24693 (16)	0.0331 (4)
H6	0.6024	0.3968	0.2582	0.040*
C7	0.55516 (17)	0.27072 (18)	0.31856 (16)	0.0369 (5)
C8	0.54654 (19)	0.15898 (19)	0.30541 (17)	0.0407 (5)
C9	0.57638 (18)	0.10095 (19)	0.22112 (18)	0.0423 (5)
H9	0.5736	0.0267	0.2131	0.051*
C10	0.61032 (17)	0.15297 (17)	0.14886 (16)	0.0356 (5)
C11	0.3083 (2)	0.2680 (2)	0.1612 (2)	0.0532 (6)
H11A	0.3635	0.3322	0.1995	0.064*
H11B	0.3476	0.2110	0.1388	0.064*
C12	0.23267 (19)	0.23115 (19)	0.23035 (18)	0.0448 (5)
H12A	0.2757	0.2063	0.2839	0.054*
H12B	0.2042	0.2925	0.2629	0.054*
C13	0.1698 (2)	0.0418 (2)	0.1186 (2)	0.0518 (6)
H13A	0.1032	−0.0071	0.0756	0.062*
H13B	0.2191	0.0628	0.0739	0.062*
C14	0.2266 (3)	−0.0185 (3)	0.1866 (3)	0.0890 (11)
H14A	0.2944	0.0280	0.2278	0.133*
H14B	0.2441	−0.0813	0.1456	0.133*
H14C	0.1781	−0.0414	0.2303	0.133*
C15	0.0554 (2)	0.1188 (2)	0.2403 (2)	0.0544 (6)
H15A	0.0367	0.1866	0.2717	0.065*
H15B	0.0904	0.0894	0.2947	0.065*
C16	−0.0505 (3)	0.0396 (3)	0.1822 (3)	0.0785 (9)
H16A	−0.0810	0.0644	0.1236	0.118*
H16B	−0.1039	0.0350	0.2261	0.118*
H16C	−0.0341	−0.0309	0.1600	0.118*
N1	0.78912 (15)	0.37048 (15)	−0.01912 (14)	0.0371 (4)
N2	0.64328 (14)	0.45918 (15)	−0.01195 (14)	0.0347 (4)
N3	0.62568 (17)	0.08057 (16)	0.05553 (17)	0.0474 (5)
N4	0.5033 (2)	0.0960 (2)	0.37474 (18)	0.0619 (6)
N5	0.13683 (15)	0.14164 (15)	0.17278 (14)	0.0383 (4)
H5	0.1002	0.1682	0.1228	0.046*
O1	0.77048 (13)	0.49917 (13)	−0.10940 (13)	0.0454 (4)
O2	0.81174 (12)	0.24002 (13)	0.06849 (13)	0.0452 (4)
O3	0.51542 (12)	0.42531 (13)	0.08530 (12)	0.0404 (4)
O4	0.58787 (16)	0.09712 (15)	−0.02727 (14)	0.0595 (5)
O5	0.67161 (17)	0.00520 (15)	0.06664 (17)	0.0685 (6)
O6	0.5307 (3)	0.0114 (2)	0.3777 (2)	0.1097 (10)
O7	0.4287 (2)	0.12591 (19)	0.41688 (18)	0.0825 (7)
O8	0.24764 (14)	0.29216 (14)	0.07518 (13)	0.0521 (4)
H8	0.2158	0.3415	0.0939	0.078*
O9	1.00189 (14)	0.19327 (14)	0.01618 (15)	0.0494 (4)
Cl1	0.52193 (6)	0.35212 (5)	0.42199 (5)	0.05531 (19)
H9A	0.9462 (17)	0.210 (2)	0.040 (2)	0.069 (9)*
H9B	1.030 (2)	0.241 (2)	−0.013 (3)	0.100 (13)*
H2	0.604 (2)	0.501 (2)	−0.0340 (18)	0.042 (7)*
H1	0.847 (2)	0.3646 (18)	−0.0432 (17)	0.034 (6)*
C17	1.03464 (17)	0.41704 (18)	−0.14752 (16)	0.0368 (5)
C18	1.16333 (15)	0.44983 (15)	−0.26248 (15)	0.0288 (4)
C19	1.10360 (16)	0.52326 (16)	−0.29751 (15)	0.0305 (4)
C20	1.01060 (16)	0.54779 (17)	−0.25484 (15)	0.0324 (4)
C21	1.13552 (15)	0.57684 (16)	−0.37742 (15)	0.0298 (4)
C22	1.13816 (17)	0.68886 (17)	−0.36557 (17)	0.0349 (5)
H22	1.1219	0.7271	−0.3059	0.042*
C23	1.16361 (19)	0.74390 (17)	−0.43818 (18)	0.0413 (5)
C24	1.19176 (19)	0.68958 (19)	−0.52631 (18)	0.0438 (5)
C25	1.19514 (18)	0.58186 (18)	−0.54005 (17)	0.0394 (5)
H25	1.2168	0.5457	−0.5978	0.047*
C26	1.16608 (16)	0.52740 (16)	−0.46732 (15)	0.0313 (4)
C27	1.3675 (3)	0.2472 (3)	−0.1336 (2)	0.0674 (8)
H27A	1.4013	0.2112	−0.0839	0.081*
H27B	1.4104	0.3210	−0.1199	0.081*
C28	1.3701 (3)	0.1885 (3)	−0.2380 (2)	0.0689 (8)
H28A	1.3201	0.1178	−0.2534	0.083*
H28B	1.4451	0.1762	−0.2395	0.083*
C29	1.4321 (2)	0.2946 (2)	−0.3634 (2)	0.0583 (7)
H29A	1.4687	0.2376	−0.3916	0.070*
H29B	1.4018	0.3248	−0.4192	0.070*
C30	1.5159 (3)	0.3808 (3)	−0.2878 (3)	0.0836 (10)
H30A	1.4789	0.4318	−0.2518	0.125*
H30B	1.5664	0.4178	−0.3226	0.125*
H30C	1.5571	0.3489	−0.2399	0.125*
C31	1.2477 (3)	0.1671 (2)	−0.4101 (2)	0.0680 (8)
H31A	1.2399	0.2005	−0.4682	0.082*
H31B	1.2727	0.0997	−0.4309	0.082*
C32	1.1376 (3)	0.1425 (3)	−0.3805 (3)	0.0822 (10)
H32A	1.1450	0.1089	−0.3233	0.123*
H32B	1.0849	0.0938	−0.4374	0.123*
H32C	1.1117	0.2088	−0.3618	0.123*
N6	0.98182 (15)	0.49133 (16)	−0.18171 (15)	0.0394 (4)
N7	1.12560 (14)	0.40106 (15)	−0.18818 (14)	0.0353 (4)
N8	1.16366 (16)	0.40985 (15)	−0.49451 (13)	0.0381 (4)
N9	1.2163 (3)	0.7445 (2)	−0.6078 (2)	0.0779 (8)
N10	1.33782 (18)	0.24545 (16)	−0.31949 (16)	0.0493 (5)
H10	1.3060	0.3004	−0.2917	0.059*
O10	1.00397 (14)	0.36887 (15)	−0.08398 (13)	0.0519 (4)
O11	0.95065 (12)	0.61060 (13)	−0.27829 (12)	0.0418 (4)
O12	1.24892 (11)	0.42489 (11)	−0.29138 (11)	0.0335 (3)
O13	1.08502 (14)	0.34754 (13)	−0.48101 (13)	0.0483 (4)
O14	1.24008 (15)	0.38142 (14)	−0.53307 (13)	0.0555 (5)
O15	1.1439 (4)	0.7960 (5)	−0.6401 (4)	0.118 (2)	0.670 (9)
O16	1.2847 (6)	0.7283 (7)	−0.6494 (7)	0.142 (5)	0.670 (9)
O15'	1.3101 (9)	0.8218 (9)	−0.5731 (7)	0.125 (5)	0.330 (9)
O16'	1.2011 (14)	0.7054 (10)	−0.6879 (7)	0.133 (8)	0.330 (9)
O17	1.25677 (16)	0.24953 (16)	−0.12333 (14)	0.0623 (5)
H17	1.2564	0.2834	−0.0655	0.094*
Cl2	1.16163 (7)	0.88047 (5)	−0.41687 (6)	0.0707 (2)
H7	1.161 (2)	0.355 (2)	−0.1702 (19)	0.043 (7)*
