(E)-2-[2-(4-Chloro-benzyl-idene)hydrazin-1-yl]-4-{[3-(dimethyl-aza-nium-yl)prop-yl]amino}-quinazolin-1-ium bis-(perchlorate).

In the title compound, C(20)H(25)ClN(6) (2+)·2ClO(4) (-), the organic cation is roughly planar, as shown by the dihedral angle of 3.78 (3)° between the quinazoline and chloro-phenyl 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 (dimethyl-aza-nium-yl)propyl-amino 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

C20H25ClN6 2+·2ClO4 −

M = 583.81

Triclinic,

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[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.219

S = 1.09

4889 reflections

371 parameters

62 restraints

H-atom parameters constrained

Δρmax = 0.69 e Å−3

Δρmin = −0.92 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018272/im2363sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812018272/im2363Isup3.cml

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

C20H25ClN62+·2ClO4−	Z = 2
Mr = 583.81	F(000) = 604
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.1339P)2 + 1.0689P] where P = (Fo2 + 2Fc2)/3
4889 reflections	(Δ/σ)max < 0.001
371 parameters	Δρmax = 0.69 e Å−3
62 restraints	Δρmin = −0.92 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	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*

	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)

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

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···O6iv	0.96	2.62	3.555 (10)	166

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⋯O6iv	0.96	2.62	3.555 (10)	166

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .