5-Benzoyl-4-hydr-oxy-6-(4-nitro-phen-yl)-4-trifluoro-meth-yl-3,4,5,6-tetrahydro-pyrimidin-2(1H)-one monohydrate.

The asymmetric unit of the title compound, C(18)H(14)F(3)N(3)O(5)·H(2)O, contains two independent formula units. The two heterocyclic mol-ecules differ in the orientations of the benzoyl-phenyl group with respect to the tetra-hydro-pyrimidine ring [C-C-C-C torsion angles of 64.5 (3) and 67.1 (3)°]. In both mol-ecules the pyrimidine ring adopts a half-chair conformation. The mol-ecules are linked into a two-dimensional network parallel to (001) by N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the bioactivity of dihydro­pyrimidines, see: Brier et al. (2004 ▶); Cochran et al. (2005 ▶); Moran et al. (2007 ▶); Zorkun et al. (2006 ▶). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003 ▶); Ulrich (2004 ▶).

Experimental

Crystal data

C18H14F3N3O5·H2O

M = 427.34

Orthorhombic,

a = 14.389 (3) Å

b = 9.0391 (18) Å

c = 28.141 (6) Å

V = 3660.1 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.14 mm−1

T = 113 (2) K

0.32 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2002 ▶) T min = 0.958, T max = 0.973

28524 measured reflections

4437 independent reflections

4222 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.107

S = 1.06

4437 reflections

575 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680804124X/ci2728sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804124X/ci2728Isup2.hkl

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

C18H14F3N3O5·H2O	F(000) = 1760
Mr = 427.34	Dx = 1.551 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6634 reflections
a = 14.389 (3) Å	θ = 2.6–25.0°
b = 9.0391 (18) Å	µ = 0.14 mm−1
c = 28.141 (6) Å	T = 113 K
V = 3660.1 (13) Å3	Prism, colourless
Z = 8	0.32 × 0.22 × 0.20 mm

Rigaku Saturn diffractometer	4437 independent reflections
Radiation source: rotating anode	4222 reflections with I > 2σ(I)
confocal	Rint = 0.059
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.4°
ω scans	h = −18→18
Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2002)	k = −11→10
Tmin = 0.958, Tmax = 0.973	l = −36→37
28524 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0683P)2 + 0.2165P] where P = (Fo2 + 2Fc2)/3
4437 reflections	(Δ/σ)max = 0.044
575 parameters	Δρmax = 0.25 e Å−3
2 restraints	Δρmin = −0.31 e Å−3

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
N1	−0.09671 (16)	0.3614 (2)	0.59693 (8)	0.0172 (4)
H1	−0.158 (2)	0.351 (3)	0.5850 (13)	0.022 (8)*
N2	0.05590 (16)	0.2777 (3)	0.59022 (9)	0.0212 (5)
H2A	0.088 (3)	0.198 (4)	0.5786 (14)	0.032 (10)*
N3	0.40154 (18)	0.2937 (3)	0.73426 (9)	0.0275 (5)
N4	0.17052 (16)	1.1349 (2)	0.98405 (8)	0.0163 (4)
H4	0.117 (2)	1.137 (3)	0.9964 (13)	0.021 (8)*
N5	0.32327 (15)	1.2159 (3)	0.99252 (9)	0.0205 (5)
H5	0.364 (3)	1.277 (4)	1.0061 (14)	0.033 (9)*
N6	0.66618 (17)	1.2226 (3)	0.84793 (9)	0.0246 (5)
O1	−0.06318 (13)	0.1373 (2)	0.56457 (7)	0.0213 (4)
O2	0.09085 (15)	0.7349 (2)	0.62345 (8)	0.0281 (5)
O3	0.38832 (18)	0.2127 (3)	0.76856 (9)	0.0419 (6)
O4	0.47761 (17)	0.3480 (3)	0.72524 (11)	0.0509 (7)
O5	−0.04878 (14)	0.5953 (2)	0.56735 (7)	0.0196 (4)
H5A	−0.101 (3)	0.613 (4)	0.5511 (14)	0.029*
O6	0.20406 (14)	1.35887 (19)	1.01700 (7)	0.0207 (4)
O7	0.36076 (15)	0.7632 (2)	0.95958 (8)	0.0262 (4)
O8	0.64950 (18)	1.2982 (3)	0.81335 (9)	0.0431 (6)
O9	0.74415 (16)	1.1810 (3)	0.85877 (10)	0.0427 (6)
O10	0.21816 (13)	0.9012 (2)	1.01373 (7)	0.0205 (4)
H10A	0.1681 (18)	0.889 (4)	1.0294 (13)	0.031*
C1	−0.03449 (18)	0.2551 (3)	0.58280 (10)	0.0172 (5)
C2	0.09768 (18)	0.4139 (3)	0.60829 (9)	0.0175 (5)
H2	0.1185	0.4770	0.5811	0.021*
C3	0.02400 (17)	0.4968 (3)	0.63747 (9)	0.0164 (5)
H3	0.0100	0.4373	0.6666	0.020*
C4	−0.06557 (18)	0.5103 (3)	0.60803 (9)	0.0155 (5)
C5	0.17991 (18)	0.3796 (3)	0.64030 (9)	0.0180 (5)
C6	0.17091 (19)	0.2707 (3)	0.67560 (11)	0.0227 (6)
H6	0.1153	0.2144	0.6777	0.027*
C7	0.2428 (2)	0.2452 (3)	0.70731 (10)	0.0229 (6)
H7	0.2368	0.1733	0.7317	0.027*
C8	0.32376 (19)	0.3271 (3)	0.70250 (10)	0.0200 (5)
C9	0.33499 (19)	0.4337 (3)	0.66753 (10)	0.0224 (6)
H9	0.3915	0.4873	0.6648	0.027*
C10	0.26174 (19)	0.4602 (3)	0.63676 (10)	0.0207 (5)
H10	0.2676	0.5342	0.6130	0.025*
C11	0.06423 (19)	0.6473 (3)	0.65320 (10)	0.0191 (5)
C12	0.0703 (2)	0.6817 (3)	0.70501 (11)	0.0228 (6)
C13	0.0605 (2)	0.5753 (3)	0.74055 (11)	0.0296 (6)
H13	0.0485	0.4751	0.7324	0.036*
C14	0.0685 (3)	0.6161 (4)	0.78780 (13)	0.0411 (8)
H14	0.0626	0.5434	0.8120	0.049*
C15	0.0846 (3)	0.7598 (5)	0.79987 (15)	0.0499 (10)
H15	0.0898	0.7863	0.8324	0.060*
C16	0.0935 (3)	0.8662 (4)	0.76563 (17)	0.0517 (11)
H16	0.1037	0.9663	0.7745	0.062*
C17	0.0875 (3)	0.8281 (4)	0.71771 (14)	0.0361 (8)
H17	0.0950	0.9016	0.6939	0.043*
C18	−0.14246 (19)	0.5841 (3)	0.63835 (10)	0.0194 (5)
C19	0.23177 (18)	1.2409 (3)	0.99904 (10)	0.0169 (5)
C20	0.36507 (18)	1.0817 (3)	0.97328 (10)	0.0189 (5)
H20	0.3873	1.0176	0.9999	0.023*
C21	0.29152 (17)	0.9978 (3)	0.94407 (9)	0.0161 (5)
H21	0.2781	1.0563	0.9147	0.019*
C22	0.20117 (18)	0.9860 (3)	0.97330 (9)	0.0174 (5)
C23	0.44638 (18)	1.1209 (3)	0.94105 (10)	0.0177 (5)
C24	0.43558 (19)	1.2302 (3)	0.90652 (11)	0.0230 (6)
H24	0.3790	1.2840	0.9047	0.028*
C25	0.5063 (2)	1.2605 (3)	0.87512 (11)	0.0231 (6)
H25	0.4986	1.3324	0.8508	0.028*
C26	0.58888 (18)	1.1836 (3)	0.87981 (10)	0.0194 (5)
C27	0.60266 (19)	1.0753 (3)	0.91366 (10)	0.0206 (5)
H27	0.6603	1.0247	0.9161	0.025*
C28	0.52921 (19)	1.0424 (3)	0.94424 (10)	0.0199 (5)
H28	0.5358	0.9663	0.9673	0.024*
C29	0.33101 (19)	0.8468 (3)	0.92912 (10)	0.0200 (5)
C30	0.3331 (2)	0.8049 (3)	0.87787 (11)	0.0238 (6)
C31	0.3250 (2)	0.9069 (3)	0.84102 (11)	0.0274 (6)
H31	0.3171	1.0090	0.8480	0.033*
C32	0.3284 (3)	0.8593 (4)	0.79407 (12)	0.0364 (8)
H32	0.3237	0.9292	0.7690	0.044*
C33	0.3385 (3)	0.7107 (4)	0.78375 (14)	0.0444 (9)
H33	0.3397	0.6785	0.7516	0.053*
C34	0.3470 (3)	0.6092 (4)	0.82007 (14)	0.0429 (9)
H34	0.3544	0.5072	0.8128	0.052*
C35	0.3447 (3)	0.6548 (3)	0.86693 (12)	0.0329 (7)
H35	0.3509	0.5843	0.8918	0.040*
C36	0.1248 (2)	0.9125 (3)	0.94281 (10)	0.0210 (5)
F1	−0.14776 (12)	0.52363 (19)	0.68178 (6)	0.0286 (4)
F2	−0.22576 (11)	0.57373 (19)	0.61866 (6)	0.0274 (4)
F3	−0.12376 (13)	0.72802 (19)	0.64456 (7)	0.0324 (4)
F4	0.04104 (12)	0.92471 (19)	0.96255 (6)	0.0280 (4)
F5	0.12020 (12)	0.97358 (19)	0.89937 (6)	0.0278 (4)
F6	0.14278 (13)	0.76842 (18)	0.93679 (8)	0.0322 (4)
O11	0.21603 (13)	0.1296 (2)	0.54929 (8)	0.0212 (4)
H11A	0.215 (3)	0.183 (4)	0.5257 (15)	0.032*
H11B	0.228 (3)	0.046 (4)	0.5390 (14)	0.032*
O12	0.01675 (13)	0.8681 (2)	0.53237 (8)	0.0213 (4)
H12A	0.012 (2)	0.807 (4)	0.5554 (15)	0.032*
H12B	0.015 (3)	0.948 (4)	0.5459 (14)	0.032*

