2,2'-Dimethyl-7,7'-(methyl-enediimino)di-1,8-naphthyridin-1-ium bis-(perchlorate).

In the title salt, C(19)H(20)N(6) (2+)·2ClO(4) (-), the two planar 1,8-naphthyridine systems are linked by a methyl-enediamine group with a dihedral angle of 60.6 (1)° between the two systems. The crystal structure involves extensive N-H⋯O and C-H⋯O hydrogen bonding.

Related literature

For related literature, see: Baker & Norman (2004 ▶); Gavrilova & Bosnich (2004 ▶); Nakatani et al. (2000 ▶, 2001 ▶); Stadie et al. (2007 ▶); Ferrarini et al. (1997 ▶).

Experimental

Crystal data

C19H20N6 2+·2ClO4 −

M = 531.31

Orthorhombic,

a = 8.191 (1) Å

b = 19.325 (2) Å

c = 27.885 (2) Å

V = 4413.9 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.36 mm−1

T = 113 (2) K

0.34 × 0.16 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.908, T max = 0.952

31220 measured reflections

3882 independent reflections

3598 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.134

S = 1.16

3882 reflections

308 parameters

16 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.41 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: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: XP in SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024616/hg2415sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024616/hg2415Isup2.hkl

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

C19H20N62+·2ClO4–	F000 = 2192
Mr = 531.31	Dx = 1.599 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7263 reflections
a = 8.1910 (5) Å	θ = 2.1–28.0º
b = 19.3250 (12) Å	µ = 0.36 mm−1
c = 27.8850 (19) Å	T = 113 (2) K
V = 4413.9 (5) Å3	Prism, colorless
Z = 8	0.34 × 0.16 × 0.14 mm

Bruker SMART CCD area-detector diffractometer	3882 independent reflections
Radiation source: fine-focus sealed tube	3598 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.061
Detector resolution: 7.31 pixels mm-1	θmax = 25.0º
T = 113(2) K	θmin = 2.1º
φ and ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	k = −22→22
Tmin = 0.909, Tmax = 0.952	l = −33→32
31220 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0498P)2 + 5.3196P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.003
3882 reflections	Δρmax = 0.35 e Å−3
308 parameters	Δρmin = −0.41 e Å−3
16 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.24246 (10)	0.22574 (4)	0.56855 (3)	0.0360 (2)
Cl2	1.00163 (9)	0.01682 (3)	0.69459 (3)	0.0323 (2)
O1	0.1693 (6)	0.1730 (2)	0.59780 (16)	0.0534 (14)	0.747 (5)
O2	0.3894 (5)	0.2014 (2)	0.5483 (2)	0.0758 (17)	0.747 (5)
O3	0.1302 (6)	0.2438 (2)	0.53084 (12)	0.0738 (15)	0.747 (5)
O4	0.2651 (6)	0.28664 (19)	0.59698 (15)	0.0700 (14)	0.747 (5)
O5	0.8509 (4)	0.02894 (17)	0.67091 (14)	0.0664 (12)	0.870 (6)
O6	0.9850 (5)	−0.03196 (14)	0.73264 (10)	0.0657 (13)	0.870 (6)
O7	1.1129 (3)	−0.01123 (15)	0.65972 (10)	0.0490 (10)	0.870 (6)
O8	1.0661 (6)	0.0802 (2)	0.7134 (2)	0.0444 (13)	0.870 (6)
O1'	0.1358 (14)	0.1676 (5)	0.5766 (4)	0.039 (3)	0.253 (5)
O2'	0.3710 (11)	0.2233 (6)	0.6037 (3)	0.062 (4)	0.253 (5)
O3'	0.3135 (14)	0.2178 (6)	0.5220 (3)	0.062 (4)	0.253 (5)
O4'	0.1558 (13)	0.2875 (4)	0.5708 (4)	0.052 (3)	0.253 (5)
O5'	0.8301 (12)	0.0031 (10)	0.7058 (7)	0.053 (6)	0.130 (6)
O6'	1.0870 (19)	−0.0453 (6)	0.7069 (7)	0.048 (6)	0.130 (6)
O7'	1.012 (3)	0.0307 (10)	0.6446 (4)	0.062 (7)	0.130 (6)
O8'	1.056 (3)	0.0738 (10)	0.7228 (8)	0.039 (10)	0.130 (6)
N1	0.1466 (3)	0.16498 (13)	0.27420 (9)	0.0328 (6)
N2	0.1460 (3)	0.16453 (12)	0.35633 (8)	0.0293 (6)
N3	0.1396 (3)	0.16601 (15)	0.43819 (10)	0.0353 (6)
N6	0.3295 (3)	0.04505 (14)	0.58097 (9)	0.0336 (6)
N5	0.2041 (3)	0.04253 (13)	0.50731 (9)	0.0327 (6)
N4	0.0922 (4)	0.04231 (16)	0.43264 (11)	0.0417 (7)
C2	0.1739 (4)	0.19127 (16)	0.23034 (10)	0.0377 (8)
C3	0.2463 (5)	0.25570 (18)	0.22665 (11)	0.0435 (9)
H3	0.2634	0.2759	0.1960	0.052*
C4	0.2935 (4)	0.29061 (16)	0.26746 (11)	0.0390 (8)
H4	0.3453	0.3344	0.2647	0.047*
C5	0.2662 (4)	0.26239 (14)	0.31277 (10)	0.0285 (7)
C6	0.1858 (4)	0.19774 (14)	0.31595 (10)	0.0268 (6)
C7	0.1866 (4)	0.19636 (15)	0.39716 (10)	0.0288 (7)
C8	0.2786 (4)	0.25928 (15)	0.39855 (10)	0.0314 (7)
H8	0.3132	0.2779	0.4284	0.038*
C9	0.3159 (4)	0.29193 (15)	0.35722 (10)	0.0324 (7)
H9	0.3748	0.3343	0.3578	0.039*
C1	0.1243 (6)	0.14783 (18)	0.18868 (12)	0.0518 (10)
H1A	0.2123	0.1154	0.1808	0.078*
H1B	0.1026	0.1776	0.1610	0.078*
H1C	0.0253	0.1219	0.1968	0.078*
C16	0.4320 (4)	0.02351 (16)	0.61578 (11)	0.0360 (8)
C17	0.5112 (4)	−0.03943 (17)	0.60916 (12)	0.0402 (8)
H17	0.5862	−0.0556	0.6326	0.048*
C18	0.4812 (4)	−0.07835 (17)	0.56878 (12)	0.0398 (8)
H18	0.5322	−0.1222	0.5653	0.048*
C14	0.3773 (4)	−0.05443 (15)	0.53293 (12)	0.0357 (7)
C15	0.3015 (4)	0.01043 (16)	0.53928 (11)	0.0316 (7)
C11	0.1802 (4)	0.00934 (17)	0.46592 (11)	0.0368 (8)
C12	0.2463 (4)	−0.05808 (16)	0.45608 (12)	0.0424 (8)
H12	0.2221	−0.0808	0.4267	0.051*
C13	0.3428 (4)	−0.08878 (16)	0.48880 (12)	0.0411 (8)
H13	0.3878	−0.1332	0.4825	0.049*
C19	0.4554 (5)	0.06921 (19)	0.65809 (11)	0.0446 (8)
H19A	0.4863	0.1156	0.6473	0.067*
H19B	0.5418	0.0503	0.6785	0.067*
H19C	0.3533	0.0718	0.6763	0.067*
C10	0.0224 (4)	0.10976 (18)	0.43970 (12)	0.0431 (8)
H10A	−0.0336	0.1106	0.4712	0.052*
H10B	−0.0612	0.1178	0.4147	0.052*
H3A	0.163 (4)	0.1865 (17)	0.4619 (12)	0.035 (10)*
H1	0.101 (5)	0.124 (2)	0.2764 (13)	0.055 (11)*
H4A	0.081 (5)	0.0269 (19)	0.4097 (13)	0.040 (12)*
H6	0.281 (4)	0.0828 (18)	0.5853 (12)	0.035 (9)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0433 (5)	0.0317 (4)	0.0331 (4)	−0.0003 (3)	0.0046 (4)	−0.0008 (3)
Cl2	0.0360 (5)	0.0256 (4)	0.0353 (4)	−0.0007 (3)	0.0018 (3)	−0.0012 (3)
O1	0.064 (3)	0.046 (2)	0.050 (3)	0.016 (2)	0.026 (2)	0.022 (2)
O2	0.055 (3)	0.049 (2)	0.124 (4)	−0.002 (2)	0.053 (3)	−0.011 (3)
O3	0.118 (4)	0.059 (2)	0.045 (2)	0.031 (2)	−0.025 (2)	0.0033 (18)
O4	0.089 (3)	0.052 (2)	0.070 (3)	−0.001 (2)	0.002 (3)	−0.027 (2)
O5	0.0421 (19)	0.063 (2)	0.095 (3)	0.0139 (15)	−0.0291 (19)	−0.019 (2)
O6	0.126 (4)	0.0396 (16)	0.0313 (15)	−0.0408 (19)	−0.0042 (19)	0.0050 (12)
O7	0.0410 (17)	0.0542 (18)	0.0519 (18)	−0.0075 (14)	0.0127 (14)	−0.0213 (14)
O8	0.055 (3)	0.0232 (18)	0.055 (2)	−0.0038 (16)	−0.002 (2)	−0.0076 (17)
O1'	0.036 (6)	0.030 (5)	0.051 (7)	−0.003 (4)	0.014 (5)	0.002 (5)
O2'	0.049 (6)	0.086 (7)	0.052 (6)	−0.022 (5)	−0.013 (5)	0.031 (5)
O3'	0.056 (7)	0.087 (7)	0.041 (6)	−0.016 (6)	0.023 (5)	−0.020 (5)
O4'	0.063 (6)	0.027 (4)	0.065 (6)	0.017 (4)	0.012 (5)	0.007 (4)
O5'	0.030 (8)	0.067 (9)	0.061 (10)	0.008 (7)	0.004 (7)	0.003 (8)
O6'	0.046 (9)	0.033 (8)	0.064 (10)	0.009 (7)	0.000 (8)	0.003 (7)
O7'	0.085 (11)	0.060 (10)	0.041 (9)	−0.012 (8)	0.014 (8)	−0.003 (7)
O8'	0.053 (14)	0.032 (13)	0.032 (12)	0.002 (8)	−0.006 (8)	−0.010 (8)
N1	0.0448 (17)	0.0233 (13)	0.0302 (14)	−0.0046 (12)	−0.0070 (12)	0.0000 (10)
N2	0.0321 (14)	0.0275 (12)	0.0283 (13)	−0.0027 (11)	−0.0009 (11)	0.0035 (10)
N3	0.0381 (16)	0.0419 (15)	0.0260 (14)	0.0023 (13)	−0.0004 (12)	0.0032 (12)
N6	0.0353 (15)	0.0344 (15)	0.0310 (14)	0.0059 (13)	0.0054 (12)	0.0103 (12)
N5	0.0314 (14)	0.0360 (14)	0.0306 (13)	−0.0023 (11)	0.0053 (11)	0.0101 (11)
N4	0.0479 (19)	0.0467 (18)	0.0306 (16)	−0.0128 (14)	−0.0024 (15)	0.0084 (14)
C2	0.053 (2)	0.0331 (16)	0.0266 (16)	0.0011 (15)	−0.0066 (15)	−0.0008 (13)
C3	0.064 (2)	0.0381 (18)	0.0287 (16)	−0.0036 (17)	−0.0008 (16)	0.0063 (14)
C4	0.050 (2)	0.0317 (16)	0.0349 (17)	−0.0098 (15)	0.0017 (15)	0.0043 (13)
C5	0.0341 (17)	0.0212 (14)	0.0302 (15)	−0.0031 (12)	−0.0020 (13)	−0.0004 (12)
C6	0.0325 (16)	0.0223 (13)	0.0257 (14)	−0.0012 (12)	−0.0021 (13)	−0.0003 (11)
C7	0.0299 (16)	0.0301 (15)	0.0264 (15)	0.0067 (13)	0.0012 (13)	0.0022 (12)
C8	0.0359 (18)	0.0293 (15)	0.0290 (15)	0.0050 (13)	−0.0035 (13)	−0.0066 (12)
C9	0.0374 (18)	0.0262 (15)	0.0335 (16)	−0.0018 (13)	−0.0029 (14)	−0.0030 (12)
C1	0.083 (3)	0.0408 (19)	0.0316 (18)	−0.0031 (19)	−0.0128 (19)	−0.0052 (15)
C16	0.0290 (17)	0.0429 (18)	0.0362 (17)	−0.0019 (14)	0.0067 (14)	0.0172 (14)
C17	0.0313 (18)	0.0449 (19)	0.0444 (19)	0.0015 (15)	0.0056 (15)	0.0222 (16)
C18	0.0337 (18)	0.0324 (17)	0.053 (2)	0.0026 (14)	0.0174 (16)	0.0202 (15)
C14	0.0355 (18)	0.0285 (15)	0.0430 (18)	−0.0041 (14)	0.0150 (15)	0.0115 (14)
C15	0.0287 (17)	0.0350 (16)	0.0309 (16)	−0.0028 (13)	0.0097 (13)	0.0104 (13)
C11	0.0381 (19)	0.0409 (18)	0.0314 (16)	−0.0138 (15)	0.0053 (15)	0.0099 (14)
C12	0.052 (2)	0.0331 (17)	0.0417 (19)	−0.0172 (16)	0.0116 (17)	0.0006 (15)
C13	0.048 (2)	0.0273 (16)	0.048 (2)	−0.0080 (15)	0.0165 (17)	0.0061 (14)
C19	0.042 (2)	0.058 (2)	0.0341 (17)	−0.0008 (17)	0.0011 (16)	0.0121 (16)
C10	0.0343 (19)	0.061 (2)	0.0343 (18)	−0.0038 (17)	0.0030 (15)	0.0176 (16)

Cl1—O4'	1.390 (7)	C2—C3	1.383 (5)
Cl1—O2	1.410 (4)	C2—C1	1.490 (4)
Cl1—O3'	1.430 (7)	C3—C4	1.378 (4)
Cl1—O4	1.431 (3)	C3—H3	0.9500
Cl1—O1	1.436 (4)	C4—C5	1.394 (4)
Cl1—O2'	1.439 (7)	C4—H4	0.9500
Cl1—O3	1.440 (3)	C5—C6	1.415 (4)
Cl1—O1'	1.441 (8)	C5—C9	1.424 (4)
Cl2—O5	1.420 (3)	C7—C8	1.431 (4)
Cl2—O7'	1.423 (9)	C8—C9	1.349 (4)
Cl2—O8'	1.424 (10)	C8—H8	0.9500
Cl2—O6	1.426 (3)	C9—H9	0.9500
Cl2—O6'	1.432 (9)	C1—H1A	0.9800
Cl2—O8	1.433 (3)	C1—H1B	0.9800
Cl2—O7	1.439 (3)	C1—H1C	0.9800
Cl2—O5'	1.464 (9)	C16—C17	1.390 (5)
N1—C2	1.343 (4)	C16—C19	1.486 (5)
N1—C6	1.364 (4)	C17—C18	1.376 (5)
N1—H1	0.88 (4)	C17—H17	0.9500
N2—C7	1.336 (4)	C18—C14	1.392 (5)
N2—C6	1.336 (4)	C18—H18	0.9500
N3—C7	1.342 (4)	C14—C15	1.410 (4)
N3—C10	1.451 (4)	C14—C13	1.427 (5)
N3—H3A	0.80 (3)	C11—C12	1.437 (5)
N6—C16	1.350 (4)	C12—C13	1.345 (5)
N6—C15	1.360 (4)	C12—H12	0.9500
N6—H6	0.84 (3)	C13—H13	0.9500
N5—C11	1.335 (4)	C19—H19A	0.9800
N5—C15	1.348 (4)	C19—H19B	0.9800
N4—C11	1.337 (4)	C19—H19C	0.9800
N4—C10	1.437 (5)	C10—H10A	0.9900
N4—H4A	0.71 (4)	C10—H10B	0.9900
O4'—Cl1—O2	137.8 (4)	N1—C2—C3	118.7 (3)
O4'—Cl1—O3'	109.9 (6)	N1—C2—C1	116.8 (3)
O4'—Cl1—O4	48.3 (4)	C3—C2—C1	124.5 (3)
O2—Cl1—O4	112.7 (3)	C4—C3—C2	120.0 (3)
O3'—Cl1—O4	122.6 (5)	C4—C3—H3	120.0
O4'—Cl1—O1	111.8 (5)	C2—C3—H3	120.0
O2—Cl1—O1	110.3 (3)	C3—C4—C5	120.8 (3)
O3'—Cl1—O1	127.5 (5)	C3—C4—H4	119.6
O4—Cl1—O1	108.9 (3)	C5—C4—H4	119.6
O4'—Cl1—O2'	111.7 (6)	C4—C5—C6	118.5 (3)
O2—Cl1—O2'	68.8 (5)	C4—C5—C9	125.9 (3)
O3'—Cl1—O2'	108.5 (6)	C6—C5—C9	115.6 (3)
O4—Cl1—O2'	63.6 (5)	N2—C6—N1	116.0 (2)
O1—Cl1—O2'	84.0 (4)	N2—C6—C5	126.2 (3)
O4'—Cl1—O3	59.9 (5)	N1—C6—C5	117.8 (3)
O2—Cl1—O3	109.5 (3)	N2—C7—N3	117.0 (3)
O3'—Cl1—O3	67.9 (5)	N2—C7—C8	123.0 (3)
O4—Cl1—O3	106.7 (2)	N3—C7—C8	120.0 (3)
O1—Cl1—O3	108.7 (3)	C9—C8—C7	119.6 (3)
O2'—Cl1—O3	166.5 (4)	C9—C8—H8	120.2
O4'—Cl1—O1'	110.7 (6)	C7—C8—H8	120.2
O2—Cl1—O1'	108.6 (6)	C8—C9—C5	119.4 (3)
O3'—Cl1—O1'	107.7 (6)	C8—C9—H9	120.3
O4—Cl1—O1'	129.3 (5)	C5—C9—H9	120.3
O2'—Cl1—O1'	108.2 (6)	C2—C1—H1A	109.5
O3—Cl1—O1'	85.2 (5)	C2—C1—H1B	109.5
O5—Cl2—O7'	64.3 (8)	H1A—C1—H1B	109.5
O5—Cl2—O8'	113.6 (11)	C2—C1—H1C	109.5
O7'—Cl2—O8'	112.1 (10)	H1A—C1—H1C	109.5
O5—Cl2—O6	111.8 (2)	H1B—C1—H1C	109.5
O7'—Cl2—O6	149.3 (8)	N6—C16—C17	117.7 (3)
O8'—Cl2—O6	97.5 (11)	N6—C16—C19	117.9 (3)
O5—Cl2—O6'	132.4 (7)	C17—C16—C19	124.4 (3)
O7'—Cl2—O6'	111.3 (8)	C18—C17—C16	120.2 (3)
O8'—Cl2—O6'	111.4 (10)	C18—C17—H17	119.9
O6—Cl2—O6'	46.6 (7)	C16—C17—H17	119.9
O5—Cl2—O8	110.5 (2)	C17—C18—C14	121.0 (3)
O7'—Cl2—O8	100.1 (8)	C17—C18—H18	119.5
O6—Cl2—O8	109.1 (3)	C14—C18—H18	119.5
O6'—Cl2—O8	116.7 (8)	C18—C14—C15	118.3 (3)
O5—Cl2—O7	107.38 (19)	C18—C14—C13	125.9 (3)
O7'—Cl2—O7	50.9 (8)	C15—C14—C13	115.8 (3)
O8'—Cl2—O7	117.9 (11)	N5—C15—N6	116.0 (3)
O6—Cl2—O7	108.3 (2)	N5—C15—C14	125.9 (3)
O6'—Cl2—O7	62.4 (8)	N6—C15—C14	118.1 (3)
O8—Cl2—O7	109.6 (3)	N5—C11—N4	116.8 (3)
O5—Cl2—O5'	45.2 (7)	N5—C11—C12	123.1 (3)
O7'—Cl2—O5'	107.7 (8)	N4—C11—C12	120.2 (3)
O8'—Cl2—O5'	108.7 (10)	C13—C12—C11	119.5 (3)
O6—Cl2—O5'	68.2 (8)	C13—C12—H12	120.3
O6'—Cl2—O5'	105.3 (8)	C11—C12—H12	120.3
O8—Cl2—O5'	115.5 (8)	C12—C13—C14	119.8 (3)
O7—Cl2—O5'	133.2 (8)	C12—C13—H13	120.1
C2—N1—C6	124.2 (3)	C14—C13—H13	120.1
C2—N1—H1	118 (2)	C16—C19—H19A	109.5
C6—N1—H1	117 (2)	C16—C19—H19B	109.5
C7—N2—C6	115.9 (2)	H19A—C19—H19B	109.5
C7—N3—C10	122.8 (3)	C16—C19—H19C	109.5
C7—N3—H3A	115 (2)	H19A—C19—H19C	109.5
C10—N3—H3A	121 (2)	H19B—C19—H19C	109.5
C16—N6—C15	124.6 (3)	N4—C10—N3	114.4 (3)
C16—N6—H6	117 (2)	N4—C10—H10A	108.7
C15—N6—H6	118 (2)	N3—C10—H10A	108.7
C11—N5—C15	116.0 (3)	N4—C10—H10B	108.7
C11—N4—C10	123.5 (3)	N3—C10—H10B	108.7
C11—N4—H4A	120 (3)	H10A—C10—H10B	107.6
C10—N4—H4A	117 (3)
C6—N1—C2—C3	−0.1 (5)	C15—N6—C16—C19	176.9 (3)
C6—N1—C2—C1	179.5 (3)	N6—C16—C17—C18	−1.5 (4)
N1—C2—C3—C4	2.1 (5)	C19—C16—C17—C18	179.8 (3)
C1—C2—C3—C4	−177.4 (4)	C16—C17—C18—C14	2.8 (5)
C2—C3—C4—C5	−1.4 (6)	C17—C18—C14—C15	−0.8 (4)
C3—C4—C5—C6	−1.3 (5)	C17—C18—C14—C13	177.1 (3)
C3—C4—C5—C9	177.0 (3)	C11—N5—C15—N6	178.3 (3)
C7—N2—C6—N1	179.2 (3)	C11—N5—C15—C14	−0.7 (4)
C7—N2—C6—C5	0.2 (4)	C16—N6—C15—N5	−175.3 (3)
C2—N1—C6—N2	178.4 (3)	C16—N6—C15—C14	3.8 (4)
C2—N1—C6—C5	−2.5 (5)	C18—C14—C15—N5	176.7 (3)
C4—C5—C6—N2	−177.9 (3)	C13—C14—C15—N5	−1.5 (4)
C9—C5—C6—N2	3.7 (5)	C18—C14—C15—N6	−2.3 (4)
C4—C5—C6—N1	3.1 (4)	C13—C14—C15—N6	179.5 (3)
C9—C5—C6—N1	−175.3 (3)	C15—N5—C11—N4	−176.0 (3)
C6—N2—C7—N3	176.2 (3)	C15—N5—C11—C12	3.0 (4)
C6—N2—C7—C8	−4.9 (4)	C10—N4—C11—N5	−0.9 (5)
C10—N3—C7—N2	−12.6 (4)	C10—N4—C11—C12	−179.9 (3)
C10—N3—C7—C8	168.5 (3)	N5—C11—C12—C13	−2.9 (5)
N2—C7—C8—C9	5.7 (5)	N4—C11—C12—C13	176.0 (3)
N3—C7—C8—C9	−175.5 (3)	C11—C12—C13—C14	0.5 (5)
C7—C8—C9—C5	−1.4 (5)	C18—C14—C13—C12	−176.5 (3)
C4—C5—C9—C8	178.9 (3)	C15—C14—C13—C12	1.5 (4)
C6—C5—C9—C8	−2.8 (4)	C11—N4—C10—N3	74.2 (4)
C15—N6—C16—C17	−1.9 (4)	C7—N3—C10—N4	85.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6i	0.88 (4)	1.92	2.794 (4)	168
N3—H3A···O3	0.80 (3)	2.23	2.990 (6)	159
N4—H4A···O5i	0.71 (4)	2.56	3.233 (5)	160
N4—H4A···O7i	0.71 (4)	2.52	3.133 (5)	145
N6—H6···O1	0.84 (3)	2.00	2.838 (8)	178
C1—H1A···O7ii	0.98	2.54	3.501 (3)	167
C1—H1B···O4iii	0.98	2.33	3.078 (4)	132
C4—H4···O8iv	0.95	2.52	3.392 (7)	152
C10—H10B···O4iv	0.99	2.35	3.082 (5)	130
C13—H13···O2i	0.95	2.41	3.259 (3)	149
C19—H19B···O5	0.98	2.57	3.351 (6)	136
C19—H19C···O7v	0.98	2.58	3.207 (7)	122
C19—H19C···O8v	0.98	2.57	3.548 (4)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6i	0.88 (4)	1.92	2.794 (4)	168
N3—H3A⋯O3	0.80 (3)	2.23	2.990 (6)	159
N4—H4A⋯O5i	0.71 (4)	2.56	3.233 (5)	160
N4—H4A⋯O7i	0.71 (4)	2.52	3.133 (5)	145
N6—H6⋯O1	0.84 (3)	2.00	2.838 (8)	178
C1—H1A⋯O7ii	0.98	2.54	3.501 (3)	167
C1—H1B⋯O4iii	0.98	2.33	3.078 (4)	132
C4—H4⋯O8iv	0.95	2.52	3.392 (7)	152
C10—H10B⋯O4iv	0.99	2.35	3.082 (5)	130
C13—H13⋯O2i	0.95	2.41	3.259 (3)	149
C19—H19B⋯O5	0.98	2.57	3.351 (6)	136
C19—H19C⋯O7v	0.98	2.58	3.207 (7)	122
C19—H19C⋯O8v	0.98	2.57	3.548 (4)	172

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