Tetra-kis(nitrato-κ(2)O,O')[N,N'-1,4-phenyl-enebis(pyridine-4-carboxamide)-κN(1)](4-{[4-(pyridine-4-carboxamido-κN(1))phen-yl]carbamo-yl}pyridin-1-ium)neodymium(III).

In the title compound, [Nd(NO(3))(4)(C(18)H(15)N(4)O(2))(C(18)H(14)N(4)O(2))], the Nd(III) centre is located on a twofold axis and exhibits a ten-coordinated distorted bicapped square-anti-prismatic geometry. The pyridinium NH H atom is disordered over the two ligands. Adjacent mononuclear clusters are linked through N-H⋯O and N-H⋯N hydrogen-bonding inter-actions, generating layers in the (102) plane.

Related literature

For general background to octa­cyano­metallate-based compounds, see: Sieklucka et al. (2011 ▶); Zhou et al. (2010 ▶); Bok et al. (1975 ▶). For background to N,N′-bis­(4-pyridyl­formamide)-1,4-benzene, see: Niu et al. (2004 ▶); Pansanel et al. (2006 ▶); Song et al. (2009 ▶).

Experimental

Crystal data

[Nd(NO3)4(C18H15N4O2)(C18H14N4O2)]

M = 1029.95

Monoclinic,

a = 19.856 (4) Å

b = 7.8491 (14) Å

c = 25.338 (5) Å

β = 95.153 (2)°

V = 3933.0 (13) Å3

Z = 4

Mo Kα radiation

μ = 1.41 mm−1

T = 291 K

0.28 × 0.24 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.693, T max = 0.746

14547 measured reflections

3853 independent reflections

3510 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.070

S = 0.99

3853 reflections

294 parameters

H-atom parameters constrained

Δρmax = 1.29 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812011397/bt5847sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011397/bt5847Isup2.hkl

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

[Nd(NO3)4(C18H15N4O2)(C18H14N4O2)]	F(000) = 2068
Mr = 1029.95	Dx = 1.739 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5566 reflections
a = 19.856 (4) Å	θ = 2.5–25.6°
b = 7.8491 (14) Å	µ = 1.41 mm−1
c = 25.338 (5) Å	T = 291 K
β = 95.153 (2)°	Block, yellow
V = 3933.0 (13) Å3	0.28 × 0.24 × 0.22 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3853 independent reflections
Radiation source: fine-focus sealed tube	3510 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −24→24
Tmin = 0.693, Tmax = 0.746	k = −8→9
14547 measured reflections	l = −31→31

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0368P)2 + 4.9413P] where P = (Fo2 + 2Fc2)/3
3853 reflections	(Δ/σ)max < 0.001
294 parameters	Δρmax = 1.29 e Å−3
0 restraints	Δρmin = −0.36 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	Occ. (<1)
Nd1	0.0000	0.03144 (3)	0.2500	0.02816 (8)
O1	0.12544 (12)	−0.0024 (3)	0.23734 (10)	0.0500 (6)
N1	0.05042 (13)	0.2942 (3)	0.19938 (10)	0.0375 (6)
C1	0.08058 (16)	0.4270 (4)	0.22500 (13)	0.0410 (7)
H1	0.0736	0.4421	0.2605	0.049*
O2	0.10174 (13)	0.1272 (3)	0.30864 (9)	0.0541 (6)
N2	0.14665 (14)	0.0697 (4)	0.28005 (13)	0.0522 (8)
C2	0.12163 (16)	0.5434 (4)	0.20184 (12)	0.0391 (7)
H2	0.1411	0.6339	0.2214	0.047*
O3	0.20657 (14)	0.0853 (5)	0.29318 (15)	0.0981 (12)
N3	−0.02515 (13)	−0.2346 (3)	0.16730 (10)	0.0386 (6)
C3	0.13313 (14)	0.5224 (4)	0.14925 (12)	0.0345 (6)
O4	−0.05520 (12)	−0.2346 (3)	0.20850 (9)	0.0493 (6)
N4	0.18418 (12)	0.7980 (3)	0.13715 (10)	0.0390 (6)
H4A	0.1615	0.8285	0.1644	0.047*
C4	0.10281 (17)	0.3846 (4)	0.12217 (12)	0.0412 (7)
H4	0.1097	0.3652	0.0868	0.049*
O5	0.01619 (12)	−0.1125 (3)	0.16218 (9)	0.0497 (6)
N5	0.32465 (13)	1.3637 (3)	0.06645 (11)	0.0425 (6)
H5A	0.3067	1.4584	0.0785	0.051*
C5	0.06243 (16)	0.2773 (4)	0.14848 (12)	0.0413 (7)
H5	0.0420	0.1866	0.1296	0.050*
O6	−0.03444 (14)	−0.3447 (4)	0.13396 (10)	0.0657 (7)
N6	0.45861 (13)	1.8629 (3)	0.00603 (11)	0.0449 (7)
H6	0.4815	1.9600	0.0045	0.054*	0.50
C6	0.17860 (15)	0.6371 (4)	0.11988 (12)	0.0358 (7)
O7	0.20613 (13)	0.5820 (3)	0.08216 (10)	0.0566 (6)
C7	0.22349 (15)	0.9311 (4)	0.11767 (13)	0.0366 (7)
O8	0.38974 (12)	1.2586 (3)	0.00483 (10)	0.0542 (6)
C8	0.23701 (19)	1.0708 (4)	0.15034 (14)	0.0516 (9)
H8	0.2231	1.0708	0.1844	0.062*
C9	0.27096 (19)	1.2096 (5)	0.13266 (14)	0.0525 (9)
H9	0.2790	1.3035	0.1547	0.063*
C10	0.29314 (15)	1.2111 (4)	0.08252 (12)	0.0384 (7)
C11	0.28130 (16)	1.0710 (4)	0.05014 (13)	0.0404 (7)
H11	0.2966	1.0703	0.0165	0.048*
C12	0.24663 (16)	0.9308 (4)	0.06760 (13)	0.0401 (7)
H12	0.2389	0.8366	0.0456	0.048*
C13	0.36928 (15)	1.3780 (4)	0.02994 (12)	0.0376 (7)
C14	0.39656 (15)	1.5559 (4)	0.02252 (12)	0.0363 (7)
C15	0.39694 (17)	1.6835 (4)	0.05940 (13)	0.0445 (8)
H15	0.3761	1.6679	0.0905	0.053*
C16	0.42859 (18)	1.8357 (4)	0.04990 (14)	0.0490 (8)
H16	0.4288	1.9219	0.0751	0.059*
C17	0.45621 (16)	1.7421 (5)	−0.03105 (13)	0.0470 (8)
H17	0.4757	1.7630	−0.0624	0.056*
C18	0.42595 (16)	1.5886 (4)	−0.02424 (13)	0.0432 (7)
H18	0.4250	1.5063	−0.0507	0.052*

	U11	U22	U33	U12	U13	U23
Nd1	0.03137 (12)	0.02393 (12)	0.03054 (12)	0.000	0.01028 (8)	0.000
O1	0.0389 (12)	0.0579 (16)	0.0550 (15)	0.0037 (10)	0.0140 (11)	0.0070 (11)
N1	0.0421 (14)	0.0277 (14)	0.0441 (15)	−0.0043 (11)	0.0117 (11)	0.0039 (11)
C1	0.0498 (18)	0.0317 (18)	0.0434 (17)	−0.0036 (14)	0.0149 (14)	0.0018 (13)
O2	0.0614 (16)	0.0571 (16)	0.0424 (13)	−0.0094 (12)	−0.0036 (11)	−0.0003 (11)
N2	0.0366 (15)	0.058 (2)	0.061 (2)	−0.0048 (13)	−0.0022 (14)	0.0215 (15)
C2	0.0446 (17)	0.0303 (16)	0.0434 (17)	−0.0051 (13)	0.0097 (13)	−0.0034 (13)
O3	0.0409 (16)	0.122 (3)	0.126 (3)	−0.0114 (17)	−0.0256 (17)	0.027 (2)
N3	0.0445 (15)	0.0312 (14)	0.0406 (14)	−0.0007 (11)	0.0067 (11)	−0.0052 (11)
C3	0.0329 (14)	0.0270 (15)	0.0445 (17)	0.0001 (12)	0.0085 (12)	0.0048 (12)
O4	0.0651 (15)	0.0403 (13)	0.0457 (13)	−0.0136 (11)	0.0228 (11)	−0.0057 (10)
N4	0.0403 (14)	0.0321 (15)	0.0472 (15)	−0.0051 (11)	0.0187 (11)	0.0033 (11)
C4	0.0526 (19)	0.0349 (18)	0.0373 (16)	−0.0075 (15)	0.0105 (14)	0.0009 (13)
O5	0.0597 (14)	0.0437 (14)	0.0494 (13)	−0.0146 (12)	0.0247 (11)	−0.0082 (11)
N5	0.0478 (15)	0.0272 (14)	0.0557 (16)	−0.0075 (11)	0.0226 (13)	−0.0010 (11)
C5	0.0478 (18)	0.0334 (17)	0.0430 (18)	−0.0086 (14)	0.0050 (14)	0.0015 (13)
O6	0.0768 (18)	0.0620 (18)	0.0598 (16)	−0.0183 (14)	0.0153 (13)	−0.0294 (13)
N6	0.0406 (15)	0.0378 (16)	0.0565 (17)	−0.0121 (12)	0.0053 (12)	0.0087 (13)
C6	0.0349 (15)	0.0312 (17)	0.0424 (17)	−0.0015 (12)	0.0102 (13)	0.0020 (12)
O7	0.0724 (17)	0.0382 (13)	0.0647 (16)	−0.0087 (12)	0.0373 (13)	−0.0040 (11)
C7	0.0339 (15)	0.0279 (17)	0.0495 (18)	−0.0045 (12)	0.0117 (13)	0.0043 (12)
O8	0.0538 (14)	0.0405 (14)	0.0723 (16)	−0.0109 (11)	0.0276 (12)	−0.0106 (12)
C8	0.067 (2)	0.043 (2)	0.049 (2)	−0.0161 (17)	0.0284 (17)	−0.0039 (15)
C9	0.066 (2)	0.042 (2)	0.053 (2)	−0.0170 (17)	0.0239 (17)	−0.0108 (16)
C10	0.0352 (15)	0.0317 (17)	0.0498 (18)	−0.0056 (13)	0.0123 (13)	0.0026 (13)
C11	0.0438 (17)	0.0389 (19)	0.0396 (17)	−0.0097 (14)	0.0100 (13)	0.0025 (13)
C12	0.0432 (17)	0.0326 (18)	0.0451 (18)	−0.0092 (13)	0.0081 (14)	−0.0016 (13)
C13	0.0333 (15)	0.0381 (19)	0.0422 (17)	−0.0051 (13)	0.0074 (13)	−0.0019 (14)
C14	0.0320 (15)	0.0371 (18)	0.0405 (16)	−0.0055 (12)	0.0074 (12)	0.0030 (13)
C15	0.0502 (19)	0.043 (2)	0.0416 (17)	−0.0131 (15)	0.0125 (14)	−0.0019 (14)
C16	0.053 (2)	0.0404 (19)	0.054 (2)	−0.0121 (16)	0.0068 (16)	−0.0053 (15)
C17	0.0449 (18)	0.050 (2)	0.0473 (19)	−0.0064 (16)	0.0122 (15)	0.0096 (16)
C18	0.0439 (18)	0.0451 (19)	0.0422 (17)	−0.0077 (15)	0.0122 (14)	−0.0024 (14)

Nd1—O2	2.513 (2)	C4—H4	0.9300
Nd1—O2i	2.513 (2)	N5—C13	1.342 (4)
Nd1—O5	2.542 (2)	N5—C10	1.428 (4)
Nd1—O5i	2.542 (2)	N5—H5A	0.8900
Nd1—O4	2.542 (2)	C5—H5	0.9300
Nd1—O4i	2.542 (2)	N6—C16	1.325 (4)
Nd1—O1i	2.554 (2)	N6—C17	1.333 (4)
Nd1—O1	2.554 (2)	N6—H6	0.8900
Nd1—N1	2.671 (2)	C6—O7	1.222 (4)
Nd1—N1i	2.671 (2)	C7—C8	1.385 (5)
Nd1—N2i	2.958 (3)	C7—C12	1.388 (4)
Nd1—N2	2.958 (3)	O8—C13	1.222 (4)
O1—N2	1.260 (4)	C8—C9	1.377 (5)
N1—C1	1.340 (4)	C8—H8	0.9300
N1—C5	1.339 (4)	C9—C10	1.382 (4)
C1—C2	1.389 (4)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.380 (4)
O2—N2	1.281 (4)	C11—C12	1.391 (4)
N2—O3	1.213 (4)	C11—H11	0.9300
C2—C3	1.382 (4)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.516 (4)
N3—O6	1.211 (3)	C14—C15	1.369 (4)
N3—O4	1.248 (3)	C14—C18	1.391 (4)
N3—O5	1.276 (3)	C15—C16	1.381 (5)
C3—C4	1.389 (4)	C15—H15	0.9300
C3—C6	1.517 (4)	C16—H16	0.9300
N4—C6	1.338 (4)	C17—C18	1.364 (5)
N4—C7	1.419 (4)	C17—H17	0.9300
N4—H4A	0.8902	C18—H18	0.9300
C4—C5	1.376 (4)
O2—Nd1—O2i	145.18 (12)	O3—N2—O1	121.7 (4)
O2—Nd1—O5	119.51 (8)	O3—N2—O2	121.7 (4)
O2i—Nd1—O5	76.91 (8)	O1—N2—O2	116.6 (3)
O2—Nd1—O5i	76.91 (8)	O3—N2—Nd1	179.0 (3)
O2i—Nd1—O5i	119.51 (8)	O1—N2—Nd1	59.20 (15)
O5—Nd1—O5i	127.20 (11)	O2—N2—Nd1	57.46 (15)
O2—Nd1—O4	141.65 (8)	C3—C2—C1	118.9 (3)
O2i—Nd1—O4	72.99 (8)	C3—C2—H2	120.6
O5—Nd1—O4	49.93 (7)	C1—C2—H2	120.6
O5i—Nd1—O4	85.01 (8)	O6—N3—O4	121.9 (3)
O2—Nd1—O4i	72.99 (8)	O6—N3—O5	121.6 (3)
O2i—Nd1—O4i	141.65 (8)	O4—N3—O5	116.5 (2)
O5—Nd1—O4i	85.01 (8)	O6—N3—Nd1	178.8 (2)
O5i—Nd1—O4i	49.93 (7)	O4—N3—Nd1	58.16 (14)
O4—Nd1—O4i	69.51 (11)	O5—N3—Nd1	58.30 (14)
O2—Nd1—O1i	134.28 (8)	C2—C3—C4	117.9 (3)
O2i—Nd1—O1i	50.51 (8)	C2—C3—C6	124.0 (3)
O5—Nd1—O1i	105.38 (8)	C4—C3—C6	118.1 (3)
O5i—Nd1—O1i	69.04 (8)	N3—O4—Nd1	97.18 (16)
O4—Nd1—O1i	65.00 (8)	C6—N4—C7	127.8 (3)
O4i—Nd1—O1i	104.58 (8)	C6—N4—H4A	118.3
O2—Nd1—O1	50.51 (8)	C7—N4—H4A	113.8
O2i—Nd1—O1	134.28 (8)	C5—C4—C3	118.9 (3)
O5—Nd1—O1	69.04 (8)	C5—C4—H4	120.6
O5i—Nd1—O1	105.38 (8)	C3—C4—H4	120.6
O4—Nd1—O1	104.58 (8)	N3—O5—Nd1	96.42 (16)
O4i—Nd1—O1	65.00 (8)	C13—N5—C10	126.9 (3)
O1i—Nd1—O1	168.06 (11)	C13—N5—H5A	118.5
O2—Nd1—N1	74.74 (8)	C10—N5—H5A	113.8
O2i—Nd1—N1	78.52 (8)	N1—C5—C4	124.6 (3)
O5—Nd1—N1	80.83 (8)	N1—C5—H5	117.7
O5i—Nd1—N1	147.80 (8)	C4—C5—H5	117.7
O4—Nd1—N1	127.02 (7)	C16—N6—C17	119.1 (3)
O4i—Nd1—N1	131.83 (8)	C16—N6—H6	116.3
O1i—Nd1—N1	123.55 (8)	C17—N6—H6	124.4
O1—Nd1—N1	66.92 (8)	O7—C6—N4	124.1 (3)
O2—Nd1—N1i	78.52 (8)	O7—C6—C3	120.1 (3)
O2i—Nd1—N1i	74.74 (8)	N4—C6—C3	115.8 (3)
O5—Nd1—N1i	147.80 (8)	C8—C7—C12	119.0 (3)
O5i—Nd1—N1i	80.83 (8)	C8—C7—N4	117.3 (3)
O4—Nd1—N1i	131.83 (8)	C12—C7—N4	123.7 (3)
O4i—Nd1—N1i	127.02 (7)	C9—C8—C7	120.4 (3)
O1i—Nd1—N1i	66.92 (8)	C9—C8—H8	119.8
O1—Nd1—N1i	123.55 (8)	C7—C8—H8	119.8
N1—Nd1—N1i	78.88 (11)	C10—C9—C8	120.8 (3)
O2—Nd1—N2i	147.38 (8)	C10—C9—H9	119.6
O2i—Nd1—N2i	25.44 (8)	C8—C9—H9	119.6
O5—Nd1—N2i	91.07 (8)	C9—C10—C11	119.3 (3)
O5i—Nd1—N2i	94.10 (9)	C9—C10—N5	117.0 (3)
O4—Nd1—N2i	66.36 (8)	C11—C10—N5	123.7 (3)
O4i—Nd1—N2i	124.59 (9)	C10—C11—C12	120.3 (3)
O1i—Nd1—N2i	25.07 (9)	C10—C11—H11	119.9
O1—Nd1—N2i	157.96 (8)	C12—C11—H11	119.9
N1—Nd1—N2i	101.58 (9)	C7—C12—C11	120.2 (3)
N1i—Nd1—N2i	69.05 (8)	C7—C12—H12	119.9
O2—Nd1—N2	25.44 (8)	C11—C12—H12	119.9
O2i—Nd1—N2	147.38 (8)	O8—C13—N5	124.5 (3)
O5—Nd1—N2	94.10 (9)	O8—C13—C14	120.2 (3)
O5i—Nd1—N2	91.07 (8)	N5—C13—C14	115.3 (3)
O4—Nd1—N2	124.59 (9)	C15—C14—C18	118.0 (3)
O4i—Nd1—N2	66.36 (8)	C15—C14—C13	124.7 (3)
O1i—Nd1—N2	157.96 (8)	C18—C14—C13	117.2 (3)
O1—Nd1—N2	25.07 (9)	C14—C15—C16	119.2 (3)
N1—Nd1—N2	69.05 (8)	C14—C15—H15	120.4
N1i—Nd1—N2	101.58 (9)	C16—C15—H15	120.4
N2i—Nd1—N2	168.35 (12)	N6—C16—C15	122.1 (3)
N2—O1—Nd1	95.73 (19)	N6—C16—H16	118.9
C1—N1—C5	115.7 (3)	C15—C16—H16	118.9
C1—N1—Nd1	122.6 (2)	N6—C17—C18	121.8 (3)
C5—N1—Nd1	119.53 (19)	N6—C17—H17	119.1
N1—C1—C2	124.1 (3)	C18—C17—H17	119.1
N1—C1—H1	118.0	C17—C18—C14	119.6 (3)
C2—C1—H1	118.0	C17—C18—H18	120.2
N2—O2—Nd1	97.10 (18)	C14—C18—H18	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1ii	0.89	2.43	3.285 (4)	160
N5—H5A···O7ii	0.89	2.23	2.966 (4)	140
N6—H6···N6iii	0.89	1.86	2.742 (5)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1i	0.89	2.43	3.285 (4)	160
N5—H5A⋯O7i	0.89	2.23	2.966 (4)	140
N6—H6⋯N6ii	0.89	1.86	2.742 (5)	168

Symmetry codes: (i) ; (ii) .