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Mol­ecules of the the title compound, C12H10BrN5, are connected by N—H...N hydrogen bonds into linear chains. In contrast to similar electroneutral 6-benzyl­amino­purine derivatives, which are usually protonated at the N9 atom, the purine skeleton is protonated at the N7 position.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035872/bi2055sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035872/bi2055Isup2.hkl
Contains datablock I

CCDC reference: 623993

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.029
  • wR factor = 0.071
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

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Alert level C PLAT318_ALERT_2_C Check Hybridisation of N6 in Main Residue . ? PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br1 .. 3.58 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 and DIAMOND.

6-(4-Bromobenzylamino)purine top
Crystal data top
C12H10BrN5F(000) = 1216
Mr = 304.16Dx = 1.734 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6098 reflections
a = 8.8944 (4) Åθ = 2.4–31.1°
b = 11.2015 (5) ŵ = 3.52 mm1
c = 23.6518 (9) ÅT = 110 K
β = 98.564 (3)°Prism, colourless
V = 2330.17 (17) Å30.30 × 0.30 × 0.25 mm
Z = 8
Data collection top
Oxford Xcalibur CCD area-detector
diffractometer
2061 independent reflections
Radiation source: fine-focus sealed tube1976 reflections with I > 2σ(I)
Enhance (Oxford Diffraction) monochromatorRint = 0.024
ω scansθmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1010
Tmin = 0.369, Tmax = 0.417k = 1310
6766 measured reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.19 w = 1/[σ2(Fo2) + (0.0233P)2 + 9.0814P]
where P = (Fo2 + 2Fc2)/3
2061 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
Br10.02994 (3)0.34771 (3)0.021544 (13)0.02131 (11)
N10.0243 (3)0.3896 (2)0.14949 (10)0.0143 (5)
C20.0069 (3)0.5042 (3)0.16376 (12)0.0153 (6)
H2A0.05800.56170.14310.018*
N30.1164 (3)0.5482 (2)0.20298 (10)0.0148 (5)
C40.2017 (3)0.4611 (2)0.23172 (12)0.0138 (6)
C50.1796 (3)0.3392 (2)0.22165 (12)0.0130 (6)
N60.0361 (3)0.1882 (2)0.16313 (10)0.0169 (5)
H6A0.09420.13240.18120.020*
C60.0627 (3)0.3028 (3)0.17795 (12)0.0140 (6)
N70.2894 (3)0.2831 (2)0.26043 (9)0.0143 (5)
H7A0.30490.20570.26440.017*
C80.3678 (3)0.3712 (2)0.29088 (12)0.0159 (6)
H8A0.44930.35630.32080.019*
C90.0866 (3)0.1532 (3)0.11787 (12)0.0160 (6)
H9A0.18430.15300.13320.019*
H9B0.09440.21210.08640.019*
N90.3208 (3)0.4801 (2)0.27536 (10)0.0158 (5)
C100.0577 (3)0.0308 (2)0.09506 (11)0.0135 (6)
C110.0822 (3)0.0026 (3)0.07770 (12)0.0172 (6)
H11A0.15970.06160.08050.021*
C120.1095 (3)0.1086 (3)0.05663 (12)0.0160 (6)
H12A0.20530.12690.04560.019*
C130.0052 (3)0.1935 (3)0.05177 (11)0.0143 (6)
C140.1456 (3)0.1690 (2)0.06776 (12)0.0154 (6)
H14A0.22360.22770.06390.018*
C150.1698 (3)0.0563 (3)0.08968 (12)0.0144 (6)
H15A0.26530.03870.10120.017*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02508 (18)0.01611 (17)0.02264 (18)0.00447 (12)0.00320 (12)0.00557 (12)
N10.0154 (12)0.0131 (12)0.0146 (12)0.0010 (9)0.0031 (9)0.0009 (10)
C20.0195 (15)0.0130 (14)0.0141 (14)0.0035 (11)0.0051 (11)0.0015 (11)
N30.0194 (13)0.0120 (12)0.0140 (12)0.0001 (10)0.0055 (10)0.0004 (9)
C40.0170 (14)0.0139 (14)0.0119 (13)0.0002 (11)0.0066 (11)0.0019 (11)
C50.0140 (14)0.0116 (14)0.0141 (14)0.0013 (11)0.0044 (11)0.0023 (11)
N60.0198 (13)0.0106 (12)0.0182 (13)0.0015 (10)0.0033 (10)0.0012 (10)
C60.0166 (14)0.0134 (14)0.0126 (13)0.0001 (11)0.0047 (11)0.0005 (11)
N70.0200 (13)0.0104 (12)0.0121 (12)0.0012 (10)0.0011 (9)0.0004 (9)
C80.0191 (15)0.0150 (15)0.0133 (13)0.0008 (12)0.0018 (11)0.0022 (11)
C90.0175 (15)0.0127 (14)0.0161 (14)0.0018 (11)0.0029 (11)0.0010 (11)
N90.0196 (13)0.0123 (12)0.0150 (12)0.0012 (10)0.0014 (9)0.0022 (10)
C100.0167 (14)0.0132 (14)0.0097 (13)0.0014 (11)0.0014 (10)0.0021 (11)
C110.0149 (14)0.0187 (15)0.0174 (14)0.0038 (12)0.0005 (11)0.0032 (12)
C120.0131 (14)0.0212 (15)0.0135 (13)0.0016 (12)0.0017 (11)0.0026 (12)
C130.0201 (15)0.0112 (13)0.0113 (13)0.0026 (11)0.0010 (11)0.0022 (11)
C140.0140 (14)0.0139 (14)0.0170 (14)0.0015 (11)0.0017 (11)0.0000 (11)
C150.0139 (14)0.0153 (14)0.0137 (13)0.0016 (11)0.0008 (11)0.0010 (11)
Geometric parameters (Å, º) top
Br1—C131.913 (3)C8—N91.323 (4)
N1—C21.345 (4)C8—H8A0.950
N1—C61.357 (4)C9—C101.510 (4)
C2—N31.336 (4)C9—H9A0.990
C2—H2A0.950C9—H9B0.990
N3—C41.355 (4)C10—C151.387 (4)
C4—N91.381 (4)C10—C111.403 (4)
C4—C51.396 (4)C11—C121.377 (4)
C5—N71.386 (4)C11—H11A0.950
C5—C61.413 (4)C12—C131.386 (4)
N6—C61.343 (4)C12—H12A0.950
N6—C91.464 (4)C13—C141.385 (4)
N6—H6A0.880C14—C151.394 (4)
N7—C81.353 (4)C14—H14A0.950
N7—H7A0.880C15—H15A0.950
C2—N1—C6118.5 (2)N6—C9—H9A109.5
N3—C2—N1128.9 (3)C10—C9—H9A109.5
N3—C2—H2A115.5N6—C9—H9B109.5
N1—C2—H2A115.5C10—C9—H9B109.5
C2—N3—C4112.3 (2)H9A—C9—H9B108.1
N3—C4—N9125.0 (3)C8—N9—C4103.9 (2)
N3—C4—C5124.4 (3)C15—C10—C11118.2 (3)
N9—C4—C5110.6 (2)C15—C10—C9120.9 (3)
N7—C5—C4105.3 (2)C11—C10—C9121.0 (3)
N7—C5—C6136.3 (3)C12—C11—C10121.4 (3)
C4—C5—C6118.4 (3)C12—C11—H11A119.3
C6—N6—C9122.0 (2)C10—C11—H11A119.3
C6—N6—H6A119.0C11—C12—C13118.9 (3)
C9—N6—H6A119.0C11—C12—H12A120.5
N6—C6—N1119.3 (3)C13—C12—H12A120.5
N6—C6—C5123.3 (3)C14—C13—C12121.6 (3)
N1—C6—C5117.4 (2)C14—C13—Br1119.0 (2)
C8—N7—C5106.1 (2)C12—C13—Br1119.4 (2)
C8—N7—H7A126.9C13—C14—C15118.4 (3)
C5—N7—H7A126.9C13—C14—H14A120.8
N9—C8—N7114.2 (3)C15—C14—H14A120.8
N9—C8—H8A122.9C10—C15—C14121.5 (3)
N7—C8—H8A122.9C10—C15—H15A119.2
N6—C9—C10110.9 (2)C14—C15—H15A119.2
C6—N1—C2—N31.0 (4)C5—N7—C8—N90.7 (3)
N1—C2—N3—C41.7 (4)C6—N6—C9—C10159.1 (3)
C2—N3—C4—N9178.7 (3)N7—C8—N9—C40.6 (3)
C2—N3—C4—C50.5 (4)N3—C4—N9—C8179.0 (3)
N3—C4—C5—N7179.4 (2)C5—C4—N9—C80.2 (3)
N9—C4—C5—N70.1 (3)N6—C9—C10—C15130.4 (3)
N3—C4—C5—C61.2 (4)N6—C9—C10—C1150.8 (3)
N9—C4—C5—C6179.5 (2)C15—C10—C11—C121.0 (4)
C9—N6—C6—N11.4 (4)C9—C10—C11—C12179.7 (3)
C9—N6—C6—C5179.6 (3)C10—C11—C12—C131.0 (4)
C2—N1—C6—N6178.1 (3)C11—C12—C13—C140.2 (4)
C2—N1—C6—C50.9 (4)C11—C12—C13—Br1179.1 (2)
N7—C5—C6—N62.1 (5)C12—C13—C14—C150.6 (4)
C4—C5—C6—N6177.0 (3)Br1—C13—C14—C15179.9 (2)
N7—C5—C6—N1179.0 (3)C11—C10—C15—C140.1 (4)
C4—C5—C6—N11.9 (4)C9—C10—C15—C14178.9 (2)
C4—C5—N7—C80.5 (3)C13—C14—C15—C100.7 (4)
C6—C5—N7—C8179.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6A···N9i0.882.072.935 (3)166
N7—H7A···N3i0.882.012.856 (3)161
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

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