	U11	U22	U33	U12	U13	U23
N1	0.0173 (11)	0.0159 (10)	0.0185 (10)	−0.0003 (8)	−0.0023 (9)	−0.0037 (8)
N2	0.0182 (11)	0.0221 (12)	0.0233 (12)	0.0018 (9)	−0.0025 (9)	−0.0082 (9)
N3	0.0243 (12)	0.0319 (13)	0.0263 (13)	0.0078 (10)	−0.0046 (10)	−0.0066 (11)
N4	0.0139 (11)	0.0149 (10)	0.0200 (11)	0.0003 (8)	0.0022 (9)	−0.0035 (8)
N5	0.0146 (10)	0.0204 (11)	0.0265 (13)	−0.0035 (8)	0.0029 (9)	−0.0085 (10)
N6	0.0225 (12)	0.0256 (11)	0.0257 (13)	−0.0043 (9)	0.0055 (10)	−0.0005 (10)
O1	0.0200 (9)	0.0186 (9)	0.0254 (10)	0.0006 (7)	−0.0051 (8)	−0.0064 (7)
O2	0.0314 (11)	0.0223 (9)	0.0306 (12)	−0.0066 (8)	−0.0053 (9)	0.0047 (8)
O3	0.0397 (14)	0.0552 (15)	0.0309 (13)	0.0083 (11)	−0.0100 (10)	0.0120 (12)
O4	0.0212 (12)	0.0774 (19)	0.0542 (17)	−0.0049 (12)	−0.0122 (11)	0.0189 (15)
O5	0.0198 (10)	0.0227 (9)	0.0162 (9)	−0.0035 (7)	−0.0041 (7)	0.0070 (7)
O6	0.0205 (10)	0.0172 (9)	0.0246 (10)	−0.0014 (7)	0.0049 (8)	−0.0074 (7)
O7	0.0313 (11)	0.0257 (10)	0.0217 (11)	0.0099 (9)	0.0031 (8)	0.0039 (8)
O8	0.0383 (14)	0.0547 (15)	0.0363 (14)	0.0066 (11)	0.0154 (11)	0.0214 (13)
O9	0.0190 (11)	0.0639 (16)	0.0453 (14)	0.0005 (11)	0.0045 (10)	0.0152 (12)
O10	0.0176 (10)	0.0233 (9)	0.0206 (9)	0.0010 (7)	0.0033 (7)	0.0070 (8)
C1	0.0186 (12)	0.0169 (12)	0.0161 (13)	0.0005 (10)	−0.0019 (10)	−0.0006 (9)
C2	0.0157 (12)	0.0177 (11)	0.0191 (12)	−0.0010 (9)	0.0000 (9)	−0.0006 (9)
C3	0.0161 (12)	0.0171 (11)	0.0159 (11)	−0.0010 (9)	−0.0020 (9)	−0.0005 (9)
C4	0.0163 (12)	0.0152 (11)	0.0150 (11)	0.0005 (9)	−0.0020 (9)	0.0003 (9)
C5	0.0179 (13)	0.0175 (12)	0.0187 (12)	0.0005 (9)	−0.0014 (10)	−0.0027 (9)
C6	0.0165 (12)	0.0248 (13)	0.0267 (15)	−0.0027 (10)	−0.0009 (11)	0.0028 (11)
C7	0.0249 (14)	0.0238 (13)	0.0200 (15)	0.0072 (11)	0.0004 (11)	0.0026 (10)
C8	0.0166 (13)	0.0243 (12)	0.0192 (12)	0.0052 (10)	−0.0033 (10)	−0.0051 (10)
C9	0.0163 (12)	0.0233 (13)	0.0277 (15)	−0.0012 (10)	−0.0008 (11)	−0.0038 (11)
C10	0.0206 (13)	0.0204 (12)	0.0210 (13)	−0.0002 (10)	−0.0011 (10)	0.0003 (10)
C11	0.0172 (12)	0.0166 (12)	0.0234 (13)	−0.0005 (9)	−0.0063 (10)	−0.0005 (10)
C12	0.0225 (13)	0.0210 (13)	0.0249 (14)	0.0008 (10)	−0.0059 (11)	−0.0067 (11)
C13	0.0373 (17)	0.0302 (15)	0.0214 (14)	0.0032 (12)	−0.0072 (12)	−0.0052 (12)
C14	0.050 (2)	0.050 (2)	0.0231 (16)	0.0086 (17)	−0.0084 (15)	−0.0097 (15)
