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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o87–o88.
Published online 2008 December 10. doi:  10.1107/S160053680804124X
PMCID: PMC2967995

5-Benzoyl-4-hydr­oxy-6-(4-nitro­phen­yl)-4-trifluoro­meth­yl-3,4,5,6-tetrahydro­pyrimidin-2(1H)-one monohydrate

Abstract

The asymmetric unit of the title compound, C18H14F3N3O5·H2O, contains two independent formula units. The two heterocyclic mol­ecules differ in the orientations of the benzoyl­phenyl group with respect to the tetra­hydro­pyrimidine ring [C—C—C—C torsion angles of 64.5 (3) and 67.1 (3)°]. In both mol­ecules the pyrimidine ring adopts a half-chair conformation. The mol­ecules 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 [triangle]); Cochran et al. (2005 [triangle]); Moran et al. (2007 [triangle]); Zorkun et al. (2006 [triangle]). For the bioactivity of organofluorine compounds, see: Hermann et al. (2003 [triangle]); Ulrich (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-00o87-scheme1.jpg

Experimental

Crystal data

  • C18H14F3N3O5·H2O
  • M r = 427.34
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-00o87-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors thank the Natural Science Foundation of Henan Province (grant No. 082300420110) and the Natural Science Foundation of Henan Province Education Department (grant No. 2007150036) for financial support.

supplementary crystallographic information

Comment

Dihydropyrimidine (DHPM) derivatives can be used as potential calcium channel blockers (Zorkun et al., 2006), inhibitors of mitotic kinesin Eg5 for treating cancer (Cochran et al., 2005; Brier et al., 2004) and as TRPA1 modulators for treating pain (Moran et al., 2007). Besides, compounds that contain fluorine have special bioactivity, for example, flumioxazin is a widely used herbicide (Hermann et al., 2003; Ulrich,2004). This led us to pay much attention to the synthesis and bioactivity of these important fused perfluoroalkylated heterocyclic compounds. During the synthesis of DHPM derivatives, the title compound, an intermediate, was isolated and confirmed by X-ray diffraction to elucidate the reaction mechanism. We report here the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig.1) contains two independent molecules which differ in the orientations of benzoylphenyl group with respect to the tetrahydropyrimidine ring. In both molecules, the pyrimidine ring adopts a half-chair conformation. The bulky substituents on the heterocyclic ring are in trans position, which must be attributed to the steric effect. The dihedral angles between C5-C10 and C12-C17 phenyl rings is 60.0 (1)° and that between C23-C28 and C30-C35 rings is 65.2 (1)°.

The crystal packing shows that the molecules are linked into a two-dimensional network parallel to the (001) by N—H···O and O—H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental

The title compound was synthesized by the reaction of 4-nitro-benzaldehyde (1 mmol), 4,4,4-trifluoro-1-phenylbutane-1,3-dione (1 mmol) and urea (1 mmol), catalyzed by 4-methylbenzenesulfonic acid, at 363 K for a certain time (monitered by TLC). After cooling, the reaction mixture was washed with water and recrystallized from ethanol, to obtain single crystals suitable for X-ray diffraction.

Refinement

N- and O-bound H atoms were located in a difference map and were refined freely except that the O10—H10A distance was restrained to 0.88 (1) Å and the Uiso for O-bound H atoms were set at 1.5Ueq(O). C-bound H atoms were placed in calculated positions (C-H = 0.95–1.00 Å) and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were averaged.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen bonds are shown as dashed lines.
Fig. 2.
The packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

C18H14F3N3O5·H2OF(000) = 1760
Mr = 427.34Dx = 1.551 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 6634 reflections
a = 14.389 (3) Åθ = 2.6–25.0°
b = 9.0391 (18) ŵ = 0.14 mm1
c = 28.141 (6) ÅT = 113 K
V = 3660.1 (13) Å3Prism, colourless
Z = 80.32 × 0.22 × 0.20 mm

Data collection

Rigaku Saturn diffractometer4437 independent reflections
Radiation source: rotating anode4222 reflections with I > 2σ(I)
confocalRint = 0.059
Detector resolution: 7.31 pixels mm-1θmax = 27.9°, θmin = 2.4°
ω scansh = −18→18
Absorption correction: multi-scan (CrystalClear, Rigaku/MSC, 2002)k = −11→10
Tmin = 0.958, Tmax = 0.973l = −36→37
28524 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0683P)2 + 0.2165P] where P = (Fo2 + 2Fc2)/3
4437 reflections(Δ/σ)max = 0.044
575 parametersΔρmax = 0.25 e Å3
2 restraintsΔρmin = −0.31 e Å3

Special details

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.

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

xyzUiso*/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)*
N20.05590 (16)0.2777 (3)0.59022 (9)0.0212 (5)
H2A0.088 (3)0.198 (4)0.5786 (14)0.032 (10)*
N30.40154 (18)0.2937 (3)0.73426 (9)0.0275 (5)
N40.17052 (16)1.1349 (2)0.98405 (8)0.0163 (4)
H40.117 (2)1.137 (3)0.9964 (13)0.021 (8)*
N50.32327 (15)1.2159 (3)0.99252 (9)0.0205 (5)
H50.364 (3)1.277 (4)1.0061 (14)0.033 (9)*
N60.66618 (17)1.2226 (3)0.84793 (9)0.0246 (5)
O1−0.06318 (13)0.1373 (2)0.56457 (7)0.0213 (4)
O20.09085 (15)0.7349 (2)0.62345 (8)0.0281 (5)
O30.38832 (18)0.2127 (3)0.76856 (9)0.0419 (6)
O40.47761 (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*
O60.20406 (14)1.35887 (19)1.01700 (7)0.0207 (4)
O70.36076 (15)0.7632 (2)0.95958 (8)0.0262 (4)
O80.64950 (18)1.2982 (3)0.81335 (9)0.0431 (6)
O90.74415 (16)1.1810 (3)0.85877 (10)0.0427 (6)
O100.21816 (13)0.9012 (2)1.01373 (7)0.0205 (4)
H10A0.1681 (18)0.889 (4)1.0294 (13)0.031*
C1−0.03449 (18)0.2551 (3)0.58280 (10)0.0172 (5)
C20.09768 (18)0.4139 (3)0.60829 (9)0.0175 (5)
H20.11850.47700.58110.021*
C30.02400 (17)0.4968 (3)0.63747 (9)0.0164 (5)
H30.01000.43730.66660.020*
C4−0.06557 (18)0.5103 (3)0.60803 (9)0.0155 (5)
C50.17991 (18)0.3796 (3)0.64030 (9)0.0180 (5)
C60.17091 (19)0.2707 (3)0.67560 (11)0.0227 (6)
H60.11530.21440.67770.027*
C70.2428 (2)0.2452 (3)0.70731 (10)0.0229 (6)
H70.23680.17330.73170.027*
C80.32376 (19)0.3271 (3)0.70250 (10)0.0200 (5)
C90.33499 (19)0.4337 (3)0.66753 (10)0.0224 (6)
H90.39150.48730.66480.027*
C100.26174 (19)0.4602 (3)0.63676 (10)0.0207 (5)
H100.26760.53420.61300.025*
C110.06423 (19)0.6473 (3)0.65320 (10)0.0191 (5)
C120.0703 (2)0.6817 (3)0.70501 (11)0.0228 (6)
C130.0605 (2)0.5753 (3)0.74055 (11)0.0296 (6)
H130.04850.47510.73240.036*
C140.0685 (3)0.6161 (4)0.78780 (13)0.0411 (8)
H140.06260.54340.81200.049*
C150.0846 (3)0.7598 (5)0.79987 (15)0.0499 (10)
H150.08980.78630.83240.060*
C160.0935 (3)0.8662 (4)0.76563 (17)0.0517 (11)
H160.10370.96630.77450.062*
C170.0875 (3)0.8281 (4)0.71771 (14)0.0361 (8)
H170.09500.90160.69390.043*
C18−0.14246 (19)0.5841 (3)0.63835 (10)0.0194 (5)
C190.23177 (18)1.2409 (3)0.99904 (10)0.0169 (5)
C200.36507 (18)1.0817 (3)0.97328 (10)0.0189 (5)
H200.38731.01760.99990.023*
C210.29152 (17)0.9978 (3)0.94407 (9)0.0161 (5)
H210.27811.05630.91470.019*
C220.20117 (18)0.9860 (3)0.97330 (9)0.0174 (5)
C230.44638 (18)1.1209 (3)0.94105 (10)0.0177 (5)
C240.43558 (19)1.2302 (3)0.90652 (11)0.0230 (6)
H240.37901.28400.90470.028*
C250.5063 (2)1.2605 (3)0.87512 (11)0.0231 (6)
H250.49861.33240.85080.028*
C260.58888 (18)1.1836 (3)0.87981 (10)0.0194 (5)
C270.60266 (19)1.0753 (3)0.91366 (10)0.0206 (5)
H270.66031.02470.91610.025*
C280.52921 (19)1.0424 (3)0.94424 (10)0.0199 (5)
H280.53580.96630.96730.024*
C290.33101 (19)0.8468 (3)0.92912 (10)0.0200 (5)
C300.3331 (2)0.8049 (3)0.87787 (11)0.0238 (6)
C310.3250 (2)0.9069 (3)0.84102 (11)0.0274 (6)
H310.31711.00900.84800.033*
C320.3284 (3)0.8593 (4)0.79407 (12)0.0364 (8)
H320.32370.92920.76900.044*
C330.3385 (3)0.7107 (4)0.78375 (14)0.0444 (9)
H330.33970.67850.75160.053*
C340.3470 (3)0.6092 (4)0.82007 (14)0.0429 (9)
H340.35440.50720.81280.052*
C350.3447 (3)0.6548 (3)0.86693 (12)0.0329 (7)
H350.35090.58430.89180.040*
C360.1248 (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)
F40.04104 (12)0.92471 (19)0.96255 (6)0.0280 (4)
F50.12020 (12)0.97358 (19)0.89937 (6)0.0278 (4)
F60.14278 (13)0.76842 (18)0.93679 (8)0.0322 (4)
O110.21603 (13)0.1296 (2)0.54929 (8)0.0212 (4)
H11A0.215 (3)0.183 (4)0.5257 (15)0.032*
H11B0.228 (3)0.046 (4)0.5390 (14)0.032*
O120.01675 (13)0.8681 (2)0.53237 (8)0.0213 (4)
H12A0.012 (2)0.807 (4)0.5554 (15)0.032*
H12B0.015 (3)0.948 (4)0.5459 (14)0.032*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0173 (11)0.0159 (10)0.0185 (10)−0.0003 (8)−0.0023 (9)−0.0037 (8)
N20.0182 (11)0.0221 (12)0.0233 (12)0.0018 (9)−0.0025 (9)−0.0082 (9)
N30.0243 (12)0.0319 (13)0.0263 (13)0.0078 (10)−0.0046 (10)−0.0066 (11)
N40.0139 (11)0.0149 (10)0.0200 (11)0.0003 (8)0.0022 (9)−0.0035 (8)
N50.0146 (10)0.0204 (11)0.0265 (13)−0.0035 (8)0.0029 (9)−0.0085 (10)
N60.0225 (12)0.0256 (11)0.0257 (13)−0.0043 (9)0.0055 (10)−0.0005 (10)
O10.0200 (9)0.0186 (9)0.0254 (10)0.0006 (7)−0.0051 (8)−0.0064 (7)
O20.0314 (11)0.0223 (9)0.0306 (12)−0.0066 (8)−0.0053 (9)0.0047 (8)
O30.0397 (14)0.0552 (15)0.0309 (13)0.0083 (11)−0.0100 (10)0.0120 (12)
O40.0212 (12)0.0774 (19)0.0542 (17)−0.0049 (12)−0.0122 (11)0.0189 (15)
O50.0198 (10)0.0227 (9)0.0162 (9)−0.0035 (7)−0.0041 (7)0.0070 (7)
O60.0205 (10)0.0172 (9)0.0246 (10)−0.0014 (7)0.0049 (8)−0.0074 (7)
O70.0313 (11)0.0257 (10)0.0217 (11)0.0099 (9)0.0031 (8)0.0039 (8)
O80.0383 (14)0.0547 (15)0.0363 (14)0.0066 (11)0.0154 (11)0.0214 (13)
O90.0190 (11)0.0639 (16)0.0453 (14)0.0005 (11)0.0045 (10)0.0152 (12)
O100.0176 (10)0.0233 (9)0.0206 (9)0.0010 (7)0.0033 (7)0.0070 (8)
C10.0186 (12)0.0169 (12)0.0161 (13)0.0005 (10)−0.0019 (10)−0.0006 (9)
C20.0157 (12)0.0177 (11)0.0191 (12)−0.0010 (9)0.0000 (9)−0.0006 (9)
C30.0161 (12)0.0171 (11)0.0159 (11)−0.0010 (9)−0.0020 (9)−0.0005 (9)
C40.0163 (12)0.0152 (11)0.0150 (11)0.0005 (9)−0.0020 (9)0.0003 (9)
C50.0179 (13)0.0175 (12)0.0187 (12)0.0005 (9)−0.0014 (10)−0.0027 (9)
C60.0165 (12)0.0248 (13)0.0267 (15)−0.0027 (10)−0.0009 (11)0.0028 (11)
C70.0249 (14)0.0238 (13)0.0200 (15)0.0072 (11)0.0004 (11)0.0026 (10)
C80.0166 (13)0.0243 (12)0.0192 (12)0.0052 (10)−0.0033 (10)−0.0051 (10)
C90.0163 (12)0.0233 (13)0.0277 (15)−0.0012 (10)−0.0008 (11)−0.0038 (11)
C100.0206 (13)0.0204 (12)0.0210 (13)−0.0002 (10)−0.0011 (10)0.0003 (10)
C110.0172 (12)0.0166 (12)0.0234 (13)−0.0005 (9)−0.0063 (10)−0.0005 (10)
C120.0225 (13)0.0210 (13)0.0249 (14)0.0008 (10)−0.0059 (11)−0.0067 (11)
C130.0373 (17)0.0302 (15)0.0214 (14)0.0032 (12)−0.0072 (12)−0.0052 (12)
C140.050 (2)0.050 (2)0.0231 (16)0.0086 (17)−0.0084 (15)−0.0097 (15)
C150.059 (3)0.064 (2)0.0273 (19)0.001 (2)−0.0115 (17)−0.0219 (18)
C160.057 (2)0.042 (2)0.056 (3)−0.0058 (17)−0.011 (2)−0.032 (2)
C170.0393 (19)0.0251 (15)0.044 (2)−0.0038 (13)−0.0058 (15)−0.0093 (14)
C180.0193 (13)0.0186 (12)0.0202 (13)−0.0016 (10)−0.0013 (10)−0.0007 (10)
C190.0183 (12)0.0168 (12)0.0156 (12)−0.0015 (10)0.0018 (10)−0.0011 (9)
C200.0171 (12)0.0204 (12)0.0193 (12)0.0002 (9)0.0039 (10)−0.0011 (10)
C210.0159 (12)0.0148 (11)0.0174 (12)−0.0002 (9)0.0012 (9)0.0012 (9)
C220.0192 (12)0.0151 (11)0.0178 (12)−0.0001 (9)0.0020 (9)0.0005 (9)
C230.0154 (13)0.0187 (12)0.0191 (12)−0.0017 (9)0.0004 (10)−0.0034 (10)
C240.0160 (12)0.0257 (13)0.0272 (15)0.0000 (10)−0.0012 (11)0.0025 (11)
C250.0219 (13)0.0239 (13)0.0234 (15)0.0018 (11)−0.0005 (11)0.0047 (11)
C260.0170 (13)0.0221 (12)0.0193 (12)−0.0040 (9)0.0022 (10)−0.0016 (10)
C270.0193 (13)0.0193 (12)0.0231 (14)0.0012 (10)0.0014 (10)−0.0004 (10)
C280.0199 (13)0.0202 (12)0.0196 (12)0.0012 (10)−0.0013 (10)−0.0012 (10)
C290.0169 (13)0.0201 (13)0.0231 (14)−0.0009 (10)0.0038 (10)−0.0012 (10)
C300.0224 (14)0.0258 (14)0.0233 (14)0.0005 (11)0.0076 (11)−0.0031 (11)
C310.0305 (16)0.0267 (14)0.0249 (15)0.0002 (12)0.0049 (12)−0.0012 (12)
C320.0425 (19)0.0447 (19)0.0221 (16)0.0049 (15)0.0058 (14)−0.0001 (14)
C330.055 (2)0.053 (2)0.0260 (18)0.0000 (17)0.0102 (16)−0.0170 (16)
C340.063 (3)0.0310 (16)0.0350 (18)0.0015 (16)0.0148 (17)−0.0141 (14)
C350.0451 (19)0.0243 (14)0.0294 (17)0.0044 (13)0.0100 (14)−0.0068 (12)
C360.0214 (14)0.0177 (12)0.0238 (13)−0.0017 (10)0.0015 (11)−0.0021 (10)
F10.0313 (9)0.0361 (9)0.0182 (8)0.0027 (7)0.0060 (7)0.0003 (7)
F20.0177 (8)0.0352 (9)0.0293 (9)0.0046 (7)−0.0009 (7)−0.0078 (7)
F30.0316 (10)0.0180 (8)0.0475 (13)0.0040 (7)0.0041 (8)−0.0103 (8)
F40.0183 (8)0.0348 (9)0.0310 (9)−0.0038 (7)0.0037 (7)−0.0104 (8)
F50.0300 (9)0.0331 (9)0.0202 (8)−0.0026 (7)−0.0041 (7)−0.0016 (7)
F60.0328 (10)0.0178 (8)0.0459 (12)−0.0009 (7)−0.0003 (8)−0.0105 (8)
O110.0228 (10)0.0166 (9)0.0242 (10)0.0021 (8)−0.0009 (8)0.0028 (8)
O120.0242 (11)0.0171 (9)0.0224 (10)0.0020 (7)0.0009 (8)0.0011 (8)

