Trichloridotris{N-[phen-yl(pyridin-2-yl)methyl-idene]hydroxyl-amine-κ(2)N,N'}neodymium(III).

In the title compound, [NdCl(3)(C(12)H(10)N(2)O)(3)], the central Nd(III) ion is nine-coordinated by six N atoms from three bidentate chelate N-[phen-yl(pyridin-2-yl)methyl-idene]hydroxyl-amine ligands and three Cl(-) ions, and displays a distorted tricapped trigonal prismatic geometry. The complex mol-ecules are stabilized by intra-molecular O-H⋯Cl hydrogen bonds.

Related literature

For complexes of oximes, see: Kukushkin & Pombeiro (1999 ▶); Milios et al. (2007 ▶); Fritsky et al. (2004 ▶); Xu et al. (2007 ▶); Papatriantafyllopoulou et al. (2009 ▶). For 3d-n class="Chemical">metal complexes of N-[phen­yl(pyridine-2-yl)methyl­idene]hydroxyl­amine, see: Milios et al. (2003 ▶); Milios et al. (2004 ▶). For an Sm complex with this ligand, see: Lei et al. (2012 ▶).

Experimental

Crystal data

[NdCl3(C12n class="Species">H10N2O)3]

M = 845.25

Triclinic,

a = 8.6367 (17) Å

b = 10.460 (2) Å

c = 19.847 (4) Å

α = 91.87 (3)°

β = 94.38 (3)°

γ = 92.80 (3)°

V = 1784.4 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.72 mm−1

T = 293 K

0.31 × 0.18 × 0.13 mm

Data collection

Bruker SMART CCD-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.617, T max = 0.807

30524 measured reflections

7775 independent reflections

7155 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.059

S = 1.04

7775 reflections

445 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014055/zs2190sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014055/zs2190Isup2.hkl

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

[NdCl3(C12H10N2O)3]	Z = 2
Mr = 845.25	F(000) = 846
Triclinic, P1	char
Hall symbol: -P 1	Dx = 1.573 Mg m−3
a = 8.6367 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.460 (2) Å	Cell parameters from 7737 reflections
c = 19.847 (4) Å	θ = 2.2–27.0°
α = 91.87 (3)°	µ = 1.72 mm−1
β = 94.38 (3)°	T = 293 K
γ = 92.80 (3)°	Block, colourless
V = 1784.4 (6) Å3	0.31 × 0.18 × 0.13 mm

