6-(2-Bromo­benzyl­amino)purine monohydrate

Trávníček, Z.; Rosenker, C.J.

doi:10.1107/S1600536806026419

6-(2-Bromobenzylamino)purine monohydrate

Z. Trávníček and C. J. Rosenker

The structure of the title compound, C₁₂H₁₂N₅BrO·H₂O, consists of discrete molecules connected by N—H

N hydrogen bonds to form centrosymmetric dimers, with an N

N distance of 2.839 (4) Å. The solvent water molecules are linked by intermolecular O—H

O hydrogen bonds into infinite chains along the [001] direction. The water molecules with disordered H atoms also participate in O—H

O, N—H

O and O—H

N hydrogen bonds, with O

O, N

O and O

N distances of 2.728 (5) and 2.732 (5), 3.107 (3) and 2.748 (3) Å, respectively. In addition to conventional hydrogen bonds, there are several weak interatomic contacts of the type C

Br, and π-stacking interactions of the types C

C and N

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026419/sg2044sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026419/sg2044Isup2.hkl Contains datablock I

CCDC reference: 618327

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Key indicators

Single-crystal X-ray study
T = 110 K
Mean (C-C) = 0.004 Å
R factor = 0.036
wR factor = 0.106
Data-to-parameter ratio = 12.1

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Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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: SIR2002 (Burla et al., 2002); 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-(2-Bromobenzylamino)purine monohydrate top

Crystal data top

C₁₂H₁₀BrN₅·H₂O	F(000) = 1296
M_r = 322.18	D_x = 1.721 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4064 reflections
a = 21.9381 (15) Å	θ = 1.6–27.8°
b = 15.1277 (15) Å	µ = 3.31 mm⁻¹
c = 7.6320 (5) Å	T = 110 K
β = 100.877 (9)°	Prism, colourless
V = 2487.4 (3) Å³	0.35 × 0.25 × 0.25 mm
Z = 8