H6A	0.928 (2)	0.5042 (19)	−0.1581 (18)	0.036 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0309 (10)	0.0399 (12)	0.0377 (11)	0.0116 (9)	0.0126 (9)	0.0136 (9)
C2	0.0273 (10)	0.0387 (11)	0.0304 (10)	0.0113 (8)	0.0090 (8)	0.0106 (9)
C3	0.0272 (10)	0.0351 (11)	0.0329 (11)	0.0087 (8)	0.0094 (8)	0.0104 (9)
C4	0.0283 (10)	0.0350 (11)	0.0401 (11)	0.0101 (9)	0.0107 (9)	0.0130 (9)
C5	0.0221 (9)	0.0381 (11)	0.0357 (11)	0.0096 (8)	0.0062 (8)	0.0128 (9)
C6	0.0286 (10)	0.0380 (11)	0.0356 (11)	0.0109 (8)	0.0074 (9)	0.0109 (9)
C7	0.0328 (10)	0.0487 (13)	0.0322 (11)	0.0118 (9)	0.0088 (9)	0.0116 (9)
C8	0.0422 (12)	0.0496 (13)	0.0372 (12)	0.0119 (10)	0.0125 (10)	0.0206 (10)
C9	0.0433 (12)	0.0390 (12)	0.0518 (14)	0.0142 (10)	0.0144 (11)	0.0182 (10)
C10	0.0322 (10)	0.0397 (12)	0.0382 (12)	0.0115 (9)	0.0117 (9)	0.0098 (9)
C11	0.0386 (12)	0.0547 (15)	0.0649 (17)	0.0085 (11)	0.0021 (12)	0.0181 (13)
C12	0.0474 (13)	0.0452 (13)	0.0415 (13)	0.0132 (10)	0.0049 (10)	0.0094 (10)
C13	0.0555 (14)	0.0512 (14)	0.0495 (14)	0.0158 (12)	0.0194 (12)	0.0027 (11)
C14	0.101 (3)	0.070 (2)	0.103 (3)	0.051 (2)	0.014 (2)	0.0113 (19)
C15	0.0640 (16)	0.0570 (15)	0.0549 (15)	0.0191 (13)	0.0339 (13)	0.0196 (12)
C16	0.0639 (18)	0.088 (2)	0.088 (2)	−0.0028 (16)	0.0363 (17)	0.0307 (19)
N1	0.0301 (9)	0.0450 (11)	0.0484 (11)	0.0180 (8)	0.0207 (8)	0.0201 (9)
N2	0.0307 (9)	0.0432 (10)	0.0410 (10)	0.0189 (8)	0.0147 (8)	0.0196 (8)
N3	0.0462 (11)	0.0405 (11)	0.0575 (14)	0.0067 (9)	0.0253 (10)	0.0060 (10)
N4	0.0846 (17)	0.0630 (15)	0.0533 (13)	0.0228 (13)	0.0316 (12)	0.0280 (11)
N5	0.0423 (10)	0.0432 (10)	0.0362 (10)	0.0150 (8)	0.0146 (8)	0.0148 (8)
O1	0.0426 (8)	0.0569 (10)	0.0557 (10)	0.0232 (7)	0.0266 (8)	0.0332 (8)
O2	0.0372 (8)	0.0490 (9)	0.0673 (11)	0.0240 (7)	0.0249 (8)	0.0309 (8)
O3	0.0340 (8)	0.0566 (10)	0.0459 (9)	0.0254 (7)	0.0198 (7)	0.0246 (7)
O4	0.0692 (12)	0.0605 (12)	0.0431 (10)	0.0026 (9)	0.0183 (9)	0.0026 (9)
O5	0.0776 (13)	0.0476 (11)	0.0946 (15)	0.0287 (10)	0.0454 (12)	0.0139 (10)
O6	0.166 (3)	0.0938 (18)	0.129 (2)	0.0676 (19)	0.090 (2)	0.0805 (18)
O7	0.1039 (17)	0.0817 (15)	0.0758 (14)	0.0151 (13)	0.0538 (13)	0.0256 (12)
O8	0.0519 (10)	0.0570 (10)	0.0532 (10)	0.0116 (8)	0.0154 (8)	0.0223 (8)
O9	0.0389 (9)	0.0554 (10)	0.0675 (12)	0.0219 (8)	0.0200 (8)	0.0280 (9)
Cl1	0.0693 (4)	0.0612 (4)	0.0400 (3)	0.0161 (3)	0.0252 (3)	0.0086 (3)
C17	0.0343 (11)	0.0450 (12)	0.0384 (12)	0.0144 (9)	0.0127 (9)	0.0169 (10)
C18	0.0287 (10)	0.0291 (10)	0.0292 (10)	0.0074 (8)	0.0068 (8)	0.0059 (8)
C19	0.0308 (10)	0.0320 (10)	0.0326 (10)	0.0107 (8)	0.0094 (8)	0.0103 (8)
C20	0.0315 (10)	0.0349 (11)	0.0338 (11)	0.0121 (9)	0.0078 (9)	0.0096 (9)
C21	0.0237 (9)	0.0319 (10)	0.0345 (11)	0.0083 (8)	0.0041 (8)	0.0082 (8)
C22	0.0342 (11)	0.0327 (11)	0.0408 (12)	0.0101 (9)	0.0106 (9)	0.0101 (9)
C23	0.0428 (12)	0.0297 (11)	0.0535 (14)	0.0083 (9)	0.0098 (10)	0.0140 (10)
C24	0.0460 (13)	0.0455 (13)	0.0468 (13)	0.0073 (10)	0.0150 (11)	0.0241 (11)
C25	0.0381 (11)	0.0443 (13)	0.0388 (12)	0.0096 (10)	0.0124 (10)	0.0117 (10)
C26	0.0300 (10)	0.0309 (10)	0.0345 (11)	0.0084 (8)	0.0067 (8)	0.0096 (9)
C27	0.0680 (18)	0.088 (2)	0.0527 (16)	0.0331 (16)	0.0112 (14)	0.0186 (15)
C28	0.086 (2)	0.0715 (19)	0.0711 (19)	0.0483 (17)	0.0276 (16)	0.0301 (16)
C29	0.0615 (16)	0.0704 (18)	0.0538 (16)	0.0268 (14)	0.0279 (13)	0.0156 (13)
C30	0.0648 (19)	0.096 (3)	0.080 (2)	0.0135 (18)	0.0264 (17)	−0.0080 (19)
C31	0.094 (2)	0.0429 (15)	0.0690 (19)	0.0187 (15)	0.0204 (17)	0.0095 (13)
C32	0.081 (2)	0.0540 (18)	0.103 (3)	0.0091 (16)	0.002 (2)	0.0162 (18)
N6	0.0351 (10)	0.0512 (12)	0.0476 (11)	0.0238 (9)	0.0221 (9)	0.0245 (9)
N7	0.0353 (9)	0.0413 (10)	0.0408 (10)	0.0191 (8)	0.0156 (8)	0.0204 (8)
N8	0.0470 (11)	0.0368 (10)	0.0306 (9)	0.0148 (9)	0.0029 (8)	0.0070 (8)
N9	0.118 (2)	0.0601 (16)	0.078 (2)	0.0223 (17)	0.0525 (19)	0.0383 (16)
N10	0.0656 (13)	0.0449 (11)	0.0542 (12)	0.0313 (10)	0.0286 (10)	0.0203 (10)
O10	0.0513 (9)	0.0700 (11)	0.0608 (11)	0.0309 (9)	0.0327 (8)	0.0438 (9)
O11	0.0402 (8)	0.0490 (9)	0.0500 (9)	0.0259 (7)	0.0164 (7)	0.0231 (7)
O12	0.0322 (7)	0.0352 (8)	0.0412 (8)	0.0154 (6)	0.0153 (6)	0.0138 (6)
O13	0.0550 (10)	0.0349 (8)	0.0498 (10)	0.0011 (7)	0.0026 (8)	0.0108 (7)
O14	0.0700 (11)	0.0579 (11)	0.0498 (10)	0.0366 (9)	0.0221 (9)	0.0103 (8)
O15	0.149 (4)	0.155 (5)	0.118 (4)	0.090 (3)	0.066 (3)	0.110 (4)
O16	0.160 (6)	0.184 (9)	0.188 (9)	0.113 (7)	0.139 (7)	0.141 (8)
O15'	0.154 (9)	0.103 (7)	0.093 (6)	−0.068 (6)	0.040 (6)	0.032 (6)
O16'	0.221 (16)	0.107 (9)	0.039 (5)	−0.058 (11)	0.027 (7)	0.020 (4)
O17	0.0757 (13)	0.0789 (13)	0.0519 (11)	0.0432 (11)	0.0218 (9)	0.0299 (10)
Cl2	0.0971 (6)	0.0333 (3)	0.0919 (6)	0.0188 (3)	0.0292 (4)	0.0254 (3)

C1—O1	1.231 (2)	C17—O10	1.228 (2)
C1—N1	1.355 (3)	C17—N6	1.356 (3)
C1—N2	1.357 (3)	C17—N7	1.358 (3)
C2—O3	1.246 (2)	C18—O12	1.255 (2)
C2—N2	1.395 (3)	C18—N7	1.389 (3)
C2—C3	1.408 (3)	C18—C19	1.400 (3)
C3—C4	1.409 (3)	C19—C20	1.422 (3)
C3—C5	1.454 (3)	C19—C21	1.465 (3)
C4—O2	1.241 (2)	C20—O11	1.236 (2)
C4—N1	1.394 (3)	C20—N6	1.396 (3)
C5—C10	1.398 (3)	C21—C26	1.398 (3)
C5—C6	1.399 (3)	C21—C22	1.406 (3)
C6—C7	1.377 (3)	C22—C23	1.368 (3)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.390 (3)	C23—C24	1.386 (3)
C7—Cl1	1.725 (2)	C23—Cl2	1.721 (2)
C8—C9	1.374 (3)	C24—C25	1.364 (3)
C8—N4	1.464 (3)	C24—N9	1.468 (3)
C9—C10	1.372 (3)	C25—C26	1.377 (3)
C9—H9	0.9300	C25—H25	0.9300
C10—N3	1.473 (3)	C26—N8	1.471 (3)
C11—O8	1.403 (3)	C27—O17	1.404 (3)
C11—C12	1.512 (3)	C27—C28	1.476 (4)
C11—H11A	0.9700	C27—H27A	0.9700
C11—H11B	0.9700	C27—H27B	0.9700
C12—N5	1.491 (3)	C28—N10	1.482 (3)
C12—H12A	0.9700	C28—H28A	0.9700
C12—H12B	0.9700	C28—H28B	0.9700
C13—C14	1.486 (4)	C29—C30	1.474 (4)
C13—N5	1.497 (3)	C29—N10	1.495 (3)
C13—H13A	0.9700	C29—H29A	0.9700
C13—H13B	0.9700	C29—H29B	0.9700
C14—H14A	0.9600	C30—H30A	0.9600
C14—H14B	0.9600	C30—H30B	0.9600
C14—H14C	0.9600	C30—H30C	0.9600
C15—N5	1.498 (3)	C31—C32	1.482 (5)
C15—C16	1.508 (4)	C31—N10	1.568 (4)
C15—H15A	0.9700	C31—H31A	0.9700
C15—H15B	0.9700	C31—H31B	0.9700
C16—H16A	0.9600	C32—H32A	0.9600
C16—H16B	0.9600	C32—H32B	0.9600
C16—H16C	0.9600	C32—H32C	0.9600
N1—H1	0.84 (2)	N6—H6A	0.81 (2)
N2—H2	0.85 (3)	N7—H7	0.84 (3)
N3—O4	1.221 (3)	N8—O13	1.213 (2)
N3—O5	1.223 (3)	N8—O14	1.225 (2)
N4—O6	1.194 (3)	N9—O16'	1.076 (9)
N4—O7	1.235 (3)	N9—O16	1.115 (5)
N5—H5	0.9100	N9—O15	1.275 (5)
O8—H8	0.8200	N9—O15'	1.343 (8)
O9—H9A	0.844 (10)	N10—H10	0.9100
O9—H9B	0.847 (10)	O17—H17	0.8200
O1—C1—N1	121.94 (18)	O12—C18—N7	116.88 (17)
O1—C1—N2	122.51 (19)	O12—C18—C19	125.81 (18)
N1—C1—N2	115.54 (18)	N7—C18—C19	117.30 (17)
O3—C2—N2	117.45 (17)	C18—C19—C20	120.00 (18)
O3—C2—C3	125.94 (18)	C18—C19—C21	121.25 (17)
N2—C2—C3	116.58 (16)	C20—C19—C21	118.75 (17)
C2—C3—C4	120.63 (18)	O11—C20—N6	116.96 (17)
C2—C3—C5	119.26 (17)	O11—C20—C19	126.90 (19)
C4—C3—C5	120.07 (17)	N6—C20—C19	116.09 (17)
O2—C4—N1	118.45 (17)	C26—C21—C22	114.50 (18)
O2—C4—C3	125.05 (19)	C26—C21—C19	126.22 (17)
N1—C4—C3	116.49 (17)	C22—C21—C19	119.28 (17)
C10—C5—C6	115.15 (18)	C23—C22—C21	122.7 (2)
C10—C5—C3	125.52 (18)	C23—C22—H22	118.6
C6—C5—C3	119.31 (18)	C21—C22—H22	118.6
C7—C6—C5	122.8 (2)	C22—C23—C24	119.8 (2)
C7—C6—H6	118.6	C22—C23—Cl2	118.85 (18)
C5—C6—H6	118.6	C24—C23—Cl2	121.37 (17)
C6—C7—C8	119.43 (19)	C25—C24—C23	120.1 (2)
C6—C7—Cl1	116.87 (17)	C25—C24—N9	118.2 (2)
C8—C7—Cl1	123.70 (16)	C23—C24—N9	121.7 (2)
C9—C8—C7	119.59 (19)	C24—C25—C26	119.1 (2)
C9—C8—N4	116.3 (2)	C24—C25—H25	120.5
C7—C8—N4	124.1 (2)	C26—C25—H25	120.5
C10—C9—C8	119.8 (2)	C25—C26—C21	123.73 (19)
C10—C9—H9	120.1	C25—C26—N8	114.20 (18)
C8—C9—H9	120.1	C21—C26—N8	121.99 (17)
C9—C10—C5	123.18 (19)	O17—C27—C28	110.3 (3)
C9—C10—N3	114.93 (19)	O17—C27—H27A	109.6
C5—C10—N3	121.68 (18)	C28—C27—H27A	109.6
O8—C11—C12	111.63 (19)	O17—C27—H27B	109.6
O8—C11—H11A	109.3	C28—C27—H27B	109.6
C12—C11—H11A	109.3	H27A—C27—H27B	108.1
O8—C11—H11B	109.3	C27—C28—N10	114.6 (2)
C12—C11—H11B	109.3	C27—C28—H28A	108.6
H11A—C11—H11B	108.0	N10—C28—H28A	108.6
N5—C12—C11	111.96 (19)	C27—C28—H28B	108.6
N5—C12—H12A	109.2	N10—C28—H28B	108.6
C11—C12—H12A	109.2	H28A—C28—H28B	107.6
N5—C12—H12B	109.2	C30—C29—N10	113.5 (2)
C11—C12—H12B	109.2	C30—C29—H29A	108.9
H12A—C12—H12B	107.9	N10—C29—H29A	108.9
C14—C13—N5	115.1 (2)	C30—C29—H29B	108.9
C14—C13—H13A	108.5	N10—C29—H29B	108.9
N5—C13—H13A	108.5	H29A—C29—H29B	107.7
C14—C13—H13B	108.5	C29—C30—H30A	109.5
N5—C13—H13B	108.5	C29—C30—H30B	109.5
H13A—C13—H13B	107.5	H30A—C30—H30B	109.5
C13—C14—H14A	109.5	C29—C30—H30C	109.5
C13—C14—H14B	109.5	H30A—C30—H30C	109.5
H14A—C14—H14B	109.5	H30B—C30—H30C	109.5
C13—C14—H14C	109.5	C32—C31—N10	111.7 (2)
H14A—C14—H14C	109.5	C32—C31—H31A	109.3
H14B—C14—H14C	109.5	N10—C31—H31A	109.3
N5—C15—C16	112.4 (2)	C32—C31—H31B	109.3
N5—C15—H15A	109.1	N10—C31—H31B	109.3
C16—C15—H15A	109.1	H31A—C31—H31B	107.9
N5—C15—H15B	109.1	C31—C32—H32A	109.5
C16—C15—H15B	109.1	C31—C32—H32B	109.5
H15A—C15—H15B	107.9	H32A—C32—H32B	109.5
C15—C16—H16A	109.5	C31—C32—H32C	109.5
C15—C16—H16B	109.5	H32A—C32—H32C	109.5
H16A—C16—H16B	109.5	H32B—C32—H32C	109.5
C15—C16—H16C	109.5	C17—N6—C20	126.19 (18)
H16A—C16—H16C	109.5	C17—N6—H6A	117.4 (17)
H16B—C16—H16C	109.5	C20—N6—H6A	116.4 (17)
