Aqua­bis(1,5-di­methyl-2-phenyl-4-{[(E)-4-pyridyl­methyl­ene-κN]­amino}pyrazolidin-3-one)­dinitratonickel(II)

In the title compound, [Ni(NO₃)₂(C₁₇H₁₆N₄O)₂(H₂O)], the six-coordinate Ni atom is bound by two trans 4-amino­antipyrine ligands. Such compounds possess antimicrobial properties. The crystal packing is stabilized by intermolecular hydrogen bonds and non-classical C—H...O hydrogen bonds, which generate a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.094
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Ni     -   O3       =      10.46 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Ni     -   O4       =      37.49 su

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   N9       =       5.71 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni     -   O6       =       5.67 su
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         O4
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         N9
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        N10
PLAT725_ALERT_1_C D-H     Calc     0.95927, Rep     0.94000, Dev.        0.02 Ang.
              C10  -H10C    1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.81(3), Rep   0.811(10) ......       3.00 su-Rat
              O9   -H9A     1.555   1.555
PLAT745_ALERT_1_C D-H     Calc     0.81(3), Rep     0.81000 ......    Missing su
              O9   -H9A     1.555   1.555
PLAT745_ALERT_1_C D-H     Calc     0.82(2), Rep     0.82000 ......    Missing su
              O9   -H9B     1.555   1.555
PLAT746_ALERT_1_C H...A   Calc     1.84(3), Rep     1.84000 ......    Missing su
              H9A  -O2      1.555   2.655
PLAT746_ALERT_1_C H...A   Calc     1.87(2), Rep     1.87000 ......    Missing su
              H9B  -O1      1.555   2.566

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

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

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Computing details

Data collection: SXSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Aquabis(1,5-dimethyl-2-phenyl-4-{[(E)-4-pyridylmethylene- κN]amino}pyrazolidin-3-one)dinitratonickel(II)

Crystal data

[Ni(NO3)2(C17H16N4O)2(NO3)2(H2O)]	Z = 2
Mr = 785.42	F(000) = 816
Triclinic, P1	Dx = 1.443 Mg m^−3
a = 10.097 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.977 (2) Å	Cell parameters from 28 reflections
c = 14.860 (2) Å	θ = 2.8–14.6°
α = 88.86 (1)°	µ = 0.61 mm^−1
β = 75.41 (1)°	T = 296 K
γ = 73.86 (1)°	Block, green
V = 1807.3 (5) Å^3	0.52 × 0.50 × 0.16 mm

Data collection

Siemens P4 diffractometer	4930 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.012
Graphite monochromator	θmax = 25.3°, θmin = 1.4°
ω scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = −14→15
Tmin = 0.732, Tmax = 0.908	l = −17→17
7176 measured reflections	3 standard reflections every 97 reflections
6540 independent reflections	intensity decay: 2.4%

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)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0539P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
6540 reflections	Δρmax = 0.42 e Å^−3
500 parameters	Δρmin = −0.30 e Å^−3
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (5)

Special details

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.

