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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Methyl 4-(4-fluoro­phen­yl)-6-iso­propyl-2-[N-methyl-N-(methylsulfonyl)amino]­pyrimidine-5-carboxyl­ate

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technolgy, Xinmofan Road No. 5, Nanjing 210009, People's Republic of China, and bNanjing Frochem Tech. Co. Ltd, Xinmofan Road No. 36, Nanjing 210009, People's Republic of China
*Correspondence e-mail: guocheng@njut.edu.cn

(Received 23 April 2008; accepted 7 May 2008; online 21 May 2008)

In the mol­ecule of the title compound, C17H20FN3O4S, the pyrimidine and benzene rings are oriented at a dihedral angle of 35.59 (3)°. Intra­molecular C—H⋯N and C—H⋯O hydrogen bonds result in the formation of one five- and two six-membered non-planar rings. One of the six-membered rings adopts a chair conformation, while the other six-membered ring and the five-membered ring exhibit envelope conformations with O and N atoms displaced by 0.837 (3) and 0.152 (3) Å, respectively from the planes of the other ring atoms. In the crystal structure, inter­molecular C—H⋯F hydrogen bonds link the mol­ecules into infinite chains.

Related literature

For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20FN3O4S

  • Mr = 381.42

  • Orthorhombic, P n a 21

  • a = 9.886 (2) Å

  • b = 9.988 (2) Å

  • c = 18.819 (4) Å

  • V = 1858.2 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 294 (2) K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.939, Tmax = 0.979

  • 3641 measured reflections

  • 3641 independent reflections

  • 2501 reflections with I > 2σ(I)

  • 3 standard reflections frequency: 120 min intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.075

  • wR(F2) = 0.182

  • S = 1.04

  • 3641 reflections

  • 235 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.25 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1755 Friedel pairs

  • Flack parameter: 0.14 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3B⋯O1 0.98 2.52 3.181 (8) 125
C10—H10B⋯N1 0.96 2.56 3.148 (7) 120
C11—H11A⋯N2 0.96 2.23 2.697 (7) 109
C11—H11C⋯Fi 0.96 2.34 3.302 (8) 177
Symmetry code: (i) [-x+2, -y+1, z+{\script{1\over 2}}].

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Some derivatives of pyrimidine are important chemical materials. We report herein the crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1), rings A (N1/N2/C4-C7) and B (C12-C17) are, of course, planar, and the dihedral angle between them is A/B = 35.59 (3)°. The intramolecular C-H···N and C-H···O hydrogen bonds (Table 1) result in the formation of one five- and two six-membered non-planar rings: C (N2/N3/C5/C11/H11A), D (S/N1/N3/C5/C10/H10B) and E (O1/C3/C4/C7/C8/H3B), respectively. Ring D adopts chair [ϕ = -40.04 (2)° and θ = 134.72 (3)°] conformation, having total puckering amplitude, QT, of 1.188 (3) Å (Cremer & Pople, 1975). Rings C and E have envelope conformations with nitrogen and oxygen atoms displaced by 0.152 (3) Å and 0.837 (3) Å from the planes of the other ring atoms, respectively.

In the crystal structure, intermolecular C-H···F hydrogen bonds (Table 1) link the molecules into infinite chains (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

For the preparation of the title compound, sodium salt of N-methyl methane sulphonamide (106 g, 631.00 mmol) and methyl 4-(4-fluorophenyl)-6-isopropyl- 2-methyl sulfonylpyrimidine-5-carboxylate (100 g, 284.06 mmol) were added to DMF (1000 ml) in a round bottom flask, and then stirred for 1 h at 303 K. After completion of the reaction, demineralized water (1000 ml) was added and stirred for 1 h. The mixture was filtered, washed with water, and then dried (yield; 95%). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Refinement top

H atoms were positioned geometrically, with C-H = 0.93, 0.98 and 0.96 Å for aromatic, methine and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. A partial packing diagram for (I). Hydrogen bonds are shown as dashed lines.
Methyl 4-(4-fluorophenyl)-6-isopropyl-2-[N-methyl-N- (methylsulfonyl)amino]pyrimidine-5-carboxylate top
Crystal data top
C17H20FN3O4SF(000) = 800
Mr = 381.42Dx = 1.363 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 25 reflections
a = 9.886 (2) Åθ = 9–13°
b = 9.988 (2) ŵ = 0.21 mm1
c = 18.819 (4) ÅT = 294 K
V = 1858.2 (7) Å3Block, colorless
Z = 40.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2501 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
Graphite monochromatorθmax = 26.0°, θmin = 2.2°
ω/2θ scansh = 012
Absorption correction: ψ scan
(North et al., 1968)
k = 012
Tmin = 0.939, Tmax = 0.979l = 2323
3641 measured reflections3 standard reflections every 120 min
3641 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)] = 0.075H-atom parameters constrained
wR(F2) = 0.182 w = 1/[σ2(Fo2) + (0.070P)2 + 2.P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3641 reflectionsΔρmax = 0.23 e Å3
235 parametersΔρmin = 0.25 e Å3
1 restraintAbsolute structure: Flack (1983), 1755 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.14 (16)
Crystal data top
C17H20FN3O4SV = 1858.2 (7) Å3
Mr = 381.42Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 9.886 (2) ŵ = 0.21 mm1
b = 9.988 (2) ÅT = 294 K
c = 18.819 (4) Å0.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2501 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.062
Tmin = 0.939, Tmax = 0.9793 standard reflections every 120 min
3641 measured reflections intensity decay: none
3641 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.182Δρmax = 0.23 e Å3
S = 1.04Δρmin = 0.25 e Å3
3641 reflectionsAbsolute structure: Flack (1983), 1755 Friedel pairs
235 parametersAbsolute structure parameter: 0.14 (16)
1 restraint
Special details top

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 > 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) top
xyzUiso*/Ueq
S0.55906 (13)0.70239 (15)0.79080 (8)0.0491 (4)
O10.8512 (5)1.1302 (5)0.5173 (3)0.0717 (13)
O21.0367 (4)1.0166 (5)0.5494 (2)0.0611 (12)
O30.5199 (5)0.5777 (4)0.8218 (3)0.0728 (14)
O40.4566 (4)0.7948 (5)0.7692 (2)0.0672 (14)
N10.6898 (5)0.8871 (5)0.6925 (2)0.0463 (12)
N20.7773 (4)0.7113 (4)0.6207 (2)0.0396 (10)
N30.6541 (5)0.6626 (4)0.7201 (2)0.0424 (10)
F1.1194 (5)0.5725 (5)0.3523 (2)0.1013 (16)
C10.5763 (7)1.1558 (7)0.6613 (5)0.088 (3)
H1B0.55381.14250.61210.132*
H1C0.55981.24740.67400.132*
H1D0.52161.09820.69020.132*
C20.7657 (9)1.1427 (7)0.7496 (4)0.077 (2)
H2B0.85961.12130.75570.116*
H2C0.71191.08530.77920.116*
H2D0.75051.23440.76280.116*
C30.7266 (6)1.1227 (6)0.6731 (3)0.0476 (13)
H3B0.78201.18120.64310.057*
C40.7495 (6)0.9773 (5)0.6511 (3)0.0407 (12)
C50.7091 (5)0.7596 (6)0.6763 (3)0.0414 (12)
C60.8381 (5)0.8018 (5)0.5786 (3)0.0384 (11)
C70.8293 (5)0.9380 (5)0.5933 (3)0.0409 (12)
C80.9025 (6)1.0407 (6)0.5488 (3)0.0475 (13)
C91.1203 (7)1.0930 (8)0.5012 (4)0.082 (2)
H9A1.21301.06610.50640.123*
H9B1.11191.18660.51180.123*
H9C1.09161.07700.45320.123*
C100.6696 (6)0.7803 (7)0.8495 (3)0.0590 (17)
H10A0.62140.80670.89150.088*
H10B0.70800.85810.82720.088*
H10C0.74070.71930.86210.088*
C110.6988 (7)0.5213 (5)0.7138 (4)0.0561 (16)
H11A0.75290.51110.67170.084*
H11B0.62110.46400.71070.084*
H11C0.75150.49740.75470.084*
C120.9120 (6)0.7448 (6)0.5171 (3)0.0448 (13)
C130.9775 (6)0.6210 (6)0.5252 (3)0.0517 (14)
H13A0.97240.57620.56840.062*
C141.0499 (7)0.5646 (7)0.4695 (3)0.0630 (17)
H14A1.09740.48510.47560.076*
C151.0497 (7)0.6284 (7)0.4061 (4)0.0628 (18)
C160.9852 (7)0.7473 (7)0.3944 (3)0.0601 (17)
H16A0.98770.78780.34990.072*
C170.9152 (6)0.8071 (7)0.4507 (3)0.0534 (15)
H17A0.87090.88820.44380.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0363 (6)0.0583 (8)0.0528 (8)0.0070 (7)0.0064 (7)0.0028 (8)
O10.079 (3)0.059 (3)0.077 (3)0.018 (3)0.013 (3)0.031 (2)
O20.050 (2)0.082 (3)0.051 (2)0.014 (2)0.006 (2)0.012 (2)
O30.071 (3)0.062 (3)0.086 (3)0.019 (2)0.018 (3)0.009 (3)
O40.039 (2)0.073 (3)0.090 (4)0.012 (2)0.006 (2)0.012 (3)
N10.045 (3)0.046 (3)0.048 (3)0.002 (2)0.004 (2)0.003 (2)
N20.043 (2)0.031 (2)0.045 (2)0.0016 (19)0.005 (2)0.001 (2)
N30.048 (2)0.038 (2)0.041 (2)0.000 (2)0.002 (2)0.005 (2)
F0.117 (4)0.110 (3)0.076 (3)0.019 (3)0.038 (3)0.036 (3)
C10.072 (5)0.048 (4)0.143 (8)0.024 (4)0.022 (5)0.020 (5)
C20.114 (7)0.048 (4)0.070 (4)0.011 (4)0.024 (5)0.012 (3)
C30.049 (3)0.040 (3)0.054 (3)0.001 (3)0.002 (3)0.000 (3)
C40.040 (3)0.042 (3)0.040 (3)0.001 (2)0.001 (2)0.005 (2)
C50.033 (3)0.047 (3)0.044 (3)0.006 (2)0.001 (2)0.007 (3)
C60.035 (3)0.043 (3)0.038 (3)0.011 (2)0.004 (2)0.003 (2)
C70.035 (3)0.044 (3)0.044 (3)0.003 (3)0.005 (2)0.007 (2)
C80.049 (3)0.047 (3)0.047 (3)0.002 (3)0.001 (3)0.001 (3)
C90.064 (5)0.110 (7)0.072 (5)0.033 (5)0.014 (4)0.021 (5)
C100.056 (4)0.082 (5)0.039 (3)0.011 (3)0.004 (3)0.005 (3)
C110.072 (4)0.032 (3)0.064 (4)0.004 (3)0.001 (3)0.001 (3)
C120.050 (3)0.041 (3)0.043 (3)0.008 (3)0.001 (3)0.007 (3)
C130.053 (3)0.052 (3)0.051 (3)0.003 (3)0.007 (3)0.003 (3)
C140.064 (4)0.066 (4)0.059 (4)0.006 (4)0.014 (3)0.005 (3)
C150.062 (4)0.071 (4)0.055 (4)0.003 (4)0.014 (3)0.017 (4)
C160.067 (4)0.069 (4)0.044 (3)0.004 (4)0.012 (3)0.003 (3)
C170.053 (4)0.064 (4)0.044 (3)0.010 (3)0.005 (3)0.003 (3)
Geometric parameters (Å, º) top
S—O31.428 (4)C4—C71.399 (7)
S—O41.429 (4)C6—C71.392 (7)
S—N31.677 (5)C6—C121.481 (7)
S—C101.738 (6)C7—C81.509 (8)
O1—C81.187 (7)C9—H9A0.9600
O2—C81.348 (7)C9—H9B0.9600
O2—C91.446 (7)C9—H9C0.9600
N1—C41.329 (7)C10—H10A0.9600
N1—C51.324 (7)C10—H10B0.9600
N2—C51.335 (7)C10—H10C0.9600
N2—C61.345 (6)C11—H11A0.9600
N3—C51.384 (7)C11—H11B0.9600
N3—C111.483 (6)C11—H11C0.9600
F—C151.346 (7)C12—C131.404 (8)
C1—C31.538 (9)C12—C171.398 (8)
C1—H1B0.9600C13—C141.389 (8)
C1—H1C0.9600C13—H13A0.9300
C1—H1D0.9600C14—C151.353 (9)
C2—C31.505 (9)C14—H14A0.9300
C2—H2B0.9600C15—C161.366 (9)
C2—H2C0.9600C16—C171.398 (8)
C2—H2D0.9600C16—H16A0.9300
C3—C41.526 (8)C17—H17A0.9300
C3—H3B0.9800
O4—S—O3119.2 (3)C4—C7—C8120.7 (5)
O4—S—N3109.0 (3)O1—C8—O2124.0 (6)
O3—S—N3105.6 (3)O1—C8—C7125.8 (6)
O4—S—C10109.7 (3)O2—C8—C7110.2 (5)
O3—S—C10107.6 (3)O2—C9—H9A109.5
N3—S—C10104.9 (3)O2—C9—H9B109.5
C8—O2—C9117.6 (5)H9A—C9—H9B109.5
C5—N1—C4117.0 (5)O2—C9—H9C109.5
C5—N2—C6116.4 (4)H9A—C9—H9C109.5
C5—N3—C11120.1 (5)H9B—C9—H9C109.5
C5—N3—S121.8 (4)S—C10—H10A109.5
C11—N3—S117.2 (4)S—C10—H10B109.5
C3—C1—H1B109.5H10A—C10—H10B109.5
C3—C1—H1C109.5S—C10—H10C109.5
H1B—C1—H1C109.5H10A—C10—H10C109.5
C3—C1—H1D109.5H10B—C10—H10C109.5
H1B—C1—H1D109.5N3—C11—H11A109.5
H1C—C1—H1D109.5N3—C11—H11B109.5
C3—C2—H2B109.5H11A—C11—H11B109.5
C3—C2—H2C109.5N3—C11—H11C109.5
H2B—C2—H2C109.5H11A—C11—H11C109.5
C3—C2—H2D109.5H11B—C11—H11C109.5
H2B—C2—H2D109.5C17—C12—C13118.6 (5)
H2C—C2—H2D109.5C17—C12—C6122.6 (5)
C2—C3—C4110.4 (5)C13—C12—C6118.8 (5)
C2—C3—C1111.0 (6)C14—C13—C12120.9 (6)
C4—C3—C1108.0 (5)C14—C13—H13A119.6
C2—C3—H3B109.1C12—C13—H13A119.6
C4—C3—H3B109.1C15—C14—C13118.3 (7)
C1—C3—H3B109.1C15—C14—H14A120.8
