organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

N-[5-(Di­phenyl­phosphorylmeth­yl)-4-(4-fluoro­phen­yl)-6-iso­propyl­pyrimi­din-2-yl]-N-methyl­methane­sulfonamide

aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, No. 625 Geguan Road, Dachang, Nanjing 210048, People's Republic of China
*Correspondence e-mail: adsony05@163.com

(Received 29 September 2013; accepted 15 October 2013; online 19 October 2013)

In the title compound, C28H29FN3O3PS, the pyrimidine ring is oriented at a dihedral angle of 50.9 (2)° with respect to the floro­benzene ring, while the two phenyl rings bonding to the same P atom are twisted with respect to each other, making a dihedral angle of 62.2 (2)°. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯F hydrogen bonds into a three-dimensional supra­molecular architecture.

Related literature

For the synthesis of the title compound, an inter­mediate for the preparation of the statin rosuvastation {systematic name: (3R,5S,6E)-7-[4-(4-fluoro­phen­yl)-2-(N-methyl­methane­sulfon­amido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-di­hydroxy­hept-6-enoic acid}, see: Brieden & Veith (2000[Brieden, W. & Veith, U. (2000). Eur. Patent EP1035127.]).

[Scheme 1]

Experimental

Crystal data
  • C28H29FN3O3PS

  • Mr = 537.57

  • Monoclinic, P 21 /n

  • a = 14.023 (3) Å

  • b = 6.3830 (13) Å

  • c = 30.493 (6) Å

  • β = 102.79 (3)°

  • V = 2661.7 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 293 K

  • 0.20 × 0.10 × 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 = 0.957, Tmax = 0.978

  • 5109 measured reflections

  • 4898 independent reflections

  • 2568 reflections with I > 2σ(I)

  • Rint = 0.092

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.136

  • S = 1.00

  • 4898 reflections

  • 334 parameters

  • H-atom parameters constrained

  • Δρmax = 0.29 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1B⋯O1i 0.96 2.56 3.363 (5) 141
C2—H2C⋯Fii 0.96 2.52 3.202 (6) 128
C13—H13A⋯O2iii 0.93 2.53 3.350 (6) 148
Symmetry codes: (i) [-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+2, -y, -z; (iii) x-1, y, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound is an intermediate for the preparation of rosuvastation (Brieden & Veith, 2000). We herein report its molecular and crystal structure (Fig. 1). The dihedral angles between the aromatic rings are: 30.7 (2)° (A/B), 65.76 (1)° (A/D), 50.9 (2)°(A/E), and 62.2 (2)° (B/D) [with the rings defined as: A =C3/N2/C4—C6/N3, B=C11—C16, D=C17—C22 and E=C23—C28]. In the crystal structure, no classic hydrogen bond was observed and molecules were stacked to form three-dimensional framework by weak C—H···O and C—H···F interactions (Table 1) (Fig. 2).

Related literature top

For the synthesis of the title compound, an intermediate for the preparation of the statin rosuvastation {systematic name: (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid}, see: Brieden & Veith (2000).

Experimental top

The title compound was synthesized according to a procedure published by Brieden & Veith (2000). Colorless crystals suitable for X-ray analysis were obtained by dissolving the compound (0.5 g) in ethanol (80 ml) and evaporating the solvent slowly at room temperature for about 5 d.

