6-(2-Chloro-4-fluoro­benzyl­amino)purine

Trávníček, Z.; Marek, J.; Popa, I.

doi:10.1107/S1600536806009895

6-(2-Chloro-4-fluorobenzylamino)purine

In the title molecule, C₁₂H₉ClFN₅, all bond lengths and angles show normal values. The mean planes of the benzene ring and the purine ring system make a dihedral angle of 77.79 (5)°. Intermolecular N—H

N hydrogen bonds link the molecules into ribbons extending along the [1 $\overline{1}$ 0] direction. The crystal packing is further stablized by weak C—H

F and C—H

Cl interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806009895/cv2016sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806009895/cv2016Isup2.hkl Contains datablock I

CCDC reference: 605033

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Key indicators

Single-crystal X-ray study
T = 105 K
Mean (C-C)= 0.003 Å
R factor = 0.043
wR factor = 0.108
Data-to-parameter ratio = 11.9

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No errors found in this datablock

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PARST (Nardelli, 1995).

6-(2-Chloro-4-fluorobenzylamino)purine top

Crystal data top

C₁₂H₉ClFN₅	Z = 2
M_r = 277.69	F(000) = 284
Triclinic, P1	D_x = 1.573 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2544 (6) Å	Cell parameters from 3235 reflections
b = 7.3755 (7) Å	θ = 1.8–29.7°
c = 11.8649 (11) Å	µ = 0.33 mm⁻¹
α = 98.108 (8)°	T = 105 K
β = 101.603 (7)°	Prism, colourless
γ = 105.518 (8)°	0.30 × 0.30 × 0.25 mm
V = 586.28 (10) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer	1908 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Enhance (Oxford Diffraction) monochromator	θ_max = 25.0°, θ_min = 3.5°
Detector resolution: 16.3 pixels mm^-1	h = −8→8
rotation method, ω scans	k = −8→7
5335 measured reflections	l = −14→14
2063 independent reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.05P)² + 0.65P] where P = (F_o² + 2F_c²)/3
2063 reflections	(Δ/σ)_max = 0.002
173 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

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	Occ. (<1)
Cl	−0.25911 (8)	0.65716 (9)	0.62413 (5)	0.0348 (2)
F	0.1248 (2)	0.8330 (2)	0.32535 (12)	0.0413 (4)
N1	0.4265 (3)	0.4710 (2)	0.80081 (15)	0.0222 (4)
C2	0.5627 (3)	0.3804 (3)	0.81740 (18)	0.0238 (5)
H2	0.5292	0.2580	0.7671	0.029*
N3	0.7394 (2)	0.4360 (3)	0.89422 (15)	0.0211 (4)
H3	0.8226	0.3682	0.9001	0.025*	0.18 (4)
C4	0.7727 (3)	0.6110 (3)	0.96176 (18)	0.0196 (4)
C5	0.6467 (3)	0.7231 (3)	0.95572 (18)	0.0213 (4)
C6	0.4645 (3)	0.6469 (3)	0.87106 (18)	0.0211 (4)
N6	0.3306 (2)	0.7430 (2)	0.85901 (15)	0.0204 (4)
H6	0.3607	0.8580	0.9036	0.024*
N7	0.7273 (3)	0.8937 (2)	1.03853 (15)	0.0231 (4)
C8	0.8992 (3)	0.8800 (3)	1.09268 (19)	0.0238 (5)
H8	0.9899	0.9767	1.1558	0.029*
N9	0.9349 (3)	0.7146 (2)	1.04999 (15)	0.0207 (4)
H9	1.0415	0.6813	1.0745	0.025*	0.82 (4)
C9	0.1390 (3)	0.6653 (3)	0.77577 (18)	0.0202 (4)
H9A	0.0412	0.7104	0.8098	0.024*
H9B	0.0981	0.5233	0.7638	0.024*
C10	0.1353 (3)	0.7214 (3)	0.65746 (17)	0.0185 (4)
C11	−0.0396 (3)	0.7152 (3)	0.58047 (19)	0.0224 (5)
C12	−0.0470 (3)	0.7532 (3)	0.46859 (19)	0.0274 (5)
H12	−0.1677	0.7486	0.4173	0.033*
C13	0.1277 (4)	0.7977 (3)	0.43538 (19)	0.0283 (5)
C14	0.3045 (3)	0.8066 (3)	0.5066 (2)	0.0281 (5)
H14	0.4225	0.8371	0.4806	0.034*
C15	0.3062 (3)	0.7698 (3)	0.61787 (19)	0.0247 (5)
H15	0.4284	0.7779	0.6690	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0192 (3)	0.0444 (4)	0.0395 (4)	0.0122 (2)	0.0048 (2)	0.0035 (3)
F	0.0608 (10)	0.0380 (8)	0.0225 (7)	0.0113 (7)	0.0068 (7)	0.0110 (6)
N1	0.0209 (9)	0.0256 (9)	0.0193 (9)	0.0073 (7)	0.0039 (7)	0.0038 (7)
C2	0.0252 (11)	0.0254 (11)	0.0199 (10)	0.0065 (9)	0.0062 (9)	0.0036 (9)
N3	0.0181 (9)	0.0268 (9)	0.0195 (9)	0.0084 (7)	0.0036 (7)	0.0071 (7)
C4	0.0198 (10)	0.0252 (11)	0.0202 (10)	0.0114 (8)	0.0088 (8)	0.0109 (8)
C5	0.0234 (11)	0.0235 (10)	0.0196 (10)	0.0092 (9)	0.0066 (9)	0.0070 (8)
C6	0.0222 (10)	0.0260 (11)	0.0196 (10)	0.0098 (9)	0.0084 (8)	0.0099 (8)
N6	0.0193 (9)	0.0223 (9)	0.0199 (9)	0.0105 (7)	0.0012 (7)	0.0026 (7)
N7	0.0276 (10)	0.0208 (9)	0.0218 (9)	0.0089 (7)	0.0060 (8)	0.0049 (7)
C8	0.0248 (11)	0.0234 (11)	0.0245 (11)	0.0102 (9)	0.0043 (9)	0.0059 (9)
N9	0.0206 (9)	0.0225 (9)	0.0220 (9)	0.0113 (7)	0.0044 (7)	0.0062 (7)
C9	0.0175 (10)	0.0211 (10)	0.0230 (11)	0.0068 (8)	0.0060 (8)	0.0041 (8)
C10	0.0202 (10)	0.0136 (9)	0.0205 (10)	0.0062 (8)	0.0034 (8)	−0.0001 (8)
C11	0.0212 (11)	0.0181 (10)	0.0258 (11)	0.0077 (8)	0.0021 (9)	−0.0004 (8)
C12	0.0338 (13)	0.0199 (11)	0.0240 (11)	0.0116 (9)	−0.0048 (9)	0.0002 (9)
C13	0.0456 (14)	0.0175 (10)	0.0202 (11)	0.0080 (10)	0.0068 (10)	0.0043 (8)
C14	0.0306 (12)	0.0247 (11)	0.0266 (12)	0.0027 (9)	0.0099 (10)	0.0050 (9)
C15	0.0212 (11)	0.0261 (11)	0.0249 (11)	0.0059 (9)	0.0038 (9)	0.0047 (9)

Geometric parameters (Å, º) top

Cl—C11	1.737 (2)	C8—N9	1.364 (3)
F—C13	1.364 (3)	C8—H8	0.9500
N1—C2	1.332 (3)	N9—H9	0.8800
N1—C6	1.366 (3)	C9—C10	1.516 (3)
C2—N3	1.336 (3)	C9—H9A	0.9900
C2—H2	0.9500	C9—H9B	0.9900
N3—C4	1.353 (3)	C10—C15	1.389 (3)
N3—H3	0.8800	C10—C11	1.392 (3)
C4—N9	1.365 (3)	C11—C12	1.389 (3)
C4—C5	1.386 (3)	C12—C13	1.373 (3)
C5—N7	1.385 (3)	C12—H12	0.9500
C5—C6	1.407 (3)	C13—C14	1.366 (3)
C6—N6	1.344 (3)	C14—C15	1.383 (3)
N6—C9	1.449 (3)	C14—H14	0.9500
N6—H6	0.8800	C15—H15	0.9500
N7—C8	1.320 (3)

C2—N1—C6	118.16 (18)	C4—N9—H9	126.8
N1—C2—N3	129.6 (2)	N6—C9—C10	113.70 (17)
N1—C2—H2	115.2	N6—C9—H9A	108.8
N3—C2—H2	115.2	C10—C9—H9A	108.8
C2—N3—C4	110.65 (18)	N6—C9—H9B	108.8
C2—N3—H3	124.7	C10—C9—H9B	108.8
C4—N3—H3	124.7	H9A—C9—H9B	107.7
N3—C4—N9	128.00 (18)	C15—C10—C11	116.84 (19)
N3—C4—C5	126.74 (19)	C15—C10—C9	121.03 (18)
N9—C4—C5	105.26 (18)	C11—C10—C9	122.01 (18)
N7—C5—C4	111.41 (19)	C12—C11—C10	122.6 (2)
N7—C5—C6	131.81 (19)	C12—C11—Cl	117.92 (17)
C4—C5—C6	116.77 (19)	C10—C11—Cl	119.49 (17)
N6—C6—N1	120.48 (19)	C13—C12—C11	117.1 (2)
N6—C6—C5	121.48 (19)	C13—C12—H12	121.5
N1—C6—C5	118.03 (18)	C11—C12—H12	121.5
C6—N6—C9	122.76 (18)	F—C13—C14	118.2 (2)
C6—N6—H6	118.6	F—C13—C12	118.5 (2)
C9—N6—H6	118.6	C14—C13—C12	123.3 (2)
C8—N7—C5	102.89 (17)	C13—C14—C15	117.9 (2)
N7—C8—N9	114.00 (19)	C13—C14—H14	121.0
N7—C8—H8	123.0	C15—C14—H14	121.0
N9—C8—H8	123.0	C14—C15—C10	122.3 (2)
C8—N9—C4	106.43 (17)	C14—C15—H15	118.9
C8—N9—H9	126.8	C10—C15—H15	118.9

C6—N1—C2—N3	−0.7 (3)	N7—C8—N9—C4	−0.7 (2)
N1—C2—N3—C4	0.2 (3)	N3—C4—N9—C8	−179.3 (2)
C2—N3—C4—N9	179.58 (19)	C5—C4—N9—C8	0.4 (2)
C2—N3—C4—C5	−0.1 (3)	C6—N6—C9—C10	−92.3 (2)
N3—C4—C5—N7	179.61 (18)	N6—C9—C10—C15	25.0 (3)
N9—C4—C5—N7	−0.1 (2)	N6—C9—C10—C11	−159.18 (18)
N3—C4—C5—C6	0.4 (3)	C15—C10—C11—C12	0.6 (3)
N9—C4—C5—C6	−179.36 (18)	C9—C10—C11—C12	−175.38 (18)
C2—N1—C6—N6	−179.03 (19)	C15—C10—C11—Cl	−179.61 (15)
C2—N1—C6—C5	0.9 (3)	C9—C10—C11—Cl	4.4 (3)
N7—C5—C6—N6	0.1 (3)	C10—C11—C12—C13	0.2 (3)
C4—C5—C6—N6	179.16 (19)	Cl—C11—C12—C13	−179.61 (16)
N7—C5—C6—N1	−179.8 (2)	C11—C12—C13—F	179.07 (18)
C4—C5—C6—N1	−0.8 (3)	C11—C12—C13—C14	−0.3 (3)
N1—C6—N6—C9	2.3 (3)	F—C13—C14—C15	−179.73 (19)
C5—C6—N6—C9	−177.61 (18)	C12—C13—C14—C15	−0.4 (3)
C4—C5—N7—C8	−0.3 (2)	C13—C14—C15—C10	1.2 (3)
C6—C5—N7—C8	178.8 (2)	C11—C10—C15—C14	−1.3 (3)
C5—N7—C8—N9	0.6 (2)	C9—C10—C15—C14	174.72 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N9ⁱ	0.88	2.02	2.870 (2)	163
N6—H6···N7ⁱⁱ	0.88	2.16	2.953 (2)	149
N9—H9···N3ⁱ	0.88	2.00	2.870 (2)	170
C8—H8···Fⁱⁱⁱ	0.95	2.55	3.029 (3)	112
C15—H15···Cl^iv	0.95	2.77	3.459 (2)	131

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

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6-(2-Chloro-4-fluoro­benzyl­amino)purine

Supporting information

Key indicators

checkCIF/PLATON results

6-(2-Chloro-4-fluorobenzylamino)purine