Electronic structure of the nickel(II) complex of the Schiff base of (S)-N-(2-benzoylphenyl)-1-benzylprolinamide and glycine

Kožíšek, J.; Fronc, M.; Skubák, P.; Popkov, A.; Breza, M.; Fuess, H.; Paulmann, C.

doi:10.1107/S0108767304017131

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Electronic structure of the nickel(II) complex of the Schiff base of (S)-N-(2-benzoylphenyl)-1-benzylprolinamide and glycine

J. Kožíšek, M. Fronc, P. Skubák, A. Popkov, M. Breza, H. Fuess and C. Paulmann

The experimental charge density of the Ni^II complex of the Schiff base of (S)-N-(2-benzoylphenyl)-1-benzylprolinamide and glycine was derived from high-resolution single-crystal X-ray diffraction data (λ = 0.5604 Å) at low temperature (100 K) with synchrotron radiation at the beamline F1 using a CCD area detector. The central Ni atom is pseudo-square-planar coordinated by three N atoms [1.9414 (3), 1.8559 (3) and 1.8533 (3) Å] and by one O atom [1.8620 (4) Å]. The N(1) atom is 0.359 Å above the plane defined by the atoms Ni(1), N(2) and N(3). The d-orbital population analysis reveals an oxidation state for the Ni atom of +2 with the configuration d⁸ and a hole mainly in the d_x²_−y² orbital, located in the plane of the four ligating atoms. The prochiral reaction centre was examined by topological analysis.

Keywords: charge density; nickel; asymmetric synthesis; amino acids; chiral.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108767304017131/xc5005sup1.cif Contains datablock global
	Structure factor file (CIF format) https://doi.org/10.1107/S0108767304017131/xc5005Isup2.hkl Contains datablock I

CCDC reference: 251368

Comment top

The main part of the paper will be sent as WORD·DOC file

Computing details top

Program(s) used to refine structure: Koritsanszky et al., (2003); molecular graphics: Koritsanszky et al., (2003); software used to prepare material for publication: Koritsanszky et al., (2003).

Figures top

(I) top

Crystal data top

C₂₇H₂₅NiN₃O₃	V = 2278.06 Å³
M_r = 498.21	Z = ?
Orthorhombic, P2₁2₁2₁	? radiation, λ = ? Å
a = 8.9817 Å	Block, orange
b = 9.6588 Å	0.44 × 0.11 × 0.09 mm
c = 26.2593 Å

Data collection top

h = ?→?	l = ?→?
k = ?→?

Refinement top

Refinement on F²	26433 reflections
Least-squares matrix: full	905 parameters
R[F² > 2σ(F²)] = 0.015	0 restraints
wR(F²) = 0.032	w2 = q/[s²(F_o²) + (0.00 P)² + 1.00 P + 0.00 + 0.00 sin(th)] where P = (0.3333 F_o² + 0.6667 F_c²) q = 1.0
S = 1.55	(Δ/σ)_max = 0.005

Crystal data top

C₂₇H₂₅NiN₃O₃	c = 26.2593 Å
M_r = 498.21	V = 2278.06 Å³
Orthorhombic, P2₁2₁2₁	Z = ?
a = 8.9817 Å	? radiation, λ = ? Å
b = 9.6588 Å	0.44 × 0.11 × 0.09 mm

Data collection top

Refinement top

R[F² > 2σ(F²)] = 0.015	26433 reflections
wR(F²) = 0.032	905 parameters
S = 1.55	0 restraints

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
NI2+(1)	0.00878 (2)	0.01229 (2)	0.01210 (2)	0.00140 (2)	−0.00066 (2)	−0.00029 (2)
O(1)	0.0166 (1)	0.0212 (1)	0.0178 (1)	0.0086 (1)	0.0028 (1)	0.0027 (1)
O(2)	0.0131 (1)	0.0235 (2)	0.0164 (1)	0.0067 (1)	−0.0008 (1)	0.0011 (1)
O(3)	0.0152 (1)	0.0408 (3)	0.0217 (2)	0.0140 (1)	−0.0029 (1)	−0.0028 (2)
N(1)	0.01095 (8)	0.01387 (10)	0.01320 (8)	0.00038 (7)	−0.00082 (7)	0.00129 (7)
N(2)	0.00922 (8)	0.01529 (10)	0.01239 (9)	0.00184 (7)	0.00018 (7)	0.00103 (7)
N(3)	0.00922 (7)	0.01703 (12)	0.01315 (9)	0.00194 (7)	−0.00013 (7)	−0.00081 (8)
C(1)	0.0147 (1)	0.0179 (1)	0.0203 (1)	0.0009 (1)	−0.0012 (1)	0.0060 (1)
C(2)	0.0161 (1)	0.0142 (1)	0.0264 (2)	−0.0007 (1)	0.0013 (1)	0.0024 (1)
C(3)	0.0124 (1)	0.0167 (1)	0.0222 (1)	−0.0010 (1)	0.0020 (1)	0.0027 (1)
C(4)	0.01172 (8)	0.01395 (10)	0.01307 (9)	0.00090 (8)	0.00112 (7)	0.00073 (8)
C(5)	0.01087 (9)	0.01495 (11)	0.01366 (10)	0.00251 (8)	0.00132 (8)	0.00153 (8)
C(6)	0.00913 (8)	0.01577 (11)	0.01293 (9)	0.00055 (7)	−0.00011 (7)	0.00162 (8)
C(7)	0.00913 (9)	0.02919 (18)	0.01563 (12)	0.0013 (1)	−0.00061 (9)	0.00415 (11)
C(8)	0.0108 (1)	0.0369 (2)	0.0169 (1)	0.0020 (1)	−0.0019 (1)	0.0051 (1)
C(9)	0.0131 (1)	0.0337 (2)	0.0150 (1)	0.0017 (1)	−0.0023 (1)	0.0034 (1)
C(10)	0.0125 (1)	0.0248 (2)	0.0131 (1)	0.0014 (1)	−0.0009 (1)	0.0011 (1)
C(11)	0.00995 (8)	0.01550 (11)	0.01264 (9)	0.00067 (7)	−0.00012 (8)	0.00059 (8)
C(12)	0.00996 (7)	0.01395 (10)	0.01300 (9)	0.00051 (7)	0.00046 (7)	−0.00040 (8)
C(13)	0.01156 (9)	0.01338 (10)	0.01459 (10)	0.00001 (7)	0.00192 (8)	−0.00014 (8)
C(14)	0.0159 (1)	0.0132 (1)	0.0204 (1)	0.0005 (1)	0.0023 (1)	0.0011 (1)
C(15)	0.0174 (1)	0.0174 (1)	0.0223 (2)	−0.0011 (1)	0.0027 (1)	0.0053 (1)
C(16)	0.0158 (1)	0.0232 (2)	0.0170 (1)	−0.0008 (1)	0.0031 (1)	0.0037 (1)
C(17)	0.0207 (1)	0.0206 (1)	0.0170 (1)	−0.0007 (1)	0.0062 (1)	−0.0020 (1)
C(18)	0.0198 (1)	0.0148 (1)	0.0172 (1)	−0.0020 (1)	0.0060 (1)	−0.0022 (1)
C(19)	0.01001 (9)	0.02726 (18)	0.01684 (12)	0.00398 (10)	0.00052 (8)	−0.00069 (11)
C(20)	0.0114 (1)	0.0235 (2)	0.0166 (1)	0.0062 (1)	−0.0020 (1)	−0.0034 (1)
C(21)	0.0146 (1)	0.0193 (1)	0.0142 (1)	−0.0021 (1)	−0.0020 (1)	0.0002 (1)
C(22)	0.0156 (1)	0.0188 (1)	0.0153 (1)	−0.0041 (1)	−0.0005 (1)	−0.0013 (1)
C(23)	0.0190 (1)	0.0289 (2)	0.0188 (1)	−0.0081 (1)	0.0036 (1)	−0.0051 (1)
C(24)	0.0310 (2)	0.0434 (3)	0.0194 (2)	−0.0184 (2)	0.0043 (2)	0.0004 (2)
C(25)	0.0428 (3)	0.0397 (3)	0.0239 (2)	−0.0203 (3)	−0.0072 (2)	0.0126 (2)
C(26)	0.0344 (3)	0.0250 (2)	0.0320 (2)	−0.0087 (2)	−0.0122 (2)	0.0098 (2)
C(27)	0.0205 (1)	0.0195 (1)	0.0248 (2)	−0.0032 (1)	−0.0045 (1)	0.0020 (1)

Geometric parameters (Å, º) top

NI2+(1)—O(2)	1.8620 (4)	C(12)—C(13)	1.4965 (4)
NI2+(1)—N(1)	1.9413 (3)	C(13)—C(14)	1.3987 (5)
NI2+(1)—N(2)	1.8559 (3)	C(13)—C(18)	1.3962 (5)
NI2+(1)—N(3)	1.8533 (3)	C(14)—C(15)	1.3950 (6)
O(1)—C(5)	1.2288 (5)	C(14)—H(14A)	1.0829 (1)
O(2)—C(20)	1.2933 (6)	C(15)—C(16)	1.3942 (7)
O(3)—C(20)	1.2249 (5)	C(15)—H(15A)	1.0839 (1)
N(1)—C(1)	1.4927 (5)	C(16)—C(17)	1.3939 (7)
N(1)—C(4)	1.4936 (4)	C(16)—H(16A)	1.0837 (1)
N(1)—C(21)	1.5000 (5)	C(17)—C(18)	1.3952 (5)
N(2)—C(5)	1.3750 (4)	C(17)—H(17A)	1.0824 (1)
N(2)—C(6)	1.3897 (4)	C(18)—H(18A)	1.0831 (1)
N(3)—C(12)	1.2982 (4)	C(19)—C(20)	1.5205 (6)
N(3)—C(19)	1.4691 (4)	C(19)—H(19B)	1.0926 (1)
C(1)—C(2)	1.5123 (6)	C(19)—H(19A)	1.0918 (1)
C(1)—H(1B)	1.0921 (1)	C(21)—C(22)	1.5067 (6)
C(1)—H(1A)	1.0903 (1)	C(21)—H(21B)	1.0916 (1)
C(2)—C(3)	1.5324 (6)	C(21)—H(21A)	1.0918 (1)
C(2)—H(2B)	1.0932 (1)	C(22)—C(23)	1.4006 (6)
C(2)—H(2A)	1.0897 (1)	C(22)—C(27)	1.3979 (7)
C(3)—C(4)	1.5555 (5)	C(23)—C(24)	1.3931 (9)
C(3)—H(3B)	1.0929 (1)	C(23)—H(23A)	1.0841 (1)
C(3)—H(3A)	1.0921 (1)	C(24)—C(25)	1.4024 (15)
C(4)—C(5)	1.5090 (5)	C(24)—H(24A)	1.0811 (1)
C(4)—H(4A)	1.0986 (1)	C(25)—C(26)	1.3953 (13)
C(6)—C(7)	1.4155 (4)	C(25)—H(25A)	1.0837 (1)
C(6)—C(11)	1.4213 (4)	C(26)—C(27)	1.3916 (8)
C(7)—C(8)	1.3807 (6)	C(26)—H(26A)	1.0851 (1)
C(7)—H(7A)	1.0832 (1)	C(27)—H(27A)	1.0845 (1)
C(8)—C(9)	1.3968 (6)	H(1B)—H(1A)	1.7791 (1)
C(8)—H(8A)	1.0824 (1)	H(1B)—H(3A)ⁱ	2.0658 (5)
C(9)—C(10)	1.3815 (5)	H(2B)—H(2A)	1.7798 (1)
C(9)—H(9A)	1.0826 (1)	H(3B)—H(3A)	1.7762 (1)
C(10)—C(11)	1.4154 (5)	H(19B)—H(19A)	1.7697 (1)
C(10)—H(10A)	1.0846 (1)	H(21B)—H(21A)	1.7629 (1)
C(11)—C(12)	1.4606 (4)

O(2)—NI2+(1)—N(1)	89.031 (16)	C(11)—C(12)—C(13)	117.86 (3)
O(2)—NI2+(1)—N(2)	175.892 (19)	C(12)—C(13)—C(14)	119.67 (3)
O(2)—NI2+(1)—N(3)	87.348 (16)	C(12)—C(13)—C(18)	120.55 (3)
N(1)—NI2+(1)—N(2)	88.659 (13)	C(14)—C(13)—C(18)	119.77 (3)
N(1)—NI2+(1)—N(3)	168.551 (14)	C(13)—C(14)—C(15)	119.93 (4)
N(2)—NI2+(1)—N(3)	95.556 (14)	C(13)—C(14)—H(14A)	120.04 (2)
NI2+(1)—O(2)—C(20)	115.31 (3)	C(15)—C(14)—H(14A)	120.03 (3)
NI2+(1)—N(1)—C(1)	113.02 (3)	C(14)—C(15)—C(16)	120.13 (4)
NI2+(1)—N(1)—C(4)	107.52 (2)	C(14)—C(15)—H(15A)	119.95 (3)
NI2+(1)—N(1)—C(21)	107.28 (2)	C(16)—C(15)—H(15A)	119.92 (2)
C(1)—N(1)—C(4)	105.17 (3)	C(15)—C(16)—C(17)	120.03 (4)
C(1)—N(1)—C(21)	110.16 (3)	C(15)—C(16)—H(16A)	120.11 (2)
C(4)—N(1)—C(21)	113.79 (3)	C(17)—C(16)—H(16A)	119.86 (2)
NI2+(1)—N(2)—C(5)	114.05 (2)	C(16)—C(17)—C(18)	119.94 (4)
NI2+(1)—N(2)—C(6)	125.16 (2)	C(16)—C(17)—H(17A)	120.16 (2)
C(5)—N(2)—C(6)	120.74 (3)	C(18)—C(17)—H(17A)	119.90 (3)
NI2+(1)—N(3)—C(12)	128.62 (2)	C(13)—C(18)—C(17)	120.18 (4)
NI2+(1)—N(3)—C(19)	110.42 (2)	C(13)—C(18)—H(18A)	119.91 (2)
C(12)—N(3)—C(19)	120.14 (3)	C(17)—C(18)—H(18A)	119.90 (3)
N(1)—C(1)—C(2)	103.08 (3)	N(3)—C(19)—C(20)	109.44 (3)
N(1)—C(1)—H(1B)	111.189 (19)	N(3)—C(19)—H(19B)	109.83 (2)
N(1)—C(1)—H(1A)	111.19 (2)	N(3)—C(19)—H(19A)	109.81 (2)
C(2)—C(1)—H(1B)	111.03 (2)	C(20)—C(19)—H(19B)	109.82 (2)
C(2)—C(1)—H(1A)	111.05 (2)	C(20)—C(19)—H(19A)	109.70 (2)
H(1B)—C(1)—H(1A)	109.2119 (1)	H(19B)—C(19)—H(19A)	108.2273 (1)
C(1)—C(2)—C(3)	102.54 (3)	O(2)—C(20)—O(3)	124.89 (5)
C(1)—C(2)—H(2B)	111.18 (2)	O(2)—C(20)—C(19)	114.52 (3)
C(1)—C(2)—H(2A)	111.30 (2)	O(3)—C(20)—C(19)	120.59 (4)
C(3)—C(2)—H(2B)	111.17 (3)	N(1)—C(21)—C(22)	113.95 (3)
C(3)—C(2)—H(2A)	111.30 (2)	N(1)—C(21)—H(21B)	108.728 (19)
H(2B)—C(2)—H(2A)	109.2410 (1)	N(1)—C(21)—H(21A)	108.81 (2)
C(2)—C(3)—C(4)	104.96 (3)	C(22)—C(21)—H(21B)	108.75 (2)
C(2)—C(3)—H(3B)	110.71 (3)	C(22)—C(21)—H(21A)	108.74 (2)
C(2)—C(3)—H(3A)	110.67 (2)	H(21B)—C(21)—H(21A)	107.6897 (1)
C(4)—C(3)—H(3B)	110.80 (2)	C(21)—C(22)—C(23)	119.80 (4)
C(4)—C(3)—H(3A)	110.91 (2)	C(21)—C(22)—C(27)	121.13 (4)
H(3B)—C(3)—H(3A)	108.7679 (1)	C(23)—C(22)—C(27)	119.05 (5)
N(1)—C(4)—C(3)	105.54 (3)	C(22)—C(23)—C(24)	120.74 (6)
N(1)—C(4)—C(5)	111.16 (3)	C(22)—C(23)—H(23A)	119.80 (3)
N(1)—C(4)—H(4A)	110.168 (18)	C(24)—C(23)—H(23A)	119.46 (4)
C(3)—C(4)—C(5)	109.39 (3)	C(23)—C(24)—C(25)	119.66 (6)
C(3)—C(4)—H(4A)	110.23 (2)	C(23)—C(24)—H(24A)	120.38 (4)
C(5)—C(4)—H(4A)	110.240 (19)	C(25)—C(24)—H(24A)	119.96 (4)
O(1)—C(5)—N(2)	127.80 (4)	C(24)—C(25)—C(26)	119.83 (6)
O(1)—C(5)—C(4)	119.72 (3)	C(24)—C(25)—H(25A)	120.05 (4)
N(2)—C(5)—C(4)	112.38 (3)	C(26)—C(25)—H(25A)	120.11 (5)
N(2)—C(6)—C(7)	120.61 (3)	C(25)—C(26)—C(27)	120.12 (7)
N(2)—C(6)—C(11)	121.79 (3)	C(25)—C(26)—H(26A)	119.87 (5)
C(7)—C(6)—C(11)	117.49 (3)	C(27)—C(26)—H(26A)	120.00 (4)
C(6)—C(7)—C(8)	121.76 (3)	C(22)—C(27)—C(26)	120.58 (6)
C(6)—C(7)—H(7A)	119.10 (2)	C(22)—C(27)—H(27A)	119.62 (3)
C(8)—C(7)—H(7A)	119.14 (2)	C(26)—C(27)—H(27A)	119.80 (4)
C(7)—C(8)—C(9)	120.85 (3)	C(1)—H(1B)—H(1A)	35.3615 (1)
C(7)—C(8)—H(8A)	119.57 (2)	C(1)—H(1B)—H(3A)ⁱ	137.700 (16)
C(9)—C(8)—H(8A)	119.58 (2)	H(1A)—H(1B)—H(3A)ⁱ	112.040 (17)
C(8)—C(9)—C(10)	118.63 (4)	C(1)—H(1A)—H(1B)	35.4267 (1)
C(8)—C(9)—H(9A)	120.69 (2)	C(2)—H(2B)—H(2A)	35.3154 (1)
C(10)—C(9)—H(9A)	120.68 (2)	C(2)—H(2A)—H(2B)	35.4437 (1)
C(9)—C(10)—C(11)	121.95 (3)	C(3)—H(3B)—H(3A)	35.6002 (1)
C(9)—C(10)—H(10A)	119.01 (2)	C(3)—H(3A)—H(1B)ⁱⁱ	112.945 (17)
C(11)—C(10)—H(10A)	119.04 (2)	C(3)—H(3A)—H(3B)	35.6319 (1)
C(6)—C(11)—C(10)	119.26 (3)	H(1B)ⁱⁱ—H(3A)—H(3B)	98.488 (18)
C(6)—C(11)—C(12)	123.65 (3)	C(19)—H(19B)—H(19A)	35.8723 (1)
C(10)—C(11)—C(12)	117.06 (3)	C(19)—H(19A)—H(19B)	35.9004 (1)
N(3)—C(12)—C(11)	122.05 (3)	C(21)—H(21B)—H(21A)	36.1575 (1)
N(3)—C(12)—C(13)	120.08 (3)	C(21)—H(21A)—H(21B)	36.1528 (1)

O(2)—NI2+(1)—N(1)—C(1)	53.0 (1)	H(4A)—C(4)—C(5)—O(1)	32.9 (1)
O(2)—NI2+(1)—N(1)—C(4)	168.6 (1)	H(4A)—C(4)—C(5)—N(2)	−150.5 (1)
N(1)—NI2+(1)—O(2)—C(20)	159.1 (1)	N(2)—C(6)—C(7)—C(8)	178.0 (1)
O(2)—NI2+(1)—N(1)—C(21)	−68.6 (1)	N(2)—C(6)—C(7)—H(7A)	−2.0 (1)
O(2)—NI2+(1)—N(2)—C(5)	−63.6 (3)	N(2)—C(6)—C(11)—C(10)	−179.0 (1)
O(2)—NI2+(1)—N(2)—C(6)	118.8 (3)	N(2)—C(6)—C(11)—C(12)	−1.1 (1)
N(2)—NI2+(1)—O(2)—C(20)	−145.1 (3)	C(11)—C(6)—C(7)—C(8)	1.5 (1)
O(2)—NI2+(1)—N(3)—C(12)	−175.0 (1)	C(7)—C(6)—C(11)—C(10)	−2.6 (1)
O(2)—NI2+(1)—N(3)—C(19)	15.5 (1)	C(7)—C(6)—C(11)—C(12)	175.3 (1)
N(3)—NI2+(1)—O(2)—C(20)	−10.0 (1)	C(11)—C(6)—C(7)—H(7A)	−178.4 (1)
N(2)—NI2+(1)—N(1)—C(1)	−123.6 (1)	C(6)—C(7)—C(8)—C(9)	0.6 (1)
N(2)—NI2+(1)—N(1)—C(4)	−8.0 (1)	C(6)—C(7)—C(8)—H(8A)	−179.4 (1)
N(1)—NI2+(1)—N(2)—C(5)	−7.8 (1)	H(7A)—C(7)—C(8)—C(9)	−179.5 (1)
N(1)—NI2+(1)—N(2)—C(6)	174.6 (1)	H(7A)—C(7)—C(8)—H(8A)	0.6 (1)
N(2)—NI2+(1)—N(1)—C(21)	114.8 (1)	C(7)—C(8)—C(9)—C(10)	−1.6 (1)
N(3)—NI2+(1)—N(1)—C(1)	124.5 (1)	C(7)—C(8)—C(9)—H(9A)	178.3 (1)
N(3)—NI2+(1)—N(1)—C(4)	−119.8 (1)	H(8A)—C(8)—C(9)—C(10)	178.4 (1)
N(1)—NI2+(1)—N(3)—C(12)	113.3 (1)	H(8A)—C(8)—C(9)—H(9A)	−1.8 (1)
N(1)—NI2+(1)—N(3)—C(19)	−56.2 (1)	C(8)—C(9)—C(10)—C(11)	0.5 (1)
N(3)—NI2+(1)—N(1)—C(21)	2.9 (1)	C(8)—C(9)—C(10)—H(10A)	−179.5 (1)
N(3)—NI2+(1)—N(2)—C(5)	161.6 (1)	H(9A)—C(9)—C(10)—C(11)	−179.4 (1)
N(3)—NI2+(1)—N(2)—C(6)	−16.1 (1)	H(9A)—C(9)—C(10)—H(10A)	0.6 (1)
N(2)—NI2+(1)—N(3)—C(12)	2.1 (1)	C(9)—C(10)—C(11)—C(6)	1.7 (1)
N(2)—NI2+(1)—N(3)—C(19)	−167.4 (1)	C(9)—C(10)—C(11)—C(12)	−176.4 (1)
NI2+(1)—O(2)—C(20)—O(3)	−177.4 (1)	H(10A)—C(10)—C(11)—C(6)	−178.3 (1)
NI2+(1)—O(2)—C(20)—C(19)	1.6 (1)	H(10A)—C(10)—C(11)—C(12)	3.6 (1)
NI2+(1)—N(1)—C(1)—C(2)	76.0 (1)	C(6)—C(11)—C(12)—N(3)	−13.6 (1)
NI2+(1)—N(1)—C(1)—H(1B)	−43.0 (1)	C(6)—C(11)—C(12)—C(13)	167.2 (1)
NI2+(1)—N(1)—C(1)—H(1A)	−165.0 (1)	C(10)—C(11)—C(12)—N(3)	164.4 (1)
NI2+(1)—N(1)—C(4)—C(3)	−97.7 (1)	C(10)—C(11)—C(12)—C(13)	−14.9 (1)
NI2+(1)—N(1)—C(4)—C(5)	20.8 (1)	N(3)—C(12)—C(13)—C(14)	103.1 (1)
NI2+(1)—N(1)—C(4)—H(4A)	143.3 (1)	N(3)—C(12)—C(13)—C(18)	−77.8 (1)
NI2+(1)—N(1)—C(21)—C(22)	−39.9 (1)	C(11)—C(12)—C(13)—C(14)	−77.6 (1)
NI2+(1)—N(1)—C(21)—H(21B)	−161.4 (1)	C(11)—C(12)—C(13)—C(18)	101.4 (1)
NI2+(1)—N(1)—C(21)—H(21A)	81.6 (1)	C(12)—C(13)—C(14)—C(15)	−179.9 (1)
C(4)—N(1)—C(1)—C(2)	−41.0 (1)	C(12)—C(13)—C(14)—H(14A)	0.3 (1)
C(1)—N(1)—C(4)—C(3)	23.0 (1)	C(12)—C(13)—C(18)—C(17)	−179.4 (1)
C(1)—N(1)—C(4)—C(5)	141.5 (1)	C(12)—C(13)—C(18)—H(18A)	0.6 (1)
C(4)—N(1)—C(1)—H(1B)	−160.0 (1)	C(18)—C(13)—C(14)—C(15)	1.0 (1)
C(4)—N(1)—C(1)—H(1A)	78.0 (1)	C(14)—C(13)—C(18)—C(17)	−0.3 (1)
C(1)—N(1)—C(4)—H(4A)	−96.0 (1)	C(18)—C(13)—C(14)—H(14A)	−178.8 (1)
C(21)—N(1)—C(1)—C(2)	−164.0 (1)	C(14)—C(13)—C(18)—H(18A)	179.7 (1)
C(1)—N(1)—C(21)—C(22)	−163.3 (1)	C(13)—C(14)—C(15)—C(16)	−0.9 (1)
C(21)—N(1)—C(1)—H(1B)	77.0 (1)	C(13)—C(14)—C(15)—H(15A)	179.0 (1)
C(21)—N(1)—C(1)—H(1A)	−45.0 (1)	H(14A)—C(14)—C(15)—C(16)	179.0 (1)
C(1)—N(1)—C(21)—H(21B)	75.3 (1)	H(14A)—C(14)—C(15)—H(15A)	−1.2 (1)
C(1)—N(1)—C(21)—H(21A)	−41.8 (1)	C(14)—C(15)—C(16)—C(17)	0.0 (1)
C(21)—N(1)—C(4)—C(3)	143.6 (1)	C(14)—C(15)—C(16)—H(16A)	−180.0 (1)
C(21)—N(1)—C(4)—C(5)	−97.9 (1)	H(15A)—C(15)—C(16)—C(17)	−179.9 (1)
C(4)—N(1)—C(21)—C(22)	78.9 (1)	H(15A)—C(15)—C(16)—H(16A)	0.2 (1)
C(21)—N(1)—C(4)—H(4A)	24.6 (1)	C(15)—C(16)—C(17)—C(18)	0.7 (1)
C(4)—N(1)—C(21)—H(21B)	−42.6 (1)	C(15)—C(16)—C(17)—H(17A)	−179.3 (1)
C(4)—N(1)—C(21)—H(21A)	−159.6 (1)	H(16A)—C(16)—C(17)—C(18)	−179.4 (1)
NI2+(1)—N(2)—C(5)—O(1)	−162.2 (1)	H(16A)—C(16)—C(17)—H(17A)	0.7 (1)
NI2+(1)—N(2)—C(5)—C(4)	21.7 (1)	C(16)—C(17)—C(18)—C(13)	−0.5 (1)
NI2+(1)—N(2)—C(6)—C(7)	−159.1 (1)	C(16)—C(17)—C(18)—H(18A)	179.5 (1)
NI2+(1)—N(2)—C(6)—C(11)	17.1 (1)	H(17A)—C(17)—C(18)—C(13)	179.5 (1)
C(6)—N(2)—C(5)—O(1)	15.6 (1)	H(17A)—C(17)—C(18)—H(18A)	−0.5 (1)
C(6)—N(2)—C(5)—C(4)	−160.6 (1)	N(3)—C(19)—C(20)—O(2)	10.6 (1)
C(5)—N(2)—C(6)—C(7)	23.4 (1)	N(3)—C(19)—C(20)—O(3)	−170.3 (1)
C(5)—N(2)—C(6)—C(11)	−160.4 (1)	N(3)—C(19)—H(19B)—H(19A)	−119.9 (1)
NI2+(1)—N(3)—C(12)—C(11)	11.2 (1)	N(3)—C(19)—H(19A)—H(19B)	119.9 (1)
NI2+(1)—N(3)—C(12)—C(13)	−169.6 (1)	H(19B)—C(19)—C(20)—O(2)	131.2 (1)
NI2+(1)—N(3)—C(19)—C(20)	−17.6 (1)	H(19B)—C(19)—C(20)—O(3)	−49.7 (1)
NI2+(1)—N(3)—C(19)—H(19B)	−138.2 (1)	C(20)—C(19)—H(19B)—H(19A)	119.7 (1)
NI2+(1)—N(3)—C(19)—H(19A)	102.9 (1)	H(19A)—C(19)—C(20)—O(2)	−109.9 (1)
C(19)—N(3)—C(12)—C(11)	179.8 (1)	H(19A)—C(19)—C(20)—O(3)	69.2 (1)
C(19)—N(3)—C(12)—C(13)	−1.0 (1)	C(20)—C(19)—H(19A)—H(19B)	−119.8 (1)
C(12)—N(3)—C(19)—C(20)	171.9 (1)	H(19B)—C(19)—H(19A)—H(19B)	0.0 (1)
C(12)—N(3)—C(19)—H(19B)	51.2 (1)	H(19A)—C(19)—H(19B)—H(19A)	0.0 (1)
C(12)—N(3)—C(19)—H(19A)	−67.7 (1)	N(1)—C(21)—C(22)—C(23)	104.5 (1)
N(1)—C(1)—C(2)—C(3)	42.2 (1)	N(1)—C(21)—C(22)—C(27)	−77.1 (1)
N(1)—C(1)—C(2)—H(2B)	−76.6 (1)	N(1)—C(21)—H(21B)—H(21A)	−117.7 (1)
N(1)—C(1)—C(2)—H(2A)	161.3 (1)	N(1)—C(21)—H(21A)—H(21B)	117.7 (1)
N(1)—C(1)—H(1B)—H(1A)	−123.1 (1)	H(21B)—C(21)—C(22)—C(23)	−134.1 (1)
N(1)—C(1)—H(1A)—H(1B)	123.1 (1)	H(21B)—C(21)—C(22)—C(27)	44.4 (1)
H(1B)—C(1)—C(2)—C(3)	161.4 (1)	C(22)—C(21)—H(21B)—H(21A)	117.7 (1)
C(2)—C(1)—H(1B)—H(1A)	122.8 (1)	H(21A)—C(21)—C(22)—C(23)	−17.1 (1)
H(1B)—C(1)—C(2)—H(2B)	42.5 (1)	H(21A)—C(21)—C(22)—C(27)	161.4 (1)
H(1B)—C(1)—C(2)—H(2A)	−79.5 (1)	C(22)—C(21)—H(21A)—H(21B)	−117.7 (1)
H(1A)—C(1)—C(2)—C(3)	−76.9 (1)	H(21B)—C(21)—H(21A)—H(21B)	0.0 (1)
C(2)—C(1)—H(1A)—H(1B)	−122.8 (1)	H(21A)—C(21)—H(21B)—H(21A)	0.0 (1)
H(1A)—C(1)—C(2)—H(2B)	164.2 (1)	C(21)—C(22)—C(23)—C(24)	178.5 (1)
H(1A)—C(1)—C(2)—H(2A)	42.2 (1)	C(21)—C(22)—C(23)—H(23A)	−1.2 (1)
H(1B)—C(1)—H(1A)—H(1B)	0.0 (1)	C(21)—C(22)—C(27)—C(26)	−179.4 (1)
H(1A)—C(1)—H(1B)—H(1A)	0.0 (1)	C(21)—C(22)—C(27)—H(27A)	0.7 (1)
C(1)—C(2)—C(3)—C(4)	−27.7 (1)	C(27)—C(22)—C(23)—C(24)	0.0 (1)
C(1)—C(2)—C(3)—H(3B)	−147.3 (1)	C(23)—C(22)—C(27)—C(26)	−0.9 (1)
C(1)—C(2)—C(3)—H(3A)	92.0 (1)	C(27)—C(22)—C(23)—H(23A)	−179.7 (1)
C(1)—C(2)—H(2B)—H(2A)	−123.2 (1)	C(23)—C(22)—C(27)—H(27A)	179.1 (1)
C(1)—C(2)—H(2A)—H(2B)	123.2 (1)	C(22)—C(23)—C(24)—C(25)	0.2 (1)
H(2B)—C(2)—C(3)—C(4)	91.2 (1)	C(22)—C(23)—C(24)—H(24A)	−179.8 (2)
C(3)—C(2)—H(2B)—H(2A)	123.2 (1)	H(23A)—C(23)—C(24)—C(25)	180.0 (2)
H(2B)—C(2)—C(3)—H(3B)	−28.4 (1)	H(23A)—C(23)—C(24)—H(24A)	−0.1 (1)
H(2B)—C(2)—C(3)—H(3A)	−149.1 (1)	C(23)—C(24)—C(25)—C(26)	0.4 (1)
H(2A)—C(2)—C(3)—C(4)	−146.8 (1)	C(23)—C(24)—C(25)—H(25A)	−179.8 (2)
C(3)—C(2)—H(2A)—H(2B)	−123.1 (1)	H(24A)—C(24)—C(25)—C(26)	−179.5 (2)
H(2A)—C(2)—C(3)—H(3B)	93.6 (1)	H(24A)—C(24)—C(25)—H(25A)	0.2 (2)
H(2A)—C(2)—C(3)—H(3A)	−27.1 (1)	C(24)—C(25)—C(26)—C(27)	−1.3 (1)
H(2B)—C(2)—H(2A)—H(2B)	0.0 (1)	C(24)—C(25)—C(26)—H(26A)	178.9 (2)
H(2A)—C(2)—H(2B)—H(2A)	0.0 (1)	H(25A)—C(25)—C(26)—C(27)	178.9 (2)
C(2)—C(3)—C(4)—N(1)	3.3 (1)	H(25A)—C(25)—C(26)—H(26A)	−0.8 (1)
C(2)—C(3)—C(4)—C(5)	−116.4 (1)	C(25)—C(26)—C(27)—C(22)	1.6 (1)
C(2)—C(3)—C(4)—H(4A)	122.2 (1)	C(25)—C(26)—C(27)—H(27A)	−178.5 (2)
C(2)—C(3)—H(3B)—H(3A)	−121.8 (1)	H(26A)—C(26)—C(27)—C(22)	−178.7 (2)
C(2)—C(3)—H(3A)—H(3B)	121.8 (1)	H(26A)—C(26)—C(27)—H(27A)	1.2 (1)
H(3B)—C(3)—C(4)—N(1)	122.8 (1)	C(1)—H(1B)—H(1A)—C(1)	0.0 (1)
H(3B)—C(3)—C(4)—C(5)	3.2 (1)	H(3A)ⁱ—H(1B)—C(1)—N(1)	−177.3 (1)
C(4)—C(3)—H(3B)—H(3A)	122.2 (1)	H(3A)ⁱ—H(1B)—C(1)—C(2)	68.6 (1)
H(3B)—C(3)—C(4)—H(4A)	−118.2 (1)	H(3A)ⁱ—H(1B)—C(1)—H(1A)	−54.2 (1)
H(3A)—C(3)—C(4)—N(1)	−116.3 (1)	H(3A)ⁱ—H(1B)—H(1A)—C(1)	143.9 (1)
H(3A)—C(3)—C(4)—C(5)	124.1 (1)	C(2)—H(2B)—H(2A)—C(2)	0.0 (1)
C(4)—C(3)—H(3A)—H(3B)	−122.1 (1)	C(3)—H(3B)—H(3A)—C(3)	0.0 (1)
H(3A)—C(3)—C(4)—H(4A)	2.7 (1)	H(1B)ⁱⁱ—H(3A)—C(3)—C(2)	50.2 (1)
H(3B)—C(3)—H(3A)—H(3B)	0.0 (1)	H(1B)ⁱⁱ—H(3A)—C(3)—C(4)	166.3 (1)
H(3A)—C(3)—H(3B)—H(3A)	0.0 (1)	H(1B)ⁱⁱ—H(3A)—C(3)—H(3B)	−71.6 (1)
N(1)—C(4)—C(5)—O(1)	155.4 (1)	H(1B)ⁱⁱ—H(3A)—H(3B)—C(3)	117.9 (1)
N(1)—C(4)—C(5)—N(2)	−28.1 (1)	C(19)—H(19B)—H(19A)—C(19)	0.0 (1)
C(3)—C(4)—C(5)—O(1)	−88.4 (1)	C(21)—H(21B)—H(21A)—C(21)	0.0 (1)
C(3)—C(4)—C(5)—N(2)	88.1 (1)

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

Experimental details

Crystal data
Chemical formula	C₂₇H₂₅NiN₃O₃
M_r	498.21
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	?
a, b, c (Å)	8.9817, 9.6588, 26.2593
V (Å³)	2278.06
Z	?
Radiation type	?, λ = ? Å
µ (mm⁻¹)	?
Crystal size (mm)	0.44 × 0.11 × 0.09

Data collection
Diffractometer	?
Absorption correction	–
No. of measured, independent and observed (?) reflections	?, ?, ?
R_int	?

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.032, 1.55
No. of reflections	26433
No. of parameters	905
Δρ_max, Δρ_min (e Å⁻³)	?, ?

Computer programs: Koritsanszky et al., (2003).

Selected geometric parameters (Å, º) top

NI2+(1)—O(2)	1.8620 (4)	C(12)—C(13)	1.4965 (4)
NI2+(1)—N(1)	1.9413 (3)	C(13)—C(14)	1.3987 (5)
NI2+(1)—N(2)	1.8559 (3)	C(13)—C(18)	1.3962 (5)
NI2+(1)—N(3)	1.8533 (3)	C(14)—C(15)	1.3950 (6)
O(1)—C(5)	1.2288 (5)	C(14)—H(14A)	1.0829 (1)
O(2)—C(20)	1.2933 (6)	C(15)—C(16)	1.3942 (7)
O(3)—C(20)	1.2249 (5)	C(15)—H(15A)	1.0839 (1)
N(1)—C(1)	1.4927 (5)	C(16)—C(17)	1.3939 (7)
N(1)—C(4)	1.4936 (4)	C(16)—H(16A)	1.0837 (1)
N(1)—C(21)	1.5000 (5)	C(17)—C(18)	1.3952 (5)
N(2)—C(5)	1.3750 (4)	C(17)—H(17A)	1.0824 (1)
N(2)—C(6)	1.3897 (4)	C(18)—H(18A)	1.0831 (1)
N(3)—C(12)	1.2982 (4)	C(19)—C(20)	1.5205 (6)
N(3)—C(19)	1.4691 (4)	C(19)—H(19B)	1.0926 (1)
C(1)—C(2)	1.5123 (6)	C(19)—H(19A)	1.0918 (1)
C(1)—H(1B)	1.0921 (1)	C(21)—C(22)	1.5067 (6)
C(1)—H(1A)	1.0903 (1)	C(21)—H(21B)	1.0916 (1)
C(2)—C(3)	1.5324 (6)	C(21)—H(21A)	1.0918 (1)
C(2)—H(2B)	1.0932 (1)	C(22)—C(23)	1.4006 (6)
C(2)—H(2A)	1.0897 (1)	C(22)—C(27)	1.3979 (7)
C(3)—C(4)	1.5555 (5)	C(23)—C(24)	1.3931 (9)
C(3)—H(3B)	1.0929 (1)	C(23)—H(23A)	1.0841 (1)
C(3)—H(3A)	1.0921 (1)	C(24)—C(25)	1.4024 (15)
C(4)—C(5)	1.5090 (5)	C(24)—H(24A)	1.0811 (1)
C(4)—H(4A)	1.0986 (1)	C(25)—C(26)	1.3953 (13)
C(6)—C(7)	1.4155 (4)	C(25)—H(25A)	1.0837 (1)
C(6)—C(11)	1.4213 (4)	C(26)—C(27)	1.3916 (8)
C(7)—C(8)	1.3807 (6)	C(26)—H(26A)	1.0851 (1)
C(7)—H(7A)	1.0832 (1)	C(27)—H(27A)	1.0845 (1)
C(8)—C(9)	1.3968 (6)	H(1B)—H(1A)	1.7791 (1)
C(8)—H(8A)	1.0824 (1)	H(1B)—H(3A)ⁱ	2.0658 (5)
C(9)—C(10)	1.3815 (5)	H(2B)—H(2A)	1.7798 (1)
C(9)—H(9A)	1.0826 (1)	H(3B)—H(3A)	1.7762 (1)
C(10)—C(11)	1.4154 (5)	H(19B)—H(19A)	1.7697 (1)
C(10)—H(10A)	1.0846 (1)	H(21B)—H(21A)	1.7629 (1)
C(11)—C(12)	1.4606 (4)

O(2)—NI2+(1)—N(1)	89.031 (16)	C(11)—C(12)—C(13)	117.86 (3)
O(2)—NI2+(1)—N(2)	175.892 (19)	C(12)—C(13)—C(14)	119.67 (3)
O(2)—NI2+(1)—N(3)	87.348 (16)	C(12)—C(13)—C(18)	120.55 (3)
N(1)—NI2+(1)—N(2)	88.659 (13)	C(14)—C(13)—C(18)	119.77 (3)
N(1)—NI2+(1)—N(3)	168.551 (14)	C(13)—C(14)—C(15)	119.93 (4)
N(2)—NI2+(1)—N(3)	95.556 (14)	C(13)—C(14)—H(14A)	120.04 (2)
NI2+(1)—O(2)—C(20)	115.31 (3)	C(15)—C(14)—H(14A)	120.03 (3)
NI2+(1)—N(1)—C(1)	113.02 (3)	C(14)—C(15)—C(16)	120.13 (4)
NI2+(1)—N(1)—C(4)	107.52 (2)	C(14)—C(15)—H(15A)	119.95 (3)
NI2+(1)—N(1)—C(21)	107.28 (2)	C(16)—C(15)—H(15A)	119.92 (2)
C(1)—N(1)—C(4)	105.17 (3)	C(15)—C(16)—C(17)	120.03 (4)
C(1)—N(1)—C(21)	110.16 (3)	C(15)—C(16)—H(16A)	120.11 (2)
C(4)—N(1)—C(21)	113.79 (3)	C(17)—C(16)—H(16A)	119.86 (2)
NI2+(1)—N(2)—C(5)	114.05 (2)	C(16)—C(17)—C(18)	119.94 (4)
NI2+(1)—N(2)—C(6)	125.16 (2)	C(16)—C(17)—H(17A)	120.16 (2)
C(5)—N(2)—C(6)	120.74 (3)	C(18)—C(17)—H(17A)	119.90 (3)
NI2+(1)—N(3)—C(12)	128.62 (2)	C(13)—C(18)—C(17)	120.18 (4)
NI2+(1)—N(3)—C(19)	110.42 (2)	C(13)—C(18)—H(18A)	119.91 (2)
C(12)—N(3)—C(19)	120.14 (3)	C(17)—C(18)—H(18A)	119.90 (3)
N(1)—C(1)—C(2)	103.08 (3)	N(3)—C(19)—C(20)	109.44 (3)
N(1)—C(1)—H(1B)	111.189 (19)	N(3)—C(19)—H(19B)	109.83 (2)
N(1)—C(1)—H(1A)	111.19 (2)	N(3)—C(19)—H(19A)	109.81 (2)
C(2)—C(1)—H(1B)	111.03 (2)	C(20)—C(19)—H(19B)	109.82 (2)
C(2)—C(1)—H(1A)	111.05 (2)	C(20)—C(19)—H(19A)	109.70 (2)
H(1B)—C(1)—H(1A)	109.2119 (1)	H(19B)—C(19)—H(19A)	108.2273 (1)
C(1)—C(2)—C(3)	102.54 (3)	O(2)—C(20)—O(3)	124.89 (5)
C(1)—C(2)—H(2B)	111.18 (2)	O(2)—C(20)—C(19)	114.52 (3)
C(1)—C(2)—H(2A)	111.30 (2)	O(3)—C(20)—C(19)	120.59 (4)
C(3)—C(2)—H(2B)	111.17 (3)	N(1)—C(21)—C(22)	113.95 (3)
C(3)—C(2)—H(2A)	111.30 (2)	N(1)—C(21)—H(21B)	108.728 (19)
H(2B)—C(2)—H(2A)	109.2410 (1)	N(1)—C(21)—H(21A)	108.81 (2)
C(2)—C(3)—C(4)	104.96 (3)	C(22)—C(21)—H(21B)	108.75 (2)
C(2)—C(3)—H(3B)	110.71 (3)	C(22)—C(21)—H(21A)	108.74 (2)
C(2)—C(3)—H(3A)	110.67 (2)	H(21B)—C(21)—H(21A)	107.6897 (1)
C(4)—C(3)—H(3B)	110.80 (2)	C(21)—C(22)—C(23)	119.80 (4)
C(4)—C(3)—H(3A)	110.91 (2)	C(21)—C(22)—C(27)	121.13 (4)
H(3B)—C(3)—H(3A)	108.7679 (1)	C(23)—C(22)—C(27)	119.05 (5)
N(1)—C(4)—C(3)	105.54 (3)	C(22)—C(23)—C(24)	120.74 (6)
N(1)—C(4)—C(5)	111.16 (3)	C(22)—C(23)—H(23A)	119.80 (3)
N(1)—C(4)—H(4A)	110.168 (18)	C(24)—C(23)—H(23A)	119.46 (4)
C(3)—C(4)—C(5)	109.39 (3)	C(23)—C(24)—C(25)	119.66 (6)
C(3)—C(4)—H(4A)	110.23 (2)	C(23)—C(24)—H(24A)	120.38 (4)
C(5)—C(4)—H(4A)	110.240 (19)	C(25)—C(24)—H(24A)	119.96 (4)
O(1)—C(5)—N(2)	127.80 (4)	C(24)—C(25)—C(26)	119.83 (6)
O(1)—C(5)—C(4)	119.72 (3)	C(24)—C(25)—H(25A)	120.05 (4)
N(2)—C(5)—C(4)	112.38 (3)	C(26)—C(25)—H(25A)	120.11 (5)
N(2)—C(6)—C(7)	120.61 (3)	C(25)—C(26)—C(27)	120.12 (7)
N(2)—C(6)—C(11)	121.79 (3)	C(25)—C(26)—H(26A)	119.87 (5)
C(7)—C(6)—C(11)	117.49 (3)	C(27)—C(26)—H(26A)	120.00 (4)
C(6)—C(7)—C(8)	121.76 (3)	C(22)—C(27)—C(26)	120.58 (6)
C(6)—C(7)—H(7A)	119.10 (2)	C(22)—C(27)—H(27A)	119.62 (3)
C(8)—C(7)—H(7A)	119.14 (2)	C(26)—C(27)—H(27A)	119.80 (4)
C(7)—C(8)—C(9)	120.85 (3)	C(1)—H(1B)—H(1A)	35.3615 (1)
C(7)—C(8)—H(8A)	119.57 (2)	C(1)—H(1B)—H(3A)ⁱ	137.700 (16)
C(9)—C(8)—H(8A)	119.58 (2)	H(1A)—H(1B)—H(3A)ⁱ	112.040 (17)
C(8)—C(9)—C(10)	118.63 (4)	C(1)—H(1A)—H(1B)	35.4267 (1)
C(8)—C(9)—H(9A)	120.69 (2)	C(2)—H(2B)—H(2A)	35.3154 (1)
C(10)—C(9)—H(9A)	120.68 (2)	C(2)—H(2A)—H(2B)	35.4437 (1)
C(9)—C(10)—C(11)	121.95 (3)	C(3)—H(3B)—H(3A)	35.6002 (1)
C(9)—C(10)—H(10A)	119.01 (2)	C(3)—H(3A)—H(1B)ⁱⁱ	112.945 (17)
C(11)—C(10)—H(10A)	119.04 (2)	C(3)—H(3A)—H(3B)	35.6319 (1)
C(6)—C(11)—C(10)	119.26 (3)	H(1B)ⁱⁱ—H(3A)—H(3B)	98.488 (18)
C(6)—C(11)—C(12)	123.65 (3)	C(19)—H(19B)—H(19A)	35.8723 (1)
C(10)—C(11)—C(12)	117.06 (3)	C(19)—H(19A)—H(19B)	35.9004 (1)
N(3)—C(12)—C(11)	122.05 (3)	C(21)—H(21B)—H(21A)	36.1575 (1)
N(3)—C(12)—C(13)	120.08 (3)	C(21)—H(21A)—H(21B)	36.1528 (1)

O(2)—NI2+(1)—N(1)—C(1)	53.0 (1)	H(4A)—C(4)—C(5)—O(1)	32.9 (1)
O(2)—NI2+(1)—N(1)—C(4)	168.6 (1)	H(4A)—C(4)—C(5)—N(2)	−150.5 (1)
N(1)—NI2+(1)—O(2)—C(20)	159.1 (1)	N(2)—C(6)—C(7)—C(8)	178.0 (1)
O(2)—NI2+(1)—N(1)—C(21)	−68.6 (1)	N(2)—C(6)—C(7)—H(7A)	−2.0 (1)
O(2)—NI2+(1)—N(2)—C(5)	−63.6 (3)	N(2)—C(6)—C(11)—C(10)	−179.0 (1)
O(2)—NI2+(1)—N(2)—C(6)	118.8 (3)	N(2)—C(6)—C(11)—C(12)	−1.1 (1)
N(2)—NI2+(1)—O(2)—C(20)	−145.1 (3)	C(11)—C(6)—C(7)—C(8)	1.5 (1)
O(2)—NI2+(1)—N(3)—C(12)	−175.0 (1)	C(7)—C(6)—C(11)—C(10)	−2.6 (1)
O(2)—NI2+(1)—N(3)—C(19)	15.5 (1)	C(7)—C(6)—C(11)—C(12)	175.3 (1)
N(3)—NI2+(1)—O(2)—C(20)	−10.0 (1)	C(11)—C(6)—C(7)—H(7A)	−178.4 (1)
N(2)—NI2+(1)—N(1)—C(1)	−123.6 (1)	C(6)—C(7)—C(8)—C(9)	0.6 (1)
N(2)—NI2+(1)—N(1)—C(4)	−8.0 (1)	C(6)—C(7)—C(8)—H(8A)	−179.4 (1)
N(1)—NI2+(1)—N(2)—C(5)	−7.8 (1)	H(7A)—C(7)—C(8)—C(9)	−179.5 (1)
N(1)—NI2+(1)—N(2)—C(6)	174.6 (1)	H(7A)—C(7)—C(8)—H(8A)	0.6 (1)
N(2)—NI2+(1)—N(1)—C(21)	114.8 (1)	C(7)—C(8)—C(9)—C(10)	−1.6 (1)
N(3)—NI2+(1)—N(1)—C(1)	124.5 (1)	C(7)—C(8)—C(9)—H(9A)	178.3 (1)
N(3)—NI2+(1)—N(1)—C(4)	−119.8 (1)	H(8A)—C(8)—C(9)—C(10)	178.4 (1)
N(1)—NI2+(1)—N(3)—C(12)	113.3 (1)	H(8A)—C(8)—C(9)—H(9A)	−1.8 (1)
N(1)—NI2+(1)—N(3)—C(19)	−56.2 (1)	C(8)—C(9)—C(10)—C(11)	0.5 (1)
N(3)—NI2+(1)—N(1)—C(21)	2.9 (1)	C(8)—C(9)—C(10)—H(10A)	−179.5 (1)
N(3)—NI2+(1)—N(2)—C(5)	161.6 (1)	H(9A)—C(9)—C(10)—C(11)	−179.4 (1)
N(3)—NI2+(1)—N(2)—C(6)	−16.1 (1)	H(9A)—C(9)—C(10)—H(10A)	0.6 (1)
N(2)—NI2+(1)—N(3)—C(12)	2.1 (1)	C(9)—C(10)—C(11)—C(6)	1.7 (1)
N(2)—NI2+(1)—N(3)—C(19)	−167.4 (1)	C(9)—C(10)—C(11)—C(12)	−176.4 (1)
NI2+(1)—O(2)—C(20)—O(3)	−177.4 (1)	H(10A)—C(10)—C(11)—C(6)	−178.3 (1)
NI2+(1)—O(2)—C(20)—C(19)	1.6 (1)	H(10A)—C(10)—C(11)—C(12)	3.6 (1)
NI2+(1)—N(1)—C(1)—C(2)	76.0 (1)	C(6)—C(11)—C(12)—N(3)	−13.6 (1)
NI2+(1)—N(1)—C(1)—H(1B)	−43.0 (1)	C(6)—C(11)—C(12)—C(13)	167.2 (1)
NI2+(1)—N(1)—C(1)—H(1A)	−165.0 (1)	C(10)—C(11)—C(12)—N(3)	164.4 (1)
NI2+(1)—N(1)—C(4)—C(3)	−97.7 (1)	C(10)—C(11)—C(12)—C(13)	−14.9 (1)
NI2+(1)—N(1)—C(4)—C(5)	20.8 (1)	N(3)—C(12)—C(13)—C(14)	103.1 (1)
NI2+(1)—N(1)—C(4)—H(4A)	143.3 (1)	N(3)—C(12)—C(13)—C(18)	−77.8 (1)
NI2+(1)—N(1)—C(21)—C(22)	−39.9 (1)	C(11)—C(12)—C(13)—C(14)	−77.6 (1)
NI2+(1)—N(1)—C(21)—H(21B)	−161.4 (1)	C(11)—C(12)—C(13)—C(18)	101.4 (1)
NI2+(1)—N(1)—C(21)—H(21A)	81.6 (1)	C(12)—C(13)—C(14)—C(15)	−179.9 (1)
C(4)—N(1)—C(1)—C(2)	−41.0 (1)	C(12)—C(13)—C(14)—H(14A)	0.3 (1)
C(1)—N(1)—C(4)—C(3)	23.0 (1)	C(12)—C(13)—C(18)—C(17)	−179.4 (1)
C(1)—N(1)—C(4)—C(5)	141.5 (1)	C(12)—C(13)—C(18)—H(18A)	0.6 (1)
C(4)—N(1)—C(1)—H(1B)	−160.0 (1)	C(18)—C(13)—C(14)—C(15)	1.0 (1)
C(4)—N(1)—C(1)—H(1A)	78.0 (1)	C(14)—C(13)—C(18)—C(17)	−0.3 (1)
C(1)—N(1)—C(4)—H(4A)	−96.0 (1)	C(18)—C(13)—C(14)—H(14A)	−178.8 (1)
C(21)—N(1)—C(1)—C(2)	−164.0 (1)	C(14)—C(13)—C(18)—H(18A)	179.7 (1)
C(1)—N(1)—C(21)—C(22)	−163.3 (1)	C(13)—C(14)—C(15)—C(16)	−0.9 (1)
C(21)—N(1)—C(1)—H(1B)	77.0 (1)	C(13)—C(14)—C(15)—H(15A)	179.0 (1)
C(21)—N(1)—C(1)—H(1A)	−45.0 (1)	H(14A)—C(14)—C(15)—C(16)	179.0 (1)
C(1)—N(1)—C(21)—H(21B)	75.3 (1)	H(14A)—C(14)—C(15)—H(15A)	−1.2 (1)
C(1)—N(1)—C(21)—H(21A)	−41.8 (1)	C(14)—C(15)—C(16)—C(17)	0.0 (1)
C(21)—N(1)—C(4)—C(3)	143.6 (1)	C(14)—C(15)—C(16)—H(16A)	−180.0 (1)
C(21)—N(1)—C(4)—C(5)	−97.9 (1)	H(15A)—C(15)—C(16)—C(17)	−179.9 (1)
C(4)—N(1)—C(21)—C(22)	78.9 (1)	H(15A)—C(15)—C(16)—H(16A)	0.2 (1)
C(21)—N(1)—C(4)—H(4A)	24.6 (1)	C(15)—C(16)—C(17)—C(18)	0.7 (1)
C(4)—N(1)—C(21)—H(21B)	−42.6 (1)	C(15)—C(16)—C(17)—H(17A)	−179.3 (1)
C(4)—N(1)—C(21)—H(21A)	−159.6 (1)	H(16A)—C(16)—C(17)—C(18)	−179.4 (1)
NI2+(1)—N(2)—C(5)—O(1)	−162.2 (1)	H(16A)—C(16)—C(17)—H(17A)	0.7 (1)
NI2+(1)—N(2)—C(5)—C(4)	21.7 (1)	C(16)—C(17)—C(18)—C(13)	−0.5 (1)
NI2+(1)—N(2)—C(6)—C(7)	−159.1 (1)	C(16)—C(17)—C(18)—H(18A)	179.5 (1)
NI2+(1)—N(2)—C(6)—C(11)	17.1 (1)	H(17A)—C(17)—C(18)—C(13)	179.5 (1)
C(6)—N(2)—C(5)—O(1)	15.6 (1)	H(17A)—C(17)—C(18)—H(18A)	−0.5 (1)
C(6)—N(2)—C(5)—C(4)	−160.6 (1)	N(3)—C(19)—C(20)—O(2)	10.6 (1)
C(5)—N(2)—C(6)—C(7)	23.4 (1)	N(3)—C(19)—C(20)—O(3)	−170.3 (1)
C(5)—N(2)—C(6)—C(11)	−160.4 (1)	N(3)—C(19)—H(19B)—H(19A)	−119.9 (1)
NI2+(1)—N(3)—C(12)—C(11)	11.2 (1)	N(3)—C(19)—H(19A)—H(19B)	119.9 (1)
NI2+(1)—N(3)—C(12)—C(13)	−169.6 (1)	H(19B)—C(19)—C(20)—O(2)	131.2 (1)
NI2+(1)—N(3)—C(19)—C(20)	−17.6 (1)	H(19B)—C(19)—C(20)—O(3)	−49.7 (1)
NI2+(1)—N(3)—C(19)—H(19B)	−138.2 (1)	C(20)—C(19)—H(19B)—H(19A)	119.7 (1)
NI2+(1)—N(3)—C(19)—H(19A)	102.9 (1)	H(19A)—C(19)—C(20)—O(2)	−109.9 (1)
C(19)—N(3)—C(12)—C(11)	179.8 (1)	H(19A)—C(19)—C(20)—O(3)	69.2 (1)
C(19)—N(3)—C(12)—C(13)	−1.0 (1)	C(20)—C(19)—H(19A)—H(19B)	−119.8 (1)
C(12)—N(3)—C(19)—C(20)	171.9 (1)	H(19B)—C(19)—H(19A)—H(19B)	0.0 (1)
C(12)—N(3)—C(19)—H(19B)	51.2 (1)	H(19A)—C(19)—H(19B)—H(19A)	0.0 (1)
C(12)—N(3)—C(19)—H(19A)	−67.7 (1)	N(1)—C(21)—C(22)—C(23)	104.5 (1)
N(1)—C(1)—C(2)—C(3)	42.2 (1)	N(1)—C(21)—C(22)—C(27)	−77.1 (1)
N(1)—C(1)—C(2)—H(2B)	−76.6 (1)	N(1)—C(21)—H(21B)—H(21A)	−117.7 (1)
N(1)—C(1)—C(2)—H(2A)	161.3 (1)	N(1)—C(21)—H(21A)—H(21B)	117.7 (1)
N(1)—C(1)—H(1B)—H(1A)	−123.1 (1)	H(21B)—C(21)—C(22)—C(23)	−134.1 (1)
N(1)—C(1)—H(1A)—H(1B)	123.1 (1)	H(21B)—C(21)—C(22)—C(27)	44.4 (1)
H(1B)—C(1)—C(2)—C(3)	161.4 (1)	C(22)—C(21)—H(21B)—H(21A)	117.7 (1)
C(2)—C(1)—H(1B)—H(1A)	122.8 (1)	H(21A)—C(21)—C(22)—C(23)	−17.1 (1)
H(1B)—C(1)—C(2)—H(2B)	42.5 (1)	H(21A)—C(21)—C(22)—C(27)	161.4 (1)
H(1B)—C(1)—C(2)—H(2A)	−79.5 (1)	C(22)—C(21)—H(21A)—H(21B)	−117.7 (1)
H(1A)—C(1)—C(2)—C(3)	−76.9 (1)	H(21B)—C(21)—H(21A)—H(21B)	0.0 (1)
C(2)—C(1)—H(1A)—H(1B)	−122.8 (1)	H(21A)—C(21)—H(21B)—H(21A)	0.0 (1)
H(1A)—C(1)—C(2)—H(2B)	164.2 (1)	C(21)—C(22)—C(23)—C(24)	178.5 (1)
H(1A)—C(1)—C(2)—H(2A)	42.2 (1)	C(21)—C(22)—C(23)—H(23A)	−1.2 (1)
H(1B)—C(1)—H(1A)—H(1B)	0.0 (1)	C(21)—C(22)—C(27)—C(26)	−179.4 (1)
H(1A)—C(1)—H(1B)—H(1A)	0.0 (1)	C(21)—C(22)—C(27)—H(27A)	0.7 (1)
C(1)—C(2)—C(3)—C(4)	−27.7 (1)	C(27)—C(22)—C(23)—C(24)	0.0 (1)
C(1)—C(2)—C(3)—H(3B)	−147.3 (1)	C(23)—C(22)—C(27)—C(26)	−0.9 (1)
C(1)—C(2)—C(3)—H(3A)	92.0 (1)	C(27)—C(22)—C(23)—H(23A)	−179.7 (1)
C(1)—C(2)—H(2B)—H(2A)	−123.2 (1)	C(23)—C(22)—C(27)—H(27A)	179.1 (1)
C(1)—C(2)—H(2A)—H(2B)	123.2 (1)	C(22)—C(23)—C(24)—C(25)	0.2 (1)
H(2B)—C(2)—C(3)—C(4)	91.2 (1)	C(22)—C(23)—C(24)—H(24A)	−179.8 (2)
C(3)—C(2)—H(2B)—H(2A)	123.2 (1)	H(23A)—C(23)—C(24)—C(25)	180.0 (2)
H(2B)—C(2)—C(3)—H(3B)	−28.4 (1)	H(23A)—C(23)—C(24)—H(24A)	−0.1 (1)
H(2B)—C(2)—C(3)—H(3A)	−149.1 (1)	C(23)—C(24)—C(25)—C(26)	0.4 (1)
H(2A)—C(2)—C(3)—C(4)	−146.8 (1)	C(23)—C(24)—C(25)—H(25A)	−179.8 (2)
C(3)—C(2)—H(2A)—H(2B)	−123.1 (1)	H(24A)—C(24)—C(25)—C(26)	−179.5 (2)
H(2A)—C(2)—C(3)—H(3B)	93.6 (1)	H(24A)—C(24)—C(25)—H(25A)	0.2 (2)
H(2A)—C(2)—C(3)—H(3A)	−27.1 (1)	C(24)—C(25)—C(26)—C(27)	−1.3 (1)
H(2B)—C(2)—H(2A)—H(2B)	0.0 (1)	C(24)—C(25)—C(26)—H(26A)	178.9 (2)
H(2A)—C(2)—H(2B)—H(2A)	0.0 (1)	H(25A)—C(25)—C(26)—C(27)	178.9 (2)
C(2)—C(3)—C(4)—N(1)	3.3 (1)	H(25A)—C(25)—C(26)—H(26A)	−0.8 (1)
C(2)—C(3)—C(4)—C(5)	−116.4 (1)	C(25)—C(26)—C(27)—C(22)	1.6 (1)
C(2)—C(3)—C(4)—H(4A)	122.2 (1)	C(25)—C(26)—C(27)—H(27A)	−178.5 (2)
C(2)—C(3)—H(3B)—H(3A)	−121.8 (1)	H(26A)—C(26)—C(27)—C(22)	−178.7 (2)
C(2)—C(3)—H(3A)—H(3B)	121.8 (1)	H(26A)—C(26)—C(27)—H(27A)	1.2 (1)
H(3B)—C(3)—C(4)—N(1)	122.8 (1)	C(1)—H(1B)—H(1A)—C(1)	0.0 (1)
H(3B)—C(3)—C(4)—C(5)	3.2 (1)	H(3A)ⁱ—H(1B)—C(1)—N(1)	−177.3 (1)
C(4)—C(3)—H(3B)—H(3A)	122.2 (1)	H(3A)ⁱ—H(1B)—C(1)—C(2)	68.6 (1)
H(3B)—C(3)—C(4)—H(4A)	−118.2 (1)	H(3A)ⁱ—H(1B)—C(1)—H(1A)	−54.2 (1)
H(3A)—C(3)—C(4)—N(1)	−116.3 (1)	H(3A)ⁱ—H(1B)—H(1A)—C(1)	143.9 (1)
H(3A)—C(3)—C(4)—C(5)	124.1 (1)	C(2)—H(2B)—H(2A)—C(2)	0.0 (1)
C(4)—C(3)—H(3A)—H(3B)	−122.1 (1)	C(3)—H(3B)—H(3A)—C(3)	0.0 (1)
H(3A)—C(3)—C(4)—H(4A)	2.7 (1)	H(1B)ⁱⁱ—H(3A)—C(3)—C(2)	50.2 (1)
H(3B)—C(3)—H(3A)—H(3B)	0.0 (1)	H(1B)ⁱⁱ—H(3A)—C(3)—C(4)	166.3 (1)
H(3A)—C(3)—H(3B)—H(3A)	0.0 (1)	H(1B)ⁱⁱ—H(3A)—C(3)—H(3B)	−71.6 (1)
N(1)—C(4)—C(5)—O(1)	155.4 (1)	H(1B)ⁱⁱ—H(3A)—H(3B)—C(3)	117.9 (1)
N(1)—C(4)—C(5)—N(2)	−28.1 (1)	C(19)—H(19B)—H(19A)—C(19)	0.0 (1)
C(3)—C(4)—C(5)—O(1)	−88.4 (1)	C(21)—H(21B)—H(21A)—C(21)	0.0 (1)
C(3)—C(4)—C(5)—N(2)	88.1 (1)

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

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