Refinement top

H atoms were positioned geometrically with C—H = 0.93-0.98 Å and constrained to ride on their parent atoms, Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram of (I).
N-[5-(Diphenylphosphorylmethyl)-4-(4-fluorophenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide top
Crystal data top
C28H29FN3O3PSF(000) = 1128
Mr = 537.57Dx = 1.342 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 14.023 (3) Åθ = 9–13°
b = 6.3830 (13) ŵ = 0.22 mm1
c = 30.493 (6) ÅT = 293 K
β = 102.79 (3)°Block, colorless
V = 2661.7 (9) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
2568 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.092
Graphite monochromatorθmax = 25.5°, θmin = 1.4°
ω/2θ scansh = 016
Absorption correction: ψ scan
(North et al., 1968)
k = 07
Tmin = 0.957, Tmax = 0.978l = 3635
5109 measured reflections3 standard reflections every 200 reflections
4898 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0378P)2]
where P = (Fo2 + 2Fc2)/3
4898 reflections(Δ/σ)max < 0.001
334 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C28H29FN3O3PSV = 2661.7 (9) Å3
Mr = 537.57Z = 4
Monoclinic, P21/nMo Kα radiation
a = 14.023 (3) ŵ = 0.22 mm1
b = 6.3830 (13) ÅT = 293 K
c = 30.493 (6) Å0.20 × 0.10 × 0.10 mm
β = 102.79 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
2568 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.092
Tmin = 0.957, Tmax = 0.9783 standard reflections every 200 reflections
5109 measured reflections intensity decay: 1%
4898 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.136H-atom parameters constrained
S = 1.00Δρmax = 0.29 e Å3
4898 reflectionsΔρmin = 0.26 e Å3
334 parameters
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P0.66722 (7)0.42516 (17)0.11070 (4)0.0362 (3)
S1.18096 (8)0.76834 (19)0.19108 (4)0.0487 (3)
F0.8413 (2)0.3088 (5)0.02311 (10)0.0980 (11)
O11.1845 (2)0.6427 (5)0.22969 (10)0.0686 (10)
N11.1193 (2)0.6413 (5)0.14580 (11)0.0482 (9)
C11.1139 (3)0.9950 (7)0.19474 (16)0.0659 (14)
H1B1.14591.07510.22040.099*
H1C1.04940.95760.19780.099*
H1D1.10941.07710.16800.099*
N20.9853 (2)0.5871 (5)0.17771 (10)0.0398 (8)
O21.2701 (2)0.8296 (5)0.17934 (11)0.0700 (10)
C21.1635 (4)0.6142 (9)0.10687 (15)0.0852 (18)
H2C1.11910.53920.08370.128*
H2D1.22330.53650.11570.128*
H2E1.17710.74900.09570.128*
O30.69197 (19)0.6503 (4)0.11812 (9)0.0459 (7)
N31.0068 (2)0.3895 (5)0.11488 (11)0.0397 (8)
C31.0327 (3)0.5313 (6)0.14613 (14)0.0399 (10)
