{2-[(S)-({2-[(S)-1-Benzyl-pyrrolidine-2-carboxamido]phen-yl}(phen-yl)methyl-ene)amino]-4-hydroxy-butanoato-κN,N',N'',O}nickel(II).

The central Ni atom of the title compound, [Ni(C(29)H(29)N(3)O(4))], is coordinated by three N atoms [Ni-N = 1.955 (2), 1.844 (2) and 1.872 (2) Å] and by one O atom [Ni-O = 1.862 (2) Å] in a pseudo-square-planar geometry. The conformation of the hydroxy-butanoate side chain is controlled by a strong intra-molecular hydrogen bond (H⋯O = 1.84 Å).

Related literature

For related literature, see: Belokon (1992 ▶); Belokon et al. (1988 ▶); Carducci et al. (2006 ▶); Chung et al. (1993 ▶); Gu et al. (2004 ▶); Jirman & Popkov (1995 ▶); Jirman et al. (1998 ▶); Kožíšek et al. (2004 ▶); Langer et al. (2007 ▶); Nádvorník & Popkov (2002 ▶); Popkov et al. (2003 ▶, 2005 ▶, and references therein).

Experimental

Crystal data

[Ni(C29H29N3O4)]

M = 542.26

Orthorhombic,

a = 9.743 (1) Å

b = 10.222 (1) Å

c = 26.016 (1) Å

V = 2591.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.79 mm−1

T = 100 (2) K

0.25 × 0.19 × 0.16 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (Clark & Reid, 1995 ▶) T min = 0.840, T max = 0.897

62972 measured reflections

5273 independent reflections

4968 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.073

S = 1.08

5273 reflections

337 parameters

112 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.81 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: (Flack, 1983 ▶), 2260 Friedel pairs

Flack parameter: 0.04 (1)

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000949/sg2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808000949/sg2215Isup2.hkl

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

[Ni(C29H29N3O4)]	F(000) = 1136
Mr = 542.26	Dx = 1.390 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 35886 reflections
a = 9.743 (1) Å	θ = 3.2–35.3°
b = 10.222 (1) Å	µ = 0.79 mm−1
c = 26.016 (1) Å	T = 100 K
V = 2591.0 (4) Å3	Block, orange
Z = 4	0.25 × 0.19 × 0.16 mm

Oxford Diffraction Gemini R CCD diffractometer	5273 independent reflections
Radiation source: fine-focus sealed tube	4968 reflections with I > 2σ(I)
graphite	Rint = 0.038
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 4.2°
Absorption correction: analytical (Clark & Reid, 1995)	h = −12→12
Tmin = 0.840, Tmax = 0.897	k = −12→12
62972 measured reflections	l = −32→32

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0343P)2 + 1.651P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
5273 reflections	Δρmax = 0.81 e Å−3
337 parameters	Δρmin = −0.29 e Å−3
112 restraints	Absolute structure: (Flack, 1983), 2260 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (1)

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006)

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	1.1251 (2)	0.7826 (2)	0.09762 (9)	0.0266 (5)
H1B	1.1797	0.8305	0.1236	0.032*
H1A	1.1836	0.7650	0.0673	0.032*
C2	1.0675 (3)	0.6558 (3)	0.11981 (10)	0.0298 (6)
H2B	1.0323	0.6690	0.1551	0.036*
H2A	1.1378	0.5859	0.1202	0.036*
C3	0.9499 (3)	0.6230 (2)	0.08195 (10)	0.0292 (5)
H3B	0.8700	0.5860	0.1005	0.035*
H3A	0.9808	0.5593	0.0557	0.035*
C4	0.9116 (3)	0.7574 (2)	0.05630 (8)	0.0212 (5)
H4A	0.9335	0.7550	0.0188	0.025*
C5	0.7633 (2)	0.7917 (2)	0.06404 (8)	0.0207 (5)
C6	0.6196 (2)	0.9454 (2)	0.11106 (8)	0.0191 (4)
C7	0.5289 (2)	0.9622 (3)	0.06902 (9)	0.0249 (5)
H7A	0.5496	0.9228	0.0369	0.030*
C8	0.4110 (3)	1.0349 (3)	0.07429 (10)	0.0307 (5)
H8A	0.3517	1.0467	0.0457	0.037*
C9	0.3781 (3)	1.0920 (3)	0.12203 (10)	0.0358 (6)
H9A	0.2956	1.1408	0.1254	0.043*
C10	0.4646 (2)	1.0779 (3)	0.16439 (10)	0.0298 (5)
H10A	0.4405	1.1165	0.1964	0.036*
C11	0.5877 (2)	1.0065 (2)	0.15983 (8)	0.0208 (5)
C12	0.6754 (2)	1.0000 (2)	0.20620 (9)	0.0200 (5)
C13	0.6158 (3)	1.0400 (2)	0.25796 (8)	0.0220 (5)
C14	0.5219 (3)	0.9572 (3)	0.28276 (10)	0.0327 (6)
H14A	0.4997	0.8746	0.2682	0.039*
C15	0.4606 (3)	0.9970 (3)	0.32928 (11)	0.0388 (7)
H15A	0.3980	0.9401	0.3461	0.047*
C16	0.4906 (3)	1.1192 (3)	0.35113 (10)	0.0371 (6)
H16A	0.4479	1.1456	0.3823	0.045*
C17	0.5839 (3)	1.2014 (3)	0.32650 (10)	0.0318 (6)
H17A	0.6053	1.2842	0.3410	0.038*
C18	0.6471 (2)	1.1622 (3)	0.28005 (10)	0.0267 (5)
H18A	0.7109	1.2186	0.2636	0.032*
C19	0.8890 (3)	0.9518 (2)	0.24976 (8)	0.0210 (4)
H19A	0.8642	1.0219	0.2749	0.025*
C20	1.0355 (3)	0.9710 (2)	0.23118 (9)	0.0239 (5)
C21	1.0390 (2)	0.9727 (2)	0.04879 (10)	0.0237 (5)
H21B	1.0992	1.0318	0.0688	0.028*
H21A	1.0936	0.9389	0.0196	0.028*
C22	0.9215 (2)	1.0526 (2)	0.02739 (9)	0.0204 (5)
C23	0.8585 (3)	1.1494 (2)	0.05785 (10)	0.0280 (5)
H23A	0.8897	1.1659	0.0918	0.034*
C24	0.7494 (3)	1.2206 (3)	0.03723 (15)	0.0481 (8)
H24A	0.7042	1.2847	0.0575	0.058*
C25	0.7059 (3)	1.1975 (3)	−0.01382 (18)	0.0618 (11)
H25A	0.6310	1.2457	−0.0275	0.074*
C26	0.7713 (4)	1.1055 (3)	−0.04396 (15)	0.0617 (11)
H26A	0.7433	1.0926	−0.0786	0.074*
C27	0.8778 (4)	1.0321 (3)	−0.02365 (10)	0.0393 (7)
H27A	0.9217	0.9677	−0.0442	0.047*
C28	0.8688 (3)	0.8146 (2)	0.27477 (9)	0.0287 (6)
H28B	0.7705	0.8042	0.2836	0.034*
H28A	0.8915	0.7470	0.2489	0.034*
C29	0.9549 (3)	0.7881 (3)	0.32357 (11)	0.0346 (6)
H29B	0.9454	0.8638	0.3470	0.041*
H29A	0.9167	0.7106	0.3413	0.041*
N1	0.99995 (19)	0.8581 (2)	0.08284 (7)	0.0204 (4)
N2	0.7433 (2)	0.87954 (18)	0.10419 (7)	0.0184 (4)
N3	0.80154 (19)	0.96293 (18)	0.20289 (7)	0.0181 (4)
Ni1	0.89673 (3)	0.91512 (3)	0.143270 (10)	0.01780 (8)
O1	0.67597 (18)	0.73706 (18)	0.03689 (6)	0.0271 (4)
O2	1.05357 (17)	0.95424 (18)	0.18116 (7)	0.0261 (4)
O3	1.12652 (18)	0.99616 (19)	0.26255 (7)	0.0324 (4)
O4	1.0957 (2)	0.7663 (2)	0.31439 (8)	0.0480 (5)
H4W	1.1334 (14)	0.8443 (19)	0.3004 (11)	0.058*

	U11	U22	U33	U12	U13	U23
C1	0.0218 (12)	0.0316 (13)	0.0265 (11)	0.0112 (10)	−0.0007 (9)	0.0017 (10)
C2	0.0376 (15)	0.0261 (13)	0.0258 (12)	0.0120 (11)	0.0002 (10)	0.0024 (10)
C3	0.0357 (13)	0.0230 (13)	0.0290 (12)	0.0036 (10)	0.0032 (10)	0.0033 (10)
C4	0.0257 (12)	0.0194 (11)	0.0186 (10)	0.0041 (10)	0.0031 (9)	0.0000 (8)
C5	0.0244 (11)	0.0196 (11)	0.0180 (10)	−0.0018 (9)	0.0023 (9)	−0.0010 (9)
C6	0.0163 (10)	0.0217 (11)	0.0192 (10)	−0.0045 (9)	0.0020 (8)	0.0020 (8)
C7	0.0169 (11)	0.0349 (13)	0.0229 (11)	−0.0022 (10)	0.0021 (9)	0.0009 (10)
C8	0.0173 (11)	0.0444 (15)	0.0304 (12)	0.0019 (11)	−0.0059 (10)	0.0041 (11)
C9	0.0219 (12)	0.0484 (16)	0.0372 (13)	0.0101 (13)	−0.0022 (10)	−0.0050 (13)
C10	0.0180 (11)	0.0410 (15)	0.0305 (12)	0.0064 (12)	0.0012 (9)	−0.0086 (12)
C11	0.0172 (11)	0.0230 (11)	0.0221 (10)	−0.0020 (9)	0.0004 (9)	−0.0020 (8)
C12	0.0201 (11)	0.0187 (11)	0.0213 (11)	−0.0022 (9)	0.0017 (9)	−0.0030 (9)
C13	0.0205 (11)	0.0260 (11)	0.0194 (10)	0.0033 (10)	−0.0005 (9)	−0.0048 (8)
C14	0.0342 (14)	0.0338 (14)	0.0300 (13)	−0.0007 (11)	0.0077 (11)	−0.0042 (11)
C15	0.0359 (15)	0.0488 (18)	0.0317 (14)	0.0007 (13)	0.0116 (12)	−0.0010 (13)
C16	0.0351 (14)	0.0528 (17)	0.0234 (12)	0.0185 (12)	0.0014 (11)	−0.0074 (12)
C17	0.0257 (13)	0.0383 (14)	0.0313 (13)	0.0151 (11)	−0.0080 (10)	−0.0153 (11)
C18	0.0213 (12)	0.0271 (13)	0.0318 (13)	0.0071 (10)	−0.0047 (10)	−0.0057 (10)
C19	0.0225 (11)	0.0204 (11)	0.0201 (10)	0.0026 (10)	−0.0030 (9)	−0.0032 (8)
C20	0.0238 (12)	0.0206 (12)	0.0272 (12)	0.0015 (10)	−0.0034 (10)	0.0004 (9)
C21	0.0180 (11)	0.0256 (12)	0.0277 (12)	0.0014 (10)	0.0054 (10)	0.0042 (10)
C22	0.0187 (11)	0.0196 (11)	0.0229 (10)	−0.0043 (8)	0.0001 (8)	0.0047 (8)
C23	0.0295 (14)	0.0213 (12)	0.0333 (13)	0.0010 (10)	0.0065 (10)	0.0029 (10)
C24	0.0300 (14)	0.0269 (15)	0.088 (2)	0.0076 (12)	0.0157 (16)	0.0203 (15)
C25	0.0363 (17)	0.0403 (19)	0.109 (3)	−0.0102 (14)	−0.0359 (19)	0.040 (2)
C26	0.085 (3)	0.0305 (18)	0.069 (2)	−0.0197 (17)	−0.054 (2)	0.0208 (15)
C27	0.065 (2)	0.0250 (13)	0.0283 (13)	−0.0059 (14)	−0.0126 (14)	0.0033 (10)
C28	0.0347 (15)	0.0225 (12)	0.0289 (12)	0.0039 (10)	0.0014 (10)	0.0015 (10)
C29	0.0317 (13)	0.0392 (16)	0.0328 (14)	0.0095 (12)	0.0071 (11)	0.0141 (12)
N1	0.0174 (9)	0.0215 (10)	0.0221 (9)	0.0029 (8)	0.0009 (7)	0.0032 (8)
N2	0.0185 (9)	0.0221 (10)	0.0148 (8)	0.0003 (7)	0.0016 (7)	0.0009 (7)
N3	0.0172 (9)	0.0166 (9)	0.0205 (9)	−0.0007 (7)	−0.0017 (7)	−0.0011 (7)
Ni1	0.01522 (12)	0.02042 (13)	0.01776 (12)	0.00077 (11)	0.00044 (11)	−0.00103 (11)
O1	0.0277 (9)	0.0332 (10)	0.0204 (8)	−0.0057 (8)	0.0002 (7)	−0.0052 (7)
O2	0.0178 (8)	0.0332 (10)	0.0272 (8)	0.0001 (7)	−0.0009 (7)	−0.0035 (7)
O3	0.0254 (10)	0.0390 (11)	0.0328 (9)	−0.0015 (8)	−0.0097 (8)	−0.0034 (8)
O4	0.0386 (11)	0.0538 (13)	0.0516 (12)	0.0148 (11)	0.0041 (11)	0.0190 (10)

C1—N1	1.494 (3)	C16—H16A	0.9500
C1—C2	1.526 (4)	C17—C18	1.414 (3)
C1—H1B	0.9900	C17—H17A	0.9500
C1—H1A	0.9900	C18—H18A	0.9500
C2—C3	1.548 (4)	C19—N3	1.492 (3)
C2—H2B	0.9900	C19—C20	1.519 (3)
C2—H2A	0.9900	C19—C28	1.559 (3)
C3—C4	1.573 (3)	C19—H19A	1.0000
C3—H3B	0.9900	C20—O3	1.232 (3)
C3—H3A	0.9900	C20—O2	1.324 (3)
C4—C5	1.501 (3)	C21—C22	1.512 (3)
C4—N1	1.509 (3)	C21—N1	1.517 (3)
C4—H4A	1.0000	C21—H21B	0.9900
C5—O1	1.239 (3)	C21—H21A	0.9900
C5—N2	1.391 (3)	C22—C23	1.408 (3)
C6—N2	1.392 (3)	C22—C27	1.410 (3)
C6—C7	1.417 (3)	C23—C24	1.396 (4)
C6—C11	1.448 (3)	C23—H23A	0.9500
C7—C8	1.374 (4)	C24—C25	1.414 (6)
C7—H7A	0.9500	C24—H24A	0.9500
C8—C9	1.409 (4)	C25—C26	1.380 (6)
C8—H8A	0.9500	C25—H25A	0.9500
C9—C10	1.395 (4)	C26—C27	1.386 (5)
C9—H9A	0.9500	C26—H26A	0.9500
C10—C11	1.409 (3)	C27—H27A	0.9500
C10—H10A	0.9500	C28—C29	1.546 (4)
C11—C12	1.480 (3)	C28—H28B	0.9900
C12—N3	1.289 (3)	C28—H28A	0.9900
C12—C13	1.522 (3)	C29—O4	1.409 (4)
C13—C14	1.403 (4)	C29—H29B	0.9900
C13—C18	1.408 (3)	C29—H29A	0.9900
C14—C15	1.409 (4)	N1—Ni1	1.9552 (19)
C14—H14A	0.9500	N2—Ni1	1.8439 (19)
C15—C16	1.404 (4)	N3—Ni1	1.8721 (19)
C15—H15A	0.9500	Ni1—O2	1.8619 (17)
C16—C17	1.393 (4)	O4—H4W	0.950 (7)
N1—C1—C2	103.65 (19)	N3—C19—C20	105.45 (18)
N1—C1—H1B	111.0	N3—C19—C28	109.73 (19)
C2—C1—H1B	111.0	C20—C19—C28	111.6 (2)
N1—C1—H1A	111.0	N3—C19—H19A	110.0
C2—C1—H1A	111.0	C20—C19—H19A	110.0
H1B—C1—H1A	109.0	C28—C19—H19A	110.0
C1—C2—C3	102.46 (19)	O3—C20—O2	125.6 (2)
C1—C2—H2B	111.3	O3—C20—C19	119.5 (2)
C3—C2—H2B	111.3	O2—C20—C19	114.9 (2)
C1—C2—H2A	111.3	C22—C21—N1	116.21 (19)
C3—C2—H2A	111.3	C22—C21—H21B	108.2
H2B—C2—H2A	109.2	N1—C21—H21B	108.2
C2—C3—C4	104.8 (2)	C22—C21—H21A	108.2
C2—C3—H3B	110.8	N1—C21—H21A	108.2
C4—C3—H3B	110.8	H21B—C21—H21A	107.4
C2—C3—H3A	110.8	C23—C22—C27	120.2 (2)
C4—C3—H3A	110.8	C23—C22—C21	120.1 (2)
H3B—C3—H3A	108.9	C27—C22—C21	119.7 (2)
C5—C4—N1	109.19 (18)	C24—C23—C22	118.8 (3)
C5—C4—C3	112.0 (2)	C24—C23—H23A	120.6
N1—C4—C3	105.49 (18)	C22—C23—H23A	120.6
C5—C4—H4A	110.0	C23—C24—C25	120.1 (3)
N1—C4—H4A	110.0	C23—C24—H24A	119.9
C3—C4—H4A	110.0	C25—C24—H24A	119.9
O1—C5—N2	128.5 (2)	C26—C25—C24	120.6 (3)
O1—C5—C4	118.7 (2)	C26—C25—H25A	119.7
N2—C5—C4	112.71 (19)	C24—C25—H25A	119.7
N2—C6—C7	119.99 (19)	C25—C26—C27	119.9 (3)
N2—C6—C11	120.46 (19)	C25—C26—H26A	120.1
C7—C6—C11	119.4 (2)	C27—C26—H26A	120.1
C8—C7—C6	120.6 (2)	C26—C27—C22	120.3 (3)
C8—C7—H7A	119.7	C26—C27—H27A	119.8
C6—C7—H7A	119.7	C22—C27—H27A	119.8
C7—C8—C9	120.2 (2)	C29—C28—C19	115.6 (2)
C7—C8—H8A	119.9	C29—C28—H28B	108.4
C9—C8—H8A	119.9	C19—C28—H28B	108.4
C10—C9—C8	121.0 (2)	C29—C28—H28A	108.4
C10—C9—H9A	119.5	C19—C28—H28A	108.4
C8—C9—H9A	119.5	H28B—C28—H28A	107.5
C9—C10—C11	120.1 (2)	O4—C29—C28	114.6 (2)
C9—C10—H10A	120.0	O4—C29—H29B	108.6
C11—C10—H10A	120.0	C28—C29—H29B	108.6
C10—C11—C6	118.7 (2)	O4—C29—H29A	108.6
C10—C11—C12	116.5 (2)	C28—C29—H29A	108.6
C6—C11—C12	124.8 (2)	H29B—C29—H29A	107.6
N3—C12—C11	120.6 (2)	C1—N1—C4	103.35 (18)
N3—C12—C13	120.1 (2)	C1—N1—C21	110.15 (18)
C11—C12—C13	119.3 (2)	C4—N1—C21	113.74 (18)
C14—C13—C18	119.2 (2)	C1—N1—Ni1	111.52 (14)
C14—C13—C12	119.5 (2)	C4—N1—Ni1	106.14 (13)
C18—C13—C12	121.1 (2)	C21—N1—Ni1	111.62 (15)
C13—C14—C15	119.8 (3)	C5—N2—C6	121.98 (19)
C13—C14—H14A	120.1	C5—N2—Ni1	115.33 (15)
C15—C14—H14A	120.1	C6—N2—Ni1	122.40 (15)
C16—C15—C14	121.1 (3)	C12—N3—C19	120.82 (19)
C16—C15—H15A	119.5	C12—N3—Ni1	127.19 (16)
C14—C15—H15A	119.5	C19—N3—Ni1	111.98 (14)
C17—C16—C15	119.1 (2)	N2—Ni1—O2	178.29 (8)
C17—C16—H16A	120.5	N2—Ni1—N3	96.12 (8)
C15—C16—H16A	120.5	O2—Ni1—N3	84.94 (8)
C16—C17—C18	120.4 (2)	N2—Ni1—N1	85.11 (8)
C16—C17—H17A	119.8	O2—Ni1—N1	93.88 (8)
C18—C17—H17A	119.8	N3—Ni1—N1	177.24 (9)
C13—C18—C17	120.4 (2)	C20—O2—Ni1	116.03 (16)
C13—C18—H18A	119.8	C29—O4—H4W	108.0 (13)
C17—C18—H18A	119.8
N1—C1—C2—C3	41.8 (2)	C2—C1—N1—C21	−166.68 (19)
C1—C2—C3—C4	−22.6 (2)	C2—C1—N1—Ni1	68.8 (2)
C2—C3—C4—C5	−122.5 (2)	C5—C4—N1—C1	150.08 (18)
C2—C3—C4—N1	−3.8 (2)	C3—C4—N1—C1	29.5 (2)
N1—C4—C5—O1	165.5 (2)	C5—C4—N1—C21	−90.5 (2)
C3—C4—C5—O1	−78.0 (3)	C3—C4—N1—C21	148.95 (19)
N1—C4—C5—N2	−17.5 (2)	C5—C4—N1—Ni1	32.61 (19)
C3—C4—C5—N2	99.0 (2)	C3—C4—N1—Ni1	−87.93 (17)
N2—C6—C7—C8	−175.3 (2)	C22—C21—N1—C1	175.5 (2)
C11—C6—C7—C8	−0.5 (4)	C22—C21—N1—C4	60.1 (3)
C6—C7—C8—C9	−1.0 (4)	C22—C21—N1—Ni1	−60.0 (2)
C7—C8—C9—C10	1.0 (4)	O1—C5—N2—C6	−17.3 (4)
C8—C9—C10—C11	0.5 (5)	C4—C5—N2—C6	166.07 (19)
C9—C10—C11—C6	−1.9 (4)	O1—C5—N2—Ni1	168.8 (2)
C9—C10—C11—C12	178.2 (3)	C4—C5—N2—Ni1	−7.9 (2)
N2—C6—C11—C10	176.8 (2)	C7—C6—N2—C5	−22.5 (3)
C7—C6—C11—C10	1.9 (3)	C11—C6—N2—C5	162.7 (2)
N2—C6—C11—C12	−3.3 (3)	C7—C6—N2—Ni1	151.03 (18)
C7—C6—C11—C12	−178.2 (2)	C11—C6—N2—Ni1	−23.8 (3)
C10—C11—C12—N3	−164.5 (2)	C11—C12—N3—C19	−177.90 (19)
C6—C11—C12—N3	15.6 (3)	C13—C12—N3—C19	3.3 (3)
C10—C11—C12—C13	14.3 (3)	C11—C12—N3—Ni1	1.0 (3)
C6—C11—C12—C13	−165.6 (2)	C13—C12—N3—Ni1	−177.85 (16)
N3—C12—C13—C14	−107.6 (3)	C20—C19—N3—C12	−153.7 (2)
C11—C12—C13—C14	73.5 (3)	C28—C19—N3—C12	85.9 (3)
N3—C12—C13—C18	76.1 (3)	C20—C19—N3—Ni1	27.2 (2)
C11—C12—C13—C18	−102.7 (3)	C28—C19—N3—Ni1	−93.10 (19)
C18—C13—C14—C15	−0.2 (4)	C5—N2—Ni1—O2	76 (3)
C12—C13—C14—C15	−176.5 (2)	C6—N2—Ni1—O2	−98 (3)
C13—C14—C15—C16	0.8 (4)	C5—N2—Ni1—N3	−154.96 (16)
C14—C15—C16—C17	−0.8 (4)	C6—N2—Ni1—N3	31.13 (17)
C15—C16—C17—C18	0.2 (4)	C5—N2—Ni1—N1	22.57 (16)
C14—C13—C18—C17	−0.4 (4)	C6—N2—Ni1—N1	−151.35 (17)
C12—C13—C18—C17	175.9 (2)	C12—N3—Ni1—N2	−20.3 (2)
C16—C17—C18—C13	0.3 (4)	C19—N3—Ni1—N2	158.62 (15)
N3—C19—C20—O3	163.7 (2)	C12—N3—Ni1—O2	158.3 (2)
C28—C19—C20—O3	−77.2 (3)	C19—N3—Ni1—O2	−22.72 (15)
N3—C19—C20—O2	−18.5 (3)	C12—N3—Ni1—N1	−136.9 (18)
C28—C19—C20—O2	100.6 (2)	C19—N3—Ni1—N1	42.1 (19)
N1—C21—C22—C23	81.3 (3)	C1—N1—Ni1—N2	−142.28 (16)
N1—C21—C22—C27	−100.4 (3)	C4—N1—Ni1—N2	−30.41 (14)
C27—C22—C23—C24	2.4 (4)	C21—N1—Ni1—N2	94.03 (16)
C21—C22—C23—C24	−179.4 (2)	C1—N1—Ni1—O2	39.10 (16)
C22—C23—C24—C25	−1.6 (4)	C4—N1—Ni1—O2	150.97 (14)
C23—C24—C25—C26	−0.6 (5)	C21—N1—Ni1—O2	−84.59 (16)
C24—C25—C26—C27	2.0 (5)	C1—N1—Ni1—N3	−25.5 (19)
C25—C26—C27—C22	−1.2 (5)	C4—N1—Ni1—N3	86.4 (18)
C23—C22—C27—C26	−1.0 (4)	C21—N1—Ni1—N3	−149.2 (18)
C21—C22—C27—C26	−179.3 (3)	O3—C20—O2—Ni1	179.3 (2)
N3—C19—C28—C29	179.2 (2)	C19—C20—O2—Ni1	1.6 (3)
C20—C19—C28—C29	62.7 (3)	N2—Ni1—O2—C20	141 (3)
C19—C28—C29—O4	−73.6 (3)	N3—Ni1—O2—C20	12.10 (17)
C2—C1—N1—C4	−44.8 (2)	N1—Ni1—O2—C20	−165.41 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4W···O3	0.95 (1)	1.84 (1)	2.726 (3)	154.(1)
C7—H7A···O1	0.95	2.26	2.837 (3)	118.
C1—H1B···O2	0.99	2.31	2.879 (3)	115.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4W⋯O3	0.950 (7)	1.840 (8)	2.726 (3)	154.0 (9)
C7—H7A⋯O1	0.95	2.26	2.837 (3)	118
C1—H1B⋯O2	0.99	2.31	2.879 (3)	115