N⁶-(4-Methoxy­benzo­yl)adenine

The mol­ecules of the title compound, C₁₃H₁₁N₅O₂, are linked into chains along the c axis by N—H...O and C—H...O hydrogen-bond contacts. N—H...N inter­actions connect the chains into two-dimensional layers. The packing is further stabilized by π–π inter­actions involving the purine system.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.120
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

N⁶-(4-Methoxybenzoyl)adenine

Crystal data

C13H11N5O2	F(000) = 560
Mr = 269.27	Dx = 1.442 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2936 reflections
a = 12.398 (3) Å	θ = 2.6–23.0°
b = 10.045 (3) Å	µ = 0.10 mm^−1
c = 10.079 (3) Å	T = 293 K
β = 98.804 (4)°	Block, colourless
V = 1240.5 (6) Å^3	0.32 × 0.17 × 0.05 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2446 independent reflections
Radiation source: fine-focus sealed tube	1634 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 1.7°
ω scans	h = −14→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→11
Tmin = 0.968, Tmax = 0.995	l = −10→12
6725 measured 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0521P)^2 + 0.1439P] where P = (Fo^2 + 2Fc^2)/3
2446 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.18 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
O1	0.72524 (13)	0.21529 (14)	0.73182 (14)	0.0488 (4)
N5	0.70257 (15)	0.29282 (16)	0.51996 (17)	0.0442 (5)
H5A	0.7033	0.2739	0.4369	0.053*
N4	0.70629 (16)	0.51967 (18)	0.48331 (19)	0.0508 (5)
C7	0.78499 (16)	0.0736 (2)	0.57086 (19)	0.0370 (5)
C2	0.60082 (16)	0.4499 (2)	0.6450 (2)	0.0377 (5)
N2	0.54201 (14)	0.38081 (16)	0.72660 (18)	0.0444 (5)
H2A	0.5388	0.2957	0.7348	0.053*
O2	0.96307 (14)	−0.25004 (16)	0.46960 (17)	0.0619 (5)
C6	0.73447 (17)	0.1969 (2)	0.6145 (2)	0.0379 (5)
C1	0.66873 (17)	0.4208 (2)	0.5525 (2)	0.0407 (5)
C11	0.88660 (19)	−0.1256 (2)	0.6401 (2)	0.0476 (6)
H11A	0.9149	−0.1846	0.7077	0.057*
C12	0.82743 (18)	−0.0160 (2)	0.6699 (2)	0.0431 (5)
H12A	0.8158	−0.0021	0.7578	0.052*
C8	0.79897 (18)	0.0471 (2)	0.4388 (2)	0.0469 (6)
H8A	0.7687	0.1042	0.3704	0.056*
C10	0.90348 (18)	−0.1472 (2)	0.5096 (2)	0.0444 (5)
N1	0.51004 (16)	0.59656 (17)	0.7601 (2)	0.0533 (5)
C4	0.57877 (17)	0.5841 (2)	0.6663 (2)	0.0429 (5)
C9	0.85701 (19)	−0.0625 (2)	0.4086 (2)	0.0514 (6)
H9A	0.8651	−0.0797	0.3199	0.062*
N3	0.61566 (16)	0.68576 (17)	0.5989 (2)	0.0539 (5)
C3	0.49034 (19)	0.4719 (2)	0.7913 (3)	0.0517 (6)
H3B	0.4446	0.4493	0.8528	0.062*
C5	0.6762 (2)	0.6448 (2)	0.5095 (2)	0.0552 (6)
H5B	0.7013	0.7113	0.4578	0.066*
C13	1.0177 (2)	−0.3348 (2)	0.5707 (3)	0.0714 (8)
H13A	1.0565	−0.4024	0.5300	0.107*
H13B	0.9653	−0.3758	0.6186	0.107*
H13C	1.0684	−0.2835	0.6319	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0677 (11)	0.0495 (9)	0.0297 (8)	0.0125 (8)	0.0092 (7)	−0.0012 (7)
N5	0.0653 (13)	0.0392 (10)	0.0284 (9)	0.0061 (9)	0.0081 (9)	−0.0023 (8)
N4	0.0643 (13)	0.0426 (11)	0.0462 (11)	−0.0057 (9)	0.0110 (10)	0.0047 (9)
C7	0.0432 (12)	0.0361 (11)	0.0317 (11)	−0.0018 (10)	0.0057 (9)	−0.0008 (10)
C2	0.0422 (12)	0.0319 (11)	0.0376 (11)	−0.0022 (9)	0.0023 (10)	−0.0016 (9)
N2	0.0534 (11)	0.0302 (9)	0.0515 (11)	0.0020 (8)	0.0143 (9)	−0.0005 (8)
O2	0.0741 (12)	0.0502 (10)	0.0621 (11)	0.0158 (9)	0.0125 (9)	−0.0099 (9)
C6	0.0427 (12)	0.0401 (12)	0.0311 (11)	−0.0028 (10)	0.0062 (9)	0.0009 (10)
C1	0.0503 (13)	0.0348 (11)	0.0352 (12)	−0.0009 (10)	0.0010 (10)	0.0000 (10)
C11	0.0624 (15)	0.0386 (12)	0.0403 (13)	0.0045 (11)	0.0027 (11)	0.0022 (10)
C12	0.0574 (14)	0.0403 (12)	0.0320 (11)	0.0000 (10)	0.0082 (10)	−0.0010 (10)
C8	0.0638 (15)	0.0439 (13)	0.0327 (12)	0.0051 (11)	0.0062 (11)	0.0024 (10)
C10	0.0490 (13)	0.0364 (12)	0.0481 (13)	0.0019 (10)	0.0081 (11)	−0.0074 (11)
N1	0.0604 (12)	0.0350 (11)	0.0663 (13)	0.0034 (9)	0.0156 (10)	−0.0064 (10)
C4	0.0461 (12)	0.0328 (11)	0.0475 (13)	−0.0013 (10)	−0.0003 (10)	−0.0028 (10)
C9	0.0714 (16)	0.0498 (14)	0.0353 (12)	0.0052 (12)	0.0150 (12)	−0.0073 (11)
N3	0.0628 (13)	0.0337 (10)	0.0640 (13)	−0.0054 (9)	0.0060 (11)	0.0002 (10)
C3	0.0553 (15)	0.0444 (13)	0.0591 (15)	0.0039 (11)	0.0200 (12)	−0.0022 (12)
C5	0.0696 (17)	0.0371 (13)	0.0588 (16)	−0.0114 (12)	0.0099 (14)	0.0049 (12)
C13	0.076 (2)	0.0492 (15)	0.087 (2)	0.0192 (14)	0.0074 (16)	−0.0042 (15)

Geometric parameters (Å, º)

O1—C6	1.220 (2)	C11—C12	1.381 (3)
N5—C6	1.370 (2)	C11—H11A	0.9300
N5—C1	1.406 (3)	C12—H12A	0.9300
N5—H5A	0.8600	C8—C9	1.375 (3)
N4—C1	1.338 (3)	C8—H8A	0.9300
N4—C5	1.349 (3)	C10—C9	1.384 (3)
C7—C12	1.387 (3)	N1—C3	1.323 (3)
C7—C8	1.394 (3)	N1—C4	1.372 (3)
C7—C6	1.484 (3)	C4—N3	1.345 (3)
C2—N2	1.368 (2)	C9—H9A	0.9300
C2—C1	1.380 (3)	N3—C5	1.323 (3)
C2—C4	1.399 (3)	C3—H3B	0.9300
N2—C3	1.342 (3)	C5—H5B	0.9300
N2—H2A	0.8600	C13—H13A	0.9600
O2—C10	1.366 (2)	C13—H13B	0.9600
O2—C13	1.418 (3)	C13—H13C	0.9600
C11—C10	1.380 (3)
C6—N5—C1	123.05 (17)	C9—C8—C7	120.7 (2)
C6—N5—H5A	118.5	C9—C8—H8A	119.7
C1—N5—H5A	118.5	C7—C8—H8A	119.7
C1—N4—C5	117.4 (2)	O2—C10—C11	124.6 (2)
C12—C7—C8	118.32 (19)	O2—C10—C9	115.5 (2)
C12—C7—C6	117.36 (18)	C11—C10—C9	119.85 (19)
C8—C7—C6	124.17 (19)	C3—N1—C4	103.52 (18)
N2—C2—C1	137.31 (19)	N3—C4—N1	125.0 (2)
N2—C2—C4	105.17 (17)	N3—C4—C2	124.4 (2)
C1—C2—C4	117.50 (19)	N1—C4—C2	110.53 (18)
C3—N2—C2	106.51 (17)	C8—C9—C10	120.2 (2)
C3—N2—H2A	126.7	C8—C9—H9A	119.9
C2—N2—H2A	126.7	C10—C9—H9A	119.9
C10—O2—C13	117.54 (19)	C5—N3—C4	112.32 (19)
O1—C6—N5	120.50 (18)	N1—C3—N2	114.3 (2)
O1—C6—C7	121.33 (18)	N1—C3—H3B	122.9
N5—C6—C7	118.10 (18)	N2—C3—H3B	122.9
N4—C1—C2	119.48 (19)	N3—C5—N4	128.8 (2)
N4—C1—N5	114.64 (18)	N3—C5—H5B	115.6
C2—C1—N5	125.87 (18)	N4—C5—H5B	115.6
C10—C11—C12	119.7 (2)	O2—C13—H13A	109.5
C10—C11—H11A	120.2	O2—C13—H13B	109.5
C12—C11—H11A	120.2	H13A—C13—H13B	109.5
C11—C12—C7	121.1 (2)	O2—C13—H13C	109.5
C11—C12—H12A	119.4	H13A—C13—H13C	109.5
C7—C12—H12A	119.4	H13B—C13—H13C	109.5
C1—C2—N2—C3	−178.7 (3)	C6—C7—C8—C9	172.9 (2)
C4—C2—N2—C3	−0.5 (2)	C13—O2—C10—C11	−4.7 (3)
C1—N5—C6—O1	6.7 (3)	C13—O2—C10—C9	176.3 (2)
C1—N5—C6—C7	−170.45 (18)	C12—C11—C10—O2	178.1 (2)
C12—C7—C6—O1	−3.9 (3)	C12—C11—C10—C9	−2.9 (3)
C8—C7—C6—O1	−179.3 (2)	C3—N1—C4—N3	175.7 (2)
C12—C7—C6—N5	173.23 (19)	C3—N1—C4—C2	−1.2 (3)
C8—C7—C6—N5	−2.2 (3)	N2—C2—C4—N3	−175.8 (2)
C5—N4—C1—C2	0.8 (3)	C1—C2—C4—N3	2.8 (3)
C5—N4—C1—N5	179.7 (2)	N2—C2—C4—N1	1.1 (2)
N2—C2—C1—N4	175.0 (2)	C1—C2—C4—N1	179.73 (19)
C4—C2—C1—N4	−3.0 (3)	C7—C8—C9—C10	−0.8 (3)
N2—C2—C1—N5	−3.7 (4)	O2—C10—C9—C8	−177.5 (2)
C4—C2—C1—N5	178.27 (19)	C11—C10—C9—C8	3.4 (3)
C6—N5—C1—N4	138.5 (2)	N1—C4—N3—C5	−176.7 (2)
C6—N5—C1—C2	−42.7 (3)	C2—C4—N3—C5	−0.2 (3)
C10—C11—C12—C7	−0.4 (3)	C4—N1—C3—N2	0.9 (3)
C8—C7—C12—C11	3.0 (3)	C2—N2—C3—N1	−0.3 (3)
C6—C7—C12—C11	−172.64 (19)	C4—N3—C5—N4	−2.4 (4)
C12—C7—C8—C9	−2.4 (3)	C1—N4—C5—N3	2.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	2.45	2.809 (2)	106
N2—H2A···N1^i	0.86	2.09	2.935 (3)	166
N5—H5A···O1^ii	0.86	2.13	2.961 (2)	163
C8—H8A···O1^ii	0.93	2.30	3.209 (3)	165

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