C40.9008 (3)0.4874 (6)0.17684 (13)0.0361 (10)
C50.8634 (3)0.3368 (6)0.14377 (12)0.0339 (9)
C60.9213 (3)0.2883 (6)0.11349 (12)0.0341 (9)
C70.8527 (3)0.5433 (7)0.21492 (13)0.0439 (11)
H7A0.78240.51650.20500.053*
C80.8664 (4)0.7705 (7)0.22873 (16)0.0714 (15)
H8A0.83920.85830.20350.107*
H8B0.93500.80000.23870.107*
H8C0.83400.79770.25270.107*
C90.8930 (4)0.3984 (8)0.25420 (14)0.0732 (16)
H9A0.88240.25530.24460.110*
H9B0.86010.42510.27810.110*
H9C0.96180.42300.26470.110*
C100.7621 (2)0.2477 (6)0.14028 (12)0.0378 (10)
H10A0.75200.22150.17030.045*
H10B0.75690.11490.12450.045*
C110.5601 (3)0.3550 (6)0.13092 (13)0.0369 (10)
C120.5178 (3)0.5088 (7)0.15180 (14)0.0511 (12)
H12A0.54400.64320.15420.061*
C130.4366 (3)0.4668 (8)0.16934 (16)0.0672 (15)
H13A0.40860.57220.18340.081*
C140.3980 (3)0.2691 (9)0.16577 (16)0.0622 (14)
H14A0.34410.23950.17780.075*
C150.4384 (3)0.1138 (8)0.14443 (15)0.0628 (14)
H15A0.41080.01930.14150.075*
C160.5201 (3)0.1545 (7)0.12736 (14)0.0513 (12)
H16A0.54820.04840.11350.062*
C170.6458 (3)0.3547 (6)0.05202 (13)0.0346 (9)
C180.6367 (3)0.1505 (7)0.03646 (14)0.0485 (11)
H18A0.64280.04020.05680.058*
C190.6186 (3)0.1096 (7)0.00913 (15)0.0580 (13)
H19A0.61210.02800.01940.070*
C200.6103 (3)0.2717 (8)0.03926 (15)0.0582 (13)
H20A0.59860.24430.06990.070*
C210.6194 (3)0.4743 (8)0.02397 (15)0.0603 (13)
H21A0.61440.58410.04440.072*
C220.6357 (3)0.5165 (7)0.02123 (15)0.0512 (12)
H22A0.64010.65460.03120.061*
C230.8973 (3)0.1289 (6)0.07731 (14)0.0376 (10)
C240.8742 (3)0.0748 (6)0.08606 (14)0.0451 (11)
H24A0.87130.11260.11520.054*
C250.8553 (3)0.2243 (7)0.05210 (16)0.0528 (12)
H25A0.84010.36180.05800.063*
C260.8598 (3)0.1626 (8)0.00999 (17)0.0594 (13)
C270.8826 (4)0.0346 (8)0.00001 (16)0.0632 (14)
H27A0.88480.07060.02930.076*
C280.9028 (3)0.1825 (7)0.03403 (16)0.0545 (12)
H28A0.92000.31810.02770.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P0.0343 (6)0.0324 (6)0.0427 (7)0.0038 (5)0.0105 (5)0.0012 (5)
S0.0338 (6)0.0486 (7)0.0621 (8)0.0049 (5)0.0072 (5)0.0026 (6)
F0.137 (3)0.075 (2)0.091 (2)0.028 (2)0.044 (2)0.0440 (19)
O10.063 (2)0.074 (2)0.060 (2)0.0055 (18)0.0063 (16)0.0205 (19)
N10.043 (2)0.052 (2)0.055 (2)0.0140 (18)0.0212 (17)0.008 (2)
C10.054 (3)0.050 (3)0.091 (4)0.008 (3)0.011 (3)0.011 (3)
N20.0345 (19)0.042 (2)0.043 (2)0.0065 (17)0.0085 (16)0.0027 (17)
O20.0371 (17)0.066 (2)0.113 (3)0.0235 (17)0.0294 (17)0.023 (2)
C20.084 (4)0.117 (5)0.068 (4)0.044 (4)0.045 (3)0.015 (4)
O30.0514 (17)0.0305 (16)0.0556 (19)0.0095 (14)0.0112 (14)0.0055 (15)
N30.0356 (18)0.037 (2)0.049 (2)0.0030 (16)0.0144 (16)0.0024 (18)
C30.035 (2)0.041 (3)0.045 (3)0.003 (2)0.013 (2)0.003 (2)
C40.030 (2)0.040 (2)0.038 (2)0.0020 (19)0.0060 (18)0.002 (2)
C50.030 (2)0.034 (2)0.037 (2)0.0008 (19)0.0076 (17)0.001 (2)
C60.034 (2)0.025 (2)0.041 (2)0.0005 (18)0.0052 (18)0.0013 (19)
C70.039 (2)0.053 (3)0.040 (2)0.003 (2)0.010 (2)0.005 (2)
C80.085 (4)0.060 (3)0.083 (4)0.004 (3)0.048 (3)0.017 (3)
C90.091 (4)0.088 (4)0.044 (3)0.001 (3)0.022 (3)0.007 (3)
C100.038 (2)0.036 (2)0.040 (2)0.002 (2)0.0104 (18)0.001 (2)
C110.035 (2)0.036 (2)0.039 (2)0.0038 (19)0.0073 (18)0.007 (2)
C120.054 (3)0.043 (3)0.060 (3)0.000 (2)0.019 (2)0.001 (2)
C130.056 (3)0.071 (4)0.085 (4)0.010 (3)0.037 (3)0.001 (3)
C140.041 (3)0.081 (4)0.071 (4)0.004 (3)0.027 (2)0.002 (3)
C150.049 (3)0.065 (4)0.081 (4)0.022 (3)0.028 (3)0.003 (3)
C160.049 (3)0.049 (3)0.062 (3)0.008 (2)0.026 (2)0.003 (2)
C170.030 (2)0.033 (2)0.041 (2)0.0037 (18)0.0115 (18)0.005 (2)
C180.057 (3)0.043 (3)0.045 (3)0.003 (2)0.013 (2)0.001 (2)
C190.073 (3)0.046 (3)0.050 (3)0.000 (3)0.004 (2)0.007 (3)
C200.076 (3)0.060 (3)0.036 (3)0.002 (3)0.007 (2)0.005 (3)
C210.080 (4)0.053 (3)0.044 (3)0.008 (3)0.007 (3)0.011 (3)
C220.060 (3)0.035 (3)0.056 (3)0.001 (2)0.010 (2)0.006 (2)
C230.033 (2)0.037 (3)0.045 (3)0.0035 (19)0.0113 (19)0.002 (2)
C240.053 (3)0.037 (3)0.048 (3)0.005 (2)0.015 (2)0.005 (2)
C250.056 (3)0.033 (3)0.072 (3)0.002 (2)0.019 (3)0.010 (3)
C260.070 (3)0.047 (3)0.069 (4)0.011 (3)0.032 (3)0.023 (3)
C270.088 (4)0.057 (3)0.053 (3)0.012 (3)0.031 (3)0.008 (3)
C280.064 (3)0.038 (3)0.068 (3)0.008 (2)0.029 (3)0.005 (3)
Geometric parameters (Å, º) top
P—O31.484 (3)C10—H10A0.9700
P—C111.802 (4)C10—H10B0.9700
P—C171.805 (4)C11—C121.374 (5)
P—C101.826 (4)C11—C161.391 (5)
S—O11.416 (3)C12—C131.387 (5)
S—O21.428 (3)C12—H12A0.9300
S—N11.668 (3)C13—C141.368 (6)
S—C11.743 (4)C13—H13A0.9300
F—C261.357 (5)C14—C151.375 (6)
N1—C31.404 (5)C14—H14A0.9300
N1—C21.467 (5)C15—C161.384 (5)
C1—H1B0.9600C15—H15A0.9300
C1—H1C0.9600C16—H16A0.9300
C1—H1D0.9600C17—C221.381 (5)
N2—C31.334 (4)C17—C181.383 (5)
N2—C41.341 (4)C18—C191.382 (5)
C2—H2C0.9600C18—H18A0.9300
C2—H2D0.9600C19—C201.372 (6)
C2—H2E0.9600C19—H19A0.9300
N3—C31.306 (5)C20—C211.371 (6)
N3—C61.354 (4)C20—H20A0.9300
C4—C51.408 (5)C21—C221.373 (6)
C4—C71.509 (5)C21—H21A0.9300
C5—C61.393 (5)C22—H22A0.9300
C5—C101.512 (5)C23—C241.380 (5)
C6—C231.484 (5)C23—C281.382 (5)
C7—C81.511 (5)C24—C251.390 (5)
C7—C91.520 (6)C24—H24A0.9300
C7—H7A0.9800C25—C261.358 (6)
C8—H8A0.9600C25—H25A0.9300
C8—H8B0.9600C26—C271.350 (6)
C8—H8C0.9600C27—C281.385 (6)
C9—H9A0.9600C27—H27A0.9300
C9—H9B0.9600C28—H28A0.9300
C9—H9C0.9600
O3—P—C11111.91 (18)C5—C10—H10A109.3
O3—P—C17111.99 (18)P—C10—H10A109.3
C11—P—C17107.99 (17)C5—C10—H10B109.3
O3—P—C10113.90 (17)P—C10—H10B109.3
C11—P—C10104.36 (17)H10A—C10—H10B107.9
C17—P—C10106.17 (18)C12—C11—C16119.0 (4)
O1—S—O2119.5 (2)C12—C11—P117.3 (3)
O1—S—N1109.22 (19)C16—C11—P123.6 (3)
O2—S—N1104.34 (18)C11—C12—C13121.1 (4)
O1—S—C1109.7 (2)C11—C12—H12A119.5
O2—S—C1107.7 (2)C13—C12—H12A119.5
N1—S—C1105.6 (2)C14—C13—C12119.5 (4)
C3—N1—C2117.9 (3)C14—C13—H13A120.3
C3—N1—S121.9 (3)C12—C13—H13A120.3
C2—N1—S119.5 (3)C13—C14—C15120.3 (4)
S—C1—H1B109.5C13—C14—H14A119.8
S—C1—H1C109.5C15—C14—H14A119.8
H1B—C1—H1C109.5C14—C15—C16120.3 (4)
S—C1—H1D109.5C14—C15—H15A119.8
H1B—C1—H1D109.5C16—C15—H15A119.8
H1C—C1—H1D109.5C15—C16—C11119.7 (4)
C3—N2—C4116.0 (3)C15—C16—H16A120.1
N1—C2—H2C109.5C11—C16—H16A120.1
N1—C2—H2D109.5C22—C17—C18118.9 (4)
H2C—C2—H2D109.5C22—C17—P117.2 (3)
N1—C2—H2E109.5C18—C17—P123.9 (3)
H2C—C2—H2E109.5C19—C18—C17120.4 (4)
H2D—C2—H2E109.5C19—C18—H18A119.8
C3—N3—C6117.0 (3)C17—C18—H18A119.8
N3—C3—N2127.5 (4)C20—C19—C18120.1 (4)
N3—C3—N1116.3 (3)C20—C19—H19A120.0
N2—C3—N1116.2 (4)C18—C19—H19A120.0
N2—C4—C5121.7 (3)C21—C20—C19119.7 (4)
N2—C4—C7114.6 (3)C21—C20—H20A120.1
C5—C4—C7123.6 (3)C19—C20—H20A120.1
C6—C5—C4116.6 (3)C20—C21—C22120.6 (4)
C6—C5—C10123.1 (3)C20—C21—H21A119.7
C4—C5—C10120.1 (3)C22—C21—H21A119.7
N3—C6—C5121.0 (3)C21—C22—C17120.3 (4)
N3—C6—C23113.8 (3)C21—C22—H22A119.8
C5—C6—C23125.2 (3)C17—C22—H22A119.8
C4—C7—C8113.0 (3)C24—C23—C28118.9 (4)
C4—C7—C9108.1 (3)C24—C23—C6121.8 (4)
C8—C7—C9111.3 (4)C28—C23—C6119.3 (4)
C4—C7—H7A108.1C23—C24—C25121.1 (4)
C8—C7—H7A108.1C23—C24—H24A119.4
C9—C7—H7A108.1C25—C24—H24A119.4
C7—C8—H8A109.5C26—C25—C24117.6 (4)
C7—C8—H8B109.5C26—C25—H25A121.2
H8A—C8—H8B109.5C24—C25—H25A121.2
C7—C8—H8C109.5C27—C26—F119.3 (5)
H8A—C8—H8C109.5C27—C26—C25123.2 (4)
H8B—C8—H8C109.5F—C26—C25117.5 (4)
C7—C9—H9A109.5C26—C27—C28119.0 (4)
C7—C9—H9B109.5C26—C27—H27A120.5
H9A—C9—H9B109.5C28—C27—H27A120.5
C7—C9—H9C109.5C23—C28—C27120.1 (4)
H9A—C9—H9C109.5C23—C28—H28A119.9
H9B—C9—H9C109.5C27—C28—H28A119.9
C5—C10—P111.8 (3)
O1—S—N1—C342.5 (4)C17—P—C11—C1655.1 (4)
O2—S—N1—C3171.3 (3)C10—P—C11—C1657.6 (4)
C1—S—N1—C375.4 (4)C16—C11—C12—C130.2 (6)
O1—S—N1—C2127.5 (4)P—C11—C12—C13178.4 (3)
O2—S—N1—C21.3 (4)C11—C12—C13—C140.0 (7)
C1—S—N1—C2114.6 (4)C12—C13—C14—C150.9 (8)
C6—N3—C3—N21.1 (6)C13—C14—C15—C161.6 (8)
C6—N3—C3—N1177.2 (3)C14—C15—C16—C111.5 (7)
C4—N2—C3—N30.8 (6)C12—C11—C16—C150.5 (6)
C4—N2—C3—N1177.5 (3)P—C11—C16—C15179.0 (3)
C2—N1—C3—N310.0 (6)O3—P—C17—C2212.2 (4)
S—N1—C3—N3160.2 (3)C11—P—C17—C22111.5 (3)
C2—N1—C3—N2168.5 (4)C10—P—C17—C22137.1 (3)
S—N1—C3—N221.3 (5)O3—P—C17—C18169.4 (3)
C3—N2—C4—C51.6 (5)C11—P—C17—C1866.9 (4)
C3—N2—C4—C7175.9 (3)C10—P—C17—C1844.5 (4)
N2—C4—C5—C63.4 (5)C22—C17—C18—C190.5 (6)
C7—C4—C5—C6173.8 (4)P—C17—C18—C19178.9 (3)
N2—C4—C5—C10172.3 (3)C17—C18—C19—C200.5 (7)
C7—C4—C5—C1010.5 (6)C18—C19—C20—C210.4 (7)
C3—N3—C6—C51.0 (5)C19—C20—C21—C220.7 (7)
C3—N3—C6—C23179.6 (3)C20—C21—C22—C171.7 (7)
C4—C5—C6—N33.1 (5)C18—C17—C22—C211.6 (6)
C10—C5—C6—N3172.5 (3)P—C17—C22—C21179.9 (3)
C4—C5—C6—C23177.6 (3)N3—C6—C23—C24127.6 (4)
C10—C5—C6—C236.8 (6)C5—C6—C23—C2453.0 (6)
N2—C4—C7—C835.5 (5)N3—C6—C23—C2849.2 (5)
C5—C4—C7—C8147.1 (4)C5—C6—C23—C28130.2 (4)
N2—C4—C7—C988.1 (4)C28—C23—C24—C250.9 (6)
C5—C4—C7—C989.3 (5)C6—C23—C24—C25177.7 (3)
C6—C5—C10—P95.6 (4)C23—C24—C25—C260.4 (6)
C4—C5—C10—P79.9 (4)C24—C25—C26—C270.8 (7)
O3—P—C10—C533.2 (3)C24—C25—C26—F180.0 (4)
C11—P—C10—C5155.6 (3)F—C26—C27—C28179.1 (4)
C17—P—C10—C590.5 (3)C25—C26—C27—C280.1 (8)
O3—P—C11—C122.7 (4)C24—C23—C28—C271.8 (6)
C17—P—C11—C12126.4 (3)C6—C23—C28—C27178.6 (4)
C10—P—C11—C12120.9 (3)C26—C27—C28—C231.4 (7)
O3—P—C11—C16178.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O1i0.962.563.363 (5)141
C2—H2C···Fii0.962.523.202 (6)128
C13—H13A···O2iii0.932.533.350 (6)148
Symmetry codes: (i) x+5/2, y+1/2, z+1/2; (ii) x+2, y, z; (iii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O1i0.962.563.363 (5)141
C2—H2C···Fii0.962.523.202 (6)128
C13—H13A···O2iii0.932.533.350 (6)148
Symmetry codes: (i) x+5/2, y+1/2, z+1/2; (ii) x+2, y, z; (iii) x1, y, z.
 

Acknowledgements

The author thanks the Center of Testing and Analysis of Nanjing University for the data collection.

References

First citationBrieden, W. & Veith, U. (2000). Eur. Patent EP1035127.
First citationEnraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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