4,5-Bis(1H-imidazol-1-ylmeth-yl)acridine monohydrate.

In the title compound, C(21)H(17)N(5)·H(2)O, the dihedral angles between the acridine ring system and the imidazole rings are 78.8 (1) and 71.2 (1)°. The crystal packing is stabilized by O-H⋯N, C-H⋯O, C-H⋯π and π-π inter-actions [centroid-centroid separations = 3.732 (1) and 3.569 (1) Å].

Related literature

For the biological activity of acridines, see: Talacki et al. (1974 ▶); Achenson (1956 ▶); Prasad Krishna et al. (1984 ▶); Asthana et al. (1991 ▶). For their anti­protozoal activity, see: Karolak-Wojciechowska et al. (1996 ▶). For the ability of acridine to inter­calate between the base-pairs of DNA, see: Neidle (1979 ▶); Fan et al. (1997 ▶). For acridine compounds in the treatment of Alzheimer’s disease, see: Bandoli et al. (1994 ▶). For their toxicity, see: Di Giorgio et al. (2005 ▶).

Experimental

Crystal data

C21H17N5·H2O

M = 357.41

Monoclinic,

a = 14.3359 (6) Å

b = 6.9132 (3) Å

c = 17.7458 (8) Å

β = 92.895 (3)°

V = 1756.49 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.984

19520 measured reflections

4286 independent reflections

2652 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.145

S = 1.06

4286 reflections

252 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903267X/bt5021sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903267X/bt5021Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H17N5·H2O	F(000) = 752
Mr = 357.41	Dx = 1.352 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4286 reflections
a = 14.3359 (6) Å	θ = 1.8–28.1°
b = 6.9132 (3) Å	µ = 0.09 mm−1
c = 17.7458 (8) Å	T = 293 K
β = 92.895 (3)°	Block, white crystalline
V = 1756.49 (13) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4286 independent reflections
Radiation source: fine-focus sealed tube	2652 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 28.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.978, Tmax = 0.984	k = −9→8
19520 measured reflections	l = −23→23

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.3961P] where P = (Fo2 + 2Fc2)/3
4286 reflections	(Δ/σ)max < 0.001
252 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.31970 (12)	0.7854 (2)	−0.06027 (9)	0.0394 (4)
C2	0.22370 (12)	0.8010 (3)	−0.08514 (10)	0.0463 (4)
C3	0.20069 (15)	0.8387 (3)	−0.15855 (12)	0.0618 (5)
H3	0.1382	0.8558	−0.1737	0.074*
C4	0.26910 (17)	0.8528 (4)	−0.21250 (12)	0.0715 (6)
H4	0.2513	0.8793	−0.2626	0.086*
C5	0.35988 (16)	0.8283 (3)	−0.19224 (11)	0.0609 (5)
H5	0.4041	0.8324	−0.2288	0.073*
C6	0.38899 (13)	0.7960 (3)	−0.11539 (10)	0.0446 (4)
C7	0.48111 (13)	0.7751 (3)	−0.09095 (10)	0.0466 (4)
H7	0.5274	0.7779	−0.1258	0.056*
C8	0.50554 (12)	0.7500 (2)	−0.01541 (10)	0.0414 (4)
C9	0.59945 (12)	0.7289 (3)	0.01289 (12)	0.0509 (5)
H9	0.6476	0.7313	−0.0203	0.061*
C10	0.61933 (13)	0.7056 (3)	0.08691 (12)	0.0570 (5)
H10	0.6811	0.6912	0.1048	0.068*
C11	0.54661 (13)	0.7027 (3)	0.13806 (11)	0.0522 (5)
H11	0.5617	0.6857	0.1892	0.063*
C12	0.45576 (12)	0.7241 (2)	0.11476 (10)	0.0412 (4)
C13	0.43189 (11)	0.7464 (2)	0.03633 (9)	0.0374 (4)
C14	0.14924 (12)	0.7687 (3)	−0.03008 (11)	0.0490 (4)
H14A	0.1671	0.8318	0.0173	0.059*
H14B	0.0912	0.8261	−0.0496	0.059*
C15	0.10166 (15)	0.4321 (3)	−0.06850 (13)	0.0663 (6)
H15	0.0865	0.4554	−0.1193	0.080*
C16	0.09479 (17)	0.2638 (3)	−0.03245 (16)	0.0750 (7)
H16	0.0727	0.1496	−0.0545	0.090*
C18	0.38042 (13)	0.7272 (3)	0.17082 (10)	0.0465 (4)
H18A	0.3235	0.6737	0.1474	0.056*
H18B	0.3992	0.6459	0.2135	0.056*
C19	0.30224 (12)	1.0562 (3)	0.16560 (11)	0.0497 (5)
H19	0.2643	1.0415	0.1219	0.060*
C20	0.30963 (14)	1.2133 (3)	0.20991 (12)	0.0584 (5)
H20	0.2765	1.3275	0.2013	0.070*
C21	0.40165 (14)	1.0055 (3)	0.25943 (10)	0.0554 (5)
H21	0.4454	0.9443	0.2917	0.067*
N1	0.34184 (9)	0.76245 (19)	0.01343 (8)	0.0385 (3)
N2	0.13497 (9)	0.5626 (2)	−0.01681 (8)	0.0446 (4)
N3	0.12452 (15)	0.2830 (3)	0.04082 (14)	0.0815 (6)
N4	0.36165 (9)	0.9226 (2)	0.19781 (8)	0.0427 (4)
N5	0.37208 (13)	1.1834 (3)	0.26923 (10)	0.0658 (5)
O1	0.04120 (12)	0.0382 (3)	0.15544 (11)	0.0766 (5)
C17	0.14712 (15)	0.4659 (4)	0.04758 (12)	0.0668 (6)
H17	0.1693	0.5221	0.0926	0.080*
H1A	0.074 (2)	0.096 (5)	0.120 (2)	0.138 (14)*
H1B	0.066 (2)	−0.070 (4)	0.1662 (16)	0.099 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0481 (9)	0.0282 (9)	0.0424 (9)	−0.0013 (7)	0.0082 (7)	0.0005 (7)
C2	0.0493 (10)	0.0365 (10)	0.0527 (11)	−0.0003 (7)	0.0009 (8)	0.0019 (8)
C3	0.0616 (12)	0.0634 (14)	0.0593 (12)	−0.0044 (10)	−0.0090 (10)	0.0072 (10)
C4	0.0830 (16)	0.0837 (18)	0.0469 (12)	−0.0154 (13)	−0.0069 (11)	0.0117 (11)
C5	0.0765 (14)	0.0628 (14)	0.0444 (11)	−0.0136 (11)	0.0120 (10)	0.0034 (9)
C6	0.0534 (10)	0.0353 (10)	0.0459 (10)	−0.0060 (7)	0.0119 (8)	−0.0001 (7)
C7	0.0533 (10)	0.0383 (10)	0.0501 (10)	−0.0047 (8)	0.0206 (8)	−0.0025 (8)
C8	0.0435 (9)	0.0277 (9)	0.0539 (10)	−0.0006 (7)	0.0115 (7)	−0.0023 (7)
C9	0.0434 (9)	0.0424 (11)	0.0681 (13)	0.0009 (8)	0.0150 (8)	−0.0049 (9)
C10	0.0434 (10)	0.0515 (13)	0.0756 (14)	0.0053 (8)	−0.0005 (9)	−0.0052 (10)
C11	0.0560 (11)	0.0450 (12)	0.0548 (11)	0.0033 (8)	−0.0039 (9)	−0.0028 (9)
C12	0.0468 (9)	0.0302 (9)	0.0469 (10)	0.0003 (7)	0.0044 (7)	−0.0014 (7)
C13	0.0419 (9)	0.0255 (8)	0.0456 (9)	0.0006 (6)	0.0082 (7)	−0.0013 (7)
C14	0.0443 (9)	0.0406 (11)	0.0623 (12)	0.0026 (8)	0.0027 (8)	−0.0001 (9)
C15	0.0788 (14)	0.0549 (14)	0.0635 (13)	−0.0027 (11)	−0.0115 (11)	−0.0049 (11)
C16	0.0743 (15)	0.0424 (13)	0.108 (2)	−0.0039 (10)	0.0035 (14)	−0.0016 (13)
C18	0.0569 (10)	0.0406 (11)	0.0423 (9)	−0.0052 (8)	0.0057 (8)	0.0042 (8)
C19	0.0440 (9)	0.0541 (12)	0.0519 (10)	0.0030 (8)	0.0122 (8)	0.0075 (9)
C20	0.0586 (12)	0.0549 (13)	0.0642 (13)	0.0068 (9)	0.0276 (10)	0.0016 (10)
C21	0.0568 (11)	0.0655 (14)	0.0445 (10)	−0.0020 (10)	0.0071 (8)	−0.0060 (9)
N1	0.0420 (7)	0.0303 (8)	0.0440 (8)	0.0003 (5)	0.0090 (6)	−0.0001 (6)
N2	0.0398 (7)	0.0426 (9)	0.0516 (9)	0.0010 (6)	0.0040 (6)	0.0018 (7)
N3	0.0780 (13)	0.0672 (15)	0.0993 (17)	−0.0087 (10)	0.0051 (12)	0.0298 (12)
N4	0.0448 (8)	0.0454 (9)	0.0388 (7)	−0.0028 (6)	0.0111 (6)	0.0010 (6)
N5	0.0769 (12)	0.0624 (13)	0.0598 (11)	−0.0014 (9)	0.0203 (9)	−0.0158 (9)
O1	0.0682 (10)	0.0828 (14)	0.0784 (12)	0.0017 (10)	0.0003 (9)	0.0099 (10)
C17	0.0725 (14)	0.0716 (17)	0.0562 (12)	−0.0135 (12)	0.0012 (10)	0.0141 (11)

C1—N1	1.340 (2)	C14—N2	1.460 (2)
C1—C2	1.428 (2)	C14—H14A	0.9700
C1—C6	1.431 (2)	C14—H14B	0.9700
C2—C3	1.353 (3)	C15—C16	1.334 (3)
C2—C14	1.500 (2)	C15—N2	1.356 (3)
C3—C4	1.408 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—N3	1.354 (3)
C4—C5	1.343 (3)	C16—H16	0.9300
C4—H4	0.9300	C18—N4	1.462 (2)
C5—C6	1.423 (3)	C18—H18A	0.9700
C5—H5	0.9300	C18—H18B	0.9700
C6—C7	1.377 (3)	C19—C20	1.342 (3)
C7—C8	1.379 (3)	C19—N4	1.362 (2)
C7—H7	0.9300	C19—H19	0.9300
C8—C9	1.421 (3)	C20—N5	1.363 (3)
C8—C13	1.434 (2)	C20—H20	0.9300
C9—C10	1.340 (3)	C21—N5	1.315 (3)
C9—H9	0.9300	C21—N4	1.338 (2)
C10—C11	1.416 (3)	C21—H21	0.9300
C10—H10	0.9300	N2—C17	1.327 (2)
C11—C12	1.355 (2)	N3—C17	1.310 (3)
C11—H11	0.9300	O1—H1A	0.91 (4)
C12—C13	1.425 (2)	O1—H1B	0.85 (3)
C12—C18	1.505 (2)	C17—H17	0.9300
C13—N1	1.338 (2)
N1—C1—C2	119.20 (15)	N2—C14—H14A	109.4
N1—C1—C6	122.36 (15)	C2—C14—H14A	109.4
C2—C1—C6	118.44 (16)	N2—C14—H14B	109.4
C3—C2—C1	119.77 (17)	C2—C14—H14B	109.4
C3—C2—C14	120.60 (17)	H14A—C14—H14B	108.0
C1—C2—C14	119.60 (16)	C16—C15—N2	106.7 (2)
C2—C3—C4	121.58 (19)	C16—C15—H15	126.6
C2—C3—H3	119.2	N2—C15—H15	126.6
C4—C3—H3	119.2	C15—C16—N3	110.4 (2)
C5—C4—C3	120.52 (19)	C15—C16—H16	124.8
C5—C4—H4	119.7	N3—C16—H16	124.8
C3—C4—H4	119.7	N4—C18—C12	112.31 (14)
C4—C5—C6	120.63 (19)	N4—C18—H18A	109.1
C4—C5—H5	119.7	C12—C18—H18A	109.1
C6—C5—H5	119.7	N4—C18—H18B	109.1
C7—C6—C5	123.26 (17)	C12—C18—H18B	109.1
C7—C6—C1	117.86 (16)	H18A—C18—H18B	107.9
C5—C6—C1	118.88 (17)	C20—C19—N4	105.90 (18)
C6—C7—C8	120.78 (15)	C20—C19—H19	127.1
C6—C7—H7	119.6	N4—C19—H19	127.1
C8—C7—H7	119.6	C19—C20—N5	111.03 (19)
C7—C8—C9	123.10 (16)	C19—C20—H20	124.5
C7—C8—C13	117.74 (15)	N5—C20—H20	124.5
C9—C8—C13	119.16 (16)	N5—C21—N4	112.40 (19)
C10—C9—C8	120.65 (17)	N5—C21—H21	123.8
C10—C9—H9	119.7	N4—C21—H21	123.8
C8—C9—H9	119.7	C13—N1—C1	118.91 (14)
C9—C10—C11	120.20 (18)	C17—N2—C15	105.89 (18)
C9—C10—H10	119.9	C17—N2—C14	128.06 (17)
C11—C10—H10	119.9	C15—N2—C14	125.97 (17)
C12—C11—C10	122.02 (18)	C17—N3—C16	104.28 (19)
C12—C11—H11	119.0	C21—N4—C19	106.58 (17)
C10—C11—H11	119.0	C21—N4—C18	125.81 (16)
C11—C12—C13	119.33 (16)	C19—N4—C18	127.60 (15)
C11—C12—C18	120.72 (16)	C21—N5—C20	104.10 (17)
C13—C12—C18	119.95 (15)	H1A—O1—H1B	109 (3)
N1—C13—C12	119.07 (14)	N3—C17—N2	112.7 (2)
N1—C13—C8	122.30 (15)	N3—C17—H17	123.6
C12—C13—C8	118.62 (15)	N2—C17—H17	123.6
N2—C14—C2	111.13 (14)
N1—C1—C2—C3	175.05 (17)	C9—C8—C13—N1	−178.93 (15)
C6—C1—C2—C3	−4.7 (3)	C7—C8—C13—C12	−178.90 (15)
N1—C1—C2—C14	−7.0 (2)	C9—C8—C13—C12	0.8 (2)
C6—C1—C2—C14	173.28 (16)	C3—C2—C14—N2	99.4 (2)
C1—C2—C3—C4	3.6 (3)	C1—C2—C14—N2	−78.6 (2)
C14—C2—C3—C4	−174.4 (2)	N2—C15—C16—N3	−1.1 (3)
C2—C3—C4—C5	0.2 (4)	C11—C12—C18—N4	89.8 (2)
C3—C4—C5—C6	−2.8 (4)	C13—C12—C18—N4	−89.38 (19)
C4—C5—C6—C7	−178.2 (2)	N4—C19—C20—N5	0.1 (2)
C4—C5—C6—C1	1.5 (3)	C12—C13—N1—C1	179.31 (14)
N1—C1—C6—C7	2.2 (2)	C8—C13—N1—C1	−1.0 (2)
C2—C1—C6—C7	−178.12 (16)	C2—C1—N1—C13	179.48 (15)
N1—C1—C6—C5	−177.52 (17)	C6—C1—N1—C13	−0.8 (2)
C2—C1—C6—C5	2.2 (2)	C16—C15—N2—C17	0.5 (2)
C5—C6—C7—C8	177.98 (18)	C16—C15—N2—C14	−176.70 (17)
C1—C6—C7—C8	−1.7 (3)	C2—C14—N2—C17	118.2 (2)
C6—C7—C8—C9	−179.63 (16)	C2—C14—N2—C15	−65.3 (2)
C6—C7—C8—C13	0.0 (2)	C15—C16—N3—C17	1.3 (3)
C7—C8—C9—C10	179.76 (18)	N5—C21—N4—C19	0.1 (2)
C13—C8—C9—C10	0.1 (3)	N5—C21—N4—C18	179.16 (15)
C8—C9—C10—C11	−0.3 (3)	C20—C19—N4—C21	−0.08 (19)
C9—C10—C11—C12	−0.4 (3)	C20—C19—N4—C18	−179.16 (15)
C10—C11—C12—C13	1.3 (3)	C12—C18—N4—C21	−92.4 (2)
C10—C11—C12—C18	−177.90 (18)	C12—C18—N4—C19	86.5 (2)
C11—C12—C13—N1	178.27 (15)	N4—C21—N5—C20	0.0 (2)
C18—C12—C13—N1	−2.6 (2)	C19—C20—N5—C21	0.0 (2)
C11—C12—C13—C8	−1.4 (2)	C16—N3—C17—N2	−1.0 (3)
C18—C12—C13—C8	177.73 (15)	C15—N2—C17—N3	0.4 (3)
C7—C8—C13—N1	1.4 (2)	C14—N2—C17—N3	177.43 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O1i	0.97	2.55	3.482 (3)	162
O1—H1A···N3	0.90 (3)	2.07 (3)	2.945 (3)	166 (3)
O1—H1B···N5ii	0.85 (3)	2.21 (3)	3.030 (3)	162 (3)
C7—H7···Cg1iii	0.93	2.69	3.577 (2)	159
C20—H20···Cg1iv	0.93	2.90	3.648 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯O1i	0.97	2.55	3.482 (3)	162
O1—H1A⋯N3	0.90 (3)	2.07 (3)	2.945 (3)	166 (3)
O1—H1B⋯N5ii	0.85 (3)	2.21 (3)	3.030 (3)	162 (3)
C7—H7⋯Cg1iii	0.93	2.69	3.577 (2)	159
C20—H20⋯Cg1iv	0.93	2.90	3.648 (2)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the N4/N5/C19–C21 ring.