2-Chloro-6-[(2,6-dimethoxy­benz­yl)amino]-9-isopropyl­purine 0.125-hydrate

The secondary structure in the title compound, C₁₇H₂₀ClN₅O₂·0.125H₂O, is stabilized by N—H...N hydrogen bonds that connect mol­ecules into centrosymmetric dimers; the dimers are linked via a variety of inter­molecular inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 109 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in solvent or counterion
• R factor = 0.036
• wR factor = 0.087
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H6A    ..  H3V     ..       2.01 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      12.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8A    ..  O3      ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A    ..  O2      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19C   ..  N1      ..       2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16A   ..  N3      ..       2.71 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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, 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.

2-Chloro-6-[(2,6-dimethoxybenzyl)amino]-9-isopropylpurine 0.125-hydrate

Crystal data

C17H20ClN5O2·0.125H2O	F(000) = 1530
Mr = 364.08	Dx = 1.369 Mg m^−3
Monoclinic, C2/c	Melting point = 398.3–399.3 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 27.159 (5) Å	Cell parameters from 6240 reflections
b = 11.931 (2) Å	θ = 1.6–30.5°
c = 11.785 (2) Å	µ = 0.24 mm^−1
β = 112.32 (3)°	T = 109 K
V = 3532.6 (12) Å^3	Prism, colourless
Z = 8	0.35 × 0.25 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur2 diffractometer	2808 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Enhance (Oxford Diffraction) monochromator	θmax = 25.0°, θmin = 2.9°
Detector resolution: 16.3 pixels mm^-1	h = −32→32
ω scans	k = −14→14
13528 measured reflections	l = −14→13
3099 independent 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.035P)^2 + 5P] where P = (Fo^2 + 2Fc^2)/3
3099 reflections	(Δ/σ)max = 0.002
239 parameters	Δρmax = 0.25 e Å^−3
4 restraints	Δρmin = −0.22 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	Occ. (<1)
Cl1	0.705748 (16)	0.19804 (4)	0.62131 (4)	0.02781 (14)
O1	0.44644 (5)	0.28631 (10)	0.27419 (11)	0.0271 (3)
O2	0.44794 (5)	0.06237 (10)	0.59774 (10)	0.0235 (3)
N1	0.61133 (5)	0.22264 (11)	0.62130 (12)	0.0183 (3)
N3	0.68545 (5)	0.28863 (12)	0.79865 (12)	0.0190 (3)
N6	0.52347 (5)	0.24338 (12)	0.59943 (12)	0.0187 (3)
H6A	0.4998	0.2758	0.6231	0.022*
N7	0.56714 (5)	0.34981 (12)	0.85358 (12)	0.0191 (3)
N9	0.65555 (5)	0.37486 (11)	0.95019 (12)	0.0172 (3)
C2	0.66201 (6)	0.24180 (14)	0.69022 (15)	0.0192 (4)
C4	0.64794 (6)	0.32274 (13)	0.84088 (14)	0.0167 (3)
C5	0.59353 (6)	0.30978 (14)	0.78232 (14)	0.0165 (3)
C6	0.57475 (6)	0.25819 (13)	0.66608 (14)	0.0170 (3)
C8	0.60566 (6)	0.38707 (14)	0.95192 (15)	0.0189 (4)
H8A	0.5995	0.4198	1.0189	0.023*
C9	0.50478 (6)	0.17529 (14)	0.48825 (15)	0.0188 (4)
H9A	0.5190	0.0983	0.5082	0.023*
H9B	0.5183	0.2071	0.4281	0.023*
C10	0.44508 (6)	0.17101 (13)	0.43225 (14)	0.0166 (3)
C11	0.41632 (7)	0.22614 (14)	0.32273 (15)	0.0199 (4)
C12	0.36119 (7)	0.21817 (15)	0.26952 (16)	0.0247 (4)
H12A	0.3420	0.2547	0.1940	0.030*
C13	0.33470 (7)	0.15659 (15)	0.32767 (17)	0.0273 (4)
H13A	0.2970	0.1515	0.2917	0.033*
C14	0.36183 (7)	0.10211 (15)	0.43714 (17)	0.0247 (4)
H14A	0.3432	0.0599	0.4764	0.030*
C15	0.41684 (7)	0.11026 (14)	0.48859 (15)	0.0195 (4)
C16	0.70704 (7)	0.40960 (15)	1.04549 (14)	0.0212 (4)
H16A	0.7292	0.3413	1.0785	0.025*
C17	0.73660 (7)	0.48659 (17)	0.99012 (16)	0.0295 (4)
H17A	0.7424	0.4477	0.9230	0.044*
H17B	0.7710	0.5073	1.0533	0.044*
H17C	0.7154	0.5544	0.9584	0.044*
C18	0.69786 (8)	0.46835 (16)	1.14968 (16)	0.0278 (4)
H18A	0.6800	0.4171	1.1867	0.042*
H18B	0.6755	0.5346	1.1180	0.042*
H18C	0.7321	0.4914	1.2118	0.042*
C19	0.41943 (8)	0.35514 (18)	0.17025 (17)	0.0349 (5)
H19A	0.4455	0.3985	0.1495	0.052*
H19B	0.3955	0.4065	0.1893	0.052*
H19C	0.3987	0.3078	0.1004	0.052*
C20	0.42197 (8)	−0.00429 (17)	0.65928 (18)	0.0326 (5)
H20A	0.4486	−0.0351	0.7348	0.049*
H20B	0.4028	−0.0658	0.6056	0.049*
H20C	0.3968	0.0423	0.6796	0.049*
O3	0.5192 (8)	0.4922 (12)	1.0747 (19)	0.124 (9)	0.125
H3V	0.5070	0.5589	1.0985	0.185*	0.125
H3W	0.5293	0.4226	1.1182	0.185*	0.125

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0180 (2)	0.0382 (3)	0.0291 (2)	0.00025 (18)	0.01094 (18)	−0.01112 (19)
O1	0.0298 (7)	0.0301 (7)	0.0233 (6)	0.0039 (5)	0.0121 (6)	0.0087 (5)
O2	0.0243 (6)	0.0240 (7)	0.0227 (6)	−0.0005 (5)	0.0094 (5)	0.0062 (5)
N1	0.0161 (7)	0.0205 (7)	0.0180 (7)	0.0005 (6)	0.0064 (6)	−0.0011 (6)
N3	0.0173 (7)	0.0217 (8)	0.0181 (7)	0.0008 (6)	0.0068 (6)	−0.0006 (6)
N6	0.0154 (7)	0.0225 (7)	0.0180 (7)	0.0001 (6)	0.0062 (6)	−0.0045 (6)
N7	0.0185 (7)	0.0218 (7)	0.0180 (7)	−0.0017 (6)	0.0083 (6)	0.0001 (6)
N9	0.0172 (7)	0.0196 (7)	0.0142 (7)	−0.0023 (6)	0.0054 (5)	−0.0001 (5)
C2	0.0182 (8)	0.0190 (9)	0.0218 (9)	0.0021 (7)	0.0091 (7)	−0.0001 (7)
C4	0.0176 (8)	0.0173 (8)	0.0155 (8)	−0.0009 (6)	0.0065 (7)	0.0018 (6)
C5	0.0177 (8)	0.0174 (8)	0.0160 (8)	−0.0002 (6)	0.0081 (7)	0.0021 (6)
C6	0.0182 (8)	0.0154 (8)	0.0170 (8)	0.0004 (7)	0.0061 (7)	0.0033 (6)
C8	0.0215 (9)	0.0190 (9)	0.0175 (8)	−0.0019 (7)	0.0089 (7)	0.0006 (7)
C9	0.0193 (8)	0.0202 (9)	0.0177 (8)	−0.0002 (7)	0.0080 (7)	−0.0023 (7)
C10	0.0171 (8)	0.0159 (8)	0.0166 (8)	0.0006 (6)	0.0061 (7)	−0.0044 (6)
C11	0.0239 (9)	0.0175 (9)	0.0179 (8)	0.0018 (7)	0.0077 (7)	−0.0037 (7)
C12	0.0238 (9)	0.0235 (9)	0.0194 (9)	0.0056 (7)	−0.0002 (7)	−0.0031 (7)
C13	0.0167 (9)	0.0265 (10)	0.0333 (10)	−0.0015 (7)	0.0034 (8)	−0.0081 (8)
C14	0.0197 (9)	0.0214 (9)	0.0346 (10)	−0.0043 (7)	0.0121 (8)	−0.0030 (8)
C15	0.0218 (9)	0.0159 (8)	0.0201 (8)	0.0010 (7)	0.0074 (7)	−0.0022 (7)
C16	0.0195 (8)	0.0234 (9)	0.0161 (8)	−0.0025 (7)	0.0013 (7)	−0.0011 (7)
C17	0.0208 (9)	0.0447 (12)	0.0227 (9)	−0.0117 (8)	0.0079 (8)	−0.0056 (8)
C18	0.0322 (10)	0.0318 (10)	0.0199 (9)	−0.0116 (8)	0.0106 (8)	−0.0054 (8)
C19	0.0452 (12)	0.0349 (11)	0.0274 (10)	0.0148 (9)	0.0170 (9)	0.0136 (8)
C20	0.0386 (11)	0.0321 (11)	0.0330 (11)	−0.0012 (9)	0.0202 (9)	0.0096 (8)
O3	0.13 (2)	0.087 (14)	0.19 (2)	−0.021 (14)	0.102 (18)	−0.046 (18)

Geometric parameters (Å, º)

Cl1—C2	1.7538 (17)	C10—C11	1.394 (2)
O1—C11	1.366 (2)	C11—C12	1.390 (2)
O1—C19	1.425 (2)	C12—C13	1.379 (3)
O1—O3^i	2.968 (16)	C12—H12A	0.9500
O2—C15	1.367 (2)	C13—C14	1.381 (3)
O2—C20	1.430 (2)	C13—H13A	0.9500
O2—N6	2.9735 (18)	C14—C15	1.386 (2)
N1—C2	1.326 (2)	C14—H14A	0.9500
N1—C6	1.358 (2)	C16—C18	1.514 (2)
N3—C2	1.316 (2)	C16—C17	1.520 (2)
N3—C4	1.355 (2)	C16—H16A	1.0000
N6—C6	1.325 (2)	C17—H17A	0.9800
N6—C9	1.459 (2)	C17—H17B	0.9800
N6—H6A	0.8800	C17—H17C	0.9800
N7—C8	1.309 (2)	C18—H18A	0.9800
N7—C5	1.380 (2)	C18—H18B	0.9800
N9—C8	1.371 (2)	C18—H18C	0.9800
N9—C4	1.374 (2)	C19—H19A	0.9800
N9—C16	1.482 (2)	C19—H19B	0.9800
C4—C5	1.382 (2)	C19—H19C	0.9800
C5—C6	1.409 (2)	C20—H20A	0.9800
C8—H8A	0.9500	C20—H20B	0.9800
C9—C10	1.502 (2)	C20—H20C	0.9800
C9—H9A	0.9900	O3—O3^ii	1.68 (4)
C9—H9B	0.9900	O3—H3V	0.945 (14)
C10—C15	1.393 (2)	O3—H3W	0.958 (15)
C11—O1—C19	117.91 (14)	C13—C12—C11	119.23 (16)
C11—O1—O3^i	106.6 (3)	C13—C12—H12A	120.4
C19—O1—O3^i	88.9 (4)	C11—C12—H12A	120.4
C15—O2—C20	117.53 (14)	C12—C13—C14	121.39 (16)
C15—O2—N6	83.16 (9)	C12—C13—H13A	119.3
C20—O2—N6	150.75 (11)	C14—C13—H13A	119.3
C2—N1—C6	116.79 (14)	C13—C14—C15	118.66 (16)
C2—N3—C4	109.28 (14)	C13—C14—H14A	120.7
C6—N6—C9	122.36 (14)	C15—C14—H14A	120.7
C6—N6—O2	131.89 (11)	O2—C15—C14	124.08 (15)
C9—N6—O2	65.53 (8)	O2—C15—C10	114.24 (14)
C6—N6—H6A	118.8	C14—C15—C10	121.67 (16)
C9—N6—H6A	118.8	N9—C16—C18	110.20 (14)
O2—N6—H6A	74.8	N9—C16—C17	110.11 (13)
C8—N7—C5	103.36 (13)	C18—C16—C17	110.16 (15)
C8—N9—C4	105.34 (13)	N9—C16—H16A	108.8
C8—N9—C16	127.80 (14)	C18—C16—H16A	108.8
C4—N9—C16	126.86 (13)	C17—C16—H16A	108.8
N3—C2—N1	132.45 (15)	C16—C17—H17A	109.5
N3—C2—Cl1	114.39 (12)	C16—C17—H17B	109.5
N1—C2—Cl1	113.15 (12)	H17A—C17—H17B	109.5
N3—C4—N9	127.89 (14)	C16—C17—H17C	109.5
N3—C4—C5	126.41 (15)	H17A—C17—H17C	109.5
N9—C4—C5	105.69 (14)	H17B—C17—H17C	109.5
N7—C5—C4	111.19 (14)	C16—C18—H18A	109.5
N7—C5—C6	131.54 (15)	C16—C18—H18B	109.5
C4—C5—C6	117.26 (15)	H18A—C18—H18B	109.5
N6—C6—N1	119.16 (14)	C16—C18—H18C	109.5
N6—C6—C5	123.04 (15)	H18A—C18—H18C	109.5
N1—C6—C5	117.80 (14)	H18B—C18—H18C	109.5
N7—C8—N9	114.39 (14)	O1—C19—H19A	109.5
N7—C8—H8A	122.8	O1—C19—H19B	109.5
N9—C8—H8A	122.8	H19A—C19—H19B	109.5
N6—C9—C10	111.28 (13)	O1—C19—H19C	109.5
N6—C9—H9A	109.4	H19A—C19—H19C	109.5
C10—C9—H9A	109.4	H19B—C19—H19C	109.5
N6—C9—H9B	109.4	O2—C20—H20A	109.5
C10—C9—H9B	109.4	O2—C20—H20B	109.5
H9A—C9—H9B	108.0	H20A—C20—H20B	109.5
C15—C10—C11	118.07 (15)	O2—C20—H20C	109.5
C15—C10—C9	120.42 (14)	H20A—C20—H20C	109.5
C11—C10—C9	121.51 (15)	H20B—C20—H20C	109.5
O1—C11—C12	124.11 (15)	O3^ii—O3—H3V	93.9 (15)
O1—C11—C10	114.94 (14)	O3^ii—O3—H3W	126 (2)
C12—C11—C10	120.95 (16)	H3V—O3—H3W	129 (2)
C15—O2—N6—C6	−165.63 (16)	C16—N9—C8—N7	179.02 (14)
C20—O2—N6—C6	56.7 (3)	C6—N6—C9—C10	178.97 (14)
C15—O2—N6—C9	−53.19 (12)	O2—N6—C9—C10	53.50 (11)
C20—O2—N6—C9	169.2 (2)	N6—C9—C10—C15	−71.48 (19)
C4—N3—C2—N1	−1.0 (3)	N6—C9—C10—C11	109.15 (17)
C4—N3—C2—Cl1	177.73 (11)	C19—O1—C11—C12	7.3 (2)
C6—N1—C2—N3	1.3 (3)	O3^i—O1—C11—C12	105.1 (5)
C6—N1—C2—Cl1	−177.46 (12)	C19—O1—C11—C10	−172.87 (15)
C2—N3—C4—N9	179.69 (16)	O3^i—O1—C11—C10	−75.1 (5)
C2—N3—C4—C5	1.0 (2)	C15—C10—C11—O1	178.44 (14)
C8—N9—C4—N3	−177.27 (16)	C9—C10—C11—O1	−2.2 (2)
C16—N9—C4—N3	2.5 (3)	C15—C10—C11—C12	−1.8 (2)
C8—N9—C4—C5	1.60 (17)	C9—C10—C11—C12	177.63 (15)
C16—N9—C4—C5	−178.65 (14)	O1—C11—C12—C13	−178.87 (15)
C8—N7—C5—C4	0.79 (18)	C10—C11—C12—C13	1.3 (2)
C8—N7—C5—C6	179.35 (17)	C11—C12—C13—C14	−0.4 (3)
N3—C4—C5—N7	177.36 (15)	C12—C13—C14—C15	0.0 (3)
N9—C4—C5—N7	−1.54 (18)	C20—O2—C15—C14	2.9 (2)
N3—C4—C5—C6	−1.4 (2)	N6—O2—C15—C14	−155.27 (16)
N9—C4—C5—C6	179.68 (14)	C20—O2—C15—C10	−178.10 (14)
C9—N6—C6—N1	9.6 (2)	N6—O2—C15—C10	23.70 (13)
O2—N6—C6—N1	94.40 (17)	C13—C14—C15—O2	178.42 (15)
C9—N6—C6—C5	−170.57 (15)	C13—C14—C15—C10	−0.5 (3)
O2—N6—C6—C5	−85.75 (19)	C11—C10—C15—O2	−177.67 (14)
C2—N1—C6—N6	178.45 (15)	C9—C10—C15—O2	2.9 (2)
C2—N1—C6—C5	−1.4 (2)	C11—C10—C15—C14	1.3 (2)
N7—C5—C6—N6	3.2 (3)	C9—C10—C15—C14	−178.07 (15)
C4—C5—C6—N6	−178.33 (15)	C8—N9—C16—C18	−2.5 (2)
N7—C5—C6—N1	−176.96 (16)	C4—N9—C16—C18	177.79 (15)
C4—C5—C6—N1	1.5 (2)	C8—N9—C16—C17	−124.24 (17)
C5—N7—C8—N9	0.29 (18)	C4—N9—C16—C17	56.1 (2)
C4—N9—C8—N7	−1.23 (19)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N7^i	0.88	2.13	3.0016 (19)	170
O3—H3W···O1^i	0.96 (2)	2.01 (1)	2.968 (16)	174 (1)
O3—H3V···N6^iii	0.95 (1)	2.40 (1)	3.167 (14)	138 (1)
O3—H3V···N7^ii	0.95 (1)	2.53 (1)	3.358 (16)	146 (1)
C8—H8A···O3	0.95	2.65	3.429 (17)	140
C9—H9A···O2^iv	0.99	2.63	3.421 (2)	138
C19—H19C···N1^v	0.98	2.72	3.581 (3)	147
C16—H16A···N3^vi	1.00	2.71	3.663 (2)	160

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