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

Wu, Y.-M.

doi:10.1107/S1600536813028286

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1673

doi:10.1107/S1600536813028286

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

Ya-Ming Wu ^a ^*

^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.

CCDC reference: 966466

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 ).

Experimental

Crystal data

C₂₈H₂₉FN₃O₃PS
M_r = 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 ) T_min = 0.957, T_max = 0.978
5109 measured reflections
4898 independent reflections
2568 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 966466

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813028286/xu5743sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813028286/xu5743Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813028286/xu5743Isup3.cml

checkCIF report

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

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.

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

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I).

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

Crystal data top

C₂₈H₂₉FN₃O₃PS	F(000) = 1128
M_r = 537.57	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 14.023 (3) Å	θ = 9–13°
b = 6.3830 (13) Å	µ = 0.22 mm⁻¹
c = 30.493 (6) Å	T = 293 K
β = 102.79 (3)°	Block, colorless
V = 2661.7 (9) Å³	0.20 × 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 tube	R_int = 0.092
Graphite monochromator	θ_max = 25.5°, θ_min = 1.4°
ω/2θ scans	h = 0→16
Absorption correction: ψ scan (North et al., 1968)	k = 0→7
T_min = 0.957, T_max = 0.978	l = −36→35
5109 measured reflections	3 standard reflections every 200 reflections
4898 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0378P)²] where P = (F_o² + 2F_c²)/3
4898 reflections	(Δ/σ)_max < 0.001
334 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₈H₂₉FN₃O₃PS	V = 2661.7 (9) Å³
M_r = 537.57	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.023 (3) Å	µ = 0.22 mm⁻¹
b = 6.3830 (13) Å	T = 293 K
c = 30.493 (6) Å	0.20 × 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)	R_int = 0.092
T_min = 0.957, T_max = 0.978	3 standard reflections every 200 reflections
5109 measured reflections	intensity decay: 1%
4898 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.00	Δρ_max = 0.29 e Å⁻³
4898 reflections	Δρ_min = −0.26 e Å⁻³
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

