{5,5'-Dihydroxy-2,2'-[(2-hydroxypropane-1,3-diyl)bis(nitrilomethanylyli-dene)]diphenolato}nickel(II) dihydrate.

In the title complex, [Ni(C17H16N2O5)]·2H2O, the Ni(II) ion is four-coordinated by two azomethine N and two phenolato O atoms of the tetradentate Schiff base ligand in a slightly distorted square-planar geometry. In the six-membered ring containing the metal, the azomethine N atoms and the three C atoms of the connecting 1,3-di-amino-propane-2-ol, all atoms except the metal are disordered over two sets of sites with an occupacy ratio of 0.566 (3):0.434 (3). The central C atom of the major component is significantly out of the mean plane of the remaing atoms while the conformation of this ring in the minor component is noticeably different. In the crystal, O-H⋯O hydrogen bonds involving the lattice water mol-ecules and the hy-droxy groups are observed.

Related literature

For related structures, see: Averseng et al. (2001 ▶); Donmez et al. (2007 ▶). For ring-puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

[Ni(C17H16N2O5)]·2H2O

M = 423.06

Monoclinic,

a = 8.201 (1) Å

b = 17.887 (3) Å

c = 11.863 (2) Å

β = 92.444 (3)°

V = 1738.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.16 mm−1

T = 293 K

0.13 × 0.10 × 0.06 mm

Data collection

Bruker BREEZE CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.599, T max = 0.746

23452 measured reflections

4164 independent reflections

2986 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.093

S = 1.04

4164 reflections

263 parameters

18 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXP (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813026007/mw2116sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026007/mw2116Isup2.hkl

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

[Ni(C17H16N2O5)]·2H2O	F(000) = 880
Mr = 423.06	Dx = 1.616 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 692 reflections
a = 8.201 (1) Å	θ = 2.1–27.8°
b = 17.887 (3) Å	µ = 1.16 mm−1
c = 11.863 (2) Å	T = 293 K
β = 92.444 (3)°	Thin plate, brown
V = 1738.6 (5) Å3	0.13 × 0.10 × 0.06 mm
Z = 4

Bruker BREEZE CCD area-detector diffractometer	4164 independent reflections
Radiation source: fine-focus sealed tube	2986 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
ω–scan	θmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.599, Tmax = 0.746	k = −23→23
23452 measured reflections	l = −15→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0388P)2 + 0.7206P] where P = (Fo2 + 2Fc2)/3
4164 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.32 e Å−3
18 restraints	Δρmin = −0.35 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	Occ. (<1)
Ni1	0.76757 (3)	0.236496 (16)	0.93756 (3)	0.03859 (11)
N1	0.6337 (6)	0.1583 (3)	1.0070 (4)	0.0460 (10)	0.566 (3)
N1'	0.5940 (8)	0.1599 (4)	0.9475 (5)	0.0460 (10)	0.434 (3)
N2	0.9310 (2)	0.16644 (11)	0.88144 (19)	0.0466 (5)
O1	0.63064 (19)	0.31366 (9)	0.99584 (15)	0.0473 (4)
O2	0.88647 (18)	0.32255 (8)	0.89186 (15)	0.0450 (4)
O3	0.1513 (2)	0.43146 (10)	1.11744 (16)	0.0566 (5)
H3O	0.2114	0.4680	1.1241	0.068*
O4	1.3374 (2)	0.46782 (10)	0.78268 (19)	0.0716 (6)
H4O	1.2827	0.5012	0.8098	0.086*
O5	0.757 (6)	−0.0234 (7)	0.894 (3)	0.071 (5)	0.566 (3)
H5OA	0.7605	−0.0387	0.8291	0.085*	0.566 (3)
O5'	0.770 (8)	−0.0278 (9)	0.919 (4)	0.071 (5)	0.434 (3)
H5OB	0.8157	−0.0371	0.8607	0.085*	0.434 (3)
C1	0.4836 (3)	0.30825 (13)	1.0367 (2)	0.0394 (5)
C2	0.3974 (3)	0.37316 (13)	1.0600 (2)	0.0402 (5)
H2	0.4450	0.4196	1.0484	0.048*
C3	0.2424 (3)	0.36936 (14)	1.1002 (2)	0.0426 (6)
C4	0.1706 (3)	0.30072 (15)	1.1231 (2)	0.0514 (7)
H4	0.0676	0.2985	1.1528	0.062*
C5	0.2534 (3)	0.23743 (15)	1.1013 (2)	0.0522 (7)
H5	0.2057	0.1916	1.1165	0.063*
C6	0.4093 (3)	0.23866 (13)	1.0564 (2)	0.0445 (6)
C7	0.4929 (10)	0.1699 (5)	1.0482 (6)	0.048 (2)	0.566 (3)
H7A	0.4402	0.1282	1.0758	0.057*	0.566 (3)
C7'	0.4642 (14)	0.1703 (6)	1.0048 (8)	0.048 (2)	0.434 (3)
H7B	0.3984	0.1285	1.0139	0.057*	0.434 (3)
C8	1.0308 (3)	0.32654 (13)	0.84706 (19)	0.0370 (5)
C9	1.1033 (3)	0.39629 (13)	0.8323 (2)	0.0428 (6)
H9	1.0478	0.4394	0.8516	0.051*
C10	1.2565 (3)	0.40182 (14)	0.7892 (2)	0.0506 (7)
C11	1.3385 (3)	0.33891 (16)	0.7536 (3)	0.0620 (8)
H11	1.4395	0.3433	0.7215	0.074*
C12	1.2684 (3)	0.27072 (15)	0.7665 (3)	0.0556 (7)
H12	1.3227	0.2284	0.7423	0.067*
C13	1.1161 (3)	0.26237 (13)	0.8153 (2)	0.0419 (5)
C14	1.0606 (3)	0.18853 (14)	0.8326 (2)	0.0481 (6)
H14	1.1261	0.1508	0.8053	0.058*
C15	0.6836 (7)	0.0784 (2)	1.0058 (5)	0.0631 (12)	0.566 (3)
H15A	0.5904	0.0472	1.0213	0.076*	0.566 (3)
H15B	0.7669	0.0698	1.0649	0.076*	0.566 (3)
C15'	0.6172 (9)	0.0838 (3)	0.9034 (6)	0.0631 (12)	0.434 (3)
H15C	0.6092	0.0852	0.8216	0.076*	0.434 (3)
H15D	0.5304	0.0519	0.9287	0.076*	0.434 (3)
C16	0.7488 (11)	0.0567 (5)	0.8937 (5)	0.0492 (18)	0.566 (3)
H16A	0.6720	0.0731	0.8332	0.059*	0.566 (3)
C16'	0.7765 (14)	0.0510 (7)	0.9401 (9)	0.0492 (18)	0.434 (3)
H16B	0.7802	0.0553	1.0225	0.059*	0.434 (3)
C17	0.9129 (16)	0.0834 (5)	0.8700 (10)	0.053 (3)	0.566 (3)
H17A	0.9379	0.0689	0.7938	0.063*	0.566 (3)
H17B	0.9915	0.0592	0.9214	0.063*	0.566 (3)
C17'	0.927 (2)	0.0850 (7)	0.9064 (15)	0.053 (3)	0.434 (3)
H17C	0.9612	0.0589	0.8397	0.063*	0.434 (3)
H17D	1.0095	0.0754	0.9658	0.063*	0.434 (3)
O1W	0.6893 (2)	0.44265 (10)	0.82950 (17)	0.0640 (5)
H1W	0.7360	0.4051	0.8540	0.077*
H2W	0.5895	0.4409	0.8310	0.077*
O2W	0.8076 (2)	0.41714 (11)	0.1272 (2)	0.0741 (6)
H3W	0.7637	0.3886	0.0811	0.089*
H4W	0.9035	0.4214	0.1113	0.089*

	U11	U22	U33	U12	U13	U23
Ni1	0.03398 (17)	0.02135 (15)	0.0616 (2)	−0.00177 (12)	0.01543 (13)	−0.00026 (13)
N1	0.056 (3)	0.0281 (12)	0.056 (3)	−0.0013 (15)	0.020 (2)	0.001 (2)
N1'	0.056 (3)	0.0281 (12)	0.056 (3)	−0.0013 (15)	0.020 (2)	0.001 (2)
N2	0.0432 (11)	0.0274 (10)	0.0698 (14)	−0.0003 (8)	0.0094 (10)	−0.0024 (9)
O1	0.0345 (8)	0.0292 (8)	0.0802 (12)	−0.0041 (7)	0.0240 (8)	0.0010 (8)
O2	0.0334 (8)	0.0285 (8)	0.0745 (12)	−0.0016 (6)	0.0203 (8)	−0.0002 (8)
O3	0.0338 (9)	0.0478 (11)	0.0899 (14)	0.0001 (8)	0.0208 (9)	−0.0065 (10)
O4	0.0518 (11)	0.0453 (11)	0.1213 (17)	−0.0134 (9)	0.0476 (11)	−0.0103 (11)
O5	0.107 (7)	0.0272 (16)	0.082 (12)	−0.009 (3)	0.038 (10)	−0.002 (3)
O5'	0.107 (7)	0.0272 (16)	0.082 (12)	−0.009 (3)	0.038 (10)	−0.002 (3)
C1	0.0337 (11)	0.0353 (12)	0.0499 (14)	−0.0051 (9)	0.0112 (10)	0.0020 (10)
C2	0.0330 (11)	0.0314 (12)	0.0572 (15)	−0.0045 (9)	0.0117 (10)	0.0029 (10)
C3	0.0336 (12)	0.0433 (14)	0.0518 (14)	−0.0010 (10)	0.0107 (10)	−0.0011 (11)
C4	0.0346 (13)	0.0548 (16)	0.0664 (17)	−0.0081 (11)	0.0206 (12)	−0.0001 (13)
C5	0.0441 (14)	0.0437 (14)	0.0702 (17)	−0.0157 (12)	0.0187 (12)	0.0039 (13)
C6	0.0392 (12)	0.0344 (12)	0.0609 (15)	−0.0061 (10)	0.0147 (11)	0.0037 (11)
C7	0.052 (3)	0.0304 (14)	0.062 (6)	−0.0118 (19)	0.016 (4)	0.003 (3)
C7'	0.052 (3)	0.0304 (14)	0.062 (6)	−0.0118 (19)	0.016 (4)	0.003 (3)
C8	0.0300 (11)	0.0360 (12)	0.0457 (13)	−0.0004 (9)	0.0103 (10)	−0.0028 (10)
C9	0.0364 (12)	0.0330 (12)	0.0602 (15)	−0.0012 (10)	0.0164 (11)	−0.0032 (11)
C10	0.0426 (14)	0.0403 (14)	0.0705 (18)	−0.0093 (11)	0.0218 (12)	−0.0063 (12)
C11	0.0458 (15)	0.0545 (17)	0.088 (2)	−0.0060 (13)	0.0344 (14)	−0.0147 (15)
C12	0.0460 (14)	0.0447 (15)	0.0782 (19)	0.0008 (12)	0.0267 (13)	−0.0157 (14)
C13	0.0365 (12)	0.0346 (12)	0.0556 (15)	−0.0002 (10)	0.0116 (10)	−0.0079 (11)
C14	0.0408 (13)	0.0344 (13)	0.0700 (17)	0.0026 (10)	0.0133 (12)	−0.0108 (12)
C15	0.086 (3)	0.0290 (18)	0.077 (3)	0.0026 (19)	0.035 (3)	0.002 (2)
C15'	0.086 (3)	0.0290 (18)	0.077 (3)	0.0026 (19)	0.035 (3)	0.002 (2)
C16	0.069 (4)	0.0227 (19)	0.057 (6)	−0.003 (2)	0.012 (4)	0.001 (4)
C16'	0.069 (4)	0.0227 (19)	0.057 (6)	−0.003 (2)	0.012 (4)	0.001 (4)
C17	0.058 (3)	0.0264 (13)	0.075 (8)	0.0046 (14)	0.011 (5)	−0.005 (3)
C17'	0.058 (3)	0.0264 (13)	0.075 (8)	0.0046 (14)	0.011 (5)	−0.005 (3)
O1W	0.0493 (11)	0.0433 (11)	0.0997 (16)	0.0012 (8)	0.0081 (10)	0.0162 (10)
O2W	0.0406 (10)	0.0589 (13)	0.1241 (19)	−0.0093 (9)	0.0197 (11)	−0.0314 (12)

Ni1—O2	1.9129 (15)	C6—C7'	1.448 (10)
Ni1—O1	1.9262 (15)	C7—H7A	0.9300
Ni1—N2	1.9713 (19)	C7'—H7B	0.9300
Ni1—N1	1.980 (5)	C8—C9	1.396 (3)
Ni1—N1'	1.983 (7)	C8—C13	1.404 (3)
N1—C7	1.290 (8)	C9—C10	1.380 (3)
N1—C15	1.486 (6)	C9—H9	0.9300
N1'—C7'	1.300 (10)	C10—C11	1.386 (3)
N1'—C15'	1.474 (9)	C11—C12	1.360 (4)
N2—C14	1.294 (3)	C11—H11	0.9300
N2—C17'	1.487 (12)	C12—C13	1.407 (3)
N2—C17	1.498 (9)	C12—H12	0.9300
O1—C1	1.322 (3)	C13—C14	1.415 (3)
O2—C8	1.320 (2)	C14—H14	0.9300
O3—C3	1.359 (3)	C15—C16	1.505 (8)
O3—H3O	0.8200	C15—H15A	0.9700
O4—C10	1.358 (3)	C15—H15B	0.9700
O4—H4O	0.8200	C15'—C16'	1.481 (10)
O5—C16	1.433 (10)	C15'—H15C	0.9700
O5—H5OA	0.8200	C15'—H15D	0.9700
O5'—C16'	1.432 (13)	C16—C17	1.466 (9)
O5'—H5OB	0.8200	C16—H16A	0.9800
C1—C2	1.393 (3)	C16'—C17'	1.449 (12)
C1—C6	1.410 (3)	C16'—H16B	0.9800
C2—C3	1.378 (3)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.393 (3)	C17'—H17C	0.9700
C4—C5	1.350 (4)	C17'—H17D	0.9700
C4—H4	0.9300	O1W—H1W	0.8201
C5—C6	1.406 (3)	O1W—H2W	0.8200
C5—H5	0.9300	O2W—H3W	0.8200
C6—C7	1.413 (8)	O2W—H4W	0.8200
O2—Ni1—O1	80.63 (7)	C10—C9—H9	119.7
O2—Ni1—N2	93.08 (8)	C8—C9—H9	119.7
O1—Ni1—N2	172.70 (7)	O4—C10—C9	122.5 (2)
O2—Ni1—N1	170.11 (14)	O4—C10—C11	116.3 (2)
O1—Ni1—N1	90.86 (14)	C9—C10—C11	121.1 (2)
N2—Ni1—N1	95.06 (15)	C12—C11—C10	118.7 (2)
O2—Ni1—N1'	161.6 (2)	C12—C11—H11	120.6
O1—Ni1—N1'	92.43 (19)	C10—C11—H11	120.6
N2—Ni1—N1'	94.7 (2)	C11—C12—C13	121.9 (2)
C7—N1—C15	114.3 (5)	C11—C12—H12	119.0
C7—N1—Ni1	124.4 (5)	C13—C12—H12	119.0
C15—N1—Ni1	121.2 (3)	C8—C13—C12	119.0 (2)
C7'—N1'—C15'	116.0 (7)	C8—C13—C14	123.9 (2)
C7'—N1'—Ni1	122.6 (7)	C12—C13—C14	117.1 (2)
C15'—N1'—Ni1	120.9 (5)	N2—C14—C13	128.7 (2)
C14—N2—C17'	114.4 (7)	N2—C14—H14	115.6
C14—N2—C17	110.0 (5)	C13—C14—H14	115.6
C14—N2—Ni1	122.71 (16)	N1—C15—C16	111.4 (5)
C17'—N2—Ni1	122.4 (7)	N1—C15—H15A	109.3
C17—N2—Ni1	126.5 (5)	C16—C15—H15A	109.3
C1—O1—Ni1	129.33 (14)	N1—C15—H15B	109.3
C8—O2—Ni1	129.38 (14)	C16—C15—H15B	109.3
C3—O3—H3O	109.5	H15A—C15—H15B	108.0
C10—O4—H4O	109.5	N1'—C15'—C16'	112.8 (7)
C16—O5—H5OA	109.6	N1'—C15'—H15C	109.0
C16'—O5'—H5OB	109.2	C16'—C15'—H15C	109.0
O1—C1—C2	119.4 (2)	N1'—C15'—H15D	109.0
O1—C1—C6	122.2 (2)	C16'—C15'—H15D	109.0
C2—C1—C6	118.4 (2)	H15C—C15'—H15D	107.8
C3—C2—C1	120.7 (2)	O5—C16—C17	107 (2)
C3—C2—H2	119.6	O5—C16—C15	105.8 (15)
C1—C2—H2	119.6	C17—C16—C15	116.7 (8)
O3—C3—C2	122.2 (2)	O5—C16—H16A	109.2
O3—C3—C4	116.8 (2)	C17—C16—H16A	109.2
C2—C3—C4	121.0 (2)	C15—C16—H16A	109.2
C5—C4—C3	118.8 (2)	O5'—C16'—C17'	113 (3)
C5—C4—H4	120.6	O5'—C16'—C15'	108 (3)
C3—C4—H4	120.6	C17'—C16'—C15'	120.3 (10)
C4—C5—C6	122.1 (2)	O5'—C16'—H16B	104.5
C4—C5—H5	118.9	C17'—C16'—H16B	104.5
C6—C5—H5	118.9	C15'—C16'—H16B	104.5
C5—C6—C1	118.9 (2)	C16—C17—N2	113.2 (9)
C5—C6—C7	117.7 (4)	C16—C17—H17A	108.9
C1—C6—C7	122.8 (4)	N2—C17—H17A	108.9
C5—C6—C7'	116.8 (5)	C16—C17—H17B	108.9
C1—C6—C7'	122.1 (5)	N2—C17—H17B	108.9
N1—C7—C6	127.7 (7)	H17A—C17—H17B	107.7
N1—C7—H7A	116.1	C16'—C17'—N2	119.4 (13)
C6—C7—H7A	116.1	C16'—C17'—H17C	107.5
N1'—C7'—C6	128.1 (10)	N2—C17'—H17C	107.5
N1'—C7'—H7B	115.9	C16'—C17'—H17D	107.5
C6—C7'—H7B	115.9	N2—C17'—H17D	107.5
O2—C8—C9	119.52 (19)	H17C—C17'—H17D	107.0
O2—C8—C13	122.0 (2)	H1W—O1W—H2W	114.4
C9—C8—C13	118.5 (2)	H3W—O2W—H4W	107.6
C10—C9—C8	120.6 (2)
O1—Ni1—N1—C7	12.6 (5)	Ni1—N1—C7—C6	−2.5 (9)
N2—Ni1—N1—C7	−171.6 (5)	C5—C6—C7—N1	177.9 (5)
N1'—Ni1—N1—C7	−81.7 (9)	C1—C6—C7—N1	−11.2 (8)
O1—Ni1—N1—C15	−173.2 (4)	C7'—C6—C7—N1	84 (2)
N2—Ni1—N1—C15	2.6 (4)	C15'—N1'—C7'—C6	−179.1 (8)
N1'—Ni1—N1—C15	92.5 (8)	Ni1—N1'—C7'—C6	9.5 (13)
O2—Ni1—N1'—C7'	−81.6 (9)	C5—C6—C7'—N1'	171.9 (8)
O1—Ni1—N1'—C7'	−14.4 (7)	C1—C6—C7'—N1'	8.9 (12)
N2—Ni1—N1'—C7'	163.9 (7)	C7—C6—C7'—N1'	−90 (2)
N1—Ni1—N1'—C7'	71.9 (9)	Ni1—O2—C8—C9	−172.50 (17)
O2—Ni1—N1'—C15'	107.4 (7)	Ni1—O2—C8—C13	6.3 (3)
O1—Ni1—N1'—C15'	174.5 (5)	O2—C8—C9—C10	177.8 (2)
N2—Ni1—N1'—C15'	−7.2 (5)	C13—C8—C9—C10	−1.1 (4)
N1—Ni1—N1'—C15'	−99.1 (10)	C8—C9—C10—O4	−174.1 (3)
O2—Ni1—N2—C14	−0.8 (2)	C8—C9—C10—C11	3.7 (4)
N1—Ni1—N2—C14	−175.2 (3)	O4—C10—C11—C12	175.0 (3)
N1'—Ni1—N2—C14	162.4 (3)	C9—C10—C11—C12	−2.9 (5)
O2—Ni1—N2—C17'	170.2 (9)	C10—C11—C12—C13	−0.4 (5)
N1—Ni1—N2—C17'	−4.2 (9)	O2—C8—C13—C12	179.1 (2)
N1'—Ni1—N2—C17'	−26.6 (9)	C9—C8—C13—C12	−2.1 (4)
O2—Ni1—N2—C17	−169.7 (6)	O2—C8—C13—C14	−3.0 (4)
N1—Ni1—N2—C17	16.0 (6)	C9—C8—C13—C14	175.8 (2)
N1'—Ni1—N2—C17	−6.4 (7)	C11—C12—C13—C8	2.9 (4)
O2—Ni1—O1—C1	169.3 (2)	C11—C12—C13—C14	−175.2 (3)
N1—Ni1—O1—C1	−15.8 (3)	C17'—N2—C14—C13	−167.9 (8)
N1'—Ni1—O1—C1	6.5 (3)	C17—N2—C14—C13	174.3 (6)
O1—Ni1—O2—C8	172.1 (2)	Ni1—N2—C14—C13	3.8 (4)
N2—Ni1—O2—C8	−4.1 (2)	C8—C13—C14—N2	−2.3 (5)
N1'—Ni1—O2—C8	−118.9 (6)	C12—C13—C14—N2	175.6 (3)
Ni1—O1—C1—C2	−171.24 (17)	C7—N1—C15—C16	133.4 (6)
Ni1—O1—C1—C6	8.0 (4)	Ni1—N1—C15—C16	−41.3 (7)
O1—C1—C2—C3	178.5 (2)	C7'—N1'—C15'—C16'	−124.1 (9)
C6—C1—C2—C3	−0.8 (4)	Ni1—N1'—C15'—C16'	47.5 (8)
C1—C2—C3—O3	−176.0 (2)	N1—C15—C16—O5	−167.0 (19)
C1—C2—C3—C4	2.8 (4)	N1—C15—C16—C17	74.6 (9)
O3—C3—C4—C5	176.4 (2)	N1'—C15'—C16'—O5'	165 (2)
C2—C3—C4—C5	−2.4 (4)	N1'—C15'—C16'—C17'	−63.0 (13)
C3—C4—C5—C6	0.0 (4)	O5—C16—C17—N2	−172.5 (14)
C4—C5—C6—C1	2.0 (4)	C15—C16—C17—N2	−54.6 (11)
C4—C5—C6—C7	173.2 (4)	C14—N2—C17—C16	−163.7 (6)
C4—C5—C6—C7'	−161.6 (5)	C17'—N2—C17—C16	88 (4)
O1—C1—C6—C5	179.2 (2)	Ni1—N2—C17—C16	6.4 (11)
C2—C1—C6—C5	−1.5 (4)	O5'—C16'—C17'—N2	157 (2)
O1—C1—C6—C7	8.4 (5)	C15'—C16'—C17'—N2	27.0 (19)
C2—C1—C6—C7	−172.3 (4)	C14—N2—C17'—C16'	−167.9 (10)
O1—C1—C6—C7'	−18.2 (6)	C17—N2—C17'—C16'	−89 (4)
C2—C1—C6—C7'	161.1 (5)	Ni1—N2—C17'—C16'	20.5 (17)
C15—N1—C7—C6	−177.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2	0.82	1.96	2.770 (2)	167
O1W—H1W···O1	0.82	2.53	3.087 (2)	127
O1W—H2W···O4i	0.82	2.18	2.951 (3)	158
O2W—H3W···O1ii	0.82	1.98	2.787 (3)	168
O2W—H4W···O3iii	0.82	2.04	2.837 (2)	165
O3—H3O···O1Wiv	0.82	1.87	2.665 (3)	165
O4—H4O···O2Wv	0.82	1.81	2.626 (3)	171
O5—H5OA···O1Wvi	0.82	1.97	2.78 (3)	166
O5′—H5OB···O1Wvi	0.82	2.28	3.03 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2	0.82	1.96	2.770 (2)	167
O1W—H1W⋯O1	0.82	2.53	3.087 (2)	127
O1W—H2W⋯O4i	0.82	2.18	2.951 (3)	158
O2W—H3W⋯O1ii	0.82	1.98	2.787 (3)	168
O2W—H4W⋯O3iii	0.82	2.04	2.837 (2)	165
O3—H3O⋯O1W iv	0.82	1.87	2.665 (3)	165
O4—H4O⋯O2W v	0.82	1.81	2.626 (3)	171
O5—H5OA⋯O1W vi	0.82	1.97	2.78 (3)	166
O5′—H5OB⋯O1W vi	0.82	2.28	3.03 (4)	151

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