Bruker SMART CCD-detector diffractometer	7775 independent reflections
Radiation source: fine-focus sealed tube	7155 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 27.0°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.617, Tmax = 0.807	k = −13→13
30524 measured reflections	l = −25→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0316P)2 + 0.3895P] where P = (Fo2 + 2Fc2)/3
7775 reflections	(Δ/σ)max = 0.002
445 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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
Nd1	0.170030 (12)	0.594157 (10)	0.248609 (5)	0.03370 (4)
Cl2	0.10720 (8)	0.35456 (5)	0.30113 (3)	0.05379 (15)
Cl1	0.27975 (7)	0.70288 (6)	0.13140 (3)	0.05048 (14)
Cl3	0.48680 (7)	0.57109 (6)	0.27455 (3)	0.05349 (15)
N2	0.2436 (2)	0.41331 (18)	0.16542 (10)	0.0429 (4)
N6	0.2375 (2)	0.61037 (18)	0.38390 (9)	0.0437 (4)
N1	−0.0455 (2)	0.48814 (17)	0.15808 (9)	0.0397 (4)
N3	−0.0819 (2)	0.65372 (18)	0.31740 (9)	0.0415 (4)
N5	0.2564 (2)	0.81945 (17)	0.31196 (10)	0.0434 (4)
C27	0.3334 (5)	1.0579 (3)	0.37346 (19)	0.0884 (11)
H27	0.3572	1.1381	0.3943	0.106*
N4	−0.0185 (2)	0.77901 (18)	0.20749 (9)	0.0418 (4)
C7	0.2007 (3)	0.2515 (2)	0.07372 (11)	0.0416 (5)
C18	−0.1209 (2)	0.8276 (2)	0.24228 (11)	0.0378 (4)
O1	0.3882 (2)	0.36271 (19)	0.17316 (10)	0.0627 (5)
H1A	0.4419	0.4034	0.2031	0.094*
O2	−0.0065 (2)	0.83670 (19)	0.14624 (9)	0.0592 (5)
H2A	0.0687	0.8104	0.1282	0.089*
C19	−0.2129 (3)	0.9365 (2)	0.21929 (11)	0.0397 (5)
C5	−0.0047 (3)	0.4056 (2)	0.10935 (11)	0.0394 (5)
O3	0.2290 (2)	0.50316 (16)	0.42307 (8)	0.0576 (4)
H3A	0.2028	0.4398	0.3987	0.086*
C17	−0.1480 (2)	0.7670 (2)	0.30694 (11)	0.0384 (5)
C13	−0.1152 (3)	0.5941 (2)	0.37345 (13)	0.0502 (6)
H13	−0.0759	0.5139	0.3803	0.060*
C31	0.2881 (3)	0.7204 (3)	0.49380 (12)	0.0508 (6)
C6	0.1547 (3)	0.3581 (2)	0.11766 (11)	0.0399 (5)
C21	−0.2296 (4)	1.1591 (3)	0.19732 (14)	0.0624 (7)
H21	−0.1853	1.2421	0.1996	0.075*
C1	−0.1928 (3)	0.5235 (2)	0.15376 (12)	0.0459 (5)
H1	−0.2241	0.5772	0.1879	0.055*
