Tris[2-meth-oxy-6-(4-methyl-phenyl-iminio-meth-yl)phenolato-κO,O']tris-(thio-cyanato-κN)neodymium(III).

In the title compound, [Nd(NCS)(3)(C(15)H(15)NO(2))(3)], the Nd(III) ion is coordinated by three thio-cyanate anions [Nd-N = 2.489 (8)-2.530 (7) Å] and six O atoms [Nd-O = 2.375 (4)-2.843 (5) Å] from three zwitterionic 2-meth-oxy-6-(4-methyl-phenyl-iminiometh-yl)phenolate ligands in a tricapped trigonal-prismatic geometry. Intra-molecular N-H⋯O hydrogen bonds occur. The crystal packing exhibits weak inter-molecular C-H⋯S hydrogen bonds, π-π inter-actions with a distance of 3.904 (7) Å between the centroids of the aromatic rings, and voids of 101 Å(3).

Related literature

For related structures, see: Wang & Chang (1994 ▶); Zhao et al. (2007 ▶); Xian et al. (2008 ▶); Li et al. (2008 ▶).

Experimental

Crystal data

[Nd(NCS)3(C15H15NO2)3]

M = 1042.35

Monoclinic,

a = 16.6107 (3) Å

b = 14.2425 (3) Å

c = 22.1582 (4) Å

β = 105.972 (1)°

V = 5039.77 (17) Å3

Z = 4

Mo Kα radiation

μ = 1.21 mm−1

T = 296 K

0.14 × 0.08 × 0.05 mm

Data collection

Bruker APEXII diffractometer

44769 measured reflections

11604 independent reflections

5189 reflections with I > 2σ(I)

R int = 0.114

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.190

S = 0.86

11604 reflections

562 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.84 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053124/cv2653sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053124/cv2653Isup2.hkl

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

[Nd(NCS)3(C15H15NO2)3]	F(000) = 2124
Mr = 1042.35	Dx = 1.374 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2091 reflections
a = 16.6107 (3) Å	θ = 1.4–27.6°
b = 14.2425 (3) Å	µ = 1.21 mm−1
c = 22.1582 (4) Å	T = 296 K
β = 105.972 (1)°	Block, red
V = 5039.77 (17) Å3	0.14 × 0.08 × 0.05 mm
Z = 4

Bruker APEXII diffractometer	5189 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.114
graphite	θmax = 27.6°, θmin = 1.3°
ω scans	h = −21→21
44769 measured reflections	k = −18→18
11604 independent reflections	l = −28→28

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H-atom parameters constrained
S = 0.86	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
11604 reflections	(Δ/σ)max = 0.001
562 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.84 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
Nd	1.21267 (2)	0.27661 (3)	1.393189 (17)	0.04942 (15)
C1	1.7474 (6)	0.2005 (8)	1.6278 (6)	0.132 (4)
H1B	1.7970	0.1935	1.6140	0.197*
H1C	1.7517	0.1616	1.6639	0.197*
H1D	1.7416	0.2649	1.6386	0.197*
C2	1.6709 (6)	0.1709 (6)	1.5751 (5)	0.090 (3)
C3	1.6775 (5)	0.1410 (7)	1.5180 (6)	0.098 (3)
H3B	1.7303	0.1368	1.5115	0.118*
C4	1.6086 (5)	0.1167 (6)	1.4699 (4)	0.079 (2)
H4A	1.6150	0.0969	1.4315	0.095*
C5	1.5300 (5)	0.1220 (5)	1.4793 (4)	0.064 (2)
C6	1.5214 (5)	0.1515 (5)	1.5365 (4)	0.066 (2)
H6A	1.4686	0.1552	1.5430	0.079*
C7	1.5906 (6)	0.1754 (6)	1.5834 (4)	0.082 (2)
H7A	1.5842	0.1951	1.6218	0.099*
C8	1.4479 (5)	0.0514 (5)	1.3821 (4)	0.065 (2)
H8A	1.4939	0.0182	1.3772	0.078*
C9	1.3712 (5)	0.0448 (5)	1.3347 (4)	0.069 (2)
C10	1.3636 (7)	−0.0112 (6)	1.2797 (5)	0.097 (3)
H10A	1.4097	−0.0448	1.2752	0.116*
C11	1.2900 (8)	−0.0158 (8)	1.2340 (5)	0.110 (4)
H11A	1.2860	−0.0531	1.1988	0.132*
C12	1.2212 (7)	0.0342 (7)	1.2392 (4)	0.096 (3)
H12A	1.1713	0.0307	1.2073	0.115*
C13	1.2253 (5)	0.0892 (5)	1.2909 (4)	0.066 (2)
C14	1.3004 (5)	0.0943 (5)	1.3399 (4)	0.0613 (19)
C15	1.0798 (5)	0.1339 (7)	1.2583 (4)	0.098 (3)
H15A	1.0791	0.0822	1.2304	0.147*
H15B	1.0642	0.1904	1.2344	0.147*
H15C	1.0408	0.1221	1.2823	0.147*
C16	0.9337 (6)	0.8193 (6)	1.4168 (4)	0.092 (3)
H16A	0.9816	0.8487	1.4085	0.138*
H16B	0.9289	0.8393	1.4570	0.138*
H16C	0.8841	0.8368	1.3848	0.138*
C17	0.9441 (5)	0.7145 (5)	1.4168 (3)	0.0619 (19)
C18	0.8840 (5)	0.6555 (6)	1.4276 (4)	0.069 (2)
H18A	0.8360	0.6809	1.4348	0.083*
C19	0.8936 (4)	0.5584 (5)	1.4279 (3)	0.0601 (19)
H19A	0.8524	0.5195	1.4354	0.072*
C20	0.9633 (4)	0.5209 (5)	1.4171 (3)	0.0523 (17)
C21	1.0259 (4)	0.5778 (5)	1.4075 (3)	0.0604 (19)
H21A	1.0746	0.5520	1.4018	0.072*
C22	1.0147 (5)	0.6738 (5)	1.4067 (4)	0.071 (2)
H22A	1.0560	0.7124	1.3991	0.085*
C23	0.9246 (4)	0.3560 (5)	1.4198 (3)	0.0612 (19)
H23A	0.8711	0.3726	1.4217	0.073*
C24	0.9442 (4)	0.2599 (5)	1.4191 (3)	0.0576 (19)
C25	0.8829 (5)	0.1900 (6)	1.4185 (5)	0.089 (3)
H25A	0.8296	0.2076	1.4200	0.107*
C26	0.9016 (6)	0.0991 (7)	1.4158 (5)	0.105 (3)
H26A	0.8606	0.0539	1.4142	0.126*
C27	0.9813 (5)	0.0716 (6)	1.4151 (4)	0.083 (3)
H27A	0.9926	0.0079	1.4132	0.099*
C28	1.0438 (4)	0.1343 (5)	1.4174 (4)	0.0600 (19)
C29	1.0261 (4)	0.2302 (5)	1.4194 (3)	0.0495 (16)
C30	1.1531 (5)	0.0226 (5)	1.4252 (4)	0.086 (3)
H30A	1.1104	−0.0169	1.4333	0.129*
H30B	1.2027	0.0188	1.4598	0.129*
H30C	1.1656	0.0022	1.3875	0.129*
C31	1.6013 (7)	0.4363 (7)	1.7675 (4)	0.122 (4)
H31A	1.5565	0.4274	1.7866	0.183*
H31B	1.6238	0.4984	1.7765	0.183*
H31C	1.6446	0.3910	1.7840	0.183*
C32	1.5683 (6)	0.4236 (6)	1.6970 (4)	0.079 (2)
C33	1.4863 (6)	0.3989 (6)	1.6687 (4)	0.085 (3)
H33A	1.4496	0.3904	1.6933	0.102*
C34	1.4576 (5)	0.3865 (6)	1.6047 (4)	0.073 (2)
H34A	1.4018	0.3714	1.5862	0.088*
C35	1.5109 (4)	0.3963 (5)	1.5688 (3)	0.0514 (17)
C36	1.5935 (4)	0.4198 (5)	1.5956 (4)	0.063 (2)
H36A	1.6301	0.4266	1.5707	0.075*
C37	1.6216 (5)	0.4334 (6)	1.6600 (4)	0.075 (2)
H37A	1.6773	0.4493	1.6783	0.090*
C38	1.5238 (4)	0.3633 (4)	1.4624 (3)	0.0523 (17)
H38A	1.5819	0.3674	1.4765	0.063*
C39	1.4875 (4)	0.3426 (4)	1.3990 (3)	0.0482 (16)
C40	1.5387 (4)	0.3304 (5)	1.3584 (4)	0.064 (2)
H40A	1.5964	0.3373	1.3739	0.077*
C41	1.5055 (5)	0.3089 (6)	1.2974 (4)	0.072 (2)
H41A	1.5403	0.3005	1.2714	0.087*
C42	1.4185 (5)	0.2993 (5)	1.2729 (3)	0.0610 (19)
H42A	1.3953	0.2865	1.2305	0.073*
C43	1.3680 (4)	0.3090 (5)	1.3120 (3)	0.0522 (17)
C44	1.4000 (4)	0.3316 (5)	1.3758 (3)	0.0483 (16)
C45	1.2416 (5)	0.3000 (7)	1.2278 (4)	0.091 (3)
H45A	1.2821	0.3112	1.2050	0.137*
H45B	1.1993	0.3478	1.2178	0.137*
H45C	1.2162	0.2397	1.2166	0.137*
C46	1.2340 (4)	0.5040 (5)	1.4736 (3)	0.0591 (19)
C47	1.0439 (6)	0.3648 (7)	1.2736 (4)	0.090 (3)
C48	1.3000 (4)	0.1762 (5)	1.5462 (3)	0.0577 (18)
N1	1.4566 (4)	0.1018 (4)	1.4318 (3)	0.0628 (16)
H1A	1.4113	0.1262	1.4365	0.075*
N2	0.9766 (3)	0.4219 (4)	1.4181 (2)	0.0510 (14)
H2A	1.0258	0.4041	1.4175	0.061*
N3	1.4809 (3)	0.3773 (4)	1.5032 (3)	0.0499 (14)
H3A	1.4274	0.3748	1.4883	0.060*
N4	1.2184 (4)	0.4345 (5)	1.4465 (3)	0.0754 (18)*
N5	1.1129 (5)	0.3612 (5)	1.3056 (4)	0.094 (2)*
N6	1.2775 (4)	0.2273 (5)	1.5051 (3)	0.0677 (17)*
S1	1.25218 (13)	0.60404 (18)	1.51067 (13)	0.0996 (9)
S2	0.94976 (19)	0.3689 (2)	1.23046 (17)	0.1467 (14)
S3	1.3324 (2)	0.1029 (2)	1.60350 (12)	0.1132 (10)
O1	1.1632 (3)	0.1444 (4)	1.3004 (2)	0.0752 (15)
O2	1.3015 (3)	0.1459 (3)	1.3889 (2)	0.0561 (12)
O3	1.1243 (3)	0.1167 (3)	1.4178 (2)	0.0674 (14)
O4	1.0848 (3)	0.2913 (3)	1.4208 (2)	0.0595 (13)
O5	1.2824 (3)	0.3020 (4)	1.2938 (2)	0.0641 (13)
O6	1.3500 (2)	0.3412 (3)	1.4114 (2)	0.0538 (12)

	U11	U22	U33	U12	U13	U23
Nd	0.0425 (2)	0.0534 (3)	0.0489 (3)	0.00325 (17)	0.00670 (16)	0.0035 (2)
C1	0.084 (7)	0.122 (9)	0.152 (11)	0.005 (6)	−0.028 (7)	0.001 (8)
C2	0.073 (6)	0.069 (6)	0.104 (8)	0.013 (5)	−0.016 (6)	−0.005 (6)
C3	0.053 (5)	0.092 (7)	0.134 (10)	0.022 (5)	0.000 (6)	0.007 (7)
C4	0.066 (5)	0.084 (6)	0.088 (7)	0.018 (4)	0.019 (5)	0.007 (5)
C5	0.072 (5)	0.040 (4)	0.078 (6)	0.018 (4)	0.016 (5)	0.015 (4)
C6	0.061 (5)	0.068 (5)	0.063 (5)	0.001 (4)	0.009 (4)	0.007 (4)
C7	0.091 (6)	0.059 (5)	0.083 (7)	0.012 (5)	0.001 (5)	0.010 (5)
C8	0.074 (5)	0.048 (5)	0.073 (6)	0.015 (4)	0.023 (5)	0.001 (4)
C9	0.092 (6)	0.062 (5)	0.058 (5)	0.003 (4)	0.029 (5)	−0.010 (4)
C10	0.116 (8)	0.086 (7)	0.099 (8)	0.001 (6)	0.045 (7)	−0.031 (6)
C11	0.140 (10)	0.117 (9)	0.074 (7)	−0.021 (8)	0.031 (7)	−0.051 (6)
C12	0.118 (8)	0.094 (7)	0.073 (7)	−0.016 (6)	0.023 (6)	−0.016 (6)
C13	0.084 (6)	0.059 (5)	0.050 (5)	−0.002 (4)	0.013 (4)	−0.005 (4)
C14	0.076 (5)	0.050 (4)	0.057 (5)	0.002 (4)	0.018 (4)	0.004 (4)
C15	0.079 (6)	0.099 (7)	0.086 (7)	−0.020 (5)	−0.029 (5)	0.007 (6)
C16	0.122 (7)	0.054 (5)	0.085 (7)	0.000 (5)	0.003 (6)	0.002 (5)
C17	0.078 (5)	0.047 (5)	0.049 (5)	0.005 (4)	−0.003 (4)	−0.002 (4)
C18	0.074 (5)	0.065 (5)	0.067 (5)	0.011 (4)	0.019 (4)	−0.001 (4)
C19	0.062 (4)	0.055 (5)	0.065 (5)	−0.003 (3)	0.021 (4)	0.002 (4)
C20	0.055 (4)	0.052 (4)	0.049 (4)	−0.006 (3)	0.012 (3)	−0.001 (3)
C21	0.056 (4)	0.054 (5)	0.066 (5)	0.001 (4)	0.009 (4)	0.000 (4)
C22	0.063 (5)	0.057 (5)	0.083 (6)	−0.006 (4)	0.003 (4)	0.011 (5)
C23	0.052 (4)	0.060 (5)	0.075 (5)	−0.001 (4)	0.023 (4)	−0.006 (4)
C24	0.053 (4)	0.063 (5)	0.059 (5)	−0.004 (3)	0.018 (4)	−0.002 (4)
C25	0.076 (5)	0.072 (6)	0.136 (9)	−0.014 (5)	0.056 (6)	−0.012 (6)
C26	0.091 (7)	0.070 (7)	0.161 (10)	−0.026 (5)	0.046 (7)	−0.023 (7)
C27	0.096 (6)	0.047 (5)	0.104 (7)	−0.007 (5)	0.027 (6)	−0.002 (5)
C28	0.063 (4)	0.036 (4)	0.079 (6)	−0.004 (3)	0.017 (4)	0.003 (4)
C29	0.056 (4)	0.051 (4)	0.042 (4)	−0.012 (3)	0.013 (3)	0.003 (3)
C30	0.098 (6)	0.042 (5)	0.128 (8)	0.020 (4)	0.045 (6)	0.014 (5)
C31	0.189 (11)	0.114 (9)	0.051 (6)	−0.040 (8)	0.012 (7)	−0.017 (6)
C32	0.111 (7)	0.070 (6)	0.049 (5)	−0.015 (5)	0.013 (5)	−0.015 (4)
C33	0.112 (7)	0.090 (7)	0.064 (6)	−0.031 (5)	0.042 (6)	−0.018 (5)
C34	0.074 (5)	0.088 (6)	0.062 (6)	−0.017 (4)	0.026 (5)	−0.017 (5)
C35	0.057 (4)	0.046 (4)	0.050 (4)	−0.004 (3)	0.011 (4)	−0.007 (3)
C36	0.057 (4)	0.072 (5)	0.060 (5)	−0.013 (4)	0.018 (4)	−0.006 (4)
C37	0.075 (5)	0.077 (6)	0.063 (6)	−0.010 (4)	0.001 (5)	−0.022 (5)
C38	0.048 (4)	0.053 (4)	0.058 (5)	0.003 (3)	0.018 (4)	−0.004 (4)
C39	0.050 (4)	0.045 (4)	0.050 (4)	−0.002 (3)	0.015 (3)	0.003 (3)
C40	0.052 (4)	0.074 (5)	0.071 (6)	−0.003 (4)	0.024 (4)	−0.016 (4)
C41	0.077 (5)	0.088 (6)	0.061 (6)	−0.002 (4)	0.034 (5)	−0.011 (5)
C42	0.074 (5)	0.065 (5)	0.042 (4)	−0.003 (4)	0.013 (4)	0.005 (4)
C43	0.060 (4)	0.054 (4)	0.040 (4)	−0.007 (3)	0.009 (3)	0.002 (3)
C44	0.053 (4)	0.046 (4)	0.046 (4)	−0.002 (3)	0.013 (3)	0.006 (3)
C45	0.078 (6)	0.133 (8)	0.054 (5)	−0.017 (5)	0.001 (4)	0.025 (5)
C46	0.045 (4)	0.064 (5)	0.066 (5)	−0.010 (3)	0.012 (4)	−0.007 (4)
C47	0.079 (6)	0.102 (7)	0.080 (7)	0.013 (5)	0.007 (5)	−0.003 (5)
C48	0.068 (4)	0.064 (5)	0.043 (4)	0.012 (4)	0.018 (4)	−0.003 (4)
N1	0.062 (4)	0.050 (4)	0.074 (5)	0.010 (3)	0.016 (4)	0.003 (4)
N2	0.044 (3)	0.047 (3)	0.062 (4)	0.005 (3)	0.014 (3)	0.003 (3)
N3	0.044 (3)	0.052 (3)	0.052 (4)	0.000 (2)	0.010 (3)	−0.006 (3)
S1	0.0686 (13)	0.0964 (17)	0.145 (2)	−0.0332 (12)	0.0477 (15)	−0.0558 (17)
S2	0.094 (2)	0.142 (3)	0.161 (3)	0.0396 (18)	−0.038 (2)	−0.016 (2)
S3	0.158 (3)	0.122 (2)	0.0708 (17)	0.066 (2)	0.0515 (17)	0.0365 (16)
O1	0.073 (3)	0.082 (4)	0.059 (4)	−0.009 (3)	−0.002 (3)	0.003 (3)
O2	0.059 (3)	0.061 (3)	0.044 (3)	0.010 (2)	0.007 (2)	−0.003 (2)
O3	0.066 (3)	0.048 (3)	0.089 (4)	0.009 (2)	0.021 (3)	0.005 (3)
O4	0.051 (3)	0.046 (3)	0.084 (4)	−0.001 (2)	0.023 (3)	−0.002 (3)
O5	0.060 (3)	0.084 (4)	0.043 (3)	−0.012 (2)	0.005 (2)	0.006 (3)
O6	0.048 (2)	0.069 (3)	0.046 (3)	−0.002 (2)	0.015 (2)	−0.009 (2)

Nd—O4	2.375 (4)	C23—H23A	0.9300
Nd—O6	2.388 (4)	C24—C25	1.421 (10)
Nd—O2	2.393 (4)	C24—C29	1.423 (9)
Nd—N5	2.489 (8)	C25—C26	1.336 (12)
Nd—N6	2.517 (7)	C25—H25A	0.9300
Nd—N4	2.530 (7)	C26—C27	1.385 (12)
Nd—O1	2.742 (5)	C26—H26A	0.9300
Nd—O5	2.778 (5)	C27—C28	1.359 (10)
Nd—O3	2.843 (5)	C27—H27A	0.9300
C1—C2	1.530 (12)	C28—O3	1.357 (8)
C1—H1B	0.9600	C28—C29	1.400 (9)
C1—H1C	0.9600	C29—O4	1.302 (7)
C1—H1D	0.9600	C30—O3	1.417 (8)
C2—C3	1.366 (12)	C30—H30A	0.9600
C2—C7	1.397 (12)	C30—H30B	0.9600
C3—C4	1.376 (12)	C30—H30C	0.9600
C3—H3B	0.9300	C31—C32	1.518 (10)
C4—C5	1.380 (10)	C31—H31A	0.9600
C4—H4A	0.9300	C31—H31B	0.9600
C5—C6	1.379 (10)	C31—H31C	0.9600
C5—N1	1.405 (9)	C32—C37	1.369 (10)
C6—C7	1.363 (10)	C32—C33	1.380 (11)
C6—H6A	0.9300	C33—C34	1.379 (10)
C7—H7A	0.9300	C33—H33A	0.9300
C8—N1	1.289 (9)	C34—C35	1.350 (9)
C8—C9	1.413 (10)	C34—H34A	0.9300
C8—H8A	0.9300	C35—C36	1.379 (9)
C9—C14	1.403 (10)	C35—N3	1.427 (8)
C9—C10	1.435 (11)	C36—C37	1.388 (9)
C10—C11	1.358 (13)	C36—H36A	0.9300
C10—H10A	0.9300	C37—H37A	0.9300
C11—C12	1.380 (13)	C38—N3	1.311 (7)
C11—H11A	0.9300	C38—C39	1.400 (9)
C12—C13	1.373 (11)	C38—H38A	0.9300
C12—H12A	0.9300	C39—C40	1.409 (9)
C13—O1	1.358 (9)	C39—C44	1.410 (8)
C13—C14	1.412 (10)	C40—C41	1.347 (10)
C14—O2	1.307 (8)	C40—H40A	0.9300
C15—O1	1.450 (8)	C41—C42	1.403 (10)
C15—H15A	0.9600	C41—H41A	0.9300
C15—H15B	0.9600	C42—C43	1.369 (9)
C15—H15C	0.9600	C42—H42A	0.9300
C16—C17	1.503 (10)	C43—O5	1.371 (8)
C16—H16A	0.9600	C43—C44	1.403 (9)
C16—H16B	0.9600	C44—O6	1.301 (7)
C16—H16C	0.9600	C45—O5	1.433 (8)
C17—C18	1.374 (10)	C45—H45A	0.9600
C17—C22	1.380 (10)	C45—H45B	0.9600
C18—C19	1.391 (10)	C45—H45C	0.9600
C18—H18A	0.9300	C46—N4	1.150 (8)
C19—C20	1.355 (9)	C46—S1	1.630 (8)
C19—H19A	0.9300	C47—N5	1.171 (10)
C20—C21	1.379 (9)	C47—S2	1.594 (9)
C20—N2	1.426 (8)	C48—N6	1.145 (8)
C21—C22	1.379 (10)	C48—S3	1.617 (8)
C21—H21A	0.9300	N1—H1A	0.8600
C22—H22A	0.9300	N2—H2A	0.8600
C23—N2	1.284 (8)	N3—H3A	0.8600
C23—C24	1.408 (9)
O4—Nd—O6	143.38 (15)	C21—C22—C17	122.1 (7)
O4—Nd—O2	133.12 (15)	C21—C22—H22A	119.0
O6—Nd—O2	74.67 (15)	C17—C22—H22A	119.0
O4—Nd—N5	73.0 (2)	N2—C23—C24	123.4 (6)
O6—Nd—N5	110.2 (2)	N2—C23—H23A	118.3
O2—Nd—N5	129.1 (2)	C24—C23—H23A	118.3
O4—Nd—N6	86.67 (18)	C23—C24—C25	120.9 (7)
O6—Nd—N6	79.11 (18)	C23—C24—C29	120.9 (6)
O2—Nd—N6	73.77 (18)	C25—C24—C29	118.2 (7)
N5—Nd—N6	156.4 (2)	C26—C25—C24	120.3 (8)
O4—Nd—N4	73.90 (18)	C26—C25—H25A	119.8
O6—Nd—N4	70.59 (17)	C24—C25—H25A	119.8
O2—Nd—N4	139.96 (18)	C25—C26—C27	120.6 (8)
N5—Nd—N4	82.2 (2)	C25—C26—H26A	119.7
N6—Nd—N4	80.6 (2)	C27—C26—H26A	119.7
O4—Nd—O1	98.57 (16)	C28—C27—C26	122.4 (8)
O6—Nd—O1	117.78 (15)	C28—C27—H27A	118.8
O2—Nd—O1	59.79 (16)	C26—C27—H27A	118.8
N5—Nd—O1	75.5 (2)	O3—C28—C27	128.3 (7)
N6—Nd—O1	120.39 (18)	O3—C28—C29	113.2 (6)
N4—Nd—O1	157.76 (19)	C27—C28—C29	118.5 (7)
O4—Nd—O5	142.12 (16)	O4—C29—C28	119.4 (6)
O6—Nd—O5	59.78 (14)	O4—C29—C24	120.7 (6)
O2—Nd—O5	70.97 (15)	C28—C29—C24	119.9 (6)
N5—Nd—O5	69.7 (2)	O3—C30—H30A	109.5
N6—Nd—O5	131.17 (17)	O3—C30—H30B	109.5
N4—Nd—O5	106.50 (18)	H30A—C30—H30B	109.5
O1—Nd—O5	66.39 (15)	O3—C30—H30C	109.5
O4—Nd—O3	58.38 (13)	H30A—C30—H30C	109.5
O6—Nd—O3	142.73 (15)	H30B—C30—H30C	109.5
O2—Nd—O3	75.00 (15)	C32—C31—H31A	109.5
N5—Nd—O3	105.6 (2)	C32—C31—H31B	109.5
N6—Nd—O3	72.00 (18)	H31A—C31—H31B	109.5
N4—Nd—O3	125.27 (17)	C32—C31—H31C	109.5
O1—Nd—O3	61.95 (15)	H31A—C31—H31C	109.5
O5—Nd—O3	127.32 (14)	H31B—C31—H31C	109.5
C2—C1—H1B	109.5	C37—C32—C33	118.4 (8)
C2—C1—H1C	109.5	C37—C32—C31	119.6 (8)
H1B—C1—H1C	109.5	C33—C32—C31	122.0 (9)
C2—C1—H1D	109.5	C34—C33—C32	121.2 (8)
H1B—C1—H1D	109.5	C34—C33—H33A	119.4
H1C—C1—H1D	109.5	C32—C33—H33A	119.4
C3—C2—C7	117.3 (9)	C35—C34—C33	119.8 (8)
C3—C2—C1	122.1 (10)	C35—C34—H34A	120.1
C7—C2—C1	120.7 (11)	C33—C34—H34A	120.1
C2—C3—C4	122.3 (9)	C34—C35—C36	120.6 (7)
C2—C3—H3B	118.8	C34—C35—N3	118.6 (6)
C4—C3—H3B	118.8	C36—C35—N3	120.8 (6)
C3—C4—C5	119.2 (9)	C35—C36—C37	119.3 (7)
C3—C4—H4A	120.4	C35—C36—H36A	120.3
C5—C4—H4A	120.4	C37—C36—H36A	120.3
C6—C5—C4	119.8 (8)	C32—C37—C36	120.8 (7)
C6—C5—N1	117.6 (7)	C32—C37—H37A	119.6
C4—C5—N1	122.5 (8)	C36—C37—H37A	119.6
C7—C6—C5	119.8 (8)	N3—C38—C39	123.9 (6)
C7—C6—H6A	120.1	N3—C38—H38A	118.0
C5—C6—H6A	120.1	C39—C38—H38A	118.0
C6—C7—C2	121.6 (9)	C38—C39—C40	119.9 (6)
C6—C7—H7A	119.2	C38—C39—C44	120.4 (6)
C2—C7—H7A	119.2	C40—C39—C44	119.7 (6)
N1—C8—C9	122.6 (7)	C41—C40—C39	121.1 (7)
N1—C8—H8A	118.7	C41—C40—H40A	119.5
C9—C8—H8A	118.7	C39—C40—H40A	119.5
C14—C9—C8	120.7 (7)	C40—C41—C42	120.3 (7)
C14—C9—C10	118.0 (8)	C40—C41—H41A	119.9
C8—C9—C10	121.3 (8)	C42—C41—H41A	119.9
C11—C10—C9	120.7 (9)	C43—C42—C41	119.4 (7)
C11—C10—H10A	119.6	C43—C42—H42A	120.3
C9—C10—H10A	119.6	C41—C42—H42A	120.3
C10—C11—C12	120.7 (9)	C42—C43—O5	125.0 (6)
C10—C11—H11A	119.7	C42—C43—C44	122.2 (6)
C12—C11—H11A	119.7	O5—C43—C44	112.8 (6)
C13—C12—C11	120.8 (10)	O6—C44—C43	120.4 (6)
C13—C12—H12A	119.6	O6—C44—C39	122.2 (6)
C11—C12—H12A	119.6	C43—C44—C39	117.4 (6)
O1—C13—C12	126.4 (8)	O5—C45—H45A	109.5
O1—C13—C14	113.4 (7)	O5—C45—H45B	109.5
C12—C13—C14	120.1 (8)	H45A—C45—H45B	109.5
O2—C14—C9	122.0 (7)	O5—C45—H45C	109.5
O2—C14—C13	118.4 (7)	H45A—C45—H45C	109.5
C9—C14—C13	119.6 (7)	H45B—C45—H45C	109.5
O1—C15—H15A	109.5	N4—C46—S1	177.7 (7)
O1—C15—H15B	109.5	N5—C47—S2	179.4 (11)
H15A—C15—H15B	109.5	N6—C48—S3	179.1 (7)
O1—C15—H15C	109.5	C8—N1—C5	128.6 (7)
H15A—C15—H15C	109.5	C8—N1—H1A	115.7
H15B—C15—H15C	109.5	C5—N1—H1A	115.7
C17—C16—H16A	109.5	C23—N2—C20	128.4 (6)
C17—C16—H16B	109.5	C23—N2—H2A	115.8
H16A—C16—H16B	109.5	C20—N2—H2A	115.8
C17—C16—H16C	109.5	C38—N3—C35	128.9 (6)
H16A—C16—H16C	109.5	C38—N3—H3A	115.6
H16B—C16—H16C	109.5	C35—N3—H3A	115.6
C18—C17—C22	117.5 (7)	C46—N4—Nd	169.5 (6)
C18—C17—C16	121.3 (7)	C47—N5—Nd	145.5 (7)
C22—C17—C16	121.3 (7)	C48—N6—Nd	156.7 (6)
C17—C18—C19	121.4 (7)	C13—O1—C15	118.2 (7)
C17—C18—H18A	119.3	C13—O1—Nd	115.5 (4)
C19—C18—H18A	119.3	C15—O1—Nd	126.1 (5)
C20—C19—C18	119.5 (7)	C14—O2—Nd	127.0 (4)
C20—C19—H19A	120.2	C28—O3—C30	118.4 (6)
C18—C19—H19A	120.2	C28—O3—Nd	114.2 (4)
C19—C20—C21	120.8 (7)	C30—O3—Nd	127.1 (4)
C19—C20—N2	121.5 (6)	C29—O4—Nd	130.7 (4)
C21—C20—N2	117.6 (6)	C43—O5—C45	117.5 (6)
C20—C21—C22	118.7 (7)	C43—O5—Nd	113.7 (4)
C20—C21—H21A	120.6	C45—O5—Nd	128.6 (4)
C22—C21—H21A	120.6	C44—O6—Nd	126.7 (4)
C7—C2—C3—C4	0.6 (14)	O5—Nd—N5—C47	131.5 (13)
C1—C2—C3—C4	−178.2 (9)	O3—Nd—N5—C47	6.9 (13)
C2—C3—C4—C5	−0.5 (14)	O4—Nd—N6—C48	93.5 (14)
C3—C4—C5—C6	0.1 (12)	O6—Nd—N6—C48	−120.4 (14)
C3—C4—C5—N1	177.5 (7)	O2—Nd—N6—C48	−43.4 (14)
C4—C5—C6—C7	0.0 (11)	N5—Nd—N6—C48	123.6 (14)
N1—C5—C6—C7	−177.5 (7)	N4—Nd—N6—C48	167.7 (14)
C5—C6—C7—C2	0.2 (12)	O1—Nd—N6—C48	−4.5 (15)
C3—C2—C7—C6	−0.5 (13)	O5—Nd—N6—C48	−88.5 (14)
C1—C2—C7—C6	178.4 (8)	O3—Nd—N6—C48	35.7 (14)
N1—C8—C9—C14	0.5 (12)	C12—C13—O1—C15	11.3 (12)
N1—C8—C9—C10	179.5 (8)	C14—C13—O1—C15	−170.5 (7)
C14—C9—C10—C11	0.1 (13)	C12—C13—O1—Nd	−163.8 (7)
C8—C9—C10—C11	−178.9 (9)	C14—C13—O1—Nd	14.4 (8)
C9—C10—C11—C12	0.8 (16)	O4—Nd—O1—C13	−153.4 (5)
C10—C11—C12—C13	−0.5 (16)	O6—Nd—O1—C13	31.3 (5)
C11—C12—C13—O1	177.3 (9)	O2—Nd—O1—C13	−18.0 (4)
C11—C12—C13—C14	−0.8 (13)	N5—Nd—O1—C13	136.8 (5)
C8—C9—C14—O2	−2.0 (11)	N6—Nd—O1—C13	−62.2 (5)
C10—C9—C14—O2	179.0 (7)	N4—Nd—O1—C13	138.5 (6)
C8—C9—C14—C13	177.7 (7)	O5—Nd—O1—C13	63.0 (5)
C10—C9—C14—C13	−1.3 (11)	O3—Nd—O1—C13	−106.3 (5)
O1—C13—C14—O2	3.0 (10)	O4—Nd—O1—C15	32.0 (6)
C12—C13—C14—O2	−178.7 (7)	O6—Nd—O1—C15	−143.3 (6)
O1—C13—C14—C9	−176.6 (7)	O2—Nd—O1—C15	167.4 (6)
C12—C13—C14—C9	1.7 (11)	N5—Nd—O1—C15	−37.8 (6)
C22—C17—C18—C19	−0.4 (12)	N6—Nd—O1—C15	123.2 (6)
C16—C17—C18—C19	−179.8 (7)	N4—Nd—O1—C15	−36.1 (8)
C17—C18—C19—C20	−0.3 (12)	O5—Nd—O1—C15	−111.6 (6)
C18—C19—C20—C21	1.8 (11)	O3—Nd—O1—C15	79.1 (6)
C18—C19—C20—N2	178.8 (6)	C9—C14—O2—Nd	155.3 (5)
C19—C20—C21—C22	−2.5 (11)	C13—C14—O2—Nd	−24.4 (9)
N2—C20—C21—C22	−179.6 (6)	O4—Nd—O2—C14	94.2 (6)
C20—C21—C22—C17	1.8 (12)	O6—Nd—O2—C14	−113.8 (5)
C18—C17—C22—C21	−0.4 (12)	N5—Nd—O2—C14	−10.0 (6)
C16—C17—C22—C21	179.0 (7)	N6—Nd—O2—C14	163.3 (6)
N2—C23—C24—C25	−177.4 (8)	N4—Nd—O2—C14	−144.3 (5)
N2—C23—C24—C29	3.1 (12)	O1—Nd—O2—C14	22.2 (5)
C23—C24—C25—C26	177.8 (9)	O5—Nd—O2—C14	−51.0 (5)
C29—C24—C25—C26	−2.7 (14)	O3—Nd—O2—C14	88.1 (5)
C24—C25—C26—C27	1.8 (16)	C27—C28—O3—C30	−9.3 (12)
C25—C26—C27—C28	0.1 (16)	C29—C28—O3—C30	170.8 (7)
C26—C27—C28—O3	179.2 (9)	C27—C28—O3—Nd	165.9 (7)
C26—C27—C28—C29	−0.9 (14)	C29—C28—O3—Nd	−14.0 (8)
O3—C28—C29—O4	0.8 (10)	O4—Nd—O3—C28	15.7 (5)
C27—C28—C29—O4	−179.1 (7)	O6—Nd—O3—C28	154.0 (4)
O3—C28—C29—C24	179.9 (6)	O2—Nd—O3—C28	−169.5 (5)
C27—C28—C29—C24	0.0 (11)	N5—Nd—O3—C28	−42.4 (5)
C23—C24—C29—O4	0.4 (11)	N6—Nd—O3—C28	113.0 (5)
C25—C24—C29—O4	−179.1 (7)	N4—Nd—O3—C28	49.1 (5)
C23—C24—C29—C28	−178.7 (7)	O1—Nd—O3—C28	−106.1 (5)
C25—C24—C29—C28	1.8 (11)	O5—Nd—O3—C28	−118.4 (5)
C37—C32—C33—C34	−1.6 (14)	O4—Nd—O3—C30	−169.6 (7)
C31—C32—C33—C34	−179.1 (9)	O6—Nd—O3—C30	−31.3 (7)
C32—C33—C34—C35	1.7 (13)	O2—Nd—O3—C30	5.2 (6)
C33—C34—C35—C36	−0.9 (12)	N5—Nd—O3—C30	132.3 (6)
C33—C34—C35—N3	176.1 (7)	N6—Nd—O3—C30	−72.3 (6)
C34—C35—C36—C37	0.0 (11)	N4—Nd—O3—C30	−136.2 (6)
N3—C35—C36—C37	−176.9 (7)	O1—Nd—O3—C30	68.6 (6)
C33—C32—C37—C36	0.8 (13)	O5—Nd—O3—C30	56.2 (6)
C31—C32—C37—C36	178.4 (8)	C28—C29—O4—Nd	18.9 (9)
C35—C36—C37—C32	0.0 (12)	C24—C29—O4—Nd	−160.2 (5)
N3—C38—C39—C40	178.8 (6)	O6—Nd—O4—C29	−155.9 (5)
N3—C38—C39—C44	−2.8 (10)	O2—Nd—O4—C29	−25.1 (7)
C38—C39—C40—C41	178.9 (7)	N5—Nd—O4—C29	103.0 (6)
C44—C39—C40—C41	0.5 (11)	N6—Nd—O4—C29	−89.1 (6)
C39—C40—C41—C42	0.7 (12)	N4—Nd—O4—C29	−170.3 (6)
C40—C41—C42—C43	−2.1 (12)	O1—Nd—O4—C29	31.1 (6)
C41—C42—C43—O5	179.5 (7)	O5—Nd—O4—C29	93.3 (6)
C41—C42—C43—C44	2.2 (11)	O3—Nd—O4—C29	−18.3 (5)
C42—C43—C44—O6	179.3 (6)	C42—C43—O5—C45	−11.0 (10)
O5—C43—C44—O6	1.7 (9)	C44—C43—O5—C45	166.5 (6)
C42—C43—C44—C39	−1.0 (10)	C42—C43—O5—Nd	163.6 (6)
O5—C43—C44—C39	−178.6 (6)	C44—C43—O5—Nd	−18.9 (7)
C38—C39—C44—O6	0.9 (10)	O4—Nd—O5—C43	160.4 (4)
C40—C39—C44—O6	179.4 (6)	O6—Nd—O5—C43	20.6 (4)
C38—C39—C44—C43	−178.8 (6)	O2—Nd—O5—C43	−62.4 (4)
C40—C39—C44—C43	−0.3 (10)	N5—Nd—O5—C43	150.5 (5)
C9—C8—N1—C5	−173.3 (7)	N6—Nd—O5—C43	−16.3 (5)
C6—C5—N1—C8	−160.0 (7)	N4—Nd—O5—C43	75.6 (5)
C4—C5—N1—C8	22.5 (11)	O1—Nd—O5—C43	−126.9 (5)
C24—C23—N2—C20	178.3 (7)	O3—Nd—O5—C43	−115.0 (4)
C19—C20—N2—C23	10.6 (11)	O4—Nd—O5—C45	−25.8 (7)
C21—C20—N2—C23	−172.3 (7)	O6—Nd—O5—C45	−165.6 (7)
C39—C38—N3—C35	178.2 (6)	O2—Nd—O5—C45	111.5 (6)
C34—C35—N3—C38	−164.5 (7)	N5—Nd—O5—C45	−35.7 (6)
C36—C35—N3—C38	12.5 (10)	N6—Nd—O5—C45	157.5 (6)
O4—Nd—N4—C46	150 (3)	N4—Nd—O5—C45	−110.6 (6)
O6—Nd—N4—C46	−21 (3)	O1—Nd—O5—C45	46.9 (6)
O2—Nd—N4—C46	10 (4)	O3—Nd—O5—C45	58.8 (7)
N5—Nd—N4—C46	−136 (3)	C43—C44—O6—Nd	22.3 (9)
N6—Nd—N4—C46	61 (3)	C39—C44—O6—Nd	−157.3 (5)
O1—Nd—N4—C46	−137 (3)	O4—Nd—O6—C44	−160.7 (5)
O5—Nd—N4—C46	−70 (3)	O2—Nd—O6—C44	54.3 (5)
O3—Nd—N4—C46	121 (3)	N5—Nd—O6—C44	−72.3 (5)
O4—Nd—N5—C47	−42.1 (12)	N6—Nd—O6—C44	130.2 (5)
O6—Nd—N5—C47	176.5 (12)	N4—Nd—O6—C44	−146.0 (5)
O2—Nd—N5—C47	90.1 (13)	O1—Nd—O6—C44	11.5 (5)
N6—Nd—N5—C47	−73.7 (15)	O5—Nd—O6—C44	−22.3 (5)
N4—Nd—N5—C47	−117.6 (13)	O3—Nd—O6—C44	90.8 (5)
O1—Nd—N5—C47	61.8 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	1.86	2.566 (7)	138
N2—H2A···O4	0.86	1.87	2.576 (6)	138
N3—H3A···O6	0.86	1.89	2.589 (7)	137
C38—H38A···S1i	0.93	2.72	3.633 (6)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.86	1.86	2.566 (7)	138
N2—H2A⋯O4	0.86	1.87	2.576 (6)	138
N3—H3A⋯O6	0.86	1.89	2.589 (7)	137
C38—H38A⋯S1i	0.93	2.72	3.633 (6)	166

Symmetry code: (i) .