[N,N,N′-Tris(3-amino­prop­yl)ethyl­enediamine-κ5N]nickel bis­(perchlorate)

Xu, T.-T.; Xu, X.-Y.; Wang, D.-Q.; Gao, J.; Lu, L.-D.

doi:10.1107/S1600536806024330

[N,N,N′-Tris(3-aminopropyl)ethylenediamine-κ⁵N]nickel bis(perchlorate)

T.-T. Xu, X.-Y. Xu, D.-Q. Wang, J. Gao and L.-D. Lu

The asymmetric unit of the title complex, [Ni(C₁₁H₂₉N₅)](ClO₄)₂, consists of an [Ni(C₁₁H₂₉N₅)]²⁺ cation and two uncoordinated perchlorate anions. The Ni^II atom is five-coordinated in a slightly distorted square-pyramidal geometry, with four of the N atoms forming the basal plane and the fifth N atom in the apical position. The complex shows a three-dimensional network structure assembled by intermolecular hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024330/ww2017sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024330/ww2017Isup2.hkl Contains datablock I

CCDC reference: 613848

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.015 Å
Disorder in solvent or counterion
R factor = 0.064
wR factor = 0.131
Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         34 Perc.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.120
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Ni1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      41.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         15
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  CL1     ..       2.95 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B    ..  O6'     ..       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4B    ..  O5      ..       2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B    ..  CL2     ..       2.94 Ang.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

[N,N,N'-Tris(3-aminopropyl)ethylenediamine-κ⁵N]nickel bis(perchlorate) top

Crystal data top

[Ni(C₁₁H₂₉N₅)](ClO₄)₂	F(000) = 1024
M_r = 489.00	D_x = 1.627 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 882 reflections
a = 9.454 (4) Å	θ = 2.6–15.9°
b = 14.589 (7) Å	µ = 1.29 mm⁻¹
c = 14.477 (7) Å	T = 298 K
β = 90.285 (8)°	Block, blue–purple
V = 1996.6 (16) Å³	0.42 × 0.30 × 0.19 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3526 independent reflections
Radiation source: fine-focus sealed tube	1216 reflections with I > σ(I)
Graphite monochromator	R_int = 0.120
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.614, T_max = 0.792	k = −17→11
10278 measured reflections	l = −17→16

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0268P)²] where P = (F_o² + 2F_c²)/3
3526 reflections	(Δ/σ)_max < 0.001
309 parameters	Δρ_max = 0.48 e Å⁻³
655 restraints	Δρ_min = −0.41 e Å⁻³

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 > 2σ(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	Occ. (<1)
Ni1	0.27513 (10)	0.22865 (7)	0.41737 (7)	0.0534 (4)
Cl1	0.2966 (3)	0.20870 (19)	0.12416 (17)	0.0691 (7)
Cl2	0.3749 (3)	0.0277 (2)	0.65403 (19)	0.0765 (8)
N1	0.2535 (7)	0.0906 (4)	0.3952 (5)	0.085 (2)
H1A	0.2965	0.0776	0.3414	0.102*
H1B	0.3023	0.0616	0.4400	0.102*
N2	0.0920 (7)	0.2547 (5)	0.3447 (5)	0.078 (2)
H2	0.1191	0.2547	0.2844	0.093*
N3	0.3067 (8)	0.3694 (5)	0.4042 (5)	0.073 (2)
N4	0.4817 (6)	0.2105 (4)	0.4505 (4)	0.069 (2)
H4A	0.4992	0.2378	0.5051	0.083*
H4B	0.4984	0.1502	0.4574	0.083*
N5	0.1922 (6)	0.2329 (4)	0.5452 (4)	0.070 (2)
H5A	0.0976	0.2370	0.5388	0.083*
H5B	0.2104	0.1786	0.5723	0.083*
O1	0.153 (2)	0.178 (2)	0.1141 (18)	0.092 (6)	0.44 (4)
O2	0.302 (4)	0.2993 (17)	0.106 (2)	0.130 (7)	0.44 (4)
O3	0.377 (3)	0.165 (2)	0.0593 (17)	0.112 (7)	0.44 (4)
O1'	0.368 (2)	0.2862 (13)	0.0877 (13)	0.108 (5)	0.56 (4)
O2'	0.327 (3)	0.1328 (12)	0.0672 (13)	0.114 (6)	0.56 (4)
O3'	0.1498 (13)	0.225 (2)	0.1266 (12)	0.094 (5)	0.56 (4)
O4	0.3413 (6)	0.1918 (5)	0.2145 (4)	0.118 (2)
O5	0.4709 (13)	0.0972 (10)	0.6320 (8)	0.142 (4)	0.743 (9)
O6	0.4428 (14)	−0.0327 (7)	0.7138 (8)	0.131 (4)	0.743 (9)
O7	0.3495 (14)	−0.0190 (8)	0.5722 (7)	0.141 (4)	0.743 (9)
O8	0.2616 (11)	0.0655 (8)	0.6948 (8)	0.133 (4)	0.743 (9)
O5'	0.269 (2)	0.0154 (19)	0.5840 (16)	0.110 (7)	0.257 (9)
O6'	0.5088 (18)	0.011 (2)	0.626 (2)	0.141 (8)	0.257 (9)
O7'	0.334 (3)	−0.019 (2)	0.7331 (14)	0.113 (7)	0.257 (9)
O8'	0.366 (4)	0.1261 (11)	0.6757 (18)	0.115 (7)	0.257 (9)
C1	0.1111 (11)	0.0493 (6)	0.3915 (7)	0.098 (3)
H1C	0.1196	−0.0145	0.3735	0.118*
H1D	0.0701	0.0510	0.4527	0.118*
C2	0.0148 (10)	0.0960 (8)	0.3265 (7)	0.111 (3)
H2A	0.0577	0.0947	0.2658	0.133*
H2B	−0.0721	0.0607	0.3228	0.133*
C3	−0.0223 (10)	0.1914 (7)	0.3479 (7)	0.100 (3)
H3A	−0.0946	0.2114	0.3047	0.120*
H3B	−0.0630	0.1933	0.4093	0.120*
C4	0.0569 (9)	0.3514 (7)	0.3643 (6)	0.092 (3)
H4C	−0.0144	0.3727	0.3209	0.111*
H4D	0.0189	0.3567	0.4261	0.111*
C5	0.1822 (11)	0.4069 (7)	0.3563 (6)	0.097 (3)
H5C	0.1623	0.4673	0.3810	0.116*
H5D	0.2044	0.4140	0.2914	0.116*
C6	0.4351 (13)	0.3893 (6)	0.3442 (6)	0.096 (4)
H6A	0.4159	0.3669	0.2823	0.115*
H6B	0.4469	0.4553	0.3402	0.115*
C7	0.5715 (11)	0.3482 (9)	0.3773 (7)	0.107 (4)
H7A	0.6464	0.3695	0.3371	0.128*
H7B	0.5912	0.3721	0.4386	0.128*
C8	0.5794 (10)	0.2472 (7)	0.3818 (6)	0.089 (3)
H8A	0.5565	0.2218	0.3216	0.107*
H8B	0.6752	0.2289	0.3974	0.107*
C9	0.3289 (10)	0.4193 (6)	0.4932 (7)	0.089 (3)
H9A	0.3255	0.4846	0.4805	0.107*
H9B	0.4235	0.4055	0.5155	0.107*
C10	0.2266 (11)	0.3990 (7)	0.5692 (7)	0.096 (3)
H10A	0.1315	0.4081	0.5456	0.116*
H10B	0.2416	0.4432	0.6184	0.116*
C11	0.2360 (10)	0.3044 (7)	0.6098 (6)	0.087 (3)
H11A	0.3327	0.2929	0.6292	0.104*
H11B	0.1767	0.3015	0.6642	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0412 (6)	0.0583 (7)	0.0608 (7)	−0.0036 (6)	0.0004 (5)	−0.0026 (6)
Cl1	0.0592 (18)	0.085 (2)	0.0629 (17)	0.0027 (17)	0.0081 (14)	0.0086 (16)
Cl2	0.077 (2)	0.081 (2)	0.071 (2)	0.0016 (18)	0.0050 (16)	−0.0032 (17)
N1	0.080 (5)	0.094 (5)	0.081 (5)	−0.015 (4)	0.006 (4)	−0.003 (4)
N2	0.054 (4)	0.097 (5)	0.082 (4)	−0.019 (4)	−0.012 (4)	−0.018 (4)
N3	0.078 (5)	0.076 (5)	0.064 (5)	−0.001 (4)	−0.021 (5)	0.002 (4)
N4	0.062 (5)	0.074 (6)	0.072 (5)	0.003 (4)	0.010 (4)	−0.011 (4)
N5	0.061 (5)	0.068 (5)	0.079 (5)	−0.010 (4)	−0.007 (4)	0.003 (5)
O1	0.052 (9)	0.110 (12)	0.114 (10)	−0.014 (9)	−0.009 (8)	0.007 (10)
O2	0.120 (14)	0.107 (12)	0.165 (13)	−0.012 (11)	0.044 (12)	0.023 (11)
O3	0.089 (12)	0.132 (14)	0.117 (11)	−0.028 (11)	0.065 (10)	−0.032 (11)
O1'	0.080 (10)	0.099 (10)	0.146 (10)	−0.017 (9)	0.062 (8)	0.038 (8)
O2'	0.115 (12)	0.101 (11)	0.127 (10)	−0.019 (9)	0.039 (9)	−0.038 (9)
O3'	0.044 (7)	0.134 (12)	0.103 (8)	0.026 (8)	0.009 (6)	0.011 (9)
O4	0.085 (5)	0.187 (6)	0.082 (5)	0.010 (4)	−0.011 (4)	0.036 (4)
O5	0.124 (9)	0.147 (9)	0.154 (9)	−0.044 (8)	0.034 (7)	0.046 (8)
O6	0.154 (10)	0.124 (8)	0.115 (8)	0.032 (8)	0.000 (8)	0.044 (7)
O7	0.171 (10)	0.156 (9)	0.094 (7)	0.038 (7)	−0.032 (7)	−0.054 (6)
O8	0.101 (8)	0.113 (8)	0.185 (9)	0.024 (7)	0.074 (7)	−0.038 (7)
O5'	0.094 (13)	0.124 (13)	0.110 (12)	−0.021 (12)	−0.007 (12)	0.016 (12)
O6'	0.106 (14)	0.142 (14)	0.174 (14)	0.006 (13)	0.056 (13)	−0.009 (14)
O7'	0.121 (14)	0.114 (13)	0.104 (13)	−0.026 (13)	0.026 (13)	0.049 (12)
O8'	0.127 (14)	0.109 (14)	0.108 (13)	0.024 (13)	0.014 (13)	−0.016 (12)
C1	0.111 (7)	0.084 (6)	0.100 (6)	−0.043 (6)	0.017 (6)	−0.005 (5)
C2	0.077 (6)	0.136 (7)	0.120 (6)	−0.045 (6)	0.005 (5)	−0.020 (6)
C3	0.070 (5)	0.131 (7)	0.100 (6)	−0.017 (6)	0.005 (5)	−0.016 (6)
C4	0.068 (6)	0.121 (7)	0.088 (6)	0.025 (6)	−0.022 (5)	−0.001 (6)
C5	0.104 (7)	0.093 (6)	0.093 (6)	0.007 (6)	−0.030 (6)	−0.004 (5)
C6	0.163 (12)	0.060 (7)	0.065 (7)	−0.038 (8)	−0.018 (8)	0.012 (6)
C7	0.086 (9)	0.156 (13)	0.077 (8)	−0.048 (10)	0.018 (7)	−0.011 (8)
C8	0.056 (7)	0.124 (10)	0.088 (8)	−0.011 (7)	−0.003 (6)	−0.029 (8)
C9	0.095 (9)	0.058 (7)	0.114 (9)	0.001 (6)	−0.009 (7)	−0.027 (7)
C10	0.099 (9)	0.094 (9)	0.097 (9)	0.005 (8)	0.015 (7)	−0.047 (7)
C11	0.093 (8)	0.110 (9)	0.058 (7)	−0.011 (7)	0.008 (6)	−0.006 (7)

Geometric parameters (Å, º) top

Ni1—N5	2.015 (6)	N5—C11	1.459 (9)
Ni1—N4	2.026 (6)	N5—H5A	0.9000
Ni1—N1	2.049 (6)	N5—H5B	0.9000
Ni1—N2	2.058 (6)	C1—C2	1.472 (11)
Ni1—N3	2.084 (7)	C1—H1C	0.9700
Cl1—O2	1.35 (2)	C1—H1D	0.9700
Cl1—O3	1.37 (2)	C2—C3	1.470 (11)
Cl1—O4	1.394 (6)	C2—H2A	0.9700
Cl1—O3'	1.410 (11)	C2—H2B	0.9700
Cl1—O2'	1.411 (12)	C3—H3A	0.9700
Cl1—O1'	1.422 (11)	C3—H3B	0.9700
Cl1—O1	1.435 (19)	C4—C5	1.439 (11)
Cl2—O8	1.344 (9)	C4—H4C	0.9700
Cl2—O6'	1.354 (14)	C4—H4D	0.9700
Cl2—O7	1.387 (9)	C5—H5C	0.9700
Cl2—O7'	1.389 (14)	C5—H5D	0.9700
Cl2—O6	1.391 (9)	C6—C7	1.500 (12)
Cl2—O5	1.398 (10)	C6—H6A	0.9700
Cl2—O5'	1.432 (14)	C6—H6B	0.9700
Cl2—O8'	1.471 (14)	C7—C8	1.476 (11)
N1—C1	1.476 (9)	C7—H7A	0.9700
N1—H1A	0.9000	C7—H7B	0.9700
N1—H1B	0.9000	C8—H8A	0.9700
N2—C3	1.422 (10)	C8—H8B	0.9700
N2—C4	1.477 (10)	C9—C10	1.498 (11)
N2—H2	0.9100	C9—H9A	0.9700
N3—C5	1.468 (10)	C9—H9B	0.9700
N3—C9	1.494 (9)	C10—C11	1.502 (10)
N3—C6	1.524 (11)	C10—H10A	0.9700
N4—C8	1.462 (9)	C10—H10B	0.9700
N4—H4A	0.9000	C11—H11A	0.9700
N4—H4B	0.9000	C11—H11B	0.9700

N5—Ni1—N4	99.5 (3)	N2—C3—H3A	108.5
N5—Ni1—N1	97.8 (3)	C2—C3—H3A	108.5
N4—Ni1—N1	90.3 (3)	N2—C3—H3B	108.5
N5—Ni1—N2	97.7 (3)	C2—C3—H3B	108.5
N4—Ni1—N2	162.4 (3)	H3A—C3—H3B	107.5
N1—Ni1—N2	91.0 (3)	C5—C4—N2	109.6 (8)
N5—Ni1—N3	96.3 (3)	C5—C4—H4C	109.7
N4—Ni1—N3	90.7 (3)	N2—C4—H4C	109.7
N1—Ni1—N3	165.5 (3)	C5—C4—H4D	109.7
N2—Ni1—N3	83.8 (3)	N2—C4—H4D	109.7
C1—N1—Ni1	119.8 (6)	H4C—C4—H4D	108.2
C1—N1—H1A	107.4	C4—C5—N3	114.3 (8)
Ni1—N1—H1A	107.4	C4—C5—H5C	108.7
C1—N1—H1B	107.4	N3—C5—H5C	108.7
Ni1—N1—H1B	107.4	C4—C5—H5D	108.7
H1A—N1—H1B	106.9	N3—C5—H5D	108.7
C3—N2—C4	116.3 (8)	H5C—C5—H5D	107.6
C3—N2—Ni1	120.0 (6)	C7—C6—N3	115.3 (8)
C4—N2—Ni1	105.5 (5)	C7—C6—H6A	108.4
C3—N2—H2	104.4	N3—C6—H6A	108.4
C4—N2—H2	104.4	C7—C6—H6B	108.4
Ni1—N2—H2	104.4	N3—C6—H6B	108.4
C5—N3—C9	109.6 (7)	H6A—C6—H6B	107.5
C5—N3—C6	107.4 (8)	C8—C7—C6	117.1 (9)
C9—N3—C6	106.8 (7)	C8—C7—H7A	108.0
C5—N3—Ni1	107.2 (6)	C6—C7—H7A	108.0
C9—N3—Ni1	114.9 (5)	C8—C7—H7B	108.0
C6—N3—Ni1	110.8 (5)	C6—C7—H7B	108.0
C8—N4—Ni1	113.7 (5)	H7A—C7—H7B	107.3
C8—N4—H4A	108.8	N4—C8—C7	111.3 (8)
Ni1—N4—H4A	108.8	N4—C8—H8A	109.4
C8—N4—H4B	108.8	C7—C8—H8A	109.4
Ni1—N4—H4B	108.8	N4—C8—H8B	109.4
H4A—N4—H4B	107.7	C7—C8—H8B	109.4
C11—N5—Ni1	120.0 (5)	H8A—C8—H8B	108.0
C11—N5—H5A	107.3	N3—C9—C10	116.7 (8)
Ni1—N5—H5A	107.3	N3—C9—H9A	108.1
C11—N5—H5B	107.3	C10—C9—H9A	108.1
Ni1—N5—H5B	107.3	N3—C9—H9B	108.1
H5A—N5—H5B	106.9	C10—C9—H9B	108.1
C2—C1—N1	113.3 (8)	H9A—C9—H9B	107.3
C2—C1—H1C	108.9	C9—C10—C11	115.6 (8)
N1—C1—H1C	108.9	C9—C10—H10A	108.4
C2—C1—H1D	108.9	C11—C10—H10A	108.4
N1—C1—H1D	108.9	C9—C10—H10B	108.4
H1C—C1—H1D	107.7	C11—C10—H10B	108.4
C3—C2—C1	116.8 (9)	H10A—C10—H10B	107.4
C3—C2—H2A	108.1	N5—C11—C10	113.0 (7)
C1—C2—H2A	108.1	N5—C11—H11A	109.0
C3—C2—H2B	108.1	C10—C11—H11A	109.0
C1—C2—H2B	108.1	N5—C11—H11B	109.0
H2A—C2—H2B	107.3	C10—C11—H11B	109.0
N2—C3—C2	115.3 (9)	H11A—C11—H11B	107.8

N5—Ni1—N1—C1	63.7 (7)	N4—Ni1—N5—C11	61.2 (6)
N4—Ni1—N1—C1	163.4 (6)	N1—Ni1—N5—C11	152.8 (6)
N2—Ni1—N1—C1	−34.2 (7)	N2—Ni1—N5—C11	−115.1 (6)
N3—Ni1—N1—C1	−102.9 (13)	N3—Ni1—N5—C11	−30.6 (6)
N5—Ni1—N2—C3	−64.0 (7)	Ni1—N1—C1—C2	52.1 (10)
N4—Ni1—N2—C3	128.2 (9)	N1—C1—C2—C3	−64.4 (12)
N1—Ni1—N2—C3	34.0 (7)	C4—N2—C3—C2	178.9 (8)
N3—Ni1—N2—C3	−159.6 (7)	Ni1—N2—C3—C2	−52.0 (11)
N5—Ni1—N2—C4	69.7 (6)	C1—C2—C3—N2	65.3 (12)
N4—Ni1—N2—C4	−98.1 (10)	C3—N2—C4—C5	−178.8 (8)
N1—Ni1—N2—C4	167.7 (6)	Ni1—N2—C4—C5	45.5 (9)
N3—Ni1—N2—C4	−25.8 (6)	N2—C4—C5—N3	−47.2 (11)
N5—Ni1—N3—C5	−94.5 (6)	C9—N3—C5—C4	−102.1 (10)
N4—Ni1—N3—C5	165.8 (6)	C6—N3—C5—C4	142.3 (8)
N1—Ni1—N3—C5	72.1 (14)	Ni1—N3—C5—C4	23.2 (10)
N2—Ni1—N3—C5	2.6 (6)	C5—N3—C6—C7	−174.4 (8)
N5—Ni1—N3—C9	27.5 (6)	C9—N3—C6—C7	68.2 (10)
N4—Ni1—N3—C9	−72.2 (6)	Ni1—N3—C6—C7	−57.6 (9)
N1—Ni1—N3—C9	−165.9 (10)	N3—C6—C7—C8	62.6 (12)
N2—Ni1—N3—C9	124.6 (6)	Ni1—N4—C8—C7	66.9 (9)
N5—Ni1—N3—C6	148.6 (6)	C6—C7—C8—N4	−65.3 (12)
N4—Ni1—N3—C6	48.9 (6)	C5—N3—C9—C10	72.8 (10)
N1—Ni1—N3—C6	−44.7 (14)	C6—N3—C9—C10	−171.2 (8)
N2—Ni1—N3—C6	−114.3 (6)	Ni1—N3—C9—C10	−47.9 (10)
N5—Ni1—N4—C8	−152.0 (6)	N3—C9—C10—C11	68.4 (11)
N1—Ni1—N4—C8	110.1 (6)	Ni1—N5—C11—C10	50.8 (10)
N2—Ni1—N4—C8	15.8 (12)	C9—C10—C11—N5	−67.6 (11)
N3—Ni1—N4—C8	−55.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.90	2.52	3.119 (9)	125
N1—H1B···O5′	0.90	2.22	2.95 (2)	138
N1—H1B···O7	0.90	2.29	3.150 (13)	160
N2—H2···O3′	0.91	2.34	3.24 (2)	166
N2—H2···O4	0.91	2.51	3.161 (10)	129
N2—H2···Cl1	0.91	2.95	3.801 (8)	157
N4—H4A···O3′ⁱ	0.90	2.32	3.140 (17)	151
N4—H4A···O1ⁱ	0.90	2.47	3.29 (3)	153
N4—H4B···O7ⁱⁱ	0.90	2.43	3.235 (13)	149
N4—H4B···O6′ⁱⁱ	0.90	2.64	3.42 (3)	145
N4—H4B···O5	0.90	2.66	3.107 (12)	112
N5—H5A···O1′ⁱⁱⁱ	0.90	2.31	3.14 (2)	153
N5—H5A···O3ⁱⁱⁱ	0.90	2.54	3.33 (3)	147
N5—H5B···O8′	0.90	2.23	2.95 (2)	136
N5—H5B···O5′	0.90	2.45	3.30 (3)	158
N5—H5B···O8	0.90	2.47	3.328 (14)	160
N5—H5B···Cl2	0.90	2.94	3.794 (7)	159

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

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[N,N,N′-Tris(3-amino­prop­yl)ethyl­enediamine-κ5N]nickel bis­(perchlorate)

Supporting information

Key indicators

checkCIF/PLATON results

[N,N,N′-Tris(3-aminopropyl)ethylenediamine-κ⁵N]nickel bis(perchlorate)