Data collection top

Oxford Xcalibur diffractometer	2192 independent reflections
Radiation source: fine-focus sealed tube	2034 reflections with I > 2σ(I)
Enhance (Oxford Diffraction) monochromator	R_int = 0.042
Detector resolution: 16.3 pixels mm^-1	θ_max = 25.1°, θ_min = 2.7°
rotation method, ω scans	h = −25→26
Absorption correction: multi-scan (Blessing, 1995)	k = −17→17
T_min = 0.399, T_max = 0.438	l = −7→9
8154 measured 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0683P)² + 3.1343P] where P = (F_o² + 2F_c²)/3
2192 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.73 e Å⁻³
3 restraints	Δρ_min = −0.42 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)
Br1	0.819795 (14)	0.33487 (2)	0.70104 (4)	0.02083 (17)
O1	0.52859 (11)	0.43359 (15)	0.9250 (3)	0.0243 (5)
N1	0.64231 (13)	0.15140 (17)	0.8332 (4)	0.0172 (6)
N3	0.57099 (12)	0.04578 (17)	0.9157 (3)	0.0178 (5)
N6	0.63246 (12)	0.30367 (17)	0.8654 (3)	0.0166 (5)
H6A	0.6093	0.3488	0.8849	0.020*
N7	0.51217 (12)	0.25824 (17)	0.9981 (3)	0.0159 (5)
N9	0.48491 (12)	0.11728 (17)	1.0204 (3)	0.0161 (6)
H9A	0.4632	0.0711	1.0427	0.019*
C2	0.62110 (15)	0.0703 (2)	0.8545 (4)	0.0199 (7)
H2A	0.6453	0.0234	0.8211	0.024*
C4	0.53936 (14)	0.1164 (2)	0.9583 (4)	0.0147 (6)
C5	0.55561 (14)	0.20407 (19)	0.9439 (4)	0.0144 (6)
C6	0.61061 (14)	0.2209 (2)	0.8804 (4)	0.0149 (6)
C8	0.47120 (14)	0.2032 (2)	1.0407 (4)	0.0162 (6)
H8A	0.4351	0.2220	1.0821	0.019*
C9	0.69148 (16)	0.3211 (2)	0.8193 (4)	0.0174 (7)
H9B	0.7160	0.2657	0.8329	0.021*
H9C	0.7138	0.3646	0.9048	0.021*
C10	0.68845 (14)	0.35595 (19)	0.6315 (4)	0.0144 (6)
C12	0.74120 (16)	0.3994 (2)	0.3922 (4)	0.0219 (7)
H12A	0.7786	0.4050	0.3477	0.026*
C13	0.68472 (16)	0.4239 (2)	0.2884 (4)	0.0245 (8)
H13A	0.6833	0.4469	0.1719	0.029*
C14	0.63116 (16)	0.4149 (2)	0.3536 (4)	0.0229 (7)
H14A	0.5926	0.4315	0.2820	0.028*
C11	0.74175 (14)	0.36674 (19)	0.5612 (4)	0.0151 (6)
C15	0.63281 (15)	0.3814 (2)	0.5247 (4)	0.0188 (7)
H15A	0.5953	0.3760	0.5689	0.023*
H1W	0.520 (2)	0.378 (2)	0.951 (6)	0.050*
H1VA	0.507 (4)	0.440 (5)	0.809 (6)	0.050*	0.50
H1VB	0.506 (4)	0.480 (5)	0.958 (12)	0.050*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0130 (2)	0.0221 (2)	0.0275 (2)	−0.00032 (11)	0.00418 (15)	0.00068 (11)
O1	0.0280 (13)	0.0146 (11)	0.0311 (13)	−0.0022 (10)	0.0072 (10)	0.0003 (10)
N1	0.0162 (14)	0.0156 (12)	0.0213 (13)	0.0008 (10)	0.0070 (11)	0.0010 (10)
N3	0.0182 (13)	0.0155 (12)	0.0209 (13)	−0.0018 (11)	0.0063 (10)	0.0011 (10)
N6	0.0152 (13)	0.0120 (12)	0.0245 (13)	−0.0009 (10)	0.0090 (10)	−0.0010 (10)
N7	0.0164 (13)	0.0153 (13)	0.0175 (12)	0.0014 (10)	0.0067 (10)	0.0003 (10)
N9	0.0156 (13)	0.0127 (12)	0.0207 (13)	−0.0037 (10)	0.0051 (11)	0.0019 (10)
C2	0.0193 (16)	0.0205 (16)	0.0213 (15)	0.0036 (13)	0.0071 (13)	0.0006 (13)
C4	0.0148 (15)	0.0158 (15)	0.0131 (14)	−0.0003 (12)	0.0017 (12)	0.0015 (11)
C5	0.0166 (15)	0.0143 (15)	0.0121 (13)	−0.0020 (12)	0.0024 (11)	0.0018 (11)
C6	0.0154 (15)	0.0167 (14)	0.0128 (13)	−0.0012 (12)	0.0036 (11)	0.0019 (11)
C8	0.0163 (16)	0.0158 (15)	0.0176 (14)	0.0031 (12)	0.0063 (12)	0.0019 (12)
C9	0.0176 (16)	0.0189 (15)	0.0164 (15)	0.0012 (12)	0.0053 (12)	0.0031 (11)
C10	0.0161 (15)	0.0088 (13)	0.0190 (15)	−0.0020 (12)	0.0055 (12)	−0.0032 (11)
C12	0.0276 (18)	0.0177 (15)	0.0237 (16)	−0.0019 (13)	0.0136 (13)	0.0000 (13)
C13	0.040 (2)	0.0181 (17)	0.0164 (15)	0.0049 (14)	0.0072 (15)	0.0031 (12)
C14	0.0253 (17)	0.0181 (15)	0.0230 (16)	0.0072 (13)	−0.0015 (13)	−0.0009 (13)
C11	0.0163 (15)	0.0100 (14)	0.0186 (14)	−0.0010 (12)	0.0026 (12)	−0.0013 (11)
C15	0.0162 (16)	0.0157 (15)	0.0249 (16)	0.0012 (12)	0.0051 (13)	−0.0023 (12)

Geometric parameters (Å, º) top

Br1—C11	1.901 (3)	C4—C5	1.383 (4)
O1—H1W	0.89 (3)	C5—C6	1.406 (4)
O1—H1VA	0.93 (3)	C8—H8A	0.9500
O1—H1VB	0.92 (3)	C9—C10	1.517 (4)
N1—C2	1.333 (4)	C9—H9B	0.9900
N1—C6	1.347 (4)	C9—H9C	0.9900
N3—C2	1.326 (4)	C10—C11	1.385 (4)
N3—C4	1.346 (4)	C10—C15	1.388 (4)
N6—C6	1.353 (4)	C12—C11	1.379 (4)
N6—C9	1.429 (4)	C12—C13	1.389 (5)
N6—H6A	0.8800	C12—H12A	0.9500
N7—C8	1.311 (4)	C13—C14	1.367 (5)
N7—C5	1.378 (4)	C13—H13A	0.9500
N9—C8	1.349 (4)	C14—C15	1.395 (5)
N9—C4	1.366 (4)	C14—H14A	0.9500
N9—H9A	0.8800	C15—H15A	0.9500
C2—H2A	0.9500

H1W—O1—H1VA	103 (6)	N9—C8—H8A	123.0
H1W—O1—H1VB	120 (7)	N6—C9—C10	114.6 (3)
H1VA—O1—H1VB	89 (8)	N6—C9—H9B	108.6
C2—N1—C6	118.4 (3)	C10—C9—H9B	108.6
C2—N3—C4	111.2 (3)	N6—C9—H9C	108.6
C6—N6—C9	122.9 (3)	C10—C9—H9C	108.6
C6—N6—H6A	118.6	H9B—C9—H9C	107.6
C9—N6—H6A	118.6	C11—C10—C15	116.9 (3)
C8—N7—C5	104.0 (2)	C11—C10—C9	121.1 (3)
C8—N9—C4	106.1 (3)	C15—C10—C9	121.9 (3)
C8—N9—H9A	126.9	C11—C12—C13	118.6 (3)
C4—N9—H9A	126.9	C11—C12—H12A	120.7
N3—C2—N1	129.2 (3)	C13—C12—H12A	120.7
N3—C2—H2A	115.4	C14—C13—C12	120.1 (3)
N1—C2—H2A	115.4	C14—C13—H13A	119.9
N3—C4—N9	128.0 (3)	C12—C13—H13A	119.9
N3—C4—C5	126.1 (3)	C13—C14—C15	120.3 (3)
N9—C4—C5	105.8 (3)	C13—C14—H14A	119.8
N7—C5—C4	110.1 (3)	C15—C14—H14A	119.8
N7—C5—C6	133.1 (3)	C12—C11—C10	123.1 (3)
C4—C5—C6	116.9 (3)	C12—C11—Br1	117.6 (2)
N1—C6—N6	119.4 (3)	C10—C11—Br1	119.3 (2)
N1—C6—C5	118.1 (3)	C10—C15—C14	121.0 (3)
N6—C6—C5	122.5 (3)	C10—C15—H15A	119.5
N7—C8—N9	113.9 (3)	C14—C15—H15A	119.5
N7—C8—H8A	123.0

C4—N3—C2—N1	0.5 (5)	N7—C5—C6—N6	1.9 (5)
C6—N1—C2—N3	0.9 (5)	C4—C5—C6—N6	−178.0 (3)
C2—N3—C4—N9	178.1 (3)	C5—N7—C8—N9	0.7 (3)
C2—N3—C4—C5	−0.6 (4)	C4—N9—C8—N7	−0.4 (3)
C8—N9—C4—N3	−179.1 (3)	C6—N6—C9—C10	106.9 (3)
C8—N9—C4—C5	−0.2 (3)	N6—C9—C10—C11	−172.9 (3)
C8—N7—C5—C4	−0.8 (3)	N6—C9—C10—C15	9.4 (4)
C8—N7—C5—C6	179.4 (3)	C11—C12—C13—C14	−0.4 (5)
N3—C4—C5—N7	179.5 (3)	C12—C13—C14—C15	0.2 (5)
N9—C4—C5—N7	0.6 (3)	C13—C12—C11—C10	1.0 (5)
N3—C4—C5—C6	−0.6 (4)	C13—C12—C11—Br1	−179.4 (2)
N9—C4—C5—C6	−179.5 (2)	C15—C10—C11—C12	−1.3 (4)
C2—N1—C6—N6	177.8 (3)	C9—C10—C11—C12	−179.1 (3)
C2—N1—C6—C5	−2.1 (4)	C15—C10—C11—Br1	179.1 (2)
C9—N6—C6—N1	−6.8 (4)	C9—C10—C11—Br1	1.3 (4)
C9—N6—C6—C5	173.1 (3)	C11—C10—C15—C14	1.0 (4)
N7—C5—C6—N1	−178.2 (3)	C9—C10—C15—C14	178.8 (3)
C4—C5—C6—N1	2.0 (4)	C13—C14—C15—C10	−0.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O1	0.88	2.25	3.107 (4)	163
O1—H1W···N7	0.89 (3)	1.86 (3)	2.748 (3)	172 (5)
N9—H9A···N3ⁱ	0.88	1.97	2.838 (4)	169
O1—H1VA···O1ⁱⁱ	0.93 (3)	1.81 (3)	2.728 (5)	170 (8)
O1—H1VB···O1ⁱⁱⁱ	0.92 (3)	1.83 (3)	2.732 (5)	167 (9)

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, y, −z+3/2; (iii) −x+1, −y+1, −z+2.

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6-(2-Bromo­benzyl­amino)purine monohydrate

Supporting information

Key indicators

checkCIF/PLATON results

6-(2-Bromobenzylamino)purine monohydrate