Geometric parameters (Å, °)

N1—C11.372 (3)C13—H130.95
N1—C41.452 (3)C14—C151.362 (6)
N1—H10.95 (3)C14—H140.95
N2—C11.333 (3)C15—C161.367 (7)
N2—C21.461 (3)C15—H150.95
N2—H2A0.92 (4)C16—C171.395 (6)
N3—O41.226 (4)C16—H160.95
N3—O31.226 (4)C17—H170.95
N3—C81.464 (3)C18—F21.324 (3)
N4—C191.368 (3)C18—F31.340 (3)
N4—C221.449 (3)C18—F11.341 (3)
N4—H40.85 (4)C20—C231.522 (4)
N5—C191.348 (3)C20—C211.540 (4)
N5—C201.458 (3)C20—H201.00
N5—H50.89 (4)C21—C291.537 (4)
N6—O81.213 (4)C21—C221.542 (3)
N6—O91.222 (3)C21—H211.00
N6—C261.472 (3)C22—C361.545 (4)
O1—C11.252 (3)C23—C281.390 (4)
O2—C111.214 (4)C23—C241.394 (4)
O5—C41.400 (3)C24—C251.375 (4)
O5—H5A0.89 (4)C24—H240.95
O6—C191.246 (3)C25—C261.383 (4)
O7—C291.221 (3)C25—H250.95
O10—C221.393 (3)C26—C271.380 (4)
O10—H10A0.852 (19)C27—C281.395 (4)
C2—C51.519 (4)C27—H270.95
C2—C31.536 (4)C28—H280.95
C2—H21.00C29—C301.491 (4)
C3—C41.537 (3)C30—C311.393 (4)
C3—C111.544 (4)C30—C351.401 (4)
C3—H31.00C31—C321.390 (4)
C4—C181.548 (4)C31—H310.95
C5—C101.388 (4)C32—C331.382 (5)
C5—C61.405 (4)C32—H320.95
C6—C71.385 (4)C33—C341.379 (6)
C6—H60.95C33—H330.95
C7—C81.387 (4)C34—C351.382 (5)
C7—H70.95C34—H340.95
C8—C91.387 (4)C35—H350.95
C9—C101.385 (4)C36—F41.331 (3)
C9—H90.95C36—F61.338 (3)
C10—H100.95C36—F51.343 (3)
C11—C121.493 (4)O11—H11A0.82 (4)
C12—C171.393 (4)O11—H11B0.83 (4)
C12—C131.395 (4)O12—H12A0.85 (4)
C13—C141.385 (4)O12—H12B0.82 (4)
C1—N1—C4120.7 (2)C12—C17—C16119.6 (4)
C1—N1—H1116 (2)C12—C17—H17120.2
C4—N1—H1116.9 (19)C16—C17—H17120.2
C1—N2—C2125.8 (2)F2—C18—F3107.8 (2)
C1—N2—H2A108 (2)F2—C18—F1107.5 (2)
C2—N2—H2A125 (2)F3—C18—F1106.8 (2)
O4—N3—O3122.7 (3)F2—C18—C4112.7 (2)
O4—N3—C8118.3 (3)F3—C18—C4110.3 (2)
O3—N3—C8119.0 (3)F1—C18—C4111.5 (2)
C19—N4—C22121.3 (2)O6—C19—N5120.7 (2)
C19—N4—H4117 (2)O6—C19—N4121.2 (2)
C22—N4—H4112 (2)N5—C19—N4118.0 (2)
C19—N5—C20126.3 (2)N5—C20—C23110.1 (2)
C19—N5—H5118 (3)N5—C20—C21108.9 (2)
C20—N5—H5114 (3)C23—C20—C21109.0 (2)
O8—N6—O9123.7 (3)N5—C20—H20109.6
O8—N6—C26118.3 (3)C23—C20—H20109.6
O9—N6—C26117.9 (3)C21—C20—H20109.6
C4—O5—H5A112 (2)C29—C21—C20109.2 (2)
C22—O10—H10A110 (3)C29—C21—C22113.3 (2)
O1—C1—N2121.1 (2)C20—C21—C22109.2 (2)
O1—C1—N1119.9 (2)C29—C21—H21108.3
N2—C1—N1118.9 (2)C20—C21—H21108.3
N2—C2—C5110.8 (2)C22—C21—H21108.3
N2—C2—C3108.2 (2)O10—C22—N4113.2 (2)
C5—C2—C3108.7 (2)O10—C22—C21109.0 (2)
N2—C2—H2109.7N4—C22—C21107.7 (2)
C5—C2—H2109.7O10—C22—C36110.0 (2)
C3—C2—H2109.7N4—C22—C36107.4 (2)
C2—C3—C4109.2 (2)C21—C22—C36109.5 (2)
C2—C3—C11108.9 (2)C28—C23—C24120.1 (2)
C4—C3—C11113.5 (2)C28—C23—C20120.1 (2)
C2—C3—H3108.3C24—C23—C20119.6 (2)
C4—C3—H3108.3C25—C24—C23120.4 (3)
C11—C3—H3108.3C25—C24—H24119.8
O5—C4—N1112.7 (2)C23—C24—H24119.8
O5—C4—C3109.8 (2)C24—C25—C26118.3 (3)
N1—C4—C3107.5 (2)C24—C25—H25120.8
O5—C4—C18109.7 (2)C26—C25—H25120.8
N1—C4—C18107.3 (2)C27—C26—C25123.1 (3)
C3—C4—C18109.7 (2)C27—C26—N6118.8 (2)
C10—C5—C6119.8 (2)C25—C26—N6118.1 (2)
C10—C5—C2120.7 (2)C26—C27—C28117.9 (3)
C6—C5—C2119.4 (2)C26—C27—H27121.1
C7—C6—C5120.2 (3)C28—C27—H27121.1
C7—C6—H6119.9C23—C28—C27120.1 (3)
C5—C6—H6119.9C23—C28—H28120.0
C6—C7—C8118.4 (3)C27—C28—H28120.0
C6—C7—H7120.8O7—C29—C30121.0 (3)
C8—C7—H7120.8O7—C29—C21119.2 (3)
C9—C8—C7122.6 (2)C30—C29—C21119.9 (2)
C9—C8—N3119.2 (2)C31—C30—C35119.2 (3)
C7—C8—N3118.2 (3)C31—C30—C29123.4 (3)
C10—C9—C8118.4 (3)C35—C30—C29117.5 (3)
C10—C9—H9120.8C32—C31—C30120.0 (3)
C8—C9—H9120.8C32—C31—H31120.0
C9—C10—C5120.7 (3)C30—C31—H31120.0
C9—C10—H10119.7C33—C32—C31120.3 (3)
C5—C10—H10119.7C33—C32—H32119.9
O2—C11—C12121.3 (2)C31—C32—H32119.9
O2—C11—C3119.7 (3)C34—C33—C32120.0 (3)
C12—C11—C3119.0 (2)C34—C33—H33120.0
C17—C12—C13119.3 (3)C32—C33—H33120.0
C17—C12—C11117.3 (3)C33—C34—C35120.4 (3)
C13—C12—C11123.4 (2)C33—C34—H34119.8
C14—C13—C12119.8 (3)C35—C34—H34119.8
C14—C13—H13120.1C34—C35—C30120.1 (3)
C12—C13—H13120.1C34—C35—H35119.9
C15—C14—C13120.5 (4)C30—C35—H35120.0
C15—C14—H14119.7F4—C36—F6108.0 (2)
C13—C14—H14119.7F4—C36—F5107.5 (2)
C14—C15—C16120.7 (4)F6—C36—F5107.1 (2)
C14—C15—H15119.6F4—C36—C22112.1 (2)
C16—C15—H15119.6F6—C36—C22110.6 (2)
C15—C16—C17120.1 (3)F5—C36—C22111.3 (2)
C15—C16—H16119.9H11A—O11—H11B105 (4)
C17—C16—H16119.9H12A—O12—H12B102 (4)
C2—N2—C1—O1175.8 (3)C20—N5—C19—O6178.1 (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—N216.1 (4)C22—N4—C19—N516.1 (4)
C1—N2—C2—C5144.1 (3)C19—N5—C20—C23141.1 (3)
C1—N2—C2—C325.0 (4)C19—N5—C20—C2121.7 (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—C2967.1 (3)
N2—C2—C3—C11−175.1 (2)N5—C20—C21—C22−48.3 (3)
C5—C2—C3—C1164.5 (3)C23—C20—C21—C22−168.5 (2)
C1—N1—C4—O578.2 (3)C19—N4—C22—O1076.4 (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—O1058.1 (3)
C11—C3—C4—O558.6 (3)C20—C21—C22—O10−63.9 (2)
C2—C3—C4—N159.8 (3)C29—C21—C22—N4−178.7 (2)
C11—C3—C4—N1−178.4 (2)C20—C21—C22—N459.3 (3)
C2—C3—C4—C18176.1 (2)C29—C21—C22—C36−62.3 (3)
C11—C3—C4—C18−62.1 (3)C20—C21—C22—C36175.7 (2)
N2—C2—C5—C10136.7 (3)N5—C20—C23—C28135.7 (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—C671.9 (3)C21—C20—C23—C2471.5 (3)
