Supra­molecular architecture in a co-crystal of the N(7)—H tautomeric form of N⁶-benzoyl­adenine with adipic acid (1/0.5)

The supra­molecular architecture in a co-crystal of N(7)—H tautomeric form of N⁶-benzoyl­adenine-adipic acid (1/0.5) is reported. The typical C=O...π and C—H...π inter­actions are also present in this structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.045
• wR factor = 0.122
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C17 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.5 Note
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.865 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  P21/c        P21/n Note
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =         11 Note
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1B    ..  C8      ..       2.94 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           6 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

N⁶-Benzoyladenine–adipic acid (1/0.5)

Crystal data

C12H9N5O·0.5C6H10O4	F(000) = 652
Mr = 312.31	Dx = 1.424 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.1776 (4) Å	Cell parameters from 4139 reflections
b = 9.2296 (4) Å	θ = 3.3–30.1°
c = 25.7480 (15) Å	µ = 0.10 mm^−1
β = 97.117 (6)°	T = 293 K
V = 1456.76 (14) Å^3	Prism, colorless
Z = 4	0.60 × 0.60 × 0.40 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	3325 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2755 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.020
Detector resolution: 10.4933 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −8→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −11→11
Tmin = 0.756, Tmax = 1.000	l = −33→31
9480 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0541P)^2 + 0.3295P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.25 e Å^−3
3325 reflections	Δρmin = −0.22 e Å^−3
230 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0130 (18)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	0.7104 (15)	0.6427 (14)	0.1669 (8)	0.094 (4)	0.57 (3)
O1B	0.6582 (19)	0.6621 (6)	0.1877 (4)	0.054 (2)	0.43 (3)
N1	0.3308 (2)	0.27081 (12)	0.16588 (5)	0.0415 (3)
N3	0.5648 (2)	0.09828 (13)	0.21438 (5)	0.0477 (3)
N6	0.39990 (19)	0.51100 (12)	0.15270 (5)	0.0391 (3)
H6	0.2702	0.5109	0.1361	0.047*
N7	0.85319 (19)	0.42515 (12)	0.22672 (5)	0.0402 (3)
H7	0.8790	0.5157	0.2226	0.048*
N9	0.9054 (2)	0.19667 (13)	0.25397 (5)	0.0470 (3)
C2	0.3848 (3)	0.13827 (15)	0.18545 (6)	0.0468 (4)
H2	0.2811	0.0660	0.1774	0.056*
C4	0.7054 (2)	0.20808 (14)	0.22480 (5)	0.0389 (3)
C5	0.6683 (2)	0.35149 (13)	0.20707 (5)	0.0352 (3)
C6	0.4717 (2)	0.38085 (13)	0.17619 (5)	0.0347 (3)
C8	0.9855 (3)	0.32896 (15)	0.25376 (6)	0.0451 (4)
H8	1.1219	0.3535	0.2709	0.054*
C10	0.5100 (3)	0.63803 (16)	0.15283 (7)	0.0493 (4)
C11	0.4104 (2)	0.75951 (14)	0.11985 (6)	0.0412 (3)
C12	0.5550 (3)	0.86137 (17)	0.10534 (7)	0.0544 (4)
H12	0.7028	0.8527	0.1173	0.065*
C13	0.4831 (3)	0.97575 (19)	0.07333 (8)	0.0627 (5)
H13	0.5825	1.0423	0.0630	0.075*
C14	0.2660 (3)	0.99109 (19)	0.05686 (7)	0.0628 (5)
H14	0.2168	1.0681	0.0353	0.075*
C15	0.1208 (3)	0.8931 (2)	0.07213 (8)	0.0655 (5)
H15	−0.0274	0.9047	0.0611	0.079*
C16	0.1909 (3)	0.77622 (18)	0.10389 (7)	0.0538 (4)
H16	0.0908	0.7102	0.1142	0.065*
O2	0.9399 (2)	0.25032 (13)	0.10377 (6)	0.0694 (4)
H2A	1.0565	0.2620	0.1223	0.104*
O3A	1.0228 (15)	0.4644 (11)	0.0753 (5)	0.072 (2)	0.63 (3)
O3B	0.951 (3)	0.4828 (6)	0.0985 (9)	0.070 (5)	0.37 (3)
C17	0.8870 (3)	0.36824 (17)	0.07825 (6)	0.0494 (4)
C18	0.6762 (3)	0.36172 (16)	0.04285 (6)	0.0491 (4)
H18A	0.5619	0.3312	0.0631	0.059*
H18B	0.6882	0.2888	0.0162	0.059*
C19	0.6100 (3)	0.50345 (16)	0.01626 (6)	0.0494 (4)
H19A	0.6069	0.5781	0.0427	0.059*
H19B	0.7188	0.5308	−0.0060	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.047 (3)	0.085 (4)	0.138 (8)	−0.023 (2)	−0.033 (4)	0.071 (4)
O1B	0.052 (3)	0.028 (2)	0.073 (4)	−0.0097 (15)	−0.024 (2)	0.011 (2)
N1	0.0423 (6)	0.0333 (6)	0.0467 (7)	−0.0045 (5)	−0.0037 (5)	0.0046 (5)
N3	0.0559 (8)	0.0299 (6)	0.0536 (7)	−0.0047 (5)	−0.0074 (6)	0.0067 (5)
N6	0.0365 (6)	0.0308 (6)	0.0470 (6)	0.0002 (4)	−0.0071 (5)	0.0062 (5)
N7	0.0399 (6)	0.0269 (5)	0.0503 (7)	0.0015 (5)	−0.0079 (5)	0.0000 (5)
N9	0.0495 (7)	0.0310 (6)	0.0561 (7)	0.0051 (5)	−0.0108 (6)	0.0036 (5)
C2	0.0519 (9)	0.0325 (7)	0.0528 (8)	−0.0091 (6)	−0.0060 (7)	0.0062 (6)
C4	0.0444 (8)	0.0292 (6)	0.0412 (7)	0.0023 (5)	−0.0023 (6)	0.0017 (5)
C5	0.0381 (7)	0.0280 (6)	0.0383 (7)	0.0015 (5)	−0.0002 (6)	−0.0008 (5)
C6	0.0380 (7)	0.0290 (6)	0.0362 (6)	0.0006 (5)	0.0007 (6)	0.0015 (5)
C8	0.0423 (8)	0.0341 (7)	0.0550 (8)	0.0045 (6)	−0.0101 (7)	−0.0007 (6)
C10	0.0461 (8)	0.0357 (7)	0.0611 (9)	−0.0047 (6)	−0.0131 (7)	0.0124 (7)
C11	0.0472 (8)	0.0303 (6)	0.0441 (7)	0.0017 (6)	−0.0019 (6)	0.0044 (5)
C12	0.0510 (9)	0.0398 (8)	0.0710 (11)	−0.0011 (7)	0.0017 (8)	0.0131 (7)
C13	0.0716 (12)	0.0437 (9)	0.0746 (12)	0.0012 (8)	0.0155 (10)	0.0202 (8)
C14	0.0809 (13)	0.0479 (9)	0.0590 (10)	0.0163 (9)	0.0061 (9)	0.0205 (8)
C15	0.0542 (10)	0.0617 (11)	0.0771 (12)	0.0142 (9)	−0.0059 (9)	0.0204 (9)
C16	0.0464 (9)	0.0455 (8)	0.0672 (10)	0.0021 (7)	−0.0019 (8)	0.0146 (7)
O2	0.0568 (7)	0.0461 (6)	0.0963 (10)	−0.0026 (5)	−0.0264 (7)	0.0128 (6)
O3A	0.061 (3)	0.072 (2)	0.076 (4)	−0.026 (2)	−0.024 (3)	0.027 (2)
O3B	0.069 (5)	0.037 (2)	0.092 (8)	−0.006 (2)	−0.035 (5)	0.002 (2)
C17	0.0477 (9)	0.0428 (8)	0.0544 (9)	−0.0017 (7)	−0.0073 (7)	0.0029 (7)
C18	0.0472 (8)	0.0408 (8)	0.0558 (9)	−0.0017 (6)	−0.0071 (7)	−0.0016 (7)
C19	0.0481 (9)	0.0411 (8)	0.0554 (9)	−0.0023 (6)	−0.0070 (7)	0.0023 (7)

Geometric parameters (Å, º)

O1A—C10	1.247 (6)	C12—C13	1.378 (2)
O1B—C10	1.221 (6)	C12—H12	0.9300
N1—C6	1.3424 (17)	C13—C14	1.363 (3)
N1—C2	1.3489 (17)	C13—H13	0.9300
N3—C2	1.3125 (19)	C14—C15	1.365 (3)
N3—C4	1.3401 (18)	C14—H14	0.9300
N6—C10	1.3551 (18)	C15—C16	1.390 (2)
N6—C6	1.3926 (16)	C15—H15	0.9300
N6—H6	0.8600	C16—H16	0.9300
N7—C8	1.3415 (17)	O2—C17	1.2923 (18)
N7—C5	1.3712 (17)	O2—H2A	0.8200
N7—H7	0.8601	O3A—C17	1.230 (4)
N9—C8	1.3175 (19)	O3B—C17	1.223 (6)
N9—C4	1.3684 (18)	C17—C18	1.495 (2)
C2—H2	0.9300	C18—C19	1.509 (2)
C4—C5	1.4096 (17)	C18—H18A	0.9700
C5—C6	1.3931 (18)	C18—H18B	0.9700
C8—H8	0.9300	C19—C19^i	1.506 (3)
C10—C11	1.4924 (18)	C19—H19A	0.9700
C11—C16	1.376 (2)	C19—H19B	0.9700
C11—C12	1.380 (2)
C6—N1—C2	119.23 (11)	C13—C12—H12	119.6
C2—N3—C4	112.56 (12)	C11—C12—H12	119.6
C10—N6—C6	127.77 (11)	C14—C13—C12	119.81 (17)
C10—N6—H6	116.0	C14—C13—H13	120.1
C6—N6—H6	116.2	C12—C13—H13	120.1
C8—N7—C5	106.82 (11)	C13—C14—C15	119.86 (15)
C8—N7—H7	126.7	C13—C14—H14	120.1
C5—N7—H7	126.5	C15—C14—H14	120.1
C8—N9—C4	103.90 (11)	C14—C15—C16	121.01 (16)
N3—C2—N1	128.29 (13)	C14—C15—H15	119.5
N3—C2—H2	115.9	C16—C15—H15	119.5
N1—C2—H2	115.9	C11—C16—C15	119.12 (16)
N3—C4—N9	124.79 (12)	C11—C16—H16	120.4
N3—C4—C5	124.74 (12)	C15—C16—H16	120.4
N9—C4—C5	110.47 (12)	C17—O2—H2A	109.5
N7—C5—C6	137.86 (12)	O3B—C17—O2	117.6 (6)
N7—C5—C4	104.56 (11)	O3A—C17—O2	120.5 (3)
C6—C5—C4	117.57 (12)	O3B—C17—C18	120.5 (3)
N1—C6—N6	113.77 (11)	O3A—C17—C18	122.7 (2)
N1—C6—C5	117.61 (11)	O2—C17—C18	114.98 (13)
N6—C6—C5	128.60 (12)	C17—C18—C19	114.09 (13)
N9—C8—N7	114.25 (12)	C17—C18—H18A	108.7
N9—C8—H8	122.9	C19—C18—H18A	108.7
N7—C8—H8	122.9	C17—C18—H18B	108.7
O1B—C10—N6	119.4 (5)	C19—C18—H18B	108.7
O1A—C10—N6	120.7 (5)	H18A—C18—H18B	107.6
O1B—C10—C11	120.0 (3)	C19^i—C19—C18	112.99 (16)
O1A—C10—C11	117.6 (3)	C19^i—C19—H19A	109.0
N6—C10—C11	118.50 (12)	C18—C19—H19A	109.0
C16—C11—C12	119.33 (13)	C19^i—C19—H19B	109.0
C16—C11—C10	125.15 (14)	C18—C19—H19B	109.0
C12—C11—C10	115.52 (13)	H19A—C19—H19B	107.8
C13—C12—C11	120.82 (16)
C4—N3—C2—N1	0.6 (3)	C6—N6—C10—O1B	−23.5 (8)
C6—N1—C2—N3	−0.5 (3)	C6—N6—C10—O1A	13.7 (14)
C2—N3—C4—N9	−179.85 (15)	C6—N6—C10—C11	173.08 (14)
C2—N3—C4—C5	−0.1 (2)	O1B—C10—C11—C16	−138.8 (8)
C8—N9—C4—N3	179.82 (16)	O1A—C10—C11—C16	−175.5 (14)
C8—N9—C4—C5	0.06 (18)	N6—C10—C11—C16	24.5 (3)
C8—N7—C5—C6	−179.15 (18)	O1B—C10—C11—C12	40.7 (9)
C8—N7—C5—C4	−0.01 (16)	O1A—C10—C11—C12	4.0 (14)
N3—C4—C5—N7	−179.79 (15)	N6—C10—C11—C12	−156.02 (16)
N9—C4—C5—N7	−0.03 (17)	C16—C11—C12—C13	−2.8 (3)
N3—C4—C5—C6	−0.4 (2)	C10—C11—C12—C13	177.68 (17)
N9—C4—C5—C6	179.31 (13)	C11—C12—C13—C14	1.8 (3)
C2—N1—C6—N6	178.40 (13)	C12—C13—C14—C15	0.0 (3)
C2—N1—C6—C5	−0.2 (2)	C13—C14—C15—C16	−0.7 (3)
C10—N6—C6—N1	−175.34 (15)	C12—C11—C16—C15	2.0 (3)
C10—N6—C6—C5	3.0 (3)	C10—C11—C16—C15	−178.52 (16)
N7—C5—C6—N1	179.62 (16)	C14—C15—C16—C11	−0.3 (3)
C4—C5—C6—N1	0.6 (2)	O3B—C17—C18—C19	26.0 (16)
N7—C5—C6—N6	1.3 (3)	O3A—C17—C18—C19	−19.2 (10)
C4—C5—C6—N6	−177.74 (14)	O2—C17—C18—C19	176.05 (16)
C4—N9—C8—N7	−0.08 (19)	C17—C18—C19—C19^i	−176.11 (18)
C5—N7—C8—N9	0.06 (19)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C11–C16 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1^ii	0.82	1.92	2.7327 (19)	175
N6—H6···O3A^iii	0.86	2.09	2.904 (11)	157
N7—H7···O1A	0.86	2.04	2.616 (16)	124
N7—H7···N9^iv	0.86	2.17	2.9271 (17)	146
C19—H19B···O3A^v	0.97	2.54	3.481 (11)	164
C2—H2···Cg3^vi	0.93	2.94	3.4611 (16)	117

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