4,5-Bis(1H-imidazol-1-ylmeth­yl)acridine monohydrate

Thenmozhi, S.; Ranjith, S.; Raja, S.; Rajakumar, P.; SubbiahPandi, A.

doi:10.1107/S160053680903267X

organic compounds

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Volume 65| Part 9| September 2009| Page o2211

doi:10.1107/S160053680903267X

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4,5-Bis(1H-imidazol-1-ylmethyl)acridine monohydrate

S. Thenmozhi,^a S. Ranjith,^a S. Raja,^b P. Rajakumar ^b and A. SubbiahPandi ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Chennai 600 025, India
^*Correspondence e-mail: a_spandian@yahoo.com

(Received 28 July 2009; accepted 17 August 2009; online 22 August 2009)

In the title compound, C₂₁H₁₇N₅·H₂O, 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 interactions [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_r = 357.41
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.145
S = 1.06
4286 reflections
252 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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⋯Cg1^iv	0.93	2.90	3.648 (2)	139
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{3\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the N4/N5/C19–C21 ring.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Acridines are found to have a wide range of biological activities, such as mutagenic, antitumour (Talacki et al., 1974), antibacterial (Achenson, 1956), antiamoebic (Prasad Krishna et al., 1984), hypersensitive, antiinflammatory and antiimplantation (Asthana et al., 1991) activities. A drug containing the acridine moiety has been found to possess antiprotozoal activity (Karolak-Wojciechowska et al., 1996). The ability of acridine to intercalate between the base-pairs of DNA is also well known (Neidle, 1979; Fan et al., 1997). Acridine compounds are considered to be efficient drugs for the treatment of Alzheimer's disease (Bandoli et al., 1994). Acridine derivatives have been shown to exert toxicity towards Plasmodium, Trypanosoma, and Leishmania parasites (Di Giorgio et al., 2005). The imidazole group have found a wide range of applications in coordination chemistry as ligands, in medicinal chemistry and materials science. Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound has been carried out.

The two imidazole groups are almost parallel to each other, the dihedral angle between the mean planes being 39.5 (1)°; these planes are inclined at 78.9 (1)° and 71.2 (9)° with respect to the mean plane of the acridine system. The pseudo-torsion angle N2–C14···.C18–N4 [-145.8 (2)°], resulting in both imidazole group being approximately bisected by the plane of the acridine system. The acridine ring system and imidazole rings are essentially planar, with maximum deviations of 0.062 (3), 0.006 (2) and 0.001 (2) Å, for atoms C4, N3 and C19, respectively.

The crystal packing is stabilized by C–H···O, C–H···N, C–H···π (Table. 1) and π–π interactions with a Cg2···Cg2ⁱⁱ and a Cg4···Cg3^iv separation of 3.732 (1)Å and 3.569 (1) Å, respectively (Fig.2; Cg2, Cg3 and Cg4 are the centroids of the N2/N3/C15–C17 imidazole ring, N1/C1/C6/C7/C8/C13 pyridine ring and C8–C13 benzene ring, respectively, symmetry code as in Fig. 2).

Related literature top

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). Cg1 is the centroid of the N4/N5/C19–C21 ring.

Experimental top

To a solution of imidazole, in the presence of acetonitrile (50 ml) and NaOH solution (7.5 ml) was added and stirred for 10 minutes, then 4,5-bis(bromomethyl) acridine in the presence of acetonitrile(20 ml) was added at once and stirred at room temperature for 48hrs. After completion of reaction, the solvent was evaporated in vaccum and the residue was extracted with CHCl₃(300 ml). Single crystals suitable for the X-ray diffraction were obtained by slow evaporation of a solution of the title compound in methanol at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of the title compound, showing the atom-numbering scheme and intramolecular hydrogen bond. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. C–H···O, O–H···N, C–H···π and π—π interactions (dotted lines) in the title compound. Cg denotes ring centroid. [Symmetry code: (i) -1/2 - x, 1/2 + y, 1/2 - z; (ii) -x, 1 - y, -z; (iii) 1 - x, 2 - y, -z; (iv) 1 - x, 1 - y, -z; (v) 1/2 - x, 2 - y, -z]

4,5-Bis(1H-imidazol-1-ylmethyl)acridine monohydrate top

Crystal data top

C₂₁H₁₇N₅·H₂O	F(000) = 752
M_r = 357.41	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0577P)² + 0.3961P] where P = (F_o² + 2F_c²)/3
4286 reflections	(Δ/σ)_max < 0.001
252 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₁₇N₅·H₂O	V = 1756.49 (13) Å³
M_r = 357.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.3359 (6) Å	µ = 0.09 mm⁻¹
b = 6.9132 (3) Å	T = 293 K
c = 17.7458 (8) Å	0.25 × 0.22 × 0.19 mm
β = 92.895 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4286 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2652 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.984	R_int = 0.036
19520 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.19 e Å⁻³
4286 reflections	Δρ_min = −0.20 e Å⁻³
252 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg1ⁱ	0.93	2.90	3.648 (2)	139

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇N₅·H₂O
M_r	357.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.3359 (6), 6.9132 (3), 17.7458 (8)
β (°)	92.895 (3)
V (Å³)	1756.49 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.978, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	19520, 4286, 2652
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.663

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.145, 1.06
No. of reflections	4286
No. of parameters	252
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O1ⁱ	0.97	2.55	3.482 (3)	161.6
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···Cg1ⁱ	0.93	2.90	3.648 (2)	139

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

Acknowledgements

ST and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray data collection.

References

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