C1—N1—C4	125.43 (17)	C17—N7—C18	125.73 (18)
C1—N1—H1	113.6 (15)	C17—N7—H7	118.2 (17)
C4—N1—H1	120.9 (15)	C18—N7—H7	115.9 (17)
C1—N2—C2	125.29 (18)	O13—N8—O14	124.30 (19)
C1—N2—H2	118.9 (16)	O13—N8—C26	118.52 (17)
C2—N2—H2	115.6 (16)	O14—N8—C26	117.12 (18)
O4—N3—O5	124.6 (2)	O16'—N9—O16	57.1 (8)
O4—N3—C10	118.05 (19)	O16'—N9—O15	81.8 (10)
O5—N3—C10	117.3 (2)	O16—N9—O15	121.3 (4)
O6—N4—O7	122.9 (2)	O16'—N9—O15'	115.5 (8)
O6—N4—C8	118.8 (2)	O16—N9—O15'	67.1 (7)
O7—N4—C8	117.6 (2)	O15—N9—O15'	103.5 (7)
C12—N5—C13	114.51 (18)	O16'—N9—C24	125.0 (6)
C12—N5—C15	110.22 (18)	O16—N9—C24	121.6 (4)
C13—N5—C15	113.58 (18)	O15—N9—C24	116.0 (3)
C12—N5—H5	105.9	O15'—N9—C24	110.0 (4)
C13—N5—H5	105.9	C28—N10—C29	115.2 (2)
C15—N5—H5	105.9	C28—N10—C31	110.8 (2)
C11—O8—H8	109.5	C29—N10—C31	108.0 (2)
H9A—O9—H9B	111.6 (17)	C28—N10—H10	107.5
O10—C17—N6	122.98 (19)	C29—N10—H10	107.5
O10—C17—N7	122.42 (19)	C31—N10—H10	107.5
N6—C17—N7	114.59 (18)	C27—O17—H17	109.5
O3—C2—C3—C4	179.2 (2)	O12—C18—C19—C21	2.3 (3)
N2—C2—C3—C4	1.3 (3)	N7—C18—C19—C21	−178.60 (18)
O3—C2—C3—C5	−3.0 (3)	C18—C19—C20—O11	−180.0 (2)
N2—C2—C3—C5	179.08 (18)	C21—C19—C20—O11	0.5 (3)
C2—C3—C4—O2	179.2 (2)	C18—C19—C20—N6	−2.7 (3)
C5—C3—C4—O2	1.5 (3)	C21—C19—C20—N6	177.79 (18)
C2—C3—C4—N1	0.4 (3)	C18—C19—C21—C26	43.5 (3)
C5—C3—C4—N1	−177.35 (18)	C20—C19—C21—C26	−137.0 (2)
C2—C3—C5—C10	136.1 (2)	C18—C19—C21—C22	−135.7 (2)
C4—C3—C5—C10	−46.2 (3)	C20—C19—C21—C22	43.7 (3)
C2—C3—C5—C6	−45.7 (3)	C26—C21—C22—C23	2.8 (3)
C4—C3—C5—C6	132.0 (2)	C19—C21—C22—C23	−177.86 (19)
C10—C5—C6—C7	−2.7 (3)	C21—C22—C23—C24	−2.1 (3)
C3—C5—C6—C7	178.89 (18)	C21—C22—C23—Cl2	178.70 (16)
C5—C6—C7—C8	2.8 (3)	C22—C23—C24—C25	−0.6 (3)
C5—C6—C7—Cl1	−178.12 (15)	Cl2—C23—C24—C25	178.48 (18)
C6—C7—C8—C9	−0.2 (3)	C22—C23—C24—N9	178.1 (3)
Cl1—C7—C8—C9	−179.13 (17)	Cl2—C23—C24—N9	−2.8 (3)
C6—C7—C8—N4	−178.0 (2)	C23—C24—C25—C26	2.5 (3)
Cl1—C7—C8—N4	3.1 (3)	N9—C24—C25—C26	−176.3 (2)
C7—C8—C9—C10	−2.5 (3)	C24—C25—C26—C21	−1.7 (3)
N4—C8—C9—C10	175.5 (2)	C24—C25—C26—N8	175.07 (19)
C8—C9—C10—C5	2.6 (3)	C22—C21—C26—C25	−0.9 (3)
C8—C9—C10—N3	−172.2 (2)	C19—C21—C26—C25	179.86 (19)
C6—C5—C10—C9	0.0 (3)	C22—C21—C26—N8	−177.43 (17)
C3—C5—C10—C9	178.3 (2)	C19—C21—C26—N8	3.3 (3)
C6—C5—C10—N3	174.38 (18)	O17—C27—C28—N10	68.8 (4)