C15	0.059 (3)	0.064 (2)	0.0273 (19)	0.001 (2)	−0.0115 (17)	−0.0219 (18)
C16	0.057 (2)	0.042 (2)	0.056 (3)	−0.0058 (17)	−0.011 (2)	−0.032 (2)
C17	0.0393 (19)	0.0251 (15)	0.044 (2)	−0.0038 (13)	−0.0058 (15)	−0.0093 (14)
C18	0.0193 (13)	0.0186 (12)	0.0202 (13)	−0.0016 (10)	−0.0013 (10)	−0.0007 (10)
C19	0.0183 (12)	0.0168 (12)	0.0156 (12)	−0.0015 (10)	0.0018 (10)	−0.0011 (9)
C20	0.0171 (12)	0.0204 (12)	0.0193 (12)	0.0002 (9)	0.0039 (10)	−0.0011 (10)
C21	0.0159 (12)	0.0148 (11)	0.0174 (12)	−0.0002 (9)	0.0012 (9)	0.0012 (9)
C22	0.0192 (12)	0.0151 (11)	0.0178 (12)	−0.0001 (9)	0.0020 (9)	0.0005 (9)
C23	0.0154 (13)	0.0187 (12)	0.0191 (12)	−0.0017 (9)	0.0004 (10)	−0.0034 (10)
C24	0.0160 (12)	0.0257 (13)	0.0272 (15)	0.0000 (10)	−0.0012 (11)	0.0025 (11)
C25	0.0219 (13)	0.0239 (13)	0.0234 (15)	0.0018 (11)	−0.0005 (11)	0.0047 (11)
C26	0.0170 (13)	0.0221 (12)	0.0193 (12)	−0.0040 (9)	0.0022 (10)	−0.0016 (10)
C27	0.0193 (13)	0.0193 (12)	0.0231 (14)	0.0012 (10)	0.0014 (10)	−0.0004 (10)
C28	0.0199 (13)	0.0202 (12)	0.0196 (12)	0.0012 (10)	−0.0013 (10)	−0.0012 (10)
C29	0.0169 (13)	0.0201 (13)	0.0231 (14)	−0.0009 (10)	0.0038 (10)	−0.0012 (10)
C30	0.0224 (14)	0.0258 (14)	0.0233 (14)	0.0005 (11)	0.0076 (11)	−0.0031 (11)
C31	0.0305 (16)	0.0267 (14)	0.0249 (15)	0.0002 (12)	0.0049 (12)	−0.0012 (12)
C32	0.0425 (19)	0.0447 (19)	0.0221 (16)	0.0049 (15)	0.0058 (14)	−0.0001 (14)
C33	0.055 (2)	0.053 (2)	0.0260 (18)	0.0000 (17)	0.0102 (16)	−0.0170 (16)
C34	0.063 (3)	0.0310 (16)	0.0350 (18)	0.0015 (16)	0.0148 (17)	−0.0141 (14)
C35	0.0451 (19)	0.0243 (14)	0.0294 (17)	0.0044 (13)	0.0100 (14)	−0.0068 (12)
C36	0.0214 (14)	0.0177 (12)	0.0238 (13)	−0.0017 (10)	0.0015 (11)	−0.0021 (10)
F1	0.0313 (9)	0.0361 (9)	0.0182 (8)	0.0027 (7)	0.0060 (7)	0.0003 (7)
F2	0.0177 (8)	0.0352 (9)	0.0293 (9)	0.0046 (7)	−0.0009 (7)	−0.0078 (7)
F3	0.0316 (10)	0.0180 (8)	0.0475 (13)	0.0040 (7)	0.0041 (8)	−0.0103 (8)
F4	0.0183 (8)	0.0348 (9)	0.0310 (9)	−0.0038 (7)	0.0037 (7)	−0.0104 (8)
F5	0.0300 (9)	0.0331 (9)	0.0202 (8)	−0.0026 (7)	−0.0041 (7)	−0.0016 (7)
F6	0.0328 (10)	0.0178 (8)	0.0459 (12)	−0.0009 (7)	−0.0003 (8)	−0.0105 (8)
O11	0.0228 (10)	0.0166 (9)	0.0242 (10)	0.0021 (8)	−0.0009 (8)	0.0028 (8)
O12	0.0242 (11)	0.0171 (9)	0.0224 (10)	0.0020 (7)	0.0009 (8)	0.0011 (8)

N1—C1	1.372 (3)	C13—H13	0.95
N1—C4	1.452 (3)	C14—C15	1.362 (6)
N1—H1	0.95 (3)	C14—H14	0.95
N2—C1	1.333 (3)	C15—C16	1.367 (7)
N2—C2	1.461 (3)	C15—H15	0.95
N2—H2A	0.92 (4)	C16—C17	1.395 (6)
N3—O4	1.226 (4)	C16—H16	0.95
N3—O3	1.226 (4)	C17—H17	0.95
N3—C8	1.464 (3)	C18—F2	1.324 (3)
N4—C19	1.368 (3)	C18—F3	1.340 (3)
N4—C22	1.449 (3)	C18—F1	1.341 (3)
N4—H4	0.85 (4)	C20—C23	1.522 (4)
N5—C19	1.348 (3)	C20—C21	1.540 (4)
N5—C20	1.458 (3)	C20—H20	1.00
N5—H5	0.89 (4)	C21—C29	1.537 (4)
N6—O8	1.213 (4)	C21—C22	1.542 (3)
N6—O9	1.222 (3)	C21—H21	1.00
N6—C26	1.472 (3)	C22—C36	1.545 (4)
O1—C1	1.252 (3)	C23—C28	1.390 (4)
O2—C11	1.214 (4)	C23—C24	1.394 (4)
O5—C4	1.400 (3)	C24—C25	1.375 (4)
O5—H5A	0.89 (4)	C24—H24	0.95
O6—C19	1.246 (3)	C25—C26	1.383 (4)
O7—C29	1.221 (3)	C25—H25	0.95
O10—C22	1.393 (3)	C26—C27	1.380 (4)
O10—H10A	0.852 (19)	C27—C28	1.395 (4)
C2—C5	1.519 (4)	C27—H27	0.95
C2—C3	1.536 (4)	C28—H28	0.95
C2—H2	1.00	C29—C30	1.491 (4)
C3—C4	1.537 (3)	C30—C31	1.393 (4)
C3—C11	1.544 (4)	C30—C35	1.401 (4)
C3—H3	1.00	C31—C32	1.390 (4)
C4—C18	1.548 (4)	C31—H31	0.95
C5—C10	1.388 (4)	C32—C33	1.382 (5)
C5—C6	1.405 (4)	C32—H32	0.95
C6—C7	1.385 (4)	C33—C34	1.379 (6)
C6—H6	0.95	C33—H33	0.95
C7—C8	1.387 (4)	C34—C35	1.382 (5)
C7—H7	0.95	C34—H34	0.95
C8—C9	1.387 (4)	C35—H35	0.95
C9—C10	1.385 (4)	C36—F4	1.331 (3)
C9—H9	0.95	C36—F6	1.338 (3)
C10—H10	0.95	C36—F5	1.343 (3)
C11—C12	1.493 (4)	O11—H11A	0.82 (4)
C12—C17	1.393 (4)	O11—H11B	0.83 (4)
C12—C13	1.395 (4)	O12—H12A	0.85 (4)
C13—C14	1.385 (4)	O12—H12B	0.82 (4)
C1—N1—C4	120.7 (2)	C12—C17—C16	119.6 (4)
C1—N1—H1	116 (2)	C12—C17—H17	120.2
C4—N1—H1	116.9 (19)	C16—C17—H17	120.2
C1—N2—C2	125.8 (2)	F2—C18—F3	107.8 (2)
C1—N2—H2A	108 (2)	F2—C18—F1	107.5 (2)
C2—N2—H2A	125 (2)	F3—C18—F1	106.8 (2)
O4—N3—O3	122.7 (3)	F2—C18—C4	112.7 (2)
O4—N3—C8	118.3 (3)	F3—C18—C4	110.3 (2)
O3—N3—C8	119.0 (3)	F1—C18—C4	111.5 (2)
C19—N4—C22	121.3 (2)	O6—C19—N5	120.7 (2)
C19—N4—H4	117 (2)	O6—C19—N4	121.2 (2)
C22—N4—H4	112 (2)	N5—C19—N4	118.0 (2)
C19—N5—C20	126.3 (2)	N5—C20—C23	110.1 (2)
C19—N5—H5	118 (3)	N5—C20—C21	108.9 (2)
C20—N5—H5	114 (3)	C23—C20—C21	109.0 (2)
O8—N6—O9	123.7 (3)	N5—C20—H20	109.6
O8—N6—C26	118.3 (3)	C23—C20—H20	109.6
O9—N6—C26	117.9 (3)	C21—C20—H20	109.6
