Molecules of the the title compound, C
12H
10BrN
5, 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
CCDC reference: 623993
Key indicators
- Single-crystal X-ray study
- T = 110 K
- Mean (C-C) = 0.004 Å
- R factor = 0.029
- wR factor = 0.071
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
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
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
C12H10BrN5 | F(000) = 1216 |
Mr = 304.16 | Dx = 1.734 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6098 reflections |
a = 8.8944 (4) Å | θ = 2.4–31.1° |
b = 11.2015 (5) Å | µ = 3.52 mm−1 |
c = 23.6518 (9) Å | T = 110 K |
β = 98.564 (3)° | Prism, colourless |
V = 2330.17 (17) Å3 | 0.30 × 0.30 × 0.25 mm |
Z = 8 | |
Data collection top
Oxford Xcalibur CCD area-detector diffractometer | 2061 independent reflections |
Radiation source: fine-focus sealed tube | 1976 reflections with I > 2σ(I) |
Enhance (Oxford Diffraction) monochromator | Rint = 0.024 |
ω scans | θmax = 25.0°, θmin = 2.9° |
Absorption correction: multi-scan (Blessing, 1995) | h = −10→10 |
Tmin = 0.369, Tmax = 0.417 | k = −13→10 |
6766 measured reflections | l = −28→28 |
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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | H-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 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.27 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 | Uiso*/Ueq | |
Br1 | 0.02994 (3) | 0.34771 (3) | 0.021544 (13) | 0.02131 (11) | |
N1 | −0.0243 (3) | −0.3896 (2) | 0.14949 (10) | 0.0143 (5) | |
C2 | 0.0069 (3) | −0.5042 (3) | 0.16376 (12) | 0.0153 (6) | |
H2A | −0.0580 | −0.5617 | 0.1431 | 0.018* | |
N3 | 0.1164 (3) | −0.5482 (2) | 0.20298 (10) | 0.0148 (5) | |
C4 | 0.2017 (3) | −0.4611 (2) | 0.23172 (12) | 0.0138 (6) | |
C5 | 0.1796 (3) | −0.3392 (2) | 0.22165 (12) | 0.0130 (6) | |
N6 | 0.0361 (3) | −0.1882 (2) | 0.16313 (10) | 0.0169 (5) | |
H6A | 0.0942 | −0.1324 | 0.1812 | 0.020* | |
C6 | 0.0627 (3) | −0.3028 (3) | 0.17795 (12) | 0.0140 (6) | |
N7 | 0.2894 (3) | −0.2831 (2) | 0.26043 (9) | 0.0143 (5) | |
H7A | 0.3049 | −0.2057 | 0.2644 | 0.017* | |
C8 | 0.3678 (3) | −0.3712 (2) | 0.29088 (12) | 0.0159 (6) | |
H8A | 0.4493 | −0.3563 | 0.3208 | 0.019* | |
C9 | −0.0866 (3) | −0.1532 (3) | 0.11787 (12) | 0.0160 (6) | |
H9A | −0.1843 | −0.1530 | 0.1332 | 0.019* | |
H9B | −0.0944 | −0.2121 | 0.0864 | 0.019* | |
N9 | 0.3208 (3) | −0.4801 (2) | 0.27536 (10) | 0.0158 (5) | |
C10 | −0.0577 (3) | −0.0308 (2) | 0.09506 (11) | 0.0135 (6) | |
C11 | 0.0822 (3) | −0.0026 (3) | 0.07770 (12) | 0.0172 (6) | |
H11A | 0.1597 | −0.0616 | 0.0805 | 0.021* | |
C12 | 0.1095 (3) | 0.1086 (3) | 0.05663 (12) | 0.0160 (6) | |
H12A | 0.2053 | 0.1269 | 0.0456 | 0.019* | |
C13 | −0.0052 (3) | 0.1935 (3) | 0.05177 (11) | 0.0143 (6) | |
C14 | −0.1456 (3) | 0.1690 (2) | 0.06776 (12) | 0.0154 (6) | |
H14A | −0.2236 | 0.2277 | 0.0639 | 0.018* | |
C15 | −0.1698 (3) | 0.0563 (3) | 0.08968 (12) | 0.0144 (6) | |
H15A | −0.2653 | 0.0387 | 0.1012 | 0.017* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.02508 (18) | 0.01611 (17) | 0.02264 (18) | −0.00447 (12) | 0.00320 (12) | 0.00557 (12) |
N1 | 0.0154 (12) | 0.0131 (12) | 0.0146 (12) | −0.0010 (9) | 0.0031 (9) | −0.0009 (10) |
C2 | 0.0195 (15) | 0.0130 (14) | 0.0141 (14) | −0.0035 (11) | 0.0051 (11) | −0.0015 (11) |
N3 | 0.0194 (13) | 0.0120 (12) | 0.0140 (12) | −0.0001 (10) | 0.0055 (10) | −0.0004 (9) |
C4 | 0.0170 (14) | 0.0139 (14) | 0.0119 (13) | 0.0002 (11) | 0.0066 (11) | 0.0019 (11) |
C5 | 0.0140 (14) | 0.0116 (14) | 0.0141 (14) | −0.0013 (11) | 0.0044 (11) | −0.0023 (11) |
N6 | 0.0198 (13) | 0.0106 (12) | 0.0182 (13) | −0.0015 (10) | −0.0033 (10) | 0.0012 (10) |
C6 | 0.0166 (14) | 0.0134 (14) | 0.0126 (13) | 0.0001 (11) | 0.0047 (11) | −0.0005 (11) |
N7 | 0.0200 (13) | 0.0104 (12) | 0.0121 (12) | −0.0012 (10) | 0.0011 (9) | −0.0004 (9) |
C8 | 0.0191 (15) | 0.0150 (15) | 0.0133 (13) | 0.0008 (12) | 0.0018 (11) | 0.0022 (11) |
C9 | 0.0175 (15) | 0.0127 (14) | 0.0161 (14) | −0.0018 (11) | −0.0029 (11) | −0.0010 (11) |
N9 | 0.0196 (13) | 0.0123 (12) | 0.0150 (12) | 0.0012 (10) | 0.0014 (9) | 0.0022 (10) |
C10 | 0.0167 (14) | 0.0132 (14) | 0.0097 (13) | −0.0014 (11) | −0.0014 (10) | −0.0021 (11) |
C11 | 0.0149 (14) | 0.0187 (15) | 0.0174 (14) | 0.0038 (12) | 0.0005 (11) | −0.0032 (12) |
C12 | 0.0131 (14) | 0.0212 (15) | 0.0135 (13) | −0.0016 (12) | 0.0017 (11) | −0.0026 (12) |
C13 | 0.0201 (15) | 0.0112 (13) | 0.0113 (13) | −0.0026 (11) | 0.0010 (11) | 0.0022 (11) |
C14 | 0.0140 (14) | 0.0139 (14) | 0.0170 (14) | 0.0015 (11) | −0.0017 (11) | 0.0000 (11) |
C15 | 0.0139 (14) | 0.0153 (14) | 0.0137 (13) | −0.0016 (11) | 0.0008 (11) | −0.0010 (11) |
Geometric parameters (Å, º) top
Br1—C13 | 1.913 (3) | C8—N9 | 1.323 (4) |
N1—C2 | 1.345 (4) | C8—H8A | 0.950 |
N1—C6 | 1.357 (4) | C9—C10 | 1.510 (4) |
C2—N3 | 1.336 (4) | C9—H9A | 0.990 |
C2—H2A | 0.950 | C9—H9B | 0.990 |
N3—C4 | 1.355 (4) | C10—C15 | 1.387 (4) |
C4—N9 | 1.381 (4) | C10—C11 | 1.403 (4) |
C4—C5 | 1.396 (4) | C11—C12 | 1.377 (4) |
C5—N7 | 1.386 (4) | C11—H11A | 0.950 |
C5—C6 | 1.413 (4) | C12—C13 | 1.386 (4) |
N6—C6 | 1.343 (4) | C12—H12A | 0.950 |
N6—C9 | 1.464 (4) | C13—C14 | 1.385 (4) |
N6—H6A | 0.880 | C14—C15 | 1.394 (4) |
N7—C8 | 1.353 (4) | C14—H14A | 0.950 |
N7—H7A | 0.880 | C15—H15A | 0.950 |
| | | |
C2—N1—C6 | 118.5 (2) | N6—C9—H9A | 109.5 |
N3—C2—N1 | 128.9 (3) | C10—C9—H9A | 109.5 |
N3—C2—H2A | 115.5 | N6—C9—H9B | 109.5 |
N1—C2—H2A | 115.5 | C10—C9—H9B | 109.5 |
C2—N3—C4 | 112.3 (2) | H9A—C9—H9B | 108.1 |
N3—C4—N9 | 125.0 (3) | C8—N9—C4 | 103.9 (2) |
N3—C4—C5 | 124.4 (3) | C15—C10—C11 | 118.2 (3) |
N9—C4—C5 | 110.6 (2) | C15—C10—C9 | 120.9 (3) |
N7—C5—C4 | 105.3 (2) | C11—C10—C9 | 121.0 (3) |
N7—C5—C6 | 136.3 (3) | C12—C11—C10 | 121.4 (3) |
C4—C5—C6 | 118.4 (3) | C12—C11—H11A | 119.3 |
C6—N6—C9 | 122.0 (2) | C10—C11—H11A | 119.3 |
C6—N6—H6A | 119.0 | C11—C12—C13 | 118.9 (3) |
C9—N6—H6A | 119.0 | C11—C12—H12A | 120.5 |
N6—C6—N1 | 119.3 (3) | C13—C12—H12A | 120.5 |
N6—C6—C5 | 123.3 (3) | C14—C13—C12 | 121.6 (3) |
N1—C6—C5 | 117.4 (2) | C14—C13—Br1 | 119.0 (2) |
C8—N7—C5 | 106.1 (2) | C12—C13—Br1 | 119.4 (2) |
C8—N7—H7A | 126.9 | C13—C14—C15 | 118.4 (3) |
C5—N7—H7A | 126.9 | C13—C14—H14A | 120.8 |
N9—C8—N7 | 114.2 (3) | C15—C14—H14A | 120.8 |
N9—C8—H8A | 122.9 | C10—C15—C14 | 121.5 (3) |
N7—C8—H8A | 122.9 | C10—C15—H15A | 119.2 |
N6—C9—C10 | 110.9 (2) | C14—C15—H15A | 119.2 |
| | | |
C6—N1—C2—N3 | −1.0 (4) | C5—N7—C8—N9 | 0.7 (3) |
N1—C2—N3—C4 | 1.7 (4) | C6—N6—C9—C10 | −159.1 (3) |
C2—N3—C4—N9 | 178.7 (3) | N7—C8—N9—C4 | −0.6 (3) |
C2—N3—C4—C5 | −0.5 (4) | N3—C4—N9—C8 | −179.0 (3) |
N3—C4—C5—N7 | 179.4 (2) | C5—C4—N9—C8 | 0.2 (3) |
N9—C4—C5—N7 | 0.1 (3) | N6—C9—C10—C15 | −130.4 (3) |
N3—C4—C5—C6 | −1.2 (4) | N6—C9—C10—C11 | 50.8 (3) |
N9—C4—C5—C6 | 179.5 (2) | C15—C10—C11—C12 | 1.0 (4) |
C9—N6—C6—N1 | 1.4 (4) | C9—C10—C11—C12 | 179.7 (3) |
C9—N6—C6—C5 | −179.6 (3) | C10—C11—C12—C13 | −1.0 (4) |
C2—N1—C6—N6 | 178.1 (3) | C11—C12—C13—C14 | 0.2 (4) |
C2—N1—C6—C5 | −0.9 (4) | C11—C12—C13—Br1 | −179.1 (2) |
N7—C5—C6—N6 | 2.1 (5) | C12—C13—C14—C15 | 0.6 (4) |
C4—C5—C6—N6 | −177.0 (3) | Br1—C13—C14—C15 | 179.9 (2) |
N7—C5—C6—N1 | −179.0 (3) | C11—C10—C15—C14 | −0.1 (4) |
C4—C5—C6—N1 | 1.9 (4) | C9—C10—C15—C14 | −178.9 (2) |
C4—C5—N7—C8 | −0.5 (3) | C13—C14—C15—C10 | −0.7 (4) |
C6—C5—N7—C8 | −179.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N6—H6A···N9i | 0.88 | 2.07 | 2.935 (3) | 166 |
N7—H7A···N3i | 0.88 | 2.01 | 2.856 (3) | 161 |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |