(E)-2-[2-(4-Chloro­benzyl­idene)hydrazin-1-yl]-4-{[3-(dimethyl­aza­nium­yl)prop­yl]amino}­quinazolin-1-ium bis­(perchlorate)

Jiang, N.; Zuo, J.; Wang, H.; Han, M.; Zhai, X.

doi:10.1107/S1600536812018272

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1557-o1558

doi:10.1107/S1600536812018272

Open

access

(E)-2-[2-(4-Chlorobenzylidene)hydrazin-1-yl]-4-{[3-(dimethylazaniumyl)propyl]amino}quinazolin-1-ium bis(perchlorate)

Nan Jiang,^a Jian Zuo,^b Haiyan Wang,^a Ming Han ^a and Xin Zhai ^a ^*

^aKey Laboratory of Original New Drug Design and Discovery of the Ministry of Education, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, People's Republic of China, and ^bKey Laboratory of Marine Chemistry Theory and Technology, Ministry of Education, College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao, Shandong 266100, People's Republic of China
^*Correspondence e-mail: leixinjia@126.com

(Received 6 March 2012; accepted 24 April 2012; online 28 April 2012)

In the title compound, C₂₀H₂₅ClN₆²⁺·2ClO₄⁻, the organic cation is roughly planar, as shown by the dihedral angle of 3.78 (3)° between the quinazoline and chlorophenyl rings. The quinazoline ring is itself approximately planar, with an average deviation of 0.018 (4) Å. The organic cation adopts an E configuration with respect to the C= N double bond of the hyrazinyl group. The (dimethylazaniumyl)propylamino side chain is disordered over two sets of sites with occupancies of 0.768 (10) and 0.232 (10). In the crystal, two cations and four anions are linked by strong N—H⋯O hydrogen bonds. Weak C—H⋯O hydrogen bonds exist among these aggregates.

Related literature

For antitumor background to the title compound, see: Abouzid & Shouman (2008 ); Zhang et al. (2008 ); An et al. (2010 ); Horiuchi et al. (2009). For the structures of closely related compounds, see: Fun et al. (2010 ); Ferreira et al. (2009 ); de Souza et al. (2010 ); Loh et al. (2011 ).

Experimental

Crystal data

C₂₀H₂₅ClN₆²⁺·2ClO₄⁻
M_r = 583.81
Triclinic, $[P \overline 1]$
a = 10.4533 (18) Å
b = 10.5018 (18) Å
c = 12.626 (2) Å
α = 104.745 (9)°
β = 91.146 (10)°
γ = 96.21 (1)°
V = 1330.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.18 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.907, T_max = 0.932
12435 measured reflections
4889 independent reflections
3979 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.219
S = 1.09
4889 reflections
371 parameters
62 restraints
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.91	2.19	2.990 (5)	147
N5—H5C⋯O2	0.86	2.11	2.922 (4)	157
N4—H4C⋯O1ⁱ	0.86	2.14	2.964 (4)	160
N2—H2D⋯O7	0.86	2.10	2.873 (5)	149
C19—H19⋯O2ⁱⁱ	0.93	2.48	3.316 (5)	150
C1—H1D⋯O6ⁱⁱⁱ	0.96	2.56	3.445 (8)	153
C1—H1C⋯O6^iv	0.96	2.62	3.555 (10)	166
Symmetry codes: (i) -x, -y+1, -z; (ii) -x, -y+2, -z; (iii) x, y+1, z; (iv) -x+1, -y+1, -z+1.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812018272/im2363sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812018272/im2363Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812018272/im2363Isup3.cml

checkCIF report

Comment top

The target compound was designed and synthesized as part of on-going studies aimed at developing antitumor agents based on 4-aminoquinazoline and 4-aminoquinoline nuclei. These have aroused increasing attentions for excellent antitumor potency in recent years, such as gefitinib, the traditional immunostimulatory agents CQ and their derivatives (Abouzid et al., 2008; Zhang et al., 2008; An et al., 2010). With the aim to improve the electron affinity and better biological interactions, a hydrazone fragment was introduced (Horiuchi et al., 2009).

