(5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetra­azacyclo­tetra­decane-1,8-diacetato)nickel(II) tetra­hydrate

The Ni atom in the title compound, [Ni(C₂₀H₃₈N₄O₄)]·4H₂O, is chelated by four N atoms of the macrocycle and also covalently bonded to two carboxyl­ate groups, in a cis-N₄O₂Ni octa­hedral environment. The mononuclear complex inter­acts with the solvent water mol­ecules to form a three-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.139
• Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H3W2   ..  H4W2    ..       2.04 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O4W    -   H4W1   ...          ?

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.713     0.902
            Tmin(prime) and Tmax expected:      0.839     0.900
            RR(prime) =      0.847
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.84
PLAT417_ALERT_2_C Short Inter D-H..H-D       H3W2   ..  H4W1    ..       2.13 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

(5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-1,8- diacetato)nickel(II) tetrahydrate

Crystal data

[Ni(C20H38N4O4)]·4H2O	F(000) = 1144
Mr = 529.32	Dx = 1.384 Mg m^−3 Dm = 1.380 Mg m^−3 Dm measured by flotation in CH2Cl2/CHCl3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8736 reflections
a = 9.1863 (6) Å	θ = 2.4–28.3°
b = 13.8653 (9) Å	µ = 0.81 mm^−1
c = 19.987 (1) Å	T = 295 K
β = 93.604 (1)°	Prism, blue
V = 2540.7 (3) Å^3	0.21 × 0.18 × 0.13 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	5770 independent reflections
Radiation source: fine-focus sealed tube	5188 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −11→11
Tmin = 0.713, Tmax = 0.902	k = −17→18
21339 measured reflections	l = −25→25

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.15	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 2.6926P] where P = (Fo^2 + 2Fc^2)/3
5770 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.66 e Å^−3
24 restraints	Δρmin = −0.68 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.62450 (4)	0.39195 (2)	0.252575 (17)	0.02529 (12)
O1	0.5296 (2)	0.49268 (15)	0.31572 (11)	0.0365 (5)
O2	0.3917 (3)	0.62511 (18)	0.30452 (15)	0.0532 (7)
O3	0.7595 (2)	0.51133 (15)	0.23475 (10)	0.0338 (5)
O4	0.9252 (3)	0.59946 (16)	0.29356 (14)	0.0494 (6)
O1W	0.5737 (4)	0.5588 (3)	0.45332 (17)	0.0903 (11)
H1W1	0.5665	0.5306	0.4155	0.135*
H1W2	0.4936	0.5863	0.4607	0.135*
O2W	0.8572 (7)	0.5195 (6)	0.5092 (3)	0.172 (2)
H2W1	0.7699	0.5379	0.4994	0.258*
H2W2	0.8564	0.4598	0.5204	0.258*
O3W	0.1271 (9)	0.6186 (5)	0.4048 (4)	0.203 (3)
H3W1	0.0372	0.6274	0.3918	0.304*
H3W2	0.1767	0.6657	0.3878	0.304*
O4W	0.3473 (9)	0.7063 (6)	0.4239 (4)	0.208 (3)
H4W1	0.3245	0.7655	0.4363	0.312*
H4W2	0.3849	0.7163	0.3853	0.312*
N1	0.4302 (3)	0.42481 (19)	0.19563 (13)	0.0340 (5)
N2	0.6992 (3)	0.30603 (18)	0.17542 (12)	0.0332 (5)
H2N	0.6345	0.2614	0.1701	0.040*
N3	0.8168 (3)	0.35176 (16)	0.30689 (12)	0.0284 (5)
N4	0.5097 (3)	0.27361 (18)	0.28789 (12)	0.0319 (5)
H4N	0.5570	0.2243	0.2747	0.038*
C1	0.4461 (3)	0.5513 (2)	0.28269 (17)	0.0365 (7)
C2	0.4100 (4)	0.5285 (2)	0.20906 (17)	0.0426 (8)
H2A	0.3098	0.5465	0.1970	0.051*
H2B	0.4727	0.5660	0.1817	0.051*
C3	0.4356 (4)	0.4015 (3)	0.12262 (17)	0.0448 (8)
H3	0.4234	0.3316	0.1179	0.054*
C4	0.3129 (5)	0.4493 (4)	0.0789 (2)	0.0664 (12)
H4A	0.2203	0.4314	0.0949	0.100*
H4B	0.3178	0.4284	0.0333	0.100*
H4C	0.3238	0.5181	0.0811	0.100*
C5	0.5847 (4)	0.4269 (3)	0.09825 (17)	0.0475 (8)
H5A	0.6192	0.4845	0.1218	0.057*
H5B	0.5718	0.4433	0.0511	0.057*
C6	0.7056 (4)	0.3499 (3)	0.10642 (16)	0.0422 (8)
C7	0.8517 (5)	0.3991 (3)	0.0974 (2)	0.0572 (10)
H7A	0.9287	0.3523	0.1023	0.086*
H7B	0.8676	0.4484	0.1308	0.086*
H7C	0.8508	0.4275	0.0536	0.086*
C8	0.6802 (5)	0.2698 (3)	0.05386 (19)	0.0658 (12)
H8A	0.7561	0.2224	0.0597	0.099*
H8B	0.6813	0.2972	0.0098	0.099*
H8C	0.5875	0.2399	0.0592	0.099*
C9	0.8319 (3)	0.2544 (2)	0.20329 (17)	0.0386 (7)
H9A	0.8944	0.2395	0.1673	0.046*
H9B	0.8035	0.1941	0.2233	0.046*
C10	0.9159 (3)	0.3152 (2)	0.25579 (16)	0.0355 (7)
H10A	0.9930	0.2768	0.2778	0.043*
H10B	0.9606	0.3694	0.2342	0.043*
C11	0.8761 (3)	0.4438 (2)	0.33424 (16)	0.0344 (6)
H11A	0.9796	0.4367	0.3458	0.041*
H11B	0.8285	0.4601	0.3747	0.041*
C12	0.8517 (3)	0.5244 (2)	0.28302 (16)	0.0336 (6)
C13	0.7914 (3)	0.2769 (2)	0.35950 (16)	0.0357 (7)
H13	0.7750	0.2153	0.3362	0.043*
C14	0.9218 (4)	0.2630 (3)	0.4099 (2)	0.0555 (10)
H14A	1.0071	0.2488	0.3863	0.083*
H14B	0.9025	0.2106	0.4394	0.083*
H14C	0.9376	0.3211	0.4355	0.083*
C15	0.6527 (4)	0.3001 (2)	0.39488 (15)	0.0391 (7)
H15A	0.6441	0.3697	0.3977	0.047*
H15B	0.6648	0.2757	0.4404	0.047*
C16	0.5078 (4)	0.2603 (2)	0.36284 (16)	0.0385 (7)
C17	0.3832 (4)	0.3154 (3)	0.3922 (2)	0.0545 (10)
H17A	0.2918	0.2919	0.3727	0.082*
H17B	0.3924	0.3828	0.3824	0.082*
H17C	0.3871	0.3061	0.4398	0.082*
C18	0.4962 (5)	0.1517 (3)	0.3774 (2)	0.0574 (10)
H18A	0.4058	0.1274	0.3574	0.086*
H18B	0.4995	0.1416	0.4250	0.086*
H18C	0.5761	0.1185	0.3589	0.086*
C19	0.3675 (3)	0.2691 (2)	0.24787 (18)	0.0417 (7)
H19A	0.2957	0.2380	0.2742	0.050*
H19B	0.3784	0.2304	0.2081	0.050*
C20	0.3139 (3)	0.3692 (2)	0.22733 (18)	0.0401 (7)
H20A	0.2294	0.3636	0.1959	0.048*
H20B	0.2845	0.4036	0.2665	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.02330 (19)	0.02274 (19)	0.0294 (2)	0.00150 (13)	−0.00140 (13)	−0.00099 (13)
O1	0.0401 (12)	0.0320 (11)	0.0373 (11)	0.0033 (9)	0.0020 (9)	−0.0038 (9)
O2	0.0446 (14)	0.0378 (13)	0.0772 (18)	0.0109 (11)	0.0032 (13)	−0.0157 (12)
O3	0.0358 (11)	0.0272 (10)	0.0380 (11)	−0.0006 (8)	−0.0016 (9)	0.0041 (8)
O4	0.0484 (14)	0.0280 (12)	0.0697 (17)	−0.0128 (10)	−0.0120 (12)	0.0095 (11)
O1W	0.111 (3)	0.092 (3)	0.066 (2)	−0.013 (2)	−0.0014 (19)	−0.0151 (19)
O2W	0.132 (4)	0.227 (6)	0.157 (5)	0.004 (4)	0.003 (4)	0.004 (5)
O3W	0.236 (6)	0.152 (5)	0.203 (6)	0.004 (5)	−0.122 (5)	0.003 (4)
O4W	0.222 (6)	0.222 (7)	0.182 (6)	0.035 (6)	0.023 (5)	−0.020 (5)
N1	0.0312 (13)	0.0329 (13)	0.0374 (13)	0.0049 (10)	−0.0040 (10)	−0.0031 (11)
N2	0.0319 (13)	0.0320 (13)	0.0352 (13)	0.0026 (10)	−0.0022 (10)	−0.0057 (10)
N3	0.0274 (12)	0.0222 (11)	0.0350 (12)	−0.0015 (9)	−0.0031 (10)	0.0031 (9)
N4	0.0302 (13)	0.0268 (12)	0.0385 (13)	−0.0011 (10)	0.0008 (10)	−0.0027 (10)
C1	0.0277 (15)	0.0303 (15)	0.0518 (18)	0.0012 (12)	0.0038 (13)	−0.0053 (13)
C2	0.0421 (18)	0.0343 (17)	0.0501 (19)	0.0124 (14)	−0.0062 (15)	0.0021 (14)
C3	0.0460 (19)	0.049 (2)	0.0372 (17)	0.0088 (15)	−0.0120 (14)	−0.0052 (14)
C4	0.059 (3)	0.088 (3)	0.049 (2)	0.018 (2)	−0.0245 (19)	−0.001 (2)
C5	0.054 (2)	0.054 (2)	0.0345 (17)	0.0109 (17)	−0.0008 (15)	0.0039 (15)
C6	0.0459 (19)	0.050 (2)	0.0309 (15)	0.0072 (15)	0.0017 (13)	−0.0061 (14)
C7	0.057 (2)	0.067 (3)	0.049 (2)	0.006 (2)	0.0142 (18)	0.0071 (19)
C8	0.077 (3)	0.078 (3)	0.041 (2)	0.013 (2)	−0.0058 (19)	−0.024 (2)
C9	0.0360 (17)	0.0322 (16)	0.0476 (18)	0.0086 (13)	0.0032 (13)	−0.0037 (13)
C10	0.0222 (14)	0.0345 (16)	0.0492 (18)	0.0062 (11)	−0.0027 (12)	0.0042 (13)
C11	0.0357 (16)	0.0257 (14)	0.0400 (16)	−0.0062 (12)	−0.0116 (13)	0.0006 (12)
C12	0.0323 (15)	0.0262 (14)	0.0422 (16)	−0.0015 (11)	0.0013 (12)	0.0019 (12)
C13	0.0385 (17)	0.0272 (15)	0.0402 (16)	−0.0022 (12)	−0.0073 (13)	0.0083 (12)
C14	0.055 (2)	0.053 (2)	0.056 (2)	−0.0039 (18)	−0.0208 (18)	0.0217 (18)
C15	0.0488 (19)	0.0356 (16)	0.0330 (15)	−0.0061 (14)	0.0024 (13)	0.0045 (13)
C16	0.0393 (17)	0.0355 (16)	0.0415 (17)	−0.0095 (13)	0.0087 (13)	0.0035 (13)
C17	0.051 (2)	0.061 (2)	0.054 (2)	−0.0097 (18)	0.0183 (17)	−0.0032 (18)
C18	0.068 (3)	0.041 (2)	0.064 (2)	−0.0178 (18)	0.008 (2)	0.0137 (18)
C19	0.0309 (16)	0.0359 (17)	0.057 (2)	−0.0066 (13)	−0.0034 (14)	−0.0073 (15)
C20	0.0270 (15)	0.0405 (17)	0.0520 (19)	0.0014 (13)	−0.0053 (14)	−0.0054 (15)

Geometric parameters (Å, º)

Ni1—N1	2.106 (2)	C5—H5A	0.97
Ni1—N2	2.098 (2)	C5—H5B	0.97
Ni1—N3	2.090 (2)	C6—C7	1.526 (5)
Ni1—N4	2.097 (2)	C6—C8	1.536 (5)
Ni1—O1	2.108 (2)	C7—H7A	0.96
Ni1—O3	2.112 (2)	C7—H7B	0.96
O1—C1	1.273 (4)	C7—H7C	0.96
O2—C1	1.231 (4)	C8—H8A	0.96
O3—C12	1.257 (4)	C8—H8B	0.96
O4—C12	1.251 (4)	C8—H8C	0.96
O1W—H1W1	0.85	C9—C10	1.518 (4)
O1W—H1W2	0.85	C9—H9A	0.97
O2W—H2W1	0.85	C9—H9B	0.97
O2W—H2W2	0.86	C10—H10A	0.97
O3W—H3W1	0.86	C10—H10B	0.97
O3W—H3W2	0.88	C11—C12	1.523 (4)
O4W—H4W1	0.89	C11—H11A	0.97
O4W—H4W2	0.88	C11—H11B	0.97
N1—C2	1.477 (4)	C13—C14	1.527 (4)
N1—C20	1.490 (4)	C13—C15	1.530 (5)
N1—C3	1.498 (4)	C13—H13	0.98
N2—C9	1.492 (4)	C14—H14A	0.96
N2—C6	1.512 (4)	C14—H14B	0.96
N2—H2N	0.86	C14—H14C	0.96
N3—C11	1.478 (4)	C15—C16	1.543 (5)
N3—C10	1.499 (4)	C15—H15A	0.97
N3—C13	1.506 (4)	C15—H15B	0.97
N4—C19	1.490 (4)	C16—C17	1.523 (5)
N4—C16	1.511 (4)	C16—C18	1.538 (5)
N4—H4N	0.86	C17—H17A	0.96
C1—C2	1.521 (5)	C17—H17B	0.96
C2—H2A	0.97	C17—H17C	0.96
C2—H2B	0.97	C18—H18A	0.96
C3—C5	1.524 (5)	C18—H18B	0.96
C3—C4	1.533 (5)	C18—H18C	0.96
C3—H3	0.98	C19—C20	1.521 (5)
C4—H4A	0.96	C19—H19A	0.97
C4—H4B	0.96	C19—H19B	0.97
C4—H4C	0.96	C20—H20A	0.97
C5—C6	1.542 (5)	C20—H20B	0.97
N1—Ni1—N2	91.8 (1)	H7A—C7—H7B	109.5
N1—Ni1—N3	176.9 (1)	C6—C7—H7C	109.5
N1—Ni1—N4	85.6 (1)	H7A—C7—H7C	109.5
N1—Ni1—O1	79.1 (1)	H7B—C7—H7C	109.5
N1—Ni1—O3	103.1 (1)	C6—C8—H8A	109.5
N2—Ni1—N3	85.7 (1)	C6—C8—H8B	109.5
N2—Ni1—N4	89.9 (1)	H8A—C8—H8B	109.5
N2—Ni1—O1	169.5 (1)	C6—C8—H8C	109.5
N2—Ni1—O3	95.7 (1)	H8A—C8—H8C	109.5
N3—Ni1—N4	92.5 (1)	H8B—C8—H8C	109.5
N3—Ni1—O1	103.5 (1)	N2—C9—C10	111.1 (2)
N3—Ni1—O3	79.1 (1)	N2—C9—H9A	109.4
N4—Ni1—O1	94.7 (1)	C10—C9—H9A	109.4
N4—Ni1—O3	169.5 (1)	N2—C9—H9B	109.4
O1—Ni1—O3	81.4 (1)	C10—C9—H9B	109.4
C1—O1—Ni1	111.77 (19)	H9A—C9—H9B	108.0
C12—O3—Ni1	111.00 (18)	N3—C10—C9	110.8 (2)
H1W1—O1W—H1W2	110.0	N3—C10—H10A	109.5
H2W1—O2W—H2W2	109.0	C9—C10—H10A	109.5
H3W1—O3W—H3W2	106.9	N3—C10—H10B	109.5
H4W1—O4W—H4W2	102.3	C9—C10—H10B	109.5
C2—N1—C20	109.0 (3)	H10A—C10—H10B	108.1
C2—N1—C3	113.5 (3)	N3—C11—C12	110.5 (2)
C20—N1—C3	111.8 (3)	N3—C11—H11A	109.6
C2—N1—Ni1	102.96 (19)	C12—C11—H11A	109.6
C20—N1—Ni1	105.32 (19)	N3—C11—H11B	109.6
C3—N1—Ni1	113.62 (19)	C12—C11—H11B	109.6
C9—N2—C6	117.1 (2)	H11A—C11—H11B	108.1
C9—N2—Ni1	107.18 (18)	O4—C12—O3	125.5 (3)
C6—N2—Ni1	118.40 (19)	O4—C12—C11	116.3 (3)
C9—N2—H2N	104.1	O3—C12—C11	118.3 (3)
C6—N2—H2N	104.1	N3—C13—C14	113.4 (3)
Ni1—N2—H2N	104.1	N3—C13—C15	110.3 (2)
C11—N3—C10	108.6 (2)	C14—C13—C15	111.3 (3)
C11—N3—C13	114.0 (2)	N3—C13—H13	107.2
C10—N3—C13	111.7 (2)	C14—C13—H13	107.2
C11—N3—Ni1	103.98 (17)	C15—C13—H13	107.2
C10—N3—Ni1	105.42 (17)	C13—C14—H14A	109.5
C13—N3—Ni1	112.57 (18)	C13—C14—H14B	109.5
C19—N4—C16	117.6 (2)	H14A—C14—H14B	109.5
C19—N4—Ni1	107.16 (19)	C13—C14—H14C	109.5
C16—N4—Ni1	117.86 (18)	H14A—C14—H14C	109.5
C19—N4—H4N	104.1	H14B—C14—H14C	109.5
C16—N4—H4N	104.1	C13—C15—C16	117.0 (3)
Ni1—N4—H4N	104.1	C13—C15—H15A	108.0
O2—C1—O1	126.3 (3)	C16—C15—H15A	108.0
O2—C1—C2	116.5 (3)	C13—C15—H15B	108.0
O1—C1—C2	117.2 (3)	C16—C15—H15B	108.0
N1—C2—C1	110.8 (3)	H15A—C15—H15B	107.3
N1—C2—H2A	109.5	N4—C16—C17	112.1 (3)
C1—C2—H2A	109.5	N4—C16—C18	108.2 (3)
N1—C2—H2B	109.5	C17—C16—C18	110.8 (3)
C1—C2—H2B	109.5	N4—C16—C15	107.7 (2)
H2A—C2—H2B	108.1	C17—C16—C15	108.1 (3)
N1—C3—C5	110.3 (3)	C18—C16—C15	109.9 (3)
N1—C3—C4	113.2 (3)	C16—C17—H17A	109.5
C5—C3—C4	111.2 (3)	C16—C17—H17B	109.5
N1—C3—H3	107.3	H17A—C17—H17B	109.5
C5—C3—H3	107.3	C16—C17—H17C	109.5
C4—C3—H3	107.3	H17A—C17—H17C	109.5
C3—C4—H4A	109.5	H17B—C17—H17C	109.5
C3—C4—H4B	109.5	C16—C18—H18A	109.5
H4A—C4—H4B	109.5	C16—C18—H18B	109.5
C3—C4—H4C	109.5	H18A—C18—H18B	109.5
H4A—C4—H4C	109.5	C16—C18—H18C	109.5
H4B—C4—H4C	109.5	H18A—C18—H18C	109.5
C3—C5—C6	117.5 (3)	H18B—C18—H18C	109.5
C3—C5—H5A	107.9	N4—C19—C20	111.4 (3)
C6—C5—H5A	107.9	N4—C19—H19A	109.4
C3—C5—H5B	107.9	C20—C19—H19A	109.4
C6—C5—H5B	107.9	N4—C19—H19B	109.4
H5A—C5—H5B	107.2	C20—C19—H19B	109.4
N2—C6—C7	111.8 (3)	H19A—C19—H19B	108.0
N2—C6—C8	108.7 (3)	N1—C20—C19	111.0 (3)
C7—C6—C8	109.8 (3)	N1—C20—H20A	109.4
N2—C6—C5	107.8 (2)	C19—C20—H20A	109.4
C7—C6—C5	108.1 (3)	N1—C20—H20B	109.4
C8—C6—C5	110.5 (3)	C19—C20—H20B	109.4
C6—C7—H7A	109.5	H20A—C20—H20B	108.0
C6—C7—H7B	109.5
N3—Ni1—O1—C1	154.5 (2)	C3—N1—C2—C1	−164.7 (3)
N4—Ni1—O1—C1	−111.8 (2)	Ni1—N1—C2—C1	−41.4 (3)
N2—Ni1—O1—C1	3.4 (6)	O2—C1—C2—N1	−157.7 (3)
N1—Ni1—O1—C1	−27.2 (2)	O1—C1—C2—N1	22.5 (4)
O3—Ni1—O1—C1	78.0 (2)	C2—N1—C3—C5	77.9 (3)
N3—Ni1—O3—C12	−29.3 (2)	C20—N1—C3—C5	−158.3 (3)
N4—Ni1—O3—C12	7.6 (6)	Ni1—N1—C3—C5	−39.3 (3)
N2—Ni1—O3—C12	−113.8 (2)	C2—N1—C3—C4	−47.3 (4)
N1—Ni1—O3—C12	153.1 (2)	C20—N1—C3—C4	76.4 (4)
O1—Ni1—O3—C12	76.4 (2)	Ni1—N1—C3—C4	−164.6 (3)
N4—Ni1—N1—C2	131.7 (2)	N1—C3—C5—C6	86.8 (4)
N2—Ni1—N1—C2	−138.6 (2)	C4—C3—C5—C6	−146.8 (3)
O1—Ni1—N1—C2	36.1 (2)	C9—N2—C6—C7	−41.8 (4)
O3—Ni1—N1—C2	−42.3 (2)	Ni1—N2—C6—C7	89.0 (3)
N4—Ni1—N1—C20	17.58 (19)	C9—N2—C6—C8	79.6 (4)
N2—Ni1—N1—C20	107.3 (2)	Ni1—N2—C6—C8	−149.5 (3)
O1—Ni1—N1—C20	−78.02 (19)	C9—N2—C6—C5	−160.5 (3)
O3—Ni1—N1—C20	−156.47 (18)	Ni1—N2—C6—C5	−29.7 (3)
N4—Ni1—N1—C3	−105.1 (2)	C3—C5—C6—N2	−43.4 (4)
N2—Ni1—N1—C3	−15.3 (2)	C3—C5—C6—C7	−164.5 (3)
O1—Ni1—N1—C3	159.3 (2)	C3—C5—C6—C8	75.3 (4)
O3—Ni1—N1—C3	80.9 (2)	C6—N2—C9—C10	103.7 (3)
N3—Ni1—N2—C9	7.5 (2)	Ni1—N2—C9—C10	−32.2 (3)
N4—Ni1—N2—C9	−85.0 (2)	C11—N3—C10—C9	−151.8 (2)
N1—Ni1—N2—C9	−170.6 (2)	C13—N3—C10—C9	81.7 (3)
O1—Ni1—N2—C9	159.4 (5)	Ni1—N3—C10—C9	−40.9 (3)
O3—Ni1—N2—C9	86.1 (2)	N2—C9—C10—N3	50.7 (3)
N3—Ni1—N2—C6	−127.7 (2)	C10—N3—C11—C12	73.5 (3)
N4—Ni1—N2—C6	139.8 (2)	C13—N3—C11—C12	−161.3 (2)
N1—Ni1—N2—C6	54.2 (2)	Ni1—N3—C11—C12	−38.3 (3)
O1—Ni1—N2—C6	24.2 (6)	Ni1—O3—C12—O4	−164.3 (3)
O3—Ni1—N2—C6	−49.1 (2)	Ni1—O3—C12—C11	14.6 (3)
N4—Ni1—N3—C11	−138.13 (18)	N3—C11—C12—O4	−164.0 (3)
N2—Ni1—N3—C11	132.19 (19)	N3—C11—C12—O3	17.0 (4)
O1—Ni1—N3—C11	−42.73 (19)	C11—N3—C13—C14	−48.8 (4)
O3—Ni1—N3—C11	35.59 (18)	C10—N3—C13—C14	74.7 (3)
N4—Ni1—N3—C10	107.73 (18)	Ni1—N3—C13—C14	−166.9 (2)
N2—Ni1—N3—C10	18.05 (18)	C11—N3—C13—C15	76.8 (3)
O1—Ni1—N3—C10	−156.88 (17)	C10—N3—C13—C15	−159.7 (2)
O3—Ni1—N3—C10	−78.56 (18)	Ni1—N3—C13—C15	−41.3 (3)
N4—Ni1—N3—C13	−14.3 (2)	N3—C13—C15—C16	87.7 (3)
N2—Ni1—N3—C13	−104.0 (2)	C14—C13—C15—C16	−145.5 (3)
O1—Ni1—N3—C13	81.1 (2)	C19—N4—C16—C17	−43.0 (4)
O3—Ni1—N3—C13	159.4 (2)	Ni1—N4—C16—C17	87.7 (3)
N3—Ni1—N4—C19	−169.62 (19)	C19—N4—C16—C18	79.5 (4)
N2—Ni1—N4—C19	−83.9 (2)	Ni1—N4—C16—C18	−149.8 (2)
N1—Ni1—N4—C19	7.90 (19)	C19—N4—C16—C15	−161.7 (3)
O1—Ni1—N4—C19	86.61 (19)	Ni1—N4—C16—C15	−31.0 (3)
O3—Ni1—N4—C19	154.2 (4)	C13—C15—C16—N4	−41.8 (4)
N3—Ni1—N4—C16	55.1 (2)	C13—C15—C16—C17	−163.0 (3)
N2—Ni1—N4—C16	140.8 (2)	C13—C15—C16—C18	75.9 (4)
N1—Ni1—N4—C16	−127.4 (2)	C16—N4—C19—C20	103.1 (3)
O1—Ni1—N4—C16	−48.7 (2)	Ni1—N4—C19—C20	−32.4 (3)
O3—Ni1—N4—C16	18.9 (6)	C2—N1—C20—C19	−150.1 (3)
Ni1—O1—C1—O2	−169.6 (3)	C3—N1—C20—C19	83.6 (3)
Ni1—O1—C1—C2	10.2 (3)	Ni1—N1—C20—C19	−40.3 (3)
C20—N1—C2—C1	70.1 (3)	N4—C19—C20—N1	50.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O4^i	0.86	2.43	3.160 (4)	143
N4—H4N···O4^i	0.86	2.22	2.993 (3)	150
O1W—H1W1···O1	0.85	2.07	2.903 (4)	167
O1W—H1W2···O4W	0.85	2.24	2.949 (9)	142
O2W—H2W1···O1W	0.85	1.99	2.822 (7)	164
O2W—H2W2···O3W^ii	0.86	1.85	2.57 (1)	141
O3W—H3W1···O4^iii	0.86	2.19	2.817 (6)	129
O3W—H3W2···O4W	0.88	1.78	2.37 (1)	123
O4W—H4W2···O2	0.88	2.05	2.693 (8)	129

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z.