(RS)-(2-Bromo-4-fluoro­anilino)[2-(4,6-dimethoxy­pyrimidin-2-yl­oxy)phen­yl]acetonitrile

Li, Y.

doi:10.1107/S1600536809033819

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2295-o2296

doi:10.1107/S1600536809033819

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(RS)-(2-Bromo-4-fluoroanilino)[2-(4,6-dimethoxypyrimidin-2-yloxy)phenyl]acetonitrile

Yuan-xiang Li ^a ^*

^aChemistry and Chemical Engineering Department, Huaihua University, Huaihua 418008, People's Republic of China
^*Correspondence e-mail: hhhhxylyx@yahoo.com.cn

(Received 14 July 2009; accepted 24 August 2009; online 29 August 2009)

In the title compound, C₂₀H₁₆BrFN₄O₃, the pyrimidine and 2-bromo-4-fluorophenyl rings are twisted away from the central benzene ring, making dihedral angles of 77.7 (1) and 85.5 (1), respectively. A pair of C—H⋯F interactions is involved in an R₂²(8) motif, linking the molecules into dimers. These ring motifs are situated about the crystallographic centres of symmetry. C—H⋯O hydrogen bonds link the dimers into chains running parallel to [1 $[\overline{1}]$ 1]. Additionally, a weak C—F⋯π-electron ring interaction was observed in the crystal packing [F⋯Cg = 3.459 (4) Å; Cg is the centroid of the pyrimidine ring]. There is also an intramolecular N—H⋯Br interaction in the structure.

Related literature

Pyrimidinylbenzoates are highly effective herbicides with acetohydroxyacid synthase (AHAS) as a target, see: Duggleby & Pang (2000 ). For related structures, see: Li & Huang (2007 ); Li & Wang (2007 ). For bond-length data, see: Allen et al. (1987 ). For graph-set motifs, see: Etter et al. (1990 ).

Experimental

Crystal data

C₂₀H₁₆BrFN₄O₃
M_r = 459.28
Triclinic, $[P \overline 1]$
a = 8.9131 (4) Å
b = 10.6646 (4) Å
c = 11.7804 (5) Å
α = 67.235 (1)°
β = 82.088 (1)°
γ = 81.277 (2)°
V = 1016.77 (7) Å³
Z = 2
Mo Kα radiation
μ = 2.06 mm⁻¹
T = 299 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.606, T_max = 0.662
10737 measured reflections
4588 independent reflections
2636 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.166
S = 1.05
4588 reflections
267 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯Br1	0.830 (18)	2.74 (3)	3.065 (2)	105 (3)
C13—H13⋯O3	0.98	2.41	2.763 (3)	101
C17—H17⋯F1ⁱ	0.93	2.61	3.541 (4)	175
C20—H20⋯O3ⁱⁱ	0.93	2.68	3.477 (4)	145
C13—H13⋯O3ⁱⁱ	0.98	2.53	3.433 (3)	153
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y, -z+2.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033819/fb2161sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033819/fb2161Isup2.hkl

checkCIF report

Comment top

Pyrimidine derivatives are rich in various biological properties. In particular, pyrimidinylbenzoates are highly effective herbicides with acetohydroxyacid synthase (AHAS) as a target (Duggleby & Pang, 2000). Here we report the crystal structure of one of such a pyrimidine derivative.

In the title molecule (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987) being in accordance with the corresponding values in similar compounds (Li & Huang, 2007; Li & Wang, 2007). The pyrimidine (N1//N2//C3—C6) and the benzene rings (C15—C20) are twisted away from the mid-benzene ring (C7—C12) with the dihedral angles equal to 77.7 (1) and 85.4 (1)°, respectively. The interplanar angle between the pyrimidine (N1//N2//C3—C6) and the benzene ring (C15—C20) is only 16.6 (1)°.

Pairs of C—H···F interactions form a graph-set R₂²(8) (Etter et al., 1990) about the crystallographic centres of symmetry, i. e. the molecules form dimers. C-H···O hydrogen bonds link these dimers into one-dimensional chains running parallel to the [111] direction (Fig. 2). Additionally, a weak C—F···π-electron ring interaction is present in the crystal structure (F···Cg = 3.459 (4) Å, C18···Cg = 3.779 (5) Å, C···F···Cg = 92.9 (3)°. (Cg is the centroid of the pyrimidine ring defined by the atoms N1//N2//C3—C6; symmetry code x-1, y, z)). Moreover, there is an intramolecular N-H···Br interaction in the structure (Tab. 1; Fig. 2)).