The crystal structure of the title compound is given in Fig. 1. The quinazoline ring is approximately planar, with an average deviation of 0.018 (4) Å. The dihedral angle between the quinazoline ring and the chlorophenyl ring is 3.78 (3) °. The (dimethylazaniumyl)propylamino side chain of the compound is disordered over two sites with occupancies of 0.768 (10) and 0.232 (10), respectively. The cationic part of the compound establishes strong N–H···O hydrogen bonds (N5—H5C–O2, N2—H2D–O7, N1—H1A–O3, N4—H4C–O1, Table 1) with the perchlorate anions. The resulting aggregates of two cations and four anions are linked by weak C–H···O hydrogen bonds (C1—H1C–O6, C1—H1D–O6, C19—H19–O2, Table 1) in the crystal structure (Fig. 2).

Related literature top

For antitumor background to the title compound, see: Abouzid & Shouman (2008); Zhang et al. (2008); An et al. (2010); Horiuchi et al. (2009). For the structures of very closely related compounds, see: Fun et al. (2010); Ferreira et al. (2009); de Souza et al. (2010); Loh et al. (2011).

Experimental top

Using 2-aminobenzoic acid and urea as the starting materials, (E)-N-(2-(2-(4-chlorobenzylidene)hydrazinyl) quinazolin-4-yl)-N',N'-dimethylpropane-1,3-diamine was prepared according to literature methods (Abouzid et al., 2008; Horiuchi et al., 2009). The compound was purified by silica gel column chromatography (CH₂Cl₂/Methanol 15:1). 70% Perchloric acid (24 mmol, 1.96 ml) was added to a solution of the compound (20 mmol, 7.7 g) in acetone (50 ml) at room temperature. Then the reaction mixture was stirred at 313 K for 3 h. After cooling to ambient temperature, the resulting precipitate was filtered and washed with acetone. The resulting solids were dissolved in methanol for 15 days to yield the title compound as colorless single crystals (70% yield).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Packing diagram of the title compound.

(E)-2-[2-(4-Chlorobenzylidene)hydrazin-1-yl]- 4-{[3-(dimethylazaniumyl)propyl]amino}quinazolin-1-ium bis(perchlorate) top

Crystal data top

C₂₀H₂₅ClN₆²⁺·2ClO₄⁻	Z = 2
M_r = 583.81	F(000) = 604
Triclinic, P1	D_x = 1.457 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.4533 (18) Å	Cell parameters from 4829 reflections
b = 10.5018 (18) Å	θ = 2.5–30.1°
c = 12.626 (2) Å	µ = 0.40 mm⁻¹
α = 104.745 (9)°	T = 293 K
β = 91.146 (10)°	Block, colorless
γ = 96.21 (1)°	0.25 × 0.23 × 0.18 mm
V = 1330.9 (4) Å³

Data collection top

Siemens SMART CCD area-detector diffractometer	4889 independent reflections
Radiation source: fine-focus sealed tube	3979 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
phi and ω scans	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.907, T_max = 0.932	k = −12→12
12435 measured reflections	l = −14→15

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.219	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1339P)² + 1.0689P] where P = (F_o² + 2F_c²)/3
4889 reflections	(Δ/σ)_max < 0.001
371 parameters	Δρ_max = 0.69 e Å⁻³
62 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

C₂₀H₂₅ClN₆²⁺·2ClO₄⁻	γ = 96.21 (1)°
M_r = 583.81	V = 1330.9 (4) Å³
Triclinic, P1	Z = 2
a = 10.4533 (18) Å	Mo Kα radiation
b = 10.5018 (18) Å	µ = 0.40 mm⁻¹
c = 12.626 (2) Å	T = 293 K
α = 104.745 (9)°	0.25 × 0.23 × 0.18 mm
β = 91.146 (10)°

Data collection top

Siemens SMART CCD area-detector diffractometer	4889 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3979 reflections with I > 2σ(I)
T_min = 0.907, T_max = 0.932	R_int = 0.023
12435 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	62 restraints
wR(F²) = 0.219	H-atom parameters constrained
S = 1.09	Δρ_max = 0.69 e Å⁻³
4889 reflections	Δρ_min = −0.92 e Å⁻³
371 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	Occ. (<1)
Cl1	0.32941 (8)	0.74253 (8)	0.10002 (7)	0.0433 (3)
Cl2	0.26374 (10)	0.25136 (12)	0.61278 (8)	0.0638 (4)
Cl3	−0.49702 (12)	0.78162 (13)	−0.25924 (10)	0.0702 (4)
N2	0.2182 (3)	0.4226 (3)	0.3840 (3)	0.0455 (7)
H2D	0.2213	0.3602	0.4166	0.055*
N3	0.1121 (3)	0.5197 (3)	0.2718 (2)	0.0391 (6)
N4	−0.0771 (3)	0.4117 (3)	0.1697 (2)	0.0380 (6)
H4C	−0.1379	0.4135	0.1234	0.046*
N5	0.0158 (3)	0.6172 (3)	0.1555 (2)	0.0399 (6)
H5C	0.0781	0.6806	0.1710	0.048*
N6	−0.0855 (3)	0.6209 (3)	0.0851 (2)	0.0369 (6)
O1	0.3001 (3)	0.6543 (3)	−0.0088 (2)	0.0553 (7)
O2	0.2245 (3)	0.8192 (3)	0.1395 (3)	0.0617 (8)
O3	0.3692 (3)	0.6777 (3)	0.1811 (2)	0.0582 (7)
O4	0.4611 (4)	0.8581 (4)	0.0865 (4)	0.1015 (14)
O5	0.1324 (4)	0.2708 (10)	0.6082 (4)	0.201 (4)
O6	0.2930 (6)	0.1273 (4)	0.6352 (4)	0.123 (2)
O7	0.3248 (4)	0.2711 (4)	0.5170 (3)	0.0731 (9)
O8	0.3333 (5)	0.3762 (5)	0.7247 (4)	0.1072 (14)
C1	0.3790 (6)	0.9314 (8)	0.3904 (6)	0.094 (3)	0.768 (10)
H1B	0.3551	0.9663	0.3306	0.141*	0.768 (10)
H1C	0.4612	0.8987	0.3783	0.141*	0.768 (10)
H1D	0.3842	1.0001	0.4576	0.141*	0.768 (10)
C2	0.1534 (15)	0.8623 (13)	0.3983 (9)	0.054 (3)	0.768 (10)
H2A	0.0894	0.7915	0.4033	0.081*	0.768 (10)
H2B	0.1373	0.8877	0.3318	0.081*	0.768 (10)
H2C	0.1493	0.9370	0.4601	0.081*	0.768 (10)
N1	0.2784 (4)	0.8189 (4)	0.3980 (3)	0.0711 (11)	0.768 (10)
H1A	0.2818	0.7500	0.3379	0.085*	0.768 (10)
C3	0.3380 (7)	0.7866 (6)	0.4925 (5)	0.071 (2)	0.768 (10)
H3A	0.3252	0.8526	0.5596	0.085*	0.768 (10)
H3B	0.4297	0.7839	0.4841	0.085*	0.768 (10)
C4	0.2729 (9)	0.6522 (6)	0.4957 (5)	0.079 (3)	0.768 (10)
H4A	0.1807	0.6504	0.4836	0.095*	0.768 (10)
H4B	0.2881	0.6397	0.5683	0.095*	0.768 (10)
C5	0.3222 (4)	0.5303 (4)	0.4057 (4)	0.0635 (12)	0.768 (10)
H5A	0.3423	0.5563	0.3390	0.076*	0.768 (10)
H5B	0.3990	0.5033	0.4340	0.076*	0.768 (10)
C1'	0.4014 (16)	0.885 (3)	0.438 (2)	0.081 (7)	0.232 (10)
H1'B	0.4612	0.8206	0.4339	0.121*	0.232 (10)
H1'C	0.3972	0.9346	0.5124	0.121*	0.232 (10)
H1'D	0.4297	0.9437	0.3936	0.121*	0.232 (10)
C2'	0.156 (4)	0.896 (4)	0.397 (4)	0.059 (11)	0.232 (10)
H2'A	0.1676	0.9518	0.3478	0.089*	0.232 (10)
H2'B	0.1452	0.9492	0.4697	0.089*	0.232 (10)
H2'C	0.0805	0.8331	0.3734	0.089*	0.232 (10)
N1'	0.2784 (4)	0.8189 (4)	0.3980 (3)	0.0711 (11)	0.232 (10)
H1'A	0.2844	0.7628	0.3307	0.085*	0.232 (10)
C3'	0.2400 (10)	0.7379 (10)	0.4811 (8)	0.027 (4)	0.232 (10)
H3'A	0.2259	0.7983	0.5508	0.032*	0.232 (10)
H3'B	0.1594	0.6825	0.4552	0.032*	0.232 (10)
C4'	0.3425 (12)	0.6497 (11)	0.4986 (10)	0.033 (4)	0.232 (10)
H4'A	0.4283	0.6954	0.4992	0.040*	0.232 (10)
H4'B	0.3320	0.6261	0.5676	0.040*	0.232 (10)
C5'	0.3222 (4)	0.5303 (4)	0.4057 (4)	0.0635 (12)	0.232 (10)
H5'A	0.3229	0.5634	0.3407	0.076*	0.232 (10)
H5'B	0.4003	0.4881	0.4056	0.076*	0.232 (10)
C6	0.1190 (3)	0.4168 (3)	0.3162 (3)	0.0377 (7)
C7	0.0215 (3)	0.3013 (3)	0.2901 (3)	0.0377 (7)
C8	0.0235 (4)	0.1903 (4)	0.3319 (3)	0.0476 (8)
H8	0.0881	0.1891	0.3833	0.057*
C9	−0.0688 (4)	0.0830 (4)	0.2980 (3)	0.0523 (9)
H9	−0.0663	0.0093	0.3258	0.063*
C10	−0.1655 (4)	0.0850 (4)	0.2224 (3)	0.0535 (9)
H10	−0.2279	0.0121	0.1998	0.064*
C11	−0.1714 (4)	0.1935 (4)	0.1798 (3)	0.0491 (9)
H11	−0.2375	0.1940	0.1297	0.059*
C12	−0.0763 (3)	0.3026 (3)	0.2132 (3)	0.0384 (7)
C13	0.0161 (3)	0.5139 (3)	0.1994 (3)	0.0353 (7)
C14	−0.0831 (3)	0.7243 (3)	0.0498 (3)	0.0398 (7)
H14	−0.0154	0.7918	0.0722	0.048*
C15	−0.1847 (3)	0.7380 (3)	−0.0249 (3)	0.0376 (7)
C16	−0.2904 (3)	0.6397 (3)	−0.0569 (3)	0.0425 (8)
H16	−0.2963	0.5654	−0.0292	0.051*
C17	−0.3850 (4)	0.6532 (4)	−0.1289 (3)	0.0478 (9)
H17	−0.4547	0.5880	−0.1506	0.057*
C18	−0.3756 (3)	0.7649 (4)	−0.1690 (3)	0.0440 (8)
C19	−0.2739 (4)	0.8635 (4)	−0.1393 (3)	0.0464 (8)
H19	−0.2689	0.9374	−0.1676	0.056*
C20	−0.1798 (3)	0.8500 (3)	−0.0664 (3)	0.0437 (8)
H20	−0.1113	0.9168	−0.0442	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0423 (5)	0.0379 (5)	0.0468 (5)	−0.0048 (3)	−0.0039 (3)	0.0099 (4)
Cl2	0.0543 (6)	0.0819 (8)	0.0474 (6)	−0.0141 (5)	−0.0011 (4)	0.0116 (5)
Cl3	0.0688 (7)	0.0759 (8)	0.0666 (7)	0.0096 (6)	−0.0302 (5)	0.0216 (6)
N2	0.0436 (16)	0.0429 (16)	0.0513 (17)	0.0030 (12)	−0.0128 (13)	0.0165 (13)
N3	0.0363 (14)	0.0390 (15)	0.0406 (15)	0.0044 (11)	−0.0049 (11)	0.0086 (12)
N4	0.0353 (14)	0.0420 (15)	0.0369 (14)	0.0026 (11)	−0.0058 (11)	0.0119 (12)
N5	0.0338 (14)	0.0432 (16)	0.0436 (15)	0.0020 (11)	−0.0071 (11)	0.0144 (12)
N6	0.0329 (13)	0.0410 (15)	0.0375 (14)	0.0041 (11)	−0.0051 (11)	0.0119 (12)
O1	0.0659 (17)	0.0486 (15)	0.0455 (14)	−0.0049 (13)	−0.0153 (12)	0.0072 (12)
O2	0.0433 (15)	0.0480 (16)	0.090 (2)	−0.0004 (12)	0.0120 (14)	0.0124 (15)
O3	0.0685 (18)	0.0532 (16)	0.0528 (16)	−0.0003 (13)	−0.0138 (13)	0.0178 (13)
O4	0.081 (3)	0.082 (3)	0.126 (3)	−0.016 (2)	0.024 (2)	0.008 (2)
O5	0.042 (2)	0.408 (12)	0.098 (4)	0.007 (4)	−0.017 (2)	−0.026 (5)
O6	0.222 (6)	0.058 (2)	0.084 (3)	−0.029 (3)	0.009 (3)	0.029 (2)
O7	0.092 (2)	0.086 (2)	0.0534 (17)	0.0278 (19)	0.0155 (16)	0.0313 (16)
O8	0.091 (3)	0.111 (3)	0.102 (3)	0.006 (2)	−0.008 (2)	−0.001 (3)
C1	0.047 (3)	0.133 (7)	0.067 (4)	0.006 (4)	−0.015 (3)	−0.034 (4)
C2	0.064 (5)	0.042 (8)	0.051 (4)	0.011 (5)	−0.003 (3)	0.002 (4)
N1	0.096 (3)	0.074 (2)	0.0416 (18)	0.044 (2)	−0.0082 (17)	−0.0013 (16)
C3	0.078 (5)	0.075 (4)	0.054 (3)	0.008 (4)	−0.011 (3)	0.006 (3)
C4	0.095 (6)	0.089 (5)	0.037 (3)	−0.045 (5)	−0.012 (3)	0.011 (3)
C5	0.064 (3)	0.056 (2)	0.072 (3)	−0.012 (2)	−0.034 (2)	0.031 (2)
C1'	0.094 (11)	0.083 (10)	0.079 (10)	0.007 (8)	−0.001 (8)	0.048 (9)
C2'	0.037 (11)	0.009 (12)	0.12 (2)	0.001 (8)	0.015 (11)	0.005 (10)
N1'	0.096 (3)	0.074 (2)	0.0416 (18)	0.044 (2)	−0.0082 (17)	−0.0013 (16)
C3'	0.026 (7)	0.016 (6)	0.029 (6)	−0.008 (5)	−0.003 (5)	−0.009 (5)
C4'	0.016 (6)	0.052 (7)	0.028 (6)	−0.018 (5)	−0.016 (5)	0.013 (5)
C5'	0.064 (3)	0.056 (2)	0.072 (3)	−0.012 (2)	−0.034 (2)	0.031 (2)
C6	0.0398 (17)	0.0392 (17)	0.0345 (16)	0.0077 (13)	−0.0010 (13)	0.0095 (13)
C7	0.0377 (17)	0.0405 (18)	0.0348 (16)	0.0041 (13)	−0.0003 (13)	0.0100 (13)
C8	0.050 (2)	0.049 (2)	0.049 (2)	0.0068 (16)	−0.0018 (16)	0.0198 (16)
C9	0.055 (2)	0.048 (2)	0.057 (2)	0.0001 (17)	0.0010 (18)	0.0220 (18)
C10	0.054 (2)	0.046 (2)	0.059 (2)	−0.0074 (17)	−0.0009 (18)	0.0162 (18)
C11	0.0455 (19)	0.054 (2)	0.047 (2)	−0.0047 (16)	−0.0081 (15)	0.0169 (17)
C12	0.0374 (16)	0.0400 (18)	0.0375 (17)	0.0020 (13)	0.0027 (13)	0.0102 (14)
C13	0.0353 (16)	0.0379 (17)	0.0333 (15)	0.0085 (13)	0.0006 (12)	0.0088 (13)
C14	0.0372 (17)	0.0385 (18)	0.0428 (18)	0.0018 (13)	−0.0055 (13)	0.0102 (14)
C15	0.0394 (17)	0.0347 (17)	0.0379 (16)	0.0065 (13)	−0.0014 (13)	0.0073 (13)
C16	0.0475 (19)	0.0337 (17)	0.0449 (18)	0.0031 (14)	−0.0054 (15)	0.0091 (14)
C17	0.049 (2)	0.0392 (19)	0.049 (2)	0.0010 (15)	−0.0108 (16)	0.0037 (15)
C18	0.0437 (18)	0.051 (2)	0.0357 (17)	0.0128 (15)	−0.0069 (14)	0.0059 (15)
C19	0.052 (2)	0.0432 (19)	0.050 (2)	0.0102 (16)	−0.0016 (16)	0.0206 (16)
C20	0.0400 (18)	0.0367 (18)	0.056 (2)	0.0017 (14)	−0.0035 (15)	0.0155 (15)

Geometric parameters (Å, º) top

Cl1—O3	1.444 (3)	C5—H5A	0.9700
Cl1—O2	1.452 (3)	C5—H5B	0.9700
Cl1—O1	1.454 (3)	C1'—H1'B	0.9600
Cl1—O4	1.775 (4)	C1'—H1'C	0.9600
Cl2—O5	1.412 (5)	C1'—H1'D	0.9600
Cl2—O7	1.430 (3)	C2'—H2'A	0.9600
Cl2—O6	1.464 (5)	C2'—H2'B	0.9600
Cl2—O8	1.747 (5)	C2'—H2'C	0.9600
Cl3—C18	1.741 (4)	C3'—C4'	1.538 (10)
N2—C6	1.318 (4)	C3'—H3'A	0.9700
N2—C5	1.450 (5)	C3'—H3'B	0.9700
N2—H2D	0.8600	C4'—H4'A	0.9700
N3—C13	1.330 (4)	C4'—H4'B	0.9700
N3—C6	1.346 (4)	C6—C7	1.461 (5)
N4—C13	1.341 (4)	C7—C12	1.398 (5)
N4—C12	1.392 (4)	C7—C8	1.400 (5)
N4—H4C	0.8600	C8—C9	1.374 (5)
N5—C13	1.338 (4)	C8—H8	0.9300
N5—N6	1.379 (4)	C9—C10	1.382 (6)
N5—H5C	0.8600	C9—H9	0.9300
N6—C14	1.272 (4)	C10—C11	1.384 (6)
C1—N1	1.517 (7)	C10—H10	0.9300
C1—H1B	0.9600	C11—C12	1.404 (5)
C1—H1C	0.9600	C11—H11	0.9300
C1—H1D	0.9600	C14—C15	1.450 (5)
C2—N1	1.430 (16)	C14—H14	0.9300
C2—H2A	0.9600	C15—C20	1.400 (5)
C2—H2B	0.9600	C15—C16	1.404 (5)
C2—H2C	0.9600	C16—C17	1.372 (5)
N1—C3	1.465 (6)	C16—H16	0.9300
N1—H1A	0.9100	C17—C18	1.386 (5)
C3—C4	1.510 (7)	C17—H17	0.9300
C3—H3A	0.9700	C18—C19	1.375 (5)
C3—H3B	0.9700	C19—C20	1.378 (5)
C4—C5	1.620 (7)	C19—H19	0.9300
C4—H4A	0.9700	C20—H20	0.9300
C4—H4B	0.9700

O3—Cl1—O2	110.00 (19)	H5A—C5—H5B	108.6
O3—Cl1—O1	114.28 (17)	H1'B—C1'—H1'C	109.5
O2—Cl1—O1	112.44 (19)	H1'B—C1'—H1'D	109.5
O3—Cl1—O4	107.1 (2)	H1'C—C1'—H1'D	109.5
O2—Cl1—O4	106.45 (18)	H2'A—C2'—H2'B	109.5
O1—Cl1—O4	106.02 (19)	H2'A—C2'—H2'C	109.5
O5—Cl2—O7	110.7 (3)	H2'B—C2'—H2'C	109.5
O5—Cl2—O6	116.7 (5)	C4'—C3'—H3'A	109.0
O7—Cl2—O6	110.9 (3)	C4'—C3'—H3'B	109.0
O5—Cl2—O8	105.3 (3)	H3'A—C3'—H3'B	107.8
O7—Cl2—O8	107.5 (2)	C3'—C4'—H4'A	110.6
O6—Cl2—O8	105.0 (3)	C3'—C4'—H4'B	110.6
C6—N2—C5	122.3 (3)	H4'A—C4'—H4'B	108.7
C6—N2—H2D	118.8	N2—C6—N3	117.7 (3)
C5—N2—H2D	118.8	N2—C6—C7	120.5 (3)
C13—N3—C6	119.0 (3)	N3—C6—C7	121.8 (3)
C13—N4—C12	120.5 (3)	C12—C7—C8	119.3 (3)
C13—N4—H4C	119.7	C12—C7—C6	115.8 (3)
C12—N4—H4C	119.7	C8—C7—C6	124.8 (3)
C13—N5—N6	119.2 (3)	C9—C8—C7	120.7 (4)
C13—N5—H5C	120.4	C9—C8—H8	119.6
N6—N5—H5C	120.4	C7—C8—H8	119.6
C14—N6—N5	116.2 (3)	C8—C9—C10	119.7 (4)
N1—C1—H1B	109.5	C8—C9—H9	120.1
N1—C1—H1C	109.5	C10—C9—H9	120.1
H1B—C1—H1C	109.5	C9—C10—C11	121.2 (4)
N1—C1—H1D	109.5	C9—C10—H10	119.4
H1B—C1—H1D	109.5	C11—C10—H10	119.4
H1C—C1—H1D	109.5	C10—C11—C12	119.2 (4)
N1—C2—H2A	109.5	C10—C11—H11	120.4
N1—C2—H2B	109.5	C12—C11—H11	120.4
H2A—C2—H2B	109.5	N4—C12—C7	119.5 (3)
N1—C2—H2C	109.5	N4—C12—C11	120.8 (3)
H2A—C2—H2C	109.5	C7—C12—C11	119.8 (3)
H2B—C2—H2C	109.5	N3—C13—N5	116.5 (3)
C2—N1—C3	123.2 (6)	N3—C13—N4	123.4 (3)
C2—N1—C1	109.2 (6)	N5—C13—N4	120.1 (3)
C3—N1—C1	97.5 (5)	N6—C14—C15	120.7 (3)
C2—N1—H1A	108.6	N6—C14—H14	119.6
C3—N1—H1A	108.6	C15—C14—H14	119.6
C1—N1—H1A	108.6	C20—C15—C16	118.6 (3)
N1—C3—C4	106.3 (5)	C20—C15—C14	120.6 (3)
N1—C3—H3A	110.5	C16—C15—C14	120.8 (3)
C4—C3—H3A	110.5	C17—C16—C15	120.1 (3)
N1—C3—H3B	110.5	C17—C16—H16	119.9
C4—C3—H3B	110.5	C15—C16—H16	119.9
H3A—C3—H3B	108.7	C16—C17—C18	119.4 (3)
C3—C4—C5	113.7 (5)	C16—C17—H17	120.3
C3—C4—H4A	108.8	C18—C17—H17	120.3
C5—C4—H4A	108.8	C19—C18—C17	122.2 (3)
C3—C4—H4B	108.8	C19—C18—Cl3	118.9 (3)
C5—C4—H4B	108.8	C17—C18—Cl3	119.0 (3)
H4A—C4—H4B	107.7	C18—C19—C20	118.2 (3)
N2—C5—C4	106.7 (4)	C18—C19—H19	120.9
N2—C5—H5A	110.4	C20—C19—H19	120.9
C4—C5—H5A	110.4	C19—C20—C15	121.5 (3)
N2—C5—H5B	110.4	C19—C20—H20	119.3
C4—C5—H5B	110.4	C15—C20—H20	119.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.91	2.19	2.990 (5)	147
N5—H5C···O2	0.86	2.11	2.922 (4)	157
N4—H4C···O1ⁱ	0.86	2.14	2.964 (4)	160
N2—H2D···O7	0.86	2.10	2.873 (5)	149
C19—H19···O2ⁱⁱ	0.93	2.48	3.316 (5)	150
C1—H1D···O6ⁱⁱⁱ	0.96	2.56	3.445 (8)	153
C1—H1C···O6^iv	0.96	2.62	3.555 (10)	166

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₅ClN₆²⁺·2ClO₄⁻
M_r	583.81
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.4533 (18), 10.5018 (18), 12.626 (2)
α, β, γ (°)	104.745 (9), 91.146 (10), 96.21 (1)
V (Å³)	1330.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.25 × 0.23 × 0.18

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.907, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	12435, 4889, 3979
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.219, 1.09
No. of reflections	4889
No. of parameters	371
No. of restraints	62
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.92

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.91	2.19	2.990 (5)	146.7
N5—H5C···O2	0.86	2.11	2.922 (4)	156.8
N4—H4C···O1ⁱ	0.86	2.14	2.964 (4)	159.6
N2—H2D···O7	0.86	2.10	2.873 (5)	148.9
C19—H19···O2ⁱⁱ	0.93	2.48	3.316 (5)	149.7
C1—H1D···O6ⁱⁱⁱ	0.96	2.56	3.445 (8)	153.1
C1—H1C···O6^iv	0.96	2.62	3.555 (10)	165.6

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

Acknowledgements

The authors thank Dalian University of Technology for providing research facilities. This work was supported by the National S & T Major Project of China (No. 2009ZX09301–012) and the S & T Project of Liaoning Province (No. LJQ201107).

References

Abouzid, K. & Shouman, S. (2008). Bioorg. Med. Chem. 16, 7543–7551. Web of Science CrossRef PubMed CAS Google Scholar
An, Z. Y., Yan, Y. Y., Peng, D., Ou, T. M., Tan, J. H., Huang, S. L., An, L. K., Gu, L. Q. & Huang, Z. S. (2010). Eur. J. Med. Chem. 45, 3895–3903. Web of Science CrossRef CAS PubMed Google Scholar
Ferreira, M. L. de, Souza, M. V. N. de, Howie, R. A., Tiekink, E. R. T., Wardell, J. L. & Wardell, S. M. S. V. (2009). Acta Cryst. E65, o3239–o3240. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Loh, W.-S. & Nayak, S. P. (2010). Acta Cryst. E66, o2467. Web of Science CSD CrossRef IUCr Journals Google Scholar
Horiuchi, T., Nagata, M., Kitagawa, M., Akahane, K. & Uoto, K. (2009). Bioorg. Med. Chem. 17, 119–132. Web of Science CrossRef PubMed Google Scholar
Loh, W.-S., Fun, H.-K., Kayarmar, R., Viveka, S. & Nagaraja, G. K. (2011). Acta Cryst. E67, o407–o408. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Souza, M. V. N. de, Howie, R. A., Tiekink, E. R. T., Wardell, J. L. & Wardell, S. M. S. V. (2010). Acta Cryst. E66, o152–o153. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, H. W., Solomon, V. R., Hu, C. K., Ulibarri, G. & Lee, H. Y. (2008). Biomed. Pharmacother. 62, 65–69. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages o1557-o1558

doi:10.1107/S1600536812018272

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-2-[2-(4-Chloro­benzyl­­idene)hydrazin-1-yl]-4-{[3-(di­methyl­aza­nium­yl)prop­yl]amino}­quinazolin-1-ium bis­­(perchlorate)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-2-[2-(4-Chlorobenzylidene)hydrazin-1-yl]-4-{[3-(dimethylazaniumyl)propyl]amino}quinazolin-1-ium bis(perchlorate)