	x	y	z	U_iso*/U_eq
P	0.66722 (7)	0.42516 (17)	0.11070 (4)	0.0362 (3)
S	1.18096 (8)	0.76834 (19)	0.19108 (4)	0.0487 (3)
F	0.8413 (2)	−0.3088 (5)	−0.02311 (10)	0.0980 (11)
O1	1.1845 (2)	0.6427 (5)	0.22969 (10)	0.0686 (10)
N1	1.1193 (2)	0.6413 (5)	0.14580 (11)	0.0482 (9)
C1	1.1139 (3)	0.9950 (7)	0.19474 (16)	0.0659 (14)
H1B	1.1459	1.0751	0.2204	0.099*
H1C	1.0494	0.9576	0.1978	0.099*
H1D	1.1094	1.0771	0.1680	0.099*
N2	0.9853 (2)	0.5871 (5)	0.17771 (10)	0.0398 (8)
O2	1.2701 (2)	0.8296 (5)	0.17934 (11)	0.0700 (10)
C2	1.1635 (4)	0.6142 (9)	0.10687 (15)	0.0852 (18)
H2C	1.1191	0.5392	0.0837	0.128*
H2D	1.2233	0.5365	0.1157	0.128*
H2E	1.1771	0.7490	0.0957	0.128*
O3	0.69197 (19)	0.6503 (4)	0.11812 (9)	0.0459 (7)
N3	1.0068 (2)	0.3895 (5)	0.11488 (11)	0.0397 (8)
C3	1.0327 (3)	0.5313 (6)	0.14613 (14)	0.0399 (10)
C4	0.9008 (3)	0.4874 (6)	0.17684 (13)	0.0361 (10)
C5	0.8634 (3)	0.3368 (6)	0.14377 (12)	0.0339 (9)
C6	0.9213 (3)	0.2883 (6)	0.11349 (12)	0.0341 (9)
C7	0.8527 (3)	0.5433 (7)	0.21492 (13)	0.0439 (11)
H7A	0.7824	0.5165	0.2050	0.053*
C8	0.8664 (4)	0.7705 (7)	0.22873 (16)	0.0714 (15)
H8A	0.8392	0.8583	0.2035	0.107*
H8B	0.9350	0.8000	0.2387	0.107*
H8C	0.8340	0.7977	0.2527	0.107*
C9	0.8930 (4)	0.3984 (8)	0.25420 (14)	0.0732 (16)
H9A	0.8824	0.2553	0.2446	0.110*
H9B	0.8601	0.4251	0.2781	0.110*
H9C	0.9618	0.4230	0.2647	0.110*
C10	0.7621 (2)	0.2477 (6)	0.14028 (12)	0.0378 (10)
H10A	0.7520	0.2215	0.1703	0.045*
H10B	0.7569	0.1149	0.1245	0.045*
C11	0.5601 (3)	0.3550 (6)	0.13092 (13)	0.0369 (10)
C12	0.5178 (3)	0.5088 (7)	0.15180 (14)	0.0511 (12)
H12A	0.5440	0.6432	0.1542	0.061*
C13	0.4366 (3)	0.4668 (8)	0.16934 (16)	0.0672 (15)
H13A	0.4086	0.5722	0.1834	0.081*
C14	0.3980 (3)	0.2691 (9)	0.16577 (16)	0.0622 (14)
H14A	0.3441	0.2395	0.1778	0.075*
C15	0.4384 (3)	0.1138 (8)	0.14443 (15)	0.0628 (14)
H15A	0.4108	−0.0193	0.1415	0.075*
C16	0.5201 (3)	0.1545 (7)	0.12736 (14)	0.0513 (12)
H16A	0.5482	0.0484	0.1135	0.062*
C17	0.6458 (3)	0.3547 (6)	0.05202 (13)	0.0346 (9)
C18	0.6367 (3)	0.1505 (7)	0.03646 (14)	0.0485 (11)
H18A	0.6428	0.0402	0.0568	0.058*
C19	0.6186 (3)	0.1096 (7)	−0.00913 (15)	0.0580 (13)
H19A	0.6121	−0.0280	−0.0194	0.070*
C20	0.6103 (3)	0.2717 (8)	−0.03926 (15)	0.0582 (13)
H20A	0.5986	0.2443	−0.0699	0.070*
C21	0.6194 (3)	0.4743 (8)	−0.02397 (15)	0.0603 (13)
H21A	0.6144	0.5841	−0.0444	0.072*
C22	0.6357 (3)	0.5165 (7)	0.02123 (15)	0.0512 (12)
H22A	0.6401	0.6546	0.0312	0.061*
C23	0.8973 (3)	0.1289 (6)	0.07731 (14)	0.0376 (10)
C24	0.8742 (3)	−0.0748 (6)	0.08606 (14)	0.0451 (11)
H24A	0.8713	−0.1126	0.1152	0.054*
C25	0.8553 (3)	−0.2243 (7)	0.05210 (16)	0.0528 (12)
H25A	0.8401	−0.3618	0.0580	0.063*
C26	0.8598 (3)	−0.1626 (8)	0.00999 (17)	0.0594 (13)
C27	0.8826 (4)	0.0346 (8)	−0.00001 (16)	0.0632 (14)
H27A	0.8848	0.0706	−0.0293	0.076*
C28	0.9028 (3)	0.1825 (7)	0.03403 (16)	0.0545 (12)
H28A	0.9200	0.3181	0.0277	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0343 (6)	0.0324 (6)	0.0427 (7)	−0.0038 (5)	0.0105 (5)	−0.0012 (5)
S	0.0338 (6)	0.0486 (7)	0.0621 (8)	−0.0049 (5)	0.0072 (5)	−0.0026 (6)
F	0.137 (3)	0.075 (2)	0.091 (2)	−0.028 (2)	0.044 (2)	−0.0440 (19)
O1	0.063 (2)	0.074 (2)	0.060 (2)	−0.0055 (18)	−0.0063 (16)	0.0205 (19)
N1	0.043 (2)	0.052 (2)	0.055 (2)	−0.0140 (18)	0.0212 (17)	−0.008 (2)
C1	0.054 (3)	0.050 (3)	0.091 (4)	0.008 (3)	0.011 (3)	−0.011 (3)
N2	0.0345 (19)	0.042 (2)	0.043 (2)	−0.0065 (17)	0.0085 (16)	−0.0027 (17)
O2	0.0371 (17)	0.066 (2)	0.113 (3)	−0.0235 (17)	0.0294 (17)	−0.023 (2)
C2	0.084 (4)	0.117 (5)	0.068 (4)	−0.044 (4)	0.045 (3)	−0.015 (4)
O3	0.0514 (17)	0.0305 (16)	0.0556 (19)	−0.0095 (14)	0.0112 (14)	−0.0055 (15)
N3	0.0356 (18)	0.037 (2)	0.049 (2)	−0.0030 (16)	0.0144 (16)	−0.0024 (18)
C3	0.035 (2)	0.041 (3)	0.045 (3)	−0.003 (2)	0.013 (2)	0.003 (2)
C4	0.030 (2)	0.040 (2)	0.038 (2)	0.0020 (19)	0.0060 (18)	0.002 (2)
C5	0.030 (2)	0.034 (2)	0.037 (2)	−0.0008 (19)	0.0076 (17)	0.001 (2)
C6	0.034 (2)	0.025 (2)	0.041 (2)	0.0005 (18)	0.0052 (18)	0.0013 (19)
C7	0.039 (2)	0.053 (3)	0.040 (2)	−0.003 (2)	0.010 (2)	−0.005 (2)
C8	0.085 (4)	0.060 (3)	0.083 (4)	0.004 (3)	0.048 (3)	−0.017 (3)
C9	0.091 (4)	0.088 (4)	0.044 (3)	−0.001 (3)	0.022 (3)	0.007 (3)
C10	0.038 (2)	0.036 (2)	0.040 (2)	−0.002 (2)	0.0104 (18)	0.001 (2)
C11	0.035 (2)	0.036 (2)	0.039 (2)	0.0038 (19)	0.0073 (18)	0.007 (2)
C12	0.054 (3)	0.043 (3)	0.060 (3)	0.000 (2)	0.019 (2)	−0.001 (2)
C13	0.056 (3)	0.071 (4)	0.085 (4)	0.010 (3)	0.037 (3)	−0.001 (3)
C14	0.041 (3)	0.081 (4)	0.071 (4)	−0.004 (3)	0.027 (2)	0.002 (3)
C15	0.049 (3)	0.065 (4)	0.081 (4)	−0.022 (3)	0.028 (3)	−0.003 (3)
C16	0.049 (3)	0.049 (3)	0.062 (3)	−0.008 (2)	0.026 (2)	−0.003 (2)
C17	0.030 (2)	0.033 (2)	0.041 (2)	−0.0037 (18)	0.0115 (18)	−0.005 (2)
C18	0.057 (3)	0.043 (3)	0.045 (3)	−0.003 (2)	0.013 (2)	0.001 (2)
C19	0.073 (3)	0.046 (3)	0.050 (3)	0.000 (3)	0.004 (2)	−0.007 (3)
C20	0.076 (3)	0.060 (3)	0.036 (3)	−0.002 (3)	0.007 (2)	−0.005 (3)
C21	0.080 (4)	0.053 (3)	0.044 (3)	−0.008 (3)	0.007 (3)	0.011 (3)
C22	0.060 (3)	0.035 (3)	0.056 (3)	−0.001 (2)	0.010 (2)	0.006 (2)
C23	0.033 (2)	0.037 (3)	0.045 (3)	0.0035 (19)	0.0113 (19)	−0.002 (2)
C24	0.053 (3)	0.037 (3)	0.048 (3)	0.005 (2)	0.015 (2)	0.005 (2)
C25	0.056 (3)	0.033 (3)	0.072 (3)	−0.002 (2)	0.019 (3)	−0.010 (3)
C26	0.070 (3)	0.047 (3)	0.069 (4)	−0.011 (3)	0.032 (3)	−0.023 (3)
C27	0.088 (4)	0.057 (3)	0.053 (3)	−0.012 (3)	0.031 (3)	−0.008 (3)
C28	0.064 (3)	0.038 (3)	0.068 (3)	−0.008 (2)	0.029 (3)	−0.005 (3)

Geometric parameters (Å, º) top

P—O3	1.484 (3)	C10—H10A	0.9700
P—C11	1.802 (4)	C10—H10B	0.9700
P—C17	1.805 (4)	C11—C12	1.374 (5)
P—C10	1.826 (4)	C11—C16	1.391 (5)
S—O1	1.416 (3)	C12—C13	1.387 (5)
S—O2	1.428 (3)	C12—H12A	0.9300
S—N1	1.668 (3)	C13—C14	1.368 (6)
S—C1	1.743 (4)	C13—H13A	0.9300
F—C26	1.357 (5)	C14—C15	1.375 (6)
N1—C3	1.404 (5)	C14—H14A	0.9300
N1—C2	1.467 (5)	C15—C16	1.384 (5)
C1—H1B	0.9600	C15—H15A	0.9300
C1—H1C	0.9600	C16—H16A	0.9300
C1—H1D	0.9600	C17—C22	1.381 (5)
N2—C3	1.334 (4)	C17—C18	1.383 (5)
N2—C4	1.341 (4)	C18—C19	1.382 (5)
C2—H2C	0.9600	C18—H18A	0.9300
C2—H2D	0.9600	C19—C20	1.372 (6)
C2—H2E	0.9600	C19—H19A	0.9300
N3—C3	1.306 (5)	C20—C21	1.371 (6)
N3—C6	1.354 (4)	C20—H20A	0.9300
C4—C5	1.408 (5)	C21—C22	1.373 (6)
C4—C7	1.509 (5)	C21—H21A	0.9300
C5—C6	1.393 (5)	C22—H22A	0.9300
C5—C10	1.512 (5)	C23—C24	1.380 (5)
C6—C23	1.484 (5)	C23—C28	1.382 (5)
C7—C8	1.511 (5)	C24—C25	1.390 (5)
C7—C9	1.520 (6)	C24—H24A	0.9300
C7—H7A	0.9800	C25—C26	1.358 (6)
C8—H8A	0.9600	C25—H25A	0.9300
C8—H8B	0.9600	C26—C27	1.350 (6)
C8—H8C	0.9600	C27—C28	1.385 (6)
C9—H9A	0.9600	C27—H27A	0.9300
C9—H9B	0.9600	C28—H28A	0.9300
C9—H9C	0.9600

O3—P—C11	111.91 (18)	C5—C10—H10A	109.3
O3—P—C17	111.99 (18)	P—C10—H10A	109.3
C11—P—C17	107.99 (17)	C5—C10—H10B	109.3
O3—P—C10	113.90 (17)	P—C10—H10B	109.3
C11—P—C10	104.36 (17)	H10A—C10—H10B	107.9
C17—P—C10	106.17 (18)	C12—C11—C16	119.0 (4)
O1—S—O2	119.5 (2)	C12—C11—P	117.3 (3)
O1—S—N1	109.22 (19)	C16—C11—P	123.6 (3)
O2—S—N1	104.34 (18)	C11—C12—C13	121.1 (4)
O1—S—C1	109.7 (2)	C11—C12—H12A	119.5
O2—S—C1	107.7 (2)	C13—C12—H12A	119.5
N1—S—C1	105.6 (2)	C14—C13—C12	119.5 (4)
C3—N1—C2	117.9 (3)	C14—C13—H13A	120.3
C3—N1—S	121.9 (3)	C12—C13—H13A	120.3
C2—N1—S	119.5 (3)	C13—C14—C15	120.3 (4)
S—C1—H1B	109.5	C13—C14—H14A	119.8
S—C1—H1C	109.5	C15—C14—H14A	119.8
H1B—C1—H1C	109.5	C14—C15—C16	120.3 (4)
S—C1—H1D	109.5	C14—C15—H15A	119.8
H1B—C1—H1D	109.5	C16—C15—H15A	119.8
H1C—C1—H1D	109.5	C15—C16—C11	119.7 (4)
C3—N2—C4	116.0 (3)	C15—C16—H16A	120.1
N1—C2—H2C	109.5	C11—C16—H16A	120.1
N1—C2—H2D	109.5	C22—C17—C18	118.9 (4)
H2C—C2—H2D	109.5	C22—C17—P	117.2 (3)
N1—C2—H2E	109.5	C18—C17—P	123.9 (3)
H2C—C2—H2E	109.5	C19—C18—C17	120.4 (4)
H2D—C2—H2E	109.5	C19—C18—H18A	119.8
C3—N3—C6	117.0 (3)	C17—C18—H18A	119.8
N3—C3—N2	127.5 (4)	C20—C19—C18	120.1 (4)
N3—C3—N1	116.3 (3)	C20—C19—H19A	120.0
N2—C3—N1	116.2 (4)	C18—C19—H19A	120.0
N2—C4—C5	121.7 (3)	C21—C20—C19	119.7 (4)
N2—C4—C7	114.6 (3)	C21—C20—H20A	120.1
C5—C4—C7	123.6 (3)	C19—C20—H20A	120.1
C6—C5—C4	116.6 (3)	C20—C21—C22	120.6 (4)
C6—C5—C10	123.1 (3)	C20—C21—H21A	119.7
C4—C5—C10	120.1 (3)	C22—C21—H21A	119.7
N3—C6—C5	121.0 (3)	C21—C22—C17	120.3 (4)
N3—C6—C23	113.8 (3)	C21—C22—H22A	119.8
C5—C6—C23	125.2 (3)	C17—C22—H22A	119.8
C4—C7—C8	113.0 (3)	C24—C23—C28	118.9 (4)
C4—C7—C9	108.1 (3)	C24—C23—C6	121.8 (4)
C8—C7—C9	111.3 (4)	C28—C23—C6	119.3 (4)
C4—C7—H7A	108.1	C23—C24—C25	121.1 (4)
C8—C7—H7A	108.1	C23—C24—H24A	119.4
C9—C7—H7A	108.1	C25—C24—H24A	119.4
C7—C8—H8A	109.5	C26—C25—C24	117.6 (4)
C7—C8—H8B	109.5	C26—C25—H25A	121.2
H8A—C8—H8B	109.5	C24—C25—H25A	121.2
C7—C8—H8C	109.5	C27—C26—F	119.3 (5)
H8A—C8—H8C	109.5	C27—C26—C25	123.2 (4)
H8B—C8—H8C	109.5	F—C26—C25	117.5 (4)
C7—C9—H9A	109.5	C26—C27—C28	119.0 (4)
C7—C9—H9B	109.5	C26—C27—H27A	120.5
H9A—C9—H9B	109.5	C28—C27—H27A	120.5
C7—C9—H9C	109.5	C23—C28—C27	120.1 (4)
H9A—C9—H9C	109.5	C23—C28—H28A	119.9
H9B—C9—H9C	109.5	C27—C28—H28A	119.9
C5—C10—P	111.8 (3)

O1—S—N1—C3	42.5 (4)	C17—P—C11—C16	55.1 (4)
O2—S—N1—C3	171.3 (3)	C10—P—C11—C16	−57.6 (4)
C1—S—N1—C3	−75.4 (4)	C16—C11—C12—C13	0.2 (6)
O1—S—N1—C2	−127.5 (4)	P—C11—C12—C13	−178.4 (3)
O2—S—N1—C2	1.3 (4)	C11—C12—C13—C14	0.0 (7)
C1—S—N1—C2	114.6 (4)	C12—C13—C14—C15	−0.9 (8)
C6—N3—C3—N2	1.1 (6)	C13—C14—C15—C16	1.6 (8)
C6—N3—C3—N1	−177.2 (3)	C14—C15—C16—C11	−1.5 (7)
C4—N2—C3—N3	−0.8 (6)	C12—C11—C16—C15	0.5 (6)
C4—N2—C3—N1	177.5 (3)	P—C11—C16—C15	179.0 (3)
C2—N1—C3—N3	10.0 (6)	O3—P—C17—C22	−12.2 (4)
S—N1—C3—N3	−160.2 (3)	C11—P—C17—C22	111.5 (3)
C2—N1—C3—N2	−168.5 (4)	C10—P—C17—C22	−137.1 (3)
S—N1—C3—N2	21.3 (5)	O3—P—C17—C18	169.4 (3)
C3—N2—C4—C5	−1.6 (5)	C11—P—C17—C18	−66.9 (4)
C3—N2—C4—C7	175.9 (3)	C10—P—C17—C18	44.5 (4)
N2—C4—C5—C6	3.4 (5)	C22—C17—C18—C19	0.5 (6)
C7—C4—C5—C6	−173.8 (4)	P—C17—C18—C19	178.9 (3)
N2—C4—C5—C10	−172.3 (3)	C17—C18—C19—C20	0.5 (7)
C7—C4—C5—C10	10.5 (6)	C18—C19—C20—C21	−0.4 (7)
C3—N3—C6—C5	1.0 (5)	C19—C20—C21—C22	−0.7 (7)
C3—N3—C6—C23	−179.6 (3)	C20—C21—C22—C17	1.7 (7)
C4—C5—C6—N3	−3.1 (5)	C18—C17—C22—C21	−1.6 (6)
C10—C5—C6—N3	172.5 (3)	P—C17—C22—C21	179.9 (3)
C4—C5—C6—C23	177.6 (3)	N3—C6—C23—C24	127.6 (4)
C10—C5—C6—C23	−6.8 (6)	C5—C6—C23—C24	−53.0 (6)
N2—C4—C7—C8	35.5 (5)	N3—C6—C23—C28	−49.2 (5)
C5—C4—C7—C8	−147.1 (4)	C5—C6—C23—C28	130.2 (4)
N2—C4—C7—C9	−88.1 (4)	C28—C23—C24—C25	−0.9 (6)
C5—C4—C7—C9	89.3 (5)	C6—C23—C24—C25	−177.7 (3)
C6—C5—C10—P	−95.6 (4)	C23—C24—C25—C26	−0.4 (6)
C4—C5—C10—P	79.9 (4)	C24—C25—C26—C27	0.8 (7)
O3—P—C10—C5	−33.2 (3)	C24—C25—C26—F	180.0 (4)
C11—P—C10—C5	−155.6 (3)	F—C26—C27—C28	−179.1 (4)
C17—P—C10—C5	90.5 (3)	C25—C26—C27—C28	0.1 (8)
O3—P—C11—C12	−2.7 (4)	C24—C23—C28—C27	1.8 (6)
C17—P—C11—C12	−126.4 (3)	C6—C23—C28—C27	178.6 (4)
C10—P—C11—C12	120.9 (3)	C26—C27—C28—C23	−1.4 (7)
O3—P—C11—C16	178.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+5/2, y+1/2, −z+1/2; (ii) −x+2, −y, −z; (iii) x−1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+5/2, y+1/2, −z+1/2; (ii) −x+2, −y, −z; (iii) x−1, y, z.

Acknowledgements

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

References

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

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Volume 69| Part 11| November 2013| Page o1673

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

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