Bis(2-amino-6-methyl­pyridinium) di-μ-chlorido-μ-oxido-bis­[dichlorido­antimonate(III)]

The title compound, (C₆H₉N₂)₂[Sb₂Cl₆O], consists of one triple-bridged [Sb₂Cl₆O]²⁻ anion and two 2-amino-6-methyl­pyridinium cations that undergo aminium–iminium tautomerism. The counter-ion pair are linked together by N—H...O and N—H...Cl hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.047
• wR factor = 0.095
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.08 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        Sb2

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT245_ALERT_2_C U(iso) H1N     Smaller than U(eq) N1      by ...       0.02 AngSq
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         11
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C12
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl6    ..  O1      ..       3.15 Ang.
PLAT731_ALERT_1_C Bond    Calc   3.3555(7), Rep    3.355(2) ......       2.86 su-Ra
              SB2  -SB1     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.836(19) ......       2.11 su-Ra
              N1   -H1N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(5), Rep     0.85(2) ......       2.50 su-Ra
              N3   -H3N     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(4), Rep   0.835(19) ......       2.11 su-Ra
              N2   -H2A     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(5), Rep   0.837(19) ......       2.63 su-Ra
              N2   -H2B     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.84(6), Rep     0.85(2) ......       3.00 su-Ra
              N4   -H4A     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(5), Rep     0.84(2) ......       2.50 su-Ra
              N2   -H2B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(5), Rep     0.85(2) ......       2.50 su-Ra
              N3   -H3N     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(6), Rep     0.85(2) ......       3.00 su-Ra
              N4   -H4A     1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C6 H9 N2

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Sb1         (3)       3.03
PLAT794_ALERT_5_G Check Predicted Bond Valency for Sb2         (3)       3.03
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          8

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

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

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S1. Comment

There are numerous examples of 2-amino-substituted pyridine compounds reported previously (Navarro Ranninger et al., 1985; Krizanovic et al., 1993; Luque et al., 1997; Qin et al., 1999; Yip et al., 1999; Lah et al., 2002; Ren et al., 2002; Rivas et al., 2003; Jin et al., 2000, 2001, 2002, 2005; Albrecht et al., 2003). Among them, the tautomerism phenominon (Scheme 1) of 2-amino-X-methylpyridine [2AXMP; X indicates the methyl position] has been proved by X-ray diffraction, such as 2 A6MP-hydrochloric acid (2/2; Jin et al., 2005) and 2 A6MP-neoabietic acid (1/1; Jin et al., 2000). All the above studies provide important references to futher research into 2-aminopyridines. Now, the title compound, (I), has been sythesized, as a continue part of research.

As shown in Fig. 1, there are two crystallographically independent 2-amino-6-methylpyridinium (HAMP) cations and a (Sb₂Cl₆O)^2- anion in the formula unit. The anion is linked to one HAMP (N1/N2/C1/C6) by N1—H1N···O1 and N2—H2A···Cl4 hydrogen bonds, and to the other HAMP(N3/N4/C7/C12) by N3—H3N···Cl6 hydrogen bond.

In the structure, two 2-amino-6-methylpyridine molecules are protonated, and show aminium-iminium tautomerism phenominon (Inuzuka & Fujimoto, 1986 and 1990). Features of the iminium tautomer are most clearly observed in (I), suggesting that the imime tautomer play a important role in the structure. In cation HAMP (N1/N2/C1/C6), the N2—C1 bond [1.329 (8) Å] is a little but significantly shorter than the N1—C1 [1.353 (8) Å] and N1—C5 [1.353 (8) Å] bonds, coincident with the iminium tautomer (Table 1). Moreover, the existence of the iminium tautomer is testified by the fact that the C1—C2 [1.389 (9) Å] and C3—C4 [1.387 (10) Å] bonds are longer than the C2—C3 [1.343 (9) Å] and C4—C5 [1.350 (9) Å] bonds. Similar features are provided with HAMP (N3/N4/C7/C12). In the HAMP (N3/N4/C7/C12), the N4 and three H atoms of N3 and N4 are on the same plane with the matrix heterocycle. But, there is a slight difference in the cation HAMP (N1/N2/C1/C6). H2A of N2 deviates from the matrix plane at a distance of 0.2507 (8) Å, due to N2—H2A···Cl4 hydrogen bond (Fig. 1).

