1,3,5-Tri­aza-7-phosphaadamantan-1-ium nitrate

Adeleke, A.A.; Zamisa, S.J.; Omondi, B.; Olatunji, O.S.

doi:10.1107/S2414314626009296

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 9| September 2026| x260929

https://doi.org/10.1107/S2414314626009296

Open

access

1,3,5-Triaza-7-phosphaadamantan-1-ium nitrate

Adesola A. Adeleke,^a,^b ^* Sizwe J. Zamisa,^a Bernard Omondi ^a and Olatunde S. Olatunji ^a

^aSchool of Agriculture and Science, Discipline of Chemistry, University of KwaZulu-Natal, Private Bag X54001, Durban, 4000, South Africa, and ^bDepartment of Chemical Sciences, Olabisi Onabanjo University, Ago-Iwoye, Nigeria
^*Correspondence e-mail: [email protected]

Edited by R. J. Butcher, Howard University, USA (Received 13 August 2026; accepted 4 September 2026; online 11 September 2026)

The title salt, C₆H₁₃N₃P⁺·NO₃⁻ or [PTAH][NO₃], crystallizes in the triclinic space group P1 with two independent PTAH⁺ cations and two nitrate anions in the asymmetric unit. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link the PTAH⁺ and oxygen atoms of the nitrate anion, forming a three-dimensional supramolecular structure.

Keywords: crystal structure; PTAH⁺; nitrate salt; supramolecular network.

CCDC reference: 2585607

Structure description

1,3,5-Triaza-7-phosphaadamantane (PTA) is a well established water-soluble cage-type phosphine that incorporates a soft phosphorus donor atom at the bridgehead position 7 and three nitrogen atoms at positions 1, 3, and 5 of an adamantane-like bicyclic framework (Daigle et al., 1998 ). Protonation at one of these nitrogen atoms readily yields the PTAH⁺ (C₆H₁₃N₃P⁺) cation, which is commonly encountered during the synthesis of PTA-based metal–phosphine complexes (Kirillov et al., 2007 ; Tu et al., 2008 ).

The title compound shows solid-state structural features for a N– protonated PTAH⁺ cage in the absence of metal coordination. The asymmetric unit of the title compound contains two independent PTAH⁺ cations together with two nitrate anions (Fig. 1). The P—C bond distances in the PTA moieties are between 1.847 (4) and 1.856 (3) Å with C—P—C bond angles between 96.7 (1) and 96.8 (2)°. The N—C bond distances of the non-protonated nitrogen atoms of both PTA moieties are between 1.434 (5)–1.482 (5) Å, while the N—C distances at the protonation nitrogen centres are observed between 1.501 (4) and 1.524 (5) Å. The N—C distances at the protonated N atoms are notably longer than N—C distances of the non-protonated nitrogen atoms of the PTA moieties, which are consistent with the expected weakening of N—C bonds upon quaternization of the nitrogen atom. All distances and angles are in good agreement with those reported for structurally related PTA-based compounds (Akbayeva et al., 2005 ; Kirillov et al., 2007; Tu et al., 2008 ). In the crystal, N—H⋯O, N—H⋯(O,O) and C—H⋯O hydrogen bonds (Table 1) link the PTAH⁺ NH groupings and oxygen atoms of the nitrate anion, forming a three-dimensional supramolecular structure as depicted in Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.88 (3)	1.89 (3)	2.7576 (18)	166
N4—H4⋯O2ⁱⁱ	0.90 (3)	2.09 (3)	2.9076 (19)	151
N4—H4⋯O3ⁱⁱ	0.90 (3)	2.16 (3)	2.9448 (19)	145
C2—H2B⋯O4	0.99	2.30	3.202 (2)	151
Symmetry codes: (i) ; (ii) .

Figure 1
The molecular structure of (I) shown with displacement ellipsoids at the 50% probability level. All C-bound hydrogen atoms are omitted for clarity.

Figure 2
Representation of N—H⋯O and C—H⋯O hydrogen bonds in the crystal structure of (I) (cyan dotted bonds).

Synthesis and crystallization

PTA was prepared according to the literature method (Daigle et al., 1998). In an attempt to synthesize a PTA–Zn^II complex, an aqueous solution of Zn(NO₃)₂·6H₂O (0.297 g, 1.0 mmol) in distilled water (5 ml) was added to a solution of PTA (0.312 g, 2.0 mmol) in distilled water (10 ml) and the mixture was stirred at room temperature for 30 minutes. The colourless solution was filtered and the filtrate was transferred to an open vial and allowed to evaporate slowly at ambient temperature. After several days, colourless block-shaped crystals of the title compound, [PTAH]₂[NO₃]₂, were isolated and identified by single-crystal X-ray diffraction analysis. The formation of the protonated phosphine salt rather than the intended Zn^II complex can be attributed to N-protonation of PTA in the weakly acidic nitrate medium, which is consistent with a related literature report (Akbayeva et al., 2005).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The crystal chosen for data collection was found to be twinned and was modelled using twin law (1 0 0) with a BASF value of 0.0628 (6).

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₁₃N₃P⁺·NO₃⁻
M_r	220.17
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	7.0750 (3), 9.8950 (4), 13.6434 (5)
α, β, γ (°)	102.614 (2), 90.123 (2), 90.613 (2)
V (Å³)	932.02 (6)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.29
Crystal size (mm)	0.34 × 0.31 × 0.23

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.892, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	14497, 4661, 4486
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.100, 1.12
No. of reflections	4661
No. of parameters	262
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.42
Computer programs: APEX2, SAINT, SAINT-Plus and XPREP (Bruker, 2008 ), OLEX2.solve (Bourhis et al., 2015 ), SHELXL2018/3 (Sheldrick, 2015) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2585607

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626009296/bv4062sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626009296/bv4062Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626009296/bv4062Isup3.cml

checkCIF report

Computing details top

1,3,5-Triaza-7-phosphaadamantan-1-ium nitrate top

Crystal data top

C₆H₁₃N₃P⁺·NO₃⁻	Z = 4
M_r = 220.17	F(000) = 464
Triclinic, P1	D_x = 1.569 Mg m⁻³
a = 7.0750 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8950 (4) Å	Cell parameters from 9920 reflections
c = 13.6434 (5) Å	θ = 2.9–28.7°
α = 102.614 (2)°	µ = 0.28 mm⁻¹
β = 90.123 (2)°	T = 100 K
γ = 90.613 (2)°	Block, colourless
V = 932.02 (6) Å³	0.34 × 0.31 × 0.23 mm

Data collection top

Bruker APEXII CCD diffractometer	4661 independent reflections
Graphite monochromator	4486 reflections with I > 2σ(I)
Detector resolution: 8 pixels mm^-1	R_int = 0.024
φ and ω scans	θ_max = 28.7°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→9
T_min = 0.892, T_max = 0.937	k = −13→11
14497 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0489P)² + 0.5707P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max = 0.001
4661 reflections	Δρ_max = 0.58 e Å⁻³
262 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints

Special details top

Experimental. School of Agriculture and Science, Discipline of Chemistry, University of KwaZulu-Natal, Private Bag X54001, Durban, 4000, South Africa

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5452 (2)	0.58160 (17)	0.67349 (12)	0.0177 (3)
H1A	0.559898	0.484998	0.635389	0.021*
H1B	0.430137	0.584724	0.715039	0.021*
C2	0.9257 (2)	0.64444 (17)	0.65902 (11)	0.0159 (3)
H2A	1.043130	0.688530	0.691149	0.019*
H2B	0.957663	0.550475	0.620874	0.019*
C3	0.7049 (2)	0.81794 (16)	0.79430 (11)	0.0151 (3)
H3A	0.598675	0.832972	0.842440	0.018*
H3B	0.817625	0.865805	0.829325	0.018*
C4	0.6744 (2)	0.66343 (17)	0.53348 (11)	0.0171 (3)
H4A	0.642100	0.712138	0.479655	0.020*
H4B	0.697789	0.565164	0.501755	0.020*
C5	0.8137 (2)	0.87607 (16)	0.64080 (11)	0.0159 (3)
H5A	0.928007	0.916872	0.678346	0.019*
H5B	0.783790	0.931556	0.590665	0.019*
C6	0.4904 (2)	0.81704 (18)	0.65371 (12)	0.0186 (3)
H6A	0.455189	0.871198	0.603550	0.022*
H6B	0.383885	0.821402	0.701167	0.022*
C7	0.3115 (3)	0.09677 (17)	0.85258 (12)	0.0202 (3)
H7A	0.422824	0.046099	0.820145	0.024*
H7B	0.267050	0.050265	0.905718	0.024*
C8	−0.0136 (2)	0.14861 (17)	0.82629 (13)	0.0208 (3)
H8A	−0.051385	0.095291	0.876739	0.025*
H8B	−0.113529	0.134999	0.774059	0.025*
C9	0.2147 (3)	0.32251 (19)	0.96221 (12)	0.0209 (3)
H9A	0.260870	0.416957	0.993355	0.025*
H9B	0.182965	0.275116	1.016978	0.025*
C10	0.2283 (2)	0.16418 (17)	0.70205 (11)	0.0166 (3)
H10A	0.126133	0.160151	0.651774	0.020*
H10B	0.338778	0.115395	0.667117	0.020*
C11	0.1177 (2)	0.39337 (17)	0.78380 (12)	0.0186 (3)
H11A	0.024661	0.390929	0.729145	0.022*
H11B	0.159792	0.490778	0.807723	0.022*
C12	0.4297 (2)	0.31706 (18)	0.81655 (12)	0.0187 (3)
H12A	0.461679	0.415170	0.846099	0.022*
H12B	0.544255	0.272155	0.783434	0.022*
N5	0.1644 (2)	0.09148 (14)	0.77929 (10)	0.0167 (3)
N4	0.3693 (2)	0.24516 (15)	0.89982 (10)	0.0181 (3)
N6	0.2811 (2)	0.31048 (14)	0.74263 (9)	0.0161 (3)
N2	0.51768 (19)	0.67146 (15)	0.60160 (10)	0.0169 (3)
N1	0.85319 (19)	0.72773 (14)	0.58714 (10)	0.0144 (2)
N3	0.65804 (19)	0.88163 (14)	0.70931 (10)	0.0148 (3)
N7	0.2859 (2)	0.76573 (15)	0.93218 (10)	0.0174 (3)
N8	0.78748 (19)	0.20712 (15)	0.55432 (10)	0.0164 (3)
O1	0.1566 (2)	0.77076 (17)	0.87169 (11)	0.0342 (3)
O2	0.31980 (19)	0.86667 (14)	1.00409 (9)	0.0235 (3)
O3	0.38752 (19)	0.65990 (14)	0.92249 (10)	0.0240 (3)
O4	0.87968 (18)	0.32028 (13)	0.56299 (9)	0.0223 (3)
O5	0.83586 (18)	0.10535 (13)	0.48843 (9)	0.0217 (3)
O6	0.6530 (2)	0.19967 (16)	0.61060 (11)	0.0323 (3)
P1	0.75278 (6)	0.62929 (4)	0.75817 (3)	0.01556 (10)
P2	−0.00150 (6)	0.33549 (4)	0.88862 (3)	0.01797 (10)
H1	0.941 (4)	0.728 (3)	0.5413 (18)	0.029 (6)*
H4	0.471 (4)	0.243 (3)	0.9390 (19)	0.034 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0194 (7)	0.0160 (7)	0.0186 (7)	−0.0037 (6)	−0.0006 (6)	0.0059 (6)
C2	0.0172 (7)	0.0147 (7)	0.0165 (7)	0.0023 (5)	−0.0009 (5)	0.0051 (5)
C3	0.0196 (7)	0.0144 (7)	0.0115 (6)	0.0003 (5)	0.0004 (5)	0.0032 (5)
C4	0.0208 (7)	0.0183 (8)	0.0120 (6)	−0.0022 (6)	−0.0039 (5)	0.0033 (5)
C5	0.0219 (7)	0.0111 (7)	0.0154 (6)	−0.0009 (5)	0.0022 (6)	0.0040 (5)
C6	0.0169 (7)	0.0191 (8)	0.0200 (7)	0.0036 (6)	−0.0029 (6)	0.0048 (6)
C7	0.0282 (8)	0.0148 (7)	0.0193 (7)	0.0062 (6)	0.0012 (6)	0.0072 (6)
C8	0.0197 (7)	0.0151 (7)	0.0257 (8)	−0.0020 (6)	0.0059 (6)	0.0002 (6)
C9	0.0258 (8)	0.0244 (8)	0.0118 (6)	0.0045 (7)	0.0010 (6)	0.0019 (6)
C10	0.0218 (7)	0.0163 (7)	0.0114 (6)	0.0026 (6)	0.0008 (5)	0.0023 (5)
C11	0.0215 (7)	0.0160 (7)	0.0193 (7)	0.0044 (6)	−0.0001 (6)	0.0057 (6)
C12	0.0167 (7)	0.0207 (8)	0.0194 (7)	−0.0014 (6)	0.0004 (6)	0.0060 (6)
N5	0.0193 (6)	0.0136 (6)	0.0174 (6)	0.0012 (5)	0.0029 (5)	0.0036 (5)
N4	0.0202 (7)	0.0209 (7)	0.0135 (6)	0.0041 (5)	−0.0034 (5)	0.0045 (5)
N6	0.0204 (6)	0.0162 (6)	0.0121 (5)	−0.0024 (5)	0.0010 (5)	0.0043 (5)
N2	0.0169 (6)	0.0179 (7)	0.0159 (6)	0.0002 (5)	−0.0032 (5)	0.0037 (5)
N1	0.0178 (6)	0.0137 (6)	0.0120 (5)	−0.0006 (5)	0.0017 (5)	0.0033 (5)
N3	0.0173 (6)	0.0133 (6)	0.0146 (6)	0.0019 (5)	0.0006 (5)	0.0049 (5)
N7	0.0176 (6)	0.0206 (7)	0.0158 (6)	−0.0032 (5)	−0.0009 (5)	0.0079 (5)
N8	0.0166 (6)	0.0200 (7)	0.0139 (6)	0.0022 (5)	−0.0001 (5)	0.0067 (5)
O1	0.0320 (7)	0.0357 (8)	0.0363 (8)	−0.0024 (6)	−0.0197 (6)	0.0108 (6)
O2	0.0307 (7)	0.0216 (6)	0.0174 (5)	−0.0017 (5)	−0.0020 (5)	0.0028 (5)
O3	0.0247 (6)	0.0220 (6)	0.0256 (6)	0.0031 (5)	0.0005 (5)	0.0057 (5)
O4	0.0259 (6)	0.0189 (6)	0.0207 (6)	−0.0038 (5)	0.0005 (5)	0.0014 (5)
O5	0.0263 (6)	0.0163 (6)	0.0219 (6)	0.0030 (5)	0.0035 (5)	0.0029 (5)
O6	0.0290 (7)	0.0378 (8)	0.0317 (7)	0.0015 (6)	0.0165 (6)	0.0113 (6)
P1	0.0199 (2)	0.01446 (19)	0.01372 (17)	0.00056 (15)	−0.00136 (14)	0.00611 (14)
P2	0.0180 (2)	0.0162 (2)	0.01841 (19)	0.00172 (15)	0.00339 (15)	0.00101 (15)

Geometric parameters (Å, º) top

C1—H1A	0.9900	C8—H8A	0.9900
C1—H1B	0.9900	C8—H8B	0.9900
C1—N2	1.475 (2)	C8—N5	1.475 (2)
C1—P1	1.8583 (17)	C8—P2	1.8599 (17)
C2—H2A	0.9900	C9—H9A	0.9900
C2—H2B	0.9900	C9—H9B	0.9900
C2—N1	1.5046 (19)	C9—N4	1.498 (2)
C2—P1	1.8550 (16)	C9—P2	1.8488 (18)
C3—H3A	0.9900	C10—H10A	0.9900
C3—H3B	0.9900	C10—H10B	0.9900
C3—N3	1.4744 (19)	C10—N5	1.469 (2)
C3—P1	1.8587 (16)	C10—N6	1.476 (2)
C4—H4A	0.9900	C11—H11A	0.9900
C4—H4B	0.9900	C11—H11B	0.9900
C4—N2	1.440 (2)	C11—N6	1.465 (2)
C4—N1	1.522 (2)	C11—P2	1.8539 (17)
C5—H5A	0.9900	C12—H12A	0.9900
C5—H5B	0.9900	C12—H12B	0.9900
C5—N1	1.519 (2)	C12—N4	1.526 (2)
C5—N3	1.440 (2)	C12—N6	1.447 (2)
C6—H6A	0.9900	N4—H4	0.90 (3)
C6—H6B	0.9900	N1—H1	0.88 (3)
C6—N2	1.475 (2)	N7—O1	1.2395 (19)
C6—N3	1.469 (2)	N7—O2	1.2583 (19)
C7—H7A	0.9900	N7—O3	1.2598 (19)
C7—H7B	0.9900	N8—O4	1.2726 (19)
C7—N5	1.434 (2)	N8—O5	1.2461 (18)
C7—N4	1.520 (2)	N8—O6	1.2358 (18)

H1A—C1—H1B	107.6	H10A—C10—H10B	107.7
N2—C1—H1A	108.7	N5—C10—H10A	108.9
N2—C1—H1B	108.7	N5—C10—H10B	108.9
N2—C1—P1	114.41 (11)	N5—C10—N6	113.46 (12)
P1—C1—H1A	108.7	N6—C10—H10A	108.9
P1—C1—H1B	108.7	N6—C10—H10B	108.9
H2A—C2—H2B	107.8	H11A—C11—H11B	107.6
N1—C2—H2A	109.0	N6—C11—H11A	108.6
N1—C2—H2B	109.0	N6—C11—H11B	108.6
N1—C2—P1	112.97 (10)	N6—C11—P2	114.53 (11)
P1—C2—H2A	109.0	P2—C11—H11A	108.6
P1—C2—H2B	109.0	P2—C11—H11B	108.6
H3A—C3—H3B	107.6	H12A—C12—H12B	108.0
N3—C3—H3A	108.7	N4—C12—H12A	109.4
N3—C3—H3B	108.7	N4—C12—H12B	109.4
N3—C3—P1	114.36 (10)	N6—C12—H12A	109.4
P1—C3—H3A	108.7	N6—C12—H12B	109.4
P1—C3—H3B	108.7	N6—C12—N4	111.18 (13)
H4A—C4—H4B	108.0	C7—N5—C8	111.48 (13)
N2—C4—H4A	109.3	C7—N5—C10	109.32 (13)
N2—C4—H4B	109.3	C10—N5—C8	111.82 (13)
N2—C4—N1	111.63 (12)	C7—N4—C12	108.65 (12)
N1—C4—H4A	109.3	C7—N4—H4	108.4 (17)
N1—C4—H4B	109.3	C9—N4—C7	112.16 (14)
H5A—C5—H5B	108.0	C9—N4—C12	111.31 (13)
N1—C5—H5A	109.4	C9—N4—H4	108.9 (17)
N1—C5—H5B	109.4	C12—N4—H4	107.3 (17)
N3—C5—H5A	109.4	C11—N6—C10	111.89 (13)
N3—C5—H5B	109.4	C12—N6—C10	109.13 (13)
N3—C5—N1	111.00 (12)	C12—N6—C11	111.92 (12)
H6A—C6—H6B	107.7	C1—N2—C6	111.46 (12)
N2—C6—H6A	108.8	C4—N2—C1	111.54 (13)
N2—C6—H6B	108.8	C4—N2—C6	109.34 (13)
N3—C6—H6A	108.8	C2—N1—C4	111.58 (12)
N3—C6—H6B	108.8	C2—N1—C5	111.25 (12)
N3—C6—N2	113.82 (13)	C2—N1—H1	107.7 (16)
H7A—C7—H7B	108.0	C4—N1—H1	107.9 (16)
N5—C7—H7A	109.3	C5—N1—C4	109.21 (12)
N5—C7—H7B	109.3	C5—N1—H1	109.1 (17)
N5—C7—N4	111.52 (13)	C5—N3—C3	111.94 (12)
N4—C7—H7A	109.3	C5—N3—C6	109.19 (12)
N4—C7—H7B	109.3	C6—N3—C3	112.10 (13)
H8A—C8—H8B	107.6	O1—N7—O2	120.77 (15)
N5—C8—H8A	108.6	O1—N7—O3	120.72 (15)
N5—C8—H8B	108.6	O2—N7—O3	118.50 (14)
N5—C8—P2	114.68 (11)	O5—N8—O4	118.67 (13)
P2—C8—H8A	108.6	O6—N8—O4	120.04 (15)
P2—C8—H8B	108.6	O6—N8—O5	121.29 (15)
H9A—C9—H9B	107.8	C1—P1—C3	96.70 (7)
N4—C9—H9A	109.0	C2—P1—C1	96.64 (7)
N4—C9—H9B	109.0	C2—P1—C3	94.86 (7)
N4—C9—P2	112.85 (10)	C9—P2—C8	95.54 (8)
P2—C9—H9A	109.0	C9—P2—C11	96.54 (8)
P2—C9—H9B	109.0	C11—P2—C8	96.12 (8)

N5—C7—N4—C9	66.80 (17)	N1—C2—P1—C1	47.23 (12)
N5—C7—N4—C12	−56.67 (17)	N1—C2—P1—C3	−50.11 (12)
N5—C8—P2—C9	−50.15 (14)	N1—C4—N2—C1	−68.34 (17)
N5—C8—P2—C11	47.06 (14)	N1—C4—N2—C6	55.40 (16)
N5—C10—N6—C11	−66.12 (17)	N1—C5—N3—C3	67.37 (16)
N5—C10—N6—C12	58.29 (17)	N1—C5—N3—C6	−57.35 (16)
N4—C7—N5—C8	−66.85 (17)	N3—C3—P1—C1	−46.57 (12)
N4—C7—N5—C10	57.29 (16)	N3—C3—P1—C2	50.72 (12)
N4—C9—P2—C8	48.69 (14)	N3—C5—N1—C2	−67.05 (16)
N4—C9—P2—C11	−48.14 (14)	N3—C5—N1—C4	56.55 (16)
N4—C12—N6—C10	−56.64 (16)	N3—C6—N2—C1	66.20 (17)
N4—C12—N6—C11	67.76 (17)	N3—C6—N2—C4	−57.59 (17)
N6—C10—N5—C7	−58.57 (17)	P1—C1—N2—C4	62.84 (15)
N6—C10—N5—C8	65.37 (17)	P1—C1—N2—C6	−59.69 (15)
N6—C11—P2—C8	−47.61 (13)	P1—C2—N1—C4	−59.88 (14)
N6—C11—P2—C9	48.71 (13)	P1—C2—N1—C5	62.35 (15)
N6—C12—N4—C7	56.30 (17)	P1—C3—N3—C5	−64.15 (15)
N6—C12—N4—C9	−67.68 (17)	P1—C3—N3—C6	58.94 (15)
N2—C1—P1—C2	−48.54 (13)	P2—C8—N5—C7	63.47 (17)
N2—C1—P1—C3	47.17 (12)	P2—C8—N5—C10	−59.25 (16)
N2—C4—N1—C2	67.66 (16)	P2—C9—N4—C7	−60.94 (16)
N2—C4—N1—C5	−55.74 (16)	P2—C9—N4—C12	61.03 (16)
N2—C6—N3—C3	−65.97 (17)	P2—C11—N6—C10	60.33 (15)
N2—C6—N3—C5	58.66 (17)	P2—C11—N6—C12	−62.51 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.88 (3)	1.89 (3)	2.7576 (18)	166
N4—H4···O2ⁱⁱ	0.90 (3)	2.09 (3)	2.9076 (19)	151
N4—H4···O3ⁱⁱ	0.90 (3)	2.16 (3)	2.9448 (19)	145
C2—H2B···O4	0.99	2.30	3.202 (2)	151

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

Acknowledgements

We thank the University of KwaZulu-Natal for their support of this research.

References

Akbayeva, D. N., Moneti, S., Peruzzini, M., Gonsalvi, L., Ienco, A. & Vizza, F. (2005). C. R. Chim. 8, 1491–1496. CrossRef CAS Google Scholar
Bourhis, L. J., Dolomanov, O. V., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2015). Acta Cryst. A71, 59–75. Web of Science CrossRef IUCr Journals Google Scholar
Bruker (2014). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Daigle, D. J., Poulain, N., Harvey, P. D. & Bhatt, S. (1998). Inorg. Synth. 32, 40–45. CrossRef CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Kirillov, A. M., Smoleński, P., Guedes da Silva, M. F. C. & Pombeiro, A. J. (2007). Eur. J. Inorg. Chem. pp. 2686–2692. CrossRef Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Tu, X., Nichol, G. S., Wang, R. & Zheng, Z. (2008). Dalton Trans. pp. 6030–6038. CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.