trans-Di­aqua­bis­{2-[3-(di­methyl­amino)­prop-2-enoyl]­pyridine}­nickel(II) bis­(tetra­fluoro­borate) di­methyl­form­amide tetrasolvate

The title compound, [Ni(C₁₀H₁₂N₂O)₂(H₂O)₂](BF₄)₂·4C₃H₇NO, was synthesized by the reaction of 2-[3-(di­methyl­amino)­prop-2-enoyl]­pyridine and Ni(BF₄)₂ in di­methyl­form­amide. It has been characterized by elemental analysis and X-ray diffraction techniques. The crystal structure reveals that the Ni^II atom, on an inversion center, has an NiN₂O₄ octahedral coordination environment with two carbonyl O atoms and two pyridyl N atoms in the equatorial plane and two water mol­ecules in the axial positions. 2-[3-(Di­methyl­amino)­prop-2-enoyl]­pyridine chelates to the Ni atom through the O and pyridine N atoms. Tetra­fluoro­borate counter-anions and di­methyl­form­amide solvent mol­ecules are not coordinated to the central metal ion.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in solvent or counterion
• R factor = 0.074
• wR factor = 0.200
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.743     0.902
            Tmin' and Tmax expected:      0.876     0.902
            RR' =      0.848
            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 .............       0.85
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT214_ALERT_2_C Atom C14     (Anion/Solvent) ADP max/min Ratio         4.80 prolat
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N2
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors  for       C11'
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for         N3
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for         N4
PLAT244_ALERT_4_C Low  Solvent U(eq) as Compared to Neighbors  for         B1
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      29.00 Perc.
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O3
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........        O3'
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C10
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            O1  -NI1 -O1  -C6    109.00100.00   2.577   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          8
            N1  -NI1 -N1  -C1   -152.00100.00   2.577   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N1  -NI1 -N1  -C5     30.00100.00   2.577   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         39
            O3  -C11 -N3  -C12' -125.00  8.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         45
            O3' -C11'-N3  -C13   163.00 21.00   1.555   1.555   1.555   1.555
PLAT731_ALERT_1_C Bond    Calc   1.433(18), Rep    1.432(8) ......       2.25 su-Rat
              C16  -N4      1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      40.70 Deg.
              F4'  -B1   -F3      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      31.60 Deg.
              F3'  -B1   -F4      1.555   1.555   1.555

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

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

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

trans-Diaquabis[2-[3-(dimethylamino)prop-2-enoyl]pyridine]nickel(II) bis(tetrafluoroborate) dimethylformamide tetrasolvate

Crystal data

[Ni(C10H12N2O)2(H2O)2](BF4)2·4C3H7NO	Z = 1
Mr = 913.18	F(000) = 478
Triclinic, P1	Dx = 1.343 Mg m^−3
a = 10.036 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.384 (3) Å	Cell parameters from 652 reflections
c = 13.384 (3) Å	θ = 3.2–23.0°
α = 107.744 (5)°	µ = 0.52 mm^−1
β = 93.331 (5)°	T = 293 K
γ = 118.732 (5)°	Block, green
V = 1129.4 (5) Å^3	0.25 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3835 independent reflections
Radiation source: fine-focus sealed tube	2265 reflections with I > 2s/(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.743, Tmax = 0.902	k = −12→12
5657 measured reflections	l = −14→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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.201	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ^2(Fo^2) + (0.1115P)^2] where P = (Fo^2 + 2Fc^2)/3
3835 reflections	(Δ/σ)max < 0.001
324 parameters	Δρmax = 0.84 e Å^−3
37 restraints	Δρmin = −0.54 e Å^−3

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	Occ. (<1)
Ni1	0.0000	1.0000	1.0000	0.0422 (4)
O1	0.0636 (5)	0.8447 (4)	1.0085 (3)	0.0470 (10)
N1	0.0135 (5)	0.9157 (5)	0.8445 (3)	0.0418 (11)
N2	0.2342 (6)	0.5608 (5)	1.0142 (4)	0.0536 (13)
C1	−0.0127 (7)	0.9592 (7)	0.7651 (5)	0.0509 (15)
H1A	−0.0359	1.0387	0.7803	0.061*
C2	−0.0064 (8)	0.8910 (8)	0.6625 (5)	0.0597 (17)
H2A	−0.0225	0.9257	0.6091	0.072*
C3	0.0239 (8)	0.7699 (8)	0.6381 (5)	0.0635 (18)
H3A	0.0255	0.7195	0.5681	0.076*
C4	0.0516 (7)	0.7259 (7)	0.7208 (5)	0.0540 (16)
H4A	0.0724	0.6448	0.7068	0.065*
C5	0.0486 (6)	0.8020 (6)	0.8239 (4)	0.0409 (13)
C6	0.0846 (6)	0.7735 (6)	0.9222 (4)	0.0398 (13)
C7	0.1389 (7)	0.6697 (7)	0.9149 (5)	0.0478 (14)
H7A	0.1487	0.6161	0.8488	0.057*
C8	0.1774 (7)	0.6481 (7)	1.0060 (5)	0.0491 (15)
H8A	0.1613	0.7016	1.0691	0.059*
C9	0.2788 (8)	0.5558 (8)	1.1166 (6)	0.069 (2)
H9A	0.2542	0.6191	1.1720	0.104*
H9B	0.3894	0.5970	1.1341	0.104*
H9C	0.2225	0.4481	1.1121	0.104*
C10	0.2652 (11)	0.4710 (10)	0.9198 (6)	0.092 (3)
H10A	0.2308	0.4827	0.8565	0.138*
H10B	0.2095	0.3607	0.9095	0.138*
H10C	0.3756	0.5109	0.9320	0.138*
C11	0.6093 (13)	0.5298 (16)	0.6777 (10)	0.106 (7)	0.64 (2)
H11A	0.7102	0.5617	0.6688	0.127*	0.64 (2)
C12	0.3201 (13)	0.359 (2)	0.6150 (14)	0.165 (11)	0.64 (2)
H12A	0.2616	0.2608	0.6251	0.247*	0.64 (2)
H12B	0.2661	0.3526	0.5504	0.247*	0.64 (2)
H12C	0.3304	0.4442	0.6760	0.247*	0.64 (2)
C13	0.487 (3)	0.285 (2)	0.5112 (11)	0.141 (10)	0.64 (2)
H13A	0.3840	0.1958	0.4710	0.211*	0.64 (2)
H13B	0.5493	0.2471	0.5338	0.211*	0.64 (2)
H13C	0.5352	0.3416	0.4663	0.211*	0.64 (2)
O3	0.5784 (15)	0.6128 (15)	0.7602 (10)	0.108 (6)	0.64 (2)
O3'	0.600 (4)	0.598 (5)	0.736 (3)	0.18 (2)	0.36 (2)
C11'	0.449 (4)	0.481 (4)	0.698 (2)	0.18 (3)	0.36 (2)
H11B	0.3600	0.4650	0.7224	0.219*	0.36 (2)
C12'	0.350 (3)	0.232 (2)	0.5342 (19)	0.16 (2)	0.36 (2)
H12D	0.2517	0.2143	0.5503	0.242*	0.36 (2)
H12E	0.3687	0.1542	0.5445	0.242*	0.36 (2)
H12F	0.3454	0.2231	0.4604	0.242*	0.36 (2)
C13'	0.633 (2)	0.435 (4)	0.594 (4)	0.19 (2)	0.36 (2)
H13D	0.6541	0.3560	0.5993	0.286*	0.36 (2)
H13E	0.7060	0.5353	0.6512	0.286*	0.36 (2)
H13F	0.6425	0.4438	0.5255	0.286*	0.36 (2)
C14	0.4328 (11)	1.0661 (11)	0.8836 (9)	0.159 (7)
H14A	0.4441	1.0345	0.9424	0.191*
C15	0.4395 (12)	1.0159 (14)	0.6821 (7)	0.126 (4)
H15A	0.4785	0.9658	0.6296	0.190*
H15B	0.3284	0.9658	0.6562	0.190*
H15C	0.4900	1.1264	0.6934	0.190*
C16	0.5486 (15)	0.9215 (14)	0.7940 (9)	0.147 (4)
H16A	0.5726	0.8845	0.7266	0.220*
H16B	0.6437	0.9907	0.8503	0.220*
H16C	0.4797	0.8324	0.8113	0.220*
B1	0.1042 (10)	0.7621 (10)	0.3590 (6)	0.075 (2)
F1	0.1212 (8)	0.7738 (8)	0.2633 (4)	0.145 (2)
F2	−0.0272 (10)	0.6284 (8)	0.3498 (6)	0.171 (3)
F3	0.2379 (17)	0.805 (4)	0.4221 (16)	0.168 (12)	0.52 (4)
F4	0.049 (4)	0.855 (4)	0.406 (2)	0.200 (13)	0.52 (4)
F3'	0.131 (3)	0.8928 (15)	0.4327 (12)	0.158 (11)	0.48 (4)
F4'	0.179 (3)	0.696 (3)	0.3867 (18)	0.176 (10)	0.48 (4)
N3	0.4744 (8)	0.3885 (8)	0.6050 (5)	0.0828 (19)
N4	0.4718 (8)	1.0044 (8)	0.7837 (5)	0.0818 (19)
O2	0.2371 (5)	1.1800 (5)	1.0426 (3)	0.0574 (11)
H2B	0.2900	1.1860	0.9950	0.069*
H2C	0.2803	1.2471	1.1073	0.069*
O4	0.3877 (12)	1.1488 (12)	0.8901 (9)	0.229 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0527 (8)	0.0454 (7)	0.0353 (6)	0.0324 (6)	0.0096 (5)	0.0126 (5)
O1	0.068 (3)	0.053 (2)	0.033 (2)	0.045 (2)	0.0110 (18)	0.0110 (18)
N1	0.047 (3)	0.042 (3)	0.037 (3)	0.026 (2)	0.007 (2)	0.013 (2)
N2	0.057 (3)	0.046 (3)	0.065 (3)	0.033 (3)	0.009 (3)	0.022 (3)
C1	0.058 (4)	0.057 (4)	0.044 (4)	0.033 (3)	0.010 (3)	0.022 (3)
C2	0.074 (5)	0.067 (4)	0.038 (4)	0.037 (4)	0.005 (3)	0.021 (3)
C3	0.071 (5)	0.073 (5)	0.036 (3)	0.034 (4)	0.013 (3)	0.015 (3)
C4	0.061 (4)	0.058 (4)	0.045 (4)	0.036 (3)	0.016 (3)	0.012 (3)
C5	0.040 (3)	0.039 (3)	0.040 (3)	0.022 (3)	0.010 (2)	0.008 (2)
C6	0.037 (3)	0.035 (3)	0.047 (3)	0.018 (3)	0.009 (2)	0.016 (3)
C7	0.051 (4)	0.047 (3)	0.051 (4)	0.032 (3)	0.013 (3)	0.014 (3)
C8	0.048 (4)	0.042 (3)	0.059 (4)	0.028 (3)	0.011 (3)	0.013 (3)
C9	0.062 (5)	0.060 (4)	0.086 (5)	0.031 (4)	0.002 (4)	0.033 (4)
C10	0.119 (7)	0.111 (6)	0.102 (6)	0.100 (6)	0.033 (5)	0.042 (5)
C11	0.108 (14)	0.19 (2)	0.098 (14)	0.116 (16)	0.050 (12)	0.086 (15)
C12	0.058 (11)	0.18 (2)	0.107 (15)	0.016 (11)	−0.009 (9)	−0.034 (13)
C13	0.22 (3)	0.17 (2)	0.075 (11)	0.14 (2)	0.061 (14)	0.025 (12)
O3	0.125 (11)	0.080 (8)	0.056 (7)	0.056 (7)	−0.037 (7)	−0.042 (6)
O3'	0.25 (4)	0.34 (6)	0.19 (4)	0.25 (4)	0.16 (3)	0.20 (4)
C11'	0.26 (7)	0.23 (6)	0.11 (3)	0.17 (6)	0.02 (4)	0.06 (4)
C12'	0.18 (4)	0.14 (3)	0.053 (18)	0.01 (3)	0.01 (2)	0.016 (18)
C13'	0.09 (3)	0.17 (4)	0.27 (6)	0.05 (3)	0.06 (3)	0.06 (4)
C14	0.032 (5)	0.043 (5)	0.32 (2)	−0.012 (4)	0.007 (8)	0.028 (9)
C15	0.112 (8)	0.181 (11)	0.090 (7)	0.072 (8)	0.026 (6)	0.063 (7)
C16	0.168 (12)	0.170 (11)	0.151 (10)	0.132 (11)	0.024 (8)	0.051 (8)
B1	0.086 (7)	0.086 (7)	0.063 (6)	0.047 (6)	0.028 (5)	0.036 (5)
F1	0.211 (7)	0.207 (6)	0.083 (4)	0.139 (6)	0.067 (4)	0.078 (4)
F2	0.203 (8)	0.105 (5)	0.157 (6)	0.054 (5)	0.077 (6)	0.032 (4)
F3	0.131 (13)	0.26 (3)	0.121 (14)	0.101 (17)	0.002 (9)	0.085 (17)
F4	0.33 (3)	0.26 (3)	0.21 (2)	0.24 (3)	0.20 (2)	0.158 (19)
F3'	0.29 (3)	0.035 (7)	0.067 (9)	0.050 (11)	0.011 (13)	−0.010 (6)
F4'	0.19 (2)	0.133 (17)	0.21 (2)	0.109 (17)	−0.019 (15)	0.049 (14)
N3	0.085 (5)	0.088 (5)	0.058 (4)	0.043 (4)	−0.004 (4)	0.013 (4)
N4	0.085 (5)	0.084 (5)	0.071 (4)	0.047 (4)	0.023 (3)	0.017 (4)
O2	0.056 (3)	0.053 (2)	0.048 (2)	0.026 (2)	0.0070 (19)	0.006 (2)
O4	0.132 (9)	0.157 (9)	0.238 (12)	0.006 (7)	0.099 (8)	−0.013 (8)

