(E)-2-[2-(4-Chloro-benzyl-idene)hydrazin-yl]-4-[3-(morpholin-4-ium-4-yl)propyl-amino]-quinazolin-1-ium bis-(perchlorate).

In the title compound, C(22)H(27)ClN(6)O(2) (2+)·2ClO(4) (-), the mol-ecule adopts an E conformation about the C=N double bond. The quinazoline ring is approximately planar, with an r.m.s. deviation of 0.0432 Å, and forms a dihedral angle of 5.77 (4)° with the chloro-phenyl ring. The crystal packing features N-H⋯O hydrogen bonds.

Related literature

For anti­tumor background to a similar compound, see: Abouzid & Shouman (2008 ▶); Zhang et al. (2008 ▶); An et al. (2010 ▶); Horiuchi et al. (2009 ▶).

Experimental

Crystal data

C22H27ClN6O2+·2ClO4 −

M = 625.85

Monoclinic,

a = 16.1835 (7) Å

b = 11.6719 (4) Å

c = 16.7332 (6) Å

β = 112.127 (3)°

V = 2927.98 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 293 K

0.28 × 0.26 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.903, T max = 0.920

16024 measured reflections

5127 independent reflections

2840 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.215

S = 1.02

5127 reflections

361 parameters

6 restraints

H-atom parameters constrained

Δρmax = 1.13 e Å−3

Δρmin = −0.49 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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/S1600536812021678/vm2162sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021678/vm2162Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021678/vm2162Isup3.cml

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

C22H27ClN6O2+·2ClO4−	F(000) = 1296
Mr = 625.85	Dx = 1.420 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1056 reflections
a = 16.1835 (7) Å	θ = 3.0–19.4°
b = 11.6719 (4) Å	µ = 0.37 mm−1
c = 16.7332 (6) Å	T = 293 K
β = 112.127 (3)°	Block, colorless
V = 2927.98 (19) Å3	0.28 × 0.26 × 0.23 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5127 independent reflections
Radiation source: fine-focus sealed tube	2840 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
phi and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→19
Tmin = 0.903, Tmax = 0.920	k = −13→13
16024 measured reflections	l = −19→19

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.215	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1136P)2] where P = (Fo2 + 2Fc2)/3
5127 reflections	(Δ/σ)max < 0.001
361 parameters	Δρmax = 1.13 e Å−3
6 restraints	Δρmin = −0.49 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
Cl1	0.48875 (8)	0.24389 (10)	0.24289 (8)	0.0469 (4)
Cl2	0.58604 (10)	0.68187 (13)	0.08849 (9)	0.0604 (4)
Cl3	0.64366 (10)	0.15934 (13)	0.86537 (9)	0.0617 (5)
O1	0.4762 (4)	0.6658 (6)	0.0106 (5)	0.149 (3)
O2	0.6449 (3)	0.6308 (5)	0.0545 (3)	0.0987 (17)
O3	0.5925 (4)	0.8078 (4)	0.0946 (3)	0.1027 (17)
O4	0.5874 (3)	0.6329 (5)	0.1671 (3)	0.0980 (17)
O5	0.4191 (4)	0.3417 (5)	0.1669 (4)	0.126 (2)
O6	0.4327 (3)	0.1461 (3)	0.2421 (3)	0.0737 (13)
O7	0.5211 (2)	0.3043 (3)	0.3255 (2)	0.0542 (10)
O8	0.5596 (2)	0.2153 (3)	0.2142 (3)	0.0590 (10)
C1	0.8016 (4)	0.9059 (5)	0.1749 (4)	0.0554 (15)
H1A	0.8556	0.9453	0.2108	0.066*
H1B	0.8110	0.8243	0.1855	0.066*
C2	0.7831 (5)	0.9304 (5)	0.0821 (4)	0.0679 (18)
H2A	0.8333	0.9056	0.0682	0.082*
H2B	0.7309	0.8878	0.0461	0.082*
O9	0.7683 (3)	1.0492 (3)	0.0646 (3)	0.0625 (11)
C3	0.6953 (4)	1.0882 (5)	0.0842 (4)	0.0642 (17)
H4A	0.6415	1.0490	0.0476	0.077*
H4B	0.6869	1.1696	0.0720	0.077*
C4	0.7095 (4)	1.0676 (4)	0.1775 (3)	0.0478 (13)
H5A	0.7603	1.1118	0.2144	0.057*
H5B	0.6574	1.0925	0.1880	0.057*
C5	0.7460 (3)	0.9167 (4)	0.2914 (3)	0.0446 (12)
H6A	0.8030	0.9508	0.3259	0.054*
H6B	0.7522	0.8343	0.2988	0.054*
C6	0.6766 (3)	0.9576 (4)	0.3258 (3)	0.0423 (12)
H7A	0.6719	1.0403	0.3204	0.051*
H7B	0.6970	0.9390	0.3867	0.051*
C7	0.5840 (3)	0.9055 (4)	0.2798 (3)	0.0420 (12)
H8A	0.5603	0.9310	0.2202	0.050*
H8B	0.5892	0.8227	0.2798	0.050*
C8	0.5128 (3)	0.8816 (4)	0.3846 (3)	0.0336 (11)
C9	0.4407 (3)	0.9074 (4)	0.4136 (3)	0.0301 (10)
C10	0.3748 (3)	0.9904 (4)	0.3750 (3)	0.0399 (12)
H11A	0.3781	1.0362	0.3308	0.048*
C11	0.3050 (3)	1.0038 (4)	0.4028 (3)	0.0444 (12)
H12A	0.2609	1.0579	0.3766	0.053*
C12	0.3006 (3)	0.9370 (4)	0.4695 (3)	0.0393 (12)
H13A	0.2534	0.9465	0.4878	0.047*
C13	0.3654 (3)	0.8568 (4)	0.5088 (3)	0.0399 (12)
H14A	0.3626	0.8130	0.5541	0.048*
C14	0.4347 (3)	0.8417 (4)	0.4807 (3)	0.0303 (10)
C15	0.5601 (3)	0.7361 (4)	0.4838 (3)	0.0334 (11)
C16	0.6585 (3)	0.4948 (4)	0.6029 (3)	0.0376 (11)
H17A	0.7037	0.4866	0.5816	0.045*
C17	0.6528 (3)	0.4124 (4)	0.6663 (3)	0.0328 (10)
C18	0.5837 (3)	0.4168 (4)	0.6972 (3)	0.0396 (12)
H19A	0.5393	0.4720	0.6762	0.047*
C19	0.5810 (3)	0.3391 (4)	0.7588 (3)	0.0411 (12)
H20A	0.5358	0.3427	0.7804	0.049*
C20	0.6469 (3)	0.2561 (4)	0.7877 (3)	0.0394 (12)
C21	0.7143 (3)	0.2505 (4)	0.7574 (3)	0.0416 (12)
H22A	0.7582	0.1946	0.7777	0.050*
C22	0.7164 (3)	0.3291 (4)	0.6964 (3)	0.0413 (12)
H23A	0.7620	0.3252	0.6754	0.050*
N1	0.7255 (3)	0.9444 (3)	0.1983 (2)	0.0391 (10)
H1C	0.6759	0.9048	0.1656	0.047*
N2	0.5224 (3)	0.9373 (3)	0.3206 (2)	0.0395 (10)
H2C	0.4898	0.9970	0.3013	0.047*
N3	0.5702 (2)	0.7942 (3)	0.4196 (2)	0.0365 (9)
N4	0.4993 (2)	0.7581 (3)	0.5177 (2)	0.0345 (9)
H4C	0.5000	0.7208	0.5623	0.041*
N5	0.6164 (3)	0.6481 (3)	0.5155 (3)	0.0417 (10)
H5C	0.6596	0.6362	0.4984	0.050*
N6	0.6038 (3)	0.5771 (3)	0.5758 (2)	0.0380 (9)

	U11	U22	U33	U12	U13	U23
Cl1	0.0417 (7)	0.0481 (8)	0.0541 (8)	0.0074 (6)	0.0216 (6)	0.0159 (6)
Cl2	0.0563 (9)	0.0753 (11)	0.0496 (9)	0.0027 (7)	0.0201 (7)	−0.0064 (7)
Cl3	0.0664 (10)	0.0636 (9)	0.0556 (9)	0.0047 (7)	0.0238 (7)	0.0238 (7)
O1	0.099 (5)	0.156 (6)	0.161 (6)	0.003 (4)	0.013 (4)	−0.023 (5)
O2	0.073 (3)	0.165 (5)	0.072 (3)	0.045 (3)	0.043 (3)	0.001 (3)
O3	0.111 (4)	0.071 (3)	0.107 (4)	−0.028 (3)	0.020 (3)	−0.027 (3)
O4	0.089 (3)	0.149 (5)	0.074 (3)	0.048 (3)	0.051 (3)	0.051 (3)
O5	0.126 (5)	0.122 (5)	0.111 (4)	0.023 (4)	0.025 (4)	0.041 (4)
O6	0.055 (2)	0.056 (2)	0.107 (3)	−0.0075 (19)	0.027 (2)	0.030 (2)
O7	0.059 (2)	0.075 (3)	0.035 (2)	0.0039 (19)	0.0237 (18)	0.0051 (18)
O8	0.048 (2)	0.063 (2)	0.078 (3)	0.0027 (18)	0.038 (2)	−0.011 (2)
C1	0.064 (4)	0.054 (3)	0.066 (4)	0.027 (3)	0.045 (3)	0.019 (3)
C2	0.094 (5)	0.058 (4)	0.077 (4)	0.022 (3)	0.062 (4)	0.017 (3)
O9	0.078 (3)	0.059 (2)	0.075 (3)	0.023 (2)	0.057 (2)	0.026 (2)
C3	0.074 (4)	0.067 (4)	0.068 (4)	0.028 (3)	0.045 (3)	0.028 (3)
C4	0.060 (3)	0.034 (3)	0.060 (3)	0.011 (2)	0.034 (3)	0.011 (2)
C5	0.043 (3)	0.054 (3)	0.038 (3)	0.001 (2)	0.017 (2)	0.010 (2)
C6	0.047 (3)	0.047 (3)	0.041 (3)	−0.006 (2)	0.026 (2)	−0.003 (2)
C7	0.047 (3)	0.049 (3)	0.037 (3)	−0.004 (2)	0.024 (2)	0.003 (2)
C8	0.037 (3)	0.035 (3)	0.031 (3)	−0.008 (2)	0.015 (2)	−0.002 (2)
C9	0.031 (2)	0.032 (2)	0.028 (2)	−0.0028 (19)	0.012 (2)	−0.0032 (19)
C10	0.045 (3)	0.039 (3)	0.038 (3)	0.001 (2)	0.017 (2)	0.006 (2)
C11	0.039 (3)	0.049 (3)	0.046 (3)	0.008 (2)	0.016 (2)	0.002 (2)
C12	0.036 (3)	0.049 (3)	0.037 (3)	0.001 (2)	0.018 (2)	0.000 (2)
C13	0.041 (3)	0.044 (3)	0.036 (3)	−0.002 (2)	0.017 (2)	0.001 (2)
C14	0.034 (2)	0.032 (2)	0.026 (2)	−0.004 (2)	0.013 (2)	−0.0028 (19)
C15	0.035 (3)	0.036 (3)	0.030 (3)	−0.002 (2)	0.014 (2)	0.000 (2)
C16	0.040 (3)	0.038 (3)	0.038 (3)	0.000 (2)	0.018 (2)	−0.001 (2)
C17	0.037 (3)	0.031 (2)	0.032 (2)	0.003 (2)	0.016 (2)	−0.0003 (19)
C18	0.039 (3)	0.036 (3)	0.044 (3)	0.008 (2)	0.016 (2)	0.009 (2)
C19	0.040 (3)	0.045 (3)	0.042 (3)	−0.001 (2)	0.020 (2)	0.000 (2)
C20	0.046 (3)	0.036 (3)	0.034 (3)	−0.004 (2)	0.012 (2)	0.004 (2)
C21	0.043 (3)	0.041 (3)	0.038 (3)	0.009 (2)	0.012 (2)	0.005 (2)
C22	0.040 (3)	0.042 (3)	0.045 (3)	0.006 (2)	0.020 (2)	0.000 (2)
N1	0.045 (2)	0.036 (2)	0.043 (2)	0.0045 (18)	0.024 (2)	0.0054 (18)
N2	0.045 (2)	0.040 (2)	0.042 (2)	0.0005 (18)	0.025 (2)	0.0079 (18)
N3	0.038 (2)	0.043 (2)	0.033 (2)	0.0021 (19)	0.0182 (18)	0.0058 (18)
N4	0.042 (2)	0.038 (2)	0.030 (2)	0.0042 (18)	0.0201 (18)	0.0085 (17)
N5	0.045 (2)	0.043 (2)	0.045 (2)	0.0109 (19)	0.026 (2)	0.0099 (19)
N6	0.048 (2)	0.034 (2)	0.037 (2)	0.0015 (19)	0.021 (2)	0.0052 (17)

Cl1—O8	1.440 (3)	C8—N3	1.355 (6)
Cl1—O6	1.455 (4)	C8—C9	1.455 (6)
Cl1—O7	1.462 (4)	C9—C14	1.393 (6)
Cl1—O5	1.764 (5)	C9—C10	1.404 (6)
Cl2—O2	1.412 (4)	C10—C11	1.384 (6)
Cl2—O4	1.427 (4)	C10—H11A	0.9300
Cl2—O3	1.474 (5)	C11—C12	1.385 (7)
Cl2—O1	1.774 (7)	C11—H12A	0.9300
Cl3—C20	1.737 (5)	C12—C13	1.374 (6)
C1—C2	1.493 (7)	C12—H13A	0.9300
C1—N1	1.496 (6)	C13—C14	1.382 (6)
C1—H1A	0.9700	C13—H14A	0.9300
C1—H1B	0.9700	C14—N4	1.393 (6)
C2—O9	1.418 (6)	C15—N3	1.331 (5)
C2—H2A	0.9700	C15—N4	1.332 (5)
C2—H2B	0.9700	C15—N5	1.343 (6)
O9—C3	1.415 (6)	C16—N6	1.269 (6)
C3—C4	1.509 (7)	C16—C17	1.461 (6)
C3—H4A	0.9700	C16—H17A	0.9300
C3—H4B	0.9700	C17—C22	1.366 (6)
C4—N1	1.478 (6)	C17—C18	1.398 (6)
C4—H5A	0.9700	C18—C19	1.387 (6)
C4—H5B	0.9700	C18—H19A	0.9300
C5—N1	1.500 (6)	C19—C20	1.387 (7)
C5—C6	1.518 (6)	C19—H20A	0.9300
C5—H6A	0.9700	C20—C21	1.366 (7)
C5—H6B	0.9700	C21—C22	1.383 (6)
C6—C7	1.530 (7)	C21—H22A	0.9300
C6—H7A	0.9700	C22—H23A	0.9300
C6—H7B	0.9700	N1—H1C	0.9100
C7—N2	1.453 (6)	N2—H2C	0.8600
C7—H8A	0.9700	N4—H4C	0.8600
C7—H8B	0.9700	N5—N6	1.379 (5)
C8—N2	1.311 (5)	N5—H5C	0.8600
O8—Cl1—O6	112.8 (2)	C14—C9—C8	117.6 (4)
O8—Cl1—O7	112.4 (2)	C10—C9—C8	123.7 (4)
O6—Cl1—O7	112.7 (2)	C11—C10—C9	119.8 (4)
O8—Cl1—O5	106.4 (3)	C11—C10—H11A	120.1
O6—Cl1—O5	105.9 (3)	C9—C10—H11A	120.1
O7—Cl1—O5	105.9 (3)	C10—C11—C12	120.3 (5)
O2—Cl2—O4	115.1 (3)	C10—C11—H12A	119.9
O2—Cl2—O3	114.1 (3)	C12—C11—H12A	119.9
O4—Cl2—O3	111.1 (3)	C13—C12—C11	120.5 (5)
O2—Cl2—O1	107.5 (3)	C13—C12—H13A	119.7
O4—Cl2—O1	107.3 (4)	C11—C12—H13A	119.7
O3—Cl2—O1	100.4 (3)	C12—C13—C14	119.7 (4)
C2—C1—N1	110.6 (4)	C12—C13—H14A	120.2
C2—C1—H1A	109.5	C14—C13—H14A	120.2
N1—C1—H1A	109.5	C13—C14—C9	121.1 (4)
C2—C1—H1B	109.5	C13—C14—N4	120.5 (4)
N1—C1—H1B	109.5	C9—C14—N4	118.4 (4)
H1A—C1—H1B	108.1	N3—C15—N4	125.5 (4)
O9—C2—C1	110.7 (5)	N3—C15—N5	115.8 (4)
O9—C2—H2A	109.5	N4—C15—N5	118.7 (4)
C1—C2—H2A	109.5	N6—C16—C17	122.1 (4)
O9—C2—H2B	109.5	N6—C16—H17A	119.0
C1—C2—H2B	109.5	C17—C16—H17A	119.0
H2A—C2—H2B	108.1	C22—C17—C18	119.1 (4)
C3—O9—C2	111.0 (4)	C22—C17—C16	119.4 (4)
O9—C3—C4	111.9 (5)	C18—C17—C16	121.5 (4)
O9—C3—H4A	109.2	C19—C18—C17	120.3 (4)
C4—C3—H4A	109.2	C19—C18—H19A	119.8
O9—C3—H4B	109.2	C17—C18—H19A	119.8
C4—C3—H4B	109.2	C20—C19—C18	118.7 (4)
H4A—C3—H4B	107.9	C20—C19—H20A	120.6
N1—C4—C3	110.2 (4)	C18—C19—H20A	120.6
N1—C4—H5A	109.6	C21—C20—C19	121.4 (4)
C3—C4—H5A	109.6	C21—C20—Cl3	120.0 (4)
N1—C4—H5B	109.6	C19—C20—Cl3	118.6 (4)
C3—C4—H5B	109.6	C20—C21—C22	119.2 (4)
H5A—C4—H5B	108.1	C20—C21—H22A	120.4
N1—C5—C6	114.8 (4)	C22—C21—H22A	120.4
N1—C5—H6A	108.6	C17—C22—C21	121.3 (5)
C6—C5—H6A	108.6	C17—C22—H23A	119.3
N1—C5—H6B	108.6	C21—C22—H23A	119.3
C6—C5—H6B	108.6	C4—N1—C1	108.6 (4)
H6A—C5—H6B	107.5	C4—N1—C5	113.9 (4)
C5—C6—C7	114.1 (4)	C1—N1—C5	109.0 (4)
C5—C6—H7A	108.7	C4—N1—H1C	108.4
C7—C6—H7A	108.7	C1—N1—H1C	108.4
C5—C6—H7B	108.7	C5—N1—H1C	108.4
C7—C6—H7B	108.7	C8—N2—C7	124.8 (4)
H7A—C6—H7B	107.6	C8—N2—H2C	117.6
N2—C7—C6	112.2 (4)	C7—N2—H2C	117.6
N2—C7—H8A	109.2	C15—N3—C8	117.4 (4)
C6—C7—H8A	109.2	C15—N4—C14	119.8 (4)
N2—C7—H8B	109.2	C15—N4—H4C	120.1
C6—C7—H8B	109.2	C14—N4—H4C	120.1
H8A—C7—H8B	107.9	C15—N5—N6	118.9 (4)
N2—C8—N3	117.0 (4)	C15—N5—H5C	120.6
N2—C8—C9	121.8 (4)	N6—N5—H5C	120.6
N3—C8—C9	121.1 (4)	C16—N6—N5	116.1 (4)
C14—C9—C10	118.7 (4)
N1—C1—C2—O9	58.6 (7)	C18—C19—C20—Cl3	179.7 (4)
C1—C2—O9—C3	−59.2 (7)	C19—C20—C21—C22	−0.4 (7)
C2—O9—C3—C4	58.6 (7)	Cl3—C20—C21—C22	−179.2 (4)
O9—C3—C4—N1	−57.0 (6)	C18—C17—C22—C21	−0.9 (7)
N1—C5—C6—C7	61.1 (6)	C16—C17—C22—C21	179.0 (4)
C5—C6—C7—N2	173.8 (4)	C20—C21—C22—C17	0.4 (7)
N2—C8—C9—C14	178.4 (4)	C3—C4—N1—C1	54.8 (6)
N3—C8—C9—C14	2.2 (6)	C3—C4—N1—C5	176.4 (4)
N2—C8—C9—C10	1.8 (7)	C2—C1—N1—C4	−56.3 (6)
N3—C8—C9—C10	−174.4 (4)	C2—C1—N1—C5	179.1 (5)
C14—C9—C10—C11	−1.2 (7)	C6—C5—N1—C4	55.1 (6)
C8—C9—C10—C11	175.4 (4)	C6—C5—N1—C1	176.5 (4)
C9—C10—C11—C12	1.0 (7)	N3—C8—N2—C7	6.0 (7)
C10—C11—C12—C13	0.1 (7)	C9—C8—N2—C7	−170.4 (4)
C11—C12—C13—C14	−1.0 (7)	C6—C7—N2—C8	−87.4 (6)
C12—C13—C14—C9	0.8 (7)	N4—C15—N3—C8	−1.4 (7)
C12—C13—C14—N4	−177.7 (4)	N5—C15—N3—C8	178.2 (4)
C10—C9—C14—C13	0.3 (6)	N2—C8—N3—C15	−179.0 (4)
C8—C9—C14—C13	−176.5 (4)	C9—C8—N3—C15	−2.6 (6)
C10—C9—C14—N4	178.8 (4)	N3—C15—N4—C14	5.7 (7)
C8—C9—C14—N4	2.0 (6)	N5—C15—N4—C14	−173.9 (4)
N6—C16—C17—C22	−176.6 (4)	C13—C14—N4—C15	172.7 (4)
N6—C16—C17—C18	3.3 (7)	C9—C14—N4—C15	−5.8 (6)
C22—C17—C18—C19	1.4 (7)	N3—C15—N5—N6	−173.4 (4)
C16—C17—C18—C19	−178.5 (4)	N4—C15—N5—N6	6.3 (6)
C17—C18—C19—C20	−1.3 (7)	C17—C16—N6—N5	−179.6 (4)
C18—C19—C20—C21	0.8 (7)	C15—N5—N6—C16	179.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O3	0.91	1.82	2.717 (6)	168
N2—H2C···O6i	0.86	2.04	2.888 (5)	167
N4—H4C···O7ii	0.86	2.05	2.859 (5)	156
N5—H5C···O9iii	0.86	2.11	2.915 (5)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O3	0.91	1.82	2.717 (6)	168
N2—H2C⋯O6i	0.86	2.04	2.888 (5)	167
N4—H4C⋯O7ii	0.86	2.05	2.859 (5)	156
N5—H5C⋯O9iii	0.86	2.11	2.915 (5)	157

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