C4—O5—H5A	112 (2)	C29—C21—C20	109.2 (2)
C22—O10—H10A	110 (3)	C29—C21—C22	113.3 (2)
O1—C1—N2	121.1 (2)	C20—C21—C22	109.2 (2)
O1—C1—N1	119.9 (2)	C29—C21—H21	108.3
N2—C1—N1	118.9 (2)	C20—C21—H21	108.3
N2—C2—C5	110.8 (2)	C22—C21—H21	108.3
N2—C2—C3	108.2 (2)	O10—C22—N4	113.2 (2)
C5—C2—C3	108.7 (2)	O10—C22—C21	109.0 (2)
N2—C2—H2	109.7	N4—C22—C21	107.7 (2)
C5—C2—H2	109.7	O10—C22—C36	110.0 (2)
C3—C2—H2	109.7	N4—C22—C36	107.4 (2)
C2—C3—C4	109.2 (2)	C21—C22—C36	109.5 (2)
C2—C3—C11	108.9 (2)	C28—C23—C24	120.1 (2)
C4—C3—C11	113.5 (2)	C28—C23—C20	120.1 (2)
C2—C3—H3	108.3	C24—C23—C20	119.6 (2)
C4—C3—H3	108.3	C25—C24—C23	120.4 (3)
C11—C3—H3	108.3	C25—C24—H24	119.8
O5—C4—N1	112.7 (2)	C23—C24—H24	119.8
O5—C4—C3	109.8 (2)	C24—C25—C26	118.3 (3)
N1—C4—C3	107.5 (2)	C24—C25—H25	120.8
O5—C4—C18	109.7 (2)	C26—C25—H25	120.8
N1—C4—C18	107.3 (2)	C27—C26—C25	123.1 (3)
C3—C4—C18	109.7 (2)	C27—C26—N6	118.8 (2)
C10—C5—C6	119.8 (2)	C25—C26—N6	118.1 (2)
C10—C5—C2	120.7 (2)	C26—C27—C28	117.9 (3)
C6—C5—C2	119.4 (2)	C26—C27—H27	121.1
C7—C6—C5	120.2 (3)	C28—C27—H27	121.1
C7—C6—H6	119.9	C23—C28—C27	120.1 (3)
C5—C6—H6	119.9	C23—C28—H28	120.0
C6—C7—C8	118.4 (3)	C27—C28—H28	120.0
C6—C7—H7	120.8	O7—C29—C30	121.0 (3)
C8—C7—H7	120.8	O7—C29—C21	119.2 (3)
C9—C8—C7	122.6 (2)	C30—C29—C21	119.9 (2)
C9—C8—N3	119.2 (2)	C31—C30—C35	119.2 (3)
C7—C8—N3	118.2 (3)	C31—C30—C29	123.4 (3)
C10—C9—C8	118.4 (3)	C35—C30—C29	117.5 (3)
C10—C9—H9	120.8	C32—C31—C30	120.0 (3)
C8—C9—H9	120.8	C32—C31—H31	120.0
C9—C10—C5	120.7 (3)	C30—C31—H31	120.0
C9—C10—H10	119.7	C33—C32—C31	120.3 (3)
C5—C10—H10	119.7	C33—C32—H32	119.9
O2—C11—C12	121.3 (2)	C31—C32—H32	119.9
O2—C11—C3	119.7 (3)	C34—C33—C32	120.0 (3)
C12—C11—C3	119.0 (2)	C34—C33—H33	120.0
C17—C12—C13	119.3 (3)	C32—C33—H33	120.0
C17—C12—C11	117.3 (3)	C33—C34—C35	120.4 (3)
C13—C12—C11	123.4 (2)	C33—C34—H34	119.8
C14—C13—C12	119.8 (3)	C35—C34—H34	119.8
C14—C13—H13	120.1	C34—C35—C30	120.1 (3)
C12—C13—H13	120.1	C34—C35—H35	119.9
C15—C14—C13	120.5 (4)	C30—C35—H35	120.0
C15—C14—H14	119.7	F4—C36—F6	108.0 (2)
C13—C14—H14	119.7	F4—C36—F5	107.5 (2)
C14—C15—C16	120.7 (4)	F6—C36—F5	107.1 (2)
C14—C15—H15	119.6	F4—C36—C22	112.1 (2)
C16—C15—H15	119.6	F6—C36—C22	110.6 (2)