Geometric parameters (Å, º)

Ni1—O1	2.028 (3)	C12—H12B	0.9600
Ni1—O1^i	2.028 (3)	C12—H12C	0.9600
Ni1—N1	2.038 (4)	C13—N3	1.441 (9)
Ni1—N1^i	2.038 (4)	C13—H13A	0.9600
Ni1—O2^i	2.097 (4)	C13—H13B	0.9600
Ni1—O2	2.097 (4)	C13—H13C	0.9600
O1—C6	1.259 (6)	O3'—C11'	1.339 (9)
N1—C1	1.333 (7)	C11'—N3	1.439 (11)
N1—C5	1.344 (7)	C11'—H11B	0.9300
N2—C8	1.307 (7)	C12'—N3	1.440 (10)
N2—C9	1.441 (8)	C12'—H12D	0.9600
N2—C10	1.472 (8)	C12'—H12E	0.9600
C1—C2	1.360 (8)	C12'—H12F	0.9600
C1—H1A	0.9300	C13'—N3	1.452 (11)
C2—C3	1.382 (9)	C13'—H13D	0.9600
C2—H2A	0.9300	C13'—H13E	0.9600
C3—C4	1.380 (9)	C13'—H13F	0.9600
C3—H3A	0.9300	C14—O4	1.134 (10)
C4—C5	1.376 (7)	C14—N4	1.460 (9)
C4—H4A	0.9300	C14—H14A	0.9599
C5—C6	1.494 (8)	C15—N4	1.433 (7)
C6—C7	1.406 (7)	C15—H15A	0.9600
C7—C8	1.371 (8)	C15—H15B	0.9600
C7—H7A	0.9300	C15—H15C	0.9600
C8—H8A	0.9300	C16—N4	1.432 (8)
C9—H9A	0.9600	C16—H16A	0.9600
C9—H9B	0.9600	C16—H16B	0.9600
C9—H9C	0.9600	C16—H16C	0.9600
C10—H10A	0.9600	B1—F3'	1.300 (9)
C10—H10B	0.9600	B1—F4'	1.335 (10)
C10—H10C	0.9600	B1—F3	1.331 (9)
C11—O3	1.332 (8)	B1—F1	1.336 (7)
C11—N3	1.414 (10)	B1—F4	1.345 (10)
C11—H11A	0.9300	B1—F2	1.342 (8)
C12—N3	1.450 (9)	O2—H2B	0.8501
C12—H12A	0.9600	O2—H2C	0.8500
O1—Ni1—O1^i	180.000 (3)	N3—C13—H13C	109.5
O1—Ni1—N1	80.00 (16)	H13A—C13—H13C	109.5
O1^i—Ni1—N1	100.00 (16)	H13B—C13—H13C	109.5
O1—Ni1—N1^i	100.00 (16)	O3'—C11'—N3	95 (3)
O1^i—Ni1—N1^i	80.00 (16)	O3'—C11'—H11B	132.6
N1—Ni1—N1^i	180.000 (2)	N3—C11'—H11B	132.6
O1—Ni1—O2^i	90.27 (16)	N3—C12'—H12D	109.5
O1^i—Ni1—O2^i	89.73 (16)	N3—C12'—H12E	109.5
N1—Ni1—O2^i	90.02 (17)	H12D—C12'—H12E	109.5
N1^i—Ni1—O2^i	89.98 (17)	N3—C12'—H12F	109.5
O1—Ni1—O2	89.73 (16)	H12D—C12'—H12F	109.5
O1^i—Ni1—O2	90.27 (16)	H12E—C12'—H12F	109.5
N1—Ni1—O2	89.98 (17)	N3—C13'—H13D	109.5
N1^i—Ni1—O2	90.02 (17)	N3—C13'—H13E	109.5
O2^i—Ni1—O2	180.0	H13D—C13'—H13E	109.5
C6—O1—Ni1	115.1 (3)	N3—C13'—H13F	109.5
C1—N1—C5	119.6 (5)	H13D—C13'—H13F	109.5
C1—N1—Ni1	126.6 (4)	H13E—C13'—H13F	109.5
C5—N1—Ni1	113.7 (3)	O4—C14—N4	119.5 (12)
C8—N2—C9	121.8 (5)	O4—C14—H14A	120.9
C8—N2—C10	121.2 (5)	N4—C14—H14A	119.6
C9—N2—C10	116.8 (5)	N4—C15—H15A	110.9
N1—C1—C2	122.0 (6)	N4—C15—H15B	109.3
N1—C1—H1A	119.0	H15A—C15—H15B	109.5
C2—C1—H1A	119.0	N4—C15—H15C	108.2
C1—C2—C3	119.6 (6)	H15A—C15—H15C	109.5
C1—C2—H2A	120.2	H15B—C15—H15C	109.5
C3—C2—H2A	120.2	N4—C16—H16A	109.2
C2—C3—C4	118.1 (6)	N4—C16—H16B	110.2
C2—C3—H3A	120.9	H16A—C16—H16B	109.5
C4—C3—H3A	120.9	N4—C16—H16C	109.0
C5—C4—C3	120.0 (6)	H16A—C16—H16C	109.5
C5—C4—H4A	120.0	H16B—C16—H16C	109.5
C3—C4—H4A	120.0	F3'—B1—F4'	116.0 (12)
N1—C5—C4	120.6 (5)	F3'—B1—F3	80.2 (15)
N1—C5—C6	113.4 (4)	F4'—B1—F3	40.7 (11)
C4—C5—C6	126.0 (5)	F3'—B1—F1	113.0 (10)
O1—C6—C7	123.0 (5)	F4'—B1—F1	111.3 (12)
O1—C6—C5	117.4 (4)	F3—B1—F1	112.4 (9)
C7—C6—C5	119.6 (5)	F3'—B1—F4	31.6 (17)
C8—C7—C6	119.6 (5)	F4'—B1—F4	139.2 (15)
C8—C7—H7A	120.2	F3—B1—F4	110.6 (13)
C6—C7—H7A	120.2	F1—B1—F4	107.0 (10)
N2—C8—C7	127.4 (6)	F3'—B1—F2	116.3 (12)
N2—C8—H8A	116.3	F4'—B1—F2	85.1 (14)
C7—C8—H8A	116.3	F3—B1—F2	119.1 (14)
N2—C9—H9A	109.5	F1—B1—F2	112.3 (7)
N2—C9—H9B	109.5	F4—B1—F2	93.2 (16)
H9A—C9—H9B	109.5	C11—N3—C11'	63.5 (15)
N2—C9—H9C	109.5	C11—N3—C12'	170.7 (17)
H9A—C9—H9C	109.5	C11'—N3—C12'	121.2 (15)
H9B—C9—H9C	109.5	C11—N3—C13	121.0 (11)
N2—C10—H10A	109.5	C11'—N3—C13	175.2 (16)
N2—C10—H10B	109.5	C12'—N3—C13	54.1 (12)
H10A—C10—H10B	109.5	C11—N3—C12	119.7 (8)
N2—C10—H10C	109.5	C11'—N3—C12	57.2 (14)
H10A—C10—H10C	109.5	C12'—N3—C12	67.0 (15)
H10B—C10—H10C	109.5	C13—N3—C12	118.6 (10)
O3—C11—N3	113.7 (10)	C11—N3—C13'	56.7 (14)
O3—C11—H11A	123.1	C11'—N3—C13'	120.1 (15)
N3—C11—H11A	123.1	C12'—N3—C13'	117.3 (14)
N3—C12—H12A	109.5	C13—N3—C13'	64.3 (14)
N3—C12—H12B	109.5	C12—N3—C13'	174 (2)
H12A—C12—H12B	109.5	C16—N4—C15	119.7 (7)
N3—C12—H12C	109.5	C16—N4—C14	112.5 (7)
H12A—C12—H12C	109.5	C15—N4—C14	127.8 (7)
H12B—C12—H12C	109.5	Ni1—O2—H2B	120.0
N3—C13—H13A	109.5	Ni1—O2—H2C	120.0
N3—C13—H13B	109.5	H2B—O2—H2C	120.0
H13A—C13—H13B	109.5
O1^i—Ni1—O1—C6	109 (100)	C3—C4—C5—C6	−176.5 (6)
N1—Ni1—O1—C6	1.3 (4)	Ni1—O1—C6—C7	175.7 (4)
N1^i—Ni1—O1—C6	−178.7 (4)	Ni1—O1—C6—C5	−4.6 (6)
O2^i—Ni1—O1—C6	91.2 (4)	N1—C5—C6—O1	6.8 (7)
O2—Ni1—O1—C6	−88.8 (4)	C4—C5—C6—O1	−174.4 (5)
O1—Ni1—N1—C1	−179.3 (5)	N1—C5—C6—C7	−173.5 (5)
O1^i—Ni1—N1—C1	0.7 (5)	C4—C5—C6—C7	5.4 (9)
N1^i—Ni1—N1—C1	−152 (100)	O1—C6—C7—C8	−2.7 (9)
O2^i—Ni1—N1—C1	90.4 (5)	C5—C6—C7—C8	177.6 (5)
O2—Ni1—N1—C1	−89.6 (5)	C9—N2—C8—C7	176.1 (6)
O1—Ni1—N1—C5	2.6 (4)	C10—N2—C8—C7	0.2 (10)
O1^i—Ni1—N1—C5	−177.4 (4)	C6—C7—C8—N2	−177.6 (6)
N1^i—Ni1—N1—C5	30 (100)	O3—C11—N3—C11'	−2 (2)
O2^i—Ni1—N1—C5	−87.7 (4)	O3—C11—N3—C12'	−125 (8)
O2—Ni1—N1—C5	92.3 (4)	O3—C11—N3—C13	179.9 (15)
C5—N1—C1—C2	0.6 (9)	O3—C11—N3—C12	9 (2)
Ni1—N1—C1—C2	−177.4 (5)	O3—C11—N3—C13'	−177 (3)
N1—C1—C2—C3	1.7 (10)	O3'—C11'—N3—C11	3 (3)
C1—C2—C3—C4	−2.0 (10)	O3'—C11'—N3—C12'	174 (3)
C2—C3—C4—C5	0.0 (10)	O3'—C11'—N3—C13	163 (21)
C1—N1—C5—C4	−2.6 (8)	O3'—C11'—N3—C12	−165 (5)
Ni1—N1—C5—C4	175.7 (4)	O3'—C11'—N3—C13'	8 (5)
C1—N1—C5—C6	176.4 (5)	O4—C14—N4—C16	171.3 (11)
Ni1—N1—C5—C6	−5.4 (6)	O4—C14—N4—C15	−9.9 (16)
C3—C4—C5—N1	2.3 (9)

Symmetry code: (i) −x, −y+2, −z+2.