C4	−0.1058 (3)	0.3652 (3)	0.05469 (12)	0.0521 (6)
H4	−0.0734	0.3112	0.0210	0.063*
C30	0.2678 (3)	0.7144 (2)	0.41872 (11)	0.0440 (5)
C24	−0.3642 (3)	0.9139 (3)	0.19283 (13)	0.0512 (6)
H24	−0.4110	0.8319	0.1923	0.061*
C14	−0.2040 (3)	0.6440 (3)	0.42155 (13)	0.0569 (6)
H14	−0.2222	0.5994	0.4602	0.068*
C25	0.2728 (3)	0.9250 (2)	0.27624 (14)	0.0537 (6)
H25	0.2582	0.9167	0.2294	0.064*
C20	−0.1452 (3)	1.0601 (2)	0.22234 (13)	0.0516 (6)
H20	−0.0437	1.0759	0.2411	0.062*
C29	0.2820 (3)	0.8323 (2)	0.37946 (12)	0.0475 (5)
C23	−0.4461 (3)	1.0143 (3)	0.16705 (14)	0.0630 (7)
H23	−0.5476	0.9994	0.1482	0.076*
C32	0.4105 (3)	0.6620 (3)	0.52790 (13)	0.0559 (6)
H32	0.4837	0.6224	0.5036	0.067*
C16	−0.2384 (3)	0.8229 (2)	0.35265 (13)	0.0516 (6)
H16	−0.2810	0.9013	0.3441	0.062*
C33	0.4240 (4)	0.6624 (3)	0.59736 (15)	0.0744 (9)
H33	0.5055	0.6222	0.6199	0.089*
C11	0.1861 (4)	0.0299 (3)	0.03858 (14)	0.0635 (7)
H11	0.1448	−0.0530	0.0427	0.076*
C12	0.1387 (3)	0.1293 (2)	0.07905 (13)	0.0549 (6)
H12	0.0648	0.1129	0.1098	0.066*
C2	−0.3004 (3)	0.4845 (3)	0.10144 (14)	0.0554 (6)
H2	−0.4018	0.5110	0.1006	0.067*
C22	−0.3780 (4)	1.1357 (3)	0.16916 (14)	0.0676 (8)
H22	−0.4332	1.2026	0.1513	0.081*
C8	0.3121 (3)	0.2733 (3)	0.02820 (14)	0.0605 (7)
H8	0.3573	0.3552	0.0250	0.073*
C9	0.3564 (4)	0.1743 (3)	−0.01235 (15)	0.0738 (9)
H9	0.4298	0.1897	−0.0434	0.089*
C3	−0.2561 (3)	0.4062 (3)	0.05076 (14)	0.0612 (7)
H3	−0.3258	0.3808	0.0142	0.073*
C15	−0.2652 (3)	0.7611 (3)	0.41137 (14)	0.0597 (7)
H15	−0.3238	0.7982	0.4435	0.072*
C35	0.1970 (5)	0.7814 (4)	0.60097 (17)	0.0867 (11)
H35	0.1257	0.8220	0.6260	0.104*
C26	0.3100 (4)	1.0446 (3)	0.30484 (18)	0.0729 (8)
H26	0.3191	1.1153	0.2780	0.087*
C10	0.2927 (4)	0.0537 (3)	−0.00695 (14)	0.0663 (8)
H10	0.3223	−0.0128	−0.0346	0.080*
C36	0.1811 (4)	0.7812 (3)	0.53085 (15)	0.0708 (8)
H36	0.0992	0.8216	0.5088	0.085*
C34	0.3174 (5)	0.7219 (4)	0.63336 (16)	0.0888 (12)
H34	0.3270	0.7220	0.6803	0.107*
C28	0.3211 (4)	0.9497 (3)	0.41152 (16)	0.0735 (9)
H28	0.3391	0.9562	0.4583	0.088*

	U11	U22	U33	U12	U13	U23
Nd1	0.03692 (7)	0.02906 (7)	0.03506 (7)	0.00424 (4)	0.00134 (4)	−0.00019 (4)
Cl2	0.0757 (4)	0.0322 (3)	0.0531 (3)	−0.0011 (3)	0.0043 (3)	0.0023 (2)
Cl1	0.0546 (3)	0.0522 (3)	0.0471 (3)	0.0083 (3)	0.0152 (3)	0.0057 (3)
Cl3	0.0391 (3)	0.0638 (4)	0.0559 (3)	0.0057 (3)	−0.0057 (2)	−0.0067 (3)
N2	0.0381 (9)	0.0402 (10)	0.0505 (11)	0.0122 (8)	0.0013 (8)	−0.0055 (8)
N6	0.0537 (11)	0.0375 (10)	0.0399 (10)	0.0020 (8)	0.0022 (8)	0.0021 (8)
N1	0.0399 (9)	0.0357 (10)	0.0434 (10)	0.0052 (8)	0.0020 (8)	−0.0007 (8)
N3	0.0434 (10)	0.0372 (10)	0.0449 (10)	0.0043 (8)	0.0065 (8)	0.0070 (8)
N5	0.0473 (10)	0.0341 (10)	0.0486 (11)	−0.0012 (8)	0.0056 (8)	−0.0010 (8)
C27	0.132 (3)	0.0428 (16)	0.087 (2)	−0.0277 (18)	0.021 (2)	−0.0182 (16)
N4	0.0471 (10)	0.0395 (10)	0.0406 (10)	0.0087 (8)	0.0080 (8)	0.0085 (8)
C7	0.0463 (12)	0.0391 (12)	0.0395 (11)	0.0083 (10)	0.0026 (9)	−0.0033 (9)
C18	0.0390 (11)	0.0327 (11)	0.0421 (11)	0.0045 (9)	0.0043 (9)	0.0014 (9)
O1	0.0439 (9)	0.0694 (12)	0.0732 (13)	0.0254 (9)	−0.0082 (8)	−0.0251 (10)
O2	0.0709 (12)	0.0669 (12)	0.0464 (9)	0.0307 (10)	0.0216 (8)	0.0219 (9)
C19	0.0465 (12)	0.0367 (11)	0.0378 (11)	0.0112 (9)	0.0092 (9)	0.0038 (9)
C5	0.0432 (11)	0.0347 (11)	0.0400 (11)	0.0033 (9)	0.0012 (9)	0.0004 (9)
O3	0.0852 (13)	0.0419 (9)	0.0445 (9)	0.0005 (9)	−0.0032 (9)	0.0069 (7)
C17	0.0398 (11)	0.0352 (11)	0.0402 (11)	0.0009 (9)	0.0047 (9)	0.0012 (9)
C13	0.0487 (13)	0.0478 (14)	0.0557 (14)	0.0033 (11)	0.0073 (11)	0.0153 (11)
C31	0.0542 (14)	0.0535 (15)	0.0435 (13)	−0.0110 (12)	0.0077 (11)	−0.0074 (11)
C6	0.0438 (12)	0.0349 (11)	0.0412 (11)	0.0060 (9)	0.0044 (9)	−0.0029 (9)
C21	0.087 (2)	0.0373 (13)	0.0674 (17)	0.0171 (13)	0.0259 (16)	0.0089 (12)
C1	0.0426 (12)	0.0432 (13)	0.0523 (13)	0.0081 (10)	0.0033 (10)	−0.0012 (10)
C4	0.0551 (14)	0.0561 (15)	0.0441 (13)	0.0093 (12)	−0.0024 (11)	−0.0088 (11)
C30	0.0434 (12)	0.0454 (13)	0.0424 (12)	−0.0003 (10)	0.0028 (9)	−0.0039 (10)
C24	0.0435 (13)	0.0515 (14)	0.0597 (15)	0.0071 (11)	0.0062 (11)	0.0058 (12)
C14	0.0586 (15)	0.0644 (17)	0.0491 (14)	−0.0020 (13)	0.0124 (12)	0.0132 (12)
C25	0.0626 (15)	0.0399 (13)	0.0585 (15)	−0.0035 (11)	0.0066 (12)	0.0045 (11)
C20	0.0555 (14)	0.0422 (13)	0.0585 (15)	0.0070 (11)	0.0094 (12)	0.0036 (11)
C29	0.0498 (13)	0.0422 (13)	0.0497 (13)	−0.0042 (10)	0.0073 (11)	−0.0068 (10)
C23	0.0500 (14)	0.084 (2)	0.0590 (16)	0.0265 (14)	0.0082 (12)	0.0115 (15)
C32	0.0616 (16)	0.0540 (15)	0.0503 (14)	−0.0100 (12)	0.0015 (12)	−0.0005 (12)
C16	0.0565 (14)	0.0481 (14)	0.0521 (14)	0.0096 (11)	0.0131 (11)	0.0009 (11)
C33	0.086 (2)	0.077 (2)	0.0556 (17)	−0.0239 (18)	−0.0106 (16)	0.0101 (15)
C11	0.089 (2)	0.0368 (13)	0.0653 (17)	0.0058 (13)	0.0113 (15)	−0.0059 (12)
C12	0.0658 (16)	0.0435 (14)	0.0570 (15)	0.0007 (12)	0.0186 (12)	−0.0038 (11)
C2	0.0427 (13)	0.0603 (16)	0.0625 (16)	0.0095 (12)	−0.0041 (11)	0.0003 (13)
C22	0.085 (2)	0.0652 (19)	0.0611 (17)	0.0458 (17)	0.0277 (15)	0.0205 (14)
C8	0.0739 (18)	0.0513 (15)	0.0576 (16)	−0.0027 (13)	0.0204 (14)	−0.0051 (12)
C9	0.084 (2)	0.078 (2)	0.0618 (17)	0.0028 (17)	0.0327 (16)	−0.0137 (15)
C3	0.0541 (15)	0.0714 (18)	0.0550 (15)	0.0049 (13)	−0.0141 (12)	−0.0037 (13)
C15	0.0648 (16)	0.0647 (17)	0.0521 (15)	0.0055 (14)	0.0203 (13)	0.0008 (13)
C35	0.100 (3)	0.098 (3)	0.063 (2)	−0.018 (2)	0.0377 (19)	−0.0240 (18)
C26	0.094 (2)	0.0370 (14)	0.088 (2)	−0.0098 (14)	0.0204 (18)	0.0034 (14)
C10	0.080 (2)	0.0618 (18)	0.0586 (16)	0.0186 (15)	0.0136 (15)	−0.0186 (14)
C36	0.0677 (18)	0.082 (2)	0.0618 (17)	−0.0014 (16)	0.0121 (14)	−0.0123 (15)
C34	0.115 (3)	0.103 (3)	0.0442 (16)	−0.040 (2)	0.0093 (19)	−0.0032 (17)
C28	0.102 (2)	0.0538 (17)	0.0621 (17)	−0.0224 (16)	0.0136 (16)	−0.0154 (14)

Nd1—N2	2.604 (2)	C21—H21	0.9300
Nd1—N1	2.661 (2)	C1—C2	1.377 (3)
Nd1—N5	2.680 (2)	C1—H1	0.9300
Nd1—N4	2.6953 (19)	C4—C3	1.384 (4)
Nd1—N6	2.7018 (19)	C4—H4	0.9300
Nd1—N3	2.742 (2)	C30—C29	1.485 (3)
Nd1—Cl3	2.7686 (8)	C24—C23	1.384 (4)
Nd1—Cl2	2.7903 (9)	C24—H24	0.9300
Nd1—Cl1	2.8296 (10)	C14—C15	1.372 (4)
N2—C6	1.277 (3)	C14—H14	0.9300
N2—O1	1.380 (2)	C25—C26	1.370 (4)
N6—C30	1.275 (3)	C25—H25	0.9300
N6—O3	1.387 (2)	C20—H20	0.9300
N1—C1	1.339 (3)	C29—C28	1.380 (4)
N1—C5	1.354 (3)	C23—C22	1.371 (4)
N3—C13	1.336 (3)	C23—H23	0.9300
N3—C17	1.355 (3)	C32—C33	1.374 (4)
N5—C25	1.339 (3)	C32—H32	0.9300
N5—C29	1.342 (3)	C16—C15	1.380 (4)
C27—C26	1.363 (5)	C16—H16	0.9300
C27—C28	1.385 (4)	C33—C34	1.369 (5)
C27—H27	0.9300	C33—H33	0.9300
N4—C18	1.278 (3)	C11—C10	1.358 (4)
N4—O2	1.383 (2)	C11—C12	1.390 (4)
C7—C12	1.372 (3)	C11—H11	0.9300
C7—C8	1.386 (3)	C12—H12	0.9300
C7—C6	1.481 (3)	C2—C3	1.365 (4)
C18—C17	1.479 (3)	C2—H2	0.9300
C18—C19	1.485 (3)	C22—H22	0.9300
O1—H1A	0.8200	C8—C9	1.378 (4)
O2—H2A	0.8200	C8—H8	0.9300
C19—C24	1.377 (3)	C9—C10	1.362 (4)
C19—C20	1.390 (3)	C9—H9	0.9300
C5—C4	1.381 (3)	C3—H3	0.9300
C5—C6	1.485 (3)	C15—H15	0.9300
O3—H3A	0.8200	C35—C34	1.367 (5)
C17—C16	1.376 (3)	C35—C36	1.388 (4)
C13—C14	1.375 (4)	C35—H35	0.9300
C13—H13	0.9300	C26—H26	0.9300
C31—C32	1.389 (4)	C10—H10	0.9300
C31—C36	1.389 (4)	C36—H36	0.9300
C31—C30	1.486 (3)	C34—H34	0.9300
C21—C22	1.366 (4)	C28—H28	0.9300
C21—C20	1.379 (4)
N2—Nd1—N1	60.38 (6)	C7—C6—C5	120.62 (19)
N2—Nd1—N5	146.60 (6)	C22—C21—C20	120.3 (3)
N1—Nd1—N5	140.98 (6)	C22—C21—H21	119.9
N2—Nd1—N4	121.50 (6)	C20—C21—H21	119.9
N1—Nd1—N4	72.25 (6)	N1—C1—C2	123.5 (2)
N5—Nd1—N4	68.74 (6)	N1—C1—H1	118.3
N2—Nd1—N6	126.82 (6)	C2—C1—H1	118.3
N1—Nd1—N6	139.68 (6)	C5—C4—C3	119.1 (2)
N5—Nd1—N6	59.14 (6)	C5—C4—H4	120.4
N4—Nd1—N6	111.33 (6)	C3—C4—H4	120.4
N2—Nd1—N3	137.44 (6)	N6—C30—C29	115.7 (2)
N1—Nd1—N3	83.49 (6)	N6—C30—C31	123.3 (2)
N5—Nd1—N3	75.89 (6)	C29—C30—C31	121.0 (2)
N4—Nd1—N3	58.57 (6)	C19—C24—C23	119.5 (3)
N6—Nd1—N3	67.56 (6)	C19—C24—H24	120.3
N2—Nd1—Cl3	74.36 (5)	C23—C24—H24	120.3
N1—Nd1—Cl3	134.58 (4)	C15—C14—C13	118.6 (2)
N5—Nd1—Cl3	78.41 (5)	C15—C14—H14	120.7
N4—Nd1—Cl3	136.62 (5)	C13—C14—H14	120.7
N6—Nd1—Cl3	71.65 (5)	N5—C25—C26	123.7 (3)
N3—Nd1—Cl3	138.76 (4)	N5—C25—H25	118.1
N2—Nd1—Cl2	69.77 (5)	C26—C25—H25	118.1
N1—Nd1—Cl2	77.37 (5)	C21—C20—C19	119.4 (3)
N5—Nd1—Cl2	130.24 (4)	C21—C20—H20	120.3
N4—Nd1—Cl2	131.64 (4)	C19—C20—H20	120.3
N6—Nd1—Cl2	71.34 (5)	N5—C29—C28	121.7 (2)
N3—Nd1—Cl2	81.64 (5)	N5—C29—C30	117.4 (2)
Cl3—Nd1—Cl2	91.19 (4)	C28—C29—C30	120.9 (2)
N2—Nd1—Cl1	70.22 (5)	C22—C23—C24	120.2 (3)
N1—Nd1—Cl1	81.67 (5)	C22—C23—H23	119.9
N5—Nd1—Cl1	86.33 (5)	C24—C23—H23	119.9
N4—Nd1—Cl1	70.85 (5)	C33—C32—C31	120.5 (3)
N6—Nd1—Cl1	138.42 (5)	C33—C32—H32	119.8
N3—Nd1—Cl1	129.42 (4)	C31—C32—H32	119.8
Cl3—Nd1—Cl1	79.77 (3)	C17—C16—C15	119.1 (2)
Cl2—Nd1—Cl1	139.95 (3)	C17—C16—H16	120.5
C6—N2—O1	113.33 (18)	C15—C16—H16	120.5
C6—N2—Nd1	126.43 (14)	C34—C33—C32	119.9 (3)
O1—N2—Nd1	120.13 (13)	C34—C33—H33	120.0
C30—N6—O3	113.23 (18)	C32—C33—H33	120.0
C30—N6—Nd1	125.00 (15)	C10—C11—C12	120.1 (3)
O3—N6—Nd1	121.56 (13)	C10—C11—H11	120.0
C1—N1—C5	117.13 (19)	C12—C11—H11	120.0
C1—N1—Nd1	122.39 (15)	C7—C12—C11	120.2 (2)
C5—N1—Nd1	120.07 (14)	C7—C12—H12	119.9
C13—N3—C17	116.6 (2)	C11—C12—H12	119.9
C13—N3—Nd1	121.58 (15)	C3—C2—C1	119.0 (2)
C17—N3—Nd1	119.27 (14)	C3—C2—H2	120.5
C25—N5—C29	117.5 (2)	C1—C2—H2	120.5
C25—N5—Nd1	120.04 (16)	C21—C22—C23	120.4 (2)
C29—N5—Nd1	122.42 (15)	C21—C22—H22	119.8
C26—C27—C28	118.7 (3)	C23—C22—H22	119.8
C26—C27—H27	120.6	C9—C8—C7	120.3 (3)
C28—C27—H27	120.6	C9—C8—H8	119.8
C18—N4—O2	112.71 (17)	C7—C8—H8	119.8
C18—N4—Nd1	125.20 (14)	C10—C9—C8	120.1 (3)
O2—N4—Nd1	122.00 (12)	C10—C9—H9	120.0
C12—C7—C8	118.9 (2)	C8—C9—H9	120.0
C12—C7—C6	120.9 (2)	C2—C3—C4	119.0 (2)
C8—C7—C6	120.1 (2)	C2—C3—H3	120.5
N4—C18—C17	116.40 (18)	C4—C3—H3	120.5
N4—C18—C19	122.86 (19)	C14—C15—C16	118.9 (2)
C17—C18—C19	120.71 (18)	C14—C15—H15	120.6
N2—O1—H1A	109.5	C16—C15—H15	120.6
N4—O2—H2A	109.5	C34—C35—C36	120.1 (3)
C24—C19—C20	120.1 (2)	C34—C35—H35	120.0
C24—C19—C18	119.6 (2)	C36—C35—H35	120.0
C20—C19—C18	120.2 (2)	C27—C26—C25	118.7 (3)
N1—C5—C4	122.2 (2)	C27—C26—H26	120.6
N1—C5—C6	116.83 (19)	C25—C26—H26	120.6
C4—C5—C6	120.9 (2)	C11—C10—C9	120.5 (3)
N6—O3—H3A	109.5	C11—C10—H10	119.8
N3—C17—C16	122.7 (2)	C9—C10—H10	119.8
N3—C17—C18	116.38 (19)	C35—C36—C31	119.7 (3)
C16—C17—C18	120.9 (2)	C35—C36—H36	120.2
N3—C13—C14	124.0 (2)	C31—C36—H36	120.2
N3—C13—H13	118.0	C35—C34—C33	120.7 (3)
C14—C13—H13	118.0	C35—C34—H34	119.7
C32—C31—C36	119.1 (2)	C33—C34—H34	119.7
C32—C31—C30	120.8 (2)	C29—C28—C27	119.5 (3)
C36—C31—C30	120.1 (3)	C29—C28—H28	120.2
N2—C6—C7	124.1 (2)	C27—C28—H28	120.2
N2—C6—C5	115.26 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl3	0.82	2.22	2.966 (2)	152
O2—H2A···Cl1	0.82	2.19	2.9290 (19)	151
O3—H3A···Cl2	0.82	2.19	2.930 (2)	150

Table 1

Selected bond lengths (Å)

Nd1—N2	2.604 (2)
Nd1—N1	2.661 (2)
Nd1—N5	2.680 (2)
Nd1—N4	2.6953 (19)
Nd1—N6	2.7018 (19)
Nd1—N3	2.742 (2)
Nd1—Cl3	2.7686 (8)
Nd1—Cl2	2.7903 (9)
Nd1—Cl1	2.8296 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl3	0.82	2.22	2.966 (2)	152
O2—H2A⋯Cl1	0.82	2.19	2.9290 (19)	151
O3—H3A⋯Cl2	0.82	2.19	2.930 (2)	150