Related literature top

Pyrimidinylbenzoates are highly effective herbicides with acetohydroxyacid synthase (AHAS) as a target, see: Duggleby & Pang (2000). For related structures, see: Li & Huang (2007); Li & Wang (2007). For bond-length data, see: Allen et al. (1987). For graph-set motifs, see: Etter et al. (1990).

Experimental top

Solution of 2-(4,6-dimethoxypyrimidin-2-yloxy)benzaldehyde (0.26 g, 1 mmol) and 4-bromo-2-fluoroaniline (0.21 g, 1.1 mmol) in 10 ml of methanol was stirred at room temperature for 0.5 h. Then trimethylsilanecarbonitrile (TMSCN) (0.15 g, 1.5 mmol) was added and the reaction mixture was stirred for another 12 h. The resulting mixture was filtered off by suction and the filter cake was washed with little methanol. The crude product was dried under infrared lamp and the title compound was obtained as a white solid (the yield 0.22 g, 74%, melting point: 383–385 K). The product was recrystallized from ethanol at room temperature to give block colourless crystals with average size: 0.20 × 0.15 × 0.10 mm.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. The title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.

Fig. 2. Section of the title structure, showing the a chain of the molecules linked by weak C-H···F and C-H···O interactions represented by dashed lines (Tab. 1). The chain is parallel to [111]. Also the N-H···Br interaction is shown. For the sake of clarity, the H atoms not involved in the hydrogen-bonds pattern have been omitted. Color code: C, black; H, white; N, blue; O, red; F, yellow; Br, green.

(RS)-(2-Bromo-4-fluoroanilino)[2-(4,6-dimethoxypyrimidin-2- yloxy)phenyl]acetonitrile top

Crystal data top

C₂₀H₁₆BrFN₄O₃	Z = 2
M_r = 459.28	F(000) = 464
Triclinic, P1	D_x = 1.500 Mg m⁻³
Hall symbol: -P 1	Melting point = 383–385 K
a = 8.9131 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6646 (4) Å	Cell parameters from 2760 reflections
c = 11.7804 (5) Å	θ = 2.3–24.1°
α = 67.235 (1)°	µ = 2.06 mm⁻¹
β = 82.088 (1)°	T = 299 K
γ = 81.277 (2)°	Block, colourless
V = 1016.77 (7) Å³	0.25 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4588 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2636 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
0.3° wide ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.606, T_max = 0.662	k = −13→13
10737 measured reflections	l = −15→15

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)] = 0.055	Hydrogen site location: difference Fourier map
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0884P)² + 0.0427P] where P = (F_o² + 2F_c²)/3
4588 reflections	(Δ/σ)_max < 0.001
267 parameters	Δρ_max = 0.83 e Å⁻³
1 restraint	Δρ_min = −0.47 e Å⁻³
59 constraints

Crystal data top

C₂₀H₁₆BrFN₄O₃	γ = 81.277 (2)°
M_r = 459.28	V = 1016.77 (7) Å³
Triclinic, P1	Z = 2
a = 8.9131 (4) Å	Mo Kα radiation
b = 10.6646 (4) Å	µ = 2.06 mm⁻¹
c = 11.7804 (5) Å	T = 299 K
α = 67.235 (1)°	0.25 × 0.20 × 0.20 mm
β = 82.088 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4588 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2636 reflections with I > 2σ(I)
T_min = 0.606, T_max = 0.662	R_int = 0.027
10737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.83 e Å⁻³
4588 reflections	Δρ_min = −0.47 e Å⁻³
267 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Br1	0.87179 (6)	0.19137 (4)	0.47691 (3)	0.1134 (3)
C1	0.8782 (7)	0.4408 (4)	0.8262 (5)	0.1187 (16)
H1A	0.8212	0.3653	0.8427	0.178*
H1B	0.8092	0.5218	0.8175	0.178*
H1C	0.9392	0.4212	0.8935	0.178*
C2	1.3827 (9)	0.1531 (8)	0.4604 (6)	0.174 (3)
H2A	1.4643	0.1246	0.5134	0.261*
H2B	1.4241	0.1733	0.3764	0.261*
H2C	1.3183	0.0810	0.4843	0.261*
C3	1.0640 (5)	0.3549 (4)	0.7042 (4)	0.0895 (11)
C4	1.1396 (6)	0.3699 (5)	0.5916 (4)	0.1173 (15)
H4	1.1326	0.4534	0.5254	0.141*
C5	1.2246 (5)	0.2596 (5)	0.5801 (4)	0.1054 (14)
C6	1.1638 (4)	0.1373 (3)	0.7778 (3)	0.0650 (8)
C7	1.2094 (3)	−0.1058 (3)	0.8622 (2)	0.0581 (7)
C8	1.3569 (4)	−0.1646 (4)	0.8608 (3)	0.0783 (9)
H8	1.4359	−0.1196	0.8658	0.094*
C9	1.3867 (4)	−0.2903 (4)	0.8520 (4)	0.0888 (11)
H9	1.4867	−0.3307	0.8506	0.107*
C10	1.2715 (5)	−0.3569 (4)	0.8453 (3)	0.0848 (11)
H10	1.2933	−0.4422	0.8391	0.102*
C11	1.1221 (4)	−0.2986 (3)	0.8477 (3)	0.0672 (8)
H11	1.0439	−0.3444	0.8426	0.081*
C12	1.0890 (3)	−0.1719 (3)	0.8578 (2)	0.0523 (6)
C13	0.9288 (3)	−0.1037 (3)	0.8654 (2)	0.0537 (7)
H13	0.9238	−0.0567	0.9230	0.064*
C14	0.8165 (4)	−0.2064 (4)	0.9153 (3)	0.0695 (8)
C15	0.7744 (3)	0.1025 (3)	0.7335 (3)	0.0580 (7)
C16	0.7497 (4)	0.2024 (3)	0.6176 (3)	0.0721 (8)
C17	0.6375 (5)	0.3112 (4)	0.6020 (4)	0.0936 (12)
H17	0.6229	0.3771	0.5237	0.112*
C18	0.5498 (5)	0.3204 (4)	0.7017 (4)	0.0931 (12)
C19	0.5653 (4)	0.2244 (4)	0.8178 (4)	0.0841 (10)
H19	0.5017	0.2317	0.8851	0.101*
C20	0.6787 (4)	0.1154 (3)	0.8330 (3)	0.0689 (8)
H20	0.6908	0.0496	0.9117	0.083*
F1	0.4432 (4)	0.4297 (3)	0.6871 (3)	0.1400 (11)
N1	1.0762 (3)	0.2366 (3)	0.8016 (2)	0.0702 (7)
N2	1.2403 (3)	0.1355 (3)	0.6752 (3)	0.0813 (8)
N3	0.7278 (4)	−0.2815 (4)	0.9507 (4)	0.1020 (11)
N4	0.8911 (3)	−0.0024 (2)	0.7473 (2)	0.0667 (7)
H4A	0.949 (3)	−0.018 (3)	0.692 (3)	0.080*
O1	0.9737 (4)	0.4619 (3)	0.7162 (3)	0.1144 (10)
O2	1.2974 (6)	0.2699 (5)	0.4710 (3)	0.1620 (17)
O3	1.1745 (2)	0.0177 (2)	0.88013 (18)	0.0660 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1488 (5)	0.1099 (4)	0.0510 (3)	0.0276 (3)	−0.0032 (2)	−0.0139 (2)
C1	0.169 (5)	0.078 (3)	0.107 (4)	−0.005 (3)	−0.004 (3)	−0.037 (3)
C2	0.200 (7)	0.172 (6)	0.102 (4)	−0.011 (5)	0.069 (5)	−0.030 (4)
C3	0.111 (3)	0.070 (2)	0.075 (2)	−0.019 (2)	−0.012 (2)	−0.0079 (18)
C4	0.142 (4)	0.082 (3)	0.087 (3)	−0.011 (3)	−0.001 (3)	0.010 (2)
C5	0.107 (3)	0.117 (3)	0.061 (2)	−0.026 (3)	0.021 (2)	−0.004 (2)
C6	0.071 (2)	0.0700 (19)	0.0497 (16)	−0.0244 (16)	−0.0043 (14)	−0.0116 (14)
C7	0.0611 (19)	0.0630 (17)	0.0426 (14)	−0.0014 (14)	−0.0020 (12)	−0.0140 (12)
C8	0.059 (2)	0.101 (3)	0.069 (2)	0.0008 (18)	−0.0023 (15)	−0.0300 (19)
C9	0.065 (2)	0.107 (3)	0.077 (2)	0.026 (2)	−0.0007 (17)	−0.030 (2)
C10	0.102 (3)	0.0647 (19)	0.075 (2)	0.022 (2)	0.003 (2)	−0.0269 (17)
C11	0.077 (2)	0.0568 (16)	0.0649 (19)	0.0034 (15)	0.0013 (15)	−0.0256 (14)
C12	0.0566 (16)	0.0501 (14)	0.0428 (13)	0.0045 (12)	−0.0038 (11)	−0.0132 (11)
C13	0.0570 (16)	0.0505 (14)	0.0485 (14)	0.0048 (12)	−0.0048 (12)	−0.0170 (12)
C14	0.061 (2)	0.0687 (19)	0.072 (2)	0.0060 (17)	−0.0083 (16)	−0.0233 (16)
C15	0.0625 (17)	0.0557 (15)	0.0544 (16)	0.0062 (13)	−0.0135 (13)	−0.0209 (13)
C16	0.087 (2)	0.0671 (18)	0.0529 (17)	0.0105 (16)	−0.0157 (15)	−0.0164 (14)
C17	0.117 (3)	0.072 (2)	0.075 (2)	0.033 (2)	−0.036 (2)	−0.0161 (18)
C18	0.100 (3)	0.080 (2)	0.095 (3)	0.043 (2)	−0.034 (2)	−0.038 (2)
C19	0.076 (2)	0.094 (2)	0.080 (2)	0.0272 (18)	−0.0168 (18)	−0.041 (2)
C20	0.0686 (19)	0.0682 (18)	0.0601 (18)	0.0153 (15)	−0.0097 (14)	−0.0203 (15)
F1	0.155 (2)	0.1206 (19)	0.129 (2)	0.0875 (17)	−0.0487 (17)	−0.0542 (16)
N1	0.0928 (19)	0.0533 (14)	0.0608 (15)	−0.0158 (14)	−0.0069 (13)	−0.0143 (12)
N2	0.0848 (19)	0.0860 (19)	0.0580 (16)	−0.0188 (15)	0.0059 (14)	−0.0110 (14)
N3	0.070 (2)	0.094 (2)	0.132 (3)	−0.0117 (18)	−0.0006 (19)	−0.033 (2)
N4	0.0713 (16)	0.0654 (14)	0.0482 (14)	0.0183 (12)	−0.0040 (11)	−0.0146 (11)
O1	0.158 (3)	0.0604 (15)	0.103 (2)	−0.0037 (16)	−0.018 (2)	−0.0078 (14)
O2	0.190 (4)	0.146 (3)	0.082 (2)	−0.004 (3)	0.054 (2)	0.004 (2)
O3	0.0870 (14)	0.0585 (12)	0.0492 (11)	−0.0112 (10)	−0.0040 (10)	−0.0159 (9)

Geometric parameters (Å, º) top

Br1—C16	1.887 (3)	C9—C10	1.361 (6)
C1—O1	1.409 (5)	C9—H9	0.9300
C1—H1A	0.9600	C10—C11	1.383 (5)
C1—H1B	0.9600	C10—H10	0.9300
C1—H1C	0.9600	C11—C12	1.386 (4)
C2—O2	1.397 (8)	C11—H11	0.9300
C2—H2A	0.9600	C12—C13	1.508 (4)
C2—H2B	0.9600	C13—N4	1.439 (3)
C2—H2C	0.9600	C13—C14	1.491 (5)
C3—O1	1.335 (5)	C13—H13	0.9800
C3—N1	1.339 (4)	C14—N3	1.132 (4)
C3—C4	1.364 (6)	C15—N4	1.383 (4)
C4—C5	1.342 (7)	C15—C16	1.390 (4)
C4—H4	0.9300	C15—C20	1.391 (4)
C5—O2	1.330 (5)	C16—C17	1.383 (5)
C5—N2	1.365 (5)	C17—C18	1.347 (5)
C6—N2	1.310 (4)	C17—H17	0.9300
C6—N1	1.314 (4)	C18—F1	1.358 (4)
C6—O3	1.376 (3)	C18—C19	1.365 (5)
C7—C8	1.369 (4)	C19—C20	1.392 (5)
C7—C12	1.387 (4)	C19—H19	0.9300
C7—O3	1.396 (3)	C20—H20	0.9300
C8—C9	1.367 (5)	N4—H4A	0.830 (18)
C8—H8	0.9300

O1—C1—H1A	109.5	C12—C11—H11	120.0
O1—C1—H1B	109.5	C11—C12—C7	118.1 (3)
H1A—C1—H1B	109.5	C11—C12—C13	123.2 (3)
O1—C1—H1C	109.5	C7—C12—C13	118.8 (2)
H1A—C1—H1C	109.5	N4—C13—C14	111.1 (2)
H1B—C1—H1C	109.5	N4—C13—C12	111.2 (2)
O2—C2—H2A	109.5	C14—C13—C12	111.2 (2)
O2—C2—H2B	109.5	N4—C13—H13	107.7
H2A—C2—H2B	109.5	C14—C13—H13	107.7
O2—C2—H2C	109.5	C12—C13—H13	107.7
H2A—C2—H2C	109.5	N3—C14—C13	177.8 (4)
H2B—C2—H2C	109.5	N4—C15—C16	120.6 (3)
O1—C3—N1	119.5 (4)	N4—C15—C20	122.5 (3)
O1—C3—C4	118.4 (4)	C16—C15—C20	116.8 (3)
N1—C3—C4	122.1 (4)	C17—C16—C15	121.7 (3)
C5—C4—C3	117.5 (4)	C17—C16—Br1	118.5 (3)
C5—C4—H4	121.3	C15—C16—Br1	119.8 (2)
C3—C4—H4	121.3	C18—C17—C16	119.1 (3)
O2—C5—C4	119.0 (4)	C18—C17—H17	120.5
O2—C5—N2	117.6 (5)	C16—C17—H17	120.5
C4—C5—N2	123.4 (4)	C17—C18—F1	119.1 (4)
N2—C6—N1	130.7 (3)	C17—C18—C19	122.3 (3)
N2—C6—O3	116.9 (3)	F1—C18—C19	118.5 (4)
N1—C6—O3	112.5 (3)	C18—C19—C20	118.3 (3)
C8—C7—C12	121.7 (3)	C18—C19—H19	120.9
C8—C7—O3	120.4 (3)	C20—C19—H19	120.9
C12—C7—O3	117.7 (2)	C15—C20—C19	121.7 (3)
C9—C8—C7	119.2 (3)	C15—C20—H20	119.2
C9—C8—H8	120.4	C19—C20—H20	119.2
C7—C8—H8	120.4	C6—N1—C3	114.1 (3)
C10—C9—C8	120.7 (3)	C6—N2—C5	112.2 (3)
C10—C9—H9	119.7	C15—N4—C13	123.3 (2)
C8—C9—H9	119.7	C15—N4—H4A	127 (3)
C9—C10—C11	120.5 (3)	C13—N4—H4A	110 (3)
C9—C10—H10	119.8	C3—O1—C1	118.3 (3)
C11—C10—H10	119.8	C5—O2—C2	118.1 (4)
C10—C11—C12	119.9 (3)	C6—O3—C7	118.4 (2)
C10—C11—H11	120.0

