Bis(7,10-dichloro-2-methoxy­benzo[b][1,5]naphthyridinium) chloride perchlorate

Wang, W.

doi:10.1107/S1600536807033193

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Bis(7,10-dichloro-2-methoxybenzo[b][1,5]naphthyridinium) chloride perchlorate

W. Wang

The asymmetric unit of the title compound, 2C₁₃H₉Cl₂N₂O⁺·Cl⁻·ClO₄⁻, contains two cations, one chloride ion and one perchlorate ion. Intermolecular N—H

Cl hydrogen bonds link the cations and anions to form clusters of two cations and a chloride anion. In the crystal packing, the ClO₄⁻ anions bridge neighboring clusters to form a three-dimensional network structure. The relatively short distances Cg1

Cg1ⁱ of 3.664 (3) Å [where Cg1 is the centroid of the central six-membered ring of the organic cation and (i) is 1 − x, 1 − y, 1 − z] are indicative of weak π

π interactions contributing to the stabilization of the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033193/im2024sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033193/im2024Isup2.hkl Contains datablock I

CCDC reference: 657713

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (Wave) = 0.000 Å
R factor = 0.052
wR factor = 0.125
Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C26 H18 Cl6 N4 O6
            Atom count from _chemical_formula_moiety:C26 H18 Cl5 N4 O6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

During the last 20–30 years a large number of derivatives belonging to the general class of anilinoacridines have been prepared and evaluated extensively as antimalarial, antileishmanial, antitrypanosomal and anticancer agents (Anderson, et al., 2006; Ferlin, et al., 2000; Gamage, et al., 1994). Herein we report the crystal structure of the title compound (I) which is the main precursor used to synthesize anilinoacridine derivatives.

The crystal data show that in the title compound, (C₁₃H₉Cl₂N₂O)₂(Cl)(ClO₄), the asymmetric unit of (I) contains two identical cations as well as one Cl^- and one ClO₄^- anion as counter anions. Intermolecular hydrogen bonds [N2—H2A···Cl6; N4—H4A···Cl6] link them to form a dimer (Fig. 1). In the crystal packing the ClO₄^- anion plays an important role linking neighboring dimers to form a three-dimensional network structure (Fig.2). Relatively short Cg1···Cg1ⁱ distances of 3.664 (3) Å [Cg1 is the centroid of ring A (N2/C4/C5/C10/C11/C12)] are indicative of weak π···π interactions contributing to the stabilization of the crystal packing [symmetry codes: (i) 1 - x,1 - y,1 - z].

Related literature top

For a large number of derivatives belonging to the general class of anilinoacridines see: Anderson et al. (2006); Ferlin et al. (2000) and Gamage et al. (1994).

Experimental top

2,4-dichlorobenzoic acid (1 mmol) and 6-methoxypyridin-3-amine (1 mmol, 0.124 g) in 40 ml 2-propanol were refluxed at 140°C for 3 h affording a pale yellow precipitate. By filtering the solution we obtained the intermediate ready for the next step (Anderson et al., 2006). The intermediate was then reacted with PCl₃ at 80°C for additional 3 h. Then the solution was poured into ice water affording a yellow precipitate. After being cooled down to room temperature, the solution was filtered. The yellow solids were washed with water and finally recrystallized from acetone yielding block shaped colorless crystals of compound I.

Structure description top

For a large number of derivatives belonging to the general class of anilinoacridines see: Anderson et al. (2006); Ferlin et al. (2000) and Gamage et al. (1994).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of the asymmetric unit, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. All the H atoms except H9, H15, H16 and H22 have been omitted for clarity.
	Fig. 2. View of the intermolecular hydrogen bonds and weak π···π interactions down c axis [symmetry codes: (i) 1 - x,1 - y,1 - z; (ii) -3/2 + x,1/2 - y,-1/2 + x].

Bis(7,10-dichloro-2-methoxybenzo[b][1,5]naphthyridinium) chloride perchlorate top

Crystal data top

2C₁₃H₉Cl₂N₂O⁺·Cl⁻·ClO₄⁻	F(000) = 1408
M_r = 695.14	D_x = 1.589 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2483 reflections
a = 7.944 (1) Å	θ = 2.6–20.8°
b = 33.972 (5) Å	µ = 0.64 mm⁻¹
c = 11.292 (2) Å	T = 291 K
β = 107.511 (2)°	Block, colourless
V = 2905.9 (7) Å³	0.30 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5707 independent reflections
Radiation source: sealed tube	4631 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
T_min = 0.83, T_max = 0.86	k = −33→41
15872 measured reflections	l = −13→12

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.05P)² + 1.99P] where P = (F_o² + 2F_c²)/3
5707 reflections	(Δ/σ)_max < 0.001
387 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

2C₁₃H₉Cl₂N₂O⁺·Cl⁻·ClO₄⁻	V = 2905.9 (7) Å³
M_r = 695.14	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.944 (1) Å	µ = 0.64 mm⁻¹
b = 33.972 (5) Å	T = 291 K
c = 11.292 (2) Å	0.30 × 0.26 × 0.24 mm
β = 107.511 (2)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5707 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4631 reflections with I > 2σ(I)
T_min = 0.83, T_max = 0.86	R_int = 0.033
15872 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.22 e Å⁻³
5707 reflections	Δρ_min = −0.23 e Å⁻³
387 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	0.6140 (5)	0.43021 (10)	0.7364 (3)	0.0539 (8)
C2	0.5768 (5)	0.40037 (10)	0.6408 (3)	0.0554 (8)
H2	0.6354	0.3763	0.6543	0.067*
C3	0.4540 (4)	0.40846 (10)	0.5306 (3)	0.0540 (8)
H3	0.4294	0.3903	0.4660	0.065*
C4	0.3638 (4)	0.44505 (9)	0.5156 (3)	0.0462 (7)
C5	0.1587 (4)	0.48925 (9)	0.3868 (3)	0.0471 (7)
C6	0.0365 (4)	0.49704 (10)	0.2711 (3)	0.0531 (8)
H6	0.0114	0.4782	0.2083	0.064*
C7	−0.0445 (4)	0.53268 (11)	0.2525 (3)	0.0564 (9)
C8	−0.0108 (4)	0.56188 (10)	0.3500 (3)	0.0527 (8)
H8	−0.0716	0.5857	0.3352	0.063*
C9	0.1064 (4)	0.55524 (9)	0.4609 (3)	0.0497 (7)
H9	0.1270	0.5744	0.5226	0.060*
C10	0.2016 (4)	0.51805 (9)	0.4853 (3)	0.0466 (7)
C11	0.3271 (4)	0.50868 (9)	0.5972 (3)	0.0492 (7)
C12	0.4115 (4)	0.47234 (9)	0.6160 (3)	0.0437 (7)
C13	0.7692 (5)	0.44844 (12)	0.9444 (3)	0.0644 (10)
H13A	0.6603	0.4546	0.9606	0.097*
H13B	0.8189	0.4720	0.9221	0.097*
H13C	0.8503	0.4372	1.0175	0.097*
C14	0.4137 (5)	0.22930 (10)	0.3372 (3)	0.0539 (8)
C15	0.4782 (5)	0.26862 (11)	0.3520 (3)	0.0571 (8)
H15	0.5966	0.2737	0.3927	0.068*
C16	0.3658 (5)	0.29848 (12)	0.3065 (3)	0.0612 (9)
H16	0.4029	0.3246	0.3140	0.073*
C17	0.1844 (4)	0.28774 (10)	0.2453 (3)	0.0495 (7)
C18	−0.1062 (4)	0.30885 (10)	0.1355 (3)	0.0512 (8)
C19	−0.2228 (5)	0.34054 (10)	0.0994 (3)	0.0546 (8)
H19	−0.1847	0.3665	0.1143	0.066*
C20	−0.3982 (5)	0.33131 (11)	0.0402 (4)	0.0609 (9)
C21	−0.4638 (5)	0.29252 (11)	0.0251 (3)	0.0569 (8)
H21	−0.5826	0.2878	−0.0149	0.068*
C22	−0.3486 (5)	0.26132 (11)	0.0709 (4)	0.0621 (9)
H22	−0.3908	0.2356	0.0633	0.075*
C23	−0.1634 (5)	0.26903 (10)	0.1302 (3)	0.0513 (8)
C24	−0.0407 (5)	0.23928 (10)	0.1797 (3)	0.0579 (9)
C25	0.1374 (5)	0.24841 (10)	0.2374 (3)	0.0499 (7)
C26	0.4847 (5)	0.16054 (10)	0.3696 (3)	0.0571 (8)
H26A	0.3919	0.1557	0.4060	0.086*
H26B	0.5838	0.1440	0.4086	0.086*
H26C	0.4431	0.1548	0.2824	0.086*
Cl1	−0.19461 (12)	0.54375 (3)	0.11131 (9)	0.0644 (3)
Cl2	0.38505 (13)	0.54239 (3)	0.71456 (9)	0.0647 (3)
Cl3	−0.54565 (12)	0.36936 (3)	−0.01420 (9)	0.0651 (3)
Cl4	−0.10915 (12)	0.19125 (3)	0.16924 (9)	0.0628 (2)
Cl5	0.88340 (11)	0.34019 (2)	0.45436 (8)	0.0549 (2)
Cl6	0.17575 (11)	0.40244 (3)	0.18450 (8)	0.0579 (2)
N1	0.5355 (4)	0.46412 (8)	0.7254 (2)	0.0480 (6)
N2	0.2435 (4)	0.45403 (8)	0.4072 (3)	0.0478 (6)
H2A	0.219 (5)	0.4369 (11)	0.348 (3)	0.057*
N3	0.2544 (4)	0.21900 (8)	0.2831 (3)	0.0550 (7)
N4	0.0660 (4)	0.31670 (9)	0.1966 (3)	0.0519 (7)
H4A	0.101 (5)	0.3408 (11)	0.205 (3)	0.062*
O3	0.7353 (3)	0.41992 (7)	0.8414 (2)	0.0629 (6)
O4	0.9062 (4)	0.33980 (8)	0.5734 (2)	0.0685 (7)
O5	0.5383 (3)	0.20162 (8)	0.3877 (2)	0.0626 (6)
O6	1.0101 (4)	0.36333 (7)	0.4258 (2)	0.0676 (7)
O7	0.7177 (3)	0.35640 (8)	0.4075 (2)	0.0712 (8)
O8	0.8922 (3)	0.30120 (7)	0.4116 (2)	0.0567 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.055 (2)	0.056 (2)	0.0471 (18)	−0.0052 (16)	0.0096 (15)	0.0004 (15)
C2	0.064 (2)	0.0474 (18)	0.0551 (19)	−0.0029 (15)	0.0187 (16)	−0.0069 (15)
C3	0.0476 (18)	0.0488 (18)	0.059 (2)	0.0046 (14)	0.0056 (15)	−0.0055 (15)
C4	0.0393 (16)	0.0394 (16)	0.0562 (18)	−0.0064 (12)	0.0085 (14)	−0.0083 (14)
C5	0.0395 (16)	0.0426 (17)	0.0602 (19)	0.0011 (13)	0.0167 (14)	−0.0054 (14)
C6	0.0460 (18)	0.0544 (19)	0.0561 (19)	0.0122 (14)	0.0112 (15)	0.0081 (15)
C7	0.0414 (18)	0.062 (2)	0.059 (2)	0.0038 (15)	0.0043 (15)	0.0140 (17)
C8	0.0513 (19)	0.0474 (18)	0.061 (2)	−0.0017 (14)	0.0188 (16)	0.0103 (15)
C9	0.0568 (19)	0.0342 (15)	0.0593 (19)	−0.0016 (13)	0.0193 (16)	0.0084 (14)
C10	0.0489 (18)	0.0340 (15)	0.0600 (19)	−0.0065 (13)	0.0212 (15)	−0.0028 (13)
C11	0.0505 (18)	0.0419 (17)	0.0517 (18)	−0.0069 (14)	0.0101 (14)	−0.0054 (14)
C12	0.0446 (17)	0.0432 (16)	0.0465 (17)	−0.0086 (13)	0.0184 (13)	−0.0057 (13)
C13	0.055 (2)	0.065 (2)	0.063 (2)	0.0072 (17)	0.0019 (17)	−0.0048 (18)
C14	0.0507 (19)	0.057 (2)	0.0524 (19)	0.0038 (15)	0.0128 (15)	0.0017 (15)
C15	0.0501 (19)	0.062 (2)	0.054 (2)	−0.0067 (16)	0.0079 (15)	−0.0010 (16)
C16	0.060 (2)	0.064 (2)	0.059 (2)	−0.0079 (18)	0.0166 (17)	−0.0032 (17)
C17	0.0500 (18)	0.0475 (18)	0.0536 (19)	−0.0093 (14)	0.0194 (15)	−0.0120 (14)
C18	0.0525 (19)	0.0485 (18)	0.0573 (19)	−0.0027 (14)	0.0237 (16)	−0.0104 (15)
C19	0.058 (2)	0.0535 (19)	0.057 (2)	−0.0020 (16)	0.0251 (16)	−0.0129 (16)
C20	0.054 (2)	0.059 (2)	0.071 (2)	0.0121 (16)	0.0199 (18)	−0.0052 (18)
C21	0.053 (2)	0.062 (2)	0.0509 (19)	0.0007 (16)	0.0082 (15)	−0.0106 (16)
C22	0.055 (2)	0.055 (2)	0.071 (2)	−0.0099 (16)	0.0108 (17)	−0.0195 (18)
C23	0.057 (2)	0.0504 (19)	0.0482 (18)	−0.0100 (15)	0.0176 (15)	−0.0142 (14)
C24	0.066 (2)	0.0466 (19)	0.060 (2)	−0.0155 (16)	0.0166 (17)	−0.0145 (15)
C25	0.058 (2)	0.0487 (18)	0.0430 (17)	−0.0003 (15)	0.0148 (14)	−0.0057 (14)
C26	0.055 (2)	0.053 (2)	0.060 (2)	0.0063 (15)	0.0106 (16)	−0.0039 (16)
Cl1	0.0581 (5)	0.0611 (5)	0.0603 (5)	0.0229 (4)	−0.0031 (4)	0.0164 (4)
Cl2	0.0639 (6)	0.0605 (5)	0.0655 (5)	−0.0015 (4)	0.0132 (4)	−0.0174 (4)
Cl3	0.0613 (5)	0.0599 (5)	0.0729 (6)	0.0212 (4)	0.0183 (4)	−0.0141 (4)
Cl4	0.0583 (5)	0.0550 (5)	0.0700 (6)	−0.0195 (4)	0.0115 (4)	−0.0077 (4)
Cl5	0.0589 (5)	0.0539 (5)	0.0546 (5)	0.0103 (4)	0.0213 (4)	−0.0095 (4)
Cl6	0.0565 (5)	0.0559 (5)	0.0556 (5)	0.0088 (4)	0.0082 (4)	0.0090 (4)
N1	0.0489 (15)	0.0534 (16)	0.0408 (14)	−0.0068 (12)	0.0119 (12)	−0.0074 (11)
N2	0.0470 (15)	0.0439 (15)	0.0495 (15)	0.0007 (11)	0.0100 (12)	−0.0003 (12)
N3	0.0542 (17)	0.0493 (16)	0.0591 (17)	0.0002 (13)	0.0133 (13)	−0.0021 (13)
N4	0.0541 (17)	0.0540 (17)	0.0455 (15)	−0.0056 (13)	0.0119 (12)	−0.0108 (13)
O3	0.0684 (16)	0.0528 (14)	0.0554 (14)	0.0090 (12)	0.0001 (12)	0.0033 (11)
O4	0.0756 (18)	0.0705 (17)	0.0610 (16)	0.0110 (13)	0.0229 (13)	−0.0152 (13)
O5	0.0537 (14)	0.0634 (15)	0.0628 (15)	0.0107 (12)	0.0056 (11)	0.0031 (12)
O6	0.0681 (16)	0.0607 (16)	0.0749 (17)	−0.0193 (13)	0.0228 (13)	−0.0239 (13)
O7	0.0613 (15)	0.0619 (15)	0.0660 (16)	0.0168 (12)	−0.0176 (12)	−0.0235 (12)
O8	0.0597 (14)	0.0455 (12)	0.0626 (14)	0.0144 (10)	0.0148 (11)	−0.0057 (11)

Geometric parameters (Å, º) top

C1—N1	1.298 (4)	C15—H15	0.9300
C1—O3	1.330 (4)	C16—C17	1.445 (5)
C1—C2	1.445 (5)	C16—H16	0.9300
C2—C3	1.358 (5)	C17—N4	1.358 (4)
C2—H2	0.9300	C17—C25	1.383 (4)
C3—C4	1.419 (4)	C18—N4	1.360 (4)
C3—H3	0.9300	C18—C19	1.398 (5)
C4—N2	1.342 (4)	C18—C23	1.422 (5)
C4—C12	1.424 (4)	C19—C20	1.388 (5)
C5—N2	1.358 (4)	C19—H19	0.9300
C5—C6	1.399 (5)	C20—C21	1.408 (5)
C5—C10	1.442 (4)	C20—Cl3	1.728 (4)
C6—C7	1.358 (5)	C21—C22	1.394 (5)
C6—H6	0.9300	C21—H21	0.9300
C7—C8	1.445 (5)	C22—C23	1.445 (5)
C7—Cl1	1.721 (3)	C22—H22	0.9300
C8—C9	1.336 (5)	C23—C24	1.399 (5)
C8—H8	0.9300	C24—C25	1.402 (5)
C9—C10	1.456 (4)	C24—Cl4	1.713 (3)
C9—H9	0.9300	C25—N3	1.356 (4)
C10—C11	1.391 (5)	C26—O5	1.455 (4)
C11—C12	1.390 (4)	C26—H26A	0.9600
C11—Cl2	1.707 (3)	C26—H26B	0.9600
C12—N1	1.357 (4)	C26—H26C	0.9600
C13—O3	1.475 (4)	Cl5—O4	1.301 (3)
C13—H13A	0.9600	Cl5—O7	1.377 (2)
C13—H13B	0.9600	Cl5—O6	1.389 (3)
C13—H13C	0.9600	Cl5—O8	1.419 (2)
C14—N3	1.278 (4)	Cl6—N2	2.978 (3)
C14—O5	1.359 (4)	Cl6—N4	3.055 (3)
C14—C15	1.422 (5)	N2—H2A	0.86 (4)
C15—C16	1.347 (5)	N4—H4A	0.86 (4)

N1—C1—O3	121.1 (3)	C25—C17—C16	119.1 (3)
N1—C1—C2	124.5 (3)	N4—C18—C19	118.3 (3)
O3—C1—C2	114.3 (3)	N4—C18—C23	117.9 (3)
C3—C2—C1	118.1 (3)	C19—C18—C23	123.0 (3)
C3—C2—H2	120.9	C20—C19—C18	116.6 (3)
C1—C2—H2	120.9	C20—C19—H19	121.7
C2—C3—C4	119.0 (3)	C18—C19—H19	121.7
C2—C3—H3	120.5	C19—C20—C21	123.4 (3)
C4—C3—H3	120.5	C19—C20—Cl3	118.5 (3)
N2—C4—C3	120.2 (3)	C21—C20—Cl3	118.1 (3)
N2—C4—C12	121.6 (3)	C22—C21—C20	119.3 (3)
C3—C4—C12	118.1 (3)	C22—C21—H21	120.4
N2—C5—C6	119.6 (3)	C20—C21—H21	120.4
N2—C5—C10	118.5 (3)	C21—C22—C23	119.8 (3)
C6—C5—C10	121.9 (3)	C21—C22—H22	120.1
C7—C6—C5	118.5 (3)	C23—C22—H22	120.1
C7—C6—H6	120.8	C24—C23—C18	119.7 (3)
C5—C6—H6	120.8	C24—C23—C22	123.0 (3)
C6—C7—C8	121.6 (3)	C18—C23—C22	117.4 (3)
C6—C7—Cl1	120.1 (3)	C23—C24—C25	120.7 (3)
C8—C7—Cl1	118.3 (3)	C23—C24—Cl4	119.5 (3)
C9—C8—C7	121.0 (3)	C25—C24—Cl4	119.9 (3)
C9—C8—H8	119.5	N3—C25—C17	123.1 (3)
C7—C8—H8	119.5	N3—C25—C24	119.6 (3)
C8—C9—C10	120.0 (3)	C17—C25—C24	117.3 (3)
C8—C9—H9	120.0	O5—C26—H26A	109.5
C10—C9—H9	120.0	O5—C26—H26B	109.5
C11—C10—C5	118.9 (3)	H26A—C26—H26B	109.5
C11—C10—C9	124.1 (3)	O5—C26—H26C	109.5
C5—C10—C9	117.0 (3)	H26A—C26—H26C	109.5
C12—C11—C10	121.5 (3)	H26B—C26—H26C	109.5
C12—C11—Cl2	118.2 (2)	O4—Cl5—O7	102.72 (17)
C10—C11—Cl2	120.3 (2)	O4—Cl5—O6	111.11 (18)
N1—C12—C11	120.4 (3)	O7—Cl5—O6	111.09 (19)
N1—C12—C4	122.5 (3)	O4—Cl5—O8	109.67 (16)
C11—C12—C4	117.1 (3)	O7—Cl5—O8	112.46 (15)
O3—C13—H13A	109.5	O6—Cl5—O8	109.63 (15)
O3—C13—H13B	109.5	N2—Cl6—N4	120.32 (8)
H13A—C13—H13B	109.5	C1—N1—C12	117.8 (3)
O3—C13—H13C	109.5	C4—N2—C5	122.4 (3)
H13A—C13—H13C	109.5	C4—N2—Cl6	122.3 (2)
H13B—C13—H13C	109.5	C5—N2—Cl6	114.9 (2)
N3—C14—O5	120.2 (3)	C4—N2—H2A	119 (2)
N3—C14—C15	125.7 (3)	C5—N2—H2A	119 (2)
O5—C14—C15	114.2 (3)	C14—N3—C25	116.5 (3)
C16—C15—C14	119.3 (3)	C17—N4—C18	122.1 (3)
C16—C15—H15	120.4	C17—N4—Cl6	122.5 (2)
C14—C15—H15	120.4	C18—N4—Cl6	114.9 (2)
C15—C16—C17	116.3 (3)	C17—N4—H4A	119 (3)
C15—C16—H16	121.8	C18—N4—H4A	119 (3)
C17—C16—H16	121.8	C1—O3—C13	116.2 (3)
N4—C17—C25	122.2 (3)	C14—O5—C26	117.3 (3)
N4—C17—C16	118.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl6	0.86 (4)	2.13 (4)	2.978 (3)	169 (3)
N4—H4A···Cl6	0.86 (4)	2.21 (4)	3.055 (3)	169 (3)
C9—H9···O6ⁱ	0.93	2.53	3.295 (4)	140
C9—H9···O7ⁱ	0.93	2.66	3.453 (4)	143
C22—H22···O8ⁱⁱ	0.93	2.39	3.124 (4)	136
C15—H15···O8	0.93	2.48	3.341 (4)	155
C16—H16···O7	0.93	2.64	3.327 (5)	132

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

Experimental details

Crystal data
Chemical formula	2C₁₃H₉Cl₂N₂O⁺·Cl⁻·ClO₄⁻
M_r	695.14
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	7.944 (1), 33.972 (5), 11.292 (2)
β (°)	107.511 (2)
V (Å³)	2905.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.30 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.83, 0.86
No. of measured, independent and observed [I > 2σ(I)] reflections	15872, 5707, 4631
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.125, 1.09
No. of reflections	5707
No. of parameters	387
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl6	0.86 (4)	2.13 (4)	2.978 (3)	169 (3)
N4—H4A···Cl6	0.86 (4)	2.21 (4)	3.055 (3)	169 (3)
C9—H9···O6ⁱ	0.93	2.53	3.295 (4)	140
C9—H9···O7ⁱ	0.93	2.66	3.453 (4)	143
C22—H22···O8ⁱⁱ	0.93	2.39	3.124 (4)	136
C15—H15···O8	0.93	2.48	3.341 (4)	155
C16—H16···O7	0.93	2.64	3.327 (5)	132

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

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