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

	x	y	z	Uiso*/Ueq
Ni	0.39893 (3)	0.21672 (2)	0.23919 (2)	0.03265 (11)
O1	−0.0322 (2)	0.80716 (15)	0.61519 (12)	0.0559 (5)
O2	0.9364 (2)	−0.34901 (16)	−0.14942 (13)	0.0597 (5)
O3	0.3665 (2)	0.18154 (15)	0.37970 (13)	0.0537 (5)
O4	0.5556 (2)	0.22702 (16)	0.32389 (16)	0.0683 (6)
O5	0.4936 (3)	0.1973 (3)	0.47117 (17)	0.1102 (10)
O6	0.44602 (19)	0.26009 (15)	0.10393 (12)	0.0501 (5)
O7	0.6117 (2)	0.28237 (19)	−0.00933 (15)	0.0837 (8)
O8	0.6468 (3)	0.2606 (2)	0.1273 (2)	0.0980 (9)
O9	0.22006 (18)	0.18917 (14)	0.22241 (13)	0.0362 (4)
N1	0.2993 (2)	0.37707 (15)	0.28587 (13)	0.0355 (5)
N2	0.2006 (2)	0.74980 (15)	0.42712 (13)	0.0383 (5)
N3	0.1737 (2)	0.98261 (15)	0.55898 (14)	0.0407 (5)
N4	0.0635 (2)	0.94957 (16)	0.61731 (13)	0.0411 (5)
N5	0.5139 (2)	0.05842 (15)	0.19321 (14)	0.0365 (5)
N6	0.9103 (2)	−0.27563 (16)	0.05646 (14)	0.0398 (5)
N7	1.2171 (2)	−0.48092 (16)	−0.05934 (14)	0.0432 (5)
N8	1.1478 (2)	−0.46009 (16)	−0.13035 (14)	0.0437 (5)
N9	0.4740 (3)	0.20195 (18)	0.39484 (16)	0.0522 (6)
N10	0.5725 (3)	0.26739 (17)	0.07371 (16)	0.0480 (6)
C1	0.1623 (3)	0.41141 (19)	0.33369 (18)	0.0434 (6)
H1	0.1048	0.3659	0.3364	0.052*
C2	0.1032 (3)	0.5113 (2)	0.37892 (18)	0.0440 (6)
H2	0.0072	0.5325	0.4107	0.053*
C3	0.1867 (3)	0.58083 (18)	0.37736 (16)	0.0370 (6)
C4	0.3259 (3)	0.54678 (19)	0.32414 (18)	0.0438 (6)
H4	0.3844	0.5920	0.3177	0.053*
C5	0.3779 (3)	0.44577 (19)	0.28055 (18)	0.0432 (6)
H5	0.4724	0.4242	0.2457	0.052*
C6	0.1303 (3)	0.68107 (19)	0.43576 (17)	0.0403 (6)
H6	0.0425	0.6944	0.4794	0.048*
C7	0.0539 (3)	0.85678 (19)	0.57731 (17)	0.0386 (6)
C8	0.1578 (3)	0.83771 (18)	0.49016 (16)	0.0349 (5)
C9	0.2268 (3)	0.91701 (19)	0.48172 (17)	0.0380 (6)
C10	0.3379 (3)	0.9348 (2)	0.40094 (18)	0.0524 (7)
H10A	0.2965	0.9952	0.3687	0.063*
H10B	0.3755	0.8719	0.3594	0.063*
H10C	0.4134	0.9489	0.4225	0.063*
C11	0.2007 (3)	1.0826 (2)	0.5768 (2)	0.0565 (8)
H11A	0.2733	1.0950	0.5256	0.068*
H11B	0.2321	1.0792	0.6329	0.068*
H11C	0.1146	1.1403	0.5838	0.068*
C12	0.0115 (3)	0.97854 (19)	0.71523 (16)	0.0366 (6)
C13	−0.0896 (3)	1.0756 (2)	0.74506 (19)	0.0507 (7)
H13	−0.1198	1.1240	0.7024	0.061*
C14	−0.1453 (3)	1.0994 (3)	0.8397 (2)	0.0686 (9)
H14	−0.2124	1.1650	0.8610	0.082*
C15	−0.1026 (4)	1.0277 (4)	0.9023 (2)	0.0773 (11)
H15	−0.1419	1.0441	0.9657	0.093*
C16	−0.0013 (4)	0.9308 (3)	0.8717 (2)	0.0703 (10)
H16	0.0279	0.8821	0.9145	0.084*
C17	0.0566 (3)	0.9065 (2)	0.7775 (2)	0.0501 (7)
H17	0.1256	0.8418	0.7565	0.060*
C18	0.4715 (3)	0.0029 (2)	0.13734 (19)	0.0475 (7)
H18	0.3791	0.0293	0.1307	0.057*
C19	0.5566 (3)	−0.0916 (2)	0.08868 (19)	0.0500 (7)
H19	0.5214	−0.1271	0.0504	0.060*
C20	0.6944 (3)	−0.13333 (18)	0.09696 (16)	0.0375 (6)
C21	0.7367 (3)	−0.0797 (2)	0.15899 (19)	0.0490 (7)
H21	0.8262	−0.1070	0.1702	0.059*
C22	0.6451 (3)	0.0147 (2)	0.20412 (19)	0.0473 (7)
H22	0.6763	0.0502	0.2447	0.057*
C23	0.7931 (3)	−0.22666 (19)	0.03797 (17)	0.0406 (6)
H23	0.7697	−0.2501	−0.0132	0.049*
C24	1.0198 (3)	−0.38176 (19)	−0.09916 (17)	0.0408 (6)
C25	1.0120 (3)	−0.35584 (18)	−0.00481 (17)	0.0361 (5)
C26	1.1347 (3)	−0.4184 (2)	0.01558 (17)	0.0403 (6)
C27	1.1749 (3)	−0.4227 (2)	0.10564 (19)	0.0556 (7)
H27A	1.1744	−0.4910	0.1315	0.067*
H27B	1.1075	−0.3664	0.1482	0.067*
H27C	1.2685	−0.4135	0.0953	0.067*
C28	1.3593 (3)	−0.5513 (2)	−0.0726 (2)	0.0578 (8)
H28A	1.4271	−0.5111	−0.0934	0.069*
H28B	1.3752	−0.6075	−0.1185	0.069*
H28C	1.3704	−0.5822	−0.0148	0.069*
C29	1.2146 (3)	−0.4958 (2)	−0.22557 (17)	0.0422 (6)
C30	1.2530 (3)	−0.4228 (2)	−0.2882 (2)	0.0577 (8)
H30	1.2394	−0.3524	−0.2678	0.069*
C31	1.3114 (4)	−0.4545 (3)	−0.3809 (2)	0.0759 (10)
H31	1.3369	−0.4053	−0.4232	0.091*
C32	1.3321 (4)	−0.5577 (3)	−0.4110 (2)	0.0788 (11)
H32	1.3709	−0.5786	−0.4738	0.095*
C33	1.2957 (4)	−0.6301 (3)	−0.3489 (2)	0.0796 (11)
H33	1.3120	−0.7009	−0.3694	0.096*
C34	1.2348 (3)	−0.5994 (2)	−0.2556 (2)	0.0628 (8)
H34	1.2077	−0.6487	−0.2138	0.075*
H9A	0.175 (3)	0.232 (2)	0.1935 (19)	0.069 (11)*
H9B	0.164 (3)	0.177 (3)	0.2686 (14)	0.074 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.03375 (18)	0.02775 (17)	0.03507 (18)	−0.00897 (12)	−0.00569 (13)	−0.00348 (12)
O1	0.0636 (12)	0.0547 (11)	0.0489 (11)	−0.0377 (10)	0.0110 (9)	−0.0155 (9)
O2	0.0564 (12)	0.0585 (12)	0.0496 (12)	0.0139 (10)	−0.0205 (10)	−0.0068 (9)
O3	0.0662 (13)	0.0472 (11)	0.0540 (12)	−0.0207 (10)	−0.0221 (10)	0.0090 (9)
O4	0.0587 (13)	0.0513 (12)	0.0859 (17)	−0.0167 (10)	−0.0005 (12)	−0.0082 (11)
O5	0.116 (2)	0.147 (3)	0.0616 (16)	0.0057 (19)	−0.0569 (16)	−0.0179 (16)
O6	0.0426 (11)	0.0548 (11)	0.0450 (11)	−0.0131 (9)	0.0019 (9)	0.0038 (9)
O7	0.0737 (16)	0.0930 (18)	0.0561 (14)	−0.0145 (13)	0.0227 (12)	0.0143 (12)
O8	0.0881 (19)	0.117 (2)	0.109 (2)	−0.0341 (17)	−0.0552 (17)	0.0112 (17)
O9	0.0326 (10)	0.0356 (10)	0.0388 (11)	−0.0089 (8)	−0.0067 (9)	−0.0022 (8)
N1	0.0404 (12)	0.0288 (10)	0.0362 (11)	−0.0096 (9)	−0.0075 (9)	−0.0024 (8)
N2	0.0460 (12)	0.0298 (11)	0.0358 (11)	−0.0092 (9)	−0.0062 (9)	−0.0027 (8)
N3	0.0501 (13)	0.0304 (11)	0.0402 (12)	−0.0191 (10)	−0.0004 (10)	−0.0034 (9)
N4	0.0496 (13)	0.0378 (11)	0.0355 (11)	−0.0217 (10)	0.0009 (10)	−0.0075 (9)
N5	0.0320 (11)	0.0345 (11)	0.0416 (12)	−0.0079 (9)	−0.0080 (9)	−0.0058 (9)
N6	0.0403 (12)	0.0318 (11)	0.0408 (12)	−0.0072 (9)	−0.0016 (10)	−0.0017 (9)
N7	0.0366 (12)	0.0429 (12)	0.0445 (13)	−0.0007 (10)	−0.0123 (10)	0.0045 (10)
N8	0.0418 (12)	0.0402 (12)	0.0375 (12)	0.0065 (10)	−0.0091 (10)	−0.0039 (9)
N9	0.0624 (16)	0.0463 (14)	0.0412 (14)	−0.0040 (12)	−0.0129 (13)	−0.0089 (11)
N10	0.0503 (14)	0.0398 (12)	0.0453 (14)	−0.0105 (11)	0.0010 (12)	−0.0003 (10)
C1	0.0439 (15)	0.0362 (14)	0.0485 (16)	−0.0167 (12)	−0.0020 (12)	−0.0089 (11)
C2	0.0409 (15)	0.0397 (14)	0.0442 (15)	−0.0094 (12)	0.0007 (12)	−0.0087 (11)
C3	0.0481 (15)	0.0272 (12)	0.0339 (13)	−0.0097 (11)	−0.0080 (11)	−0.0021 (10)
C4	0.0444 (15)	0.0331 (13)	0.0514 (16)	−0.0158 (12)	−0.0016 (12)	−0.0055 (11)
C5	0.0400 (14)	0.0343 (14)	0.0485 (16)	−0.0111 (11)	0.0019 (12)	−0.0062 (11)
C6	0.0424 (14)	0.0329 (13)	0.0410 (14)	−0.0100 (11)	−0.0026 (11)	−0.0056 (11)
C7	0.0438 (14)	0.0335 (13)	0.0387 (14)	−0.0156 (11)	−0.0055 (11)	−0.0038 (11)
C8	0.0403 (14)	0.0266 (12)	0.0352 (13)	−0.0088 (10)	−0.0054 (11)	−0.0026 (10)
C9	0.0393 (14)	0.0340 (13)	0.0384 (14)	−0.0108 (11)	−0.0056 (11)	0.0022 (11)
C10	0.0616 (18)	0.0466 (16)	0.0452 (16)	−0.0243 (14)	0.0038 (13)	−0.0021 (12)
C11	0.073 (2)	0.0474 (16)	0.0530 (17)	−0.0343 (15)	−0.0034 (15)	−0.0079 (13)
C12	0.0406 (14)	0.0370 (13)	0.0342 (13)	−0.0162 (11)	−0.0066 (11)	−0.0048 (10)
C13	0.0510 (17)	0.0476 (16)	0.0471 (16)	−0.0056 (13)	−0.0098 (13)	−0.0090 (13)
C14	0.058 (2)	0.075 (2)	0.060 (2)	−0.0089 (17)	−0.0010 (16)	−0.0314 (18)
C15	0.085 (3)	0.119 (3)	0.0406 (19)	−0.058 (3)	−0.0033 (18)	−0.015 (2)
C16	0.100 (3)	0.090 (3)	0.051 (2)	−0.060 (2)	−0.0364 (19)	0.0222 (18)
C17	0.0598 (18)	0.0434 (16)	0.0560 (18)	−0.0213 (14)	−0.0231 (15)	0.0053 (13)
C18	0.0382 (15)	0.0430 (15)	0.0606 (18)	−0.0032 (12)	−0.0190 (13)	−0.0143 (13)
C19	0.0502 (16)	0.0426 (15)	0.0574 (17)	−0.0055 (13)	−0.0212 (14)	−0.0169 (13)
C20	0.0395 (14)	0.0312 (13)	0.0373 (14)	−0.0073 (11)	−0.0050 (11)	−0.0007 (10)
C21	0.0378 (14)	0.0419 (15)	0.0649 (19)	−0.0023 (12)	−0.0174 (13)	−0.0125 (13)
C22	0.0394 (15)	0.0435 (15)	0.0583 (18)	−0.0051 (12)	−0.0172 (13)	−0.0162 (13)
C23	0.0444 (15)	0.0336 (13)	0.0377 (14)	−0.0074 (12)	−0.0033 (12)	−0.0041 (11)
C24	0.0399 (14)	0.0338 (13)	0.0422 (15)	−0.0002 (11)	−0.0099 (12)	−0.0005 (11)
C25	0.0368 (13)	0.0295 (12)	0.0388 (14)	−0.0076 (11)	−0.0055 (11)	−0.0001 (10)
C26	0.0418 (14)	0.0391 (14)	0.0387 (14)	−0.0109 (12)	−0.0087 (12)	0.0033 (11)
C27	0.0538 (18)	0.0651 (19)	0.0487 (17)	−0.0134 (15)	−0.0184 (14)	0.0038 (14)
C28	0.0449 (16)	0.0506 (17)	0.066 (2)	0.0073 (13)	−0.0163 (14)	−0.0030 (14)
C29	0.0369 (14)	0.0389 (14)	0.0417 (15)	−0.0020 (11)	−0.0032 (11)	−0.0002 (11)
C30	0.0590 (19)	0.0453 (17)	0.0597 (19)	−0.0100 (14)	−0.0047 (15)	0.0068 (14)
C31	0.071 (2)	0.086 (3)	0.053 (2)	−0.015 (2)	0.0053 (17)	0.0190 (19)
C32	0.073 (2)	0.104 (3)	0.0430 (19)	−0.012 (2)	0.0016 (17)	−0.010 (2)
C33	0.092 (3)	0.068 (2)	0.064 (2)	−0.022 (2)	0.0077 (19)	−0.0271 (18)
C34	0.078 (2)	0.0448 (17)	0.0531 (18)	−0.0168 (16)	0.0050 (16)	−0.0058 (14)

Geometric parameters (Å, º)

Ni—O9	2.0104 (18)	C10—H10A	0.9600
Ni—O6	2.0506 (18)	C10—H10B	0.9600
Ni—N5	2.0892 (19)	C10—H10C	0.9600
Ni—N1	2.0892 (19)	C11—H11A	0.9600
Ni—O3	2.0920 (19)	C11—H11B	0.9600
Ni—O4	2.287 (2)	C11—H11C	0.9600
O1—C7	1.240 (3)	C12—C17	1.371 (3)
O2—C24	1.247 (3)	C12—C13	1.380 (3)
O3—N9	1.258 (3)	C13—C14	1.383 (4)
O4—N9	1.263 (3)	C13—H13	0.9300
O5—N9	1.197 (3)	C14—C15	1.364 (5)
O6—N10	1.272 (3)	C14—H14	0.9300
O7—N10	1.227 (3)	C15—C16	1.381 (5)
O8—N10	1.212 (3)	C15—H15	0.9300
O9—H9A	0.811 (10)	C16—C17	1.379 (4)
O9—H9B	0.817 (10)	C16—H16	0.9300
N1—C5	1.338 (3)	C17—H17	0.9300
N1—C1	1.339 (3)	C18—C19	1.379 (3)
N2—C6	1.272 (3)	C18—H18	0.9300
N2—C8	1.389 (3)	C19—C20	1.382 (4)
N3—C9	1.344 (3)	C19—H19	0.9300
N3—N4	1.392 (3)	C20—C21	1.380 (3)
N3—C11	1.441 (3)	C20—C23	1.469 (3)
N4—C7	1.391 (3)	C21—C22	1.377 (3)
N4—C12	1.436 (3)	C21—H21	0.9300
N5—C18	1.329 (3)	C22—H22	0.9300
N5—C22	1.338 (3)	C23—H23	0.9300
N6—C23	1.273 (3)	C24—C25	1.426 (3)
N6—C25	1.392 (3)	C25—C26	1.381 (3)
N7—C26	1.335 (3)	C26—C27	1.489 (4)
N7—N8	1.390 (3)	C27—H27A	0.9600
N7—C28	1.439 (3)	C27—H27B	0.9600
N8—C24	1.380 (3)	C27—H27C	0.9600
N8—C29	1.430 (3)	C28—H28A	0.9600
C1—C2	1.375 (3)	C28—H28B	0.9600
C1—H1	0.9300	C28—H28C	0.9600
C2—C3	1.392 (3)	C29—C34	1.369 (4)
C2—H2	0.9300	C29—C30	1.379 (4)
C3—C4	1.380 (3)	C30—C31	1.376 (4)
C3—C6	1.468 (3)	C30—H30	0.9300
C4—C5	1.376 (3)	C31—C32	1.363 (5)
C4—H4	0.9300	C31—H31	0.9300
C5—H5	0.9300	C32—C33	1.362 (5)
C6—H6	0.9300	C32—H32	0.9300
C7—C8	1.422 (3)	C33—C34	1.384 (4)
C8—C9	1.382 (3)	C33—H33	0.9300
C9—C10	1.485 (3)	C34—H34	0.9300
O9—Ni—O6	89.89 (8)	N3—C11—H11B	109.5
O9—Ni—N5	90.30 (7)	H11A—C11—H11B	109.5
O6—Ni—N5	88.87 (8)	N3—C11—H11C	109.5
O9—Ni—N1	94.27 (7)	H11A—C11—H11C	109.5
O6—Ni—N1	90.90 (8)	H11B—C11—H11C	109.5
N5—Ni—N1	175.42 (8)	C17—C12—C13	121.2 (2)
O9—Ni—O3	96.10 (8)	C17—C12—N4	119.4 (2)
O6—Ni—O3	173.65 (8)	C13—C12—N4	119.3 (2)
N5—Ni—O3	93.17 (8)	C12—C13—C14	118.7 (3)
N1—Ni—O3	86.59 (8)	C12—C13—H13	120.7
O9—Ni—O4	153.77 (8)	C14—C13—H13	120.7
O6—Ni—O4	116.31 (8)	C15—C14—C13	120.6 (3)
N5—Ni—O4	91.39 (7)	C15—C14—H14	119.7
N1—Ni—O4	84.61 (8)	C13—C14—H14	119.7
O3—Ni—O4	57.67 (8)	C14—C15—C16	120.3 (3)
N9—O3—Ni	98.59 (16)	C14—C15—H15	119.9
N9—O4—Ni	89.21 (16)	C16—C15—H15	119.9
N10—O6—Ni	114.13 (16)	C17—C16—C15	119.8 (3)
Ni—O9—H9A	116 (2)	C17—C16—H16	120.1
Ni—O9—H9B	118 (2)	C15—C16—H16	120.1
H9A—O9—H9B	107 (3)	C12—C17—C16	119.5 (3)
C5—N1—C1	117.2 (2)	C12—C17—H17	120.2
C5—N1—Ni	119.57 (16)	C16—C17—H17	120.2
C1—N1—Ni	122.46 (16)	N5—C18—C19	123.8 (2)
C6—N2—C8	120.7 (2)	N5—C18—H18	118.1
C9—N3—N4	108.51 (18)	C19—C18—H18	118.1
C9—N3—C11	128.7 (2)	C18—C19—C20	119.8 (2)
N4—N3—C11	121.9 (2)	C18—C19—H19	120.1
C7—N4—N3	108.75 (18)	C20—C19—H19	120.1
C7—N4—C12	123.34 (19)	C21—C20—C19	116.9 (2)
N3—N4—C12	123.45 (19)	C21—C20—C23	122.0 (2)
C18—N5—C22	116.0 (2)	C19—C20—C23	121.0 (2)
C18—N5—Ni	121.16 (17)	C22—C21—C20	119.3 (2)
C22—N5—Ni	121.83 (16)	C22—C21—H21	120.3
C23—N6—C25	120.8 (2)	C20—C21—H21	120.3
C26—N7—N8	108.23 (19)	N5—C22—C21	124.1 (2)
C26—N7—C28	128.6 (2)	N5—C22—H22	117.9
N8—N7—C28	122.9 (2)	C21—C22—H22	117.9
C24—N8—N7	109.4 (2)	N6—C23—C20	120.4 (2)
C24—N8—C29	125.2 (2)	N6—C23—H23	119.8
N7—N8—C29	123.9 (2)	C20—C23—H23	119.8
O5—N9—O3	121.0 (3)	O2—C24—N8	122.2 (2)
O5—N9—O4	124.6 (3)	O2—C24—C25	132.5 (2)
O3—N9—O4	114.4 (2)	N8—C24—C25	105.2 (2)
O8—N10—O7	123.6 (3)	C26—C25—N6	123.2 (2)
O8—N10—O6	119.3 (2)	C26—C25—C24	107.7 (2)
O7—N10—O6	117.1 (3)	N6—C25—C24	128.8 (2)
N1—C1—C2	122.6 (2)	N7—C26—C25	109.4 (2)
N1—C1—H1	118.7	N7—C26—C27	122.4 (2)
C2—C1—H1	118.7	C25—C26—C27	128.1 (2)
C1—C2—C3	120.2 (2)	C26—C27—H27A	109.5
C1—C2—H2	119.9	C26—C27—H27B	109.5
C3—C2—H2	119.9	H27A—C27—H27B	109.5
C4—C3—C2	116.7 (2)	C26—C27—H27C	109.5
C4—C3—C6	122.6 (2)	H27A—C27—H27C	109.5
C2—C3—C6	120.5 (2)	H27B—C27—H27C	109.5
C5—C4—C3	119.9 (2)	N7—C28—H28A	109.5
C5—C4—H4	120.1	N7—C28—H28B	109.5
C3—C4—H4	120.1	H28A—C28—H28B	109.5
N1—C5—C4	123.2 (2)	N7—C28—H28C	109.5
N1—C5—H5	118.4	H28A—C28—H28C	109.5
C4—C5—H5	118.4	H28B—C28—H28C	109.5
N2—C6—C3	120.4 (2)	C34—C29—C30	120.1 (3)
N2—C6—H6	119.8	C34—C29—N8	121.0 (2)
C3—C6—H6	119.8	C30—C29—N8	118.8 (2)
O1—C7—N4	123.2 (2)	C31—C30—C29	119.7 (3)
O1—C7—C8	131.3 (2)	C31—C30—H30	120.2
N4—C7—C8	105.54 (19)	C29—C30—H30	120.2
C9—C8—N2	123.0 (2)	C32—C31—C30	120.4 (3)
C9—C8—C7	107.9 (2)	C32—C31—H31	119.8
N2—C8—C7	128.6 (2)	C30—C31—H31	119.8
N3—C9—C8	109.2 (2)	C33—C32—C31	119.9 (3)
N3—C9—C10	122.8 (2)	C33—C32—H32	120.1
C8—C9—C10	128.0 (2)	C31—C32—H32	120.1
C9—C10—H10A	109.5	C32—C33—C34	120.7 (3)
C9—C10—H10B	109.5	C32—C33—H33	119.7
H10A—C10—H10B	109.5	C34—C33—H33	119.7
C9—C10—H10C	109.5	C29—C34—C33	119.3 (3)
H10A—C10—H10C	109.5	C29—C34—H34	120.3
H10B—C10—H10C	109.5	C33—C34—H34	120.3
N3—C11—H11A	109.5
O9—Ni—O3—N9	−177.49 (15)	N4—C7—C8—N2	173.3 (2)
N5—Ni—O3—N9	91.87 (15)	N4—N3—C9—C8	−2.9 (3)
N1—Ni—O3—N9	−83.55 (15)	C11—N3—C9—C8	−172.0 (3)
O4—Ni—O3—N9	2.22 (13)	N4—N3—C9—C10	174.7 (2)
O9—Ni—O4—N9	−1.5 (2)	C11—N3—C9—C10	5.6 (4)
O6—Ni—O4—N9	175.51 (13)	N2—C8—C9—N3	−171.6 (2)
N5—Ni—O4—N9	−95.06 (15)	C7—C8—C9—N3	1.1 (3)
N1—Ni—O4—N9	87.18 (15)	N2—C8—C9—C10	11.0 (4)
O3—Ni—O4—N9	−2.19 (13)	C7—C8—C9—C10	−176.3 (3)
O9—Ni—O6—N10	−167.43 (16)	C7—N4—C12—C17	54.0 (3)
N5—Ni—O6—N10	−77.13 (17)	N3—N4—C12—C17	−99.6 (3)
N1—Ni—O6—N10	98.30 (17)	C7—N4—C12—C13	−121.9 (3)
O4—Ni—O6—N10	13.87 (19)	N3—N4—C12—C13	84.5 (3)
O9—Ni—N1—C5	−159.00 (19)	C17—C12—C13—C14	0.1 (4)
O6—Ni—N1—C5	−69.05 (19)	N4—C12—C13—C14	176.0 (2)
O3—Ni—N1—C5	105.12 (19)	C12—C13—C14—C15	−1.0 (5)
O4—Ni—N1—C5	47.30 (19)	C13—C14—C15—C16	1.1 (5)
O9—Ni—N1—C1	31.1 (2)	C14—C15—C16—C17	−0.2 (5)
O6—Ni—N1—C1	121.0 (2)	C13—C12—C17—C16	0.8 (4)
O3—Ni—N1—C1	−64.8 (2)	N4—C12—C17—C16	−175.1 (2)
O4—Ni—N1—C1	−122.6 (2)	C15—C16—C17—C12	−0.7 (4)
C9—N3—N4—C7	3.6 (3)	C22—N5—C18—C19	−3.1 (4)
C11—N3—N4—C7	173.6 (2)	Ni—N5—C18—C19	165.3 (2)
C9—N3—N4—C12	160.5 (2)	N5—C18—C19—C20	0.1 (4)
C11—N3—N4—C12	−29.5 (4)	C18—C19—C20—C21	3.6 (4)
O9—Ni—N5—C18	25.5 (2)	C18—C19—C20—C23	−172.8 (2)
O6—Ni—N5—C18	−64.4 (2)	C19—C20—C21—C22	−4.2 (4)
O3—Ni—N5—C18	121.6 (2)	C23—C20—C21—C22	172.2 (2)
O4—Ni—N5—C18	179.3 (2)	C18—N5—C22—C21	2.5 (4)
O9—Ni—N5—C22	−166.8 (2)	Ni—N5—C22—C21	−165.9 (2)
O6—Ni—N5—C22	103.4 (2)	C20—C21—C22—N5	1.2 (4)
O3—Ni—N5—C22	−70.6 (2)	C25—N6—C23—C20	−172.3 (2)
O4—Ni—N5—C22	−12.9 (2)	C21—C20—C23—N6	15.8 (4)
C26—N7—N8—C24	0.7 (3)	C19—C20—C23—N6	−168.0 (2)
C28—N7—N8—C24	−173.9 (2)	N7—N8—C24—O2	−179.4 (2)
C26—N7—N8—C29	167.2 (2)	C29—N8—C24—O2	14.3 (4)
C28—N7—N8—C29	−7.3 (4)	N7—N8—C24—C25	−0.7 (3)
Ni—O3—N9—O5	176.1 (2)	C29—N8—C24—C25	−167.1 (2)
Ni—O3—N9—O4	−3.7 (2)	C23—N6—C25—C26	−173.7 (2)
Ni—O4—N9—O5	−176.5 (3)	C23—N6—C25—C24	13.5 (4)
Ni—O4—N9—O3	3.4 (2)	O2—C24—C25—C26	179.0 (3)
Ni—O6—N10—O8	−8.0 (3)	N8—C24—C25—C26	0.5 (3)
Ni—O6—N10—O7	172.83 (18)	O2—C24—C25—N6	−7.3 (5)
C5—N1—C1—C2	−2.3 (4)	N8—C24—C25—N6	174.3 (2)
Ni—N1—C1—C2	167.9 (2)	N8—N7—C26—C25	−0.3 (3)
N1—C1—C2—C3	−0.9 (4)	C28—N7—C26—C25	173.8 (3)
C1—C2—C3—C4	3.9 (4)	N8—N7—C26—C27	178.0 (2)
C1—C2—C3—C6	−171.5 (2)	C28—N7—C26—C27	−7.8 (4)
C2—C3—C4—C5	−3.9 (4)	N6—C25—C26—N7	−174.3 (2)
C6—C3—C4—C5	171.5 (2)	C24—C25—C26—N7	−0.1 (3)
C1—N1—C5—C4	2.3 (4)	N6—C25—C26—C27	7.5 (4)
Ni—N1—C5—C4	−168.1 (2)	C24—C25—C26—C27	−178.4 (3)
C3—C4—C5—N1	0.8 (4)	C24—N8—C29—C34	−116.4 (3)
C8—N2—C6—C3	−171.2 (2)	N7—N8—C29—C34	79.2 (4)
C4—C3—C6—N2	12.3 (4)	C24—N8—C29—C30	60.7 (4)
C2—C3—C6—N2	−172.5 (2)	N7—N8—C29—C30	−103.8 (3)
N3—N4—C7—O1	177.7 (2)	C34—C29—C30—C31	0.1 (5)
C12—N4—C7—O1	20.8 (4)	N8—C29—C30—C31	−177.0 (3)
N3—N4—C7—C8	−2.8 (3)	C29—C30—C31—C32	−0.3 (5)
C12—N4—C7—C8	−159.8 (2)	C30—C31—C32—C33	−0.5 (6)
C6—N2—C8—C9	−177.2 (2)	C31—C32—C33—C34	1.5 (6)
C6—N2—C8—C7	11.7 (4)	C30—C29—C34—C33	0.9 (5)
O1—C7—C8—C9	−179.5 (3)	N8—C29—C34—C33	177.9 (3)
N4—C7—C8—C9	1.1 (3)	C32—C33—C34—C29	−1.7 (6)
O1—C7—C8—N2	−7.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9A···O2^i	0.81	1.84	2.632 (3)	168
O9—H9B···O1^ii	0.82	1.87	2.659 (3)	162
C10—H10C···O5^iii	0.94	2.57	3.053 (4)	111
C11—H11A···O3^iv	0.96	2.51	3.407 (4)	155
C14—H14···O7^v	0.93	2.46	3.300 (4)	149
C27—H27C···O7^vi	0.96	2.50	3.245 (4)	134
C28—H28C···O7^vii	0.96	2.60	3.179 (4)	119

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