C10—C5—C6—C71.0 (4)C28—C23—C24—C250.5 (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—C90.5 (4)C24—C25—C26—C271.8 (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—C27167.5 (3)
O3—N3—C8—C9171.4 (3)O9—N6—C26—C27−15.0 (4)
O4—N3—C8—C7168.2 (3)O8—N6—C26—C25−14.2 (4)
O3—N3—C8—C7−11.5 (4)O9—N6—C26—C25163.4 (3)
C7—C8—C9—C100.9 (4)C25—C26—C27—C280.3 (4)
N3—C8—C9—C10177.8 (2)N6—C26—C27—C28178.5 (2)
C8—C9—C10—C5−1.3 (4)C24—C23—C28—C271.6 (4)
C6—C5—C10—C90.4 (4)C20—C23—C28—C27177.9 (2)
C2—C5—C10—C9176.8 (2)C26—C27—C28—C23−2.0 (4)
C2—C3—C11—O258.5 (3)C20—C21—C29—O755.1 (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—C12117.1 (3)C22—C21—C29—C30113.6 (3)
O2—C11—C12—C1714.1 (4)O7—C29—C30—C31−161.6 (3)
C3—C11—C12—C17−166.4 (3)C21—C29—C30—C3117.9 (4)
O2—C11—C12—C13−165.2 (3)O7—C29—C30—C3517.9 (4)
C3—C11—C12—C1314.3 (4)C21—C29—C30—C35−162.6 (3)
C17—C12—C13—C14−0.3 (5)C35—C30—C31—C320.0 (5)
C11—C12—C13—C14179.0 (3)C29—C30—C31—C32179.5 (3)
C12—C13—C14—C150.8 (6)C30—C31—C32—C330.9 (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—C350.5 (6)
C13—C12—C17—C16−0.8 (5)C33—C34—C35—C300.4 (6)
C11—C12—C17—C16179.8 (3)C31—C30—C35—C34−0.6 (5)
C15—C16—C17—C121.5 (6)C29—C30—C35—C34179.9 (3)
O5—C4—C18—F271.4 (3)O10—C22—C36—F472.3 (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—F371.6 (3)C21—C22—C36—F671.5 (3)
O5—C4—C18—F1−167.6 (2)O10—C22—C36—F5−167.2 (2)
N1—C4—C18—F169.7 (3)N4—C22—C36—F569.2 (3)
C3—C4—C18—F1−46.8 (3)C21—C22—C36—F5−47.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O110.92 (4)2.11 (4)2.903 (3)144 (3)
N1—H1···O11i0.95 (3)2.08 (4)3.011 (3)167 (3)
N5—H5···O12ii0.89 (4)2.05 (4)2.907 (3)163 (3)
N4—H4···O12iii0.85 (4)2.17 (4)3.019 (3)176 (3)
O5—H5A···O6iv0.89 (4)1.78 (4)2.678 (3)178 (4)
O10—H10A···O1v0.85 (2)1.82 (2)2.672 (3)178 (4)
O12—H12A···O50.85 (4)2.13 (4)2.817 (3)137 (3)
O12—H12A···O20.85 (4)2.32 (4)3.026 (3)140 (3)
O11—H11A···O10vi0.82 (4)2.22 (4)2.815 (3)129 (3)
O11—H11A···O7vi0.82 (4)2.27 (4)3.009 (3)150 (3)
O11—H11B···O6vii0.83 (4)2.05 (4)2.853 (3)163 (4)
O12—H12B···O1viii0.82 (4)2.12 (4)2.840 (3)147 (3)

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) −x+1/2, y+1/2, z+1/2; (iii) −x, −y+2, z+1/2; (iv) −x, −y+2, z−1/2; (v) −x, −y+1, z+1/2; (vi) −x+1/2, y−1/2, z−1/2; (vii) −x+1/2, y−3/2, z−1/2; (viii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2728).

References

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  • Moran, M. M., Fanger, C., Chong, J. A., McNamara, C., Zhen, X. G. & Mandel-Brehm, J. (2007). WO Patent No. 2 007 073 505.
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