C15—C16—C17	120.1 (3)	F5—C36—C22	111.3 (2)
C15—C16—H16	119.9	H11A—O11—H11B	105 (4)
C17—C16—H16	119.9	H12A—O12—H12B	102 (4)
C2—N2—C1—O1	175.8 (3)	C20—N5—C19—O6	178.1 (3)
C2—N2—C1—N1	−6.4 (4)	C20—N5—C19—N4	−3.9 (4)
C4—N1—C1—O1	−166.1 (2)	C22—N4—C19—O6	−165.8 (2)
C4—N1—C1—N2	16.1 (4)	C22—N4—C19—N5	16.1 (4)
C1—N2—C2—C5	144.1 (3)	C19—N5—C20—C23	141.1 (3)
C1—N2—C2—C3	25.0 (4)	C19—N5—C20—C21	21.7 (4)
N2—C2—C3—C4	−50.6 (3)	N5—C20—C21—C29	−172.7 (2)
C5—C2—C3—C4	−171.0 (2)	C23—C20—C21—C29	67.1 (3)
N2—C2—C3—C11	−175.1 (2)	N5—C20—C21—C22	−48.3 (3)
C5—C2—C3—C11	64.5 (3)	C23—C20—C21—C22	−168.5 (2)
C1—N1—C4—O5	78.2 (3)	C19—N4—C22—O10	76.4 (3)
C1—N1—C4—C3	−43.0 (3)	C19—N4—C22—C21	−44.1 (3)
C1—N1—C4—C18	−160.9 (2)	C19—N4—C22—C36	−162.0 (2)
C2—C3—C4—O5	−63.2 (2)	C29—C21—C22—O10	58.1 (3)
C11—C3—C4—O5	58.6 (3)	C20—C21—C22—O10	−63.9 (2)
C2—C3—C4—N1	59.8 (3)	C29—C21—C22—N4	−178.7 (2)
C11—C3—C4—N1	−178.4 (2)	C20—C21—C22—N4	59.3 (3)
C2—C3—C4—C18	176.1 (2)	C29—C21—C22—C36	−62.3 (3)
C11—C3—C4—C18	−62.1 (3)	C20—C21—C22—C36	175.7 (2)
N2—C2—C5—C10	136.7 (3)	N5—C20—C23—C28	135.7 (2)
C3—C2—C5—C10	−104.5 (3)	C21—C20—C23—C28	−104.9 (3)
N2—C2—C5—C6	−46.9 (3)	N5—C20—C23—C24	−47.9 (3)
C3—C2—C5—C6	71.9 (3)	C21—C20—C23—C24	71.5 (3)
C10—C5—C6—C7	1.0 (4)	C28—C23—C24—C25	0.5 (4)
C2—C5—C6—C7	−175.4 (3)	C20—C23—C24—C25	−175.8 (3)
C5—C6—C7—C8	−1.4 (4)	C23—C24—C25—C26	−2.2 (4)
C6—C7—C8—C9	0.5 (4)	C24—C25—C26—C27	1.8 (4)
C6—C7—C8—N3	−176.4 (3)	C24—C25—C26—N6	−176.5 (3)
O4—N3—C8—C9	−8.8 (4)	O8—N6—C26—C27	167.5 (3)
O3—N3—C8—C9	171.4 (3)	O9—N6—C26—C27	−15.0 (4)
O4—N3—C8—C7	168.2 (3)	O8—N6—C26—C25	−14.2 (4)
O3—N3—C8—C7	−11.5 (4)	O9—N6—C26—C25	163.4 (3)
C7—C8—C9—C10	0.9 (4)	C25—C26—C27—C28	0.3 (4)
N3—C8—C9—C10	177.8 (2)	N6—C26—C27—C28	178.5 (2)
C8—C9—C10—C5	−1.3 (4)	C24—C23—C28—C27	1.6 (4)
C6—C5—C10—C9	0.4 (4)	C20—C23—C28—C27	177.9 (2)
C2—C5—C10—C9	176.8 (2)	C26—C27—C28—C23	−2.0 (4)
C2—C3—C11—O2	58.5 (3)	C20—C21—C29—O7	55.1 (3)
C4—C3—C11—O2	−63.4 (3)	C22—C21—C29—O7	−66.9 (3)
C2—C3—C11—C12	−121.0 (3)	C20—C21—C29—C30	−124.5 (3)
C4—C3—C11—C12	117.1 (3)	C22—C21—C29—C30	113.6 (3)
O2—C11—C12—C17	14.1 (4)	O7—C29—C30—C31	−161.6 (3)
C3—C11—C12—C17	−166.4 (3)	C21—C29—C30—C31	17.9 (4)
O2—C11—C12—C13	−165.2 (3)	O7—C29—C30—C35	17.9 (4)
C3—C11—C12—C13	14.3 (4)	C21—C29—C30—C35	−162.6 (3)
C17—C12—C13—C14	−0.3 (5)	C35—C30—C31—C32	0.0 (5)
C11—C12—C13—C14	179.0 (3)	C29—C30—C31—C32	179.5 (3)
C12—C13—C14—C15	0.8 (6)	C30—C31—C32—C33	0.9 (5)
C13—C14—C15—C16	−0.1 (6)	C31—C32—C33—C34	−1.1 (6)
C14—C15—C16—C17	−1.0 (7)	C32—C33—C34—C35	0.5 (6)
C13—C12—C17—C16	−0.8 (5)	C33—C34—C35—C30	0.4 (6)
C11—C12—C17—C16	179.8 (3)	C31—C30—C35—C34	−0.6 (5)
C15—C16—C17—C12	1.5 (6)	C29—C30—C35—C34	179.9 (3)
O5—C4—C18—F2	71.4 (3)	O10—C22—C36—F4	72.3 (3)
N1—C4—C18—F2	−51.4 (3)	N4—C22—C36—F4	−51.3 (3)
C3—C4—C18—F2	−167.9 (2)	C21—C22—C36—F4	−167.9 (2)
O5—C4—C18—F3	−49.1 (3)	O10—C22—C36—F6	−48.3 (3)
N1—C4—C18—F3	−171.9 (2)	N4—C22—C36—F6	−171.9 (2)
C3—C4—C18—F3	71.6 (3)	C21—C22—C36—F6	71.5 (3)
O5—C4—C18—F1	−167.6 (2)	O10—C22—C36—F5	−167.2 (2)
N1—C4—C18—F1	69.7 (3)	N4—C22—C36—F5	69.2 (3)
C3—C4—C18—F1	−46.8 (3)	C21—C22—C36—F5	−47.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O11	0.92 (4)	2.11 (4)	2.903 (3)	144 (3)
N1—H1···O11i	0.95 (3)	2.08 (4)	3.011 (3)	167 (3)
N5—H5···O12ii	0.89 (4)	2.05 (4)	2.907 (3)	163 (3)
N4—H4···O12iii	0.85 (4)	2.17 (4)	3.019 (3)	176 (3)
O5—H5A···O6iv	0.89 (4)	1.78 (4)	2.678 (3)	178 (4)
O10—H10A···O1v	0.85 (2)	1.82 (2)	2.672 (3)	178 (4)
O12—H12A···O5	0.85 (4)	2.13 (4)	2.817 (3)	137 (3)
O12—H12A···O2	0.85 (4)	2.32 (4)	3.026 (3)	140 (3)
O11—H11A···O10vi	0.82 (4)	2.22 (4)	2.815 (3)	129 (3)
O11—H11A···O7vi	0.82 (4)	2.27 (4)	3.009 (3)	150 (3)
O11—H11B···O6vii	0.83 (4)	2.05 (4)	2.853 (3)	163 (4)
O12—H12B···O1viii	0.82 (4)	2.12 (4)	2.840 (3)	147 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O11	0.92 (4)	2.11 (4)	2.903 (3)	144 (3)
N1—H1⋯O11i	0.95 (3)	2.08 (4)	3.011 (3)	167 (3)
N5—H5⋯O12ii	0.89 (4)	2.05 (4)	2.907 (3)	163 (3)
N4—H4⋯O12iii	0.85 (4)	2.17 (4)	3.019 (3)	176 (3)
O5—H5A⋯O6iv	0.89 (4)	1.78 (4)	2.678 (3)	178 (4)
O10—H10A⋯O1v	0.85 (2)	1.82 (2)	2.672 (3)	178 (4)
O12—H12A⋯O5	0.85 (4)	2.13 (4)	2.817 (3)	137 (3)
O12—H12A⋯O2	0.85 (4)	2.32 (4)	3.026 (3)	140 (3)
O11—H11A⋯O10vi	0.82 (4)	2.22 (4)	2.815 (3)	129 (3)
O11—H11A⋯O7vi	0.82 (4)	2.27 (4)	3.009 (3)	150 (3)
O11—H11B⋯O6vii	0.83 (4)	2.05 (4)	2.853 (3)	163 (4)
O12—H12B⋯O1viii	0.82 (4)	2.12 (4)	2.840 (3)	147 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .