N-[4-(4-Fluoro­phen­yl)-5-hy­droxy­methyl-6-isopropyl­pyrimidin-2-yl]-N-methyl­methane­sulfonamide

Xu, H.; Sun, H.; Luo, F.

doi:10.1107/S1600536811049051

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3432

https://doi.org/10.1107/S1600536811049051

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N-[4-(4-Fluorophenyl)-5-hydroxymethyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide

Hong Xu,^a Hong-shun Sun ^b ^* and Feng-mao Luo ^c

^aDepartment of Chemical Engineering, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China, ^bDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Geguan Road No. 265 Nanjing, Nanjing 210048, People's Republic of China, and ^cNanjing Xiansheng Dongyuan Pharmaceutic Company Limited, Xinglong Road No. 8 Nanjing, Nanjing 211800, People's Republic of China
^*Correspondence e-mail: njutshs@126.com

(Received 26 September 2011; accepted 17 November 2011; online 25 November 2011)

In the title compound, C₁₆H₂₀FN₃O₃S, the pyrimidine and benzene rings are oriented at a dihedral angle of 38.8 (3)°. An intramolecular C—H⋯O hydrogen bond occurs. The crystal structure is stabilized by O—H⋯N hydrogen bonds. In addition, C—H⋯O interactions are also present.

Related literature

For a related structure, see: He et al. (2008 ).

Experimental

Crystal data

C₁₆H₂₀FN₃O₃S
M_r = 353.41
Monoclinic, P 2₁ /c
a = 5.8080 (12) Å
b = 11.803 (2) Å
c = 25.867 (5) Å
β = 93.10 (3)°
V = 1770.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 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
3576 measured reflections
3234 independent reflections
2200 reflections with I > 2σ(I)
R_int = 0.034
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.168
S = 1.00
3234 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2ⁱ	0.82	2.10	2.896 (3)	165
C5—H5A⋯O1	0.93	2.53	3.309 (4)	141
C15—H15C⋯O3ⁱⁱ	0.96	2.39	3.350 (4)	176
C16—H16A⋯O3ⁱⁱⁱ	0.96	2.55	3.402 (4)	148
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) -x, -y+1, -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: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049051/pv2454sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049051/pv2454Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049051/pv2454Isup3.cml

checkCIF report

Comment top

The derivatives of pyrimidine are important chemical compound. We report here the crystal structure of the title compound.

In the title molecule (Fig. 1), the pyrimidine (N1/N2/C7—C10) and benzene (C1—C6) rings are inclined at a dihedral angle of 38.7 (3)°. The structure is stabilized by intermolecular hydrogen bonding of the type O—H···N. In addition, intramolecular C—H···N and C—H···O and intermolecular C—H···O hydrogen bonding interactions are also present in the crystal structure (Table 1). The crystal structure of a related compound has been reported recently (He et al., 2008).

Related literature top

For a related structure, see: He et al. (2008).

Experimental top

For the preparation of the title compound, sodium salt of N-methyl methane sulphonamide (106 g, 631.00 mmol) and 4-(4-fluorophenyl)-6-isopropyl- 2-methyl sulfonylpyrimidine-5-methanol (92 g, 284.0 mmol) were added to dimethylformamide (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; 90%). Crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.

Structure description top

The derivatives of pyrimidine are important chemical compound. We report here the crystal structure of the title compound.

For a related structure, see: He et al. (2008).

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing displacement ellipsoids at the 50% probability level.

N-[4-(4-Fluorophenyl)-5-hydroxymethyl-6-isopropylpyrimidin-2-yl]- N-methylmethanesulfonamide top

Crystal data top

C₁₆H₂₀FN₃O₃S	F(000) = 744
M_r = 353.41	D_x = 1.326 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 5.8080 (12) Å	θ = 9–13°
b = 11.803 (2) Å	µ = 0.21 mm⁻¹
c = 25.867 (5) Å	T = 293 K
β = 93.10 (3)°	Block, colorless
V = 1770.6 (6) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2200 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 25.4°, θ_min = 1.6°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
T_min = 0.939, T_max = 0.979	l = −31→31
3576 measured reflections	3 standard reflections every 200 reflections
3234 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.098P)²] where P = (F_o² + 2F_c²)/3
3234 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₆H₂₀FN₃O₃S	V = 1770.6 (6) Å³
M_r = 353.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.8080 (12) Å	µ = 0.21 mm⁻¹
b = 11.803 (2) Å	T = 293 K
c = 25.867 (5) Å	0.30 × 0.20 × 0.10 mm
β = 93.10 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2200 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.034
T_min = 0.939, T_max = 0.979	3 standard reflections every 200 reflections
3576 measured reflections	intensity decay: 1%
3234 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.00	Δρ_max = 0.27 e Å⁻³
3234 reflections	Δρ_min = −0.35 e Å⁻³
217 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
S	0.19836 (15)	0.47414 (7)	0.06975 (3)	0.0468 (3)
F	0.3816 (4)	0.31374 (19)	0.44364 (7)	0.0810 (7)
O1	−0.2240 (4)	0.06223 (19)	0.24443 (9)	0.0574 (7)
H1A	−0.2602	0.0043	0.2595	0.086*
N1	0.1043 (4)	0.2659 (2)	0.12672 (9)	0.0390 (6)
C1	0.4508 (6)	0.3093 (3)	0.30694 (13)	0.0491 (8)
H1C	0.5589	0.3309	0.2836	0.059*
O2	0.2945 (5)	0.58313 (19)	0.06090 (9)	0.0665 (7)
N2	0.2636 (4)	0.34440 (19)	0.20528 (9)	0.0358 (6)
C2	0.4998 (7)	0.3252 (3)	0.35873 (14)	0.0572 (9)
H2C	0.6402	0.3558	0.3708	0.069*
N3	0.3087 (5)	0.4355 (2)	0.12759 (9)	0.0454 (7)
O3	−0.0463 (4)	0.4631 (2)	0.06957 (9)	0.0610 (7)
C3	0.3365 (7)	0.2948 (3)	0.39237 (12)	0.0548 (9)
C4	0.1316 (7)	0.2479 (3)	0.37660 (13)	0.0550 (9)
H4A	0.0251	0.2278	0.4006	0.066*
C5	0.0833 (6)	0.2305 (3)	0.32381 (12)	0.0453 (8)
H5A	−0.0562	0.1979	0.3124	0.054*
C6	0.2421 (5)	0.2614 (2)	0.28818 (11)	0.0384 (7)
C7	0.1927 (5)	0.2532 (2)	0.23138 (11)	0.0362 (7)
C8	0.0778 (5)	0.1639 (2)	0.20606 (11)	0.0383 (7)
C9	0.0296 (5)	0.1763 (2)	0.15288 (11)	0.0374 (7)
C10	0.2204 (5)	0.3436 (2)	0.15435 (11)	0.0358 (7)
C11	0.0129 (6)	0.0571 (3)	0.23370 (13)	0.0461 (8)
H11A	0.0408	−0.0083	0.2122	0.055*
H11B	0.1062	0.0496	0.2658	0.055*
C12	−0.1153 (6)	0.0935 (3)	0.12057 (13)	0.0510 (9)
H12A	−0.1274	0.0234	0.1405	0.061*
C13	−0.3530 (8)	0.1421 (5)	0.1122 (2)	0.117 (2)
H13A	−0.4160	0.1570	0.1450	0.176*
H13B	−0.4498	0.0889	0.0932	0.176*
H13C	−0.3455	0.2114	0.0929	0.176*
C14	−0.0079 (9)	0.0648 (4)	0.07052 (16)	0.0964 (17)
H14A	0.1431	0.0337	0.0778	0.145*
H14B	0.0039	0.1322	0.0500	0.145*
H14C	−0.1023	0.0102	0.0518	0.145*
C15	0.5194 (6)	0.4925 (3)	0.14861 (13)	0.0599 (10)
H15A	0.5627	0.4619	0.1821	0.090*
H15B	0.4908	0.5722	0.1516	0.090*
H15C	0.6419	0.4803	0.1258	0.090*
C16	0.3091 (7)	0.3781 (3)	0.02622 (12)	0.0582 (10)
H16A	0.2511	0.3961	−0.0083	0.087*
H16B	0.2629	0.3027	0.0349	0.087*
H16C	0.4744	0.3828	0.0281	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0611 (6)	0.0414 (5)	0.0392 (5)	0.0019 (4)	0.0142 (4)	0.0066 (3)
F	0.124 (2)	0.0785 (16)	0.0398 (12)	0.0170 (14)	−0.0057 (12)	−0.0016 (10)
O1	0.0590 (16)	0.0441 (13)	0.0707 (16)	−0.0090 (11)	0.0171 (12)	0.0151 (11)
N1	0.0419 (14)	0.0378 (14)	0.0376 (14)	−0.0066 (12)	0.0051 (11)	−0.0017 (11)
C1	0.048 (2)	0.052 (2)	0.0471 (19)	0.0018 (16)	0.0007 (15)	0.0042 (15)
O2	0.099 (2)	0.0409 (14)	0.0616 (16)	−0.0055 (13)	0.0266 (14)	0.0134 (11)
N2	0.0414 (14)	0.0336 (13)	0.0332 (13)	−0.0017 (11)	0.0096 (10)	0.0011 (10)
C2	0.061 (2)	0.056 (2)	0.054 (2)	0.0067 (18)	−0.0092 (18)	0.0006 (17)
N3	0.0580 (17)	0.0442 (15)	0.0345 (14)	−0.0159 (13)	0.0089 (12)	0.0010 (11)
O3	0.0540 (15)	0.0709 (17)	0.0590 (15)	0.0089 (12)	0.0095 (11)	0.0162 (12)
C3	0.084 (3)	0.0451 (19)	0.0352 (18)	0.0163 (19)	−0.0012 (18)	0.0034 (15)
C4	0.077 (3)	0.047 (2)	0.0422 (19)	0.0133 (19)	0.0180 (18)	0.0092 (15)
C5	0.0510 (19)	0.0401 (17)	0.0455 (18)	0.0035 (15)	0.0077 (15)	0.0080 (14)
C6	0.0438 (17)	0.0320 (15)	0.0394 (17)	0.0104 (14)	0.0034 (13)	0.0044 (12)
C7	0.0348 (16)	0.0353 (16)	0.0392 (16)	0.0049 (13)	0.0079 (12)	0.0038 (13)
C8	0.0417 (17)	0.0310 (15)	0.0428 (17)	0.0009 (13)	0.0079 (13)	0.0027 (13)
C9	0.0343 (16)	0.0345 (16)	0.0442 (17)	−0.0026 (13)	0.0089 (13)	−0.0017 (13)
C10	0.0387 (17)	0.0346 (16)	0.0349 (16)	−0.0016 (13)	0.0104 (12)	0.0001 (12)
C11	0.050 (2)	0.0355 (17)	0.054 (2)	0.0001 (14)	0.0067 (15)	0.0064 (14)
C12	0.051 (2)	0.0440 (19)	0.058 (2)	−0.0140 (16)	0.0015 (16)	−0.0028 (15)
C13	0.055 (3)	0.106 (4)	0.186 (6)	0.000 (3)	−0.040 (3)	−0.042 (4)
C14	0.109 (4)	0.110 (4)	0.073 (3)	−0.052 (3)	0.026 (3)	−0.047 (3)
C15	0.065 (2)	0.062 (2)	0.054 (2)	−0.0297 (19)	0.0150 (17)	−0.0032 (17)
C16	0.080 (3)	0.058 (2)	0.0375 (18)	0.008 (2)	0.0176 (17)	0.0002 (16)

Geometric parameters (Å, º) top

S—O2	1.426 (2)	C6—C7	1.485 (4)
S—O3	1.427 (3)	C7—C8	1.391 (4)
S—N3	1.659 (3)	C8—C9	1.396 (4)
S—C16	1.745 (3)	C8—C11	1.507 (4)
F—C3	1.356 (4)	C9—C12	1.511 (4)
O1—C11	1.419 (4)	C11—H11A	0.9700
O1—H1A	0.8200	C11—H11B	0.9700
N1—C10	1.325 (4)	C12—C13	1.500 (6)
N1—C9	1.340 (4)	C12—C14	1.506 (5)
C1—C2	1.367 (4)	C12—H12A	0.9800
C1—C6	1.400 (4)	C13—H13A	0.9600
C1—H1C	0.9300	C13—H13B	0.9600
N2—C10	1.328 (3)	C13—H13C	0.9600
N2—C7	1.347 (4)	C14—H14A	0.9600
C2—C3	1.369 (5)	C14—H14B	0.9600
C2—H2C	0.9300	C14—H14C	0.9600
N3—C10	1.399 (4)	C15—H15A	0.9600
N3—C15	1.474 (4)	C15—H15B	0.9600
C3—C4	1.355 (5)	C15—H15C	0.9600
C4—C5	1.395 (4)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.388 (4)	C16—H16C	0.9600
C5—H5A	0.9300

O2—S—O3	118.72 (16)	N1—C10—N2	127.1 (3)
O2—S—N3	104.90 (14)	N1—C10—N3	117.4 (3)
O3—S—N3	108.28 (14)	N2—C10—N3	115.5 (2)
O2—S—C16	108.74 (16)	O1—C11—C8	109.1 (2)
O3—S—C16	109.90 (18)	O1—C11—H11A	109.9
N3—S—C16	105.41 (16)	C8—C11—H11A	109.9
C11—O1—H1A	109.5	O1—C11—H11B	109.9
C10—N1—C9	116.3 (2)	C8—C11—H11B	109.9
C2—C1—C6	121.7 (3)	H11A—C11—H11B	108.3
C2—C1—H1C	119.2	C13—C12—C14	112.5 (4)
C6—C1—H1C	119.2	C13—C12—C9	108.3 (3)
C10—N2—C7	116.5 (2)	C14—C12—C9	112.1 (3)
C1—C2—C3	118.2 (3)	C13—C12—H12A	107.9
C1—C2—H2C	120.9	C14—C12—H12A	107.9
C3—C2—H2C	120.9	C9—C12—H12A	107.9
C10—N3—C15	119.3 (3)	C12—C13—H13A	109.5
C10—N3—S	121.7 (2)	C12—C13—H13B	109.5
C15—N3—S	118.7 (2)	H13A—C13—H13B	109.5
C4—C3—F	118.8 (3)	C12—C13—H13C	109.5
C4—C3—C2	122.9 (3)	H13A—C13—H13C	109.5
F—C3—C2	118.3 (4)	H13B—C13—H13C	109.5
C3—C4—C5	118.8 (3)	C12—C14—H14A	109.5
C3—C4—H4A	120.6	C12—C14—H14B	109.5
C5—C4—H4A	120.6	H14A—C14—H14B	109.5
C6—C5—C4	120.4 (3)	C12—C14—H14C	109.5
C6—C5—H5A	119.8	H14A—C14—H14C	109.5
C4—C5—H5A	119.8	H14B—C14—H14C	109.5
C5—C6—C1	118.1 (3)	N3—C15—H15A	109.5
C5—C6—C7	122.7 (3)	N3—C15—H15B	109.5
C1—C6—C7	119.1 (3)	H15A—C15—H15B	109.5
N2—C7—C8	121.4 (3)	N3—C15—H15C	109.5
N2—C7—C6	113.3 (3)	H15A—C15—H15C	109.5
C8—C7—C6	125.3 (3)	H15B—C15—H15C	109.5
C7—C8—C9	116.8 (3)	S—C16—H16A	109.5
C7—C8—C11	122.4 (3)	S—C16—H16B	109.5
C9—C8—C11	120.8 (3)	H16A—C16—H16B	109.5
N1—C9—C8	121.8 (3)	S—C16—H16C	109.5
N1—C9—C12	114.6 (3)	H16A—C16—H16C	109.5
C8—C9—C12	123.6 (3)	H16B—C16—H16C	109.5

C6—C1—C2—C3	−1.2 (5)	C6—C7—C8—C9	174.4 (3)
O2—S—N3—C10	167.0 (2)	N2—C7—C8—C11	175.2 (3)
O3—S—N3—C10	39.2 (3)	C6—C7—C8—C11	−7.2 (4)
C16—S—N3—C10	−78.3 (3)	C10—N1—C9—C8	−1.9 (4)
O2—S—N3—C15	−19.4 (3)	C10—N1—C9—C12	176.2 (3)
O3—S—N3—C15	−147.1 (3)	C7—C8—C9—N1	4.6 (4)
C16—S—N3—C15	95.3 (3)	C11—C8—C9—N1	−173.8 (3)
C1—C2—C3—C4	1.3 (5)	C7—C8—C9—C12	−173.3 (3)
C1—C2—C3—F	−178.0 (3)	C11—C8—C9—C12	8.3 (4)
F—C3—C4—C5	178.8 (3)	C9—N1—C10—N2	−2.6 (4)
C2—C3—C4—C5	−0.5 (5)	C9—N1—C10—N3	177.3 (2)
C3—C4—C5—C6	−0.4 (5)	C7—N2—C10—N1	4.0 (4)
C4—C5—C6—C1	0.5 (4)	C7—N2—C10—N3	−175.9 (2)
C4—C5—C6—C7	−175.1 (3)	C15—N3—C10—N1	−151.1 (3)
C2—C1—C6—C5	0.3 (5)	S—N3—C10—N1	22.6 (4)
C2—C1—C6—C7	176.1 (3)	C15—N3—C10—N2	28.9 (4)
C10—N2—C7—C8	−0.8 (4)	S—N3—C10—N2	−157.5 (2)
C10—N2—C7—C6	−178.7 (2)	C7—C8—C11—O1	100.5 (3)
C5—C6—C7—N2	136.6 (3)	C9—C8—C11—O1	−81.2 (3)
C1—C6—C7—N2	−39.0 (4)	N1—C9—C12—C13	−77.6 (4)
C5—C6—C7—C8	−41.2 (4)	C8—C9—C12—C13	100.4 (4)
C1—C6—C7—C8	143.3 (3)	N1—C9—C12—C14	47.0 (4)
N2—C7—C8—C9	−3.1 (4)	C8—C9—C12—C14	−134.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2ⁱ	0.82	2.10	2.896 (3)	165
C5—H5A···O1	0.93	2.53	3.309 (4)	141
C15—H15A···N2	0.96	2.33	2.765 (4)	107
C15—H15C···O3ⁱⁱ	0.96	2.39	3.350 (4)	176
C16—H16A···O3ⁱⁱⁱ	0.96	2.55	3.402 (4)	148

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₀FN₃O₃S
M_r	353.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	5.8080 (12), 11.803 (2), 25.867 (5)
β (°)	93.10 (3)
V (Å³)	1770.6 (6)
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
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	3576, 3234, 2200
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.168, 1.00
No. of reflections	3234
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.35

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2ⁱ	0.8200	2.1000	2.896 (3)	165.00
C5—H5A···O1	0.9300	2.5300	3.309 (4)	141.00
C15—H15C···O3ⁱⁱ	0.9600	2.3900	3.350 (4)	176.00
C16—H16A···O3ⁱⁱⁱ	0.9600	2.5500	3.402 (4)	148.00

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x+1, y, z; (iii) −x, −y+1, −z.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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
He, W., Yang, D.-L., Cui, Y.-T., Xu, Y.-M. & Guo, C. (2008). Acta Cryst. E64, o1126. Web of Science CSD CrossRef IUCr Journals 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 67| Part 12| December 2011| Page o3432

https://doi.org/10.1107/S1600536811049051

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

N-[4-(4-Fluoro­phen­yl)-5-hy­dr­oxy­methyl-6-iso­propyl­pyrimidin-2-yl]-N-methyl­methane­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[4-(4-Fluorophenyl)-5-hydroxymethyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide