The first-row transition-metal series of tris­(ethyl­enedi­amine) di­acetate complexes [M(en)₃](OAc)₂ (M is Mn, Fe, Co, Ni, Cu, and Zn)

The crystal structures of the first-row transition-metal series of tris­(ethyl­enedi­amine-κ²N,N′)metal(II) di­acetate, [M(C₂H₈N₂)₃](CH₃CO₂)₂, with M = Mn, Fe, Co, Ni, Cu, and Zn, are reported. The complexes are all isostructural, crystallizing in a centrosymmetric triclinic cell and possessing an asymmetric unit composed of one [M(en)₃]²⁺ cation and two symmetrically independent acetate anions. In the unit cell, the two complex cations are inversion-generated enanti­omers, possessing the energetically favoured Δ(λλλ) and Λ(δδδ) configurations. The complex cations and acetate anions combine through a series of N—H...O hydrogen bonds to generate a three-dimensional network in the crystals. The other notable feature of the series is a significant Jahn–Teller distortion for the d⁹ Cu²⁺ complex.

Computing details

For all structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: SHELXTL (Sheldrick, 2008) for umd905_a, umd815, umd908, umd943_a, umd886; OLEX2 (Dolomanov et al., 2009) for umd906_a. Software used to prepare material for publication: SHELXTL (Sheldrick, 2008) for umd905_a, umd815, umd908, umd943_a, umd886; OLEX2 (Dolomanov et al., 2009) for umd906_a.

Tris(ethylenediamine-κ²N,N')manganese(II) diacetate (umd905_a)

Crystal data

[Mn(C2H8N2)3](C2H3O2)2	Z = 2
Mr = 353.34	F(000) = 378
Triclinic, P1	Dx = 1.298 Mg m^−3
a = 8.3860 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1422 (9) Å	Cell parameters from 9895 reflections
c = 12.9405 (14) Å	θ = 3.0–25.5°
α = 69.526 (4)°	µ = 0.75 mm^−1
β = 87.160 (4)°	T = 200 K
γ = 76.788 (4)°	Block, colourless
V = 904.33 (16) Å^3	0.28 × 0.20 × 0.18 mm

Data collection

Bruker CMOS diffractometer	3332 independent reflections
Radiation source: fine-focus sealed tube	3047 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.5°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→10
Tmin = 0.817, Tmax = 0.877	k = −11→11
25301 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.060	w = 1/[σ^2(Fo^2) + (0.0254P)^2 + 0.3555P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3332 reflections	Δρmax = 0.29 e Å^−3
229 parameters	Δρmin = −0.18 e Å^−3
12 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (2)

Special details

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. 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 > 2sigma(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
Mn1	0.56819 (2)	0.64374 (2)	0.712668 (16)	0.02420 (9)
O1	0.73843 (14)	0.04560 (14)	0.55454 (10)	0.0425 (3)
O2	0.69158 (18)	0.26521 (16)	0.59452 (14)	0.0689 (5)
N1	0.53719 (16)	0.69532 (15)	0.87081 (10)	0.0308 (3)
H1NB	0.4532 (16)	0.663 (2)	0.9065 (13)	0.037*
H1NA	0.6238 (15)	0.6452 (18)	0.9131 (12)	0.037*
N2	0.44821 (15)	0.90987 (15)	0.65172 (10)	0.0296 (3)
H2NB	0.3727 (16)	0.930 (2)	0.6015 (11)	0.036*
H2NA	0.5213 (17)	0.9641 (18)	0.6213 (13)	0.036*
N3	0.62665 (14)	0.61548 (15)	0.54673 (10)	0.0263 (3)
H3NB	0.639 (2)	0.5156 (12)	0.5547 (13)	0.032*
H3NA	0.5457 (15)	0.6685 (17)	0.4992 (11)	0.032*
N4	0.82619 (15)	0.68812 (15)	0.68501 (10)	0.0299 (3)
H4NB	0.8909 (18)	0.6576 (19)	0.7426 (10)	0.036*
H4NA	0.815 (2)	0.7910 (11)	0.6536 (13)	0.036*
N5	0.62220 (18)	0.37546 (16)	0.80588 (11)	0.0366 (3)
H5NB	0.674 (2)	0.322 (2)	0.7663 (13)	0.044*
H5NA	0.6819 (19)	0.352 (2)	0.8645 (11)	0.044*
N6	0.32040 (16)	0.58508 (18)	0.70418 (11)	0.0375 (3)
H6NB	0.2509 (19)	0.621 (2)	0.7469 (13)	0.045*
H6NA	0.279 (2)	0.632 (2)	0.6373 (9)	0.045*
C1	0.5093 (2)	0.86951 (19)	0.84352 (13)	0.0387 (4)
H1B	0.6134	0.9043	0.8227	0.046*
H1A	0.4680	0.8983	0.9085	0.046*
C2	0.3843 (2)	0.95266 (19)	0.74796 (13)	0.0379 (4)
H2A	0.2797	0.9189	0.7693	0.046*
H2B	0.3631	1.0702	0.7291	0.046*
C3	0.77921 (17)	0.66671 (18)	0.50754 (12)	0.0303 (3)
H3B	0.7556	0.7847	0.4715	0.036*
H3A	0.8273	0.6182	0.4524	0.036*
C4	0.90019 (17)	0.61537 (19)	0.60379 (12)	0.0323 (3)
H4B	0.9272	0.4971	0.6384	0.039*
H4A	1.0027	0.6507	0.5775	0.039*
C5	0.4636 (2)	0.3318 (2)	0.83653 (13)	0.0428 (4)
H5B	0.4195	0.3669	0.8985	0.051*
H5A	0.4787	0.2140	0.8610	0.051*
C6	0.3439 (2)	0.4108 (2)	0.73861 (13)	0.0417 (4)
H6B	0.3869	0.3745	0.6769	0.050*
H6A	0.2376	0.3802	0.7590	0.050*
C7	0.9441 (2)	0.0783 (2)	0.65646 (17)	0.0503 (5)
H7A	0.9695	0.1655	0.6754	0.075*
H7B	1.0283	0.0458	0.6085	0.075*
H7C	0.9417	−0.0133	0.7241	0.075*
C8	0.77878 (17)	0.13513 (16)	0.59685 (11)	0.0275 (3)
O3	0.06899 (15)	0.67463 (17)	0.85093 (10)	0.0515 (3)
O4	0.24077 (13)	0.62274 (15)	0.98985 (9)	0.0437 (3)
C10	−0.0381 (2)	0.7387 (3)	1.00606 (18)	0.0649 (6)
H10A	−0.1340	0.7952	0.9561	0.097*
H10B	−0.0047	0.8131	1.0352	0.097*
H10C	−0.0658	0.6497	1.0673	0.097*
C9	0.10177 (18)	0.67380 (19)	0.94349 (12)	0.0334 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.02426 (13)	0.02828 (13)	0.02108 (12)	−0.00336 (8)	−0.00323 (8)	−0.01091 (9)
O1	0.0480 (7)	0.0409 (6)	0.0435 (7)	−0.0104 (5)	−0.0117 (5)	−0.0189 (5)
O2	0.0623 (9)	0.0453 (8)	0.1023 (12)	0.0180 (6)	−0.0411 (8)	−0.0425 (8)
N1	0.0340 (7)	0.0347 (7)	0.0222 (6)	−0.0018 (5)	−0.0055 (5)	−0.0110 (5)
N2	0.0299 (7)	0.0320 (7)	0.0251 (6)	−0.0027 (5)	−0.0068 (5)	−0.0093 (5)
N3	0.0252 (6)	0.0314 (6)	0.0244 (6)	−0.0039 (5)	−0.0040 (5)	−0.0130 (5)
N4	0.0265 (6)	0.0339 (7)	0.0311 (7)	−0.0040 (5)	−0.0090 (5)	−0.0138 (6)
N5	0.0491 (8)	0.0323 (7)	0.0268 (7)	−0.0036 (6)	−0.0106 (6)	−0.0105 (6)
N6	0.0319 (7)	0.0522 (8)	0.0298 (7)	−0.0128 (6)	−0.0041 (5)	−0.0131 (6)
C1	0.0530 (10)	0.0378 (9)	0.0287 (8)	−0.0067 (7)	−0.0059 (7)	−0.0172 (7)
C2	0.0438 (9)	0.0321 (8)	0.0347 (8)	0.0035 (7)	−0.0037 (7)	−0.0147 (7)
C3	0.0276 (7)	0.0386 (8)	0.0263 (7)	−0.0050 (6)	0.0013 (6)	−0.0150 (6)
C4	0.0219 (7)	0.0389 (8)	0.0363 (8)	−0.0014 (6)	−0.0025 (6)	−0.0163 (7)
C5	0.0677 (12)	0.0402 (9)	0.0258 (8)	−0.0257 (8)	−0.0006 (8)	−0.0092 (7)
C6	0.0491 (10)	0.0574 (11)	0.0319 (8)	−0.0289 (8)	0.0031 (7)	−0.0211 (8)
C7	0.0377 (9)	0.0411 (9)	0.0676 (12)	−0.0101 (7)	−0.0207 (9)	−0.0096 (9)
C8	0.0272 (7)	0.0262 (7)	0.0266 (7)	−0.0073 (6)	−0.0026 (6)	−0.0048 (6)
O3	0.0437 (7)	0.0796 (9)	0.0331 (6)	−0.0129 (6)	−0.0099 (5)	−0.0213 (6)
O4	0.0318 (6)	0.0631 (8)	0.0322 (6)	−0.0055 (5)	−0.0088 (5)	−0.0136 (5)
C10	0.0455 (11)	0.0860 (16)	0.0622 (13)	−0.0029 (10)	0.0068 (10)	−0.0328 (12)
C9	0.0316 (8)	0.0384 (8)	0.0269 (8)	−0.0088 (6)	−0.0037 (6)	−0.0061 (6)

Geometric parameters (Å, º)

Mn1—N1	2.2459 (12)	C1—C2	1.521 (2)
Mn1—N3	2.2680 (12)	C1—H1B	0.9900
Mn1—N5	2.2699 (13)	C1—H1A	0.9900
Mn1—N2	2.2740 (13)	C2—H2A	0.9900
Mn1—N6	2.2784 (13)	C2—H2B	0.9900
Mn1—N4	2.2797 (13)	C3—C4	1.5164 (19)
O1—C8	1.2421 (17)	C3—H3B	0.9900
O2—C8	1.2368 (18)	C3—H3A	0.9900
N1—C1	1.470 (2)	C4—H4B	0.9900
N1—H1NB	0.875 (9)	C4—H4A	0.9900
N1—H1NA	0.866 (9)	C5—C6	1.513 (2)
N2—C2	1.4731 (19)	C5—H5B	0.9900
N2—H2NB	0.872 (9)	C5—H5A	0.9900
N2—H2NA	0.869 (9)	C6—H6B	0.9900
N3—C3	1.4686 (19)	C6—H6A	0.9900
N3—H3NB	0.863 (9)	C7—C8	1.511 (2)
N3—H3NA	0.869 (9)	C7—H7A	0.9800
N4—C4	1.4724 (19)	C7—H7B	0.9800
N4—H4NB	0.868 (9)	C7—H7C	0.9800
N4—H4NA	0.868 (9)	O3—C9	1.2392 (19)
N5—C5	1.472 (2)	O4—C9	1.2495 (18)
N5—H5NB	0.866 (9)	C10—C9	1.519 (2)
N5—H5NA	0.865 (9)	C10—H10A	0.9800
N6—C6	1.464 (2)	C10—H10B	0.9800
N6—H6NB	0.871 (9)	C10—H10C	0.9800
N6—H6NA	0.871 (9)
N1—Mn1—N3	171.45 (5)	C2—C1—H1B	109.9
N1—Mn1—N5	91.55 (5)	N1—C1—H1A	109.9
N3—Mn1—N5	93.58 (5)	C2—C1—H1A	109.9
N1—Mn1—N2	78.00 (5)	H1B—C1—H1A	108.3
N3—Mn1—N2	98.52 (4)	N2—C2—C1	109.23 (12)
N5—Mn1—N2	162.89 (5)	N2—C2—H2A	109.8
N1—Mn1—N6	98.33 (5)	C1—C2—H2A	109.8
N3—Mn1—N6	89.45 (5)	N2—C2—H2B	109.8
N5—Mn1—N6	77.81 (5)	C1—C2—H2B	109.8
N2—Mn1—N6	90.21 (5)	H2A—C2—H2B	108.3
N1—Mn1—N4	94.92 (5)	N3—C3—C4	109.91 (12)
N3—Mn1—N4	77.37 (4)	N3—C3—H3B	109.7
N5—Mn1—N4	101.35 (5)	C4—C3—H3B	109.7
N2—Mn1—N4	93.11 (5)	N3—C3—H3A	109.7
N6—Mn1—N4	166.74 (5)	C4—C3—H3A	109.7
C1—N1—Mn1	108.21 (9)	H3B—C3—H3A	108.2
C1—N1—H1NB	108.8 (11)	N4—C4—C3	108.81 (11)
Mn1—N1—H1NB	111.3 (11)	N4—C4—H4B	109.9
C1—N1—H1NA	111.3 (11)	C3—C4—H4B	109.9
Mn1—N1—H1NA	109.5 (11)	N4—C4—H4A	109.9
H1NB—N1—H1NA	107.8 (16)	C3—C4—H4A	109.9
C2—N2—Mn1	107.94 (9)	H4B—C4—H4A	108.3
C2—N2—H2NB	113.3 (11)	N5—C5—C6	109.89 (13)
Mn1—N2—H2NB	109.1 (11)	N5—C5—H5B	109.7
C2—N2—H2NA	109.1 (11)	C6—C5—H5B	109.7
Mn1—N2—H2NA	109.2 (11)	N5—C5—H5A	109.7
H2NB—N2—H2NA	108.0 (16)	C6—C5—H5A	109.7
C3—N3—Mn1	109.61 (8)	H5B—C5—H5A	108.2
C3—N3—H3NB	109.1 (11)	N6—C6—C5	109.25 (12)
Mn1—N3—H3NB	108.6 (11)	N6—C6—H6B	109.8
C3—N3—H3NA	111.5 (11)	C5—C6—H6B	109.8
Mn1—N3—H3NA	111.0 (11)	N6—C6—H6A	109.8
H3NB—N3—H3NA	106.9 (15)	C5—C6—H6A	109.8
C4—N4—Mn1	107.12 (8)	H6B—C6—H6A	108.3
C4—N4—H4NB	111.1 (11)	C8—C7—H7A	109.5
Mn1—N4—H4NB	117.6 (11)	C8—C7—H7B	109.5
C4—N4—H4NA	106.7 (11)	H7A—C7—H7B	109.5
Mn1—N4—H4NA	106.3 (11)	C8—C7—H7C	109.5
H4NB—N4—H4NA	107.4 (16)	H7A—C7—H7C	109.5
C5—N5—Mn1	107.05 (10)	H7B—C7—H7C	109.5
C5—N5—H5NB	109.9 (12)	O2—C8—O1	124.20 (14)
Mn1—N5—H5NB	111.9 (12)	O2—C8—C7	118.61 (14)
C5—N5—H5NA	110.1 (12)	O1—C8—C7	117.18 (14)
Mn1—N5—H5NA	109.7 (12)	C9—C10—H10A	109.5
H5NB—N5—H5NA	108.1 (17)	C9—C10—H10B	109.5
C6—N6—Mn1	108.52 (10)	H10A—C10—H10B	109.5
C6—N6—H6NB	109.5 (13)	C9—C10—H10C	109.5
Mn1—N6—H6NB	111.4 (12)	H10A—C10—H10C	109.5
C6—N6—H6NA	110.8 (12)	H10B—C10—H10C	109.5
Mn1—N6—H6NA	109.8 (12)	O3—C9—O4	125.15 (15)
H6NB—N6—H6NA	106.8 (17)	O3—C9—C10	117.53 (15)
N1—C1—C2	108.81 (12)	O4—C9—C10	117.32 (15)
N1—C1—H1B	109.9
N3—Mn1—N1—C1	49.3 (3)	N1—Mn1—N5—C5	80.60 (10)
N5—Mn1—N1—C1	176.20 (11)	N3—Mn1—N5—C5	−106.24 (9)
N2—Mn1—N1—C1	−17.47 (10)	N2—Mn1—N5—C5	28.8 (2)
N6—Mn1—N1—C1	−105.90 (11)	N6—Mn1—N5—C5	−17.58 (9)
N4—Mn1—N1—C1	74.67 (10)	N4—Mn1—N5—C5	175.94 (9)
N1—Mn1—N2—C2	−13.44 (10)	N1—Mn1—N6—C6	−102.66 (10)
N3—Mn1—N2—C2	174.51 (10)	N3—Mn1—N6—C6	80.92 (10)
N5—Mn1—N2—C2	40.0 (2)	N5—Mn1—N6—C6	−12.87 (10)
N6—Mn1—N2—C2	85.03 (10)	N2—Mn1—N6—C6	179.44 (10)
N4—Mn1—N2—C2	−107.81 (10)	N4—Mn1—N6—C6	74.9 (2)
N1—Mn1—N3—C3	16.5 (4)	Mn1—N1—C1—C2	45.50 (15)
N5—Mn1—N3—C3	−110.19 (10)	Mn1—N2—C2—C1	41.87 (15)
N2—Mn1—N3—C3	81.93 (9)	N1—C1—C2—N2	−60.16 (17)
N6—Mn1—N3—C3	172.06 (10)	Mn1—N3—C3—C4	38.03 (13)
N4—Mn1—N3—C3	−9.36 (9)	Mn1—N4—C4—C3	47.82 (13)
N1—Mn1—N4—C4	162.87 (9)	N3—C3—C4—N4	−59.09 (16)
N3—Mn1—N4—C4	−20.87 (9)	Mn1—N5—C5—C6	45.71 (15)
N5—Mn1—N4—C4	70.29 (10)	Mn1—N6—C6—C5	41.12 (15)
N2—Mn1—N4—C4	−118.92 (9)	N5—C5—C6—N6	−60.23 (18)
N6—Mn1—N4—C4	−14.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NB···O4	0.88 (1)	2.07 (1)	2.9413 (18)	171 (2)
N1—H1NA···O4^i	0.87 (1)	2.36 (1)	3.0600 (17)	138 (1)
N2—H2NB···O1^ii	0.87 (1)	2.18 (1)	3.0169 (16)	160 (2)
N2—H2NA···O1^iii	0.87 (1)	2.15 (1)	3.0050 (18)	167 (2)
N3—H3NB···O2	0.86 (1)	2.11 (1)	2.9638 (18)	172 (2)
N3—H3NA···O2^ii	0.87 (1)	2.23 (1)	3.0677 (18)	162 (2)
N4—H4NB···O3^iv	0.87 (1)	2.17 (1)	2.9839 (16)	157 (2)
N4—H4NA···O1^iii	0.87 (1)	2.19 (1)	3.0392 (18)	167 (2)
N5—H5NB···O2	0.87 (1)	2.44 (1)	3.215 (2)	149 (2)
N5—H5NA···O4^i	0.87 (1)	2.12 (1)	2.9408 (17)	157 (2)
N6—H6NB···O3	0.87 (1)	2.07 (1)	2.9366 (19)	171 (2)
N6—H6NA···O2^ii	0.87 (1)	2.83 (1)	3.619 (2)	152 (2)

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

Tris(ethylenediamine-κ²N,N')iron(II) diacetate (umd815)

Crystal data

[Fe(C2H8N2)3](C2H3O2)2	Z = 2
Mr = 354.25	F(000) = 380
Triclinic, P1	Dx = 1.320 Mg m^−3
a = 8.3426 (9) Å	Cu Kα radiation, λ = 1.54178 Å
b = 9.1332 (10) Å	Cell parameters from 8016 reflections
c = 12.8165 (14) Å	θ = 6.5–68.4°
α = 70.423 (5)°	µ = 7.00 mm^−1
β = 86.074 (4)°	T = 200 K
γ = 75.628 (5)°	Plate, yellow
V = 891.19 (17) Å^3	0.20 × 0.17 × 0.14 mm

Data collection

Bruker CMOS diffractometer	3214 independent reflections
Radiation source: fine-focus sealed tube	2950 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 68.4°, θmin = 6.5°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→9
Tmin = 0.335, Tmax = 0.441	k = −11→11
11719 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0329P)^2 + 0.4027P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.032
3214 reflections	Δρmax = 0.32 e Å^−3
229 parameters	Δρmin = −0.23 e Å^−3
12 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (8)

Special details

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. 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 > 2sigma(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
Fe1	0.56462 (4)	0.64380 (4)	0.71347 (2)	0.02355 (13)
O1	0.7351 (2)	0.0421 (2)	0.55820 (14)	0.0461 (4)
O2	0.7073 (3)	0.2747 (2)	0.5798 (2)	0.0712 (7)
O3	0.0632 (2)	0.6747 (3)	0.85454 (14)	0.0547 (5)
O4	0.23459 (19)	0.6196 (2)	0.99416 (13)	0.0458 (4)
N1	0.5317 (2)	0.6918 (2)	0.87072 (14)	0.0313 (4)
H1NB	0.449 (2)	0.657 (3)	0.9074 (18)	0.038*
H1NA	0.618 (2)	0.638 (3)	0.9148 (17)	0.038*
N2	0.4475 (2)	0.9036 (2)	0.65327 (14)	0.0312 (4)
H2NB	0.371 (2)	0.923 (3)	0.6046 (16)	0.037*
H2NA	0.522 (2)	0.956 (3)	0.6227 (19)	0.037*
N3	0.6223 (2)	0.6197 (2)	0.54856 (13)	0.0271 (4)
H3NB	0.633 (3)	0.5203 (14)	0.5531 (19)	0.033*
H3NA	0.540 (2)	0.675 (2)	0.5037 (16)	0.033*
N4	0.8175 (2)	0.6856 (2)	0.69066 (15)	0.0316 (4)
H4NB	0.882 (3)	0.653 (3)	0.7488 (14)	0.038*
H4NA	0.806 (3)	0.7891 (13)	0.6636 (19)	0.038*
N5	0.6332 (3)	0.3822 (2)	0.79907 (15)	0.0361 (4)
H5NB	0.688 (3)	0.330 (3)	0.7572 (19)	0.043*
H5NA	0.696 (3)	0.360 (3)	0.8563 (15)	0.043*
N6	0.3246 (2)	0.5854 (3)	0.70608 (15)	0.0377 (4)
H6NB	0.250 (2)	0.621 (3)	0.7476 (19)	0.045*
H6NA	0.284 (3)	0.632 (3)	0.6388 (11)	0.045*
C1	0.5033 (3)	0.8651 (3)	0.84614 (18)	0.0404 (5)
H1B	0.6088	0.8982	0.8261	0.048*
H1A	0.4594	0.8942	0.9121	0.048*
C2	0.3798 (3)	0.9493 (3)	0.75037 (19)	0.0404 (5)
H2A	0.2735	0.9181	0.7713	0.049*
H2B	0.3590	1.0667	0.7322	0.049*
C3	0.7750 (3)	0.6713 (3)	0.50936 (16)	0.0322 (5)
H3B	0.7497	0.7893	0.4763	0.039*
H3A	0.8247	0.6249	0.4516	0.039*
C4	0.8964 (3)	0.6167 (3)	0.60555 (18)	0.0353 (5)
H4B	0.9260	0.4984	0.6368	0.042*
H4A	0.9989	0.6534	0.5799	0.042*
C5	0.4770 (3)	0.3326 (3)	0.83203 (19)	0.0447 (6)
H5B	0.4321	0.3636	0.8971	0.054*
H5A	0.4979	0.2148	0.8530	0.054*
C6	0.3530 (3)	0.4113 (3)	0.73725 (18)	0.0422 (6)
H6B	0.3955	0.3767	0.6731	0.051*
H6A	0.2476	0.3791	0.7599	0.051*
C7	0.9463 (3)	0.0730 (3)	0.6558 (2)	0.0519 (7)
H7A	0.9715	0.1579	0.6779	0.078*
H7B	1.0340	0.0388	0.6081	0.078*
H7C	0.9394	−0.0182	0.7220	0.078*
C8	0.7829 (2)	0.1357 (2)	0.59342 (16)	0.0284 (4)
C9	0.0950 (3)	0.6731 (3)	0.94795 (17)	0.0348 (5)
C10	−0.0470 (4)	0.7411 (5)	1.0117 (3)	0.0682 (9)
H10A	−0.1199	0.6673	1.0370	0.102*
H10B	−0.1097	0.8449	0.9634	0.102*
H10C	−0.0031	0.7550	1.0758	0.102*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.02226 (18)	0.02674 (19)	0.02107 (17)	−0.00375 (12)	−0.00380 (11)	−0.00786 (12)
O1	0.0535 (10)	0.0392 (9)	0.0489 (10)	−0.0160 (8)	−0.0171 (8)	−0.0117 (8)
O2	0.0661 (13)	0.0420 (11)	0.1055 (17)	0.0181 (10)	−0.0449 (12)	−0.0377 (11)
O3	0.0418 (10)	0.0879 (14)	0.0347 (9)	−0.0142 (10)	−0.0100 (7)	−0.0197 (9)
O4	0.0317 (9)	0.0655 (11)	0.0340 (8)	−0.0041 (8)	−0.0104 (7)	−0.0118 (8)
N1	0.0324 (10)	0.0361 (10)	0.0229 (8)	−0.0028 (8)	−0.0052 (7)	−0.0092 (8)
N2	0.0312 (10)	0.0302 (9)	0.0285 (9)	−0.0024 (8)	−0.0098 (7)	−0.0065 (7)
N3	0.0249 (9)	0.0311 (9)	0.0254 (8)	−0.0041 (7)	−0.0046 (7)	−0.0102 (7)
N4	0.0260 (9)	0.0363 (10)	0.0323 (9)	−0.0047 (8)	−0.0090 (7)	−0.0111 (8)
N5	0.0471 (12)	0.0304 (10)	0.0289 (9)	−0.0045 (9)	−0.0112 (8)	−0.0082 (8)
N6	0.0303 (10)	0.0547 (12)	0.0290 (9)	−0.0129 (9)	−0.0009 (8)	−0.0126 (9)
C1	0.0521 (14)	0.0395 (13)	0.0335 (11)	−0.0062 (11)	−0.0066 (10)	−0.0192 (10)
C2	0.0433 (13)	0.0341 (12)	0.0410 (12)	0.0043 (10)	−0.0055 (10)	−0.0171 (10)
C3	0.0298 (11)	0.0406 (12)	0.0265 (10)	−0.0073 (9)	0.0022 (8)	−0.0128 (9)
C4	0.0218 (10)	0.0428 (13)	0.0410 (12)	−0.0032 (9)	−0.0017 (9)	−0.0163 (10)
C5	0.0667 (17)	0.0435 (14)	0.0290 (11)	−0.0269 (13)	−0.0007 (11)	−0.0084 (10)
C6	0.0490 (14)	0.0564 (15)	0.0331 (11)	−0.0288 (12)	0.0017 (10)	−0.0186 (11)
C7	0.0375 (13)	0.0427 (14)	0.0699 (18)	−0.0077 (11)	−0.0226 (12)	−0.0080 (13)
C8	0.0259 (10)	0.0286 (11)	0.0287 (10)	−0.0071 (9)	−0.0008 (8)	−0.0063 (8)
C9	0.0305 (11)	0.0415 (12)	0.0289 (11)	−0.0094 (10)	−0.0039 (9)	−0.0058 (9)
C10	0.0424 (16)	0.095 (2)	0.0633 (18)	−0.0005 (16)	0.0047 (13)	−0.0341 (18)

Geometric parameters (Å, º)

Fe1—N1	2.1880 (17)	N6—H6NB	0.867 (10)
Fe1—N3	2.2062 (16)	N6—H6NA	0.871 (10)
Fe1—N5	2.2115 (19)	C1—C2	1.519 (3)
Fe1—N6	2.2124 (18)	C1—H1B	0.9900
Fe1—N2	2.2147 (18)	C1—H1A	0.9900
Fe1—N4	2.2183 (18)	C2—H2A	0.9900
O1—C8	1.244 (2)	C2—H2B	0.9900
O2—C8	1.228 (3)	C3—C4	1.518 (3)
O3—C9	1.239 (3)	C3—H3B	0.9900
O4—C9	1.250 (3)	C3—H3A	0.9900
N1—C1	1.466 (3)	C4—H4B	0.9900
N1—H1NB	0.871 (10)	C4—H4A	0.9900
N1—H1NA	0.878 (10)	C5—C6	1.510 (4)
N2—C2	1.475 (3)	C5—H5B	0.9900
N2—H2NB	0.871 (10)	C5—H5A	0.9900
N2—H2NA	0.867 (10)	C6—H6B	0.9900
N3—C3	1.466 (3)	C6—H6A	0.9900
N3—H3NB	0.872 (10)	C7—C8	1.510 (3)
N3—H3NA	0.865 (10)	C7—H7A	0.9800
N4—C4	1.475 (3)	C7—H7B	0.9800
N4—H4NB	0.870 (10)	C7—H7C	0.9800
N4—H4NA	0.874 (10)	C9—C10	1.516 (4)
N5—C5	1.474 (3)	C10—H10A	0.9800
N5—H5NB	0.872 (10)	C10—H10B	0.9800
N5—H5NA	0.870 (10)	C10—H10C	0.9800
N6—C6	1.464 (3)
N1—Fe1—N3	171.55 (7)	C2—C1—H1B	110.0
N1—Fe1—N5	91.93 (7)	N1—C1—H1A	110.0
N3—Fe1—N5	93.16 (7)	C2—C1—H1A	110.0
N1—Fe1—N6	98.38 (7)	H1B—C1—H1A	108.4
N3—Fe1—N6	89.16 (6)	N2—C2—C1	109.03 (18)
N5—Fe1—N6	79.85 (8)	N2—C2—H2A	109.9
N1—Fe1—N2	79.84 (7)	C1—C2—H2A	109.9
N3—Fe1—N2	96.26 (7)	N2—C2—H2B	109.9
N5—Fe1—N2	166.99 (7)	C1—C2—H2B	109.9
N6—Fe1—N2	91.31 (7)	H2A—C2—H2B	108.3
N1—Fe1—N4	93.38 (7)	N3—C3—C4	109.66 (17)
N3—Fe1—N4	79.23 (6)	N3—C3—H3B	109.7
N5—Fe1—N4	98.21 (7)	C4—C3—H3B	109.7
N6—Fe1—N4	168.13 (7)	N3—C3—H3A	109.7
N2—Fe1—N4	92.37 (7)	C4—C3—H3A	109.7
C1—N1—Fe1	107.91 (13)	H3B—C3—H3A	108.2
C1—N1—H1NB	110.4 (17)	N4—C4—C3	108.27 (17)
Fe1—N1—H1NB	111.5 (16)	N4—C4—H4B	110.0
C1—N1—H1NA	112.2 (16)	C3—C4—H4B	110.0
Fe1—N1—H1NA	110.7 (16)	N4—C4—H4A	110.0
H1NB—N1—H1NA	104 (2)	C3—C4—H4A	110.0
C2—N2—Fe1	107.38 (13)	H4B—C4—H4A	108.4
C2—N2—H2NB	111.8 (17)	N5—C5—C6	109.93 (18)
Fe1—N2—H2NB	109.3 (17)	N5—C5—H5B	109.7
C2—N2—H2NA	109.4 (16)	C6—C5—H5B	109.7
Fe1—N2—H2NA	109.5 (17)	N5—C5—H5A	109.7
H2NB—N2—H2NA	109 (2)	C6—C5—H5A	109.7
C3—N3—Fe1	109.12 (12)	H5B—C5—H5A	108.2
C3—N3—H3NB	111.0 (16)	N6—C6—C5	109.20 (18)
Fe1—N3—H3NB	109.2 (16)	N6—C6—H6B	109.8
C3—N3—H3NA	112.1 (16)	C5—C6—H6B	109.8
Fe1—N3—H3NA	109.4 (16)	N6—C6—H6A	109.8
H3NB—N3—H3NA	106 (2)	C5—C6—H6A	109.8
C4—N4—Fe1	106.94 (12)	H6B—C6—H6A	108.3
C4—N4—H4NB	110.9 (17)	C8—C7—H7A	109.5
Fe1—N4—H4NB	118.2 (17)	C8—C7—H7B	109.5
C4—N4—H4NA	107.6 (17)	H7A—C7—H7B	109.5
Fe1—N4—H4NA	106.9 (17)	C8—C7—H7C	109.5
H4NB—N4—H4NA	106 (2)	H7A—C7—H7C	109.5
C5—N5—Fe1	106.44 (15)	H7B—C7—H7C	109.5
C5—N5—H5NB	109.6 (17)	O2—C8—O1	124.5 (2)
Fe1—N5—H5NB	112.8 (18)	O2—C8—C7	118.5 (2)
C5—N5—H5NA	111.5 (17)	O1—C8—C7	117.1 (2)
Fe1—N5—H5NA	109.9 (18)	O3—C9—O4	125.4 (2)
H5NB—N5—H5NA	107 (3)	O3—C9—C10	117.3 (2)
C6—N6—Fe1	108.31 (14)	O4—C9—C10	117.3 (2)
C6—N6—H6NB	110.3 (18)	C9—C10—H10A	109.5
Fe1—N6—H6NB	113.6 (17)	C9—C10—H10B	109.5
C6—N6—H6NA	110.4 (18)	H10A—C10—H10B	109.5
Fe1—N6—H6NA	108.9 (18)	C9—C10—H10C	109.5
H6NB—N6—H6NA	105 (3)	H10A—C10—H10C	109.5
N1—C1—C2	108.50 (17)	H10B—C10—H10C	109.5
N1—C1—H1B	110.0
N3—Fe1—N1—C1	45.7 (5)	N1—Fe1—N5—C5	80.71 (14)
N5—Fe1—N1—C1	172.82 (15)	N3—Fe1—N5—C5	−106.03 (13)
N6—Fe1—N1—C1	−107.15 (15)	N6—Fe1—N5—C5	−17.46 (13)
N2—Fe1—N1—C1	−17.32 (14)	N2—Fe1—N5—C5	30.4 (3)
N4—Fe1—N1—C1	74.48 (15)	N4—Fe1—N5—C5	174.41 (13)
N1—Fe1—N2—C2	−13.39 (14)	N1—Fe1—N6—C6	−102.80 (14)
N3—Fe1—N2—C2	174.18 (14)	N3—Fe1—N6—C6	81.04 (14)
N5—Fe1—N2—C2	38.0 (3)	N5—Fe1—N6—C6	−12.32 (13)
N6—Fe1—N2—C2	84.89 (14)	N2—Fe1—N6—C6	177.29 (14)
N4—Fe1—N2—C2	−106.40 (14)	N4—Fe1—N6—C6	69.2 (4)
N1—Fe1—N3—C3	19.4 (5)	Fe1—N1—C1—C2	44.9 (2)
N5—Fe1—N3—C3	−107.63 (14)	Fe1—N2—C2—C1	41.5 (2)
N6—Fe1—N3—C3	172.58 (14)	N1—C1—C2—N2	−59.4 (2)
N2—Fe1—N3—C3	81.36 (14)	Fe1—N3—C3—C4	38.3 (2)
N4—Fe1—N3—C3	−9.87 (14)	Fe1—N4—C4—C3	46.80 (19)
N1—Fe1—N4—C4	163.81 (14)	N3—C3—C4—N4	−58.4 (2)
N3—Fe1—N4—C4	−20.32 (14)	Fe1—N5—C5—C6	44.8 (2)
N5—Fe1—N4—C4	71.36 (14)	Fe1—N6—C6—C5	39.9 (2)
N6—Fe1—N4—C4	−8.3 (4)	N5—C5—C6—N6	−58.7 (3)
N2—Fe1—N4—C4	−116.24 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NB···O4	0.87 (1)	2.08 (1)	2.942 (2)	169 (2)
N1—H1NA···O4^i	0.88 (1)	2.31 (2)	3.050 (3)	142 (2)
N2—H2NB···O1^ii	0.87 (1)	2.21 (1)	3.033 (2)	157 (2)
N2—H2NA···O1^iii	0.87 (1)	2.13 (1)	2.986 (3)	169 (2)
N3—H3NB···O2	0.87 (1)	2.09 (1)	2.945 (3)	168 (2)
N3—H3NA···O2^ii	0.87 (1)	2.26 (1)	3.072 (3)	157 (2)
N4—H4NB···O3^iv	0.87 (1)	2.19 (1)	2.995 (2)	154 (2)
N4—H4NA···O1^iii	0.87 (1)	2.20 (1)	3.050 (3)	163 (2)
N5—H5NB···O2	0.87 (1)	2.47 (2)	3.249 (3)	148 (2)
N5—H5NA···O4^i	0.87 (1)	2.12 (1)	2.933 (2)	156 (2)
N6—H6NB···O3	0.87 (1)	2.08 (1)	2.938 (3)	172 (2)
N6—H6NA···O2^ii	0.87 (1)	2.64 (2)	3.457 (3)	156 (2)

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

Tris(ethylenediamine-κ²N,N')cobalt(II) diacetate (umd906_a)

Crystal data

[Co(C2H8N2)3](C2H3O2)2	Z = 2
Mr = 357.33	F(000) = 382
Triclinic, P1	Dx = 1.347 Mg m^−3
a = 8.3029 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1295 (10) Å	Cell parameters from 9939 reflections
c = 12.7175 (13) Å	θ = 3.0–25.4°
α = 71.021 (4)°	µ = 1.00 mm^−1
β = 85.776 (4)°	T = 200 K
γ = 75.146 (4)°	Plate, pink
V = 881.09 (16) Å^3	0.18 × 0.14 × 0.08 mm

Data collection

Bruker CMOS diffractometer	3228 independent reflections
Radiation source: fine-focus sealed tube	2900 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 25.4°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→10
Tmin = 0.841, Tmax = 0.925	k = −11→11
18117 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.056	w = 1/[σ^2(Fo^2) + (0.0197P)^2 + 0.429P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.008
3228 reflections	Δρmax = 0.25 e Å^−3
229 parameters	Δρmin = −0.21 e Å^−3
12 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0150 (15)

Special details

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. 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 > 2sigma(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
Co1	0.56421 (3)	0.64621 (2)	0.713098 (17)	0.02053 (9)
O1	0.73486 (17)	0.04297 (15)	0.55755 (11)	0.0405 (3)
O2	0.7130 (2)	0.27882 (17)	0.57473 (15)	0.0600 (5)
N1	0.52793 (18)	0.68921 (17)	0.87030 (11)	0.0275 (3)
H1NB	0.4410 (17)	0.659 (2)	0.9046 (14)	0.033*
H1NA	0.6129 (17)	0.6345 (19)	0.9138 (13)	0.033*
N2	0.45016 (18)	0.90141 (17)	0.65411 (12)	0.0268 (3)
H2NB	0.3718 (18)	0.923 (2)	0.6051 (13)	0.032*
H2NA	0.5221 (19)	0.957 (2)	0.6225 (14)	0.032*
N3	0.62086 (17)	0.62139 (16)	0.55011 (11)	0.0226 (3)
H3NB	0.638 (2)	0.5223 (12)	0.5551 (15)	0.027*
H3NA	0.5374 (17)	0.6736 (19)	0.5054 (13)	0.027*
N4	0.81262 (17)	0.68843 (17)	0.69260 (12)	0.0268 (3)
H4NB	0.874 (2)	0.656 (2)	0.7517 (11)	0.032*
H4NA	0.800 (2)	0.7913 (12)	0.6651 (15)	0.032*
N5	0.6378 (2)	0.38943 (17)	0.79340 (12)	0.0304 (3)
H5NB	0.690 (2)	0.340 (2)	0.7486 (14)	0.037*
H5NA	0.702 (2)	0.369 (2)	0.8493 (12)	0.037*
N6	0.32640 (18)	0.59151 (19)	0.70741 (12)	0.0314 (3)
H6NB	0.254 (2)	0.622 (2)	0.7542 (14)	0.038*
H6NA	0.285 (2)	0.639 (2)	0.6404 (10)	0.038*
C1	0.5010 (2)	0.8621 (2)	0.84870 (15)	0.0347 (4)
H1B	0.6081	0.8933	0.8307	0.042*
H1A	0.4548	0.8906	0.9155	0.042*
C2	0.3799 (2)	0.9491 (2)	0.75155 (15)	0.0353 (4)
H2A	0.2714	0.9214	0.7709	0.042*
H2B	0.3615	1.0661	0.7342	0.042*
C3	0.7745 (2)	0.6728 (2)	0.50995 (14)	0.0276 (4)
H3B	0.7485	0.7906	0.4769	0.033*
H3A	0.8254	0.6252	0.4519	0.033*
C4	0.8951 (2)	0.6190 (2)	0.60690 (15)	0.0305 (4)
H4B	0.9259	0.5009	0.6377	0.037*
H4A	0.9979	0.6558	0.5818	0.037*
C5	0.4837 (3)	0.3360 (2)	0.82819 (15)	0.0381 (4)
H5B	0.4400	0.3632	0.8958	0.046*
H5A	0.5073	0.2186	0.8459	0.046*
C6	0.3556 (2)	0.4173 (2)	0.73516 (15)	0.0363 (4)
H6B	0.3964	0.3848	0.6689	0.044*
H6A	0.2502	0.3849	0.7588	0.044*
C7	0.9476 (2)	0.0721 (2)	0.65648 (19)	0.0458 (5)
H7A	0.9746	0.1574	0.6773	0.069*
H7B	1.0367	0.0325	0.6103	0.069*
H7C	0.9369	−0.0156	0.7238	0.069*
C8	0.7854 (2)	0.13658 (19)	0.59199 (13)	0.0246 (3)
O3	0.05832 (17)	0.67811 (19)	0.85660 (11)	0.0479 (4)
O4	0.23078 (15)	0.61838 (17)	0.99746 (10)	0.0402 (3)
C10	−0.0528 (3)	0.7413 (3)	1.0172 (2)	0.0632 (7)
H10A	−0.1248	0.8384	0.9677	0.095*
H10B	−0.0083	0.7670	1.0765	0.095*
H10C	−0.1177	0.6618	1.0500	0.095*
C9	0.0899 (2)	0.6742 (2)	0.95136 (14)	0.0315 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.02004 (13)	0.02428 (13)	0.01723 (12)	−0.00393 (8)	−0.00400 (8)	−0.00682 (8)
O1	0.0486 (8)	0.0350 (7)	0.0414 (8)	−0.0166 (6)	−0.0161 (6)	−0.0084 (6)
O2	0.0594 (10)	0.0357 (8)	0.0842 (12)	0.0139 (7)	−0.0370 (9)	−0.0297 (8)
N1	0.0287 (8)	0.0317 (8)	0.0205 (7)	−0.0035 (6)	−0.0049 (6)	−0.0082 (6)
N2	0.0277 (8)	0.0274 (7)	0.0233 (7)	−0.0025 (6)	−0.0085 (6)	−0.0066 (6)
N3	0.0213 (7)	0.0259 (7)	0.0208 (7)	−0.0038 (6)	−0.0042 (5)	−0.0085 (6)
N4	0.0238 (7)	0.0304 (7)	0.0268 (8)	−0.0055 (6)	−0.0081 (6)	−0.0090 (6)
N5	0.0402 (9)	0.0278 (8)	0.0232 (8)	−0.0057 (6)	−0.0096 (6)	−0.0079 (6)
N6	0.0270 (8)	0.0469 (9)	0.0226 (8)	−0.0125 (7)	−0.0016 (6)	−0.0113 (7)
C1	0.0446 (11)	0.0347 (10)	0.0277 (9)	−0.0050 (8)	−0.0059 (8)	−0.0160 (8)
C2	0.0375 (10)	0.0315 (9)	0.0334 (10)	0.0040 (8)	−0.0057 (8)	−0.0141 (8)
C3	0.0251 (9)	0.0340 (9)	0.0248 (9)	−0.0076 (7)	0.0022 (7)	−0.0110 (7)
C4	0.0202 (8)	0.0371 (9)	0.0345 (10)	−0.0041 (7)	−0.0020 (7)	−0.0134 (8)
C5	0.0592 (13)	0.0370 (10)	0.0230 (9)	−0.0255 (9)	−0.0009 (8)	−0.0055 (8)
C6	0.0443 (11)	0.0498 (11)	0.0265 (9)	−0.0273 (9)	0.0029 (8)	−0.0164 (8)
C7	0.0370 (11)	0.0374 (11)	0.0596 (14)	−0.0077 (8)	−0.0218 (10)	−0.0072 (10)
C8	0.0228 (8)	0.0268 (9)	0.0234 (8)	−0.0072 (7)	−0.0012 (6)	−0.0059 (7)
O3	0.0361 (8)	0.0806 (11)	0.0283 (7)	−0.0124 (7)	−0.0087 (6)	−0.0184 (7)
O4	0.0287 (7)	0.0599 (9)	0.0282 (7)	−0.0073 (6)	−0.0084 (5)	−0.0099 (6)
C10	0.0403 (13)	0.0936 (19)	0.0538 (14)	−0.0018 (12)	0.0042 (11)	−0.0329 (14)
C9	0.0274 (9)	0.0389 (10)	0.0254 (9)	−0.0093 (7)	−0.0032 (7)	−0.0050 (7)

Geometric parameters (Å, º)

Co1—N1	2.1455 (14)	C1—H1B	0.9900
Co1—N2	2.1735 (14)	C1—H1A	0.9900
Co1—N3	2.1625 (13)	C1—C2	1.518 (2)
Co1—N4	2.1757 (14)	C2—H2A	0.9900
Co1—N5	2.1708 (15)	C2—H2B	0.9900
Co1—N6	2.1687 (15)	C3—H3B	0.9900
O1—C8	1.2460 (19)	C3—H3A	0.9900
O2—C8	1.237 (2)	C3—C4	1.517 (2)
N1—H1NB	0.874 (9)	C4—H4B	0.9900
N1—H1NA	0.866 (9)	C4—H4A	0.9900
N1—C1	1.471 (2)	C5—H5B	0.9900
N2—H2NB	0.874 (9)	C5—H5A	0.9900
N2—H2NA	0.871 (9)	C5—C6	1.514 (3)
N2—C2	1.476 (2)	C6—H6B	0.9900
N3—H3NB	0.861 (9)	C6—H6A	0.9900
N3—H3NA	0.862 (9)	C7—H7A	0.9800
N3—C3	1.471 (2)	C7—H7B	0.9800
N4—H4NB	0.864 (9)	C7—H7C	0.9800
N4—H4NA	0.870 (9)	C7—C8	1.508 (2)
N4—C4	1.475 (2)	O3—C9	1.239 (2)
N5—H5NB	0.863 (9)	O4—C9	1.254 (2)
N5—H5NA	0.865 (9)	C10—H10A	0.9800
N5—C5	1.472 (2)	C10—H10B	0.9800
N6—H6NB	0.875 (9)	C10—H10C	0.9800
N6—H6NA	0.870 (9)	C10—C9	1.515 (3)
N6—C6	1.471 (2)
N1—Co1—N2	81.10 (5)	N1—C1—C2	108.29 (14)
N1—Co1—N3	173.17 (5)	H1B—C1—H1A	108.4
N1—Co1—N4	93.52 (6)	C2—C1—H1B	110.0
N1—Co1—N5	91.80 (6)	C2—C1—H1A	110.0
N1—Co1—N6	96.53 (6)	N2—C2—C1	108.83 (14)
N2—Co1—N4	91.32 (6)	N2—C2—H2A	109.9
N3—Co1—N2	95.85 (5)	N2—C2—H2B	109.9
N3—Co1—N4	80.39 (5)	C1—C2—H2A	109.9
N3—Co1—N5	92.06 (5)	C1—C2—H2B	109.9
N3—Co1—N6	89.64 (5)	H2A—C2—H2B	108.3
N5—Co1—N2	169.01 (6)	N3—C3—H3B	109.9
N5—Co1—N4	97.53 (6)	N3—C3—H3A	109.9
N6—Co1—N2	91.42 (6)	N3—C3—C4	108.98 (13)
N6—Co1—N4	169.88 (5)	H3B—C3—H3A	108.3
N6—Co1—N5	81.00 (6)	C4—C3—H3B	109.9
Co1—N1—H1NB	111.6 (13)	C4—C3—H3A	109.9
Co1—N1—H1NA	110.3 (13)	N4—C4—C3	108.07 (13)
H1NB—N1—H1NA	106.5 (18)	N4—C4—H4B	110.1
C1—N1—Co1	107.67 (10)	N4—C4—H4A	110.1
C1—N1—H1NB	108.8 (12)	C3—C4—H4B	110.1
C1—N1—H1NA	112.1 (12)	C3—C4—H4A	110.1
Co1—N2—H2NB	110.6 (12)	H4B—C4—H4A	108.4
Co1—N2—H2NA	112.0 (13)	N5—C5—H5B	109.8
H2NB—N2—H2NA	107.4 (18)	N5—C5—H5A	109.8
C2—N2—Co1	107.44 (10)	N5—C5—C6	109.29 (14)
C2—N2—H2NB	110.4 (13)	H5B—C5—H5A	108.3
C2—N2—H2NA	109.0 (12)	C6—C5—H5B	109.8
Co1—N3—H3NB	109.1 (12)	C6—C5—H5A	109.8
Co1—N3—H3NA	110.4 (12)	N6—C6—C5	109.08 (14)
H3NB—N3—H3NA	107.3 (17)	N6—C6—H6B	109.9
C3—N3—Co1	109.16 (9)	N6—C6—H6A	109.9
C3—N3—H3NB	108.0 (12)	C5—C6—H6B	109.9
C3—N3—H3NA	112.8 (12)	C5—C6—H6A	109.9
Co1—N4—H4NB	117.2 (13)	H6B—C6—H6A	108.3
Co1—N4—H4NA	106.7 (13)	H7A—C7—H7B	109.5
H4NB—N4—H4NA	107.2 (17)	H7A—C7—H7C	109.5
C4—N4—Co1	106.73 (10)	H7B—C7—H7C	109.5
C4—N4—H4NB	111.5 (13)	C8—C7—H7A	109.5
C4—N4—H4NA	107.0 (13)	C8—C7—H7B	109.5
Co1—N5—H5NB	111.9 (13)	C8—C7—H7C	109.5
Co1—N5—H5NA	108.7 (13)	O1—C8—C7	117.42 (15)
H5NB—N5—H5NA	109.1 (19)	O2—C8—O1	124.27 (16)
C5—N5—Co1	106.95 (11)	O2—C8—C7	118.30 (15)
C5—N5—H5NB	108.2 (13)	H10A—C10—H10B	109.5
C5—N5—H5NA	112.0 (13)	H10A—C10—H10C	109.5
Co1—N6—H6NB	113.5 (13)	H10B—C10—H10C	109.5
Co1—N6—H6NA	108.5 (13)	C9—C10—H10A	109.5
H6NB—N6—H6NA	108.8 (19)	C9—C10—H10B	109.5
C6—N6—Co1	108.10 (11)	C9—C10—H10C	109.5
C6—N6—H6NB	108.1 (13)	O3—C9—O4	125.14 (17)
C6—N6—H6NA	109.9 (13)	O3—C9—C10	117.61 (17)
N1—C1—H1B	110.0	O4—C9—C10	117.25 (17)
N1—C1—H1A	110.0
Co1—N1—C1—C2	44.81 (16)	N3—Co1—N5—C5	−106.27 (11)
Co1—N2—C2—C1	40.46 (17)	N3—Co1—N6—C6	79.47 (11)
Co1—N3—C3—C4	37.93 (15)	N3—C3—C4—N4	−57.83 (17)
Co1—N4—C4—C3	46.87 (15)	N4—Co1—N1—C1	73.08 (12)
Co1—N5—C5—C6	43.75 (16)	N4—Co1—N2—C2	−106.02 (11)
Co1—N6—C6—C5	39.93 (16)	N4—Co1—N3—C3	−9.67 (10)
N1—Co1—N2—C2	−12.67 (11)	N4—Co1—N5—C5	173.15 (11)
N1—Co1—N3—C3	17.5 (5)	N4—Co1—N6—C6	69.7 (4)
N1—Co1—N4—C4	162.61 (11)	N5—Co1—N1—C1	170.74 (11)
N1—Co1—N5—C5	79.36 (11)	N5—Co1—N2—C2	37.6 (3)
N1—Co1—N6—C6	−103.48 (11)	N5—Co1—N3—C3	−106.96 (11)
N1—C1—C2—N2	−58.3 (2)	N5—Co1—N4—C4	70.32 (11)
N2—Co1—N1—C1	−17.70 (11)	N5—Co1—N6—C6	−12.68 (11)
N2—Co1—N3—C3	80.67 (11)	N5—C5—C6—N6	−57.53 (19)
N2—Co1—N4—C4	−116.23 (11)	N6—Co1—N1—C1	−108.12 (12)
N2—Co1—N5—C5	29.8 (3)	N6—Co1—N2—C2	83.72 (11)
N2—Co1—N6—C6	175.31 (11)	N6—Co1—N3—C3	172.06 (11)
N3—Co1—N1—C1	46.3 (5)	N6—Co1—N4—C4	−10.6 (4)
N3—Co1—N2—C2	173.50 (11)	N6—Co1—N5—C5	−16.96 (11)
N3—Co1—N4—C4	−20.51 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NB···O4	0.87 (1)	2.08 (1)	2.945 (2)	170 (2)
N1—H1NA···O4^i	0.87 (1)	2.30 (1)	3.0443 (19)	145 (2)
N2—H2NB···O1^ii	0.87 (1)	2.21 (1)	3.0305 (18)	157 (2)
N2—H2NA···O1^iii	0.87 (1)	2.12 (1)	2.979 (2)	168 (2)
N3—H3NB···O2	0.86 (1)	2.08 (1)	2.9387 (19)	172 (2)
N3—H3NA···O2^ii	0.86 (1)	2.26 (1)	3.074 (2)	157 (2)
N4—H4NB···O3^iv	0.86 (1)	2.19 (1)	2.9868 (18)	153 (2)
N4—H4NA···O1^iii	0.87 (1)	2.21 (1)	3.053 (2)	164 (2)
N5—H5NB···O2	0.86 (1)	2.44 (1)	3.223 (2)	152 (2)
N5—H5NA···O4^i	0.87 (1)	2.11 (1)	2.9215 (19)	156 (2)
N6—H6NB···O3	0.88 (1)	2.07 (1)	2.938 (2)	171 (2)
N6—H6NA···O2^ii	0.87 (1)	2.59 (1)	3.405 (2)	156 (2)

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

Tris(ethylenediamine-κ²N,N')nickel(II) diacetate (umd908)

Crystal data

[Ni(C2H8N2)3](C2H3O2)2	Z = 2
Mr = 357.11	F(000) = 384
Triclinic, P1	Dx = 1.367 Mg m^−3
a = 8.2974 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0619 (11) Å	Cell parameters from 9139 reflections
c = 12.5998 (17) Å	θ = 3.1–25.4°
α = 71.960 (4)°	µ = 1.14 mm^−1
β = 85.204 (5)°	T = 200 K
γ = 74.321 (4)°	Block, green
V = 867.29 (19) Å^3	0.21 × 0.17 × 0.12 mm

Data collection

Bruker CMOS diffractometer	3175 independent reflections
Radiation source: fine-focus sealed tube	3010 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 25.4°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→10
Tmin = 0.796, Tmax = 0.875	k = −10→10
25372 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.019	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.049	w = 1/[σ^2(Fo^2) + (0.0185P)^2 + 0.4044P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.015
3175 reflections	Δρmax = 0.27 e Å^−3
229 parameters	Δρmin = −0.23 e Å^−3
12 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (2)

Special details

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. 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 > 2sigma(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
Ni1	0.56174 (2)	0.647713 (19)	0.713433 (13)	0.01785 (8)
O1	0.72555 (16)	0.04539 (14)	0.56195 (10)	0.0416 (3)
O2	0.72642 (17)	0.28635 (14)	0.56539 (12)	0.0507 (3)
N1	0.52299 (15)	0.68764 (15)	0.87080 (10)	0.0248 (3)
H1NB	0.4349 (15)	0.6596 (19)	0.9054 (13)	0.030*
H1NA	0.6106 (15)	0.6347 (18)	0.9116 (12)	0.030*
N2	0.44608 (15)	0.89785 (14)	0.65675 (10)	0.0248 (3)
H2NB	0.3713 (17)	0.9171 (19)	0.6067 (11)	0.030*
H2NA	0.5188 (17)	0.9520 (18)	0.6269 (13)	0.030*
N3	0.61690 (14)	0.62791 (14)	0.55076 (9)	0.0207 (2)
H3NB	0.6337 (19)	0.5296 (12)	0.5532 (13)	0.025*
H3NA	0.5344 (15)	0.6849 (17)	0.5061 (11)	0.025*
N4	0.80561 (15)	0.68763 (15)	0.69738 (10)	0.0253 (3)
H4NB	0.8677 (18)	0.6519 (19)	0.7564 (10)	0.030*
H4NA	0.794 (2)	0.7903 (11)	0.6737 (14)	0.030*
N5	0.64437 (16)	0.39612 (14)	0.78853 (10)	0.0272 (3)
H5NB	0.7007 (19)	0.3480 (19)	0.7423 (12)	0.033*
H5NA	0.7071 (19)	0.378 (2)	0.8447 (11)	0.033*
N6	0.32979 (16)	0.59221 (16)	0.70824 (10)	0.0278 (3)
H6NB	0.2551 (18)	0.624 (2)	0.7544 (12)	0.033*
H6NA	0.288 (2)	0.6388 (19)	0.6413 (9)	0.033*
C1	0.4927 (2)	0.86129 (18)	0.85209 (13)	0.0326 (3)
H1B	0.5993	0.8932	0.8347	0.039*
H1A	0.4441	0.8895	0.9199	0.039*
C2	0.3721 (2)	0.94759 (18)	0.75489 (13)	0.0334 (3)
H2A	0.2637	0.9198	0.7739	0.040*
H2B	0.3520	1.0653	0.7383	0.040*
C3	0.77221 (17)	0.67664 (18)	0.51149 (12)	0.0262 (3)
H3B	0.7471	0.7950	0.4800	0.031*
H3A	0.8240	0.6285	0.4522	0.031*
C4	0.89155 (17)	0.61997 (19)	0.60919 (13)	0.0290 (3)
H4B	0.9234	0.5012	0.6374	0.035*
H4A	0.9945	0.6569	0.5855	0.035*
C5	0.4936 (2)	0.33721 (19)	0.82477 (13)	0.0349 (4)
H5B	0.4493	0.3625	0.8943	0.042*
H5A	0.5222	0.2192	0.8401	0.042*
C6	0.3629 (2)	0.4170 (2)	0.73365 (12)	0.0328 (3)
H6B	0.4036	0.3848	0.6659	0.039*
H6A	0.2586	0.3832	0.7586	0.039*
C7	0.9475 (2)	0.0684 (2)	0.65631 (17)	0.0456 (4)
H7A	0.9777	0.1525	0.6778	0.068*
H7B	1.0369	0.0238	0.6103	0.068*
H7C	0.9325	−0.0171	0.7235	0.068*
C8	0.78614 (17)	0.13917 (16)	0.59041 (11)	0.0226 (3)
O3	0.05512 (15)	0.68032 (17)	0.85836 (9)	0.0458 (3)
O4	0.22577 (13)	0.61536 (15)	1.00070 (9)	0.0379 (3)
C10	−0.0593 (2)	0.7434 (3)	1.02143 (18)	0.0610 (6)
H10A	−0.1259	0.8460	0.9740	0.092*
H10B	−0.0157	0.7606	1.0853	0.092*
H10C	−0.1298	0.6682	1.0483	0.092*
C9	0.08530 (18)	0.67426 (19)	0.95450 (12)	0.0294 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.01869 (11)	0.02042 (11)	0.01467 (10)	−0.00450 (7)	−0.00408 (6)	−0.00497 (7)
O1	0.0522 (7)	0.0365 (6)	0.0409 (7)	−0.0230 (5)	−0.0179 (6)	−0.0040 (5)
O2	0.0534 (8)	0.0296 (6)	0.0662 (9)	0.0089 (5)	−0.0279 (7)	−0.0202 (6)
N1	0.0255 (6)	0.0287 (6)	0.0191 (6)	−0.0035 (5)	−0.0054 (5)	−0.0074 (5)
N2	0.0254 (6)	0.0243 (6)	0.0228 (6)	−0.0038 (5)	−0.0080 (5)	−0.0048 (5)
N3	0.0204 (6)	0.0234 (6)	0.0184 (6)	−0.0046 (5)	−0.0039 (4)	−0.0063 (5)
N4	0.0229 (6)	0.0281 (6)	0.0262 (6)	−0.0069 (5)	−0.0087 (5)	−0.0075 (5)
N5	0.0365 (7)	0.0248 (6)	0.0201 (6)	−0.0058 (5)	−0.0081 (5)	−0.0062 (5)
N6	0.0254 (6)	0.0413 (7)	0.0199 (6)	−0.0133 (5)	−0.0013 (5)	−0.0090 (5)
C1	0.0413 (9)	0.0322 (8)	0.0274 (8)	−0.0051 (7)	−0.0061 (7)	−0.0154 (6)
C2	0.0373 (9)	0.0275 (8)	0.0325 (8)	0.0029 (6)	−0.0066 (7)	−0.0129 (6)
C3	0.0252 (7)	0.0313 (8)	0.0226 (7)	−0.0085 (6)	0.0026 (6)	−0.0081 (6)
C4	0.0181 (7)	0.0358 (8)	0.0331 (8)	−0.0057 (6)	−0.0012 (6)	−0.0112 (6)
C5	0.0554 (10)	0.0317 (8)	0.0222 (7)	−0.0229 (7)	−0.0020 (7)	−0.0040 (6)
C6	0.0412 (9)	0.0444 (9)	0.0236 (7)	−0.0263 (7)	0.0025 (6)	−0.0129 (7)
C7	0.0362 (9)	0.0374 (9)	0.0599 (12)	−0.0089 (7)	−0.0232 (8)	−0.0044 (8)
C8	0.0218 (7)	0.0256 (7)	0.0203 (7)	−0.0081 (6)	−0.0004 (5)	−0.0051 (5)
O3	0.0338 (6)	0.0786 (9)	0.0252 (6)	−0.0134 (6)	−0.0072 (5)	−0.0150 (6)
O4	0.0278 (6)	0.0548 (7)	0.0274 (6)	−0.0076 (5)	−0.0086 (5)	−0.0077 (5)
C10	0.0390 (11)	0.0916 (17)	0.0505 (12)	−0.0032 (10)	0.0058 (9)	−0.0319 (12)
C9	0.0263 (7)	0.0376 (8)	0.0226 (7)	−0.0100 (6)	−0.0022 (6)	−0.0047 (6)

Geometric parameters (Å, º)

Ni1—N1	2.1073 (12)	C1—C2	1.517 (2)
Ni1—N3	2.1140 (12)	C1—H1B	0.9900
Ni1—N5	2.1192 (12)	C1—H1A	0.9900
Ni1—N2	2.1225 (12)	C2—H2A	0.9900
Ni1—N6	2.1274 (12)	C2—H2B	0.9900
Ni1—N4	2.1326 (12)	C3—C4	1.516 (2)
O1—C8	1.2464 (17)	C3—H3B	0.9900
O2—C8	1.2378 (18)	C3—H3A	0.9900
N1—C1	1.4702 (19)	C4—H4B	0.9900
N1—H1NB	0.876 (9)	C4—H4A	0.9900
N1—H1NA	0.862 (9)	C5—C6	1.513 (2)
N2—C2	1.4757 (19)	C5—H5B	0.9900
N2—H2NB	0.867 (9)	C5—H5A	0.9900
N2—H2NA	0.869 (9)	C6—H6B	0.9900
N3—C3	1.4718 (18)	C6—H6A	0.9900
N3—H3NB	0.855 (9)	C7—C8	1.512 (2)
N3—H3NA	0.863 (9)	C7—H7A	0.9800
N4—C4	1.4739 (19)	C7—H7B	0.9800
N4—H4NB	0.865 (9)	C7—H7C	0.9800
N4—H4NA	0.865 (9)	O3—C9	1.2389 (19)
N5—C5	1.474 (2)	O4—C9	1.2518 (18)
N5—H5NB	0.866 (9)	C10—C9	1.515 (2)
N5—H5NA	0.861 (9)	C10—H10A	0.9800
N6—C6	1.471 (2)	C10—H10B	0.9800
N6—H6NB	0.869 (9)	C10—H10C	0.9800
N6—H6NA	0.870 (9)
N1—Ni1—N3	173.32 (5)	C2—C1—H1B	110.1
N1—Ni1—N5	91.41 (5)	N1—C1—H1A	110.1
N3—Ni1—N5	92.79 (5)	C2—C1—H1A	110.1
N1—Ni1—N2	82.37 (5)	H1B—C1—H1A	108.5
N3—Ni1—N2	94.05 (5)	N2—C2—C1	108.53 (12)
N5—Ni1—N2	170.69 (5)	N2—C2—H2A	110.0
N1—Ni1—N6	96.03 (5)	C1—C2—H2A	110.0
N3—Ni1—N6	89.68 (5)	N2—C2—H2B	110.0
N5—Ni1—N6	82.34 (5)	C1—C2—H2B	110.0
N2—Ni1—N6	91.39 (5)	H2A—C2—H2B	108.4
N1—Ni1—N4	92.73 (5)	N3—C3—C4	108.78 (11)
N3—Ni1—N4	81.72 (5)	N3—C3—H3B	109.9
N5—Ni1—N4	95.22 (5)	C4—C3—H3B	109.9
N2—Ni1—N4	92.01 (5)	N3—C3—H3A	109.9
N6—Ni1—N4	170.96 (5)	C4—C3—H3A	109.9
C1—N1—Ni1	107.39 (9)	H3B—C3—H3A	108.3
C1—N1—H1NB	107.0 (11)	N4—C4—C3	107.87 (11)
Ni1—N1—H1NB	112.9 (11)	N4—C4—H4B	110.1
C1—N1—H1NA	111.1 (11)	C3—C4—H4B	110.1
Ni1—N1—H1NA	109.1 (11)	N4—C4—H4A	110.1
H1NB—N1—H1NA	109.4 (16)	C3—C4—H4A	110.1
C2—N2—Ni1	107.47 (9)	H4B—C4—H4A	108.4
C2—N2—H2NB	111.9 (11)	N5—C5—C6	109.10 (12)
Ni1—N2—H2NB	109.8 (11)	N5—C5—H5B	109.9
C2—N2—H2NA	108.5 (11)	C6—C5—H5B	109.9
Ni1—N2—H2NA	111.2 (11)	N5—C5—H5A	109.9
H2NB—N2—H2NA	108.1 (16)	C6—C5—H5A	109.9
C3—N3—Ni1	109.22 (8)	H5B—C5—H5A	108.3
C3—N3—H3NB	107.8 (11)	N6—C6—C5	108.70 (12)
Ni1—N3—H3NB	108.9 (11)	N6—C6—H6B	109.9
C3—N3—H3NA	111.5 (11)	C5—C6—H6B	109.9
Ni1—N3—H3NA	110.6 (11)	N6—C6—H6A	109.9
H3NB—N3—H3NA	108.7 (15)	C5—C6—H6A	109.9
C4—N4—Ni1	106.53 (8)	H6B—C6—H6A	108.3
C4—N4—H4NB	110.3 (11)	C8—C7—H7A	109.5
Ni1—N4—H4NB	118.1 (11)	C8—C7—H7B	109.5
C4—N4—H4NA	107.5 (11)	H7A—C7—H7B	109.5
Ni1—N4—H4NA	107.9 (11)	C8—C7—H7C	109.5
H4NB—N4—H4NA	106.1 (16)	H7A—C7—H7C	109.5
C5—N5—Ni1	106.97 (10)	H7B—C7—H7C	109.5
C5—N5—H5NB	109.4 (12)	O2—C8—O1	124.58 (14)
Ni1—N5—H5NB	111.8 (12)	O2—C8—C7	117.93 (13)
C5—N5—H5NA	110.8 (12)	O1—C8—C7	117.44 (13)
Ni1—N5—H5NA	108.9 (11)	C9—C10—H10A	109.5
H5NB—N5—H5NA	108.9 (16)	C9—C10—H10B	109.5
C6—N6—Ni1	108.00 (9)	H10A—C10—H10B	109.5
C6—N6—H6NB	109.2 (12)	C9—C10—H10C	109.5
Ni1—N6—H6NB	114.1 (12)	H10A—C10—H10C	109.5
C6—N6—H6NA	109.5 (11)	H10B—C10—H10C	109.5
Ni1—N6—H6NA	108.7 (12)	O3—C9—O4	125.16 (15)
H6NB—N6—H6NA	107.3 (16)	O3—C9—C10	117.39 (15)
N1—C1—C2	107.84 (12)	O4—C9—C10	117.45 (15)
N1—C1—H1B	110.1
N3—Ni1—N1—C1	40.2 (4)	N1—Ni1—N5—C5	79.04 (9)
N5—Ni1—N1—C1	169.19 (10)	N3—Ni1—N5—C5	−106.16 (9)
N2—Ni1—N1—C1	−17.76 (10)	N2—Ni1—N5—C5	31.2 (3)
N6—Ni1—N1—C1	−108.36 (10)	N6—Ni1—N5—C5	−16.85 (9)
N4—Ni1—N1—C1	73.90 (10)	N4—Ni1—N5—C5	171.91 (9)
N1—Ni1—N2—C2	−12.57 (10)	N1—Ni1—N6—C6	−103.11 (9)
N3—Ni1—N2—C2	173.11 (10)	N3—Ni1—N6—C6	80.37 (9)
N5—Ni1—N2—C2	35.9 (3)	N5—Ni1—N6—C6	−12.49 (9)
N6—Ni1—N2—C2	83.32 (10)	N2—Ni1—N6—C6	174.41 (9)
N4—Ni1—N2—C2	−105.06 (10)	N4—Ni1—N6—C6	62.4 (3)
N1—Ni1—N3—C3	25.1 (4)	Ni1—N1—C1—C2	44.48 (14)
N5—Ni1—N3—C3	−103.79 (9)	Ni1—N2—C2—C1	40.20 (14)
N2—Ni1—N3—C3	82.52 (9)	N1—C1—C2—N2	−57.66 (17)
N6—Ni1—N3—C3	173.89 (9)	Ni1—N3—C3—C4	36.79 (13)
N4—Ni1—N3—C3	−8.92 (9)	Ni1—N4—C4—C3	46.53 (13)
N1—Ni1—N4—C4	162.87 (9)	N3—C3—C4—N4	−56.57 (15)
N3—Ni1—N4—C4	−20.87 (9)	Ni1—N5—C5—C6	43.22 (14)
N5—Ni1—N4—C4	71.20 (9)	Ni1—N6—C6—C5	39.26 (14)
N2—Ni1—N4—C4	−114.67 (9)	N5—C5—C6—N6	−56.38 (17)
N6—Ni1—N4—C4	−2.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NA···O4^i	0.86 (1)	2.29 (1)	3.0370 (17)	145 (1)
N1—H1NB···O4	0.88 (1)	2.08 (1)	2.9536 (17)	172 (2)
N2—H2NA···O1^ii	0.87 (1)	2.11 (1)	2.9690 (18)	170 (2)
N2—H2NB···O1^iii	0.87 (1)	2.23 (1)	3.0444 (17)	157 (2)
N3—H3NA···O2^iii	0.86 (1)	2.33 (1)	3.1076 (17)	150 (1)
N3—H3NB···O2	0.86 (1)	2.09 (1)	2.9316 (17)	168 (2)
N4—H4NA···O1^ii	0.87 (1)	2.25 (1)	3.0762 (17)	160 (2)
N4—H4NB···O3^iv	0.87 (1)	2.21 (1)	2.9916 (16)	150 (2)
N5—H5NA···O4^i	0.86 (1)	2.09 (1)	2.9105 (17)	158 (2)
N5—H5NB···O2	0.87 (1)	2.44 (1)	3.2254 (19)	151 (2)
N6—H6NA···O2^iii	0.87 (1)	2.48 (1)	3.3102 (19)	159 (2)
N6—H6NB···O3	0.87 (1)	2.08 (1)	2.9395 (18)	171 (2)

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

Tris(ethylenediamine-κ²N,N')copper(II) diacetate (umd943_a)

Crystal data

[Cu(C2H8N2)3](C2H3O2)2	Z = 2
Mr = 361.94	F(000) = 386
Triclinic, P1	Dx = 1.396 Mg m^−3
a = 8.2953 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9144 (8) Å	Cell parameters from 9890 reflections
c = 12.7148 (12) Å	θ = 3.1–25.7°
α = 75.244 (4)°	µ = 1.29 mm^−1
β = 85.082 (4)°	T = 200 K
γ = 71.226 (4)°	Block, blue
V = 860.84 (14) Å^3	0.20 × 0.15 × 0.10 mm

Data collection

Bruker CMOS diffractometer	3287 independent reflections
Radiation source: fine-focus sealed tube	2965 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 25.8°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→10
Tmin = 0.782, Tmax = 0.882	k = −10→10
30526 measured reflections	l = −15→15

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0374P)^2 + 0.3532P] where P = (Fo^2 + 2Fc^2)/3
3287 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.51 e Å^−3
12 restraints	Δρmin = −0.28 e Å^−3

Special details

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. 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 > 2sigma(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
Cu1	0.56204 (2)	0.64182 (2)	0.718635 (15)	0.02012 (8)
O1	0.6820 (2)	0.0576 (2)	0.58732 (16)	0.0601 (5)
O2	0.74119 (19)	0.28624 (16)	0.52924 (12)	0.0410 (3)
N1	0.51464 (19)	0.68440 (18)	0.87074 (12)	0.0236 (3)
H1NB	0.4303 (19)	0.653 (2)	0.9026 (15)	0.028*
H1NA	0.6045 (18)	0.631 (2)	0.9099 (14)	0.028*
N2	0.4010 (2)	0.9224 (2)	0.67347 (14)	0.0330 (4)
H2NB	0.321 (2)	0.947 (3)	0.6269 (15)	0.040*
H2NA	0.467 (2)	0.979 (2)	0.6437 (17)	0.040*
N3	0.61954 (19)	0.61788 (19)	0.56330 (12)	0.0240 (3)
H3NB	0.643 (3)	0.5170 (13)	0.5615 (17)	0.029*
H3NA	0.5324 (19)	0.675 (2)	0.5235 (14)	0.029*
N4	0.7888 (2)	0.6957 (2)	0.70599 (13)	0.0290 (3)
H4NB	0.850 (2)	0.667 (3)	0.7638 (12)	0.035*
H4NA	0.763 (3)	0.8004 (12)	0.6837 (17)	0.035*
N5	0.6611 (2)	0.3534 (2)	0.80270 (14)	0.0360 (4)
H5NB	0.727 (3)	0.293 (2)	0.7626 (16)	0.043*
H5NA	0.714 (3)	0.339 (3)	0.8623 (12)	0.043*
N6	0.3432 (2)	0.57903 (19)	0.71268 (12)	0.0266 (3)
H6NB	0.264 (2)	0.616 (2)	0.7571 (14)	0.032*
H6NA	0.296 (3)	0.625 (2)	0.6498 (11)	0.032*
C1	0.4703 (3)	0.8600 (2)	0.86476 (16)	0.0336 (4)
H1B	0.5728	0.8956	0.8461	0.040*
H1A	0.4271	0.8817	0.9362	0.040*
C2	0.3349 (3)	0.9538 (2)	0.77858 (18)	0.0358 (5)
H2A	0.2319	0.9192	0.7978	0.043*
H2B	0.3028	1.0722	0.7745	0.043*
C3	0.7694 (2)	0.6710 (3)	0.52449 (15)	0.0326 (4)
H3B	0.7337	0.7907	0.4945	0.039*
H3A	0.8280	0.6176	0.4662	0.039*
C4	0.8881 (2)	0.6244 (3)	0.61917 (16)	0.0339 (4)
H4B	0.9332	0.5042	0.6448	0.041*
H4A	0.9852	0.6675	0.5972	0.041*
C5	0.5004 (3)	0.3162 (2)	0.82757 (16)	0.0352 (4)
H5B	0.4483	0.3527	0.8934	0.042*
H5A	0.5224	0.1968	0.8424	0.042*
C6	0.3794 (3)	0.4017 (2)	0.73268 (15)	0.0323 (4)
H6B	0.4310	0.3646	0.6669	0.039*
H6A	0.2721	0.3740	0.7491	0.039*
C7	0.9451 (3)	0.0645 (3)	0.6394 (2)	0.0439 (5)
H7A	0.9948	0.1495	0.6418	0.066*
H7B	1.0219	−0.0116	0.5998	0.066*
H7C	0.9287	0.0051	0.7137	0.066*
C8	0.7758 (2)	0.1420 (2)	0.58235 (14)	0.0237 (4)
O3	0.04893 (19)	0.6799 (2)	0.85583 (12)	0.0483 (4)
O4	0.22460 (17)	0.61095 (18)	0.99369 (11)	0.0365 (3)
C10	−0.0672 (3)	0.7447 (4)	1.0205 (2)	0.0597 (7)
H10A	−0.1743	0.7511	0.9897	0.089*
H10B	−0.0688	0.8543	1.0225	0.089*
H10C	−0.0541	0.6748	1.0945	0.089*
C9	0.0803 (2)	0.6732 (2)	0.95066 (15)	0.0296 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01854 (12)	0.02630 (12)	0.01684 (12)	−0.00952 (8)	−0.00280 (7)	−0.00334 (8)
O1	0.0436 (9)	0.0505 (10)	0.0869 (14)	−0.0293 (8)	−0.0231 (9)	0.0084 (9)
O2	0.0442 (9)	0.0309 (7)	0.0425 (8)	−0.0084 (6)	−0.0126 (7)	0.0001 (6)
N1	0.0240 (8)	0.0253 (7)	0.0212 (8)	−0.0076 (6)	−0.0048 (6)	−0.0036 (6)
N2	0.0278 (9)	0.0324 (9)	0.0351 (9)	−0.0129 (7)	−0.0124 (7)	0.0070 (7)
N3	0.0200 (7)	0.0323 (8)	0.0192 (7)	−0.0085 (6)	−0.0031 (6)	−0.0037 (6)
N4	0.0255 (8)	0.0348 (8)	0.0278 (8)	−0.0121 (7)	−0.0080 (6)	−0.0033 (7)
N5	0.0378 (10)	0.0412 (10)	0.0297 (9)	−0.0072 (8)	−0.0064 (7)	−0.0145 (7)
N6	0.0269 (8)	0.0349 (8)	0.0197 (7)	−0.0136 (7)	−0.0007 (6)	−0.0046 (6)
C1	0.0390 (11)	0.0288 (10)	0.0351 (11)	−0.0092 (8)	−0.0064 (8)	−0.0111 (8)
C2	0.0302 (10)	0.0241 (9)	0.0485 (12)	−0.0033 (8)	−0.0064 (9)	−0.0053 (8)
C3	0.0287 (10)	0.0441 (11)	0.0245 (9)	−0.0161 (8)	0.0034 (8)	−0.0024 (8)
C4	0.0189 (9)	0.0464 (11)	0.0353 (11)	−0.0124 (8)	−0.0004 (8)	−0.0048 (9)
C5	0.0522 (13)	0.0294 (10)	0.0279 (10)	−0.0190 (9)	−0.0047 (9)	−0.0039 (8)
C6	0.0405 (11)	0.0378 (10)	0.0272 (10)	−0.0232 (9)	−0.0016 (8)	−0.0082 (8)
C7	0.0281 (11)	0.0444 (12)	0.0550 (14)	−0.0076 (9)	−0.0158 (10)	−0.0040 (10)
C8	0.0206 (9)	0.0288 (9)	0.0219 (9)	−0.0070 (7)	−0.0007 (7)	−0.0074 (7)
O3	0.0350 (8)	0.0820 (12)	0.0282 (8)	−0.0173 (8)	−0.0063 (6)	−0.0130 (7)
O4	0.0259 (7)	0.0515 (8)	0.0289 (7)	−0.0102 (6)	−0.0066 (6)	−0.0041 (6)
C10	0.0354 (13)	0.087 (2)	0.0552 (16)	−0.0080 (12)	0.0065 (11)	−0.0303 (14)
C9	0.0246 (9)	0.0386 (10)	0.0260 (10)	−0.0118 (8)	−0.0010 (7)	−0.0060 (8)

Geometric parameters (Å, º)

Cu1—N3	2.0400 (15)	C1—C2	1.518 (3)
Cu1—N1	2.0461 (15)	C1—H1B	0.9900
Cu1—N4	2.0706 (16)	C1—H1A	0.9900
Cu1—N6	2.0765 (15)	C2—H2A	0.9900
Cu1—N2	2.3705 (16)	C2—H2B	0.9900
Cu1—N5	2.4123 (18)	C3—C4	1.509 (3)
O1—C8	1.232 (2)	C3—H3B	0.9900
O2—C8	1.243 (2)	C3—H3A	0.9900
N1—C1	1.471 (2)	C4—H4B	0.9900
N1—H1NB	0.867 (9)	C4—H4A	0.9900
N1—H1NA	0.863 (9)	C5—C6	1.514 (3)
N2—C2	1.460 (3)	C5—H5B	0.9900
N2—H2NB	0.866 (10)	C5—H5A	0.9900
N2—H2NA	0.862 (10)	C6—H6B	0.9900
N3—C3	1.472 (2)	C6—H6A	0.9900
N3—H3NB	0.863 (9)	C7—C8	1.507 (3)
N3—H3NA	0.857 (9)	C7—H7A	0.9800
N4—C4	1.472 (3)	C7—H7B	0.9800
N4—H4NB	0.865 (9)	C7—H7C	0.9800
N4—H4NA	0.862 (9)	O3—C9	1.238 (2)
N5—C5	1.464 (3)	O4—C9	1.253 (2)
N5—H5NB	0.865 (10)	C10—C9	1.514 (3)
N5—H5NA	0.869 (10)	C10—H10A	0.9800
N6—C6	1.469 (2)	C10—H10B	0.9800
N6—H6NB	0.867 (9)	C10—H10C	0.9800
N6—H6NA	0.863 (9)
N3—Cu1—N1	174.30 (6)	C2—C1—H1B	109.9
N3—Cu1—N4	83.22 (6)	N1—C1—H1A	109.9
N1—Cu1—N4	92.17 (6)	C2—C1—H1A	109.9
N3—Cu1—N6	89.57 (6)	H1B—C1—H1A	108.3
N1—Cu1—N6	95.10 (6)	N2—C2—C1	109.31 (16)
N4—Cu1—N6	172.68 (6)	N2—C2—H2A	109.8
N3—Cu1—N2	96.95 (6)	C1—C2—H2A	109.8
N1—Cu1—N2	79.80 (6)	N2—C2—H2B	109.8
N4—Cu1—N2	91.83 (6)	C1—C2—H2B	109.8
N6—Cu1—N2	90.25 (6)	H2A—C2—H2B	108.3
N3—Cu1—N5	95.62 (6)	N3—C3—C4	108.41 (15)
N1—Cu1—N5	88.48 (6)	N3—C3—H3B	110.0
N4—Cu1—N5	100.32 (6)	C4—C3—H3B	110.0
N6—Cu1—N5	79.11 (6)	N3—C3—H3A	110.0
N2—Cu1—N5	163.45 (6)	C4—C3—H3A	110.0
C1—N1—Cu1	110.49 (11)	H3B—C3—H3A	108.4
C1—N1—H1NB	106.9 (13)	N4—C4—C3	107.06 (15)
Cu1—N1—H1NB	112.4 (14)	N4—C4—H4B	110.3
C1—N1—H1NA	110.4 (13)	C3—C4—H4B	110.3
Cu1—N1—H1NA	108.4 (14)	N4—C4—H4A	110.3
H1NB—N1—H1NA	108.2 (19)	C3—C4—H4A	110.3
C2—N2—Cu1	103.17 (11)	H4B—C4—H4A	108.6
C2—N2—H2NB	112.3 (15)	N5—C5—C6	110.01 (16)
Cu1—N2—H2NB	114.1 (15)	N5—C5—H5B	109.7
C2—N2—H2NA	112.5 (16)	C6—C5—H5B	109.7
Cu1—N2—H2NA	109.0 (16)	N5—C5—H5A	109.7
H2NB—N2—H2NA	106 (2)	C6—C5—H5A	109.7
C3—N3—Cu1	109.69 (11)	H5B—C5—H5A	108.2
C3—N3—H3NB	108.5 (14)	N6—C6—C5	109.59 (15)
Cu1—N3—H3NB	109.9 (14)	N6—C6—H6B	109.8
C3—N3—H3NA	111.4 (14)	C5—C6—H6B	109.8
Cu1—N3—H3NA	108.2 (14)	N6—C6—H6A	109.8
H3NB—N3—H3NA	109.2 (19)	C5—C6—H6A	109.8
C4—N4—Cu1	106.50 (11)	H6B—C6—H6A	108.2
C4—N4—H4NB	110.4 (15)	C8—C7—H7A	109.5
Cu1—N4—H4NB	118.4 (15)	C8—C7—H7B	109.5
C4—N4—H4NA	107.6 (15)	H7A—C7—H7B	109.5
Cu1—N4—H4NA	106.3 (15)	C8—C7—H7C	109.5
H4NB—N4—H4NA	107 (2)	H7A—C7—H7C	109.5
C5—N5—Cu1	101.64 (12)	H7B—C7—H7C	109.5
C5—N5—H5NB	111.5 (16)	O1—C8—O2	123.50 (17)
Cu1—N5—H5NB	115.3 (16)	O1—C8—C7	118.44 (17)
C5—N5—H5NA	110.4 (16)	O2—C8—C7	117.99 (16)
Cu1—N5—H5NA	108.4 (15)	C9—C10—H10A	109.5
H5NB—N5—H5NA	109 (2)	C9—C10—H10B	109.5
C6—N6—Cu1	112.03 (12)	H10A—C10—H10B	109.5
C6—N6—H6NB	109.2 (14)	C9—C10—H10C	109.5
Cu1—N6—H6NB	113.4 (14)	H10A—C10—H10C	109.5
C6—N6—H6NA	109.0 (14)	H10B—C10—H10C	109.5
Cu1—N6—H6NA	109.7 (14)	O3—C9—O4	125.11 (18)
H6NB—N6—H6NA	103 (2)	O3—C9—C10	117.52 (19)
N1—C1—C2	109.09 (15)	O4—C9—C10	117.37 (18)
N1—C1—H1B	109.9
N3—Cu1—N1—C1	35.2 (6)	N3—Cu1—N5—C5	−103.95 (12)
N4—Cu1—N1—C1	71.09 (13)	N1—Cu1—N5—C5	80.02 (12)
N6—Cu1—N1—C1	−109.71 (12)	N4—Cu1—N5—C5	171.95 (11)
N2—Cu1—N1—C1	−20.38 (12)	N6—Cu1—N5—C5	−15.47 (11)
N5—Cu1—N1—C1	171.37 (13)	N2—Cu1—N5—C5	35.3 (3)
N3—Cu1—N2—C2	174.23 (11)	N3—Cu1—N6—C6	80.73 (12)
N1—Cu1—N2—C2	−10.51 (11)	N1—Cu1—N6—C6	−102.54 (12)
N4—Cu1—N2—C2	−102.38 (12)	N4—Cu1—N6—C6	71.1 (5)
N6—Cu1—N2—C2	84.63 (12)	N2—Cu1—N6—C6	177.68 (12)
N5—Cu1—N2—C2	35.1 (3)	N5—Cu1—N6—C6	−15.07 (12)
N1—Cu1—N3—C3	28.8 (7)	Cu1—N1—C1—C2	49.05 (19)
N4—Cu1—N3—C3	−7.34 (12)	Cu1—N2—C2—C1	38.40 (16)
N6—Cu1—N3—C3	173.89 (12)	N1—C1—C2—N2	−60.3 (2)
N2—Cu1—N3—C3	83.69 (12)	Cu1—N3—C3—C4	35.02 (18)
N5—Cu1—N3—C3	−107.10 (12)	Cu1—N4—C4—C3	46.65 (17)
N3—Cu1—N4—C4	−22.06 (12)	N3—C3—C4—N4	−54.8 (2)
N1—Cu1—N4—C4	161.30 (12)	Cu1—N5—C5—C6	42.63 (17)
N6—Cu1—N4—C4	−12.4 (5)	Cu1—N6—C6—C5	44.14 (19)
N2—Cu1—N4—C4	−118.84 (12)	N5—C5—C6—N6	−60.8 (2)
N5—Cu1—N4—C4	72.45 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NB···O4	0.87 (1)	2.06 (1)	2.917 (2)	170 (2)
N1—H1NA···O4^i	0.86 (1)	2.27 (1)	3.040 (2)	149 (2)
N2—H2NB···O1^ii	0.87 (1)	2.74 (2)	3.393 (3)	134 (2)
N2—H2NA···O1^iii	0.86 (1)	2.12 (1)	2.964 (2)	165 (2)
N3—H3NB···O2	0.86 (1)	2.09 (1)	2.933 (2)	167 (2)
N3—H3NA···O2^ii	0.86 (1)	2.32 (1)	3.085 (2)	150 (2)
N4—H4NB···O3^iv	0.87 (1)	2.15 (1)	2.945 (2)	153 (2)
N4—H4NA···O1^iii	0.86 (1)	2.22 (1)	3.062 (2)	165 (2)
N5—H5NB···O2	0.87 (1)	2.98 (2)	3.647 (2)	136 (2)
N5—H5NA···O4^i	0.87 (1)	2.13 (1)	2.956 (2)	159 (2)
N6—H6NB···O3	0.87 (1)	2.10 (1)	2.956 (2)	169 (2)
N6—H6NA···O2^ii	0.86 (1)	2.22 (1)	3.056 (2)	162 (2)

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

Tris(ethylenediamine-κ²N,N')zinc(II) diacetate (umd886)

Crystal data

[Zn(C2H8N2)3](C2H3O2)2	Z = 2
Mr = 363.77	F(000) = 388
Triclinic, P1	Dx = 1.368 Mg m^−3
a = 8.3223 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1059 (5) Å	Cell parameters from 9943 reflections
c = 12.7492 (7) Å	θ = 3.1–26.0°
α = 70.855 (2)°	µ = 1.41 mm^−1
β = 85.800 (2)°	T = 200 K
γ = 75.434 (2)°	Block, colourless
V = 883.34 (9) Å^3	0.50 × 0.40 × 0.40 mm

Data collection

Bruker CMOS diffractometer	3450 independent reflections
Radiation source: fine-focus sealed tube	3242 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 26.1°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→10
Tmin = 0.538, Tmax = 0.602	k = −11→11
14208 measured reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.020	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.051	w = 1/[σ^2(Fo^2) + (0.0238P)^2 + 0.3152P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.026
3450 reflections	Δρmax = 0.30 e Å^−3
229 parameters	Δρmin = −0.24 e Å^−3
12 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (2)

Special details

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. 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 > 2sigma(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
Zn1	0.564211 (18)	0.644619 (18)	0.713369 (12)	0.01994 (8)
O1	0.73399 (15)	0.04251 (14)	0.55873 (10)	0.0401 (3)
O2	0.71151 (18)	0.27798 (15)	0.57743 (14)	0.0605 (4)
N1	0.52981 (16)	0.68995 (15)	0.87028 (10)	0.0259 (3)
H1NB	0.4439 (16)	0.659 (2)	0.9049 (13)	0.031*
H1NA	0.6163 (16)	0.6385 (18)	0.9120 (12)	0.031*
N2	0.44734 (15)	0.90194 (14)	0.65359 (10)	0.0258 (3)
H2NB	0.3715 (17)	0.922 (2)	0.6044 (12)	0.031*
H2NA	0.5207 (18)	0.9544 (19)	0.6234 (13)	0.031*
N3	0.62038 (14)	0.62314 (14)	0.54859 (9)	0.0220 (2)
H3NB	0.636 (2)	0.5237 (12)	0.5542 (14)	0.026*
H3NA	0.5383 (16)	0.6788 (17)	0.5037 (12)	0.026*
N4	0.81600 (15)	0.68484 (15)	0.69240 (10)	0.0260 (3)
H4NB	0.8797 (19)	0.651 (2)	0.7505 (11)	0.031*
H4NA	0.807 (2)	0.7873 (11)	0.6653 (14)	0.031*
N5	0.63463 (17)	0.38640 (15)	0.79660 (11)	0.0301 (3)
H5NB	0.689 (2)	0.339 (2)	0.7518 (13)	0.036*
H5NA	0.6965 (19)	0.366 (2)	0.8537 (11)	0.036*
N6	0.32494 (16)	0.58718 (17)	0.70605 (11)	0.0306 (3)
H6NB	0.2521 (18)	0.623 (2)	0.7499 (13)	0.037*
H6NA	0.285 (2)	0.634 (2)	0.6392 (9)	0.037*
C1	0.5017 (2)	0.86365 (18)	0.84717 (13)	0.0338 (3)
H1B	0.6077	0.8963	0.8278	0.041*
H1A	0.4566	0.8926	0.9137	0.041*
C2	0.3789 (2)	0.94863 (19)	0.75082 (13)	0.0341 (3)
H2A	0.2717	0.9187	0.7714	0.041*
H2B	0.3590	1.0661	0.7330	0.041*
C3	0.77475 (17)	0.67284 (18)	0.50930 (12)	0.0267 (3)
H3B	0.7507	0.7909	0.4767	0.032*
H3A	0.8244	0.6258	0.4511	0.032*
C4	0.89558 (17)	0.61677 (19)	0.60607 (13)	0.0295 (3)
H4B	0.9247	0.4983	0.6362	0.035*
H4A	0.9987	0.6529	0.5810	0.035*
C5	0.4799 (2)	0.3337 (2)	0.83065 (13)	0.0369 (4)
H5B	0.4347	0.3634	0.8969	0.044*
H5A	0.5028	0.2158	0.8502	0.044*
C6	0.3544 (2)	0.4127 (2)	0.73609 (13)	0.0352 (4)
H6B	0.3971	0.3784	0.6711	0.042*
H6A	0.2491	0.3800	0.7591	0.042*
C7	0.9469 (2)	0.0720 (2)	0.65678 (17)	0.0451 (4)
H7A	0.9773	0.1587	0.6742	0.068*
H7B	1.0337	0.0282	0.6115	0.068*
H7C	0.9352	−0.0127	0.7259	0.068*
C8	0.78433 (17)	0.13645 (16)	0.59340 (11)	0.0235 (3)
O3	0.06083 (15)	0.67616 (17)	0.85582 (10)	0.0469 (3)
O4	0.23264 (13)	0.61786 (15)	0.99611 (9)	0.0386 (3)
C10	−0.0498 (2)	0.7418 (3)	1.01481 (18)	0.0599 (6)
H10A	−0.1529	0.7758	0.9716	0.090*
H10B	−0.0275	0.8341	1.0293	0.090*
H10C	−0.0610	0.6597	1.0855	0.090*
C9	0.09244 (18)	0.67346 (19)	0.95009 (12)	0.0297 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02054 (10)	0.02266 (10)	0.01683 (10)	−0.00357 (6)	−0.00355 (6)	−0.00704 (6)
O1	0.0490 (7)	0.0347 (6)	0.0405 (7)	−0.0163 (5)	−0.0155 (5)	−0.0092 (5)
O2	0.0593 (9)	0.0359 (7)	0.0863 (11)	0.0160 (6)	−0.0384 (8)	−0.0318 (7)
N1	0.0280 (6)	0.0290 (6)	0.0193 (6)	−0.0026 (5)	−0.0054 (5)	−0.0080 (5)
N2	0.0267 (6)	0.0257 (6)	0.0227 (6)	−0.0025 (5)	−0.0073 (5)	−0.0063 (5)
N3	0.0206 (6)	0.0263 (6)	0.0202 (6)	−0.0037 (5)	−0.0036 (4)	−0.0095 (5)
N4	0.0230 (6)	0.0300 (6)	0.0264 (6)	−0.0059 (5)	−0.0079 (5)	−0.0093 (5)
N5	0.0404 (7)	0.0270 (6)	0.0225 (6)	−0.0052 (5)	−0.0090 (5)	−0.0077 (5)
N6	0.0267 (6)	0.0447 (8)	0.0230 (6)	−0.0129 (6)	−0.0020 (5)	−0.0106 (6)
C1	0.0459 (9)	0.0322 (8)	0.0262 (8)	−0.0046 (7)	−0.0068 (7)	−0.0154 (6)
C2	0.0397 (9)	0.0275 (8)	0.0316 (8)	0.0037 (6)	−0.0062 (7)	−0.0124 (6)
C3	0.0249 (7)	0.0330 (8)	0.0230 (7)	−0.0069 (6)	0.0022 (5)	−0.0108 (6)
C4	0.0184 (7)	0.0365 (8)	0.0333 (8)	−0.0033 (6)	−0.0016 (6)	−0.0129 (7)
C5	0.0593 (11)	0.0338 (8)	0.0223 (7)	−0.0242 (8)	−0.0018 (7)	−0.0052 (6)
C6	0.0433 (9)	0.0477 (9)	0.0259 (7)	−0.0267 (8)	0.0033 (7)	−0.0157 (7)
C7	0.0340 (9)	0.0367 (9)	0.0607 (12)	−0.0091 (7)	−0.0215 (8)	−0.0054 (8)
C8	0.0217 (7)	0.0256 (7)	0.0228 (7)	−0.0070 (5)	−0.0010 (5)	−0.0060 (6)
O3	0.0355 (6)	0.0786 (9)	0.0280 (6)	−0.0117 (6)	−0.0080 (5)	−0.0186 (6)
O4	0.0277 (6)	0.0560 (7)	0.0282 (6)	−0.0060 (5)	−0.0085 (4)	−0.0096 (5)
C10	0.0402 (11)	0.0850 (16)	0.0530 (12)	−0.0019 (10)	0.0051 (9)	−0.0309 (12)
C9	0.0269 (7)	0.0364 (8)	0.0232 (7)	−0.0085 (6)	−0.0027 (6)	−0.0048 (6)

Geometric parameters (Å, º)

Zn1—N1	2.1570 (12)	C1—C2	1.521 (2)
Zn1—N3	2.1795 (11)	C1—H1B	0.9900
Zn1—N5	2.1816 (13)	C1—H1A	0.9900
Zn1—N2	2.1927 (12)	C2—H2A	0.9900
Zn1—N6	2.1979 (13)	C2—H2B	0.9900
Zn1—N4	2.1992 (12)	C3—C4	1.518 (2)
O1—C8	1.2482 (17)	C3—H3B	0.9900
O2—C8	1.2340 (18)	C3—H3A	0.9900
N1—C1	1.4702 (19)	C4—H4B	0.9900
N1—H1NB	0.873 (9)	C4—H4A	0.9900
N1—H1NA	0.862 (9)	C5—C6	1.516 (2)
N2—C2	1.4705 (19)	C5—H5B	0.9900
N2—H2NB	0.865 (9)	C5—H5A	0.9900
N2—H2NA	0.861 (9)	C6—H6B	0.9900
N3—C3	1.4683 (18)	C6—H6A	0.9900
N3—H3NB	0.861 (9)	C7—C8	1.509 (2)
N3—H3NA	0.862 (9)	C7—H7A	0.9800
N4—C4	1.4725 (19)	C7—H7B	0.9800
N4—H4NB	0.867 (9)	C7—H7C	0.9800
N4—H4NA	0.867 (9)	O3—C9	1.2402 (19)
N5—C5	1.473 (2)	O4—C9	1.2531 (18)
N5—H5NB	0.864 (9)	C10—C9	1.514 (2)
N5—H5NA	0.864 (9)	C10—H10A	0.9800
N6—C6	1.466 (2)	C10—H10B	0.9800
N6—H6NB	0.868 (9)	C10—H10C	0.9800
N6—H6NA	0.867 (9)
N1—Zn1—N3	171.96 (5)	C2—C1—H1B	110.0
N1—Zn1—N5	91.47 (5)	N1—C1—H1A	110.0
N3—Zn1—N5	93.65 (5)	C2—C1—H1A	110.0
N1—Zn1—N2	80.77 (5)	H1B—C1—H1A	108.4
N3—Zn1—N2	95.17 (5)	N2—C2—C1	109.05 (12)
N5—Zn1—N2	167.64 (5)	N2—C2—H2A	109.9
N1—Zn1—N6	97.84 (5)	C1—C2—H2A	109.9
N3—Zn1—N6	89.12 (5)	N2—C2—H2B	109.9
N5—Zn1—N6	80.45 (5)	C1—C2—H2B	109.9
N2—Zn1—N6	91.02 (5)	H2A—C2—H2B	108.3
N1—Zn1—N4	93.33 (5)	N3—C3—C4	109.35 (11)
N3—Zn1—N4	79.87 (4)	N3—C3—H3B	109.8
N5—Zn1—N4	97.39 (5)	C4—C3—H3B	109.8
N2—Zn1—N4	92.68 (5)	N3—C3—H3A	109.8
N6—Zn1—N4	168.66 (5)	C4—C3—H3A	109.8
C1—N1—Zn1	107.66 (9)	H3B—C3—H3A	108.3
C1—N1—H1NB	109.0 (11)	N4—C4—C3	108.38 (11)
Zn1—N1—H1NB	111.0 (12)	N4—C4—H4B	110.0
C1—N1—H1NA	111.1 (11)	C3—C4—H4B	110.0
Zn1—N1—H1NA	109.8 (11)	N4—C4—H4A	110.0
H1NB—N1—H1NA	108.2 (16)	C3—C4—H4A	110.0
C2—N2—Zn1	107.24 (9)	H4B—C4—H4A	108.4
C2—N2—H2NB	112.0 (11)	N5—C5—C6	109.39 (12)
Zn1—N2—H2NB	110.4 (11)	N5—C5—H5B	109.8
C2—N2—H2NA	109.1 (12)	C6—C5—H5B	109.8
Zn1—N2—H2NA	109.8 (12)	N5—C5—H5A	109.8
H2NB—N2—H2NA	108.4 (17)	C6—C5—H5A	109.8
C3—N3—Zn1	109.34 (8)	H5B—C5—H5A	108.2
C3—N3—H3NB	108.2 (11)	N6—C6—C5	109.23 (12)
Zn1—N3—H3NB	107.9 (11)	N6—C6—H6B	109.8
C3—N3—H3NA	111.9 (11)	C5—C6—H6B	109.8
Zn1—N3—H3NA	110.2 (11)	N6—C6—H6A	109.8
H3NB—N3—H3NA	109.2 (15)	C5—C6—H6A	109.8
C4—N4—Zn1	106.68 (8)	H6B—C6—H6A	108.3
C4—N4—H4NB	110.9 (12)	C8—C7—H7A	109.5
Zn1—N4—H4NB	118.4 (12)	C8—C7—H7B	109.5
C4—N4—H4NA	106.3 (12)	H7A—C7—H7B	109.5
Zn1—N4—H4NA	107.7 (12)	C8—C7—H7C	109.5
H4NB—N4—H4NA	106.2 (16)	H7A—C7—H7C	109.5
C5—N5—Zn1	107.04 (10)	H7B—C7—H7C	109.5
C5—N5—H5NB	110.3 (12)	O2—C8—O1	124.29 (14)
Zn1—N5—H5NB	110.1 (12)	O2—C8—C7	118.48 (13)
C5—N5—H5NA	110.7 (12)	O1—C8—C7	117.22 (13)
Zn1—N5—H5NA	109.6 (12)	C9—C10—H10A	109.5
H5NB—N5—H5NA	109.1 (17)	C9—C10—H10B	109.5
C6—N6—Zn1	107.98 (10)	H10A—C10—H10B	109.5
C6—N6—H6NB	110.3 (12)	C9—C10—H10C	109.5
Zn1—N6—H6NB	112.2 (12)	H10A—C10—H10C	109.5
C6—N6—H6NA	110.6 (12)	H10B—C10—H10C	109.5
Zn1—N6—H6NA	109.0 (12)	O3—C9—O4	125.10 (15)
H6NB—N6—H6NA	106.7 (17)	O3—C9—C10	117.38 (15)
N1—C1—C2	108.35 (12)	O4—C9—C10	117.51 (15)
N1—C1—H1B	110.0
N3—Zn1—N1—C1	42.4 (4)	N1—Zn1—N5—C5	80.33 (9)
N5—Zn1—N1—C1	171.99 (10)	N3—Zn1—N5—C5	−105.87 (9)
N2—Zn1—N1—C1	−17.69 (10)	N2—Zn1—N5—C5	29.6 (3)
N6—Zn1—N1—C1	−107.45 (10)	N6—Zn1—N5—C5	−17.38 (9)
N4—Zn1—N1—C1	74.50 (10)	N4—Zn1—N5—C5	173.88 (9)
N1—Zn1—N2—C2	−12.85 (10)	N1—Zn1—N6—C6	−102.59 (9)
N3—Zn1—N2—C2	174.15 (10)	N3—Zn1—N6—C6	81.44 (9)
N5—Zn1—N2—C2	38.8 (3)	N5—Zn1—N6—C6	−12.41 (9)
N6—Zn1—N2—C2	84.93 (10)	N2—Zn1—N6—C6	176.59 (9)
N4—Zn1—N2—C2	−105.79 (10)	N4—Zn1—N6—C6	67.5 (3)
N1—Zn1—N3—C3	23.2 (4)	Zn1—N1—C1—C2	44.88 (14)
N5—Zn1—N3—C3	−106.29 (9)	Zn1—N2—C2—C1	40.74 (15)
N2—Zn1—N3—C3	82.39 (9)	N1—C1—C2—N2	−58.83 (17)
N6—Zn1—N3—C3	173.34 (9)	Zn1—N3—C3—C4	37.57 (13)
N4—Zn1—N3—C3	−9.43 (9)	Zn1—N4—C4—C3	46.77 (13)
N1—Zn1—N4—C4	163.77 (9)	N3—C3—C4—N4	−57.74 (15)
N3—Zn1—N4—C4	−20.56 (9)	Zn1—N5—C5—C6	44.32 (14)
N5—Zn1—N4—C4	71.85 (10)	Zn1—N6—C6—C5	39.81 (14)
N2—Zn1—N4—C4	−115.33 (9)	N5—C5—C6—N6	−58.02 (17)
N6—Zn1—N4—C4	−6.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1NB···O4	0.87 (1)	2.08 (1)	2.9437 (17)	170 (2)
N1—H1NA···O4^i	0.86 (1)	2.31 (1)	3.0398 (17)	142 (2)
N2—H2NB···O1^ii	0.87 (1)	2.21 (1)	3.0293 (16)	158 (2)
N2—H2NA···O1^iii	0.86 (1)	2.13 (1)	2.9816 (18)	170 (2)
N3—H3NB···O2	0.86 (1)	2.09 (1)	2.9449 (17)	171 (2)
N3—H3NA···O2^ii	0.86 (1)	2.28 (1)	3.0775 (17)	155 (2)
N4—H4NB···O3^iv	0.87 (1)	2.19 (1)	2.9885 (16)	153 (2)
N4—H4NA···O1^iii	0.87 (1)	2.23 (1)	3.0642 (17)	163 (2)
N5—H5NB···O2	0.86 (1)	2.44 (1)	3.228 (2)	151 (2)
N5—H5NA···O4^i	0.86 (1)	2.11 (1)	2.9232 (16)	158 (2)
N6—H6NB···O3	0.87 (1)	2.08 (1)	2.9390 (18)	171 (2)
N6—H6NA···O2^ii	0.87 (1)	2.61 (1)	3.424 (2)	157 (2)

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