Tris(ethyl-enediamine-κ(2)N,N')nickel(II) bis-(dimethyl phosphate).

In the title compound, [Ni(C(2)H(8)N(2))(3)][O(2)P(OCH(3))(2)](2), the Ni(II) atom is six-coordinated in a distorted octa-hedral geometry by six N atoms from three ethyl-enediamine ligands. The P atoms of the anions adopt a distorted tetra-hedral geometry. In the crystal, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the cations and anions into a three-dimensional network.

Related literature

For related structures, see: Amani et al. (2006 ▶); Jun & Zhang (2010 ▶); Rafizadeh & Amani (2006a ▶,b ▶, 2007 ▶); Rafizadeh, Amani & Aghayan (2006 ▶); Rafizadeh, Amani & Broushaky (2006 ▶); Rafizadeh, Hoseinzadeh & Amani (2006 ▶); Rafizadeh et al. (2005 ▶, 2007 ▶, 2009 ▶).

Experimental

Crystal data

[Ni(C2H8N2)3](C2H6O4P)2

M = 489.08

Monoclinic,

a = 9.2553 (5) Å

b = 12.4913 (5) Å

c = 18.190 (1) Å

β = 90.156 (4)°

V = 2102.95 (18) Å3

Z = 4

Mo Kα radiation

μ = 1.12 mm−1

T = 120 K

0.49 × 0.40 × 0.38 mm

Data collection

Stoe IPDS-2T diffractometer

Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002 ▶) T min = 0.590, T max = 0.650

9338 measured reflections

5205 independent reflections

4555 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.085

S = 1.08

5205 reflections

284 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.40 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029984/hy2566sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029984/hy2566Isup2.hkl

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

[Ni(C2H8N2)3](C2H6O4P)2	F(000) = 1040
Mr = 489.08	Dx = 1.545 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9338 reflections
a = 9.2553 (5) Å	θ = 2.7–29.2°
b = 12.4913 (5) Å	µ = 1.12 mm−1
c = 18.190 (1) Å	T = 120 K
β = 90.156 (4)°	Block, violet
V = 2102.95 (18) Å3	0.49 × 0.40 × 0.38 mm
Z = 4

Stoe IPDS-2T diffractometer	5205 independent reflections
Radiation source: fine-focus sealed tube	4555 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 0.15 pixels mm-1	θmax = 29.2°, θmin = 2.7°
ω scans	h = −12→10
Absorption correction: numerical (X-SHAPE and X-RED; Stoe & Cie, 2002)	k = −17→14
Tmin = 0.590, Tmax = 0.650	l = −21→24
9338 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0434P)2 + 1.1522P] where P = (Fo2 + 2Fc2)/3
5205 reflections	(Δ/σ)max = 0.014
284 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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
C1	0.7792 (2)	0.35678 (14)	0.35218 (10)	0.0138 (3)
H1A	0.8421	0.2961	0.3434	0.017*
H1B	0.6870	0.3428	0.3286	0.017*
C2	0.7579 (2)	0.37245 (14)	0.43420 (10)	0.0142 (4)
H2A	0.7108	0.3102	0.4552	0.017*
H2B	0.8506	0.3818	0.4583	0.017*
C3	0.4548 (2)	0.69465 (15)	0.39362 (11)	0.0158 (4)
H3A	0.4030	0.7614	0.4005	0.019*
H3B	0.4050	0.6391	0.4209	0.019*
C4	0.4576 (2)	0.66600 (16)	0.31238 (10)	0.0162 (4)
H4A	0.3602	0.6530	0.2948	0.019*
H4B	0.4984	0.7246	0.2843	0.019*
C5	0.9829 (2)	0.72847 (15)	0.40027 (11)	0.0178 (4)
H5A	1.0827	0.7361	0.4159	0.021*
H5B	0.9296	0.7907	0.4169	0.021*
C6	0.9750 (2)	0.72044 (16)	0.31718 (11)	0.0186 (4)
H6A	1.0093	0.7863	0.2951	0.022*
H6B	1.0355	0.6621	0.3001	0.022*
C7	0.6815 (3)	0.55279 (17)	−0.01227 (11)	0.0242 (4)
H7A	0.7315	0.6196	−0.0064	0.029*
H7B	0.5815	0.5621	0.0001	0.029*
H7C	0.6891	0.5295	−0.0624	0.029*
C8	0.9788 (3)	0.61156 (19)	0.10517 (15)	0.0301 (5)
H8A	0.9829	0.5941	0.0538	0.036*
H8B	1.0351	0.5608	0.1326	0.036*
H8C	1.0169	0.6822	0.1128	0.036*
C9	0.8392 (3)	0.79999 (16)	0.61676 (13)	0.0242 (5)
H9A	0.7931	0.8165	0.6626	0.029*
H9B	0.7737	0.8144	0.5770	0.029*
H9C	0.9242	0.8434	0.6114	0.029*
C10	0.7784 (3)	0.56998 (19)	0.76650 (11)	0.0250 (5)
H10A	0.8726	0.6021	0.7677	0.030*
H10B	0.7877	0.4939	0.7607	0.030*
H10C	0.7290	0.5852	0.8116	0.030*
N1	0.84434 (19)	0.45511 (12)	0.32143 (9)	0.0126 (3)
H1C	0.837 (3)	0.449 (2)	0.2723 (16)	0.022 (6)*
H1D	0.940 (4)	0.456 (3)	0.3362 (18)	0.042 (9)*
N2	0.66754 (19)	0.46838 (12)	0.44496 (9)	0.0118 (3)
H2C	0.682 (3)	0.491 (2)	0.4897 (16)	0.024 (7)*
H2D	0.581 (3)	0.451 (2)	0.4390 (16)	0.026 (7)*
N3	0.60386 (18)	0.70561 (12)	0.42125 (9)	0.0130 (3)
H3C	0.636 (3)	0.773 (2)	0.4098 (14)	0.019 (6)*
H3D	0.606 (3)	0.696 (2)	0.4703 (15)	0.019 (6)*
N4	0.54660 (18)	0.56862 (13)	0.30284 (9)	0.0136 (3)
H4C	0.565 (3)	0.557 (2)	0.2541 (17)	0.029 (7)*
H4D	0.495 (3)	0.512 (2)	0.3150 (15)	0.025 (7)*
N5	0.92017 (18)	0.63031 (13)	0.43245 (9)	0.0133 (3)
H5C	0.981 (3)	0.578 (2)	0.4283 (15)	0.021 (7)*
H5D	0.903 (3)	0.638 (2)	0.4756 (15)	0.020 (6)*
N6	0.82331 (18)	0.70111 (12)	0.29583 (9)	0.0135 (3)
H6C	0.8192	0.6762	0.2495	0.016*
H6D	0.7729	0.7627	0.2979	0.016*
O1	0.59564 (17)	0.52152 (13)	0.14823 (8)	0.0218 (3)
O2	0.82725 (16)	0.40819 (10)	0.15670 (7)	0.0163 (3)
O3	0.74502 (17)	0.47356 (11)	0.03552 (7)	0.0173 (3)
O4	0.83165 (17)	0.60793 (11)	0.12947 (8)	0.0185 (3)
O5	0.83257 (17)	0.49601 (11)	0.61469 (8)	0.0210 (3)
O6	0.62989 (16)	0.62537 (11)	0.57626 (8)	0.0171 (3)
O7	0.87916 (16)	0.68872 (11)	0.61572 (8)	0.0182 (3)
O8	0.69760 (16)	0.61289 (11)	0.70610 (7)	0.0176 (3)
P1	0.74375 (5)	0.49734 (4)	0.12224 (2)	0.01149 (10)
P2	0.75573 (5)	0.59976 (4)	0.62379 (2)	0.01087 (10)
Ni1	0.73359 (2)	0.587559 (17)	0.369019 (12)	0.00877 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0156 (9)	0.0121 (8)	0.0136 (8)	0.0000 (6)	−0.0006 (7)	−0.0019 (6)
C2	0.0162 (9)	0.0140 (8)	0.0124 (8)	0.0002 (7)	−0.0028 (7)	0.0014 (6)
C3	0.0129 (9)	0.0195 (9)	0.0149 (8)	0.0036 (7)	0.0019 (8)	0.0002 (7)
C4	0.0121 (9)	0.0218 (9)	0.0147 (8)	0.0028 (7)	−0.0018 (8)	0.0016 (7)
C5	0.0148 (9)	0.0152 (8)	0.0235 (10)	−0.0036 (7)	−0.0054 (8)	−0.0002 (7)
C6	0.0146 (9)	0.0205 (9)	0.0209 (9)	−0.0031 (7)	0.0030 (8)	0.0054 (7)
C7	0.0346 (13)	0.0236 (10)	0.0144 (9)	−0.0012 (9)	−0.0034 (9)	0.0051 (7)
C8	0.0210 (11)	0.0258 (11)	0.0435 (14)	−0.0081 (9)	−0.0027 (11)	0.0073 (10)
C9	0.0250 (11)	0.0149 (9)	0.0328 (11)	−0.0060 (8)	−0.0085 (10)	0.0026 (8)
C10	0.0312 (13)	0.0319 (11)	0.0118 (9)	0.0004 (9)	−0.0040 (9)	0.0039 (8)
N1	0.0143 (8)	0.0147 (7)	0.0088 (7)	−0.0001 (6)	−0.0005 (7)	−0.0010 (5)
N2	0.0132 (8)	0.0122 (7)	0.0101 (7)	−0.0021 (6)	0.0008 (7)	−0.0006 (5)
N3	0.0140 (8)	0.0135 (7)	0.0115 (7)	0.0008 (6)	0.0008 (6)	0.0006 (5)
N4	0.0118 (7)	0.0172 (7)	0.0120 (7)	−0.0008 (6)	0.0009 (6)	−0.0006 (6)
N5	0.0122 (8)	0.0167 (7)	0.0109 (7)	0.0002 (6)	−0.0007 (6)	−0.0017 (6)
N6	0.0149 (8)	0.0135 (7)	0.0121 (7)	−0.0005 (5)	0.0008 (7)	0.0012 (5)
O1	0.0172 (7)	0.0314 (8)	0.0168 (7)	0.0059 (6)	0.0028 (6)	0.0006 (6)
O2	0.0215 (7)	0.0128 (6)	0.0145 (6)	0.0022 (5)	−0.0014 (6)	0.0010 (5)
O3	0.0269 (8)	0.0160 (6)	0.0089 (6)	0.0010 (5)	−0.0006 (6)	−0.0001 (5)
O4	0.0225 (8)	0.0123 (6)	0.0206 (7)	−0.0010 (5)	−0.0036 (6)	−0.0013 (5)
O5	0.0211 (7)	0.0174 (7)	0.0244 (7)	0.0039 (6)	0.0023 (7)	−0.0039 (5)
O6	0.0147 (7)	0.0219 (7)	0.0147 (6)	−0.0020 (5)	−0.0037 (6)	0.0006 (5)
O7	0.0129 (7)	0.0181 (6)	0.0236 (7)	−0.0030 (5)	−0.0005 (6)	0.0022 (5)
O8	0.0187 (7)	0.0240 (7)	0.0101 (6)	0.0038 (5)	0.0024 (6)	0.0011 (5)
P1	0.0146 (2)	0.0111 (2)	0.00880 (19)	0.00133 (16)	−0.00036 (18)	−0.00062 (15)
P2	0.0095 (2)	0.0136 (2)	0.0095 (2)	−0.00065 (15)	0.00064 (18)	−0.00094 (15)
Ni1	0.00858 (12)	0.00985 (11)	0.00788 (11)	−0.00036 (8)	0.00025 (9)	0.00034 (7)

C1—N1	1.479 (2)	C9—H9C	0.9600
C1—C2	1.518 (2)	C10—O8	1.431 (3)
C1—H1A	0.9700	C10—H10A	0.9600
C1—H1B	0.9700	C10—H10B	0.9600
C2—N2	1.475 (2)	C10—H10C	0.9600
C2—H2A	0.9700	N1—Ni1	2.1313 (15)
C2—H2B	0.9700	N1—H1C	0.90 (3)
C3—N3	1.474 (3)	N1—H1D	0.93 (4)
C3—C4	1.521 (3)	N2—Ni1	2.1220 (15)
C3—H3A	0.9700	N2—H2C	0.87 (3)
C3—H3B	0.9700	N2—H2D	0.83 (3)
C4—N4	1.479 (2)	N3—Ni1	2.1272 (15)
C4—H4A	0.9700	N3—H3C	0.92 (3)
C4—H4B	0.9700	N3—H3D	0.90 (3)
C5—N5	1.478 (2)	N4—Ni1	2.1187 (18)
C5—C6	1.516 (3)	N4—H4C	0.91 (3)
C5—H5A	0.9700	N4—H4D	0.89 (3)
C5—H5B	0.9700	N5—Ni1	2.1418 (18)
C6—N6	1.476 (3)	N5—H5C	0.86 (3)
C6—H6A	0.9700	N5—H5D	0.81 (3)
C6—H6B	0.9700	N6—Ni1	2.1166 (15)
C7—O3	1.442 (2)	N6—H6C	0.9000
C7—H7A	0.9600	N6—H6D	0.9000
C7—H7B	0.9600	O1—P1	1.4824 (15)
C7—H7C	0.9600	O2—P1	1.4925 (14)
C8—O4	1.434 (3)	O3—P1	1.6052 (14)
C8—H8A	0.9600	O4—P1	1.6084 (14)
C8—H8B	0.9600	O5—P2	1.4878 (14)
C8—H8C	0.9600	O6—P2	1.4835 (16)
C9—O7	1.438 (2)	O7—P2	1.6008 (14)
C9—H9A	0.9600	O8—P2	1.6008 (13)
C9—H9B	0.9600
N1—C1—C2	108.59 (14)	Ni1—N1—H1D	109 (2)
N1—C1—H1A	110.0	H1C—N1—H1D	111 (3)
C2—C1—H1A	110.0	C2—N2—Ni1	108.62 (11)
N1—C1—H1B	110.0	C2—N2—H2C	107.3 (19)
C2—C1—H1B	110.0	Ni1—N2—H2C	109.7 (18)
H1A—C1—H1B	108.4	C2—N2—H2D	108.2 (19)
N2—C2—C1	108.08 (15)	Ni1—N2—H2D	112 (2)
N2—C2—H2A	110.1	H2C—N2—H2D	111 (3)
C1—C2—H2A	110.1	C3—N3—Ni1	108.20 (11)
N2—C2—H2B	110.1	C3—N3—H3C	108.0 (17)
C1—C2—H2B	110.1	Ni1—N3—H3C	110.7 (16)
H2A—C2—H2B	108.4	C3—N3—H3D	109.8 (17)
N3—C3—C4	109.55 (15)	Ni1—N3—H3D	109.7 (16)
N3—C3—H3A	109.8	H3C—N3—H3D	110 (2)
C4—C3—H3A	109.8	C4—N4—Ni1	107.20 (12)
N3—C3—H3B	109.8	C4—N4—H4C	110.2 (19)
C4—C3—H3B	109.8	Ni1—N4—H4C	115 (2)
H3A—C3—H3B	108.2	C4—N4—H4D	109.3 (17)
N4—C4—C3	108.57 (16)	Ni1—N4—H4D	112.8 (19)
N4—C4—H4A	110.0	H4C—N4—H4D	103 (2)
C3—C4—H4A	110.0	C5—N5—Ni1	108.09 (12)
N4—C4—H4B	110.0	C5—N5—H5C	109.6 (18)
C3—C4—H4B	110.0	Ni1—N5—H5C	106.7 (19)
H4A—C4—H4B	108.4	C5—N5—H5D	111.3 (19)
N5—C5—C6	108.79 (16)	Ni1—N5—H5D	113 (2)
N5—C5—H5A	109.9	H5C—N5—H5D	108 (3)
C6—C5—H5A	109.9	C6—N6—Ni1	108.58 (12)
N5—C5—H5B	109.9	C6—N6—H6C	110.0
C6—C5—H5B	109.9	Ni1—N6—H6C	110.0
H5A—C5—H5B	108.3	C6—N6—H6D	110.0
N6—C6—C5	108.44 (15)	Ni1—N6—H6D	110.0
N6—C6—H6A	110.0	H6C—N6—H6D	108.4
C5—C6—H6A	110.0	C7—O3—P1	117.49 (12)
N6—C6—H6B	110.0	C8—O4—P1	118.86 (13)
C5—C6—H6B	110.0	C9—O7—P2	119.09 (13)
H6A—C6—H6B	108.4	C10—O8—P2	120.22 (13)
O3—C7—H7A	109.5	O1—P1—O2	119.76 (8)
O3—C7—H7B	109.5	O1—P1—O3	111.12 (9)
H7A—C7—H7B	109.5	O2—P1—O3	105.64 (8)
O3—C7—H7C	109.5	O1—P1—O4	105.48 (9)
H7A—C7—H7C	109.5	O2—P1—O4	110.20 (8)
H7B—C7—H7C	109.5	O3—P1—O4	103.54 (8)
O4—C8—H8A	109.5	O6—P2—O5	119.85 (9)
O4—C8—H8B	109.5	O6—P2—O7	110.87 (8)
H8A—C8—H8B	109.5	O5—P2—O7	104.66 (8)
O4—C8—H8C	109.5	O6—P2—O8	104.94 (8)
H8A—C8—H8C	109.5	O5—P2—O8	110.81 (8)
H8B—C8—H8C	109.5	O7—P2—O8	104.86 (8)
O7—C9—H9A	109.5	N6—Ni1—N4	92.22 (6)
O7—C9—H9B	109.5	N6—Ni1—N2	173.64 (7)
H9A—C9—H9B	109.5	N4—Ni1—N2	93.17 (7)
O7—C9—H9C	109.5	N6—Ni1—N3	92.25 (6)
H9A—C9—H9C	109.5	N4—Ni1—N3	82.53 (6)
H9B—C9—H9C	109.5	N2—Ni1—N3	91.81 (6)
O8—C10—H10A	109.5	N6—Ni1—N1	94.29 (6)
O8—C10—H10B	109.5	N4—Ni1—N1	94.33 (6)
H10A—C10—H10B	109.5	N2—Ni1—N1	81.93 (6)
O8—C10—H10C	109.5	N3—Ni1—N1	172.86 (6)
H10A—C10—H10C	109.5	N6—Ni1—N5	81.64 (6)
H10B—C10—H10C	109.5	N4—Ni1—N5	171.90 (6)
C1—N1—Ni1	107.09 (11)	N2—Ni1—N5	93.30 (7)
C1—N1—H1C	105.9 (17)	N3—Ni1—N5	92.40 (7)
Ni1—N1—H1C	116.1 (17)	N1—Ni1—N5	91.40 (7)
C1—N1—H1D	107 (2)
N1—C1—C2—N2	56.9 (2)	C6—N6—Ni1—N1	−74.78 (13)
N3—C3—C4—N4	55.1 (2)	C6—N6—Ni1—N5	16.01 (12)
N5—C5—C6—N6	55.6 (2)	C4—N4—Ni1—N6	−73.62 (11)
C2—C1—N1—Ni1	−43.53 (17)	C4—N4—Ni1—N2	109.78 (11)
C1—C2—N2—Ni1	−40.33 (18)	C4—N4—Ni1—N3	18.36 (11)
C4—C3—N3—Ni1	−37.22 (17)	C4—N4—Ni1—N1	−168.09 (11)
C3—C4—N4—Ni1	−43.55 (17)	C2—N2—Ni1—N4	107.14 (13)
C6—C5—N5—Ni1	−39.95 (18)	C2—N2—Ni1—N3	−170.24 (13)
C5—C6—N6—Ni1	−42.24 (17)	C2—N2—Ni1—N1	13.21 (13)
C7—O3—P1—O1	53.70 (17)	C2—N2—Ni1—N5	−77.74 (13)
C7—O3—P1—O2	−174.96 (15)	C3—N3—Ni1—N6	102.42 (12)
C7—O3—P1—O4	−59.09 (16)	C3—N3—Ni1—N4	10.48 (12)
C8—O4—P1—O1	−177.29 (16)	C3—N3—Ni1—N2	−82.48 (12)
C8—O4—P1—O2	52.12 (18)	C3—N3—Ni1—N5	−175.86 (12)
C8—O4—P1—O3	−60.47 (18)	C1—N1—Ni1—N6	−168.38 (12)
C9—O7—P2—O6	45.21 (17)	C1—N1—Ni1—N4	−75.83 (12)
C9—O7—P2—O5	175.78 (15)	C1—N1—Ni1—N2	16.76 (12)
C9—O7—P2—O8	−67.52 (17)	C1—N1—Ni1—N5	109.90 (12)
C10—O8—P2—O6	164.87 (15)	C5—N5—Ni1—N6	13.37 (12)
C10—O8—P2—O5	34.15 (18)	C5—N5—Ni1—N2	−170.51 (12)
C10—O8—P2—O7	−78.24 (16)	C5—N5—Ni1—N3	−78.56 (12)
C6—N6—Ni1—N4	−169.29 (12)	C5—N5—Ni1—N1	107.49 (12)
C6—N6—Ni1—N3	108.10 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O2	0.90 (3)	2.17 (3)	3.057 (2)	171 (2)
N1—H1D···O5i	0.93 (4)	2.36 (4)	3.263 (2)	165 (3)
N2—H2C···O6	0.87 (3)	2.35 (3)	3.111 (2)	146 (2)
N2—H2D···O6ii	0.84 (3)	2.19 (3)	3.015 (2)	169 (2)
N3—H3C···O2iii	0.92 (3)	2.11 (3)	2.971 (2)	157 (2)
N3—H3D···O6	0.90 (3)	2.13 (3)	3.002 (2)	163 (2)
N4—H4C···O1	0.92 (3)	2.00 (3)	2.910 (2)	176 (3)
N4—H4D···O8ii	0.88 (3)	2.40 (3)	3.205 (2)	152 (2)
N5—H5C···O5i	0.87 (3)	2.11 (3)	2.911 (2)	154 (2)
N6—H6C···O4	0.90	2.35	3.243 (2)	175
N6—H6D···O2iii	0.90	2.20	3.064 (2)	160
C9—H9C···O1iv	0.96	2.41	3.305 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O2	0.90 (3)	2.17 (3)	3.057 (2)	171 (2)
N1—H1D⋯O5i	0.93 (4)	2.36 (4)	3.263 (2)	165 (3)
N2—H2C⋯O6	0.87 (3)	2.35 (3)	3.111 (2)	146 (2)
N2—H2D⋯O6ii	0.84 (3)	2.19 (3)	3.015 (2)	169 (2)
N3—H3C⋯O2iii	0.92 (3)	2.11 (3)	2.971 (2)	157 (2)
N3—H3D⋯O6	0.90 (3)	2.13 (3)	3.002 (2)	163 (2)
N4—H4C⋯O1	0.92 (3)	2.00 (3)	2.910 (2)	176 (3)
N4—H4D⋯O8ii	0.88 (3)	2.40 (3)	3.205 (2)	152 (2)
N5—H5C⋯O5i	0.87 (3)	2.11 (3)	2.911 (2)	154 (2)
N6—H6C⋯O4	0.90	2.35	3.243 (2)	175
N6—H6D⋯O2iii	0.90	2.20	3.064 (2)	160
C9—H9C⋯O1iv	0.96	2.41	3.305 (3)	155

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