O1—C3—C4—C5	−177.2 (5)	C16—C17—C18—C19	−1.4 (7)
N1—C3—C4—C5	2.0 (7)	C17—C18—C19—C20	1.7 (7)
C3—C4—C5—O2	178.7 (4)	F1—C18—C19—C20	−177.5 (4)
C3—C4—C5—N2	−1.0 (8)	N4—C15—C20—C19	177.7 (3)
C12—C7—C8—C9	1.6 (5)	C16—C15—C20—C19	−1.1 (5)
O3—C7—C8—C9	175.3 (3)	C18—C19—C20—C15	−0.3 (6)
C7—C8—C9—C10	−0.3 (5)	N2—C6—N1—C3	0.0 (5)
C8—C9—C10—C11	−0.2 (6)	O3—C6—N1—C3	179.6 (3)
C9—C10—C11—C12	−0.4 (5)	O1—C3—N1—C6	177.7 (3)
C10—C11—C12—C7	1.6 (4)	C4—C3—N1—C6	−1.4 (6)
C10—C11—C12—C13	−177.9 (3)	N1—C6—N2—C5	0.9 (5)
C8—C7—C12—C11	−2.2 (4)	O3—C6—N2—C5	−178.8 (3)
O3—C7—C12—C11	−176.1 (2)	O2—C5—N2—C6	−180.0 (4)
C8—C7—C12—C13	177.3 (3)	C4—C5—N2—C6	−0.3 (7)
O3—C7—C12—C13	3.4 (4)	C16—C15—N4—C13	175.8 (3)
C11—C12—C13—N4	−99.4 (3)	C20—C15—N4—C13	−2.9 (5)
C7—C12—C13—N4	81.2 (3)	C14—C13—N4—C15	75.8 (4)
C11—C12—C13—C14	25.0 (4)	C12—C13—N4—C15	−159.8 (3)
C7—C12—C13—C14	−154.5 (3)	N1—C3—O1—C1	−8.6 (6)
N4—C15—C16—C17	−177.5 (3)	C4—C3—O1—C1	170.5 (4)
C20—C15—C16—C17	1.3 (5)	C4—C5—O2—C2	−178.7 (6)
N4—C15—C16—Br1	2.3 (4)	N2—C5—O2—C2	1.0 (9)
C20—C15—C16—Br1	−178.9 (2)	N2—C6—O3—C7	−25.3 (4)
C15—C16—C17—C18	−0.1 (6)	N1—C6—O3—C7	155.0 (3)
Br1—C16—C17—C18	−179.9 (3)	C8—C7—O3—C6	94.9 (3)
C16—C17—C18—F1	177.8 (4)	C12—C7—O3—C6	−91.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···Br1	0.83 (2)	2.74 (3)	3.065 (2)	105 (3)
C13—H13···O3	0.98	2.41	2.763 (3)	101
C17—H17···F1ⁱ	0.93	2.61	3.541 (4)	175
C20—H20···O3ⁱⁱ	0.93	2.68	3.477 (4)	145
C13—H13···O3ⁱⁱ	0.98	2.53	3.433 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆BrFN₄O₃
M_r	459.28
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	8.9131 (4), 10.6646 (4), 11.7804 (5)
α, β, γ (°)	67.235 (1), 82.088 (1), 81.277 (2)
V (Å³)	1016.77 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.06
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.606, 0.662
No. of measured, independent and observed [I > 2σ(I)] reflections	10737, 4588, 2636
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.166, 1.05
No. of reflections	4588
No. of parameters	267
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.47

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···Br1	0.830 (18)	2.74 (3)	3.065 (2)	105 (3)
C13—H13···O3	0.98	2.41	2.763 (3)	100.8
C17—H17···F1ⁱ	0.93	2.61	3.541 (4)	174.5
C20—H20···O3ⁱⁱ	0.93	2.68	3.477 (4)	144.8
C13—H13···O3ⁱⁱ	0.98	2.53	3.433 (3)	153.3

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

Acknowledgements

The author acknowledges financial support by the Opening Fund of the Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education of China), Hunan Normal University (No. KLCBTCMR2008–05), the Hunan Province Natural Science Foundation of China (No.09 J J6023) and the Scientific Research Foundation of Huaihua University.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Duggleby, R. G. & Pang, S. S. (2000). J. Biochem. Mol. Biol. 33, 1–36. CAS Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, Y. & Huang, G. (2007). Acta Cryst. E63, o4667. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, Y.-X. & Wang, Y.-Z. (2007). Acta Cryst. E63, o873–o874. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 9| September 2009| Pages o2295-o2296

doi:10.1107/S1600536809033819

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

(RS)-(2-Bromo-4-fluoro­anilino)[2-(4,6-di­meth­oxy­pyrimidin-2-yl­­oxy)phen­yl]aceto­nitrile

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(RS)-(2-Bromo-4-fluoroanilino)[2-(4,6-dimethoxypyrimidin-2-yloxy)phenyl]acetonitrile