The structure of the (Sb₂Cl₆O)^2- anion resembles a anionic antimony(III) oxide chloride reported previously (Hall & Sowerby, 1979). It has a discrete dimeric structure resulting from the sharing of a common face between two pseudo-octahedral units. The triple bridge involves one oxygen (O1) and two chlorine atoms (Cl3 and Cl6). The structure is based on two SbOCl₄ pseudo-octahedral units. The lone pair of electrons of Sb in each case occupies the sixth octahedral posotion which is trans to the bridging oxygen atom. Bonds to terminal chlorine atoms are of normal length and are substantially shorter than those involving in bridging (Table. 1). Bridging is asymmmetrical at Cl3 but both Cl6 and O1 form symmetrical bridges. The distance between Sb1 and Sb2 is of 3.530 (8) Å, a value well within the sum of van der Waals' radius (4.4 Å).

In the structure, the Sb₂Cl₆O entities link to their neighbouring ones through coordinated bonds of Sb1—Cl5 (-x + 1/2, y + 1/2, -z + 1/2) [3.530 (8) Å] in chains (Fig. 2). The chains link to their antiparallel neighbouring ones by Sb2—Cl3 (-x, -y + 2, -z) coordinated bonds [3.481 (8) Å]. Every two corresponding Sb₂Cl₆O entities in the two antiparallel neighbouring chains submit centrosymmetrically. The whole crystal structure is formed by extensive network of moderate intermolecular hydrogen bonds of N4—H4A···Cl6, N2—H2B···Cl3 (-x + 1, -y + 2, -z), N4—H4B^···Cl2 (-x + 1, -y + 2, -z) and N4—H4b···Cl1 (-x + 1, -y + 2, -z), including the above three strong intromolecular hydrogen bonds and coordinated Sb—Cl bonds (Fig. 3).

Related literature

For related literature, see: Albrecht et al. (2003); Jin et al. (2001, 2002, 2000, 2005); Krizanovic et al. (1993); Lah et al. (2002); Luque et al. (1997); Hall & Sowerby (1979); Navarro et al. (1985); Qin et al. (1999); Ren et al. (2002); Rivas et al. (2003); Yip et al. (1999); Inuzuka & Fujimoto (1986, 1990).

S2. Experimental

The preparation of the single-crystal of (I): dissolving 1.5 g antimony trichloride in 10 ml absolute acetone to form a solution, then adding 1 ml hydrochloride acid and 2 ml 2-amino-6-methylpyridine to the solution. Keeping stir and heating, until it became a clear solution, then the reaction system was cooled slowly to room temperature. Crystals of (I) were formed by gradual evaporation of the acetone over a period of three days at 300 K. Analysis calculated for Sb₂Cl₆O(C₆H₉N₂)₂: C 20.33, H 2.42, N 7.90%. Found: C 20.28, H 2.45, N 7.97%.

S3. Refinement

H atoms attaching to N atoms were deduced from difference Fourier maps, and incorporated in refinement freely. Others were placed in calculated positions and allowed to ride on their parent atoms at distances of 0.93Å for aromatic group and 0.96Å for methyl, with U_iso(H) = 1.2–1.5 U_eq(C).

Computing details

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: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I), 30% probability displacement ellipsoids is shown. Hydrogn bonds are illustrated as dashed lines.
	Fig. 2. The packing diagram of Sb2Cl6O anions viewed down along the c axis.
	Fig. 3. The packing diagram of (I) viewed down along the a axis. Hydrogen bonds are illustrated by dashed lines.
	Fig. 4. The tautomerism in the 2-amino-6-methylpyridinium cation.

Bis(2-amino-6-methylpyridinium) di-µ-chlorido-µ-oxido-bis[dichloridoantimonate(III)]

Crystal data

(C6H9N2)2[Sb2Cl6O]	F(000) = 1320.0
Mr = 690.52	Dx = 1.978 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5386 reflections
a = 10.0746 (10) Å	θ = 2.2–24.9°
b = 15.1972 (16) Å	µ = 3.03 mm^−1
c = 15.4631 (14) Å	T = 298 K
β = 101.597 (6)°	Block, colourless
V = 2319.2 (4) Å^3	0.30 × 0.30 × 0.30 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	4154 independent reflections
Radiation source: fine-focus sealed tube	3876 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→8
Tmin = 0.419, Tmax = 0.419	k = −18→18
12055 measured reflections	l = −17→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.24	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 5.7532P] where P = (Fo^2 + 2Fc^2)/3
4137 reflections	(Δ/σ)max < 0.001
250 parameters	Δρmax = 0.86 e Å^−3
8 restraints	Δρmin = −0.50 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Sb1	0.31762 (4)	0.91360 (3)	0.22353 (3)	0.03853 (13)
Sb2	0.11872 (4)	1.06417 (3)	0.10221 (3)	0.03951 (13)
Cl5	0.1190 (2)	1.20568 (13)	0.17485 (18)	0.0883 (7)
Cl4	0.2383 (2)	1.12353 (18)	−0.00553 (15)	0.0899 (8)
Cl6	0.0414 (2)	0.96108 (14)	0.24743 (13)	0.0676 (5)
Cl2	0.52714 (18)	0.90105 (13)	0.17034 (12)	0.0612 (5)
Cl3	0.17591 (17)	0.88522 (11)	0.04966 (10)	0.0502 (4)
Cl1	0.44172 (18)	0.96909 (13)	0.36800 (11)	0.0607 (5)
O1	0.2946 (4)	1.0349 (2)	0.1794 (3)	0.0369 (9)
N1	0.5322 (5)	1.1474 (3)	0.1987 (4)	0.0428 (12)
N3	−0.0424 (6)	1.0719 (4)	0.3982 (4)	0.0530 (14)
N2	0.5688 (7)	1.0906 (5)	0.0664 (4)	0.0653 (18)
C1	0.6139 (6)	1.1355 (4)	0.1402 (4)	0.0440 (15)
C5	0.5662 (7)	1.1973 (4)	0.2724 (4)	0.0476 (16)
N4	−0.2302 (7)	0.9894 (6)	0.3401 (5)	0.079 (2)
C7	−0.1687 (7)	1.0454 (5)	0.4007 (5)	0.0534 (17)
C11	0.0303 (8)	1.1289 (5)	0.4562 (5)	0.063 (2)
C6	0.4618 (8)	1.2076 (5)	0.3281 (5)	0.065 (2)
H6A	0.3829	1.1737	0.3032	0.098*
H6B	0.4374	1.2685	0.3301	0.098*
H6C	0.4981	1.1871	0.3868	0.098*
C2	0.7428 (7)	1.1720 (5)	0.1600 (5)	0.0546 (17)
H2	0.8037	1.1630	0.1230	0.065*
C8	−0.2278 (8)	1.0787 (5)	0.4684 (5)	0.062 (2)
H8	−0.3149	1.0619	0.4729	0.075*
C3	0.7781 (8)	1.2206 (5)	0.2336 (5)	0.067 (2)
H3	0.8647	1.2446	0.2473	0.081*
C4	0.6893 (8)	1.2359 (5)	0.2898 (5)	0.067 (2)
H4	0.7142	1.2723	0.3388	0.080*
C9	−0.1572 (9)	1.1350 (6)	0.5269 (5)	0.072 (2)
H9	−0.1967	1.1576	0.5716	0.086*
C10	−0.0270 (10)	1.1603 (5)	0.5221 (6)	0.079 (3)
H10	0.0211	1.1985	0.5640	0.094*
C12	0.1683 (9)	1.1504 (6)	0.4414 (7)	0.090 (3)
H12A	0.1840	1.1196	0.3902	0.135*
H12B	0.2347	1.1329	0.4920	0.135*
H12C	0.1750	1.2126	0.4323	0.135*
H1N	0.458 (3)	1.121 (3)	0.191 (3)	0.024 (14)*
H4A	−0.195 (6)	0.970 (5)	0.299 (4)	0.08 (3)*
H3N	−0.008 (6)	1.046 (4)	0.359 (3)	0.046 (19)*
H2A	0.487 (3)	1.076 (4)	0.052 (4)	0.06 (2)*
H2B	0.616 (5)	1.085 (5)	0.028 (3)	0.07 (3)*
H4B	−0.312 (3)	0.975 (5)	0.337 (4)	0.08 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sb1	0.0418 (2)	0.0367 (2)	0.0381 (2)	0.00126 (17)	0.01051 (18)	0.00583 (17)
Sb2	0.0305 (2)	0.0408 (2)	0.0460 (3)	0.00311 (17)	0.00485 (17)	−0.00017 (18)
Cl5	0.0748 (14)	0.0531 (11)	0.128 (2)	0.0129 (10)	−0.0002 (13)	−0.0301 (12)
Cl4	0.0681 (13)	0.1222 (19)	0.0832 (15)	0.0132 (13)	0.0242 (11)	0.0587 (14)
Cl6	0.0643 (12)	0.0844 (13)	0.0647 (12)	−0.0134 (10)	0.0381 (10)	−0.0141 (10)
Cl2	0.0497 (10)	0.0758 (12)	0.0620 (11)	0.0222 (9)	0.0209 (8)	0.0095 (9)
Cl3	0.0538 (10)	0.0551 (9)	0.0421 (9)	−0.0001 (8)	0.0110 (7)	−0.0087 (7)
Cl1	0.0562 (11)	0.0833 (13)	0.0413 (9)	−0.0084 (9)	0.0067 (8)	−0.0003 (9)
O1	0.031 (2)	0.033 (2)	0.044 (2)	−0.0005 (17)	0.0028 (17)	0.0111 (18)
N1	0.036 (3)	0.042 (3)	0.051 (3)	−0.005 (2)	0.012 (3)	−0.003 (3)
N3	0.052 (4)	0.058 (4)	0.052 (4)	0.000 (3)	0.019 (3)	−0.010 (3)
N2	0.056 (4)	0.085 (5)	0.058 (4)	−0.020 (4)	0.018 (3)	−0.024 (4)
C1	0.046 (4)	0.040 (3)	0.047 (4)	−0.005 (3)	0.012 (3)	−0.006 (3)
C5	0.052 (4)	0.042 (3)	0.050 (4)	0.002 (3)	0.014 (3)	−0.008 (3)
N4	0.051 (4)	0.118 (6)	0.071 (5)	−0.021 (4)	0.019 (4)	−0.035 (5)
C7	0.045 (4)	0.067 (5)	0.050 (4)	0.003 (3)	0.015 (3)	0.002 (4)
C11	0.076 (5)	0.047 (4)	0.068 (5)	−0.008 (4)	0.020 (4)	0.003 (4)
C6	0.069 (5)	0.070 (5)	0.063 (5)	0.008 (4)	0.029 (4)	−0.018 (4)
C2	0.043 (4)	0.069 (5)	0.055 (4)	−0.010 (3)	0.016 (3)	−0.013 (4)
C8	0.061 (5)	0.071 (5)	0.060 (5)	0.009 (4)	0.022 (4)	0.001 (4)
C3	0.053 (4)	0.084 (6)	0.068 (5)	−0.027 (4)	0.018 (4)	−0.018 (4)
C4	0.070 (5)	0.071 (5)	0.059 (5)	−0.023 (4)	0.013 (4)	−0.026 (4)
C9	0.093 (6)	0.076 (6)	0.058 (5)	0.013 (5)	0.041 (5)	−0.002 (4)
C10	0.107 (7)	0.063 (5)	0.071 (6)	−0.013 (5)	0.031 (5)	−0.022 (4)
C12	0.087 (6)	0.077 (6)	0.113 (8)	−0.032 (5)	0.037 (6)	−0.016 (5)

Geometric parameters (Å, º)

Sb1—O1	1.964 (4)	N4—H4A	0.85 (2)
Sb1—Cl2	2.4221 (18)	N4—H4B	0.84 (2)
Sb1—Cl1	2.4783 (18)	C7—C8	1.399 (10)
Sb1—Cl3	2.8123 (16)	C11—C10	1.355 (10)
Sb2—O1	1.977 (4)	C11—C12	1.490 (11)
Sb2—Cl4	2.418 (2)	C6—H6A	0.9600
Sb2—Cl5	2.426 (2)	C6—H6B	0.9600
Sb2—Sb1	3.355 (2)	C6—H6C	0.9600
N1—C1	1.353 (8)	C2—C3	1.343 (9)
N1—C5	1.353 (8)	C2—H2	0.9300
N1—H1N	0.836 (19)	C8—C9	1.340 (11)
N3—C7	1.343 (9)	C8—H8	0.9300
N3—C11	1.351 (9)	C3—C4	1.387 (10)
N3—H3N	0.85 (2)	C3—H3	0.9300
N2—C1	1.329 (8)	C4—H4	0.9300
N2—H2A	0.835 (19)	C9—C10	1.383 (12)
N2—H2B	0.837 (19)	C9—H9	0.9300
C1—C2	1.389 (9)	C10—H10	0.9300
C5—C4	1.350 (9)	C12—H12A	0.9600
C5—C6	1.496 (9)	C12—H12B	0.9600
N4—C7	1.323 (9)	C12—H12C	0.9600
O1—Sb1—Cl2	90.35 (12)	N3—C11—C12	115.9 (7)
O1—Sb1—Cl1	89.82 (12)	C10—C11—C12	126.2 (8)
Cl2—Sb1—Cl1	90.96 (7)	C5—C6—H6A	109.5
O1—Sb1—Cl3	79.04 (12)	C5—C6—H6B	109.5
Cl2—Sb1—Cl3	88.44 (6)	H6A—C6—H6B	109.5
Cl1—Sb1—Cl3	168.84 (6)	C5—C6—H6C	109.5
O1—Sb2—Cl4	89.39 (12)	H6A—C6—H6C	109.5
O1—Sb2—Cl5	90.13 (12)	H6B—C6—H6C	109.5
Cl4—Sb2—Cl5	91.95 (10)	C3—C2—C1	118.9 (6)
Sb1—O1—Sb2	116.72 (18)	C3—C2—H2	120.5
C1—N1—C5	123.6 (5)	C1—C2—H2	120.5
C1—N1—H1N	119 (4)	C9—C8—C7	119.2 (8)
C5—N1—H1N	117 (4)	C9—C8—H8	120.4
C7—N3—C11	124.3 (6)	C7—C8—H8	120.4
C7—N3—H3N	114 (4)	C2—C3—C4	122.0 (7)
C11—N3—H3N	122 (5)	C2—C3—H3	119.0
C1—N2—H2A	121 (4)	C4—C3—H3	119.0
C1—N2—H2B	121 (4)	C5—C4—C3	119.0 (7)
H2A—N2—H2B	117 (3)	C5—C4—H4	120.5
N2—C1—N1	119.6 (6)	C3—C4—H4	120.5
N2—C1—C2	122.6 (6)	C8—C9—C10	121.4 (7)
N1—C1—C2	117.8 (6)	C8—C9—H9	119.3
C4—C5—N1	118.6 (6)	C10—C9—H9	119.3
C4—C5—C6	124.3 (6)	C11—C10—C9	119.6 (8)
N1—C5—C6	117.1 (6)	C11—C10—H10	120.2
C7—N4—H4A	124 (4)	C9—C10—H10	120.2
C7—N4—H4B	121 (4)	C11—C12—H12A	109.5
H4A—N4—H4B	115 (3)	C11—C12—H12B	109.5
N4—C7—N3	118.9 (7)	H12A—C12—H12B	109.5
N4—C7—C8	123.6 (7)	C11—C12—H12C	109.5
N3—C7—C8	117.5 (7)	H12A—C12—H12C	109.5
N3—C11—C10	118.0 (7)	H12B—C12—H12C	109.5
Cl2—Sb1—O1—Sb2	127.71 (19)	N2—C1—C2—C3	176.4 (8)
Cl1—Sb1—O1—Sb2	−141.33 (19)	N1—C1—C2—C3	−3.1 (10)
Cl3—Sb1—O1—Sb2	39.36 (17)	N4—C7—C8—C9	179.8 (8)
Cl4—Sb2—O1—Sb1	−128.3 (2)	N3—C7—C8—C9	0.3 (11)
Cl5—Sb2—O1—Sb1	139.7 (2)	C1—C2—C3—C4	−0.6 (13)
C5—N1—C1—N2	−175.3 (7)	N1—C5—C4—C3	−2.4 (11)
C5—N1—C1—C2	4.3 (9)	C6—C5—C4—C3	179.3 (7)
C1—N1—C5—C4	−1.5 (10)	C2—C3—C4—C5	3.4 (13)
C1—N1—C5—C6	177.0 (6)	C7—C8—C9—C10	−0.6 (12)
C11—N3—C7—N4	179.8 (8)	N3—C11—C10—C9	−1.5 (12)
C11—N3—C7—C8	−0.6 (11)	C12—C11—C10—C9	179.3 (8)
C7—N3—C11—C10	1.2 (11)	C8—C9—C10—C11	1.3 (14)
C7—N3—C11—C12	−179.5 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.84 (2)	2.08 (3)	2.907 (8)	169 (3)
N2—H2A···Cl4	0.84 (2)	2.59 (6)	3.329 (8)	148 (3)
N2—H2B···Cl3^i	0.84 (2)	2.67 (6)	3.439 (8)	157 (3)
N3—H3N···Cl6	0.85 (2)	2.30 (5)	3.127 (8)	167 (4)
N4—H4A···Cl6	0.85 (2)	2.66 (3)	3.362 (8)	141 (5)
N4—H4B···Cl1^ii	0.84 (2)	2.62 (3)	3.432 (8)	162 (5)

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