C3—C5—C10—N3	−7.3 (3)	O10—C17—N6—C20	−178.8 (2)
O8—C11—C12—N5	51.5 (3)	N7—C17—N6—C20	2.0 (3)
O1—C1—N1—C4	−179.6 (2)	O11—C20—N6—C17	178.2 (2)
N2—C1—N1—C4	0.8 (3)	C19—C20—N6—C17	0.7 (3)
O2—C4—N1—C1	179.5 (2)	O10—C17—N7—C18	177.9 (2)
C3—C4—N1—C1	−1.6 (3)	N6—C17—N7—C18	−3.0 (3)
O1—C1—N2—C2	−178.4 (2)	O12—C18—N7—C17	−179.7 (2)
N1—C1—N2—C2	1.2 (3)	C19—C18—N7—C17	1.1 (3)
O3—C2—N2—C1	179.7 (2)	C25—C26—N8—O13	−134.9 (2)
C3—C2—N2—C1	−2.2 (3)	C21—C26—N8—O13	42.0 (3)
C9—C10—N3—O4	135.0 (2)	C25—C26—N8—O14	42.5 (2)
C5—C10—N3—O4	−39.9 (3)	C21—C26—N8—O14	−140.6 (2)
C9—C10—N3—O5	−42.1 (3)	C25—C24—N9—O16'	29.0 (14)
C5—C10—N3—O5	143.1 (2)	C23—C24—N9—O16'	−149.7 (13)
C9—C8—N4—O6	25.7 (4)	C25—C24—N9—O16	−40.6 (8)
C7—C8—N4—O6	−156.4 (3)	C23—C24—N9—O16	140.7 (8)
C9—C8—N4—O7	−144.8 (3)	C25—C24—N9—O15	127.6 (4)
C7—C8—N4—O7	33.1 (4)	C23—C24—N9—O15	−51.2 (5)
C11—C12—N5—C13	58.8 (3)	C25—C24—N9—O15'	−115.3 (8)
C11—C12—N5—C15	−171.7 (2)	C23—C24—N9—O15'	65.9 (8)
C14—C13—N5—C12	66.5 (3)	C27—C28—N10—C29	106.6 (3)
C14—C13—N5—C15	−61.3 (3)	C27—C28—N10—C31	−130.3 (3)
C16—C15—N5—C12	172.3 (2)	C30—C29—N10—C28	−62.9 (3)
C16—C15—N5—C13	−57.7 (3)	C30—C29—N10—C31	172.6 (3)
O12—C18—C19—C20	−177.21 (19)	C32—C31—N10—C28	71.2 (3)
N7—C18—C19—C20	1.9 (3)	C32—C31—N10—C29	−161.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O9i	0.91	1.85	2.749 (2)	167.
O8—H8···O1ii	0.82	1.98	2.674 (2)	141.
O9—H9A···O2	0.84 (1)	1.85 (1)	2.691 (2)	171 (3)
O9—H9B···O10	0.85 (1)	2.11 (2)	2.850 (2)	146 (3)
N2—H2···O3ii	0.85 (3)	1.99 (3)	2.826 (2)	168 (2)
N1—H1···O10	0.84 (2)	2.10 (2)	2.933 (2)	171 (2)
N10—H10···O12	0.91	1.85	2.698 (2)	154.
O17—H17···O8iii	0.82	1.91	2.667 (2)	153.
N7—H7···O17	0.84 (3)	2.07 (3)	2.911 (2)	176 (2)
N6—H6A···O1	0.81 (2)	2.16 (2)	2.947 (2)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯O9i	0.91	1.85	2.749 (2)	167
O8—H8⋯O1ii	0.82	1.98	2.674 (2)	141
O9—H9A⋯O2	0.84 (1)	1.85 (1)	2.691 (2)	171 (3)
O9—H9B⋯O10	0.85 (1)	2.11 (2)	2.850 (2)	146 (3)
N2—H2⋯O3ii	0.85 (3)	1.99 (3)	2.826 (2)	168 (2)
N1—H1⋯O10	0.84 (2)	2.10 (2)	2.933 (2)	171 (2)
N10—H10⋯O12	0.91	1.85	2.698 (2)	154
O17—H17⋯O8iii	0.82	1.91	2.667 (2)	153
N7—H7⋯O17	0.84 (3)	2.07 (3)	2.911 (2)	176 (2)
N6—H6A⋯O1	0.81 (2)	2.16 (2)	2.947 (2)	167 (2)

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