6-(3-Bromo­benzyl­amino)purin-3-ium chloride

In the title compound, C₁₂H₁₁BrN₅⁺·Cl⁻, the cation exists as the N3-protonated N7 tautomer. The crystal structure is stabilized by N—H...Cl hydrogen bonds, which connect cations and anions into linear chains along the [010] direction. There are also some additional π–π stacking inter­actions and weak inter­atomic contacts of the types C...Cl and C...Br.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C)= 0.005 Å
• R factor = 0.043
• wR factor = 0.106
• Data-to-parameter ratio = 13.5

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Computing details

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, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 and DIAMOND (Brandenburg, 2006).

6-(3-Bromobenzylamino)purin-3-ium chloride

Crystal data

C12H11BrN5^+·Cl^−	F(000) = 680
Mr = 340.62	Dx = 1.719 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2295 reflections
a = 18.823 (2) Å	θ = 3.2–28.8°
b = 8.8276 (11) Å	µ = 3.32 mm^−1
c = 7.9658 (11) Å	T = 100 K
β = 96.244 (10)°	Prism, colourless
V = 1315.8 (3) Å^3	0.35 × 0.25 × 0.20 mm
Z = 4

Data collection

Oxford Xcalibur2 diffractometer	2316 independent reflections
Radiation source: fine-focus sealed tube	2100 reflections with I > 2σ(I)
Enhance (Oxford Diffraction) monochromator	Rint = 0.058
Detector resolution: 16.3 pixels mm^-1	θmax = 25.0°, θmin = 3.5°
rotation method, ω scans	h = −22→22
Absorption correction: empirical (using intensity measurements) (Blessing, 1995)	k = −10→10
Tmin = 0.360, Tmax = 0.515	l = −6→9
6666 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0587P)^2 + 1.865P] where P = (Fo^2 + 2Fc^2)/3
2316 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.90 e Å^−3
0 restraints	Δρmin = −0.67 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.124482 (19)	0.37458 (5)	0.03153 (5)	0.03533 (17)
N1	0.29147 (14)	0.8093 (3)	0.5937 (3)	0.0163 (5)
Cl1	0.36705 (4)	0.29997 (8)	0.36066 (9)	0.0185 (2)
C2	0.31436 (17)	0.9452 (4)	0.5629 (4)	0.0169 (6)
H2A	0.2869	1.0284	0.5955	0.020*
N3	0.37315 (13)	0.9770 (3)	0.4892 (3)	0.0168 (6)
H3A	0.3867	1.0711	0.4752	0.020*
C4	0.41108 (17)	0.8590 (3)	0.4369 (4)	0.0152 (6)
C5	0.38913 (16)	0.7129 (3)	0.4637 (4)	0.0136 (6)
N6	0.30568 (14)	0.5500 (3)	0.5842 (3)	0.0167 (5)
H6A	0.3329	0.4713	0.5689	0.020*
C6	0.32843 (16)	0.6869 (3)	0.5467 (4)	0.0146 (6)
N7	0.43783 (14)	0.6233 (3)	0.3938 (3)	0.0151 (6)
H7A	0.4386	0.5237	0.3908	0.018*
C8	0.48413 (17)	0.7183 (4)	0.3308 (4)	0.0179 (6)
H8A	0.5232	0.6846	0.2746	0.022*
N9	0.47003 (15)	0.8637 (3)	0.3547 (3)	0.0171 (6)
C9	0.23722 (17)	0.5254 (4)	0.6497 (4)	0.0206 (7)
H9A	0.2315	0.6007	0.7393	0.025*
H9B	0.2371	0.4234	0.7013	0.025*
C10	0.17512 (17)	0.5381 (3)	0.5154 (4)	0.0176 (6)
C11	0.17802 (17)	0.4658 (4)	0.3601 (4)	0.0194 (7)
H11A	0.2195	0.4118	0.3372	0.023*
C12	0.11931 (19)	0.4747 (4)	0.2411 (4)	0.0237 (7)
C13	0.05811 (18)	0.5522 (4)	0.2679 (5)	0.0281 (8)
H13A	0.0183	0.5559	0.1837	0.034*
C14	0.0564 (2)	0.6243 (4)	0.4209 (5)	0.0336 (9)
H14A	0.0149	0.6789	0.4428	0.040*
C15	0.11461 (19)	0.6177 (4)	0.5431 (4)	0.0249 (8)
H15A	0.1127	0.6688	0.6475	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0239 (2)	0.0528 (3)	0.0279 (2)	−0.00378 (16)	−0.00354 (16)	−0.01291 (16)
N1	0.0172 (13)	0.0159 (13)	0.0148 (13)	0.0013 (11)	−0.0029 (10)	−0.0028 (10)
Cl1	0.0249 (4)	0.0110 (3)	0.0199 (4)	0.0019 (3)	0.0031 (3)	0.0019 (3)
C2	0.0193 (16)	0.0167 (15)	0.0137 (14)	0.0035 (13)	−0.0019 (12)	−0.0022 (12)
N3	0.0226 (14)	0.0102 (12)	0.0165 (13)	−0.0001 (10)	−0.0026 (11)	−0.0013 (10)
C4	0.0176 (16)	0.0144 (15)	0.0120 (14)	0.0000 (12)	−0.0059 (12)	0.0003 (11)
C5	0.0146 (15)	0.0123 (14)	0.0126 (15)	0.0004 (12)	−0.0044 (11)	−0.0006 (11)
N6	0.0188 (13)	0.0136 (12)	0.0174 (13)	−0.0017 (11)	0.0004 (10)	0.0006 (10)
C6	0.0187 (16)	0.0150 (14)	0.0090 (14)	−0.0004 (13)	−0.0042 (11)	−0.0011 (11)
N7	0.0176 (14)	0.0116 (12)	0.0155 (13)	0.0008 (10)	−0.0013 (10)	0.0000 (9)
C8	0.0155 (15)	0.0196 (15)	0.0178 (15)	−0.0009 (13)	−0.0022 (12)	−0.0011 (12)
N9	0.0182 (14)	0.0150 (13)	0.0173 (13)	−0.0019 (10)	−0.0017 (11)	−0.0008 (10)
C9	0.0244 (17)	0.0196 (16)	0.0181 (16)	−0.0047 (14)	0.0037 (13)	0.0002 (13)
C10	0.0178 (16)	0.0153 (14)	0.0207 (16)	−0.0045 (13)	0.0064 (12)	0.0028 (12)
C11	0.0153 (16)	0.0182 (15)	0.0252 (17)	−0.0007 (13)	0.0046 (13)	0.0011 (13)
C12	0.0234 (17)	0.0216 (16)	0.0254 (17)	−0.0034 (14)	0.0000 (13)	−0.0008 (14)
C13	0.0173 (17)	0.0321 (19)	0.0340 (19)	0.0006 (15)	−0.0011 (14)	0.0055 (16)
C14	0.023 (2)	0.032 (2)	0.047 (2)	0.0087 (15)	0.0086 (17)	0.0001 (17)
C15	0.0253 (19)	0.0218 (17)	0.0286 (19)	0.0016 (14)	0.0076 (15)	−0.0048 (13)

Geometric parameters (Å, º)

Br1—C12	1.901 (3)	C8—N9	1.329 (4)
N1—C2	1.307 (4)	C8—H8A	0.9500
N1—C6	1.360 (4)	C9—C10	1.501 (4)
C2—N3	1.337 (4)	C9—H9A	0.9900
C2—H2A	0.9500	C9—H9B	0.9900
N3—C4	1.354 (4)	C10—C15	1.376 (5)
N3—H3A	0.8800	C10—C11	1.398 (5)
C4—N9	1.349 (4)	C11—C12	1.378 (5)
C4—C5	1.377 (4)	C11—H11A	0.9500
C5—N7	1.374 (4)	C12—C13	1.376 (5)
C5—C6	1.400 (4)	C13—C14	1.378 (6)
N6—C6	1.327 (4)	C13—H13A	0.9500
N6—C9	1.458 (4)	C14—C15	1.386 (5)
N6—H6A	0.8800	C14—H14A	0.9500
N7—C8	1.345 (4)	C15—H15A	0.9500
N7—H7A	0.8800
C2—N1—C6	119.3 (3)	C8—N9—C4	103.1 (3)
N1—C2—N3	125.5 (3)	N6—C9—C10	112.6 (2)
N1—C2—H2A	117.3	N6—C9—H9A	109.1
N3—C2—H2A	117.3	C10—C9—H9A	109.1
C2—N3—C4	117.6 (3)	N6—C9—H9B	109.1
C2—N3—H3A	121.2	C10—C9—H9B	109.1
C4—N3—H3A	121.2	H9A—C9—H9B	107.8
N3—C4—N9	127.9 (3)	C15—C10—C11	119.2 (3)
N3—C4—C5	119.7 (3)	C15—C10—C9	121.2 (3)
N9—C4—C5	112.4 (3)	C11—C10—C9	119.6 (3)
N7—C5—C4	104.6 (3)	C12—C11—C10	118.5 (3)
N7—C5—C6	135.4 (3)	C12—C11—H11A	120.7
C4—C5—C6	120.0 (3)	C10—C11—H11A	120.7
C6—N6—C9	122.4 (3)	C11—C12—C13	122.9 (3)
C6—N6—H6A	118.8	C11—C12—Br1	117.7 (3)
C9—N6—H6A	118.8	C13—C12—Br1	119.4 (3)
N6—C6—N1	118.3 (3)	C14—C13—C12	117.9 (3)
N6—C6—C5	123.7 (3)	C14—C13—H13A	121.1
N1—C6—C5	117.9 (3)	C12—C13—H13A	121.1
C8—N7—C5	106.3 (2)	C13—C14—C15	120.6 (3)
C8—N7—H7A	126.9	C13—C14—H14A	119.7
C5—N7—H7A	126.9	C15—C14—H14A	119.7
N9—C8—N7	113.7 (3)	C10—C15—C14	120.9 (3)
N9—C8—H8A	123.2	C10—C15—H15A	119.5
N7—C8—H8A	123.2	C14—C15—H15A	119.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Cl1^i	0.88	2.23	3.028 (3)	150
N6—H6A···Cl1	0.88	2.38	3.134 (3)	143
N7—H7A···Cl1	0.88	2.39	3.149 (3)	145

Symmetry code: (i) x, y+1, z.