N1—C4—C7121.0 (5)C13—C14—H14A120.8
N1—C4—C3114.8 (5)F—C15—C14117.8 (6)
C7—C4—C3124.2 (5)F—C15—C16118.7 (6)
N1—C5—N2126.9 (5)C14—C15—C16123.5 (6)
N1—C5—N3118.7 (5)C15—C16—C17118.8 (6)
N2—C5—N3114.3 (5)C15—C16—H16A120.6
N2—C6—C7120.8 (5)C17—C16—H16A120.6
N2—C6—C12115.0 (5)C12—C17—C16119.9 (6)
C7—C6—C12124.2 (5)C12—C17—H17A120.1
C6—C7—C4117.7 (5)C16—C17—H17A120.1
C6—C7—C8121.6 (5)
O4—S—N3—C550.2 (5)C3—C4—C7—C6178.4 (5)
O3—S—N3—C5179.3 (4)N1—C4—C7—C8176.9 (5)
C10—S—N3—C567.2 (5)C3—C4—C7—C81.4 (8)
O4—S—N3—C11141.0 (4)N2—C6—C7—C43.3 (7)
O3—S—N3—C1112.0 (5)C12—C6—C7—C4176.5 (5)
C10—S—N3—C11101.5 (5)N2—C6—C7—C8176.9 (5)
C9—O2—C8—O18.8 (9)C12—C6—C7—C83.3 (8)
C9—O2—C8—C7171.1 (5)N2—C6—C12—C17143.1 (6)
C5—N1—C4—C70.2 (8)C7—C6—C12—C1736.7 (8)
C5—N1—C4—C3178.7 (5)N2—C6—C12—C1334.7 (7)
C4—N1—C5—N23.3 (8)C7—C6—C12—C13145.5 (6)
C4—N1—C5—N3176.9 (5)C6—C7—C8—O1121.1 (7)
C6—N2—C5—N13.3 (8)C4—C7—C8—O158.6 (8)
C6—N2—C5—N3176.9 (4)C6—C7—C8—O258.8 (7)
C5—N2—C6—C70.3 (7)C4—C7—C8—O2121.5 (6)
C5—N2—C6—C12179.5 (4)C17—C12—C13—C143.2 (9)
S—N3—C5—N12.5 (7)C6—C12—C13—C14178.9 (6)
S—N3—C5—N2177.3 (4)C13—C12—C17—C161.3 (9)
C11—N3—C5—N1165.9 (5)C6—C12—C17—C16179.1 (6)
C11—N3—C5—N214.2 (7)C12—C13—C14—C153.5 (10)
C2—C3—C4—N153.8 (7)C13—C14—C15—F179.6 (6)
C1—C3—C4—N167.7 (7)C13—C14—C15—C161.9 (11)
C2—C3—C4—C7124.6 (6)C14—C15—C16—C170.1 (11)
C1—C3—C4—C7113.9 (7)F—C15—C16—C17178.6 (6)
N1—C4—C7—C63.3 (8)C15—C16—C17—C120.2 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3B···O10.982.523.181 (8)125
C10—H10B···N10.962.563.148 (7)120
C11—H11A···N20.962.232.697 (7)109
C11—H11C···Fi0.962.343.302 (8)177
Symmetry code: (i) x+2, y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H20FN3O4S
Mr381.42
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)294
a, b, c (Å)9.886 (2), 9.988 (2), 18.819 (4)
V3)1858.2 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.939, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
3641, 3641, 2501
Rint0.062
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.075, 0.182, 1.04
No. of reflections3641
No. of parameters235
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.25
Absolute structureFlack (1983), 1755 Friedel pairs
Absolute structure parameter0.14 (16)

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3B···O10.982.523.181 (8)125.00
C10—H10B···N10.962.563.148 (7)120.00
C11—H11A···N20.962.232.697 (7)109.00
C11—H11C···Fi0.962.343.302 (8)177.00
Symmetry code: (i) x+2, y+1, z+1/2.
 

References

First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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