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

He, W.; Yang, D.-L.; Cui, Y.-T.; Xu, Y.-M.; Guo, C.

doi:10.1107/S1600536808013524

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1126

doi:10.1107/S1600536808013524

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

Wei He,^a Dong-Ling Yang,^b Yong-Tao Cui,^a Ye-Ming Xu ^a and Cheng Guo ^a ^*

^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 ).

Experimental

Crystal data

C₁₇H₂₀FN₃O₄S
M_r = 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 ) T_min = 0.939, T_max = 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
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1755 Friedel pairs
Flack parameter: 0.14 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: CAD-4 Software; 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).

Supporting information

Crystal structure: contains datablocks D, I. DOI: 10.1107/S1600536808013524/hk2456sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013524/hk2456Isup2.hkl

checkCIF report

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, Q_T, 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.

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

	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.
	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

C₁₇H₂₀FN₃O₄S	F(000) = 800
M_r = 381.42	D_x = 1.363 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 25 reflections
a = 9.886 (2) Å	θ = 9–13°
b = 9.988 (2) Å	µ = 0.21 mm⁻¹
c = 18.819 (4) Å	T = 294 K
V = 1858.2 (7) Å³	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2501 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.062
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
T_min = 0.939, T_max = 0.979	l = −23→23
3641 measured reflections	3 standard reflections every 120 min
3641 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.075	H-atom parameters constrained
wR(F²) = 0.182	w = 1/[σ²(F_o²) + (0.070P)² + 2.P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3641 reflections	Δρ_max = 0.23 e Å⁻³
235 parameters	Δρ_min = −0.25 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1755 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.14 (16)

Crystal data top

C₁₇H₂₀FN₃O₄S	V = 1858.2 (7) Å³
M_r = 381.42	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 9.886 (2) Å	µ = 0.21 mm⁻¹
b = 9.988 (2) Å	T = 294 K
c = 18.819 (4) Å	0.30 × 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)	R_int = 0.062
T_min = 0.939, T_max = 0.979	3 standard reflections every 120 min
3641 measured reflections	intensity decay: none
3641 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	H-atom parameters constrained
wR(F²) = 0.182	Δρ_max = 0.23 e Å⁻³
S = 1.04	Δρ_min = −0.25 e Å⁻³
3641 reflections	Absolute structure: Flack (1983), 1755 Friedel pairs
235 parameters	Absolute 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

	x	y	z	U_iso*/U_eq
S	0.55906 (13)	0.70239 (15)	0.79080 (8)	0.0491 (4)
O1	0.8512 (5)	1.1302 (5)	0.5173 (3)	0.0717 (13)
O2	1.0367 (4)	1.0166 (5)	0.5494 (2)	0.0611 (12)
O3	0.5199 (5)	0.5777 (4)	0.8218 (3)	0.0728 (14)
O4	0.4566 (4)	0.7948 (5)	0.7692 (2)	0.0672 (14)
N1	0.6898 (5)	0.8871 (5)	0.6925 (2)	0.0463 (12)
N2	0.7773 (4)	0.7113 (4)	0.6207 (2)	0.0396 (10)
N3	0.6541 (5)	0.6626 (4)	0.7201 (2)	0.0424 (10)
F	1.1194 (5)	0.5725 (5)	0.3523 (2)	0.1013 (16)
C1	0.5763 (7)	1.1558 (7)	0.6613 (5)	0.088 (3)
H1B	0.5538	1.1425	0.6121	0.132*
H1C	0.5598	1.2474	0.6740	0.132*
H1D	0.5216	1.0982	0.6902	0.132*
C2	0.7657 (9)	1.1427 (7)	0.7496 (4)	0.077 (2)
H2B	0.8596	1.1213	0.7557	0.116*
H2C	0.7119	1.0853	0.7792	0.116*
H2D	0.7505	1.2344	0.7628	0.116*
C3	0.7266 (6)	1.1227 (6)	0.6731 (3)	0.0476 (13)
H3B	0.7820	1.1812	0.6431	0.057*
C4	0.7495 (6)	0.9773 (5)	0.6511 (3)	0.0407 (12)
C5	0.7091 (5)	0.7596 (6)	0.6763 (3)	0.0414 (12)
C6	0.8381 (5)	0.8018 (5)	0.5786 (3)	0.0384 (11)
C7	0.8293 (5)	0.9380 (5)	0.5933 (3)	0.0409 (12)
C8	0.9025 (6)	1.0407 (6)	0.5488 (3)	0.0475 (13)
C9	1.1203 (7)	1.0930 (8)	0.5012 (4)	0.082 (2)
H9A	1.2130	1.0661	0.5064	0.123*
H9B	1.1119	1.1866	0.5118	0.123*
H9C	1.0916	1.0770	0.4532	0.123*
C10	0.6696 (6)	0.7803 (7)	0.8495 (3)	0.0590 (17)
H10A	0.6214	0.8067	0.8915	0.088*
H10B	0.7080	0.8581	0.8272	0.088*
H10C	0.7407	0.7193	0.8621	0.088*
C11	0.6988 (7)	0.5213 (5)	0.7138 (4)	0.0561 (16)
H11A	0.7529	0.5111	0.6717	0.084*
H11B	0.6211	0.4640	0.7107	0.084*
H11C	0.7515	0.4974	0.7547	0.084*
C12	0.9120 (6)	0.7448 (6)	0.5171 (3)	0.0448 (13)
C13	0.9775 (6)	0.6210 (6)	0.5252 (3)	0.0517 (14)
H13A	0.9724	0.5762	0.5684	0.062*
C14	1.0499 (7)	0.5646 (7)	0.4695 (3)	0.0630 (17)
H14A	1.0974	0.4851	0.4756	0.076*
C15	1.0497 (7)	0.6284 (7)	0.4061 (4)	0.0628 (18)
C16	0.9852 (7)	0.7473 (7)	0.3944 (3)	0.0601 (17)
H16A	0.9877	0.7878	0.3499	0.072*
C17	0.9152 (6)	0.8071 (7)	0.4507 (3)	0.0534 (15)
H17A	0.8709	0.8882	0.4438	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0363 (6)	0.0583 (8)	0.0528 (8)	−0.0070 (7)	0.0064 (7)	0.0028 (8)
O1	0.079 (3)	0.059 (3)	0.077 (3)	0.018 (3)	0.013 (3)	0.031 (2)
O2	0.050 (2)	0.082 (3)	0.051 (2)	−0.014 (2)	0.006 (2)	0.012 (2)
O3	0.071 (3)	0.062 (3)	0.086 (3)	−0.019 (2)	0.018 (3)	0.009 (3)
O4	0.039 (2)	0.073 (3)	0.090 (4)	0.012 (2)	0.006 (2)	0.012 (3)
N1	0.045 (3)	0.046 (3)	0.048 (3)	0.002 (2)	0.004 (2)	−0.003 (2)
N2	0.043 (2)	0.031 (2)	0.045 (2)	0.0016 (19)	−0.005 (2)	−0.001 (2)
N3	0.048 (2)	0.038 (2)	0.041 (2)	0.000 (2)	0.002 (2)	0.005 (2)
F	0.117 (4)	0.110 (3)	0.076 (3)	0.019 (3)	0.038 (3)	−0.036 (3)
C1	0.072 (5)	0.048 (4)	0.143 (8)	0.024 (4)	−0.022 (5)	−0.020 (5)
C2	0.114 (7)	0.048 (4)	0.070 (4)	0.011 (4)	−0.024 (5)	−0.012 (3)
C3	0.049 (3)	0.040 (3)	0.054 (3)	−0.001 (3)	0.002 (3)	0.000 (3)
C4	0.040 (3)	0.042 (3)	0.040 (3)	−0.001 (2)	−0.001 (2)	0.005 (2)
C5	0.033 (3)	0.047 (3)	0.044 (3)	0.006 (2)	−0.001 (2)	0.007 (3)
C6	0.035 (3)	0.043 (3)	0.038 (3)	0.011 (2)	−0.004 (2)	0.003 (2)
C7	0.035 (3)	0.044 (3)	0.044 (3)	0.003 (3)	−0.005 (2)	0.007 (2)
C8	0.049 (3)	0.047 (3)	0.047 (3)	0.002 (3)	0.001 (3)	0.001 (3)
C9	0.064 (5)	0.110 (7)	0.072 (5)	−0.033 (5)	0.014 (4)	0.021 (5)
C10	0.056 (4)	0.082 (5)	0.039 (3)	−0.011 (3)	0.004 (3)	−0.005 (3)
C11	0.072 (4)	0.032 (3)	0.064 (4)	0.004 (3)	0.001 (3)	−0.001 (3)
C12	0.050 (3)	0.041 (3)	0.043 (3)	0.008 (3)	0.001 (3)	−0.007 (3)
C13	0.053 (3)	0.052 (3)	0.051 (3)	0.003 (3)	0.007 (3)	−0.003 (3)
C14	0.064 (4)	0.066 (4)	0.059 (4)	0.006 (4)	0.014 (3)	−0.005 (3)
C15	0.062 (4)	0.071 (4)	0.055 (4)	−0.003 (4)	0.014 (3)	−0.017 (4)
C16	0.067 (4)	0.069 (4)	0.044 (3)	0.004 (4)	0.012 (3)	−0.003 (3)
C17	0.053 (4)	0.064 (4)	0.044 (3)	0.010 (3)	0.005 (3)	−0.003 (3)

Geometric parameters (Å, º) top

S—O3	1.428 (4)	C4—C7	1.399 (7)
S—O4	1.429 (4)	C6—C7	1.392 (7)
S—N3	1.677 (5)	C6—C12	1.481 (7)
S—C10	1.738 (6)	C7—C8	1.509 (8)
O1—C8	1.187 (7)	C9—H9A	0.9600
O2—C8	1.348 (7)	C9—H9B	0.9600
O2—C9	1.446 (7)	C9—H9C	0.9600
N1—C4	1.329 (7)	C10—H10A	0.9600
N1—C5	1.324 (7)	C10—H10B	0.9600
N2—C5	1.335 (7)	C10—H10C	0.9600
N2—C6	1.345 (6)	C11—H11A	0.9600
N3—C5	1.384 (7)	C11—H11B	0.9600
N3—C11	1.483 (6)	C11—H11C	0.9600
F—C15	1.346 (7)	C12—C13	1.404 (8)
C1—C3	1.538 (9)	C12—C17	1.398 (8)
C1—H1B	0.9600	C13—C14	1.389 (8)
C1—H1C	0.9600	C13—H13A	0.9300
C1—H1D	0.9600	C14—C15	1.353 (9)
C2—C3	1.505 (9)	C14—H14A	0.9300
C2—H2B	0.9600	C15—C16	1.366 (9)
C2—H2C	0.9600	C16—C17	1.398 (8)
C2—H2D	0.9600	C16—H16A	0.9300
C3—C4	1.526 (8)	C17—H17A	0.9300
C3—H3B	0.9800

O4—S—O3	119.2 (3)	C4—C7—C8	120.7 (5)
O4—S—N3	109.0 (3)	O1—C8—O2	124.0 (6)
O3—S—N3	105.6 (3)	O1—C8—C7	125.8 (6)
O4—S—C10	109.7 (3)	O2—C8—C7	110.2 (5)
O3—S—C10	107.6 (3)	O2—C9—H9A	109.5
N3—S—C10	104.9 (3)	O2—C9—H9B	109.5
C8—O2—C9	117.6 (5)	H9A—C9—H9B	109.5
C5—N1—C4	117.0 (5)	O2—C9—H9C	109.5
C5—N2—C6	116.4 (4)	H9A—C9—H9C	109.5
C5—N3—C11	120.1 (5)	H9B—C9—H9C	109.5
C5—N3—S	121.8 (4)	S—C10—H10A	109.5
C11—N3—S	117.2 (4)	S—C10—H10B	109.5
C3—C1—H1B	109.5	H10A—C10—H10B	109.5
C3—C1—H1C	109.5	S—C10—H10C	109.5
H1B—C1—H1C	109.5	H10A—C10—H10C	109.5
C3—C1—H1D	109.5	H10B—C10—H10C	109.5
H1B—C1—H1D	109.5	N3—C11—H11A	109.5
H1C—C1—H1D	109.5	N3—C11—H11B	109.5
C3—C2—H2B	109.5	H11A—C11—H11B	109.5
C3—C2—H2C	109.5	N3—C11—H11C	109.5
H2B—C2—H2C	109.5	H11A—C11—H11C	109.5
C3—C2—H2D	109.5	H11B—C11—H11C	109.5
H2B—C2—H2D	109.5	C17—C12—C13	118.6 (5)
H2C—C2—H2D	109.5	C17—C12—C6	122.6 (5)
C2—C3—C4	110.4 (5)	C13—C12—C6	118.8 (5)
C2—C3—C1	111.0 (6)	C14—C13—C12	120.9 (6)
C4—C3—C1	108.0 (5)	C14—C13—H13A	119.6
C2—C3—H3B	109.1	C12—C13—H13A	119.6
C4—C3—H3B	109.1	C15—C14—C13	118.3 (7)
C1—C3—H3B	109.1	C15—C14—H14A	120.8
N1—C4—C7	121.0 (5)	C13—C14—H14A	120.8
N1—C4—C3	114.8 (5)	F—C15—C14	117.8 (6)
C7—C4—C3	124.2 (5)	F—C15—C16	118.7 (6)
N1—C5—N2	126.9 (5)	C14—C15—C16	123.5 (6)
N1—C5—N3	118.7 (5)	C15—C16—C17	118.8 (6)
N2—C5—N3	114.3 (5)	C15—C16—H16A	120.6
N2—C6—C7	120.8 (5)	C17—C16—H16A	120.6
N2—C6—C12	115.0 (5)	C12—C17—C16	119.9 (6)
C7—C6—C12	124.2 (5)	C12—C17—H17A	120.1
C6—C7—C4	117.7 (5)	C16—C17—H17A	120.1
C6—C7—C8	121.6 (5)

O4—S—N3—C5	50.2 (5)	C3—C4—C7—C6	−178.4 (5)
O3—S—N3—C5	179.3 (4)	N1—C4—C7—C8	−176.9 (5)
C10—S—N3—C5	−67.2 (5)	C3—C4—C7—C8	1.4 (8)
O4—S—N3—C11	−141.0 (4)	N2—C6—C7—C4	−3.3 (7)
O3—S—N3—C11	−12.0 (5)	C12—C6—C7—C4	176.5 (5)
C10—S—N3—C11	101.5 (5)	N2—C6—C7—C8	176.9 (5)
C9—O2—C8—O1	−8.8 (9)	C12—C6—C7—C8	−3.3 (8)
C9—O2—C8—C7	171.1 (5)	N2—C6—C12—C17	143.1 (6)
C5—N1—C4—C7	−0.2 (8)	C7—C6—C12—C17	−36.7 (8)
C5—N1—C4—C3	−178.7 (5)	N2—C6—C12—C13	−34.7 (7)
C4—N1—C5—N2	−3.3 (8)	C7—C6—C12—C13	145.5 (6)
C4—N1—C5—N3	176.9 (5)	C6—C7—C8—O1	121.1 (7)
C6—N2—C5—N1	3.3 (8)	C4—C7—C8—O1	−58.6 (8)
C6—N2—C5—N3	−176.9 (4)	C6—C7—C8—O2	−58.8 (7)
C5—N2—C6—C7	0.3 (7)	C4—C7—C8—O2	121.5 (6)
C5—N2—C6—C12	−179.5 (4)	C17—C12—C13—C14	3.2 (9)
S—N3—C5—N1	2.5 (7)	C6—C12—C13—C14	−178.9 (6)
S—N3—C5—N2	−177.3 (4)	C13—C12—C17—C16	−1.3 (9)
C11—N3—C5—N1	−165.9 (5)	C6—C12—C17—C16	−179.1 (6)
C11—N3—C5—N2	14.2 (7)	C12—C13—C14—C15	−3.5 (10)
C2—C3—C4—N1	53.8 (7)	C13—C14—C15—F	−179.6 (6)
C1—C3—C4—N1	−67.7 (7)	C13—C14—C15—C16	1.9 (11)
C2—C3—C4—C7	−124.6 (6)	C14—C15—C16—C17	−0.1 (11)
C1—C3—C4—C7	113.9 (7)	F—C15—C16—C17	−178.6 (6)
N1—C4—C7—C6	3.3 (8)	C15—C16—C17—C12	−0.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀FN₃O₄S
M_r	381.42
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	294
a, b, c (Å)	9.886 (2), 9.988 (2), 18.819 (4)
V (Å³)	1858.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.939, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	3641, 3641, 2501
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.182, 1.04
No. of reflections	3641
No. of parameters	235
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.25
Absolute structure	Flack (1983), 1755 Friedel pairs
Absolute structure parameter	0.14 (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···A	D—H	H···A	D···A	D—H···A
C3—H3B···O1	0.98	2.52	3.181 (8)	125.00
C10—H10B···N1	0.96	2.56	3.148 (7)	120.00
C11—H11A···N2	0.96	2.23	2.697 (7)	109.00
C11—H11C···Fⁱ	0.96	2.34	3.302 (8)	177.00

Symmetry code: (i) −x+2, −y+1, z+1/2.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals 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
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 6| June 2008| Page o1126

doi:10.1107/S1600536808013524

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

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