2-Chloro-6-[(4-hydr­oxy-3,5-dimethoxybenzyl)amino]-9-isopropyl­purine

The structure of the title compound, C₁₇H₂₀ClN₅O₃, consists of discrete mol­ecules of a 6-(benzyl­amino)purine derivative. The secondary structure is stabilized by N—H...O hydrogen bonds connecting mol­ecules into centrosymmetric dimers and by weak inter­atomic contacts of the types C—H...Cl and C—H...O, and by π–π stacking inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 105 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.091
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT318_ALERT_2_C Check Hybridisation of  N6     in Main Residue .          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19B   ..  O2      ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19A   ..  O3      ..       2.72 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19B   ..  CL1     ..       2.90 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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, 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-[(4-hydroxy-3,5-dimethoxybenzyl)amino]-9-isopropylpurine

Crystal data

C17H20ClN5O3	F(000) = 792
Mr = 377.83	Dx = 1.455 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2514 reflections
a = 11.8410 (8) Å	θ = 2.4–24.7°
b = 13.5939 (9) Å	µ = 0.25 mm^−1
c = 12.1693 (8) Å	T = 105 K
β = 118.318 (7)°	Prism, colourless
V = 1724.4 (2) Å^3	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection

Oxford Xcalibur2 diffractometer	2608 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Enhance (Oxford Diffraction) monochromator	θmax = 25.0°, θmin = 3.3°
Detector resolution: 16.3 pixels mm^-1	h = −14→14
rotation method ω scans	k = −16→15
9956 measured reflections	l = −11→14
3045 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.091	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0402P)^2 + 0.896P] where P = (Fo^2 + 2Fc^2)/3
3045 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.25 e Å^−3
0 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
Cl1	0.33560 (5)	0.68334 (4)	0.53980 (5)	0.02502 (16)
O1	0.14206 (13)	0.54611 (10)	−0.30302 (12)	0.0192 (3)
O2	0.25292 (14)	0.37058 (10)	−0.22873 (12)	0.0184 (3)
H2	0.2306	0.3966	−0.2987	0.028*
O3	0.40492 (13)	0.32897 (10)	0.00783 (12)	0.0183 (3)
N1	0.42874 (16)	0.66353 (12)	0.38746 (15)	0.0162 (4)
N3	0.55840 (16)	0.60752 (12)	0.59947 (15)	0.0178 (4)
N6	0.49629 (15)	0.65831 (12)	0.23665 (15)	0.0156 (4)
H6A	0.5618	0.6595	0.2213	0.019*
N7	0.75173 (16)	0.58055 (12)	0.44735 (15)	0.0176 (4)
N9	0.76550 (16)	0.54526 (12)	0.63367 (15)	0.0167 (4)
C2	0.45628 (19)	0.64607 (15)	0.50515 (19)	0.0184 (4)
C4	0.64825 (19)	0.58941 (14)	0.56379 (18)	0.0158 (4)
C5	0.64054 (18)	0.60949 (14)	0.44919 (18)	0.0154 (4)
C6	0.52074 (19)	0.64456 (14)	0.35537 (18)	0.0154 (4)
C8	0.82222 (19)	0.54283 (15)	0.55913 (18)	0.0177 (4)
H8A	0.9053	0.5163	0.5855	0.021*
C9	0.36793 (19)	0.67139 (15)	0.13160 (18)	0.0174 (4)
H9A	0.3637	0.7353	0.0909	0.021*
H9B	0.3046	0.6729	0.1629	0.021*
C10	0.33311 (18)	0.58937 (14)	0.03602 (18)	0.0146 (4)
C11	0.25102 (18)	0.61000 (15)	−0.08920 (18)	0.0152 (4)
H11A	0.2158	0.6740	−0.1141	0.018*
C12	0.22145 (18)	0.53593 (15)	−0.17697 (18)	0.0151 (4)
C13	0.27512 (18)	0.44242 (14)	−0.14218 (18)	0.0145 (4)
C14	0.35533 (19)	0.42251 (14)	−0.01649 (18)	0.0152 (4)
C15	0.38341 (19)	0.49547 (14)	0.07242 (18)	0.0156 (4)
H15A	0.4371	0.4812	0.1583	0.019*
C16	0.81285 (19)	0.50807 (15)	0.76252 (18)	0.0185 (4)
H16A	0.7366	0.4867	0.7711	0.022*
C17	0.8976 (2)	0.41872 (17)	0.7850 (2)	0.0250 (5)
H17A	0.8524	0.3703	0.7187	0.038*
H17B	0.9180	0.3895	0.8660	0.038*
H17C	0.9771	0.4386	0.7850	0.038*
C18	0.8780 (2)	0.59050 (17)	0.8554 (2)	0.0291 (5)
H18A	0.8210	0.6477	0.8320	0.044*
H18B	0.9579	0.6086	0.8550	0.044*
H18C	0.8973	0.5684	0.9391	0.044*
C19	0.1135 (2)	0.64428 (15)	−0.35062 (19)	0.0206 (5)
H19A	0.0691	0.6425	−0.4421	0.031*
H19B	0.1935	0.6816	−0.3211	0.031*
H19C	0.0584	0.6760	−0.3213	0.031*
C20	0.4846 (2)	0.30536 (16)	0.13651 (18)	0.0211 (5)
H20A	0.5136	0.2370	0.1439	0.032*
H20B	0.4356	0.3137	0.1820	0.032*
H20C	0.5592	0.3492	0.1719	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0186 (3)	0.0385 (3)	0.0195 (3)	0.0044 (2)	0.0104 (2)	−0.0009 (2)
O1	0.0224 (8)	0.0163 (7)	0.0128 (7)	0.0037 (6)	0.0035 (6)	0.0016 (6)
O2	0.0238 (8)	0.0179 (7)	0.0134 (7)	0.0021 (6)	0.0087 (6)	0.0003 (6)
O3	0.0221 (7)	0.0158 (8)	0.0141 (7)	0.0041 (6)	0.0061 (6)	0.0019 (6)
N1	0.0172 (9)	0.0170 (9)	0.0153 (9)	−0.0005 (7)	0.0084 (7)	−0.0003 (7)
N3	0.0161 (9)	0.0204 (9)	0.0159 (9)	−0.0002 (7)	0.0068 (7)	−0.0015 (8)
N6	0.0132 (8)	0.0189 (9)	0.0150 (8)	−0.0009 (7)	0.0068 (7)	0.0007 (7)
N7	0.0184 (9)	0.0175 (9)	0.0171 (9)	0.0012 (7)	0.0086 (8)	0.0005 (8)
N9	0.0168 (9)	0.0191 (9)	0.0132 (8)	0.0010 (7)	0.0062 (7)	0.0004 (7)
C2	0.0176 (10)	0.0180 (11)	0.0200 (11)	−0.0009 (9)	0.0094 (9)	−0.0018 (9)
C4	0.0162 (10)	0.0150 (10)	0.0145 (10)	−0.0021 (8)	0.0057 (8)	−0.0014 (8)
C5	0.0160 (10)	0.0128 (10)	0.0156 (10)	−0.0016 (8)	0.0061 (9)	−0.0011 (8)
C6	0.0189 (10)	0.0101 (10)	0.0171 (10)	−0.0038 (8)	0.0084 (9)	−0.0011 (8)
C8	0.0171 (10)	0.0177 (10)	0.0191 (11)	0.0010 (9)	0.0092 (9)	0.0000 (9)
C9	0.0164 (10)	0.0167 (10)	0.0172 (10)	0.0016 (8)	0.0062 (9)	0.0012 (9)
C10	0.0134 (9)	0.0162 (10)	0.0168 (10)	−0.0009 (8)	0.0093 (8)	−0.0009 (9)
C11	0.0137 (9)	0.0131 (10)	0.0199 (10)	0.0021 (8)	0.0087 (9)	0.0017 (8)
C12	0.0128 (9)	0.0194 (10)	0.0133 (10)	−0.0007 (8)	0.0062 (8)	0.0020 (9)
C13	0.0146 (10)	0.0141 (10)	0.0171 (10)	−0.0026 (8)	0.0093 (8)	−0.0018 (8)
C14	0.0138 (9)	0.0143 (10)	0.0191 (10)	0.0007 (8)	0.0093 (8)	0.0021 (9)
C15	0.0148 (10)	0.0183 (10)	0.0144 (10)	0.0001 (8)	0.0074 (8)	0.0025 (9)
C16	0.0178 (10)	0.0230 (11)	0.0119 (10)	−0.0003 (9)	0.0048 (9)	0.0017 (9)
C17	0.0249 (11)	0.0259 (12)	0.0202 (11)	0.0039 (10)	0.0073 (10)	0.0060 (10)
C18	0.0325 (13)	0.0281 (13)	0.0201 (12)	−0.0024 (10)	0.0070 (10)	−0.0020 (10)
C19	0.0213 (11)	0.0186 (11)	0.0184 (11)	0.0029 (9)	0.0067 (9)	0.0045 (9)
C20	0.0248 (11)	0.0199 (11)	0.0152 (10)	0.0041 (9)	0.0067 (9)	0.0039 (9)

Geometric parameters (Å, º)

Cl1—C2	1.746 (2)	C9—H9B	0.9900
O1—C12	1.374 (2)	C10—C15	1.389 (3)
O1—C19	1.430 (2)	C10—C11	1.393 (3)
O2—C13	1.367 (2)	C11—C12	1.387 (3)
O2—H2	0.8400	C11—H11A	0.9500
O3—C14	1.373 (2)	C12—C13	1.394 (3)
O3—C20	1.430 (2)	C13—C14	1.392 (3)
N1—C2	1.331 (3)	C14—C15	1.387 (3)
N1—C6	1.345 (3)	C15—H15A	0.9500
N3—C2	1.318 (3)	C16—C17	1.515 (3)
N3—C4	1.349 (3)	C16—C18	1.517 (3)
N6—C6	1.345 (2)	C16—H16A	1.0000
N6—C9	1.460 (2)	C17—H17A	0.9800
N6—H6A	0.8800	C17—H17B	0.9800
N7—C8	1.316 (3)	C17—H17C	0.9800
N7—C5	1.385 (3)	C18—H18A	0.9800
N9—C8	1.361 (3)	C18—H18B	0.9800
N9—C4	1.375 (3)	C18—H18C	0.9800
N9—C16	1.481 (2)	C19—H19A	0.9800
C4—C5	1.381 (3)	C19—H19B	0.9800
C5—C6	1.417 (3)	C19—H19C	0.9800
C8—H8A	0.9500	C20—H20A	0.9800
C9—C10	1.520 (3)	C20—H20B	0.9800
C9—H9A	0.9900	C20—H20C	0.9800
C12—O1—C19	116.82 (15)	C11—C12—C13	121.07 (18)
C13—O2—H2	109.5	O2—C13—C14	119.29 (17)
C14—O3—C20	115.89 (15)	O2—C13—C12	121.60 (17)
C2—N1—C6	117.36 (17)	C14—C13—C12	119.09 (18)
C2—N3—C4	109.27 (17)	O3—C14—C15	125.06 (18)
C6—N6—C9	124.16 (17)	O3—C14—C13	114.60 (17)
C6—N6—H6A	117.9	C15—C14—C13	120.29 (18)
C9—N6—H6A	117.9	C14—C15—C10	120.03 (18)
C8—N7—C5	103.63 (16)	C14—C15—H15A	120.0
C8—N9—C4	105.73 (16)	C10—C15—H15A	120.0
C8—N9—C16	129.67 (17)	N9—C16—C17	110.53 (17)
C4—N9—C16	124.59 (16)	N9—C16—C18	109.87 (17)
N3—C2—N1	131.55 (19)	C17—C16—C18	113.47 (18)
N3—C2—Cl1	115.02 (15)	N9—C16—H16A	107.6
N1—C2—Cl1	113.42 (15)	C17—C16—H16A	107.6
N3—C4—N9	126.85 (17)	C18—C16—H16A	107.6
N3—C4—C5	127.20 (18)	C16—C17—H17A	109.5
N9—C4—C5	105.93 (17)	C16—C17—H17B	109.5
C4—C5—N7	110.63 (17)	H17A—C17—H17B	109.5
C4—C5—C6	116.21 (18)	C16—C17—H17C	109.5
N7—C5—C6	132.76 (18)	H17A—C17—H17C	109.5
N6—C6—N1	119.60 (18)	H17B—C17—H17C	109.5
N6—C6—C5	122.38 (18)	C16—C18—H18A	109.5
N1—C6—C5	118.02 (17)	C16—C18—H18B	109.5
N7—C8—N9	114.06 (17)	H18A—C18—H18B	109.5
N7—C8—H8A	123.0	C16—C18—H18C	109.5
N9—C8—H8A	123.0	H18A—C18—H18C	109.5
N6—C9—C10	111.86 (16)	H18B—C18—H18C	109.5
N6—C9—H9A	109.2	O1—C19—H19A	109.5
C10—C9—H9A	109.2	O1—C19—H19B	109.5
N6—C9—H9B	109.2	H19A—C19—H19B	109.5
C10—C9—H9B	109.2	O1—C19—H19C	109.5
H9A—C9—H9B	107.9	H19A—C19—H19C	109.5
C15—C10—C11	120.32 (18)	H19B—C19—H19C	109.5
C15—C10—C9	120.68 (17)	O3—C20—H20A	109.5
C11—C10—C9	118.99 (17)	O3—C20—H20B	109.5
C12—C11—C10	119.13 (18)	H20A—C20—H20B	109.5
C12—C11—H11A	120.4	O3—C20—H20C	109.5
C10—C11—H11A	120.4	H20A—C20—H20C	109.5
O1—C12—C11	125.17 (18)	H20B—C20—H20C	109.5
O1—C12—C13	113.75 (17)
C4—N3—C2—N1	3.7 (3)	C6—N6—C9—C10	−117.4 (2)
C4—N3—C2—Cl1	−174.96 (14)	N6—C9—C10—C15	29.9 (3)
C6—N1—C2—N3	−4.0 (3)	N6—C9—C10—C11	−149.31 (17)
C6—N1—C2—Cl1	174.68 (14)	C15—C10—C11—C12	−0.7 (3)
C2—N3—C4—N9	−176.75 (19)	C9—C10—C11—C12	178.51 (17)
C2—N3—C4—C5	1.9 (3)	C19—O1—C12—C11	16.1 (3)
C8—N9—C4—N3	179.92 (19)	C19—O1—C12—C13	−162.32 (16)
C16—N9—C4—N3	0.9 (3)	C10—C11—C12—O1	179.95 (18)
C8—N9—C4—C5	1.1 (2)	C10—C11—C12—C13	−1.7 (3)
C16—N9—C4—C5	−177.91 (18)	O1—C12—C13—O2	2.6 (3)
N3—C4—C5—N7	179.92 (18)	C11—C12—C13—O2	−175.92 (17)
N9—C4—C5—N7	−1.2 (2)	O1—C12—C13—C14	−178.75 (17)
N3—C4—C5—C6	−6.3 (3)	C11—C12—C13—C14	2.7 (3)
N9—C4—C5—C6	172.54 (17)	C20—O3—C14—C15	4.3 (3)
C8—N7—C5—C4	0.9 (2)	C20—O3—C14—C13	−178.16 (16)
C8—N7—C5—C6	−171.5 (2)	O2—C13—C14—O3	−0.3 (3)
C9—N6—C6—N1	−14.5 (3)	C12—C13—C14—O3	−178.97 (16)
C9—N6—C6—C5	164.80 (18)	O2—C13—C14—C15	177.35 (17)
C2—N1—C6—N6	178.10 (18)	C12—C13—C14—C15	−1.3 (3)
C2—N1—C6—C5	−1.3 (3)	O3—C14—C15—C10	176.33 (17)
C4—C5—C6—N6	−173.70 (18)	C13—C14—C15—C10	−1.1 (3)
N7—C5—C6—N6	−1.7 (3)	C11—C10—C15—C14	2.1 (3)
C4—C5—C6—N1	5.6 (3)	C9—C10—C15—C14	−177.13 (17)
N7—C5—C6—N1	177.70 (19)	C8—N9—C16—C17	−31.2 (3)
C5—N7—C8—N9	−0.2 (2)	C4—N9—C16—C17	147.50 (19)
C4—N9—C8—N7	−0.6 (2)	C8—N9—C16—C18	94.8 (2)
C16—N9—C8—N7	178.32 (19)	C4—N9—C16—C18	−86.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N7^i	0.84	1.94	2.717 (2)	153
N6—H6A···O2^i	0.88	2.19	3.042 (2)	163
C8—H8A···O1^ii	0.95	2.50	3.336 (2)	147
C19—H19B···O2^iii	0.98	2.65	3.383 (2)	132
C19—H19A···O3^iii	0.98	2.72	3.101 (2)	104
C19—H19B···Cl1^iv	0.98	2.90	3.507 (2)	121

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