Tetra­kis(2-amino-4-methyl­pyridinium) cyclo-tetra-μ₂-oxido-tetra­kis­[dioxido­vanadate(V)] tetra­hydrate

The asymmetric unit of the title compound, (C₆H₉N₂)₄[V₄O₁₂]·4H₂O, contains half of a [V₄O₁₂]⁴⁻ anion, two 2-amino-4-methyl­pyridinium, (2a4mpH)⁺, cations and two water mol­ecules. One water mol­ecule is disordered over two sets of sites with equal occupancies and the H atoms for this mol­ecule were not included in the refinement. The cation lies on an inversion center with four tetra­hedral VO₄ units each sharing two vertices, forming an eight-membered ring. In the crystal, the components are linked by inter­molecular N—H...O hydrogen bonds, forming a one-dimensional network along [100]. Further stabilization is provided by weak inter­molecular C—H...O hydrogen bonds. In addition, π–π stacking inter­actions with centroid–centroid distances of 3.5420 (18), 3.7577 (18) and 3.6311 (19) Å are observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• H-atom completeness 91%
• Disorder in solvent or counterion
• R factor = 0.044
• wR factor = 0.129
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O6     ..  O8      ..       2.74 Ang.
PLAT430_ALERT_2_B Short Inter D...A Contact  O6     ..  O7      ..       2.80 Ang.

Alert level C
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT041_ALERT_1_C Calc. and Reported SumFormula    Strings  Differ          ?
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....        *O7
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....        *O8
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  O2      ..       2.64 Ang.
PLAT732_ALERT_1_C Angle   Calc     101(10), Rep      102(4) ......       2.50 su-Ra
              H9A  -O9   -H9B     1.555   1.555   1.555      #         69
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         10
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         49
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C24 H44 N8 O16 V4
            Atom count from the _atom_site data:  C24 H40 N8 O16 V4
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    1
           From the CIF: _chemical_formula_sum  C24 H44 N8 O16 V4
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         24.00     24.00    0.00
           H         44.00     40.00    4.00
           N          8.00      8.00    0.00
           O         16.00     16.00    0.00
           V          4.00      4.00    0.00
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          3
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00400 Deg.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT302_ALERT_4_G Note: Anion/Solvent Disorder ...................          6 Perc.
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C6
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C12
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.13 Ratio
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3
PLAT960_ALERT_3_G Number of Intensities with I .LT. - 2*sig(I) ...          2

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
  12 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

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

---

S1. Comment

The chemistry of polyoxovanadate compounds are of great interest. Hybrid organo-inorganic compounds based on vanadium oxides present potential applications in catalysis, electron conductivity, magnetism and photochemistry (Paredes-García et al., 2008). The VO₄ group is an important building block of many polynuclear species. A well known example is the V₄O₁₂^4– ring which has an eight-membered ring structure formed by four VO₄ tetrahedra sharing vertices (Nakano et al., 2002). The complexing ability of the V₄O₁₂^4– ion with transition metal ions is of great interest and the ring takes part as a ligand (Paredes-García et al., 2008). Herein we report the crystal structure of the title compound obtained as a side product from a reaction of ammonium vanadate, cobalt nitrate, boric acid and 2-Amino-4-methylpyridine.

The asymmetric unit of the title compound, (2a4mpH)₄(V₄O₁₂).4H₂O, comprises a half of a V₄O₁₂^4– anion, two (2a4mpH)⁺ cations and two solvent molecules of water (Fig. 1). One molecule of water is disordered over two positions (O7 and O8) with equal occupancies.

The V₄O₁₂^4– ion is centrosymmetric with four tetrahedral VO₄units which share two vertices with each other to form an eight-membered ring. The 2-Amino-4-methylpyridine molecule is protonated via its endocyclic nitrogen atom. In the crystal, extensive intermolecular N—H···O hydrogen-bonding interactions (Table 1) between cations, anions and solvent water molecules form 1-D motive chains along [100] (Fig.2). The crystal packing is defined by a layered structure in which chains involving 2a4mpH⁺ and V₄O₁₂^4– ions are associated via π–π stacking interactions between the aromatic rings of (2a4mpH)⁺ cations into layers parallel to (110) (Fig. 3).

Related literature

For related structures, see: Paredes-García et al. (2008); Nakano et al. (2002).

S2. Experimental

Ammonium vanadate, cobalt nitrate hexahydrate, boric acidand 2-amino-4-methylpyridine (in molar ratio 0.5:1:1:2) were dissolved in H₂O (50ml). The reaction mixture was placed in a Parr-Teflon lined stainless steel vessel. It was sealed and heated at 443K for 48 h. The reaction mixture was gradually cooled to room temperature. Pale yellow crystals were isolated from solution.

S3. Refinement

A water molecule is disordered over two positions (O7 and O8) with equal occupancies. The H atoms for this molecule were not located nor were they included in the refinement. They are however, included in the molecular formula. Hydrogen atoms bound to the water molecule O9 were refined using the following restraints: O—H bond length 0.95 (2) Å and H···H distance 1.50 (4) Å. All other H atoms were placed in calculated positions with C-H = 0.93 - 0.96Å and N-H = 0.86Å and were included in the refinement with U_iso(H) = 1.2U_eq(C, N) or 1.5U_eq(C_methyl)

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. ORTEP-3 drawing of the asymmetric unit of the title compound with displacement ellipsoids drawn at the 50 % proabality leveland hydrogen atoms are depicted as spheres of arbitrary radii. Symmetry operator: (i) 2 - x, -y, 1 - z.
	Fig. 2. A hydrogen-bonded (dotted lines) chain consisting of anions and cations, extending in the direction [100]. The solvent water molecules are not shown.
	Fig. 3. Packing of the title compound viewed along [100] with π–π stacking interactions shown as dashed lines.

Tetrakis(2-amino-4-methylpyridinium) cyclo-tetra-µ₂-oxido-tetrakis[dioxidovanadate(V)] tetrahydrate

Crystal data

(C6H9N2)4[V4O12]·4H2O	Z = 1
Mr = 900.39	F(000) = 332
Triclinic, P1	Dx = 1.557 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54179 Å
a = 7.8739 (3) Å	Cell parameters from 4890 reflections
b = 11.1880 (5) Å	θ = 4.0–75.8°
c = 11.7618 (6) Å	µ = 8.59 mm^−1
α = 73.609 (4)°	T = 293 K
β = 76.945 (4)°	Prism, pale yellow
γ = 79.342 (4)°	0.15 × 0.15 × 0.10 mm
V = 960.15 (7) Å^3

Data collection

Oxford Diffraction Xcalibur Nova R diffractometer	3932 independent reflections
Graphite monochromator	3371 reflections with I > 2σ(I)
Detector resolution: 10.4323 pixels mm^-1	Rint = 0.033
ω scans	θmax = 76.0°, θmin = 4.0°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	h = −9→9
Tmin = 0.518, Tmax = 1	k = −13→13
8031 measured reflections	l = −14→11

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.085P)^2 + 0.0501P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.129	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.47 e Å^−3
3932 reflections	Δρmin = −0.33 e Å^−3
250 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
V2	0.96401 (5)	0.16480 (4)	0.30891 (4)	0.04115 (14)
V1	0.95947 (5)	−0.13283 (4)	0.42124 (4)	0.03986 (14)
O1	0.9714 (3)	−0.24965 (19)	0.3592 (2)	0.0530 (5)
O2	1.0932 (2)	−0.17853 (19)	0.53675 (18)	0.0498 (4)
O3	0.7553 (3)	−0.0950 (2)	0.4789 (2)	0.0589 (5)
O4	1.0430 (2)	0.00128 (17)	0.30665 (17)	0.0473 (4)
O5	0.7916 (3)	0.2148 (2)	0.2444 (2)	0.0575 (5)
O6	1.1255 (3)	0.2451 (2)	0.2325 (2)	0.0600 (5)
C1	0.5148 (3)	0.6860 (2)	0.4084 (2)	0.0446 (5)
C2	0.3830 (4)	0.6228 (3)	0.3964 (3)	0.0489 (6)
H2	0.2663	0.645	0.4292	0.059*
C3	0.4245 (5)	0.5298 (3)	0.3373 (3)	0.0577 (7)
C4	0.6019 (5)	0.4953 (3)	0.2905 (3)	0.0647 (8)
H4	0.6333	0.4311	0.2509	0.078*
C5	0.7261 (4)	0.5561 (3)	0.3034 (3)	0.0620 (7)
H5	0.8432	0.534	0.2714	0.074*
C6	0.2802 (6)	0.4652 (4)	0.3238 (4)	0.0836 (12)
H6C	0.3308	0.4022	0.2805	0.125*
H6A	0.1994	0.526	0.2801	0.125*
H6B	0.2188	0.4264	0.4021	0.125*
N1	0.6839 (3)	0.6492 (2)	0.3625 (2)	0.0497 (5)
H1	0.7662	0.6853	0.3708	0.06*
N2	0.4799 (3)	0.7794 (2)	0.4625 (2)	0.0547 (6)
H2A	0.5642	0.8155	0.4679	0.066*
H2B	0.3731	0.8038	0.4921	0.066*
C7	0.5200 (4)	1.0124 (3)	0.2050 (3)	0.0523 (6)
C8	0.6928 (4)	0.9673 (3)	0.1585 (3)	0.0521 (6)
H8	0.7863	1.0016	0.1677	0.062*
C9	0.7251 (4)	0.8738 (3)	0.1000 (3)	0.0563 (7)
C10	0.5819 (5)	0.8220 (3)	0.0874 (3)	0.0622 (7)
H10	0.6011	0.7592	0.0466	0.075*
C11	0.4163 (4)	0.8645 (3)	0.1352 (3)	0.0601 (7)
H11	0.3217	0.8295	0.1287	0.072*
C12	0.9095 (5)	0.8251 (4)	0.0517 (4)	0.0783 (10)
H12B	0.9078	0.7602	0.0133	0.117*
H12A	0.9734	0.7914	0.1167	0.117*
H12C	0.9656	0.8924	−0.0061	0.117*
N3	0.3879 (3)	0.9573 (3)	0.1922 (2)	0.0559 (6)
H3	0.2815	0.9827	0.2218	0.067*
N4	0.4820 (4)	1.1037 (3)	0.2601 (3)	0.0750 (8)
H4A	0.3743	1.1281	0.2878	0.09*
H4B	0.5649	1.1391	0.2686	0.09*
O9	0.3335 (12)	0.6497 (8)	−0.0146 (6)	0.186 (3)
O7	0.0661 (13)	0.4852 (7)	0.0806 (8)	0.121 (3)	0.5
O8	0.754 (2)	0.5676 (10)	−0.0400 (7)	0.191 (7)	0.5
H9A	0.255 (15)	0.616 (10)	−0.047 (11)	0.3*
H9B	0.385 (17)	0.573 (7)	0.037 (10)	0.3*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
V2	0.0395 (2)	0.0430 (2)	0.0433 (2)	−0.00904 (16)	−0.01011 (16)	−0.01024 (17)
V1	0.0361 (2)	0.0433 (2)	0.0449 (2)	−0.00975 (15)	−0.00796 (16)	−0.01537 (17)
O1	0.0542 (10)	0.0535 (10)	0.0622 (12)	−0.0098 (8)	−0.0159 (9)	−0.0259 (9)
O2	0.0471 (9)	0.0566 (10)	0.0500 (10)	−0.0079 (8)	−0.0129 (8)	−0.0164 (8)
O3	0.0415 (9)	0.0704 (13)	0.0701 (13)	−0.0124 (8)	−0.0044 (9)	−0.0273 (11)
O4	0.0453 (9)	0.0458 (9)	0.0518 (10)	−0.0089 (7)	−0.0060 (7)	−0.0141 (8)
O5	0.0538 (11)	0.0611 (12)	0.0635 (12)	−0.0017 (9)	−0.0250 (9)	−0.0175 (10)
O6	0.0578 (11)	0.0601 (12)	0.0615 (12)	−0.0238 (9)	−0.0071 (9)	−0.0069 (10)
C1	0.0447 (12)	0.0455 (12)	0.0445 (12)	−0.0119 (9)	−0.0129 (10)	−0.0050 (10)
C2	0.0446 (12)	0.0478 (13)	0.0556 (15)	−0.0120 (10)	−0.0164 (11)	−0.0057 (11)
C3	0.0701 (17)	0.0508 (14)	0.0603 (17)	−0.0165 (13)	−0.0298 (14)	−0.0074 (13)
C4	0.082 (2)	0.0559 (16)	0.0640 (18)	−0.0073 (15)	−0.0203 (16)	−0.0231 (14)
C5	0.0563 (16)	0.0669 (18)	0.0613 (18)	−0.0024 (13)	−0.0081 (13)	−0.0192 (15)
C6	0.103 (3)	0.071 (2)	0.098 (3)	−0.033 (2)	−0.049 (2)	−0.018 (2)
N1	0.0434 (11)	0.0548 (12)	0.0530 (13)	−0.0138 (9)	−0.0096 (9)	−0.0113 (10)
N2	0.0443 (11)	0.0592 (13)	0.0667 (15)	−0.0142 (9)	−0.0080 (10)	−0.0224 (12)
C7	0.0422 (13)	0.0661 (16)	0.0475 (14)	−0.0106 (11)	−0.0094 (10)	−0.0095 (12)
C8	0.0453 (13)	0.0668 (17)	0.0436 (13)	−0.0120 (11)	−0.0086 (10)	−0.0097 (12)
C9	0.0547 (15)	0.0694 (18)	0.0410 (13)	−0.0093 (13)	−0.0070 (11)	−0.0086 (12)
C10	0.0710 (19)	0.0665 (18)	0.0530 (16)	−0.0120 (15)	−0.0173 (14)	−0.0147 (14)
C11	0.0597 (16)	0.0683 (18)	0.0555 (16)	−0.0216 (14)	−0.0220 (13)	−0.0033 (14)
C12	0.066 (2)	0.097 (3)	0.069 (2)	−0.0061 (18)	0.0031 (17)	−0.032 (2)
N3	0.0404 (11)	0.0698 (15)	0.0544 (13)	−0.0123 (10)	−0.0082 (9)	−0.0077 (11)
N4	0.0472 (13)	0.090 (2)	0.097 (2)	−0.0088 (13)	−0.0057 (14)	−0.0436 (19)
O9	0.225 (8)	0.230 (8)	0.116 (4)	−0.091 (6)	−0.042 (4)	−0.016 (5)
O7	0.161 (8)	0.072 (4)	0.101 (6)	−0.012 (4)	−0.004 (5)	0.007 (4)
O8	0.38 (2)	0.118 (7)	0.071 (5)	−0.122 (11)	0.017 (8)	−0.006 (5)

Geometric parameters (Å, º)

V2—O5	1.636 (2)	N2—H2A	0.86
V2—O6	1.637 (2)	N2—H2B	0.86
V2—O2^i	1.812 (2)	C7—N4	1.314 (4)
V2—O4	1.8258 (18)	C7—N3	1.358 (4)
V1—O3	1.625 (2)	C7—C8	1.404 (4)
V1—O1	1.6467 (19)	C8—C9	1.364 (5)
V1—O2	1.809 (2)	C8—H8	0.93
V1—O4	1.8232 (19)	C9—C10	1.414 (5)
O2—V2^i	1.812 (2)	C9—C12	1.495 (5)
C1—N2	1.328 (4)	C10—C11	1.353 (5)
C1—N1	1.353 (4)	C10—H10	0.93
C1—C2	1.411 (4)	C11—N3	1.349 (5)
C2—C3	1.361 (4)	C11—H11	0.93
C2—H2	0.93	C12—H12B	0.96
C3—C4	1.406 (5)	C12—H12A	0.96
C3—C6	1.513 (4)	C12—H12C	0.96
C4—C5	1.346 (5)	N3—H3	0.86
C4—H4	0.93	N4—H4A	0.86
C5—N1	1.362 (4)	N4—H4B	0.86
C5—H5	0.93	O9—H9A	0.97 (2)
C6—H6C	0.96	O9—H9B	0.98 (2)
C6—H6A	0.96	O7—O8^ii	1.460 (18)
C6—H6B	0.96	O8—O7^ii	1.460 (18)
N1—H1	0.86
O5—V2—O6	109.93 (12)	C1—N1—C5	121.2 (3)
O5—V2—O2^i	109.51 (10)	C1—N1—H1	119.4
O6—V2—O2^i	111.16 (11)	C5—N1—H1	119.4
O5—V2—O4	110.27 (10)	C1—N2—H2A	120
O6—V2—O4	106.15 (10)	C1—N2—H2B	120
O2^i—V2—O4	109.79 (9)	H2A—N2—H2B	120
O3—V1—O1	108.79 (11)	N4—C7—N3	119.4 (3)
O3—V1—O2	110.32 (11)	N4—C7—C8	123.0 (3)
O1—V1—O2	110.20 (10)	N3—C7—C8	117.5 (3)
O3—V1—O4	110.02 (11)	C9—C8—C7	120.8 (3)
O1—V1—O4	109.41 (10)	C9—C8—H8	119.6
O2—V1—O4	108.10 (9)	C7—C8—H8	119.6
V1—O2—V2^i	129.30 (11)	C8—C9—C10	119.0 (3)
V1—O4—V2	123.94 (10)	C8—C9—C12	120.7 (3)
N2—C1—N1	118.9 (2)	C10—C9—C12	120.3 (3)
N2—C1—C2	122.9 (3)	C11—C10—C9	119.4 (3)
N1—C1—C2	118.2 (3)	C11—C10—H10	120.3
C3—C2—C1	120.8 (3)	C9—C10—H10	120.3
C3—C2—H2	119.6	N3—C11—C10	120.4 (3)
C1—C2—H2	119.6	N3—C11—H11	119.8
C2—C3—C4	118.9 (3)	C10—C11—H11	119.8
C2—C3—C6	119.7 (3)	C9—C12—H12B	109.5
C4—C3—C6	121.4 (3)	C9—C12—H12A	109.5
C5—C4—C3	119.5 (3)	H12B—C12—H12A	109.5
C5—C4—H4	120.3	C9—C12—H12C	109.5
C3—C4—H4	120.3	H12B—C12—H12C	109.5
C4—C5—N1	121.4 (3)	H12A—C12—H12C	109.5
C4—C5—H5	119.3	C11—N3—C7	122.8 (3)
N1—C5—H5	119.3	C11—N3—H3	118.6
C3—C6—H6C	109.5	C7—N3—H3	118.6
C3—C6—H6A	109.5	C7—N4—H4A	120
H6C—C6—H6A	109.5	C7—N4—H4B	120
C3—C6—H6B	109.5	H4A—N4—H4B	120
H6C—C6—H6B	109.5	H9A—O9—H9B	102 (4)
H6A—C6—H6B	109.5
O3—V1—O2—V2^i	−9.82 (19)	C3—C4—C5—N1	0.9 (5)
O1—V1—O2—V2^i	−129.97 (15)	N2—C1—N1—C5	−178.3 (3)
O4—V1—O2—V2^i	110.52 (14)	C2—C1—N1—C5	1.7 (4)
O3—V1—O4—V2	29.34 (16)	C4—C5—N1—C1	−1.3 (5)
O1—V1—O4—V2	148.80 (13)	N4—C7—C8—C9	−178.8 (3)
O2—V1—O4—V2	−91.18 (13)	N3—C7—C8—C9	1.7 (5)
O5—V2—O4—V1	−86.26 (15)	C7—C8—C9—C10	−0.5 (5)
O6—V2—O4—V1	154.71 (13)	C7—C8—C9—C12	−179.4 (3)
O2^i—V2—O4—V1	34.48 (15)	C8—C9—C10—C11	−1.1 (5)
N2—C1—C2—C3	178.2 (3)	C12—C9—C10—C11	177.8 (3)
N1—C1—C2—C3	−1.8 (4)	C9—C10—C11—N3	1.4 (5)
C1—C2—C3—C4	1.4 (5)	C10—C11—N3—C7	0.0 (5)
C1—C2—C3—C6	−178.9 (3)	N4—C7—N3—C11	179.0 (3)
C2—C3—C4—C5	−1.0 (5)	C8—C7—N3—C11	−1.5 (4)
C6—C3—C4—C5	179.3 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^iii	0.86	1.85	2.700 (3)	167
N2—H2A···O3^iii	0.86	2.00	2.861 (3)	178
N2—H2B···O2^iv	0.86	2.13	2.959 (3)	161
N3—H3···O4^iv	0.86	1.92	2.767 (3)	167
N4—H4A···O6^iv	0.86	2.26	2.995 (4)	143
N4—H4B···O5^iii	0.86	2.04	2.883 (4)	165
C2—H2···O1^iv	0.93	2.60	3.363 (4)	140
C2—H2···O2^iv	0.93	2.64	3.371 (4)	136
C4—H4···O5	0.93	2.52	3.352 (4)	149

Symmetry codes: (iii) x, y+1, z; (iv) x−1, y+1, z.